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

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o80

https://doi.org/10.1107/S160053681205009X

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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

(Received 3 December 2012; accepted 7 December 2012; online 12 December 2012)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.046
wR(F²) = 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

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); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681205009X/su2537sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681205009X/su2537Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681205009X/su2537Isup3.cml

checkCIF report

Comment top

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].

Related literature top

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 top

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.

Structure description top

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).

Computing details top

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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom lables. Displacement ellipsoids are drawn at the 30% probability level (H atoms have been omitted for clarity).
	Fig. 2. A view along the c axis of the crystal packing of the title compound. The C-H···O hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms not involved in these interactions have been omitted.

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 top

Crystal data top

C₂₃H₂₀N₂O₆	F(000) = 880
M_r = 420.41	D_x = 1.420 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8834 reflections
a = 16.8362 (9) Å	θ = 2.1–31.2°
b = 8.1692 (4) Å	µ = 0.10 mm⁻¹
c = 14.4400 (8) Å	T = 293 K
β = 98.000 (3)°	Block, colourless
V = 1966.72 (18) Å³	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4247 independent reflections
Radiation source: fine-focus sealed tube	2943 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω and φ scan	θ_max = 26.9°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −21→21
T_min = 0.979, T_max = 0.983	k = −10→10
19858 measured reflections	l = −18→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0545P)² + 0.6922P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4247 reflections	Δρ_max = 0.28 e Å⁻³
281 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0027 (7)

Crystal data top

C₂₃H₂₀N₂O₆	V = 1966.72 (18) Å³
M_r = 420.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.8362 (9) Å	µ = 0.10 mm⁻¹
b = 8.1692 (4) Å	T = 293 K
c = 14.4400 (8) Å	0.25 × 0.20 × 0.20 mm
β = 98.000 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4247 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2004)	2943 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.983	R_int = 0.039
19858 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.04	Δρ_max = 0.28 e Å⁻³
4247 reflections	Δρ_min = −0.19 e Å⁻³
281 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O4	0.16385 (8)	0.54434 (17)	0.34721 (9)	0.0456 (4)
O2	0.22837 (7)	0.36035 (17)	0.07300 (9)	0.0438 (3)
O3	0.12638 (8)	0.20829 (18)	0.09730 (10)	0.0513 (4)
O6	0.41821 (8)	0.2943 (2)	0.41399 (10)	0.0548 (4)
O5	0.29499 (10)	0.5286 (2)	0.64093 (10)	0.0632 (4)
N1	0.23397 (10)	0.5455 (2)	0.49074 (11)	0.0433 (4)
O1	0.29820 (9)	0.5214 (2)	−0.04780 (10)	0.0547 (4)
N2	0.35919 (9)	0.4205 (2)	0.52645 (11)	0.0450 (4)
C13	0.36037 (11)	0.3696 (2)	0.43419 (13)	0.0412 (4)
C11	0.23195 (11)	0.4981 (2)	0.39956 (13)	0.0379 (4)
C14	0.32631 (10)	0.4522 (2)	0.20279 (13)	0.0369 (4)
C10	0.29172 (10)	0.4137 (2)	0.36840 (13)	0.0367 (4)
C16	0.33429 (11)	0.5327 (2)	0.04229 (14)	0.0427 (5)
C20	0.17880 (10)	0.2965 (2)	0.13077 (13)	0.0387 (4)
C15	0.29621 (10)	0.4502 (2)	0.10910 (13)	0.0378 (4)
C9	0.28330 (10)	0.3522 (2)	0.26942 (12)	0.0365 (4)
H9	0.3045	0.2404	0.2707	0.044*
C8	0.19371 (10)	0.3446 (2)	0.23246 (13)	0.0378 (4)
H8	0.1691	0.2618	0.2685	0.045*
C7	0.15484 (11)	0.5103 (2)	0.24763 (13)	0.0386 (4)
H7	0.1821	0.5959	0.2164	0.046*
C1	0.06624 (11)	0.5170 (2)	0.21317 (14)	0.0401 (4)
C12	0.29624 (12)	0.4995 (3)	0.55866 (14)	0.0460 (5)
C22	0.16917 (14)	0.6433 (3)	0.52058 (15)	0.0566 (6)
H22A	0.1808	0.6647	0.5864	0.085*
H22C	0.1196	0.5842	0.5079	0.085*
H22B	0.1647	0.7450	0.4870	0.085*
C17	0.40429 (12)	0.6166 (3)	0.07246 (15)	0.0515 (5)
H17	0.4313	0.6705	0.0294	0.062*
C19	0.39570 (11)	0.5407 (3)	0.23118 (15)	0.0478 (5)
H19	0.4163	0.5459	0.2943	0.057*
C18	0.43425 (12)	0.6208 (3)	0.16645 (16)	0.0555 (6)
H18	0.4811	0.6785	0.1863	0.067*
C6	0.04019 (13)	0.5835 (3)	0.12795 (15)	0.0547 (6)
H6	0.0773	0.6274	0.0928	0.066*
C21	0.33837 (15)	0.5946 (3)	−0.11801 (15)	0.0631 (6)
H21A	0.3071	0.5791	−0.1782	0.095*
H21B	0.3900	0.5445	−0.1174	0.095*
H21C	0.3451	0.7096	−0.1056	0.095*
C23	0.42923 (13)	0.3828 (3)	0.59566 (16)	0.0614 (6)
H23A	0.4690	0.3278	0.5654	0.092*
H23B	0.4132	0.3133	0.6434	0.092*
H23C	0.4513	0.4825	0.6234	0.092*
C2	0.01032 (13)	0.4541 (3)	0.26413 (19)	0.0633 (7)
H2	0.0267	0.4096	0.3230	0.076*
C4	−0.09540 (13)	0.5224 (3)	0.14226 (19)	0.0647 (7)
H4	−0.1496	0.5229	0.1181	0.078*
C5	−0.04080 (15)	0.5868 (3)	0.09263 (18)	0.0679 (7)
H5	−0.0575	0.6337	0.0345	0.082*
C3	−0.07031 (14)	0.4565 (3)	0.2283 (2)	0.0738 (8)
H3	−0.1077	0.4129	0.2631	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0445 (7)	0.0561 (8)	0.0357 (7)	0.0139 (6)	0.0034 (6)	−0.0044 (6)
O2	0.0415 (7)	0.0573 (8)	0.0326 (7)	−0.0085 (6)	0.0054 (6)	−0.0022 (6)
O3	0.0488 (8)	0.0552 (8)	0.0481 (9)	−0.0117 (7)	0.0006 (7)	−0.0065 (7)
O6	0.0386 (7)	0.0730 (10)	0.0522 (9)	0.0106 (7)	0.0048 (6)	0.0051 (8)
O5	0.0691 (10)	0.0884 (12)	0.0320 (8)	−0.0072 (9)	0.0067 (7)	−0.0053 (8)
N1	0.0472 (9)	0.0523 (10)	0.0315 (9)	0.0016 (7)	0.0097 (7)	−0.0019 (7)
O1	0.0533 (8)	0.0768 (10)	0.0347 (8)	−0.0044 (7)	0.0084 (6)	0.0080 (7)
N2	0.0401 (9)	0.0587 (10)	0.0347 (9)	−0.0063 (8)	0.0003 (7)	0.0046 (8)
C13	0.0382 (10)	0.0483 (11)	0.0371 (11)	−0.0051 (9)	0.0049 (8)	0.0061 (9)
C11	0.0390 (9)	0.0414 (10)	0.0330 (10)	−0.0023 (8)	0.0034 (8)	0.0026 (8)
C14	0.0316 (9)	0.0449 (10)	0.0352 (10)	0.0033 (8)	0.0079 (7)	−0.0010 (8)
C10	0.0362 (9)	0.0423 (10)	0.0318 (10)	−0.0009 (8)	0.0056 (7)	0.0034 (8)
C16	0.0411 (10)	0.0526 (11)	0.0354 (11)	0.0044 (9)	0.0088 (8)	0.0028 (9)
C20	0.0347 (9)	0.0411 (10)	0.0400 (11)	0.0022 (8)	0.0042 (8)	−0.0019 (8)
C15	0.0325 (9)	0.0444 (10)	0.0371 (11)	0.0014 (8)	0.0071 (8)	−0.0011 (8)
C9	0.0326 (9)	0.0421 (10)	0.0350 (10)	0.0026 (7)	0.0054 (7)	0.0005 (8)
C8	0.0351 (9)	0.0427 (10)	0.0363 (10)	−0.0020 (8)	0.0068 (7)	0.0015 (8)
C7	0.0383 (9)	0.0443 (10)	0.0331 (10)	0.0024 (8)	0.0050 (8)	0.0021 (8)
C1	0.0372 (10)	0.0419 (10)	0.0414 (11)	0.0068 (8)	0.0059 (8)	−0.0018 (8)
C12	0.0503 (11)	0.0537 (12)	0.0335 (11)	−0.0109 (9)	0.0044 (9)	0.0027 (9)
C22	0.0682 (14)	0.0626 (14)	0.0412 (12)	0.0153 (11)	0.0158 (10)	−0.0050 (10)
C17	0.0449 (11)	0.0635 (14)	0.0485 (13)	−0.0078 (10)	0.0150 (9)	0.0090 (10)
C19	0.0376 (10)	0.0648 (13)	0.0407 (11)	−0.0063 (9)	0.0049 (8)	−0.0020 (10)
C18	0.0406 (11)	0.0730 (15)	0.0534 (14)	−0.0165 (10)	0.0087 (9)	−0.0006 (11)
C6	0.0477 (11)	0.0738 (15)	0.0412 (12)	0.0026 (11)	0.0020 (9)	0.0061 (11)
C21	0.0835 (17)	0.0693 (15)	0.0397 (13)	−0.0016 (13)	0.0199 (12)	0.0094 (11)
C23	0.0477 (12)	0.0874 (17)	0.0450 (13)	−0.0090 (12)	−0.0078 (10)	0.0099 (12)
C2	0.0467 (12)	0.0761 (16)	0.0682 (16)	0.0043 (11)	0.0122 (11)	0.0215 (13)
C4	0.0387 (11)	0.0757 (16)	0.0765 (18)	0.0069 (11)	−0.0033 (12)	−0.0295 (14)
C5	0.0590 (14)	0.0907 (19)	0.0489 (14)	0.0113 (13)	−0.0111 (11)	−0.0079 (13)
C3	0.0445 (12)	0.0807 (18)	0.099 (2)	−0.0016 (12)	0.0204 (14)	0.0022 (16)

Geometric parameters (Å, º) top

O4—C11	1.337 (2)	C7—C1	1.506 (2)
O4—C7	1.452 (2)	C7—H7	0.9800
O2—C20	1.363 (2)	C1—C6	1.361 (3)
O2—C15	1.396 (2)	C1—C2	1.373 (3)
O3—C20	1.189 (2)	C22—H22A	0.9600
O6—C13	1.221 (2)	C22—H22C	0.9600
O5—C12	1.215 (2)	C22—H22B	0.9600
N1—C11	1.368 (2)	C17—C18	1.381 (3)
N1—C12	1.384 (3)	C17—H17	0.9300
N1—C22	1.465 (3)	C19—C18	1.376 (3)
O1—C16	1.360 (2)	C19—H19	0.9300
O1—C21	1.426 (2)	C18—H18	0.9300
N2—C12	1.376 (3)	C6—C5	1.388 (3)
N2—C13	1.398 (3)	C6—H6	0.9300
N2—C23	1.468 (2)	C21—H21A	0.9600
C13—C10	1.436 (2)	C21—H21B	0.9600
C11—C10	1.348 (3)	C21—H21C	0.9600
C14—C15	1.377 (3)	C23—H23A	0.9600
C14—C19	1.386 (3)	C23—H23B	0.9600
C14—C9	1.520 (2)	C23—H23C	0.9600
C10—C9	1.503 (3)	C2—C3	1.384 (3)
C16—C17	1.381 (3)	C2—H2	0.9300
C16—C15	1.403 (3)	C4—C5	1.349 (4)
C20—C8	1.507 (3)	C4—C3	1.366 (4)
C9—C8	1.530 (2)	C4—H4	0.9300
C9—H9	0.9800	C5—H5	0.9300
C8—C7	1.533 (3)	C3—H3	0.9300
C8—H8	0.9800

C11—O4—C7	117.97 (14)	C6—C1—C2	118.38 (19)
C20—O2—C15	120.75 (14)	C6—C1—C7	119.54 (18)
C11—N1—C12	121.34 (17)	C2—C1—C7	122.06 (18)
C11—N1—C22	121.18 (16)	O5—C12—N2	122.78 (19)
C12—N1—C22	117.46 (17)	O5—C12—N1	121.7 (2)
C16—O1—C21	117.29 (17)	N2—C12—N1	115.52 (17)
C12—N2—C13	125.11 (16)	N1—C22—H22A	109.5
C12—N2—C23	116.86 (17)	N1—C22—H22C	109.5
C13—N2—C23	118.00 (17)	H22A—C22—H22C	109.5
O6—C13—N2	119.66 (17)	N1—C22—H22B	109.5
O6—C13—C10	124.30 (18)	H22A—C22—H22B	109.5
N2—C13—C10	116.04 (17)	H22C—C22—H22B	109.5
O4—C11—C10	125.25 (17)	C18—C17—C16	120.08 (19)
O4—C11—N1	111.64 (16)	C18—C17—H17	120.0
C10—C11—N1	123.11 (17)	C16—C17—H17	120.0
C15—C14—C19	118.45 (18)	C18—C19—C14	120.33 (19)
C15—C14—C9	118.22 (16)	C18—C19—H19	119.8
C19—C14—C9	123.30 (17)	C14—C19—H19	119.8
C11—C10—C13	118.49 (17)	C19—C18—C17	120.93 (19)
C11—C10—C9	120.83 (16)	C19—C18—H18	119.5
C13—C10—C9	120.39 (16)	C17—C18—H18	119.5
O1—C16—C17	125.70 (18)	C1—C6—C5	121.1 (2)
O1—C16—C15	116.05 (17)	C1—C6—H6	119.4
C17—C16—C15	118.25 (18)	C5—C6—H6	119.4
O3—C20—O2	117.79 (17)	O1—C21—H21A	109.5
O3—C20—C8	124.59 (18)	O1—C21—H21B	109.5
O2—C20—C8	117.62 (15)	H21A—C21—H21B	109.5
C14—C15—O2	122.90 (16)	O1—C21—H21C	109.5
C14—C15—C16	121.94 (17)	H21A—C21—H21C	109.5
O2—C15—C16	115.09 (16)	H21B—C21—H21C	109.5
C10—C9—C14	115.59 (15)	N2—C23—H23A	109.5
C10—C9—C8	107.66 (14)	N2—C23—H23B	109.5
C14—C9—C8	109.55 (14)	H23A—C23—H23B	109.5
C10—C9—H9	107.9	N2—C23—H23C	109.5
C14—C9—H9	107.9	H23A—C23—H23C	109.5
C8—C9—H9	107.9	H23B—C23—H23C	109.5
C20—C8—C9	111.91 (15)	C1—C2—C3	120.3 (2)
C20—C8—C7	110.65 (15)	C1—C2—H2	119.8
C9—C8—C7	109.51 (15)	C3—C2—H2	119.8
C20—C8—H8	108.2	C5—C4—C3	119.3 (2)
C9—C8—H8	108.2	C5—C4—H4	120.3
C7—C8—H8	108.2	C3—C4—H4	120.3
O4—C7—C1	106.40 (15)	C4—C5—C6	120.3 (2)
O4—C7—C8	108.85 (14)	C4—C5—H5	119.9
C1—C7—C8	114.07 (15)	C6—C5—H5	119.9
O4—C7—H7	109.1	C4—C3—C2	120.6 (2)
C1—C7—H7	109.1	C4—C3—H3	119.7
C8—C7—H7	109.1	C2—C3—H3	119.7

Hydrogen-bond geometry (Å, º) top

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+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀N₂O₆
M_r	420.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	16.8362 (9), 8.1692 (4), 14.4400 (8)
β (°)	98.000 (3)
V (Å³)	1966.72 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker 2004)
T_min, T_max	0.979, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	19858, 4247, 2943
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.637

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.130, 1.04
No. of reflections	4247
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.19

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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+1/2, −z+1/2.

Acknowledgements

SA thanks the UGC, India, for financial support

References

Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Casley-Smith, J. R., Wang, C. T., Casley-Smith, J. R. & Zi-hai, C. (1993). Br. Med. J. 307, 1037–1041. CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Goel, R. K., Maiti, R. N., Manickam, M. & Ray, A. B. (1997). Indian J. Exp. Biol. 35, 1080–1083. CAS PubMed Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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. Web of Science CrossRef PubMed CAS Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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