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

Anaflous, A.; Albay, H.; Benchat, N.; El Bali, B.; Dušek, M.; Fejfarová, K.

doi:10.1107/S1600536808011501

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o926

doi:10.1107/S1600536808011501

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

Abderrahmane Anaflous,^a Hanane Albay,^a Nour-eddine Benchat,^b Brahim El Bali,^c Michal Dušek ^d and Karla Fejfarová ^d ^*

^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

(Received 7 April 2008; accepted 22 April 2008; online 26 April 2008)

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 ); Gueffier et al. (1998 ); Mavel et al. (2002 ).

Experimental

Crystal data

C₁₅H₁₃N₃O
M_r = 251.3
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.084
S = 1.00
2556 reflections
175 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, Oxfordshire, England.]$ ); 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

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

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

checkCIF report

Comment top

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)°

Related literature top

For general background, see Anaflous et al. (2004); Gueffier et al. (1998); Mavel et al. (2002)

Experimental top

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.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: 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).

Figures top

	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

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

Crystal data top

C₁₅H₁₃N₃O	F(000) = 528
M_r = 251.3	D_x = 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

Data collection top

Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector	1544 reflections with I > 3σ(I)
Radiation source: X-ray tube	R_int = 0.054
Graphite monochromator	θ_max = 26.5°, θ_min = 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 top

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	Δρ_max = 0.17 e Å⁻³
175 parameters	Δρ_min = −0.14 e Å⁻³
1 restraint

Crystal data top

C₁₅H₁₃N₃O	V = 1231.13 (7) Å³
M_r = 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)°

Data collection top

Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector	1544 reflections with I > 3σ(I)
15703 measured reflections	R_int = 0.054
2556 independent reflections

Refinement top

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	Δρ_max = 0.17 e Å⁻³
2556 reflections	Δρ_min = −0.14 e Å⁻³
175 parameters

Special details top

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*U_eq 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) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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