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Comparison of the crystal structures and Hirshfeld surface analysis of five N-(4-methylbenzenesulfonyl)glycine hydrazone derivatives

Purandara, H. ; Foro, Sabine ; Thimme Gowda, B. (2018):
Comparison of the crystal structures and Hirshfeld surface analysis of five N-(4-methylbenzenesulfonyl)glycine hydrazone derivatives.
In: Acta Crystallographica Section C Structural Chemistry, 74 (11), pp. 1553-1560. International Union of Crystallography, ISSN 2053-2296,
DOI: 10.1107/S2053229618014420,
[Article]

Abstract

The crystal structures of N-(4-methylbenzenesulfonyl) glycine hydrazone and four derivatives with four different substituents have been investigated, namely, (E)-N-{2-[2-(benzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H17N3O3S, (I), (E)-N-{2-[2-(4-bromobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16BrN3O3S, (II), (E)-N-{2-[2-(4-chlorobenzylidene) hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16ClN3O3S, (III), (E)-N-(2-{2-[4-(dimethylamino)benzylidene]hydrazinyl}-2-oxoethyl)-4-methylbenzenesulfonamide, C18H22N4O3S, (IV), and (E)-N-{2-[2-(4-methoxybenzylidene) hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C17H19N3O4S, (V). The molecules in all five crystal structures show similar conformations and hydrogen-bonding patterns. The central part of the molecule, i.e. C-C-N-N=C, is almost linear in all the structures, with the C-C-N-N torsion angles ranging from -178.3 (1) to -180.0 (2)degrees and the C-N-N=C torsion angles ranging from -178.5 (4) to -179.8 (3)degrees. The conformation of the N-H and C=O bonds in the amide group of the hydrazone part is syn in all the compounds. In all the structures, sulfonamide and hydrazone dimers with R-2(2) (8) ring motifs are observed, which are further augmented by C-H center dot center dot center dot O interactions. A common feature of each of (I)-(V) is the formation of sulfonamide and hydrazone dimers with an R-2(2) (8) ring motif. Hirshfeld surface analyses gave fingerprint plots for H center dot center dot center dot H, O center dot center dot center dot H/H center dot center dot center dot O, N center dot center dot center dot H/H center dot center dot center dot N, C center dot center dot center dot H/H center dot center dot center dot C and other contacts. The H center dot center dot center dot H contacts show large surfaces, whereas the O center dot center dot center dot H plots show the presence of O center dot center dot center dot H/O center dot center dot center dot H contacts with the two characteristic long sharp spikes.

Item Type: Article
Erschienen: 2018
Creators: Purandara, H. ; Foro, Sabine ; Thimme Gowda, B.
Title: Comparison of the crystal structures and Hirshfeld surface analysis of five N-(4-methylbenzenesulfonyl)glycine hydrazone derivatives
Language: English
Abstract:

The crystal structures of N-(4-methylbenzenesulfonyl) glycine hydrazone and four derivatives with four different substituents have been investigated, namely, (E)-N-{2-[2-(benzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H17N3O3S, (I), (E)-N-{2-[2-(4-bromobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16BrN3O3S, (II), (E)-N-{2-[2-(4-chlorobenzylidene) hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16ClN3O3S, (III), (E)-N-(2-{2-[4-(dimethylamino)benzylidene]hydrazinyl}-2-oxoethyl)-4-methylbenzenesulfonamide, C18H22N4O3S, (IV), and (E)-N-{2-[2-(4-methoxybenzylidene) hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C17H19N3O4S, (V). The molecules in all five crystal structures show similar conformations and hydrogen-bonding patterns. The central part of the molecule, i.e. C-C-N-N=C, is almost linear in all the structures, with the C-C-N-N torsion angles ranging from -178.3 (1) to -180.0 (2)degrees and the C-N-N=C torsion angles ranging from -178.5 (4) to -179.8 (3)degrees. The conformation of the N-H and C=O bonds in the amide group of the hydrazone part is syn in all the compounds. In all the structures, sulfonamide and hydrazone dimers with R-2(2) (8) ring motifs are observed, which are further augmented by C-H center dot center dot center dot O interactions. A common feature of each of (I)-(V) is the formation of sulfonamide and hydrazone dimers with an R-2(2) (8) ring motif. Hirshfeld surface analyses gave fingerprint plots for H center dot center dot center dot H, O center dot center dot center dot H/H center dot center dot center dot O, N center dot center dot center dot H/H center dot center dot center dot N, C center dot center dot center dot H/H center dot center dot center dot C and other contacts. The H center dot center dot center dot H contacts show large surfaces, whereas the O center dot center dot center dot H plots show the presence of O center dot center dot center dot H/O center dot center dot center dot H contacts with the two characteristic long sharp spikes.

Journal or Publication Title: Acta Crystallographica Section C Structural Chemistry
Journal volume: 74
Number: 11
Publisher: International Union of Crystallography
Uncontrolled Keywords: N-acylhydrazone derivatives, crystal structure, conformation, hydrogen-bond interaction, ring motif, Hirshfeld surface analysis
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 05:33
DOI: 10.1107/S2053229618014420
Official URL: https://doi.org/10.1107/S2053229618014420
Additional Information:

HP thanks the Department of Science and Technology, Government of India, New Delhi, for a research fellowship under its INSPIRE 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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