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Volume 69 
Part 3 
Page o367  
March 2013  

Received 4 January 2013
Accepted 4 February 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.109
Data-to-parameter ratio = 12.9
Details
Open access

1-(3,5-Dimethylphenyl)-2-(4-fluorophenyl)-1H-phenanthro[9,10-d]imidazole

aDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, India,bShri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli 621 105, India, and cDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India
Correspondence e-mail: sakthi2udc@gmail.com

In the title compound, C29H21FN2, the phenanthro tricyclic ring system is essentially planar with a maximum deviation of 0.030 (2) Å and makes dihedral angles between of 77.96 (6) and 37.18 (7)° with the dimethylphenyl and fluorophenyl rings, respectively. The crystal packing features weak C-H...[pi] interactions involving the dimethylphenyl and other phenyl rings.

Related literature

For the use of phenanthroline derivatives in the construction of molecular devices, see: Yamada et al. (1992[Yamada, M., Tanaka, Y., Yoshimoto, T., Kuroda, S. & Shimao, I. (1992). Bull. Chem. Soc. Jpn, 65, 1006-1011.]). For the biological activity of imidazole, see: Nebert & Gonzalez (1987[Nebert, D. W. & Gonzalez, F. J. (1987). Annu Rev. Biochem. 56, 945-993.]). For related metallo-supramolecular chemistry, see: Lehn (1996[Lehn, J. M. (1996). In Supramolecular Chemistry: Concepts and Perspectives. Weinheim: Wiley-VCH Verlag GmbH.]). For applications of complexes based on phenanthroline, see: Walters et al. (2000[Walters, K. A., Trouillet, L., Guillerez, S. & Schanze, K. S. (2000). Inorg. Chem. 39, 5496-5509.]); Peng et al. (1997[Peng, Z., Gharavi, A. R. & Yu, L. J. (1997). J. Am. Chem. Soc. 119, 4622-4632.]); Hara et al. (2001[Hara, K., Sugihara, H., Tachibana, Y., Islam, A., Yanagida, M., Sayama, K., Arakawa, H., Fujihashi, G., Horiguchi, T. & Kinoshita, T. (2001). Langmuir, 17, 5992-5999.]).

[Scheme 1]

Experimental

Crystal data
  • C29H21FN2

  • Mr = 416.48

  • Monoclinic, P 21 /n

  • a = 8.5680 (2) Å

  • b = 10.6070 (3) Å

  • c = 23.6900 (6) Å

  • [beta] = 93.899 (1)°

  • V = 2147.98 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 295 K

  • 0.30 × 0.20 × 0.20 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 = 0.952, Tmax = 0.995

  • 19934 measured reflections

  • 3777 independent reflections

  • 2957 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.109

  • S = 1.02

  • 3777 reflections

  • 292 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C7/C8/C13/C14/C19/C20 and C8-C13 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C9-H9...Cg1 0.93 2.97 3.84 156
C6-H6...Cg2i 0.93 2.97 3.70 155
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2393 ).


References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hara, K., Sugihara, H., Tachibana, Y., Islam, A., Yanagida, M., Sayama, K., Arakawa, H., Fujihashi, G., Horiguchi, T. & Kinoshita, T. (2001). Langmuir, 17, 5992-5999.  [ISI] [CrossRef] [ChemPort]
Lehn, J. M. (1996). In Supramolecular Chemistry: Concepts and Perspectives. Weinheim: Wiley-VCH Verlag GmbH.
Nebert, D. W. & Gonzalez, F. J. (1987). Annu Rev. Biochem. 56, 945-993.  [CrossRef] [ChemPort] [PubMed]
Peng, Z., Gharavi, A. R. & Yu, L. J. (1997). J. Am. Chem. Soc. 119, 4622-4632.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Walters, K. A., Trouillet, L., Guillerez, S. & Schanze, K. S. (2000). Inorg. Chem. 39, 5496-5509.  [ISI] [CrossRef] [PubMed] [ChemPort]
Yamada, M., Tanaka, Y., Yoshimoto, T., Kuroda, S. & Shimao, I. (1992). Bull. Chem. Soc. Jpn, 65, 1006-1011.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2013). E69, o367  [ doi:10.1107/S1600536813003486 ]

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