(Z,2R,3R,4aR,7R,12aS)-2,3,7,8,12,12a-Hexahydro-2,3-dimethoxy-2,3,7-trimethyl-4aH-[1,4]dioxino[2,3-c]oxecin-5(11H)-one: a commensurate occupationally modulated structure revealing a condition for diffraction symmetry enhancement for non-parent reflections

(Z,2R,3R,4aR,7R,12aS)-2,3,7,8,12,12a-Hexahydro-2,3-dimethoxy-2,3,7-trimethyl-4aH-[1,4]dioxino[2,3-c]oxecin-5(11H)-one (C₁₆H₂₆O₆) crystallizes in the space group P3₁ and approximates the conditions necessary for diffraction symmetry enhancement without twinning for the h − k ≠ 3N reflections. The structure may be described as an occupancy modulation of a 1:1 disordered P3₁21 parent structure with Z = 3 that would only contribute to the h − k = 3N reflections. The crystal studied was a 0.717 (2):0.283 twin, but also had a stacking fault that on average caused the (1 − p_j):p_j population ratio for the alternative orientations of ordered columns along the three non-equivalent screw axes (j = 1, 2 or 3) of P3₁ to be describable by p₁ = 0.068 (3), p₂ = p₃ = 0.960 (3). The effect of these stacking faults could be simulated using global parameters that modify an ordered prototype structure. The structure reveals that the ten-membered lactone ring incorporates a Z-configured double bond and that the methoxy-substituted stereogenic centers created during a trans-diol protection step each possess the R-configuration.

S1. Comment

The crystal is twinned. The structure could be solved by direct methods using the raw data and assuming no twinning, but would not refine below 10%. The constrained least squares refinement program RAELS2000 can account for twinning, pseudo-symmetry and stacking faults and was ideal for refining this structure.

In the crystallographic asymmetric unit there are three C₁₆H₂₆O₆ molecules which are chemically identical and pseudo-symmetrically related. The crystal was a 0.716 (2): 0.284 twin and also had a stacking fault so that reflections with h − k ≠ 3 N had F_calc scaled by 0.912 (3) compared to reflections with h − k = 3 N. Also 0.011 (1) of the structure is a disorder created by the same pseudo symmetry operator as the observed twin rule that relates the hkl and −k-h-l reflections. Full details of the refinement procedure are given in the accompanying report and in _refine_special_details of the crystallographic information file (CIF).

There were no outstanding features in the final difference electron density map.

S2. Experimental

The compound was prepared by DTL and recrystallized from 2-propanol/dichloromethane. The sample ID is DTLRCMA.

S3. Refinement

Hydrogen atoms coordinates were refined with constraints and given atomic displacement parameters determined by the atoms to which they are attached.

Computing details

Data collection: COLLECT (Nonius BV, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: DENZO and Scalepak (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79); program(s) used to refine structure: RAELS2000 (Rae 2000); molecular graphics: ORTEP-II (Johnson 1976) in TEXSAN (MSC, 1992-1997); software used to prepare material for publication: maXus(Mackay et al., 1999).

Figures

(mgb045_rae)

Crystal data

C16H26O6	Dx = 1.268 Mg m^−3
Mr = 314.38	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 84318 reflections
a = 18.6850 (2) Å	θ = 2.6–27.5°
c = 12.2539 (1) Å	µ = 0.10 mm^−1
V = 3705.02 (6) Å^3	T = 200 K
Z = 9	Prism, colourless
F(000) = 1530	0.47 × 0.32 × 0.28 mm

Data collection

Enraf Nonius Kappa CCD diffractometer	5629 independent reflections
Radiation source: fine-focus sealed tube	5022 reflections with I > 3.00 σ(I)
Graphite monochromator	Rint = 0.055
ϕ and ω scans with CCD	θmax = 27.5°, θmin = 2.7°
Absorption correction: integration via Gaussian method (Coppens, 1970) implemented in maXus (2000)	h = −24→24
Tmin = 0.963, Tmax = 0.985	k = −24→24
98252 measured reflections	l = −15→15

Refinement

Refinement on F	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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.048	H-atom parameters constrained
S = 1.28	Weighting scheme based on measured s.u.'s w = 1 / ( σ^2(Fo^2) + 0.0009 × Fo^2)
5022 reflections	(Δ/σ)max = 0.1
707 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3
0 constraints	Absolute structure: The enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure.

Special details

Refinement. MGB045 C16H26O6

a = b 18.6850 (2), c 12.2359 (1) Å, a 90, b 90, g 120 °. Space group P31 Z = 9

The constrained least squares refinement program RAELS2000 was used for refinement. The crystal studied was a 0.716 (2): 0.284 twin and also had a stacking fault so that reflections with h − k ≠ 3 N had Fcalc scaled by 0.912 (3) compared to reflections with h − k = 3 N. Also 0.011 (1) of the structure is a disorder created by the same pseudo symmetry operator as the observed twin rule that relates the hkl and −k-h-l reflections.

The structure contains three columns of 31 symmetry in the unit cell along 1/3,2/3,z; 1,1, z; and 2/3,1/3,z related by the pseudo symmetry operation 5/3 − y,4/3 − x,1 − z. The structure can be described as an occupancy ordering of a 1:1 disordered parent structure in space group P3121 with one third the cell volume and Z = 3. A 2 fold axis is the disordering operation and the origin can be chosen so that this 2 fold axis passes through it. Ordering allows each column to take up one of the two orientations related by this two fold axis perpendicular to c. The resulting structure contains a pseudo two fold screw axis 5/3 − y, 4/3 − x, 1 − z relating the three moleculues in the asymmetric unit of P31. The atoms O17, O117, O217 lie approximately on this screw axis. The ordered structure has two columns in one orientation and the other column is in the alternative orientation. This creates diffraction symmetry enhancement without twinning for the h − k ≠ 3 N reflections should the pseudo 2 fold screw axis operations hold exactly. The 2: 1 ratio of columns in different orientations must be compromised in a twin disorder mechanism to explain the final refinement model which scaled the h- k ≠ 3 N reflections relative to the h- k = 3 N reflections and applied a twin-disorder rule relating the hkl and −k-h-l reflection intensities.

Various constraints were used in refinement to reduce the number of variables and allow the H atoms to be refined. Pseudo screw axis related O—Me and C—Me atom groups were constrained to have identical refineable geometries of exact local 3 m symmetry using refinable local orthonormal axial systems and refineable local orthoonormal axial systems (Rae, 1975). Non pseudo equivalent O—C and C—C distances were allowed to be independent. However only two sets of local coordinates were used for the methyl H atoms, one set for all methyls attached to an O atom, the other for the methyls attached to a C atom. All non H atoms had independent anisotropic atom displacement parameters and the H atoms were constrained to have the same parameters as the atom to which they were attached. Three sets of methyl H atoms, those attached to O20, O120 and O220 were allowed an extra common libration about the relevant C—H bond that was common to all 3 sets. These constraints allowed an essentially anisotropic refinement of all atoms using 707 variables for a reflection set of 5022 independent reflections with I >3σ(I) obtained after merging assuming P-3 diffraction symmetry.

The twinning reduced the difference between twin related reflection intensities by a factor of 0.432 compared to an untwinned crystal. The R_merge for P-3 was 0.055 compared to 0.114 for P-31m diffraction symmetry. Data sets were collected for three different crystals and the crystal chosen for refinement was the one that had the best R_merge for P-3 but the worst for P-31m. An initial structure solution was obtained by direct methods using SIR97 and space group P31. The handedness of the molecule was known and P31 rather than the inverted structure in P32 is appropriate.

Effect on Intensities of stacking faults

The structure can be described as three pseudosymmetry related columns as described above. The columns at 1/3,2/3,z amd 2/3,1/3,z are related by the translation 1/3(a − b).

If we say F1(h) is the stucture factor for a column at the origin and if we choose the origin along c so that a 2 fold rotation through the origin creates the alternative orientation for each column, then assuming only an occupancy modulation of a 1:1 disordered parent structure

F(h) = [(1-p1) + ω (1-p2) + ω* (1-p3)]F1(h) + [p1 + ω p2 + ω* p3]F1(2 h)

where ω = exp(2πi(h-k)/3) and (1-pj): pj gives the population ratio for the alternative orientations of a column. The perfectly ordered structure corresponding to our listed coordinates has p1, p2, p3 = 0,1,1. Values for p1, p2, p3 of 1,0,1 and 1,1,0 correspond to different origin choices. Structures related by a 2 fold rotation through the origin are obtained by swapping the values of (1-pj) and pj. Translational stacking faults of layers would preserve the value of p1 + p2 + p3.

When h − k ≠ 3 N F(h) = [p1 + ω p2 + ω* p3][F1(2 h) - F1(h)]

and F(2 h) = [p1 + ω* p2 + ω p3][F1(h) - F1(2 h)] so that

I(h) = I(2 h) = [p12 + p22 + p32 - p1p2 - p2p3 - p3p1]|F1(h) - F1(2 h)|2.

For a perfectly ordered structure I(h) = I(2 h) = |F1(h) - F1(2 h)|2 and F(h) = - F(2 h). It is possible to have diffraction symmetry enhancement and scaling without the need for twinning to describe these reflections should the pseudo symmetry operations hold exactly.

When h − k = 3 N F(h) = 3/2[F1(h) + F1(2 h)] + [p1 + p2 + p3 − 3/2][F1(2 h) - F1(h)]

and F(2 h) = 3/2[F1(h) + F1(2 h)] - [p1 + p2 + p3 − 3/2][F1(2 h) - F1(h)]

so that [I(h) + I(2 h)]/2 = 9/4|F1(h) + F1(2 h)|2 + [p1 + p2 + p3 − 3/2]2 |F1(2 h) - F1(h)|2

and [I(h) - I(2 h)]/2 = 6 [p1 + p2 + p3 − 3/2] [|F1(2 h)|2 - |F1(h)|2].

If we preserve the value of p1 + p2 + p3 as 2 then

F(h) = [F1(h) + 2 F1(2 h)] and F(2 h) = [2 F1(h) + F1(2 h)]

so that [I(h) + I(2 h)]/2 = 9/4 |F1(h) + F1(2 h)|2 + 1/4 |F1(2 h) - F1(h)|2

and I(h) - I(2 h)]/2 = ± 3 [|F1(2 h)|2 - |F1(h)|2].

Our first model refined a twin ratio (1 − q): q where q = 0.283 (2) and a separate scale for h − k ≠ 3 N reflections. The twinning to multiply I(h) - I(2 h)]/2 by 1 − 2q = 0.434 (4) rather than 1.0 implies a two fold screw axis perpendicular to c must be involved in creating a truly twin- disorder structure. The scaling of h − k ≠ 3 N reflection amplitudes by 0.896 (3) would imply the value of [p12 + p22 + p32 - p1p2 - p2p3 - p3p1] = 0.803 (6), i.e 0.8962, when averaged over twin related mosaic blocks. This is capable of many solutions and offers no further information.

This refinement assumed that p1 + p2 + p3 = 2 and makes 1/4|F1(2 h) - F1(h)]|2 to be just 10% of [I(h) + I(2 h)]/2 on average. Any disorder will probably make [p1 + p2 + p3 − 3/2]2 tend to zero. This model is refineable and was achieved using the model

I(h) = (1 − q)[(1-p) F(h) + p F(2 h)]2 + q[(1-p) F(2 h) + p F(h)]2,

where disorder parameter p and the twin parameter q are refinable using RAELS2000.

If we no longer use two scales we imply that there are no translational stacking faults. Such a refinement improves the data fit for h − k = 3 N but makes it worse for h − k 3 N and suggested that both types of stacking faults are present and two scales should still be used. This final model refined successfully and gave the results described in the summary at the beginning of this report.

References

(1) RAELS2000, A·D. Rae (2000) Australian National University, Canberra, Australia.

(2) Rae, A·D. (1975) Acta Cryst. A31, 560–570, 570–574.

Table 1. Refinement Statistics.

Class** Number R(F) R(F2) wR Gof

1 1702 0.035 0.059 0.047 1.346

2 3320 0.040 0.073 0.048 1.264

1–2 5022 0.038 0.065 0.048 1.292

3 607 0.210 0.386 0.248 1.072

1–3 5629 0.043 0.066 0.050 1.281

An uncorrelated 3% error in |F(h)| was included along with counting statistic error for evaluating weights w = 1/(σ(F)2 + (0.03 F)2). Refinement was on F.

Index 1 Reflections with I > 3σ(I) and h − k = 3 N

Index 2 Reflections with I > 3σ(I) and h − k ≠ 3 N

Index 3 Reflections with I < 3σ(I).

The refinement used 707 variables for 66 non H atoms and 78 H atoms. Residual electron density, minimum −0.230 e Å-3, maximum 0.255 e Å-3.

In the final full matrix refinement cycle no parameter shifts were greater than 0.1 σ.

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

	x	y	z	Uiso*/Ueq
C1	0.5333 (2)	0.7476 (2)	0.7351 (3)	0.030 (1)
C2	0.5201 (2)	0.7819 (2)	0.6298 (3)	0.028 (1)
C3	0.4439 (2)	0.7172 (2)	0.5690 (3)	0.034 (1)
C4	0.4518 (3)	0.6446 (2)	0.5272 (3)	0.040 (1)
C5	0.4288 (2)	0.5755 (2)	0.6120 (4)	0.043 (1)
C6	0.4890 (2)	0.5445 (2)	0.6155 (3)	0.040 (1)
C7	0.5372 (3)	0.5514 (2)	0.6976 (3)	0.042 (1)
C8	0.5417 (3)	0.5924 (2)	0.8055 (3)	0.039 (1)
C9	0.6065 (2)	0.6835 (2)	0.8095 (3)	0.035 (1)
O10	0.5922 (1)	0.7273 (1)	0.7201 (2)	0.032 (1)
C11	0.6940 (2)	0.7007 (2)	0.7925 (2)	0.046 (1)
O12	0.4962 (2)	0.7379 (2)	0.8193 (2)	0.041 (1)
O13	0.5108 (2)	0.8510 (1)	0.6597 (2)	0.032 (1)
C14	0.5000 (2)	0.8912 (2)	0.5670 (3)	0.032 (1)
C15	0.4268 (2)	0.8276 (2)	0.4959 (2)	0.036 (1)
O16	0.4357 (2)	0.7580 (2)	0.4735 (2)	0.036 (1)
O17	0.5705 (2)	0.9219 (2)	0.4981 (2)	0.037 (1)
C18	0.6455 (2)	0.9896 (2)	0.5388 (2)	0.046 (1)
C19	0.4875 (2)	0.9593 (2)	0.6139 (2)	0.042 (1)
O20	0.3561 (2)	0.8059 (2)	0.5607 (2)	0.044 (1)
C21	0.2795 (2)	0.7425 (2)	0.5179 (2)	0.065 (1)
C22	0.4232 (3)	0.8616 (2)	0.3849 (2)	0.047 (1)
C101	0.9251 (2)	0.8018 (2)	0.2630 (3)	0.025 (1)
C102	0.8876 (2)	0.8142 (2)	0.3666 (3)	0.026 (1)
C103	0.9500 (2)	0.8900 (2)	0.4312 (3)	0.028 (1)
C104	1.0222 (2)	0.8817 (3)	0.4757 (3)	0.037 (1)
C105	1.0937 (2)	0.9088 (2)	0.3926 (3)	0.037 (1)
C106	1.1278 (2)	0.8510 (3)	0.3898 (3)	0.040 (1)
C107	1.1236 (2)	0.8033 (3)	0.3059 (3)	0.038 (1)
C108	1.0837 (2)	0.8000 (3)	0.1978 (3)	0.037 (1)
C109	0.9935 (2)	0.7323 (2)	0.1921 (3)	0.032 (1)
O110	0.9477 (1)	0.7459 (1)	0.2797 (2)	0.026 (1)
C111	0.9791 (2)	0.6458 (2)	0.2084 (2)	0.044 (1)
O112	0.9339 (2)	0.8394 (2)	0.1797 (2)	0.036 (1)
O113	0.8187 (1)	0.8225 (1)	0.3357 (2)	0.026 (1)
C114	0.7765 (2)	0.8323 (2)	0.4267 (3)	0.031 (1)
C115	0.8387 (2)	0.9067 (2)	0.4980 (2)	0.033 (1)
O116	0.9079 (2)	0.8980 (2)	0.5235 (2)	0.034 (1)
O117	0.7472 (2)	0.7641 (2)	0.4979 (2)	0.039 (1)
C118	0.6873 (2)	0.6869 (2)	0.4517 (2)	0.053 (1)
C119	0.7088 (2)	0.8449 (3)	0.3785 (2)	0.041 (1)
O120	0.8618 (2)	0.9763 (1)	0.4304 (2)	0.040 (1)
C121	0.9230 (3)	1.0541 (2)	0.4726 (2)	0.063 (1)
C122	0.8034 (2)	0.9118 (3)	0.6073 (2)	0.046 (1)
C201	0.8612 (2)	0.3993 (2)	0.7394 (3)	0.029 (1)
C202	0.8528 (2)	0.4383 (2)	0.6357 (3)	0.028 (1)
C203	0.7752 (2)	0.3781 (2)	0.5720 (3)	0.031 (1)
C204	0.7781 (2)	0.3038 (2)	0.5284 (3)	0.038 (1)
C205	0.7447 (2)	0.2312 (2)	0.6091 (3)	0.038 (1)
C206	0.7975 (2)	0.1912 (2)	0.6142 (3)	0.037 (1)
C207	0.8427 (2)	0.1922 (2)	0.6981 (3)	0.036 (1)
C208	0.8485 (2)	0.2331 (2)	0.8054 (3)	0.037 (1)
C209	0.9209 (2)	0.3215 (2)	0.8123 (3)	0.032 (1)
O210	0.9150 (1)	0.3718 (1)	0.7240 (2)	0.030 (1)
C211	1.0038 (2)	0.3268 (2)	0.7968 (2)	0.043 (1)
O212	0.8242 (2)	0.3906 (2)	0.8230 (2)	0.041 (1)
O213	0.8483 (2)	0.5093 (1)	0.6679 (2)	0.032 (1)
C214	0.8431 (2)	0.5539 (2)	0.5760 (3)	0.035 (1)
C215	0.7677 (2)	0.4951 (2)	0.5051 (2)	0.037 (1)
O216	0.7706 (2)	0.4227 (2)	0.4788 (2)	0.035 (1)
O217	0.9128 (2)	0.5789 (2)	0.5067 (2)	0.043 (1)
C218	0.9918 (2)	0.6333 (2)	0.5535 (2)	0.056 (1)
C219	0.8382 (3)	0.6261 (2)	0.6241 (2)	0.047 (1)
O220	0.6983 (2)	0.4764 (2)	0.5704 (2)	0.044 (1)
C221	0.6198 (2)	0.4183 (2)	0.5263 (2)	0.062 (1)
C222	0.7663 (3)	0.5326 (2)	0.3958 (2)	0.050 (1)
H2	0.572 (3)	0.808 (3)	0.586 (4)	0.039 (1)
H3	0.386 (3)	0.699 (3)	0.621 (4)	0.035 (1)
H4A	0.425 (3)	0.626 (3)	0.460 (4)	0.032 (1)
H4B	0.509 (3)	0.671 (3)	0.497 (4)	0.032 (1)
H5A	0.430 (3)	0.596 (3)	0.690 (5)	0.046 (1)
H5B	0.362 (3)	0.527 (3)	0.591 (4)	0.046 (1)
H6	0.486 (3)	0.520 (4)	0.544 (4)	0.041 (1)
H7	0.567 (3)	0.519 (3)	0.682 (4)	0.032 (1)
H8A	0.486 (3)	0.589 (3)	0.827 (4)	0.032 (1)
H8B	0.552 (3)	0.569 (3)	0.873 (4)	0.032 (1)
H9	0.601 (3)	0.706 (3)	0.878 (4)	0.036 (1)
H11A	0.7068 (9)	0.6693 (16)	0.8451 (17)	0.036 (1)
H11B	0.7331 (6)	0.7596 (7)	0.802 (3)	0.036 (1)
H11C	0.7002 (8)	0.6846 (18)	0.7187 (11)	0.036 (1)
H18A	0.6916 (8)	0.9954 (13)	0.4938 (17)	0.042 (1)
H18B	0.6528 (11)	0.9781 (11)	0.6149 (12)	0.042 (1)
H18C	0.6415 (10)	1.0400 (8)	0.535 (2)	0.042 (1)
H19A	0.488 (2)	0.9952 (13)	0.5555 (8)	0.044 (1)
H19B	0.5317 (12)	0.9926 (13)	0.666 (2)	0.044 (1)
H19C	0.4345 (11)	0.9354 (6)	0.652 (2)	0.044 (1)
H21A	0.2361 (8)	0.729 (2)	0.5724 (17)	0.069 (6)
H21B	0.2846 (11)	0.6937 (11)	0.503 (3)	0.066 (2)
H21C	0.2672 (15)	0.7628 (12)	0.451 (2)	0.067 (2)
H22A	0.417 (2)	0.9099 (15)	0.3934 (8)	0.047 (1)
H22B	0.3766 (14)	0.8196 (10)	0.3429 (13)	0.047 (1)
H22C	0.4743 (11)	0.878 (2)	0.3445 (14)	0.047 (1)
H102	0.872 (3)	0.768 (3)	0.409 (4)	0.037 (1)
H103	0.968 (3)	0.937 (3)	0.383 (4)	0.032 (1)
H104A	1.048 (3)	0.922 (3)	0.538 (4)	0.026 (1)
H104B	1.006 (3)	0.821 (3)	0.496 (4)	0.026 (1)
H105A	1.076 (3)	0.917 (3)	0.318 (5)	0.044 (1)
H105B	1.129 (4)	0.955 (4)	0.411 (4)	0.044 (1)
H106	1.155 (3)	0.849 (3)	0.458 (4)	0.036 (1)
H107	1.149 (3)	0.762 (3)	0.302 (4)	0.026 (1)
H108A	1.088 (3)	0.856 (3)	0.184 (4)	0.031 (1)
H108B	1.115 (3)	0.791 (3)	0.143 (4)	0.031 (1)
H109	0.965 (3)	0.736 (3)	0.121 (4)	0.033 (1)
H111A	1.0110 (15)	0.6343 (8)	0.1552 (17)	0.034 (1)
H111B	0.9204 (6)	0.6053 (6)	0.199 (2)	0.034 (1)
H111C	0.9961 (17)	0.6401 (8)	0.2819 (11)	0.034 (1)
H118A	0.6750 (15)	0.6429 (7)	0.5049 (13)	0.041 (1)
H118B	0.7102 (10)	0.6775 (11)	0.3846 (15)	0.041 (1)
H118C	0.6371 (9)	0.6893 (10)	0.435 (2)	0.041 (1)
H119A	0.6745 (13)	0.848 (2)	0.4367 (8)	0.040 (1)
H119B	0.6738 (13)	0.7989 (11)	0.330 (2)	0.040 (1)
H119C	0.7331 (6)	0.8963 (11)	0.337 (2)	0.040 (1)
H121A	0.940 (2)	1.0956 (9)	0.4143 (13)	0.066 (6)
H121B	0.9703 (13)	1.0493 (10)	0.498 (3)	0.064 (2)
H121C	0.8991 (11)	1.0691 (14)	0.534 (2)	0.065 (2)
H122A	0.7569 (15)	0.921 (2)	0.5964 (8)	0.046 (1)
H122B	0.8457 (9)	0.9573 (15)	0.6505 (14)	0.046 (1)
H122C	0.784 (2)	0.8602 (10)	0.6477 (14)	0.046 (1)
H202	0.901 (3)	0.460 (3)	0.591 (4)	0.037 (1)
H203	0.728 (3)	0.365 (3)	0.620 (4)	0.032 (1)
H204A	0.754 (3)	0.290 (3)	0.457 (4)	0.030 (1)
H204B	0.838 (3)	0.320 (3)	0.513 (4)	0.030 (1)
H205A	0.745 (3)	0.252 (3)	0.692 (4)	0.043 (1)
H205B	0.684 (3)	0.193 (3)	0.593 (4)	0.043 (1)
H206	0.793 (3)	0.156 (3)	0.549 (4)	0.041 (1)
H207	0.888 (3)	0.168 (3)	0.681 (3)	0.032 (1)
H208A	0.795 (3)	0.237 (3)	0.824 (4)	0.035 (1)
H208B	0.861 (3)	0.208 (3)	0.872 (4)	0.035 (1)
H209	0.920 (3)	0.351 (3)	0.883 (4)	0.037 (1)
H211A	1.0081 (9)	0.2871 (14)	0.8443 (19)	0.035 (1)
H211B	1.0485 (6)	0.3823 (8)	0.815 (2)	0.035 (1)
H211C	1.0101 (10)	0.3145 (19)	0.7210 (9)	0.035 (1)
H218A	1.0347 (7)	0.6337 (16)	0.5066 (16)	0.047 (1)
H218B	0.9940 (10)	0.6130 (13)	0.6266 (13)	0.047 (1)
H218C	0.9990 (11)	0.6889 (8)	0.558 (2)	0.047 (1)
H219A	0.834 (2)	0.6598 (13)	0.5657 (8)	0.044 (1)
H219B	0.8874 (11)	0.6607 (12)	0.668 (2)	0.044 (1)
H219C	0.7894 (12)	0.6060 (6)	0.671 (2)	0.044 (1)
H221A	0.5780 (8)	0.402 (2)	0.5840 (13)	0.065 (6)
H221B	0.6224 (11)	0.3701 (13)	0.500 (3)	0.063 (2)
H221C	0.6070 (13)	0.4447 (11)	0.466 (2)	0.063 (2)
H222A	0.762 (2)	0.5823 (14)	0.4069 (8)	0.050 (1)
H222B	0.7188 (14)	0.4929 (10)	0.3528 (14)	0.050 (1)
H222C	0.8169 (12)	0.548 (2)	0.3552 (14)	0.050 (1)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.035 (2)	0.024 (2)	0.033 (2)	0.016 (1)	0.000 (1)	−0.001 (1)
C2	0.034 (2)	0.025 (2)	0.030 (2)	0.018 (1)	−0.001 (1)	−0.003 (1)
C3	0.038 (2)	0.033 (2)	0.032 (2)	0.018 (2)	−0.002 (1)	0.006 (1)
C4	0.052 (2)	0.031 (2)	0.038 (2)	0.021 (2)	−0.006 (2)	−0.001 (2)
C5	0.041 (2)	0.028 (2)	0.054 (2)	0.013 (2)	−0.008 (2)	0.002 (2)
C6	0.048 (2)	0.024 (2)	0.045 (2)	0.015 (2)	−0.003 (2)	−0.003 (2)
C7	0.056 (2)	0.030 (2)	0.043 (2)	0.023 (2)	−0.003 (2)	−0.001 (2)
C8	0.054 (2)	0.035 (2)	0.032 (2)	0.026 (2)	−0.001 (2)	0.003 (1)
C9	0.050 (2)	0.036 (2)	0.026 (2)	0.027 (2)	−0.009 (2)	0.001 (1)
O10	0.036 (1)	0.033 (1)	0.031 (1)	0.020 (1)	−0.003 (1)	0.002 (1)
C11	0.050 (2)	0.047 (2)	0.047 (2)	0.029 (2)	−0.007 (2)	0.003 (2)
O12	0.053 (2)	0.053 (2)	0.032 (1)	0.036 (1)	0.007 (1)	0.006 (1)
O13	0.043 (1)	0.030 (1)	0.031 (1)	0.023 (1)	0.000 (1)	0.003 (1)
C14	0.038 (2)	0.033 (2)	0.031 (2)	0.021 (2)	0.000 (1)	0.004 (1)
C15	0.042 (2)	0.039 (2)	0.034 (2)	0.025 (2)	−0.003 (1)	0.004 (1)
O16	0.044 (1)	0.035 (1)	0.032 (1)	0.022 (1)	−0.005 (1)	0.001 (1)
O17	0.036 (1)	0.033 (1)	0.040 (1)	0.015 (1)	0.004 (1)	0.008 (1)
C18	0.043 (2)	0.043 (2)	0.051 (2)	0.021 (2)	−0.002 (2)	−0.002 (2)
C19	0.059 (2)	0.042 (2)	0.041 (2)	0.038 (2)	0.002 (2)	0.006 (2)
O20	0.036 (1)	0.052 (2)	0.046 (2)	0.023 (1)	−0.002 (1)	0.005 (1)
C21	0.037 (2)	0.071 (3)	0.079 (3)	0.021 (2)	−0.009 (2)	0.013 (3)
C22	0.056 (2)	0.051 (2)	0.041 (2)	0.032 (2)	−0.007 (2)	0.005 (2)
C101	0.027 (2)	0.028 (2)	0.021 (2)	0.014 (1)	−0.002 (1)	−0.004 (1)
C102	0.026 (2)	0.029 (2)	0.024 (2)	0.013 (1)	0.005 (1)	0.001 (1)
C103	0.030 (2)	0.031 (2)	0.024 (2)	0.016 (1)	−0.003 (1)	−0.003 (1)
C104	0.033 (2)	0.051 (2)	0.029 (2)	0.022 (2)	−0.006 (1)	−0.010 (2)
C105	0.028 (2)	0.035 (2)	0.040 (2)	0.009 (2)	−0.003 (2)	−0.008 (2)
C106	0.028 (2)	0.051 (2)	0.038 (2)	0.019 (2)	−0.004 (2)	−0.003 (2)
C107	0.031 (2)	0.047 (2)	0.038 (2)	0.021 (2)	0.000 (1)	0.002 (2)
C108	0.032 (2)	0.053 (2)	0.030 (2)	0.025 (2)	0.004 (1)	0.000 (2)
C109	0.036 (2)	0.040 (2)	0.028 (2)	0.025 (2)	0.002 (1)	−0.002 (1)
O110	0.026 (1)	0.029 (1)	0.026 (1)	0.016 (1)	0.001 (1)	0.000 (1)
C111	0.057 (2)	0.040 (2)	0.049 (2)	0.034 (2)	−0.001 (2)	−0.008 (2)
O112	0.046 (1)	0.047 (2)	0.024 (1)	0.031 (1)	0.004 (1)	0.006 (1)
O113	0.025 (1)	0.034 (1)	0.022 (1)	0.016 (1)	0.000 (1)	−0.002 (1)
C114	0.031 (2)	0.040 (2)	0.027 (2)	0.020 (2)	0.008 (1)	0.001 (1)
C115	0.042 (2)	0.040 (2)	0.024 (2)	0.027 (2)	0.004 (1)	−0.002 (1)
O116	0.041 (1)	0.041 (1)	0.025 (1)	0.024 (1)	−0.001 (1)	−0.008 (1)
O117	0.044 (2)	0.037 (1)	0.032 (1)	0.016 (1)	0.011 (1)	0.008 (1)
C118	0.037 (2)	0.038 (2)	0.071 (3)	0.008 (2)	0.004 (2)	0.000 (2)
C119	0.037 (2)	0.055 (2)	0.043 (2)	0.031 (2)	0.004 (2)	−0.001 (2)
O120	0.053 (2)	0.034 (1)	0.038 (1)	0.025 (1)	0.002 (1)	0.002 (1)
C121	0.088 (4)	0.036 (2)	0.060 (3)	0.027 (2)	0.006 (3)	−0.009 (2)
C122	0.061 (3)	0.067 (3)	0.025 (2)	0.043 (2)	0.007 (2)	−0.005 (2)
C201	0.033 (2)	0.023 (2)	0.032 (2)	0.015 (1)	0.000 (1)	0.002 (1)
C202	0.034 (2)	0.028 (2)	0.028 (2)	0.019 (1)	−0.001 (1)	0.000 (1)
C203	0.033 (2)	0.035 (2)	0.027 (2)	0.018 (2)	−0.005 (1)	0.001 (1)
C204	0.044 (2)	0.035 (2)	0.034 (2)	0.020 (2)	−0.001 (2)	−0.002 (1)
C205	0.034 (2)	0.029 (2)	0.048 (2)	0.013 (2)	−0.006 (2)	0.000 (2)
C206	0.041 (2)	0.027 (2)	0.036 (2)	0.013 (2)	0.000 (1)	−0.004 (1)
C207	0.045 (2)	0.027 (2)	0.035 (2)	0.018 (2)	0.003 (2)	0.005 (1)
C208	0.048 (2)	0.033 (2)	0.032 (2)	0.023 (2)	0.006 (2)	0.006 (1)
C209	0.042 (2)	0.031 (2)	0.030 (2)	0.024 (2)	−0.006 (1)	0.003 (1)
O210	0.032 (1)	0.032 (1)	0.032 (1)	0.020 (1)	0.000 (1)	0.004 (1)
C211	0.047 (2)	0.047 (2)	0.043 (2)	0.029 (2)	−0.006 (2)	0.004 (2)
O212	0.059 (2)	0.050 (2)	0.030 (1)	0.038 (1)	0.010 (1)	0.007 (1)
O213	0.042 (1)	0.032 (1)	0.028 (1)	0.023 (1)	0.000 (1)	0.003 (1)
C214	0.046 (2)	0.034 (2)	0.030 (2)	0.024 (2)	0.007 (1)	0.010 (1)
C215	0.048 (2)	0.046 (2)	0.029 (2)	0.033 (2)	0.003 (1)	0.006 (1)
O216	0.045 (1)	0.042 (1)	0.026 (1)	0.028 (1)	−0.004 (1)	0.001 (1)
O217	0.049 (2)	0.044 (2)	0.035 (1)	0.022 (1)	0.007 (1)	0.011 (1)
C218	0.047 (2)	0.054 (3)	0.059 (3)	0.019 (2)	0.005 (2)	0.011 (2)
C219	0.075 (3)	0.044 (2)	0.038 (2)	0.042 (2)	−0.001 (2)	0.008 (2)
O220	0.040 (1)	0.060 (2)	0.040 (1)	0.031 (1)	−0.001 (1)	0.002 (1)
C221	0.044 (2)	0.074 (3)	0.068 (3)	0.030 (2)	−0.005 (2)	0.001 (3)
C222	0.070 (3)	0.059 (3)	0.036 (2)	0.044 (2)	−0.006 (2)	0.004 (2)
H2	0.054 (2)	0.035 (2)	0.032 (2)	0.026 (2)	−0.001 (2)	0.003 (1)
H3	0.050 (2)	0.036 (2)	0.026 (2)	0.027 (2)	−0.009 (2)	0.001 (1)
H4A	0.036 (1)	0.033 (1)	0.031 (1)	0.020 (1)	−0.003 (1)	0.002 (1)
H4B	0.036 (1)	0.033 (1)	0.031 (1)	0.020 (1)	−0.003 (1)	0.002 (1)
H5A	0.050 (2)	0.047 (2)	0.047 (2)	0.029 (2)	−0.007 (2)	0.003 (2)
H5B	0.050 (2)	0.047 (2)	0.047 (2)	0.029 (2)	−0.007 (2)	0.003 (2)
H6	0.053 (2)	0.053 (2)	0.032 (1)	0.036 (1)	0.007 (1)	0.006 (1)
H7	0.043 (1)	0.030 (1)	0.031 (1)	0.023 (1)	0.000 (1)	0.003 (1)
H8A	0.038 (2)	0.033 (2)	0.031 (2)	0.021 (2)	0.000 (1)	0.004 (1)
H8B	0.038 (2)	0.033 (2)	0.031 (2)	0.021 (2)	0.000 (1)	0.004 (1)
H9	0.042 (2)	0.039 (2)	0.034 (2)	0.025 (2)	−0.003 (1)	0.004 (1)
H11A	0.044 (1)	0.035 (1)	0.032 (1)	0.022 (1)	−0.005 (1)	0.001 (1)
H11B	0.044 (1)	0.035 (1)	0.032 (1)	0.022 (1)	−0.005 (1)	0.001 (1)
H11C	0.044 (1)	0.035 (1)	0.032 (1)	0.022 (1)	−0.005 (1)	0.001 (1)
H18A	0.059 (2)	0.042 (2)	0.041 (2)	0.038 (2)	0.002 (2)	0.006 (2)
H18B	0.059 (2)	0.042 (2)	0.041 (2)	0.038 (2)	0.002 (2)	0.006 (2)
H18C	0.059 (2)	0.042 (2)	0.041 (2)	0.038 (2)	0.002 (2)	0.006 (2)
H19A	0.036 (1)	0.052 (2)	0.046 (2)	0.023 (1)	−0.002 (1)	0.005 (1)
H19B	0.036 (1)	0.052 (2)	0.046 (2)	0.023 (1)	−0.002 (1)	0.005 (1)
H19C	0.036 (1)	0.052 (2)	0.046 (2)	0.023 (1)	−0.002 (1)	0.005 (1)
H21A	0.041 (8)	0.077 (10)	0.083 (6)	0.026 (9)	−0.005 (7)	0.018 (8)
H21B	0.039 (3)	0.072 (3)	0.081 (5)	0.022 (3)	−0.011 (4)	0.012 (4)
H21C	0.042 (8)	0.076 (9)	0.079 (3)	0.025 (8)	−0.008 (2)	0.014 (3)
H22A	0.056 (2)	0.051 (2)	0.041 (2)	0.032 (2)	−0.007 (2)	0.005 (2)
H22B	0.056 (2)	0.051 (2)	0.041 (2)	0.032 (2)	−0.007 (2)	0.005 (2)
H22C	0.056 (2)	0.051 (2)	0.041 (2)	0.032 (2)	−0.007 (2)	0.005 (2)
H102	0.032 (2)	0.053 (2)	0.030 (2)	0.025 (2)	0.004 (1)	0.000 (2)
H103	0.036 (2)	0.040 (2)	0.028 (2)	0.025 (2)	0.002 (1)	−0.002 (1)
H104A	0.026 (1)	0.029 (1)	0.026 (1)	0.016 (1)	0.001 (1)	0.000 (1)
H104B	0.026 (1)	0.029 (1)	0.026 (1)	0.016 (1)	0.001 (1)	0.000 (1)
H105A	0.057 (2)	0.040 (2)	0.049 (2)	0.034 (2)	−0.001 (2)	−0.008 (2)
H105B	0.057 (2)	0.040 (2)	0.049 (2)	0.034 (2)	−0.001 (2)	−0.008 (2)
H106	0.046 (1)	0.047 (2)	0.024 (1)	0.031 (1)	0.004 (1)	0.006 (1)
H107	0.025 (1)	0.034 (1)	0.022 (1)	0.016 (1)	0.000 (1)	−0.002 (1)
H108A	0.031 (2)	0.040 (2)	0.027 (2)	0.020 (2)	0.008 (1)	0.001 (1)
H108B	0.031 (2)	0.040 (2)	0.027 (2)	0.020 (2)	0.008 (1)	0.001 (1)
H109	0.042 (2)	0.040 (2)	0.024 (2)	0.027 (2)	0.004 (1)	−0.002 (1)
H111A	0.041 (1)	0.041 (1)	0.025 (1)	0.024 (1)	−0.001 (1)	−0.008 (1)
H111B	0.041 (1)	0.041 (1)	0.025 (1)	0.024 (1)	−0.001 (1)	−0.008 (1)
H111C	0.041 (1)	0.041 (1)	0.025 (1)	0.024 (1)	−0.001 (1)	−0.008 (1)
H118A	0.037 (2)	0.055 (2)	0.043 (2)	0.031 (2)	0.004 (2)	−0.001 (2)
H118B	0.037 (2)	0.055 (2)	0.043 (2)	0.031 (2)	0.004 (2)	−0.001 (2)
H118C	0.037 (2)	0.055 (2)	0.043 (2)	0.031 (2)	0.004 (2)	−0.001 (2)
H119A	0.053 (2)	0.034 (1)	0.038 (1)	0.025 (1)	0.002 (1)	0.002 (1)
H119B	0.053 (2)	0.034 (1)	0.038 (1)	0.025 (1)	0.002 (1)	0.002 (1)
H119C	0.053 (2)	0.034 (1)	0.038 (1)	0.025 (1)	0.002 (1)	0.002 (1)
H121A	0.094 (11)	0.041 (8)	0.064 (7)	0.033 (9)	0.010 (8)	−0.005 (7)
H121B	0.089 (4)	0.038 (4)	0.062 (4)	0.029 (4)	0.004 (4)	−0.011 (4)
H121C	0.092 (8)	0.040 (7)	0.060 (3)	0.031 (7)	0.006 (3)	−0.009 (2)
H122A	0.061 (3)	0.067 (3)	0.025 (2)	0.043 (2)	0.007 (2)	−0.005 (2)
H122B	0.061 (3)	0.067 (3)	0.025 (2)	0.043 (2)	0.007 (2)	−0.005 (2)
H122C	0.061 (3)	0.067 (3)	0.025 (2)	0.043 (2)	0.007 (2)	−0.005 (2)
H202	0.048 (2)	0.033 (2)	0.032 (2)	0.023 (2)	0.006 (2)	0.006 (1)
H203	0.042 (2)	0.031 (2)	0.030 (2)	0.024 (2)	−0.006 (1)	0.003 (1)
H204A	0.032 (1)	0.032 (1)	0.032 (1)	0.020 (1)	0.000 (1)	0.004 (1)
H204B	0.032 (1)	0.032 (1)	0.032 (1)	0.020 (1)	0.000 (1)	0.004 (1)
H205A	0.047 (2)	0.047 (2)	0.043 (2)	0.029 (2)	−0.006 (2)	0.004 (2)
H205B	0.047 (2)	0.047 (2)	0.043 (2)	0.029 (2)	−0.006 (2)	0.004 (2)
H206	0.059 (2)	0.050 (2)	0.030 (1)	0.038 (1)	0.010 (1)	0.007 (1)
H207	0.042 (1)	0.032 (1)	0.028 (1)	0.023 (1)	0.000 (1)	0.003 (1)
H208A	0.046 (2)	0.034 (2)	0.030 (2)	0.024 (2)	0.007 (1)	0.010 (1)
H208B	0.046 (2)	0.034 (2)	0.030 (2)	0.024 (2)	0.007 (1)	0.010 (1)
H209	0.048 (2)	0.046 (2)	0.029 (2)	0.033 (2)	0.003 (1)	0.006 (1)
H211A	0.045 (1)	0.042 (1)	0.026 (1)	0.028 (1)	−0.004 (1)	0.001 (1)
H211B	0.045 (1)	0.042 (1)	0.026 (1)	0.028 (1)	−0.004 (1)	0.001 (1)
H211C	0.045 (1)	0.042 (1)	0.026 (1)	0.028 (1)	−0.004 (1)	0.001 (1)
H218A	0.075 (3)	0.044 (2)	0.038 (2)	0.042 (2)	−0.001 (2)	0.008 (2)
H218B	0.075 (3)	0.044 (2)	0.038 (2)	0.042 (2)	−0.001 (2)	0.008 (2)
H218C	0.075 (3)	0.044 (2)	0.038 (2)	0.042 (2)	−0.001 (2)	0.008 (2)
H219A	0.040 (1)	0.060 (2)	0.040 (1)	0.031 (1)	−0.001 (1)	0.002 (1)
H219B	0.040 (1)	0.060 (2)	0.040 (1)	0.031 (1)	−0.001 (1)	0.002 (1)
H219C	0.040 (1)	0.060 (2)	0.040 (1)	0.031 (1)	−0.001 (1)	0.002 (1)
H221A	0.049 (9)	0.080 (10)	0.072 (7)	0.036 (9)	−0.001 (8)	0.006 (8)
H221B	0.046 (5)	0.076 (4)	0.070 (4)	0.032 (4)	−0.007 (4)	0.000 (4)
H221C	0.047 (7)	0.077 (6)	0.068 (3)	0.034 (6)	−0.004 (2)	0.002 (3)
H222A	0.070 (3)	0.059 (3)	0.036 (2)	0.044 (2)	−0.006 (2)	0.004 (2)
H222B	0.070 (3)	0.059 (3)	0.036 (2)	0.044 (2)	−0.006 (2)	0.004 (2)
H222C	0.070 (3)	0.059 (3)	0.036 (2)	0.044 (2)	−0.006 (2)	0.004 (2)

Geometric parameters (Å, º)

C1—C2	1.516 (5)	C111—H111A	0.978 (8)
C1—O10	1.344 (4)	C111—H111B	0.978 (8)
C1—O12	1.205 (4)	C111—H111C	0.978 (8)
C2—C3	1.524 (5)	O113—C114	1.430 (4)
C2—O13	1.434 (4)	C114—C115	1.559 (5)
C2—H2	1.00 (5)	C114—O117	1.408 (4)
C3—C4	1.524 (5)	C114—C119	1.518 (2)
C3—O16	1.447 (4)	C115—O116	1.417 (4)
C3—H3	1.15 (5)	C115—O120	1.414 (4)
C4—C5	1.542 (5)	C115—C122	1.517 (2)
C4—H4A	0.93 (5)	O117—C118	1.429 (2)
C4—H4B	1.00 (5)	C118—H118A	0.982 (11)
C5—C6	1.503 (5)	C118—H118B	0.982 (11)
C5—H5A	1.02 (6)	C118—H118C	0.982 (11)
C5—H5B	1.15 (5)	C119—H119A	0.978 (8)
C6—C7	1.313 (6)	C119—H119B	0.978 (8)
C6—H6	0.98 (5)	C119—H119C	0.978 (8)
C7—C8	1.509 (5)	O120—C121	1.424 (2)
C7—H7	1.03 (5)	C121—H121A	0.982 (11)
C8—C9	1.518 (5)	C121—H121B	0.982 (11)
C8—H8A	1.04 (5)	C121—H121C	0.982 (11)
C8—H8B	0.99 (5)	C122—H122A	0.978 (8)
C9—O10	1.470 (4)	C122—H122B	0.978 (8)
C9—C11	1.513 (3)	C122—H122C	0.978 (8)
C9—H9	0.97 (5)	C201—C202	1.513 (4)
C11—H11A	0.978 (8)	C201—O210	1.350 (4)
C11—H11B	0.978 (8)	C201—O212	1.200 (4)
C11—H11C	0.978 (8)	C202—C203	1.531 (5)
O13—C14	1.430 (4)	C202—O213	1.427 (4)
C14—C15	1.555 (5)	C202—H202	0.96 (5)
C14—O17	1.420 (4)	C203—C204	1.513 (5)
C14—C19	1.518 (2)	C203—O216	1.441 (4)
C15—O16	1.417 (4)	C203—H203	0.99 (5)
C15—O20	1.416 (4)	C204—C205	1.537 (5)
C15—C22	1.517 (2)	C204—H204A	0.96 (5)
O17—C18	1.429 (2)	C204—H204B	1.01 (5)
C18—H18A	0.982 (11)	C205—C206	1.509 (5)
C18—H18B	0.982 (11)	C205—H205A	1.08 (5)
C18—H18C	0.982 (11)	C205—H205B	1.01 (5)
C19—H19A	0.978 (8)	C206—C207	1.323 (5)
C19—H19B	0.978 (8)	C206—H206	1.02 (5)
C19—H19C	0.978 (8)	C207—C208	1.497 (5)
O20—C21	1.424 (2)	C207—H207	1.16 (5)
C21—H21A	0.982 (11)	C208—C209	1.526 (5)
C21—H21B	0.982 (11)	C208—H208A	1.07 (5)
C21—H21C	0.982 (11)	C208—H208B	1.02 (5)
C22—H22A	0.978 (8)	C209—O210	1.474 (4)
C22—H22B	0.978 (8)	C209—C211	1.513 (3)
C22—H22C	0.978 (8)	C209—H209	1.03 (5)
C101—C102	1.523 (4)	C211—H211A	0.978 (8)
C101—O110	1.325 (4)	C211—H211B	0.978 (8)
C101—O112	1.201 (4)	C211—H211C	0.978 (8)
C102—C103	1.530 (4)	O213—C214	1.433 (4)
C102—O113	1.422 (4)	C214—C215	1.549 (5)
C102—H102	0.93 (5)	C214—O217	1.423 (4)
C103—C104	1.531 (5)	C214—C219	1.518 (2)
C103—O116	1.427 (4)	C215—O216	1.419 (4)
C103—H103	0.97 (5)	C215—O220	1.411 (4)
C104—C105	1.551 (5)	C215—C222	1.517 (2)
C104—H104A	1.01 (5)	O217—C218	1.429 (2)
C104—H104B	1.05 (5)	C218—H218A	0.982 (11)
C105—C106	1.504 (6)	C218—H218B	0.982 (11)
C105—H105A	1.01 (6)	C218—H218C	0.982 (11)
C105—H105B	0.82 (6)	C219—H219A	0.978 (8)
C106—C107	1.335 (6)	C219—H219B	0.978 (8)
C106—H106	0.99 (5)	C219—H219C	0.978 (8)
C107—C108	1.505 (5)	O220—C221	1.424 (2)
C107—H107	1.09 (5)	C221—H221A	0.982 (11)
C108—C109	1.521 (5)	C221—H221B	0.982 (11)
C108—H108A	1.02 (5)	C221—H221C	0.982 (11)
C108—H108B	0.96 (5)	C222—H222A	0.978 (8)
C109—O110	1.472 (4)	C222—H222B	0.978 (8)
C109—C111	1.513 (3)	C222—H222C	0.978 (8)
C109—H109	1.04 (5)
C2—C1—O10	109.4 (3)	C109—C111—H111A	110.1 (5)
C2—C1—O12	126.1 (3)	C109—C111—H111B	110.1 (5)
O10—C1—O12	124.5 (3)	C109—C111—H111C	110.1 (5)
C1—C2—C3	111.4 (3)	H111A—C111—H111B	108.8 (5)
C1—C2—O13	106.4 (2)	H111A—C111—H111C	108.8 (5)
C1—C2—H2	110 (3)	H111B—C111—H111C	108.8 (5)
C3—C2—O13	110.7 (3)	C102—O113—C114	113.2 (2)
C3—C2—H2	115 (3)	O113—C114—C115	109.7 (2)
O13—C2—H2	103 (3)	O113—C114—O117	110.9 (2)
C2—C3—C4	113.7 (3)	O113—C114—C119	105.8 (2)
C2—C3—O16	106.3 (3)	C115—C114—O117	103.8 (2)
C2—C3—H3	109 (2)	C115—C114—C119	112.8 (3)
C4—C3—O16	106.3 (3)	O117—C114—C119	113.9 (3)
C4—C3—H3	115 (2)	C114—C115—O116	109.7 (2)
O16—C3—H3	105 (2)	C114—C115—O120	103.9 (2)
C3—C4—C5	114.1 (3)	C114—C115—C122	113.4 (3)
C3—C4—H4A	111 (3)	O116—C115—O120	111.0 (3)
C3—C4—H4B	104 (3)	O116—C115—C122	105.3 (2)
C5—C4—H4A	114 (3)	O120—C115—C122	113.7 (3)
C5—C4—H4B	116 (3)	C103—O116—C115	114.8 (2)
H4A—C4—H4B	96 (4)	C114—O117—C118	115.0 (2)
C4—C5—C6	113.1 (3)	O117—C118—H118A	108.7 (7)
C4—C5—H5A	111 (3)	O117—C118—H118B	108.7 (7)
C4—C5—H5B	105 (3)	O117—C118—H118C	108.7 (7)
C6—C5—H5A	104 (3)	H118A—C118—H118B	110.3 (7)
C6—C5—H5B	115 (3)	H118A—C118—H118C	110.3 (7)
H5A—C5—H5B	108 (4)	H118B—C118—H118C	110.3 (7)
C5—C6—C7	126.4 (4)	C114—C119—H119A	110.1 (5)
C5—C6—H6	106 (3)	C114—C119—H119B	110.1 (5)
C7—C6—H6	128 (3)	C114—C119—H119C	110.1 (5)
C6—C7—C8	125.7 (4)	H119A—C119—H119B	108.8 (5)
C6—C7—H7	110 (3)	H119A—C119—H119C	108.8 (5)
C8—C7—H7	124 (3)	H119B—C119—H119C	108.8 (5)
C7—C8—C9	114.1 (3)	C115—O120—C121	116.5 (3)
C7—C8—H8A	112 (3)	O120—C121—H121A	108.7 (7)
C7—C8—H8B	118 (3)	O120—C121—H121B	108.7 (7)
C9—C8—H8A	106 (3)	O120—C121—H121C	108.7 (7)
C9—C8—H8B	105 (3)	H121A—C121—H121B	110.3 (7)
H8A—C8—H8B	100 (4)	H121A—C121—H121C	110.3 (7)
C8—C9—O10	109.6 (3)	H121B—C121—H121C	110.3 (7)
C8—C9—C11	113.9 (3)	C115—C122—H122A	110.1 (5)
C8—C9—H9	109 (3)	C115—C122—H122B	110.1 (5)
O10—C9—C11	104.9 (2)	C115—C122—H122C	110.1 (5)
O10—C9—H9	108 (3)	H122A—C122—H122B	108.8 (5)
C11—C9—H9	112 (3)	H122A—C122—H122C	108.8 (5)
C1—O10—C9	117.2 (2)	H122B—C122—H122C	108.8 (5)
C9—C11—H11A	110.1 (5)	C202—C201—O210	110.0 (3)
C9—C11—H11B	110.1 (5)	C202—C201—O212	126.2 (3)
C9—C11—H11C	110.1 (5)	O210—C201—O212	123.7 (3)
H11A—C11—H11B	108.8 (5)	C201—C202—C203	111.2 (3)
H11A—C11—H11C	108.8 (5)	C201—C202—O213	106.5 (2)
H11B—C11—H11C	108.8 (5)	C201—C202—H202	113 (3)
C2—O13—C14	112.4 (2)	C203—C202—O213	110.5 (3)
O13—C14—C15	110.2 (2)	C203—C202—H202	111 (3)
O13—C14—O17	109.8 (2)	O213—C202—H202	104 (3)
O13—C14—C19	105.1 (2)	C202—C203—C204	113.6 (3)
C15—C14—O17	105.1 (2)	C202—C203—O216	106.7 (3)
C15—C14—C19	114.0 (3)	C202—C203—H203	107 (3)
O17—C14—C19	112.7 (3)	C204—C203—O216	106.8 (3)
C14—C15—O16	110.3 (3)	C204—C203—H203	115 (3)
C14—C15—O20	104.1 (2)	O216—C203—H203	108 (3)
C14—C15—C22	112.8 (3)	C203—C204—C205	113.4 (3)
O16—C15—O20	111.5 (3)	C203—C204—H204A	110 (3)
O16—C15—C22	105.1 (3)	C203—C204—H204B	109 (3)
O20—C15—C22	113.1 (3)	C205—C204—H204A	115 (3)
C3—O16—C15	114.8 (2)	C205—C204—H204B	106 (3)
C14—O17—C18	116.8 (2)	H204A—C204—H204B	102 (4)
O17—C18—H18A	108.7 (7)	C204—C205—C206	112.8 (3)
O17—C18—H18B	108.7 (7)	C204—C205—H205A	111 (3)
O17—C18—H18C	108.7 (7)	C204—C205—H205B	109 (3)
H18A—C18—H18B	110.3 (7)	C206—C205—H205A	105 (3)
H18A—C18—H18C	110.3 (7)	C206—C205—H205B	115 (3)
H18B—C18—H18C	110.3 (7)	H205A—C205—H205B	104 (4)
C14—C19—H19A	110.1 (5)	C205—C206—C207	126.5 (3)
C14—C19—H19B	110.1 (5)	C205—C206—H206	116 (3)
C14—C19—H19C	110.1 (5)	C207—C206—H206	118 (3)
H19A—C19—H19B	108.8 (5)	C206—C207—C208	125.0 (3)
H19A—C19—H19C	108.8 (5)	C206—C207—H207	116 (2)
H19B—C19—H19C	108.8 (5)	C208—C207—H207	119 (2)
C15—O20—C21	115.9 (3)	C207—C208—C209	113.6 (3)
O20—C21—H21A	108.7 (7)	C207—C208—H208A	113 (3)
O20—C21—H21B	108.7 (7)	C207—C208—H208B	117 (3)
O20—C21—H21C	108.7 (7)	C209—C208—H208A	106 (3)
H21A—C21—H21B	110.3 (7)	C209—C208—H208B	100 (3)
H21A—C21—H21C	110.3 (7)	H208A—C208—H208B	107 (4)
H21B—C21—H21C	110.3 (7)	C208—C209—O210	109.9 (3)
C15—C22—H22A	110.1 (5)	C208—C209—C211	112.9 (3)
C15—C22—H22B	110.1 (5)	C208—C209—H209	112 (3)
C15—C22—H22C	110.1 (5)	O210—C209—C211	105.5 (2)
H22A—C22—H22B	108.8 (5)	O210—C209—H209	105 (3)
H22A—C22—H22C	108.8 (5)	C211—C209—H209	111 (3)
H22B—C22—H22C	108.8 (5)	C201—O210—C209	116.6 (2)
C102—C101—O110	110.1 (3)	C209—C211—H211A	110.1 (5)
C102—C101—O112	123.9 (3)	C209—C211—H211B	110.1 (5)
O110—C101—O112	125.9 (3)	C209—C211—H211C	110.1 (5)
C101—C102—C103	112.1 (2)	H211A—C211—H211B	108.8 (5)
C101—C102—O113	107.7 (2)	H211A—C211—H211C	108.8 (5)
C101—C102—H102	106 (3)	H211B—C211—H211C	108.8 (5)
C103—C102—O113	110.5 (3)	C202—O213—C214	112.0 (2)
C103—C102—H102	109 (3)	O213—C214—C215	109.3 (2)
O113—C102—H102	112 (3)	O213—C214—O217	110.1 (3)
C102—C103—C104	113.1 (3)	O213—C214—C219	105.3 (2)
C102—C103—O116	107.6 (2)	C215—C214—O217	104.9 (2)
C102—C103—H103	107 (3)	C215—C214—C219	114.2 (3)
C104—C103—O116	106.7 (3)	O217—C214—C219	113.1 (3)
C104—C103—H103	112 (3)	C214—C215—O216	110.4 (2)
O116—C103—H103	110 (3)	C214—C215—O220	104.8 (2)
C103—C104—C105	113.2 (3)	C214—C215—C222	112.7 (3)
C103—C104—H104A	108 (2)	O216—C215—O220	111.2 (3)
C103—C104—H104B	113 (2)	O216—C215—C222	105.0 (3)
C105—C104—H104A	104 (3)	O220—C215—C222	112.9 (3)
C105—C104—H104B	104 (2)	C203—O216—C215	114.4 (2)
H104A—C104—H104B	114 (3)	C214—O217—C218	116.4 (3)
C104—C105—C106	112.8 (3)	O217—C218—H218A	108.7 (7)
C104—C105—H105A	111 (3)	O217—C218—H218B	108.7 (7)
C104—C105—H105B	106 (4)	O217—C218—H218C	108.7 (7)
C106—C105—H105A	112 (3)	H218A—C218—H218B	110.3 (7)
C106—C105—H105B	111 (4)	H218A—C218—H218C	110.3 (7)
H105A—C105—H105B	104 (5)	H218B—C218—H218C	110.3 (7)
C105—C106—C107	126.3 (3)	C214—C219—H219A	110.1 (5)
C105—C106—H106	115 (3)	C214—C219—H219B	110.1 (5)
C107—C106—H106	119 (3)	C214—C219—H219C	110.1 (5)
C106—C107—C108	124.6 (3)	H219A—C219—H219B	108.8 (5)
C106—C107—H107	127 (2)	H219A—C219—H219C	108.8 (5)
C108—C107—H107	108 (2)	H219B—C219—H219C	108.8 (5)
C107—C108—C109	113.2 (3)	C215—O220—C221	116.2 (3)
C107—C108—H108A	109 (3)	O220—C221—H221A	108.7 (7)
C107—C108—H108B	107 (3)	O220—C221—H221B	108.7 (7)
C109—C108—H108A	109 (3)	O220—C221—H221C	108.7 (7)
C109—C108—H108B	110 (3)	H221A—C221—H221B	110.3 (7)
H108A—C108—H108B	109 (4)	H221A—C221—H221C	110.3 (7)
C108—C109—O110	108.7 (3)	H221B—C221—H221C	110.3 (7)
C108—C109—C111	114.4 (3)	C215—C222—H222A	110.1 (5)
C108—C109—H109	112 (3)	C215—C222—H222B	110.1 (5)
O110—C109—C111	106.2 (2)	C215—C222—H222C	110.1 (5)
O110—C109—H109	103 (3)	H222A—C222—H222B	108.8 (5)
C111—C109—H109	111 (3)	H222A—C222—H222C	108.8 (5)
C101—O110—C109	117.8 (2)	H222B—C222—H222C	108.8 (5)
C3—C2—C1—O10	100.5 (3)	C101—O110—C109—C111	−156.0 (3)
O13—C2—C1—O10	−138.7 (3)	C115—C114—O113—C102	55.0 (3)
C3—C2—C1—O12	−78.1 (4)	O117—C114—O113—C102	−59.2 (3)
O13—C2—C1—O12	42.7 (4)	C119—C114—O113—C102	176.9 (3)
C9—O10—C1—C2	−172.7 (3)	O116—C115—C114—O113	−51.6 (3)
C9—O10—C1—O12	5.9 (5)	O120—C115—C114—O113	67.1 (3)
C4—C3—C2—C1	−66.0 (4)	C122—C115—C114—O113	−168.9 (2)
O16—C3—C2—C1	177.4 (3)	O116—C115—C114—O117	67.0 (3)
C4—C3—C2—O13	175.8 (3)	O120—C115—C114—O117	−174.2 (2)
O16—C3—C2—O13	59.2 (3)	C122—C115—C114—O117	−50.3 (3)
C14—O13—C2—C1	178.4 (3)	O116—C115—C114—C119	−169.3 (2)
C14—O13—C2—C3	−60.3 (3)	O120—C115—C114—C119	−50.5 (3)
C5—C4—C3—C2	85.2 (4)	C122—C115—C114—C119	73.4 (3)
C5—C4—C3—O16	−158.2 (3)	C118—O117—C114—O113	−63.0 (3)
C15—O16—C3—C2	−59.0 (3)	C118—O117—C114—C115	179.2 (3)
C15—O16—C3—C4	179.5 (3)	C118—O117—C114—C119	56.2 (4)
C6—C5—C4—C3	−135.4 (3)	C103—O116—C115—C114	56.3 (3)
C7—C6—C5—C4	114.9 (4)	C103—O116—C115—O120	−58.1 (3)
C8—C7—C6—C5	−0.2 (7)	C103—O116—C115—C122	178.6 (3)
C9—C8—C7—C6	−91.6 (5)	C121—O120—C115—C114	−176.4 (3)
O10—C9—C8—C7	55.5 (4)	C121—O120—C115—O116	−58.5 (3)
C11—C9—C8—C7	−61.6 (4)	C121—O120—C115—C122	59.9 (4)
C1—O10—C9—C8	80.4 (3)	C203—C202—C201—O210	99.0 (3)
C1—O10—C9—C11	−157.0 (3)	O213—C202—C201—O210	−140.5 (3)
C15—C14—O13—C2	54.3 (3)	C203—C202—C201—O212	−78.6 (4)
O17—C14—O13—C2	−61.0 (3)	O213—C202—C201—O212	41.9 (4)
C19—C14—O13—C2	177.5 (3)	C209—O210—C201—C202	−171.4 (3)
O16—C15—C14—O13	−50.6 (3)	C209—O210—C201—O212	6.3 (5)
O20—C15—C14—O13	69.2 (3)	C204—C203—C202—C201	−65.8 (4)
C22—C15—C14—O13	−167.8 (3)	O216—C203—C202—C201	176.8 (2)
O16—C15—C14—O17	67.6 (3)	C204—C203—C202—O213	176.0 (3)
O20—C15—C14—O17	−172.6 (2)	O216—C203—C202—O213	58.7 (3)
C22—C15—C14—O17	−49.5 (3)	C214—O213—C202—C201	177.9 (3)
O16—C15—C14—C19	−168.5 (2)	C214—O213—C202—C203	−61.1 (3)
O20—C15—C14—C19	−48.7 (3)	C205—C204—C203—C202	88.6 (4)
C22—C15—C14—C19	74.4 (3)	C205—C204—C203—O216	−154.1 (3)
C18—O17—C14—O13	−69.2 (3)	C215—O216—C203—C202	−58.1 (3)
C18—O17—C14—C15	172.3 (2)	C215—O216—C203—C204	−179.9 (3)
C18—O17—C14—C19	47.6 (4)	C206—C205—C204—C203	−136.9 (3)
C3—O16—C15—C14	55.6 (3)	C207—C206—C205—C204	112.3 (4)
C3—O16—C15—O20	−59.5 (3)	C208—C207—C206—C205	0.9 (6)
C3—O16—C15—C22	177.5 (3)	C209—C208—C207—C206	−93.3 (4)
C21—O20—C15—C14	−175.2 (3)	O210—C209—C208—C207	57.3 (4)
C21—O20—C15—O16	−56.2 (3)	C211—C209—C208—C207	−60.1 (4)
C21—O20—C15—C22	62.0 (4)	C201—O210—C209—C208	79.0 (3)
C103—C102—C101—O110	98.2 (3)	C201—O210—C209—C211	−159.0 (3)
O113—C102—C101—O110	−140.0 (3)	C215—C214—O213—C202	56.4 (3)
C103—C102—C101—O112	−80.3 (4)	O217—C214—O213—C202	−58.3 (3)
O113—C102—C101—O112	41.5 (4)	C219—C214—O213—C202	179.5 (3)
C109—O110—C101—C102	−173.5 (2)	O216—C215—C214—O213	−52.6 (3)
C109—O110—C101—O112	4.9 (5)	O220—C215—C214—O213	67.2 (3)
C104—C103—C102—C101	−64.9 (4)	C222—C215—C214—O213	−169.7 (3)
O116—C103—C102—C101	177.5 (2)	O216—C215—C214—O217	65.4 (3)
C104—C103—C102—O113	175.0 (3)	O220—C215—C214—O217	−174.8 (2)
O116—C103—C102—O113	57.3 (3)	C222—C215—C214—O217	−51.6 (3)
C114—O113—C102—C101	178.4 (2)	O216—C215—C214—C219	−170.2 (2)
C114—O113—C102—C103	−58.8 (3)	O220—C215—C214—C219	−50.4 (3)
C105—C104—C103—C102	86.0 (4)	C222—C215—C214—C219	72.7 (4)
C105—C104—C103—O116	−155.8 (3)	C218—O217—C214—O213	−61.4 (3)
C115—O116—C103—C102	−58.5 (3)	C218—O217—C214—C215	−178.9 (3)
C115—O116—C103—C104	179.8 (3)	C218—O217—C214—C219	56.0 (4)
C106—C105—C104—C103	−137.2 (3)	C203—O216—C215—C214	56.3 (3)
C107—C106—C105—C104	114.2 (4)	C203—O216—C215—O220	−59.6 (3)
C108—C107—C106—C105	0.5 (6)	C203—O216—C215—C222	178.0 (3)
C109—C108—C107—C106	−92.8 (5)	C221—O220—C215—C214	−176.2 (3)
O110—C109—C108—C107	58.3 (4)	C221—O220—C215—O216	−57.0 (3)
C111—C109—C108—C107	−60.3 (4)	C221—O220—C215—C222	60.7 (4)
C101—O110—C109—C108	80.4 (3)