N-(Pyridin-2-ylmeth­yl)pyridin-2-amine

Suk-Hee Moon; Tae Ho Kim; Ki-Min Park

doi:10.1107/S1600536811016874

. 2011 May 7;67(Pt 6):o1355. doi: 10.1107/S1600536811016874

N-(Pyridin-2-ylmethyl)pyridin-2-amine

Suk-Hee Moon ^a, Tae Ho Kim ^b,^*, Ki-Min Park ^b,^*

PMCID: PMC3120475 PMID: 21754749

Abstract

The title compound, C₁₁H₁₁N₃, crystallizes with two molecules (A and B) in the asymmetric unit. The geometries of both molecules are very similar, with the exception of the torsion angles of the inter-ring chains; the values for C—N—C—C are 67.4 (5) and −69.3 (5)° for molecules A and B, respectively. The dihedral angles between the pyridyl ring planes are 84.0 (2) and 83.2 (2)° for molecules A and B, respectively. In the crystal, weak intermolecular N—H⋯N hydrogen bonds and C—H⋯π interactions contribute to the stabilization of the packing.

Related literature

For details of the synthesis, see: Foxon et al. (2002 ▶). For the crystal structures of Cu complexes of the title compound, see: Lee et al. (2008 ▶).

Experimental

Crystal data

C₁₁H₁₁N₃
M _r = 185.23
Orthorhombic,
a = 14.5434 (14) Å
b = 5.8198 (6) Å
c = 23.045 (2) Å
V = 1950.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.45 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer
11034 measured reflections
2182 independent reflections
1814 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.124
S = 1.10
2182 reflections
253 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016874/wn2432sup1.cif

e-67-o1355-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016874/wn2432Isup2.hkl

e-67-o1355-Isup2.hkl^{(107.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811016874/wn2432Isup3.cml

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

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

Cg1, Cg2 and Cg3 are the centroids of the N4/C12–C16, N2/C7–C11 and N5/C18–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯N4	0.89	2.14	3.019 (5)	172
N6—H6N⋯N1	0.93	2.10	3.012 (5)	168
C1—H1⋯Cg1ⁱ	0.95	2.77	3.53	137
C3—H3⋯Cg2ⁱⁱ	0.95	2.85	3.69	147
C14—H14⋯Cg3ⁱⁱⁱ	0.95	2.65	3.51	149

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

Acknowledgments

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2010–0022675).

supplementary crystallographic information

Comment

The title compound was prepared for use as a multidentate ligand in the formation of metallosupramolecules according to a published literature procedure (Foxon et al., 2002). The crystal structures of Cu complexes of the title compound have already been reported (Lee et al., 2008). However the crystal structure of the free form has not yet been reported.

The title compound (Scheme, Fig. 1) crystallized in the non-centrosymmetric space group Pca2₁. The asymmetric unit contains two crystallographically independent molecules (A and B). The geometries of both molecules are very similar, with the exception of the torsion angles of the inter-ring chains; the value for C5—N3—C6—C7 is 67.4 (5) ° and for C16—N6—C17—C18 is -69.3 (5) °. The dihedral angles between the pyridyl ring planes are 84.0 (2)° and 83.2 (2) ° for molecules A and B, respectively.

In the crystal structure, the amine groups of both molecules are involved in pair-wise intermolecular N—H···N interactions, leading to the formation of dimers (Table 1, Fig. 1, Fig. 2). Weak intermolecular C—H···π interactions are also present (Fig. 2). These intermolecular interactions contribute to the stabilization of the packing.

Experimental

The title compound was synthesized according to a literature procedure (Foxon et al., 2002). Slow evaporation of a solution in CH₃OH gave single crystals suitable for X-ray analysis.