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

Suresh, G.; Srinivasan, J.; Bakthadoss, M.; Aravindhan, S.

doi:10.1107/S1600536812051720

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 (C-C) = 0.002 Å
R = 0.042
wR = 0.125
Data-to-parameter ratio = 17.9
Details

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

G. Suresh,^a J. Srinivasan,^b M. Bakthadoss ^b and S. Aravindhan ^a ^*

^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-HO hydrogen bonds, forming inversion dimers with an R²₂(10) ring motif. These dimers are linked via C-HN hydrogen bonds, forming chains along [001].

Related literature

For the biological activity of chromenopyrroles, see: Caine (1993), and of benzopyran and isoxazolidine derivatives, see: Lin et al. (1996); Hu et al. (2004). For uses of isoxazole derivatives, see: Baraldi et al. (1987); Eddington et al. (2002). For related structures, see: Gangadharan et al. (2011); Swaminathan et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₀H₁₉NO₅
M_r = 353.36
Monoclinic, P 2₁ /c
a = 12.9342 (6) Å
b = 7.5591 (2) Å
c = 18.7138 (8) Å
= 105.440 (2)°
V = 1763.63 (12) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.976, T_max = 0.990
13064 measured reflections
4245 independent reflections
3253 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.125
S = 1.03
4245 reflections
237 parameters
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6AO4ⁱ	0.97	2.55	3.3875 (19)	145
C8-H8N1ⁱⁱ	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
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Caine, B. (1993). Science, 260, 1814-1816.
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Hu, H., Harrison, T. J. & Wilson, P. D. (2004). J. Org. Chem. 69, 3782-3786.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Swaminathan, K., Sethusankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o905.

organic compounds