Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluorophenyl)-N-isopropyl-2-(methylsulfonyl)acetamide

Doreswamy Geetha, Haleyur G. Anil Kumar, Thaluru M. Mohan Kumar, Gejjalagere R. Srinivasa, Yeriyur B. Basavaraju, Hemmige S. Yathirajan, Sean Parkin

Research output: Contribution to journalArticlepeer-review


The synthesis and crystal structure of the title compound, C12H16FNO3S, which is related to the herbicide flufenacet, are presented. The dihedral angle between the amide group and the fluorinated benzene ring is 87.30 (5) and the N—C—C—S torsion angle defining the orientation of the methylsulfonyl substituent relative to the amide group is 106.91 (11). In the crystal, inversion-related molecules form dimers as a result of pairwise C—H․ ․ ․O hydrogen bonds, which appear to be reinforced by short O․ ․ ․π contacts [O․ ․ ․Cg = 3.0643 (11) Å]. A Hirshfeld surface analysis was used to quantify the various types of intermolecular contacts, which are dominated by H atoms.

Original languageEnglish
Pages (from-to)512-515
Number of pages4
JournalActa Crystallographica Section E: Crystallographic Communications
Issue numberPt 5
StatePublished - Apr 28 2023

Bibliographical note

Publisher Copyright:
© 2023 International Union of Crystallography. All rights reserved.


  • Hirshfeld surface analysis
  • N-(substituted phenyl)acetamide
  • crystal structure
  • flufenacet metabolite

ASJC Scopus subject areas

  • General Chemistry
  • General Materials Science
  • Condensed Matter Physics


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