4-Bromo-2,6-dimethylaniline

The asymmetric unit of the title compound, C8H10BrN, contains two independent molecules. The Br, N and methyl group C atoms lie in the benzene ring planes. In the crystal structure, N—H⋯N hydrogen bonds link the molecules.

The asymmetric unit of (I) contains two independent molecules ( Fig. 1), in which the bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987). The Br, N and C atoms of the methyl groups lie in the benzene ring planes.
In the crystal structure, intermolecular N-H···N hydrogen bonds (Table 2) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

S2. Experimental
The title compound, (I), was prepared by the literature method (Heravi et al., 2005). The crystals were obtained by dissolving (I) (0.5 g) in hexane (20 ml) and evaporating the solvent slowly at room temperature for about 7 d.

S3. Refinement
H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with U iso (H) = xU eq (C), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Figure 1
The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. supporting information sup-2 Acta Cryst. (2008). E64, o220

Figure 2
A packing diagram of (I). Hydrogen bonds are shown as dashed lines. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.002 Δρ max = 0.24 e Å −3 Δρ min = −0.25 e Å −3 Special details 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 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 R-factors(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.