Acta Crystallographica Section C

Crystal Structure Communications

Volume 59, Part 5 (May 2003)

Acta Cryst. (2003). C59, o254-o256 [doi:10.1107/S010827010300684X]

The sesquiterpenoid nootkatone and the absolute configuration of a dibromo derivative

A. M. Sauer, F. R. Fronczek, B. C. R. Zhu, W. E. Crowe, G. Henderson and R. A. Laine

Abstract: Nootkatone, or (4R,4aS,6R)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)naphthalen-2(3H)-one, C₁₅H₂₂O, a sesquiterpene with strong repellent properties against Formosan subterranean termites and other insects, has the valencene skeleton. The dibromo derivative (1S,3R,4S,4aS,6R,8aR)-1,3-dibromo-6-isopropyl-4,4a-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-one, C₁₅H₂₄Br₂O, has two independent molecules in the asymmetric unit, which differ in the rotation of the isopropyl group with respect to the main skeleton. The C-Br distances are in the range 1.950 (4)-1.960 (4) Å. Both independent molecules form zigzag chains, with very short intermolecular carbonyl-carbonyl interactions, having the perpendicular motif and OC distances of 2.886 (6) and 2.898 (6) Å. These chains are flanked by intermolecular BrBr interactions of distances in the range 4.067 (1)-4.218 (1) Å. The absolute configuration of the dibromo derivative was determined, from which that of nootkatone was inferred.

Formula: C₁₅H₂₂O and C₁₅H₂₄Br₂O

Online 18 April 2003


	Structure factor file (CIF format) (76.1 kbytes) Contains datablock I

	Structure factor file (CIF format) (459.1 kbytes) Contains datablock II

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