Abstract
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 ▶, 2005 ▶); Hibbs et al. (2003 ▶); Huang et al. (2004 ▶); Ng (2007 ▶); Xu et al. (2005 ▶).
Experimental
Crystal data
C8H7FO2
M r = 154.14
Monoclinic,
a = 3.7978 (1) Å
b = 14.2421 (3) Å
c = 13.0092 (3) Å
β = 91.884 (2)°
V = 703.27 (3) Å3
Z = 4
Mo Kα radiation
μ = 0.12 mm−1
T = 100 (2) K
0.16 × 0.14 × 0.12 mm
Data collection
Bruker SMART APEX diffractometer
Absorption correction: none
8762 measured reflections
1601 independent reflections
1224 reflections with I > 2σ(I)
R int = 0.039
Refinement
R[F 2 > 2σ(F 2)] = 0.043
wR(F 2) = 0.127
S = 1.05
1601 reflections
128 parameters
7 restraints
All H-atom parameters refined
Δρmax = 0.30 e Å−3
Δρmin = −0.28 e Å−3
Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: 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 ▶).
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011173/lh2605sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011173/lh2605Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Hydrogen-bond geometry (Å, °).
| 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) |
Acknowledgments
We thank the University of Malaya for the purchase of the diffractometer.
supplementary crystallographic information
Comment
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.
Experimental
The compound was purchased from Aldrich Chemical Company; the chemical exists as prismatic crystals.
Refinement
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.
Figures
Fig. 1.
70% Probability thermal ellipsoid plot of 4'-fluoro-2'-hydroxyacetophenone. Hydrogen atoms are drawn as spheres of arbitrary radius.
Crystal data
| C8H7FO2 | F000 = 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 = 2.9–26.4º |
| b = 14.2421 (3) Å | µ = 0.12 mm−1 |
| c = 13.0092 (3) Å | T = 100 (2) K |
| β = 91.884 (2)º | Prism, colorless |
| V = 703.27 (3) Å3 | 0.16 × 0.14 × 0.12 mm |
| Z = 4 |
Data collection
| Bruker SMART APEXII diffractometer | 1224 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.039 |
| Monochromator: graphite | θmax = 27.5º |
| T = 100(2) K | θmin = 2.1º |
| ω scans | h = −4→4 |
| Absorption correction: none | k = −18→18 |
| 8762 measured reflections | l = −16→16 |
| 1601 independent reflections |
Refinement
| 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)] = 0.043 | All H-atom parameters refined |
| wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0775P)2 + 0.0798P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max = 0.001 |
| 1601 reflections | Δρmax = 0.30 e Å−3 |
| 128 parameters | Δρmin = −0.28 e Å−3 |
| 7 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| 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)* |
Atomic displacement parameters (Å2)
| 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) |
Geometric parameters (Å, °)
| 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) |
Hydrogen-bond geometry (Å, °)
| 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) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2605).
References
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- Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
- Filarowski, A., Kochel, A., Cieslik, K. & Koll, A. (2005). J. Phys. Org. Chem.18, 986–993.
- Filarowski, A., Koll, A., Kochel, A., Kalenik, J. & Hansen, P. E. (2004). J. Mol. Struct.700, 67–72.
- Hibbs, D. E., Overgaard, J. & Piltz, R. O. (2003). Org. Biomol. Chem.1, 1191–1198. [DOI] [PubMed]
- Huang, H.-R., Xia, X.-K., She, Z.-G., Lin, Y.-C., Vrijmoed, L. L. P. & Jones, E. B. G. (2004). Acta Cryst. E60, o2509–o2510.
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- Westrip, S. P. (2008). publCIF In preparation.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011173/lh2605sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011173/lh2605Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report