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

7 pages, 10 figures, 4 tables, 2 charts.-- Printed version published May 2, 2007.Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Center, CCDC reference numbers 601071-601080.Crystallographic information files (CIF format) and experimental data (melting point, IR, 1H and 13C NMR, MS(EI), HRMS) for all compounds are available Open Access at: http://pubs.acs.org/doi/suppl/10.1021/cg060671u?cookieSet=1Sixteen 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.Financial support from the DGICYT of Spain through project CTQ2004-01674 is gratefully acknowledged. N.P.H. thanks the Spanish Ministry of Education for a Predoctoral Fellowship