1,4-Bis(dimethyl-silyl)-2,5-diphenyl-benzene.

The mol-ecule of the title compound, C(22)H(26)Si(2), is centrosymmetric. The dihedral angle between the central benzene ring and its phenyl substituents is 67.7 (2)°. The crystal packing is stabilized by van der Waals forces.

Related literature

For investigations on the effect of silyl substituents on the photophysics of p-terphenyls, see: Feng et al. (2007 ▶).

Experimental

Crystal data

C22H26Si2

M = 346.61

Monoclinic,

a = 14.8966 (3) Å

b = 6.0132 (1) Å

c = 26.1211 (6) Å

β = 123.166 (1)°

V = 1958.64 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 173 K

0.56 × 0.39 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.905, T max = 0.980

4032 measured reflections

2220 independent reflections

2009 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.118

S = 1.22

2220 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.22 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2001 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010913/gk2260sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010913/gk2260Isup2.hkl

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

C22H26Si2	F(000) = 744
Mr = 346.61	Dx = 1.175 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4032 reflections
a = 14.8966 (3) Å	θ = 2.7–27.5°
b = 6.0132 (1) Å	µ = 0.18 mm−1
c = 26.1211 (6) Å	T = 173 K
β = 123.166 (1)°	Plate, colorless
V = 1958.64 (7) Å3	0.56 × 0.39 × 0.11 mm
Z = 4

Rigaku R-AXIS RAPID IP area-detector diffractometer	2220 independent reflections
Radiation source: rotating anode	2009 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans at fixed χ = 45°	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −19→19
Tmin = 0.905, Tmax = 0.980	k = −7→7
4032 measured reflections	l = −33→33

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.22	w = 1/[σ2(Fo2) + (0.0432P)2 + 2.0232P] where P = (Fo2 + 2Fc2)/3
2220 reflections	(Δ/σ)max < 0.001
111 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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 > 2σ(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	−0.03046 (4)	0.64331 (9)	0.08538 (2)	0.02208 (16)
H1	0.0590	0.5194	0.1223	0.026*
C1	−0.00698 (14)	0.8349 (3)	0.03690 (8)	0.0207 (4)
C2	−0.09110 (15)	0.8753 (3)	−0.02358 (8)	0.0220 (4)
H2	−0.1545	0.7887	−0.0403	0.026*
C3	0.08631 (14)	0.9637 (3)	0.06040 (8)	0.0202 (4)
C4	0.18299 (14)	0.9316 (3)	0.12353 (8)	0.0208 (4)
C5	0.21644 (16)	1.0962 (3)	0.16753 (9)	0.0276 (4)
H5	0.1762	1.2298	0.1578	0.033*
C6	0.30788 (17)	1.0685 (4)	0.22563 (9)	0.0314 (5)
H6	0.3292	1.1819	0.2555	0.038*
C7	0.36813 (15)	0.8762 (4)	0.24023 (8)	0.0285 (4)
H7	0.4314	0.8582	0.2798	0.034*
C8	0.33562 (16)	0.7103 (4)	0.19677 (9)	0.0310 (5)
H8	0.3763	0.5773	0.2067	0.037*
C9	0.24395 (16)	0.7377 (3)	0.13896 (8)	0.0261 (4)
H9	0.2223	0.6231	0.1094	0.031*
C10	−0.0605 (2)	0.8174 (4)	0.13337 (10)	0.0375 (5)
H10A	−0.1249	0.9065	0.1068	0.056*
H10B	0.0002	0.9164	0.1592	0.056*
H10C	−0.0726	0.7209	0.1593	0.056*
C11	−0.14236 (19)	0.4490 (4)	0.03752 (10)	0.0377 (5)
H11A	−0.1565	0.3595	0.0637	0.057*
H11B	−0.1230	0.3509	0.0151	0.057*
H11C	−0.2068	0.5338	0.0084	0.057*

	U11	U22	U33	U12	U13	U23
Si1	0.0233 (3)	0.0233 (3)	0.0197 (3)	0.0028 (2)	0.0118 (2)	0.0051 (2)
C1	0.0221 (9)	0.0217 (9)	0.0194 (8)	0.0021 (7)	0.0120 (7)	0.0018 (7)
C2	0.0213 (9)	0.0241 (9)	0.0199 (8)	−0.0012 (7)	0.0110 (7)	−0.0005 (7)
C3	0.0208 (9)	0.0228 (9)	0.0162 (8)	0.0024 (7)	0.0096 (7)	0.0009 (7)
C4	0.0190 (8)	0.0251 (9)	0.0170 (8)	0.0005 (7)	0.0090 (7)	0.0016 (7)
C5	0.0268 (10)	0.0246 (10)	0.0242 (9)	0.0041 (8)	0.0094 (8)	−0.0009 (8)
C6	0.0315 (11)	0.0333 (11)	0.0202 (9)	0.0000 (9)	0.0082 (8)	−0.0051 (8)
C7	0.0202 (9)	0.0406 (12)	0.0174 (8)	0.0028 (8)	0.0056 (7)	0.0015 (8)
C8	0.0259 (10)	0.0365 (11)	0.0242 (9)	0.0115 (9)	0.0096 (8)	0.0038 (9)
C9	0.0276 (10)	0.0274 (10)	0.0199 (9)	0.0051 (8)	0.0108 (8)	−0.0020 (8)
C10	0.0482 (13)	0.0381 (12)	0.0341 (11)	0.0045 (10)	0.0275 (11)	0.0008 (10)
C11	0.0454 (13)	0.0356 (12)	0.0367 (12)	−0.0103 (10)	0.0254 (11)	−0.0035 (10)

Si1—C11	1.851 (2)	C6—C7	1.383 (3)
Si1—C10	1.866 (2)	C6—H6	0.9500
Si1—C1	1.8812 (19)	C7—C8	1.385 (3)
Si1—H1	1.3623	C7—H7	0.9500
C1—C2	1.400 (2)	C8—C9	1.384 (3)
C1—C3	1.405 (3)	C8—H8	0.9500
C2—C3i	1.394 (3)	C9—H9	0.9500
C2—H2	0.9500	C10—H10A	0.9800
C3—C2i	1.394 (3)	C10—H10B	0.9800
C3—C4	1.494 (2)	C10—H10C	0.9800
C4—C5	1.386 (3)	C11—H11A	0.9800
C4—C9	1.395 (3)	C11—H11B	0.9800
C5—C6	1.387 (3)	C11—H11C	0.9800
C5—H5	0.9500
C11—Si1—C10	110.47 (11)	C5—C6—H6	119.9
C11—Si1—C1	111.24 (9)	C6—C7—C8	119.55 (17)
C10—Si1—C1	108.04 (10)	C6—C7—H7	120.2
C11—Si1—H1	107.7	C8—C7—H7	120.2
C10—Si1—H1	109.4	C9—C8—C7	120.16 (19)
C1—Si1—H1	110.0	C9—C8—H8	119.9
C2—C1—C3	117.29 (16)	C7—C8—H8	119.9
C2—C1—Si1	118.99 (14)	C8—C9—C4	120.83 (18)
C3—C1—Si1	123.17 (13)	C8—C9—H9	119.6
C3i—C2—C1	123.17 (17)	C4—C9—H9	119.6
C3i—C2—H2	118.4	Si1—C10—H10A	109.5
C1—C2—H2	118.4	Si1—C10—H10B	109.5
C2i—C3—C1	119.54 (16)	H10A—C10—H10B	109.5
C2i—C3—C4	117.97 (16)	Si1—C10—H10C	109.5
C1—C3—C4	122.47 (16)	H10A—C10—H10C	109.5
C5—C4—C9	118.37 (16)	H10B—C10—H10C	109.5
C5—C4—C3	121.00 (17)	Si1—C11—H11A	109.5
C9—C4—C3	120.59 (17)	Si1—C11—H11B	109.5
C4—C5—C6	120.91 (18)	H11A—C11—H11B	109.5
C4—C5—H5	119.5	Si1—C11—H11C	109.5
C6—C5—H5	119.5	H11A—C11—H11C	109.5
C7—C6—C5	120.18 (19)	H11B—C11—H11C	109.5
C7—C6—H6	119.9
C11—Si1—C1—C2	23.44 (19)	C1—C3—C4—C5	−114.5 (2)
C10—Si1—C1—C2	−97.97 (17)	C2i—C3—C4—C9	−110.8 (2)
C11—Si1—C1—C3	−165.30 (16)	C1—C3—C4—C9	67.7 (2)
C10—Si1—C1—C3	73.29 (18)	C9—C4—C5—C6	−0.4 (3)
C3—C1—C2—C3i	−0.6 (3)	C3—C4—C5—C6	−178.25 (18)
Si1—C1—C2—C3i	171.16 (14)	C4—C5—C6—C7	0.9 (3)
C2—C1—C3—C2i	0.6 (3)	C5—C6—C7—C8	−1.0 (3)
Si1—C1—C3—C2i	−170.81 (14)	C6—C7—C8—C9	0.6 (3)
C2—C1—C3—C4	−177.92 (17)	C7—C8—C9—C4	0.0 (3)
Si1—C1—C3—C4	10.7 (3)	C5—C4—C9—C8	0.0 (3)
C2i—C3—C4—C5	67.0 (2)	C3—C4—C9—C8	177.82 (19)