6-Bromo-3-methyl-2-phenyl-3H-imidazo[4,5-b]pyridine.

The two fused five- and six-membered rings building the mol-ecule of the title compound, C(13)H(10)BrN(3), are approximately planar, the largest deviation from the mean plane being 0.004 (2) Å. The dihedral angle between the imidazo[4,5-b]pyridine mean plane and that of the phenyl ring is 41.84 (11)°. The structure is held together by slipped π-π stacking between symmetry-related mol-ecules, with an inter-planar distance of 3.583 (1) Å and a centroid-centroid vector of 3.670 (2) Å.

Related literature

For background regarding biological activity of imidazo[4,5-b]pyridines, see: Cristalli et al. (1995 ▶); Bukowski & Kaliszan (1991 ▶); Aridoss et al. (2006 ▶); Bavetsias et al. (2007 ▶). For background to their pharmacological activity, see: Chen & Dost (1992 ▶); Weier et al. (1993 ▶).

Experimental

Crystal data

C13H10BrN3

M = 288.15

Orthorhombic,

a = 13.7138 (4) Å

b = 6.7088 (2) Å

c = 25.3217 (7) Å

V = 2329.68 (12) Å3

Z = 8

Mo Kα radiation

μ = 3.51 mm−1

T = 298 K

0.60 × 0.30 × 0.06 mm

Data collection

Bruker SMART CCD three-circle diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.227, T max = 0.825

13535 measured reflections

2378 independent reflections

1804 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.04

2378 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.40 e Å−3

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: ORTEPIII (Burnett & Johnson, 1996 ▶) and 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/S1600536811022318/dn2697sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022318/dn2697Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022318/dn2697Isup3.cml

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

C13H10BrN3	F(000) = 1152
Mr = 288.15	Dx = 1.643 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5157 reflections
a = 13.7138 (4) Å	θ = 3.0–29.6°
b = 6.7088 (2) Å	µ = 3.51 mm−1
c = 25.3217 (7) Å	T = 298 K
V = 2329.68 (12) Å3	Platelet, colourless
Z = 8	0.60 × 0.30 × 0.06 mm

Bruker CCD three-circle diffractometer	2378 independent reflections
Radiation source: fine-focus sealed tube	1804 reflections with I > 2σ(I)
graphite	Rint = 0.047
ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = 0→17
Tmin = 0.227, Tmax = 0.825	k = 0→8
13535 measured reflections	l = 0→31

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: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0361P)2 + 1.2509P] where P = (Fo2 + 2Fc2)/3
2378 reflections	(Δ/σ)max = 0.002
155 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.40 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 > 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	0.65259 (2)	1.16657 (6)	0.626463 (10)	0.06788 (15)
N1	0.60483 (17)	0.7251 (3)	0.51723 (8)	0.0509 (6)
N2	0.60942 (14)	0.7570 (3)	0.42245 (7)	0.0396 (4)
N3	0.64274 (15)	1.0833 (3)	0.41558 (8)	0.0425 (5)
C1	0.6160 (2)	0.8347 (4)	0.56091 (10)	0.0528 (7)
H1	0.6093	0.7719	0.5934	0.063*
C2	0.63682 (17)	1.0361 (4)	0.56042 (9)	0.0477 (6)
C3	0.64811 (18)	1.1434 (4)	0.51422 (10)	0.0464 (6)
H3	0.6620	1.2790	0.5138	0.056*
C4	0.63692 (16)	1.0313 (4)	0.46819 (9)	0.0385 (5)
C5	0.61634 (17)	0.8291 (3)	0.47310 (9)	0.0386 (5)
C6	0.62568 (16)	0.9162 (4)	0.38966 (9)	0.0369 (5)
C7	0.62409 (16)	0.9055 (4)	0.33165 (9)	0.0378 (5)
C8	0.58108 (18)	1.0590 (4)	0.30370 (9)	0.0463 (6)
H8	0.5525	1.1644	0.3218	0.056*
C9	0.5801 (2)	1.0574 (5)	0.24902 (10)	0.0561 (7)
H9	0.5506	1.1610	0.2306	0.067*
C10	0.6226 (2)	0.9037 (5)	0.22203 (11)	0.0590 (8)
H10	0.6217	0.9025	0.1853	0.071*
C11	0.6665 (2)	0.7515 (6)	0.24919 (12)	0.0641 (8)
H11	0.6957	0.6476	0.2307	0.077*
C12	0.66776 (19)	0.7512 (5)	0.30402 (11)	0.0531 (7)
H12	0.6978	0.6475	0.3222	0.064*
C13	0.5829 (2)	0.5528 (4)	0.40922 (12)	0.0607 (8)
H13A	0.5461	0.5518	0.3770	0.091*
H13B	0.5441	0.4973	0.4372	0.091*
H13C	0.6409	0.4746	0.4048	0.091*

	U11	U22	U33	U12	U13	U23
Br1	0.0669 (2)	0.0970 (3)	0.03975 (18)	−0.00449 (16)	−0.00264 (12)	−0.01196 (14)
N1	0.0583 (14)	0.0484 (13)	0.0460 (12)	−0.0094 (11)	−0.0071 (10)	0.0159 (10)
N2	0.0467 (11)	0.0275 (10)	0.0445 (11)	−0.0009 (9)	−0.0056 (9)	0.0035 (9)
N3	0.0584 (13)	0.0312 (10)	0.0379 (10)	−0.0030 (9)	0.0000 (9)	0.0023 (9)
C1	0.0529 (15)	0.0641 (19)	0.0414 (14)	−0.0091 (14)	−0.0064 (11)	0.0176 (13)
C2	0.0411 (13)	0.0662 (19)	0.0358 (12)	−0.0012 (12)	−0.0042 (10)	0.0006 (12)
C3	0.0526 (15)	0.0436 (15)	0.0430 (13)	−0.0035 (11)	−0.0023 (11)	−0.0017 (11)
C4	0.0427 (13)	0.0344 (13)	0.0385 (12)	−0.0008 (10)	−0.0019 (9)	0.0043 (10)
C5	0.0385 (12)	0.0347 (12)	0.0426 (12)	−0.0022 (10)	−0.0061 (10)	0.0066 (10)
C6	0.0381 (12)	0.0316 (12)	0.0410 (12)	0.0030 (10)	−0.0028 (10)	0.0016 (10)
C7	0.0362 (11)	0.0391 (13)	0.0380 (12)	−0.0019 (10)	0.0003 (9)	−0.0014 (10)
C8	0.0522 (14)	0.0459 (15)	0.0408 (13)	0.0073 (12)	0.0051 (11)	0.0026 (11)
C9	0.0575 (16)	0.071 (2)	0.0402 (14)	0.0032 (14)	0.0022 (12)	0.0109 (13)
C10	0.0541 (15)	0.084 (2)	0.0389 (14)	−0.0069 (16)	0.0070 (12)	−0.0068 (14)
C11	0.0615 (19)	0.071 (2)	0.0594 (18)	0.0084 (16)	0.0145 (14)	−0.0249 (17)
C12	0.0514 (16)	0.0528 (16)	0.0551 (16)	0.0114 (13)	0.0018 (12)	−0.0064 (14)
C13	0.087 (2)	0.0329 (14)	0.0622 (17)	−0.0136 (14)	−0.0098 (15)	−0.0003 (13)

Br1—C2	1.900 (3)	C7—C8	1.382 (3)
N1—C5	1.327 (3)	C7—C12	1.386 (4)
N1—C1	1.337 (3)	C8—C9	1.385 (3)
N2—C6	1.371 (3)	C8—H8	0.9300
N2—C5	1.374 (3)	C9—C10	1.367 (4)
N2—C13	1.456 (3)	C9—H9	0.9300
N3—C6	1.320 (3)	C10—C11	1.371 (5)
N3—C4	1.380 (3)	C10—H10	0.9300
C1—C2	1.381 (4)	C11—C12	1.388 (4)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.382 (4)	C12—H12	0.9300
C3—C4	1.395 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.391 (3)	C13—H13C	0.9600
C6—C7	1.471 (3)
C5—N1—C1	113.2 (2)	C8—C7—C6	118.8 (2)
C6—N2—C5	106.23 (19)	C12—C7—C6	122.3 (2)
C6—N2—C13	129.4 (2)	C7—C8—C9	120.7 (3)
C5—N2—C13	124.3 (2)	C7—C8—H8	119.7
C6—N3—C4	104.8 (2)	C9—C8—H8	119.7
N1—C1—C2	123.7 (2)	C10—C9—C8	120.1 (3)
N1—C1—H1	118.2	C10—C9—H9	119.9
C2—C1—H1	118.2	C8—C9—H9	119.9
C1—C2—C3	122.7 (2)	C9—C10—C11	119.9 (3)
C1—C2—Br1	117.80 (19)	C9—C10—H10	120.1
C3—C2—Br1	119.5 (2)	C11—C10—H10	120.1
C2—C3—C4	114.5 (2)	C10—C11—C12	120.6 (3)
C2—C3—H3	122.8	C10—C11—H11	119.7
C4—C3—H3	122.8	C12—C11—H11	119.7
N3—C4—C5	110.2 (2)	C7—C12—C11	119.9 (3)
N3—C4—C3	131.6 (2)	C7—C12—H12	120.1
C5—C4—C3	118.2 (2)	C11—C12—H12	120.1
N1—C5—N2	126.4 (2)	N2—C13—H13A	109.5
N1—C5—C4	127.7 (2)	N2—C13—H13B	109.5
N2—C5—C4	105.9 (2)	H13A—C13—H13B	109.5
N3—C6—N2	112.9 (2)	N2—C13—H13C	109.5
N3—C6—C7	122.7 (2)	H13A—C13—H13C	109.5
N2—C6—C7	124.3 (2)	H13B—C13—H13C	109.5
C8—C7—C12	118.9 (2)