5,5'-Bis[(trimethyl-silyl)meth-yl]-2,2'-bipyridine.

The mol-ecule of the title compound, C(18)H(28)N(2)Si(2), occupies a special position on an inversion centre. The Si-CH(2)-C(ipso) plane is approximately orthogonal to the plane of the pyridine rings, the corresponding dihedral angle being 82.0 (2)°.

Related literature

For related chemistry, see: Fraser et al. (1997 ▶); Hochwimmer et al.(1998 ▶); Perkins et al. (2006 ▶); Schubert et al. (1998 ▶). For recently reported similar structures, see: Khan et al. (2004 ▶); Lindoy et al. (2204). For related literature, see: Lindoy et al. (2004 ▶).

Experimental

Crystal data

C18H28N2Si2

M = 328.60

Triclinic,

a = 6.279 (3) Å

b = 6.575 (3) Å

c = 14.030 (6) Å

α = 76.599 (7)°

β = 88.415 (7)°

γ = 64.859 (6)°

V = 508.4 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.17 mm−1

T = 293 (2) K

0.25 × 0.15 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.973, T max = 0.974

4192 measured reflections

2057 independent reflections

1294 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.192

S = 1.04

2057 reflections

123 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT and XPREP (Bruker, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807052154/ya2054sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807052154/ya2054Isup2.hkl

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

C18H28N2Si2	Z = 1
Mr = 328.60	F000 = 178
Triclinic, P1	Dx = 1.073 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71069 Å
a = 6.279 (3) Å	Cell parameters from 1147 reflections
b = 6.575 (3) Å	θ = 0.9–26.4º
c = 14.030 (6) Å	µ = 0.17 mm−1
α = 76.599 (7)º	T = 293 (2) K
β = 88.415 (7)º	Prism, colourless
γ = 64.859 (6)º	0.25 × 0.15 × 0.10 mm
V = 508.4 (4) Å3

Bruker SMART 1000 CCD area-detector diffractometer	2057 independent reflections
Radiation source: fine-focus sealed tube	1294 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.042
T = 293(2) K	θmax = 26.4º
φ and ω scans	θmin = 3.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.973, Tmax = 0.974	k = −8→8
4192 measured reflections	l = −17→17

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)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.192	w = 1/[σ2(Fo2) + (0.093P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.007
2057 reflections	Δρmax = 0.36 e Å−3
123 parameters	Δρmin = −0.16 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. An empirical absorption correction determined with SADABS (Sheldrick, 1996) was applied to the data. The data integration and reduction were undertaken with SAINT and XPREP (Bruker, 2001). The data reduction included the application of Lorentz and polarization corrections. The reflection data were merged including Fridel opposites. The structure was solved in the space group P-1 by direct methods with SHELXS97 (Sheldrick, 1997) within the WinG-X (Farrugia, 1999) interface and extended and refined with SHELXL97 (Sheldrick 1997). Anisotropic thermal parameters were refined for the non-hydrogen atoms. All aromatic and methylene H atoms were located and refined with isotropic thermal parameters. Methyl H atoms were constrained as riding atoms, fixed to the parent C atom with a distance of 0.96 Å. Uiso values were set to 1.5 Ueq of the parent C atom.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
Si1	0.78941 (12)	0.61211 (12)	0.82038 (5)	0.0664 (3)
C1	0.5188 (4)	1.3836 (4)	0.52943 (15)	0.0544 (5)
N1	0.7386 (3)	1.2150 (4)	0.53910 (15)	0.0681 (6)
C4	0.6028 (4)	0.9417 (4)	0.63513 (16)	0.0594 (6)
C2	0.3355 (4)	1.3408 (5)	0.57193 (18)	0.0646 (7)
C5	0.7751 (5)	1.0028 (5)	0.59098 (19)	0.0686 (7)
C6	0.6608 (5)	0.6974 (5)	0.69012 (18)	0.0660 (7)
C3	0.3787 (5)	1.1207 (5)	0.62426 (18)	0.0673 (7)
C9	0.5840 (5)	0.8130 (5)	0.8897 (2)	0.0951 (9)
H9A	0.5359	0.9699	0.8525	0.143*
H9B	0.6620	0.7910	0.9517	0.143*
H9C	0.4478	0.7823	0.9009	0.143*
C7	0.8328 (6)	0.3086 (5)	0.8742 (2)	0.1086 (11)
H7B	0.8969	0.2606	0.9412	0.163*
H7C	0.9400	0.2082	0.8371	0.163*
H7A	0.6838	0.3008	0.8719	0.163*
C8	1.0830 (5)	0.6243 (6)	0.8206 (2)	0.1070 (11)
H8A	1.0637	0.7764	0.7865	0.160*
H8B	1.1908	0.5123	0.7882	0.160*
H8C	1.1446	0.5904	0.8871	0.160*
H6A	0.773 (4)	0.589 (4)	0.6581 (18)	0.074 (8)*
H6B	0.513 (5)	0.676 (4)	0.6947 (18)	0.087 (8)*
H5	0.923 (4)	0.883 (4)	0.5873 (17)	0.075 (7)*
H3	0.243 (5)	1.082 (4)	0.6515 (19)	0.093 (8)*
H2	0.179 (4)	1.470 (4)	0.5684 (16)	0.067 (7)*

	U11	U22	U33	U12	U13	U23
Si1	0.0679 (5)	0.0709 (5)	0.0656 (5)	−0.0393 (4)	0.0016 (3)	−0.0070 (3)
C1	0.0476 (13)	0.0684 (14)	0.0500 (12)	−0.0274 (12)	0.0054 (10)	−0.0148 (10)
N1	0.0537 (12)	0.0677 (13)	0.0784 (14)	−0.0267 (10)	0.0164 (10)	−0.0096 (11)
C4	0.0635 (15)	0.0713 (15)	0.0509 (12)	−0.0374 (13)	0.0049 (11)	−0.0123 (11)
C2	0.0457 (13)	0.0728 (17)	0.0686 (15)	−0.0243 (13)	0.0056 (11)	−0.0077 (13)
C5	0.0546 (15)	0.0663 (16)	0.0765 (17)	−0.0221 (13)	0.0141 (12)	−0.0104 (14)
C6	0.0720 (18)	0.0705 (16)	0.0665 (16)	−0.0400 (15)	0.0085 (13)	−0.0187 (13)
C3	0.0567 (15)	0.0804 (18)	0.0696 (16)	−0.0381 (14)	0.0088 (12)	−0.0107 (13)
C9	0.108 (2)	0.116 (2)	0.0779 (19)	−0.060 (2)	0.0187 (17)	−0.0319 (18)
C7	0.127 (3)	0.084 (2)	0.110 (2)	−0.052 (2)	−0.006 (2)	−0.0014 (18)
C8	0.080 (2)	0.136 (3)	0.113 (3)	−0.061 (2)	−0.0108 (18)	−0.015 (2)

Si1—C9	1.853 (3)	C5—H5	0.94 (2)
Si1—C7	1.864 (3)	C6—H6A	0.95 (2)
Si1—C6	1.878 (3)	C6—H6B	1.00 (3)
Si1—C8	1.879 (3)	C3—H3	1.03 (3)
C1—N1	1.339 (3)	C9—H9A	0.9600
C1—C2	1.385 (3)	C9—H9B	0.9600
C1—C1i	1.483 (4)	C9—H9C	0.9600
N1—C5	1.340 (3)	C7—H7B	0.9600
C4—C3	1.382 (4)	C7—H7C	0.9600
C4—C5	1.390 (3)	C7—H7A	0.9600
C4—C6	1.501 (4)	C8—H8A	0.9600
C2—C3	1.376 (3)	C8—H8B	0.9600
C2—H2	0.98 (2)	C8—H8C	0.9600
C9—Si1—C7	111.14 (16)	Si1—C6—H6B	105.3 (15)
C9—Si1—C6	109.21 (14)	H6A—C6—H6B	110 (2)
C7—Si1—C6	107.55 (14)	C2—C3—C4	120.9 (2)
C9—Si1—C8	110.33 (15)	C2—C3—H3	120.9 (15)
C7—Si1—C8	109.30 (16)	C4—C3—H3	118.1 (15)
C6—Si1—C8	109.25 (13)	Si1—C9—H9A	109.5
N1—C1—C2	121.3 (2)	Si1—C9—H9B	109.5
N1—C1—C1i	116.9 (2)	H9A—C9—H9B	109.5
C2—C1—C1i	121.8 (2)	Si1—C9—H9C	109.5
C1—N1—C5	117.7 (2)	H9A—C9—H9C	109.5
C3—C4—C5	115.2 (2)	H9B—C9—H9C	109.5
C3—C4—C6	123.4 (2)	Si1—C7—H7B	109.5
C5—C4—C6	121.4 (2)	Si1—C7—H7C	109.5
C3—C2—C1	119.6 (2)	H7B—C7—H7C	109.5
C3—C2—H2	120.8 (13)	Si1—C7—H7A	109.5
C1—C2—H2	119.5 (13)	H7B—C7—H7A	109.5
N1—C5—C4	125.4 (2)	H7C—C7—H7A	109.5
N1—C5—H5	115.7 (15)	Si1—C8—H8A	109.5
C4—C5—H5	118.0 (15)	Si1—C8—H8B	109.5
C4—C6—Si1	115.70 (17)	H8A—C8—H8B	109.5
C4—C6—H6A	111.0 (14)	Si1—C8—H8C	109.5
Si1—C6—H6A	105.7 (14)	H8A—C8—H8C	109.5
C4—C6—H6B	108.8 (15)	H8B—C8—H8C	109.5