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...
Autores principales: | , , , , , , |
---|---|
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 |