title: 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.
authors: Department of Physics, Faculty of Sciences, Dokuz Eylül University, Buca İzmir, Turkey.
authors: Serap Köktaş
authors: SK
authors: Koca
authors: Department of Physics, Faculty of Sciences, Dokuz Eylül University, Buca İzmir, Turkey.
authors: Resul
authors: R
authors: Sevinçek
authors: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University, Bornova İzmir, Turkey.
authors: Özlem
authors: Ö
authors: Akgül
authors: Department of Physics, Faculty of Sciences, Dokuz Eylül University, Buca İzmir, Turkey.
authors: Muhittin
authors: M
authors: Aygün
mesh_terms: D002713:Chlorine / Q000737:chemistry*; D003460:Crystallization; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007536:Isomerism; D015394:Molecular Structure; D010797:Phthalimides / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: C000603573:N-(2-chlorophenyl)-2-phthalimidoethanesulfonamide; C000603574:N-(3-chlorophenyl)-2-phthalimidoethanesulfonamide; C000603572:N-(4-chlorophenyl)-2-phthalimidoethanesulfonamide; D010797:Phthalimides; D013449:Sulfonamides; D002713:Chlorine
keywords: Newman projection; anticonvulsant drugs; crystal structure; epilepsy; ethanesulfonamide; pharmaceuticals; positional isomerization