Positional isomeric effect on the crystallization of chlorine-substituted N-phenyl-2-phthalimidoethanesulfonamide derivatives
Küçük Resim Yok
Tarih
2015
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
International Union of Crystallography
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
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 ?-? 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. © 2015 International Union of Crystallography.
Açıklama
Anahtar Kelimeler
anticonvulsant drugs, crystal structure, epilepsy, ethanesulfonamide, Newman projection, pharmaceuticals, positional isomerization
Kaynak
Acta Crystallographica Section C: Structural Chemistry
WoS Q Değeri
Scopus Q Değeri
Q3
Cilt
71
