Cinnamyl 2-oxo-2H-chromene-3-carboxyl-ate.

The title compound, C(19)H(14)O(4), was prepared by the reaction of 2-oxo-2H-chromene-3-acyl chloride with cinnamic alcohol. The whole mol-ecule is not planar, the dihedral angle between the planes of coumarin and benzene rings being 13.94 (4)°, but the plane of the coumarin ring and that of the ester group are almost coplanar, making a dihedral angle of 2.9 (1)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link two mol-ecules into dimers, and π-π stacking inter-actions between inversion-related rings of the coumarin groups [centroid-centroid distance 3.8380 (15) Å with a slippage of 1.535 Å], which connect the dimers into columns extending along [010].

Related literature

For the medicinal and biological activity of coumarins and their derivatives, see: Borges et al. (2005 ▶); Kontogiorgis & Hadjipavlou-Litina (2005 ▶); Gursoy & Karali (2003 ▶). For the development of coumarin derivatives as anti-HIV agents, see: Yu et al. (2003 ▶, 2007 ▶). For the structure of menthyl 2-oxo-2H-chromene-3-carboxyl­ate, see: Xu et al. (2009 ▶).

Experimental

Crystal data

C19H14O4

M = 306.30

Monoclinic,

a = 5.7026 (11) Å

b = 8.2969 (17) Å

c = 31.693 (6) Å

β = 92.96 (3)°

V = 1497.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 291 K

0.20 × 0.18 × 0.18 mm

Data collection

Rigaku R-AXIS-IV diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.981, T max = 0.983

4266 measured reflections

2485 independent reflections

2002 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.147

S = 1.08

2485 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: R-AXIS (Rigaku, 1997 ▶); cell refinement: R-AXIS data reduction: R-AXIS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and DIAMOND (Brandenburg, 2005 ▶); software used to prepare material for publication: TEXSAN (Molecular Structure Corporation & Rigaku, 2000 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045644/si2212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045644/si2212Isup2.hkl

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

C19H14O4	F(000) = 640
Mr = 306.30	Dx = 1.359 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 378 reflections
a = 5.7026 (11) Å	θ = 1.3–25.0°
b = 8.2969 (17) Å	µ = 0.10 mm−1
c = 31.693 (6) Å	T = 291 K
β = 92.96 (3)°	Block, colourless
V = 1497.5 (5) Å3	0.20 × 0.18 × 0.18 mm
Z = 4

Rigaku R-AXIS-IV diffractometer	2485 independent reflections
Radiation source: fine-focus sealed tube	2002 reflections with I > 2σ(I)
graphite	Rint = 0.060
Detector resolution: 0 pixels mm-1	θmax = 25.0°, θmin = 1.3°
Oscillation frames scans	h = 0→6
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −9→9
Tmin = 0.981, Tmax = 0.983	l = −37→37
4266 measured reflections

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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0708P)2 + 0.2535P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2485 reflections	Δρmax = 0.24 e Å−3
209 parameters	Δρmin = −0.22 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: 0.044 (4)

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
O1	−0.2090 (3)	0.32886 (19)	0.02988 (4)	0.0567 (4)
O2	−0.1217 (3)	0.2749 (2)	0.09679 (5)	0.0696 (5)
O3	0.4778 (3)	0.0109 (2)	0.06191 (4)	0.0638 (5)
O4	0.2725 (3)	0.09462 (19)	0.11589 (4)	0.0534 (4)
C1	−0.1652 (4)	0.3240 (3)	−0.01256 (6)	0.0470 (5)
C2	−0.3243 (4)	0.4004 (3)	−0.04038 (7)	0.0621 (6)
H2A	−0.4552	0.4528	−0.0306	0.075*
C3	−0.2838 (5)	0.3967 (3)	−0.08278 (7)	0.0638 (7)
H3A	−0.3886	0.4483	−0.1018	0.077*
C4	−0.0916 (4)	0.3184 (3)	−0.09790 (7)	0.0623 (7)
H4A	−0.0674	0.3179	−0.1267	0.075*
C5	0.0644 (4)	0.2410 (3)	−0.07000 (6)	0.0557 (6)
H5A	0.1928	0.1867	−0.0801	0.067*
C6	0.0297 (3)	0.2440 (2)	−0.02644 (6)	0.0438 (5)
C7	0.1821 (4)	0.1682 (3)	0.00463 (6)	0.0445 (5)
H7A	0.3137	0.1139	−0.0041	0.053*
C8	0.1425 (3)	0.1722 (2)	0.04622 (6)	0.0421 (5)
C9	−0.0628 (4)	0.2578 (3)	0.06115 (6)	0.0493 (5)
C10	0.3154 (4)	0.0854 (3)	0.07502 (6)	0.0451 (5)
C11	0.4328 (4)	0.0061 (3)	0.14417 (6)	0.0581 (6)
H11A	0.5829	0.0613	0.1468	0.070*
H11B	0.4586	−0.1009	0.1329	0.070*
C12	0.3306 (4)	−0.0062 (3)	0.18634 (6)	0.0532 (6)
H12A	0.4147	−0.0667	0.2067	0.064*
C13	0.1334 (4)	0.0596 (3)	0.19788 (6)	0.0483 (5)
H13A	0.0479	0.1190	0.1775	0.058*
C14	0.0349 (4)	0.0481 (2)	0.24006 (6)	0.0448 (5)
C15	−0.1666 (4)	0.1337 (3)	0.24838 (7)	0.0557 (6)
H15A	−0.2359	0.1990	0.2274	0.067*
C16	−0.2664 (4)	0.1240 (3)	0.28701 (7)	0.0643 (7)
H16A	−0.4015	0.1826	0.2918	0.077*
C17	−0.1661 (4)	0.0276 (3)	0.31857 (7)	0.0610 (7)
H17A	−0.2350	0.0190	0.3444	0.073*
C18	0.0363 (5)	−0.0556 (3)	0.31136 (7)	0.0592 (6)
H18A	0.1065	−0.1187	0.3327	0.071*
C19	0.1365 (4)	−0.0463 (3)	0.27266 (6)	0.0530 (6)
H19A	0.2733	−0.1036	0.2682	0.064*

	U11	U22	U33	U12	U13	U23
O1	0.0587 (9)	0.0672 (10)	0.0450 (8)	0.0205 (8)	0.0100 (7)	−0.0005 (7)
O2	0.0735 (11)	0.0936 (13)	0.0434 (8)	0.0265 (10)	0.0188 (8)	−0.0040 (8)
O3	0.0654 (10)	0.0836 (12)	0.0431 (8)	0.0282 (9)	0.0102 (7)	−0.0002 (8)
O4	0.0606 (9)	0.0657 (10)	0.0341 (7)	0.0156 (8)	0.0053 (6)	−0.0006 (7)
C1	0.0493 (12)	0.0461 (12)	0.0459 (11)	0.0017 (10)	0.0064 (9)	0.0010 (9)
C2	0.0594 (14)	0.0684 (16)	0.0585 (14)	0.0179 (12)	0.0030 (11)	0.0045 (12)
C3	0.0639 (15)	0.0732 (16)	0.0535 (13)	0.0069 (13)	−0.0047 (11)	0.0118 (12)
C4	0.0654 (15)	0.0820 (18)	0.0397 (12)	−0.0056 (13)	0.0043 (10)	0.0094 (11)
C5	0.0543 (13)	0.0722 (16)	0.0412 (11)	0.0038 (11)	0.0089 (10)	0.0023 (11)
C6	0.0452 (12)	0.0473 (11)	0.0394 (10)	−0.0008 (9)	0.0069 (9)	0.0009 (9)
C7	0.0449 (11)	0.0473 (12)	0.0421 (11)	0.0058 (9)	0.0098 (8)	−0.0009 (9)
C8	0.0484 (11)	0.0415 (11)	0.0370 (10)	0.0023 (9)	0.0078 (8)	−0.0018 (8)
C9	0.0527 (13)	0.0529 (13)	0.0428 (11)	0.0059 (10)	0.0085 (9)	−0.0026 (10)
C10	0.0494 (12)	0.0493 (12)	0.0374 (10)	0.0022 (10)	0.0092 (9)	−0.0028 (9)
C11	0.0596 (14)	0.0747 (15)	0.0396 (11)	0.0136 (12)	−0.0006 (10)	−0.0011 (11)
C12	0.0599 (14)	0.0633 (14)	0.0360 (10)	0.0072 (11)	−0.0022 (9)	0.0020 (10)
C13	0.0534 (13)	0.0513 (12)	0.0398 (10)	0.0007 (10)	−0.0027 (9)	0.0028 (9)
C14	0.0460 (12)	0.0469 (11)	0.0412 (10)	−0.0055 (9)	−0.0008 (9)	−0.0016 (9)
C15	0.0502 (12)	0.0658 (14)	0.0505 (12)	0.0030 (11)	−0.0015 (10)	0.0049 (11)
C16	0.0529 (14)	0.0815 (18)	0.0593 (14)	0.0091 (13)	0.0096 (11)	−0.0045 (13)
C17	0.0665 (15)	0.0762 (17)	0.0413 (12)	−0.0027 (13)	0.0130 (10)	−0.0016 (11)
C18	0.0770 (16)	0.0593 (14)	0.0410 (11)	0.0070 (13)	0.0004 (10)	0.0015 (10)
C19	0.0620 (14)	0.0541 (13)	0.0429 (11)	0.0086 (11)	0.0017 (10)	0.0006 (10)

O1—C1	1.381 (2)	C8—C10	1.494 (3)
O1—C9	1.393 (3)	C11—C12	1.489 (3)
O2—C9	1.203 (2)	C11—H11A	0.9700
O3—C10	1.205 (2)	C11—H11B	0.9700
O4—C10	1.333 (2)	C12—C13	1.319 (3)
O4—C11	1.447 (3)	C12—H12A	0.9300
C1—C6	1.385 (3)	C13—C14	1.480 (3)
C1—C2	1.386 (3)	C13—H13A	0.9300
C2—C3	1.375 (3)	C14—C15	1.388 (3)
C2—H2A	0.9300	C14—C19	1.398 (3)
C3—C4	1.381 (4)	C15—C16	1.379 (3)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.380 (3)	C16—C17	1.382 (3)
C4—H4A	0.9300	C16—H16A	0.9300
C5—C6	1.405 (3)	C17—C18	1.374 (4)
C5—H5A	0.9300	C17—H17A	0.9300
C6—C7	1.426 (3)	C18—C19	1.382 (3)
C7—C8	1.349 (3)	C18—H18A	0.9300
C7—H7A	0.9300	C19—H19A	0.9300
C8—C9	1.469 (3)
C1—O1—C9	123.31 (16)	O4—C10—C8	114.69 (17)
C10—O4—C11	115.52 (16)	O4—C11—C12	109.07 (18)
O1—C1—C6	120.76 (18)	O4—C11—H11A	109.9
O1—C1—C2	117.44 (19)	C12—C11—H11A	109.9
C6—C1—C2	121.8 (2)	O4—C11—H11B	109.9
C3—C2—C1	118.3 (2)	C12—C11—H11B	109.9
C3—C2—H2A	120.9	H11A—C11—H11B	108.3
C1—C2—H2A	120.9	C13—C12—C11	126.8 (2)
C2—C3—C4	121.7 (2)	C13—C12—H12A	116.6
C2—C3—H3A	119.1	C11—C12—H12A	116.6
C4—C3—H3A	119.1	C12—C13—C14	126.4 (2)
C5—C4—C3	119.6 (2)	C12—C13—H13A	116.8
C5—C4—H4A	120.2	C14—C13—H13A	116.8
C3—C4—H4A	120.2	C15—C14—C19	117.52 (19)
C4—C5—C6	120.2 (2)	C15—C14—C13	119.69 (19)
C4—C5—H5A	119.9	C19—C14—C13	122.79 (19)
C6—C5—H5A	119.9	C16—C15—C14	121.5 (2)
C1—C6—C5	118.45 (19)	C16—C15—H15A	119.2
C1—C6—C7	117.54 (18)	C14—C15—H15A	119.2
C5—C6—C7	124.00 (19)	C15—C16—C17	120.1 (2)
C8—C7—C6	122.51 (18)	C15—C16—H16A	119.9
C8—C7—H7A	118.7	C17—C16—H16A	119.9
C6—C7—H7A	118.7	C18—C17—C16	119.4 (2)
C7—C8—C9	120.19 (18)	C18—C17—H17A	120.3
C7—C8—C10	116.55 (18)	C16—C17—H17A	120.3
C9—C8—C10	123.26 (17)	C17—C18—C19	120.6 (2)
O2—C9—O1	115.64 (19)	C17—C18—H18A	119.7
O2—C9—C8	128.7 (2)	C19—C18—H18A	119.7
O1—C9—C8	115.68 (17)	C18—C19—C14	120.8 (2)
O3—C10—O4	123.20 (19)	C18—C19—H19A	119.6
O3—C10—C8	122.10 (18)	C14—C19—H19A	119.6
C9—O1—C1—C6	0.9 (3)	C7—C8—C9—O1	1.1 (3)
C9—O1—C1—C2	−179.7 (2)	C10—C8—C9—O1	−178.51 (18)
O1—C1—C2—C3	−180.0 (2)	C11—O4—C10—O3	−1.0 (3)
C6—C1—C2—C3	−0.5 (4)	C11—O4—C10—C8	177.69 (18)
C1—C2—C3—C4	0.5 (4)	C7—C8—C10—O3	−2.4 (3)
C2—C3—C4—C5	0.2 (4)	C9—C8—C10—O3	177.2 (2)
C3—C4—C5—C6	−1.0 (4)	C7—C8—C10—O4	178.87 (18)
O1—C1—C6—C5	179.21 (19)	C9—C8—C10—O4	−1.5 (3)
C2—C1—C6—C5	−0.2 (3)	C10—O4—C11—C12	−166.07 (19)
O1—C1—C6—C7	−0.2 (3)	O4—C11—C12—C13	−3.8 (3)
C2—C1—C6—C7	−179.6 (2)	C11—C12—C13—C14	−179.2 (2)
C4—C5—C6—C1	1.0 (3)	C12—C13—C14—C15	175.4 (2)
C4—C5—C6—C7	−179.7 (2)	C12—C13—C14—C19	−4.5 (3)
C1—C6—C7—C8	−0.1 (3)	C19—C14—C15—C16	−1.2 (3)
C5—C6—C7—C8	−179.4 (2)	C13—C14—C15—C16	178.8 (2)
C6—C7—C8—C9	−0.4 (3)	C14—C15—C16—C17	0.0 (4)
C6—C7—C8—C10	179.19 (19)	C15—C16—C17—C18	1.4 (4)
C1—O1—C9—O2	178.6 (2)	C16—C17—C18—C19	−1.5 (4)
C1—O1—C9—C8	−1.4 (3)	C17—C18—C19—C14	0.2 (4)
C7—C8—C9—O2	−178.9 (2)	C15—C14—C19—C18	1.1 (3)
C10—C8—C9—O2	1.5 (4)	C13—C14—C19—C18	−178.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3i	0.93	2.54	3.344 (3)	145
C7—H7A···O3i	0.93	2.46	3.292 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O3i	0.93	2.54	3.344 (3)	145
C7—H7A⋯O3i	0.93	2.46	3.292 (3)	149

Symmetry code: (i) .