Ethyl 8-amino-6-bromoimidazo[1,2-a]pyridine-2-carb-oxy-late.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(10)H(10)BrN(3)O(2), which are linked by N-H⋯O and C-H⋯O hydrogen bonds. The fused ring systems in both mol-ecules are nearly planar with maximum deviations of 0.001 (3) and 0.029 (3) Å. All non-H atoms of the first mol-ecule are approximately co-planar whereas in the second mol-ecule, the ethyl group is almost perpendicular to the imidazo[1,2-a]pyridine system, the C-O-C-C torsion angles in the carb-oxy-lic acid ethyl group being -179.8 (4) and 112.1 (5)°, respectively.

Related literature

For the biological activity of imidazo[1,2-a]pyridine derivatives, see: Anderson et al. (2003 ▶); Trapani et al. (2003 ▶); Gueiffier et al. (1998 ▶); Mavel et al. (2002 ▶). For their pharmacological activity, see: Rival et al. (1992 ▶); Rupert et al. (2003 ▶); Katritzky et al. (2003 ▶).

Experimental

Crystal data

C10H10BrN3O2

M = 284.12

Monoclinic,

a = 8.366 (2) Å

b = 11.842 (3) Å

c = 22.743 (5) Å

β = 98.328 (6)°

V = 2229.3 (8) Å3

Z = 8

Mo Kα radiation

μ = 3.68 mm−1

T = 292 K

0.44 × 0.19 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.437, T max = 0.535

13222 measured reflections

4555 independent reflections

3156 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.116

S = 1.03

4555 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017077/dn2683sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017077/dn2683Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017077/dn2683Isup3.cml

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

C10H10BrN3O2	F(000) = 1136
Mr = 284.12	Dx = 1.693 Mg m−3
Monoclinic, P21/c	Melting point: 414(2) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.366 (2) Å	Cell parameters from 4555 reflections
b = 11.842 (3) Å	θ = 1.8–26.8°
c = 22.743 (5) Å	µ = 3.68 mm−1
β = 98.328 (6)°	T = 292 K
V = 2229.3 (8) Å3	Fiber, yellow
Z = 8	0.44 × 0.19 × 0.17 mm

Bruker APEXII CCD diffractometer	4555 independent reflections
Radiation source: fine-focus sealed tube	3156 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 26.8°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.437, Tmax = 0.535	k = −11→14
13222 measured reflections	l = −24→28

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0571P)2 + 1.0629P] where P = (Fo2 + 2Fc2)/3
4555 reflections	(Δ/σ)max = 0.001
291 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2σ(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
C1	0.6311 (4)	0.1790 (2)	0.24000 (15)	0.0364 (7)
C2	0.5137 (4)	0.1042 (3)	0.20858 (16)	0.0424 (8)
C3	0.3848 (4)	0.0737 (3)	0.23542 (17)	0.0463 (8)
H3	0.3073	0.0248	0.2162	0.056*
C4	0.3685 (4)	0.1156 (3)	0.29203 (17)	0.0457 (8)
C5	0.4772 (4)	0.1854 (3)	0.32284 (16)	0.0458 (8)
H5	0.4651	0.2114	0.3605	0.055*
C6	0.7346 (4)	0.2859 (3)	0.31519 (15)	0.0407 (7)
H6	0.7531	0.3244	0.3512	0.049*
C7	0.8290 (4)	0.2868 (3)	0.27069 (15)	0.0399 (7)
C8	0.9804 (4)	0.3528 (3)	0.27430 (17)	0.0442 (8)
C9	1.2055 (5)	0.4046 (4)	0.2303 (2)	0.0646 (11)
H9A	1.2805	0.3841	0.2653	0.078*
H9B	1.1815	0.4845	0.2327	0.078*
C10	1.2790 (6)	0.3820 (4)	0.1765 (2)	0.0738 (13)
H10A	1.3755	0.4263	0.1775	0.111*
H10B	1.2041	0.4018	0.1420	0.111*
H10C	1.3056	0.3033	0.1750	0.111*
N1	0.6074 (3)	0.2165 (2)	0.29548 (13)	0.0391 (6)
N2	0.7654 (3)	0.2206 (2)	0.22339 (12)	0.0387 (6)
N3	0.5421 (4)	0.0657 (3)	0.15447 (15)	0.0609 (9)
H3A	0.4634	0.0338	0.1320	0.073*
H3B	0.6048	0.1043	0.1351	0.073*
O1	1.0571 (3)	0.33902 (19)	0.22826 (11)	0.0493 (6)
O2	1.0266 (3)	0.4127 (2)	0.31636 (13)	0.0619 (7)
Br1	0.18490 (5)	0.07406 (4)	0.32785 (2)	0.06942 (17)
C11	0.8701 (4)	0.5979 (3)	0.45987 (15)	0.0382 (7)
C12	0.9608 (4)	0.6732 (3)	0.42770 (16)	0.0422 (8)
C13	1.0265 (4)	0.7670 (3)	0.45760 (17)	0.0472 (8)
H13	1.0798	0.8209	0.4379	0.057*
C14	1.0129 (4)	0.7813 (3)	0.51807 (17)	0.0450 (8)
C15	0.9362 (4)	0.7088 (3)	0.54986 (17)	0.0462 (8)
H15	0.9324	0.7195	0.5901	0.055*
C16	0.7710 (4)	0.5322 (3)	0.53803 (16)	0.0418 (8)
H16	0.7459	0.5214	0.5762	0.050*
C17	0.7243 (3)	0.4671 (3)	0.48894 (15)	0.0367 (7)
C18	0.6206 (4)	0.3662 (3)	0.48367 (16)	0.0432 (8)
C19	0.4773 (5)	0.2335 (4)	0.5359 (2)	0.0772 (14)
H19A	0.3926	0.2537	0.5590	0.093*
H19B	0.4272	0.2181	0.4956	0.093*
C20	0.5572 (7)	0.1346 (5)	0.5605 (4)	0.118 (2)
H20A	0.4790	0.0766	0.5638	0.177*
H20B	0.6147	0.1514	0.5991	0.177*
H20C	0.6320	0.1091	0.5351	0.177*
N4	0.8630 (3)	0.6170 (2)	0.51890 (13)	0.0399 (6)
N5	0.7852 (3)	0.5068 (2)	0.43990 (12)	0.0400 (6)
N6	0.9732 (4)	0.6470 (3)	0.37068 (14)	0.0565 (8)
H6A	1.0318	0.6877	0.3512	0.068*
H6B	0.9494	0.5790	0.3605	0.068*
O3	0.5891 (3)	0.3286 (2)	0.53566 (12)	0.0551 (6)
O4	0.5670 (3)	0.3250 (3)	0.43682 (13)	0.0718 (8)
Br2	1.11787 (5)	0.90661 (3)	0.55921 (2)	0.06673 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0447 (17)	0.0342 (16)	0.0290 (19)	0.0055 (13)	0.0002 (13)	−0.0018 (13)
C2	0.0483 (19)	0.0406 (18)	0.036 (2)	0.0027 (14)	−0.0025 (15)	−0.0035 (14)
C3	0.0489 (19)	0.0436 (19)	0.043 (2)	−0.0036 (14)	−0.0038 (15)	−0.0022 (15)
C4	0.0421 (18)	0.0477 (19)	0.048 (2)	−0.0002 (14)	0.0078 (15)	−0.0012 (16)
C5	0.0481 (19)	0.052 (2)	0.039 (2)	−0.0039 (15)	0.0119 (15)	−0.0082 (16)
C6	0.0470 (18)	0.0433 (18)	0.032 (2)	−0.0051 (14)	0.0057 (14)	−0.0103 (14)
C7	0.0445 (18)	0.0396 (17)	0.035 (2)	0.0010 (13)	0.0038 (14)	−0.0032 (14)
C8	0.050 (2)	0.0431 (19)	0.039 (2)	0.0005 (15)	0.0071 (15)	−0.0031 (15)
C9	0.050 (2)	0.071 (3)	0.075 (3)	−0.0188 (18)	0.015 (2)	−0.014 (2)
C10	0.073 (3)	0.076 (3)	0.076 (4)	−0.017 (2)	0.022 (2)	0.002 (2)
N1	0.0401 (14)	0.0400 (14)	0.0370 (18)	0.0004 (11)	0.0050 (11)	−0.0060 (12)
N2	0.0459 (15)	0.0400 (14)	0.0299 (16)	0.0022 (11)	0.0046 (11)	−0.0048 (11)
N3	0.071 (2)	0.074 (2)	0.036 (2)	−0.0150 (16)	0.0027 (15)	−0.0158 (15)
O1	0.0495 (13)	0.0516 (14)	0.0492 (17)	−0.0087 (10)	0.0148 (11)	−0.0136 (11)
O2	0.0700 (17)	0.0704 (18)	0.0464 (18)	−0.0226 (13)	0.0126 (13)	−0.0225 (14)
Br1	0.0567 (3)	0.0777 (3)	0.0779 (4)	−0.01732 (19)	0.0233 (2)	−0.0092 (2)
C11	0.0426 (17)	0.0423 (17)	0.0292 (19)	0.0124 (14)	0.0030 (13)	0.0034 (14)
C12	0.0444 (18)	0.0447 (19)	0.037 (2)	0.0086 (14)	0.0035 (14)	0.0056 (15)
C13	0.052 (2)	0.0419 (19)	0.048 (2)	0.0031 (15)	0.0075 (16)	0.0079 (16)
C14	0.0484 (19)	0.0375 (17)	0.047 (2)	0.0041 (14)	−0.0003 (15)	−0.0022 (15)
C15	0.056 (2)	0.0454 (19)	0.035 (2)	0.0031 (15)	0.0003 (15)	−0.0051 (15)
C16	0.0446 (18)	0.0478 (19)	0.033 (2)	0.0039 (14)	0.0062 (14)	0.0050 (15)
C17	0.0349 (15)	0.0437 (17)	0.032 (2)	0.0073 (13)	0.0047 (13)	−0.0007 (14)
C18	0.0396 (17)	0.0526 (19)	0.038 (2)	0.0056 (14)	0.0075 (15)	−0.0054 (16)
C19	0.067 (3)	0.074 (3)	0.089 (4)	−0.018 (2)	0.006 (2)	0.017 (3)
C20	0.096 (4)	0.076 (4)	0.183 (8)	−0.014 (3)	0.026 (4)	0.027 (4)
N4	0.0433 (15)	0.0402 (15)	0.0352 (18)	0.0041 (11)	0.0024 (12)	−0.0005 (11)
N5	0.0412 (14)	0.0463 (15)	0.0318 (17)	0.0057 (12)	0.0029 (11)	0.0002 (12)
N6	0.081 (2)	0.0522 (18)	0.039 (2)	−0.0051 (15)	0.0172 (15)	0.0063 (14)
O3	0.0587 (15)	0.0573 (15)	0.0489 (18)	−0.0115 (12)	0.0064 (12)	0.0049 (12)
O4	0.0805 (19)	0.088 (2)	0.049 (2)	−0.0289 (16)	0.0165 (14)	−0.0289 (15)
Br2	0.0787 (3)	0.0502 (2)	0.0698 (3)	−0.01168 (19)	0.0056 (2)	−0.01129 (19)

C1—N2	1.331 (4)	C11—N5	1.335 (4)
C1—N1	1.379 (4)	C11—N4	1.371 (4)
C1—C2	1.434 (4)	C11—C12	1.437 (5)
C2—C3	1.363 (5)	C12—N6	1.352 (4)
C2—N3	1.365 (5)	C12—C13	1.376 (5)
C3—C4	1.405 (5)	C13—C14	1.407 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.348 (5)	C14—C15	1.344 (5)
C4—Br1	1.904 (3)	C14—Br2	1.900 (3)
C5—N1	1.380 (4)	C15—N4	1.389 (4)
C5—H5	0.9300	C15—H15	0.9300
C6—N1	1.368 (4)	C16—C17	1.367 (5)
C6—C7	1.371 (5)	C16—N4	1.374 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—N2	1.374 (4)	C17—N5	1.375 (4)
C7—C8	1.480 (5)	C17—C18	1.472 (5)
C8—O2	1.209 (4)	C18—O4	1.199 (4)
C8—O1	1.315 (4)	C18—O3	1.325 (4)
C9—O1	1.460 (4)	C19—C20	1.422 (7)
C9—C10	1.471 (6)	C19—O3	1.464 (5)
C9—H9A	0.9700	C19—H19A	0.9700
C9—H9B	0.9700	C19—H19B	0.9700
C10—H10A	0.9600	C20—H20A	0.9600
C10—H10B	0.9600	C20—H20B	0.9600
C10—H10C	0.9600	C20—H20C	0.9600
N3—H3A	0.8604	N6—H6A	0.8550
N3—H3B	0.8634	N6—H6B	0.8530
N2—C1—N1	112.3 (3)	N5—C11—N4	111.7 (3)
N2—C1—C2	129.3 (3)	N5—C11—C12	128.5 (3)
N1—C1—C2	118.4 (3)	N4—C11—C12	119.8 (3)
C3—C2—N3	124.6 (3)	N6—C12—C13	125.3 (3)
C3—C2—C1	118.0 (3)	N6—C12—C11	117.8 (3)
N3—C2—C1	117.3 (3)	C13—C12—C11	116.9 (3)
C2—C3—C4	120.3 (3)	C12—C13—C14	119.8 (3)
C2—C3—H3	119.8	C12—C13—H13	120.1
C4—C3—H3	119.8	C14—C13—H13	120.1
C5—C4—C3	123.1 (3)	C15—C14—C13	124.2 (3)
C5—C4—Br1	117.5 (3)	C15—C14—Br2	117.1 (3)
C3—C4—Br1	119.5 (3)	C13—C14—Br2	118.6 (3)
C4—C5—N1	116.5 (3)	C14—C15—N4	115.9 (3)
C4—C5—H5	121.7	C14—C15—H15	122.0
N1—C5—H5	121.7	N4—C15—H15	122.0
N1—C6—C7	105.5 (3)	C17—C16—N4	105.1 (3)
N1—C6—H6	127.3	C17—C16—H16	127.4
C7—C6—H6	127.3	N4—C16—H16	127.4
C6—C7—N2	112.0 (3)	C16—C17—N5	112.0 (3)
C6—C7—C8	122.9 (3)	C16—C17—C18	128.3 (3)
N2—C7—C8	125.1 (3)	N5—C17—C18	119.7 (3)
O2—C8—O1	124.4 (3)	O4—C18—O3	124.0 (3)
O2—C8—C7	121.8 (3)	O4—C18—C17	122.9 (3)
O1—C8—C7	113.8 (3)	O3—C18—C17	113.0 (3)
O1—C9—C10	109.4 (3)	C20—C19—O3	111.7 (4)
O1—C9—H9A	109.8	C20—C19—H19A	109.3
C10—C9—H9A	109.8	O3—C19—H19A	109.3
O1—C9—H9B	109.8	C20—C19—H19B	109.3
C10—C9—H9B	109.8	O3—C19—H19B	109.3
H9A—C9—H9B	108.2	H19A—C19—H19B	107.9
C9—C10—H10A	109.5	C19—C20—H20A	109.5
C9—C10—H10B	109.5	C19—C20—H20B	109.5
H10A—C10—H10B	109.5	H20A—C20—H20B	109.5
C9—C10—H10C	109.5	C19—C20—H20C	109.5
H10A—C10—H10C	109.5	H20A—C20—H20C	109.5
H10B—C10—H10C	109.5	H20B—C20—H20C	109.5
C6—N1—C1	106.6 (3)	C11—N4—C16	107.2 (3)
C6—N1—C5	129.8 (3)	C11—N4—C15	123.2 (3)
C1—N1—C5	123.7 (3)	C16—N4—C15	129.6 (3)
C1—N2—C7	103.7 (3)	C11—N5—C17	104.0 (3)
C2—N3—H3A	117.6	C12—N6—H6A	119.8
C2—N3—H3B	118.9	C12—N6—H6B	115.4
H3A—N3—H3B	113.5	H6A—N6—H6B	121.3
C8—O1—C9	114.8 (3)	C18—O3—C19	118.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N5i	0.86	2.47	3.300 (4)	161
N3—H3B···O3ii	0.86	2.38	3.055 (5)	135
N6—H6B···O2	0.85	2.34	3.096 (4)	147
N6—H6A···O1iii	0.86	2.58	3.183 (4)	129
N6—H6A···N2iii	0.86	2.60	3.388 (4)	154
C5—H5···O4	0.93	2.26	3.074 (4)	146
C19—H19B···O4	0.97	2.28	2.703 (6)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N5i	0.86	2.47	3.300 (4)	161
N3—H3B⋯O3ii	0.86	2.38	3.055 (5)	135
N6—H6B⋯O2	0.85	2.34	3.096 (4)	147
N6—H6A⋯O1iii	0.86	2.58	3.183 (4)	129
N6—H6A⋯N2iii	0.86	2.60	3.388 (4)	154
C5—H5⋯O4	0.93	2.26	3.074 (4)	146

Symmetry codes: (i) ; (ii) ; (iii) .