organic compounds
4′-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, 2005); Hibbs et al. (2003); Huang et al. (2004); Ng (2007); Xu et al. (2005).
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
10.1107/S1600536808011173/lh2605sup1.cif
contains datablocks global, I. DOI: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).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
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Filarowski, A., Kochel, A., Cieslik, K. & Koll, A. (2005). J. Phys. Org. Chem. 18, 986–993. Web of Science CSD CrossRef CAS Google Scholar
Filarowski, A., Koll, A., Kochel, A., Kalenik, J. & Hansen, P. E. (2004). J. Mol. Struct. 700, 67–72. Web of Science CSD CrossRef CAS Google Scholar
Hibbs, D. E., Overgaard, J. & Piltz, R. O. (2003). Org. Biomol. Chem. 1, 1191–1198. Web of Science CSD CrossRef PubMed CAS Google Scholar
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. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ng, S. W. (2007). Acta Cryst. E63, o1805–o1806. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
Xu, X.-Y., Gao, J., Chen, J., Li, S.-Z., Yang, X.-J. & Song, H.-B. (2005). Chin. J. Struct. Chem. 24, 436–438. CAS Google Scholar
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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.