2-Oxo-2H-chromen-4-yl propionate.

In the title compound, C12H10O4, the atoms of the 2-oxo-2H-chromene ring system and the non-H atoms of the 4-substituent all lie on a crystallographic mirror plane. The mol-ecular structure exhibits an intra-molecular C-H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, mol-ecules form R 3 (2)(12) trimeric units via C-H⋯O inter-actions which propagate into layers parallel to the ac plane. These layers are linked by weak C-H⋯O inter-actions along the [010] direction, generating a three-dimensional network.

Related literature

For the biological activity of coumarin derivatives, see: Abernethy (1969 ▶); Wang et al. (2001 ▶); Yu et al. (2003 ▶, 2007 ▶); Vukovic et al. (2010 ▶). For industrial applications, see: O’Kennedy & Thornes (1997 ▶); Lakshmi et al. (1995 ▶). For a related structure, see: Abou et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For thermal motion of carbonyl group oxygen atoms, see: Braga & Koetzle (1988 ▶).

Experimental

Crystal data

C12H10O4

M = 218.20

Orthorhombic,

a = 9.2834 (3) Å

b = 6.7081 (2) Å

c = 16.8068 (6) Å

V = 1046.63 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.40 × 0.40 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

8092 measured reflections

1431 independent reflections

1155 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.146

S = 1.06

1431 reflections

98 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.16 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016358/zq2203sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016358/zq2203Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016358/zq2203Isup3.cml

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

C12H10O4	Dx = 1.385 Mg m−3
Mr = 218.20	Melting point = 358–359 K
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 8092 reflections
a = 9.2834 (3) Å	θ = 3.3–29.0°
b = 6.7081 (2) Å	µ = 0.11 mm−1
c = 16.8068 (6) Å	T = 298 K
V = 1046.63 (6) Å3	Parallelepiped, colourless
Z = 4	0.40 × 0.40 × 0.20 mm
F(000) = 456

Nonius KappaCCD diffractometer	1155 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 29.0°, θmin = 3.3°
φ and ω scans	h = −12→12
8092 measured reflections	k = −8→8
1431 independent reflections	l = −22→22

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.3235P] where P = (Fo2 + 2Fc2)/3
1431 reflections	(Δ/σ)max < 0.001
98 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.16 e Å−3
88 constraints

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.The DENZO image processing package used during process data may have problems with certain strong reflections. These reflections are often excluded from the data set to result in _diffrn_measured_fraction_theta_full Low (0.974 in our nvestigation study). However, it presents no problem in the refinement since the data-to-parameter ratio is superior to 10.In the initial refinement, extinction correction (EXTI) has been applied because SHELXL has suggested it; but in the last cycles of the refinement, the EXTI instruction has been removed because of PLATON checkCIF reports mentioning extinction parameter within range (2.20 σ).The non H atoms lie in the miror plane at y = 1/4. Therefore the Uij constraints (U12 = U23 = 0) generated automatically by SHELXL for this special positions (x, 1/4, z) in the space group Pnma is responsible for the elongated thermal ellipsoids in the [010] direction causing a large U3/U1 ratio for the average U(i,j) tensor (2.4).The low Ueq as compared to neighbors for atom C10 may be caused by the carbonyl bond in which the oxygen atom vibrates more than the carbon atom (Braga & Koetzle, 1988). Moreover, the decrease of Ueq from C12 to C10 of the propanoate substituent originates from the minor unresolved disordered H atoms bonded to the non disordered carbon atom C12 (split H atoms) revealed by manual inspection of PLATON (Spek, 2009) may partly justify this low Ueq of C10.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O3	0.06438 (15)	0.2500	0.59531 (8)	0.0595 (5)
O1	−0.01804 (18)	0.2500	0.35401 (8)	0.0607 (5)
C4	0.1469 (2)	0.2500	0.46462 (11)	0.0434 (4)
C3	0.0233 (2)	0.2500	0.51696 (10)	0.0428 (4)
C2	−0.1113 (2)	0.2500	0.48839 (12)	0.0481 (5)
H2	−0.1890	0.2500	0.5233	0.058*
C10	−0.0290 (2)	0.2500	0.65979 (11)	0.0460 (5)
C5	0.1204 (2)	0.2500	0.38352 (12)	0.0461 (5)
O4	−0.15508 (17)	0.2500	0.65323 (9)	0.0695 (5)
C11	0.0580 (2)	0.2500	0.73405 (11)	0.0616 (7)
H11A	0.1197	0.3668	0.7343	0.074*	0.50
H11B	0.1197	0.1332	0.7343	0.074*	0.50
C9	0.2892 (2)	0.2500	0.49029 (13)	0.0633 (7)
H9	0.3096	0.2500	0.5445	0.076*
O2	−0.25262 (19)	0.2500	0.37225 (11)	0.0921 (8)
C1	−0.1362 (2)	0.2500	0.40383 (13)	0.0579 (6)
C8	0.4004 (3)	0.2500	0.43576 (16)	0.0765 (9)
H8	0.4954	0.2500	0.4532	0.092*
C12	−0.0325 (3)	0.2500	0.80905 (13)	0.0723 (8)
H12A	−0.0996	0.1412	0.8072	0.108*	0.50
H12B	−0.0842	0.3735	0.8129	0.108*	0.50
H12C	0.0290	0.2352	0.8546	0.108*	0.50
C6	0.2310 (3)	0.2500	0.32839 (13)	0.0603 (6)
H6	0.2111	0.2500	0.2742	0.072*
C7	0.3703 (3)	0.2500	0.35516 (15)	0.0687 (7)
H7	0.4457	0.2500	0.3187	0.082*

	U11	U22	U33	U12	U13	U23
O3	0.0399 (8)	0.1082 (14)	0.0304 (7)	0.000	0.0025 (5)	0.000
O1	0.0549 (9)	0.0936 (12)	0.0336 (7)	0.000	−0.0011 (6)	0.000
C4	0.0423 (10)	0.0528 (11)	0.0351 (9)	0.000	0.0050 (7)	0.000
C3	0.0420 (10)	0.0554 (11)	0.0311 (8)	0.000	0.0007 (7)	0.000
C2	0.0401 (10)	0.0665 (13)	0.0376 (9)	0.000	0.0013 (7)	0.000
C10	0.0409 (10)	0.0616 (12)	0.0354 (9)	0.000	0.0062 (7)	0.000
C5	0.0485 (11)	0.0532 (11)	0.0368 (9)	0.000	0.0036 (8)	0.000
O4	0.0419 (8)	0.1227 (16)	0.0439 (8)	0.000	0.0053 (6)	0.000
C11	0.0468 (12)	0.1050 (19)	0.0331 (10)	0.000	0.0013 (8)	0.000
C9	0.0432 (11)	0.104 (2)	0.0432 (10)	0.000	0.0039 (9)	0.000
O2	0.0540 (10)	0.173 (2)	0.0496 (9)	0.000	−0.0147 (8)	0.000
C1	0.0493 (12)	0.0841 (16)	0.0402 (10)	0.000	−0.0031 (9)	0.000
C8	0.0440 (12)	0.126 (3)	0.0589 (15)	0.000	0.0111 (10)	0.000
C12	0.0577 (14)	0.123 (2)	0.0363 (10)	0.000	0.0053 (9)	0.000
C6	0.0654 (14)	0.0757 (16)	0.0397 (10)	0.000	0.0133 (10)	0.000
C7	0.0603 (14)	0.0908 (18)	0.0550 (13)	0.000	0.0232 (11)	0.000

O3—C3	1.371 (2)	C11—H11A	0.9700
O3—C10	1.388 (2)	C11—H11B	0.9700
O1—C5	1.378 (3)	C9—C8	1.380 (3)
O1—C1	1.380 (3)	C9—H9	0.9300
C4—C5	1.385 (3)	O2—C1	1.204 (3)
C4—C9	1.390 (3)	C8—C7	1.383 (4)
C4—C3	1.446 (3)	C8—H8	0.9300
C3—C2	1.339 (3)	C12—H12A	0.9600
C2—C1	1.440 (3)	C12—H12B	0.9600
C2—H2	0.9300	C12—H12C	0.9600
C10—O4	1.176 (3)	C6—C7	1.370 (4)
C10—C11	1.487 (3)	C6—H6	0.9300
C5—C6	1.383 (3)	C7—H7	0.9300
C11—C12	1.515 (3)
C3—O3—C10	125.20 (15)	C12—C11—H11A	108.9
C5—O1—C1	121.52 (16)	C10—C11—H11B	108.9
C5—C4—C9	118.32 (18)	C12—C11—H11B	108.9
C5—C4—C3	117.24 (17)	H11A—C11—H11B	107.7
C9—C4—C3	124.44 (18)	C8—C9—C4	120.3 (2)
C2—C3—O3	127.17 (17)	C8—C9—H9	119.9
C2—C3—C4	121.50 (17)	C4—C9—H9	119.9
O3—C3—C4	111.33 (16)	O2—C1—O1	116.48 (19)
C3—C2—C1	120.26 (18)	O2—C1—C2	125.4 (2)
C3—C2—H2	119.9	O1—C1—C2	118.13 (18)
C1—C2—H2	119.9	C9—C8—C7	120.0 (2)
O4—C10—O3	123.27 (18)	C9—C8—H8	120.0
O4—C10—C11	128.30 (18)	C7—C8—H8	120.0
O3—C10—C11	108.43 (16)	C7—C6—C5	118.8 (2)
O1—C5—C6	116.82 (19)	C7—C6—H6	120.6
O1—C5—C4	121.34 (18)	C5—C6—H6	120.6
C6—C5—C4	121.8 (2)	C6—C7—C8	120.8 (2)
C10—C11—C12	113.39 (19)	C6—C7—H7	119.6
C10—C11—H11A	108.9	C8—C7—H7	119.6
C10—O3—C3—C2	0.0	C3—C4—C5—C6	180.0
C10—O3—C3—C4	180.0	O4—C10—C11—C12	0.0
C5—C4—C3—C2	0.0	O3—C10—C11—C12	180.0
C9—C4—C3—C2	180.0	C5—C4—C9—C8	0.0
C5—C4—C3—O3	180.0	C3—C4—C9—C8	180.0
C9—C4—C3—O3	0.0	C5—O1—C1—O2	180.0
O3—C3—C2—C1	180.0	C5—O1—C1—C2	0.0
C4—C3—C2—C1	0.0	C3—C2—C1—O2	180.0
C3—O3—C10—O4	0.0	C3—C2—C1—O1	0.0
C3—O3—C10—C11	180.0	C4—C9—C8—C7	0.0
C1—O1—C5—C6	180.0	O1—C5—C6—C7	180.0
C1—O1—C5—C4	0.0	C4—C5—C6—C7	0.0
C9—C4—C5—O1	180.0	C5—C6—C7—C8	0.0
C3—C4—C5—O1	0.0	C9—C8—C7—C6	0.0
C9—C4—C5—C6	0.0

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4	0.93	2.21	2.800 (3)	121
C6—H6···O2i	0.93	2.48	3.376 (3)	161
C8—H8···O2ii	0.93	2.71	3.394 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4	0.93	2.21	2.800 (3)	121
C6—H6⋯O2i	0.93	2.48	3.376 (3)	161
C8—H8⋯O2ii	0.93	2.71	3.394 (3)	131

Symmetry codes: (i) ; (ii) .