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(4R,4aS,4bS,7R,10aR)-4-Hy-droxy-4a,7-dimethyl-2-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-deca-hydro-phenanthren-1-one.

ABSTRACT: In the title compound, C(19)H(28)O(2), the A ring adopts a chair conformation, and each of the B and C rings adopts a distorted half-chair conformation with the methine C atom in the CH(2)C(H)C(=O) residue, common to both rings, lying 0.6397?(19) and 0.6328?(18)?Å out of the approximate plane defined by the remaining five C atoms (r.m.s. deviations = 0.0791 and 0.0901?Å for rings B and C, respectively). Helical supra-molecular chains along the a axis mediated by hy-droxy-carbonyl O-H?O hydrogen bonds feature in the crystal packing.

SUBMITTER: Caracelli I

PROVIDER: S-EPMC3247520 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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(4R,4aS,4bS,7R,10aR)-4-Hy-droxy-4a,7-dimethyl-2-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-deca-hydro-phenanthren-1-one.

Caracelli Ignez I Zukerman-Schpector Julio J Machado André T Lousada AT Brocksom Timothy J TJ Ferreira M Lúcia ML Tiekink Edward R T ER

Acta crystallographica. Section E, Structure reports online 20111029 Pt 11

In the title compound, C(19)H(28)O(2), the A ring adopts a chair conformation, and each of the B and C rings adopts a distorted half-chair conformation with the methine C atom in the CH(2)C(H)C(=O) residue, common to both rings, lying 0.6397 (19) and 0.6328 (18) Å out of the approximate plane defined by the remaining five C atoms (r.m.s. deviations = 0.0791 and 0.0901 Å for rings B and C, respectively). Helical supra-molecular chains along the a axis mediated by hy-droxy-carbonyl O-H⋯O hydrogen ...[more]

PMID: 22220138

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(4R*,4aS*,4bS*,5R*,10aR*)-4-Hy-droxy-4a,5-dimethyl-2-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-deca-hydro-phenan-thren-1-one.

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Project description:The crystal structure of the title compound, C(16)H(28)O, features C-H?O hydrogen bonds making C(6) zigzag chains along one 2(1) screw axis. Within the limits of the data collection affected by crystal quality, the Hooft parameter gave correct indications of the known molecular chirality based on the single O atom anomalous dispersion in contrast to the indeterminate Flack value. Synthetic steps starting from manool are reported.

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(E)-(4-Chloro-benzyl-idene){[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa-hydro-1-phenanthryl]-methyl}amine.

Project description:The title compound, C(27)H(34)ClN, has been synthesized from 4-chloro-benzaldehyde and dehydro-abietylamine. There are two unique mol-ecules in the unit cell. Each mol-ecule has three chiral centres, which exhibit R, S and R absolute configurations. The two cyclo-hexane rings form a trans ring junction with classical chair and half-chair conformations.

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