3',3',4',4'-TETRAFLUORO-4-IODO-1-PHENYL-2,3-CYCLOBUTENONAPHTHALENE

C18H9F4I, M(r) = 428.2, orthorhombic, Pbca, a = 20.039 (7), b = 18.800 (9), c = 8.167 (3) angstrom, V = 3077 angstrom 3, Z = 8, D(x) 1.848 Mg m-3, F(000) = 1648, lambda(Mo K-alpha) = 0.71069 angstrom, mu = 2.09 mm-1, T = 293 K, R = 0.034 for 1555 unique reflexions [F greater-than-or-equal-to 3-sigma(F)]. The title compound is a by-product (up to 11.5%) in the synthesis of 3,3-difluoro-3-iodo-1-phenylpropyne, Ph-C = C-CF2I. It would have been formed by dimerization of the latter via elimination of iodine to give 1,6-diphenyltetrafluorohexa-1,5-diyne, Ph-C = C-CF2-CF2C = C-Ph, followed by a double cyclization, induced by electrophilic attack by iodine on a carbon adjacent to a phenyl ring. The planar naphthalene moiety retains a bond shortening pattern typical of its class and is inclined at 54 (1)-degrees to the phenyl ring. This ring is directed away from a C-I bond, which at 2.094 (6) angstrom falls within the expected range.