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

Bassam Abu Thaher; Pierre Koch; Dieter Schollmeyer; Stefan Laufer

doi:10.1107/S1600536809003651

. 2009 Feb 4;65(Pt 3):o458. doi: 10.1107/S1600536809003651

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

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

PMCID: PMC2968695 PMID: 21582130

Abstract

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,
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[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 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

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.

Supplementary Material

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

e-65-0o458-sup1.cif^{(17.2KB, cif)}

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

e-65-0o458-Isup2.hkl^{(106.8KB, hkl)}

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
C5—H5⋯F1ⁱ	0.95	2.32	3.006 (3)	128
C8—H8⋯N15ⁱⁱ	0.95	2.60	3.483 (3)	155

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.