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Volume 69 
Part 6 
Page o890  
June 2013  

Received 25 February 2013
Accepted 3 May 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.006 Å
R = 0.076
wR = 0.151
Data-to-parameter ratio = 15.2
Details
Open access

6,12-Bis[(tricyclohexylsilyl)ethynyl]indeno[1,2-b]fluorene

aDepartment of Chemistry and Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, USA, and bCAMCOR, University of Oregon, 1443 East 13th Avenue, Eugene, Oregon 97403, USA
Correspondence e-mail: haley@uoregon.edu

The title compound, C60H76Si2, a formally anti-aromatic system containing 20-[pi] 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 sp2 carbon contact of 3.283 (6) Å, less than the sum of the van der Waals radii. The center of the molecule sits on an inversion center.

Related literature

For the synthetic procedure, see: Kendrick et al. (2012[Kendrick, M. J., Neunzert, A., Payne, M. M., Purushothaman, B., Rose, B. D., Anthony, J. E., Haley, M. M. & Ostroverkhova, O. (2012). J. Phys. Chem. C, 116, 18108-18116.]). For information about the indenofluorene molecular framework, see: Fix et al. (2012[Fix, A. G., Chase, D. T. & Haley, M. M. (2012). Top. Curr. Chem. doi:10.1007/128_2012_376. ]) and about crystal packing, see: Anthony et al. (2010[Anthony, J. E., Fachetti, A., Heeney, M., Marder, S. R. & Zhan, X. (2010). Adv. Mater. 22, 3876-3892.]).

[Scheme 1]

Experimental

Crystal data
  • C60H76Si2

  • Mr = 853.39

  • Monoclinic, C 2/c

  • a = 20.219 (7) Å

  • b = 7.246 (2) Å

  • c = 33.885 (11) Å

  • [beta] = 103.017 (7)°

  • V = 4837 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.991, Tmax = 0.999

  • 22528 measured reflections

  • 4268 independent reflections

  • 2181 reflections with I > 2[sigma](I)

  • Rint = 0.176

Refinement
  • R[F2 > 2[sigma](F2)] = 0.076

  • wR(F2) = 0.151

  • S = 1.01

  • 4268 reflections

  • 280 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: XS in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: XL in SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2470 ).


Acknowledgements

The authors thank the National Science Foundation (CHE-1013032) for financial support. BDR acknowledges the American Chemical Society Division of Organic Chemistry for the 2012-2013 Troyanski Fellowship.

References

Anthony, J. E., Fachetti, A., Heeney, M., Marder, S. R. & Zhan, X. (2010). Adv. Mater. 22, 3876-3892.  [ISI] [CrossRef] [ChemPort] [PubMed]
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fix, A. G., Chase, D. T. & Haley, M. M. (2012). Top. Curr. Chem. doi:10.1007/128_2012_376.
Kendrick, M. J., Neunzert, A., Payne, M. M., Purushothaman, B., Rose, B. D., Anthony, J. E., Haley, M. M. & Ostroverkhova, O. (2012). J. Phys. Chem. C, 116, 18108-18116.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o890  [ doi:10.1107/S160053681301218X ]

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