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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o927.
Published online 2008 April 26. doi:  10.1107/S1600536808011306
PMCID: PMC2961188

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

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 [triangle]) and references therein. For related literature, see: Meth-Cohn & Stanforth (1991 [triangle]).

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Object name is e-64-0o927-scheme1.jpg

Experimental

Crystal data

  • C14H10N2O
  • M r = 222.2
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o927-efi1.jpg
  • 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
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.16 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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.

Refinement

All the hydrogens (bonded to C atoms) were discernible in difference Fourier maps but according to standard procedures for organic compounds they were constrained to ideal positions (C-H: 0.96Å). Their isotropic atomic displacement parameters were evaluated as 1.2*Ueq of the parent atom.

Figures

Fig. 1.
Packing of of Imidazo[1,2-a]pyridine-2-phenyl-3-carbaldehyde viewed along the b axis. Hydrogen bonds are not indicated.
Fig. 2.
A molecule of the title compound, with 50% displacement ellispoids for non-H atoms.
Fig. 3.
Part of a ribbon along the a axis showing intermolecular hydrogen bonds.

Crystal data

C14H10N2OF000 = 928
Mr = 222.2Dx = 1.406 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 8746 reflections
a = 13.0640 (3) Åθ = 2.7–26.5º
b = 7.4162 (2) ŵ = 0.09 mm1
c = 21.6698 (6) ÅT = 120 K
V = 2099.48 (9) Å3Prism, colourless
Z = 80.57 × 0.40 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector2196 independent reflections
Radiation source: X-ray tube1305 reflections with I > 3σ(I)
Monochromator: graphiteRint = 0.049
Detector resolution: 8.3438 pixels mm-1θmax = 26.6º
T = 120 Kθmin = 3.1º
Rotation method data acquisition using ω scansh = −16→16
Absorption correction: nonek = −9→9
25795 measured reflectionsl = −27→27

Refinement

Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
wR(F2) = 0.077(Δ/σ)max = 0.007
S = 1.04Δρmax = 0.15 e Å3
2196 reflectionsΔρmin = −0.16 e Å3
154 parametersExtinction correction: none
36 constraints

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 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
N10.38579 (8)0.13099 (13)0.06669 (5)0.0227 (3)
N20.22707 (8)0.09004 (13)0.02784 (5)0.0204 (3)
O10.03531 (7)0.19646 (11)0.08623 (4)0.0297 (3)
C10.31590 (10)0.18666 (16)0.10870 (6)0.0208 (4)
C20.33161 (10)0.07295 (16)0.01765 (6)0.0207 (4)
C30.21543 (10)0.16659 (16)0.08658 (6)0.0204 (4)
C40.36597 (11)−0.00163 (16)−0.03801 (6)0.0235 (4)
C50.29491 (10)−0.05736 (17)−0.08037 (7)0.0243 (4)
C60.18958 (10)−0.03859 (17)−0.06861 (6)0.0247 (4)
C70.15617 (10)0.03543 (16)−0.01503 (6)0.0236 (4)
C80.35054 (10)0.25310 (16)0.16940 (6)0.0214 (4)
C90.29235 (10)0.23521 (17)0.22302 (7)0.0238 (4)
C100.32855 (11)0.30105 (17)0.27874 (7)0.0274 (5)
C110.42372 (11)0.38290 (17)0.28223 (6)0.0283 (5)
C120.48307 (11)0.39863 (17)0.22959 (6)0.0282 (4)
C130.44708 (10)0.33402 (16)0.17344 (6)0.0242 (4)
C140.11885 (10)0.22273 (16)0.11073 (7)0.0245 (4)
H40.437543−0.014444−0.0470380.0282*
H50.318903−0.109503−0.1182460.0292*
H60.139117−0.077351−0.0979540.0296*
H70.0841110.048834−0.0076450.0283*
H90.2267570.1770120.2215550.0286*
H100.2873570.2898670.3152330.0329*
H110.4484330.42850.3209180.0339*
H120.5492590.4544080.2320380.0339*
H130.4890680.3453380.1372920.0291*
H140.1086880.2870150.1486950.0294*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0207 (6)0.0225 (5)0.0249 (6)0.0004 (5)0.0004 (5)0.0017 (5)
N20.0196 (6)0.0177 (5)0.0239 (6)−0.0005 (5)−0.0001 (5)0.0031 (5)
O10.0200 (6)0.0315 (5)0.0376 (6)0.0000 (4)−0.0002 (5)0.0024 (5)
C10.0221 (7)0.0149 (7)0.0255 (8)0.0007 (6)0.0019 (6)0.0052 (6)
C20.0192 (7)0.0170 (6)0.0259 (8)−0.0002 (6)0.0015 (6)0.0051 (6)
C30.0211 (7)0.0179 (6)0.0223 (7)−0.0008 (6)0.0022 (6)0.0026 (6)
C40.0219 (8)0.0224 (7)0.0263 (8)−0.0005 (6)0.0024 (6)0.0027 (6)
C50.0281 (8)0.0201 (7)0.0248 (8)−0.0015 (6)0.0020 (6)0.0031 (6)
C60.0245 (8)0.0220 (7)0.0275 (8)−0.0044 (6)−0.0037 (6)0.0023 (6)
C70.0194 (8)0.0225 (7)0.0289 (8)−0.0025 (6)−0.0031 (6)0.0043 (6)
C80.0228 (8)0.0155 (6)0.0260 (8)0.0027 (6)−0.0010 (6)0.0032 (5)
C90.0216 (8)0.0212 (7)0.0288 (8)−0.0003 (6)−0.0001 (7)0.0034 (6)
C100.0313 (8)0.0267 (7)0.0242 (8)0.0049 (7)0.0017 (7)0.0034 (6)
C110.0330 (8)0.0255 (7)0.0263 (8)0.0053 (7)−0.0057 (7)−0.0006 (6)
C120.0266 (8)0.0242 (7)0.0339 (8)−0.0021 (6)−0.0043 (7)0.0013 (7)
C130.0243 (8)0.0222 (7)0.0263 (8)0.0009 (6)0.0007 (6)0.0032 (6)
C140.0262 (8)0.0201 (7)0.0271 (8)0.0008 (7)0.0032 (7)0.0041 (6)

Geometric parameters (Å, °)

N1—C11.3537 (16)C6—H60.9600
N1—C21.3475 (16)C7—H70.9600
N2—C21.3893 (16)C8—C91.3949 (19)
N2—C31.4020 (17)C8—C131.3994 (18)
N2—C71.3731 (17)C9—C101.386 (2)
O1—C141.2293 (16)C9—H90.9600
C1—C31.4052 (18)C10—C111.3857 (19)
C1—C81.4758 (18)C10—H100.9600
C2—C41.4008 (18)C11—C121.3840 (19)
C3—C141.4279 (18)C11—H110.9600
C4—C51.3693 (19)C12—C131.3897 (19)
C4—H40.9600C12—H120.9600
C5—C61.4063 (18)C13—H130.9600
C5—H50.9600C14—H140.9600
C6—C71.3564 (19)
C1—N1—C2105.87 (10)N2—C7—H7121.20
C2—N2—C3106.74 (10)C6—C7—H7120.02
C2—N2—C7121.92 (11)C1—C8—C9122.93 (12)
C3—N2—C7131.34 (11)C1—C8—C13118.38 (12)
N1—C1—C3111.62 (11)C9—C8—C13118.67 (12)
N1—C1—C8119.62 (11)C8—C9—C10120.43 (12)
C3—C1—C8128.74 (12)C8—C9—H9120.11
N1—C2—N2111.21 (11)C10—C9—H9119.46
N1—C2—C4129.56 (12)C9—C10—C11120.53 (13)
N2—C2—C4119.21 (11)C9—C10—H10119.74
N2—C3—C1104.54 (11)C11—C10—H10119.73
N2—C3—C14123.14 (12)C10—C11—C12119.65 (13)
C1—C3—C14132.02 (12)C10—C11—H11120.24
C2—C4—C5118.63 (12)C12—C11—H11120.11
C2—C4—H4121.78C11—C12—C13120.19 (12)
C5—C4—H4119.59C11—C12—H12119.70
C4—C5—C6120.80 (13)C13—C12—H12120.11
C4—C5—H5118.26C8—C13—C12120.50 (12)
C6—C5—H5120.94C8—C13—H13120.09
C5—C6—C7120.66 (12)C12—C13—H13119.40
C5—C6—H6121.49O1—C14—C3125.44 (13)
C7—C6—H6117.85O1—C14—H14109.03
N2—C7—C6118.78 (12)C3—C14—H14125.53

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···N1i0.962.503.4386 (18)165
C6—H6···O1ii0.962.463.1856 (16)133

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2180).

References

  • Anaflous, A., Albay, H., Benchat, N., El Bali, B., Dusek, M. & Fejfarova, K. (2008). Acta Cryst. E64, o926. [PMC free article] [PubMed]
  • Brandenburg, K. & Putz, H. (2005). DIAMOND Crystal Impact GbR, Postfach 1251, D-53002 Bonn, Germany.
  • Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst.36, 1103.
  • Meth-Cohn, O. & Stanforth, S. P. (1991). Comp. Org. Synth.2, 777–794.
  • Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
  • Petříček, V., Dušek, M. & Palatinus, L. (2000). JANA2000 Institute of Physics, Prague, Czech Republic.

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