(6Z)-3,5-Bis(4-fluoro-phen-yl)-6-(1-hy-droxy-ethyl-idene)cyclo-hex-2-en-1-one.

In the title compound, C(20)H(16)F(2)O(2), the cyclo-hex-2-en-1-one ring adopts a distorted envelope conformation and the dihedral angles between its six-atom mean plane and the fluorophenyl rings are 38.9(8) and 82.3(1)°. The two fluoro-phenyl rings are oriented at an angle of 77.3 (3)°. The long hy-droxy O-H bond length of 1.22 (3) and the H⋯O distance of 1.28 (3) Å, together with a longer than expected C=O bond length [1.290 (2) Å] in the hy-droxy(en-1-one) group, indicate sharing of the H atom as O⋯H⋯O between the two O atoms and the influence of electron delocalization. Weak C-H⋯O inter-molecular inter-actions form an infinite two-dimensional network in (011).

Related literature

For biological applications of some cyclo­hexenones, see: Eddington et al. (2000 ▶); Kolesnick & Golde (1994 ▶). For background to the applications of cyclo­hexenones, see: Padmavathi et al. (1999 ▶, 2000 ▶); Padmavathi, Sharmila, Somashekara Reddy & Bhaskar Reddy (2001 ▶); Padmavathi, Sharmila, Balaiah et al. (2001 ▶). For related structures, see: Fischer et al. (2008 ▶); Li et al. (2009 ▶); Dutkiewicz et al. (2011 ▶). For the various derivatives of 4,4-difluoro­chalcone, see: Fun et al. (2010 ▶); Jasinski et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C20H16F2O2

M = 326.33

Monoclinic,

a = 17.663 (2) Å

b = 6.2371 (6) Å

c = 15.2357 (16) Å

β = 107.717 (13)°

V = 1598.9 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.85 mm−1

T = 173 K

0.35 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.754, T max = 0.862

5441 measured reflections

3023 independent reflections

2154 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.147

S = 1.02

3023 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED; 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: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003078/gg2071sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003078/gg2071Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003078/gg2071Isup3.cml

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

C20H16F2O2	F(000) = 680
Mr = 326.33	Dx = 1.356 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1763 reflections
a = 17.663 (2) Å	θ = 3.4–70.8°
b = 6.2371 (6) Å	µ = 0.85 mm−1
c = 15.2357 (16) Å	T = 173 K
β = 107.717 (13)°	Block, yellow
V = 1598.9 (3) Å3	0.35 × 0.20 × 0.18 mm
Z = 4

Oxford Diffraction Xcalibur Gemini diffractometer	3023 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2154 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 16.1500 pixels mm-1	θmax = 70.7°, θmin = 5.3°
ω scans	h = −21→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −7→7
Tmin = 0.754, Tmax = 0.862	l = −18→18
5441 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0646P)2 + 0.2155P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3023 reflections	Δρmax = 0.17 e Å−3
222 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0017 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.55493 (10)	0.1856 (4)	0.43446 (11)	0.1300 (7)
F2	0.01595 (9)	0.2581 (3)	0.48620 (11)	0.0984 (5)
O1	0.26793 (10)	0.4978 (3)	−0.05192 (11)	0.0813 (5)
H1	0.2297 (15)	0.605 (5)	−0.0137 (19)	0.098*
O2	0.19432 (10)	0.6694 (2)	0.04310 (11)	0.0785 (5)
C1	0.32971 (15)	0.1596 (5)	−0.01899 (18)	0.0895 (8)
H1A	0.3318	0.1788	−0.0820	0.134*
H1B	0.3059	0.0201	−0.0137	0.134*
H1C	0.3837	0.1657	0.0241	0.134*
C2	0.28083 (13)	0.3328 (4)	0.00327 (15)	0.0666 (6)
C3	0.25062 (12)	0.3242 (3)	0.07759 (13)	0.0585 (5)
C4	0.20637 (13)	0.4997 (3)	0.09387 (14)	0.0610 (5)
C5	0.17204 (13)	0.4938 (3)	0.16889 (15)	0.0622 (5)
H5A	0.1539	0.6235	0.1882	0.075*
C6	0.16517 (11)	0.3107 (3)	0.21179 (14)	0.0552 (5)
C7	0.19511 (12)	0.1060 (3)	0.18191 (16)	0.0610 (5)
H7A	0.1511	0.0375	0.1336	0.073*
H7B	0.2112	0.0069	0.2351	0.073*
C8	0.26582 (12)	0.1378 (3)	0.14426 (14)	0.0591 (5)
H8A	0.2699	0.0058	0.1087	0.071*
C9	0.34407 (12)	0.1584 (3)	0.22286 (14)	0.0598 (5)
C10	0.37064 (15)	−0.0158 (4)	0.28156 (16)	0.0741 (6)
H10A	0.3398	−0.1434	0.2722	0.089*
C11	0.44143 (16)	−0.0060 (5)	0.35355 (18)	0.0892 (8)
H11A	0.4591	−0.1247	0.3937	0.107*
C12	0.48489 (16)	0.1786 (6)	0.36503 (17)	0.0879 (8)
C13	0.46193 (14)	0.3517 (5)	0.31003 (16)	0.0805 (7)
H13A	0.4936	0.4778	0.3198	0.097*
C14	0.39064 (13)	0.3403 (4)	0.23873 (15)	0.0692 (6)
H14A	0.3736	0.4614	0.1999	0.083*
C15	0.12484 (11)	0.2989 (3)	0.28353 (13)	0.0544 (5)
C16	0.08461 (12)	0.1136 (4)	0.29494 (15)	0.0623 (5)
H16A	0.0831	−0.0058	0.2557	0.075*
C17	0.04699 (12)	0.1000 (4)	0.36192 (16)	0.0674 (6)
H17A	0.0191	−0.0262	0.3686	0.081*
C18	0.05082 (13)	0.2727 (4)	0.41839 (15)	0.0680 (6)
C19	0.08926 (13)	0.4591 (4)	0.41012 (15)	0.0679 (6)
H19A	0.0906	0.5769	0.4501	0.081*
C20	0.12583 (12)	0.4709 (3)	0.34258 (14)	0.0616 (5)
H20A	0.1525	0.5994	0.3359	0.074*

	U11	U22	U33	U12	U13	U23
F1	0.0915 (11)	0.195 (2)	0.0799 (10)	0.0137 (13)	−0.0091 (9)	0.0144 (12)
F2	0.1129 (12)	0.1062 (11)	0.0963 (10)	−0.0046 (9)	0.0622 (9)	−0.0015 (9)
O1	0.0858 (11)	0.0952 (12)	0.0606 (9)	−0.0078 (10)	0.0188 (8)	0.0136 (9)
O2	0.0991 (12)	0.0610 (9)	0.0726 (10)	0.0020 (8)	0.0222 (9)	0.0133 (8)
C1	0.0811 (16)	0.114 (2)	0.0818 (16)	0.0050 (16)	0.0377 (14)	0.0018 (16)
C2	0.0587 (12)	0.0782 (15)	0.0583 (12)	−0.0082 (11)	0.0110 (10)	−0.0009 (11)
C3	0.0593 (11)	0.0602 (12)	0.0532 (11)	−0.0066 (9)	0.0130 (9)	−0.0014 (9)
C4	0.0672 (12)	0.0521 (11)	0.0569 (11)	−0.0050 (10)	0.0087 (10)	0.0021 (9)
C5	0.0696 (13)	0.0493 (11)	0.0672 (12)	0.0017 (10)	0.0200 (11)	−0.0023 (10)
C6	0.0528 (10)	0.0474 (10)	0.0614 (11)	−0.0019 (8)	0.0113 (9)	−0.0038 (9)
C7	0.0647 (12)	0.0495 (11)	0.0703 (13)	−0.0029 (9)	0.0225 (10)	−0.0011 (10)
C8	0.0645 (12)	0.0528 (11)	0.0621 (11)	0.0017 (9)	0.0225 (10)	−0.0034 (9)
C9	0.0639 (12)	0.0647 (12)	0.0561 (11)	0.0101 (10)	0.0263 (10)	0.0025 (10)
C10	0.0818 (16)	0.0723 (15)	0.0732 (14)	0.0130 (12)	0.0310 (13)	0.0104 (12)
C11	0.0948 (19)	0.105 (2)	0.0696 (15)	0.0321 (17)	0.0283 (15)	0.0231 (15)
C12	0.0720 (15)	0.130 (2)	0.0589 (13)	0.0129 (17)	0.0151 (12)	0.0062 (16)
C13	0.0727 (14)	0.103 (2)	0.0624 (13)	−0.0063 (14)	0.0154 (12)	0.0002 (14)
C14	0.0668 (13)	0.0773 (15)	0.0614 (12)	−0.0020 (12)	0.0163 (11)	0.0054 (11)
C15	0.0495 (10)	0.0526 (11)	0.0579 (11)	0.0015 (8)	0.0116 (9)	0.0009 (9)
C16	0.0587 (11)	0.0585 (12)	0.0675 (12)	−0.0046 (10)	0.0162 (10)	−0.0061 (10)
C17	0.0566 (12)	0.0648 (13)	0.0809 (14)	−0.0065 (10)	0.0211 (11)	0.0025 (12)
C18	0.0630 (13)	0.0781 (15)	0.0647 (13)	0.0053 (11)	0.0220 (11)	0.0033 (12)
C19	0.0740 (14)	0.0657 (13)	0.0635 (12)	−0.0004 (11)	0.0202 (11)	−0.0071 (11)
C20	0.0633 (12)	0.0546 (11)	0.0626 (12)	−0.0031 (9)	0.0125 (10)	−0.0026 (10)

F1—C12	1.362 (3)	C8—H8A	1.0000
F2—C18	1.357 (2)	C9—C14	1.379 (3)
O1—C2	1.304 (3)	C9—C10	1.394 (3)
O1—H1	1.22 (3)	C10—C11	1.391 (3)
O2—C4	1.290 (2)	C10—H10A	0.9500
O2—H1	1.28 (3)	C11—C12	1.365 (4)
C1—C2	1.485 (3)	C11—H11A	0.9500
C1—H1A	0.9800	C12—C13	1.351 (4)
C1—H1B	0.9800	C13—C14	1.392 (3)
C1—H1C	0.9800	C13—H13A	0.9500
C2—C3	1.392 (3)	C14—H14A	0.9500
C3—C4	1.410 (3)	C15—C16	1.395 (3)
C3—C8	1.513 (3)	C15—C20	1.397 (3)
C4—C5	1.448 (3)	C16—C17	1.380 (3)
C5—C6	1.339 (3)	C16—H16A	0.9500
C5—H5A	0.9500	C17—C18	1.367 (3)
C6—C15	1.477 (3)	C17—H17A	0.9500
C6—C7	1.505 (3)	C18—C19	1.371 (3)
C7—C8	1.538 (3)	C19—C20	1.373 (3)
C7—H7A	0.9900	C19—H19A	0.9500
C7—H7B	0.9900	C20—H20A	0.9500
C8—C9	1.534 (3)
C2—O1—H1	98.0 (12)	C14—C9—C8	123.59 (19)
C4—O2—H1	97.0 (12)	C10—C9—C8	118.9 (2)
C2—C1—H1A	109.5	C11—C10—C9	121.2 (2)
C2—C1—H1B	109.5	C11—C10—H10A	119.4
H1A—C1—H1B	109.5	C9—C10—H10A	119.4
C2—C1—H1C	109.5	C12—C11—C10	118.3 (2)
H1A—C1—H1C	109.5	C12—C11—H11A	120.9
H1B—C1—H1C	109.5	C10—C11—H11A	120.9
O1—C2—C3	121.3 (2)	C13—C12—F1	119.1 (3)
O1—C2—C1	115.2 (2)	C13—C12—C11	122.9 (3)
C3—C2—C1	123.4 (2)	F1—C12—C11	118.0 (3)
C2—C3—C4	118.9 (2)	C12—C13—C14	118.2 (3)
C2—C3—C8	122.8 (2)	C12—C13—H13A	120.9
C4—C3—C8	118.23 (18)	C14—C13—H13A	120.9
O2—C4—C3	122.1 (2)	C9—C14—C13	121.9 (2)
O2—C4—C5	117.5 (2)	C9—C14—H14A	119.1
C3—C4—C5	120.43 (19)	C13—C14—H14A	119.1
C6—C5—C4	121.92 (19)	C16—C15—C20	117.58 (19)
C6—C5—H5A	119.0	C16—C15—C6	120.81 (18)
C4—C5—H5A	119.0	C20—C15—C6	121.61 (18)
C5—C6—C15	122.64 (18)	C17—C16—C15	121.4 (2)
C5—C6—C7	118.91 (19)	C17—C16—H16A	119.3
C15—C6—C7	118.34 (17)	C15—C16—H16A	119.3
C6—C7—C8	113.80 (17)	C18—C17—C16	118.3 (2)
C6—C7—H7A	108.8	C18—C17—H17A	120.9
C8—C7—H7A	108.8	C16—C17—H17A	120.9
C6—C7—H7B	108.8	F2—C18—C17	118.6 (2)
C8—C7—H7B	108.8	F2—C18—C19	118.6 (2)
H7A—C7—H7B	107.7	C17—C18—C19	122.8 (2)
C3—C8—C9	113.18 (17)	C18—C19—C20	118.3 (2)
C3—C8—C7	110.55 (17)	C18—C19—H19A	120.9
C9—C8—C7	111.15 (17)	C20—C19—H19A	120.9
C3—C8—H8A	107.2	C19—C20—C15	121.6 (2)
C9—C8—H8A	107.2	C19—C20—H20A	119.2
C7—C8—H8A	107.2	C15—C20—H20A	119.2
C14—C9—C10	117.5 (2)
O1—C2—C3—C4	−1.1 (3)	C14—C9—C10—C11	0.1 (3)
C1—C2—C3—C4	178.5 (2)	C8—C9—C10—C11	179.6 (2)
O1—C2—C3—C8	−178.63 (18)	C9—C10—C11—C12	−0.5 (4)
C1—C2—C3—C8	1.0 (3)	C10—C11—C12—C13	0.4 (4)
C2—C3—C4—O2	−1.3 (3)	C10—C11—C12—F1	−178.7 (2)
C8—C3—C4—O2	176.34 (18)	F1—C12—C13—C14	179.2 (2)
C2—C3—C4—C5	178.17 (19)	C11—C12—C13—C14	0.1 (4)
C8—C3—C4—C5	−4.2 (3)	C10—C9—C14—C13	0.4 (3)
O2—C4—C5—C6	164.4 (2)	C8—C9—C14—C13	−179.0 (2)
C3—C4—C5—C6	−15.1 (3)	C12—C13—C14—C9	−0.5 (4)
C4—C5—C6—C15	−175.21 (18)	C5—C6—C15—C16	148.4 (2)
C4—C5—C6—C7	0.9 (3)	C7—C6—C15—C16	−27.7 (3)
C5—C6—C7—C8	30.3 (3)	C5—C6—C15—C20	−32.0 (3)
C15—C6—C7—C8	−153.45 (17)	C7—C6—C15—C20	151.90 (19)
C2—C3—C8—C9	85.6 (2)	C20—C15—C16—C17	0.1 (3)
C4—C3—C8—C9	−91.9 (2)	C6—C15—C16—C17	179.70 (18)
C2—C3—C8—C7	−148.96 (19)	C15—C16—C17—C18	−0.9 (3)
C4—C3—C8—C7	33.5 (2)	C16—C17—C18—F2	−178.07 (18)
C6—C7—C8—C3	−45.8 (2)	C16—C17—C18—C19	1.1 (3)
C6—C7—C8—C9	80.8 (2)	F2—C18—C19—C20	178.66 (19)
C3—C8—C9—C14	8.3 (3)	C17—C18—C19—C20	−0.5 (3)
C7—C8—C9—C14	−116.8 (2)	C18—C19—C20—C15	−0.3 (3)
C3—C8—C9—C10	−171.12 (18)	C16—C15—C20—C19	0.5 (3)
C7—C8—C9—C10	63.8 (2)	C6—C15—C20—C19	−179.09 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	1.22 (3)	1.28 (3)	2.465 (2)	163 (2)
C8—H8A···O2i	1.00	2.52	3.365 (3)	142
C19—H19A···O2ii	0.95	2.51	3.260 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1⋯H1⋯O2	1.22 (3)	1.28 (3)	2.465 (2)	163 (2)
C8—H8A⋯O2i	1.00	2.52	3.365 (3)	142
C19—H19A⋯O2ii	0.95	2.51	3.260 (3)	136

Symmetry codes: (i) ; (ii) .