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Volume 69 
Part 11 
Page o1638  
November 2013  

Received 1 October 2013
Accepted 8 October 2013
Online 16 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.073
wR = 0.214
Data-to-parameter ratio = 15.8
Details
Open access

4-Di­chloro­methyl-4-methyl-5-(nitro­meth­yl)cyclo­hex-2-enone

aVinca Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, PO Box 522, University of Belgrade, 11001 Belgrade, Serbia,bFaculty of Sciences, University of Novi Sad, Trg Dositeja Obradovica 3, 21000 Novi Sad, Serbia,cFaculty of Metallurgy and Technology, University of Montenegro, Cetinjski put bb, 81000 Podgorica, Montenegro, and dFaculty of Sciences, Department of Chemistry, University of Kragujevac, R. Domanovica 12, 34000 Kragujevac, Serbia
Correspondence e-mail: zeljkoj@ac.me

In the title compound, C9H11Cl2NO3, the six-membered ring adopts a screw-chair conformation. In the crystal, two different C-H...O hydrogen bonds involving the same acceptor atom connect the mol­ecules into a chain extending along the c-axis direction.

Related literature

For the synthetic procedure, see: Wenkert et al. (1969[Wenkert, E., Haviv, F. & Zeitlin, A. (1969). J. Am. Chem. Soc. 91, 2299-2307.]). For polyfunctionalized products obtained by similar Michael reactions with carbanions, see: Stefanovic et al. (1983[Stefanovic, M., Jeremic, D., Solujic, S. & Sukdolak, S. (1983). J. Serb. Chem. Soc. 48, 645-653.]); Solujic et al. (1991[Solujic, S., Sukdolak, S. & Ratkovic, Z. (1991). Tetrahedron Lett. 32, 4577-4578.], 1999[Solujic, S., Sukdolak, S. & Krstic, L. J. (1999). Indian J. Chem. Sect. B, 38, 160-165.]). For a related crystal structure, see: Yang & Carter (2010[Yang, H. & Carter, R. G. (2010). Org. Lett. 12, 3108-3111.]).

[Scheme 1]

Experimental

Crystal data
  • C9H11Cl2NO3

  • Mr = 252.09

  • Monoclinic, P 21 /c

  • a = 13.8922 (7) Å

  • b = 10.4531 (9) Å

  • c = 7.8696 (5) Å

  • [beta] = 101.682 (6)°

  • V = 1119.12 (13) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 5.14 mm-1

  • T = 293 K

  • 0.11 × 0.10 × 0.05 mm

Data collection
  • Agilent Gemini S diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.288, Tmax = 1.000

  • 4083 measured reflections

  • 2160 independent reflections

  • 1674 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.073

  • wR(F2) = 0.214

  • S = 1.13

  • 2160 reflections

  • 137 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8...O3i 0.98 2.24 3.189 (5) 164
C1-H1a...O3i 0.97 2.56 3.503 (6) 164
Symmetry code: (i) x, y, z-1.

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.]) 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6936 ).


Acknowledgements

This work was supported by the Ministry of Education, Science and Technological Development of the Republic of Serbia (project Nos. 172014, 172035 and 172034).

References

Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [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]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Solujic, S., Sukdolak, S. & Krstic, L. J. (1999). Indian J. Chem. Sect. B, 38, 160-165.
Solujic, S., Sukdolak, S. & Ratkovic, Z. (1991). Tetrahedron Lett. 32, 4577-4578.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Stefanovic, M., Jeremic, D., Solujic, S. & Sukdolak, S. (1983). J. Serb. Chem. Soc. 48, 645-653.
Wenkert, E., Haviv, F. & Zeitlin, A. (1969). J. Am. Chem. Soc. 91, 2299-2307.  [CrossRef] [ChemPort] [Web of Science]
Yang, H. & Carter, R. G. (2010). Org. Lett. 12, 3108-3111.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1638  [ doi:10.1107/S1600536813027517 ]

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