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ISSN: 2056-9890

1,4-Bis(di­methyl­silyl)-2,5-di­phenyl­benzene

aBeijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China, bGraduate School of the Chinese Academy of Sciences, Beijing 100049, People's Republic of China, and cSchool of Chemical and Environmental Engineering, Beijing Technology and Business University, Beijing 100037, People's Republic of China
*Correspondence e-mail: caihong@iccas.ac.cn

(Received 23 February 2010; accepted 23 March 2010; online 27 March 2010)

The mol­ecule of the title compound, C22H26Si2, 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[Feng, X., Pisula, W. & Müllen, K. (2007). J. Am. Chem. Soc. 129, 14116-14117.]).

[Scheme 1]

Experimental

Crystal data
  • C22H26Si2

  • Mr = 346.61

  • Monoclinic, C 2/c

  • 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[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.905, Tmax = 0.980

  • 4032 measured reflections

  • 2220 independent reflections

  • 2009 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 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[Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As part of our ongoing investigation on the effect of silyl substituents on the photophysics of p-terphenyls, we present the title compound bearing silyl substituents at the central phenyl ring (2,5-positions). Though analogues of the title compound were reported elsewhere (Feng et al., 2007), their structures were not fully studied. The molecular structure of the title compound is shown in Fig.1. It is centrosymmetric, the centroid of the central benzene ring is located on an inversion center at 0,1,0. The dihedral angle between the benzene ring and phenyl substituents is 67.7 (2)°. The crystal packing is mainly stabilized by van der Waals forces.

Related literature top

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

Experimental top

A solution of 2,5-dibromo-1,4-diphenylbenzene (120 mg, 0.31 mmol) in anhydrous THF (10 ml) was added dropwise to a hexane solution of n-BuLi (2.5 M, 0.44 ml, 1.08 mmol) dropwise at -78 °C. The reaction mixture was stirred for 1 h and dimethylchlorosilane (118 mg, 1.24 mmol) was added via syringe at the same temperature and the mixture was allowed to warm to room temperature and stirred overnight. After being quenched with saturated NaHCO3 solution, the mixture was extracted with Et2O. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The mixture was passed through a silica gel column with hexane as an eluent, followed by further purification by recrystallization from ethanol to give 98 mg of the white product in 91% yield.

Refinement top

All H-atoms were located in electron-density difference maps. Carbon-bound H atoms were placed geometrically in idealized positions and refined using a riding model with C—H (methyl) 0.98, C—H (aromatic) 0.95 Å and with Uiso(H) =1.2Ueq(C). Located in the electron-density difference map H atom from the silyl group was refined using riding model with Uiso(H) =1.2Ueq(Si).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme. The unlabelled atoms can be generated by the symmetry operation -x, -y+2, -z.
1,4-Bis(dimethylsilyl)-2,5-diphenylbenzene top
Crystal data top
C22H26Si2F(000) = 744
Mr = 346.61Dx = 1.175 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4032 reflections
a = 14.8966 (3) Åθ = 2.7–27.5°
b = 6.0132 (1) ŵ = 0.18 mm1
c = 26.1211 (6) ÅT = 173 K
β = 123.166 (1)°Plate, colorless
V = 1958.64 (7) Å30.56 × 0.39 × 0.11 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
2220 independent reflections
Radiation source: rotating anode2009 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω scans at fixed χ = 45°θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1919
Tmin = 0.905, Tmax = 0.980k = 77
4032 measured reflectionsl = 3333
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-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 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C22H26Si2V = 1958.64 (7) Å3
Mr = 346.61Z = 4
Monoclinic, C2/cMo Kα radiation
a = 14.8966 (3) ŵ = 0.18 mm1
b = 6.0132 (1) ÅT = 173 K
c = 26.1211 (6) Å0.56 × 0.39 × 0.11 mm
β = 123.166 (1)°
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
2220 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
2009 reflections with I > 2σ(I)
Tmin = 0.905, Tmax = 0.980Rint = 0.028
4032 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.22Δρmax = 0.40 e Å3
2220 reflectionsΔρmin = 0.22 e Å3
111 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.03046 (4)0.64331 (9)0.08538 (2)0.02208 (16)
H10.05900.51940.12230.026*
C10.00698 (14)0.8349 (3)0.03690 (8)0.0207 (4)
C20.09110 (15)0.8753 (3)0.02358 (8)0.0220 (4)
H20.15450.78870.04030.026*
C30.08631 (14)0.9637 (3)0.06040 (8)0.0202 (4)
C40.18299 (14)0.9316 (3)0.12353 (8)0.0208 (4)
C50.21644 (16)1.0962 (3)0.16753 (9)0.0276 (4)
H50.17621.22980.15780.033*
C60.30788 (17)1.0685 (4)0.22563 (9)0.0314 (5)
H60.32921.18190.25550.038*
C70.36813 (15)0.8762 (4)0.24023 (8)0.0285 (4)
H70.43140.85820.27980.034*
C80.33562 (16)0.7103 (4)0.19677 (9)0.0310 (5)
H80.37630.57730.20670.037*
C90.24395 (16)0.7377 (3)0.13896 (8)0.0261 (4)
H90.22230.62310.10940.031*
C100.0605 (2)0.8174 (4)0.13337 (10)0.0375 (5)
H10A0.12490.90650.10680.056*
H10B0.00020.91640.15920.056*
H10C0.07260.72090.15930.056*
C110.14236 (19)0.4490 (4)0.03752 (10)0.0377 (5)
H11A0.15650.35950.06370.057*
H11B0.12300.35090.01510.057*
H11C0.20680.53380.00840.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0233 (3)0.0233 (3)0.0197 (3)0.0028 (2)0.0118 (2)0.0051 (2)
C10.0221 (9)0.0217 (9)0.0194 (8)0.0021 (7)0.0120 (7)0.0018 (7)
C20.0213 (9)0.0241 (9)0.0199 (8)0.0012 (7)0.0110 (7)0.0005 (7)
C30.0208 (9)0.0228 (9)0.0162 (8)0.0024 (7)0.0096 (7)0.0009 (7)
C40.0190 (8)0.0251 (9)0.0170 (8)0.0005 (7)0.0090 (7)0.0016 (7)
C50.0268 (10)0.0246 (10)0.0242 (9)0.0041 (8)0.0094 (8)0.0009 (8)
C60.0315 (11)0.0333 (11)0.0202 (9)0.0000 (9)0.0082 (8)0.0051 (8)
C70.0202 (9)0.0406 (12)0.0174 (8)0.0028 (8)0.0056 (7)0.0015 (8)
C80.0259 (10)0.0365 (11)0.0242 (9)0.0115 (9)0.0096 (8)0.0038 (9)
C90.0276 (10)0.0274 (10)0.0199 (9)0.0051 (8)0.0108 (8)0.0020 (8)
C100.0482 (13)0.0381 (12)0.0341 (11)0.0045 (10)0.0275 (11)0.0008 (10)
C110.0454 (13)0.0356 (12)0.0367 (12)0.0103 (10)0.0254 (11)0.0035 (10)
Geometric parameters (Å, º) top
Si1—C111.851 (2)C6—C71.383 (3)
Si1—C101.866 (2)C6—H60.9500
Si1—C11.8812 (19)C7—C81.385 (3)
Si1—H11.3623C7—H70.9500
C1—C21.400 (2)C8—C91.384 (3)
C1—C31.405 (3)C8—H80.9500
C2—C3i1.394 (3)C9—H90.9500
C2—H20.9500C10—H10A0.9800
C3—C2i1.394 (3)C10—H10B0.9800
C3—C41.494 (2)C10—H10C0.9800
C4—C51.386 (3)C11—H11A0.9800
C4—C91.395 (3)C11—H11B0.9800
C5—C61.387 (3)C11—H11C0.9800
C5—H50.9500
C11—Si1—C10110.47 (11)C5—C6—H6119.9
C11—Si1—C1111.24 (9)C6—C7—C8119.55 (17)
C10—Si1—C1108.04 (10)C6—C7—H7120.2
C11—Si1—H1107.7C8—C7—H7120.2
C10—Si1—H1109.4C9—C8—C7120.16 (19)
C1—Si1—H1110.0C9—C8—H8119.9
C2—C1—C3117.29 (16)C7—C8—H8119.9
C2—C1—Si1118.99 (14)C8—C9—C4120.83 (18)
C3—C1—Si1123.17 (13)C8—C9—H9119.6
C3i—C2—C1123.17 (17)C4—C9—H9119.6
C3i—C2—H2118.4Si1—C10—H10A109.5
C1—C2—H2118.4Si1—C10—H10B109.5
C2i—C3—C1119.54 (16)H10A—C10—H10B109.5
C2i—C3—C4117.97 (16)Si1—C10—H10C109.5
C1—C3—C4122.47 (16)H10A—C10—H10C109.5
C5—C4—C9118.37 (16)H10B—C10—H10C109.5
C5—C4—C3121.00 (17)Si1—C11—H11A109.5
C9—C4—C3120.59 (17)Si1—C11—H11B109.5
C4—C5—C6120.91 (18)H11A—C11—H11B109.5
C4—C5—H5119.5Si1—C11—H11C109.5
C6—C5—H5119.5H11A—C11—H11C109.5
C7—C6—C5120.18 (19)H11B—C11—H11C109.5
C7—C6—H6119.9
C11—Si1—C1—C223.44 (19)C1—C3—C4—C5114.5 (2)
C10—Si1—C1—C297.97 (17)C2i—C3—C4—C9110.8 (2)
C11—Si1—C1—C3165.30 (16)C1—C3—C4—C967.7 (2)
C10—Si1—C1—C373.29 (18)C9—C4—C5—C60.4 (3)
C3—C1—C2—C3i0.6 (3)C3—C4—C5—C6178.25 (18)
Si1—C1—C2—C3i171.16 (14)C4—C5—C6—C70.9 (3)
C2—C1—C3—C2i0.6 (3)C5—C6—C7—C81.0 (3)
Si1—C1—C3—C2i170.81 (14)C6—C7—C8—C90.6 (3)
C2—C1—C3—C4177.92 (17)C7—C8—C9—C40.0 (3)
Si1—C1—C3—C410.7 (3)C5—C4—C9—C80.0 (3)
C2i—C3—C4—C567.0 (2)C3—C4—C9—C8177.82 (19)
Symmetry code: (i) x, y+2, z.

Experimental details

Crystal data
Chemical formulaC22H26Si2
Mr346.61
Crystal system, space groupMonoclinic, C2/c
Temperature (K)173
a, b, c (Å)14.8966 (3), 6.0132 (1), 26.1211 (6)
β (°) 123.166 (1)
V3)1958.64 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.56 × 0.39 × 0.11
Data collection
DiffractometerRigaku R-AXIS RAPID IP area-detector
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.905, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
4032, 2220, 2009
Rint0.028
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.118, 1.22
No. of reflections2220
No. of parameters111
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.22

Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the National Science Foundation of China (NSFC, Nos. 50673094 and 20774102).

References

First citationFeng, X., Pisula, W. & Müllen, K. (2007). J. Am. Chem. Soc. 129, 14116–14117.  Web of Science CrossRef PubMed CAS Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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COMMUNICATIONS
ISSN: 2056-9890
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