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Volume 69 
Part 4 
Pages o521-o522  
April 2013  

Received 2 March 2013
Accepted 3 March 2013
Online 9 March 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.033
wR = 0.074
Data-to-parameter ratio = 26.8
Details
Open access

(1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetramethyl-9[beta],10[beta]-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodecane

aLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité "Unité Associée 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, Avenue Ibn Battouta, BP 1014 Rabat, Morocco
Correspondence e-mail: berraho@uca.ma

The title compound, C16H24Br2O, 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- and seven-membered rings, each linked to a three-membered ring. The six-membered ring has a half-chair conformation, while the seven-membered ring displays a chair conformation. The dihedral angle between the mean planes through the six- and seven-membered rings is 39.55 (12)°. The two three-membered rings, linked to the six- and seven-membered rings, are nearly perpendicular to the six-membered ring, making dihedral angles of 78.6 (2) and 80.5 (2)°, respectively. The absolute structure was established unambiguously from anomalous dispersion effects. In the crystal, each molecule is linked to its symmetry-equivalent partner by C-H...O hydrogen bonds, forming zigzag chains parallel to [100].

Related literature

For the isolation of [beta]-himachalene, see: Joseph & Dev (1968[Joseph, T. C. & Dev, S. (1968). Tetrahedron, 24, 3841-3859.]); Plattier & Teisseire (1974[Plattier, M. & Teisseire, P. (1974). Recherche, 19, 131-144.]). For the reactivity of this sesquiterpene, see: Lassaba et al. (1998[Lassaba, E., Eljamili, H., Chekroun, A., Benharref, A., Chiaroni, A., Riche, C. & Lavergne, J.-P. (1998). Synth. Commun. 28, 2641-2651.]); Chekroun et al. (2000[Chekroun, A., Jarid, A., Benharref, A. & Boutalib, A. (2000). J. Org. Chem. 65, 4431-4434.]); 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.]); Sbai et al. (2002[Sbai, F., Dakir, M., Auhmani, A., El Jamili, H., Akssira, M., Benharref, A., Kenz, A. & Pierrot, M. (2002). Acta Cryst. C58, o518-o520.]); Dakir et al. (2004[Dakir, M., Auhmani, A., Ait Itto, M. Y., Mazoir, N., Akssira, M., Pierrot, M. & Benharref, A. (2004). Synth. Commun. 34, 2001-2008.]). For its biological activity, see: Daoubi et al. (2004[Daoubi, M., Duran-Patron, R., Hmamouchi, M., Hernandez-Galan, R., Benharref, A. & Isidro, G. C. (2004). Pest Manag. Sci. 60, 927-932.]). For ring puckering calculations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For a similar structure, see: Benharref et al. (2010[Benharref, A., El Ammari, L., Avignant, D., Oudahmane, A. & Berraho, M. (2010). Acta Cryst. E66, o3125.]).

[Scheme 1]

Experimental

Crystal data
  • C16H24Br2O

  • Mr = 392.17

  • Orthorhombic, P 21 21 21

  • a = 7.9772 (4) Å

  • b = 12.8562 (7) Å

  • c = 16.1719 (8) Å

  • V = 1658.53 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.88 mm-1

  • T = 296 K

  • 0.41 × 0.32 × 0.27 mm

Data collection
  • Bruker X8 APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.407, Tmax = 0.747

  • 15200 measured reflections

  • 4637 independent reflections

  • 3298 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.074

  • S = 1.02

  • 4637 reflections

  • 173 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 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.]), 1998 Friedel pairs

  • Flack parameter: 0.014 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9...O1i 0.98 2.53 3.391 (3) 146
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z].

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: FJ2620 ).


Acknowledgements

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

References

Benharref, A., El Ammari, L., Avignant, D., Oudahmane, A. & Berraho, M. (2010). Acta Cryst. E66, o3125.  [CSD] [CrossRef] [details]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chekroun, A., Jarid, A., Benharref, A. & Boutalib, A. (2000). J. Org. Chem. 65, 4431-4434.  [CrossRef] [PubMed] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Dakir, M., Auhmani, A., Ait Itto, M. Y., Mazoir, N., Akssira, M., Pierrot, M. & Benharref, A. (2004). Synth. Commun. 34, 2001-2008.  [ISI] [CrossRef] [ChemPort]
Daoubi, M., Duran-Patron, R., Hmamouchi, M., Hernandez-Galan, R., Benharref, A. & Isidro, G. C. (2004). Pest Manag. Sci. 60, 927-932.  [CrossRef] [PubMed] [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]
Joseph, T. C. & Dev, S. (1968). Tetrahedron, 24, 3841-3859.  [CrossRef] [ChemPort] [ISI]
Lassaba, E., Eljamili, H., Chekroun, A., Benharref, A., Chiaroni, A., Riche, C. & Lavergne, J.-P. (1998). Synth. Commun. 28, 2641-2651.  [ISI] [CrossRef] [ChemPort]
Plattier, M. & Teisseire, P. (1974). Recherche, 19, 131-144.  [ChemPort]
Sbai, F., Dakir, M., Auhmani, A., El Jamili, H., Akssira, M., Benharref, A., Kenz, A. & Pierrot, M. (2002). Acta Cryst. C58, o518-o520.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o521-o522   [ doi:10.1107/S1600536813006077 ]

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