3,5-Dimeth­oxy-N,N-bis­(2-pyridylmeth­yl)aniline

Hongjuan Li; Xianping Dai; Jufeng Sun

doi:10.1107/S1600536809048685

. 2009 Nov 21;65(Pt 12):o3139. doi: 10.1107/S1600536809048685

3,5-Dimethoxy-N,N-bis(2-pyridylmethyl)aniline

Hongjuan Li ^a,^*, Xianping Dai ^a, Jufeng Sun ^a

PMCID: PMC2971985 PMID: 21578860

Abstract

In the title molecule, C₂₀H₂₁N₃O₂, the benzene ring forms dihedral angles of 80.8 (1) and 83.5 (1)° with the two terminal pyridine rings. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules into chains propagating in [001].

Related literature

For general background to organic ligand-based crystal materials, see: Desiraju (2007 ▶); Moulton & Zaworotko (2001 ▶). For related structures, see: Frisch & Cahil (2008 ▶); Shattock et al. (2008 ▶); Shirman et al. (2008 ▶). graphic file with name e-65-o3139-scheme1.jpg

Experimental

Crystal data

C₂₀H₂₁N₃O₂
M _r = 335.40
Monoclinic,
a = 15.630 (3) Å
b = 5.9562 (12) Å
c = 20.088 (4) Å
β = 111.55 (3)°
V = 1739.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 K
0.27 × 0.25 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.978, T _max = 0.983
14749 measured reflections
4106 independent reflections
3258 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.113
S = 1.10
4106 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048685/cv2657sup1.cif

e-65-o3139-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048685/cv2657Isup2.hkl

e-65-o3139-Isup2.hkl^{(201.2KB, 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
C14—H14⋯O2ⁱ	0.95	2.49	3.3050 (15)	144

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the Binzhou Medical College for financial support (grant No. BY2007KJ13).

supplementary crystallographic information

Comment

In recent years, considerable research has been put into the design and elaboration of new organic ligand-based crystal materials because of their importance in supramolecular chemistry, materials science and solid-state chemistry (Desiraju, 2007; Moulton & Zaworotko, 2001). It is well known that the construction of such materials strongly depends on the nature of organic bridging units. In this regard, considerable attention has been devoted to the design of new functional N-heterocyclic organic bridging units. Among of them, pyridines are useful building blocks, which are frequently employed in the construction of some interesting metal-organic frameworks and organic crystals (Frisch & Cahil, 2008; Shattock et al., 2008; Shirman et al., 2008). Herein, we report a new pyridine compound which could be applied for the preparation of metal-organic and organic crystals.

In the title molecule, (I) (Fig. 1), two pyridine rings form dihedral angles of 80.8 (1) and 83.5 (1)°, respectively, with the central benzene ring. The intermolecular C—H···O interaction (Table 1) links adjacent molecules into chains along the direction [001].

Experimental

3,5-Dimethoxyaniline (73.9 mg, 0.6 mmol) and 5 N NaOH (0.8 ml) were added to the solution of 2-bromomethylprydine (0.525 g, 3.05 mmol) in 1 ml of water, the obtained mixture was stirred vigorously for 24 h at room temperature. Then the mixture was extracted with 15 ml of CH₂Cl₂ for three times and the combined organic layers were dried over anhydrous Na₂SO₄. The crude material was purified by column chromatography on silica gel eluting with petroleum ether/EtOAc (3/1, V/V) to afford the desired product as a yellow solid (0.12 g, 58%). ¹H NMR (400 MHz, CDCl₃): δ = 3.64 (s, 6H), 4.82 (s, 4H), 5.87 (s, 3H), 7.14 (t, J = 6.4 Hz, 2H), 7.29 (s, 2H), 7.64 (t, J = 7.6 Hz, 2H), 8.58 (d, J = 4.4 Hz, 2H).