2,2',6,6'-Tetra-methyl-4,4'-bipyridine.

In the title compound, C(14)H(16)N(2), which has no crystallographic molecular symmetry, the dihedral angle between the least-squares planes of the two pyridine rings is 19.48 (2)°. No classical hydrogen bonds nor π-π inter-actions were found.

Related literature

For the synthesis of the title compound, see: Hunig & Wehner (1989 ▶). For related compounds, see: Coles et al. (2002 ▶); Jackisch et al. (1990 ▶); Lin et al. (2006 ▶).

Experimental

Crystal data

C14H16N2

M = 212.29

Tetragonal,

a = 21.9827 (10) Å

c = 10.1569 (6) Å

V = 4908.2 (4) Å3

Z = 16

Mo Kα radiation

μ = 0.07 mm−1

T = 293 (2) K

0.32 × 0.26 × 0.26 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.979, T max = 0.982

14604 measured reflections

2959 independent reflections

2112 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.165

S = 1.06

2959 reflections

149 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063040/om2191sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063040/om2191Isup2.hkl

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

C14H16N2	Z = 16
Mr = 212.29	F000 = 1824
Tetragonal, I41/a	Dx = 1.149 Mg m−3
a = 21.9827 (10) Å	Mo Kα radiation λ = 0.71073 Å
b = 21.9827 (10) Å	Cell parameters from 352 reflections
c = 10.1569 (6) Å	θ = 2.6–24.8º
α = 90º	µ = 0.07 mm−1
β = 90º	T = 293 (2) K
γ = 90º	Block, yellow
V = 4908.2 (4) Å3	0.32 × 0.26 × 0.26 mm

Bruker SMART APEXII diffractometer	2959 independent reflections
Radiation source: fine-focus sealed tube	2112 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 293(2) K	θmax = 28.3º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2004)	h = −28→28
Tmin = 0.979, Tmax = 0.982	k = −21→29
14604 measured reflections	l = −12→13

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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.165	w = 1/[σ2(Fo2) + (0.0889P)2 + 1.2656P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.002
2959 reflections	Δρmax = 0.22 e Å−3
149 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.36926 (6)	0.13022 (6)	−0.07996 (14)	0.0547 (4)
N2	0.14766 (6)	0.34910 (6)	0.10403 (13)	0.0501 (3)
C1	0.33348 (7)	0.12075 (7)	0.02437 (16)	0.0486 (4)
C2	0.28970 (6)	0.16252 (6)	0.06394 (15)	0.0442 (3)
H2	0.2659	0.1545	0.1377	0.053*
C3	0.28130 (6)	0.21610 (6)	−0.00610 (14)	0.0415 (3)
C4	0.31887 (7)	0.22525 (7)	−0.11452 (16)	0.0509 (4)
H4	0.3149	0.2604	−0.1649	0.061*
C5	0.36228 (7)	0.18207 (8)	−0.14767 (16)	0.0551 (4)
C6	0.14380 (6)	0.29160 (7)	0.14839 (15)	0.0453 (4)
C7	0.18561 (6)	0.24730 (7)	0.11270 (15)	0.0449 (4)
H7	0.1805	0.2075	0.1420	0.054*
C8	0.23495 (6)	0.26192 (6)	0.03364 (14)	0.0411 (3)
C9	0.23940 (7)	0.32206 (6)	−0.00853 (16)	0.0483 (4)
H9	0.2722	0.3343	−0.0600	0.058*
C10	0.19490 (7)	0.36346 (6)	0.02641 (16)	0.0504 (4)
C11	0.34380 (10)	0.06300 (8)	0.1000 (2)	0.0704 (5)
H11A	0.3147	0.0330	0.0727	0.106*
H11B	0.3391	0.0708	0.1924	0.106*
H11C	0.3842	0.0483	0.0832	0.106*
C12	0.40499 (10)	0.19262 (11)	−0.2612 (2)	0.0815 (6)
H12A	0.4440	0.2051	−0.2282	0.122*
H12B	0.3888	0.2238	−0.3173	0.122*
H12C	0.4094	0.1556	−0.3106	0.122*
C13	0.09245 (7)	0.27763 (9)	0.24106 (17)	0.0588 (4)
H13A	0.1058	0.2836	0.3301	0.088*
H13B	0.0799	0.2361	0.2295	0.088*
H13C	0.0588	0.3042	0.2228	0.088*
C14	0.19686 (10)	0.42776 (8)	−0.0243 (2)	0.0759 (6)
H14A	0.1633	0.4344	−0.0832	0.114*
H14B	0.2344	0.4344	−0.0703	0.114*
H14C	0.1940	0.4556	0.0484	0.114*

	U11	U22	U33	U12	U13	U23
N1	0.0522 (7)	0.0543 (8)	0.0574 (8)	0.0114 (6)	0.0035 (6)	−0.0052 (6)
N2	0.0475 (7)	0.0470 (7)	0.0558 (8)	0.0060 (5)	0.0012 (6)	−0.0011 (6)
C1	0.0492 (8)	0.0439 (8)	0.0527 (9)	0.0059 (6)	−0.0042 (7)	−0.0017 (6)
C2	0.0426 (7)	0.0413 (7)	0.0487 (8)	0.0012 (6)	0.0013 (6)	0.0010 (6)
C3	0.0363 (7)	0.0388 (7)	0.0495 (8)	−0.0006 (5)	−0.0014 (6)	−0.0011 (6)
C4	0.0512 (8)	0.0480 (8)	0.0537 (9)	0.0045 (6)	0.0070 (7)	0.0061 (7)
C5	0.0518 (9)	0.0597 (10)	0.0539 (9)	0.0059 (7)	0.0080 (7)	−0.0024 (7)
C6	0.0385 (7)	0.0505 (8)	0.0469 (8)	0.0001 (6)	−0.0023 (6)	−0.0008 (6)
C7	0.0427 (7)	0.0400 (7)	0.0519 (8)	−0.0006 (6)	0.0013 (6)	0.0047 (6)
C8	0.0384 (7)	0.0380 (7)	0.0470 (8)	0.0010 (5)	−0.0017 (6)	0.0004 (6)
C9	0.0446 (8)	0.0423 (8)	0.0579 (9)	0.0005 (6)	0.0063 (7)	0.0056 (6)
C10	0.0503 (8)	0.0403 (8)	0.0606 (9)	0.0038 (6)	0.0010 (7)	0.0022 (7)
C11	0.0815 (13)	0.0534 (10)	0.0764 (13)	0.0223 (9)	0.0073 (10)	0.0065 (9)
C12	0.0752 (13)	0.0951 (15)	0.0743 (13)	0.0159 (11)	0.0300 (10)	0.0069 (11)
C13	0.0466 (9)	0.0706 (11)	0.0590 (10)	0.0001 (7)	0.0070 (7)	0.0017 (8)
C14	0.0772 (13)	0.0447 (9)	0.1057 (16)	0.0116 (8)	0.0158 (11)	0.0139 (9)

N1—C1	1.336 (2)	C8—C9	1.3931 (19)
N1—C5	1.340 (2)	C9—C10	1.383 (2)
N2—C10	1.341 (2)	C9—H9	0.9300
N2—C6	1.3446 (19)	C10—C14	1.505 (2)
C1—C2	1.389 (2)	C11—H11A	0.9600
C1—C11	1.501 (2)	C11—H11B	0.9600
C2—C3	1.3885 (19)	C11—H11C	0.9600
C2—H2	0.9300	C12—H12A	0.9600
C3—C4	1.391 (2)	C12—H12B	0.9600
C3—C8	1.4886 (19)	C12—H12C	0.9600
C4—C5	1.388 (2)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C12	1.505 (2)	C13—H13C	0.9600
C6—C7	1.387 (2)	C14—H14A	0.9600
C6—C13	1.502 (2)	C14—H14B	0.9600
C7—C8	1.3873 (19)	C14—H14C	0.9600
C7—H7	0.9300
C1—N1—C5	118.18 (13)	C8—C9—H9	120.1
C10—N2—C6	117.84 (12)	N2—C10—C9	122.93 (13)
N1—C1—C2	122.29 (14)	N2—C10—C14	116.37 (14)
N1—C1—C11	116.65 (14)	C9—C10—C14	120.69 (15)
C2—C1—C11	121.04 (15)	C1—C11—H11A	109.5
C3—C2—C1	120.29 (14)	C1—C11—H11B	109.5
C3—C2—H2	119.9	H11A—C11—H11B	109.5
C1—C2—H2	119.9	C1—C11—H11C	109.5
C2—C3—C4	116.71 (13)	H11A—C11—H11C	109.5
C2—C3—C8	121.74 (13)	H11B—C11—H11C	109.5
C4—C3—C8	121.55 (13)	C5—C12—H12A	109.5
C5—C4—C3	120.10 (14)	C5—C12—H12B	109.5
C5—C4—H4	120.0	H12A—C12—H12B	109.5
C3—C4—H4	120.0	C5—C12—H12C	109.5
N1—C5—C4	122.42 (15)	H12A—C12—H12C	109.5
N1—C5—C12	116.94 (15)	H12B—C12—H12C	109.5
C4—C5—C12	120.63 (16)	C6—C13—H13A	109.5
N2—C6—C7	122.05 (13)	C6—C13—H13B	109.5
N2—C6—C13	116.73 (13)	H13A—C13—H13B	109.5
C7—C6—C13	121.21 (14)	C6—C13—H13C	109.5
C6—C7—C8	120.44 (13)	H13A—C13—H13C	109.5
C6—C7—H7	119.8	H13B—C13—H13C	109.5
C8—C7—H7	119.8	C10—C14—H14A	109.5
C7—C8—C9	116.92 (13)	C10—C14—H14B	109.5
C7—C8—C3	122.38 (12)	H14A—C14—H14B	109.5
C9—C8—C3	120.70 (13)	C10—C14—H14C	109.5
C10—C9—C8	119.74 (13)	H14A—C14—H14C	109.5
C10—C9—H9	120.1	H14B—C14—H14C	109.5
C5—N1—C1—C2	0.2 (2)	N2—C6—C7—C8	2.9 (2)
C5—N1—C1—C11	−178.33 (16)	C13—C6—C7—C8	−175.91 (14)
N1—C1—C2—C3	0.7 (2)	C6—C7—C8—C9	−1.0 (2)
C11—C1—C2—C3	179.13 (15)	C6—C7—C8—C3	179.37 (13)
C1—C2—C3—C4	−0.6 (2)	C2—C3—C8—C7	−20.9 (2)
C1—C2—C3—C8	−179.86 (13)	C4—C3—C8—C7	159.85 (14)
C2—C3—C4—C5	−0.3 (2)	C2—C3—C8—C9	159.45 (14)
C8—C3—C4—C5	178.97 (14)	C4—C3—C8—C9	−19.8 (2)
C1—N1—C5—C4	−1.1 (2)	C7—C8—C9—C10	−1.5 (2)
C1—N1—C5—C12	177.52 (16)	C3—C8—C9—C10	178.14 (14)
C3—C4—C5—N1	1.2 (3)	C6—N2—C10—C9	−0.4 (2)
C3—C4—C5—C12	−177.38 (16)	C6—N2—C10—C14	178.45 (16)
C10—N2—C6—C7	−2.2 (2)	C8—C9—C10—N2	2.3 (3)
C10—N2—C6—C13	176.71 (14)	C8—C9—C10—C14	−176.52 (16)

Table 1

Selected torsion angles (°)

C2—C3—C8—C7	−20.9 (2)
C4—C3—C8—C7	159.85 (14)
C2—C3—C8—C9	159.45 (14)
C4—C3—C8—C9	−19.8 (2)