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2-{(E)-[1-(2-Hydroxyethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl]vinyl}-6-hydroxymethyl-4-nitrophenolate dihydrate
The title merocyanine-type molecule, C(21)H(22)N(2)O(5)·2H(2)O, crystallizes in a zwitterionic form and has an E configuration at the styryl C=C bond. The styryl part of the molecule and the indolium ring are slightly twisted and form a dihedral angle of 13.4 (1)°. The 1.274 (3) Å C—O bond length...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977230/ https://www.ncbi.nlm.nih.gov/pubmed/21583596 http://dx.doi.org/10.1107/S1600536809027238 |
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author | Rodriguez, Mark A. O’Bryan, Greg Andrzejewski, William J. McElhanon, James R. |
author_facet | Rodriguez, Mark A. O’Bryan, Greg Andrzejewski, William J. McElhanon, James R. |
author_sort | Rodriguez, Mark A. |
collection | PubMed |
description | The title merocyanine-type molecule, C(21)H(22)N(2)O(5)·2H(2)O, crystallizes in a zwitterionic form and has an E configuration at the styryl C=C bond. The styryl part of the molecule and the indolium ring are slightly twisted and form a dihedral angle of 13.4 (1)°. The 1.274 (3) Å C—O bond length in the phenolate fragment is the longest among similar molecules. Hydrogen bonds between solvent water molecules, two hydroxyl groups and the phenolate O atom dictate the packing arrangement of molecules in the crystal and join the molecules into a two-dimensional polymeric network which propagates parallel to (001). Four water molecules and four hydroxy groups form a centrosymmetric homodromic cyclic motif of O—H⋯O hydrogen bonds. Another cyclic centrosymmetric motif is generated by four water molecules and two phenolate O atoms. |
format | Text |
id | pubmed-2977230 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29772302010-12-30 2-{(E)-[1-(2-Hydroxyethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl]vinyl}-6-hydroxymethyl-4-nitrophenolate dihydrate Rodriguez, Mark A. O’Bryan, Greg Andrzejewski, William J. McElhanon, James R. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title merocyanine-type molecule, C(21)H(22)N(2)O(5)·2H(2)O, crystallizes in a zwitterionic form and has an E configuration at the styryl C=C bond. The styryl part of the molecule and the indolium ring are slightly twisted and form a dihedral angle of 13.4 (1)°. The 1.274 (3) Å C—O bond length in the phenolate fragment is the longest among similar molecules. Hydrogen bonds between solvent water molecules, two hydroxyl groups and the phenolate O atom dictate the packing arrangement of molecules in the crystal and join the molecules into a two-dimensional polymeric network which propagates parallel to (001). Four water molecules and four hydroxy groups form a centrosymmetric homodromic cyclic motif of O—H⋯O hydrogen bonds. Another cyclic centrosymmetric motif is generated by four water molecules and two phenolate O atoms. International Union of Crystallography 2009-07-18 /pmc/articles/PMC2977230/ /pubmed/21583596 http://dx.doi.org/10.1107/S1600536809027238 Text en © Rodriguez et al. 2009 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 Rodriguez, Mark A. O’Bryan, Greg Andrzejewski, William J. McElhanon, James R. 2-{(E)-[1-(2-Hydroxyethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl]vinyl}-6-hydroxymethyl-4-nitrophenolate dihydrate |
title | 2-{(E)-[1-(2-Hydroxyethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl]vinyl}-6-hydroxymethyl-4-nitrophenolate dihydrate |
title_full | 2-{(E)-[1-(2-Hydroxyethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl]vinyl}-6-hydroxymethyl-4-nitrophenolate dihydrate |
title_fullStr | 2-{(E)-[1-(2-Hydroxyethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl]vinyl}-6-hydroxymethyl-4-nitrophenolate dihydrate |
title_full_unstemmed | 2-{(E)-[1-(2-Hydroxyethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl]vinyl}-6-hydroxymethyl-4-nitrophenolate dihydrate |
title_short | 2-{(E)-[1-(2-Hydroxyethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl]vinyl}-6-hydroxymethyl-4-nitrophenolate dihydrate |
title_sort | 2-{(e)-[1-(2-hydroxyethyl)-3,3-dimethyl-3h-indol-1-ium-2-yl]vinyl}-6-hydroxymethyl-4-nitrophenolate dihydrate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977230/ https://www.ncbi.nlm.nih.gov/pubmed/21583596 http://dx.doi.org/10.1107/S1600536809027238 |
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