Structural and computational insights into a thioxoacetamide: role of C=S interactions in crystal packing and molecular recognition

Thioxoamide derivatives exhibit diverse biological activities, while the relationship between their C=S-containing molecular structure, solid-state organization, and biological binding remains less explored. In this study, the newly synthesized thioxoamide N-benzyl-2-((4-chlorobenzyl)amino)-2-thioxoacetamide (1b) is structurally characterized by single-crystal X-ray diffraction and computational methods. The crystal structure reveals N–H···O and N–H···S hydrogen bonds, with Hirshfeld surface analysis providing quantitative insight into their contribution to crystal packing. DFT calculations using the B3LYP/6–311+G (d,p) level provide further insight into the electronic structure and intermolecular interaction characteristics. Molecular docking identifies favorable interactions of 1b within the active site of human thymidine kinase 1 (PDB ID: 1XBT), while ADMET analysis indicates acceptable predicted pharmacokinetic and toxicity profiles. The combined structural, intermolecular, electronic, and protein-binding analysis provides a detailed structure–interaction profile for this thioxoamide framework and offers a basis for its further biological investigation.