1-Methyl-3-(2-methyl­phen­yl)-3,3a,4,9b-tetra­hydro-1H-chromeno[4,3-c][1,2]oxazole-3a-carbonitrile

Swaminathan, K.; Sethusankar, K.; Murugan, G.; Bakthadoss, M.

doi:10.1107/S1600536811009378

Volume 67
Part 4
Page o905
April 2011

Received 7 March 2011
Accepted 11 March 2011
Online 19 March 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.051
wR = 0.148
Data-to-parameter ratio = 28.3
Details

1-Methyl-3-(2-methylphenyl)-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c][1,2]oxazole-3a-carbonitrile

K. Swaminathan,^a K. Sethusankar,^a ^* G. Murugan ^b and M. Bakthadoss ^b

^aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C₁₉H₁₈N₂O₂, the five-membered isoxazole ring adopts an envelope conformation and the deviation of the N atom from the mean plane of the isoxazole ring is -0.3256 (11) Å. The pyran ring adopts a half-chair conformation. The isoxazole ring forms dihedral angles of 44.07 (7) and 84.23 (7)° with the pyran and methylbenzene rings, respectively. The molecular structure is stabilized by weak C-H [pi] interactions.

Related literature

For the synthesis of the title compound, see: Bakthadoss & Murugan (2010). For the biological and pharmacological activities of isoxazole derivatives, see: Hu et al. (2004); Lin et al. (1996); Rozman et al. (2002). For a related structure, see: Swaminathan et al. (2011). For puckering amplitudes, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₉H₁₈N₂O₂
M_r = 306.35
Monoclinic, P 2₁ /n
a = 11.0120 (4) Å
b = 13.0368 (4) Å
c = 11.1977 (3) Å
= 97.836 (2)°
V = 1592.54 (9) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
23069 measured reflections
5936 independent reflections
3084 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.148
S = 1.01
5936 reflections
210 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11-C16 phenyl ring.

D-HA	D-H	HA	DA	D-HA
C18-H18BCg1ⁱ	0.96	2.99	3.6831 (16)	130
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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, 1997); 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: PV2397 ).

Acknowledgements

K. Swaminathan and K. Sethusankar thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection.

References

Bakthadoss, M. & Murugan, G. (2010). Eur. J. Org. Chem. pp. 5825-5830.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Hu, H., Harrison, T. J. & Wilson, P. D. (2004). J. Org. Chem. 69, 3782-3786.
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.
Rozman, B., Praprotnik, S., Logar, D., Tomsic, M., Hojnik, M., Kos-Golja, M., Accetto, R. & Dolenc, P. (2002). Ann. Rheum. Dis. 61, 567-569.
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, o799.