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Volume 69 
Part 8 
Pages o1293-o1294  
August 2013  

Received 6 June 2013
Accepted 13 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.124
Data-to-parameter ratio = 16.2
Details
Open access

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

aShri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli 621 105, India,bDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram, India,cDepartment of Chemistry, Urumudhanalakshmi College, Tiruchirappalli 620 019, India, and dDepartment of Physics, Urumudhanalakshmi College, Tiruchirappalli 620 019, India
Correspondence e-mail: sakthi2udc@gmail.com

In the title compound, C29H19F3N2O, a phenanthroline-fused imidazole tetracyclic system, the fused benzene rings deviate slightly from the central ring and make dihedral angles with this ring of 3.47 (8) and 3.05 (8)°. The trifluoromethylphenyl ring is roughly coplanar with the phenanthroline-fused imidazole tetracyclic system [dihedral angle = 11.02 (6)°], while the methoxyphenyl ring is almost perpendicular [dihedral angle = 87.65 (6)°]. There are intramolecular C-H ...[pi] interactions involving the methoxyphenyl ring and the central phenanthroline ring, as well as an intermolecular C-H...[pi] interaction involving the phenanthroline ring. In addition, there is an intermolecular [pi]-[pi] interaction involving the central phenanthroline ring and the trifluoromethylphenyl ring [centroid-centroid distance = 3.685 (2) Å], as well as C-H...N interactions linking the molecules into dimers.

Related literature

For background to the supramolecular architecture of phenanthroline compounds, see: Lehn (1995[Lehn, J. M. (1995). In Supramolecular Chemistry, Concept of Perspectives. Weinheim: VCH.]). For metal sensors, see: Walters et al. (2000[Walters, K. A., Trouillrt, L., Guillerez, S. & Schanze, K. S. (2000). Inorg. Chem. 39, 5496-5509.]). For molecular electronics, see: Peng et al. (1997[Peng, Z., Gharavi, A. R. & Yu, L. J. (1997). J. Am. Chem. Soc. 119, 4622-4632.]). For photo sensitizers see: Hara et al. (2001[Hara, K., Sugihara, H., Tachibana, Y., Islam, A., Yanagida, M., Sayama, K. & Arakawa, H. (2001). Langmuir, 17, 5992-5999.]). For a related structure, see: Sathishkumar et al. (2013[Sathishkumar, R., Mohandas, T., Sakthivel, P. & Jayabharathi, J. (2013). Acta Cryst. E69, o367.]).

[Scheme 1]

.

Experimental

Crystal data
  • C29H19F3N2O

  • Mr = 468.46

  • Monoclinic, P 21 /c

  • a = 11.7063 (9) Å

  • b = 20.2301 (16) Å

  • c = 9.5419 (8) Å

  • [beta] = 99.725 (2)°

  • V = 2227.2 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 173 K

  • 0.32 × 0.29 × 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 = 0.956, Tmax = 0.999

  • 24449 measured reflections

  • 5128 independent reflections

  • 3511 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.124

  • S = 1.01

  • 5128 reflections

  • 317 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg are the centroids of the methoxyphenyl and phenthroline rings, repsectively.

D-H...A D-H H...A D...A D-H...A
C28-H28...N2i 0.95 2.55 3.402 (2) 150
C3-H3...Cg1 0.95 2.86 3.719 (2) 154
C10-H10...Cg2ii 0.95 2.69 3.419 (2) 136
C17-H17...Cg1 0.95 2.74 3.6042 (2) 154
Symmetry codes: (i) -x+1, -y, -z+2; (ii) [x, -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 (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: BV2223 ).


Acknowledgements

The authors thank Dr Babu Varghese, Senior Scientific Officer SAIF, IIT Chennai, India, for carrying out the data collection.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hara, K., Sugihara, H., Tachibana, Y., Islam, A., Yanagida, M., Sayama, K. & Arakawa, H. (2001). Langmuir, 17, 5992-5999.  [Web of Science] [CrossRef] [ChemPort]
Lehn, J. M. (1995). In Supramolecular Chemistry, Concept of Perspectives. Weinheim: VCH.
Peng, Z., Gharavi, A. R. & Yu, L. J. (1997). J. Am. Chem. Soc. 119, 4622-4632.  [CrossRef] [ChemPort] [Web of Science]
Sathishkumar, R., Mohandas, T., Sakthivel, P. & Jayabharathi, J. (2013). Acta Cryst. E69, o367.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Walters, K. A., Trouillrt, L., Guillerez, S. & Schanze, K. S. (2000). Inorg. Chem. 39, 5496-5509.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1293-o1294   [ doi:10.1107/S1600536813019351 ]

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