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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 [sigma](C-C) = 0.005 Å
R = 0.064
wR = 0.148
Data-to-parameter ratio = 13.9
Details
Open access

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

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[Tomizawa, M. & Casida, J. E. (2000). Toxicol. Appl. Pharmacol. 169, 114-120.]); Minamida et al. (1993[Minamida, I., Iwanaga, K. & Tabuchi, T. (1993). J. Pestic. Sci. 18, 31-40.]); Kashiwada et al. (1996[Kashiwada, Y. (1996). Agrochem. Jpn, 68, 18-19.]). For the synthesis, see: Zhang et al. (2010[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.]).

[Scheme 1]

Experimental

Crystal data
  • C23H26Cl2N4O4

  • Mr = 493.38

  • Triclinic, [P \overline 1]

  • a = 7.7948 (13) Å

  • b = 12.649 (2) Å

  • c = 13.021 (2) Å

  • [alpha] = 91.364 (3)°

  • [beta] = 98.765 (2)°

  • [gamma] = 107.878 (3)°

  • V = 1204.1 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.943, Tmax = 0.970

  • 7096 measured reflections

  • 4200 independent reflections

  • 3870 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.148

  • S = 1.17

  • 4200 reflections

  • 302 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tomizawa, M. & Casida, J. E. (2000). Toxicol. Appl. Pharmacol. 169, 114-120.  [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o3229  [ doi:10.1107/S1600536812043358 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.