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

Abstract

The crystal structures and Hirshfeld surface analyses of three Schiff bases, namely (E)-N′-[4-(piperidin-1-yl)benzylidene]benzenesulfonohydrazide, C18H21N3O2S, (I), (E)-4-methyl-N′-[4-(piperidin-1-yl)benzylidene]benzenesulfonohydrazide, C19H23N3O2S, (II), and (E)-4-chloro-N′-[4-(piperidin-1-yl)benzylidene]benzenesulfonohydrazide, C18H20ClN3O2S, (III), derived from arylsulfonohydrazides 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 P21/c for (I) and (II), and C2/c for (III). Compound (III) contains two independent molecules in the asymmetric unit and sixteen molecules per unit cell, while (I) and (II) both have one and four molecules, respectively, in their asymmetric units and unit cells. In all cases, the central part of the molecule is twisted at the S atom. In the crystals, the molecules are linked via N—H...O hydrogen bonds, forming chains. Two-dimensional fingerprint plots of various interatomic contacts show that the major contributions are from H...H interactions.