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

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

doi:10.1107/S1600536813003504

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 (C-C) = 0.002 Å
R = 0.035
wR = 0.098
Data-to-parameter ratio = 12.8
Details

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

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

^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-HO 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); Bian et al. (2002); Che et al. (2008); Stephenson & Hardie (2006). For the crystal structures of closely related compounds, see: Yuan et al. (2011); Krebs et al. (2001).

Experimental

Crystal data

C₂₈H₁₉FN₂O
M_r = 418.45
Triclinic, $[P \overline 1]$
a = 9.6430 (3) Å
b = 9.8980 (3) Å
c = 12.3070 (4) Å
= 77.432 (1)°
= 71.621 (1)°
= 73.158 (1)°
V = 1056.57 (6) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.975, T_max = 0.983
18612 measured reflections
3723 independent reflections
3183 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.098
S = 1.03
3723 reflections
290 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C21-H21O1ⁱ	0.93	2.59	3.426 (2)	151
C9-H9Cg1ⁱⁱ	0.93	2.74	3.535	143
C26-H26Cg2ⁱⁱⁱ	0.93	2.81	3.590	143
C13-H13Cg3^iv	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); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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.
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.
Krebs, F. C., Lindvold, L. R. & Jorgesen, M. (2001). Tetrahedron Lett. 62, 6753-6757.
Krebs, F. C. & Spanggaard, H. (2002). J. Org. Chem. 67, 7185-7192.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stephenson, M. D. & Hardie, M. J. (2006). Cryst. Growth Des. 6, 423-456.
Yuan, Y., Li, D., Zhang, X., Liu, Y., Zhang, J. & Wang, Y. (2011). New J. Chem. 35, 1534-1540.

organic compounds