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Volume 69 
Part 8 
Pages o1199-o1200  
August 2013  

Received 12 June 2013
Accepted 28 June 2013
Online 3 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.141
Data-to-parameter ratio = 12.9
Details
Open access

14-Methoxy-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,bCenter for Advanced Study in Botany, University of Madras, Guindy Campus, Chennai 600 025, India, and cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: aravindhanpresidency@gmail.com

The title compound, C23H20N2O6, crystallizes with two molecules in the asymmetric unit in which the dihedral angles between the mean planes of the pyran and phenyl rings are 66.6 (1) and 61.9 (1) °. The fused pyrone and pyran rings each adopts a sofa conformation. In the crystal, C-H...O hydrogen bonds link the molecules, forming a two-dimensional network parallel to [001].

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 of pyranocoumarin compounds, 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.]) and for enzyme inhibitory activity of pyranocoumarin compounds, 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 a related structure, see: Jagadeesan et al. (2013[Jagadeesan, G., Kannan, D., Bakthadoss, M. & Aravindhan, S. (2013). Acta Cryst. E69, o80.]).

[Scheme 1]

Experimental

Crystal data
  • C23H20N2O6

  • Mr = 420.41

  • Triclinic, [P \overline 1]

  • a = 9.2283 (7) Å

  • b = 14.0584 (10) Å

  • c = 16.4457 (13) Å

  • [alpha] = 94.869 (2)°

  • [beta] = 102.547 (2)°

  • [gamma] = 105.270 (2)°

  • V = 1986.1 (3) 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

  • 36657 measured reflections

  • 7558 independent reflections

  • 5648 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.141

  • S = 1.06

  • 7558 reflections

  • 588 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C21A-H21A...O5Bi 0.93 2.55 3.435 (4) 159
C20B-H20B...O5Aii 0.93 2.34 3.175 (3) 149
C23B-H23D...O6Biii 0.96 2.46 3.249 (4) 139
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+2, -y+2, -z+1; (iii) x, y-1, z.

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: BT6915 ).


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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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]
Jagadeesan, G., Kannan, D., Bakthadoss, M. & Aravindhan, S. (2013). Acta Cryst. E69, o80.  [CSD] [CrossRef] [IUCr Journals]
Kawaii, S., Tomono, Y., Ogawa, K., Sugiura, M., Yano, M., Yoshizawa, Y., Ito, C. & Furukawa, H. (2001). Anticancer Res. 21, 1905-1911.  [PubMed] [ChemPort]
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.  [Web of Science] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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, o1199-o1200   [ doi:10.1107/S1600536813017789 ]

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