Substituent position effect on the crystal structures of N-phenyl-2-phthalimidoethanesulfonamide derivatives.

In order to determine the impact of different substituents and their positions on intermolecular interactions and ultimately on the crystal packing, unsubstituted N-phenyl-2-phthalimidoethanesulfonamide, C16 H14 N2 O4 S, (I), and the N-(4-nitrophenyl)-, C16 H13 N3 O6 S, (II), N-(4-methoxyphenyl)-, C16 H16 N3 O6 S, (III), and N-(2-ethylphenyl)-, as the monohydrate, C18 H18 N2 O4 S·H2 O, (IV), derivatives have been characterized by single-crystal X-ray crystallography. Sulfonamides (I) and (II) have triclinic crystal systems, while (III) and (IV) are monoclinic. Although the molecules differ from each other only with respect to small substituents and their positions, they crystallized in different space groups as a result of differing intra- and intermolecular hydrogen-bond interactions. The structures of (I), (II) and (III) are stabilized by intermolecular N-H...O and C-H...O hydrogen bonds, while that of (IV) is stabilized by intermolecular O-H...O and C-H...O hydrogen bonds. All four structures are of interest with respect to their biological activities and have been studied as part of a program to develop anticonvulsant drugs for the treatment of epilepsy.