(E)-1-Phenyl-3-[4-(trifluoro­meth­yl)phen­yl]prop-2-en-1-one

Zhao, P.-H.; Hao, E.-J.; Liu, Y.-Q.; Zhao, G.-Z.

doi:10.1107/S1600536812035763

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2750

doi:10.1107/S1600536812035763

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(E)-1-Phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one

Pei-Hua Zhao,^a ^* Er-Jun Hao,^b Ya-Qing Liu ^a and Gui-Zhe Zhao ^a

^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 ); Devincenzo et al. (1995 ); Dimmock et al. (1999 ); Go et al. (2005 ).

Experimental

Crystal data

C₁₆H₁₁F₃O
M_r = 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 ) T_min = 0.976, T_max = 0.990
12984 measured reflections
3005 independent reflections
2037 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.078
S = 1.12
3005 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812035763/aa2055sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812035763/aa2055Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812035763/aa2055Isup3.cml

checkCIF report

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..

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

C₁₆H₁₁F₃O	F(000) = 568
M_r = 276.25	D_x = 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

Data collection top

Rigaku Saturn724 CCD diffractometer	3005 independent reflections
Radiation source: rotating anode	2037 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.049
Detector resolution: 14.22 pixels mm^-1	θ_max = 27.9°, θ_min = 2.0°
ω and ϕ scans	h = −19→19
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −14→19
T_min = 0.976, T_max = 0.990	l = −7→7
12984 measured reflections

Refinement top

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(F_o²) + (0.0283P)²] where P = (F_o² + 2F_c²)/3
3005 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₆H₁₁F₃O	V = 1253.86 (7) Å³
M_r = 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)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3005 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2037 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.990	R_int = 0.049
12984 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.12	Δρ_max = 0.22 e Å⁻³
3005 reflections	Δρ_min = −0.27 e Å⁻³
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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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
M_r	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)
T_min, T_max	0.976, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	12984, 3005, 2037
R_int	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
Δρ_max, Δρ_min (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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