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Volume 69 
Part 6 
Page o928  
June 2013  

Received 8 May 2013
Accepted 14 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.050
wR = 0.155
Data-to-parameter ratio = 14.9
Details
Open access

4-Diphenylphosphanyl-8-methyl-1,5-naphthyridine

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
Correspondence e-mail: zhuhjnjut@hotmail.com

In the title compound, C21H17N2P, the dihedral angles between the 1,5-naphthyridine ring system (r.m.s. deviation = 0.005 Å) and the phenyl rings are 89.18 (8) and 77.39 (8)°. The phenyl rings are almost perpendicular, making a dihedral angle of 88.12 (8)°. The only possible intermolecular interaction is a very weak aromatic [pi]-[pi] stacking interaction [centroid-centroid separation = 3.898 (2) Å].

Related literature

For further synthetic details and background to the role of the title compound as an intermediate in the synthesis of OLED materials, see: Chen et al. (2012[Chen, C., Wang, K., Jiang, P., Song, G. & Zhu, H. (2012). Inorg. Chem. Commun. 17, 116-119.]).

[Scheme 1]

Experimental

Crystal data
  • C21H17N2P

  • Mr = 328.34

  • Triclinic, [P \overline 1]

  • a = 7.2320 (14) Å

  • b = 7.4470 (15) Å

  • c = 16.780 (3) Å

  • [alpha] = 99.78 (3)°

  • [beta] = 93.35 (3)°

  • [gamma] = 98.58 (3)°

  • V = 877.4 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.16 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.954, Tmax = 0.984

  • 3500 measured reflections

  • 3224 independent reflections

  • 2285 reflections with I > 2[sigma](I)

  • Rint = 0.023

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.155

  • S = 1.00

  • 3224 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7082 ).


Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Chen, C., Wang, K., Jiang, P., Song, G. & Zhu, H. (2012). Inorg. Chem. Commun. 17, 116-119.  [ISI] [CSD] [CrossRef] [ChemPort]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o928  [ doi:10.1107/S1600536813013196 ]

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