The face-to-face stacking interaction between phenyl and perfluorophenyl groups is emerging as a common noncovalent interaction. To explore the generality of this supramolecular synthon, the solid-state packing structure and reactivity of several monoolefins and diolefins substituted with phenyl and perfluorophenyl groups was investigated. Of the seven crystalline or cocrystalline materials investigated, six were found to undergo a photochemically induced [2+2] reaction in the solid state. By determining the stereochemistry of the photoproduct and/or X-ray structural analysis of the olefinic precursors, the stacked interaction between phenyl and perfluorophenyl groups in the photoactive crystals were revealed.

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Crystal Size: 0.10 x 0.11 x 0.23 mm pcj. = 2.57 g cm Crystal System: Orthorhombic Space group: Cm a = 17.669(5) A b = 9.081(2) A c = 6.804(2) A V = 1091.7(5) A 3 Z=4 Lattice parameters: 29 reflections 9.50 <0 < 10.50 p. = 134.5 cm-1 Tansmission co Variable-temperature P! diffractometer 0-20 scan MoKa, A = 0.7107A Graphite mono 20 range: 20-600-24 < h < 21,-T = 294K Number of reflections measured: 6993 Number of idei Number with FO > 0: 868 Number with F. Standard reflections: 3 every 97 data Variation: within GOFmerge: 1.06 for 877 multiples Rmerge: 0.018 fo