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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...

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Autores principales: Rodriguez, Mark A., O’Bryan, Greg, Andrzejewski, William J., McElhanon, James R.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
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.
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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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