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Volume 69 
Part 10 
Pages o1514-o1515  
October 2013  

Received 18 July 2013
Accepted 27 August 2013
Online 7 September 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.109
Data-to-parameter ratio = 16.3
Details
Open access

3,3''-Bis(9-hydroxyfluoren-9-yl)-1,1':3',1''-terphenyl

aDepartment of Chemistry, University of Ioannina, GR-451 10 Ioannina, Greece, and bInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
Correspondence e-mail: edwin.weber@chemie.tu-freiberg.de

The asymmetric unit of the title compound, C44H30O2, contains two independent molecules in which the terminal rings of the terphenyl element are inclined at angles of 36.3 (1) and 22.5 (1)° with respect to the central ring and the dihedral angles between the fluorenyl units are 72.3 (1) and 62.8 (1)°. In the crystal, pairs of O-H...O hydrogen bonds link the molecules into inversion dimers. The hydroxy H atoms not involved in these hydrogen bonds form O-H...[pi] interactions in which the central terphenyl rings act as acceptors. Weak C-H...O contacts and [pi]-[pi] [centroid-centroid distance = 4.088 (2) Å] stacking interactions also occur. Taking into account directed non-covalent bonding between the molecules, the crystal is constructed of supramolecular strands extending along the a-axis direction.

Related literature

For the preparation of the starting material for the synthesis of the title compound, see: Staab & Binnig (1967[Staab, H. A. & Binnig, A. (1967). Chem. Ber. 11, 293-305.]). For background to organic solid-state inclusion chemistry, see: Atwood et al. (1991[Atwood, J. L., Davies, J. E. D. & MacNicol, D. D. (1991). Editors. Inclusion Compounds, Vol. 4. Oxford Universty Press.]). For the design strategy of host compounds, see: Desiraju (1996[Desiraju, G. R. (1996). Comprehensive Supramolecular Chemistry, edited by D. D. MacNicol, F. Toda & R. Bishop, pp. 1-22. Oxford: Elsevier.]). For diol host inclusion complexes, see: Toda (1996[Toda, F. (1996). Comprehensive Supramolecular Chemistry edited by D. D. MacNicol, F. Toda & R. Bishop, pp. 465-516. Oxford: Elsevier.]). For host compound 2,2'-bis(9-hydroxy-9-fluorenyl)biphenyl, see: Weber et al. (1993[Weber, E., Skobridis, K., Wierig, A., Stathi, S., Nassimbeni, L. R. & Niven, M. L. (1993). Angew. Chem. Int. Ed. 32, 606-608.]); Skobridis, Paraskevopoulos et al. (2011[Skobridis, K., Paraskevopoulos, G., Theodorou, V., Seichter, W. & Weber, E. (2011). Cryst. Growth Des. 11, 5275-5288.]); Skobridis, Theodorou et al. (2011[Skobridis, K., Theodorou, V., Seichter, W. & Weber, E. (2011). Cryst. Growth Des. 10, 862-869.]). For weak O-H...[pi] and C-H...O interactions, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, ch. 2. Oxford University Press.]). For [pi]-[pi] stacking interactions, see: James (2004[James, S. L. (2004). Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 1093-1099. Boca Raton: CRC Press.]).

[Scheme 1]

Experimental

Crystal data
  • C44H30O2

  • Mr = 590.68

  • Triclinic, [P \overline 1]

  • a = 11.2292 (3) Å

  • b = 12.4823 (3) Å

  • c = 24.4440 (5) Å

  • [alpha] = 76.070 (1)°

  • [beta] = 78.080 (1)°

  • [gamma] = 66.917 (1)°

  • V = 3034.99 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 150 K

  • 0.32 × 0.18 × 0.06 mm

Data collection
  • Bruker X8 APEXII CCD diffractometer

  • 55787 measured reflections

  • 13774 independent reflections

  • 9930 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.109

  • S = 1.03

  • 13774 reflections

  • 845 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C20-C25 and C20A-C25A rings, respectively.

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.86 (1) 2.07 (1) 2.894 (2) 163 (1)
O2-H2...Cg1ii 0.84 (1) 3.42 (1) 4.163 (2) 150 (1)
O1A-H1A...O2Aiii 0.85 (1) 1.99 (1) 2.807 (2) 160 (1)
O2A-H2A...Cg2iv 0.85 (2) 3.46 (1) 4.169 (2) 145 (1)
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x, -y+2, -z+2; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2410 ).


Acknowledgements

We thank the NMR Center and Mass Spectrometry Unit of the University of Ioannina for measuring the 1H NMR and HRMS spectra. KS thanks the State Scholarships Foundation (IKY) for supporting this work.

References

Atwood, J. L., Davies, J. E. D. & MacNicol, D. D. (1991). Editors. Inclusion Compounds, Vol. 4. Oxford Universty Press.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. (1996). Comprehensive Supramolecular Chemistry, edited by D. D. MacNicol, F. Toda & R. Bishop, pp. 1-22. Oxford: Elsevier.
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, ch. 2. Oxford University Press.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
James, S. L. (2004). Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 1093-1099. Boca Raton: CRC Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Skobridis, K., Paraskevopoulos, G., Theodorou, V., Seichter, W. & Weber, E. (2011). Cryst. Growth Des. 11, 5275-5288.  [CSD] [CrossRef] [ChemPort]
Skobridis, K., Theodorou, V., Seichter, W. & Weber, E. (2011). Cryst. Growth Des. 10, 862-869.  [CrossRef]
Staab, H. A. & Binnig, A. (1967). Chem. Ber. 11, 293-305.  [CrossRef]
Toda, F. (1996). Comprehensive Supramolecular Chemistry edited by D. D. MacNicol, F. Toda & R. Bishop, pp. 465-516. Oxford: Elsevier.
Weber, E., Skobridis, K., Wierig, A., Stathi, S., Nassimbeni, L. R. & Niven, M. L. (1993). Angew. Chem. Int. Ed. 32, 606-608.


Acta Cryst (2013). E69, o1514-o1515   [ doi:10.1107/S1600536813024033 ]

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