Three closely-related cyclohexanols (C35H27X2N3O3;X= F, Cl or Br): similar molecular structures but different crystal structures

摘要

Three highly-substituted cyclo­hexa­nol derivatives have been prepared from 2-acetyl­pyridine and 4-halogenobenzaldehydes under mild conditions. (1RS,2SR,3SR,4RS,5RS)-3,5-Bis(4-fluoro­phen­yl)-2,4-bis­(pyridine-2-carbon­yl)-1-(pyridin-2-yl)cy­clo­hexa­nol, C35H27F2N3O3, (I), (1RS,2SR,3SR,4RS,5RS)-3,5-bis­(4-chloro­phen­yl)-2,4-bis­(pyridine-2-carbon­yl)-1-(pyridin-2-yl)cyclo­hexa­nol acetone 0.951-solvate, C35H27Cl2N3O3·0.951C3H6O, (II), and (1RS,2SR,3SR,4RS,5RS)-3,5-bis­(4-bromo­phen­yl)-2,4-bis­(pyridine-2-carbon­yl)-1-(pyridin-2-yl)cy­clo­hexa­nol, C35H27Br2N3O3, (III), all crystallize in different space groups, viz. Pbca, Fdd2 and Poverline{1}, respectively. In compound (II), the acetone molecule is disordered over two sets of atomic sites having occupancies of 0.690 (13) and 0.261 (13). Each of the cyclo­hexa­nol mol­ecules contains an intra­molecular O-H...N hydrogen bond and their overall mol­ecular conformations are fairly similar. The mol­ecules of (I) are linked by two independent C-H...O hydrogen bonds to form a C(5)C(10)[R22(15)] chain of rings, and those of (III) are linked by a combination of C-H...O and C-H...N hydrogen bonds, forming a chain of alternating R22(16) and R22(18) rings. The cyclo­hexa­nol mol­ecules in (II) are linked by a single C-H...N hydrogen bond to form simple C(4) chains and these chains are linked by a [pi]-[pi] stacking inter­action to form sheets, to which the disordered acetone molecules are weakly linked via a number of C-H...O contacts.