(E)-3-(2-Chloro-3,3,3-trifluoro­prop-1-en­yl)-2,2-dimethyl-N,N-diphenyl­cyclo­propane­carboxamide

Fan-Yong Yan; Dong-Qing Liu

doi:10.1107/S1600536807060953

. 2007 Dec 6;64(Pt 1):o18. doi: 10.1107/S1600536807060953

(E)-3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N,N-diphenylcyclopropanecarboxamide

Fan-Yong Yan ^a,^*, Dong-Qing Liu ^a

PMCID: PMC2914980 PMID: 21200743

Abstract

The title compound, C₂₁H₁₉ClF₃NO, was synthesized from 3-[(E)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylic acid and diphenylamine. The propenyl and carboxamide substituents lie on the same side of the cyclopropane ring plane, with the two methyl substituents on either side of the plane. The phenyl rings of the carboxamide are inclined at an angle of 84.6 (3)° to one another. The F atoms are disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.

Related literature

For the preparation of the title compound, see: Liu et al. (2006 ▶). For the insecticidal properties of related compounds, see: Punja (1981 ▶).

Experimental

Crystal data

C₂₁H₁₉ClF₃NO
M _r = 393.82
Monoclinic,
a = 9.247 (6) Å
b = 21.443 (14) Å
c = 10.025 (7) Å
β = 99.068 (11)°
V = 1963 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 294 (2) K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.951, T _max = 0.960
11179 measured reflections
4030 independent reflections
2379 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.119
S = 1.00
4030 reflections
274 parameters
60 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807060953/sj2421sup1.cif

e-64-00o18-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060953/sj2421Isup2.hkl

e-64-00o18-Isup2.hkl^{(197.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the National Natural Science Foundation (No. 20376059)

supplementary crystallographic information

Comment

3-((E)-2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylic acid is a very important intermediate in the preparation of tefluthrinan a useful insecticide controlling a wide range of soil insect pests in maize, sugar beet, and other crops (Punja, 1981). Diphenylamine is also a structure which has bioactivity. We reasoned that a structure containing both of these bioactive components may show enhanced insecticidal activity and prepared the title compound (I), whose structure is repoerted here Fig. 1.

The the propenyl and carboxamide substituents lie on the same side of the cyclopropane ring plane, with the two methyl substituents on either side of the plane. The benzene rings of the carboxamide are inclined at 95.4 (3)° to one another. The crystal packing of (I) is shown in Fig. 2.

Experimental

The title compound was prepared according to the method of Liu et al. (2006). The product was recrystallized from methanol and ethyl acetate (5:1, v/v) over 3 days at ambient temperature, giving colourless single crystals of (I).