3,3-Dimethyl-2-benzofuran-1(3H)-one.

In the title compound, C(10)H(10)O(2), all the non-H atoms except the methyl C atoms lie on a crystallographic mirror plane. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into zigzag chains running parallel to [100]. Weak π-π stacking inter-actions between the benzene rings [centroid-centroid distance = 3.9817 (5) Å] link the chains in the [010] direction.

Related literature

For related structures, see: Fun et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C10H10O2

M = 162.18

Orthorhombic,

a = 14.3537 (9) Å

b = 7.0069 (5) Å

c = 8.2605 (5) Å

V = 830.80 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 123 K

0.55 × 0.44 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: refined from ΔF (XABS2; Parkin et al., 1995 ▶) T min = 0.952, T max = 0.974

1840 measured reflections

1840 independent reflections

1454 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.133

S = 1.09

1840 reflections

71 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052913/hb6560sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052913/hb6560Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052913/hb6560Isup3.cml

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

C10H10O2	F(000) = 344
Mr = 162.18	Dx = 1.297 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1444 reflections
a = 14.3537 (9) Å	θ = 2.8–35.2°
b = 7.0069 (5) Å	µ = 0.09 mm−1
c = 8.2605 (5) Å	T = 123 K
V = 830.80 (9) Å3	Prism, colourless
Z = 4	0.55 × 0.44 × 0.30 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	1840 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1454 reflections with I > 2σ(I)
graphite	Rint = 0.000
Detector resolution: 10.5081 pixels mm-1	θmax = 35.2°, θmin = 2.8°
ω scans	h = 0→22
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	k = 0→11
Tmin = 0.952, Tmax = 0.974	l = 0→13
1840 measured 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.0987P] where P = (Fo2 + 2Fc2)/3
1840 reflections	(Δ/σ)max < 0.001
71 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. Absorption correction: XABS2 (Parkin et al., 1995); cubic fit to sinθ/λ - 24 parameters

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.99217 (7)	0.25000	0.38584 (11)	0.0216 (3)
O2	1.13652 (7)	0.25000	0.28045 (13)	0.0260 (3)
C1	0.90567 (9)	0.25000	0.14603 (15)	0.0159 (3)
C2	0.83829 (9)	0.25000	0.02623 (16)	0.0193 (3)
C3	0.86910 (10)	0.25000	−0.13404 (16)	0.0211 (3)
C4	0.96384 (10)	0.25000	−0.17273 (16)	0.0208 (3)
C5	1.03071 (9)	0.25000	−0.05143 (16)	0.0192 (3)
C6	0.99948 (9)	0.25000	0.10807 (15)	0.0165 (3)
C7	1.05334 (9)	0.25000	0.25962 (15)	0.0189 (3)
C8	0.89464 (9)	0.25000	0.32851 (15)	0.0175 (3)
C9	0.84773 (7)	0.07067 (15)	0.39183 (12)	0.0229 (3)
H2	0.77510	0.25000	0.05140	0.0230*
H3	0.82540	0.25000	−0.21720	0.0250*
H4	0.98220	0.25000	−0.28070	0.0250*
H5	1.09400	0.25000	−0.07580	0.0230*
H9A	0.88010	−0.03960	0.35190	0.0340*
H9B	0.78420	0.06740	0.35560	0.0340*
H9C	0.84920	0.07080	0.50800	0.0340*

	U11	U22	U33	U12	U13	U23
O1	0.0185 (4)	0.0326 (5)	0.0136 (4)	0.0000	−0.0019 (4)	0.0000
O2	0.0169 (4)	0.0368 (6)	0.0242 (5)	0.0000	−0.0042 (4)	0.0000
C1	0.0169 (5)	0.0170 (5)	0.0137 (5)	0.0000	0.0004 (4)	0.0000
C2	0.0176 (5)	0.0251 (6)	0.0153 (5)	0.0000	−0.0002 (5)	0.0000
C3	0.0220 (6)	0.0270 (6)	0.0143 (5)	0.0000	−0.0021 (5)	0.0000
C4	0.0246 (6)	0.0248 (6)	0.0131 (5)	0.0000	0.0025 (5)	0.0000
C5	0.0185 (5)	0.0213 (5)	0.0177 (5)	0.0000	0.0031 (5)	0.0000
C6	0.0176 (5)	0.0173 (5)	0.0147 (5)	0.0000	0.0003 (4)	0.0000
C7	0.0182 (6)	0.0214 (5)	0.0172 (5)	0.0000	−0.0011 (5)	0.0000
C8	0.0164 (5)	0.0232 (6)	0.0130 (5)	0.0000	−0.0007 (4)	0.0000
C9	0.0259 (5)	0.0244 (4)	0.0185 (4)	−0.0011 (4)	0.0028 (3)	0.0028 (3)

O1—C7	1.3631 (16)	C6—C7	1.4714 (18)
O1—C8	1.4779 (16)	C8—C9	1.5185 (13)
O2—C7	1.2063 (16)	C8—C9i	1.5185 (13)
C1—C2	1.3837 (18)	C2—H2	0.9300
C1—C6	1.3826 (18)	C3—H3	0.9300
C1—C8	1.5157 (18)	C4—H4	0.9300
C2—C3	1.3958 (19)	C5—H5	0.9300
C3—C4	1.397 (2)	C9—H9A	0.9600
C4—C5	1.3875 (19)	C9—H9B	0.9600
C5—C6	1.3917 (18)	C9—H9C	0.9600
C7—O1—C8	111.41 (9)	C1—C8—C9	112.89 (7)
C2—C1—C6	121.23 (12)	C1—C8—C9i	112.89 (7)
C2—C1—C8	129.66 (12)	C9—C8—C9i	111.68 (10)
C6—C1—C8	109.11 (11)	C1—C2—H2	121.00
C1—C2—C3	117.19 (12)	C3—C2—H2	121.00
C2—C3—C4	121.70 (12)	C2—C3—H3	119.00
C3—C4—C5	120.54 (12)	C4—C3—H3	119.00
C4—C5—C6	117.44 (12)	C3—C4—H4	120.00
C1—C6—C5	121.90 (12)	C5—C4—H4	120.00
C1—C6—C7	108.59 (11)	C4—C5—H5	121.00
C5—C6—C7	129.51 (12)	C6—C5—H5	121.00
O1—C7—O2	121.90 (12)	C8—C9—H9A	109.00
O1—C7—C6	108.20 (11)	C8—C9—H9B	109.00
O2—C7—C6	129.90 (12)	C8—C9—H9C	110.00
O1—C8—C1	102.69 (10)	H9A—C9—H9B	109.00
O1—C8—C9	108.04 (7)	H9A—C9—H9C	109.00
O1—C8—C9i	108.04 (7)	H9B—C9—H9C	109.00
C7—O1—C8—C9	119.51 (7)	C8—C1—C6—C5	180.00
C8—O1—C7—O2	180.00	C2—C1—C8—C9	63.92 (8)
C8—O1—C7—C6	0.00	C1—C2—C3—C4	0.00
C7—O1—C8—C1	0.00	C2—C3—C4—C5	0.00
C8—C1—C2—C3	180.00	C3—C4—C5—C6	0.00
C2—C1—C6—C5	0.00	C4—C5—C6—C1	0.00
C2—C1—C6—C7	180.00	C4—C5—C6—C7	180.00
C6—C1—C2—C3	0.00	C1—C6—C7—O2	180.00
C6—C1—C8—O1	0.00	C5—C6—C7—O1	180.00
C6—C1—C8—C9	−116.08 (8)	C5—C6—C7—O2	0.00
C8—C1—C6—C7	0.00	C1—C6—C7—O1	0.00
C2—C1—C8—O1	180.00

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ii	0.93	2.43	3.3072 (17)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.93	2.43	3.3072 (17)	158

Symmetry code: (i) .