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

doi:10.1107/S2056989023003675

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

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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 language	English
Pages (from-to)	512-515
Number of pages	4
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	79
Issue number	Pt 5
DOIs	https://doi.org/10.1107/S2056989023003675
State	Published - Apr 28 2023

Bibliographical note

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

Funding

DG is grateful to the DOS in Chemistry, University of Mysore for providing research facilities. HSY thanks UGC for a BSR Faculty fellowship for three years.

Funders
U.S. Department of State
University Grants Commission

Keywords

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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10.1107/S2056989023003675

Cite this

Geetha, D., Anil Kumar, H. G., Mohan Kumar, T. M., Srinivasa, G. R., Basavaraju, Y. B., Yathirajan, H. S., & Parkin, S. (2023). Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluorophenyl)-N-isopropyl-2-(methylsulfonyl)acetamide. Acta Crystallographica Section E: Crystallographic Communications, 79(Pt 5), 512-515. https://doi.org/10.1107/S2056989023003675

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

abstract = "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) {\AA}]. A Hirshfeld surface analysis was used to quantify the various types of intermolecular contacts, which are dominated by H atoms.",

keywords = "Hirshfeld surface analysis, N-(substituted phenyl)acetamide, crystal structure, flufenacet metabolite",

author = "Doreswamy Geetha and \{Anil Kumar\}, \{Haleyur G.\} and \{Mohan Kumar\}, \{Thaluru M.\} and Srinivasa, \{Gejjalagere R.\} and Basavaraju, \{Yeriyur B.\} and Yathirajan, \{Hemmige S.\} and Sean Parkin",

year = "2023",

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doi = "10.1107/S2056989023003675",

language = "English",

volume = "79",

pages = "512--515",

number = "Pt 5",

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Geetha, D, Anil Kumar, HG, Mohan Kumar, TM, Srinivasa, GR, Basavaraju, YB, Yathirajan, HS & Parkin, S 2023, 'Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluorophenyl)-N-isopropyl-2-(methylsulfonyl)acetamide', Acta Crystallographica Section E: Crystallographic Communications, vol. 79, no. Pt 5, pp. 512-515. https://doi.org/10.1107/S2056989023003675

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. et al.
In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 79, No. Pt 5, 28.04.2023, p. 512-515.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluorophenyl)-N-isopropyl-2-(methylsulfonyl)acetamide

AU - Geetha, Doreswamy

AU - Anil Kumar, Haleyur G.

AU - Mohan Kumar, Thaluru M.

AU - Srinivasa, Gejjalagere R.

AU - Basavaraju, Yeriyur B.

AU - Yathirajan, Hemmige S.

AU - Parkin, Sean

PY - 2023/4/28

Y1 - 2023/4/28

N2 - 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.

AB - 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.

KW - Hirshfeld surface analysis

KW - N-(substituted phenyl)acetamide

KW - crystal structure

KW - flufenacet metabolite

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U2 - 10.1107/S2056989023003675

DO - 10.1107/S2056989023003675

M3 - Article

AN - SCOPUS:85159572544

SN - 2056-9890

VL - 79

SP - 512

EP - 515

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

IS - Pt 5

ER -

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

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

Access to Document

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