organic compounds
(E)-1-Phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one
aResearch Center for Engineering Technology of Polymeric Composites of Shanxi Province, College of Materials Science and Engineering, North University of China, Taiyuan 030051, People's Republic of China, and bKey Laboratory of Green Chemical Media and Reactions, Ministry of Education, College of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453007, People's Republic of China
*Correspondence e-mail: zph2004@yahoo.com.cn
In the title compound, C16H11F3O, the dihedral angle between the two rings is 48.8 (2)°. The crystal packing exhibits no classical intermolecular interactions between the molecules.
Related literature
For applications of related compounds, see: Shibata (1994); Devincenzo et al. (1995); Dimmock et al. (1999); Go et al. (2005).
Experimental
Crystal data
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Data collection: CrystalClear (Rigaku/MSC, 2005); cell CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005).
Supporting information
10.1107/S1600536812035763/aa2055sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812035763/aa2055Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812035763/aa2055Isup3.cml
In 25 ml round-bottomed flask, the acetophenone (5.0 mmol) and sodium hydroxide (7.5 mmol) were dissolved in ethanol (2 ml), and the mixture was stirred at room temperature for 5 min followed by addition of 4-trifluoromethylbenzaldehyde (5.0 mmol). The reaction mixture was then stirred at room temperature and monitored by TLC until the reaction completed. The solid was filtered, washed with cold water, recrystallized from ethanol, and dried in vacuo to give the desired product. Crystals of the title compound were obtained by slow evaporation of the dichloromethane/n-hexane solution (1:1) at room temperature. 1N NMR(400 MHz, CDCl3, TMS): 7.53 (dd, 2H, J = 7.6, 15.6 Hz), 7.60 (m, 2H), 7.68 (d, 2H, J = 8.0 Hz), 7.75 (d, 2H, J = 8.0 Hz), 7.82 (d, 1H, J = 15.6 Hz), 8.03 (d, 2H, J = 8.4 Hz) p.p.m..
All the H atoms were positioned geometrically (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell
CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: CrystalStructure (Rigaku/MSC, 2005).Fig.1. The molecular structure of the title compound. Thermal displacement ellipsoids are drawn at the 30% probability level and H atoms are omitted. Fig 2. The crystal packing of the title compound. |
C16H11F3O | F(000) = 568 |
Mr = 276.25 | Dx = 1.463 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4102 reflections |
a = 14.7469 (5) Å | θ = 2.0–28.0° |
b = 14.5697 (4) Å | µ = 0.12 mm−1 |
c = 5.8430 (2) Å | T = 113 K |
β = 92.854 (1)° | Prism, colorless |
V = 1253.86 (7) Å3 | 0.20 × 0.18 × 0.08 mm |
Z = 4 |
Rigaku Saturn724 CCD diffractometer | 3005 independent reflections |
Radiation source: rotating anode | 2037 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.049 |
Detector resolution: 14.22 pixels mm-1 | θmax = 27.9°, θmin = 2.0° |
ω and ϕ scans | h = −19→19 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −14→19 |
Tmin = 0.976, Tmax = 0.990 | l = −7→7 |
12984 measured reflections |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0283P)2] where P = (Fo2 + 2Fc2)/3 |
3005 reflections | (Δ/σ)max = 0.001 |
181 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C16H11F3O | V = 1253.86 (7) Å3 |
Mr = 276.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.7469 (5) Å | µ = 0.12 mm−1 |
b = 14.5697 (4) Å | T = 113 K |
c = 5.8430 (2) Å | 0.20 × 0.18 × 0.08 mm |
β = 92.854 (1)° |
Rigaku Saturn724 CCD diffractometer | 3005 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | 2037 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.990 | Rint = 0.049 |
12984 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.22 e Å−3 |
3005 reflections | Δρmin = −0.27 e Å−3 |
181 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 | 1.01951 (5) | 0.12265 (5) | 1.04772 (13) | 0.0377 (2) | |
F2 | 0.95432 (5) | 0.05980 (5) | 1.32422 (13) | 0.0375 (2) | |
F3 | 0.95565 (5) | 0.20580 (5) | 1.29461 (15) | 0.0493 (3) | |
O1 | 0.47484 (6) | 0.13892 (6) | 0.27878 (15) | 0.0329 (2) | |
C1 | 0.29314 (8) | 0.16320 (7) | 0.3888 (2) | 0.0215 (3) | |
H1 | 0.3095 | 0.1866 | 0.2449 | 0.026* | |
C2 | 0.20299 (9) | 0.16081 (7) | 0.4417 (2) | 0.0243 (3) | |
H2 | 0.1576 | 0.1834 | 0.3353 | 0.029* | |
C3 | 0.17888 (9) | 0.12555 (8) | 0.6496 (2) | 0.0249 (3) | |
H3 | 0.1168 | 0.1235 | 0.6851 | 0.030* | |
C4 | 0.24500 (8) | 0.09312 (8) | 0.8068 (2) | 0.0251 (3) | |
H4 | 0.2280 | 0.0684 | 0.9489 | 0.030* | |
C5 | 0.33571 (8) | 0.09691 (8) | 0.7565 (2) | 0.0225 (3) | |
H5 | 0.3811 | 0.0761 | 0.8655 | 0.027* | |
C6 | 0.36044 (8) | 0.13127 (7) | 0.5461 (2) | 0.0198 (3) | |
C7 | 0.45675 (8) | 0.13432 (8) | 0.4807 (2) | 0.0220 (3) | |
C8 | 0.52985 (8) | 0.13323 (8) | 0.6661 (2) | 0.0230 (3) | |
H8 | 0.5162 | 0.1474 | 0.8193 | 0.028* | |
C9 | 0.61401 (8) | 0.11232 (7) | 0.6158 (2) | 0.0207 (3) | |
H9 | 0.6223 | 0.0939 | 0.4623 | 0.025* | |
C10 | 0.69610 (8) | 0.11424 (7) | 0.7696 (2) | 0.0188 (3) | |
C11 | 0.77584 (8) | 0.07768 (7) | 0.6888 (2) | 0.0202 (3) | |
H11 | 0.7745 | 0.0490 | 0.5426 | 0.024* | |
C12 | 0.85708 (8) | 0.08253 (8) | 0.8182 (2) | 0.0211 (3) | |
H12 | 0.9109 | 0.0571 | 0.7615 | 0.025* | |
C13 | 0.85929 (8) | 0.12479 (7) | 1.0312 (2) | 0.0185 (3) | |
C14 | 0.78038 (8) | 0.16112 (7) | 1.1158 (2) | 0.0202 (3) | |
H14 | 0.7820 | 0.1899 | 1.2619 | 0.024* | |
C15 | 0.69934 (8) | 0.15519 (7) | 0.9860 (2) | 0.0205 (3) | |
H15 | 0.6453 | 0.1793 | 1.0449 | 0.025* | |
C16 | 0.94629 (8) | 0.12902 (8) | 1.1725 (2) | 0.0234 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0177 (4) | 0.0663 (5) | 0.0293 (5) | −0.0017 (4) | 0.0027 (3) | 0.0043 (4) |
F2 | 0.0314 (5) | 0.0496 (5) | 0.0311 (5) | 0.0037 (3) | −0.0037 (4) | 0.0171 (4) |
F3 | 0.0378 (5) | 0.0427 (5) | 0.0648 (6) | 0.0105 (4) | −0.0231 (5) | −0.0281 (4) |
O1 | 0.0250 (5) | 0.0531 (6) | 0.0208 (5) | −0.0003 (4) | 0.0020 (4) | 0.0019 (4) |
C1 | 0.0247 (7) | 0.0216 (6) | 0.0180 (7) | −0.0040 (5) | −0.0002 (5) | 0.0000 (5) |
C2 | 0.0216 (7) | 0.0227 (7) | 0.0282 (8) | −0.0008 (5) | −0.0028 (6) | −0.0013 (5) |
C3 | 0.0217 (7) | 0.0240 (7) | 0.0291 (7) | −0.0045 (5) | 0.0044 (6) | −0.0065 (6) |
C4 | 0.0313 (7) | 0.0248 (7) | 0.0198 (7) | −0.0074 (6) | 0.0059 (6) | −0.0031 (5) |
C5 | 0.0254 (7) | 0.0224 (6) | 0.0193 (7) | −0.0015 (5) | −0.0023 (5) | 0.0004 (5) |
C6 | 0.0206 (6) | 0.0190 (6) | 0.0198 (7) | −0.0023 (5) | 0.0000 (5) | −0.0023 (5) |
C7 | 0.0222 (7) | 0.0229 (6) | 0.0209 (7) | 0.0002 (5) | 0.0010 (5) | 0.0009 (5) |
C8 | 0.0234 (7) | 0.0259 (7) | 0.0197 (7) | −0.0017 (5) | 0.0008 (5) | −0.0011 (5) |
C9 | 0.0239 (7) | 0.0195 (6) | 0.0188 (7) | −0.0013 (5) | 0.0008 (5) | −0.0010 (5) |
C10 | 0.0206 (6) | 0.0157 (6) | 0.0201 (7) | −0.0012 (5) | 0.0013 (5) | 0.0026 (5) |
C11 | 0.0248 (7) | 0.0194 (6) | 0.0165 (6) | 0.0011 (5) | 0.0025 (5) | −0.0007 (5) |
C12 | 0.0201 (6) | 0.0223 (6) | 0.0211 (7) | 0.0033 (5) | 0.0042 (5) | 0.0007 (5) |
C13 | 0.0197 (6) | 0.0174 (6) | 0.0183 (6) | 0.0006 (5) | 0.0003 (5) | 0.0029 (5) |
C14 | 0.0238 (7) | 0.0199 (6) | 0.0170 (6) | 0.0020 (5) | 0.0020 (5) | −0.0013 (5) |
C15 | 0.0199 (7) | 0.0208 (6) | 0.0211 (7) | 0.0031 (5) | 0.0048 (5) | 0.0005 (5) |
C16 | 0.0224 (7) | 0.0255 (7) | 0.0226 (7) | 0.0032 (5) | 0.0027 (5) | −0.0010 (6) |
F1—C16 | 1.3361 (14) | C7—C8 | 1.4896 (16) |
F2—C16 | 1.3439 (14) | C8—C9 | 1.3249 (16) |
F3—C16 | 1.3301 (14) | C8—H8 | 0.9500 |
O1—C7 | 1.2244 (14) | C9—C10 | 1.4715 (16) |
C1—C2 | 1.3802 (17) | C9—H9 | 0.9500 |
C1—C6 | 1.3981 (16) | C10—C11 | 1.3946 (16) |
C1—H1 | 0.9500 | C10—C15 | 1.3967 (16) |
C2—C3 | 1.3815 (17) | C11—C12 | 1.3866 (16) |
C2—H2 | 0.9500 | C11—H11 | 0.9500 |
C3—C4 | 1.3889 (17) | C12—C13 | 1.3874 (16) |
C3—H3 | 0.9500 | C12—H12 | 0.9500 |
C4—C5 | 1.3850 (16) | C13—C14 | 1.3914 (15) |
C4—H4 | 0.9500 | C13—C16 | 1.4920 (16) |
C5—C6 | 1.3929 (16) | C14—C15 | 1.3860 (16) |
C5—H5 | 0.9500 | C14—H14 | 0.9500 |
C6—C7 | 1.4897 (16) | C15—H15 | 0.9500 |
C2—C1—C6 | 120.29 (12) | C10—C9—H9 | 116.1 |
C2—C1—H1 | 119.9 | C11—C10—C15 | 118.58 (11) |
C6—C1—H1 | 119.9 | C11—C10—C9 | 117.90 (11) |
C1—C2—C3 | 119.95 (12) | C15—C10—C9 | 123.42 (11) |
C1—C2—H2 | 120.0 | C12—C11—C10 | 121.06 (11) |
C3—C2—H2 | 120.0 | C12—C11—H11 | 119.5 |
C2—C3—C4 | 120.34 (12) | C10—C11—H11 | 119.5 |
C2—C3—H3 | 119.8 | C11—C12—C13 | 119.55 (11) |
C4—C3—H3 | 119.8 | C11—C12—H12 | 120.2 |
C5—C4—C3 | 119.98 (12) | C13—C12—H12 | 120.2 |
C5—C4—H4 | 120.0 | C12—C13—C14 | 120.32 (11) |
C3—C4—H4 | 120.0 | C12—C13—C16 | 119.73 (11) |
C4—C5—C6 | 119.99 (11) | C14—C13—C16 | 119.94 (11) |
C4—C5—H5 | 120.0 | C15—C14—C13 | 119.70 (11) |
C6—C5—H5 | 120.0 | C15—C14—H14 | 120.1 |
C5—C6—C1 | 119.43 (11) | C13—C14—H14 | 120.1 |
C5—C6—C7 | 122.13 (11) | C14—C15—C10 | 120.78 (11) |
C1—C6—C7 | 118.44 (11) | C14—C15—H15 | 119.6 |
O1—C7—C8 | 121.12 (11) | C10—C15—H15 | 119.6 |
O1—C7—C6 | 120.32 (11) | F3—C16—F1 | 106.62 (10) |
C8—C7—C6 | 118.56 (11) | F3—C16—F2 | 105.91 (10) |
C9—C8—C7 | 119.56 (11) | F1—C16—F2 | 105.12 (9) |
C9—C8—H8 | 120.2 | F3—C16—C13 | 113.26 (10) |
C7—C8—H8 | 120.2 | F1—C16—C13 | 113.02 (10) |
C8—C9—C10 | 127.71 (12) | F2—C16—C13 | 112.27 (10) |
C8—C9—H9 | 116.1 | ||
C6—C1—C2—C3 | −0.92 (17) | C15—C10—C11—C12 | −0.73 (17) |
C1—C2—C3—C4 | 0.55 (17) | C9—C10—C11—C12 | 175.76 (10) |
C2—C3—C4—C5 | 0.65 (17) | C10—C11—C12—C13 | −0.31 (17) |
C3—C4—C5—C6 | −1.48 (17) | C11—C12—C13—C14 | 0.78 (17) |
C4—C5—C6—C1 | 1.10 (17) | C11—C12—C13—C16 | 179.16 (10) |
C4—C5—C6—C7 | −178.18 (10) | C12—C13—C14—C15 | −0.18 (17) |
C2—C1—C6—C5 | 0.10 (17) | C16—C13—C14—C15 | −178.57 (10) |
C2—C1—C6—C7 | 179.41 (10) | C13—C14—C15—C10 | −0.88 (16) |
C5—C6—C7—O1 | 158.69 (12) | C11—C10—C15—C14 | 1.33 (16) |
C1—C6—C7—O1 | −20.61 (16) | C9—C10—C15—C14 | −174.95 (10) |
C5—C6—C7—C8 | −22.32 (16) | C12—C13—C16—F3 | 145.25 (11) |
C1—C6—C7—C8 | 158.38 (10) | C14—C13—C16—F3 | −36.36 (16) |
O1—C7—C8—C9 | −18.27 (17) | C12—C13—C16—F1 | 23.86 (15) |
C6—C7—C8—C9 | 162.75 (11) | C14—C13—C16—F1 | −157.75 (10) |
C7—C8—C9—C10 | 175.00 (10) | C12—C13—C16—F2 | −94.84 (13) |
C8—C9—C10—C11 | 171.53 (11) | C14—C13—C16—F2 | 83.55 (13) |
C8—C9—C10—C15 | −12.17 (19) |
Experimental details
Crystal data | |
Chemical formula | C16H11F3O |
Mr | 276.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 113 |
a, b, c (Å) | 14.7469 (5), 14.5697 (4), 5.8430 (2) |
β (°) | 92.854 (1) |
V (Å3) | 1253.86 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.20 × 0.18 × 0.08 |
Data collection | |
Diffractometer | Rigaku Saturn724 CCD diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2005) |
Tmin, Tmax | 0.976, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12984, 3005, 2037 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.659 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.078, 1.12 |
No. of reflections | 3005 |
No. of parameters | 181 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.27 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).
Acknowledgements
This work was supported financially by the National Natural Science Foundation of China (No. 51102216) and Shanxi Province Science Foundation for Youths (No. 2012021007-4).
References
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Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125–1149. Web of Science PubMed CAS Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound belongs to the chalcones, which are Michael acceptors and constitute an important group of natural products that belong to the flavonoid family (Dimmock et al., 1999; Go et al., 2005). Natural and synthetic chalcones have been reported to possess strong antiproliferative effects in ovarian cancer cells and in gastic cancer cells (Shibata, 1994; Devincenzo et al., 1995).
The dihedral angle between two benzene rings is 48.8 (2) ° (Fig. 1). The crystal packing shows no π···π or other classical intermolecular interactions (Fig. 2).