2-[(3-Bromoanilino)methyl]-1,2-benzothiazol-3(2H)-one

The title compound, C14H11BrN2OS, was synthesized by the reaction of 1,2-benzothiazol-3(2H)-one with formalin and 3-bromoaniline in ethanol. The 1,2-benzothiazolone ring system is approximately planar [maximum deviation = 0.0142 (s.u.?) Å] and forms a dihedral angle of 79.19 (5)° with the benzene ring. In the crystal, molecules are linked by N—H⋯O, C—H⋯O and C—H⋯Br interactions.

The molecular structure of the title compound is shown in Fig. 1. In the molecule, the benzisothiazolone ring system is approximately planar with a maximum deviation from the mean plane of 0.0142 A ° for the atom C1, and the dihedral angle between the benzene ring and the benzisothiazolone ring is 79.169 (5)°. In the crystal structure, intermolecular N-H···O, C-H···O and C-H···Br hydrogen bonds (Table 1) link molecules into a three-dimensional network (Fig. 2).
Single crystals suitable for X-ray measurements were obtained by recrystallization of the title compound from trichloromethane/methanol (1:1 v/v) at room temperature.

Refinement
The amine H atom was located in a difference Fourier map and refined freely. All other H atoms were placed at calculated positions and refined in riding mode, with C-H = 0.95-0.99 Å. The U iso (H) values were constrained to be 1.5U eq (C) for the methyl H atoms or 1.2U eq (C) for the remaining H atoms.  The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.

Figure 2
A view of the C-H···O and C-H···Br interactions (dashed lines) in the crystal structure of the title compound. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq