Gossypol (Gp), the natural product of a polyphenolic nature, is known to form a large variety of inclusion compounds with solvent molecules as the guest components.From aprotic solvents Gp inclusion compounds are formed that are based on the host matrix constructued from columnar Gp assemblies, that in the highest symmetrical case belong to the P12/c1 rod group [1].This group of compounds is represented by unstable Gp/CHCl 3 (1/1) inclusion compound that crystallizes in the C2/c space group with Z'=1.It has been proposed that desolvation of this compound proceeds stepwise via crystalline forms with the 4:3, 4:2 and 4:1 host:guest ratio [2].Indeed, inclusion compounds having these stoichiometries and constructed from similar host columnar aggregates were prepared when Gp was recrystallized from toluene, benzene and p-xylene, respectively.Moreover, the intermediate form of Gp/CHCl 3 inclusion compound with the 4:2 host: guest ratio was also obtained.To our surprise, when Gp was recrystallized from a mixture of solvents: CHCl 3 /benzene, CHCl 3 /toluene, CHCl 3 /p-xylene, stable ternary inclusion compounds were formed with the aromatic molecules (Ar) occupying every second centrosymmetric void in the basic Gp/CHCl 3 (1/1) matrix.These inclusion compounds have Gp/CHCl 3 /Ar ratio of 4/4/1 and crystallize in the P-1 or P2 1 /c space groups with Z'=4.Similar ternary compounds were also obtained with naphthalene or pentafluoroaniline as the third component.In turn, when Gp crystallization was performed from mixtures of CHCl 3 with o-or m-xylenes another group of ternary inclusion compounds was obtained with Gp/CHCl 3 /Ar ratio of 4/2/1 (P2 1 /c, Z' = 2).Structure of these compounds is to a large extent isostructural with the binary inclusion compound Gp/toluene (4/3), but with two symmetry independent guest sites occupied in ternary compounds by different guest components.In addition to structural studies, stability data for the ternary Gp compounds will be presented.
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