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5-Hydroxy-2-{(E)-[(3-nitrophenyl)iminio]methyl}phenolate
The title compound, C(13)H(10)N(2)O(4), crystallized as the zwitterionic tautomer. As a result, the phenolate C—O(−) bond [1.296 (2) Å] is shorter than a normal Csp (2)—O(H) bond, and the azomethine C=N bond [1.314 (2) Å] is longer than a normal C=N double bond. The molecule is nearly planar, the m...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3435650/ https://www.ncbi.nlm.nih.gov/pubmed/22969523 http://dx.doi.org/10.1107/S1600536812033740 |
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author | Shaheen, Muhammad Ashraf Tahir, M. Nawaz Irfan, Rana Muhammad Iqbal, Shahid Ahmad, Saeed |
author_facet | Shaheen, Muhammad Ashraf Tahir, M. Nawaz Irfan, Rana Muhammad Iqbal, Shahid Ahmad, Saeed |
author_sort | Shaheen, Muhammad Ashraf |
collection | PubMed |
description | The title compound, C(13)H(10)N(2)O(4), crystallized as the zwitterionic tautomer. As a result, the phenolate C—O(−) bond [1.296 (2) Å] is shorter than a normal Csp (2)—O(H) bond, and the azomethine C=N bond [1.314 (2) Å] is longer than a normal C=N double bond. The molecule is nearly planar, the mean plane of the nitro-substituted benzene ring forming dihedral angles of 9.83 (7) and 8.45 (9)° with the other benzene ring and with the nitro group, respectively. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond. In the crystal, strong O—H⋯O hydrogen bonds link the molecules into double-stranded chains along the b-axis direction. Within the chains there are π–π interactions involving the benzene rings of adjacent molecules [centroid–centroid distance = 3.669 (1) Å]. The chains are linked via C—H⋯O hydrogen bonds, forming R (2) (1)(6), R (2) (1)(7) and R (2) (2)(10) ring motifs. |
format | Online Article Text |
id | pubmed-3435650 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-34356502012-09-11 5-Hydroxy-2-{(E)-[(3-nitrophenyl)iminio]methyl}phenolate Shaheen, Muhammad Ashraf Tahir, M. Nawaz Irfan, Rana Muhammad Iqbal, Shahid Ahmad, Saeed Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(13)H(10)N(2)O(4), crystallized as the zwitterionic tautomer. As a result, the phenolate C—O(−) bond [1.296 (2) Å] is shorter than a normal Csp (2)—O(H) bond, and the azomethine C=N bond [1.314 (2) Å] is longer than a normal C=N double bond. The molecule is nearly planar, the mean plane of the nitro-substituted benzene ring forming dihedral angles of 9.83 (7) and 8.45 (9)° with the other benzene ring and with the nitro group, respectively. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond. In the crystal, strong O—H⋯O hydrogen bonds link the molecules into double-stranded chains along the b-axis direction. Within the chains there are π–π interactions involving the benzene rings of adjacent molecules [centroid–centroid distance = 3.669 (1) Å]. The chains are linked via C—H⋯O hydrogen bonds, forming R (2) (1)(6), R (2) (1)(7) and R (2) (2)(10) ring motifs. International Union of Crystallography 2012-08-01 /pmc/articles/PMC3435650/ /pubmed/22969523 http://dx.doi.org/10.1107/S1600536812033740 Text en © Shaheen et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Shaheen, Muhammad Ashraf Tahir, M. Nawaz Irfan, Rana Muhammad Iqbal, Shahid Ahmad, Saeed 5-Hydroxy-2-{(E)-[(3-nitrophenyl)iminio]methyl}phenolate |
title | 5-Hydroxy-2-{(E)-[(3-nitrophenyl)iminio]methyl}phenolate |
title_full | 5-Hydroxy-2-{(E)-[(3-nitrophenyl)iminio]methyl}phenolate |
title_fullStr | 5-Hydroxy-2-{(E)-[(3-nitrophenyl)iminio]methyl}phenolate |
title_full_unstemmed | 5-Hydroxy-2-{(E)-[(3-nitrophenyl)iminio]methyl}phenolate |
title_short | 5-Hydroxy-2-{(E)-[(3-nitrophenyl)iminio]methyl}phenolate |
title_sort | 5-hydroxy-2-{(e)-[(3-nitrophenyl)iminio]methyl}phenolate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3435650/ https://www.ncbi.nlm.nih.gov/pubmed/22969523 http://dx.doi.org/10.1107/S1600536812033740 |
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