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Volume 69 
Part 7 
Page o1121  
July 2013  

Received 1 June 2013
Accepted 11 June 2013
Online 19 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.130
Data-to-parameter ratio = 21.5
Details
Open access

3-[(E)-2-(4-Chlorophenyl)ethenyl]-5,5-dimethylcyclohex-2-en-1-one

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, Tamilnadu, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C16H17ClO, the cyclohexene ring adopts a half-chair conformation and the best plane through the six ring atoms makes a dihedral angle of 6.69 (7)° with the chlorophenyl ring. In the crystal, pairs of C-H...O hydrogen bonds link the molecules into centrosymmetric R22(20) dimers. The dimers are linked into an infinite chains along the b-axis direction by further C-H...O hydrogen bonds.

Related literature

For the pharmacological activity of cyclohexanone derivatives, see: Puetz et al.(2003[Puetz, C., Buschmann, H. & Koegel, B. (2003). US Patent Appl. No. 20030096811.]); Rajveer et al. (2010[Rajveer, Ch., Stephenrathinaraj, B., Sudharshini, S., Kumaraswamy, D., Shreshtha, B. & Choudhury, P. K. (2010). Res. J. Pharm. Biol. Chem. Sci. 1, 99-107.]). For a related structure, see: Hema et al. (2006[Hema, R., Parthasarathi, V., Ravikumar, K., Pandiarajan, K. & Murugavel, K. (2006). Acta Cryst. E62, o703-o705.]). For conformational analysis, see: Allinger (1977[Allinger, N. L. (1977). J. Am. Chem. Soc. 99, 8127-8134.]); Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C16H17ClO

  • Mr = 260.75

  • Monoclinic, P 21 /n

  • a = 13.7630 (4) Å

  • b = 6.0841 (2) Å

  • c = 17.5003 (6) Å

  • [beta] = 105.726 (2)°

  • V = 1410.54 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.927, Tmax = 0.951

  • 13158 measured reflections

  • 3552 independent reflections

  • 2611 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.130

  • S = 1.03

  • 3552 reflections

  • 165 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O1i 0.93 2.41 3.301 (2) 159
C14-H14B...O1ii 0.97 2.57 3.4299 (18) 148
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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.]); software used to prepare material for publication: SHELXL97 and 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: BT6912 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and ZF thanks the UGC for a meritorious fellowship.

References

Allinger, N. L. (1977). J. Am. Chem. Soc. 99, 8127-8134.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
Hema, R., Parthasarathi, V., Ravikumar, K., Pandiarajan, K. & Murugavel, K. (2006). Acta Cryst. E62, o703-o705.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Puetz, C., Buschmann, H. & Koegel, B. (2003). US Patent Appl. No. 20030096811.
Rajveer, Ch., Stephenrathinaraj, B., Sudharshini, S., Kumaraswamy, D., Shreshtha, B. & Choudhury, P. K. (2010). Res. J. Pharm. Biol. Chem. Sci. 1, 99-107.  [ChemPort]
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, o1121  [ doi:10.1107/S1600536813016255 ]

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