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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...

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Autores principales: Chetioui, Souheyla, Boudraa, Issam, Bouacida, Sofiane, Bouchoul, Abdelkader, Bouaoud, Salah Eddine
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
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.
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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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