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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 [sigma](C-C) = 0.005 Å
R = 0.030
wR = 0.074
Data-to-parameter ratio = 18.9
Details
Open access

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

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[Joseph, T. C. & Dev, S. (1968). Tetrahedron, 24, 3841-3859.]); Plattier & Teiseire (1974[Plattier, M. & Teiseire, P. (1974). Recherche, 19, 131-144.]). For the reactivity of this sesquiterpene, see: Lassaba et al. (1997[Lassaba, E., Chekroun, A., Benharref, A., Chiaroni, A., Riche, C. & Lavergne, J.-P. (1997). Bull. Soc. Chim. Belg. 106, 281-288.]); Chekroun et al. (2000[Chekroun, A., Jarid, A., Benharref, A. & Boutalib, A. (2000). J. Org. Chem. 65, 4431-4434.]); El Jamili et al. (2002[El Jamili, H., Auhmani, A., Dakir, M., Lassaba, E., Benharref, A., Pierrot, M., Chiaroni, A. & Riche, C. (2002). Tetrahedron Lett. 43, 6645-6648.]); Sbai et al. (2002[Sbai, F., Dakir, M., Auhmani, A., El Jamili, H., Akssira, M., Benharref, A., Kenz, A. & Pierrot, M. (2002). Acta Cryst. C58, o518-o520.]); Dakir et al. (2004[Dakir, M., Auhmani, A., Ait Itto, M. Y., Mazoir, N., Akssira, M., Pierrot, M. & Benharref, A. (2004). Synth. Commun. 34, 2001-2008.]). For its biological activity, see: Daoubi et al. (2004[Daoubi, M., Duran-Patron, R., Hmamouchi, M., Hernandez-Galan, R., Benharref, A. & Isidro, G. C. (2004). Pest Manag. Sci. 60, 927-932.]). For conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C16H22Br2O

  • Mr = 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[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.259, Tmax = 0.746

  • 11891 measured reflections

  • 3330 independent reflections

  • 2939 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.074

  • S = 1.06

  • 3330 reflections

  • 176 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.68 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

  • Absolute structure: Flack (1983)[Flack, H. D. (1983). Acta Cryst. A39, 876-881.], 1397 Friedel pairs

  • Flack parameter: 0.021 (12)

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


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

Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chekroun, A., Jarid, A., Benharref, A. & Boutalib, A. (2000). J. Org. Chem. 65, 4431-4434.  [CrossRef] [PubMed] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Dakir, M., Auhmani, A., Ait Itto, M. Y., Mazoir, N., Akssira, M., Pierrot, M. & Benharref, A. (2004). Synth. Commun. 34, 2001-2008.  [ISI] [CrossRef] [ChemPort]
Daoubi, M., Duran-Patron, R., Hmamouchi, M., Hernandez-Galan, R., Benharref, A. & Isidro, G. C. (2004). Pest Manag. Sci. 60, 927-932.  [CrossRef] [PubMed] [ChemPort]
El Jamili, H., Auhmani, A., Dakir, M., Lassaba, E., Benharref, A., Pierrot, M., Chiaroni, A. & Riche, C. (2002). Tetrahedron Lett. 43, 6645-6648.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Joseph, T. C. & Dev, S. (1968). Tetrahedron, 24, 3841-3859.  [CrossRef] [ChemPort] [ISI]
Lassaba, E., Chekroun, A., Benharref, A., Chiaroni, A., Riche, C. & Lavergne, J.-P. (1997). Bull. Soc. Chim. Belg. 106, 281-288.  [ChemPort]
Plattier, M. & Teiseire, P. (1974). Recherche, 19, 131-144.  [ChemPort]
Sbai, F., Dakir, M., Auhmani, A., El Jamili, H., Akssira, M., Benharref, A., Kenz, A. & Pierrot, M. (2002). Acta Cryst. C58, o518-o520.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3341-o3342   [ doi:10.1107/S1600536812046089 ]

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