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.