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Positional isomeric effect on the crystallization of chlorine‐substituted N ‐phenyl‐2‐phthalimidoethanesulfonamide derivatives
Author(s) -
Köktaş Koca Serap,
Sevinçek Resul,
Akgül Özlem,
Aygün Muhittin
Publication year - 2015
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229615015223
Subject(s) - triclinic crystal system , monoclinic crystal system , hydrogen bond , crystallography , chemistry , stacking , orthorhombic crystal system , crystal structure , molecule , benzene , stereochemistry , organic chemistry
The ortho ‐, para ‐ and meta ‐chloro‐substituted N ‐chlorophenyl‐2‐phthalimidoethanesulfonamide derivatives, C 16 H 13 ClN 2 O 4 S, have been structurally characterized by single‐crystal X‐ray crystallography. N ‐(2‐Chlorophenyl)‐2‐phthalimidoethanesulfonamide, (I), has orthorhombic ( P 2 1 2 1 2 1 ) symmetry, N ‐(4‐chlorophenyl)‐2‐phthalimidoethanesulfonamide, (II), has triclinic ( P ) symmetry and N ‐(3‐chlorophenyl)‐2‐phthalimidoethanesulfonamide, (III), has monoclinic ( P 2 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.