Synthesis, spectroscopic and crystal structure studies of N-{3-cyano-1-[2,6-di-chloro-4-(tri-fluoro-meth-yl)phen-yl]-4-(ethyl-sulfan-yl)-1 H-pyrazol-5-yl}-2,2,2-tri-fluoro-acetamide

Prabhakar Priyanka; Bidarur K Jayanna; Yelekere C Sunil Kumar; Mellekatte T Shreenivas; Gejjelegere R Srinivasa; Thayamma R Divakara; Hemmige S Yathirajan; Sean Parkin

doi:10.1107/S2056989022009653

Synthesis, spectroscopic and crystal structure studies of N-{3-cyano-1-[2,6-di-chloro-4-(tri-fluoro-meth-yl)phen-yl]-4-(ethyl-sulfan-yl)-1 H-pyrazol-5-yl}-2,2,2-tri-fluoro-acetamide

Acta Crystallogr E Crystallogr Commun. 2022 Oct 4;78(Pt 11):1084-1088. doi: 10.1107/S2056989022009653. eCollection 2022 Nov 1.

Authors

Prabhakar Priyanka¹, Bidarur K Jayanna¹, Yelekere C Sunil Kumar², Mellekatte T Shreenivas², Gejjelegere R Srinivasa², Thayamma R Divakara³, Hemmige S Yathirajan⁴, Sean Parkin⁵

Affiliations

¹ Department of Chemistry, B.N.M. Institute of Technology, Bengaluru-560 070, India.
² Honeychem Pharma Research Pvt. Ltd., Peenya Industrial Area, Bengaluru-560 058, India.
³ T. John Institute of Technology, Bengaluru-560 083, India.
⁴ Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India.
⁵ Department of Chemistry, University of Kentucky, Lexington, KY, 40506-0055, USA.

Abstract

The structure of the title compound, C₁₅H₈N₄Cl₂F₆OS, a phenyl-pyrazole-based insecticide related to ethiprole, fipronil, and derivatives thereof is presented. The pyrazole ring has four chemically diverse substituents, namely a nitro-gen-bound 2,6-di-chloro-4-tri-fluoro-methyl-phenyl and carbon-bound cyano, ethyl-sulfanyl, and 2,2,2-tri-fluoro-acetamide groups. The pyrazole and phenyl rings are perpendicular, subtending a dihedral angle of 89.80 (5)°. In the crystal, strong N-H⋯O hydrogen bonds link the mol-ecules into chains that extend parallel to the a-axis.

Keywords: crystal structure; insecticide; phenylpyrazole.

Grants and funding

HSY is grateful to UGC, New Delhi, for the award of BSR Faculty Fellowship for three years. Funding for this research was provided by: NSF (MRI CHE1625732) and the University of Kentucky (Bruker D8 Venture diffractometer).