Cinnamyl 8-meth-oxy-2-oxo-2H-chromene-3-carboxyl-ate.

In the crystal structure of the title compound, C(20)H(16)O(5), the mol-ecule assumes an E configuration with the benzene ring and chromenecarboxyl group located on opposite ends of the C=C double bond. The chromene ring system and benzene ring are oriented at a dihedral angle of 74.66 (12)°. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of coumarins and related compounds, see: Hoult & Paya (1996 ▶); Yu et al. (2003 ▶, 2007 ▶); Finn et al. (2004 ▶).

Experimental

Crystal data

C20H16O5

M = 336.33

Monoclinic,

a = 19.226 (4) Å

b = 9.5483 (19) Å

c = 9.0046 (18) Å

β = 90.97 (3)°

V = 1652.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.20 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area detector diffractometer

Absorption correction: none

4903 measured reflections

2834 independent reflections

2157 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.155

S = 1.15

2834 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041725/xu2613sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041725/xu2613Isup2.hkl

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

C20H16O5	F(000) = 704
Mr = 336.33	Dx = 1.352 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2834 reflections
a = 19.226 (4) Å	θ = 3.1–24.2°
b = 9.5483 (19) Å	µ = 0.10 mm−1
c = 9.0046 (18) Å	T = 296 K
β = 90.97 (3)°	Block, colorless
V = 1652.8 (6) Å3	0.20 × 0.17 × 0.17 mm
Z = 4

Bruker SMART CCD area detector diffractometer	2157 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
graphite	θmax = 25.0°, θmin = 1.1°
ω scans	h = −22→22
4903 measured reflections	k = −11→11
2834 independent reflections	l = 0→10

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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.0659P)2 + 0.2012P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max = 0.001
2834 reflections	Δρmax = 0.24 e Å−3
228 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.04001 (9)	0.88854 (18)	0.70962 (19)	0.0610 (5)
O2	0.11713 (7)	0.72996 (15)	0.54027 (17)	0.0463 (4)
O3	0.15130 (10)	0.51497 (17)	0.4995 (2)	0.0705 (6)
O4	0.25790 (11)	0.4732 (2)	0.3000 (3)	0.0885 (7)
O5	0.28952 (8)	0.66346 (19)	0.17300 (19)	0.0617 (5)
C1	0.12199 (11)	0.8722 (2)	0.5210 (2)	0.0414 (6)
C2	0.08113 (11)	0.9568 (3)	0.6115 (3)	0.0497 (6)
C3	0.08597 (14)	1.0996 (3)	0.5946 (3)	0.0652 (8)
H3A	0.0593	1.1578	0.6536	0.078*
C4	0.13001 (15)	1.1585 (3)	0.4910 (3)	0.0710 (8)
H4A	0.1323	1.2554	0.4816	0.085*
C5	0.17013 (13)	1.0757 (3)	0.4023 (3)	0.0605 (7)
H5A	0.1992	1.1160	0.3328	0.073*
C6	0.16698 (11)	0.9293 (2)	0.4174 (3)	0.0445 (6)
C7	0.20856 (11)	0.8339 (2)	0.3351 (2)	0.0450 (6)
H7A	0.2383	0.8693	0.2638	0.054*
C8	0.20641 (10)	0.6940 (2)	0.3568 (2)	0.0429 (6)
C9	0.15868 (11)	0.6355 (2)	0.4665 (3)	0.0460 (6)
C10	0.25260 (12)	0.5959 (3)	0.2770 (3)	0.0525 (6)
C11	−0.00432 (15)	0.9739 (3)	0.7994 (3)	0.0743 (8)
H11A	−0.0314	0.9150	0.8626	0.112*
H11B	−0.0349	1.0278	0.7362	0.112*
H11C	0.0237	1.0360	0.8592	0.112*
C12	0.33877 (13)	0.5785 (3)	0.0894 (3)	0.0697 (8)
H12A	0.3470	0.6224	−0.0059	0.084*
H12B	0.3189	0.4867	0.0709	0.084*
C13	0.40569 (13)	0.5629 (3)	0.1714 (3)	0.0646 (7)
H13A	0.4053	0.5142	0.2608	0.078*
C14	0.46490 (14)	0.6123 (3)	0.1279 (3)	0.0639 (7)
H14A	0.4640	0.6613	0.0386	0.077*
C15	0.53343 (12)	0.6000 (3)	0.2031 (3)	0.0560 (7)
C16	0.58725 (14)	0.6863 (3)	0.1617 (4)	0.0741 (9)
H16A	0.5804	0.7481	0.0830	0.089*
C17	0.65113 (15)	0.6830 (3)	0.2345 (5)	0.0831 (10)
H17A	0.6861	0.7445	0.2067	0.100*
C18	0.66314 (14)	0.5891 (3)	0.3481 (4)	0.0741 (9)
H18A	0.7059	0.5874	0.3980	0.089*
C19	0.61138 (15)	0.4981 (4)	0.3866 (3)	0.0763 (9)
H19A	0.6195	0.4320	0.4608	0.092*
C20	0.54716 (14)	0.5041 (3)	0.3158 (3)	0.0694 (8)
H20A	0.5123	0.4426	0.3443	0.083*

	U11	U22	U33	U12	U13	U23
O1	0.0600 (10)	0.0639 (11)	0.0597 (11)	0.0079 (9)	0.0171 (8)	−0.0059 (9)
O2	0.0487 (9)	0.0410 (9)	0.0494 (10)	0.0015 (7)	0.0053 (7)	−0.0008 (7)
O3	0.0869 (14)	0.0375 (10)	0.0877 (14)	0.0016 (9)	0.0227 (10)	0.0041 (9)
O4	0.1028 (16)	0.0562 (13)	0.1075 (17)	0.0296 (11)	0.0322 (13)	0.0052 (11)
O5	0.0522 (10)	0.0719 (12)	0.0615 (12)	0.0113 (9)	0.0125 (8)	−0.0069 (9)
C1	0.0391 (12)	0.0364 (12)	0.0486 (14)	0.0004 (10)	−0.0026 (10)	−0.0021 (10)
C2	0.0444 (13)	0.0505 (15)	0.0541 (15)	0.0053 (11)	−0.0019 (11)	−0.0051 (12)
C3	0.0668 (17)	0.0523 (16)	0.0767 (19)	0.0122 (13)	0.0061 (14)	−0.0112 (14)
C4	0.0784 (19)	0.0382 (14)	0.096 (2)	0.0072 (13)	0.0005 (17)	−0.0028 (15)
C5	0.0590 (16)	0.0446 (14)	0.0783 (19)	−0.0029 (12)	0.0079 (13)	0.0063 (13)
C6	0.0394 (12)	0.0392 (12)	0.0550 (15)	0.0021 (10)	−0.0010 (10)	−0.0012 (11)
C7	0.0370 (12)	0.0503 (14)	0.0477 (14)	−0.0026 (10)	0.0007 (9)	0.0011 (11)
C8	0.0364 (12)	0.0444 (13)	0.0476 (14)	0.0026 (10)	−0.0039 (10)	−0.0026 (10)
C9	0.0472 (13)	0.0401 (14)	0.0506 (15)	0.0028 (10)	−0.0024 (10)	−0.0044 (11)
C10	0.0470 (14)	0.0573 (16)	0.0531 (16)	0.0102 (12)	−0.0031 (11)	−0.0058 (13)
C11	0.0676 (18)	0.090 (2)	0.0663 (19)	0.0167 (16)	0.0152 (14)	−0.0173 (16)
C12	0.0520 (16)	0.093 (2)	0.0642 (18)	0.0203 (14)	0.0082 (13)	−0.0162 (16)
C13	0.0517 (15)	0.0826 (19)	0.0598 (17)	0.0113 (14)	0.0072 (12)	−0.0058 (15)
C14	0.0605 (16)	0.0681 (17)	0.0635 (17)	0.0112 (14)	0.0127 (13)	−0.0002 (14)
C15	0.0484 (14)	0.0513 (14)	0.0690 (18)	0.0042 (12)	0.0139 (12)	−0.0074 (13)
C16	0.0617 (18)	0.0521 (16)	0.109 (2)	0.0106 (14)	0.0295 (16)	0.0079 (16)
C17	0.0542 (18)	0.0535 (17)	0.143 (3)	−0.0068 (14)	0.0329 (18)	−0.012 (2)
C18	0.0490 (16)	0.078 (2)	0.096 (2)	0.0006 (15)	0.0078 (15)	−0.0310 (19)
C19	0.0669 (18)	0.091 (2)	0.071 (2)	0.0004 (17)	0.0080 (15)	0.0048 (16)
C20	0.0549 (16)	0.0741 (19)	0.080 (2)	−0.0136 (14)	0.0122 (14)	0.0070 (16)

O1—C2	1.362 (3)	C11—H11A	0.9600
O1—C11	1.438 (3)	C11—H11B	0.9600
O2—C1	1.373 (3)	C11—H11C	0.9600
O2—C9	1.382 (3)	C12—C13	1.480 (4)
O3—C9	1.198 (3)	C12—H12A	0.9700
O4—C10	1.194 (3)	C12—H12B	0.9700
O5—C10	1.349 (3)	C13—C14	1.299 (4)
O5—C12	1.465 (3)	C13—H13A	0.9300
C1—C6	1.394 (3)	C14—C15	1.476 (4)
C1—C2	1.398 (3)	C14—H14A	0.9300
C2—C3	1.375 (4)	C15—C16	1.379 (3)
C3—C4	1.389 (4)	C15—C20	1.389 (4)
C3—H3A	0.9300	C16—C17	1.383 (4)
C4—C5	1.370 (4)	C16—H16A	0.9300
C4—H4A	0.9300	C17—C18	1.377 (4)
C5—C6	1.405 (3)	C17—H17A	0.9300
C5—H5A	0.9300	C18—C19	1.370 (4)
C6—C7	1.428 (3)	C18—H18A	0.9300
C7—C8	1.351 (3)	C19—C20	1.381 (4)
C7—H7A	0.9300	C19—H19A	0.9300
C8—C9	1.469 (3)	C20—H20A	0.9300
C8—C10	1.485 (3)
C2—O1—C11	116.7 (2)	H11A—C11—H11B	109.5
C1—O2—C9	122.93 (18)	O1—C11—H11C	109.5
C10—O5—C12	116.4 (2)	H11A—C11—H11C	109.5
O2—C1—C6	121.0 (2)	H11B—C11—H11C	109.5
O2—C1—C2	117.3 (2)	O5—C12—C13	111.3 (2)
C6—C1—C2	121.7 (2)	O5—C12—H12A	109.4
O1—C2—C3	126.0 (2)	C13—C12—H12A	109.4
O1—C2—C1	116.1 (2)	O5—C12—H12B	109.4
C3—C2—C1	117.9 (2)	C13—C12—H12B	109.4
C2—C3—C4	121.3 (3)	H12A—C12—H12B	108.0
C2—C3—H3A	119.4	C14—C13—C12	124.9 (3)
C4—C3—H3A	119.4	C14—C13—H13A	117.6
C5—C4—C3	120.9 (2)	C12—C13—H13A	117.6
C5—C4—H4A	119.6	C13—C14—C15	127.8 (3)
C3—C4—H4A	119.6	C13—C14—H14A	116.1
C4—C5—C6	119.5 (2)	C15—C14—H14A	116.1
C4—C5—H5A	120.3	C16—C15—C20	117.2 (3)
C6—C5—H5A	120.3	C16—C15—C14	119.8 (3)
C1—C6—C5	118.8 (2)	C20—C15—C14	123.0 (2)
C1—C6—C7	117.2 (2)	C15—C16—C17	121.5 (3)
C5—C6—C7	124.0 (2)	C15—C16—H16A	119.2
C8—C7—C6	122.5 (2)	C17—C16—H16A	119.2
C8—C7—H7A	118.7	C18—C17—C16	120.2 (3)
C6—C7—H7A	118.7	C18—C17—H17A	119.9
C7—C8—C9	119.6 (2)	C16—C17—H17A	119.9
C7—C8—C10	122.2 (2)	C19—C18—C17	119.2 (3)
C9—C8—C10	118.1 (2)	C19—C18—H18A	120.4
O3—C9—O2	115.8 (2)	C17—C18—H18A	120.4
O3—C9—C8	127.6 (2)	C18—C19—C20	120.3 (3)
O2—C9—C8	116.62 (19)	C18—C19—H19A	119.9
O4—C10—O5	123.1 (2)	C20—C19—H19A	119.9
O4—C10—C8	125.8 (3)	C19—C20—C15	121.5 (3)
O5—C10—C8	111.2 (2)	C19—C20—H20A	119.3
O1—C11—H11A	109.5	C15—C20—H20A	119.3
O1—C11—H11B	109.5
C9—O2—C1—C6	4.0 (3)	C7—C8—C9—O3	−179.1 (2)
C9—O2—C1—C2	−174.71 (19)	C10—C8—C9—O3	−1.1 (3)
C11—O1—C2—C3	2.6 (4)	C7—C8—C9—O2	1.1 (3)
C11—O1—C2—C1	−177.7 (2)	C10—C8—C9—O2	179.11 (18)
O2—C1—C2—O1	−0.4 (3)	C12—O5—C10—O4	−1.3 (3)
C6—C1—C2—O1	−179.15 (19)	C12—O5—C10—C8	178.20 (18)
O2—C1—C2—C3	179.3 (2)	C7—C8—C10—O4	172.9 (3)
C6—C1—C2—C3	0.6 (3)	C9—C8—C10—O4	−5.0 (4)
O1—C2—C3—C4	179.8 (2)	C7—C8—C10—O5	−6.5 (3)
C1—C2—C3—C4	0.0 (4)	C9—C8—C10—O5	175.55 (18)
C2—C3—C4—C5	−0.1 (4)	C10—O5—C12—C13	−83.6 (3)
C3—C4—C5—C6	−0.5 (4)	O5—C12—C13—C14	−115.1 (3)
O2—C1—C6—C5	−179.8 (2)	C12—C13—C14—C15	−179.5 (3)
C2—C1—C6—C5	−1.2 (3)	C13—C14—C15—C16	−164.1 (3)
O2—C1—C6—C7	−1.3 (3)	C13—C14—C15—C20	15.9 (4)
C2—C1—C6—C7	177.37 (19)	C20—C15—C16—C17	−3.4 (4)
C4—C5—C6—C1	1.1 (4)	C14—C15—C16—C17	176.6 (3)
C4—C5—C6—C7	−177.4 (2)	C15—C16—C17—C18	2.2 (4)
C1—C6—C7—C8	−1.3 (3)	C16—C17—C18—C19	0.7 (4)
C5—C6—C7—C8	177.1 (2)	C17—C18—C19—C20	−2.3 (4)
C6—C7—C8—C9	1.4 (3)	C18—C19—C20—C15	0.9 (4)
C6—C7—C8—C10	−176.50 (19)	C16—C15—C20—C19	1.9 (4)
C1—O2—C9—O3	176.3 (2)	C14—C15—C20—C19	−178.2 (3)
C1—O2—C9—C8	−3.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O3i	0.93	2.51	3.429 (3)	170
C17—H17A···O4ii	0.93	2.44	3.294 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O3i	0.93	2.51	3.429 (3)	170
C17—H17A⋯O4ii	0.93	2.44	3.294 (4)	153

Symmetry codes: (i) ; (ii) .