Crystal structure of (1S,3R,8R,9R)-2,2-di­chloro-3,7,7-tri­methyl-10-methylenetri­cyclo­[6.4.0.01,3]dodecan-9-ol

The title compound, C16H24Cl2O, was synthesized by treating (1S,3R,8S,9R,10S)-2,2-di­chloro-3,7,7,10-tetra­methyl-9,10-ep­oxy­tri­cyclo­[6.4.0.01,3]dodecane with a concentrated solution of hydro­bromic acid. It is built up from three fused rings: a cyclo­heptane ring, a cyclo­hexyl ring bearing alkene and hy­droxy substituents, and a cyclo­propane ring bearing two chlorine atoms. The asymmetric unit contains two mol­ecules linked by an O—H⋯O hydrogen bond. In the crystal, further O—H⋯O hydrogen bonds build up an R44(8) cyclic tetra­mer. One of the mol­ecules presents disorder that affects the seven-membered ring. In both mol­ecules, the six-membered rings display a chair conformation, whereas the seven-membered rings display conformations inter­mediate between boat and twist-boat for the non-disordered mol­ecule and either a chair or boat and twist-boat for the disordered mol­ecule owing to the disorder. The absolute configuration for both mol­ecules is 1S,3R,8R,9R and was deduced from the chemical pathway and further confirmed by the X-ray structural analysis.