Synthesis and X-ray crystal structure of a new potent pyrethroid acid, (±)-cis-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylic acid

Abstract

Single-crystal X-ray analysis of the title compound has established its structure and molecular geometry. Crystals are monoclinic, space group P2₁/c, with a= 9.487(4), b= 8.009(4), c= 16.214(6)Å, β= 119.91(1)°, Z= 4. The structure was solved by direct methods and refined by full-matrix least-squares calculations to R 0.056 over 1 242 reflections measured by diffractometer. The crystals contain centrosymmetric hydrogen-bonded dimers (O ⋯ O 2.65 Å) in which the carboxy and vinyl substituents are in a ‘bisecting’ orientation, and the CO group and one of hydrogen atoms on each methyl group point over the cyclopropane ring. The bond lengths in the ring reflect the substitution pattern.