1-(1,3-Benzodioxol-5-yl)butan-1-one.

In the mol-ecule of the title compound, C(11)H(12)O(3), the dioxole ring adopts an envelope conformation. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains.

Related literature

For general background, see: Nichols (1986 ▶). For a related structure, see: Zhu (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H12O3

M = 192.21

Monoclinic,

a = 11.944 (2) Å

b = 11.143 (2) Å

c = 7.4600 (15) Å

β = 100.69 (3)°

V = 975.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.972, T max = 0.991

1869 measured reflections

1775 independent reflections

1166 reflections with I > 2σ(I)

R int = 0.045

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.174

S = 1.01

1775 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040300/hk2590sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040300/hk2590Isup2.hkl

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

C11H12O3	F(000) = 408
Mr = 192.21	Dx = 1.309 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.944 (2) Å	θ = 9–12°
b = 11.143 (2) Å	µ = 0.10 mm−1
c = 7.4600 (15) Å	T = 298 K
β = 100.69 (3)°	Block, colourless
V = 975.6 (3) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1166 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
graphite	θmax = 25.3°, θmin = 1.7°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = 0→13
Tmin = 0.972, Tmax = 0.991	l = −8→8
1869 measured reflections	3 standard reflections every 120 min
1775 independent reflections	intensity decay: 1%

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.05P)2 + 2.1P] where P = (Fo2 + 2Fc2)/3
1775 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.30 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	0.4098 (2)	0.2566 (2)	0.9257 (3)	0.0479 (7)
O2	0.8478 (2)	0.2368 (2)	1.0244 (4)	0.0521 (7)
O3	0.8912 (2)	0.0624 (2)	0.8880 (3)	0.0475 (7)
C1	0.1275 (3)	0.0544 (4)	0.6397 (6)	0.0625 (12)
H1A	0.0552	0.0930	0.6344	0.094*
H1B	0.1286	−0.0198	0.7055	0.094*
H1C	0.1394	0.0384	0.5181	0.094*
C2	0.2211 (3)	0.1353 (3)	0.7358 (6)	0.0486 (10)
H2A	0.2172	0.2110	0.6708	0.058*
H2B	0.2075	0.1518	0.8576	0.058*
C3	0.3397 (3)	0.0849 (3)	0.7510 (4)	0.0347 (8)
H3A	0.3543	0.0698	0.6293	0.042*
H3B	0.3437	0.0086	0.8145	0.042*
C4	0.4319 (3)	0.1669 (3)	0.8506 (4)	0.0284 (7)
C5	0.5527 (2)	0.1323 (3)	0.8527 (4)	0.0268 (7)
C6	0.6389 (3)	0.2119 (3)	0.9436 (4)	0.0303 (7)
H6A	0.6211	0.2819	1.0002	0.036*
C7	0.7489 (3)	0.1792 (3)	0.9424 (4)	0.0362 (8)
C8	0.7769 (3)	0.0757 (3)	0.8658 (4)	0.0342 (8)
C9	0.6943 (3)	−0.0028 (3)	0.7756 (4)	0.0332 (8)
H9A	0.7136	−0.0722	0.7190	0.040*
C10	0.5818 (3)	0.0280 (3)	0.7748 (4)	0.0301 (7)
H10A	0.5243	−0.0235	0.7199	0.036*
C11	0.9378 (3)	0.1710 (3)	0.9731 (6)	0.0503 (10)
H11A	0.9952	0.1528	1.0796	0.060*
H11B	0.9731	0.2175	0.8887	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0483 (15)	0.0414 (15)	0.0506 (16)	0.0091 (11)	0.0003 (12)	−0.0123 (13)
O2	0.0351 (13)	0.0524 (16)	0.0651 (18)	−0.0039 (12)	−0.0004 (12)	−0.0165 (14)
O3	0.0378 (14)	0.0530 (16)	0.0520 (16)	0.0046 (11)	0.0089 (11)	−0.0057 (13)
C1	0.039 (2)	0.078 (3)	0.066 (3)	−0.006 (2)	−0.0016 (19)	−0.017 (2)
C2	0.048 (2)	0.041 (2)	0.053 (2)	−0.0024 (17)	−0.0016 (17)	−0.0038 (18)
C3	0.0429 (19)	0.0340 (18)	0.0241 (17)	−0.0047 (14)	−0.0021 (14)	−0.0017 (14)
C4	0.0428 (18)	0.0209 (15)	0.0211 (15)	0.0085 (13)	0.0051 (13)	−0.0006 (13)
C5	0.0310 (16)	0.0301 (17)	0.0180 (15)	−0.0011 (13)	0.0015 (12)	0.0033 (13)
C6	0.0362 (17)	0.0267 (16)	0.0292 (17)	0.0033 (13)	0.0095 (13)	−0.0073 (13)
C7	0.0361 (18)	0.0399 (19)	0.0306 (18)	−0.0056 (15)	0.0016 (14)	−0.0005 (15)
C8	0.0432 (19)	0.0326 (18)	0.0262 (17)	0.0066 (14)	0.0043 (14)	−0.0014 (14)
C9	0.0402 (19)	0.0294 (17)	0.0309 (17)	0.0037 (14)	0.0093 (14)	−0.0076 (14)
C10	0.0425 (19)	0.0259 (16)	0.0207 (15)	−0.0017 (13)	0.0030 (13)	−0.0028 (13)
C11	0.041 (2)	0.053 (2)	0.057 (2)	−0.0099 (18)	0.0085 (17)	−0.004 (2)

O1—C4	1.200 (4)	C3—H3B	0.9700
O2—C7	1.384 (4)	C4—C5	1.491 (4)
O2—C11	1.410 (4)	C5—C10	1.372 (4)
O3—C8	1.353 (4)	C5—C6	1.432 (4)
O3—C11	1.431 (4)	C6—C7	1.364 (4)
C1—C2	1.510 (5)	C6—H6A	0.9300
C1—H1A	0.9600	C7—C8	1.356 (5)
C1—H1B	0.9600	C8—C9	1.395 (4)
C1—H1C	0.9600	C9—C10	1.385 (4)
C2—C3	1.508 (5)	C9—H9A	0.9300
C2—H2A	0.9700	C10—H10A	0.9300
C2—H2B	0.9700	C11—H11A	0.9700
C3—C4	1.515 (4)	C11—H11B	0.9700
C3—H3A	0.9700
C7—O2—C11	105.7 (3)	C10—C5—C4	122.4 (3)
C8—O3—C11	105.2 (3)	C6—C5—C4	117.0 (3)
C2—C1—H1A	109.5	C7—C6—C5	116.1 (3)
C2—C1—H1B	109.5	C7—C6—H6A	122.0
H1A—C1—H1B	109.5	C5—C6—H6A	122.0
C2—C1—H1C	109.5	C8—C7—C6	122.9 (3)
H1A—C1—H1C	109.5	C8—C7—O2	108.9 (3)
H1B—C1—H1C	109.5	C6—C7—O2	128.1 (3)
C3—C2—C1	114.6 (3)	O3—C8—C7	111.3 (3)
C3—C2—H2A	108.6	O3—C8—C9	126.7 (3)
C1—C2—H2A	108.6	C7—C8—C9	121.9 (3)
C3—C2—H2B	108.6	C10—C9—C8	116.4 (3)
C1—C2—H2B	108.6	C10—C9—H9A	121.8
H2A—C2—H2B	107.6	C8—C9—H9A	121.8
C2—C3—C4	113.5 (3)	C5—C10—C9	122.0 (3)
C2—C3—H3A	108.9	C5—C10—H10A	119.0
C4—C3—H3A	108.9	C9—C10—H10A	119.0
C2—C3—H3B	108.9	O2—C11—O3	107.9 (3)
C4—C3—H3B	108.9	O2—C11—H11A	110.1
H3A—C3—H3B	107.7	O3—C11—H11A	110.1
O1—C4—C5	120.5 (3)	O2—C11—H11B	110.1
O1—C4—C3	121.9 (3)	O3—C11—H11B	110.1
C5—C4—C3	117.6 (3)	H11A—C11—H11B	108.4
C10—C5—C6	120.6 (3)
C1—C2—C3—C4	−179.1 (3)	C11—O3—C8—C7	−4.7 (4)
C2—C3—C4—O1	7.5 (5)	C11—O3—C8—C9	174.6 (3)
C2—C3—C4—C5	−172.6 (3)	C6—C7—C8—O3	−178.0 (3)
O1—C4—C5—C10	177.3 (3)	O2—C7—C8—O3	−1.8 (4)
C3—C4—C5—C10	−2.6 (4)	C6—C7—C8—C9	2.7 (5)
O1—C4—C5—C6	−1.5 (4)	O2—C7—C8—C9	178.9 (3)
C3—C4—C5—C6	178.6 (3)	O3—C8—C9—C10	178.2 (3)
C10—C5—C6—C7	1.8 (4)	C7—C8—C9—C10	−2.6 (5)
C4—C5—C6—C7	−179.4 (3)	C6—C5—C10—C9	−2.0 (5)
C5—C6—C7—C8	−2.2 (5)	C4—C5—C10—C9	179.3 (3)
C5—C6—C7—O2	−177.6 (3)	C8—C9—C10—C5	2.3 (5)
C11—O2—C7—C8	7.6 (4)	C7—O2—C11—O3	−10.4 (4)
C11—O2—C7—C6	−176.5 (4)	C8—O3—C11—O2	9.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1i	0.93	2.53	3.209 (4)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.93	2.53	3.209 (4)	130

Symmetry code: (i) .