Crystal and molecular structure of N-(n-octyl)-6-deoxy-d-gluconamide: a novel packing of amphiphilic molecules

N-(n-Octyl)-6-deoxy-d-gluconamide crystallizes in the orthorhombic space group P212121, with a = 5.4524(5), b = 16.662(3), and c = 36.897(5) Å. The structure was determined by X-ray diffraction and refined to R = 9.2%. The asymmetric crystal unit contains two molecules (A,B) with significantly different conformations. In contrast to the crystal structures of the N-(n-alkyl)-d-gluconamide family, in which the molecules were found arranged in head-to-tail monolayers, molecules A and B form a complex motif with pairwise alternating orientations and interdigitating antiparallel aliphatic chains. The two symmetry independent molecules form considerably different hydrogen bond patterns.