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Volume 69 
Part 6 
Pages o933-o934  
June 2013  

Received 9 May 2013
Accepted 15 May 2013
Online 22 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.050
wR = 0.123
Data-to-parameter ratio = 17.0
Details
Open access

(1S,3S,8R,9S,11R)-10,10-Dichloro-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: n_ourhriss@yahoo.fr

The title compound, C17H26Cl2, 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 three-membered rings from the reaction of [beta]-himachalene with dichlorocarbene. In both molecules, the six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. The absolute configuration was established from anomalous dispersion effects.

Related literature

For the reactivity and biological properties of [beta]-himachalene, see: El Haib et al. (2011[El Haib, A., Benharref, A., Parrès-Maynadié, 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.]); Auhmani et al. (2002[Auhmani, A., Kossareva, E., Eljamili, H., Reglier, M., Pierrot, M. & Benharref, A. (2002). Synth. Commun. 32, 699-707.]). 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.]). 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
  • C17H26Cl2

  • Mr = 301.28

  • Monoclinic, P 21

  • a = 6.4930 (2) Å

  • b = 29.0000 (8) Å

  • c = 9.2854 (4) Å

  • [beta] = 110.454 (1)°

  • V = 1638.18 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.38 mm-1

  • T = 296 K

  • 0.45 × 0.35 × 0.30 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 10017 measured reflections

  • 5832 independent reflections

  • 5438 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.123

  • S = 1.09

  • 5832 reflections

  • 343 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

  • Absolute structure: Flack & Bernardinelli (2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]), 1283 Friedel pairs

  • Flack parameter: 0.05 (6)

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: RZ5066 ).


Acknowledgements

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

References

Auhmani, A., Kossareva, E., Eljamili, H., Reglier, M., Pierrot, M. & Benharref, A. (2002). Synth. Commun. 32, 699-707.  [ISI] [CrossRef] [ChemPort]
Bruker (2009). APEX2 and SAINT. 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., Urrutigoity, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101-108.  [ISI] [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.  [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. (2013). Acta Cryst. E69, o521-o522.  [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]


Acta Cryst (2013). E69, o933-o934   [ doi:10.1107/S1600536813013457 ]

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