(3S*,16S*,20R*,22R*,24S*)-3,22,25-Trihydr­oxy-16,24:20,24-diepoxy­cholest-5-en-3-yl acetate methanol solvate

Zhang, W.; Yao, G.-M.; Guo, Y.-W.

doi:10.1107/S160053680502489X

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(3S,16S,20R,22R,24S*)-3,22,25-Trihydroxy-16,24:20,24-diepoxycholest-5-en-3-yl acetate methanol solvate

W. Zhang, G.-M. Yao and Y.-W. Guo

The title compound, C₂₉H₄₄O₆·CH₄O, namely suberoretisteroid A methanol solvate, is a fused hexacyclic steroid which was isolated from the South China Sea gorgonian Suberogorgia reticulata. There are two independent molecules in the asymmetric unit. Suberoretisteroid A molecules and methanol solvent molecules are linked via intermolecular O—H

O hydrogen bonds to form two independent two-dimensional frameworks.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502489X/lh6462sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680502489X/lh6462Isup2.hkl Contains datablock I

CCDC reference: 238944

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.013 Å
R factor = 0.071
wR factor = 0.173
Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         36 Perc.
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         13

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.738     0.980
            Tmin(prime) and Tmax expected:      0.965     0.984
            RR(prime) =      0.767
            Please check that your absorption correction is appropriate.
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.769
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.150
SHFSU01_ALERT_2_C  The absolute value of parameter shift to su ratio > 0.05
            Absolute value of the parameter shift to su ratio given   0.090
            Additional refinement cycles may be required.
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.15
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.77
PLAT080_ALERT_2_C Maximum Shift/Error ............................       0.09
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT213_ALERT_2_C Atom C44     has ADP max/min Ratio .............       3.70 prolat
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C19     ..       5.35 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C28
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C39
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C54
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.18
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.18
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      42.00 A   3  

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           25.50
           From the CIF: _reflns_number_total               5608
           Count of symmetry unique reflns         5649
           Completeness (_total/calc)             99.27%
           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
   2 ALERT level B = Potentially serious problem
  19 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

(3S*,16S*,20R*,22R*,24S*)-3,22,25-Trihydroxy-16,24:20,24-diepoxycholest- 5-en-3-yl acetate methanol solvate top

Crystal data top

C₂₉H₄₄O₆·CH₄O	F(000) = 1136
M_r = 520.68	D_x = 1.171 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 946 reflections
a = 8.6596 (17) Å	θ = 4.9–33.2°
b = 22.247 (4) Å	µ = 0.08 mm⁻¹
c = 15.891 (3) Å	T = 293 K
β = 105.314 (3)°	Block, colorless
V = 2952.7 (10) Å³	0.42 × 0.21 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	5608 independent reflections
Radiation source: fine-focus sealed tube	2037 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.150
φ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.738, T_max = 0.980	k = −26→26
15224 measured reflections	l = −19→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 0.77	w = 1/[σ²(F_o²) + (0.0481P)²] where P = (F_o² + 2F_c²)/3
5608 reflections	(Δ/σ)_max = 0.090
688 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.4001 (7)	0.5089 (3)	0.0273 (4)	0.0554 (18)
O2	−0.3176 (9)	0.4521 (4)	−0.0679 (4)	0.075 (2)
O3	0.7014 (7)	0.4619 (3)	0.5906 (4)	0.0519 (18)
O4	0.5882 (7)	0.4443 (3)	0.7048 (3)	0.0497 (17)
O5	0.6271 (11)	0.2942 (3)	0.6367 (5)	0.081 (2)
H5	0.5887	0.2657	0.6569	0.121*
O6	0.8714 (9)	0.4800 (4)	0.8229 (4)	0.076 (2)
H6	0.8191	0.4505	0.8296	0.115*
O7	−0.1029 (7)	0.2022 (3)	0.6421 (3)	0.0514 (18)
O8	0.0906 (9)	0.2554 (4)	0.7336 (4)	0.090 (3)
O9	0.4458 (7)	0.2556 (3)	0.0763 (3)	0.0472 (17)
O10	0.2228 (7)	0.2713 (3)	−0.0382 (3)	0.0428 (15)
O11	0.3244 (9)	0.4226 (3)	0.0287 (4)	0.067 (2)
H11	0.2892	0.4536	0.0026	0.100*
O12	0.3941 (8)	0.2373 (4)	−0.1555 (3)	0.069 (2)
H12	0.3468	0.2696	−0.1613	0.103*
O13	0.5034 (11)	0.1997 (4)	0.7086 (5)	0.089 (3)
H13	0.5430	0.2085	0.7599	0.133*
O14	0.1163 (10)	0.5136 (3)	0.9556 (4)	0.078 (2)
H14A	0.0845	0.5059	0.9035	0.117*
C1	−0.2224 (11)	0.4545 (5)	0.2549 (5)	0.052 (3)
H1A	−0.2672	0.4523	0.3047	0.063*
H1B	−0.1993	0.4138	0.2401	0.063*
C2	−0.3510 (11)	0.4821 (5)	0.1761 (5)	0.054 (3)
H2A	−0.4484	0.4584	0.1637	0.064*
H2B	−0.3764	0.5229	0.1893	0.064*
C3	−0.2811 (11)	0.4816 (5)	0.0990 (5)	0.048 (3)
H3	−0.2594	0.4402	0.0842	0.058*
C4	−0.1310 (11)	0.5185 (4)	0.1163 (5)	0.046 (2)
H4A	−0.1580	0.5604	0.1217	0.055*
H4B	−0.0860	0.5151	0.0667	0.055*
C5	−0.0062 (12)	0.4998 (4)	0.1975 (6)	0.048 (3)
C6	0.1429 (12)	0.4882 (4)	0.1972 (5)	0.051 (3)
H6A	0.1673	0.4911	0.1437	0.061*
C7	0.2726 (11)	0.4716 (5)	0.2717 (5)	0.054 (3)
H7A	0.3646	0.4966	0.2721	0.065*
H7B	0.3023	0.4303	0.2644	0.065*
C8	0.2357 (10)	0.4773 (4)	0.3601 (5)	0.042 (2)
H8	0.2440	0.5194	0.3790	0.050*
C9	0.0583 (11)	0.4540 (4)	0.3466 (5)	0.042 (2)
H9	0.0553	0.4132	0.3229	0.050*
C10	−0.0656 (11)	0.4897 (4)	0.2814 (5)	0.037 (2)
C11	0.0199 (12)	0.4480 (5)	0.4370 (5)	0.056 (3)
H11A	0.0089	0.4878	0.4594	0.067*
H11B	−0.0819	0.4275	0.4289	0.067*
C12	0.1489 (12)	0.4133 (4)	0.5046 (6)	0.057 (3)
H12A	0.1193	0.4127	0.5594	0.068*
H12B	0.1506	0.3721	0.4851	0.068*
C13	0.3157 (11)	0.4391 (4)	0.5209 (5)	0.041 (2)
C14	0.3449 (11)	0.4393 (5)	0.4269 (5)	0.047 (3)
H14	0.3326	0.3978	0.4054	0.056*
C15	0.5273 (12)	0.4556 (6)	0.4467 (5)	0.071 (3)
H15A	0.5447	0.4985	0.4549	0.085*
H15B	0.5729	0.4419	0.4004	0.085*
C16	0.5994 (12)	0.4197 (5)	0.5346 (6)	0.063 (3)
H16	0.6624	0.3854	0.5235	0.076*
C17	0.4585 (11)	0.3975 (4)	0.5674 (5)	0.049 (3)
H17	0.4323	0.3571	0.5434	0.059*
C18	0.3278 (12)	0.5029 (4)	0.5600 (5)	0.060 (3)
H18A	0.2615	0.5056	0.5997	0.090*
H18B	0.2926	0.5318	0.5140	0.090*
H18C	0.4370	0.5111	0.5908	0.090*
C19	−0.0940 (12)	0.5519 (5)	0.3155 (6)	0.067 (3)
H19A	−0.1539	0.5479	0.3582	0.101*
H19B	−0.1529	0.5763	0.2680	0.101*
H19C	0.0072	0.5706	0.3419	0.101*
C20	0.5091 (11)	0.3910 (4)	0.6663 (5)	0.046 (3)
C21	0.3696 (12)	0.3795 (5)	0.7090 (5)	0.064 (3)
H21A	0.4125	0.3670	0.7684	0.097*
H21B	0.3010	0.3486	0.6773	0.097*
H21C	0.3092	0.4159	0.7076	0.097*
C22	0.6418 (12)	0.3441 (4)	0.6935 (6)	0.056 (3)
H22	0.6460	0.3298	0.7524	0.068*
C23	0.7955 (12)	0.3809 (4)	0.6962 (6)	0.062 (3)
H23A	0.8727	0.3776	0.7527	0.074*
H23B	0.8449	0.3677	0.6513	0.074*
C24	0.7321 (12)	0.4448 (6)	0.6795 (6)	0.061 (3)
C25	0.8370 (12)	0.4942 (5)	0.7301 (5)	0.056 (3)
C26	1.0021 (12)	0.4945 (5)	0.7125 (6)	0.076 (3)
H26A	1.0697	0.5230	0.7504	0.114*
H26B	0.9916	0.5056	0.6528	0.114*
H26C	1.0486	0.4552	0.7231	0.114*
C27	0.7601 (14)	0.5553 (5)	0.7173 (7)	0.079 (4)
H27A	0.6515	0.5521	0.7208	0.118*
H27B	0.7614	0.5706	0.6610	0.118*
H27C	0.8183	0.5820	0.7618	0.118*
C28	−0.4053 (12)	0.4930 (5)	−0.0530 (7)	0.057 (3)
C29	−0.5343 (13)	0.5211 (6)	−0.1200 (5)	0.089 (4)
H29A	−0.5178	0.5137	−0.1765	0.113*
H29B	−0.5344	0.5636	−0.1099	0.113*
H29C	−0.6352	0.5044	−0.1176	0.113*
C30	−0.1479 (11)	0.2596 (4)	0.4140 (5)	0.050 (3)
H30A	−0.2411	0.2640	0.3647	0.060*
H30B	−0.1058	0.2996	0.4306	0.060*
C31	−0.2030 (10)	0.2316 (5)	0.4926 (5)	0.057 (3)
H31A	−0.2857	0.2561	0.5065	0.069*
H31B	−0.2442	0.1913	0.4786	0.069*
C32	−0.0500 (11)	0.2306 (5)	0.5702 (5)	0.052 (3)
H32	−0.0084	0.2712	0.5858	0.062*
C33	0.0751 (12)	0.1903 (5)	0.5471 (5)	0.056 (3)
H33A	0.1705	0.1890	0.5956	0.067*
H33B	0.0335	0.1497	0.5365	0.067*
C34	0.1180 (13)	0.2136 (5)	0.4664 (6)	0.065 (3)
C35	0.2708 (12)	0.2232 (6)	0.4694 (6)	0.073 (4)
H35	0.3462	0.2170	0.5224	0.087*
C36	0.3303 (11)	0.2431 (5)	0.3937 (5)	0.062 (3)
H36A	0.4226	0.2191	0.3915	0.074*
H36B	0.3645	0.2847	0.4022	0.074*
C37	0.2024 (11)	0.2373 (5)	0.3068 (5)	0.049 (3)
H37	0.1902	0.1955	0.2866	0.059*
C38	0.0422 (11)	0.2626 (4)	0.3204 (5)	0.044 (2)
H38	0.0649	0.3027	0.3464	0.053*
C39	−0.0217 (11)	0.2236 (4)	0.3847 (5)	0.040 (2)
C40	−0.0880 (11)	0.2702 (5)	0.2307 (5)	0.057 (3)
H40A	−0.1233	0.2308	0.2073	0.068*
H40B	−0.1799	0.2912	0.2405	0.068*
C41	−0.0238 (11)	0.3054 (4)	0.1634 (5)	0.051 (3)
H41A	−0.1062	0.3071	0.1086	0.061*
H41B	0.0000	0.3463	0.1839	0.061*
C42	0.1269 (11)	0.2771 (4)	0.1477 (5)	0.042 (2)
C43	0.2515 (10)	0.2778 (5)	0.2416 (5)	0.048 (3)
H43	0.2577	0.3190	0.2639	0.058*
C44	0.4132 (11)	0.2633 (5)	0.2200 (5)	0.060 (3)
H44A	0.5036	0.2774	0.2659	0.072*
H44B	0.4247	0.2204	0.2120	0.072*
C45	0.3995 (11)	0.2978 (4)	0.1344 (6)	0.052 (3)
H45	0.4735	0.3320	0.1453	0.063*
C46	0.2231 (9)	0.3210 (4)	0.1011 (5)	0.039 (2)
H46	0.2187	0.3614	0.1248	0.046*
C47	0.1024 (11)	0.2147 (4)	0.1089 (5)	0.050 (3)
H47A	0.0446	0.1907	0.1405	0.076*
H47B	0.2045	0.1965	0.1126	0.076*
H47C	0.0424	0.2172	0.0488	0.076*
C48	−0.0847 (13)	0.1635 (5)	0.3496 (6)	0.074 (3)
H48A	−0.0176	0.1471	0.3160	0.111*
H48B	−0.1918	0.1679	0.3132	0.111*
H48C	−0.0852	0.1370	0.3972	0.111*
C49	0.1748 (10)	0.3258 (4)	0.0014 (5)	0.039 (2)
C50	0.0006 (11)	0.3366 (5)	−0.0419 (5)	0.058 (3)
H50A	−0.0181	0.3331	−0.1040	0.087*
H50B	−0.0286	0.3761	−0.0275	0.087*
H50C	−0.0629	0.3073	−0.0217	0.087*
C51	0.2858 (13)	0.3733 (4)	−0.0286 (6)	0.052 (3)
H51	0.2345	0.3873	−0.0879	0.063*
C52	0.4308 (12)	0.3356 (4)	−0.0284 (6)	0.053 (3)
H52A	0.4560	0.3387	−0.0842	0.063*
H52B	0.5227	0.3493	0.0169	0.063*
C53	0.3917 (11)	0.2726 (5)	−0.0119 (6)	0.049 (3)
C54	0.4524 (11)	0.2230 (4)	−0.0628 (6)	0.048 (3)
C55	0.6336 (10)	0.2245 (5)	−0.0456 (6)	0.068 (3)
H55A	0.6660	0.1971	−0.0844	0.103*
H55B	0.6821	0.2129	0.0137	0.103*
H55C	0.6672	0.2645	−0.0552	0.103*
C56	0.3923 (13)	0.1628 (4)	−0.0470 (7)	0.075 (3)
H56A	0.2774	0.1632	−0.0626	0.113*
H56B	0.4321	0.1526	0.0135	0.113*
H56C	0.4286	0.1335	−0.0819	0.113*
C57	−0.0183 (14)	0.2215 (6)	0.7209 (7)	0.064 (3)
C58	−0.0760 (12)	0.1900 (6)	0.7928 (5)	0.081 (4)
H58A	−0.0585	0.1475	0.7903	0.112*
H58B	−0.1881	0.1976	0.7845	0.112*
H58C	−0.0175	0.2051	0.8487	0.112*
C59	0.5086 (16)	0.1378 (6)	0.6986 (9)	0.109 (5)
H59A	0.6156	0.1237	0.7238	0.113*
H59B	0.4769	0.1280	0.6376	0.113*
H59C	0.4369	0.1190	0.7274	0.113*
C60	0.1277 (17)	0.5753 (6)	0.9669 (8)	0.109 (5)
H60A	0.0398	0.5894	0.9879	0.114*
H60B	0.1243	0.5942	0.9122	0.114*
H60C	0.2268	0.5850	1.0086	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.050 (4)	0.082 (5)	0.034 (4)	0.002 (4)	0.011 (3)	−0.006 (4)
O2	0.065 (5)	0.115 (6)	0.038 (4)	0.004 (5)	0.001 (4)	−0.008 (4)
O3	0.042 (4)	0.085 (5)	0.031 (4)	0.008 (4)	0.012 (3)	0.005 (4)
O4	0.042 (4)	0.078 (5)	0.033 (3)	−0.005 (4)	0.016 (3)	−0.006 (3)
O5	0.108 (7)	0.079 (5)	0.068 (5)	0.008 (5)	0.048 (5)	0.000 (5)
O6	0.051 (5)	0.126 (7)	0.046 (4)	−0.027 (5)	0.002 (3)	0.015 (4)
O7	0.043 (4)	0.091 (5)	0.021 (3)	−0.004 (4)	0.011 (3)	0.002 (3)
O8	0.061 (6)	0.161 (9)	0.047 (4)	−0.030 (6)	0.011 (4)	0.000 (5)
O9	0.038 (4)	0.065 (5)	0.038 (4)	0.001 (3)	0.010 (3)	0.005 (3)
O10	0.037 (4)	0.057 (4)	0.034 (3)	−0.004 (3)	0.009 (3)	0.000 (3)
O11	0.075 (6)	0.061 (4)	0.058 (4)	−0.017 (4)	0.006 (4)	0.002 (4)
O12	0.061 (5)	0.114 (6)	0.030 (4)	0.016 (5)	0.011 (3)	−0.008 (4)
O13	0.099 (7)	0.098 (6)	0.084 (5)	−0.013 (6)	0.050 (6)	−0.008 (5)
O14	0.081 (6)	0.078 (6)	0.068 (5)	0.004 (5)	0.006 (5)	0.002 (4)
C1	0.045 (6)	0.073 (7)	0.041 (6)	−0.006 (6)	0.017 (5)	−0.009 (5)
C2	0.035 (6)	0.086 (8)	0.044 (6)	−0.025 (6)	0.017 (5)	−0.017 (6)
C3	0.049 (7)	0.058 (6)	0.036 (5)	0.010 (6)	0.009 (5)	−0.004 (5)
C4	0.049 (6)	0.061 (6)	0.024 (5)	−0.015 (6)	0.002 (4)	0.007 (5)
C5	0.056 (7)	0.046 (6)	0.046 (6)	0.001 (6)	0.017 (5)	−0.011 (5)
C6	0.053 (7)	0.074 (7)	0.028 (5)	0.006 (6)	0.016 (5)	0.003 (5)
C7	0.039 (6)	0.096 (8)	0.034 (5)	−0.018 (6)	0.023 (5)	0.006 (5)
C8	0.027 (5)	0.059 (6)	0.038 (5)	−0.005 (5)	0.008 (4)	−0.006 (5)
C9	0.053 (6)	0.041 (5)	0.036 (5)	−0.018 (5)	0.020 (5)	−0.016 (5)
C10	0.039 (6)	0.038 (5)	0.039 (5)	−0.009 (5)	0.018 (5)	−0.010 (5)
C11	0.051 (7)	0.086 (8)	0.037 (5)	−0.008 (6)	0.023 (5)	−0.001 (6)
C12	0.060 (7)	0.077 (7)	0.042 (6)	−0.013 (6)	0.028 (6)	−0.004 (5)
C13	0.035 (6)	0.053 (6)	0.043 (5)	−0.002 (5)	0.026 (4)	0.006 (5)
C14	0.040 (6)	0.074 (7)	0.035 (5)	0.002 (6)	0.024 (5)	−0.003 (5)
C15	0.067 (8)	0.124 (10)	0.018 (5)	0.002 (8)	0.005 (5)	0.001 (6)
C16	0.046 (7)	0.103 (9)	0.041 (6)	0.021 (7)	0.010 (5)	0.002 (6)
C17	0.057 (7)	0.059 (6)	0.040 (6)	0.003 (6)	0.029 (5)	0.004 (5)
C18	0.079 (8)	0.072 (7)	0.038 (5)	−0.001 (6)	0.031 (5)	0.002 (6)
C19	0.056 (7)	0.098 (9)	0.054 (6)	0.009 (7)	0.025 (6)	−0.002 (6)
C20	0.045 (6)	0.052 (6)	0.038 (6)	0.005 (6)	0.006 (5)	−0.003 (5)
C21	0.066 (8)	0.083 (8)	0.045 (6)	−0.008 (7)	0.017 (6)	0.016 (6)
C22	0.078 (9)	0.063 (7)	0.030 (5)	0.007 (7)	0.017 (5)	0.012 (5)
C23	0.056 (7)	0.067 (7)	0.065 (7)	0.034 (7)	0.020 (6)	0.027 (6)
C24	0.046 (7)	0.113 (9)	0.027 (6)	0.023 (7)	0.016 (5)	−0.006 (6)
C25	0.043 (6)	0.106 (9)	0.018 (5)	0.000 (7)	0.009 (5)	0.004 (6)
C26	0.060 (8)	0.107 (9)	0.069 (7)	−0.007 (7)	0.032 (6)	−0.008 (7)
C27	0.086 (10)	0.074 (8)	0.089 (8)	0.003 (8)	0.043 (7)	−0.014 (7)
C28	0.033 (6)	0.085 (8)	0.050 (7)	−0.004 (6)	0.007 (6)	0.014 (6)
C29	0.077 (9)	0.152 (12)	0.028 (6)	0.004 (9)	−0.002 (6)	0.016 (7)
C30	0.041 (6)	0.071 (7)	0.028 (5)	0.020 (6)	−0.005 (4)	0.009 (5)
C31	0.039 (6)	0.104 (9)	0.030 (5)	0.010 (6)	0.011 (5)	0.003 (6)
C32	0.056 (7)	0.073 (7)	0.029 (5)	0.006 (6)	0.015 (5)	0.005 (5)
C33	0.059 (7)	0.073 (7)	0.042 (6)	0.024 (6)	0.023 (5)	0.022 (5)
C34	0.067 (8)	0.093 (9)	0.038 (6)	0.014 (7)	0.016 (6)	0.023 (6)
C35	0.035 (7)	0.155 (12)	0.032 (5)	0.022 (7)	0.014 (5)	0.037 (7)
C36	0.031 (6)	0.118 (9)	0.033 (5)	0.010 (6)	0.003 (5)	0.021 (6)
C37	0.047 (6)	0.075 (7)	0.024 (5)	−0.007 (6)	0.010 (5)	0.006 (5)
C38	0.046 (6)	0.056 (6)	0.025 (5)	0.006 (5)	0.000 (4)	−0.001 (5)
C39	0.045 (6)	0.050 (6)	0.030 (5)	−0.007 (5)	0.019 (5)	−0.010 (5)
C40	0.038 (6)	0.083 (8)	0.046 (6)	0.007 (6)	0.003 (5)	0.013 (6)
C41	0.051 (7)	0.071 (7)	0.026 (5)	0.003 (6)	0.000 (5)	0.005 (5)
C42	0.040 (6)	0.057 (6)	0.019 (4)	0.006 (5)	−0.010 (4)	−0.003 (5)
C43	0.027 (6)	0.080 (7)	0.035 (5)	−0.005 (5)	0.004 (4)	−0.006 (5)
C44	0.048 (7)	0.111 (9)	0.013 (4)	−0.004 (7)	−0.003 (4)	0.020 (5)
C45	0.038 (6)	0.053 (6)	0.065 (7)	−0.008 (5)	0.012 (5)	−0.003 (6)
C46	0.018 (5)	0.065 (6)	0.029 (5)	0.007 (5)	−0.001 (4)	0.010 (5)
C47	0.050 (7)	0.044 (6)	0.053 (6)	0.001 (5)	0.006 (5)	−0.004 (5)
C48	0.079 (9)	0.102 (9)	0.050 (7)	−0.012 (8)	0.031 (6)	−0.013 (7)
C49	0.030 (6)	0.053 (6)	0.027 (5)	−0.001 (5)	−0.003 (4)	−0.006 (5)
C50	0.050 (7)	0.085 (7)	0.039 (5)	0.024 (6)	0.009 (5)	0.020 (6)
C51	0.074 (8)	0.050 (6)	0.032 (5)	−0.017 (6)	0.013 (5)	−0.008 (5)
C52	0.049 (7)	0.068 (7)	0.043 (6)	−0.017 (6)	0.015 (5)	0.006 (6)
C53	0.031 (6)	0.068 (7)	0.037 (6)	0.002 (6)	−0.011 (5)	−0.005 (5)
C54	0.035 (6)	0.063 (7)	0.044 (6)	−0.006 (6)	0.005 (5)	−0.001 (5)
C55	0.032 (6)	0.086 (8)	0.076 (7)	0.024 (6)	−0.006 (6)	−0.002 (7)
C56	0.069 (8)	0.067 (8)	0.101 (9)	−0.012 (7)	0.042 (7)	−0.015 (7)
C57	0.052 (8)	0.099 (9)	0.046 (7)	0.022 (7)	0.021 (6)	0.019 (7)
C58	0.048 (7)	0.162 (12)	0.037 (6)	0.007 (8)	0.017 (5)	0.023 (7)
C59	0.097 (11)	0.094 (10)	0.152 (13)	−0.019 (9)	0.061 (10)	0.004 (10)
C60	0.131 (13)	0.080 (10)	0.129 (12)	−0.003 (10)	0.055 (10)	−0.003 (9)

Geometric parameters (Å, º) top

O1—C28	1.314 (11)	C26—H26A	0.9600
O1—C3	1.453 (10)	C26—H26B	0.9600
O2—C28	1.246 (12)	C26—H26C	0.9600
O3—C24	1.418 (10)	C27—H27A	0.9600
O3—C16	1.428 (11)	C27—H27B	0.9600
O4—C24	1.407 (11)	C27—H27C	0.9600
O4—C20	1.424 (10)	C28—C29	1.464 (12)
O5—C22	1.416 (11)	C29—H29A	0.9600
O5—H5	0.8200	C29—H29B	0.9600
O6—C25	1.460 (9)	C29—H29C	0.9600
O6—H6	0.8200	C30—C39	1.524 (11)
O7—C57	1.344 (12)	C30—C31	1.579 (12)
O7—C32	1.481 (10)	C30—H30A	0.9700
O8—C57	1.183 (13)	C30—H30B	0.9700
O9—C53	1.408 (9)	C31—C32	1.553 (11)
O9—C45	1.445 (10)	C31—H31A	0.9700
O10—C53	1.411 (10)	C31—H31B	0.9700
O10—C49	1.475 (10)	C32—C33	1.525 (12)
O11—C51	1.409 (10)	C32—H32	0.9800
O11—H11	0.8200	C33—C34	1.517 (12)
O12—C54	1.461 (10)	C33—H33A	0.9700
O12—H12	0.8200	C33—H33B	0.9700
O13—C59	1.388 (14)	C34—C35	1.329 (13)
O13—H13	0.8200	C34—C39	1.539 (12)
O14—C60	1.383 (12)	C35—C36	1.495 (12)
O14—H14A	0.8200	C35—H35	0.9300
C1—C10	1.527 (12)	C36—C37	1.531 (10)
C1—C2	1.565 (11)	C36—H36A	0.9700
C1—H1A	0.9700	C36—H36B	0.9700
C1—H1B	0.9700	C37—C43	1.516 (12)
C2—C3	1.503 (11)	C37—C38	1.564 (12)
C2—H2A	0.9700	C37—H37	0.9800
C2—H2B	0.9700	C38—C39	1.551 (12)
C3—C4	1.500 (12)	C38—C40	1.575 (10)
C3—H3	0.9800	C38—H38	0.9800
C4—C5	1.507 (11)	C39—C48	1.494 (12)
C4—H4A	0.9700	C40—C41	1.543 (12)
C4—H4B	0.9700	C40—H40A	0.9700
C5—C6	1.317 (12)	C40—H40B	0.9700
C5—C10	1.566 (12)	C41—C42	1.528 (12)
C6—C7	1.449 (12)	C41—H41A	0.9700
C6—H6A	0.9300	C41—H41B	0.9700
C7—C8	1.526 (11)	C42—C47	1.511 (11)
C7—H7A	0.9700	C42—C46	1.589 (12)
C7—H7B	0.9700	C42—C43	1.594 (10)
C8—C14	1.486 (11)	C43—C44	1.561 (12)
C8—C9	1.582 (12)	C43—H43	0.9800
C8—H8	0.9800	C44—C45	1.539 (11)
C9—C10	1.507 (11)	C44—H44A	0.9700
C9—C11	1.564 (11)	C44—H44B	0.9700
C9—H9	0.9800	C45—C46	1.566 (11)
C10—C19	1.530 (12)	C45—H45	0.9800
C11—C12	1.537 (12)	C46—C49	1.532 (10)
C11—H11A	0.9700	C46—H46	0.9800
C11—H11B	0.9700	C47—H47A	0.9600
C12—C13	1.512 (12)	C47—H47B	0.9600
C12—H12A	0.9700	C47—H47C	0.9600
C12—H12B	0.9700	C48—H48A	0.9600
C13—C18	1.542 (12)	C48—H48B	0.9600
C13—C17	1.565 (12)	C48—H48C	0.9600
C13—C14	1.579 (11)	C49—C50	1.503 (11)
C14—C15	1.569 (13)	C49—C51	1.585 (12)
C14—H14	0.9800	C50—H50A	0.9600
C15—C16	1.586 (12)	C50—H50B	0.9600
C15—H15A	0.9700	C50—H50C	0.9600
C15—H15B	0.9700	C51—C52	1.510 (13)
C16—C17	1.530 (13)	C51—H51	0.9800
C16—H16	0.9800	C52—C53	1.481 (13)
C17—C20	1.523 (11)	C52—H52A	0.9700
C17—H17	0.9800	C52—H52B	0.9700
C18—H18A	0.9600	C53—C54	1.540 (13)
C18—H18B	0.9600	C54—C56	1.483 (12)
C18—H18C	0.9600	C54—C55	1.520 (12)
C19—H19A	0.9600	C55—H55A	0.9600
C19—H19B	0.9600	C55—H55B	0.9600
C19—H19C	0.9600	C55—H55C	0.9600
C20—C22	1.527 (13)	C56—H56A	0.9600
C20—C21	1.555 (13)	C56—H56B	0.9600
C21—H21A	0.9600	C56—H56C	0.9600
C21—H21B	0.9600	C57—C58	1.533 (14)
C21—H21C	0.9600	C58—H58A	0.9600
C22—C23	1.553 (13)	C58—H58B	0.9600
C22—H22	0.9800	C58—H58C	0.9600
C23—C24	1.523 (14)	C59—H59A	0.9600
C23—H23A	0.9700	C59—H59B	0.9600
C23—H23B	0.9700	C59—H59C	0.9600
C24—C25	1.514 (14)	C60—H60A	0.9600
C25—C27	1.502 (13)	C60—H60B	0.9600
C25—C26	1.527 (13)	C60—H60C	0.9600

C28—O1—C3	119.0 (8)	C39—C30—C31	115.1 (7)
C24—O3—C16	111.5 (8)	C39—C30—H30A	108.5
C24—O4—C20	104.2 (7)	C31—C30—H30A	108.5
C22—O5—H5	109.5	C39—C30—H30B	108.5
C25—O6—H6	109.5	C31—C30—H30B	108.5
C57—O7—C32	112.3 (7)	H30A—C30—H30B	107.5
C53—O9—C45	112.7 (7)	C32—C31—C30	105.1 (7)
C53—O10—C49	104.1 (6)	C32—C31—H31A	110.7
C51—O11—H11	109.5	C30—C31—H31A	110.7
C54—O12—H12	109.5	C32—C31—H31B	110.7
C59—O13—H13	109.5	C30—C31—H31B	110.7
C60—O14—H14A	109.5	H31A—C31—H31B	108.8
C10—C1—C2	114.4 (8)	O7—C32—C33	108.6 (7)
C10—C1—H1A	108.7	O7—C32—C31	104.2 (7)
C2—C1—H1A	108.7	C33—C32—C31	109.2 (7)
C10—C1—H1B	108.7	O7—C32—H32	111.5
C2—C1—H1B	108.7	C33—C32—H32	111.5
H1A—C1—H1B	107.6	C31—C32—H32	111.5
C3—C2—C1	107.2 (8)	C34—C33—C32	110.5 (8)
C3—C2—H2A	110.3	C34—C33—H33A	109.6
C1—C2—H2A	110.3	C32—C33—H33A	109.6
C3—C2—H2B	110.3	C34—C33—H33B	109.6
C1—C2—H2B	110.3	C32—C33—H33B	109.6
H2A—C2—H2B	108.5	H33A—C33—H33B	108.1
O1—C3—C4	108.4 (7)	C35—C34—C33	119.3 (9)
O1—C3—C2	106.3 (8)	C35—C34—C39	124.1 (8)
C4—C3—C2	111.3 (7)	C33—C34—C39	116.7 (9)
O1—C3—H3	110.3	C34—C35—C36	124.8 (9)
C4—C3—H3	110.3	C34—C35—H35	117.6
C2—C3—H3	110.3	C36—C35—H35	117.6
C3—C4—C5	113.3 (7)	C35—C36—C37	112.3 (8)
C3—C4—H4A	108.9	C35—C36—H36A	109.1
C5—C4—H4A	108.9	C37—C36—H36A	109.1
C3—C4—H4B	108.9	C35—C36—H36B	109.1
C5—C4—H4B	108.9	C37—C36—H36B	109.2
H4A—C4—H4B	107.7	H36A—C36—H36B	107.9
C6—C5—C4	122.1 (8)	C43—C37—C36	107.4 (7)
C6—C5—C10	121.2 (9)	C43—C37—C38	107.5 (8)
C4—C5—C10	116.5 (8)	C36—C37—C38	107.6 (7)
C5—C6—C7	126.5 (8)	C43—C37—H37	111.4
C5—C6—H6A	116.7	C36—C37—H37	111.4
C7—C6—H6A	116.7	C38—C37—H37	111.4
C6—C7—C8	115.2 (8)	C39—C38—C37	111.9 (7)
C6—C7—H7A	108.5	C39—C38—C40	111.2 (8)
C8—C7—H7A	108.5	C37—C38—C40	111.2 (7)
C6—C7—H7B	108.5	C39—C38—H38	107.4
C8—C7—H7B	108.5	C37—C38—H38	107.4
H7A—C7—H7B	107.5	C40—C38—H38	107.4
C14—C8—C7	111.2 (8)	C48—C39—C30	111.4 (8)
C14—C8—C9	108.8 (7)	C48—C39—C34	108.3 (8)
C7—C8—C9	106.2 (7)	C30—C39—C34	106.6 (7)
C14—C8—H8	110.2	C48—C39—C38	114.5 (7)
C7—C8—H8	110.2	C30—C39—C38	108.4 (7)
C9—C8—H8	110.2	C34—C39—C38	107.4 (7)
C10—C9—C11	113.0 (8)	C41—C40—C38	112.3 (8)
C10—C9—C8	114.2 (7)	C41—C40—H40A	109.2
C11—C9—C8	109.8 (7)	C38—C40—H40A	109.2
C10—C9—H9	106.4	C41—C40—H40B	109.2
C11—C9—H9	106.4	C38—C40—H40B	109.2
C8—C9—H9	106.4	H40A—C40—H40B	107.9
C9—C10—C1	109.8 (7)	C42—C41—C40	112.5 (8)
C9—C10—C19	112.6 (7)	C42—C41—H41A	109.1
C1—C10—C19	110.3 (8)	C40—C41—H41A	109.1
C9—C10—C5	109.0 (7)	C42—C41—H41B	109.1
C1—C10—C5	107.9 (7)	C40—C41—H41B	109.1
C19—C10—C5	107.0 (7)	H41A—C41—H41B	107.8
C12—C11—C9	113.2 (8)	C47—C42—C41	114.3 (8)
C12—C11—H11A	108.9	C47—C42—C46	114.1 (7)
C9—C11—H11A	108.9	C41—C42—C46	113.4 (7)
C12—C11—H11B	108.9	C47—C42—C43	112.2 (7)
C9—C11—H11B	108.9	C41—C42—C43	103.9 (7)
H11A—C11—H11B	107.8	C46—C42—C43	97.0 (7)
C13—C12—C11	114.5 (8)	C37—C43—C44	117.2 (8)
C13—C12—H12A	108.6	C37—C43—C42	113.0 (7)
C11—C12—H12A	108.6	C44—C43—C42	102.6 (6)
C13—C12—H12B	108.6	C37—C43—H43	107.9
C11—C12—H12B	108.6	C44—C43—H43	107.8
H12A—C12—H12B	107.6	C42—C43—H43	107.8
C12—C13—C18	112.2 (8)	C45—C44—C43	103.1 (7)
C12—C13—C17	117.1 (7)	C45—C44—H44A	111.1
C18—C13—C17	113.2 (8)	C43—C44—H44A	111.1
C12—C13—C14	102.9 (7)	C45—C44—H44B	111.1
C18—C13—C14	111.6 (7)	C43—C44—H44B	111.1
C17—C13—C14	98.3 (7)	H44A—C44—H44B	109.1
C8—C14—C15	115.4 (8)	O9—C45—C44	105.8 (7)
C8—C14—C13	116.5 (7)	O9—C45—C46	114.1 (7)
C15—C14—C13	102.4 (7)	C44—C45—C46	107.7 (7)
C8—C14—H14	107.3	O9—C45—H45	109.7
C15—C14—H14	107.3	C44—C45—H45	109.7
C13—C14—H14	107.3	C46—C45—H45	109.7
C14—C15—C16	101.6 (8)	C49—C46—C45	110.4 (7)
C14—C15—H15A	111.5	C49—C46—C42	119.4 (7)
C16—C15—H15A	111.4	C45—C46—C42	102.9 (6)
C14—C15—H15B	111.4	C49—C46—H46	107.9
C16—C15—H15B	111.5	C45—C46—H46	107.9
H15A—C15—H15B	109.3	C42—C46—H46	107.9
O3—C16—C17	114.7 (7)	C42—C47—H47A	109.5
O3—C16—C15	104.7 (8)	C42—C47—H47B	109.5
C17—C16—C15	107.4 (8)	H47A—C47—H47B	109.5
O3—C16—H16	110.0	C42—C47—H47C	109.5
C17—C16—H16	110.0	H47A—C47—H47C	109.5
C15—C16—H16	110.0	H47B—C47—H47C	109.5
C20—C17—C16	110.1 (8)	C39—C48—H48A	109.5
C20—C17—C13	121.3 (8)	C39—C48—H48B	109.5
C16—C17—C13	104.5 (7)	H48A—C48—H48B	109.5
C20—C17—H17	106.7	C39—C48—H48C	109.5
C16—C17—H17	106.7	H48A—C48—H48C	109.5
C13—C17—H17	106.7	H48B—C48—H48C	109.5
C13—C18—H18A	109.5	O10—C49—C50	107.3 (7)
C13—C18—H18B	109.5	O10—C49—C46	110.7 (7)
H18A—C18—H18B	109.5	C50—C49—C46	116.8 (7)
C13—C18—H18C	109.5	O10—C49—C51	99.1 (7)
H18A—C18—H18C	109.5	C50—C49—C51	111.8 (8)
H18B—C18—H18C	109.5	C46—C49—C51	109.6 (7)
C10—C19—H19A	109.5	C49—C50—H50A	109.5
C10—C19—H19B	109.5	C49—C50—H50B	109.5
H19A—C19—H19B	109.5	H50A—C50—H50B	109.5
C10—C19—H19C	109.5	C49—C50—H50C	109.5
H19A—C19—H19C	109.5	H50A—C50—H50C	109.5
H19B—C19—H19C	109.5	H50B—C50—H50C	109.5
O4—C20—C17	109.9 (8)	O11—C51—C52	112.1 (8)
O4—C20—C22	101.9 (7)	O11—C51—C49	112.6 (7)
C17—C20—C22	110.3 (8)	C52—C51—C49	101.4 (7)
O4—C20—C21	106.8 (7)	O11—C51—H51	110.2
C17—C20—C21	114.9 (8)	C52—C51—H51	110.2
C22—C20—C21	112.2 (8)	C49—C51—H51	110.2
C20—C21—H21A	109.5	C53—C52—C51	107.3 (8)
C20—C21—H21B	109.5	C53—C52—H52A	110.3
H21A—C21—H21B	109.5	C51—C52—H52A	110.3
C20—C21—H21C	109.5	C53—C52—H52B	110.3
H21A—C21—H21C	109.5	C51—C52—H52B	110.3
H21B—C21—H21C	109.5	H52A—C52—H52B	108.5
O5—C22—C20	114.9 (8)	O9—C53—O10	109.6 (7)
O5—C22—C23	111.3 (9)	O9—C53—C52	113.5 (7)
C20—C22—C23	102.9 (8)	O10—C53—C52	103.6 (8)
O5—C22—H22	109.2	O9—C53—C54	105.1 (7)
C20—C22—H22	109.2	O10—C53—C54	107.5 (7)
C23—C22—H22	109.2	C52—C53—C54	117.3 (8)
C24—C23—C22	102.7 (8)	O12—C54—C56	108.8 (8)
C24—C23—H23A	111.2	O12—C54—C55	104.0 (7)
C22—C23—H23A	111.2	C56—C54—C55	112.4 (9)
C24—C23—H23B	111.2	O12—C54—C53	107.4 (7)
C22—C23—H23B	111.2	C56—C54—C53	112.1 (8)
H23A—C23—H23B	109.1	C55—C54—C53	111.7 (8)
O4—C24—O3	109.9 (7)	C54—C55—H55A	109.5
O4—C24—C25	107.9 (7)	C54—C55—H55B	109.5
O3—C24—C25	105.2 (9)	H55A—C55—H55B	109.5
O4—C24—C23	104.3 (9)	C54—C55—H55C	109.5
O3—C24—C23	112.9 (8)	H55A—C55—H55C	109.5
C25—C24—C23	116.5 (8)	H55B—C55—H55C	109.5
O6—C25—C27	107.3 (9)	C54—C56—H56A	109.5
O6—C25—C24	108.2 (8)	C54—C56—H56B	109.5
C27—C25—C24	113.7 (9)	H56A—C56—H56B	109.5
O6—C25—C26	103.6 (7)	C54—C56—H56C	109.5
C27—C25—C26	112.0 (9)	H56A—C56—H56C	109.5
C24—C25—C26	111.5 (9)	H56B—C56—H56C	109.5
C25—C26—H26A	109.5	O8—C57—O7	125.2 (10)
C25—C26—H26B	109.5	O8—C57—C58	124.6 (10)
H26A—C26—H26B	109.5	O7—C57—C58	110.1 (10)
C25—C26—H26C	109.5	C57—C58—H58A	109.5
H26A—C26—H26C	109.5	C57—C58—H58B	109.5
H26B—C26—H26C	109.5	H58A—C58—H58B	109.5
C25—C27—H27A	109.5	C57—C58—H58C	109.5
C25—C27—H27B	109.5	H58A—C58—H58C	109.5
H27A—C27—H27B	109.5	H58B—C58—H58C	109.5
C25—C27—H27C	109.5	O13—C59—H59A	109.5
H27A—C27—H27C	109.5	O13—C59—H59B	109.5
H27B—C27—H27C	109.5	H59A—C59—H59B	109.5
O2—C28—O1	120.9 (9)	O13—C59—H59C	109.5
O2—C28—C29	124.1 (10)	H59A—C59—H59C	109.5
O1—C28—C29	114.5 (10)	H59B—C59—H59C	109.5
C28—C29—H29A	109.5	O14—C60—H60A	109.5
C28—C29—H29B	109.5	O14—C60—H60B	109.5
H29A—C29—H29B	109.5	H60A—C60—H60B	109.5
C28—C29—H29C	109.5	O14—C60—H60C	109.5
H29A—C29—H29C	109.5	H60A—C60—H60C	109.5
H29B—C29—H29C	109.5	H60B—C60—H60C	109.5

C10—C1—C2—C3	61.6 (10)	C39—C30—C31—C32	62.4 (10)
C28—O1—C3—C4	88.5 (10)	C57—O7—C32—C33	92.9 (9)
C28—O1—C3—C2	−151.8 (8)	C57—O7—C32—C31	−150.8 (8)
C1—C2—C3—O1	−178.3 (7)	C30—C31—C32—O7	−178.0 (7)
C1—C2—C3—C4	−60.5 (10)	C30—C31—C32—C33	−62.2 (10)
O1—C3—C4—C5	171.8 (7)	O7—C32—C33—C34	173.0 (8)
C2—C3—C4—C5	55.2 (11)	C31—C32—C33—C34	60.0 (11)
C3—C4—C5—C6	128.5 (10)	C32—C33—C34—C35	126.8 (12)
C3—C4—C5—C10	−46.8 (11)	C32—C33—C34—C39	−54.2 (12)
C4—C5—C6—C7	178.2 (9)	C33—C34—C35—C36	176.8 (10)
C10—C5—C6—C7	−6.7 (16)	C39—C34—C35—C36	−2 (2)
C5—C6—C7—C8	−9.6 (16)	C34—C35—C36—C37	−13.5 (18)
C6—C7—C8—C14	158.6 (8)	C35—C36—C37—C43	160.3 (9)
C6—C7—C8—C9	40.4 (12)	C35—C36—C37—C38	44.8 (12)
C14—C8—C9—C10	178.8 (7)	C43—C37—C38—C39	178.6 (7)
C7—C8—C9—C10	−61.4 (10)	C36—C37—C38—C39	−65.9 (10)
C14—C8—C9—C11	50.7 (10)	C43—C37—C38—C40	53.6 (10)
C7—C8—C9—C11	170.5 (8)	C36—C37—C38—C40	169.0 (8)
C11—C9—C10—C1	−68.8 (9)	C31—C30—C39—C48	64.0 (9)
C8—C9—C10—C1	164.8 (7)	C31—C30—C39—C34	−53.9 (10)
C11—C9—C10—C19	54.6 (10)	C31—C30—C39—C38	−169.2 (7)
C8—C9—C10—C19	−71.8 (9)	C35—C34—C39—C48	108.0 (13)
C11—C9—C10—C5	173.2 (7)	C33—C34—C39—C48	−70.9 (11)
C8—C9—C10—C5	46.7 (9)	C35—C34—C39—C30	−132.1 (12)
C2—C1—C10—C9	−170.2 (7)	C33—C34—C39—C30	49.1 (12)
C2—C1—C10—C19	65.1 (9)	C35—C34—C39—C38	−16.1 (15)
C2—C1—C10—C5	−51.5 (10)	C33—C34—C39—C38	165.0 (8)
C6—C5—C10—C9	−12.4 (12)	C37—C38—C39—C48	−70.8 (10)
C4—C5—C10—C9	162.9 (7)	C40—C38—C39—C48	54.3 (11)
C6—C5—C10—C1	−131.6 (9)	C37—C38—C39—C30	164.3 (7)
C4—C5—C10—C1	43.7 (11)	C40—C38—C39—C30	−70.6 (9)
C6—C5—C10—C19	109.7 (10)	C37—C38—C39—C34	49.5 (10)
C4—C5—C10—C19	−75.0 (10)	C40—C38—C39—C34	174.6 (8)
C10—C9—C11—C12	−178.1 (7)	C39—C38—C40—C41	−176.3 (7)
C8—C9—C11—C12	−49.3 (10)	C37—C38—C40—C41	−50.8 (11)
C9—C11—C12—C13	56.3 (11)	C38—C40—C41—C42	55.9 (11)
C11—C12—C13—C18	63.4 (10)	C40—C41—C42—C47	63.3 (9)
C11—C12—C13—C17	−163.2 (7)	C40—C41—C42—C46	−163.5 (7)
C11—C12—C13—C14	−56.7 (10)	C40—C41—C42—C43	−59.4 (10)
C7—C8—C14—C15	62.0 (11)	C36—C37—C43—C44	61.9 (10)
C9—C8—C14—C15	178.6 (8)	C38—C37—C43—C44	177.4 (7)
C7—C8—C14—C13	−177.8 (8)	C36—C37—C43—C42	−179.1 (8)
C9—C8—C14—C13	−61.2 (10)	C38—C37—C43—C42	−63.6 (10)
C12—C13—C14—C8	62.4 (10)	C47—C42—C43—C37	−58.2 (11)
C18—C13—C14—C8	−58.2 (11)	C41—C42—C43—C37	65.8 (10)
C17—C13—C14—C8	−177.3 (8)	C46—C42—C43—C37	−177.9 (8)
C12—C13—C14—C15	−170.7 (8)	C47—C42—C43—C44	68.9 (10)
C18—C13—C14—C15	68.7 (10)	C41—C42—C43—C44	−167.0 (8)
C17—C13—C14—C15	−50.4 (9)	C46—C42—C43—C44	−50.7 (9)
C8—C14—C15—C16	165.7 (7)	C37—C43—C44—C45	162.7 (7)
C13—C14—C15—C16	38.1 (10)	C42—C43—C44—C45	38.2 (10)
C24—O3—C16—C17	42.6 (10)	C53—O9—C45—C44	160.6 (7)
C24—O3—C16—C15	159.9 (7)	C53—O9—C45—C46	42.4 (10)
C14—C15—C16—O3	−133.3 (8)	C43—C44—C45—O9	−132.2 (8)
C14—C15—C16—C17	−11.0 (10)	C43—C44—C45—C46	−9.8 (10)
O3—C16—C17—C20	−36.4 (11)	O9—C45—C46—C49	−33.7 (10)
C15—C16—C17—C20	−152.2 (8)	C44—C45—C46—C49	−150.7 (8)
O3—C16—C17—C13	95.4 (8)	O9—C45—C46—C42	94.9 (8)
C15—C16—C17—C13	−20.5 (10)	C44—C45—C46—C42	−22.2 (9)
C12—C13—C17—C20	−82.9 (11)	C47—C42—C46—C49	48.1 (10)
C18—C13—C17—C20	50.1 (11)	C41—C42—C46—C49	−85.2 (10)
C14—C13—C17—C20	168.0 (8)	C43—C42—C46—C49	166.3 (8)
C12—C13—C17—C16	152.2 (8)	C47—C42—C46—C45	−74.5 (8)
C18—C13—C17—C16	−74.8 (9)	C41—C42—C46—C45	152.1 (7)
C14—C13—C17—C16	43.1 (9)	C43—C42—C46—C45	43.7 (8)
C24—O4—C20—C17	−67.8 (9)	C53—O10—C49—C50	165.5 (7)
C24—O4—C20—C22	49.2 (8)	C53—O10—C49—C46	−66.0 (8)
C24—O4—C20—C21	167.0 (7)	C53—O10—C49—C51	49.2 (7)
C16—C17—C20—O4	49.4 (10)	C45—C46—C49—O10	46.0 (9)
C13—C17—C20—O4	−72.9 (10)	C42—C46—C49—O10	−73.0 (9)
C16—C17—C20—C22	−62.2 (11)	C45—C46—C49—C50	169.2 (8)
C13—C17—C20—C22	175.5 (8)	C42—C46—C49—C50	50.3 (12)
C16—C17—C20—C21	169.8 (9)	C45—C46—C49—C51	−62.4 (10)
C13—C17—C20—C21	47.6 (12)	C42—C46—C49—C51	178.7 (7)
O4—C20—C22—O5	−153.3 (7)	O10—C49—C51—O11	−152.6 (7)
C17—C20—C22—O5	−36.6 (11)	C50—C49—C51—O11	94.5 (9)
C21—C20—C22—O5	92.8 (10)	C46—C49—C51—O11	−36.6 (10)
O4—C20—C22—C23	−32.1 (8)	O10—C49—C51—C52	−32.6 (7)
C17—C20—C22—C23	84.5 (9)	C50—C49—C51—C52	−145.5 (7)
C21—C20—C22—C23	−146.0 (8)	C46—C49—C51—C52	83.3 (9)
O5—C22—C23—C24	129.2 (8)	O11—C51—C52—C53	127.3 (8)
C20—C22—C23—C24	5.6 (9)	C49—C51—C52—C53	7.0 (9)
C20—O4—C24—O3	75.3 (9)	C45—O9—C53—O10	−65.0 (9)
C20—O4—C24—C25	−170.5 (7)	C45—O9—C53—C52	50.3 (10)
C20—O4—C24—C23	−46.0 (8)	C45—O9—C53—C54	179.8 (7)
C16—O3—C24—O4	−62.7 (10)	C49—O10—C53—O9	75.5 (8)
C16—O3—C24—C25	−178.6 (7)	C49—O10—C53—C52	−46.0 (8)
C16—O3—C24—C23	53.3 (10)	C49—O10—C53—C54	−170.8 (7)
C22—C23—C24—O4	23.3 (9)	C51—C52—C53—O9	−96.0 (9)
C22—C23—C24—O3	−96.0 (9)	C51—C52—C53—O10	22.8 (9)
C22—C23—C24—C25	142.1 (8)	C51—C52—C53—C54	141.1 (8)
O4—C24—C25—O6	61.8 (10)	O9—C53—C54—O12	177.8 (7)
O3—C24—C25—O6	179.1 (7)	O10—C53—C54—O12	61.1 (9)
C23—C24—C25—O6	−55.1 (11)	C52—C53—C54—O12	−55.0 (10)
O4—C24—C25—C27	−57.3 (10)	O9—C53—C54—C56	58.4 (10)
O3—C24—C25—C27	60.0 (10)	O10—C53—C54—C56	−58.3 (10)
C23—C24—C25—C27	−174.1 (8)	C52—C53—C54—C56	−174.4 (9)
O4—C24—C25—C26	175.1 (8)	O9—C53—C54—C55	−68.7 (10)
O3—C24—C25—C26	−67.7 (10)	O10—C53—C54—C55	174.6 (8)
C23—C24—C25—C26	58.2 (11)	C52—C53—C54—C55	58.4 (11)
C3—O1—C28—O2	5.0 (14)	C32—O7—C57—O8	−2.9 (15)
C3—O1—C28—C29	177.3 (9)	C32—O7—C57—C58	−179.0 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O13	0.82	1.92	2.742 (11)	178
O6—H6···O2ⁱ	0.82	2.25	2.752 (10)	120
O12—H12···O8ⁱⁱ	0.82	2.42	2.780 (10)	108
O11—H11···O14ⁱⁱ	0.82	2.00	2.755 (10)	153
O12—H12···O10	0.82	2.47	2.776 (8)	104
O13—H13···O12ⁱⁱⁱ	0.82	2.19	2.708 (9)	121
O14—H14A···O6^iv	0.82	2.03	2.673 (9)	135

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

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