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

Ono, K.; Tomura, M.; Saito, K.

doi:10.1107/S160053680803420X

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 (C-C) = 0.006 Å
Disorder in main residue
R = 0.056
wR = 0.146
Data-to-parameter ratio = 6.4
Details

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

Katsuhiko Ono,^a ^* Masaaki Tomura ^b and Katsuhiro Saito ^a

^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 FO 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). For related literature on molecular and crystal structures, including the 4,5-diazafluorene system, see: Ono & Saito (2008).

Experimental

Crystal data

C₃₉H₂₆F₆N₂O₂
M_r = 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 radiation
= 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(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.146
S = 1.05
3171 reflections
498 parameters
24 restraints
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.25 e Å^-3

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

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.
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.
Ono, K., Nagano, K., Suto, M. & Saito, K. (2007). Heterocycles, 71, 799-804.
Ono, K. & Saito, K. (2008). Heterocycles, 75, 2381-2413.
Rigaku/MSC (2001). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds