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

Hong-Xia Wei; Jing Zhu; Ming Li; Jian-qiang Wang; Cheng Guo

doi:10.1107/S1600536812020909

. 2012 May 23;68(Pt 6):o1839. doi: 10.1107/S1600536812020909

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

Hong-Xia Wei ^a, Jing Zhu ^a, Ming Li ^a, Jian-qiang Wang ^a, Cheng Guo ^b,^*

PMCID: PMC3379409 PMID: 22719607

Abstract

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.

Related literature

For the use of 2-amino-3-cyanopyridines as intermediates in the preparation of heterocyclic compounds, see: Shishoo et al. (1983 ▶). For the synthesis, see: Mantri et al. (2008 ▶). For related structures, see: Mkhalid et al. (2006 ▶). graphic file with name e-68-o1839-scheme1.jpg

Experimental

Crystal data

C₂₂H₁₄ClN₃
M _r = 355.81
Monoclinic,
a = 12.275 (3) Å
b = 4.6490 (9) Å
c = 30.887 (6) Å
β = 90.18 (3)°
V = 1762.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.956, T _max = 0.978
3397 measured reflections
3236 independent reflections
1558 reflections with I > 2σ(I)
R _int = 0.057
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.185
S = 1.00
3236 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020909/hb6750sup1.cif

e-68-o1839-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020909/hb6750Isup2.hkl

e-68-o1839-Isup2.hkl^{(158.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812020909/hb6750Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1ⁱ	0.86	2.23	3.086 (5)	176

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The title compound, C₂₂H₁₄ClN₃(1), is an intermediate in the synthesis of biologically active molecules (Shishoo et al., 1983; Mantri et al. 2008). Herein we report its crystal structure. The molecular structure of (I) is shown in Fig. 1, and the selected geometric parameters are given in Table 1. In the molecules,the naphthyl (C13—C22) and phenyl ring planes (C1—C6) form torsion angles 49.2 and 58.2 °, respectively, with the middle pyridyl ring plane. In the crystal, there are N—H···N hydrogen bonds, which connect the independent molecules into dimers (Fig. 2 and Tab. 1).

Experimental

For the prepartion of the title compound (1),a mixture of 2-chlorobenzaldehyde (2 mmol), malononitrile (2 mmol), 1-naphthal-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.