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

The fused imidazole and pyridine rings in the title compound, C13H10BrN3O, are linked to a benzyl group. The fused ring system is essentially planar, the largest deviation from the mean plane being 0.006 (2) Å. The phenyl ring is not coplanar with the fused ring system, as indicated by the dihedral angle of 67.04 (12)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For the biological activity of imidazo­pyridine derivatives, see: Chen & Dost (1992 ▶); Cappelli et al. (2006 ▶); Weier et al. (1994 ▶); Kulkarni & Newman (2007 ▶); Bavetsias et al. (2007 ▶, 2010 ▶).

Experimental

Crystal data

C13H10BrN3O

M = 304.15

Triclinic,

a = 4.2399 (2) Å

b = 10.4463 (4) Å

c = 14.5144 (6) Å

α = 107.611 (2)°

β = 90.628 (3)°

γ = 99.784 (3)°

V = 602.49 (4) Å3

Z = 2

Mo Kα radiation

μ = 3.40 mm−1

T = 296 K

0.26 × 0.19 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.472, T max = 0.935

13819 measured reflections

2772 independent reflections

2169 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.085

S = 1.06

2772 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.55 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, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013780/fj2630sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013780/fj2630Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013780/fj2630Isup3.cml

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

C13H10BrN3O	Z = 2
Mr = 304.15	F(000) = 304
Triclinic, P1	Dx = 1.677 Mg m−3
Hall symbol: -P 1	Melting point: 358 K
a = 4.2399 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4463 (4) Å	Cell parameters from 2772 reflections
c = 14.5144 (6) Å	θ = 1.5–27.5°
α = 107.611 (2)°	µ = 3.40 mm−1
β = 90.628 (3)°	T = 296 K
γ = 99.784 (3)°	Platelet, colourless
V = 602.49 (4) Å3	0.26 × 0.19 × 0.02 mm

Bruker APEXII CCD diffractometer	2772 independent reflections
Radiation source: microfocus source	2169 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
Tmin = 0.472, Tmax = 0.935	k = −13→13
13819 measured reflections	l = −18→18

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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F2) = 0.085	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0374P)2 + 0.3201P] where P = (Fo2 + 2Fc2)/3
2772 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

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
Br1	0.26054 (8)	0.40434 (3)	0.14153 (2)	0.06526 (14)
C1	0.6829 (7)	0.6528 (3)	0.2362 (2)	0.0522 (7)
H1	0.7269	0.6048	0.2779	0.063*
C2	0.4658 (7)	0.5871 (3)	0.15899 (19)	0.0463 (6)
C3	0.3894 (6)	0.6511 (3)	0.09261 (18)	0.0448 (6)
H3	0.2437	0.6073	0.0395	0.054*
C4	0.5450 (6)	0.7837 (2)	0.11128 (16)	0.0373 (5)
C5	0.7610 (6)	0.8423 (2)	0.19198 (16)	0.0379 (5)
C6	0.7491 (6)	0.9986 (2)	0.11485 (16)	0.0387 (5)
C7	1.1131 (6)	1.0750 (3)	0.26618 (18)	0.0433 (6)
H7A	1.2362	1.1371	0.2363	0.052*
H7B	1.2615	1.0289	0.2896	0.052*
C8	0.9545 (5)	1.1565 (2)	0.35104 (16)	0.0381 (5)
C9	0.8773 (7)	1.2797 (3)	0.3530 (2)	0.0503 (6)
H9	0.9188	1.3126	0.3008	0.060*
C10	0.7386 (8)	1.3551 (3)	0.4320 (2)	0.0644 (8)
H10	0.6870	1.4385	0.4327	0.077*
C11	0.6766 (8)	1.3071 (4)	0.5096 (2)	0.0647 (8)
H11	0.5865	1.3586	0.5632	0.078*
C12	0.7474 (8)	1.1844 (4)	0.5076 (2)	0.0656 (8)
H12	0.7029	1.1513	0.5596	0.079*
C13	0.8849 (7)	1.1088 (3)	0.42872 (19)	0.0536 (7)
H13	0.9313	1.0245	0.4278	0.064*
N1	0.8370 (6)	0.7832 (2)	0.25554 (15)	0.0479 (5)
N2	0.8850 (5)	0.9739 (2)	0.19325 (14)	0.0385 (4)
N3	0.5415 (5)	0.8819 (2)	0.06533 (14)	0.0412 (5)
H14	0.4262	0.8712	0.0135	0.049*
O1	0.8058 (5)	1.10622 (18)	0.09525 (13)	0.0507 (4)

	U11	U22	U33	U12	U13	U23
Br1	0.0925 (3)	0.04191 (17)	0.0673 (2)	0.00734 (15)	0.02819 (17)	0.02745 (14)
C1	0.0752 (19)	0.0483 (15)	0.0458 (15)	0.0241 (14)	0.0182 (14)	0.0259 (13)
C2	0.0615 (16)	0.0352 (13)	0.0453 (14)	0.0094 (12)	0.0203 (12)	0.0159 (11)
C3	0.0572 (15)	0.0369 (13)	0.0378 (13)	0.0036 (11)	0.0109 (11)	0.0103 (11)
C4	0.0468 (13)	0.0346 (12)	0.0323 (11)	0.0084 (10)	0.0083 (10)	0.0121 (10)
C5	0.0437 (13)	0.0369 (12)	0.0352 (12)	0.0119 (10)	0.0100 (10)	0.0113 (10)
C6	0.0460 (13)	0.0358 (12)	0.0345 (12)	0.0060 (10)	0.0040 (10)	0.0119 (10)
C7	0.0357 (12)	0.0496 (14)	0.0428 (13)	0.0047 (11)	−0.0023 (10)	0.0134 (12)
C8	0.0321 (12)	0.0419 (13)	0.0355 (12)	−0.0009 (10)	−0.0081 (9)	0.0094 (10)
C9	0.0581 (16)	0.0427 (14)	0.0511 (15)	0.0044 (12)	0.0053 (12)	0.0185 (12)
C10	0.074 (2)	0.0440 (16)	0.074 (2)	0.0150 (15)	0.0095 (17)	0.0142 (15)
C11	0.069 (2)	0.065 (2)	0.0518 (17)	0.0155 (16)	0.0109 (14)	0.0036 (15)
C12	0.080 (2)	0.079 (2)	0.0422 (15)	0.0184 (18)	0.0089 (14)	0.0238 (15)
C13	0.0682 (18)	0.0556 (17)	0.0426 (14)	0.0191 (14)	0.0021 (13)	0.0194 (13)
N1	0.0618 (13)	0.0493 (13)	0.0397 (11)	0.0181 (11)	0.0045 (10)	0.0199 (10)
N2	0.0435 (11)	0.0369 (10)	0.0337 (10)	0.0055 (9)	−0.0001 (8)	0.0099 (8)
N3	0.0544 (12)	0.0349 (10)	0.0324 (10)	−0.0006 (9)	−0.0056 (9)	0.0125 (8)
O1	0.0670 (12)	0.0366 (9)	0.0466 (10)	−0.0043 (8)	−0.0091 (9)	0.0177 (8)

Br1—C2	1.898 (3)	C7—C8	1.507 (3)
C1—N1	1.350 (4)	C7—H7A	0.9700
C1—C2	1.368 (4)	C7—H7B	0.9700
C1—H1	0.9300	C8—C9	1.372 (4)
C2—C3	1.392 (4)	C8—C13	1.380 (4)
C3—C4	1.373 (3)	C9—C10	1.381 (4)
C3—H3	0.9300	C9—H9	0.9300
C4—N3	1.385 (3)	C10—C11	1.375 (5)
C4—C5	1.392 (3)	C10—H10	0.9300
C5—N1	1.320 (3)	C11—C12	1.357 (5)
C5—N2	1.380 (3)	C11—H11	0.9300
C6—O1	1.227 (3)	C12—C13	1.378 (4)
C6—N3	1.367 (3)	C12—H12	0.9300
C6—N2	1.381 (3)	C13—H13	0.9300
C7—N2	1.458 (3)	N3—H14	0.8600
N1—C1—C2	123.9 (2)	C9—C8—C7	120.9 (2)
N1—C1—H1	118.1	C13—C8—C7	120.5 (2)
C2—C1—H1	118.1	C8—C9—C10	120.6 (3)
C1—C2—C3	121.7 (2)	C8—C9—H9	119.7
C1—C2—Br1	119.55 (19)	C10—C9—H9	119.7
C3—C2—Br1	118.8 (2)	C11—C10—C9	120.0 (3)
C4—C3—C2	115.1 (2)	C11—C10—H10	120.0
C4—C3—H3	122.5	C9—C10—H10	120.0
C2—C3—H3	122.5	C12—C11—C10	119.8 (3)
C3—C4—N3	133.9 (2)	C12—C11—H11	120.1
C3—C4—C5	119.2 (2)	C10—C11—H11	120.1
N3—C4—C5	106.8 (2)	C11—C12—C13	120.2 (3)
N1—C5—N2	125.9 (2)	C11—C12—H12	119.9
N1—C5—C4	126.6 (2)	C13—C12—H12	119.9
N2—C5—C4	107.5 (2)	C12—C13—C8	120.7 (3)
O1—C6—N3	127.5 (2)	C12—C13—H13	119.6
O1—C6—N2	125.6 (2)	C8—C13—H13	119.6
N3—C6—N2	107.0 (2)	C5—N1—C1	113.6 (2)
N2—C7—C8	113.10 (19)	C5—N2—C6	109.01 (19)
N2—C7—H7A	109.0	C5—N2—C7	126.9 (2)
C8—C7—H7A	109.0	C6—N2—C7	124.1 (2)
N2—C7—H7B	109.0	C6—N3—C4	109.67 (19)
C8—C7—H7B	109.0	C6—N3—H14	125.2
H7A—C7—H7B	107.8	C4—N3—H14	125.2
C9—C8—C13	118.6 (2)
N1—C1—C2—C3	0.8 (4)	C7—C8—C13—C12	178.3 (3)
N1—C1—C2—Br1	−178.9 (2)	N2—C5—N1—C1	−179.1 (2)
C1—C2—C3—C4	−0.6 (4)	C4—C5—N1—C1	0.3 (4)
Br1—C2—C3—C4	179.11 (17)	C2—C1—N1—C5	−0.6 (4)
C2—C3—C4—N3	179.7 (2)	N1—C5—N2—C6	179.6 (2)
C2—C3—C4—C5	0.3 (3)	C4—C5—N2—C6	0.2 (2)
C3—C4—C5—N1	−0.1 (4)	N1—C5—N2—C7	−2.6 (4)
N3—C4—C5—N1	−179.7 (2)	C4—C5—N2—C7	178.0 (2)
C3—C4—C5—N2	179.3 (2)	O1—C6—N2—C5	179.4 (2)
N3—C4—C5—N2	−0.3 (3)	N3—C6—N2—C5	−0.1 (3)
N2—C7—C8—C9	−93.6 (3)	O1—C6—N2—C7	1.5 (4)
N2—C7—C8—C13	86.6 (3)	N3—C6—N2—C7	−177.9 (2)
C13—C8—C9—C10	1.2 (4)	C8—C7—N2—C5	−86.5 (3)
C7—C8—C9—C10	−178.5 (3)	C8—C7—N2—C6	91.0 (3)
C8—C9—C10—C11	0.0 (5)	O1—C6—N3—C4	−179.6 (2)
C9—C10—C11—C12	−1.1 (5)	N2—C6—N3—C4	−0.1 (3)
C10—C11—C12—C13	0.9 (5)	C3—C4—N3—C6	−179.2 (3)
C11—C12—C13—C8	0.4 (5)	C5—C4—N3—C6	0.3 (3)
C9—C8—C13—C12	−1.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H14···O1i	0.86	1.95	2.789 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H14⋯O1i	0.86	1.95	2.789 (3)	166

Symmetry code: (i) .