2-(5,6-Dibromo-7-methyl-3H-imidazo[4,5-b]pyridin-2-yl)phenol.

In the title compound, C(13)H(9)Br(2)N(3)O, the mol-ecular skeleton, influenced by an intra-molecular O-H⋯N hydrogen bond, is roughly planar, with a mean deviation of 0.033 Å. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [100]. Weak inter-molecular π-π inter-actions [centroid-centroid distances = 3.760 (3) and 3.723 (3) Å] further consolidate the packing.

Related literature

For background to the use of imidazole and its derivatives in transition metal complexes, see: Huang et al. (2004 ▶). For related structures, see: Eltayeb et al. (2009 ▶); Xiao et al. (2009 ▶); Elerman & Kabak (1997 ▶).

Experimental

Crystal data

C13H9Br2N3O

M = 383.05

Orthorhombic,

a = 13.181 (5) Å

b = 8.494 (3) Å

c = 22.692 (8) Å

V = 2540.5 (16) Å3

Z = 8

Mo Kα radiation

μ = 6.38 mm−1

T = 293 K

0.31 × 0.28 × 0.24 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.243, T max = 0.310

11656 measured reflections

2234 independent reflections

1706 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.138

S = 1.08

2234 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.88 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: SHELXTL (Sheldrick, 2008b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810045277/cv2784sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045277/cv2784Isup2.hkl

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

C13H9Br2N3O	F(000) = 1488
Mr = 383.05	Dx = 2.003 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1452 reflections
a = 13.181 (5) Å	θ = 2.9–24.6°
b = 8.494 (3) Å	µ = 6.38 mm−1
c = 22.692 (8) Å	T = 293 K
V = 2540.5 (16) Å3	Block, orange–yellow
Z = 8	0.31 × 0.28 × 0.24 mm

Bruker APEXII CCD area-detector diffractometer	2234 independent reflections
Radiation source: fine-focus sealed tube	1706 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −15→15
Tmin = 0.243, Tmax = 0.310	k = −9→10
11656 measured reflections	l = −24→26

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0692P)2 + 6.558P] where P = (Fo2 + 2Fc2)/3
2234 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.88 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	0.27968 (6)	1.22305 (9)	0.48970 (3)	0.0618 (3)
Br2	0.51701 (6)	1.19032 (9)	0.54180 (3)	0.0669 (3)
O1	0.0310 (3)	0.7707 (6)	0.73898 (19)	0.0541 (12)
H1	0.0614	0.8111	0.7113	0.081*
N1	0.3413 (3)	0.8522 (5)	0.7102 (2)	0.0380 (10)
H1A	0.4011	0.8215	0.7306	0.046*
N2	0.1806 (3)	0.8887 (5)	0.68102 (19)	0.0365 (10)
N3	0.4280 (4)	1.0090 (7)	0.6313 (2)	0.0615 (15)
C1	0.3468 (4)	0.9445 (6)	0.6601 (2)	0.0348 (12)
C2	0.2452 (4)	0.9659 (6)	0.6416 (2)	0.0350 (12)
C3	0.2226 (4)	1.0517 (7)	0.5909 (2)	0.0432 (13)
C4	0.3060 (4)	1.1146 (7)	0.5612 (2)	0.0414 (13)
C5	0.4049 (4)	1.0950 (6)	0.5811 (2)	0.0400 (13)
C6	0.1127 (5)	1.0806 (9)	0.5643 (3)	0.0680 (19)
H6A	0.0923	1.1873	0.5717	0.102*
H6B	0.0653	1.0098	0.5825	0.102*
H6C	0.1140	1.0621	0.5226	0.102*
C7	0.2410 (4)	0.8221 (6)	0.7213 (2)	0.0357 (12)
C8	0.2041 (4)	0.7275 (6)	0.7696 (2)	0.0354 (12)
C9	0.0988 (5)	0.7064 (7)	0.7768 (3)	0.0431 (13)
C10	0.0636 (5)	0.6169 (8)	0.8237 (3)	0.0578 (17)
H10	−0.0057	0.6022	0.8288	0.069*
C11	0.1315 (5)	0.5488 (8)	0.8632 (3)	0.0604 (18)
H11	0.1074	0.4895	0.8947	0.072*
C12	0.2329 (5)	0.5690 (8)	0.8558 (3)	0.0536 (16)
H12	0.2779	0.5226	0.8821	0.064*
C13	0.2693 (4)	0.6560 (7)	0.8104 (3)	0.0453 (14)
H13	0.3390	0.6686	0.8063	0.054*

	U11	U22	U33	U12	U13	U23
Br1	0.0851 (6)	0.0621 (5)	0.0383 (4)	0.0019 (4)	−0.0058 (3)	0.0082 (3)
Br2	0.0640 (5)	0.0757 (5)	0.0609 (5)	−0.0265 (4)	0.0124 (3)	0.0054 (4)
O1	0.029 (2)	0.079 (3)	0.054 (3)	0.0054 (19)	0.0065 (19)	0.007 (2)
N1	0.027 (2)	0.048 (3)	0.039 (3)	−0.0008 (19)	−0.0055 (19)	0.001 (2)
N2	0.028 (2)	0.045 (3)	0.037 (3)	0.0009 (18)	−0.0012 (19)	−0.002 (2)
N3	0.056 (3)	0.068 (4)	0.060 (4)	−0.006 (3)	0.003 (3)	−0.005 (3)
C1	0.029 (3)	0.043 (3)	0.033 (3)	−0.004 (2)	0.000 (2)	−0.003 (2)
C2	0.033 (3)	0.040 (3)	0.032 (3)	−0.001 (2)	0.000 (2)	−0.004 (2)
C3	0.048 (3)	0.046 (3)	0.036 (3)	0.007 (3)	−0.002 (3)	−0.005 (3)
C4	0.050 (3)	0.041 (3)	0.034 (3)	−0.002 (3)	0.000 (3)	−0.003 (2)
C5	0.045 (3)	0.040 (3)	0.036 (3)	−0.007 (2)	0.006 (3)	0.000 (2)
C6	0.071 (5)	0.076 (5)	0.057 (4)	0.012 (4)	0.011 (4)	0.010 (4)
C7	0.031 (3)	0.040 (3)	0.036 (3)	−0.001 (2)	0.004 (2)	−0.007 (2)
C8	0.038 (3)	0.034 (3)	0.034 (3)	−0.002 (2)	0.004 (2)	−0.004 (2)
C9	0.044 (3)	0.044 (3)	0.041 (3)	0.001 (3)	0.009 (3)	−0.006 (3)
C10	0.054 (4)	0.061 (4)	0.059 (4)	−0.008 (3)	0.023 (3)	−0.001 (3)
C11	0.082 (5)	0.051 (4)	0.048 (4)	−0.004 (3)	0.018 (3)	0.006 (3)
C12	0.066 (4)	0.052 (4)	0.043 (4)	0.001 (3)	−0.004 (3)	0.008 (3)
C13	0.042 (3)	0.047 (3)	0.047 (4)	−0.001 (3)	−0.006 (3)	0.003 (3)

Br1—C4	1.897 (6)	C4—C5	1.389 (8)
Br2—C5	1.907 (5)	C6—H6A	0.9600
O1—C9	1.354 (7)	C6—H6B	0.9600
O1—H1	0.8200	C6—H6C	0.9600
N1—C7	1.369 (7)	C7—C8	1.442 (8)
N1—C1	1.382 (7)	C8—C13	1.402 (8)
N1—H1A	0.9504	C8—C9	1.408 (8)
N2—C7	1.338 (7)	C9—C10	1.388 (8)
N2—C2	1.398 (7)	C10—C11	1.392 (9)
N3—C1	1.370 (7)	C10—H10	0.9300
N3—C5	1.387 (8)	C11—C12	1.358 (9)
C1—C2	1.415 (7)	C11—H11	0.9300
C2—C3	1.394 (8)	C12—C13	1.355 (8)
C3—C4	1.396 (8)	C12—H12	0.9300
C3—C6	1.589 (9)	C13—H13	0.9300
Cg1···Cg2i	3.760 (3)	Cg1···Cg3ii	3.723 (3)
C9—O1—H1	109.5	C3—C6—H6C	109.5
C7—N1—C1	107.9 (4)	H6A—C6—H6C	109.5
C7—N1—H1A	131.3	H6B—C6—H6C	109.5
C1—N1—H1A	120.8	N2—C7—N1	111.7 (5)
C7—N2—C2	105.9 (4)	N2—C7—C8	123.6 (5)
C1—N3—C5	115.6 (5)	N1—C7—C8	124.7 (5)
N3—C1—N1	131.4 (5)	C13—C8—C9	118.1 (5)
N3—C1—C2	123.1 (5)	C13—C8—C7	122.4 (5)
N1—C1—C2	105.6 (4)	C9—C8—C7	119.5 (5)
C3—C2—N2	130.1 (5)	O1—C9—C10	119.1 (6)
C3—C2—C1	121.0 (5)	O1—C9—C8	121.6 (5)
N2—C2—C1	109.0 (5)	C10—C9—C8	119.3 (6)
C2—C3—C4	115.5 (5)	C9—C10—C11	120.4 (6)
C2—C3—C6	126.1 (5)	C9—C10—H10	119.8
C4—C3—C6	118.4 (5)	C11—C10—H10	119.8
C5—C4—C3	122.4 (5)	C12—C11—C10	120.0 (6)
C5—C4—Br1	120.5 (4)	C12—C11—H11	120.0
C3—C4—Br1	117.1 (4)	C10—C11—H11	120.0
N3—C5—C4	122.5 (5)	C13—C12—C11	120.8 (6)
N3—C5—Br2	115.9 (4)	C13—C12—H12	119.6
C4—C5—Br2	121.6 (4)	C11—C12—H12	119.6
C3—C6—H6A	109.5	C12—C13—C8	121.5 (5)
C3—C6—H6B	109.5	C12—C13—H13	119.3
H6A—C6—H6B	109.5	C8—C13—H13	119.3

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1iii	0.95	1.90	2.839 (6)	171
O1—H1···N2	0.82	1.84	2.573 (6)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.95	1.90	2.839 (6)	171
O1—H1⋯N2	0.82	1.84	2.573 (6)	149

Symmetry code: (i) .