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Volume 70 
Part 1 
Pages o81-o82  
January 2014  

Received 4 October 2013
Accepted 17 December 2013
Online 21 December 2013

Key indicators
Single-crystal X-ray study
T = 180 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.111
Data-to-parameter ratio = 31.0
Details
Open access

(1R,3S,8R)-3,7,7,10-Tetra­methyl­tri­cyclo­[6.4.0.01,3]dodec-9-en-11-one

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: a.auhmani@uca.ma

The absolute configuration of the title compound, C16H24O, has been deduced from the chemical pathway. The six-membered ring has a roughly half-chair conformation with the quaternary C atom as the flap. The seven-membered ring displays a chair conformation. In the crystal, there is a weak C-H...O hydrogen bond between the methyl­ene group of the cyclo­propane ring and the carbonyl group of a screw-axis-related mol­ecule, which builds up a zigzag-like chain along the b-axis direction.

Related literature

For related structures, see: Benharref et al. (2012[Benharref, A., El Ammari, L., Lassaba, E., Ourhriss, N. & Berraho, M. (2012). Acta Cryst. E68, o2502.]); Gassman & Gorman (1990[Gassman, P. G. & Gorman, 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 ring puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For structural discussion, see: Evans & Boeyens (1989[Evans, D. G. & Boeyens, J. C. A. (1989). Acta Cryst. B45, 581-590.]); Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). For chemical properties, see: Auhmani et al. (2002[Auhmani, A., Kossareva, E., Eljamili, H., Reglier, M., Pierrot, M. & Benharref, A. (2002). Synth. Commun. 32, 707-715.]); Danyang et al. (2007[Danyang, L., Bastiaan, J. V., Hakan, V. W. & Durk, D. (2007). Tetrahedron, 63, 7264-7270.]); Tetsuhiro et al. (2003[Tetsuhiro, N., Takashi, O. & Masakatsu, S. (2003). Tetrahedron, 59, 6889-6897.]).

[Scheme 1]

Experimental

Crystal data
  • C16H24O

  • Mr = 232.35

  • Monoclinic, P 21

  • a = 6.4379 (2) Å

  • b = 7.8889 (3) Å

  • c = 13.5122 (5) Å

  • [beta] = 97.430 (2)°

  • V = 680.49 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 180 K

  • 0.38 × 0.23 × 0.08 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.661, Tmax = 0.747

  • 15568 measured reflections

  • 4902 independent reflections

  • 4331 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.111

  • S = 1.04

  • 4902 reflections

  • 158 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2B...O1i 0.99 2.60 3.541 (2) 160
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXL2013 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). 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 Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL2013.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2107 ).


References

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]
Auhmani, A., Kossareva, E., Eljamili, H., Reglier, M., Pierrot, M. & Benharref, A. (2002). Synth. Commun. 32, 707-715.
Benharref, A., El Ammari, L., Lassaba, E., Ourhriss, N. & Berraho, M. (2012). Acta Cryst. E68, o2502.  [CSD] [CrossRef] [IUCr Journals]
Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Danyang, L., Bastiaan, J. V., Hakan, V. W. & Durk, D. (2007). Tetrahedron, 63, 7264-7270.
Evans, D. G. & Boeyens, J. C. A. (1989). Acta Cryst. B45, 581-590.  [CrossRef] [Web of Science] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gassman, P. G. & Gorman, D. B. (1990). J. Am. Chem. Soc. 112, 8623.  [CSD] [CrossRef] [Web of Science]
Lassaba, E., Benharref, A., Giorgi, M. & Pierrot, M. (1997). Acta Cryst. C53, 1943-1945.  [CSD] [CrossRef] [IUCr Journals]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). 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]
Tetsuhiro, N., Takashi, O. & Masakatsu, S. (2003). Tetrahedron, 59, 6889-6897.


Acta Cryst (2014). E70, o81-o82   [ doi:10.1107/S1600536813034041 ]

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