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

Autor: van der Peet PL; School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, 3010, Australia., Joyce RD; Advanced Molecular Technologies, Unit 1, 7-11 Rocco Drive, Scoresby, Victoria, 3179, Australia., Ott H; Bruker AXS GmbH, Oestliche Rheinbrueckenstr. 49, 76187 Karlsruhe, Germany., Marcuccio SM; Advanced Molecular Technologies, Unit 1, 7-11 Rocco Drive, Scoresby, Victoria, 3179, Australia., White JM; School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, 3010, Australia., Williams SJ; School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, 3010, Australia.
Jazyk: angličtina
Zdroj: Acta crystallographica. Section E, Crystallographic communications [Acta Crystallogr E Crystallogr Commun] 2022 Sep 27; Vol. 78 (Pt 10), pp. 1056-1060. Date of Electronic Publication: 2022 Sep 27 (Print Publication: 2022).
DOI: 10.1107/S2056989022009306
Abstrakt: The structure of the title compound, 2C 18 H 19 ClN 4 O·HCl or (CNO) 2 ·HCl (C 36 H 39 Cl 3 N 8 O 2 ), at 100 K has tetra-gonal ( I 4/ 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 3 N + -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.
(© Peet et al. 2022.)
Databáze: MEDLINE
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