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Volume 69 
Part 8 
Page o1261  
August 2013  

Received 4 July 2013
Accepted 9 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.010 Å
R = 0.042
wR = 0.095
Data-to-parameter ratio = 15.9
Details
Open access

(1S,3S,8R,9S,11R)-10,10-Dibromo-3,7,7,11-tetramethyltetracyclo[6.5.0.01,3.09,11]tridecane

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, Université MohammedV-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: berraho@uca.ma

The title compound, C17H26Br2, 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 asymmetric unit contains two independent molecules with similar conformations. Each molecule is built up from fused six- and seven-membered rings and two appended three-membered rings. In both molecules, the six-membered ring has a screw boat conformation, whereas the seven-membered ring displays a boat conformation. No specific intermolecular interactions were discerned in the crystal packing.

Related literature

For backgroud to Moroccan floral heritage, 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.]); Benharref et al. (2013[Benharref, A., El Karroumi, J., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o1037-o1038.]); Oukhrib et al. (2013[Oukhrib, A., Benharref, A., Saadi, M., Berraho, M. & El Ammari, L. (2013). Acta Cryst. E69, o521-o522.]). 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
  • C17H26Br2

  • Mr = 390.20

  • Monoclinic, P 21

  • a = 6.585 (7) Å

  • b = 29.05 (3) Å

  • c = 9.385 (9) Å

  • [beta] = 110.29 (2)°

  • V = 1684 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.80 mm-1

  • T = 296 K

  • 0.20 × 0.15 × 0.12 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.423, Tmax = 0.617

  • 11862 measured reflections

  • 5595 independent reflections

  • 4255 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.095

  • S = 1.10

  • 5595 reflections

  • 352 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.57 e Å-3

  • [Delta][rho]min = -0.34 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: 0.019 (12)

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: TK5238 ).


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]
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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1261  [ doi:10.1107/S160053681301903X ]

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