Hydrogen bonding between the sulfur oxygens and the acidic alpha-hydrogens in sulfoxides and sulfones is proposed as a supramol. synthon in crystal engineering. A systematic anal. of supramol. interactions in the solid state of a series of structurally related aryl benzyl sulfides, sulfoxides and sulfones was undertaken to establish the extent to which such hydrogen bonds persist as a structure detg. feature in the solid state. The impact of the level of oxidn. at sulfur, steric and electronic effects of substituents on the aryl rings and Me substitution alpha to the sulfur functional group on the solid state structure of the compds. have been explored. The impact of stereochem. features, including relative and abs. stereochem., is also discussed.