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The crystal structures of three clozapinium salts: different mol-ecular configurations, and supra-molecular assembly in one, two and three dimensions.

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 ?-? 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.

SUBMITTER: Kaur M

PROVIDER: S-EPMC4438793 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:The syntheses and structures of five mol-ecular salts of protonated 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine (C11H19N2S+) with different deprotonated carb-oxy-lic acids (4-methyl-benzoic acid, 4-bromo-benzoic acid, 3,5-di-nitro-benzoic acid, fumaric acid and succinic acid) are reported, namely 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-methyl-benzoate, C11H19N2S+·C8H7O2 -, (I), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-bromo-benzoate, C11H19N2S+·C7H4BrO2 -, (II), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 3,5-di-nitro-benzoate, C11H19N2S+·C7H3N2O6 -, (III), bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) fumarate, 2C11H19N2S+·C4H2O4 2-,(IV), and the 1:1 co-crystal of bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) succinate and 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium hydrogen succin-ate 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine, 1.5C11H19N2S+·0.5C4H4O4 2-·0.5C4H5O4 -. 0.5C11H18N2S, (V). In every case, the cation protonation occurs at the N atom of the thia-zole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methyl-ene groups are disordered over two sets of sites). The C-N bond lengths of the nominal -NH+=C-NH2 fragment of the cation are indistinguishable, indicating a significant contribution of the -NH-C=N+H2 resonance form to the structure. The packing for (I)-(V) features a robust local R 2 2(8) loop motif in which the cation forms two near-linear N-H?O hydrogen bonds from the N+-H group and syn H atom of the amine group to the carboxyl-ate group of an adjacent anion [(V) shows disorder of one of these bonds over N-H?O and N?H-O contributors but the same R 2 2(8) loop results for both disorder components]. The anti H atom of the -NH2 group also forms an N-H?O hydrogen bond, which results in [001] chains in (I) and (II), isolated centrosymmetric tetra-mers in (III) and [100] chains in (IV) and (V). Hirshfeld fingerprint plots and contact percentages for the different types of contacts of the cations are discussed.

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The crystal structures of three clozapinium salts: different mol-ecular configurations, and supra-molecular assembly in one, two and three dimensions.

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