Non-covalent Interactions in Dihalogenated Compounds Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I). Synthesis, Crystal Structure, and Hirshfeld Surface

In this work, the synthesis and structural study by means of single -crystal X-ray diffraction of compounds of general formula Ch(C6H4CH2X)2 (Ch = O, S; X = Cl, Br, I) is reported. These compounds contain two flexible hydrocarbonated arms -CH2-X in the ortho positions to the Ch heteroatom. These compounds were synthesized through a linear synthesis starting from diphenylether or diphenylsulfide. Based on the structural analysis, we describe the more relevant molecular features as well as the non -covalent interactions that the heavy halogen atoms display with other moieties that promote the cohesion of the crystal arrangement. The Hirshfeld analysis displayed that the X center dot center dot center dot pi, X center dot center dot center dot X, and C-H center dot center dot center dot X interactions are quite significant in the crystal arrangement.