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

Kant, R.; Gupta, V.K.; Kapoor, K.; Deshmukh, M.B.; Shripanavar, C.S.

doi:10.1107/S1600536811053487

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 (C-C) = 0.003 Å
R = 0.041
wR = 0.108
Data-to-parameter ratio = 18.0
Details

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

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a Madhukar B. Deshmukh ^b and Chetan S. Shripanavar ^b

^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-HCl and C-HCl 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); Schulz-Jander et al. (2002); Dai et al. (2010); Tanner (2010). For ring conformations, see: Duax & Norton (1975). For related structures, see: Kapoor et al. (2011).

Experimental

Crystal data

C₉H₁₂ClN₄⁺·Cl^-
M_r = 247.13
Triclinic, $[P \overline 1]$
a = 6.4773 (3) Å
b = 7.3091 (3) Å
c = 12.4758 (4) Å
= 88.996 (3)°
= 77.214 (3)°
= 79.925 (3)°
V = 566.98 (4) Å³
Z = 2
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.742, T_max = 1.000
14139 measured reflections
2468 independent reflections
2059 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.108
S = 1.03
2468 reflections
137 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N13-H13ACl2	0.86	2.39	3.227 (2)	166
N13-H13BCl2ⁱ	0.86	2.33	3.177 (2)	169
N11-H11Cl2ⁱⁱ	0.86	2.60	3.182 (2)	126
C7-H7ACl2ⁱⁱⁱ	0.97	2.69	3.650 (2)	169
C7-H7BCl2	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).

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.
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.
Kanne, D. B., Dick, R. A., Tomizawa, M. & Casida, J. E. (2005). Chem. Res. Toxicol. 18, 1479-1484.
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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tanner, G. (2010). MSc thesis, Austrian Agency for Health and Food Safety, Vienna.

organic compounds