Hydrate stabilization in the three-dimensional hydrogen-bonded structure of the brucinium compound, bis(2,3-dimethoxy-10-oxostrychnidinium) biphenyl-4,4'-disulfonate hexahydrate

G Smith; U D Wermuth; David James Young

doi:10.1007/s10870-010-9689-7

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Hydrate stabilization in the three-dimensional hydrogen-bonded structure of the brucinium compound, bis(2,3-dimethoxy-10-oxostrychnidinium) biphenyl-4,4'-disulfonate hexahydrate

Journal article

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Hydrate stabilization in the three-dimensional hydrogen-bonded structure of the brucinium compound, bis(2,3-dimethoxy-10-oxostrychnidinium) biphenyl-4,4'-disulfonate hexahydrate

G Smith, U D Wermuth and David James Young

Journal of Chemical Crystallography, Vol.40(6), pp.520-525

2010

DOI: https://doi.org/10.1007/s10870-010-9689-7

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Abstract

brucine

biphenyl-4,4′-disulfonate dianions

proton-transfer compounds

crystal structure

hydrogen bonding

The crystal structure of the 2:1 proton-transfer compound of brucine with biphenyl-4,40-disulfonate, bis(2, 3-dimethoxy-10-oxostrychnidinium) biphenyl-4,4'-disulfonate hexahydrate (1) has been determined at 173 K. Crystals are monoclinic, space group P21 with Z = 2 in a cell with a = 8.0314(2), b = 29.3062(9), c = 12.2625(3) Ã… β = 101.331(2)°. The crystallographic asymmetric unit comprises two brucinium cations, a biphenyl-4,40-disulfonate dianion and six water molecules of solvation. The brucinium cations form a variant of the common undulating and overlapping head-to-tail sheet sub-structure. The sulfonate dianions are also linked head-to-tail by hydrogen bonds into parallel zig-zag chains through clusters of six water molecules of which five are inter-associated, featuring conjoint cyclic eight-membered hydrogen-bonded rings [graph sets R3 3 (8) and R43 (8)], comprising four of the water molecules and closed by sulfonate O acceptors. These chain structures occupy the cavities between the brucinium cation sheets and are linked to them peripherally through both brucine N+-Hâ‹¯Osulfonate and Ocarbonylâ‹¯H-Owater to sulfonate O bridging hydrogen bonds, forming an overall three-dimensional framework structure. This structure determination confirms the importance of water in the stabilization of certain brucine compounds which have inherent crystal instability. © Springer Science+Business Media, LLC 2010.

Details

Title: Hydrate stabilization in the three-dimensional hydrogen-bonded structure of the brucinium compound, bis(2,3-dimethoxy-10-oxostrychnidinium) biphenyl-4,4'-disulfonate hexahydrate
Authors: G Smith (Author) - Queensland University of Technology
U D Wermuth (Author) - Queensland University of Technology
David James Young (Author) - Griffith University
Publication details: Journal of Chemical Crystallography, Vol.40(6), pp.520-525
Publisher: Springer New York LLC
Date published: 2010
DOI: 10.1007/s10870-010-9689-7
ISSN: 1074-1542
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99449566202621
Output Type: Journal article

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Collaboration types: Domestic collaboration
Web Of Science research areas: Crystallography; Spectroscopy

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