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Volume 65 
Part 4 
Page o932  
April 2009  

Received 13 March 2009
Accepted 24 March 2009
Online 1 April 2009

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.181
Data-to-parameter ratio = 16.9
Details
Open access

2-(2,4,6-Trimethylphenyl)-1,10-phenanthroline

Yuxin Zhao,a Yongping Zhang,a* Peiju Yangb and Biao Wub

aState Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China, and bState Key Laboratory for Oxo Synthesis & Selective Oxidation, Lanzhou Institute of Chemical Physics, CAS, Lanzhou 730000, People's Republic of China
Correspondence e-mail: zhangyongp@lzu.edu.cn

In the title molecule, C21H18N2, the mean plane of the benzene ring of the mesityl group forms a dihedral angle of 82.69 (4)° with that of the phenanthroline ring system. The crystal structure is stabilized by [pi]-[pi] stacking interactions between the phenanthroline system and the benzene ring of the mesityl group of a symmetry-related molecule, with centroid-centroid distances of 3.7776 (14) and 3.7155 (13) Å.

Related literature

For background information on phenanthroline derivatives, see: Schmittel et al. (2001[Schmittel, M., Michel, C., Liu, S.-X., Schildbach, D. & Fenske, D. (2001). Eur. J. Inorg. Chem. pp. 1155-1166.]); Garas & Vagg (2000[Garas, A. M. S. & Vagg, R. S. (2000). J. Heterocycl. Chem. 37, 151-158.]). For information on phenanthroline ligands as used in coordination chemistry, see: Sauvage (1990[Sauvage, J. P. (1990). Acc. Chem. Res. 23, 319-327.]). For the synthetic procedure, see: Schmittel & Ganz (1997[Schmittel, M. & Ganz, A. (1997). Chem. Commun. pp. 999-1000.]).

[Scheme 1]

Experimental

Crystal data

  • C21H18N2

  • Mr = 298.37

  • Monoclinic, P 21 /c

  • a = 14.5778 (19) Å

  • b = 8.9877 (11) Å

  • c = 13.5790 (11) Å

  • [beta] = 112.166 (4)°

  • V = 1647.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.35 × 0.23 × 0.19 mm
Data collection

  • Bruker SMART area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.976, Tmax = 0.987

  • 9474 measured reflections

  • 3511 independent reflections

  • 2150 reflections with I > 2[sigma](I)

  • Rint = 0.031
Refinement

  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.181

  • S = 1.06

  • 3511 reflections

  • 208 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. 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 for Windows (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2789 ).

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Garas, A. M. S. & Vagg, R. S. (2000). J. Heterocycl. Chem. 37, 151-158.  [CrossRef] [ChemPort]
Sauvage, J. P. (1990). Acc. Chem. Res. 23, 319-327.  [CrossRef] [ChemPort] [ISI]
Schmittel, M. & Ganz, A. (1997). Chem. Commun. pp. 999-1000.  [CrossRef]
Schmittel, M., Michel, C., Liu, S.-X., Schildbach, D. & Fenske, D. (2001). Eur. J. Inorg. Chem. pp. 1155-1166.  [CrossRef]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2009). E65, o932  [ doi:10.1107/S1600536809010800 ]

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