Crystal structure of {4-[10,15,20-tris-(4-meth-oxy-phen-yl)porphyrin-5-yl]benzyl 2-diazo-acetato}-zinc(II).

Daniel Carrie,Gerard Simonneaux,Thierry Roisnel

doi:10.1107/s2056989020001085

Abstract

In the title compound, [Zn(C50H36N6O5)], the ZnII cation is chelated by four pyrrole N atoms of the porphyrinate anion and coordinated by a symmetry-generated keto O atom of the diazo-ester group in a distorted square-pyramidal geometry. The mean Zn-N(pyrrole) bond length is 2.058 Å and the Zn-O(diazo-ester) bond length is 2.179 (4) Å. The zinc cation is displaced by 0.2202 (13) Å from the N4C20 mean plane of the porphyrinate anion toward the O atom; the involvement of this atom leads to a [100] polymeric chain in the crystal.

Highlights

The bond lengths from the zinc ion to the pyrrole nitrogen atoms span the range 2.046 (4)–2.073 (4) A, which is comparable with those reported in the literature (Nasri et al, 2016)
The bond lengths of the diazo group have been previously estimated from X-ray data and ab initio calculations for a series of diazocompounds
The N—N and C—N bond lengths are 1.112 (10) and 1.285 (10) A, respectively, which are close to those observed for an aromatic diazoketone [N—N =1.117 (8); C—N = 1.316 (9) A ; Yanez et al, 2003]

Summary

Structural commentary

The structure is a one-dimensional polymer, wherein the Zn2+ ion bonds to four pyrrole nitrogen atoms and to the diazo ester oxygen atom of an adjacent molecule [O60i: symmetry code: (i) x À 1, y, z], thereby defining the propagation of the chain, Figs. The bond lengths from the zinc ion to the pyrrole nitrogen atoms span the range 2.046 (4)–2.073 (4) A , which is comparable with those reported in the literature (Nasri et al, 2016). The bond lengths of the diazo group have been previously estimated from X-ray data and ab initio calculations for a series of diazocompounds (average parameters: N—N 1.1189 and N—C = 1.3263 A ). Little variance in these bond lengths occurs, even with varied functionality around the diazo moiety (Goodman et al, 1994).

Supramolecular features

Synthesis and crystallization

VENTURE Bruker AXS diffractometer

H55 C56 H56 C51 C52 H52 C53 H53 O58 C59 C57 H57A H57B O60 C61 H61 N62 N63