Ethyl 5-methyl-imidazo[1,2-a]pyridine-2-carboxyl-ate.

The title compound, C(11)H(12)N(2)O(2), was synthesized from the reaction of 6-methyl-pyridin-2-amine and ethyl 3-bromo-2-oxopropionate. In the mol-ecular structure, the six- and five-membered rings are individually almost planar with r.m.s. deviations of 0.003 and 0.002 Å, respectively. The two rings are almost coplanar, the dihedral angle between their planes being 1.4 (3)°. Inter-molecular C-H⋯O and C-H⋯N hydrogen bonds are present in the crystal structure.

Related literature

For the biological properties of related compounds, see: Xia et al. (2005 ▶); Warshakoon et al. (2006 ▶); Imaeda et al. (2008 ▶). For the synthetic procedure, see: Xia et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H12N2O2

M = 204.23

Monoclinic,

a = 17.164 (3) Å

b = 10.521 (2) Å

c = 13.759 (3) Å

β = 124.77 (3)°

V = 2041 (1) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.973, T max = 0.991

1923 measured reflections

1859 independent reflections

1360 reflections with I > 2σ(I)

R int = 0.028

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.152

S = 1.00

1859 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026577/im2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026577/im2214Isup2.hkl

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

C11H12N2O2	F(000) = 864
Mr = 204.23	Dx = 1.329 Mg m−3
Monoclinic, C2/c	Melting point = 425–426 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 17.164 (3) Å	Cell parameters from 25 reflections
b = 10.521 (2) Å	θ = 9–13°
c = 13.759 (3) Å	µ = 0.09 mm−1
β = 124.77 (3)°	T = 293 K
V = 2041 (1) Å3	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1360 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 25.3°, θmin = 2.4°
ω/2θ scans	h = −20→0
Absorption correction: ψ scan (North et al., 1968)	k = −12→0
Tmin = 0.973, Tmax = 0.991	l = −13→16
1923 measured reflections	3 standard reflections every 200 reflections
1859 independent reflections	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1859 reflections	Δρmax = 0.24 e Å−3
137 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0117 (17)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.12866 (11)	0.40243 (18)	0.19751 (15)	0.0466 (5)
O1	0.07064 (11)	0.13738 (15)	0.15389 (15)	0.0602 (5)
C1	0.06679 (17)	0.7803 (2)	0.15626 (19)	0.0523 (6)
H1B	0.0502	0.8658	0.1452	0.063*
N2	0.02673 (11)	0.56505 (15)	0.13920 (13)	0.0376 (4)
O2	−0.07427 (10)	0.20448 (14)	0.09371 (13)	0.0512 (5)
C2	0.16246 (17)	0.7466 (3)	0.2109 (2)	0.0582 (6)
H2A	0.2075	0.8102	0.2346	0.070*
C3	0.19016 (14)	0.6232 (2)	0.22978 (18)	0.0527 (6)
H3A	0.2537	0.6020	0.2665	0.063*
C4	0.12108 (13)	0.5273 (2)	0.19286 (17)	0.0422 (5)
C5	0.03813 (14)	0.3590 (2)	0.14702 (17)	0.0408 (5)
C6	−0.02457 (13)	0.45553 (19)	0.11134 (16)	0.0387 (5)
H6A	−0.0896	0.4487	0.0751	0.046*
C7	−0.00174 (15)	0.6916 (2)	0.11927 (17)	0.0432 (5)
C8	−0.10473 (15)	0.7154 (2)	0.05724 (19)	0.0509 (6)
H8A	−0.1164	0.8053	0.0480	0.076*
H8B	−0.1260	0.6807	0.1028	0.076*
H8C	−0.1385	0.6757	−0.0192	0.076*
C9	0.01645 (14)	0.2218 (2)	0.13352 (17)	0.0432 (5)
C10	−0.10735 (16)	0.0748 (2)	0.0699 (2)	0.0560 (6)
H10A	−0.0701	0.0241	0.1412	0.067*
H10B	−0.1011	0.0386	0.0098	0.067*
C11	−0.20816 (17)	0.0755 (3)	0.0283 (2)	0.0727 (8)
H11A	−0.2321	−0.0099	0.0114	0.109*
H11B	−0.2443	0.1261	−0.0421	0.109*
H11C	−0.2134	0.1109	0.0887	0.109*

	U11	U22	U33	U12	U13	U23
N1	0.0347 (9)	0.0568 (12)	0.0450 (10)	0.0026 (8)	0.0208 (8)	0.0007 (8)
O1	0.0514 (10)	0.0524 (10)	0.0734 (11)	0.0127 (8)	0.0335 (9)	0.0054 (8)
C1	0.0589 (14)	0.0472 (13)	0.0525 (13)	−0.0098 (11)	0.0328 (11)	−0.0024 (10)
N2	0.0335 (9)	0.0460 (10)	0.0347 (9)	−0.0019 (7)	0.0202 (7)	−0.0025 (7)
O2	0.0443 (9)	0.0417 (9)	0.0654 (10)	−0.0026 (6)	0.0301 (8)	−0.0048 (7)
C2	0.0540 (14)	0.0666 (16)	0.0554 (13)	−0.0196 (12)	0.0320 (11)	−0.0058 (12)
C3	0.0362 (11)	0.0717 (17)	0.0488 (13)	−0.0106 (10)	0.0234 (10)	−0.0027 (11)
C4	0.0330 (10)	0.0564 (14)	0.0360 (10)	−0.0003 (9)	0.0188 (8)	−0.0004 (9)
C5	0.0365 (10)	0.0492 (12)	0.0365 (10)	0.0012 (9)	0.0207 (9)	0.0003 (9)
C6	0.0327 (10)	0.0457 (12)	0.0372 (10)	−0.0037 (9)	0.0196 (8)	−0.0020 (9)
C7	0.0474 (12)	0.0466 (13)	0.0387 (11)	−0.0031 (10)	0.0264 (9)	−0.0024 (9)
C8	0.0498 (13)	0.0447 (13)	0.0588 (13)	0.0022 (10)	0.0313 (11)	−0.0019 (10)
C9	0.0397 (11)	0.0491 (13)	0.0401 (11)	0.0056 (9)	0.0223 (9)	0.0022 (9)
C10	0.0557 (14)	0.0427 (13)	0.0662 (15)	−0.0034 (10)	0.0327 (12)	−0.0038 (11)
C11	0.0557 (15)	0.0608 (17)	0.092 (2)	−0.0087 (12)	0.0369 (15)	−0.0109 (14)

N1—C4	1.318 (3)	C3—H3A	0.9300
N1—C5	1.369 (2)	C5—C6	1.352 (3)
O1—C9	1.198 (2)	C5—C9	1.475 (3)
C1—C7	1.353 (3)	C6—H6A	0.9300
C1—C2	1.407 (3)	C7—C8	1.482 (3)
C1—H1B	0.9300	C8—H8A	0.9600
N2—C6	1.366 (2)	C8—H8B	0.9600
N2—C7	1.391 (3)	C8—H8C	0.9600
N2—C4	1.401 (2)	C10—C11	1.480 (3)
O2—C9	1.336 (2)	C10—H10A	0.9700
O2—C10	1.442 (3)	C10—H10B	0.9700
C2—C3	1.357 (4)	C11—H11A	0.9600
C2—H2A	0.9300	C11—H11B	0.9600
C3—C4	1.412 (3)	C11—H11C	0.9600
C4—N1—C5	104.84 (16)	C1—C7—C8	126.6 (2)
C7—C1—C2	121.8 (2)	N2—C7—C8	116.43 (18)
C7—C1—H1B	119.1	C7—C8—H8A	109.5
C2—C1—H1B	119.1	C7—C8—H8B	109.5
C6—N2—C7	130.90 (17)	H8A—C8—H8B	109.5
C6—N2—C4	105.97 (16)	C7—C8—H8C	109.5
C7—N2—C4	123.11 (16)	H8A—C8—H8C	109.5
C9—O2—C10	116.01 (17)	H8B—C8—H8C	109.5
C3—C2—C1	121.2 (2)	O1—C9—O2	124.2 (2)
C3—C2—H2A	119.4	O1—C9—C5	126.1 (2)
C1—C2—H2A	119.4	O2—C9—C5	109.67 (17)
C2—C3—C4	119.0 (2)	O2—C10—C11	107.8 (2)
C2—C3—H3A	120.5	O2—C10—H10A	110.2
C4—C3—H3A	120.5	C11—C10—H10A	110.2
N1—C4—N2	111.15 (17)	O2—C10—H10B	110.2
N1—C4—C3	130.93 (19)	C11—C10—H10B	110.2
N2—C4—C3	117.91 (19)	H10A—C10—H10B	108.5
C6—C5—N1	111.79 (19)	C10—C11—H11A	109.5
C6—C5—C9	126.71 (19)	C10—C11—H11B	109.5
N1—C5—C9	121.48 (18)	H11A—C11—H11B	109.5
C5—C6—N2	106.24 (17)	C10—C11—H11C	109.5
C5—C6—H6A	126.9	H11A—C11—H11C	109.5
N2—C6—H6A	126.9	H11B—C11—H11C	109.5
C1—C7—N2	117.0 (2)
C7—C1—C2—C3	−0.6 (3)	C4—N2—C6—C5	−0.42 (19)
C1—C2—C3—C4	0.4 (3)	C2—C1—C7—N2	0.9 (3)
C5—N1—C4—N2	−0.5 (2)	C2—C1—C7—C8	−177.8 (2)
C5—N1—C4—C3	−179.0 (2)	C6—N2—C7—C1	−178.96 (19)
C6—N2—C4—N1	0.6 (2)	C4—N2—C7—C1	−1.2 (3)
C7—N2—C4—N1	−177.71 (17)	C6—N2—C7—C8	−0.2 (3)
C6—N2—C4—C3	179.30 (17)	C4—N2—C7—C8	177.64 (16)
C7—N2—C4—C3	1.0 (3)	C10—O2—C9—O1	−2.8 (3)
C2—C3—C4—N1	177.8 (2)	C10—O2—C9—C5	176.75 (17)
C2—C3—C4—N2	−0.6 (3)	C6—C5—C9—O1	171.5 (2)
C4—N1—C5—C6	0.2 (2)	N1—C5—C9—O1	−6.9 (3)
C4—N1—C5—C9	178.87 (19)	C6—C5—C9—O2	−8.0 (3)
N1—C5—C6—N2	0.2 (2)	N1—C5—C9—O2	173.49 (16)
C9—C5—C6—N2	−178.43 (18)	C9—O2—C10—C11	179.40 (18)
C7—N2—C6—C5	177.67 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N1i	0.93	2.59	3.461 (4)	155
C3—H3A···O1i	0.93	2.58	3.456 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯N1i	0.93	2.59	3.461 (4)	155
C3—H3A⋯O1i	0.93	2.58	3.456 (4)	157

Symmetry code: (i) .