Crystal structure and Hirshfeld surface analysis of (E)-N′-benzylidene-4-chlorobenzenesulfonohydrazide and of its (E)-4-chloro-N′-(ortho- and para-methylbenzylidene)benzenesulfonohydrazide derivatives

Abstract

The crystal structures of (E)-N′-(benzyl­idene)-4-chloro­benzene­sulfono­hydrazide (I) and its ortho- and para-methyl-substituted benzyl­idene derivatives, (E)-N′-(2-methyl­benzyl­idene)-4-chloro-benzene­sulfono­hydrazide (II) and (E)-N′-(4-methyl­benzyl­idene)-4-chloro­benzene­sulfono­hydrazide (III), have been studied to investigate the effect of substitution on the structural and supra­molecular features of these compounds.

Crystal structures and the Hirshfeld surface analysis of (E)-4-nitro-N′-(o-chloro, o- and p-methylbenzylidene)benzenesulfonohydrazides

“…The chains are linked via C-HÁ Á ÁO hydrogen bonds, forming layers. This situation is similar to that in the recently reported structures of (E)-N 0 -benzylidene-4-chlorobenzenesulfonolydrazine and the 2-methylbenzilidene derivative, (E)-N 0 -(2methylbenzylidene)-4-chlorobenzenesulfonolydrazine (Salian et al, 2018).…”

“…In all three compounds the configuration about the C N bond is E, with C7 N2 bond lengths of 1.269 (5), 1.275 (2) and 1.263 (3) Å in (I), (II) and (III), respectively. The respective N1-N2 bond lengths of 1.404 (4), 1.400 (2) and 1.398 (2) Å are consistent with the azine bond lengths of 1.40 Å in similar structures (Salian et al, 2018), indicating the delocalization of -electron density over the hydrazone portion of the molecules. The conformation of the N-H and C-H bonds in (I) and (II), with respect to the orthosubstituents, are syn to each other ( Figs.…”

“…Structures similar to the title compounds that have been reported in the literature include (Hussain et al, 2017b). (E)-N 0 -(2-methylbenzylidene)-4-chlorobenzenesulfonohydrazide and (E)-N 0 -(4-methylbenzylidene)-4chlorobenzenesulfonohydrazide (Salian et al, 2018). In all the structures, intermolecular N-HÁ Á ÁO hydrogen bonds link neighbouring molecules to form chains, which are linked byinteractions, further stabilizing the crystal structures.…”

“…Organic polymers containing the azomethine group are known to have good mechanical strength (Morgan et al, 1987) and high thermal stability (Catanescu et al, 2001). As part of our continuing studies to explore the effect of the nature and site of substituents on the crystal structures of sulfonyl hydrazide derivatives (Salian et al, 2018), we report herein the synthesis, crystal structures and Hirshfeld surface analyses of the title compounds, (E)-4-nitro-N 0 -(2-chlorobenzylidene)benzenesulfonohydrazide (I), (E)-4-nitro-N 0 -(2-methylbenzylidene)benzenesulfonohydrazide (II) and (E)-4-nitro-N 0 -(4-methylbenzylidene)benzenesulfonohydrazide monohydrate (III).…”

Crystal structure and Hirshfeld surface analysis of two (E)-N′-(para-substituted benzylidene) 4-chlorobenzenesulfonohydrazides

“…Arylsulfonylhydrazones have shown antitumour activity in addition to their role as a versatile source of diazo compounds in many metal-catalysed and metal-free reactions (Hashemi, 2012). In a continuation of our efforts to explore the effect of site and nature of substituents on the crystal structures of 4-chloroarylsulfonohydrazide derivatives (Salian et al, 2018), we report herein the synthesis, characterization, crystal structures ISSN 2056-9890 and Hirshfeld surface analysis of the title compounds, (I) and (II), and compare them with those of the recently reported structures of (E)-4-chloro-N 0 -(benzylidene) benzenesulfonohydrazide (III), (E)-4-chloro-N 0 -(2-methylbenzylidene)benzenesulfonohydrazide (IV) and (E)-4-chloro-N 0 -(4methylbenzylidene)benzenesulfonohydrazide (V) (Salian et al, 2018).…”