CRYSTAL-STRUCTURE OF THE PRODUCT OF A CONDENSATION REACTION OF (+ -)-GOSSYPOL WITH (R)-(+)-1-PHENYLETHYLAMINE - WHY DO DIASTEREOISOMERIC DIAMINOGOSSYPOLS COCRYSTALLIZE/
M. Gdaniec, CRYSTAL-STRUCTURE OF THE PRODUCT OF A CONDENSATION REACTION OF (+ -)-GOSSYPOL WITH (R)-(+)-1-PHENYLETHYLAMINE - WHY DO DIASTEREOISOMERIC DIAMINOGOSSYPOLS COCRYSTALLIZE/, Journal of inclusion phenomena and molecular recognition in chemistry, 17(4), 1994, pp. 365-376
The crystal structure of a compound obtained in a condensation reactio
n of (+/-)-gossypol with (R)-(+)-phenylethylamine has been determined
by X-ray structure analysis. The crystals of C46H48O6N2 . (C4H8O2)2 ar
e monoclinic, space group P2(1), a = 21.243(3), b = 8.666(1), c = 28.6
51(4) angstrom, beta = 108.24(1)-degree, V = 5009(3) angstrom3, Z = 4,
D(x) = 1.195 g cm-3, mu(Cu K(alpha))=0.66 mm-1, T = 292 K. The struct
ure has been solved by direct methods and refined to the final R value
of 0.091 for 4290 observed reflections and 1049 parameters. There are
two diastereoisomeric molecules of the host and four solvent molecule
s in the asymmetric unit. The host molecules are H-bonded into chains
with diastereoisomeric molecules alternating along the chain. The fact
that the host prefers the association mode in which molecules with a
different configuration of the 2,2'-binaphthyl moiety are H-bonded exp
lains why separation of diastereoisomeric diaminogossypols by fraction
al crystallization has been unsuccessful. The 1,4-dioxane molecules ar
e accommodated in infinite channels but only every second guest molecu
le in a channel is H-bonded to the host.