Abstract
The crystal structures of two substituted HATN (hexa-aza-tri-naphthyl-ene) derivatives, namely 2,3,8,9,14,15-hexa-methyl- and 2,3,8,9,14,15-hexa-phenyl-5,6,11,12,17,18- hexa-zatri-naphthyl-ene (HATNMe(6) and HATNPh(6)), are reported. Whereas the structure of the methyl-substituted derivative (HATNMe(6)) contains no solvent mol-ecules (C(30)H(24)N(6)), the hexa-phenyl-substituted structure (HATNPh(6)) contains two mol-ecules of di-chloro-methane (C(60)H(36)N(6)·2CH(2)Cl(2)). This class of planar bridging ligands is known for its electron-deficient systems and its ability to form π-π stacking inter-actions. Indeed, in both crystal structures strong π-π stacking inter-actions are observed, but with different packing features. The di-chloro-methane mol-ecules in the crystal structure of HATNPh(6) are situated in the voids and are involved in C-H⋯N contacts to the nitro-gen atoms of the pyrazine units.