PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1083.
Published online 2009 April 22. doi:  10.1107/S1600536809012276
PMCID: PMC2977762

2-Bromo-1-mesitylethanone

Abstract

In the mol­ecule of the title compound, C11H13BrO, the adjacent C atoms are almost coplanar with the aromatic ring [maximum deviation 0.035 (3) Å]. In the crystal structure, weak inter­molecular C—H(...)O inter­actions link the mol­ecules into chains along the b axis. A very weak C—H(...)π inter­action is also present.

Related literature

The title compound is used to synthesize organic electronic devices, see: Rose et al. (2008 [triangle]). For a related structure, see: Guss (1953 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1083-scheme1.jpg

Experimental

Crystal data

  • C11H13BrO
  • M r = 241.12
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1083-efi1.jpg
  • a = 15.379 (3) Å
  • b = 8.2820 (17) Å
  • c = 17.374 (4) Å
  • V = 2212.9 (8) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 3.68 mm−1
  • T = 294 K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.527, T max = 0.710
  • 3509 measured reflections
  • 2002 independent reflections
  • 805 reflections with I > 2σ(I)
  • R int = 0.099
  • 3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.095
  • S = 1.00
  • 2002 reflections
  • 118 parameters
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.29 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012276/hk2660sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012276/hk2660Isup2.hkl

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

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

supplementary crystallographic information

Comment

The title compound is used to synthesize organic electronic devices and medical intermediates (Rose et al., 2008). We report herein the crystal structure of the title compound, which is interested to us in the field.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C1-C6) is, of course, planar. Atoms C7, C8, C9 and C10 are -0.012 (2), -0.019 (3), -0.035 (3) and -0.006 (3) Å away from the ring plane of A, respectively.

In the crystal structure, weak intermolecular C-H···O interactions (Table 1) link the molecules into chains along the b axis, in which they may be effective in the stabilization of the structure. There also exists a weak C—H···π interaction (Table 1).

Experimental

The title compound, (m.p. 323-324 K), was prepared according to the literature method (Guss, 1953). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (0.2 g) in ethyl acetate (50 ml) and evaporating the solvent slowly at room temperature for about 3 d.

Refinement

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.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C11H13BrOF(000) = 976
Mr = 241.12Dx = 1.447 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 15.379 (3) Åθ = 10–13°
b = 8.2820 (17) ŵ = 3.68 mm1
c = 17.374 (4) ÅT = 294 K
V = 2212.9 (8) Å3Needle, colorless
Z = 80.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer805 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.099
graphiteθmax = 25.3°, θmin = 2.3°
ω/2θ scansh = 0→18
Absorption correction: ψ scan (North et al., 1968)k = 0→9
Tmin = 0.527, Tmax = 0.710l = −20→12
3509 measured reflections3 standard reflections every 120 min
2002 independent reflections intensity decay: 1%

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.022P)2] where P = (Fo2 + 2Fc2)/3
2002 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = −0.29 e Å3

Special details

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)

xyzUiso*/Ueq
Br0.22106 (4)0.01688 (8)0.59900 (4)0.0758 (3)
O0.1783 (3)−0.1396 (5)0.7510 (3)0.0853 (16)
C1−0.0250 (4)0.1475 (7)0.8818 (4)0.0557 (19)
H1A−0.08520.15830.88160.067*
C20.0138 (4)0.0860 (6)0.8160 (4)0.0461 (16)
C30.1038 (4)0.0675 (6)0.8208 (4)0.0458 (17)
C40.1509 (4)0.1135 (7)0.8840 (4)0.0462 (17)
C50.1083 (4)0.1744 (7)0.9464 (4)0.0540 (18)
H5A0.14000.20400.98980.065*
C60.0180 (5)0.1932 (7)0.9465 (4)0.062 (2)
C7−0.0290 (3)0.2598 (7)1.0151 (4)0.079 (2)
H7A−0.09030.26241.00480.119*
H7B−0.00880.36721.02550.119*
H7C−0.01810.19241.05900.119*
C8−0.0388 (3)0.0364 (6)0.7488 (3)0.0630 (18)
H8A−0.09890.06010.75830.094*
H8B−0.0319−0.07740.74030.094*
H8C−0.01960.09440.70400.094*
C90.2492 (3)0.0917 (7)0.8895 (3)0.068 (2)
H9A0.26920.13040.93850.101*
H9B0.27690.15170.84910.101*
H9C0.2633−0.02070.88430.101*
C100.1514 (4)−0.0002 (8)0.7513 (3)0.0459 (15)
C110.1681 (3)0.1137 (7)0.6882 (3)0.0592 (19)
H11A0.20570.19910.70690.071*
H11B0.11350.16280.67290.071*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br0.0835 (6)0.0705 (5)0.0734 (5)−0.0009 (5)0.0146 (4)−0.0066 (5)
O0.111 (4)0.057 (3)0.088 (4)0.040 (3)0.016 (3)0.015 (3)
C10.033 (4)0.044 (4)0.090 (6)0.000 (3)0.021 (4)0.011 (4)
C20.037 (5)0.036 (4)0.065 (5)0.002 (3)0.000 (4)−0.005 (4)
C30.044 (5)0.030 (4)0.064 (5)−0.002 (3)0.011 (4)−0.009 (3)
C40.026 (4)0.041 (4)0.072 (6)−0.004 (3)0.005 (4)0.001 (4)
C50.047 (5)0.050 (4)0.065 (5)−0.008 (4)−0.004 (4)0.002 (4)
C60.087 (7)0.039 (4)0.059 (6)−0.005 (5)0.016 (5)0.002 (4)
C70.075 (6)0.084 (5)0.079 (7)0.015 (4)0.011 (5)0.009 (5)
C80.049 (4)0.054 (4)0.085 (5)0.000 (4)−0.021 (4)0.002 (4)
C90.048 (5)0.080 (5)0.075 (5)−0.016 (3)−0.015 (4)0.014 (4)
C100.038 (4)0.038 (4)0.061 (4)−0.005 (4)−0.016 (3)0.010 (5)
C110.042 (4)0.065 (5)0.070 (5)0.002 (3)0.003 (4)0.003 (4)

Geometric parameters (Å, °)

Br—C111.925 (6)C6—C71.499 (8)
O—C101.226 (6)C7—H7A0.9600
C1—C61.358 (9)C7—H7B0.9600
C1—C21.387 (8)C7—H7C0.9600
C1—H1A0.9300C8—H8A0.9600
C2—C31.396 (7)C8—H8B0.9600
C2—C81.479 (7)C8—H8C0.9600
C3—C41.369 (8)C9—H9A0.9600
C3—C101.519 (8)C9—H9B0.9600
C4—C51.364 (7)C9—H9C0.9600
C4—C91.526 (7)C10—C111.470 (7)
C5—C61.399 (7)C11—H11A0.9700
C5—H5A0.9300C11—H11B0.9700
C6—C1—C2125.2 (6)H7B—C7—H7C109.5
C6—C1—H1A117.4C2—C8—H8A109.5
C2—C1—H1A117.4C2—C8—H8B109.5
C1—C2—C3114.7 (6)H8A—C8—H8B109.5
C1—C2—C8121.2 (6)C2—C8—H8C109.5
C3—C2—C8124.0 (6)H8A—C8—H8C109.5
C4—C3—C2122.8 (6)H8B—C8—H8C109.5
C4—C3—C10119.0 (6)C4—C9—H9A109.5
C2—C3—C10118.1 (6)C4—C9—H9B109.5
C5—C4—C3119.1 (6)H9A—C9—H9B109.5
C5—C4—C9118.0 (6)C4—C9—H9C109.5
C3—C4—C9122.8 (6)H9A—C9—H9C109.5
C4—C5—C6121.3 (6)H9B—C9—H9C109.5
C4—C5—H5A119.4O—C10—C11122.8 (6)
C6—C5—H5A119.4O—C10—C3120.9 (5)
C1—C6—C5116.8 (7)C11—C10—C3116.1 (6)
C1—C6—C7121.8 (7)C10—C11—Br114.0 (4)
C5—C6—C7121.4 (8)C10—C11—H11A108.7
C6—C7—H7A109.5Br—C11—H11A108.7
C6—C7—H7B109.5C10—C11—H11B108.7
H7A—C7—H7B109.5Br—C11—H11B108.7
C6—C7—H7C109.5H11A—C11—H11B107.6
H7A—C7—H7C109.5
C6—C1—C2—C32.1 (9)C9—C4—C5—C6−178.0 (5)
C6—C1—C2—C8178.8 (6)C2—C1—C6—C5−0.8 (10)
C1—C2—C3—C4−3.0 (8)C2—C1—C6—C7179.6 (6)
C8—C2—C3—C4−179.6 (6)C4—C5—C6—C10.2 (9)
C1—C2—C3—C10179.6 (5)C4—C5—C6—C7179.9 (6)
C8—C2—C3—C103.0 (8)C4—C3—C10—O77.5 (8)
C2—C3—C4—C52.6 (9)C2—C3—C10—O−105.0 (7)
C10—C3—C4—C5180.0 (5)C4—C3—C10—C11−98.3 (6)
C2—C3—C4—C9179.4 (5)C2—C3—C10—C1179.2 (7)
C10—C3—C4—C9−3.3 (8)O—C10—C11—Br8.5 (8)
C3—C4—C5—C6−1.2 (9)C3—C10—C11—Br−175.8 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9—H9B···Oi0.962.523.462 (7)166
C11—H11A···Oi0.972.363.308 (7)167
C7—H7C···Cg1ii0.962.943.722 (3)140

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2660).

References

  • 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.
  • Enraf–Nonius (1985). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Guss, C. O. (1953). J. Am. Chem. Soc.75, 3177–3179.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Rose, J. M., Deplace, F., Lynd, N. A., Wang, Z., Hotta, A., Lobkovsky, E. B., Edward, J., Kramer, E. K. & Coates, G. W. (2008). Macromolecules, 41, 9548–9555.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography