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

Fun, H.-K.; Farhadikoutenaei, A.; Narayana, B.; Nayak, P.S.; Sarojini, B.K.

doi:10.1107/S1600536812034411

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2658

doi:10.1107/S1600536812034411

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

Hoong-Kun Fun,^a ^*‡ Abbas Farhadikoutenaei,^a B. Narayana,^b Prakash S. Nayak ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Montepadavu, PO, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 30 July 2012; accepted 2 August 2012; online 8 August 2012)

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, P 2₁ /c
a = 14.569 (2) Å
b = 7.2737 (10) Å
c = 11.3933 (15) Å
β = 108.827 (3)°
V = 1142.7 (3) Å³
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[F² > 2σ(F²)] = 0.042
wR(F²) = 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

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034411/hb6921sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034411/hb6921Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034411/hb6921Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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).

Computing details top

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

Figures top

	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.

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

Crystal data top

C₁₅H₁₀F₂O	F(000) = 504
M_r = 244.23	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0556P)² + 0.4256P] where P = (F_o² + 2F_c²)/3
3316 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₅H₁₀F₂O	V = 1142.7 (3) Å³
M_r = 244.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.569 (2) Å	µ = 0.11 mm⁻¹
b = 7.2737 (10) Å	T = 100 K
c = 11.3933 (15) Å	0.25 × 0.23 × 0.10 mm
β = 108.827 (3)°

Data collection top

Bruker APEX DUO CCD diffractometer	3316 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2525 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.989	R_int = 0.031
12454 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	Δρ_max = 0.34 e Å⁻³
3316 reflections	Δρ_min = −0.27 e Å⁻³
163 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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) top

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) top

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.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀F₂O
M_r	244.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.569 (2), 7.2737 (10), 11.3933 (15)
β (°)	108.827 (3)
V (Å³)	1142.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.23 × 0.10

Data collection
Diffractometer	Bruker APEX DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.973, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	12454, 3316, 2525
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.121, 1.02
No. of reflections	3316
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.27

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and AF thank Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PFIZIK/811160. BN thanks UGC, New Delhi, and Government of India for the purchase of chemicals through the SAP-DRS-Phase 1 programme.

References

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Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
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