Ethyl 2-[(2-oxo-2H-chromen-7-yl)-oxy]acetate.

In the title compound, C13H12O5, the mean plane of the 2H-chromene ring system (r.m.s deviation = 0.026 Å) forms a dihedral angle of 81.71 (6)° with the mean plane of ethyl 2-hy-droxy-acetate moiety (r.m.s deviation = 0.034 Å). In the crystal, C-H⋯O hydrogen bonds result in the formation of zigzag layers parallel to the bc plane.

Related literature

For general background to and the high emission quantum yield, photo stability and good solubility in common solvents of coumarin derivatives, see: Xie et al. (2012 ▶); Liu et al. (2012 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For related structures, see: Arshad et al. (2010a ▶,b ▶).

Experimental

Crystal data

C13H12O5

M = 248.23

Monoclinic,

a = 8.1435 (2) Å

b = 16.4887 (4) Å

c = 10.5506 (3) Å

β = 125.882 (2)°

V = 1147.84 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.31 × 0.24 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.966, T max = 0.988

12656 measured reflections

3344 independent reflections

2308 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.114

S = 1.04

3344 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813005539/rz5046sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005539/rz5046Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005539/rz5046Isup3.cml

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

C13H12O5	F(000) = 520
Mr = 248.23	Dx = 1.436 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3372 reflections
a = 8.1435 (2) Å	θ = 2.5–29.4°
b = 16.4887 (4) Å	µ = 0.11 mm−1
c = 10.5506 (3) Å	T = 100 K
β = 125.882 (2)°	Block, colourless
V = 1147.84 (5) Å3	0.31 × 0.24 × 0.11 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3344 independent reflections
Radiation source: fine-focus sealed tube	2308 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→11
Tmin = 0.966, Tmax = 0.988	k = −23→15
12656 measured reflections	l = −14→14

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.040P)2 + 0.4605P] where P = (Fo2 + 2Fc2)/3
3344 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 2sigma(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	0.39589 (16)	0.81519 (6)	0.17293 (12)	0.0225 (2)
O2	0.48206 (18)	0.71922 (7)	0.07680 (13)	0.0311 (3)
O3	0.23054 (17)	1.01606 (6)	0.40644 (13)	0.0273 (3)
O4	0.06112 (16)	0.85696 (7)	0.53551 (13)	0.0284 (3)
O5	−0.09962 (17)	0.91734 (7)	0.30015 (13)	0.0305 (3)
C1	0.3155 (2)	0.91211 (9)	0.29088 (17)	0.0211 (3)
H1A	0.3389	0.8732	0.3635	0.025*
C2	0.3385 (2)	0.89394 (9)	0.17359 (16)	0.0193 (3)
C3	0.4238 (2)	0.78861 (10)	0.06252 (18)	0.0246 (3)
C4	0.3788 (2)	0.84577 (10)	−0.05922 (18)	0.0268 (3)
H4A	0.3890	0.8291	−0.1386	0.032*
C5	0.3227 (2)	0.92215 (10)	−0.05837 (18)	0.0270 (3)
H5A	0.2957	0.9579	−0.1367	0.032*
C6	0.3039 (2)	0.94961 (9)	0.06176 (17)	0.0221 (3)
C7	0.2475 (2)	1.02864 (10)	0.07243 (18)	0.0254 (3)
H7A	0.2248	1.0677	0.0001	0.031*
C8	0.2255 (2)	1.04899 (9)	0.18806 (18)	0.0243 (3)
H8A	0.1900	1.1016	0.1947	0.029*
C9	0.2567 (2)	0.98993 (9)	0.29621 (17)	0.0225 (3)
C10	0.2416 (2)	0.95782 (10)	0.51046 (18)	0.0253 (3)
H10A	0.2669	0.9853	0.6017	0.030*
H10B	0.3541	0.9213	0.5454	0.030*
C11	0.0474 (2)	0.90906 (9)	0.43309 (17)	0.0232 (3)
C12	−0.1214 (2)	0.80927 (10)	0.4789 (2)	0.0301 (4)
H12A	−0.1582	0.7776	0.3882	0.036*
H12B	−0.2336	0.8449	0.4489	0.036*
C13	−0.0765 (3)	0.75434 (11)	0.6084 (2)	0.0381 (4)
H13A	−0.1945	0.7226	0.5743	0.057*
H13B	−0.0400	0.7862	0.6975	0.057*
H13C	0.0337	0.7190	0.6365	0.057*

	U11	U22	U33	U12	U13	U23
O1	0.0289 (6)	0.0198 (5)	0.0218 (5)	0.0002 (4)	0.0166 (5)	0.0001 (4)
O2	0.0396 (7)	0.0241 (6)	0.0342 (6)	−0.0001 (5)	0.0243 (6)	−0.0039 (5)
O3	0.0382 (6)	0.0211 (6)	0.0293 (6)	−0.0009 (5)	0.0236 (5)	−0.0021 (5)
O4	0.0249 (6)	0.0342 (6)	0.0231 (5)	−0.0025 (5)	0.0125 (5)	0.0046 (5)
O5	0.0309 (6)	0.0332 (7)	0.0220 (6)	0.0021 (5)	0.0125 (5)	0.0023 (5)
C1	0.0242 (7)	0.0208 (7)	0.0189 (7)	−0.0017 (6)	0.0129 (6)	0.0021 (6)
C2	0.0181 (7)	0.0183 (7)	0.0185 (7)	−0.0015 (5)	0.0091 (6)	−0.0009 (5)
C3	0.0237 (7)	0.0282 (9)	0.0227 (8)	−0.0039 (6)	0.0140 (7)	−0.0054 (6)
C4	0.0269 (8)	0.0334 (9)	0.0218 (8)	−0.0023 (7)	0.0152 (7)	−0.0011 (7)
C5	0.0268 (8)	0.0342 (9)	0.0203 (7)	−0.0013 (7)	0.0139 (7)	0.0047 (7)
C6	0.0191 (7)	0.0263 (8)	0.0183 (7)	−0.0021 (6)	0.0095 (6)	0.0021 (6)
C7	0.0237 (7)	0.0246 (8)	0.0255 (8)	−0.0001 (6)	0.0130 (7)	0.0067 (6)
C8	0.0242 (8)	0.0187 (8)	0.0285 (8)	−0.0008 (6)	0.0146 (7)	0.0006 (6)
C9	0.0232 (7)	0.0237 (8)	0.0216 (7)	−0.0036 (6)	0.0136 (6)	−0.0027 (6)
C10	0.0289 (8)	0.0270 (8)	0.0219 (7)	−0.0006 (7)	0.0160 (7)	−0.0016 (6)
C11	0.0280 (8)	0.0224 (8)	0.0213 (7)	0.0038 (6)	0.0156 (7)	0.0000 (6)
C12	0.0256 (8)	0.0314 (9)	0.0295 (8)	−0.0033 (7)	0.0142 (7)	−0.0025 (7)
C13	0.0324 (9)	0.0384 (10)	0.0474 (11)	0.0026 (8)	0.0257 (9)	0.0110 (9)

O1—C2	1.3814 (17)	C5—H5A	0.9300
O1—C3	1.3827 (17)	C6—C7	1.408 (2)
O2—C3	1.2136 (19)	C7—C8	1.375 (2)
O3—C9	1.3692 (17)	C7—H7A	0.9300
O3—C10	1.4211 (18)	C8—C9	1.405 (2)
O4—C11	1.3328 (18)	C8—H8A	0.9300
O4—C12	1.4642 (19)	C10—C11	1.516 (2)
O5—C11	1.2045 (18)	C10—H10A	0.9700
C1—C9	1.382 (2)	C10—H10B	0.9700
C1—C2	1.389 (2)	C12—C13	1.495 (2)
C1—H1A	0.9300	C12—H12A	0.9700
C2—C6	1.387 (2)	C12—H12B	0.9700
C3—C4	1.456 (2)	C13—H13A	0.9600
C4—C5	1.341 (2)	C13—H13B	0.9600
C4—H4A	0.9300	C13—H13C	0.9600
C5—C6	1.436 (2)
C2—O1—C3	121.70 (12)	C9—C8—H8A	120.1
C9—O3—C10	118.20 (12)	O3—C9—C1	123.83 (13)
C11—O4—C12	115.63 (12)	O3—C9—C8	115.29 (13)
C9—C1—C2	117.86 (13)	C1—C9—C8	120.85 (14)
C9—C1—H1A	121.1	O3—C10—C11	111.63 (12)
C2—C1—H1A	121.1	O3—C10—H10A	109.3
O1—C2—C6	121.23 (13)	C11—C10—H10A	109.3
O1—C2—C1	115.48 (12)	O3—C10—H10B	109.3
C6—C2—C1	123.28 (14)	C11—C10—H10B	109.3
O2—C3—O1	116.08 (14)	H10A—C10—H10B	108.0
O2—C3—C4	126.72 (14)	O5—C11—O4	124.81 (15)
O1—C3—C4	117.20 (14)	O5—C11—C10	125.30 (14)
C5—C4—C3	120.84 (14)	O4—C11—C10	109.86 (12)
C5—C4—H4A	119.6	O4—C12—C13	107.85 (13)
C3—C4—H4A	119.6	O4—C12—H12A	110.1
C4—C5—C6	120.98 (14)	C13—C12—H12A	110.1
C4—C5—H5A	119.5	O4—C12—H12B	110.1
C6—C5—H5A	119.5	C13—C12—H12B	110.1
C2—C6—C7	117.25 (14)	H12A—C12—H12B	108.5
C2—C6—C5	117.92 (14)	C12—C13—H13A	109.5
C7—C6—C5	124.81 (14)	C12—C13—H13B	109.5
C8—C7—C6	121.00 (14)	H13A—C13—H13B	109.5
C8—C7—H7A	119.5	C12—C13—H13C	109.5
C6—C7—H7A	119.5	H13A—C13—H13C	109.5
C7—C8—C9	119.71 (14)	H13B—C13—H13C	109.5
C7—C8—H8A	120.1
C3—O1—C2—C6	0.8 (2)	C2—C6—C7—C8	−0.8 (2)
C3—O1—C2—C1	179.82 (13)	C5—C6—C7—C8	177.46 (15)
C9—C1—C2—O1	−179.53 (12)	C6—C7—C8—C9	−0.9 (2)
C9—C1—C2—C6	−0.6 (2)	C10—O3—C9—C1	−7.5 (2)
C2—O1—C3—O2	177.16 (13)	C10—O3—C9—C8	174.34 (13)
C2—O1—C3—C4	−3.51 (19)	C2—C1—C9—O3	−179.32 (13)
O2—C3—C4—C5	−177.40 (16)	C2—C1—C9—C8	−1.3 (2)
O1—C3—C4—C5	3.4 (2)	C7—C8—C9—O3	−179.80 (13)
C3—C4—C5—C6	−0.5 (2)	C7—C8—C9—C1	2.0 (2)
O1—C2—C6—C7	−179.50 (13)	C9—O3—C10—C11	−78.32 (16)
C1—C2—C6—C7	1.6 (2)	C12—O4—C11—O5	−1.9 (2)
O1—C2—C6—C5	2.1 (2)	C12—O4—C11—C10	176.37 (12)
C1—C2—C6—C5	−176.81 (14)	O3—C10—C11—O5	0.2 (2)
C4—C5—C6—C2	−2.2 (2)	O3—C10—C11—O4	−178.06 (12)
C4—C5—C6—C7	179.51 (15)	C11—O4—C12—C13	179.49 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2i	0.93	2.38	3.2913 (19)	166
C5—H5A···O5ii	0.93	2.55	3.373 (2)	147
C10—H10B···O2i	0.97	2.48	3.353 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2i	0.93	2.38	3.2913 (19)	166
C5—H5A⋯O5ii	0.93	2.55	3.373 (2)	147
C10—H10B⋯O2i	0.97	2.48	3.353 (2)	149

Symmetry codes: (i) ; (ii) .