(2Z,4E)-1-(5-Fluoro-2-hy-droxy-phen-yl)-5-(4-fluoro-phen-yl)-3-hy-droxy-penta-2,4-dien-1-one.

In the title mol-ecule, C17H12F2O3, the dihedral angle between the benzene rings is 8.6 (2)°. In the crystal, two pairs of O-H⋯O hydrogen bonds connect the mol-ecules into inversion dimers. In addition, weak C-H⋯F hydrogen bonds link the dimers into a two-dimensional network parallel to (10-4). The carbonyl O atom is an acceptor for two weak intra-molecular hydrogen bonds.

Related literature

For the biological activities of chalcones, see: Meng et al. (2007 ▶); Schobert et al. (2009 ▶). For the synthesis, see: Baker (1933 ▶); Mahal & Venkataraman (1934 ▶). For a related structure, see: Fun et al. (2012 ▶).

Experimental

Crystal data

C17H12F2O3

M = 302.27

Monoclinic,

a = 6.8275 (18) Å

b = 14.004 (4) Å

c = 14.267 (4) Å

β = 91.293 (5)°

V = 1363.8 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 173 K

0.32 × 0.23 × 0.18 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.963, T max = 0.979

6787 measured reflections

2392 independent reflections

2040 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.147

S = 1.08

2392 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813033564/lh5672sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033564/lh5672Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033564/lh5672Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H12F2O3	F(000) = 624
Mr = 302.27	Dx = 1.472 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2113 reflections
a = 6.8275 (18) Å	θ = 1.6–27.3°
b = 14.004 (4) Å	µ = 0.12 mm−1
c = 14.267 (4) Å	T = 173 K
β = 91.293 (5)°	Block, yellow
V = 1363.8 (7) Å3	0.32 × 0.23 × 0.18 mm
Z = 4

Bruker APEX CCD diffractometer	2392 independent reflections
Radiation source: fine-focus sealed tube	2040 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scan	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
Tmin = 0.963, Tmax = 0.979	k = −16→16
6787 measured reflections	l = −12→16

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.073P)2 + 0.3861P] where P = (Fo2 + 2Fc2)/3
2392 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.29 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
F1	−1.0830 (2)	1.43310 (10)	0.38367 (11)	0.0579 (5)
F2	−1.6953 (2)	0.59884 (10)	0.25050 (10)	0.0577 (5)
O3	−0.7476 (2)	0.93089 (10)	0.42390 (11)	0.0383 (4)
H3A	−0.6598	0.9675	0.4404	0.057*
O2	−0.5856 (2)	1.09111 (10)	0.45331 (11)	0.0348 (4)
O1	−0.3972 (2)	1.24886 (10)	0.46202 (11)	0.0391 (4)
H1A	−0.4108	1.1908	0.4649	0.059*
C16	−1.5714 (3)	0.75182 (16)	0.27847 (15)	0.0371 (5)
H16A	−1.6915	0.7780	0.2602	0.045*
C6	−0.9127 (3)	1.38522 (15)	0.40188 (16)	0.0371 (5)
C9	−0.9017 (3)	0.98066 (14)	0.39432 (13)	0.0276 (5)
C1	−0.7404 (3)	1.13263 (14)	0.42564 (13)	0.0258 (5)
C7	−0.9178 (3)	1.28835 (15)	0.40533 (15)	0.0328 (5)
H7A	−1.0352	1.2559	0.3952	0.039*
C5	−0.7442 (4)	1.43672 (16)	0.41622 (16)	0.0401 (6)
H5A	−0.7455	1.5030	0.4127	0.048*
C13	−1.2171 (3)	0.67182 (15)	0.33270 (14)	0.0336 (5)
H13A	−1.0979	0.6447	0.3511	0.040*
C8	−0.9043 (3)	1.07757 (14)	0.39450 (14)	0.0287 (5)
H8A	−1.0170	1.1090	0.3736	0.034*
C3	−0.5709 (3)	1.28979 (15)	0.44117 (14)	0.0297 (5)
C14	−1.3700 (4)	0.61349 (16)	0.30486 (16)	0.0400 (6)
H14A	−1.3558	0.5474	0.3041	0.048*
C11	−1.0733 (3)	0.83020 (14)	0.36333 (14)	0.0287 (5)
H11A	−0.9613	0.7987	0.3852	0.034*
C2	−0.7438 (3)	1.23770 (14)	0.42429 (13)	0.0271 (5)
C17	−1.4183 (3)	0.80885 (16)	0.30625 (15)	0.0331 (5)
H17A	−1.4352	0.8747	0.3068	0.040*
C10	−1.0668 (3)	0.92464 (14)	0.36235 (14)	0.0294 (5)
H10A	−1.1766	0.9571	0.3394	0.035*
C15	−1.5432 (3)	0.65543 (17)	0.27832 (15)	0.0385 (6)
C12	−1.2379 (3)	0.77070 (14)	0.33372 (13)	0.0265 (5)
C4	−0.5740 (3)	1.38854 (15)	0.43586 (16)	0.0374 (6)
H4A	−0.4585	1.4226	0.4458	0.045*

	U11	U22	U33	U12	U13	U23
F1	0.0450 (9)	0.0381 (8)	0.0906 (12)	0.0127 (6)	0.0004 (8)	0.0083 (8)
F2	0.0554 (10)	0.0552 (9)	0.0619 (10)	−0.0309 (7)	−0.0138 (7)	−0.0001 (7)
O3	0.0275 (8)	0.0281 (8)	0.0588 (11)	0.0005 (6)	−0.0106 (7)	−0.0042 (7)
O2	0.0258 (8)	0.0298 (8)	0.0483 (9)	−0.0013 (6)	−0.0062 (7)	0.0013 (7)
O1	0.0295 (9)	0.0346 (8)	0.0530 (10)	−0.0088 (7)	−0.0058 (7)	0.0058 (7)
C16	0.0306 (12)	0.0444 (13)	0.0363 (13)	−0.0028 (10)	0.0002 (9)	−0.0039 (10)
C6	0.0374 (13)	0.0306 (11)	0.0434 (13)	0.0058 (10)	0.0033 (10)	0.0042 (10)
C9	0.0268 (11)	0.0301 (11)	0.0258 (11)	0.0005 (9)	−0.0012 (8)	0.0017 (8)
C1	0.0235 (10)	0.0308 (11)	0.0231 (10)	0.0005 (8)	0.0001 (8)	0.0016 (8)
C7	0.0307 (12)	0.0318 (11)	0.0358 (12)	−0.0020 (9)	0.0008 (9)	0.0010 (9)
C5	0.0508 (15)	0.0260 (11)	0.0438 (14)	−0.0027 (10)	0.0066 (11)	0.0006 (10)
C13	0.0369 (13)	0.0324 (11)	0.0313 (12)	−0.0010 (9)	0.0002 (9)	0.0019 (9)
C8	0.0251 (11)	0.0297 (11)	0.0310 (11)	−0.0015 (8)	−0.0066 (8)	0.0042 (9)
C3	0.0307 (12)	0.0315 (11)	0.0269 (11)	−0.0046 (9)	0.0012 (9)	0.0016 (9)
C14	0.0535 (15)	0.0282 (11)	0.0383 (13)	−0.0097 (11)	0.0018 (11)	−0.0012 (10)
C11	0.0271 (12)	0.0333 (11)	0.0257 (11)	0.0009 (9)	0.0005 (8)	−0.0027 (9)
C2	0.0305 (11)	0.0284 (11)	0.0224 (10)	−0.0028 (9)	0.0023 (8)	0.0013 (8)
C17	0.0296 (12)	0.0331 (11)	0.0367 (12)	−0.0009 (9)	0.0014 (9)	−0.0043 (9)
C10	0.0274 (11)	0.0316 (11)	0.0290 (11)	−0.0011 (9)	−0.0051 (9)	0.0000 (9)
C15	0.0398 (14)	0.0441 (13)	0.0317 (12)	−0.0205 (11)	−0.0008 (10)	−0.0013 (10)
C12	0.0299 (11)	0.0291 (10)	0.0206 (10)	−0.0032 (9)	0.0018 (8)	−0.0019 (8)
C4	0.0413 (14)	0.0312 (11)	0.0397 (13)	−0.0108 (10)	0.0026 (10)	−0.0030 (10)

F1—C6	1.362 (2)	C5—C4	1.368 (3)
F2—C15	1.358 (2)	C5—H5A	0.9300
O3—C9	1.323 (2)	C13—C14	1.377 (3)
O3—H3A	0.8200	C13—C12	1.392 (3)
O2—C1	1.262 (2)	C13—H13A	0.9300
O1—C3	1.345 (2)	C8—H8A	0.9300
O1—H1A	0.8200	C3—C4	1.385 (3)
C16—C15	1.363 (3)	C3—C2	1.404 (3)
C16—C17	1.367 (3)	C14—C15	1.366 (3)
C16—H16A	0.9300	C14—H14A	0.9300
C6—C7	1.358 (3)	C11—C10	1.323 (3)
C6—C5	1.369 (3)	C11—C12	1.454 (3)
C9—C8	1.357 (3)	C11—H11A	0.9300
C9—C10	1.439 (3)	C17—C12	1.391 (3)
C1—C8	1.422 (3)	C17—H17A	0.9300
C1—C2	1.472 (3)	C10—H10A	0.9300
C7—C2	1.404 (3)	C4—H4A	0.9300
C7—H7A	0.9300
C9—O3—H3A	109.5	O1—C3—C2	123.41 (18)
C3—O1—H1A	109.5	C4—C3—C2	119.84 (19)
C15—C16—C17	118.1 (2)	C15—C14—C13	118.1 (2)
C15—C16—H16A	120.9	C15—C14—H14A	121.0
C17—C16—H16A	120.9	C13—C14—H14A	121.0
C7—C6—F1	118.4 (2)	C10—C11—C12	126.55 (19)
C7—C6—C5	122.9 (2)	C10—C11—H11A	116.7
F1—C6—C5	118.66 (19)	C12—C11—H11A	116.7
O3—C9—C8	122.42 (18)	C3—C2—C7	118.35 (18)
O3—C9—C10	115.18 (17)	C3—C2—C1	120.26 (18)
C8—C9—C10	122.40 (18)	C7—C2—C1	121.38 (18)
O2—C1—C8	119.71 (18)	C16—C17—C12	121.6 (2)
O2—C1—C2	118.55 (17)	C16—C17—H17A	119.2
C8—C1—C2	121.72 (18)	C12—C17—H17A	119.2
C6—C7—C2	119.3 (2)	C11—C10—C9	124.61 (19)
C6—C7—H7A	120.4	C11—C10—H10A	117.7
C2—C7—H7A	120.4	C9—C10—H10A	117.7
C4—C5—C6	118.6 (2)	F2—C15—C16	118.1 (2)
C4—C5—H5A	120.7	F2—C15—C14	118.8 (2)
C6—C5—H5A	120.7	C16—C15—C14	123.1 (2)
C14—C13—C12	121.1 (2)	C17—C12—C13	117.98 (19)
C14—C13—H13A	119.5	C17—C12—C11	122.39 (18)
C12—C13—H13A	119.5	C13—C12—C11	119.63 (19)
C9—C8—C1	122.19 (19)	C5—C4—C3	121.0 (2)
C9—C8—H8A	118.9	C5—C4—H4A	119.5
C1—C8—H8A	118.9	C3—C4—H4A	119.5
O1—C3—C4	116.75 (18)
F1—C6—C7—C2	−179.82 (18)	C8—C1—C2—C7	9.5 (3)
C5—C6—C7—C2	0.0 (4)	C15—C16—C17—C12	0.0 (3)
C7—C6—C5—C4	−0.7 (4)	C12—C11—C10—C9	178.58 (19)
F1—C6—C5—C4	179.0 (2)	O3—C9—C10—C11	1.7 (3)
O3—C9—C8—C1	0.7 (3)	C8—C9—C10—C11	−178.0 (2)
C10—C9—C8—C1	−179.63 (18)	C17—C16—C15—F2	−179.84 (19)
O2—C1—C8—C9	0.8 (3)	C17—C16—C15—C14	0.2 (4)
C2—C1—C8—C9	179.13 (19)	C13—C14—C15—F2	179.86 (19)
C12—C13—C14—C15	−0.1 (3)	C13—C14—C15—C16	−0.2 (4)
O1—C3—C2—C7	178.50 (19)	C16—C17—C12—C13	−0.3 (3)
C4—C3—C2—C7	−2.1 (3)	C16—C17—C12—C11	179.90 (19)
O1—C3—C2—C1	−2.1 (3)	C14—C13—C12—C17	0.3 (3)
C4—C3—C2—C1	177.29 (19)	C14—C13—C12—C11	−179.87 (19)
C6—C7—C2—C3	1.4 (3)	C10—C11—C12—C17	−4.8 (3)
C6—C7—C2—C1	−177.92 (19)	C10—C11—C12—C13	175.4 (2)
O2—C1—C2—C3	8.5 (3)	C6—C5—C4—C3	0.1 (3)
C8—C1—C2—C3	−169.85 (18)	O1—C3—C4—C5	−179.18 (19)
O2—C1—C2—C7	−172.14 (18)	C2—C3—C4—C5	1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	1.84	2.558 (2)	145
O1—H1A···O3i	0.82	2.55	3.145 (2)	130
O3—H3A···O2	0.82	1.81	2.532 (2)	146
O3—H3A···O2i	0.82	2.38	2.856 (2)	118
C10—H10A···F2ii	0.93	2.51	3.326 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.82	1.84	2.558 (2)	145
O1—H1A⋯O3i	0.82	2.55	3.145 (2)	130
O3—H3A⋯O2	0.82	1.81	2.532 (2)	146
O3—H3A⋯O2i	0.82	2.38	2.856 (2)	118
C10—H10A⋯F2ii	0.93	2.51	3.326 (3)	147

Symmetry codes: (i) ; (ii) .