TU Darmstadt / ULB / TUbiblio

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

Salian, Akshatha R. ; Foro, Sabine ; Thimme Gowda, B. (2018):
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.
In: Acta Crystallographica Section E Crystallographic Communications, 74 (11), pp. 1613-1618. International Union of Crystallography, ISSN 2056-9890,
DOI: 10.1107/S2056989018014500,
[Article]

Abstract

(E)-N'-Benzylidene-4-chlorobenzenesulfonohydrazide, C13H11ClN2O2S, (I), and its ortho- and para-methylsubstituted derivatives, C14H13ClN2O2S, namely (E)-4-chloro-N'-(2-methylbenzylidene)benzenesulfonohydrazide, (II), and (E)-4-chloro-N'-(4-methylbenzylidene)benzenesulfonohydrazide, (III), have been synthesized, characterized spectroscopically and their crystal structures determined to investigate the effect of the substitution site of the benzylidene group on the structural and supramolecular features in these compounds. Compounds (I) and (II) are isotypic while compound (III) is different. All three molecules are bent at the S atom with C-S-N-N torsion angles of -66.0 (3), -66.0 (3) and -58.4 (2)degrees for (I), (II) and (III), respectively. The hydrazone portions of the molecules, S-N-N=C, are slightly twisted from planarity, with a torsion angle of 166.5 (3)degrees in (I), 165.4 (3)degrees in (II) and 157.9 (2)degrees 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)degrees 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 center dot center dot center dot O hydrogen bond links the molecules into chains along [001], which are interconnected by weak intermolecular C-H center dot center dot center dot O interactions, generating layers lying parallel to the bc plane. In the crystal of the para derivative (III), however, the packing is significantly different. Here molecules are linked by 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 then linked by C-Cl center dot center dot center dot pi interactions, forming ribbons propagating along [1 (1) over bar0]. Hirshfeld surface analyses show that the van der Waals interactions constitute the major contribution to the intermolecular interactions in the crystal structures of all three compounds. The fingerprint plots indicate that the H center dot center dot center dot H contacts make the largest contributions to the Hirshfeld surfaces.

Item Type: Article
Erschienen: 2018
Creators: Salian, Akshatha R. ; Foro, Sabine ; Thimme Gowda, B.
Title: 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
Language: English
Abstract:

(E)-N'-Benzylidene-4-chlorobenzenesulfonohydrazide, C13H11ClN2O2S, (I), and its ortho- and para-methylsubstituted derivatives, C14H13ClN2O2S, namely (E)-4-chloro-N'-(2-methylbenzylidene)benzenesulfonohydrazide, (II), and (E)-4-chloro-N'-(4-methylbenzylidene)benzenesulfonohydrazide, (III), have been synthesized, characterized spectroscopically and their crystal structures determined to investigate the effect of the substitution site of the benzylidene group on the structural and supramolecular features in these compounds. Compounds (I) and (II) are isotypic while compound (III) is different. All three molecules are bent at the S atom with C-S-N-N torsion angles of -66.0 (3), -66.0 (3) and -58.4 (2)degrees for (I), (II) and (III), respectively. The hydrazone portions of the molecules, S-N-N=C, are slightly twisted from planarity, with a torsion angle of 166.5 (3)degrees in (I), 165.4 (3)degrees in (II) and 157.9 (2)degrees 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)degrees 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 center dot center dot center dot O hydrogen bond links the molecules into chains along [001], which are interconnected by weak intermolecular C-H center dot center dot center dot O interactions, generating layers lying parallel to the bc plane. In the crystal of the para derivative (III), however, the packing is significantly different. Here molecules are linked by 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 then linked by C-Cl center dot center dot center dot pi interactions, forming ribbons propagating along [1 (1) over bar0]. Hirshfeld surface analyses show that the van der Waals interactions constitute the major contribution to the intermolecular interactions in the crystal structures of all three compounds. The fingerprint plots indicate that the H center dot center dot center dot H contacts make the largest contributions to the Hirshfeld surfaces.

Journal or Publication Title: Acta Crystallographica Section E Crystallographic Communications
Journal volume: 74
Number: 11
Publisher: International Union of Crystallography
Uncontrolled Keywords: crystal structure, benzylidene, benzenesulfonohydrazide, ortho- and para-methyl-substituted derivatives, N-H center dot center dot center dot O hydrogen bonding, C-Cl center dot center dot center dot pi interactions, 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: 14 Sep 2020 05:37
DOI: 10.1107/S2056989018014500
Official URL: https://doi.org/10.1107/S2056989018014500
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.

Export:
Suche nach Titel in: TUfind oder in Google
Send an inquiry Send an inquiry

Options (only for editors)
Show editorial Details Show editorial Details