The crystal structure of fluphenazinium dipicrate dimethylsulphoxide solvate

Dutkiewicz, Grzegorz and Siddaraju, B. P. and Yathirajan, H. S. and Narayana, B. and Kubicki, Maciej (2010) The crystal structure of fluphenazinium dipicrate dimethylsulphoxide solvate. Journal of Chemical Crystallography, 40 (11). pp. 970-974. ISSN 1074-1542

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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.

Item Type: Article
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: LA manjunath user
Date Deposited: 05 Jul 2019 09:55
Last Modified: 05 Jul 2019 09:55

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