N-(2-Phenyl-imidazo[1,2-a]pyridin-3-yl)acetamide.

The crystal structure of the title compound, C(15)H(13)N(3)O, consists of columns of mol-ecules that are inter-connected 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 = 251.3

Monoclinic,

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 ▶); cell refinement: 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.

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

C15H13N3O	F000 = 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 = 2.6–26.5º
b = 5.6784 (2) Å	µ = 0.09 mm−1
c = 15.8145 (5) Å	T = 120 K
β = 101.039 (3)º	Prism, colorless
V = 1231.13 (7) Å3	0.58 × 0.25 × 0.17 mm
Z = 4

Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector	2556 independent reflections
Radiation source: X-ray tube	1544 reflections with I > 3σ(I)
Monochromator: graphite	Rint = 0.054
Detector resolution: 8.3438 pixels mm-1	θmax = 26.5º
T = 120 K	θmin = 2.6º
Rotation method data acquisition using ω scans	h = −17→17
Absorption correction: none	k = −7→7
15703 measured reflections	l = −19→19

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	Extinction correction: none

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)

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) .