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A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K

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-xanthen-9-yl)benzoate (rhodamine B base abbreviated to RBB, a leuco dye) with ethyl gallate (EG, developer). The structure of the complex at room temperature has recently...

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Autor principal: Mizuguchi, Jin
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961781/
https://www.ncbi.nlm.nih.gov/pubmed/21202875
http://dx.doi.org/10.1107/S1600536808016528
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author Mizuguchi, Jin
author_facet Mizuguchi, Jin
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-xanthen-9-yl)benzoate (rhodamine B base abbreviated to RBB, a leuco dye) with ethyl gallate (EG, developer). The structure of the complex at room temperature has recently been reported by Sekiguchi, Takayama, Gotanda & Sano [Chem. Lett. (2007 ▶), 36, 1010–1011]. We have found a new phase of the material with two discrete base/developer complexes (RBB-A/EG-A and RBB-B/EG-B) in the asymmetric unit at 93 K. There are no significant differences between the two developer mol­ecules EG-A and EG-B. The lactone ring of RBB is opened in each mol­ecule to form a zwitterionic structure. However, the xanthene system is almost flat in RBB-A (r.m.s. deviation 0.0234 Å) but is less so in RBB-B (r.m.s. deviation 0.1095 Å). Furthermore, the ethyl groups of the xanthene diethyl­amino substituents lie on the same side of the xanthene plane in RBB-A but on opposite sides in RBB-B. Dimeric dye/developer complexes are formed through inter- and intra­molecular O—H⋯O hydrogen bonds and are linked further into dimers by additional O—H⋯O hydrogen bonds involving either EG-A or EG-B developer mol­ecules.
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spelling pubmed-29617812010-12-30 A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K Mizuguchi, Jin 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-xanthen-9-yl)benzoate (rhodamine B base abbreviated to RBB, a leuco dye) with ethyl gallate (EG, developer). The structure of the complex at room temperature has recently been reported by Sekiguchi, Takayama, Gotanda & Sano [Chem. Lett. (2007 ▶), 36, 1010–1011]. We have found a new phase of the material with two discrete base/developer complexes (RBB-A/EG-A and RBB-B/EG-B) in the asymmetric unit at 93 K. There are no significant differences between the two developer mol­ecules EG-A and EG-B. The lactone ring of RBB is opened in each mol­ecule to form a zwitterionic structure. However, the xanthene system is almost flat in RBB-A (r.m.s. deviation 0.0234 Å) but is less so in RBB-B (r.m.s. deviation 0.1095 Å). Furthermore, the ethyl groups of the xanthene diethyl­amino substituents lie on the same side of the xanthene plane in RBB-A but on opposite sides in RBB-B. Dimeric dye/developer complexes are formed through inter- and intra­molecular O—H⋯O hydrogen bonds and are linked further into dimers by additional O—H⋯O hydrogen bonds involving either EG-A or EG-B developer mol­ecules. International Union of Crystallography 2008-06-07 /pmc/articles/PMC2961781/ /pubmed/21202875 http://dx.doi.org/10.1107/S1600536808016528 Text en © Jin Mizuguchi 2008 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
A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K
title A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K
title_full A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K
title_fullStr A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K
title_full_unstemmed A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K
title_short A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl­iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K
title_sort low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl­iminio-3h-xanthen-9-yl)benzoate with ethyl gallate at 93 k
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961781/
https://www.ncbi.nlm.nih.gov/pubmed/21202875
http://dx.doi.org/10.1107/S1600536808016528
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