2,2'-Dimethyl-4,4'-bipyridine.

In the crystal structure of the title compound, C(12)H(12)N(2), the mol-ecule 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 inter-actions, with a distance of 3.81 (1) Å between the ring centroids.

Related literature

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 et al. (2005 ▶); Kryschenko et al. (2003 ▶); Lynch et al. (1999 ▶); Yaghi et al. (1995 ▶).

Experimental

Crystal data

C12H12N2

M = 184.24

Orthorhombic,

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 ▶) 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 ▶); cell refinement: SAINT-NT (Bruker, 2004 ▶); data reduction: SAINT-NT; 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 ▶).

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

C12H12N2	F000 = 784
Mr = 184.24	Dx = 1.280 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5227 reflections
a = 11.7961 (3) Å	θ = 2.6–31.2º
b = 7.6130 (2) Å	µ = 0.08 mm−1
c = 21.2977 (5) Å	T = 153 (2) K
V = 1912.61 (8) Å3	Needle, colourless
Z = 8	0.54 × 0.24 × 0.14 mm

Bruker X8 APEXII CCD area-detector diffractometer	3233 independent reflections
Radiation source: fine-focus sealed tube	2262 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.066
T = 153(2) K	θmax = 31.7º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	h = −17→17
Tmin = 0.924, Tmax = 0.989	k = −10→11
26242 measured reflections	l = −31→28

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-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 reflections	Δρmax = 0.37 e Å−3
129 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
N1	0.83087 (7)	0.16449 (12)	0.48415 (4)	0.0253 (2)
N2	0.38746 (7)	−0.09210 (12)	0.27478 (4)	0.0235 (2)
C1	0.65454 (8)	0.06887 (12)	0.40087 (5)	0.0179 (2)
C2	0.76889 (8)	0.05080 (13)	0.38471 (5)	0.0206 (2)
H2	0.7889	0.0062	0.3446	0.025*
C3	0.85371 (8)	0.09788 (13)	0.42717 (5)	0.0215 (2)
C4	0.72102 (9)	0.18301 (15)	0.49892 (5)	0.0269 (2)
H4	0.7034	0.2310	0.5389	0.032*
C5	0.63117 (8)	0.13748 (14)	0.46021 (5)	0.0230 (2)
H5	0.5551	0.1527	0.4738	0.028*
C6	0.97634 (9)	0.07391 (15)	0.41063 (6)	0.0278 (2)
H6A	1.0152	0.1875	0.4127	0.042*
H6B	0.9825	0.0265	0.3680	0.042*
H6C	1.0115	−0.0079	0.4404	0.042*
C7	0.56279 (8)	0.01492 (12)	0.35706 (5)	0.0175 (2)
C8	0.44859 (8)	0.05087 (13)	0.36967 (5)	0.0194 (2)
H8	0.4285	0.1139	0.4065	0.023*
C9	0.36413 (8)	−0.00544 (13)	0.32832 (5)	0.0206 (2)
C10	0.49692 (8)	−0.12586 (15)	0.26316 (5)	0.0247 (2)
H10	0.5148	−0.1876	0.2257	0.030*
C11	0.58594 (8)	−0.07721 (13)	0.30182 (5)	0.0220 (2)
H11	0.6618	−0.1061	0.2909	0.026*
C12	0.24104 (9)	0.02673 (16)	0.34184 (6)	0.0288 (3)
H12A	0.2111	0.1128	0.3119	0.043*
H12B	0.2327	0.0721	0.3847	0.043*
H12C	0.1990	−0.0837	0.3378	0.043*

	U11	U22	U33	U12	U13	U23
N1	0.0222 (4)	0.0285 (5)	0.0252 (5)	0.0012 (3)	−0.0059 (4)	−0.0026 (3)
N2	0.0210 (4)	0.0277 (5)	0.0218 (5)	−0.0023 (3)	−0.0015 (3)	−0.0032 (3)
C1	0.0165 (4)	0.0192 (4)	0.0179 (5)	−0.0005 (3)	−0.0014 (3)	0.0009 (3)
C2	0.0178 (4)	0.0245 (5)	0.0196 (5)	−0.0002 (3)	−0.0006 (4)	−0.0001 (3)
C3	0.0185 (4)	0.0220 (5)	0.0241 (5)	−0.0006 (3)	−0.0034 (4)	0.0030 (4)
C4	0.0250 (5)	0.0343 (6)	0.0214 (5)	0.0027 (4)	−0.0038 (4)	−0.0068 (4)
C5	0.0198 (4)	0.0290 (5)	0.0201 (5)	0.0010 (4)	−0.0012 (4)	−0.0027 (4)
C6	0.0173 (5)	0.0353 (6)	0.0310 (6)	0.0003 (4)	−0.0031 (4)	0.0008 (4)
C7	0.0164 (4)	0.0191 (4)	0.0170 (5)	−0.0013 (3)	−0.0009 (3)	0.0021 (3)
C8	0.0172 (4)	0.0221 (5)	0.0189 (5)	0.0002 (3)	−0.0005 (3)	−0.0017 (3)
C9	0.0173 (4)	0.0230 (5)	0.0214 (5)	−0.0002 (3)	−0.0018 (4)	0.0001 (4)
C10	0.0230 (5)	0.0313 (5)	0.0197 (5)	−0.0019 (4)	0.0011 (4)	−0.0053 (4)
C11	0.0182 (4)	0.0281 (5)	0.0196 (5)	−0.0006 (3)	0.0012 (4)	−0.0025 (4)
C12	0.0176 (5)	0.0371 (6)	0.0316 (6)	0.0027 (4)	−0.0023 (4)	−0.0076 (5)

N1—C4	1.3408 (13)	C6—H6B	0.9800
N1—C3	1.3426 (14)	C6—H6C	0.9800
N2—C10	1.3395 (13)	C7—C11	1.3967 (14)
N2—C9	1.3459 (13)	C7—C8	1.4006 (13)
C1—C5	1.3949 (14)	C8—C9	1.3971 (14)
C1—C2	1.3989 (13)	C8—H8	0.9500
C1—C7	1.4868 (13)	C9—C12	1.5004 (13)
C2—C3	1.3955 (14)	C10—C11	1.3848 (14)
C2—H2	0.9500	C10—H10	0.9500
C3—C6	1.5000 (14)	C11—H11	0.9500
C4—C5	1.3869 (14)	C12—H12A	0.9800
C4—H4	0.9500	C12—H12B	0.9800
C5—H5	0.9500	C12—H12C	0.9800
C6—H6A	0.9800
C4—N1—C3	116.47 (9)	H6B—C6—H6C	109.5
C10—N2—C9	116.59 (9)	C11—C7—C8	116.59 (9)
C5—C1—C2	116.77 (9)	C11—C7—C1	121.67 (9)
C5—C1—C7	121.88 (9)	C8—C7—C1	121.73 (9)
C2—C1—C7	121.35 (9)	C9—C8—C7	120.34 (9)
C3—C2—C1	120.44 (10)	C9—C8—H8	119.8
C3—C2—H2	119.8	C7—C8—H8	119.8
C1—C2—H2	119.8	N2—C9—C8	122.59 (9)
N1—C3—C2	122.61 (9)	N2—C9—C12	116.14 (9)
N1—C3—C6	116.85 (9)	C8—C9—C12	121.27 (9)
C2—C3—C6	120.53 (10)	N2—C10—C11	124.74 (10)
N1—C4—C5	124.94 (10)	N2—C10—H10	117.6
N1—C4—H4	117.5	C11—C10—H10	117.6
C5—C4—H4	117.5	C10—C11—C7	119.13 (9)
C4—C5—C1	118.76 (10)	C10—C11—H11	120.4
C4—C5—H5	120.6	C7—C11—H11	120.4
C1—C5—H5	120.6	C9—C12—H12A	109.5
C3—C6—H6A	109.5	C9—C12—H12B	109.5
C3—C6—H6B	109.5	H12A—C12—H12B	109.5
H6A—C6—H6B	109.5	C9—C12—H12C	109.5
C3—C6—H6C	109.5	H12A—C12—H12C	109.5
H6A—C6—H6C	109.5	H12B—C12—H12C	109.5
C5—C1—C2—C3	0.87 (14)	C5—C1—C7—C8	8.36 (15)
C7—C1—C2—C3	−178.28 (9)	C2—C1—C7—C8	−172.52 (9)
C4—N1—C3—C2	0.45 (15)	C11—C7—C8—C9	0.41 (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—C8	1.31 (15)
C1—C2—C3—C6	178.28 (9)	C10—N2—C9—C12	−178.16 (9)
C3—N1—C4—C5	0.55 (16)	C7—C8—C9—N2	−1.35 (15)
N1—C4—C5—C1	−0.80 (17)	C7—C8—C9—C12	178.10 (9)
C2—C1—C5—C4	0.05 (15)	C9—N2—C10—C11	−0.42 (17)
C7—C1—C5—C4	179.20 (9)	N2—C10—C11—C7	−0.46 (17)
C5—C1—C7—C11	−170.38 (9)	C8—C7—C11—C10	0.43 (14)
C2—C1—C7—C11	8.74 (14)	C1—C7—C11—C10	179.24 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6C···N1i	0.98	2.73	3.6728 (16)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6C⋯N1i	0.98	2.73	3.6728 (16)	161

Symmetry code: (i) .