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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 [sigma](C-C) = 0.002 Å
R = 0.049
wR = 0.151
Data-to-parameter ratio = 22.9
Details
Open access

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

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-H...O 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[Kawaii, S., Tomono, Y., Ogawa, K., Sugiura, M., Yano, M., Yoshizawa, Y., Ito, C. & Furukawa, H. (2001). Anticancer Res. 21, 1905-1911.]); Goel et al. (1997[Goel, R. K., Maiti, R. N., Manickam, M. & Ray, A. B. (1997). Indian J. Exp. Biol. 35, 1080-1083.]); Su et al. (2009[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.]). For a related structure, see: Pojarová et al. (2012[Pojarová, M., Dusek, M., Sedláková, Z. & Makrlík, E. (2012). Acta Cryst. E68, o805-o806.]).

[Scheme 1]

Experimental

Crystal data
  • C19H20N2O6

  • Mr = 372.37

  • Monoclinic, P 21 /n

  • a = 9.3526 (3) Å

  • b = 17.9559 (5) Å

  • c = 10.9158 (3) Å

  • [beta] = 101.346 (1)°

  • V = 1797.31 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.983

  • 21571 measured reflections

  • 5615 independent reflections

  • 3743 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.151

  • S = 1.03

  • 5615 reflections

  • 245 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O6i 0.98 2.40 3.1480 (17) 132
C18-H18C...O3ii 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[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: 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: 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.  [ISI] [CrossRef] [ChemPort] [details]
Goel, R. K., Maiti, R. N., Manickam, M. & Ray, A. B. (1997). Indian J. Exp. Biol. 35, 1080-1083.  [ChemPort] [PubMed]
Kawaii, S., Tomono, Y., Ogawa, K., Sugiura, M., Yano, M., Yoshizawa, Y., Ito, C. & Furukawa, H. (2001). Anticancer Res. 21, 1905-1911.  [PubMed] [ChemPort]
Pojarová, M., Dusek, M., Sedláková, Z. & Makrlík, E. (2012). Acta Cryst. E68, o805-o806.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o272  [ doi:10.1107/S1600536813000743 ]

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