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Crystal structure and Hirshfeld surface analysis of N,N′-bis(2-nitrophenyl)glutaramide

Salian, Akshatha R. ; Foro, Sabine ; Kumar, S. Madan ; Thimme Gowda, B. (2018):
Crystal structure and Hirshfeld surface analysis of N,N′-bis(2-nitrophenyl)glutaramide.
In: Acta Crystallographica Section E Crystallographic Communications, 74 (10), pp. 1455-1459. International Union of Crystallography, ISSN 2056-9890,
DOI: 10.1107/S2056989018013075,
[Article]

Abstract

The asymmetric unit of the title compound, C17H16N4O6, contains two independent molecules (A and B). The two benzene rings are twisted by an angle of 79.14 (7)degrees in molecule A, whereas, in molecule B, they are inclined by 19.02 (14)degrees. The conformations of the molecules are stabilized by intramolecular N-H center dot center dot center dot O hydrogen bonds between the amide nitrogen atom and the O atom of the ortho-nitro substituent on the phenyl ring, enclosing an S(6) ring motif. In the amide and aliphatic segments, all the N-H, C=O and C-H bonds are anti to each other. In the crystal, the A and B molecules are linked by intermolecular amide-to-amide N-H center dot center dot center dot O hydrogen bonds, resulting in chains running along the b-axis direction. The intermolecular interactions were analysed using Hirshfeld surface analysis. The two-dimensional fingerprint plots of the intermolecular contacts indicate that the major contributions are from H center dot center dot center dot H and O center dot center dot center dot H interactions.

Item Type: Article
Erschienen: 2018
Creators: Salian, Akshatha R. ; Foro, Sabine ; Kumar, S. Madan ; Thimme Gowda, B.
Title: Crystal structure and Hirshfeld surface analysis of N,N′-bis(2-nitrophenyl)glutaramide
Language: English
Abstract:

The asymmetric unit of the title compound, C17H16N4O6, contains two independent molecules (A and B). The two benzene rings are twisted by an angle of 79.14 (7)degrees in molecule A, whereas, in molecule B, they are inclined by 19.02 (14)degrees. The conformations of the molecules are stabilized by intramolecular N-H center dot center dot center dot O hydrogen bonds between the amide nitrogen atom and the O atom of the ortho-nitro substituent on the phenyl ring, enclosing an S(6) ring motif. In the amide and aliphatic segments, all the N-H, C=O and C-H bonds are anti to each other. In the crystal, the A and B molecules are linked by intermolecular amide-to-amide N-H center dot center dot center dot O hydrogen bonds, resulting in chains running along the b-axis direction. The intermolecular interactions were analysed using Hirshfeld surface analysis. The two-dimensional fingerprint plots of the intermolecular contacts indicate that the major contributions are from H center dot center dot center dot H and O center dot center dot center dot H interactions.

Journal or Publication Title: Acta Crystallographica Section E Crystallographic Communications
Journal volume: 74
Number: 10
Publisher: International Union of Crystallography
Uncontrolled Keywords: crystal structure, bis-amides, intermolecular hydrogen bonds, 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 05:44
DOI: 10.1107/S2056989018013075
Official URL: https://doi.org/10.1107/S2056989018013075
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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