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

Article abstract of DOI:10.1016/0008-6215(94)00346-H

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) Angstroem.The structure was determined by X-ray diffraction and refined to R = 9.2percent.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 andinterdigitating antiparallel aliphatic chains.The two symmetry independent molecules form considerably different hydrogen bond patterns.Keywords: Alkyl-gluconamides; Amphiphilic molecules; Aliphatic chain packing; Crystal packing; Hydrogen bonding