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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1586.
Published online 2009 June 17. doi:  10.1107/S1600536809019151
PMCID: PMC2969272

5,5′-Dimethyl-2,2′-bipyridine

Abstract

The asymmetric unit of the title compound, C12H12N2, contains two half-mol­ecules related by an inversion center, the planes of their pyridine rings being oriented at a dihedral angle of 69.62 (4)°. In the crystal structure, a π–π contact between the pyridine rings [centroid–centroid distance = 3.895 (3) Å] may stabilize the structure. A weak C—H(...)π inter­action is also found.

Related literature

For related structures, see: Ahmadi et al. (2008 [triangle]); Albada et al. (2004 [triangle]); Amani et al. (2007 [triangle]); Kalateh et al. (2008 [triangle]); Khalighi et al. (2008 [triangle]); Maheshwari et al. (2007 [triangle]); Tadayon Pour et al. (2008 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-o1586-scheme1.jpg

Experimental

Crystal data

  • C12H12N2
  • M r = 184.24
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1586-efi1.jpg
  • a = 6.409 (4) Å
  • b = 7.312 (5) Å
  • c = 11.533 (8) Å
  • α = 96.04 (5)°
  • β = 91.16 (4)°
  • γ = 105.03 (5)°
  • V = 518.4 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 298 K
  • 0.50 × 0.41 × 0.29 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 6191 measured reflections
  • 2739 independent reflections
  • 2067 reflections with I > 2σ(I)
  • R int = 0.082

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.205
  • S = 1.08
  • 2739 reflections
  • 129 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019151/hk2693sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019151/hk2693Isup2.hkl

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

Acknowledgments

We are grateful to Damghan University of Basic Sciences for financial support.

supplementary crystallographic information

Comment

5,5'-Dimethyl-2,2'-bipyridine, (5,5'-dmbipy), is a good bidentate ligand, and numerous complexes with 5,5'-dmbipy have been prepared, such as that of zinc (Khalighi et al., 2008), mercury (Tadayon Pour et al., 2008), iron (Amani et al., 2007), indium (Kalateh et al., 2008), cadmium (Ahmadi et al., 2008), copper (Albada et al., 2004) and platin (Maheshwari et al., 2007). We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig.1) contains two halves molecules, in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (N1/C1-C4/C6) and B (N2/C7-C10/C12) are, of course, planar and they are oriented at a dihedral angle of A/B = 69.62 (4)°.

In the crystal structure (Fig. 2), the π–π contact between the pyridine rings, Cg2—Cg2i [symmetry code: (i) 1 - x, 2 - y, 2 - z, where Cg2 is centroid of the ring B (N2/C7-C10/C12)] may stabilize the structure, with a centroid-centroid distance of 3.895 (3) Å. There also exists a weak C—H···π interaction (Table 1).

Experimental

For the preparation of the title compound, a solution of 5,5'-dimethyl-2,2' -bipyridine (0.15 g, 0.80 mmol) in methanol (15 ml) was added to a solution of BaCl2.2H2O, (0.10 g, 0.40 mmol) in water (5 ml) and the resulting colorless solution was stirred for 10 min at 313 K. Then, it was left to evaporate slowly at room temperature. After one week, colorless prismatic crystals of the title compound were isolated.

Refinement

H atoms were positioned geometrically, with C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry codes: (a) 1 - x, 2 - y, 1 - z, (b) -x, 2 - y, 2 - z].
Fig. 2.
A partial packing diagram of the title compound.

Crystal data

C12H12N2Z = 2
Mr = 184.24F(000) = 196
Triclinic, P1Dx = 1.180 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.409 (4) ÅCell parameters from 1133 reflections
b = 7.312 (5) Åθ = 1.8–29.3°
c = 11.533 (8) ŵ = 0.07 mm1
α = 96.04 (5)°T = 298 K
β = 91.16 (4)°Prism, colorless
γ = 105.03 (5)°0.50 × 0.41 × 0.29 mm
V = 518.4 (6) Å3

Data collection

Bruker SMART CCD area-detector diffractometer2067 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.082
graphiteθmax = 29.3°, θmin = 1.8°
[var phi] and ω scansh = −8→8
6191 measured reflectionsk = −10→10
2739 independent reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.1057P)2 + 0.0566P] where P = (Fo2 + 2Fc2)/3
2739 reflections(Δ/σ)max = 0.002
129 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.24 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
N10.4778 (2)0.76393 (19)0.53822 (13)0.0604 (4)
N20.0741 (2)0.77876 (19)0.99037 (14)0.0656 (4)
C10.4223 (2)0.92544 (19)0.52837 (12)0.0486 (3)
C20.2280 (2)0.9529 (2)0.56860 (14)0.0579 (4)
H20.19161.06610.56010.069*
C30.0896 (3)0.8105 (3)0.62124 (16)0.0655 (4)
H3−0.04070.82760.64800.079*
C40.1445 (3)0.6443 (2)0.63387 (13)0.0594 (4)
C50.0011 (4)0.4859 (3)0.69263 (18)0.0797 (6)
H5C0.04750.37160.67610.096*
H5B−0.14590.46380.66370.096*
H5A0.01050.52180.77550.096*
C60.3403 (3)0.6293 (2)0.58998 (16)0.0641 (4)
H60.37930.51680.59710.077*
C70.0828 (2)0.96057 (19)1.02576 (12)0.0513 (4)
C80.2406 (3)1.0695 (2)1.10747 (14)0.0632 (4)
H80.24421.19581.13150.076*
C90.3905 (3)0.9892 (3)1.15227 (15)0.0679 (5)
H90.49731.06141.20660.082*
C100.3838 (3)0.8018 (2)1.11714 (14)0.0600 (4)
C110.5426 (3)0.7065 (3)1.1636 (2)0.0793 (5)
H11C0.50700.57551.13050.095*
H11B0.53740.71301.24700.095*
H11A0.68560.76991.14310.095*
C120.2214 (3)0.7049 (2)1.03580 (18)0.0686 (5)
H120.21460.57821.01090.082*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0614 (8)0.0537 (7)0.0719 (8)0.0235 (6)0.0113 (6)0.0111 (6)
N20.0615 (8)0.0483 (7)0.0819 (9)0.0103 (6)−0.0066 (7)−0.0034 (6)
C10.0470 (7)0.0513 (7)0.0491 (7)0.0170 (6)−0.0020 (5)0.0031 (5)
C20.0500 (8)0.0626 (9)0.0669 (9)0.0231 (6)0.0037 (6)0.0129 (7)
C30.0508 (8)0.0790 (11)0.0696 (9)0.0200 (8)0.0091 (7)0.0131 (8)
C40.0607 (9)0.0615 (9)0.0513 (7)0.0076 (7)0.0001 (6)0.0067 (6)
C50.0809 (13)0.0784 (12)0.0723 (11)0.0034 (10)0.0095 (9)0.0176 (9)
C60.0734 (10)0.0539 (8)0.0690 (9)0.0212 (7)0.0104 (8)0.0125 (7)
C70.0527 (7)0.0454 (7)0.0523 (7)0.0062 (6)0.0075 (6)0.0052 (5)
C80.0722 (10)0.0521 (8)0.0608 (8)0.0129 (7)−0.0068 (7)−0.0031 (6)
C90.0727 (10)0.0664 (10)0.0595 (9)0.0131 (8)−0.0108 (7)0.0003 (7)
C100.0567 (8)0.0625 (9)0.0620 (8)0.0137 (7)0.0086 (7)0.0158 (7)
C110.0705 (11)0.0809 (13)0.0911 (13)0.0247 (10)−0.0004 (10)0.0194 (10)
C120.0640 (10)0.0500 (8)0.0896 (12)0.0137 (7)−0.0015 (8)0.0017 (8)

Geometric parameters (Å, °)

C1—N11.334 (2)C7—N21.335 (2)
C1—C21.393 (2)C7—C81.389 (2)
C1—C1i1.491 (3)C7—C7ii1.475 (3)
C2—C31.384 (3)C8—C91.368 (3)
C2—H20.9300C8—H80.9300
C3—C41.371 (3)C9—C101.377 (3)
C3—H30.9300C9—H90.9300
C4—C61.389 (3)C10—C121.380 (3)
C4—C51.511 (3)C10—C111.494 (3)
C5—H5C0.9600C11—H11C0.9600
C5—H5B0.9600C11—H11B0.9600
C5—H5A0.9600C11—H11A0.9600
C6—N11.340 (2)C12—N21.327 (2)
C6—H60.9300C12—H120.9300
N1—C1—C2121.57 (15)N2—C7—C7ii116.86 (16)
N1—C1—C1i116.75 (16)C8—C7—C7ii121.84 (17)
C2—C1—C1i121.68 (16)C9—C8—C7119.40 (16)
C3—C2—C1119.51 (15)C9—C8—H8120.3
C3—C2—H2120.2C7—C8—H8120.3
C1—C2—H2120.2C8—C9—C10120.16 (16)
C4—C3—C2119.99 (16)C8—C9—H9119.9
C4—C3—H3120.0C10—C9—H9119.9
C2—C3—H3120.0C9—C10—C12116.32 (17)
C3—C4—C6116.29 (16)C9—C10—C11122.45 (18)
C3—C4—C5122.09 (17)C12—C10—C11121.22 (17)
C6—C4—C5121.62 (17)C10—C11—H11C109.5
C4—C5—H5C109.5C10—C11—H11B109.5
C4—C5—H5B109.5H11C—C11—H11B109.5
H5C—C5—H5B109.5C10—C11—H11A109.5
C4—C5—H5A109.5H11C—C11—H11A109.5
H5C—C5—H5A109.5H11B—C11—H11A109.5
H5B—C5—H5A109.5N2—C12—C10124.98 (16)
N1—C6—C4125.26 (16)N2—C12—H12117.5
N1—C6—H6117.4C10—C12—H12117.5
C4—C6—H6117.4C1—N1—C6117.36 (15)
N2—C7—C8121.30 (15)C12—N2—C7117.84 (15)
N1—C1—C2—C30.7 (2)C8—C9—C10—C120.4 (3)
C1i—C1—C2—C3−179.66 (16)C8—C9—C10—C11−179.67 (17)
C1—C2—C3—C40.3 (3)C9—C10—C12—N2−0.2 (3)
C2—C3—C4—C6−0.9 (3)C11—C10—C12—N2179.92 (17)
C2—C3—C4—C5178.87 (16)C2—C1—N1—C6−0.9 (2)
C3—C4—C6—N10.7 (3)C1i—C1—N1—C6179.44 (15)
C5—C4—C6—N1−179.06 (16)C4—C6—N1—C10.2 (3)
N2—C7—C8—C90.2 (3)C10—C12—N2—C7−0.1 (3)
C7ii—C7—C8—C9−179.88 (17)C8—C7—N2—C120.0 (3)
C7—C8—C9—C10−0.5 (3)C7ii—C7—N2—C12−179.87 (17)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9—H9···Cg1iii0.932.783.669 (3)160

Symmetry codes: (iii) −x+1, −y+2, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2693).

References

  • Ahmadi, R., Khalighi, A., Kalateh, K., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1233. [PMC free article] [PubMed]
  • Albada, G. A., Mohamadou, A., Mutikainen, I., Turpeinen, U. & Reedijk, J. (2004). Eur. J. Inorg. Chem. pp. 3733–3742.
  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Amani, V., Safari, N. & Khavasi, H. R. (2007). Polyhedron, 26, 4257–4262.
  • Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Kalateh, K., Ahmadi, R., Ebadi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1353–m1354. [PMC free article] [PubMed]
  • Khalighi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1211–m1212. [PMC free article] [PubMed]
  • Maheshwari, V., Carlone, M., Fronczek, F. R. & Marzilli, L. G. (2007). Acta Cryst. B63, 603–611. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tadayon Pour, N., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1305. [PMC free article] [PubMed]

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