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 H 2TPFPP·C60, 1, H2TPFPP·C 60·8Benzene, 3, and 3H2TPFPP·2C 60·6Toluene, 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. © 2006 American Chemical Society.