Positional isomeric effect on the crystallization of chlorine-substituted N-phenyl-2-phthalimidoethanesulfonamide derivatives

Abstract

The ortho-, para- and meta-chloro-substituted N-chlorophenyl-2-phthalimidoethanesulfonamide derivatives, C16H13ClN2O4S, have been structurally characterized by single-crystal X-ray crystallography. N-(2-Chlorophenyl)-2-phthalimidoethanesulfonamide, (I), has orthorhombic (P2(1)2(1)2(1)) symmetry, N-(4-chlorophenyl)-2-phthalimidoethanesulfonamide, (II), has triclinic (P1¯) symmetry and N-(3-chlorophenyl)-2-phthalimidoethanesulfonamide, (III), has monoclinic (P2(1)/c) symmetry. The molecules of (I)-(III) are regioisomers which have crystallized in different space groups as a result of the differing intra- and intermolecular hydrogen-bond interactions which are present in each structure. Compounds (I) and (II) are stabilized by N-H···O and C-H···O hydrogen bonds, while (III) is stabilized by N-H···O, C-H···O and C-H···Cl hydrogen-bond interactions. The structure of (II) also displays π-π stacking interactions between the isoindole and benzene rings. All three structures are of interest with respect to their biological activities and have been studied as part of a programme to develop anticonvulsant drugs for the treatment of epilepsy.

Keywords: Newman projection; anticonvulsant drugs; crystal structure; epilepsy; ethanesulfonamide; pharmaceuticals; positional isomerization.