Abstract
The structures of three salts derived from clozapine, 8-chloro-11-(4-methyl-piperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine, are reported, namely, clo-za-pin-ium 3,5-di-nitro-benzoate dimethyl sulfoxide monosolvate, C18H20ClN4 (+)·C7H3N2O6 (-)·C2H6OS, (I), where the dimethyl sulfoxide component is disordered over two sets of atomic sites having occupancies 0.627 (2) and 0.373 (2); clo-za-pin-ium hydrogen maleate 0.21-hydrate, C18H20ClN4 (+)·C4H3O4 (-)·0.21H2O, (II), and clozapinium 2-hy-droxy-benzoate, C18H20ClN4 (+)·C7H5O3 (-), (III). In all three salts, the protonation site is the methyl-ated N atom of the piperazine ring, and the dimensions and conformations of the fused tricyclic system are very similar. However, differences are apparent in the piperazine component: in both compounds (II) and (III), the unprotonated N atom of this ring has a pyramidal geometry, but in compound (I) this atom has a planar geometry. In compound (III), both N-substituents in this ring occupy equatorial sites, but in compound (II) the fused tricyclic system occupies an axial site of the piperazine ring. The independent components of compound (I) are linked within the selected asymmetric unit by a combination of N-H⋯O and C-H⋯O hydrogen bonds, and these hydrogen-bonded aggregates are linked into chains by an aromatic π-π stacking inter-action. In compound (II), the components are linked into sheets by a combination of O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, and in compound (III), a combination of N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonds links the components into a three-dimensional framework structure. Comparisons are made with some similar compounds.
Highlights
The crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensions
The structures of three salts derived from clozapine, 8-chloro-11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine, are reported, namely, clozapinium 3,5-dinitrobenzoate dimethyl sulfoxide monosolvate, C18H20ClN4+ÁC7H3N2O6ÀÁC2H6OS, (I), where the dimethyl sulfoxide component is disordered over two sets of atomic sites having occupancies 0.627 (2) and 0.373 (2); clozapinium hydrogen maleate 0.21-hydrate, C18H20ClN4+ÁC4H3O4ÀÁ0.21H2O, (II), and clozapinium 2-hydroxybenzoate, C18H20ClN4+ÁC7H5O3À, (III)
Differences are apparent in the piperazine component: in both compounds (II) and (III), the unprotonated N atom of this ring has a pyramidal geometry, but in compound (I) this atom has a planar geometry
Summary
8-chloro-11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine, is a well established medication used in the treatment of schizophrenia which in general leads to a lower incidence of adverse side effects such as Parkinsonian-type symptoms than some other treatments (Breier et al, 1994). Structures have been reported for both the free base itself (Petcher & Weber, 1976) and for its doubly-protonated di-cation, as the dibromide salt (Fillers & Hawkinson, 1982), there appear to be no reports of the structures of any monoprotonated clozapine derivatives. We have determined the structures of three such salts with a variety of counter-ions. Of these salts, the 3,5-dinitrobenzoate crystallizes from dimethyl sulfoxide as a stoichiometric monosolvate (I) (Fig. 1, Scheme 1); the hydrogen maleate crystallizes from the same solvent as a partial hydrate (II) (Fig. 2); doi:10.1107/S205698901500554X. The aims of the present study are firstly to establish the site of protonation in the mono-protonated cations; secondly, to compare the conformations of the clozapinium cations; and thirdly, to explore the supramolecular assembly in these three salts
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