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2-(6-二乙氨基-3-二乙亚氨基-3H-呫吨-9-基)苯甲酸酯-没食子酸乙酯(1/1)在室温下的重新测定

A redetermination of 2-(6-diethyl-amino-3-diethyl-iminio-3H-xanthen-9-yl)benzoate-ethyl gallate (1/1) at room temperature.

作者信息

Mizuguchi Jin, Sato Kazuyuki

机构信息

Department of Applied Physics, Graduate School of Engineering, Yokohama National University, Tokiwadai 79-5, Hodogaya-ku, Yokohama 240-8501, Japan.

出版信息

Acta Crystallogr Sect E Struct Rep Online. 2009 Mar 6;65(Pt 4):o701-2. doi: 10.1107/S160053680900751X.

Abstract

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-diethyl-amino-3-diethyl-iminio-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 inter-molecular O-H⋯O hydrogen bonds. In a subsequent re-examination of the structure at room temperature, we found the RBB mol-ecule to be disordered with a methyl group of one ethyl substituent of a diethyl-amino 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 diethyl-amino 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.

摘要

标题化合物C(28)H(30)N(2)O(3)·C(9)H(10)O(5)是一种众所周知的2-(6-二乙氨基-3-二乙亚氨基-3H-呫吨-9-基)苯甲酸酯(若丹明B碱,简称为RBB:无色染料)与没食子酸乙酯(EG:显影剂)形成的红色无色配合物。Sekiguchi、Takayama、Gotanda和Sano最近报道了该配合物在室温下的结构[(2007) Chem. Lett. 36, 1010 - 1011]。RBB - EG配合物通过分子间O - H⋯O氢键形成二聚体(RBB⋯EG⋯EG⋯RBB)。在随后对室温下结构的重新研究中,我们发现若丹明B分子无序,在呫吨单元一端的二乙氨基的一个乙基取代基的甲基在两个位置上无序分布[占有率:0.735 (5)/0.265 (5)]。此外,在呫吨残基的另一端,整个二乙氨基取代基(即N原子以及相连的C和H原子)也在两个位置上无序分布,占有率为0.653 (7)/0.347 (7)。这导致了四种若丹明B构象,进而在晶体中形成16种离散的RBB⋯EG⋯EG⋯RBB二聚体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e344/2968829/500236465bd5/e-65-0o701-fig1.jpg

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