Self-assemblies of chiral p-haloarylsulfoxides through C-H O short contacts and halogens involving interactions

Single crystal X-ray structure determination of four crystals of alkyl or aryl p-haloaryl sulfoxides is reported. Intramolecular short contacts between the ortho-hydrogen of the aryl ring and the oxygen of the sulfinyl group were found to determine the conformations of the sulfoxides. On the other hand, in the absence of classical hydrogen bond donors, crystal packing arrangements are the results of intermolecular aryl hydrogen-oxygen short contacts and of interactions involving halogen atoms. From a comparison of the structures of the investigated sulfoxides with other literature data, the crystal packings of these types of compound appear to derive from a complex balance among different interactions.