organic compounds
N-(2-Phenylimidazo[1,2-a]pyridin-3-yl)acetamide
aDépartement de Chimie, Faculté des Sciences, BP 717 Oujda, Morocco, bDépartement de Chimie, Faculté des Sciences, BP717 Oujda, Morocco, cLaboratory of Mineral Solid and Analytical Chemistry, `LMSAC', Department of Chemistry, Faculty of Sciences, University Mohamed I, PO Box 717, 60000 Oujda, Morocco, and dInstitute of Physics, Na Slovance 2, 182 21 Praha 8, Czech Republic
*Correspondence e-mail: fejfarov@fzu.cz
The 15H13N3O, 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)°.
of the title compound, CRelated literature
For general background, see Anaflous et al. (2004); Gueffier et al. (1998); Mavel et al. (2002).
Experimental
Crystal data
|
Data collection
|
Refinement
|
Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 1999); software used to prepare material for publication: JANA2006.
Supporting information
10.1107/S1600536808011501/fj2112sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808011501/fj2112Isup2.hkl
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.
Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell
CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 1999); software used to prepare material for publication: JANA2006 (Petříček et al., 2006).C15H13N3O | F(000) = 528 |
Mr = 251.3 | Dx = 1.355 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4755 reflections |
a = 13.9680 (5) Å | θ = 2.6–26.5° |
b = 5.6784 (2) Å | µ = 0.09 mm−1 |
c = 15.8145 (5) Å | T = 120 K |
β = 101.039 (3)° | Prism, colorless |
V = 1231.13 (7) Å3 | 0.58 × 0.25 × 0.17 mm |
Z = 4 |
Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector | 1544 reflections with I > 3σ(I) |
Radiation source: X-ray tube | Rint = 0.054 |
Graphite monochromator | θmax = 26.5°, θmin = 2.6° |
Detector resolution: 8.3438 pixels mm-1 | h = −17→17 |
Rotation method data acquisition using ω scans | k = −7→7 |
15703 measured reflections | l = −19→19 |
2556 independent reflections |
Refinement on F2 | 45 constraints |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.084 | Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2] |
S = 1.00 | (Δ/σ)max = 0.006 |
2556 reflections | Δρmax = 0.17 e Å−3 |
175 parameters | Δρmin = −0.14 e Å−3 |
1 restraint |
C15H13N3O | V = 1231.13 (7) Å3 |
Mr = 251.3 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.9680 (5) Å | µ = 0.09 mm−1 |
b = 5.6784 (2) Å | T = 120 K |
c = 15.8145 (5) Å | 0.58 × 0.25 × 0.17 mm |
β = 101.039 (3)° |
Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector | 1544 reflections with I > 3σ(I) |
15703 measured reflections | Rint = 0.054 |
2556 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 1 restraint |
wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.17 e Å−3 |
2556 reflections | Δρmin = −0.14 e Å−3 |
175 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 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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.61764 (8) | −0.2561 (2) | 0.47985 (7) | 0.0230 (4) | |
N2 | 0.56626 (7) | 0.05089 (18) | 0.39364 (7) | 0.0206 (4) | |
N3 | 0.70718 (11) | 0.3084 (2) | 0.41732 (9) | 0.0235 (5) | |
O1 | 0.79160 (9) | 0.1417 (2) | 0.32433 (8) | 0.0298 (4) | |
C1 | 0.69090 (11) | −0.0912 (2) | 0.48648 (9) | 0.0210 (5) | |
C2 | 0.66186 (9) | 0.09842 (19) | 0.43398 (8) | 0.0224 (4) | |
C3 | 0.54173 (10) | −0.1658 (2) | 0.42431 (9) | 0.0211 (5) | |
C4 | 0.44673 (11) | −0.2519 (3) | 0.39578 (9) | 0.0238 (5) | |
C5 | 0.38234 (11) | −0.1217 (3) | 0.33930 (9) | 0.0262 (5) | |
C6 | 0.41070 (11) | 0.0979 (2) | 0.30893 (9) | 0.0272 (5) | |
C7 | 0.50162 (10) | 0.1807 (3) | 0.33604 (9) | 0.0233 (5) | |
C8 | 0.78417 (11) | −0.1346 (2) | 0.54688 (10) | 0.0220 (6) | |
C9 | 0.79074 (12) | −0.3221 (3) | 0.60385 (10) | 0.0285 (5) | |
C10 | 0.87592 (12) | −0.3699 (3) | 0.66086 (10) | 0.0317 (5) | |
C11 | 0.95689 (11) | −0.2316 (3) | 0.66266 (10) | 0.0290 (5) | |
C12 | 0.95210 (12) | −0.0434 (3) | 0.60733 (10) | 0.0373 (6) | |
C13 | 0.86634 (12) | 0.0062 (3) | 0.54974 (11) | 0.0356 (6) | |
C14 | 0.77211 (11) | 0.3171 (3) | 0.36247 (10) | 0.0220 (5) | |
C15 | 0.81873 (12) | 0.5518 (3) | 0.35553 (11) | 0.0294 (6) | |
H3n | 0.6911 (10) | 0.4370 (19) | 0.4423 (9) | 0.0282* | |
H4 | 0.42756 | −0.400812 | 0.415958 | 0.0285* | |
H5 | 0.317152 | −0.17869 | 0.319756 | 0.0314* | |
H6 | 0.364663 | 0.187888 | 0.268776 | 0.0327* | |
H7 | 0.520896 | 0.328874 | 0.315284 | 0.028* | |
H9 | 0.734759 | −0.420445 | 0.603502 | 0.0341* | |
H10 | 0.878784 | −0.500882 | 0.699648 | 0.038* | |
H11 | 1.016393 | −0.265961 | 0.702246 | 0.0348* | |
H12 | 1.008436 | 0.054304 | 0.608524 | 0.0447* | |
H13 | 0.863646 | 0.13862 | 0.511608 | 0.0427* | |
H15a | 0.77381 | 0.67451 | 0.36305 | 0.0353* | |
H15b | 0.876474 | 0.564915 | 0.399312 | 0.0353* | |
H15c | 0.8358 (10) | 0.5666 (19) | 0.2998 (9) | 0.0353* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0273 (7) | 0.0188 (6) | 0.0250 (7) | −0.0018 (5) | 0.0100 (6) | −0.0017 (5) |
N2 | 0.0230 (7) | 0.0198 (6) | 0.0205 (6) | 0.0005 (5) | 0.0079 (5) | −0.0023 (5) |
N3 | 0.0343 (9) | 0.0126 (7) | 0.0271 (8) | −0.0014 (7) | 0.0148 (7) | −0.0020 (7) |
O1 | 0.0405 (7) | 0.0228 (6) | 0.0305 (7) | 0.0012 (6) | 0.0176 (6) | −0.0026 (5) |
C1 | 0.0263 (9) | 0.0171 (7) | 0.0225 (8) | −0.0029 (7) | 0.0119 (7) | −0.0042 (6) |
C2 | 0.0267 (8) | 0.0183 (6) | 0.0245 (7) | −0.0015 (6) | 0.0108 (6) | −0.0028 (5) |
C3 | 0.0275 (9) | 0.0186 (7) | 0.0192 (8) | 0.0014 (7) | 0.0098 (7) | −0.0021 (6) |
C4 | 0.0304 (9) | 0.0210 (8) | 0.0227 (8) | −0.0023 (7) | 0.0120 (7) | −0.0040 (6) |
C5 | 0.0217 (9) | 0.0333 (8) | 0.0247 (8) | −0.0023 (7) | 0.0074 (7) | −0.0094 (7) |
C6 | 0.0317 (8) | 0.0309 (8) | 0.0195 (8) | 0.0080 (6) | 0.0062 (7) | 0.0003 (6) |
C7 | 0.0319 (8) | 0.0197 (8) | 0.0207 (8) | 0.0027 (7) | 0.0112 (7) | −0.0005 (6) |
C8 | 0.0226 (10) | 0.0222 (8) | 0.0222 (9) | 0.0012 (7) | 0.0068 (8) | −0.0058 (7) |
C9 | 0.0296 (9) | 0.0261 (9) | 0.0308 (9) | −0.0033 (8) | 0.0086 (7) | 0.0015 (7) |
C10 | 0.0338 (9) | 0.0285 (8) | 0.0327 (9) | 0.0036 (7) | 0.0061 (8) | 0.0048 (7) |
C11 | 0.0282 (8) | 0.0324 (9) | 0.0258 (8) | 0.0039 (7) | 0.0034 (7) | −0.0015 (7) |
C12 | 0.0293 (10) | 0.0377 (9) | 0.0425 (10) | −0.0114 (8) | 0.0013 (8) | 0.0022 (7) |
C13 | 0.0394 (10) | 0.0306 (9) | 0.0357 (10) | −0.0038 (8) | 0.0040 (8) | 0.0111 (8) |
C14 | 0.0251 (10) | 0.0210 (9) | 0.0203 (8) | 0.0030 (7) | 0.0055 (7) | 0.0034 (7) |
C15 | 0.0335 (10) | 0.0248 (10) | 0.0331 (11) | −0.0032 (8) | 0.0144 (9) | 0.0020 (9) |
N1—C1 | 1.3763 (18) | C6—H6 | 0.96 |
N1—C3 | 1.3424 (17) | C7—H7 | 0.96 |
N2—C2 | 1.3916 (15) | C8—C9 | 1.387 (2) |
N2—C3 | 1.3894 (17) | C8—C13 | 1.393 (2) |
N2—C7 | 1.3689 (16) | C9—C10 | 1.375 (2) |
N3—C2 | 1.3984 (19) | C9—H9 | 0.96 |
N3—C14 | 1.371 (2) | C10—C11 | 1.373 (2) |
N3—H3n | 0.880 (12) | C10—H10 | 0.96 |
O1—C14 | 1.222 (2) | C11—C12 | 1.375 (2) |
C1—C2 | 1.3727 (18) | C11—H11 | 0.96 |
C1—C8 | 1.481 (2) | C12—C13 | 1.388 (2) |
C3—C4 | 1.405 (2) | C12—H12 | 0.96 |
C4—C5 | 1.359 (2) | C13—H13 | 0.96 |
C4—H4 | 0.96 | C14—C15 | 1.497 (2) |
C5—C6 | 1.419 (2) | C15—H15a | 0.96 |
C5—H5 | 0.96 | C15—H15b | 0.96 |
C6—C7 | 1.345 (2) | C15—H15c | 0.960 (15) |
C1—N1—C3 | 105.82 (11) | C1—C8—C9 | 119.17 (14) |
C2—N2—C3 | 106.91 (10) | C1—C8—C13 | 122.90 (14) |
C2—N2—C7 | 130.80 (11) | C9—C8—C13 | 117.93 (14) |
C3—N2—C7 | 122.27 (11) | C8—C9—C10 | 121.26 (15) |
C2—N3—C14 | 121.89 (13) | C8—C9—H9 | 119.372 |
C2—N3—H3n | 117.3 (9) | C10—C9—H9 | 119.371 |
C14—N3—H3n | 120.8 (9) | C9—C10—C11 | 120.43 (14) |
N1—C1—C2 | 110.99 (11) | C9—C10—H10 | 119.784 |
N1—C1—C8 | 119.03 (12) | C11—C10—H10 | 119.784 |
C2—C1—C8 | 129.96 (13) | C10—C11—C12 | 119.48 (13) |
N2—C2—N3 | 120.55 (11) | C10—C11—H11 | 120.26 |
N2—C2—C1 | 105.77 (11) | C12—C11—H11 | 120.259 |
N3—C2—C1 | 133.68 (12) | C11—C12—C13 | 120.42 (15) |
N1—C3—N2 | 110.49 (11) | C11—C12—H12 | 119.792 |
N1—C3—C4 | 131.02 (13) | C13—C12—H12 | 119.792 |
N2—C3—C4 | 118.48 (12) | C8—C13—C12 | 120.48 (15) |
C3—C4—C5 | 119.18 (14) | C8—C13—H13 | 119.758 |
C3—C4—H4 | 120.41 | C12—C13—H13 | 119.758 |
C5—C4—H4 | 120.41 | N3—C14—O1 | 121.32 (15) |
C4—C5—C6 | 120.52 (13) | N3—C14—C15 | 115.37 (14) |
C4—C5—H5 | 119.739 | O1—C14—C15 | 123.28 (16) |
C6—C5—H5 | 119.74 | C14—C15—H15a | 109.471 |
C5—C6—C7 | 120.46 (13) | C14—C15—H15b | 109.472 |
C5—C6—H6 | 119.768 | C14—C15—H15c | 109.5 (7) |
C7—C6—H6 | 119.769 | H15a—C15—H15b | 109.472 |
N2—C7—C6 | 119.07 (13) | H15a—C15—H15c | 109.471 |
N2—C7—H7 | 120.466 | H15b—C15—H15c | 109.47 |
C6—C7—H7 | 120.465 |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3n···N1i | 0.880 (12) | 2.162 (12) | 3.0219 (16) | 165.4 (13) |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C15H13N3O |
Mr | 251.3 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 13.9680 (5), 5.6784 (2), 15.8145 (5) |
β (°) | 101.039 (3) |
V (Å3) | 1231.13 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.58 × 0.25 × 0.17 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector |
Absorption correction | – |
No. of measured, independent and observed [I > 3σ(I)] reflections | 15703, 2556, 1544 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.084, 1.00 |
No. of reflections | 2556 |
No. of parameters | 175 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.14 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3n···N1i | 0.880 (12) | 2.162 (12) | 3.0219 (16) | 165.4 (13) |
Symmetry code: (i) x, y+1, z. |
Acknowledgements
We thank the Grant Agency of the Czech Republic for support, grant No. 202/05/0757.
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. CrossRef Google Scholar
Brandenburg, K. & Putz, H. (1999). DIAMOND. Crystal Impact GbR, 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
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. Web of Science PubMed Google Scholar
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. Web of Science CSD CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, Oxfordshire, England. Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Prague, Czech Republic. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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)°