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A redetermination of 2-(6-diethyl­amino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate–ethyl gallate (1/1) at room temperature

The title compound, C(28)H(30)N(2)O(3)·C(9)H(10)O(5), is a well known red leuco complex of 2-(6-diethyl­amino-3-diethyl­iminio-3H-xanthene-9-yl)benzoate (rhodamine B base abbreviated to RBB: leuco dye) with ethyl gallate (EG: developer). The structure of the complex at room temperature has recently...

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Autores principales: Mizuguchi, Jin, Sato, Kazuyuki
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968829/
https://www.ncbi.nlm.nih.gov/pubmed/21582440
http://dx.doi.org/10.1107/S160053680900751X
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author Mizuguchi, Jin
Sato, Kazuyuki
author_facet Mizuguchi, Jin
Sato, Kazuyuki
author_sort Mizuguchi, Jin
collection PubMed
description The title compound, C(28)H(30)N(2)O(3)·C(9)H(10)O(5), is a well known red leuco complex of 2-(6-diethyl­amino-3-diethyl­iminio-3H-xanthene-9-yl)benzoate (rhodamine B base abbreviated to RBB: leuco dye) with ethyl gallate (EG: developer). The structure of the complex at room temperature has recently been reported by Sekiguchi, Takayama, Gotanda & Sano [(2007) Chem. Lett. 36, 1010–1011]. The RBB–EG complex forms a dimer (RBB⋯EG⋯EG⋯RBB) through inter­molecular O—H⋯O hydrogen bonds. In a subsequent re-examination of the structure at room temperature, we found the RBB mol­ecule to be disordered with a methyl group of one ethyl substituent of a diethyl­amino group at one extremity of the xanthene unit disordered over two positions [occupancies: 0.735 (5)/0.265 (5)]. Furthermore, at the other end of the xanthene residue, the entire diethyl­amino substituent (i.e. the N atom and the associated C and H atoms) was also disordered over two sites with occupancies 0.653 (7)/0.347 (7). This leads to four kinds of RBB conformations, which, in turn, results in the formation of 16 discrete RBB⋯EG⋯EG⋯RBB dimers in the crystal.
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spelling pubmed-29688292010-12-30 A redetermination of 2-(6-diethyl­amino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate–ethyl gallate (1/1) at room temperature Mizuguchi, Jin Sato, Kazuyuki Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(28)H(30)N(2)O(3)·C(9)H(10)O(5), is a well known red leuco complex of 2-(6-diethyl­amino-3-diethyl­iminio-3H-xanthene-9-yl)benzoate (rhodamine B base abbreviated to RBB: leuco dye) with ethyl gallate (EG: developer). The structure of the complex at room temperature has recently been reported by Sekiguchi, Takayama, Gotanda & Sano [(2007) Chem. Lett. 36, 1010–1011]. The RBB–EG complex forms a dimer (RBB⋯EG⋯EG⋯RBB) through inter­molecular O—H⋯O hydrogen bonds. In a subsequent re-examination of the structure at room temperature, we found the RBB mol­ecule to be disordered with a methyl group of one ethyl substituent of a diethyl­amino group at one extremity of the xanthene unit disordered over two positions [occupancies: 0.735 (5)/0.265 (5)]. Furthermore, at the other end of the xanthene residue, the entire diethyl­amino substituent (i.e. the N atom and the associated C and H atoms) was also disordered over two sites with occupancies 0.653 (7)/0.347 (7). This leads to four kinds of RBB conformations, which, in turn, results in the formation of 16 discrete RBB⋯EG⋯EG⋯RBB dimers in the crystal. International Union of Crystallography 2009-03-06 /pmc/articles/PMC2968829/ /pubmed/21582440 http://dx.doi.org/10.1107/S160053680900751X Text en © Mizuguchi and Sato 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
Mizuguchi, Jin
Sato, Kazuyuki
A redetermination of 2-(6-diethyl­amino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate–ethyl gallate (1/1) at room temperature
title A redetermination of 2-(6-diethyl­amino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate–ethyl gallate (1/1) at room temperature
title_full A redetermination of 2-(6-diethyl­amino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate–ethyl gallate (1/1) at room temperature
title_fullStr A redetermination of 2-(6-diethyl­amino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate–ethyl gallate (1/1) at room temperature
title_full_unstemmed A redetermination of 2-(6-diethyl­amino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate–ethyl gallate (1/1) at room temperature
title_short A redetermination of 2-(6-diethyl­amino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate–ethyl gallate (1/1) at room temperature
title_sort redetermination of 2-(6-diethyl­amino-3-diethyl­iminio-3h-xanthen-9-yl)benzoate–ethyl gallate (1/1) at room temperature
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968829/
https://www.ncbi.nlm.nih.gov/pubmed/21582440
http://dx.doi.org/10.1107/S160053680900751X
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