Koca Serap Köktaş, Sevinçek Resul, Akgül Özlem, Aygün Muhittin
Department of Physics, Faculty of Sciences, Dokuz Eylül University, Buca İzmir, Turkey.
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University, Bornova İzmir, Turkey.
Acta Crystallogr C Struct Chem. 2015 Sep;71(Pt 9):839-43. doi: 10.1107/S2053229615015223. Epub 2015 Aug 27.
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.
邻氯、对氯和间氯取代的N-氯苯基-2-邻苯二甲酰亚胺基乙磺酰胺衍生物（C16H13ClN2O4S）已通过单晶X射线晶体学对其结构进行了表征。N-(2-氯苯基)-2-邻苯二甲酰亚胺基乙磺酰胺（I）具有正交晶系（P2(1)2(1)2(1)）对称性，N-(4-氯苯基)-2-邻苯二甲酰亚胺基乙磺酰胺（II）具有三斜晶系（P1¯）对称性，N-(3-氯苯基)-2-邻苯二甲酰亚胺基乙磺酰胺（III）具有单斜晶系（P2(1)/c）对称性。（I）-（III）的分子是区域异构体，由于每种结构中存在不同的分子内和分子间氢键相互作用，它们以不同的空间群结晶。化合物（I）和（II）通过N-H···O和C-H···O氢键稳定，而（III）通过N-H···O、C-H···O和C-H···Cl氢键相互作用稳定。（II）的结构还显示异吲哚环和苯环之间存在π-π堆积相互作用。所有这三种结构因其生物活性而备受关注，并作为开发用于治疗癫痫的抗惊厥药物计划的一部分进行了研究。
