N 2-(2-Pyrid­yl)-N 6-(4-pyrid­yl)pyridine-2,6-diamine

Zhi-Min Wang; Bo Shao

doi:10.1107/S1600536809033480

. 2009 Aug 29;65(Pt 9):o2273. doi: 10.1107/S1600536809033480

N ²-(2-Pyridyl)-N ⁶-(4-pyridyl)pyridine-2,6-diamine

Zhi-Min Wang ^a,^*, Bo Shao ^a

PMCID: PMC2969993 PMID: 21577668

Abstract

In the title compound, C₁₅H₁₃N₅, the dihedral angles between the central aromatic ring and and the two peripheral rings are 1.5 (6) and 33.1 (4)°. In the crystal, intermolecular N—H⋯N hydrogen bonds connect the molecules into a zigzag chain propagating in [100].

Related literature

For a related structure, see: Huang et al. (2004 ▶). For background to metal-organic framework complexes with polypyridylamine ligands, see: Peng et al. (2000 ▶); Fang et al. (2005 ▶).

Experimental

Crystal data

C₁₅H₁₃N₅
M _r = 263.30
Orthorhombic,
a = 11.4884 (15) Å
b = 7.3445 (10) Å
c = 30.718 (4) Å
V = 2591.9 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.19 × 0.15 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.984, T _max = 0.991
11972 measured reflections
2304 independent reflections
1529 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.187
S = 0.82
2304 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033480/hb5059sup1.cif

e-65-o2273-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033480/hb5059Isup2.hkl

e-65-o2273-Isup2.hkl^{(113.3KB, 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
N4—H4A⋯N1ⁱ	0.86	2.22	3.038 (3)	160
N2—H2A⋯N3ⁱⁱ	0.86	2.35	3.198 (3)	170

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

Acknowledgments

The authors are grateful to Zhejiang Shuren University for financial support.

supplementary crystallographic information

Comment

Metal-organic frameworks complexes with polypyridylamine ligands, bearing diverse networks and special optical and electromagnetic properties (Peng et al., 2000), have aroused great interest among researchers. Tri-pyridyldiamine ligand usually exhibits donor as well as acceptor properties and can be used as a popular chelating ligand (Fang et al., 2005). The crystals of the title compound were obatined unintentionally as the harvested product of the mild reaction of N²-(pydidin-2-yl)-N⁶-(pydidin-4-yl)pyridine-2,6-diamine, zinc salt.

The molecular structure of the title compound is shown in Fig. 1. In the crystal structure, intermoelcular N-H···N hydorgen bonds connect molecules into one-dimensional chain along a axis (Table 1), as shown in Figure 2. The three pyridine rings of the title compound are not coplanar. The dihedral angles between the planes of the central pyridine ring and two peripheral rings are 1.5 (6) and 146.9 (4)° respectively, which is very different from the Cd complex with [2,6-bis(2-pyridylamino)pyridine] [15.6 (5) and 34.1 (3)°] (Huang et al., 2004).

Experimental

N²-(pydidin-2-yl)-N⁶-(pydidin-4-yl)pyridine-2,6-diamine (0.27 mg,0.1 mmol), Zn(CH₃COO)₂ (0.43 mg, 0.1 mmol), were added to dry ethanol. The mixture was heated and stirred for six hours under reflux. The resultant was then filtered off to give a pure solution which was treated by diethyl ether in a closed vessel. Two weeks later, colourless blocks of (I) were obtained.