Crystal structure of {(but-3-en-1-yl)bis-[(pyridin-2-yl)meth-yl]amine-κ(3) N,N',N''}di-chlorido-copper(II) diethyl ether hemisolvate.

Katherine A Bussey,Margaret E Mraz,Tomislav Pintauer,Annie R Mcglone,Allen G Oliver,Jennifer R Connell,Kayode D Oshin

doi:10.1107/s2056989015003448

Abstract

The five-coordinate Cu(II) atom in the title complex [CuCl2(C16H19N3)]·0.5C4H10O, adopts a near-ideal square-pyramidal geometry (τ-5 = 0.01). The apical Cu-Cl distance is 0.2626 (6) Å longer than the basal Cu-Cl distance. Weak C-H⋯Cl interactions between pyridine rings and the Cl atoms of adjacent complex molecules are present. The solvent molecule, located on a twofold rotation axis, is situated in the voids of this arrangement. Copper atoms coordinated by tridentate nitro-gen-containing ligands have been found to be excellent promoters of Atom Transfer Radical Addition (ATRA) reactions.

Highlights

The five-coordinate CuII atom in the title complex [CuCl2(C16H19N3)]0.5C4H10O, adopts a near-ideal square-pyramidal geometry (-5 = 0.01)
Copper atoms coordinated by tridentate nitrogen-containing ligands have been found to be excellent promoters of Atom Transfer Radical Addition (ATRA) reactions
Copper(I) complexes with tridentate and tetradentate nitrogen-based ligands are currently some of the most active multidentate ligand structures developed for use in ATRA reactions (Matyjaszewski et al, 2001)

Summary

Chemical context

Transition-metal-catalyzed Atom Transfer Radical Addition (ATRA) reactions of haloalkanes and -halocarbonyls to olefins have emerged as some of the most atom economical methods for simultaneously forming C—C and C—X bonds, leading to the production of more attractive molecules with well-defined compositions, architectures, and functionalities (Pintauer & Matyjaszewski, 2005). Copper(I) complexes with tridentate and tetradentate nitrogen-based ligands are currently some of the most active multidentate ligand structures developed for use in ATRA reactions (Matyjaszewski et al, 2001). In view of the importance of these types of complexes, we report the synthesis and structural characterization of the title compound {(but-3-en-1-yl)bis[(pyridin-2-yl)methyl]amine-3N,N0 ,N00 } dichloridocopper(II) diethyl ether hemisolvate, (I)

Structural commentary

Supramolecular features

Database survey

Synthesis and crystallization

Refinement details