1,3,5-Tris(bromo­meth­yl)-2,4,6-tris­(2-methoxy­carbonyl-2-methyl­propyl)benzene

In the title compound, C₂₇H₃₉Br₃O₆, static gearing of the methyl­ene H atoms ensures that the β-groups alternate above (a) and below (b) the aromatic ring in a nearly trigonally symmetric conformation (ababab), resulting in the bromo substituents and ester groups being on opposite sides of the arene ring. A notable feature of the crystal packing is the inter­molecular inter­actions involving Br atoms: in each mol­ecule, two of the Br atoms are involved in inter­molecular Br...Br inter­actions [3.5911 (4) Å], while the third halogen makes two short contacts with the ester carbonyl O atom [Br...O 3.349 (2) Å] and one H atom of a CH₂ group of an ester functionality of another mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.026
• wR factor = 0.069
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.04 Ratio

Author Response: The hydrogen U for methyl groups is 1.5 times that of the C atom it is riding on. The methyl group that contains the largest Ueq is C13. We were unable to refine this group using a disorder model.

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.40 Ratio

Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT410_ALERT_2_C Short Intra H...H Contact  H22A   ..  H23A    ..       1.97 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H23B   ..  H30B    ..       1.95 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br2     ..       3.59 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br3    ..  O11     ..       3.35 Ang.

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

To the best of our knowledge, the first reported crystal structure of a hexasubstituted benzene was hexakisbromomethylbenzene (Marsau, 1965). Many other hexasubsituted benzenes have since been crystallized. The particularity of this class of compounds is their tendency to orient their 1,3,5 and 2,4,6 substituents respectively on the opposite side, above (a) and below (b), of the central ring due to static gearing (Iverson et al., 1981), resulting in an ababab pattern.

Hexasubstituted benzene analogues in which the functional groups are observed or predicted to point alternately up and down around the ring perimeter have been extensively studied mainly due to their applications in supramolecular chemistry. For example, this kind of system, which offers a preorganized site, has been used in the design of chlathrates (MacNicol et al., 1977), artificial receptors (Stack et al., 1993; Perreault et al., 1997; Wiskur et al., 2001) and self-assembling molecular capsules (Szabo et al., 1998).

While there are numerous crystal structures reported containing hexasubstituted benzene systems with the same six functional groups or with three functional groups in the 2,4, and 6-positions, the 1,3,5 positions bearing simple methyl or ethyl groups, very few (Hennrich et al., 2002) do not follow the ababab pattern. We report here the X-ray structure of a new molecular scaffold with alternating alkyl-bromo and alkyl-ester functions on either face of the six-membered ring.

The title compound, (C₆(CH₂Br)₃(CH₂C(CH₃)₂CO₂CH₃)₃) 1, is shown in Figure 1. As expected, the substituents adopt a three-up-three-down conformation (Figure 2). However, this result is contrary to the crystal structure of 1,3,5-tris(acetoxymethyl)-2,4,6-trithiophenyl benzene (Hennrich et al., 2002) for which the three-dimensional arrangement of substituents is 1,3-up, 5-down tris-(acetoxymethyl), 2,4-down, 6-up-trithiophenyl benzene.

Although usually unpredictable, crystal packing is often guided and assisted by weak interactions like hydrogen bonds (Desiraju, 2002; Steiner, 2002) or halogen bonds (Metrangolo et al., 2005). In our compound, both of these interactions are at work.

Thus, two bromine atoms per molecule (Figure 3) face two other bromine atomes of another molecule. Since the alignments are linear and the Br—Br distances are sufficiently short (Br1—Br2ⁱ/Br2—Br1ⁱ = 3.5911 (4) Å, i: -x, 1 - y, 1 - z), each pair of such neighboring bromine atoms is in fact brought together by a halogen bond (Awwadi et al., 2006). The remaining Br atom forms Br···H—C (Br3—H23aⁱⁱ = 2.904 Å, ii: -x, -y, 1 - z) and Br···O═C (Br3—O11ⁱⁱⁱ = 3.349 (2) Å, iii: -1 - x, -y, 2 - z) bonds (Auffinger et al., 2004) involving two different molecules.

Only one ester per molecule is part of such O—Br interactions.

In conclusion, the crystal structure of (C₆(CH₂Br)₃(CH₂C(CH₃)₂CO₂CH₃)₃) shows an original arrangement in which the crystal packing displays halogen bonds that do not disturb the intuitive alternate three-up-three-down conformation.

Related literature

For related literature, see: Auffinger et al. (2004); Awwadi et al., (2006); Desiraju (2002); Hennrich et al. (2002); Iverson et al. (1981); MacNicol et al. (1977); Marsau (1965); Metrangolo et al. (2005); Perreault et al. (1997); Stack et al. (1993); Steiner (2002); Szabo et al. (1998); Wiskur et al. (2001).

S2. Experimental

C₆(CH₃)₃(CH₂C (CH₃)₂CO₂CH₃)₃) was treated with NBS and Bz₂O₂ in CCl₄ under reflux to yield compound 1. A ether/pentane solution of C₆(CH₂Br)₃(CH₂ C(CH₃)₂CO₂CH₃)₃ was kept until complete evaporation of the solvent. Colourless, transparent crystals of 1 suitable for X-ray analysis were obtained.

S3. Refinement

Hydrogen atoms were placed in calculated positions and refined using a riding model.

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2000).

Figures

	Fig. 1. A molecular view of the title compound with thermal ellpsoids at the 50% level. Hydrogen atoms have been omitted for clarity.
	Fig. 2. Side view of 1 as a pipe and space filling model showing the ababab pattern of the substituents.
	Fig. 3. Main interactions involving the bromine atoms. Symmetry codes: i: -x, 1 - y, 1 - z; ii: -x, -y, 1 - z; iii: -1 - x, -y, 2 - z.

1,3,5-Tris(bromomethyl)-2,4,6-tris(2-methoxycarbonyl-2-methylpropyl)benzene

Crystal data

C27H39Br3O6	Z = 2
Mr = 699.31	F(000) = 708
Triclinic, P1	Dx = 1.600 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8160 (9) Å	Cell parameters from 5471 reflections
b = 10.9110 (9) Å	θ = 2.3–28.1°
c = 14.4422 (13) Å	µ = 4.21 mm^−1
α = 83.279 (2)°	T = 213 K
β = 70.934 (2)°	Parallelepiped, colourless
γ = 89.364 (2)°	0.40 × 0.38 × 0.28 mm
V = 1451.3 (2) Å^3

Data collection

Bruker SMART1000/P4 diffractometer	6311 independent reflections
Radiation source: fine-focus sealed tube, K760	5523 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
ϕ and ω scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −12→12
Tmin = 0.212, Tmax = 0.313	k = −14→13
10173 measured reflections	l = −17→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.069	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0379P)^2 + 0.5054P] where P = (Fo^2 + 2Fc^2)/3
6311 reflections	(Δ/σ)max = 0.001
334 parameters	Δρmax = 0.62 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

Experimental. Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.11458 (19)	0.17480 (16)	0.79133 (13)	0.0219 (4)
C2	−0.01962 (19)	0.27822 (16)	0.76904 (13)	0.0224 (4)
C3	0.11470 (19)	0.28177 (16)	0.69291 (13)	0.0219 (4)
C4	0.15113 (19)	0.18209 (16)	0.63661 (13)	0.0221 (4)
C5	0.05705 (19)	0.07814 (16)	0.65758 (13)	0.0213 (4)
C6	−0.07767 (19)	0.07690 (16)	0.73304 (13)	0.0214 (3)
C7	−0.2565 (2)	0.17176 (18)	0.87601 (13)	0.0260 (4)
H7A	−0.3279	0.1230	0.8607	0.031*
H7B	−0.2912	0.2561	0.8806	0.031*
C8	−0.2474 (2)	0.1163 (2)	0.97943 (15)	0.0347 (5)
C9	−0.2373 (3)	−0.0242 (2)	0.98707 (18)	0.0523 (7)
H9A	−0.2363	−0.0561	1.0524	0.078*
H9B	−0.1494	−0.0463	0.9380	0.078*
H9C	−0.3199	−0.0594	0.9756	0.078*
C10	−0.1218 (3)	0.1692 (3)	1.00545 (17)	0.0474 (6)
H10A	−0.1342	0.2569	1.0100	0.071*
H10B	−0.0315	0.1566	0.9545	0.071*
H10C	−0.1204	0.1276	1.0683	0.071*
C11	−0.3887 (3)	0.1479 (3)	1.05471 (16)	0.0428 (6)
O11	−0.4844 (2)	0.0769 (2)	1.09979 (17)	0.0838 (8)
O12	−0.3940 (2)	0.2676 (2)	1.06339 (17)	0.0709 (6)
C13	−0.5216 (4)	0.3084 (4)	1.1352 (3)	0.0938 (14)
H13A	−0.6067	0.2796	1.1231	0.141*
H13B	−0.5197	0.3979	1.1296	0.141*
H13C	−0.5241	0.2751	1.2010	0.141*
C14	−0.0685 (2)	0.39069 (18)	0.82093 (15)	0.0288 (4)
H14A	0.0154	0.4369	0.8228	0.035*
H14B	−0.1301	0.3655	0.8890	0.035*
C15	0.2184 (2)	0.39274 (16)	0.67068 (15)	0.0256 (4)
H15A	0.1611	0.4666	0.6844	0.031*
H15B	0.2728	0.4024	0.5999	0.031*
C16	0.3291 (2)	0.38894 (18)	0.72834 (15)	0.0293 (4)
C17	0.3977 (3)	0.2633 (2)	0.73542 (18)	0.0419 (5)
H17A	0.4618	0.2654	0.7740	0.063*
H17B	0.4520	0.2444	0.6697	0.063*
H17C	0.3227	0.2003	0.7670	0.063*
C18	0.4480 (3)	0.4877 (3)	0.6719 (2)	0.0494 (6)
H18A	0.5162	0.4920	0.7073	0.074*
H18B	0.4045	0.5674	0.6667	0.074*
H18C	0.4978	0.4658	0.6064	0.074*
C19	0.2559 (2)	0.42944 (18)	0.83050 (16)	0.0310 (4)
O19	0.2168 (2)	0.53239 (15)	0.84482 (14)	0.0494 (4)
O20	0.2371 (2)	0.33924 (15)	0.90415 (12)	0.0485 (4)
C21	0.1737 (4)	0.3742 (3)	1.0022 (2)	0.0643 (8)
H21A	0.2344	0.4371	1.0125	0.097*
H21B	0.1654	0.3025	1.0504	0.097*
H21C	0.0787	0.4064	1.0094	0.097*
C22	0.2857 (2)	0.19154 (18)	0.54706 (14)	0.0277 (4)
H22A	0.3190	0.1087	0.5325	0.033*
H22B	0.3625	0.2361	0.5600	0.033*
C23	0.1000 (2)	−0.03083 (16)	0.59799 (14)	0.0231 (4)
H23A	0.1613	0.0003	0.5310	0.028*
H23B	0.0127	−0.0679	0.5929	0.028*
C24	0.1823 (2)	−0.13454 (17)	0.64124 (15)	0.0263 (4)
C25	0.0828 (3)	−0.20735 (19)	0.73649 (15)	0.0358 (5)
H25A	0.0034	−0.2452	0.7230	0.054*
H25B	0.0452	−0.1518	0.7861	0.054*
H25C	0.1369	−0.2710	0.7605	0.054*
C26	0.3150 (3)	−0.0854 (2)	0.6614 (2)	0.0426 (6)
H26A	0.3591	−0.1530	0.6901	0.064*
H26B	0.2855	−0.0238	0.7069	0.064*
H26C	0.3842	−0.0483	0.5999	0.064*
C27	0.2345 (2)	−0.22309 (17)	0.56309 (14)	0.0275 (4)
O27	0.35750 (17)	−0.24632 (17)	0.52245 (13)	0.0462 (4)
O28	0.12400 (17)	−0.27239 (14)	0.54482 (12)	0.0417 (4)
C29	0.1565 (3)	−0.3534 (2)	0.46845 (19)	0.0461 (6)
H29A	0.2180	−0.3095	0.4068	0.069*
H29B	0.0676	−0.3800	0.4603	0.069*
H29C	0.2058	−0.4249	0.4870	0.069*
C30	−0.1906 (2)	−0.02155 (17)	0.74423 (14)	0.0259 (4)
H30A	−0.2463	−0.0428	0.8142	0.031*
H30B	−0.1440	−0.0962	0.7186	0.031*
Br1	−0.17711 (3)	0.49697 (2)	0.750578 (19)	0.04397 (7)
Br2	0.24186 (3)	0.28042 (2)	0.433048 (15)	0.03893 (7)
Br3	−0.31992 (2)	0.04030 (2)	0.670707 (16)	0.03421 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0200 (9)	0.0256 (9)	0.0186 (8)	0.0032 (7)	−0.0046 (7)	−0.0017 (7)
C2	0.0222 (9)	0.0220 (8)	0.0224 (9)	0.0030 (7)	−0.0062 (7)	−0.0042 (7)
C3	0.0202 (9)	0.0208 (8)	0.0243 (9)	0.0008 (7)	−0.0074 (7)	−0.0014 (7)
C4	0.0177 (8)	0.0245 (8)	0.0214 (9)	0.0016 (7)	−0.0035 (7)	−0.0014 (7)
C5	0.0210 (9)	0.0212 (8)	0.0214 (9)	0.0034 (7)	−0.0066 (7)	−0.0024 (7)
C6	0.0198 (8)	0.0215 (8)	0.0212 (9)	0.0006 (7)	−0.0050 (7)	−0.0004 (7)
C7	0.0198 (9)	0.0337 (10)	0.0215 (9)	0.0026 (7)	−0.0021 (7)	−0.0053 (7)
C8	0.0272 (10)	0.0501 (13)	0.0227 (10)	−0.0002 (9)	−0.0034 (8)	−0.0024 (9)
C9	0.0676 (18)	0.0522 (15)	0.0321 (12)	0.0066 (13)	−0.0144 (12)	0.0087 (11)
C10	0.0324 (12)	0.0808 (18)	0.0285 (12)	0.0001 (12)	−0.0111 (10)	−0.0008 (11)
C11	0.0317 (12)	0.0701 (16)	0.0226 (11)	−0.0052 (11)	−0.0018 (9)	−0.0104 (11)
O11	0.0522 (13)	0.1063 (18)	0.0619 (14)	−0.0280 (12)	0.0254 (11)	−0.0134 (13)
O12	0.0459 (11)	0.0826 (15)	0.0690 (14)	0.0033 (10)	0.0124 (10)	−0.0407 (12)
C13	0.0494 (19)	0.138 (4)	0.091 (3)	0.020 (2)	0.0015 (18)	−0.075 (3)
C14	0.0270 (10)	0.0292 (9)	0.0309 (10)	0.0050 (8)	−0.0084 (8)	−0.0099 (8)
C15	0.0250 (9)	0.0222 (9)	0.0298 (10)	−0.0014 (7)	−0.0094 (8)	−0.0020 (7)
C16	0.0244 (10)	0.0302 (10)	0.0346 (11)	0.0010 (8)	−0.0112 (8)	−0.0044 (8)
C17	0.0408 (13)	0.0473 (13)	0.0459 (13)	0.0209 (10)	−0.0223 (11)	−0.0171 (11)
C18	0.0322 (12)	0.0621 (16)	0.0539 (15)	−0.0173 (11)	−0.0151 (11)	−0.0018 (12)
C19	0.0296 (10)	0.0308 (10)	0.0389 (12)	0.0023 (8)	−0.0181 (9)	−0.0085 (8)
O19	0.0637 (12)	0.0342 (8)	0.0575 (11)	0.0153 (8)	−0.0264 (9)	−0.0167 (8)
O20	0.0722 (12)	0.0383 (9)	0.0334 (9)	0.0112 (8)	−0.0142 (8)	−0.0083 (7)
C21	0.088 (2)	0.0687 (19)	0.0360 (14)	0.0148 (16)	−0.0168 (15)	−0.0146 (13)
C22	0.0238 (9)	0.0285 (9)	0.0258 (10)	0.0005 (7)	−0.0017 (8)	−0.0028 (8)
C23	0.0241 (9)	0.0222 (8)	0.0224 (9)	0.0035 (7)	−0.0065 (7)	−0.0038 (7)
C24	0.0279 (10)	0.0230 (9)	0.0301 (10)	0.0056 (7)	−0.0110 (8)	−0.0070 (7)
C25	0.0486 (13)	0.0298 (10)	0.0280 (11)	0.0116 (9)	−0.0120 (10)	−0.0023 (8)
C26	0.0429 (13)	0.0336 (11)	0.0656 (16)	0.0105 (10)	−0.0352 (12)	−0.0133 (11)
C27	0.0290 (10)	0.0230 (9)	0.0284 (10)	0.0053 (7)	−0.0070 (8)	−0.0017 (7)
O27	0.0282 (8)	0.0646 (11)	0.0470 (10)	0.0181 (8)	−0.0093 (7)	−0.0223 (8)
O28	0.0315 (8)	0.0427 (9)	0.0515 (10)	−0.0007 (6)	−0.0065 (7)	−0.0289 (8)
C29	0.0538 (15)	0.0357 (12)	0.0518 (15)	0.0041 (10)	−0.0145 (12)	−0.0251 (11)
C30	0.0233 (9)	0.0239 (9)	0.0284 (10)	−0.0012 (7)	−0.0063 (8)	−0.0009 (7)
Br1	0.05016 (15)	0.03338 (12)	0.05592 (15)	0.01883 (10)	−0.02485 (12)	−0.01511 (10)
Br2	0.04493 (14)	0.03935 (12)	0.02538 (11)	−0.00344 (9)	−0.00353 (9)	0.00146 (8)
Br3	0.02797 (11)	0.04168 (12)	0.03524 (12)	0.00208 (8)	−0.01226 (9)	−0.00812 (9)

Geometric parameters (Å, º)

C1—C6	1.408 (2)	C16—C18	1.545 (3)
C1—C2	1.410 (3)	C17—H17A	0.9700
C1—C7	1.522 (2)	C17—H17B	0.9700
C2—C3	1.412 (3)	C17—H17C	0.9700
C2—C14	1.505 (2)	C18—H18A	0.9700
C3—C4	1.407 (2)	C18—H18B	0.9700
C3—C15	1.526 (2)	C18—H18C	0.9700
C4—C5	1.411 (2)	C19—O19	1.202 (2)
C4—C22	1.511 (2)	C19—O20	1.329 (3)
C5—C6	1.411 (2)	O20—C21	1.443 (3)
C5—C23	1.524 (2)	C21—H21A	0.9700
C6—C30	1.509 (2)	C21—H21B	0.9700
C7—C8	1.575 (3)	C21—H21C	0.9700
C7—H7A	0.9800	C22—Br2	1.979 (2)
C7—H7B	0.9800	C22—H22A	0.9800
C8—C11	1.522 (3)	C22—H22B	0.9800
C8—C9	1.529 (3)	C23—C24	1.571 (2)
C8—C10	1.538 (3)	C23—H23A	0.9800
C9—H9A	0.9700	C23—H23B	0.9800
C9—H9B	0.9700	C24—C27	1.529 (3)
C9—H9C	0.9700	C24—C25	1.537 (3)
C10—H10A	0.9700	C24—C26	1.539 (3)
C10—H10B	0.9700	C25—H25A	0.9700
C10—H10C	0.9700	C25—H25B	0.9700
C11—O11	1.186 (3)	C25—H25C	0.9700
C11—O12	1.326 (3)	C26—H26A	0.9700
O12—C13	1.446 (3)	C26—H26B	0.9700
C13—H13A	0.9700	C26—H26C	0.9700
C13—H13B	0.9700	C27—O27	1.196 (2)
C13—H13C	0.9700	C27—O28	1.330 (2)
C14—Br1	1.979 (2)	O28—C29	1.446 (2)
C14—H14A	0.9800	C29—H29A	0.9700
C14—H14B	0.9800	C29—H29B	0.9700
C15—C16	1.568 (3)	C29—H29C	0.9700
C15—H15A	0.9800	C30—Br3	1.9719 (19)
C15—H15B	0.9800	C30—H30A	0.9800
C16—C17	1.528 (3)	C30—H30B	0.9800
C16—C19	1.530 (3)
C6—C1—C2	119.19 (16)	C18—C16—C15	106.64 (17)
C6—C1—C7	121.01 (16)	C16—C17—H17A	109.5
C2—C1—C7	119.78 (16)	C16—C17—H17B	109.5
C1—C2—C3	120.94 (16)	H17A—C17—H17B	109.5
C1—C2—C14	119.17 (16)	C16—C17—H17C	109.5
C3—C2—C14	119.64 (16)	H17A—C17—H17C	109.5
C4—C3—C2	119.07 (16)	H17B—C17—H17C	109.5
C4—C3—C15	120.24 (16)	C16—C18—H18A	109.5
C2—C3—C15	120.68 (16)	C16—C18—H18B	109.5
C3—C4—C5	120.70 (16)	H18A—C18—H18B	109.5
C3—C4—C22	119.56 (16)	C16—C18—H18C	109.5
C5—C4—C22	119.50 (16)	H18A—C18—H18C	109.5
C4—C5—C6	119.43 (16)	H18B—C18—H18C	109.5
C4—C5—C23	120.09 (16)	O19—C19—O20	121.9 (2)
C6—C5—C23	120.47 (16)	O19—C19—C16	124.3 (2)
C1—C6—C5	120.50 (16)	O20—C19—C16	113.80 (17)
C1—C6—C30	118.93 (16)	C19—O20—C21	115.81 (19)
C5—C6—C30	120.17 (16)	O20—C21—H21A	109.5
C1—C7—C8	114.53 (16)	O20—C21—H21B	109.5
C1—C7—H7A	108.6	H21A—C21—H21B	109.5
C8—C7—H7A	108.6	O20—C21—H21C	109.5
C1—C7—H7B	108.6	H21A—C21—H21C	109.5
C8—C7—H7B	108.6	H21B—C21—H21C	109.5
H7A—C7—H7B	107.6	C4—C22—Br2	109.10 (13)
C11—C8—C9	108.2 (2)	C4—C22—H22A	109.9
C11—C8—C10	108.71 (19)	Br2—C22—H22A	109.9
C9—C8—C10	108.5 (2)	C4—C22—H22B	109.9
C11—C8—C7	105.47 (17)	Br2—C22—H22B	109.9
C9—C8—C7	111.31 (18)	H22A—C22—H22B	108.3
C10—C8—C7	114.43 (18)	C5—C23—C24	115.18 (15)
C8—C9—H9A	109.5	C5—C23—H23A	108.5
C8—C9—H9B	109.5	C24—C23—H23A	108.5
H9A—C9—H9B	109.5	C5—C23—H23B	108.5
C8—C9—H9C	109.5	C24—C23—H23B	108.5
H9A—C9—H9C	109.5	H23A—C23—H23B	107.5
H9B—C9—H9C	109.5	C27—C24—C25	108.36 (16)
C8—C10—H10A	109.5	C27—C24—C26	107.98 (17)
C8—C10—H10B	109.5	C25—C24—C26	108.85 (18)
H10A—C10—H10B	109.5	C27—C24—C23	106.26 (15)
C8—C10—H10C	109.5	C25—C24—C23	111.83 (16)
H10A—C10—H10C	109.5	C26—C24—C23	113.36 (16)
H10B—C10—H10C	109.5	C24—C25—H25A	109.5
O11—C11—O12	123.0 (2)	C24—C25—H25B	109.5
O11—C11—C8	125.7 (3)	H25A—C25—H25B	109.5
O12—C11—C8	111.3 (2)	C24—C25—H25C	109.5
C11—O12—C13	116.5 (3)	H25A—C25—H25C	109.5
O12—C13—H13A	109.5	H25B—C25—H25C	109.5
O12—C13—H13B	109.5	C24—C26—H26A	109.5
H13A—C13—H13B	109.5	C24—C26—H26B	109.5
O12—C13—H13C	109.5	H26A—C26—H26B	109.5
H13A—C13—H13C	109.5	C24—C26—H26C	109.5
H13B—C13—H13C	109.5	H26A—C26—H26C	109.5
C2—C14—Br1	109.75 (13)	H26B—C26—H26C	109.5
C2—C14—H14A	109.7	O27—C27—O28	123.31 (19)
Br1—C14—H14A	109.7	O27—C27—C24	125.74 (19)
C2—C14—H14B	109.7	O28—C27—C24	110.95 (16)
Br1—C14—H14B	109.7	C27—O28—C29	117.52 (17)
H14A—C14—H14B	108.2	O28—C29—H29A	109.5
C3—C15—C16	116.98 (15)	O28—C29—H29B	109.5
C3—C15—H15A	108.1	H29A—C29—H29B	109.5
C16—C15—H15A	108.1	O28—C29—H29C	109.5
C3—C15—H15B	108.1	H29A—C29—H29C	109.5
C16—C15—H15B	108.1	H29B—C29—H29C	109.5
H15A—C15—H15B	107.3	C6—C30—Br3	109.25 (12)
C17—C16—C19	111.47 (18)	C6—C30—H30A	109.8
C17—C16—C18	109.34 (19)	Br3—C30—H30A	109.8
C19—C16—C18	106.46 (18)	C6—C30—H30B	109.8
C17—C16—C15	113.15 (17)	Br3—C30—H30B	109.8
C19—C16—C15	109.45 (16)	H30A—C30—H30B	108.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23A···Br3^i	0.98	2.90	3.7875 (19)	151

Symmetry code: (i) −x, −y, −z+1.