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Volume 69 
Part 1 
Page o80  
January 2013  

Received 3 December 2012
Accepted 7 December 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.130
Data-to-parameter ratio = 15.1
Details
Open access

14-Ethoxy-4,6-dimethyl-9-phenyl-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, C23H20N2O6, the fused pyrone and pyran rings each adopt a sofa conformation. The dihedral angle between the mean planes of the pyran and phenyl rings is 61.9 (1)°. In the crystal, molecules are linked by two pairs of C-H...O hydrogen bonds, forming dimers. These dimers are linked via a third C-H...O hydrogen bond, forming a two-dimensional network parallel to (10-2).

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.]); Hossain et al. (1996[Hossain, C. F., Okuyama, E. & Yamazaki, M. (1996). Chem. Pharm. Bull. (Tokyo), 44, 1535-1539.]); 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.]); Xu et al. (2006[Xu, Z. Q., Pupek, K., Suling, W. J., Enache, L. & Flavin, M. T. (2006). Bioorg. Med. Chem. 14, 4610-4626.]). For anti-filarial activity studies, see: Casley-Smith et al. (1993[Casley-Smith, J. R., Wang, C. T., Casley-Smith, J. R. & Zi-hai, C. (1993). Br. Med. J. 307, 1037-1041.]). For their enzyme inhibitory activity, see: Pavao et al. (2002[Pavao, F., Castilho, M. S., Pupo, M. T., Dias, R. L. A., Correa, A. G., Fernandes, J. B., Da Silva, M. F. G. F., Mafezoli, J., Vieir, P. C. & Oliva, G. (2002). FEBS Lett. 520, 13-17.]). For asymmetry parameters, see: Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C23H20N2O6

  • Mr = 420.41

  • Monoclinic, P 21 /c

  • a = 16.8362 (9) Å

  • b = 8.1692 (4) Å

  • c = 14.4400 (8) Å

  • [beta] = 98.000 (3)°

  • V = 1966.72 (18) 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

  • 19858 measured reflections

  • 4247 independent reflections

  • 2943 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.130

  • S = 1.04

  • 4247 reflections

  • 281 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O1i 0.93 2.59 3.514 (3) 172
C5-H5...O3i 0.93 2.45 3.361 (3) 165
C18-H18...O6ii 0.93 2.56 3.215 (3) 128
Symmetry codes: (i) -x, -y+1, -z; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: SU2537 ).


Acknowledgements

SA thanks the UGC, India, for financial support

References

Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Casley-Smith, J. R., Wang, C. T., Casley-Smith, J. R. & Zi-hai, C. (1993). Br. Med. J. 307, 1037-1041.  [ChemPort]
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]
Hossain, C. F., Okuyama, E. & Yamazaki, M. (1996). Chem. Pharm. Bull. (Tokyo), 44, 1535-1539.  [CrossRef] [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]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
Pavao, F., Castilho, M. S., Pupo, M. T., Dias, R. L. A., Correa, A. G., Fernandes, J. B., Da Silva, M. F. G. F., Mafezoli, J., Vieir, P. C. & Oliva, G. (2002). FEBS Lett. 520, 13-17.  [ISI] [PubMed] [ChemPort]
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]
Xu, Z. Q., Pupek, K., Suling, W. J., Enache, L. & Flavin, M. T. (2006). Bioorg. Med. Chem. 14, 4610-4626.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o80  [ doi:10.1107/S160053681205009X ]

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