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

Salian, Akshatha R. ; Foro, Sabine ; Thimme Gowda, B. (2018):
Crystal structures and the Hirshfeld surface analysis of (E)-4-nitro-N′-(o-chloro, o- and p-methylbenzylidene)benzenesulfonohydrazides.
In: Acta Crystallographica Section E: Crystallographic Communications, 74 (12), pp. 1710-1716. International Union of Crystallography (IUCr), ISSN 2056-9890,
DOI: 10.1107/S2056989018015207,
[Article]

Abstract

The crystal structures of (E)-N'-(2-chlorobenzylidene)-4-nitrobenzenesulfonohydrazide, C13H10ClN3O4S (I), (E)-N'-(2-methylbenzylidene)-4-nitrobenzenesulfonohydrazide, C14H13N3O4 S (II), and (E)-N'-(4-methylbenzylidene)-4-nitrobenzenesulfonohydrazide monohydrate, C14H13N3O4S center dot 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 interactions. All three compounds crystallize in the monoclinic crystal system, with space group P2(1) for (I) and P2(1)/c for (II) and (III). Compound (III) crystallizes as a monohydrate. All three compounds adopt an E configuration around the C=N bond. The molecules are bent at the S atom with C-S -N-N torsion angles of -59.0 (3), 58.0 (2) and -70.2 (1)degrees in (I), (II) and (III), respectively. The sulfonohydrazide 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)degrees 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)degrees in (I), 176.7 (2)degrees in (II) and 175.0 (2)degrees in (III). The 4-nitro-substituted phenylsulfonyl and 2/4-substituted benzylidene rings are inclined to each other by 81.1 (1)degrees in (I), 81.4 (1)degrees in (II) and 74.4 (1)degrees in (III). The compounds show differences in hydrogen-bonding interactions. In the crystal of (I), molecules are linked via N-H center dot center dot center dot O hydrogen bonds, forming C(4) chains along the a-axis direction that are interconnected by weak C-H center dot center dot center dot O hydrogen bonds, generating layers parallel to the ac plane. In the crystal of (II), the amino H atom shows bifurcated N-H center dot center dot center dot 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 center dot center dot center dot O hydrogen bonds, forming a three-dimensional framework. In the crystal of (III), molecules are linked by Ow-H center dot center dot center dot O, N-H center dot center dot center dot Ow and C-H center dot center dot center dot O hydrogen bonds, forming layers lying parallel to the be plane. The fingerprint plots generated for the three compounds show that for (I) and (II) the O center dot center dot center dot H/H center dot center dot center dot O contacts make the largest contributions, while for the parasubstituted compound (III), H center dot center dot center dot H contacts are the major contributors to the Hirshfeld surfaces.

Item Type: Article
Erschienen: 2018
Creators: Salian, Akshatha R. ; Foro, Sabine ; Thimme Gowda, B.
Title: Crystal structures and the Hirshfeld surface analysis of (E)-4-nitro-N′-(o-chloro, o- and p-methylbenzylidene)benzenesulfonohydrazides
Language: English
Abstract:

The crystal structures of (E)-N'-(2-chlorobenzylidene)-4-nitrobenzenesulfonohydrazide, C13H10ClN3O4S (I), (E)-N'-(2-methylbenzylidene)-4-nitrobenzenesulfonohydrazide, C14H13N3O4 S (II), and (E)-N'-(4-methylbenzylidene)-4-nitrobenzenesulfonohydrazide monohydrate, C14H13N3O4S center dot 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 interactions. All three compounds crystallize in the monoclinic crystal system, with space group P2(1) for (I) and P2(1)/c for (II) and (III). Compound (III) crystallizes as a monohydrate. All three compounds adopt an E configuration around the C=N bond. The molecules are bent at the S atom with C-S -N-N torsion angles of -59.0 (3), 58.0 (2) and -70.2 (1)degrees in (I), (II) and (III), respectively. The sulfonohydrazide 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)degrees 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)degrees in (I), 176.7 (2)degrees in (II) and 175.0 (2)degrees in (III). The 4-nitro-substituted phenylsulfonyl and 2/4-substituted benzylidene rings are inclined to each other by 81.1 (1)degrees in (I), 81.4 (1)degrees in (II) and 74.4 (1)degrees in (III). The compounds show differences in hydrogen-bonding interactions. In the crystal of (I), molecules are linked via N-H center dot center dot center dot O hydrogen bonds, forming C(4) chains along the a-axis direction that are interconnected by weak C-H center dot center dot center dot O hydrogen bonds, generating layers parallel to the ac plane. In the crystal of (II), the amino H atom shows bifurcated N-H center dot center dot center dot 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 center dot center dot center dot O hydrogen bonds, forming a three-dimensional framework. In the crystal of (III), molecules are linked by Ow-H center dot center dot center dot O, N-H center dot center dot center dot Ow and C-H center dot center dot center dot O hydrogen bonds, forming layers lying parallel to the be plane. The fingerprint plots generated for the three compounds show that for (I) and (II) the O center dot center dot center dot H/H center dot center dot center dot O contacts make the largest contributions, while for the parasubstituted compound (III), H center dot center dot center dot H contacts are the major contributors to the Hirshfeld surfaces.

Journal or Publication Title: Acta Crystallographica Section E: Crystallographic Communications
Journal volume: 74
Number: 12
Publisher: International Union of Crystallography (IUCr)
Uncontrolled Keywords: Crystal structure, N-(arylidene)-aryl-sulfonohydrazides, hydrogen bonding, ring motif, Hirshfeld surface analysis, fingerprint plots
Divisions: 11 Department of Materials and Earth Sciences
11 Department of Materials and Earth Sciences > Material Science
11 Department of Materials and Earth Sciences > Material Science > Structure Research
Date Deposited: 11 Sep 2020 06:59
DOI: 10.1107/S2056989018015207
Official URL: http://scripts.iucr.org/cgi-bin/paper?S2056989018015207
Additional Information:

ARS thanks the Department of Science and Technology, Government of India, New Delhi, for a research fellowship under its DST-PURSE Program. BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under a UGC-BSR one-time grant to faculty.

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