Crystal structure and Hirshfeld analysis of 3'-bromo-4-methylchalcone and 3'-cyano-4- methylchalcone

Zachary O Battaglia, Jordan T Kersten, Elise M Nicol, Paloma Whitworth, Kraig A Wheeler, Charlie L Hall, Jason Potticary, Victoria Hamilton, Simon R Hall, Gemma D’Ambruoso, Masaomi Matsumoto, Stephen D Warren, Matthew E Cremens

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Two crystal structures of chalcones, or 1,3-diarylprop-2-en-1-ones, are
presented; both contain a methyl substitution on the 3-Ring, but differ on the
1-Ring, bromo versus cyano. The compounds are 30-bromo-4-methylchalcone
[systematic name: 1-(2-bromophenyl)-3-(4-methylphenyl)prop-2-en-1-one],
C16H13BrO, and 30-cyano-4-methylchalcone {systematic name: 2-[3-(4-methylphenyl)
prop-2-enoyl]benzonitrile}, C17H13NO. Both chalcones meaningfully
add to the large dataset of chalcone structures. The crystal structure of 30-cyano-
4-methylchalcone exhibits close contacts with the cyano nitrogen that do not
appear in previously reported disubstituted cyanochalcones, namely interactions
between the cyano nitrogen atom and a ring hydrogen atom as well as a methyl
hydrogen atom. The structure of 30-bromo-4-methylchalcone exhibits a type I
halogen bond, similar to that found in a previously reported structure for
Original languageEnglish
Pages (from-to)1496-1502
Number of pages7
JournalActa Crystallographica Section E: Crystallographic Communications
Publication statusAccepted/In press - 25 Aug 2020


  • crystal structure
  • chalcone
  • bromo
  • cyano
  • halogen bond
  • n-stacking
  • edge-to-face

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