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

Cheng, W.; Lv, R.; Zhu, H.-J.

doi:10.1107/S1600536808040300

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o179

doi:10.1107/S1600536808040300

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

Wei Cheng,^a Ran Lv ^a and Hong-Jun Zhu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 29 November 2008; accepted 30 November 2008; online 20 December 2008)

In the molecule of the title compound, C₁₁H₁₂O₃, the dioxole ring adopts an envelope conformation. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules 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_r = 192.21
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.070
wR(F²) = 0.174
S = 1.01
1775 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

The title compound is an important medicine intermediate used to synthesize 3,4-methylenedioxy-alpha-ethyl-N-methylphenethylamine, which is a lesser-known hallucinogenic phenethylamine (Nichols, 1986). We report herein its crystal structure, which is of interest to us in the field.

In the molecule of title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring B (C5–C10) is, of course, planar, while ring A (O2/O3/C7/C8/C11) adopts envelope conformation with C11 atom displaced by 0.147 (3) Å from the plane of the other ring atoms. Atoms O1, C3 and C4 are -0.032 (3), 0.050 (3) and 0.044 (3) Å away from the plane of the benzene ring.

In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

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

Experimental top

The title compound was synthesized according to a literature method (Zhu, 2003). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (0.3 g) in ethanol (25 ml), and evaporating the solvent slowly at room temperature for about 4 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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 (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₁H₁₂O₃	F(000) = 408
M_r = 192.21	D_x = 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

Data collection top

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

Refinement top

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 = 1.01	w = 1/[σ²(F_o²) + (0.05P)² + 2.1P] where P = (F_o² + 2F_c²)/3
1775 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₁H₁₂O₃	V = 975.6 (3) Å³
M_r = 192.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.944 (2) Å	µ = 0.10 mm⁻¹
b = 11.143 (2) Å	T = 298 K
c = 7.4600 (15) Å	0.30 × 0.20 × 0.10 mm
β = 100.69 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1166 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.045
T_min = 0.972, T_max = 0.991	3 standard reflections every 120 min
1869 measured reflections	intensity decay: 1%
1775 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.01	Δρ_max = 0.27 e Å⁻³
1775 reflections	Δρ_min = −0.30 e Å⁻³
127 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂O₃
M_r	192.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.944 (2), 11.143 (2), 7.4600 (15)
β (°)	100.69 (3)
V (Å³)	975.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.972, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	1869, 1775, 1166
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.174, 1.01
No. of reflections	1775
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.30

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+3/2.

Acknowledgements

This work was supported by the Science Fundamental Research Fund of the Education Department, Jiangsu Province (grant No. 06KJB150024). The authors thank the Center of Testing and Analysis, Nanjing University, for data collection.

References

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