[Journal logo]

Volume 69 
Part 11 
Page m590  
November 2013  

Received 4 August 2013
Accepted 22 September 2013
Online 9 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.008 Å
R = 0.032
wR = 0.066
Data-to-parameter ratio = 14.2
Details
Open access

[2,6-Di­fluoro-3-(pyridin-2-yl-[kappa]N)pyridin-4-yl-[kappa]C4](penta­ne-2,4-dionato-[kappa]2O,O')iridium(III)

aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu, Sichuan 610068, People's Republic of China, and bAnalytical and Testing Center, Sichuan University, Chengdu, Sichuan 610065, People's Republic of China
Correspondence e-mail: luodaibing690312@163.com

The title compound, [Ir(C10H5F2N2)2(C5H7O2)], has a distorted octa­hedral coordination geometry around the IrIII atom, retaining the cis-C,C/trans-N,N chelate disposition in two 2,6-di­fluoro-3-(pyridin-2-yl-[kappa]N)pyridin-4-yl ligands which are nearly mutually perpendicular [dihedral angle = 82.75 (15)°]. The mol­ecular structure is stabilized by weak C-H...O and C-H...F hydrogen-bond inter­actions. The crystal structure is stabilized by [pi]-[pi] stacking inter­actions (centroid-centroid distance = 3.951 Å).

Related literature

For general background and related structures, see: Xiao et al. (2011[Xiao, L. X., Chen, Z. J., Qu, B., Luo, J. X., Kong, S. & Gong, Q. H. (2011). Adv. Mater. 23, 926-952.]); Lamansky et al. (2001a[Lamansky, S., Djurovich, P., Murphy, D., Abdel-Razzaq, F., Kwong, R., Tsyba, I., Bortz, M., Mui, B., Bau, R. & Thompson, M. E. (2001a). Inorg. Chem. 40, 1704-1711.]); Lee et al. (2009[Lee, S. J., Park, K. M., Yang, K. & Kang, Y. G. (2009). Inorg. Chem. 48, 1030-1037.]); Jung et al. (2012[Jung, N., Lee, E. J., Kim, J., Park, H. G., Park, K. M. & Kang, Y. G. (2012). Bull. Korean Chem. Soc. 33, 183-188.]). For the synthesis of the title complex, see: Lamansky et al. (2001b[Lamansky, S., Djurovich, P., Murphy, D., Abdel-Razzaq, F., Lee, H. E., Adachi, C., Burrows, P. E., Forrest, S. R. & Thompson, M. E. (2001b). J. Am. Chem. Soc. 123, 4304-4312.]); Luo et al. (2011[Luo, K. J., Jiang, S. P., Wang, X., Deng, X. P., Zhu, W. G., Zhao, K. Q. & Xie, Y. (2011). Chin. J. Lumin., 32, 369-373.]).

[Scheme 1]

Experimental

Crystal data
  • [Ir(C10H5F2N2)2(C5H7O2)]

  • Mr = 673.63

  • Monoclinic, P 21 /n

  • a = 7.7126 (2) Å

  • b = 18.2039 (5) Å

  • c = 16.3534 (4) Å

  • [beta] = 99.371 (3)°

  • V = 2265.38 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 5.96 mm-1

  • T = 293 K

  • 0.40 × 0.35 × 0.35 mm

Data collection
  • Agilent Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.400, Tmax = 1.000

  • 9371 measured reflections

  • 4628 independent reflections

  • 3736 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.066

  • S = 1.03

  • 4628 reflections

  • 327 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.17 e Å-3

  • [Delta][rho]min = -0.97 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1...O2 0.93 2.56 3.146 (6) 121
C4-H4...F2 0.93 2.36 2.894 (7) 121
C11-H11...O1 0.93 2.59 3.175 (7) 121
C14-H14...F4 0.93 2.33 2.915 (7) 121

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2449 ).


Acknowledgements

Support from the National Natural Science Foundation of China (grant Nos. 21072141 and 21172161) is gratefully acknowledged.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Jung, N., Lee, E. J., Kim, J., Park, H. G., Park, K. M. & Kang, Y. G. (2012). Bull. Korean Chem. Soc. 33, 183-188.  [ChemPort]
Lamansky, S., Djurovich, P., Murphy, D., Abdel-Razzaq, F., Kwong, R., Tsyba, I., Bortz, M., Mui, B., Bau, R. & Thompson, M. E. (2001a). Inorg. Chem. 40, 1704-1711.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Lamansky, S., Djurovich, P., Murphy, D., Abdel-Razzaq, F., Lee, H. E., Adachi, C., Burrows, P. E., Forrest, S. R. & Thompson, M. E. (2001b). J. Am. Chem. Soc. 123, 4304-4312.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Lee, S. J., Park, K. M., Yang, K. & Kang, Y. G. (2009). Inorg. Chem. 48, 1030-1037.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Luo, K. J., Jiang, S. P., Wang, X., Deng, X. P., Zhu, W. G., Zhao, K. Q. & Xie, Y. (2011). Chin. J. Lumin., 32, 369-373.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Xiao, L. X., Chen, Z. J., Qu, B., Luo, J. X., Kong, S. & Gong, Q. H. (2011). Adv. Mater. 23, 926-952.  [Web of Science] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, m590  [ doi:10.1107/S1600536813026160 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.