4-Bromo-2-chloroaniline

The title compound, C6H5BrClN, is almost planar (r.m.s. deviation = 0.018 Å). In the crystal, molecules are linked by intermolecular N—H⋯N and weak N—H⋯Br hydrogen bonds, generating sheets.


Experimental
The tiltle compound was prepared according to a previously reported method (Ault & Kraig, 1966). Colourless needles of (I) were obtained by slow evaporation of a petroleum ether solution.

Refinement
The hydrogen atoms were positioned geometrically, with C-H = 0.93, 0.98, 0.97 and 0.96 Å for phenyl, methine, methylene and methyl H atoms, respectively, and were included in the refinement in the riding model approximation. The displacement parameters of methyl H atoms were set to 1.5U eq (C), while those of other H atoms were set to 1.2U eq (C). In the absence of significant anomalous scattering effects, Friedel pairs were merged. Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids.

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 > 2sigma(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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )