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首页> 外文期刊>Acta crystallographica. Section C, Structural chemistry. >Positional isomeric effect on the crystallization of chlorine-substituted N-phenyl-2-phthalimidoethanesulfonamide derivatives
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Positional isomeric effect on the crystallization of chlorine-substituted N-phenyl-2-phthalimidoethanesulfonamide derivatives

机译：位置异构体对氯取代的N-苯基-2-邻苯二甲酰亚胺基乙磺酰胺衍生物结晶的影响

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摘要

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 (P212121) symmetry, N-(4-chlorophenyl)-2-phthalimidoethanesulfonamide, (II), has triclinic (P) symmetry and N-(3-chlorophenyl)-2-phthalimidoethanesulfonamide, (III), has monoclinic (P21/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.
机译：已通过单晶X射线晶体学表征了邻，对氯和间氯取代的N-氯苯基-2-邻苯二甲酰亚胺乙烷磺酰胺衍生物C16H13ClN2O4S。 N-（2-氯苯基）-2-邻苯二甲酰亚胺乙磺酰胺（I）具有斜方（P212121）对称性，N-（4-氯苯基）-2-邻苯二甲酰亚胺乙磺酰胺（II）具有三斜晶（P）对称性和N-（3 -（氯苯基）-2-邻苯二甲酰亚胺乙磺酰胺（III）具有单斜（P21 / c）对称性。 （I）-（III）的分子是区域异构体，由于每个结构中存在的分子内和分子间氢键相互作用不同，它们已在不同的空间组中结晶。化合物（I）和（II）通过NH.O和CHH.O氢键稳定，而化合物（III）通过NH.O，CHH.O稳定。 O和CHH ... Cl氢键相互作用。 （II）的结构还显示了异吲哚和苯环之间的π–π堆积相互作用。这三种结构都具有生物学活性，并且已作为开发抗癫痫药治疗癫痫的计划的一部分进行了研究。

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