2-Amino-4-(2-chlorophenyl)-6-(naphthalen-1-yl)pyridine-3-carbonitrile

In the title compound, C22H14ClN3, prepared by a one-pot reaction under microwave irradiation, the dihedral angles between the central pyridine ring and the pendant naphthyl and chlorobenzene ring systems are 49.2 (2) and 58.2 (3)°, respectively. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R 2 2(8) loops. The pyridine N atom is the acceptor.

In the title compound, C 22 H 14 ClN 3 , prepared by a one-pot reaction under microwave irradiation, the dihedral angles between the central pyridine ring and the pendant naphthyl and chlorobenzene ring systems are 49.2 (2) and 58.2 (3) , respectively. In the crystal, inversion dimers linked by pairs of N-HÁ Á ÁN hydrogen bonds generate R 2 2 (8) loops. The pyridine N atom is the acceptor.

Experimental
For the prepartion of the title compound (1),a mixture of 2-chlorobenzaldehyde (2 mmol), malononitrile (2 mmol), 1naphthal-dehyde (2 mmol) and ammonium acetate (16 mmol) was refluxed under microwave irradiation (6 min, WF-4000M microwave reaction system). After cooling to room temperature, the resulting solid product was filtered off and recrystallized from methanol to give the title compound. Colourless needles were obtained by dissolving the title compound (0.5 g) in methanol (20 ml) and slowly evaporating the solvent at room temperature for a period of about two weeks.

Refinement
All H atoms were positioned geometrically, with C-H = 0.86 Å and N-H = 0.93 Å for aromatic and amino H, and constrained to ride on their parent atoms,with U iso (H) = 1.2U eq (C,N).

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. 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 Cl 0.31710 (12)