organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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2,2′-Di­methyl-4,4′-bi­pyridine

aInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, H. Abdullaev 83, Tashkent 100125, Uzbekistan, and bInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
*Correspondence e-mail: bahtier@academy.uzsci.net

(Received 7 May 2008; accepted 12 June 2008; online 19 June 2008)

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[Boag, N. M., Coward, K. M., Jones, A. C., Pemble, M. E. & Thompson, J. R. (1999). Acta Cryst. C55, 672-674.]); Kraft et al. (2005[Kraft, T. S., Hanuschek, E., Beckhaus, R., Haase, D. & Saak, W. (2005). Chem. Eur. J. 11, 969-978.]); Leighton & Sanders (1987[Leighton, P. & Sanders, J. K. M. (1987). J. Chem. Soc. Perkin Trans. 1, pp. 2385-2393.]); Alcade et al. (2007[Alcade, E., Perez-Garcia, L., Ramos, S., Stoddart, J. F., White, A. J. P. & Williams, D. J. (2007). Chem. Eur. J. 13, 3964-3979.]); Boghala et al. (2005[Boghala, B. R., Basavoju, S. & Nangia, A. (2005). CrystEngComm, 7, 551-562.]); Braunschweig et al. (2006[Braunschweig, A. B., Ronconi, C. M., Ja-Young Han, Arico, F., Cantrill, S. J., Stoddart, J. F., Khan, S. I., White, A. J. P., & Williams, D. J. (2006). Eur. J. Org. Chem. pp. 1857-1866.]); Diskin-Posner et al. (2005[Diskin-Posner, Y., Patra, G. K. & Goldberg, I. (2005). Chem. Commun. pp. 1420-1421.]); Kryschenko et al. (2003[Kryschenko, Y. K., Seidel, S. R., Arif, A. M. & Stang, P. (2003). J. Am. Chem. Soc. 125, 5193-5198.]); Lynch et al. (1999[Lynch, D. E., Chatwin, S. & Parsons, S. (1999). Cryst. Eng. 2, 137-144.]); Yaghi et al. (1995[Yaghi, O. M., & Hailian Li (1995). J. Am. Chem. Soc. 117, 10401-10402.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12N2

  • Mr = 184.24

  • Orthorhombic, P b c a

  • 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[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.923, Tmax = 0.989

  • 26242 measured reflections

  • 3233 independent reflections

  • 2262 reflections with I > 2σ(I)

  • Rint = 0.066

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6C⋯N1i 0.98 2.73 3.6728 (16) 161
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT-NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-NT (Bruker, 2004[Bruker (2004). APEX2 and SAINT-NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

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.

Related literature top

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, Patra & Goldberg (2005); Kryschenko et al. (2003); Lynch et al. (1999); Yaghi et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-NT (Bruker, 2004); data reduction: SAINT-NT (Bruker, 2004); 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).

Figures top
[Figure 1] Fig. 1. Molecular presentation of the title compound with atomic labels and 50% probability displacement ellipsoids for non H-atoms.
[Figure 2] Fig. 2. Packing diagram as viewed down the crystallographic b axis.
2,2'-Dimethyl-4,4'-bipyridine top
Crystal data top
C12H12N2F(000) = 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 = 2.6–31.2°
b = 7.6130 (2) ŵ = 0.08 mm1
c = 21.2977 (5) ÅT = 153 K
V = 1912.61 (8) Å3Needle, colourless
Z = 80.54 × 0.24 × 0.14 mm
Data collection top
Bruker X8 APEXII CCD area-detector
diffractometer
3233 independent reflections
Radiation source: fine-focus sealed tube2262 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
ϕ and ω scansθmax = 31.7°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1717
Tmin = 0.924, Tmax = 0.989k = 1011
26242 measured reflectionsl = 3128
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 0.91 w = 1/[σ2(Fo2) + (0.0856P)2]
where P = (Fo2 + 2Fc2)/3
3233 reflections(Δ/σ)max < 0.001
129 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C12H12N2V = 1912.61 (8) Å3
Mr = 184.24Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.7961 (3) ŵ = 0.08 mm1
b = 7.6130 (2) ÅT = 153 K
c = 21.2977 (5) Å0.54 × 0.24 × 0.14 mm
Data collection top
Bruker X8 APEXII CCD area-detector
diffractometer
3233 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2262 reflections with I > 2σ(I)
Tmin = 0.924, Tmax = 0.989Rint = 0.066
26242 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 0.91Δρmax = 0.37 e Å3
3233 reflectionsΔρmin = 0.26 e Å3
129 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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*
H6C1.01150.00790.44040.042*
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)
H100.51480.18760.22570.030*
C110.58594 (8)0.07721 (13)0.30182 (5)0.0220 (2)
H110.66180.10610.29090.026*
C120.24104 (9)0.02673 (16)0.34184 (6)0.0288 (3)
H12A0.21110.11280.31190.043*
H12B0.23270.07210.38470.043*
H12C0.19900.08370.33780.043*
Atomic displacement parameters (Å2) top
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, º) top
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—C3178.28 (9)C2—C1—C7—C8172.52 (9)
C4—N1—C3—C20.45 (15)C11—C7—C8—C90.41 (14)
C4—N1—C3—C6179.03 (9)C1—C7—C8—C9178.39 (9)
C1—C2—C3—N11.18 (15)C10—N2—C9—C81.31 (15)
C1—C2—C3—C6178.28 (9)C10—N2—C9—C12178.16 (9)
C3—N1—C4—C50.55 (16)C7—C8—C9—N21.35 (15)
N1—C4—C5—C10.80 (17)C7—C8—C9—C12178.10 (9)
C2—C1—C5—C40.05 (15)C9—N2—C10—C110.42 (17)
C7—C1—C5—C4179.20 (9)N2—C10—C11—C70.46 (17)
C5—C1—C7—C11170.38 (9)C8—C7—C11—C100.43 (14)
C2—C1—C7—C118.74 (14)C1—C7—C11—C10179.24 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6C···N1i0.982.733.6728 (16)161
Symmetry code: (i) x+2, y, z+1.

Experimental details

Crystal data
Chemical formulaC12H12N2
Mr184.24
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)153
a, b, c (Å)11.7961 (3), 7.6130 (2), 21.2977 (5)
V3)1912.61 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.54 × 0.24 × 0.14
Data collection
DiffractometerBruker X8 APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.924, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
26242, 3233, 2262
Rint0.066
(sin θ/λ)max1)0.740
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.139, 0.91
No. of reflections3233
No. of parameters129
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.26

Computer programs: APEX2 (Bruker, 2004), SAINT-NT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6C···N1i0.982.733.6728 (16)161
Symmetry code: (i) x+2, y, z+1.
 

Acknowledgements

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

References

First citationAlcade, E., Perez-Garcia, L., Ramos, S., Stoddart, J. F., White, A. J. P. & Williams, D. J. (2007). Chem. Eur. J. 13, 3964–3979.  PubMed Google Scholar
First citationBoag, N. M., Coward, K. M., Jones, A. C., Pemble, M. E. & Thompson, J. R. (1999). Acta Cryst. C55, 672–674.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationBoghala, B. R., Basavoju, S. & Nangia, A. (2005). CrystEngComm, 7, 551–562.  Google Scholar
First citationBraunschweig, A. B., Ronconi, C. M., Ja-Young Han, Arico, F., Cantrill, S. J., Stoddart, J. F., Khan, S. I., White, A. J. P., & Williams, D. J. (2006). Eur. J. Org. Chem. pp. 1857–1866.  Web of Science CSD CrossRef Google Scholar
First citationBruker (2004). APEX2 and SAINT-NT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDiskin-Posner, Y., Patra, G. K. & Goldberg, I. (2005). Chem. Commun. pp. 1420–1421.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationKraft, T. S., Hanuschek, E., Beckhaus, R., Haase, D. & Saak, W. (2005). Chem. Eur. J. 11, 969–978.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationKryschenko, Y. K., Seidel, S. R., Arif, A. M. & Stang, P. (2003). J. Am. Chem. Soc. 125, 5193–5198.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationLeighton, P. & Sanders, J. K. M. (1987). J. Chem. Soc. Perkin Trans. 1, pp. 2385–2393.  CrossRef Web of Science Google Scholar
First citationLynch, D. E., Chatwin, S. & Parsons, S. (1999). Cryst. Eng. 2, 137–144.  CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYaghi, O. M., & Hailian Li (1995). J. Am. Chem. Soc. 117, 10401–10402.  CrossRef CAS Google Scholar

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