2,6-Dibromo-4-butylaniline

In the title compound, C10H13Br2N, the amino N atom is essentially coplanar with the benzene ring, with an r.m.s. deviation of 0.004 Å. Weak intramolecular N—H⋯Br hydrogen bonds occur. In the crystal, molecules are linked into a zigzag chain parallel to the b axis by weak N—H⋯N hydrogen bonds.

In the title compound, C 10 H 13 Br 2 N, the amino N atom is essentially coplanar with the benzene ring, with an r.m.s. deviation of 0.004 Å . Weak intramolecular N-HÁ Á ÁBr hydrogen bonds occur. In the crystal, molecules are linked into a zigzag chain parallel to the b axis by weak N-HÁ Á ÁN hydrogen bonds.
L. Zhao and L.-P. Feng

Comment
In recent years there has been a rapidly increasing interest in the construction of various kinds of supramolecular systems for understanding molecular self-assembly principles and for designing molecular recognition devices (Fender et al., 2002;Kryatova et al., 2004;Pedersen, 1967). The supramolecular system generally refers to an assembly of molecules which are not covalently connected but assembled by other weak intermolecular interactions, such as hydrogen bonds (Grabowski, 2005;Lehn, 1995;Scheiner, 1997). We report here the crystal structure of the title compound, 2,6-dibromo-4-butylaniline.
In the title compound ( Fig.1), the N atom of the amine group is essentially coplanar with the phenyl ring, with a r.m.s. deviation of 0.004 Å. This planar conformation might be resulting from weak intramolecular N-H···Br hydrogen bonds ( Table   1). The butyl group is twisted with respect to the phenyl ring resulting in torsion angles of -179.1 (7)° for C9-C8-C7-C6 and -174.7 (7)° for C7-C8-C9-C10. Bond lengths and angles lie within normal ranges.
In the crystal structure, the organic molecules are linked to form a one-dimensional chain along b axis by N1-H···N1 hydrogen bonds (Table 1, Fig.2).

Refinement
All H atoms attached to C and N atoms were calculated geometrically and treated as riding on their parent atoms with C-H = 0.93 Å (aromatic), 0.96 Å (methyl), 0.97 Å (methylene) and N-H = 0.86 Å, with U iso (H) = 1.2Ueq(C, N) or U iso (H) = 1.5Ueq(C methyl ). Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. 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.

Figures
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )