Density functional theory calculations were used to design an anion receptor that utilizes antimony(III) secondary bonding interactions. Calculations were performed on promising motifs found in the chemical literature where two antimony sites were found in close proximity to a halide anion. The study was extended to a structurally related class of 1,3,2-benzodioxastibole derivatives to elucidate their potential Binding Site for binding halide ions. Multiple geometric conformations were evaluated and various ratios of halide anions were considered. According to the computation results, this class of anion receptors shows strong affinities toward charge-dense halides. These 1,3,2-benzodioxastibole derivatives were prepared to evaluate their synthetic accessibility. Structural characterization of one species revealed the ability to bind up to three electron donors through secondary bonding interactions. This gates the future experimental study of these antimony systems for anion binding and recognition.