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Volume 69 
Part 2 
Page m98  
February 2013  

Received 14 December 2012
Accepted 5 January 2013
Online 12 January 2013

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.015 Å
R = 0.058
wR = 0.099
Data-to-parameter ratio = 14.3
Details
Open access

(4-Chloroacetanilido-[kappa]2N,O)bis[2-(pyridin-2-yl)phenyl-[kappa]2C1,N]iridium(III)

Lijun Sun,a Songlin Zhanga* and Qijun Songa

aSchool of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, People's Republic of China
Correspondence e-mail: slzhang@jiangnan.edu.cn

In the neutral mononuclear iridium(III) title compound, [Ir(C8H7ClNO)(C11H8N)2], the IrIII atom adopts an octahedral geometry, and is coordinated by two 2-phenylpyridyl ligands and one anionic 4-chloroacetanilide ligand. The 2-phenylpyridyl ligands are arranged in a cis-C,C' and cis-N,N' fashion. Each 2-phenylpyridyl ligand forms a five-membered ring with the IrIII atom. The 2-phenylpyridyl planes are perpendicular to each other [dihedral angle = 89.9 (1)°]. The Ir-C and Ir-N bond lengths are comparable to those reported for related iridium(III) 2-phenylpyridyl complexes. The remaining two coordination sites are occupied by the amidate N and O atoms, which form a four-membered ring with the iridium atom (Ir-N-C-O). The amidate plane is nearly perpendicular to both 2-phenylpyridyl ligands [dihedral angles = 87.8 (2) and 88.3 (2)°].

Related literature

For related iridium(III) complexes containing 2-phenylpyridyl derivatives as cyclometalating ligands, see: Lamansky et al. (2001[Lamansky, S., Djurovich, P., Murphy, D., Abdel-Razzaq, F., Kwong, R., Tsyba, I., Bortz, M., Mui, B., Bau, R. & Thompson, M. E. (2001). Inorg. Chem. 40, 1704-1711.]); Tamayo et al. (2003[Tamayo, A. B., Alleyne, B. D., Djurovich, P. I., Lamansky, S. L., Tsyba, I., Ho, N. N., Bau, R. & Thompson, M. E. (2003). J. Am. Chem. Soc. 125, 7377-7387.]); Yang et al. (2011[Yang, W., Fu, H., Song, Q., Zhang, M. & Ding, Y. (2011). Organometallics, 30, 77-83.]); You & Park (2005[You, Y. & Park, S. Y. (2005). J. Am. Chem. Soc. 127, 12438-12439.]); Zhang et al. (2011[Zhang, S., Wu, F., Yang, W. & Ding, Y. (2011). Inorg. Chem. Commun. 14, 1414-1417.]). For the coordination geometry of some heteroleptic iridium(III) complexes containing amidate ancillary ligands, see: Yang et al. (2011[Yang, W., Fu, H., Song, Q., Zhang, M. & Ding, Y. (2011). Organometallics, 30, 77-83.]); Zhang et al. (2011[Zhang, S., Wu, F., Yang, W. & Ding, Y. (2011). Inorg. Chem. Commun. 14, 1414-1417.]). For a general procedure for the preparation of a chloride-bridged iridium(III) dimer, see: Nonoyama (1974[Nonoyama, M. (1974). Bull. Chem. Soc. Jpn, 47, 767-768.]).

[Scheme 1]

Experimental

Crystal data

  • [Ir(C8H7ClNO)(C11H8N)2]

  • Mr = 669.16

  • Orthorhombic, P b c a

  • a = 12.8391 (15) Å

  • b = 11.0697 (13) Å

  • c = 35.897 (4) Å

  • V = 5101.8 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 5.37 mm-1

  • T = 293 K

  • 0.58 × 0.20 × 0.20 mm
Data collection

  • Rigaku Mercury diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998[Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.073, Tmax = 0.584

  • 41875 measured reflections

  • 4668 independent reflections

  • 4140 reflections with I > 2[sigma](I)

  • Rint = 0.064
Refinement

  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.099

  • S = 1.11

  • 4668 reflections

  • 326 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.56 e Å-3

  • [Delta][rho]min = -0.76 e Å-3

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: PK2461 ).

Acknowledgements

This study was supported by the National Natural Science Foundation of China (grant No. 21202062), the Natural Science Foundation of Jiangsu Province, China (grant No. BK2012108) and the Fundamental Research Funds for Central Universities (grant No. JUSRP 11105).

References

Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.
Lamansky, S., Djurovich, P., Murphy, D., Abdel-Razzaq, F., Kwong, R., Tsyba, I., Bortz, M., Mui, B., Bau, R. & Thompson, M. E. (2001). Inorg. Chem. 40, 1704-1711.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Nonoyama, M. (1974). Bull. Chem. Soc. Jpn, 47, 767-768.  [CrossRef] [ChemPort] [ISI]
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tamayo, A. B., Alleyne, B. D., Djurovich, P. I., Lamansky, S. L., Tsyba, I., Ho, N. N., Bau, R. & Thompson, M. E. (2003). J. Am. Chem. Soc. 125, 7377-7387.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Yang, W., Fu, H., Song, Q., Zhang, M. & Ding, Y. (2011). Organometallics, 30, 77-83.  [CSD] [CrossRef] [ChemPort]
You, Y. & Park, S. Y. (2005). J. Am. Chem. Soc. 127, 12438-12439.  [ISI] [CrossRef] [PubMed] [ChemPort]
Zhang, S., Wu, F., Yang, W. & Ding, Y. (2011). Inorg. Chem. Commun. 14, 1414-1417.  [ISI] [CSD] [CrossRef] [ChemPort]

Acta Cryst (2013). E69, m98  [ doi:10.1107/S1600536813000433 ]

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