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Volume 67 
Part 5 
Pages m549-m550  
May 2011  

Received 23 March 2011
Accepted 3 April 2011
Online 7 April 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.040
wR = 0.102
Data-to-parameter ratio = 15.8
Details
Open access

{2-[([eta]5-Cyclopentadienyl)diphenylmethyl]-1H-imidazolido-[kappa]N}bis(N,N-diethylamido)titanium(IV)

aKey Laboratory of Synthetic and Natural Chemistry of the Ministry of Education, College of Chemistry and Material Science, The North-West University of Xi'an, Taibai Bei Avenue 229, Xi'an 710069, Shaanxi Province, People's Republic of China
Correspondence e-mail: niewl126@126.com

The chemically achiral title molecule, [Ti(C4H10N)2(C21H16N2)], crystallizes in the chiral space group P21. All three N atoms coordinating to the TiIV atom adopt planar environments [sums of valence angles = 359.5 (6), 360.0 (7) and 360.0 (6)°], which is indicative of p[pi]-d[pi] donation from all of these N atoms to the metal and, thus, of the formal 18 e- nature of the complex. The overall coordination about the TiIV atom is distorted tetrahedral, assuming the cyclopentadienyl ring occupies one coordination site. The Ti-Nimidazole amide-type bond is longer by approximately 0.16 Å than the other two Ti-Namide bonds.

Related literature

For structural parameters of [eta]5-CpTi-tris(sec-amido)-type complexes, see: Rhodes et al. (2002[Rhodes, B., Chien, J. C. W., Wood, J. S., Chandrasekaran, A. & Rausch, M. D. (2002). Appl. Organomet. Chem. 16, 323-330.]); Li et al. (2003[Li, H., Li, L., Marks, T. J., Liable-Sands, L. & Rheingold, A. L. (2003). J. Am. Chem. Soc. 125, 10788-10789.]); Seo et al. (2001[Seo, W. S., Cho, Y. J., Yoon, S. C., Park, J. T. & Park, Y. (2001). J. Organomet. Chem. 640, 79-84.]); Kunz et al. (2001[Kunz, K., Erker, G., Doering, S., Froehlich, R. & Kehr, G. (2001). J. Am. Chem. Soc. 123, 6181-6182.], 2002[Kunz, K., Erker, G., Doering, S., Bredeau, S., Kehr, G. & Froehlich, R. (2002). Organometallics, 21, 1031-1041.]); Carpenetti et al. (1996[Carpenetti, D. W., Kloppenburg, L., Kupec, J. T. & Petersen, J. L. (1996). Organometallics, 15, 1572-1581.]); Bertolasi et al. (2007[Bertolasi, V., Boaretto, R., Chierotti, M. R., Gobetto, R. & Sostero, S. (2007). J. Chem. Soc. Dalton Trans. pp. 5179-5189.]); Wu et al. (2006[Wu, C. J., Lee, S. H., Yun, H. & Lee, B. Y. (2006). J. Organomet. Chem. 691, 5626-5634.]); Cano et al. (2005[Cano, J., Sudupe, M., Royo, P. & Mosquera, M. E. G. (2005). Organometallics, 24, 2424-2432.]); Martin et al. (1994[Martin, A., Mena, M., Yelamos, C., Serrano, R. & Raithby, P. R. (1994). J. Organomet. Chem. 467, 79-84.]). For two related TiIV complexes, see: Wang et al. (2009[Wang, X., Nie, W., Ge, F. & Borzov, M. V. (2009). Acta Cryst. C65, m255-m259.]). For the structural parameters of 1H-imidazol(in)-2-yl side-chain functionalized cyclopentadienes and their Li, Ti, and Zr complexes, see: Krut'ko et al. (2006[Krut'ko, D. P., Borzov, M. V., Liao, L., Nie, W., Churakov, A. V., Howard, J. A. K. & Lemenovskii, D. A. (2006). Russ. Chem. Bull. 55, 1574-1580.]); Nie et al. (2008[Nie, W., Liao, L., Xu, W., Borzov, M. V., Krut'ko, D. P., Churakov, A. V., Howard, J. A. K. & Lemenovskii, D. A. (2008). J. Organomet. Chem. 693, 2355-2368.]); Sun et al. (2009[Sun, G., Tian, C., Nie, W. & Borzov, M. V. (2009). Acta Cryst. E65, m478.], 2010[Sun, Q., Nie, W. & Borzov, M. V. (2010). Acta Cryst. E66, o285-o286.]); Ge et al. (2010[Ge, F., Nie, W., Borzov, M. V. & Churakov, A. V. (2010). Acta Cryst. E66, m546-m547.]). For synthetic details, see: Curtis & Brown (1980[Curtis, N. J. & Brown, R. S. (1980). J. Org. Chem. 45, 4038-4040.]); Bürger & Dämmen (1974[Bürger, H. & Dämmen, U. (1974). Z. Anorg. Allg. Chem. 407, 201-210.]); Bradley & Thomas (1960[Bradley, D. C. & Thomas, I. M. (1960). J. Chem. Soc. pp. 3857-3861.]); Chajara & Ottosson (2004[Chajara, K. & Ottosson, H. (2004). Tetrahedron Lett. 45, 6741-6744.]); Armarego & Perrin (1997[Armarego, W. L. F. & Perrin, D. D. (1997). Purification of Laboratory Chemicals, 4th ed. Oxford: Pergamon.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • [Ti(C4H10N)2(C21H16N2)]

  • Mr = 488.52

  • Monoclinic, P 21

  • a = 8.6495 (6) Å

  • b = 17.9486 (12) Å

  • c = 9.1130 (6) Å

  • [beta] = 110.603 (1)°

  • V = 1324.27 (15) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 296 K

  • 0.35 × 0.23 × 0.08 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.888, Tmax = 0.973

  • 7145 measured reflections

  • 4906 independent reflections

  • 4031 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.102

  • S = 0.99

  • 4906 reflections

  • 311 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2209 Friedel pairs

  • Flack parameter: 0.02 (3)

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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: 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2469 ).


Acknowledgements

Financial support from the National Natural Science Foundation of China (project Nos. 20702041 and 21072157) and the Shaanxi Province Administration of Foreign Experts Bureau Foundation (grant No. 20106100079) is gratefully acknowledged. The authors are grateful to Mr Wang Minchang and Mr Su Pengfei (Xi'an Modern Chemistry Research Institute) for their help in carrying out the NMR spectroscopy and X-ray diffraction experiments.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Armarego, W. L. F. & Perrin, D. D. (1997). Purification of Laboratory Chemicals, 4th ed. Oxford: Pergamon.
Bertolasi, V., Boaretto, R., Chierotti, M. R., Gobetto, R. & Sostero, S. (2007). J. Chem. Soc. Dalton Trans. pp. 5179-5189.
Bradley, D. C. & Thomas, I. M. (1960). J. Chem. Soc. pp. 3857-3861.  [CrossRef]
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bürger, H. & Dämmen, U. (1974). Z. Anorg. Allg. Chem. 407, 201-210.
Cano, J., Sudupe, M., Royo, P. & Mosquera, M. E. G. (2005). Organometallics, 24, 2424-2432.  [CSD] [CrossRef] [ChemPort]
Carpenetti, D. W., Kloppenburg, L., Kupec, J. T. & Petersen, J. L. (1996). Organometallics, 15, 1572-1581.  [CrossRef] [ChemPort]
Chajara, K. & Ottosson, H. (2004). Tetrahedron Lett. 45, 6741-6744.  [ChemPort]
Curtis, N. J. & Brown, R. S. (1980). J. Org. Chem. 45, 4038-4040.  [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Ge, F., Nie, W., Borzov, M. V. & Churakov, A. V. (2010). Acta Cryst. E66, m546-m547.  [CrossRef] [details]
Krut'ko, D. P., Borzov, M. V., Liao, L., Nie, W., Churakov, A. V., Howard, J. A. K. & Lemenovskii, D. A. (2006). Russ. Chem. Bull. 55, 1574-1580.  [ChemPort]
Kunz, K., Erker, G., Doering, S., Bredeau, S., Kehr, G. & Froehlich, R. (2002). Organometallics, 21, 1031-1041.  [CSD] [CrossRef] [ChemPort]
Kunz, K., Erker, G., Doering, S., Froehlich, R. & Kehr, G. (2001). J. Am. Chem. Soc. 123, 6181-6182.  [ISI] [CrossRef] [PubMed] [ChemPort]
Li, H., Li, L., Marks, T. J., Liable-Sands, L. & Rheingold, A. L. (2003). J. Am. Chem. Soc. 125, 10788-10789.  [ISI] [CrossRef] [PubMed] [ChemPort]
Martin, A., Mena, M., Yelamos, C., Serrano, R. & Raithby, P. R. (1994). J. Organomet. Chem. 467, 79-84.  [CrossRef] [ChemPort]
Nie, W., Liao, L., Xu, W., Borzov, M. V., Krut'ko, D. P., Churakov, A. V., Howard, J. A. K. & Lemenovskii, D. A. (2008). J. Organomet. Chem. 693, 2355-2368.  [CrossRef] [ChemPort]
Rhodes, B., Chien, J. C. W., Wood, J. S., Chandrasekaran, A. & Rausch, M. D. (2002). Appl. Organomet. Chem. 16, 323-330.  [ISI] [CSD] [CrossRef] [ChemPort]
Seo, W. S., Cho, Y. J., Yoon, S. C., Park, J. T. & Park, Y. (2001). J. Organomet. Chem. 640, 79-84.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sun, Q., Nie, W. & Borzov, M. V. (2010). Acta Cryst. E66, o285-o286.  [CrossRef] [details]
Sun, G., Tian, C., Nie, W. & Borzov, M. V. (2009). Acta Cryst. E65, m478.  [CSD] [CrossRef] [details]
Wang, X., Nie, W., Ge, F. & Borzov, M. V. (2009). Acta Cryst. C65, m255-m259.  [CSD] [CrossRef] [details]
Wu, C. J., Lee, S. H., Yun, H. & Lee, B. Y. (2006). J. Organomet. Chem. 691, 5626-5634.  [ChemPort]


Acta Cryst (2011). E67, m549-m550   [ doi:10.1107/S1600536811012396 ]

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