Non-Planar Lithium-Phthalocyanine in the Double Salt (nBu4N)2[Lipc]PF6

We report the synthesis of the diamagnetic double salt bis(tetra(n-butyl)ammonium) phthalocyanato(2-)lithate hexafluorophosphate (nBu4N)2[Lipc]PF6 [pc = phthalocyanine, nBu4N+ = tetra(n-butyl)ammonium] in dme (dme = dimethoxyethane). According to single-crystal X-ray diffraction structure analysis [P$\bar{1}$, a = 8.642(2) angstrom, b = 12.820(3) angstrom, c = 15.019(3) angstrom, a = 83.01(3)degrees, beta = 87.87(3)degrees, ? = 74.45(3)degrees, Z = 1, R1 = 6.4?%], the phthalocyanine building bloc shows a substantial distortion of the macrocyclic ring from planarity. The deviation from D4h symmetry originates from packing effects induced by the two tetra(n-butyl)ammonium cations located above and below the macrocycle. DFT structure optimization starting from the experimental non-planar configuration produces a fully planar complex anion [Lipc].