4-[2-(4-Fluoro­phen­yl)furan-3-yl]pyridine

Abu Thaher, B.; Koch, P.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536809003651

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o458

doi:10.1107/S1600536809003651

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4-[2-(4-Fluorophenyl)furan-3-yl]pyridine

Bassam Abu Thaher,^a Pierre Koch,^b Dieter Schollmeyer ^c and Stefan Laufer ^b ^*

^aFaculty of Science, Chemistry Department, Islamic University of Gaza, Gaza Strip, Palestinian Territories, ^bInstitute of Pharmacy, Department of Pharmaceutical and Medicinal Chemistry, Eberhard-Karls-University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and ^cDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 23 January 2009; accepted 29 January 2009; online 4 February 2009)

In the crystal structure of the title compound, C₁₅H₁₀FNO, the furan ring makes dihedral angles of 40.04 (11) and 25.71 (11)° with the pyridine and 4-fluorophenyl rings, respectively. The pyridine ring makes a dihedral angle of 49.51 (10)° with the 4-fluorophenyl ring. Non-conventional C—H⋯F and C—H⋯N hydrogen bonds are effective in the stabilization of the crystal structure.

Related literature

For the biological activities of related compounds, see: Wilkerson et al. (1985 ); Myers et al. (1985 ).

Experimental

Crystal data

C₁₅H₁₀FNO
M_r = 239.24
Monoclinic, P 2₁ /c
a = 13.343 (9) Å
b = 10.550 (3) Å
c = 8.178 (5) Å
β = 94.44 (3)°
V = 1147.7 (11) Å³
Z = 4
Cu Kα radiation
μ = 0.81 mm⁻¹
T = 193 (2) K
0.26 × 0.19 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2172 measured reflections
2172 independent reflections
1806 reflections with I > 2σ(I)
3 standard reflectionsfrequency: 60 min intensity decay: 2%

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.151
S = 1.07
2172 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯F1ⁱ	0.95	2.32	3.006 (3)	128
C8—H8⋯N15ⁱⁱ	0.95	2.60	3.483 (3)	155
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003651/bt2859sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003651/bt2859Isup2.hkl

checkCIF report

Comment top

Diarylfuran carbinols and methanamines (Wilkerson et al. 1985) and diaryl-thio-substituted furans (Myers et al. 1985) have been considered to be potential anti-inflammatory or analgetic agents.

The analysis of the crystal structure of the title compound is shown in Fig. 1. The furan ring makes dihedral angles of 40.04 (11)° and 25.71 (11)° to the pyridine ring and the 4-fluorophenyl ring, respectively. The pyridine ring makes a dihedral angle of 49.51 (10)° to the 4-fluorophenyl ring. Non-conventional C—H···X H-bonds seem to be effective in stabilization of the crystal structure. By intermolecular hydrogen bonds C5—H5···F1 (2.32 Å) and C8—H8···N15 (2.60 Å) a two-dimensional network parallel to the ab plane (Fig. 2) is formed.

Related literature top

For the biological activities of related compounds, see: Wilkerson et al. (1985); Myers et al. (1985).

Experimental top

4-(4-Fluorophenyl)-4-oxo-3-(pyridin-4-yl)butanal (2.0 g) was treated with glacial acetic acid (10 ml), conc. HCl (30 ml) and then heated to reflux temperature for 4 h. The reaction mixture was cooled to r.t. and put into ice. A solution of K₂CO₃ was added until it became basic. The aqueous phase was extracted four times with ethyl acetate and the combined organic layers were dried over Na₂SO₄ and filtered. The remaining solution was concentrated in vacuo and then purified by flash chromatography (SiO₂, petroleum ether/ethylacetate 2:1 to 1:1) to give compound I (1.15 g) as a pale yellow solid. For X-ray suitable crystals of compound I were obtained by slow evaporation at 298 K of a solution of n-hexane–ethyl acetate–diethyl ether.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. View of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are depicted as circles of arbitrary size.
	Fig. 2. Partial crystal packing diagram of the title compound. The hydrogen bonds are shown with dashed lines. View along the c axis.

4-[2-(4-Fluorophenyl)furan-3-yl]pyridine top

Crystal data top

C₁₅H₁₀FNO	F(000) = 496
M_r = 239.24	D_x = 1.385 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 13.343 (9) Å	θ = 35–47°
b = 10.550 (3) Å	µ = 0.81 mm⁻¹
c = 8.178 (5) Å	T = 193 K
β = 94.44 (3)°	Plate, colourless
V = 1147.7 (11) Å³	0.26 × 0.19 × 0.12 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.000
Radiation source: rotating anode	θ_max = 70.1°, θ_min = 3.3°
Graphite monochromator	h = 0→16
ω/2θ scans	k = 0→12
2172 measured reflections	l = −9→9
2172 independent reflections	3 standard reflections every 60 min
1806 reflections with I > 2σ(I)	intensity decay: 2%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.151	w = 1/[σ²(F_o²) + (0.084P)² + 0.3989P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2172 reflections	Δρ_max = 0.23 e Å⁻³
164 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (6)

Crystal data top

C₁₅H₁₀FNO	V = 1147.7 (11) Å³
M_r = 239.24	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 13.343 (9) Å	µ = 0.81 mm⁻¹
b = 10.550 (3) Å	T = 193 K
c = 8.178 (5) Å	0.26 × 0.19 × 0.12 mm
β = 94.44 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.000
2172 measured reflections	3 standard reflections every 60 min
2172 independent reflections	intensity decay: 2%
1806 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.07	Δρ_max = 0.23 e Å⁻³
2172 reflections	Δρ_min = −0.31 e Å⁻³
164 parameters

Special details top

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	0.12844 (11)	0.65865 (12)	0.4490 (2)	0.0657 (5)
O1	0.10747 (10)	0.06648 (13)	0.45018 (19)	0.0394 (4)
C2	0.19141 (14)	0.13786 (18)	0.4958 (2)	0.0324 (4)
C3	0.26801 (14)	0.05896 (18)	0.5490 (2)	0.0338 (5)
C4	0.22829 (15)	−0.06710 (19)	0.5367 (3)	0.0403 (5)
H4	0.2633	−0.1432	0.5656	0.048*
C5	0.13306 (16)	−0.0573 (2)	0.4771 (3)	0.0438 (5)
H5	0.0889	−0.1270	0.4561	0.053*
C6	0.17617 (13)	0.27453 (18)	0.4833 (2)	0.0315 (4)
C7	0.23331 (14)	0.35897 (19)	0.5837 (2)	0.0353 (5)
H7	0.2837	0.3267	0.6610	0.042*
C8	0.21809 (15)	0.4885 (2)	0.5730 (3)	0.0409 (5)
H8	0.2577	0.5455	0.6408	0.049*
C9	0.14411 (17)	0.53215 (19)	0.4616 (3)	0.0422 (5)
C10	0.08431 (16)	0.4532 (2)	0.3621 (3)	0.0421 (5)
H10	0.0329	0.4868	0.2876	0.051*
C11	0.10057 (15)	0.32439 (19)	0.3728 (3)	0.0364 (5)
H11	0.0601	0.2686	0.3046	0.044*
C12	0.37309 (14)	0.08896 (18)	0.6061 (2)	0.0323 (4)
C13	0.42007 (15)	0.0206 (2)	0.7362 (3)	0.0395 (5)
H13	0.3841	−0.0426	0.7902	0.047*
C14	0.51936 (16)	0.0457 (2)	0.7858 (3)	0.0425 (5)
H14	0.5500	−0.0029	0.8739	0.051*
N15	0.57492 (13)	0.13313 (18)	0.7186 (2)	0.0411 (5)
C16	0.52945 (15)	0.1975 (2)	0.5926 (3)	0.0389 (5)
H16	0.5676	0.2595	0.5405	0.047*
C17	0.43063 (15)	0.17936 (19)	0.5335 (3)	0.0356 (5)
H17	0.4024	0.2284	0.4439	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0692 (10)	0.0266 (7)	0.0986 (13)	0.0065 (6)	−0.0102 (8)	0.0003 (7)
O1	0.0293 (7)	0.0296 (7)	0.0575 (9)	−0.0026 (5)	−0.0079 (6)	−0.0016 (6)
C2	0.0274 (9)	0.0303 (10)	0.0383 (11)	−0.0035 (7)	−0.0038 (7)	−0.0019 (8)
C3	0.0310 (10)	0.0287 (10)	0.0406 (11)	0.0007 (8)	−0.0030 (8)	−0.0003 (8)
C4	0.0357 (11)	0.0289 (10)	0.0554 (13)	0.0023 (8)	−0.0017 (9)	0.0011 (9)
C5	0.0375 (11)	0.0253 (10)	0.0679 (15)	−0.0024 (8)	−0.0004 (10)	−0.0030 (9)
C6	0.0277 (9)	0.0306 (10)	0.0355 (10)	0.0014 (7)	−0.0019 (7)	−0.0001 (8)
C7	0.0308 (10)	0.0344 (11)	0.0392 (11)	0.0012 (8)	−0.0072 (8)	−0.0023 (8)
C8	0.0348 (11)	0.0337 (11)	0.0532 (13)	−0.0034 (8)	−0.0034 (9)	−0.0081 (9)
C9	0.0418 (12)	0.0264 (10)	0.0581 (14)	0.0035 (8)	0.0018 (9)	0.0009 (9)
C10	0.0396 (11)	0.0383 (12)	0.0467 (12)	0.0074 (9)	−0.0085 (9)	0.0033 (9)
C11	0.0327 (10)	0.0341 (10)	0.0410 (11)	0.0004 (8)	−0.0073 (8)	−0.0023 (8)
C12	0.0296 (10)	0.0293 (10)	0.0371 (10)	0.0037 (7)	−0.0035 (7)	−0.0040 (8)
C13	0.0373 (11)	0.0366 (11)	0.0438 (12)	0.0038 (8)	−0.0023 (9)	0.0042 (9)
C14	0.0389 (12)	0.0474 (12)	0.0396 (11)	0.0108 (9)	−0.0073 (9)	0.0016 (9)
N15	0.0345 (9)	0.0451 (11)	0.0420 (10)	0.0036 (7)	−0.0070 (7)	−0.0049 (8)
C16	0.0335 (10)	0.0380 (11)	0.0444 (11)	−0.0027 (8)	−0.0023 (8)	−0.0028 (9)
C17	0.0334 (10)	0.0341 (10)	0.0379 (10)	0.0011 (8)	−0.0071 (8)	0.0017 (8)

Geometric parameters (Å, º) top

F1—C9	1.354 (2)	C8—H8	0.9500
O1—C5	1.363 (2)	C9—C10	1.375 (3)
O1—C2	1.377 (2)	C10—C11	1.378 (3)
C2—C3	1.363 (3)	C10—H10	0.9500
C2—C6	1.459 (3)	C11—H11	0.9500
C3—C4	1.432 (3)	C12—C17	1.387 (3)
C3—C12	1.478 (3)	C12—C13	1.393 (3)
C4—C5	1.329 (3)	C13—C14	1.381 (3)
C4—H4	0.9500	C13—H13	0.9500
C5—H5	0.9500	C14—N15	1.329 (3)
C6—C7	1.397 (3)	C14—H14	0.9500
C6—C11	1.403 (3)	N15—C16	1.339 (3)
C7—C8	1.384 (3)	C16—C17	1.382 (3)
C7—H7	0.9500	C16—H16	0.9500
C8—C9	1.370 (3)	C17—H17	0.9500

C5—O1—C2	106.97 (16)	C8—C9—C10	123.0 (2)
C3—C2—O1	109.06 (17)	C9—C10—C11	118.58 (19)
C3—C2—C6	136.31 (18)	C9—C10—H10	120.7
O1—C2—C6	114.55 (16)	C11—C10—H10	120.7
C2—C3—C4	106.28 (17)	C10—C11—C6	120.82 (19)
C2—C3—C12	129.79 (18)	C10—C11—H11	119.6
C4—C3—C12	123.92 (18)	C6—C11—H11	119.6
C5—C4—C3	106.96 (18)	C17—C12—C13	116.85 (18)
C5—C4—H4	126.5	C17—C12—C3	123.72 (18)
C3—C4—H4	126.5	C13—C12—C3	119.38 (18)
C4—C5—O1	110.72 (18)	C14—C13—C12	119.4 (2)
C4—C5—H5	124.6	C14—C13—H13	120.3
O1—C5—H5	124.6	C12—C13—H13	120.3
C7—C6—C11	118.14 (18)	N15—C14—C13	124.34 (19)
C7—C6—C2	121.48 (17)	N15—C14—H14	117.8
C11—C6—C2	120.34 (17)	C13—C14—H14	117.8
C8—C7—C6	121.47 (18)	C14—N15—C16	115.86 (18)
C8—C7—H7	119.3	N15—C16—C17	124.2 (2)
C6—C7—H7	119.3	N15—C16—H16	117.9
C9—C8—C7	117.94 (19)	C17—C16—H16	117.9
C9—C8—H8	121.0	C16—C17—C12	119.35 (19)
C7—C8—H8	121.0	C16—C17—H17	120.3
F1—C9—C8	118.7 (2)	C12—C17—H17	120.3
F1—C9—C10	118.2 (2)

C5—O1—C2—C3	0.5 (2)	C7—C8—C9—C10	0.7 (4)
C5—O1—C2—C6	−176.93 (18)	F1—C9—C10—C11	179.2 (2)
O1—C2—C3—C4	−0.6 (2)	C8—C9—C10—C11	−1.2 (4)
C6—C2—C3—C4	176.0 (2)	C9—C10—C11—C6	0.3 (3)
O1—C2—C3—C12	178.1 (2)	C7—C6—C11—C10	1.0 (3)
C6—C2—C3—C12	−5.3 (4)	C2—C6—C11—C10	178.8 (2)
C2—C3—C4—C5	0.5 (3)	C2—C3—C12—C17	−40.6 (3)
C12—C3—C4—C5	−178.3 (2)	C4—C3—C12—C17	138.0 (2)
C3—C4—C5—O1	−0.3 (3)	C2—C3—C12—C13	142.0 (2)
C2—O1—C5—C4	−0.1 (3)	C4—C3—C12—C13	−39.4 (3)
C3—C2—C6—C7	−24.2 (4)	C17—C12—C13—C14	0.1 (3)
O1—C2—C6—C7	152.23 (18)	C3—C12—C13—C14	177.75 (19)
C3—C2—C6—C11	158.1 (2)	C12—C13—C14—N15	0.8 (3)
O1—C2—C6—C11	−25.5 (3)	C13—C14—N15—C16	−1.4 (3)
C11—C6—C7—C8	−1.5 (3)	C14—N15—C16—C17	1.2 (3)
C2—C6—C7—C8	−179.28 (19)	N15—C16—C17—C12	−0.4 (3)
C6—C7—C8—C9	0.7 (3)	C13—C12—C17—C16	−0.3 (3)
C7—C8—C9—F1	−179.7 (2)	C3—C12—C17—C16	−177.80 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F1ⁱ	0.95	2.32	3.006 (3)	128
C8—H8···N15ⁱⁱ	0.95	2.60	3.483 (3)	155

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀FNO
M_r	239.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	13.343 (9), 10.550 (3), 8.178 (5)
β (°)	94.44 (3)
V (Å³)	1147.7 (11)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.26 × 0.19 × 0.12

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2172, 2172, 1806
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.151, 1.07
No. of reflections	2172
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.31

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CORINC (Dräger & Gattow, 1971), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F1ⁱ	0.95	2.32	3.006 (3)	128
C8—H8···N15ⁱⁱ	0.95	2.60	3.483 (3)	155

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

Acknowledgements

The authors thank the Alexander von Humbolt Foundation (AvH) for funding.

References

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