(E)-3-(3,4-Di-fluoro-phen-yl)-1-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one.

In the title compound, C17H14F2O3, the dihedral angle between the benzene rings is 20.56 (8)° and the H atoms at the central propenone group are trans configured. One of the F atoms is disordered over two positions (occupancy ratio 0.57:0.43) and was refined using a split model. In the crystal, the molecules are linked into centrosymmetrical dimers and are further connected into a three-dimensional network via weak C-H⋯O interactions.

Related literature

For related structures, see: Peng et al.(2010 ▶); Wu et al. (2010 ▶, 2011 ▶, 2012b ▶). For background to and applications of chalcones, see: Boumendjel et al. (2008 ▶); Kumar et al. (2011 ▶); Wu et al. (2011 ▶, 2012a ▶); Zhang et al. (2011 ▶).

Experimental

Crystal data

C17H14F2O3

M = 304.28

Monoclinic,

a = 8.7444 (9) Å

b = 8.4832 (9) Å

c = 19.829 (2) Å

β = 94.053 (2)°

V = 1467.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.21 × 0.15 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.977, T max = 0.988

8592 measured reflections

2876 independent reflections

2121 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.129

S = 1.04

2876 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013767/nc2310sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013767/nc2310Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013767/nc2310Isup3.cml

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

C17H14F2O3	F(000) = 632
Mr = 304.28	Dx = 1.377 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.7444 (9) Å	Cell parameters from 2015 reflections
b = 8.4832 (9) Å	θ = 5.0–54.2°
c = 19.829 (2) Å	µ = 0.11 mm−1
β = 94.053 (2)°	T = 293 K
V = 1467.2 (3) Å3	Prismatic, colorless
Z = 4	0.21 × 0.15 × 0.11 mm

Bruker SMART CCD area-detector diffractometer	2876 independent reflections
Radiation source: fine-focus sealed tube	2121 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
phi and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.977, Tmax = 0.988	k = −10→10
8592 measured reflections	l = −24→20

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0703P)2 + 0.091P] where P = (Fo2 + 2Fc2)/3
2876 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.19 e Å−3
0 restraints	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	Occ. (<1)
F1	−0.0102 (2)	−0.0304 (3)	0.14625 (12)	0.0862 (7)	0.57
F1'	−0.1205 (3)	0.2840 (4)	−0.03983 (14)	0.0844 (9)	0.43
F2	−0.21164 (11)	0.07757 (14)	0.05038 (6)	0.0743 (4)
O1	0.67825 (13)	0.44604 (16)	0.07214 (6)	0.0643 (4)
O2	1.05520 (12)	0.37085 (16)	0.35153 (5)	0.0569 (3)
O3	1.13490 (13)	0.49922 (18)	0.24315 (6)	0.0711 (4)
C1	0.12377 (18)	0.3023 (2)	0.01589 (8)	0.0512 (4)
H1	0.1536	0.3772	−0.0148	0.061*
C2	−0.02383 (9)	0.24437 (11)	0.01024 (4)	0.0546 (4)
H2	−0.0955	0.2809	−0.0253	0.065*	0.57
C3	−0.06758 (9)	0.13470 (11)	0.05544 (4)	0.0520 (4)
C4	0.03440 (9)	0.08176 (11)	0.10642 (4)	0.0557 (4)
H4'	0.0024	0.0047	0.1379	0.067*	0.43
C5	0.18143 (9)	0.13853 (11)	0.11244 (4)	0.0520 (4)
H5	0.2498	0.1023	0.1471	0.062*
C6	0.22850 (16)	0.24987 (19)	0.06709 (8)	0.0431 (4)
C7	0.38359 (17)	0.3175 (2)	0.07232 (8)	0.0457 (4)
H7	0.4064	0.3889	0.0389	0.055*
C8	0.49391 (17)	0.2877 (2)	0.11943 (8)	0.0505 (4)
H8	0.4769	0.2139	0.1528	0.061*
C9	0.64366 (17)	0.3684 (2)	0.12068 (8)	0.0474 (4)
C10	0.74973 (16)	0.35850 (19)	0.18235 (8)	0.0441 (4)
C11	0.71003 (19)	0.2904 (2)	0.24136 (9)	0.0588 (5)
H11	0.6145	0.2429	0.2426	0.071*
C12	0.80881 (19)	0.2909 (2)	0.29899 (9)	0.0587 (5)
H12	0.7792	0.2439	0.3384	0.070*
C13	0.95050 (17)	0.36056 (19)	0.29820 (8)	0.0459 (4)
C14	0.99356 (16)	0.42987 (19)	0.23785 (8)	0.0458 (4)
C15	0.89489 (17)	0.42856 (18)	0.18126 (8)	0.0449 (4)
H15	0.9242	0.4746	0.1416	0.054*
C16	1.0133 (2)	0.3151 (3)	0.41527 (9)	0.0700 (6)
H16A	0.9196	0.3648	0.4263	0.105*
H16B	1.0931	0.3399	0.4494	0.105*
H16C	0.9990	0.2030	0.4132	0.105*
C17	1.1804 (2)	0.5882 (3)	0.18825 (10)	0.0762 (6)
H17A	1.1838	0.5214	0.1493	0.114*
H17B	1.2802	0.6320	0.1993	0.114*
H17C	1.1083	0.6719	0.1786	0.114*

	U11	U22	U33	U12	U13	U23
F1	0.0593 (11)	0.0901 (16)	0.1083 (16)	−0.0182 (10)	0.0008 (10)	0.0475 (13)
F1'	0.0602 (14)	0.111 (2)	0.0770 (17)	−0.0076 (14)	−0.0306 (13)	0.0194 (16)
F2	0.0443 (5)	0.0795 (8)	0.0971 (9)	−0.0160 (5)	−0.0097 (5)	0.0008 (6)
O1	0.0498 (7)	0.0841 (10)	0.0580 (7)	−0.0110 (6)	−0.0045 (6)	0.0218 (7)
O2	0.0488 (6)	0.0697 (8)	0.0502 (7)	−0.0076 (6)	−0.0095 (5)	−0.0012 (6)
O3	0.0497 (7)	0.1028 (11)	0.0602 (8)	−0.0332 (7)	−0.0014 (6)	0.0012 (7)
C1	0.0492 (9)	0.0576 (11)	0.0454 (9)	−0.0017 (8)	−0.0057 (7)	0.0055 (8)
C2	0.0453 (9)	0.0650 (12)	0.0510 (10)	0.0007 (8)	−0.0140 (8)	0.0014 (8)
C3	0.0369 (8)	0.0538 (10)	0.0644 (10)	−0.0046 (7)	−0.0044 (7)	−0.0089 (8)
C4	0.0490 (9)	0.0506 (11)	0.0668 (11)	−0.0037 (8)	−0.0002 (8)	0.0092 (8)
C5	0.0431 (9)	0.0564 (11)	0.0550 (10)	0.0024 (8)	−0.0076 (7)	0.0088 (8)
C6	0.0403 (8)	0.0445 (9)	0.0436 (8)	0.0022 (7)	−0.0032 (6)	−0.0026 (7)
C7	0.0432 (8)	0.0498 (10)	0.0438 (9)	−0.0001 (7)	0.0007 (7)	−0.0001 (7)
C8	0.0420 (8)	0.0550 (10)	0.0534 (10)	−0.0056 (7)	−0.0052 (7)	0.0080 (8)
C9	0.0404 (8)	0.0498 (10)	0.0514 (9)	−0.0002 (7)	−0.0006 (7)	0.0047 (8)
C10	0.0381 (8)	0.0437 (9)	0.0498 (9)	−0.0031 (7)	−0.0014 (7)	0.0007 (7)
C11	0.0442 (9)	0.0694 (12)	0.0616 (11)	−0.0195 (8)	−0.0055 (8)	0.0140 (9)
C12	0.0544 (10)	0.0688 (12)	0.0515 (10)	−0.0157 (9)	−0.0053 (8)	0.0157 (8)
C13	0.0422 (8)	0.0449 (9)	0.0496 (9)	−0.0010 (7)	−0.0050 (7)	−0.0035 (7)
C14	0.0364 (8)	0.0472 (10)	0.0533 (9)	−0.0065 (7)	0.0005 (7)	−0.0070 (7)
C15	0.0430 (8)	0.0454 (9)	0.0465 (9)	−0.0033 (7)	0.0041 (7)	−0.0017 (7)
C16	0.0654 (11)	0.0901 (15)	0.0523 (11)	−0.0033 (10)	−0.0120 (9)	0.0085 (10)
C17	0.0639 (12)	0.0933 (16)	0.0735 (13)	−0.0337 (11)	0.0201 (10)	−0.0104 (11)

F1—C4	1.313 (2)	C7—H7	0.9300
F1'—C2	1.302 (2)	C8—C9	1.476 (2)
F2—C3	1.3468 (12)	C8—H8	0.9300
O1—C9	1.2220 (19)	C9—C10	1.484 (2)
O2—C13	1.3516 (17)	C10—C11	1.371 (2)
O2—C16	1.421 (2)	C10—C15	1.403 (2)
O3—C14	1.3662 (18)	C11—C12	1.383 (2)
O3—C17	1.405 (2)	C11—H11	0.9300
C1—C2	1.3784 (18)	C12—C13	1.374 (2)
C1—C6	1.391 (2)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.408 (2)
C2—C3	1.3650	C14—C15	1.366 (2)
C2—H2	0.9600	C15—H15	0.9300
C3—C4	1.3753	C16—H16A	0.9600
C4—C5	1.3703	C16—H16B	0.9600
C4—H4'	0.9600	C16—H16C	0.9600
C5—C6	1.3866 (18)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—C7	1.469 (2)	C17—H17C	0.9600
C7—C8	1.319 (2)
C13—O2—C16	118.12 (13)	C8—C9—C10	119.32 (14)
C14—O3—C17	118.42 (14)	C11—C10—C15	118.39 (14)
C2—C1—C6	120.61 (15)	C11—C10—C9	123.07 (14)
C2—C1—H1	119.7	C15—C10—C9	118.47 (14)
C6—C1—H1	119.7	C10—C11—C12	121.53 (15)
F1'—C2—C3	118.67 (13)	C10—C11—H11	119.2
F1'—C2—C1	121.57 (16)	C12—C11—H11	119.2
C3—C2—C1	119.62 (8)	C13—C12—C11	120.20 (16)
C3—C2—H2	120.2	C13—C12—H12	119.9
C1—C2—H2	120.2	C11—C12—H12	119.9
F2—C3—C2	120.03 (6)	O2—C13—C12	125.48 (15)
F2—C3—C4	119.45 (6)	O2—C13—C14	115.52 (13)
C2—C3—C4	120.5	C12—C13—C14	118.99 (14)
F1—C4—C5	121.27 (9)	O3—C14—C15	125.60 (15)
F1—C4—C3	118.29 (9)	O3—C14—C13	114.15 (13)
C5—C4—C3	120.3	C15—C14—C13	120.22 (13)
C5—C4—H4'	119.8	C14—C15—C10	120.68 (15)
C3—C4—H4'	119.8	C14—C15—H15	119.7
C4—C5—C6	120.17 (6)	C10—C15—H15	119.7
C4—C5—H5	119.9	O2—C16—H16A	109.5
C6—C5—H5	119.9	O2—C16—H16B	109.5
C5—C6—C1	118.75 (13)	H16A—C16—H16B	109.5
C5—C6—C7	122.34 (12)	O2—C16—H16C	109.5
C1—C6—C7	118.89 (14)	H16A—C16—H16C	109.5
C8—C7—C6	126.89 (15)	H16B—C16—H16C	109.5
C8—C7—H7	116.6	O3—C17—H17A	109.5
C6—C7—H7	116.6	O3—C17—H17B	109.5
C7—C8—C9	121.78 (15)	H17A—C17—H17B	109.5
C7—C8—H8	119.1	O3—C17—H17C	109.5
C9—C8—H8	119.1	H17A—C17—H17C	109.5
O1—C9—C8	120.35 (14)	H17B—C17—H17C	109.5
O1—C9—C10	120.29 (14)
C6—C1—C2—F1'	−175.4 (2)	O1—C9—C10—C11	171.47 (18)
C6—C1—C2—C3	0.14 (19)	C8—C9—C10—C11	−6.5 (3)
F1'—C2—C3—F2	−4.45 (17)	O1—C9—C10—C15	−5.4 (2)
C1—C2—C3—F2	179.90 (13)	C8—C9—C10—C15	176.53 (15)
F1'—C2—C3—C4	175.63 (17)	C15—C10—C11—C12	0.5 (3)
C1—C2—C3—C4	−0.03 (9)	C9—C10—C11—C12	−176.42 (17)
F2—C3—C4—F1	3.98 (15)	C10—C11—C12—C13	0.0 (3)
C2—C3—C4—F1	−176.10 (14)	C16—O2—C13—C12	−4.5 (3)
F2—C3—C4—C5	−179.96 (7)	C16—O2—C13—C14	174.74 (16)
C2—C3—C4—C5	0.0	C11—C12—C13—O2	178.70 (16)
F1—C4—C5—C6	175.92 (18)	C11—C12—C13—C14	−0.5 (3)
C3—C4—C5—C6	−0.02 (8)	C17—O3—C14—C15	5.4 (3)
C4—C5—C6—C1	0.13 (17)	C17—O3—C14—C13	−172.30 (16)
C4—C5—C6—C7	178.41 (10)	O2—C13—C14—O3	−0.9 (2)
C2—C1—C6—C5	−0.2 (2)	C12—C13—C14—O3	178.39 (16)
C2—C1—C6—C7	−178.53 (13)	O2—C13—C14—C15	−178.80 (14)
C5—C6—C7—C8	−2.0 (3)	C12—C13—C14—C15	0.5 (2)
C1—C6—C7—C8	176.24 (16)	O3—C14—C15—C10	−177.60 (16)
C6—C7—C8—C9	−177.52 (15)	C13—C14—C15—C10	0.0 (2)
C7—C8—C9—O1	−11.8 (3)	C11—C10—C15—C14	−0.5 (2)
C7—C8—C9—C10	166.18 (16)	C9—C10—C15—C14	176.55 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1i	0.93	2.44	3.321 (2)	159
C5—H5···O2ii	0.93	2.60	3.2769 (15)	130
C5—H5···O3ii	0.93	2.49	3.3950 (15)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.93	2.44	3.321 (2)	159
C5—H5⋯O2ii	0.93	2.60	3.2769 (15)	130
C5—H5⋯O3ii	0.93	2.49	3.3950 (15)	164

Symmetry codes: (i) ; (ii) .