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Hydrazinium 2-amino-4-nitrobenzoate dihydrate: crystal structure and Hirshfeld surface analysis
In the anion of the title salt hydrate, H(5)N(2) (+)·C(7)H(5)N(2)O(4) (−)·2H(2)O, the carboxylate and nitro groups lie out of the plane of the benzene ring to which they are bound [dihedral angles = 18.80 (10) and 8.04 (9)°, respectively], and as these groups are conrotatory, the dihedral angle bet...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5382626/ https://www.ncbi.nlm.nih.gov/pubmed/28435725 http://dx.doi.org/10.1107/S2056989017004352 |
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author | Wardell, James L. Jotani, Mukesh M. Tiekink, Edward R. T. |
author_facet | Wardell, James L. Jotani, Mukesh M. Tiekink, Edward R. T. |
author_sort | Wardell, James L. |
collection | PubMed |
description | In the anion of the title salt hydrate, H(5)N(2) (+)·C(7)H(5)N(2)O(4) (−)·2H(2)O, the carboxylate and nitro groups lie out of the plane of the benzene ring to which they are bound [dihedral angles = 18.80 (10) and 8.04 (9)°, respectively], and as these groups are conrotatory, the dihedral angle between them is 26.73 (15)°. An intramolecular amino-N—H⋯O(carboxylate) hydrogen bond is noted. The main feature of the crystal packing is the formation of a supramolecular chain along the b axis, with a zigzag topology, sustained by charge-assisted water-O—H⋯O(carboxylate) hydrogen bonds and comprising alternating twelve-membered {⋯OCO⋯HOH}(2) and eight-membered {⋯O⋯HOH}(2) synthons. Each ammonium-N—H atom forms a charge-assisted hydrogen bond to a water molecule and, in addition, one of these forms a hydrogen bond with a nitro-O atom. The amine-N—H atoms form hydrogen bonds to carboxylate-O and water-O atoms, and the amine N atom accepts a hydrogen bond from an amino-H atom. The hydrogen bonds lead to a three-dimensional architecture. An analysis of the Hirshfeld surface highlights the major contribution of O⋯H/H⋯O hydrogen bonding to the overall surface, i.e. 46.8%, compared with H⋯H contacts (32.4%). |
format | Online Article Text |
id | pubmed-5382626 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-53826262017-04-21 Hydrazinium 2-amino-4-nitrobenzoate dihydrate: crystal structure and Hirshfeld surface analysis Wardell, James L. Jotani, Mukesh M. Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications In the anion of the title salt hydrate, H(5)N(2) (+)·C(7)H(5)N(2)O(4) (−)·2H(2)O, the carboxylate and nitro groups lie out of the plane of the benzene ring to which they are bound [dihedral angles = 18.80 (10) and 8.04 (9)°, respectively], and as these groups are conrotatory, the dihedral angle between them is 26.73 (15)°. An intramolecular amino-N—H⋯O(carboxylate) hydrogen bond is noted. The main feature of the crystal packing is the formation of a supramolecular chain along the b axis, with a zigzag topology, sustained by charge-assisted water-O—H⋯O(carboxylate) hydrogen bonds and comprising alternating twelve-membered {⋯OCO⋯HOH}(2) and eight-membered {⋯O⋯HOH}(2) synthons. Each ammonium-N—H atom forms a charge-assisted hydrogen bond to a water molecule and, in addition, one of these forms a hydrogen bond with a nitro-O atom. The amine-N—H atoms form hydrogen bonds to carboxylate-O and water-O atoms, and the amine N atom accepts a hydrogen bond from an amino-H atom. The hydrogen bonds lead to a three-dimensional architecture. An analysis of the Hirshfeld surface highlights the major contribution of O⋯H/H⋯O hydrogen bonding to the overall surface, i.e. 46.8%, compared with H⋯H contacts (32.4%). International Union of Crystallography 2017-03-24 /pmc/articles/PMC5382626/ /pubmed/28435725 http://dx.doi.org/10.1107/S2056989017004352 Text en © Wardell et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Wardell, James L. Jotani, Mukesh M. Tiekink, Edward R. T. Hydrazinium 2-amino-4-nitrobenzoate dihydrate: crystal structure and Hirshfeld surface analysis |
title | Hydrazinium 2-amino-4-nitrobenzoate dihydrate: crystal structure and Hirshfeld surface analysis |
title_full | Hydrazinium 2-amino-4-nitrobenzoate dihydrate: crystal structure and Hirshfeld surface analysis |
title_fullStr | Hydrazinium 2-amino-4-nitrobenzoate dihydrate: crystal structure and Hirshfeld surface analysis |
title_full_unstemmed | Hydrazinium 2-amino-4-nitrobenzoate dihydrate: crystal structure and Hirshfeld surface analysis |
title_short | Hydrazinium 2-amino-4-nitrobenzoate dihydrate: crystal structure and Hirshfeld surface analysis |
title_sort | hydrazinium 2-amino-4-nitrobenzoate dihydrate: crystal structure and hirshfeld surface analysis |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5382626/ https://www.ncbi.nlm.nih.gov/pubmed/28435725 http://dx.doi.org/10.1107/S2056989017004352 |
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