organic compounds
(2Z,4E)-1-(5-Fluoro-2-hydroxyphenyl)-5-(4-fluorophenyl)-3-hydroxypenta-2,4-dien-1-one
aThe Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen 361005, People's Republic of China, bSchool of Pharmaceutical Sciences, Xiamen University, Sounth Xiang-An Road, Xiamen 361100, People's Republic of China, and cState Ocean Adm, Inst Oceanog 3, Xiamen 361005, People's Republic of China
*Correspondence e-mail: fangmj@xmu.edu.cn
In the title molecule, C17H12F2O3, the dihedral angle between the benzene rings is 8.6 (2)°. In the crystal, two pairs of O—H⋯O hydrogen bonds connect the molecules into inversion dimers. In addition, weak C—H⋯F hydrogen bonds link the dimers into a two-dimensional network parallel to (10-4). The carbonyl O atom is an acceptor for two weak intramolecular hydrogen bonds.
CCDC reference: 976529
Related literature
For the biological activities of et al. (2007); Schobert et al. (2009). For the synthesis, see: Baker (1933); Mahal & Venkataraman (1934). For a related structure, see: Fun et al. (2012).
see: MengExperimental
Crystal data
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 976529
https://doi.org/10.1107/S1600536813033564/lh5672sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033564/lh5672Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813033564/lh5672Isup3.cml
The reaction scheme is shown in Fig. 1. A reaction mixture of (E)-3-(4-fluorophenyl) acryloyl chloride (0.37 g, 2.0 mmol) and 1-(5-fluoro-2-hydroxyphenyl)ethanone (0.31 g, 2.0 mmol) in pyridine (10 ml) was stirred for 1 h at 323K (Baker et al., 1933). The mixture was then neutralized with dilute hydrochloric acid, and extracted with ethyl acetate (3×15 ml). The organic phase was concentrated under vacuum to obtain a slurry residue to which was added pyridine (10 ml) and potassium hydroxide (0.21 g, 1.5 mmol). The solution was stirred for 3 h at 323K. The mixture was then neutralized with dilute hydrochloric acid, and extracted with ethyl acetate (3×15 ml). The organic phase was dried over anhydrous MgSO4 and concentrated under vacuum to obtain a slurry residue. The residue was purified by
using petroleum ether and ethyl acetate (v:v=5:1) as to give a light yellow solid (Mahal & Venkataraman, 1934). Single crystals were obtained by crystallization of a petroleum ether and ethyl acetate (v:v=1:4) solution of the title compound.All H atoms were placed in geometrically idealized positions and treated as riding on their parent atoms, with C—H = 0.93 (aromatic) or 0.98 (CH), O—H = 0.82 Å and isotropic displacement parameters for were set at Uiso(H) = x Ueq (carried atom), with x = 1.5 for hydroxy, and x = 1.2 for methyne.
Dibenzoylmethane (1,3-Diphenyl-propane-1,3-dione, DBM) and 4) (Fig. 4). The oxygen atom of the –C═O group is an acceptor for two intramolecular hydrogen bonds (Fig. 2).
have been found to exhibit a variety of biological activities, such as anti-tumor, anti-inflammatory, antibacterial, anti-parasitic, anti-oxidation and anti-viral effect (Schobert et al., 2009; Meng et al., 2007). Recently, we carried out to synthesis a series of (E)-1,5-diphenylpent-4-ene-1,3-dione derivatives. These compounds have keto-enol however, the enol form predominates. The dihedral angle between the planes of the phenyl rings (C2–C7) and (C12–C17) is 8.6 (3) °. Bond lengths and angles in (I, Fig. 2) are agreement with values reported for a similar compound (Fun et al., 2012). In the crystal, two pairs of O—H···O hydrogen bonds connect the molecules into inversion dimers (Fig. 3). In addition, weak C—H···F hydrogen bonds link dimers into a two-dimensional network parallel to (10For the biological activities of
see: Meng et al. (2007); Schobert et al. (2009). For the synthesis, see: Baker (1933); Mahal & Venkataraman (1934). For a related structure, see: Fun et al. (2012).Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The reaction scheme. | |
Fig. 2. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level and H atoms drawn as small spheres of arbitrary radii. | |
Fig. 3. An inversion dimers of (I). Hydrogen bonds are shown as dashed lines. | |
Fig. 4. Part of the crystal structure with hydrogen bonds shown as dashed lines. |
C17H12F2O3 | F(000) = 624 |
Mr = 302.27 | Dx = 1.472 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2113 reflections |
a = 6.8275 (18) Å | θ = 1.6–27.3° |
b = 14.004 (4) Å | µ = 0.12 mm−1 |
c = 14.267 (4) Å | T = 173 K |
β = 91.293 (5)° | Block, yellow |
V = 1363.8 (7) Å3 | 0.32 × 0.23 × 0.18 mm |
Z = 4 |
Bruker APEX CCD diffractometer | 2392 independent reflections |
Radiation source: fine-focus sealed tube | 2040 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scan | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −8→8 |
Tmin = 0.963, Tmax = 0.979 | k = −16→16 |
6787 measured reflections | l = −12→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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.073P)2 + 0.3861P] where P = (Fo2 + 2Fc2)/3 |
2392 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C17H12F2O3 | V = 1363.8 (7) Å3 |
Mr = 302.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.8275 (18) Å | µ = 0.12 mm−1 |
b = 14.004 (4) Å | T = 173 K |
c = 14.267 (4) Å | 0.32 × 0.23 × 0.18 mm |
β = 91.293 (5)° |
Bruker APEX CCD diffractometer | 2392 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2040 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.979 | Rint = 0.028 |
6787 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.21 e Å−3 |
2392 reflections | Δρmin = −0.29 e Å−3 |
199 parameters |
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 | ||
F1 | −1.0830 (2) | 1.43310 (10) | 0.38367 (11) | 0.0579 (5) | |
F2 | −1.6953 (2) | 0.59884 (10) | 0.25050 (10) | 0.0577 (5) | |
O3 | −0.7476 (2) | 0.93089 (10) | 0.42390 (11) | 0.0383 (4) | |
H3A | −0.6598 | 0.9675 | 0.4404 | 0.057* | |
O2 | −0.5856 (2) | 1.09111 (10) | 0.45331 (11) | 0.0348 (4) | |
O1 | −0.3972 (2) | 1.24886 (10) | 0.46202 (11) | 0.0391 (4) | |
H1A | −0.4108 | 1.1908 | 0.4649 | 0.059* | |
C16 | −1.5714 (3) | 0.75182 (16) | 0.27847 (15) | 0.0371 (5) | |
H16A | −1.6915 | 0.7780 | 0.2602 | 0.045* | |
C6 | −0.9127 (3) | 1.38522 (15) | 0.40188 (16) | 0.0371 (5) | |
C9 | −0.9017 (3) | 0.98066 (14) | 0.39432 (13) | 0.0276 (5) | |
C1 | −0.7404 (3) | 1.13263 (14) | 0.42564 (13) | 0.0258 (5) | |
C7 | −0.9178 (3) | 1.28835 (15) | 0.40533 (15) | 0.0328 (5) | |
H7A | −1.0352 | 1.2559 | 0.3952 | 0.039* | |
C5 | −0.7442 (4) | 1.43672 (16) | 0.41622 (16) | 0.0401 (6) | |
H5A | −0.7455 | 1.5030 | 0.4127 | 0.048* | |
C13 | −1.2171 (3) | 0.67182 (15) | 0.33270 (14) | 0.0336 (5) | |
H13A | −1.0979 | 0.6447 | 0.3511 | 0.040* | |
C8 | −0.9043 (3) | 1.07757 (14) | 0.39450 (14) | 0.0287 (5) | |
H8A | −1.0170 | 1.1090 | 0.3736 | 0.034* | |
C3 | −0.5709 (3) | 1.28979 (15) | 0.44117 (14) | 0.0297 (5) | |
C14 | −1.3700 (4) | 0.61349 (16) | 0.30486 (16) | 0.0400 (6) | |
H14A | −1.3558 | 0.5474 | 0.3041 | 0.048* | |
C11 | −1.0733 (3) | 0.83020 (14) | 0.36333 (14) | 0.0287 (5) | |
H11A | −0.9613 | 0.7987 | 0.3852 | 0.034* | |
C2 | −0.7438 (3) | 1.23770 (14) | 0.42429 (13) | 0.0271 (5) | |
C17 | −1.4183 (3) | 0.80885 (16) | 0.30625 (15) | 0.0331 (5) | |
H17A | −1.4352 | 0.8747 | 0.3068 | 0.040* | |
C10 | −1.0668 (3) | 0.92464 (14) | 0.36235 (14) | 0.0294 (5) | |
H10A | −1.1766 | 0.9571 | 0.3394 | 0.035* | |
C15 | −1.5432 (3) | 0.65543 (17) | 0.27832 (15) | 0.0385 (6) | |
C12 | −1.2379 (3) | 0.77070 (14) | 0.33372 (13) | 0.0265 (5) | |
C4 | −0.5740 (3) | 1.38854 (15) | 0.43586 (16) | 0.0374 (6) | |
H4A | −0.4585 | 1.4226 | 0.4458 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0450 (9) | 0.0381 (8) | 0.0906 (12) | 0.0127 (6) | 0.0004 (8) | 0.0083 (8) |
F2 | 0.0554 (10) | 0.0552 (9) | 0.0619 (10) | −0.0309 (7) | −0.0138 (7) | −0.0001 (7) |
O3 | 0.0275 (8) | 0.0281 (8) | 0.0588 (11) | 0.0005 (6) | −0.0106 (7) | −0.0042 (7) |
O2 | 0.0258 (8) | 0.0298 (8) | 0.0483 (9) | −0.0013 (6) | −0.0062 (7) | 0.0013 (7) |
O1 | 0.0295 (9) | 0.0346 (8) | 0.0530 (10) | −0.0088 (7) | −0.0058 (7) | 0.0058 (7) |
C16 | 0.0306 (12) | 0.0444 (13) | 0.0363 (13) | −0.0028 (10) | 0.0002 (9) | −0.0039 (10) |
C6 | 0.0374 (13) | 0.0306 (11) | 0.0434 (13) | 0.0058 (10) | 0.0033 (10) | 0.0042 (10) |
C9 | 0.0268 (11) | 0.0301 (11) | 0.0258 (11) | 0.0005 (9) | −0.0012 (8) | 0.0017 (8) |
C1 | 0.0235 (10) | 0.0308 (11) | 0.0231 (10) | 0.0005 (8) | 0.0001 (8) | 0.0016 (8) |
C7 | 0.0307 (12) | 0.0318 (11) | 0.0358 (12) | −0.0020 (9) | 0.0008 (9) | 0.0010 (9) |
C5 | 0.0508 (15) | 0.0260 (11) | 0.0438 (14) | −0.0027 (10) | 0.0066 (11) | 0.0006 (10) |
C13 | 0.0369 (13) | 0.0324 (11) | 0.0313 (12) | −0.0010 (9) | 0.0002 (9) | 0.0019 (9) |
C8 | 0.0251 (11) | 0.0297 (11) | 0.0310 (11) | −0.0015 (8) | −0.0066 (8) | 0.0042 (9) |
C3 | 0.0307 (12) | 0.0315 (11) | 0.0269 (11) | −0.0046 (9) | 0.0012 (9) | 0.0016 (9) |
C14 | 0.0535 (15) | 0.0282 (11) | 0.0383 (13) | −0.0097 (11) | 0.0018 (11) | −0.0012 (10) |
C11 | 0.0271 (12) | 0.0333 (11) | 0.0257 (11) | 0.0009 (9) | 0.0005 (8) | −0.0027 (9) |
C2 | 0.0305 (11) | 0.0284 (11) | 0.0224 (10) | −0.0028 (9) | 0.0023 (8) | 0.0013 (8) |
C17 | 0.0296 (12) | 0.0331 (11) | 0.0367 (12) | −0.0009 (9) | 0.0014 (9) | −0.0043 (9) |
C10 | 0.0274 (11) | 0.0316 (11) | 0.0290 (11) | −0.0011 (9) | −0.0051 (9) | 0.0000 (9) |
C15 | 0.0398 (14) | 0.0441 (13) | 0.0317 (12) | −0.0205 (11) | −0.0008 (10) | −0.0013 (10) |
C12 | 0.0299 (11) | 0.0291 (10) | 0.0206 (10) | −0.0032 (9) | 0.0018 (8) | −0.0019 (8) |
C4 | 0.0413 (14) | 0.0312 (11) | 0.0397 (13) | −0.0108 (10) | 0.0026 (10) | −0.0030 (10) |
F1—C6 | 1.362 (2) | C5—C4 | 1.368 (3) |
F2—C15 | 1.358 (2) | C5—H5A | 0.9300 |
O3—C9 | 1.323 (2) | C13—C14 | 1.377 (3) |
O3—H3A | 0.8200 | C13—C12 | 1.392 (3) |
O2—C1 | 1.262 (2) | C13—H13A | 0.9300 |
O1—C3 | 1.345 (2) | C8—H8A | 0.9300 |
O1—H1A | 0.8200 | C3—C4 | 1.385 (3) |
C16—C15 | 1.363 (3) | C3—C2 | 1.404 (3) |
C16—C17 | 1.367 (3) | C14—C15 | 1.366 (3) |
C16—H16A | 0.9300 | C14—H14A | 0.9300 |
C6—C7 | 1.358 (3) | C11—C10 | 1.323 (3) |
C6—C5 | 1.369 (3) | C11—C12 | 1.454 (3) |
C9—C8 | 1.357 (3) | C11—H11A | 0.9300 |
C9—C10 | 1.439 (3) | C17—C12 | 1.391 (3) |
C1—C8 | 1.422 (3) | C17—H17A | 0.9300 |
C1—C2 | 1.472 (3) | C10—H10A | 0.9300 |
C7—C2 | 1.404 (3) | C4—H4A | 0.9300 |
C7—H7A | 0.9300 | ||
C9—O3—H3A | 109.5 | O1—C3—C2 | 123.41 (18) |
C3—O1—H1A | 109.5 | C4—C3—C2 | 119.84 (19) |
C15—C16—C17 | 118.1 (2) | C15—C14—C13 | 118.1 (2) |
C15—C16—H16A | 120.9 | C15—C14—H14A | 121.0 |
C17—C16—H16A | 120.9 | C13—C14—H14A | 121.0 |
C7—C6—F1 | 118.4 (2) | C10—C11—C12 | 126.55 (19) |
C7—C6—C5 | 122.9 (2) | C10—C11—H11A | 116.7 |
F1—C6—C5 | 118.66 (19) | C12—C11—H11A | 116.7 |
O3—C9—C8 | 122.42 (18) | C3—C2—C7 | 118.35 (18) |
O3—C9—C10 | 115.18 (17) | C3—C2—C1 | 120.26 (18) |
C8—C9—C10 | 122.40 (18) | C7—C2—C1 | 121.38 (18) |
O2—C1—C8 | 119.71 (18) | C16—C17—C12 | 121.6 (2) |
O2—C1—C2 | 118.55 (17) | C16—C17—H17A | 119.2 |
C8—C1—C2 | 121.72 (18) | C12—C17—H17A | 119.2 |
C6—C7—C2 | 119.3 (2) | C11—C10—C9 | 124.61 (19) |
C6—C7—H7A | 120.4 | C11—C10—H10A | 117.7 |
C2—C7—H7A | 120.4 | C9—C10—H10A | 117.7 |
C4—C5—C6 | 118.6 (2) | F2—C15—C16 | 118.1 (2) |
C4—C5—H5A | 120.7 | F2—C15—C14 | 118.8 (2) |
C6—C5—H5A | 120.7 | C16—C15—C14 | 123.1 (2) |
C14—C13—C12 | 121.1 (2) | C17—C12—C13 | 117.98 (19) |
C14—C13—H13A | 119.5 | C17—C12—C11 | 122.39 (18) |
C12—C13—H13A | 119.5 | C13—C12—C11 | 119.63 (19) |
C9—C8—C1 | 122.19 (19) | C5—C4—C3 | 121.0 (2) |
C9—C8—H8A | 118.9 | C5—C4—H4A | 119.5 |
C1—C8—H8A | 118.9 | C3—C4—H4A | 119.5 |
O1—C3—C4 | 116.75 (18) | ||
F1—C6—C7—C2 | −179.82 (18) | C8—C1—C2—C7 | 9.5 (3) |
C5—C6—C7—C2 | 0.0 (4) | C15—C16—C17—C12 | 0.0 (3) |
C7—C6—C5—C4 | −0.7 (4) | C12—C11—C10—C9 | 178.58 (19) |
F1—C6—C5—C4 | 179.0 (2) | O3—C9—C10—C11 | 1.7 (3) |
O3—C9—C8—C1 | 0.7 (3) | C8—C9—C10—C11 | −178.0 (2) |
C10—C9—C8—C1 | −179.63 (18) | C17—C16—C15—F2 | −179.84 (19) |
O2—C1—C8—C9 | 0.8 (3) | C17—C16—C15—C14 | 0.2 (4) |
C2—C1—C8—C9 | 179.13 (19) | C13—C14—C15—F2 | 179.86 (19) |
C12—C13—C14—C15 | −0.1 (3) | C13—C14—C15—C16 | −0.2 (4) |
O1—C3—C2—C7 | 178.50 (19) | C16—C17—C12—C13 | −0.3 (3) |
C4—C3—C2—C7 | −2.1 (3) | C16—C17—C12—C11 | 179.90 (19) |
O1—C3—C2—C1 | −2.1 (3) | C14—C13—C12—C17 | 0.3 (3) |
C4—C3—C2—C1 | 177.29 (19) | C14—C13—C12—C11 | −179.87 (19) |
C6—C7—C2—C3 | 1.4 (3) | C10—C11—C12—C17 | −4.8 (3) |
C6—C7—C2—C1 | −177.92 (19) | C10—C11—C12—C13 | 175.4 (2) |
O2—C1—C2—C3 | 8.5 (3) | C6—C5—C4—C3 | 0.1 (3) |
C8—C1—C2—C3 | −169.85 (18) | O1—C3—C4—C5 | −179.18 (19) |
O2—C1—C2—C7 | −172.14 (18) | C2—C3—C4—C5 | 1.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2 | 0.82 | 1.84 | 2.558 (2) | 145 |
O1—H1A···O3i | 0.82 | 2.55 | 3.145 (2) | 130 |
O3—H3A···O2 | 0.82 | 1.81 | 2.532 (2) | 146 |
O3—H3A···O2i | 0.82 | 2.38 | 2.856 (2) | 118 |
C10—H10A···F2ii | 0.93 | 2.51 | 3.326 (3) | 147 |
Symmetry codes: (i) −x−1, −y+2, −z+1; (ii) −x−3, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2 | 0.82 | 1.84 | 2.558 (2) | 145 |
O1—H1A···O3i | 0.82 | 2.55 | 3.145 (2) | 130 |
O3—H3A···O2 | 0.82 | 1.81 | 2.532 (2) | 146 |
O3—H3A···O2i | 0.82 | 2.38 | 2.856 (2) | 118 |
C10—H10A···F2ii | 0.93 | 2.51 | 3.326 (3) | 147 |
Symmetry codes: (i) −x−1, −y+2, −z+1; (ii) −x−3, y+1/2, −z+1/2. |
Acknowledgements
This work was supported financially by the National Science Foundation of China (grants No. 81072549 and 81302652) and the Natural Science Foundation of Fujian Province of China (grant No. 2011 J05101)
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Dibenzoylmethane (1,3-Diphenyl-propane-1,3-dione, DBM) and chalcones have been found to exhibit a variety of biological activities, such as anti-tumor, anti-inflammatory, antibacterial, anti-parasitic, anti-oxidation and anti-viral effect (Schobert et al., 2009; Meng et al., 2007). Recently, we carried out to synthesis a series of (E)-1,5-diphenylpent-4-ene-1,3-dione derivatives. These compounds have keto-enol tautomerism, however, the enol form predominates. The dihedral angle between the planes of the phenyl rings (C2–C7) and (C12–C17) is 8.6 (3) °. Bond lengths and angles in (I, Fig. 2) are agreement with values reported for a similar compound (Fun et al., 2012). In the crystal, two pairs of O—H···O hydrogen bonds connect the molecules into inversion dimers (Fig. 3). In addition, weak C—H···F hydrogen bonds link dimers into a two-dimensional network parallel to (104) (Fig. 4). The oxygen atom of the –C═O group is an acceptor for two intramolecular hydrogen bonds (Fig. 2).