Crystal structure of methyl 2-(7-hy-droxy-2-oxo-2H-chromen-4-yl)acetate.

In the title coumarin derivative, C12H10O5, the fused ring system is almost planar (r.m.s deviation = 0.016 Å). The Car-C-C=O torsion angle of the side chain is -8.4 (2)° In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, generating C(8) chains propagating in the [100] direction. The chains are cross-linked by weak C-H⋯O inter-actions, thereby generating undulating (001) sheets.

Related literature

For the applications and biological activities of coumarin derivatives, see: Vukovic et al. (2010 ▸); Basanagouda et al. (2009 ▸); Ahmad et al. (2008 ▸); Abd Elhafez et al. (2003 ▸); Ukhov et al. (2001 ▸); Emmanuel-Giota et al. (2001 ▸). For the crystal structure of a related compound, see: Subramanian et al. (1990 ▸).

Experimental

Crystal data

C12H10O5

M = 234.20

Orthorhombic,

a = 13.0780 (12) Å

b = 7.2354 (7) Å

c = 22.262 (2) Å

V = 2106.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 273 K

0.62 × 0.35 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▸) T min = 0.932, T max = 0.992

11536 measured reflections

1958 independent reflections

1669 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.104

S = 1.03

1958 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 ▸); cell refinement: SAINT (Bruker, 2000 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015014061/hb7469sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014061/hb7469Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015014061/hb7469Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015014061/hb7469fig1.tif

The mol­ecular structure of (I) with displacement ellipsoids drawn at 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015014061/hb7469fig2.tif

The crystal packing of the title compound I. Only hydrogen atoms involved in hydrogen bonding are shown.

CCDC reference: 1415274

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H10O5	Dx = 1.477 Mg m−3
Mr = 234.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4477 reflections
a = 13.0780 (12) Å	θ = 2.4–28.3°
b = 7.2354 (7) Å	µ = 0.12 mm−1
c = 22.262 (2) Å	T = 273 K
V = 2106.5 (3) Å3	Plate, yellow
Z = 8	0.62 × 0.35 × 0.07 mm
F(000) = 976

Bruker SMART APEX CCD diffractometer	1958 independent reflections
Radiation source: fine-focus sealed tube	1669 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scan	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→14
Tmin = 0.932, Tmax = 0.992	k = −8→8
11536 measured reflections	l = −26→26

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0523P)2 + 0.6817P] where P = (Fo2 + 2Fc2)/3
1958 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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	0.42044 (8)	0.1647 (2)	0.43882 (5)	0.0591 (4)
O2	0.58807 (7)	0.16062 (15)	0.44081 (4)	0.0403 (3)
O3	0.94960 (9)	0.1761 (2)	0.45283 (6)	0.0597 (4)
O4	0.64831 (11)	0.23456 (17)	0.22259 (5)	0.0633 (4)
O5	0.64257 (9)	−0.01095 (16)	0.16271 (5)	0.0525 (3)
C1	0.50365 (12)	0.0564 (2)	0.35141 (6)	0.0440 (4)
H1A	0.4432	0.0350	0.3305	0.053*
C2	0.49845 (11)	0.1288 (2)	0.41145 (7)	0.0432 (4)
C3	0.68119 (11)	0.12502 (18)	0.41444 (6)	0.0338 (3)
C4	0.76625 (11)	0.1663 (2)	0.44865 (6)	0.0365 (3)
H4A	0.7595	0.2141	0.4872	0.044*
C5	0.86154 (11)	0.1347 (2)	0.42403 (6)	0.0397 (4)
C6	0.87047 (12)	0.0581 (2)	0.36677 (7)	0.0414 (4)
H6A	0.9349	0.0341	0.3509	0.050*
C7	0.78507 (11)	0.01819 (19)	0.33383 (6)	0.0376 (3)
H7A	0.7923	−0.0328	0.2957	0.045*
C8	0.68705 (11)	0.05257 (18)	0.35637 (6)	0.0336 (3)
C9	0.59328 (12)	0.01865 (19)	0.32448 (6)	0.0375 (3)
C10	0.59598 (12)	−0.0602 (2)	0.26187 (6)	0.0426 (4)
H10A	0.6403	−0.1677	0.2617	0.051*
H10B	0.5278	−0.1013	0.2512	0.051*
C11	0.63285 (11)	0.0736 (2)	0.21485 (6)	0.0379 (3)
C12	0.67778 (15)	0.1002 (3)	0.11240 (8)	0.0640 (5)
H12A	0.6822	0.0244	0.0771	0.096*
H12B	0.7440	0.1503	0.1214	0.096*
H12C	0.6304	0.1993	0.1054	0.096*
H3	0.9369 (17)	0.231 (3)	0.4915 (11)	0.091 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0375 (6)	0.0935 (10)	0.0463 (7)	0.0056 (6)	0.0053 (5)	−0.0091 (6)
O2	0.0358 (6)	0.0533 (6)	0.0318 (5)	0.0014 (5)	0.0024 (4)	−0.0043 (4)
O3	0.0379 (7)	0.0923 (10)	0.0489 (7)	−0.0035 (6)	−0.0062 (5)	−0.0117 (6)
O4	0.1002 (11)	0.0475 (7)	0.0424 (6)	−0.0102 (7)	−0.0047 (6)	−0.0019 (5)
O5	0.0647 (8)	0.0582 (7)	0.0345 (6)	−0.0042 (6)	0.0086 (5)	−0.0083 (5)
C1	0.0401 (9)	0.0549 (9)	0.0371 (8)	−0.0024 (7)	−0.0052 (6)	−0.0016 (7)
C2	0.0390 (8)	0.0527 (9)	0.0379 (8)	0.0009 (7)	0.0006 (6)	0.0009 (7)
C3	0.0375 (8)	0.0340 (7)	0.0298 (7)	0.0035 (6)	0.0027 (6)	0.0018 (5)
C4	0.0420 (9)	0.0400 (7)	0.0276 (6)	0.0000 (6)	−0.0010 (6)	−0.0025 (5)
C5	0.0387 (8)	0.0436 (8)	0.0368 (8)	−0.0002 (6)	−0.0041 (6)	0.0017 (6)
C6	0.0391 (8)	0.0451 (8)	0.0401 (8)	0.0053 (7)	0.0056 (6)	−0.0003 (6)
C7	0.0455 (9)	0.0360 (7)	0.0314 (7)	0.0038 (6)	0.0032 (6)	−0.0024 (6)
C8	0.0399 (8)	0.0310 (7)	0.0300 (7)	0.0009 (6)	−0.0003 (6)	−0.0001 (5)
C9	0.0451 (9)	0.0360 (7)	0.0314 (7)	−0.0023 (6)	−0.0024 (6)	0.0007 (6)
C10	0.0486 (9)	0.0446 (8)	0.0345 (8)	−0.0049 (7)	−0.0046 (6)	−0.0055 (6)
C11	0.0346 (8)	0.0464 (8)	0.0327 (7)	0.0005 (6)	−0.0059 (6)	−0.0049 (6)
C12	0.0679 (12)	0.0845 (14)	0.0394 (9)	−0.0071 (10)	0.0132 (8)	0.0016 (9)

O1—C2	1.2165 (18)	C4—H4A	0.9300
O2—C2	1.3617 (18)	C5—C6	1.395 (2)
O2—C3	1.3764 (17)	C6—C7	1.367 (2)
O3—C5	1.3515 (18)	C6—H6A	0.9300
O3—H3	0.96 (2)	C7—C8	1.399 (2)
O4—C11	1.1944 (19)	C7—H7A	0.9300
O5—C11	1.3183 (17)	C8—C9	1.438 (2)
O5—C12	1.454 (2)	C9—C10	1.5064 (19)
C1—C9	1.345 (2)	C10—C11	1.505 (2)
C1—C2	1.437 (2)	C10—H10A	0.9700
C1—H1A	0.9300	C10—H10B	0.9700
C3—C4	1.381 (2)	C12—H12A	0.9600
C3—C8	1.3971 (19)	C12—H12B	0.9600
C4—C5	1.380 (2)	C12—H12C	0.9600
C2—O2—C3	121.67 (11)	C8—C7—H7A	119.4
C5—O3—H3	111.6 (14)	C3—C8—C7	116.67 (12)
C11—O5—C12	116.88 (13)	C3—C8—C9	118.30 (13)
C9—C1—C2	122.00 (13)	C7—C8—C9	125.03 (12)
C9—C1—H1A	119.0	C1—C9—C8	119.25 (13)
C2—C1—H1A	119.0	C1—C9—C10	120.65 (13)
O1—C2—O2	116.43 (13)	C8—C9—C10	120.09 (13)
O1—C2—C1	125.70 (14)	C11—C10—C9	114.04 (12)
O2—C2—C1	117.87 (13)	C11—C10—H10A	108.7
O2—C3—C4	115.91 (12)	C9—C10—H10A	108.7
O2—C3—C8	120.90 (12)	C11—C10—H10B	108.7
C4—C3—C8	123.19 (13)	C9—C10—H10B	108.7
C5—C4—C3	118.19 (13)	H10A—C10—H10B	107.6
C5—C4—H4A	120.9	O4—C11—O5	124.29 (14)
C3—C4—H4A	120.9	O4—C11—C10	125.51 (13)
O3—C5—C4	122.97 (13)	O5—C11—C10	110.16 (13)
O3—C5—C6	116.74 (14)	O5—C12—H12A	109.5
C4—C5—C6	120.28 (13)	O5—C12—H12B	109.5
C7—C6—C5	120.38 (14)	H12A—C12—H12B	109.5
C7—C6—H6A	119.8	O5—C12—H12C	109.5
C5—C6—H6A	119.8	H12A—C12—H12C	109.5
C6—C7—C8	121.25 (13)	H12B—C12—H12C	109.5
C6—C7—H7A	119.4
C3—O2—C2—O1	179.92 (13)	C4—C3—C8—C9	−178.69 (13)
C3—O2—C2—C1	−0.1 (2)	C6—C7—C8—C3	−1.5 (2)
C9—C1—C2—O1	−179.37 (16)	C6—C7—C8—C9	178.62 (13)
C9—C1—C2—O2	0.7 (2)	C2—C1—C9—C8	−0.4 (2)
C2—O2—C3—C4	178.95 (12)	C2—C1—C9—C10	178.94 (14)
C2—O2—C3—C8	−0.7 (2)	C3—C8—C9—C1	−0.4 (2)
O2—C3—C4—C5	−179.42 (12)	C7—C8—C9—C1	179.48 (14)
C8—C3—C4—C5	0.2 (2)	C3—C8—C9—C10	−179.72 (13)
C3—C4—C5—O3	177.69 (14)	C7—C8—C9—C10	0.1 (2)
C3—C4—C5—C6	−1.8 (2)	C1—C9—C10—C11	108.63 (16)
O3—C5—C6—C7	−177.79 (14)	C8—C9—C10—C11	−72.02 (18)
C4—C5—C6—C7	1.8 (2)	C12—O5—C11—O4	2.1 (2)
C5—C6—C7—C8	0.0 (2)	C12—O5—C11—C10	−179.98 (14)
O2—C3—C8—C7	−178.95 (12)	C9—C10—C11—O4	−8.4 (2)
C4—C3—C8—C7	1.5 (2)	C9—C10—C11—O5	173.79 (13)
O2—C3—C8—C9	0.91 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1i	0.96 (2)	1.74 (2)	2.7002 (17)	177 (2)
C7—H7A···O4ii	0.93	2.47	3.3320 (18)	155

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O3H3O1i	0.96(2)	1.74(2)	2.7002(17)	177(2)
C7H7AO4ii	0.93	2.47	3.3320(18)	155

Symmetry codes: (i) ; (ii) .