1,2-Bis(dibromo­meth­yl)benzene

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

doi:10.1107/S1600536811050616

Volume 68
Part 1
Page o5
January 2012

Received 29 September 2011
Accepted 25 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.025 Å
R = 0.091
wR = 0.258
Data-to-parameter ratio = 22.7
Details

1,2-Bis(dibromomethyl)benzene

Sin-Kai Fang,^a Hong-Yi Lin ^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 title compound, C₈H₆Br₄, intramolecular C-HBr hydrogen bonds generate two S(6) rings. The two geminal bromine-atom substituents point to opposite sides of the aromatic ring system. In the crystal, molecules are linked by intermolecular [pi] - [pi] interactions with centroid-centroid distances of 3.727 (9) and 3.858 (9) Å.

Related literature

For the preparation of the title compound, see: Ghorbani-Vaghei et al. (2009). For its applications, see: Chen et al. (2002, 2006, 2007); Chow et al. (2005); Jansen et al. (2010); Pandithavidana et al. (2009); Swartz et al. (2005). For related structures, see: Kus & Jones (2003); Qin et al. (2005); Sim et al. (2001). For graph-set theory, see: Bernstein et al. (1995).

Experimental

Crystal data

C₈H₆Br₄
M_r = 421.77
Triclinic, $[P \overline 1]$
a = 7.0222 (8) Å
b = 7.7313 (9) Å
c = 10.5927 (12) Å
= 108.473 (10)°
= 97.108 (9)°
= 90.394 (9)°
V = 540.61 (11) Å³
Z = 2
Mo K radiation
= 14.83 mm^-1
T = 297 K
0.58 × 0.48 × 0.36 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.122, T_max = 1.000
4575 measured reflections
2469 independent reflections
1297 reflections with I > 2(I)
R_int = 0.073

Refinement

R[F² > 2(F²)] = 0.091
wR(F²) = 0.258
S = 1.04
2469 reflections
109 parameters
H-atom parameters constrained
_max = 1.62 e Å^-3
_min = -1.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8ABr1	0.98	2.64	3.364 (16)	131
C8-H8ABr2	0.98	2.78	3.420 (16)	124

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: AA2031 ).

Acknowledgements

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

References

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organic compounds