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While the spectra of the smallest azacryptand with <jats:italic>p<\/jats:italic>\u2010phenyl linkers and its elongated derivative with <jats:italic>p<\/jats:italic>\u2010biphenyls linker were found to match well with the computed spectra, the computed conformational preferences of the <jats:italic>m<\/jats:italic>\u2010biphenyl\u2010based azacryptand did not seem to reflect the conformations dominating in chloroform solution. A detailed analysis revealed that structural changes resulting in a collapsed cage structure gave a notably better match with the experiment. It could subsequently be concluded from the VCD analysis, that the octaazacryptands prefer a collapsed structure, which is not predicted by density functional theory (DFT) calculations as the global minimum structures. 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