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Volume 69 
Part 3 
Page o368  
March 2013  

Received 6 January 2013
Accepted 4 February 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.098
Data-to-parameter ratio = 12.8
Details
Open access

2-(4-Fluorophenyl)-1-(4-methoxyphenyl)-1H-phenanthro[9,10-d]imidazole

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

In the title compound, C28H19FN2O, the phenanthrene fused with an imidazole ring, constituting an essentially planar tetracyclic system [maximum deviation = 0.032 (2) Å], makes dihedral angles of 60.83 (4) and 80.55 (4)° with the fluorobenzene and methoxybenzene rings, respectively. The dihedral angle between the the methoxybenzene and fluorobenzene rings is 69.45 (6)°. In the crystal, C-H...O hydrogen bonds connect the molecules into infinite strands along the b axis. The crystal structure is further consolidated by C-H...[pi] interactions.

Related literature

For background to the supramolecular architecture of phenanthrene derivatives, see: Krebs & Spanggaard (2002[Krebs, F. C. & Spanggaard, H. (2002). J. Org. Chem. 67, 7185-7192.]); Bian et al. (2002[Bian, Z. Q., Wang, K. Z. & Jin, L. P. (2002). Polyhedron, 21, 313-319.]); Che et al. (2008[Che, G. B., Liu, B., Wang, Q. W. & Xu, Z. L. (2008). CrystEngComm, 10, 184-191.]); Stephenson & Hardie (2006[Stephenson, M. D. & Hardie, M. J. (2006). Cryst. Growth Des. 6, 423-456.]). For the crystal structures of closely related compounds, see: Yuan et al. (2011[Yuan, Y., Li, D., Zhang, X., Liu, Y., Zhang, J. & Wang, Y. (2011). New J. Chem. 35, 1534-1540.]); Krebs et al. (2001[Krebs, F. C., Lindvold, L. R. & Jorgesen, M. (2001). Tetrahedron Lett. 62, 6753-6757.]).

[Scheme 1]

Experimental

Crystal data
  • C28H19FN2O

  • Mr = 418.45

  • Triclinic, [P \overline 1]

  • a = 9.6430 (3) Å

  • b = 9.8980 (3) Å

  • c = 12.3070 (4) Å

  • [alpha] = 77.432 (1)°

  • [beta] = 71.621 (1)°

  • [gamma] = 73.158 (1)°

  • V = 1056.57 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 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 = 0.975, Tmax = 0.983

  • 18612 measured reflections

  • 3723 independent reflections

  • 3183 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.098

  • S = 1.03

  • 3723 reflections

  • 290 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1/C7/N2/C15/C16, C1-C6 and C15-C17/C22/C23/C28 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C21-H21...O1i 0.93 2.59 3.426 (2) 151
C9-H9...Cg1ii 0.93 2.74 3.535 143
C26-H26...Cg2iii 0.93 2.81 3.590 143
C13-H13...Cg3iv 0.93 2.76 3.629 152
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y, -z+1; (iii) x, y+1, z; (iv) -x+2, -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 and XPREP (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: PV2618 ).


Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for his help with the data collection.

References

Bian, Z. Q., Wang, K. Z. & Jin, L. P. (2002). Polyhedron, 21, 313-319.  [ISI] [CSD] [CrossRef] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Che, G. B., Liu, B., Wang, Q. W. & Xu, Z. L. (2008). CrystEngComm, 10, 184-191.  [ISI] [CSD] [CrossRef] [ChemPort]
Krebs, F. C., Lindvold, L. R. & Jorgesen, M. (2001). Tetrahedron Lett. 62, 6753-6757.  [ISI] [CSD] [CrossRef]
Krebs, F. C. & Spanggaard, H. (2002). J. Org. Chem. 67, 7185-7192.  [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stephenson, M. D. & Hardie, M. J. (2006). Cryst. Growth Des. 6, 423-456.  [CSD] [CrossRef] [ChemPort]
Yuan, Y., Li, D., Zhang, X., Liu, Y., Zhang, J. & Wang, Y. (2011). New J. Chem. 35, 1534-1540.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o368  [ doi:10.1107/S1600536813003504 ]

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