N-(2-Phenyl­imidazo[1,2-a]pyridin-3-yl)acetamide

Abderrahmane Anaflous; Hanane Albay; Nour-eddine Benchat; Brahim El Bali; Michal Dušek; Karla Fejfarová

doi:10.1107/S1600536808011501

. 2008 Apr 26;64(Pt 5):o926. doi: 10.1107/S1600536808011501

N-(2-Phenylimidazo[1,2-a]pyridin-3-yl)acetamide

Abderrahmane Anaflous ^a, Hanane Albay ^a, Nour-eddine Benchat ^b, Brahim El Bali ^c, Michal Dušek ^d, Karla Fejfarová ^d,^*

PMCID: PMC2961311 PMID: 21202407

Abstract

The crystal structure of the title compound, C₁₅H₁₃N₃O, consists of columns of molecules that are interconnected by N—H⋯N hydrogen bonds in the direction of the b axis. The torsion angle between the imidazo[1,2-a]pyridine ring system and the phenyl ring is 9.04 (5)°.

Related literature

For general background, see Anaflous et al. (2004 ▶); Gueffier et al. (1998 ▶); Mavel et al. (2002 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃O
M _r = 251.3
Monoclinic,
a = 13.9680 (5) Å
b = 5.6784 (2) Å
c = 15.8145 (5) Å
β = 101.039 (3)°
V = 1231.13 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 120 K
0.58 × 0.25 × 0.17 mm

Data collection

Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector
Absorption correction: none
15703 measured reflections
2556 independent reflections
1544 reflections with I > 3σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.084
S = 1.00
2556 reflections
175 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 1999 ▶); software used to prepare material for publication: JANA2006.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011501/fj2112sup1.cif

e-64-0o926-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011501/fj2112Isup2.hkl

e-64-0o926-Isup2.hkl^{(112.8KB, 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
N3—H3n⋯N1ⁱ	0.880 (12)	2.162 (12)	3.0219 (16)	165.4 (13)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Grant Agency of the Czech Republic for support, grant No. 202/05/0757.

supplementary crystallographic information

Comment

In recent years, functionalized imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine systems attracted persistent interest due to their biological activities (Anaflous et al., 2004 and reference herein). The screening of imidazo[1,2-a]pyridine derivatives against tuberculosis showed interesting results (Anaflous et al., 2004) and many functionalized imidazo[1,2-a]pyridines bearing a thioether side chain at the 3 position are reported as highly active against human cytomegalovirus and /or varicella-zoster virus (Gueffier et al., 1998 & Mavel et al., 2002).

We report in the present paper on the synthesis and crystal structure of N-(2-phenylimidazo[1,2-a]pyridin-3-yl)acetamide (I).

The molecules of the title compound are interconnected into columns extended along b by an N3—H3n···N1 hydrogen bonds (see Tab. 1). No bonding has been found between the columns that appear to be quite isolated.

Bonds and angles values are usual as those reported in similar compounds.

The torsion angle between the imidazo[1,2-a]pyridine and phenyl ring is 9.04 (5)°

Experimental

The commercially available 2-phenylimidazo[1,2-a]pyridin-3-amine (0.50 g, 2.4 mmole) in toluene (10 ml, 94 mmole) was treated with acetic anhydride (0.3 ml, 3.2 mmole). The mixture was stirred for two hours. Toluene was eliminated under reduced pressure and the residue was washed with water to give, after drying, 0.45 g (1.8 mmole) of N-(2-phenylimidazo[1,2-a]pyridin-3-yl)acetamide as colorless crystals.