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Volume 69 
Part 3 
Page o449  
March 2013  

Received 8 November 2012
Accepted 18 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma]() = 0.000 Å
Disorder in main residue
R = 0.080
wR = 0.242
Data-to-parameter ratio = 9.4
Details
Open access

N-[(1E)-5-(3-Chlorophenyl)-3-methylcyclohex-2-en-1-ylidene]hydroxylamine

aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India,bDepartment of Chemistry, Saveetha Engineering College, Chennai, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
Correspondence e-mail: a_sp59@yahoo.in

The whole of the title molecule, C13H14ClNO, is disordered over two sets of sites with a refined occupancy ratio of 0.560 (6):0.440 (6). The oxime group having a C=N double bond adopts an E conformation. The dihedral angles between the rings (all atoms) are 89.5 (5) (major componenent) and 88.0 (6)° (minor component).

Related literature

For applications of oximes, see: Kukushkin et al. (1996[Kukushkin, V. Yu., Tudela, D. & Pombeiro, A. J. L. (1996). Coord. Chem. Rev. 156, 333-362.]): Chaudhuri (2003[Chaudhuri, P. (2003). Coord. Chem. Rev. 243, 143-168.]). For a related structure of a chlorophenyl oxime derivative, see: Ravichandran et al. (2010[Ravichandran, K., Ramesh, P., Rani, M., Kabilan, S. & Ponnuswamy, M. N. (2010). Acta Cryst. E66, o1506.]).

[Scheme 1]

Experimental

Crystal data
  • C13H14ClNO

  • Mr = 235.70

  • Tetragonal, I 41 /a

  • a = 19.7898 (8) Å

  • c = 12.4416 (11) Å

  • V = 4872.6 (5) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 295 K

  • 0.25 × 0.22 × 0.19 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.930, Tmax = 0.946

  • 19841 measured reflections

  • 2394 independent reflections

  • 1765 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.080

  • wR(F2) = 0.242

  • S = 1.05

  • 2394 reflections

  • 255 parameters

  • 93 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.72 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 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: 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: NK2191 ).


Acknowledgements

The authors thank Dr Babu Varghese and the SAIF, IIT, Chennai, India, for the data collection.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chaudhuri, P. (2003). Coord. Chem. Rev. 243, 143-168.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kukushkin, V. Yu., Tudela, D. & Pombeiro, A. J. L. (1996). Coord. Chem. Rev. 156, 333-362.  [CrossRef] [ChemPort] [ISI]
Ravichandran, K., Ramesh, P., Rani, M., Kabilan, S. & Ponnuswamy, M. N. (2010). Acta Cryst. E66, o1506.  [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o449  [ doi:10.1107/S1600536813004698 ]

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