(1S,3R,8R)-2,2-Dibromo-10-bromo­methyl-3,7,7-trimethyl­tricyclo­[6.4.0.01,3]dodec-9-ene

Oukhrib, A.; Benharref, A.; Saadi, M.; Daran, J.-C.; Berraho, M.

doi:10.1107/S1600536812046430

Volume 68
Part 12
Pages o3394-o3395
December 2012

Received 6 November 2012
Accepted 9 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.006 Å
R = 0.034
wR = 0.075
Data-to-parameter ratio = 19.7
Details

(1S,3R,8R)-2,2-Dibromo-10-bromomethyl-3,7,7-trimethyltricyclo[6.4.0.0^1,3]dodec-9-ene

Abdelouahd Oukhrib,^a ^* Ahmed Benharref,^a Mohamed Saadi,^b Jean-Claude Daran ^c 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,^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Avenue Ibn Battouta, BP 1014 Rabat, Morocco, and ^cLaboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France
Correspondence e-mail: berraho@uca.ma

The title compound, C₁₆H₂₃Br₃, 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 (the flap atom being the C atom shared with the three-membered ring, whereas the seven-membered ring displays a screw boat conformation; the dihedral angle between the rings (defined by the near coplanar atoms) is 56.5 (2)°.

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); Benharref et al. (2010). For its biological activity, see: Daoubi et al. (2004). For conformational analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₆H₂₃Br₃
M_r = 455.07
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.2614 (5) Å
b = 12.8215 (8) Å
c = 14.3966 (11) Å
V = 1709.52 (19) Å³
Z = 4
Mo K radiation
= 7.07 mm^-1
T = 180 K
0.49 × 0.31 × 0.08 mm

Data collection

Agilent Xcalibur (Sapphire1, long nozzle) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.135, T_max = 1.000
9721 measured reflections
3461 independent reflections
3121 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.075
S = 1.04
3461 reflections
176 parameters
H-atom parameters constrained
_max = 0.66 e Å^-3
_min = -0.55 e Å^-3
Absolute structure: Flack (1983), 1460 Friedel pairs
Flack parameter: 0.012 (16)

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: IM2411 ).

Acknowledgements

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

References

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