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Comparison of the crystal structures and Hirshfeld surface analysis of five N ‐(4‐methylbenzenesulfonyl)glycine hydrazone derivatives
Author(s) -
Purandara H.,
Foro Sabine,
Thimme Gowda B.
Publication year - 2018
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229618014420
Subject(s) - hydrazone , crystal structure , chemistry , hydrogen bond , molecule , dihedral angle , crystallography , amide , stereochemistry , ring (chemistry) , organic chemistry
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, C 16 H 17 N 3 O 3 S, (I), ( E )‐ N ‐{2‐[2‐(4‐bromobenzylidene)hydrazinyl]‐2‐oxoethyl}‐4‐methylbenzenesulfonamide, C 16 H 16 BrN 3 O 3 S, (II), ( E )‐ N ‐{2‐[2‐(4‐chlorobenzylidene)hydrazinyl]‐2‐oxoethyl}‐4‐methylbenzenesulfonamide, C 16 H 16 ClN 3 O 3 S, (III), ( E )‐ N ‐(2‐{2‐[4‐(dimethylamino)benzylidene]hydrazinyl}‐2‐oxoethyl)‐4‐methylbenzenesulfonamide, C 18 H 22 N 4 O 3 S, (IV), and ( E )‐ N ‐{2‐[2‐(4‐methoxybenzylidene)hydrazinyl]‐2‐oxoethyl}‐4‐methylbenzenesulfonamide, C 17 H 19 N 3 O 4 S, (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 R 2 2 (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 R 2 2 (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.