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

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

doi:10.1107/S160053681205009X

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 (C-C) = 0.003 Å
R = 0.046
wR = 0.130
Data-to-parameter ratio = 15.1
Details

14-Ethoxy-4,6-dimethyl-9-phenyl-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, 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-HO hydrogen bonds, forming dimers. These dimers are linked via a third C-HO 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); Hossain et al. (1996); Goel et al. (1997); Su et al. (2009); Xu et al. (2006). For anti-filarial activity studies, see: Casley-Smith et al. (1993). For their enzyme inhibitory activity, see: Pavao et al. (2002). For asymmetry parameters, see: Nardelli (1983).

Experimental

Crystal data

C₂₃H₂₀N₂O₆
M_r = 420.41
Monoclinic, P 2₁ /c
a = 16.8362 (9) Å
b = 8.1692 (4) Å
c = 14.4400 (8) Å
= 98.000 (3)°
V = 1966.72 (18) 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
19858 measured reflections
4247 independent reflections
2943 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.130
S = 1.04
4247 reflections
281 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4O1ⁱ	0.93	2.59	3.514 (3)	172
C5-H5O3ⁱ	0.93	2.45	3.361 (3)	165
C18-H18O6ⁱⁱ	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); 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: SU2537 ).

Acknowledgements

SA thanks the UGC, India, for financial support

References

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