The crystal structures of (E)-N′-(benzyl­idene)-4-chloro­benzene­sulfono­hydrazide (I) and its ortho- and para-methyl-substituted benzyl­idene derivatives, (E)-N′-(2-methyl­benzyl­idene)-4-chloro-benzene­sulfono­hydrazide (II) and (E)-N′-(4-methyl­benzyl­idene)-4-chloro­benzene­sulfono­hydrazide (III), have been studied to investigate the effect of substitution on the structural and supra­molecular features of these compounds.

The crystal structures of three N′-(aryl­idene)4-nitro­benzene­sulfono­hydrazides, namely, (E)-4-nitro-N′-(2-chloro­benzyl­idene)benzene­sulfono­hydrazide (I), (E)-4-nitro-N′-(2-methyl­benzyl­idene) benzene­sulfono­hydrazide (II) and (E)-4-nitro-N′-(4-methyl­benzyl­idene)benzene­sulfono­hydrazide (III), have been studied to investigate the effect of the nature and site of substitutions on the structural parameters and the supra­molecular features in these compounds. Hirshfeld surface analysis was also carried out to examine the contributions of the various atom–atom inter­actions in the crystal packing of the three compounds.

The crystal structures of (E)-4-chloro-N′-(4-chloro­benzyl­idene)benzene­sulfono­hydrazide and (E)-4-chloro-N′-(4-nitro­benzyl­idene)benzene­sulfono­hydrazide have been studied to investigate the effect of substituents on the structural parameters. The two-dimensional fingerprint plots of these two p-substituted compounds indicate that in the 4-chloro-substituted compound, the largest contribution to the Hirshfeld surface comes from the H⋯H contacts (26.6%), in contrast to the 34.8% contribution of the O⋯H/H⋯O contacts in the 4-nitro-substituted compound.

The title bis-amide derivative was obtained by the reaction between glutaric acid chloride and 2-nitro­aniline. The two benzene rings are twisted by angles of 79.14 (7) and 19.02 (14)° in the two independent mol­ecules. In the crystal, amide–amide inter­actions link the mol­ecules into chains running along b-axis direction.