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Inclusion complexes of the natural product gossypol. Strong influence of the guest on the host structure in channel-type isostructural inclusion complexes of gossypol

Abstract

The crystal structures of 1 : 1 inclusion complexes of gossypol with tetrahydrofuran (GPTHF), cyclohexanone (GPCHN) and butanal (GPBTA) have been determined by X-ray structure analysis. The crystals of GPTHF are triclinic, space group PĪ,a = 10.788(2),b = 10.979(3),c = 13,880(2) Å, α = 80. 11(2), β = 103.87(1), γ = 77.96(2)°,V = 1517.8(6) Å3,Z = 2,R = 0.052 for 2701 observed reflections. The crystals of GPCHN are triclinic, space groups PĪ,a = 10.803(4),b = 11.157(5),c = 15.428(6) Å, α = 108.75(3), β = 106.93(3), γ = 103.34(3)°,V = 1573(1) Å3,Z = 2,R = 0.071 for 1879 observed reflections. The crystals of GPBTA are triclinic, space group PĪ,a = 10.190(2),b = 11.335(1),c = 14.665(2) Å, α = 73.04(1), β = 103.74(1), γ = 81.07(1)°,V = 1529.9(5) Å3,Z = 2,R = 0.068 for 2964 observed reflections. Crystal data for another 13 isostructural inclusion complexes are given.[/p]

In this isostructural group of complexes guest molecules are accommodated in channels and are hydrogen bonded to the host molecules via an 0(1)-H....O(1′) hydrogen bond. The molecular association changes significantly with the shape and size of the guest component. In GPTHF centrosymmetric dimers of gossypol formedvia O(5)-H...O(3) hydrogen bonds are associated in columns via a weak O(4)-H...O(8) hydrogen bond. In GPCHN the latter bond disappears as the distance O(4)-O(8) is increased to 3.73 Å. In GPBTA the O(5)-H...O(3) bond is replaced by three centre hydrogen bonds O(5)-H...O(2) and O(3)-H...O(5), and a centrosymmetric dimer of a new type is formed. These dimers are further connected by two weak hydrogen bonds to form columns. The butanal molecule interacts with the host structure via two hydrogen bonds. This indicates that a guest component can activate or deactivate different functional groups of the host in channel inclusion complexes of gossypol for hydrogen bond formation.

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Ibragimov, B.T., Gdaniec, M. & Dadabaev, B.N. Inclusion complexes of the natural product gossypol. Strong influence of the guest on the host structure in channel-type isostructural inclusion complexes of gossypol. J Incl Phenom Macrocycl Chem 8, 333–348 (1990). https://doi.org/10.1007/BF01041889

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Key words

  • crystal structure
  • X-ray crystallography
  • gossypol inclusion complexes