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Volume 69 
Part 4 
Pages m224-m225  
April 2013  

Received 6 March 2013
Accepted 18 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
R = 0.028
wR = 0.071
Data-to-parameter ratio = 23.6
Details
Open access

Chlorido[1-(2-oxidophenyl)ethylidene][tris(3,5-dimethylpyrazol-1-yl)hydroborato]iridium(III) chloroform monosolvate

aInstituto de Investigaciones Químicas (IIQ) and Departamento de Química Inorgánica, Consejo Superior de Investigaciones Cientificas (CSIC) and Universidad de Sevilla, Avenida Américo Vespucio 49, 41092 Sevilla, Spain, and bInstitute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna, Austria
Correspondence e-mail: kurt.mereiter@tuwien.ac.at

In the title compound, [Ir(C15H22BN6)(C8H7O)Cl]·CHCl3, the Ir atom is formally trivalent and is coordinated in a slightly distorted octahedral geometry by three facial N atoms, one C atom, one O atom and one Cl atom. The Ir=Ccarbene bond is strong and short and exerts a notable effect on the trans-Ir-N bond, which is about 0.10 Å longer than the two other Ir-N bonds. The chloroform solvent molecule is anchored via a weak C-H...Cl hydrogen bond to the Cl atom of the Ir complex molecule. In the crystal, the constituents adopt a layer-like arrangement parallel to (010) and are held together by weak intermolecular C-H...Cl hydrogen bonds, as well as weak Cl...Cl [3.498 (2) Å] and Cl...[pi] [3.360 (4) Å] interactions. A weak intramolecular C-H...O hydrogen bond is also observed.

Related literature

The title compound represents a well crystallizing air-stable chloroform solvate of a mononuclear iridium complex based on the (hydrogen tris(3,5-dimethylpyrazolyl)borate-N,N',N'')-iridium moiety Ir[TpMe2]. Its formation from [(TpMe2)Ir(C6H5)2(k1-N2)] (C6H5 = phenyl, N2 = dinitrogen) and ethoxybenzene involved multiple C-C,H,O,Cl bond transformations by the outstanding activity of the Ir[TpMe2] moiety. For general information on C-H and C-C activation, see: Lin & Yamamoto (1999[Lin, Y.-S. & Yamamoto, A. (1999). In Activation of Unreactive Bonds and Organic Synthesis, edited by S. Murai. Berlin: Springer.]); Dyker (1999[Dyker, G. (1999). Angew. Chem. Int. Ed. 38, 1698-1712.]); Labinger & Bercaw (2002[Labinger, J. A. & Bercaw, J. E. (2002). Nature, 417, 507-514.]). For C-H bond activation reactions of ethers by Ir[TpMe2] complexes, see: Lara et al. (2009[Lara, P., Paneque, M., Poveda, M. L., Santos, L. L., Valpuesta, J. E. V., Carmona, E., Moncho, S., Ujaque, G., Lledós, A., Álvarez, E. & Mereiter, K. (2009). Chem. Eur. J. 15, 9034-9045.]); Conejero et al. (2010[Conejero, S., Paneque, M., Poveda, M. L., Santos, L. L. & Carmona, E. (2010). Acc. Chem. Res. 43, 572-580.]); Santos et al. (2013[Santos, L. L., Mereiter, K. & Paneque, M. (2013). Organometallics, 32, 565-569.]). For the synthesis of the complex and related crystal structures, see: Gutiérrez-Puebla et al. (1998[Gutiérrez-Puebla, E., Monge, A., Nicasio, M. C., Pérez, P. J., Poveda, M. L. & Carmona, E. (1998). Chem. Eur. J. 4, 2225-2236.]); Lara et al. (2009[Lara, P., Paneque, M., Poveda, M. L., Santos, L. L., Valpuesta, J. E. V., Carmona, E., Moncho, S., Ujaque, G., Lledós, A., Álvarez, E. & Mereiter, K. (2009). Chem. Eur. J. 15, 9034-9045.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For bond-length data, 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. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • [Ir(C15H22BN6)(C8H7O)Cl]·CHCl3

  • Mr = 763.35

  • Monoclinic, P 21 /c

  • a = 10.1271 (4) Å

  • b = 19.1711 (8) Å

  • c = 14.3154 (6) Å

  • [beta] = 91.956 (2)°

  • V = 2777.7 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 5.22 mm-1

  • T = 173 K

  • 0.32 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.343, Tmax = 0.593

  • 52411 measured reflections

  • 8053 independent reflections

  • 6999 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.028

  • wR(F2) = 0.071

  • S = 1.02

  • 8053 reflections

  • 341 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.29 e Å-3

  • [Delta][rho]min = -1.43 e Å-3

Table 1
Selected bond lengths (Å)

Ir1-C22 1.937 (3)
Ir1-N3 2.056 (3)
Ir1-N1 2.059 (3)
Ir1-O1 2.063 (2)
Ir1-N5 2.155 (3)
Ir1-Cl1 2.3500 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C24-H24...Cl1 1.00 2.55 3.488 (5) 156
C11-H11A...O1 0.98 2.37 3.230 (4) 146
C11-H11C...Cl3i 0.98 2.65 3.609 (4) 166
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5594 ).


Acknowledgements

Financial support (FEDER) from the Spanish Ministry of Science (projects CTQ2010-17476 and Consolider-Ingenio 2010 CSD2007-00006) and the Junta de Andalucía (grant FQM-119 and project P09-FQM-4832) is acknowedged.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Conejero, S., Paneque, M., Poveda, M. L., Santos, L. L. & Carmona, E. (2010). Acc. Chem. Res. 43, 572-580.  [ISI] [CrossRef] [ChemPort] [PubMed]
Dyker, G. (1999). Angew. Chem. Int. Ed. 38, 1698-1712.  [CrossRef]
Gutiérrez-Puebla, E., Monge, A., Nicasio, M. C., Pérez, P. J., Poveda, M. L. & Carmona, E. (1998). Chem. Eur. J. 4, 2225-2236.
Labinger, J. A. & Bercaw, J. E. (2002). Nature, 417, 507-514.  [ISI] [CrossRef] [PubMed] [ChemPort]
Lara, P., Paneque, M., Poveda, M. L., Santos, L. L., Valpuesta, J. E. V., Carmona, E., Moncho, S., Ujaque, G., Lledós, A., Álvarez, E. & Mereiter, K. (2009). Chem. Eur. J. 15, 9034-9045.  [CSD] [CrossRef] [PubMed] [ChemPort]
Lin, Y.-S. & Yamamoto, A. (1999). In Activation of Unreactive Bonds and Organic Synthesis, edited by S. Murai. Berlin: Springer.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Santos, L. L., Mereiter, K. & Paneque, M. (2013). Organometallics, 32, 565-569.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m224-m225   [ doi:10.1107/S1600536813007344 ]

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