Tapes, Sheets, and Prisms. Identification of the Weak C−F Interactions that Steer Fullerene−Porphyrin Cocrystallization

Tetra(pentafluorophenyl)porphyrin (H2TPFPP) has been cocrystallized with C60 from arene solvents to give H2TPFPP·C60, 1, H2TPFPP·C60·8Benzene, 3, and 3H2TPFPP·2C60·6Toluene, 4. Their X-ray structures have been determined to identify the supramolecular interactions that lead to tape, sheet, and prismatic packing motifs. In addition to close fullerene−porphyrin π−π interactions, attractive C−F···H−C interactions are important in connecting the C6F5 groups of one porphyrin to the pyrrole positions of a neighbor. This interaction is also seen in the structure of the free-base porphyrin H2TPFPP·3p-Xylene, 2.