CRYSTAL STRUCTURE HIRSHFELD SURFACE AND COMPUTATIONAL ANALYSIS OF 4-CHLOROPHENYL BENZIMIDAZOLE AND 3-CHLOROPHENYL BENZOTHIAZOLE

Abstract

The crystal structures, Hirshfeld surface analysis, and computational studies of 4-chlorophenyl benzimidazole and 3-chlorophenyl benzothiazole have been presented. Compound I crystallized in the monoclinic space group I2/a whilst compound II crystallized in the orthorhombic space group Pbca. Both compounds had 8 molecules in their unit cells. The experimental and computed bond lengths and bond angles showed good agreement among the results with varying deviations from each other. Hirshfeld surface analysis of the compounds revealed that the most significant contributions to the crystal packing for compound I came from H⋯H (28.7%), H⋯C/C⋯H (26.5%), Cl⋯H (18.1%) and H⋯N/N⋯H (4.5%) whilst the atoms contributing to the crystal packing in compound II were H⋯H (34.5%), H⋯C/C⋯H (30.1%), Cl⋯H (12.5%) , H⋯N/N⋯H (10.2%), Cl⋯C (4.1%), Cl⋯N (1.9%) and Cl⋯Cl (2.1%). This work presents the first comparison of the computed and experimental bond parameters, Hirshfeld analysis and the HOMO-LUMO analysis of 4-chlorophenylbenzimidazole and 3-chlorophenylbenzothiazole, providing the basis for comparison of bulkier bioactive benzimidazole and benzothiazole derivatives.