Crystal Structures of Isomeric N-(2-chlorophenyl)-2,5-dimethoxybenzene-sulfonamide and N-(4-chlorophenyl)-2,5-dimethoxybenzenesulfonamide

Shakuntala K; Naveen S; Lokanath NK; Suchetan PA

Abstract

Crystal Structures of Isomeric N-(2-chlorophenyl)-2,5-dimethoxybenzene-sulfonamide and N-(4-chlorophenyl)-2,5-dimethoxybenzenesulfonamide

Author(s): Shakuntala K, Naveen S, Lokanath NK, Suchetan PA

Crystal structures of two isomeric compounds of formula C14H14NO4SCl, namely N-(2-chlorophenyl)-2,5-dimethoxybenzenesulfonamide (I) and N-(4-chlorophenyl)-2,5-dimethoxy-benzenesulfonamide (II) are described. Both the compounds crystallize in the triclinic crystal system and P-1 space group with the asymmetric unit of (I) consisting of one molecule, while, that of (II) containing two (Molecules A and B). The molecule of (I) is U shaped with the central –Carm-S-N-Carm- segment making a torsional angle of 75.5o, while, the two symmetry independent molecules of (II) are V shaped with the central segments making torsions of -57.8(9)o in Mol. A and -59.6(10)o in Mol. B. The dihedral angle between the benzene rings is 84.73(7)o in (I), and, 82.72(3) and 80.80(3)o respectively in molecules A and B of (II). The supramolecular architecture exhibited by both is built by the common intermolecular interactions: N-H…O hydrogen bonds, C-H...O, C-H...πaryl and πaryl... πaryl interactions. However, the role played by these interactions in supramolecular aggregation of molecules of (I) and (II) are different to some extent, and as a result, (I) consists of 2 dimensional (2D) sheets, while, (II) forms 1D zig-zag chains.

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