3-[(E)-2-Chloro-3,3,3-trifluoro­prop-1-en-1-yl]-N-(2-fluoro­phen­yl)-2,2-dimethyl­cyclo­propane-1-carboxamide

Yan, F.-Y.; Liu, D.-Q.; Wen, J.-Y.; Gao, Y.-Y.; Li, A.-M.

doi:10.1107/S1600536810050464

Volume 67
Part 1
Page o60
January 2011

Received 16 November 2010
Accepted 2 December 2010
Online 11 December 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.135
Data-to-parameter ratio = 16.9
Details

3-[(E)-2-Chloro-3,3,3-trifluoroprop-1-en-1-yl]-N-(2-fluorophenyl)-2,2-dimethylcyclopropane-1-carboxamide

Fan-Yong Yan,^a ^* Dong-Qing Liu,^b Jing-Yun Wen,^c Yun-Ying Gao ^c and Ai-Mei Li ^c

^aKey Laboratoy of Hollow Fiber Membrane Materials & Membrane Processes, School of Environmental & Chemical Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China,^bSchool of Materials Science and Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China, and ^cSchool of Environmental & Chemical Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China
Correspondence e-mail: yfytju@yahoo.com

The phenyl ring in the title compound, C₁₅H₁₄ClF₄NO, makes a dihedral angle of 80.3 (3)° with the cyclopropane ring. In the crystal, molecules are linked by N-HO hydrogen bonds into chains running along the a axis.

Related literature

The title compound is an intermediate for tefluthrin, an insecticide controlling a wide range of soil insect pests, see: Punja (1981). For the synthesis of the title compound, see: Liu & Yan (2007).

Experimental

Crystal data

C₁₅H₁₄ClF₄NO
M_r = 335.72
Orthorhombic, P b c a
a = 9.4604 (19) Å
b = 17.785 (4) Å
c = 18.879 (4) Å
V = 3176.6 (11) Å³
Z = 8
Mo K radiation
= 0.28 mm^-1
T = 293 K
0.40 × 0.06 × 0.06 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.896, T_max = 0.983
28794 measured reflections
3488 independent reflections
2848 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.135
S = 1.07
3488 reflections
206 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.29 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.84 (2)	2.13 (2)	2.9549 (18)	167.3 (18)
Symmetry code: (i) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5406 ).

Acknowledgements

This work was supported by the National Natural Science Foundation (No. 20376059) and Tianjin Polytechnic University

References

Liu, D.-Q. & Yan, F.-Y. (2007). Acta Cryst. E63, o4202.
Punja, N. (1981). Eur. Patent EP 0031199.
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds