1,3-Diallyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one.

In the mol-ecule of the title compound, C(12)H(12)BrN(3)O, the fused-ring system is essentially planar, the largest deviation from the mean plane being 0.0148 (3) Å. The two allyl groups are nearly perpendicular to the imidazo[4,5-b]pyridine plane [C-C-N-C torsion angles of 81.6 (4) and -77.2 (4)°] and point in the same direction. The planes through the atoms forming each allyl group are nearly perpendicular to the imidazo[4,5-b]pyridin-2-one system, as indicated by the dihedral angles between them of 80.8 (5) and 73.6 (5)°.

Related literature

For background to the biological activity of substituted imidazopyridines and related compounds, see: Barraclough et al. (1990 ▶); Bavetsias et al. (2007 ▶, 2010 ▶); Coates et al. (1993 ▶); Liu et al. (2008 ▶); Ryabukhin et al. (2006 ▶); Schiffmann et al. (2006 ▶).

Experimental

Crystal data

C12H12BrN3O

M = 294.16

Orthorhombic,

a = 5.4110 (3) Å

b = 25.4205 (12) Å

c = 9.3170 (4) Å

V = 1281.56 (11) Å3

Z = 4

Mo Kα radiation

μ = 3.20 mm−1

T = 273 K

0.52 × 0.32 × 0.14 mm

Data collection

Bruker CCD three-circle diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.202, T max = 0.800

8789 measured reflections

3201 independent reflections

2361 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.03

3201 reflections

156 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983) ▶, 1494 Friedel pairs

Flack parameter: 0.040 (17)

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811026869/om2445sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026869/om2445Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026869/om2445Isup3.cml

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

C12H12BrN3O	F(000) = 592
Mr = 294.16	Dx = 1.525 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2c -2n	Cell parameters from 3201 reflections
a = 5.4110 (3) Å	θ = 1.6–28.5°
b = 25.4205 (12) Å	µ = 3.20 mm−1
c = 9.3170 (4) Å	T = 273 K
V = 1281.56 (11) Å3	Block, colourless
Z = 4	0.52 × 0.32 × 0.14 mm

Bruker CCD three-circle diffractometer	3201 independent reflections
Radiation source: sealed tube	2361 reflections with I > 2σ(I)
graphite	Rint = 0.027
phi and ω scans	θmax = 28.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −6→7
Tmin = 0.202, Tmax = 0.800	k = −25→34
8789 measured reflections	l = −12→12

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0402P)2 + 0.2176P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3201 reflections	Δρmax = 0.44 e Å−3
156 parameters	Δρmin = −0.23 e Å−3
1 restraint	Absolute structure: Flack (1983), 1494 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.040 (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 Rw factor 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
Br1	0.99838 (6)	0.148410 (15)	0.99886 (11)	0.07396 (14)
N1	0.5607 (5)	0.19539 (10)	0.6617 (3)	0.0585 (6)
N2	0.2257 (4)	0.14754 (9)	0.5520 (3)	0.0541 (6)
N3	0.2480 (5)	0.07428 (9)	0.6813 (3)	0.0552 (6)
O1	−0.0599 (4)	0.08103 (10)	0.5080 (4)	0.0730 (6)
C1	0.7552 (5)	0.14820 (11)	0.8523 (3)	0.0515 (7)
C2	0.7283 (6)	0.19139 (12)	0.7678 (4)	0.0592 (8)
H2	0.8321	0.2199	0.7842	0.071*
C3	0.6043 (6)	0.10361 (12)	0.8374 (3)	0.0532 (7)
H3	0.6209	0.0739	0.8948	0.064*
C4	0.4298 (5)	0.10753 (12)	0.7306 (3)	0.0496 (6)
C5	0.4169 (6)	0.15329 (11)	0.6493 (4)	0.0489 (6)
C6	0.1188 (6)	0.09843 (13)	0.5717 (4)	0.0579 (7)
C7	0.1361 (6)	0.18683 (13)	0.4530 (4)	0.0621 (8)
H7A	0.1349	0.2207	0.5011	0.075*
H7B	−0.0331	0.1784	0.4274	0.075*
C8	0.2846 (7)	0.19138 (15)	0.3195 (4)	0.0706 (9)
H8	0.2371	0.2173	0.2548	0.090 (12)*
C9	0.4653 (9)	0.1641 (3)	0.2855 (6)	0.0939 (15)
H9A	0.5201	0.1376	0.3466	0.113*
H9B	0.5461	0.1701	0.1989	0.113*
C10	0.1712 (7)	0.02523 (13)	0.7497 (4)	0.0694 (9)
H10A	0.0091	0.0156	0.7137	0.083*
H10B	0.1562	0.0311	0.8522	0.083*
C11	0.3410 (8)	−0.01892 (15)	0.7256 (5)	0.0771 (10)
H11	0.3027	−0.0503	0.7717	0.129 (19)*
C12	0.5362 (7)	−0.01882 (17)	0.6479 (6)	0.0832 (12)
H12A	0.5828	0.0116	0.5995	0.100*
H12B	0.6313	−0.0491	0.6400	0.100*

	U11	U22	U33	U12	U13	U23
Br1	0.05433 (18)	0.1026 (3)	0.0649 (2)	0.00262 (14)	−0.01189 (13)	−0.0127 (2)
N1	0.0564 (13)	0.0460 (14)	0.0731 (17)	−0.0070 (11)	−0.0083 (14)	0.0032 (13)
N2	0.0478 (13)	0.0545 (14)	0.0599 (15)	−0.0015 (10)	−0.0090 (11)	0.0029 (10)
N3	0.0493 (13)	0.0476 (13)	0.0686 (15)	−0.0089 (10)	−0.0042 (12)	0.0025 (11)
O1	0.0564 (12)	0.0847 (15)	0.0781 (16)	−0.0178 (10)	−0.0148 (16)	−0.0040 (16)
C1	0.0412 (14)	0.0642 (18)	0.0489 (15)	0.0007 (13)	−0.0024 (12)	−0.0096 (13)
C2	0.0507 (16)	0.0556 (17)	0.071 (2)	−0.0074 (13)	−0.0041 (15)	−0.0080 (15)
C3	0.0489 (15)	0.0567 (17)	0.0539 (16)	0.0026 (13)	0.0034 (14)	0.0046 (13)
C4	0.0416 (14)	0.0549 (17)	0.0522 (16)	−0.0013 (11)	0.0038 (12)	−0.0024 (13)
C5	0.0446 (14)	0.0454 (16)	0.0566 (17)	0.0003 (11)	−0.0005 (14)	−0.0055 (13)
C6	0.0531 (17)	0.0630 (18)	0.0575 (17)	−0.0051 (14)	−0.0016 (15)	−0.0051 (15)
C7	0.0550 (17)	0.0651 (19)	0.0662 (19)	0.0019 (13)	−0.0108 (15)	0.0016 (15)
C8	0.077 (2)	0.083 (2)	0.0523 (17)	−0.0094 (19)	−0.0090 (18)	0.0031 (17)
C9	0.092 (4)	0.119 (4)	0.071 (3)	0.003 (2)	0.017 (2)	−0.005 (3)
C10	0.065 (2)	0.062 (2)	0.081 (2)	−0.0164 (15)	0.0003 (19)	0.0097 (17)
C11	0.089 (3)	0.056 (2)	0.086 (3)	−0.0155 (18)	0.004 (2)	0.0058 (18)
C12	0.086 (3)	0.066 (3)	0.098 (3)	−0.0118 (17)	0.008 (2)	−0.014 (2)

Br1—C1	1.896 (3)	C4—C5	1.390 (4)
N1—C5	1.328 (4)	C7—C8	1.485 (5)
N1—C2	1.345 (4)	C7—H7A	0.9700
N2—C5	1.383 (4)	C7—H7B	0.9700
N2—C6	1.388 (4)	C8—C9	1.240 (6)
N2—C7	1.444 (4)	C8—H8	0.9300
N3—C4	1.376 (4)	C9—H9A	0.9300
N3—C6	1.381 (4)	C9—H9B	0.9300
N3—C10	1.461 (4)	C10—C11	1.467 (6)
O1—C6	1.218 (4)	C10—H10A	0.9700
C1—C2	1.359 (4)	C10—H10B	0.9700
C1—C3	1.404 (4)	C11—C12	1.281 (6)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.375 (5)	C12—H12A	0.9300
C3—H3	0.9300	C12—H12B	0.9300
C5—N1—C2	113.5 (3)	N2—C7—C8	114.0 (3)
C5—N2—C6	108.7 (2)	N2—C7—H7A	108.7
C5—N2—C7	126.6 (2)	C8—C7—H7A	108.7
C6—N2—C7	124.5 (3)	N2—C7—H7B	108.7
C4—N3—C6	109.6 (3)	C8—C7—H7B	108.7
C4—N3—C10	125.6 (3)	H7A—C7—H7B	107.6
C6—N3—C10	123.9 (3)	C9—C8—C7	126.6 (4)
C2—C1—C3	122.2 (3)	C9—C8—H8	116.7
C2—C1—Br1	119.3 (2)	C7—C8—H8	116.7
C3—C1—Br1	118.5 (2)	C8—C9—H9A	120.0
N1—C2—C1	124.0 (3)	C8—C9—H9B	120.0
N1—C2—H2	118.0	H9A—C9—H9B	120.0
C1—C2—H2	118.0	N3—C10—C11	114.1 (3)
C4—C3—C1	114.4 (3)	N3—C10—H10A	108.7
C4—C3—H3	122.8	C11—C10—H10A	108.7
C1—C3—H3	122.8	N3—C10—H10B	108.7
C3—C4—N3	133.4 (3)	C11—C10—H10B	108.7
C3—C4—C5	119.3 (3)	H10A—C10—H10B	107.6
N3—C4—C5	107.3 (3)	C12—C11—C10	127.0 (4)
N1—C5—N2	125.5 (3)	C12—C11—H11	116.5
N1—C5—C4	126.7 (3)	C10—C11—H11	116.5
N2—C5—C4	107.8 (2)	C11—C12—H12A	120.0
O1—C6—N3	126.9 (3)	C11—C12—H12B	120.0
O1—C6—N2	126.4 (3)	H12A—C12—H12B	120.0
N3—C6—N2	106.6 (3)
C5—N1—C2—C1	1.8 (5)	N3—C4—C5—N1	−179.7 (3)
C3—C1—C2—N1	−1.2 (5)	C3—C4—C5—N2	−179.1 (3)
Br1—C1—C2—N1	−179.5 (3)	N3—C4—C5—N2	0.5 (3)
C2—C1—C3—C4	0.2 (4)	C4—N3—C6—O1	−176.8 (4)
Br1—C1—C3—C4	178.6 (2)	C10—N3—C6—O1	−7.0 (5)
C1—C3—C4—N3	−179.4 (3)	C4—N3—C6—N2	0.7 (3)
C1—C3—C4—C5	0.0 (4)	C10—N3—C6—N2	170.5 (3)
C6—N3—C4—C3	178.7 (3)	C5—N2—C6—O1	177.2 (4)
C10—N3—C4—C3	9.2 (6)	C7—N2—C6—O1	1.4 (5)
C6—N3—C4—C5	−0.7 (3)	C5—N2—C6—N3	−0.4 (3)
C10—N3—C4—C5	−170.3 (3)	C7—N2—C6—N3	−176.1 (3)
C2—N1—C5—N2	178.2 (3)	C5—N2—C7—C8	81.6 (4)
C2—N1—C5—C4	−1.6 (5)	C6—N2—C7—C8	−103.5 (3)
C6—N2—C5—N1	−179.9 (3)	N2—C7—C8—C9	2.7 (6)
C7—N2—C5—N1	−4.3 (5)	C4—N3—C10—C11	−77.2 (4)
C6—N2—C5—C4	−0.1 (3)	C6—N3—C10—C11	114.7 (4)
C7—N2—C5—C4	175.5 (3)	N3—C10—C11—C12	−3.3 (6)
C3—C4—C5—N1	0.8 (5)