1,5-Dibromo-2,4-dimeth-oxy-benzene.

In the title compound, C8H8Br2O2, all non-H atoms lie essentially in a common plane (r.m.s deviation of all fitted non-H atoms = 0.0330 Å). In the crystal, weak C-H⋯O hydrogen bonds connect the mol-ecules, forming chains which extend along the b-axis direction.

Related literature

For background to the pharmacological importance of the title compound, see: Pahari & Rohr (2009 ▶). For the synthesis of the title compound, see: Yang et al. (2009 ▶). For a report listing the crystal structure of 1-bromo-5-chloro-2,4-dimeth­oxy­benzene but entered incorrectly as the title compound in the CSD (TASBAR), see: Yang et al. (2005 ▶). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H8Br2O2

M = 295.96

Monoclinic,

a = 7.7944 (2) Å

b = 8.5884 (4) Å

c = 14.7877 (4) Å

β = 107.838 (1)°

V = 942.32 (6) Å3

Z = 4

Mo Kα radiation

μ = 8.56 mm−1

T = 200 K

0.47 × 0.46 × 0.34 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.674, T max = 1.000

15097 measured reflections

2350 independent reflections

2094 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.049

S = 1.08

2350 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); 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 (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047848/zs2243sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047848/zs2243Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047848/zs2243Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047848/zs2243Isup4.cml

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

C8H8Br2O2	F(000) = 568
Mr = 295.96	Dx = 2.086 Mg m−3
Monoclinic, P21/c	Melting point = 414–413 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.7944 (2) Å	Cell parameters from 9980 reflections
b = 8.5884 (4) Å	θ = 2.7–28.3°
c = 14.7877 (4) Å	µ = 8.56 mm−1
β = 107.838 (1)°	T = 200 K
V = 942.32 (6) Å3	Block, white
Z = 4	0.47 × 0.46 × 0.34 mm

Bruker APEXII CCD diffractometer	2350 independent reflections
Radiation source: fine-focus sealed tube	2094 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 28.4°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.674, Tmax = 1.000	k = −11→11
15097 measured reflections	l = −18→19

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0199P)2 + 0.5315P] where P = (Fo2 + 2Fc2)/3
2350 reflections	(Δ/σ)max = 0.001
111 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.43964 (3)	0.63810 (3)	0.268745 (16)	0.04029 (7)
Br2	0.29505 (3)	0.26527 (3)	−0.060701 (15)	0.03453 (7)
O1	0.07656 (18)	0.52208 (17)	0.26640 (10)	0.0321 (3)
O2	−0.04398 (17)	0.19995 (17)	−0.01445 (10)	0.0323 (3)
C1	0.2839 (2)	0.5013 (2)	0.18080 (13)	0.0256 (4)
C2	0.3359 (2)	0.4436 (2)	0.10619 (13)	0.0265 (4)
H2	0.4487	0.4729	0.0992	0.032*
C3	0.2236 (2)	0.3432 (2)	0.04159 (13)	0.0243 (4)
C4	0.0576 (2)	0.2998 (2)	0.05093 (13)	0.0235 (4)
C5	0.0069 (2)	0.3587 (2)	0.12664 (13)	0.0250 (4)
H5	−0.1056	0.3292	0.1339	0.030*
C6	0.1190 (2)	0.4601 (2)	0.19174 (13)	0.0244 (4)
C7	−0.2196 (3)	0.1625 (3)	−0.00979 (15)	0.0338 (4)
H7A	−0.2815	0.0957	−0.0636	0.051*
H7B	−0.2888	0.2585	−0.0123	0.051*
H7C	−0.2089	0.1075	0.0498	0.051*
C8	−0.0860 (3)	0.4691 (3)	0.28213 (15)	0.0340 (4)
H8A	−0.0983	0.5179	0.3397	0.051*
H8B	−0.0816	0.3557	0.2898	0.051*
H8C	−0.1894	0.4976	0.2277	0.051*

	U11	U22	U33	U12	U13	U23
Br1	0.02623 (10)	0.04018 (13)	0.05077 (14)	−0.00833 (8)	0.00632 (9)	−0.01578 (9)
Br2	0.02932 (11)	0.04093 (12)	0.03863 (12)	−0.00448 (8)	0.01823 (9)	−0.00465 (8)
O1	0.0301 (7)	0.0358 (8)	0.0333 (7)	−0.0062 (6)	0.0138 (6)	−0.0083 (6)
O2	0.0238 (7)	0.0400 (8)	0.0353 (7)	−0.0105 (6)	0.0123 (6)	−0.0101 (6)
C1	0.0209 (8)	0.0209 (8)	0.0314 (9)	−0.0031 (6)	0.0026 (7)	−0.0002 (7)
C2	0.0195 (8)	0.0241 (9)	0.0356 (10)	−0.0015 (7)	0.0082 (7)	0.0049 (7)
C3	0.0215 (8)	0.0235 (9)	0.0288 (9)	0.0008 (6)	0.0093 (7)	0.0039 (7)
C4	0.0197 (8)	0.0222 (8)	0.0272 (9)	−0.0012 (7)	0.0053 (7)	0.0030 (7)
C5	0.0195 (8)	0.0257 (9)	0.0309 (9)	−0.0025 (7)	0.0094 (7)	0.0026 (7)
C6	0.0248 (8)	0.0218 (8)	0.0263 (9)	0.0015 (7)	0.0071 (7)	0.0034 (7)
C7	0.0227 (9)	0.0418 (11)	0.0371 (11)	−0.0098 (8)	0.0093 (8)	−0.0034 (9)
C8	0.0336 (10)	0.0397 (11)	0.0328 (10)	−0.0050 (8)	0.0165 (8)	−0.0030 (9)

Br1—C1	1.8918 (18)	C3—C4	1.393 (2)
Br2—C3	1.8873 (19)	C4—C5	1.392 (3)
O1—C6	1.355 (2)	C5—C6	1.391 (3)
O1—C8	1.431 (2)	C5—H5	0.9500
O2—C4	1.352 (2)	C7—H7A	0.9800
O2—C7	1.428 (2)	C7—H7B	0.9800
C1—C2	1.379 (3)	C7—H7C	0.9800
C1—C6	1.389 (2)	C8—H8A	0.9800
C2—C3	1.382 (3)	C8—H8B	0.9800
C2—H2	0.9500	C8—H8C	0.9800
C6—O1—C8	117.21 (15)	C4—C5—H5	119.6
C4—O2—C7	117.93 (15)	O1—C6—C1	117.41 (16)
C2—C1—C6	120.73 (17)	O1—C6—C5	123.47 (16)
C2—C1—Br1	119.28 (13)	C1—C6—C5	119.12 (17)
C6—C1—Br1	119.99 (14)	O2—C7—H7A	109.5
C1—C2—C3	119.87 (17)	O2—C7—H7B	109.5
C1—C2—H2	120.1	H7A—C7—H7B	109.5
C3—C2—H2	120.1	O2—C7—H7C	109.5
C2—C3—C4	120.59 (17)	H7A—C7—H7C	109.5
C2—C3—Br2	119.71 (13)	H7B—C7—H7C	109.5
C4—C3—Br2	119.70 (14)	O1—C8—H8A	109.5
O2—C4—C5	123.84 (16)	O1—C8—H8B	109.5
O2—C4—C3	117.20 (16)	H8A—C8—H8B	109.5
C5—C4—C3	118.96 (16)	O1—C8—H8C	109.5
C6—C5—C4	120.72 (16)	H8A—C8—H8C	109.5
C6—C5—H5	119.6	H8B—C8—H8C	109.5
C6—C1—C2—C3	−0.3 (3)	O2—C4—C5—C6	179.44 (17)
Br1—C1—C2—C3	179.81 (14)	C3—C4—C5—C6	0.5 (3)
C1—C2—C3—C4	0.2 (3)	C8—O1—C6—C1	−174.78 (17)
C1—C2—C3—Br2	179.77 (14)	C8—O1—C6—C5	5.2 (3)
C7—O2—C4—C5	5.2 (3)	C2—C1—C6—O1	−179.57 (17)
C7—O2—C4—C3	−175.84 (17)	Br1—C1—C6—O1	0.3 (2)
C2—C3—C4—O2	−179.34 (16)	C2—C1—C6—C5	0.5 (3)
Br2—C3—C4—O2	1.1 (2)	Br1—C1—C6—C5	−179.65 (13)
C2—C3—C4—C5	−0.3 (3)	C4—C5—C6—O1	179.48 (17)
Br2—C3—C4—C5	−179.86 (13)	C4—C5—C6—C1	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7C···O1i	0.98	2.70	3.632 (3)	160
C1—Br1···Cgii	1.89 (1)	3.75 (1)	5.5701 (19)	161 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7C⋯O1i	0.98	2.70	3.632 (3)	160

Symmetry code: (i) .