Role of the Molecular Conformation in the Two- and Three-Dimensional Supramolecular Structure of 10 Hydroxyl-<i>N</i>-alkylamides

Sixteen new 7,7-dialkyl-5-hydroxymethyl-6-oxabicyclo[3.2.1]octane-1-carboxylic acid amide derivatives with the hydroxymethyl and the N-alkylamide functional groups in axial positions have been synthesized, and the solid-state structure of 10 of them has been determined. All of them crystallized as anhydrous compounds, and the conformation of the hydroxyl and N-alkylamide substituents was found to be correlated with the types of interactions in which they are involved, generating two- and three-dimensional hydrogen-bonding networks based on identical dimeric substructures in 8 of the 10 cases. This dimer can be considered as a supramolecular synthon for future crystal engineering studies.