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

Sathishkumar, R.; Mohandas, T.; Sakthivel, P.; Jayabharathi, J.

doi:10.1107/S1600536813003486

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 (C-C) = 0.002 Å
R = 0.039
wR = 0.109
Data-to-parameter ratio = 12.9
Details

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

R. Sathishkumar,^a T. Mohandas,^b P. Sakthivel ^c ^* and J. Jayabharathi ^a

^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). For the biological activity of imidazole, see: Nebert & Gonzalez (1987). For related metallo-supramolecular chemistry, see: Lehn (1996). For applications of complexes based on phenanthroline, see: Walters et al. (2000); Peng et al. (1997); Hara et al. (2001).

Experimental

Crystal data

C₂₉H₂₁FN₂
M_r = 416.48
Monoclinic, P 2₁ /n
a = 8.5680 (2) Å
b = 10.6070 (3) Å
c = 23.6900 (6) Å
= 93.899 (1)°
V = 2147.98 (10) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.952, T_max = 0.995
19934 measured reflections
3777 independent reflections
2957 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.109
S = 1.02
3777 reflections
292 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C9-H9Cg1	0.93	2.97	3.84	156
C6-H6Cg2ⁱ	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); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

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.
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.
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.
Peng, Z., Gharavi, A. R. & Yu, L. J. (1997). J. Am. Chem. Soc. 119, 4622-4632.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Walters, K. A., Trouillet, L., Guillerez, S. & Schanze, K. S. (2000). Inorg. Chem. 39, 5496-5509.
Yamada, M., Tanaka, Y., Yoshimoto, T., Kuroda, S. & Shimao, I. (1992). Bull. Chem. Soc. Jpn, 65, 1006-1011.

organic compounds