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Volume 69 
Part 5 
Page o739  
May 2013  

Received 4 April 2013
Accepted 11 April 2013
Online 17 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.041
wR = 0.103
Data-to-parameter ratio = 24.2
Details
Open access

(1S,3R,8R,9S,11R)-10,10-Dibromo-2,2-dichloro-3,7,7,11-tetramethyltetracyclo[6.5.0.01,3.09,11]tridecane

aLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité, Unité Associée au CNRST (URAC16)", Université Cadi Ayyad, Faculté des Sciences Semlalia, BP 2390, Bd My Abdellah, 40000 Marrakech, Morocco, and bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: berraho@uca.ma

The title compound, C17H24Br2Cl2, 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. Each molecule is built up from fused six-, seven- and two three-membered rings. In both molecules, the six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. No specific intermolecular interactions are noted in the crystal packing.

Related literature

For similar compounds, see: Ourhriss et al. (2013[Ourhriss, N., Benharref, A., Saadi, M., El Ammari, L. & Berraho, M. (2013). Acta Cryst. E69, o275.]); Oukhrib et al. (2013a[Oukhrib, A., Benharref, A., Saadi, M., Berraho, M. & El Ammari, L. (2013a). Acta Cryst. E69, o521-o522.],b[Oukhrib, A., Benharref, A., Saadi, M., Berraho, M. & El Ammari, L. (2013b). Acta Cryst. E69, o589-o590.]). For the biological proprieties of [beta]-himachalene, see: El Haib et al. (2011[El Haib, A., Benharref, A., Parrès-Maynadié, S., Manoury, E., Urrutigoïty, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101-108.]). 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
  • C17H24Br2Cl2

  • Mr = 459.08

  • Monoclinic, C 2

  • a = 18.377 (16) Å

  • b = 6.519 (6) Å

  • c = 30.82 (3) Å

  • [beta] = 93.233 (16)°

  • V = 3687 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 4.68 mm-1

  • T = 296 K

  • 0.43 × 0.31 × 0.27 mm

Data collection
  • Bruker X8 APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.739, Tmax = 0.867

  • 40489 measured reflections

  • 9155 independent reflections

  • 6959 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.103

  • S = 1.04

  • 9155 reflections

  • 379 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.67 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

  • Absolute structure: Flack & Bernardinelli (2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]), 3988 Friedel pairs

  • Flack parameter: 0.029 (8)

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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2192 ).


Acknowledgements

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

References

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] [ISI]
El Haib, A., Benharref, A., Parrès-Maynadié, S., Manoury, E., Urrutigoïty, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101-108.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.  [ISI] [CrossRef] [ChemPort] [details]
Oukhrib, A., Benharref, A., Saadi, M., Berraho, M. & El Ammari, L. (2013a). Acta Cryst. E69, o521-o522.  [CrossRef] [ChemPort] [details]
Oukhrib, A., Benharref, A., Saadi, M., Berraho, M. & El Ammari, L. (2013b). Acta Cryst. E69, o589-o590.  [CrossRef] [ChemPort] [details]
Ourhriss, N., Benharref, A., Saadi, M., El Ammari, L. & Berraho, M. (2013). Acta Cryst. E69, o275.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o739  [ doi:10.1107/S1600536813010040 ]

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