Crystal structure of {(R)- N2-[(benzo[ h]quinolin-2-yl)meth-yl]- N2'-[(benzo[ h]quinolin-2-yl)methyl-idene]-1,1'-binaphthyl-2,2'-di-amine-κ4N, N', N'', N'''}(trifluoromethane-sulfonato-κ O)zinc(II)} trifluoromethane-sulfonate di-chloro-methane 1.5-solvate

Shayna R Skokan; Monica M Reeson; Kayode D Oshin; Anastasiya I Vinokur; John A Desper; Christopher J Levy

doi:10.1107/S2056989017008027

Crystal structure of {(R)- N²-[(benzo[ h]quinolin-2-yl)meth-yl]- N^2'-[(benzo[ h]quinolin-2-yl)methyl-idene]-1,1'-binaphthyl-2,2'-di-amine-κ⁴N, N', N'', N'''}(trifluoromethane-sulfonato-κ O)zinc(II)} trifluoromethane-sulfonate di-chloro-methane 1.5-solvate

Acta Crystallogr E Crystallogr Commun. 2017 Jun 2;73(Pt 7):949-953. doi: 10.1107/S2056989017008027. eCollection 2017 Jul 1.

Authors

Shayna R Skokan¹, Monica M Reeson¹, Kayode D Oshin¹, Anastasiya I Vinokur², John A Desper³, Christopher J Levy³

Affiliations

¹ Department of Chemistry, Creighton University, Omaha, NE 68102, USA.
² Department of Chemistry, University of Wisconsin, Madison, WI 53558, USA.
³ Department of Chemistry, Kansas State University, Manhattan, KS 66506, USA.

Abstract

The zinc(II) atom in the title compound, [Zn(C₄₈H₃₁N₄)(CF₃SO₃)](CF₃SO₃)·1.5CH₂Cl₂, adopts a distorted five-coordinate square-pyramidal geometry. It is coordinated by one tri-fluoro-methane-sulfonate ligand and four N atoms of the N²-[(benzo[h]quinolin-2-yl)meth-yl]-N^2'-[(benzo[h]quinolin-2-yl)methyl-idene]-1,1'-binaphthyl-2,2'-di-amine ligand. The complex is present as a single-stranded P-helimer monohelical structure incorporating π-π and/or σ-π inter-actions. One of the imine bonds present in the original ligand framework is reduced, leading to variations in bond lengths and torsion angles for each side of the ligand motif. The imine-bond reduction also affects the bond lengths involving the metal atom with the N-donor atoms located on the imine bond. There are two mol-ecules of the complex in the asymmetric unit. One of the mol-ecules exhibits positional disorder within the coordinating tri-fluoro-methane-sulfonate ion making the mol-ecules symmetric-ally non-equivalent.

Keywords: asymmetric catalysis; chiral ligand; crystal structure; five-coordinate zinc(II) complex; monohelical structure.

Grants and funding

This work was funded by Creighton University grant . Cambridge Isotope Laboratories, Inc. grant . National Science Foundation, Division of Chemistry grant CHE-0349258.