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1-[(E)-2-(2-Hydroxy-5-methylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate
The title zwitterion, C(17)H(14)N(2)O(2), crystallizes with two independent molecules in the asymmetric unit, both of which are approximately planar, the dihedral angles between the benzene ring and the naphthalene ring system being 4.39 (12)° in one molecule and 5.83 (12)° in the other, and show...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3793808/ https://www.ncbi.nlm.nih.gov/pubmed/24109395 http://dx.doi.org/10.1107/S160053681302014X |
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author | Chetioui, Souheyla Boudraa, Issam Bouacida, Sofiane Bouchoul, Abdelkader Bouaoud, Salah Eddine |
author_facet | Chetioui, Souheyla Boudraa, Issam Bouacida, Sofiane Bouchoul, Abdelkader Bouaoud, Salah Eddine |
author_sort | Chetioui, Souheyla |
collection | PubMed |
description | The title zwitterion, C(17)H(14)N(2)O(2), crystallizes with two independent molecules in the asymmetric unit, both of which are approximately planar, the dihedral angles between the benzene ring and the naphthalene ring system being 4.39 (12)° in one molecule and 5.83 (12)° in the other, and show an E conformation with respect to the azo double bond. An intramolecular N—H⋯O hydrogen bond in each molecule helps to establish their near planar conformation. In the crystal, molecules are linked through O—H⋯O hydrogen bonds into infinite chains running along the a-axis direction. In addition, the chains are stacked along the b axis via π–π interactions between the benzene and the naphthalene rings of adjacent molecules, the centroid–centroid distances being 3.722 (3) and 3.823 (4) Å. |
format | Online Article Text |
id | pubmed-3793808 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-37938082013-10-09 1-[(E)-2-(2-Hydroxy-5-methylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate Chetioui, Souheyla Boudraa, Issam Bouacida, Sofiane Bouchoul, Abdelkader Bouaoud, Salah Eddine Acta Crystallogr Sect E Struct Rep Online Organic Papers The title zwitterion, C(17)H(14)N(2)O(2), crystallizes with two independent molecules in the asymmetric unit, both of which are approximately planar, the dihedral angles between the benzene ring and the naphthalene ring system being 4.39 (12)° in one molecule and 5.83 (12)° in the other, and show an E conformation with respect to the azo double bond. An intramolecular N—H⋯O hydrogen bond in each molecule helps to establish their near planar conformation. In the crystal, molecules are linked through O—H⋯O hydrogen bonds into infinite chains running along the a-axis direction. In addition, the chains are stacked along the b axis via π–π interactions between the benzene and the naphthalene rings of adjacent molecules, the centroid–centroid distances being 3.722 (3) and 3.823 (4) Å. International Union of Crystallography 2013-07-27 /pmc/articles/PMC3793808/ /pubmed/24109395 http://dx.doi.org/10.1107/S160053681302014X Text en © Chetioui et al. 2013 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 Chetioui, Souheyla Boudraa, Issam Bouacida, Sofiane Bouchoul, Abdelkader Bouaoud, Salah Eddine 1-[(E)-2-(2-Hydroxy-5-methylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate |
title | 1-[(E)-2-(2-Hydroxy-5-methylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate |
title_full | 1-[(E)-2-(2-Hydroxy-5-methylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate |
title_fullStr | 1-[(E)-2-(2-Hydroxy-5-methylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate |
title_full_unstemmed | 1-[(E)-2-(2-Hydroxy-5-methylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate |
title_short | 1-[(E)-2-(2-Hydroxy-5-methylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate |
title_sort | 1-[(e)-2-(2-hydroxy-5-methylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3793808/ https://www.ncbi.nlm.nih.gov/pubmed/24109395 http://dx.doi.org/10.1107/S160053681302014X |
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