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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3272.
Published online 2010 November 24. doi:  10.1107/S1600536810047938
PMCID: PMC3011613

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

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 [triangle]).

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Object name is e-66-o3272-scheme1.jpg

Experimental

Crystal data

  • C16H13N3O4
  • M r = 311.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3272-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.16 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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.

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 or 0.97Å and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(C) for methyl H atoms.

Figures

Fig. 1.
View of the title compound (I), with displacement ellipsoids drawn at the 40% probability level.

Crystal data

C16H13N3O4F(000) = 648
Mr = 311.29Dx = 1.393 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2224 reflections
a = 8.189 (4) Åθ = 2.2–28.2°
b = 15.821 (8) ŵ = 0.10 mm1
c = 11.884 (6) ÅT = 273 K
β = 105.380 (8)°Block, colorless
V = 1484.7 (13) Å30.26 × 0.19 × 0.13 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2618 independent reflections
Radiation source: fine-focus sealed tube1965 reflections with I > 2σ(I)
graphiteRint = 0.023
phi and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.974, Tmax = 0.987k = −18→14
7569 measured reflectionsl = −13→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.122w = 1/[σ2(Fo2) + (0.0514P)2] where P = (Fo2 + 2Fc2)/3
S = 1.38(Δ/σ)max = 0.014
2618 reflectionsΔρmax = 0.18 e Å3
209 parametersΔρmin = −0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (2)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.4896 (3)0.09876 (13)0.56705 (14)0.1106 (7)
O20.2458 (2)0.15378 (13)0.49165 (14)0.1073 (7)
O30.26198 (16)0.02576 (9)0.02277 (12)0.0718 (4)
O40.16766 (15)0.07201 (9)−0.15928 (11)0.0664 (4)
N10.3843 (3)0.12901 (12)0.48549 (16)0.0745 (5)
N20.72970 (16)0.19702 (9)−0.06373 (12)0.0490 (4)
N30.80707 (17)0.22853 (10)0.12673 (13)0.0561 (4)
C10.8789 (2)0.24074 (12)−0.04309 (17)0.0604 (5)
H10.93810.2550−0.09720.073*
C20.9223 (2)0.25889 (13)0.07191 (18)0.0617 (5)
H21.01930.28860.10960.074*
C30.6901 (2)0.19066 (11)0.04239 (14)0.0460 (4)
C40.53881 (19)0.14865 (10)0.04674 (14)0.0432 (4)
C50.4368 (2)0.11716 (11)−0.05585 (14)0.0456 (4)
C60.4823 (2)0.12748 (12)−0.16214 (14)0.0521 (5)
H60.41080.1070−0.23110.063*
C70.6262 (2)0.16622 (12)−0.16469 (15)0.0550 (5)
H70.65550.1721−0.23470.066*
C80.2819 (2)0.06715 (11)−0.05705 (15)0.0500 (4)
C90.0130 (2)0.02350 (15)−0.17049 (19)0.0762 (6)
H9A0.0405−0.0349−0.14840.091*
H9B−0.05090.0467−0.11970.091*
C10−0.0864 (3)0.02810 (19)−0.2914 (2)0.1084 (9)
H10A−0.11000.0862−0.31300.163*
H10B−0.1909−0.0019−0.30030.163*
H10C−0.02380.0031−0.34070.163*
C110.4992 (2)0.14378 (10)0.16178 (13)0.0444 (4)
C120.6133 (2)0.10865 (12)0.25694 (14)0.0534 (5)
H120.71590.08790.24900.064*
C130.5773 (2)0.10392 (12)0.36384 (15)0.0576 (5)
H130.65410.08010.42800.069*
C140.4254 (3)0.13518 (12)0.37291 (15)0.0551 (5)
C150.3104 (2)0.17153 (12)0.28087 (17)0.0606 (5)
H150.20890.19310.28970.073*
C160.3482 (2)0.17554 (12)0.17493 (15)0.0551 (5)
H160.27110.19990.11140.066*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.1407 (15)0.1542 (18)0.0415 (9)−0.0163 (13)0.0320 (10)0.0017 (10)
O20.1239 (15)0.1407 (17)0.0844 (12)−0.0061 (12)0.0754 (11)−0.0159 (10)
O30.0773 (9)0.0782 (10)0.0643 (9)−0.0097 (7)0.0263 (7)0.0181 (7)
O40.0542 (8)0.0928 (11)0.0517 (8)−0.0126 (7)0.0132 (6)0.0050 (7)
N10.1072 (15)0.0807 (13)0.0470 (11)−0.0257 (11)0.0407 (11)−0.0149 (9)
N20.0456 (8)0.0610 (9)0.0463 (9)0.0069 (7)0.0227 (7)0.0053 (7)
N30.0464 (9)0.0705 (11)0.0539 (9)0.0020 (7)0.0180 (8)−0.0055 (8)
C10.0479 (11)0.0750 (13)0.0668 (13)0.0025 (9)0.0298 (10)0.0064 (10)
C20.0440 (10)0.0723 (13)0.0731 (14)0.0006 (9)0.0230 (10)−0.0030 (10)
C30.0459 (10)0.0546 (10)0.0422 (10)0.0116 (8)0.0199 (8)0.0030 (8)
C40.0446 (9)0.0490 (10)0.0405 (9)0.0096 (7)0.0193 (8)0.0046 (7)
C50.0484 (9)0.0523 (10)0.0397 (10)0.0070 (8)0.0179 (8)0.0038 (8)
C60.0534 (10)0.0671 (12)0.0383 (10)0.0034 (9)0.0166 (8)0.0020 (8)
C70.0609 (11)0.0726 (13)0.0382 (10)0.0078 (9)0.0247 (9)0.0057 (9)
C80.0550 (11)0.0536 (11)0.0463 (11)0.0053 (8)0.0221 (9)−0.0001 (8)
C90.0588 (12)0.0869 (16)0.0848 (17)−0.0171 (11)0.0225 (11)0.0004 (12)
C100.0882 (18)0.117 (2)0.102 (2)−0.0324 (16)−0.0065 (15)0.0071 (16)
C110.0499 (10)0.0496 (10)0.0381 (9)0.0030 (8)0.0192 (8)0.0013 (7)
C120.0544 (10)0.0637 (12)0.0454 (10)0.0073 (9)0.0186 (9)0.0024 (8)
C130.0681 (12)0.0668 (12)0.0369 (10)−0.0044 (10)0.0120 (9)0.0033 (8)
C140.0756 (13)0.0571 (11)0.0410 (10)−0.0129 (10)0.0302 (9)−0.0087 (8)
C150.0675 (12)0.0658 (12)0.0605 (12)0.0065 (10)0.0380 (10)−0.0009 (10)
C160.0573 (11)0.0651 (12)0.0500 (11)0.0121 (9)0.0269 (9)0.0087 (9)

Geometric parameters (Å, °)

O1—N11.212 (2)C6—C71.336 (2)
O2—N11.221 (2)C6—H60.9300
O3—C81.199 (2)C7—H70.9300
O4—C81.324 (2)C9—C101.453 (3)
O4—C91.456 (2)C9—H9A0.9700
N1—C141.467 (2)C9—H9B0.9700
N2—C71.362 (2)C10—H10A0.9600
N2—C11.368 (2)C10—H10B0.9600
N2—C31.387 (2)C10—H10C0.9600
N3—C31.331 (2)C11—C121.379 (2)
N3—C21.368 (2)C11—C161.382 (2)
C1—C21.349 (3)C12—C131.380 (2)
C1—H10.9300C12—H120.9300
C2—H20.9300C13—C141.369 (3)
C3—C41.419 (2)C13—H130.9300
C4—C51.376 (2)C14—C151.367 (3)
C4—C111.488 (2)C15—C161.375 (2)
C5—C61.418 (2)C15—H150.9300
C5—C81.492 (2)C16—H160.9300
C8—O4—C9116.01 (15)O4—C8—C5111.70 (14)
O1—N1—O2123.67 (18)C10—C9—O4108.03 (18)
O1—N1—C14118.0 (2)C10—C9—H9A110.1
O2—N1—C14118.4 (2)O4—C9—H9A110.1
C7—N2—C1131.00 (15)C10—C9—H9B110.1
C7—N2—C3122.27 (14)O4—C9—H9B110.1
C1—N2—C3106.67 (15)H9A—C9—H9B108.4
C3—N3—C2104.42 (15)C9—C10—H10A109.5
C2—C1—N2105.78 (16)C9—C10—H10B109.5
C2—C1—H1127.1H10A—C10—H10B109.5
N2—C1—H1127.1C9—C10—H10C109.5
C1—C2—N3112.23 (17)H10A—C10—H10C109.5
C1—C2—H2123.9H10B—C10—H10C109.5
N3—C2—H2123.9C12—C11—C16119.08 (15)
N3—C3—N2110.90 (14)C12—C11—C4120.61 (15)
N3—C3—C4130.12 (15)C16—C11—C4120.30 (14)
N2—C3—C4118.97 (15)C11—C12—C13120.87 (16)
C5—C4—C3117.92 (14)C11—C12—H12119.6
C5—C4—C11124.50 (15)C13—C12—H12119.6
C3—C4—C11117.56 (15)C14—C13—C12118.25 (17)
C4—C5—C6120.44 (16)C14—C13—H13120.9
C4—C5—C8121.03 (14)C12—C13—H13120.9
C6—C5—C8118.43 (15)C15—C14—C13122.45 (16)
C7—C6—C5120.98 (17)C15—C14—N1118.81 (18)
C7—C6—H6119.5C13—C14—N1118.74 (19)
C5—C6—H6119.5C14—C15—C16118.54 (17)
C6—C7—N2119.39 (15)C14—C15—H15120.7
C6—C7—H7120.3C16—C15—H15120.7
N2—C7—H7120.3C15—C16—C11120.80 (17)
O3—C8—O4123.14 (17)C15—C16—H16119.6
O3—C8—C5125.15 (17)C11—C16—H16119.6
C7—N2—C1—C2177.07 (17)C9—O4—C8—C5178.48 (15)
C3—N2—C1—C2−0.19 (19)C4—C5—C8—O3−27.4 (3)
N2—C1—C2—N30.1 (2)C6—C5—C8—O3149.05 (18)
C3—N3—C2—C10.1 (2)C4—C5—C8—O4154.15 (15)
C2—N3—C3—N2−0.17 (18)C6—C5—C8—O4−29.4 (2)
C2—N3—C3—C4−179.10 (17)C8—O4—C9—C10−173.05 (19)
C7—N2—C3—N3−177.32 (15)C5—C4—C11—C12125.59 (19)
C1—N2—C3—N30.23 (18)C3—C4—C11—C12−56.1 (2)
C7—N2—C3—C41.7 (2)C5—C4—C11—C16−55.3 (2)
C1—N2—C3—C4179.30 (14)C3—C4—C11—C16122.98 (19)
N3—C3—C4—C5177.88 (16)C16—C11—C12—C130.9 (3)
N2—C3—C4—C5−1.0 (2)C4—C11—C12—C13−179.97 (16)
N3—C3—C4—C11−0.5 (3)C11—C12—C13—C14−0.1 (3)
N2—C3—C4—C11−179.36 (13)C12—C13—C14—C15−0.9 (3)
C3—C4—C5—C6−0.5 (2)C12—C13—C14—N1178.82 (16)
C11—C4—C5—C6177.72 (15)O1—N1—C14—C15−177.96 (19)
C3—C4—C5—C8175.81 (14)O2—N1—C14—C152.7 (3)
C11—C4—C5—C8−5.9 (2)O1—N1—C14—C132.4 (3)
C4—C5—C6—C71.4 (3)O2—N1—C14—C13−176.97 (18)
C8—C5—C6—C7−175.01 (16)C13—C14—C15—C161.0 (3)
C5—C6—C7—N2−0.7 (3)N1—C14—C15—C16−178.65 (17)
C1—N2—C7—C6−177.78 (17)C14—C15—C16—C11−0.2 (3)
C3—N2—C7—C6−0.9 (2)C12—C11—C16—C15−0.7 (3)
C9—O4—C8—O30.0 (3)C4—C11—C16—C15−179.87 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9—H9B···O3i0.972.593.295 (3)130

Symmetry codes: (i) −x, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2751).

References

  • Bruker (1998). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Jia, J., Ge, Y. Q., Tao, X. T. & Wang, J. W. (2010). Heterocycles, 81, 185–794.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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