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Volume 69 
Part 8 
Pages m441-m442  
August 2013  

Received 21 June 2013
Accepted 1 July 2013
Online 6 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.033
wR = 0.087
Data-to-parameter ratio = 16.1
Details
Open access

Trichlorido(1,3-dimethyl-2,3-dihydro-1H-imidazol-2-ylidene-[kappa]C2)aluminium(III)

aCollege of Chemistry, Leshan Normal University, Binhe Rd 778, Leshan 614000, Sichuan Province, People's Republic of China, and bZhengzhou Research Institute of Comprehensive Utilization of Mineral Resourses of CAGS, Longhai Rd 328, Zhengzhou 450006, Henan Province, People's Republic of China
Correspondence e-mail: maxborzov@mail.ru

The title compound, [Al(C5H8N2)Cl3], was prepared by a thermolytic decomposition under high-vacuum conditions and presents a formal adduct of an Arduengo carbene, 1,3-dimethyl-1H-imidazol-2-ylidene, and aluminium trichloride. The Al atom adopts a pseudo-tetrahedral CCl3 coordination environment. All N and C atoms, the Al atom, one of the Cl atoms, and all aromatic H atoms of the molecule lie on a mirror plane. As a result of the mirror symmetry of the molecule, the H atoms of all methyl groups are disordered between symmetry-equivalent positions.

Related literature

For related structurally characterized Arduengo carbene AlX3 (X = Cl, I) adducts, see: Stasch et al. (2004[Stasch, A., Singh, S., Roesky, H. W., Noltemeyer, M. & Schmidt, H.-G. (2004). Eur. J. Inorg. Chem. pp. 4052-4055.]); Ghadwal et al. (2009[Ghadwal, R. S., Roesky, H. W., Herbst-Irmer, R. & Jones, P. G. (2009). Z. Anorg. Allg. Chem. 635, 431-433.]); Bantu et al. (2009[Bantu, B., Pawar, G. M., Wurst, K., Decker, U., Schmidt, A. M. & Buschmeiser, M. R. (2009). Eur. J. Inorg. Chem. pp. 1970-1976.]). For thermolytic interconversion of sterically non-hindered 1,3-dialkyl-1H-imidazolium salts with BF4- and PF6- anions into Arduengo carbene adducts with BF3 and PF5, see: Tian et al. (2012[Tian, C., Nie, W., Borzov, M. V. & Su, P. (2012). Organometallics, 31, 1751-1760.]). For the crystal structure of the precursor employed in the synthesis of the title compound, see: Tian et al. (2013[Tian, C., Chen, Q., Hu, W., Nie, W. & Borzov, M. V. (2013). Private communication (CCDC 945892). CCDC, Cambridge, England.]). 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
  • [Al(C5H8N2)Cl3]

  • Mr = 229.46

  • Orthorhombic, P n m a

  • a = 8.9075 (7) Å

  • b = 7.3903 (6) Å

  • c = 15.3253 (12) Å

  • V = 1008.85 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.94 mm-1

  • T = 296 K

  • 0.40 × 0.38 × 0.20 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.706, Tmax = 0.835

  • 5094 measured reflections

  • 1062 independent reflections

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

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.087

  • S = 1.07

  • 1062 reflections

  • 66 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Selected bond lengths (Å)

Cl1-Al1 2.1193 (12)
Cl2-Al1 2.1290 (7)
Al1-C1 2.006 (3)
Al1-Cl2i 2.1291 (7)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z].

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


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2754 ).


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 thankful to Mr Pengfei Su (Xi'an Modern Chemistry Research Institute, East Zhangba Road 168, Xi'an 71065, Shaanxi Province, China) for his help in performing the X-ray experiment.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Bantu, B., Pawar, G. M., Wurst, K., Decker, U., Schmidt, A. M. & Buschmeiser, M. R. (2009). Eur. J. Inorg. Chem. pp. 1970-1976.  [Web of Science] [CSD] [CrossRef]
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
Ghadwal, R. S., Roesky, H. W., Herbst-Irmer, R. & Jones, P. G. (2009). Z. Anorg. Allg. Chem. 635, 431-433.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stasch, A., Singh, S., Roesky, H. W., Noltemeyer, M. & Schmidt, H.-G. (2004). Eur. J. Inorg. Chem. pp. 4052-4055.  [Web of Science] [CSD] [CrossRef]
Tian, C., Chen, Q., Hu, W., Nie, W. & Borzov, M. V. (2013). Private communication (CCDC 945892). CCDC, Cambridge, England.
Tian, C., Nie, W., Borzov, M. V. & Su, P. (2012). Organometallics, 31, 1751-1760.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, m441-m442   [ doi:10.1107/S1600536813018254 ]

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