6-Meth-oxy-4-methyl-2H-chromen-2-one.

The whole mol-ecule of the title coumarin derivative, C(11)H(10)O(3), is approximately planar, with a maximum deviation of 0.116 (3) Å from the least-squares plane defined by all non-H atoms. In the crystal, adjacent mol-ecules are linked into chains along [011] via inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background to and applications of the title coumarin derivative, see: Grimm & Girard (2006 ▶); Maresca et al. (2010 ▶); Parvez & Hadda (2010 ▶); Raj & Wenge (1998 ▶); Yao & Deng (2000 ▶). For related coumarin structures, see: Asad et al. (2010 ▶); Saidi et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H10O3

M = 190.19

Triclinic,

a = 7.2554 (2) Å

b = 8.0880 (2) Å

c = 8.5450 (2) Å

α = 112.988 (1)°

β = 90.234 (1)°

γ = 93.873 (1)°

V = 460.31 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.40 × 0.35 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.962, T max = 0.994

10271 measured reflections

2793 independent reflections

1675 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.218

S = 1.09

2793 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.20 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051652/is2642sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051652/is2642Isup2.hkl

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

C11H10O3	Z = 2
Mr = 190.19	F(000) = 200
Triclinic, P1	Dx = 1.372 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2554 (2) Å	Cell parameters from 3241 reflections
b = 8.0880 (2) Å	θ = 2.6–30.0°
c = 8.5450 (2) Å	µ = 0.10 mm−1
α = 112.988 (1)°	T = 293 K
β = 90.234 (1)°	Plate, yellow
γ = 93.873 (1)°	0.40 × 0.35 × 0.06 mm
V = 460.31 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2793 independent reflections
Radiation source: fine-focus sealed tube	1675 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 30.6°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.962, Tmax = 0.994	k = −11→11
10271 measured reflections	l = −11→12

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0991P)2 + 0.086P] where P = (Fo2 + 2Fc2)/3
2793 reflections	(Δ/σ)max < 0.001
129 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.20 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
O1	0.19469 (16)	0.53037 (17)	0.87871 (16)	0.0508 (4)
O2	0.6197 (2)	1.09931 (18)	1.34611 (17)	0.0638 (4)
O3	0.1468 (2)	0.2933 (2)	0.63843 (19)	0.0679 (5)
C1	0.3087 (2)	0.6718 (2)	0.9894 (2)	0.0417 (4)
C2	0.2327 (3)	0.7819 (3)	1.1396 (2)	0.0512 (5)
H2A	0.1101	0.7603	1.1617	0.061*
C3	0.3402 (3)	0.9229 (3)	1.2551 (2)	0.0527 (5)
H3A	0.2901	0.9974	1.3559	0.063*
C4	0.5250 (3)	0.9555 (2)	1.2222 (2)	0.0472 (4)
C5	0.5999 (2)	0.8469 (2)	1.0726 (2)	0.0438 (4)
H5A	0.7225	0.8696	1.0510	0.053*
C6	0.4917 (2)	0.7016 (2)	0.9521 (2)	0.0384 (4)
C7	0.5603 (2)	0.5807 (2)	0.7919 (2)	0.0414 (4)
C8	0.4450 (2)	0.4441 (2)	0.6875 (2)	0.0463 (4)
H8A	0.4895	0.3663	0.5851	0.056*
C9	0.2564 (3)	0.4127 (2)	0.7264 (2)	0.0475 (4)
C10	0.8119 (3)	1.1270 (3)	1.3272 (3)	0.0695 (6)
H10C	0.8624	1.2287	1.4242	0.104*
H10D	0.8317	1.1495	1.2260	0.104*
H10A	0.8718	1.0217	1.3187	0.104*
C11	0.7558 (3)	0.6091 (3)	0.7459 (3)	0.0573 (5)
H11D	0.7824	0.5119	0.6419	0.086*
H11A	0.8387	0.6128	0.8352	0.086*
H11B	0.7713	0.7209	0.7311	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0352 (6)	0.0577 (8)	0.0514 (8)	0.0001 (5)	0.0021 (5)	0.0132 (6)
O2	0.0694 (10)	0.0531 (8)	0.0488 (8)	0.0036 (7)	−0.0011 (7)	−0.0017 (6)
O3	0.0523 (8)	0.0717 (9)	0.0622 (9)	−0.0130 (7)	−0.0092 (7)	0.0103 (8)
C1	0.0368 (8)	0.0467 (9)	0.0413 (9)	0.0056 (7)	0.0016 (7)	0.0164 (7)
C2	0.0411 (9)	0.0600 (11)	0.0516 (11)	0.0141 (8)	0.0130 (8)	0.0193 (9)
C3	0.0579 (11)	0.0553 (11)	0.0413 (10)	0.0187 (9)	0.0120 (8)	0.0125 (8)
C4	0.0541 (11)	0.0434 (9)	0.0394 (9)	0.0087 (8)	−0.0003 (8)	0.0104 (7)
C5	0.0400 (9)	0.0467 (9)	0.0416 (9)	0.0039 (7)	0.0031 (7)	0.0139 (7)
C6	0.0362 (8)	0.0418 (8)	0.0367 (8)	0.0073 (6)	0.0023 (6)	0.0141 (7)
C7	0.0384 (9)	0.0457 (9)	0.0387 (9)	0.0068 (7)	0.0042 (7)	0.0145 (7)
C8	0.0461 (10)	0.0480 (9)	0.0388 (9)	0.0059 (7)	0.0031 (7)	0.0102 (7)
C9	0.0429 (9)	0.0511 (10)	0.0440 (10)	0.0006 (8)	−0.0033 (7)	0.0144 (8)
C10	0.0654 (14)	0.0596 (12)	0.0646 (14)	−0.0073 (10)	−0.0111 (11)	0.0060 (10)
C11	0.0466 (10)	0.0633 (12)	0.0508 (11)	0.0045 (9)	0.0119 (8)	0.0100 (9)

O1—C9	1.377 (2)	C5—H5A	0.9300
O1—C1	1.381 (2)	C6—C7	1.450 (2)
O2—C4	1.367 (2)	C7—C8	1.348 (2)
O2—C10	1.417 (3)	C7—C11	1.500 (2)
O3—C9	1.206 (2)	C8—C9	1.438 (3)
C1—C2	1.387 (2)	C8—H8A	0.9300
C1—C6	1.394 (2)	C10—H10C	0.9600
C2—C3	1.370 (3)	C10—H10D	0.9600
C2—H2A	0.9300	C10—H10A	0.9600
C3—C4	1.400 (3)	C11—H11D	0.9600
C3—H3A	0.9300	C11—H11A	0.9600
C4—C5	1.376 (2)	C11—H11B	0.9600
C5—C6	1.407 (2)
C9—O1—C1	121.54 (14)	C8—C7—C11	121.52 (15)
C4—O2—C10	117.77 (15)	C6—C7—C11	119.97 (15)
O1—C1—C2	116.85 (15)	C7—C8—C9	123.28 (16)
O1—C1—C6	121.51 (15)	C7—C8—H8A	118.4
C2—C1—C6	121.65 (16)	C9—C8—H8A	118.4
C3—C2—C1	119.36 (17)	O3—C9—O1	116.69 (17)
C3—C2—H2A	120.3	O3—C9—C8	126.37 (18)
C1—C2—H2A	120.3	O1—C9—C8	116.95 (15)
C2—C3—C4	120.41 (16)	O2—C10—H10C	109.5
C2—C3—H3A	119.8	O2—C10—H10D	109.5
C4—C3—H3A	119.8	H10C—C10—H10D	109.5
O2—C4—C5	124.24 (17)	O2—C10—H10A	109.5
O2—C4—C3	115.58 (16)	H10C—C10—H10A	109.5
C5—C4—C3	120.18 (17)	H10D—C10—H10A	109.5
C4—C5—C6	120.30 (16)	C7—C11—H11D	109.5
C4—C5—H5A	119.8	C7—C11—H11A	109.5
C6—C5—H5A	119.8	H11D—C11—H11A	109.5
C1—C6—C5	118.10 (15)	C7—C11—H11B	109.5
C1—C6—C7	118.22 (15)	H11D—C11—H11B	109.5
C5—C6—C7	123.68 (15)	H11A—C11—H11B	109.5
C8—C7—C6	118.51 (15)
C9—O1—C1—C2	−179.81 (14)	C2—C1—C6—C7	−179.76 (15)
C9—O1—C1—C6	−0.2 (3)	C4—C5—C6—C1	−0.1 (3)
O1—C1—C2—C3	179.14 (15)	C4—C5—C6—C7	−179.79 (14)
C6—C1—C2—C3	−0.4 (3)	C1—C6—C7—C8	−0.8 (2)
C1—C2—C3—C4	−0.1 (3)	C5—C6—C7—C8	178.89 (15)
C10—O2—C4—C5	−6.8 (3)	C1—C6—C7—C11	179.31 (16)
C10—O2—C4—C3	173.65 (17)	C5—C6—C7—C11	−1.0 (3)
C2—C3—C4—O2	−179.84 (16)	C6—C7—C8—C9	0.4 (3)
C2—C3—C4—C5	0.6 (3)	C11—C7—C8—C9	−179.67 (17)
O2—C4—C5—C6	−179.97 (15)	C1—O1—C9—O3	179.91 (15)
C3—C4—C5—C6	−0.4 (3)	C1—O1—C9—C8	−0.2 (3)
O1—C1—C6—C5	−178.98 (14)	C7—C8—C9—O3	179.99 (18)
C2—C1—C6—C5	0.6 (3)	C7—C8—C9—O1	0.1 (3)
O1—C1—C6—C7	0.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2i	0.93	2.56	3.471 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2i	0.93	2.56	3.471 (2)	165

Symmetry code: (i) .