Acta Crystallographica Section C

Crystal Structure Communications

Volume 61, Part 4 (April 2005)

organic compounds

sk1816 scheme

Acta Cryst. (2005). C61, o221-o226 [doi:10.1107/S0108270105004701]

Trifluoromethyl derivatives of pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane

A. Linden, J. Romanski, G. Mloston and H. Heimgartner

Abstract: Three cage-like polycyclic compounds, viz. exo-8-(trifluoromethyl)pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecan-endo-8-ol, C₁₂H₁₃F₃O, 5-(trifluoromethyl)-4-oxahexacyclo[5.4.1.0^2,6.0^3,10.0^5,9.0^8,11]dodecan-3-ol, C₁₂H₁₁F₃O₂, and N-[exo-11-(trifluoromethyl)-endo-11-(trimethylsilyloxy)pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecan-8-ylidene]aniline methanol solvate, C₂₁H₂₄F₃NOSi·CH₄O, were obtained from the corresponding oxo derivatives by nucleophilic trifluoromethylation with (trifluoromethyl)trimethylsilane in 1,2-dimethoxyethane solution in the presence of CsF. The crystal structures show that the addition of trifluoromethanide occurs exclusively from the exo face of the polycyclic ketones. Further examination of the crystal structures, together with that of the starting pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-8,11-dione, C₁₁H₁₀O₂, showed that increasing substitution at the 8- and/or 11-positions in the cage molecules increases the non-bonded intramolecular CC distances at the mouth of the cage and changes the puckering of the five-membered rings involving the 8- and 11-positions from an envelope towards a distorted half-chair conformation. Intermolecular co-operative O-HO hydrogen bonds in the endo-8-ol compound link the molecules into tetramers.

Formula: C₁₂H₁₃F₃O, C₁₁H₁₀O₂, C₁₂H₁₁F₃O₂ and C₂₁H₂₄F₃NOSi·CH₄O


	Structure factor file (CIF format) (62.7 kbytes) Contains datablock II

	Structure factor file (CIF format) (173.9 kbytes) Contains datablock III

	Structure factor file (CIF format) (111.8 kbytes) Contains datablock V

	Structure factor file (CIF format) (294.8 kbytes) Contains datablock VII

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