A chalcone showing positional disorder, two related diarylcyclohexenones showing enantiomeric disorder and a related hydroxyterphenyl, all derived from simple carbonyl precursors

Vinutha V. Salian, Badiadka Narayana, Hemmige S. Yathirajan, Mehmet Akkurt, Omer Celik, Cem Cuneyt Ersanli, Christopher Glidewell*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Four compounds are reported, all of which lie along a versatile reaction pathway which leads from simple carbonyl compounds to terphenyls. (2E)-1-(2,4- Dichlorophenyl)-3-[4-(prop-1-en-2-yl)phenyl]prop-2-en-1-one, C18H14Cl2O, (I), prepared from 4-(prop-1-en-2-yl)benzaldehyde and 2,4-dichloroacetophenone, exhibits disorder over two sets of atomic sites having occupancies of 0.664 (6) and 0.336 (6). The related chalcone (2E)-3-(4-chlorophenyl)-1-(4-fluorophenyl)-prop-2-en-1-one reacts with acetone to produce (5RS)-3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]cyclohex-2-en-1-one, C21H21ClO, (II), which exhibits enantiomeric disorder with occupancies at the reference site of 0.662 (4) and 0.338 (4) for the (5R) and (5S) forms; the same chalcone reacts with methyl 3-oxobutanoate to give methyl (1RS, 6SR)-4-(4-chlorophenyl)-6-[4-(propan-2-yl)phenyl]-2-oxocyclohex-3-ene-1-carboxylate, C23H23ClO3, (III), where the reference site contains both (1R,6S) and (1S,6R) forms with occupancies of 0.923 (3) and 0.077 (3), respectively. Oxidation, using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, of ethyl (1RS, 6SR)-6-(4-bromophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate, prepared in a similar manner to (II) and (III), produces ethyl 4 ''-bromo-4-fluoro-5'-hydroxy-1,1':3',1 ''-terphenyl-4'-carboxylate, C21H16BrFO3, (IV), which crystallizes with Z' = 2 in the space group P (1) over bar. There are no significant intermolecular interactions in the structures of compounds (I) and (II), but for the major disorder component of compound (III), the molecules are linked into sheets by a combination of C-H center dot center dot center dot O and C-H center dot center dot center dot pi(arene) hydrogen bonds. The two independent molecules of compound (IV) form two different centrosymmetric dimers, one built from inversion-related pairs of C-H center dot center dot center dot O hydrogen bonds and the other from inversion-related pairs of C-H center dot center dot center dot pi(arene) hydrogen bonds. Comparisons are made with related compounds.

Original languageEnglish
Pages (from-to)610-617
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume71
Issue number7
Early online date26 Jun 2015
DOIs
Publication statusPublished - Jul 2015

Keywords

  • Chalcones
  • Diarylcyclohexenones
  • Terphenyls
  • Crystal structure
  • Supramolecular aggregation
  • Enantiomeric disorder
  • Hydrogen bonding
  • 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate

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