1-Bromo-2-chloro-4,5-dimethoxy-benzene.

The two meth-oxy groups of the title compound, C(8)H(8)BrClO(2), are approximately coplanar with the benzene ring, the dihedral angles in all four mol-ecules in the asymmetric unit ranging from of 0.9 (3) to 12.3 (3)°. All four independent mol-ecules are disordered by different amounts about non-crystallographic twofold axes which nearly superimpose the Cl and Br sites.

Related literature

For similar structures of halogenated meth­oxy benzenes, see: Iimura et al. (1984 ▶); Rissanen et al. (1987 ▶, 1988a ▶,b ▶); Song et al. (2008 ▶, 2010a ▶,b ▶); Telu et al. (2008 ▶); Weller & Gerstner (1995 ▶); Wieczorek (1980 ▶). For general background to halogenated meth­oxy benzenes, see: Ballschmiter, (2003 ▶); Brownlee et al. (1993 ▶); Curtis et al. (1972 ▶); Pereira et al. (2000 ▶); Vlachos et al. (2007 ▶).

Experimental

Crystal data

C8H8BrClO2

M = 251.50

Triclinic,

a = 9.9264 (2) Å

b = 9.9410 (2) Å

c = 19.7219 (5) Å

α = 75.9259 (8)°

β = 75.9323 (8)°

γ = 79.9479 (10)°

V = 1817.26 (7) Å3

Z = 8

Mo Kα radiation

μ = 4.77 mm−1

T = 90 K

0.22 × 0.22 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.360, T max = 0.385

14754 measured reflections

8202 independent reflections

6065 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.070

S = 1.04

8202 reflections

471 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.42 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); 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/S1600536810008445/ci5050sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008445/ci5050Isup2.hkl

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

C8H8BrClO2	Z = 8
Mr = 251.50	F(000) = 992
Triclinic, P1	Dx = 1.839 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9264 (2) Å	Cell parameters from 7193 reflections
b = 9.9410 (2) Å	θ = 1.0–27.5°
c = 19.7219 (5) Å	µ = 4.77 mm−1
α = 75.9259 (8)°	T = 90 K
β = 75.9323 (8)°	Block, colourless
γ = 79.9479 (10)°	0.22 × 0.22 × 0.20 mm
V = 1817.26 (7) Å3

Nonius KappaCCD diffractometer	8202 independent reflections
Radiation source: fine-focus sealed tube	6065 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 18 pixels mm-1	θmax = 27.5°, θmin = 2.1°
ω scans at fixed χ = 55°	h = −12→12
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.360, Tmax = 0.385	l = −25→25
14754 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0154P)2 + 1.1857P] where P = (Fo2 + 2Fc2)/3
8202 reflections	(Δ/σ)max = 0.004
471 parameters	Δρmax = 0.43 e Å−3
16 restraints	Δρmin = −0.41 e Å−3

Experimental. The triclinic cell appears to transform to a C-centered monoclinic cell but the data fail to merge in a satisfactory way in that setting. The structure solved and refined well with the triclinic setting in spite of the extensive disorder. The refined model does not transform to any monoclinic C model either manually or by use of missed symmetry algorithms such as ADDSYM as implemented in Platon (Spek).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
Br1A	−0.0045 (2)	0.9524 (3)	0.89744 (16)	0.0246 (2)	0.7451 (15)
Cl1A	0.0944 (17)	0.6347 (17)	0.9666 (8)	0.0225 (9)	0.7451 (15)
Br1E	0.096 (2)	0.618 (2)	0.9722 (9)	0.0225 (9)	0.2549 (15)
Cl1E	0.0103 (17)	0.954 (2)	0.8902 (13)	0.0246 (2)	0.2549 (15)
O1A	0.54879 (19)	0.65270 (19)	0.77345 (10)	0.0217 (5)
O2A	0.47578 (19)	0.90927 (19)	0.71339 (10)	0.0228 (5)
C1A	0.1671 (3)	0.8534 (3)	0.85998 (15)	0.0192 (6)
C2A	0.2065 (3)	0.7175 (3)	0.89182 (14)	0.0177 (6)
C3A	0.3335 (3)	0.6477 (3)	0.86393 (15)	0.0177 (6)
H3A	0.3599	0.5538	0.8860	0.021*
C4A	0.4218 (3)	0.7129 (3)	0.80463 (15)	0.0177 (6)
C5A	0.3819 (3)	0.8520 (3)	0.77156 (15)	0.0189 (6)
C6A	0.2548 (3)	0.9211 (3)	0.79966 (15)	0.0194 (6)
H6A	0.2273	1.0148	0.7777	0.023*
C7A	0.5938 (3)	0.5126 (3)	0.80712 (16)	0.0214 (7)
H7A1	0.6038	0.5111	0.8555	0.032*
H7A2	0.6841	0.4794	0.7792	0.032*
H7A3	0.5243	0.4517	0.8096	0.032*
C8A	0.4342 (3)	1.0479 (3)	0.67626 (16)	0.0249 (7)
H8A1	0.3468	1.0494	0.6611	0.037*
H8A2	0.5076	1.0756	0.6341	0.037*
H8A3	0.4200	1.1132	0.7081	0.037*
Br1B	0.4007 (8)	0.3438 (5)	1.0251 (4)	0.0247 (4)	0.5438 (15)
Cl1B	0.698 (2)	0.2075 (19)	0.9410 (8)	0.0245 (6)	0.5438 (15)
Br1F	0.7056 (10)	0.2212 (9)	0.9393 (4)	0.0245 (6)	0.4562 (15)
Cl1F	0.400 (2)	0.3317 (15)	1.0310 (12)	0.0247 (4)	0.4562 (15)
O1B	0.41582 (19)	−0.1413 (2)	1.20683 (10)	0.0233 (5)
O2B	0.65841 (19)	−0.23454 (19)	1.14057 (10)	0.0219 (5)
C1B	0.6106 (3)	0.1110 (3)	1.02176 (14)	0.0182 (6)
C2B	0.4826 (3)	0.1619 (3)	1.05831 (15)	0.0186 (6)
C3B	0.4143 (3)	0.0807 (3)	1.12061 (15)	0.0201 (6)
H3B	0.3263	0.1169	1.1455	0.024*
C4B	0.4733 (3)	−0.0519 (3)	1.14657 (15)	0.0168 (6)
C5B	0.6059 (3)	−0.1041 (3)	1.10984 (15)	0.0170 (6)
C6B	0.6721 (3)	−0.0233 (3)	1.04787 (15)	0.0175 (6)
H6B	0.7602	−0.0588	1.0227	0.021*
C7B	0.2835 (3)	−0.0911 (3)	1.24616 (16)	0.0291 (7)
H7B1	0.2936	−0.0102	1.2639	0.044*
H7B2	0.2503	−0.1652	1.2867	0.044*
H7B3	0.2159	−0.0635	1.2149	0.044*
C8B	0.7944 (3)	−0.2893 (3)	1.10553 (16)	0.0247 (7)
H8B1	0.7907	−0.2980	1.0576	0.037*
H8B2	0.8227	−0.3815	1.1334	0.037*
H8B3	0.8624	−0.2259	1.1017	0.037*
Br1C	1.2543 (5)	0.6563 (7)	0.4287 (3)	0.0254 (4)	0.5027 (15)
Cl1C	1.3717 (15)	0.357 (2)	0.5194 (12)	0.0222 (4)	0.5027 (15)
Br1G	1.3817 (6)	0.3453 (8)	0.5159 (5)	0.0222 (4)	0.4973 (15)
Cl1G	1.2350 (13)	0.6548 (19)	0.4322 (7)	0.0254 (4)	0.4973 (15)
O1C	0.83249 (19)	0.63322 (19)	0.65073 (10)	0.0217 (5)
O2C	0.9333 (2)	0.3954 (2)	0.71708 (10)	0.0233 (5)
C1C	1.2099 (3)	0.4433 (3)	0.55384 (15)	0.0174 (6)
C2C	1.1566 (3)	0.5695 (3)	0.51819 (14)	0.0186 (6)
C3C	1.0281 (3)	0.6376 (3)	0.54883 (14)	0.0176 (6)
H3C	0.9909	0.7250	0.5238	0.021*
C4C	0.9560 (3)	0.5771 (3)	0.61543 (15)	0.0189 (6)
C5C	1.0120 (3)	0.4465 (3)	0.65207 (15)	0.0176 (6)
C6C	1.1377 (3)	0.3812 (3)	0.62102 (15)	0.0186 (6)
H6C	1.1755	0.2935	0.6454	0.022*
C7C	0.7725 (3)	0.7672 (3)	0.61599 (16)	0.0259 (7)
H7C1	0.8364	0.8367	0.6087	0.039*
H7C2	0.6828	0.7955	0.6460	0.039*
H7C3	0.7576	0.7605	0.5696	0.039*
C8C	0.9994 (3)	0.2797 (3)	0.76102 (16)	0.0252 (7)
H8C1	1.0156	0.1976	0.7396	0.038*
H8C2	0.9389	0.2598	0.8087	0.038*
H8C3	1.0891	0.3023	0.7650	0.038*
Br1D	0.9822 (6)	0.9422 (4)	0.3907 (3)	0.0248 (3)	0.6246 (15)
Cl1D	0.667 (2)	1.065 (2)	0.4698 (8)	0.0265 (8)	0.6246 (15)
Br1H	0.6728 (14)	1.0541 (14)	0.4769 (5)	0.0265 (8)	0.3754 (15)
Cl1H	0.978 (2)	0.9528 (16)	0.3837 (11)	0.0248 (3)	0.3754 (15)
O1D	0.94378 (19)	1.42221 (19)	0.20683 (10)	0.0199 (4)
O2D	0.69740 (19)	1.50728 (19)	0.27335 (10)	0.0196 (4)
C1D	0.7583 (3)	1.1643 (3)	0.39183 (14)	0.0203 (7)
C2D	0.8882 (3)	1.1176 (3)	0.35572 (15)	0.0190 (6)
C3D	0.9541 (3)	1.2016 (3)	0.29312 (15)	0.0179 (6)
H3D	1.0442	1.1693	0.2686	0.022*
C4D	0.8889 (3)	1.3311 (3)	0.26678 (15)	0.0181 (6)
C5D	0.7543 (3)	1.3787 (3)	0.30347 (15)	0.0170 (6)
C6D	0.6913 (3)	1.2950 (3)	0.36545 (15)	0.0198 (6)
H6D	0.6013	1.3266	0.3904	0.024*
C7D	1.0845 (3)	1.3829 (3)	0.17138 (16)	0.0238 (7)
H7D1	1.1459	1.3604	0.2057	0.036*
H7D2	1.1163	1.4606	0.1327	0.036*
H7D3	1.0873	1.3009	0.1515	0.036*
C8D	0.5633 (3)	1.5601 (3)	0.31173 (16)	0.0234 (7)
H8D1	0.4954	1.4951	0.3178	0.035*
H8D2	0.5312	1.6517	0.2847	0.035*
H8D3	0.5721	1.5693	0.3588	0.035*

	U11	U22	U33	U12	U13	U23
Br1A	0.0207 (6)	0.0204 (2)	0.0261 (8)	0.0010 (4)	0.0031 (4)	−0.0028 (4)
Cl1A	0.0260 (4)	0.016 (3)	0.0187 (17)	−0.0060 (16)	0.0003 (11)	0.0057 (14)
Br1E	0.0260 (4)	0.016 (3)	0.0187 (17)	−0.0060 (16)	0.0003 (11)	0.0057 (14)
Cl1E	0.0207 (6)	0.0204 (2)	0.0261 (8)	0.0010 (4)	0.0031 (4)	−0.0028 (4)
O1A	0.0190 (10)	0.0158 (10)	0.0253 (12)	0.0016 (8)	−0.0008 (9)	−0.0014 (9)
O2A	0.0220 (11)	0.0167 (11)	0.0232 (12)	−0.0037 (9)	0.0010 (9)	0.0032 (9)
C1A	0.0155 (14)	0.0203 (16)	0.0220 (16)	−0.0014 (12)	−0.0018 (12)	−0.0076 (13)
C2A	0.0204 (15)	0.0179 (15)	0.0162 (15)	−0.0072 (12)	−0.0028 (12)	−0.0037 (12)
C3A	0.0194 (15)	0.0141 (14)	0.0191 (16)	−0.0012 (12)	−0.0043 (12)	−0.0027 (12)
C4A	0.0162 (14)	0.0178 (15)	0.0212 (16)	−0.0025 (12)	−0.0044 (12)	−0.0070 (13)
C5A	0.0198 (15)	0.0190 (15)	0.0201 (16)	−0.0076 (12)	−0.0044 (13)	−0.0043 (13)
C6A	0.0217 (15)	0.0144 (15)	0.0222 (17)	−0.0029 (12)	−0.0048 (13)	−0.0036 (13)
C7A	0.0196 (15)	0.0186 (16)	0.0242 (17)	0.0010 (12)	−0.0055 (13)	−0.0024 (13)
C8A	0.0261 (17)	0.0180 (16)	0.0255 (18)	−0.0037 (13)	−0.0023 (14)	0.0027 (13)
Br1B	0.0320 (3)	0.0169 (9)	0.0225 (13)	0.0032 (7)	−0.0081 (7)	−0.0010 (7)
Cl1B	0.0267 (11)	0.0222 (16)	0.0212 (4)	−0.0091 (8)	−0.0005 (4)	0.0016 (7)
Br1F	0.0267 (11)	0.0222 (16)	0.0212 (4)	−0.0091 (8)	−0.0005 (4)	0.0016 (7)
Cl1F	0.0320 (3)	0.0169 (9)	0.0225 (13)	0.0032 (7)	−0.0081 (7)	−0.0010 (7)
O1B	0.0211 (11)	0.0248 (11)	0.0158 (11)	−0.0012 (9)	0.0018 (9)	0.0041 (9)
O2B	0.0227 (11)	0.0192 (11)	0.0184 (11)	0.0016 (9)	−0.0020 (9)	0.0006 (9)
C1B	0.0216 (15)	0.0193 (15)	0.0156 (15)	−0.0079 (12)	−0.0036 (12)	−0.0037 (12)
C2B	0.0220 (15)	0.0133 (14)	0.0224 (16)	−0.0013 (12)	−0.0099 (13)	−0.0027 (12)
C3B	0.0198 (15)	0.0223 (16)	0.0177 (16)	−0.0013 (12)	−0.0026 (13)	−0.0054 (13)
C4B	0.0186 (15)	0.0164 (15)	0.0150 (15)	−0.0044 (12)	−0.0026 (12)	−0.0018 (12)
C5B	0.0209 (15)	0.0160 (15)	0.0155 (15)	−0.0003 (12)	−0.0065 (12)	−0.0047 (12)
C6B	0.0174 (15)	0.0182 (15)	0.0173 (15)	−0.0037 (12)	−0.0033 (12)	−0.0034 (12)
C7B	0.0204 (16)	0.0349 (19)	0.0221 (18)	0.0021 (14)	0.0027 (13)	0.0019 (15)
C8B	0.0239 (16)	0.0218 (16)	0.0247 (17)	0.0039 (13)	−0.0021 (14)	−0.0058 (14)
Br1C	0.0183 (14)	0.0303 (3)	0.0202 (6)	−0.0011 (10)	0.0021 (7)	0.0009 (4)
Cl1C	0.0207 (9)	0.0226 (13)	0.0212 (9)	0.0018 (6)	−0.0004 (7)	−0.0075 (7)
Br1G	0.0207 (9)	0.0226 (13)	0.0212 (9)	0.0018 (6)	−0.0004 (7)	−0.0075 (7)
Cl1G	0.0183 (14)	0.0303 (3)	0.0202 (6)	−0.0011 (10)	0.0021 (7)	0.0009 (4)
O1C	0.0188 (10)	0.0202 (11)	0.0204 (11)	0.0029 (8)	0.0000 (9)	−0.0018 (9)
O2C	0.0240 (11)	0.0216 (11)	0.0179 (11)	−0.0002 (9)	0.0002 (9)	0.0016 (9)
C1C	0.0161 (14)	0.0202 (16)	0.0180 (16)	−0.0025 (12)	−0.0034 (12)	−0.0082 (13)
C2C	0.0198 (15)	0.0208 (16)	0.0154 (15)	−0.0059 (13)	−0.0029 (12)	−0.0026 (13)
C3C	0.0208 (15)	0.0150 (15)	0.0172 (16)	−0.0008 (12)	−0.0076 (13)	−0.0012 (12)
C4C	0.0171 (15)	0.0187 (15)	0.0212 (16)	−0.0035 (12)	−0.0021 (13)	−0.0056 (13)
C5C	0.0205 (15)	0.0165 (15)	0.0154 (15)	−0.0050 (12)	−0.0026 (12)	−0.0017 (12)
C6C	0.0228 (16)	0.0108 (14)	0.0222 (16)	−0.0010 (12)	−0.0073 (13)	−0.0017 (12)
C7C	0.0216 (16)	0.0233 (17)	0.0285 (18)	0.0037 (13)	−0.0049 (14)	−0.0025 (14)
C8C	0.0311 (17)	0.0217 (16)	0.0176 (16)	−0.0009 (13)	−0.0044 (14)	0.0034 (13)
Br1D	0.0298 (4)	0.0143 (6)	0.0241 (11)	0.0025 (5)	−0.0030 (6)	0.0014 (6)
Cl1D	0.0316 (9)	0.0224 (18)	0.0174 (17)	−0.0032 (11)	0.0017 (12)	0.0045 (10)
Br1H	0.0316 (9)	0.0224 (18)	0.0174 (17)	−0.0032 (11)	0.0017 (12)	0.0045 (10)
Cl1H	0.0298 (4)	0.0143 (6)	0.0241 (11)	0.0025 (5)	−0.0030 (6)	0.0014 (6)
O1D	0.0181 (10)	0.0182 (10)	0.0186 (11)	−0.0002 (8)	−0.0009 (9)	0.0012 (9)
O2D	0.0205 (11)	0.0156 (10)	0.0197 (11)	0.0017 (8)	−0.0031 (9)	−0.0021 (9)
C1D	0.0252 (16)	0.0177 (15)	0.0170 (16)	−0.0067 (13)	−0.0015 (13)	−0.0019 (13)
C2D	0.0231 (16)	0.0103 (14)	0.0249 (17)	−0.0015 (12)	−0.0085 (13)	−0.0032 (12)
C3D	0.0171 (14)	0.0161 (15)	0.0207 (16)	−0.0006 (12)	−0.0040 (12)	−0.0050 (12)
C4D	0.0215 (15)	0.0198 (16)	0.0137 (15)	−0.0072 (12)	−0.0033 (12)	−0.0018 (12)
C5D	0.0190 (15)	0.0140 (14)	0.0192 (16)	−0.0007 (11)	−0.0072 (12)	−0.0034 (12)
C6D	0.0204 (15)	0.0213 (16)	0.0177 (16)	−0.0030 (12)	−0.0021 (13)	−0.0059 (13)
C7D	0.0197 (16)	0.0231 (16)	0.0234 (17)	−0.0024 (13)	0.0028 (13)	−0.0029 (13)
C8D	0.0207 (16)	0.0224 (16)	0.0268 (18)	0.0050 (13)	−0.0066 (14)	−0.0085 (14)

Br1A—C1A	1.890 (3)	Br1C—C2C	1.877 (5)
Cl1A—C2A	1.739 (8)	Cl1C—C1C	1.746 (10)
Br1E—C2A	1.862 (9)	Br1G—C1C	1.890 (5)
Cl1E—C1A	1.753 (11)	Cl1G—C2C	1.758 (10)
O1A—C4A	1.365 (3)	O1C—C4C	1.354 (3)
O1A—C7A	1.434 (3)	O1C—C7C	1.440 (3)
O2A—C5A	1.362 (3)	O2C—C5C	1.359 (3)
O2A—C8A	1.436 (3)	O2C—C8C	1.425 (3)
C1A—C2A	1.376 (4)	C1C—C2C	1.367 (4)
C1A—C6A	1.392 (4)	C1C—C6C	1.394 (4)
C2A—C3A	1.385 (4)	C2C—C3C	1.405 (4)
C3A—C4A	1.374 (4)	C3C—C4C	1.381 (4)
C3A—H3A	0.95	C3C—H3C	0.95
C4A—C5A	1.411 (4)	C4C—C5C	1.416 (4)
C5A—C6A	1.383 (4)	C5C—C6C	1.375 (4)
C6A—H6A	0.95	C6C—H6C	0.95
C7A—H7A1	0.98	C7C—H7C1	0.98
C7A—H7A2	0.98	C7C—H7C2	0.98
C7A—H7A3	0.98	C7C—H7C3	0.98
C8A—H8A1	0.98	C8C—H8C1	0.98
C8A—H8A2	0.98	C8C—H8C2	0.98
C8A—H8A3	0.98	C8C—H8C3	0.98
Br1B—C2B	1.879 (5)	Br1D—C2D	1.883 (4)
Cl1B—C1B	1.755 (10)	Cl1D—C1D	1.747 (10)
Br1F—C1B	1.867 (6)	Br1H—C1D	1.864 (7)
Cl1F—C2B	1.760 (11)	Cl1H—C2D	1.753 (11)
O1B—C4B	1.364 (3)	O1D—C4D	1.361 (3)
O1B—C7B	1.428 (3)	O1D—C7D	1.435 (3)
O2B—C5B	1.363 (3)	O2D—C5D	1.359 (3)
O2B—C8B	1.439 (3)	O2D—C8D	1.442 (3)
C1B—C2B	1.377 (4)	C1D—C2D	1.375 (4)
C1B—C6B	1.398 (4)	C1D—C6D	1.393 (4)
C2B—C3B	1.387 (4)	C2D—C3D	1.395 (4)
C3B—C4B	1.375 (4)	C3D—C4D	1.375 (4)
C3B—H3B	0.95	C3D—H3D	0.95
C4B—C5B	1.416 (4)	C4D—C5D	1.417 (4)
C5B—C6B	1.374 (4)	C5D—C6D	1.376 (4)
C6B—H6B	0.95	C6D—H6D	0.95
C7B—H7B1	0.98	C7D—H7D1	0.98
C7B—H7B2	0.98	C7D—H7D2	0.98
C7B—H7B3	0.98	C7D—H7D3	0.98
C8B—H8B1	0.98	C8D—H8D1	0.98
C8B—H8B2	0.98	C8D—H8D2	0.98
C8B—H8B3	0.98	C8D—H8D3	0.98
C4A—O1A—C7A	116.8 (2)	C4C—O1C—C7C	117.1 (2)
C5A—O2A—C8A	117.0 (2)	C5C—O2C—C8C	116.2 (2)
C2A—C1A—C6A	120.1 (2)	C2C—C1C—C6C	120.4 (2)
C2A—C1A—Cl1E	124.7 (8)	C2C—C1C—Cl1C	122.0 (8)
C6A—C1A—Cl1E	115.2 (8)	C6C—C1C—Cl1C	117.6 (8)
C2A—C1A—Br1A	121.1 (2)	C2C—C1C—Br1G	122.6 (4)
C6A—C1A—Br1A	118.8 (2)	C6C—C1C—Br1G	117.0 (3)
C1A—C2A—C3A	120.1 (2)	C1C—C2C—C3C	120.2 (2)
C1A—C2A—Cl1A	119.3 (6)	C1C—C2C—Cl1G	124.5 (6)
C3A—C2A—Cl1A	120.7 (6)	C3C—C2C—Cl1G	115.3 (6)
C1A—C2A—Br1E	123.3 (7)	C1C—C2C—Br1C	121.0 (3)
C3A—C2A—Br1E	116.6 (7)	C3C—C2C—Br1C	118.8 (3)
C4A—C3A—C2A	120.7 (3)	C4C—C3C—C2C	119.8 (3)
C4A—C3A—H3A	119.7	C4C—C3C—H3C	120.1
C2A—C3A—H3A	119.7	C2C—C3C—H3C	120.1
O1A—C4A—C3A	124.8 (3)	O1C—C4C—C3C	125.2 (3)
O1A—C4A—C5A	115.6 (2)	O1C—C4C—C5C	115.1 (2)
C3A—C4A—C5A	119.6 (3)	C3C—C4C—C5C	119.6 (3)
O2A—C5A—C6A	124.7 (3)	O2C—C5C—C6C	125.1 (3)
O2A—C5A—C4A	115.9 (2)	O2C—C5C—C4C	115.3 (2)
C6A—C5A—C4A	119.4 (3)	C6C—C5C—C4C	119.7 (3)
C5A—C6A—C1A	120.1 (3)	C5C—C6C—C1C	120.3 (3)
C5A—C6A—H6A	119.9	C5C—C6C—H6C	119.9
C1A—C6A—H6A	119.9	C1C—C6C—H6C	119.9
O1A—C7A—H7A1	109.5	O1C—C7C—H7C1	109.5
O1A—C7A—H7A2	109.5	O1C—C7C—H7C2	109.5
H7A1—C7A—H7A2	109.5	H7C1—C7C—H7C2	109.5
O1A—C7A—H7A3	109.5	O1C—C7C—H7C3	109.5
H7A1—C7A—H7A3	109.5	H7C1—C7C—H7C3	109.5
H7A2—C7A—H7A3	109.5	H7C2—C7C—H7C3	109.5
O2A—C8A—H8A1	109.5	O2C—C8C—H8C1	109.5
O2A—C8A—H8A2	109.5	O2C—C8C—H8C2	109.5
H8A1—C8A—H8A2	109.5	H8C1—C8C—H8C2	109.5
O2A—C8A—H8A3	109.5	O2C—C8C—H8C3	109.5
H8A1—C8A—H8A3	109.5	H8C1—C8C—H8C3	109.5
H8A2—C8A—H8A3	109.5	H8C2—C8C—H8C3	109.5
C4B—O1B—C7B	116.6 (2)	C4D—O1D—C7D	116.8 (2)
C5B—O2B—C8B	116.9 (2)	C5D—O2D—C8D	116.4 (2)
C2B—C1B—C6B	119.7 (2)	C2D—C1D—C6D	120.1 (2)
C2B—C1B—Cl1B	122.0 (8)	C2D—C1D—Cl1D	123.2 (7)
C6B—C1B—Cl1B	118.3 (8)	C6D—C1D—Cl1D	116.7 (7)
C2B—C1B—Br1F	120.8 (4)	C2D—C1D—Br1H	120.1 (5)
C6B—C1B—Br1F	119.5 (4)	C6D—C1D—Br1H	119.8 (5)
C1B—C2B—C3B	120.5 (3)	C1D—C2D—C3D	120.1 (3)
C1B—C2B—Cl1F	122.8 (8)	C1D—C2D—Cl1H	123.1 (8)
C3B—C2B—Cl1F	116.7 (8)	C3D—C2D—Cl1H	116.7 (8)
C1B—C2B—Br1B	120.2 (3)	C1D—C2D—Br1D	121.0 (3)
C3B—C2B—Br1B	119.4 (3)	C3D—C2D—Br1D	118.9 (3)
C4B—C3B—C2B	120.4 (3)	C4D—C3D—C2D	120.2 (3)
C4B—C3B—H3B	119.8	C4D—C3D—H3D	119.9
C2B—C3B—H3B	119.8	C2D—C3D—H3D	119.9
O1B—C4B—C3B	125.6 (3)	O1D—C4D—C3D	125.2 (3)
O1B—C4B—C5B	115.0 (2)	O1D—C4D—C5D	115.1 (2)
C3B—C4B—C5B	119.4 (3)	C3D—C4D—C5D	119.7 (3)
O2B—C5B—C6B	124.8 (3)	O2D—C5D—C6D	124.9 (3)
O2B—C5B—C4B	115.4 (2)	O2D—C5D—C4D	115.7 (2)
C6B—C5B—C4B	119.7 (3)	C6D—C5D—C4D	119.4 (3)
C5B—C6B—C1B	120.3 (3)	C5D—C6D—C1D	120.5 (3)
C5B—C6B—H6B	119.8	C5D—C6D—H6D	119.8
C1B—C6B—H6B	119.8	C1D—C6D—H6D	119.8
O1B—C7B—H7B1	109.5	O1D—C7D—H7D1	109.5
O1B—C7B—H7B2	109.5	O1D—C7D—H7D2	109.5
H7B1—C7B—H7B2	109.5	H7D1—C7D—H7D2	109.5
O1B—C7B—H7B3	109.5	O1D—C7D—H7D3	109.5
H7B1—C7B—H7B3	109.5	H7D1—C7D—H7D3	109.5
H7B2—C7B—H7B3	109.5	H7D2—C7D—H7D3	109.5
O2B—C8B—H8B1	109.5	O2D—C8D—H8D1	109.5
O2B—C8B—H8B2	109.5	O2D—C8D—H8D2	109.5
H8B1—C8B—H8B2	109.5	H8D1—C8D—H8D2	109.5
O2B—C8B—H8B3	109.5	O2D—C8D—H8D3	109.5
H8B1—C8B—H8B3	109.5	H8D1—C8D—H8D3	109.5
H8B2—C8B—H8B3	109.5	H8D2—C8D—H8D3	109.5
C6A—C1A—C2A—C3A	0.0 (4)	C6C—C1C—C2C—C3C	−0.3 (4)
Cl1E—C1A—C2A—C3A	−179.5 (12)	Cl1C—C1C—C2C—C3C	−177.9 (9)
Br1A—C1A—C2A—C3A	−179.2 (2)	Br1G—C1C—C2C—C3C	179.8 (4)
C6A—C1A—C2A—Cl1A	−179.4 (9)	C6C—C1C—C2C—Cl1G	−177.8 (8)
Cl1E—C1A—C2A—Cl1A	1.1 (15)	Cl1C—C1C—C2C—Cl1G	4.6 (12)
Br1A—C1A—C2A—Cl1A	1.4 (9)	Br1G—C1C—C2C—Cl1G	2.4 (9)
C6A—C1A—C2A—Br1E	−179.6 (10)	C6C—C1C—C2C—Br1C	178.6 (3)
Cl1E—C1A—C2A—Br1E	0.9 (16)	Cl1C—C1C—C2C—Br1C	1.0 (10)
Br1A—C1A—C2A—Br1E	1.2 (10)	Br1G—C1C—C2C—Br1C	−1.2 (5)
C1A—C2A—C3A—C4A	0.3 (4)	C1C—C2C—C3C—C4C	0.5 (4)
Cl1A—C2A—C3A—C4A	179.7 (9)	Cl1G—C2C—C3C—C4C	178.2 (7)
Br1E—C2A—C3A—C4A	180.0 (9)	Br1C—C2C—C3C—C4C	−178.5 (3)
C7A—O1A—C4A—C3A	−2.1 (4)	C7C—O1C—C4C—C3C	−0.5 (4)
C7A—O1A—C4A—C5A	178.3 (2)	C7C—O1C—C4C—C5C	179.0 (2)
C2A—C3A—C4A—O1A	179.9 (2)	C2C—C3C—C4C—O1C	179.2 (2)
C2A—C3A—C4A—C5A	−0.5 (4)	C2C—C3C—C4C—C5C	−0.3 (4)
C8A—O2A—C5A—C6A	−4.5 (4)	C8C—O2C—C5C—C6C	12.4 (4)
C8A—O2A—C5A—C4A	176.4 (2)	C8C—O2C—C5C—C4C	−167.7 (2)
O1A—C4A—C5A—O2A	−0.8 (4)	O1C—C4C—C5C—O2C	0.6 (4)
C3A—C4A—C5A—O2A	179.6 (2)	C3C—C4C—C5C—O2C	−179.8 (2)
O1A—C4A—C5A—C6A	−180.0 (2)	O1C—C4C—C5C—C6C	−179.5 (2)
C3A—C4A—C5A—C6A	0.4 (4)	C3C—C4C—C5C—C6C	0.1 (4)
O2A—C5A—C6A—C1A	−179.2 (2)	O2C—C5C—C6C—C1C	180.0 (2)
C4A—C5A—C6A—C1A	−0.1 (4)	C4C—C5C—C6C—C1C	0.1 (4)
C2A—C1A—C6A—C5A	−0.1 (4)	C2C—C1C—C6C—C5C	0.1 (4)
Cl1E—C1A—C6A—C5A	179.4 (11)	Cl1C—C1C—C6C—C5C	177.7 (9)
Br1A—C1A—C6A—C5A	179.1 (2)	Br1G—C1C—C6C—C5C	179.9 (4)
C6B—C1B—C2B—C3B	−0.2 (4)	C6D—C1D—C2D—C3D	0.9 (4)
Cl1B—C1B—C2B—C3B	177.6 (8)	Cl1D—C1D—C2D—C3D	179.0 (10)
Br1F—C1B—C2B—C3B	−178.3 (4)	Br1H—C1D—C2D—C3D	−178.2 (6)
C6B—C1B—C2B—Cl1F	177.8 (11)	C6D—C1D—C2D—Cl1H	−178.2 (10)
Cl1B—C1B—C2B—Cl1F	−4.4 (14)	Cl1D—C1D—C2D—Cl1H	−0.1 (14)
Br1F—C1B—C2B—Cl1F	−0.2 (12)	Br1H—C1D—C2D—Cl1H	2.7 (12)
C6B—C1B—C2B—Br1B	178.5 (4)	C6D—C1D—C2D—Br1D	179.3 (3)
Cl1B—C1B—C2B—Br1B	−3.7 (9)	Cl1D—C1D—C2D—Br1D	−2.6 (10)
Br1F—C1B—C2B—Br1B	0.4 (6)	Br1H—C1D—C2D—Br1D	0.2 (7)
C1B—C2B—C3B—C4B	−0.2 (4)	C1D—C2D—C3D—C4D	−0.6 (4)
Cl1F—C2B—C3B—C4B	−178.4 (10)	Cl1H—C2D—C3D—C4D	178.5 (10)
Br1B—C2B—C3B—C4B	−178.9 (4)	Br1D—C2D—C3D—C4D	−179.1 (3)
C7B—O1B—C4B—C3B	−0.6 (4)	C7D—O1D—C4D—C3D	−4.3 (4)
C7B—O1B—C4B—C5B	178.7 (2)	C7D—O1D—C4D—C5D	175.0 (2)
C2B—C3B—C4B—O1B	−179.6 (2)	C2D—C3D—C4D—O1D	179.2 (2)
C2B—C3B—C4B—C5B	1.2 (4)	C2D—C3D—C4D—C5D	−0.1 (4)
C8B—O2B—C5B—C6B	1.1 (4)	C8D—O2D—C5D—C6D	2.6 (4)
C8B—O2B—C5B—C4B	−178.6 (2)	C8D—O2D—C5D—C4D	−177.3 (2)
O1B—C4B—C5B—O2B	−1.3 (3)	O1D—C4D—C5D—O2D	1.1 (3)
C3B—C4B—C5B—O2B	178.0 (2)	C3D—C4D—C5D—O2D	−179.5 (2)
O1B—C4B—C5B—C6B	179.0 (2)	O1D—C4D—C5D—C6D	−178.8 (2)
C3B—C4B—C5B—C6B	−1.7 (4)	C3D—C4D—C5D—C6D	0.6 (4)
O2B—C5B—C6B—C1B	−178.4 (2)	O2D—C5D—C6D—C1D	179.7 (2)
C4B—C5B—C6B—C1B	1.2 (4)	C4D—C5D—C6D—C1D	−0.4 (4)
C2B—C1B—C6B—C5B	−0.3 (4)	C2D—C1D—C6D—C5D	−0.4 (4)
Cl1B—C1B—C6B—C5B	−178.2 (8)	Cl1D—C1D—C6D—C5D	−178.6 (9)
Br1F—C1B—C6B—C5B	177.8 (4)	Br1H—C1D—C6D—C5D	178.7 (6)