Crystal structure of 1-amino-3-(4-chloro-phen-yl)-2-cyano-3H-benzo[4,5]thia-zolo[3,2-a]pyridine-4-carboxamide.

In the structure of the title compound, C19H13ClN4OS, the four atoms of the pyridinic ring that are not fused with the thia-zole, including the sp 3 C atom, lie significantly outside the benzo-thia-zole plane. A short intra-molecular S⋯O contact of 2.5992 (4) Å is observed. The amide NH2 group is planar, whereas the amine NH2 group is pyramidalized. The three-dimensional packing involves two inter-connected layer structures. The first, parallel to the bc plane, involves three classical hydrogen bonds N-Hamine⋯O (one of two), N-Hamine⋯Cl and one N-Hamide ⋯Ncyano; the second, parallel to the ab plane, involves two hydrogen bonds, N-Hamide⋯O and the second N-Hamine⋯O, together with the short and linear contact Ncyano⋯Cl-C, which may be regarded as a halogen bond.