Acta Crystallographica Section E

Structure Reports Online

Volume 63, Part 10 (October 2007)

organic compounds

Acta Cryst. (2007). E63, o4094 [ doi:10.1107/S1600536807044704 ]

Unexpected crystallization of 1,3-bis(4-fluorophenyl)propan-2-one in paratone oil

I. A. Guzei, K. J. Kolonko and H. J. Reich

Abstract: The title compound, C₁₅H₁₂F₂O, crystallizes in paratone oil as a room-temperature decomposition product of the crystalline air- and moisture-sensitive lithium enolate of 1,3-di(p-fluorophenyl)acetone diethyl ether solvate. Such spontaneous crystallization in paratone oil is rare, yet in this case it yielded X-ray quality crystals. The title compound can be prepared directly by a modified procedure of Resendiz & Garibay [Org. Lett. (2005), 7, 371-374]. The molecular features are typical: the endocyclic angles at the electron-withdrawing F substituent average 123.0 (2)°, while the endocyclic angles at the methylene C atom average 118.3 (3)°. These findings are in excellent agreement with the values of 122.3 and 118.5° computed for the theoretically (DFT, density functional theory) optimized geometry of the title compound.