Novel, predicted patterns of supramolecular self-assembly, afforded by tetrameric R-4(4)(12) rings of C-2 symmetry in the crystal structures of 2-hydroxy-1-cyclopentanecarboxylic acid, 2-hydroxy-1-cyclohexanecarboxylic acid and 2-hydroxy-1-cycloheptanecarboxylic acid

Kalman, A., Fabian, L., Argay, G., Bernath, G. and Gyarmati, Z. (2002) Novel, predicted patterns of supramolecular self-assembly, afforded by tetrameric R-4(4)(12) rings of C-2 symmetry in the crystal structures of 2-hydroxy-1-cyclopentanecarboxylic acid, 2-hydroxy-1-cyclohexanecarboxylic acid and 2-hydroxy-1-cycloheptanecarboxylic acid. Acta Crystallographica Section B, 58. pp. 494-501. ISSN 0108-7681

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Abstract

Determination of the crystal structures of the homologous (1R*,2R*)-trans-2-hydroxy-1-cyclopentanecarboxylic acid (5T), (1R*,2S*)-cis-2-hydroxy-1-cyclohexanecarboxylic acid (6C) and (1R*,2S*)-cis-2-hydroxy-1-cycloheptanecarboxylic acid (7C) proved a predicted pattern of supramolecular close packing. The prediction was based on the common features observed in the crystal structures of six related 2-hydroxy-1-cyclopentanecarboxylic acids and analogous carboxamides [Kalman et al. (2001). Acta Cryst. B57, 539-550]. This pattern is characterized by tetrameric R-4(4)(12) rings of C-2 symmetry formed from dimeric R-2(2)(12) rings. The C-2 symmetry of such tetramers is not common in the literature, usually they have C-i symmetry. Both types of tetramers are formed from dimers with similar or opposite orientation. The R-2(2)(12) dimers differ in their hydrogen bonds. In 5T the monomers are joined by a pair of O1-H ... O2=C bonds, whereas in 7C they are joined by a pair of O3-H...O1-H bonds. In 6C 60% of the disordered R-2(2)(12) dimers are similar to those in 7C, while 40% resemble those in 5T. Apart from these hydrogen-bonding differences and the ring-size differences, the three crystals exhibit isostructurality.

Item Type: Article
Uncontrolled Keywords: state,isostructurality
Faculty \ School: Faculty of Science > School of Pharmacy
Depositing User: Rachel Smith
Date Deposited: 19 May 2011 10:53
Last Modified: 21 Apr 2020 20:48
URI: https://ueaeprints.uea.ac.uk/id/eprint/30976
DOI: 10.1107/s0108768102001854

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