1,4-Bis[(2-pyridyl­eth­yl)imino­meth­yl]benzene

Haleden Chiririwa; John R Moss; Hong Su; Denver Hendricks; Reinout Meijboom

doi:10.1107/S1600536811009809

. 2011 Mar 19;67(Pt 4):o921. doi: 10.1107/S1600536811009809

1,4-Bis[(2-pyridylethyl)iminomethyl]benzene

Haleden Chiririwa ^a, John R Moss ^a, Hong Su ^a,^*, Denver Hendricks ^b, Reinout Meijboom ^c

PMCID: PMC3099859 PMID: 21754192

Abstract

In the title compound, C₂₂H₂₂N₄, the centroid of the benzene ring is located on an inversion centre. The dihedral angle between the benzene and pyridine rings is 10.94 (5)°. The crystal structure displays weak intermolecular C—H⋯N hydrogen bonding and C—H⋯π interactions.

Related literature

For related compounds, see: Chakraborty et al. (1999 ▶); Haga et al. (1985 ▶).

Experimental

Crystal data

C₂₂H₂₂N₄
M _r = 342.44
Monoclinic,
a = 6.0078 (6) Å
b = 26.023 (3) Å
c = 6.1319 (7) Å
β = 106.009 (2)°
V = 921.47 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.26 × 0.24 × 0.17 mm

Data collection

Bruker Kappa DUO APEXII diffractometer
11941 measured reflections
2288 independent reflections
1945 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.110
S = 1.06
2288 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009809/go2006sup1.cif

e-67-0o921-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009809/go2006Isup2.hkl

e-67-0o921-Isup2.hkl^{(112.5KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the C1–C5/N1 and C9–C11/C9′–C11′ rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1ⁱ	0.95	2.74	3.544 (3)	143 (3)
C4—H4⋯N2ⁱ	0.95	2.69	3.593 (2)	159 (4)
C7—H7A⋯N1ⁱⁱ	0.99	2.87	3.847 (2)	171 (5)
C2—H2⋯Cg1ⁱⁱⁱ	0.95	2.88	3.826 (4)	172 (5)
C6—H6A⋯Cg2^iv	0.99	2.90	3.508 (3)	120 (2)

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

Acknowledgments

We gratefully acknowledge Mintek and Project AuTEK for funding this project.

supplementary crystallographic information

Comment

This work originates from our interest in developing a new class of tetradentate ligands. To the best of our knowledge, this work demonstrates the first example of neutral pyridinyldimine-based bridging ligand. The title compound might be expected to behave as a tetradentate chelating agent, in which both of the N atoms from the imine might coordinate, along with the two pyridinyl N atoms. Chakraborty et al. (1999) reported coordination of similar ligands to ruthenium whilst Haga and Koizumi (1985) reported their coordination to molybdenum. The structure of the title compound crystallized in space group P2₁/n with Z = 2. The molecule, shown in Fig. 1, has a center of inversion at the centroid of the benzene ring and was located in special positions at Wyckoff positon a. The conformation of the molecule is best described by the dihedral angle of the central ring and pyridyl ring of 10.94 (5)°. The structure is stabilized by weak hydrogen bonds of the type C—H···N and C—H···π, the metrics of which are given in Table 1. The C—H···N intermolecular interactions, as well as C6—H6A···Ring 1 (of C10—C9—C11—C10'-C9'-C11'), connect the parallel neighbouring molecules into 2-dimentional layers. And these layers are then linked along the b axis into 3-dimentional herringbone packing via C2—H2···Ring 2 (of C1—C2—C3—C4—C5—N1) interactions, as shown in Fig.2.

Experimental

The title compound was synthesized as follows: a solution of benzene 1,4-dicarboxaldehyde (0.50 g, 3.73 mmol) in methanol (10 ml) was added dropwise to a stirred solution of 2-(pyridin-2-yl)ethanamine(0.91 g, 7.42 mmol) in methanol (10 ml). The mixture was stirred at room temperature for ca 16 h. The precipitate was filtered off and washed with diethylether and dried under vacuum for 4 h affording a fine shiny white powder in 85% yield. M.p.: does not melt below 260 °C. Recrystallization by slow diffusion of Et₂O into a concentrated CH₂Cl₂ of the solution gave colorless crystals suitable for X-ray structure analysis.