Disordered 2,2′,3,3′,4,6,6′-hepta-O-pivaloyl-α,α′-trehalose

Baddeley, T.C.; Clow, S.M.; Cox, P.J.; Davidson, I.G.; Murdoch, A.M.; Wardell, J.L.

doi:10.1107/S1600536803009474

Disordered 2,2′,3,3′,4,6,6′-hepta-O-pivaloyl-α,α′-trehalose

T. C. Baddeley, S. M. Clow, P. J. Cox, I. G. Davidson, A. M. Murdoch and J. L. Wardell

The structure of the title compound, C₄₇H₇₈O₁₈, is characterized by intermolecular hydrogen bonding and a disordered pivaloyl group.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009474/cm6040sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009474/cm6040Isup2.hkl Contains datablock I

CCDC reference: 214808

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.009 Å
R factor = 0.078
wR factor = 0.234
Data-to-parameter ratio = 9.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



DIFMX_01  Alert C The maximum difference density is > 0.1*ZMAX*0.75
          _refine_diff_density_max given =      0.689
          Test value =      0.600

DIFMX_02  Alert C The minimum difference density is > 0.1*ZMAX*0.75
          The relevant atom site should be identified.

PLAT_213  Alert C Atom C13'    has ADP max/min Ratio ...........       3.20 prolate

PLAT_601  Alert C Structure Contains Solvent Accessible VOIDS of      37.00 A   3

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.38
         From the CIF: _reflns_number_total               5812
         Count of symmetry unique reflns         5828
         Completeness (_total/calc)             99.73%
         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
          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.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 4 Alert Level C = Please check

Comment top

In continuation of our recent investigations of the structures and derivatives of the symmetric and non-reducing disaccharide, α,α'-trehalose (Clow et al., 2001; Baddeley et al., 2001, 2002), we have determined the structure of 2,2',3,3',4,6,6'-hepta-O-pivaloyl-α,α'-trehalose, (I). As in the symmetric substituted derivatives, e.g. 2,2',3,3',4,4',6,6'-hexa-O-acetato-α,α'-trehalose EtOAc solvate (Baddeley et al., 2001), 2,2',3,3',4,4'-hexa-O-acetato-6,6'-bis-O-isobutanoyl-α,α'-trehalose 0.7-hydrate (Clow et al., 2001), and 2,2',3,3',4,4'-hexa-O-acetato-6,6'-bis-O-trityl-α,α'-trehalose (Baddeley et al., 2002), both pyranose rings in (I) have near ideal ⁴C₁ conformations. The corresponding puckering parameters (Cremer & Pople, 1975) calculated with PLATON (Spek, 2001) are Q = 0.571 (5) Å, θ = 4.5 (5)° and ø = 319 (5)° (unprimed atoms), and Q = 0.568 (5) Å, θ = 5.5 (5)°, ø = 317 (5)° (primed atoms). The arrangement and packing of the bulky pivaloyl groups thus do not lead to any significant changes in the pyranose conformations.

The pseudo-torsion angle H1—C1···C1'—H1' of the glycosidic linkage is −85.3°. In the ditrityl hexaacetate derivative of α,α'-trehalose, the bridging O atom lies on a twofold axis and the pseudo-torsion angle is −104.7° (Baddeley et al., 2002).

The substitution at C1,C1' is α,α', with C1—O1 = 1.423 (5) Å and C1'-O1 = 1.424 (5) Å. The angle subtended at O1 is 111.1 (3)°. The absolute configuration adopted, see below, is R at C1, C1', C2, C2', C4, C4', C5 and C5', and S at C3 and C3'. Intermolecular hydrogen bonding links the OH group at C4' with a carbonyl oxygen in the –OCOC(CH₃)₃ group at the C2 position. This results in a hydrogen-bonding motif consisting of chains of molecules along the twofold b axis. Additional intermolecular C—H···O hydrogen bonding is also present (Table 2). A small peak (0.689 e Å⁻³) on the final difference map may possibly be a disordered oxygen of a water molecule with a very low occupation factor but its proximity to C25 (about 2.4 Å) requires disorder at this carbon. Disorder is present in the pivaloyl group with atoms C18, C19 and C20 each spread over two sites with occupancies of 0.49 (2) and 0.51 (2).

Experimental top

The title compound was prepared by an esterification method involving suspension of α,α'-trehalose in pyridine, cooling to 253 K, slow addition of pivaloyl chloride and stirring at room temp for 3 d. The reaction mixture was poured into ice water and extracted into chloroform. Following chromatography using 7:2 light petroleum:diethyl ether, suitable crystals of the isolated product were grown by slow evaporation of a 95% ethanol solution (m.p. 453–455 K).

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al.,1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).

Figures top

Fig. 1. The atomic arrangement in the molecule (disorder excluded). Displacement ellipsoids are shown at the 50% probability level.

2,2',3,3',4,6,6'-hepta-O-pivalato-α,α'-trehalose top

Crystal data top

C₄₇H₇₈O₁₈	F(000) = 1008
M_r = 931.09	D_x = 1.145 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 14.1855 (3) Å	Cell parameters from 5000 reflections
b = 10.6390 (2) Å	θ = 1.5–26.0°
c = 18.3343 (4) Å	µ = 0.09 mm⁻¹
β = 102.5721 (9)°	T = 150 K
V = 2700.66 (10) Å³	Lozenge, colourless
Z = 2	0.55 × 0.20 × 0.20 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	5812 independent reflections
Radiation source: Enraf-Nonius FR591 rotating anode	4797 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
Detector resolution: 9.091 pixels mm^-1	θ_max = 26.4°, θ_min = 1.5°
ϕ and ω scans to fill Ewald sphere	h = −17→17
Absorption correction: multi-scan multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995, 1997)	k = −13→13
T_min = 0.954, T_max = 0.983	l = −22→22
45444 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.078	H-atom parameters constrained
wR(F²) = 0.234	w = 1/[σ²(F_o²) + (0.1602P)² + 1.3102P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.013
5812 reflections	Δρ_max = 0.69 e Å⁻³
586 parameters	Δρ_min = −0.31 e Å⁻³
199 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (3)

Crystal data top

C₄₇H₇₈O₁₈	V = 2700.66 (10) Å³
M_r = 931.09	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 14.1855 (3) Å	µ = 0.09 mm⁻¹
b = 10.6390 (2) Å	T = 150 K
c = 18.3343 (4) Å	0.55 × 0.20 × 0.20 mm
β = 102.5721 (9)°

Data collection top

Nonius KappaCCD area-detector diffractometer	5812 independent reflections
Absorption correction: multi-scan multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995, 1997)	4797 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.983	R_int = 0.072
45444 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	199 restraints
wR(F²) = 0.234	H-atom parameters constrained
S = 1.03	Δρ_max = 0.69 e Å⁻³
5812 reflections	Δρ_min = −0.31 e Å⁻³
586 parameters

Special details top

Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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	Occ. (<1)
O1	0.7142 (2)	0.7414 (3)	0.14034 (16)	0.0323 (7)
O2	0.5326 (2)	0.7820 (3)	0.16472 (18)	0.0338 (7)
O3	0.3935 (3)	0.6784 (5)	0.1442 (4)	0.0859 (18)
O4	0.5614 (2)	0.7130 (3)	0.31776 (17)	0.0325 (7)
O5	0.7140 (2)	0.5342 (3)	0.18155 (19)	0.0388 (7)
O6	0.6377 (4)	0.8739 (6)	0.3812 (3)	0.095 (2)
O7	0.7669 (2)	0.6335 (4)	0.37633 (18)	0.0407 (8)
O8	0.6878 (4)	0.5175 (7)	0.4445 (3)	0.0897 (18)
O9	0.7859 (2)	0.3501 (3)	0.2919 (2)	0.0485 (9)
O10	0.9239 (3)	0.2564 (5)	0.3388 (3)	0.0692 (13)
O2'	0.9069 (2)	0.8168 (3)	0.16592 (17)	0.0368 (7)
O3'	0.9823 (4)	0.6473 (5)	0.1352 (2)	0.0791 (16)
O4'	0.8905 (2)	1.0310 (4)	0.07390 (18)	0.0416 (8)
O5'	0.7029 (2)	0.7376 (3)	0.01133 (17)	0.0365 (7)
O6'	0.8608 (3)	1.1599 (5)	0.1630 (3)	0.0709 (14)
O7'	0.6945 (4)	1.0835 (5)	0.0010 (3)	0.0786 (15)
H7'	0.6713	1.1024	−0.0438	0.094*
O9'	0.6317 (2)	0.8403 (4)	−0.13204 (18)	0.0419 (8)
O10'	0.4893 (3)	0.8760 (4)	−0.2097 (2)	0.0523 (10)
C1	0.6569 (3)	0.6347 (5)	0.1484 (2)	0.0341 (9)
H1A	0.6198	0.6082	0.0979	0.041*
C2	0.5860 (3)	0.6720 (4)	0.1963 (2)	0.0307 (9)
H2A	0.5396	0.6013	0.1964	0.037*
C3	0.6365 (3)	0.7003 (4)	0.2757 (2)	0.0291 (8)
H3A	0.6738	0.7804	0.2778	0.035*
C4	0.7035 (3)	0.5931 (4)	0.3073 (2)	0.0330 (9)
H4A	0.6661	0.5166	0.3154	0.040*
C5	0.7711 (3)	0.5646 (4)	0.2541 (3)	0.0366 (10)
H5A	0.8095	0.6420	0.2496	0.044*
C6	0.4370 (4)	0.7738 (5)	0.1400 (3)	0.0480 (12)
C7	0.3908 (4)	0.8953 (6)	0.1077 (4)	0.0510 (13)
C8	0.2936 (5)	0.9037 (9)	0.1286 (4)	0.0697 (18)
H8A	0.3028	0.9066	0.1831	0.084*
H8B	0.2547	0.8299	0.1093	0.084*
H8C	0.2601	0.9800	0.1069	0.084*
C9	0.3736 (5)	0.8889 (7)	0.0222 (4)	0.0662 (17)
H9A	0.3335	0.8155	0.0040	0.079*
H9B	0.4357	0.8817	0.0074	0.079*
H9C	0.3405	0.9655	0.0005	0.079*
C10	0.4530 (5)	1.0103 (7)	0.1353 (6)	0.083 (2)
H10A	0.4645	1.0149	0.1899	0.099*
H10B	0.4194	1.0865	0.1135	0.099*
H10C	0.5149	1.0033	0.1201	0.099*
C11	0.5675 (4)	0.8081 (5)	0.3659 (3)	0.0425 (11)
C12	0.4819 (4)	0.8150 (5)	0.4036 (3)	0.0442 (11)
C13	0.4973 (7)	0.9324 (8)	0.4537 (5)	0.080 (2)
H13A	0.4435	0.9408	0.4791	0.097*
H13B	0.5001	1.0071	0.4230	0.097*
H13C	0.5580	0.9242	0.4910	0.097*
C14	0.4815 (8)	0.6963 (8)	0.4482 (6)	0.095 (3)
H14A	0.4707	0.6239	0.4143	0.113*
H14B	0.4296	0.7005	0.4758	0.113*
H14C	0.5437	0.6870	0.4835	0.113*
C15	0.3910 (5)	0.8252 (12)	0.3461 (5)	0.097 (3)
H15A	0.3820	0.7490	0.3154	0.116*
H15B	0.3945	0.8985	0.3144	0.116*
H15C	0.3365	0.8350	0.3706	0.116*
C16	0.7530 (4)	0.5863 (6)	0.4416 (3)	0.0487 (12)
C17	0.8293 (4)	0.6325 (7)	0.5069 (3)	0.0627 (17)
C18	0.7842 (13)	0.632 (2)	0.5737 (8)	0.096 (6)*	0.488 (19)
H18A	0.7149	0.6484	0.5578	0.115*	0.488 (19)
H18B	0.8144	0.6966	0.6091	0.115*	0.488 (19)
H18C	0.7940	0.5491	0.5980	0.115*	0.488 (19)
C19	0.9028 (13)	0.5285 (17)	0.5077 (12)	0.105 (7)*	0.488 (19)
H19A	0.9257	0.4982	0.5590	0.126*	0.488 (19)
H19B	0.9574	0.5611	0.4887	0.126*	0.488 (19)
H19C	0.8725	0.4590	0.4760	0.126*	0.488 (19)
C20	0.8723 (16)	0.7568 (14)	0.4923 (13)	0.111 (8)*	0.488 (19)
H20A	0.9428	0.7492	0.5019	0.134*	0.488 (19)
H20B	0.8548	0.8209	0.5254	0.134*	0.488 (19)
H20C	0.8474	0.7813	0.4401	0.134*	0.488 (19)
C18'	0.8185 (13)	0.5609 (16)	0.5761 (8)	0.093 (6)*	0.512 (19)
H18D	0.8800	0.5620	0.6129	0.112*	0.512 (19)
H18E	0.8001	0.4738	0.5626	0.112*	0.512 (19)
H18F	0.7684	0.6007	0.5976	0.112*	0.512 (19)
C19'	0.9275 (10)	0.616 (2)	0.4902 (11)	0.113 (7)*	0.512 (19)
H19D	0.9652	0.5567	0.5261	0.135*	0.512 (19)
H19E	0.9607	0.6972	0.4942	0.135*	0.512 (19)
H19F	0.9208	0.5828	0.4394	0.135*	0.512 (19)
C20'	0.8075 (15)	0.7709 (12)	0.5160 (12)	0.108 (7)*	0.512 (19)
H20D	0.7461	0.7791	0.5317	0.130*	0.512 (19)
H20E	0.8031	0.8143	0.4682	0.130*	0.512 (19)
H20F	0.8594	0.8085	0.5538	0.130*	0.512 (19)
C21	0.8395 (4)	0.4592 (5)	0.2792 (4)	0.0475 (13)
H21A	0.8766	0.4408	0.2406	0.057*
H21B	0.8856	0.4828	0.3259	0.057*
C22	0.8379 (4)	0.2530 (6)	0.3212 (4)	0.0543 (13)
C23	0.7740 (5)	0.1426 (7)	0.3333 (4)	0.0628 (15)
C24	0.8306 (5)	0.0256 (7)	0.3374 (5)	0.0755 (19)
H24A	0.8876	0.0317	0.3785	0.091*
H24B	0.8512	0.0131	0.2902	0.091*
H24C	0.7907	−0.0456	0.3462	0.091*
C25	0.6838 (5)	0.1330 (7)	0.2686 (4)	0.0697 (17)
H25A	0.6434	0.0627	0.2781	0.084*
H25B	0.7040	0.1189	0.2215	0.084*
H25C	0.6468	0.2113	0.2654	0.084*
C26	0.7512 (7)	0.1682 (7)	0.4059 (4)	0.079 (2)
H26A	0.8112	0.1722	0.4444	0.095*
H26B	0.7102	0.1008	0.4182	0.095*
H26C	0.7171	0.2486	0.4039	0.095*
C1'	0.7650 (3)	0.7228 (5)	0.0822 (2)	0.0348 (9)
H1B	0.7928	0.6361	0.0863	0.042*
C2'	0.8466 (3)	0.8183 (5)	0.0922 (2)	0.0360 (10)
H2B	0.8875	0.7984	0.0556	0.043*
C3'	0.8093 (4)	0.9511 (5)	0.0782 (3)	0.0389 (10)
H3B	0.7787	0.9795	0.1196	0.047*
C4'	0.7380 (4)	0.9595 (5)	0.0046 (3)	0.0494 (12)
H4B	0.7714	0.9476	−0.0377	0.059*
C5'	0.6590 (3)	0.8600 (5)	0.0014 (3)	0.0407 (10)
H5B	0.6261	0.8757	0.0435	0.049*
C6'	0.9788 (4)	0.7328 (6)	0.1782 (3)	0.0475 (12)
C7'	1.0517 (4)	0.7576 (6)	0.2509 (3)	0.0496 (12)
C8'	1.0040 (5)	0.7559 (8)	0.3157 (3)	0.0641 (17)
H8D	0.9764	0.6725	0.3199	0.077*
H8E	0.9524	0.8190	0.3081	0.077*
H8F	1.0517	0.7751	0.3616	0.077*
C9'	1.1320 (7)	0.6618 (11)	0.2596 (5)	0.102 (3)
H9D	1.1055	0.5775	0.2628	0.122*
H9E	1.1806	0.6796	0.3052	0.122*
H9F	1.1621	0.6663	0.2163	0.122*
C10'	1.0956 (5)	0.8912 (8)	0.2470 (4)	0.0727 (19)
H10D	1.1436	0.9077	0.2931	0.087*
H10E	1.0441	0.9542	0.2411	0.087*
H10F	1.1266	0.8956	0.2042	0.087*
C11'	0.9055 (4)	1.1359 (6)	0.1166 (3)	0.0473 (12)
C12'	0.9833 (4)	1.2188 (5)	0.0972 (3)	0.0588 (15)
C13'	1.0242 (8)	1.3007 (12)	0.1634 (7)	0.176 (7)
H13D	1.0544	1.2479	0.2058	0.211*
H13E	0.9722	1.3503	0.1767	0.211*
H13F	1.0727	1.3574	0.1507	0.211*
C14'	1.0635 (4)	1.1436 (6)	0.0766 (3)	0.0499 (12)
H14D	1.0370	1.0898	0.0336	0.060*
H14E	1.0944	1.0913	0.1191	0.060*
H14F	1.1114	1.2009	0.0636	0.060*
C15'	0.9351 (6)	1.2964 (10)	0.0313 (7)	0.148 (5)
H15D	0.9087	1.2410	−0.0108	0.178*
H15E	0.9824	1.3535	0.0174	0.178*
H15F	0.8827	1.3455	0.0444	0.178*
C21'	0.5841 (4)	0.8600 (6)	−0.0703 (3)	0.0458 (12)
H21C	0.5366	0.7922	−0.0693	0.055*
H21D	0.5494	0.9414	−0.0764	0.055*
C22'	0.5747 (3)	0.8519 (5)	−0.2007 (3)	0.0369 (9)
C23'	0.6279 (4)	0.8337 (6)	−0.2627 (3)	0.0503 (13)
C24'	0.5545 (7)	0.8239 (16)	−0.3362 (4)	0.118 (4)
H24D	0.5170	0.9019	−0.3452	0.141*
H24E	0.5110	0.7531	−0.3340	0.141*
H24F	0.5881	0.8103	−0.3769	0.141*
C25'	0.6864 (9)	0.7126 (11)	−0.2500 (5)	0.106 (3)
H25D	0.6426	0.6409	−0.2520	0.128*
H25E	0.7306	0.7156	−0.2008	0.128*
H25F	0.7236	0.7036	−0.2888	0.128*
C26'	0.6943 (12)	0.9452 (13)	−0.2626 (8)	0.159 (6)
H26D	0.6561	1.0227	−0.2698	0.191*
H26E	0.7287	0.9360	−0.3033	0.191*
H26F	0.7411	0.9490	−0.2147	0.191*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0353 (15)	0.0345 (15)	0.0298 (14)	−0.0049 (13)	0.0129 (12)	−0.0035 (12)
O2	0.0281 (14)	0.0332 (16)	0.0402 (16)	−0.0030 (12)	0.0074 (13)	0.0037 (13)
O3	0.054 (3)	0.055 (3)	0.132 (5)	−0.017 (2)	−0.016 (3)	0.015 (3)
O4	0.0303 (14)	0.0346 (16)	0.0369 (15)	−0.0032 (12)	0.0171 (12)	−0.0052 (13)
O5	0.0411 (17)	0.0323 (15)	0.0484 (18)	0.0008 (13)	0.0219 (15)	−0.0054 (14)
O6	0.110 (4)	0.082 (4)	0.115 (4)	−0.054 (3)	0.074 (4)	−0.062 (3)
O7	0.0379 (17)	0.0502 (19)	0.0329 (16)	−0.0028 (15)	0.0055 (13)	0.0140 (14)
O8	0.106 (4)	0.120 (5)	0.056 (3)	−0.050 (4)	0.045 (3)	0.005 (3)
O9	0.0374 (17)	0.0312 (16)	0.081 (3)	0.0035 (14)	0.0216 (18)	0.0056 (17)
O10	0.046 (2)	0.054 (2)	0.099 (3)	−0.0004 (19)	−0.001 (2)	0.018 (2)
O2'	0.0305 (15)	0.0496 (19)	0.0310 (15)	−0.0007 (13)	0.0084 (12)	−0.0058 (14)
O3'	0.100 (4)	0.071 (3)	0.055 (2)	0.046 (3)	−0.010 (2)	−0.020 (2)
O4'	0.0407 (17)	0.0478 (19)	0.0410 (17)	−0.0123 (15)	0.0189 (14)	−0.0047 (15)
O5'	0.0347 (16)	0.0432 (17)	0.0317 (15)	−0.0005 (13)	0.0072 (13)	−0.0033 (14)
O6'	0.066 (3)	0.079 (3)	0.080 (3)	−0.023 (2)	0.043 (2)	−0.030 (3)
O7'	0.090 (4)	0.054 (2)	0.077 (3)	0.000 (2)	−0.016 (3)	0.006 (2)
O9'	0.0322 (16)	0.059 (2)	0.0361 (16)	0.0027 (15)	0.0100 (13)	0.0057 (15)
O10'	0.0362 (17)	0.066 (3)	0.050 (2)	0.0009 (17)	−0.0006 (15)	−0.0142 (19)
C1	0.036 (2)	0.037 (2)	0.031 (2)	−0.0076 (18)	0.0119 (17)	−0.0043 (18)
C2	0.029 (2)	0.029 (2)	0.035 (2)	−0.0046 (16)	0.0102 (17)	−0.0009 (17)
C3	0.0289 (19)	0.031 (2)	0.0306 (19)	−0.0017 (16)	0.0142 (16)	−0.0014 (16)
C4	0.030 (2)	0.033 (2)	0.038 (2)	0.0010 (17)	0.0116 (18)	0.0033 (17)
C5	0.034 (2)	0.030 (2)	0.051 (3)	−0.0004 (17)	0.0209 (19)	0.0041 (18)
C6	0.044 (3)	0.049 (3)	0.047 (3)	−0.010 (2)	0.000 (2)	0.002 (2)
C7	0.034 (2)	0.047 (3)	0.069 (3)	−0.002 (2)	0.006 (2)	0.006 (3)
C8	0.053 (3)	0.092 (5)	0.069 (4)	0.001 (3)	0.023 (3)	0.006 (4)
C9	0.072 (4)	0.064 (4)	0.073 (4)	0.014 (3)	0.038 (3)	0.024 (3)
C10	0.051 (3)	0.043 (3)	0.148 (7)	0.003 (3)	0.008 (4)	−0.005 (4)
C11	0.061 (3)	0.029 (2)	0.045 (3)	−0.007 (2)	0.026 (2)	−0.0058 (19)
C12	0.055 (3)	0.047 (3)	0.036 (2)	0.005 (2)	0.021 (2)	−0.001 (2)
C13	0.103 (6)	0.067 (4)	0.083 (5)	0.011 (4)	0.046 (4)	−0.015 (4)
C14	0.126 (7)	0.063 (4)	0.125 (7)	0.008 (4)	0.093 (6)	0.017 (4)
C15	0.062 (4)	0.128 (8)	0.102 (6)	0.020 (5)	0.021 (4)	−0.025 (5)
C16	0.046 (3)	0.060 (3)	0.047 (3)	0.006 (2)	0.025 (2)	0.011 (2)
C17	0.054 (3)	0.096 (5)	0.038 (3)	0.015 (3)	0.011 (2)	0.020 (3)
C21	0.036 (2)	0.038 (2)	0.077 (4)	0.005 (2)	0.030 (2)	0.012 (2)
C22	0.045 (3)	0.044 (3)	0.069 (4)	0.004 (2)	0.003 (3)	0.009 (3)
C23	0.058 (3)	0.052 (3)	0.078 (4)	−0.006 (3)	0.014 (3)	0.010 (3)
C24	0.061 (4)	0.057 (3)	0.102 (5)	−0.005 (3)	0.002 (4)	0.024 (4)
C25	0.054 (3)	0.058 (4)	0.093 (5)	−0.001 (3)	0.007 (3)	0.013 (4)
C26	0.105 (6)	0.052 (4)	0.081 (4)	−0.014 (4)	0.022 (4)	0.002 (3)
C1'	0.038 (2)	0.041 (2)	0.029 (2)	−0.0017 (18)	0.0143 (17)	−0.0022 (18)
C2'	0.035 (2)	0.048 (3)	0.027 (2)	−0.0002 (19)	0.0108 (17)	−0.0010 (19)
C3'	0.038 (2)	0.042 (2)	0.039 (2)	−0.0060 (19)	0.0126 (19)	0.0042 (19)
C4'	0.049 (3)	0.048 (3)	0.048 (3)	−0.002 (2)	0.004 (2)	0.012 (2)
C5'	0.034 (2)	0.050 (3)	0.037 (2)	0.001 (2)	0.0058 (19)	−0.001 (2)
C6'	0.050 (3)	0.053 (3)	0.041 (2)	0.011 (2)	0.014 (2)	0.000 (2)
C7'	0.036 (2)	0.058 (3)	0.054 (3)	0.006 (2)	0.006 (2)	0.001 (3)
C8'	0.059 (3)	0.089 (5)	0.042 (3)	−0.016 (3)	0.007 (2)	0.003 (3)
C9'	0.093 (6)	0.111 (7)	0.085 (5)	0.055 (6)	−0.016 (4)	−0.010 (5)
C10'	0.052 (3)	0.090 (5)	0.071 (4)	−0.022 (3)	0.001 (3)	0.020 (4)
C11'	0.039 (2)	0.055 (3)	0.052 (3)	−0.008 (2)	0.019 (2)	−0.009 (2)
C12'	0.053 (3)	0.044 (3)	0.090 (4)	−0.012 (2)	0.039 (3)	−0.016 (3)
C13'	0.147 (9)	0.197 (13)	0.232 (11)	−0.122 (9)	0.146 (8)	−0.170 (11)
C14'	0.045 (3)	0.053 (3)	0.057 (3)	−0.003 (2)	0.023 (2)	0.010 (2)
C15'	0.074 (5)	0.115 (8)	0.270 (12)	0.033 (5)	0.072 (7)	0.124 (9)
C21'	0.037 (2)	0.066 (3)	0.036 (2)	−0.001 (2)	0.0095 (19)	−0.003 (2)
C22'	0.035 (2)	0.035 (2)	0.039 (2)	−0.0020 (18)	0.0020 (18)	−0.0002 (19)
C23'	0.048 (3)	0.059 (3)	0.047 (3)	0.000 (2)	0.018 (2)	0.014 (3)
C24'	0.091 (6)	0.217 (14)	0.049 (4)	0.007 (7)	0.021 (3)	−0.004 (6)
C25'	0.149 (8)	0.117 (7)	0.072 (5)	0.060 (6)	0.065 (5)	0.012 (5)
C26'	0.223 (13)	0.134 (8)	0.166 (11)	−0.105 (10)	0.143 (10)	−0.048 (8)

Geometric parameters (Å, º) top

O1—C1	1.423 (5)	C20—H20A	0.9800
O1—C1'	1.424 (5)	C20—H20B	0.9800
O2—C6	1.336 (6)	C20—H20C	0.9800
O2—C2	1.445 (5)	C18'—H18D	0.9800
O3—C6	1.199 (7)	C18'—H18E	0.9800
O4—C11	1.333 (6)	C18'—H18F	0.9800
O4—C3	1.451 (5)	C19'—H19D	0.9800
O5—C1	1.398 (6)	C19'—H19E	0.9800
O5—C5	1.436 (6)	C19'—H19F	0.9800
O6—C11	1.200 (7)	C20'—H20D	0.9800
O7—C16	1.351 (6)	C20'—H20E	0.9800
O7—C4	1.450 (6)	C20'—H20F	0.9800
O8—C16	1.190 (8)	C21—H21A	0.9900
O9—C22	1.315 (7)	C21—H21B	0.9900
O9—C21	1.434 (6)	C22—C23	1.528 (9)
O10—C22	1.193 (7)	C23—C26	1.463 (11)
O2'—C6'	1.338 (6)	C23—C24	1.474 (10)
O2'—C2'	1.434 (5)	C23—C25	1.547 (10)
O3'—C6'	1.213 (7)	C24—H24A	0.9800
O4'—C11'	1.353 (7)	C24—H24B	0.9800
O4'—C3'	1.447 (6)	C24—H24C	0.9800
O5'—C1'	1.411 (6)	C25—H25A	0.9800
O5'—C5'	1.439 (6)	C25—H25B	0.9800
O6'—C11'	1.195 (6)	C25—H25C	0.9800
O7'—C4'	1.452 (8)	C26—H26A	0.9800
O7'—H7'	0.8400	C26—H26B	0.9800
O9'—C22'	1.345 (6)	C26—H26C	0.9800
O9'—C21'	1.454 (6)	C1'—C2'	1.521 (6)
O10'—C22'	1.214 (6)	C1'—H1B	1.0000
C1—C2	1.525 (6)	C2'—C3'	1.512 (7)
C1—H1A	1.0000	C2'—H2B	1.0000
C2—C3	1.506 (6)	C3'—C4'	1.502 (7)
C2—H2A	1.0000	C3'—H3B	1.0000
C3—C4	1.517 (6)	C4'—C5'	1.533 (7)
C3—H3A	1.0000	C4'—H4B	1.0000
C4—C5	1.539 (6)	C5'—C21'	1.499 (7)
C4—H4A	1.0000	C5'—H5B	1.0000
C5—C21	1.489 (7)	C6'—C7'	1.521 (8)
C5—H5A	1.0000	C7'—C8'	1.489 (8)
C6—C7	1.511 (8)	C7'—C9'	1.510 (9)
C7—C8	1.513 (8)	C7'—C10'	1.560 (10)
C7—C10	1.528 (9)	C8'—H8D	0.9800
C7—C9	1.536 (9)	C8'—H8E	0.9800
C8—H8A	0.9800	C8'—H8F	0.9800
C8—H8B	0.9800	C9'—H9D	0.9800
C8—H8C	0.9800	C9'—H9E	0.9800
C9—H9A	0.9800	C9'—H9F	0.9800
C9—H9B	0.9800	C10'—H10D	0.9800
C9—H9C	0.9800	C10'—H10E	0.9800
C10—H10A	0.9800	C10'—H10F	0.9800
C10—H10B	0.9800	C11'—C12'	1.513 (7)
C10—H10C	0.9800	C12'—C15'	1.500 (8)
C11—C12	1.524 (7)	C12'—C13'	1.504 (7)
C12—C15	1.480 (10)	C12'—C14'	1.506 (6)
C12—C14	1.506 (9)	C13'—H13D	0.9800
C12—C13	1.537 (9)	C13'—H13E	0.9800
C13—H13A	0.9800	C13'—H13F	0.9800
C13—H13B	0.9800	C14'—H14D	0.9800
C13—H13C	0.9800	C14'—H14E	0.9800
C14—H14A	0.9800	C14'—H14F	0.9800
C14—H14B	0.9800	C15'—H15D	0.9800
C14—H14C	0.9800	C15'—H15E	0.9800
C15—H15A	0.9800	C15'—H15F	0.9800
C15—H15B	0.9800	C21'—H21C	0.9900
C15—H15C	0.9800	C21'—H21D	0.9900
C16—C17	1.511 (9)	C22'—C23'	1.509 (7)
C17—C18	1.500 (10)	C23'—C26'	1.515 (12)
C17—C19'	1.501 (11)	C23'—C24'	1.516 (10)
C17—C20	1.505 (11)	C23'—C25'	1.522 (11)
C17—C18'	1.515 (10)	C24'—H24D	0.9800
C17—C19	1.518 (10)	C24'—H24E	0.9800
C17—C20'	1.521 (11)	C24'—H24F	0.9800
C18—H18A	0.9800	C25'—H25D	0.9800
C18—H18B	0.9800	C25'—H25E	0.9800
C18—H18C	0.9800	C25'—H25F	0.9800
C19—H19A	0.9800	C26'—H26D	0.9800
C19—H19B	0.9800	C26'—H26E	0.9800
C19—H19C	0.9800	C26'—H26F	0.9800

C1—O1—C1'	111.1 (3)	H20D—C20'—H20F	109.5
C6—O2—C2	119.2 (4)	H20E—C20'—H20F	109.5
C11—O4—C3	118.3 (3)	O9—C21—C5	109.1 (4)
C1—O5—C5	112.8 (3)	O9—C21—H21A	109.9
C16—O7—C4	118.7 (4)	C5—C21—H21A	109.9
C22—O9—C21	115.6 (4)	O9—C21—H21B	109.9
C6'—O2'—C2'	116.3 (4)	C5—C21—H21B	109.9
C11'—O4'—C3'	118.7 (4)	H21A—C21—H21B	108.3
C1'—O5'—C5'	112.6 (3)	O10—C22—O9	122.5 (6)
C4'—O7'—H7'	109.5	O10—C22—C23	126.0 (5)
C22'—O9'—C21'	115.4 (4)	O9—C22—C23	111.4 (5)
O5—C1—O1	111.4 (3)	C26—C23—C24	109.7 (7)
O5—C1—C2	110.0 (3)	C26—C23—C22	104.1 (6)
O1—C1—C2	108.3 (4)	C24—C23—C22	108.8 (5)
O5—C1—H1A	109.0	C26—C23—C25	113.6 (6)
O1—C1—H1A	109.0	C24—C23—C25	109.5 (6)
C2—C1—H1A	109.0	C22—C23—C25	111.0 (5)
O2—C2—C3	108.9 (3)	C23—C24—H24A	109.5
O2—C2—C1	109.5 (3)	C23—C24—H24B	109.5
C3—C2—C1	112.0 (3)	H24A—C24—H24B	109.5
O2—C2—H2A	108.8	C23—C24—H24C	109.5
C3—C2—H2A	108.8	H24A—C24—H24C	109.5
C1—C2—H2A	108.8	H24B—C24—H24C	109.5
O4—C3—C2	106.4 (3)	C23—C25—H25A	109.5
O4—C3—C4	109.9 (3)	C23—C25—H25B	109.5
C2—C3—C4	110.2 (3)	H25A—C25—H25B	109.5
O4—C3—H3A	110.1	C23—C25—H25C	109.5
C2—C3—H3A	110.1	H25A—C25—H25C	109.5
C4—C3—H3A	110.1	H25B—C25—H25C	109.5
O7—C4—C3	109.2 (4)	C23—C26—H26A	109.5
O7—C4—C5	104.9 (3)	C23—C26—H26B	109.5
C3—C4—C5	109.4 (4)	H26A—C26—H26B	109.5
O7—C4—H4A	111.1	C23—C26—H26C	109.5
C3—C4—H4A	111.1	H26A—C26—H26C	109.5
C5—C4—H4A	111.1	H26B—C26—H26C	109.5
O5—C5—C21	108.3 (4)	O5'—C1'—O1	111.0 (3)
O5—C5—C4	109.1 (4)	O5'—C1'—C2'	110.0 (4)
C21—C5—C4	113.9 (4)	O1—C1'—C2'	108.2 (3)
O5—C5—H5A	108.4	O5'—C1'—H1B	109.2
C21—C5—H5A	108.4	O1—C1'—H1B	109.2
C4—C5—H5A	108.4	C2'—C1'—H1B	109.2
O3—C6—O2	122.2 (5)	O2'—C2'—C3'	106.6 (4)
O3—C6—C7	124.4 (5)	O2'—C2'—C1'	112.9 (4)
O2—C6—C7	113.4 (4)	C3'—C2'—C1'	112.0 (4)
C6—C7—C8	107.0 (5)	O2'—C2'—H2B	108.4
C6—C7—C10	112.7 (5)	C3'—C2'—H2B	108.4
C8—C7—C10	111.2 (6)	C1'—C2'—H2B	108.4
C6—C7—C9	108.8 (5)	O4'—C3'—C4'	107.7 (4)
C8—C7—C9	108.0 (5)	O4'—C3'—C2'	107.8 (4)
C10—C7—C9	109.0 (6)	C4'—C3'—C2'	110.5 (4)
C7—C8—H8A	109.5	O4'—C3'—H3B	110.3
C7—C8—H8B	109.5	C4'—C3'—H3B	110.3
H8A—C8—H8B	109.5	C2'—C3'—H3B	110.3
C7—C8—H8C	109.5	O7'—C4'—C3'	106.9 (5)
H8A—C8—H8C	109.5	O7'—C4'—C5'	109.0 (5)
H8B—C8—H8C	109.5	C3'—C4'—C5'	109.7 (4)
C7—C9—H9A	109.5	O7'—C4'—H4B	110.4
C7—C9—H9B	109.5	C3'—C4'—H4B	110.4
H9A—C9—H9B	109.5	C5'—C4'—H4B	110.4
C7—C9—H9C	109.5	O5'—C5'—C21'	108.4 (4)
H9A—C9—H9C	109.5	O5'—C5'—C4'	109.2 (4)
H9B—C9—H9C	109.5	C21'—C5'—C4'	114.0 (4)
C7—C10—H10A	109.5	O5'—C5'—H5B	108.4
C7—C10—H10B	109.5	C21'—C5'—H5B	108.4
H10A—C10—H10B	109.5	C4'—C5'—H5B	108.4
C7—C10—H10C	109.5	O3'—C6'—O2'	121.9 (5)
H10A—C10—H10C	109.5	O3'—C6'—C7'	125.7 (5)
H10B—C10—H10C	109.5	O2'—C6'—C7'	112.4 (4)
O6—C11—O4	121.9 (4)	C8'—C7'—C9'	111.8 (6)
O6—C11—C12	124.7 (5)	C8'—C7'—C6'	110.8 (5)
O4—C11—C12	113.2 (4)	C9'—C7'—C6'	109.2 (5)
C15—C12—C14	110.0 (8)	C8'—C7'—C10'	107.6 (6)
C15—C12—C11	109.7 (5)	C9'—C7'—C10'	108.7 (6)
C14—C12—C11	107.7 (5)	C6'—C7'—C10'	108.6 (5)
C15—C12—C13	110.8 (6)	C7'—C8'—H8D	109.5
C14—C12—C13	112.0 (6)	C7'—C8'—H8E	109.5
C11—C12—C13	106.7 (5)	H8D—C8'—H8E	109.5
C12—C13—H13A	109.5	C7'—C8'—H8F	109.5
C12—C13—H13B	109.5	H8D—C8'—H8F	109.5
H13A—C13—H13B	109.5	H8E—C8'—H8F	109.5
C12—C13—H13C	109.5	C7'—C9'—H9D	109.5
H13A—C13—H13C	109.5	C7'—C9'—H9E	109.5
H13B—C13—H13C	109.5	H9D—C9'—H9E	109.5
C12—C14—H14A	109.5	C7'—C9'—H9F	109.5
C12—C14—H14B	109.5	H9D—C9'—H9F	109.5
H14A—C14—H14B	109.5	H9E—C9'—H9F	109.5
C12—C14—H14C	109.5	C7'—C10'—H10D	109.5
H14A—C14—H14C	109.5	C7'—C10'—H10E	109.5
H14B—C14—H14C	109.5	H10D—C10'—H10E	109.5
C12—C15—H15A	109.5	C7'—C10'—H10F	109.5
C12—C15—H15B	109.5	H10D—C10'—H10F	109.5
H15A—C15—H15B	109.5	H10E—C10'—H10F	109.5
C12—C15—H15C	109.5	O6'—C11'—O4'	123.2 (5)
H15A—C15—H15C	109.5	O6'—C11'—C12'	124.7 (5)
H15B—C15—H15C	109.5	O4'—C11'—C12'	112.1 (4)
O8—C16—O7	122.2 (5)	C15'—C12'—C13'	111.0 (8)
O8—C16—C17	126.5 (5)	C15'—C12'—C14'	109.1 (5)
O7—C16—C17	111.3 (5)	C13'—C12'—C14'	109.3 (5)
C18—C17—C19'	138.2 (12)	C15'—C12'—C11'	106.4 (5)
C18—C17—C20	114.4 (9)	C13'—C12'—C11'	108.8 (5)
C19'—C17—C20	68.7 (10)	C14'—C12'—C11'	112.3 (4)
C18—C17—C16	106.7 (9)	C12'—C13'—H13D	109.5
C19'—C17—C16	109.6 (9)	C12'—C13'—H13E	109.5
C20—C17—C16	113.1 (10)	H13D—C13'—H13E	109.5
C18—C17—C18'	34.4 (9)	C12'—C13'—H13F	109.5
C19'—C17—C18'	112.3 (8)	H13D—C13'—H13F	109.5
C20—C17—C18'	135.2 (12)	H13E—C13'—H13F	109.5
C16—C17—C18'	108.4 (9)	C12'—C14'—H14D	109.5
C18—C17—C19	113.7 (8)	C12'—C14'—H14E	109.5
C19'—C17—C19	41.4 (10)	H14D—C14'—H14E	109.5
C20—C17—C19	109.8 (8)	C12'—C14'—H14F	109.5
C16—C17—C19	98.2 (10)	H14D—C14'—H14F	109.5
C18'—C17—C19	79.6 (9)	H14E—C14'—H14F	109.5
C18—C17—C20'	77.5 (10)	C12'—C15'—H15D	109.5
C19'—C17—C20'	110.8 (9)	C12'—C15'—H15E	109.5
C20—C17—C20'	43.0 (9)	H15D—C15'—H15E	109.5
C16—C17—C20'	105.9 (10)	C12'—C15'—H15F	109.5
C18'—C17—C20'	109.6 (8)	H15D—C15'—H15F	109.5
C19—C17—C20'	149.3 (12)	H15E—C15'—H15F	109.5
C17—C18—H18A	109.5	O9'—C21'—C5'	108.8 (4)
C17—C18—H18B	109.5	O9'—C21'—H21C	109.9
H18A—C18—H18B	109.5	C5'—C21'—H21C	109.9
C17—C18—H18C	109.5	O9'—C21'—H21D	109.9
H18A—C18—H18C	109.5	C5'—C21'—H21D	109.9
H18B—C18—H18C	109.5	H21C—C21'—H21D	108.3
C17—C19—H19A	109.5	O10'—C22'—O9'	121.7 (4)
C17—C19—H19B	109.5	O10'—C22'—C23'	124.9 (4)
H19A—C19—H19B	109.5	O9'—C22'—C23'	113.3 (4)
C17—C19—H19C	109.5	C22'—C23'—C26'	108.2 (6)
H19A—C19—H19C	109.5	C22'—C23'—C24'	108.6 (5)
H19B—C19—H19C	109.5	C26'—C23'—C24'	111.2 (9)
C17—C20—H20A	109.5	C22'—C23'—C25'	109.8 (5)
C17—C20—H20B	109.5	C26'—C23'—C25'	110.1 (8)
H20A—C20—H20B	109.5	C24'—C23'—C25'	108.9 (8)
C17—C20—H20C	109.5	C23'—C24'—H24D	109.5
H20A—C20—H20C	109.5	C23'—C24'—H24E	109.5
H20B—C20—H20C	109.5	H24D—C24'—H24E	109.5
C17—C18'—H18D	109.5	C23'—C24'—H24F	109.5
C17—C18'—H18E	109.5	H24D—C24'—H24F	109.5
H18D—C18'—H18E	109.5	H24E—C24'—H24F	109.5
C17—C18'—H18F	109.5	C23'—C25'—H25D	109.5
H18D—C18'—H18F	109.5	C23'—C25'—H25E	109.5
H18E—C18'—H18F	109.5	H25D—C25'—H25E	109.5
C17—C19'—H19D	109.5	C23'—C25'—H25F	109.5
C17—C19'—H19E	109.5	H25D—C25'—H25F	109.5
H19D—C19'—H19E	109.5	H25E—C25'—H25F	109.5
C17—C19'—H19F	109.5	C23'—C26'—H26D	109.5
H19D—C19'—H19F	109.5	C23'—C26'—H26E	109.5
H19E—C19'—H19F	109.5	H26D—C26'—H26E	109.5
C17—C20'—H20D	109.5	C23'—C26'—H26F	109.5
C17—C20'—H20E	109.5	H26D—C26'—H26F	109.5
H20D—C20'—H20E	109.5	H26E—C26'—H26F	109.5
C17—C20'—H20F	109.5

C5—O5—C1—O1	58.8 (4)	O10—C22—C23—C26	91.5 (9)
C5—O5—C1—C2	−61.4 (4)	O9—C22—C23—C26	−85.0 (7)
C1'—O1—C1—O5	73.1 (4)	O10—C22—C23—C24	−25.4 (10)
C1'—O1—C1—C2	−165.8 (3)	O9—C22—C23—C24	158.1 (6)
C6—O2—C2—C3	−120.3 (4)	O10—C22—C23—C25	−145.9 (8)
C6—O2—C2—C1	117.0 (5)	O9—C22—C23—C25	37.5 (8)
O5—C1—C2—O2	175.5 (3)	C5'—O5'—C1'—O1	59.0 (5)
O1—C1—C2—O2	53.5 (4)	C5'—O5'—C1'—C2'	−60.8 (4)
O5—C1—C2—C3	54.7 (5)	C1—O1—C1'—O5'	76.7 (4)
O1—C1—C2—C3	−67.4 (5)	C1—O1—C1'—C2'	−162.5 (4)
C11—O4—C3—C2	−135.9 (4)	C6'—O2'—C2'—C3'	−151.2 (4)
C11—O4—C3—C4	104.9 (4)	C6'—O2'—C2'—C1'	85.4 (5)
O2—C2—C3—O4	68.3 (4)	O5'—C1'—C2'—O2'	174.1 (3)
C1—C2—C3—O4	−170.5 (3)	O1—C1'—C2'—O2'	52.7 (5)
O2—C2—C3—C4	−172.6 (3)	O5'—C1'—C2'—C3'	53.8 (5)
C1—C2—C3—C4	−51.4 (5)	O1—C1'—C2'—C3'	−67.6 (5)
C16—O7—C4—C3	108.2 (5)	C11'—O4'—C3'—C4'	112.2 (5)
C16—O7—C4—C5	−134.6 (4)	C11'—O4'—C3'—C2'	−128.6 (5)
O4—C3—C4—O7	−76.0 (4)	O2'—C2'—C3'—O4'	67.6 (4)
C2—C3—C4—O7	167.1 (3)	C1'—C2'—C3'—O4'	−168.5 (3)
O4—C3—C4—C5	169.7 (3)	O2'—C2'—C3'—C4'	−175.0 (4)
C2—C3—C4—C5	52.8 (4)	C1'—C2'—C3'—C4'	−51.1 (5)
C1—O5—C5—C21	−171.6 (3)	O4'—C3'—C4'—O7'	−71.5 (5)
C1—O5—C5—C4	63.9 (4)	C2'—C3'—C4'—O7'	171.0 (4)
O7—C4—C5—O5	−175.0 (3)	O4'—C3'—C4'—C5'	170.4 (4)
C3—C4—C5—O5	−58.0 (5)	C2'—C3'—C4'—C5'	52.9 (6)
O7—C4—C5—C21	63.8 (5)	C1'—O5'—C5'—C21'	−171.8 (4)
C3—C4—C5—C21	−179.2 (4)	C1'—O5'—C5'—C4'	63.6 (5)
C2—O2—C6—O3	1.2 (8)	O7'—C4'—C5'—O5'	−175.1 (4)
C2—O2—C6—C7	−179.3 (4)	C3'—C4'—C5'—O5'	−58.4 (6)
O3—C6—C7—C8	35.6 (9)	O7'—C4'—C5'—C21'	63.5 (6)
O2—C6—C7—C8	−143.9 (5)	C3'—C4'—C5'—C21'	−179.7 (5)
O3—C6—C7—C10	158.1 (8)	C2'—O2'—C6'—O3'	−13.6 (8)
O2—C6—C7—C10	−21.4 (8)	C2'—O2'—C6'—C7'	166.9 (4)
O3—C6—C7—C9	−80.9 (8)	O3'—C6'—C7'—C8'	−121.1 (7)
O2—C6—C7—C9	99.6 (6)	O2'—C6'—C7'—C8'	58.3 (7)
C3—O4—C11—O6	−8.3 (8)	O3'—C6'—C7'—C9'	2.4 (10)
C3—O4—C11—C12	177.1 (4)	O2'—C6'—C7'—C9'	−178.1 (6)
O6—C11—C12—C15	128.5 (8)	O3'—C6'—C7'—C10'	120.8 (7)
O4—C11—C12—C15	−57.2 (7)	O2'—C6'—C7'—C10'	−59.7 (6)
O6—C11—C12—C14	−111.8 (8)	C3'—O4'—C11'—O6'	7.3 (8)
O4—C11—C12—C14	62.5 (7)	C3'—O4'—C11'—C12'	−171.3 (4)
O6—C11—C12—C13	8.5 (9)	O6'—C11'—C12'—C15'	−95.5 (8)
O4—C11—C12—C13	−177.1 (5)	O4'—C11'—C12'—C15'	83.2 (7)
C4—O7—C16—O8	−3.7 (8)	O6'—C11'—C12'—C13'	24.2 (10)
C4—O7—C16—C17	176.4 (4)	O4'—C11'—C12'—C13'	−157.1 (7)
O8—C16—C17—C18	−27.4 (11)	O6'—C11'—C12'—C14'	145.3 (6)
O7—C16—C17—C18	152.5 (9)	O4'—C11'—C12'—C14'	−36.1 (7)
O8—C16—C17—C19'	131.6 (11)	C22'—O9'—C21'—C5'	−172.9 (4)
O7—C16—C17—C19'	−48.6 (10)	O5'—C5'—C21'—O9'	−63.9 (5)
O8—C16—C17—C20	−153.9 (11)	C4'—C5'—C21'—O9'	57.9 (6)
O7—C16—C17—C20	25.9 (10)	C21'—O9'—C22'—O10'	−0.7 (7)
O8—C16—C17—C18'	8.7 (11)	C21'—O9'—C22'—C23'	178.6 (5)
O7—C16—C17—C18'	−171.4 (8)	O10'—C22'—C23'—C26'	109.4 (10)
O8—C16—C17—C19	90.4 (10)	O9'—C22'—C23'—C26'	−69.9 (9)
O7—C16—C17—C19	−89.7 (9)	O10'—C22'—C23'—C24'	−11.4 (10)
O8—C16—C17—C20'	−108.8 (11)	O9'—C22'—C23'—C24'	169.3 (8)
O7—C16—C17—C20'	71.1 (9)	O10'—C22'—C23'—C25'	−130.4 (7)
C22—O9—C21—C5	−173.8 (5)	O9'—C22'—C23'—C25'	50.3 (8)
O5—C5—C21—O9	−67.2 (5)	C1'—O1—C1—H1A	−47.3
C4—C5—C21—O9	54.5 (6)	C1—O1—C1'—H1B	−43.7
C21—O9—C22—O10	2.7 (10)	H1A—C1—C1'—H1B	−85.3
C21—O9—C22—C23	179.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7′—H7′···O3ⁱ	0.84	2.04	2.868 (8)	169
C2—H2A···O10′ⁱⁱ	1.00	2.45	3.352 (6)	149
C9—H9A···O7′ⁱⁱ	0.98	2.49	3.390 (9)	151
C24—H24C···O6ⁱⁱⁱ	0.98	2.54	3.421 (10)	149

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

Experimental details

Crystal data
Chemical formula	C₄₇H₇₈O₁₈
M_r	931.09
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	150
a, b, c (Å)	14.1855 (3), 10.6390 (2), 18.3343 (4)
β (°)	102.5721 (9)
V (Å³)	2700.66 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.55 × 0.20 × 0.20

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995, 1997)
T_min, T_max	0.954, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	45444, 5812, 4797
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.234, 1.03
No. of reflections	5812
No. of parameters	586
No. of restraints	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.31

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SIR97 (Altomare et al.,1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Selected geometric parameters (Å, º) top

O1—C1	1.423 (5)	O1—C1'	1.424 (5)

C1—O1—C1'	111.1 (3)	C26—C23—C22	104.1 (6)
O8—C16—C17	126.5 (5)

C1'—O1—C1—O5	73.1 (4)	C1—O1—C1'—O5'	76.7 (4)
C1'—O1—C1—C2	−165.8 (3)	C1—O1—C1'—C2'	−162.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7'—H7'···O3ⁱ	.84	2.04	2.868 (8)	169
C2—H2A···O10'ⁱⁱ	1.00	2.45	3.352 (6)	149
C9—H9A···O7'ⁱⁱ	.98	2.49	3.390 (9)	151
C24—H24C···O6ⁱⁱⁱ	.98	2.54	3.421 (10)	149

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

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