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Crystal structure and Hirshfeld surface analysis of two (E)-N'-(para-substituted benzyl-idene) 4-chloro-benzene-sulfono-hydrazides.

ABSTRACT: Two (E)-N'-(p-substituted benzyl-idene)-4-chloro-benzene-sulfono-hydrazides, namely, (E)-4-chloro-N'-(4-chloro-benzyl-idene)benzene-sulfono-hydrazide, C13H10Cl2N2O2S, (I), and (E)-4-chloro-N'-(4-nitro-benzyl-idene)benzene-sulfono-hydrazide, C13H10ClN3O4S, (II), have been synthesized, characterized and their crystal structures studied to explore the effect of the nature of substituents on the structural parameters. Compound (II) crystallized with two independent mol-ecules [(IIA) and IIB)] in the asymmetric unit. In both compounds, the configuration around the C=N bond is E. The mol-ecules are twisted at the S atom with C-S-N-N torsion angles of -62.4?(2)° in (I), and -46.8?(2)° and 56.8?(2)° in the mol-ecules A and B of (II). The 4-chloro-phenyl-sulfonyl and 4-substituted benzyl-idene rings form dihedral angles of 81.0?(1)° in (I), 75.9?(1)° in (IIA) and 73.4?(1)° in (IIB). In the crystal of (I), mol-ecules are linked via pairs of N-H?O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif. The dimers are linked by C-Cl?? inter-actions, forming a three-dimensional structure. In the crystal of (II), mol-ecules are linked by C-H?? inter-actions and N-H?O hydrogen bonds, forming -A-B-A-B- chains along the c-axis direction. The chains are linked via C-H?O and C-H?? inter-actions, forming layers parallel to the bc plane. Two-dimensional fingerprint plots show that the most significant contacts contributing to the Hirshfeld surface for (I) are H?H contacts (26.6%), followed by Cl?H/H?Cl (21.3%), O?H/H?O (15.5%) and Cl?C/C?Cl (10.7%), while for (II) the O?H/H?O contacts are dominant, with a contribution of 34.8%, followed by H?H (15.2%), C?H/H?C (14.0%) and Cl?H/H?Cl (10.0%) contacts.

SUBMITTER: Salian AR

PROVIDER: S-EPMC6281117 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Crystal structure and Hirshfeld surface analysis of two (E)-N'-(para-substituted benzyl-idene) 4-chloro-benzene-sulfono-hydrazides.

Salian Akshatha R AR Foro Sabine S Gowda B Thimme BT

Acta crystallographica. Section E, Crystallographic communications 20181116 Pt 12

Two (E)-N'-(p-substituted benzyl-idene)-4-chloro-benzene-sulfono-hydrazides, namely, (E)-4-chloro-N'-(4-chloro-benzyl-idene)benzene-sulfono-hydrazide, C13H10Cl2N2O2S, (I), and (E)-4-chloro-N'-(4-nitro-benzyl-idene)benzene-sulfono-hydrazide, C13H10ClN3O4S, (II), have been synthesized, characterized and their crystal structures studied to explore the e ...[more]

PMID: 30574379

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Project description:The crystal structures of (E)-N'-(2-chloro-benzyl-idene)-4-nitro-benzene-sulfono-hydrazide, C13H10ClN3O4S (I), (E)-N'-(2-methyl-benzyl-idene)-4-nitro-benzene-sulfono-hydrazide, C14H13N3O4S (II), and (E)-N'-(4-methyl-benzyl-idene)-4-nitro-benzene-sulfono-hydrazide monohydrate, C14H13N3O4S·H2O (III), have been synthesized, characterized and their crystal structures determined to study the effects of the nature and sites of substitutions on the structural parameters and the hydrogen-bonding inter-actions. All three compounds crystallize in the monoclinic crystal system, with space group P21 for (I) and P21/c for (II) and (III). Compound (III) crystallizes as a monohydrate. All three compounds adopt an E configuration around the C=N bond. The mol-ecules are bent at the S atom with C-S-N-N torsion angles of -59.0?(3), 58.0?(2) and -70.2?(1)° in (I), (II) and (III), respectively. The sulfono-hydrazide parts are also non-linear, as is evident from the S-N-N-C torsional angles of 159.3?(3), -164.2?(1) and 152.3?(1)° in (I), (II) and (III), respectively, while the hydrazide parts are almost planar with the N-N=C-C torsion angles being -179.1?(3)° in (I), 176.7?(2)° in (II) and 175.0?(2)° in (III). The 4-nitro-substituted phenyl-sulfonyl and 2/4-substituted benzyl-idene rings are inclined to each other by 81.1?(1)° in (I), 81.4?(1)° in (II) and 74.4?(1)° in (III). The compounds show differences in hydrogen-bonding inter-actions. In the crystal of (I), mol-ecules are linked via N-H?O hydrogen bonds, forming C(4) chains along the a-axis direction that are inter-connected by weak C-H?O hydrogen bonds, generating layers parallel to the ac plane. In the crystal of (II), the amino H atom shows bifurcated N-H?O(O) hydrogen bonding with both O atoms of the nitro group generating C(9) chains along the b-axis direction. The chains are linked by weak C-H?O hydrogen bonds, forming a three-dimensional framework. In the crystal of (III), mol-ecules are linked by Ow-H?O, N-H?Ow and C-H?O hydrogen bonds, forming layers lying parallel to the bc plane. The fingerprint plots generated for the three compounds show that for (I) and (II) the O?H/H?O contacts make the largest contributions, while for the para-substituted compound (III), H?H contacts are the major contributors to the Hirshfeld surfaces.

Project description:(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⋯π 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.

Dataset Information

Crystal structure and Hirshfeld surface analysis of two (E)-N'-(para-substituted benzyl-idene) 4-chloro-benzene-sulfono-hydrazides.

Publications

Crystal structure and Hirshfeld surface analysis of two (<i>E</i>)-<i>N</i>'-(<i>para</i>-substituted benzyl-idene) 4-chloro-benzene-sulfono-hydrazides.

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