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Volume 69 
Part 8 
Pages o1308-o1309  
August 2013  

Received 18 June 2013
Accepted 3 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.037
wR = 0.098
Data-to-parameter ratio = 14.0
Details
Open access

Absolute configuration of (1R,3S,8R,11R)-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodec-9-en-11-ol

aLaboratoire de Physico-Chimie Moléculaire et Synthése Organique, Département de Chimie, Faculté des Sciences, Semlalia BP 2390, Marrakech 40001, Morocco, and bLaboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France
Correspondence e-mail: itto35@hotmail.com_or_aititto@uca.ma

The absolute configuration of the title compound, C16H26O, was determined as (1R,3S,8R,11R) based mainly on the synthetic pathway but is also implied by the X-ray analysis. The molecule contains fused six- and seven-membered rings. Part of the seven-membered ring was refined as disordered over two sets of sites with the occupancy ratio fixed at 0.86:0.14. The disorder corresponds to a major chair conformation and a minor boat conforation. In the crysyal, O-H...O hydrogen bonds connect the molecules into chains parallel to the a axis.

Related literature

For related structures, see: Benharref et al. (2010[Benharref, A., El Ammari, L., Berraho, M. & Lassaba, E. (2010). Acta Cryst. E66, o2463.]); Gassman & Goman (1990[Gassman, P. G. & Goman, D. B. (1990). J. Am. Chem. Soc. 112, 8623.]); Lassaba et al. (1997[Lassaba, E., Benharref, A., Giorgi, M. & Pierrot, M. (1997). Acta Cryst. C53, 1943-1945.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Boessenkool & Boyens (1980[Boessenkool, I. K. & Boyens, J. C. A. (1980). J. Cryst. Mol. Struct. 10, 11-18.]). For Bijvoet pair analysis, see: Hooft et al. (2008[Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.]). For analysis of the absolute structure, see: Flack & Bernardinelli (2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]). For chemical properties of related compounds, see: Paresh & Sujit (2012[Paresh, N. C. & Sujit, R. (2012). Tetrahedron, 68, 3776-3785.]); Arfaoui et al. (2010[Arfaoui, J., Boudali, L. K. & Ghorbel, A. (2010). Appl. Clay Sci. 48, 171-178.]). For their biological properties, see: Chung et al. (2007[Chung, I., Kwon, S. H., Shim, S.-T. & Kyung, K. H. (2007). J. Food Sci. 72, 437-440.]); Servi et al. (2000[Servi, S., Cansiz, A., Digrak, M. & Ahmedzade, M. (2000). Indian J. Chem. Sect. B, 39, 629-633.]). For the synthesis, see: Auhmani et al. (2001[Auhmani, A., Kossareva, E., Eljamili, H., Reglier, M., Pierrot, M. & Benharref, A. (2001). Acta Cryst. E57, o102-o103.]).

[Scheme 1]

Experimental

Crystal data
  • C16H26O

  • Mr = 234.37

  • Orthorhombic, P 21 21 21

  • a = 6.1457 (1) Å

  • b = 8.2466 (2) Å

  • c = 27.4454 (7) Å

  • V = 1390.96 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.51 mm-1

  • T = 173 K

  • 0.32 × 0.13 × 0.07 mm

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

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.863, Tmax = 1.000

  • 8172 measured reflections

  • 2653 independent reflections

  • 2539 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.04

  • 2653 reflections

  • 190 parameters

  • 29 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]) 1059 Friedel pairs

  • Flack parameter: -0.1 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O1i 0.89 (1) 2.32 (1) 3.1612 (6) 159 (2)
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]), 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5626 ).


References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Arfaoui, J., Boudali, L. K. & Ghorbel, A. (2010). Appl. Clay Sci. 48, 171-178.  [CrossRef] [ChemPort]
Auhmani, A., Kossareva, E., Eljamili, H., Reglier, M., Pierrot, M. & Benharref, A. (2001). Acta Cryst. E57, o102-o103.  [CrossRef] [ChemPort] [IUCr Journals]
Benharref, A., El Ammari, L., Berraho, M. & Lassaba, E. (2010). Acta Cryst. E66, o2463.  [CrossRef] [IUCr Journals]
Boessenkool, I. K. & Boyens, J. C. A. (1980). J. Cryst. Mol. Struct. 10, 11-18.  [CrossRef] [ChemPort]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Chung, I., Kwon, S. H., Shim, S.-T. & Kyung, K. H. (2007). J. Food Sci. 72, 437-440.  [CrossRef]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gassman, P. G. & Goman, D. B. (1990). J. Am. Chem. Soc. 112, 8623.  [CrossRef]
Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Lassaba, E., Benharref, A., Giorgi, M. & Pierrot, M. (1997). Acta Cryst. C53, 1943-1945.  [CrossRef] [IUCr Journals]
Paresh, N. C. & Sujit, R. (2012). Tetrahedron, 68, 3776-3785.
Servi, S., Cansiz, A., Digrak, M. & Ahmedzade, M. (2000). Indian J. Chem. Sect. B, 39, 629-633.
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, o1308-o1309   [ doi:10.1107/S1600536813018497 ]

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