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Volume 69 
Part 5 
Page o716  
May 2013  

Received 18 March 2013
Accepted 9 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.132
Data-to-parameter ratio = 17.8
Details
Open access

rac-3-(4-Chlorophenyl)-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbonitrile

aPost Graduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: seshadri_pr@yahoo.com

The title compound, C17H11ClN2O2, which contains two stereogenic C atoms, crystallizes in a centrosymmetric space group as a racemate. The pyran ring and the isoxazole ring adopt sofa and twisted conformations, respectively. The dihedral angle between the benzene ring and the mean plane through the near coplanar atoms of the pyran ring is 4.17 (5)°. The molecular conformation features a weak C-H...O contact. In the crystal, C-H...O hydrogen bonds link the molecules, forming chains along the a-axis direction.

Related literature

For the biological activity of isoxazole derivatives, see: Mullen et al. (1988[Mullen, G. B., DeCory, T. R., Mitchell, J. T., Allen, S. D., Kinsolving, C. R. & Georgiev, V. S. (1988). J. Med. Chem. 31, 2008-2014.]); Eddington et al. (2002[Eddington, N. D., Cox, D. S., Roberts, R. R., Butcher, R. J., Edafiogho, I. O., Stables, J. P., Cooke, N., Goodwin, A. M., Smith, C. A. & Scott, K. R. (2002). Eur. J. Med. Chem. 37, 635-648.]); Kashiwada et al. (2001[Kashiwada, Y., Yamazaki, K., Ikeshiro, Y., Yamagishi, T., Fujioka, T., Mihashi, K., Mizuki, K., Cosentino, L. M., Fowke, K., Natschke, S. L. M. & Lee, K. H. (2001). Tetrahedron, 57, 1559-1563.]); Caine (1993[Caine, B. (1993). Science, 260, 1814-1816.]). For a related structure, see: Paramasivam et al. (2012[Paramasivam, S., Srinivasan, J., Seshadri, P. R. & Bakthadoss, M. (2012). Acta Cryst. E68, o1660.]). For conformational analysis and pukering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H11ClN2O2

  • Mr = 310.73

  • Monoclinic, P 21 /c

  • a = 6.7891 (2) Å

  • b = 13.9921 (3) Å

  • c = 15.1788 (3) Å

  • [beta] = 101.175 (1)°

  • V = 1414.55 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 298 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 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.]) Tmin = 0.921, Tmax = 0.946

  • 13620 measured reflections

  • 3541 independent reflections

  • 2865 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.132

  • S = 1.00

  • 3541 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13-H13...O1 0.93 2.42 2.7733 (19) 102
C5-H5...O2i 0.93 2.47 3.3422 (19) 156
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., 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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2448 ).


Acknowledgements

The authors acknowledge the Technology Business Incubator (TBI), CAS in Crystallography, University of Madras, Chennai 600 025, India, for the data collection.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.
Caine, B. (1993). Science, 260, 1814-1816.  [CrossRef] [ChemPort] [PubMed] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Eddington, N. D., Cox, D. S., Roberts, R. R., Butcher, R. J., Edafiogho, I. O., Stables, J. P., Cooke, N., Goodwin, A. M., Smith, C. A. & Scott, K. R. (2002). Eur. J. Med. Chem. 37, 635-648.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kashiwada, Y., Yamazaki, K., Ikeshiro, Y., Yamagishi, T., Fujioka, T., Mihashi, K., Mizuki, K., Cosentino, L. M., Fowke, K., Natschke, S. L. M. & Lee, K. H. (2001). Tetrahedron, 57, 1559-1563.  [ISI] [CSD] [CrossRef] [ChemPort]
Mullen, G. B., DeCory, T. R., Mitchell, J. T., Allen, S. D., Kinsolving, C. R. & Georgiev, V. S. (1988). J. Med. Chem. 31, 2008-2014.  [CrossRef] [ChemPort] [PubMed] [ISI]
Paramasivam, S., Srinivasan, J., Seshadri, P. R. & Bakthadoss, M. (2012). Acta Cryst. E68, o1660.  [CSD] [CrossRef] [details]
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]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o716  [ doi:10.1107/S1600536813009653 ]

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