4-[5-(4-Fluoro­phen­yl)-1H-imidazol-4-yl]pyridine

Pierre Koch; Dieter Schollmeyer; Stefan Laufer

doi:10.1107/S1600536809005650

. 2009 Feb 21;65(Pt 3):o573. doi: 10.1107/S1600536809005650

4-[5-(4-Fluorophenyl)-1H-imidazol-4-yl]pyridine

Pierre Koch ^a, Dieter Schollmeyer ^b, Stefan Laufer ^a,^*

PMCID: PMC2968498 PMID: 21582228

Abstract

In the title compound, C₁₄H₁₀FN₃, the imidazole ring makes dihedral angles of 28.2 (1) and 36.60 (9)° with the pyridine ring and the 4-fluorophenyl ring, respectively. The pyridine ring forms a dihedral angle of 44.68 (9)° with the 4-fluorophenyl ring. Intermolecular N—H⋯N hydrogen bonds are observed in the crystal structure.

Related literature

For the biological activity of the title compound, see: Liverton et al. (1999 ▶). For applications of functionalized 5(4)-(4-fluorophenyl)-4(5)-(pyridin-4-yl)imidazoles, see: Koch et al. (2008 ▶), Peifer et al. (2006 ▶).

Experimental

Crystal data

C₁₄H₁₀FN₃
M _r = 239.25
Orthorhombic,
a = 9.217 (2) Å
b = 8.1064 (5) Å
c = 30.665 (5) Å
V = 2291.1 (6) Å³
Z = 8
Cu Kα radiation
μ = 0.80 mm⁻¹
T = 193 K
0.54 × 0.20 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2121 measured reflections
2121 independent reflections
1707 reflections with I > 2σ(I)
3 standard reflections frequency: 60 min intensity decay: 2%

Refinement

R[F ² > 2σ(F ²)] = 0.076
wR(F ²) = 0.201
S = 1.09
2121 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.54 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, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005650/im2099sup1.cif

e-65-0o573-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005650/im2099Isup2.hkl

e-65-0o573-Isup2.hkl^{(104.4KB, 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
N1—H1⋯N15ⁱ	0.89	1.94	2.815 (3)	164

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

5(4)-(4-Fluorophenyl)-4(5)-(pyridin-4-yl)imidazole derivatives with various substitution patterns have been considered to be potential p38 MAP kinase inhibitors (Liverton et al. 1999, Koch et al. 2008, Peifer et al. 2006).

The molecular structure of compound I is shown in Figure 1. The imidazole ring realises dihedral angles of 28.2 (1)° and 36.60 (9)° with the pyridine ring and the 4-fluorophenyl ring, respectively. The pyridine ring encloses a dihedral angle of 44.68 (9)° with the 4-fluorophenyl ring.

The crystal packing (Figure 2) shows N1—H1 of the imidazole ring to form an intermolecular N–H···N hydrogen bond towards pyridine (N15) resulting in a infinite chain parallel to the a axis. The hydrogen bond measures 1.94 Å.

Experimental

1-(4-Fluorophenyl)-2-(pyridin-4-yl)ethane-1,2-dione (46 mg, 0.2 mmol), formaldehyde (15 µL, 0.2 mmol, 37% aq. solution), ammonium acetate (154 mg, 2.0 mmol) and 1 ml glacial acetic acid were combined in a reaction vial. The reaction vessel was heated in a CEM microwave reactor for 5 min at 453 K (initial power 200 W), after which a stream of compressed air cooled the reaction vessel. The reaction mixture was added dropwise to a concentrated NH₄OH solution at 0 °C. The formed colorless precipitate was collected by filtration, washed with water and dried (yield: 43 mg, 90%). Crystals of compound I suitable for X-ray diffraction were obtained by slow evaporation at 298 K of a solution of n-hexane - diethyl ether (3:2).