(E)-3-[4-(Di-fluoro-meth-oxy)-3-hy-droxy-phen-yl]-1-phenyl-prop-2-en-1-one.

In the title compound, C16H12F2O3, the plane of the phenyl ring makes a dihedral angle of 3.22 (8)° with that of the benzene ring. The mol-ecule has an E conformation about the C=C bond. In the crystal, mol-ecules are linked via pairs of O-H⋯O hydrogen bonds, forming inversion dimers which are further consolidated by a pair of C-H⋯O hydrogen bonds. The dimers are linked via C-H⋯O hydrogen bonds, forming columns along the b-axis direction.

Related literature

For the biological activity of chalcones, see: Di Carlo et al. (1999 ▶); Lin et al. (2002 ▶). For a related structure, see: Ranjith et al. (2010 ▶).

Experimental

Crystal data

C16H12F2O3

M = 290.26

Monoclinic,

a = 17.1880 (11) Å

b = 4.1124 (3) Å

c = 19.6699 (13) Å

β = 106.289 (4)°

V = 1334.54 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.966, T max = 0.977

12412 measured reflections

3328 independent reflections

2456 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.120

S = 1.03

3328 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011288/su2584sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011288/su2584Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011288/su2584Isup3.cml

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

C16H12F2O3	F(000) = 600
Mr = 290.26	Dx = 1.445 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3328 reflections
a = 17.1880 (11) Å	θ = 1.4–28.3°
b = 4.1124 (3) Å	µ = 0.12 mm−1
c = 19.6699 (13) Å	T = 293 K
β = 106.289 (4)°	Block, colourless
V = 1334.54 (16) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	3328 independent reflections
Radiation source: fine-focus sealed tube	2456 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −22→21
Tmin = 0.966, Tmax = 0.977	k = −5→5
12412 measured reflections	l = −26→23

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0528P)2 + 0.3218P] where P = (Fo2 + 2Fc2)/3
3328 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.18 e Å−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. #========================================================================= # 8. Refinement Data #========================================================================= 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 > 2sigma(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
C1	0.58013 (9)	0.9403 (4)	0.34909 (8)	0.0501 (4)
H1	0.5553	0.7323	0.3305	0.060*
C2	0.57744 (8)	1.0801 (3)	0.23416 (7)	0.0408 (3)
C3	0.52043 (8)	0.8962 (3)	0.18585 (7)	0.0406 (3)
C4	0.53484 (8)	0.8222 (4)	0.12164 (7)	0.0421 (3)
H4	0.4969	0.7001	0.0885	0.051*
C5	0.60481 (7)	0.9264 (3)	0.10571 (7)	0.0399 (3)
C6	0.66097 (8)	1.1133 (4)	0.15554 (7)	0.0459 (3)
H6	0.7078	1.1872	0.1457	0.055*
C7	0.64685 (9)	1.1882 (4)	0.21944 (8)	0.0478 (3)
H7	0.6843	1.3120	0.2527	0.057*
C8	0.61704 (8)	0.8271 (4)	0.03816 (7)	0.0443 (3)
H8	0.5763	0.6990	0.0094	0.053*
C9	0.67854 (8)	0.8960 (4)	0.01260 (7)	0.0471 (3)
H9	0.7203	1.0275	0.0388	0.057*
C10	0.68243 (8)	0.7696 (4)	−0.05624 (7)	0.0434 (3)
C11	0.75269 (8)	0.8529 (3)	−0.08315 (7)	0.0429 (3)
C12	0.75121 (10)	0.7547 (4)	−0.15079 (8)	0.0587 (4)
H12	0.7062	0.6441	−0.1785	0.070*
C13	0.81561 (11)	0.8191 (5)	−0.17761 (9)	0.0662 (5)
H13	0.8143	0.7488	−0.2229	0.079*
C14	0.88160 (10)	0.9868 (5)	−0.13757 (10)	0.0655 (5)
H14	0.9247	1.0326	−0.1560	0.079*
C15	0.88416 (10)	1.0869 (5)	−0.07064 (10)	0.0710 (5)
H15	0.9291	1.1997	−0.0435	0.085*
C16	0.81987 (9)	1.0202 (4)	−0.04329 (8)	0.0576 (4)
H16	0.8219	1.0885	0.0022	0.069*
O1	0.56344 (6)	1.1715 (2)	0.29861 (5)	0.0490 (3)
O2	0.45380 (6)	0.7923 (3)	0.20384 (5)	0.0547 (3)
H2	0.4253	0.6830	0.1715	0.082*
O3	0.62832 (6)	0.5935 (3)	−0.09091 (6)	0.0615 (3)
F1	0.65995 (7)	0.9098 (4)	0.37665 (6)	0.1057 (5)
F2	0.55249 (7)	1.0449 (3)	0.40166 (5)	0.0779 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0568 (8)	0.0515 (8)	0.0449 (7)	0.0069 (7)	0.0190 (6)	−0.0019 (6)
C2	0.0461 (7)	0.0362 (7)	0.0401 (6)	0.0061 (6)	0.0120 (5)	−0.0010 (5)
C3	0.0368 (6)	0.0450 (7)	0.0406 (6)	0.0024 (6)	0.0120 (5)	0.0022 (6)
C4	0.0366 (6)	0.0507 (8)	0.0384 (6)	−0.0055 (6)	0.0097 (5)	−0.0029 (6)
C5	0.0374 (6)	0.0424 (7)	0.0404 (6)	0.0006 (5)	0.0116 (5)	0.0038 (5)
C6	0.0398 (7)	0.0487 (8)	0.0508 (8)	−0.0063 (6)	0.0153 (6)	0.0009 (6)
C7	0.0480 (7)	0.0440 (8)	0.0486 (7)	−0.0067 (6)	0.0090 (6)	−0.0057 (6)
C8	0.0409 (7)	0.0521 (8)	0.0406 (7)	−0.0057 (6)	0.0124 (5)	0.0000 (6)
C9	0.0429 (7)	0.0560 (9)	0.0441 (7)	−0.0083 (6)	0.0150 (6)	−0.0016 (6)
C10	0.0395 (7)	0.0498 (8)	0.0419 (7)	−0.0032 (6)	0.0128 (5)	0.0042 (6)
C11	0.0420 (7)	0.0457 (8)	0.0436 (7)	0.0005 (6)	0.0165 (5)	0.0058 (6)
C12	0.0577 (9)	0.0730 (11)	0.0498 (8)	−0.0128 (8)	0.0224 (7)	−0.0035 (8)
C13	0.0730 (11)	0.0793 (12)	0.0581 (9)	−0.0036 (10)	0.0377 (8)	0.0019 (9)
C14	0.0554 (9)	0.0719 (11)	0.0814 (12)	0.0000 (8)	0.0394 (9)	0.0111 (10)
C15	0.0479 (9)	0.0908 (14)	0.0791 (12)	−0.0185 (9)	0.0258 (8)	−0.0072 (10)
C16	0.0483 (8)	0.0727 (11)	0.0551 (8)	−0.0111 (8)	0.0200 (7)	−0.0068 (8)
O1	0.0638 (6)	0.0415 (5)	0.0433 (5)	0.0093 (5)	0.0178 (4)	−0.0050 (4)
O2	0.0452 (5)	0.0768 (8)	0.0471 (5)	−0.0116 (5)	0.0214 (4)	−0.0088 (5)
O3	0.0530 (6)	0.0835 (8)	0.0511 (6)	−0.0251 (6)	0.0199 (5)	−0.0131 (6)
F1	0.0658 (7)	0.1779 (15)	0.0725 (7)	0.0482 (8)	0.0180 (5)	0.0333 (8)
F2	0.0913 (8)	0.0979 (8)	0.0562 (6)	0.0185 (6)	0.0402 (5)	−0.0023 (5)

C1—F2	1.3250 (16)	C8—H8	0.9300
C1—F1	1.3322 (18)	C9—C10	1.4693 (19)
C1—O1	1.3461 (18)	C9—H9	0.9300
C1—H1	0.9800	C10—O3	1.2244 (16)
C2—C7	1.378 (2)	C10—C11	1.4880 (17)
C2—C3	1.3830 (19)	C11—C16	1.383 (2)
C2—O1	1.4063 (16)	C11—C12	1.384 (2)
C3—O2	1.3589 (15)	C12—C13	1.379 (2)
C3—C4	1.3873 (18)	C12—H12	0.9300
C4—C5	1.3925 (17)	C13—C14	1.372 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.3974 (19)	C14—C15	1.368 (3)
C5—C8	1.4605 (18)	C14—H14	0.9300
C6—C7	1.380 (2)	C15—C16	1.385 (2)
C6—H6	0.9300	C15—H15	0.9300
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.3223 (18)	O2—H2	0.8200
F2—C1—F1	105.47 (13)	C8—C9—C10	121.50 (13)
F2—C1—O1	107.31 (12)	C8—C9—H9	119.3
F1—C1—O1	110.42 (14)	C10—C9—H9	119.3
F2—C1—H1	111.1	O3—C10—C9	119.92 (12)
F1—C1—H1	111.1	O3—C10—C11	120.23 (12)
O1—C1—H1	111.1	C9—C10—C11	119.85 (12)
C7—C2—C3	121.35 (12)	C16—C11—C12	118.51 (13)
C7—C2—O1	118.71 (12)	C16—C11—C10	122.99 (13)
C3—C2—O1	119.88 (12)	C12—C11—C10	118.50 (13)
O2—C3—C2	118.64 (12)	C13—C12—C11	120.78 (15)
O2—C3—C4	123.15 (12)	C13—C12—H12	119.6
C2—C3—C4	118.20 (12)	C11—C12—H12	119.6
C3—C4—C5	121.55 (12)	C14—C13—C12	120.00 (16)
C3—C4—H4	119.2	C14—C13—H13	120.0
C5—C4—H4	119.2	C12—C13—H13	120.0
C4—C5—C6	118.80 (12)	C15—C14—C13	120.14 (15)
C4—C5—C8	118.20 (12)	C15—C14—H14	119.9
C6—C5—C8	122.99 (12)	C13—C14—H14	119.9
C7—C6—C5	119.88 (12)	C14—C15—C16	120.01 (16)
C7—C6—H6	120.1	C14—C15—H15	120.0
C5—C6—H6	120.1	C16—C15—H15	120.0
C2—C7—C6	120.21 (13)	C11—C16—C15	120.55 (15)
C2—C7—H7	119.9	C11—C16—H16	119.7
C6—C7—H7	119.9	C15—C16—H16	119.7
C9—C8—C5	128.35 (13)	C1—O1—C2	114.90 (10)
C9—C8—H8	115.8	C3—O2—H2	109.5
C5—C8—H8	115.8
C7—C2—C3—O2	178.98 (13)	C8—C9—C10—C11	179.99 (14)
O1—C2—C3—O2	−3.68 (19)	O3—C10—C11—C16	−172.66 (15)
C7—C2—C3—C4	0.0 (2)	C9—C10—C11—C16	6.6 (2)
O1—C2—C3—C4	177.37 (12)	O3—C10—C11—C12	6.5 (2)
O2—C3—C4—C5	−178.42 (13)	C9—C10—C11—C12	−174.29 (14)
C2—C3—C4—C5	0.5 (2)	C16—C11—C12—C13	0.7 (3)
C3—C4—C5—C6	−0.8 (2)	C10—C11—C12—C13	−178.48 (15)
C3—C4—C5—C8	177.55 (13)	C11—C12—C13—C14	−1.1 (3)
C4—C5—C6—C7	0.7 (2)	C12—C13—C14—C15	0.9 (3)
C8—C5—C6—C7	−177.60 (14)	C13—C14—C15—C16	−0.3 (3)
C3—C2—C7—C6	−0.2 (2)	C12—C11—C16—C15	−0.1 (3)
O1—C2—C7—C6	−177.53 (12)	C10—C11—C16—C15	179.00 (16)
C5—C6—C7—C2	−0.2 (2)	C14—C15—C16—C11	−0.1 (3)
C4—C5—C8—C9	−179.68 (15)	F2—C1—O1—C2	−170.69 (12)
C6—C5—C8—C9	−1.4 (3)	F1—C1—O1—C2	74.84 (16)
C5—C8—C9—C10	178.56 (14)	C7—C2—O1—C1	−101.79 (16)
C8—C9—C10—O3	−0.8 (2)	C3—C2—O1—C1	80.80 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.82	1.96	2.7722 (16)	172
C4—H4···O3i	0.93	2.48	3.1940 (19)	134
C1—H1···O1ii	0.98	2.40	3.3022 (19)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.82	1.96	2.7722 (16)	172
C4—H4⋯O3i	0.93	2.48	3.1940 (19)	134
C1—H1⋯O1ii	0.98	2.40	3.3022 (19)	152

Symmetry codes: (i) ; (ii) .