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Volume 64 
Part 11 
Page o2183  
November 2008  

Received 27 September 2008
Accepted 20 October 2008
Online 25 October 2008

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.056
wR = 0.146
Data-to-parameter ratio = 6.4
Details
Open access

5,5-Bis(4-methoxyphenyl)-2,8-bis[3-(trifluoromethyl)phenyl]-5H-cyclopenta[2,1-b:3,4-b']dipyridine

aDepartment of Materials Science and Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan, and bInstitute for Molecular Science, Myodaiji, Okazaki 444-8585, Japan
Correspondence e-mail: ono.katsuhiko@nitech.ac.jp

The title compound, C39H26F6N2O2, showed two melting transitions 477.4 and 506.5 K in a differential scanning calorimetry (DSC) study. The first of these can be attributed to a melting phase transition arising from the rotation of two trifluoromethyl groups. In the crystal structure, both trifluoromethyl groups are disordered over two sites with occupancy factors of 0.660 (17) and 0.340 (17) for the major and minor orientations, respectively. The introduction of trifluoromethyl groups inhibits [pi]-stacking between the diazafluorene (cyclopenta[2,1-b:3,4-b']dipyridine) units. Three short F...O contacts between 2.80 (3) and 2.95 (1) Å are observed in the crystal structure.

Related literature

The synthesis and thermal properties of the title compound were reported by Ono et al. (2007[Ono, K., Nagano, K., Suto, M. & Saito, K. (2007). Heterocycles, 71, 799-804.]). For related literature on molecular and crystal structures, including the 4,5-diazafluorene system, see: Ono & Saito (2008[Ono, K. & Saito, K. (2008). Heterocycles, 75, 2381-2413.]).

[Scheme 1]

Experimental

Crystal data
  • C39H26F6N2O2

  • Mr = 668.62

  • Orthorhombic, P 21 21 21

  • a = 9.283 (2) Å

  • b = 12.357 (3) Å

  • c = 26.941 (6) Å

  • V = 3090.4 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 173 (1) K

  • 0.38 × 0.30 × 0.20 mm

Data collection
  • Rigaku/MSC Mercury CCD diffractometer

  • Absorption correction: none

  • 20599 measured reflections

  • 3171 independent reflections

  • 2849 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.146

  • S = 1.05

  • 3171 reflections

  • 498 parameters

  • 24 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Data collection: CrystalClear (Rigaku/MSC, 2001[Rigaku/MSC (2001). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2809 ).


Acknowledgements

This work was supported by a Grant-in-Aid for Scientific Research (grant No. 19550034) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. The authors thank the Instrument Center of the Institute for Molecular Science for the X-ray structure analysis.

References

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Ono, K., Nagano, K., Suto, M. & Saito, K. (2007). Heterocycles, 71, 799-804.  [ChemPort]
Ono, K. & Saito, K. (2008). Heterocycles, 75, 2381-2413.  [ChemPort]
Rigaku/MSC (2001). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2008). E64, o2183  [ doi:10.1107/S160053680803420X ]

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