Double anomeric effects and a hydrogen-bonded supramolecular motif in N,N′-bis(3-nitrophenyl)methanediamine

In the title compound, C₁₃H₁₂N₄O₄, the molecule lies on a crystallographic twofold axis. Molecules are linked into complex sheets parallel to (100) via one N—H...O and two C—H...O hydrogen bonds. Within the molecule, the 3-nitroanilino fragment is essentially planar, and the C—N—C—N—C fragment assumes a nearly perpendicular/perpendicular conformation, with C—N—C—N torsion angles of 81.18 (18)°, which is controlled by a pair of adjacent anomeric interactions. The findings constitute the first demonstration of two anomeric effects existing in one N—C—N unit.