Crystal Structure and Conformation Study of 3-Methyl-2, 6-bis (4-chlorophenyl) Piperidin-4-one Thiosemicarbazone Derivative

Abstract  

The 1, 3-dipolar cycloaddition reactions with trans azomethine ylide produce spirooxindole derivatives, which are active against certain bacterial pathogens. Spirooxindole ring systems have a very important place in medicinal chemistry because they are the central skeleton for numerous alkaloids and have potential biological activity. This newly synthesized target molecule, PSSPI was crystallized and its X-ray crystal structure has been derived. The crystallographic data of PSSPI are: C₃₄H₃₈N₂O₃; M.W = 522.7, Monoclinic, P2₁/a, with cell parameters a = 11.959(6) ?, b = 19.308(3) ?, c = 13.452(6) ?, β = 107.81(4)°; V = 2957(2) ?³, Z = 4, D _cal = 1.174 mg/m³, λ (Mo K _α ) = 0.71073 ?. Based on the crystal structure, the piperidine, pyrrolidine and cyclohexanone rings adopt half-chair, envelop and twisted sofa conformations respectively. The rings oxindole and cyclohexanone are parallel to each other but perpendicular to the pyrrolidine ring. C–H···N, C–H···O and N–H···O types of intra and intermolecular interactions control the molecules in the crystal packing.