The crystal structure of fluphenazinium dipicrate dimethylsulphoxide solvate

The title compound, C22H28F3N3OS2+ × 2(C6H2N3O7−) × (CH3)2SO---the picrate salt of the potent antipsychotic drug, fluphenazine---crystallizes in the triclinic P-1 space group with unit cell parameters a = 10.6333(12) Å, b = 11.9696(12) Å, c = 17.7036(15) Å, α = 103.265(9)°, β = 98.414(9)°, γ = 102.702(10)°. The ionic fragments: the fluphenazinium dictation, and two picrate anions, are joined by means of strong N--H···O and weak C--H···O hydrogen bonds into the chains of alternating cations and anions, expanding along 010 direction. Within the chain, the picrates interact by means of short $\pi${\textperiodcentered}{\textperiodcentered}{\textperiodcentered}$\pi$ interactions: the mean distance between the planes is 3.366 {\AA}; additional interaction of the same type between one of the picrates and the phenyl ring of the phenothiazine ring system additionally strengthen the pattern. The phenothiazine ring exists in a typical, ``butterfly-like'' conformation, with two terminal rings planar and the central ring in a slightly flattened boat form. This conformation results in the dihedral angle between the terminal rings of 41.76(5){\textdegree}. The aliphatic chain which substitutes phenothiazine at N-position is not in an extended conformation, the torsion angles along this chain are 75.95(14){\textdegree} and −163.96(10){\textdegree}. The structure contains also the solvent---dimethylsulphoxide molecules, which are connected with the cation--anion structure by means of strong O--H{\textperiodcentered}{\textperiodcentered}{\textperiodcentered}O hydrogen bonds