organic compounds
2-Phenylimidazo[1,2-a]pyridine-3-carbaldehyde
aDépartement de Chimie, Faculté des Sciences, BP 717, 60000 Oujda, Morocco, bLaboratory of Mineral Solid and Analytical Chemistry, `LMSAC', Department of Chemistry, Faculty of Sciences, University Mohamed I, PO Box 717, 60000 Oujda, Morocco, and cInstitute of Physics, Na Slovance 2, 182 21 Praha 8, Czech Republic
*Correspondence e-mail: fejfarov@fzu.cz
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
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Data collection
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell 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.
Supporting information
10.1107/S1600536808011306/bg2180sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808011306/bg2180Isup2.hkl
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.
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.
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell
CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); 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 (Petříček et al., 2000).C14H10N2O | F(000) = 928 |
Mr = 222.2 | Dx = 1.406 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 8746 reflections |
a = 13.0640 (3) Å | θ = 2.7–26.5° |
b = 7.4162 (2) Å | µ = 0.09 mm−1 |
c = 21.6698 (6) Å | T = 120 K |
V = 2099.48 (9) Å3 | Prism, colourless |
Z = 8 | 0.57 × 0.40 × 0.24 mm |
Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector | 1305 reflections with I > 3σ(I) |
Radiation source: X-ray tube | Rint = 0.049 |
Graphite monochromator | θmax = 26.6°, θmin = 3.1° |
Detector resolution: 8.3438 pixels mm-1 | h = −16→16 |
Rotation method data acquisition using ω scans | k = −9→9 |
25795 measured reflections | l = −27→27 |
2196 independent reflections |
Refinement on F2 | 36 constraints |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.077 | Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2] |
S = 1.04 | (Δ/σ)max = 0.007 |
2196 reflections | Δρmax = 0.15 e Å−3 |
154 parameters | Δρmin = −0.16 e Å−3 |
0 restraints |
C14H10N2O | V = 2099.48 (9) Å3 |
Mr = 222.2 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 13.0640 (3) Å | µ = 0.09 mm−1 |
b = 7.4162 (2) Å | T = 120 K |
c = 21.6698 (6) Å | 0.57 × 0.40 × 0.24 mm |
Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector | 1305 reflections with I > 3σ(I) |
25795 measured reflections | Rint = 0.049 |
2196 independent reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.15 e Å−3 |
2196 reflections | Δρmin = −0.16 e Å−3 |
154 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.38579 (8) | 0.13099 (13) | 0.06669 (5) | 0.0227 (3) | |
N2 | 0.22707 (8) | 0.09004 (13) | 0.02784 (5) | 0.0204 (3) | |
O1 | 0.03531 (7) | 0.19646 (11) | 0.08623 (4) | 0.0297 (3) | |
C1 | 0.31590 (10) | 0.18666 (16) | 0.10870 (6) | 0.0208 (4) | |
C2 | 0.33161 (10) | 0.07295 (16) | 0.01765 (6) | 0.0207 (4) | |
C3 | 0.21543 (10) | 0.16659 (16) | 0.08658 (6) | 0.0204 (4) | |
C4 | 0.36597 (11) | −0.00163 (16) | −0.03801 (6) | 0.0235 (4) | |
C5 | 0.29491 (10) | −0.05736 (17) | −0.08037 (7) | 0.0243 (4) | |
C6 | 0.18958 (10) | −0.03859 (17) | −0.06861 (6) | 0.0247 (4) | |
C7 | 0.15617 (10) | 0.03543 (16) | −0.01503 (6) | 0.0236 (4) | |
C8 | 0.35054 (10) | 0.25310 (16) | 0.16940 (6) | 0.0214 (4) | |
C9 | 0.29235 (10) | 0.23521 (17) | 0.22302 (7) | 0.0238 (4) | |
C10 | 0.32855 (11) | 0.30105 (17) | 0.27874 (7) | 0.0274 (5) | |
C11 | 0.42372 (11) | 0.38290 (17) | 0.28223 (6) | 0.0283 (5) | |
C12 | 0.48307 (11) | 0.39863 (17) | 0.22959 (6) | 0.0282 (4) | |
C13 | 0.44708 (10) | 0.33402 (16) | 0.17344 (6) | 0.0242 (4) | |
C14 | 0.11885 (10) | 0.22273 (16) | 0.11073 (7) | 0.0245 (4) | |
H4 | 0.437543 | −0.014444 | −0.047038 | 0.0282* | |
H5 | 0.318903 | −0.109503 | −0.118246 | 0.0292* | |
H6 | 0.139117 | −0.077351 | −0.097954 | 0.0296* | |
H7 | 0.084111 | 0.048834 | −0.007645 | 0.0283* | |
H9 | 0.226757 | 0.177012 | 0.221555 | 0.0286* | |
H10 | 0.287357 | 0.289867 | 0.315233 | 0.0329* | |
H11 | 0.448433 | 0.4285 | 0.320918 | 0.0339* | |
H12 | 0.549259 | 0.454408 | 0.232038 | 0.0339* | |
H13 | 0.489068 | 0.345338 | 0.137292 | 0.0291* | |
H14 | 0.108688 | 0.287015 | 0.148695 | 0.0294* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0207 (6) | 0.0225 (5) | 0.0249 (6) | 0.0004 (5) | 0.0004 (5) | 0.0017 (5) |
N2 | 0.0196 (6) | 0.0177 (5) | 0.0239 (6) | −0.0005 (5) | −0.0001 (5) | 0.0031 (5) |
O1 | 0.0200 (6) | 0.0315 (5) | 0.0376 (6) | 0.0000 (4) | −0.0002 (5) | 0.0024 (5) |
C1 | 0.0221 (7) | 0.0149 (7) | 0.0255 (8) | 0.0007 (6) | 0.0019 (6) | 0.0052 (6) |
C2 | 0.0192 (7) | 0.0170 (6) | 0.0259 (8) | −0.0002 (6) | 0.0015 (6) | 0.0051 (6) |
C3 | 0.0211 (7) | 0.0179 (6) | 0.0223 (7) | −0.0008 (6) | 0.0022 (6) | 0.0026 (6) |
C4 | 0.0219 (8) | 0.0224 (7) | 0.0263 (8) | −0.0005 (6) | 0.0024 (6) | 0.0027 (6) |
C5 | 0.0281 (8) | 0.0201 (7) | 0.0248 (8) | −0.0015 (6) | 0.0020 (6) | 0.0031 (6) |
C6 | 0.0245 (8) | 0.0220 (7) | 0.0275 (8) | −0.0044 (6) | −0.0037 (6) | 0.0023 (6) |
C7 | 0.0194 (8) | 0.0225 (7) | 0.0289 (8) | −0.0025 (6) | −0.0031 (6) | 0.0043 (6) |
C8 | 0.0228 (8) | 0.0155 (6) | 0.0260 (8) | 0.0027 (6) | −0.0010 (6) | 0.0032 (5) |
C9 | 0.0216 (8) | 0.0212 (7) | 0.0288 (8) | −0.0003 (6) | −0.0001 (7) | 0.0034 (6) |
C10 | 0.0313 (8) | 0.0267 (7) | 0.0242 (8) | 0.0049 (7) | 0.0017 (7) | 0.0034 (6) |
C11 | 0.0330 (8) | 0.0255 (7) | 0.0263 (8) | 0.0053 (7) | −0.0057 (7) | −0.0006 (6) |
C12 | 0.0266 (8) | 0.0242 (7) | 0.0339 (8) | −0.0021 (6) | −0.0043 (7) | 0.0013 (7) |
C13 | 0.0243 (8) | 0.0222 (7) | 0.0263 (8) | 0.0009 (6) | 0.0007 (6) | 0.0032 (6) |
C14 | 0.0262 (8) | 0.0201 (7) | 0.0271 (8) | 0.0008 (7) | 0.0032 (7) | 0.0041 (6) |
N1—C1 | 1.3537 (16) | C6—H6 | 0.9600 |
N1—C2 | 1.3475 (16) | C7—H7 | 0.9600 |
N2—C2 | 1.3893 (16) | C8—C9 | 1.3949 (19) |
N2—C3 | 1.4020 (17) | C8—C13 | 1.3994 (18) |
N2—C7 | 1.3731 (17) | C9—C10 | 1.386 (2) |
O1—C14 | 1.2293 (16) | C9—H9 | 0.9600 |
C1—C3 | 1.4052 (18) | C10—C11 | 1.3857 (19) |
C1—C8 | 1.4758 (18) | C10—H10 | 0.9600 |
C2—C4 | 1.4008 (18) | C11—C12 | 1.3840 (19) |
C3—C14 | 1.4279 (18) | C11—H11 | 0.9600 |
C4—C5 | 1.3693 (19) | C12—C13 | 1.3897 (19) |
C4—H4 | 0.9600 | C12—H12 | 0.9600 |
C5—C6 | 1.4063 (18) | C13—H13 | 0.9600 |
C5—H5 | 0.9600 | C14—H14 | 0.9600 |
C6—C7 | 1.3564 (19) | ||
C1—N1—C2 | 105.87 (10) | N2—C7—H7 | 121.20 |
C2—N2—C3 | 106.74 (10) | C6—C7—H7 | 120.02 |
C2—N2—C7 | 121.92 (11) | C1—C8—C9 | 122.93 (12) |
C3—N2—C7 | 131.34 (11) | C1—C8—C13 | 118.38 (12) |
N1—C1—C3 | 111.62 (11) | C9—C8—C13 | 118.67 (12) |
N1—C1—C8 | 119.62 (11) | C8—C9—C10 | 120.43 (12) |
C3—C1—C8 | 128.74 (12) | C8—C9—H9 | 120.11 |
N1—C2—N2 | 111.21 (11) | C10—C9—H9 | 119.46 |
N1—C2—C4 | 129.56 (12) | C9—C10—C11 | 120.53 (13) |
N2—C2—C4 | 119.21 (11) | C9—C10—H10 | 119.74 |
N2—C3—C1 | 104.54 (11) | C11—C10—H10 | 119.73 |
N2—C3—C14 | 123.14 (12) | C10—C11—C12 | 119.65 (13) |
C1—C3—C14 | 132.02 (12) | C10—C11—H11 | 120.24 |
C2—C4—C5 | 118.63 (12) | C12—C11—H11 | 120.11 |
C2—C4—H4 | 121.78 | C11—C12—C13 | 120.19 (12) |
C5—C4—H4 | 119.59 | C11—C12—H12 | 119.70 |
C4—C5—C6 | 120.80 (13) | C13—C12—H12 | 120.11 |
C4—C5—H5 | 118.26 | C8—C13—C12 | 120.50 (12) |
C6—C5—H5 | 120.94 | C8—C13—H13 | 120.09 |
C5—C6—C7 | 120.66 (12) | C12—C13—H13 | 119.40 |
C5—C6—H6 | 121.49 | O1—C14—C3 | 125.44 (13) |
C7—C6—H6 | 117.85 | O1—C14—H14 | 109.03 |
N2—C7—C6 | 118.78 (12) | C3—C14—H14 | 125.53 |
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 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C14H10N2O |
Mr | 222.2 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 120 |
a, b, c (Å) | 13.0640 (3), 7.4162 (2), 21.6698 (6) |
V (Å3) | 2099.48 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.57 × 0.40 × 0.24 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector |
Absorption correction | – |
No. of measured, independent and observed [I > 3σ(I)] reflections | 25795, 2196, 1305 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.629 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.077, 1.04 |
No. of reflections | 2196 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.16 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SIR2002 (Burla et al., 2003), JANA2000 (Petříček et al., 2000), DIAMOND (Brandenburg & Putz, 2005).
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 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z. |
Acknowledgements
The Grant Agency of the Czech Republic is acknowledged for grant No 202/05/0757
References
Anaflous, A., Albay, H., Benchat, N., El Bali, B., Dusek, M. & Fejfarova, K. (2008). Acta Cryst. E64, o926. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Postfach 1251, D-53002 Bonn, Germany. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. CrossRef IUCr Journals Google Scholar
Meth-Cohn, O. & Stanforth, S. P. (1991). Comp. Org. Synth. 2, 777–794. Google Scholar
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2000). JANA2000. Institute of Physics, Prague, Czech Republic. Google Scholar
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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.