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

G Jagadeesan; S Jayashree; D Kannan; M Bakthadoss; S Aravindhan

doi:10.1107/S1600536813017789

. 2013 Jul 3;69(Pt 8):o1199–o1200. doi: 10.1107/S1600536813017789

14-Methoxy-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, S Jayashree ^b, D Kannan ^c, M Bakthadoss ^c, S Aravindhan ^a,^*

PMCID: PMC3793711 PMID: 24109298

Abstract

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 ▶); Hossain et al. (1996 ▶); Goel et al. (1997 ▶); Su et al. (2009 ▶); Xu et al. (2006 ▶). For anti-filarial activity studies of pyranocoumarin compounds, see: Casley-Smith et al. (1993 ▶) and for enzyme inhibitory activity of pyranocoumarin compounds, see: Pavao et al. (2002 ▶). For a related structure, see: Jagadeesan et al. (2013 ▶). graphic file with name e-69-o1199-scheme1.jpg

Experimental

Crystal data

C₂₃H₂₀N₂O₆
M _r = 420.41
Triclinic,
a = 9.2283 (7) Å
b = 14.0584 (10) Å
c = 16.4457 (13) Å
α = 94.869 (2)°
β = 102.547 (2)°
γ = 105.270 (2)°
V = 1986.1 (3) 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
36657 measured reflections
7558 independent reflections
5648 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.141
S = 1.06
7558 reflections
588 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017789/bt6915sup1.cif

e-69-o1199-sup1.cif^{(46.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017789/bt6915Isup2.hkl

e-69-o1199-Isup2.hkl^{(362.3KB, hkl)}

Click here for additional data file.^{(8.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813017789/bt6915Isup3.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
C21A—H21A⋯O5B ⁱ	0.93	2.55	3.435 (4)	159
C20B—H20B⋯O5A ⁱⁱ	0.93	2.34	3.175 (3)	149
C23B—H23D⋯O6B ⁱⁱⁱ	0.96	2.46	3.249 (4)	139

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

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.

We have already reported a similar compound (Jagadeesan et al., 2013). The title compound crystallizes with two molecules in the asymmetric unit. Geometrical parameters are almost similar the title compound and the previously reported structure. The six-membered pyrone and pyran rings adopt a sofa conformation. The dihedral angle between the mean planes of the pyran and phenyl rings is 66.6 (1) ° and 61.9 (1) ° for the molecule A and B respectively. The crystal packing is stabilized by C—H···O intermolecular hydrogen bonds (Fig. 2 and Table 1).

Experimental

A mixture of 2-ethoxy-6-formylphenyl (2E)-but-2-enoate (0.234 g, 1 mmol) and N,N-dimethylbarbituric acid (0.156 g, 1 mmol) was placed in a round bottom flask and melted at 180 °C for 1 h. After completion of the reaction as indicated by TLC, the crude product was washed with 5 ml of ethylacetate and hexane mixture (1:49 ratio) which successfully provided the pure product in 90% yield as colorless solid. Diffraction quality crystals were obtained by slow evaporation of a solution in (Methonal and ethanol)6:4 ratio.