Abstract
The novel hydrazone-containing thieno[2,3-d]pyrimidine, namely, N '-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)-2-(4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazide 4 was synthesized in a very good yield from the reaction of the triketoester 1 or ninhydrin 2 with the exocyclic acetohydrazide 3 in methanol. Good-quality crystals of 4 were obtained by recrystallization of the compound from the DMF/MeOH solvent mixture. The target product 4 crystallized in the triclinic crystal system and P-1 space group. The topology analysis of molecular packing indicated that the H horizontal ellipsis H (30.4%), O horizontal ellipsis H (22.0%) and H horizontal ellipsis C (17.0%) contacts are the most dominant intermolecular interactions in the crystal of 4, while the O horizontal ellipsis H, N horizontal ellipsis H, H horizontal ellipsis C, N horizontal ellipsis C, O horizontal ellipsis C, C horizontal ellipsis C and O horizontal ellipsis O are the only contacts which have shorter interaction distances than the vdWs radii sum of the interacting atoms. The structure of 4 is optimized and the calculated structure showed good agreement with the experimental one. Additionally, MEP, HOMO, LUMO and the reactivity descriptors were calculated.