(1E,4E)-1,5-Bis[2-(trifluoro-meth-yl)phen-yl]penta-1,4-dien-3-one.

In the title compound, C(19)H(12)F(6)O, a monoketone derivative of curcumin, both double bonds have a trans conformation. The mol-ecule is mostly planar with all C and O atoms essentially coplanar, with the exception of one benzene ring, which is tilted by 17.18 (1)° with respect to the plane of the remainder of the mol-ecule. The r.m.s. deviation from planarity of the coplanar section is 0.0097 Å. The crystal packing features weak C-H⋯O and C-H⋯F inter-actions.

Related literature

For the synthesis of chalcones, see: Tully et al. (2001 ▶). For the biological properties of chalcones, see: Buescher & Yang (2000 ▶); Kumar et al. (2003 ▶), Hsu & Cheng (2007 ▶). For their physical properties, see: Fichou et al. (1988 ▶); Butcher et al. (2006 ▶). For similar structures, see: Butcher et al. (2007 ▶); Nizam Mohideen et al. (2007 ▶); Harrison et al. (2006 ▶).

Experimental

Crystal data

C19H12F6O

M = 370.29

Monoclinic,

a = 11.3123 (12) Å

b = 4.7907 (4) Å

c = 15.1697 (16) Å

β = 101.834 (3)°

V = 804.63 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.14 mm−1

T = 298 K

0.35 × 0.25 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.952, T max = 0.986

5185 measured reflections

2608 independent reflections

1931 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.096

S = 1.04

2608 reflections

235 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012) ▶; software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051586/zl2522sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051586/zl2522Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051586/zl2522Isup3.cml

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

C19H12F6O	F(000) = 376
Mr = 370.29	Dx = 1.528 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2360 reflections
a = 11.3123 (12) Å	θ = 2.7–24.1°
b = 4.7907 (4) Å	µ = 0.14 mm−1
c = 15.1697 (16) Å	T = 298 K
β = 101.834 (3)°	Block, colourless
V = 804.63 (14) Å3	0.35 × 0.25 × 0.10 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	2608 independent reflections
Radiation source: fine-focus sealed tube	1931 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
phi and ω scans	θmax = 27.8°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
Tmin = 0.952, Tmax = 0.986	k = −5→5
5185 measured reflections	l = −18→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0351P)2 + 0.2469P] where P = (Fo2 + 2Fc2)/3
2608 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.20 e Å−3
2 restraints	Δρmin = −0.14 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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
C1	1.1775 (4)	1.5554 (9)	1.1292 (2)	0.0761 (11)
H1	1.1342	1.5756	1.1747	0.091*
C2	1.2832 (4)	1.6949 (8)	1.1343 (2)	0.0784 (11)
H2	1.3110	1.8160	1.1819	0.094*
C3	1.3481 (3)	1.6560 (7)	1.0689 (2)	0.0673 (9)
H3	1.4220	1.7461	1.0736	0.081*
C4	1.3062 (3)	1.4847 (6)	0.9956 (2)	0.0501 (7)
C5	1.1957 (2)	1.3456 (6)	0.98898 (19)	0.0466 (7)
C6	1.1349 (3)	1.3854 (7)	1.0575 (2)	0.0619 (9)
H6	1.0619	1.2933	1.0549	0.074*
C7	1.3802 (3)	1.4515 (8)	0.9268 (2)	0.0654 (10)
C8	1.1460 (3)	1.1721 (7)	0.9110 (2)	0.0533 (8)
H8	1.1829	1.1877	0.8618	0.064*
C9	1.0547 (3)	0.9955 (7)	0.9024 (2)	0.0508 (8)
H9	1.0168	0.9688	0.9507	0.061*
C10	1.0119 (3)	0.8412 (7)	0.8190 (2)	0.0492 (7)
C11	0.9120 (3)	0.6426 (6)	0.81579 (19)	0.0505 (8)
H11	0.8802	0.6177	0.8671	0.061*
C12	0.8662 (3)	0.4996 (6)	0.7433 (2)	0.0478 (7)
H12	0.9004	0.5317	0.6934	0.057*
C13	0.7685 (2)	0.2965 (6)	0.73090 (18)	0.0420 (6)
C14	0.7286 (2)	0.1566 (6)	0.64946 (17)	0.0428 (7)
C15	0.6361 (3)	−0.0368 (6)	0.6405 (2)	0.0540 (8)
H15	0.6105	−0.1284	0.5859	0.065*
C16	0.5820 (3)	−0.0946 (7)	0.7110 (2)	0.0617 (9)
H16	0.5208	−0.2272	0.7047	0.074*
C17	0.6184 (3)	0.0439 (7)	0.7910 (2)	0.0595 (8)
H17	0.5806	0.0084	0.8388	0.071*
C18	0.7107 (3)	0.2348 (7)	0.80077 (19)	0.0518 (8)
H18	0.7351	0.3253	0.8557	0.062*
C19	0.7851 (3)	0.2061 (7)	0.5705 (2)	0.0578 (8)
F1	1.3299 (2)	1.5590 (5)	0.84801 (15)	0.0944 (7)
F2	1.4881 (2)	1.5699 (6)	0.94957 (17)	0.1057 (9)
F3	1.4031 (2)	1.1853 (6)	0.9114 (2)	0.1095 (9)
F4	0.7781 (2)	0.4718 (5)	0.54360 (14)	0.0860 (7)
F5	0.89964 (19)	0.1390 (5)	0.58521 (14)	0.0902 (7)
F6	0.7316 (2)	0.0638 (5)	0.49807 (13)	0.0954 (7)
O1	1.0559 (2)	0.8784 (5)	0.75344 (16)	0.0824 (8)

	U11	U22	U33	U12	U13	U23
C1	0.083 (3)	0.090 (3)	0.058 (2)	−0.016 (2)	0.0204 (19)	−0.011 (2)
C2	0.096 (3)	0.076 (3)	0.059 (2)	−0.025 (2)	0.005 (2)	−0.0118 (19)
C3	0.063 (2)	0.073 (2)	0.060 (2)	−0.0199 (18)	−0.0003 (17)	0.0054 (19)
C4	0.0462 (15)	0.0481 (18)	0.0545 (18)	−0.0042 (14)	0.0065 (13)	0.0089 (15)
C5	0.0479 (17)	0.0427 (17)	0.0481 (17)	0.0016 (13)	0.0076 (14)	0.0024 (14)
C6	0.061 (2)	0.068 (2)	0.058 (2)	−0.0144 (16)	0.0168 (16)	−0.0079 (17)
C7	0.057 (2)	0.067 (3)	0.073 (2)	−0.0142 (19)	0.0140 (17)	−0.0020 (19)
C8	0.0503 (17)	0.054 (2)	0.0572 (19)	−0.0016 (15)	0.0149 (14)	−0.0019 (15)
C9	0.0577 (18)	0.0486 (18)	0.0474 (17)	−0.0004 (14)	0.0138 (14)	−0.0002 (13)
C10	0.0544 (18)	0.0456 (19)	0.0466 (17)	0.0013 (14)	0.0080 (14)	−0.0025 (14)
C11	0.0614 (19)	0.0500 (19)	0.0408 (17)	−0.0002 (15)	0.0124 (14)	−0.0058 (13)
C12	0.0562 (18)	0.0440 (18)	0.0439 (16)	−0.0005 (14)	0.0119 (14)	−0.0004 (13)
C13	0.0470 (15)	0.0385 (16)	0.0404 (15)	0.0054 (13)	0.0089 (12)	−0.0002 (12)
C14	0.0504 (16)	0.0353 (16)	0.0416 (16)	0.0080 (13)	0.0070 (13)	−0.0015 (12)
C15	0.0589 (18)	0.0463 (18)	0.0511 (18)	0.0045 (16)	−0.0021 (15)	−0.0066 (15)
C16	0.0523 (18)	0.056 (2)	0.074 (2)	−0.0040 (16)	0.0067 (16)	0.0041 (17)
C17	0.0603 (19)	0.060 (2)	0.062 (2)	0.0020 (17)	0.0219 (16)	0.0124 (17)
C18	0.0622 (19)	0.0524 (19)	0.0420 (17)	−0.0007 (15)	0.0134 (14)	−0.0028 (14)
C19	0.070 (2)	0.056 (2)	0.0466 (19)	0.0075 (17)	0.0097 (16)	−0.0062 (16)
F1	0.1087 (16)	0.114 (2)	0.0642 (14)	−0.0084 (15)	0.0272 (12)	0.0071 (13)
F2	0.0714 (14)	0.133 (2)	0.120 (2)	−0.0401 (15)	0.0359 (13)	−0.0138 (16)
F3	0.1025 (17)	0.0725 (17)	0.176 (3)	0.0065 (13)	0.0802 (17)	−0.0137 (16)
F4	0.135 (2)	0.0631 (15)	0.0670 (12)	0.0083 (14)	0.0377 (12)	0.0116 (11)
F5	0.0785 (14)	0.1231 (19)	0.0772 (13)	0.0270 (13)	0.0352 (11)	−0.0012 (14)
F6	0.1393 (18)	0.0984 (17)	0.0467 (11)	−0.0143 (15)	0.0144 (12)	−0.0244 (12)
O1	0.0925 (18)	0.0963 (19)	0.0667 (16)	−0.0401 (16)	0.0356 (14)	−0.0247 (14)

C1—C2	1.358 (5)	C10—C11	1.470 (4)
C1—C6	1.366 (5)	C11—C12	1.310 (4)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.362 (5)	C12—C13	1.456 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.385 (4)	C13—C18	1.386 (4)
C3—H3	0.9300	C13—C14	1.397 (4)
C4—C5	1.401 (4)	C14—C15	1.383 (4)
C4—C7	1.474 (5)	C14—C19	1.488 (4)
C5—C6	1.372 (4)	C15—C16	1.364 (4)
C5—C8	1.460 (4)	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.371 (5)
C7—F1	1.318 (4)	C16—H16	0.9300
C7—F2	1.326 (4)	C17—C18	1.373 (4)
C7—F3	1.331 (4)	C17—H17	0.9300
C8—C9	1.321 (4)	C18—H18	0.9300
C8—H8	0.9300	C19—F5	1.309 (4)
C9—C10	1.460 (4)	C19—F6	1.329 (4)
C9—H9	0.9300	C19—F4	1.334 (4)
C10—O1	1.213 (4)
C2—C1—C6	120.1 (4)	C9—C10—C11	118.2 (3)
C2—C1—H1	119.9	C12—C11—C10	122.4 (3)
C6—C1—H1	119.9	C12—C11—H11	118.8
C1—C2—C3	119.4 (3)	C10—C11—H11	118.8
C1—C2—H2	120.3	C11—C12—C13	128.1 (3)
C3—C2—H2	120.3	C11—C12—H12	115.9
C2—C3—C4	121.2 (3)	C13—C12—H12	115.9
C2—C3—H3	119.4	C18—C13—C14	117.2 (3)
C4—C3—H3	119.4	C18—C13—C12	120.6 (2)
C3—C4—C5	119.5 (3)	C14—C13—C12	122.3 (3)
C3—C4—C7	118.8 (3)	C15—C14—C13	120.6 (3)
C5—C4—C7	121.7 (3)	C15—C14—C19	118.0 (3)
C6—C5—C4	117.3 (3)	C13—C14—C19	121.4 (3)
C6—C5—C8	121.5 (3)	C16—C15—C14	120.8 (3)
C4—C5—C8	121.2 (3)	C16—C15—H15	119.6
C1—C6—C5	122.4 (3)	C14—C15—H15	119.6
C1—C6—H6	118.8	C15—C16—C17	119.6 (3)
C5—C6—H6	118.8	C15—C16—H16	120.2
F1—C7—F2	105.8 (3)	C17—C16—H16	120.2
F1—C7—F3	106.2 (3)	C16—C17—C18	120.1 (3)
F2—C7—F3	104.7 (3)	C16—C17—H17	120.0
F1—C7—C4	113.4 (3)	C18—C17—H17	120.0
F2—C7—C4	113.3 (3)	C17—C18—C13	121.8 (3)
F3—C7—C4	112.7 (3)	C17—C18—H18	119.1
C9—C8—C5	127.5 (3)	C13—C18—H18	119.1
C9—C8—H8	116.3	F5—C19—F6	106.4 (3)
C5—C8—H8	116.3	F5—C19—F4	106.3 (3)
C8—C9—C10	121.6 (3)	F6—C19—F4	104.4 (3)
C8—C9—H9	119.2	F5—C19—C14	113.4 (3)
C10—C9—H9	119.2	F6—C19—C14	112.7 (3)
O1—C10—C9	121.2 (3)	F4—C19—C14	112.9 (3)
O1—C10—C11	120.7 (3)
C6—C1—C2—C3	−2.3 (6)	O1—C10—C11—C12	−0.3 (5)
C1—C2—C3—C4	2.4 (6)	C9—C10—C11—C12	178.6 (3)
C2—C3—C4—C5	−0.9 (5)	C10—C11—C12—C13	179.6 (3)
C2—C3—C4—C7	179.7 (4)	C11—C12—C13—C18	0.5 (4)
C3—C4—C5—C6	−0.7 (4)	C11—C12—C13—C14	−179.6 (3)
C7—C4—C5—C6	178.6 (3)	C18—C13—C14—C15	−0.7 (4)
C3—C4—C5—C8	177.5 (3)	C12—C13—C14—C15	179.5 (3)
C7—C4—C5—C8	−3.1 (4)	C18—C13—C14—C19	−179.5 (3)
C2—C1—C6—C5	0.7 (6)	C12—C13—C14—C19	0.6 (4)
C4—C5—C6—C1	0.8 (5)	C13—C14—C15—C16	0.0 (4)
C8—C5—C6—C1	−177.4 (3)	C19—C14—C15—C16	178.9 (3)
C3—C4—C7—F1	−113.3 (3)	C14—C15—C16—C17	1.1 (5)
C5—C4—C7—F1	67.3 (4)	C15—C16—C17—C18	−1.5 (5)
C3—C4—C7—F2	7.4 (5)	C16—C17—C18—C13	0.8 (5)
C5—C4—C7—F2	−172.0 (3)	C14—C13—C18—C17	0.2 (4)
C3—C4—C7—F3	126.0 (3)	C12—C13—C18—C17	−179.9 (3)
C5—C4—C7—F3	−53.4 (4)	C15—C14—C19—F5	−117.0 (3)
C6—C5—C8—C9	−13.8 (5)	C13—C14—C19—F5	61.9 (4)
C4—C5—C8—C9	168.1 (3)	C15—C14—C19—F6	4.0 (4)
C5—C8—C9—C10	178.0 (3)	C13—C14—C19—F6	−177.1 (3)
C8—C9—C10—O1	−2.9 (5)	C15—C14—C19—F4	121.9 (3)
C8—C9—C10—C11	178.3 (3)	C13—C14—C19—F4	−59.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···F3i	0.93	2.62	3.399 (4)	141 (2)
C1—H1···O1ii	0.93	2.72	3.290 (5)	121 (1)
C3—H3···Cg1	0.93	3.32 (2)	4.096 (3)	142 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯F3i	0.93	2.62	3.399 (4)	141 (2)
C1—H1⋯O1ii	0.93	2.72	3.290 (5)	121 (1)

Symmetry codes: (i) ; (ii) .