Hydro­gen bonding in thia­crown complexes: chloro­bis­(nicotin­amide-κN)(1,4,7-tri­thia­cyclo­nonane-κ3S)­ruthenium(II) hexa­fluoro­phosphate monohydrate

Adams, H.; Shan, N.; Thomas, J.

doi:10.1107/S1600536804009602

metal-organic compounds

CRYSTALLOGRAPHIC

COMMUNICATIONS

ISSN: 2056-9890

Volume 60| Part 5| May 2004| Pages m662-m663

https://doi.org/10.1107/S1600536804009602

Hydrogen bonding in thiacrown complexes: chlorobis(nicotinamide-κN)(1,4,7-trithiacyclononane-κ³S)ruthenium(II) hexafluorophosphate monohydrate

Harry Adams,^a ^* N. Shan ^a and J. Thomas ^a

^aDepartment of Chemistry, Dainton Building, University of Sheffield, Sheffield S7 3HF, England

^*Correspondence e-mail: [email protected]

(Received 10 March 2004; accepted 20 April 2004; online 30 April 2004)

The title complex, [RuClL₂([9]-ane-S₃)]PF₆·H₂O [where L is nicotinamide, C₇H₆N₂O) and [9]-ane-S₃ is 1,4,7-trithiacyclononane (C₆H₁₂S₃)], was isolated as a hexafluorophosphate salt from water–ethanol. The structure confirms that the amide moieties are available for possible mutual hydrogen-bond interactions. However, from aqueous solvents, these sites are involved in networks of interactions with water molecules.

Comment

The targeted design of long-range solid-state structures, or crystal engineering, is a fast-emerging area of chemistry. In this context, structures mediated by ligand coordination to specific metal centres has been particularly well pursued. However, comparatively less work has involved coordination complexes with coordinated ligands containing hydrogen-bonding sites. As part of a programme investigating the possible assembly of solution- and solid-phase host structures, we are synthesizing complexes based on Ru^II centres facially capped by thiacrown ligands. Coordination of two or three nicotinic and isonicotinic acid derivatives to these centres provides two- and three-dimensional synthons for crystal engineering. Solubility properties of the resultant complexes can be modulated by a change of counter-ion. The complexes are initially synthesized as chloride salts, but anion metathesis affords a route to a variety of other counter-ions. Using this methodology, we are exploring the effect of the counter-ion on the long-range structure of the resulting crystallographic architecture. We report here the structure of [RuClL₂([9]-ane-S₃)]PF₆ (where L is nicotinamide and [9]-ane-S₃ is 1,4,7-trithiacyclononane) grown from water–ethanol as a monohydrate, (I), in which the water molecules interact with the projecting amide groups.

Figure 1

View of (I

), showing the numbering scheme, with displacement ellipsoids drawn at the 50% probability level.

Experimental

[RuCl₂(DMSO)([9]-ane-S₃)] (0.215 g, 0.5 mmol) and nicotinamide (0.122 g, 1.0 mmol) were heated at reflux for 4 h under a nitrogen atmosphere in 30 ml of a water–ethanol mixture (1:1). The reaction mixture was allowed to cool and any insoluble material was removed by filtration. Addition of ammonium hexafluorophosphate (0.163 g, 1.0 mmol) led to the crystallization of the final product. This was collected by filtration, washed with (3 × 10 ml) portions of water, ethanol and diethyl ether, and allowed to dry in vacuo. The product was obtained as a yellow powder (yield 0.178 g, 50%). Crystals suitable for X-ray crystallography were obtained via slow evaporation from the water:ethanol mother liquor.

Crystal data

[RuCl(C₆H₆N₂O)₂(C₆H₁₂S₃)](PF₆)·H₂O
M_r = 724.10
Monoclinic, P2₁/c
a = 12.9575 (15) Å
b = 9.8190 (11) Å
c = 20.974 (3) Å
β = 101.483 (2)°
V = 2615.1 (5) Å³
Z = 4
D_x = 1.839 Mg m⁻³
Mo Kα radiation
Cell parameters from 4801 reflections
θ = 5.2–54.6°
μ = 1.08 mm⁻¹
T = 150 (2) K
Block, yellow
0.32 × 0.28 × 0.21 mm

Data collection

Bruker SMART 1000 diffractometer
ω scans
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.725, T_max = 0.806
28 430 measured reflections
5948 independent reflections
4693 reflections with I > 2σ(I)
R_int = 0.039
θ_max = 27.6°
h = −16 → 16
k = −12 → 12
l = −27 → 26

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.116
S = 1.05
5948 reflections
334 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.0573P)² + 5.2806P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 1.49 e Å⁻³
Δρ_min = −0.72 e Å⁻³

The H atoms were introduced at calculated positions and treated as riding atoms, with bond lengths of NH₂ 0.88 Å, 0.95(C—H aromatic), and 0.99 Å (CH₂). The exception being the water O—H lengths which were found by low-theta difference Fourier, then restrained to 0.85 (1) Å. The thermal displacement parameters were all made equal to 1.2 times U_eq (parent N, O or C atom).

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536804009602/su6086sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536804009602/su6086Isup2.hkl

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

chlorobis(nicotinamide-κN)(1,4,7-trithiacyclononane-κ³S)ruthenium(II) hexafluorophosphate monohydrate top

Crystal data top

[RuCl(C₆H₆N₂O)₂(C₆H₁₂S₃)](PF₆)·H₂O	F(000) = 1456
M_r = 724.10	D_x = 1.839 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.9575 (15) Å	Cell parameters from 4801 reflections
b = 9.8190 (11) Å	θ = 5.2–54.6°
c = 20.974 (3) Å	µ = 1.08 mm⁻¹
β = 101.483 (2)°	T = 150 K
V = 2615.1 (5) Å³	Block, yellow
Z = 4	0.32 × 0.28 × 0.21 mm

Data collection top

Bruker SMART 1000 diffractometer	5948 independent reflections
Radiation source: fine-focus sealed tube	4693 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 27.6°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −16→16
T_min = 0.725, T_max = 0.806	k = −12→12
28430 measured reflections	l = −27→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0573P)² + 5.2806P] where P = (F_o² + 2F_c²)/3
5948 reflections	(Δ/σ)_max = 0.001
334 parameters	Δρ_max = 1.49 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ru1	0.19776 (2)	0.70164 (3)	0.319483 (13)	0.01861 (10)
Cl1	0.01847 (8)	0.66421 (10)	0.25691 (5)	0.0308 (2)
S1	0.36636 (7)	0.70302 (9)	0.37723 (4)	0.0231 (2)
S2	0.16145 (8)	0.53152 (10)	0.38655 (5)	0.0273 (2)
S3	0.24794 (7)	0.54053 (9)	0.25309 (4)	0.0243 (2)
N1	0.1462 (2)	0.8586 (3)	0.37745 (15)	0.0223 (6)
N2	0.2257 (2)	0.8604 (3)	0.25466 (14)	0.0214 (6)
N3	0.0935 (3)	1.0985 (3)	0.05677 (15)	0.0253 (7)
H3A	0.0523	1.1057	0.0181	0.030*
H3B	0.1261	1.1708	0.0757	0.030*
N4	−0.1557 (3)	1.1008 (3)	0.41734 (16)	0.0282 (7)
H4A	−0.2235	1.1055	0.4174	0.034*
H4B	−0.1166	1.1746	0.4241	0.034*
O1	0.0627 (2)	0.8725 (3)	0.06244 (13)	0.0280 (6)
O2	−0.1639 (2)	0.8741 (3)	0.39730 (14)	0.0285 (6)
C1	0.3748 (3)	0.5650 (4)	0.43730 (19)	0.0297 (9)
H1A	0.3978	0.4801	0.4188	0.036*
H1B	0.4281	0.5887	0.4765	0.036*
C2	0.2704 (3)	0.5417 (4)	0.45614 (19)	0.0335 (9)
H2A	0.2568	0.6170	0.4848	0.040*
H2B	0.2737	0.4560	0.4813	0.040*
C3	0.1930 (3)	0.3712 (4)	0.3486 (2)	0.0336 (9)
H3D	0.2651	0.3421	0.3691	0.040*
H3E	0.1435	0.2993	0.3565	0.040*
C4	0.1861 (3)	0.3866 (4)	0.2762 (2)	0.0331 (9)
H4D	0.1109	0.3867	0.2544	0.040*
H4E	0.2197	0.3066	0.2601	0.040*
C5	0.3877 (3)	0.5047 (4)	0.2854 (2)	0.0325 (9)
H5A	0.3940	0.4260	0.3155	0.039*
H5B	0.4230	0.4807	0.2492	0.039*
C6	0.4411 (3)	0.6278 (4)	0.3213 (2)	0.0315 (9)
H6A	0.4519	0.6974	0.2891	0.038*
H6B	0.5113	0.6004	0.3460	0.038*
C7	0.2126 (3)	0.9549 (4)	0.40857 (18)	0.0268 (8)
H7	0.2858	0.9455	0.4095	0.032*
C8	0.1787 (3)	1.0653 (4)	0.43880 (19)	0.0280 (8)
H8	0.2277	1.1311	0.4597	0.034*
C9	0.0724 (3)	1.0800 (4)	0.43849 (18)	0.0264 (8)
H9	0.0470	1.1568	0.4582	0.032*
C10	0.0037 (3)	0.9801 (4)	0.40874 (18)	0.0229 (7)
C11	0.0435 (3)	0.8715 (4)	0.37911 (17)	0.0232 (8)
H11	−0.0039	0.8031	0.3591	0.028*
C12	0.3037 (3)	0.9516 (4)	0.27140 (19)	0.0259 (8)
H12	0.3473	0.9451	0.3134	0.031*
C13	0.3237 (3)	1.0540 (4)	0.23064 (19)	0.0291 (9)
H13	0.3800	1.1159	0.2446	0.035*
C14	0.2612 (3)	1.0660 (4)	0.16944 (19)	0.0269 (8)
H14	0.2731	1.1361	0.1405	0.032*
C15	0.1807 (3)	0.9730 (4)	0.15150 (17)	0.0217 (7)
C16	0.1654 (3)	0.8718 (4)	0.19481 (17)	0.0224 (7)
H16	0.1102	0.8080	0.1817	0.027*
C17	0.1064 (3)	0.9782 (4)	0.08650 (18)	0.0231 (8)
C18	−0.1124 (3)	0.9821 (4)	0.40712 (17)	0.0249 (8)
P1	0.46884 (10)	0.82344 (13)	0.59334 (6)	0.0403 (3)
F1	0.3684 (3)	0.8500 (4)	0.53914 (19)	0.0786 (11)
F2	0.5298 (3)	0.7825 (4)	0.5370 (2)	0.0902 (13)
F3	0.5049 (3)	0.9775 (4)	0.5886 (2)	0.0944 (14)
F4	0.5742 (3)	0.7989 (3)	0.6439 (2)	0.0896 (14)
F5	0.4085 (4)	0.8643 (6)	0.6465 (2)	0.1205 (18)
F6	0.4388 (3)	0.6669 (3)	0.59625 (16)	0.0671 (9)
O1W	0.6483 (3)	0.7735 (4)	0.4320 (3)	0.0801 (14)
H2W	0.6918	0.8241	0.4177	0.096*
H1W	0.6300	0.7398	0.4654	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.01819 (16)	0.01820 (15)	0.01811 (16)	−0.00032 (11)	0.00040 (11)	0.00068 (11)
Cl1	0.0258 (5)	0.0314 (5)	0.0331 (5)	0.0003 (4)	0.0007 (4)	−0.0005 (4)
S1	0.0199 (4)	0.0265 (5)	0.0211 (5)	−0.0004 (3)	−0.0003 (3)	0.0007 (3)
S2	0.0281 (5)	0.0257 (5)	0.0288 (5)	−0.0024 (4)	0.0072 (4)	0.0045 (4)
S3	0.0267 (5)	0.0230 (5)	0.0222 (5)	0.0003 (4)	0.0022 (4)	−0.0019 (3)
N1	0.0216 (15)	0.0190 (15)	0.0237 (16)	0.0014 (12)	−0.0015 (12)	−0.0002 (12)
N2	0.0219 (15)	0.0203 (15)	0.0210 (16)	0.0002 (12)	0.0016 (12)	−0.0002 (12)
N3	0.0309 (17)	0.0191 (15)	0.0223 (16)	−0.0008 (13)	−0.0034 (13)	0.0025 (12)
N4	0.0291 (17)	0.0198 (16)	0.0355 (19)	0.0016 (13)	0.0063 (14)	−0.0016 (13)
O1	0.0343 (15)	0.0175 (13)	0.0267 (14)	−0.0008 (11)	−0.0072 (11)	0.0012 (11)
O2	0.0281 (14)	0.0205 (13)	0.0364 (16)	0.0002 (11)	0.0055 (12)	0.0008 (11)
C1	0.033 (2)	0.029 (2)	0.0222 (19)	0.0042 (16)	−0.0065 (16)	0.0018 (15)
C2	0.040 (2)	0.038 (2)	0.022 (2)	−0.0009 (19)	0.0062 (17)	0.0072 (17)
C3	0.039 (2)	0.0176 (19)	0.043 (2)	−0.0002 (16)	0.0047 (19)	0.0028 (17)
C4	0.036 (2)	0.0218 (19)	0.040 (2)	−0.0028 (16)	0.0035 (18)	−0.0024 (17)
C5	0.027 (2)	0.036 (2)	0.034 (2)	0.0044 (17)	0.0051 (17)	−0.0008 (18)
C6	0.0220 (19)	0.042 (2)	0.031 (2)	0.0015 (17)	0.0068 (16)	−0.0005 (18)
C7	0.025 (2)	0.028 (2)	0.026 (2)	−0.0007 (15)	0.0020 (16)	0.0030 (15)
C8	0.032 (2)	0.0240 (19)	0.026 (2)	−0.0046 (16)	−0.0007 (16)	−0.0032 (15)
C9	0.033 (2)	0.0224 (19)	0.0227 (19)	0.0022 (15)	0.0032 (16)	−0.0019 (14)
C10	0.0262 (19)	0.0222 (18)	0.0201 (18)	0.0029 (14)	0.0037 (15)	0.0040 (14)
C11	0.0283 (19)	0.0210 (18)	0.0196 (18)	−0.0031 (15)	0.0030 (15)	0.0007 (14)
C12	0.0226 (19)	0.031 (2)	0.0224 (19)	−0.0030 (15)	−0.0007 (15)	0.0022 (15)
C13	0.029 (2)	0.029 (2)	0.029 (2)	−0.0108 (16)	0.0015 (16)	0.0008 (16)
C14	0.028 (2)	0.0259 (19)	0.026 (2)	−0.0031 (15)	0.0043 (16)	0.0072 (15)
C15	0.0243 (18)	0.0195 (17)	0.0208 (18)	0.0025 (14)	0.0034 (14)	−0.0006 (14)
C16	0.0217 (18)	0.0216 (18)	0.0227 (19)	0.0001 (14)	0.0014 (14)	−0.0021 (14)
C17	0.0222 (18)	0.0247 (19)	0.0219 (19)	0.0021 (14)	0.0031 (15)	0.0018 (14)
C18	0.030 (2)	0.0229 (19)	0.0198 (18)	0.0015 (15)	0.0017 (15)	0.0022 (14)
P1	0.0343 (6)	0.0412 (7)	0.0387 (7)	0.0108 (5)	−0.0085 (5)	−0.0105 (5)
F1	0.062 (2)	0.079 (2)	0.079 (2)	0.0124 (19)	−0.0238 (18)	0.002 (2)
F2	0.076 (3)	0.113 (3)	0.091 (3)	−0.015 (2)	0.039 (2)	−0.030 (2)
F3	0.080 (3)	0.046 (2)	0.138 (4)	0.0003 (18)	−0.027 (2)	−0.002 (2)
F4	0.079 (3)	0.059 (2)	0.102 (3)	0.0182 (18)	−0.052 (2)	−0.020 (2)
F5	0.115 (4)	0.178 (5)	0.079 (3)	0.011 (3)	0.045 (3)	−0.060 (3)
F6	0.078 (2)	0.0551 (19)	0.059 (2)	−0.0091 (17)	−0.0070 (17)	0.0022 (15)
O1W	0.062 (3)	0.062 (3)	0.125 (4)	−0.018 (2)	0.040 (3)	−0.035 (3)

Geometric parameters (Å, º) top

Ru1—N2	2.146 (3)	C4—H4E	0.9900
Ru1—N1	2.150 (3)	C5—C6	1.516 (6)
Ru1—S1	2.2773 (9)	C5—H5A	0.9900
Ru1—S3	2.2859 (10)	C5—H5B	0.9900
Ru1—S2	2.2922 (10)	C6—H6A	0.9900
Ru1—Cl1	2.4579 (10)	C6—H6B	0.9900
S1—C6	1.820 (4)	C7—C8	1.372 (5)
S1—C1	1.839 (4)	C7—H7	0.9500
S2—C2	1.820 (4)	C8—C9	1.384 (6)
S2—C3	1.847 (4)	C8—H8	0.9500
S3—C4	1.821 (4)	C9—C10	1.386 (5)
S3—C5	1.837 (4)	C9—H9	0.9500
N1—C11	1.344 (5)	C10—C11	1.384 (5)
N1—C7	1.355 (5)	C10—C18	1.498 (5)
N2—C12	1.344 (5)	C11—H11	0.9500
N2—C16	1.344 (5)	C12—C13	1.377 (5)
N3—C17	1.330 (5)	C12—H12	0.9500
N3—H3A	0.8800	C13—C14	1.380 (5)
N3—H3B	0.8800	C13—H13	0.9500
N4—C18	1.329 (5)	C14—C15	1.381 (5)
N4—H4A	0.8800	C14—H14	0.9500
N4—H4B	0.8800	C15—C16	1.387 (5)
O1—C17	1.240 (4)	C15—C17	1.505 (5)
O2—C18	1.248 (4)	C16—H16	0.9500
C1—C2	1.501 (6)	P1—F5	1.537 (4)
C1—H1A	0.9900	P1—F1	1.570 (3)
C1—H1B	0.9900	P1—F4	1.571 (3)
C2—H2A	0.9900	P1—F6	1.590 (3)
C2—H2B	0.9900	P1—F3	1.592 (4)
C3—C4	1.510 (6)	P1—F2	1.598 (4)
C3—H3D	0.9900	O1W—H2W	0.8501
C3—H3E	0.9900	O1W—H1W	0.8499
C4—H4D	0.9900

N2—Ru1—N1	87.02 (12)	S3—C5—H5A	109.6
N2—Ru1—S1	93.89 (8)	C6—C5—H5B	109.6
N1—Ru1—S1	93.92 (8)	S3—C5—H5B	109.6
N2—Ru1—S3	90.72 (8)	H5A—C5—H5B	108.1
N1—Ru1—S3	176.98 (8)	C5—C6—S1	113.2 (3)
S1—Ru1—S3	88.23 (4)	C5—C6—H6A	108.9
N2—Ru1—S2	177.81 (8)	S1—C6—H6A	108.9
N1—Ru1—S2	92.89 (9)	C5—C6—H6B	108.9
S1—Ru1—S2	88.30 (4)	S1—C6—H6B	108.9
S3—Ru1—S2	89.29 (4)	H6A—C6—H6B	107.7
N2—Ru1—Cl1	91.77 (8)	N1—C7—C8	122.9 (4)
N1—Ru1—Cl1	92.40 (8)	N1—C7—H7	118.6
S1—Ru1—Cl1	171.72 (4)	C8—C7—H7	118.6
S3—Ru1—Cl1	85.67 (3)	C7—C8—C9	119.4 (4)
S2—Ru1—Cl1	86.05 (4)	C7—C8—H8	120.3
C6—S1—C1	100.11 (19)	C9—C8—H8	120.3
C6—S1—Ru1	103.42 (13)	C8—C9—C10	118.5 (3)
C1—S1—Ru1	106.27 (13)	C8—C9—H9	120.8
C2—S2—C3	101.0 (2)	C10—C9—H9	120.8
C2—S2—Ru1	103.34 (14)	C11—C10—C9	119.0 (3)
C3—S2—Ru1	105.44 (14)	C11—C10—C18	117.5 (3)
C4—S3—C5	101.3 (2)	C9—C10—C18	123.5 (3)
C4—S3—Ru1	102.61 (14)	N1—C11—C10	122.9 (3)
C5—S3—Ru1	106.66 (14)	N1—C11—H11	118.5
C11—N1—C7	117.3 (3)	C10—C11—H11	118.5
C11—N1—Ru1	120.2 (2)	N2—C12—C13	123.3 (3)
C7—N1—Ru1	122.2 (3)	N2—C12—H12	118.4
C12—N2—C16	117.1 (3)	C13—C12—H12	118.4
C12—N2—Ru1	122.1 (2)	C12—C13—C14	119.5 (4)
C16—N2—Ru1	120.8 (2)	C12—C13—H13	120.3
C17—N3—H3A	120.0	C14—C13—H13	120.3
C17—N3—H3B	120.0	C13—C14—C15	118.0 (3)
H3A—N3—H3B	120.0	C13—C14—H14	121.0
C18—N4—H4A	120.0	C15—C14—H14	121.0
C18—N4—H4B	120.0	C14—C15—C16	119.6 (3)
H4A—N4—H4B	120.0	C14—C15—C17	122.4 (3)
C2—C1—S1	111.0 (3)	C16—C15—C17	118.0 (3)
C2—C1—H1A	109.4	N2—C16—C15	122.6 (3)
S1—C1—H1A	109.4	N2—C16—H16	118.7
C2—C1—H1B	109.4	C15—C16—H16	118.7
S1—C1—H1B	109.4	O1—C17—N3	123.2 (3)
H1A—C1—H1B	108.0	O1—C17—C15	119.9 (3)
C1—C2—S2	113.2 (3)	N3—C17—C15	116.9 (3)
C1—C2—H2A	108.9	O2—C18—N4	122.8 (4)
S2—C2—H2A	108.9	O2—C18—C10	119.6 (3)
C1—C2—H2B	108.9	N4—C18—C10	117.5 (3)
S2—C2—H2B	108.9	F5—P1—F1	90.8 (3)
H2A—C2—H2B	107.8	F5—P1—F4	92.9 (3)
C4—C3—S2	112.0 (3)	F1—P1—F4	176.0 (3)
C4—C3—H3D	109.2	F5—P1—F6	93.5 (3)
S2—C3—H3D	109.2	F1—P1—F6	90.8 (2)
C4—C3—H3E	109.2	F4—P1—F6	90.70 (19)
S2—C3—H3E	109.2	F5—P1—F3	89.8 (3)
H3D—C3—H3E	107.9	F1—P1—F3	90.4 (2)
C3—C4—S3	114.2 (3)	F4—P1—F3	87.8 (2)
C3—C4—H4D	108.7	F6—P1—F3	176.5 (2)
S3—C4—H4D	108.7	F5—P1—F2	178.8 (3)
C3—C4—H4E	108.7	F1—P1—F2	88.1 (2)
S3—C4—H4E	108.7	F4—P1—F2	88.3 (3)
H4D—C4—H4E	107.6	F6—P1—F2	86.9 (2)
C6—C5—S3	110.4 (3)	F3—P1—F2	89.9 (3)
C6—C5—H5A	109.6	H2W—O1W—H1W	146.2

References

Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar

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Volume 60| Part 5| May 2004| Pages m662-m663

https://doi.org/10.1107/S1600536804009602

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