2-Amino-6-{[(6-chloropyridin-3-yl)methyl](ethyl)amino}-1-methyl-5-nitro-4-phenyl-1,4-dihydropyridine-3-carbonitrile ethanol monosolvate

In the title compound, C21H21ClN6O2·C2H6O, a member of the insecticidal active neonicotinoid group of compounds, the 1,4-dihydropyridine ring adopts a boat conformation. An intramolecular C—H⋯O hydrogen bond occurs while the components are linked by an N—H⋯O interaction. The crystal packing is stablized by O—H⋯N hydrogen bonds and C—H⋯O interactions.

In the title compound, C 21 H 21 ClN 6 O 2 ÁC 2 H 6 O, a member of the insecticidal active neonicotinoid group of compounds, the 1,4dihydropyridine ring adopts a boat conformation. An intramolecular C-HÁ Á ÁO hydrogen bond occurs while the components are linked by an N-HÁ Á ÁO interaction. The crystal packing is stablized by O-HÁ Á ÁN hydrogen bonds and C-HÁ Á ÁO interactions.   Table 1 Hydrogen-bond geometry (Å , ). gaining widespread use as a way to control pests, because of their high potency and low mammalian toxicity. As part of the chloronicotinyl subclass, nitenpyram, which was brought to the market two decades ago, also showed higher selectivity and better systemic properties against mammals, birds, aquatic life than insects, due to the differential binding affinities with the nAChR receptors of their neurosystem. (Jeschke & Nauen, 2008;Tomizawa & Casida, 2009;Minamida et al., 1993;Kashiwada, 1996;Shao et al., 2008;Elbert & Nauen, 2000). In this report, the title compound (Scheme I) was synthesized and characterized by X-ray diffraction.
The crystal packing is stablized by O-H···N, N-H···O and C-H···O hydrogen bonds (Fig. 2). Analysis shows that no intermolecular p···π or C-H···π interactions exist in the crystal structure.

Experimental
The title compound was prepared by the literature method (Zhang et al., 2010)

Refinement
During the refinement, the ethanol molecule was disordered over two sites. These C-C and C-O distances were refined with the restraints of C-C = 1.51 (1)Å and C-O = 1.38 (1)Å by using the DFIX command. The final occupancies for the major and minor components were 0.57 (1):0.43 (1), respectively. In (I), H atoms bonded to C and N atoms were located supplementary materials at their ideal positions and subsequently treated as riding modes with C-H distances of 0.93Å (aromatic), 0.97Å (methylene) 0.98Å (methine) 0.86Å (amine) and 0.96Å (methyl) with U iso (H) = 1.2U eq (aromatic, methylene, methine C or N) or 1.5U eq (methyl C). H atoms bonded to ethanol O atoms were located at its ideal position (O-H=0.82Å) and refined with the constraint of the U iso (H) = 1.5U eq (O).    Part of the crystal packing in the title compound (I). Hydrogen bonds are shown as dashed lines. Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 Occ. (