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This article discusses the evaluation of a new catalyst, 3 BArF, which is a bidentate iodine(III)-based halogen-bonding (XB) donor. The crystal structure of the catalyst was analyzed and compared to a known planar bis(iodolium) catalyst, 2 BArF. The comparison showed that 2 BArF is a stronger Lewis acid than 3 BArF. In a benchmark reaction involving the activation of trans-β-nitrostyrene, 2 BArF showed approximately 13 times higher turnover frequency (TOF) than 3 BArF. These results highlight the impact of catalyst structure on the properties of bidentate iodonium(III)-based XB donors. [Extracted from the article]