Pregnenolone hemisuccinate: a P1 structure with Z' = 4

The structure of the title compound, C₂₅H₃₆O₅, was refined in space group P1, with Z' = 4. The high value for Z' is due to a degree of free rotation around the ester bond C-O at the 3 position of the steroidal A-D nucleus.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.066
• wR factor = 0.191
• Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level B
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      0.961
            Test value =      0.800
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density ....       4.47
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       0.96 e/A   3
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.39 Ratio
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....         C1
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....        C11
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....        C12
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....       C107
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....        C21
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....        C25
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....       C225

Alert level C
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 8 for a
            non-centrosymmetric structure, where ZMAX < 18
            sine(theta)/lambda               -0.1862
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   7.3845
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.38
PLAT213_ALERT_2_C Atom O22     has ADP max/min Ratio .............       3.30 prolat
PLAT213_ALERT_2_C Atom C11     has ADP max/min Ratio .............       3.10 prolat
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.18 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.50 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.24 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C213   -   C218     =       6.08 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C24
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....       C116
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....       C124
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....       O320
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....       C324
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C5
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C8
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C9
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C10
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C13
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C23
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C113
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C123
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C125
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C128
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C228
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C321
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C325
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C328
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.50
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.14
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.22
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........        O29
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O327   -   H327     =       1.04 Ang.
PLAT362_ALERT_2_C Short  C(sp3)-C(sp2) Bond  C28    -   C30      =       1.37 Ang.

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           25.00
           From the CIF: _reflns_number_total               7990
           Count of symmetry unique reflns         8015
           Completeness (_total/calc)             99.69%
           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
  11 ALERT level B = Potentially serious problem
  36 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

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S1. Comment

As part of our interest in the synthesis of hydrophilic steroid derivatives, we have studied the monoesterification of pregnenolone (Δ⁵-pregnen-3β-ol-20-one) with anhydride of dicarboxylic acids, aiming to obtain hemiesters able to form water soluble salts. Pregnenolone, progesterone and the vast majority of corticosteroids belong to the pregnanes, a family considered to be the largest individual group of steroids. Furthermore, pregnenolone is a key intermediate in the biosynthesis of cortisol and related steroids, included in the general metabolism of cholesterol (Voet & Voet, 1990). Some hemisuccinate derivatives of these compounds have been studied, although with poor structural characterization. For example, the powder X-ray diffraction pattern (Parson, 1966) and the hypnotic properties (Gyermek et al., 1968) of the hemisuccinate of progesterone have been described.

In the case of pregnenolone, the formation of esters using the alcoholysis of anhydrides has two possible outcomes, viz. the esterification of the OH group at C3 or of the ketone at C28, after reduction to the corresponding alcohol. In this work, we explore the first alternative. The title compound, (I), was prepared starting from pregnenolone, succinic anhydride and pyridine (see Experimental).

The asymmetric unit of (I) contains four independent molecules, with no evidence of pseudo- or non-crystallographic symmetry. Crystals belonging to this class, namely Z' = 4 in space group P1, are not uncommon, with 153 occurrences reported in the Cambridge Structural Database (CSD, Version 5.24; Allen & Kennard, 1993). Cholesterol hemimethanol solvate, for which the structure was recently redetermined (Shieh & Nordman, 2002), belongs to this class.

Each independent molecule (Figs. 1–4) adopts a similar geometry (Table 1), with the expected all-trans A/B/C/D junctions and C5═C6 bond lengths in the range 1.290 (8)–1.327 (7) Å (Table 1). The geometry of the A–D system is identical to that observed for two previously X-ray characterized pregnenolone derivatives (Kolb et al., 1987). The four molecules in the asymmetric unit are almost parallel to one another, approximately along the b axis of the unit cell. Intermolecular contacts are limited to classical double hydrogen bonds (Moulton & Zaworotko, 2001) involving free carboxylic acid groups (Table 2), forming two independent discrete dimers in the cell (Fig. 5). All four molecules have the same absolute configurations for the chiral centers, e.g. 3S, 8R, 9S, 10R, 13S, 14S and 17S for the C1-containing molecule. This unique hand precludes the possibility of a centrosymmetric structure, making the space group assignation unambiguous.

It is noteworthy that the X-ray structure of pregnenolone was previously reported in space group P2₁ with Z' = 1 (CSD refcode PREGOL). One reason that (I) crystallizes with Z' = 4 can be found in the succinic moiety. A least-squares fit (Sheldrick, 1998) of the four independent molecules, using all non-H atoms, clearly indicates that substantial deviations are observed for the carbonyl atoms O22, O122, O222 and O322. For instance, comparing the C1-molecule with the others, the r.m.s. deviations are 0.388, 0.317 and 0.324 Å for the C101-, C201- and C301-molecules, respectively, while the deviations from O22 are 1.245, 0.982 and 1.122 Å for O122, O222 and O322, respectively. These deviations are a consequence of the rotational freedom around the O20—C21 σ bond, whereas the A–D steroidal nucleus is unaffected by the flexibility of the lateral chain at C3 (Fig. 6). This is very probably valid for any steroid derivative, for which five- and six-membered rings are built-up essentially of Csp³ atoms, giving a rigid core.

Crystal structures with Z'>1 are generally unwelcome for X-ray single-crystal characterization, for the following two reasons: (i) for a given molecular complexity, the size of the unit cell, which is directly correlated to the size of the diffraction sphere, increases, lengthening data collection; and (ii) molecules in these crystals are generally not very densely packed, giving poorly diffracting samples (Lehmler et al., 2002). This phenomenon is also associated with low melting point compounds, sometimes close to room temperature (McCourt et al., 1996). However, these structures are of interest, because large Z' values do not appear accidentally. They may be related to packing conflicts (Kitaigorodskii, 1973), non-crystallographic symmetry induced by intermolecular contacts, cocrystallization phenomenon, etc. The limiting case, Z' → ∞, can be considered as a frontier between the crystalline and glassy states (Lehmler et al., 2002). Based on the same concept, soft matter, including nematic phases, would be characterized by Z → ∞.

In conclusion, we have found that for the pregnenolone derivative reported here, a Z' > 1 structure was obtained because of the contrast between a rigid core and a lateral chain with a high degree of rotational freedom. Obviously, this should be considered as an a posteriori explination as it is almost always not possible to predict the Z' value that will be observed in the crystalline state.

S2. Experimental

In a round-bottomed flask, pregnenolone (1 g, 3.16 mmol) was dissolved in pyridine (20 ml) and succinic anhydride (3.6 g, 36 mmol) was added under a nitrogen atmosphere with magnetic stirring. The reaction was stirred at 373 K for 2.5 h. After cooling to room temperature, the mixture was poured over 100 ml of distilled water and the pH adjusted to 3 with dilute HCl (1:3). The white solid was filtered off, washed repeatedly with distilled water and dried at 333 K under vacuum to obtain 1.19 g of (I) as white microcrystals (yield 90%, m. p. 452–454 K). Analysis found: C 71.9, H 8.6, O 19.1%; calculated for C₂₅H₃₆O₅: C 72.1, H 8.7, O 19.2%. Spectroscopic data are in agreement with the X-ray structure. IR (CsI pellets) ν_(C═O) 1734, 1704 cm⁻¹, ν_(C—O) 1322, 1090 cm⁻¹; FAB⁺ m/z 417 [M⁺, 13%]; ¹³C NMR displacement for C3, pregnenolone: δ = 71.65 p.p.m., (I): δ = 74.41 p.p.m.

S3. Refinement

Due to the poor data-to-parameters ratio, non-H atoms were refined anisotropically, with atoms closer than 1.7 Å restrained, with an effective standard uncertainty of 0.04 Ų, to have the same U^ij components. H atoms bonded to sp³– or sp²-hybridized C atoms were placed at idealized positions. H atoms of the hydroxyl groups were found in difference maps. In order to avoid H···H bumping involving H30C belonging to the C30 methyl of the acetyl group in the first independent molecule, this methyl was first allowed to rotate about the C28—C30 bond, afterwards its torsion geometry was fixed. In the final cycles, all H atoms were constrained to ride on their parent atoms, with U_iso(H) = xU_eq(parent), where constrained distances (Å) and x parameters are: aromatic C—H 0.93 and x = 1.2, methine C—H 0.98 and x = 1.2, methylene C—H 0.97 and x = 1.2, methyl C—H 0.98 and x = 1.5, and hydroxyl O—H distance found from difference maps and x = 1.5. The highest residual peak observed in the final difference map is located in the vicinity of the C28/O29/C30 acetyl group, at 1.67 Å from C28. Its quite large value is attributable to the fact that this group displays large thermal motions. The U_eq parameter for O29, for example, is the largest observed for the overall asymmetric unit, U_eq = 0.224 (5) Ų.

Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury 1.1.2 (CCDC, 2002); software used to prepare material for publication: SHELXTL-Plus.

Figures

	Fig. 1. The structure of the first independent molecule in the asymmetric unit of (I), with displacement ellipsoids at the 25% probability level. For clarity, H atoms are omitted except for the hydroxyl group.
	Fig. 2. The structure of the second independent molecule in the asymmetric unit of (I), with displacement ellipsoids at the 25% probability level. For clarity, H atoms are omitted except for the hydroxyl group. The numbering scheme is based on that adopted for the first independent molecule, with all atoms numbers shifted by 100.
	Fig. 3. The structure of the third independent molecule in the asymmetric unit of (I), with displacement ellipsoids at the 25% probability level. For clarity, H atoms are omitted except for the hydroxyl group. The numbering scheme is based on that adopted for the first independent molecule, with all atoms numbers shifted by 200.
	Fig. 4. The structure of the fourth independent molecule in the asymmetric unit of (I), with displacement ellipsoids at the 25% probability level. For clarity, H atoms are omitted except for the hydroxyl group. The numbering scheme is based on that adopted for the first independent molecule, with all atoms numbers shifted by 300.
	Fig. 5. The packing structure of (I). Eight molecules are displayed and intermolecular hydrogen bonds are represented with dotted lines. The four molecules within the unit cell constitute the asymmetric unit and the color codes are as follows: grey = C1-containing molecule; red = C101-containing molecule; green = C201-containing molecule; blue = C301-containing molecule. Symmetry codes for symmetry related molecules: grey = x, y + 2, z; red = x, y − 2, z − 1; green = x, y − 2, z; blue = x, y + 2, z + 1.
	Fig. 6. Best least-squares fit between the four independent molecules in (I). Atomic positions for the fitted molecules were computed using all non-H atoms by means of XP (Sheldrick, 1998) and plotted with Mercury (CCDC, 2002). Color codes are identical to those used in Fig. 5: grey = C1-molecule, red = C101-molecule, green = C201-molecule, blue = C301-molecule. Note the large deviations observed for O22, O122, O222 and O322 on the succinic moiety.

Succinic acid mono(17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14, 15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl) ester

Crystal data

C25H36O5	Z = 4
Mr = 416.54	F(000) = 904
Triclinic, P1	Dx = 1.213 Mg m^−3
Hall symbol: P 1	Melting point: 452-454 K K
a = 11.4692 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8174 (12) Å	Cell parameters from 50 reflections
c = 17.6837 (14) Å	θ = 2.4–12.0°
α = 96.925 (9)°	µ = 0.08 mm^−1
β = 104.907 (6)°	T = 298 K
γ = 95.201 (8)°	Irregular, colourless
V = 2280.7 (4) Å^3	0.5 × 0.3 × 0.3 mm

Data collection

Bruker P4 diffractometer	Rint = 0.031
Radiation source: fine-focus sealed tube, FN4	θmax = 25.0°, θmin = 1.8°
Graphite monochromator	h = −1→13
2θ/ω scans	k = −13→13
9296 measured reflections	l = −21→20
7990 independent reflections	2 standard reflections every 98 reflections
5778 reflections with I > 2σ(I)	intensity decay: 0.5%

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)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.191	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.26	(Δ/σ)max < 0.001
7990 reflections	Δρmax = 0.96 e Å^−3
1082 parameters	Δρmin = −0.22 e Å^−3
795 restraints	Extinction correction: SHELXTL-Plus, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0083 (17)

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 of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.6706 (8)	−0.0481 (7)	0.7730 (7)	0.140 (4)
H1A	0.5918	−0.0475	0.7837	0.168*
H1B	0.6653	−0.0178	0.7238	0.168*
C2	0.6981 (8)	−0.1730 (7)	0.7623 (7)	0.125 (3)
H2A	0.6954	−0.2071	0.8091	0.150*
H2B	0.6373	−0.2175	0.7174	0.150*
C3	0.8206 (8)	−0.1750 (5)	0.7490 (4)	0.087 (2)
H3A	0.8234	−0.1432	0.7007	0.104*
C4	0.9173 (7)	−0.1090 (5)	0.8195 (4)	0.0810 (18)
H4A	0.9966	−0.1103	0.8095	0.097*
H4B	0.9182	−0.1452	0.8660	0.097*
C5	0.8920 (5)	0.0151 (5)	0.8343 (3)	0.0639 (14)
C6	0.9754 (6)	0.1001 (6)	0.8398 (4)	0.0795 (18)
H6A	1.0501	0.0814	0.8341	0.095*
C7	0.9627 (6)	0.2240 (5)	0.8542 (4)	0.0715 (16)
H7A	0.9598	0.2565	0.8061	0.086*
H7B	1.0339	0.2629	0.8946	0.086*
C8	0.8507 (4)	0.2464 (4)	0.8802 (3)	0.0525 (12)
H8A	0.8654	0.2364	0.9360	0.063*
C9	0.7438 (5)	0.1585 (5)	0.8312 (4)	0.0772 (18)
H9A	0.7377	0.1652	0.7757	0.093*
C10	0.7673 (6)	0.0331 (5)	0.8410 (4)	0.0786 (18)
C11	0.6225 (6)	0.1858 (7)	0.8450 (8)	0.161 (5)
H11A	0.6213	0.1738	0.8981	0.193*
H11B	0.5569	0.1337	0.8079	0.193*
C12	0.6012 (7)	0.3133 (8)	0.8343 (9)	0.167 (5)
H12A	0.5981	0.3250	0.7805	0.200*
H12B	0.5242	0.3285	0.8441	0.200*
C13	0.7045 (6)	0.3948 (6)	0.8921 (5)	0.092 (2)
C14	0.8208 (5)	0.3678 (5)	0.8723 (3)	0.0570 (13)
H14A	0.8069	0.3736	0.8159	0.068*
C15	0.9135 (5)	0.4704 (5)	0.9155 (4)	0.0675 (15)
H15A	0.9756	0.4829	0.8881	0.081*
H15B	0.9521	0.4588	0.9692	0.081*
C16	0.8396 (6)	0.5724 (5)	0.9156 (4)	0.0785 (17)
H16A	0.8644	0.6276	0.8846	0.094*
H16B	0.8512	0.6106	0.9692	0.094*
C17	0.7057 (6)	0.5213 (6)	0.8787 (6)	0.100 (2)
H17A	0.6925	0.5191	0.8215	0.120*
C18	0.7144 (10)	0.3866 (8)	0.9819 (7)	0.136 (4)
H18A	0.7526	0.3203	0.9962	0.204*
H18B	0.6344	0.3798	0.9898	0.204*
H18C	0.7621	0.4545	1.0144	0.204*
C19	0.7605 (11)	−0.0003 (7)	0.9229 (6)	0.130 (4)
H19A	0.8262	0.0433	0.9641	0.195*
H19B	0.7666	−0.0808	0.9228	0.195*
H19C	0.6844	0.0161	0.9322	0.195*
O20	0.8426 (5)	−0.2954 (4)	0.7413 (3)	0.0918 (14)
C21	0.8937 (6)	−0.3318 (5)	0.6858 (4)	0.0723 (16)
O22	0.9151 (10)	−0.2736 (5)	0.6422 (6)	0.203 (5)
C23	0.9162 (6)	−0.4523 (5)	0.6856 (3)	0.0674 (15)
H23A	0.8457	−0.4972	0.6925	0.081*
H23B	0.9849	−0.4570	0.7300	0.081*
C24	0.9419 (9)	−0.5029 (6)	0.6106 (5)	0.095 (2)
H24A	0.8743	−0.4943	0.5665	0.114*
H24B	1.0135	−0.4581	0.6049	0.114*
C25	0.9617 (6)	−0.6237 (5)	0.6040 (4)	0.0687 (15)
O26	0.9666 (5)	−0.6815 (4)	0.6556 (3)	0.0868 (13)
O27	0.9703 (7)	−0.6656 (4)	0.5356 (3)	0.129 (2)
H27	0.9730	−0.7394	0.5203	0.193*
C28	0.6143 (8)	0.5881 (8)	0.8987 (9)	0.154 (5)
O29	0.6307 (9)	0.6800 (11)	0.9559 (7)	0.224 (5)
C30	0.5165 (8)	0.5820 (9)	0.8340 (7)	0.135 (4)
H30A	0.5051	0.5080	0.8022	0.202*
H30B	0.5311	0.6408	0.8033	0.202*
H30C	0.4450	0.5929	0.8512	0.202*
C101	0.3005 (5)	0.3165 (4)	0.5268 (3)	0.0603 (13)
H10A	0.2324	0.2813	0.4827	0.072*
H10B	0.2914	0.2848	0.5733	0.072*
C102	0.2944 (6)	0.4449 (5)	0.5403 (4)	0.0722 (16)
H10C	0.2957	0.4769	0.4925	0.087*
H10D	0.2191	0.4589	0.5531	0.087*
C103	0.4001 (6)	0.5018 (4)	0.6067 (3)	0.0617 (14)
H10E	0.3963	0.4712	0.6552	0.074*
C104	0.5205 (6)	0.4826 (5)	0.5899 (4)	0.0723 (16)
H10F	0.5290	0.5210	0.5457	0.087*
H10G	0.5866	0.5157	0.6358	0.087*
C105	0.5282 (5)	0.3555 (5)	0.5703 (3)	0.0628 (14)
C106	0.6222 (6)	0.3101 (5)	0.6044 (5)	0.095 (2)
H10H	0.6835	0.3594	0.6418	0.114*
C107	0.6443 (7)	0.1867 (5)	0.5909 (6)	0.112 (3)
H10I	0.6397	0.1511	0.6369	0.135*
H10J	0.7255	0.1837	0.5845	0.135*
C108	0.5509 (5)	0.1187 (4)	0.5171 (4)	0.0641 (14)
H10K	0.5732	0.1363	0.4695	0.077*
C109	0.4247 (4)	0.1545 (4)	0.5150 (3)	0.0492 (11)
H10L	0.4118	0.1438	0.5665	0.059*
C110	0.4186 (5)	0.2835 (4)	0.5095 (3)	0.0513 (11)
C111	0.3229 (5)	0.0730 (4)	0.4531 (3)	0.0620 (14)
H11C	0.2450	0.0910	0.4598	0.074*
H11D	0.3259	0.0872	0.4007	0.074*
C112	0.3303 (5)	−0.0538 (4)	0.4578 (3)	0.0573 (13)
H11E	0.3170	−0.0709	0.5075	0.069*
H11F	0.2666	−0.0994	0.4151	0.069*
C113	0.4528 (4)	−0.0865 (4)	0.4521 (3)	0.0503 (11)
C114	0.5481 (5)	−0.0098 (4)	0.5200 (4)	0.0640 (14)
H11G	0.5263	−0.0228	0.5686	0.077*
C115	0.6670 (6)	−0.0631 (5)	0.5232 (6)	0.097 (2)
H11H	0.7073	−0.0348	0.4860	0.117*
H11I	0.7223	−0.0465	0.5759	0.117*
C116	0.6227 (7)	−0.1930 (6)	0.4998 (6)	0.106 (3)
H11J	0.6525	−0.2247	0.4562	0.127*
H11K	0.6517	−0.2334	0.5443	0.127*
C117	0.4828 (5)	−0.2055 (4)	0.4752 (3)	0.0604 (13)
H11L	0.4546	−0.2160	0.5220	0.072*
C118	0.4697 (7)	−0.0759 (6)	0.3711 (4)	0.0844 (19)
H11M	0.4154	−0.1346	0.3326	0.127*
H11N	0.5522	−0.0848	0.3715	0.127*
H11O	0.4521	−0.0017	0.3580	0.127*
C119	0.4189 (7)	0.3091 (5)	0.4269 (3)	0.0797 (18)
H11P	0.4841	0.2761	0.4113	0.120*
H11Q	0.4299	0.3908	0.4276	0.120*
H11R	0.3428	0.2767	0.3900	0.120*
O120	0.3981 (4)	0.6263 (3)	0.6193 (2)	0.0691 (10)
C121	0.3312 (8)	0.6673 (6)	0.6611 (4)	0.090 (2)
O122	0.2560 (8)	0.6054 (5)	0.6816 (4)	0.130 (2)
C123	0.3360 (6)	0.7938 (4)	0.6721 (4)	0.0701 (16)
H12C	0.4188	0.8276	0.6781	0.084*
H12D	0.2847	0.8160	0.6249	0.084*
C124	0.2966 (8)	0.8411 (5)	0.7410 (4)	0.090 (2)
H12E	0.3495	0.8200	0.7881	0.108*
H12F	0.2150	0.8048	0.7356	0.108*
C125	0.2964 (6)	0.9682 (5)	0.7532 (4)	0.0663 (14)
O126	0.3080 (5)	1.0290 (3)	0.7052 (3)	0.0848 (13)
O127	0.2792 (6)	1.0076 (4)	0.8208 (3)	0.1082 (18)
H127	0.2739	1.0800	0.8346	0.162*
C128	0.4260 (6)	−0.3094 (5)	0.4113 (4)	0.0697 (15)
O129	0.4875 (5)	−0.3674 (5)	0.3810 (4)	0.132 (2)
C130	0.2937 (6)	−0.3363 (5)	0.3882 (4)	0.0810 (18)
H13A	0.2715	−0.4160	0.3659	0.121*
H13B	0.2587	−0.2895	0.3497	0.121*
H13C	0.2638	−0.3212	0.4339	0.121*
C201	0.7393 (6)	0.3831 (5)	0.3476 (5)	0.0783 (18)
H20A	0.6549	0.3517	0.3234	0.094*
H20B	0.7654	0.3533	0.3972	0.094*
C202	0.7467 (6)	0.5135 (5)	0.3656 (5)	0.0846 (19)
H20C	0.7121	0.5441	0.3175	0.101*
H20D	0.7005	0.5336	0.4031	0.101*
C203	0.8769 (5)	0.5642 (4)	0.3996 (3)	0.0613 (14)
H20E	0.9106	0.5351	0.4493	0.074*
C204	0.9507 (5)	0.5339 (4)	0.3425 (3)	0.0539 (12)
H20F	1.0348	0.5670	0.3655	0.065*
H20G	0.9196	0.5649	0.2940	0.065*
C205	0.9428 (4)	0.4038 (4)	0.3247 (3)	0.0473 (11)
C206	1.0432 (5)	0.3533 (4)	0.3400 (3)	0.0534 (12)
H20H	1.1170	0.4001	0.3617	0.064*
C207	1.0462 (4)	0.2275 (4)	0.3251 (3)	0.0547 (12)
H20I	1.0637	0.1984	0.3753	0.066*
H20J	1.1116	0.2130	0.3012	0.066*
C208	0.9276 (4)	0.1627 (4)	0.2713 (3)	0.0430 (10)
H20K	0.9215	0.1751	0.2167	0.052*
C209	0.8206 (4)	0.2078 (4)	0.2965 (3)	0.0490 (11)
H20L	0.8347	0.1995	0.3525	0.059*
C210	0.8159 (5)	0.3391 (4)	0.2927 (3)	0.0534 (12)
C211	0.6975 (5)	0.1340 (5)	0.2531 (4)	0.0728 (17)
H21A	0.6744	0.1467	0.1984	0.087*
H21B	0.6354	0.1586	0.2774	0.087*
C212	0.7027 (5)	0.0036 (4)	0.2557 (4)	0.0683 (16)
H21C	0.7134	−0.0108	0.3098	0.082*
H21D	0.6261	−0.0390	0.2238	0.082*
C213	0.8064 (4)	−0.0390 (4)	0.2252 (3)	0.0502 (12)
C214	0.9241 (4)	0.0357 (4)	0.2756 (3)	0.0428 (10)
H21E	0.9269	0.0283	0.3307	0.051*
C215	1.0260 (5)	−0.0278 (4)	0.2577 (4)	0.0634 (14)
H21F	1.0993	−0.0102	0.3014	0.076*
H21G	1.0445	−0.0078	0.2101	0.076*
C216	0.9740 (5)	−0.1557 (5)	0.2463 (4)	0.0707 (16)
H21H	0.9838	−0.1958	0.1976	0.085*
H21I	1.0162	−0.1919	0.2900	0.085*
C217	0.8397 (5)	−0.1600 (4)	0.2429 (4)	0.0611 (13)
H21J	0.8323	−0.1670	0.2962	0.073*
C218	0.7841 (7)	−0.0341 (5)	0.1377 (4)	0.0814 (18)
H21K	0.7062	−0.0759	0.1097	0.122*
H21L	0.8465	−0.0679	0.1190	0.122*
H21M	0.7855	0.0445	0.1289	0.122*
C219	0.7625 (6)	0.3604 (5)	0.2074 (4)	0.0766 (17)
H21N	0.8101	0.3294	0.1744	0.115*
H21O	0.7639	0.4415	0.2063	0.115*
H21P	0.6801	0.3237	0.1881	0.115*
O220	0.8801 (4)	0.6892 (3)	0.4156 (2)	0.0672 (10)
C221	0.9780 (6)	0.7478 (5)	0.4683 (3)	0.0615 (14)
O222	1.0639 (4)	0.7066 (3)	0.5018 (3)	0.0784 (12)
C223	0.9667 (6)	0.8746 (5)	0.4792 (4)	0.0777 (18)
H22A	1.0032	0.9107	0.4429	0.093*
H22B	0.8812	0.8846	0.4655	0.093*
C224	1.0240 (7)	0.9330 (5)	0.5593 (4)	0.0782 (18)
H22C	1.1102	0.9261	0.5722	0.094*
H22D	0.9900	0.8948	0.5958	0.094*
C225	1.0080 (6)	1.0568 (5)	0.5708 (3)	0.0670 (15)
O226	0.9956 (7)	1.1142 (4)	0.5189 (3)	0.1100 (19)
O227	1.0057 (6)	1.0975 (4)	0.6405 (3)	0.1071 (18)
H227	0.9991	1.1751	0.6552	0.161*
C228	0.7618 (6)	−0.2613 (6)	0.1877 (6)	0.094 (2)
O229	0.7984 (6)	−0.3193 (5)	0.1432 (5)	0.153 (3)
C230	0.6325 (8)	−0.2836 (7)	0.1951 (8)	0.149 (5)
H23C	0.6003	−0.3624	0.1745	0.224*
H23D	0.5825	−0.2342	0.1656	0.224*
H23E	0.6332	−0.2683	0.2498	0.224*
C301	0.1501 (5)	−0.0855 (4)	0.0273 (4)	0.0671 (15)
H30D	0.1140	−0.0575	−0.0217	0.081*
H30E	0.0928	−0.0817	0.0591	0.081*
C302	0.1682 (7)	−0.2114 (5)	0.0077 (4)	0.0809 (19)
H30F	0.1936	−0.2436	0.0564	0.097*
H30G	0.0916	−0.2548	−0.0236	0.097*
C303	0.2607 (7)	−0.2223 (5)	−0.0366 (4)	0.084 (2)
H30H	0.2337	−0.1941	−0.0873	0.100*
C304	0.3819 (6)	−0.1557 (5)	0.0113 (4)	0.0791 (18)
H30I	0.4119	−0.1888	0.0592	0.095*
H30J	0.4408	−0.1611	−0.0193	0.095*
C305	0.3677 (5)	−0.0305 (5)	0.0331 (3)	0.0573 (14)
C306	0.4430 (5)	0.0509 (5)	0.0191 (3)	0.0636 (14)
H30K	0.5015	0.0275	−0.0053	0.076*
C307	0.4423 (5)	0.1746 (5)	0.0387 (3)	0.0612 (14)
H30L	0.4161	0.2066	−0.0100	0.073*
H30M	0.5247	0.2100	0.0653	0.073*
C308	0.3594 (4)	0.2057 (4)	0.0915 (3)	0.0458 (11)
H30N	0.4022	0.2011	0.1465	0.055*
C309	0.2423 (4)	0.1197 (4)	0.0666 (3)	0.0456 (10)
H30O	0.2061	0.1231	0.0104	0.055*
C310	0.2664 (4)	−0.0054 (4)	0.0715 (3)	0.0485 (11)
C311	0.1486 (5)	0.1575 (4)	0.1095 (4)	0.0574 (13)
H31A	0.0728	0.1069	0.0870	0.069*
H31B	0.1774	0.1486	0.1648	0.069*
C312	0.1234 (5)	0.2813 (4)	0.1046 (3)	0.0569 (12)
H31C	0.0833	0.2883	0.0503	0.068*
H31D	0.0689	0.3008	0.1367	0.068*
C313	0.2394 (4)	0.3647 (4)	0.1331 (3)	0.0482 (11)
C314	0.3268 (4)	0.3267 (4)	0.0861 (3)	0.0487 (11)
H31E	0.2837	0.3263	0.0305	0.058*
C315	0.4297 (5)	0.4276 (5)	0.1065 (4)	0.0670 (15)
H31F	0.4910	0.4213	0.1546	0.080*
H31G	0.4679	0.4310	0.0637	0.080*
C316	0.3640 (5)	0.5328 (5)	0.1177 (4)	0.0700 (16)
H31H	0.4027	0.5785	0.1689	0.084*
H31I	0.3674	0.5802	0.0770	0.084*
C317	0.2325 (5)	0.4904 (4)	0.1124 (3)	0.0548 (12)
H31J	0.1864	0.4835	0.0567	0.066*
C318	0.2923 (6)	0.3709 (5)	0.2226 (3)	0.0641 (14)
H31K	0.3093	0.2960	0.2346	0.096*
H31L	0.2347	0.3973	0.2493	0.096*
H31M	0.3662	0.4234	0.2399	0.096*
C319	0.3065 (6)	−0.0300 (5)	0.1578 (3)	0.0677 (15)
H31N	0.3796	0.0196	0.1860	0.102*
H31O	0.3213	−0.1087	0.1577	0.102*
H31P	0.2434	−0.0163	0.1831	0.102*
O320	0.2853 (6)	−0.3420 (4)	−0.0499 (2)	0.1014 (18)
C321	0.2294 (6)	−0.4072 (5)	−0.1147 (4)	0.0652 (14)
O322	0.1502 (6)	−0.3744 (4)	−0.1636 (3)	0.117 (2)
C323	0.2577 (6)	−0.5258 (4)	−0.1201 (4)	0.0670 (15)
H32A	0.2041	−0.5705	−0.0973	0.080*
H32B	0.3404	−0.5261	−0.0884	0.080*
C324	0.2461 (8)	−0.5829 (5)	−0.2011 (4)	0.087 (2)
H32C	0.3046	−0.5413	−0.2221	0.105*
H32D	0.1657	−0.5762	−0.2338	0.105*
C325	0.2645 (5)	−0.7061 (5)	−0.2095 (3)	0.0595 (13)
O326	0.2692 (4)	−0.7646 (3)	−0.1583 (2)	0.0737 (11)
O327	0.2751 (6)	−0.7463 (3)	−0.2792 (3)	0.0997 (17)
H327	0.2932	−0.8307	−0.2855	0.150*
C328	0.1731 (6)	0.5703 (5)	0.1595 (3)	0.0677 (15)
O329	0.2282 (6)	0.6605 (4)	0.1963 (3)	0.1094 (17)
C330	0.0441 (8)	0.5409 (6)	0.1571 (5)	0.101 (2)
H33A	0.0012	0.6056	0.1459	0.151*
H33B	0.0389	0.5214	0.2074	0.151*
H33C	0.0085	0.4765	0.1166	0.151*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.093 (6)	0.070 (5)	0.211 (10)	0.011 (4)	−0.006 (6)	−0.057 (6)
C2	0.099 (6)	0.075 (5)	0.173 (8)	0.013 (4)	0.018 (6)	−0.045 (5)
C3	0.132 (6)	0.052 (4)	0.074 (4)	0.030 (4)	0.025 (4)	−0.004 (3)
C4	0.089 (4)	0.060 (4)	0.097 (5)	0.024 (3)	0.022 (4)	0.017 (3)
C5	0.070 (4)	0.063 (3)	0.064 (3)	0.018 (3)	0.024 (3)	0.013 (3)
C6	0.066 (4)	0.072 (4)	0.113 (5)	0.023 (3)	0.044 (4)	0.011 (3)
C7	0.065 (4)	0.064 (4)	0.098 (4)	0.013 (3)	0.041 (3)	0.017 (3)
C8	0.049 (3)	0.050 (3)	0.058 (3)	0.004 (2)	0.017 (2)	0.003 (2)
C9	0.055 (3)	0.064 (4)	0.103 (5)	0.009 (3)	0.018 (3)	−0.019 (3)
C10	0.073 (4)	0.062 (4)	0.098 (5)	0.009 (3)	0.028 (3)	−0.013 (3)
C11	0.049 (4)	0.085 (5)	0.308 (14)	−0.014 (4)	0.035 (6)	−0.088 (7)
C12	0.052 (4)	0.095 (6)	0.294 (13)	0.019 (4)	−0.008 (6)	−0.090 (7)
C13	0.051 (3)	0.064 (4)	0.152 (7)	0.006 (3)	0.033 (4)	−0.027 (4)
C14	0.048 (3)	0.060 (3)	0.061 (3)	0.007 (2)	0.014 (2)	0.002 (2)
C15	0.052 (3)	0.059 (3)	0.095 (4)	0.004 (3)	0.027 (3)	0.012 (3)
C16	0.073 (4)	0.061 (4)	0.095 (4)	0.003 (3)	0.018 (3)	0.000 (3)
C17	0.067 (4)	0.069 (4)	0.146 (7)	0.023 (3)	0.008 (4)	−0.022 (4)
C18	0.150 (8)	0.102 (6)	0.193 (10)	−0.009 (5)	0.138 (8)	−0.017 (6)
C19	0.197 (10)	0.080 (5)	0.147 (8)	−0.005 (6)	0.123 (8)	−0.003 (5)
O20	0.146 (4)	0.064 (3)	0.081 (3)	0.041 (3)	0.046 (3)	0.013 (2)
C21	0.092 (4)	0.054 (3)	0.080 (4)	0.019 (3)	0.033 (3)	0.015 (3)
O22	0.404 (14)	0.086 (4)	0.249 (9)	0.127 (6)	0.255 (10)	0.092 (5)
C23	0.092 (4)	0.047 (3)	0.063 (3)	0.013 (3)	0.022 (3)	0.001 (2)
C24	0.159 (7)	0.061 (4)	0.093 (5)	0.039 (4)	0.071 (5)	0.018 (3)
C25	0.098 (4)	0.051 (3)	0.060 (3)	0.018 (3)	0.021 (3)	0.009 (3)
O26	0.135 (4)	0.058 (2)	0.069 (3)	0.028 (2)	0.026 (3)	0.004 (2)
O27	0.253 (8)	0.071 (3)	0.097 (4)	0.054 (4)	0.092 (5)	0.021 (3)
C28	0.077 (5)	0.076 (5)	0.280 (14)	0.023 (4)	0.023 (7)	−0.044 (7)
O29	0.160 (8)	0.240 (11)	0.246 (11)	0.067 (8)	0.046 (7)	−0.074 (9)
C30	0.076 (6)	0.114 (7)	0.195 (10)	0.031 (5)	0.013 (6)	−0.013 (7)
C101	0.055 (3)	0.051 (3)	0.067 (3)	0.013 (2)	0.005 (3)	−0.002 (2)
C102	0.074 (4)	0.052 (3)	0.085 (4)	0.022 (3)	0.013 (3)	−0.001 (3)
C103	0.086 (4)	0.038 (3)	0.058 (3)	0.015 (3)	0.016 (3)	0.002 (2)
C104	0.075 (4)	0.042 (3)	0.088 (4)	0.006 (3)	0.007 (3)	−0.004 (3)
C105	0.061 (3)	0.047 (3)	0.075 (4)	0.014 (3)	0.009 (3)	0.004 (3)
C106	0.063 (4)	0.051 (3)	0.137 (6)	0.003 (3)	−0.018 (4)	−0.017 (4)
C107	0.077 (4)	0.045 (3)	0.167 (7)	0.010 (3)	−0.037 (5)	−0.017 (4)
C108	0.050 (3)	0.042 (3)	0.092 (4)	0.006 (2)	0.009 (3)	0.002 (3)
C109	0.053 (3)	0.041 (2)	0.051 (3)	0.011 (2)	0.006 (2)	0.005 (2)
C110	0.058 (3)	0.043 (3)	0.050 (3)	0.008 (2)	0.012 (2)	0.002 (2)
C111	0.057 (3)	0.052 (3)	0.070 (3)	0.013 (2)	0.006 (3)	0.002 (2)
C112	0.052 (3)	0.045 (3)	0.071 (3)	0.008 (2)	0.011 (3)	0.002 (2)
C113	0.051 (3)	0.041 (3)	0.063 (3)	0.008 (2)	0.022 (2)	0.008 (2)
C114	0.052 (3)	0.049 (3)	0.087 (4)	0.017 (2)	0.009 (3)	0.006 (3)
C115	0.057 (4)	0.053 (3)	0.170 (7)	0.021 (3)	0.011 (4)	0.000 (4)
C116	0.075 (4)	0.059 (4)	0.164 (7)	0.023 (3)	−0.001 (4)	−0.006 (4)
C117	0.063 (3)	0.042 (3)	0.074 (3)	0.012 (2)	0.014 (3)	0.003 (2)
C118	0.121 (6)	0.060 (4)	0.091 (4)	0.018 (4)	0.055 (4)	0.020 (3)
C119	0.137 (6)	0.045 (3)	0.064 (3)	0.022 (3)	0.032 (4)	0.017 (3)
O120	0.099 (3)	0.0391 (19)	0.075 (2)	0.0168 (19)	0.035 (2)	0.0010 (17)
C121	0.150 (7)	0.053 (4)	0.087 (4)	0.013 (4)	0.065 (5)	0.021 (3)
O122	0.196 (7)	0.075 (3)	0.153 (5)	0.026 (4)	0.104 (5)	0.024 (3)
C123	0.099 (4)	0.043 (3)	0.074 (4)	0.024 (3)	0.030 (3)	0.005 (3)
C124	0.150 (7)	0.050 (3)	0.096 (5)	0.028 (4)	0.070 (5)	0.017 (3)
C125	0.087 (4)	0.049 (3)	0.066 (4)	0.016 (3)	0.030 (3)	−0.001 (3)
O126	0.144 (4)	0.045 (2)	0.077 (3)	0.023 (2)	0.050 (3)	0.005 (2)
O127	0.200 (6)	0.060 (3)	0.087 (3)	0.041 (3)	0.071 (4)	0.010 (2)
C128	0.078 (4)	0.045 (3)	0.088 (4)	0.015 (3)	0.028 (3)	0.001 (3)
O129	0.100 (4)	0.089 (4)	0.191 (6)	0.030 (3)	0.036 (4)	−0.054 (4)
C130	0.089 (5)	0.052 (3)	0.094 (4)	0.001 (3)	0.021 (4)	−0.003 (3)
C201	0.059 (4)	0.055 (3)	0.128 (6)	0.017 (3)	0.042 (4)	0.001 (3)
C202	0.080 (4)	0.058 (4)	0.122 (5)	0.026 (3)	0.042 (4)	−0.007 (3)
C203	0.074 (4)	0.042 (3)	0.069 (3)	0.021 (3)	0.023 (3)	−0.003 (2)
C204	0.055 (3)	0.041 (3)	0.066 (3)	0.009 (2)	0.019 (2)	0.001 (2)
C205	0.051 (3)	0.042 (3)	0.047 (3)	0.007 (2)	0.010 (2)	0.0046 (19)
C206	0.046 (3)	0.046 (3)	0.063 (3)	0.007 (2)	0.010 (2)	−0.001 (2)
C207	0.036 (3)	0.046 (3)	0.078 (3)	0.005 (2)	0.011 (2)	0.001 (2)
C208	0.037 (2)	0.039 (2)	0.050 (2)	0.0014 (18)	0.007 (2)	0.0072 (19)
C209	0.043 (3)	0.042 (3)	0.062 (3)	0.009 (2)	0.015 (2)	0.004 (2)
C210	0.050 (3)	0.039 (2)	0.067 (3)	0.013 (2)	0.008 (2)	0.001 (2)
C211	0.044 (3)	0.050 (3)	0.119 (5)	0.008 (2)	0.017 (3)	0.001 (3)
C212	0.036 (3)	0.049 (3)	0.113 (5)	−0.005 (2)	0.016 (3)	0.006 (3)
C213	0.045 (3)	0.038 (3)	0.061 (3)	−0.001 (2)	0.004 (2)	0.006 (2)
C214	0.038 (2)	0.038 (2)	0.050 (3)	0.0051 (19)	0.009 (2)	0.0064 (19)
C215	0.046 (3)	0.046 (3)	0.100 (4)	0.012 (2)	0.022 (3)	0.006 (3)
C216	0.059 (3)	0.043 (3)	0.104 (5)	0.010 (2)	0.014 (3)	0.004 (3)
C217	0.057 (3)	0.039 (3)	0.080 (3)	0.004 (2)	0.006 (3)	0.007 (2)
C218	0.090 (4)	0.049 (3)	0.080 (4)	0.005 (3)	−0.015 (3)	−0.004 (3)
C219	0.076 (4)	0.055 (3)	0.082 (4)	0.015 (3)	−0.011 (3)	0.012 (3)
O220	0.073 (2)	0.046 (2)	0.079 (3)	0.0235 (18)	0.016 (2)	−0.0086 (18)
C221	0.073 (4)	0.051 (3)	0.060 (3)	0.022 (3)	0.018 (3)	−0.006 (3)
O222	0.088 (3)	0.058 (2)	0.081 (3)	0.026 (2)	0.012 (2)	−0.009 (2)
C223	0.090 (4)	0.046 (3)	0.087 (4)	0.023 (3)	0.009 (3)	−0.004 (3)
C224	0.117 (5)	0.045 (3)	0.067 (3)	0.017 (3)	0.015 (3)	0.004 (3)
C225	0.087 (4)	0.050 (3)	0.058 (3)	0.010 (3)	0.013 (3)	−0.005 (3)
O226	0.216 (6)	0.053 (3)	0.078 (3)	0.039 (3)	0.063 (4)	0.009 (2)
O227	0.197 (6)	0.061 (3)	0.067 (3)	0.038 (3)	0.038 (3)	0.001 (2)
C228	0.063 (4)	0.044 (3)	0.157 (7)	0.005 (3)	−0.005 (4)	0.015 (4)
O229	0.108 (5)	0.087 (4)	0.206 (7)	0.026 (3)	−0.021 (4)	−0.073 (4)
C230	0.079 (5)	0.073 (5)	0.265 (14)	−0.024 (4)	0.009 (7)	0.013 (7)
C301	0.063 (3)	0.046 (3)	0.082 (4)	0.010 (3)	0.008 (3)	−0.006 (3)
C302	0.094 (5)	0.045 (3)	0.091 (4)	0.014 (3)	0.006 (4)	0.001 (3)
C303	0.136 (6)	0.049 (3)	0.066 (4)	0.046 (4)	0.018 (4)	0.005 (3)
C304	0.093 (5)	0.064 (4)	0.081 (4)	0.039 (3)	0.020 (4)	−0.001 (3)
C305	0.064 (3)	0.056 (3)	0.048 (3)	0.027 (3)	0.005 (2)	−0.002 (2)
C306	0.061 (3)	0.075 (4)	0.065 (3)	0.023 (3)	0.032 (3)	0.008 (3)
C307	0.053 (3)	0.074 (4)	0.066 (3)	0.016 (3)	0.026 (3)	0.019 (3)
C308	0.041 (2)	0.052 (3)	0.046 (2)	0.009 (2)	0.012 (2)	0.009 (2)
C309	0.042 (2)	0.045 (3)	0.051 (3)	0.009 (2)	0.014 (2)	0.004 (2)
C310	0.051 (3)	0.044 (3)	0.051 (3)	0.013 (2)	0.013 (2)	0.004 (2)
C311	0.056 (3)	0.037 (3)	0.084 (4)	0.002 (2)	0.032 (3)	0.002 (2)
C312	0.051 (3)	0.051 (3)	0.072 (3)	0.004 (2)	0.025 (3)	0.004 (2)
C313	0.053 (3)	0.040 (2)	0.050 (3)	0.008 (2)	0.011 (2)	0.002 (2)
C314	0.045 (3)	0.049 (3)	0.050 (3)	0.000 (2)	0.008 (2)	0.012 (2)
C315	0.059 (3)	0.057 (3)	0.082 (4)	−0.002 (3)	0.015 (3)	0.016 (3)
C316	0.067 (4)	0.048 (3)	0.088 (4)	−0.003 (3)	0.006 (3)	0.021 (3)
C317	0.063 (3)	0.047 (3)	0.051 (3)	0.006 (2)	0.008 (2)	0.014 (2)
C318	0.089 (4)	0.052 (3)	0.051 (3)	0.016 (3)	0.015 (3)	0.008 (2)
C319	0.098 (4)	0.048 (3)	0.061 (3)	0.022 (3)	0.024 (3)	0.008 (2)
O320	0.178 (5)	0.054 (2)	0.062 (2)	0.052 (3)	0.008 (3)	−0.007 (2)
C321	0.080 (4)	0.052 (3)	0.064 (3)	0.011 (3)	0.018 (3)	0.009 (3)
O322	0.145 (5)	0.072 (3)	0.103 (4)	0.033 (3)	−0.015 (4)	−0.013 (3)
C323	0.078 (4)	0.043 (3)	0.075 (4)	0.011 (3)	0.016 (3)	−0.003 (2)
C324	0.152 (6)	0.044 (3)	0.062 (3)	0.020 (4)	0.020 (4)	0.001 (3)
C325	0.067 (3)	0.046 (3)	0.059 (3)	0.008 (2)	0.010 (3)	−0.006 (3)
O326	0.113 (3)	0.047 (2)	0.065 (2)	0.020 (2)	0.029 (2)	0.0045 (19)
O327	0.193 (6)	0.050 (2)	0.065 (3)	0.029 (3)	0.047 (3)	0.0053 (19)
C328	0.100 (5)	0.038 (3)	0.064 (3)	0.019 (3)	0.016 (3)	0.007 (2)
O329	0.155 (5)	0.055 (3)	0.108 (4)	0.007 (3)	0.029 (3)	−0.011 (2)
C330	0.120 (6)	0.076 (4)	0.123 (6)	0.040 (4)	0.056 (5)	0.007 (4)

Geometric parameters (Å, º)

C1—C2	1.537 (11)	C201—C202	1.525 (8)
C1—C10	1.562 (10)	C201—C210	1.545 (8)
C1—H1A	0.9700	C201—H20A	0.9700
C1—H1B	0.9700	C201—H20B	0.9700
C2—C3	1.484 (12)	C202—C203	1.497 (9)
C2—H2A	0.9700	C202—H20C	0.9700
C2—H2B	0.9700	C202—H20D	0.9700
C3—O20	1.463 (7)	C203—O220	1.465 (6)
C3—C4	1.513 (10)	C203—C204	1.507 (7)
C3—H3A	0.9800	C203—H20E	0.9800
C4—C5	1.525 (8)	C204—C205	1.522 (6)
C4—H4A	0.9700	C204—H20F	0.9700
C4—H4B	0.9700	C204—H20G	0.9700
C5—C6	1.299 (9)	C205—C206	1.327 (7)
C5—C10	1.497 (9)	C205—C210	1.514 (7)
C6—C7	1.483 (9)	C206—C207	1.483 (7)
C6—H6A	0.9300	C206—H20H	0.9300
C7—C8	1.506 (8)	C207—C208	1.520 (7)
C7—H7A	0.9700	C207—H20I	0.9700
C7—H7B	0.9700	C207—H20J	0.9700
C8—C14	1.520 (7)	C208—C214	1.509 (6)
C8—C9	1.529 (8)	C208—C209	1.526 (6)
C8—H8A	0.9800	C208—H20K	0.9800
C9—C11	1.527 (10)	C209—C211	1.549 (7)
C9—C10	1.553 (9)	C209—C210	1.567 (6)
C9—H9A	0.9800	C209—H20L	0.9800
C10—C19	1.565 (11)	C210—C219	1.536 (8)
C11—C12	1.574 (13)	C211—C212	1.552 (7)
C11—H11A	0.9700	C211—H21A	0.9700
C11—H11B	0.9700	C211—H21B	0.9700
C12—C13	1.520 (10)	C212—C213	1.529 (8)
C12—H12A	0.9700	C212—H21C	0.9700
C12—H12B	0.9700	C212—H21D	0.9700
C13—C14	1.514 (8)	C213—C218	1.510 (8)
C13—C17	1.541 (10)	C213—C214	1.540 (6)
C13—C18	1.579 (14)	C213—C217	1.559 (7)
C14—C15	1.519 (8)	C214—C215	1.524 (7)
C14—H14A	0.9800	C214—H21E	0.9800
C15—C16	1.535 (9)	C215—C216	1.543 (8)
C15—H15A	0.9700	C215—H21F	0.9700
C15—H15B	0.9700	C215—H21G	0.9700
C16—C17	1.540 (10)	C216—C217	1.522 (8)
C16—H16A	0.9700	C216—H21H	0.9700
C16—H16B	0.9700	C216—H21I	0.9700
C17—C28	1.456 (11)	C217—C228	1.503 (9)
C17—H17A	0.9800	C217—H21J	0.9800
C18—H18A	0.9600	C218—H21K	0.9600
C18—H18B	0.9600	C218—H21L	0.9600
C18—H18C	0.9600	C218—H21M	0.9600
C19—H19A	0.9600	C219—H21N	0.9600
C19—H19B	0.9600	C219—H21O	0.9600
C19—H19C	0.9600	C219—H21P	0.9600
O20—C21	1.316 (8)	O220—C221	1.332 (7)
C21—O22	1.150 (8)	C221—O222	1.190 (7)
C21—C23	1.470 (8)	C221—C223	1.509 (7)
C23—C24	1.498 (8)	C223—C224	1.454 (9)
C23—H23A	0.9700	C223—H22A	0.9700
C23—H23B	0.9700	C223—H22B	0.9700
C24—C25	1.462 (8)	C224—C225	1.488 (8)
C24—H24A	0.9700	C224—H22C	0.9700
C24—H24B	0.9700	C224—H22D	0.9700
C25—O26	1.197 (7)	C225—O226	1.193 (7)
C25—O27	1.282 (7)	C225—O227	1.275 (7)
O27—H27	0.8873	O227—H227	0.9382
C28—O29	1.356 (14)	C228—O229	1.164 (10)
C28—C30	1.369 (15)	C228—C230	1.524 (12)
C30—H30A	0.9600	C230—H23C	0.9600
C30—H30B	0.9600	C230—H23D	0.9600
C30—H30C	0.9600	C230—H23E	0.9600
C101—C102	1.519 (7)	C301—C310	1.531 (7)
C101—C110	1.537 (7)	C301—C302	1.532 (8)
C101—H10A	0.9700	C301—H30D	0.9700
C101—H10B	0.9700	C301—H30E	0.9700
C102—C103	1.493 (8)	C302—C303	1.478 (10)
C102—H10C	0.9700	C302—H30F	0.9700
C102—H10D	0.9700	C302—H30G	0.9700
C103—O120	1.464 (6)	C303—O320	1.470 (6)
C103—C104	1.516 (9)	C303—C304	1.518 (10)
C103—H10E	0.9800	C303—H30H	0.9800
C104—C105	1.515 (7)	C304—C305	1.517 (7)
C104—H10F	0.9700	C304—H30I	0.9700
C104—H10G	0.9700	C304—H30J	0.9700
C105—C106	1.290 (8)	C305—C306	1.322 (8)
C105—C110	1.533 (8)	C305—C310	1.522 (7)
C106—C107	1.504 (9)	C306—C307	1.462 (8)
C106—H10H	0.9300	C306—H30K	0.9300
C107—C108	1.538 (9)	C307—C308	1.533 (7)
C107—H10I	0.9700	C307—H30L	0.9700
C107—H10J	0.9700	C307—H30M	0.9700
C108—C114	1.524 (7)	C308—C314	1.519 (7)
C108—C109	1.537 (7)	C308—C309	1.539 (7)
C108—H10K	0.9800	C308—H30N	0.9800
C109—C111	1.541 (7)	C309—C311	1.535 (7)
C109—C110	1.545 (7)	C309—C310	1.537 (6)
C109—H10L	0.9800	C309—H30O	0.9800
C110—C119	1.527 (8)	C310—C319	1.548 (7)
C111—C112	1.519 (7)	C311—C312	1.524 (7)
C111—H11C	0.9700	C311—H31A	0.9700
C111—H11D	0.9700	C311—H31B	0.9700
C112—C113	1.515 (7)	C312—C313	1.515 (7)
C112—H11E	0.9700	C312—H31C	0.9700
C112—H11F	0.9700	C312—H31D	0.9700
C113—C118	1.512 (8)	C313—C314	1.522 (7)
C113—C114	1.529 (8)	C313—C318	1.532 (7)
C113—C117	1.554 (7)	C313—C317	1.576 (7)
C114—C115	1.544 (8)	C314—C315	1.538 (7)
C114—H11G	0.9800	C314—H31E	0.9800
C115—C116	1.544 (10)	C315—C316	1.529 (8)
C115—H11H	0.9700	C315—H31F	0.9700
C115—H11I	0.9700	C315—H31G	0.9700
C116—C117	1.539 (9)	C316—C317	1.521 (8)
C116—H11J	0.9700	C316—H31H	0.9700
C116—H11K	0.9700	C316—H31I	0.9700
C117—C128	1.533 (8)	C317—C328	1.506 (8)
C117—H11L	0.9800	C317—H31J	0.9800
C118—H11M	0.9600	C318—H31K	0.9600
C118—H11N	0.9600	C318—H31L	0.9600
C118—H11O	0.9600	C318—H31M	0.9600
C119—H11P	0.9600	C319—H31N	0.9600
C119—H11Q	0.9600	C319—H31O	0.9600
C119—H11R	0.9600	C319—H31P	0.9600
O120—C121	1.281 (8)	O320—C321	1.281 (7)
C121—O122	1.233 (9)	C321—O322	1.210 (7)
C121—C123	1.478 (8)	C321—C323	1.464 (8)
C123—C124	1.472 (9)	C323—C324	1.476 (8)
C123—H12C	0.9700	C323—H32A	0.9700
C123—H12D	0.9700	C323—H32B	0.9700
C124—C125	1.492 (8)	C324—C325	1.486 (8)
C124—H12E	0.9700	C324—H32C	0.9700
C124—H12F	0.9700	C324—H32D	0.9700
C125—O126	1.201 (7)	C325—O326	1.197 (7)
C125—O127	1.299 (7)	C325—O327	1.307 (7)
O127—H127	0.8727	O327—H327	1.0366
C128—O129	1.203 (7)	C328—O329	1.208 (7)
C128—C130	1.461 (9)	C328—C330	1.478 (11)
C130—H13A	0.9600	C330—H33A	0.9600
C130—H13B	0.9600	C330—H33B	0.9600
C130—H13C	0.9600	C330—H33C	0.9600
C2—C1—C10	114.1 (7)	C202—C201—C210	115.2 (5)
C2—C1—H1A	108.7	C202—C201—H20A	108.5
C10—C1—H1A	108.7	C210—C201—H20A	108.5
C2—C1—H1B	108.7	C202—C201—H20B	108.5
C10—C1—H1B	108.7	C210—C201—H20B	108.5
H1A—C1—H1B	107.6	H20A—C201—H20B	107.5
C3—C2—C1	109.4 (8)	C203—C202—C201	109.4 (5)
C3—C2—H2A	109.8	C203—C202—H20C	109.8
C1—C2—H2A	109.8	C201—C202—H20C	109.8
C3—C2—H2B	109.8	C203—C202—H20D	109.8
C1—C2—H2B	109.8	C201—C202—H20D	109.8
H2A—C2—H2B	108.2	H20C—C202—H20D	108.2
O20—C3—C2	106.8 (6)	O220—C203—C202	107.7 (4)
O20—C3—C4	108.1 (5)	O220—C203—C204	110.0 (4)
C2—C3—C4	110.7 (6)	C202—C203—C204	110.8 (5)
O20—C3—H3A	110.4	O220—C203—H20E	109.4
C2—C3—H3A	110.4	C202—C203—H20E	109.4
C4—C3—H3A	110.4	C204—C203—H20E	109.4
C3—C4—C5	110.2 (5)	C203—C204—C205	109.2 (4)
C3—C4—H4A	109.6	C203—C204—H20F	109.8
C5—C4—H4A	109.6	C205—C204—H20F	109.8
C3—C4—H4B	109.6	C203—C204—H20G	109.8
C5—C4—H4B	109.6	C205—C204—H20G	109.8
H4A—C4—H4B	108.1	H20F—C204—H20G	108.3
C6—C5—C10	122.4 (6)	C206—C205—C210	123.9 (4)
C6—C5—C4	120.7 (6)	C206—C205—C204	120.0 (5)
C10—C5—C4	116.9 (6)	C210—C205—C204	116.0 (4)
C5—C6—C7	126.1 (6)	C205—C206—C207	124.6 (5)
C5—C6—H6A	116.9	C205—C206—H20H	117.7
C7—C6—H6A	116.9	C207—C206—H20H	117.7
C6—C7—C8	113.2 (5)	C206—C207—C208	113.1 (4)
C6—C7—H7A	108.9	C206—C207—H20I	109.0
C8—C7—H7A	108.9	C208—C207—H20I	109.0
C6—C7—H7B	108.9	C206—C207—H20J	109.0
C8—C7—H7B	108.9	C208—C207—H20J	109.0
H7A—C7—H7B	107.8	H20I—C207—H20J	107.8
C7—C8—C14	111.8 (4)	C214—C208—C207	110.3 (4)
C7—C8—C9	109.1 (5)	C214—C208—C209	109.7 (4)
C14—C8—C9	110.4 (4)	C207—C208—C209	109.5 (4)
C7—C8—H8A	108.5	C214—C208—H20K	109.1
C14—C8—H8A	108.5	C207—C208—H20K	109.1
C9—C8—H8A	108.5	C209—C208—H20K	109.1
C11—C9—C8	112.5 (5)	C208—C209—C211	112.7 (4)
C11—C9—C10	112.9 (6)	C208—C209—C210	113.3 (4)
C8—C9—C10	112.3 (5)	C211—C209—C210	112.5 (4)
C11—C9—H9A	106.1	C208—C209—H20L	105.8
C8—C9—H9A	106.1	C211—C209—H20L	105.8
C10—C9—H9A	106.1	C210—C209—H20L	105.8
C5—C10—C9	110.3 (5)	C205—C210—C219	109.3 (5)
C5—C10—C1	109.3 (6)	C205—C210—C201	107.4 (4)
C9—C10—C1	107.4 (6)	C219—C210—C201	111.5 (5)
C5—C10—C19	106.2 (6)	C205—C210—C209	109.7 (4)
C9—C10—C19	113.9 (6)	C219—C210—C209	111.1 (4)
C1—C10—C19	109.7 (8)	C201—C210—C209	107.7 (4)
C9—C11—C12	111.7 (8)	C209—C211—C212	112.6 (4)
C9—C11—H11A	109.3	C209—C211—H21A	109.1
C12—C11—H11A	109.3	C212—C211—H21A	109.1
C9—C11—H11B	109.3	C209—C211—H21B	109.1
C12—C11—H11B	109.3	C212—C211—H21B	109.1
H11A—C11—H11B	107.9	H21A—C211—H21B	107.8
C13—C12—C11	109.2 (8)	C213—C212—C211	112.0 (4)
C13—C12—H12A	109.9	C213—C212—H21C	109.2
C11—C12—H12A	109.8	C211—C212—H21C	109.2
C13—C12—H12B	109.8	C213—C212—H21D	109.2
C11—C12—H12B	109.8	C211—C212—H21D	109.2
H12A—C12—H12B	108.3	H21C—C212—H21D	107.9
C14—C13—C12	106.9 (6)	C218—C213—C212	111.1 (5)
C14—C13—C17	100.4 (5)	C218—C213—C214	112.9 (4)
C12—C13—C17	114.3 (7)	C212—C213—C214	106.6 (4)
C14—C13—C18	110.5 (6)	C218—C213—C217	109.8 (4)
C12—C13—C18	114.0 (8)	C212—C213—C217	116.4 (4)
C17—C13—C18	109.8 (6)	C214—C213—C217	99.6 (4)
C13—C14—C15	104.1 (5)	C208—C214—C215	119.6 (4)
C13—C14—C8	115.1 (5)	C208—C214—C213	115.2 (3)
C15—C14—C8	120.2 (4)	C215—C214—C213	104.5 (4)
C13—C14—H14A	105.4	C208—C214—H21E	105.5
C15—C14—H14A	105.4	C215—C214—H21E	105.5
C8—C14—H14A	105.4	C213—C214—H21E	105.5
C14—C15—C16	104.7 (5)	C214—C215—C216	103.7 (4)
C14—C15—H15A	110.8	C214—C215—H21F	111.0
C16—C15—H15A	110.8	C216—C215—H21F	111.0
C14—C15—H15B	110.8	C214—C215—H21G	111.0
C16—C15—H15B	110.8	C216—C215—H21G	111.0
H15A—C15—H15B	108.9	H21F—C215—H21G	109.0
C15—C16—C17	105.9 (5)	C217—C216—C215	107.2 (4)
C15—C16—H16A	110.6	C217—C216—H21H	110.3
C17—C16—H16A	110.6	C215—C216—H21H	110.3
C15—C16—H16B	110.6	C217—C216—H21I	110.3
C17—C16—H16B	110.6	C215—C216—H21I	110.3
H16A—C16—H16B	108.7	H21H—C216—H21I	108.5
C28—C17—C16	116.6 (6)	C228—C217—C216	113.4 (5)
C28—C17—C13	119.9 (8)	C228—C217—C213	116.2 (4)
C16—C17—C13	103.4 (5)	C216—C217—C213	104.9 (4)
C28—C17—H17A	105.2	C228—C217—H21J	107.3
C16—C17—H17A	105.2	C216—C217—H21J	107.3
C13—C17—H17A	105.2	C213—C217—H21J	107.3
C13—C18—H18A	109.5	C213—C218—H21K	109.5
C13—C18—H18B	109.5	C213—C218—H21L	109.5
H18A—C18—H18B	109.5	H21K—C218—H21L	109.5
C13—C18—H18C	109.5	C213—C218—H21M	109.5
H18A—C18—H18C	109.5	H21K—C218—H21M	109.5
H18B—C18—H18C	109.5	H21L—C218—H21M	109.5
C10—C19—H19A	109.5	C210—C219—H21N	109.5
C10—C19—H19B	109.5	C210—C219—H21O	109.5
H19A—C19—H19B	109.5	H21N—C219—H21O	109.5
C10—C19—H19C	109.5	C210—C219—H21P	109.5
H19A—C19—H19C	109.5	H21N—C219—H21P	109.5
H19B—C19—H19C	109.5	H21O—C219—H21P	109.5
C21—O20—C3	117.4 (5)	C221—O220—C203	117.3 (4)
O22—C21—O20	121.9 (6)	O222—C221—O220	124.9 (5)
O22—C21—C23	125.3 (6)	O222—C221—C223	124.1 (5)
O20—C21—C23	112.9 (5)	O220—C221—C223	111.0 (5)
C21—C23—C24	112.6 (5)	C224—C223—C221	113.7 (5)
C21—C23—H23A	109.1	C224—C223—H22A	108.8
C24—C23—H23A	109.1	C221—C223—H22A	108.8
C21—C23—H23B	109.1	C224—C223—H22B	108.8
C24—C23—H23B	109.1	C221—C223—H22B	108.8
H23A—C23—H23B	107.8	H22A—C223—H22B	107.7
C25—C24—C23	116.4 (5)	C223—C224—C225	113.6 (5)
C25—C24—H24A	108.2	C223—C224—H22C	108.8
C23—C24—H24A	108.2	C225—C224—H22C	108.8
C25—C24—H24B	108.2	C223—C224—H22D	108.8
C23—C24—H24B	108.2	C225—C224—H22D	108.8
H24A—C24—H24B	107.3	H22C—C224—H22D	107.7
O26—C25—O27	121.5 (5)	O226—C225—O227	121.9 (5)
O26—C25—C24	124.8 (6)	O226—C225—C224	123.2 (5)
O27—C25—C24	113.6 (5)	O227—C225—C224	114.9 (5)
C25—O27—H27	124.5	C225—O227—H227	122.5
O29—C28—C30	116.6 (9)	O229—C228—C217	122.3 (7)
O29—C28—C17	128.2 (9)	O229—C228—C230	122.5 (8)
C30—C28—C17	110.3 (10)	C217—C228—C230	115.2 (8)
C28—C30—H30A	109.5	C228—C230—H23C	109.5
C28—C30—H30B	109.5	C228—C230—H23D	109.5
H30A—C30—H30B	109.5	H23C—C230—H23D	109.5
C28—C30—H30C	109.5	C228—C230—H23E	109.5
H30A—C30—H30C	109.5	H23C—C230—H23E	109.5
H30B—C30—H30C	109.5	H23D—C230—H23E	109.5
C102—C101—C110	114.6 (5)	C310—C301—C302	114.8 (5)
C102—C101—H10A	108.6	C310—C301—H30D	108.6
C110—C101—H10A	108.6	C302—C301—H30D	108.6
C102—C101—H10B	108.6	C310—C301—H30E	108.6
C110—C101—H10B	108.6	C302—C301—H30E	108.6
H10A—C101—H10B	107.6	H30D—C301—H30E	107.5
C103—C102—C101	109.8 (4)	C303—C302—C301	111.2 (5)
C103—C102—H10C	109.7	C303—C302—H30F	109.4
C101—C102—H10C	109.7	C301—C302—H30F	109.4
C103—C102—H10D	109.7	C303—C302—H30G	109.4
C101—C102—H10D	109.7	C301—C302—H30G	109.4
H10C—C102—H10D	108.2	H30F—C302—H30G	108.0
O120—C103—C102	110.7 (4)	O320—C303—C302	111.2 (6)
O120—C103—C104	106.7 (5)	O320—C303—C304	104.9 (5)
C102—C103—C104	111.9 (5)	C302—C303—C304	110.5 (5)
O120—C103—H10E	109.1	O320—C303—H30H	110.0
C102—C103—H10E	109.1	C302—C303—H30H	110.0
C104—C103—H10E	109.1	C304—C303—H30H	110.0
C105—C104—C103	111.0 (5)	C305—C304—C303	110.3 (5)
C105—C104—H10F	109.4	C305—C304—H30I	109.6
C103—C104—H10F	109.4	C303—C304—H30I	109.6
C105—C104—H10G	109.4	C305—C304—H30J	109.6
C103—C104—H10G	109.4	C303—C304—H30J	109.6
H10F—C104—H10G	108.0	H30I—C304—H30J	108.1
C106—C105—C104	121.2 (5)	C306—C305—C304	119.5 (5)
C106—C105—C110	121.7 (5)	C306—C305—C310	123.2 (5)
C104—C105—C110	117.1 (4)	C304—C305—C310	117.2 (5)
C105—C106—C107	127.6 (6)	C305—C306—C307	125.6 (5)
C105—C106—H10H	116.2	C305—C306—H30K	117.2
C107—C106—H10H	116.2	C307—C306—H30K	117.2
C106—C107—C108	111.7 (5)	C306—C307—C308	113.7 (4)
C106—C107—H10I	109.3	C306—C307—H30L	108.8
C108—C107—H10I	109.3	C308—C307—H30L	108.8
C106—C107—H10J	109.3	C306—C307—H30M	108.8
C108—C107—H10J	109.3	C308—C307—H30M	108.8
H10I—C107—H10J	107.9	H30L—C307—H30M	107.7
C114—C108—C109	109.7 (4)	C314—C308—C307	111.1 (4)
C114—C108—C107	110.2 (5)	C314—C308—C309	109.5 (4)
C109—C108—C107	108.8 (5)	C307—C308—C309	109.8 (4)
C114—C108—H10K	109.4	C314—C308—H30N	108.8
C109—C108—H10K	109.4	C307—C308—H30N	108.8
C107—C108—H10K	109.4	C309—C308—H30N	108.8
C108—C109—C111	111.7 (4)	C311—C309—C310	113.7 (4)
C108—C109—C110	113.0 (4)	C311—C309—C308	111.6 (4)
C111—C109—C110	114.4 (4)	C310—C309—C308	113.1 (4)
C108—C109—H10L	105.6	C311—C309—H30O	105.9
C111—C109—H10L	105.6	C310—C309—H30O	105.9
C110—C109—H10L	105.6	C308—C309—H30O	105.9
C119—C110—C105	109.0 (5)	C305—C310—C301	109.5 (4)
C119—C110—C101	108.6 (5)	C305—C310—C309	109.2 (4)
C105—C110—C101	109.5 (4)	C301—C310—C309	109.0 (4)
C119—C110—C109	111.1 (4)	C305—C310—C319	107.8 (4)
C105—C110—C109	109.7 (4)	C301—C310—C319	108.8 (5)
C101—C110—C109	108.9 (4)	C309—C310—C319	112.6 (4)
C112—C111—C109	114.3 (4)	C312—C311—C309	114.1 (4)
C112—C111—H11C	108.7	C312—C311—H31A	108.7
C109—C111—H11C	108.7	C309—C311—H31A	108.7
C112—C111—H11D	108.7	C312—C311—H31B	108.7
C109—C111—H11D	108.7	C309—C311—H31B	108.7
H11C—C111—H11D	107.6	H31A—C311—H31B	107.6
C113—C112—C111	111.4 (4)	C313—C312—C311	111.6 (4)
C113—C112—H11E	109.3	C313—C312—H31C	109.3
C111—C112—H11E	109.3	C311—C312—H31C	109.3
C113—C112—H11F	109.3	C313—C312—H31D	109.3
C111—C112—H11F	109.3	C311—C312—H31D	109.3
H11E—C112—H11F	108.0	H31C—C312—H31D	108.0
C118—C113—C112	110.9 (5)	C312—C313—C314	108.2 (4)
C118—C113—C114	114.0 (5)	C312—C313—C318	110.2 (4)
C112—C113—C114	106.3 (4)	C314—C313—C318	112.9 (4)
C118—C113—C117	110.3 (4)	C312—C313—C317	117.2 (4)
C112—C113—C117	116.2 (4)	C314—C313—C317	99.0 (4)
C114—C113—C117	98.7 (4)	C318—C313—C317	109.1 (4)
C108—C114—C113	115.1 (4)	C308—C314—C313	115.6 (4)
C108—C114—C115	117.8 (5)	C308—C314—C315	119.0 (4)
C113—C114—C115	104.4 (5)	C313—C314—C315	104.5 (4)
C108—C114—H11G	106.2	C308—C314—H31E	105.5
C113—C114—H11G	106.2	C313—C314—H31E	105.5
C115—C114—H11G	106.2	C315—C314—H31E	105.5
C116—C115—C114	103.2 (5)	C316—C315—C314	103.3 (4)
C116—C115—H11H	111.1	C316—C315—H31F	111.1
C114—C115—H11H	111.1	C314—C315—H31F	111.1
C116—C115—H11I	111.1	C316—C315—H31G	111.1
C114—C115—H11I	111.1	C314—C315—H31G	111.1
H11H—C115—H11I	109.1	H31F—C315—H31G	109.1
C117—C116—C115	106.5 (5)	C317—C316—C315	107.9 (4)
C117—C116—H11J	110.4	C317—C316—H31H	110.1
C115—C116—H11J	110.4	C315—C316—H31H	110.1
C117—C116—H11K	110.4	C317—C316—H31I	110.1
C115—C116—H11K	110.4	C315—C316—H31I	110.1
H11J—C116—H11K	108.6	H31H—C316—H31I	108.4
C128—C117—C116	112.6 (5)	C328—C317—C316	114.3 (5)
C128—C117—C113	115.7 (4)	C328—C317—C313	117.5 (4)
C116—C117—C113	104.1 (5)	C316—C317—C313	103.0 (4)
C128—C117—H11L	108.0	C328—C317—H31J	107.2
C116—C117—H11L	108.0	C316—C317—H31J	107.2
C113—C117—H11L	108.0	C313—C317—H31J	107.2
C113—C118—H11M	109.5	C313—C318—H31K	109.5
C113—C118—H11N	109.5	C313—C318—H31L	109.5
H11M—C118—H11N	109.5	H31K—C318—H31L	109.5
C113—C118—H11O	109.5	C313—C318—H31M	109.5
H11M—C118—H11O	109.5	H31K—C318—H31M	109.5
H11N—C118—H11O	109.5	H31L—C318—H31M	109.5
C110—C119—H11P	109.5	C310—C319—H31N	109.5
C110—C119—H11Q	109.5	C310—C319—H31O	109.5
H11P—C119—H11Q	109.5	H31N—C319—H31O	109.5
C110—C119—H11R	109.5	C310—C319—H31P	109.5
H11P—C119—H11R	109.5	H31N—C319—H31P	109.5
H11Q—C119—H11R	109.5	H31O—C319—H31P	109.5
C121—O120—C103	118.8 (5)	C321—O320—C303	120.1 (5)
O122—C121—O120	122.2 (6)	O322—C321—O320	120.9 (5)
O122—C121—C123	121.8 (7)	O322—C321—C323	123.4 (6)
O120—C121—C123	115.3 (6)	O320—C321—C323	115.3 (5)
C124—C123—C121	113.8 (5)	C321—C323—C324	114.9 (5)
C124—C123—H12C	108.8	C321—C323—H32A	108.6
C121—C123—H12C	108.8	C324—C323—H32A	108.6
C124—C123—H12D	108.8	C321—C323—H32B	108.6
C121—C123—H12D	108.8	C324—C323—H32B	108.6
H12C—C123—H12D	107.7	H32A—C323—H32B	107.5
C123—C124—C125	115.8 (5)	C323—C324—C325	116.3 (5)
C123—C124—H12E	108.3	C323—C324—H32C	108.2
C125—C124—H12E	108.3	C325—C324—H32C	108.2
C123—C124—H12F	108.3	C323—C324—H32D	108.2
C125—C124—H12F	108.3	C325—C324—H32D	108.2
H12E—C124—H12F	107.4	H32C—C324—H32D	107.4
O126—C125—O127	122.5 (5)	O326—C325—O327	122.2 (5)
O126—C125—C124	124.2 (5)	O326—C325—C324	124.4 (5)
O127—C125—C124	113.4 (5)	O327—C325—C324	113.4 (5)
C125—O127—H127	122.8	C325—O327—H327	114.9
O129—C128—C130	120.7 (6)	O329—C328—C330	119.6 (6)
O129—C128—C117	121.7 (6)	O329—C328—C317	120.7 (6)
C130—C128—C117	117.6 (5)	C330—C328—C317	119.6 (5)
C128—C130—H13A	109.5	C328—C330—H33A	109.5
C128—C130—H13B	109.5	C328—C330—H33B	109.5
H13A—C130—H13B	109.5	H33A—C330—H33B	109.5
C128—C130—H13C	109.5	C328—C330—H33C	109.5
H13A—C130—H13C	109.5	H33A—C330—H33C	109.5
H13B—C130—H13C	109.5	H33B—C330—H33C	109.5
C10—C1—C2—C3	−56.2 (13)	C210—C201—C202—C203	−55.7 (8)
C1—C2—C3—O20	178.6 (7)	C201—C202—C203—O220	179.6 (5)
C1—C2—C3—C4	61.1 (10)	C201—C202—C203—C204	59.3 (7)
O20—C3—C4—C5	−175.1 (5)	O220—C203—C204—C205	−178.1 (4)
C2—C3—C4—C5	−58.5 (8)	C202—C203—C204—C205	−59.2 (6)
C3—C4—C5—C6	−127.1 (7)	C203—C204—C205—C206	−121.3 (5)
C3—C4—C5—C10	52.1 (8)	C203—C204—C205—C210	56.2 (6)
C10—C5—C6—C7	1.0 (11)	C210—C205—C206—C207	2.6 (8)
C4—C5—C6—C7	−179.9 (6)	C204—C205—C206—C207	179.9 (5)
C5—C6—C7—C8	12.6 (10)	C205—C206—C207—C208	14.7 (8)
C6—C7—C8—C14	−163.9 (5)	C206—C207—C208—C214	−165.1 (4)
C6—C7—C8—C9	−41.6 (7)	C206—C207—C208—C209	−44.2 (6)
C7—C8—C9—C11	−171.4 (8)	C214—C208—C209—C211	−49.9 (5)
C14—C8—C9—C11	−48.2 (9)	C207—C208—C209—C211	−171.2 (5)
C7—C8—C9—C10	59.9 (7)	C214—C208—C209—C210	−179.2 (4)
C14—C8—C9—C10	−176.9 (5)	C207—C208—C209—C210	59.6 (5)
C6—C5—C10—C9	15.8 (9)	C206—C205—C210—C219	−111.2 (6)
C4—C5—C10—C9	−163.4 (5)	C204—C205—C210—C219	71.4 (6)
C6—C5—C10—C1	133.7 (8)	C206—C205—C210—C201	127.7 (5)
C4—C5—C10—C1	−45.5 (9)	C204—C205—C210—C201	−49.7 (6)
C6—C5—C10—C19	−108.1 (7)	C206—C205—C210—C209	10.9 (7)
C4—C5—C10—C19	72.8 (7)	C204—C205—C210—C209	−166.6 (4)
C11—C9—C10—C5	−174.7 (7)	C202—C201—C210—C205	49.3 (7)
C8—C9—C10—C5	−46.2 (7)	C202—C201—C210—C219	−70.5 (7)
C11—C9—C10—C1	66.2 (9)	C202—C201—C210—C209	167.4 (5)
C8—C9—C10—C1	−165.2 (7)	C208—C209—C210—C205	−41.9 (6)
C11—C9—C10—C19	−55.5 (9)	C211—C209—C210—C205	−171.3 (5)
C8—C9—C10—C19	73.1 (8)	C208—C209—C210—C219	79.0 (6)
C2—C1—C10—C5	47.1 (12)	C211—C209—C210—C219	−50.3 (6)
C2—C1—C10—C9	166.7 (8)	C208—C209—C210—C201	−158.6 (4)
C2—C1—C10—C19	−69.0 (11)	C211—C209—C210—C201	72.1 (6)
C8—C9—C11—C12	51.8 (11)	C208—C209—C211—C212	49.5 (7)
C10—C9—C11—C12	−179.8 (8)	C210—C209—C211—C212	179.1 (5)
C9—C11—C12—C13	−58.6 (13)	C209—C211—C212—C213	−53.7 (7)
C11—C12—C13—C14	60.6 (11)	C211—C212—C213—C218	−67.1 (6)
C11—C12—C13—C17	170.7 (8)	C211—C212—C213—C214	56.3 (6)
C11—C12—C13—C18	−61.9 (10)	C211—C212—C213—C217	166.3 (5)
C12—C13—C14—C15	165.2 (8)	C207—C208—C214—C215	−55.8 (6)
C17—C13—C14—C15	45.7 (7)	C209—C208—C214—C215	−176.6 (4)
C18—C13—C14—C15	−70.2 (6)	C207—C208—C214—C213	178.4 (4)
C12—C13—C14—C8	−61.2 (9)	C209—C208—C214—C213	57.7 (5)
C17—C13—C14—C8	179.3 (5)	C218—C213—C214—C208	61.8 (6)
C18—C13—C14—C8	63.5 (7)	C212—C213—C214—C208	−60.5 (5)
C7—C8—C14—C13	176.1 (6)	C217—C213—C214—C208	178.2 (4)
C9—C8—C14—C13	54.5 (7)	C218—C213—C214—C215	−71.4 (5)
C7—C8—C14—C15	−58.2 (7)	C212—C213—C214—C215	166.3 (4)
C9—C8—C14—C15	−179.8 (5)	C217—C213—C214—C215	45.0 (5)
C13—C14—C15—C16	−31.7 (7)	C208—C214—C215—C216	−165.4 (4)
C8—C14—C15—C16	−162.4 (5)	C213—C214—C215—C216	−34.8 (6)
C14—C15—C16—C17	4.9 (7)	C214—C215—C216—C217	10.1 (7)
C15—C16—C17—C28	156.9 (10)	C215—C216—C217—C228	145.5 (6)
C15—C16—C17—C13	23.0 (8)	C215—C216—C217—C213	17.7 (7)
C14—C13—C17—C28	−173.9 (9)	C218—C213—C217—C228	−45.3 (7)
C12—C13—C17—C28	72.1 (12)	C212—C213—C217—C228	82.0 (7)
C18—C13—C17—C28	−57.5 (10)	C214—C213—C217—C228	−164.0 (6)
C14—C13—C17—C16	−41.9 (7)	C218—C213—C217—C216	80.8 (6)
C12—C13—C17—C16	−155.9 (8)	C212—C213—C217—C216	−151.9 (5)
C18—C13—C17—C16	74.5 (7)	C214—C213—C217—C216	−37.9 (5)
C2—C3—O20—C21	138.1 (7)	C202—C203—O220—C221	158.5 (5)
C4—C3—O20—C21	−102.8 (7)	C204—C203—O220—C221	−80.7 (6)
C3—O20—C21—O22	−3.8 (12)	C203—O220—C221—O222	1.9 (8)
C3—O20—C21—C23	177.6 (6)	C203—O220—C221—C223	−179.0 (5)
O22—C21—C23—C24	−14.2 (12)	O222—C221—C223—C224	−34.3 (9)
O20—C21—C23—C24	164.4 (7)	O220—C221—C223—C224	146.6 (6)
C21—C23—C24—C25	−178.1 (6)	C221—C223—C224—C225	−177.4 (6)
C23—C24—C25—O26	−5.2 (12)	C223—C224—C225—O226	−28.4 (10)
C23—C24—C25—O27	173.0 (8)	C223—C224—C225—O227	150.1 (7)
C16—C17—C28—O29	−12 (2)	C216—C217—C228—O229	−11.4 (11)
C13—C17—C28—O29	113.6 (16)	C213—C217—C228—O229	110.2 (8)
C16—C17—C28—C30	141.5 (9)	C216—C217—C228—C230	167.7 (7)
C13—C17—C28—C30	−92.5 (13)	C213—C217—C228—C230	−70.7 (9)
C110—C101—C102—C103	−57.0 (7)	C310—C301—C302—C303	−54.7 (7)
C101—C102—C103—O120	178.3 (5)	C301—C302—C303—O320	175.5 (5)
C101—C102—C103—C104	59.4 (7)	C301—C302—C303—C304	59.4 (6)
O120—C103—C104—C105	−176.1 (5)	O320—C303—C304—C305	−177.0 (5)
C102—C103—C104—C105	−54.8 (7)	C302—C303—C304—C305	−57.0 (7)
C103—C104—C105—C106	−130.9 (7)	C303—C304—C305—C306	−129.8 (6)
C103—C104—C105—C110	48.0 (7)	C303—C304—C305—C310	51.0 (7)
C104—C105—C106—C107	−179.1 (8)	C304—C305—C306—C307	−178.3 (5)
C110—C105—C106—C107	2.0 (13)	C310—C305—C306—C307	0.9 (9)
C105—C106—C107—C108	11.5 (14)	C305—C306—C307—C308	10.4 (8)
C106—C107—C108—C114	−161.3 (7)	C306—C307—C308—C314	−159.8 (4)
C106—C107—C108—C109	−41.0 (9)	C306—C307—C308—C309	−38.6 (6)
C114—C108—C109—C111	−47.6 (6)	C314—C308—C309—C311	−49.4 (5)
C107—C108—C109—C111	−168.1 (5)	C307—C308—C309—C311	−171.6 (4)
C114—C108—C109—C110	−178.3 (4)	C314—C308—C309—C310	−179.1 (4)
C107—C108—C109—C110	61.2 (6)	C307—C308—C309—C310	58.7 (5)
C106—C105—C110—C119	−106.4 (7)	C306—C305—C310—C301	136.5 (5)
C104—C105—C110—C119	74.8 (6)	C304—C305—C310—C301	−44.3 (6)
C106—C105—C110—C101	135.0 (7)	C306—C305—C310—C309	17.3 (7)
C104—C105—C110—C101	−43.9 (7)	C304—C305—C310—C309	−163.6 (4)
C106—C105—C110—C109	15.5 (8)	C306—C305—C310—C319	−105.3 (6)
C104—C105—C110—C109	−163.3 (5)	C304—C305—C310—C319	73.8 (6)
C102—C101—C110—C119	−71.0 (6)	C302—C301—C310—C305	44.9 (7)
C102—C101—C110—C105	47.9 (6)	C302—C301—C310—C309	164.3 (5)
C102—C101—C110—C109	167.9 (4)	C302—C301—C310—C319	−72.6 (6)
C108—C109—C110—C119	73.3 (6)	C311—C309—C310—C305	−175.4 (4)
C111—C109—C110—C119	−56.0 (6)	C308—C309—C310—C305	−46.8 (5)
C108—C109—C110—C105	−47.3 (6)	C311—C309—C310—C301	65.0 (5)
C111—C109—C110—C105	−176.6 (5)	C308—C309—C310—C301	−166.4 (4)
C108—C109—C110—C101	−167.2 (5)	C311—C309—C310—C319	−55.7 (6)
C111—C109—C110—C101	63.5 (6)	C308—C309—C310—C319	72.8 (5)
C108—C109—C111—C112	49.1 (6)	C310—C309—C311—C312	−179.7 (4)
C110—C109—C111—C112	179.1 (4)	C308—C309—C311—C312	50.9 (6)
C109—C111—C112—C113	−55.4 (6)	C309—C311—C312—C313	−54.2 (6)
C111—C112—C113—C118	−66.5 (6)	C311—C312—C313—C314	54.7 (5)
C111—C112—C113—C114	57.9 (6)	C311—C312—C313—C318	−69.1 (5)
C111—C112—C113—C117	166.5 (4)	C311—C312—C313—C317	165.4 (4)
C109—C108—C114—C113	56.7 (6)	C307—C308—C314—C313	177.0 (4)
C107—C108—C114—C113	176.4 (6)	C309—C308—C314—C313	55.6 (5)
C109—C108—C114—C115	−179.5 (6)	C307—C308—C314—C315	−57.2 (6)
C107—C108—C114—C115	−59.7 (9)	C309—C308—C314—C315	−178.6 (4)
C118—C113—C114—C108	61.3 (6)	C312—C313—C314—C308	−58.1 (5)
C112—C113—C114—C108	−61.2 (6)	C318—C313—C314—C308	64.1 (5)
C117—C113—C114—C108	178.2 (5)	C317—C313—C314—C308	179.3 (4)
C118—C113—C114—C115	−69.4 (6)	C312—C313—C314—C315	169.1 (4)
C112—C113—C114—C115	168.1 (5)	C318—C313—C314—C315	−68.7 (5)
C117—C113—C114—C115	47.5 (6)	C317—C313—C314—C315	46.5 (4)
C108—C114—C115—C116	−163.3 (6)	C308—C314—C315—C316	−164.2 (4)
C113—C114—C115—C116	−34.3 (8)	C313—C314—C315—C316	−33.3 (5)
C114—C115—C116—C117	6.7 (9)	C314—C315—C316—C317	5.7 (6)
C115—C116—C117—C128	148.7 (7)	C315—C316—C317—C328	151.2 (5)
C115—C116—C117—C113	22.6 (8)	C315—C316—C317—C313	22.7 (6)
C118—C113—C117—C128	−46.9 (7)	C312—C313—C317—C328	75.7 (6)
C112—C113—C117—C128	80.4 (6)	C314—C313—C317—C328	−168.4 (5)
C114—C113—C117—C128	−166.6 (5)	C318—C313—C317—C328	−50.3 (6)
C118—C113—C117—C116	77.2 (6)	C312—C313—C317—C316	−157.7 (5)
C112—C113—C117—C116	−155.5 (6)	C314—C313—C317—C316	−41.9 (5)
C114—C113—C117—C116	−42.5 (6)	C318—C313—C317—C316	76.2 (5)
C102—C103—O120—C121	82.8 (7)	C302—C303—O320—C321	95.0 (7)
C104—C103—O120—C121	−155.2 (6)	C304—C303—O320—C321	−145.5 (6)
C103—O120—C121—O122	−10.5 (11)	C303—O320—C321—O322	−5.0 (11)
C103—O120—C121—C123	179.0 (5)	C303—O320—C321—C323	−177.8 (6)
O122—C121—C123—C124	30.4 (11)	O322—C321—C323—C324	36.2 (10)
O120—C121—C123—C124	−159.0 (7)	O320—C321—C323—C324	−151.2 (7)
C121—C123—C124—C125	−178.3 (7)	C321—C323—C324—C325	−175.3 (6)
C123—C124—C125—O126	11.6 (11)	C323—C324—C325—O326	11.9 (10)
C123—C124—C125—O127	−170.1 (7)	C323—C324—C325—O327	−168.3 (7)
C116—C117—C128—O129	−5.2 (10)	C316—C317—C328—O329	1.3 (8)
C113—C117—C128—O129	114.3 (7)	C313—C317—C328—O329	122.1 (6)
C116—C117—C128—C130	174.5 (6)	C316—C317—C328—C330	178.0 (6)
C113—C117—C128—C130	−65.9 (7)	C313—C317—C328—C330	−61.2 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O27—H27···O226^i	0.89	1.77	2.635 (7)	164
O127—H127···O326^ii	0.87	1.83	2.689 (6)	167
O227—H227···O26^iii	0.94	1.77	2.683 (6)	165
O327—H327···O126^iv	1.04	1.67	2.707 (5)	174

Symmetry codes: (i) x, y−2, z; (ii) x, y+2, z+1; (iii) x, y+2, z; (iv) x, y−2, z−1.