14-Eth-oxy-4,6-dimethyl-9-phenyl-8,12-dioxa-4,6-diaza-tetra-cyclo-[8.8.0.0(2,7).0(13,18)]octa-deca-2(7),13,15,17-tetra-ene-3,5,11-trione.

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, mol-ecules 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 = 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

Δρmax = 0.28 e Å−3

Δρmin = −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 ▶).

Click here for additional data file.

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

Click here for additional data file.

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

Click here for additional data file.

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

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

C23H20N2O6	F(000) = 880
Mr = 420.41	Dx = 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

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

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(Fo2) + (0.0545P)2 + 0.6922P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
4247 reflections	Δρmax = 0.28 e Å−3
281 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) ; (ii) .