Crystal structures of nickel, copper and zinc naphthalocyaninates

Abstract

The crystal and molecular structures of [M(nc)](M = Ni, Cu or Zn; H₂nc = naphthalocyanine) have been determined. The bond lengths Ni–N 1.929(7), Cu–N 1.951(4) and Zn–N 1.983(4)Å are nearly consistent with those in the phthalocyaninates of the same metals. The patterns of the perpendicular displacements of atoms from the mean plane for the three molecules, although small, are identical with each other and also quite similar to those commonly observed in the β polymorphs of phthalocyanines. The three molecules pack in similar fashion. The molecules stack within the ab plane, forming a two-dimensional sheet, contrary to the one-dimensional stacking of the phthalocyaninates of the same metals. The azamethine N atoms are not in close contact with the central metal atoms of adjacent molecules, although their deviations from the mean plane are appreciable.