Crystal Research and Technology
Cryst. Res. Technol. 37 (2002) 309 - Abstract -

S. Banerjee, A. K. Mukherjee , D. Goswami*, A. U. De* , M. Helliwell**

Department of Physics, Jadavpur University, Calcutta, India
*Division of Medicinal & Pharmaceutical Chemistry, Department of Pharmaceutical Technology, Jadavpur University, Calcutta, India
**Department of Chemistry, University of Manchester, England

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

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.

Keywords: X-ray crystal structure, conformation, AM1 molecular mechanics, oxo-pyrrolidine derivative


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