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Volume 69 
Part 5 
Page o710  
May 2013  

Received 29 March 2013
Accepted 7 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.068
wR = 0.236
Data-to-parameter ratio = 72.7
Details
Open access

1-(4-Methylphenyl)-2-[4-(trifluoromethyl)phenyl]-1H-phenanthro[9,10-d]imidazole

aDepartment of Physics, Shri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli 621 105, India,bAnnamalai University, Annamalainagar, Chidambaram, India,cDepartment of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli, Tamilnadu, India, and dDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli, Tamilnadu, India
Correspondence e-mail: sakthi2udc@gmail.com

In the title compound, C29H19F3N2, the tetracyclic ring system is essentially planar [maximum deviation from the best plane = 0.076 (1) Å] and makes dihedral angles of 78.10 (5) and 33.71 (4)° with the methylphenyl and fluorophenyl rings, respectively. An intramolecular C-H...[pi] interaction occurs. In the crystal, pairs of C-H...[pi] interactions link inversion-related molecules.

Related literature

For background to organic electroluminescent materials and devices, see: Adachi et al. (1995[Adachi, C., Nagai, K. & Tamoto, N. (1995). Appl. Phys. Lett. 66, 2679-2681.]); Loy et al. (2002[Loy, D. E., Koene, B. E. & Thompson, M. E. (2002). Adv. Funct. Mater. 12, 245-249.]) and for the photophysical, electrochemical and mobility properties of phenanthroimidazole derivatives, see: Yuan et al. (2011[Yuan, Y., Li, D., Zhang, X., Zhao, X., Liu, Y., Zhang, J. & Wang, Y. (2011). New J. Chem. 35, 1534-1540.]). For applications of imidazole and phenanthrolene derivatives, see: Moylan et al. (1993[Moylan, C. R., Miller, R. D., Twieg, R. J., Betterton, K. M., Lee, V. Y., Matray, T. J. & Nguyen, C. (1993). Chem. Mater. 5, 1499-1508.]); Bu et al. (1996[Bu, X. R., Li, H., Derveer, D. V. & Mintz, E. A. (1996). Tetrahedron Lett. 37, 7331-7334.]); Wang et al. (2002[Wang, S., Zhao, L., Xu, Z., Wu, C. & Cheng, S. (2002). Mater. Lett. 56, 1035-1038.]).

[Scheme 1]

Experimental

Crystal data
  • C29H19F3N2

  • Mr = 452.46

  • Triclinic, [P \overline 1]

  • a = 8.113 (3) Å

  • b = 11.733 (5) Å

  • c = 12.713 (2) Å

  • [alpha] = 76.397 (1)°

  • [beta] = 73.490 (2)°

  • [gamma] = 86.185 (5)°

  • V = 1127.7 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.967, Tmax = 0.977

  • 22540 measured reflections

  • 22540 independent reflections

  • 14735 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.236

  • S = 1.04

  • 22540 reflections

  • 310 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.72 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C15-C20 and C8-C13 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C12-H12...Cg1 0.93 2.84 3.698 (2) 155
C26-H26...Cg2i 0.93 2.86 3.487 (2) 125
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2008[Bruker (2008). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2084 ).


Acknowledgements

PS and AP thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the data collection.

References

Adachi, C., Nagai, K. & Tamoto, N. (1995). Appl. Phys. Lett. 66, 2679-2681.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bu, X. R., Li, H., Derveer, D. V. & Mintz, E. A. (1996). Tetrahedron Lett. 37, 7331-7334.  [CrossRef] [ChemPort] [ISI]
Loy, D. E., Koene, B. E. & Thompson, M. E. (2002). Adv. Funct. Mater. 12, 245-249.  [CrossRef] [ChemPort]
Moylan, C. R., Miller, R. D., Twieg, R. J., Betterton, K. M., Lee, V. Y., Matray, T. J. & Nguyen, C. (1993). Chem. Mater. 5, 1499-1508.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Wang, S., Zhao, L., Xu, Z., Wu, C. & Cheng, S. (2002). Mater. Lett. 56, 1035-1038.  [CrossRef] [ChemPort]
Yuan, Y., Li, D., Zhang, X., Zhao, X., Liu, Y., Zhang, J. & Wang, Y. (2011). New J. Chem. 35, 1534-1540.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o710  [ doi:10.1107/S1600536813009471 ]

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