4,7-Diphenyl-2,9-bis­(trichloro­meth­yl)-1,10-phenanthroline

Xie, M.-H.; Liu, Y.-L.; Zou, P.; He, Y.-J.; Huang, B.

doi:10.1107/S1600536809051071

Volume 66
Part 1
Page o5
January 2010

Received 17 November 2009
Accepted 26 November 2009
Online 4 December 2009

Key indicators
Single-crystal X-ray study
T = 133 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.033
wR = 0.080
Data-to-parameter ratio = 16.3
Details

4,7-Diphenyl-2,9-bis(trichloromethyl)-1,10-phenanthroline

Min-Hao Xie,^a Ya-Ling Liu,^a Pei Zou,^a Yong-Jun He ^a and Biao Huang ^a ^*

^aJiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China
Correspondence e-mail: xiemh0704@sina.com

In the title compound, C₂₆H₁₄Cl₆N₂, the phenanthroline ring system is essentially planar, with an r.m.s. deviation of 0.048 (6) Å, and makes dihedral angles of 64.8 (14) and 66.6 (6)° with the two terminal phenyl rings. One of the trichloromethyl groups is disordered over two positions, with occupancies of 0.42 (2) and 0.58 (2).

Related literature

For 4,7-bis(chlorosulfophenyl)-1,10-phenanthroline-2,9-dicarboxylic acid, see: Evangelista et al. (1988); Papanastasiou-Diamandi et al. (1989); Scorilas & Diamandis (2000). For a related structure, see: Wang et al. (2007).

Experimental

Crystal data

C₂₆H₁₄Cl₆N₂
M_r = 567.09
Monoclinic, P 2₁ /c
a = 11.253 (2) Å
b = 19.789 (4) Å
c = 11.299 (2) Å
= 106.544 (3)°
V = 2411.9 (8) Å³
Z = 4
Mo K radiation
= 0.73 mm^-1
T = 133 K
0.30 × 0.27 × 0.20 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: multi-scan (ABSCOR, Higashi, 1995) T_min = 0.810, T_max = 0.867
19334 measured reflections
5453 independent reflections
4573 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.080
S = 1.00
5453 reflections
335 parameters
6 restraints
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.31 e Å^-3

Data collection: RAPID-AUTO (Rigaku 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2495 ).

Acknowledgements

We acknowledge financial support by the National 863 Plan Foundation of China (grant No. 2008 A A10Z415), the Social Development Foundation of Jiangsu (grant No. BE2008633) and the Medical Research Project of Jiangsu (grant No. H200736).

References

Evangelista, R. A., Pollak, A., Allore, B., Templeton, E. F. & Morton, R. C. (1988). Clin. Biochem. 21, 173-178.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Papanastasiou-Diamandi, A., Conway, K. & Diamandis, E. P. (1989). J. Pharm. Sci. 78, 617-621.
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Scorilas, A. & Diamandis, E. P. (2000). Clin. Biochem. 33, 345-350.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, J., Ye, J.-W. & Wang, Y. (2007). Acta Cryst. E63, o2007-o2008.

organic compounds