p-Nitrophenyl[36]trithianonaphyrin(1.0.0.1.0.0.1.0.0) with a Weak Antiaromatic Character

Abstract

p-Nitrophenyl[36]trithiononaphyrin(1.0.0.1.0.0.1.0.0), C₇₅H₆₉N₉O₆S₃, was isolated. The crystal structure was determined by single-crystal X-ray diffraction at 200(2)K and belonged to the monoclinic space group Cc. The lattice parameters are a = 24.986(4)Å, b = 23.548(4)Å, c = 13.762(7)Å, β = 101.358(2)°, V = 7939(2)ų, Dx = 1.078 g/cm³, and Z = 4; R1 [I > 2σ(I)] and wR2 are 0.0656 and 0.1368, respectively, for 17971 independent reflections. The results of a ¹H NMR study suggested that the title compound has a weak antiaromatic character because of a slight distortion of its large macrocyclic ring, as determined by single-crystal X-ray analysis. Single-crystal X-ray analysis also revealed that the 2,5-substituted thiophene rings are inverted in the title compound.