Principles of crystal packing in O-isopropyl-N-aryl-thiocarbamides: iPrOC(S)N(H)C6H4-4-Y: Y = H, Cl, and Me

Abstract

Crystallographic analysis shows no significant influence is exerted by the nature of Y upon the molecular parameters of the central O–C(S)–N(H) chromophore in the structures of iPrOC(S)N(H)C6H4-4-Y, for Y = H (1), Cl (2), and Me (3); this is verified by a theoretical study. The crystal structures each feature dimeric aggregates as a result of the uniform formation of the {⋯H–N–CS}2, thioamide, synthon. An analysis of the crystal structures shows that the substitution of the chloride atom in (2) by a methyl group, leading to (3), has a profound influence on the crystal packing owing to the participation of the chloride atom in structure directing C–H⋯Cl interactions that link the dimeric aggregates into a double layer structure. In the structures of (1) and (3), C–H⋯S interactions serve to connect molecules into columnar and layer structures, respectively, with weak C–H⋯O (and π⋯π interactions in (3)) further reinforcing the crystal packing.