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Volume 65 
Part 4 
Page o927  
April 2009  

Received 25 March 2009
Accepted 26 March 2009
Online 31 March 2009

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Key indicators
Single-crystal X-ray study
T = 103 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.125
Data-to-parameter ratio = 21.5
Details
Open access

8-(Biphenyl-2-yl)-7,9-diphenyl-8H-cyclopenta[a]acenaphthylen-8-ol

Peter G. Jones,a* Marc Debeaux,b Henning Hopf,c Wolfgang Kowalskyb and Hans-Hermann Johannesb

aInstitut für Anorganische und Analytische Chemie, Technical University of Braunschweig, Postfach 3329, 38023 Braunschweig, Germany,bLabor für Elektrooptik am Institut für Hochfrequenztechnik, Technical University of Braunschweig, Postfach 3329, 38023 Braunschweig, Germany, and cInstitut für Organische Chemie, Technical University of Braunschweig, Postfach 3329, 38023 Braunschweig, Germany
Correspondence e-mail: p.jones@tu-bs.de

In the title compound, C39H26O, the cyclopenta[a]acenaphthylene skeleton displays the expected distortions, with formal sp2 bond angles as high as C-C-C = 142.50 (10)°. The OH group forms intermolecular hydrogen bonds via x-axis translation to the centroid (Cg) of the pendant phenyl ring of the biphenyl system, with H...Cg = 2.41 Å and O-H...Cg = 153°.

Related literature

For related literature, see: Saragi et al. (2007[Saragi, T. P. I., Spehr, T., Siebert, A., Fuhrmann-Lieker, T. & Salbeck, J. (2007). Chem. Rev. 107, 1011-1065.]); Velusamy et al. (2007[Velusamy, M., Thomas, K. R. J., Chen, C.-H., Lin, J. T., Wen, Y. S., Hsieh, W.-T., Lai, C.-H. & Chou, P.-T. (2007). Dalton Trans. pp. 3025-3034.]).

[Scheme 1]

Experimental

Crystal data

  • C39H26O

  • Mr = 510.60

  • Monoclinic, P 21 /n

  • a = 7.3837 (4) Å

  • b = 18.4001 (12) Å

  • c = 19.2505 (12) Å

  • [beta] = 97.549 (3)°

  • V = 2592.7 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 103 K

  • 0.35 × 0.20 × 0.20 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.893, Tmax = 0.985

  • 53233 measured reflections

  • 7857 independent reflections

  • 6335 reflections with I > 2[sigma](I)

  • Rint = 0.036
Refinement

  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.125

  • S = 1.02

  • 7857 reflections

  • 365 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: XP (Siemens, 1994[Siemens (1994). XP. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2916 ).

Acknowledgements

The authors thank the Bundesministerium für Bildung und Forschung (BMBF 01 BD 0687) for financial support.

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Saragi, T. P. I., Spehr, T., Siebert, A., Fuhrmann-Lieker, T. & Salbeck, J. (2007). Chem. Rev. 107, 1011-1065.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens (1994). XP. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Velusamy, M., Thomas, K. R. J., Chen, C.-H., Lin, J. T., Wen, Y. S., Hsieh, W.-T., Lai, C.-H. & Chou, P.-T. (2007). Dalton Trans. pp. 3025-3034.  [CSD] [CrossRef]

Acta Cryst (2009). E65, o927  [ doi:10.1107/S1600536809011222 ]

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