(E)-4-Allyl-2-[(2-hydroxy­phen­yl)iminiometh­yl]-6-methoxy­phenolate

The title compound, C(17)H(17)NO(3), crystallizes in a zwitterionic form with cationic iminium and anionic enolate groups. The zwitterion exists in a trans configuration about the C=N bond. The dihedral angle between the two benzene rings is 13.42 (7)°. The meth­oxy group is almost coplanar [C—O—C—C...

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Autores principales: Eltayeb, Naser Eltaher, Teoh, Siang Guan, Chantrapromma, Suchada, Fun, Hoong-Kun
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983958/
https://www.ncbi.nlm.nih.gov/pubmed/21580744
http://dx.doi.org/10.1107/S160053681000838X
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author Eltayeb, Naser Eltaher
Teoh, Siang Guan
Chantrapromma, Suchada
Fun, Hoong-Kun
author_facet Eltayeb, Naser Eltaher
Teoh, Siang Guan
Chantrapromma, Suchada
Fun, Hoong-Kun
author_sort Eltayeb, Naser Eltaher
collection PubMed
description The title compound, C(17)H(17)NO(3), crystallizes in a zwitterionic form with cationic iminium and anionic enolate groups. The zwitterion exists in a trans configuration about the C=N bond. The dihedral angle between the two benzene rings is 13.42 (7)°. The meth­oxy group is almost coplanar [C—O—C—C = 2.1 (2)°] with the attached ring whereas the allyl unit is oriented at a dihedral angle of 67.9 (1)°. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the mol­ecules are linked into zigzag chains along [010] by O—H⋯O hydrogen bonds. In addition, weak C—H⋯π inter­actions are observed.
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spelling pubmed-29839582010-12-30 (E)-4-Allyl-2-[(2-hydroxy­phen­yl)iminiometh­yl]-6-methoxy­phenolate Eltayeb, Naser Eltaher Teoh, Siang Guan Chantrapromma, Suchada Fun, Hoong-Kun Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(17)H(17)NO(3), crystallizes in a zwitterionic form with cationic iminium and anionic enolate groups. The zwitterion exists in a trans configuration about the C=N bond. The dihedral angle between the two benzene rings is 13.42 (7)°. The meth­oxy group is almost coplanar [C—O—C—C = 2.1 (2)°] with the attached ring whereas the allyl unit is oriented at a dihedral angle of 67.9 (1)°. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the mol­ecules are linked into zigzag chains along [010] by O—H⋯O hydrogen bonds. In addition, weak C—H⋯π inter­actions are observed. International Union of Crystallography 2010-03-27 /pmc/articles/PMC2983958/ /pubmed/21580744 http://dx.doi.org/10.1107/S160053681000838X 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
Chantrapromma, Suchada
Fun, Hoong-Kun
(E)-4-Allyl-2-[(2-hydroxy­phen­yl)iminiometh­yl]-6-methoxy­phenolate
title (E)-4-Allyl-2-[(2-hydroxy­phen­yl)iminiometh­yl]-6-methoxy­phenolate
title_full (E)-4-Allyl-2-[(2-hydroxy­phen­yl)iminiometh­yl]-6-methoxy­phenolate
title_fullStr (E)-4-Allyl-2-[(2-hydroxy­phen­yl)iminiometh­yl]-6-methoxy­phenolate
title_full_unstemmed (E)-4-Allyl-2-[(2-hydroxy­phen­yl)iminiometh­yl]-6-methoxy­phenolate
title_short (E)-4-Allyl-2-[(2-hydroxy­phen­yl)iminiometh­yl]-6-methoxy­phenolate
title_sort (e)-4-allyl-2-[(2-hydroxy­phen­yl)iminiometh­yl]-6-methoxy­phenolate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983958/
https://www.ncbi.nlm.nih.gov/pubmed/21580744
http://dx.doi.org/10.1107/S160053681000838X
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AT chantraprommasuchada e4allyl22hydroxyphenyliminiomethyl6methoxyphenolate
AT funhoongkun e4allyl22hydroxyphenyliminiomethyl6methoxyphenolate

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