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(1S,3R,8R,11S)-2,2-Dichloro-3,7,7,10-tetra-methyl-tricyclo-[6.4.0.0]dodec-9-en-11-ol.

ABSTRACT: The title compound, C(16)H(24)Cl(2)O, was synthesized from ?-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from essential oil of the Atlas cedar (Cedrus atlantica). The two fused rings exhibit different conformations: the six-membered ring has a screw-boat conformation, while the seven-membered ring displays a boat conformation. The dihedral angle between the two rings is 56.56?(18)°. In the crystal, mol-ecules aggregate into supra-molecular chains along the c axis mediated by O-H?O hydrogen bonds.

SUBMITTER: Benharref A

PROVIDER: S-EPMC3052100 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature

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(1S,3R,8R,11S)-2,2-Dichloro-3,7,7,10-tetra-methyl-tricyclo-[6.4.0.0]dodec-9-en-11-ol.

Benharref Ahmed A Lassaba Essêdiya E Avignant Daniel D Oudahmane Abdelghani A Berraho Moha M

Acta crystallographica. Section E, Structure reports online 20110212 Pt 3

The title compound, C(16)H(24)Cl(2)O, was synthesized from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from essential oil of the Atlas cedar (Cedrus atlantica). The two fused rings exhibit different conformations: the six-membered ring has a screw-boat conformation, while the seven-membered ring displays a boat conformation. The dihedral angle between the two rings is 56.56 (18)°. In the crystal, mol-ecules aggregate into supra-molecular ...[more]

PMID: 21522372

Similar Datasets

(1S,3R,8R)-2,2-Dibromo-3,7,7,10-tetra-methyl-tricyclo-[6.4.0.0(1,3)]dodec-9-ene.

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(1S,3R,8R)-2,2-Di-chloro-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodec-9-en-11-one.

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(1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetra-methyl-9β,10β-ep-oxy-3,7,7,10-tetra-methyl-tricyclo-[6.4.0.0(1,3)]dodeca-ne.

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(1S,3R,8S,9R,10S)-2,2-Dichloro-3,7,7,10-tetra-methyl-9,10-ep-oxy-tricyclo-[6.4.0.0]dodeca-ne.

Project description:The title compound, C(16)H(24)Cl(2)O, was synthesized from ?-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from the essential oil of the Atlas cedar (cedrus atlantica). The mol-ecule forms an extended sheet of two fused rings which exhibit different conformations. The six-membered ring has a half-chair conformation, while the seven-membered ring displays a chair conformation; the dihedral angle between the two rings is 38.2?(1)°.

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(1S,3R,8R)-9-(1-Amino-ethyl-idene)-2,2-dichloro-3,7,7-trimethyl-tricyclo-[6.4.0.0]undecan-10-one.

Project description:The title compound, C(16)H(23)Cl(2)NO, was synthesised from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule contains a seven membered ring, which is fused to a five- and a three-membered ring. The five-membered ring has a twisted conformation, whereas the seven-membered ring displays a chair conformation. The dihedral angle between the five- and seven-membered rings is 45.26 (9)°. The absolute structure was established unambiguously from anomalous dispersion effects. In the crystal, mol-ecules are linked into chains propagating along the b axis by inter-molecular N-H⋯O hydrogen bonds; an intramolecular N-H⋯O link also occurs.

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Crystal structure of (1S,3R,8R,9R,10S)-2,4,6-tris-(2,2-di-chloro-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodec-9-yl)cyclo-triboroxane.

Project description:The title compound, C48H75B3Cl6O3, was synthesized in two steps from ?-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-hept-ene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule consists of an almost planar cyclo-triboroxane ring [maximum deviation = 0.036?(2)?Å] linked to three identical fused ring systems with different conformations. Each of the three attached ring systems is built up from a seven-membered ring to which a six- and a three-membered ring are fused. The three six-membered rings have a twist-boat conformation, whereas the seven-membered rings display boat, chair and twist-boat conformations. The dihedral angles between the central boroxane ring and the mean planes of the attached six-membered rings are 63.67?(18), 54.89?(2) and 56.57?(19)°. The crystal packing is governed only by van der Waals inter-actions.

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