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*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

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(4fluoropheny1)-2,4-bis(pyridine-2-carbony1)-1 -(pyridin-2-yl)cyclohexanol, C35H27F2N3O3, (I), (1RS,2SR,3SR,4RS,5RS)-3,5bis(4-chloropheny1)-2,4-bis(pyridine-2-carbony1)-1 -(pyridin-2yl)cyclohexanol acetone 0.951-solvate, C35H27Cl2N3O3 center dot 0.951C(3)H(6)O, (II), and (1RS,2SR,3SR,4RS,5RS)-3,5-bis(4bromopheny1)-2,4-bis(pyridine-2-carbony1)-1-(pyridin-2-y1)cy- clohexanol, C35H27Br2N3O3, (III), all crystallize in different space groups, viz. Pbca, Fdd2 and Pit, 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 center dot center dot center dot N hydrogen bond and their overall molecular conformations are fairly similar. The molecules of (I) are linked by two independent C-H center dot center dot center dot O hydrogen bonds to form a C(5)C(10)[R-2(2)(15)] chain of rings, and those of (III) are linked by a combination of C-H center dot center dot center dot O and C-H center dot center dot center dot N hydrogen bonds, forming a chain of alternating Ri(16) and R-2(2)(18) rings. The cyclohexanol molecules in (II) are linked by a single C-H center dot center dot center dot 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 center dot center dot center dot O contacts.

Original languageEnglish
Pages (from-to)953-U158
Number of pages29
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume70
DOIs
Publication statusPublished - Oct 2014

Keywords

  • crystal structure
  • highly substituted cyclohexanols
  • supramolecular assembly
  • hydrogen bonding
  • Michael addition
  • condensation reactions
  • CARBON
  • RADII

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