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

G Jagadeesan; D Kannan; M Bakthadoss; S Aravindhan

doi:10.1107/S160053681205009X

. 2012 Dec 12;69(Pt 1):o80. doi: 10.1107/S160053681205009X

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, S Aravindhan ^a,^*

PMCID: PMC3588261 PMID: 23476462

Abstract

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 ▶); 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,
a = 16.8362 (9) Å
b = 8.1692 (4) Å
c = 14.4400 (8) Å
β = 98.000 (3)°
V = 1966.72 (18) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.130
S = 1.04
4247 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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 Material

Click here for additional data file.^{(19.7KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681205009X/su2537sup1.cif

e-69-00o80-sup1.cif^{(19.7KB, cif)}

Click here for additional data file.^{(203.9KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681205009X/su2537Isup2.hkl

e-69-00o80-Isup2.hkl^{(203.9KB, hkl)}

Click here for additional data file.^{(8.4KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681205009X/su2537Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

SA thanks the UGC, India, for financial support

supplementary crystallographic information

Comment

Coumarin derivatives show strong activity against cancer cell lines (Kawaii et al., 2001) and exhibit monoamine oxidase inhibitory activity (Hossain et al., 1996). Antiulcer activity of some naturally occurring pyranocoumarins has been reported (Goel et al., 1997). They also show anti-hepatitis B virus, anti-filarial (Casley-Smith et al., 1993) and cytotoxic activities (Su et al., 2009) and anti-TB activity (Xu et al., 2006). One natural source coumarin derivative, Chalepin, inhibits the glyceraldehyde-3-phosphate dehydrogenase of parasites (Protein Data Bank ID code 1 K3T) (Pavao et al., 2002). Herein, we report on the crystal structure of the title coumarin derivative.

In the title molecule (Fig. 1) the six-membered pyrone ring of the coumarin ring system [DS (C9) = 0.163 (1) Å and D2 (C9—C8) = 0.029 (1) Å] and the pyran ring [DS (C8) = 0.065 (1) Å and D2 (C8—C7) = 0.075 (1) Å] both adopt a sofa conformation defined by the above asymmetry parameters (Nardelli, 1983). The mean plane of the pyran ring and the phenyl ring are tilted with respect to one another with a dihedral angle of 61.9 (1) °. The torsion angles H9—C9—C8—H8 = 51 (2)° and H8—C8—C7—H7 = 175.12 (2)°, define the ring fusions involving the in the fused pyrone and pyran ring system of the coumarin moiety.

In the crystal, molecules are linked by two pairs of C-H···O hydrogen bonds to form dimers. These dimers are linked via a third C-H···O hydrogen bond forming a two-dimensional network parallel to (10-2) [Table 1 and Fig. 2].

Experimental

A mixture of 2-ethoxy-6-formylphenyl (2E)-3-phenylprop-2-enoate (0.296 g, 1 mmol) and N,N-dimethylbarbituric acid (0.156 g, 1 mmol) was placed in a round bottom flask and melted at 453 K for 1 h. After completion of the reaction, as indicated by TLC, the crude product was washed with 5 ml of an ethylacetate and hexane mixture (1:49 ratio) which successfully provided the pure product in 92% yield as a colourless solid. Diffraction quality crystals were obtained by slow evaporation of a solution in ethyl acetate.