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Volume 69 
Part 2 
Page o180  
February 2013  

Received 16 December 2012
Accepted 22 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.125
Data-to-parameter ratio = 17.9
Details
Open access

Methyl 6-ethoxy-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carboxylate

aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and bDepartment of Organic Chemistry, University of Madras, Chennai 600 025, India
Correspondence e-mail: aravindhanpresidency@gmail.com

In the title compound, C20H19NO5, the dihedral angle between the mean plane of the pyran ring (which has a half-chair conformation) and the benzene ring of the chromeno ring system is 7.21 (7)°. The dihedral angle between the mean plane of the chromeno ring system and the isoxazole ring is 21.78 (6)°, while the isoxazole ring forms a dihedral angle of 72.60 (8)° with the attached phenyl ring. In the crystal, molecules are linked via pairs of C-H...O hydrogen bonds, forming inversion dimers with an R22(10) ring motif. These dimers are linked via C-H...N hydrogen bonds, forming chains along [001].

Related literature

For the biological activity of chromenopyrroles, see: Caine (1993[Caine, B. (1993). Science, 260, 1814-1816.]), and of benzopyran and isoxazolidine derivatives, see: Lin et al. (1996[Lin, G. N., Lu, C. M., Lin, H. C., Fang, S. C., Shieh, B. J., Hsu, M. F., Wang, J. P., Ko, F. N. & Teng, C. M. (1996). J. Nat. Prod. 59, 834-838.]); Hu et al. (2004[Hu, H., Harrison, T. J. & Wilson, P. D. (2004). J. Org. Chem. 69, 3782-3786.]). For uses of isoxazole derivatives, see: Baraldi et al. (1987[Baraldi, P. G., Barco, A., Benetti, S., Pollini, G. P. & Simoni, D. (1987). Synthesis, pp. 857-869.]); 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.]). For related structures, see: Gangadharan et al. (2011[Gangadharan, R., SethuSankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o942.]); Swaminathan et al. (2011[Swaminathan, K., Sethusankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o905.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C20H19NO5

  • Mr = 353.36

  • Monoclinic, P 21 /c

  • a = 12.9342 (6) Å

  • b = 7.5591 (2) Å

  • c = 18.7138 (8) Å

  • [beta] = 105.440 (2)°

  • V = 1763.63 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 298 K

  • 0.25 × 0.20 × 0.10 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.990

  • 13064 measured reflections

  • 4245 independent reflections

  • 3253 reflections with I > 2[sigma](I)

  • Rint = 0.017

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

  • wR(F2) = 0.125

  • S = 1.03

  • 4245 reflections

  • 237 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6A...O4i 0.97 2.55 3.3875 (19) 145
C8-H8...N1ii 0.98 2.52 3.4269 (19) 154
Symmetry codes: (i) -x, -y+2, -z+2; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

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 (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: SU2543 ).


Acknowledgements

GS and SA thank the UGC, India, for financial support and GS thanks the SAIF, IIT-Madras, for the instrumentation facility.

References

Baraldi, P. G., Barco, A., Benetti, S., Pollini, G. P. & Simoni, D. (1987). Synthesis, pp. 857-869.  [CrossRef]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Caine, B. (1993). Science, 260, 1814-1816.  [CrossRef] [ChemPort] [PubMed] [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]
Gangadharan, R., SethuSankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o942.  [CSD] [CrossRef] [details]
Hu, H., Harrison, T. J. & Wilson, P. D. (2004). J. Org. Chem. 69, 3782-3786.  [CrossRef] [PubMed] [ChemPort]
Lin, G. N., Lu, C. M., Lin, H. C., Fang, S. C., Shieh, B. J., Hsu, M. F., Wang, J. P., Ko, F. N. & Teng, C. M. (1996). J. Nat. Prod. 59, 834-838.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Swaminathan, K., Sethusankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o905.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o180  [ doi:10.1107/S1600536812051720 ]

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