organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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[Nichols, D. E. (1986). J. Psychoactive Drugs, 18, 305-313.]). For a related structure, see: Zhu (2003[Zhu, Z. F. (2003). Huaxue Yanjiu Yu Yingyong, 15, 417-418.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12O3

  • Mr = 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[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.972, Tmax = 0.991

  • 1869 measured reflections

  • 1775 independent reflections

  • 1166 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft. The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON.

Supporting information


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.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

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
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.
[Figure 2] 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
C11H12O3F(000) = 408
Mr = 192.21Dx = 1.309 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 11.944 (2) Åθ = 9–12°
b = 11.143 (2) ŵ = 0.10 mm1
c = 7.4600 (15) ÅT = 298 K
β = 100.69 (3)°Block, colourless
V = 975.6 (3) Å30.30 × 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 tubeRint = 0.045
Graphite monochromatorθmax = 25.3°, θmin = 1.7°
ω/2θ scansh = 014
Absorption correction: ψ scan
(North et al., 1968)
k = 013
Tmin = 0.972, Tmax = 0.991l = 88
1869 measured reflections3 standard reflections every 120 min
1775 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.05P)2 + 2.1P]
where P = (Fo2 + 2Fc2)/3
1775 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C11H12O3V = 975.6 (3) Å3
Mr = 192.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.944 (2) ŵ = 0.10 mm1
b = 11.143 (2) ÅT = 298 K
c = 7.4600 (15) Å0.30 × 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)
Rint = 0.045
Tmin = 0.972, Tmax = 0.9913 standard reflections every 120 min
1869 measured reflections intensity decay: 1%
1775 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0700 restraints
wR(F2) = 0.174H-atom parameters constrained
S = 1.01Δρmax = 0.27 e Å3
1775 reflectionsΔρmin = 0.30 e Å3
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
xyzUiso*/Ueq
O10.4098 (2)0.2566 (2)0.9257 (3)0.0479 (7)
O20.8478 (2)0.2368 (2)1.0244 (4)0.0521 (7)
O30.8912 (2)0.0624 (2)0.8880 (3)0.0475 (7)
C10.1275 (3)0.0544 (4)0.6397 (6)0.0625 (12)
H1A0.05520.09300.63440.094*
H1B0.12860.01980.70550.094*
H1C0.13940.03840.51810.094*
C20.2211 (3)0.1353 (3)0.7358 (6)0.0486 (10)
H2A0.21720.21100.67080.058*
H2B0.20750.15180.85760.058*
C30.3397 (3)0.0849 (3)0.7510 (4)0.0347 (8)
H3A0.35430.06980.62930.042*
H3B0.34370.00860.81450.042*
C40.4319 (3)0.1669 (3)0.8506 (4)0.0284 (7)
C50.5527 (2)0.1323 (3)0.8527 (4)0.0268 (7)
C60.6389 (3)0.2119 (3)0.9436 (4)0.0303 (7)
H6A0.62110.28191.00020.036*
C70.7489 (3)0.1792 (3)0.9424 (4)0.0362 (8)
C80.7769 (3)0.0757 (3)0.8658 (4)0.0342 (8)
C90.6943 (3)0.0028 (3)0.7756 (4)0.0332 (8)
H9A0.71360.07220.71900.040*
C100.5818 (3)0.0280 (3)0.7748 (4)0.0301 (7)
H10A0.52430.02350.71990.036*
C110.9378 (3)0.1710 (3)0.9731 (6)0.0503 (10)
H11A0.99520.15281.07960.060*
H11B0.97310.21750.88870.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0483 (15)0.0414 (15)0.0506 (16)0.0091 (11)0.0003 (12)0.0123 (13)
O20.0351 (13)0.0524 (16)0.0651 (18)0.0039 (12)0.0004 (12)0.0165 (14)
O30.0378 (14)0.0530 (16)0.0520 (16)0.0046 (11)0.0089 (11)0.0057 (13)
C10.039 (2)0.078 (3)0.066 (3)0.006 (2)0.0016 (19)0.017 (2)
C20.048 (2)0.041 (2)0.053 (2)0.0024 (17)0.0016 (17)0.0038 (18)
C30.0429 (19)0.0340 (18)0.0241 (17)0.0047 (14)0.0021 (14)0.0017 (14)
C40.0428 (18)0.0209 (15)0.0211 (15)0.0085 (13)0.0051 (13)0.0006 (13)
C50.0310 (16)0.0301 (17)0.0180 (15)0.0011 (13)0.0015 (12)0.0033 (13)
C60.0362 (17)0.0267 (16)0.0292 (17)0.0033 (13)0.0095 (13)0.0073 (13)
C70.0361 (18)0.0399 (19)0.0306 (18)0.0056 (15)0.0016 (14)0.0005 (15)
C80.0432 (19)0.0326 (18)0.0262 (17)0.0066 (14)0.0043 (14)0.0014 (14)
C90.0402 (19)0.0294 (17)0.0309 (17)0.0037 (14)0.0093 (14)0.0076 (14)
C100.0425 (19)0.0259 (16)0.0207 (15)0.0017 (13)0.0030 (13)0.0028 (13)
C110.041 (2)0.053 (2)0.057 (2)0.0099 (18)0.0085 (17)0.004 (2)
Geometric parameters (Å, º) top
O1—C41.200 (4)C3—H3B0.9700
O2—C71.384 (4)C4—C51.491 (4)
O2—C111.410 (4)C5—C101.372 (4)
O3—C81.353 (4)C5—C61.432 (4)
O3—C111.431 (4)C6—C71.364 (4)
C1—C21.510 (5)C6—H6A0.9300
C1—H1A0.9600C7—C81.356 (5)
C1—H1B0.9600C8—C91.395 (4)
C1—H1C0.9600C9—C101.385 (4)
C2—C31.508 (5)C9—H9A0.9300
C2—H2A0.9700C10—H10A0.9300
C2—H2B0.9700C11—H11A0.9700
C3—C41.515 (4)C11—H11B0.9700
C3—H3A0.9700
C7—O2—C11105.7 (3)C10—C5—C4122.4 (3)
C8—O3—C11105.2 (3)C6—C5—C4117.0 (3)
C2—C1—H1A109.5C7—C6—C5116.1 (3)
C2—C1—H1B109.5C7—C6—H6A122.0
H1A—C1—H1B109.5C5—C6—H6A122.0
C2—C1—H1C109.5C8—C7—C6122.9 (3)
H1A—C1—H1C109.5C8—C7—O2108.9 (3)
H1B—C1—H1C109.5C6—C7—O2128.1 (3)
C3—C2—C1114.6 (3)O3—C8—C7111.3 (3)
C3—C2—H2A108.6O3—C8—C9126.7 (3)
C1—C2—H2A108.6C7—C8—C9121.9 (3)
C3—C2—H2B108.6C10—C9—C8116.4 (3)
C1—C2—H2B108.6C10—C9—H9A121.8
H2A—C2—H2B107.6C8—C9—H9A121.8
C2—C3—C4113.5 (3)C5—C10—C9122.0 (3)
C2—C3—H3A108.9C5—C10—H10A119.0
C4—C3—H3A108.9C9—C10—H10A119.0
C2—C3—H3B108.9O2—C11—O3107.9 (3)
C4—C3—H3B108.9O2—C11—H11A110.1
H3A—C3—H3B107.7O3—C11—H11A110.1
O1—C4—C5120.5 (3)O2—C11—H11B110.1
O1—C4—C3121.9 (3)O3—C11—H11B110.1
C5—C4—C3117.6 (3)H11A—C11—H11B108.4
C10—C5—C6120.6 (3)
C1—C2—C3—C4179.1 (3)C11—O3—C8—C74.7 (4)
C2—C3—C4—O17.5 (5)C11—O3—C8—C9174.6 (3)
C2—C3—C4—C5172.6 (3)C6—C7—C8—O3178.0 (3)
O1—C4—C5—C10177.3 (3)O2—C7—C8—O31.8 (4)
C3—C4—C5—C102.6 (4)C6—C7—C8—C92.7 (5)
O1—C4—C5—C61.5 (4)O2—C7—C8—C9178.9 (3)
C3—C4—C5—C6178.6 (3)O3—C8—C9—C10178.2 (3)
C10—C5—C6—C71.8 (4)C7—C8—C9—C102.6 (5)
C4—C5—C6—C7179.4 (3)C6—C5—C10—C92.0 (5)
C5—C6—C7—C82.2 (5)C4—C5—C10—C9179.3 (3)
C5—C6—C7—O2177.6 (3)C8—C9—C10—C52.3 (5)
C11—O2—C7—C87.6 (4)C7—O2—C11—O310.4 (4)
C11—O2—C7—C6176.5 (4)C8—O3—C11—O29.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O1i0.932.533.209 (4)130
Symmetry code: (i) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC11H12O3
Mr192.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)11.944 (2), 11.143 (2), 7.4600 (15)
β (°) 100.69 (3)
V3)975.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.972, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
1869, 1775, 1166
Rint0.045
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.174, 1.01
No. of reflections1775
No. of parameters127
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C9—H9A···O1i0.932.533.209 (4)130
Symmetry code: (i) x+1, y1/2, 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

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationEnraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft. The Netherlands.  Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationNichols, D. E. (1986). J. Psychoactive Drugs, 18, 305–313.  CrossRef CAS PubMed Web of Science Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhu, Z. F. (2003). Huaxue Yanjiu Yu Yingyong, 15, 417–418.  CAS Google Scholar

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