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Volume 69 
Part 11 
Page o1703  
November 2013  

Received 7 October 2013
Accepted 20 October 2013
Online 26 October 2013

Key indicators
Single-crystal X-ray study
T = 180 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.070
Data-to-parameter ratio = 18.0
Details
Open access

(1R,4R,6S,7S)-5,5-Di­chloro-1,4,8,8-tetra­methyl­tri­cyclo­[5.4.11,7.04,6]dodecan-12-one

aLaboratoire de Chimie Biomoléculaires, Substances Naturelles et Réactivité, URAC16, Faculté des Sciences, Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, and bLaboratoire de Chimie de Coordination, 205 Route de Narbone, 31077 Toulouse Cedex 04, France
Correspondence e-mail: berraho@uca.ma

The title compound, C16H24Cl2O, was synthesized in three steps from [beta]-himachalene (3,5,5,9-tetra­methyl-2,4a,5,6,7,8-hexa­hydro-1H-benzo­cyclo­heptene), which was isolated from essential oil of the Atlas cedar (cedrus atlantica). The asymmetric unit contains two independent mol­ecules with similar conformations. Each mol­ecule is built up from two fused seven-membered rings and an additional three-membered ring arising from the reaction of himachalene with di­chloro­carbene. The dihedral angles between the mean planes of the two seven-membered rings are 75.03 (9) and 75.02 (9)° in the two independent mol­ecules.

Related literature

For the reactivity of this sesquiterpene, see: 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.]); Lassaba et al. (1997[Lassaba, E., Benharref, A., Giorgi, M. & Pierrot, M. (1997). Acta Cryst. C53, 1943-1945.]). For its biological activity, see: Elhaib et al. (2011[Elhaib, A., Benharref, A., Parrès-Maynadié, S., Manoury, E., Urrutigoïty, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101-108.]). For a related structure, see: Benharref et al. (2013[Benharref, A., Ourhriss, N., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o933-o934.]). 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
  • C16H24Cl2O

  • Mr = 303.25

  • Triclinic, P 1

  • a = 6.5835 (2) Å

  • b = 9.2584 (3) Å

  • c = 12.8428 (5) Å

  • [alpha] = 85.140 (3)°

  • [beta] = 84.795 (3)°

  • [gamma] = 89.067 (3)°

  • V = 776.74 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.41 mm-1

  • T = 180 K

  • 0.50 × 0.03 × 0.03 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO . Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.822, Tmax = 0.988

  • 15959 measured reflections

  • 6301 independent reflections

  • 5899 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.070

  • S = 1.05

  • 6301 reflections

  • 351 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

  • Absolute structure: Flack & Bernardinelli (2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]), 3127 Friedel pairs

  • Absolute structure parameter: 0.05 (3)

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO . Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: BT6937 ).


References

Agilent (2013). CrysAlis PRO . Agilent Technologies Ltd, Yarnton, England.
Benharref, A., Ourhriss, N., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o933-o934.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Elhaib, A., Benharref, A., Parrès-Maynadié, S., Manoury, E., Urrutigoïty, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101-108.  [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]
Lassaba, E., Benharref, A., Giorgi, M. & Pierrot, M. (1997). Acta Cryst. C53, 1943-1945.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1703  [ doi:10.1107/S1600536813028791 ]

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