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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...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
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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. |
format | Text |
id | pubmed-3006709 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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