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(E)-4-Bromo-2-[(2-hydroxy­phen­yl)iminiometh­yl]phenolate

The title compound, C(13)H(10)BrNO(2), crystallizes in a zwitterionic form. The zwitterion exists in a trans configuration about the C=N bond and is almost planar, the dihedral angle between the two benzene rings being 2.29 (9)°. An intra­molecular N—H⋯O hydrogen bond formed between the iminium NH(+...

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Autores principales: Eltayeb, Naser Eltaher, Teoh, Siang Guan, Fun, Hoong-Kun, Chantrapromma, Suchada
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979394/
https://www.ncbi.nlm.nih.gov/pubmed/21579365
http://dx.doi.org/10.1107/S1600536810015230
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author Eltayeb, Naser Eltaher
Teoh, Siang Guan
Fun, Hoong-Kun
Chantrapromma, Suchada
author_facet Eltayeb, Naser Eltaher
Teoh, Siang Guan
Fun, Hoong-Kun
Chantrapromma, Suchada
author_sort Eltayeb, Naser Eltaher
collection PubMed
description The title compound, C(13)H(10)BrNO(2), crystallizes in a zwitterionic form. The zwitterion exists in a trans configuration about the C=N bond and is almost planar, the dihedral angle between the two benzene rings being 2.29 (9)°. An intra­molecular N—H⋯O hydrogen bond formed between the iminium NH(+) and the phenolate O(−) atoms generates an S(6) ring motif. In the crystal, the zwitterions are linked through O—H⋯O hydrogen bonds into chains along [101] and these chains are further connected through C—H⋯Br inter­actions into a two-dimensional network perpendicular to (101). C⋯C [3.572 (3)–3.592 (3) Å] and C⋯Br [3.5633 (19)–3.7339 (18) Å] short contacts are observed. The crystal studied was a twin with twin law [Image: see text]00, 0[Image: see text]0, 001 with a domain ratio of 0.09919 (2):0.90081 (2).
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spelling pubmed-29793942010-12-30 (E)-4-Bromo-2-[(2-hydroxy­phen­yl)iminiometh­yl]phenolate Eltayeb, Naser Eltaher Teoh, Siang Guan Fun, Hoong-Kun Chantrapromma, Suchada Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(13)H(10)BrNO(2), crystallizes in a zwitterionic form. The zwitterion exists in a trans configuration about the C=N bond and is almost planar, the dihedral angle between the two benzene rings being 2.29 (9)°. An intra­molecular N—H⋯O hydrogen bond formed between the iminium NH(+) and the phenolate O(−) atoms generates an S(6) ring motif. In the crystal, the zwitterions are linked through O—H⋯O hydrogen bonds into chains along [101] and these chains are further connected through C—H⋯Br inter­actions into a two-dimensional network perpendicular to (101). C⋯C [3.572 (3)–3.592 (3) Å] and C⋯Br [3.5633 (19)–3.7339 (18) Å] short contacts are observed. The crystal studied was a twin with twin law [Image: see text]00, 0[Image: see text]0, 001 with a domain ratio of 0.09919 (2):0.90081 (2). International Union of Crystallography 2010-05-08 /pmc/articles/PMC2979394/ /pubmed/21579365 http://dx.doi.org/10.1107/S1600536810015230 Text en © Eltayeb et al. 2010 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
Eltayeb, Naser Eltaher
Teoh, Siang Guan
Fun, Hoong-Kun
Chantrapromma, Suchada
(E)-4-Bromo-2-[(2-hydroxy­phen­yl)iminiometh­yl]phenolate
title (E)-4-Bromo-2-[(2-hydroxy­phen­yl)iminiometh­yl]phenolate
title_full (E)-4-Bromo-2-[(2-hydroxy­phen­yl)iminiometh­yl]phenolate
title_fullStr (E)-4-Bromo-2-[(2-hydroxy­phen­yl)iminiometh­yl]phenolate
title_full_unstemmed (E)-4-Bromo-2-[(2-hydroxy­phen­yl)iminiometh­yl]phenolate
title_short (E)-4-Bromo-2-[(2-hydroxy­phen­yl)iminiometh­yl]phenolate
title_sort (e)-4-bromo-2-[(2-hydroxy­phen­yl)iminiometh­yl]phenolate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979394/
https://www.ncbi.nlm.nih.gov/pubmed/21579365
http://dx.doi.org/10.1107/S1600536810015230
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