2-Amino-4-(2,4-dichloro­phen­yl)-6-(naphthalen-1-yl)nicotinonitrile

Yuan-Feng Ye; Huai-Qing Wang; Zhi-Qiang Feng

doi:10.1107/S1600536810050609

. 2010 Dec 11;67(Pt 1):o71. doi: 10.1107/S1600536810050609

2-Amino-4-(2,4-dichlorophenyl)-6-(naphthalen-1-yl)nicotinonitrile

Yuan-Feng Ye ^a,^*, Huai-Qing Wang ^a, Zhi-Qiang Feng ^a

PMCID: PMC3050377 PMID: 21522783

Abstract

In the crystal structure of the title compound, C₂₂H₁₃Cl₂N₃, the molecules are connected via intermolecular C—H⋯N and N—H⋯N hydrogen bonds, forming a three-dimensional network. The dihedral angles between naphthyl ring system and the pyridyl and benzene rings are 55.04 (7) and 75.87 (7)°, respectively, whereas the pyridyl and benzene rings are oriented at a dihedral angle of 59.56 (8)°.

Related literature

For the synthetic procedure, see: Mantri et al. (2008 ▶). For the use of the title compound in the preparation of medicines, see: Mkhalid et al. (2006 ▶). For general background to this type of compound, see: Moreau & Huber (1999 ▶).

Experimental

Crystal data

C₂₂H₁₃Cl₂N₃
M _r = 390.25
Triclinic,
a = 9.5020 (19) Å
b = 10.054 (2) Å
c = 10.735 (2) Å
α = 72.78 (3)°
β = 89.17 (3)°
γ = 74.81 (3)°
V = 943.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 293 K
0.30 × 0.10 × 0.10 mm

Data collection

Entaf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.901, T _max = 0.965
3686 measured reflections
3463 independent reflections
2648 reflections with I > 2σ(I)
R _int = 0.014
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.146
S = 1.00
3463 reflections
252 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050609/bq2258sup1.cif

e-67-00o71-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050609/bq2258Isup2.hkl

e-67-00o71-Isup2.hkl^{(169.8KB, hkl)}

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	0.85 (3)	2.19 (3)	3.034 (3)	176 (2)
C4—H4A⋯N3ⁱⁱ	0.93	2.62	3.488 (4)	155

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, and the fund of Jinling Institute of Technology (jit-n-2009–017) for support..

supplementary crystallographic information

Comment

The title compound, C₂₂H₁₃Cl₂N₃,(I), contains amino group, which can react with different groups to prepare various function organic compounds. It is a kind of aromatic organic intermediate which can be used for many fields such as medicine (Mantri et al., 2008). The molecular structure of (I) is shown in Fig. 1. In (I), the naphthyl and the two rings, pyridyl and phenyl are oriented with different dihedral angles; 55.04 (7) ° between naphthyl and pyridyl, 75.87 (7) ° between naphthyl and phenyl and 59.56 (8) ° between pyridyl and phenyl. In the crystal structure of the title compound, the molecules were connected together via N—H···N and C—H···N intermolecular hydrogen bonds to form a three dimensional network, which seems to be very effective in the stabilization of the crystal structure.

Experimental

The title compound, (I) was prepared by the literature method (Mantri et al., 2008). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.5 g) in methanol (20 ml) and evaporating the solvent slowly at room temperature for about 5 d.