14-Eth­oxy-4,6,9-trimethyl-8,12-dioxa-4,6-diaza­tetra­cyclo­[8.8.0.02,7.013,18]octa­deca-2(7),13,15,17-tetra­ene-3,5,11-trione

Jagadeesan, G.; Kannan, D.; Bakthadoss, M.; Aravindhan, S.

doi:10.1107/S1600536813000743

Volume 69
Part 2
Page o272
February 2013

Received 2 December 2012
Accepted 8 January 2013
Online 23 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.049
wR = 0.151
Data-to-parameter ratio = 22.9
Details

14-Ethoxy-4,6,9-trimethyl-8,12-dioxa-4,6-diazatetracyclo[8.8.0.0^2,7.0^13,18]octadeca-2(7),13,15,17-tetraene-3,5,11-trione

G. Jagadeesan,^a D. Kannan,^b M. Bakthadoss ^b and S. Aravindhan ^a ^*

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

In the title compound, C₁₉H₂₀N₂O₆, the pyrone and pyran rings adopt envelope conformations with the same common C atom as the flap, the dihedral angle between the planes of the remaining ring atoms being 68.27 (4)°. The planar atoms of the pyran ring and the diazacyclic ring are almost coplanar, the dihedral angle between their mean planes being 3.29 (7)°. Moreover, the planar atoms of the pyrone ring and benzene ring of the coumarin unit are also close to coplanar, the dihedral angle between their mean planes being 8.03 (9)°. The methoxy group lies in the plane of the benzene ring, with a dihedral angle between their mean planes of 9.4 (2)°. In the crystal, the molecules are linked by C-HO hydrogen bonds resulting in sheets of molecules in the ac plane.

Related literature

For the biological activity of pyranocoumarin compounds, see: Kawaii et al. (2001); Goel et al. (1997); Su et al. (2009). For a related structure, see: Pojarová et al. (2012).

Experimental

Crystal data

C₁₉H₂₀N₂O₆
M_r = 372.37
Monoclinic, P 2₁ /n
a = 9.3526 (3) Å
b = 17.9559 (5) Å
c = 10.9158 (3) Å
= 101.346 (1)°
V = 1797.31 (9) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2004) T_min = 0.979, T_max = 0.983
21571 measured reflections
5615 independent reflections
3743 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.151
S = 1.03
5615 reflections
245 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O6ⁱ	0.98	2.40	3.1480 (17)	132
C18-H18CO3ⁱⁱ	0.96	2.45	3.252 (2)	140
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2613 ).

Acknowledgements

SA thanks the UGC, India, for financial support

References

Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Goel, R. K., Maiti, R. N., Manickam, M. & Ray, A. B. (1997). Indian J. Exp. Biol. 35, 1080-1083.
Kawaii, S., Tomono, Y., Ogawa, K., Sugiura, M., Yano, M., Yoshizawa, Y., Ito, C. & Furukawa, H. (2001). Anticancer Res. 21, 1905-1911.
Pojarová, M., Dusek, M., Sedláková, Z. & Makrlík, E. (2012). Acta Cryst. E68, o805-o806.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Su, C. R., Yeh, S. F., Liu, C. M., Damu, A. G., Kuo, T. H., Chiang, P. C., Bastow, K. F., Lee, K. H. & Wu, T. S. (2009). Bioorg. Med. Chem. 17, 6137-6143.