Crystal structure of the insecticide ethiprole (C13H9Cl2F3N4OS): A case study of whole-molecule configurational disorder

Vinaya; Yeriyur B. Basavaraju; Gejjelegere R. Srinivasa; Mellekatte T. Shreenivas; Hemmige S. Yathirajan; Sean Parkin

doi:10.1107/S205698902300035X

Crystal structure of the insecticide ethiprole (C₁₃H₉Cl₂F₃N₄OS): A case study of whole-molecule configurational disorder

Vinaya, Yeriyur B. Basavaraju, Gejjelegere R. Srinivasa, Mellekatte T. Shreenivas, Hemmige S. Yathirajan, Sean Parkin

Chemistry

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

4 Scopus citations

Abstract

The crystal structure of ethiprole {systematic name: 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethanesulfinyl-1H-imidazole-3-carbonitrile}, C13H9Cl2F3N4OS, a phenylpyrazole-based insecticide, is presented. The pyrazole ring carries four substituents: An N-bound 2,6-dichloro-4-Trifluoromethylphenyl ring and C-bound amine, ethanesulfinyl, and cyano groups. The sulfur atom of the ethanesulfinyl group is trigonal-pyramidal and stereogenic. The structure exhibits whole-molecule configurational disorder due to superposition of enantiomers. The crystal packing is dominated by strong N-H O and N-H N hydrogen bonds, which form R 44 (18) and R 22 (12) ring motifs. Since the ethiprole molecule is quite small, and structure solution and refinement were straightforward, the structure presents a convenient instructional example for modelling whole-body disorder of a non-rigid molecule. To this end, a step-by-step overview of the model-building and refinement process is also given. The structure could form the basis of a useful classroom, practical, or workshop-style example.

Original language	English
Pages (from-to)	54-59
Number of pages	6
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	79
DOIs	https://doi.org/10.1107/S205698902300035X
State	Published - Jan 19 2023

Bibliographical note

Funding Information:
Funding for this research was provided by: NSF (MRI CHE1625732) and the University of Kentucky (Bruker D8 Venture diffractometer) to SP.

Funding Information:
One of the authors (V) is grateful to the DST–PURSE Project, Vijnana Bhavana, UOM for providing research facilities. HSY thanks UGC for a BSR Faculty fellowship for three years.

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

Keywords

configurational disorder
crystal structure
ethiprole
instructional tool
phenylpyrazole insecticide
refinement strategy
whole-molecule disorder

ASJC Scopus subject areas

Chemistry (all)
Materials Science (all)
Condensed Matter Physics

Access to Document

10.1107/S205698902300035X

Cite this

@article{f631b3076b5543bd9f7235e985c482fc,

title = "Crystal structure of the insecticide ethiprole (C13H9Cl2F3N4OS): A case study of whole-molecule configurational disorder",

abstract = "The crystal structure of ethiprole {systematic name: 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethanesulfinyl-1H-imidazole-3-carbonitrile}, C13H9Cl2F3N4OS, a phenylpyrazole-based insecticide, is presented. The pyrazole ring carries four substituents: An N-bound 2,6-dichloro-4-Trifluoromethylphenyl ring and C-bound amine, ethanesulfinyl, and cyano groups. The sulfur atom of the ethanesulfinyl group is trigonal-pyramidal and stereogenic. The structure exhibits whole-molecule configurational disorder due to superposition of enantiomers. The crystal packing is dominated by strong N-H O and N-H N hydrogen bonds, which form R 44 (18) and R 22 (12) ring motifs. Since the ethiprole molecule is quite small, and structure solution and refinement were straightforward, the structure presents a convenient instructional example for modelling whole-body disorder of a non-rigid molecule. To this end, a step-by-step overview of the model-building and refinement process is also given. The structure could form the basis of a useful classroom, practical, or workshop-style example.",

keywords = "configurational disorder, crystal structure, ethiprole, instructional tool, phenylpyrazole insecticide, refinement strategy, whole-molecule disorder",

author = "Vinaya and Basavaraju, {Yeriyur B.} and Srinivasa, {Gejjelegere R.} and Shreenivas, {Mellekatte T.} and Yathirajan, {Hemmige S.} and Sean Parkin",

note = "Funding Information: Funding for this research was provided by: NSF (MRI CHE1625732) and the University of Kentucky (Bruker D8 Venture diffractometer) to SP. Funding Information: One of the authors (V) is grateful to the DST–PURSE Project, Vijnana Bhavana, UOM for providing research facilities. HSY thanks UGC for a BSR Faculty fellowship for three years. Publisher Copyright: {\textcopyright} 2023 International Union of Crystallography. All rights reserved.",

year = "2023",

month = jan,

day = "19",

doi = "10.1107/S205698902300035X",

language = "English",

volume = "79",

pages = "54--59",

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T1 - Crystal structure of the insecticide ethiprole (C13H9Cl2F3N4OS)

T2 - A case study of whole-molecule configurational disorder

AU - Vinaya,

AU - Basavaraju, Yeriyur B.

AU - Srinivasa, Gejjelegere R.

AU - Shreenivas, Mellekatte T.

AU - Yathirajan, Hemmige S.

AU - Parkin, Sean

N1 - Funding Information: Funding for this research was provided by: NSF (MRI CHE1625732) and the University of Kentucky (Bruker D8 Venture diffractometer) to SP. Funding Information: One of the authors (V) is grateful to the DST–PURSE Project, Vijnana Bhavana, UOM for providing research facilities. HSY thanks UGC for a BSR Faculty fellowship for three years. Publisher Copyright: © 2023 International Union of Crystallography. All rights reserved.

PY - 2023/1/19

Y1 - 2023/1/19

N2 - The crystal structure of ethiprole {systematic name: 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethanesulfinyl-1H-imidazole-3-carbonitrile}, C13H9Cl2F3N4OS, a phenylpyrazole-based insecticide, is presented. The pyrazole ring carries four substituents: An N-bound 2,6-dichloro-4-Trifluoromethylphenyl ring and C-bound amine, ethanesulfinyl, and cyano groups. The sulfur atom of the ethanesulfinyl group is trigonal-pyramidal and stereogenic. The structure exhibits whole-molecule configurational disorder due to superposition of enantiomers. The crystal packing is dominated by strong N-H O and N-H N hydrogen bonds, which form R 44 (18) and R 22 (12) ring motifs. Since the ethiprole molecule is quite small, and structure solution and refinement were straightforward, the structure presents a convenient instructional example for modelling whole-body disorder of a non-rigid molecule. To this end, a step-by-step overview of the model-building and refinement process is also given. The structure could form the basis of a useful classroom, practical, or workshop-style example.

AB - The crystal structure of ethiprole {systematic name: 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethanesulfinyl-1H-imidazole-3-carbonitrile}, C13H9Cl2F3N4OS, a phenylpyrazole-based insecticide, is presented. The pyrazole ring carries four substituents: An N-bound 2,6-dichloro-4-Trifluoromethylphenyl ring and C-bound amine, ethanesulfinyl, and cyano groups. The sulfur atom of the ethanesulfinyl group is trigonal-pyramidal and stereogenic. The structure exhibits whole-molecule configurational disorder due to superposition of enantiomers. The crystal packing is dominated by strong N-H O and N-H N hydrogen bonds, which form R 44 (18) and R 22 (12) ring motifs. Since the ethiprole molecule is quite small, and structure solution and refinement were straightforward, the structure presents a convenient instructional example for modelling whole-body disorder of a non-rigid molecule. To this end, a step-by-step overview of the model-building and refinement process is also given. The structure could form the basis of a useful classroom, practical, or workshop-style example.

KW - configurational disorder

KW - crystal structure

KW - ethiprole

KW - instructional tool

KW - phenylpyrazole insecticide

KW - refinement strategy

KW - whole-molecule disorder

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