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The crystal structures and Hirshfeld surface analyses of three Schiff bases, namely ( E )- N '-[4-(piperidin-1-yl)benzyl-idene]benzene-sulfono-hydrazide, C 18 H 21 N 3 O 2 S, (I), ( E )-4-methyl- N '-[4-(piperidin-1-yl)benzyl-idene]benzene-sulfono-hydrazide, C 19 H 23 N 3 O 2 S, (II), and ( E )-4-chloro- N '-[4-(piperidin-1-yl)benzyl-idene]benzene-sulfono-hydrazide, C 18 H 20 ClN 3 O 2 S, (III), derived from aryl-sulfono-hydrazides and 4-(piperidin-4-yl)benzaldehyde have been analysed to investigate the effect of substituents on the structural parameters. All three structures crystallize in monoclinic crystal systems, in the space groups P 2 1 / c for (I) and (II), and C 2/ c for (III). Compound (III) contains two independent mol-ecules in the asymmetric unit and sixteen mol-ecules per unit cell, while (I) and (II) both have one and four mol-ecules, respectively, in their asymmetric units and unit cells. In all cases, the central part of the mol-ecule is twisted at the S atom. In the crystals, the mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains. Two-dimensional fingerprint plots of various inter-atomic contacts show that the major contributions are from H⋯H inter-actions.

Crystal structure and Hirshfeld surface analysis of (E)-N′-[4-(piperidin-1-yl)benzylidene]arylsulfonohydrazides