N,N′-Dimethyl-N,N′-bis­(pyridin-2-yl)methane­diamine

Moon-Sun Lee; Minyoung Yoon; O-bong Yang; Dong-Heon Lee; Gyungse Park

doi:10.1107/S1600536811046320

. 2011 Nov 9;67(Pt 12):o3226. doi: 10.1107/S1600536811046320

N,N′-Dimethyl-N,N′-bis(pyridin-2-yl)methanediamine

Moon-Sun Lee ^a, Minyoung Yoon ^b, O-bong Yang ^c, Dong-Heon Lee ^a,^*, Gyungse Park ^d,^*

PMCID: PMC3238888 PMID: 22199741

Abstract

The title compound, C₁₃H₁₆N₄, consists of two pyridine rings which are linked by an N,N′-dimethylmethaneamine chain. The pyridine rings adopt a twist conformation and the dihedral angle between them is 60.85 (5)°. The crystal packing is stabilized by weak C—H⋯π interactions.

Related literature

For the synthesis of the title compound, see: Kahn et al. (1945 ▶). For applications of heteroaromatic amines, see: Mehrkhodavandi & Schrock (2001 ▶); Hall et al. (1998 ▶); Lee (2003 ▶).

Experimental

Crystal data

C₁₃H₁₆N₄
M _r = 228.30
Monoclinic,
a = 11.6652 (7) Å
b = 8.3921 (5) Å
c = 12.8966 (7) Å
β = 106.634 (2)°
V = 1209.69 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.12 × 0.08 × 0.08 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.963, T _max = 0.986
27844 measured reflections
2516 independent reflections
2105 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.125
S = 0.96
2516 reflections
218 parameters
All H-atom parameters refined
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811046320/bx2378sup1.cif

e-67-o3226-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046320/bx2378Isup2.hkl

e-67-o3226-Isup2.hkl^{(123.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811046320/bx2378Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the N1/C1–C5 and N4/C9–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cg2ⁱ	0.99 (2)	2.64 (2)	3.484 (1)	143 (1)
C6—H7⋯Cg2ⁱⁱ	1.00 (2)	2.75 (2)	3.545 (2)	137 (1)
C10—H13⋯Cg1ⁱⁱⁱ	0.95 (2)	2.90 (1)	3.637 (1)	135 (1)

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

Acknowledgments

This work was supported by the "Human Resource Development (project name: Advanced track for Si-based solar cell materials and devices, project No. 201040100660)" of the Korea Institute of Energy Technology Evaluation and Planning (KETEP) grant funded by the Korean Government Ministry of Knowledge Economy.

supplementary crystallographic information

Comment

Heteroaromatic amines based metal complexes have been extensively studied due to their numerous potential applications as catalysts, drugs, biomimetic chemistry, and so on. (Mehrkhodavandi, et al., (2001) , Hall, et al.,(1998), Lee, (2003). We are interested in the use of chelates containing pyridylamine. We report here the crystal structure of the title compound, Fig. 1, which consists of two 2-pyridyl rings which are linked together by a N,N'-dimethylmethaneamine chain .The pyridine rings adopt a twist conformation and the dihedral angle between them is 60.85 (5)°. The crystal packing is stabilized by weak C—H···π interactions, Fig. 2, Table 1.

Experimental

N,N'-dimethyl-N,N'-di(pyridin-2-yl)methanediamine was prepared by a reported method, Kahn, et al., (1945). A solution of 2-(methylamino)pyridine (5.00 g, 4.62 × 10 ^-2 mol) in water (50 ml) was added dropwise to 37% formaldehyde solution (1.83 ml, 2.31 × 10^-2mol) at 0°C. The reation mixture was stirred at room temperature for overnight and the white precipitate formed was filtered,washed with water and dried. It was dissolved in acetone, dried over MgSO₄ and concentrated. It was recrystallized in acetonitrile. Yield: 92% (4.88 g)