(1S,3R,8R)-2,2-Dibromo-3,7,7,10-tetra­methyltricyclo­[6.4.0.01,3]dodec-9-en-11-one

Oukhrib, A.; Benharref, A.; Saadi, M.; El Ammari, L.; Berraho, M.

doi:10.1107/S1600536812046089

Volume 68
Part 12
Pages o3341-o3342
December 2012

Received 29 October 2012
Accepted 7 November 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.030
wR = 0.074
Data-to-parameter ratio = 18.9
Details

(1S,3R,8R)-2,2-Dibromo-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-9-en-11-one

Abdelouahd Oukhrib,^a ^* Ahmed Benharref,^a Mohamed Saadi,^b Lahcen El Ammari ^b and Moha Berraho ^a

^aLaboratoire de Chimie des Substances Naturelles, "Unité Associé au CNRST (URAC16)", Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Avenue Ibn Battouta, BP 1014 Rabat, Morocco
Correspondence e-mail: berraho@uca.ma

The title compound, C₁₆H₂₂Br₂O, was synthesized from [beta] -himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzocycloheptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The molecule is built up from fused six- and seven-membered rings and an additional three-membered ring from the reaction of himachalene with dibromocarbene. The six-membered ring has an envelope conformation, with the C atom belonging to the three-membered ring forming the flap, whereas the seven-membered ring displays a screw-boat conformation; the dihedral angle between the rings (all atoms) is 60.92 (16)°.

Related literature

For the isolation of [beta] -himachalene, see: Joseph & Dev (1968); Plattier & Teiseire (1974). For the reactivity of this sesquiterpene, see: Lassaba et al. (1997); Chekroun et al. (2000); El Jamili et al. (2002); Sbai et al. (2002); Dakir et al. (2004). For its biological activity, see: Daoubi et al. (2004). For conformational analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₆H₂₂Br₂O
M_r = 390.16
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.7369 (1) Å
b = 14.7635 (3) Å
c = 16.3543 (3) Å
V = 1626.60 (5) Å³
Z = 4
Mo K radiation
= 4.98 mm^-1
T = 298 K
0.80 × 0.65 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.259, T_max = 0.746
11891 measured reflections
3330 independent reflections
2939 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.074
S = 1.06
3330 reflections
176 parameters
H-atom parameters constrained
_max = 0.68 e Å^-3
_min = -0.37 e Å^-3
Absolute structure: Flack (1983), 1397 Friedel pairs
Flack parameter: 0.021 (12)

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2074 ).

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

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