Acta Cryst. (2005). E61, o2120-o2122  [ doi:10.1107/S1600536805018258 ]

2-(Acetylamino)-N-benzyl-2-(ethylsulfinyl)acetamide: structural basis for lack of anticonvulsant activity

A. Hempel, N. Camerman, A. Camerman and D. Mastropaolo

Abstract: In the crystal structure of the title compound, C₁₃H₁₈N₂O₃S, there are two independent molecules in the asymmetric unit. Both molecules have linearly extended conformations, with interplanar angles between the two amide groups of 150.4 (3) and 148.8 (3)°. In addition to the standard N-HO hydrogen bonds, which form infinite molecular chains parallel to the a axis, a host of weak non-standard C-HO bonds and van der Waals contacts contribute to the crystal packing. Although the molecule contains stereochemical features consonant with anticonvulsant properties, steric interference by the ethylsulfinyl group may prevent interactions with receptors.

Online 17 June 2005

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