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

Fun, H.-K.; Chia, T.S.; Sapnakumari, M.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812004230

organic compounds

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Volume 68| Part 3| March 2012| Page o629

doi:10.1107/S1600536812004230

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

Hoong-Kun Fun,^a ^*‡ Tze Shyang Chia,^a M. Sapnakumari,^b B. Narayana ^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, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 31 January 2012; accepted 1 February 2012; online 10 February 2012)

In the title compound, C₁₅H₁₀ClFO, 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 interactions.

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_r = 260.68
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.086
S = 1.07
3057 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) -x+2, -y, -z+2; (ii) -x+1, -y+1, -z+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/S1600536812004230/hb6622sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812004230/hb6622Isup3.cml

checkCIF report

Comment top

In continuation of our work on the synthesis and structures of chalcone derivatives (Fun, Arshad et al., 2011a,b; Fun, Loh et al., 2011), the title compound was prepared and its crystal structure is reported.

The molecular structure of the title compound is shown in Fig. 1. The least-squares plane of the fluoro-substituted benzene ring (C1–C6) makes a dihedral angle of 44.41 (6)° with the least-squares plane of the chloro-substituted benzene ring (C10–C15). Bond lengths are comparable to those in related structures (Fun, Arshad et al., 2011a,b; Fun, Loh et al., 2011).

In the crystal structure, no significant intermolecular hydrogen bonds are observed. The crystal structure features were C—H···π interactions (Table 1), involving the centroid of C10–C15 benzene ring.

Related literature top

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 top

To a mixture of 4-fluoroacetophenone (1.38 g, 0.01 mol) and 4-chlorobenzaldehyde (1.41 g, 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 toluene as solvent by the slow evaporation method (m.p.: 405–407 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 with 50% probability displacement ellipsoids.

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

Crystal data top

C₁₅H₁₀ClFO	Z = 2
M_r = 260.68	F(000) = 268
Triclinic, P1	D_x = 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

Data collection top

Bruker APEX DUO CCD diffractometer	3057 independent reflections
Radiation source: fine-focus sealed tube	2785 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 29.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.887, T_max = 0.970	k = −9→10
12071 measured reflections	l = −18→18

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.040P)² + 0.2844P] where P = (F_o² + 2F_c²)/3
3057 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₀ClFO	γ = 83.545 (1)°
M_r = 260.68	V = 586.69 (5) Å³
Triclinic, P1	Z = 2
a = 5.8875 (3) Å	Mo Kα radiation
b = 7.4926 (3) Å	µ = 0.32 mm⁻¹
c = 13.6022 (6) Å	T = 100 K
α = 80.351 (1)°	0.38 × 0.25 × 0.10 mm
β = 85.483 (1)°

Data collection top

Bruker APEX DUO CCD diffractometer	3057 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2785 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.970	R_int = 0.021
12071 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.07	Δρ_max = 0.45 e Å⁻³
3057 reflections	Δρ_min = −0.25 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z+2; (ii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀ClFO
M_r	260.68
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.8875 (3), 7.4926 (3), 13.6022 (6)
α, β, γ (°)	80.351 (1), 85.483 (1), 83.545 (1)
V (Å³)	586.69 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.38 × 0.25 × 0.10

Data collection
Diffractometer	Bruker APEX DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.887, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	12071, 3057, 2785
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.086, 1.07
No. of reflections	3057
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.25

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

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z+2; (ii) −x+1, −y+1, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PFIZIK/811160. TSC thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant No. 1001/PSKBP/8630013. BN thanks UGC, New Delhi, Government of India, for the purchase of chemicals through the SAP-DRS-Phase 1 programme.

References

Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Arshad, S., Sarojini, B. K., Khaleel, V. M. & Narayana, B. (2011a). Acta Cryst. E67, o1248–o1249. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Arshad, S., Sarojini, B. K., Khaleel, V. M. & Narayana, B. (2011b). Acta Cryst. E67, o1372–o1373. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Loh, W.-S., Sarojini, B. K., Khaleel, V. M. & Narayana, B. (2011). Acta Cryst. E67, o1313–o1314. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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