Crystal structure and Hirshfeld surface analysis of (E)-N′-benzyl­idene-4-chloro­benzene­sulfono­hydrazide and of its (E)-4-chloro-N′-(ortho- and para-methyl­benzyl­idene)benzene­sulfono­hydrazide derivatives

(E)-N′-Benzyl­idene-4-chloro­benzene­sulfono­hydrazide, C(13)H(11)ClN(2)O(2)S, (I), and its ortho- and para-methyl­substituted derivatives, C(14)H(13)ClN(2)O(2)S, namely (E)-4-chloro-N′-(2-methyl­benzyl­idene)benzene­sulfono­hydrazide, (II), and (E)-4-chloro-N′-(4-methyl­benzyl­idene)benzene­sulfono­hydrazide, (III), have been synthesized, characterized spectroscopically and their crystal structures determined to investigate the effect of the substitution site of the benzyl­idene group on the structural and supra­molecular features in these compounds. Compounds (I) and (II) are isotypic while compound (III) is different. All three mol­ecules are bent at the S atom with C—S—N—N torsion angles of −66.0 (3), −66.0 (3) and −58.4 (2)° for (I), (II) and (III), respectively. The hydrazone portions of the mol­ecules, S—N—N=C, are slightly twisted from planarity, with a torsion angle of 166.5 (3)° in (I), 165.4 (3)° in (II) and 157.9 (2)° in (III). The two aromatic rings present in the compounds are inclined to each other by 78.4 (2), 74.8 (2) and 76.9 (1)° in (I), (II) and (III), respectively. In the crystal structure of the parent compound (I), and of the ortho-methyl derivative (II), an N—H⋯O hydrogen bond links the mol­ecules into chains along [001], which are inter­connected by weak inter­molecular C—H⋯O inter­actions, generating layers lying parallel to the bc plane. In the crystal of the para derivative (III), however, the packing is significantly different. Here mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R (2) (2)(8) ring motif. The dimers are then linked by C—Cl⋯π inter­actions, forming ribbons propagating along [1[Image: see text]0]. Hirshfeld surface analyses show that the van der Waals inter­actions constitute the major contribution to the inter­molecular inter­actions in the crystal structures of all three compounds. The fingerprint plots indicate that the H⋯H contacts make the largest contributions to the Hirshfeld surfaces.