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

The title compound, C(13)H(11)NO(3), crystallizes in a zwitterionic form and has a trans configuration about the C=N bond. The mol­ecule is almost planar, the dihedral angle between the two benzene rings being 4.32 (8)°. The two hy­droxy substit­uents are coplanar with each of their attached benzene...

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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/PMC3006709/
https://www.ncbi.nlm.nih.gov/pubmed/21587785
http://dx.doi.org/10.1107/S1600536810020295
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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(11)NO(3), crystallizes in a zwitterionic form and has a trans configuration about the C=N bond. The mol­ecule is almost planar, the dihedral angle between the two benzene rings being 4.32 (8)°. The two hy­droxy substit­uents are coplanar with each of their attached benzene rings [r.m.s. deviations of 0.0053 (2) and 0.0052 (2) Å]. An intra­molecular N—H⋯O hydrogen bond formed between the iminium N and the phenolate O atom generates an S(6) ring motif. In the crystal, the mol­ecules are linked through O—H⋯O hydrogen bonds into chains along [110]. Two neighbouring chains are further connected through O—H⋯O hydrogen bonds in an anti­parallel manner. π–π inter­actions are also observed, with centroid–centroid distances of 3.7115 (19) and 3.743 (2) Å.
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spelling pubmed-30067092010-12-30 (E)-4-Hy­droxy-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(11)NO(3), crystallizes in a zwitterionic form and has a trans configuration about the C=N bond. The mol­ecule is almost planar, the dihedral angle between the two benzene rings being 4.32 (8)°. The two hy­droxy substit­uents are coplanar with each of their attached benzene rings [r.m.s. deviations of 0.0053 (2) and 0.0052 (2) Å]. An intra­molecular N—H⋯O hydrogen bond formed between the iminium N and the phenolate O atom generates an S(6) ring motif. In the crystal, the mol­ecules are linked through O—H⋯O hydrogen bonds into chains along [110]. Two neighbouring chains are further connected through O—H⋯O hydrogen bonds in an anti­parallel manner. π–π inter­actions are also observed, with centroid–centroid distances of 3.7115 (19) and 3.743 (2) Å. International Union of Crystallography 2010-06-05 /pmc/articles/PMC3006709/ /pubmed/21587785 http://dx.doi.org/10.1107/S1600536810020295 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-Hy­droxy-2-[(2-hy­droxy­phen­yl)iminiometh­yl]phenolate
title (E)-4-Hy­droxy-2-[(2-hy­droxy­phen­yl)iminiometh­yl]phenolate
title_full (E)-4-Hy­droxy-2-[(2-hy­droxy­phen­yl)iminiometh­yl]phenolate
title_fullStr (E)-4-Hy­droxy-2-[(2-hy­droxy­phen­yl)iminiometh­yl]phenolate
title_full_unstemmed (E)-4-Hy­droxy-2-[(2-hy­droxy­phen­yl)iminiometh­yl]phenolate
title_short (E)-4-Hy­droxy-2-[(2-hy­droxy­phen­yl)iminiometh­yl]phenolate
title_sort (e)-4-hy­droxy-2-[(2-hy­droxy­phen­yl)iminiometh­yl]phenolate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3006709/
https://www.ncbi.nlm.nih.gov/pubmed/21587785
http://dx.doi.org/10.1107/S1600536810020295
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