Multistep synthetic pathway towards a series of the anisoleboron-capped ribbed-functionalized iron(II) cage complexes was developed. Their hexachloroclathrochelate precursor was obtained by the template condensation of three dichloroglyoximate chelating ligand synthons with two molecules of 4methoxyphenylboronic acid as a Lewis-acidic cross-linking agent on the iron(II) ion as a matrix. It easily underwent a stepwise nucleophilic substitution with S 2 -and O 2 -dinucleophilic aliphatic (ethanedithiolate) or aromatic (pyrocatecholate) agents, forming the stable X 2 (X = S or O)-six-membered ribbed substituent(s) at a quasiaromatic cage framework. Performing of these reactions under the different reaction conditions (i.e., at various hexachloroclathrochelate-to-nucleophile molar ratios, a wide range of temperatures and a series of the solvents) allowed to control a predominant formation of its mono-, di-or triribbed-substituted macrobicyclic derivatives. Thus obtained iron(II) di-and tetrachloroclathrochelates can undergo their post-synthetic transformations with active nucleophilic agents. The latter complexes underwent a further nucleophilic substitution with the anionic derivative of n-butanthiol, thus giving the hexasul de macrobicyclic compound with two functionalizing n-alkyl substituents in one of its three chelate a-dioximate fragments and two apical biorelevant anisole substituents. The obtained iron(II) clathrochelates, possessing a low-spin electronic d 6 con guration, were characterized using elemental analysis, MALDI-TOF mass spectrometry, UV-vis, 1 H and 13 C{ 1 H} NMR spectroscopies, and by the singlecrystal X-ray diffraction experiments for the hexachloroclathrochelate precursor, its dichlorotetrasul de macrobicyclic derivative and the monoribbed-functionalized hexasul de cage complex. In all their molecules, the encapsulated iron(II) ion is situated in the centre of its FeN 6 -coordination polyhedron, the geometry of which is intermediate between a trigonal prism and a trigonal antiprism with the distortion angles φ from 21.4 to 23.4°. Halogen bonding between the polyhalogenoclathrochelate molecules in their crystals is observed.