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

Salian, Akshatha R. ; Foro, Sabine ; Thimme Gowda, B. (2018):
Crystal structure and Hirshfeld surface analysis of two (E)-N′-(para-substituted benzylidene) 4-chlorobenzenesulfonohydrazides.
In: Acta Crystallographica Section E: Crystallographic Communications, 74 (12), pp. 1808-1814. International Union of Crystallography (IUCr), ISSN 2056-9890,
DOI: 10.1107/S205698901801592X,
[Article]

Abstract

Two (E)-N'-(p-substituted benzylidene)-4-chlorobenzenesulfonohydrazides, namely, (E)-4-chloro-N'-(4-chlorobenzylidene)benzenesulfonohydrazide, C13H10Cl2N2O2S, (I), and (E)-4-chloro-N'-(4-nitrobenzylidene)benzenesulfonohydrazide, 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 molecules [(IIA) and IIB)] in the asymmetric unit. In both compounds, the configuration around the C=N bond is E. The molecules are twisted at the S atom with C-S-N-N torsion angles of -62.4 (2)degrees in (I), and -46.8 (2)degrees and 56.8 (2)degrees in the molecules A and B of (II). The 4-chlorophenylsulfonyl and 4-substituted benzylidene rings form dihedral angles of 81.0 (1)degrees in (I), 75.9 (1)degrees in (IIA) and 73.4 (1)degrees in (IIB). In the crystal of (I), molecules are linked via pairs of N-H center dot center dot center dot O hydrogen bonds, forming inversion dimers with an R-2(2)(8) ring motif. The dimers are linked by C-Cl center dot center dot center dot pi interactions, forming a threedimensional structure. In the crystal of (II), molecules are linked by C-H center dot center dot center dot pi interactions and N-H center dot center dot center dot O hydrogen bonds, forming A B A B chains along the c-axis direction. The chains are linked via C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions, forming layers parallel to the be plane. Two-dimensional fingerprint plots show that the most significant contacts contributing to the Hirshfeld surface for (I) are H center dot center dot center dot H contacts (26.6%), followed by Cl center dot center dot center dot H/H center dot center dot center dot Cl (21.3%), O center dot center dot center dot H/H center dot center dot center dot O (15.5%) and Cl center dot center dot center dot C/C center dot center dot center dot Cl (10.7%), while for (II) the O center dot center dot center dot H/H center dot center dot center dot O contacts are dominant, with a contribution of 34.8%, followed by H center dot center dot center dot H (15.2%), C center dot center dot center dot H/H center dot center dot center dot C (14.0%) and Cl center dot center dot center dot H/H center dot center dot center dot Cl (10.0%) contacts.

Item Type: Article
Erschienen: 2018
Creators: Salian, Akshatha R. ; Foro, Sabine ; Thimme Gowda, B.
Title: Crystal structure and Hirshfeld surface analysis of two (E)-N′-(para-substituted benzylidene) 4-chlorobenzenesulfonohydrazides
Language: English
Abstract:

Two (E)-N'-(p-substituted benzylidene)-4-chlorobenzenesulfonohydrazides, namely, (E)-4-chloro-N'-(4-chlorobenzylidene)benzenesulfonohydrazide, C13H10Cl2N2O2S, (I), and (E)-4-chloro-N'-(4-nitrobenzylidene)benzenesulfonohydrazide, 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 molecules [(IIA) and IIB)] in the asymmetric unit. In both compounds, the configuration around the C=N bond is E. The molecules are twisted at the S atom with C-S-N-N torsion angles of -62.4 (2)degrees in (I), and -46.8 (2)degrees and 56.8 (2)degrees in the molecules A and B of (II). The 4-chlorophenylsulfonyl and 4-substituted benzylidene rings form dihedral angles of 81.0 (1)degrees in (I), 75.9 (1)degrees in (IIA) and 73.4 (1)degrees in (IIB). In the crystal of (I), molecules are linked via pairs of N-H center dot center dot center dot O hydrogen bonds, forming inversion dimers with an R-2(2)(8) ring motif. The dimers are linked by C-Cl center dot center dot center dot pi interactions, forming a threedimensional structure. In the crystal of (II), molecules are linked by C-H center dot center dot center dot pi interactions and N-H center dot center dot center dot O hydrogen bonds, forming A B A B chains along the c-axis direction. The chains are linked via C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions, forming layers parallel to the be plane. Two-dimensional fingerprint plots show that the most significant contacts contributing to the Hirshfeld surface for (I) are H center dot center dot center dot H contacts (26.6%), followed by Cl center dot center dot center dot H/H center dot center dot center dot Cl (21.3%), O center dot center dot center dot H/H center dot center dot center dot O (15.5%) and Cl center dot center dot center dot C/C center dot center dot center dot Cl (10.7%), while for (II) the O center dot center dot center dot H/H center dot center dot center dot O contacts are dominant, with a contribution of 34.8%, followed by H center dot center dot center dot H (15.2%), C center dot center dot center dot H/H center dot center dot center dot C (14.0%) and Cl center dot center dot center dot H/H center dot center dot center dot Cl (10.0%) contacts.

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, hydrazones, N '-(arylidene)arylsulfonohydrazides, hydrogen bonding, graph-set 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 07:02
DOI: 10.1107/S205698901801592X
Official URL: http://scripts.iucr.org/cgi-bin/paper?S205698901801592X
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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