NDLI: Unusual hydrate stabilization in the two-dimensional layered structure of quinacrinium bis(2-carboxy-4,5-dichlorobenzoate) tetrahydrate, a proton-transfer compound of the drug quinacrine

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Unusual hydrate stabilization in the two-dimensional layered structure of quinacrinium bis(2-carboxy-4,5-dichlorobenzoate) tetrahydrate, a proton-transfer compound of the drug quinacrine

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Unusual hydrate stabilization in the two-dimensional layered structure of quinacrinium bis(2-carboxy-4,5-dichlorobenzoate) tetrahydrate, a proton-transfer compound of the drug quinacrine

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Smith, Graham Wermuth, Urs D. Sagatys, Dalius S.
Description	Country affiliation: Australia Author Affiliation: Smith G ( School of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane 4001, Australia. g.smith@qut.edu.au)
Abstract	The crystal structure of the hydrated proton-transfer compound of the drug quinacrine [ rac- N'-(6-chloro-2-methoxyacridin-9-yl)- N, N-diethylpentane-1,4-diamine] with 4,5-dichlorophthalic acid, C $_{23}H$ $_{32}ClN$ $_{3}O$ $^{2+}·2C$ $_{8}H$ $_{3}Cl$ $_{2}O$ $_{4}$ $^{-}·4H$ $_{2}O,$ has been determined at 200 K. The four labile water molecules of solvation in the structure form discrete O-H O-H hydrogen-bonded chains parallel to the quinacrine side chain, the two N-H groups of which act as hydrogen-bond donors for two of the water acceptor molecules. The other water molecules, as well as the acridinium H atom, also form hydrogen bonds with the two anion species and extend the structure into two-dimensional sheets. Between these sheets there are also weak cation-anion and anion-anion - aromatic ring interactions. This structure represents the third example of a simple quinacrine derivative for which structural data are available but differs from the other two in that it is unstable in the X-ray beam due to efflorescence, probably associated with the destruction of the unusual four-membered water chain structures.
File Format	HTM / HTML
e-ISSN	20532296
Journal	Acta Crystallographica Section C Crystal Structure Communications
Issue Number	Pt 4
Volume Number	65
Language	English
Publisher	IUCr/Wiley
Publisher Date	2009-04-01
Publisher Place	United States
Access Restriction	Open
Subject Keyword	Discipline Analytical Chemistry Discipline Crystallography Antimalarials Chemistry Chlorobenzoates Protons Quinacrine Crystallography, X-ray Hydrogen Bonding Molecular Structure Research Support, Non-u.s. Gov't
Content Type	Text
Resource Type	Article

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