[Journal logo]

Volume 68 
Part 1 
Page o109  
January 2012  

Received 3 October 2011
Accepted 8 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](C-C) = 0.014 Å
R = 0.091
wR = 0.227
Data-to-parameter ratio = 20.3
Details
Open access

2-(Dibromomethyl)benzoic acid

aDepartment of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan
Correspondence e-mail: kyuchen@fcu.edu.tw

In the crystal structure of the title compound, C8H6Br2O2, the carboxyl groups are involved in pairs of O-H...O hydrogen bonds, which link the molecules into inversion dimers.

Related literature

For the preparation of the title compound, see: Eliel & Rivard (1952[Eliel, E. L. & Rivard, D. E. (1952). J. Org. Chem. 17, 1252-1256.]). For its applications, see: Dey & Mal (2005[Dey, S. & Mal, D. (2005). Tetrahedron Lett. 46, 5483-5486.]). For graph-set theory, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C8H6Br2O2

  • Mr = 293.95

  • Monoclinic, P 21 /n

  • a = 4.9988 (6) Å

  • b = 25.617 (3) Å

  • c = 7.1844 (8) Å

  • [beta] = 97.709 (10)°

  • V = 911.68 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 8.85 mm-1

  • T = 297 K

  • 0.74 × 0.36 × 0.25 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.251, Tmax = 1.000

  • 7515 measured reflections

  • 2210 independent reflections

  • 1221 reflections with I > 2[sigma](I)

  • Rint = 0.088

Refinement
  • R[F2 > 2[sigma](F2)] = 0.091

  • wR(F2) = 0.227

  • S = 1.13

  • 2210 reflections

  • 109 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.85 e Å-3

  • [Delta][rho]min = -0.93 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2A...O1i 0.82 1.82 2.641 (11) 176
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SADABS, SAINT and SMART. 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2208 ).


Acknowledgements

This work was supported by the National Science Council (NSC 99-2113-M-035-001-MY2) and Feng Chia University, Taiwan.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Dey, S. & Mal, D. (2005). Tetrahedron Lett. 46, 5483-5486.  [ISI] [CrossRef] [ChemPort]
Eliel, E. L. & Rivard, D. E. (1952). J. Org. Chem. 17, 1252-1256.  [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o109  [ doi:10.1107/S1600536811052858 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.