1-(1,3-Benzodioxol-5-yl)ethanone.

In the title compound, C(9)H(8)O(3), the dihedral angle between the mean planes of the benzene and dioxole rings is 1.4 (8)°, with the dioxole group in a slightly distorted envelope configuration with the flap C atom displaced by 0.0645 Å from the plane through the other four atoms. In the crystal, weak inter-molecular C-H⋯O hydrogen-bond inter-actions link the mol-ecules into chains propagating in [011]. The crystal packing exhibits weak π-π inter-actions as evidenced by the relatively short distances [3.801 (9) Å] between the centroids of adjacent benzene rings.

Related literature

For the pharmaceutical properties of compounds containing the 1,3-dioxolyl group, see: Gabrielsen et al. (1992 ▶); Krause & Goeber (1972 ▶); Ma et al. (1987a ▶,b ▶); Ohta & Kimoto (1976 ▶); For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Jasinski et al. (2008 ▶); Yathirajan et al. (2007 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For MOPAC AM1 calculations, see: Schmidt & Polik (2007 ▶).

Experimental

Crystal data

C9H8O3

M = 164.15

Monoclinic,

a = 9.4697 (3) Å

b = 10.8445 (3) Å

c = 7.5148 (3) Å

β = 105.973 (3)°

V = 741.93 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 200 K

0.58 × 0.45 × 0.26 mm

Data collection

Oxford Diffraction R Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.909, T max = 0.972

12470 measured reflections

3061 independent reflections

2215 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.133

S = 1.03

3061 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001352/im2174sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001352/im2174Isup2.hkl

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

C9H8O3	F(000) = 344
Mr = 164.15	Dx = 1.470 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5168 reflections
a = 9.4697 (3) Å	θ = 4.8–34.7°
b = 10.8445 (3) Å	µ = 0.11 mm−1
c = 7.5148 (3) Å	T = 200 K
β = 105.973 (3)°	Irregular plate, colorless
V = 741.93 (4) Å3	0.58 × 0.45 × 0.26 mm
Z = 4

Oxford Diffraction R Gemini diffractometer	3061 independent reflections
Radiation source: fine-focus sealed tube	2215 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 10.5081 pixels mm-1	θmax = 34.8°, θmin = 4.9°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −17→15
Tmin = 0.909, Tmax = 0.972	l = −11→11
12470 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0852P)2] where P = (Fo2 + 2Fc2)/3
3061 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.28 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	0.19844 (7)	0.26081 (7)	0.45409 (11)	0.03260 (19)
O2	0.12787 (7)	0.42705 (7)	0.60401 (10)	0.02944 (17)
O3	0.76739 (8)	0.26971 (7)	0.62415 (11)	0.03273 (18)
C1	0.07627 (10)	0.31692 (10)	0.50175 (15)	0.0315 (2)
H1A	−0.0023	0.3370	0.3882	0.038*
H1B	0.0357	0.2596	0.5777	0.038*
C2	0.27739 (9)	0.42276 (8)	0.64441 (11)	0.02067 (17)
C3	0.37564 (9)	0.50450 (8)	0.74958 (12)	0.02310 (18)
H3A	0.3448	0.5732	0.8079	0.028*
C4	0.52406 (9)	0.48140 (8)	0.76650 (12)	0.02156 (17)
H4A	0.5960	0.5353	0.8397	0.026*
C5	0.56965 (8)	0.38161 (8)	0.67914 (11)	0.01868 (16)
C6	0.46499 (9)	0.30025 (8)	0.56785 (12)	0.02042 (17)
H6A	0.4936	0.2329	0.5048	0.024*
C7	0.32064 (9)	0.32334 (8)	0.55556 (11)	0.02051 (17)
C8	0.72805 (9)	0.35800 (8)	0.70045 (12)	0.02201 (18)
C9	0.84055 (10)	0.44275 (10)	0.82066 (14)	0.0293 (2)
H9A	0.9373	0.4250	0.8032	0.044*
H9B	0.8436	0.4298	0.9507	0.044*
H9C	0.8139	0.5286	0.7863	0.044*

	U11	U22	U33	U12	U13	U23
O1	0.0185 (3)	0.0348 (4)	0.0419 (4)	−0.0031 (3)	0.0041 (3)	−0.0136 (3)
O2	0.0162 (3)	0.0337 (4)	0.0373 (4)	0.0036 (2)	0.0055 (3)	−0.0046 (3)
O3	0.0236 (3)	0.0311 (4)	0.0461 (4)	0.0029 (3)	0.0140 (3)	−0.0052 (3)
C1	0.0180 (4)	0.0394 (5)	0.0362 (5)	−0.0029 (4)	0.0061 (4)	−0.0063 (4)
C2	0.0166 (3)	0.0237 (4)	0.0217 (4)	0.0032 (3)	0.0054 (3)	0.0019 (3)
C3	0.0227 (4)	0.0221 (4)	0.0248 (4)	0.0030 (3)	0.0071 (3)	−0.0028 (3)
C4	0.0204 (4)	0.0209 (4)	0.0227 (4)	−0.0010 (3)	0.0048 (3)	−0.0013 (3)
C5	0.0172 (3)	0.0191 (4)	0.0201 (4)	0.0006 (3)	0.0056 (3)	0.0024 (3)
C6	0.0203 (4)	0.0188 (4)	0.0230 (4)	0.0013 (3)	0.0075 (3)	−0.0009 (3)
C7	0.0178 (3)	0.0210 (4)	0.0217 (4)	−0.0014 (3)	0.0036 (3)	−0.0005 (3)
C8	0.0186 (3)	0.0227 (4)	0.0261 (4)	0.0004 (3)	0.0084 (3)	0.0039 (3)
C9	0.0186 (4)	0.0328 (5)	0.0353 (5)	−0.0031 (3)	0.0056 (3)	−0.0003 (4)

O1—C7	1.3765 (10)	C4—C5	1.3945 (12)
O1—C1	1.4370 (12)	C4—H4A	0.9500
O2—C2	1.3648 (10)	C5—C6	1.4157 (11)
O2—C1	1.4314 (12)	C5—C8	1.4862 (11)
O3—C8	1.2256 (11)	C6—C7	1.3676 (11)
C1—H1A	0.9900	C6—H6A	0.9500
C1—H1B	0.9900	C8—C9	1.5053 (12)
C2—C3	1.3679 (12)	C9—H9A	0.9800
C2—C7	1.3879 (12)	C9—H9B	0.9800
C3—C4	1.3985 (11)	C9—H9C	0.9800
C3—H3A	0.9500
C7—O1—C1	105.37 (7)	C4—C5—C8	121.13 (7)
C2—O2—C1	105.72 (7)	C6—C5—C8	118.56 (7)
O2—C1—O1	107.93 (7)	C7—C6—C5	116.75 (8)
O2—C1—H1A	110.1	C7—C6—H6A	121.6
O1—C1—H1A	110.1	C5—C6—H6A	121.6
O2—C1—H1B	110.1	C6—C7—O1	128.28 (8)
O1—C1—H1B	110.1	C6—C7—C2	122.11 (8)
H1A—C1—H1B	108.4	O1—C7—C2	109.56 (7)
O2—C2—C3	127.26 (8)	O3—C8—C5	120.79 (8)
O2—C2—C7	110.18 (7)	O3—C8—C9	120.11 (8)
C3—C2—C7	122.51 (8)	C5—C8—C9	119.09 (8)
C2—C3—C4	116.31 (8)	C8—C9—H9A	109.5
C2—C3—H3A	121.8	C8—C9—H9B	109.5
C4—C3—H3A	121.8	H9A—C9—H9B	109.5
C5—C4—C3	121.99 (8)	C8—C9—H9C	109.5
C5—C4—H4A	119.0	H9A—C9—H9C	109.5
C3—C4—H4A	119.0	H9B—C9—H9C	109.5
C4—C5—C6	120.31 (7)
C2—O2—C1—O1	−10.84 (10)	C5—C6—C7—C2	1.19 (13)
C7—O1—C1—O2	10.94 (10)	C1—O1—C7—C6	175.70 (9)
C1—O2—C2—C3	−175.94 (9)	C1—O1—C7—C2	−6.94 (10)
C1—O2—C2—C7	6.63 (10)	O2—C2—C7—C6	177.78 (8)
O2—C2—C3—C4	−178.36 (8)	C3—C2—C7—C6	0.21 (14)
C7—C2—C3—C4	−1.22 (13)	O2—C2—C7—O1	0.22 (10)
C2—C3—C4—C5	0.83 (13)	C3—C2—C7—O1	−177.35 (8)
C3—C4—C5—C6	0.55 (13)	C4—C5—C8—O3	179.58 (8)
C3—C4—C5—C8	−179.39 (8)	C6—C5—C8—O3	−0.36 (12)
C4—C5—C6—C7	−1.54 (12)	C4—C5—C8—C9	0.81 (12)
C8—C5—C6—C7	178.40 (7)	C6—C5—C8—C9	−179.12 (8)
C5—C6—C7—O1	178.26 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O3i	0.95	2.50	3.423 (1)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O3i	0.95	2.50	3.423 (1)	165

Symmetry code: (i) .