5-Meth-oxy-2-benzofuran-1(3H)-one.

In the title compound, C9H8O3, the mol-ecular skeleton is almost planar, with an r.m.s. deviation of 0.010 (2) Å. In the crystal, weak C-H⋯O hydrogen bonds connect the mol-ecules into a two-dimensional network parallel to the ac plane.

Related literature

For the biological activity of isobenzofuran-1(3H)-one, see: Ma et al. (2012 ▶); Huang et al. (2012 ▶); Zhao et al. (2012 ▶); Arnone et al. (2002 ▶). For the synthesis, see: Zhang et al. (2009 ▶). For related structures, see: Sun et al. (2009 ▶); Mendenhall et al. (2003 ▶); Pereira et al. (2012 ▶).

Experimental

Crystal data

C9H8O3

M = 164.15

Monoclinic,

a = 8.1819 (9) Å

b = 10.4285 (18) Å

c = 9.2965 (9) Å

β = 99.962 (8)°

V = 781.26 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.18 × 0.16 mm

Data collection

Enraf–Nonius KappaCCD diffractometer

14100 measured reflections

1587 independent reflections

1101 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.147

S = 1.06

1587 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.13 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044789/zs2239sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044789/zs2239Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044789/zs2239Isup3.cml

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

C9H8O3	Dx = 1.396 Mg m−3
Mr = 164.15	Melting point = 386.4–386.7 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.1819 (9) Å	Cell parameters from 1685 reflections
b = 10.4285 (18) Å	θ = 3.2–26.4°
c = 9.2965 (9) Å	µ = 0.11 mm−1
β = 99.962 (8)°	T = 293 K
V = 781.26 (18) Å3	Prism, yellow
Z = 4	0.30 × 0.18 × 0.16 mm
F(000) = 344

Enraf–Nonius KappaCCD diffractometer	1101 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590 X-ray source	Rint = 0.049
Graphite monochromator	θmax = 26.4°, θmin = 3.2°
Detector resolution: 9 pixels mm-1	h = 0→10
CCD rotation images, thick slices scans	k = 0→13
14100 measured reflections	l = −11→11
1587 independent reflections

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) = 0.147	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0818P)2 + 0.0576P] where P = (Fo2 + 2Fc2)/3
1587 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.13 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
O3	0.37522 (15)	−0.24147 (11)	0.61307 (13)	0.0781 (4)
O1	0.05757 (18)	0.21719 (13)	0.30246 (15)	0.0903 (5)
C7	0.16866 (17)	0.02605 (15)	0.40441 (16)	0.0577 (4)
C5	0.32245 (19)	−0.12294 (14)	0.56458 (16)	0.0591 (4)
C3	0.3507 (2)	0.10279 (17)	0.61788 (19)	0.0691 (5)
H3	0.3971	0.17	0.6769	0.083*
C6	0.20840 (18)	−0.10008 (15)	0.43826 (16)	0.0578 (4)
H6	0.1609	−0.1669	0.3791	0.069*
O2	0.1929 (2)	0.35524 (13)	0.46580 (19)	0.1117 (6)
C4	0.39278 (19)	−0.02130 (16)	0.65283 (17)	0.0662 (4)
H4	0.4694	−0.0388	0.7367	0.079*
C2	0.2366 (2)	0.12584 (14)	0.49162 (18)	0.0631 (4)
C8	0.0518 (2)	0.07991 (17)	0.27798 (19)	0.0757 (5)
H8A	0.0874	0.0587	0.1866	0.091*
H8B	−0.0595	0.0471	0.2757	0.091*
C9	0.3066 (3)	−0.34911 (17)	0.5294 (2)	0.0956 (7)
H9A	0.3534	−0.4266	0.5748	0.143*
H9B	0.3318	−0.3432	0.4325	0.143*
H9C	0.1884	−0.3501	0.5244	0.143*
C1	0.1678 (3)	0.24532 (17)	0.4269 (2)	0.0804 (6)

	U11	U22	U33	U12	U13	U23
O3	0.0902 (8)	0.0618 (7)	0.0735 (7)	0.0057 (6)	−0.0102 (6)	0.0080 (5)
O1	0.1053 (10)	0.0749 (9)	0.0911 (9)	0.0277 (7)	0.0182 (8)	0.0207 (7)
C7	0.0555 (8)	0.0608 (9)	0.0574 (8)	0.0033 (6)	0.0117 (6)	0.0053 (6)
C5	0.0602 (8)	0.0573 (10)	0.0576 (8)	0.0000 (6)	0.0046 (7)	0.0042 (6)
C3	0.0743 (10)	0.0658 (10)	0.0678 (10)	−0.0129 (8)	0.0144 (8)	−0.0104 (8)
C6	0.0582 (8)	0.0576 (9)	0.0555 (8)	−0.0025 (6)	0.0038 (6)	−0.0010 (6)
O2	0.1675 (16)	0.0565 (9)	0.1221 (12)	0.0114 (8)	0.0560 (12)	0.0022 (7)
C4	0.0636 (9)	0.0742 (11)	0.0575 (8)	−0.0091 (7)	0.0008 (7)	−0.0032 (7)
C2	0.0676 (9)	0.0564 (10)	0.0687 (10)	−0.0011 (6)	0.0210 (8)	−0.0008 (7)
C8	0.0778 (11)	0.0768 (12)	0.0706 (10)	0.0153 (9)	0.0074 (8)	0.0127 (8)
C9	0.1225 (17)	0.0552 (11)	0.0988 (14)	0.0070 (10)	−0.0099 (12)	−0.0016 (9)
C1	0.1003 (14)	0.0612 (11)	0.0877 (13)	0.0118 (9)	0.0391 (11)	0.0066 (9)

O3—C5	1.3603 (18)	C3—H3	0.93
O3—C9	1.425 (2)	C6—H6	0.93
O1—C1	1.370 (3)	O2—C1	1.209 (2)
O1—C8	1.449 (2)	C4—H4	0.93
C7—C2	1.376 (2)	C2—C1	1.454 (2)
C7—C6	1.378 (2)	C8—H8A	0.97
C7—C8	1.491 (2)	C8—H8B	0.97
C5—C6	1.388 (2)	C9—H9A	0.96
C5—C4	1.402 (2)	C9—H9B	0.96
C3—C4	1.364 (2)	C9—H9C	0.96
C3—C2	1.388 (2)
C5—O3—C9	117.55 (14)	C7—C2—C1	108.43 (16)
C1—O1—C8	110.05 (13)	C3—C2—C1	130.82 (16)
C2—C7—C6	122.13 (14)	O1—C8—C7	104.45 (14)
C2—C7—C8	108.56 (14)	O1—C8—H8A	110.9
C6—C7—C8	129.31 (14)	C7—C8—H8A	110.9
O3—C5—C6	124.38 (14)	O1—C8—H8B	110.9
O3—C5—C4	114.75 (14)	C7—C8—H8B	110.9
C6—C5—C4	120.87 (15)	H8A—C8—H8B	108.9
C4—C3—C2	118.08 (15)	O3—C9—H9A	109.5
C4—C3—H3	121	O3—C9—H9B	109.5
C2—C3—H3	121	H9A—C9—H9B	109.5
C7—C6—C5	117.03 (14)	O3—C9—H9C	109.5
C7—C6—H6	121.5	H9A—C9—H9C	109.5
C5—C6—H6	121.5	H9B—C9—H9C	109.5
C3—C4—C5	121.14 (15)	O2—C1—O1	120.56 (18)
C3—C4—H4	119.4	O2—C1—C2	131.0 (2)
C5—C4—H4	119.4	O1—C1—C2	108.49 (15)
C7—C2—C3	120.75 (15)
C9—O3—C5—C6	−1.0 (2)	C8—C7—C2—C1	0.17 (17)
C9—O3—C5—C4	179.11 (15)	C4—C3—C2—C7	−0.2 (2)
C2—C7—C6—C5	−0.6 (2)	C4—C3—C2—C1	179.72 (15)
C8—C7—C6—C5	−179.90 (15)	C1—O1—C8—C7	1.42 (18)
O3—C5—C6—C7	−179.79 (13)	C2—C7—C8—O1	−0.95 (16)
C4—C5—C6—C7	0.1 (2)	C6—C7—C8—O1	178.38 (14)
C2—C3—C4—C5	−0.3 (2)	C8—O1—C1—O2	178.93 (16)
O3—C5—C4—C3	−179.70 (13)	C8—O1—C1—C2	−1.36 (19)
C6—C5—C4—C3	0.4 (2)	C7—C2—C1—O2	−179.60 (18)
C6—C7—C2—C3	0.7 (2)	C3—C2—C1—O2	0.5 (3)
C8—C7—C2—C3	−179.91 (15)	C7—C2—C1—O1	0.73 (19)
C6—C7—C2—C1	−179.22 (13)	C3—C2—C1—O1	−179.17 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.54	3.419 (2)	157
C8—H8A···O2ii	0.97	2.52	3.372 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.54	3.419 (2)	157
C8—H8A⋯O2ii	0.97	2.52	3.372 (2)	146

Symmetry codes: (i) ; (ii) .