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A highly selective recognition of fluoride was achieved through the design of a small hemicryptophane cage (3) presenting a southern tris-urea hosting moiety. The resulting host-guest complex has been characterized by electrospray ionization-high-resolution mass spectrometry, 1H and 19F NMR, and X-ray diffraction techniques. In particular, X-ray diffraction analysis of [3·F-] reveals that the encapsulation of one fluoride, within 3, occurs through NH···F- H-bonding with the six NH residues of the tris-urea ligand. An association constant