(E)-3-(4-Chloro-phen-yl)-1-(4-fluoro-phenyl)-prop-2-en-1-one.

In the title compound, C(15)H(10)ClFO, the fluoro-substituted benzene ring forms a dihedral angle of 44.41 (6)° with the chloro-substituted benzene ring. The only significant directional bonds in the crystal are weak C-H⋯π inter-actions.

Related literature

For related structures and background to chalcone derivatives, see: Fun, Loh et al. (2011 ▶); Fun, Arshad et al. (2011a ▶,b ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H10ClFO

M = 260.68

Triclinic,

a = 5.8875 (3) Å

b = 7.4926 (3) Å

c = 13.6022 (6) Å

α = 80.351 (1)°

β = 85.483 (1)°

γ = 83.545 (1)°

V = 586.69 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 100 K

0.38 × 0.25 × 0.10 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.887, T max = 0.970

12071 measured reflections

3057 independent reflections

2785 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.07

3057 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004230/hb6622sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004230/hb6622Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004230/hb6622Isup3.cml

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

C15H10ClFO	Z = 2
Mr = 260.68	F(000) = 268
Triclinic, P1	Dx = 1.476 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8875 (3) Å	Cell parameters from 7331 reflections
b = 7.4926 (3) Å	θ = 3.0–32.5°
c = 13.6022 (6) Å	µ = 0.32 mm−1
α = 80.351 (1)°	T = 100 K
β = 85.483 (1)°	Block, colourless
γ = 83.545 (1)°	0.38 × 0.25 × 0.10 mm
V = 586.69 (5) Å3

Bruker APEX DUO CCD diffractometer	3057 independent reflections
Radiation source: fine-focus sealed tube	2785 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 29.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.887, Tmax = 0.970	k = −9→10
12071 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.040P)2 + 0.2844P] where P = (Fo2 + 2Fc2)/3
3057 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	1.24305 (5)	0.70656 (4)	0.56678 (2)	0.02277 (9)
F1	0.67229 (14)	−0.16353 (11)	1.43564 (6)	0.02659 (18)
O1	0.28078 (15)	0.20326 (13)	1.02611 (7)	0.02103 (19)
C1	0.75843 (19)	0.01108 (16)	1.17275 (9)	0.0167 (2)
H1A	0.8750	0.0160	1.1224	0.020*
C2	0.8030 (2)	−0.07852 (16)	1.26851 (9)	0.0181 (2)
H2A	0.9476	−0.1363	1.2827	0.022*
C3	0.6274 (2)	−0.07948 (16)	1.34189 (9)	0.0180 (2)
C4	0.4079 (2)	0.00187 (16)	1.32499 (9)	0.0187 (2)
H4A	0.2937	−0.0005	1.3764	0.022*
C5	0.36448 (19)	0.08690 (16)	1.22882 (9)	0.0166 (2)
H5A	0.2177	0.1402	1.2149	0.020*
C6	0.53854 (19)	0.09366 (15)	1.15221 (8)	0.0145 (2)
C7	0.4793 (2)	0.18765 (16)	1.05049 (9)	0.0159 (2)
C8	0.6648 (2)	0.26517 (16)	0.98177 (9)	0.0171 (2)
H8A	0.8077	0.2703	1.0053	0.021*
C9	0.62591 (19)	0.32760 (15)	0.88590 (9)	0.0159 (2)
H9A	0.4837	0.3114	0.8654	0.019*
C10	0.78251 (19)	0.41862 (15)	0.80970 (8)	0.0146 (2)
C11	0.72368 (19)	0.45188 (15)	0.70992 (9)	0.0157 (2)
H11A	0.5880	0.4140	0.6939	0.019*
C12	0.8636 (2)	0.54020 (16)	0.63434 (9)	0.0166 (2)
H12A	0.8234	0.5610	0.5683	0.020*
C13	1.0645 (2)	0.59650 (15)	0.65976 (8)	0.0163 (2)
C14	1.12740 (19)	0.56716 (15)	0.75820 (9)	0.0161 (2)
H14A	1.2621	0.6071	0.7738	0.019*
C15	0.98717 (19)	0.47788 (15)	0.83265 (8)	0.0158 (2)
H15A	1.0290	0.4570	0.8984	0.019*

	U11	U22	U33	U12	U13	U23
Cl1	0.02360 (16)	0.02747 (16)	0.01765 (15)	−0.01091 (11)	0.00178 (11)	−0.00064 (11)
F1	0.0263 (4)	0.0319 (4)	0.0177 (4)	−0.0017 (3)	−0.0043 (3)	0.0076 (3)
O1	0.0149 (4)	0.0287 (5)	0.0188 (4)	−0.0027 (3)	−0.0030 (3)	−0.0005 (3)
C1	0.0139 (5)	0.0187 (5)	0.0175 (5)	−0.0019 (4)	0.0003 (4)	−0.0034 (4)
C2	0.0144 (5)	0.0178 (5)	0.0216 (6)	0.0002 (4)	−0.0031 (4)	−0.0015 (4)
C3	0.0205 (5)	0.0171 (5)	0.0158 (5)	−0.0035 (4)	−0.0035 (4)	0.0014 (4)
C4	0.0168 (5)	0.0209 (5)	0.0173 (5)	−0.0031 (4)	0.0017 (4)	−0.0008 (4)
C5	0.0129 (5)	0.0175 (5)	0.0189 (5)	−0.0014 (4)	−0.0006 (4)	−0.0016 (4)
C6	0.0145 (5)	0.0145 (5)	0.0146 (5)	−0.0027 (4)	−0.0015 (4)	−0.0019 (4)
C7	0.0155 (5)	0.0166 (5)	0.0155 (5)	−0.0024 (4)	−0.0012 (4)	−0.0024 (4)
C8	0.0142 (5)	0.0197 (5)	0.0175 (5)	−0.0034 (4)	−0.0011 (4)	−0.0021 (4)
C9	0.0139 (5)	0.0158 (5)	0.0181 (5)	−0.0016 (4)	−0.0008 (4)	−0.0024 (4)
C10	0.0139 (5)	0.0141 (5)	0.0155 (5)	−0.0003 (4)	−0.0009 (4)	−0.0019 (4)
C11	0.0138 (5)	0.0166 (5)	0.0171 (5)	−0.0016 (4)	−0.0025 (4)	−0.0026 (4)
C12	0.0174 (5)	0.0181 (5)	0.0142 (5)	−0.0013 (4)	−0.0026 (4)	−0.0016 (4)
C13	0.0163 (5)	0.0158 (5)	0.0161 (5)	−0.0018 (4)	0.0014 (4)	−0.0014 (4)
C14	0.0136 (5)	0.0169 (5)	0.0183 (5)	−0.0021 (4)	−0.0019 (4)	−0.0038 (4)
C15	0.0156 (5)	0.0175 (5)	0.0143 (5)	−0.0002 (4)	−0.0024 (4)	−0.0023 (4)

Cl1—C13	1.7379 (12)	C8—C9	1.3380 (16)
F1—C3	1.3560 (13)	C8—H8A	0.9300
O1—C7	1.2279 (14)	C9—C10	1.4640 (15)
C1—C2	1.3919 (16)	C9—H9A	0.9300
C1—C6	1.3985 (15)	C10—C11	1.4020 (15)
C1—H1A	0.9300	C10—C15	1.4044 (16)
C2—C3	1.3790 (17)	C11—C12	1.3909 (16)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.3845 (17)	C12—C13	1.3862 (16)
C4—C5	1.3853 (16)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.3927 (16)
C5—C6	1.4016 (15)	C14—C15	1.3856 (16)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.4919 (15)	C15—H15A	0.9300
C7—C8	1.4844 (16)
C2—C1—C6	120.06 (10)	C7—C8—H8A	120.1
C2—C1—H1A	120.0	C8—C9—C10	127.19 (11)
C6—C1—H1A	120.0	C8—C9—H9A	116.4
C3—C2—C1	118.38 (11)	C10—C9—H9A	116.4
C3—C2—H2A	120.8	C11—C10—C15	118.49 (10)
C1—C2—H2A	120.8	C11—C10—C9	118.77 (10)
F1—C3—C2	118.32 (11)	C15—C10—C9	122.72 (10)
F1—C3—C4	118.26 (10)	C12—C11—C10	121.49 (10)
C2—C3—C4	123.42 (11)	C12—C11—H11A	119.3
C3—C4—C5	117.61 (11)	C10—C11—H11A	119.3
C3—C4—H4A	121.2	C13—C12—C11	118.42 (10)
C5—C4—H4A	121.2	C13—C12—H12A	120.8
C4—C5—C6	120.94 (11)	C11—C12—H12A	120.8
C4—C5—H5A	119.5	C12—C13—C14	121.65 (11)
C6—C5—H5A	119.5	C12—C13—Cl1	119.39 (9)
C1—C6—C5	119.56 (10)	C14—C13—Cl1	118.95 (9)
C1—C6—C7	122.44 (10)	C15—C14—C13	119.32 (10)
C5—C6—C7	118.00 (10)	C15—C14—H14A	120.3
O1—C7—C8	121.55 (10)	C13—C14—H14A	120.3
O1—C7—C6	120.21 (10)	C14—C15—C10	120.63 (10)
C8—C7—C6	118.22 (10)	C14—C15—H15A	119.7
C9—C8—C7	119.82 (10)	C10—C15—H15A	119.7
C9—C8—H8A	120.1
C6—C1—C2—C3	−1.50 (17)	C6—C7—C8—C9	170.70 (11)
C1—C2—C3—F1	−178.63 (10)	C7—C8—C9—C10	175.68 (11)
C1—C2—C3—C4	0.96 (18)	C8—C9—C10—C11	171.25 (11)
F1—C3—C4—C5	−179.88 (10)	C8—C9—C10—C15	−10.24 (19)
C2—C3—C4—C5	0.53 (18)	C15—C10—C11—C12	0.45 (17)
C3—C4—C5—C6	−1.49 (18)	C9—C10—C11—C12	179.03 (10)
C2—C1—C6—C5	0.58 (17)	C10—C11—C12—C13	−0.35 (17)
C2—C1—C6—C7	−178.48 (11)	C11—C12—C13—C14	−0.20 (17)
C4—C5—C6—C1	0.96 (17)	C11—C12—C13—Cl1	179.80 (9)
C4—C5—C6—C7	−179.94 (10)	C12—C13—C14—C15	0.65 (17)
C1—C6—C7—O1	155.13 (12)	Cl1—C13—C14—C15	−179.35 (9)
C5—C6—C7—O1	−23.93 (17)	C13—C14—C15—C10	−0.54 (17)
C1—C6—C7—C8	−26.56 (16)	C11—C10—C15—C14	0.00 (17)
C5—C6—C7—C8	154.38 (11)	C9—C10—C15—C14	−178.52 (10)
O1—C7—C8—C9	−11.02 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···Cg2i	0.93	2.85	3.4390 (13)	122
C5—H5A···Cg2ii	0.93	2.85	3.3989 (13)	119

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C15 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯Cg2i	0.93	2.85	3.4390 (13)	122
C5—H5A⋯Cg2ii	0.93	2.85	3.3989 (13)	119

Symmetry codes: (i) ; (ii) .