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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o926.
Published online 2008 April 26. doi:  10.1107/S1600536808011501
PMCID: PMC2961311

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

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 [triangle]); Gueffier et al. (1998 [triangle]); Mavel et al. (2002 [triangle]).

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Object name is e-64-0o926-scheme1.jpg

Experimental

Crystal data

  • C15H13N3O
  • M r = 251.3
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o926-efi1.jpg
  • 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
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.14 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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.

Figures

Fig. 1.
View of the unit cell of the title structure along the axis b
Fig. 2.
Asymetric unit of title compound, showing 50% displacement ellispoids for non-H atoms.
Fig. 3.
The columns of molecules showing N—H···N hydrogen bonds

Crystal data

C15H13N3OF000 = 528
Mr = 251.3Dx = 1.355 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4755 reflections
a = 13.9680 (5) Åθ = 2.6–26.5º
b = 5.6784 (2) ŵ = 0.09 mm1
c = 15.8145 (5) ÅT = 120 K
β = 101.039 (3)ºPrism, colorless
V = 1231.13 (7) Å30.58 × 0.25 × 0.17 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector2556 independent reflections
Radiation source: X-ray tube1544 reflections with I > 3σ(I)
Monochromator: graphiteRint = 0.054
Detector resolution: 8.3438 pixels mm-1θmax = 26.5º
T = 120 Kθmin = 2.6º
Rotation method data acquisition using ω scansh = −17→17
Absorption correction: nonek = −7→7
15703 measured reflectionsl = −19→19

Refinement

Refinement on F245 constraints
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
S = 1.00(Δ/σ)max = 0.006
2556 reflectionsΔρmax = 0.17 e Å3
175 parametersΔρmin = −0.14 e Å3
1 restraintExtinction correction: none

Special details

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.All the H atoms were discernible in difference Fourier maps and could be refined to reasonable geometry. According to standard procedures for organic compounds the H atoms bonded to C atoms were constrained to ideal positions. The N—H distances were restrained to 0.87 Å with σ 0.01. The isotropic atomic displacement parameters of hydrogen atoms were evaluated as 1.2*Ueq of the parent atom.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

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

xyzUiso*/Ueq
N10.61764 (8)−0.2561 (2)0.47985 (7)0.0230 (4)
N20.56626 (7)0.05089 (18)0.39364 (7)0.0206 (4)
N30.70718 (11)0.3084 (2)0.41732 (9)0.0235 (5)
O10.79160 (9)0.1417 (2)0.32433 (8)0.0298 (4)
C10.69090 (11)−0.0912 (2)0.48648 (9)0.0210 (5)
C20.66186 (9)0.09842 (19)0.43398 (8)0.0224 (4)
C30.54173 (10)−0.1658 (2)0.42431 (9)0.0211 (5)
C40.44673 (11)−0.2519 (3)0.39578 (9)0.0238 (5)
C50.38234 (11)−0.1217 (3)0.33930 (9)0.0262 (5)
C60.41070 (11)0.0979 (2)0.30893 (9)0.0272 (5)
C70.50162 (10)0.1807 (3)0.33604 (9)0.0233 (5)
C80.78417 (11)−0.1346 (2)0.54688 (10)0.0220 (6)
C90.79074 (12)−0.3221 (3)0.60385 (10)0.0285 (5)
C100.87592 (12)−0.3699 (3)0.66086 (10)0.0317 (5)
C110.95689 (11)−0.2316 (3)0.66266 (10)0.0290 (5)
C120.95210 (12)−0.0434 (3)0.60733 (10)0.0373 (6)
C130.86634 (12)0.0062 (3)0.54974 (11)0.0356 (6)
C140.77211 (11)0.3171 (3)0.36247 (10)0.0220 (5)
C150.81873 (12)0.5518 (3)0.35553 (11)0.0294 (6)
H3n0.6911 (10)0.4370 (19)0.4423 (9)0.0282*
H40.42756−0.4008120.4159580.0285*
H50.317152−0.178690.3197560.0314*
H60.3646630.1878880.2687760.0327*
H70.5208960.3288740.3152840.028*
H90.734759−0.4204450.6035020.0341*
H100.878784−0.5008820.6996480.038*
H111.016393−0.2659610.7022460.0348*
H121.0084360.0543040.6085240.0447*
H130.8636460.138620.5116080.0427*
H15a0.773810.674510.363050.0353*
H15b0.8764740.5649150.3993120.0353*
H15c0.8358 (10)0.5666 (19)0.2998 (9)0.0353*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0273 (7)0.0188 (6)0.0250 (7)−0.0018 (5)0.0100 (6)−0.0017 (5)
N20.0230 (7)0.0198 (6)0.0205 (6)0.0005 (5)0.0079 (5)−0.0023 (5)
N30.0343 (9)0.0126 (7)0.0271 (8)−0.0014 (7)0.0148 (7)−0.0020 (7)
O10.0405 (7)0.0228 (6)0.0305 (7)0.0012 (6)0.0176 (6)−0.0026 (5)
C10.0263 (9)0.0171 (7)0.0225 (8)−0.0029 (7)0.0119 (7)−0.0042 (6)
C20.0267 (8)0.0183 (6)0.0245 (7)−0.0015 (6)0.0108 (6)−0.0028 (5)
C30.0275 (9)0.0186 (7)0.0192 (8)0.0014 (7)0.0098 (7)−0.0021 (6)
C40.0304 (9)0.0210 (8)0.0227 (8)−0.0023 (7)0.0120 (7)−0.0040 (6)
C50.0217 (9)0.0333 (8)0.0247 (8)−0.0023 (7)0.0074 (7)−0.0094 (7)
C60.0317 (8)0.0309 (8)0.0195 (8)0.0080 (6)0.0062 (7)0.0003 (6)
C70.0319 (8)0.0197 (8)0.0207 (8)0.0027 (7)0.0112 (7)−0.0005 (6)
C80.0226 (10)0.0222 (8)0.0222 (9)0.0012 (7)0.0068 (8)−0.0058 (7)
C90.0296 (9)0.0261 (9)0.0308 (9)−0.0033 (8)0.0086 (7)0.0015 (7)
C100.0338 (9)0.0285 (8)0.0327 (9)0.0036 (7)0.0061 (8)0.0048 (7)
C110.0282 (8)0.0324 (9)0.0258 (8)0.0039 (7)0.0034 (7)−0.0015 (7)
C120.0293 (10)0.0377 (9)0.0425 (10)−0.0114 (8)0.0013 (8)0.0022 (7)
C130.0394 (10)0.0306 (9)0.0357 (10)−0.0038 (8)0.0040 (8)0.0111 (8)
C140.0251 (10)0.0210 (9)0.0203 (8)0.0030 (7)0.0055 (7)0.0034 (7)
C150.0335 (10)0.0248 (10)0.0331 (11)−0.0032 (8)0.0144 (9)0.0020 (9)

Geometric parameters (Å, °)

N1—C11.3763 (18)C6—H60.96
N1—C31.3424 (17)C7—H70.96
N2—C21.3916 (15)C8—C91.387 (2)
N2—C31.3894 (17)C8—C131.393 (2)
N2—C71.3689 (16)C9—C101.375 (2)
N3—C21.3984 (19)C9—H90.96
N3—C141.371 (2)C10—C111.373 (2)
N3—H3n0.880 (12)C10—H100.96
O1—C141.222 (2)C11—C121.375 (2)
C1—C21.3727 (18)C11—H110.96
C1—C81.481 (2)C12—C131.388 (2)
C3—C41.405 (2)C12—H120.96
C4—C51.359 (2)C13—H130.96
C4—H40.96C14—C151.497 (2)
C5—C61.419 (2)C15—H15a0.96
C5—H50.96C15—H15b0.96
C6—C71.345 (2)C15—H15c0.960 (15)
C1—N1—C3105.82 (11)C1—C8—C9119.17 (14)
C2—N2—C3106.91 (10)C1—C8—C13122.90 (14)
C2—N2—C7130.80 (11)C9—C8—C13117.93 (14)
C3—N2—C7122.27 (11)C8—C9—C10121.26 (15)
C2—N3—C14121.89 (13)C8—C9—H9119.372
C2—N3—H3n117.3 (9)C10—C9—H9119.371
C14—N3—H3n120.8 (9)C9—C10—C11120.43 (14)
N1—C1—C2110.99 (11)C9—C10—H10119.784
N1—C1—C8119.03 (12)C11—C10—H10119.784
C2—C1—C8129.96 (13)C10—C11—C12119.48 (13)
N2—C2—N3120.55 (11)C10—C11—H11120.26
N2—C2—C1105.77 (11)C12—C11—H11120.259
N3—C2—C1133.68 (12)C11—C12—C13120.42 (15)
N1—C3—N2110.49 (11)C11—C12—H12119.792
N1—C3—C4131.02 (13)C13—C12—H12119.792
N2—C3—C4118.48 (12)C8—C13—C12120.48 (15)
C3—C4—C5119.18 (14)C8—C13—H13119.758
C3—C4—H4120.41C12—C13—H13119.758
C5—C4—H4120.41N3—C14—O1121.32 (15)
C4—C5—C6120.52 (13)N3—C14—C15115.37 (14)
C4—C5—H5119.739O1—C14—C15123.28 (16)
C6—C5—H5119.74C14—C15—H15a109.471
C5—C6—C7120.46 (13)C14—C15—H15b109.472
C5—C6—H6119.768C14—C15—H15c109.5 (7)
C7—C6—H6119.769H15a—C15—H15b109.472
N2—C7—C6119.07 (13)H15a—C15—H15c109.471
N2—C7—H7120.466H15b—C15—H15c109.47
C6—C7—H7120.465

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3n···N1i0.880 (12)2.162 (12)3.0219 (16)165.4 (13)

Symmetry codes: (i) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2112).

References

  • Anaflous, A., Benchat, N., Mimouni, M., Abouricha, S., Ben-Hadda, T., El Bali, B., Hakkou, A. & Hacht, B. (2004). Lett. Drug Des. Discovery, 1, 224—229.
  • Brandenburg, K. & Putz, H. (1999). DIAMOND Crystal Impact GbR, Bonn, Germany.
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  • Gueffier, A., Mavel, S., Lhassani, M., Elhakmaoui, A., Snoeck, R., Andrei, G., Chavignon, O., Teulade, J. C., Witvrouw, M., Balzarini, J., De Clercq, E. & Chapat, J. (1998). J. Med. Chem.41, 5108–5112. [PubMed]
  • Mavel, S., Renou, J. L., Galtier, C., Allouchi, H., Snoeck, R., Andrei, G., Balzarini, J., Gueffier, A. & De Clercq, E. (2002). Bioorg. Med Chem.10, 941–946. [PubMed]
  • Oxford Diffraction (2008). CrysAlis CCD andCrysAlis RED Oxford Diffraction Ltd., Abingdon, Oxfordshire, England.
  • Petříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006 Institute of Physics, Prague, Czech Republic.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography