2-Phenyl­imidazo[1,2-a]pyridine-3-carbaldehyde

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

doi:10.1107/S1600536808011306

. 2008 Apr 26;64(Pt 5):o927. doi: 10.1107/S1600536808011306

2-Phenylimidazo[1,2-a]pyridine-3-carbaldehyde

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

PMCID: PMC2961188 PMID: 21202408

Abstract

In the title compound, C₁₄H₁₀N₂O, the dihedral angle between the imidazo[1,2-a]pyridine and phenyl rings is 28.61 (4)° The molecules are connected into broad chains parallel to the a axis by weak C—H⋯O and C—H⋯N hydrogen bonds. The linking of the ribbons is provided by π–π stacking interactions between neighbouring pyridine rings, with a centroid–centroid distance of 3.7187 (7) Å.

Related literature

For general background, see Anaflous et al. (2008 ▶) and references therein. For related literature, see: Meth-Cohn & Stanforth (1991 ▶).

Experimental

Crystal data

C₁₄H₁₀N₂O
M _r = 222.2
Orthorhombic,
a = 13.0640 (3) Å
b = 7.4162 (2) Å
c = 21.6698 (6) Å
V = 2099.48 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 120 K
0.57 × 0.40 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector
Absorption correction: none
25795 measured reflections
2196 independent reflections
1305 reflections with I > 3σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.077
S = 1.04
2196 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2000 (Petříček et al., 2000 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2000.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011306/bg2180sup1.cif

e-64-0o927-sup1.cif^{(15.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011306/bg2180Isup2.hkl

e-64-0o927-Isup2.hkl^{(103.4KB, 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
C4—H4⋯N1ⁱ	0.96	2.50	3.4386 (18)	165
C6—H6⋯O1ⁱⁱ	0.96	2.46	3.1856 (16)	133

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

Acknowledgments

The Grant Agency of the Czech Republic is acknowledged for grant No 202/05/0757

supplementary crystallographic information

Comment

Functionalized imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine systems are of great interest due to their biological activities (Anaflous et al., 2008 and reference herein).

The structure of N-(2-phenylimidazo[1,2-a]pyridin-3-yl)acetamide(I) consists of isolated molecules which packing is shown in Fig. 1. The space conformation of the molecule (Fig. 2) is characterized by the dihedral angle of 28.61 (4) ° between the imidazo[1,2-a]pyridine and the phenyl rings. Weak C—H···N and C—H···O intermolecular hydrogen bonds (Table 1) connect the molecules into chains in the a direction (Fig. 3). The connection between ribbons along b (Fig. 1) is provided by π-π stacking interactions involving neighbouring pyridine rings with centroid-centroid distance 3.7187 (7) Å.

Experimental

Imidazo[1,2-a]pyridine-2-phenyl-3-carbaldehyde was synthesized according to the method described by Vilsmeier-Haack (Meth-Cohn & Stanforth, 1991) : i.e. to 1.9 g (26 mmol) of DMF cooled at 273 K, containing 4 g (26 mmol) of phosphorus oxychloride (POCl₃), was added portionwise to 10 mmole of 2-phenyl imidazo[1,2-a]pyridine. The mixture was heated at 373 K for 1 h. The solution was then neutralized at 273 K with Na₂CO₃ and extracted with Dichloromethane. The organic layer was dried over sodium sulfate and dichloromethane was removed under reduced pressure. The crude product was purified on silica gel column and imidazo[1,2-a]pyridine-2-phenyl-3-carbaldehyde was obtained in good yield (60%) as a white solid.