 
data_chai002 

# start Validation Reply Form
_vrf_REFNR01_chai002
;
PROBLEM: Ratio of reflections to parameters is < 6 for a
RESPONSE: See response to THETM01. Despite the low data to 
parameter ratio, the resulting structure makes chemical 
sense and is computationally converged.
;
_vrf_THETM01_chai002
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The compound consistently deposits as thin plates. 
No data were observed beyond 84 degrees (2theta).
;
_vrf_PLAT088_chai002
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.35 Note  
RESPONSE: See response to REFNR01.
;
# end Validation Reply Form
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C35 H37 N O9' 
_chemical_formula_weight          615.65 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/n' 
_space_group_name_Hall            '-P 2yn' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
  
_cell_length_a                    11.0048(3) 
_cell_length_b                    11.2247(3) 
_cell_length_c                    24.9243(7) 
_cell_angle_alpha                 90 
_cell_angle_beta                  93.796(2) 
_cell_angle_gamma                 90 
_cell_volume                      3072.03(15) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     6066 
_cell_measurement_theta_min       3.55 
_cell_measurement_theta_max       43.15 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.331 
_exptl_crystal_F_000              1304 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.337 
_exptl_crystal_size_mid           0.151 
_exptl_crystal_size_min           0.028 
_exptl_absorpt_coefficient_mu     0.792 
_shelx_estimated_absorpt_T_min    0.776 
_shelx_estimated_absorpt_T_max    0.978 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.5986   
_exptl_absorpt_correction_T_max   0.7485 
_exptl_absorpt_process_details    'APEX3 (Bruker, 2015)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       200(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker AXS APEX diffractometer' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.33 
_diffrn_reflns_number             11609 
_diffrn_reflns_av_unetI/netI      0.0278 
_diffrn_reflns_av_R_equivalents   0.0345 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        22 
_diffrn_reflns_theta_min          3.554 
_diffrn_reflns_theta_max          43.266 
_diffrn_reflns_theta_full         43.266 
_diffrn_measured_fraction_theta_max   0.996 
_diffrn_measured_fraction_theta_full  0.996 
_diffrn_reflns_Laue_measured_fraction_max    0.996 
_diffrn_reflns_Laue_measured_fraction_full   0.996 
_diffrn_reflns_point_group_measured_fraction_max   0.996 
_diffrn_reflns_point_group_measured_fraction_full  0.996 
_reflns_number_total              2241 
_reflns_number_gt                 1986 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0597P)²+1.7898P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          2241 
_refine_ls_number_parameters      420 
_refine_ls_number_restraints      5 
_refine_ls_R_factor_all           0.0452 
_refine_ls_R_factor_gt            0.0398 
_refine_ls_wR_factor_ref          0.1076 
_refine_ls_wR_factor_gt           0.1037 
_refine_ls_goodness_of_fit_ref    1.061 
_refine_ls_restrained_S_all       1.060 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.4331(3) 0.2968(3) 0.64341(14) 0.0505(10) Uani 1 1 d . . . . . 
C2 C 0.3053(4) 0.3257(4) 0.61963(18) 0.0628(11) Uani 1 1 d . . . . . 
C3 C 0.2199(4) 0.2533(4) 0.64686(17) 0.0623(11) Uani 1 1 d . . . . . 
H3 H 0.1340 0.2629 0.6436 0.075 Uiso 1 1 calc R U . . . 
C4 C 0.2785(3) 0.1715(4) 0.67704(15) 0.0538(10) Uani 1 1 d . . . . . 
C5 C 0.4142(3) 0.1789(3) 0.67440(14) 0.0469(10) Uani 1 1 d . . . . . 
H5 H 0.4392 0.1121 0.6510 0.056 Uiso 1 1 calc R U . . . 
C6 C 0.2196(3) 0.0770(4) 0.70933(17) 0.0736(12) Uani 1 1 d . . . . . 
H6A H 0.1387 0.0584 0.6916 0.088 Uiso 1 1 calc R U . . . 
H6B H 0.2061 0.1100 0.7453 0.088 Uiso 1 1 calc R U . . . 
C7 C 0.2907(4) -0.0385(3) 0.71680(16) 0.0696(12) Uani 1 1 d . . . . . 
H7A H 0.2338 -0.1030 0.7255 0.084 Uiso 1 1 calc R U . . . 
H7B H 0.3257 -0.0594 0.6824 0.084 Uiso 1 1 calc R U . . . 
C8 C 0.3922(4) -0.0325(4) 0.76052(17) 0.0785(12) Uani 1 1 d . . . . . 
H8A H 0.4167 -0.1148 0.7706 0.094 Uiso 1 1 calc R U . . . 
H8B H 0.3602 0.0052 0.7926 0.094 Uiso 1 1 calc R U . . . 
C9 C 0.5047(4) 0.0354(4) 0.74614(17) 0.0793(13) Uani 1 1 d . . . . . 
H9A H 0.5416 -0.0076 0.7166 0.095 Uiso 1 1 calc R U . . . 
H9B H 0.5645 0.0337 0.7776 0.095 Uiso 1 1 calc R U . . . 
C10 C 0.4855(3) 0.1648(3) 0.72905(16) 0.0668(11) Uani 1 1 d . . . . . 
H10A H 0.5659 0.2037 0.7274 0.080 Uiso 1 1 calc R U . . . 
H10B H 0.4411 0.2067 0.7567 0.080 Uiso 1 1 calc R U . . . 
C11 C 0.4630(4) 0.4001(3) 0.68385(16) 0.0805(13) Uani 1 1 d . . . . . 
H11A H 0.4571 0.4765 0.6648 0.121 Uiso 1 1 calc R U . . . 
H11B H 0.5457 0.3899 0.7002 0.121 Uiso 1 1 calc R U . . . 
H11C H 0.4048 0.3989 0.7120 0.121 Uiso 1 1 calc R U . . . 
C12 C 0.5316(3) 0.3001(3) 0.60161(14) 0.0470(10) Uani 1 1 d . . . . . 
H12 H 0.5541 0.3862 0.5995 0.056 Uiso 1 1 calc R U . . . 
C13 C 0.6641(3) 0.1179(4) 0.61689(14) 0.0558(10) Uani 1 1 d . . . . . 
H13 H 0.6008 0.0712 0.5998 0.067 Uiso 1 1 calc R U . . . 
C14 C 0.7702(5) 0.0638(4) 0.63603(17) 0.0750(12) Uani 1 1 d . . . . . 
H14 H 0.7792 -0.0199 0.6321 0.090 Uiso 1 1 calc R U . . . 
C15 C 0.8630(4) 0.1287(6) 0.66065(19) 0.0896(14) Uani 1 1 d . . . . . 
H15 H 0.9359 0.0906 0.6741 0.107 Uiso 1 1 calc R U . . . 
C16 C 0.8494(5) 0.2500(6) 0.66559(17) 0.0842(13) Uani 1 1 d . . . . . 
H16 H 0.9138 0.2962 0.6821 0.101 Uiso 1 1 calc R U . . . 
C17 C 0.7426(5) 0.3050(4) 0.64678(16) 0.0654(11) Uani 1 1 d . . . . . 
H17 H 0.7342 0.3887 0.6508 0.079 Uiso 1 1 calc R U . . . 
C18 C 0.6480(3) 0.2400(4) 0.62226(13) 0.0479(10) Uani 1 1 d . . . . . 
C19 C 0.5008(3) 0.2641(3) 0.54256(14) 0.0409(9) Uani 1 1 d . . . . . 
C20 C 0.5643(3) 0.3210(3) 0.50384(19) 0.0433(9) Uani 1 1 d . . . . . 
C21 C 0.5524(3) 0.2997(3) 0.44933(18) 0.0489(10) Uani 1 1 d . . . . . 
H21 H 0.5972 0.3441 0.4249 0.059 Uiso 1 1 calc R U . . . 
C22 C 0.4730(4) 0.2114(3) 0.43190(17) 0.0474(10) Uani 1 1 d . . . . . 
C23 C 0.4060(3) 0.1502(3) 0.46811(18) 0.0451(9) Uani 1 1 d . . . . . 
H23 H 0.3501 0.0904 0.4555 0.054 Uiso 1 1 calc R U . . . 
C24 C 0.4203(3) 0.1756(3) 0.52264(17) 0.0406(9) Uani 1 1 d . . . . . 
C25 C 0.7678(4) 0.3866(4) 0.52113(14) 0.0483(10) Uani 1 1 d . . . . . 
C26 C 0.9621(4) 0.4601(3) 0.56237(14) 0.0502(10) Uani 1 1 d . . . . . 
H26 H 0.9925 0.3814 0.5592 0.060 Uiso 1 1 calc R U . . . 
C27 C 1.0368(3) 0.5471(4) 0.58499(14) 0.0517(10) Uani 1 1 d . . . . . 
H27 H 1.1180 0.5295 0.5979 0.062 Uiso 1 1 calc R U . . . 
C28 C 0.9908(4) 0.6607(4) 0.58844(14) 0.0478(10) Uani 1 1 d . . . . . 
C29 C 0.8749(4) 0.6891(3) 0.56970(16) 0.0576(10) Uani 1 1 d . . . . . 
H29 H 0.8462 0.7687 0.5717 0.069 Uiso 1 1 calc R U . . . 
C30 C 0.8001(3) 0.6002(4) 0.54773(14) 0.0505(10) Uani 1 1 d . . . . . 
H30 H 0.7189 0.6183 0.5351 0.061 Uiso 1 1 calc R U . . . 
C31 C 0.8433(3) 0.4850(3) 0.54410(13) 0.0409(9) Uani 1 1 d . . . . . 
C32A C 0.4829(10) 0.2550(15) 0.3377(5) 0.0798(19) Uani 0.792(5) 1 d D . P A 1 
H32A H 0.5663 0.2859 0.3458 0.096 Uiso 0.792(5) 1 calc R U P A 1 
H32B H 0.4823 0.2108 0.3033 0.096 Uiso 0.792(5) 1 calc R U P A 1 
C33A C 0.2857(8) 0.3061(14) 0.3091(8) 0.115(5) Uani 0.792(5) 1 d D . P A 1 
H33A H 0.2925 0.2791 0.2720 0.173 Uiso 0.792(5) 1 calc R U P A 1 
H33B H 0.2279 0.3724 0.3094 0.173 Uiso 0.792(5) 1 calc R U P A 1 
H33C H 0.2568 0.2403 0.3307 0.173 Uiso 0.792(5) 1 calc R U P A 1 
C32B C 0.493(4) 0.264(6) 0.343(2) 0.0798(19) Uani 0.208(5) 1 d D . P A 2 
H32C H 0.4879 0.3438 0.3591 0.096 Uiso 0.208(5) 1 calc R U P A 2 
H32D H 0.5784 0.2489 0.3348 0.096 Uiso 0.208(5) 1 calc R U P A 2 
C33B C 0.312(4) 0.336(7) 0.304(3) 0.115(5) Uani 0.208(5) 1 d D . P A 2 
H33D H 0.2560 0.3305 0.2716 0.173 Uiso 0.208(5) 1 calc R U P A 2 
H33E H 0.3371 0.4191 0.3094 0.173 Uiso 0.208(5) 1 calc R U P A 2 
H33F H 0.2704 0.3082 0.3351 0.173 Uiso 0.208(5) 1 calc R U P A 2 
C34 C 0.2816(3) 0.0168(3) 0.54228(15) 0.0538(10) Uani 1 1 d . . . . . 
H34A H 0.3318 -0.0397 0.5228 0.065 Uiso 1 1 calc R U . . . 
H34B H 0.2539 -0.0248 0.5743 0.065 Uiso 1 1 calc R U . . . 
C35 C 0.0888(3) 0.1110(4) 0.53557(17) 0.0727(12) Uani 1 1 d . . . . . 
H35A H 0.0682 0.0660 0.5674 0.109 Uiso 1 1 calc R U . . . 
H35B H 0.0160 0.1200 0.5111 0.109 Uiso 1 1 calc R U . . . 
H35C H 0.1194 0.1899 0.5466 0.109 Uiso 1 1 calc R U . . . 
N1 N 1.0689(4) 0.7546(4) 0.61291(13) 0.0690(10) Uani 1 1 d . . . . . 
O1 O 1.1722(3) 0.7288(3) 0.62950(12) 0.0895(10) Uani 1 1 d . . . . . 
O2 O 1.0276(3) 0.8547(3) 0.61644(14) 0.1092(12) Uani 1 1 d . . . . . 
O3 O 0.6469(2) 0.41135(18) 0.52155(9) 0.0481(6) Uani 1 1 d . . . . . 
O4 O 0.8069(2) 0.2943(2) 0.50499(10) 0.0649(8) Uani 1 1 d . . . . . 
O5 O 0.4534(2) 0.1755(2) 0.37905(12) 0.0645(7) Uani 1 1 d D . . . . 
O6A O 0.4064(5) 0.3461(3) 0.33185(15) 0.0966(14) Uani 0.792(5) 1 d D . P A 1 
O6B O 0.4215(15) 0.2602(12) 0.2967(6) 0.0966(14) Uani 0.208(5) 1 d D . P A 2 
O7 O 0.3558(2) 0.1167(2) 0.55969(9) 0.0494(6) Uani 1 1 d . . . . . 
O8 O 0.1800(2) 0.04885(19) 0.50892(10) 0.0578(7) Uani 1 1 d . . . . . 
O9 O 0.2823(3) 0.4012(3) 0.58490(13) 0.0887(9) Uani 1 1 d . . . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
C1 C2 1.525(5) . ? 
C1 C12 1.553(5) . ? 
C1 C5 1.553(5) . ? 
C1 C11 1.557(5) . ? 
C2 O9 1.225(4) . ? 
C2 C3 1.445(5) . ? 
C3 C4 1.326(5) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.502(5) . ? 
C4 C6 1.504(5) . ? 
C5 C10 1.534(5) . ? 
C5 H5 1.0000 . ? 
C6 C7 1.520(5) . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
C7 C8 1.510(5) . ? 
C7 H7A 0.9900 . ? 
C7 H7B 0.9900 . ? 
C8 C9 1.517(5) . ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 C10 1.525(5) . ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
C10 H10A 0.9900 . ? 
C10 H10B 0.9900 . ? 
C11 H11A 0.9800 . ? 
C11 H11B 0.9800 . ? 
C11 H11C 0.9800 . ? 
C12 C18 1.508(5) . ? 
C12 C19 1.542(5) . ? 
C12 H12 1.0000 . ? 
C13 C14 1.373(5) . ? 
C13 C18 1.389(5) . ? 
C13 H13 0.9500 . ? 
C14 C15 1.367(6) . ? 
C14 H14 0.9500 . ? 
C15 C16 1.376(6) . ? 
C15 H15 0.9500 . ? 
C16 C17 1.381(6) . ? 
C16 H16 0.9500 . ? 
C17 C18 1.381(5) . ? 
C17 H17 0.9500 . ? 
C19 C20 1.385(5) . ? 
C19 C24 1.400(5) . ? 
C20 C21 1.377(5) . ? 
C20 O3 1.413(4) . ? 
C21 C22 1.373(5) . ? 
C21 H21 0.9500 . ? 
C22 O5 1.381(4) . ? 
C22 C23 1.384(5) . ? 
C23 C24 1.387(4) . ? 
C23 H23 0.9500 . ? 
C24 O7 1.372(4) . ? 
C25 O4 1.202(4) . ? 
C25 O3 1.360(4) . ? 
C25 C31 1.475(5) . ? 
C26 C27 1.373(5) . ? 
C26 C31 1.384(4) . ? 
C26 H26 0.9500 . ? 
C27 C28 1.376(5) . ? 
C27 H27 0.9500 . ? 
C28 C29 1.366(5) . ? 
C28 N1 1.468(5) . ? 
C29 C30 1.383(5) . ? 
C29 H29 0.9500 . ? 
C30 C31 1.382(5) . ? 
C30 H30 0.9500 . ? 
C32A O6A 1.326(17) . ? 
C32A O5 1.417(6) . ? 
C32A H32A 0.9900 . ? 
C32A H32B 0.9900 . ? 
C33A O6A 1.480(15) . ? 
C33A H33A 0.9800 . ? 
C33A H33B 0.9800 . ? 
C33A H33C 0.9800 . ? 
C32B O6B 1.34(3) . ? 
C32B O5 1.431(18) . ? 
C32B H32C 0.9900 . ? 
C32B H32D 0.9900 . ? 
C33B O6B 1.50(3) . ? 
C33B H33D 0.9800 . ? 
C33B H33E 0.9800 . ? 
C33B H33F 0.9800 . ? 
C34 O8 1.396(4) . ? 
C34 O7 1.436(4) . ? 
C34 H34A 0.9900 . ? 
C34 H34B 0.9900 . ? 
C35 O8 1.422(4) . ? 
C35 H35A 0.9800 . ? 
C35 H35B 0.9800 . ? 
C35 H35C 0.9800 . ? 
N1 O2 1.217(4) . ? 
N1 O1 1.219(4) . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2 C1 C12 113.7(3) . . ? 
C2 C1 C5 103.0(3) . . ? 
C12 C1 C5 118.5(3) . . ? 
C2 C1 C11 104.1(3) . . ? 
C12 C1 C11 106.8(3) . . ? 
C5 C1 C11 110.0(3) . . ? 
O9 C2 C3 127.7(4) . . ? 
O9 C2 C1 124.3(4) . . ? 
C3 C2 C1 108.0(4) . . ? 
C4 C3 C2 110.5(4) . . ? 
C4 C3 H3 124.8 . . ? 
C2 C3 H3 124.8 . . ? 
C3 C4 C5 112.6(3) . . ? 
C3 C4 C6 125.6(4) . . ? 
C5 C4 C6 121.8(4) . . ? 
C4 C5 C10 114.0(3) . . ? 
C4 C5 C1 103.6(3) . . ? 
C10 C5 C1 116.9(3) . . ? 
C4 C5 H5 107.3 . . ? 
C10 C5 H5 107.3 . . ? 
C1 C5 H5 107.3 . . ? 
C4 C6 C7 115.5(3) . . ? 
C4 C6 H6A 108.4 . . ? 
C7 C6 H6A 108.4 . . ? 
C4 C6 H6B 108.4 . . ? 
C7 C6 H6B 108.4 . . ? 
H6A C6 H6B 107.5 . . ? 
C8 C7 C6 113.6(3) . . ? 
C8 C7 H7A 108.8 . . ? 
C6 C7 H7A 108.8 . . ? 
C8 C7 H7B 108.8 . . ? 
C6 C7 H7B 108.8 . . ? 
H7A C7 H7B 107.7 . . ? 
C7 C8 C9 115.4(3) . . ? 
C7 C8 H8A 108.4 . . ? 
C9 C8 H8A 108.4 . . ? 
C7 C8 H8B 108.4 . . ? 
C9 C8 H8B 108.4 . . ? 
H8A C8 H8B 107.5 . . ? 
C8 C9 C10 116.4(3) . . ? 
C8 C9 H9A 108.2 . . ? 
C10 C9 H9A 108.2 . . ? 
C8 C9 H9B 108.2 . . ? 
C10 C9 H9B 108.2 . . ? 
H9A C9 H9B 107.4 . . ? 
C9 C10 C5 113.6(3) . . ? 
C9 C10 H10A 108.9 . . ? 
C5 C10 H10A 108.9 . . ? 
C9 C10 H10B 108.9 . . ? 
C5 C10 H10B 108.9 . . ? 
H10A C10 H10B 107.7 . . ? 
C1 C11 H11A 109.5 . . ? 
C1 C11 H11B 109.5 . . ? 
H11A C11 H11B 109.5 . . ? 
C1 C11 H11C 109.5 . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
C18 C12 C19 109.7(3) . . ? 
C18 C12 C1 112.0(3) . . ? 
C19 C12 C1 121.0(3) . . ? 
C18 C12 H12 104.1 . . ? 
C19 C12 H12 104.1 . . ? 
C1 C12 H12 104.1 . . ? 
C14 C13 C18 120.9(4) . . ? 
C14 C13 H13 119.6 . . ? 
C18 C13 H13 119.6 . . ? 
C15 C14 C13 120.9(4) . . ? 
C15 C14 H14 119.6 . . ? 
C13 C14 H14 119.6 . . ? 
C14 C15 C16 119.0(4) . . ? 
C14 C15 H15 120.5 . . ? 
C16 C15 H15 120.5 . . ? 
C15 C16 C17 120.5(4) . . ? 
C15 C16 H16 119.8 . . ? 
C17 C16 H16 119.8 . . ? 
C18 C17 C16 120.9(4) . . ? 
C18 C17 H17 119.5 . . ? 
C16 C17 H17 119.5 . . ? 
C17 C18 C13 117.8(3) . . ? 
C17 C18 C12 120.9(4) . . ? 
C13 C18 C12 121.3(3) . . ? 
C20 C19 C24 114.7(3) . . ? 
C20 C19 C12 117.1(3) . . ? 
C24 C19 C12 128.2(3) . . ? 
C21 C20 C19 126.0(3) . . ? 
C21 C20 O3 116.7(4) . . ? 
C19 C20 O3 117.2(4) . . ? 
C22 C21 C20 117.0(3) . . ? 
C22 C21 H21 121.5 . . ? 
C20 C21 H21 121.5 . . ? 
C21 C22 O5 124.6(4) . . ? 
C21 C22 C23 120.5(4) . . ? 
O5 C22 C23 114.9(4) . . ? 
C22 C23 C24 120.4(3) . . ? 
C22 C23 H23 119.8 . . ? 
C24 C23 H23 119.8 . . ? 
O7 C24 C23 122.0(3) . . ? 
O7 C24 C19 116.6(4) . . ? 
C23 C24 C19 121.4(3) . . ? 
O4 C25 O3 123.4(3) . . ? 
O4 C25 C31 124.8(4) . . ? 
O3 C25 C31 111.8(4) . . ? 
C27 C26 C31 121.2(3) . . ? 
C27 C26 H26 119.4 . . ? 
C31 C26 H26 119.4 . . ? 
C26 C27 C28 118.1(3) . . ? 
C26 C27 H27 120.9 . . ? 
C28 C27 H27 120.9 . . ? 
C29 C28 C27 122.3(3) . . ? 
C29 C28 N1 118.8(4) . . ? 
C27 C28 N1 118.9(4) . . ? 
C28 C29 C30 118.9(3) . . ? 
C28 C29 H29 120.5 . . ? 
C30 C29 H29 120.5 . . ? 
C29 C30 C31 120.2(3) . . ? 
C29 C30 H30 119.9 . . ? 
C31 C30 H30 119.9 . . ? 
C30 C31 C26 119.3(3) . . ? 
C30 C31 C25 122.6(4) . . ? 
C26 C31 C25 118.2(4) . . ? 
O6A C32A O5 113.0(12) . . ? 
O6A C32A H32A 109.0 . . ? 
O5 C32A H32A 109.0 . . ? 
O6A C32A H32B 109.0 . . ? 
O5 C32A H32B 109.0 . . ? 
H32A C32A H32B 107.8 . . ? 
O6A C33A H33A 109.5 . . ? 
O6A C33A H33B 109.5 . . ? 
H33A C33A H33B 109.5 . . ? 
O6A C33A H33C 109.5 . . ? 
H33A C33A H33C 109.5 . . ? 
H33B C33A H33C 109.5 . . ? 
O6B C32B O5 110(2) . . ? 
O6B C32B H32C 109.7 . . ? 
O5 C32B H32C 109.7 . . ? 
O6B C32B H32D 109.7 . . ? 
O5 C32B H32D 109.7 . . ? 
H32C C32B H32D 108.2 . . ? 
O6B C33B H33D 109.5 . . ? 
O6B C33B H33E 109.5 . . ? 
H33D C33B H33E 109.5 . . ? 
O6B C33B H33F 109.5 . . ? 
H33D C33B H33F 109.5 . . ? 
H33E C33B H33F 109.5 . . ? 
O8 C34 O7 113.3(3) . . ? 
O8 C34 H34A 108.9 . . ? 
O7 C34 H34A 108.9 . . ? 
O8 C34 H34B 108.9 . . ? 
O7 C34 H34B 108.9 . . ? 
H34A C34 H34B 107.7 . . ? 
O8 C35 H35A 109.5 . . ? 
O8 C35 H35B 109.5 . . ? 
H35A C35 H35B 109.5 . . ? 
O8 C35 H35C 109.5 . . ? 
H35A C35 H35C 109.5 . . ? 
H35B C35 H35C 109.5 . . ? 
O2 N1 O1 122.6(4) . . ? 
O2 N1 C28 118.8(4) . . ? 
O1 N1 C28 118.5(4) . . ? 
C25 O3 C20 117.4(3) . . ? 
C22 O5 C32A 118.8(8) . . ? 
C22 O5 C32B 112(3) . . ? 
C32A O6A C33A 110.8(8) . . ? 
C32B O6B C33B 108(2) . . ? 
C24 O7 C34 118.8(3) . . ? 
C34 O8 C35 114.2(3) . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C12 C1 C2 O9 -38.0(5) . . . . ? 
C5 C1 C2 O9 -167.4(3) . . . . ? 
C11 C1 C2 O9 77.8(4) . . . . ? 
C12 C1 C2 C3 144.4(3) . . . . ? 
C5 C1 C2 C3 15.1(4) . . . . ? 
C11 C1 C2 C3 -99.7(3) . . . . ? 
O9 C2 C3 C4 172.3(4) . . . . ? 
C1 C2 C3 C4 -10.3(4) . . . . ? 
C2 C3 C4 C5 0.5(4) . . . . ? 
C2 C3 C4 C6 -177.2(3) . . . . ? 
C3 C4 C5 C10 137.2(3) . . . . ? 
C6 C4 C5 C10 -44.9(5) . . . . ? 
C3 C4 C5 C1 9.1(4) . . . . ? 
C6 C4 C5 C1 -173.0(3) . . . . ? 
C2 C1 C5 C4 -14.1(3) . . . . ? 
C12 C1 C5 C4 -140.5(3) . . . . ? 
C11 C1 C5 C4 96.3(3) . . . . ? 
C2 C1 C5 C10 -140.4(3) . . . . ? 
C12 C1 C5 C10 93.2(4) . . . . ? 
C11 C1 C5 C10 -30.0(4) . . . . ? 
C3 C4 C6 C7 150.1(4) . . . . ? 
C5 C4 C6 C7 -27.5(5) . . . . ? 
C4 C6 C7 C8 80.1(4) . . . . ? 
C6 C7 C8 C9 -75.5(5) . . . . ? 
C7 C8 C9 C10 57.8(5) . . . . ? 
C8 C9 C10 C5 -69.1(5) . . . . ? 
C4 C5 C10 C9 82.6(4) . . . . ? 
C1 C5 C10 C9 -156.4(3) . . . . ? 
C2 C1 C12 C18 -164.5(3) . . . . ? 
C5 C1 C12 C18 -43.5(4) . . . . ? 
C11 C1 C12 C18 81.3(4) . . . . ? 
C2 C1 C12 C19 -32.7(4) . . . . ? 
C5 C1 C12 C19 88.3(4) . . . . ? 
C11 C1 C12 C19 -146.9(3) . . . . ? 
C18 C13 C14 C15 -0.3(6) . . . . ? 
C13 C14 C15 C16 -0.7(6) . . . . ? 
C14 C15 C16 C17 1.1(7) . . . . ? 
C15 C16 C17 C18 -0.6(6) . . . . ? 
C16 C17 C18 C13 -0.4(5) . . . . ? 
C16 C17 C18 C12 -179.8(3) . . . . ? 
C14 C13 C18 C17 0.8(5) . . . . ? 
C14 C13 C18 C12 -179.7(3) . . . . ? 
C19 C12 C18 C17 128.2(3) . . . . ? 
C1 C12 C18 C17 -94.5(4) . . . . ? 
C19 C12 C18 C13 -51.2(4) . . . . ? 
C1 C12 C18 C13 86.0(4) . . . . ? 
C18 C12 C19 C20 -78.7(3) . . . . ? 
C1 C12 C19 C20 148.5(3) . . . . ? 
C18 C12 C19 C24 97.7(4) . . . . ? 
C1 C12 C19 C24 -35.1(5) . . . . ? 
C24 C19 C20 C21 1.4(5) . . . . ? 
C12 C19 C20 C21 178.4(3) . . . . ? 
C24 C19 C20 O3 179.9(2) . . . . ? 
C12 C19 C20 O3 -3.2(4) . . . . ? 
C19 C20 C21 C22 -2.0(5) . . . . ? 
O3 C20 C21 C22 179.5(3) . . . . ? 
C20 C21 C22 O5 -177.5(3) . . . . ? 
C20 C21 C22 C23 1.9(5) . . . . ? 
C21 C22 C23 C24 -1.3(5) . . . . ? 
O5 C22 C23 C24 178.1(3) . . . . ? 
C22 C23 C24 O7 -179.9(3) . . . . ? 
C22 C23 C24 C19 0.8(4) . . . . ? 
C20 C19 C24 O7 179.8(2) . . . . ? 
C12 C19 C24 O7 3.3(4) . . . . ? 
C20 C19 C24 C23 -0.8(4) . . . . ? 
C12 C19 C24 C23 -177.2(3) . . . . ? 
C31 C26 C27 C28 -0.8(5) . . . . ? 
C26 C27 C28 C29 -0.8(5) . . . . ? 
C26 C27 C28 N1 179.5(3) . . . . ? 
C27 C28 C29 C30 1.7(5) . . . . ? 
N1 C28 C29 C30 -178.6(3) . . . . ? 
C28 C29 C30 C31 -1.1(5) . . . . ? 
C29 C30 C31 C26 -0.4(5) . . . . ? 
C29 C30 C31 C25 179.9(3) . . . . ? 
C27 C26 C31 C30 1.3(5) . . . . ? 
C27 C26 C31 C25 -179.0(3) . . . . ? 
O4 C25 C31 C30 160.8(3) . . . . ? 
O3 C25 C31 C30 -20.8(4) . . . . ? 
O4 C25 C31 C26 -18.9(5) . . . . ? 
O3 C25 C31 C26 159.5(3) . . . . ? 
C29 C28 N1 O2 1.0(5) . . . . ? 
C27 C28 N1 O2 -179.2(3) . . . . ? 
C29 C28 N1 O1 -179.9(3) . . . . ? 
C27 C28 N1 O1 -0.2(5) . . . . ? 
O4 C25 O3 C20 2.5(5) . . . . ? 
C31 C25 O3 C20 -176.0(3) . . . . ? 
C21 C20 O3 C25 -73.8(4) . . . . ? 
C19 C20 O3 C25 107.7(3) . . . . ? 
C21 C22 O5 C32A -21.8(8) . . . . ? 
C23 C22 O5 C32A 158.8(7) . . . . ? 
C21 C22 O5 C32B -19(3) . . . . ? 
C23 C22 O5 C32B 161(3) . . . . ? 
O6A C32A O5 C22 -71.8(8) . . . . ? 
O6B C32B O5 C22 -148(4) . . . . ? 
O5 C32A O6A C33A -70.1(11) . . . . ? 
O5 C32B O6B C33B 86(6) . . . . ? 
C23 C24 O7 C34 7.1(4) . . . . ? 
C19 C24 O7 C34 -173.5(3) . . . . ? 
O8 C34 O7 C24 -69.2(3) . . . . ? 
O7 C34 O8 C35 -70.3(3) . . . . ? 
  
_refine_diff_density_max    0.131 
_refine_diff_density_min   -0.152 
_refine_diff_density_rms    0.032 
  
  
  

 
data_chai025_a 
  
_audit_creation_method            'SHELXL-2017/1' 
_shelx_SHELXL_version_number      '2017/1' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
 'C25 H27 Br O3'  
_chemical_formula_sum 
 'C25 H27 Br O3' 
_chemical_formula_weight          455.37 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Br'  'Br'  -0.6763   1.2805 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       triclinic 
_space_group_IT_number            2 
_space_group_name_H-M_alt         'P -1' 
_space_group_name_Hall            '-P 1' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, -y, -z' 
  
_cell_length_a                    9.5143(5) 
_cell_length_b                    10.2624(5) 
_cell_length_c                    11.3217(6) 
_cell_angle_alpha                 81.827(2) 
_cell_angle_beta                  85.407(2) 
_cell_angle_gamma                 81.442(2) 
_cell_volume                      1080.07(10) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     9612 
_cell_measurement_theta_min       3.95 
_cell_measurement_theta_max       75.15 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.400 
_exptl_crystal_F_000              472 
_exptl_transmission_factor_min    0.6080 
_exptl_transmission_factor_max    0.7539
_exptl_crystal_size_max           0.354 
_exptl_crystal_size_mid           0.247 
_exptl_crystal_size_min           0.160 
_exptl_absorpt_coefficient_mu     2.773 
_shelx_estimated_absorpt_T_min    0.440 
_shelx_estimated_absorpt_T_max    0.665 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    'APEX3 (Bruker, 2015)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       200(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker AXS APEX diffractometer' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.33 
_diffrn_reflns_number             26833 
_diffrn_reflns_av_unetI/netI      0.0211 
_diffrn_reflns_av_R_equivalents   0.0282 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          3.952 
_diffrn_reflns_theta_max          75.434 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.958 
_diffrn_measured_fraction_theta_full  0.968 
_diffrn_reflns_Laue_measured_fraction_max    0.958 
_diffrn_reflns_Laue_measured_fraction_full   0.968 
_diffrn_reflns_point_group_measured_fraction_max   0.958 
_diffrn_reflns_point_group_measured_fraction_full  0.968 
_reflns_number_total              4277 
_reflns_number_gt                 4052 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)' 
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.1350P)²+1.8499P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          4277 
_refine_ls_number_parameters      266 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0445 
_refine_ls_R_factor_gt            0.0427 
_refine_ls_wR_factor_ref          0.1377 
_refine_ls_wR_factor_gt           0.1339 
_refine_ls_goodness_of_fit_ref    0.722 
_refine_ls_restrained_S_all       0.722 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Br1 Br 0.52522(3) 0.32581(3) 0.37494(3) 0.04884(15) Uani 1 1 d . . . . . 
O1 O 0.21327(18) 0.83766(18) 0.10008(16) 0.0354(4) Uani 1 1 d . . . . . 
O2 O 0.1431(2) 0.15257(18) 0.17309(17) 0.0386(4) Uani 1 1 d . . . . . 
O3 O 0.0980(2) 0.62249(19) 0.1432(2) 0.0416(4) Uani 1 1 d . . . . . 
H3 H 0.145(3) 0.679(3) 0.139(3) 0.062 Uiso 1 1 calc R U . . . 
C1 C 0.3337(2) 0.8326(2) 0.13388(19) 0.0280(4) Uani 1 1 d . . . . . 
C2 C 0.4158(2) 0.9428(2) 0.12307(19) 0.0296(5) Uani 1 1 d . . . . . 
H2 H 0.386606 1.029126 0.082785 0.036 Uiso 1 1 calc R U . . . 
C3 C 0.5382(2) 0.9063(2) 0.17754(18) 0.0272(4) Uani 1 1 d . . . . . 
C4 C 0.6495(3) 0.9943(3) 0.1796(2) 0.0349(5) Uani 1 1 d . . . . . 
H4A H 0.602576 1.087697 0.170965 0.042 Uiso 1 1 calc R U . . . 
H4B H 0.716580 0.984176 0.108930 0.042 Uiso 1 1 calc R U . . . 
C25 C 0.0265(3) 0.1635(3) 0.0988(3) 0.0431(6) Uani 1 1 d . . . . . 
H00A H -0.059094 0.209395 0.137061 0.065 Uiso 1 1 calc R U . . . 
H00B H 0.009554 0.074412 0.087021 0.065 Uiso 1 1 calc R U . . . 
H00C H 0.048899 0.214053 0.021147 0.065 Uiso 1 1 calc R U . . . 
C5 C 0.7354(3) 0.9697(3) 0.2907(2) 0.0394(6) Uani 1 1 d . . . . . 
H5A H 0.780965 1.049334 0.295198 0.047 Uiso 1 1 calc R U . . . 
H5B H 0.669412 0.957621 0.362344 0.047 Uiso 1 1 calc R U . . . 
C6 C 0.8496(3) 0.8494(3) 0.2934(3) 0.0455(6) Uani 1 1 d . . . . . 
H6A H 0.917967 0.856462 0.352901 0.055 Uiso 1 1 calc R U . . . 
H6B H 0.902246 0.852398 0.214223 0.055 Uiso 1 1 calc R U . . . 
C7 C 0.7967(3) 0.7139(3) 0.3235(3) 0.0443(6) Uani 1 1 d . . . . . 
H7A H 0.880571 0.644020 0.328461 0.053 Uiso 1 1 calc R U . . . 
H7B H 0.746284 0.710048 0.403595 0.053 Uiso 1 1 calc R U . . . 
C8 C 0.6974(2) 0.6812(3) 0.2353(3) 0.0378(5) Uani 1 1 d . . . . . 
H8A H 0.686266 0.585883 0.253242 0.045 Uiso 1 1 calc R U . . . 
H8B H 0.741965 0.696036 0.153335 0.045 Uiso 1 1 calc R U . . . 
C9 C 0.5490(2) 0.7647(2) 0.23921(19) 0.0267(4) Uani 1 1 d . . . . . 
H9 H 0.520959 0.770454 0.325543 0.032 Uiso 1 1 calc R U . . . 
C10 C 0.4264(2) 0.7071(2) 0.18816(19) 0.0258(4) Uani 1 1 d . . . . . 
C11 C 0.4838(3) 0.6332(3) 0.0809(2) 0.0360(5) Uani 1 1 d . . . . . 
H11A H 0.541793 0.549184 0.109553 0.054 Uiso 1 1 calc R U . . . 
H11B H 0.542256 0.688505 0.025685 0.054 Uiso 1 1 calc R U . . . 
H11C H 0.403754 0.614909 0.039439 0.054 Uiso 1 1 calc R U . . . 
C12 C 0.3530(2) 0.6122(2) 0.28781(18) 0.0247(4) Uani 1 1 d . . . . . 
H12 H 0.433678 0.569043 0.337563 0.030 Uiso 1 1 calc R U . . . 
C13 C 0.2381(2) 0.8151(2) 0.3899(2) 0.0286(4) Uani 1 1 d . . . . . 
H13 H 0.290737 0.870864 0.334639 0.034 Uiso 1 1 calc R U . . . 
C14 C 0.1521(3) 0.8698(3) 0.4812(2) 0.0327(5) Uani 1 1 d . . . . . 
H14 H 0.146287 0.961804 0.487388 0.039 Uiso 1 1 calc R U . . . 
C15 C 0.0754(3) 0.7902(3) 0.5626(2) 0.0370(5) Uani 1 1 d . . . . . 
H15 H 0.017173 0.826916 0.625233 0.044 Uiso 1 1 calc R U . . . 
C16 C 0.0840(3) 0.6569(3) 0.5524(2) 0.0402(6) Uani 1 1 d . . . . . 
H16 H 0.030965 0.601835 0.608009 0.048 Uiso 1 1 calc R U . . . 
C17 C 0.1694(3) 0.6025(3) 0.4614(2) 0.0337(5) Uani 1 1 d . . . . . 
H17 H 0.174329 0.510390 0.455777 0.040 Uiso 1 1 calc R U . . . 
C18 C 0.2486(2) 0.6810(2) 0.37774(18) 0.0255(4) Uani 1 1 d . . . . . 
C19 C 0.2974(2) 0.4938(2) 0.24836(19) 0.0262(4) Uani 1 1 d . . . . . 
C20 C 0.3597(2) 0.3629(2) 0.2836(2) 0.0302(5) Uani 1 1 d . . . . . 
C21 C 0.3082(3) 0.2508(2) 0.2591(2) 0.0334(5) Uani 1 1 d . . . . . 
H21 H 0.353664 0.164395 0.287094 0.040 Uiso 1 1 calc R U . . . 
C22 C 0.1884(3) 0.2675(2) 0.1925(2) 0.0304(5) Uani 1 1 d . . . . . 
C23 C 0.1229(2) 0.3941(2) 0.1533(2) 0.0309(5) Uani 1 1 d . . . . . 
H23 H 0.041896 0.405713 0.106974 0.037 Uiso 1 1 calc R U . . . 
C24 C 0.1758(2) 0.5048(2) 0.1819(2) 0.0289(4) Uani 1 1 d . . . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Br1 C20 1.914(2) . ? 
O1 C1 1.229(3) . ? 
O2 C22 1.366(3) . ? 
O2 C25 1.427(3) . ? 
O3 C24 1.354(3) . ? 
O3 H3 0.78(5) . ? 
C1 C2 1.453(3) . ? 
C1 C10 1.529(3) . ? 
C2 C3 1.340(3) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.494(3) . ? 
C3 C9 1.513(3) . ? 
C4 C5 1.526(3) . ? 
C4 H4A 0.9900 . ? 
C4 H4B 0.9900 . ? 
C25 H00A 0.9800 . ? 
C25 H00B 0.9800 . ? 
C25 H00C 0.9800 . ? 
C5 C6 1.517(4) . ? 
C5 H5A 0.9900 . ? 
C5 H5B 0.9900 . ? 
C6 C7 1.532(4) . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
C7 C8 1.531(4) . ? 
C7 H7A 0.9900 . ? 
C7 H7B 0.9900 . ? 
C8 C9 1.539(3) . ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 C10 1.567(3) . ? 
C9 H9 1.0000 . ? 
C10 C11 1.543(3) . ? 
C10 C12 1.573(3) . ? 
C11 H11A 0.9800 . ? 
C11 H11B 0.9800 . ? 
C11 H11C 0.9800 . ? 
C12 C19 1.529(3) . ? 
C12 C18 1.535(3) . ? 
C12 H12 1.0000 . ? 
C13 C18 1.391(3) . ? 
C13 C14 1.395(3) . ? 
C13 H13 0.9500 . ? 
C14 C15 1.380(4) . ? 
C14 H14 0.9500 . ? 
C15 C16 1.379(4) . ? 
C15 H15 0.9500 . ? 
C16 C17 1.389(4) . ? 
C16 H16 0.9500 . ? 
C17 C18 1.401(3) . ? 
C17 H17 0.9500 . ? 
C19 C20 1.401(3) . ? 
C19 C24 1.412(3) . ? 
C20 C21 1.386(3) . ? 
C21 C22 1.393(3) . ? 
C21 H21 0.9500 . ? 
C22 C23 1.383(3) . ? 
C23 C24 1.397(3) . ? 
C23 H23 0.9500 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C22 O2 C25 117.7(2) . . ? 
C24 O3 H3 109.5 . . ? 
O1 C1 C2 126.1(2) . . ? 
O1 C1 C10 125.6(2) . . ? 
C2 C1 C10 108.20(19) . . ? 
C3 C2 C1 110.9(2) . . ? 
C3 C2 H2 124.5 . . ? 
C1 C2 H2 124.5 . . ? 
C2 C3 C4 124.7(2) . . ? 
C2 C3 C9 111.50(19) . . ? 
C4 C3 C9 123.8(2) . . ? 
C3 C4 C5 116.2(2) . . ? 
C3 C4 H4A 108.2 . . ? 
C5 C4 H4A 108.2 . . ? 
C3 C4 H4B 108.2 . . ? 
C5 C4 H4B 108.2 . . ? 
H4A C4 H4B 107.4 . . ? 
O2 C25 H00A 109.5 . . ? 
O2 C25 H00B 109.5 . . ? 
H00A C25 H00B 109.5 . . ? 
O2 C25 H00C 109.5 . . ? 
H00A C25 H00C 109.5 . . ? 
H00B C25 H00C 109.5 . . ? 
C6 C5 C4 113.9(2) . . ? 
C6 C5 H5A 108.8 . . ? 
C4 C5 H5A 108.8 . . ? 
C6 C5 H5B 108.8 . . ? 
C4 C5 H5B 108.8 . . ? 
H5A C5 H5B 107.7 . . ? 
C5 C6 C7 115.7(2) . . ? 
C5 C6 H6A 108.3 . . ? 
C7 C6 H6A 108.3 . . ? 
C5 C6 H6B 108.3 . . ? 
C7 C6 H6B 108.3 . . ? 
H6A C6 H6B 107.4 . . ? 
C8 C7 C6 115.7(2) . . ? 
C8 C7 H7A 108.3 . . ? 
C6 C7 H7A 108.3 . . ? 
C8 C7 H7B 108.3 . . ? 
C6 C7 H7B 108.3 . . ? 
H7A C7 H7B 107.4 . . ? 
C7 C8 C9 113.4(2) . . ? 
C7 C8 H8A 108.9 . . ? 
C9 C8 H8A 108.9 . . ? 
C7 C8 H8B 108.9 . . ? 
C9 C8 H8B 108.9 . . ? 
H8A C8 H8B 107.7 . . ? 
C3 C9 C8 116.66(19) . . ? 
C3 C9 C10 103.89(18) . . ? 
C8 C9 C10 116.51(19) . . ? 
C3 C9 H9 106.3 . . ? 
C8 C9 H9 106.3 . . ? 
C10 C9 H9 106.3 . . ? 
C1 C10 C11 104.87(19) . . ? 
C1 C10 C9 102.54(18) . . ? 
C11 C10 C9 110.56(18) . . ? 
C1 C10 C12 117.01(17) . . ? 
C11 C10 C12 110.48(19) . . ? 
C9 C10 C12 110.96(17) . . ? 
C10 C11 H11A 109.5 . . ? 
C10 C11 H11B 109.5 . . ? 
H11A C11 H11B 109.5 . . ? 
C10 C11 H11C 109.5 . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
C19 C12 C18 112.35(17) . . ? 
C19 C12 C10 117.11(17) . . ? 
C18 C12 C10 115.80(18) . . ? 
C19 C12 H12 103.0 . . ? 
C18 C12 H12 103.0 . . ? 
C10 C12 H12 103.0 . . ? 
C18 C13 C14 121.6(2) . . ? 
C18 C13 H13 119.2 . . ? 
C14 C13 H13 119.2 . . ? 
C15 C14 C13 120.0(2) . . ? 
C15 C14 H14 120.0 . . ? 
C13 C14 H14 120.0 . . ? 
C16 C15 C14 119.5(2) . . ? 
C16 C15 H15 120.3 . . ? 
C14 C15 H15 120.3 . . ? 
C15 C16 C17 120.5(2) . . ? 
C15 C16 H16 119.7 . . ? 
C17 C16 H16 119.7 . . ? 
C16 C17 C18 121.2(2) . . ? 
C16 C17 H17 119.4 . . ? 
C18 C17 H17 119.4 . . ? 
C13 C18 C17 117.3(2) . . ? 
C13 C18 C12 123.92(19) . . ? 
C17 C18 C12 118.5(2) . . ? 
C20 C19 C24 114.4(2) . . ? 
C20 C19 C12 121.45(19) . . ? 
C24 C19 C12 124.0(2) . . ? 
C21 C20 C19 124.5(2) . . ? 
C21 C20 Br1 114.34(18) . . ? 
C19 C20 Br1 121.16(17) . . ? 
C20 C21 C22 118.7(2) . . ? 
C20 C21 H21 120.7 . . ? 
C22 C21 H21 120.7 . . ? 
O2 C22 C23 124.9(2) . . ? 
O2 C22 C21 115.3(2) . . ? 
C23 C22 C21 119.9(2) . . ? 
C22 C23 C24 120.0(2) . . ? 
C22 C23 H23 120.0 . . ? 
C24 C23 H23 120.0 . . ? 
O3 C24 C23 114.1(2) . . ? 
O3 C24 C19 123.4(2) . . ? 
C23 C24 C19 122.6(2) . . ? 
  
_refine_diff_density_max    1.559 
_refine_diff_density_min   -1.526 
_refine_diff_density_rms    0.086 
  
  
  


 
data_chai014 
  
_audit_creation_method            'SHELXL-2017/1' 
_shelx_SHELXL_version_number      '2017/1' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
 'C10 H14 O'
_chemical_formula_sum 
 'C10 H14 O' 
_chemical_formula_weight          150.21 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       orthorhombic 
_space_group_IT_number            19 
_space_group_name_H-M_alt         'P 21 21 21' 
_space_group_name_Hall            'P 2ac 2ab' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 'x+1/2, -y+1/2, -z' 
 '-x, y+1/2, -z+1/2' 
 '-x+1/2, -y, z+1/2' 
  
_cell_length_a                    8.5999(3) 
_cell_length_b                    9.3027(3) 
_cell_length_c                    11.1004(4) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      888.06(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     8151 
_cell_measurement_theta_min       6.21 
_cell_measurement_theta_max       75.25 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.123 
_exptl_crystal_F_000              328 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.388 
_exptl_crystal_size_mid           0.310 
_exptl_crystal_size_min           0.202 
_exptl_absorpt_coefficient_mu     0.546 
_shelx_estimated_absorpt_T_min    0.816 
_shelx_estimated_absorpt_T_max    0.898 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6943   
_exptl_absorpt_correction_T_max   0.7539 
_exptl_absorpt_process_details    'APEX3 (Bruker, 2015)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       200(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker AXS APEX diffractometer' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.33 
_diffrn_reflns_number             8563 
_diffrn_reflns_av_unetI/netI      0.0245 
_diffrn_reflns_av_R_equivalents   0.0246 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -13 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          6.207 
_diffrn_reflns_theta_max          75.240 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.994 
_diffrn_measured_fraction_theta_full  0.997 
_diffrn_reflns_Laue_measured_fraction_max    0.994 
_diffrn_reflns_Laue_measured_fraction_full   0.997 
_diffrn_reflns_point_group_measured_fraction_max   0.991 
_diffrn_reflns_point_group_measured_fraction_full  0.997 
_reflns_number_total              1822 
_reflns_number_gt                 1807 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.695 
_reflns_Friedel_fraction_max      0.985 
_reflns_Friedel_fraction_full     0.997 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)' 
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0646P)²+0.0611P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    difmap 
_refine_ls_hydrogen_treatment     refall 
_refine_ls_extinction_method      'SHELXL-2017/1 (Sheldrick 2017)' 
_refine_ls_extinction_coef        0.035(5) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 739 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    -0.04(7) 
_chemical_absolute_configuration  ad 
_refine_ls_number_reflns          1822 
_refine_ls_number_parameters      157 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0367 
_refine_ls_R_factor_gt            0.0365 
_refine_ls_wR_factor_ref          0.0947 
_refine_ls_wR_factor_gt           0.0942 
_refine_ls_goodness_of_fit_ref    1.068 
_refine_ls_restrained_S_all       1.068 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.2478(2) 0.87466(16) 0.38557(14) 0.0704(5) Uani 1 1 d . . . . . 
C1 C 0.33353(16) 0.58004(15) 0.67012(12) 0.0335(3) Uani 1 1 d . . . . . 
C2 C 0.30446(16) 0.56701(16) 0.53637(12) 0.0334(3) Uani 1 1 d . . . . . 
C3 C 0.17526(19) 0.65563(16) 0.48141(15) 0.0412(4) Uani 1 1 d . . . . . 
C4 C 0.22354(19) 0.81210(18) 0.48059(17) 0.0463(4) Uani 1 1 d . . . . . 
C5 C 0.2417(2) 0.88873(17) 0.5959(2) 0.0526(4) Uani 1 1 d . . . . . 
C6 C 0.2428(2) 0.83419(18) 0.70691(17) 0.0496(4) Uani 1 1 d . . . . . 
C7 C 0.2299(2) 0.67893(18) 0.74286(14) 0.0445(4) Uani 1 1 d . . . . . 
C8 C 0.27713(17) 0.43894(15) 0.61805(12) 0.0345(3) Uani 1 1 d . . . . . 
C9 C 0.3970(2) 0.32027(18) 0.60942(17) 0.0472(4) Uani 1 1 d . . . . . 
C10 C 0.1157(2) 0.3843(2) 0.64379(18) 0.0494(4) Uani 1 1 d . . . . . 
H1 H 0.441(2) 0.586(2) 0.6945(17) 0.040(5) Uiso 1 1 d . . . . . 
H2 H 0.394(3) 0.559(2) 0.4871(19) 0.051(5) Uiso 1 1 d . . . . . 
H3A H 0.077(2) 0.649(2) 0.5302(17) 0.043(5) Uiso 1 1 d . . . . . 
H3B H 0.153(3) 0.624(3) 0.396(2) 0.060(6) Uiso 1 1 d . . . . . 
H5 H 0.265(4) 0.992(3) 0.589(2) 0.077(8) Uiso 1 1 d . . . . . 
H6 H 0.251(3) 0.899(2) 0.772(2) 0.061(6) Uiso 1 1 d . . . . . 
H7A H 0.125(3) 0.651(2) 0.7344(19) 0.047(5) Uiso 1 1 d . . . . . 
H7B H 0.259(3) 0.669(2) 0.831(2) 0.057(6) Uiso 1 1 d . . . . . 
H8A H 0.041(3) 0.453(3) 0.646(2) 0.066(7) Uiso 1 1 d . . . . . 
H8B H 0.111(3) 0.336(3) 0.722(3) 0.080(8) Uiso 1 1 d . . . . . 
H8C H 0.084(4) 0.309(4) 0.584(3) 0.089(9) Uiso 1 1 d . . . . . 
H8D H 0.404(3) 0.263(3) 0.683(2) 0.054(6) Uiso 1 1 d . . . . . 
H8E H 0.501(3) 0.362(2) 0.5901(19) 0.051(5) Uiso 1 1 d . . . . . 
H9C H 0.366(3) 0.254(3) 0.540(2) 0.076(8) Uiso 1 1 d . . . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C4 1.223(2) . ? 
C1 C2 1.5105(17) . ? 
C1 C8 1.5140(19) . ? 
C1 C7 1.514(2) . ? 
C1 H1 0.96(2) . ? 
C2 C3 1.512(2) . ? 
C2 C8 1.5156(19) . ? 
C2 H2 0.95(2) . ? 
C3 C4 1.514(2) . ? 
C3 H3A 1.00(2) . ? 
C3 H3B 1.01(2) . ? 
C4 C5 1.473(3) . ? 
C5 C6 1.333(3) . ? 
C5 H5 0.98(3) . ? 
C6 C7 1.503(2) . ? 
C6 H6 0.94(2) . ? 
C7 H7A 0.95(2) . ? 
C7 H7B 1.02(2) . ? 
C8 C10 1.506(2) . ? 
C8 C9 1.513(2) . ? 
C9 H8D 0.98(2) . ? 
C9 H8E 1.00(2) . ? 
C9 H9C 1.02(3) . ? 
C10 H8A 0.90(3) . ? 
C10 H8B 0.98(3) . ? 
C10 H8C 1.01(3) . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2 C1 C8 60.15(9) . . ? 
C2 C1 C7 118.39(13) . . ? 
C8 C1 C7 122.80(13) . . ? 
C2 C1 H1 116.0(11) . . ? 
C8 C1 H1 117.8(11) . . ? 
C7 C1 H1 112.2(11) . . ? 
C1 C2 C3 118.32(12) . . ? 
C1 C2 C8 60.04(9) . . ? 
C3 C2 C8 123.78(13) . . ? 
C1 C2 H2 116.0(13) . . ? 
C3 C2 H2 114.1(13) . . ? 
C8 C2 H2 114.0(13) . . ? 
C2 C3 C4 108.98(12) . . ? 
C2 C3 H3A 111.4(11) . . ? 
C4 C3 H3A 107.1(12) . . ? 
C2 C3 H3B 110.9(14) . . ? 
C4 C3 H3B 109.1(14) . . ? 
H3A C3 H3B 109.2(19) . . ? 
O1 C4 C5 120.05(17) . . ? 
O1 C4 C3 120.65(17) . . ? 
C5 C4 C3 119.30(15) . . ? 
C6 C5 C4 128.30(15) . . ? 
C6 C5 H5 116.5(16) . . ? 
C4 C5 H5 115.0(16) . . ? 
C5 C6 C7 127.66(15) . . ? 
C5 C6 H6 117.7(14) . . ? 
C7 C6 H6 114.6(14) . . ? 
C6 C7 C1 113.51(14) . . ? 
C6 C7 H7A 107.9(12) . . ? 
C1 C7 H7A 110.2(13) . . ? 
C6 C7 H7B 109.0(13) . . ? 
C1 C7 H7B 108.3(13) . . ? 
H7A C7 H7B 107.9(18) . . ? 
C10 C8 C9 113.18(14) . . ? 
C10 C8 C1 121.05(13) . . ? 
C9 C8 C1 116.00(13) . . ? 
C10 C8 C2 121.46(13) . . ? 
C9 C8 C2 115.46(13) . . ? 
C1 C8 C2 59.81(9) . . ? 
C8 C9 H8D 112.7(13) . . ? 
C8 C9 H8E 109.9(13) . . ? 
H8D C9 H8E 109.7(18) . . ? 
C8 C9 H9C 108.2(16) . . ? 
H8D C9 H9C 109(2) . . ? 
H8E C9 H9C 107.7(19) . . ? 
C8 C10 H8A 114.9(18) . . ? 
C8 C10 H8B 111.3(18) . . ? 
H8A C10 H8B 105(2) . . ? 
C8 C10 H8C 111.1(18) . . ? 
H8A C10 H8C 109(2) . . ? 
H8B C10 H8C 105(2) . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C8 C1 C2 C3 114.74(15) . . . . ? 
C7 C1 C2 C3 1.17(19) . . . . ? 
C7 C1 C2 C8 -113.57(15) . . . . ? 
C1 C2 C3 C4 71.01(17) . . . . ? 
C8 C2 C3 C4 142.23(14) . . . . ? 
C2 C3 C4 O1 112.88(18) . . . . ? 
C2 C3 C4 C5 -66.89(19) . . . . ? 
O1 C4 C5 C6 -169.2(2) . . . . ? 
C3 C4 C5 C6 10.5(3) . . . . ? 
C4 C5 C6 C7 1.8(3) . . . . ? 
C5 C6 C7 C1 46.3(3) . . . . ? 
C2 C1 C7 C6 -63.38(19) . . . . ? 
C8 C1 C7 C6 -134.43(15) . . . . ? 
C2 C1 C8 C10 -110.77(15) . . . . ? 
C7 C1 C8 C10 -4.4(2) . . . . ? 
C2 C1 C8 C9 105.64(14) . . . . ? 
C7 C1 C8 C9 -147.95(14) . . . . ? 
C7 C1 C8 C2 106.40(16) . . . . ? 
C1 C2 C8 C10 110.09(16) . . . . ? 
C3 C2 C8 C10 4.2(2) . . . . ? 
C1 C2 C8 C9 -106.54(15) . . . . ? 
C3 C2 C8 C9 147.60(14) . . . . ? 
C3 C2 C8 C1 -105.86(15) . . . . ? 
  
_refine_diff_density_max    0.185 
_refine_diff_density_min   -0.141 
_refine_diff_density_rms    0.043 
  
  
  
 
data_chai015 
  
_audit_creation_method            'SHELXL-2017/1' 
_shelx_SHELXL_version_number      '2017/1' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
 'C13 H18 O'
_chemical_formula_sum 
 'C13 H18 O' 
_chemical_formula_weight          190.27 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       orthorhombic 
_space_group_IT_number            19 
_space_group_name_H-M_alt         'P 21 21 21' 
_space_group_name_Hall            'P 2ac 2ab' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
  
_cell_length_a                    8.5044(17) 
_cell_length_b                    10.519(2) 
_cell_length_c                    12.5330(17) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      1121.2(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     5680 
_cell_measurement_theta_min       5.49 
_cell_measurement_theta_max       75.39 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.127 
_exptl_crystal_F_000              416 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.346 
_exptl_crystal_size_mid           0.161 
_exptl_crystal_size_min           0.050 
_exptl_absorpt_coefficient_mu     0.530 
_shelx_estimated_absorpt_T_min    0.838 
_shelx_estimated_absorpt_T_max    0.974 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.4361   
_exptl_absorpt_correction_T_max   0.7539 
_exptl_absorpt_process_details    'APEX3 (Bruker, 2015)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       200(2) 
_diffrn_radiation_wavelength      1.54184 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker AXS APEX diffractometer' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.33 
_diffrn_reflns_number             7361 
_diffrn_reflns_av_unetI/netI      0.0618 
_diffrn_reflns_av_R_equivalents   0.0476 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          5.490 
_diffrn_reflns_theta_max          75.284 
_diffrn_reflns_theta_full         67.684 
_diffrn_measured_fraction_theta_max   0.993 
_diffrn_measured_fraction_theta_full  0.999 
_diffrn_reflns_Laue_measured_fraction_max    0.993 
_diffrn_reflns_Laue_measured_fraction_full   0.999 
_diffrn_reflns_point_group_measured_fraction_max   0.986 
_diffrn_reflns_point_group_measured_fraction_full  0.998 
_reflns_number_total              2285 
_reflns_number_gt                 2194 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.704 
_reflns_Friedel_fraction_max      0.976 
_reflns_Friedel_fraction_full     0.996 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.1128P)²] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 866 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    -0.1(3) 
_chemical_absolute_configuration  ad 
_refine_ls_number_reflns          2285 
_refine_ls_number_parameters      129 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0542 
_refine_ls_R_factor_gt            0.0532 
_refine_ls_wR_factor_ref          0.1448 
_refine_ls_wR_factor_gt           0.1432 
_refine_ls_goodness_of_fit_ref    1.016 
_refine_ls_restrained_S_all       1.016 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.7208(2) 0.78866(15) 0.62754(10) 0.0367(4) Uani 1 1 d . . . . . 
C1 C 0.6833(2) 0.87233(19) 0.29949(14) 0.0236(4) Uani 1 1 d . . . . . 
H1 H 0.577732 0.910586 0.285087 0.028 Uiso 1 1 calc R U . . . 
C2 C 0.6806(2) 0.75155(17) 0.36432(12) 0.0192(4) Uani 1 1 d . . . . . 
H2 H 0.572560 0.722858 0.384547 0.023 Uiso 1 1 calc R U . . . 
C3 C 0.8024(2) 0.73165(17) 0.45100(13) 0.0206(4) Uani 1 1 d . . . . . 
H3 H 0.908611 0.751746 0.421270 0.025 Uiso 1 1 calc R U . . . 
C4 C 0.7664(2) 0.82462(18) 0.54045(14) 0.0237(4) Uani 1 1 d . . . . . 
C5 C 0.7872(3) 0.9632(2) 0.52216(15) 0.0298(5) Uani 1 1 d . . . . . 
H5 H 0.785905 1.015044 0.584239 0.036 Uiso 1 1 calc R U . . . 
C6 C 0.8074(3) 1.0240(2) 0.43043(16) 0.0335(5) Uani 1 1 d . . . . . 
H6 H 0.819093 1.113629 0.434857 0.040 Uiso 1 1 calc R U . . . 
C7 C 0.8141(3) 0.9675(2) 0.32006(15) 0.0305(5) Uani 1 1 d . . . . . 
H7A H 0.916805 0.924754 0.310288 0.037 Uiso 1 1 calc R U . . . 
H7B H 0.806921 1.036816 0.266849 0.037 Uiso 1 1 calc R U . . . 
C8 C 0.7132(2) 0.74573(19) 0.24515(14) 0.0225(4) Uani 1 1 d . . . . . 
C9 C 0.5798(3) 0.6928(2) 0.17860(17) 0.0336(5) Uani 1 1 d . . . . . 
H9A H 0.588085 0.725029 0.105464 0.050 Uiso 1 1 calc R U . . . 
H9B H 0.479034 0.719230 0.209413 0.050 Uiso 1 1 calc R U . . . 
H9C H 0.585789 0.599723 0.177857 0.050 Uiso 1 1 calc R U . . . 
C10 C 0.8724(2) 0.7129(2) 0.20063(16) 0.0326(5) Uani 1 1 d . . . . . 
H10A H 0.879852 0.620688 0.190544 0.049 Uiso 1 1 calc R U . . . 
H10B H 0.954189 0.740835 0.250467 0.049 Uiso 1 1 calc R U . . . 
H10C H 0.886861 0.755698 0.131885 0.049 Uiso 1 1 calc R U . . . 
C11 C 0.8030(3) 0.59433(19) 0.49212(15) 0.0301(5) Uani 1 1 d . . . . . 
H11A H 0.879206 0.587281 0.551563 0.036 Uiso 1 1 calc R U . . . 
H11B H 0.697528 0.573516 0.520552 0.036 Uiso 1 1 calc R U . . . 
C12 C 0.8453(3) 0.5000(2) 0.40771(19) 0.0334(5) Uani 1 1 d . . . . . 
H12 H 0.948724 0.503105 0.379233 0.040 Uiso 1 1 calc R U . . . 
C13 C 0.7497(3) 0.4135(2) 0.3704(2) 0.0505(7) Uani 1 1 d . . . . . 
H13A H 0.645385 0.407662 0.397030 0.061 Uiso 1 1 calc R U . . . 
H13B H 0.784539 0.356470 0.316564 0.061 Uiso 1 1 calc R U . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C4 1.219(2) . ? 
C1 C2 1.508(3) . ? 
C1 C8 1.517(3) . ? 
C1 C7 1.519(3) . ? 
C1 H1 1.0000 . ? 
C2 C3 1.515(2) . ? 
C2 C8 1.520(2) . ? 
C2 H2 1.0000 . ? 
C3 C4 1.519(2) . ? 
C3 C11 1.534(3) . ? 
C3 H3 1.0000 . ? 
C4 C5 1.487(3) . ? 
C5 C6 1.326(3) . ? 
C5 H5 0.9500 . ? 
C6 C7 1.506(3) . ? 
C6 H6 0.9500 . ? 
C7 H7A 0.9900 . ? 
C7 H7B 0.9900 . ? 
C8 C10 1.505(2) . ? 
C8 C9 1.515(3) . ? 
C9 H9A 0.9800 . ? 
C9 H9B 0.9800 . ? 
C9 H9C 0.9800 . ? 
C10 H10A 0.9800 . ? 
C10 H10B 0.9800 . ? 
C10 H10C 0.9800 . ? 
C11 C12 1.494(3) . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C12 C13 1.307(3) . ? 
C12 H12 0.9500 . ? 
C13 H13A 0.9500 . ? 
C13 H13B 0.9500 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2 C1 C8 60.33(11) . . ? 
C2 C1 C7 118.34(16) . . ? 
C8 C1 C7 122.12(16) . . ? 
C2 C1 H1 115.0 . . ? 
C8 C1 H1 115.0 . . ? 
C7 C1 H1 115.0 . . ? 
C1 C2 C3 119.50(15) . . ? 
C1 C2 C8 60.13(11) . . ? 
C3 C2 C8 125.05(15) . . ? 
C1 C2 H2 113.9 . . ? 
C3 C2 H2 113.9 . . ? 
C8 C2 H2 113.9 . . ? 
C2 C3 C4 107.61(14) . . ? 
C2 C3 C11 111.94(15) . . ? 
C4 C3 C11 111.05(15) . . ? 
C2 C3 H3 108.7 . . ? 
C4 C3 H3 108.7 . . ? 
C11 C3 H3 108.7 . . ? 
O1 C4 C5 118.72(18) . . ? 
O1 C4 C3 121.69(18) . . ? 
C5 C4 C3 119.59(16) . . ? 
C6 C5 C4 128.43(18) . . ? 
C6 C5 H5 115.8 . . ? 
C4 C5 H5 115.8 . . ? 
C5 C6 C7 127.6(2) . . ? 
C5 C6 H6 116.2 . . ? 
C7 C6 H6 116.2 . . ? 
C6 C7 C1 112.84(17) . . ? 
C6 C7 H7A 109.0 . . ? 
C1 C7 H7A 109.0 . . ? 
C6 C7 H7B 109.0 . . ? 
C1 C7 H7B 109.0 . . ? 
H7A C7 H7B 107.8 . . ? 
C10 C8 C9 112.68(15) . . ? 
C10 C8 C1 121.28(17) . . ? 
C9 C8 C1 116.38(16) . . ? 
C10 C8 C2 122.52(16) . . ? 
C9 C8 C2 114.78(16) . . ? 
C1 C8 C2 59.54(11) . . ? 
C8 C9 H9A 109.5 . . ? 
C8 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
C8 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
C8 C10 H10A 109.5 . . ? 
C8 C10 H10B 109.5 . . ? 
H10A C10 H10B 109.5 . . ? 
C8 C10 H10C 109.5 . . ? 
H10A C10 H10C 109.5 . . ? 
H10B C10 H10C 109.5 . . ? 
C12 C11 C3 112.86(16) . . ? 
C12 C11 H11A 109.0 . . ? 
C3 C11 H11A 109.0 . . ? 
C12 C11 H11B 109.0 . . ? 
C3 C11 H11B 109.0 . . ? 
H11A C11 H11B 107.8 . . ? 
C13 C12 C11 124.5(2) . . ? 
C13 C12 H12 117.7 . . ? 
C11 C12 H12 117.7 . . ? 
C12 C13 H13A 120.0 . . ? 
C12 C13 H13B 120.0 . . ? 
H13A C13 H13B 120.0 . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C8 C1 C2 C3 115.84(17) . . . . ? 
C7 C1 C2 C3 3.0(2) . . . . ? 
C7 C1 C2 C8 -112.83(19) . . . . ? 
C1 C2 C3 C4 69.48(19) . . . . ? 
C8 C2 C3 C4 141.90(18) . . . . ? 
C1 C2 C3 C11 -168.23(15) . . . . ? 
C8 C2 C3 C11 -95.8(2) . . . . ? 
C2 C3 C4 O1 112.4(2) . . . . ? 
C11 C3 C4 O1 -10.5(3) . . . . ? 
C2 C3 C4 C5 -67.7(2) . . . . ? 
C11 C3 C4 C5 169.42(17) . . . . ? 
O1 C4 C5 C6 -166.6(2) . . . . ? 
C3 C4 C5 C6 13.5(3) . . . . ? 
C4 C5 C6 C7 0.2(4) . . . . ? 
C5 C6 C7 C1 46.5(3) . . . . ? 
C2 C1 C7 C6 -64.6(2) . . . . ? 
C8 C1 C7 C6 -135.65(19) . . . . ? 
C2 C1 C8 C10 -111.87(19) . . . . ? 
C7 C1 C8 C10 -5.2(3) . . . . ? 
C2 C1 C8 C9 104.55(19) . . . . ? 
C7 C1 C8 C9 -148.75(18) . . . . ? 
C7 C1 C8 C2 106.70(19) . . . . ? 
C1 C2 C8 C10 109.8(2) . . . . ? 
C3 C2 C8 C10 2.9(3) . . . . ? 
C1 C2 C8 C9 -107.23(19) . . . . ? 
C3 C2 C8 C9 145.86(18) . . . . ? 
C3 C2 C8 C1 -106.9(2) . . . . ? 
C2 C3 C11 C12 62.3(2) . . . . ? 
C4 C3 C11 C12 -177.36(17) . . . . ? 
C3 C11 C12 C13 -114.3(3) . . . . ? 
  
_refine_diff_density_max    0.247 
_refine_diff_density_min   -0.291 
_refine_diff_density_rms    0.050 
  
  
  
 
data_chai048 
  
_audit_creation_method            'SHELXL-2017/1' 
_shelx_SHELXL_version_number      '2017/1' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety 
 'C29 H33 Br O3' 
_chemical_formula_sum 
 'C29 H33 Br O3' 
_chemical_formula_weight          509.46 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Br'  'Br'  -0.6763   1.2805 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       orthorhombic 
_space_group_IT_number            19 
_space_group_name_H-M_alt         'P 21 21 21' 
_space_group_name_Hall            'P 2ac 2ab' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
  
_cell_length_a                    9.4837(3) 
_cell_length_b                    10.0331(3) 
_cell_length_c                    26.2857(9) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      2501.11(14) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     9326 
_cell_measurement_theta_min       4.72 
_cell_measurement_theta_max       75.44 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.353 
_exptl_crystal_F_000              1064 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.472 
_exptl_crystal_size_mid           0.357 
_exptl_crystal_size_min           0.096 
_exptl_absorpt_coefficient_mu     2.453 
_shelx_estimated_absorpt_T_min    0.391 
_shelx_estimated_absorpt_T_max    0.799 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.4362 
_exptl_absorpt_correction_T_max   0.7539 
_exptl_absorpt_process_details 
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       200(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker AXS APEX diffractometer' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.33 
_diffrn_reflns_number             36748 
_diffrn_reflns_av_unetI/netI      0.0420 
_diffrn_reflns_av_R_equivalents   0.0729 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -32 
_diffrn_reflns_limit_l_max        31 
_diffrn_reflns_theta_min          3.363 
_diffrn_reflns_theta_max          75.595 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.998 
_diffrn_measured_fraction_theta_full  1.000 
_diffrn_reflns_Laue_measured_fraction_max    0.998 
_diffrn_reflns_Laue_measured_fraction_full   1.000 
_diffrn_reflns_point_group_measured_fraction_max   0.995 
_diffrn_reflns_point_group_measured_fraction_full  0.999 
_reflns_number_total              5164 
_reflns_number_gt                 5025 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.751 
_reflns_Friedel_fraction_max      0.992 
_reflns_Friedel_fraction_full     0.998 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0601P)²+0.1851P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      'SHELXL-2017/1 (Sheldrick 2017)' 
_refine_ls_extinction_coef        0.0022(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2101 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    -0.003(8) 
_chemical_absolute_configuration  rm
_refine_ls_number_reflns          5164 
_refine_ls_number_parameters      306 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0361 
_refine_ls_R_factor_gt            0.0354 
_refine_ls_wR_factor_ref          0.0948 
_refine_ls_wR_factor_gt           0.0939 
_refine_ls_goodness_of_fit_ref    1.092 
_refine_ls_restrained_S_all       1.092 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Br1 Br -0.01706(3) 0.49256(3) 0.60535(2) 0.04831(14) Uani 1 1 d . . . . . 
O1 O 0.5666(3) 0.5063(2) 0.70424(10) 0.0565(6) Uani 1 1 d . . . . . 
O2 O 0.0064(3) 0.0613(2) 0.70601(9) 0.0546(6) Uani 1 1 d . . . . . 
O3 O 0.4471(2) 0.2797(2) 0.68630(10) 0.0482(5) Uani 1 1 d . . . . . 
H3 H 0.4755(19) 0.355(4) 0.6908(18) 0.072 Uiso 1 1 calc R U . . . 
C1 C 0.5231(4) 0.6039(3) 0.68046(11) 0.0422(7) Uani 1 1 d . . . . . 
C2 C 0.5944(4) 0.7303(3) 0.67579(13) 0.0457(7) Uani 1 1 d . . . . . 
H2 H 0.680607 0.752059 0.692181 0.055 Uiso 1 1 calc R U . . . 
C3 C 0.5222(3) 0.8133(3) 0.64508(10) 0.0345(5) Uani 1 1 d . . . . . 
C4 C 0.5486(4) 0.9600(3) 0.63707(12) 0.0377(6) Uani 1 1 d . . . . . 
H4 H 0.469626 1.007451 0.654653 0.045 Uiso 1 1 calc R U . . . 
C5 C 0.6838(4) 1.0077(4) 0.66272(15) 0.0556(8) Uani 1 1 d . . . . . 
H5A H 0.765438 0.969441 0.645167 0.083 Uiso 1 1 calc R U . . . 
H5B H 0.684067 0.979216 0.698373 0.083 Uiso 1 1 calc R U . . . 
H5C H 0.688650 1.105219 0.661079 0.083 Uiso 1 1 calc R U . . . 
C6 C 0.5458(3) 1.0084(3) 0.58151(12) 0.0440(6) Uani 1 1 d . . . . . 
H6A H 0.546925 1.107081 0.581653 0.053 Uiso 1 1 calc R U . . . 
H6B H 0.633715 0.978310 0.564764 0.053 Uiso 1 1 calc R U . . . 
C7 C 0.4207(3) 0.9624(3) 0.54893(12) 0.0398(7) Uani 1 1 d . . . . . 
H7A H 0.406691 1.026881 0.520878 0.048 Uiso 1 1 calc R U . . . 
H7B H 0.443890 0.875053 0.533533 0.048 Uiso 1 1 calc R U . . . 
C8 C 0.2846(3) 0.9494(3) 0.57823(11) 0.0357(6) Uani 1 1 d . . . . . 
H8 H 0.243327 1.035314 0.590446 0.043 Uiso 1 1 calc R U . . . 
C9 C 0.1788(3) 0.8400(3) 0.56781(11) 0.0376(6) Uani 1 1 d . . . . . 
C10 C 0.2706(3) 0.8325(2) 0.61509(10) 0.0319(5) Uani 1 1 d . . . . . 
H10 H 0.220324 0.854506 0.647472 0.038 Uiso 1 1 calc R U . . . 
C11 C 0.1995(4) 0.7473(3) 0.52325(12) 0.0461(7) Uani 1 1 d . . . . . 
H11A H 0.175634 0.794009 0.491655 0.069 Uiso 1 1 calc R U . . . 
H11B H 0.138107 0.669362 0.527148 0.069 Uiso 1 1 calc R U . . . 
H11C H 0.298078 0.718294 0.521984 0.069 Uiso 1 1 calc R U . . . 
C12 C 0.0250(4) 0.8719(3) 0.57779(15) 0.0532(8) Uani 1 1 d . . . . . 
H12A H -0.017571 0.908908 0.546895 0.080 Uiso 1 1 calc R U . . . 
H12B H 0.018185 0.937233 0.605404 0.080 Uiso 1 1 calc R U . . . 
H12C H -0.024923 0.790310 0.587520 0.080 Uiso 1 1 calc R U . . . 
C13 C 0.3961(3) 0.7426(2) 0.62161(9) 0.0295(5) Uani 1 1 d . . . . . 
H13 H 0.425037 0.712309 0.586908 0.035 Uiso 1 1 calc R U . . . 
C14 C 0.3774(3) 0.6148(3) 0.65522(10) 0.0331(5) Uani 1 1 d . . . . . 
C15 C 0.2745(4) 0.6406(3) 0.69956(11) 0.0422(7) Uani 1 1 d . . . . . 
H15A H 0.178900 0.652292 0.686134 0.063 Uiso 1 1 calc R U . . . 
H15B H 0.303112 0.721469 0.717774 0.063 Uiso 1 1 calc R U . . . 
H15C H 0.276135 0.564601 0.722953 0.063 Uiso 1 1 calc R U . . . 
C16 C 0.3191(3) 0.4984(2) 0.62190(10) 0.0300(5) Uani 1 1 d . . . . . 
H16 H 0.242007 0.542902 0.602309 0.036 Uiso 1 1 calc R U . . . 
C17 C 0.5600(3) 0.4389(3) 0.58064(14) 0.0435(7) Uani 1 1 d . . . . . 
H17 H 0.609140 0.470629 0.609705 0.052 Uiso 1 1 calc R U . . . 
C18 C 0.6352(4) 0.3880(3) 0.53967(16) 0.0526(8) Uani 1 1 d . . . . . 
H18 H 0.735327 0.386601 0.540832 0.063 Uiso 1 1 calc R U . . . 
C19 C 0.5666(4) 0.3396(3) 0.49746(14) 0.0493(8) Uani 1 1 d . . . . . 
H19 H 0.618742 0.303166 0.469900 0.059 Uiso 1 1 calc R U . . . 
C20 C 0.4213(4) 0.3443(3) 0.49551(13) 0.0485(8) Uani 1 1 d . . . . . 
H20 H 0.372920 0.311925 0.466379 0.058 Uiso 1 1 calc R U . . . 
C21 C 0.3458(4) 0.3965(3) 0.53613(12) 0.0424(7) Uani 1 1 d . . . . . 
H21 H 0.245778 0.399916 0.534323 0.051 Uiso 1 1 calc R U . . . 
C22 C 0.4138(3) 0.4441(2) 0.57958(11) 0.0318(6) Uani 1 1 d . . . . . 
C23 C 0.0947(3) 0.3649(3) 0.64130(10) 0.0341(6) Uani 1 1 d . . . . . 
C24 C 0.0191(3) 0.2582(3) 0.65974(10) 0.0381(6) Uani 1 1 d . . . . . 
H24 H -0.078950 0.250341 0.653051 0.046 Uiso 1 1 calc R U . . . 
C25 C 0.0890(4) 0.1622(3) 0.68830(11) 0.0376(6) Uani 1 1 d . . . . . 
C26 C 0.2321(3) 0.1746(3) 0.69715(10) 0.0361(6) Uani 1 1 d . . . . . 
H26 H 0.279846 0.109507 0.716976 0.043 Uiso 1 1 calc R U . . . 
C27 C 0.3068(3) 0.2823(3) 0.67707(11) 0.0353(6) Uani 1 1 d . . . . . 
C28 C 0.2410(3) 0.3834(3) 0.64814(10) 0.0313(5) Uani 1 1 d . . . . . 
C29 C 0.0644(5) -0.0272(3) 0.74244(14) 0.0554(9) Uani 1 1 d . . . . . 
H29A H -0.007278 -0.092350 0.752616 0.083 Uiso 1 1 calc R U . . . 
H29B H 0.095253 0.023324 0.772335 0.083 Uiso 1 1 calc R U . . . 
H29C H 0.145276 -0.073884 0.727566 0.083 Uiso 1 1 calc R U . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Br1 C23 1.912(3) . ? 
O1 C1 1.233(4) . ? 
O2 C25 1.361(3) . ? 
O2 C29 1.417(4) . ? 
O3 C27 1.352(4) . ? 
O3 H3 0.81(5) . ? 
C1 C2 1.442(4) . ? 
C1 C14 1.537(4) . ? 
C2 C3 1.347(4) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.508(3) . ? 
C3 C13 1.521(4) . ? 
C4 C5 1.526(4) . ? 
C4 C6 1.539(5) . ? 
C4 H4 1.0000 . ? 
C5 H5A 0.9800 . ? 
C5 H5B 0.9800 . ? 
C5 H5C 0.9800 . ? 
C6 C7 1.535(4) . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
C7 C8 1.508(4) . ? 
C7 H7A 0.9900 . ? 
C7 H7B 0.9900 . ? 
C8 C9 1.512(4) . ? 
C8 C10 1.527(3) . ? 
C8 H8 1.0000 . ? 
C9 C11 1.508(4) . ? 
C9 C12 1.516(4) . ? 
C9 C10 1.519(4) . ? 
C10 C13 1.503(4) . ? 
C10 H10 1.0000 . ? 
C11 H11A 0.9800 . ? 
C11 H11B 0.9800 . ? 
C11 H11C 0.9800 . ? 
C12 H12A 0.9800 . ? 
C12 H12B 0.9800 . ? 
C12 H12C 0.9800 . ? 
C13 C14 1.568(3) . ? 
C13 H13 1.0000 . ? 
C14 C15 1.542(4) . ? 
C14 C16 1.561(3) . ? 
C15 H15A 0.9800 . ? 
C15 H15B 0.9800 . ? 
C15 H15C 0.9800 . ? 
C16 C22 1.530(4) . ? 
C16 C28 1.535(3) . ? 
C16 H16 1.0000 . ? 
C17 C22 1.387(4) . ? 
C17 C18 1.389(5) . ? 
C17 H17 0.9500 . ? 
C18 C19 1.375(6) . ? 
C18 H18 0.9500 . ? 
C19 C20 1.380(5) . ? 
C19 H19 0.9500 . ? 
C20 C21 1.388(5) . ? 
C20 H20 0.9500 . ? 
C21 C22 1.396(4) . ? 
C21 H21 0.9500 . ? 
C23 C24 1.376(4) . ? 
C23 C28 1.411(4) . ? 
C24 C25 1.389(4) . ? 
C24 H24 0.9500 . ? 
C25 C26 1.383(5) . ? 
C26 C27 1.396(4) . ? 
C26 H26 0.9500 . ? 
C27 C28 1.413(4) . ? 
C29 H29A 0.9800 . ? 
C29 H29B 0.9800 . ? 
C29 H29C 0.9800 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C25 O2 C29 118.3(3) . . ? 
C27 O3 H3 109.5 . . ? 
O1 C1 C2 125.8(3) . . ? 
O1 C1 C14 125.2(3) . . ? 
C2 C1 C14 108.8(2) . . ? 
C3 C2 C1 110.9(3) . . ? 
C3 C2 H2 124.5 . . ? 
C1 C2 H2 124.5 . . ? 
C2 C3 C4 127.1(3) . . ? 
C2 C3 C13 110.7(2) . . ? 
C4 C3 C13 121.9(2) . . ? 
C3 C4 C5 112.6(3) . . ? 
C3 C4 C6 115.9(2) . . ? 
C5 C4 C6 109.5(3) . . ? 
C3 C4 H4 106.0 . . ? 
C5 C4 H4 106.0 . . ? 
C6 C4 H4 106.0 . . ? 
C4 C5 H5A 109.5 . . ? 
C4 C5 H5B 109.5 . . ? 
H5A C5 H5B 109.5 . . ? 
C4 C5 H5C 109.5 . . ? 
H5A C5 H5C 109.5 . . ? 
H5B C5 H5C 109.5 . . ? 
C7 C6 C4 116.6(2) . . ? 
C7 C6 H6A 108.1 . . ? 
C4 C6 H6A 108.1 . . ? 
C7 C6 H6B 108.1 . . ? 
C4 C6 H6B 108.1 . . ? 
H6A C6 H6B 107.3 . . ? 
C8 C7 C6 113.7(3) . . ? 
C8 C7 H7A 108.8 . . ? 
C6 C7 H7A 108.8 . . ? 
C8 C7 H7B 108.8 . . ? 
C6 C7 H7B 108.8 . . ? 
H7A C7 H7B 107.7 . . ? 
C7 C8 C9 122.6(3) . . ? 
C7 C8 C10 117.7(2) . . ? 
C9 C8 C10 59.98(18) . . ? 
C7 C8 H8 115.1 . . ? 
C9 C8 H8 115.1 . . ? 
C10 C8 H8 115.1 . . ? 
C11 C9 C8 120.1(3) . . ? 
C11 C9 C12 112.9(3) . . ? 
C8 C9 C12 117.0(3) . . ? 
C11 C9 C10 122.1(2) . . ? 
C8 C9 C10 60.47(18) . . ? 
C12 C9 C10 114.8(3) . . ? 
C13 C10 C9 125.2(2) . . ? 
C13 C10 C8 117.6(2) . . ? 
C9 C10 C8 59.55(18) . . ? 
C13 C10 H10 114.4 . . ? 
C9 C10 H10 114.4 . . ? 
C8 C10 H10 114.4 . . ? 
C9 C11 H11A 109.5 . . ? 
C9 C11 H11B 109.5 . . ? 
H11A C11 H11B 109.5 . . ? 
C9 C11 H11C 109.5 . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
C9 C12 H12A 109.5 . . ? 
C9 C12 H12B 109.5 . . ? 
H12A C12 H12B 109.5 . . ? 
C9 C12 H12C 109.5 . . ? 
H12A C12 H12C 109.5 . . ? 
H12B C12 H12C 109.5 . . ? 
C10 C13 C3 112.9(2) . . ? 
C10 C13 C14 117.7(2) . . ? 
C3 C13 C14 104.0(2) . . ? 
C10 C13 H13 107.2 . . ? 
C3 C13 H13 107.2 . . ? 
C14 C13 H13 107.2 . . ? 
C1 C14 C15 104.8(2) . . ? 
C1 C14 C16 120.5(2) . . ? 
C15 C14 C16 109.0(2) . . ? 
C1 C14 C13 101.5(2) . . ? 
C15 C14 C13 111.1(2) . . ? 
C16 C14 C13 109.6(2) . . ? 
C14 C15 H15A 109.5 . . ? 
C14 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C14 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 109.5 . . ? 
C22 C16 C28 110.0(2) . . ? 
C22 C16 C14 117.8(2) . . ? 
C28 C16 C14 118.8(2) . . ? 
C22 C16 H16 102.3 . . ? 
C28 C16 H16 102.3 . . ? 
C14 C16 H16 102.3 . . ? 
C22 C17 C18 120.8(3) . . ? 
C22 C17 H17 119.6 . . ? 
C18 C17 H17 119.6 . . ? 
C19 C18 C17 120.8(3) . . ? 
C19 C18 H18 119.6 . . ? 
C17 C18 H18 119.6 . . ? 
C18 C19 C20 119.4(3) . . ? 
C18 C19 H19 120.3 . . ? 
C20 C19 H19 120.3 . . ? 
C19 C20 C21 120.0(4) . . ? 
C19 C20 H20 120.0 . . ? 
C21 C20 H20 120.0 . . ? 
C20 C21 C22 121.3(3) . . ? 
C20 C21 H21 119.3 . . ? 
C22 C21 H21 119.3 . . ? 
C17 C22 C21 117.7(3) . . ? 
C17 C22 C16 125.8(3) . . ? 
C21 C22 C16 116.5(3) . . ? 
C24 C23 C28 124.7(3) . . ? 
C24 C23 Br1 114.0(2) . . ? 
C28 C23 Br1 121.3(2) . . ? 
C23 C24 C25 118.8(3) . . ? 
C23 C24 H24 120.6 . . ? 
C25 C24 H24 120.6 . . ? 
O2 C25 C26 125.0(3) . . ? 
O2 C25 C24 115.2(3) . . ? 
C26 C25 C24 119.8(3) . . ? 
C25 C26 C27 120.3(3) . . ? 
C25 C26 H26 119.9 . . ? 
C27 C26 H26 119.9 . . ? 
O3 C27 C26 114.6(3) . . ? 
O3 C27 C28 123.0(3) . . ? 
C26 C27 C28 122.4(3) . . ? 
C23 C28 C27 114.1(3) . . ? 
C23 C28 C16 121.1(2) . . ? 
C27 C28 C16 124.6(2) . . ? 
O2 C29 H29A 109.5 . . ? 
O2 C29 H29B 109.5 . . ? 
H29A C29 H29B 109.5 . . ? 
O2 C29 H29C 109.5 . . ? 
H29A C29 H29C 109.5 . . ? 
H29B C29 H29C 109.5 . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
O1 C1 C2 C3 176.8(3) . . . . ? 
C14 C1 C2 C3 -8.6(4) . . . . ? 
C1 C2 C3 C4 169.6(3) . . . . ? 
C1 C2 C3 C13 -5.0(4) . . . . ? 
C2 C3 C4 C5 7.9(5) . . . . ? 
C13 C3 C4 C5 -178.0(3) . . . . ? 
C2 C3 C4 C6 135.2(3) . . . . ? 
C13 C3 C4 C6 -50.8(4) . . . . ? 
C3 C4 C6 C7 47.8(4) . . . . ? 
C5 C4 C6 C7 176.6(3) . . . . ? 
C4 C6 C7 C8 34.1(4) . . . . ? 
C6 C7 C8 C9 -143.0(3) . . . . ? 
C6 C7 C8 C10 -72.6(3) . . . . ? 
C7 C8 C9 C11 -6.5(4) . . . . ? 
C10 C8 C9 C11 -112.1(3) . . . . ? 
C7 C8 C9 C12 -149.7(3) . . . . ? 
C10 C8 C9 C12 104.7(3) . . . . ? 
C7 C8 C9 C10 105.6(3) . . . . ? 
C11 C9 C10 C13 4.9(4) . . . . ? 
C8 C9 C10 C13 -104.1(3) . . . . ? 
C12 C9 C10 C13 147.7(3) . . . . ? 
C11 C9 C10 C8 109.0(3) . . . . ? 
C12 C9 C10 C8 -108.2(3) . . . . ? 
C7 C8 C10 C13 3.1(4) . . . . ? 
C9 C8 C10 C13 116.5(3) . . . . ? 
C7 C8 C10 C9 -113.5(3) . . . . ? 
C9 C10 C13 C3 135.3(3) . . . . ? 
C8 C10 C13 C3 64.6(3) . . . . ? 
C9 C10 C13 C14 -103.4(3) . . . . ? 
C8 C10 C13 C14 -174.1(2) . . . . ? 
C2 C3 C13 C10 144.8(3) . . . . ? 
C4 C3 C13 C10 -30.1(4) . . . . ? 
C2 C3 C13 C14 16.0(3) . . . . ? 
C4 C3 C13 C14 -158.9(3) . . . . ? 
O1 C1 C14 C15 76.5(4) . . . . ? 
C2 C1 C14 C15 -98.2(3) . . . . ? 
O1 C1 C14 C16 -46.6(4) . . . . ? 
C2 C1 C14 C16 138.7(3) . . . . ? 
O1 C1 C14 C13 -167.8(3) . . . . ? 
C2 C1 C14 C13 17.5(3) . . . . ? 
C10 C13 C14 C1 -145.1(2) . . . . ? 
C3 C13 C14 C1 -19.3(3) . . . . ? 
C10 C13 C14 C15 -34.1(3) . . . . ? 
C3 C13 C14 C15 91.6(3) . . . . ? 
C10 C13 C14 C16 86.4(3) . . . . ? 
C3 C13 C14 C16 -147.8(2) . . . . ? 
C1 C14 C16 C22 -51.4(3) . . . . ? 
C15 C14 C16 C22 -172.4(2) . . . . ? 
C13 C14 C16 C22 65.8(3) . . . . ? 
C1 C14 C16 C28 85.7(3) . . . . ? 
C15 C14 C16 C28 -35.4(3) . . . . ? 
C13 C14 C16 C28 -157.2(2) . . . . ? 
C22 C17 C18 C19 -1.0(5) . . . . ? 
C17 C18 C19 C20 1.3(5) . . . . ? 
C18 C19 C20 C21 -0.6(5) . . . . ? 
C19 C20 C21 C22 -0.4(5) . . . . ? 
C18 C17 C22 C21 0.0(5) . . . . ? 
C18 C17 C22 C16 -179.6(3) . . . . ? 
C20 C21 C22 C17 0.7(4) . . . . ? 
C20 C21 C22 C16 -179.6(3) . . . . ? 
C28 C16 C22 C17 -108.8(3) . . . . ? 
C14 C16 C22 C17 31.7(4) . . . . ? 
C28 C16 C22 C21 71.6(3) . . . . ? 
C14 C16 C22 C21 -147.9(2) . . . . ? 
C28 C23 C24 C25 1.7(4) . . . . ? 
Br1 C23 C24 C25 -177.4(2) . . . . ? 
C29 O2 C25 C26 10.1(5) . . . . ? 
C29 O2 C25 C24 -169.3(3) . . . . ? 
C23 C24 C25 O2 178.7(3) . . . . ? 
C23 C24 C25 C26 -0.7(4) . . . . ? 
O2 C25 C26 C27 180.0(3) . . . . ? 
C24 C25 C26 C27 -0.7(4) . . . . ? 
C25 C26 C27 O3 -176.9(3) . . . . ? 
C25 C26 C27 C28 1.2(4) . . . . ? 
C24 C23 C28 C27 -1.1(4) . . . . ? 
Br1 C23 C28 C27 177.86(19) . . . . ? 
C24 C23 C28 C16 174.0(3) . . . . ? 
Br1 C23 C28 C16 -7.0(4) . . . . ? 
O3 C27 C28 C23 177.6(3) . . . . ? 
C26 C27 C28 C23 -0.4(4) . . . . ? 
O3 C27 C28 C16 2.7(4) . . . . ? 
C26 C27 C28 C16 -175.3(3) . . . . ? 
C22 C16 C28 C23 -108.9(3) . . . . ? 
C14 C16 C28 C23 111.0(3) . . . . ? 
C22 C16 C28 C27 65.7(3) . . . . ? 
C14 C16 C28 C27 -74.4(3) . . . . ? 
  
_refine_diff_density_max    0.553 
_refine_diff_density_min   -0.587 
_refine_diff_density_rms    0.074 
  
  
  
data_chai064
_audit_creation_date               2023-06-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number       '2019/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C30 H35 Br O3'
_chemical_formula_sum              'C30 H35 Br O3'
_chemical_formula_weight           523.49
_chemical_absolute_configuration   ad
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br' 'Br' -0.6763 1.2805
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             1
_space_group_name_H-M_alt          'P 1'
_space_group_name_Hall             'P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'

_cell_length_a                     8.7028(8)
_cell_length_b                     9.7695(9)
_cell_length_c                     16.5089(15)
_cell_angle_alpha                  87.368(3)
_cell_angle_beta                   79.910(3)
_cell_angle_gamma                  70.699(3)
_cell_volume                       1304.1(2)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      9732
_cell_measurement_temperature      100.00
_cell_measurement_theta_max        69.950
_cell_measurement_theta_min        4.796
_shelx_estimated_absorpt_T_max     0.841
_shelx_estimated_absorpt_T_min     0.713
_exptl_absorpt_coefficient_mu      2.367
_exptl_absorpt_correction_T_max    0.7533
_exptl_absorpt_correction_T_min    0.5740
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1362 before and 0.0746 after correction.
The Ratio of minimum to maximum transmission is 0.7620.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.333
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               548
_exptl_crystal_recrystallization_method  'slow evaporation from ether solution'
_exptl_crystal_size_max            0.153
_exptl_crystal_size_mid            0.079
_exptl_crystal_size_min            0.076
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0380
_diffrn_reflns_av_unetI/netI       0.0268
_diffrn_reflns_Laue_measured_fraction_full  0.994
_diffrn_reflns_Laue_measured_fraction_max  0.994
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -11
_diffrn_reflns_limit_l_max         19
_diffrn_reflns_limit_l_min         -19
_diffrn_reflns_number              46954
_diffrn_reflns_point_group_measured_fraction_full  0.959
_diffrn_reflns_point_group_measured_fraction_max  0.959
_diffrn_reflns_theta_full          67.494
_diffrn_reflns_theta_max           67.494
_diffrn_reflns_theta_min           4.796
_diffrn_ambient_temperature        100.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.994
_diffrn_measured_fraction_theta_max  0.994
_diffrn_measurement_device_type    'Bruker Venture Photon III'
_diffrn_measurement_method         ?
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     ?
_diffrn_source_current             1.2
_diffrn_source_power               0.06
_diffrn_source_voltage             50.0
_reflns_Friedel_coverage           0.928
_reflns_Friedel_fraction_full      0.923
_reflns_Friedel_fraction_max       0.923
_reflns_number_gt                  9016
_reflns_number_total               9040
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           1.608
_refine_diff_density_min           -0.842
_refine_diff_density_rms           0.107
_refine_ls_abs_structure_details
;
 Flack x determined using 4271 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.018(17)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.096
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       625
_refine_ls_number_reflns           9040
_refine_ls_number_restraints       3
_refine_ls_R_factor_all            0.0568
_refine_ls_R_factor_gt             0.0567
_refine_ls_restrained_S_all        1.096
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0254P)²+9.1106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1431
_refine_ls_wR_factor_ref           0.1432
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C22(H22), C25(H25), C26(H26), C27(H27), C40(H40), C51(H51), C53(H53),
 C56(H56), C57(H57)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C54(H54A,H54B), C55(H55A,H55B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18),
 C33(H33), C35(H35), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C49(H49)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C),
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C), C52(H52A,H52B,H52C), C58(H58A,H58B,H58C), C60(H60A,H60B,H60C), C61(H61A,
 H61B,H61C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Br1 Br 0.69912(8) 0.68934(7) -0.00789(5) 0.0198(2) Uani 1 1 d . . . . .
 O1 O 1.1881(8) 0.3457(7) 0.1237(4) 0.0207(14) Uani 1 1 d . . . . .
 O2 O 0.7293(8) 0.6394(7) 0.3076(4) 0.0208(13) Uani 1 1 d . . . . .
 O3 O 0.5013(8) 0.5014(7) 0.3091(4) 0.0266(15) Uani 1 1 d . . . . .
 C1 C 0.7980(11) 0.6110(10) 0.0879(5) 0.0190(18) Uani 1 1 d . . . . .
 C2 C 0.9571(11) 0.5119(10) 0.0681(6) 0.0181(18) Uani 1 1 d . . . . .
 H2 H 1.009913 0.490206 0.012544 0.022 Uiso 1 1 calc R U . . .
 C3 C 1.0334(10) 0.4475(9) 0.1323(5) 0.0143(16) Uani 1 1 d . . . . .
 C4 C 0.9589(11) 0.4858(10) 0.2134(5) 0.0188(18) Uani 1 1 d . . . . .
 H4 H 1.014158 0.441062 0.257384 0.023 Uiso 1 1 calc R U . . .
 C5 C 0.8025(11) 0.5905(9) 0.2299(5) 0.0165(18) Uani 1 1 d . . . . .
 C6 C 0.7147(10) 0.6527(9) 0.1663(5) 0.0144(17) Uani 1 1 d . . . . .
 C7 C 1.2879(11) 0.3280(10) 0.0434(6) 0.0200(19) Uani 1 1 d . . . . .
 H7A H 1.234026 0.294794 0.004571 0.030 Uiso 1 1 calc R U . . .
 H7B H 1.396633 0.256127 0.045533 0.030 Uiso 1 1 calc R U . . .
 H7C H 1.301055 0.421007 0.025246 0.030 Uiso 1 1 calc R U . . .
 C8 C 0.7891(12) 0.5515(12) 0.3742(6) 0.028(2) Uani 1 1 d . . . . .
 H8A H 0.782955 0.454253 0.368181 0.043 Uiso 1 1 calc R U . . .
 H8B H 0.721372 0.595302 0.426345 0.043 Uiso 1 1 calc R U . . .
 H8C H 0.904146 0.544713 0.373901 0.043 Uiso 1 1 calc R U . . .
 C9 C 0.5367(11) 0.7604(9) 0.1838(5) 0.0168(17) Uani 1 1 d . . . . .
 H9 H 0.516229 0.798173 0.127939 0.020 Uiso 1 1 calc R U . . .
 C10 C 0.4715(11) 0.9134(10) 0.3177(6) 0.0217(19) Uani 1 1 d . . . . .
 H10 H 0.463362 0.832564 0.350274 0.026 Uiso 1 1 calc R U . . .
 C11 C 0.4390(12) 1.0484(11) 0.3561(6) 0.027(2) Uani 1 1 d . . . . .
 H11 H 0.404221 1.058831 0.414017 0.032 Uiso 1 1 calc R U . . .
 C12 C 0.4576(12) 1.1670(11) 0.3097(6) 0.029(2) Uani 1 1 d . . . . .
 H12 H 0.438731 1.257388 0.335602 0.034 Uiso 1 1 calc R U . . .
 C13 C 0.5045(13) 1.1497(11) 0.2248(7) 0.028(2) Uani 1 1 d . . . . .
 H13 H 0.517260 1.229155 0.192172 0.034 Uiso 1 1 calc R U . . .
 C14 C 0.5324(12) 1.0182(10) 0.1876(6) 0.0218(19) Uani 1 1 d . . . . .
 H14 H 0.564306 1.009473 0.129560 0.026 Uiso 1 1 calc R U . . .
 C15 C 0.5157(10) 0.8973(9) 0.2319(5) 0.0162(17) Uani 1 1 d . . . . .
 C16 C 0.3978(10) 0.6889(9) 0.2118(5) 0.0163(17) Uani 1 1 d . . . . .
 C17 C 0.3950(11) 0.6127(10) 0.2948(5) 0.0191(19) Uani 1 1 d . . . . .
 C18 C 0.2353(12) 0.6836(11) 0.3461(6) 0.023(2) Uani 1 1 d . . . . .
 H18 H 0.204948 0.657667 0.401292 0.028 Uiso 1 1 calc R U . . .
 C19 C 0.1379(11) 0.7885(10) 0.3063(5) 0.0187(18) Uani 1 1 d . . . . .
 C21 C 0.4172(11) 0.5723(10) 0.1477(6) 0.0204(19) Uani 1 1 d . . . . .
 H21A H 0.526662 0.498581 0.144314 0.031 Uiso 1 1 calc R U . . .
 H21B H 0.405519 0.617371 0.093895 0.031 Uiso 1 1 calc R U . . .
 H21C H 0.331922 0.526696 0.164165 0.031 Uiso 1 1 calc R U . . .
 C22 C -0.0413(12) 0.8765(11) 0.3326(6) 0.026(2) Uani 1 1 d . . . . .
 H22 H -0.107317 0.834281 0.303622 0.031 Uiso 1 1 calc R U . . .
 C23 C -0.0840(13) 1.0379(11) 0.3088(6) 0.029(2) Uani 1 1 d . . . . .
 H23A H -0.020883 1.081527 0.337917 0.035 Uiso 1 1 calc R U . . .
 H23B H -0.202690 1.087012 0.329927 0.035 Uiso 1 1 calc R U . . .
 C24 C -0.0505(14) 1.0734(13) 0.2154(7) 0.028(3) Uani 1 1 d . . . . .
 H24A H -0.143220 1.158794 0.203612 0.033 Uiso 1 1 calc R U . . .
 H24B H 0.050825 1.100950 0.204392 0.033 Uiso 1 1 calc R U . . .
 C25 C -0.0301(11) 0.9529(10) 0.1565(6) 0.0213(19) Uani 1 1 d . . . . .
 H25 H -0.135077 0.938156 0.148883 0.026 Uiso 1 1 calc R U . . .
 C26 C 0.1153(10) 0.8147(9) 0.1590(6) 0.0159(18) Uani 1 1 d . . . . .
 H26 H 0.091268 0.722859 0.152753 0.019 Uiso 1 1 calc R U . . .
 C27 C 0.2242(10) 0.8098(10) 0.2210(5) 0.0165(18) Uani 1 1 d . . . . .
 H27 H 0.241950 0.905853 0.220733 0.020 Uiso 1 1 calc R U . . .
 C28 C -0.0984(14) 0.8653(13) 0.4252(6) 0.035(3) Uani 1 1 d . . . . .
 H28A H -0.074631 0.763052 0.440081 0.053 Uiso 1 1 calc R U . . .
 H28B H -0.217523 0.916213 0.438978 0.053 Uiso 1 1 calc R U . . .
 H28C H -0.039608 0.909647 0.455746 0.053 Uiso 1 1 calc R U . . .
 C29 C 0.1109(11) 0.9090(10) 0.0822(5) 0.0192(18) Uani 1 1 d . . . . .
 C30 C 0.0743(12) 0.8499(10) 0.0069(6) 0.024(2) Uani 1 1 d . . . . .
 H30A H 0.011418 0.783780 0.024329 0.035 Uiso 1 1 calc R U . . .
 H30B H 0.178398 0.797275 -0.028464 0.035 Uiso 1 1 calc R U . . .
 H30C H 0.009545 0.930334 -0.023589 0.035 Uiso 1 1 calc R U . . .
 C31 C 0.2254(12) 0.9961(10) 0.0604(6) 0.0220(19) Uani 1 1 d . . . . .
 H31A H 0.175027 1.078922 0.026990 0.033 Uiso 1 1 calc R U . . .
 H31B H 0.330351 0.934994 0.029094 0.033 Uiso 1 1 calc R U . . .
 H31C H 0.245472 1.031220 0.110893 0.033 Uiso 1 1 calc R U . . .
 Br2 Br 0.57230(10) -0.12825(9) 0.78978(6) 0.0283(3) Uani 1 1 d . . . . .
 O4 O 0.7648(8) 0.1553(7) 0.9788(4) 0.0241(15) Uani 1 1 d . . . . .
 O5 O 0.4164(8) 0.4375(7) 0.7908(4) 0.0210(14) Uani 1 1 d . . . . .
 O6 O 0.1128(8) 0.4151(9) 0.8720(4) 0.0336(17) Uani 1 1 d . . . . .
 C32 C 0.5682(11) 0.0561(10) 0.8270(6) 0.0212(19) Uani 1 1 d . . . . .
 C33 C 0.6656(11) 0.0465(10) 0.8869(6) 0.0222(19) Uani 1 1 d . . . . .
 H33 H 0.725249 -0.045167 0.906623 0.027 Uiso 1 1 calc R U . . .
 C34 C 0.6737(11) 0.1727(10) 0.9171(5) 0.0175(18) Uani 1 1 d . . . . .
 C35 C 0.5918(10) 0.3055(10) 0.8856(6) 0.0170(18) Uani 1 1 d . . . . .
 H35 H 0.601298 0.392384 0.904288 0.020 Uiso 1 1 calc R U . . .
 C36 C 0.4950(11) 0.3094(9) 0.8258(5) 0.0173(18) Uani 1 1 d . . . . .
 C37 C 0.4760(11) 0.1846(10) 0.7954(5) 0.0183(18) Uani 1 1 d . . . . .
 C38 C 0.7865(13) 0.2821(13) 1.0092(7) 0.032(2) Uani 1 1 d . . . . .
 H38A H 0.824271 0.336006 0.962804 0.047 Uiso 1 1 calc R U . . .
 H38B H 0.868962 0.252813 1.045721 0.047 Uiso 1 1 calc R U . . .
 H38C H 0.681149 0.344030 1.039740 0.047 Uiso 1 1 calc R U . . .
 C39 C 0.3788(16) 0.5696(11) 0.8371(7) 0.040(3) Uani 1 1 d . . . . .
 H39A H 0.309185 0.650990 0.809048 0.060 Uiso 1 1 calc R U . . .
 H39B H 0.481684 0.587005 0.841458 0.060 Uiso 1 1 calc R U . . .
 H39C H 0.319967 0.560437 0.892346 0.060 Uiso 1 1 calc R U . . .
 C40 C 0.3638(11) 0.1893(10) 0.7323(5) 0.0187(18) Uani 1 1 d . . . . .
 H40 H 0.399492 0.085886 0.713573 0.022 Uiso 1 1 calc R U . . .
 C41 C 0.3271(11) 0.4141(10) 0.6384(6) 0.0199(18) Uani 1 1 d . . . . .
 H41 H 0.252368 0.475944 0.681077 0.024 Uiso 1 1 calc R U . . .
 C42 C 0.3611(15) 0.4699(13) 0.5613(7) 0.029(3) Uani 1 1 d . . . . .
 H42 H 0.305075 0.569071 0.551664 0.035 Uiso 1 1 calc R U . . .
 C43 C 0.4719(13) 0.3878(12) 0.4987(6) 0.028(2) Uani 1 1 d . . . . .
 H43 H 0.493844 0.429231 0.446589 0.034 Uiso 1 1 calc R U . . .
 C44 C 0.5522(13) 0.2423(12) 0.5125(6) 0.030(2) Uani 1 1 d . . . . .
 H44 H 0.630845 0.183246 0.469934 0.036 Uiso 1 1 calc R U . . .
 C45 C 0.5171(11) 0.1839(10) 0.5886(5) 0.0194(18) Uani 1 1 d . . . . .
 H45 H 0.572196 0.084191 0.597224 0.023 Uiso 1 1 calc R U . . .
 C46 C 0.4017(11) 0.2678(10) 0.6539(6) 0.0201(19) Uani 1 1 d . . . . .
 C47 C 0.1741(11) 0.2237(11) 0.7676(5) 0.0216(19) Uani 1 1 d . . . . .
 C48 C 0.0854(11) 0.3761(11) 0.8072(5) 0.022(2) Uani 1 1 d . . . . .
 C49 C -0.0489(12) 0.4552(11) 0.7653(6) 0.028(2) Uani 1 1 d . . . . .
 H49 H -0.121017 0.551145 0.778622 0.033 Uiso 1 1 calc R U . . .
 C50 C -0.0564(11) 0.3708(10) 0.7035(5) 0.0204(19) Uani 1 1 d . . . . .
 C51 C 0.0774(11) 0.2241(10) 0.6965(6) 0.0181(19) Uani 1 1 d . . . . .
 H51 H 0.154158 0.221680 0.643467 0.022 Uiso 1 1 calc R U . . .
 C52 C 0.1549(13) 0.1122(12) 0.8341(6) 0.027(2) Uani 1 1 d . . . . .
 H52A H 0.195074 0.014928 0.809200 0.041 Uiso 1 1 calc R U . . .
 H52B H 0.038057 0.135793 0.858748 0.041 Uiso 1 1 calc R U . . .
 H52C H 0.219151 0.114846 0.876841 0.041 Uiso 1 1 calc R U . . .
 C53 C -0.1827(12) 0.4023(10) 0.6469(6) 0.027(2) Uani 1 1 d . . . . .
 H53 H -0.259583 0.347025 0.667786 0.033 Uiso 1 1 calc R U . . .
 C54 C -0.1069(14) 0.3522(12) 0.5570(6) 0.031(2) Uani 1 1 d . . . . .
 H54A H -0.197451 0.381069 0.524294 0.038 Uiso 1 1 calc R U . . .
 H54B H -0.030858 0.406709 0.535589 0.038 Uiso 1 1 calc R U . . .
 C55 C -0.0124(13) 0.1906(11) 0.5407(6) 0.030(2) Uani 1 1 d . . . . .
 H55A H -0.041611 0.160726 0.490561 0.035 Uiso 1 1 calc R U . . .
 H55B H 0.107412 0.176343 0.529578 0.035 Uiso 1 1 calc R U . . .
 C56 C -0.0463(12) 0.0923(11) 0.6109(6) 0.024(2) Uani 1 1 d . . . . .
 H56 H -0.154729 0.075397 0.615416 0.029 Uiso 1 1 calc R U . . .
 C57 C 0.0051(11) 0.1042(10) 0.6924(6) 0.0209(19) Uani 1 1 d . . . . .
 H57 H -0.074908 0.095436 0.742139 0.025 Uiso 1 1 calc R U . . .
 C58 C -0.2872(15) 0.5634(12) 0.6482(8) 0.039(3) Uani 1 1 d . . . . .
 H58A H -0.332055 0.596511 0.705278 0.059 Uiso 1 1 calc R U . . .
 H58B H -0.378185 0.576555 0.617889 0.059 Uiso 1 1 calc R U . . .
 H58C H -0.217959 0.620088 0.622303 0.059 Uiso 1 1 calc R U . . .
 C59 C 0.0879(12) -0.0312(11) 0.6412(6) 0.027(2) Uani 1 1 d . . . . .
 C60 C 0.2672(13) -0.0719(12) 0.5996(8) 0.036(3) Uani 1 1 d . . . . .
 H60A H 0.283829 -0.129399 0.549817 0.054 Uiso 1 1 calc R U . . .
 H60B H 0.338531 -0.128978 0.637415 0.054 Uiso 1 1 calc R U . . .
 H60C H 0.294922 0.016462 0.584871 0.054 Uiso 1 1 calc R U . . .
 C61 C 0.0400(14) -0.1623(12) 0.6728(8) 0.039(3) Uani 1 1 d . . . . .
 H61A H -0.077836 -0.131172 0.696323 0.058 Uiso 1 1 calc R U . . .
 H61B H 0.104945 -0.209700 0.715202 0.058 Uiso 1 1 calc R U . . .
 H61C H 0.061971 -0.230662 0.627195 0.058 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Br1 C1 1.938(9) . ?
 O1 C3 1.372(10) . ?
 O1 C7 1.435(11) . ?
 O2 C5 1.360(10) . ?
 O2 C8 1.427(11) . ?
 O3 C17 1.217(11) . ?
 C1 C2 1.395(13) . ?
 C1 C6 1.375(12) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.368(12) . ?
 C3 C4 1.392(12) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.396(12) . ?
 C5 C6 1.404(12) . ?
 C6 C9 1.544(12) . ?
 C7 H7A 0.9800 . ?
 C7 H7B 0.9800 . ?
 C7 H7C 0.9800 . ?
 C8 H8A 0.9800 . ?
 C8 H8B 0.9800 . ?
 C8 H8C 0.9800 . ?
 C9 H9 1.0000 . ?
 C9 C15 1.530(12) . ?
 C9 C16 1.580(12) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.410(13) . ?
 C10 C15 1.403(12) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.398(15) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.392(15) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.378(14) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.395(13) . ?
 C16 C17 1.529(12) . ?
 C16 C21 1.538(12) . ?
 C16 C27 1.567(12) . ?
 C17 C18 1.460(13) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.327(13) . ?
 C19 C22 1.507(13) . ?
 C19 C27 1.515(11) . ?
 C21 H21A 0.9800 . ?
 C21 H21B 0.9800 . ?
 C21 H21C 0.9800 . ?
 C22 H22 1.0000 . ?
 C22 C23 1.545(14) . ?
 C22 C28 1.533(13) . ?
 C23 H23A 0.9900 . ?
 C23 H23B 0.9900 . ?
 C23 C24 1.563(15) . ?
 C24 H24A 0.9900 . ?
 C24 H24B 0.9900 . ?
 C24 C25 1.506(14) . ?
 C25 H25 1.0000 . ?
 C25 C26 1.519(12) . ?
 C25 C29 1.539(12) . ?
 C26 H26 1.0000 . ?
 C26 C27 1.502(12) . ?
 C26 C29 1.531(12) . ?
 C27 H27 1.0000 . ?
 C28 H28A 0.9800 . ?
 C28 H28B 0.9800 . ?
 C28 H28C 0.9800 . ?
 C29 C30 1.518(13) . ?
 C29 C31 1.501(12) . ?
 C30 H30A 0.9800 . ?
 C30 H30B 0.9800 . ?
 C30 H30C 0.9800 . ?
 C31 H31A 0.9800 . ?
 C31 H31B 0.9800 . ?
 C31 H31C 0.9800 . ?
 Br2 C32 1.917(9) . ?
 O4 C34 1.368(11) . ?
 O4 C38 1.438(12) . ?
 O5 C36 1.370(11) . ?
 O5 C39 1.443(12) . ?
 O6 C48 1.238(11) . ?
 C32 C33 1.392(13) . ?
 C32 C37 1.383(13) . ?
 C33 H33 0.9500 . ?
 C33 C34 1.378(13) . ?
 C34 C35 1.385(14) . ?
 C35 H35 0.9500 . ?
 C35 C36 1.397(13) . ?
 C36 C37 1.409(13) . ?
 C37 C40 1.537(12) . ?
 C38 H38A 0.9800 . ?
 C38 H38B 0.9800 . ?
 C38 H38C 0.9800 . ?
 C39 H39A 0.9800 . ?
 C39 H39B 0.9800 . ?
 C39 H39C 0.9800 . ?
 C40 H40 1.0000 . ?
 C40 C46 1.515(12) . ?
 C40 C47 1.579(12) . ?
 C41 H41 0.9500 . ?
 C41 C42 1.385(14) . ?
 C41 C46 1.393(13) . ?
 C42 H42 0.9500 . ?
 C42 C43 1.363(16) . ?
 C43 H43 0.9500 . ?
 C43 C44 1.389(16) . ?
 C44 H44 0.9500 . ?
 C44 C45 1.382(13) . ?
 C45 H45 0.9500 . ?
 C45 C46 1.415(12) . ?
 C47 C48 1.547(13) . ?
 C47 C51 1.558(12) . ?
 C47 C52 1.539(13) . ?
 C48 C49 1.442(13) . ?
 C49 H49 0.9500 . ?
 C49 C50 1.364(14) . ?
 C50 C51 1.513(13) . ?
 C50 C53 1.512(13) . ?
 C51 H51 1.0000 . ?
 C51 C57 1.510(13) . ?
 C52 H52A 0.9800 . ?
 C52 H52B 0.9800 . ?
 C52 H52C 0.9800 . ?
 C53 H53 1.0000 . ?
 C53 C54 1.544(14) . ?
 C53 C58 1.535(14) . ?
 C54 H54A 0.9900 . ?
 C54 H54B 0.9900 . ?
 C54 C55 1.531(15) . ?
 C55 H55A 0.9900 . ?
 C55 H55B 0.9900 . ?
 C55 C56 1.522(14) . ?
 C56 H56 1.0000 . ?
 C56 C57 1.511(13) . ?
 C56 C59 1.513(13) . ?
 C57 H57 1.0000 . ?
 C57 C59 1.497(13) . ?
 C58 H58A 0.9800 . ?
 C58 H58B 0.9800 . ?
 C58 H58C 0.9800 . ?
 C59 C60 1.517(14) . ?
 C59 C61 1.517(15) . ?
 C60 H60A 0.9800 . ?
 C60 H60B 0.9800 . ?
 C60 H60C 0.9800 . ?
 C61 H61A 0.9800 . ?
 C61 H61B 0.9800 . ?
 C61 H61C 0.9800 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C3 O1 C7 117.0(7) . . ?
 C5 O2 C8 117.7(7) . . ?
 C2 C1 Br1 113.2(6) . . ?
 C6 C1 Br1 121.4(7) . . ?
 C6 C1 C2 125.4(8) . . ?
 C1 C2 H2 121.6 . . ?
 C3 C2 C1 116.9(8) . . ?
 C3 C2 H2 121.6 . . ?
 O1 C3 C4 114.3(7) . . ?
 C2 C3 O1 124.4(8) . . ?
 C2 C3 C4 121.2(8) . . ?
 C3 C4 H4 120.2 . . ?
 C3 C4 C5 119.6(8) . . ?
 C5 C4 H4 120.2 . . ?
 O2 C5 C4 121.9(8) . . ?
 O2 C5 C6 116.8(8) . . ?
 C4 C5 C6 121.3(8) . . ?
 C1 C6 C5 115.4(8) . . ?
 C1 C6 C9 122.6(7) . . ?
 C5 C6 C9 122.0(7) . . ?
 O1 C7 H7A 109.5 . . ?
 O1 C7 H7B 109.5 . . ?
 O1 C7 H7C 109.5 . . ?
 H7A C7 H7B 109.5 . . ?
 H7A C7 H7C 109.5 . . ?
 H7B C7 H7C 109.5 . . ?
 O2 C8 H8A 109.5 . . ?
 O2 C8 H8B 109.5 . . ?
 O2 C8 H8C 109.5 . . ?
 H8A C8 H8B 109.5 . . ?
 H8A C8 H8C 109.5 . . ?
 H8B C8 H8C 109.5 . . ?
 C6 C9 H9 103.1 . . ?
 C6 C9 C16 115.1(7) . . ?
 C15 C9 C6 115.1(7) . . ?
 C15 C9 H9 103.1 . . ?
 C15 C9 C16 114.9(7) . . ?
 C16 C9 H9 103.1 . . ?
 C11 C10 H10 119.7 . . ?
 C15 C10 H10 119.7 . . ?
 C15 C10 C11 120.7(9) . . ?
 C10 C11 H11 119.7 . . ?
 C12 C11 C10 120.6(9) . . ?
 C12 C11 H11 119.7 . . ?
 C11 C12 H12 120.8 . . ?
 C13 C12 C11 118.5(9) . . ?
 C13 C12 H12 120.8 . . ?
 C12 C13 H13 119.7 . . ?
 C14 C13 C12 120.5(9) . . ?
 C14 C13 H13 119.7 . . ?
 C13 C14 H14 118.7 . . ?
 C13 C14 C15 122.6(9) . . ?
 C15 C14 H14 118.7 . . ?
 C10 C15 C9 124.7(8) . . ?
 C14 C15 C9 118.1(8) . . ?
 C14 C15 C10 117.1(8) . . ?
 C17 C16 C9 118.0(7) . . ?
 C17 C16 C21 105.5(7) . . ?
 C17 C16 C27 103.7(7) . . ?
 C21 C16 C9 108.3(7) . . ?
 C21 C16 C27 112.1(7) . . ?
 C27 C16 C9 109.2(7) . . ?
 O3 C17 C16 123.8(8) . . ?
 O3 C17 C18 127.5(8) . . ?
 C18 C17 C16 108.1(7) . . ?
 C17 C18 H18 124.1 . . ?
 C19 C18 C17 111.8(8) . . ?
 C19 C18 H18 124.1 . . ?
 C18 C19 C22 129.0(8) . . ?
 C18 C19 C27 111.8(8) . . ?
 C22 C19 C27 119.0(8) . . ?
 C16 C21 H21A 109.5 . . ?
 C16 C21 H21B 109.5 . . ?
 C16 C21 H21C 109.5 . . ?
 H21A C21 H21B 109.5 . . ?
 H21A C21 H21C 109.5 . . ?
 H21B C21 H21C 109.5 . . ?
 C19 C22 H22 107.1 . . ?
 C19 C22 C23 113.9(8) . . ?
 C19 C22 C28 111.9(9) . . ?
 C23 C22 H22 107.1 . . ?
 C28 C22 H22 107.1 . . ?
 C28 C22 C23 109.4(8) . . ?
 C22 C23 H23A 107.9 . . ?
 C22 C23 H23B 107.9 . . ?
 C22 C23 C24 117.5(8) . . ?
 H23A C23 H23B 107.2 . . ?
 C24 C23 H23A 107.9 . . ?
 C24 C23 H23B 107.9 . . ?
 C23 C24 H24A 108.4 . . ?
 C23 C24 H24B 108.4 . . ?
 H24A C24 H24B 107.4 . . ?
 C25 C24 C23 115.7(10) . . ?
 C25 C24 H24A 108.4 . . ?
 C25 C24 H24B 108.4 . . ?
 C24 C25 H25 115.2 . . ?
 C24 C25 C26 117.2(8) . . ?
 C24 C25 C29 122.7(8) . . ?
 C26 C25 H25 115.2 . . ?
 C26 C25 C29 60.1(6) . . ?
 C29 C25 H25 115.2 . . ?
 C25 C26 H26 115.0 . . ?
 C25 C26 C29 60.6(6) . . ?
 C27 C26 C25 116.9(8) . . ?
 C27 C26 H26 115.0 . . ?
 C27 C26 C29 123.3(7) . . ?
 C29 C26 H26 115.0 . . ?
 C16 C27 H27 107.8 . . ?
 C19 C27 C16 104.5(7) . . ?
 C19 C27 H27 107.8 . . ?
 C26 C27 C16 118.7(7) . . ?
 C26 C27 C19 109.9(7) . . ?
 C26 C27 H27 107.8 . . ?
 C22 C28 H28A 109.5 . . ?
 C22 C28 H28B 109.5 . . ?
 C22 C28 H28C 109.5 . . ?
 H28A C28 H28B 109.5 . . ?
 H28A C28 H28C 109.5 . . ?
 H28B C28 H28C 109.5 . . ?
 C26 C29 C25 59.3(6) . . ?
 C30 C29 C25 116.7(8) . . ?
 C30 C29 C26 116.2(8) . . ?
 C31 C29 C25 120.4(8) . . ?
 C31 C29 C26 121.8(7) . . ?
 C31 C29 C30 112.7(8) . . ?
 C29 C30 H30A 109.5 . . ?
 C29 C30 H30B 109.5 . . ?
 C29 C30 H30C 109.5 . . ?
 H30A C30 H30B 109.5 . . ?
 H30A C30 H30C 109.5 . . ?
 H30B C30 H30C 109.5 . . ?
 C29 C31 H31A 109.5 . . ?
 C29 C31 H31B 109.5 . . ?
 C29 C31 H31C 109.5 . . ?
 H31A C31 H31B 109.5 . . ?
 H31A C31 H31C 109.5 . . ?
 H31B C31 H31C 109.5 . . ?
 C34 O4 C38 117.9(8) . . ?
 C36 O5 C39 117.8(7) . . ?
 C33 C32 Br2 113.9(7) . . ?
 C37 C32 Br2 121.5(7) . . ?
 C37 C32 C33 124.6(9) . . ?
 C32 C33 H33 120.7 . . ?
 C34 C33 C32 118.7(9) . . ?
 C34 C33 H33 120.7 . . ?
 O4 C34 C33 115.4(8) . . ?
 O4 C34 C35 124.4(8) . . ?
 C33 C34 C35 120.2(8) . . ?
 C34 C35 H35 120.6 . . ?
 C34 C35 C36 118.9(8) . . ?
 C36 C35 H35 120.6 . . ?
 O5 C36 C35 120.9(8) . . ?
 O5 C36 C37 115.6(8) . . ?
 C35 C36 C37 123.4(8) . . ?
 C32 C37 C36 114.1(8) . . ?
 C32 C37 C40 122.5(8) . . ?
 C36 C37 C40 123.4(8) . . ?
 O4 C38 H38A 109.5 . . ?
 O4 C38 H38B 109.5 . . ?
 O4 C38 H38C 109.5 . . ?
 H38A C38 H38B 109.5 . . ?
 H38A C38 H38C 109.5 . . ?
 H38B C38 H38C 109.5 . . ?
 O5 C39 H39A 109.5 . . ?
 O5 C39 H39B 109.5 . . ?
 O5 C39 H39C 109.5 . . ?
 H39A C39 H39B 109.5 . . ?
 H39A C39 H39C 109.5 . . ?
 H39B C39 H39C 109.5 . . ?
 C37 C40 H40 103.1 . . ?
 C37 C40 C47 116.3(7) . . ?
 C46 C40 C37 113.8(7) . . ?
 C46 C40 H40 103.1 . . ?
 C46 C40 C47 115.0(7) . . ?
 C47 C40 H40 103.1 . . ?
 C42 C41 H41 119.8 . . ?
 C42 C41 C46 120.4(9) . . ?
 C46 C41 H41 119.8 . . ?
 C41 C42 H42 118.8 . . ?
 C43 C42 C41 122.4(11) . . ?
 C43 C42 H42 118.8 . . ?
 C42 C43 H43 120.6 . . ?
 C42 C43 C44 118.8(9) . . ?
 C44 C43 H43 120.6 . . ?
 C43 C44 H44 120.2 . . ?
 C45 C44 C43 119.6(9) . . ?
 C45 C44 H44 120.2 . . ?
 C44 C45 H45 118.9 . . ?
 C44 C45 C46 122.2(9) . . ?
 C46 C45 H45 118.9 . . ?
 C41 C46 C40 126.1(8) . . ?
 C41 C46 C45 116.5(8) . . ?
 C45 C46 C40 117.4(8) . . ?
 C48 C47 C40 115.2(8) . . ?
 C48 C47 C51 103.1(7) . . ?
 C51 C47 C40 110.2(7) . . ?
 C52 C47 C40 108.7(7) . . ?
 C52 C47 C48 107.2(8) . . ?
 C52 C47 C51 112.5(8) . . ?
 O6 C48 C47 124.0(8) . . ?
 O6 C48 C49 125.4(9) . . ?
 C49 C48 C47 110.0(8) . . ?
 C48 C49 H49 125.3 . . ?
 C50 C49 C48 109.4(9) . . ?
 C50 C49 H49 125.3 . . ?
 C49 C50 C51 112.9(8) . . ?
 C49 C50 C53 128.8(8) . . ?
 C53 C50 C51 118.3(8) . . ?
 C47 C51 H51 107.4 . . ?
 C50 C51 C47 104.6(7) . . ?
 C50 C51 H51 107.4 . . ?
 C57 C51 C47 118.8(8) . . ?
 C57 C51 C50 110.8(8) . . ?
 C57 C51 H51 107.4 . . ?
 C47 C52 H52A 109.5 . . ?
 C47 C52 H52B 109.5 . . ?
 C47 C52 H52C 109.5 . . ?
 H52A C52 H52B 109.5 . . ?
 H52A C52 H52C 109.5 . . ?
 H52B C52 H52C 109.5 . . ?
 C50 C53 H53 107.2 . . ?
 C50 C53 C54 113.6(8) . . ?
 C50 C53 C58 112.2(8) . . ?
 C54 C53 H53 107.2 . . ?
 C58 C53 H53 107.2 . . ?
 C58 C53 C54 109.2(9) . . ?
 C53 C54 H54A 107.8 . . ?
 C53 C54 H54B 107.8 . . ?
 H54A C54 H54B 107.2 . . ?
 C55 C54 C53 117.9(8) . . ?
 C55 C54 H54A 107.8 . . ?
 C55 C54 H54B 107.8 . . ?
 C54 C55 H55A 108.7 . . ?
 C54 C55 H55B 108.7 . . ?
 H55A C55 H55B 107.6 . . ?
 C56 C55 C54 114.4(9) . . ?
 C56 C55 H55A 108.7 . . ?
 C56 C55 H55B 108.7 . . ?
 C55 C56 H56 114.5 . . ?
 C57 C56 C55 119.4(8) . . ?
 C57 C56 H56 114.5 . . ?
 C57 C56 C59 59.4(6) . . ?
 C59 C56 C55 123.3(9) . . ?
 C59 C56 H56 114.5 . . ?
 C51 C57 C56 114.2(8) . . ?
 C51 C57 H57 115.2 . . ?
 C56 C57 H57 115.2 . . ?
 C59 C57 C51 124.6(8) . . ?
 C59 C57 C56 60.4(6) . . ?
 C59 C57 H57 115.2 . . ?
 C53 C58 H58A 109.5 . . ?
 C53 C58 H58B 109.5 . . ?
 C53 C58 H58C 109.5 . . ?
 H58A C58 H58B 109.5 . . ?
 H58A C58 H58C 109.5 . . ?
 H58B C58 H58C 109.5 . . ?
 C56 C59 C60 121.8(9) . . ?
 C56 C59 C61 115.9(9) . . ?
 C57 C59 C56 60.3(6) . . ?
 C57 C59 C60 121.7(9) . . ?
 C57 C59 C61 115.5(9) . . ?
 C61 C59 C60 112.5(9) . . ?
 C59 C60 H60A 109.5 . . ?
 C59 C60 H60B 109.5 . . ?
 C59 C60 H60C 109.5 . . ?
 H60A C60 H60B 109.5 . . ?
 H60A C60 H60C 109.5 . . ?
 H60B C60 H60C 109.5 . . ?
 C59 C61 H61A 109.5 . . ?
 C59 C61 H61B 109.5 . . ?
 C59 C61 H61C 109.5 . . ?
 H61A C61 H61B 109.5 . . ?
 H61A C61 H61C 109.5 . . ?
 H61B C61 H61C 109.5 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 Br1 C1 C2 C3 -177.7(6) . . . . ?
 Br1 C1 C6 C5 -178.3(6) . . . . ?
 Br1 C1 C6 C9 1.8(11) . . . . ?
 O1 C3 C4 C5 178.8(7) . . . . ?
 O2 C5 C6 C1 174.2(7) . . . . ?
 O2 C5 C6 C9 -5.8(12) . . . . ?
 O3 C17 C18 C19 -169.1(9) . . . . ?
 C1 C2 C3 O1 178.6(8) . . . . ?
 C1 C2 C3 C4 -3.6(13) . . . . ?
 C1 C6 C9 C15 -121.3(9) . . . . ?
 C1 C6 C9 C16 101.6(9) . . . . ?
 C2 C1 C6 C5 1.4(13) . . . . ?
 C2 C1 C6 C9 -178.5(8) . . . . ?
 C2 C3 C4 C5 0.9(13) . . . . ?
 C3 C4 C5 O2 -175.2(8) . . . . ?
 C3 C4 C5 C6 3.4(13) . . . . ?
 C4 C5 C6 C1 -4.4(12) . . . . ?
 C4 C5 C6 C9 175.6(8) . . . . ?
 C5 C6 C9 C15 58.8(11) . . . . ?
 C5 C6 C9 C16 -78.3(10) . . . . ?
 C6 C1 C2 C3 2.5(13) . . . . ?
 C6 C9 C15 C10 -93.5(10) . . . . ?
 C6 C9 C15 C14 90.2(9) . . . . ?
 C6 C9 C16 C17 66.1(10) . . . . ?
 C6 C9 C16 C21 -53.6(9) . . . . ?
 C6 C9 C16 C27 -176.0(7) . . . . ?
 C7 O1 C3 C2 13.1(12) . . . . ?
 C7 O1 C3 C4 -164.8(8) . . . . ?
 C8 O2 C5 C4 -19.6(12) . . . . ?
 C8 O2 C5 C6 161.8(8) . . . . ?
 C9 C16 C17 O3 -67.7(11) . . . . ?
 C9 C16 C17 C18 120.8(8) . . . . ?
 C9 C16 C27 C19 -128.3(7) . . . . ?
 C9 C16 C27 C26 108.9(8) . . . . ?
 C10 C11 C12 C13 1.7(15) . . . . ?
 C11 C10 C15 C9 -173.7(8) . . . . ?
 C11 C10 C15 C14 2.6(13) . . . . ?
 C11 C12 C13 C14 -0.3(15) . . . . ?
 C12 C13 C14 C15 0.0(15) . . . . ?
 C13 C14 C15 C9 175.3(9) . . . . ?
 C13 C14 C15 C10 -1.2(13) . . . . ?
 C15 C9 C16 C17 -71.1(10) . . . . ?
 C15 C9 C16 C21 169.2(7) . . . . ?
 C15 C9 C16 C27 46.8(9) . . . . ?
 C15 C10 C11 C12 -2.9(14) . . . . ?
 C16 C9 C15 C10 43.7(11) . . . . ?
 C16 C9 C15 C14 -132.5(8) . . . . ?
 C16 C17 C18 C19 2.0(11) . . . . ?
 C17 C16 C27 C19 -1.7(8) . . . . ?
 C17 C16 C27 C26 -124.5(8) . . . . ?
 C17 C18 C19 C22 172.5(9) . . . . ?
 C17 C18 C19 C27 -3.2(11) . . . . ?
 C18 C19 C22 C23 141.2(10) . . . . ?
 C18 C19 C22 C28 16.5(14) . . . . ?
 C18 C19 C27 C16 3.1(10) . . . . ?
 C18 C19 C27 C26 131.5(8) . . . . ?
 C19 C22 C23 C24 59.4(12) . . . . ?
 C21 C16 C17 O3 53.5(11) . . . . ?
 C21 C16 C17 C18 -118.0(8) . . . . ?
 C21 C16 C27 C19 111.7(8) . . . . ?
 C21 C16 C27 C26 -11.2(10) . . . . ?
 C22 C19 C27 C16 -173.1(8) . . . . ?
 C22 C19 C27 C26 -44.7(11) . . . . ?
 C22 C23 C24 C25 18.1(14) . . . . ?
 C23 C24 C25 C26 -63.1(12) . . . . ?
 C23 C24 C25 C29 -133.4(10) . . . . ?
 C24 C25 C26 C27 1.0(12) . . . . ?
 C24 C25 C26 C29 -113.9(9) . . . . ?
 C24 C25 C29 C26 104.9(10) . . . . ?
 C24 C25 C29 C30 -149.1(9) . . . . ?
 C24 C25 C29 C31 -6.3(14) . . . . ?
 C25 C26 C27 C16 -164.9(7) . . . . ?
 C25 C26 C27 C19 75.0(9) . . . . ?
 C25 C26 C29 C30 -106.9(9) . . . . ?
 C25 C26 C29 C31 109.0(9) . . . . ?
 C26 C25 C29 C30 106.0(9) . . . . ?
 C26 C25 C29 C31 -111.2(9) . . . . ?
 C27 C16 C17 O3 171.5(8) . . . . ?
 C27 C16 C17 C18 0.0(9) . . . . ?
 C27 C19 C22 C23 -43.4(11) . . . . ?
 C27 C19 C22 C28 -168.0(8) . . . . ?
 C27 C26 C29 C25 -104.6(9) . . . . ?
 C27 C26 C29 C30 148.5(8) . . . . ?
 C27 C26 C29 C31 4.4(13) . . . . ?
 C28 C22 C23 C24 -174.5(9) . . . . ?
 C29 C25 C26 C27 114.8(8) . . . . ?
 C29 C26 C27 C16 -93.8(10) . . . . ?
 C29 C26 C27 C19 146.0(8) . . . . ?
 Br2 C32 C33 C34 179.0(7) . . . . ?
 Br2 C32 C37 C36 -176.2(6) . . . . ?
 Br2 C32 C37 C40 3.5(12) . . . . ?
 O4 C34 C35 C36 -176.4(8) . . . . ?
 O5 C36 C37 C32 174.8(8) . . . . ?
 O5 C36 C37 C40 -4.9(12) . . . . ?
 O6 C48 C49 C50 -170.8(10) . . . . ?
 C32 C33 C34 O4 176.7(8) . . . . ?
 C32 C33 C34 C35 -2.7(14) . . . . ?
 C32 C37 C40 C46 -124.3(9) . . . . ?
 C32 C37 C40 C47 98.5(10) . . . . ?
 C33 C32 C37 C36 3.3(13) . . . . ?
 C33 C32 C37 C40 -176.9(8) . . . . ?
 C33 C34 C35 C36 3.0(13) . . . . ?
 C34 C35 C36 O5 -177.7(8) . . . . ?
 C34 C35 C36 C37 -0.1(13) . . . . ?
 C35 C36 C37 C32 -2.9(13) . . . . ?
 C35 C36 C37 C40 177.3(8) . . . . ?
 C36 C37 C40 C46 55.4(11) . . . . ?
 C36 C37 C40 C47 -81.8(11) . . . . ?
 C37 C32 C33 C34 -0.6(14) . . . . ?
 C37 C40 C46 C41 -92.9(11) . . . . ?
 C37 C40 C46 C45 90.7(10) . . . . ?
 C37 C40 C47 C48 64.2(10) . . . . ?
 C37 C40 C47 C51 -179.8(8) . . . . ?
 C37 C40 C47 C52 -56.1(10) . . . . ?
 C38 O4 C34 C33 176.1(8) . . . . ?
 C38 O4 C34 C35 -4.5(13) . . . . ?
 C39 O5 C36 C35 -24.7(13) . . . . ?
 C39 O5 C36 C37 157.5(9) . . . . ?
 C40 C47 C48 O6 -68.1(12) . . . . ?
 C40 C47 C48 C49 120.9(9) . . . . ?
 C40 C47 C51 C50 -124.9(8) . . . . ?
 C40 C47 C51 C57 111.0(9) . . . . ?
 C41 C42 C43 C44 0.8(17) . . . . ?
 C42 C41 C46 C40 -173.7(9) . . . . ?
 C42 C41 C46 C45 2.8(14) . . . . ?
 C42 C43 C44 C45 0.7(15) . . . . ?
 C43 C44 C45 C46 -0.4(14) . . . . ?
 C44 C45 C46 C40 175.4(9) . . . . ?
 C44 C45 C46 C41 -1.3(13) . . . . ?
 C46 C40 C47 C48 -72.5(10) . . . . ?
 C46 C40 C47 C51 43.5(11) . . . . ?
 C46 C40 C47 C52 167.2(8) . . . . ?
 C46 C41 C42 C43 -2.6(17) . . . . ?
 C47 C40 C46 C41 44.9(13) . . . . ?
 C47 C40 C46 C45 -131.6(8) . . . . ?
 C47 C48 C49 C50 0.1(11) . . . . ?
 C47 C51 C57 C56 -165.0(8) . . . . ?
 C47 C51 C57 C59 -95.4(11) . . . . ?
 C48 C47 C51 C50 -1.4(9) . . . . ?
 C48 C47 C51 C57 -125.6(9) . . . . ?
 C48 C49 C50 C51 -1.1(12) . . . . ?
 C48 C49 C50 C53 175.3(10) . . . . ?
 C49 C50 C51 C47 1.6(11) . . . . ?
 C49 C50 C51 C57 130.8(9) . . . . ?
 C49 C50 C53 C54 140.1(10) . . . . ?
 C49 C50 C53 C58 15.6(15) . . . . ?
 C50 C51 C57 C56 73.9(10) . . . . ?
 C50 C51 C57 C59 143.5(9) . . . . ?
 C50 C53 C54 C55 60.2(12) . . . . ?
 C51 C47 C48 O6 171.9(9) . . . . ?
 C51 C47 C48 C49 0.9(10) . . . . ?
 C51 C50 C53 C54 -43.6(12) . . . . ?
 C51 C50 C53 C58 -168.1(9) . . . . ?
 C51 C57 C59 C56 -100.4(10) . . . . ?
 C51 C57 C59 C60 10.7(15) . . . . ?
 C51 C57 C59 C61 153.1(9) . . . . ?
 C52 C47 C48 O6 53.0(12) . . . . ?
 C52 C47 C48 C49 -118.0(9) . . . . ?
 C52 C47 C51 C50 113.7(9) . . . . ?
 C52 C47 C51 C57 -10.5(12) . . . . ?
 C53 C50 C51 C47 -175.2(8) . . . . ?
 C53 C50 C51 C57 -46.0(11) . . . . ?
 C53 C54 C55 C56 17.0(13) . . . . ?
 C54 C55 C56 C57 -65.0(12) . . . . ?
 C54 C55 C56 C59 -135.8(10) . . . . ?
 C55 C56 C57 C51 3.9(12) . . . . ?
 C55 C56 C57 C59 -113.5(10) . . . . ?
 C55 C56 C59 C57 107.1(10) . . . . ?
 C55 C56 C59 C60 -3.9(14) . . . . ?
 C55 C56 C59 C61 -147.1(10) . . . . ?
 C56 C57 C59 C60 111.1(11) . . . . ?
 C56 C57 C59 C61 -106.6(10) . . . . ?
 C57 C56 C59 C60 -110.9(10) . . . . ?
 C57 C56 C59 C61 105.8(10) . . . . ?
 C58 C53 C54 C55 -173.7(9) . . . . ?
 C59 C56 C57 C51 117.4(9) . . . . ?

_olex2_exptl_crystal_mounting_method  'oil flash cooled to 100K'
_olex2_submission_special_instructions  'No special instructions were received'


 
data_chai054 
  
_audit_creation_method            'SHELXL-2017/1' 
_shelx_SHELXL_version_number      '2017/1' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety 
 'C30 H35 Br O2' 
_chemical_formula_sum 
 'C30 H35 Br O2' 
_chemical_formula_weight          507.49 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Br'  'Br'  -0.6763   1.2805 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            5 
_space_group_name_H-M_alt         'C 2' 
_space_group_name_Hall            'C 2y' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y, -z' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z' 
  
_cell_length_a                    10.5352(9) 
_cell_length_b                    15.6736(13) 
_cell_length_c                    15.3409(13) 
_cell_angle_alpha                 90 
_cell_angle_beta                  91.639(2) 
_cell_angle_gamma                 90 
_cell_volume                      2532.1(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     9666 
_cell_measurement_theta_min       2.88 
_cell_measurement_theta_max       74.99 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.331 
_exptl_crystal_F_000              1064 
_exptl_transmission_factor_min    0.5319 
_exptl_transmission_factor_max    0.7540 
_exptl_crystal_size_max           0.262 
_exptl_crystal_size_mid           0.117 
_exptl_crystal_size_min           0.084 
_exptl_absorpt_coefficient_mu     2.390 
_shelx_estimated_absorpt_T_min    0.573 
_shelx_estimated_absorpt_T_max    0.824 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    'APEX3 (Bruker, 2007)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker AXS APEX diffractometer' 
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  8.33 
_diffrn_reflns_number             20416 
_diffrn_reflns_av_unetI/netI      0.0490 
_diffrn_reflns_av_R_equivalents   0.0537 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -18 
_diffrn_reflns_limit_k_max        19 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          2.882 
_diffrn_reflns_theta_max          75.967 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.981 
_diffrn_measured_fraction_theta_full  0.997 
_diffrn_reflns_Laue_measured_fraction_max    0.981 
_diffrn_reflns_Laue_measured_fraction_full   0.997 
_diffrn_reflns_point_group_measured_fraction_max   0.933 
_diffrn_reflns_point_group_measured_fraction_full  0.965 
_reflns_number_total              4927 
_reflns_number_gt                 4871 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.832 
_reflns_Friedel_fraction_max      0.881 
_reflns_Friedel_fraction_full     0.930 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.1042P)²+10.0623P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      iterative 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2184 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    -0.040(18) 
_chemical_absolute_configuration  rm 
_refine_ls_number_reflns          4927 
_refine_ls_number_parameters      304 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0486 
_refine_ls_R_factor_gt            0.0482 
_refine_ls_wR_factor_ref          0.1297 
_refine_ls_wR_factor_gt           0.1291 
_refine_ls_goodness_of_fit_ref    0.850 
_refine_ls_restrained_S_all       0.850 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Br1 Br 0.60307(5) 0.59291(4) 0.88057(3) 0.02927(19) Uani 1 1 d . . . . . 
O1 O 0.7195(3) 0.2827(3) 0.9763(2) 0.0257(8) Uani 1 1 d . . . . . 
O2 O 0.3554(3) 0.3155(2) 0.7908(2) 0.0238(7) Uani 1 1 d . . . . . 
C1 C 0.3315(6) 0.4072(4) 0.6243(3) 0.0292(12) Uani 1 1 d . . . . . 
H1 H 0.342613 0.350141 0.644022 0.035 Uiso 1 1 calc R U . . . 
C2 C 0.2616(6) 0.4282(4) 0.5533(4) 0.0290(12) Uani 1 1 d . . . . . 
H2 H 0.223290 0.387804 0.514587 0.035 Uiso 1 1 calc R U . . . 
C3 C 0.2513(5) 0.5199(4) 0.5422(3) 0.0231(10) Uani 1 1 d . . . . . 
C4 C 0.1909(5) 0.5602(4) 0.4748(4) 0.0275(12) Uani 1 1 d . . . . . 
C5 C 0.1328(6) 0.5102(5) 0.3986(4) 0.0371(14) Uani 1 1 d . . . . . 
H5A H 0.158653 0.535936 0.343645 0.056 Uiso 1 1 calc R U . . . 
H5B H 0.040047 0.511486 0.401559 0.056 Uiso 1 1 calc R U . . . 
H5C H 0.162382 0.450961 0.401497 0.056 Uiso 1 1 calc R U . . . 
C6 C 0.1691(6) 0.6543(4) 0.4649(4) 0.0312(13) Uani 1 1 d . . . . . 
H6A H 0.080655 0.662887 0.443029 0.037 Uiso 1 1 calc R U . . . 
H6AB H 0.225736 0.675503 0.419294 0.037 Uiso 1 1 calc R U . . . 
C7 C 0.1895(5) 0.7099(4) 0.5455(3) 0.0274(11) Uani 1 1 d . . . . . 
H7A H 0.154957 0.767712 0.533992 0.033 Uiso 1 1 calc R U . . . 
H7AB H 0.143759 0.685097 0.594927 0.033 Uiso 1 1 calc R U . . . 
C8 C 0.3292(5) 0.7160(4) 0.5689(3) 0.0226(10) Uani 1 1 d . . . . . 
H8 H 0.380345 0.746970 0.524980 0.027 Uiso 1 1 calc R U . . . 
C9 C 0.3838(5) 0.7201(4) 0.6609(3) 0.0222(11) Uani 1 1 d . . . . . 
C10 C 0.3943(4) 0.6382(4) 0.6081(3) 0.0206(10) Uani 1 1 d . . . . . 
H10 H 0.480893 0.626777 0.585718 0.025 Uiso 1 1 calc R U . . . 
C11 C 0.2970(6) 0.7291(4) 0.7370(4) 0.0282(11) Uani 1 1 d . . . . . 
H11A H 0.341585 0.710221 0.790521 0.042 Uiso 1 1 calc R U . . . 
H11B H 0.221104 0.693964 0.726785 0.042 Uiso 1 1 calc R U . . . 
H11C H 0.271997 0.788999 0.743086 0.042 Uiso 1 1 calc R U . . . 
C12 C 0.5044(5) 0.7719(4) 0.6724(4) 0.0290(11) Uani 1 1 d . . . . . 
H12A H 0.546237 0.757492 0.728348 0.043 Uiso 1 1 calc R U . . . 
H12B H 0.483606 0.832816 0.671339 0.043 Uiso 1 1 calc R U . . . 
H12C H 0.561549 0.758820 0.624871 0.043 Uiso 1 1 calc R U . . . 
C13 C 0.3168(5) 0.5593(3) 0.6241(3) 0.0193(9) Uani 1 1 d . . . . . 
H13 H 0.247738 0.576353 0.663969 0.023 Uiso 1 1 calc R U . . . 
C14 C 0.3907(5) 0.4833(4) 0.6698(3) 0.0224(11) Uani 1 1 d . . . . . 
C15 C 0.5326(5) 0.4817(4) 0.6486(4) 0.0301(12) Uani 1 1 d . . . . . 
H15A H 0.576096 0.529230 0.678349 0.045 Uiso 1 1 calc R U . . . 
H15B H 0.542100 0.487184 0.585528 0.045 Uiso 1 1 calc R U . . . 
H15C H 0.570095 0.427641 0.668613 0.045 Uiso 1 1 calc R U . . . 
C16 C 0.3815(4) 0.4943(3) 0.7713(3) 0.0173(9) Uani 1 1 d . . . . . 
H16 H 0.414761 0.553350 0.781690 0.021 Uiso 1 1 calc R U . . . 
C17 C 0.1452(5) 0.4521(3) 0.7762(3) 0.0223(10) Uani 1 1 d . . . . . 
H17 H 0.155889 0.413356 0.729286 0.027 Uiso 1 1 calc R U . . . 
C18 C 0.0247(5) 0.4620(4) 0.8124(3) 0.0246(11) Uani 1 1 d . . . . . 
H18 H -0.045486 0.429885 0.790080 0.029 Uiso 1 1 calc R U . . . 
C19 C 0.0085(5) 0.5187(4) 0.8806(3) 0.0234(10) Uani 1 1 d . . . . . 
H19 H -0.072967 0.525962 0.904561 0.028 Uiso 1 1 calc R U . . . 
C20 C 0.1116(5) 0.5647(3) 0.9137(3) 0.0232(10) Uani 1 1 d . . . . . 
H20 H 0.101204 0.603418 0.960603 0.028 Uiso 1 1 calc R U . . . 
C21 C 0.2307(5) 0.5537(3) 0.8778(3) 0.0189(9) Uani 1 1 d . . . . . 
H21 H 0.301344 0.584725 0.901038 0.023 Uiso 1 1 calc R U . . . 
C22 C 0.2475(4) 0.4981(3) 0.8083(3) 0.0177(9) Uani 1 1 d . . . . . 
C23 C 0.5706(5) 0.4732(4) 0.8777(3) 0.0213(9) Uani 1 1 d . . . . . 
C24 C 0.6569(5) 0.4252(3) 0.9288(3) 0.0212(10) Uani 1 1 d . . . . . 
H24 H 0.723921 0.451954 0.961185 0.025 Uiso 1 1 calc R U . . . 
C25 C 0.6414(5) 0.3379(3) 0.9305(3) 0.0211(10) Uani 1 1 d . . . . . 
C26 C 0.5408(5) 0.2995(3) 0.8842(3) 0.0214(9) Uani 1 1 d . . . . . 
H26 H 0.529787 0.239406 0.886145 0.026 Uiso 1 1 calc R U . . . 
C27 C 0.4574(5) 0.3495(3) 0.8353(3) 0.0193(9) Uani 1 1 d . . . . . 
C28 C 0.4708(5) 0.4389(3) 0.8279(3) 0.0187(9) Uani 1 1 d . . . . . 
C29 C 0.8280(6) 0.3191(4) 1.0192(4) 0.0309(12) Uani 1 1 d . . . . . 
H29A H 0.880994 0.273661 1.044724 0.046 Uiso 1 1 calc R U . . . 
H29B H 0.800759 0.357588 1.065421 0.046 Uiso 1 1 calc R U . . . 
H29C H 0.877128 0.351310 0.976961 0.046 Uiso 1 1 calc R U . . . 
C30 C 0.3447(6) 0.2248(3) 0.7901(4) 0.0293(11) Uani 1 1 d . . . . . 
H30A H 0.271010 0.208027 0.753567 0.044 Uiso 1 1 calc R U . . . 
H30B H 0.333817 0.204177 0.849711 0.044 Uiso 1 1 calc R U . . . 
H30C H 0.421798 0.199914 0.766493 0.044 Uiso 1 1 calc R U . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Br1 C23 1.908(6) . ? 
O1 C25 1.374(6) . ? 
O1 C29 1.423(7) . ? 
O2 C27 1.365(6) . ? 
O2 C30 1.427(7) . ? 
C1 C2 1.338(9) . ? 
C1 C14 1.508(8) . ? 
C1 H1 0.9500 . ? 
C2 C3 1.450(8) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.356(8) . ? 
C3 C13 1.545(7) . ? 
C4 C6 1.500(10) . ? 
C4 C5 1.521(8) . ? 
C5 H5A 0.9800 . ? 
C5 H5B 0.9800 . ? 
C5 H5C 0.9800 . ? 
C6 C7 1.523(8) . ? 
C6 H6A 0.9900 . ? 
C6 H6AB 0.9900 . ? 
C7 C8 1.508(7) . ? 
C7 H7A 0.9900 . ? 
C7 H7AB 0.9900 . ? 
C8 C9 1.510(7) . ? 
C8 C10 1.516(7) . ? 
C8 H8 1.0000 . ? 
C9 C11 1.509(7) . ? 
C9 C12 1.514(8) . ? 
C9 C10 1.525(8) . ? 
C10 C13 1.505(7) . ? 
C10 H10 1.0000 . ? 
C11 H11A 0.9800 . ? 
C11 H11B 0.9800 . ? 
C11 H11C 0.9800 . ? 
C12 H12A 0.9800 . ? 
C12 H12B 0.9800 . ? 
C12 H12C 0.9800 . ? 
C13 C14 1.577(8) . ? 
C13 H13 1.0000 . ? 
C14 C15 1.539(8) . ? 
C14 C16 1.574(7) . ? 
C15 H15A 0.9800 . ? 
C15 H15B 0.9800 . ? 
C15 H15C 0.9800 . ? 
C16 C28 1.532(7) . ? 
C16 C22 1.537(6) . ? 
C16 H16 1.0000 . ? 
C17 C22 1.377(7) . ? 
C17 C18 1.409(7) . ? 
C17 H17 0.9500 . ? 
C18 C19 1.386(8) . ? 
C18 H18 0.9500 . ? 
C19 C20 1.389(8) . ? 
C19 H19 0.9500 . ? 
C20 C21 1.395(7) . ? 
C20 H20 0.9500 . ? 
C21 C22 1.392(7) . ? 
C21 H21 0.9500 . ? 
C23 C28 1.389(7) . ? 
C23 C24 1.402(7) . ? 
C24 C25 1.377(8) . ? 
C24 H24 0.9500 . ? 
C25 C26 1.396(7) . ? 
C26 C27 1.382(7) . ? 
C26 H26 0.9500 . ? 
C27 C28 1.414(7) . ? 
C29 H29A 0.9800 . ? 
C29 H29B 0.9800 . ? 
C29 H29C 0.9800 . ? 
C30 H30A 0.9800 . ? 
C30 H30B 0.9800 . ? 
C30 H30C 0.9800 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C25 O1 C29 116.4(4) . . ? 
C27 O2 C30 117.0(4) . . ? 
C2 C1 C14 113.1(5) . . ? 
C2 C1 H1 123.5 . . ? 
C14 C1 H1 123.5 . . ? 
C1 C2 C3 112.1(5) . . ? 
C1 C2 H2 123.9 . . ? 
C3 C2 H2 123.9 . . ? 
C4 C3 C2 125.7(5) . . ? 
C4 C3 C13 128.5(5) . . ? 
C2 C3 C13 105.8(4) . . ? 
C3 C4 C6 127.1(5) . . ? 
C3 C4 C5 121.0(6) . . ? 
C6 C4 C5 111.9(5) . . ? 
C4 C5 H5A 109.5 . . ? 
C4 C5 H5B 109.5 . . ? 
H5A C5 H5B 109.5 . . ? 
C4 C5 H5C 109.5 . . ? 
H5A C5 H5C 109.5 . . ? 
H5B C5 H5C 109.5 . . ? 
C4 C6 C7 117.6(5) . . ? 
C4 C6 H6A 107.9 . . ? 
C7 C6 H6A 107.9 . . ? 
C4 C6 H6AB 107.9 . . ? 
C7 C6 H6AB 107.9 . . ? 
H6A C6 H6AB 107.2 . . ? 
C8 C7 C6 110.1(5) . . ? 
C8 C7 H7A 109.6 . . ? 
C6 C7 H7A 109.6 . . ? 
C8 C7 H7AB 109.6 . . ? 
C6 C7 H7AB 109.6 . . ? 
H7A C7 H7AB 108.1 . . ? 
C7 C8 C9 124.6(5) . . ? 
C7 C8 C10 118.1(5) . . ? 
C9 C8 C10 60.5(3) . . ? 
C7 C8 H8 114.3 . . ? 
C9 C8 H8 114.3 . . ? 
C10 C8 H8 114.3 . . ? 
C11 C9 C8 120.3(5) . . ? 
C11 C9 C12 112.7(5) . . ? 
C8 C9 C12 115.3(5) . . ? 
C11 C9 C10 123.0(5) . . ? 
C8 C9 C10 59.9(3) . . ? 
C12 C9 C10 116.1(5) . . ? 
C13 C10 C8 119.0(4) . . ? 
C13 C10 C9 123.9(4) . . ? 
C8 C10 C9 59.6(4) . . ? 
C13 C10 H10 114.5 . . ? 
C8 C10 H10 114.5 . . ? 
C9 C10 H10 114.5 . . ? 
C9 C11 H11A 109.5 . . ? 
C9 C11 H11B 109.5 . . ? 
H11A C11 H11B 109.5 . . ? 
C9 C11 H11C 109.5 . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
C9 C12 H12A 109.5 . . ? 
C9 C12 H12B 109.5 . . ? 
H12A C12 H12B 109.5 . . ? 
C9 C12 H12C 109.5 . . ? 
H12A C12 H12C 109.5 . . ? 
H12B C12 H12C 109.5 . . ? 
C10 C13 C3 115.4(4) . . ? 
C10 C13 C14 115.4(4) . . ? 
C3 C13 C14 105.2(4) . . ? 
C10 C13 H13 106.8 . . ? 
C3 C13 H13 106.8 . . ? 
C14 C13 H13 106.8 . . ? 
C1 C14 C15 106.3(5) . . ? 
C1 C14 C16 120.6(4) . . ? 
C15 C14 C16 107.3(4) . . ? 
C1 C14 C13 101.5(4) . . ? 
C15 C14 C13 112.9(4) . . ? 
C16 C14 C13 108.3(4) . . ? 
C14 C15 H15A 109.5 . . ? 
C14 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C14 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 109.5 . . ? 
C28 C16 C22 111.6(4) . . ? 
C28 C16 C14 116.4(4) . . ? 
C22 C16 C14 116.9(4) . . ? 
C28 C16 H16 103.2 . . ? 
C22 C16 H16 103.2 . . ? 
C14 C16 H16 103.2 . . ? 
C22 C17 C18 120.4(5) . . ? 
C22 C17 H17 119.8 . . ? 
C18 C17 H17 119.8 . . ? 
C19 C18 C17 120.0(5) . . ? 
C19 C18 H18 120.0 . . ? 
C17 C18 H18 120.0 . . ? 
C18 C19 C20 119.8(5) . . ? 
C18 C19 H19 120.1 . . ? 
C20 C19 H19 120.1 . . ? 
C19 C20 C21 119.6(5) . . ? 
C19 C20 H20 120.2 . . ? 
C21 C20 H20 120.2 . . ? 
C22 C21 C20 121.0(5) . . ? 
C22 C21 H21 119.5 . . ? 
C20 C21 H21 119.5 . . ? 
C17 C22 C21 119.1(4) . . ? 
C17 C22 C16 124.5(4) . . ? 
C21 C22 C16 116.4(4) . . ? 
C28 C23 C24 124.6(5) . . ? 
C28 C23 Br1 121.7(4) . . ? 
C24 C23 Br1 113.7(4) . . ? 
C25 C24 C23 118.0(5) . . ? 
C25 C24 H24 121.0 . . ? 
C23 C24 H24 121.0 . . ? 
O1 C25 C24 124.5(5) . . ? 
O1 C25 C26 115.0(5) . . ? 
C24 C25 C26 120.5(5) . . ? 
C27 C26 C25 119.6(5) . . ? 
C27 C26 H26 120.2 . . ? 
C25 C26 H26 120.2 . . ? 
O2 C27 C26 122.0(5) . . ? 
O2 C27 C28 115.2(4) . . ? 
C26 C27 C28 122.8(5) . . ? 
C23 C28 C27 114.5(5) . . ? 
C23 C28 C16 122.4(4) . . ? 
C27 C28 C16 123.1(4) . . ? 
O1 C29 H29A 109.5 . . ? 
O1 C29 H29B 109.5 . . ? 
H29A C29 H29B 109.5 . . ? 
O1 C29 H29C 109.5 . . ? 
H29A C29 H29C 109.5 . . ? 
H29B C29 H29C 109.5 . . ? 
O2 C30 H30A 109.5 . . ? 
O2 C30 H30B 109.5 . . ? 
H30A C30 H30B 109.5 . . ? 
O2 C30 H30C 109.5 . . ? 
H30A C30 H30C 109.5 . . ? 
H30B C30 H30C 109.5 . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C14 C1 C2 C3 -5.1(7) . . . . ? 
C1 C2 C3 C4 177.3(5) . . . . ? 
C1 C2 C3 C13 -5.2(6) . . . . ? 
C2 C3 C4 C6 174.6(6) . . . . ? 
C13 C3 C4 C6 -2.3(9) . . . . ? 
C2 C3 C4 C5 -3.9(8) . . . . ? 
C13 C3 C4 C5 179.3(5) . . . . ? 
C3 C4 C6 C7 -14.5(9) . . . . ? 
C5 C4 C6 C7 164.0(5) . . . . ? 
C4 C6 C7 C8 71.3(7) . . . . ? 
C6 C7 C8 C9 -144.5(6) . . . . ? 
C6 C7 C8 C10 -72.5(6) . . . . ? 
C7 C8 C9 C11 -7.5(8) . . . . ? 
C10 C8 C9 C11 -113.0(6) . . . . ? 
C7 C8 C9 C12 -147.8(5) . . . . ? 
C10 C8 C9 C12 106.7(5) . . . . ? 
C7 C8 C9 C10 105.5(6) . . . . ? 
C7 C8 C10 C13 -1.5(7) . . . . ? 
C9 C8 C10 C13 114.4(5) . . . . ? 
C7 C8 C10 C9 -116.0(5) . . . . ? 
C11 C9 C10 C13 2.2(8) . . . . ? 
C8 C9 C10 C13 -106.4(5) . . . . ? 
C12 C9 C10 C13 148.2(5) . . . . ? 
C11 C9 C10 C8 108.6(6) . . . . ? 
C12 C9 C10 C8 -105.4(5) . . . . ? 
C8 C10 C13 C3 60.1(6) . . . . ? 
C9 C10 C13 C3 131.1(5) . . . . ? 
C8 C10 C13 C14 -176.8(4) . . . . ? 
C9 C10 C13 C14 -105.8(5) . . . . ? 
C4 C3 C13 C10 -41.6(8) . . . . ? 
C2 C3 C13 C10 141.1(5) . . . . ? 
C4 C3 C13 C14 -170.0(5) . . . . ? 
C2 C3 C13 C14 12.7(5) . . . . ? 
C2 C1 C14 C15 -105.6(6) . . . . ? 
C2 C1 C14 C16 132.2(5) . . . . ? 
C2 C1 C14 C13 12.7(6) . . . . ? 
C10 C13 C14 C1 -143.1(4) . . . . ? 
C3 C13 C14 C1 -14.7(5) . . . . ? 
C10 C13 C14 C15 -29.7(6) . . . . ? 
C3 C13 C14 C15 98.7(5) . . . . ? 
C10 C13 C14 C16 89.0(5) . . . . ? 
C3 C13 C14 C16 -142.6(4) . . . . ? 
C1 C14 C16 C28 77.0(6) . . . . ? 
C15 C14 C16 C28 -44.7(6) . . . . ? 
C13 C14 C16 C28 -166.9(4) . . . . ? 
C1 C14 C16 C22 -58.5(7) . . . . ? 
C15 C14 C16 C22 179.8(4) . . . . ? 
C13 C14 C16 C22 57.6(5) . . . . ? 
C22 C17 C18 C19 0.3(8) . . . . ? 
C17 C18 C19 C20 -0.8(8) . . . . ? 
C18 C19 C20 C21 0.3(8) . . . . ? 
C19 C20 C21 C22 0.8(7) . . . . ? 
C18 C17 C22 C21 0.8(7) . . . . ? 
C18 C17 C22 C16 -177.7(5) . . . . ? 
C20 C21 C22 C17 -1.4(7) . . . . ? 
C20 C21 C22 C16 177.3(4) . . . . ? 
C28 C16 C22 C17 -102.0(5) . . . . ? 
C14 C16 C22 C17 35.5(7) . . . . ? 
C28 C16 C22 C21 79.4(5) . . . . ? 
C14 C16 C22 C21 -143.1(5) . . . . ? 
C28 C23 C24 C25 -0.5(7) . . . . ? 
Br1 C23 C24 C25 -179.7(4) . . . . ? 
C29 O1 C25 C24 -4.6(7) . . . . ? 
C29 O1 C25 C26 175.7(4) . . . . ? 
C23 C24 C25 O1 178.9(4) . . . . ? 
C23 C24 C25 C26 -1.4(7) . . . . ? 
O1 C25 C26 C27 -179.4(4) . . . . ? 
C24 C25 C26 C27 0.8(7) . . . . ? 
C30 O2 C27 C26 -5.6(7) . . . . ? 
C30 O2 C27 C28 174.6(5) . . . . ? 
C25 C26 C27 O2 -178.1(4) . . . . ? 
C25 C26 C27 C28 1.7(7) . . . . ? 
C24 C23 C28 C27 2.8(7) . . . . ? 
Br1 C23 C28 C27 -178.0(3) . . . . ? 
C24 C23 C28 C16 -178.3(4) . . . . ? 
Br1 C23 C28 C16 0.8(6) . . . . ? 
O2 C27 C28 C23 176.4(4) . . . . ? 
C26 C27 C28 C23 -3.4(7) . . . . ? 
O2 C27 C28 C16 -2.4(6) . . . . ? 
C26 C27 C28 C16 177.8(4) . . . . ? 
C22 C16 C28 C23 -110.4(5) . . . . ? 
C14 C16 C28 C23 111.8(5) . . . . ? 
C22 C16 C28 C27 68.3(6) . . . . ? 
C14 C16 C28 C27 -69.4(6) . . . . ? 
  
_refine_diff_density_max    0.702 
_refine_diff_density_min   -0.519 
_refine_diff_density_rms    0.108 
  
  
  

data_chai216
_audit_creation_date               2023-07-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number       '2019/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C30 H35 Br O3'
_chemical_formula_sum              'C30 H35 Br O3'
_chemical_formula_weight           523.49
_chemical_absolute_configuration   ad
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br' 'Br' -0.6763 1.2805
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     8.5187(5)
_cell_length_b                     27.1207(15)
_cell_length_c                     11.3492(6)
_cell_angle_alpha                  90
_cell_angle_beta                   93.832(2)
_cell_angle_gamma                  90
_cell_volume                       2616.2(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9109
_cell_measurement_temperature      100.00
_cell_measurement_theta_max        70.37
_cell_measurement_theta_min        3.26
_shelx_estimated_absorpt_T_max     0.897
_shelx_estimated_absorpt_T_min     0.675
_exptl_absorpt_coefficient_mu      2.359
_exptl_absorpt_correction_T_max    0.7533
_exptl_absorpt_correction_T_min    0.5877
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1043 before and 0.0822 after correction.
The Ratio of minimum to maximum transmission is 0.7802.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.329
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1096
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 -3.00 -2.00 1.00 0.0550
 -2.00 -3.00 3.00 0.0470
 -1.00 1.00 -1.00 0.0330
 0.00 1.00 1.00 0.0230
 0.00 -1.00 -1.00 0.0140
 0.00 -1.00 0.00 0.0270
 0.00 1.00 0.00 0.0400
 1.00 -1.00 1.00 0.0720
 3.00 2.00 -1.00 0.0880
 3.00 -3.00 -2.00 0.0770

_exptl_crystal_size_max            0.181
_exptl_crystal_size_mid            0.099
_exptl_crystal_size_min            0.047
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0473
_diffrn_reflns_av_unetI/netI       0.0285
_diffrn_reflns_Laue_measured_fraction_full  0.996
_diffrn_reflns_Laue_measured_fraction_max  0.991
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         33
_diffrn_reflns_limit_k_min         -32
_diffrn_reflns_limit_l_max         13
_diffrn_reflns_limit_l_min         -13
_diffrn_reflns_number              51679
_diffrn_reflns_point_group_measured_fraction_full  0.984
_diffrn_reflns_point_group_measured_fraction_max  0.969
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           70.374
_diffrn_reflns_theta_min           3.259
_diffrn_ambient_temperature        100.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.996
_diffrn_measured_fraction_theta_max  0.991
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     ?
_diffrn_source_current             1.2
_diffrn_source_power               0.06
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.914
_reflns_Friedel_fraction_full      0.970
_reflns_Friedel_fraction_max       0.947
_reflns_number_gt                  9529
_reflns_number_total               9670
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.869
_refine_diff_density_min           -0.522
_refine_diff_density_rms           0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 4411 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.000(11)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.026
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       625
_refine_ls_number_reflns           9670
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0446
_refine_ls_R_factor_gt             0.0437
_refine_ls_restrained_S_all        1.026
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0613P)²+3.6378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1139
_refine_ls_wR_factor_ref           0.1149
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6), C9(H9), C10(H10), C11(H11), C31(H31), C36(H36), C39(H39),
 C40(H40), C41(H41)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C37(H37A,H37B), C38(H38A,H38B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C18(H18), C20(H20), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29),
 C34(H34), C48(H48), C50(H50), C55(H55), C56(H56), C57(H57), C58(H58), C59(H59)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C42(H42A,H42B,H42C), C44(H44A,
 H44B,H44C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C53(H53A,H53B,H53C),
 C54(H54A,H54B,H54C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Br1 Br -0.00999(7) 0.31674(2) 0.40145(6) 0.04115(17) Uani 1 1 d . . . . .
 O1 O 0.5852(5) 0.41289(15) 0.1479(4) 0.0374(9) Uani 1 1 d . . . . .
 O2 O 0.0625(6) 0.47685(17) 0.6364(4) 0.0421(10) Uani 1 1 d . . . . .
 O3 O 0.3362(5) 0.46377(13) 0.2779(3) 0.0311(8) Uani 1 1 d . . . . .
 C1 C 0.2286(6) 0.3700(2) 0.2283(5) 0.0299(11) Uani 1 1 d . . . . .
 H1 H 0.168135 0.338582 0.233887 0.036 Uiso 1 1 calc R U . . .
 C2 C 0.4049(6) 0.35171(19) 0.2243(5) 0.0290(11) Uani 1 1 d . . . . .
 C3 C 0.5331(6) 0.3921(2) 0.2321(5) 0.0329(12) Uani 1 1 d . . . . .
 C4 C 0.5929(7) 0.3965(2) 0.3558(5) 0.0379(13) Uani 1 1 d . . . . .
 H4 H 0.660793 0.421924 0.386143 0.046 Uiso 1 1 calc R U . . .
 C5 C 0.5385(7) 0.3597(2) 0.4196(5) 0.0360(13) Uani 1 1 d . . . . .
 C6 C 0.5772(11) 0.3495(3) 0.5496(6) 0.0543(18) Uani 1 1 d . . . . .
 H6 H 0.690825 0.339862 0.553976 0.065 Uiso 1 1 calc R U . . .
 C7 C 0.4988(15) 0.3067(4) 0.5944(7) 0.084(3) Uani 1 1 d . . . . .
 H7A H 0.384636 0.313234 0.580736 0.101 Uiso 1 1 calc R U . . .
 H7B H 0.521645 0.307178 0.681089 0.101 Uiso 1 1 calc R U . . .
 C8 C 0.5221(10) 0.2557(2) 0.5575(6) 0.0472(17) Uani 1 1 d . . . . .
 H8A H 0.420315 0.238431 0.561618 0.057 Uiso 1 1 calc R U . . .
 H8B H 0.596664 0.240263 0.617172 0.057 Uiso 1 1 calc R U . . .
 C9 C 0.5815(8) 0.2450(2) 0.4371(5) 0.0387(13) Uani 1 1 d . . . . .
 H9 H 0.691545 0.231944 0.441382 0.046 Uiso 1 1 calc R U . . .
 C10 C 0.5445(7) 0.2778(2) 0.3317(5) 0.0317(12) Uani 1 1 d . . . . .
 H10 H 0.634514 0.282537 0.280630 0.038 Uiso 1 1 calc R U . . .
 C11 C 0.4438(6) 0.3231(2) 0.3431(5) 0.0308(11) Uani 1 1 d . . . . .
 H11 H 0.344456 0.314355 0.380520 0.037 Uiso 1 1 calc R U . . .
 C12 C 0.5748(12) 0.3966(3) 0.6194(7) 0.062(2) Uani 1 1 d . . . . .
 H12A H 0.647689 0.420309 0.587549 0.093 Uiso 1 1 calc R U . . .
 H12B H 0.607107 0.389776 0.702287 0.093 Uiso 1 1 calc R U . . .
 H12C H 0.468189 0.410277 0.613714 0.093 Uiso 1 1 calc R U . . .
 C13 C 0.4810(7) 0.2256(2) 0.3318(5) 0.0355(12) Uani 1 1 d . . . . .
 C14 C 0.3092(8) 0.2163(2) 0.3450(6) 0.0430(14) Uani 1 1 d . . . . .
 H14A H 0.271080 0.239043 0.403934 0.065 Uiso 1 1 calc R U . . .
 H14B H 0.294330 0.182276 0.370774 0.065 Uiso 1 1 calc R U . . .
 H14C H 0.250193 0.221710 0.269008 0.065 Uiso 1 1 calc R U . . .
 C15 C 0.5530(9) 0.1897(3) 0.2497(5) 0.0480(15) Uani 1 1 d . . . . .
 H15A H 0.512790 0.196330 0.168304 0.072 Uiso 1 1 calc R U . . .
 H15B H 0.525425 0.155965 0.271357 0.072 Uiso 1 1 calc R U . . .
 H15C H 0.667690 0.193447 0.255937 0.072 Uiso 1 1 calc R U . . .
 C16 C 0.4181(7) 0.3209(2) 0.1125(5) 0.0371(12) Uani 1 1 d . . . . .
 H16A H 0.525578 0.308216 0.110346 0.056 Uiso 1 1 calc R U . . .
 H16B H 0.393172 0.341558 0.042857 0.056 Uiso 1 1 calc R U . . .
 H16C H 0.344070 0.293270 0.112617 0.056 Uiso 1 1 calc R U . . .
 C17 C 0.0861(7) 0.3804(2) 0.4199(5) 0.0354(12) Uani 1 1 d . . . . .
 C18 C 0.0453(7) 0.4064(2) 0.5183(5) 0.0356(13) Uani 1 1 d . . . . .
 H18 H -0.025322 0.392700 0.570839 0.043 Uiso 1 1 calc R U . . .
 C19 C 0.1106(7) 0.4533(2) 0.5388(5) 0.0342(12) Uani 1 1 d . . . . .
 C20 C 0.2116(7) 0.4730(2) 0.4610(5) 0.0321(11) Uani 1 1 d . . . . .
 H20 H 0.255847 0.504842 0.474610 0.039 Uiso 1 1 calc R U . . .
 C21 C 0.2477(6) 0.44585(19) 0.3624(5) 0.0282(10) Uani 1 1 d . . . . .
 C22 C 0.1889(6) 0.3979(2) 0.3386(5) 0.0288(11) Uani 1 1 d . . . . .
 C23 C 0.1313(8) 0.5246(2) 0.6626(5) 0.0414(13) Uani 1 1 d . . . . .
 H23A H 0.102312 0.547407 0.597853 0.062 Uiso 1 1 calc R U . . .
 H23B H 0.246073 0.521475 0.671783 0.062 Uiso 1 1 calc R U . . .
 H23C H 0.092171 0.537237 0.736034 0.062 Uiso 1 1 calc R U . . .
 C24 C 0.4101(7) 0.5109(2) 0.2975(5) 0.0362(12) Uani 1 1 d . . . . .
 H24A H 0.465882 0.520144 0.227961 0.054 Uiso 1 1 calc R U . . .
 H24B H 0.484998 0.509090 0.366690 0.054 Uiso 1 1 calc R U . . .
 H24C H 0.329708 0.535782 0.311054 0.054 Uiso 1 1 calc R U . . .
 C25 C 0.2260(7) 0.4271(2) 0.0442(5) 0.0372(12) Uani 1 1 d . . . . .
 H25 H 0.333064 0.435579 0.062502 0.045 Uiso 1 1 calc R U . . .
 C26 C 0.1456(7) 0.4473(2) -0.0554(5) 0.0424(14) Uani 1 1 d . . . . .
 H26 H 0.198680 0.469200 -0.104641 0.051 Uiso 1 1 calc R U . . .
 C27 C -0.0093(7) 0.4359(2) -0.0829(5) 0.0381(13) Uani 1 1 d . . . . .
 H27 H -0.063521 0.449668 -0.151011 0.046 Uiso 1 1 calc R U . . .
 C28 C -0.0856(7) 0.4043(2) -0.0108(5) 0.0354(12) Uani 1 1 d . . . . .
 H28 H -0.193161 0.396459 -0.028961 0.042 Uiso 1 1 calc R U . . .
 C29 C -0.0066(6) 0.3838(2) 0.0879(5) 0.0297(12) Uani 1 1 d . . . . .
 H29 H -0.060862 0.362032 0.136504 0.036 Uiso 1 1 calc R U . . .
 C30 C 0.1510(7) 0.3947(2) 0.1172(5) 0.0299(11) Uani 1 1 d . . . . .
 Br2 Br 0.47055(7) 0.68748(2) 0.11288(5) 0.03883(16) Uani 1 1 d . . . . .
 O4 O 1.1132(5) 0.59218(15) 0.3644(3) 0.0362(9) Uani 1 1 d . . . . .
 O5 O 0.4786(5) 0.52436(16) -0.1125(3) 0.0367(9) Uani 1 1 d . . . . .
 O6 O 0.8357(4) 0.53968(13) 0.2359(3) 0.0299(8) Uani 1 1 d . . . . .
 C31 C 0.7407(6) 0.63401(19) 0.2838(4) 0.0260(10) Uani 1 1 d . . . . .
 H31 H 0.678977 0.665385 0.278409 0.031 Uiso 1 1 calc R U . . .
 C32 C 0.9171(6) 0.65238(19) 0.2832(5) 0.0277(11) Uani 1 1 d . . . . .
 C33 C 1.0454(6) 0.6123(2) 0.2781(5) 0.0318(12) Uani 1 1 d . . . . .
 C34 C 1.0792(7) 0.6052(2) 0.1540(5) 0.0352(12) Uani 1 1 d . . . . .
 H34 H 1.140205 0.578992 0.125438 0.042 Uiso 1 1 calc R U . . .
 C35 C 1.0121(7) 0.6407(2) 0.0873(5) 0.0357(13) Uani 1 1 d . . . . .
 C36 C 1.0134(11) 0.6441(3) -0.0476(6) 0.0523(18) Uani 1 1 d . . . . .
 H36 H 1.094277 0.619875 -0.070961 0.063 Uiso 1 1 calc R U . . .
 C37 C 1.0610(9) 0.6936(3) -0.0969(5) 0.0461(16) Uani 1 1 d . . . . .
 H37A H 1.041748 0.692414 -0.183886 0.055 Uiso 1 1 calc R U . . .
 H37B H 1.175726 0.697603 -0.079734 0.055 Uiso 1 1 calc R U . . .
 C38 C 0.9799(9) 0.7399(3) -0.0525(6) 0.0420(15) Uani 1 1 d . . . . .
 H38A H 0.985813 0.766923 -0.110636 0.050 Uiso 1 1 calc R U . . .
 H38B H 0.867633 0.732870 -0.041948 0.050 Uiso 1 1 calc R U . . .
 C39 C 1.0627(9) 0.7548(2) 0.0641(5) 0.0453(15) Uani 1 1 d . . . . .
 H39 H 1.173147 0.766401 0.057278 0.054 Uiso 1 1 calc R U . . .
 C40 C 1.0417(7) 0.7237(2) 0.1715(5) 0.0334(12) Uani 1 1 d . . . . .
 H40 H 1.140920 0.718465 0.222176 0.040 Uiso 1 1 calc R U . . .
 C41 C 0.9354(6) 0.6789(2) 0.1628(4) 0.0291(11) Uani 1 1 d . . . . .
 H41 H 0.829681 0.688200 0.125768 0.035 Uiso 1 1 calc R U . . .
 C42 C 0.8649(10) 0.6276(3) -0.1039(7) 0.0588(19) Uani 1 1 d . . . . .
 H42A H 0.781078 0.650275 -0.084082 0.088 Uiso 1 1 calc R U . . .
 H42B H 0.841223 0.594398 -0.076038 0.088 Uiso 1 1 calc R U . . .
 H42C H 0.872054 0.627000 -0.189734 0.088 Uiso 1 1 calc R U . . .
 C43 C 0.9852(10) 0.7761(2) 0.1686(6) 0.0492(18) Uani 1 1 d . . . . .
 C44 C 0.8121(12) 0.7869(3) 0.1618(6) 0.071(3) Uani 1 1 d . . . . .
 H44A H 0.756592 0.762609 0.110485 0.107 Uiso 1 1 calc R U . . .
 H44B H 0.793381 0.820034 0.129457 0.107 Uiso 1 1 calc R U . . .
 H44C H 0.773401 0.785092 0.241092 0.107 Uiso 1 1 calc R U . . .
 C45 C 1.0875(14) 0.8111(3) 0.2446(6) 0.078(3) Uani 1 1 d . . . . .
 H45A H 1.065025 0.806997 0.327574 0.117 Uiso 1 1 calc R U . . .
 H45B H 1.065086 0.845140 0.219988 0.117 Uiso 1 1 calc R U . . .
 H45C H 1.198647 0.803703 0.235248 0.117 Uiso 1 1 calc R U . . .
 C46 C 0.9508(7) 0.6847(2) 0.3923(4) 0.0327(11) Uani 1 1 d . . . . .
 H46A H 0.881138 0.713469 0.387712 0.049 Uiso 1 1 calc R U . . .
 H46B H 1.060599 0.695623 0.395764 0.049 Uiso 1 1 calc R U . . .
 H46C H 0.932160 0.665625 0.463430 0.049 Uiso 1 1 calc R U . . .
 C47 C 0.5566(7) 0.6232(2) 0.0965(5) 0.0294(11) Uani 1 1 d . . . . .
 C48 C 0.4906(6) 0.5959(2) 0.0018(5) 0.0314(11) Uani 1 1 d . . . . .
 H48 H 0.407481 0.609113 -0.048662 0.038 Uiso 1 1 calc R U . . .
 C49 C 0.5491(6) 0.5490(2) -0.0171(5) 0.0305(11) Uani 1 1 d . . . . .
 C50 C 0.6677(6) 0.52924(19) 0.0577(5) 0.0282(10) Uani 1 1 d . . . . .
 H50 H 0.707699 0.497196 0.044035 0.034 Uiso 1 1 calc R U . . .
 C51 C 0.7274(6) 0.55727(18) 0.1535(4) 0.0249(10) Uani 1 1 d . . . . .
 C52 C 0.6774(6) 0.60545(19) 0.1757(4) 0.0254(10) Uani 1 1 d . . . . .
 C53 C 0.5423(8) 0.4777(2) -0.1410(6) 0.0410(14) Uani 1 1 d . . . . .
 H53A H 0.476903 0.462678 -0.205699 0.062 Uiso 1 1 calc R U . . .
 H53B H 0.544202 0.456152 -0.071557 0.062 Uiso 1 1 calc R U . . .
 H53C H 0.649648 0.482048 -0.165351 0.062 Uiso 1 1 calc R U . . .
 C54 C 0.9020(7) 0.4919(2) 0.2189(6) 0.0376(13) Uani 1 1 d . . . . .
 H54A H 0.964748 0.492496 0.149618 0.056 Uiso 1 1 calc R U . . .
 H54B H 0.817184 0.467609 0.206504 0.056 Uiso 1 1 calc R U . . .
 H54C H 0.969337 0.482764 0.288883 0.056 Uiso 1 1 calc R U . . .
 C55 C 0.7790(7) 0.5790(2) 0.4712(5) 0.0350(12) Uani 1 1 d . . . . .
 H55 H 0.884388 0.571828 0.454424 0.042 Uiso 1 1 calc R U . . .
 C56 C 0.7168(7) 0.5586(2) 0.5711(5) 0.0388(13) Uani 1 1 d . . . . .
 H56 H 0.780613 0.537787 0.621756 0.047 Uiso 1 1 calc R U . . .
 C57 C 0.5639(8) 0.5682(2) 0.5971(5) 0.0361(13) Uani 1 1 d . . . . .
 H57 H 0.523088 0.554487 0.665759 0.043 Uiso 1 1 calc R U . . .
 C58 C 0.4695(7) 0.5982(2) 0.5214(5) 0.0337(12) Uani 1 1 d . . . . .
 H58 H 0.363300 0.604629 0.537249 0.040 Uiso 1 1 calc R U . . .
 C59 C 0.5325(7) 0.6185(2) 0.4229(5) 0.0286(11) Uani 1 1 d . . . . .
 H59 H 0.467876 0.639119 0.372346 0.034 Uiso 1 1 calc R U . . .
 C60 C 0.6865(6) 0.60999(19) 0.3954(4) 0.0267(10) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Br1 C17 1.917(6) . ?
 O1 C3 1.218(7) . ?
 O2 C19 1.364(7) . ?
 O2 C23 1.444(8) . ?
 O3 C21 1.350(6) . ?
 O3 C24 1.436(6) . ?
 C1 H1 1.0000 . ?
 C1 C2 1.585(7) . ?
 C1 C22 1.519(7) . ?
 C1 C30 1.537(7) . ?
 C2 C3 1.545(8) . ?
 C2 C11 1.572(7) . ?
 C2 C16 1.530(8) . ?
 C3 C4 1.465(8) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.335(9) . ?
 C5 C6 1.516(9) . ?
 C5 C11 1.515(8) . ?
 C6 H6 1.0000 . ?
 C6 C7 1.447(12) . ?
 C6 C12 1.503(10) . ?
 C7 H7A 0.9900 . ?
 C7 H7B 0.9900 . ?
 C7 C8 1.463(12) . ?
 C8 H8A 0.9900 . ?
 C8 H8B 0.9900 . ?
 C8 C9 1.516(9) . ?
 C9 H9 1.0000 . ?
 C9 C10 1.508(8) . ?
 C9 C13 1.518(9) . ?
 C10 H10 1.0000 . ?
 C10 C11 1.509(7) . ?
 C10 C13 1.516(8) . ?
 C11 H11 1.0000 . ?
 C12 H12A 0.9800 . ?
 C12 H12B 0.9800 . ?
 C12 H12C 0.9800 . ?
 C13 C14 1.502(9) . ?
 C13 C15 1.506(8) . ?
 C14 H14A 0.9800 . ?
 C14 H14B 0.9800 . ?
 C14 H14C 0.9800 . ?
 C15 H15A 0.9800 . ?
 C15 H15B 0.9800 . ?
 C15 H15C 0.9800 . ?
 C16 H16A 0.9800 . ?
 C16 H16B 0.9800 . ?
 C16 H16C 0.9800 . ?
 C17 C18 1.384(8) . ?
 C17 C22 1.397(8) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.401(8) . ?
 C19 C20 1.382(8) . ?
 C20 H20 0.9500 . ?
 C20 C21 1.392(8) . ?
 C21 C22 1.414(8) . ?
 C23 H23A 0.9800 . ?
 C23 H23B 0.9800 . ?
 C23 H23C 0.9800 . ?
 C24 H24A 0.9800 . ?
 C24 H24B 0.9800 . ?
 C24 H24C 0.9800 . ?
 C25 H25 0.9500 . ?
 C25 C26 1.394(8) . ?
 C25 C30 1.393(8) . ?
 C26 H26 0.9500 . ?
 C26 C27 1.371(9) . ?
 C27 H27 0.9500 . ?
 C27 C28 1.378(9) . ?
 C28 H28 0.9500 . ?
 C28 C29 1.383(8) . ?
 C29 H29 0.9500 . ?
 C29 C30 1.392(8) . ?
 Br2 C47 1.906(6) . ?
 O4 C33 1.230(7) . ?
 O5 C49 1.376(7) . ?
 O5 C53 1.423(8) . ?
 O6 C51 1.355(6) . ?
 O6 C54 1.433(7) . ?
 C31 H31 1.0000 . ?
 C31 C32 1.583(7) . ?
 C31 C52 1.520(7) . ?
 C31 C60 1.523(7) . ?
 C32 C33 1.547(8) . ?
 C32 C41 1.562(7) . ?
 C32 C46 1.528(7) . ?
 C33 C34 1.469(8) . ?
 C34 H34 0.9500 . ?
 C34 C35 1.331(9) . ?
 C35 C36 1.534(9) . ?
 C35 C41 1.519(8) . ?
 C36 H36 1.0000 . ?
 C36 C37 1.522(10) . ?
 C36 C42 1.449(12) . ?
 C37 H37A 0.9900 . ?
 C37 H37B 0.9900 . ?
 C37 C38 1.533(10) . ?
 C38 H38A 0.9900 . ?
 C38 H38B 0.9900 . ?
 C38 C39 1.513(9) . ?
 C39 H39 1.0000 . ?
 C39 C40 1.503(8) . ?
 C39 C43 1.511(10) . ?
 C40 H40 1.0000 . ?
 C40 C41 1.513(7) . ?
 C40 C43 1.501(9) . ?
 C41 H41 1.0000 . ?
 C42 H42A 0.9800 . ?
 C42 H42B 0.9800 . ?
 C42 H42C 0.9800 . ?
 C43 C44 1.500(13) . ?
 C43 C45 1.518(11) . ?
 C44 H44A 0.9800 . ?
 C44 H44B 0.9800 . ?
 C44 H44C 0.9800 . ?
 C45 H45A 0.9800 . ?
 C45 H45B 0.9800 . ?
 C45 H45C 0.9800 . ?
 C46 H46A 0.9800 . ?
 C46 H46B 0.9800 . ?
 C46 H46C 0.9800 . ?
 C47 C48 1.391(8) . ?
 C47 C52 1.405(7) . ?
 C48 H48 0.9500 . ?
 C48 C49 1.389(8) . ?
 C49 C50 1.383(8) . ?
 C50 H50 0.9500 . ?
 C50 C51 1.395(7) . ?
 C51 C52 1.402(7) . ?
 C53 H53A 0.9800 . ?
 C53 H53B 0.9800 . ?
 C53 H53C 0.9800 . ?
 C54 H54A 0.9800 . ?
 C54 H54B 0.9800 . ?
 C54 H54C 0.9800 . ?
 C55 H55 0.9500 . ?
 C55 C56 1.397(8) . ?
 C55 C60 1.407(7) . ?
 C56 H56 0.9500 . ?
 C56 C57 1.379(9) . ?
 C57 H57 0.9500 . ?
 C57 C58 1.399(9) . ?
 C58 H58 0.9500 . ?
 C58 C59 1.386(8) . ?
 C59 H59 0.9500 . ?
 C59 C60 1.388(8) . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C19 O2 C23 116.6(5) . . ?
 C21 O3 C24 118.1(4) . . ?
 C2 C1 H1 103.2 . . ?
 C22 C1 H1 103.2 . . ?
 C22 C1 C2 116.2(4) . . ?
 C22 C1 C30 110.7(4) . . ?
 C30 C1 H1 103.2 . . ?
 C30 C1 C2 118.0(4) . . ?
 C3 C2 C1 116.4(4) . . ?
 C3 C2 C11 101.1(4) . . ?
 C11 C2 C1 106.0(4) . . ?
 C16 C2 C1 108.5(4) . . ?
 C16 C2 C3 110.1(4) . . ?
 C16 C2 C11 114.8(4) . . ?
 O1 C3 C2 125.2(5) . . ?
 O1 C3 C4 126.3(5) . . ?
 C4 C3 C2 108.2(5) . . ?
 C3 C4 H4 124.8 . . ?
 C5 C4 C3 110.4(5) . . ?
 C5 C4 H4 124.8 . . ?
 C4 C5 C6 127.2(6) . . ?
 C4 C5 C11 111.7(5) . . ?
 C11 C5 C6 120.8(5) . . ?
 C5 C6 H6 104.0 . . ?
 C7 C6 C5 114.4(7) . . ?
 C7 C6 H6 104.0 . . ?
 C7 C6 C12 118.2(7) . . ?
 C12 C6 C5 110.3(6) . . ?
 C12 C6 H6 104.0 . . ?
 C6 C7 H7A 105.9 . . ?
 C6 C7 H7B 105.9 . . ?
 C6 C7 C8 125.6(8) . . ?
 H7A C7 H7B 106.2 . . ?
 C8 C7 H7A 105.9 . . ?
 C8 C7 H7B 105.9 . . ?
 C7 C8 H8A 107.3 . . ?
 C7 C8 H8B 107.3 . . ?
 C7 C8 C9 120.0(6) . . ?
 H8A C8 H8B 106.9 . . ?
 C9 C8 H8A 107.3 . . ?
 C9 C8 H8B 107.3 . . ?
 C8 C9 H9 113.1 . . ?
 C8 C9 C13 124.9(6) . . ?
 C10 C9 C8 122.5(5) . . ?
 C10 C9 H9 113.1 . . ?
 C10 C9 C13 60.1(4) . . ?
 C13 C9 H9 113.1 . . ?
 C9 C10 H10 114.1 . . ?
 C9 C10 C11 120.1(5) . . ?
 C9 C10 C13 60.2(4) . . ?
 C11 C10 H10 114.1 . . ?
 C11 C10 C13 123.8(5) . . ?
 C13 C10 H10 114.1 . . ?
 C2 C11 H11 110.2 . . ?
 C5 C11 C2 104.0(4) . . ?
 C5 C11 H11 110.2 . . ?
 C10 C11 C2 114.6(4) . . ?
 C10 C11 C5 107.3(4) . . ?
 C10 C11 H11 110.2 . . ?
 C6 C12 H12A 109.5 . . ?
 C6 C12 H12B 109.5 . . ?
 C6 C12 H12C 109.5 . . ?
 H12A C12 H12B 109.5 . . ?
 H12A C12 H12C 109.5 . . ?
 H12B C12 H12C 109.5 . . ?
 C10 C13 C9 59.6(4) . . ?
 C14 C13 C9 118.8(5) . . ?
 C14 C13 C10 120.4(5) . . ?
 C14 C13 C15 113.2(6) . . ?
 C15 C13 C9 118.7(6) . . ?
 C15 C13 C10 116.3(5) . . ?
 C13 C14 H14A 109.5 . . ?
 C13 C14 H14B 109.5 . . ?
 C13 C14 H14C 109.5 . . ?
 H14A C14 H14B 109.5 . . ?
 H14A C14 H14C 109.5 . . ?
 H14B C14 H14C 109.5 . . ?
 C13 C15 H15A 109.5 . . ?
 C13 C15 H15B 109.5 . . ?
 C13 C15 H15C 109.5 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 109.5 . . ?
 C2 C16 H16A 109.5 . . ?
 C2 C16 H16B 109.5 . . ?
 C2 C16 H16C 109.5 . . ?
 H16A C16 H16B 109.5 . . ?
 H16A C16 H16C 109.5 . . ?
 H16B C16 H16C 109.5 . . ?
 C18 C17 Br1 114.7(4) . . ?
 C18 C17 C22 124.3(6) . . ?
 C22 C17 Br1 121.0(4) . . ?
 C17 C18 H18 120.7 . . ?
 C17 C18 C19 118.5(5) . . ?
 C19 C18 H18 120.7 . . ?
 O2 C19 C18 115.0(5) . . ?
 O2 C19 C20 124.8(5) . . ?
 C20 C19 C18 120.2(5) . . ?
 C19 C20 H20 120.3 . . ?
 C19 C20 C21 119.3(5) . . ?
 C21 C20 H20 120.3 . . ?
 O3 C21 C20 123.0(5) . . ?
 O3 C21 C22 113.8(5) . . ?
 C20 C21 C22 123.1(5) . . ?
 C17 C22 C1 124.1(5) . . ?
 C17 C22 C21 114.5(5) . . ?
 C21 C22 C1 121.3(4) . . ?
 O2 C23 H23A 109.5 . . ?
 O2 C23 H23B 109.5 . . ?
 O2 C23 H23C 109.5 . . ?
 H23A C23 H23B 109.5 . . ?
 H23A C23 H23C 109.5 . . ?
 H23B C23 H23C 109.5 . . ?
 O3 C24 H24A 109.5 . . ?
 O3 C24 H24B 109.5 . . ?
 O3 C24 H24C 109.5 . . ?
 H24A C24 H24B 109.5 . . ?
 H24A C24 H24C 109.5 . . ?
 H24B C24 H24C 109.5 . . ?
 C26 C25 H25 119.6 . . ?
 C30 C25 H25 119.6 . . ?
 C30 C25 C26 120.7(6) . . ?
 C25 C26 H26 119.7 . . ?
 C27 C26 C25 120.6(6) . . ?
 C27 C26 H26 119.7 . . ?
 C26 C27 H27 120.3 . . ?
 C26 C27 C28 119.3(5) . . ?
 C28 C27 H27 120.3 . . ?
 C27 C28 H28 119.8 . . ?
 C27 C28 C29 120.5(6) . . ?
 C29 C28 H28 119.8 . . ?
 C28 C29 H29 119.4 . . ?
 C28 C29 C30 121.2(5) . . ?
 C30 C29 H29 119.4 . . ?
 C25 C30 C1 125.0(5) . . ?
 C29 C30 C1 117.3(5) . . ?
 C29 C30 C25 117.7(5) . . ?
 C49 O5 C53 117.3(5) . . ?
 C51 O6 C54 118.8(4) . . ?
 C32 C31 H31 103.1 . . ?
 C52 C31 H31 103.1 . . ?
 C52 C31 C32 116.3(4) . . ?
 C52 C31 C60 110.0(4) . . ?
 C60 C31 H31 103.1 . . ?
 C60 C31 C32 118.6(4) . . ?
 C33 C32 C31 116.9(4) . . ?
 C33 C32 C41 100.3(4) . . ?
 C41 C32 C31 107.4(4) . . ?
 C46 C32 C31 107.7(4) . . ?
 C46 C32 C33 109.8(4) . . ?
 C46 C32 C41 114.9(4) . . ?
 O4 C33 C32 125.2(5) . . ?
 O4 C33 C34 126.4(5) . . ?
 C34 C33 C32 108.2(5) . . ?
 C33 C34 H34 124.9 . . ?
 C35 C34 C33 110.3(5) . . ?
 C35 C34 H34 124.9 . . ?
 C34 C35 C36 125.4(6) . . ?
 C34 C35 C41 110.9(5) . . ?
 C41 C35 C36 123.7(5) . . ?
 C35 C36 H36 106.1 . . ?
 C37 C36 C35 116.0(6) . . ?
 C37 C36 H36 106.1 . . ?
 C42 C36 C35 111.0(7) . . ?
 C42 C36 H36 106.1 . . ?
 C42 C36 C37 110.8(6) . . ?
 C36 C37 H37A 107.9 . . ?
 C36 C37 H37B 107.9 . . ?
 C36 C37 C38 117.7(5) . . ?
 H37A C37 H37B 107.2 . . ?
 C38 C37 H37A 107.9 . . ?
 C38 C37 H37B 107.9 . . ?
 C37 C38 H38A 110.1 . . ?
 C37 C38 H38B 110.1 . . ?
 H38A C38 H38B 108.4 . . ?
 C39 C38 C37 108.2(6) . . ?
 C39 C38 H38A 110.1 . . ?
 C39 C38 H38B 110.1 . . ?
 C38 C39 H39 113.8 . . ?
 C40 C39 C38 119.0(5) . . ?
 C40 C39 H39 113.8 . . ?
 C40 C39 C43 59.7(4) . . ?
 C43 C39 C38 125.9(7) . . ?
 C43 C39 H39 113.8 . . ?
 C39 C40 H40 113.8 . . ?
 C39 C40 C41 120.0(5) . . ?
 C41 C40 H40 113.8 . . ?
 C43 C40 C39 60.4(4) . . ?
 C43 C40 H40 113.8 . . ?
 C43 C40 C41 124.6(6) . . ?
 C32 C41 H41 110.1 . . ?
 C35 C41 C32 104.6(4) . . ?
 C35 C41 H41 110.1 . . ?
 C40 C41 C32 114.0(4) . . ?
 C40 C41 C35 107.8(4) . . ?
 C40 C41 H41 110.1 . . ?
 C36 C42 H42A 109.5 . . ?
 C36 C42 H42B 109.5 . . ?
 C36 C42 H42C 109.5 . . ?
 H42A C42 H42B 109.5 . . ?
 H42A C42 H42C 109.5 . . ?
 H42B C42 H42C 109.5 . . ?
 C39 C43 C45 114.9(7) . . ?
 C40 C43 C39 59.9(4) . . ?
 C40 C43 C45 114.1(7) . . ?
 C44 C43 C39 120.9(6) . . ?
 C44 C43 C40 119.9(6) . . ?
 C44 C43 C45 115.6(7) . . ?
 C43 C44 H44A 109.5 . . ?
 C43 C44 H44B 109.5 . . ?
 C43 C44 H44C 109.5 . . ?
 H44A C44 H44B 109.5 . . ?
 H44A C44 H44C 109.5 . . ?
 H44B C44 H44C 109.5 . . ?
 C43 C45 H45A 109.5 . . ?
 C43 C45 H45B 109.5 . . ?
 C43 C45 H45C 109.5 . . ?
 H45A C45 H45B 109.5 . . ?
 H45A C45 H45C 109.5 . . ?
 H45B C45 H45C 109.5 . . ?
 C32 C46 H46A 109.5 . . ?
 C32 C46 H46B 109.5 . . ?
 C32 C46 H46C 109.5 . . ?
 H46A C46 H46B 109.5 . . ?
 H46A C46 H46C 109.5 . . ?
 H46B C46 H46C 109.5 . . ?
 C48 C47 Br2 115.0(4) . . ?
 C48 C47 C52 123.6(5) . . ?
 C52 C47 Br2 121.4(4) . . ?
 C47 C48 H48 120.8 . . ?
 C49 C48 C47 118.3(5) . . ?
 C49 C48 H48 120.8 . . ?
 O5 C49 C48 115.1(5) . . ?
 O5 C49 C50 123.9(5) . . ?
 C50 C49 C48 121.0(5) . . ?
 C49 C50 H50 120.6 . . ?
 C49 C50 C51 118.7(5) . . ?
 C51 C50 H50 120.6 . . ?
 O6 C51 C50 122.8(5) . . ?
 O6 C51 C52 113.9(4) . . ?
 C50 C51 C52 123.2(5) . . ?
 C47 C52 C31 123.2(5) . . ?
 C51 C52 C31 121.6(4) . . ?
 C51 C52 C47 115.0(5) . . ?
 O5 C53 H53A 109.5 . . ?
 O5 C53 H53B 109.5 . . ?
 O5 C53 H53C 109.5 . . ?
 H53A C53 H53B 109.5 . . ?
 H53A C53 H53C 109.5 . . ?
 H53B C53 H53C 109.5 . . ?
 O6 C54 H54A 109.5 . . ?
 O6 C54 H54B 109.5 . . ?
 O6 C54 H54C 109.5 . . ?
 H54A C54 H54B 109.5 . . ?
 H54A C54 H54C 109.5 . . ?
 H54B C54 H54C 109.5 . . ?
 C56 C55 H55 119.8 . . ?
 C56 C55 C60 120.4(5) . . ?
 C60 C55 H55 119.8 . . ?
 C55 C56 H56 119.5 . . ?
 C57 C56 C55 120.9(6) . . ?
 C57 C56 H56 119.5 . . ?
 C56 C57 H57 120.3 . . ?
 C56 C57 C58 119.4(5) . . ?
 C58 C57 H57 120.3 . . ?
 C57 C58 H58 120.4 . . ?
 C59 C58 C57 119.3(6) . . ?
 C59 C58 H58 120.4 . . ?
 C58 C59 H59 118.7 . . ?
 C58 C59 C60 122.6(5) . . ?
 C60 C59 H59 118.7 . . ?
 C55 C60 C31 125.1(5) . . ?
 C59 C60 C31 117.4(5) . . ?
 C59 C60 C55 117.5(5) . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 Br1 C17 C18 C19 179.8(4) . . . . ?
 Br1 C17 C22 C1 2.5(8) . . . . ?
 Br1 C17 C22 C21 178.6(4) . . . . ?
 O1 C3 C4 C5 -163.3(6) . . . . ?
 O2 C19 C20 C21 -177.9(5) . . . . ?
 O3 C21 C22 C1 1.5(7) . . . . ?
 O3 C21 C22 C17 -174.7(5) . . . . ?
 C1 C2 C3 O1 -91.3(7) . . . . ?
 C1 C2 C3 C4 95.3(5) . . . . ?
 C1 C2 C11 C5 -101.2(5) . . . . ?
 C1 C2 C11 C10 141.9(5) . . . . ?
 C2 C1 C22 C17 -114.0(6) . . . . ?
 C2 C1 C22 C21 70.1(6) . . . . ?
 C2 C1 C30 C25 -39.1(8) . . . . ?
 C2 C1 C30 C29 141.3(5) . . . . ?
 C2 C3 C4 C5 10.0(7) . . . . ?
 C3 C2 C11 C5 20.6(5) . . . . ?
 C3 C2 C11 C10 -96.3(5) . . . . ?
 C3 C4 C5 C6 177.3(6) . . . . ?
 C3 C4 C5 C11 4.5(7) . . . . ?
 C4 C5 C6 C7 179.6(8) . . . . ?
 C4 C5 C6 C12 43.5(11) . . . . ?
 C4 C5 C11 C2 -16.7(6) . . . . ?
 C4 C5 C11 C10 105.2(6) . . . . ?
 C5 C6 C7 C8 64.3(13) . . . . ?
 C6 C5 C11 C2 170.0(6) . . . . ?
 C6 C5 C11 C10 -68.1(7) . . . . ?
 C6 C7 C8 C9 -24.1(15) . . . . ?
 C7 C8 C9 C10 -31.3(11) . . . . ?
 C7 C8 C9 C13 -105.3(9) . . . . ?
 C8 C9 C10 C11 -0.5(9) . . . . ?
 C8 C9 C10 C13 -114.6(7) . . . . ?
 C8 C9 C13 C10 110.8(7) . . . . ?
 C8 C9 C13 C14 0.5(9) . . . . ?
 C8 C9 C13 C15 -143.9(6) . . . . ?
 C9 C10 C11 C2 -175.9(5) . . . . ?
 C9 C10 C11 C5 69.2(7) . . . . ?
 C9 C10 C13 C14 107.6(6) . . . . ?
 C9 C10 C13 C15 -109.3(6) . . . . ?
 C10 C9 C13 C14 -110.3(6) . . . . ?
 C10 C9 C13 C15 105.3(6) . . . . ?
 C11 C2 C3 O1 154.4(5) . . . . ?
 C11 C2 C3 C4 -19.0(5) . . . . ?
 C11 C5 C6 C7 -8.2(11) . . . . ?
 C11 C5 C6 C12 -144.3(7) . . . . ?
 C11 C10 C13 C9 -108.3(6) . . . . ?
 C11 C10 C13 C14 -0.7(9) . . . . ?
 C11 C10 C13 C15 142.4(6) . . . . ?
 C12 C6 C7 C8 -163.2(9) . . . . ?
 C13 C9 C10 C11 114.1(6) . . . . ?
 C13 C10 C11 C2 -103.4(6) . . . . ?
 C13 C10 C11 C5 141.6(5) . . . . ?
 C16 C2 C3 O1 32.6(8) . . . . ?
 C16 C2 C3 C4 -140.8(5) . . . . ?
 C16 C2 C11 C5 139.1(5) . . . . ?
 C16 C2 C11 C10 22.2(7) . . . . ?
 C17 C18 C19 O2 178.9(5) . . . . ?
 C17 C18 C19 C20 0.9(9) . . . . ?
 C18 C17 C22 C1 -177.6(5) . . . . ?
 C18 C17 C22 C21 -1.5(8) . . . . ?
 C18 C19 C20 C21 -0.1(8) . . . . ?
 C19 C20 C21 O3 175.2(5) . . . . ?
 C19 C20 C21 C22 -1.6(8) . . . . ?
 C20 C21 C22 C1 178.6(5) . . . . ?
 C20 C21 C22 C17 2.3(8) . . . . ?
 C22 C1 C2 C3 -60.1(6) . . . . ?
 C22 C1 C2 C11 51.4(6) . . . . ?
 C22 C1 C2 C16 175.2(4) . . . . ?
 C22 C1 C30 C25 98.2(6) . . . . ?
 C22 C1 C30 C29 -81.4(6) . . . . ?
 C22 C17 C18 C19 0.0(9) . . . . ?
 C23 O2 C19 C18 178.0(5) . . . . ?
 C23 O2 C19 C20 -4.1(9) . . . . ?
 C24 O3 C21 C20 7.0(7) . . . . ?
 C24 O3 C21 C22 -176.0(5) . . . . ?
 C25 C26 C27 C28 0.2(10) . . . . ?
 C26 C25 C30 C1 179.5(6) . . . . ?
 C26 C25 C30 C29 -0.9(9) . . . . ?
 C26 C27 C28 C29 -0.6(9) . . . . ?
 C27 C28 C29 C30 0.2(9) . . . . ?
 C28 C29 C30 C1 -179.8(5) . . . . ?
 C28 C29 C30 C25 0.5(8) . . . . ?
 C30 C1 C2 C3 74.9(6) . . . . ?
 C30 C1 C2 C11 -173.6(4) . . . . ?
 C30 C1 C2 C16 -49.8(6) . . . . ?
 C30 C1 C22 C17 107.8(6) . . . . ?
 C30 C1 C22 C21 -68.0(6) . . . . ?
 C30 C25 C26 C27 0.5(10) . . . . ?
 Br2 C47 C48 C49 178.9(4) . . . . ?
 Br2 C47 C52 C31 4.3(7) . . . . ?
 Br2 C47 C52 C51 179.2(4) . . . . ?
 O4 C33 C34 C35 -164.8(6) . . . . ?
 O5 C49 C50 C51 -178.3(5) . . . . ?
 O6 C51 C52 C31 -0.4(7) . . . . ?
 O6 C51 C52 C47 -175.4(4) . . . . ?
 C31 C32 C33 O4 -89.4(7) . . . . ?
 C31 C32 C33 C34 94.6(5) . . . . ?
 C31 C32 C41 C35 -99.8(5) . . . . ?
 C31 C32 C41 C40 142.8(5) . . . . ?
 C32 C31 C52 C47 -113.7(5) . . . . ?
 C32 C31 C52 C51 71.7(6) . . . . ?
 C32 C31 C60 C55 -36.4(7) . . . . ?
 C32 C31 C60 C59 145.1(5) . . . . ?
 C32 C33 C34 C35 11.1(7) . . . . ?
 C33 C32 C41 C35 22.8(5) . . . . ?
 C33 C32 C41 C40 -94.6(5) . . . . ?
 C33 C34 C35 C36 -176.3(6) . . . . ?
 C33 C34 C35 C41 4.8(7) . . . . ?
 C34 C35 C36 C37 -131.0(7) . . . . ?
 C34 C35 C36 C42 101.3(8) . . . . ?
 C34 C35 C41 C32 -18.5(6) . . . . ?
 C34 C35 C41 C40 103.2(6) . . . . ?
 C35 C36 C37 C38 -49.4(9) . . . . ?
 C36 C35 C41 C32 162.6(6) . . . . ?
 C36 C35 C41 C40 -75.7(7) . . . . ?
 C36 C37 C38 C39 82.4(7) . . . . ?
 C37 C38 C39 C40 -71.5(8) . . . . ?
 C37 C38 C39 C43 -143.5(6) . . . . ?
 C38 C39 C40 C41 -1.7(9) . . . . ?
 C38 C39 C40 C43 -116.9(8) . . . . ?
 C38 C39 C43 C40 105.8(7) . . . . ?
 C38 C39 C43 C44 -3.2(10) . . . . ?
 C38 C39 C43 C45 -149.7(7) . . . . ?
 C39 C40 C41 C32 -176.2(5) . . . . ?
 C39 C40 C41 C35 68.2(7) . . . . ?
 C39 C40 C43 C44 110.6(7) . . . . ?
 C39 C40 C43 C45 -105.8(7) . . . . ?
 C40 C39 C43 C44 -108.9(7) . . . . ?
 C40 C39 C43 C45 104.6(7) . . . . ?
 C41 C32 C33 O4 155.0(5) . . . . ?
 C41 C32 C33 C34 -21.0(5) . . . . ?
 C41 C35 C36 C37 47.7(10) . . . . ?
 C41 C35 C36 C42 -80.0(8) . . . . ?
 C41 C40 C43 C39 -107.9(6) . . . . ?
 C41 C40 C43 C44 2.7(9) . . . . ?
 C41 C40 C43 C45 146.3(6) . . . . ?
 C42 C36 C37 C38 78.3(8) . . . . ?
 C43 C39 C40 C41 115.3(7) . . . . ?
 C43 C40 C41 C32 -103.4(6) . . . . ?
 C43 C40 C41 C35 141.1(6) . . . . ?
 C46 C32 C33 O4 33.7(7) . . . . ?
 C46 C32 C33 C34 -142.3(5) . . . . ?
 C46 C32 C41 C35 140.5(5) . . . . ?
 C46 C32 C41 C40 23.0(7) . . . . ?
 C47 C48 C49 O5 -179.8(5) . . . . ?
 C47 C48 C49 C50 1.4(8) . . . . ?
 C48 C47 C52 C31 -175.5(5) . . . . ?
 C48 C47 C52 C51 -0.6(8) . . . . ?
 C48 C49 C50 C51 0.4(8) . . . . ?
 C49 C50 C51 O6 175.3(5) . . . . ?
 C49 C50 C51 C52 -2.5(8) . . . . ?
 C50 C51 C52 C31 177.5(5) . . . . ?
 C50 C51 C52 C47 2.6(7) . . . . ?
 C52 C31 C32 C33 -62.0(6) . . . . ?
 C52 C31 C32 C41 49.7(6) . . . . ?
 C52 C31 C32 C46 173.9(4) . . . . ?
 C52 C31 C60 C55 101.0(6) . . . . ?
 C52 C31 C60 C59 -77.5(6) . . . . ?
 C52 C47 C48 C49 -1.3(8) . . . . ?
 C53 O5 C49 C48 175.4(5) . . . . ?
 C53 O5 C49 C50 -5.9(8) . . . . ?
 C54 O6 C51 C50 5.5(7) . . . . ?
 C54 O6 C51 C52 -176.5(5) . . . . ?
 C55 C56 C57 C58 0.9(9) . . . . ?
 C56 C55 C60 C31 -179.5(5) . . . . ?
 C56 C55 C60 C59 -1.0(8) . . . . ?
 C56 C57 C58 C59 -1.3(9) . . . . ?
 C57 C58 C59 C60 0.5(9) . . . . ?
 C58 C59 C60 C31 179.3(5) . . . . ?
 C58 C59 C60 C55 0.6(8) . . . . ?
 C60 C31 C32 C33 72.8(6) . . . . ?
 C60 C31 C32 C41 -175.5(4) . . . . ?
 C60 C31 C32 C46 -51.3(6) . . . . ?
 C60 C31 C52 C47 107.8(5) . . . . ?
 C60 C31 C52 C51 -66.7(6) . . . . ?
 C60 C55 C56 C57 0.3(9) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
