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Volume 69 
Part 7 
Page m424  
July 2013  

Received 18 June 2013
Accepted 20 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.036
wR = 0.096
Data-to-parameter ratio = 28.6
Details
Open access

Di-[mu]-bromido-bis[(diethyl ether-[kappa]O)(2,4,6-trimethylphenyl)magnesium]: the mesityl Grignard reagent

aInstitut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany
Correspondence e-mail: bolte@chemie.uni-frankfurt.de

The crystal structure of the title compound, [Mg2Br2(C9H11)2(C4H10O)2], features a centrosymmetric two-centre magnesium complex with half a molecule in the asymmetric unit. The Mg atom is in a considerably distorted Br2CO coordination. Bond lengths and angles are comparable with already published values. The crystal packing is stabilized by C-H...[pi] interactions linking the complexes into sheets parallel to (0-11).

Related literature

For literature on other Grignard reagents, see: Blasberg et al. (2012[Blasberg, F., Bolte, M., Wagner, M. & Lerner, H.-W. (2012). Organometallics, 31, 1001-1005.]); Bock et al. (1996[Bock, H., Ziemer, K. & Näther, C. (1996). J. Organomet. Chem. 511, 29-35.]); Cole et al. (2003[Cole, S. C., Coles, M. P. & Hitchcock, P. B. (2003). Dalton Trans. pp. 3663-3664.]); Ellison & Power (1996[Ellison, J. J. & Power, P. P. (1996). J. Organomet. Chem. 526, 263-267.]); Hübner et al. (2010[Hübner, A., Bernert, T., Sänger, I., Alig, E., Bolte, M., Fink, L., Wagner, M. & Lerner, H.-W. (2010). Dalton Trans. 39, 7528-7533.]); Hayashi et al. (2011[Hayashi, M., Bolte, M., Wagner, M. & Lerner, H.-W. (2011). Z. Anorg. Allg. Chem. 637, 646-649.]); Sakamoto et al. (2001[Sakamoto, S., Imamoto, T. & Yamaguchi, K. (2001). Org. Lett. 3, 1793-1795.]); Waggoner & Power (1992[Waggoner, K. M. & Power, P. P. (1992). Organometallics, 11, 3209-3214.]).

[Scheme 1]

Experimental

Crystal data
  • [Mg2Br2(C9H11)2(C4H10O)2]

  • Mr = 595.03

  • Triclinic, [P \overline 1]

  • a = 7.8516 (6) Å

  • b = 8.8285 (6) Å

  • c = 12.1356 (8) Å

  • [alpha] = 87.285 (6)°

  • [beta] = 82.516 (6)°

  • [gamma] = 65.396 (5)°

  • V = 758.30 (10) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 2.73 mm-1

  • T = 173 K

  • 0.23 × 0.19 × 0.13 mm

Data collection
  • Stoe IPDS II two-circle diffractometer

  • Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.572, Tmax = 0.718

  • 18010 measured reflections

  • 4227 independent reflections

  • 3839 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.096

  • S = 1.06

  • 4227 reflections

  • 148 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.70 e Å-3

  • [Delta][rho]min = -0.55 e Å-3

Table 1
Selected geometric parameters (Å, °)

Br1-Mg1 2.5503 (7)
Br1-Mg1i 2.5900 (7)
Mg1-O1 2.0243 (16)
Mg1-C11 2.123 (2)
O1-Mg1-C11 108.18 (7)
O1-Mg1-Br1 105.96 (5)
C11-Mg1-Br1 121.22 (6)
O1-Mg1-Br1i 100.23 (5)
C11-Mg1-Br1i 126.30 (6)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 phenyl ring.

D-H...A D-H H...A D-H...A
C3-H3B...Cg1ii 0.99 2.83 159
C18-H18B...Cg1iii 0.98 3.05 122
Symmetry codes: (ii) x-1, y, z; (iii) -x+2, -y, -z.

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2012[Sheldrick, G. M. (2012). SHELXL2012. University of Göttingen, Germany.]); molecular graphics: XP (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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: NG5334 ).


References

Blasberg, F., Bolte, M., Wagner, M. & Lerner, H.-W. (2012). Organometallics, 31, 1001-1005.  [CrossRef] [ChemPort]
Bock, H., Ziemer, K. & Näther, C. (1996). J. Organomet. Chem. 511, 29-35.  [CrossRef] [ChemPort]
Cole, S. C., Coles, M. P. & Hitchcock, P. B. (2003). Dalton Trans. pp. 3663-3664.  [CSD] [CrossRef]
Ellison, J. J. & Power, P. P. (1996). J. Organomet. Chem. 526, 263-267.  [CrossRef] [ChemPort]
Hayashi, M., Bolte, M., Wagner, M. & Lerner, H.-W. (2011). Z. Anorg. Allg. Chem. 637, 646-649.  [CSD] [CrossRef] [ChemPort]
Hübner, A., Bernert, T., Sänger, I., Alig, E., Bolte, M., Fink, L., Wagner, M. & Lerner, H.-W. (2010). Dalton Trans. 39, 7528-7533.  [PubMed]
Sakamoto, S., Imamoto, T. & Yamaguchi, K. (2001). Org. Lett. 3, 1793-1795.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2012). SHELXL2012. University of Göttingen, Germany.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.
Waggoner, K. M. & Power, P. P. (1992). Organometallics, 11, 3209-3214.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, m424  [ doi:10.1107/S1600536813017108 ]

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