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Volume 69 
Part 5 
Page o799  
May 2013  

Received 19 April 2013
Accepted 24 April 2013
Online 27 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.052
wR = 0.164
Data-to-parameter ratio = 21.6
Details
Open access

(1S,2S,5S)-2-Methyl-3-oxo-5-(prop-1-en-2-yl)cyclohexane-1-carbonitrile

aDepartamento de Química Orgánica, Facultade de Química, Universidade de Vigo, E-36310 Vigo, Spain, and bDepartamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Correspondence e-mail: mariacmatos@gmail.com

The molecule of the title compound, C11H15NO, contains a cyclohexanone ring, three defined stereocenters and an exocyclic double bond. The crystal structure is the result of a study on the Michael addition reaction of (S)-carvone with sodium cyanide using ionic liquids as the reaction medium and so the absolute configuration is known from the chemistry. The six-membered ring is in a chair conformation.

Related literature

For recent review of Ionic liquids as solvents, see: Welton (1999[Welton, T. (1999). Chem. Rev. 99, 2071-2084.]); Wasserscheid & Keim (2000[Wasserscheid, P. & Keim, W. (2000). Angew. Chem. Int. Ed. 39., 3772-3789.]).

[Scheme 1]

Experimental

Crystal data
  • C11H15NO

  • Mr = 177.24

  • Orthorhombic, P 21 21 21

  • a = 5.2892 (8) Å

  • b = 10.7213 (16) Å

  • c = 19.559 (3) Å

  • V = 1109.1 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.60 × 0.56 × 0.42 mm

Data collection
  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1995[Sheldrick, G. M. (1995). SADABS. University of Göttingen, Germany.]) Tmin = 0.861, Tmax = 1.000

  • 7138 measured reflections

  • 2590 independent reflections

  • 2112 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.164

  • S = 1.04

  • 2590 reflections

  • 120 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART 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: SHELXTL (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2087 ).


Acknowledgements

This work was supported financially by the Xunta de Galicia (No. EXPTE. CN 2012/184). The work of the MS and Single-crystal X-ray Diffraction divisions of the research support service of the University of Vigo (CACTI) is also gratefully acknowledged. MG thanks the University of Vigo for a PhD fellowship.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1995). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Wasserscheid, P. & Keim, W. (2000). Angew. Chem. Int. Ed. 39., 3772-3789.
Welton, T. (1999). Chem. Rev. 99, 2071-2084.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o799  [ doi:10.1107/S1600536813011197 ]

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