Substituent position effect on the crystal structures of N-phenyl-2-phthalimidoethanesulfonamide derivatives
Articles > Article · 2017
Authors: Resul Sevincek, Duygu Barut Celepci, Serap Koktas Koca, Özlem AKGÜL, Muittin Aygun
Acta Crystallographica Section C Structural Chemistry, Journal Indexed in SCI Expanded, International, WoS, 2017, vol 74, pp 31-36
DOI: 10.1107/s2053229617017442
Summary
In order to determine the impact of different substituents and their positions on intermolecular interactions and ultimately on the crystal packing, unsubstituted N-phenyl-2-phthalimidoethanesulfonamide, C16H14N2O4S, (I), and the N-(4-nitrophenyl)-, C16H13N3O6S, (II), N-(4-methoxyphenyl)-, C16H16N3O6S, (III), and N-(2-ethylphenyl)-, as the monohydrate, C18H18N2O4S·H2O, (IV), derivatives have been characterized by single-crystal X-ray crystallography. Sulfonamides (I) and (II) have triclinic crystal systems, while (III) and (IV) are monoclinic. Although the molecules differ from each other only with respect to small substituents and their positions, they crystallized in different space groups as a result of differing intra- and intermolecular hydrogen-bond interactions. The structures of (I), (II) and (III) are stabilized by intermolecular N—H...O and C—H...O hydrogen bonds, while that of (IV) is stabilized by intermolecular O—H...O and C—H...O hydrogen bonds. All four structures are of interest with respect to their biological activities and have been studied as part of a program to develop anticonvulsant drugs for the treatment of epilepsy.