1,2-Bis(dibromo-meth-yl)benzene.

In the title compound, C(8)H(6)Br(4), intra-molecular C-H⋯Br 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, mol-ecules are linked by inter-molecular π-π inter-actions 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: Kuś & Jones (2003) ▶; Qin et al. (2005 ▶); Sim et al. (2001 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H6Br4

M = 421.77

Triclinic,

a = 7.0222 (8) Å

b = 7.7313 (9) Å

c = 10.5927 (12) Å

α = 108.473 (10)°

β = 97.108 (9)°

γ = 90.394 (9)°

V = 540.61 (11) Å3

Z = 2

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.091

wR(F 2) = 0.258

S = 1.04

2469 reflections

109 parameters

H-atom parameters constrained

Δρmax = 1.62 e Å−3

Δρmin = −1.27 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811050616/aa2031sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050616/aa2031Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050616/aa2031Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H6Br4	Z = 2
Mr = 421.77	F(000) = 388
Triclinic, P1	Dx = 2.591 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0222 (8) Å	Cell parameters from 1856 reflections
b = 7.7313 (9) Å	θ = 2.8–29.1°
c = 10.5927 (12) Å	µ = 14.83 mm−1
α = 108.473 (10)°	T = 297 K
β = 97.108 (9)°	Parallelepiped, colorless
γ = 90.394 (9)°	0.58 × 0.48 × 0.36 mm
V = 540.61 (11) Å3

Bruker SMART CCD area-detector diffractometer	2469 independent reflections
Radiation source: fine-focus sealed tube	1297 reflections with I > 2σ(I)
graphite	Rint = 0.073
ω scans	θmax = 29.2°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→8
Tmin = 0.122, Tmax = 1.000	k = −10→10
4575 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.091	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.258	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0875P)2 + 18.1246P] where P = (Fo2 + 2Fc2)/3
2469 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 1.62 e Å−3
0 restraints	Δρmin = −1.27 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	1.0868 (3)	0.1807 (3)	0.90582 (19)	0.0434 (6)
Br2	0.6361 (3)	0.1787 (3)	0.9231 (2)	0.0492 (6)
Br3	0.5867 (3)	0.5842 (3)	0.7641 (2)	0.0488 (6)
Br4	1.0292 (3)	0.5783 (3)	0.7275 (2)	0.0478 (6)
C1	0.832 (3)	0.078 (3)	0.8116 (17)	0.036 (4)
H1A	0.8311	−0.0533	0.8003	0.043*
C2	0.796 (2)	0.094 (2)	0.6741 (16)	0.030 (4)
C3	0.769 (2)	−0.070 (3)	0.5681 (18)	0.035 (4)
H3A	0.7804	−0.1803	0.5862	0.042*
C4	0.725 (2)	−0.073 (2)	0.4342 (17)	0.033 (4)
H4A	0.7044	−0.1821	0.3639	0.040*
C5	0.714 (2)	0.097 (3)	0.4101 (16)	0.032 (4)
H5A	0.6924	0.1004	0.3224	0.039*
C6	0.735 (2)	0.255 (2)	0.5136 (16)	0.031 (4)
H6A	0.7183	0.3644	0.4954	0.037*
C7	0.781 (2)	0.261 (2)	0.6455 (15)	0.024 (3)
C8	0.821 (2)	0.436 (2)	0.7532 (17)	0.033 (4)
H8A	0.8533	0.4123	0.8387	0.040*

	U11	U22	U33	U12	U13	U23
Br1	0.0330 (10)	0.0605 (15)	0.0388 (10)	0.0108 (9)	−0.0006 (8)	0.0207 (10)
Br2	0.0364 (11)	0.0769 (17)	0.0443 (11)	0.0028 (10)	0.0117 (9)	0.0313 (11)
Br3	0.0386 (11)	0.0406 (13)	0.0671 (14)	0.0169 (9)	0.0072 (9)	0.0165 (11)
Br4	0.0406 (11)	0.0372 (13)	0.0653 (14)	−0.0084 (8)	0.0102 (9)	0.0148 (10)
C1	0.047 (10)	0.027 (10)	0.041 (10)	−0.009 (8)	0.002 (8)	0.024 (8)
C2	0.019 (7)	0.033 (11)	0.033 (9)	0.003 (7)	0.000 (6)	0.008 (8)
C3	0.016 (8)	0.038 (11)	0.051 (11)	0.004 (7)	0.006 (7)	0.014 (9)
C4	0.040 (10)	0.026 (10)	0.033 (9)	0.005 (7)	0.017 (8)	0.003 (8)
C5	0.024 (8)	0.042 (11)	0.025 (8)	0.015 (7)	0.008 (7)	−0.001 (8)
C6	0.042 (10)	0.015 (9)	0.029 (8)	0.006 (7)	0.009 (7)	−0.003 (7)
C7	0.019 (7)	0.026 (9)	0.032 (8)	0.003 (6)	0.007 (6)	0.013 (7)
C8	0.032 (9)	0.030 (11)	0.038 (9)	−0.011 (7)	0.003 (7)	0.014 (8)

Br1—C1	1.965 (17)	C3—H3A	0.9300
Br2—C1	1.932 (19)	C4—C5	1.42 (3)
Br3—C8	2.003 (18)	C4—H4A	0.9300
Br4—C8	1.922 (15)	C5—C6	1.35 (2)
C1—C2	1.49 (2)	C5—H5A	0.9300
C1—H1A	0.9800	C6—C7	1.38 (2)
C2—C7	1.42 (2)	C6—H6A	0.9300
C2—C3	1.40 (2)	C7—C8	1.47 (2)
C3—C4	1.41 (2)	C8—H8A	0.9800
C2—C1—Br2	113.8 (12)	C6—C5—C4	120.4 (16)
C2—C1—Br1	112.7 (11)	C6—C5—H5A	119.8
Br2—C1—Br1	110.0 (9)	C4—C5—H5A	119.8
C2—C1—H1A	106.6	C5—C6—C7	122.7 (17)
Br2—C1—H1A	106.6	C5—C6—H6A	118.6
Br1—C1—H1A	106.6	C7—C6—H6A	118.6
C7—C2—C3	119.0 (16)	C6—C7—C2	118.7 (15)
C7—C2—C1	124.9 (15)	C6—C7—C8	120.6 (15)
C3—C2—C1	116.0 (16)	C2—C7—C8	120.7 (14)
C4—C3—C2	121.2 (17)	C7—C8—Br4	112.8 (11)
C4—C3—H3A	119.4	C7—C8—Br3	110.0 (11)
C2—C3—H3A	119.4	Br4—C8—Br3	108.1 (9)
C5—C4—C3	117.9 (16)	C7—C8—H8A	108.6
C5—C4—H4A	121.1	Br4—C8—H8A	108.6
C3—C4—H4A	121.1	Br3—C8—H8A	108.6
Br2—C1—C2—C7	61.2 (18)	C5—C6—C7—C8	174.1 (15)
Br1—C1—C2—C7	−65.0 (19)	C3—C2—C7—C6	2(2)
Br2—C1—C2—C3	−117.0 (14)	C1—C2—C7—C6	−176.1 (15)
Br1—C1—C2—C3	116.9 (14)	C3—C2—C7—C8	−175.9 (14)
C7—C2—C3—C4	−1(2)	C1—C2—C7—C8	6(2)
C1—C2—C3—C4	177.2 (14)	C6—C7—C8—Br4	−58.1 (18)
C2—C3—C4—C5	2(2)	C2—C7—C8—Br4	119.7 (14)
C3—C4—C5—C6	−3(2)	C6—C7—C8—Br3	62.6 (16)
C4—C5—C6—C7	5(3)	C2—C7—C8—Br3	−119.6 (13)
C5—C6—C7—C2	−4(2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Br1	0.98	2.64	3.364 (16)	131
C8—H8A···Br2	0.98	2.78	3.420 (16)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯Br1	0.98	2.64	3.364 (16)	131
C8—H8A⋯Br2	0.98	2.78	3.420 (16)	124