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

In the title molecule, C9H10ClN3O, the dihedral angle between the pyridine ring and imidazoline ring mean plane [maximum deviation = 0.031–(3) Å] is 76.2 (1)°. In the crystal, N—H⋯O hydrogen bonds link pairs of molecules to form inversion dimers. In addition, weak C—H⋯N hydrogen bonds and π–π stacking interactions between pyridine rings [centroid–centroid distance = 3.977 (2) Å] are observed.


Crystal data
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 Imidacloprid is an insecticide which acts as an agonist of the acetylcholine receptor of insect nervous system. Oral, acute and chronic toxicity of imidacloprid and its main metabolite 1-[(6-chloropyridin-3-yl)methyl] imidazolidin-2-one (urea derivative) in mid-gut and rectum were investigated in Apis mellifera (Suchail et al., 2001;Suchail et al., 2004). Acute intoxication by imidacloprid or its metabolites results in rapid appearance of neurotoxicity symptoms, such as hyperresponsiveness and, hyperactivity (Suchail et al., 2001). Many metabolites of imidacloprid have been identified, but the enzymatic basis for their formation has not been reported in many cases (Schulz-Jander & Casida, 2002). Imidacloprid is degraded by liver enzymes to other nitroimines such as the corresponding guanidine and urea derivatives. The fate of imidacloprid in soil environment in terms of the metabolites toxic to vertebrates has been reported by Pandey et al. (2009). The supreme biological profile of imidacloprid is giving impulse to the development of new products by modifying the structural features of the prototype (Kagabu et al., 2007). Therefore, in a search for new neonicotinoid insecticides with improved profiles, some neonicotinoid derivatives have been designed and synthesized. The crystal structure of the title compound (I) is shown in Fig. 1.
The bond lengths and angles in (I) show normal values and are comparable with related structures (Kapoor et al., 2011Kant et al., 2012). The plane through the pyridine ring forms dihedral angle of 76.2 (1)Å with the imidazoline ring plane. In the crystal, N-H···O hydrogen bonds link pairs of molecules to form inversion dimers (Fig. 2). These dimers are linked by weak C-H···N interactions. The crystal structure is further stabilized by π-π interactions between the pyridine ring of the molecule at (x, y, z) and the pyridine ring of an inversion related molecule at (1 -x, -y, -z) [centroid separation = 3.977 (2) Å, interplanar spacing = 3.267 Å and centroid shift = 2.267 Å].
Experimental Imidacloprid (0.256 g, 0.001 mol) was dissolved in 5 ml methanol and to it 5 ml of 1 N NaOH solution was added. The reaction mixture was refluxed for about 10 hrs on a water bath at 343K and then cooled. The reaction mixture was neutralized with 1 N HCl solution. The neutralized solution was kept standing for slow evaporation until a white transparent crystalline separated out (m.p. 416 K). LC-MS/MS: 212 [M+H+], 195, 169, 159, 128, 126, 99, 92 m/z.

Refinement
Hydrogen atom H11 was found in a difference map and refined isotropically. All other H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C-H distances of 0.93-0.97 Å and with U iso (H) = 1.2U eq (C). 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).

Figure 1
The molecular structure of (I) with thermal ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.  The packing of (I) with broken lines to show N-H···O hydrogen bonds. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq