14-Eth­oxy-4,6,9-trimethyl-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/S1600536813000743

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o272

doi:10.1107/S1600536813000743

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14-Ethoxy-4,6,9-trimethyl-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 2 December 2012; accepted 8 January 2013; online 23 January 2013)

In the title compound, C₁₉H₂₀N₂O₆, the pyrone and pyran rings adopt envelope conformations with the same common C atom as the flap, the dihedral angle between the planes of the remaining ring atoms being 68.27 (4)°. The planar atoms of the pyran ring and the diazacyclic ring are almost coplanar, the dihedral angle between their mean planes being 3.29 (7)°. Moreover, the planar atoms of the pyrone ring and benzene ring of the coumarin unit are also close to coplanar, the dihedral angle between their mean planes being 8.03 (9)°. The methoxy group lies in the plane of the benzene ring, with a dihedral angle between their mean planes of 9.4 (2)°. In the crystal, the molecules are linked by C—H⋯O hydrogen bonds resulting in sheets of molecules in the ac plane.

Related literature

For the biological activity of pyranocoumarin compounds, see: Kawaii et al. (2001 ); Goel et al. (1997 ); Su et al. (2009 ). For a related structure, see: Pojarová et al. (2012 ).

Experimental

Crystal data

C₁₉H₂₀N₂O₆
M_r = 372.37
Monoclinic, P 2₁ /n
a = 9.3526 (3) Å
b = 17.9559 (5) Å
c = 10.9158 (3) Å
β = 101.346 (1)°
V = 1797.31 (9) 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
21571 measured reflections
5615 independent reflections
3743 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.151
S = 1.03
5615 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O6ⁱ	0.98	2.40	3.1480 (17)	132
C18—H18C⋯O3ⁱⁱ	0.96	2.45	3.252 (2)	140
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z+1.

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: 10.1107/S1600536813000743/pv2613sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000743/pv2613Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813000743/pv2613Isup3.cml

checkCIF report

Comment top

Coumarin derivatives show strong activity against cancer cell lines (Kawaii et al., 2001) and exhibit antiulcer (Goel et al., 1997) and cytotoxic activities (Su et al., 2009). We report here in this paper the crystal structure of the title coumarin derivative.

In the title molecule (Fig. 1), the pyrone (O2/C3/C4/C9/C10/C15) and pyran (O4/C2–C6) rings adopt C3-envelope conformations with C3 displaced by 0.603 (2) and 0.668 (2) Å, respectively, from the least-square planes formed by the remaining ring atoms; the dihedral angle between the two mean-planes being 68.27 (4)°. The planar atoms of the pyran ring (O4/C2/C4–C6) and diazacyclic ring (N1/N2/C5–C8) are almost co-planar with dihedral angle between the mean-planes being 3.29 (7)°. Moreover, the planar atoms of the pyrone ring (O2/C4/C9/C10/C15) and benzene ring (C9–C14) of the coumarin moiety are also co-planar with dihedral angle between the mean-planes being 8.03 (9)°. The methoxy group (O1/C16/C17) lies in the plane of the benzene ring (C9–C14) with a dihedral angle between the mean-planes 9.4 (2)°. The crystal packing is stabilized by intermolecular C2—H2···O6 and C18—H18C···O3 hydrogen bonding interactions (Fig. 2 and Table 1).

Related literature top

For the biological activity of pyranocoumarin compounds, see: Kawaii et al. (2001); Goel et al. (1997); Su et al. (2009). For a related structure, see: Pojarová et al. (2012).

Experimental top

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 14-Ethoxy-4,6,9-trimethyl-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-trione180 °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.

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 compound, Displacement ellipsoids are drawn at the 30% probability level, H atoms have been omitted for clarity.
	Fig. 2. Crystal packing of the title compound, Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms not involved in the interactions have been omitted.

14-Ethoxy-4,6,9-trimethyl-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

C₁₉H₂₀N₂O₆	F(000) = 784
M_r = 372.37	D_x = 1.376 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8834 reflections
a = 9.3526 (3) Å	θ = 2.1–31.2°
b = 17.9559 (5) Å	µ = 0.10 mm⁻¹
c = 10.9158 (3) Å	T = 293 K
β = 101.346 (1)°	Block, colourless
V = 1797.31 (9) Å³	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	5615 independent reflections
Radiation source: fine-focus sealed tube	3743 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scan	θ_max = 31.2°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −13→13
T_min = 0.979, T_max = 0.983	k = −26→25
21571 measured reflections	l = −15→9

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.151	w = 1/[σ²(F_o²) + (0.0701P)² + 0.3178P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5615 reflections	Δρ_max = 0.31 e Å⁻³
245 parameters	Δρ_min = −0.20 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: 0.0038 (11)

Crystal data top

C₁₉H₂₀N₂O₆	V = 1797.31 (9) Å³
M_r = 372.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.3526 (3) Å	µ = 0.10 mm⁻¹
b = 17.9559 (5) Å	T = 293 K
c = 10.9158 (3) Å	0.25 × 0.20 × 0.20 mm
β = 101.346 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5615 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2004)	3743 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.983	R_int = 0.024
21571 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.03	Δρ_max = 0.31 e Å⁻³
5615 reflections	Δρ_min = −0.20 e Å⁻³
245 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
C4	0.13936 (13)	0.22959 (7)	0.17644 (11)	0.0356 (3)
H4	0.2334	0.2050	0.2061	0.043*
O2	0.12546 (11)	0.18881 (6)	−0.07686 (9)	0.0488 (3)
O4	−0.00265 (11)	0.37272 (5)	0.16207 (10)	0.0509 (3)
C3	0.15760 (13)	0.28831 (7)	0.07958 (12)	0.0385 (3)
H3	0.2385	0.3211	0.1163	0.046*
C5	0.09372 (13)	0.26778 (7)	0.28399 (12)	0.0383 (3)
N1	0.07800 (14)	0.27406 (8)	0.50011 (11)	0.0533 (3)
O3	0.27612 (11)	0.27910 (7)	−0.09473 (10)	0.0570 (3)
O6	0.18464 (12)	0.17436 (7)	0.42755 (10)	0.0582 (3)
C9	0.03042 (13)	0.17227 (7)	0.11316 (12)	0.0359 (3)
N2	−0.01928 (14)	0.37032 (8)	0.36503 (13)	0.0546 (3)
C2	0.01853 (15)	0.33507 (7)	0.04908 (13)	0.0423 (3)
H2	−0.0645	0.3019	0.0203	0.051*
C6	0.02593 (14)	0.33416 (8)	0.26892 (13)	0.0429 (3)
C8	0.12327 (14)	0.23418 (9)	0.40514 (12)	0.0443 (3)
C15	0.19303 (14)	0.25353 (8)	−0.03619 (12)	0.0422 (3)
C10	0.02937 (14)	0.15529 (7)	−0.01043 (12)	0.0394 (3)
C11	−0.06657 (16)	0.10293 (8)	−0.07638 (13)	0.0454 (3)
C14	−0.07055 (15)	0.13790 (8)	0.17140 (13)	0.0433 (3)
H14	−0.0734	0.1493	0.2540	0.052*
O1	−0.05510 (14)	0.09050 (6)	−0.19682 (10)	0.0605 (3)
C12	−0.16431 (17)	0.06843 (8)	−0.01514 (15)	0.0517 (4)
H12	−0.2285	0.0328	−0.0563	0.062*
C13	−0.16670 (17)	0.08690 (8)	0.10732 (15)	0.0516 (4)
H13	−0.2346	0.0644	0.1471	0.062*
C16	−0.13766 (19)	0.03015 (9)	−0.26109 (15)	0.0594 (4)
H16A	−0.2410	0.0417	−0.2766	0.071*
H16B	−0.1213	−0.0149	−0.2113	0.071*
C7	0.00306 (18)	0.33991 (11)	0.48375 (16)	0.0592 (4)
O5	−0.04221 (16)	0.37072 (9)	0.56792 (13)	0.0855 (5)
C18	0.1006 (2)	0.24059 (13)	0.62469 (15)	0.0734 (5)
H18A	0.1538	0.1948	0.6249	0.110*
H18B	0.0079	0.2307	0.6464	0.110*
H18C	0.1551	0.2743	0.6845	0.110*
C17	−0.0879 (2)	0.01967 (12)	−0.38124 (18)	0.0775 (6)
H17A	−0.1412	−0.0205	−0.4270	0.116*
H17B	0.0144	0.0082	−0.3646	0.116*
H17C	−0.1047	0.0646	−0.4297	0.116*
C19	−0.1050 (2)	0.43883 (11)	0.3431 (2)	0.0813 (6)
H19A	−0.1135	0.4538	0.2575	0.122*
H19B	−0.0574	0.4774	0.3969	0.122*
H19C	−0.2004	0.4302	0.3603	0.122*
C1	0.0188 (2)	0.39517 (9)	−0.04694 (17)	0.0625 (4)
H1A	−0.0728	0.4211	−0.0608	0.094*
H1C	0.0328	0.3732	−0.1238	0.094*
H1B	0.0964	0.4296	−0.0175	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C4	0.0312 (5)	0.0409 (6)	0.0348 (6)	0.0038 (5)	0.0069 (5)	0.0008 (5)
O2	0.0530 (6)	0.0568 (6)	0.0407 (5)	−0.0071 (5)	0.0197 (4)	−0.0078 (4)
O4	0.0557 (6)	0.0419 (5)	0.0550 (6)	0.0095 (4)	0.0102 (5)	−0.0018 (4)
C3	0.0338 (6)	0.0433 (7)	0.0378 (6)	−0.0037 (5)	0.0056 (5)	0.0004 (5)
C5	0.0337 (6)	0.0455 (7)	0.0354 (6)	−0.0006 (5)	0.0063 (5)	−0.0050 (5)
N1	0.0478 (7)	0.0770 (9)	0.0351 (6)	−0.0090 (6)	0.0083 (5)	−0.0115 (6)
O3	0.0472 (6)	0.0811 (8)	0.0460 (6)	−0.0100 (5)	0.0172 (5)	0.0057 (5)
O6	0.0537 (6)	0.0729 (7)	0.0452 (6)	0.0102 (6)	0.0027 (5)	0.0103 (5)
C9	0.0362 (6)	0.0346 (6)	0.0373 (6)	0.0044 (5)	0.0082 (5)	−0.0003 (5)
N2	0.0510 (7)	0.0551 (8)	0.0589 (8)	0.0028 (6)	0.0140 (6)	−0.0192 (6)
C2	0.0408 (7)	0.0396 (7)	0.0446 (7)	0.0010 (5)	0.0035 (5)	0.0017 (5)
C6	0.0367 (6)	0.0453 (7)	0.0464 (7)	−0.0019 (5)	0.0073 (5)	−0.0100 (6)
C8	0.0331 (6)	0.0612 (9)	0.0368 (6)	−0.0047 (6)	0.0026 (5)	−0.0045 (6)
C15	0.0351 (6)	0.0540 (8)	0.0373 (6)	0.0001 (6)	0.0069 (5)	0.0043 (6)
C10	0.0416 (7)	0.0382 (6)	0.0402 (6)	0.0013 (5)	0.0126 (5)	−0.0017 (5)
C11	0.0527 (8)	0.0407 (7)	0.0418 (7)	0.0033 (6)	0.0071 (6)	−0.0053 (6)
C14	0.0458 (7)	0.0429 (7)	0.0433 (7)	−0.0003 (6)	0.0135 (6)	0.0008 (6)
O1	0.0773 (8)	0.0580 (7)	0.0462 (6)	−0.0103 (6)	0.0123 (5)	−0.0163 (5)
C12	0.0510 (8)	0.0416 (7)	0.0601 (9)	−0.0067 (6)	0.0052 (7)	−0.0045 (7)
C13	0.0511 (8)	0.0475 (8)	0.0588 (9)	−0.0084 (6)	0.0172 (7)	0.0019 (7)
C16	0.0656 (10)	0.0489 (8)	0.0585 (9)	0.0060 (7)	−0.0005 (7)	−0.0188 (7)
C7	0.0491 (8)	0.0773 (11)	0.0524 (9)	−0.0082 (8)	0.0126 (7)	−0.0248 (8)
O5	0.0845 (9)	0.1113 (11)	0.0661 (8)	0.0010 (8)	0.0283 (7)	−0.0401 (8)
C18	0.0725 (11)	0.1111 (16)	0.0368 (8)	−0.0087 (11)	0.0110 (8)	−0.0010 (9)
C17	0.0926 (14)	0.0744 (12)	0.0624 (11)	0.0085 (11)	0.0076 (10)	−0.0287 (10)
C19	0.0893 (14)	0.0655 (11)	0.0923 (15)	0.0240 (10)	0.0258 (11)	−0.0246 (11)
C1	0.0695 (11)	0.0531 (9)	0.0621 (10)	0.0046 (8)	0.0062 (8)	0.0156 (8)

Geometric parameters (Å, º) top

C4—C5	1.4926 (18)	C10—C11	1.3975 (19)
C4—C9	1.5157 (17)	C11—O1	1.3584 (17)
C4—C3	1.5263 (18)	C11—C12	1.381 (2)
C4—H4	0.9800	C14—C13	1.374 (2)
O2—C15	1.3552 (17)	C14—H14	0.9300
O2—C10	1.3972 (16)	O1—C16	1.4316 (18)
O4—C6	1.3373 (18)	C12—C13	1.382 (2)
O4—C2	1.4538 (17)	C12—H12	0.9300
C3—C15	1.5038 (19)	C13—H13	0.9300
C3—C2	1.5288 (18)	C16—C17	1.487 (3)
C3—H3	0.9800	C16—H16A	0.9700
C5—C6	1.3448 (19)	C16—H16B	0.9700
C5—C8	1.4301 (19)	C7—O5	1.2175 (19)
N1—C7	1.368 (2)	C18—H18A	0.9600
N1—C8	1.3926 (19)	C18—H18B	0.9600
N1—C18	1.464 (2)	C18—H18C	0.9600
O3—C15	1.1910 (16)	C17—H17A	0.9600
O6—C8	1.2197 (19)	C17—H17B	0.9600
C9—C10	1.3812 (18)	C17—H17C	0.9600
C9—C14	1.3832 (18)	C19—H19A	0.9600
N2—C6	1.3695 (18)	C19—H19B	0.9600
N2—C7	1.384 (2)	C19—H19C	0.9600
N2—C19	1.462 (2)	C1—H1A	0.9600
C2—C1	1.505 (2)	C1—H1C	0.9600
C2—H2	0.9800	C1—H1B	0.9600

C5—C4—C9	113.56 (10)	O1—C11—C10	116.37 (13)
C5—C4—C3	108.40 (11)	C12—C11—C10	118.13 (13)
C9—C4—C3	108.06 (10)	C13—C14—C9	120.06 (13)
C5—C4—H4	108.9	C13—C14—H14	120.0
C9—C4—H4	108.9	C9—C14—H14	120.0
C3—C4—H4	108.9	C11—O1—C16	117.45 (13)
C15—O2—C10	120.36 (10)	C11—C12—C13	119.93 (13)
C6—O4—C2	117.52 (10)	C11—C12—H12	120.0
C15—C3—C4	111.61 (11)	C13—C12—H12	120.0
C15—C3—C2	111.33 (11)	C14—C13—C12	121.25 (14)
C4—C3—C2	108.91 (10)	C14—C13—H13	119.4
C15—C3—H3	108.3	C12—C13—H13	119.4
C4—C3—H3	108.3	O1—C16—C17	107.20 (15)
C2—C3—H3	108.3	O1—C16—H16A	110.3
C6—C5—C8	119.19 (13)	C17—C16—H16A	110.3
C6—C5—C4	120.79 (12)	O1—C16—H16B	110.3
C8—C5—C4	120.02 (12)	C17—C16—H16B	110.3
C7—N1—C8	124.76 (13)	H16A—C16—H16B	108.5
C7—N1—C18	116.92 (14)	O5—C7—N1	122.64 (18)
C8—N1—C18	118.10 (16)	O5—C7—N2	121.11 (18)
C10—C9—C14	118.43 (12)	N1—C7—N2	116.25 (13)
C10—C9—C4	118.03 (11)	N1—C18—H18A	109.5
C14—C9—C4	123.51 (11)	N1—C18—H18B	109.5
C6—N2—C7	121.19 (14)	H18A—C18—H18B	109.5
C6—N2—C19	121.01 (15)	N1—C18—H18C	109.5
C7—N2—C19	117.55 (14)	H18A—C18—H18C	109.5
O4—C2—C1	106.06 (12)	H18B—C18—H18C	109.5
O4—C2—C3	108.82 (10)	C16—C17—H17A	109.5
C1—C2—C3	115.33 (13)	C16—C17—H17B	109.5
O4—C2—H2	108.8	H17A—C17—H17B	109.5
C1—C2—H2	108.8	C16—C17—H17C	109.5
C3—C2—H2	108.8	H17A—C17—H17C	109.5
O4—C6—C5	125.03 (13)	H17B—C17—H17C	109.5
O4—C6—N2	112.57 (12)	N2—C19—H19A	109.5
C5—C6—N2	122.39 (14)	N2—C19—H19B	109.5
O6—C8—N1	120.23 (13)	H19A—C19—H19B	109.5
O6—C8—C5	123.69 (13)	N2—C19—H19C	109.5
N1—C8—C5	116.08 (13)	H19A—C19—H19C	109.5
O3—C15—O2	117.79 (13)	H19B—C19—H19C	109.5
O3—C15—C3	124.45 (13)	C2—C1—H1A	109.5
O2—C15—C3	117.76 (11)	C2—C1—H1C	109.5
C9—C10—O2	122.01 (12)	H1A—C1—H1C	109.5
C9—C10—C11	122.15 (13)	C2—C1—H1B	109.5
O2—C10—C11	115.83 (12)	H1A—C1—H1B	109.5
O1—C11—C12	125.50 (13)	H1C—C1—H1B	109.5

C5—C4—C3—C15	−175.85 (10)	C4—C5—C8—N1	179.44 (11)
C9—C4—C3—C15	−52.37 (13)	C10—O2—C15—O3	178.55 (12)
C5—C4—C3—C2	−52.53 (13)	C10—O2—C15—C3	−1.65 (18)
C9—C4—C3—C2	70.95 (13)	C4—C3—C15—O3	−141.90 (14)
C9—C4—C5—C6	−96.05 (15)	C2—C3—C15—O3	96.17 (16)
C3—C4—C5—C6	24.06 (16)	C4—C3—C15—O2	38.32 (15)
C9—C4—C5—C8	84.60 (14)	C2—C3—C15—O2	−83.61 (14)
C3—C4—C5—C8	−155.30 (11)	C14—C9—C10—O2	178.53 (12)
C5—C4—C9—C10	155.04 (11)	C4—C9—C10—O2	0.45 (18)
C3—C4—C9—C10	34.75 (15)	C14—C9—C10—C11	−2.3 (2)
C5—C4—C9—C14	−22.92 (17)	C4—C9—C10—C11	179.67 (12)
C3—C4—C9—C14	−143.22 (12)	C15—O2—C10—C9	−19.32 (19)
C6—O4—C2—C1	−165.09 (12)	C15—O2—C10—C11	161.42 (12)
C6—O4—C2—C3	−40.44 (15)	C9—C10—C11—O1	−179.05 (12)
C15—C3—C2—O4	−174.74 (11)	O2—C10—C11—O1	0.21 (18)
C4—C3—C2—O4	61.77 (13)	C9—C10—C11—C12	1.0 (2)
C15—C3—C2—C1	−55.75 (16)	O2—C10—C11—C12	−179.70 (13)
C4—C3—C2—C1	−179.23 (12)	C10—C9—C14—C13	1.5 (2)
C2—O4—C6—C5	10.88 (19)	C4—C9—C14—C13	179.43 (13)
C2—O4—C6—N2	−170.26 (11)	C12—C11—O1—C16	−8.5 (2)
C8—C5—C6—O4	177.18 (12)	C10—C11—O1—C16	171.64 (13)
C4—C5—C6—O4	−2.2 (2)	O1—C11—C12—C13	−178.93 (14)
C8—C5—C6—N2	−1.6 (2)	C10—C11—C12—C13	1.0 (2)
C4—C5—C6—N2	179.07 (12)	C9—C14—C13—C12	0.5 (2)
C7—N2—C6—O4	−178.82 (13)	C11—C12—C13—C14	−1.7 (2)
C19—N2—C6—O4	7.1 (2)	C11—O1—C16—C17	−170.40 (14)
C7—N2—C6—C5	0.1 (2)	C8—N1—C7—O5	175.43 (15)
C19—N2—C6—C5	−174.03 (15)	C18—N1—C7—O5	0.9 (2)
C7—N1—C8—O6	−177.10 (14)	C8—N1—C7—N2	−4.5 (2)
C18—N1—C8—O6	−2.6 (2)	C18—N1—C7—N2	−179.10 (14)
C7—N1—C8—C5	3.1 (2)	C6—N2—C7—O5	−177.11 (15)
C18—N1—C8—C5	177.62 (13)	C19—N2—C7—O5	−2.8 (2)
C6—C5—C8—O6	−179.70 (13)	C6—N2—C7—N1	2.9 (2)
C4—C5—C8—O6	−0.3 (2)	C19—N2—C7—N1	177.15 (15)
C6—C5—C8—N1	0.07 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6ⁱ	0.98	2.40	3.1480 (17)	132
C18—H18C···O3ⁱⁱ	0.96	2.45	3.252 (2)	140

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀N₂O₆
M_r	372.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.3526 (3), 17.9559 (5), 10.9158 (3)
β (°)	101.346 (1)
V (Å³)	1797.31 (9)
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 diffractometer
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	21571, 5615, 3743
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.729

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.151, 1.03
No. of reflections	5615
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.20

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
C2—H2···O6ⁱ	0.98	2.40	3.1480 (17)	132.3
C18—H18C···O3ⁱⁱ	0.96	2.45	3.252 (2)	140.4

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x, y, z+1.

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
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
Kawaii, S., Tomono, Y., Ogawa, K., Sugiura, M., Yano, M., Yoshizawa, Y., Ito, C. & Furukawa, H. (2001). Anticancer Res. 21, 1905–1911. Web of Science PubMed CAS Google Scholar
Pojarová, M., Dušek, M., Sedláková, Z. & Makrlík, E. (2012). Acta Cryst. E68, o805–o806. CSD CrossRef IUCr Journals Google Scholar
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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Volume 69| Part 2| February 2013| Page o272

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

14-Eth­­oxy-4,6,9-tri­methyl-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-4,6,9-trimethyl-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