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Some biologically active organotellurium compounds exhibit inhibitory potency against cathepsin B. In this study, an alkyl derivative, viz. [CH 3 (CH 2 ) 2 C(I)=C(H)](nBu)TeI 2 ,  1 , has been structurally characterised by X-ray crystallography and shown to be coordinated within a C 2 I 2  donor set. When the stereochemically active lone pair of electrons is taken into account, a distorted trigonal bipyramidal geometry results with the iodide atoms in axial positions. Both intra- and inter-molecular Te···I interactions are also noted. If all interactions are considered, the coordination geometry is based on a Ψ-pentagonal bipyramidal geometry. An unusual feature of the structure is the curving of the functionalised C 5  chain. This feature has been explored by DFT methods and shown to arise as a result of close C–H···I interactions. A docking study (cathepsin B) was performed to understand the inhibition mechanism and to compare the new results with previous observations. Notably,  1  has the same pose exhibited by analogous biologically active compounds with aryl groups. Thus, the present study suggests that (alkyl) 2 TeX 2  compounds should also be evaluated for biological activity.

Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound