N-{(1Z)-1-[(6-Chloro­pyridin-3-ylmeth­yl)(eth­yl)amino]-3-(3-chloro­phen­yl)-2-nitro-5-oxohex-1-en­yl}-N-methyl­acetamide

Sun, C.-W.; Wu, Y.; Wang, J.

doi:10.1107/S1600536812043358

Volume 68
Part 11
Page o3229
November 2012

Received 21 September 2012
Accepted 18 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.064
wR = 0.148
Data-to-parameter ratio = 13.9
Details

N-{(1Z)-1-[(6-Chloropyridin-3-ylmethyl)(ethyl)amino]-3-(3-chlorophenyl)-2-nitro-5-oxohex-1-enyl}-N-methylacetamide

Chuan-Wen Sun,^a ^* Ying Wu ^a and Jing Wang ^a

^aDepartment of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai, 200234, People's Republic of China
Correspondence e-mail: xiaobuling123@126.com

In the title compound, C₂₃H₂₆Cl₂N₄O₄,the dihedral angle between the mean planes of the pyridine and 3-chlorophenyl rings is 22.63 (2)°. The nitro group is in a Z conformation.

Related literature

For general background to neonicotinoid compounds and their application as insecticides, see: Tomizawa & Casida, (2000); Minamida et al. (1993); Kashiwada et al. (1996). For the synthesis, see: Zhang et al. (2010).

Experimental

Crystal data

C₂₃H₂₆Cl₂N₄O₄
M_r = 493.38
Triclinic, $[P \overline 1]$
a = 7.7948 (13) Å
b = 12.649 (2) Å
c = 13.021 (2) Å
= 91.364 (3)°
= 98.765 (2)°
= 107.878 (3)°
V = 1204.1 (3) Å³
Z = 2
Mo K radiation
= 0.31 mm^-1
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.943, T_max = 0.970
7096 measured reflections
4200 independent reflections
3870 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.064
wR(F²) = 0.148
S = 1.17
4200 reflections
302 parameters
H-atom parameters constrained
_max = 0.47 e Å^-3
_min = -0.38 e Å^-3

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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: JJ2153 ).

Acknowledgements

The coauthors thank the National Natural Science Foundation of China (21042010, 21102092 and 30870560) for financial support.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kashiwada, Y. (1996). Agrochem. Jpn, 68, 18-19.
Minamida, I., Iwanaga, K. & Tabuchi, T. (1993). J. Pestic. Sci. 18, 31-40.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tomizawa, M. & Casida, J. E. (2000). Toxicol. Appl. Pharmacol. 169, 114-120.
Zhang, W. W., Yang, X. B., Chen, W. D., Xu, X. Y., Li, L., Zhai, H. B. & Li, Z. (2010). J. Agric. Food Chem. 58, 2741-2745.

organic compounds