Abstract

In the title compound, [Fe(II)(C44H24Cl4N4)(C6H5CH2NH2)2]·C6H14 or [Fe(II)(TPP-Cl)(BzNH2)2]·n-hexane [where TPP-Cl and BzNH2 are 5,10,15,20-tetra-kis-(4-chloro-phen-yl)porphyrinate and benzyl-amine ligands, respectively], the Fe(II) cation lies on an inversion centre and is octa-hedrally coordinated by the four pyrrole N atoms of the porphyrin ligand in the equatorial plane and by two amine N atoms of the benzyl-amine ligand in the axial sites. The crystal structure also contains one inversion-symmetric n-hexane solvent mol-ecule per complex mol-ecule. The average Fe-Npyrrole bond length [1.994 (3) Å] indicates a low-spin complex. The crystal packing is sustained by N-H⋯Cl and C-H⋯Cl hydrogen-bonding inter-actions and by C-H⋯π inter-molecular inter-actions, leading to a three-dimensional network structure.

Highlights

  • In the title compound, [FeII(C44H24Cl4N4)(C6H5CH2NH2)2]C6H14 or [FeII(TPPCl)(BzNH2)2]n-hexane [where TPP-Cl and BzNH2 are 5,10,15,20-tetrakis(4chlorophenyl)porphyrinate and benzylamine ligands, respectively], the FeII cation lies on an inversion centre and is octahedrally coordinated by the four pyrrole N atoms of the porphyrin ligand in the equatorial plane and by two amine N atoms of the benzylamine ligand in the axial sites

  • It has been shown that the reaction of primary and secondary amines with iron(III) metalloporphyrins results in a basecatalysed one-electron reduction process and concomitant dissociation of the deprotonated amine radical

  • It is known that the addition of an excess of sterically unhindered alkylamines to an Fe(III) porphyrin derivative leads to bis(amine)–iron(II) porphyrins with the central metal cation in a six-coordination (Morice et al, 1998)

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Summary

Chemical context

The structure of turnip cytochrome f has been determined on the basis of X-ray measurements (Martinez et al, 1996), showing that the -amino group of the Tyr-1 entity coordinates trans to the His-25 entity in the c-type heme protein. Bisamine FeII metalloporphyrins appear to be functionally significant as models for cytochrome f. It is known that the addition of an excess of sterically unhindered alkylamines to an Fe(III) porphyrin derivative leads to bis(amine)–iron(II) porphyrins with the central metal cation in a six-coordination (Morice et al, 1998). The number of published structures of these type of iron(II) metalloporphyrins is small. We report the synthesis, the molecular and crystal structures as well as UV-spectroscopic properties of bis(benzylamine)[5,10,15,20-tetra(para-chlorophenyl)porphyrinato]iron(II)

Structural commentary
Supramolecular features
Synthesis
UV–vis spectra
Refinement
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