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  • 1
    Electronic Resource
    Electronic Resource
    Inclusion complexes of the natural product gossypol. Crystal structures of gossypol complexes with benzene and chloroform as guests (1990)
    Springer
    Journal of inclusion phenomena and macrocyclic chemistry 9 (1990), S. 231-242 
    Details
    ISSN: 1573-1111
    Keywords: Crystal structure ; X-ray crystallography ; gossypol ; inclusion complexes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The crystal structures of the lattice inclusion complexes of gossypol with benzene and chloroform have been determined by X-ray structure analysis. The crystals of (C30H30O8)2 · C6H6 (GPBNZ) are triclinic, space groupPI,a = 11.241(3),b = 14.986(4),c = 17.380(4) Å, α = 98.89(2), β = 99.86(2), γ = 98.91(2)°,V = 2800(2) Å3,Z = 2,D x = 1.32 g cm−3, μ(CuK α) = 7.35 cm−1. The structure has been refined to a finalR value of 0.050 for 6146 observed reflections. The crystals of C30H30O8·CHCl3 (GPCLF) are monoclinic, space groupC2/c,a = 28.464(4),b = 8.948(1),c = 26.480(4) Å, β = 108.93(2)°,V = 6380(2) Å3,Z = 8,D x = 1.33 g cm−3, μ(CuKα) = 30.42 cm−1. The structure has been refined to a finalR value of 0.100 for 1980 observed reflections. GPCLF forms an intercalate-type structure and GPBNZ a clathrate-type structure. There are, however, some similarities in the packing mode of the host molecules in these two structures. On a basis of comparison of the crystal packing of GPCLF and GPBNZ one can postulate that in the desorption process of the intercalate-type GPCLF complex an intermediate clathrate structure of the GPBNZ-type should be formed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01053121
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  • 2
    Electronic Resource
    Electronic Resource
    Inclusion complexes of the natural product gossypol. Crystal structure of the 1 : 1 complex of gossypol with isovaleric acid (1990)
    Springer
    Journal of inclusion phenomena and macrocyclic chemistry 8 (1990), S. 423-429 
    Details
    ISSN: 1573-1111
    Keywords: Crystal structure ; X-ray crystallography ; gossypol ; host-guest complexes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The crystal structure of the 1 : 1 lattice inclusion complex of gossypol with isovaleric acid has been determined by X-ray structure analysis. The crystals of C30H30O8⁗C5H10O2 are monoclinic, space groupC2/c,a=28.835(7),b=9.063(2),c=26.880(4)Å, β=109.66(1)°,V=6615(2) Å3,Z=8,D x = 1.25 g cm−3, μ(CuKα) = 7.14 cm−1,T = 295 K. The structure was solved by direct methods and refined with isotropic thermal parameters to the finalR value of 0.132 for 1114 observed reflections. Hydrogen bonded gossypol molecules form columns along the [1 0 1] direction. These columns pack into layers parallel to the (101) plane. The layers of gossypol molecules are separated by the layers of isovaleric acid. The acid molecules are connectedvia a pair of O-H...O hydrogen bonds forming centrosymmetric dimers. There is no hydrogen bond interaction between the carboxylic acid dimers and gossypol molecules.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01041198
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  • 3
    Electronic Resource
    Electronic Resource
    Inclusion complexes of the natural product gossypol. Crystal structure of the 2:1 complex of gossypol with amyl acrylate (1990)
    Springer
    Journal of inclusion phenomena and macrocyclic chemistry 8 (1990), S. 431-438 
    Details
    ISSN: 1573-1111
    Keywords: Crystal structure ; X-ray crystallography ; gossypol ; inclusion complexes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The crystal structure of the 2: 1 inclusion complex of gossypol with amyl acrylate has been determined by X-ray structure analysis. The crystals of (C30H30O8)2⁗C8H14O2 are triclinic, space group P $$\bar 1$$ ,a = 14.425(2),b = 15.519(1),c = 16.409(2) Å, α =97.89(1), β = 117.80(1), γ =67.01(1)° (reduced cell:a = 14.425(2),b = 15.519(2),c = 16.017(2)Å, α = 92.19(1), β = 115.01(l), γ =67.01(1)°],V = 2986.7(5) Å3,Z = 2,D x = 1.31 g cm−3, μ(CuK α) = 7.40 cm−1,T = 292 K. The structure has been solved by direct methods and refined to the final R value of 0.059 for 5155 observed reflections. The gossypol molecules bonded via several hydrogen bonds form centrosymmetric tetramers. The two independent gossypol molecules, A and B, are related within the tetramer by a local noncrystallographic 2-fold axis. The host molecules in the crystal form cavities in which two guest molecules are placed. The ester molecule interacts via a pair of C-...H-O hydrogen bonds with two gossypol molecules of the same chirality and belonging to the same tetramer unit. The amyloxy group of the ester molecule shows a very large thermal motion. It adopts a non-extended conformation in which it can be fitted into the cavity formed by the host molecules.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01041199
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  • 4
    Electronic Resource
    Electronic Resource
    Inclusion complexes of the natural product gossypol. Clathrate type inclusion complexes of gossypol with carbonyl group containing guests (1990)
    Springer
    Journal of inclusion phenomena and macrocyclic chemistry 8 (1990), S. 409-421 
    Details
    ISSN: 1573-1111
    Keywords: Crystal structure ; X-ray crystallography ; gossypol ; inclusion complexes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The crystal structures of 2:1 inclusion complexes of gossypol with methyl propionate (GPMEP) and ethyl acetoacetate (GPEAA) have been determined by X-ray structure analysis. The crystals of GPMEP, C30H30O8⁗l/2 C4H8O2, are monoclinic, space groupC2/c,a=11.079(3),b = 30.724(7), c = 16.515(5) Å, β = 90.46(2)°,V = 5621(3) Å,Z = 8,D x = 1.33 g cm−3. The structure has been refined to the finalR value of 0.059 for 1899 observed reflections. The crystals of GPEAA, C30H30O8⁗l/2 C6H10O3, are monoclinic, space groupC2/c,a=11.095(2),b=30.604(9),c = 16.955(5) Å, β = 88.27(2)°,V = 5754(3) Å,Z = 8,D x = 1.35 g cm−3. The structure has been refined to the finalR value of 0.056 for 2502 observed reflections. In contrast to previously investigated inclusion complexes of gossypol the host molecules do not form centrosymmetric dimersvia hydrogen bonds. In the crystal structures the racemic gossypol is separated into enantiomers forming alternating bimolecular layers. Nearly perpendicular to these chiral bilayers run elongated cavities enclosed on each side by layers of opposite chirality. The surface of these layers is hydrophobic, the polar groups are hidden inside the layer. Guest molecules which are hydrogen bonded to the host are included in cylindrically shaped cavities. Possible hydrogen bonds between host and guest are analysed for this isostructural class of complexes.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01041197
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