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Volume 69 
Part 8 
Page o1350  
August 2013  

Received 22 July 2013
Accepted 24 July 2013
Online 31 July 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.102
Data-to-parameter ratio = 10.8
Details
Open access

(1S,3S,8R,10R,11R)-3,7,7,10-Tetramethyltricyclo[6.4.0.01,3]dodecan-11-ol

aLaboratoire de Chimie Biomoléculaires, Substances Naturelles et Réactivité, URAC16, Faculté des Sciences, Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco,bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université MohammedV-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco, and cLaboratoire de Chimie des Substances Naturelles `Unité Associé au CNRST (URAC16)', Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco
Correspondence e-mail: berraho@uca.ma

The title compound, C16H28O, 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 the essential oil of the Atlas cedar (Cedrus atlantica). The molecule is built up from fused six- and seven-membered rings and an appended three-membered ring. The six-membered ring has twist-boat conformation, whereas the seven-membered ring displays a chair conformation. In the crystal, molecules are linked into chains propagating along the a-axis direction by O-H...O hydrogen bonds.

Related literature

For the reactivity and biological properties of [beta]-himachalene, see: Auhmani et al.(2002[Auhmani, A., Kossareva, E., Eljamili, H., Reglier, M., Pierrot, M. & Benharref, A. (2002). Synth. Commun. 32, 699-707.]); 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.]); 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 related structures, see: Ourhriss et al. (2013[Ourhriss, N., Benharref, A., Saadi, M., El Ammari, L. & Berraho, M. (2013). Acta Cryst. E69, o275.]); Benharref et al. (2013[Benharref, A., Ourhriss, N., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o933-o934.]). 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
  • C16H28O

  • Mr = 236.38

  • Orthorhombic, P 21 21 21

  • a = 5.8796 (2) Å

  • b = 12.7822 (4) Å

  • c = 19.1496 (7) Å

  • V = 1439.17 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 298 K

  • 0.25 × 0.15 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 8482 measured reflections

  • 1724 independent reflections

  • 1485 reflections with I > 2[sigma](I)

  • Rint = 0.030

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

  • wR(F2) = 0.102

  • S = 1.03

  • 1724 reflections

  • 160 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O1i 0.82 2.35 3.139 (3) 163
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{5\over 2}}, -z].

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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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: BT6923 ).


Acknowledgements

We thank the National Center of Scientific and Technological Research (CNRST) which supports our scientific research.

References

Auhmani, A., Kossareva, E., Eljamili, H., Reglier, M., Pierrot, M. & Benharref, A. (2002). Synth. Commun. 32, 699-707.  [Web of Science] [CrossRef] [ChemPort]
Benharref, A., Ourhriss, N., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o933-o934.  [CrossRef] [ChemPort] [IUCr Journals]
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] [Web of Science]
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.  [Web of Science] [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]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1350  [ doi:10.1107/S1600536813020576 ]

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