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Volume 69 
Part 3 
Page m159  
March 2013  

Received 29 January 2013
Accepted 13 February 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.010 Å
R = 0.037
wR = 0.063
Data-to-parameter ratio = 22.1
Details
Open access

(Pyridine-2-aldoximato-[kappa]2N,N')bis[2-(pyridin-2-yl)phenyl-[kappa]2C1,N]iridium(III)

aDepartment of Chemistry, International Institute of Information Technology, Bhubaneswar, Odisha 751 003, India
Correspondence e-mail: snpal75@gmail.com

In the title complex, [Ir(C11H8N)2(C6H5N2O)], the octahedrally coordinated IrIII atom is bonded to two 2-(pyridin-2-yl)phenyl ligands, through two phenyl C and two pydidine N atoms, and to one pyridine-2-aldoxime ligand through a pyridine N and an oxime N atom. The oxime O atom of the aldoxime unit forms intermolecular C-H...O hydrogen bonds, which result in a two-dimensional hydrogen-bonded polymeric network parallel to (100). C-H...[pi] interactions are also observed.

Related literature

For the synthesis of the iridium phenylpyridine starting material, see: Nonoyama (1974[Nonoyama, M. (1974). Bull. Chem. Soc. Jpn, 47, 767-768.]). For preparation of phenyl pyridine-based Ir(III) complexes, 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.]). For similar types of complexes, see: Neve et al. (1999[Neve, F., Crispini, A., Campagna, S. & Serroni, S. (1999). Inorg. Chem. 38, 2250-2258.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.]). For hydrogen bonding, see: Desiraju (1991[Desiraju, G. R. (1991). Acc. Chem. Res. 24, 290-296.]) and for C-H...[pi] interactions, see: Ma & Dougherty (1997[Ma, J. C. & Dougherty, D. A. (1997). Chem. Rev. 97, 1303-1324.]). For oxime ligands, see: Godycki & Rundle (1953[Godycki, L. E. & Rundle, R. E. (1953). Acta Cryst. 6, 487-495.]).

[Scheme 1]

Experimental

Crystal data
  • [Ir(C11H8N)2(C6H5N2O)]

  • Mr = 621.71

  • Monoclinic, P 21

  • a = 9.414 (1) Å

  • b = 14.226 (2) Å

  • c = 9.551 (1) Å

  • [beta] = 117.260 (7)°

  • V = 1137.0 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 5.90 mm-1

  • T = 293 K

  • 0.40 × 0.32 × 0.24 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS inc., Madison, Wisconsin, USA.]) Tmin = 0.201, Tmax = 0.332

  • 25091 measured reflections

  • 6898 independent reflections

  • 5718 reflections with I > 2[sigma](I)

  • Rint = 0.065

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.063

  • S = 0.96

  • 6898 reflections

  • 308 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 1.34 e Å-3

  • [Delta][rho]min = -0.83 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3193 Friedel pairs

  • Flack parameter: 0.007 (10)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C17-C22, N2/C12-C16 and N1/C1-C5 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C7-H7...O1i 0.93 2.35 3.235 (10) 159
C15-H15...O1ii 0.93 2.37 3.239 (9) 155
C3-H3...Cg1iii 0.93 2.74 3.604 (7) 155
C8-H8...Cg2i 0.93 2.69 3.606 (7) 170
C13-H13...Cg3iv 0.93 2.71 3.538 (9) 148
Symmetry codes: (i) x, y, z+1; (ii) [-x+1, y-{\script{1\over 2}}, -z]; (iii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iv) [-x, y-{\script{1\over 2}}, -z].

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS inc., Madison, Wisconsin, USA.]); cell refinement: SMART (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS inc., Madison, Wisconsin, USA.]); 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2497 ).


Acknowledgements

The authors would like to thank the Department of Science and Technology, Government of India (Fast-Track project, Grant No. SR/FT/CS-050/2009) for research funding. We also gratefully acknowlege the University of Hyderabad (India) single-crystal X-ray facility for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
Bruker (2003). SMART, SAINT and SADABS. Bruker AXS inc., Madison, Wisconsin, USA.
Desiraju, G. R. (1991). Acc. Chem. Res. 24, 290-296.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Godycki, L. E. & Rundle, R. E. (1953). Acta Cryst. 6, 487-495.  [CrossRef] [ChemPort] [details]
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]
Ma, J. C. & Dougherty, D. A. (1997). Chem. Rev. 97, 1303-1324.  [CrossRef] [PubMed] [ChemPort] [ISI]
Neve, F., Crispini, A., Campagna, S. & Serroni, S. (1999). Inorg. Chem. 38, 2250-2258.  [ISI] [CrossRef] [ChemPort]
Nonoyama, M. (1974). Bull. Chem. Soc. Jpn, 47, 767-768.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, m159  [ doi:10.1107/S1600536813004297 ]

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