4-[2-(4-Fluoro­phen­yl)-1H-pyrrol-3-yl]pyridine

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

doi:10.1107/S160053680900364X

. 2009 Feb 4;65(Pt 3):o457. doi: 10.1107/S160053680900364X

4-[2-(4-Fluorophenyl)-1H-pyrrol-3-yl]pyridine

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

PMCID: PMC2968667 PMID: 21582129

Abstract

In the crystal structure of the title compound, C₁₅H₁₁FN₂, the pyrrole ring makes dihedral angles of 33.19 (9) and 36.33 (10)° with the pyridine and 4-fluorophenyl rings, respectively. The pyridine ring makes a dihedral angle of 46.59 (9)° with the 4-fluorophenyl ring. In the crystal structure, an N—H⋯N hydrogen bond joins the molecules into chains.

Related literature

Many 1-(4-fluorophenyl)-2-(pyridin-4-yl)pyrrol derivatives have been prepared and their biological activities studied; see: de Laszlo et al. (1998 ▶); Revesz et al. (2000 ▶, 2002 ▶); Qian et al. (2006 ▶). For the synthesis of the title compound, see: Qian et al. (2006 ▶).

Experimental

Crystal data

C₁₅H₁₁FN₂
M _r = 238.26
Orthorhombic,
a = 9.2966 (7) Å
b = 8.1966 (5) Å
c = 30.5738 (19) Å
V = 2329.7 (3) Å³
Z = 8
Cu Kα radiation
μ = 0.76 mm⁻¹
T = 193 (2) K
0.25 × 0.20 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2175 measured reflections
2175 independent reflections
1744 reflections with I > 2σ(I)
3 standard reflections frequency: 60 min intensity decay: 2%

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.120
S = 1.03
2175 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.17 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/S160053680900364X/bt2858sup1.cif

e-65-0o457-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900364X/bt2858Isup2.hkl

e-65-0o457-Isup2.hkl^{(107.1KB, 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⋯N16ⁱ	0.93	1.97	2.8696 (19)	161

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Functionalized 1-(4-fluorophenyl)-2-(pyridin-4-yl)pyrrols can be used as anticoccidial agents (Qian et al. 2006) or as p38 MAP kinase inhibitors (de Laszlo et al. 1998; Revesz et al. 2000, 2002).

The analysis of the crystal structure of the title compound is shown in Fig. 1. The pyrrole ring makes dihedral angles of 33.19 (9)° and 36.33 (10)° to the pyridine ring and the 4-fluorophenyl ring, respectively. The pyridine ring makes a dihedral angle of 46.59 (9)° to the 4-fluorophenyl ring.

The crystal packing (Fig. 2) shows that N1—H1 of the pyrrole ring forms an intermolecular N—H···N hydrogen bond to the pyridine ring (N16) resulting in a chain parallel to the a axis.

Experimental

Ammonium acetate (2.20 g, 34.9 mmol) was added to a solution of 4-(4-fluorophenyl)-4-oxo-3-(pyridin-4-yl)butanal (0.50 g) in glacial acetic acid (10 ml). The resulting mixture was heated to 388–393 K for 2 h. The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate and aq. NaHCO₃ solution. Solid Na₂CO₃ was added until effervescence ceased. The organic phase was washed with aq. NaHCO₃ solution and brine, dried over Na₂SO₄ and the solvent was evaporated under reduced pressure to give crude I. The residue was dissolved in ethyl acetate (7 ml) and filtered, then purified by flash chromatography (SiO₂, petroleum ether/ethyl acetate 1:1 to 1:4). Yield 135 mg. For X-ray suitable crystals of compound I were obtained by slow evaporation at 298 K of a solution of n-hexane–ethyl acetate.