The unanti-cipated oxidation of a tertiary amine in a tetra-cyclic glyoxal-cyclam condensate yielding zinc(II) coordinated to a sterically hindered amine oxide

Daniel J Hubin; Blue M Cunningham; Timothy J Hubin; Jonathan P Ebel; Jeanette A Krause; Allen G Oliver

doi:10.1107/S2056989024001889

The unanti-cipated oxidation of a tertiary amine in a tetra-cyclic glyoxal-cyclam condensate yielding zinc(II) coordinated to a sterically hindered amine oxide

Acta Crystallogr E Crystallogr Commun. 2024 Mar 6;80(Pt 4):343-346. doi: 10.1107/S2056989024001889. eCollection 2024 Mar 1.

Authors

Daniel J Hubin¹, Blue M Cunningham¹, Timothy J Hubin¹, Jonathan P Ebel¹, Jeanette A Krause², Allen G Oliver³

Affiliations

¹ Department of Chemistry & Physics, Southwestern Oklahoma State University, Weatherford, OK 73096, USA.
² Department of Chemistry, University of Cincinnati, Cincinnati, OH 45221, USA.
³ Department of Chemistry & Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.

Abstract

The complex, tri-chlorido-(1,4,11-tri-aza-8-azonia-tetra-cyclo-[6.6.2.0^4,16.0^11,15]hexa-decane 1-oxide-κO)zinc(II) monohydrate, [ZnCl₃(C₁₂H₂₃N₄O)]·H₂O, (I), has monoclinic symmetry (space group P2₁/n) at 120 K. The zinc(II) center adopts a slightly distorted tetra-hedral coordination geometry and is coordinated by three chlorine atoms and the oxygen atom of the oxidized tertiary amine of the tetra-cycle. The amine nitro-gen atom, inside the ligand cleft, is protonated and forms a hydrogen bond to the oxygen of the amine oxide. Additional hydrogen-bonding inter-actions involve the protonated amine, the water solvate oxygen atom, and one of the chloro ligands.

Keywords: crystal structure; glyoxal-cyclam; zinc(II).

Grants and funding

Funding for this research was provided by: National Science Foundation, Office of the Director (grant No. OIA-194093); American Chemical Society Petroleum Research Fund.