5,5'-Dimethyl-2,2'-bipyridine.

The asymmetric unit of the title compound, C(12)H(12)N(2), contains two half-mol-ecules 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 inter-action is also found.

Related literature

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 ▶).

Experimental

Crystal data

C12H12N2

M = 184.24

Triclinic,

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

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

C12H12N2	Z = 2
Mr = 184.24	F(000) = 196
Triclinic, P1	Dx = 1.180 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.409 (4) Å	Cell parameters from 1133 reflections
b = 7.312 (5) Å	θ = 1.8–29.3°
c = 11.533 (8) Å	µ = 0.07 mm−1
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

Bruker SMART CCD area-detector diffractometer	2067 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.082
graphite	θmax = 29.3°, θmin = 1.8°
φ and ω scans	h = −8→8
6191 measured reflections	k = −10→10
2739 independent reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205	H-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 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.4778 (2)	0.76393 (19)	0.53822 (13)	0.0604 (4)
N2	0.0741 (2)	0.77876 (19)	0.99037 (14)	0.0656 (4)
C1	0.4223 (2)	0.92544 (19)	0.52837 (12)	0.0486 (3)
C2	0.2280 (2)	0.9529 (2)	0.56860 (14)	0.0579 (4)
H2	0.1916	1.0661	0.5601	0.069*
C3	0.0896 (3)	0.8105 (3)	0.62124 (16)	0.0655 (4)
H3	−0.0407	0.8276	0.6480	0.079*
C4	0.1445 (3)	0.6443 (2)	0.63387 (13)	0.0594 (4)
C5	0.0011 (4)	0.4859 (3)	0.69263 (18)	0.0797 (6)
H5C	0.0475	0.3716	0.6761	0.096*
H5B	−0.1459	0.4638	0.6637	0.096*
H5A	0.0105	0.5218	0.7755	0.096*
C6	0.3403 (3)	0.6293 (2)	0.58998 (16)	0.0641 (4)
H6	0.3793	0.5168	0.5971	0.077*
C7	0.0828 (2)	0.96057 (19)	1.02576 (12)	0.0513 (4)
C8	0.2406 (3)	1.0695 (2)	1.10747 (14)	0.0632 (4)
H8	0.2442	1.1958	1.1315	0.076*
C9	0.3905 (3)	0.9892 (3)	1.15227 (15)	0.0679 (5)
H9	0.4973	1.0614	1.2066	0.082*
C10	0.3838 (3)	0.8018 (2)	1.11714 (14)	0.0600 (4)
C11	0.5426 (3)	0.7065 (3)	1.1636 (2)	0.0793 (5)
H11C	0.5070	0.5755	1.1305	0.095*
H11B	0.5374	0.7130	1.2470	0.095*
H11A	0.6856	0.7699	1.1431	0.095*
C12	0.2214 (3)	0.7049 (2)	1.03580 (18)	0.0686 (5)
H12	0.2146	0.5782	1.0109	0.082*

	U11	U22	U33	U12	U13	U23
N1	0.0614 (8)	0.0537 (7)	0.0719 (8)	0.0235 (6)	0.0113 (6)	0.0111 (6)
N2	0.0615 (8)	0.0483 (7)	0.0819 (9)	0.0103 (6)	−0.0066 (7)	−0.0034 (6)
C1	0.0470 (7)	0.0513 (7)	0.0491 (7)	0.0170 (6)	−0.0020 (5)	0.0031 (5)
C2	0.0500 (8)	0.0626 (9)	0.0669 (9)	0.0231 (6)	0.0037 (6)	0.0129 (7)
C3	0.0508 (8)	0.0790 (11)	0.0696 (9)	0.0200 (8)	0.0091 (7)	0.0131 (8)
C4	0.0607 (9)	0.0615 (9)	0.0513 (7)	0.0076 (7)	0.0001 (6)	0.0067 (6)
C5	0.0809 (13)	0.0784 (12)	0.0723 (11)	0.0034 (10)	0.0095 (9)	0.0176 (9)
C6	0.0734 (10)	0.0539 (8)	0.0690 (9)	0.0212 (7)	0.0104 (8)	0.0125 (7)
C7	0.0527 (7)	0.0454 (7)	0.0523 (7)	0.0062 (6)	0.0075 (6)	0.0052 (5)
C8	0.0722 (10)	0.0521 (8)	0.0608 (8)	0.0129 (7)	−0.0068 (7)	−0.0031 (6)
C9	0.0727 (10)	0.0664 (10)	0.0595 (9)	0.0131 (8)	−0.0108 (7)	0.0003 (7)
C10	0.0567 (8)	0.0625 (9)	0.0620 (8)	0.0137 (7)	0.0086 (7)	0.0158 (7)
C11	0.0705 (11)	0.0809 (13)	0.0911 (13)	0.0247 (10)	−0.0004 (10)	0.0194 (10)
C12	0.0640 (10)	0.0500 (8)	0.0896 (12)	0.0137 (7)	−0.0015 (8)	0.0017 (8)

C1—N1	1.334 (2)	C7—N2	1.335 (2)
C1—C2	1.393 (2)	C7—C8	1.389 (2)
C1—C1i	1.491 (3)	C7—C7ii	1.475 (3)
C2—C3	1.384 (3)	C8—C9	1.368 (3)
C2—H2	0.9300	C8—H8	0.9300
C3—C4	1.371 (3)	C9—C10	1.377 (3)
C3—H3	0.9300	C9—H9	0.9300
C4—C6	1.389 (3)	C10—C12	1.380 (3)
C4—C5	1.511 (3)	C10—C11	1.494 (3)
C5—H5C	0.9600	C11—H11C	0.9600
C5—H5B	0.9600	C11—H11B	0.9600
C5—H5A	0.9600	C11—H11A	0.9600
C6—N1	1.340 (2)	C12—N2	1.327 (2)
C6—H6	0.9300	C12—H12	0.9300
N1—C1—C2	121.57 (15)	N2—C7—C7ii	116.86 (16)
N1—C1—C1i	116.75 (16)	C8—C7—C7ii	121.84 (17)
C2—C1—C1i	121.68 (16)	C9—C8—C7	119.40 (16)
C3—C2—C1	119.51 (15)	C9—C8—H8	120.3
C3—C2—H2	120.2	C7—C8—H8	120.3
C1—C2—H2	120.2	C8—C9—C10	120.16 (16)
C4—C3—C2	119.99 (16)	C8—C9—H9	119.9
C4—C3—H3	120.0	C10—C9—H9	119.9
C2—C3—H3	120.0	C9—C10—C12	116.32 (17)
C3—C4—C6	116.29 (16)	C9—C10—C11	122.45 (18)
C3—C4—C5	122.09 (17)	C12—C10—C11	121.22 (17)
C6—C4—C5	121.62 (17)	C10—C11—H11C	109.5
C4—C5—H5C	109.5	C10—C11—H11B	109.5
C4—C5—H5B	109.5	H11C—C11—H11B	109.5
H5C—C5—H5B	109.5	C10—C11—H11A	109.5
C4—C5—H5A	109.5	H11C—C11—H11A	109.5
H5C—C5—H5A	109.5	H11B—C11—H11A	109.5
H5B—C5—H5A	109.5	N2—C12—C10	124.98 (16)
N1—C6—C4	125.26 (16)	N2—C12—H12	117.5
N1—C6—H6	117.4	C10—C12—H12	117.5
C4—C6—H6	117.4	C1—N1—C6	117.36 (15)
N2—C7—C8	121.30 (15)	C12—N2—C7	117.84 (15)
N1—C1—C2—C3	0.7 (2)	C8—C9—C10—C12	0.4 (3)
C1i—C1—C2—C3	−179.66 (16)	C8—C9—C10—C11	−179.67 (17)
C1—C2—C3—C4	0.3 (3)	C9—C10—C12—N2	−0.2 (3)
C2—C3—C4—C6	−0.9 (3)	C11—C10—C12—N2	179.92 (17)
C2—C3—C4—C5	178.87 (16)	C2—C1—N1—C6	−0.9 (2)
C3—C4—C6—N1	0.7 (3)	C1i—C1—N1—C6	179.44 (15)
C5—C4—C6—N1	−179.06 (16)	C4—C6—N1—C1	0.2 (3)
N2—C7—C8—C9	0.2 (3)	C10—C12—N2—C7	−0.1 (3)
C7ii—C7—C8—C9	−179.88 (17)	C8—C7—N2—C12	0.0 (3)
C7—C8—C9—C10	−0.5 (3)	C7ii—C7—N2—C12	−179.87 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg1iii	0.93	2.78	3.669 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg1i	0.93	2.78	3.669 (3)	160

Symmetry code: (i) . Cg1 is the centroid of the N1,C1–C4,C6 ring.