Solid Inclusion Compounds of Chiral Roof-Shaped Diamide Hosts

The hydrogen-bond-directed inclusion properties of two related enantiomerically pure diamide-type hosts have been investigated. The (11S,12S)-trans-N,N'-dicyclohexyl-9,10-dihydro-9,10- ethanoanthracene-11,12-dicarboxamide host, C₃₀H₃₆O₂N₂, (I), formed a quaternary compound when crystallized from a dimethylformamide solution and includes cyclohexylamine and HCl as guests [(I).DMF.cyclohexylamine.HCl 1:1:1:1], C₃₀H₃₆N₂O₂.C₆H₁₄N¹⁺.C₃H₇NO.Cl^-, (Ia). Three-component crystals were grown from a dimethyl sulphoxide solution of the 11S,12S-trans-N,N'-di-tert-butyl-9,10-dihydro-9,10-ethanoanthracene-11,12- dicarboxamide host, C₂₆H₃₂O₂N₂, (II), also containing H₂O as a guest [(II).DMSO.H₂O 1:2:1], C₂₆H₃₂N₂O₂.2C₂H₆OS.H₂O, (IIb). Infinite supramolecular frameworks in both compounds are created involving host and guest molecules in a way that not only host-guest, but guest-guest hydrogen-bonding interactions are observed. However, no direct host-host hydrogen bonds were formed between the chiral diamide molecules (I) or (II).

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