Non-mesogenic crystal structure of a synthetic 1-d-glucosamide bolaamphiphile

The crystal structure of the synthetic 1-glucosamide bolaamphiphile, N,N′-bis(β-d-glucopyranosyl)undecane-1,11-dicarboxamide (1) was determined by single-crystal X-ray analysis. The space group is P21, with cell dimensions: a = 6.220(1), b = 48.25(1), c = 4.922(2) Å, β = 105.67(2)°, and Z = 2. The glucopyranosyl ring is in a 4C1, chair conformation. The bolaamphiphile molecules are arranged in a layered structure with the alkylene chains packed antiparallel in a pleated sheet. The glucosamine moieties are linked by a three-dimensional intermolecular hydrogen-bonding network. The n-alkylene chain has an all-trans zigzag conformation with a small left-handed twist. Synthetic 1-glucosamide bolaamphiphile self-assembled to form a head-to-head layered structure with an all-trans, n-alkylene link, which was stabilize by three dimensional hydrogen-bonding network.