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Volume 69 
Part 5 
Page o679  
May 2013  

Received 6 March 2013
Accepted 27 March 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.030
wR = 0.070
Data-to-parameter ratio = 23.1
Details
Open access

1,3,5-Tris(bromomethyl)-2,4,6-trimethoxybenzene

aInstitut für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
Correspondence e-mail: monika.mazik@chemie.tu-freiberg.de

There are three independent molecules in the asymmetric unit of the title compound, C12H15Br3O3, two of which have approximate trigonal symmetry, the third being conformationally different as it adopts near mirror symmetry. The crystal structure features C-H...Br interactions, a weak C-H...O hydrogen bond, [pi]-[pi] interactions [minimum ring centroid separation = 3.4927 (18) Å] and a short Br...Br contact [3.5894 (5) Å], resulting in a three-dimensional supramolecular network.

Related literature

For the synthesis and sample applications of the title compound, see: Li et al. (2005[Li, H., Homan, E. A., Lampkins, A. J., Ghiviriga, I. & Castellano, R. K. (2005). Org. Lett. 7, 443-446.]); Kim et al. (2005[Kim, J., Kim, Y., Park, N., Hahn, J. H. & Ahn, K. H. (2005). J. Org. Chem. 70, 7087-7092.]); Holec et al. (2011[Holec, J., Rybácek, J., Budesínsky, M., Pospísil, L. & Holý, P. (2011). Monatsh. Chem. 142, 821-826.]); Simaan et al. (2003[Simaan, S., Siegel, J. S. & Biali, S. (2003). J. Org. Chem. 68, 3699-3701.]); Whiting & Hof (2012[Whiting, A. L. & Hof, F. (2012). Org. Biomol. Chem. 10, 6885-6892.]). For hydrogen bonds, see: Desiraju (2002[Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565-573.]); Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]). For halogen bonding, see: Awwadi et al. (2006[Awwadi, F. F., Willett, R. D., Peterson, K. A. & Twamley, B. (2006). Chem. Eur. J. 12, 8952-8960.]); Metrangolo & Resnati (2008[Metrangolo, P. & Resnati, G. (2008). Halogen Bonding: Fundamentals and Applications. pp. 181-191. Berlin: Springer.]).

[Scheme 1]

Experimental

Crystal data
  • C12H15Br3O3

  • Mr = 446.94

  • Triclinic, [P \overline 1]

  • a = 9.7508 (5) Å

  • b = 15.0974 (7) Å

  • c = 16.5500 (7) Å

  • [alpha] = 114.433 (2)°

  • [beta] = 92.903 (2)°

  • [gamma] = 97.510 (2)°

  • V = 2184.29 (18) Å3

  • Z = 6

  • Mo K[alpha] radiation

  • [mu] = 8.31 mm-1

  • T = 100 K

  • 0.55 × 0.44 × 0.27 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.092, Tmax = 0.213

  • 44729 measured reflections

  • 11474 independent reflections

  • 9330 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.070

  • S = 1.02

  • 11474 reflections

  • 496 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.17 e Å-3

  • [Delta][rho]min = -1.10 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8A-H8A1...Br1A 0.98 2.91 3.787 (3) 150
C8-H8A...Br1 0.98 2.84 3.702 (3) 148
C8-H8C...Br2 0.98 2.86 3.670 (3) 140
C7B-H7B2...Br3Bi 0.99 2.92 3.665 (3) 133
C10-H10A...Br2 0.98 2.85 3.717 (3) 149
C10-H10C...Br3 0.98 2.89 3.673 (3) 138
C10A-H10D...Br3A 0.98 2.78 3.659 (4) 149
C10B-H10G...Br2B 0.98 2.72 3.606 (3) 151
C10B-H10I...Br3B 0.98 2.86 3.663 (3) 140
C11-H11B...O1Aii 0.99 2.55 3.429 (4) 148
C8B-H8B3...Br2B 0.98 2.85 3.697 (4) 146
C12B-H12G...Br3B 0.98 2.83 3.702 (3) 149
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2251 ).


Acknowledgements

This work was supported by the Deutsche Forschungsgemeinschaft.

References

Awwadi, F. F., Willett, R. D., Peterson, K. A. & Twamley, B. (2006). Chem. Eur. J. 12, 8952-8960.  [CrossRef] [PubMed] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565-573.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Holec, J., Rybácek, J., Budesínsky, M., Pospísil, L. & Holý, P. (2011). Monatsh. Chem. 142, 821-826.  [CrossRef] [ChemPort]
Kim, J., Kim, Y., Park, N., Hahn, J. H. & Ahn, K. H. (2005). J. Org. Chem. 70, 7087-7092.  [CrossRef] [PubMed] [ChemPort]
Li, H., Homan, E. A., Lampkins, A. J., Ghiviriga, I. & Castellano, R. K. (2005). Org. Lett. 7, 443-446.  [ISI] [CrossRef] [PubMed] [ChemPort]
Metrangolo, P. & Resnati, G. (2008). Halogen Bonding: Fundamentals and Applications. pp. 181-191. Berlin: Springer.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Simaan, S., Siegel, J. S. & Biali, S. (2003). J. Org. Chem. 68, 3699-3701.  [CSD] [CrossRef] [PubMed] [ChemPort]
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.  [ISI] [CrossRef] [ChemPort]
Whiting, A. L. & Hof, F. (2012). Org. Biomol. Chem. 10, 6885-6892.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o679  [ doi:10.1107/S1600536813008441 ]

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