Sulfonate pseudohalides of boron subphthalocyanine

The crystal structures of three sulfonate pseudohalide derivatives of boron subphthalocyanine (BsubPc) are described and compared with four structures of three published sulfonate derivatives. Benzenesulfonate boron subphthalocyanine (benzenesulfonato)(subphthalocyaninato)boron, C₃₀H₁₇BN₆O₃S, (I)] crystallizes in the space group P with Z = 2. The structure contains two centrosymmetric π‐stacking interactions between the concave faces of the isoindoline units in the BsubPc ligands. 3‐Nitrobenzenesulfonate boron subphthalocyanine (3‐nitrobenzenesulfonato)(subphthalocyaninato)boron, C₃₀H₁₆BN₇O₅S, (II)] crystallizes in the space group P2₁/c with Z = 4. The structure contains an intermolecular S—O...π interaction from the sulfonate group to a five‐membered N‐containing ring of an isoindoline unit on the concave side of a neighbouring BsubPc ligand, at a distance of 3.151 (3) Å. The crystal of methanesulfonate boron subphthalocyanine (methanesulfonato)(subphthalocyaninato)boron, C₂₅H₁₅BN₆O₃S, (III)] was produced via sublimation and it is not a solvate, in contrast with two previously published structures of the same compound. Compound (III) crystallizes in the space group P2₁/n with Z = 2, and its structure is similar to that of the more common compound Cl‐BsubPc.