Crystal structure and Hirshfeld surface analysis of (E)-N'-benzyl-idene-4-chloro-benzene-sulfono-hydrazide and of its (E)-4-chloro-N'-(ortho- and para-methyl-benzyl-idene)benzene-sulfono-hydrazide derivatives.

ABSTRACT: (E)-N'-Benzyl-idene-4-chloro-benzene-sulfono-hydrazide, C13H11ClN2O2S, (I), and its ortho- and para-methyl-substituted derivatives, C14H13ClN2O2S, namely (E)-4-chloro-N'-(2-methyl-benzyl-idene)benzene-sulfono-hydrazide, (II), and (E)-4-chloro-N'-(4-methyl-benzyl-idene)benzene-sulfono-hydrazide, (III), have been synthesized, characterized spectroscopically and their crystal structures determined to investigate the effect of the substitution site of the benzyl-idene group on the structural and supra-molecular features in these compounds. Compounds (I) and (II) are isotypic while compound (III) is different. All three mol-ecules are bent at the S atom with C-S-N-N torsion angles of -66.0?(3), -66.0?(3) and -58.4?(2)° for (I), (II) and (III), respectively. The hydrazone portions of the mol-ecules, S-N-N=C, are slightly twisted from planarity, with a torsion angle of 166.5?(3)° in (I), 165.4?(3)° in (II) and 157.9?(2)° in (III). The two aromatic rings present in the compounds are inclined to each other by 78.4?(2), 74.8?(2) and 76.9?(1)° in (I), (II) and (III), respectively. In the crystal structure of the parent compound (I), and of the ortho-methyl derivative (II), an N-H?O hydrogen bond links the mol-ecules into chains along [001], which are inter-connected by weak inter-molecular C-H?O inter-actions, generating layers lying parallel to the bc plane. In the crystal of the para derivative (III), however, the packing is significantly different. Here mol-ecules are linked by pairs of N-H?O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif. The dimers are then linked by C-Cl?? inter-actions, forming ribbons propagating along [10]. Hirshfeld surface analyses show that the van der Waals inter-actions constitute the major contribution to the inter-molecular inter-actions in the crystal structures of all three compounds. The fingerprint plots indicate that the H?H contacts make the largest contributions to the Hirshfeld surfaces.

SUBMITTER: Salian AR 

PROVIDER: S-EPMC6218900 | biostudies-other | 2018 Nov

REPOSITORIES: biostudies-other