By virtue of their three-fold axis of symmetry, hexaazatriphenylene (HAT) molecules are well suited to macromolecular research efforts. Our goal was to design and prepare a HAT based molecular receptor from the hexaaminobenzene, alpha-dione condensation approach reported by Khone and Praefcke. The novel strategy employed in this work was use of a meta-nitro substituted benzil in the HAT condensation reaction. Over three synthetic steps, hexakis (3-benzamidophenyl) –1,4,5,8,9,12-hexaazatriphenylene (33) was isolated in analytically pure form. The NMR spectra of 33 is highly ordered suggesting C3v symmetry where the benzamide arms are all geared to one face to form a “bowl” structure. One deuterium exchangeable singlet is observed at very high field supporting the assignment of a symmetric, cyclic hydrogen bond between the six benzamide arms. The high structure pre-organization for 33, in conjunction with the synthetic methodology developed in this work, leads to unique possibilities for construction of tubular HAT macromolecules.