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X-ray analysis revealed the crystal structure of the synthetic sugar-based bolaamphiphile, N, N'-bis(beta-D-glucopyranosyl)undecane-1, 11-dicarboxamide (1), in which two D-glucose units were linked by beta-N-glycosidic bond to 1, 11-undecane dicarboxylic acid. This molecule self-assembled to give a platelet crystal in water. The crystal packing pattern showed a layered structure where their alkylene chains were arranged in a pleated sheet. Each direction of the molecular packing was antiparallel. These arrangements were stabilized by hydrogen-bonding networks of amide groups and sugar hydroxy groups. Intra-layer hydrogen bondings were found between the amide groups involving O-2-H hydroxy groups with a translation motif. Inter- and intra-layer hydrogen-bonding networks of the sugar hydroxy groups were also found in the equatorial direction of the pyranose rings.
Crystal data; C25H46N2O12, monoclinic P21, a = 6.220(1), b = 48.25(1), c = 4.922(2) , beta = 105.67(2), V = 1422.3(6) 3, Z = 2, RF = 0.0503 and RWF = 0.0782 for 2256 observed [F > 3sigma (F) ] reflections.
