2-[2-(Trifluoro-meth-yl)phen-yl]-2H-1-benzopyran-4(3H)-one.

In the title compound, C(16)H(11)F(3)O(2), the γ-pyran-one ring adopts an envelope conformation with the chiral C atom standing out of the ring plane. In the crystal, molecules are linked by C-H⋯O and C-H⋯F inter-actions.

Related literature

For general background to flavones, see: Harborne & Williams (2000 ▶). For related flavonoids, see: Benavente-García & Castillo (2008 ▶); Rodeiro et al. (2006 ▶). For related structures, see: Wera et al. (2012 ▶); Białońska et al. (2007 ▶); Krishnaiah et al. (2005 ▶); Wu et al. (2005 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C16H11F3O2

M = 292.25

Orthorhombic,

a = 8.2291 (9) Å

b = 22.020 (3) Å

c = 7.3355 (11) Å

V = 1329.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.18 × 0.02 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer

4585 measured reflections

2558 independent reflections

1462 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.087

wR(F 2) = 0.109

S = 1.12

2558 reflections

190 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681201687X/kj2198sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201687X/kj2198Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201687X/kj2198Isup3.mol

Supplementary material file. DOI: 10.1107/S160053681201687X/kj2198Isup4.cml

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

C16H11F3O2	F(000) = 600
Mr = 292.25	Dx = 1.460 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 966 reflections
a = 8.2291 (9) Å	θ = 3.3–28.9°
b = 22.020 (3) Å	µ = 0.12 mm−1
c = 7.3355 (11) Å	T = 293 K
V = 1329.2 (3) Å3	Needle, colourless
Z = 4	0.18 × 0.02 × 0.02 mm

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	1462 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.049
Graphite monochromator	θmax = 28.9°, θmin = 3.7°
Detector resolution: 16.3280 pixels mm-1	h = −11→10
ω scans	k = −28→29
4585 measured reflections	l = −9→9
2558 independent 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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.025P)2] where P = (Fo2 + 2Fc2)/3
2558 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.15 e Å−3

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
O1	0.3661 (3)	0.90660 (11)	0.7245 (5)	0.0481 (8)
O2	−0.0253 (3)	1.02162 (14)	0.7338 (6)	0.0901 (14)
F1	0.0147 (4)	0.74844 (13)	0.3065 (5)	0.1002 (11)
F2	0.1886 (3)	0.82036 (13)	0.2974 (4)	0.0759 (8)
F3	−0.0440 (3)	0.83559 (15)	0.4155 (5)	0.0867 (10)
C1	0.3889 (4)	0.96841 (17)	0.7160 (7)	0.0394 (10)
C2	0.5488 (4)	0.98855 (19)	0.7098 (7)	0.0475 (12)
H2	0.6339	0.9608	0.7105	0.057*
C3	0.5801 (5)	1.04910 (19)	0.7029 (7)	0.0496 (12)
H3	0.6872	1.0626	0.7023	0.060*
C4	0.4543 (5)	1.09121 (19)	0.6967 (7)	0.0581 (13)
H4	0.4767	1.1325	0.6878	0.070*
C5	0.2973 (5)	1.07110 (18)	0.7040 (7)	0.0557 (13)
H5	0.2132	1.0993	0.7028	0.067*
C6	0.2595 (4)	1.00912 (18)	0.7131 (7)	0.0416 (11)
C7	0.0917 (5)	0.98787 (19)	0.7367 (8)	0.0563 (14)
C8	0.0756 (4)	0.92045 (17)	0.7675 (7)	0.0555 (15)
H8A	−0.0302	0.9070	0.7254	0.067*
H8B	0.0831	0.9119	0.8969	0.067*
C9	0.2082 (4)	0.88567 (18)	0.6662 (6)	0.0393 (11)
H9	0.1964	0.8925	0.5349	0.047*
C10	0.2017 (4)	0.81852 (19)	0.7043 (6)	0.0365 (10)
C11	0.1381 (5)	0.7759 (2)	0.5836 (6)	0.0387 (11)
C12	0.1326 (5)	0.7148 (2)	0.6313 (7)	0.0478 (13)
H12	0.0877	0.6868	0.5509	0.057*
C13	0.1925 (5)	0.6955 (2)	0.7952 (8)	0.0540 (12)
H13	0.1884	0.6545	0.8253	0.065*
C14	0.2581 (5)	0.7360 (2)	0.9145 (7)	0.0583 (14)
H14	0.2998	0.7227	1.0254	0.070*
C15	0.2626 (5)	0.7976 (2)	0.8697 (7)	0.0505 (13)
H15	0.3071	0.8252	0.9518	0.061*
C16	0.0756 (6)	0.7942 (2)	0.4026 (8)	0.0594 (15)

	U11	U22	U33	U12	U13	U23
O1	0.0319 (14)	0.0360 (17)	0.076 (2)	−0.0008 (13)	−0.0020 (16)	0.001 (2)
O2	0.0468 (16)	0.064 (2)	0.160 (4)	0.0188 (17)	0.013 (2)	0.002 (3)
F1	0.149 (3)	0.079 (2)	0.072 (2)	−0.041 (2)	−0.051 (2)	−0.002 (2)
F2	0.0938 (18)	0.087 (2)	0.0464 (17)	−0.0169 (17)	0.0070 (17)	0.0086 (19)
F3	0.0697 (18)	0.097 (2)	0.093 (2)	0.0126 (19)	−0.0212 (18)	0.022 (2)
C1	0.044 (2)	0.032 (2)	0.042 (3)	−0.002 (2)	0.007 (2)	−0.009 (3)
C2	0.035 (2)	0.046 (3)	0.062 (3)	0.000 (2)	0.007 (3)	0.001 (3)
C3	0.050 (2)	0.045 (3)	0.055 (3)	−0.011 (2)	0.006 (3)	0.005 (3)
C4	0.070 (3)	0.031 (2)	0.073 (4)	−0.011 (3)	0.018 (3)	−0.005 (3)
C5	0.060 (3)	0.036 (3)	0.071 (3)	0.009 (2)	0.010 (3)	−0.001 (3)
C6	0.041 (2)	0.036 (3)	0.049 (3)	0.002 (2)	0.005 (3)	−0.002 (3)
C7	0.047 (2)	0.047 (3)	0.076 (4)	0.002 (2)	0.006 (3)	−0.013 (4)
C8	0.037 (2)	0.045 (3)	0.085 (4)	−0.002 (2)	0.009 (3)	−0.004 (3)
C9	0.040 (2)	0.042 (2)	0.036 (3)	−0.003 (2)	0.005 (2)	−0.007 (2)
C10	0.0344 (19)	0.037 (3)	0.038 (3)	−0.005 (2)	0.001 (2)	0.002 (3)
C11	0.030 (2)	0.044 (3)	0.042 (3)	−0.001 (2)	−0.002 (2)	0.002 (3)
C12	0.056 (3)	0.041 (3)	0.046 (3)	−0.001 (3)	0.004 (2)	−0.005 (3)
C13	0.060 (3)	0.035 (3)	0.067 (3)	−0.004 (3)	0.005 (3)	0.006 (3)
C14	0.066 (3)	0.060 (4)	0.050 (3)	−0.009 (3)	−0.014 (3)	0.015 (3)
C15	0.061 (3)	0.046 (3)	0.045 (3)	−0.008 (2)	−0.001 (3)	−0.006 (3)
C16	0.060 (3)	0.058 (4)	0.060 (4)	−0.011 (3)	−0.016 (3)	0.001 (4)

O1—C1	1.376 (4)	C7—C8	1.508 (5)
O1—C9	1.443 (4)	C8—C9	1.526 (5)
O2—C7	1.217 (4)	C8—H8A	0.9700
F1—C16	1.328 (5)	C8—H8B	0.9700
F2—C16	1.339 (5)	C9—C10	1.506 (5)
F3—C16	1.345 (5)	C9—H9	0.9800
C1—C2	1.389 (5)	C10—C15	1.391 (5)
C1—C6	1.392 (5)	C10—C11	1.392 (5)
C2—C3	1.359 (5)	C11—C12	1.390 (6)
C2—H2	0.9300	C11—C16	1.480 (7)
C3—C4	1.390 (5)	C12—C13	1.367 (6)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.367 (5)	C13—C14	1.361 (6)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.401 (5)	C14—C15	1.397 (6)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.468 (5)	C15—H15	0.9300
C1—O1—C9	115.2 (3)	O1—C9—C8	109.8 (3)
O1—C1—C2	116.5 (3)	C10—C9—C8	112.2 (3)
O1—C1—C6	122.3 (3)	O1—C9—H9	109.3
C2—C1—C6	121.2 (3)	C10—C9—H9	109.3
C3—C2—C1	119.6 (4)	C8—C9—H9	109.3
C3—C2—H2	120.2	C15—C10—C11	117.9 (4)
C1—C2—H2	120.2	C15—C10—C9	118.3 (4)
C2—C3—C4	121.0 (4)	C11—C10—C9	123.9 (4)
C2—C3—H3	119.5	C12—C11—C10	120.3 (4)
C4—C3—H3	119.5	C12—C11—C16	118.5 (4)
C5—C4—C3	119.1 (4)	C10—C11—C16	121.2 (4)
C5—C4—H4	120.4	C13—C12—C11	120.7 (5)
C3—C4—H4	120.4	C13—C12—H12	119.7
C4—C5—C6	121.8 (4)	C11—C12—H12	119.7
C4—C5—H5	119.1	C14—C13—C12	120.3 (5)
C6—C5—H5	119.1	C14—C13—H13	119.8
C1—C6—C5	117.3 (3)	C12—C13—H13	119.8
C1—C6—C7	120.8 (4)	C13—C14—C15	119.7 (5)
C5—C6—C7	121.6 (4)	C13—C14—H14	120.1
O2—C7—C6	123.2 (4)	C15—C14—H14	120.1
O2—C7—C8	122.3 (4)	C10—C15—C14	121.1 (4)
C6—C7—C8	114.5 (4)	C10—C15—H15	119.4
C7—C8—C9	111.0 (3)	C14—C15—H15	119.4
C7—C8—H8A	109.4	F1—C16—F2	106.4 (5)
C9—C8—H8A	109.4	F1—C16—F3	106.0 (4)
C7—C8—H8B	109.4	F2—C16—F3	104.9 (4)
C9—C8—H8B	109.4	F1—C16—C11	113.7 (4)
H8A—C8—H8B	108.0	F2—C16—C11	113.2 (4)
O1—C9—C10	106.9 (3)	F3—C16—C11	112.0 (5)
C9—O1—C1—C2	−158.8 (4)	C7—C8—C9—C10	176.3 (4)
C9—O1—C1—C6	21.0 (7)	O1—C9—C10—C15	43.2 (5)
O1—C1—C2—C3	−179.4 (5)	C8—C9—C10—C15	−77.3 (5)
C6—C1—C2—C3	0.7 (8)	O1—C9—C10—C11	−136.9 (4)
C1—C2—C3—C4	−1.8 (8)	C8—C9—C10—C11	102.7 (4)
C2—C3—C4—C5	2.2 (8)	C15—C10—C11—C12	1.7 (6)
C3—C4—C5—C6	−1.6 (8)	C9—C10—C11—C12	−178.2 (4)
O1—C1—C6—C5	−179.9 (4)	C15—C10—C11—C16	−178.1 (4)
C2—C1—C6—C5	−0.1 (7)	C9—C10—C11—C16	2.0 (6)
O1—C1—C6—C7	5.9 (7)	C10—C11—C12—C13	−1.4 (6)
C2—C1—C6—C7	−174.3 (5)	C16—C11—C12—C13	178.4 (4)
C4—C5—C6—C1	0.5 (8)	C11—C12—C13—C14	0.2 (7)
C4—C5—C6—C7	174.7 (5)	C12—C13—C14—C15	0.7 (7)
C1—C6—C7—O2	−179.4 (6)	C11—C10—C15—C14	−0.9 (6)
C5—C6—C7—O2	6.6 (9)	C9—C10—C15—C14	179.1 (4)
C1—C6—C7—C8	1.3 (7)	C13—C14—C15—C10	−0.3 (7)
C5—C6—C7—C8	−172.6 (5)	C12—C11—C16—F1	2.2 (7)
O2—C7—C8—C9	148.5 (5)	C10—C11—C16—F1	−178.0 (4)
C6—C7—C8—C9	−32.3 (6)	C12—C11—C16—F2	−119.4 (4)
C1—O1—C9—C10	−174.2 (4)	C10—C11—C16—F2	60.4 (6)
C1—O1—C9—C8	−52.2 (5)	C12—C11—C16—F3	122.3 (4)
C7—C8—C9—O1	57.6 (5)	C10—C11—C16—F3	−57.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···F2	0.98	2.36	3.068 (5)	129
C9—H9···F3	0.98	2.50	2.984 (5)	110
C12—H12···F1	0.93	2.33	2.677 (6)	102
C15—H15···O1	0.93	2.50	2.760 (5)	96
C3—H3···O2i	0.93	2.54	3.311 (5)	140
C5—H5···F3ii	0.93	2.54	3.313 (5)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.54	3.311 (5)	140
C5—H5⋯F3ii	0.93	2.54	3.313 (5)	141

Symmetry codes: (i) ; (ii) .