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

Abstract

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 andP\overline{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 aC(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 alternatingR22(16) andR22(18) rings. The cyclohexanol molecules in (II) are linked by a single C—H...N hydrogen bond to form simpleC(4) chains and these chains are linked by a π–π stacking interaction to form sheets, to which the disordered acetone molecules are weakly linkedviaa number of C—H...O contacts.