(R)-3,3'-Bis(3,4,5-trifluoro­phen­yl)-1,1'-binaphthalene-2,2'-diol

The two fused-ring systems in the title mol­ecule, C₃₂H₁₆F₆O₂, are twisted by 73.5 (1)° about the central C-C single bond, thereby conferring chirality on the mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.070
• wR factor = 0.184
• Data-to-parameter ratio = 6.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ...         12
PLAT420_ALERT_2_B D-H Without Acceptor       O1     -   H1O    ...          ?
PLAT420_ALERT_2_B D-H Without Acceptor       O2     -   H2O    ...          ?

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.57
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C32 H16 F6 O2

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C32 H16 F6 O2
            Atom count from _chemical_formula_moiety:C32 H16 F2 O2
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           25.00
           From the CIF: _reflns_number_total               2378
           Count of symmetry unique reflns         2386
           Completeness (_total/calc)             99.66%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

We have reported two chiral, substituted BINOL [(1,1'-binaphthalene-2,2'-diol] derivatives recently (He & Ng, 2006, 2007). Our studies continue with the crystal structure determinarion of title compound. A tin(IV) derivative is a chiral tin alkoxide this is an efficient Lewis-acidic catalyst for enantionselective Diels-Alder reactions (Kano et al., 2006). In the title molecule the two fused-rings are twisted along the central carbon–carbon single bond that confers chirality to the molecule by 73.5 (1) °. The two hydroxy groups do not engage in any hydrogen bonding interactions.

Related literature

For the synthesis of the compound, see: Kano et al. (2006).

For related literature, see: He & Ng (2006, 2007).

S2. Experimental

The chiral compound was synthesized by the procedure of Kano et al. (2006), and crystals were grown from its solution in ethanol. However, the starting BINOL [(1,1'-binaphthalene-2,2'-diol] had an R- instead of an S-configuration. Methylation of (R)-1,1'-binaphthalene-2,2'-diol with methyl iodide gave dimethoxybinaphthyl; this was treated with n-butyl lithium and N,N,N',N'-tetramethylenediamine in ether at room temperature to give the dilithiated compound, which was brominated at 195 K to afford the dibromide. The dibromide was coupled with 3,4,5-trifluorophenylmagnesium bromide in the presence of commercially available dichlorobis(triphenylphosphinenickel as a catalyst; the product was demethylated to give the title compound.

S3. Refinement

In the absence of significant anomalous dispersion effects Friedel pairs were merged. The R-configuration was selected on the basis of the starting material. The oxygen- and carbon-bound H-atoms were generated geometrically (O—H 0.82 Å and C—H 0.93 Å), and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U_eq(C,O).

The configuration selected is the R-enantiomer.

Computing details

Data collection: DIFRAC (Gabe et al., 1993); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); 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: publCIF (Westrip, 2007).

Figures

Fig. 1. The molecular structure with displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius.

(R)-3,3'-Bis(3,4,5-trifluorophenyl)-1,1'-binaphthalene-2,2'-diol

Crystal data

C32H16F2O2	F(000) = 556
Mr = 546.45	Dx = 1.451 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 24 reflections
a = 12.440 (4) Å	θ = 4.9–7.5°
b = 7.466 (3) Å	µ = 0.12 mm^−1
c = 14.443 (5) Å	T = 295 K
β = 111.22 (3)°	Block, colourless
V = 1250.5 (8) Å^3	0.25 × 0.25 × 0.18 mm
Z = 2

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.006
Radiation source: medium-focus sealed tube	θmax = 25.0°, θmin = 1.5°
Graphite monochromator	h = −14→13
ω/2θ scans	k = −1→8
2385 measured reflections	l = −4→17
2378 independent reflections	3 standard reflections every 60 min
1302 reflections with I > 2σ(I)	intensity decay: 3.6%

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.184	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
2378 reflections	(Δ/σ)max = 0.001
362 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

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

	x	y	z	Uiso*/Ueq
F1	0.2343 (5)	0.5000 (12)	0.5656 (5)	0.123 (3)
F2	0.1556 (5)	0.8419 (9)	0.5493 (5)	0.115 (2)
F3	−0.0080 (6)	0.9311 (7)	0.6199 (4)	0.0989 (19)
F4	−0.6890 (5)	0.2983 (9)	0.9932 (4)	0.097 (2)
F5	−0.6902 (5)	0.6582 (9)	0.9799 (4)	0.101 (2)
F6	−0.5947 (8)	0.8181 (8)	0.8609 (6)	0.131 (3)
O1	−0.2115 (4)	0.4216 (7)	0.6543 (4)	0.0578 (15)
H1O	−0.2775	0.3822	0.6356	0.069*
O2	−0.3059 (4)	0.4018 (7)	0.8444 (4)	0.0584 (15)
H2O	−0.2366	0.3935	0.8555	0.070*
C1	0.1105 (6)	0.4153 (12)	0.6469 (6)	0.064 (2)
H1	0.1385	0.2988	0.6516	0.077*
C2	0.1510 (7)	0.5459 (16)	0.6029 (7)	0.074 (3)
C3	0.1132 (8)	0.7189 (15)	0.5942 (7)	0.075 (3)
C4	0.0327 (8)	0.7594 (13)	0.6315 (6)	0.068 (2)
C5	−0.0149 (8)	0.6364 (11)	0.6768 (6)	0.060 (2)
H5	−0.0718	0.6696	0.7011	0.072*
C6	0.0253 (6)	0.4612 (11)	0.6849 (5)	0.0474 (19)
C7	−0.0189 (6)	0.3195 (10)	0.7359 (5)	0.0442 (18)
C8	0.0531 (6)	0.1995 (11)	0.7967 (6)	0.052 (2)
H8	0.1318	0.2124	0.8104	0.062*
C9	0.0159 (6)	0.0541 (11)	0.8412 (5)	0.0443 (17)
C10	0.0923 (7)	−0.0752 (13)	0.9012 (6)	0.063 (2)
H10	0.1708	−0.0670	0.9130	0.075*
C11	0.0526 (7)	−0.2098 (13)	0.9413 (5)	0.065 (2)
H11	0.1041	−0.2950	0.9797	0.078*
C12	−0.0626 (7)	−0.2249 (12)	0.9269 (6)	0.061 (2)
H12	−0.0876	−0.3196	0.9559	0.073*
C13	−0.1411 (7)	−0.1022 (11)	0.8704 (5)	0.054 (2)
H13	−0.2186	−0.1116	0.8621	0.065*
C14	−0.1022 (6)	0.0399 (10)	0.8245 (5)	0.0428 (17)
C15	−0.1812 (6)	0.1692 (9)	0.7612 (5)	0.0404 (17)
C16	−0.1382 (6)	0.3031 (10)	0.7189 (5)	0.0422 (17)
C17	−0.5886 (6)	0.2731 (10)	0.8830 (5)	0.052 (2)
H17	−0.5905	0.1489	0.8867	0.062*
C18	−0.6390 (7)	0.3785 (12)	0.9343 (6)	0.066 (3)
C19	−0.6397 (7)	0.5568 (14)	0.9287 (6)	0.066 (2)
C20	−0.5907 (9)	0.6369 (11)	0.8695 (7)	0.068 (3)
C21	−0.5354 (8)	0.5422 (12)	0.8169 (6)	0.065 (2)
H21	−0.5005	0.5998	0.7780	0.079*
C22	−0.5347 (6)	0.3574 (10)	0.8254 (6)	0.0463 (19)
C23	−0.4783 (6)	0.2434 (9)	0.7710 (5)	0.0404 (17)
C24	−0.5403 (6)	0.1043 (9)	0.7110 (5)	0.0428 (18)
H24	−0.6176	0.0883	0.7018	0.051*
C25	−0.4869 (6)	−0.0125 (10)	0.6639 (5)	0.0473 (19)
C26	−0.5508 (7)	−0.1538 (11)	0.6018 (6)	0.060 (2)
H26	−0.6281	−0.1712	0.5923	0.071*
C27	−0.4964 (8)	−0.2639 (11)	0.5564 (6)	0.062 (2)
H27	−0.5373	−0.3586	0.5178	0.075*
C28	−0.3845 (7)	−0.2387 (11)	0.5660 (6)	0.058 (2)
H28	−0.3514	−0.3121	0.5317	0.069*
C29	−0.3209 (7)	−0.1062 (10)	0.6260 (5)	0.0481 (19)
H29	−0.2438	−0.0914	0.6338	0.058*
C30	−0.3717 (6)	0.0087 (9)	0.6763 (5)	0.0382 (16)
C31	−0.3087 (6)	0.1503 (10)	0.7384 (5)	0.0427 (18)
C32	−0.3635 (6)	0.2634 (9)	0.7828 (5)	0.0421 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.096 (4)	0.168 (7)	0.148 (5)	0.013 (5)	0.098 (4)	0.025 (5)
F2	0.117 (4)	0.122 (6)	0.127 (5)	−0.037 (4)	0.071 (4)	0.041 (4)
F3	0.159 (5)	0.050 (3)	0.108 (4)	−0.018 (4)	0.072 (4)	0.010 (3)
F4	0.120 (4)	0.095 (4)	0.123 (4)	−0.013 (4)	0.102 (4)	−0.013 (4)
F5	0.115 (5)	0.092 (4)	0.124 (5)	0.037 (4)	0.076 (4)	−0.027 (4)
F6	0.228 (8)	0.039 (3)	0.168 (6)	0.037 (4)	0.121 (6)	0.002 (4)
O1	0.050 (3)	0.052 (3)	0.083 (4)	0.009 (3)	0.037 (3)	0.029 (3)
O2	0.055 (3)	0.052 (3)	0.080 (3)	−0.007 (3)	0.040 (3)	−0.022 (3)
C1	0.062 (5)	0.069 (6)	0.081 (6)	−0.002 (5)	0.049 (5)	0.005 (5)
C2	0.061 (5)	0.097 (8)	0.088 (6)	0.000 (6)	0.057 (5)	0.001 (6)
C3	0.077 (6)	0.083 (7)	0.076 (6)	−0.030 (6)	0.042 (5)	0.012 (6)
C4	0.085 (6)	0.058 (6)	0.069 (6)	−0.013 (5)	0.039 (5)	0.000 (5)
C5	0.082 (6)	0.044 (5)	0.065 (5)	−0.009 (5)	0.041 (5)	−0.001 (4)
C6	0.050 (4)	0.052 (5)	0.052 (4)	−0.006 (4)	0.032 (4)	−0.007 (4)
C7	0.046 (4)	0.035 (4)	0.062 (5)	−0.002 (4)	0.032 (4)	0.003 (4)
C8	0.047 (4)	0.056 (5)	0.065 (5)	−0.003 (4)	0.034 (4)	−0.002 (4)
C9	0.051 (4)	0.043 (4)	0.041 (4)	−0.002 (4)	0.019 (4)	−0.007 (4)
C10	0.064 (5)	0.062 (6)	0.067 (5)	0.019 (5)	0.031 (5)	0.002 (5)
C11	0.083 (6)	0.059 (5)	0.049 (5)	0.016 (5)	0.020 (5)	0.011 (5)
C12	0.078 (6)	0.046 (5)	0.063 (5)	0.012 (5)	0.031 (5)	0.018 (4)
C13	0.068 (5)	0.051 (5)	0.057 (5)	0.006 (4)	0.039 (4)	0.010 (4)
C14	0.046 (4)	0.043 (4)	0.044 (4)	0.010 (4)	0.023 (3)	0.005 (4)
C15	0.055 (4)	0.033 (4)	0.046 (4)	0.001 (3)	0.033 (4)	−0.001 (3)
C16	0.048 (4)	0.036 (4)	0.050 (4)	0.005 (4)	0.028 (4)	0.001 (4)
C17	0.064 (5)	0.040 (4)	0.070 (5)	0.006 (4)	0.048 (4)	−0.005 (4)
C18	0.078 (6)	0.063 (7)	0.088 (7)	−0.007 (5)	0.067 (6)	−0.012 (5)
C19	0.068 (6)	0.066 (6)	0.075 (6)	0.030 (5)	0.037 (5)	−0.012 (5)
C20	0.087 (7)	0.036 (5)	0.087 (6)	0.023 (5)	0.038 (6)	−0.001 (5)
C21	0.090 (6)	0.046 (5)	0.085 (6)	0.011 (5)	0.060 (5)	0.004 (5)
C22	0.053 (4)	0.038 (4)	0.064 (5)	0.004 (3)	0.040 (4)	−0.005 (4)
C23	0.050 (4)	0.033 (4)	0.047 (4)	0.004 (4)	0.027 (4)	0.000 (4)
C24	0.044 (4)	0.041 (4)	0.055 (4)	0.002 (4)	0.032 (4)	0.002 (4)
C25	0.061 (5)	0.039 (4)	0.051 (4)	0.001 (4)	0.031 (4)	0.002 (4)
C26	0.072 (5)	0.052 (5)	0.062 (5)	−0.013 (4)	0.033 (4)	−0.002 (4)
C27	0.099 (6)	0.032 (4)	0.062 (5)	−0.006 (4)	0.036 (5)	−0.010 (4)
C28	0.083 (6)	0.046 (5)	0.052 (4)	0.004 (5)	0.034 (4)	−0.009 (4)
C29	0.060 (4)	0.049 (5)	0.042 (4)	0.014 (4)	0.027 (4)	0.005 (4)
C30	0.052 (4)	0.031 (4)	0.040 (4)	−0.001 (3)	0.026 (3)	0.001 (3)
C31	0.050 (4)	0.042 (4)	0.045 (4)	0.007 (4)	0.029 (4)	0.003 (4)
C32	0.058 (4)	0.033 (4)	0.044 (4)	−0.001 (4)	0.029 (4)	−0.002 (3)

Geometric parameters (Å, º)

F1—C2	1.374 (9)	C13—C14	1.426 (10)
F2—C3	1.337 (10)	C13—H13	0.9300
F3—C4	1.367 (11)	C14—C15	1.442 (10)
F4—C18	1.361 (9)	C15—C16	1.377 (9)
F5—C19	1.361 (9)	C15—C31	1.506 (9)
F6—C20	1.357 (10)	C17—C18	1.378 (10)
O1—C16	1.367 (9)	C17—C22	1.392 (9)
O1—H1O	0.8200	C17—H17	0.9300
O2—C32	1.382 (8)	C18—C19	1.333 (13)
O2—H2O	0.8200	C19—C20	1.355 (12)
C1—C2	1.356 (12)	C20—C21	1.389 (11)
C1—C6	1.402 (9)	C21—C22	1.385 (12)
C1—H1	0.9300	C21—H21	0.9300
C2—C3	1.365 (15)	C22—C23	1.494 (9)
C3—C4	1.332 (12)	C23—C32	1.384 (9)
C4—C5	1.379 (11)	C23—C24	1.393 (9)
C5—C6	1.390 (11)	C24—C25	1.410 (9)
C5—H5	0.9300	C24—H24	0.9300
C6—C7	1.503 (10)	C25—C30	1.388 (9)
C7—C8	1.344 (10)	C25—C26	1.425 (11)
C7—C16	1.420 (9)	C26—C27	1.373 (11)
C8—C9	1.422 (11)	C26—H26	0.9300
C8—H8	0.9300	C27—C28	1.361 (10)
C9—C14	1.405 (9)	C27—H27	0.9300
C9—C10	1.410 (11)	C28—C29	1.364 (10)
C10—C11	1.340 (12)	C28—H28	0.9300
C10—H10	0.9300	C29—C30	1.413 (9)
C11—C12	1.377 (10)	C29—H29	0.9300
C11—H11	0.9300	C30—C31	1.424 (9)
C12—C13	1.372 (10)	C31—C32	1.380 (9)
C12—H12	0.9300
C16—O1—H1O	109.5	C15—C16—C7	122.4 (7)
C32—O2—H2O	109.5	C18—C17—C22	118.3 (7)
C2—C1—C6	118.0 (8)	C18—C17—H17	120.8
C2—C1—H1	121.0	C22—C17—H17	120.8
C6—C1—H1	121.0	C19—C18—F4	118.9 (8)
C1—C2—C3	123.4 (7)	C19—C18—C17	122.1 (8)
C1—C2—F1	117.7 (10)	F4—C18—C17	119.0 (8)
C3—C2—F1	118.9 (9)	C18—C19—C20	119.0 (7)
C4—C3—F2	121.8 (10)	C18—C19—F5	121.1 (9)
C4—C3—C2	117.5 (8)	C20—C19—F5	119.9 (9)
F2—C3—C2	120.8 (9)	C19—C20—F6	119.2 (8)
C3—C4—F3	117.6 (8)	C19—C20—C21	123.0 (7)
C3—C4—C5	123.8 (9)	F6—C20—C21	117.8 (8)
F3—C4—C5	118.6 (8)	C22—C21—C20	116.5 (8)
C4—C5—C6	117.6 (8)	C22—C21—H21	121.7
C4—C5—H5	121.2	C20—C21—H21	121.7
C6—C5—H5	121.2	C21—C22—C17	121.0 (7)
C5—C6—C1	119.8 (7)	C21—C22—C23	120.6 (6)
C5—C6—C7	121.3 (6)	C17—C22—C23	118.4 (6)
C1—C6—C7	118.9 (7)	C32—C23—C24	118.1 (6)
C8—C7—C16	117.6 (6)	C32—C23—C22	122.3 (6)
C8—C7—C6	120.9 (6)	C24—C23—C22	119.5 (6)
C16—C7—C6	121.4 (7)	C23—C24—C25	120.7 (6)
C7—C8—C9	123.7 (7)	C23—C24—H24	119.7
C7—C8—H8	118.1	C25—C24—H24	119.7
C9—C8—H8	118.1	C30—C25—C24	120.8 (7)
C14—C9—C10	119.0 (7)	C30—C25—C26	118.7 (6)
C14—C9—C8	118.1 (7)	C24—C25—C26	120.6 (6)
C10—C9—C8	122.9 (7)	C27—C26—C25	119.0 (7)
C11—C10—C9	120.5 (7)	C27—C26—H26	120.5
C11—C10—H10	119.8	C25—C26—H26	120.5
C9—C10—H10	119.8	C28—C27—C26	122.1 (8)
C10—C11—C12	121.5 (8)	C28—C27—H27	119.0
C10—C11—H11	119.2	C26—C27—H27	119.0
C12—C11—H11	119.2	C27—C28—C29	120.2 (7)
C13—C12—C11	120.9 (8)	C27—C28—H28	119.9
C13—C12—H12	119.6	C29—C28—H28	119.9
C11—C12—H12	119.6	C28—C29—C30	120.1 (7)
C12—C13—C14	119.0 (7)	C28—C29—H29	119.9
C12—C13—H13	120.5	C30—C29—H29	119.9
C14—C13—H13	120.5	C25—C30—C29	119.9 (7)
C9—C14—C13	119.1 (7)	C25—C30—C31	118.2 (6)
C9—C14—C15	119.3 (6)	C29—C30—C31	121.9 (6)
C13—C14—C15	121.6 (6)	C32—C31—C30	119.7 (6)
C16—C15—C14	118.8 (6)	C32—C31—C15	120.0 (6)
C16—C15—C31	121.2 (6)	C30—C31—C15	120.2 (6)
C14—C15—C31	119.9 (6)	C31—C32—O2	121.9 (6)
O1—C16—C15	120.2 (6)	C31—C32—C23	122.5 (7)
O1—C16—C7	117.3 (6)	O2—C32—C23	115.6 (5)
C6—C1—C2—C3	0.2 (14)	F4—C18—C19—C20	−179.5 (8)
C6—C1—C2—F1	−179.9 (8)	C17—C18—C19—C20	1.0 (16)
C1—C2—C3—C4	0.2 (16)	F4—C18—C19—F5	−0.6 (15)
F1—C2—C3—C4	−179.7 (8)	C17—C18—C19—F5	179.9 (7)
C1—C2—C3—F2	−179.5 (8)	C18—C19—C20—F6	177.8 (10)
F1—C2—C3—F2	0.6 (15)	F5—C19—C20—F6	−1.2 (15)
F2—C3—C4—F3	1.8 (14)	C18—C19—C20—C21	−2.6 (16)
C2—C3—C4—F3	−177.9 (9)	F5—C19—C20—C21	178.4 (9)
F2—C3—C4—C5	178.9 (8)	C19—C20—C21—C22	1.7 (15)
C2—C3—C4—C5	−0.8 (15)	F6—C20—C21—C22	−178.7 (10)
C3—C4—C5—C6	0.9 (13)	C20—C21—C22—C17	0.8 (15)
F3—C4—C5—C6	178.0 (8)	C20—C21—C22—C23	179.4 (7)
C4—C5—C6—C1	−0.5 (12)	C18—C17—C22—C21	−2.3 (13)
C4—C5—C6—C7	178.1 (7)	C18—C17—C22—C23	179.0 (7)
C2—C1—C6—C5	0.0 (12)	C21—C22—C23—C32	57.0 (12)
C2—C1—C6—C7	−178.7 (7)	C17—C22—C23—C32	−124.4 (8)
C5—C6—C7—C8	−138.5 (8)	C21—C22—C23—C24	−127.2 (9)
C1—C6—C7—C8	40.1 (11)	C17—C22—C23—C24	51.5 (10)
C5—C6—C7—C16	43.8 (11)	C32—C23—C24—C25	0.1 (9)
C1—C6—C7—C16	−137.5 (7)	C22—C23—C24—C25	−175.9 (6)
C16—C7—C8—C9	2.7 (11)	C23—C24—C25—C30	−0.1 (10)
C6—C7—C8—C9	−175.0 (6)	C23—C24—C25—C26	−179.4 (6)
C7—C8—C9—C14	−3.1 (10)	C30—C25—C26—C27	0.0 (10)
C7—C8—C9—C10	177.0 (7)	C24—C25—C26—C27	179.3 (7)
C14—C9—C10—C11	0.2 (11)	C25—C26—C27—C28	−2.3 (12)
C8—C9—C10—C11	−179.9 (7)	C26—C27—C28—C29	3.2 (13)
C9—C10—C11—C12	−1.1 (12)	C27—C28—C29—C30	−1.7 (11)
C10—C11—C12—C13	0.2 (13)	C24—C25—C30—C29	−178.0 (6)
C11—C12—C13—C14	1.4 (12)	C26—C25—C30—C29	1.3 (10)
C10—C9—C14—C13	1.4 (10)	C24—C25—C30—C31	0.6 (9)
C8—C9—C14—C13	−178.4 (7)	C26—C25—C30—C31	180.0 (6)
C10—C9—C14—C15	−178.5 (6)	C28—C29—C30—C25	−0.5 (10)
C8—C9—C14—C15	1.6 (9)	C28—C29—C30—C31	−179.1 (6)
C12—C13—C14—C9	−2.2 (11)	C25—C30—C31—C32	−1.2 (9)
C12—C13—C14—C15	177.7 (6)	C29—C30—C31—C32	177.4 (6)
C9—C14—C15—C16	0.1 (9)	C25—C30—C31—C15	174.7 (6)
C13—C14—C15—C16	−179.9 (7)	C29—C30—C31—C15	−6.7 (9)
C9—C14—C15—C31	176.9 (6)	C16—C15—C31—C32	−77.4 (8)
C13—C14—C15—C31	−3.0 (10)	C14—C15—C31—C32	105.8 (8)
C14—C15—C16—O1	176.4 (6)	C16—C15—C31—C30	106.6 (8)
C31—C15—C16—O1	−0.5 (9)	C14—C15—C31—C30	−70.1 (8)
C14—C15—C16—C7	−0.5 (9)	C30—C31—C32—O2	179.5 (6)
C31—C15—C16—C7	−177.3 (7)	C15—C31—C32—O2	3.5 (10)
C8—C7—C16—O1	−177.8 (6)	C30—C31—C32—C23	1.3 (10)
C6—C7—C16—O1	0.0 (10)	C15—C31—C32—C23	−174.6 (7)
C8—C7—C16—C15	−0.8 (10)	C24—C23—C32—C31	−0.7 (10)
C6—C7—C16—C15	176.9 (6)	C22—C23—C32—C31	175.2 (6)
C22—C17—C18—C19	1.5 (14)	C24—C23—C32—O2	−179.0 (6)
C22—C17—C18—F4	−178.0 (7)	C22—C23—C32—O2	−3.1 (10)