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

Seranthimata Samshuddin; Jerry P Jasinski; Ray J Butcher; Elizabeth A Neuhardt; Badiadka Narayana; Hemmige S Yathirajan; Christopher Glidewell

doi:10.1107/S2053229614019937

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

Acta Crystallogr C Struct Chem. 2014 Oct;70(Pt 10):953-9. doi: 10.1107/S2053229614019937. Epub 2014 Sep 28.

Authors

Seranthimata Samshuddin¹, Jerry P Jasinski², Ray J Butcher³, Elizabeth A Neuhardt², Badiadka Narayana¹, Hemmige S Yathirajan⁴, Christopher Glidewell⁵

Affiliations

¹ Department of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India.
² Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA.
³ Department of Chemistry, Howard University, 525 College Street, Washington NW, DC 20059, USA.
⁴ Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India.
⁵ School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.

PMID: 25279595
DOI: 10.1107/S2053229614019937

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 and P1, 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)[R2(2)(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 R2(2)(16) and R2(2)(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 π-π stacking interaction to form sheets, to which the disordered acetone molecules are weakly linked via a number of C-H···O contacts.

Keywords: Michael addition; condensation reactions; crystal structure; highly substituted cyclohexanols; hydrogen bonding; supramolecular assembly.