8-Acetyl-4-methyl-2-oxo-2H-chromen-7-yl acetate.

In the title compound, C(14)H(12)O(5), the benzopyran-2-one ring system is approximately planar [maximum deviation = 0.018 (1) Å]; the mean plane is oriented at dihedral angles of 52.26 (11) and 72.92 (7)°, respectively, to the acetyl and acet-oxy groups. In the crystal, π-π stacking is observed between parallel benzene rings of adjacent mol-ecules, the centroid-centroid distance being 3.6774 (17) Å. Inter-molecular weak C-H⋯O hydrogen bonding, and C=O⋯C=O [O⋯C = 3.058 (3) Å] and C=O⋯π [O⋯centroid = 3.328 (2) Å] inter-actions occur in the crystal structure.

Related literature

For structures of related coumarin derivatives, see: Yang et al. (2006 ▶, 2007 ▶, 2010 ▶).

Experimental

Crystal data

C14H12O5

M = 260.24

Triclinic,

a = 8.198 (3) Å

b = 8.504 (3) Å

c = 9.644 (3) Å

α = 90.213 (4)°

β = 97.761 (4)°

γ = 111.686 (4)°

V = 618.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.30 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.969, T max = 0.989

4891 measured reflections

2292 independent reflections

1572 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.150

S = 1.07

2292 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048835/xu5385sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048835/xu5385Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048835/xu5385Isup3.cml

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

C14H12O5	Z = 2
Mr = 260.24	F(000) = 272
Triclinic, P1	Dx = 1.399 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.198 (3) Å	Cell parameters from 1283 reflections
b = 8.504 (3) Å	θ = 2.6–25.2°
c = 9.644 (3) Å	µ = 0.11 mm−1
α = 90.213 (4)°	T = 298 K
β = 97.761 (4)°	Prism, colourless
γ = 111.686 (4)°	0.30 × 0.10 × 0.10 mm
V = 618.0 (3) Å3

Bruker APEXII CCD area-detector diffractometer	2292 independent reflections
Radiation source: fine-focus sealed tube	1572 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.969, Tmax = 0.989	k = −10→10
4891 measured reflections	l = −11→11

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0824P)2 + 0.0107P] where P = (Fo2 + 2Fc2)/3
2292 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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
C1	0.3325 (3)	1.0614 (2)	0.9868 (2)	0.0430 (5)
C2	0.2915 (3)	1.0571 (3)	1.1282 (2)	0.0463 (5)
H2	0.3657	1.1427	1.1938	0.056*
C3	0.1515 (3)	0.9353 (2)	1.1690 (2)	0.0409 (5)
C4	0.0343 (2)	0.8014 (2)	1.0672 (2)	0.0354 (5)
C5	−0.1181 (3)	0.6703 (2)	1.0954 (2)	0.0408 (5)
H5	−0.1486	0.6655	1.1852	0.049*
C6	−0.2241 (3)	0.5482 (2)	0.9946 (2)	0.0419 (5)
H6	−0.3251	0.4615	1.0156	0.050*
C7	−0.1786 (2)	0.5559 (2)	0.8607 (2)	0.0368 (5)
C8	−0.0288 (2)	0.6828 (2)	0.8251 (2)	0.0349 (5)
C9	0.0747 (2)	0.8046 (2)	0.9306 (2)	0.0344 (5)
C10	0.1127 (3)	0.9338 (3)	1.3169 (2)	0.0646 (7)
H10A	0.2010	1.0299	1.3709	0.097*
H10B	0.1145	0.8314	1.3574	0.097*
H10C	−0.0023	0.9390	1.3168	0.097*
C11	0.0155 (3)	0.6857 (2)	0.6786 (2)	0.0432 (5)
C12	0.1973 (3)	0.6967 (3)	0.6594 (3)	0.0593 (7)
H12A	0.1881	0.6088	0.5925	0.089*
H12B	0.2594	0.6830	0.7475	0.089*
H12C	0.2612	0.8052	0.6259	0.089*
C13	−0.4432 (3)	0.4153 (3)	0.7065 (2)	0.0463 (5)
C14	−0.5350 (3)	0.2647 (3)	0.6076 (3)	0.0634 (7)
H14A	−0.6577	0.2494	0.5840	0.095*
H14B	−0.5263	0.1661	0.6508	0.095*
H14C	−0.4803	0.2813	0.5241	0.095*
O1	0.21819 (16)	0.93313 (16)	0.89181 (14)	0.0416 (4)
O2	0.4560 (2)	1.16541 (18)	0.94235 (18)	0.0601 (5)
O3	−0.27782 (17)	0.42394 (16)	0.76069 (15)	0.0447 (4)
O4	−0.5014 (2)	0.5178 (2)	0.73698 (19)	0.0684 (5)
O5	−0.0952 (2)	0.6742 (2)	0.57939 (17)	0.0694 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0312 (11)	0.0310 (11)	0.0618 (14)	0.0074 (9)	0.0020 (10)	0.0004 (10)
C2	0.0374 (12)	0.0396 (11)	0.0551 (14)	0.0110 (9)	−0.0060 (10)	−0.0082 (10)
C3	0.0402 (11)	0.0389 (11)	0.0420 (12)	0.0154 (9)	−0.0016 (9)	−0.0018 (9)
C4	0.0314 (10)	0.0343 (10)	0.0405 (11)	0.0132 (8)	0.0027 (8)	0.0019 (8)
C5	0.0393 (11)	0.0409 (11)	0.0417 (11)	0.0134 (9)	0.0093 (9)	0.0056 (9)
C6	0.0312 (10)	0.0360 (11)	0.0529 (13)	0.0047 (8)	0.0103 (9)	0.0043 (9)
C7	0.0292 (10)	0.0314 (10)	0.0463 (12)	0.0091 (8)	0.0000 (8)	−0.0022 (8)
C8	0.0296 (10)	0.0331 (10)	0.0421 (11)	0.0125 (8)	0.0034 (8)	0.0007 (8)
C9	0.0248 (9)	0.0308 (10)	0.0463 (12)	0.0090 (8)	0.0046 (8)	0.0050 (8)
C10	0.0727 (17)	0.0653 (16)	0.0455 (14)	0.0164 (13)	0.0016 (12)	−0.0083 (12)
C11	0.0415 (12)	0.0403 (11)	0.0456 (12)	0.0133 (9)	0.0050 (10)	−0.0001 (9)
C12	0.0539 (14)	0.0754 (16)	0.0571 (15)	0.0293 (12)	0.0221 (12)	0.0068 (12)
C13	0.0319 (11)	0.0500 (12)	0.0508 (13)	0.0092 (10)	0.0026 (9)	−0.0017 (10)
C14	0.0442 (14)	0.0689 (16)	0.0619 (16)	0.0076 (12)	−0.0036 (12)	−0.0196 (13)
O1	0.0315 (7)	0.0372 (8)	0.0489 (9)	0.0040 (6)	0.0070 (6)	0.0021 (6)
O2	0.0442 (9)	0.0414 (9)	0.0804 (12)	−0.0021 (7)	0.0141 (8)	0.0035 (8)
O3	0.0315 (8)	0.0380 (8)	0.0578 (9)	0.0075 (6)	0.0004 (6)	−0.0097 (7)
O4	0.0503 (10)	0.0742 (12)	0.0835 (13)	0.0333 (9)	−0.0093 (9)	−0.0180 (10)
O5	0.0583 (11)	0.1014 (14)	0.0466 (10)	0.0311 (10)	−0.0026 (8)	−0.0036 (9)

C1—O2	1.204 (2)	C9—O1	1.374 (2)
C1—O1	1.383 (2)	C10—H10A	0.9600
C1—C2	1.445 (3)	C10—H10B	0.9600
C2—C3	1.338 (3)	C10—H10C	0.9600
C2—H2	0.9300	C11—O5	1.203 (2)
C3—C4	1.453 (3)	C11—C12	1.495 (3)
C3—C10	1.502 (3)	C12—H12A	0.9600
C4—C5	1.394 (3)	C12—H12B	0.9600
C4—C9	1.400 (3)	C12—H12C	0.9600
C5—C6	1.369 (3)	C13—O4	1.191 (2)
C5—H5	0.9300	C13—O3	1.361 (2)
C6—C7	1.388 (3)	C13—C14	1.483 (3)
C6—H6	0.9300	C14—H14A	0.9600
C7—C8	1.388 (3)	C14—H14B	0.9600
C7—O3	1.399 (2)	C14—H14C	0.9600
C8—C9	1.392 (3)	O2—C1i	3.058 (3)
C8—C11	1.504 (3)	O2—C13ii	3.101 (3)
O2—C1—O1	116.15 (19)	C3—C10—H10B	109.5
O2—C1—C2	126.87 (19)	H10A—C10—H10B	109.5
O1—C1—C2	116.97 (17)	C3—C10—H10C	109.5
C3—C2—C1	122.88 (19)	H10A—C10—H10C	109.5
C3—C2—H2	118.6	H10B—C10—H10C	109.5
C1—C2—H2	118.6	O5—C11—C12	121.1 (2)
C2—C3—C4	118.98 (19)	O5—C11—C8	120.33 (19)
C2—C3—C10	121.69 (19)	C12—C11—C8	118.50 (18)
C4—C3—C10	119.33 (19)	C11—C12—H12A	109.5
C5—C4—C9	117.28 (18)	C11—C12—H12B	109.5
C5—C4—C3	124.53 (18)	H12A—C12—H12B	109.5
C9—C4—C3	118.19 (18)	C11—C12—H12C	109.5
C6—C5—C4	121.83 (19)	H12A—C12—H12C	109.5
C6—C5—H5	119.1	H12B—C12—H12C	109.5
C4—C5—H5	119.1	O4—C13—O3	122.68 (19)
C5—C6—C7	118.96 (18)	O4—C13—C14	126.4 (2)
C5—C6—H6	120.5	O3—C13—C14	110.89 (18)
C7—C6—H6	120.5	C13—C14—H14A	109.5
C6—C7—C8	122.35 (18)	C13—C14—H14B	109.5
C6—C7—O3	119.13 (17)	H14A—C14—H14B	109.5
C8—C7—O3	118.30 (17)	C13—C14—H14C	109.5
C7—C8—C9	116.78 (18)	H14A—C14—H14C	109.5
C7—C8—C11	120.47 (17)	H14B—C14—H14C	109.5
C9—C8—C11	122.75 (17)	C9—O1—C1	121.70 (15)
O1—C9—C8	115.92 (17)	C1—O2—C1i	88.63 (13)
O1—C9—C4	121.25 (17)	C1—O2—C13ii	143.37 (15)
C8—C9—C4	122.81 (18)	C1i—O2—C13ii	118.73 (8)
C3—C10—H10A	109.5	C13—O3—C7	117.16 (14)
O2—C1—C2—C3	−179.5 (2)	C3—C4—C9—O1	−1.9 (3)
O1—C1—C2—C3	0.7 (3)	C5—C4—C9—C8	−0.8 (3)
C1—C2—C3—C4	−0.3 (3)	C3—C4—C9—C8	−179.87 (16)
C1—C2—C3—C10	179.75 (19)	C7—C8—C11—O5	50.4 (3)
C2—C3—C4—C5	−178.21 (18)	C9—C8—C11—O5	−129.3 (2)
C10—C3—C4—C5	1.7 (3)	C7—C8—C11—C12	−127.4 (2)
C2—C3—C4—C9	0.8 (3)	C9—C8—C11—C12	52.9 (3)
C10—C3—C4—C9	−179.22 (18)	C8—C9—O1—C1	−179.47 (15)
C9—C4—C5—C6	0.5 (3)	C4—C9—O1—C1	2.4 (3)
C3—C4—C5—C6	179.52 (17)	O2—C1—O1—C9	178.42 (16)
C4—C5—C6—C7	−0.2 (3)	C2—C1—O1—C9	−1.7 (3)
C5—C6—C7—C8	0.2 (3)	O1—C1—O2—C1i	−87.95 (16)
C5—C6—C7—O3	174.65 (16)	C2—C1—O2—C1i	92.2 (2)
C6—C7—C8—C9	−0.4 (3)	O1—C1—O2—C13ii	52.7 (3)
O3—C7—C8—C9	−174.95 (15)	C2—C1—O2—C13ii	−127.1 (2)
C6—C7—C8—C11	179.84 (18)	O4—C13—O3—C7	2.9 (3)
O3—C7—C8—C11	5.3 (3)	C14—C13—O3—C7	−177.22 (18)
C7—C8—C9—O1	−177.37 (14)	C6—C7—O3—C13	73.3 (2)
C11—C8—C9—O1	2.3 (3)	C8—C7—O3—C13	−112.06 (19)
C7—C8—C9—C4	0.7 (3)	C1—O2—C13ii—O4ii	69.0 (3)
C11—C8—C9—C4	−179.55 (17)	C1—O2—C1i—O2i	0.0
C5—C4—C9—O1	177.26 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2iii	0.93	2.52	3.324 (3)	145.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.93	2.52	3.324 (3)	145

Symmetry code: (i) .