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

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5,5′-Di­methyl-2,2′-bi­pyridine

aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran, bDepartment of Chemistry, Islamic Azad University, Kazerun Branch, Kazerun, Fars, Iran, and cDamghan University of Basic Sciences, School of Chemistry, Damghan, Iran
*Correspondence e-mail: alizadeh@dubs.ac.ir

(Received 19 May 2009; accepted 20 May 2009; online 17 June 2009)

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 ππ 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[Ahmadi, R., Khalighi, A., Kalateh, K., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1233.]); Albada et al. (2004[Albada, G. A., Mohamadou, A., Mutikainen, I., Turpeinen, U. & Reedijk, J. (2004). Eur. J. Inorg. Chem. pp. 3733-3742.]); Amani et al. (2007[Amani, V., Safari, N. & Khavasi, H. R. (2007). Polyhedron, 26, 4257-4262.]); Kalateh et al. (2008[Kalateh, K., Ahmadi, R., Ebadi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1353-m1354.]); Khalighi et al. (2008[Khalighi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1211-m1212.]); Maheshwari et al. (2007[Maheshwari, V., Carlone, M., Fronczek, F. R. & Marzilli, L. G. (2007). Acta Cryst. B63, 603-611.]); Tadayon Pour et al. (2008[Tadayon Pour, N., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1305.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12N2

  • Mr = 184.24

  • Triclinic, [P \overline 1]

  • 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)

  • Rint = 0.082

Refinement
  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C9—H9⋯Cg1i 0.93 2.78 3.669 (3) 160
Symmetry code: (i) -x+1, -y+2, -z+2. Cg1 is the centroid of the N1,C1–C4,C6 ring.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

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 ππ 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).

Related literature top

For related structures, see: Ahmadi et al. (2008); Albada et al. (2004); Amani et al. (2007); Kalateh et al. (2008); Khalighi et al. (2008); Maheshwari et al. (2007); Tadayon Pour et al. (2008). For bond-length data, see: Allen et al. (1987). Cg1 is the centroid of the N1,C1–C4,C6 ring.

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] 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].
[Figure 2] Fig. 2. A partial packing diagram of the title compound.
5,5'-Dimethyl-2,2'-bipyridine top
Crystal data top
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 top
Bruker SMART CCD area-detector
diffractometer
2067 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.082
Graphite monochromatorθmax = 29.3°, θmin = 1.8°
ϕ and ω scansh = 88
6191 measured reflectionsk = 1010
2739 independent reflectionsl = 1515
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205H-atom parameters constrained
S = 1.08 w = 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
Crystal data top
C12H12N2γ = 105.03 (5)°
Mr = 184.24V = 518.4 (6) Å3
Triclinic, P1Z = 2
a = 6.409 (4) ÅMo Kα radiation
b = 7.312 (5) ŵ = 0.07 mm1
c = 11.533 (8) ÅT = 298 K
α = 96.04 (5)°0.50 × 0.41 × 0.29 mm
β = 91.16 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2067 reflections with I > 2σ(I)
6191 measured reflectionsRint = 0.082
2739 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.205H-atom parameters constrained
S = 1.08Δρmax = 0.27 e Å3
2739 reflectionsΔρmin = 0.24 e Å3
129 parameters
Special details top

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) top
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)
H30.04070.82760.64800.079*
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*
H5B0.14590.46380.66370.096*
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) top
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, º) top
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—C3179.66 (16)C8—C9—C10—C11179.67 (17)
C1—C2—C3—C40.3 (3)C9—C10—C12—N20.2 (3)
C2—C3—C4—C60.9 (3)C11—C10—C12—N2179.92 (17)
C2—C3—C4—C5178.87 (16)C2—C1—N1—C60.9 (2)
C3—C4—C6—N10.7 (3)C1i—C1—N1—C6179.44 (15)
C5—C4—C6—N1179.06 (16)C4—C6—N1—C10.2 (3)
N2—C7—C8—C90.2 (3)C10—C12—N2—C70.1 (3)
C7ii—C7—C8—C9179.88 (17)C8—C7—N2—C120.0 (3)
C7—C8—C9—C100.5 (3)C7ii—C7—N2—C12179.87 (17)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···Cg1iii0.932.783.669 (3)160
Symmetry code: (iii) x+1, y+2, z+2.

Experimental details

Crystal data
Chemical formulaC12H12N2
Mr184.24
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)6.409 (4), 7.312 (5), 11.533 (8)
α, β, γ (°)96.04 (5), 91.16 (4), 105.03 (5)
V3)518.4 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.50 × 0.41 × 0.29
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6191, 2739, 2067
Rint0.082
(sin θ/λ)max1)0.688
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.205, 1.08
No. of reflections2739
No. of parameters129
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.24

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···Cg1i0.932.783.669 (3)160
Symmetry code: (i) x+1, y+2, z+2.
 

Acknowledgements

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

References

First citationAhmadi, R., Khalighi, A., Kalateh, K., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1233.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAlbada, G. A., Mohamadou, A., Mutikainen, I., Turpeinen, U. & Reedijk, J. (2004). Eur. J. Inorg. Chem. pp. 3733–3742.  Google Scholar
First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
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First citationKhalighi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1211–m1212.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationMaheshwari, V., Carlone, M., Fronczek, F. R. & Marzilli, L. G. (2007). Acta Cryst. B63, 603–611.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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First citationTadayon Pour, N., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1305.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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