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The crystal structures of ( E )- N '-(2-chloro-benzyl-idene)-4-nitro-benzene-sulfono-hydrazide, C 13 H 10 ClN 3 O 4 S (I), ( E )- N '-(2-methyl-benzyl-idene)-4-nitro-benzene-sulfono-hydrazide, C 14 H 13 N 3 O 4 S (II), and ( E )- N '-(4-methyl-benzyl-idene)-4-nitro-benzene-sulfono-hydrazide monohydrate, C 14 H 13 N 3 O 4 S·H 2 O (III), have been synthesized, characterized and their crystal structures determined to study the effects of the nature and sites of substitutions on the structural parameters and the hydrogen-bonding inter-actions. All three compounds crystallize in the monoclinic crystal system, with space group P 2 1 for (I) and P 2 1 / c for (II) and (III). Compound (III) crystallizes as a monohydrate. All three compounds adopt an E configuration around the C=N bond. The mol-ecules are bent at the S atom with C-S-N-N torsion angles of -59.0 (3), 58.0 (2) and -70.2 (1)° in (I), (II) and (III), respectively. The sulfono-hydrazide parts are also non-linear, as is evident from the S-N-N-C torsional angles of 159.3 (3), -164.2 (1) and 152.3 (1)° in (I), (II) and (III), respectively, while the hydrazide parts are almost planar with the N-N=C-C torsion angles being -179.1 (3)° in (I), 176.7 (2)° in (II) and 175.0 (2)° in (III). The 4-nitro-substituted phenyl-sulfonyl and 2/4-substituted benzyl-idene rings are inclined to each other by 81.1 (1)° in (I), 81.4 (1)° in (II) and 74.4 (1)° in (III). The compounds show differences in hydrogen-bonding inter-actions. In the crystal of (I), mol-ecules are linked via N-H⋯O hydrogen bonds, forming C (4) chains along the a- axis direction that are inter-connected by weak C-H⋯O hydrogen bonds, generating layers parallel to the ac plane. In the crystal of (II), the amino H atom shows bifurcated N-H⋯O(O) hydrogen bonding with both O atoms of the nitro group generating C (9) chains along the b -axis direction. The chains are linked by weak C-H⋯O hydrogen bonds, forming a three-dimensional framework. In the crystal of (III), mol-ecules are linked by O w -H⋯O, N-H⋯O w and C-H⋯O hydrogen bonds, forming layers lying parallel to the bc plane. The fingerprint plots generated for the three compounds show that for (I) and (II) the O⋯H/H⋯O contacts make the largest contributions, while for the para -substituted compound (III), H⋯H contacts are the major contributors to the Hirshfeld surfaces.

acta crystallographica. section e, crystallographic communications

Crystal structures and the Hirshfeld surface analysis of (E)-4-nitro-N′-(o-chloro, o- and p-methylbenzylidene)benzenesulfonohydrazides