Methyl 2-amino-5-bromobenzoate

In the title compound, C8H8BrNO2, the dihedral angle between the aromatic ring and the methyl acetate side chain is 5.73 (12)°. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond, generating an S(6) ring. In the crystal, molecules are connected by N—H⋯O interactions, generating zigzag chains running along the b-axis direction.

In the title compound, C 8 H 8 BrNO 2 , the dihedral angle between the aromatic ring and the methyl acetate side chain is 5.73 (12) . The molecular conformation is stabilized by an intramolecular N-HÁ Á ÁO hydrogen bond, generating an S(6) ring. In the crystal, molecules are connected by N-HÁ Á ÁO interactions, generating zigzag chains running along the b-axis direction.
The molecular conformation is stabilized by intramolecular N-H···O hydrogen bond (Table 1, Fig. 1) forming S(6) ring (Bernstein et al., 1995). In the crystal structure, intermolecular N-H···O interactions link the neighbouring molecules to each other, producing a zigzag chain along the b axis (Table 1). Figures 2 and 3 show the packing and hydrogen bonding of the title compound viewing down the a and b-axes, respectively.

Experimental
The title compound was purchased from Sigma-Aldrich and recrystalized in methanol to yield light yellow blocks.

Refinement
In the last cycles of the refinement, 3 reflections (0 1 1), (0 -1 1) and (0 0 1) were eliminated due to being poorly measured in the vicinity of the beam stop. The H atoms of the NH 2 group were located in a difference Fourier map, and refined with a distance restraint N-H = 0.86 (2) Å. Their isotropic displacement parameters were set to be 1.2U eq (N). The other H atoms were positioned geometrically with C-H distances of 0.93 Å (aromatic) and 0.96 Å (methyl), and refined using a riding model, with U iso (H) = 1.2U eq (C) for aromatic and U iso (H) = 1.5U eq (C) for methyl. Fig. 1. The title molecule with displacement ellipsoids for non-H atoms drawn at the 50% probability level. Methyl 2-amino-5-bromobenzoate

Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted Rfactors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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.