Acta Cryst. (2011). E67, o461 [ doi:10.1107/S1600536810054632 ]
In the title compound, C10H11ClO3, obtained by the reaction of 2,4-dihydroxyacetophenone, potassium carbonate and 1-bromo-2-chloroethane, an intramolecular O-H
O hydrogen bond occurs.
2, 4-Dihydroxylacetonephenone (5 mmol), potassium carbonate (6 mmol), 1-bromo-2-chloroethane (5 mmol), and 50 ml acetone were mixed in 100 ml flask. After 2.5 h stirring at 329 K, the crude product was obtained. The crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the title compound in n-hexane/ethyl acetate/methanol (3:3:1, V/V) at 283 K.
The positions of all H atoms were fixed geometrically and distance to H atoms were set by the program, with C—H distance in the range 0.93–0.97 Å and O—H distance of 0.82 Å, and refined as riding, with Uiso(H)= 1.2–1.5Ueq(C,O).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).
![[Figure 1]](./jh2251fig1thm.gif)
| Fig. 1. The molecular structure of (I), with atom labels and displacement ellipsoids drawn at the 30% probability level. |
| C10H11ClO3 | Dx = 1.442 Mg m−3 |
| Mr = 214.64 | Melting point = 375–376 K |
| Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.9970 (7) Å | Cell parameters from 1122 reflections |
| b = 5.3258 (4) Å | θ = 3.8–21.7° |
| c = 20.6307 (17) Å | µ = 0.36 mm−1 |
| V = 988.55 (13) Å3 | T = 298 K |
| Z = 4 | Orthorhombic, colourless |
| F(000) = 448 | 0.40 × 0.39 × 0.20 mm |
| Siemens SMART CCD area-detector diffractometer | 1664 independent reflections |
| Radiation source: fine-focus sealed tube | 1121 reflections with I > 2σ(I) |
| graphite | Rint = 0.063 |
| phi and ω scans | θmax = 25.0°, θmin = 3.8° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→8 |
| Tmin = 0.868, Tmax = 0.931 | k = −6→6 |
| 4434 measured reflections | l = −24→20 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
| wR(F2) = 0.141 | w = 1/[σ2(Fo2) + (0.0604P)2 + 0.0181P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max < 0.001 |
| 1664 reflections | Δρmax = 0.24 e Å−3 |
| 127 parameters | Δρmin = −0.21 e Å−3 |
| 1 restraint | Absolute structure: Flack (1983), 758 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.10 (14) |
| C10H11ClO3 | V = 988.55 (13) Å3 |
| Mr = 214.64 | Z = 4 |
| Orthorhombic, Pca21 | Mo Kα radiation |
| a = 8.9970 (7) Å | µ = 0.36 mm−1 |
| b = 5.3258 (4) Å | T = 298 K |
| c = 20.6307 (17) Å | 0.40 × 0.39 × 0.20 mm |
| Siemens SMART CCD area-detector diffractometer | 1664 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1121 reflections with I > 2σ(I) |
| Tmin = 0.868, Tmax = 0.931 | Rint = 0.063 |
| 4434 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
| wR(F2) = 0.141 | Δρmax = 0.24 e Å−3 |
| S = 1.07 | Δρmin = −0.21 e Å−3 |
| 1664 reflections | Absolute structure: Flack (1983), 758 Friedel pairs |
| 127 parameters | Flack parameter: 0.10 (14) |
| 1 restraint |
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 | ||
| Cl1 | −0.15098 (17) | 0.8043 (3) | 0.62958 (8) | 0.0704 (5) | |
| O1 | 0.2660 (4) | 0.6840 (7) | 1.02143 (16) | 0.0554 (10) | |
| O2 | 0.1105 (4) | 0.4294 (7) | 0.94300 (15) | 0.0518 (9) | |
| H2 | 0.1390 | 0.4778 | 0.9786 | 0.078* | |
| O3 | 0.1071 (4) | 0.6890 (7) | 0.72354 (16) | 0.0560 (10) | |
| C1 | 0.4075 (6) | 1.0330 (9) | 0.9931 (3) | 0.0535 (14) | |
| H1A | 0.4253 | 1.0346 | 1.0390 | 0.080* | |
| H1B | 0.3628 | 1.1890 | 0.9803 | 0.080* | |
| H1C | 0.5000 | 1.0116 | 0.9706 | 0.080* | |
| C2 | 0.3071 (5) | 0.8247 (9) | 0.9769 (2) | 0.0399 (11) | |
| C3 | 0.2555 (5) | 0.7861 (9) | 0.9118 (2) | 0.0387 (11) | |
| C4 | 0.1582 (5) | 0.5869 (9) | 0.8976 (2) | 0.0384 (11) | |
| C5 | 0.1058 (5) | 0.5501 (9) | 0.8351 (2) | 0.0414 (12) | |
| H5 | 0.0405 | 0.4190 | 0.8265 | 0.050* | |
| C6 | 0.1495 (5) | 0.7049 (9) | 0.7863 (2) | 0.0401 (12) | |
| C7 | 0.2485 (6) | 0.9076 (9) | 0.7991 (3) | 0.0480 (13) | |
| H7 | 0.2794 | 1.0143 | 0.7660 | 0.058* | |
| C8 | 0.2962 (5) | 0.9404 (9) | 0.8603 (2) | 0.0451 (13) | |
| H8 | 0.3599 | 1.0739 | 0.8687 | 0.054* | |
| C9 | 0.0041 (6) | 0.4949 (9) | 0.7074 (2) | 0.0518 (13) | |
| H9A | −0.0826 | 0.5050 | 0.7352 | 0.062* | |
| H9B | 0.0499 | 0.3316 | 0.7133 | 0.062* | |
| C10 | −0.0399 (6) | 0.5287 (9) | 0.6389 (3) | 0.0571 (14) | |
| H10A | −0.0957 | 0.3831 | 0.6245 | 0.068* | |
| H10B | 0.0484 | 0.5425 | 0.6122 | 0.068* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0739 (9) | 0.0668 (9) | 0.0706 (9) | 0.0068 (7) | −0.0081 (8) | 0.0050 (10) |
| O1 | 0.065 (2) | 0.055 (2) | 0.046 (2) | −0.009 (2) | −0.0029 (19) | 0.0086 (19) |
| O2 | 0.062 (2) | 0.046 (2) | 0.0474 (19) | −0.0151 (18) | −0.0008 (16) | 0.0123 (17) |
| O3 | 0.061 (2) | 0.063 (2) | 0.044 (2) | −0.0216 (19) | −0.0055 (16) | 0.0038 (19) |
| C1 | 0.049 (3) | 0.051 (3) | 0.061 (3) | 0.002 (3) | −0.008 (3) | −0.007 (3) |
| C2 | 0.032 (2) | 0.044 (3) | 0.044 (3) | 0.010 (2) | 0.003 (2) | −0.004 (3) |
| C3 | 0.033 (2) | 0.039 (3) | 0.044 (3) | 0.001 (2) | 0.007 (2) | 0.003 (2) |
| C4 | 0.039 (3) | 0.038 (3) | 0.039 (3) | 0.009 (2) | 0.003 (2) | 0.006 (2) |
| C5 | 0.046 (3) | 0.032 (3) | 0.046 (3) | −0.003 (2) | 0.001 (2) | 0.003 (2) |
| C6 | 0.045 (3) | 0.039 (3) | 0.036 (3) | −0.001 (2) | 0.002 (2) | −0.005 (2) |
| C7 | 0.050 (3) | 0.038 (3) | 0.056 (3) | −0.011 (2) | 0.007 (3) | 0.011 (3) |
| C8 | 0.043 (3) | 0.040 (3) | 0.052 (3) | −0.008 (2) | 0.000 (2) | −0.002 (2) |
| C9 | 0.053 (3) | 0.048 (3) | 0.055 (3) | −0.003 (3) | −0.005 (3) | −0.001 (2) |
| C10 | 0.062 (3) | 0.055 (3) | 0.055 (3) | 0.002 (3) | −0.001 (3) | −0.014 (3) |
| Cl1—C10 | 1.787 (5) | C4—C5 | 1.387 (7) |
| O1—C2 | 1.242 (6) | C5—C6 | 1.359 (6) |
| O2—C4 | 1.329 (5) | C5—H5 | 0.9300 |
| O2—H2 | 0.8200 | C6—C7 | 1.425 (6) |
| O3—C6 | 1.352 (6) | C7—C8 | 1.344 (7) |
| O3—C9 | 1.428 (6) | C7—H7 | 0.9300 |
| C1—C2 | 1.469 (7) | C8—H8 | 0.9300 |
| C1—H1A | 0.9600 | C9—C10 | 1.477 (8) |
| C1—H1B | 0.9600 | C9—H9A | 0.9700 |
| C1—H1C | 0.9600 | C9—H9B | 0.9700 |
| C2—C3 | 1.436 (7) | C10—H10A | 0.9700 |
| C3—C8 | 1.392 (7) | C10—H10B | 0.9700 |
| C3—C4 | 1.407 (7) | ||
| C4—O2—H2 | 109.5 | O3—C6—C7 | 113.7 (4) |
| C6—O3—C9 | 116.9 (4) | C5—C6—C7 | 120.2 (4) |
| C2—C1—H1A | 109.5 | C8—C7—C6 | 118.2 (5) |
| C2—C1—H1B | 109.5 | C8—C7—H7 | 120.9 |
| H1A—C1—H1B | 109.5 | C6—C7—H7 | 120.9 |
| C2—C1—H1C | 109.5 | C7—C8—C3 | 123.8 (5) |
| H1A—C1—H1C | 109.5 | C7—C8—H8 | 118.1 |
| H1B—C1—H1C | 109.5 | C3—C8—H8 | 118.1 |
| O1—C2—C3 | 120.6 (4) | O3—C9—C10 | 108.0 (4) |
| O1—C2—C1 | 118.1 (4) | O3—C9—H9A | 110.1 |
| C3—C2—C1 | 121.3 (5) | C10—C9—H9A | 110.1 |
| C8—C3—C4 | 116.7 (4) | O3—C9—H9B | 110.1 |
| C8—C3—C2 | 123.0 (5) | C10—C9—H9B | 110.1 |
| C4—C3—C2 | 120.3 (4) | H9A—C9—H9B | 108.4 |
| O2—C4—C5 | 117.2 (4) | C9—C10—Cl1 | 110.7 (4) |
| O2—C4—C3 | 122.0 (4) | C9—C10—H10A | 109.5 |
| C5—C4—C3 | 120.8 (4) | Cl1—C10—H10A | 109.5 |
| C6—C5—C4 | 120.3 (4) | C9—C10—H10B | 109.5 |
| C6—C5—H5 | 119.8 | Cl1—C10—H10B | 109.5 |
| C4—C5—H5 | 119.8 | H10A—C10—H10B | 108.1 |
| O3—C6—C5 | 126.1 (4) | ||
| O1—C2—C3—C8 | 179.0 (4) | C9—O3—C6—C7 | −178.1 (4) |
| C1—C2—C3—C8 | 0.0 (7) | C4—C5—C6—O3 | 179.8 (4) |
| O1—C2—C3—C4 | −0.4 (7) | C4—C5—C6—C7 | −0.5 (7) |
| C1—C2—C3—C4 | −179.3 (4) | O3—C6—C7—C8 | 179.5 (4) |
| C8—C3—C4—O2 | −179.2 (4) | C5—C6—C7—C8 | −0.2 (7) |
| C2—C3—C4—O2 | 0.2 (6) | C6—C7—C8—C3 | 0.7 (7) |
| C8—C3—C4—C5 | −0.4 (6) | C4—C3—C8—C7 | −0.4 (7) |
| C2—C3—C4—C5 | 179.0 (4) | C2—C3—C8—C7 | −179.7 (4) |
| O2—C4—C5—C6 | 179.7 (4) | C6—O3—C9—C10 | 173.7 (4) |
| C3—C4—C5—C6 | 0.8 (7) | O3—C9—C10—Cl1 | −69.2 (5) |
| C9—O3—C6—C5 | 1.6 (7) |
We would like to acknowledge funding support from the National Natural Science Foundation of China (grant No. 31070444).
Dermer, O. C. (1934). Chem. Rev. 14, 385–430.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Schlemper, E. O. (1986). Acta Cryst. C42, 755–757.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA.
In this paper, we used the Williamson reaction (Dermer, 1934) to form the title compound, (I), which was synthesized by the reaction of 2,4-dihydroxyacetophenone, potassium carbonate and 1-bromo-2-chloroethane at 329 K. In (I)(Fig.1), the bond lengths and angles are normal and comparable to those observed in the related structure (Schlemper, 1986). The dihedral angle between the benzene ring C3—C8 and the plane O3C9C10 is 5.83 (4)°. There are no significantly short intermolecular contacts in the crystal lattice.