(1R,8R,11R)-3,3,11-Tri­methyl-6,6-ethyl­ene­dioxy­bi­cyclo­[6.3.0]­undecan-2-one and (1R,2R,8R,11R)-3,3,11-tri­methyl-6,6-ethylenedioxybicyclo[6.3.0]undecan-2-ol

The reduction of (1R,8R,11R)-3,3,11-tri­methyl-6,6-ethyl­ene­dioxy­bi­cyclo­[6.3.0]­undecan-2-one, C₁₆H₂₆O₃, (I), gave exclusively an alcohol, C₁₆H₂₈O₃, (II). The stereochemistry of the hydroxyl group in (II) was shown as R. The conformation around the eight-membered carbocycle in (I) differs markedly from that in (II).

S1. Comment

During the course of our synthetic studies of precapnelladiene, the terpenoid with an 8-membered carbocycle, we prepared a chiral (1R,8R,11R)-3,3,11-trimethylbicyclo[6.3.0]undecane-2,6-dione (Maeda & Inouye, 1994) as the synthetic intermediate. Because of flexible conformation of an 8-membered ring, it is important to clarify the conformational change of the 8-membered ring during the reaction. We wish to report here crystal structures of (1R,8R,11R)-3,3,11-trimethyl-6,6-ethylenedioxybicyclo[6.3.0]undecan-2-one (I), which was synthesized from the dione, and the corresponding alcohol (II). The stereochemistry of the hydroxyl group in (II) was unequivocally confirmed as R as estimated from its NMR spectrum; the H attached at the alcoholic carbon absorbs at δ 3.56 with J=3.1 Hz. Two independent molecules were found in (II), they differ only in their conformations around an acetal moiety. On the other hand, the conformation of the 8-membered carbocycle differs markedly in (I) and (II). Torsion angles of the model indicate major differences being found at the carbons 4 and 5. Crystal structure of (I) reveals that the Re-side of the carbonyl carbon is protected by the C6-methylene group from an incoming reagent to give an R alcohol exclusively. The resulting alcoholic oxygen in (II) interacts with C6-methylene group giving conformational change at the carbons 4 and 5.

S2. Experimental

(1R,8R,11R)-3,11,11-Trimethylbicyclo[6.3.0]undecane-2,6-dione (Maeda & Inouye, 1997) was treated with tert-butyldimethylsilyl trifluoromethanesulfonate and 1,2-bis(trimethylsilyloxy)ethane at 203 K for 2 h, followed by a further 2 h at room temperature. The solution was filtered through a short silica-gel column with chloroform. After evaporating the solvent, the residue was chromatographed on alumina (benzene) to give (I) in 94% yield. (I) was reduced with LiAlH₄ in dry tetrahydrofuran at 273 K to afford (II) in 96% yield. Compound (I): m.p. 361–362 K (from hexane); found: C 72.35, H 9.67%; calculated for C₁₆H₂₆O₃: C 72.14, H 9.84%. Compound (2): m.p. 418–420 K (from hexane); found: C 71.76, H 10.66%; calculated for C₁₆H₂₈O₃: C 71.60, H 10.52%.

S3. Refinement

In (II), atoms C17B and C17C (0.50:0.50) were disordered. The positions of all the H atoms, except methyl H and disordered methylene H atoms, were refined in the final calculations. The methyl and the methylene H atoms were calculated geometrically. Friedel pairs were not measured for (I) and a few (229) for (II). Refinement of the absolute structure parameter is meaningless for this combination of chemical composition and X-ray wavelength; the absolute configurations are deduced from those of the chemical precursors.

Computing details

For both compounds, data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software (Enraf-Nonius, 1989); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL93 (Sheldrick, 1993).

(I) (1R,8R,11R)-3,3,11-Trimethyl-6,6-ethylenedioxybicyclo[6.3.0]undecan-2-one

Crystal data

C16H26O3	Dx = 1.184 Mg m^−3
Mr = 266.37	Melting point = 361–362 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 15.594 (3) Å	Cell parameters from 25 reflections
b = 16.837 (2) Å	θ = 10.0–13.6°
c = 5.6919 (8) Å	µ = 0.08 mm^−1
V = 1494.4 (4) Å^3	T = 293 K
Z = 4	Needle, colourless
F(000) = 584	0.50 × 0.20 × 0.20 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 30.5°, θmin = 1.8°
Graphite monochromator	h = 0→22
ω–2θ scans	k = 0→24
2616 measured reflections	l = 0→8
2616 independent reflections	3 standard reflections every 120 min
1316 reflections with I > 2σ(I)	intensity decay: 5.1%

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.1375P)^2] where P = (Fo^2 + 2Fc^2)/3
2616 reflections	(Δ/σ)max = 0.005
243 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

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.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _refine_ls_R_factor_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	0.0939 (3)	0.1546 (2)	0.0449 (8)	0.0401 (9)
H1	0.079 (3)	0.174 (2)	−0.093 (9)	0.033 (11)*
C2	0.0153 (3)	0.1583 (3)	0.2012 (7)	0.0434 (9)
C3	−0.0642 (3)	0.2008 (3)	0.1090 (8)	0.0497 (11)
C4	−0.0418 (4)	0.2782 (3)	−0.0232 (10)	0.0616 (13)
H4A	−0.003 (4)	0.269 (3)	−0.183 (12)	0.076 (17)*
H4B	−0.106 (5)	0.298 (4)	−0.062 (15)	0.11 (2)*
C5	0.0053 (5)	0.3437 (4)	0.1119 (12)	0.076 (2)
H5A	−0.018 (4)	0.350 (3)	0.290 (13)	0.073 (16)*
H5B	−0.013 (4)	0.390 (5)	0.060 (15)	0.11 (2)*
C6	0.1029 (4)	0.3440 (3)	0.1102 (9)	0.0613 (14)
C7	0.1445 (4)	0.2828 (3)	0.2711 (10)	0.0585 (13)
H7A	0.194 (4)	0.307 (3)	0.289 (12)	0.074 (17)*
H7B	0.108 (3)	0.275 (3)	0.426 (10)	0.053 (13)*
C8	0.1673 (3)	0.2030 (3)	0.1597 (9)	0.0502 (11)
H8	0.200 (3)	0.207 (3)	0.039 (10)	0.048 (13)*
C9	0.2080 (4)	0.1444 (4)	0.3337 (12)	0.071 (2)
H9A	0.182 (4)	0.151 (3)	0.499 (14)	0.079 (18)*
H9B	0.266 (4)	0.151 (3)	0.354 (11)	0.074 (17)*
C10	0.1874 (4)	0.0618 (4)	0.2433 (13)	0.071 (2)
H10A	0.235 (5)	0.031 (4)	0.240 (15)	0.10 (2)*
H10B	0.157 (4)	0.038 (3)	0.353 (11)	0.061 (17)*
C11	0.1350 (3)	0.0721 (3)	0.0209 (9)	0.0509 (11)
H11	0.176 (2)	0.078 (2)	−0.107 (8)	0.025 (9)*
O12	0.0156 (2)	0.1274 (2)	0.3950 (6)	0.0616 (10)
C13	−0.1064 (4)	0.1418 (4)	−0.0611 (10)	0.0699 (15)
H13A	−0.1597	0.1634	−0.1164	0.105*
H13B	−0.1170	0.0926	0.0189	0.105*
H13C	−0.0689	0.1326	−0.1920	0.105*
C14	−0.1266 (3)	0.2166 (4)	0.3179 (10)	0.072 (2)
H14A	−0.1777	0.2417	0.2603	0.108*
H14B	−0.0993	0.2507	0.4304	0.108*
H14C	−0.1413	0.1671	0.3915	0.108*
O15	0.1365 (3)	0.3371 (2)	−0.1187 (6)	0.0677 (11)
C16	0.1498 (5)	0.4130 (4)	−0.2090 (12)	0.069 (2)
H16A	0.108 (3)	0.428 (3)	−0.311 (11)	0.059 (15)*
H16B	0.203 (5)	0.406 (4)	−0.272 (13)	0.08 (2)*
C17	0.1468 (6)	0.4677 (4)	−0.0039 (14)	0.085 (2)
H17A	0.212 (6)	0.480 (5)	0.027 (18)	0.14 (3)*
H17B	0.136 (5)	0.512 (5)	0.032 (17)	0.12 (3)*
O18	0.1318 (4)	0.4204 (2)	0.1927 (7)	0.090 (2)
C19	0.0740 (4)	0.0043 (3)	−0.0378 (13)	0.074 (2)
H19A	0.0462	0.0150	−0.1850	0.112*
H19B	0.0316	−0.0003	0.0837	0.112*
H19C	0.1057	−0.0444	−0.0491	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.042 (2)	0.042 (2)	0.036 (2)	0.005 (2)	0.003 (2)	0.008 (2)
C2	0.048 (2)	0.049 (2)	0.034 (2)	0.004 (2)	0.001 (2)	0.003 (2)
C3	0.047 (2)	0.072 (3)	0.030 (2)	0.011 (2)	0.000 (2)	0.000 (2)
C4	0.067 (3)	0.071 (3)	0.047 (3)	0.028 (3)	−0.004 (3)	0.006 (3)
C5	0.113 (5)	0.052 (3)	0.063 (4)	0.027 (3)	0.002 (4)	−0.003 (3)
C6	0.101 (4)	0.044 (2)	0.039 (2)	−0.003 (2)	0.012 (3)	−0.008 (2)
C7	0.068 (3)	0.060 (3)	0.047 (3)	−0.007 (3)	0.009 (3)	−0.003 (2)
C8	0.048 (2)	0.057 (3)	0.046 (3)	−0.003 (2)	0.002 (2)	0.003 (2)
C9	0.045 (3)	0.089 (4)	0.080 (4)	0.011 (3)	−0.009 (3)	0.009 (4)
C10	0.071 (4)	0.069 (4)	0.072 (4)	0.021 (3)	−0.005 (3)	0.017 (3)
C11	0.053 (2)	0.045 (2)	0.054 (3)	0.010 (2)	0.011 (2)	0.009 (2)
O12	0.055 (2)	0.086 (2)	0.044 (2)	0.013 (2)	0.013 (2)	0.023 (2)
C13	0.057 (3)	0.099 (4)	0.054 (3)	0.003 (3)	−0.011 (2)	−0.010 (3)
C14	0.051 (3)	0.114 (4)	0.050 (3)	0.028 (3)	0.003 (2)	−0.005 (3)
O15	0.110 (3)	0.052 (2)	0.042 (2)	−0.010 (2)	0.019 (2)	−0.003 (2)
C16	0.094 (5)	0.061 (3)	0.054 (3)	0.000 (3)	0.004 (4)	0.012 (3)
C17	0.132 (6)	0.049 (3)	0.075 (4)	−0.021 (4)	0.001 (5)	0.002 (3)
O18	0.173 (5)	0.048 (2)	0.050 (2)	−0.020 (3)	0.000 (3)	−0.010 (2)
C19	0.088 (4)	0.048 (3)	0.087 (4)	0.003 (2)	0.012 (4)	−0.003 (3)

Geometric parameters (Å, º)

C1—C2	1.515 (6)	C9—H9A	1.03 (8)
C1—C11	1.537 (6)	C9—H9B	0.91 (6)
C1—C8	1.550 (7)	C10—C11	1.516 (8)
C1—H1	0.88 (5)	C10—H10A	0.90 (7)
C2—O12	1.220 (5)	C10—H10B	0.88 (6)
C2—C3	1.524 (6)	C11—C19	1.522 (8)
C3—C13	1.535 (7)	C11—H11	0.97 (4)
C3—C4	1.545 (7)	C13—H13A	0.96
C3—C14	1.559 (7)	C13—H13B	0.96
C4—C5	1.531 (9)	C13—H13C	0.96
C4—H4A	1.11 (6)	C14—H14A	0.96
C4—H4B	1.08 (7)	C14—H14B	0.96
C5—C6	1.521 (9)	C14—H14C	0.96
C5—H5A	1.08 (7)	O15—C16	1.393 (7)
C5—H5B	0.88 (8)	C16—C17	1.487 (10)
C6—O15	1.410 (6)	C16—H16A	0.91 (6)
C6—O18	1.441 (6)	C16—H16B	0.91 (7)
C6—C7	1.525 (8)	C17—O18	1.393 (8)
C7—C8	1.528 (7)	C17—H17A	1.05 (9)
C7—H7A	0.88 (6)	C17—H17B	0.79 (8)
C7—H7B	1.06 (5)	C19—H19A	0.96
C8—C9	1.535 (8)	C19—H19B	0.96
C8—H8	0.86 (5)	C19—H19C	0.96
C9—C10	1.517 (9)
C2—C1—C11	115.3 (4)	C10—C9—H9B	111 (3)
C2—C1—C8	109.2 (4)	C8—C9—H9B	115 (4)
C11—C1—C8	101.8 (4)	H9A—C9—H9B	105 (6)
C2—C1—H1	107 (3)	C11—C10—C9	107.1 (5)
C11—C1—H1	111 (3)	C11—C10—H10A	119 (6)
C8—C1—H1	112 (3)	C9—C10—H10A	111 (4)
O12—C2—C1	120.7 (4)	C11—C10—H10B	110 (4)
O12—C2—C3	121.0 (4)	C9—C10—H10B	107 (4)
C1—C2—C3	118.4 (4)	H10A—C10—H10B	102 (6)
C2—C3—C13	105.2 (4)	C10—C11—C19	115.8 (5)
C2—C3—C4	112.3 (4)	C10—C11—C1	104.7 (4)
C13—C3—C4	109.6 (4)	C19—C11—C1	115.9 (4)
C2—C3—C14	109.0 (4)	C10—C11—H11	107 (2)
C13—C3—C14	108.9 (4)	C19—C11—H11	109 (2)
C4—C3—C14	111.6 (4)	C1—C11—H11	105 (2)
C5—C4—C3	118.1 (5)	C3—C13—H13A	109.5
C5—C4—H4A	105 (3)	C3—C13—H13B	109.5
C3—C4—H4A	114 (3)	H13A—C13—H13B	109.5
C5—C4—H4B	109 (4)	C3—C13—H13C	109.5
C3—C4—H4B	99 (4)	H13A—C13—H13C	109.5
H4A—C4—H4B	113 (5)	H13B—C13—H13C	109.5
C6—C5—C4	118.6 (5)	C3—C14—H14A	109.5
C6—C5—H5A	110 (3)	C3—C14—H14B	109.5
C4—C5—H5A	113 (3)	H14A—C14—H14B	109.5
C6—C5—H5B	108 (5)	C3—C14—H14C	109.5
C4—C5—H5B	108 (5)	H14A—C14—H14C	109.5
H5A—C5—H5B	97 (6)	H14B—C14—H14C	109.5
O15—C6—O18	105.0 (4)	C16—O15—C6	108.7 (4)
O15—C6—C5	112.2 (5)	O15—C16—C17	105.9 (5)
O18—C6—C5	108.3 (5)	O15—C16—H16A	113 (3)
O15—C6—C7	109.9 (4)	C17—C16—H16A	108 (3)
O18—C6—C7	106.0 (5)	O15—C16—H16B	100 (4)
C5—C6—C7	114.8 (5)	C17—C16—H16B	115 (4)
C6—C7—C8	116.4 (4)	H16A—C16—H16B	116 (5)
C6—C7—H7A	98 (4)	O18—C17—C16	106.4 (5)
C8—C7—H7A	104 (4)	O18—C17—H17A	98 (5)
C6—C7—H7B	111 (3)	C16—C17—H17A	103 (6)
C8—C7—H7B	111 (3)	O18—C17—H17B	107 (7)
H7A—C7—H7B	116 (5)	C16—C17—H17B	143 (7)
C7—C8—C9	113.2 (5)	H17A—C17—H17B	89 (7)
C7—C8—C1	117.7 (4)	C17—O18—C6	107.5 (4)
C9—C8—C1	103.9 (4)	C11—C19—H19A	109.5
C7—C8—H8	114 (3)	C11—C19—H19B	109.5
C9—C8—H8	108 (3)	H19A—C19—H19B	109.5
C1—C8—H8	98 (3)	C11—C19—H19C	109.5
C10—C9—C8	106.4 (5)	H19A—C19—H19C	109.5
C10—C9—H9A	109 (3)	H19B—C19—H19C	109.5
C8—C9—H9A	111 (4)
C11—C1—C2—O12	47.5 (6)	C2—C1—C8—C7	−42.0 (5)
C8—C1—C2—O12	−66.2 (5)	C11—C1—C8—C7	−164.3 (4)
C11—C1—C2—C3	−131.8 (4)	C2—C1—C8—C9	83.9 (5)
C8—C1—C2—C3	114.4 (4)	C11—C1—C8—C9	−38.3 (5)
O12—C2—C3—C13	−101.2 (5)	C7—C8—C9—C10	153.0 (5)
C1—C2—C3—C13	78.1 (5)	C1—C8—C9—C10	24.3 (6)
O12—C2—C3—C4	139.6 (5)	C8—C9—C10—C11	−0.3 (7)
C1—C2—C3—C4	−41.1 (5)	C9—C10—C11—C19	−152.9 (5)
O12—C2—C3—C14	15.4 (6)	C9—C10—C11—C1	−24.0 (6)
C1—C2—C3—C14	−165.3 (4)	C2—C1—C11—C10	−79.6 (5)
C2—C3—C4—C5	−60.3 (6)	C8—C1—C11—C10	38.4 (5)
C13—C3—C4—C5	−176.9 (5)	C2—C1—C11—C19	49.2 (7)
C14—C3—C4—C5	62.4 (6)	C8—C1—C11—C19	167.2 (5)
C3—C4—C5—C6	90.5 (7)	O18—C6—O15—C16	−25.2 (7)
C4—C5—C6—O15	49.6 (8)	C5—C6—O15—C16	92.2 (6)
C4—C5—C6—O18	165.0 (5)	C7—C6—O15—C16	−138.8 (5)
C4—C5—C6—C7	−76.8 (7)	C6—O15—C16—C17	15.9 (8)
O15—C6—C7—C8	−34.4 (7)	O15—C16—C17—O18	−0.1 (9)
O18—C6—C7—C8	−147.3 (5)	C16—C17—O18—C6	−15.2 (8)
C5—C6—C7—C8	93.2 (6)	O15—C6—O18—C17	24.9 (7)
C6—C7—C8—C9	−179.4 (5)	C5—C6—O18—C17	−95.1 (7)
C6—C7—C8—C1	−58.1 (6)	C7—C6—O18—C17	141.2 (6)

(II) (1R,2R,8R,11R)-3,3,11-Trimethyl-6,6-ethylenedioxybicyclo[6.3.0]undecan-2-ol

Crystal data

C16H28O3	Dx = 1.153 Mg m^−3
Mr = 268.38	Melting point = 418–420 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.368 (3) Å	Cell parameters from 25 reflections
b = 16.3349 (14) Å	θ = 11.6–14.0°
c = 10.211 (3) Å	µ = 0.08 mm^−1
β = 116.614 (12)°	T = 293 K
V = 1546.1 (7) Å^3	Needle, colourless
Z = 4	0.70 × 0.30 × 0.20 mm
F(000) = 592

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.013
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.2°
Graphite monochromator	h = −14→13
ω–2θ scans	k = 0→22
4876 measured reflections	l = 0→14
4647 independent reflections	3 standard reflections every 120 min
3562 reflections with I > 2σ(I)	intensity decay: 3.0%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0713P)^2 + 0.0858P] where P = (Fo^2 + 2Fc^2)/3
4647 reflections	(Δ/σ)max = −0.001
503 parameters	Δρmax = 0.22 e Å^−3
1 restraint	Δρmin = −0.15 e Å^−3

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.

Refinement. Refinement on F² for ALL reflections except for 2 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _refine_ls_R_factor_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	Occ. (<1)
C1A	0.2767 (2)	0.1517 (2)	1.0441 (3)	0.0381 (5)
H1A	0.345 (3)	0.1231 (17)	1.128 (3)	0.034 (6)*
C2A	0.1284 (2)	0.1114 (2)	1.0032 (2)	0.0390 (5)
H2A	0.087 (3)	0.1371 (17)	1.062 (3)	0.039 (7)*
C3A	0.1291 (2)	0.0197 (2)	1.0409 (3)	0.0430 (5)
C4A	0.1874 (3)	−0.0392 (2)	0.9622 (3)	0.0479 (6)
H4A1	0.129 (3)	−0.034 (2)	0.855 (4)	0.049 (8)*
H4A2	0.169 (4)	−0.090 (2)	0.996 (4)	0.053 (8)*
C5A	0.3478 (3)	−0.0326 (2)	0.9962 (3)	0.0473 (6)
H5A1	0.394 (3)	−0.086 (2)	1.008 (3)	0.049 (8)*
H5A2	0.407 (4)	0.001 (2)	1.085 (4)	0.055 (8)*
C6A	0.3724 (2)	0.0056 (2)	0.8741 (3)	0.0442 (5)
C7A	0.2950 (3)	0.0855 (2)	0.8140 (3)	0.0445 (6)
H7A1	0.323 (4)	0.103 (2)	0.741 (4)	0.058 (9)*
H7A2	0.195 (4)	0.077 (2)	0.766 (3)	0.049 (8)*
C8A	0.3275 (3)	0.1558 (2)	0.9224 (3)	0.0414 (5)
H8A	0.430 (3)	0.161 (2)	0.970 (3)	0.049 (8)*
C9A	0.2675 (4)	0.2378 (2)	0.8426 (4)	0.0623 (8)
H9A1	0.176 (5)	0.227 (3)	0.746 (5)	0.087 (13)*
H9A2	0.342 (4)	0.265 (3)	0.837 (4)	0.075 (11)*
C10A	0.2209 (5)	0.2881 (2)	0.9383 (4)	0.0665 (8)
H10A	0.254 (4)	0.344 (3)	0.949 (4)	0.066 (10)*
H10B	0.111 (6)	0.285 (3)	0.892 (6)	0.108 (16)*
C11A	0.2841 (3)	0.2438 (2)	1.0862 (3)	0.0509 (6)
H11A	0.390 (4)	0.255 (2)	1.134 (4)	0.066 (10)*
O12A	0.0348 (2)	0.12714 (14)	0.8513 (2)	0.0519 (5)
H12A	−0.037 (4)	0.142 (2)	0.855 (4)	0.069 (11)*
C13A	0.2118 (3)	0.0090 (2)	1.2071 (3)	0.0549 (7)
H13A	0.2024	−0.0465	1.2325	0.082*
H13B	0.1730	0.0454	1.2543	0.082*
H13C	0.3119	0.0214	1.2387	0.082*
C14A	−0.0289 (3)	−0.0053 (2)	0.9942 (4)	0.0601 (7)
H14A	−0.0323	−0.0613	1.0208	0.090*
H14B	−0.0836	0.0008	0.8901	0.090*
H14C	−0.0693	0.0291	1.0427	0.090*
O15A	0.5262 (2)	0.01540 (14)	0.9269 (2)	0.0536 (5)
C16A	0.5639 (3)	−0.0118 (3)	0.8181 (4)	0.0613 (8)
H16A	0.605 (5)	0.036 (3)	0.787 (5)	0.090 (13)*
H16B	0.644 (6)	−0.040 (4)	0.845 (5)	0.099 (15)*
C17A	0.4330 (5)	−0.0531 (4)	0.7049 (6)	0.095 (2)
H17A	0.438 (5)	−0.103 (3)	0.667 (5)	0.079 (12)*
H17B	0.403 (14)	0.007 (9)	0.615 (14)	0.29 (6)*
O18A	0.3308 (2)	−0.0520 (2)	0.7568 (2)	0.0604 (6)
C19A	0.2211 (4)	0.2682 (2)	1.1883 (4)	0.0714 (9)
H19A	0.2571	0.2323	1.2715	0.107*
H19B	0.1179	0.2643	1.1377	0.107*
H19C	0.2484	0.3235	1.2206	0.107*
C1B	0.8496 (2)	0.05100 (15)	0.4742 (2)	0.0352 (4)
H1B	0.929 (3)	0.0828 (17)	0.547 (3)	0.034 (6)*
C2B	0.8042 (2)	0.0891 (2)	0.3213 (2)	0.0364 (5)
H2B	0.863 (3)	0.0630 (18)	0.278 (3)	0.038 (7)*
C3B	0.8361 (2)	0.1816 (2)	0.3177 (2)	0.0403 (5)
C4B	0.7575 (3)	0.2393 (2)	0.3773 (3)	0.0427 (5)
H4B1	0.651 (4)	0.236 (2)	0.318 (3)	0.052 (8)*
H4B2	0.777 (3)	0.294 (2)	0.354 (3)	0.053 (8)*
C5B	0.7951 (3)	0.2336 (2)	0.5407 (3)	0.0427 (5)
H5B1	0.880 (3)	0.2019 (19)	0.592 (3)	0.042 (7)*
H5B2	0.804 (3)	0.290 (2)	0.573 (3)	0.043 (7)*
C6B	0.6788 (2)	0.1936 (2)	0.5709 (2)	0.0386 (5)
C7B	0.6218 (2)	0.1128 (2)	0.4952 (3)	0.0394 (5)
H7B1	0.555 (3)	0.096 (2)	0.533 (3)	0.055 (9)*
H7B2	0.571 (3)	0.1220 (19)	0.392 (4)	0.044 (7)*
C8B	0.7320 (2)	0.04458 (15)	0.5283 (2)	0.0375 (5)
H8B	0.785 (4)	0.040 (2)	0.634 (4)	0.055 (8)*
C9B	0.6574 (3)	−0.0389 (2)	0.4705 (4)	0.0530 (6)
H9B1	0.554 (5)	−0.027 (3)	0.383 (5)	0.075 (11)*
H9B2	0.640 (4)	−0.064 (2)	0.535 (4)	0.052 (9)*
C10B	0.7557 (4)	−0.0884 (2)	0.4278 (4)	0.0616 (8)
H10C	0.775 (4)	−0.145 (3)	0.471 (4)	0.063 (9)*
H10D	0.711 (5)	−0.088 (3)	0.309 (6)	0.097 (15)*
C11B	0.8970 (3)	−0.0400 (2)	0.4857 (3)	0.0476 (6)
H11B	0.950 (3)	−0.0518 (19)	0.596 (3)	0.043 (7)*
O12B	0.6550 (2)	0.07068 (13)	0.2301 (2)	0.0474 (4)
H12B	0.652 (4)	0.060 (2)	0.151 (4)	0.059 (9)*
C13B	0.9995 (3)	0.1953 (2)	0.3979 (3)	0.0544 (7)
H13D	1.0327	0.1870	0.5010	0.082*
H13E	1.0213	0.2502	0.3807	0.082*
H13F	1.0468	0.1572	0.3621	0.082*
C14B	0.7856 (4)	0.2053 (2)	0.1564 (3)	0.0576 (7)
H14D	0.8257	0.1678	0.1121	0.086*
H14E	0.8173	0.2599	0.1511	0.086*
H14F	0.6822	0.2030	0.1054	0.086*
O15B	0.7346 (2)	0.18407 (12)	0.7278 (2)	0.0481 (4)
C16B	0.6475 (6)	0.2286 (3)	0.7742 (4)	0.090 (2)
H16C	0.659 (7)	0.228 (4)	0.856 (7)	0.13 (2)*
H16D	0.750 (7)	0.264 (5)	0.817 (7)	0.14 (2)*
C17B	0.5121 (10)	0.2504 (7)	0.6323 (9)	0.068 (2)	0.50
H17C	0.4361	0.2105	0.6113	0.082*	0.50
H17D	0.4762	0.3043	0.6391	0.082*	0.50
C17C	0.5746 (10)	0.2893 (5)	0.6584 (9)	0.064 (2)	0.50
H17E	0.4812	0.3039	0.6519	0.077*	0.50
H17F	0.6325	0.3385	0.6759	0.077*	0.50
O18B	0.5595 (2)	0.24882 (14)	0.5293 (2)	0.0574 (5)
C19B	0.9960 (4)	−0.0632 (2)	0.4180 (5)	0.0716 (9)
H19D	1.0746	−0.0251	0.4491	0.107*
H19E	0.9428	−0.0619	0.3132	0.107*
H19F	1.0332	−0.1174	0.4490	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0290 (9)	0.0473 (13)	0.0330 (10)	−0.0007 (9)	0.0094 (8)	0.0014 (9)
C2A	0.0277 (9)	0.0536 (14)	0.0335 (10)	0.0033 (9)	0.0116 (8)	0.0014 (10)
C3A	0.0327 (10)	0.0537 (15)	0.0424 (12)	−0.0064 (10)	0.0167 (9)	0.0006 (10)
C4A	0.0438 (13)	0.0471 (15)	0.056 (2)	−0.0088 (11)	0.0247 (12)	−0.0043 (12)
C5A	0.0406 (12)	0.052 (2)	0.0476 (14)	0.0037 (11)	0.0185 (11)	0.0009 (12)
C6A	0.0324 (10)	0.0580 (15)	0.0411 (12)	−0.0045 (10)	0.0155 (9)	−0.0117 (11)
C7A	0.0361 (11)	0.062 (2)	0.0336 (11)	−0.0019 (11)	0.0145 (9)	−0.0003 (11)
C8A	0.0341 (11)	0.0485 (13)	0.0408 (12)	−0.0025 (10)	0.0160 (9)	0.0013 (10)
C9A	0.077 (2)	0.058 (2)	0.058 (2)	0.004 (2)	0.036 (2)	0.0116 (15)
C10A	0.083 (2)	0.049 (2)	0.067 (2)	0.006 (2)	0.033 (2)	0.0043 (15)
C11A	0.0503 (14)	0.0496 (15)	0.0503 (14)	−0.0060 (12)	0.0203 (12)	−0.0064 (12)
O12A	0.0283 (8)	0.0784 (14)	0.0392 (9)	0.0078 (8)	0.0064 (7)	0.0082 (9)
C13A	0.0550 (15)	0.070 (2)	0.0433 (13)	0.0036 (14)	0.0253 (12)	0.0108 (13)
C14A	0.0410 (14)	0.073 (2)	0.069 (2)	−0.0137 (13)	0.0275 (13)	−0.001 (2)
O15A	0.0294 (8)	0.0804 (14)	0.0493 (10)	−0.0035 (9)	0.0162 (7)	−0.0167 (10)
C16A	0.0472 (15)	0.082 (2)	0.063 (2)	−0.002 (2)	0.0324 (14)	−0.014 (2)
C17A	0.071 (2)	0.125 (4)	0.111 (3)	−0.034 (2)	0.059 (2)	−0.072 (3)
O18A	0.0477 (10)	0.0784 (14)	0.0571 (12)	−0.0143 (10)	0.0252 (9)	−0.0283 (11)
C19A	0.089 (2)	0.064 (2)	0.069 (2)	−0.007 (2)	0.042 (2)	−0.019 (2)
C1B	0.0299 (9)	0.0408 (12)	0.0291 (10)	−0.0001 (8)	0.0080 (8)	−0.0018 (9)
C2B	0.0312 (9)	0.0483 (13)	0.0277 (9)	−0.0016 (9)	0.0114 (8)	−0.0035 (9)
C3B	0.0389 (11)	0.0518 (14)	0.0294 (10)	−0.0050 (10)	0.0145 (9)	0.0014 (10)
C4B	0.0473 (13)	0.0392 (12)	0.0414 (12)	0.0007 (10)	0.0197 (10)	0.0053 (10)
C5B	0.0457 (12)	0.0409 (13)	0.0403 (12)	−0.0030 (11)	0.0181 (10)	−0.0060 (10)
C6B	0.0366 (10)	0.0476 (13)	0.0296 (9)	0.0101 (10)	0.0130 (8)	0.0013 (9)
C7B	0.0321 (10)	0.0508 (14)	0.0347 (11)	−0.0011 (10)	0.0144 (9)	0.0003 (10)
C8B	0.0375 (11)	0.0424 (12)	0.0300 (11)	−0.0028 (9)	0.0130 (9)	−0.0001 (9)
C9B	0.055 (2)	0.0473 (15)	0.061 (2)	−0.0119 (13)	0.0292 (14)	−0.0013 (13)
C10B	0.064 (2)	0.041 (2)	0.077 (2)	−0.0031 (13)	0.028 (2)	−0.0061 (15)
C11B	0.0471 (13)	0.0478 (14)	0.0436 (13)	0.0095 (11)	0.0165 (11)	0.0041 (11)
O12B	0.0360 (8)	0.0693 (12)	0.0277 (8)	−0.0102 (8)	0.0060 (6)	−0.0073 (8)
C13B	0.0448 (13)	0.069 (2)	0.052 (2)	−0.0164 (13)	0.0244 (12)	−0.0037 (14)
C14B	0.068 (2)	0.070 (2)	0.0390 (13)	−0.002 (2)	0.0278 (13)	0.0116 (13)
O15B	0.0483 (9)	0.0645 (12)	0.0296 (8)	0.0146 (9)	0.0158 (7)	0.0010 (8)
C16B	0.120 (4)	0.106 (3)	0.052 (2)	0.056 (3)	0.045 (2)	0.009 (2)
C17B	0.072 (5)	0.075 (5)	0.070 (5)	0.032 (4)	0.043 (4)	0.008 (4)
C17C	0.076 (5)	0.054 (4)	0.065 (4)	0.023 (4)	0.033 (4)	−0.008 (3)
O18B	0.0507 (10)	0.0700 (13)	0.0475 (10)	0.0277 (10)	0.0184 (8)	0.0086 (9)
C19B	0.070 (2)	0.070 (2)	0.082 (2)	0.026 (2)	0.040 (2)	0.006 (2)

Geometric parameters (Å, º)

C1A—C2A	1.547 (3)	C1B—C11B	1.554 (4)
C1A—C8A	1.554 (3)	C1B—H1B	0.97 (3)
C1A—C11A	1.557 (4)	C2B—O12B	1.435 (3)
C1A—H1A	0.96 (3)	C2B—C3B	1.552 (4)
C2A—O12A	1.437 (3)	C2B—H2B	1.00 (3)
C2A—C3A	1.546 (4)	C3B—C13B	1.532 (4)
C2A—H2A	0.98 (3)	C3B—C14B	1.537 (3)
C3A—C13A	1.530 (4)	C3B—C4B	1.538 (4)
C3A—C14A	1.542 (3)	C4B—C5B	1.536 (4)
C3A—C4A	1.541 (4)	C4B—H4B1	1.00 (3)
C4A—C5A	1.543 (4)	C4B—H4B2	0.97 (4)
C4A—H4A1	0.99 (3)	C5B—C6B	1.519 (4)
C4A—H4A2	0.95 (4)	C5B—H5B1	0.95 (3)
C5A—C6A	1.514 (4)	C5B—H5B2	0.96 (3)
C5A—H5A1	0.98 (3)	C6B—O18B	1.432 (3)
C5A—H5A2	1.00 (4)	C6B—O15B	1.448 (3)
C6A—O18A	1.430 (3)	C6B—C7B	1.510 (4)
C6A—O15A	1.445 (3)	C7B—C8B	1.522 (4)
C6A—C7A	1.510 (4)	C7B—H7B1	0.97 (3)
C7A—C8A	1.525 (4)	C7B—H7B2	0.95 (3)
C7A—H7A1	0.95 (3)	C8B—C9B	1.548 (4)
C7A—H7A2	0.94 (3)	C8B—H8B	0.97 (3)
C8A—C9A	1.546 (4)	C9B—C10B	1.510 (5)
C8A—H8A	0.95 (3)	C9B—H9B1	1.06 (4)
C9A—C10A	1.511 (5)	C9B—H9B2	0.86 (3)
C9A—H9A1	1.03 (5)	C10B—C11B	1.531 (4)
C9A—H9A2	0.92 (4)	C10B—H10C	1.00 (4)
C10A—C11A	1.532 (5)	C10B—H10D	1.09 (5)
C10A—H10A	0.97 (4)	C11B—C19B	1.520 (4)
C10A—H10B	1.02 (5)	C11B—H11B	1.03 (3)
C11A—C19A	1.511 (4)	O12B—H12B	0.82 (4)
C11A—H11A	1.00 (4)	C13B—H13D	0.96
O12A—H12A	0.79 (4)	C13B—H13E	0.96
C13A—H13A	0.96	C13B—H13F	0.96
C13A—H13B	0.96	C14B—H14D	0.96
C13A—H13C	0.96	C14B—H14E	0.96
C14A—H14A	0.96	C14B—H14F	0.96
C14A—H14B	0.96	O15B—C16B	1.397 (4)
C14A—H14C	0.96	C16B—C17C	1.468 (9)
O15A—C16A	1.405 (3)	C16B—C17B	1.542 (10)
C16A—C17A	1.493 (5)	C16B—H16C	0.78 (7)
C16A—H16A	1.01 (5)	C16B—H16D	1.11 (7)
C16A—H16B	0.88 (6)	C17B—O18B	1.346 (8)
C17A—O18A	1.381 (4)	C17B—H17C	0.97
C17A—H17A	0.92 (5)	C17B—H17D	0.97
C17A—H17B	1.28 (14)	C17C—O18B	1.419 (8)
C19A—H19A	0.96	C17C—H17E	0.97
C19A—H19B	0.96	C17C—H17F	0.97
C19A—H19C	0.96	C19B—H19D	0.96
C1B—C2B	1.545 (3)	C19B—H19E	0.96
C1B—C8B	1.551 (3)	C19B—H19F	0.96
C2A—C1A—C8A	117.0 (2)	C11B—C1B—H1B	108.7 (16)
C2A—C1A—C11A	113.9 (2)	O12B—C2B—C1B	108.9 (2)
C8A—C1A—C11A	100.7 (2)	O12B—C2B—C3B	111.6 (2)
C2A—C1A—H1A	106.1 (16)	C1B—C2B—C3B	116.4 (2)
C8A—C1A—H1A	111.4 (16)	O12B—C2B—H2B	108.5 (16)
C11A—C1A—H1A	107.4 (16)	C1B—C2B—H2B	108.0 (16)
O12A—C2A—C3A	111.5 (2)	C3B—C2B—H2B	103.1 (16)
O12A—C2A—C1A	108.9 (2)	C13B—C3B—C14B	107.5 (2)
C3A—C2A—C1A	116.9 (2)	C13B—C3B—C4B	110.8 (2)
O12A—C2A—H2A	108.5 (16)	C14B—C3B—C4B	106.4 (2)
C3A—C2A—H2A	102.4 (16)	C13B—C3B—C2B	109.0 (2)
C1A—C2A—H2A	108.2 (16)	C14B—C3B—C2B	107.2 (2)
C13A—C3A—C14A	107.6 (2)	C4B—C3B—C2B	115.5 (2)
C13A—C3A—C4A	110.5 (2)	C5B—C4B—C3B	118.1 (2)
C14A—C3A—C4A	106.5 (2)	C5B—C4B—H4B1	109.1 (18)
C13A—C3A—C2A	109.0 (2)	C3B—C4B—H4B1	111.6 (18)
C14A—C3A—C2A	107.1 (2)	C5B—C4B—H4B2	110.1 (19)
C4A—C3A—C2A	115.7 (2)	C3B—C4B—H4B2	105.1 (19)
C3A—C4A—C5A	118.3 (2)	H4B1—C4B—H4B2	102 (3)
C3A—C4A—H4A1	109.5 (19)	C6B—C5B—C4B	114.1 (2)
C5A—C4A—H4A1	107.7 (18)	C6B—C5B—H5B1	106.0 (18)
C3A—C4A—H4A2	100 (2)	C4B—C5B—H5B1	110.9 (17)
C5A—C4A—H4A2	111 (2)	C6B—C5B—H5B2	107.4 (17)
H4A1—C4A—H4A2	111 (3)	C4B—C5B—H5B2	104.7 (17)
C6A—C5A—C4A	113.9 (2)	H5B1—C5B—H5B2	114 (3)
C6A—C5A—H5A1	102.6 (18)	O18B—C6B—O15B	105.1 (2)
C4A—C5A—H5A1	112.4 (18)	O18B—C6B—C7B	108.1 (2)
C6A—C5A—H5A2	105.1 (19)	O15B—C6B—C7B	110.1 (2)
C4A—C5A—H5A2	113.9 (19)	O18B—C6B—C5B	109.1 (2)
H5A1—C5A—H5A2	108 (3)	O15B—C6B—C5B	108.1 (2)
O18A—C6A—O15A	104.7 (2)	C7B—C6B—C5B	115.8 (2)
O18A—C6A—C7A	108.8 (2)	C6B—C7B—C8B	116.4 (2)
O15A—C6A—C7A	110.6 (2)	C6B—C7B—H7B1	103 (2)
O18A—C6A—C5A	108.6 (2)	C8B—C7B—H7B1	108 (2)
O15A—C6A—C5A	107.6 (2)	C6B—C7B—H7B2	108.9 (19)
C7A—C6A—C5A	115.9 (2)	C8B—C7B—H7B2	110.5 (18)
C6A—C7A—C8A	116.8 (2)	H7B1—C7B—H7B2	110 (3)
C6A—C7A—H7A1	106 (2)	C7B—C8B—C9B	111.3 (2)
C8A—C7A—H7A1	107 (2)	C7B—C8B—C1B	120.2 (2)
C6A—C7A—H7A2	110 (2)	C9B—C8B—C1B	105.2 (2)
C8A—C7A—H7A2	109 (2)	C7B—C8B—H8B	107 (2)
H7A1—C7A—H7A2	107 (3)	C9B—C8B—H8B	107 (2)
C7A—C8A—C9A	111.4 (2)	C1B—C8B—H8B	105.3 (18)
C7A—C8A—C1A	120.3 (2)	C10B—C9B—C8B	107.2 (2)
C9A—C8A—C1A	105.0 (2)	C10B—C9B—H9B1	114 (2)
C7A—C8A—H8A	106 (2)	C8B—C9B—H9B1	108 (2)
C9A—C8A—H8A	106 (2)	C10B—C9B—H9B2	112 (2)
C1A—C8A—H8A	107.3 (18)	C8B—C9B—H9B2	111 (2)
C10A—C9A—C8A	107.4 (3)	H9B1—C9B—H9B2	105 (3)
C10A—C9A—H9A1	107 (3)	C9B—C10B—C11B	105.3 (2)
C8A—C9A—H9A1	110 (3)	C9B—C10B—H10C	114 (2)
C10A—C9A—H9A2	107 (3)	C11B—C10B—H10C	110 (2)
C8A—C9A—H9A2	108 (3)	C9B—C10B—H10D	108 (3)
H9A1—C9A—H9A2	118 (4)	C11B—C10B—H10D	106 (3)
C9A—C10A—C11A	105.1 (3)	H10C—C10B—H10D	113 (3)
C9A—C10A—H10A	113 (2)	C19B—C11B—C10B	114.8 (3)
C11A—C10A—H10A	111 (2)	C19B—C11B—C1B	117.4 (3)
C9A—C10A—H10B	107 (3)	C10B—C11B—C1B	104.4 (2)
C11A—C10A—H10B	109 (3)	C19B—C11B—H11B	108.0 (16)
H10A—C10A—H10B	111 (4)	C10B—C11B—H11B	106.2 (16)
C19A—C11A—C10A	115.4 (3)	C1B—C11B—H11B	105.1 (17)
C19A—C11A—C1A	117.5 (3)	C2B—O12B—H12B	104 (3)
C10A—C11A—C1A	103.8 (2)	C3B—C13B—H13D	109.5
C19A—C11A—H11A	110 (2)	C3B—C13B—H13E	109.5
C10A—C11A—H11A	107 (2)	H13D—C13B—H13E	109.5
C1A—C11A—H11A	103 (2)	C3B—C13B—H13F	109.5
C2A—O12A—H12A	101 (3)	H13D—C13B—H13F	109.5
C3A—C13A—H13A	109.5	H13E—C13B—H13F	109.5
C3A—C13A—H13B	109.5	C3B—C14B—H14D	109.5
H13A—C13A—H13B	109.5	C3B—C14B—H14E	109.5
C3A—C13A—H13C	109.5	H14D—C14B—H14E	109.5
H13A—C13A—H13C	109.5	C3B—C14B—H14F	109.5
H13B—C13A—H13C	109.5	H14D—C14B—H14F	109.5
C3A—C14A—H14A	109.5	H14E—C14B—H14F	109.5
C3A—C14A—H14B	109.5	C16B—O15B—C6B	108.7 (2)
H14A—C14A—H14B	109.5	O15B—C16B—C17C	104.8 (4)
C3A—C14A—H14C	109.5	O15B—C16B—C17B	104.9 (4)
H14A—C14A—H14C	109.5	O15B—C16B—H16C	123 (5)
H14B—C14A—H14C	109.5	C17C—C16B—H16C	130 (5)
C16A—O15A—C6A	108.8 (2)	C17B—C16B—H16C	130 (5)
O15A—C16A—C17A	106.0 (2)	O15B—C16B—H16D	76 (4)
O15A—C16A—H16A	108 (3)	C17C—C16B—H16D	91 (4)
C17A—C16A—H16A	118 (3)	C17B—C16B—H16D	124 (4)
O15A—C16A—H16B	119 (3)	H16C—C16B—H16D	85 (5)
C17A—C16A—H16B	114 (4)	O18B—C17B—C16B	103.4 (5)
H16A—C16A—H16B	92 (4)	O18B—C17B—H17C	111.1
O18A—C17A—C16A	106.6 (3)	C16B—C17B—H17C	111.1
O18A—C17A—H17A	112 (3)	O18B—C17B—H17D	111.1
C16A—C17A—H17A	122 (3)	C16B—C17B—H17D	111.1
O18A—C17A—H17B	107 (5)	H17C—C17B—H17D	109.0
C16A—C17A—H17B	93 (6)	O18B—C17C—C16B	103.6 (5)
H17A—C17A—H17B	115 (6)	O18B—C17C—H17E	111.0
C17A—O18A—C6A	109.5 (2)	C16B—C17C—H17E	111.0
C11A—C19A—H19A	109.5	O18B—C17C—H17F	111.0
C11A—C19A—H19B	109.5	C16B—C17C—H17F	111.0
H19A—C19A—H19B	109.5	H17E—C17C—H17F	109.0
C11A—C19A—H19C	109.5	C17B—O18B—C6B	110.5 (4)
H19A—C19A—H19C	109.5	C17C—O18B—C6B	107.3 (3)
H19B—C19A—H19C	109.5	C11B—C19B—H19D	109.5
C2B—C1B—C8B	117.1 (2)	C11B—C19B—H19E	109.5
C2B—C1B—C11B	113.9 (2)	H19D—C19B—H19E	109.5
C8B—C1B—C11B	100.4 (2)	C11B—C19B—H19F	109.5
C2B—C1B—H1B	109.0 (15)	H19D—C19B—H19F	109.5
C8B—C1B—H1B	107.2 (16)	H19E—C19B—H19F	109.5
C8A—C1A—C2A—O12A	−32.4 (3)	C1B—C2B—C3B—C13B	62.6 (3)
C11A—C1A—C2A—O12A	84.7 (3)	O12B—C2B—C3B—C14B	−55.5 (2)
C8A—C1A—C2A—C3A	95.1 (3)	C1B—C2B—C3B—C14B	178.7 (2)
C11A—C1A—C2A—C3A	−147.8 (2)	O12B—C2B—C3B—C4B	62.9 (2)
O12A—C2A—C3A—C13A	−171.6 (2)	C1B—C2B—C3B—C4B	−62.8 (3)
C1A—C2A—C3A—C13A	62.2 (3)	C13B—C3B—C4B—C5B	−59.4 (3)
O12A—C2A—C3A—C14A	−55.4 (3)	C14B—C3B—C4B—C5B	−176.0 (2)
C1A—C2A—C3A—C14A	178.4 (2)	C2B—C3B—C4B—C5B	65.1 (3)
O12A—C2A—C3A—C4A	63.2 (3)	C3B—C4B—C5B—C6B	−106.9 (3)
C1A—C2A—C3A—C4A	−63.0 (3)	C4B—C5B—C6B—O18B	−72.5 (3)
C13A—C3A—C4A—C5A	−59.3 (3)	C4B—C5B—C6B—O15B	173.7 (2)
C14A—C3A—C4A—C5A	−176.0 (3)	C4B—C5B—C6B—C7B	49.7 (3)
C2A—C3A—C4A—C5A	65.1 (3)	O18B—C6B—C7B—C8B	−178.5 (2)
C3A—C4A—C5A—C6A	−106.6 (3)	O15B—C6B—C7B—C8B	−64.3 (3)
C4A—C5A—C6A—O18A	−73.0 (3)	C5B—C6B—C7B—C8B	58.7 (3)
C4A—C5A—C6A—O15A	174.2 (2)	C6B—C7B—C8B—C9B	168.5 (2)
C4A—C5A—C6A—C7A	49.8 (3)	C6B—C7B—C8B—C1B	−68.0 (3)
O18A—C6A—C7A—C8A	−178.9 (2)	C2B—C1B—C8B—C7B	−38.0 (3)
O15A—C6A—C7A—C8A	−64.4 (3)	C11B—C1B—C8B—C7B	−161.8 (2)
C5A—C6A—C7A—C8A	58.5 (3)	C2B—C1B—C8B—C9B	88.4 (2)
C6A—C7A—C8A—C9A	168.1 (2)	C11B—C1B—C8B—C9B	−35.4 (2)
C6A—C7A—C8A—C1A	−68.6 (3)	C7B—C8B—C9B—C10B	148.3 (3)
C2A—C1A—C8A—C7A	−36.9 (3)	C1B—C8B—C9B—C10B	16.6 (3)
C11A—C1A—C8A—C7A	−161.0 (2)	C8B—C9B—C10B—C11B	9.7 (3)
C2A—C1A—C8A—C9A	89.4 (3)	C9B—C10B—C11B—C19B	−162.4 (3)
C11A—C1A—C8A—C9A	−34.6 (3)	C9B—C10B—C11B—C1B	−32.5 (3)
C7A—C8A—C9A—C10A	146.3 (3)	C2B—C1B—C11B—C19B	44.1 (3)
C1A—C8A—C9A—C10A	14.6 (4)	C8B—C1B—C11B—C19B	170.1 (3)
C8A—C9A—C10A—C11A	12.2 (4)	C2B—C1B—C11B—C10B	−84.2 (3)
C9A—C10A—C11A—C19A	−164.3 (3)	C8B—C1B—C11B—C10B	41.7 (3)
C9A—C10A—C11A—C1A	−34.3 (3)	O18B—C6B—O15B—C16B	2.7 (4)
C2A—C1A—C11A—C19A	45.0 (3)	C7B—C6B—O15B—C16B	−113.5 (3)
C8A—C1A—C11A—C19A	171.2 (3)	C5B—C6B—O15B—C16B	119.1 (3)
C2A—C1A—C11A—C10A	−83.7 (3)	C6B—O15B—C16B—C17C	−21.3 (6)
C8A—C1A—C11A—C10A	42.4 (3)	C6B—O15B—C16B—C17B	13.0 (6)
O18A—C6A—O15A—C16A	19.0 (3)	O15B—C16B—C17B—O18B	−24.9 (8)
C7A—C6A—O15A—C16A	−98.0 (3)	C17C—C16B—C17B—O18B	69.6 (8)
C5A—C6A—O15A—C16A	134.4 (3)	O15B—C16B—C17C—O18B	31.7 (8)
C6A—O15A—C16A—C17A	−9.9 (5)	C17B—C16B—C17C—O18B	−62.8 (7)
O15A—C16A—C17A—O18A	−3.4 (6)	C16B—C17B—O18B—C17C	−63.9 (9)
C16A—C17A—O18A—C6A	15.6 (6)	C16B—C17B—O18B—C6B	27.6 (8)
O15A—C6A—O18A—C17A	−21.5 (4)	C16B—C17C—O18B—C17B	70.7 (9)
C7A—C6A—O18A—C17A	96.8 (4)	C16B—C17C—O18B—C6B	−30.6 (7)
C5A—C6A—O18A—C17A	−136.2 (4)	O15B—C6B—O18B—C17B	−20.3 (6)
C8B—C1B—C2B—O12B	−31.2 (3)	C7B—C6B—O18B—C17B	97.2 (6)
C11B—C1B—C2B—O12B	85.4 (2)	C5B—C6B—O18B—C17B	−136.0 (6)
C8B—C1B—C2B—C3B	95.9 (2)	O15B—C6B—O18B—C17C	17.9 (5)
C11B—C1B—C2B—C3B	−147.4 (2)	C7B—C6B—O18B—C17C	135.4 (5)
O12B—C2B—C3B—C13B	−171.6 (2)	C5B—C6B—O18B—C17C	−97.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12A—H12A···O15B^i	0.79 (4)	2.25 (4)	2.937 (3)	146 (4)
O12B—H12B···O15A^ii	0.82 (4)	2.19 (4)	2.912 (3)	148 (3)

Symmetry codes: (i) x−1, y, z; (ii) x, y, z−1.