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

The title compound, C(11)H(8)O(4), features an almost planar mol-ecule (r.m.s. deviation = 0.033 Å for all non-H atoms). In the crystal, the mol-ecules are linked via C-H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to (1-21).

Related literature

For details of the biological activity of coumarins, see: Surya et al. (2006 ▶); Kostova (2006 ▶); Reddy et al. (2002 ▶); Lacy & O’Kennedy (2004 ▶). For other applications of coumarins, see: Flašík et al. (2009 ▶); Fonsecaa et al. (2010 ▶).

Experimental

Crystal data

C11H8O4

M = 204.17

Triclinic,

a = 3.8874 (10) Å

b = 9.782 (3) Å

c = 13.078 (3) Å

α = 111.569 (19)°

β = 90.83 (2)°

γ = 95.01 (2)°

V = 460.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.30 × 0.27 × 0.20 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (X-RED32; Stoe & Cie, 2001 ▶) T min = 0.967, T max = 0.978

4851 measured reflections

1725 independent reflections

1378 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.09

1725 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812040044/su2501sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040044/su2501Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812040044/su2501Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812040044/su2501Isup4.cml

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

C11H8O4	Z = 2
Mr = 204.17	F(000) = 212
Triclinic, P1	Dx = 1.474 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8874 (10) Å	Cell parameters from 10306 reflections
b = 9.782 (3) Å	θ = 3.3–26.0°
c = 13.078 (3) Å	µ = 0.11 mm−1
α = 111.569 (19)°	T = 173 K
β = 90.83 (2)°	Block, colourless
γ = 95.01 (2)°	0.30 × 0.27 × 0.20 mm
V = 460.1 (2) Å3

Stoe IPDS II two-circle diffractometer	1725 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	1378 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.054
ω scans	θmax = 25.7°, θmin = 4.2°
Absorption correction: multi-scan (X-RED32; Stoe & Cie, 2001)	h = −4→4
Tmin = 0.967, Tmax = 0.978	k = −11→11
4851 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.0733P] where P = (Fo2 + 2Fc2)/3
1725 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. Spectroscopic data for the title compound: IR (KBr, cm-1) 1710 (C═O, coumarin), 1670 (C═O), 1750 (C═O, ester), 1200 (C—O); 1HNMR (DMSO-d6, 300MHz, δ p.p.m.): 7.5 (4H, m, Ar—H), 8.1 (1H, s, Ar—H, H-4), 1.83 (3H, t, CH3), 3.20 (2H, q, CH2). Mass m/z (%): 216 M+.

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	0.8969 (3)	0.56201 (13)	0.15727 (9)	0.0371 (3)
O2	1.2039 (3)	0.76399 (14)	0.26510 (10)	0.0472 (4)
O3	0.8489 (3)	0.68616 (13)	0.54600 (9)	0.0469 (4)
O4	1.1674 (3)	0.84024 (13)	0.48731 (9)	0.0394 (3)
C1	1.0100 (4)	0.66021 (18)	0.26166 (14)	0.0352 (4)
C2	0.8796 (4)	0.62198 (18)	0.35402 (13)	0.0328 (4)
C3	0.6775 (4)	0.49482 (18)	0.33393 (13)	0.0329 (4)
H3	0.5978	0.4715	0.3945	0.039*
C4	0.5793 (4)	0.39425 (18)	0.22513 (13)	0.0330 (4)
C5	0.3781 (4)	0.25926 (18)	0.20103 (14)	0.0371 (4)
H5	0.2943	0.2314	0.2591	0.045*
C6	0.3016 (4)	0.1670 (2)	0.09335 (15)	0.0408 (4)
H6	0.1695	0.0745	0.0773	0.049*
C7	0.4178 (4)	0.2090 (2)	0.00751 (14)	0.0422 (4)
H7	0.3604	0.1452	−0.0666	0.051*
C8	0.6144 (4)	0.34155 (19)	0.02878 (14)	0.0385 (4)
H8	0.6927	0.3700	−0.0296	0.046*
C9	0.6949 (4)	0.43218 (18)	0.13747 (13)	0.0338 (4)
C10	0.9625 (4)	0.71847 (18)	0.47158 (13)	0.0338 (4)
C11	1.2460 (4)	0.9364 (2)	0.60135 (14)	0.0415 (4)
H11A	1.3986	1.0231	0.6043	0.062*
H11B	1.3614	0.8827	0.6399	0.062*
H11C	1.0311	0.9682	0.6368	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.0401 (6)	0.0439 (7)	0.0297 (6)	−0.0047 (5)	0.0051 (5)	0.0184 (5)
O2	0.0525 (7)	0.0500 (7)	0.0411 (7)	−0.0127 (6)	0.0077 (6)	0.0228 (6)
O3	0.0582 (7)	0.0504 (8)	0.0306 (7)	−0.0130 (6)	0.0077 (5)	0.0171 (6)
O4	0.0420 (6)	0.0437 (7)	0.0321 (6)	−0.0096 (5)	−0.0006 (5)	0.0167 (5)
C1	0.0333 (8)	0.0419 (9)	0.0325 (9)	−0.0004 (7)	0.0049 (6)	0.0171 (7)
C2	0.0294 (7)	0.0411 (9)	0.0312 (9)	0.0011 (6)	0.0042 (6)	0.0178 (7)
C3	0.0309 (8)	0.0423 (9)	0.0301 (8)	0.0021 (7)	0.0053 (6)	0.0191 (7)
C4	0.0304 (7)	0.0400 (9)	0.0313 (9)	0.0015 (6)	0.0033 (6)	0.0165 (7)
C5	0.0349 (8)	0.0450 (9)	0.0348 (9)	−0.0009 (7)	0.0024 (7)	0.0198 (8)
C6	0.0395 (8)	0.0422 (9)	0.0401 (10)	−0.0031 (7)	−0.0016 (7)	0.0161 (8)
C7	0.0407 (9)	0.0506 (10)	0.0318 (9)	0.0017 (8)	−0.0016 (7)	0.0120 (8)
C8	0.0372 (8)	0.0505 (10)	0.0318 (9)	0.0043 (7)	0.0044 (7)	0.0199 (8)
C9	0.0300 (7)	0.0407 (9)	0.0339 (9)	0.0018 (6)	0.0034 (6)	0.0179 (7)
C10	0.0319 (8)	0.0390 (9)	0.0333 (9)	−0.0003 (6)	0.0032 (6)	0.0173 (7)
C11	0.0417 (9)	0.0456 (10)	0.0356 (9)	−0.0061 (7)	−0.0029 (7)	0.0158 (8)

O1—C9	1.3691 (19)	C4—C5	1.400 (2)
O1—C1	1.387 (2)	C5—C6	1.376 (2)
O2—C1	1.1970 (19)	C5—H5	0.9500
O3—C10	1.2069 (19)	C6—C7	1.398 (3)
O4—C10	1.3209 (19)	C6—H6	0.9500
O4—C11	1.452 (2)	C7—C8	1.378 (2)
C1—C2	1.474 (2)	C7—H7	0.9500
C2—C3	1.348 (2)	C8—C9	1.384 (2)
C2—C10	1.491 (2)	C8—H8	0.9500
C3—C4	1.424 (2)	C11—H11A	0.9800
C3—H3	0.9500	C11—H11B	0.9800
C4—C9	1.397 (2)	C11—H11C	0.9800
C9—O1—C1	123.86 (12)	C7—C6—H6	119.9
C10—O4—C11	115.67 (12)	C8—C7—C6	120.97 (17)
O2—C1—O1	115.90 (14)	C8—C7—H7	119.5
O2—C1—C2	128.38 (16)	C6—C7—H7	119.5
O1—C1—C2	115.71 (14)	C7—C8—C9	118.30 (15)
C3—C2—C1	120.00 (16)	C7—C8—H8	120.9
C3—C2—C10	117.20 (14)	C9—C8—H8	120.9
C1—C2—C10	122.80 (15)	O1—C9—C8	117.63 (13)
C2—C3—C4	122.29 (14)	O1—C9—C4	120.23 (15)
C2—C3—H3	118.9	C8—C9—C4	122.14 (15)
C4—C3—H3	118.9	O3—C10—O4	123.18 (16)
C9—C4—C5	118.29 (15)	O3—C10—C2	121.75 (15)
C9—C4—C3	117.80 (15)	O4—C10—C2	115.07 (13)
C5—C4—C3	123.90 (14)	O4—C11—H11A	109.5
C6—C5—C4	120.13 (15)	O4—C11—H11B	109.5
C6—C5—H5	119.9	H11A—C11—H11B	109.5
C4—C5—H5	119.9	O4—C11—H11C	109.5
C5—C6—C7	120.15 (16)	H11A—C11—H11C	109.5
C5—C6—H6	119.9	H11B—C11—H11C	109.5
C9—O1—C1—O2	175.14 (13)	C1—O1—C9—C8	−177.09 (13)
C9—O1—C1—C2	−4.0 (2)	C1—O1—C9—C4	2.4 (2)
O2—C1—C2—C3	−175.95 (16)	C7—C8—C9—O1	178.57 (13)
O1—C1—C2—C3	3.1 (2)	C7—C8—C9—C4	−0.9 (2)
O2—C1—C2—C10	3.8 (3)	C5—C4—C9—O1	−178.95 (13)
O1—C1—C2—C10	−177.24 (12)	C3—C4—C9—O1	0.3 (2)
C1—C2—C3—C4	−0.7 (2)	C5—C4—C9—C8	0.6 (2)
C10—C2—C3—C4	179.63 (13)	C3—C4—C9—C8	179.76 (13)
C2—C3—C4—C9	−1.1 (2)	C11—O4—C10—O3	−0.9 (2)
C2—C3—C4—C5	178.10 (14)	C11—O4—C10—C2	179.09 (12)
C9—C4—C5—C6	0.7 (2)	C3—C2—C10—O3	−1.4 (2)
C3—C4—C5—C6	−178.50 (14)	C1—C2—C10—O3	178.88 (14)
C4—C5—C6—C7	−1.4 (2)	C3—C2—C10—O4	178.57 (13)
C5—C6—C7—C8	1.0 (2)	C1—C2—C10—O4	−1.1 (2)
C6—C7—C8—C9	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.95	2.54	3.360 (2)	145
C5—H5···O3i	0.95	2.46	3.298 (2)	147
C8—H8···O1ii	0.95	2.55	3.454 (2)	160
C11—H11A···O2iii	0.98	2.53	3.354 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.95	2.54	3.360 (2)	145
C5—H5⋯O3i	0.95	2.46	3.298 (2)	147
C8—H8⋯O1ii	0.95	2.55	3.454 (2)	160
C11—H11A⋯O2iii	0.98	2.53	3.354 (2)	142

Symmetry codes: (i) ; (ii) ; (iii) .