[Journal logo]

Volume 68 
Part 1 
Page o147  
January 2012  

Received 8 December 2011
Accepted 12 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.108
Data-to-parameter ratio = 18.0
Details
Open access

1-[(6-Chloropyridin-3-yl)methyl]imidazolidin-2-iminium chloride

aX-ray Crystallography Laboratory, Post-Graduate Department of Physics, University of Jammu, Jammu Tawi 180 006, India, and bDepartment of Chemistry, Shivaji University, Kolhapur 416 004, India
Correspondence e-mail: rkvk.paper11@gmail.com

The title compound, C9H12ClN4+·Cl-, is a natural metabolic product of imidacloprid [systematic name: (E)-1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine] and was obtained by the reduction of the latter using Fe in HCl. The dihedral angle between the pyridine and imidazole rings is 62.09 (12)°. The crystal structure is stabilized by N-H...Cl and C-H...Cl interactions involving the chloride anion. The pyridine N and the chloride atoms are not involved in intermolecular interactions.

Related literature

For background to the insecticidal applications of imidacloprid, see: Kanne et al. (2005[Kanne, D. B., Dick, R. A., Tomizawa, M. & Casida, J. E. (2005). Chem. Res. Toxicol. 18, 1479-1484.]); Schulz-Jander et al. (2002[Schulz-Jander, D. A., Leimkuehler, W. M. & Casida, J. E. (2002). Chem. Res. Toxicol. 15, 1158-1165.]); Dai et al. (2010[Dai, Y., Ji, W., Chen, T., Zhang, W., Liu, Z., Ge, F. & Yuan, S. (2010). J. Agric. Food Chem. 58, 2419-2425.]); Tanner (2010[Tanner, G. (2010). MSc thesis, Austrian Agency for Health and Food Safety, Vienna.]). For ring conformations, see: Duax & Norton (1975[Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.]). For related structures, see: Kapoor et al. (2011[Kapoor, K., Gupta, V. K., Kant, R., Deshmukh, M. B. & Sripanavar, C. S. (2011). X-ray Struct. Anal. Online, 27, x55-x56.]).

[Scheme 1]

Experimental

Crystal data
  • C9H12ClN4+·Cl-

  • Mr = 247.13

  • Triclinic, [P \overline 1]

  • a = 6.4773 (3) Å

  • b = 7.3091 (3) Å

  • c = 12.4758 (4) Å

  • [alpha] = 88.996 (3)°

  • [beta] = 77.214 (3)°

  • [gamma] = 79.925 (3)°

  • V = 566.98 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.55 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.1 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.742, Tmax = 1.000

  • 14139 measured reflections

  • 2468 independent reflections

  • 2059 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.108

  • S = 1.03

  • 2468 reflections

  • 137 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N13-H13A...Cl2 0.86 2.39 3.227 (2) 166
N13-H13B...Cl2i 0.86 2.33 3.177 (2) 169
N11-H11...Cl2ii 0.86 2.60 3.182 (2) 126
C7-H7A...Cl2iii 0.97 2.69 3.650 (2) 169
C7-H7B...Cl2 0.97 2.80 3.722 (2) 158
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x, y-1, z; (iii) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2070 ).


Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. He also thanks the UGC for research funding under research project F. No. 37-415/2009 (J&K) (SR).

References

Dai, Y., Ji, W., Chen, T., Zhang, W., Liu, Z., Ge, F. & Yuan, S. (2010). J. Agric. Food Chem. 58, 2419-2425.  [ISI] [CrossRef] [ChemPort] [PubMed]
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Kanne, D. B., Dick, R. A., Tomizawa, M. & Casida, J. E. (2005). Chem. Res. Toxicol. 18, 1479-1484.  [CrossRef] [PubMed] [ChemPort]
Kapoor, K., Gupta, V. K., Kant, R., Deshmukh, M. B. & Sripanavar, C. S. (2011). X-ray Struct. Anal. Online, 27, x55-x56.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Schulz-Jander, D. A., Leimkuehler, W. M. & Casida, J. E. (2002). Chem. Res. Toxicol. 15, 1158-1165.  [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tanner, G. (2010). MSc thesis, Austrian Agency for Health and Food Safety, Vienna.


Acta Cryst (2012). E68, o147  [ doi:10.1107/S1600536811053487 ]

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.