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Volume 69 
Part 5 
Page o758  
May 2013  

Received 10 April 2013
Accepted 15 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.061
wR = 0.199
Data-to-parameter ratio = 13.9
Details
Open access

3-[(1-Bromonaphthalen-2-yl)methoxy]-5,5-dimethylcyclohex-2-enone

aSchool of Chemistry and Chemical Engineering, Henan Normal University, Henan 453007, People's Republic of China
Correspondence e-mail: xinyingzhang@htu.cn

In the title compound, C19H19BrO2, the cyclohexenone ring adopts an envelope conformation with the C atom bearing the methyl substituents as the flap. In the crystal, weak [pi]-[pi] stacking is observed between parallel aromatic rings of adjacent molecules, the centroid-centroid distance being 3.694 (6) Å. The entire bromonaphthylmethyl unit is disordered over two orientations, with a site-occupancy ratio of 0.5214 (19):0.4786 (19).

Related literature

For the biological activity and applications of cyclohex-2-enone derivatives, see: Aghil et al. (1992[Aghil, O., Bibby, M. C., Carrington, S. J., Douglas, K. T., Phillips, R. M. & Shing, T. K. M. (1992). Anti-Cancer Drug Des. 7, 67-82.]); Correcia et al. (2001[Correcia, S. D., David, J. M., David, J. P., Chai, H. B., Pezzuto, J. M. & Cordell, G. A. (2001). Phytochemistry, 56, 781-784.]); Ghorab et al. (2011[Ghorab, M. M., Al-Said, M. S. & El-Hossary, E. M. (2011). J. Heterocycl. Chem. 48, 563-571.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19BrO2

  • Mr = 359.25

  • Monoclinic, P 21 /c

  • a = 13.986 (3) Å

  • b = 9.9970 (18) Å

  • c = 11.859 (2) Å

  • [beta] = 91.169 (2)°

  • V = 1657.8 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.48 mm-1

  • T = 296 K

  • 0.32 × 0.29 × 0.27 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.504, Tmax = 0.554

  • 11934 measured reflections

  • 3075 independent reflections

  • 1931 reflections with I > 2[sigma](I)

  • Rint = 0.074

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.199

  • S = 1.07

  • 3075 reflections

  • 222 parameters

  • 72 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 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 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5694 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 21172057).

References

Aghil, O., Bibby, M. C., Carrington, S. J., Douglas, K. T., Phillips, R. M. & Shing, T. K. M. (1992). Anti-Cancer Drug Des. 7, 67-82.  [PubMed] [ChemPort]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Correcia, S. D., David, J. M., David, J. P., Chai, H. B., Pezzuto, J. M. & Cordell, G. A. (2001). Phytochemistry, 56, 781-784.  [ISI] [PubMed]
Ghorab, M. M., Al-Said, M. S. & El-Hossary, E. M. (2011). J. Heterocycl. Chem. 48, 563-571.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o758  [ doi:10.1107/S160053681301026X ]

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