Supramolecular synthons in fluorinated benzyl nitrophenyl sulfides

Two crystalline benzyl phenyl sulfides, bearing at the same time both a pentafluorophenyl and a nitrophenyl moiety in two different assemblies, were investigated by means of single crystal X-ray diffraction. The main assembly interactions were recognized and compared with the different behaviors of analogous sulfides bearing only one of these two functional groups. Since short contacts involving fluorine atoms have been a source of controversy, their contribution to the stability of the crystal was analyzed both with the help of Hirshfeld surface analysis, and with a comparison with items in the Cambridge Structural Database. The situation of a gauche-conformed sulfide having two contemporary interactions involving electron poor aryl groups is of particular interest