Literature DB >> 23795066

6,12-Bis[(tri-cyclo-hexyl-sil-yl)ethyn-yl]indeno-[1,2-b]fluorene.

Bradley D Rose1, Lev N Zakharov, Michael M Haley.   

Abstract

The title compound, C60H76Si2, a formally anti-aromatic system containing 20-π electrons, contains a rare p-xylylene motif. This is displayed by the alternating short and long bonds. The outer rings possess nearly homogenous bond lengths. In the crystal, the molecules forms layers perpendicular to the c axis and within these layers there are two one-dimensional stacks with one stack that has a sp (2) carbon contact of 3.283 (6) Å, less than the sum of the van der Waals radii. The center of the mol-ecule sits on an inversion center.

Entities:  

Year:  2013        PMID: 23795066      PMCID: PMC3685047          DOI: 10.1107/S160053681301218X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For the synthetic procedure, see: Kendrick et al. (2012 ▶). For information about the indeno­fluorene mol­ecular framework, see: Fix et al. (2012 ▶) and about crystal packing, see: Anthony et al. (2010 ▶).

Experimental

Crystal data

C60H76Si2 M = 853.39 Monoclinic, a = 20.219 (7) Å b = 7.246 (2) Å c = 33.885 (11) Å β = 103.017 (7)° V = 4837 (3) Å3 Z = 4 Mo Kα radiation μ = 0.11 mm−1 T = 193 K 0.08 × 0.03 × 0.01 mm

Data collection

Bruker APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.991, T max = 0.999 22528 measured reflections 4268 independent reflections 2181 reflections with I > 2σ(I) R int = 0.176

Refinement

R[F 2 > 2σ(F 2)] = 0.076 wR(F 2) = 0.151 S = 1.01 4268 reflections 280 parameters H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.28 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: XS in SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: XL in SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681301218X/pk2470sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301218X/pk2470Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S160053681301218X/pk2470Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C60H76Si2F(000) = 1856
Mr = 853.39Dx = 1.172 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 547 reflections
a = 20.219 (7) Åθ = 2.6–15.4°
b = 7.246 (2) ŵ = 0.11 mm1
c = 33.885 (11) ÅT = 193 K
β = 103.017 (7)°Block, purple
V = 4837 (3) Å30.08 × 0.03 × 0.01 mm
Z = 4
Bruker APEX CCD area-detector diffractometer4268 independent reflections
Radiation source: fine-focus sealed tube2181 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.176
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −24→24
Tmin = 0.991, Tmax = 0.999k = −8→8
22528 measured reflectionsl = −40→40
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0419P)2] where P = (Fo2 + 2Fc2)/3
4268 reflections(Δ/σ)max = 0.001
280 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.28 e Å3
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.
xyzUiso*/Ueq
Si10.64679 (6)0.27756 (16)0.85715 (3)0.0270 (3)
C10.5070 (2)0.1499 (5)0.97336 (11)0.0288 (10)
H1A0.51230.24790.95570.035*
C20.5493 (2)−0.0092 (5)0.97752 (11)0.0246 (10)
C30.5413 (2)−0.1567 (5)1.00438 (11)0.0260 (10)
C40.5924 (2)−0.2973 (6)1.00215 (11)0.0286 (10)
C50.63048 (19)−0.2320 (5)0.97507 (10)0.0244 (9)
C60.60219 (19)−0.0535 (5)0.95896 (11)0.0249 (10)
C70.6839 (2)−0.3316 (6)0.96734 (12)0.0347 (11)
H7A0.7103−0.28520.94960.042*
C80.6983 (2)−0.5026 (6)0.98614 (13)0.0391 (12)
H8A0.7350−0.57390.98120.047*
C90.6603 (2)−0.5689 (6)1.01174 (13)0.0415 (12)
H9A0.6703−0.68701.02380.050*
C100.6070 (2)−0.4658 (6)1.02035 (12)0.0362 (11)
H10A0.5813−0.51161.03850.043*
C110.6207 (2)0.0464 (5)0.92737 (12)0.0270 (10)
C120.63409 (19)0.1298 (6)0.89918 (12)0.0280 (10)
C130.6609 (2)0.1232 (5)0.81513 (11)0.0298 (10)
H13A0.70430.05590.82630.036*
C140.6076 (2)−0.0260 (6)0.80074 (13)0.0441 (13)
H14A0.6024−0.10110.82430.053*
H14B0.56340.03370.78930.053*
C150.6257 (3)−0.1525 (6)0.76890 (13)0.0506 (14)
H15A0.6669−0.22390.78120.061*
H15B0.5882−0.24110.75950.061*
C160.6381 (2)−0.0457 (6)0.73328 (13)0.0490 (13)
H16A0.59520.01170.71860.059*
H16B0.6539−0.13070.71440.059*
C170.6908 (3)0.1026 (7)0.74695 (13)0.0551 (14)
H17A0.69560.17650.72320.066*
H17B0.73510.04360.75840.066*
C180.6726 (2)0.2297 (6)0.77841 (12)0.0451 (13)
H18A0.63100.29940.76600.054*
H18B0.70980.31980.78740.054*
C190.72462 (19)0.4184 (5)0.87874 (12)0.0272 (10)
H19A0.71830.46280.90560.033*
C200.7901 (2)0.3061 (5)0.88827 (12)0.0336 (11)
H20A0.78410.19950.90540.040*
H20B0.79900.25740.86270.040*
C210.8510 (2)0.4179 (6)0.90996 (13)0.0396 (12)
H21A0.89240.34050.91410.048*
H21B0.84460.45590.93690.048*
C220.8603 (2)0.5878 (6)0.88565 (13)0.0415 (12)
H22A0.89880.66170.90100.050*
H22B0.87140.54940.85990.050*
C230.7967 (2)0.7052 (6)0.87667 (13)0.0435 (12)
H23A0.80330.81040.85930.052*
H23B0.78870.75570.90230.052*
C240.7351 (2)0.5942 (5)0.85547 (13)0.0372 (12)
H24A0.74050.55930.82810.045*
H24B0.69410.67260.85210.045*
C250.5693 (2)0.4297 (6)0.84335 (12)0.0308 (11)
H25A0.57490.50910.82020.037*
C260.5644 (2)0.5583 (6)0.87825 (13)0.0390 (12)
H26A0.60550.63670.88470.047*
H26B0.56340.48320.90250.047*
C270.5016 (2)0.6826 (6)0.86891 (15)0.0476 (13)
H27A0.49940.75550.89330.057*
H27B0.50530.76990.84700.057*
C280.4383 (2)0.5714 (6)0.85617 (15)0.0498 (13)
H28A0.39880.65550.84890.060*
H28B0.43210.49380.87910.060*
C290.4407 (2)0.4491 (7)0.82035 (15)0.0549 (14)
H29A0.44200.52700.79650.066*
H29B0.39920.37250.81370.066*
C300.5032 (2)0.3236 (6)0.82947 (14)0.0494 (14)
H30A0.49860.23430.85080.059*
H30B0.50510.25260.80480.059*
U11U22U33U12U13U23
Si10.0259 (7)0.0320 (7)0.0262 (6)0.0027 (6)0.0122 (5)0.0036 (6)
C10.032 (3)0.028 (3)0.027 (2)−0.006 (2)0.007 (2)0.0055 (19)
C20.026 (2)0.026 (2)0.022 (2)−0.001 (2)0.0062 (19)0.0042 (19)
C30.028 (2)0.028 (2)0.023 (2)−0.003 (2)0.009 (2)0.0007 (19)
C40.034 (3)0.029 (3)0.025 (2)−0.002 (2)0.009 (2)0.003 (2)
C50.026 (2)0.027 (2)0.020 (2)0.000 (2)0.0050 (18)−0.0040 (19)
C60.024 (2)0.030 (3)0.022 (2)−0.003 (2)0.009 (2)−0.003 (2)
C70.035 (3)0.043 (3)0.029 (3)0.002 (2)0.011 (2)−0.001 (2)
C80.040 (3)0.045 (3)0.033 (3)0.009 (2)0.010 (2)−0.004 (2)
C90.050 (3)0.037 (3)0.038 (3)0.013 (2)0.011 (3)0.004 (2)
C100.042 (3)0.038 (3)0.031 (3)0.001 (2)0.014 (2)0.005 (2)
C110.026 (2)0.027 (3)0.029 (2)0.002 (2)0.009 (2)−0.002 (2)
C120.024 (2)0.032 (3)0.028 (3)0.001 (2)0.007 (2)0.000 (2)
C130.029 (3)0.033 (3)0.028 (2)0.005 (2)0.010 (2)0.004 (2)
C140.051 (3)0.041 (3)0.047 (3)0.000 (2)0.026 (3)−0.005 (2)
C150.071 (4)0.043 (3)0.040 (3)0.002 (3)0.016 (3)−0.009 (2)
C160.061 (3)0.053 (3)0.035 (3)0.010 (3)0.014 (3)−0.007 (3)
C170.067 (4)0.068 (4)0.039 (3)−0.001 (3)0.032 (3)−0.005 (3)
C180.063 (3)0.052 (3)0.027 (2)−0.009 (3)0.025 (2)−0.006 (2)
C190.029 (2)0.031 (3)0.024 (2)0.002 (2)0.011 (2)0.001 (2)
C200.037 (3)0.036 (3)0.031 (3)0.003 (2)0.012 (2)0.002 (2)
C210.030 (3)0.047 (3)0.041 (3)−0.006 (2)0.005 (2)0.002 (2)
C220.029 (3)0.056 (3)0.042 (3)−0.008 (2)0.012 (2)0.004 (2)
C230.042 (3)0.042 (3)0.049 (3)−0.009 (3)0.016 (2)0.002 (3)
C240.032 (3)0.033 (3)0.046 (3)−0.001 (2)0.009 (2)0.009 (2)
C250.029 (3)0.033 (3)0.033 (3)0.002 (2)0.014 (2)0.001 (2)
C260.026 (3)0.035 (3)0.055 (3)0.001 (2)0.008 (2)−0.011 (2)
C270.029 (3)0.040 (3)0.078 (4)0.005 (2)0.020 (3)−0.009 (3)
C280.032 (3)0.051 (3)0.069 (4)0.010 (2)0.016 (3)−0.006 (3)
C290.033 (3)0.064 (4)0.065 (4)0.005 (3)0.006 (3)−0.013 (3)
C300.031 (3)0.053 (3)0.059 (3)0.014 (2)−0.001 (2)−0.019 (3)
Si1—C121.845 (4)C17—H17B0.9900
Si1—C191.880 (4)C18—H18A0.9900
Si1—C131.882 (4)C18—H18B0.9900
Si1—C251.887 (4)C19—C201.525 (5)
C1—C3i1.364 (5)C19—C241.537 (5)
C1—C21.423 (5)C19—H19A1.0000
C1—H1A0.9500C20—C211.519 (5)
C2—C61.395 (5)C20—H20A0.9900
C2—C31.437 (5)C20—H20B0.9900
C3—C1i1.364 (5)C21—C221.516 (5)
C3—C41.465 (5)C21—H21A0.9900
C4—C101.370 (5)C21—H21B0.9900
C4—C51.406 (5)C22—C231.514 (5)
C5—C71.372 (5)C22—H22A0.9900
C5—C61.469 (5)C22—H22B0.9900
C6—C111.411 (5)C23—C241.521 (5)
C7—C81.394 (5)C23—H23A0.9900
C7—H7A0.9500C23—H23B0.9900
C8—C91.370 (5)C24—H24A0.9900
C8—H8A0.9500C24—H24B0.9900
C9—C101.394 (5)C25—C301.521 (5)
C9—H9A0.9500C25—C261.527 (5)
C10—H10A0.9500C25—H25A1.0000
C11—C121.211 (5)C26—C271.530 (5)
C13—C141.528 (5)C26—H26A0.9900
C13—C181.528 (5)C26—H26B0.9900
C13—H13A1.0000C27—C281.492 (6)
C14—C151.522 (5)C27—H27A0.9900
C14—H14A0.9900C27—H27B0.9900
C14—H14B0.9900C28—C291.512 (6)
C15—C161.502 (6)C28—H28A0.9900
C15—H15A0.9900C28—H28B0.9900
C15—H15B0.9900C29—C301.531 (5)
C16—C171.510 (6)C29—H29A0.9900
C16—H16A0.9900C29—H29B0.9900
C16—H16B0.9900C30—H30A0.9900
C17—C181.515 (5)C30—H30B0.9900
C17—H17A0.9900
C12—Si1—C19105.33 (18)H18A—C18—H18B107.9
C12—Si1—C13108.07 (18)C20—C19—C24109.7 (3)
C19—Si1—C13111.14 (18)C20—C19—Si1113.8 (3)
C12—Si1—C25106.13 (18)C24—C19—Si1116.7 (3)
C19—Si1—C25110.79 (18)C20—C19—H19A105.1
C13—Si1—C25114.77 (19)C24—C19—H19A105.1
C3i—C1—C2117.7 (4)Si1—C19—H19A105.1
C3i—C1—H1A121.2C21—C20—C19112.9 (3)
C2—C1—H1A121.2C21—C20—H20A109.0
C6—C2—C1130.3 (4)C19—C20—H20A109.0
C6—C2—C3108.7 (3)C21—C20—H20B109.0
C1—C2—C3121.0 (3)C19—C20—H20B109.0
C1i—C3—C2121.3 (4)H20A—C20—H20B107.8
C1i—C3—C4131.0 (4)C20—C21—C22110.9 (3)
C2—C3—C4107.7 (3)C20—C21—H21A109.5
C10—C4—C5120.0 (4)C22—C21—H21A109.5
C10—C4—C3132.8 (4)C20—C21—H21B109.5
C5—C4—C3107.2 (3)C22—C21—H21B109.5
C7—C5—C4121.1 (4)H21A—C21—H21B108.1
C7—C5—C6130.5 (4)C23—C22—C21111.2 (3)
C4—C5—C6108.3 (3)C23—C22—H22A109.4
C2—C6—C11125.8 (4)C21—C22—H22A109.4
C2—C6—C5108.0 (3)C23—C22—H22B109.4
C11—C6—C5125.9 (3)C21—C22—H22B109.4
C5—C7—C8118.3 (4)H22A—C22—H22B108.0
C5—C7—H7A120.9C22—C23—C24111.5 (4)
C8—C7—H7A120.9C22—C23—H23A109.3
C9—C8—C7120.8 (4)C24—C23—H23A109.3
C9—C8—H8A119.6C22—C23—H23B109.3
C7—C8—H8A119.6C24—C23—H23B109.3
C8—C9—C10121.0 (4)H23A—C23—H23B108.0
C8—C9—H9A119.5C23—C24—C19112.9 (3)
C10—C9—H9A119.5C23—C24—H24A109.0
C4—C10—C9118.8 (4)C19—C24—H24A109.0
C4—C10—H10A120.6C23—C24—H24B109.0
C9—C10—H10A120.6C19—C24—H24B109.0
C12—C11—C6177.3 (4)H24A—C24—H24B107.8
C11—C12—Si1173.1 (4)C30—C25—C26110.1 (3)
C14—C13—C18109.0 (3)C30—C25—Si1113.8 (3)
C14—C13—Si1116.4 (3)C26—C25—Si1111.1 (3)
C18—C13—Si1113.2 (3)C30—C25—H25A107.2
C14—C13—H13A105.8C26—C25—H25A107.2
C18—C13—H13A105.8Si1—C25—H25A107.2
Si1—C13—H13A105.8C25—C26—C27113.2 (4)
C15—C14—C13112.8 (4)C25—C26—H26A108.9
C15—C14—H14A109.0C27—C26—H26A108.9
C13—C14—H14A109.0C25—C26—H26B108.9
C15—C14—H14B109.0C27—C26—H26B108.9
C13—C14—H14B109.0H26A—C26—H26B107.7
H14A—C14—H14B107.8C28—C27—C26111.1 (4)
C16—C15—C14111.7 (4)C28—C27—H27A109.4
C16—C15—H15A109.3C26—C27—H27A109.4
C14—C15—H15A109.3C28—C27—H27B109.4
C16—C15—H15B109.3C26—C27—H27B109.4
C14—C15—H15B109.3H27A—C27—H27B108.0
H15A—C15—H15B107.9C27—C28—C29111.6 (4)
C15—C16—C17110.7 (4)C27—C28—H28A109.3
C15—C16—H16A109.5C29—C28—H28A109.3
C17—C16—H16A109.5C27—C28—H28B109.3
C15—C16—H16B109.5C29—C28—H28B109.3
C17—C16—H16B109.5H28A—C28—H28B108.0
H16A—C16—H16B108.1C28—C29—C30111.2 (4)
C16—C17—C18112.5 (4)C28—C29—H29A109.4
C16—C17—H17A109.1C30—C29—H29A109.4
C18—C17—H17A109.1C28—C29—H29B109.4
C16—C17—H17B109.1C30—C29—H29B109.4
C18—C17—H17B109.1H29A—C29—H29B108.0
H17A—C17—H17B107.8C25—C30—C29112.9 (4)
C17—C18—C13111.8 (4)C25—C30—H30A109.0
C17—C18—H18A109.2C29—C30—H30A109.0
C13—C18—H18A109.2C25—C30—H30B109.0
C17—C18—H18B109.2C29—C30—H30B109.0
C13—C18—H18B109.2H30A—C30—H30B107.8
C3i—C1—C2—C6−179.9 (4)C19—Si1—C13—C18−64.5 (4)
C3i—C1—C2—C3−0.3 (6)C25—Si1—C13—C1862.2 (4)
C6—C2—C3—C1i180.0 (4)C18—C13—C14—C1554.6 (5)
C1—C2—C3—C1i0.3 (6)Si1—C13—C14—C15−175.9 (3)
C6—C2—C3—C40.4 (4)C13—C14—C15—C16−55.5 (5)
C1—C2—C3—C4−179.3 (3)C14—C15—C16—C1753.9 (5)
C1i—C3—C4—C102.0 (8)C15—C16—C17—C18−54.7 (5)
C2—C3—C4—C10−178.5 (4)C16—C17—C18—C1355.9 (5)
C1i—C3—C4—C5−178.5 (4)C14—C13—C18—C17−54.4 (5)
C2—C3—C4—C51.1 (4)Si1—C13—C18—C17174.3 (3)
C10—C4—C5—C7−2.1 (6)C12—Si1—C19—C2069.1 (3)
C3—C4—C5—C7178.3 (4)C13—Si1—C19—C20−47.7 (3)
C10—C4—C5—C6177.6 (4)C25—Si1—C19—C20−176.5 (3)
C3—C4—C5—C6−2.0 (4)C12—Si1—C19—C24−161.5 (3)
C1—C2—C6—C11−7.7 (7)C13—Si1—C19—C2481.7 (3)
C3—C2—C6—C11172.6 (4)C25—Si1—C19—C24−47.1 (3)
C1—C2—C6—C5178.1 (4)C24—C19—C20—C2153.6 (4)
C3—C2—C6—C5−1.6 (4)Si1—C19—C20—C21−173.6 (3)
C7—C5—C6—C2−178.0 (4)C19—C20—C21—C22−56.2 (5)
C4—C5—C6—C22.3 (4)C20—C21—C22—C2356.1 (5)
C7—C5—C6—C117.8 (7)C21—C22—C23—C24−55.3 (5)
C4—C5—C6—C11−171.9 (4)C22—C23—C24—C1954.2 (5)
C4—C5—C7—C81.9 (6)C20—C19—C24—C23−52.4 (5)
C6—C5—C7—C8−177.8 (4)Si1—C19—C24—C23176.3 (3)
C5—C7—C8—C9−0.2 (6)C12—Si1—C25—C30−60.6 (3)
C7—C8—C9—C10−1.4 (7)C19—Si1—C25—C30−174.4 (3)
C5—C4—C10—C90.6 (6)C13—Si1—C25—C3058.7 (4)
C3—C4—C10—C9−179.9 (4)C12—Si1—C25—C2664.3 (3)
C8—C9—C10—C41.1 (7)C19—Si1—C25—C26−49.5 (3)
C2—C6—C11—C12−69 (9)C13—Si1—C25—C26−176.4 (3)
C5—C6—C11—C12104 (9)C30—C25—C26—C27−52.0 (5)
C6—C11—C12—Si175 (10)Si1—C25—C26—C27−179.0 (3)
C19—Si1—C12—C1199 (3)C25—C26—C27—C2854.7 (5)
C13—Si1—C12—C11−142 (3)C26—C27—C28—C29−55.9 (5)
C25—Si1—C12—C11−19 (3)C27—C28—C29—C3056.0 (6)
C12—Si1—C13—C1452.9 (4)C26—C25—C30—C2951.8 (5)
C19—Si1—C13—C14168.0 (3)Si1—C25—C30—C29177.3 (3)
C25—Si1—C13—C14−65.3 (4)C28—C29—C30—C25−54.4 (5)
C12—Si1—C13—C18−179.6 (3)
  3 in total

1.  n-Type organic semiconductors in organic electronics.

Authors:  John E Anthony; Antonio Facchetti; Martin Heeney; Seth R Marder; Xiaowei Zhan
Journal:  Adv Mater       Date:  2010-09-08       Impact factor: 30.849

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Indenofluorenes and derivatives: syntheses and emerging materials applications.

Authors:  Aaron G Fix; Daniel T Chase; Michael M Haley
Journal:  Top Curr Chem       Date:  2014
  3 in total

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