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

The two fused five- and six-membered rings building the molecule of the title compound, C13H10BrN3, 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 molecules, with an interplanar distance of 3.583 (1) Å and a centroid–centroid vector of 3.670 (2) Å.

The two fused five-and six-membered rings building the molecule 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 slippedstacking between symmetry-related molecules, with an interplanar distance of 3.583 (1) Å and a centroid-centroid vector of 3.670 (2) Å .
The two fused five and six-membered rings are nearly planar with the maximum deviation of 0.004 (2) Å from N1. The dihedral angle between the imidazo[4,5-b]pyridine system and the phenyl ring is 41.84 (11)° (Fig. 1). The structure is held together by slipped π-π stacking between symmetry related molecules with interplanar distance of 3.583 (1) Å and centroid to centroid vector of 3.670 (2) Å resulting in a slippage of 0.79 Å.

Refinement
H atoms were located in a difference map and treated as riding with C-H = 0.93 Å, and 0.96 Å for aromatic and methyl respectively and with U iso (H) = 1.2 U eq (aromatic) and U iso (H) = 1.5 U eq (methyl). Fig. 1

Special details
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 F 2 against all reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on all data will be even larger.  (13)