2,2′-Dimethyl-4,4′-bipyridine

Bahtier Ibragimov; Edwin Weber; Max Peukert; Conrad Fischer; Wilhelm Seichter

doi:10.1107/S1600536808017807

. 2008 Jun 19;64(Pt 7):o1287. doi: 10.1107/S1600536808017807

2,2′-Dimethyl-4,4′-bipyridine

Bahtier Ibragimov ^a,^*, Edwin Weber ^b, Max Peukert ^b, Conrad Fischer ^b, Wilhelm Seichter ^b

PMCID: PMC2961716 PMID: 21202918

Abstract

In the crystal structure of the title compound, C₁₂H₁₂N₂, the molecule is twisted around the central C—C bond, with a dihedral angle of 8.32 (5)° between the mean planes of the pyridyl rings. The crystal structure is stabilized by arene stacking interactions, with a distance of 3.81 (1) Å between the ring centroids.

Related literature

For related literature, see: Boag et al. (1999 ▶); Kraft et al. (2005 ▶); Leighton & Sanders (1987 ▶); Alcade et al. (2007 ▶); Boghala et al. (2005 ▶); Braunschweig et al. (2006 ▶); Diskin-Posner et al. (2005 ▶); Kryschenko et al. (2003 ▶); Lynch et al. (1999 ▶); Yaghi et al. (1995 ▶).

Experimental

Crystal data

C₁₂H₁₂N₂
M _r = 184.24
Orthorhombic,
a = 11.7961 (3) Å
b = 7.6130 (2) Å
c = 21.2977 (5) Å
V = 1912.61 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 153 (2) K
0.54 × 0.24 × 0.14 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.923, T _max = 0.989
26242 measured reflections
3233 independent reflections
2262 reflections with I > 2σ(I)
R _int = 0.066

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.139
S = 0.91
3233 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-NT (Bruker, 2004 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017807/cs2078sup1.cif

e-64-o1287-sup1.cif^{(15KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017807/cs2078Isup2.hkl

e-64-o1287-Isup2.hkl^{(115.4KB, 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
C6—H6C⋯N1ⁱ	0.98	2.73	3.6728 (16)	161

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the German Research Foundation (DFG) under grant No. We 1016-9/1 is gratefully acknowledged.

supplementary crystallographic information

Comment

The preparation of I was carried out according to the literature procedure (Leighton & Sanders, 1987). The title compound represents a derivative of 4,4'-bipyridine, which is widely used as a bifunctional bridging element for the synthesis of supramolecular assemblies which may be based on hydrogen bond interactions (Lynch et al., 1999, Boghala et al., 2005) or metal coordination complexes (Diskin-Posner et al., 2005, Kryschenko et al., 2003), involving catenanes (Alcade et al., 2007), rotaxanes (Braunschweig et al., 2006) and metal-organic frameworks (Yaghi et al., 1995). In the crystal the title molecule adopts a slightly twisted conformation (see Figure 1), the mean planes of the hetero - aromatic rings make 8.32 (5)° dihedral angle. As there are no good hydrogen bond donors, the N1 nitrogen atom is only involved in the formation of a weak C-H···N hydrogen bond [C6-H6C···N1 distance ca. 2.73 Å]. The packing (Figure 2) is characterized by a columnar arrangement of molecules extending in the direction of the crystallographic b-axis. Within the molecular columns only one of the aromatic rings (designated as A in Fig. 1) of related molecules are involved in "face-to-face" interactions with a centroid···centroid distance of 3.81 (1) Å between such rings.