Structure and Conformation of Solvated 1-(4-methoxybenzenesulfonyl)-5-oxo-pyrrolidine-2-carboxamide

Abstract

The crystal structure and molecular conformation of solvated 1-(4-methoxybenzenesulfonyl)-5-oxo-pyrrolidine-2-carboxamide (C12H14O5N2S.H2O), synthesized and biologically evaluated as a possible antineoplastic agent, have been studied by X-ray analysis and AM1 molecular orbital methods. The compound crystallizes in the monoclinic space group P21, with a = 9.661(4), b = 7.246(3), c = 11.378(5)Å, β = 113.42(2)°, Z = 2. The structure has been solved by direct methods and refined to R = 0.0438 for 1721 observed reflections. The crystal structure consists of an essentially planar methoxyphenyl ring linked to a 2-carboxamide substituted oxo-pyrrolidine moiety via sulfonyl group and a lattice water molecule. The conformational analysis of the title compound investigated by semi-empirical quantum mechanical AM1 calculations shows a good agreement with the X-ray structure except a rotation of the carboxamide moiety about the C (oxo-pyrrolidine) - C (carboxamide) bond. In the solid state, the molecules translated in the b-direction are linked by intermolecular N-H···O hydrogen bonds to form infinite one-dimensional chain.