Acta Crystallographica Section B

Structural Science

Volume 60, Part 1 (February 2004)

Acta Cryst. (2004). B60, 90-96 [doi:10.1107/S0108768103029173]

Supramolecular assembling using synthons with NH-CO(S)-CS-NH and NH-CO-CO-NH functionalities: crystal structures of (S,S)-N,N'-monothiooxalyldileucine methyl ester and its dithio analogue

B. Kojic-Prodic, B. Peric, Z. Stefanic, A. Meden, J. Makarevic, M. Jokic and M. Zinic

Abstract: To compare the structural properties of oxalamide and thiooxalamide groups in the formation of hydrogen bonds suitable for supramolecular assemblies a series of retropeptides was studied. Some of them, having oxalamide bridges, are gelators of organic solvents and water. However, retropeptides with oxygen replaced by the sp² sulfur have not exhibited such properties. The crystal structures of the two title compounds are homostructural, i.e. they have similar packing arrangements. The monothio compound crystallizes in the orthorhombic space group P2₁2₁2₁ with two molecules in the asymmetric unit arranged in a hydrogen-bond network with an approximate 4₁ axis along the crystallographic b axis. However, the dithio and dioxo analogues crystallize in the tetragonal space group P4₁ with similar packing patterns and hydrogen-bonding systems arranged in agreement with a crystallographic 4₁ axis. Thus, these two analogues are isostructural having closely related hydrogen-bonding patterns in spite of the different size and polarity of oxygen and sulfur which serve as the proton acceptors.

Online 21 January 2004


	Structure factor file (CIF format) (438.8 kbytes) Contains datablock I

	Structure factor file (CIF format) (139.9 kbytes) Contains datablock II

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