Acta Crystallographica Section E

Volume 67, Part 8 (August 2011)

organic compounds

 

(1S*,3S*,8S*,10S*)-10-Fluoro-15-oxatetracyclo[6.6.1.0^1,10.0^3,8]pentadeca-5,12-dien-3-ol

G. Mehta and S. Sen

Abstract: The title compound, C₁₄H₁₇FO₂, was obtained from anti-4a,9a:8a,10a-diepoxy-1,4,4a,5,8,8a,9,9a,10,10a-decahydroanthracene via tandem hydrogen-fluoride-mediated epoxide ring-opening and transannular oxacyclization. With the two cyclohexene rings folded towards the oxygen bridge, the title tetracyclic fluoroalcohol molecule displays a conformation reminiscent of a pagoda. The crystal packing is effected via intermolecular O-HO hydrogen bonds, which link the molecules into a zigzag chain along the b axis.

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