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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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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2008
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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. |
format | Text |
id | pubmed-2961781 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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