Crystal structure of 1-amino-3-(4-chloro­phen­yl)-2-cyano-3H-benzo[4,5]thia­zolo[3,2-a]pyridine-4-carboxamide

Abstract

The tricyclic ring system of the title compound departs from planarity in the region of the sp³ carbon atom. The three-dimensional packing involves four classical hydrogen bonds and one N⋯Cl halogen bond.

In the structure of the title compound, C₁₉H₁₃ClN₄OS, the four atoms of the pyridinic ring that are not fused with the thia­zole, including the sp³ C atom, lie significantly outside the benzo­thia­zole plane. A short intra­molecular 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 inter­connected layer structures. The first, parallel to the bc plane, involves three classical hydrogen bonds N—H_amine⋯O (one of two), N—H_amine⋯Cl and one N—H_amide ⋯N_cyano; the second, parallel to the ab plane, involves two hydrogen bonds, N—H_amide⋯O and the second N—H_amine⋯O, together with the short and linear contact N_cyano⋯Cl—C, which may be regarded as a halogen bond.