6-Bromo-1-methyl-4-[2-(4-methylbenzylidene)hydrazinylidene]-3H-2λ6,1-benzothiazine-2,2-dione

In the title compound, C17H16BrN3O2S, the two fused rings are twisted by a dihedral angle of 6.61 (15)°. The thiazine ring adopts a sofa conformation. The toluene ring is oriented at dihedral angles of 15.5 (2) and 20.6 (2)° with respect to the bromobenzene and thiazine rings, respectively. The benzylidene system is approximately planar [r.m.s. deviation = 0.0388 Å]. In the cyrstal, weak intermolecular C—H⋯O hydrogen bonds connects the molecules into a chain along the b axis.

In the title compound, C 17 H 16 BrN 3 O 2 S, the two fused rings are twisted by a dihedral angle of 6.61 (15) . The thiazine ring adopts a sofa conformation. The toluene ring is oriented at dihedral angles of 15.5 (2) and 20.6 (2) with respect to the bromobenzene and thiazine rings, respectively. The benzylidene system is approximately planar [r.m.s. deviation = 0.0388 Å ]. In the cyrstal, weak intermolecular C-HÁ Á ÁO hydrogen bonds connects the molecules into a chain along the b axis.   Table 1 Hydrogen-bond geometry (Å , ).
The benzylidene moiety (C9-C16/N1/N2) is also very near to planerity as showing the r. m. s. deviation of 0.0388Å and is oriented at a dihedral angle 15.02 (12)° with respect to the benzene ring (C1-C6). The fused aromatic (C1-C6) and thiazine (C1/C6/C7/C8/N1/S1) rings are twisted at a dihedral angle 6.61 (15)°. The oxygen atom from SO 2 group is involved in weak C-H···O type hydrogen bonding interaction, which connects the molecules in a zig-zag mode along the b-axis.
The crystal structures of several molecules related to the title compound have been reported (Arshad et al., 2009;Shafiq et al., 2009).

Experimental
The synthesis of the title compound has already been reportrd (Shafiq et al., 2011). It was recrystalized from a solution in dry ethanol.

Refinement
All H-atoms were positioned at idealized geometry with C aromatic -H = 0.93 Å and C methyl -H = 0.96 Å and were refined using a riding model with U iso (H) = 1.2 U eq (C) for aromatic & U iso (H) = 1.5 U eq (C) for methyl carbon atoms. The reflection 0 0 1 has been omitted in final refinement. An absolute structure was determined (Flack, 1983) using 1771 Friedel pairs.

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.