2-(Dibromo­meth­yl)benzoic acid

Lin, H.-Y.; Fang, S.-K.; Chen, K.-Y.

doi:10.1107/S1600536811052858

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 (C-C) = 0.014 Å
R = 0.091
wR = 0.227
Data-to-parameter ratio = 20.3
Details

2-(Dibromomethyl)benzoic acid

Hong-Yi Lin,^a Sin-Kai Fang ^a and Kew-Yu Chen ^a ^*

^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-HO hydrogen bonds, which link the molecules into inversion dimers.

Related literature

For the preparation of the title compound, see: Eliel & Rivard (1952). For its applications, see: Dey & Mal (2005). For graph-set theory, see: Bernstein et al. (1995).

Experimental

Crystal data

C₈H₆Br₂O₂
M_r = 293.95
Monoclinic, P 2₁ /n
a = 4.9988 (6) Å
b = 25.617 (3) Å
c = 7.1844 (8) Å
= 97.709 (10)°
V = 911.68 (18) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.251, T_max = 1.000
7515 measured reflections
2210 independent reflections
1221 reflections with I > 2(I)
R_int = 0.088

Refinement

R[F² > 2(F²)] = 0.091
wR(F²) = 0.227
S = 1.13
2210 reflections
109 parameters
H-atom parameters constrained
_max = 0.85 e Å^-3
_min = -0.93 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO1ⁱ	0.82	1.82	2.641 (11)	176
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

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.
Bruker (2001). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Dey, S. & Mal, D. (2005). Tetrahedron Lett. 46, 5483-5486.
Eliel, E. L. & Rivard, D. E. (1952). J. Org. Chem. 17, 1252-1256.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds