Synthesis and structure of clozapine N-oxide hemi(hydro-chloride): an infinite hydrogen-bonded poly[n]catenane

The structure of the title compound, 2C₁₈H₁₉ClN₄O·HCl or (CNO)₂·HCl (C₃₆H₃₉Cl₃N₈O₂), at 100 K has tetra-gonal (I4/m) symmetry. The dihedral angle between the benzene rings of the fused ring system of the CNO mol-ecule is 40.08 (6)° and the equivalent angle between the seven-membered ring and its pendant N-oxide ring is 31.14 (7)°. The structure contains a very strong, symmetrical O-H⋯O hydrogen bond [O⋯O = 2.434 (2) Å] between two equivalent R ₃N⁺-O^- moieties, which share a proton lying on a crystallographic twofold rotation axis. These units then form a (CNO)₄·(HCl)₂ ring by way of two equivalent N-H⋯Cl hydrogen bonds (Cl^- site symmetry m). These rings are catenated into infinite chains propagating along the c-axis direction by way of shape complementarity and directional C-H⋯N and C-H⋯π inter-actions.