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Title: Crystal structures of the solvates of diethylaminogossypol with ethyl acetate and pyridine

item Dowd, Michael

Submitted to: Journal of Chemical Crystallography
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 3/2/2009
Publication Date: 3/21/2009
Citation: Tilyabaev, Z.Z., Talipov, S.A., Ibragimov, B.T., Dowd, M.K., Yuldashev, A.M. 2009. Crystal structures of the solvates of diethylaminogossypol with ethyl acetate and pyridine. Journal of Chemical Crystallography. 39:677-682.

Interpretive Summary: X-ray diffraction was used to study the structures of two new crystalline solvates of diethylamino-gossypol with ethyl acetate and pyridine. Like gossypol, a natural product of the cotton plant, this compound forms complexes with low molecular weight organic molecules. With ethyl acetate, the DEAG and solvent are in a 2:1 molar ratio and with pyridine the same ratio is 2:5. The results will be of interest to scientists working to develop products based on gossypol unusual ability to form inclusion complexes with small molecular weight molecules.

Technical Abstract: The crystal structures of diethylaminogossypol with ethyl acetate (DEAG-EA) and pyridine (DEAG-P) were studied by room-temperature X-ray diffraction. The host-to-guest molecule ratio in these complexes is 2:1 for DEAG-EA and 2:5 for DEAG-P. The crystal and cell parameters for DEAG-EA are C34H40N2O6•0.5(C4H8O2), M=660.78, triclinic, space group P-1, a=11.316(2) Å, b=12.082(2) Å, c=15.085(3) Å, alpha=73.34(3)º, beta=73.32(3)º, gamma=73.61(3)º, V=1847.3(7) Å3, Z=2, and dcalc.=1.188 g/cm3 and for DEAG-P are C34H40N2O6•2.5(C5H5N), M=769.91, triclinic, space group P-1, a=9.6090(19) Å, b=14.894(3) Å, c=16.038(3) Å, alpha=90.66(3)º, beta=106.25(3)º, gamma=103.17(3)º, V=2138.7(9) Å3, Z=2, and dcalc.=1.195 g/cm3. In both structures, the diethylaminogossypol molecules are in the enamine form, which is same tautomer found for other reported Schiff’s base gossypol derivatives. The enantiomeric gossypol molecules of each structure form different centrosymmetric dimer assemblies. These assemblies pack differently in each solvate.