1,4-Bis[4-(dimethyl-silyl)phen-yl]benzene.

The complete molecule of the title compound, C(22)H(26)Si(2), is generated by a crystallographic centre of symmetry. The central benzene ring makes a dihedral angle of 26.7 (4)° with the 4-(dimethyl-silyl)phenyl ring. There are weak C-H⋯π inter-actions in the crystal structure.

Related literature

For applications of p-terphenyl derivatives as laser dyes, see: Craig et al. (1992 ▶), as light-emitting materials, see: Spiliopoulos et al. (2002 ▶) and as liquid crystalline materials, see: Yam et al. (1993 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶); Although p-terphenyls containing silyl groups have been reported (Feng et al., 2007 ▶), their crystal structures have not yet been determined.

Experimental

Crystal data

C22H26Si2

M = 346.61

Monoclinic,

a = 15.143 (3) Å

b = 7.7263 (15) Å

c = 9.1285 (18) Å

β = 107.52 (3)°

V = 1018.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 173 K

0.20 × 0.18 × 0.08 mm

Data collection

Rigaku Saturn724+ CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.966, T max = 0.986

7661 measured reflections

2218 independent reflections

1937 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.133

S = 1.21

2218 reflections

115 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010883/fb2186sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010883/fb2186Isup2.hkl

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

C22H26Si2	F(000) = 372
Mr = 346.61	Dx = 1.130 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 347 reflections
a = 15.143 (3) Å	θ = 2.2–27.5°
b = 7.7263 (15) Å	µ = 0.18 mm−1
c = 9.1285 (18) Å	T = 173 K
β = 107.52 (3)°	Plate, colorless
V = 1018.5 (3) Å3	0.20 × 0.18 × 0.08 mm
Z = 2

Rigaku Saturn724+ CCD diffractometer	2218 independent reflections
Radiation source: fine-focus sealed tube	1937 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans at fixed χ = 45°	θmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	h = −19→19
Tmin = 0.966, Tmax = 0.986	k = −9→9
7661 measured reflections	l = −7→11

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)] = 0.071	Hydrogen site location: difference Fourier map
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.21	w = 1/[σ2(Fo2) + (0.0276P)2 + 0.8805P] where P = (Fo2 + 2Fc2)/3
2218 reflections	(Δ/σ)max < 0.001
115 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.21 e Å−3
46 constraints

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Si1	0.35065 (5)	0.48948 (10)	0.54899 (8)	0.0361 (2)
C1	0.26293 (17)	0.4896 (3)	0.6572 (3)	0.0312 (5)
C2	0.17225 (18)	0.4309 (3)	0.5939 (3)	0.0341 (6)
H2A	0.1533	0.3895	0.4911	0.041*
C3	0.10866 (17)	0.4313 (3)	0.6768 (3)	0.0338 (6)
H3A	0.0474	0.3906	0.6299	0.041*
C4	0.13394 (16)	0.4907 (3)	0.8282 (3)	0.0288 (5)
C5	0.22485 (18)	0.5474 (4)	0.8935 (3)	0.0357 (6)
H5A	0.2441	0.5869	0.9968	0.043*
C6	0.28736 (18)	0.5469 (4)	0.8098 (3)	0.0365 (6)
H6A	0.3487	0.5866	0.8572	0.044*
C7	0.4368 (2)	0.3127 (5)	0.6203 (4)	0.0660 (11)
H7A	0.4832	0.3164	0.5651	0.099*
H7B	0.4051	0.2006	0.6028	0.099*
H7C	0.4674	0.3283	0.7305	0.099*
C8	0.2933 (2)	0.4691 (4)	0.3401 (3)	0.0468 (7)
H8A	0.2475	0.5617	0.3060	0.070*
H8B	0.2624	0.3565	0.3182	0.070*
H8C	0.3398	0.4785	0.2854	0.070*
C9	0.06529 (16)	0.4952 (3)	0.9166 (3)	0.0292 (5)
C10	0.07421 (17)	0.6139 (3)	1.0364 (3)	0.0319 (6)
H10A	0.1249	0.6924	1.0622	0.038*
C11	0.01023 (17)	0.6186 (3)	1.1179 (3)	0.0322 (6)
H11A	0.0178	0.7004	1.1985	0.039*
H1	0.3948 (17)	0.649 (3)	0.578 (3)	0.036 (7)*

	U11	U22	U33	U12	U13	U23
Si1	0.0341 (4)	0.0455 (5)	0.0312 (4)	−0.0040 (3)	0.0137 (3)	0.0030 (3)
C1	0.0319 (13)	0.0320 (13)	0.0314 (12)	0.0010 (11)	0.0119 (10)	0.0015 (11)
C2	0.0384 (14)	0.0381 (14)	0.0266 (12)	−0.0009 (12)	0.0113 (11)	−0.0023 (11)
C3	0.0295 (13)	0.0366 (14)	0.0345 (14)	−0.0019 (11)	0.0085 (11)	−0.0027 (11)
C4	0.0300 (12)	0.0265 (12)	0.0298 (12)	0.0007 (10)	0.0086 (9)	−0.0002 (10)
C5	0.0359 (14)	0.0432 (16)	0.0281 (13)	−0.0026 (12)	0.0100 (10)	−0.0044 (11)
C6	0.0308 (13)	0.0426 (15)	0.0364 (14)	−0.0037 (12)	0.0106 (11)	−0.0023 (12)
C7	0.0479 (19)	0.094 (3)	0.065 (2)	0.0250 (19)	0.0313 (17)	0.026 (2)
C8	0.0528 (18)	0.0535 (19)	0.0370 (15)	−0.0004 (15)	0.0178 (13)	−0.0022 (13)
C9	0.0294 (12)	0.0298 (13)	0.0280 (11)	0.0030 (11)	0.0079 (9)	0.0045 (10)
C10	0.0295 (12)	0.0337 (13)	0.0319 (13)	−0.0033 (11)	0.0082 (10)	−0.0032 (10)
C11	0.0351 (14)	0.0331 (14)	0.0287 (12)	−0.0025 (11)	0.0101 (11)	−0.0037 (10)

Si1—C8	1.848 (3)	C6—H6A	0.9500
Si1—C7	1.865 (3)	C7—H7A	0.9800
Si1—C1	1.879 (2)	C7—H7B	0.9800
Si1—H1	1.39 (3)	C7—H7C	0.9800
C1—C2	1.395 (3)	C8—H8A	0.9800
C1—C6	1.401 (3)	C8—H8B	0.9800
C2—C3	1.393 (3)	C8—H8C	0.9800
C2—H2A	0.9500	C9—C11i	1.401 (3)
C3—C4	1.396 (3)	C9—C10	1.402 (3)
C3—H3A	0.9500	C10—C11	1.388 (3)
C4—C5	1.396 (3)	C10—H10A	0.9500
C4—C9	1.496 (3)	C11—C9i	1.401 (3)
C5—C6	1.384 (3)	C11—H11A	0.9500
C5—H5A	0.9500
C8—Si1—C7	111.07 (16)	C1—C6—H6A	119.0
C8—Si1—C1	110.83 (12)	Si1—C7—H7A	109.5
C7—Si1—C1	110.34 (13)	Si1—C7—H7B	109.5
C8—Si1—H1	108.8 (10)	H7A—C7—H7B	109.5
C7—Si1—H1	109.7 (10)	Si1—C7—H7C	109.5
C1—Si1—H1	106.0 (10)	H7A—C7—H7C	109.5
C2—C1—C6	116.6 (2)	H7B—C7—H7C	109.5
C2—C1—Si1	123.04 (18)	Si1—C8—H8A	109.5
C6—C1—Si1	120.39 (19)	Si1—C8—H8B	109.5
C3—C2—C1	122.0 (2)	H8A—C8—H8B	109.5
C3—C2—H2A	119.0	Si1—C8—H8C	109.5
C1—C2—H2A	119.0	H8A—C8—H8C	109.5
C2—C3—C4	120.7 (2)	H8B—C8—H8C	109.5
C2—C3—H3A	119.7	C11i—C9—C10	117.8 (2)
C4—C3—H3A	119.7	C11i—C9—C4	121.1 (2)
C5—C4—C3	117.8 (2)	C10—C9—C4	121.1 (2)
C5—C4—C9	121.3 (2)	C11—C10—C9	121.1 (2)
C3—C4—C9	120.9 (2)	C11—C10—H10A	119.5
C6—C5—C4	121.0 (2)	C9—C10—H10A	119.5
C6—C5—H5A	119.5	C10—C11—C9i	121.1 (2)
C4—C5—H5A	119.5	C10—C11—H11A	119.4
C5—C6—C1	122.0 (2)	C9i—C11—H11A	119.4
C5—C6—H6A	119.0
C8—Si1—C1—C2	17.6 (3)	C4—C5—C6—C1	−0.2 (4)
C7—Si1—C1—C2	−105.9 (3)	C2—C1—C6—C5	−0.7 (4)
C8—Si1—C1—C6	−163.7 (2)	Si1—C1—C6—C5	−179.4 (2)
C7—Si1—C1—C6	72.8 (3)	C5—C4—C9—C11i	−154.1 (2)
C6—C1—C2—C3	0.8 (4)	C3—C4—C9—C11i	26.7 (4)
Si1—C1—C2—C3	179.6 (2)	C5—C4—C9—C10	26.2 (4)
C1—C2—C3—C4	−0.2 (4)	C3—C4—C9—C10	−153.1 (2)
C2—C3—C4—C5	−0.7 (4)	C11i—C9—C10—C11	−0.1 (4)
C2—C3—C4—C9	178.6 (2)	C4—C9—C10—C11	179.7 (2)
C3—C4—C5—C6	0.9 (4)	C9—C10—C11—C9i	0.1 (4)
C9—C4—C5—C6	−178.4 (2)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8b···Cg1ii	0.98	2.86	3.826 (3)	171
C10—H10a···Cg1iii	0.95	2.98	3.788 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8b⋯Cg1i	0.98	2.86	3.826 (3)	171
C10—H10a⋯Cg1ii	0.95	2.98	3.788 (3)	143

Symmetry codes: (i) ; (ii) .