
%0 Journal Article
%A Ahn,, Paul D. 
%A Bishop,, Roger 
%A Craig, Donald C. 
%A Downing, Gary A. 
%A Scudder, Marcia L. 
%T Systematic Structural Modification of a Pentacyclic Helical Tubuland Host Diol
%J Australian Journal of Chemistry
%D 1998/01/13
%V 50
%N 11
%P 1053-1060
%K 
%R https://doi.org/10.1071/C97073
%U https://www.publish.csiro.au/paper/C97073 
%X Reaction of methylmagnesium chloride and pentacyclo&#91;7.3.0.0 2,7.0 3,11 .0 6,10 &#93;dodecane-8,12-dione (4) yields the C2-symmetric diol (5) (62%) and the unsymmetrical diol (6) (36%) whose crystal structures are analysed in crystal engineering terms. The former isomer is the tenth member of the helical tubuland diol family, crystallizing in space groupP 3121 as a microporous lattice containing empty parallel canals with 9&#183; 9&#197;2cross-sectional area. Molecules of diol (6) hydrogen bond through (-O-H)4 cycles to form layers which stack in space group P 21/c by means of hydrocarbon dispersion forces. Diol (7), the bis(trifluoromethyl) analogue of (5), does not form a helical tubuland lattice. The structure of its hemihydrate also contains (&#8211;O&#8211;H)4 cycles but here the second diol hydroxy group hydrogen bonds to water resulting in a network structure in space group P-421c. 
