Ml. Glowka et al., CRYSTAL-STRUCTURE OF THE KETO-ENAMINE FORM OF (-(2-HYDROXYBENZYLIDENE)AMINE-L-PHENYL-L,3 PROPALLEDIOL()(1S,2S)2), Journal of chemical crystallography, 26(1), 1996, pp. 47-51
The title compound crystallizes in the orthorhombic space group P2(1)2
(1)2(1), With Z = 4, a = 6.068(1)Angstrom, b = 10.922(1)Angstrom, and
c = 21.713(2)Angstrom. The compound is the chiral ligand of a copper c
omplex used as an enantioselective catalyst. It crystallizes from meth
anol in the keto-enamine form, though the enol-imine isomer predominat
es in the solution. Most N-salicylideneamines studied by X-ray are eno
l-imines. The two tautomeric forms may interchange through an intramol
ecular hydrogen bond and the distances between non-II atoms in the res
ulting cyclic -O-H ... N=C-C=C- or -C=O ... H-N-C=C- fragment may be m
isleading, so that H atom position is the crucial factor for determina
tion of the proper tautomeric form.