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

Samshuddin, S. and Jasinski, J. P. and Butcher, Ray J. and Neuhardt, E. A. and Narayana, B. and Yathirajan, H. S. and Glidewell, Christopher (2014) Three closely-related cyclohexanols (C35H27X2N3O3; X = F, Cl or Br): Similar molecular structures but different crystal structures. Acta Crystallographica Section C: Structural Chemistry, 70. pp. 953-959. ISSN 2053-2296

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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 P\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 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.

Item Type: Article
Uncontrolled Keywords: Crystal structure, Hydrogen bonds, Molecules, Condensation reactions, Chains, Molecular conformation, Supramolecular assemblies, Complexation, Addition reactions, Acetone, 2-acetylpyridine, Acetone molecules, Financial markets, highly substituted cyclohexanols, Michael additions, O rings, Pyridine, Space Groups, Stacking interaction
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Arshiya Kousar Library Assistant
Date Deposited: 03 Sep 2019 05:27
Last Modified: 21 Jul 2022 10:19

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