(2E)-3-(2-Fluoro­phen­yl)-1-(4-fluoro­phen­yl)prop-2-en-1-one

Abstract

In the title compouund, C₁₅H₁₀F₂O, the mol­ecule exists in an E conformation with respect to the C=C bond [1.3382 (16) Å]. The dihedral angle between the fluoro-substituted benzene rings is 6.80 (6)° and the whole mol­ecule is roughly planar (r.m.s. deviation for the non-H atoms = 0.069 Å). In the crystal, mol­ecules are linked by C—H⋯F and C—H⋯O inter­actions into sheets lying parallel to the bc plane.

Related literature  

For details of the synthesis of chalcones, see: Fun et al. (2012 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental  

Crystal data  

• C₁₅H₁₀F₂O

• M _r = 244.23

• Monoclinic,

• a = 14.569 (2) Å

• b = 7.2737 (10) Å

• c = 11.3933 (15) Å

• β = 108.827 (3)°

• V = 1142.7 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 0.11 mm⁻¹

• T = 100 K

• 0.25 × 0.23 × 0.10 mm

Data collection  

• Bruker APEX DUO CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.973, T _max = 0.989

• 12454 measured reflections

• 3316 independent reflections

• 2525 reflections with I > 2σ(I)

• R _int = 0.031

Refinement  

• R[F ² > 2σ(F ²)] = 0.042

• wR(F ²) = 0.121

• S = 1.02

• 3316 reflections

• 163 parameters

• H-atom parameters constrained

• Δρ_max = 0.34 e Å⁻³

• Δρ_min = −0.27 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 ▶).

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536812034411/hb6921Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯F2i	0.95	2.47	3.4145 (16)	175
C14—H14A⋯F1ii	0.95	2.54	3.4816 (16)	174
C15—H15A⋯O1iii	0.95	2.55	3.4956 (15)	174

Symmetry codes: (i) ; (ii) ; (iii) .

supplementary crystallographic information

Comment

In continuation of our work on synthesis of chalcone derivatives (Fun et al., 2012), the title compound (I) has been prepared and its crystal structure is now reported.

In the title compouund (Fig. 1), the molecule exists in an E conformation with respect to C8═C9 [1.3382 (16) Å]. The dihedral angle between the fluoro-substituted (C1–C6 & C10–C15) benzene rings is 6.80 (6)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal structure (Fig. 2), the molecules are linked via C4—H4A···F2, C14—H14A···F1 and C15—H15A···O1 hydrogen bonds (Table 1) into two dimensional networks parallel to bc plane.

Experimental

To a mixture of 4-fluoroacetophenone (1.38 g, 0.01 mol) and 2-fluorobenzaldehyde (1.05 ml, 0.01 mol) in ethanol (100 ml), 15 ml of 10% sodium hydroxide solution was added and stirred at 0–5 °C for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Colourless blocks were grown from methanol solution by the slow evaporation method (M.P.: 351 K).

Refinement

All the H atoms were positioned geometrically and refined using a riding model with U_iso(H) = 1.2 U_eq(C) (C—H = 0.95 Å).

Figures

Fig. 1.

The molecular structure of the title compound, showing 50% probability displacement ellipsoids.

Fig. 2.

The crystal packing of the title compound, viewed along the b axis.

Crystal data

C15H10F2O	F(000) = 504
Mr = 244.23	Dx = 1.420 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3240 reflections
a = 14.569 (2) Å	θ = 3.0–30.0°
b = 7.2737 (10) Å	µ = 0.11 mm−1
c = 11.3933 (15) Å	T = 100 K
β = 108.827 (3)°	Block, colourless
V = 1142.7 (3) Å3	0.25 × 0.23 × 0.10 mm
Z = 4

Data collection

Bruker APEX DUO CCD diffractometer	3316 independent reflections
Radiation source: fine-focus sealed tube	2525 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 30.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→19
Tmin = 0.973, Tmax = 0.989	k = −8→10
12454 measured reflections	l = −14→16

Refinement

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0556P)2 + 0.4256P] where P = (Fo2 + 2Fc2)/3
3316 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.16014 (5)	0.57105 (12)	0.38021 (7)	0.0270 (2)
F2	0.88539 (6)	0.90022 (15)	0.48557 (7)	0.0357 (2)
O1	0.56195 (6)	0.67338 (14)	0.29627 (8)	0.0249 (2)
C1	0.40989 (8)	0.71839 (17)	0.49338 (11)	0.0190 (2)
H1A	0.4546	0.7712	0.5656	0.023*
C2	0.31519 (9)	0.68328 (18)	0.48962 (11)	0.0203 (2)
H2A	0.2945	0.7111	0.5586	0.024*
C3	0.25209 (8)	0.60721 (17)	0.38349 (11)	0.0195 (2)
C4	0.27869 (9)	0.56238 (18)	0.28129 (11)	0.0209 (3)
H4A	0.2334	0.5097	0.2096	0.025*
C5	0.37332 (9)	0.59650 (18)	0.28640 (11)	0.0193 (2)
H5A	0.3935	0.5653	0.2176	0.023*
C6	0.43978 (8)	0.67640 (16)	0.39157 (11)	0.0171 (2)
C7	0.54041 (8)	0.71165 (17)	0.38906 (11)	0.0181 (2)
C8	0.61241 (8)	0.79265 (18)	0.50023 (11)	0.0198 (2)
H8A	0.5931	0.8268	0.5693	0.024*
C9	0.70435 (8)	0.81809 (17)	0.50426 (11)	0.0189 (2)
H9A	0.7203	0.7847	0.4326	0.023*
C10	0.78236 (8)	0.89267 (17)	0.60915 (11)	0.0183 (2)
C11	0.87245 (9)	0.93383 (19)	0.59684 (11)	0.0222 (3)
C12	0.94940 (9)	1.0061 (2)	0.69058 (13)	0.0264 (3)
H12A	1.0091	1.0334	0.6773	0.032*
C13	0.93744 (9)	1.0379 (2)	0.80465 (12)	0.0256 (3)
H13A	0.9893	1.0873	0.8710	0.031*
C14	0.84936 (9)	0.9974 (2)	0.82199 (12)	0.0252 (3)
H14A	0.8416	1.0181	0.9006	0.030*
C15	0.77291 (9)	0.92723 (18)	0.72577 (12)	0.0215 (3)
H15A	0.7130	0.9021	0.7390	0.026*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
F1	0.0162 (3)	0.0386 (5)	0.0260 (4)	−0.0048 (3)	0.0066 (3)	−0.0005 (3)
F2	0.0216 (4)	0.0672 (7)	0.0203 (4)	−0.0037 (4)	0.0097 (3)	−0.0020 (4)
O1	0.0216 (4)	0.0347 (5)	0.0197 (4)	−0.0006 (4)	0.0083 (3)	−0.0016 (4)
C1	0.0180 (5)	0.0196 (6)	0.0180 (5)	−0.0003 (4)	0.0037 (4)	−0.0008 (5)
C2	0.0196 (5)	0.0232 (6)	0.0184 (6)	0.0001 (5)	0.0068 (4)	−0.0013 (5)
C3	0.0156 (5)	0.0208 (6)	0.0215 (6)	−0.0006 (4)	0.0052 (4)	0.0033 (5)
C4	0.0199 (5)	0.0233 (6)	0.0166 (5)	−0.0022 (5)	0.0019 (4)	0.0014 (5)
C5	0.0209 (5)	0.0213 (6)	0.0151 (5)	0.0001 (4)	0.0048 (4)	0.0009 (4)
C6	0.0167 (5)	0.0164 (5)	0.0173 (5)	0.0015 (4)	0.0042 (4)	0.0018 (4)
C7	0.0180 (5)	0.0181 (6)	0.0176 (5)	0.0015 (4)	0.0050 (4)	0.0028 (4)
C8	0.0192 (5)	0.0220 (6)	0.0180 (5)	−0.0003 (4)	0.0056 (4)	−0.0003 (5)
C9	0.0185 (5)	0.0213 (6)	0.0166 (5)	0.0012 (4)	0.0052 (4)	0.0022 (4)
C10	0.0164 (5)	0.0195 (6)	0.0185 (5)	0.0018 (4)	0.0048 (4)	0.0037 (5)
C11	0.0184 (5)	0.0316 (7)	0.0172 (5)	0.0021 (5)	0.0067 (4)	0.0032 (5)
C12	0.0152 (5)	0.0373 (8)	0.0255 (6)	−0.0016 (5)	0.0047 (5)	0.0030 (6)
C13	0.0193 (6)	0.0308 (7)	0.0230 (6)	−0.0013 (5)	0.0019 (5)	−0.0008 (5)
C14	0.0230 (6)	0.0318 (7)	0.0200 (6)	0.0007 (5)	0.0061 (5)	−0.0025 (5)
C15	0.0179 (5)	0.0260 (6)	0.0210 (6)	−0.0003 (5)	0.0068 (4)	0.0008 (5)

Geometric parameters (Å, º)

F1—C3	1.3539 (13)	C8—C9	1.3382 (16)
F2—C11	1.3627 (14)	C8—H8A	0.9500
O1—C7	1.2279 (15)	C9—C10	1.4621 (17)
C1—C2	1.3901 (16)	C9—H9A	0.9500
C1—C6	1.3980 (16)	C10—C11	1.3966 (16)
C1—H1A	0.9500	C10—C15	1.4021 (17)
C2—C3	1.3769 (17)	C11—C12	1.3788 (18)
C2—H2A	0.9500	C12—C13	1.3852 (19)
C3—C4	1.3797 (17)	C12—H12A	0.9500
C4—C5	1.3834 (17)	C13—C14	1.3915 (18)
C4—H4A	0.9500	C13—H13A	0.9500
C5—C6	1.4007 (16)	C14—C15	1.3837 (18)
C5—H5A	0.9500	C14—H14A	0.9500
C6—C7	1.4977 (16)	C15—H15A	0.9500
C7—C8	1.4813 (17)
C2—C1—C6	120.40 (11)	C7—C8—H8A	119.7
C2—C1—H1A	119.8	C8—C9—C10	125.79 (11)
C6—C1—H1A	119.8	C8—C9—H9A	117.1
C3—C2—C1	118.40 (11)	C10—C9—H9A	117.1
C3—C2—H2A	120.8	C11—C10—C15	116.08 (11)
C1—C2—H2A	120.8	C11—C10—C9	120.35 (11)
F1—C3—C2	118.46 (11)	C15—C10—C9	123.57 (10)
F1—C3—C4	118.40 (11)	F2—C11—C12	117.84 (11)
C2—C3—C4	123.12 (11)	F2—C11—C10	118.14 (11)
C3—C4—C5	118.01 (11)	C12—C11—C10	124.02 (11)
C3—C4—H4A	121.0	C11—C12—C13	118.25 (11)
C5—C4—H4A	121.0	C11—C12—H12A	120.9
C4—C5—C6	120.98 (11)	C13—C12—H12A	120.9
C4—C5—H5A	119.5	C12—C13—C14	119.92 (12)
C6—C5—H5A	119.5	C12—C13—H13A	120.0
C1—C6—C5	119.08 (11)	C14—C13—H13A	120.0
C1—C6—C7	123.19 (10)	C15—C14—C13	120.60 (12)
C5—C6—C7	117.73 (10)	C15—C14—H14A	119.7
O1—C7—C8	121.28 (11)	C13—C14—H14A	119.7
O1—C7—C6	120.09 (11)	C14—C15—C10	121.11 (11)
C8—C7—C6	118.63 (10)	C14—C15—H15A	119.4
C9—C8—C7	120.60 (11)	C10—C15—H15A	119.4
C9—C8—H8A	119.7
C6—C1—C2—C3	−0.23 (19)	C6—C7—C8—C9	176.72 (11)
C1—C2—C3—F1	179.28 (11)	C7—C8—C9—C10	−178.59 (11)
C1—C2—C3—C4	0.7 (2)	C8—C9—C10—C11	−172.08 (13)
F1—C3—C4—C5	−178.75 (11)	C8—C9—C10—C15	7.9 (2)
C2—C3—C4—C5	−0.2 (2)	C15—C10—C11—F2	179.16 (11)
C3—C4—C5—C6	−0.83 (19)	C9—C10—C11—F2	−0.85 (19)
C2—C1—C6—C5	−0.76 (18)	C15—C10—C11—C12	−0.7 (2)
C2—C1—C6—C7	179.61 (11)	C9—C10—C11—C12	179.33 (13)
C4—C5—C6—C1	1.31 (18)	F2—C11—C12—C13	−178.95 (12)
C4—C5—C6—C7	−179.04 (11)	C10—C11—C12—C13	0.9 (2)
C1—C6—C7—O1	−179.26 (12)	C11—C12—C13—C14	−0.2 (2)
C5—C6—C7—O1	1.10 (17)	C12—C13—C14—C15	−0.7 (2)
C1—C6—C7—C8	0.84 (18)	C13—C14—C15—C10	0.9 (2)
C5—C6—C7—C8	−178.80 (11)	C11—C10—C15—C14	−0.25 (19)
O1—C7—C8—C9	−3.18 (19)	C9—C10—C15—C14	179.76 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···F2i	0.95	2.47	3.4145 (16)	175
C14—H14A···F1ii	0.95	2.54	3.4816 (16)	174
C15—H15A···O1iii	0.95	2.55	3.4956 (15)	174

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x, −y+3/2, z+1/2.