1,3,5-Tris(bromo-meth-yl)-2,4,6-trimeth-oxy-benzene.

There are three independent mol-ecules in the asymmetric unit of the title compound, C12H15Br3O3, two of which have approximate trigonal symmetry, the third being conformationally different as it adopts near mirror symmetry. The crystal structure features C-H⋯Br inter-actions, a weak C-H⋯O hydrogen bond, π-π inter-actions [minimum ring centroid separation = 3.4927 (18) Å] and a short Br⋯Br contact [3.5894 (5) Å], resulting in a three-dimensional supramolecular network.

Related literature

For the synthesis and sample applications of the title compound, see: Li et al. (2005 ▶); Kim et al. (2005 ▶); Holec et al. (2011 ▶); Simaan et al. (2003 ▶); Whiting & Hof (2012 ▶). For hydrogen bonds, see: Desiraju (2002 ▶); Steiner (2002 ▶). For halogen bonding, see: Awwadi et al. (2006 ▶); Metrangolo & Resnati (2008 ▶).

Experimental

Crystal data

C12H15Br3O3

M = 446.94

Triclinic,

a = 9.7508 (5) Å

b = 15.0974 (7) Å

c = 16.5500 (7) Å

α = 114.433 (2)°

β = 92.903 (2)°

γ = 97.510 (2)°

V = 2184.29 (18) Å3

Z = 6

Mo Kα radiation

μ = 8.31 mm−1

T = 100 K

0.55 × 0.44 × 0.27 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.092, T max = 0.213

44729 measured reflections

11474 independent reflections

9330 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.070

S = 1.02

11474 reflections

496 parameters

H-atom parameters constrained

Δρmax = 1.17 e Å−3

Δρmin = −1.10 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008441/zs2251sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008441/zs2251Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008441/zs2251Isup3.cml

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

C12H15Br3O3	Z = 6
Mr = 446.94	F(000) = 1296
Triclinic, P1	Dx = 2.039 Mg m−3
Hall symbol: -P 1	Melting point: 398 K
a = 9.7508 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.0974 (7) Å	Cell parameters from 9450 reflections
c = 16.5500 (7) Å	θ = 2.4–29.2°
α = 114.433 (2)°	µ = 8.31 mm−1
β = 92.903 (2)°	T = 100 K
γ = 97.510 (2)°	Block, colourless
V = 2184.29 (18) Å3	0.55 × 0.44 × 0.27 mm

Bruker APEXII CCD area-detector diffractometer	11474 independent reflections
Radiation source: fine-focus sealed tube	9330 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 28.9°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
Tmin = 0.092, Tmax = 0.213	k = −20→20
44729 measured reflections	l = −22→21

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0264P)2 + 3.7624P] where P = (Fo2 + 2Fc2)/3
11474 reflections	(Δ/σ)max < 0.001
496 parameters	Δρmax = 1.17 e Å−3
0 restraints	Δρmin = −1.10 e Å−3

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 > 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	1.00621 (3)	0.53065 (2)	0.15704 (2)	0.01897 (7)
Br2	0.37963 (3)	0.50849 (2)	0.298180 (19)	0.02310 (7)
Br3	0.62290 (4)	0.84512 (2)	0.16701 (2)	0.02290 (7)
O1	0.6269 (2)	0.39201 (14)	0.14146 (13)	0.0159 (4)
O2	0.3537 (2)	0.62713 (15)	0.12679 (13)	0.0175 (4)
O3	0.8075 (2)	0.62276 (15)	0.03078 (13)	0.0175 (4)
C1	0.7213 (3)	0.51009 (19)	0.08885 (16)	0.0117 (5)
C2	0.6141 (3)	0.47348 (19)	0.12529 (17)	0.0116 (5)
C3	0.4904 (3)	0.51168 (19)	0.13990 (17)	0.0114 (5)
C4	0.4777 (3)	0.5919 (2)	0.12020 (17)	0.0126 (5)
C5	0.5847 (3)	0.63304 (19)	0.08661 (17)	0.0119 (5)
C6	0.7045 (3)	0.5906 (2)	0.07095 (17)	0.0125 (5)
C7	0.8445 (3)	0.4616 (2)	0.06466 (18)	0.0149 (6)
H7A	0.8692	0.4604	0.0070	0.018*
H7B	0.8217	0.3925	0.0569	0.018*
C8	0.7034 (3)	0.4162 (2)	0.22684 (19)	0.0184 (6)
H8A	0.7886	0.4629	0.2354	0.028*
H8B	0.7278	0.3560	0.2285	0.028*
H8C	0.6457	0.4461	0.2745	0.028*
C9	0.3726 (3)	0.4622 (2)	0.16750 (18)	0.0158 (6)
H9A	0.3728	0.3902	0.1399	0.019*
H9B	0.2841	0.4738	0.1445	0.019*
C10	0.3348 (3)	0.6978 (2)	0.2145 (2)	0.0220 (6)
H10A	0.3246	0.6650	0.2545	0.033*
H10B	0.2510	0.7260	0.2108	0.033*
H10C	0.4160	0.7506	0.2378	0.033*
C11	0.5653 (3)	0.7161 (2)	0.06288 (18)	0.0170 (6)
H11A	0.4661	0.7091	0.0414	0.020*
H11B	0.6211	0.7133	0.0138	0.020*
C12	0.9015 (3)	0.7114 (2)	0.0875 (2)	0.0199 (6)
H12A	0.8698	0.7681	0.0826	0.030*
H12B	0.9951	0.7066	0.0690	0.030*
H12C	0.9035	0.7200	0.1496	0.030*
Br1A	0.49210 (3)	0.04165 (2)	0.135857 (19)	0.01964 (7)
Br2A	−0.15090 (4)	0.16662 (2)	0.10600 (3)	0.03205 (9)
Br3A	0.30371 (4)	0.42815 (2)	0.51703 (2)	0.02858 (8)
O1A	0.2461 (2)	0.19509 (14)	0.06502 (12)	0.0166 (4)
O2A	0.0067 (2)	0.31567 (15)	0.32249 (14)	0.0187 (4)
O3A	0.4567 (2)	0.22737 (15)	0.34440 (14)	0.0190 (4)
C1A	0.3562 (3)	0.21360 (19)	0.20460 (18)	0.0127 (5)
C2A	0.2423 (3)	0.22089 (19)	0.15496 (17)	0.0121 (5)
C3A	0.1271 (3)	0.25851 (19)	0.19418 (17)	0.0123 (5)
C4A	0.1243 (3)	0.28472 (19)	0.28527 (18)	0.0135 (5)
C5A	0.2333 (3)	0.27421 (19)	0.33681 (18)	0.0142 (6)
C6A	0.3492 (3)	0.24041 (19)	0.29556 (18)	0.0131 (5)
C7A	0.4828 (3)	0.1800 (2)	0.1627 (2)	0.0176 (6)
H7A1	0.5665	0.2222	0.2035	0.021*
H7A2	0.4844	0.1886	0.1066	0.021*
C8A	0.1973 (3)	0.0915 (2)	0.01111 (18)	0.0196 (6)
H8A1	0.2501	0.0526	0.0322	0.029*
H8A2	0.2105	0.0756	−0.0514	0.029*
H8A3	0.0982	0.0757	0.0159	0.029*
C9A	0.0112 (3)	0.2722 (2)	0.14060 (19)	0.0176 (6)
H9A1	0.0453	0.2743	0.0860	0.021*
H9A2	−0.0180	0.3363	0.1758	0.021*
C10A	0.0133 (4)	0.4206 (2)	0.3641 (2)	0.0234 (7)
H10D	0.0850	0.4497	0.4157	0.035*
H10E	−0.0772	0.4360	0.3840	0.035*
H10F	0.0364	0.4477	0.3210	0.035*
C11A	0.2225 (3)	0.2920 (2)	0.43150 (18)	0.0185 (6)
H11C	0.2709	0.2451	0.4449	0.022*
H11D	0.1232	0.2789	0.4395	0.022*
C12A	0.5650 (3)	0.3111 (2)	0.3896 (2)	0.0247 (7)
H12D	0.6494	0.2991	0.3598	0.037*
H12E	0.5845	0.3216	0.4518	0.037*
H12F	0.5348	0.3698	0.3879	0.037*
Br1B	−0.11391 (3)	0.31688 (2)	0.56329 (2)	0.02455 (7)
Br2B	0.06858 (4)	−0.00924 (3)	0.18891 (2)	0.03241 (9)
Br3B	0.51099 (3)	0.18450 (2)	0.54894 (2)	0.01948 (7)
O1B	−0.1658 (2)	0.05465 (17)	0.37834 (16)	0.0261 (5)
O2B	0.2856 (2)	−0.03484 (15)	0.37591 (14)	0.0199 (5)
O3B	0.1524 (2)	0.19733 (15)	0.64356 (12)	0.0183 (4)
C1B	−0.0038 (3)	0.1345 (2)	0.50967 (18)	0.0134 (5)
C2B	−0.0329 (3)	0.0707 (2)	0.41889 (19)	0.0147 (6)
C3B	0.0642 (3)	0.0156 (2)	0.37157 (18)	0.0144 (6)
C4B	0.1936 (3)	0.02553 (19)	0.41748 (17)	0.0114 (5)
C5B	0.2266 (3)	0.08767 (19)	0.50829 (17)	0.0109 (5)
C6B	0.1270 (3)	0.14209 (19)	0.55285 (17)	0.0113 (5)
C7B	−0.1125 (3)	0.1851 (2)	0.5607 (2)	0.0206 (6)
H7B1	−0.0971	0.1921	0.6228	0.025*
H7B2	−0.2048	0.1438	0.5338	0.025*
C8B	−0.1914 (4)	0.1133 (3)	0.3320 (2)	0.0293 (8)
H8B1	−0.1553	0.1828	0.3706	0.044*
H8B2	−0.2919	0.1051	0.3159	0.044*
H8B3	−0.1447	0.0922	0.2777	0.044*
C9B	0.0257 (4)	−0.0599 (2)	0.27820 (19)	0.0217 (7)
H9B1	−0.0753	−0.0855	0.2693	0.026*
H9B2	0.0761	−0.1156	0.2686	0.026*
C10B	0.3755 (3)	−0.0024 (2)	0.3238 (2)	0.0194 (6)
H10G	0.3190	0.0055	0.2773	0.029*
H10H	0.4353	−0.0515	0.2958	0.029*
H10I	0.4335	0.0609	0.3626	0.029*
C11B	0.3590 (3)	0.0895 (2)	0.55699 (19)	0.0152 (6)
H11E	0.3846	0.0227	0.5317	0.018*
H11F	0.3465	0.1077	0.6206	0.018*
C12B	0.2247 (3)	0.2960 (2)	0.67127 (19)	0.0209 (6)
H12G	0.3122	0.2942	0.6444	0.031*
H12H	0.2448	0.3279	0.7365	0.031*
H12I	0.1665	0.3334	0.6518	0.031*

	U11	U22	U33	U12	U13	U23
Br1	0.00939 (14)	0.02295 (15)	0.02450 (15)	0.00310 (11)	−0.00017 (11)	0.01013 (12)
Br2	0.02417 (17)	0.02506 (16)	0.01819 (14)	0.00046 (13)	0.00854 (12)	0.00773 (12)
Br3	0.03147 (19)	0.01265 (14)	0.02433 (15)	0.00570 (12)	0.01059 (13)	0.00620 (12)
O1	0.0178 (11)	0.0117 (9)	0.0171 (10)	0.0015 (8)	−0.0034 (8)	0.0060 (8)
O2	0.0115 (10)	0.0208 (10)	0.0169 (10)	0.0074 (8)	−0.0018 (8)	0.0036 (8)
O3	0.0198 (11)	0.0181 (10)	0.0131 (9)	−0.0012 (8)	0.0051 (8)	0.0062 (8)
C1	0.0125 (14)	0.0108 (12)	0.0069 (11)	0.0011 (10)	−0.0031 (10)	−0.0003 (10)
C2	0.0117 (14)	0.0109 (12)	0.0092 (12)	0.0011 (10)	−0.0023 (10)	0.0021 (10)
C3	0.0103 (13)	0.0113 (12)	0.0083 (11)	−0.0005 (10)	−0.0026 (10)	0.0010 (10)
C4	0.0102 (14)	0.0156 (13)	0.0080 (11)	0.0029 (11)	−0.0022 (10)	0.0012 (10)
C5	0.0141 (14)	0.0113 (12)	0.0075 (11)	0.0029 (10)	−0.0027 (10)	0.0013 (10)
C6	0.0132 (14)	0.0143 (13)	0.0066 (11)	0.0003 (11)	−0.0007 (10)	0.0020 (10)
C7	0.0120 (14)	0.0167 (14)	0.0123 (12)	0.0034 (11)	0.0005 (11)	0.0021 (11)
C8	0.0199 (16)	0.0198 (15)	0.0185 (14)	0.0040 (12)	−0.0001 (12)	0.0112 (12)
C9	0.0115 (14)	0.0187 (14)	0.0129 (12)	0.0001 (11)	−0.0013 (11)	0.0035 (11)
C10	0.0176 (16)	0.0213 (15)	0.0224 (15)	0.0057 (13)	0.0048 (13)	0.0038 (12)
C11	0.0217 (16)	0.0168 (14)	0.0146 (13)	0.0059 (12)	0.0006 (12)	0.0082 (11)
C12	0.0196 (16)	0.0169 (14)	0.0225 (15)	0.0004 (12)	0.0047 (13)	0.0083 (12)
Br1A	0.02175 (16)	0.01827 (14)	0.02136 (14)	0.00848 (12)	0.00611 (12)	0.00893 (12)
Br2A	0.01615 (17)	0.02113 (16)	0.0444 (2)	0.00290 (13)	−0.00690 (14)	0.00098 (14)
Br3A	0.0378 (2)	0.02262 (16)	0.01586 (14)	−0.00243 (14)	−0.00652 (13)	0.00207 (12)
O1A	0.0254 (12)	0.0141 (10)	0.0123 (9)	0.0040 (8)	0.0052 (8)	0.0070 (8)
O2A	0.0153 (11)	0.0169 (10)	0.0224 (10)	0.0039 (8)	0.0077 (9)	0.0061 (8)
O3A	0.0194 (11)	0.0167 (10)	0.0228 (10)	0.0000 (9)	−0.0052 (9)	0.0119 (9)
C1A	0.0129 (14)	0.0090 (12)	0.0182 (13)	0.0013 (10)	0.0031 (11)	0.0077 (10)
C2A	0.0164 (15)	0.0090 (12)	0.0112 (12)	−0.0005 (10)	0.0029 (11)	0.0052 (10)
C3A	0.0121 (14)	0.0096 (12)	0.0144 (12)	−0.0016 (10)	−0.0010 (11)	0.0055 (10)
C4A	0.0133 (14)	0.0097 (12)	0.0179 (13)	0.0013 (11)	0.0049 (11)	0.0060 (10)
C5A	0.0194 (15)	0.0090 (12)	0.0128 (12)	−0.0022 (11)	0.0018 (11)	0.0045 (10)
C6A	0.0149 (14)	0.0097 (12)	0.0162 (13)	−0.0014 (11)	−0.0005 (11)	0.0081 (11)
C7A	0.0157 (15)	0.0175 (14)	0.0231 (14)	0.0019 (12)	0.0052 (12)	0.0121 (12)
C8A	0.0232 (17)	0.0195 (15)	0.0120 (13)	0.0013 (13)	−0.0006 (12)	0.0038 (11)
C9A	0.0174 (15)	0.0156 (14)	0.0191 (14)	0.0020 (12)	−0.0011 (12)	0.0073 (11)
C10A	0.0230 (18)	0.0214 (16)	0.0205 (15)	0.0105 (13)	0.0019 (13)	0.0017 (12)
C11A	0.0242 (17)	0.0133 (13)	0.0161 (13)	−0.0016 (12)	0.0007 (12)	0.0058 (11)
C12A	0.0166 (16)	0.0233 (16)	0.0326 (17)	−0.0037 (13)	−0.0067 (13)	0.0135 (14)
Br1B	0.02098 (17)	0.01649 (14)	0.03671 (17)	0.00742 (12)	0.00790 (14)	0.01007 (13)
Br2B	0.0393 (2)	0.03877 (19)	0.01701 (15)	−0.01025 (16)	−0.00771 (14)	0.01582 (14)
Br3B	0.00936 (14)	0.02310 (15)	0.02693 (15)	−0.00075 (11)	−0.00188 (11)	0.01300 (12)
O1B	0.0120 (11)	0.0310 (12)	0.0411 (13)	−0.0071 (9)	−0.0111 (10)	0.0258 (11)
O2B	0.0269 (12)	0.0170 (10)	0.0243 (11)	0.0126 (9)	0.0171 (9)	0.0129 (9)
O3B	0.0257 (12)	0.0177 (10)	0.0100 (9)	0.0003 (9)	0.0035 (8)	0.0053 (8)
C1B	0.0100 (14)	0.0147 (13)	0.0210 (13)	0.0033 (11)	0.0060 (11)	0.0122 (11)
C2B	0.0080 (13)	0.0159 (13)	0.0226 (14)	−0.0051 (11)	−0.0049 (11)	0.0132 (12)
C3B	0.0177 (15)	0.0120 (13)	0.0138 (12)	−0.0024 (11)	−0.0015 (11)	0.0076 (11)
C4B	0.0138 (14)	0.0100 (12)	0.0138 (12)	0.0031 (10)	0.0057 (11)	0.0076 (10)
C5B	0.0090 (13)	0.0123 (12)	0.0141 (12)	0.0005 (10)	0.0029 (10)	0.0084 (10)
C6B	0.0134 (14)	0.0110 (12)	0.0102 (12)	0.0002 (10)	0.0028 (10)	0.0054 (10)
C7B	0.0159 (16)	0.0193 (15)	0.0349 (17)	0.0088 (12)	0.0109 (13)	0.0172 (13)
C8B	0.0264 (19)	0.0271 (17)	0.0370 (19)	0.0033 (14)	−0.0135 (15)	0.0185 (15)
C9B	0.0324 (19)	0.0172 (14)	0.0141 (13)	−0.0042 (13)	−0.0025 (13)	0.0082 (12)
C10B	0.0194 (16)	0.0219 (15)	0.0196 (14)	0.0071 (12)	0.0093 (12)	0.0098 (12)
C11B	0.0094 (14)	0.0196 (14)	0.0203 (14)	0.0007 (11)	0.0004 (11)	0.0128 (12)
C12B	0.0219 (17)	0.0184 (15)	0.0141 (13)	−0.0004 (12)	−0.0008 (12)	0.0002 (11)

Br1—C7	1.979 (3)	C3A—C9A	1.488 (4)
Br2—C9	1.973 (3)	C7A—H7A1	0.9900
Br3—C11	1.980 (3)	C7A—H7A2	0.9900
O1—C2	1.382 (3)	C8A—H8A1	0.9800
O1—C8	1.443 (3)	C8A—H8A2	0.9800
O2—C4	1.374 (3)	C8A—H8A3	0.9800
O2—C10	1.441 (3)	C9A—H9A1	0.9900
O3—C6	1.376 (3)	C9A—H9A2	0.9900
O3—C12	1.437 (4)	C10A—H10D	0.9800
C1—C6	1.393 (4)	C10A—H10E	0.9800
C1—C2	1.397 (4)	C10A—H10F	0.9800
C1—C7	1.475 (4)	C11A—H11C	0.9900
C2—C3	1.393 (4)	C11A—H11D	0.9900
C3—C4	1.397 (4)	C12A—H12D	0.9800
C3—C9	1.483 (4)	C12A—H12E	0.9800
C4—C5	1.399 (4)	C12A—H12F	0.9800
C5—C6	1.390 (4)	Br1B—C7B	1.974 (3)
C5—C11	1.491 (4)	Br2B—C9B	1.964 (3)
C7—H7A	0.9900	Br3B—C11B	1.973 (3)
C7—H7B	0.9900	O1B—C2B	1.373 (3)
C8—H8A	0.9800	O1B—C8B	1.425 (4)
C8—H8B	0.9800	O2B—C4B	1.366 (3)
C8—H8C	0.9800	O2B—C10B	1.437 (3)
C9—H9A	0.9900	O3B—C6B	1.372 (3)
C9—H9B	0.9900	O3B—C12B	1.433 (4)
C10—H10A	0.9800	C1B—C6B	1.397 (4)
C10—H10B	0.9800	C1B—C2B	1.398 (4)
C10—H10C	0.9800	C1B—C7B	1.480 (4)
C11—H11A	0.9900	C2B—C3B	1.394 (4)
C11—H11B	0.9900	C3B—C4B	1.397 (4)
C12—H12A	0.9800	C3B—C9B	1.483 (4)
C12—H12B	0.9800	C4B—C5B	1.396 (4)
C12—H12C	0.9800	C5B—C6B	1.394 (4)
Br1A—C7A	1.963 (3)	C5B—C11B	1.478 (4)
Br3A—C11A	1.977 (3)	C7B—H7B1	0.9900
Br2A—C9A	1.965 (3)	C7B—H7B2	0.9900
O3A—C6A	1.375 (3)	C8B—H8B1	0.9800
O3A—C12A	1.435 (4)	C8B—H8B2	0.9800
O2A—C4A	1.373 (3)	C8B—H8B3	0.9800
O2A—C10A	1.433 (4)	C9B—H9B1	0.9900
O1A—C2A	1.378 (3)	C9B—H9B2	0.9900
O1A—C8A	1.441 (3)	C10B—H10G	0.9800
C1A—C2A	1.391 (4)	C10B—H10H	0.9800
C1A—C6A	1.396 (4)	C10B—H10I	0.9800
C1A—C7A	1.490 (4)	C11B—H11E	0.9900
C6A—C5A	1.394 (4)	C11B—H11F	0.9900
C5A—C4A	1.395 (4)	C12B—H12G	0.9800
C5A—C11A	1.488 (4)	C12B—H12H	0.9800
C4A—C3A	1.394 (4)	C12B—H12I	0.9800
C3A—C2A	1.394 (4)
C2—O1—C8	113.5 (2)	H12D—C12A—H12E	109.5
C4—O2—C10	115.5 (2)	O3A—C12A—H12F	109.5
C6—O3—C12	116.2 (2)	H12D—C12A—H12F	109.5
C6—C1—C2	117.8 (3)	H12E—C12A—H12F	109.5
C6—C1—C7	120.7 (2)	C5A—C11A—Br3A	112.86 (18)
C2—C1—C7	121.4 (2)	C5A—C11A—H11C	109.0
O1—C2—C3	118.7 (2)	Br3A—C11A—H11C	109.0
O1—C2—C1	118.8 (2)	C5A—C11A—H11D	109.0
C3—C2—C1	122.3 (2)	Br3A—C11A—H11D	109.0
C2—C3—C4	117.8 (2)	H11C—C11A—H11D	107.8
C2—C3—C9	120.3 (2)	O2A—C10A—H10D	109.5
C4—C3—C9	121.6 (3)	O2A—C10A—H10E	109.5
O2—C4—C3	119.9 (2)	H10D—C10A—H10E	109.5
O2—C4—C5	118.3 (2)	O2A—C10A—H10F	109.5
C3—C4—C5	121.6 (3)	H10D—C10A—H10F	109.5
C6—C5—C4	118.4 (2)	H10E—C10A—H10F	109.5
C6—C5—C11	121.3 (2)	C3A—C9A—Br2A	112.80 (19)
C4—C5—C11	120.2 (3)	C3A—C9A—H9A1	109.0
O3—C6—C5	120.6 (2)	Br2A—C9A—H9A1	109.0
O3—C6—C1	117.2 (2)	C3A—C9A—H9A2	109.0
C5—C6—C1	122.0 (2)	Br2A—C9A—H9A2	109.0
C1—C7—Br1	111.74 (18)	H9A1—C9A—H9A2	107.8
C1—C7—H7A	109.3	O1A—C8A—H8A1	109.5
Br1—C7—H7A	109.3	O1A—C8A—H8A2	109.5
C1—C7—H7B	109.3	H8A1—C8A—H8A2	109.5
Br1—C7—H7B	109.3	O1A—C8A—H8A3	109.5
H7A—C7—H7B	107.9	H8A1—C8A—H8A3	109.5
O1—C8—H8A	109.5	H8A2—C8A—H8A3	109.5
O1—C8—H8B	109.5	C2B—O1B—C8B	116.6 (2)
H8A—C8—H8B	109.5	C4B—O2B—C10B	116.1 (2)
O1—C8—H8C	109.5	C6B—O3B—C12B	115.2 (2)
H8A—C8—H8C	109.5	C6B—C1B—C2B	118.0 (3)
H8B—C8—H8C	109.5	C6B—C1B—C7B	120.6 (3)
C3—C9—Br2	113.33 (19)	C2B—C1B—C7B	121.1 (3)
C3—C9—H9A	108.9	O1B—C2B—C3B	119.4 (3)
Br2—C9—H9A	108.9	O1B—C2B—C1B	118.3 (3)
C3—C9—H9B	108.9	C3B—C2B—C1B	121.9 (3)
Br2—C9—H9B	108.9	C2B—C3B—C4B	118.1 (2)
H9A—C9—H9B	107.7	C2B—C3B—C9B	120.9 (3)
O2—C10—H10A	109.5	C4B—C3B—C9B	120.6 (3)
O2—C10—H10B	109.5	O2B—C4B—C5B	118.0 (2)
H10A—C10—H10B	109.5	O2B—C4B—C3B	119.7 (2)
O2—C10—H10C	109.5	C5B—C4B—C3B	121.9 (3)
H10A—C10—H10C	109.5	C6B—C5B—C4B	118.1 (3)
H10B—C10—H10C	109.5	C6B—C5B—C11B	121.1 (2)
C5—C11—Br3	111.17 (18)	C4B—C5B—C11B	120.7 (2)
C5—C11—H11A	109.4	O3B—C6B—C5B	119.1 (2)
Br3—C11—H11A	109.4	O3B—C6B—C1B	118.6 (2)
C5—C11—H11B	109.4	C5B—C6B—C1B	122.0 (2)
Br3—C11—H11B	109.4	C1B—C7B—Br1B	113.00 (19)
H11A—C11—H11B	108.0	C1B—C7B—H7B1	109.0
O3—C12—H12A	109.5	Br1B—C7B—H7B1	109.0
O3—C12—H12B	109.5	C1B—C7B—H7B2	109.0
H12A—C12—H12B	109.5	Br1B—C7B—H7B2	109.0
O3—C12—H12C	109.5	H7B1—C7B—H7B2	107.8
H12A—C12—H12C	109.5	O1B—C8B—H8B1	109.5
H12B—C12—H12C	109.5	O1B—C8B—H8B2	109.5
C6A—O3A—C12A	116.2 (2)	H8B1—C8B—H8B2	109.5
C4A—O2A—C10A	114.8 (2)	O1B—C8B—H8B3	109.5
C2A—O1A—C8A	112.6 (2)	H8B1—C8B—H8B3	109.5
C2A—C1A—C6A	117.8 (3)	H8B2—C8B—H8B3	109.5
C2A—C1A—C7A	121.3 (2)	C3B—C9B—Br2B	113.29 (19)
C6A—C1A—C7A	120.9 (3)	C3B—C9B—H9B1	108.9
O3A—C6A—C5A	119.3 (2)	Br2B—C9B—H9B1	108.9
O3A—C6A—C1A	118.6 (3)	C3B—C9B—H9B2	108.9
C5A—C6A—C1A	122.0 (3)	Br2B—C9B—H9B2	108.9
C6A—C5A—C4A	118.1 (2)	H9B1—C9B—H9B2	107.7
C6A—C5A—C11A	120.7 (3)	O2B—C10B—H10G	109.5
C4A—C5A—C11A	121.0 (3)	O2B—C10B—H10H	109.5
O2A—C4A—C3A	118.1 (3)	H10G—C10B—H10H	109.5
O2A—C4A—C5A	120.2 (2)	O2B—C10B—H10I	109.5
C3A—C4A—C5A	121.6 (3)	H10G—C10B—H10I	109.5
C2A—C3A—C4A	118.3 (3)	H10H—C10B—H10I	109.5
C2A—C3A—C9A	120.9 (2)	C5B—C11B—Br3B	111.49 (18)
C4A—C3A—C9A	120.8 (3)	C5B—C11B—H11E	109.3
O1A—C2A—C1A	119.2 (2)	Br3B—C11B—H11E	109.3
O1A—C2A—C3A	118.6 (2)	C5B—C11B—H11F	109.3
C1A—C2A—C3A	122.1 (2)	Br3B—C11B—H11F	109.3
C1A—C7A—Br1A	113.43 (18)	H11E—C11B—H11F	108.0
C1A—C7A—H7A1	108.9	O3B—C12B—H12G	109.5
Br1A—C7A—H7A1	108.9	O3B—C12B—H12H	109.5
C1A—C7A—H7A2	108.9	H12G—C12B—H12H	109.5
Br1A—C7A—H7A2	108.9	O3B—C12B—H12I	109.5
H7A1—C7A—H7A2	107.7	H12G—C12B—H12I	109.5
O3A—C12A—H12D	109.5	H12H—C12B—H12I	109.5
O3A—C12A—H12E	109.5
C8—O1—C2—C3	−99.1 (3)	O2A—C4A—C3A—C9A	5.3 (4)
C8—O1—C2—C1	85.4 (3)	C5A—C4A—C3A—C9A	−178.7 (2)
C6—C1—C2—O1	178.4 (2)	C8A—O1A—C2A—C1A	87.6 (3)
C7—C1—C2—O1	2.1 (4)	C8A—O1A—C2A—C3A	−95.8 (3)
C6—C1—C2—C3	3.1 (4)	C6A—C1A—C2A—O1A	179.9 (2)
C7—C1—C2—C3	−173.1 (2)	C7A—C1A—C2A—O1A	0.9 (4)
O1—C2—C3—C4	−177.8 (2)	C6A—C1A—C2A—C3A	3.4 (4)
C1—C2—C3—C4	−2.6 (4)	C7A—C1A—C2A—C3A	−175.6 (2)
O1—C2—C3—C9	−3.3 (4)	C4A—C3A—C2A—O1A	−179.8 (2)
C1—C2—C3—C9	172.0 (2)	C9A—C3A—C2A—O1A	−1.0 (4)
C10—O2—C4—C3	85.7 (3)	C4A—C3A—C2A—C1A	−3.3 (4)
C10—O2—C4—C5	−99.5 (3)	C9A—C3A—C2A—C1A	175.6 (2)
C2—C3—C4—O2	174.9 (2)	C2A—C1A—C7A—Br1A	−101.2 (3)
C9—C3—C4—O2	0.4 (4)	C6A—C1A—C7A—Br1A	79.8 (3)
C2—C3—C4—C5	0.2 (4)	C6A—C5A—C11A—Br3A	90.0 (3)
C9—C3—C4—C5	−174.3 (2)	C4A—C5A—C11A—Br3A	−94.2 (3)
O2—C4—C5—C6	−173.3 (2)	C2A—C3A—C9A—Br2A	101.2 (3)
C3—C4—C5—C6	1.5 (4)	C4A—C3A—C9A—Br2A	−80.0 (3)
O2—C4—C5—C11	2.8 (4)	C8B—O1B—C2B—C3B	−90.8 (3)
C3—C4—C5—C11	177.6 (2)	C8B—O1B—C2B—C1B	95.9 (3)
C12—O3—C6—C5	80.3 (3)	C6B—C1B—C2B—O1B	173.1 (2)
C12—O3—C6—C1	−104.2 (3)	C7B—C1B—C2B—O1B	−1.0 (4)
C4—C5—C6—O3	174.3 (2)	C6B—C1B—C2B—C3B	−0.1 (4)
C11—C5—C6—O3	−1.7 (4)	C7B—C1B—C2B—C3B	−174.2 (2)
C4—C5—C6—C1	−0.9 (4)	O1B—C2B—C3B—C4B	−173.0 (2)
C11—C5—C6—C1	−176.9 (2)	C1B—C2B—C3B—C4B	0.1 (4)
C2—C1—C6—O3	−176.7 (2)	O1B—C2B—C3B—C9B	−0.1 (4)
C7—C1—C6—O3	−0.5 (4)	C1B—C2B—C3B—C9B	173.0 (2)
C2—C1—C6—C5	−1.3 (4)	C10B—O2B—C4B—C5B	−100.6 (3)
C7—C1—C6—C5	174.9 (2)	C10B—O2B—C4B—C3B	86.7 (3)
C6—C1—C7—Br1	83.6 (3)	C2B—C3B—C4B—O2B	173.0 (2)
C2—C1—C7—Br1	−100.3 (3)	C9B—C3B—C4B—O2B	0.1 (4)
C2—C3—C9—Br2	88.5 (3)	C2B—C3B—C4B—C5B	0.5 (4)
C4—C3—C9—Br2	−97.1 (3)	C9B—C3B—C4B—C5B	−172.4 (2)
C6—C5—C11—Br3	−95.2 (3)	O2B—C4B—C5B—C6B	−173.8 (2)
C4—C5—C11—Br3	88.8 (3)	C3B—C4B—C5B—C6B	−1.1 (4)
C12A—O3A—C6A—C5A	−89.9 (3)	O2B—C4B—C5B—C11B	1.5 (4)
C12A—O3A—C6A—C1A	93.9 (3)	C3B—C4B—C5B—C11B	174.1 (2)
C2A—C1A—C6A—O3A	175.7 (2)	C12B—O3B—C6B—C5B	88.6 (3)
C7A—C1A—C6A—O3A	−5.4 (4)	C12B—O3B—C6B—C1B	−97.7 (3)
C2A—C1A—C6A—C5A	−0.4 (4)	C4B—C5B—C6B—O3B	174.6 (2)
C7A—C1A—C6A—C5A	178.6 (2)	C11B—C5B—C6B—O3B	−0.6 (4)
O3A—C6A—C5A—C4A	−178.6 (2)	C4B—C5B—C6B—C1B	1.2 (4)
C1A—C6A—C5A—C4A	−2.5 (4)	C11B—C5B—C6B—C1B	−174.1 (2)
O3A—C6A—C5A—C11A	−2.6 (4)	C2B—C1B—C6B—O3B	−174.0 (2)
C1A—C6A—C5A—C11A	173.4 (2)	C7B—C1B—C6B—O3B	0.1 (4)
C10A—O2A—C4A—C3A	−95.9 (3)	C2B—C1B—C6B—C5B	−0.6 (4)
C10A—O2A—C4A—C5A	88.1 (3)	C7B—C1B—C6B—C5B	173.6 (2)
C6A—C5A—C4A—O2A	178.6 (2)	C6B—C1B—C7B—Br1B	93.5 (3)
C11A—C5A—C4A—O2A	2.6 (4)	C2B—C1B—C7B—Br1B	−92.5 (3)
C6A—C5A—C4A—C3A	2.7 (4)	C2B—C3B—C9B—Br2B	93.7 (3)
C11A—C5A—C4A—C3A	−173.3 (2)	C4B—C3B—C9B—Br2B	−93.5 (3)
O2A—C4A—C3A—C2A	−175.8 (2)	C6B—C5B—C11B—Br3B	−97.1 (3)
C5A—C4A—C3A—C2A	0.1 (4)	C4B—C5B—C11B—Br3B	87.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8A—H8A1···Br1A	0.98	2.91	3.787 (3)	150
C8—H8A···Br1	0.98	2.84	3.702 (3)	148
C8—H8C···Br2	0.98	2.86	3.670 (3)	140
C7B—H7B2···Br3Bi	0.99	2.92	3.665 (3)	133
C10—H10A···Br2	0.98	2.85	3.717 (3)	149
C10—H10C···Br3	0.98	2.89	3.673 (3)	138
C10A—H10D···Br3A	0.98	2.78	3.659 (4)	149
C10B—H10G···Br2B	0.98	2.72	3.606 (3)	151
C10B—H10I···Br3B	0.98	2.86	3.663 (3)	140
C11—H11B···O1Aii	0.99	2.55	3.429 (4)	148
C8B—H8B3···Br2B	0.98	2.85	3.697 (4)	146
C12B—H12G···Br3B	0.98	2.83	3.702 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8A—H8A1⋯Br1A	0.98	2.91	3.787 (3)	150
C8—H8A⋯Br1	0.98	2.84	3.702 (3)	148
C8—H8C⋯Br2	0.98	2.86	3.670 (3)	140
C7B—H7B2⋯Br3B i	0.99	2.92	3.665 (3)	133
C10—H10A⋯Br2	0.98	2.85	3.717 (3)	149
C10—H10C⋯Br3	0.98	2.89	3.673 (3)	138
C10A—H10D⋯Br3A	0.98	2.78	3.659 (4)	149
C10B—H10G⋯Br2B	0.98	2.72	3.606 (3)	151
C10B—H10I⋯Br3B	0.98	2.86	3.663 (3)	140
C11—H11B⋯O1A ii	0.99	2.55	3.429 (4)	148
C8B—H8B3⋯Br2B	0.98	2.85	3.697 (4)	146
C12B—H12G⋯Br3B	0.98	2.83	3.702 (3)	149

Symmetry codes: (i) ; (ii) .