organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(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

(Received 13 March 2012; accepted 14 August 2012; online 23 August 2012)

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[Shibata, S. (1994). Stem Cells, 12, 44-52.]); Devincenzo et al. (1995[Devincenzo, R., Scambia, G., Panici, P. B., Ranelletti, F. O., Bonanno, G., Ercoli, A., Dellemonache, F., Ferrari, F., Piantelli, M. & Mancuso, S. (1995). Drug Des. 10, 481-490.]); Dimmock et al. (1999[Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.]); Go et al. (2005[Go, M. L., Wu, X. & Liu, X. L. (2005). Curr. Med. Chem. 12, 483-499.]).

[Scheme 1]

Experimental

Crystal data
  • C16H11F3O

  • Mr = 276.25

  • Monoclinic, P 21 /c

  • a = 14.7469 (5) Å

  • b = 14.5697 (4) Å

  • c = 5.8430 (2) Å

  • β = 92.854 (1)°

  • V = 1253.86 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 113 K

  • 0.20 × 0.18 × 0.08 mm

Data collection
  • Rigaku Saturn724 CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA.]) Tmin = 0.976, Tmax = 0.990

  • 12984 measured reflections

  • 3005 independent reflections

  • 2037 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.078

  • S = 1.12

  • 3005 reflections

  • 181 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA.]).

Supporting information


Comment top

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).

Related literature top

For applications of related compounds, see: Shibata (1994); Devincenzo et al. (1995); Dimmock et al. (1999); Go et al. (2005).

Experimental top

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..

Refinement top

All the H atoms were positioned geometrically (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: 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).

Figures top
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.
(E)-1-Phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one top
Crystal data top
C16H11F3OF(000) = 568
Mr = 276.25Dx = 1.463 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4102 reflections
a = 14.7469 (5) Åθ = 2.0–28.0°
b = 14.5697 (4) ŵ = 0.12 mm1
c = 5.8430 (2) ÅT = 113 K
β = 92.854 (1)°Prism, colorless
V = 1253.86 (7) Å30.20 × 0.18 × 0.08 mm
Z = 4
Data collection top
Rigaku Saturn724 CCD
diffractometer
3005 independent reflections
Radiation source: rotating anode2037 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.049
Detector resolution: 14.22 pixels mm-1θmax = 27.9°, θmin = 2.0°
ω and ϕ scansh = 1919
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 1419
Tmin = 0.976, Tmax = 0.990l = 77
12984 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-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 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C16H11F3OV = 1253.86 (7) Å3
Mr = 276.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.7469 (5) ŵ = 0.12 mm1
b = 14.5697 (4) ÅT = 113 K
c = 5.8430 (2) Å0.20 × 0.18 × 0.08 mm
β = 92.854 (1)°
Data collection top
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 = 0.990Rint = 0.049
12984 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.078H-atom parameters constrained
S = 1.12Δρmax = 0.22 e Å3
3005 reflectionsΔρmin = 0.27 e Å3
181 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F11.01951 (5)0.12265 (5)1.04772 (13)0.0377 (2)
F20.95432 (5)0.05980 (5)1.32422 (13)0.0375 (2)
F30.95565 (5)0.20580 (5)1.29461 (15)0.0493 (3)
O10.47484 (6)0.13892 (6)0.27878 (15)0.0329 (2)
C10.29314 (8)0.16320 (7)0.3888 (2)0.0215 (3)
H10.30950.18660.24490.026*
C20.20299 (9)0.16081 (7)0.4417 (2)0.0243 (3)
H20.15760.18340.33530.029*
C30.17888 (9)0.12555 (8)0.6496 (2)0.0249 (3)
H30.11680.12350.68510.030*
C40.24500 (8)0.09312 (8)0.8068 (2)0.0251 (3)
H40.22800.06840.94890.030*
C50.33571 (8)0.09691 (8)0.7565 (2)0.0225 (3)
H50.38110.07610.86550.027*
C60.36044 (8)0.13127 (7)0.5461 (2)0.0198 (3)
C70.45675 (8)0.13432 (8)0.4807 (2)0.0220 (3)
C80.52985 (8)0.13323 (8)0.6661 (2)0.0230 (3)
H80.51620.14740.81930.028*
C90.61401 (8)0.11232 (7)0.6158 (2)0.0207 (3)
H90.62230.09390.46230.025*
C100.69610 (8)0.11424 (7)0.7696 (2)0.0188 (3)
C110.77584 (8)0.07768 (7)0.6888 (2)0.0202 (3)
H110.77450.04900.54260.024*
C120.85708 (8)0.08253 (8)0.8182 (2)0.0211 (3)
H120.91090.05710.76150.025*
C130.85929 (8)0.12479 (7)1.0312 (2)0.0185 (3)
C140.78038 (8)0.16112 (7)1.1158 (2)0.0202 (3)
H140.78200.18991.26190.024*
C150.69934 (8)0.15519 (7)0.9860 (2)0.0205 (3)
H150.64530.17931.04490.025*
C160.94629 (8)0.12902 (8)1.1725 (2)0.0234 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0177 (4)0.0663 (5)0.0293 (5)0.0017 (4)0.0027 (3)0.0043 (4)
F20.0314 (5)0.0496 (5)0.0311 (5)0.0037 (3)0.0037 (4)0.0171 (4)
F30.0378 (5)0.0427 (5)0.0648 (6)0.0105 (4)0.0231 (5)0.0281 (4)
O10.0250 (5)0.0531 (6)0.0208 (5)0.0003 (4)0.0020 (4)0.0019 (4)
C10.0247 (7)0.0216 (6)0.0180 (7)0.0040 (5)0.0002 (5)0.0000 (5)
C20.0216 (7)0.0227 (7)0.0282 (8)0.0008 (5)0.0028 (6)0.0013 (5)
C30.0217 (7)0.0240 (7)0.0291 (7)0.0045 (5)0.0044 (6)0.0065 (6)
C40.0313 (7)0.0248 (7)0.0198 (7)0.0074 (6)0.0059 (6)0.0031 (5)
C50.0254 (7)0.0224 (6)0.0193 (7)0.0015 (5)0.0023 (5)0.0004 (5)
C60.0206 (6)0.0190 (6)0.0198 (7)0.0023 (5)0.0000 (5)0.0023 (5)
C70.0222 (7)0.0229 (6)0.0209 (7)0.0002 (5)0.0010 (5)0.0009 (5)
C80.0234 (7)0.0259 (7)0.0197 (7)0.0017 (5)0.0008 (5)0.0011 (5)
C90.0239 (7)0.0195 (6)0.0188 (7)0.0013 (5)0.0008 (5)0.0010 (5)
C100.0206 (6)0.0157 (6)0.0201 (7)0.0012 (5)0.0013 (5)0.0026 (5)
C110.0248 (7)0.0194 (6)0.0165 (6)0.0011 (5)0.0025 (5)0.0007 (5)
C120.0201 (6)0.0223 (6)0.0211 (7)0.0033 (5)0.0042 (5)0.0007 (5)
C130.0197 (6)0.0174 (6)0.0183 (6)0.0006 (5)0.0003 (5)0.0029 (5)
C140.0238 (7)0.0199 (6)0.0170 (6)0.0020 (5)0.0020 (5)0.0013 (5)
C150.0199 (7)0.0208 (6)0.0211 (7)0.0031 (5)0.0048 (5)0.0005 (5)
C160.0224 (7)0.0255 (7)0.0226 (7)0.0032 (5)0.0027 (5)0.0010 (6)
Geometric parameters (Å, º) top
F1—C161.3361 (14)C7—C81.4896 (16)
F2—C161.3439 (14)C8—C91.3249 (16)
F3—C161.3301 (14)C8—H80.9500
O1—C71.2244 (14)C9—C101.4715 (16)
C1—C21.3802 (17)C9—H90.9500
C1—C61.3981 (16)C10—C111.3946 (16)
C1—H10.9500C10—C151.3967 (16)
C2—C31.3815 (17)C11—C121.3866 (16)
C2—H20.9500C11—H110.9500
C3—C41.3889 (17)C12—C131.3874 (16)
C3—H30.9500C12—H120.9500
C4—C51.3850 (16)C13—C141.3914 (15)
C4—H40.9500C13—C161.4920 (16)
C5—C61.3929 (16)C14—C151.3860 (16)
C5—H50.9500C14—H140.9500
C6—C71.4897 (16)C15—H150.9500
C2—C1—C6120.29 (12)C10—C9—H9116.1
C2—C1—H1119.9C11—C10—C15118.58 (11)
C6—C1—H1119.9C11—C10—C9117.90 (11)
C1—C2—C3119.95 (12)C15—C10—C9123.42 (11)
C1—C2—H2120.0C12—C11—C10121.06 (11)
C3—C2—H2120.0C12—C11—H11119.5
C2—C3—C4120.34 (12)C10—C11—H11119.5
C2—C3—H3119.8C11—C12—C13119.55 (11)
C4—C3—H3119.8C11—C12—H12120.2
C5—C4—C3119.98 (12)C13—C12—H12120.2
C5—C4—H4120.0C12—C13—C14120.32 (11)
C3—C4—H4120.0C12—C13—C16119.73 (11)
C4—C5—C6119.99 (11)C14—C13—C16119.94 (11)
C4—C5—H5120.0C15—C14—C13119.70 (11)
C6—C5—H5120.0C15—C14—H14120.1
C5—C6—C1119.43 (11)C13—C14—H14120.1
C5—C6—C7122.13 (11)C14—C15—C10120.78 (11)
C1—C6—C7118.44 (11)C14—C15—H15119.6
O1—C7—C8121.12 (11)C10—C15—H15119.6
O1—C7—C6120.32 (11)F3—C16—F1106.62 (10)
C8—C7—C6118.56 (11)F3—C16—F2105.91 (10)
C9—C8—C7119.56 (11)F1—C16—F2105.12 (9)
C9—C8—H8120.2F3—C16—C13113.26 (10)
C7—C8—H8120.2F1—C16—C13113.02 (10)
C8—C9—C10127.71 (12)F2—C16—C13112.27 (10)
C8—C9—H9116.1
C6—C1—C2—C30.92 (17)C15—C10—C11—C120.73 (17)
C1—C2—C3—C40.55 (17)C9—C10—C11—C12175.76 (10)
C2—C3—C4—C50.65 (17)C10—C11—C12—C130.31 (17)
C3—C4—C5—C61.48 (17)C11—C12—C13—C140.78 (17)
C4—C5—C6—C11.10 (17)C11—C12—C13—C16179.16 (10)
C4—C5—C6—C7178.18 (10)C12—C13—C14—C150.18 (17)
C2—C1—C6—C50.10 (17)C16—C13—C14—C15178.57 (10)
C2—C1—C6—C7179.41 (10)C13—C14—C15—C100.88 (16)
C5—C6—C7—O1158.69 (12)C11—C10—C15—C141.33 (16)
C1—C6—C7—O120.61 (16)C9—C10—C15—C14174.95 (10)
C5—C6—C7—C822.32 (16)C12—C13—C16—F3145.25 (11)
C1—C6—C7—C8158.38 (10)C14—C13—C16—F336.36 (16)
O1—C7—C8—C918.27 (17)C12—C13—C16—F123.86 (15)
C6—C7—C8—C9162.75 (11)C14—C13—C16—F1157.75 (10)
C7—C8—C9—C10175.00 (10)C12—C13—C16—F294.84 (13)
C8—C9—C10—C11171.53 (11)C14—C13—C16—F283.55 (13)
C8—C9—C10—C1512.17 (19)

Experimental details

Crystal data
Chemical formulaC16H11F3O
Mr276.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)14.7469 (5), 14.5697 (4), 5.8430 (2)
β (°) 92.854 (1)
V3)1253.86 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.20 × 0.18 × 0.08
Data collection
DiffractometerRigaku Saturn724 CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.976, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
12984, 3005, 2037
Rint0.049
(sin θ/λ)max1)0.659
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.078, 1.12
No. of reflections3005
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

First citationDevincenzo, R., Scambia, G., Panici, P. B., Ranelletti, F. O., Bonanno, G., Ercoli, A., Dellemonache, F., Ferrari, F., Piantelli, M. & Mancuso, S. (1995). Drug Des. 10, 481–490.  CAS
First citationDimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125–1149.  Web of Science PubMed CAS
First citationGo, M. L., Wu, X. & Liu, X. L. (2005). Curr. Med. Chem. 12, 483–499.  CrossRef CAS
First citationRigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShibata, S. (1994). Stem Cells, 12, 44–52.  CrossRef CAS PubMed

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds