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Volume 69 
Part 5 
Page o724  
May 2013  

Received 26 March 2013
Accepted 3 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
R = 0.038
wR = 0.092
Data-to-parameter ratio = 19.6
Details
Open access

(1S,3R,8R,9S,11R)-2,2-Dibromo-10,10-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 molecule contains fused six-, seven- and two three-membered rings. The six-membered ring has a half-chair conformation, while the seven-membered ring displays a boat conformation. The absolute structure was unambiguously established from anomalous dispersion effects. The crystal packing exhibits no short intermolecular contacts.

Related literature

For the crystal structures of related 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 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, P 21

  • a = 9.0112 (6) Å

  • b = 11.6772 (8) Å

  • c = 9.0849 (6) Å

  • [beta] = 108.045 (5)°

  • V = 908.94 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 4.75 mm-1

  • T = 296 K

  • 0.45 × 0.34 × 0.29 mm

Data collection
  • Bruker X8 APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.739, Tmax = 0.867

  • 6676 measured reflections

  • 3720 independent reflections

  • 2910 reflections with I > 2[sigma](I)

  • Rint = 0.034

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

  • wR(F2) = 0.092

  • S = 1.03

  • 3720 reflections

  • 190 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.64 e Å-3

  • [Delta][rho]min = -0.79 e Å-3

  • Absolute structure: Flack & Bernardinelli (2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]), 1096 Friedel pairs

  • Flack parameter: 0.039 (10)

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: CV5397 ).


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]
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, o724  [ doi:10.1107/S1600536813009070 ]

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