(±)-4,12,15,18,26-Pentahydroxy-13,17-dioxaheptacyclo[14.10.0.0^3,14.0^4,12.0^6,11.0^18,26.0^19,24]hexacosa-1,3(14),6(11),7,9,15,19,21,23-nonaene-5,25-dione methanol disolvate

Abstract

The title compound, C24H14O9·2CH3OH, displays a chair-shaped form. The two di­hydro­indenone ring systems are located above and below the central fused-ring system, the dihedral angles between the mean planes of di­hydro­indenone ring systems and the mean plane of central fused-ring system are 67.91 (5) and 73.52 (4)°, respectively. In the crystal, extensive O—H⋯O hydrogen bonds, weak C—H⋯O hydrogen bonds and C—H⋯π inter­actions link the mol­ecules into a three-dimensional supra­molecular architecture.

Crystal structure of (acetato-κO)(ethanol-κO)[(9S,17S,21S,29S)-9,17,21,29-tetrahydroxy-18,30-dioxaoctacyclo[18.10.0.02,7.08,19.09,17.011,16.021,29.023,28]triaconta-1,3,5,7,11(16),12,14,19,23(28),24,26-undecaene-10,22-dione-κ3O18,O21,O22]caesium ethanol monosolvate

“…Since then, the reaction has been thoroughly explored by our group, expanding the family of these ligands, which we have named vasarenes (Almog et al, 2009;Gil et al, 2014;Bengiat et al, 2016c,d). A comprehensive study of the supramolecular reactions of the vasarenes and their analogues with M + F À salts has also been carried out (Almog et al, 2012;Bengiat et al, 2016a,b,c).…”

Selective recognition of fluoride salts by vasarenes: a key role of a self-assembled in situ dimeric entity via an exceptionally short [O–H–O]− H-bond

“…1 Analogous compounds are readily prepared by reacting ninhydrin with other polyhydroxy aromatics. [2][3][4] Previous work by our group 5 has revealed the special affinity of vasarene towards compounds of the type M + F − (MF), where M is a large monovalent cation. As a ligand, it was able to solubilize the fluoride salts in organic solvents as well as binding and precipitating them as ion-pair•vasarene adducts by a non-ditopic mechanism.…”

“…5 Intrigued by the potential of this uncommon reaction, both from theoretical and practical aspects, we began to investigate the driving force for this process. Several analogues were prepared by replacing the phloroglucinol with other polyhydroxybenzenes: 1,3-benzenediol (resorcinol), 1,2-benzenediol (catechol), 1,2,3-benzenetriol ( pyrogallol), 3 and 1,2,4,5benzenetetrol. Their reactions with various ion-pairs, fluorides and others have been studied.…”