Synthesis of distorted molecules based on spatial control with icosahedral carboranes

In the crystal structure of 1,2-bis(o-carboranyl)benzene (1), the benzene ring is remarkably twisted out of planarity, owing to the steric bulkiness of two adjacent carboranyl groups. In the carboracycle (2), the two benzene rings are slantingly stacked owing to spatial control by the carborane cages.