In the title compound, C(13)H(9)ClFNO(3), the benzene rings are oriented at a dihedral angle of 41.23 (5)°. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules in a herring-bone arrangement along the b axis and weak π-π contacts between the benzene rings [centroid-centroid distance = 3.881 (1) Å] may further stabilize the structure.

In the title compound, C15H12ClNO2S, the indole ring is essentially planar (r.m.s. deviation = 0.0107 Å) and makes a dihedral angle of 85.01 (6)° with the benzene ring. In the crystal, three C-H⋯O hydrogen bonds result in a hydrogen-bonded spiral running parallel to the c axis.

The title mol-ecule, C(9)H(6)ClNO(2), is essentially planar; the maximum deviation of the indoline ring system is 0.027 (3) Å and the substituents do not deviate by more than 0.075 (2) Å from this plane. Inter-molecular C-H⋯O hydrogen bonds consolidate the crystal structure.

Treatment of 1-(5-bromo-2-chloro-6-methylpyrimidin-4-yl)-1-methylhydrazine with dimethylthiocarbamoylchloride gave 7-chloro-N,N,1,5-tetramethyl-1H-pyrimido[4,5-e][1,3,4]thiadiazin-3-amine in basic acetonitrile. The latter compounds were reacted with secondary amines in boiling ethanol to afford the related 7-amino derivatives.

The benzene rings of the biphenyl group in the title compound, C(20)H(14)ClN(3)O(3)S, are nearly coplanar [maximum deviation = 0.20 (3) Å]. The mean plane of the biphenyl group forms a dihedral angle of 5.24 (7)° with the aromatic ring of the nitro-chloro-benzene group. Intra-molecular N-H⋯Cl, N-H⋯O and C-H⋯S hydrogen bonds stabilize the cis-trans conformation of the mol-ecule. In the crystal, ...