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organic compounds
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access4′-Fluoro-2′-hydroxyacetophenone
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The title compound, C8H7FO2, crystallizes as discrete molecules, the conformation of which may be influenced by an intramolecular hydroxy–carbonyl O—H⋯O hydrogen bond.
Related literature
For the crystal structures of other substituted acetophenones, see: Filarowski et al. (2004![[Filarowski, A., Koll, A., Kochel, A., Kalenik, J. & Hansen, P. E. (2004). J. Mol. Struct. 700, 67-72.]](../../../../../../logos/arrows/e_arr.gif "Filarowski, A., Koll, A., Kochel, A., Kalenik, J. & Hansen, P. E. (2004). J. Mol. Struct. 700, 67-72.")
, 2005); Hibbs et al. (2003); Huang et al. (2004); Ng (2007); Xu et al. (2005).
![[Scheme 1]](lh2605scheme1.gif)
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536808011173/lh2605sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536808011173/lh2605Isup2.hkl
The compound was purchased from Aldrich Chemical Company; the chemical exists as prismatic crystals.
All H-atoms were located in a difference Fourier map, and were refined with distance restraints of C—H 0.99±0.01 Å and O–H 0.84±0.01 Å. Their temperature factors were freely refined.
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
![[Figure 1]](./lh2605fig1thm.gif) | Fig. 1. 70% Probability thermal ellipsoid plot of 4'-fluoro-2'-hydroxyacetophenone. Hydrogen atoms are drawn as spheres of arbitrary radius. |
| C8H7FO2 | F(000) = 320 |
| Mr = 154.14 | Dx = 1.456 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 1854 reflections |
| a = 3.7978 (1) Å | θ = 2.9–26.4° |
| b = 14.2421 (3) Å | µ = 0.12 mm−1 |
| c = 13.0092 (3) Å | T = 100 K |
| β = 91.884 (2)° | Prism, colorless |
| V = 703.27 (3) Å3 | 0.16 × 0.14 × 0.12 mm |
| Z = 4 |
| Bruker SMART APEXII diffractometer | 1224 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.039 |
| Graphite monochromator | θmax = 27.5°, θmin = 2.1° |
| ω scans | h = −4→4 |
| 8762 measured reflections | k = −18→18 |
| 1601 independent reflections | l = −16→16 |
| 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.127 | All H-atom parameters refined |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0775P)2 + 0.0798P] where P = (Fo2 + 2Fc2)/3 |
| 1601 reflections | (Δ/σ)max = 0.001 |
| 128 parameters | Δρmax = 0.30 e Å−3 |
| 7 restraints | Δρmin = −0.28 e Å−3 |
| C8H7FO2 | V = 703.27 (3) Å3 |
| Mr = 154.14 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 3.7978 (1) Å | µ = 0.12 mm−1 |
| b = 14.2421 (3) Å | T = 100 K |
| c = 13.0092 (3) Å | 0.16 × 0.14 × 0.12 mm |
| β = 91.884 (2)° |
| Bruker SMART APEXII diffractometer | 1224 reflections with I > 2σ(I) |
| 8762 measured reflections | Rint = 0.039 |
| 1601 independent reflections |
| R[F2 > 2σ(F2)] = 0.043 | 7 restraints |
| wR(F2) = 0.127 | All H-atom parameters refined |
| S = 1.05 | Δρmax = 0.30 e Å−3 |
| 1601 reflections | Δρmin = −0.28 e Å−3 |
| 128 parameters |
| x | y | z | Uiso*/Ueq | ||
| F1 | 0.1828 (3) | 0.50469 (6) | 0.65495 (7) | 0.0319 (3) | |
| O1 | 0.4466 (3) | 0.72547 (8) | 0.40329 (8) | 0.0325 (3) | |
| O2 | 0.7055 (3) | 0.88271 (8) | 0.46250 (8) | 0.0320 (3) | |
| C1 | 0.5542 (4) | 0.76649 (10) | 0.58170 (11) | 0.0196 (3) | |
| C2 | 0.4380 (4) | 0.70349 (10) | 0.50349 (11) | 0.0211 (3) | |
| C3 | 0.3106 (4) | 0.61483 (10) | 0.52868 (11) | 0.0229 (3) | |
| C4 | 0.3051 (4) | 0.59128 (10) | 0.63045 (12) | 0.0225 (4) | |
| C5 | 0.4165 (4) | 0.64954 (10) | 0.71015 (11) | 0.0235 (4) | |
| C6 | 0.5398 (4) | 0.73716 (10) | 0.68410 (11) | 0.0216 (4) | |
| C7 | 0.6909 (4) | 0.85914 (10) | 0.55377 (11) | 0.0227 (4) | |
| C8 | 0.8132 (5) | 0.92675 (11) | 0.63595 (12) | 0.0267 (4) | |
| H1 | 0.519 (6) | 0.7824 (9) | 0.4037 (19) | 0.066 (8)* | |
| H3 | 0.221 (5) | 0.5733 (10) | 0.4729 (11) | 0.029 (5)* | |
| H5 | 0.412 (5) | 0.6279 (11) | 0.7807 (8) | 0.023 (4)* | |
| H6 | 0.616 (4) | 0.7801 (10) | 0.7398 (10) | 0.024 (4)* | |
| H81 | 0.602 (4) | 0.9492 (14) | 0.6716 (15) | 0.051 (6)* | |
| H82 | 0.968 (4) | 0.8980 (12) | 0.6899 (12) | 0.033 (5)* | |
| H83 | 0.937 (5) | 0.9790 (11) | 0.6047 (15) | 0.044 (5)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| F1 | 0.0427 (6) | 0.0200 (5) | 0.0331 (5) | −0.0081 (4) | 0.0043 (4) | 0.0043 (4) |
| O1 | 0.0514 (8) | 0.0275 (6) | 0.0182 (6) | −0.0115 (6) | −0.0021 (5) | 0.0018 (4) |
| O2 | 0.0457 (8) | 0.0252 (6) | 0.0254 (6) | −0.0091 (5) | 0.0038 (5) | 0.0027 (4) |
| C1 | 0.0191 (8) | 0.0176 (7) | 0.0221 (7) | 0.0013 (5) | 0.0012 (6) | −0.0019 (5) |
| C2 | 0.0223 (8) | 0.0221 (8) | 0.0187 (7) | −0.0003 (6) | 0.0002 (6) | 0.0003 (5) |
| C3 | 0.0235 (8) | 0.0207 (7) | 0.0244 (8) | −0.0012 (6) | −0.0003 (6) | −0.0023 (6) |
| C4 | 0.0227 (8) | 0.0146 (7) | 0.0304 (8) | −0.0005 (6) | 0.0045 (6) | 0.0030 (6) |
| C5 | 0.0266 (9) | 0.0240 (8) | 0.0201 (7) | 0.0020 (6) | 0.0028 (6) | 0.0026 (6) |
| C6 | 0.0226 (8) | 0.0205 (7) | 0.0217 (7) | 0.0022 (6) | 0.0007 (6) | −0.0022 (5) |
| C7 | 0.0231 (8) | 0.0204 (7) | 0.0247 (8) | 0.0006 (6) | 0.0021 (6) | −0.0004 (6) |
| C8 | 0.0277 (9) | 0.0220 (8) | 0.0304 (8) | −0.0035 (6) | 0.0026 (7) | −0.0032 (6) |
| F1—C4 | 1.3594 (16) | C3—H3 | 0.988 (9) |
| O1—C2 | 1.3420 (17) | C4—C5 | 1.383 (2) |
| O1—H1 | 0.857 (10) | C5—C6 | 1.379 (2) |
| O2—C7 | 1.2370 (18) | C5—H5 | 0.969 (9) |
| C1—C6 | 1.399 (2) | C6—H6 | 0.984 (9) |
| C1—C2 | 1.416 (2) | C7—C8 | 1.501 (2) |
| C1—C7 | 1.468 (2) | C8—H81 | 0.993 (10) |
| C2—C3 | 1.395 (2) | C8—H82 | 0.989 (9) |
| C3—C4 | 1.367 (2) | C8—H83 | 0.977 (10) |
| C2—O1—H1 | 103.5 (17) | C6—C5—H5 | 122.5 (10) |
| C6—C1—C2 | 118.29 (13) | C4—C5—H5 | 120.3 (10) |
| C6—C1—C7 | 121.96 (13) | C5—C6—C1 | 121.90 (13) |
| C2—C1—C7 | 119.74 (13) | C5—C6—H6 | 118.4 (10) |
| O1—C2—C3 | 117.32 (13) | C1—C6—H6 | 119.7 (10) |
| O1—C2—C1 | 122.21 (13) | O2—C7—C1 | 120.59 (13) |
| C3—C2—C1 | 120.47 (13) | O2—C7—C8 | 119.14 (14) |
| C4—C3—C2 | 117.78 (14) | C1—C7—C8 | 120.27 (13) |
| C4—C3—H3 | 123.3 (11) | C7—C8—H81 | 107.6 (13) |
| C2—C3—H3 | 118.9 (10) | C7—C8—H82 | 113.7 (11) |
| F1—C4—C3 | 117.77 (13) | H81—C8—H82 | 105.8 (17) |
| F1—C4—C5 | 117.83 (13) | C7—C8—H83 | 109.5 (12) |
| C3—C4—C5 | 124.40 (14) | H81—C8—H83 | 111.0 (18) |
| C6—C5—C4 | 117.17 (13) | H82—C8—H83 | 109.2 (17) |
| C6—C1—C2—O1 | −179.20 (14) | C3—C4—C5—C6 | 0.2 (2) |
| C7—C1—C2—O1 | −0.3 (2) | C4—C5—C6—C1 | −0.3 (2) |
| C6—C1—C2—C3 | 0.4 (2) | C2—C1—C6—C5 | 0.0 (2) |
| C7—C1—C2—C3 | 179.37 (14) | C7—C1—C6—C5 | −178.94 (14) |
| O1—C2—C3—C4 | 179.15 (14) | C6—C1—C7—O2 | 178.92 (14) |
| C1—C2—C3—C4 | −0.5 (2) | C2—C1—C7—O2 | 0.0 (2) |
| C2—C3—C4—F1 | −179.64 (13) | C6—C1—C7—C8 | −1.4 (2) |
| C2—C3—C4—C5 | 0.2 (2) | C2—C1—C7—C8 | 179.68 (14) |
| F1—C4—C5—C6 | −179.97 (13) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2 | 0.86 (1) | 1.76 (1) | 2.554 (2) | 154 (2) |
Experimental details
| Crystal data | |
| Chemical formula | C8H7FO2 |
| Mr | 154.14 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 100 |
| a, b, c (Å) | 3.7978 (1), 14.2421 (3), 13.0092 (3) |
| β (°) | 91.884 (2) |
| V (Å3) | 703.27 (3) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.12 |
| Crystal size (mm) | 0.16 × 0.14 × 0.12 |
| Data collection | |
| Diffractometer | Bruker SMART APEXII diffractometer |
| Absorption correction | – |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 8762, 1601, 1224 |
| Rint | 0.039 |
| (sin θ/λ)max (Å−1) | 0.650 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.127, 1.05 |
| No. of reflections | 1601 |
| No. of parameters | 128 |
| No. of restraints | 7 |
| H-atom treatment | All H-atom parameters refined |
| Δρmax, Δρmin (e Å−3) | 0.30, −0.28 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2 | 0.857 (10) | 1.76 (1) | 2.554 (2) | 154 (2) |
Acknowledgements
We thank the University of Malaya for the purchase of the diffractometer.
References
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Acetopheonone is a liquid at room temperature. If a small substituent such as 5'-bromo (Ng, 2007), 5'-chloro (Filarowski et al., 2004), 6'-hydroxy (Huang et al., 2004), 5'-nitro (Hibbs et al., 2003), 4'-methoxy (Filarowski et al., 2005; Xu et al., 2005) or 6'-methoxy (Filarowski et al., 2005) is present the compounds exists as crystalline solids. The compound (I) containing the reltively smaller F substituent sublimes at room temperature. The structure contains discrete molecules (Fig. 1), in which the conformation may be influenced by an intramolecular hydrogen bond between the hydroxy and carbonyl groups.