Supramolecular architectures in N-(4-bromobenzoyl)-arylsulfonamides: crystal structures and Hirshfeld surface analysis.

Naveen, Shivalingegowda; Sudha, Achar Gurumurthy; Suresha, Erachikkaiah; Lokanath, Neratur Krishnappagowda; Suchetan, Parameshwar Adimule

A detailed analysis of the molecular packing of five N-(4-bromobenzoyl)-substituted benzenesulfonamides, i-X ~ 4-Br (1-5) [i-X = H, 2-CH3, 4-CH3, 2-Cl, 4-Cl] is presented. The intermolecular interactions and the packing patterns are evaluated along with an analysis of their Hirshfeld surfaces and fingerprint plots (FP). The crystals feature molecular self-assembly through N-H· · ·O hydrogen-bonds forming three types of supramolecular synthon: C¹1 (4) chain, R44 (16) tetramer and R²2 (8) ring. These molecular assemblies extend to form one-dimensional (1D), 2D or 3D supramolecular architectures via diverse intermolecular interactions. A study of 33 i-X ~ 4-Y (Y = H, CH3, OCH3, NO2, F, Cl, Br) structures shows the substituent on the sulfonamide ring modulates the intermolecular interactions and the subsequent supramolecular architectures drastically, with the fluoro- and bromo-substituted analogues providing distinctive self-assemblies. The R44 (16) synthon produced by N-H· · ·O hydrogen-bonds in the 4-CH3 ~ 4-Br derivative is a rare phenomenon amongst a set of 74 i-X ~ j-Y structures.

BENZENESULFONAMIDES; SUPRAMOLECULAR chemistry; CRYSTAL structure; MOLECULAR interactions; MOLECULAR self-assembly

Zeitschrift für Kristallographie. Crystalline Materials, 2017, Vol 232, Issue 11, p767

2194-4946

Academic Journal

10.1515/zkri-2016-2008