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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1287.
Published online 2008 June 19. doi:  10.1107/S1600536808017807
PMCID: PMC2961716

2,2′-Dimethyl-4,4′-bipyridine

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 [triangle]); Kraft et al. (2005 [triangle]); Leighton & Sanders (1987 [triangle]); Alcade et al. (2007 [triangle]); Boghala et al. (2005 [triangle]); Braunschweig et al. (2006 [triangle]); Diskin-Posner et al. (2005 [triangle]); Kryschenko et al. (2003 [triangle]); Lynch et al. (1999 [triangle]); Yaghi et al. (1995 [triangle]).

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Object name is e-64-o1287-scheme1.jpg

Experimental

Crystal data

  • C12H12N2
  • M r = 184.24
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1287-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.26 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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.

Figures

Fig. 1.
Molecular presentation of the title compound with atomic labels and 50% probability displacement ellipsoids for non H-atoms.
Fig. 2.
Packing diagram as viewed down the crystallographic b axis.

Crystal data

C12H12N2F000 = 784
Mr = 184.24Dx = 1.280 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5227 reflections
a = 11.7961 (3) Åθ = 2.6–31.2º
b = 7.6130 (2) ŵ = 0.08 mm1
c = 21.2977 (5) ÅT = 153 (2) K
V = 1912.61 (8) Å3Needle, colourless
Z = 80.54 × 0.24 × 0.14 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer3233 independent reflections
Radiation source: fine-focus sealed tube2262 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.066
T = 153(2) Kθmax = 31.7º
[var phi] and ω scansθmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −17→17
Tmin = 0.924, Tmax = 0.989k = −10→11
26242 measured reflectionsl = −31→28

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.139  w = 1/[σ2(Fo2) + (0.0856P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
3233 reflectionsΔρmax = 0.37 e Å3
129 parametersΔρmin = −0.25 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.83087 (7)0.16449 (12)0.48415 (4)0.0253 (2)
N20.38746 (7)−0.09210 (12)0.27478 (4)0.0235 (2)
C10.65454 (8)0.06887 (12)0.40087 (5)0.0179 (2)
C20.76889 (8)0.05080 (13)0.38471 (5)0.0206 (2)
H20.78890.00620.34460.025*
C30.85371 (8)0.09788 (13)0.42717 (5)0.0215 (2)
C40.72102 (9)0.18301 (15)0.49892 (5)0.0269 (2)
H40.70340.23100.53890.032*
C50.63117 (8)0.13748 (14)0.46021 (5)0.0230 (2)
H50.55510.15270.47380.028*
C60.97634 (9)0.07391 (15)0.41063 (6)0.0278 (2)
H6A1.01520.18750.41270.042*
H6B0.98250.02650.36800.042*
H6C1.0115−0.00790.44040.042*
C70.56279 (8)0.01492 (12)0.35706 (5)0.0175 (2)
C80.44859 (8)0.05087 (13)0.36967 (5)0.0194 (2)
H80.42850.11390.40650.023*
C90.36413 (8)−0.00544 (13)0.32832 (5)0.0206 (2)
C100.49692 (8)−0.12586 (15)0.26316 (5)0.0247 (2)
H100.5148−0.18760.22570.030*
C110.58594 (8)−0.07721 (13)0.30182 (5)0.0220 (2)
H110.6618−0.10610.29090.026*
C120.24104 (9)0.02673 (16)0.34184 (6)0.0288 (3)
H12A0.21110.11280.31190.043*
H12B0.23270.07210.38470.043*
H12C0.1990−0.08370.33780.043*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0222 (4)0.0285 (5)0.0252 (5)0.0012 (3)−0.0059 (4)−0.0026 (3)
N20.0210 (4)0.0277 (5)0.0218 (5)−0.0023 (3)−0.0015 (3)−0.0032 (3)
C10.0165 (4)0.0192 (4)0.0179 (5)−0.0005 (3)−0.0014 (3)0.0009 (3)
C20.0178 (4)0.0245 (5)0.0196 (5)−0.0002 (3)−0.0006 (4)−0.0001 (3)
C30.0185 (4)0.0220 (5)0.0241 (5)−0.0006 (3)−0.0034 (4)0.0030 (4)
C40.0250 (5)0.0343 (6)0.0214 (5)0.0027 (4)−0.0038 (4)−0.0068 (4)
C50.0198 (4)0.0290 (5)0.0201 (5)0.0010 (4)−0.0012 (4)−0.0027 (4)
C60.0173 (5)0.0353 (6)0.0310 (6)0.0003 (4)−0.0031 (4)0.0008 (4)
C70.0164 (4)0.0191 (4)0.0170 (5)−0.0013 (3)−0.0009 (3)0.0021 (3)
C80.0172 (4)0.0221 (5)0.0189 (5)0.0002 (3)−0.0005 (3)−0.0017 (3)
C90.0173 (4)0.0230 (5)0.0214 (5)−0.0002 (3)−0.0018 (4)0.0001 (4)
C100.0230 (5)0.0313 (5)0.0197 (5)−0.0019 (4)0.0011 (4)−0.0053 (4)
C110.0182 (4)0.0281 (5)0.0196 (5)−0.0006 (3)0.0012 (4)−0.0025 (4)
C120.0176 (5)0.0371 (6)0.0316 (6)0.0027 (4)−0.0023 (4)−0.0076 (5)

Geometric parameters (Å, °)

N1—C41.3408 (13)C6—H6B0.9800
N1—C31.3426 (14)C6—H6C0.9800
N2—C101.3395 (13)C7—C111.3967 (14)
N2—C91.3459 (13)C7—C81.4006 (13)
C1—C51.3949 (14)C8—C91.3971 (14)
C1—C21.3989 (13)C8—H80.9500
C1—C71.4868 (13)C9—C121.5004 (13)
C2—C31.3955 (14)C10—C111.3848 (14)
C2—H20.9500C10—H100.9500
C3—C61.5000 (14)C11—H110.9500
C4—C51.3869 (14)C12—H12A0.9800
C4—H40.9500C12—H12B0.9800
C5—H50.9500C12—H12C0.9800
C6—H6A0.9800
C4—N1—C3116.47 (9)H6B—C6—H6C109.5
C10—N2—C9116.59 (9)C11—C7—C8116.59 (9)
C5—C1—C2116.77 (9)C11—C7—C1121.67 (9)
C5—C1—C7121.88 (9)C8—C7—C1121.73 (9)
C2—C1—C7121.35 (9)C9—C8—C7120.34 (9)
C3—C2—C1120.44 (10)C9—C8—H8119.8
C3—C2—H2119.8C7—C8—H8119.8
C1—C2—H2119.8N2—C9—C8122.59 (9)
N1—C3—C2122.61 (9)N2—C9—C12116.14 (9)
N1—C3—C6116.85 (9)C8—C9—C12121.27 (9)
C2—C3—C6120.53 (10)N2—C10—C11124.74 (10)
N1—C4—C5124.94 (10)N2—C10—H10117.6
N1—C4—H4117.5C11—C10—H10117.6
C5—C4—H4117.5C10—C11—C7119.13 (9)
C4—C5—C1118.76 (10)C10—C11—H11120.4
C4—C5—H5120.6C7—C11—H11120.4
C1—C5—H5120.6C9—C12—H12A109.5
C3—C6—H6A109.5C9—C12—H12B109.5
C3—C6—H6B109.5H12A—C12—H12B109.5
H6A—C6—H6B109.5C9—C12—H12C109.5
C3—C6—H6C109.5H12A—C12—H12C109.5
H6A—C6—H6C109.5H12B—C12—H12C109.5
C5—C1—C2—C30.87 (14)C5—C1—C7—C88.36 (15)
C7—C1—C2—C3−178.28 (9)C2—C1—C7—C8−172.52 (9)
C4—N1—C3—C20.45 (15)C11—C7—C8—C90.41 (14)
C4—N1—C3—C6−179.03 (9)C1—C7—C8—C9−178.39 (9)
C1—C2—C3—N1−1.18 (15)C10—N2—C9—C81.31 (15)
C1—C2—C3—C6178.28 (9)C10—N2—C9—C12−178.16 (9)
C3—N1—C4—C50.55 (16)C7—C8—C9—N2−1.35 (15)
N1—C4—C5—C1−0.80 (17)C7—C8—C9—C12178.10 (9)
C2—C1—C5—C40.05 (15)C9—N2—C10—C11−0.42 (17)
C7—C1—C5—C4179.20 (9)N2—C10—C11—C7−0.46 (17)
C5—C1—C7—C11−170.38 (9)C8—C7—C11—C100.43 (14)
C2—C1—C7—C118.74 (14)C1—C7—C11—C10179.24 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6C···N1i0.982.733.6728 (16)161

Symmetry codes: (i) −x+2, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2078).

References

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