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Volume 65 
Part 10 
Page o2517  
October 2009  

Received 26 July 2009
Accepted 17 September 2009
Online 26 September 2009

[bx2230sup1]
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Key indicators
Single-crystal X-ray study
T = 290 K
Mean [sigma](C-C) = 0.004 Å
R = 0.049
wR = 0.135
Data-to-parameter ratio = 16.6
Details
Open access

1-[(6-Chloro-3-pyridyl)methyl]-5-ethoxy-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine

Zhongzhen Tian,a* Dongmei Lia and Zhong Lib*

aInstitute of Chemistry and Chemical Engineering, University of Jinan, 106 Jiwei Road, Jinan 250022, People's Republic of China, and bShanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, People's Republic of China
Correspondence e-mail: chm_tianzz@ujn.edu.cn, lizhong@ecust.edu.cn

In the title compound, C15H19ClN4O3, an active agrochemical possessing insecticidal activity, the dihedral angle between the mean planes passing through the pyridine ring and the five-membered ring is 87.3 (2)°. The fused pyridine ring adopts a twisted sofa conformation. The molecular structure features close intramolecular C-H...N and C-H...O hydrogen bonding.

Related literature

For related literature, see: Kagabu et al. (2002[Kagabu, S., Nishiwaki, H., Sato, K., Hibi, M., Yamaoka, N. & Nakagawa, Y. (2002). Pest. Manag. Sci. 58, 483-490.]); Moriya et al. (1992[Moriya, K., Shibuya, K., Hattori, Y., Tsuboi, S., Shiokawa, K. & Kagabu, S. (1992). Biosci. Biotechnol. Biochem. 56, 364-365.]); Tian et al. (2007[Tian, Z. Z., Shao, X. S., Li, Z., Qian, X. H. & Huang, Q. C. (2007). J. Agric. Food. Chem. 55, 2288-2292.]); Tokumitsu (1990[Tokumitsu, T. (1990). Bull. Chem. Soc. Jpn, 63, 1921-1924.]).

[Scheme 1]

Experimental

Crystal data

  • C15H19ClN4O3

  • Mr = 338.79

  • Monoclinic, P 21 /c

  • a = 17.021 (3) Å

  • b = 5.5737 (8) Å

  • c = 18.334 (3) Å

  • [beta] = 112.097 (3)°

  • V = 1611.6 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 290 K

  • 0.50 × 0.24 × 0.12 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.922, Tmax = 0.969

  • 8970 measured reflections

  • 3486 independent reflections

  • 1870 reflections with I > 2[sigma](I)

  • Rint = 0.082
Refinement

  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.135

  • S = 0.82

  • 3486 reflections

  • 210 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11B...O3 0.97 2.35 2.803 (3) 108
C13-H13...N1 0.93 2.54 2.891 (3) 103

Data collection: SMART (Bruker, 1997[Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SADABS, 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2230 ).

Acknowledgements

The authors thank the Opening Fund of Shanghai Key Laboratory of Chemical Biology (grant No. SKLCB-2008-08) and the Doctoral Foundation of the University of Jinan (grant No. XBS0823, B0542) for financial support.

References

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Kagabu, S., Nishiwaki, H., Sato, K., Hibi, M., Yamaoka, N. & Nakagawa, Y. (2002). Pest. Manag. Sci. 58, 483-490.  [CrossRef] [PubMed] [ChemPort]
Moriya, K., Shibuya, K., Hattori, Y., Tsuboi, S., Shiokawa, K. & Kagabu, S. (1992). Biosci. Biotechnol. Biochem. 56, 364-365.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tian, Z. Z., Shao, X. S., Li, Z., Qian, X. H. & Huang, Q. C. (2007). J. Agric. Food. Chem. 55, 2288-2292.  [CrossRef] [PubMed] [ChemPort]
Tokumitsu, T. (1990). Bull. Chem. Soc. Jpn, 63, 1921-1924.  [CrossRef] [ChemPort]

Acta Cryst (2009). E65, o2517  [ doi:10.1107/S1600536809037660 ]

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