(E)-1-Phenyl-3-[4-(trifluoro-meth-yl)phen-yl]prop-2-en-1-one.

In the title compound, C(16)H(11)F(3)O, the dihedral angle between the two rings is 48.8 (2)°. The crystal packing exhibits no classical inter-molecular inter-actions between the mol-ecules.

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 = 276.25

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 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 ▶); 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035763/aa2055sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812035763/aa2055Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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)