4,4'-Di-tert-butyl-2,2'-bipyridine.

In the title compound, C(18)H(24)N(2), the mol-ecular unit adopts a trans conformation around the central C-C bond [N-C-C-N torsion angle of 179.2 (3)°], with the two aromatic rings almost coplanar [dihedral angle of only 0.70 (4)°]. The crystal packing is driven by co-operative contacts involving weak C-H⋯N and C-H⋯π inter-actions, and also the need to fill effectively the available space.

Related literature

For related structures, see: Batsanov et al. (2007 ▶); Coelho et al. (2007 ▶); Paz & Klinowski (2003 ▶); Paz et al. (2002 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C18H24N2

M = 268.39

Monoclinic,

a = 10.241 (5) Å

b = 6.228 (3) Å

c = 24.559 (10) Å

β = 99.75 (3)°

V = 1543.7 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.20 × 0.16 × 0.14 mm

Data collection

Bruker X8 Kappa CCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.98, T max = 0.99

15295 measured reflections

2722 independent reflections

1805 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.217

S = 1.12

2722 reflections

187 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029109/bg2282sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029109/bg2282Isup2.hkl

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

Enhanced figure: interactive version of Fig. 3

Enhanced figure: interactive version of Fig. 4

C18H24N2	F(000) = 584
Mr = 268.39	Dx = 1.155 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5252 reflections
a = 10.241 (5) Å	θ = 3.4–25.3°
b = 6.228 (3) Å	µ = 0.07 mm−1
c = 24.559 (10) Å	T = 296 K
β = 99.75 (3)°	Plate, colourless
V = 1543.7 (12) Å3	0.20 × 0.16 × 0.14 mm
Z = 4

Bruker X8 Kappa CCD APEXII diffractometer	2722 independent reflections
Radiation source: fine-focus sealed tube	1805 reflections with I > 2σ(I)
graphite	Rint = 0.044
ω and φ scans	θmax = 25.3°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −12→11
Tmin = 0.98, Tmax = 0.99	k = −7→5
15295 measured reflections	l = −29→29

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0449P)2 + 4.7425P] where P = (Fo2 + 2Fc2)/3
2722 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.44 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	0.3249 (3)	0.3001 (5)	0.25918 (12)	0.0246 (7)
N2	0.1719 (3)	0.8151 (5)	0.24419 (12)	0.0243 (7)
C1	0.3931 (3)	0.1715 (6)	0.23049 (14)	0.0252 (8)
H1	0.4201	0.0386	0.2456	0.030*
C2	0.4260 (3)	0.2236 (6)	0.17986 (14)	0.0256 (9)
H2	0.4757	0.1284	0.1625	0.031*
C3	0.3852 (3)	0.4166 (6)	0.15491 (13)	0.0227 (8)
C4	0.3118 (3)	0.5477 (6)	0.18389 (14)	0.0240 (8)
H4	0.2801	0.6786	0.1689	0.029*
C5	0.2852 (3)	0.4848 (6)	0.23540 (14)	0.0218 (8)
C6	0.2103 (3)	0.6285 (6)	0.26780 (14)	0.0213 (8)
C7	0.1830 (3)	0.5671 (6)	0.31914 (14)	0.0226 (8)
H7	0.2130	0.4351	0.3340	0.027*
C8	0.1115 (3)	0.7010 (6)	0.34851 (14)	0.0233 (8)
C9	0.0721 (3)	0.8944 (6)	0.32347 (14)	0.0259 (9)
H9	0.0241	0.9917	0.3409	0.031*
C10	0.1041 (3)	0.9434 (6)	0.27250 (15)	0.0258 (9)
H10	0.0763	1.0752	0.2569	0.031*
C11	0.4250 (4)	0.4806 (7)	0.10003 (14)	0.0272 (9)
C12	0.5727 (4)	0.5224 (11)	0.11030 (19)	0.0645 (17)
H12A	0.6188	0.3938	0.1238	0.097*
H12B	0.5929	0.6345	0.1372	0.097*
H12C	0.6000	0.5655	0.0764	0.097*
C13	0.3929 (6)	0.3050 (10)	0.05788 (19)	0.0722 (19)
H13A	0.4108	0.3540	0.0228	0.108*
H13B	0.3009	0.2675	0.0545	0.108*
H13C	0.4464	0.1813	0.0694	0.108*
C14	0.3543 (6)	0.6789 (11)	0.0762 (2)	0.075 (2)
H14A	0.3818	0.7133	0.0417	0.112*
H14B	0.3754	0.7963	0.1015	0.112*
H14C	0.2604	0.6542	0.0701	0.112*
C15	0.0734 (4)	0.6350 (7)	0.40367 (14)	0.0277 (9)
C16	0.1739 (5)	0.4837 (10)	0.43529 (18)	0.0592 (16)
H16A	0.1497	0.4522	0.4705	0.089*
H16B	0.2599	0.5496	0.4407	0.089*
H16C	0.1761	0.3530	0.4147	0.089*
C17	−0.0606 (5)	0.5247 (10)	0.39153 (18)	0.0558 (15)
H17A	−0.1247	0.6214	0.3717	0.084*
H17B	−0.0877	0.4840	0.4256	0.084*
H17C	−0.0541	0.3989	0.3695	0.084*
C18	0.0621 (6)	0.8287 (9)	0.44040 (18)	0.0594 (15)
H18A	−0.0077	0.9208	0.4229	0.089*
H18B	0.1443	0.9062	0.4462	0.089*
H18C	0.0426	0.7812	0.4753	0.089*

	U11	U22	U33	U12	U13	U23
N1	0.0221 (16)	0.0236 (19)	0.0285 (16)	−0.0027 (14)	0.0056 (12)	−0.0015 (13)
N2	0.0191 (15)	0.0244 (19)	0.0306 (16)	0.0026 (14)	0.0073 (12)	0.0036 (14)
C1	0.0225 (19)	0.021 (2)	0.0313 (19)	0.0014 (16)	0.0021 (15)	0.0012 (16)
C2	0.0210 (19)	0.029 (2)	0.0274 (18)	−0.0026 (17)	0.0044 (15)	−0.0060 (16)
C3	0.0175 (18)	0.027 (2)	0.0240 (18)	−0.0001 (16)	0.0029 (14)	−0.0027 (16)
C4	0.0197 (18)	0.026 (2)	0.0256 (18)	0.0016 (16)	0.0027 (14)	0.0020 (16)
C5	0.0166 (17)	0.023 (2)	0.0249 (17)	0.0002 (16)	0.0023 (14)	−0.0001 (15)
C6	0.0165 (17)	0.021 (2)	0.0256 (18)	−0.0033 (15)	0.0013 (14)	−0.0043 (15)
C7	0.0215 (18)	0.019 (2)	0.0260 (18)	0.0003 (16)	0.0015 (14)	0.0009 (15)
C8	0.0178 (18)	0.026 (2)	0.0263 (18)	−0.0042 (16)	0.0031 (14)	−0.0051 (16)
C9	0.0205 (19)	0.026 (2)	0.0320 (19)	0.0022 (16)	0.0064 (15)	−0.0027 (16)
C10	0.0198 (18)	0.024 (2)	0.0336 (19)	0.0025 (16)	0.0055 (15)	0.0023 (17)
C11	0.026 (2)	0.033 (2)	0.0240 (18)	−0.0017 (17)	0.0078 (15)	0.0013 (16)
C12	0.041 (3)	0.112 (5)	0.043 (3)	−0.022 (3)	0.012 (2)	0.017 (3)
C13	0.118 (5)	0.071 (4)	0.034 (3)	−0.030 (4)	0.031 (3)	−0.013 (3)
C14	0.102 (5)	0.085 (5)	0.049 (3)	0.046 (4)	0.045 (3)	0.034 (3)
C15	0.028 (2)	0.033 (2)	0.0227 (18)	0.0033 (18)	0.0056 (15)	−0.0009 (16)
C16	0.061 (3)	0.085 (4)	0.036 (2)	0.028 (3)	0.021 (2)	0.025 (3)
C17	0.050 (3)	0.084 (4)	0.037 (2)	−0.031 (3)	0.018 (2)	−0.003 (3)
C18	0.100 (4)	0.048 (3)	0.036 (2)	0.001 (3)	0.028 (3)	−0.002 (2)

N1—C5	1.323 (5)	C11—C12	1.513 (6)
N1—C1	1.338 (5)	C12—H12A	0.9600
N2—C6	1.328 (5)	C12—H12B	0.9600
N2—C10	1.329 (5)	C12—H12C	0.9600
C1—C2	1.381 (5)	C13—H13A	0.9600
C1—H1	0.9300	C13—H13B	0.9600
C2—C3	1.382 (5)	C13—H13C	0.9600
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.385 (5)	C14—H14B	0.9600
C3—C11	1.526 (5)	C14—H14C	0.9600
C4—C5	1.395 (5)	C15—C16	1.510 (6)
C4—H4	0.9300	C15—C17	1.518 (6)
C5—C6	1.493 (5)	C15—C18	1.522 (6)
C6—C7	1.390 (5)	C16—H16A	0.9600
C7—C8	1.389 (5)	C16—H16B	0.9600
C7—H7	0.9300	C16—H16C	0.9600
C8—C9	1.382 (5)	C17—H17A	0.9600
C8—C15	1.529 (5)	C17—H17B	0.9600
C9—C10	1.381 (5)	C17—H17C	0.9600
C9—H9	0.9300	C18—H18A	0.9600
C10—H10	0.9300	C18—H18B	0.9600
C11—C14	1.500 (6)	C18—H18C	0.9600
C11—C13	1.503 (6)
C5—N1—C1	115.9 (3)	H12A—C12—H12B	109.5
C6—N2—C10	116.1 (3)	C11—C12—H12C	109.5
N1—C1—C2	124.2 (4)	H12A—C12—H12C	109.5
N1—C1—H1	117.9	H12B—C12—H12C	109.5
C2—C1—H1	117.9	C11—C13—H13A	109.5
C1—C2—C3	120.1 (3)	C11—C13—H13B	109.5
C1—C2—H2	119.9	H13A—C13—H13B	109.5
C3—C2—H2	119.9	C11—C13—H13C	109.5
C2—C3—C4	115.8 (3)	H13A—C13—H13C	109.5
C2—C3—C11	120.9 (3)	H13B—C13—H13C	109.5
C4—C3—C11	123.3 (3)	C11—C14—H14A	109.5
C3—C4—C5	120.4 (4)	C11—C14—H14B	109.5
C3—C4—H4	119.8	H14A—C14—H14B	109.5
C5—C4—H4	119.8	C11—C14—H14C	109.5
N1—C5—C4	123.5 (3)	H14A—C14—H14C	109.5
N1—C5—C6	115.7 (3)	H14B—C14—H14C	109.5
C4—C5—C6	120.8 (3)	C16—C15—C17	109.5 (4)
N2—C6—C7	123.1 (3)	C16—C15—C18	107.7 (4)
N2—C6—C5	115.6 (3)	C17—C15—C18	108.6 (4)
C7—C6—C5	121.3 (3)	C16—C15—C8	111.7 (3)
C8—C7—C6	120.7 (4)	C17—C15—C8	107.8 (3)
C8—C7—H7	119.7	C18—C15—C8	111.6 (4)
C6—C7—H7	119.7	C15—C16—H16A	109.5
C9—C8—C7	115.6 (3)	C15—C16—H16B	109.5
C9—C8—C15	122.0 (3)	H16A—C16—H16B	109.5
C7—C8—C15	122.4 (3)	C15—C16—H16C	109.5
C10—C9—C8	120.0 (3)	H16A—C16—H16C	109.5
C10—C9—H9	120.0	H16B—C16—H16C	109.5
C8—C9—H9	120.0	C15—C17—H17A	109.5
N2—C10—C9	124.5 (4)	C15—C17—H17B	109.5
N2—C10—H10	117.7	H17A—C17—H17B	109.5
C9—C10—H10	117.7	C15—C17—H17C	109.5
C14—C11—C13	107.2 (4)	H17A—C17—H17C	109.5
C14—C11—C12	109.0 (4)	H17B—C17—H17C	109.5
C13—C11—C12	109.6 (4)	C15—C18—H18A	109.5
C14—C11—C3	112.1 (3)	C15—C18—H18B	109.5
C13—C11—C3	111.0 (3)	H18A—C18—H18B	109.5
C12—C11—C3	107.9 (3)	C15—C18—H18C	109.5
C11—C12—H12A	109.5	H18A—C18—H18C	109.5
C11—C12—H12B	109.5	H18B—C18—H18C	109.5
C5—N1—C1—C2	1.9 (5)	C6—C7—C8—C9	−0.5 (5)
N1—C1—C2—C3	−1.7 (6)	C6—C7—C8—C15	176.8 (3)
C1—C2—C3—C4	0.1 (5)	C7—C8—C9—C10	0.1 (5)
C1—C2—C3—C11	177.7 (3)	C15—C8—C9—C10	−177.2 (3)
C2—C3—C4—C5	1.2 (5)	C6—N2—C10—C9	−0.2 (5)
C11—C3—C4—C5	−176.3 (3)	C8—C9—C10—N2	0.2 (6)
C1—N1—C5—C4	−0.5 (5)	C2—C3—C11—C14	171.5 (4)
C1—N1—C5—C6	−179.4 (3)	C4—C3—C11—C14	−11.1 (6)
C3—C4—C5—N1	−1.1 (5)	C2—C3—C11—C13	51.7 (5)
C3—C4—C5—C6	177.8 (3)	C4—C3—C11—C13	−131.0 (4)
C10—N2—C6—C7	−0.3 (5)	C2—C3—C11—C12	−68.5 (5)
C10—N2—C6—C5	179.4 (3)	C4—C3—C11—C12	108.9 (5)
N1—C5—C6—N2	179.2 (3)	C9—C8—C15—C16	−152.6 (4)
C4—C5—C6—N2	0.2 (5)	C7—C8—C15—C16	30.2 (5)
N1—C5—C6—C7	−1.1 (5)	C9—C8—C15—C17	87.1 (5)
C4—C5—C6—C7	179.9 (3)	C7—C8—C15—C17	−90.1 (4)
N2—C6—C7—C8	0.6 (5)	C9—C8—C15—C18	−32.0 (5)
C5—C6—C7—C8	−179.0 (3)	C7—C8—C15—C18	150.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···N1i	.	2.74	3.637 (4)	155
C12—H12A···Cg2ii	.	.	3.78	140
C1—H1···Cg1ii	.	.	3.40	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯N1i		2.74	3.637 (4)	155
C12—H12A⋯Cg2ii			3.78	140
C1—H1⋯Cg1ii			3.40	137

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the N1,C1–C5 and N2,C6–C10 rings, respectively.