Treatment of the ortho-tri­aza­cyclo­phane 1,4-di­methyl­tribenzo[b,e,h][1,4,7]tri­aza­cyclo­nona-2,5,8-triene [(C6H5)3(NH)(NCH3)2, L1] with Fe[N(SiMe3)2]2 yields the dimeric iron(II) complex bis­(μ-1,4-di­methyl­tribenzo[b,e,h][1,4,7]tri­aza­cyclo­nona-2,5,8-trien-7-ido)bis­[(μ-1,4-di­methyl­tribenzo[b,e,h][1,4,7]tri­aza­cyclo­nona-2,5,8-trien-7-ido)iron(II)], [Fe(C20H18N3)4] or Fe2(L1)4 (9). Dissolution of 9 in tetra­hydro­furan (THF) results in solvation by two THF ligands and the formation of a simpler monoiron complex, namely bis­(μ-1,4-di­methyl­tribenzo[b,e,h][1,4,7]tri­aza­cyclo­nona-2,5,8-trien-7-ido-κN7)bis­(tetra­hydro­furan-κO)iron(II), [Fe(C20H18N3)2(C4H8O)2] or (L1)2Fe(THF)2 (10). The reaction is reversible and 10 reverts in vacuo to diiron complex 9. In the structures of both 9 and 10, the monoanionic tri­aza­cyclo­phane ligand L1− is observed in only the less-symmetric saddle conformation. No bowl-shaped crown conformers are observed in the solid state, thus preventing chelating κ3-coordination to the metal as had been proposed earlier based on density functional theory (DFT) calculations. Instead, the L1− ligands are bound in either a η2-chelating fashion through the amide and one amine donor (for one of the four ligands of 9), or solely through their amide N atoms in an even simpler monodentate η1-coordination mode. Density functional calculations on dimer 9 revealed nearly full cationic charges on each Fe atom and no bonding inter­action between the two metal centers, consistent with the relatively long FeFe distance of 2.912 (1) Å observed in the solid state.