1-Bromo-2,3,6-trichloro-4,5-dimethoxy-benzene.

The halogen atoms of the title compound, C(8)H(6)BrCl(3)O(2), are located within the plane of the benzene ring [r.m.s. deviation = 0.036 (11) Å]. The two meth-oxy groups are twisted out of this plane, with dihedral angles of 84.7 (3) and 68.5 (3)°, and point in opposite directions. The structure is disordered by a non-crystallographic twofold rotation which superimposes Cl and Br at two of the halogen sites. The refined occupancies for the major and minor components are 0.517 (2) and 0.483 (2).

Related literature

For similar structures of halogenated meth­oxy benzenes, see: Iimura et al. (1984 ▶); Rissanen et al. (1987 ▶, 1988a ▶,b ▶); Song et al. (2008 ▶, 2010 ▶); Telu et al. (2008 ▶); Weller & Gerstner (1995 ▶); Wieczorek (1980 ▶). For background to halogenated meth­oxy benzenes, see: Brownlee et al. (1993 ▶); Curtis et al. (1972 ▶); Pereira et al. (2000 ▶); Vlachos et al. (2007 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

C8H6BrCl3O2

M = 320.39

Triclinic,

a = 7.7885 (7) Å

b = 8.8600 (7) Å

c = 9.1523 (8) Å

α = 62.256 (3)°

β = 75.358 (4)°

γ = 75.133 (4)°

V = 533.64 (8) Å3

Z = 2

Cu Kα radiation

μ = 11.94 mm−1

T = 90 K

0.20 × 0.15 × 0.07 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.193, T max = 0.434

6588 measured reflections

1828 independent reflections

1720 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.12

1828 reflections

138 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810002977/om2317sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002977/om2317Isup2.hkl

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

C8H6BrCl3O2	Z = 2
Mr = 320.39	F(000) = 312
Triclinic, P1	Dx = 1.994 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.7885 (7) Å	Cell parameters from 5684 reflections
b = 8.8600 (7) Å	θ = 5.5–66.1°
c = 9.1523 (8) Å	µ = 11.94 mm−1
α = 62.256 (3)°	T = 90 K
β = 75.358 (4)°	Irregular plate, colourless
γ = 75.133 (4)°	0.20 × 0.15 × 0.07 mm
V = 533.64 (8) Å3

Bruker X8 Proteum diffractometer	1828 independent reflections
Radiation source: fine-focus rotating anode	1720 reflections with I > 2σ(I)
graded multilayer optics	Rint = 0.038
Detector resolution: 18 pixels mm-1	θmax = 67.4°, θmin = 5.5°
φ and ω scans	h = −9→7
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −10→10
Tmin = 0.193, Tmax = 0.434	l = −10→10
6588 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.726P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.004
1828 reflections	Δρmax = 0.35 e Å−3
138 parameters	Δρmin = −0.52 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0232 (18)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 2σ(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	Occ. (<1)
C1	0.2391 (4)	0.6704 (4)	0.7165 (4)	0.0318 (6)
C2	0.2512 (4)	0.7913 (5)	0.7681 (4)	0.0360 (7)
C3	0.2598 (4)	0.9603 (4)	0.6519 (4)	0.0356 (7)
C4	0.2536 (4)	1.0107 (4)	0.4851 (4)	0.0366 (7)
C5	0.2393 (4)	0.8899 (4)	0.4345 (4)	0.0350 (7)
C6	0.2314 (4)	0.7212 (4)	0.5504 (4)	0.0329 (7)
O1	0.2295 (3)	0.5051 (3)	0.8291 (3)	0.0418 (6)
C7	0.3984 (6)	0.3991 (5)	0.8622 (6)	0.0592 (11)
H7A	0.4694	0.3956	0.7585	0.089*
H7B	0.3800	0.2818	0.9444	0.089*
H7C	0.4627	0.4464	0.9066	0.089*
O2	0.2646 (3)	0.7442 (4)	0.9285 (3)	0.0486 (6)
C8	0.1070 (5)	0.6975 (6)	1.0458 (5)	0.0558 (10)
H8A	0.0096	0.7968	1.0188	0.084*
H8B	0.1309	0.6619	1.1584	0.084*
H8C	0.0717	0.6014	1.0412	0.084*
Cl1	0.27710 (13)	1.10613 (13)	0.71869 (14)	0.0567 (3)
Cl2	0.265 (3)	1.2206 (17)	0.326 (2)	0.0539 (7)	0.483 (3)
Br3	0.2388 (9)	0.9427 (6)	0.2147 (7)	0.0495 (7)	0.483 (3)
Br2	0.2599 (11)	1.2383 (6)	0.3376 (8)	0.0539 (7)	0.517 (3)
Cl3	0.228 (2)	0.9701 (14)	0.2211 (15)	0.0495 (7)	0.517 (3)
Cl4	0.20968 (13)	0.56783 (11)	0.49546 (11)	0.0485 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0236 (14)	0.0338 (16)	0.0354 (16)	−0.0092 (12)	−0.0006 (11)	−0.0123 (13)
C2	0.0257 (15)	0.0442 (18)	0.0406 (17)	−0.0106 (13)	0.0000 (12)	−0.0203 (15)
C3	0.0255 (15)	0.0388 (17)	0.0513 (19)	−0.0071 (12)	−0.0013 (13)	−0.0280 (15)
C4	0.0242 (15)	0.0279 (15)	0.0501 (19)	−0.0039 (12)	0.0005 (13)	−0.0136 (14)
C5	0.0269 (15)	0.0348 (16)	0.0392 (16)	−0.0046 (12)	−0.0039 (12)	−0.0133 (14)
C6	0.0291 (15)	0.0323 (16)	0.0387 (16)	−0.0080 (12)	−0.0021 (12)	−0.0163 (13)
O1	0.0424 (13)	0.0343 (12)	0.0402 (12)	−0.0132 (10)	−0.0033 (10)	−0.0072 (10)
C7	0.054 (2)	0.040 (2)	0.060 (2)	0.0007 (17)	−0.0095 (19)	−0.0062 (18)
O2	0.0456 (14)	0.0687 (17)	0.0418 (13)	−0.0189 (12)	−0.0064 (10)	−0.0275 (13)
C8	0.050 (2)	0.076 (3)	0.0380 (19)	−0.009 (2)	−0.0024 (16)	−0.0245 (19)
Cl1	0.0559 (6)	0.0536 (6)	0.0797 (7)	−0.0177 (4)	0.0007 (5)	−0.0454 (5)
Cl2	0.0526 (6)	0.0296 (11)	0.0692 (11)	−0.0075 (10)	−0.0009 (7)	−0.0165 (7)
Br3	0.0579 (9)	0.0403 (16)	0.0456 (6)	−0.0037 (12)	−0.0149 (5)	−0.0133 (8)
Br2	0.0526 (6)	0.0296 (11)	0.0692 (11)	−0.0075 (10)	−0.0009 (7)	−0.0165 (7)
Cl3	0.0579 (9)	0.0403 (16)	0.0456 (6)	−0.0037 (12)	−0.0149 (5)	−0.0133 (8)
Cl4	0.0670 (6)	0.0407 (5)	0.0471 (5)	−0.0185 (4)	−0.0078 (4)	−0.0221 (4)

C1—O1	1.351 (4)	C5—Cl3	1.758 (12)
C1—C6	1.383 (5)	C5—Br3	1.842 (6)
C1—C2	1.388 (5)	C6—Cl4	1.710 (3)
C2—O2	1.350 (4)	O1—C7	1.417 (5)
C2—C3	1.382 (5)	C7—H7A	0.9800
C3—C4	1.387 (5)	C7—H7B	0.9800
C3—Cl1	1.711 (3)	C7—H7C	0.9800
C4—C5	1.386 (5)	O2—C8	1.418 (5)
C4—Cl2	1.756 (15)	C8—H8A	0.9800
C4—Br2	1.837 (6)	C8—H8B	0.9800
C5—C6	1.379 (5)	C8—H8C	0.9800
O1—C1—C6	120.3 (3)	C4—C5—Br3	122.6 (3)
O1—C1—C2	120.0 (3)	C5—C6—C1	120.8 (3)
C6—C1—C2	119.7 (3)	C5—C6—Cl4	121.6 (3)
O2—C2—C3	119.5 (3)	C1—C6—Cl4	117.6 (2)
O2—C2—C1	120.9 (3)	C1—O1—C7	114.5 (3)
C3—C2—C1	119.5 (3)	O1—C7—H7A	109.5
C2—C3—C4	120.7 (3)	O1—C7—H7B	109.5
C2—C3—Cl1	118.5 (3)	H7A—C7—H7B	109.5
C4—C3—Cl1	120.8 (3)	O1—C7—H7C	109.5
C5—C4—C3	119.5 (3)	H7A—C7—H7C	109.5
C5—C4—Cl2	115.5 (6)	H7B—C7—H7C	109.5
C3—C4—Cl2	125.0 (7)	C2—O2—C8	115.4 (3)
C5—C4—Br2	121.8 (3)	O2—C8—H8A	109.5
C3—C4—Br2	118.7 (3)	O2—C8—H8B	109.5
C6—C5—C4	119.7 (3)	H8A—C8—H8B	109.5
C6—C5—Cl3	125.0 (5)	O2—C8—H8C	109.5
C4—C5—Cl3	115.3 (4)	H8A—C8—H8C	109.5
C6—C5—Br3	117.6 (3)	H8B—C8—H8C	109.5
O1—C1—C2—O2	4.0 (5)	Br2—C4—C5—Cl3	0.1 (7)
C6—C1—C2—O2	−177.9 (3)	C3—C4—C5—Br3	−177.6 (3)
O1—C1—C2—C3	−179.6 (3)	Cl2—C4—C5—Br3	1.8 (9)
C6—C1—C2—C3	−1.5 (5)	Br2—C4—C5—Br3	3.7 (5)
O2—C2—C3—C4	177.4 (3)	C4—C5—C6—C1	−0.6 (5)
C1—C2—C3—C4	1.0 (5)	Cl3—C5—C6—C1	−179.2 (7)
O2—C2—C3—Cl1	−2.9 (4)	Br3—C5—C6—C1	177.2 (3)
C1—C2—C3—Cl1	−179.3 (2)	C4—C5—C6—Cl4	178.8 (2)
C2—C3—C4—C5	−0.3 (5)	Cl3—C5—C6—Cl4	0.2 (8)
Cl1—C3—C4—C5	−179.9 (2)	Br3—C5—C6—Cl4	−3.4 (4)
C2—C3—C4—Cl2	−179.6 (9)	O1—C1—C6—C5	179.4 (3)
Cl1—C3—C4—Cl2	0.7 (10)	C2—C1—C6—C5	1.3 (5)
C2—C3—C4—Br2	178.5 (4)	O1—C1—C6—Cl4	0.0 (4)
Cl1—C3—C4—Br2	−1.2 (5)	C2—C1—C6—Cl4	−178.1 (2)
C3—C4—C5—C6	0.0 (5)	C6—C1—O1—C7	96.2 (4)
Cl2—C4—C5—C6	179.4 (8)	C2—C1—O1—C7	−85.7 (4)
Br2—C4—C5—C6	−178.7 (4)	C3—C2—O2—C8	113.2 (4)
C3—C4—C5—Cl3	178.8 (6)	C1—C2—O2—C8	−70.5 (4)
Cl2—C4—C5—Cl3	−1.8 (10)