3-(2-Methyl­phen­yl)-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbo­nitrile

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

doi:10.1107/S1600536812051732

Volume 69
Part 2
Page o181
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) = 0.008 Å
R = 0.059
wR = 0.146
Data-to-parameter ratio = 8.8
Details

3-(2-Methylphenyl)-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbonitrile

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, C₁₈H₁₄N₂O₂, the pyran ring of the chromeno ring system has a half-chair conformation, and the dihedral angle between its mean plane and the benzene ring is 5.3 (2)°. The isoxazole ring forms a dihedral angle of 74.6 (2)° with the attached benzene ring and is inclined to the mean plane of the chromeno ring system by 15.06 (19)°. In the crystal, there are no significant intermolecular interactions.

Related literature

For the biological importance of 4H-chromene derivatives, see: Cai (2007, 2008); Cai et al. (2006); Gabor (1988); Brooks (1998); Valenti et al. (1993); Hyana & Saimoto (1987); Tang et al. (2007). For related structures, see: Gangadharan et al. (2011); Swaminathan et al. (2011).

Experimental

Crystal data

C₁₈H₁₄N₂O₂
M_r = 290.31
Orthorhombic, P c a 2₁
a = 19.326 (3) Å
b = 10.7866 (17) Å
c = 6.9072 (11) Å
V = 1439.9 (4) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.35 × 0.25 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.970, T_max = 0.987
4742 measured reflections
1750 independent reflections
1100 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.146
S = 1.09
1750 reflections
200 parameters
1 restraint
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.17 e Å^-3

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: SU2544 ).

Acknowledgements

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

References

Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79-101.
Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.
Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.
Gangadharan, R., SethuSankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o942.
Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768.
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.
Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.
Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.

organic compounds