Ethyl 8-(4-nitro­phen­yl)imidazo[1,2-a]pyridine-7-carboxyl­ate

Gui-Yun Duan; Yu-Juan Zhang; Ben-Qian Hao

doi:10.1107/S1600536810047938

. 2010 Nov 24;66(Pt 12):o3272. doi: 10.1107/S1600536810047938

Ethyl 8-(4-nitrophenyl)imidazo[1,2-a]pyridine-7-carboxylate

Gui-Yun Duan ^a,^*, Yu-Juan Zhang ^a, Ben-Qian Hao ^a

PMCID: PMC3011613 PMID: 21589555

Abstract

In the title compound, C₁₆H₁₃N₃O₄, the imidazo[1,2-a]pyridine and benzene rings make a dihedral angle of 56.21 (2)°. The crystal packing is stabilized by weak π–π stacking interactions [centroid–centroid distances = 3.787 (2) Å] and C—H⋯O intermolecular hydrogen-bonding interactions.

Related literature

For applications of imidazo[1,2-a]pyridine-containing compounds, see: Jia et al. (2010 ▶).

Experimental

Crystal data

C₁₆H₁₃N₃O₄
M _r = 311.29
Monoclinic,
a = 8.189 (4) Å
b = 15.821 (8) Å
c = 11.884 (6) Å
β = 105.380 (8)°
V = 1484.7 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 K
0.26 × 0.19 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.974, T _max = 0.987
7569 measured reflections
2618 independent reflections
1965 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.122
S = 1.38
2618 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047938/hg2751sup1.cif

e-66-o3272-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047938/hg2751Isup2.hkl

e-66-o3272-Isup2.hkl^{(128.6KB, 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
C9—H9B⋯O3ⁱ	0.97	2.59	3.295 (3)	130

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Natural Science Fund of Shandong Province (Y2007C135).

supplementary crystallographic information

Comment

The imidazo[1,2-a]pyridines (IP) have attracted considerable attention because of their wide range of pharmacological activities such as antiviral, antibacterial, antifungal, antiulcer, and anti-inflammatory behavior (Jia et al., 2010). Drugs containing imidazo[1,2-a]pyridines such as Alpidem, Zolpidem, Necopidem, Olprinone, Divalpon and Zolimidine are currently available on the market. In continuation of our work in this direction, we report here the crystal structure of the title compound, (I).

The title compound, C₁₆H₁₃N₃O₄, the imidazo[1,2-a]pyridine ring (N2/N3/C1—C7) and benzene ring (C11—C16) make a dihedral angles of 56.21 (2) °. π—π interactions are indicated by the short distance (Cg1···Cg2 distance of 3.787 (2) Å, symmetry code: x,1/2 - y,-1/2 + z) between the centroids of the pyridine ring (N2/C3—C7) (Cg1) and benzene ring C11—C16 (Cg2) (Table 1). There are weaker C—H···O intermolecular interactions, which stabilize the structure (Table 1).

Experimental

To a 50-ml round-bottomed flask were added ethyl 4-bromobut-2-enoate (1.20 mmol), (1H-imidazol-2-yl)(4-nitrophenyl)methanone (1.00 mmol), potassium carbonate (0.283 g, 2.05 mmol) and dry DMF (10 ml). The mixture was stirred at rt for 3 h and then filtered. The filtrate was poured into water (100 ml) and extracted with CH₂Cl₂ (three times per 30 ml). The combined extracts were washed with water, dried over anhydrous MgSO₄ and filtered, and the solvent was removed by rotary evaporation. The crude product were purified by column chromatography. Crystals of (I) suitable for X-ray diffraction was obtained by slow evaporation of a solution of the product in ethyl acetate at room temperature for 2 d.