6-Meth-oxyisobenzofuran-1(3H)-one.

In the title compound, C(9)H(8)O(3), the mol-ecular skeleton is almost planar [r.m.s. deviation = 0.016 (2) Å]. Weak inter-molecular C-H⋯O and C-H⋯π inter-actions consolidate the crystal packing, with the mol-ecules stacking in the [101] direction.

Related literature

For the biological activity of isobenzofuran-1(3H)-one, see: Brady et al. (2000 ▶); Huang et al. (2012) ▶; Cardozo et al. (2005 ▶); Yoganathan et al. (2003 ▶); Demuner et al. (2006 ▶). For related structures, see: Sun et al. (2009 ▶); Mendenhall et al. (2003 ▶).

Experimental

Crystal data

C9H8O3

M = 164.15

Monoclinic,

a = 9.2922 (19) Å

b = 8.4982 (12) Å

c = 9.786 (2) Å

β = 90.471 (15)°

V = 772.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.28 × 0.17 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

3304 measured reflections

1741 independent reflections

1285 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.166

S = 1.12

1741 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039074/cv5338sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039074/cv5338Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039074/cv5338Isup3.cml

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

C9H8O3	F(000) = 344
Mr = 164.15	Dx = 1.411 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.2922 (19) Å	Cell parameters from 3082 reflections
b = 8.4982 (12) Å	θ = 2.1–27.5°
c = 9.786 (2) Å	µ = 0.11 mm−1
β = 90.471 (15)°	T = 293 K
V = 772.8 (2) Å3	Prism, colourless
Z = 4	0.28 × 0.17 × 0.12 mm

Nonius KappaCCD diffractometer	1285 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.036
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
Detector resolution: 9 pixels mm-1	h = −12→12
CCD rotation images, thick slices scans	k = −10→11
3304 measured reflections	l = −12→12
1741 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0943P)2 + 0.032P] where P = (Fo2 + 2Fc2)/3
1741 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.18 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	0.93834 (12)	0.04009 (14)	0.16871 (11)	0.0695 (4)
O2	0.79489 (14)	−0.11746 (14)	0.04458 (12)	0.0752 (4)
O3	0.54600 (12)	0.40633 (13)	−0.19372 (11)	0.0699 (4)
C1	0.83141 (17)	0.0134 (2)	0.07489 (15)	0.0612 (4)
C2	0.77893 (16)	0.16711 (17)	0.02593 (13)	0.0552 (4)
C3	0.67205 (15)	0.19885 (18)	−0.07089 (14)	0.0569 (4)
H3	0.6212	0.1185	−0.114	0.068*
C4	0.64497 (16)	0.35569 (18)	−0.09995 (14)	0.0568 (4)
C5	0.72174 (17)	0.47477 (18)	−0.03217 (16)	0.0632 (4)
H5	0.7013	0.5794	−0.0524	0.076*
C6	0.82660 (17)	0.44069 (19)	0.06357 (16)	0.0639 (4)
H6	0.8766	0.5208	0.108	0.077*
C7	0.85594 (16)	0.28364 (18)	0.09213 (14)	0.0572 (4)
C8	0.96195 (18)	0.2080 (2)	0.18656 (16)	0.0663 (5)
H8A	1.0596	0.2365	0.1624	0.08*
H8B	0.9448	0.2392	0.2804	0.08*
C9	0.45913 (19)	0.2893 (2)	−0.25875 (18)	0.0730 (5)
H9A	0.3942	0.3389	−0.3222	0.11*
H9B	0.4051	0.2336	−0.191	0.11*
H9C	0.5197	0.2169	−0.3067	0.11*

	U11	U22	U33	U12	U13	U23
O1	0.0805 (7)	0.0576 (7)	0.0702 (7)	0.0088 (5)	−0.0046 (5)	0.0056 (5)
O2	0.0934 (9)	0.0475 (7)	0.0847 (8)	0.0000 (5)	0.0030 (6)	0.0033 (5)
O3	0.0797 (7)	0.0492 (7)	0.0804 (7)	−0.0024 (5)	−0.0172 (6)	0.0022 (5)
C1	0.0700 (9)	0.0536 (9)	0.0602 (8)	0.0018 (7)	0.0085 (7)	0.0018 (6)
C2	0.0635 (8)	0.0479 (8)	0.0541 (7)	0.0004 (6)	0.0070 (6)	0.0000 (6)
C3	0.0651 (8)	0.0457 (8)	0.0599 (8)	−0.0047 (6)	0.0027 (6)	−0.0034 (6)
C4	0.0635 (8)	0.0480 (8)	0.0588 (8)	−0.0014 (6)	−0.0003 (6)	−0.0001 (6)
C5	0.0757 (9)	0.0428 (8)	0.0708 (9)	0.0005 (6)	−0.0035 (7)	−0.0013 (6)
C6	0.0734 (9)	0.0496 (8)	0.0686 (9)	−0.0049 (7)	−0.0032 (7)	−0.0081 (7)
C7	0.0633 (8)	0.0524 (9)	0.0561 (7)	−0.0001 (6)	0.0046 (6)	−0.0021 (6)
C8	0.0728 (9)	0.0610 (10)	0.0649 (9)	0.0037 (7)	−0.0022 (7)	−0.0042 (7)
C9	0.0790 (10)	0.0593 (10)	0.0805 (10)	−0.0097 (8)	−0.0147 (8)	0.0019 (8)

O1—C1	1.366 (2)	C5—C6	1.377 (2)
O1—C8	1.454 (2)	C5—H5	0.93
O2—C1	1.199 (2)	C6—C7	1.390 (2)
O3—C4	1.3635 (19)	C6—H6	0.93
O3—C9	1.427 (2)	C7—C8	1.491 (2)
C1—C2	1.473 (2)	C8—H8A	0.97
C2—C7	1.380 (2)	C8—H8B	0.97
C2—C3	1.393 (2)	C9—H9A	0.96
C3—C4	1.385 (2)	C9—H9B	0.96
C3—H3	0.93	C9—H9C	0.96
C4—C5	1.402 (2)
C1—O1—C8	110.59 (12)	C5—C6—H6	120.8
C4—O3—C9	117.14 (13)	C7—C6—H6	120.8
O2—C1—O1	121.50 (16)	C2—C7—C6	119.63 (15)
O2—C1—C2	130.52 (17)	C2—C7—C8	108.60 (14)
O1—C1—C2	107.98 (14)	C6—C7—C8	131.77 (14)
C7—C2—C3	122.97 (15)	O1—C8—C7	104.50 (12)
C7—C2—C1	108.34 (15)	O1—C8—H8A	110.9
C3—C2—C1	128.69 (14)	C7—C8—H8A	110.9
C4—C3—C2	116.94 (14)	O1—C8—H8B	110.9
C4—C3—H3	121.5	C7—C8—H8B	110.9
C2—C3—H3	121.5	H8A—C8—H8B	108.9
O3—C4—C3	124.20 (14)	O3—C9—H9A	109.5
O3—C4—C5	115.37 (14)	O3—C9—H9B	109.5
C3—C4—C5	120.43 (15)	H9A—C9—H9B	109.5
C6—C5—C4	121.64 (15)	O3—C9—H9C	109.5
C6—C5—H5	119.2	H9A—C9—H9C	109.5
C4—C5—H5	119.2	H9B—C9—H9C	109.5
C5—C6—C7	118.38 (15)
C8—O1—C1—O2	179.83 (13)	O3—C4—C5—C6	−178.97 (12)
C8—O1—C1—C2	−0.01 (16)	C3—C4—C5—C6	0.7 (2)
O2—C1—C2—C7	−179.93 (15)	C4—C5—C6—C7	0.2 (2)
O1—C1—C2—C7	−0.11 (16)	C3—C2—C7—C6	0.6 (2)
O2—C1—C2—C3	−0.6 (3)	C1—C2—C7—C6	179.99 (12)
O1—C1—C2—C3	179.23 (12)	C3—C2—C7—C8	−179.21 (12)
C7—C2—C3—C4	0.2 (2)	C1—C2—C7—C8	0.18 (16)
C1—C2—C3—C4	−179.01 (12)	C5—C6—C7—C2	−0.8 (2)
C9—O3—C4—C3	4.2 (2)	C5—C6—C7—C8	178.95 (14)
C9—O3—C4—C5	−176.13 (13)	C1—O1—C8—C7	0.11 (15)
C2—C3—C4—O3	178.74 (12)	C2—C7—C8—O1	−0.18 (15)
C2—C3—C4—C5	−0.9 (2)	C6—C7—C8—O1	−179.96 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O2i	0.96	2.55	3.490 (2)	165
C8—H8B···Cg1ii	0.97	2.84	3.637 (2)	140
C9—H9C···Cg1iii	0.96	2.91	3.744 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O2i	0.96	2.55	3.490 (2)	165
C8—H8B⋯Cg1ii	0.97	2.84	3.637 (2)	140
C9—H9C⋯Cg1iii	0.96	2.91	3.744 (2)	146

Symmetry codes: (i) ; (ii) ; (iii) .