Abstract
The title compound, C15H24O2 [systematic name: (4S,4aR,6R,8aR)-4a-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)octahydronaphthalen-1(2H)-one], features two edge-shared six-membered rings with the hydroxyl and methyl substituents at this bridge being trans. One adopts a flattened chair conformation with the C atoms bearing the carbonyl and methyl substituents lying 0.5227 (16) and 0.6621 (15) Å, respectively, above and below the mean plane through the remaining four C atoms (r.m.s. deviation = 0.0145 Å). The second ring, bearing the prop-1-en-2-yl group, has a chair conformation. Supramolecular helical chains along the b axis are found in the crystal packing, which are sustained by hydroxy–carbonyl O—H⋯O hydrogen bonding.
Highlights
The title compound, C15H24O2 [systematic name: (4S,4aR,6R,8aR)-4a-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)octahydronaphthalen-1(2H)-one], features two edge-shared sixmembered rings with the hydroxyl and methyl substituents at this bridge being trans
Supramolecular helical chains along the b axis are found in the crystal packing, which are sustained by hydroxy–carbonyl O—HÁ Á ÁO hydrogen bonding
R[F 2 > 2(F 2)] = 0.030 wR(F 2) = 0.083 S = 1.03 2631 reflections 161 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement
Summary
Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.002 A; R factor = 0.030; wR factor = 0.083; data-to-parameter ratio = 16.3. The title compound, C15H24O2 [systematic name: (4S,4aR,6R,8aR)-4a-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)octahydronaphthalen-1(2H)-one], features two edge-shared sixmembered rings with the hydroxyl and methyl substituents at this bridge being trans. One adopts a flattened chair conformation with the C atoms bearing the carbonyl and methyl substituents lying 0.5227 (16) and 0.6621 (15) A , respectively, above and below the mean plane through the remaining four C atoms (r.m.s. deviation = 0.0145 A ). The second ring, bearing the prop-1-en-2-yl group, has a chair conformation. Related literature For the first isolation and the spectroscopic data of corymbolone, see: Garbarino et al (1985). For the synthesis of corymbolone in racemic form, see: Ferraz et al (2006)
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