Comparison of the crystal structures and Hirshfeld surface analysis of five N‐(4‐methylbenzenesulfonyl)glycine hydrazone derivatives

• Published in: Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2018-11, Vol.74 (11), p.1553-1560
• Main Authors: Purandara, H., Foro, Sabine, Thimme Gowda, B.
• Format: Article
• Language: English
• Subjects: conformation; Crystal structure; Crystals; Derivatives; Dimers; Glycine; Hirshfeld surface analysis; Hydrazones; hydrogen‐bond interaction; N‐acylhydrazone derivatives; ring motif; Sulfonamides; Surface analysis (chemical); Torsion
• ISSN: 2053-2296; 0108-2701; 2053-2296; 1600-5759
• DOI: 10.1107/S2053229618014420

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. A new series of N‐acylhydrazone derivatives has been synthesized through the reactions of N‐(4‐methylbenzenesulfonyl)glycinyl hydrazides and para‐substituted aromatic aldehydes. The compounds adopt an E configuration about the C=N bond, while the NMR data indicate the presence of two isomers in solution.