The crystal structures of N-(4-methylbenzenesulfonyl)glycine hydrazone and four derivatives with four different substituents have been investigated, namely, (E)-N-{2-[2-(benzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H17N3O3S, (I), (E)-N-{2-[2-(4-bromobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16BrN3O3S, (II), (E)-N-{2-[2-(4-chlorobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16ClN3O3S, (III), (E)-N-(2-{2-[4-(dimethylamino)benzylidene]hydrazinyl}-2-oxoethyl)-4-methylbenzenesulfonamide, C18H22N4O3S, (IV), and (E)-N-{2-[2-(4-methoxybenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C17H19N3O4S, (V). The molecules in all five crystal structures show similar conformations and hydrogen-bonding patterns. The central part of the molecule, i.e. C-C-N-N=C, is almost linear in all the structures, with the C-C-N-N torsion angles ranging from -178.3 (1) to -180.0 (2)° and the C-N-N=C torsion angles ranging from -178.5 (4) to -179.8 (3)°. The conformation of the N-H and C=O bonds in the amide group of the hydrazone part is syn in all the compounds. In all the structures, sulfonamide and hydrazone dimers with R22(8) ring motifs are observed, which are further augmented by C-H...O interactions. A common feature of each of (I)-(V) is the formation of sulfonamide and hydrazone dimers with an R22(8) ring motif. Hirshfeld surface analyses gave fingerprint plots for H...H, O...H/H...O, N...H/H...N, C...H/H...C and other contacts. The H...H contacts show large surfaces, whereas the O...H plots show the presence of O...H/O...H contacts with the two characteristic long sharp spikes.
Keywords: Hirshfeld surface analysis; N-acylhydrazone derivatives; conformation; crystal structure; hydrogen-bond interaction; ring motif.