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Volume 69 
Part 5 
Page o664  
May 2013  

Received 21 March 2013
Accepted 28 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.112
Data-to-parameter ratio = 15.1
Details
Open access

rac-Methyl 3-(2-methoxyphenyl)-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carboxylate

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, C19H17NO5, comprising two stereogenic C atoms of the same configuration, crystallizes in a centrosymmetric space group as a racemate. The pyran ring adopts a half-chair conformation, while the isoxazole ring adopts an envelope conformation with the C atom bonded to the methoxyphenyl group as the flap. The dihedral angle between the mean plane of the pyran ring and the adjacent benzene ring is 5.86 (5)°. In the crystal, molecules are linked by a weak C-H...O hydrogen bond, forming a chain along the a axis.

Related literature

For the biological activity of isoxazole and benzpyran derivatives, see: Winn et al. (1976[Winn, M., Arendsen, D., Dodge, P., Dren, A., Dunnigan, D., Hallas, R., Hwang, K., Kyncl, J., Lee, Y. H., Plotnikoff, N., Young Zaugg, H., Dalzell, H. & Razdan, R. K. (1976). J. Med. Chem. 19, 461-471.]); Rozman et al. (2002[Rozman, B., Praprotnik, S., Logar, D., Tomsic, M., Hojnik, M., Kos-Golja, M., Accetto, R. & Dolenc, P. (2002). Ann. Rheum. Dis. 61, 567-569.]); Caine (1993[Caine, B. (1993). Science, 260, 1814-1816.]). For conformational analysis and puckering parameters, see: Cremer & Pople, (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For a related structure, see: Paramasivam et al. (2012[Paramasivam, S., Srinivasan, J., Seshadri, P. R. & Bakthadoss, M. (2012). Acta Cryst. E68, o1987.]).

[Scheme 1]

Experimental

Crystal data
  • C19H17NO5

  • Mr = 339.34

  • Triclinic, [P \overline 1]

  • a = 9.4804 (4) Å

  • b = 9.6401 (4) Å

  • c = 10.7013 (5) Å

  • [alpha] = 81.308 (2)°

  • [beta] = 67.801 (2)°

  • [gamma] = 69.085 (2)°

  • V = 845.71 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 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, SAINT and SADABS. Bruker AXS Ins., Madison, Wisconsin, USA.]) Tmin = 0.971, Tmax = 0.981

  • 12631 measured reflections

  • 3462 independent reflections

  • 3012 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.112

  • S = 1.04

  • 3462 reflections

  • 229 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C17-H17...O3i 0.93 2.42 3.3084 (19) 159
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Ins., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: IS5259 ).


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, SAINT and SADABS. 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]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Paramasivam, S., Srinivasan, J., Seshadri, P. R. & Bakthadoss, M. (2012). Acta Cryst. E68, o1987.  [CSD] [CrossRef] [details]
Rozman, B., Praprotnik, S., Logar, D., Tomsic, M., Hojnik, M., Kos-Golja, M., Accetto, R. & Dolenc, P. (2002). Ann. Rheum. Dis. 61, 567-569.  [ISI] [CrossRef] [PubMed] [ChemPort]
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]
Winn, M., Arendsen, D., Dodge, P., Dren, A., Dunnigan, D., Hallas, R., Hwang, K., Kyncl, J., Lee, Y. H., Plotnikoff, N., Young Zaugg, H., Dalzell, H. & Razdan, R. K. (1976). J. Med. Chem. 19, 461-471.  [CrossRef] [ChemPort] [PubMed] [ISI]


Acta Cryst (2013). E69, o664  [ doi:10.1107/S1600536813008635 ]

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