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Volume 69 
Part 12 
Pages o1777-o1778  
December 2013  

Received 6 November 2013
Accepted 11 November 2013
Online 16 November 2013

Key indicators
Single-crystal X-ray study
T = 180 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.022
wR = 0.057
Data-to-parameter ratio = 11.7
Details
Open access

(1S,3R,8R,10R)-2,2-Di­bromo-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.01,3]dodecan-9-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, C16H24Br2O was synthesized by 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 mol­ecule is built up from a seven-membered ring to which a six- and a three-membered ring are fused. The six-membered ring shows a chair conformation. One C atom in the seven-membered ring and two methyl groups attached to the ring are disordered over two sets of sites, with an occupancy ratio of 0.658 (7):0.342 (7).

Related literature

For background to the reactivity and biological properties of [beta]-himachalene, see: El Haib et al. (2011[El Haib, A., Benharref, A., Parres-Maynadié, S., Manoury, E., Urrutigoïty, 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.]). For related structures, see: Benharref et al. (2013[Benharref, A., Ourhriss, N., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o933-o934.]); 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 conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C16H24Br2O

  • Mr = 392.17

  • Monoclinic, P 21

  • a = 6.5975 (2) Å

  • b = 15.2612 (3) Å

  • c = 8.2688 (2) Å

  • [beta] = 100.045 (3)°

  • V = 819.79 (4) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 6.19 mm-1

  • T = 180 K

  • 0.5 × 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 = 0.269, Tmax = 1.000

  • 6201 measured reflections

  • 2416 independent reflections

  • 2399 reflections with I > 2[sigma](I)

  • Rint = 0.021

  • [theta]max = 60.5°

Refinement
  • R[F2 > 2[sigma](F2)] = 0.022

  • wR(F2) = 0.057

  • S = 1.07

  • 2416 reflections

  • 206 parameters

  • 13 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

  • Absolute structure: Flack & Bernardinelli (2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]), 1127 Friedel pairs

  • Absolute structure parameter: 0.01 (2)

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: BT6944 ).


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]
El Haib, A., Benharref, A., Parres-Maynadié, S., Manoury, E., Urrutigoïty, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101-108.  [Web of Science] [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.  [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.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Ourhriss, N., Benharref, A., Saadi, M., El Ammari, L. & Berraho, M. (2013). Acta Cryst. E69, o275.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1777-o1778   [ doi:10.1107/S1600536813030936 ]

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