(R)-3,3'-Dibromo-2,2'-dimeth­oxy-5,5',6,6',7,7',8,8'-octa­hydro-1,1'-binaphthalene: a Brönsted acid for catalyzing asymmetric Morita-Baylis-Hillman reactions

The title compound, C₂₂H₂₄Br₂O₂, consists of two substituted tetra­lin units that are connected through a C-C single bond; the aromatic rings are twisted by 80.2 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.010 Å
• Disorder in main residue
• R factor = 0.067
• wR factor = 0.187
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.00 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT301_ALERT_3_C Main Residue  Disorder .........................      13.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT731_ALERT_1_C Bond    Calc   1.382(11), Rep    1.383(5) ......       2.20 su-Ra
              C2   -C3      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc   1.383(11), Rep    1.383(5) ......       2.20 su-Ra
              C11  -C16     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc   1.386(11), Rep    1.386(5) ......       2.20 su-Ra
              C12  -C13     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc   1.381(12), Rep    1.381(5) ......       2.40 su-Ra
              C13  -C14     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc   1.387(11), Rep    1.387(5) ......       2.20 su-Ra
              C15  -C16     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc   1.490(12), Rep    1.490(5) ......       2.40 su-Ra
              C15  -C20     1.555   1.555
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.02

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.20
           From the CIF: _reflns_number_total               3842
           Count of symmetry unique reflns         2240
           Completeness (_total/calc)            171.52%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1602
           Fraction of Friedel pairs measured     0.715
           Are heavy atom types Z>Si present        yes
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

(R)-3,3'-Dibromo-2,2'-dimethoxy-5,5',6,6',7,7',8,8'-octahydro- 1,1'-binaphthalene

Crystal data

C22H24Br2O2	F(000) = 968
Mr = 480.23	Dx = 1.631 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2810 reflections
a = 9.778 (2) Å	θ = 2.1–22.1°
b = 11.787 (2) Å	µ = 4.16 mm^−1
c = 16.972 (3) Å	T = 295 K
V = 1956.1 (6) Å^3	Block, colourless
Z = 4	0.26 × 0.20 × 0.12 mm

Data collection

Bruker SMART 1K area-detector diffractometer	3842 independent reflections
Radiation source: fine-focus sealed tube	2505 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
φ and ω scans	θmax = 26.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→12
Tmin = 0.422, Tmax = 0.635	k = −11→14
10324 measured reflections	l = −21→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.187	w = 1/[σ^2(Fo^2) + (0.1069P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3842 reflections	Δρmax = 1.53 e Å^−3
247 parameters	Δρmin = −0.79 e Å^−3
44 restraints	Absolute structure: Flack (1983), 1368 Fridel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (2)

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.65396 (10)	0.34294 (9)	0.92585 (6)	0.0542 (3)
Br2	0.93206 (12)	−0.09272 (11)	0.58792 (6)	0.0652 (4)
O1	0.8123 (6)	0.1518 (6)	0.8544 (4)	0.0455 (16)
O2	0.7445 (6)	0.0599 (6)	0.6812 (4)	0.0491 (17)
C1	0.6275 (6)	0.0259 (6)	0.8284 (5)	0.034 (2)
C2	0.6763 (7)	0.1285 (6)	0.8567 (5)	0.032 (2)
C3	0.5870 (7)	0.2081 (7)	0.8872 (5)	0.041 (2)
C4	0.4480 (7)	0.1857 (6)	0.8876 (5)	0.046 (2)
H4	0.3872	0.2395	0.9072	0.055*
C5	0.3993 (6)	0.0832 (6)	0.8589 (5)	0.038 (2)
C6	0.4879 (5)	0.0027 (6)	0.8294 (5)	0.037 (2)
C7	0.4357 (7)	−0.1060 (6)	0.7963 (6)	0.052 (3)
H7A	0.4558	−0.1671	0.8327	0.062*	0.50
H7B	0.4826	−0.1220	0.7472	0.062*	0.50
H7C	0.4923	−0.1679	0.8150	0.062*	0.50
H7D	0.4427	−0.1037	0.7393	0.062*	0.50
C8	0.2850 (8)	−0.1021 (14)	0.7816 (9)	0.074 (7)	0.50
H8A	0.2517	−0.1779	0.7705	0.089*	0.50
H8B	0.2665	−0.0549	0.7360	0.089*	0.50
C9	0.2115 (11)	−0.0552 (8)	0.8517 (10)	0.062 (6)	0.50
H9A	0.2369	−0.0975	0.8985	0.075*	0.50
H9B	0.1136	−0.0627	0.8443	0.075*	0.50
C8'	0.2904 (9)	−0.1281 (8)	0.8189 (11)	0.074 (7)	0.50
H8'A	0.2861	−0.1501	0.8739	0.089*	0.50
H8'B	0.2546	−0.1901	0.7875	0.089*	0.50
C9'	0.2051 (10)	−0.0243 (11)	0.8060 (10)	0.062 (6)	0.50
H9'A	0.1094	−0.0424	0.8141	0.075*	0.50
H9'B	0.2162	0.0021	0.7522	0.075*	0.50
C10	0.2478 (6)	0.0672 (7)	0.8622 (6)	0.061 (3)
H10A	0.2049	0.1119	0.8211	0.073*	0.50
H10B	0.2136	0.0938	0.9126	0.073*	0.50
H10C	0.2025	0.1377	0.8485	0.073*	0.50
H10D	0.2208	0.0467	0.9153	0.073*	0.50
C11	0.7282 (8)	−0.0540 (6)	0.7962 (4)	0.035 (2)
C12	0.7765 (8)	−0.0370 (7)	0.7205 (4)	0.037 (2)
C13	0.8736 (8)	−0.1099 (7)	0.6892 (5)	0.049 (3)
C14	0.9188 (9)	−0.1999 (8)	0.7343 (4)	0.050 (3)
H14	0.9820	−0.2504	0.7130	0.060*
C15	0.8723 (8)	−0.2166 (7)	0.8103 (4)	0.049 (3)
C16	0.7714 (8)	−0.1460 (7)	0.8402 (4)	0.048 (2)
C17	0.7134 (9)	−0.1640 (8)	0.9207 (4)	0.060 (3)
H17A	0.6153	−0.1516	0.9195	0.072*	0.50
H17B	0.7532	−0.1098	0.9570	0.072*	0.50
H17C	0.6238	−0.1988	0.9163	0.072*	0.50
H17D	0.7024	−0.0913	0.9467	0.072*	0.50
C18	0.7424 (18)	−0.2823 (12)	0.9488 (10)	0.096 (12)	0.50
H18A	0.6913	−0.3365	0.9175	0.116*	0.50
H18B	0.7146	−0.2903	1.0034	0.116*	0.50
C19	0.8932 (19)	−0.3051 (18)	0.9411 (5)	0.092 (10)	0.50
H19A	0.9448	−0.2437	0.9648	0.110*	0.50
H19B	0.9165	−0.3749	0.9682	0.110*	0.50
C18'	0.804 (2)	−0.2384 (17)	0.9694 (5)	0.096 (12)	0.50
H18C	0.7577	−0.2588	1.0179	0.116*	0.50
H18D	0.8869	−0.1974	0.9831	0.116*	0.50
C19'	0.841 (2)	−0.3436 (12)	0.9248 (10)	0.092 (10)	0.50
H19C	0.7579	−0.3811	0.9070	0.110*	0.50
H19D	0.8895	−0.3955	0.9591	0.110*	0.50
C20	0.9281 (10)	−0.3148 (8)	0.8553 (5)	0.062 (3)
H20A	1.0267	−0.3175	0.8491	0.075*	0.50
H20B	0.8905	−0.3847	0.8343	0.075*	0.50
H20C	1.0198	−0.2969	0.8732	0.075*	0.50
H20D	0.9340	−0.3802	0.8207	0.075*	0.50
C21	0.8865 (9)	0.1211 (9)	0.9202 (6)	0.057 (3)
H21A	0.9809	0.1409	0.9126	0.086*
H21B	0.8789	0.0407	0.9282	0.086*
H21C	0.8514	0.1602	0.9655	0.086*
C22	0.6226 (11)	0.0525 (13)	0.6377 (7)	0.073 (4)
H22A	0.6057	0.1234	0.6117	0.109*
H22B	0.5480	0.0356	0.6725	0.109*
H22C	0.6308	−0.0067	0.5991	0.109*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0595 (6)	0.0390 (5)	0.0640 (7)	0.0000 (5)	−0.0017 (5)	−0.0128 (5)
Br2	0.0687 (7)	0.0663 (8)	0.0606 (7)	−0.0039 (6)	0.0239 (5)	−0.0167 (6)
O1	0.034 (3)	0.055 (4)	0.047 (4)	0.002 (3)	−0.001 (3)	−0.005 (4)
O2	0.049 (4)	0.045 (4)	0.053 (4)	−0.002 (3)	0.006 (3)	0.000 (3)
C1	0.030 (4)	0.025 (5)	0.046 (5)	0.012 (3)	0.004 (4)	0.001 (4)
C2	0.027 (4)	0.038 (6)	0.031 (4)	−0.003 (3)	0.007 (3)	0.000 (4)
C3	0.050 (6)	0.049 (6)	0.023 (4)	−0.003 (5)	0.002 (4)	−0.006 (4)
C4	0.037 (5)	0.045 (7)	0.054 (6)	0.019 (4)	0.003 (4)	−0.006 (4)
C5	0.032 (5)	0.032 (6)	0.050 (5)	0.001 (4)	−0.002 (4)	−0.007 (5)
C6	0.035 (5)	0.040 (6)	0.035 (5)	0.000 (4)	−0.002 (4)	−0.009 (4)
C7	0.050 (6)	0.037 (6)	0.068 (7)	0.000 (5)	0.008 (5)	−0.015 (5)
C8	0.059 (8)	0.114 (18)	0.049 (16)	−0.050 (10)	0.026 (9)	−0.022 (13)
C9	0.039 (7)	0.030 (10)	0.12 (2)	−0.002 (6)	−0.013 (10)	0.010 (10)
C8'	0.059 (8)	0.114 (18)	0.049 (16)	−0.050 (10)	0.026 (9)	−0.022 (13)
C9'	0.039 (7)	0.030 (10)	0.12 (2)	−0.002 (6)	−0.013 (10)	0.010 (10)
C10	0.047 (6)	0.079 (10)	0.056 (6)	0.013 (6)	0.001 (5)	−0.001 (6)
C11	0.037 (5)	0.029 (5)	0.040 (5)	0.012 (4)	−0.001 (4)	−0.011 (4)
C12	0.041 (5)	0.022 (5)	0.049 (6)	0.002 (4)	0.001 (4)	−0.004 (4)
C13	0.046 (6)	0.045 (7)	0.055 (6)	−0.004 (4)	−0.010 (4)	−0.014 (5)
C14	0.031 (5)	0.066 (8)	0.055 (6)	0.003 (5)	0.004 (4)	−0.025 (5)
C15	0.053 (6)	0.033 (6)	0.061 (7)	0.012 (4)	−0.009 (5)	−0.017 (5)
C16	0.040 (5)	0.054 (7)	0.050 (6)	0.010 (5)	−0.002 (4)	−0.013 (5)
C17	0.060 (6)	0.063 (7)	0.056 (7)	0.011 (5)	0.002 (5)	0.004 (6)
C18	0.16 (3)	0.074 (18)	0.053 (11)	0.08 (2)	0.014 (14)	0.008 (12)
C19	0.10 (2)	0.076 (18)	0.099 (15)	0.023 (16)	−0.006 (14)	0.032 (13)
C18'	0.16 (3)	0.074 (18)	0.053 (11)	0.08 (2)	0.014 (14)	0.008 (12)
C19'	0.10 (2)	0.076 (18)	0.099 (15)	0.023 (16)	−0.006 (14)	0.032 (13)
C20	0.072 (7)	0.048 (8)	0.067 (7)	0.028 (6)	−0.004 (6)	−0.005 (5)
C21	0.044 (5)	0.055 (8)	0.072 (7)	−0.004 (4)	−0.005 (5)	−0.003 (6)
C22	0.054 (7)	0.084 (11)	0.079 (8)	0.005 (6)	−0.008 (6)	0.014 (7)

Geometric parameters (Å, º)

Br1—C3	1.840 (8)	C11—C16	1.383 (5)
Br2—C13	1.822 (9)	C11—C12	1.385 (5)
O1—C2	1.358 (9)	C12—C13	1.386 (5)
O1—C21	1.380 (11)	C13—C14	1.381 (5)
O2—C12	1.358 (10)	C14—C15	1.383 (5)
O2—C22	1.406 (12)	C14—H14	0.93
C1—C2	1.386 (5)	C15—C16	1.387 (5)
C1—C6	1.392 (5)	C15—C20	1.490 (5)
C1—C11	1.467 (9)	C16—C17	1.494 (5)
C2—C3	1.383 (5)	C17—C18'	1.496 (5)
C3—C4	1.384 (5)	C17—C18	1.500 (5)
C4—C5	1.388 (5)	C17—H17A	0.97
C4—H4	0.93	C17—H17B	0.97
C5—C6	1.379 (5)	C17—H17C	0.97
C5—C10	1.494 (5)	C17—H17D	0.97
C6—C7	1.490 (5)	C18—C19	1.504 (5)
C7—C8'	1.494 (5)	C18—H18A	0.97
C7—C8	1.495 (5)	C18—H18B	0.97
C7—H7A	0.97	C19—C20	1.501 (5)
C7—H7B	0.97	C19—H19A	0.97
C7—H7C	0.97	C19—H19B	0.97
C7—H7D	0.97	C18'—C19'	1.497 (5)
C8—C9	1.495 (5)	C18'—H18C	0.97
C8—H8A	0.97	C18'—H18D	0.97
C8—H8B	0.97	C19'—C20	1.496 (5)
C9—C10	1.497 (5)	C19'—H19C	0.97
C9—H9A	0.97	C19'—H19D	0.97
C9—H9B	0.97	C20—H20A	0.97
C8'—C9'	1.497 (5)	C20—H20B	0.97
C8'—H8'A	0.97	C20—H20C	0.97
C8'—H8'B	0.97	C20—H20D	0.97
C9'—C10	1.499 (5)	C21—H21A	0.96
C9'—H9'A	0.97	C21—H21B	0.96
C9'—H9'B	0.97	C21—H21C	0.96
C10—H10A	0.97	C22—H22A	0.96
C10—H10B	0.97	C22—H22B	0.96
C10—H10C	0.97	C22—H22C	0.96
C10—H10D	0.97
C2—O1—C21	116.0 (7)	C11—C12—C13	120.0 (7)
C12—O2—C22	113.6 (8)	C14—C13—C12	118.9 (8)
C2—C1—C6	120.3 (6)	C14—C13—Br2	120.5 (5)
C2—C1—C11	117.2 (6)	C12—C13—Br2	120.5 (6)
C6—C1—C11	122.5 (6)	C13—C14—C15	121.4 (8)
O1—C2—C3	119.5 (6)	C13—C14—H14	119.3
O1—C2—C1	120.3 (6)	C15—C14—H14	119.3
C3—C2—C1	120.3 (7)	C14—C15—C16	119.4 (6)
C2—C3—C4	119.5 (7)	C14—C15—C20	117.9 (6)
C2—C3—Br1	119.6 (5)	C16—C15—C20	122.7 (5)
C4—C3—Br1	120.8 (5)	C11—C16—C15	119.4 (6)
C3—C4—C5	120.1 (7)	C11—C16—C17	119.3 (6)
C3—C4—H4	120.0	C15—C16—C17	121.3 (5)
C5—C4—H4	120.0	C16—C17—C18'	111.3 (6)
C6—C5—C4	120.7 (6)	C16—C17—C18	110.5 (6)
C6—C5—C10	123.4 (5)	C16—C17—H17A	109.5
C4—C5—C10	115.9 (6)	C18—C17—H17A	109.5
C5—C6—C1	119.1 (5)	C16—C17—H17B	109.5
C5—C6—C7	120.8 (5)	C18—C17—H17B	109.5
C1—C6—C7	120.0 (6)	H17A—C17—H17B	108.1
C6—C7—C8'	112.3 (5)	C16—C17—H17C	109.4
C6—C7—C8	112.0 (6)	C18'—C17—H17C	109.4
C6—C7—H7A	109.2	C16—C17—H17D	109.4
C8—C7—H7A	109.2	C18'—C17—H17D	109.4
C6—C7—H7B	109.2	H17C—C17—H17D	108.0
C8'—C7—H7B	129.5	C17—C18—C19	108.9 (7)
C8—C7—H7B	109.2	C17—C18—H18A	109.9
H7A—C7—H7B	107.9	C19—C18—H18A	109.9
C6—C7—H7C	109.1	C17—C18—H18B	109.9
C8'—C7—H7C	109.1	C19—C18—H18B	109.9
C8—C7—H7C	129.9	H18A—C18—H18B	108.3
C6—C7—H7D	109.1	C20—C19—C18	108.7 (7)
C8'—C7—H7D	109.1	C20—C19—H19A	109.9
H7C—C7—H7D	107.9	C18—C19—H19A	109.9
C7—C8—C9	110.6 (7)	C20—C19—H19B	109.9
C7—C8—H8A	109.5	C18—C19—H19B	109.9
C9—C8—H8A	109.5	H19A—C19—H19B	108.3
C7—C8—H8B	109.5	C17—C18'—C19'	110.3 (7)
C9—C8—H8B	109.5	C17—C18'—H18C	109.6
H8A—C8—H8B	108.1	C19'—C18'—H18C	109.6
C8—C9—C10	109.7 (7)	C17—C18'—H18D	109.6
C8—C9—H9A	109.7	C19'—C18'—H18D	109.6
C10—C9—H9A	109.7	H18C—C18'—H18D	108.1
C8—C9—H9B	109.7	C18'—C19'—C20	110.3 (7)
C10—C9—H9B	109.7	C18'—C19'—H19C	109.6
H9A—C9—H9B	108.2	C20—C19'—H19C	109.6
C7—C8'—C9'	110.5 (7)	C18'—C19'—H19D	109.6
C7—C8'—H8'A	109.6	C20—C19'—H19D	109.6
C9'—C8'—H8'A	109.6	H19C—C19'—H19D	108.1
C7—C8'—H8'B	109.6	C15—C20—C19'	111.7 (6)
C9'—C8'—H8'B	109.6	C15—C20—C19	110.7 (6)
H8'A—C8'—H8'B	108.1	C15—C20—H20A	109.5
C8'—C9'—C10	109.9 (7)	C19'—C20—H20A	130.2
C8'—C9'—H9'A	109.7	C19—C20—H20A	109.5
C10—C9'—H9'A	109.7	C15—C20—H20B	109.5
C8'—C9'—H9'B	109.7	C19—C20—H20B	109.5
C10—C9'—H9'B	109.7	H20A—C20—H20B	108.1
H9'A—C9'—H9'B	108.2	C15—C20—H20C	109.3
C5—C10—C9	110.6 (6)	C19'—C20—H20C	109.3
C5—C10—C9'	110.0 (6)	C15—C20—H20D	109.3
C5—C10—H10A	109.5	C19'—C20—H20D	109.3
C9—C10—H10A	109.5	H20C—C20—H20D	107.9
C5—C10—H10B	109.5	O1—C21—H21A	109.5
C9—C10—H10B	109.5	O1—C21—H21B	109.5
H10A—C10—H10B	108.1	H21A—C21—H21B	109.5
C5—C10—H10C	109.7	O1—C21—H21C	109.5
C9'—C10—H10C	109.7	H21A—C21—H21C	109.5
C5—C10—H10D	109.7	H21B—C21—H21C	109.5
C9'—C10—H10D	109.7	O2—C22—H22A	109.5
H10C—C10—H10D	108.2	O2—C22—H22B	109.5
C16—C11—C12	120.7 (6)	H22A—C22—H22B	109.5
C16—C11—C1	120.5 (6)	O2—C22—H22C	109.5
C12—C11—C1	118.8 (6)	H22A—C22—H22C	109.5
O2—C12—C11	119.9 (6)	H22B—C22—H22C	109.5
O2—C12—C13	119.4 (7)
C21—O1—C2—C3	89.4 (10)	C2—C1—C11—C12	−79.5 (10)
C21—O1—C2—C1	−90.9 (10)	C6—C1—C11—C12	99.1 (10)
C6—C1—C2—O1	−178.9 (8)	C22—O2—C12—C11	−89.3 (10)
C11—C1—C2—O1	−0.2 (12)	C22—O2—C12—C13	100.4 (10)
C6—C1—C2—C3	0.9 (13)	C16—C11—C12—O2	−173.0 (8)
C11—C1—C2—C3	179.5 (7)	C1—C11—C12—O2	8.5 (12)
O1—C2—C3—C4	178.2 (8)	C16—C11—C12—C13	−2.8 (13)
C1—C2—C3—C4	−1.5 (13)	C1—C11—C12—C13	178.8 (8)
O1—C2—C3—Br1	−1.1 (11)	O2—C12—C13—C14	171.3 (8)
C1—C2—C3—Br1	179.2 (6)	C11—C12—C13—C14	1.1 (13)
C2—C3—C4—C5	1.2 (14)	O2—C12—C13—Br2	−12.7 (12)
Br1—C3—C4—C5	−179.4 (7)	C11—C12—C13—Br2	177.0 (7)
C3—C4—C5—C6	−0.3 (14)	C12—C13—C14—C15	−1.9 (14)
C3—C4—C5—C10	179.8 (9)	Br2—C13—C14—C15	−177.8 (7)
C4—C5—C6—C1	−0.4 (14)	C13—C14—C15—C16	4.3 (14)
C10—C5—C6—C1	179.6 (9)	C13—C14—C15—C20	−179.0 (9)
C4—C5—C6—C7	−178.1 (9)	C12—C11—C16—C15	5.2 (14)
C10—C5—C6—C7	1.8 (15)	C1—C11—C16—C15	−176.4 (8)
C2—C1—C6—C5	0.1 (13)	C12—C11—C16—C17	−177.8 (8)
C11—C1—C6—C5	−178.5 (8)	C1—C11—C16—C17	0.6 (13)
C2—C1—C6—C7	177.9 (8)	C14—C15—C16—C11	−5.9 (14)
C11—C1—C6—C7	−0.7 (13)	C20—C15—C16—C11	177.6 (9)
C5—C6—C7—C8'	−15.5 (14)	C14—C15—C16—C17	177.2 (9)
C1—C6—C7—C8'	166.8 (11)	C20—C15—C16—C17	0.7 (15)
C5—C6—C7—C8	14.0 (13)	C11—C16—C17—C18'	−159.5 (13)
C1—C6—C7—C8	−163.7 (11)	C15—C16—C17—C18'	17.4 (16)
C6—C7—C8—C9	−47.6 (13)	C11—C16—C17—C18	164.4 (12)
C8'—C7—C8—C9	48.7 (9)	C15—C16—C17—C18	−18.7 (15)
C7—C8—C9—C10	67.1 (13)	C16—C17—C18—C19	52.5 (14)
C6—C7—C8'—C9'	47.1 (14)	C18'—C17—C18—C19	−45.4 (10)
C8—C7—C8'—C9'	−47.9 (10)	C17—C18—C19—C20	−70.6 (13)
C7—C8'—C9'—C10	−66.9 (13)	C16—C17—C18'—C19'	−50.0 (15)
C6—C5—C10—C9	16.1 (14)	C18—C17—C18'—C19'	45.4 (9)
C4—C5—C10—C9	−164.0 (10)	C17—C18'—C19'—C20	66.6 (14)
C6—C5—C10—C9'	−19.5 (14)	C14—C15—C20—C19'	−162.6 (13)
C4—C5—C10—C9'	160.4 (11)	C16—C15—C20—C19'	14.0 (17)
C8—C9—C10—C5	−49.0 (13)	C14—C15—C20—C19	166.8 (13)
C8—C9—C10—C9'	46.4 (8)	C16—C15—C20—C19	−16.7 (16)
C8'—C9'—C10—C5	50.6 (13)	C18'—C19'—C20—C15	−46.4 (15)
C8'—C9'—C10—C9	−46.7 (8)	C18'—C19'—C20—C19	47.3 (10)
C2—C1—C11—C16	102.0 (10)	C18—C19—C20—C15	50.2 (14)
C6—C1—C11—C16	−79.4 (12)	C18—C19—C20—C19'	−47.5 (10)