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Acta Cryst. (2009). E65, o458    [ doi:10.1107/S1600536809003651 ]

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

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

Abstract top

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.

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.

Refinement top

H atoms attached to carbons were placed at calculated positions with C—H = 0.95 Å. They were refined in the riding-model approximation with isotropic displacement parameters set to 1.2 times of the Ueq of the parent atom.

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
[Figure 1] 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.
[Figure 2] 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
C15H10FNOF(000) = 496
Mr = 239.24Dx = 1.385 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 13.343 (9) Åθ = 35–47°
b = 10.550 (3) ŵ = 0.81 mm−1
c = 8.178 (5) ÅT = 193 K
β = 94.44 (3)°Plate, colourless
V = 1147.7 (11) Å30.26 × 0.19 × 0.12 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.0000
Radiation source: rotating anodeθmax = 70.1°, θmin = 3.3°
graphiteh = 0→16
ω/2θ scansk = 0→12
2172 measured reflectionsl = −9→9
2172 independent reflections3 standard reflections every 60 min
1806 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.084P)2 + 0.3989P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2172 reflectionsΔρmax = 0.23 e Å−3
164 parametersΔρmin = −0.31 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (6)
Crystal data top
C15H10FNOV = 1147.7 (11) Å3
Mr = 239.24Z = 4
Monoclinic, P21/cCu Kα radiation
a = 13.343 (9) ŵ = 0.81 mm−1
b = 10.550 (3) ÅT = 193 K
c = 8.178 (5) Å0.26 × 0.19 × 0.12 mm
β = 94.44 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.0000
2172 measured reflectionsθmax = 70.1°
2172 independent reflections3 standard reflections every 60 min
1806 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.151Δρmax = 0.23 e Å−3
S = 1.07Δρmin = −0.31 e Å−3
2172 reflectionsAbsolute structure: ?
164 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
F10.12844 (11)0.65865 (12)0.4490 (2)0.0657 (5)
O10.10747 (10)0.06648 (13)0.45018 (19)0.0394 (4)
C20.19141 (14)0.13786 (18)0.4958 (2)0.0324 (4)
C30.26801 (14)0.05896 (18)0.5490 (2)0.0338 (5)
C40.22829 (15)−0.06710 (19)0.5367 (3)0.0403 (5)
H40.2633−0.14320.56560.048*
C50.13306 (16)−0.0573 (2)0.4771 (3)0.0438 (5)
H50.0889−0.12700.45610.053*
C60.17617 (13)0.27453 (18)0.4833 (2)0.0315 (4)
C70.23331 (14)0.35897 (19)0.5837 (2)0.0353 (5)
H70.28370.32670.66100.042*
C80.21809 (15)0.4885 (2)0.5730 (3)0.0409 (5)
H80.25770.54550.64080.049*
C90.14411 (17)0.53215 (19)0.4616 (3)0.0422 (5)
C100.08431 (16)0.4532 (2)0.3621 (3)0.0421 (5)
H100.03290.48680.28760.051*
C110.10057 (15)0.32439 (19)0.3728 (3)0.0364 (5)
H110.06010.26860.30460.044*
C120.37309 (14)0.08896 (18)0.6061 (2)0.0323 (4)
C130.42007 (15)0.0206 (2)0.7362 (3)0.0395 (5)
H130.3841−0.04260.79020.047*
C140.51936 (16)0.0457 (2)0.7858 (3)0.0425 (5)
H140.5500−0.00290.87390.051*
N150.57492 (13)0.13313 (18)0.7186 (2)0.0411 (5)
C160.52945 (15)0.1975 (2)0.5926 (3)0.0389 (5)
H160.56760.25950.54050.047*
C170.43063 (15)0.17936 (19)0.5335 (3)0.0356 (5)
H170.40240.22840.44390.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0692 (10)0.0266 (7)0.0986 (13)0.0065 (6)−0.0102 (8)0.0003 (7)
O10.0293 (7)0.0296 (7)0.0575 (9)−0.0026 (5)−0.0079 (6)−0.0016 (6)
C20.0274 (9)0.0303 (10)0.0383 (11)−0.0035 (7)−0.0038 (7)−0.0019 (8)
C30.0310 (10)0.0287 (10)0.0406 (11)0.0007 (8)−0.0030 (8)−0.0003 (8)
C40.0357 (11)0.0289 (10)0.0554 (13)0.0023 (8)−0.0017 (9)0.0011 (9)
C50.0375 (11)0.0253 (10)0.0679 (15)−0.0024 (8)−0.0004 (10)−0.0030 (9)
C60.0277 (9)0.0306 (10)0.0355 (10)0.0014 (7)−0.0019 (7)−0.0001 (8)
C70.0308 (10)0.0344 (11)0.0392 (11)0.0012 (8)−0.0072 (8)−0.0023 (8)
C80.0348 (11)0.0337 (11)0.0532 (13)−0.0034 (8)−0.0034 (9)−0.0081 (9)
C90.0418 (12)0.0264 (10)0.0581 (14)0.0035 (8)0.0018 (9)0.0009 (9)
C100.0396 (11)0.0383 (12)0.0467 (12)0.0074 (9)−0.0085 (9)0.0033 (9)
C110.0327 (10)0.0341 (10)0.0410 (11)0.0004 (8)−0.0073 (8)−0.0023 (8)
C120.0296 (10)0.0293 (10)0.0371 (10)0.0037 (7)−0.0035 (7)−0.0040 (8)
C130.0373 (11)0.0366 (11)0.0438 (12)0.0038 (8)−0.0023 (9)0.0042 (9)
C140.0389 (12)0.0474 (12)0.0396 (11)0.0108 (9)−0.0073 (9)0.0016 (9)
N150.0345 (9)0.0451 (11)0.0420 (10)0.0036 (7)−0.0070 (7)−0.0049 (8)
C160.0335 (10)0.0380 (11)0.0444 (11)−0.0027 (8)−0.0023 (8)−0.0028 (9)
C170.0334 (10)0.0341 (10)0.0379 (10)0.0011 (8)−0.0071 (8)0.0017 (8)
Geometric parameters (Å, °) top
F1—C91.354 (2)C8—H80.9500
O1—C51.363 (2)C9—C101.375 (3)
O1—C21.377 (2)C10—C111.378 (3)
C2—C31.363 (3)C10—H100.9500
C2—C61.459 (3)C11—H110.9500
C3—C41.432 (3)C12—C171.387 (3)
C3—C121.478 (3)C12—C131.393 (3)
C4—C51.329 (3)C13—C141.381 (3)
C4—H40.9500C13—H130.9500
C5—H50.9500C14—N151.329 (3)
C6—C71.397 (3)C14—H140.9500
C6—C111.403 (3)N15—C161.339 (3)
C7—C81.384 (3)C16—C171.382 (3)
C7—H70.9500C16—H160.9500
C8—C91.370 (3)C17—H170.9500
C5—O1—C2106.97 (16)C8—C9—C10123.0 (2)
C3—C2—O1109.06 (17)C9—C10—C11118.58 (19)
C3—C2—C6136.31 (18)C9—C10—H10120.7
O1—C2—C6114.55 (16)C11—C10—H10120.7
C2—C3—C4106.28 (17)C10—C11—C6120.82 (19)
C2—C3—C12129.79 (18)C10—C11—H11119.6
C4—C3—C12123.92 (18)C6—C11—H11119.6
C5—C4—C3106.96 (18)C17—C12—C13116.85 (18)
C5—C4—H4126.5C17—C12—C3123.72 (18)
C3—C4—H4126.5C13—C12—C3119.38 (18)
C4—C5—O1110.72 (18)C14—C13—C12119.4 (2)
C4—C5—H5124.6C14—C13—H13120.3
O1—C5—H5124.6C12—C13—H13120.3
C7—C6—C11118.14 (18)N15—C14—C13124.34 (19)
C7—C6—C2121.48 (17)N15—C14—H14117.8
C11—C6—C2120.34 (17)C13—C14—H14117.8
C8—C7—C6121.47 (18)C14—N15—C16115.86 (18)
C8—C7—H7119.3N15—C16—C17124.2 (2)
C6—C7—H7119.3N15—C16—H16117.9
C9—C8—C7117.94 (19)C17—C16—H16117.9
C9—C8—H8121.0C16—C17—C12119.35 (19)
C7—C8—H8121.0C16—C17—H17120.3
F1—C9—C8118.7 (2)C12—C17—H17120.3
F1—C9—C10118.2 (2)
C5—O1—C2—C30.5 (2)C7—C8—C9—C100.7 (4)
C5—O1—C2—C6−176.93 (18)F1—C9—C10—C11179.2 (2)
O1—C2—C3—C4−0.6 (2)C8—C9—C10—C11−1.2 (4)
C6—C2—C3—C4176.0 (2)C9—C10—C11—C60.3 (3)
O1—C2—C3—C12178.1 (2)C7—C6—C11—C101.0 (3)
C6—C2—C3—C12−5.3 (4)C2—C6—C11—C10178.8 (2)
C2—C3—C4—C50.5 (3)C2—C3—C12—C17−40.6 (3)
C12—C3—C4—C5−178.3 (2)C4—C3—C12—C17138.0 (2)
C3—C4—C5—O1−0.3 (3)C2—C3—C12—C13142.0 (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—C140.1 (3)
O1—C2—C6—C7152.23 (18)C3—C12—C13—C14177.75 (19)
C3—C2—C6—C11158.1 (2)C12—C13—C14—N150.8 (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—C171.2 (3)
C2—C6—C7—C8−179.28 (19)N15—C16—C17—C12−0.4 (3)
C6—C7—C8—C90.7 (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, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5···F1i0.952.323.006 (3)128
C8—H8···N15ii0.952.603.483 (3)155
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y+1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5···F1i0.952.323.006 (3)128
C8—H8···N15ii0.952.603.483 (3)155
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y+1/2, −z+3/2.
Acknowledgements top

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

references
References top

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761–762.

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.

Myers, M. J., Cherkofsky, S. C. & Haber, S. B. (1985). Res. Discl., 253, 223–224.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Wilkerson, W. W., Cherkofsky, S. C. & Haber, S. B. (1985). Res. Discl., 253, 220–222.