A new square-shaped macrocyclic amide was prepared from N-(4-amino-2-nitrophenyl)proline (ANPP). The two enantiomers of ANPP were connected in an alternating sequence and then cyclized to the corresponding macrocyclic tetramer with S-4 symmetry. In this design, there is a central cavity approximately 7 angstrom in diameter and rigid aromatic rings and intramolecular hydrogen bonding help to reduce the conformational flexibility of the molecule.