Does intermolecular S&z.dbd;O H-C-S&z.dbd;O hydrogen bonding in sulfoxides and sulfones provide a robust supramolecular synthon in the solid state?Electronic supplementary information (ESI) available: Tables summarising the crystallographic data and the experimental section. CCDC reference numbers 759274-759295. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c000371a

Hydrogen bonding between the sulfur oxygens and the acidic α-hydrogens in sulfoxides and sulfones is proposed as a supramolecular synthon in crystal engineering. A systematic analysis of supramolecular 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 determining feature in the solid state. The impact of the level of oxidation at sulfur, steric and electronic effects of substituents on the aryl rings and methyl substitution α to the sulfur functional group on the solid state structure of the compounds have been explored. The impact of stereochemical features, including relative and absolute stereochemistry, is also discussed. Hydrogen bonding between the sulfur oxygens and the acidic α-hydrogens in sulfoxides and sulfones has been examined as a supramolecular synthon in crystal engineering.