Acta Crystallographica Section B

Structural Science

Volume 58, Part 3 Number 2 (June 2002)

Acta Cryst. (2002). B58, 494-501    [doi:10.1107/S0108768102001854]

Novel, predicted patterns of supramolecular self-assembly, afforded by tetrameric rings of C₂ symmetry in the crystal structures of 2-hydroxy-1-cyclopentanecarboxylic acid, 2-hydroxy-1-cyclohexanecarboxylic acid and 2-hydroxy-1-cycloheptanecarboxylic acid

A. Kálmán, L. Fábián, G. Argay, G. Bernáth and Z. Gyarmati

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 [Kálmán et al. (2001). Acta Cryst. B57, 539-550]. This pattern is characterized by tetrameric rings of C₂ symmetry formed from dimeric rings. The C₂ 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 dimers differ in their hydrogen bonds. In 5T the monomers are joined by a pair of O1-HO2=C bonds, whereas in 7C they are joined by a pair of O3-HO1-H bonds. In 6C 60% of the disordered 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.

Online 29 May 2002

	Structure factor file (CIF format) (77.8 kbytes) Contains datablock 5ts
	Structure factor file (CIF format) (78.8 kbytes) Contains datablock 6cs
	Structure factor file (CIF format) (84.8 kbytes) Contains datablock 7cs

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