Suppression of Disorder in Benzamide and Thiobenzamide Crystals by Fluorine Substitution

Alexander G. Shtukenberg, Doris E. Braun, Melissa Tan, Noalle Fellah, Bart Kahr

Research output: Contribution to journalArticlepeer-review


Disorder is a common feature of molecular crystals that complicates determination of structures and can potentially affect electric and mechanical properties. Suppression of disorder is observed in otherwise severely disordered benzamide and thiobenzamide crystals by substituting hydrogen with fluorine in the ortho-position of the phenyl ring. Fluorine occupancies of 20-30% are sufficient to suppress disorder without changing the packing motif. Crystal structure prediction calculations reveal a much denser lattice energy landscape for benzamide compared to 2-fluorobenzamide, suggesting that fluorine substitution makes disorder less likely.

Original languageEnglish (US)
Pages (from-to)5276-5284
Number of pages9
JournalCrystal Growth and Design
Issue number12
StatePublished - Jun 19 2024

ASJC Scopus subject areas

  • General Chemistry
  • General Materials Science
  • Condensed Matter Physics


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