Cargando…

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

The synthesis and crystal structure of the title compound, C(12)H(16)FNO(3)S, 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 methyl­su...

Descripción completa

Detalles Bibliográficos
Autores principales: Geetha, Doreswamy, Anil Kumar, Haleyur G., Mohan Kumar, Thaluru M., Srinivasa, Gejjalagere R., Basavaraju, Yeriyur B., Yathirajan, Hemmige S., Parkin, Sean
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10162089/
https://www.ncbi.nlm.nih.gov/pubmed/37151839
http://dx.doi.org/10.1107/S2056989023003675
_version_ 1785037627688222720
author Geetha, Doreswamy
Anil Kumar, Haleyur G.
Mohan Kumar, Thaluru M.
Srinivasa, Gejjalagere R.
Basavaraju, Yeriyur B.
Yathirajan, Hemmige S.
Parkin, Sean
author_facet Geetha, Doreswamy
Anil Kumar, Haleyur G.
Mohan Kumar, Thaluru M.
Srinivasa, Gejjalagere R.
Basavaraju, Yeriyur B.
Yathirajan, Hemmige S.
Parkin, Sean
author_sort Geetha, Doreswamy
collection PubMed
description The synthesis and crystal structure of the title compound, C(12)H(16)FNO(3)S, 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.
format Online
Article
Text
id pubmed-10162089
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-101620892023-05-06 Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluoro­phen­yl)-N-isopropyl-2-(methyl­sulfon­yl)acetamide Geetha, Doreswamy Anil Kumar, Haleyur G. Mohan Kumar, Thaluru M. Srinivasa, Gejjalagere R. Basavaraju, Yeriyur B. Yathirajan, Hemmige S. Parkin, Sean Acta Crystallogr E Crystallogr Commun Research Communications The synthesis and crystal structure of the title compound, C(12)H(16)FNO(3)S, 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. International Union of Crystallography 2023-04-28 /pmc/articles/PMC10162089/ /pubmed/37151839 http://dx.doi.org/10.1107/S2056989023003675 Text en © Geetha et al. 2023 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Geetha, Doreswamy
Anil Kumar, Haleyur G.
Mohan Kumar, Thaluru M.
Srinivasa, Gejjalagere R.
Basavaraju, Yeriyur B.
Yathirajan, Hemmige S.
Parkin, Sean
Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluoro­phen­yl)-N-isopropyl-2-(methyl­sulfon­yl)acetamide
title Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluoro­phen­yl)-N-isopropyl-2-(methyl­sulfon­yl)acetamide
title_full Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluoro­phen­yl)-N-isopropyl-2-(methyl­sulfon­yl)acetamide
title_fullStr Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluoro­phen­yl)-N-isopropyl-2-(methyl­sulfon­yl)acetamide
title_full_unstemmed Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluoro­phen­yl)-N-isopropyl-2-(methyl­sulfon­yl)acetamide
title_short Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluoro­phen­yl)-N-isopropyl-2-(methyl­sulfon­yl)acetamide
title_sort synthesis, crystal structure and hirshfeld surface analysis of n-(4-fluoro­phen­yl)-n-isopropyl-2-(methyl­sulfon­yl)acetamide
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10162089/
https://www.ncbi.nlm.nih.gov/pubmed/37151839
http://dx.doi.org/10.1107/S2056989023003675
work_keys_str_mv AT geethadoreswamy synthesiscrystalstructureandhirshfeldsurfaceanalysisofn4fluorophenylnisopropyl2methylsulfonylacetamide
AT anilkumarhaleyurg synthesiscrystalstructureandhirshfeldsurfaceanalysisofn4fluorophenylnisopropyl2methylsulfonylacetamide
AT mohankumarthalurum synthesiscrystalstructureandhirshfeldsurfaceanalysisofn4fluorophenylnisopropyl2methylsulfonylacetamide
AT srinivasagejjalagerer synthesiscrystalstructureandhirshfeldsurfaceanalysisofn4fluorophenylnisopropyl2methylsulfonylacetamide
AT basavarajuyeriyurb synthesiscrystalstructureandhirshfeldsurfaceanalysisofn4fluorophenylnisopropyl2methylsulfonylacetamide
AT yathirajanhemmiges synthesiscrystalstructureandhirshfeldsurfaceanalysisofn4fluorophenylnisopropyl2methylsulfonylacetamide
AT parkinsean synthesiscrystalstructureandhirshfeldsurfaceanalysisofn4fluorophenylnisopropyl2methylsulfonylacetamide