Crystal structure of (E)-N'-(4-chloro-benzyl-idene)-4-methyl-benzene-sulfono-hydrazide: a hexa-gonal polymorph

Abstract

The title compound, C14H13ClN2O2S, crystallized in the enanti-omorphic defining hexa-gonal space group P61 [Flack parameter = -0.02 (7)]. The partially hydrated form of the same compound, crystallizing in the triclinic space group P-1, has been reported previously [Kia et al. (2009b). Acta Cryst. E65, o1119], as has the crystal structure of the bromo derivative, also crystallizing in the space group P-1 [Kia et al. (2009a). Acta Cryst. E65, o821]. The title mol-ecule is non-planar with the planes of the benzene rings being inclined to one another by 76.62 (13)°, and has an E conformation about the C=N bond. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds forming 61 helical chains running along [001]. The chains are linked via C-H⋯O hydrogen bonds, C-H⋯π inter-actions and short Cl⋯O [3.015 (3) Å] inter-actions, forming a three-dimensional structure.

Keywords: Schiff base; crystal structure; helical chains; hydrazones; hydrogen bonding.; sulfono­hydrazide.

Fig. 1.

The molecular structure of the title compound, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level.

Fig. 2.

A view along the c axis of the crystal packing of the title compound. The N—H···O and C—H···O hydrogen bonds are indicated by dashed lines (see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity).