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Volume 69 
Part 8 
Page o1283  
August 2013  

Received 15 July 2013
Accepted 16 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.038
wR = 0.102
Data-to-parameter ratio = 19.9
Details
Open access

(1S,3R,8R,11S)-11-Bromo-10-bromomethyl-2,2-dichloro-3,7,7-trimethyltricyclo[6.4.0.01,3]dodec-9-ene

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, Université MohammedV-Agdal , Avenue Ibn Battouta, BP 1014, Rabat, Morocco, and cLaboratoire de Chimie du Solide, Appliquée, Faculté des Sciences, Université MohammedV-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: berraho@uca.ma

The title compound, C16H22Br2Cl2, 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 appended three-membered ring. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a chair conformation. The dihedral angle between the two best plane through each ring is 59.5 (2)°. No specific intermolecular interactions were discerned in the crystal packing.

Related literature

For the reactivity and biological properties of [beta]-himachalene, see: El Haib et al. (2011[El Haib, A., Benharref, A., Parres-Maynadie, S., Manoury, E., Urrutigoity, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101-108.]); 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.]); 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 related structures, see: Oukhrib et al. (2013[Oukhrib, A., Benharref, A., Saadi, M., Berraho, M. & El Ammari, L. (2013). Acta Cryst. E69, o521-o522.]); Ourhriss et al. (2013[Ourhriss, N., Benharref, A., Saadi, M., El Ammari, L. & Berraho, M. (2013). Acta Cryst. E69, o275.]); Benharref et al.(2013[Benharref, A., El Karroumi, J., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o1037-o1038.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C16H22Br2Cl2

  • Mr = 445.06

  • Orthorhombic, P 21 21 21

  • a = 8.2594 (7) Å

  • b = 13.0352 (11) Å

  • c = 16.6241 (13) Å

  • V = 1789.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.82 mm-1

  • T = 293 K

  • 0.20 × 0.15 × 0.12 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SHELXS97; Sheldrick,2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.423, Tmax = 0.617

  • 10693 measured reflections

  • 3654 independent reflections

  • 3183 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.102

  • S = 1.05

  • 3654 reflections

  • 184 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.54 e Å-3

  • Absolute structure: Flack & Bernardinelli (2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]), 614 Friedel pairs

  • Absolute structure parameter: 0.022 (13)

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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: TK5241 ).


Acknowledgements

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

References

Benharref, A., El Karroumi, J., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o1037-o1038.  [CrossRef] [ChemPort] [IUCr Journals]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
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 Haib, A., Benharref, A., Parres-Maynadie, S., Manoury, E., Urrutigoity, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101-108.  [Web of Science] [CrossRef] [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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Oukhrib, A., Benharref, A., Saadi, M., Berraho, M. & El Ammari, L. (2013). Acta Cryst. E69, o521-o522.  [CrossRef] [ChemPort] [IUCr Journals]
Ourhriss, N., Benharref, A., Saadi, M., El Ammari, L. & Berraho, M. (2013). Acta Cryst. E69, o275.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1283  [ doi:10.1107/S1600536813019697 ]

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