O-Benzoyl side-chain conformations in 2,3,4,6-tetra-O-benzoyl-β-d-galacto­pyranosyl-(1→4)-1,2,6-tri-O-benzoyl-β-d-gluco­pyran­ose (ethyl acetate solvate) and 1,2,4,6-tetra-O-benzoyl-β-d-gluco­pyran­ose (acetone solvate)

Turney, T.; Pan, Q.; Zhang, W.; Oliver, A.G.; Serianni, A.S.

doi:10.1107/S2053229619000822

O-Benzoyl side-chain conformations in 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→4)-1,2,6-tri-O-benzoyl-β-D-glucopyranose (ethyl acetate solvate) and 1,2,4,6-tetra-O-benzoyl-β-D-glucopyranose (acetone solvate)

T. Turney, Q. Pan, W. Zhang, A. G. Oliver and A. S. Serianni

The crystal structures of 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→4)-1,2,6-tri-O-benzoyl-β-D-glucopyranose ethyl acetate hemisolvate, C₆₁H₅₀O₁₈·0.5C₄H₈O₂, and 1,2,4,6-tetra-O-benzoyl-β-D-glucopyranose acetone monosolvate, C₃₄H₂₈O₁₀·C₃H₆O, were determined and compared to those of methyl β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside (methyl β-lactoside) and methyl β-D-glucopyranoside hemihydrate, C₇H₁₄O₆·0.5H₂O, to evaluate the effects of O-benzoylation on bond lengths, bond angles and torsion angles. In general, O-benzoylation exerts little effect on exo- and endocyclic C—C and endocyclic C—O bond lengths, but exocyclic C—O bonds involved in O-benzoylation are lengthened by 0.02–0.04 Å depending on the site of substitution. The conformation of the O-benzoyl side-chains is highly conserved, with the carbonyl O atom either eclipsing the H atom attached to a 2°-alcoholic C atom or bisecting the H—C—H bond angle of an 1°-alcoholic C atom. Of the three bonds that determine the side-chain geometry, the C—O bond involving the alcoholic C atom exhibits greater rotational variability than the remaining C—O and C—C bonds involving the carbonyl C atom. These findings are in good agreement with recent solution NMR studies of the O-acetyl side-chain conformation in saccharides.

Keywords: crystal structure; disaccharide; benzoylation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619000822/yf3160sup1.cif Contains datablocks III, IV, V, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619000822/yf3160IIIsup2.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619000822/yf3160IVsup3.hkl Contains datablock IV
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619000822/yf3160Vsup4.hkl Contains datablock V

CCDC references: 1891534; 1891533; 1891532

Computing details top

For all structures, data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

2,3,4,6-Tetra-O-benzoyl-β-D-galactopyranosyl-(1→4)-1,2,6-tri-O-benzoyl-β-D-glucopyranose ethyl acetate hemisolvate (III) top

Crystal data top

2C₆₁H₅₀O₁₈·C₄H₈O₂	F(000) = 2336
M_r = 2230.12	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
a = 23.9979 (5) Å	Cell parameters from 9930 reflections
b = 8.8603 (2) Å	θ = 2.4–57.0°
c = 26.2562 (6) Å	µ = 0.82 mm⁻¹
β = 93.513 (1)°	T = 120 K
V = 5572.3 (2) Å³	Blade, colorless
Z = 2	0.16 × 0.12 × 0.06 mm

Data collection top

Bruker APEXII diffractometer	15912 independent reflections
Radiation source: Incoatec micro-focus	13858 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	R_int = 0.048
combination of ω and φ–scans	θ_max = 59.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −26→26
T_min = 0.634, T_max = 0.752	k = −9→9
68691 measured reflections	l = −28→29

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0638P)² + 2.2199P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
15912 reflections	Δρ_max = 0.46 e Å⁻³
1487 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Absolute structure: Flack x determined using 5615 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: 0.16 (6)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1_1	0.85594 (14)	−0.1830 (4)	0.55659 (15)	0.0371 (9)
O2_1	0.77338 (14)	−0.0691 (4)	0.61459 (14)	0.0372 (9)
O3_1	0.73839 (18)	0.2327 (4)	0.59165 (14)	0.0372 (9)
H3O_1	0.705 (3)	0.238 (7)	0.591 (2)	0.05 (2)*
O5_1	0.83948 (14)	0.0023 (4)	0.49731 (13)	0.0333 (8)
O6_1	0.86665 (15)	0.2680 (4)	0.44280 (14)	0.0357 (9)
O7_1	0.79418 (19)	−0.3742 (5)	0.55047 (17)	0.0585 (12)
O8_1	0.83919 (19)	0.0075 (5)	0.67409 (16)	0.0535 (11)
O9_1	0.8893 (2)	0.2840 (5)	0.36185 (18)	0.0625 (13)
C1_1	0.8144 (2)	−0.0811 (6)	0.5349 (2)	0.0346 (13)
H1_1	0.781619	−0.138652	0.519564	0.042*
C2_1	0.7965 (2)	0.0229 (6)	0.5758 (2)	0.0335 (12)
H2_1	0.829137	0.081692	0.590641	0.040*
C3_1	0.7517 (2)	0.1296 (6)	0.5532 (2)	0.0339 (12)
H3_1	0.717572	0.069903	0.542447	0.041*
C4_1	0.7734 (2)	0.2082 (5)	0.5065 (2)	0.0305 (12)
H4_1	0.802797	0.283331	0.517672	0.037*
C5_1	0.7977 (2)	0.0935 (6)	0.4703 (2)	0.0319 (12)
H5_1	0.766731	0.025429	0.457248	0.038*
C6_1	0.8234 (2)	0.1637 (6)	0.4249 (2)	0.0368 (13)
H6A_1	0.839492	0.083979	0.403873	0.044*
H6B_1	0.794397	0.217748	0.403578	0.044*
O1'_1	0.73017 (14)	0.2818 (4)	0.47550 (13)	0.0335 (8)
O2'_1	0.73105 (14)	0.5826 (4)	0.43640 (13)	0.0345 (8)
O3'_1	0.62427 (14)	0.7234 (4)	0.43493 (13)	0.0350 (9)
O4'_1	0.56144 (14)	0.4847 (3)	0.46937 (13)	0.0311 (8)
O5'_1	0.65583 (14)	0.3411 (4)	0.52118 (13)	0.0311 (8)
O6'_1	0.61436 (15)	0.3033 (4)	0.61635 (14)	0.0374 (9)
O7'_1	0.72748 (17)	0.4454 (5)	0.36413 (15)	0.0481 (10)
O8'_1	0.67386 (16)	0.9196 (4)	0.46755 (15)	0.0402 (9)
O9'_1	0.48860 (17)	0.5924 (6)	0.50503 (18)	0.0628 (13)
O10'_1	0.53380 (18)	0.2183 (4)	0.64377 (16)	0.0510 (11)
C1'_1	0.7035 (2)	0.4011 (5)	0.4971 (2)	0.0301 (12)
H1'_1	0.729188	0.454066	0.522598	0.036*
C2'_1	0.6833 (2)	0.5086 (6)	0.4547 (2)	0.0324 (12)
H2'_1	0.662687	0.452072	0.426411	0.039*
C3'_1	0.6464 (2)	0.6283 (5)	0.4757 (2)	0.0323 (12)
H3'_1	0.670113	0.692456	0.499744	0.039*
C4'_1	0.5996 (2)	0.5653 (5)	0.5047 (2)	0.0334 (12)
H4'_1	0.579438	0.648884	0.521371	0.040*
C5'_1	0.6245 (2)	0.4569 (5)	0.5450 (2)	0.0294 (12)
H5'_1	0.650381	0.514701	0.569007	0.035*
C6'_1	0.5823 (2)	0.3788 (6)	0.5752 (2)	0.0334 (12)
H6'A_1	0.556095	0.452513	0.588850	0.040*
H6'B_1	0.560734	0.304687	0.553715	0.040*
C7_1	0.8382 (2)	−0.3261 (6)	0.5667 (2)	0.0384 (13)
C8_1	0.8788 (2)	−0.4079 (6)	0.6012 (2)	0.0367 (13)
C9_1	0.9317 (2)	−0.3514 (7)	0.6153 (3)	0.0499 (16)
H9_1	0.943922	−0.259435	0.601113	0.060*
C10_1	0.9663 (3)	−0.4292 (7)	0.6499 (3)	0.0639 (19)
H10_1	1.002480	−0.391074	0.659121	0.077*
C11_1	0.9489 (3)	−0.5617 (8)	0.6712 (3)	0.0624 (19)
H11_1	0.972746	−0.613366	0.695648	0.075*
C12_1	0.8960 (3)	−0.6203 (7)	0.6568 (3)	0.0536 (17)
H12_1	0.883995	−0.712504	0.670992	0.064*
C13_1	0.8614 (3)	−0.5430 (6)	0.6219 (2)	0.0439 (14)
H13_1	0.825601	−0.582438	0.611934	0.053*
C14_1	0.8024 (2)	−0.0788 (6)	0.6603 (2)	0.0394 (13)
C15_1	0.7837 (2)	−0.2085 (6)	0.6912 (2)	0.0392 (13)
C16_1	0.7452 (2)	−0.3132 (6)	0.6714 (2)	0.0435 (14)
H16_1	0.729457	−0.302883	0.637459	0.052*
C17_1	0.7301 (3)	−0.4318 (7)	0.7011 (3)	0.0546 (17)
H17_1	0.703553	−0.503189	0.687660	0.065*
C18_1	0.7529 (3)	−0.4491 (9)	0.7503 (3)	0.065 (2)
H18_1	0.741592	−0.531071	0.770585	0.078*
C19_1	0.7919 (3)	−0.3476 (9)	0.7700 (3)	0.0648 (19)
H19_1	0.807953	−0.359664	0.803773	0.078*
C20_1	0.8076 (3)	−0.2278 (7)	0.7403 (2)	0.0514 (16)
H20_1	0.834841	−0.158200	0.753520	0.062*
C21_1	0.8981 (2)	0.3198 (6)	0.4058 (2)	0.0401 (14)
C22_1	0.9441 (2)	0.4236 (6)	0.4252 (2)	0.0380 (14)
C23_1	0.9504 (3)	0.4662 (6)	0.4749 (2)	0.0476 (15)
H23_1	0.924401	0.433810	0.498471	0.057*
C24_1	0.9957 (3)	0.5590 (8)	0.4911 (3)	0.0647 (19)
H24_1	1.001254	0.588553	0.525785	0.078*
C25_1	1.0322 (3)	0.6064 (8)	0.4551 (3)	0.067 (2)
H25_1	1.062763	0.669859	0.465490	0.081*
C26_1	1.0251 (3)	0.5637 (7)	0.4056 (3)	0.0587 (19)
H26_1	1.050612	0.596950	0.381685	0.070*
C27_1	0.9805 (2)	0.4712 (7)	0.3898 (3)	0.0508 (16)
H27_1	0.975177	0.441215	0.355087	0.061*
C7'_1	0.7499 (2)	0.5406 (6)	0.3912 (2)	0.0348 (13)
C8'_1	0.8010 (2)	0.6246 (6)	0.3790 (2)	0.0355 (13)
C9'_1	0.8323 (2)	0.7036 (6)	0.4160 (2)	0.0402 (14)
H9'_1	0.821216	0.706046	0.450124	0.048*
C10'_1	0.8803 (2)	0.7796 (6)	0.4032 (3)	0.0471 (15)
H10'_1	0.901849	0.833501	0.428689	0.056*
C11'_1	0.8966 (3)	0.7775 (6)	0.3544 (3)	0.0512 (17)
H11'_1	0.929198	0.830107	0.345904	0.061*
C12'_1	0.8654 (3)	0.6986 (8)	0.3175 (3)	0.0620 (19)
H12'_1	0.876562	0.697434	0.283359	0.074*
C13'_1	0.8183 (3)	0.6215 (7)	0.3297 (2)	0.0516 (16)
H13'_1	0.797481	0.565814	0.304165	0.062*
C14'_1	0.6428 (2)	0.8685 (6)	0.4347 (2)	0.0324 (12)
C15'_1	0.6197 (2)	0.9520 (6)	0.3890 (2)	0.0351 (13)
C16'_1	0.5828 (3)	0.8875 (6)	0.3525 (2)	0.0456 (15)
H16'_1	0.570275	0.786773	0.356763	0.055*
C17'_1	0.5640 (3)	0.9688 (7)	0.3100 (2)	0.0536 (17)
H17'_1	0.538462	0.924581	0.285251	0.064*
C18'_1	0.5828 (3)	1.1154 (7)	0.3035 (2)	0.0520 (17)
H18'_1	0.570467	1.171437	0.274068	0.062*
C19'_1	0.6193 (3)	1.1793 (7)	0.3400 (3)	0.0572 (18)
H19'_1	0.632038	1.279643	0.335497	0.069*
C20'_1	0.6375 (2)	1.1000 (6)	0.3826 (2)	0.0454 (15)
H20'_1	0.662111	1.145933	0.407680	0.055*
C21'_1	0.5058 (2)	0.5101 (6)	0.4733 (2)	0.0354 (13)
C22'_1	0.4705 (2)	0.4251 (6)	0.4357 (2)	0.0326 (12)
C23'_1	0.4927 (2)	0.3260 (6)	0.4010 (2)	0.0354 (13)
H23'_1	0.531828	0.309811	0.401391	0.042*
C24'_1	0.4568 (2)	0.2508 (7)	0.3656 (2)	0.0426 (14)
H24'_1	0.471331	0.183079	0.341698	0.051*
C25'_1	0.3992 (2)	0.2759 (6)	0.3657 (2)	0.0429 (14)
H25'_1	0.374593	0.225708	0.341505	0.051*
C26'_1	0.3781 (2)	0.3722 (6)	0.4003 (2)	0.0388 (14)
H26'_1	0.338961	0.387367	0.400405	0.047*
C27'_1	0.4131 (2)	0.4472 (6)	0.4350 (2)	0.0360 (13)
H27'_1	0.397985	0.514637	0.458737	0.043*
C28'_1	0.5837 (2)	0.2266 (5)	0.6490 (2)	0.0368 (13)
C29'_1	0.6191 (3)	0.1500 (6)	0.6908 (2)	0.0387 (14)
C30'_1	0.6760 (3)	0.1684 (6)	0.6974 (2)	0.0424 (14)
H30'_1	0.695045	0.230294	0.674589	0.051*
C31'_1	0.7052 (3)	0.0968 (7)	0.7371 (2)	0.0540 (17)
H31'_1	0.744369	0.111864	0.742268	0.065*
C32'_1	0.6780 (3)	0.0035 (7)	0.7693 (3)	0.0576 (18)
H32'_1	0.698680	−0.048336	0.795927	0.069*
C33'_1	0.6219 (3)	−0.0148 (7)	0.7633 (2)	0.0554 (18)
H33'_1	0.603162	−0.076702	0.786310	0.066*
C34'_1	0.5918 (3)	0.0569 (6)	0.7234 (2)	0.0463 (15)
H34'_1	0.552642	0.042074	0.718573	0.056*
O1_2	0.84604 (14)	0.2635 (4)	0.07633 (14)	0.0372 (9)
O2_2	0.75556 (15)	0.3668 (4)	0.12666 (14)	0.0362 (9)
O3_2	0.72191 (18)	0.6747 (4)	0.10155 (15)	0.0373 (9)
H3O_2	0.694 (3)	0.693 (8)	0.091 (2)	0.05 (2)*
O5_2	0.83283 (14)	0.4445 (4)	0.01627 (14)	0.0346 (8)
O6_2	0.86187 (14)	0.6982 (4)	−0.04511 (14)	0.0355 (9)
O7_2	0.78722 (19)	0.0664 (4)	0.06455 (16)	0.0526 (11)
O8_2	0.7913 (2)	0.4889 (5)	0.19624 (16)	0.0572 (12)
O9_2	0.88717 (18)	0.6898 (5)	−0.12596 (16)	0.0544 (11)
C1_2	0.8051 (2)	0.3589 (5)	0.0525 (2)	0.0327 (12)
H1_2	0.774381	0.297845	0.035271	0.039*
C2_2	0.7819 (2)	0.4649 (5)	0.0916 (2)	0.0320 (12)
H2_2	0.812649	0.523992	0.109682	0.038*
C3_2	0.7400 (2)	0.5692 (5)	0.0646 (2)	0.0307 (12)
H3_2	0.707218	0.508554	0.051119	0.037*
C4_2	0.7663 (2)	0.6480 (6)	0.0200 (2)	0.0326 (12)
H4_2	0.795383	0.721218	0.033243	0.039*
C5_2	0.7923 (2)	0.5314 (5)	−0.0140 (2)	0.0320 (12)
H5_2	0.761942	0.460475	−0.026164	0.038*
C6_2	0.8185 (2)	0.5899 (6)	−0.0602 (2)	0.0337 (12)
H6C_2	0.834769	0.505153	−0.078886	0.040*
H6D_2	0.789719	0.638969	−0.083259	0.040*
O2'_2	0.73415 (14)	1.0263 (4)	−0.05267 (13)	0.0330 (8)
O3'_2	0.62946 (15)	1.1682 (4)	−0.06736 (14)	0.0363 (9)
O1'_2	0.72620 (14)	0.7235 (4)	−0.01375 (13)	0.0315 (8)
O4'_2	0.56165 (14)	0.9299 (4)	−0.03920 (14)	0.0335 (8)
O5'_2	0.64768 (13)	0.7910 (3)	0.02464 (13)	0.0305 (8)
O6'_2	0.59142 (14)	0.7601 (4)	0.11354 (14)	0.0362 (9)
O7'_2	0.73943 (17)	0.8832 (4)	−0.12360 (15)	0.0461 (10)
O8'_2	0.66683 (16)	1.3712 (4)	−0.02683 (15)	0.0414 (10)
O9'_2	0.48279 (15)	1.0124 (4)	−0.00685 (16)	0.0441 (10)
O10'_2	0.50621 (17)	0.6740 (4)	0.12857 (16)	0.0464 (10)
C1'_2	0.6981 (2)	0.8465 (5)	0.0051 (2)	0.0303 (12)
H1'_2	0.721628	0.899199	0.032347	0.036*
C2'_2	0.6836 (2)	0.9521 (5)	−0.0395 (2)	0.0322 (12)
H2'_2	0.666308	0.895128	−0.069305	0.039*
C3'_2	0.6450 (2)	1.0771 (5)	−0.0233 (2)	0.0302 (12)
H3'_2	0.665622	1.141660	0.002780	0.036*
C4'_2	0.5938 (2)	1.0136 (5)	−0.0005 (2)	0.0327 (12)
H4'_2	0.570781	1.097410	0.012625	0.039*
C5'_2	0.6133 (2)	0.9093 (5)	0.0432 (2)	0.0320 (12)
H5'_2	0.635638	0.969146	0.069440	0.038*
C6'_2	0.5662 (2)	0.8321 (6)	0.0682 (2)	0.0338 (12)
H6'C_2	0.537723	0.906560	0.077421	0.041*
H6'D_2	0.548122	0.756185	0.044966	0.041*
C7_2	0.8306 (3)	0.1151 (6)	0.0813 (2)	0.0399 (14)
C8_2	0.8749 (3)	0.0234 (6)	0.1097 (2)	0.0399 (14)
C9_2	0.9289 (3)	0.0734 (7)	0.1183 (2)	0.0487 (16)
H9_2	0.939464	0.170079	0.106613	0.058*
C10_2	0.9680 (3)	−0.0190 (7)	0.1444 (3)	0.0563 (18)
H10_2	1.005705	0.013456	0.149538	0.068*
C11_2	0.9523 (3)	−0.1567 (7)	0.1626 (3)	0.0530 (17)
H11_2	0.979103	−0.218361	0.180801	0.064*
C12_2	0.8984 (3)	−0.2062 (6)	0.1549 (2)	0.0478 (16)
H12_2	0.887835	−0.301588	0.167774	0.057*
C13_2	0.8589 (3)	−0.1162 (6)	0.1280 (2)	0.0448 (15)
H13_2	0.821458	−0.149996	0.122320	0.054*
C14_2	0.7682 (3)	0.3798 (6)	0.1767 (2)	0.0419 (14)
C15_2	0.7510 (2)	0.2431 (6)	0.2057 (2)	0.0421 (14)
C16_2	0.7379 (2)	0.1106 (7)	0.1814 (2)	0.0453 (15)
H16_2	0.736603	0.105926	0.145234	0.054*
C17_2	0.7264 (3)	−0.0167 (7)	0.2093 (3)	0.0549 (17)
H17_2	0.717776	−0.109057	0.192165	0.066*
C18_2	0.7276 (3)	−0.0102 (8)	0.2617 (3)	0.0603 (18)
H18_2	0.720406	−0.098485	0.280807	0.072*
C19_2	0.7389 (3)	0.1229 (8)	0.2864 (3)	0.068 (2)
H19_2	0.738260	0.128164	0.322490	0.081*
C20_2	0.7515 (3)	0.2512 (8)	0.2585 (3)	0.0579 (17)
H20_2	0.760363	0.343434	0.275548	0.070*
C21_2	0.8943 (2)	0.7377 (6)	−0.0832 (2)	0.0342 (13)
C22_2	0.9409 (2)	0.8404 (6)	−0.0658 (2)	0.0367 (13)
C23_2	0.9492 (2)	0.8934 (6)	−0.0167 (2)	0.0424 (14)
H23_2	0.923454	0.867660	0.007982	0.051*
C24_2	0.9949 (3)	0.9843 (7)	−0.0027 (3)	0.0476 (15)
H24_2	1.001163	1.018654	0.031418	0.057*
C25_2	1.0311 (3)	1.0237 (6)	−0.0395 (3)	0.0492 (16)
H25_2	1.062235	1.086339	−0.030327	0.059*
C26_2	1.0231 (3)	0.9750 (7)	−0.0885 (3)	0.0517 (16)
H26_2	1.048343	1.003658	−0.113264	0.062*
C27_2	0.9779 (2)	0.8832 (7)	−0.1021 (2)	0.0450 (15)
H27_2	0.972048	0.849263	−0.136289	0.054*
C7'_2	0.7581 (2)	0.9813 (6)	−0.0953 (2)	0.0357 (13)
C8'_2	0.8099 (2)	1.0702 (6)	−0.1026 (2)	0.0400 (14)
C9'_2	0.8383 (2)	1.1442 (6)	−0.0632 (3)	0.0450 (15)
H9'_2	0.824807	1.139890	−0.029937	0.054*
C10'_2	0.8863 (3)	1.2252 (6)	−0.0712 (3)	0.062 (2)
H10'_2	0.906389	1.274716	−0.043732	0.075*
C11'_2	0.9043 (3)	1.2325 (8)	−0.1197 (4)	0.082 (3)
H11'_2	0.936668	1.289662	−0.125899	0.099*
C12'_2	0.8764 (4)	1.1586 (9)	−0.1593 (4)	0.089 (3)
H12'_2	0.889684	1.164618	−0.192620	0.107*
C13'_2	0.8293 (3)	1.0759 (7)	−0.1513 (3)	0.064 (2)
H13'_2	0.810251	1.023271	−0.178646	0.077*
C14'_2	0.6453 (2)	1.3151 (6)	−0.0647 (2)	0.0328 (12)
C15'_2	0.6330 (2)	1.3953 (6)	−0.1136 (2)	0.0338 (13)
C16'_2	0.6052 (2)	1.3274 (6)	−0.1553 (2)	0.0363 (13)
H16'_2	0.593069	1.225654	−0.153276	0.044*
C17'_2	0.5951 (3)	1.4085 (6)	−0.2001 (2)	0.0445 (15)
H17'_2	0.574988	1.363437	−0.228424	0.053*
C18'_2	0.6144 (3)	1.5559 (6)	−0.2033 (2)	0.0472 (15)
H18'_2	0.608488	1.610644	−0.234286	0.057*
C19'_2	0.6423 (2)	1.6229 (6)	−0.1615 (2)	0.0462 (15)
H19'_2	0.654971	1.724154	−0.163711	0.055*
C20'_2	0.6517 (2)	1.5443 (6)	−0.1169 (2)	0.0380 (13)
H20'_2	0.670772	1.590784	−0.088292	0.046*
C21'_2	0.5056 (2)	0.9384 (6)	−0.0379 (2)	0.0379 (13)
C22'_2	0.4760 (2)	0.8449 (6)	−0.0783 (2)	0.0363 (13)
C23'_2	0.5034 (2)	0.7502 (7)	−0.1100 (2)	0.0466 (15)
H23'_2	0.542897	0.741865	−0.106541	0.056*
C24'_2	0.4731 (3)	0.6672 (7)	−0.1467 (3)	0.0554 (17)
H24'_2	0.491944	0.600601	−0.168261	0.067*
C25'_2	0.4157 (3)	0.6807 (8)	−0.1523 (3)	0.0572 (18)
H25'_2	0.395260	0.625351	−0.178141	0.069*
C26'_2	0.3881 (2)	0.7745 (7)	−0.1203 (2)	0.0486 (16)
H26'_2	0.348538	0.781427	−0.123717	0.058*
C27'_2	0.4177 (2)	0.8593 (7)	−0.0829 (2)	0.0428 (14)
H27'_2	0.398845	0.925019	−0.061106	0.051*
C28'_2	0.5546 (2)	0.6892 (6)	0.1420 (2)	0.0348 (13)
C29'_2	0.5813 (2)	0.6338 (6)	0.1918 (2)	0.0374 (13)
C30'_2	0.6382 (3)	0.6363 (6)	0.2025 (2)	0.0437 (14)
H30'_2	0.662477	0.666165	0.177122	0.052*
C31'_2	0.6597 (3)	0.5948 (7)	0.2506 (2)	0.0493 (16)
H31'_2	0.698921	0.593118	0.257896	0.059*
C32'_2	0.6245 (3)	0.5562 (7)	0.2877 (3)	0.0557 (17)
H32'_2	0.639372	0.532260	0.321087	0.067*
C33'_2	0.5675 (3)	0.5520 (9)	0.2767 (3)	0.068 (2)
H33'_2	0.543078	0.523846	0.302163	0.082*
C34'_2	0.5467 (3)	0.5887 (8)	0.2287 (2)	0.0555 (17)
H34'_2	0.507569	0.582889	0.220660	0.067*
O1S_3	0.9572 (3)	0.5093 (7)	0.2217 (2)	0.0971 (19)
O2S_3	0.9617 (2)	0.2776 (6)	0.25283 (19)	0.0678 (13)
C1S_3	1.0440 (3)	0.4157 (14)	0.2566 (4)	0.109 (4)
H1SA_3	1.064301	0.445529	0.226973	0.164*
H1SB_3	1.057012	0.316195	0.268587	0.164*
H1SC_3	1.050817	0.489858	0.284009	0.164*
C2S_3	0.9847 (3)	0.4089 (10)	0.2424 (3)	0.072 (2)
C3S_3	0.9022 (3)	0.2583 (8)	0.2396 (3)	0.0619 (19)
H3SA_3	0.894147	0.271514	0.202423	0.074*
H3SB_3	0.880162	0.333027	0.257861	0.074*
C4S_3	0.8879 (3)	0.0979 (8)	0.2558 (3)	0.0653 (19)
H4SA_3	0.848624	0.076701	0.245812	0.098*
H4SB_3	0.894026	0.088477	0.292893	0.098*
H4SC_3	0.911728	0.025820	0.239047	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1_1	0.028 (2)	0.0242 (19)	0.059 (3)	−0.0011 (15)	−0.0023 (18)	0.0011 (16)
O2_1	0.033 (2)	0.040 (2)	0.038 (2)	−0.0008 (16)	−0.0048 (18)	0.0034 (17)
O3_1	0.033 (2)	0.040 (2)	0.039 (2)	0.0109 (18)	0.0039 (19)	−0.0010 (16)
O5_1	0.030 (2)	0.0254 (18)	0.045 (2)	0.0023 (15)	0.0042 (17)	−0.0014 (16)
O6_1	0.035 (2)	0.031 (2)	0.042 (2)	−0.0045 (16)	0.0030 (17)	−0.0010 (16)
O7_1	0.055 (3)	0.045 (3)	0.073 (3)	−0.022 (2)	−0.022 (2)	0.007 (2)
O8_1	0.064 (3)	0.038 (2)	0.056 (3)	−0.011 (2)	−0.017 (2)	0.0018 (19)
O9_1	0.075 (3)	0.064 (3)	0.050 (3)	−0.026 (2)	0.020 (2)	−0.008 (2)
C1_1	0.020 (3)	0.032 (3)	0.050 (4)	0.002 (2)	−0.004 (2)	−0.001 (2)
C2_1	0.028 (3)	0.029 (3)	0.043 (3)	−0.001 (2)	0.000 (2)	0.008 (2)
C3_1	0.021 (3)	0.041 (3)	0.040 (3)	−0.001 (2)	−0.002 (2)	−0.001 (2)
C4_1	0.023 (3)	0.025 (3)	0.042 (3)	0.001 (2)	−0.004 (2)	0.000 (2)
C5_1	0.029 (3)	0.026 (3)	0.041 (3)	−0.001 (2)	−0.004 (2)	−0.003 (2)
C6_1	0.036 (3)	0.040 (3)	0.035 (3)	−0.002 (2)	0.003 (3)	−0.003 (2)
O1'_1	0.029 (2)	0.033 (2)	0.038 (2)	−0.0003 (15)	−0.0028 (16)	−0.0013 (16)
O2'_1	0.031 (2)	0.034 (2)	0.038 (2)	−0.0088 (15)	0.0003 (17)	0.0007 (16)
O3'_1	0.036 (2)	0.0264 (19)	0.041 (2)	−0.0058 (15)	−0.0106 (17)	0.0066 (15)
O4'_1	0.023 (2)	0.0243 (18)	0.045 (2)	−0.0032 (14)	−0.0028 (16)	−0.0010 (15)
O5'_1	0.029 (2)	0.0234 (18)	0.041 (2)	0.0010 (14)	0.0034 (16)	0.0021 (15)
O6'_1	0.039 (2)	0.032 (2)	0.041 (2)	0.0038 (16)	0.0050 (18)	0.0092 (16)
O7'_1	0.048 (3)	0.055 (3)	0.042 (2)	−0.011 (2)	0.002 (2)	−0.006 (2)
O8'_1	0.044 (2)	0.026 (2)	0.049 (2)	−0.0056 (17)	−0.008 (2)	0.0011 (17)
O9'_1	0.035 (3)	0.077 (3)	0.076 (3)	0.010 (2)	0.000 (2)	−0.036 (3)
O10'_1	0.042 (3)	0.049 (3)	0.063 (3)	0.0031 (19)	0.018 (2)	0.017 (2)
C1'_1	0.024 (3)	0.025 (3)	0.042 (3)	−0.002 (2)	0.005 (2)	−0.004 (2)
C2'_1	0.030 (3)	0.030 (3)	0.037 (3)	−0.010 (2)	−0.002 (2)	−0.001 (2)
C3'_1	0.032 (3)	0.026 (3)	0.038 (3)	−0.005 (2)	−0.007 (2)	0.003 (2)
C4'_1	0.036 (3)	0.024 (3)	0.039 (3)	0.004 (2)	−0.005 (3)	−0.001 (2)
C5'_1	0.028 (3)	0.020 (3)	0.040 (3)	0.004 (2)	−0.001 (2)	−0.001 (2)
C6'_1	0.030 (3)	0.026 (3)	0.044 (3)	0.006 (2)	−0.001 (3)	0.006 (2)
C7_1	0.042 (4)	0.030 (3)	0.043 (3)	−0.004 (3)	0.004 (3)	−0.004 (2)
C8_1	0.034 (3)	0.023 (3)	0.052 (4)	0.003 (2)	0.002 (3)	−0.007 (2)
C9_1	0.041 (4)	0.031 (3)	0.076 (5)	0.005 (3)	−0.005 (3)	0.002 (3)
C10_1	0.053 (4)	0.040 (4)	0.096 (6)	−0.002 (3)	−0.014 (4)	−0.003 (4)
C11_1	0.051 (4)	0.051 (4)	0.083 (5)	0.009 (3)	−0.015 (4)	0.002 (4)
C12_1	0.050 (4)	0.035 (3)	0.076 (5)	0.010 (3)	0.002 (3)	0.011 (3)
C13_1	0.040 (4)	0.036 (3)	0.056 (4)	0.006 (3)	0.003 (3)	−0.007 (3)
C14_1	0.043 (4)	0.033 (3)	0.041 (4)	0.007 (3)	−0.005 (3)	−0.002 (3)
C15_1	0.039 (3)	0.040 (3)	0.039 (3)	0.002 (3)	0.003 (3)	0.002 (2)
C16_1	0.039 (3)	0.045 (3)	0.046 (4)	0.001 (3)	0.000 (3)	0.005 (3)
C17_1	0.049 (4)	0.056 (4)	0.059 (4)	0.001 (3)	0.005 (3)	0.011 (3)
C18_1	0.058 (5)	0.070 (5)	0.066 (5)	0.006 (4)	0.009 (4)	0.025 (4)
C19_1	0.065 (5)	0.080 (5)	0.048 (4)	0.000 (4)	−0.004 (4)	0.011 (4)
C20_1	0.058 (4)	0.048 (4)	0.046 (4)	−0.003 (3)	−0.008 (3)	0.007 (3)
C21_1	0.040 (3)	0.039 (3)	0.042 (4)	0.005 (3)	0.013 (3)	0.004 (3)
C22_1	0.030 (3)	0.026 (3)	0.058 (4)	0.004 (2)	0.007 (3)	0.005 (3)
C23_1	0.047 (4)	0.041 (3)	0.055 (4)	−0.005 (3)	−0.003 (3)	0.000 (3)
C24_1	0.062 (5)	0.054 (4)	0.076 (5)	−0.014 (4)	−0.011 (4)	−0.005 (4)
C25_1	0.039 (4)	0.046 (4)	0.116 (7)	−0.009 (3)	−0.001 (4)	0.000 (4)
C26_1	0.033 (4)	0.038 (4)	0.107 (6)	−0.007 (3)	0.017 (4)	−0.002 (4)
C27_1	0.041 (4)	0.041 (4)	0.072 (5)	0.006 (3)	0.013 (3)	0.003 (3)
C7'_1	0.039 (3)	0.028 (3)	0.037 (3)	−0.003 (2)	−0.002 (3)	0.002 (2)
C8'_1	0.034 (3)	0.029 (3)	0.044 (3)	0.000 (2)	0.006 (3)	0.002 (2)
C9'_1	0.037 (3)	0.029 (3)	0.055 (4)	−0.002 (2)	0.008 (3)	−0.003 (3)
C10'_1	0.036 (3)	0.030 (3)	0.077 (5)	−0.005 (2)	0.011 (3)	−0.002 (3)
C11'_1	0.044 (4)	0.032 (3)	0.079 (5)	−0.001 (3)	0.018 (4)	0.012 (3)
C12'_1	0.063 (5)	0.063 (4)	0.063 (5)	−0.006 (4)	0.027 (4)	0.003 (4)
C13'_1	0.054 (4)	0.049 (4)	0.053 (4)	−0.012 (3)	0.010 (3)	0.000 (3)
C14'_1	0.029 (3)	0.024 (3)	0.045 (3)	−0.004 (2)	0.005 (3)	−0.001 (2)
C15'_1	0.032 (3)	0.032 (3)	0.041 (3)	−0.005 (2)	0.002 (3)	0.008 (2)
C16'_1	0.049 (4)	0.030 (3)	0.057 (4)	−0.014 (3)	−0.010 (3)	0.007 (3)
C17'_1	0.052 (4)	0.052 (4)	0.054 (4)	−0.008 (3)	−0.017 (3)	0.013 (3)
C18'_1	0.052 (4)	0.049 (4)	0.053 (4)	−0.007 (3)	−0.004 (3)	0.020 (3)
C19'_1	0.067 (5)	0.034 (3)	0.070 (5)	−0.015 (3)	−0.001 (4)	0.016 (3)
C20'_1	0.047 (4)	0.030 (3)	0.057 (4)	−0.017 (3)	−0.007 (3)	0.009 (3)
C21'_1	0.029 (3)	0.023 (3)	0.054 (4)	−0.002 (2)	0.000 (3)	0.001 (3)
C22'_1	0.031 (3)	0.027 (3)	0.040 (3)	−0.003 (2)	0.001 (2)	0.006 (2)
C23'_1	0.025 (3)	0.028 (3)	0.053 (4)	−0.004 (2)	−0.004 (3)	0.004 (2)
C24'_1	0.038 (4)	0.042 (3)	0.047 (4)	−0.007 (3)	0.002 (3)	0.000 (3)
C25'_1	0.033 (3)	0.040 (3)	0.053 (4)	−0.008 (3)	−0.012 (3)	0.005 (3)
C26'_1	0.031 (3)	0.034 (3)	0.051 (4)	−0.004 (2)	0.002 (3)	0.009 (3)
C27'_1	0.029 (3)	0.029 (3)	0.050 (4)	0.001 (2)	0.000 (3)	0.006 (2)
C28'_1	0.040 (4)	0.023 (3)	0.049 (4)	0.004 (2)	0.015 (3)	0.003 (2)
C29'_1	0.061 (4)	0.019 (3)	0.038 (3)	0.007 (2)	0.012 (3)	0.001 (2)
C30'_1	0.050 (4)	0.033 (3)	0.044 (4)	0.006 (3)	0.008 (3)	0.005 (3)
C31'_1	0.068 (5)	0.046 (4)	0.049 (4)	0.007 (3)	0.005 (3)	0.007 (3)
C32'_1	0.070 (5)	0.056 (4)	0.048 (4)	0.011 (4)	0.006 (4)	0.010 (3)
C33'_1	0.083 (6)	0.037 (3)	0.047 (4)	0.002 (3)	0.008 (4)	0.016 (3)
C34'_1	0.060 (4)	0.034 (3)	0.046 (4)	−0.006 (3)	0.008 (3)	−0.001 (3)
O1_2	0.033 (2)	0.0240 (19)	0.055 (2)	0.0037 (15)	−0.0001 (18)	0.0038 (16)
O2_2	0.033 (2)	0.034 (2)	0.041 (2)	−0.0010 (16)	−0.0025 (18)	0.0083 (16)
O3_2	0.030 (2)	0.040 (2)	0.042 (2)	0.0123 (18)	0.0011 (19)	0.0002 (17)
O5_2	0.027 (2)	0.0267 (19)	0.050 (2)	0.0029 (15)	0.0015 (17)	0.0033 (16)
O6_2	0.029 (2)	0.033 (2)	0.046 (2)	−0.0044 (15)	0.0075 (17)	−0.0009 (16)
O7_2	0.063 (3)	0.031 (2)	0.060 (3)	−0.013 (2)	−0.021 (2)	0.0052 (18)
O8_2	0.075 (3)	0.044 (3)	0.051 (3)	−0.004 (2)	−0.008 (2)	−0.002 (2)
O9_2	0.054 (3)	0.067 (3)	0.043 (3)	−0.022 (2)	0.009 (2)	−0.007 (2)
C1_2	0.027 (3)	0.023 (3)	0.047 (3)	−0.001 (2)	−0.004 (3)	0.005 (2)
C2_2	0.028 (3)	0.026 (3)	0.042 (3)	−0.002 (2)	−0.005 (2)	0.000 (2)
C3_2	0.026 (3)	0.023 (3)	0.043 (3)	0.000 (2)	0.000 (2)	−0.001 (2)
C4_2	0.021 (3)	0.037 (3)	0.040 (3)	0.002 (2)	−0.001 (2)	0.003 (2)
C5_2	0.026 (3)	0.026 (3)	0.044 (3)	−0.001 (2)	0.001 (2)	0.002 (2)
C6_2	0.031 (3)	0.025 (3)	0.044 (3)	−0.004 (2)	−0.001 (2)	−0.002 (2)
O2'_2	0.031 (2)	0.0261 (19)	0.042 (2)	−0.0076 (15)	0.0014 (17)	−0.0008 (15)
O3'_2	0.037 (2)	0.0207 (19)	0.050 (2)	−0.0048 (15)	−0.0076 (18)	0.0059 (15)
O1'_2	0.029 (2)	0.0259 (18)	0.039 (2)	0.0006 (15)	−0.0019 (16)	0.0019 (15)
O4'_2	0.026 (2)	0.0261 (18)	0.048 (2)	−0.0010 (15)	−0.0027 (17)	0.0037 (16)
O5'_2	0.0199 (18)	0.0220 (18)	0.050 (2)	−0.0014 (13)	0.0019 (16)	0.0038 (15)
O6'_2	0.029 (2)	0.031 (2)	0.048 (2)	0.0012 (15)	0.0010 (17)	0.0088 (17)
O7'_2	0.053 (3)	0.044 (2)	0.041 (2)	−0.0136 (19)	0.002 (2)	−0.0034 (19)
O8'_2	0.054 (3)	0.0215 (19)	0.047 (2)	−0.0091 (17)	−0.008 (2)	0.0023 (17)
O9'_2	0.029 (2)	0.046 (2)	0.056 (3)	0.0070 (18)	−0.0027 (19)	−0.001 (2)
O10'_2	0.032 (2)	0.049 (2)	0.059 (3)	−0.0003 (18)	0.006 (2)	0.0091 (19)
C1'_2	0.021 (3)	0.026 (3)	0.044 (3)	−0.001 (2)	−0.001 (2)	0.001 (2)
C2'_2	0.028 (3)	0.025 (3)	0.043 (3)	−0.005 (2)	0.001 (2)	0.004 (2)
C3'_2	0.031 (3)	0.013 (2)	0.046 (3)	−0.005 (2)	−0.008 (2)	0.007 (2)
C4'_2	0.030 (3)	0.020 (3)	0.046 (3)	0.003 (2)	−0.004 (2)	−0.002 (2)
C5'_2	0.033 (3)	0.020 (3)	0.042 (3)	0.004 (2)	−0.002 (2)	0.001 (2)
C6'_2	0.026 (3)	0.034 (3)	0.041 (3)	0.003 (2)	0.002 (2)	0.006 (2)
C7_2	0.053 (4)	0.022 (3)	0.044 (4)	−0.001 (3)	0.001 (3)	0.002 (2)
C8_2	0.054 (4)	0.027 (3)	0.039 (3)	0.008 (3)	0.006 (3)	0.000 (2)
C9_2	0.044 (4)	0.037 (3)	0.066 (4)	0.014 (3)	0.015 (3)	0.007 (3)
C10_2	0.047 (4)	0.048 (4)	0.076 (5)	0.018 (3)	0.017 (3)	0.010 (3)
C11_2	0.057 (4)	0.039 (4)	0.064 (4)	0.025 (3)	0.010 (3)	0.013 (3)
C12_2	0.067 (5)	0.029 (3)	0.048 (4)	0.010 (3)	0.010 (3)	0.003 (3)
C13_2	0.063 (4)	0.031 (3)	0.042 (3)	−0.001 (3)	0.006 (3)	−0.002 (2)
C14_2	0.049 (4)	0.029 (3)	0.047 (4)	0.006 (3)	−0.002 (3)	−0.001 (3)
C15_2	0.050 (4)	0.036 (3)	0.041 (4)	0.010 (3)	0.004 (3)	0.003 (3)
C16_2	0.043 (4)	0.047 (4)	0.045 (4)	0.000 (3)	0.000 (3)	0.007 (3)
C17_2	0.063 (4)	0.039 (3)	0.063 (5)	−0.010 (3)	0.003 (3)	0.014 (3)
C18_2	0.071 (5)	0.046 (4)	0.064 (5)	−0.004 (3)	0.006 (4)	0.019 (3)
C19_2	0.084 (6)	0.063 (5)	0.056 (5)	0.000 (4)	0.006 (4)	0.012 (4)
C20_2	0.072 (5)	0.048 (4)	0.054 (4)	0.003 (3)	0.009 (4)	−0.004 (3)
C21_2	0.036 (3)	0.025 (3)	0.041 (4)	−0.001 (2)	0.005 (3)	0.003 (2)
C22_2	0.034 (3)	0.023 (3)	0.053 (4)	0.001 (2)	0.007 (3)	0.000 (2)
C23_2	0.036 (3)	0.035 (3)	0.056 (4)	−0.007 (3)	0.004 (3)	0.001 (3)
C24_2	0.041 (4)	0.042 (3)	0.060 (4)	−0.005 (3)	0.000 (3)	−0.010 (3)
C25_2	0.037 (4)	0.033 (3)	0.077 (5)	−0.008 (3)	0.007 (3)	−0.003 (3)
C26_2	0.039 (4)	0.053 (4)	0.064 (5)	−0.008 (3)	0.016 (3)	0.000 (3)
C27_2	0.045 (4)	0.042 (3)	0.048 (4)	−0.007 (3)	0.009 (3)	0.003 (3)
C7'_2	0.038 (3)	0.032 (3)	0.037 (3)	−0.003 (2)	0.001 (3)	0.005 (3)
C8'_2	0.040 (3)	0.020 (3)	0.061 (4)	0.002 (2)	0.015 (3)	0.004 (3)
C9'_2	0.031 (3)	0.026 (3)	0.079 (5)	−0.005 (2)	0.009 (3)	−0.008 (3)
C10'_2	0.036 (4)	0.029 (3)	0.126 (7)	−0.002 (3)	0.025 (4)	−0.011 (4)
C11'_2	0.062 (5)	0.034 (4)	0.158 (9)	−0.009 (3)	0.062 (6)	−0.014 (5)
C12'_2	0.103 (7)	0.062 (5)	0.111 (7)	−0.016 (5)	0.075 (6)	−0.003 (5)
C13'_2	0.075 (5)	0.046 (4)	0.075 (5)	−0.010 (3)	0.032 (4)	−0.005 (3)
C14'_2	0.024 (3)	0.026 (3)	0.049 (4)	−0.002 (2)	0.002 (3)	−0.001 (2)
C15'_2	0.026 (3)	0.026 (3)	0.049 (4)	−0.001 (2)	0.005 (3)	−0.002 (2)
C16'_2	0.039 (3)	0.021 (3)	0.049 (4)	−0.002 (2)	0.001 (3)	0.001 (2)
C17'_2	0.050 (4)	0.033 (3)	0.050 (4)	−0.005 (3)	−0.002 (3)	−0.006 (3)
C18'_2	0.056 (4)	0.036 (3)	0.050 (4)	−0.006 (3)	0.003 (3)	0.010 (3)
C19'_2	0.047 (4)	0.021 (3)	0.069 (4)	−0.016 (2)	−0.005 (3)	0.007 (3)
C20'_2	0.032 (3)	0.030 (3)	0.051 (4)	−0.009 (2)	−0.004 (3)	0.003 (3)
C21'_2	0.026 (3)	0.038 (3)	0.050 (4)	0.002 (2)	0.001 (3)	0.006 (3)
C22'_2	0.028 (3)	0.031 (3)	0.049 (4)	−0.004 (2)	−0.005 (3)	0.010 (2)
C23'_2	0.030 (3)	0.050 (4)	0.059 (4)	−0.005 (3)	−0.005 (3)	−0.001 (3)
C24'_2	0.040 (4)	0.054 (4)	0.072 (5)	−0.008 (3)	−0.001 (3)	−0.007 (3)
C25'_2	0.045 (4)	0.061 (4)	0.064 (5)	−0.015 (3)	−0.011 (3)	0.007 (3)
C26'_2	0.028 (3)	0.052 (4)	0.065 (4)	−0.011 (3)	−0.009 (3)	0.015 (3)
C27'_2	0.027 (3)	0.047 (3)	0.054 (4)	−0.004 (3)	−0.003 (3)	0.012 (3)
C28'_2	0.031 (3)	0.028 (3)	0.047 (3)	0.001 (2)	0.013 (3)	0.003 (2)
C29'_2	0.040 (4)	0.027 (3)	0.046 (4)	0.004 (2)	0.005 (3)	0.002 (2)
C30'_2	0.046 (4)	0.039 (3)	0.046 (4)	−0.002 (3)	0.003 (3)	0.004 (3)
C31'_2	0.045 (4)	0.046 (4)	0.056 (4)	−0.002 (3)	−0.007 (3)	0.002 (3)
C32'_2	0.059 (5)	0.051 (4)	0.056 (4)	0.006 (3)	−0.004 (4)	0.018 (3)
C33'_2	0.060 (5)	0.080 (5)	0.065 (5)	−0.017 (4)	0.010 (4)	0.027 (4)
C34'_2	0.047 (4)	0.063 (4)	0.056 (4)	−0.007 (3)	0.001 (3)	0.024 (3)
O1S_3	0.102 (5)	0.078 (4)	0.113 (5)	0.007 (3)	0.021 (4)	0.037 (4)
O2S_3	0.057 (3)	0.066 (3)	0.079 (3)	0.006 (2)	−0.007 (3)	0.019 (3)
C1S_3	0.058 (6)	0.176 (11)	0.093 (7)	−0.025 (6)	−0.006 (5)	0.061 (7)
C2S_3	0.082 (6)	0.076 (6)	0.058 (5)	0.002 (5)	0.009 (4)	0.028 (4)
C3S_3	0.049 (4)	0.063 (4)	0.072 (5)	0.011 (3)	−0.010 (4)	0.002 (4)
C4S_3	0.058 (5)	0.054 (4)	0.084 (5)	0.007 (3)	−0.002 (4)	−0.005 (4)

Geometric parameters (Å, º) top

O1_1—C7_1	1.368 (7)	O5_2—C5_2	1.440 (6)
O1_1—C1_1	1.437 (6)	O6_2—C21_2	1.350 (6)
O2_1—C14_1	1.353 (6)	O6_2—C6_2	1.453 (6)
O2_1—C2_1	1.440 (6)	O7_2—C7_2	1.187 (7)
O3_1—C3_1	1.412 (6)	O8_2—C14_2	1.212 (7)
O3_1—H3O_1	0.79 (7)	O9_2—C21_2	1.204 (6)
O5_1—C1_1	1.398 (6)	C1_2—C2_2	1.522 (7)
O5_1—C5_1	1.441 (6)	C1_2—H1_2	1.0000
O6_1—C21_1	1.347 (6)	C2_2—C3_2	1.509 (7)
O6_1—C6_1	1.447 (6)	C2_2—H2_2	1.0000
O7_1—C7_1	1.193 (7)	C3_2—C4_2	1.533 (7)
O8_1—C14_1	1.207 (7)	C3_2—H3_2	1.0000
O9_1—C21_1	1.202 (7)	C4_2—O1'_2	1.433 (6)
C1_1—C2_1	1.500 (7)	C4_2—C5_2	1.525 (7)
C1_1—H1_1	1.0000	C4_2—H4_2	1.0000
C2_1—C3_1	1.524 (7)	C5_2—C6_2	1.491 (7)
C2_1—H2_1	1.0000	C5_2—H5_2	1.0000
C3_1—C4_1	1.531 (7)	C6_2—H6C_2	0.9900
C3_1—H3_1	1.0000	C6_2—H6D_2	0.9900
C4_1—O1'_1	1.436 (6)	O2'_2—C7'_2	1.349 (6)
C4_1—C5_1	1.531 (7)	O2'_2—C2'_2	1.441 (6)
C4_1—H4_1	1.0000	O3'_2—C14'_2	1.356 (6)
C5_1—C6_1	1.508 (7)	O3'_2—C3'_2	1.440 (6)
C5_1—H5_1	1.0000	O1'_2—C1'_2	1.388 (6)
C6_1—H6A_1	0.9900	O4'_2—C21'_2	1.349 (6)
C6_1—H6B_1	0.9900	O4'_2—C4'_2	1.443 (6)
O1'_1—C1'_1	1.376 (6)	O5'_2—C1'_2	1.431 (6)
O2'_1—C7'_1	1.347 (6)	O5'_2—C5'_2	1.438 (6)
O2'_1—C2'_1	1.429 (6)	O6'_2—C28'_2	1.347 (6)
O3'_1—C14'_1	1.361 (6)	O6'_2—C6'_2	1.450 (6)
O3'_1—C3'_1	1.438 (6)	O7'_2—C7'_2	1.211 (6)
O4'_1—C21'_1	1.364 (6)	O8'_2—C14'_2	1.201 (6)
O4'_1—C4'_1	1.450 (6)	O9'_2—C21'_2	1.204 (7)
O5'_1—C5'_1	1.437 (6)	O10'_2—C28'_2	1.200 (6)
O5'_1—C1'_1	1.441 (6)	C1'_2—C2'_2	1.521 (7)
O6'_1—C28'_1	1.346 (6)	C1'_2—H1'_2	1.0000
O6'_1—C6'_1	1.451 (6)	C2'_2—C3'_2	1.521 (7)
O7'_1—C7'_1	1.208 (6)	C2'_2—H2'_2	1.0000
O8'_1—C14'_1	1.194 (6)	C3'_2—C4'_2	1.507 (7)
O9'_1—C21'_1	1.199 (7)	C3'_2—H3'_2	1.0000
O10'_1—C28'_1	1.199 (7)	C4'_2—C5'_2	1.523 (7)
C1'_1—C2'_1	1.522 (7)	C4'_2—H4'_2	1.0000
C1'_1—H1'_1	1.0000	C5'_2—C6'_2	1.506 (7)
C2'_1—C3'_1	1.508 (7)	C5'_2—H5'_2	1.0000
C2'_1—H2'_1	1.0000	C6'_2—H6'C_2	0.9900
C3'_1—C4'_1	1.503 (7)	C6'_2—H6'D_2	0.9900
C3'_1—H3'_1	1.0000	C7_2—C8_2	1.499 (8)
C4'_1—C5'_1	1.523 (7)	C8_2—C9_2	1.376 (8)
C4'_1—H4'_1	1.0000	C8_2—C13_2	1.389 (8)
C5'_1—C6'_1	1.493 (7)	C9_2—C10_2	1.393 (9)
C5'_1—H5'_1	1.0000	C9_2—H9_2	0.9500
C6'_1—H6'A_1	0.9900	C10_2—C11_2	1.372 (9)
C6'_1—H6'B_1	0.9900	C10_2—H10_2	0.9500
C7_1—C8_1	1.478 (8)	C11_2—C12_2	1.370 (9)
C8_1—C13_1	1.390 (8)	C11_2—H11_2	0.9500
C8_1—C9_1	1.394 (8)	C12_2—C13_2	1.396 (8)
C9_1—C10_1	1.376 (9)	C12_2—H12_2	0.9500
C9_1—H9_1	0.9500	C13_2—H13_2	0.9500
C10_1—C11_1	1.376 (10)	C14_2—C15_2	1.502 (8)
C10_1—H10_1	0.9500	C15_2—C16_2	1.363 (8)
C11_1—C12_1	1.403 (9)	C15_2—C20_2	1.387 (8)
C11_1—H11_1	0.9500	C16_2—C17_2	1.381 (8)
C12_1—C13_1	1.379 (8)	C16_2—H16_2	0.9500
C12_1—H12_1	0.9500	C17_2—C18_2	1.378 (9)
C13_1—H13_1	0.9500	C17_2—H17_2	0.9500
C14_1—C15_1	1.490 (8)	C18_2—C19_2	1.364 (10)
C15_1—C16_1	1.388 (8)	C18_2—H18_2	0.9500
C15_1—C20_1	1.389 (8)	C19_2—C20_2	1.395 (9)
C16_1—C17_1	1.371 (8)	C19_2—H19_2	0.9500
C16_1—H16_1	0.9500	C20_2—H20_2	0.9500
C17_1—C18_1	1.380 (9)	C21_2—C22_2	1.491 (8)
C17_1—H17_1	0.9500	C22_2—C23_2	1.376 (8)
C18_1—C19_1	1.377 (10)	C22_2—C27_2	1.392 (8)
C18_1—H18_1	0.9500	C23_2—C24_2	1.392 (8)
C19_1—C20_1	1.384 (9)	C23_2—H23_2	0.9500
C19_1—H19_1	0.9500	C24_2—C25_2	1.382 (9)
C20_1—H20_1	0.9500	C24_2—H24_2	0.9500
C21_1—C22_1	1.502 (8)	C25_2—C26_2	1.360 (9)
C22_1—C23_1	1.357 (8)	C25_2—H25_2	0.9500
C22_1—C27_1	1.380 (8)	C26_2—C27_2	1.385 (8)
C23_1—C24_1	1.409 (9)	C26_2—H26_2	0.9500
C23_1—H23_1	0.9500	C27_2—H27_2	0.9500
C24_1—C25_1	1.392 (11)	C7'_2—C8'_2	1.495 (7)
C24_1—H24_1	0.9500	C8'_2—C9'_2	1.371 (8)
C25_1—C26_1	1.354 (10)	C8'_2—C13'_2	1.386 (9)
C25_1—H25_1	0.9500	C9'_2—C10'_2	1.386 (8)
C26_1—C27_1	1.392 (9)	C9'_2—H9'_2	0.9500
C26_1—H26_1	0.9500	C10'_2—C11'_2	1.370 (11)
C27_1—H27_1	0.9500	C10'_2—H10'_2	0.9500
C7'_1—C8'_1	1.487 (7)	C11'_2—C12'_2	1.369 (12)
C8'_1—C9'_1	1.381 (8)	C11'_2—H11'_2	0.9500
C8'_1—C13'_1	1.384 (8)	C12'_2—C13'_2	1.375 (10)
C9'_1—C10'_1	1.392 (8)	C12'_2—H12'_2	0.9500
C9'_1—H9'_1	0.9500	C13'_2—H13'_2	0.9500
C10'_1—C11'_1	1.361 (9)	C14'_2—C15'_2	1.480 (8)
C10'_1—H10'_1	0.9500	C15'_2—C16'_2	1.385 (8)
C11'_1—C12'_1	1.378 (9)	C15'_2—C20'_2	1.398 (7)
C11'_1—H11'_1	0.9500	C16'_2—C17'_2	1.385 (8)
C12'_1—C13'_1	1.376 (9)	C16'_2—H16'_2	0.9500
C12'_1—H12'_1	0.9500	C17'_2—C18'_2	1.391 (8)
C13'_1—H13'_1	0.9500	C17'_2—H17'_2	0.9500
C14'_1—C15'_1	1.486 (8)	C18'_2—C19'_2	1.385 (8)
C15'_1—C16'_1	1.389 (8)	C18'_2—H18'_2	0.9500
C15'_1—C20'_1	1.393 (8)	C19'_2—C20'_2	1.369 (8)
C16'_1—C17'_1	1.380 (8)	C19'_2—H19'_2	0.9500
C16'_1—H16'_1	0.9500	C20'_2—H20'_2	0.9500
C17'_1—C18'_1	1.388 (9)	C21'_2—C22'_2	1.493 (8)
C17'_1—H17'_1	0.9500	C22'_2—C23'_2	1.376 (8)
C18'_1—C19'_1	1.381 (9)	C22'_2—C27'_2	1.402 (8)
C18'_1—H18'_1	0.9500	C23'_2—C24'_2	1.383 (9)
C19'_1—C20'_1	1.368 (8)	C23'_2—H23'_2	0.9500
C19'_1—H19'_1	0.9500	C24'_2—C25'_2	1.382 (9)
C20'_1—H20'_1	0.9500	C24'_2—H24'_2	0.9500
C21'_1—C22'_1	1.470 (8)	C25'_2—C26'_2	1.381 (9)
C22'_1—C27'_1	1.391 (7)	C25'_2—H25'_2	0.9500
C22'_1—C23'_1	1.394 (7)	C26'_2—C27'_2	1.395 (8)
C23'_1—C24'_1	1.397 (8)	C26'_2—H26'_2	0.9500
C23'_1—H23'_1	0.9500	C27'_2—H27'_2	0.9500
C24'_1—C25'_1	1.400 (8)	C28'_2—C29'_2	1.504 (8)
C24'_1—H24'_1	0.9500	C29'_2—C34'_2	1.373 (8)
C25'_1—C26'_1	1.367 (8)	C29'_2—C30'_2	1.377 (8)
C25'_1—H25'_1	0.9500	C30'_2—C31'_2	1.383 (8)
C26'_1—C27'_1	1.371 (8)	C30'_2—H30'_2	0.9500
C26'_1—H26'_1	0.9500	C31'_2—C32'_2	1.371 (9)
C27'_1—H27'_1	0.9500	C31'_2—H31'_2	0.9500
C28'_1—C29'_1	1.509 (8)	C32'_2—C33'_2	1.381 (9)
C29'_1—C30'_1	1.376 (8)	C32'_2—H32'_2	0.9500
C29'_1—C34'_1	1.382 (8)	C33'_2—C34'_2	1.366 (9)
C30'_1—C31'_1	1.375 (8)	C33'_2—H33'_2	0.9500
C30'_1—H30'_1	0.9500	C34'_2—H34'_2	0.9500
C31'_1—C32'_1	1.376 (9)	O1S_3—C2S_3	1.216 (9)
C31'_1—H31'_1	0.9500	O2S_3—C2S_3	1.324 (9)
C32'_1—C33'_1	1.357 (9)	O2S_3—C3S_3	1.459 (8)
C32'_1—H32'_1	0.9500	C1S_3—C2S_3	1.450 (11)
C33'_1—C34'_1	1.388 (9)	C1S_3—H1SA_3	0.9800
C33'_1—H33'_1	0.9500	C1S_3—H1SB_3	0.9800
C34'_1—H34'_1	0.9500	C1S_3—H1SC_3	0.9800
O1_2—C7_2	1.374 (6)	C3S_3—C4S_3	1.528 (10)
O1_2—C1_2	1.413 (6)	C3S_3—H3SA_3	0.9900
O2_2—C14_2	1.336 (7)	C3S_3—H3SB_3	0.9900
O2_2—C2_2	1.440 (6)	C4S_3—H4SA_3	0.9800
O3_2—C3_2	1.434 (6)	C4S_3—H4SB_3	0.9800
O3_2—H3O_2	0.73 (7)	C4S_3—H4SC_3	0.9800
O5_2—C1_2	1.415 (6)

C7_1—O1_1—C1_1	116.2 (4)	O2_2—C2_2—C3_2	111.3 (4)
C14_1—O2_1—C2_1	117.6 (4)	O2_2—C2_2—C1_2	104.6 (4)
C3_1—O3_1—H3O_1	107 (5)	C3_2—C2_2—C1_2	108.7 (4)
C1_1—O5_1—C5_1	109.1 (4)	O2_2—C2_2—H2_2	110.7
C21_1—O6_1—C6_1	114.0 (4)	C3_2—C2_2—H2_2	110.7
O5_1—C1_1—O1_1	107.1 (4)	C1_2—C2_2—H2_2	110.7
O5_1—C1_1—C2_1	109.6 (4)	O3_2—C3_2—C2_2	107.6 (4)
O1_1—C1_1—C2_1	108.9 (4)	O3_2—C3_2—C4_2	112.1 (4)
O5_1—C1_1—H1_1	110.4	C2_2—C3_2—C4_2	110.2 (4)
O1_1—C1_1—H1_1	110.4	O3_2—C3_2—H3_2	109.0
C2_1—C1_1—H1_1	110.4	C2_2—C3_2—H3_2	109.0
O2_1—C2_1—C1_1	107.4 (4)	C4_2—C3_2—H3_2	109.0
O2_1—C2_1—C3_1	109.5 (4)	O1'_2—C4_2—C5_2	103.8 (4)
C1_1—C2_1—C3_1	109.1 (4)	O1'_2—C4_2—C3_2	113.2 (4)
O2_1—C2_1—H2_1	110.3	C5_2—C4_2—C3_2	110.0 (4)
C1_1—C2_1—H2_1	110.3	O1'_2—C4_2—H4_2	109.9
C3_1—C2_1—H2_1	110.3	C5_2—C4_2—H4_2	109.9
O3_1—C3_1—C2_1	107.9 (4)	C3_2—C4_2—H4_2	109.9
O3_1—C3_1—C4_1	112.4 (4)	O5_2—C5_2—C6_2	109.4 (4)
C2_1—C3_1—C4_1	109.1 (4)	O5_2—C5_2—C4_2	109.0 (4)
O3_1—C3_1—H3_1	109.1	C6_2—C5_2—C4_2	116.7 (4)
C2_1—C3_1—H3_1	109.1	O5_2—C5_2—H5_2	107.1
C4_1—C3_1—H3_1	109.1	C6_2—C5_2—H5_2	107.1
O1'_1—C4_1—C3_1	113.0 (4)	C4_2—C5_2—H5_2	107.1
O1'_1—C4_1—C5_1	103.8 (4)	O6_2—C6_2—C5_2	109.7 (4)
C3_1—C4_1—C5_1	110.9 (4)	O6_2—C6_2—H6C_2	109.7
O1'_1—C4_1—H4_1	109.7	C5_2—C6_2—H6C_2	109.7
C3_1—C4_1—H4_1	109.7	O6_2—C6_2—H6D_2	109.7
C5_1—C4_1—H4_1	109.7	C5_2—C6_2—H6D_2	109.7
O5_1—C5_1—C6_1	108.3 (4)	H6C_2—C6_2—H6D_2	108.2
O5_1—C5_1—C4_1	110.2 (4)	C7'_2—O2'_2—C2'_2	118.2 (4)
C6_1—C5_1—C4_1	113.9 (4)	C14'_2—O3'_2—C3'_2	116.0 (4)
O5_1—C5_1—H5_1	108.1	C1'_2—O1'_2—C4_2	118.0 (4)
C6_1—C5_1—H5_1	108.1	C21'_2—O4'_2—C4'_2	116.4 (4)
C4_1—C5_1—H5_1	108.1	C1'_2—O5'_2—C5'_2	112.7 (4)
O6_1—C6_1—C5_1	109.2 (4)	C28'_2—O6'_2—C6'_2	113.9 (4)
O6_1—C6_1—H6A_1	109.8	O1'_2—C1'_2—O5'_2	107.3 (4)
C5_1—C6_1—H6A_1	109.8	O1'_2—C1'_2—C2'_2	107.6 (4)
O6_1—C6_1—H6B_1	109.8	O5'_2—C1'_2—C2'_2	109.2 (4)
C5_1—C6_1—H6B_1	109.8	O1'_2—C1'_2—H1'_2	110.9
H6A_1—C6_1—H6B_1	108.3	O5'_2—C1'_2—H1'_2	110.9
C1'_1—O1'_1—C4_1	117.0 (4)	C2'_2—C1'_2—H1'_2	110.9
C7'_1—O2'_1—C2'_1	119.2 (4)	O2'_2—C2'_2—C3'_2	105.7 (4)
C14'_1—O3'_1—C3'_1	116.8 (4)	O2'_2—C2'_2—C1'_2	108.0 (4)
C21'_1—O4'_1—C4'_1	116.9 (4)	C3'_2—C2'_2—C1'_2	110.4 (4)
C5'_1—O5'_1—C1'_1	112.2 (3)	O2'_2—C2'_2—H2'_2	110.9
C28'_1—O6'_1—C6'_1	114.9 (4)	C3'_2—C2'_2—H2'_2	110.9
O1'_1—C1'_1—O5'_1	107.4 (4)	C1'_2—C2'_2—H2'_2	110.9
O1'_1—C1'_1—C2'_1	108.4 (4)	O3'_2—C3'_2—C4'_2	110.6 (4)
O5'_1—C1'_1—C2'_1	109.0 (4)	O3'_2—C3'_2—C2'_2	108.4 (4)
O1'_1—C1'_1—H1'_1	110.6	C4'_2—C3'_2—C2'_2	111.3 (4)
O5'_1—C1'_1—H1'_1	110.6	O3'_2—C3'_2—H3'_2	108.8
C2'_1—C1'_1—H1'_1	110.6	C4'_2—C3'_2—H3'_2	108.8
O2'_1—C2'_1—C3'_1	107.5 (4)	C2'_2—C3'_2—H3'_2	108.8
O2'_1—C2'_1—C1'_1	107.9 (4)	O4'_2—C4'_2—C3'_2	109.0 (4)
C3'_1—C2'_1—C1'_1	109.9 (4)	O4'_2—C4'_2—C5'_2	110.1 (4)
O2'_1—C2'_1—H2'_1	110.5	C3'_2—C4'_2—C5'_2	107.8 (4)
C3'_1—C2'_1—H2'_1	110.5	O4'_2—C4'_2—H4'_2	109.9
C1'_1—C2'_1—H2'_1	110.5	C3'_2—C4'_2—H4'_2	109.9
O3'_1—C3'_1—C4'_1	109.9 (4)	C5'_2—C4'_2—H4'_2	109.9
O3'_1—C3'_1—C2'_1	109.7 (4)	O5'_2—C5'_2—C6'_2	106.1 (4)
C4'_1—C3'_1—C2'_1	113.4 (4)	O5'_2—C5'_2—C4'_2	110.1 (4)
O3'_1—C3'_1—H3'_1	107.9	C6'_2—C5'_2—C4'_2	113.6 (4)
C4'_1—C3'_1—H3'_1	107.9	O5'_2—C5'_2—H5'_2	109.0
C2'_1—C3'_1—H3'_1	107.9	C6'_2—C5'_2—H5'_2	109.0
O4'_1—C4'_1—C3'_1	108.8 (4)	C4'_2—C5'_2—H5'_2	109.0
O4'_1—C4'_1—C5'_1	109.8 (4)	O6'_2—C6'_2—C5'_2	105.7 (4)
C3'_1—C4'_1—C5'_1	108.2 (4)	O6'_2—C6'_2—H6'C_2	110.6
O4'_1—C4'_1—H4'_1	110.0	C5'_2—C6'_2—H6'C_2	110.6
C3'_1—C4'_1—H4'_1	110.0	O6'_2—C6'_2—H6'D_2	110.6
C5'_1—C4'_1—H4'_1	110.0	C5'_2—C6'_2—H6'D_2	110.6
O5'_1—C5'_1—C6'_1	106.9 (4)	H6'C_2—C6'_2—H6'D_2	108.7
O5'_1—C5'_1—C4'_1	110.0 (4)	O7_2—C7_2—O1_2	123.2 (5)
C6'_1—C5'_1—C4'_1	114.3 (4)	O7_2—C7_2—C8_2	124.5 (5)
O5'_1—C5'_1—H5'_1	108.5	O1_2—C7_2—C8_2	112.3 (5)
C6'_1—C5'_1—H5'_1	108.5	C9_2—C8_2—C13_2	120.4 (6)
C4'_1—C5'_1—H5'_1	108.5	C9_2—C8_2—C7_2	122.6 (5)
O6'_1—C6'_1—C5'_1	105.3 (4)	C13_2—C8_2—C7_2	116.9 (5)
O6'_1—C6'_1—H6'A_1	110.7	C8_2—C9_2—C10_2	119.5 (6)
C5'_1—C6'_1—H6'A_1	110.7	C8_2—C9_2—H9_2	120.3
O6'_1—C6'_1—H6'B_1	110.7	C10_2—C9_2—H9_2	120.3
C5'_1—C6'_1—H6'B_1	110.7	C11_2—C10_2—C9_2	120.1 (6)
H6'A_1—C6'_1—H6'B_1	108.8	C11_2—C10_2—H10_2	119.9
O7_1—C7_1—O1_1	122.7 (5)	C9_2—C10_2—H10_2	119.9
O7_1—C7_1—C8_1	125.4 (5)	C12_2—C11_2—C10_2	120.7 (6)
O1_1—C7_1—C8_1	111.8 (5)	C12_2—C11_2—H11_2	119.6
C13_1—C8_1—C9_1	119.7 (5)	C10_2—C11_2—H11_2	119.6
C13_1—C8_1—C7_1	117.3 (5)	C11_2—C12_2—C13_2	119.8 (6)
C9_1—C8_1—C7_1	122.9 (5)	C11_2—C12_2—H12_2	120.1
C10_1—C9_1—C8_1	119.9 (6)	C13_2—C12_2—H12_2	120.1
C10_1—C9_1—H9_1	120.1	C8_2—C13_2—C12_2	119.4 (6)
C8_1—C9_1—H9_1	120.1	C8_2—C13_2—H13_2	120.3
C11_1—C10_1—C9_1	120.7 (7)	C12_2—C13_2—H13_2	120.3
C11_1—C10_1—H10_1	119.6	O8_2—C14_2—O2_2	123.7 (5)
C9_1—C10_1—H10_1	119.6	O8_2—C14_2—C15_2	124.2 (6)
C10_1—C11_1—C12_1	119.8 (6)	O2_2—C14_2—C15_2	112.1 (5)
C10_1—C11_1—H11_1	120.1	C16_2—C15_2—C20_2	120.0 (6)
C12_1—C11_1—H11_1	120.1	C16_2—C15_2—C14_2	121.3 (5)
C13_1—C12_1—C11_1	119.6 (6)	C20_2—C15_2—C14_2	118.6 (5)
C13_1—C12_1—H12_1	120.2	C15_2—C16_2—C17_2	120.3 (6)
C11_1—C12_1—H12_1	120.2	C15_2—C16_2—H16_2	119.9
C12_1—C13_1—C8_1	120.3 (6)	C17_2—C16_2—H16_2	119.9
C12_1—C13_1—H13_1	119.8	C18_2—C17_2—C16_2	120.2 (6)
C8_1—C13_1—H13_1	119.8	C18_2—C17_2—H17_2	119.9
O8_1—C14_1—O2_1	123.5 (5)	C16_2—C17_2—H17_2	119.9
O8_1—C14_1—C15_1	124.3 (5)	C19_2—C18_2—C17_2	120.1 (6)
O2_1—C14_1—C15_1	112.1 (5)	C19_2—C18_2—H18_2	119.9
C16_1—C15_1—C20_1	119.5 (5)	C17_2—C18_2—H18_2	119.9
C16_1—C15_1—C14_1	121.8 (5)	C18_2—C19_2—C20_2	119.9 (7)
C20_1—C15_1—C14_1	118.6 (5)	C18_2—C19_2—H19_2	120.1
C17_1—C16_1—C15_1	119.5 (6)	C20_2—C19_2—H19_2	120.1
C17_1—C16_1—H16_1	120.3	C15_2—C20_2—C19_2	119.6 (6)
C15_1—C16_1—H16_1	120.3	C15_2—C20_2—H20_2	120.2
C16_1—C17_1—C18_1	121.0 (7)	C19_2—C20_2—H20_2	120.2
C16_1—C17_1—H17_1	119.5	O9_2—C21_2—O6_2	122.9 (5)
C18_1—C17_1—H17_1	119.5	O9_2—C21_2—C22_2	124.2 (5)
C19_1—C18_1—C17_1	120.1 (7)	O6_2—C21_2—C22_2	112.9 (5)
C19_1—C18_1—H18_1	119.9	C23_2—C22_2—C27_2	119.1 (5)
C17_1—C18_1—H18_1	119.9	C23_2—C22_2—C21_2	123.8 (5)
C18_1—C19_1—C20_1	119.4 (6)	C27_2—C22_2—C21_2	117.1 (5)
C18_1—C19_1—H19_1	120.3	C22_2—C23_2—C24_2	120.7 (6)
C20_1—C19_1—H19_1	120.3	C22_2—C23_2—H23_2	119.7
C19_1—C20_1—C15_1	120.6 (6)	C24_2—C23_2—H23_2	119.7
C19_1—C20_1—H20_1	119.7	C25_2—C24_2—C23_2	118.7 (6)
C15_1—C20_1—H20_1	119.7	C25_2—C24_2—H24_2	120.6
O9_1—C21_1—O6_1	122.0 (5)	C23_2—C24_2—H24_2	120.6
O9_1—C21_1—C22_1	124.7 (5)	C26_2—C25_2—C24_2	121.5 (6)
O6_1—C21_1—C22_1	113.3 (5)	C26_2—C25_2—H25_2	119.2
C23_1—C22_1—C27_1	121.6 (6)	C24_2—C25_2—H25_2	119.2
C23_1—C22_1—C21_1	122.2 (5)	C25_2—C26_2—C27_2	119.5 (6)
C27_1—C22_1—C21_1	116.2 (6)	C25_2—C26_2—H26_2	120.2
C22_1—C23_1—C24_1	119.4 (6)	C27_2—C26_2—H26_2	120.2
C22_1—C23_1—H23_1	120.3	C26_2—C27_2—C22_2	120.4 (6)
C24_1—C23_1—H23_1	120.3	C26_2—C27_2—H27_2	119.8
C25_1—C24_1—C23_1	118.6 (7)	C22_2—C27_2—H27_2	119.8
C25_1—C24_1—H24_1	120.7	O7'_2—C7'_2—O2'_2	124.1 (5)
C23_1—C24_1—H24_1	120.7	O7'_2—C7'_2—C8'_2	125.3 (5)
C26_1—C25_1—C24_1	121.3 (7)	O2'_2—C7'_2—C8'_2	110.5 (5)
C26_1—C25_1—H25_1	119.4	C9'_2—C8'_2—C13'_2	119.9 (6)
C24_1—C25_1—H25_1	119.4	C9'_2—C8'_2—C7'_2	122.3 (5)
C25_1—C26_1—C27_1	120.0 (7)	C13'_2—C8'_2—C7'_2	117.8 (6)
C25_1—C26_1—H26_1	120.0	C8'_2—C9'_2—C10'_2	120.8 (6)
C27_1—C26_1—H26_1	120.0	C8'_2—C9'_2—H9'_2	119.6
C22_1—C27_1—C26_1	119.1 (7)	C10'_2—C9'_2—H9'_2	119.6
C22_1—C27_1—H27_1	120.5	C11'_2—C10'_2—C9'_2	118.6 (7)
C26_1—C27_1—H27_1	120.5	C11'_2—C10'_2—H10'_2	120.7
O7'_1—C7'_1—O2'_1	123.4 (5)	C9'_2—C10'_2—H10'_2	120.7
O7'_1—C7'_1—C8'_1	124.4 (5)	C12'_2—C11'_2—C10'_2	121.1 (7)
O2'_1—C7'_1—C8'_1	112.2 (4)	C12'_2—C11'_2—H11'_2	119.4
C9'_1—C8'_1—C13'_1	119.1 (5)	C10'_2—C11'_2—H11'_2	119.4
C9'_1—C8'_1—C7'_1	121.5 (5)	C11'_2—C12'_2—C13'_2	120.4 (7)
C13'_1—C8'_1—C7'_1	119.4 (5)	C11'_2—C12'_2—H12'_2	119.8
C8'_1—C9'_1—C10'_1	119.8 (6)	C13'_2—C12'_2—H12'_2	119.8
C8'_1—C9'_1—H9'_1	120.1	C12'_2—C13'_2—C8'_2	119.1 (7)
C10'_1—C9'_1—H9'_1	120.1	C12'_2—C13'_2—H13'_2	120.4
C11'_1—C10'_1—C9'_1	120.7 (6)	C8'_2—C13'_2—H13'_2	120.4
C11'_1—C10'_1—H10'_1	119.7	O8'_2—C14'_2—O3'_2	123.0 (5)
C9'_1—C10'_1—H10'_1	119.7	O8'_2—C14'_2—C15'_2	124.9 (5)
C10'_1—C11'_1—C12'_1	119.7 (6)	O3'_2—C14'_2—C15'_2	112.1 (5)
C10'_1—C11'_1—H11'_1	120.2	C16'_2—C15'_2—C20'_2	120.1 (5)
C12'_1—C11'_1—H11'_1	120.2	C16'_2—C15'_2—C14'_2	122.5 (5)
C13'_1—C12'_1—C11'_1	120.3 (6)	C20'_2—C15'_2—C14'_2	117.4 (5)
C13'_1—C12'_1—H12'_1	119.8	C17'_2—C16'_2—C15'_2	119.8 (5)
C11'_1—C12'_1—H12'_1	119.8	C17'_2—C16'_2—H16'_2	120.1
C12'_1—C13'_1—C8'_1	120.4 (6)	C15'_2—C16'_2—H16'_2	120.1
C12'_1—C13'_1—H13'_1	119.8	C16'_2—C17'_2—C18'_2	119.8 (6)
C8'_1—C13'_1—H13'_1	119.8	C16'_2—C17'_2—H17'_2	120.1
O8'_1—C14'_1—O3'_1	123.0 (5)	C18'_2—C17'_2—H17'_2	120.1
O8'_1—C14'_1—C15'_1	125.4 (5)	C19'_2—C18'_2—C17'_2	120.1 (6)
O3'_1—C14'_1—C15'_1	111.6 (5)	C19'_2—C18'_2—H18'_2	120.0
C16'_1—C15'_1—C20'_1	119.4 (5)	C17'_2—C18'_2—H18'_2	120.0
C16'_1—C15'_1—C14'_1	122.9 (5)	C20'_2—C19'_2—C18'_2	120.4 (5)
C20'_1—C15'_1—C14'_1	117.7 (5)	C20'_2—C19'_2—H19'_2	119.8
C17'_1—C16'_1—C15'_1	120.4 (5)	C18'_2—C19'_2—H19'_2	119.8
C17'_1—C16'_1—H16'_1	119.8	C19'_2—C20'_2—C15'_2	119.8 (5)
C15'_1—C16'_1—H16'_1	119.8	C19'_2—C20'_2—H20'_2	120.1
C16'_1—C17'_1—C18'_1	119.7 (6)	C15'_2—C20'_2—H20'_2	120.1
C16'_1—C17'_1—H17'_1	120.1	O9'_2—C21'_2—O4'_2	122.9 (5)
C18'_1—C17'_1—H17'_1	120.1	O9'_2—C21'_2—C22'_2	124.5 (5)
C19'_1—C18'_1—C17'_1	119.7 (6)	O4'_2—C21'_2—C22'_2	112.5 (5)
C19'_1—C18'_1—H18'_1	120.2	C23'_2—C22'_2—C27'_2	121.0 (5)
C17'_1—C18'_1—H18'_1	120.2	C23'_2—C22'_2—C21'_2	122.9 (5)
C20'_1—C19'_1—C18'_1	120.9 (6)	C27'_2—C22'_2—C21'_2	116.1 (5)
C20'_1—C19'_1—H19'_1	119.5	C22'_2—C23'_2—C24'_2	119.7 (6)
C18'_1—C19'_1—H19'_1	119.5	C22'_2—C23'_2—H23'_2	120.1
C19'_1—C20'_1—C15'_1	119.9 (6)	C24'_2—C23'_2—H23'_2	120.1
C19'_1—C20'_1—H20'_1	120.1	C25'_2—C24'_2—C23'_2	120.3 (7)
C15'_1—C20'_1—H20'_1	120.1	C25'_2—C24'_2—H24'_2	119.9
O9'_1—C21'_1—O4'_1	122.2 (5)	C23'_2—C24'_2—H24'_2	119.9
O9'_1—C21'_1—C22'_1	124.7 (5)	C26'_2—C25'_2—C24'_2	120.1 (6)
O4'_1—C21'_1—C22'_1	113.1 (4)	C26'_2—C25'_2—H25'_2	120.0
C27'_1—C22'_1—C23'_1	119.9 (5)	C24'_2—C25'_2—H25'_2	120.0
C27'_1—C22'_1—C21'_1	117.8 (5)	C25'_2—C26'_2—C27'_2	120.6 (6)
C23'_1—C22'_1—C21'_1	122.3 (5)	C25'_2—C26'_2—H26'_2	119.7
C22'_1—C23'_1—C24'_1	119.4 (5)	C27'_2—C26'_2—H26'_2	119.7
C22'_1—C23'_1—H23'_1	120.3	C26'_2—C27'_2—C22'_2	118.2 (6)
C24'_1—C23'_1—H23'_1	120.3	C26'_2—C27'_2—H27'_2	120.9
C23'_1—C24'_1—C25'_1	119.5 (6)	C22'_2—C27'_2—H27'_2	120.9
C23'_1—C24'_1—H24'_1	120.3	O10'_2—C28'_2—O6'_2	123.0 (5)
C25'_1—C24'_1—H24'_1	120.3	O10'_2—C28'_2—C29'_2	124.9 (5)
C26'_1—C25'_1—C24'_1	120.3 (5)	O6'_2—C28'_2—C29'_2	112.0 (5)
C26'_1—C25'_1—H25'_1	119.8	C34'_2—C29'_2—C30'_2	119.8 (6)
C24'_1—C25'_1—H25'_1	119.8	C34'_2—C29'_2—C28'_2	117.6 (5)
C25'_1—C26'_1—C27'_1	120.6 (5)	C30'_2—C29'_2—C28'_2	122.5 (5)
C25'_1—C26'_1—H26'_1	119.7	C29'_2—C30'_2—C31'_2	119.4 (6)
C27'_1—C26'_1—H26'_1	119.7	C29'_2—C30'_2—H30'_2	120.3
C26'_1—C27'_1—C22'_1	120.3 (5)	C31'_2—C30'_2—H30'_2	120.3
C26'_1—C27'_1—H27'_1	119.9	C32'_2—C31'_2—C30'_2	120.2 (6)
C22'_1—C27'_1—H27'_1	119.9	C32'_2—C31'_2—H31'_2	119.9
O10'_1—C28'_1—O6'_1	122.7 (5)	C30'_2—C31'_2—H31'_2	119.9
O10'_1—C28'_1—C29'_1	124.7 (5)	C31'_2—C32'_2—C33'_2	120.2 (6)
O6'_1—C28'_1—C29'_1	112.7 (5)	C31'_2—C32'_2—H32'_2	119.9
C30'_1—C29'_1—C34'_1	119.8 (6)	C33'_2—C32'_2—H32'_2	119.9
C30'_1—C29'_1—C28'_1	123.3 (5)	C34'_2—C33'_2—C32'_2	119.3 (6)
C34'_1—C29'_1—C28'_1	116.9 (6)	C34'_2—C33'_2—H33'_2	120.4
C31'_1—C30'_1—C29'_1	119.8 (6)	C32'_2—C33'_2—H33'_2	120.4
C31'_1—C30'_1—H30'_1	120.1	C33'_2—C34'_2—C29'_2	121.0 (6)
C29'_1—C30'_1—H30'_1	120.1	C33'_2—C34'_2—H34'_2	119.5
C30'_1—C31'_1—C32'_1	120.2 (7)	C29'_2—C34'_2—H34'_2	119.5
C30'_1—C31'_1—H31'_1	119.9	C2S_3—O2S_3—C3S_3	117.9 (6)
C32'_1—C31'_1—H31'_1	119.9	C2S_3—C1S_3—H1SA_3	109.5
C33'_1—C32'_1—C31'_1	120.3 (6)	C2S_3—C1S_3—H1SB_3	109.5
C33'_1—C32'_1—H32'_1	119.8	H1SA_3—C1S_3—H1SB_3	109.5
C31'_1—C32'_1—H32'_1	119.8	C2S_3—C1S_3—H1SC_3	109.5
C32'_1—C33'_1—C34'_1	120.0 (6)	H1SA_3—C1S_3—H1SC_3	109.5
C32'_1—C33'_1—H33'_1	120.0	H1SB_3—C1S_3—H1SC_3	109.5
C34'_1—C33'_1—H33'_1	120.0	O1S_3—C2S_3—O2S_3	120.9 (8)
C29'_1—C34'_1—C33'_1	119.7 (6)	O1S_3—C2S_3—C1S_3	125.6 (8)
C29'_1—C34'_1—H34'_1	120.1	O2S_3—C2S_3—C1S_3	113.5 (7)
C33'_1—C34'_1—H34'_1	120.1	O2S_3—C3S_3—C4S_3	106.1 (5)
C7_2—O1_2—C1_2	115.5 (4)	O2S_3—C3S_3—H3SA_3	110.5
C14_2—O2_2—C2_2	119.7 (4)	C4S_3—C3S_3—H3SA_3	110.5
C3_2—O3_2—H3O_2	102 (5)	O2S_3—C3S_3—H3SB_3	110.5
C1_2—O5_2—C5_2	109.2 (4)	C4S_3—C3S_3—H3SB_3	110.5
C21_2—O6_2—C6_2	113.9 (4)	H3SA_3—C3S_3—H3SB_3	108.7
O1_2—C1_2—O5_2	106.0 (4)	C3S_3—C4S_3—H4SA_3	109.5
O1_2—C1_2—C2_2	110.1 (4)	C3S_3—C4S_3—H4SB_3	109.5
O5_2—C1_2—C2_2	109.2 (4)	H4SA_3—C4S_3—H4SB_3	109.5
O1_2—C1_2—H1_2	110.5	C3S_3—C4S_3—H4SC_3	109.5
O5_2—C1_2—H1_2	110.5	H4SA_3—C4S_3—H4SC_3	109.5
C2_2—C1_2—H1_2	110.5	H4SB_3—C4S_3—H4SC_3	109.5

C5_1—O5_1—C1_1—O1_1	173.3 (4)	C5_2—O5_2—C1_2—O1_2	172.9 (4)
C5_1—O5_1—C1_1—C2_1	−68.8 (5)	C5_2—O5_2—C1_2—C2_2	−68.5 (5)
C7_1—O1_1—C1_1—O5_1	−139.3 (4)	C14_2—O2_2—C2_2—C3_2	−114.4 (5)
C7_1—O1_1—C1_1—C2_1	102.2 (5)	C14_2—O2_2—C2_2—C1_2	128.4 (5)
C14_1—O2_1—C2_1—C1_1	111.1 (5)	O1_2—C1_2—C2_2—O2_2	−63.2 (5)
C14_1—O2_1—C2_1—C3_1	−130.5 (5)	O5_2—C1_2—C2_2—O2_2	−179.2 (4)
O5_1—C1_1—C2_1—O2_1	−177.3 (4)	O1_2—C1_2—C2_2—C3_2	177.8 (4)
O1_1—C1_1—C2_1—O2_1	−60.5 (5)	O5_2—C1_2—C2_2—C3_2	61.8 (5)
O5_1—C1_1—C2_1—C3_1	64.1 (5)	O2_2—C2_2—C3_2—O3_2	69.5 (5)
O1_1—C1_1—C2_1—C3_1	−179.1 (4)	C1_2—C2_2—C3_2—O3_2	−175.9 (4)
O2_1—C2_1—C3_1—O3_1	66.7 (5)	O2_2—C2_2—C3_2—C4_2	−168.1 (4)
C1_1—C2_1—C3_1—O3_1	−176.0 (4)	C1_2—C2_2—C3_2—C4_2	−53.4 (5)
O2_1—C2_1—C3_1—C4_1	−170.9 (4)	O3_2—C3_2—C4_2—O1'_2	−72.6 (6)
C1_1—C2_1—C3_1—C4_1	−53.6 (5)	C2_2—C3_2—C4_2—O1'_2	167.6 (4)
O3_1—C3_1—C4_1—O1'_1	−74.7 (5)	O3_2—C3_2—C4_2—C5_2	171.8 (4)
C2_1—C3_1—C4_1—O1'_1	165.6 (4)	C2_2—C3_2—C4_2—C5_2	52.0 (6)
O3_1—C3_1—C4_1—C5_1	169.2 (4)	C1_2—O5_2—C5_2—C6_2	−165.5 (4)
C2_1—C3_1—C4_1—C5_1	49.6 (6)	C1_2—O5_2—C5_2—C4_2	65.9 (5)
C1_1—O5_1—C5_1—C6_1	−171.3 (4)	O1'_2—C4_2—C5_2—O5_2	−178.5 (3)
C1_1—O5_1—C5_1—C4_1	63.5 (5)	C3_2—C4_2—C5_2—O5_2	−57.1 (5)
O1'_1—C4_1—C5_1—O5_1	−175.9 (4)	O1'_2—C4_2—C5_2—C6_2	57.0 (6)
C3_1—C4_1—C5_1—O5_1	−54.3 (5)	C3_2—C4_2—C5_2—C6_2	178.4 (4)
O1'_1—C4_1—C5_1—C6_1	62.2 (5)	C21_2—O6_2—C6_2—C5_2	169.1 (4)
C3_1—C4_1—C5_1—C6_1	−176.2 (4)	O5_2—C5_2—C6_2—O6_2	−66.2 (5)
C21_1—O6_1—C6_1—C5_1	170.4 (4)	C4_2—C5_2—C6_2—O6_2	58.0 (6)
O5_1—C5_1—C6_1—O6_1	−65.7 (5)	C5_2—C4_2—O1'_2—C1'_2	−174.8 (4)
C4_1—C5_1—C6_1—O6_1	57.3 (6)	C3_2—C4_2—O1'_2—C1'_2	66.0 (5)
C3_1—C4_1—O1'_1—C1'_1	64.9 (5)	C4_2—O1'_2—C1'_2—O5'_2	−91.9 (5)
C5_1—C4_1—O1'_1—C1'_1	−174.9 (4)	C4_2—O1'_2—C1'_2—C2'_2	150.7 (4)
C4_1—O1'_1—C1'_1—O5'_1	−90.9 (5)	C5'_2—O5'_2—C1'_2—O1'_2	−177.2 (4)
C4_1—O1'_1—C1'_1—C2'_1	151.4 (4)	C5'_2—O5'_2—C1'_2—C2'_2	−60.8 (5)
C5'_1—O5'_1—C1'_1—O1'_1	−179.7 (4)	C7'_2—O2'_2—C2'_2—C3'_2	−136.5 (4)
C5'_1—O5'_1—C1'_1—C2'_1	−62.5 (5)	C7'_2—O2'_2—C2'_2—C1'_2	105.3 (5)
C7'_1—O2'_1—C2'_1—C3'_1	−136.7 (4)	O1'_2—C1'_2—C2'_2—O2'_2	−73.6 (5)
C7'_1—O2'_1—C2'_1—C1'_1	104.8 (5)	O5'_2—C1'_2—C2'_2—O2'_2	170.2 (4)
O1'_1—C1'_1—C2'_1—O2'_1	−71.5 (5)	O1'_2—C1'_2—C2'_2—C3'_2	171.3 (4)
O5'_1—C1'_1—C2'_1—O2'_1	171.8 (4)	O5'_2—C1'_2—C2'_2—C3'_2	55.1 (5)
O1'_1—C1'_1—C2'_1—C3'_1	171.5 (4)	C14'_2—O3'_2—C3'_2—C4'_2	119.7 (5)
O5'_1—C1'_1—C2'_1—C3'_1	54.9 (5)	C14'_2—O3'_2—C3'_2—C2'_2	−118.0 (5)
C14'_1—O3'_1—C3'_1—C4'_1	122.9 (5)	O2'_2—C2'_2—C3'_2—O3'_2	67.2 (5)
C14'_1—O3'_1—C3'_1—C2'_1	−111.7 (5)	C1'_2—C2'_2—C3'_2—O3'_2	−176.3 (4)
O2'_1—C2'_1—C3'_1—O3'_1	66.9 (5)	O2'_2—C2'_2—C3'_2—C4'_2	−171.0 (4)
C1'_1—C2'_1—C3'_1—O3'_1	−176.0 (4)	C1'_2—C2'_2—C3'_2—C4'_2	−54.5 (6)
O2'_1—C2'_1—C3'_1—C4'_1	−169.8 (4)	C21'_2—O4'_2—C4'_2—C3'_2	−143.6 (4)
C1'_1—C2'_1—C3'_1—C4'_1	−52.7 (6)	C21'_2—O4'_2—C4'_2—C5'_2	98.3 (5)
C21'_1—O4'_1—C4'_1—C3'_1	−135.0 (4)	O3'_2—C3'_2—C4'_2—O4'_2	56.2 (5)
C21'_1—O4'_1—C4'_1—C5'_1	106.8 (5)	C2'_2—C3'_2—C4'_2—O4'_2	−64.4 (5)
O3'_1—C3'_1—C4'_1—O4'_1	56.8 (5)	O3'_2—C3'_2—C4'_2—C5'_2	175.7 (4)
C2'_1—C3'_1—C4'_1—O4'_1	−66.4 (5)	C2'_2—C3'_2—C4'_2—C5'_2	55.2 (5)
O3'_1—C3'_1—C4'_1—C5'_1	176.0 (4)	C1'_2—O5'_2—C5'_2—C6'_2	−173.0 (4)
C2'_1—C3'_1—C4'_1—C5'_1	52.8 (6)	C1'_2—O5'_2—C5'_2—C4'_2	63.6 (5)
C1'_1—O5'_1—C5'_1—C6'_1	−171.2 (4)	O4'_2—C4'_2—C5'_2—O5'_2	60.3 (5)
C1'_1—O5'_1—C5'_1—C4'_1	64.2 (5)	C3'_2—C4'_2—C5'_2—O5'_2	−58.6 (5)
O4'_1—C4'_1—C5'_1—O5'_1	61.8 (5)	O4'_2—C4'_2—C5'_2—C6'_2	−58.6 (6)
C3'_1—C4'_1—C5'_1—O5'_1	−56.8 (5)	C3'_2—C4'_2—C5'_2—C6'_2	−177.5 (4)
O4'_1—C4'_1—C5'_1—C6'_1	−58.4 (6)	C28'_2—O6'_2—C6'_2—C5'_2	177.8 (4)
C3'_1—C4'_1—C5'_1—C6'_1	−177.0 (4)	O5'_2—C5'_2—C6'_2—O6'_2	68.5 (5)
C28'_1—O6'_1—C6'_1—C5'_1	179.1 (4)	C4'_2—C5'_2—C6'_2—O6'_2	−170.3 (4)
O5'_1—C5'_1—C6'_1—O6'_1	67.8 (5)	C1_2—O1_2—C7_2—O7_2	3.8 (8)
C4'_1—C5'_1—C6'_1—O6'_1	−170.3 (4)	C1_2—O1_2—C7_2—C8_2	−176.5 (4)
C1_1—O1_1—C7_1—O7_1	13.4 (8)	O7_2—C7_2—C8_2—C9_2	164.8 (6)
C1_1—O1_1—C7_1—C8_1	−164.4 (4)	O1_2—C7_2—C8_2—C9_2	−14.9 (8)
O7_1—C7_1—C8_1—C13_1	−9.3 (9)	O7_2—C7_2—C8_2—C13_2	−16.0 (9)
O1_1—C7_1—C8_1—C13_1	168.5 (5)	O1_2—C7_2—C8_2—C13_2	164.3 (5)
O7_1—C7_1—C8_1—C9_1	174.0 (6)	C13_2—C8_2—C9_2—C10_2	1.8 (9)
O1_1—C7_1—C8_1—C9_1	−8.2 (8)	C7_2—C8_2—C9_2—C10_2	−179.0 (6)
C13_1—C8_1—C9_1—C10_1	−0.4 (9)	C8_2—C9_2—C10_2—C11_2	−2.0 (10)
C7_1—C8_1—C9_1—C10_1	176.2 (6)	C9_2—C10_2—C11_2—C12_2	1.0 (10)
C8_1—C9_1—C10_1—C11_1	−0.8 (10)	C10_2—C11_2—C12_2—C13_2	0.2 (10)
C9_1—C10_1—C11_1—C12_1	1.5 (11)	C9_2—C8_2—C13_2—C12_2	−0.6 (8)
C10_1—C11_1—C12_1—C13_1	−1.0 (10)	C7_2—C8_2—C13_2—C12_2	−179.9 (5)
C11_1—C12_1—C13_1—C8_1	−0.2 (9)	C11_2—C12_2—C13_2—C8_2	−0.4 (9)
C9_1—C8_1—C13_1—C12_1	0.9 (8)	C2_2—O2_2—C14_2—O8_2	16.5 (8)
C7_1—C8_1—C13_1—C12_1	−175.9 (5)	C2_2—O2_2—C14_2—C15_2	−162.9 (4)
C2_1—O2_1—C14_1—O8_1	16.2 (8)	O8_2—C14_2—C15_2—C16_2	−163.8 (6)
C2_1—O2_1—C14_1—C15_1	−163.5 (4)	O2_2—C14_2—C15_2—C16_2	15.6 (8)
O8_1—C14_1—C15_1—C16_1	−173.2 (6)	O8_2—C14_2—C15_2—C20_2	12.7 (9)
O2_1—C14_1—C15_1—C16_1	6.5 (7)	O2_2—C14_2—C15_2—C20_2	−167.9 (5)
O8_1—C14_1—C15_1—C20_1	3.9 (9)	C20_2—C15_2—C16_2—C17_2	−1.6 (9)
O2_1—C14_1—C15_1—C20_1	−176.4 (5)	C14_2—C15_2—C16_2—C17_2	174.9 (6)
C20_1—C15_1—C16_1—C17_1	1.9 (9)	C15_2—C16_2—C17_2—C18_2	0.8 (10)
C14_1—C15_1—C16_1—C17_1	179.0 (5)	C16_2—C17_2—C18_2—C19_2	1.3 (11)
C15_1—C16_1—C17_1—C18_1	−0.4 (9)	C17_2—C18_2—C19_2—C20_2	−2.4 (12)
C16_1—C17_1—C18_1—C19_1	−0.8 (11)	C16_2—C15_2—C20_2—C19_2	0.4 (10)
C17_1—C18_1—C19_1—C20_1	0.6 (11)	C14_2—C15_2—C20_2—C19_2	−176.2 (6)
C18_1—C19_1—C20_1—C15_1	0.8 (10)	C18_2—C19_2—C20_2—C15_2	1.6 (11)
C16_1—C15_1—C20_1—C19_1	−2.1 (9)	C6_2—O6_2—C21_2—O9_2	1.5 (7)
C14_1—C15_1—C20_1—C19_1	−179.3 (6)	C6_2—O6_2—C21_2—C22_2	−176.0 (4)
C6_1—O6_1—C21_1—O9_1	1.7 (7)	O9_2—C21_2—C22_2—C23_2	−179.3 (6)
C6_1—O6_1—C21_1—C22_1	−177.9 (4)	O6_2—C21_2—C22_2—C23_2	−1.8 (7)
O9_1—C21_1—C22_1—C23_1	176.7 (6)	O9_2—C21_2—C22_2—C27_2	0.4 (8)
O6_1—C21_1—C22_1—C23_1	−3.7 (7)	O6_2—C21_2—C22_2—C27_2	177.8 (5)
O9_1—C21_1—C22_1—C27_1	−4.6 (8)	C27_2—C22_2—C23_2—C24_2	−2.2 (9)
O6_1—C21_1—C22_1—C27_1	175.1 (5)	C21_2—C22_2—C23_2—C24_2	177.4 (5)
C27_1—C22_1—C23_1—C24_1	−1.3 (9)	C22_2—C23_2—C24_2—C25_2	1.7 (9)
C21_1—C22_1—C23_1—C24_1	177.5 (6)	C23_2—C24_2—C25_2—C26_2	−0.4 (9)
C22_1—C23_1—C24_1—C25_1	1.2 (10)	C24_2—C25_2—C26_2—C27_2	−0.3 (10)
C23_1—C24_1—C25_1—C26_1	−0.7 (11)	C25_2—C26_2—C27_2—C22_2	−0.3 (9)
C24_1—C25_1—C26_1—C27_1	0.2 (11)	C23_2—C22_2—C27_2—C26_2	1.5 (9)
C23_1—C22_1—C27_1—C26_1	0.8 (9)	C21_2—C22_2—C27_2—C26_2	−178.2 (5)
C21_1—C22_1—C27_1—C26_1	−178.0 (5)	C2'_2—O2'_2—C7'_2—O7'_2	0.7 (7)
C25_1—C26_1—C27_1—C22_1	−0.3 (9)	C2'_2—O2'_2—C7'_2—C8'_2	−179.8 (4)
C2'_1—O2'_1—C7'_1—O7'_1	2.1 (8)	O7'_2—C7'_2—C8'_2—C9'_2	−159.4 (6)
C2'_1—O2'_1—C7'_1—C8'_1	−177.7 (4)	O2'_2—C7'_2—C8'_2—C9'_2	21.2 (7)
O7'_1—C7'_1—C8'_1—C9'_1	−163.8 (5)	O7'_2—C7'_2—C8'_2—C13'_2	20.4 (8)
O2'_1—C7'_1—C8'_1—C9'_1	16.0 (7)	O2'_2—C7'_2—C8'_2—C13'_2	−159.1 (5)
O7'_1—C7'_1—C8'_1—C13'_1	15.0 (8)	C13'_2—C8'_2—C9'_2—C10'_2	0.0 (9)
O2'_1—C7'_1—C8'_1—C13'_1	−165.1 (5)	C7'_2—C8'_2—C9'_2—C10'_2	179.8 (5)
C13'_1—C8'_1—C9'_1—C10'_1	0.5 (8)	C8'_2—C9'_2—C10'_2—C11'_2	1.3 (9)
C7'_1—C8'_1—C9'_1—C10'_1	179.4 (5)	C9'_2—C10'_2—C11'_2—C12'_2	−1.5 (11)
C8'_1—C9'_1—C10'_1—C11'_1	0.3 (8)	C10'_2—C11'_2—C12'_2—C13'_2	0.4 (13)
C9'_1—C10'_1—C11'_1—C12'_1	−0.4 (9)	C11'_2—C12'_2—C13'_2—C8'_2	1.0 (12)
C10'_1—C11'_1—C12'_1—C13'_1	−0.4 (10)	C9'_2—C8'_2—C13'_2—C12'_2	−1.2 (10)
C11'_1—C12'_1—C13'_1—C8'_1	1.2 (10)	C7'_2—C8'_2—C13'_2—C12'_2	179.0 (6)
C9'_1—C8'_1—C13'_1—C12'_1	−1.3 (9)	C3'_2—O3'_2—C14'_2—O8'_2	−6.1 (7)
C7'_1—C8'_1—C13'_1—C12'_1	179.8 (6)	C3'_2—O3'_2—C14'_2—C15'_2	173.8 (4)
C3'_1—O3'_1—C14'_1—O8'_1	−3.6 (7)	O8'_2—C14'_2—C15'_2—C16'_2	−176.2 (5)
C3'_1—O3'_1—C14'_1—C15'_1	176.4 (4)	O3'_2—C14'_2—C15'_2—C16'_2	3.9 (7)
O8'_1—C14'_1—C15'_1—C16'_1	−178.6 (6)	O8'_2—C14'_2—C15'_2—C20'_2	5.0 (8)
O3'_1—C14'_1—C15'_1—C16'_1	1.4 (7)	O3'_2—C14'_2—C15'_2—C20'_2	−174.8 (4)
O8'_1—C14'_1—C15'_1—C20'_1	3.1 (8)	C20'_2—C15'_2—C16'_2—C17'_2	−1.1 (8)
O3'_1—C14'_1—C15'_1—C20'_1	−176.9 (5)	C14'_2—C15'_2—C16'_2—C17'_2	−179.8 (5)
C20'_1—C15'_1—C16'_1—C17'_1	0.5 (9)	C15'_2—C16'_2—C17'_2—C18'_2	2.0 (9)
C14'_1—C15'_1—C16'_1—C17'_1	−177.9 (6)	C16'_2—C17'_2—C18'_2—C19'_2	−1.9 (9)
C15'_1—C16'_1—C17'_1—C18'_1	0.7 (10)	C17'_2—C18'_2—C19'_2—C20'_2	0.9 (10)
C16'_1—C17'_1—C18'_1—C19'_1	−0.9 (10)	C18'_2—C19'_2—C20'_2—C15'_2	0.0 (9)
C17'_1—C18'_1—C19'_1—C20'_1	0.1 (11)	C16'_2—C15'_2—C20'_2—C19'_2	0.1 (8)
C18'_1—C19'_1—C20'_1—C15'_1	1.1 (10)	C14'_2—C15'_2—C20'_2—C19'_2	178.9 (5)
C16'_1—C15'_1—C20'_1—C19'_1	−1.3 (9)	C4'_2—O4'_2—C21'_2—O9'_2	0.8 (7)
C14'_1—C15'_1—C20'_1—C19'_1	177.1 (6)	C4'_2—O4'_2—C21'_2—C22'_2	−178.4 (4)
C4'_1—O4'_1—C21'_1—O9'_1	−1.6 (7)	O9'_2—C21'_2—C22'_2—C23'_2	−173.4 (6)
C4'_1—O4'_1—C21'_1—C22'_1	179.4 (4)	O4'_2—C21'_2—C22'_2—C23'_2	5.8 (7)
O9'_1—C21'_1—C22'_1—C27'_1	3.4 (8)	O9'_2—C21'_2—C22'_2—C27'_2	7.0 (8)
O4'_1—C21'_1—C22'_1—C27'_1	−177.5 (4)	O4'_2—C21'_2—C22'_2—C27'_2	−173.8 (5)
O9'_1—C21'_1—C22'_1—C23'_1	−177.2 (6)	C27'_2—C22'_2—C23'_2—C24'_2	−0.3 (9)
O4'_1—C21'_1—C22'_1—C23'_1	1.8 (7)	C21'_2—C22'_2—C23'_2—C24'_2	−179.8 (5)
C27'_1—C22'_1—C23'_1—C24'_1	0.5 (8)	C22'_2—C23'_2—C24'_2—C25'_2	0.9 (10)
C21'_1—C22'_1—C23'_1—C24'_1	−178.8 (5)	C23'_2—C24'_2—C25'_2—C26'_2	−1.6 (10)
C22'_1—C23'_1—C24'_1—C25'_1	−0.1 (8)	C24'_2—C25'_2—C26'_2—C27'_2	1.5 (10)
C23'_1—C24'_1—C25'_1—C26'_1	−0.6 (8)	C25'_2—C26'_2—C27'_2—C22'_2	−0.9 (9)
C24'_1—C25'_1—C26'_1—C27'_1	0.9 (8)	C23'_2—C22'_2—C27'_2—C26'_2	0.2 (8)
C25'_1—C26'_1—C27'_1—C22'_1	−0.6 (8)	C21'_2—C22'_2—C27'_2—C26'_2	179.8 (5)
C23'_1—C22'_1—C27'_1—C26'_1	−0.1 (8)	C6'_2—O6'_2—C28'_2—O10'_2	7.0 (7)
C21'_1—C22'_1—C27'_1—C26'_1	179.2 (5)	C6'_2—O6'_2—C28'_2—C29'_2	−172.6 (4)
C6'_1—O6'_1—C28'_1—O10'_1	1.7 (7)	O10'_2—C28'_2—C29'_2—C34'_2	−13.1 (8)
C6'_1—O6'_1—C28'_1—C29'_1	179.8 (4)	O6'_2—C28'_2—C29'_2—C34'_2	166.5 (5)
O10'_1—C28'_1—C29'_1—C30'_1	−176.4 (5)	O10'_2—C28'_2—C29'_2—C30'_2	171.2 (5)
O6'_1—C28'_1—C29'_1—C30'_1	5.6 (7)	O6'_2—C28'_2—C29'_2—C30'_2	−9.3 (7)
O10'_1—C28'_1—C29'_1—C34'_1	4.0 (8)	C34'_2—C29'_2—C30'_2—C31'_2	−0.8 (9)
O6'_1—C28'_1—C29'_1—C34'_1	−174.1 (5)	C28'_2—C29'_2—C30'_2—C31'_2	174.9 (5)
C34'_1—C29'_1—C30'_1—C31'_1	−1.5 (8)	C29'_2—C30'_2—C31'_2—C32'_2	−2.0 (9)
C28'_1—C29'_1—C30'_1—C31'_1	178.8 (5)	C30'_2—C31'_2—C32'_2—C33'_2	2.9 (10)
C29'_1—C30'_1—C31'_1—C32'_1	1.9 (9)	C31'_2—C32'_2—C33'_2—C34'_2	−0.9 (11)
C30'_1—C31'_1—C32'_1—C33'_1	−2.2 (10)	C32'_2—C33'_2—C34'_2—C29'_2	−1.9 (11)
C31'_1—C32'_1—C33'_1—C34'_1	2.1 (10)	C30'_2—C29'_2—C34'_2—C33'_2	2.8 (10)
C30'_1—C29'_1—C34'_1—C33'_1	1.4 (8)	C28'_2—C29'_2—C34'_2—C33'_2	−173.1 (6)
C28'_1—C29'_1—C34'_1—C33'_1	−178.9 (5)	C3S_3—O2S_3—C2S_3—O1S_3	−1.1 (11)
C32'_1—C33'_1—C34'_1—C29'_1	−1.7 (9)	C3S_3—O2S_3—C2S_3—C1S_3	−179.5 (7)
C7_2—O1_2—C1_2—O5_2	−133.6 (4)	C2S_3—O2S_3—C3S_3—C4S_3	179.9 (6)
C7_2—O1_2—C1_2—C2_2	108.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3_1—H3O_1···O5′_1	0.79 (7)	2.32 (7)	2.797 (5)	120 (6)
O3_1—H3O_1···O6′_1	0.79 (7)	2.39 (7)	3.147 (6)	160 (6)
O3_2—H3O_2···O5′_2	0.73 (7)	2.19 (7)	2.806 (5)	142 (7)
O3_2—H3O_2···O6′_2	0.73 (7)	2.62 (7)	3.256 (5)	146 (6)

1,2,4,6-Tetra-O-benzoyl-β-D-glucopyranose acetone monosolvate (IV) top

Crystal data top

C₃₄H₂₈O₁₀·C₃H₆O	D_x = 1.305 Mg m⁻³
M_r = 654.64	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9756 reflections
a = 5.6342 (2) Å	θ = 3.7–72.1°
b = 19.9711 (8) Å	µ = 0.80 mm⁻¹
c = 29.6094 (11) Å	T = 120 K
V = 3331.7 (2) Å³	Needle, colorless
Z = 4	0.21 × 0.13 × 0.09 mm
F(000) = 1376

Data collection top

Bruker APEXII diffractometer	6526 independent reflections
Radiation source: Incoatec micro-focus	6458 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	R_int = 0.031
combination of ω and φ–scans	θ_max = 72.2°, θ_min = 2.7°
Absorption correction: numerical (SADABS; Krause et al., 2015)	h = −6→6
T_min = 0.817, T_max = 0.864	k = −24→24
55150 measured reflections	l = −36→36

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)] = 0.028	H-atom parameters constrained
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0468P)² + 0.4158P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
6526 reflections	Δρ_max = 0.16 e Å⁻³
436 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 2722 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: real-space vector search	Absolute structure parameter: −0.08 (3)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.71598 (19)	0.61168 (5)	0.67190 (3)	0.0214 (2)
O2	0.51227 (19)	0.51317 (5)	0.73044 (3)	0.0213 (2)
O3	0.1940 (2)	0.42653 (6)	0.68429 (4)	0.0281 (2)
H3	0.1978	0.3853	0.6900	0.042*
O4	0.3962 (2)	0.37642 (5)	0.60127 (4)	0.0232 (2)
O5	0.66468 (19)	0.54186 (5)	0.61282 (3)	0.0215 (2)
O6	0.4464 (2)	0.52909 (6)	0.53425 (3)	0.0256 (2)
O7	1.0761 (2)	0.61400 (6)	0.63814 (3)	0.0251 (2)
O8	0.1803 (2)	0.57306 (7)	0.74478 (4)	0.0355 (3)
O9	0.0840 (2)	0.39447 (6)	0.55505 (4)	0.0339 (3)
O10	0.5742 (2)	0.53514 (6)	0.46280 (4)	0.0323 (3)
C1	0.6951 (3)	0.54302 (7)	0.66012 (5)	0.0195 (3)
H1	0.8379	0.5168	0.6696	0.023*
C2	0.4708 (3)	0.51718 (7)	0.68248 (4)	0.0192 (3)
H2	0.3348	0.5479	0.6760	0.023*
C3	0.4149 (3)	0.44667 (7)	0.66592 (5)	0.0208 (3)
H3A	0.5416	0.4154	0.6766	0.025*
C4	0.4086 (3)	0.44620 (7)	0.61448 (5)	0.0208 (3)
H4	0.2671	0.4713	0.6031	0.025*
C5	0.6368 (3)	0.47582 (7)	0.59525 (5)	0.0208 (3)
H5	0.7749	0.4476	0.6046	0.025*
C6	0.6350 (3)	0.48287 (8)	0.54450 (5)	0.0238 (3)
H6A	0.7891	0.5005	0.5336	0.029*
H6B	0.6054	0.4390	0.5300	0.029*
C7	0.9167 (3)	0.64249 (8)	0.65719 (5)	0.0209 (3)
C8	0.9126 (3)	0.71557 (8)	0.66667 (5)	0.0240 (3)
C9	1.1059 (3)	0.75298 (9)	0.65200 (6)	0.0344 (4)
H9	1.2339	0.7316	0.6369	0.041*
C10	1.1118 (4)	0.82151 (10)	0.65945 (8)	0.0445 (5)
H10	1.2439	0.8471	0.6495	0.053*
C11	0.9252 (4)	0.85264 (9)	0.68140 (7)	0.0407 (4)
H11	0.9299	0.8996	0.6866	0.049*
C12	0.7315 (4)	0.81563 (9)	0.69585 (6)	0.0366 (4)
H12	0.6037	0.8373	0.7108	0.044*
C13	0.7236 (3)	0.74696 (8)	0.68851 (6)	0.0291 (3)
H13	0.5905	0.7216	0.6983	0.035*
C14	0.3477 (3)	0.54065 (7)	0.75764 (5)	0.0213 (3)
C15	0.3993 (3)	0.52627 (7)	0.80603 (5)	0.0201 (3)
C16	0.6103 (3)	0.49601 (8)	0.81988 (5)	0.0235 (3)
H16	0.7268	0.4836	0.7982	0.028*
C17	0.6491 (3)	0.48408 (8)	0.86556 (5)	0.0253 (3)
H17	0.7941	0.4645	0.8752	0.030*
C18	0.4763 (3)	0.50067 (8)	0.89711 (5)	0.0255 (3)
H18	0.5023	0.4916	0.9282	0.031*
C19	0.2661 (3)	0.53037 (8)	0.88333 (5)	0.0280 (3)
H19	0.1481	0.5416	0.9050	0.034*
C20	0.2280 (3)	0.54381 (8)	0.83777 (5)	0.0242 (3)
H20	0.0853	0.5649	0.8284	0.029*
C21	0.2212 (3)	0.35697 (8)	0.57317 (5)	0.0222 (3)
C22	0.2203 (3)	0.28273 (8)	0.56731 (5)	0.0218 (3)
C23	0.4016 (3)	0.24286 (8)	0.58459 (5)	0.0263 (3)
H23	0.5296	0.2627	0.6006	0.032*
C24	0.3942 (3)	0.17400 (8)	0.57828 (6)	0.0302 (3)
H24	0.5192	0.1468	0.5896	0.036*
C25	0.2053 (3)	0.14467 (8)	0.55555 (5)	0.0286 (3)
H25	0.1999	0.0975	0.5517	0.034*
C26	0.0243 (3)	0.18441 (9)	0.53847 (5)	0.0289 (3)
H26	−0.1051	0.1643	0.5230	0.035*
C27	0.0317 (3)	0.25358 (8)	0.54393 (5)	0.0264 (3)
H27	−0.0910	0.2808	0.5318	0.032*
C28	0.4428 (3)	0.55396 (8)	0.49223 (5)	0.0231 (3)
C29	0.2557 (3)	0.60598 (8)	0.48703 (5)	0.0237 (3)
C30	0.0917 (3)	0.61948 (8)	0.52115 (5)	0.0271 (3)
H30	0.1010	0.5965	0.5492	0.033*
C31	−0.0851 (3)	0.66670 (9)	0.51390 (7)	0.0355 (4)
H31	−0.1985	0.6755	0.5369	0.043*
C32	−0.0971 (4)	0.70125 (9)	0.47316 (7)	0.0397 (4)
H32	−0.2187	0.7334	0.4683	0.048*
C33	0.0697 (4)	0.68854 (9)	0.43959 (6)	0.0380 (4)
H33	0.0633	0.7126	0.4119	0.046*
C34	0.2455 (3)	0.64079 (9)	0.44633 (5)	0.0307 (3)
H34	0.3584	0.6319	0.4233	0.037*
O11	0.2960 (3)	0.29141 (6)	0.69577 (5)	0.0383 (3)
C35	0.1682 (3)	0.24299 (9)	0.69602 (6)	0.0349 (4)
C36	0.2618 (4)	0.17400 (9)	0.70283 (7)	0.0398 (4)
H36A	0.2532	0.1492	0.6743	0.060*
H36B	0.1664	0.1510	0.7258	0.060*
H36C	0.4272	0.1764	0.7129	0.060*
C37	−0.0913 (6)	0.24957 (19)	0.6894 (2)	0.1159 (18)
H37A	−0.1729	0.2409	0.7181	0.174*
H37B	−0.1445	0.2171	0.6668	0.174*
H37C	−0.1284	0.2950	0.6791	0.174*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0222 (5)	0.0199 (5)	0.0220 (5)	0.0000 (4)	0.0021 (4)	−0.0020 (4)
O2	0.0219 (5)	0.0242 (5)	0.0178 (5)	0.0048 (4)	0.0011 (4)	0.0010 (4)
O3	0.0287 (6)	0.0220 (5)	0.0337 (5)	−0.0030 (5)	0.0079 (5)	0.0023 (4)
O4	0.0250 (5)	0.0169 (5)	0.0277 (5)	0.0022 (4)	−0.0042 (4)	−0.0021 (4)
O5	0.0285 (5)	0.0182 (5)	0.0176 (4)	−0.0002 (4)	0.0014 (4)	0.0001 (4)
O6	0.0289 (6)	0.0288 (5)	0.0190 (5)	0.0077 (5)	0.0030 (4)	0.0028 (4)
O7	0.0232 (5)	0.0271 (5)	0.0249 (5)	0.0030 (4)	0.0016 (4)	0.0036 (4)
O8	0.0351 (7)	0.0487 (7)	0.0228 (5)	0.0217 (6)	0.0009 (5)	0.0009 (5)
O9	0.0341 (6)	0.0278 (6)	0.0398 (6)	0.0097 (5)	−0.0133 (5)	−0.0062 (5)
O10	0.0380 (7)	0.0403 (6)	0.0185 (5)	0.0095 (6)	0.0024 (5)	−0.0026 (4)
C1	0.0222 (6)	0.0185 (6)	0.0179 (6)	0.0021 (5)	0.0003 (5)	−0.0006 (5)
C2	0.0212 (7)	0.0197 (6)	0.0167 (6)	0.0028 (5)	0.0001 (5)	0.0010 (5)
C3	0.0218 (7)	0.0186 (6)	0.0219 (6)	0.0018 (6)	0.0018 (6)	0.0016 (5)
C4	0.0238 (7)	0.0165 (6)	0.0222 (6)	0.0030 (6)	−0.0010 (6)	−0.0011 (5)
C5	0.0238 (7)	0.0183 (6)	0.0203 (6)	0.0029 (6)	0.0003 (5)	−0.0023 (5)
C6	0.0265 (7)	0.0234 (7)	0.0215 (7)	0.0050 (6)	0.0006 (6)	−0.0014 (5)
C7	0.0209 (7)	0.0245 (7)	0.0174 (6)	−0.0008 (6)	−0.0036 (5)	0.0026 (5)
C8	0.0260 (7)	0.0239 (7)	0.0220 (6)	−0.0014 (6)	−0.0043 (6)	0.0027 (5)
C9	0.0283 (8)	0.0288 (8)	0.0462 (10)	−0.0021 (7)	0.0016 (8)	0.0034 (7)
C10	0.0371 (10)	0.0277 (9)	0.0687 (13)	−0.0086 (8)	−0.0016 (10)	0.0071 (8)
C11	0.0463 (11)	0.0211 (7)	0.0548 (11)	−0.0025 (8)	−0.0092 (9)	−0.0004 (7)
C12	0.0419 (10)	0.0280 (8)	0.0401 (9)	0.0048 (8)	−0.0007 (8)	−0.0046 (7)
C13	0.0312 (8)	0.0252 (7)	0.0308 (8)	−0.0001 (6)	0.0010 (7)	0.0000 (6)
C14	0.0216 (7)	0.0199 (6)	0.0222 (7)	0.0019 (5)	0.0012 (5)	−0.0010 (5)
C15	0.0218 (7)	0.0175 (6)	0.0210 (6)	−0.0012 (5)	0.0005 (6)	−0.0005 (5)
C16	0.0239 (7)	0.0231 (6)	0.0237 (7)	0.0024 (6)	0.0002 (6)	−0.0010 (5)
C17	0.0272 (8)	0.0237 (7)	0.0251 (7)	0.0015 (6)	−0.0045 (6)	0.0000 (6)
C18	0.0332 (8)	0.0242 (7)	0.0189 (6)	−0.0060 (6)	−0.0019 (6)	0.0009 (5)
C19	0.0303 (8)	0.0312 (8)	0.0223 (7)	−0.0026 (6)	0.0053 (6)	−0.0017 (6)
C20	0.0226 (7)	0.0256 (7)	0.0243 (7)	0.0010 (6)	0.0020 (6)	−0.0012 (6)
C21	0.0209 (7)	0.0245 (7)	0.0211 (6)	0.0038 (6)	0.0008 (6)	−0.0028 (6)
C22	0.0230 (7)	0.0230 (7)	0.0195 (6)	0.0001 (6)	0.0027 (5)	−0.0019 (5)
C23	0.0255 (7)	0.0231 (7)	0.0302 (7)	0.0016 (6)	−0.0045 (6)	−0.0032 (6)
C24	0.0331 (8)	0.0219 (7)	0.0355 (8)	0.0024 (7)	−0.0047 (7)	−0.0005 (6)
C25	0.0361 (8)	0.0224 (7)	0.0272 (7)	−0.0037 (7)	0.0014 (7)	−0.0025 (6)
C26	0.0299 (8)	0.0312 (8)	0.0255 (7)	−0.0074 (7)	−0.0022 (6)	−0.0041 (6)
C27	0.0237 (7)	0.0298 (8)	0.0256 (7)	0.0010 (6)	−0.0006 (6)	−0.0022 (6)
C28	0.0279 (7)	0.0242 (7)	0.0172 (6)	−0.0017 (6)	−0.0011 (6)	−0.0026 (5)
C29	0.0278 (8)	0.0212 (7)	0.0220 (6)	−0.0029 (6)	−0.0044 (6)	−0.0015 (5)
C30	0.0288 (8)	0.0241 (7)	0.0283 (7)	−0.0005 (7)	0.0000 (6)	0.0000 (6)
C31	0.0308 (9)	0.0308 (8)	0.0448 (9)	0.0035 (8)	0.0012 (8)	−0.0015 (7)
C32	0.0369 (10)	0.0294 (8)	0.0528 (11)	0.0056 (8)	−0.0117 (9)	0.0026 (8)
C33	0.0473 (11)	0.0308 (8)	0.0357 (8)	0.0002 (8)	−0.0134 (8)	0.0068 (7)
C34	0.0389 (9)	0.0292 (8)	0.0239 (7)	−0.0018 (7)	−0.0049 (7)	0.0014 (6)
O11	0.0435 (7)	0.0255 (6)	0.0458 (7)	−0.0043 (5)	0.0052 (6)	0.0050 (5)
C35	0.0348 (10)	0.0321 (9)	0.0378 (9)	−0.0051 (7)	0.0007 (7)	0.0040 (7)
C36	0.0462 (11)	0.0269 (8)	0.0463 (10)	−0.0079 (8)	0.0055 (9)	0.0034 (7)
C37	0.0391 (15)	0.0708 (19)	0.238 (6)	−0.0009 (14)	−0.028 (2)	0.024 (3)

Geometric parameters (Å, º) top

O1—C7	1.3591 (19)	C16—C17	1.391 (2)
O1—C1	1.4197 (17)	C16—H16	0.9500
O2—C14	1.3451 (18)	C17—C18	1.389 (2)
O2—C2	1.4414 (16)	C17—H17	0.9500
O3—C3	1.4163 (18)	C18—C19	1.386 (2)
O3—H3	0.8400	C18—H18	0.9500
O4—C21	1.3473 (19)	C19—C20	1.392 (2)
O4—C4	1.4492 (16)	C19—H19	0.9500
O5—C1	1.4110 (16)	C20—H20	0.9500
O5—C5	1.4266 (17)	C21—C22	1.493 (2)
O6—C28	1.3399 (18)	C22—C23	1.393 (2)
O6—C6	1.4401 (19)	C22—C27	1.395 (2)
O7—C7	1.2036 (19)	C23—C24	1.388 (2)
O8—C14	1.206 (2)	C23—H23	0.9500
O9—C21	1.202 (2)	C24—C25	1.389 (2)
O10—C28	1.204 (2)	C24—H24	0.9500
C1—C2	1.517 (2)	C25—C26	1.388 (3)
C1—H1	1.0000	C25—H25	0.9500
C2—C3	1.5240 (19)	C26—C27	1.391 (2)
C2—H2	1.0000	C26—H26	0.9500
C3—C4	1.5235 (18)	C27—H27	0.9500
C3—H3A	1.0000	C28—C29	1.488 (2)
C4—C5	1.526 (2)	C29—C34	1.392 (2)
C4—H4	1.0000	C29—C30	1.395 (2)
C5—C6	1.5094 (18)	C30—C31	1.388 (2)
C5—H5	1.0000	C30—H30	0.9500
C6—H6A	0.9900	C31—C32	1.392 (3)
C6—H6B	0.9900	C31—H31	0.9500
C7—C8	1.486 (2)	C32—C33	1.391 (3)
C8—C9	1.390 (2)	C32—H32	0.9500
C8—C13	1.395 (2)	C33—C34	1.390 (3)
C9—C10	1.387 (3)	C33—H33	0.9500
C9—H9	0.9500	C34—H34	0.9500
C10—C11	1.383 (3)	O11—C35	1.206 (2)
C10—H10	0.9500	C35—C37	1.481 (4)
C11—C12	1.386 (3)	C35—C36	1.489 (3)
C11—H11	0.9500	C36—H36A	0.9800
C12—C13	1.389 (2)	C36—H36B	0.9800
C12—H12	0.9500	C36—H36C	0.9800
C13—H13	0.9500	C37—H37A	0.9800
C14—C15	1.4897 (19)	C37—H37B	0.9800
C15—C20	1.392 (2)	C37—H37C	0.9800
C15—C16	1.395 (2)

C7—O1—C1	115.31 (11)	C15—C16—H16	120.2
C14—O2—C2	117.11 (11)	C18—C17—C16	120.21 (15)
C3—O3—H3	109.5	C18—C17—H17	119.9
C21—O4—C4	118.65 (11)	C16—C17—H17	119.9
C1—O5—C5	112.99 (11)	C19—C18—C17	120.18 (14)
C28—O6—C6	116.39 (12)	C19—C18—H18	119.9
O5—C1—O1	105.65 (11)	C17—C18—H18	119.9
O5—C1—C2	109.05 (12)	C18—C19—C20	119.97 (15)
O1—C1—C2	106.88 (11)	C18—C19—H19	120.0
O5—C1—H1	111.7	C20—C19—H19	120.0
O1—C1—H1	111.7	C15—C20—C19	119.94 (15)
C2—C1—H1	111.7	C15—C20—H20	120.0
O2—C2—C1	108.30 (11)	C19—C20—H20	120.0
O2—C2—C3	107.40 (11)	O9—C21—O4	124.49 (14)
C1—C2—C3	110.26 (11)	O9—C21—C22	124.36 (15)
O2—C2—H2	110.3	O4—C21—C22	111.15 (13)
C1—C2—H2	110.3	C23—C22—C27	120.15 (14)
C3—C2—H2	110.3	C23—C22—C21	121.50 (14)
O3—C3—C4	111.21 (12)	C27—C22—C21	118.34 (14)
O3—C3—C2	108.70 (12)	C24—C23—C22	119.67 (15)
C4—C3—C2	109.39 (11)	C24—C23—H23	120.2
O3—C3—H3A	109.2	C22—C23—H23	120.2
C4—C3—H3A	109.2	C23—C24—C25	120.38 (16)
C2—C3—H3A	109.2	C23—C24—H24	119.8
O4—C4—C3	106.08 (11)	C25—C24—H24	119.8
O4—C4—C5	108.22 (11)	C26—C25—C24	119.91 (15)
C3—C4—C5	110.57 (12)	C26—C25—H25	120.0
O4—C4—H4	110.6	C24—C25—H25	120.0
C3—C4—H4	110.6	C25—C26—C27	120.22 (15)
C5—C4—H4	110.6	C25—C26—H26	119.9
O5—C5—C6	106.11 (11)	C27—C26—H26	119.9
O5—C5—C4	108.36 (11)	C26—C27—C22	119.65 (15)
C6—C5—C4	113.72 (13)	C26—C27—H27	120.2
O5—C5—H5	109.5	C22—C27—H27	120.2
C6—C5—H5	109.5	O10—C28—O6	123.18 (15)
C4—C5—H5	109.5	O10—C28—C29	125.38 (14)
O6—C6—C5	105.94 (11)	O6—C28—C29	111.44 (13)
O6—C6—H6A	110.5	C34—C29—C30	120.20 (16)
C5—C6—H6A	110.5	C34—C29—C28	117.85 (15)
O6—C6—H6B	110.5	C30—C29—C28	121.95 (14)
C5—C6—H6B	110.5	C31—C30—C29	119.63 (15)
H6A—C6—H6B	108.7	C31—C30—H30	120.2
O7—C7—O1	123.86 (14)	C29—C30—H30	120.2
O7—C7—C8	124.34 (14)	C30—C31—C32	120.38 (18)
O1—C7—C8	111.79 (13)	C30—C31—H31	119.8
C9—C8—C13	120.09 (15)	C32—C31—H31	119.8
C9—C8—C7	117.17 (15)	C33—C32—C31	119.75 (17)
C13—C8—C7	122.72 (15)	C33—C32—H32	120.1
C10—C9—C8	119.96 (18)	C31—C32—H32	120.1
C10—C9—H9	120.0	C34—C33—C32	120.28 (16)
C8—C9—H9	120.0	C34—C33—H33	119.9
C11—C10—C9	120.02 (18)	C32—C33—H33	119.9
C11—C10—H10	120.0	C33—C34—C29	119.75 (17)
C9—C10—H10	120.0	C33—C34—H34	120.1
C10—C11—C12	120.25 (17)	C29—C34—H34	120.1
C10—C11—H11	119.9	O11—C35—C37	121.2 (2)
C12—C11—H11	119.9	O11—C35—C36	122.09 (19)
C11—C12—C13	120.23 (18)	C37—C35—C36	116.7 (2)
C11—C12—H12	119.9	C35—C36—H36A	109.5
C13—C12—H12	119.9	C35—C36—H36B	109.5
C12—C13—C8	119.45 (17)	H36A—C36—H36B	109.5
C12—C13—H13	120.3	C35—C36—H36C	109.5
C8—C13—H13	120.3	H36A—C36—H36C	109.5
O8—C14—O2	124.68 (13)	H36B—C36—H36C	109.5
O8—C14—C15	124.04 (14)	C35—C37—H37A	109.5
O2—C14—C15	111.28 (12)	C35—C37—H37B	109.5
C20—C15—C16	120.08 (14)	H37A—C37—H37B	109.5
C20—C15—C14	117.76 (14)	C35—C37—H37C	109.5
C16—C15—C14	122.16 (13)	H37A—C37—H37C	109.5
C17—C16—C15	119.60 (14)	H37B—C37—H37C	109.5
C17—C16—H16	120.2

C5—O5—C1—O1	−179.08 (11)	C2—O2—C14—O8	−6.7 (2)
C5—O5—C1—C2	−64.51 (15)	C2—O2—C14—C15	173.67 (12)
C7—O1—C1—O5	−68.08 (14)	O8—C14—C15—C20	8.7 (2)
C7—O1—C1—C2	175.85 (11)	O2—C14—C15—C20	−171.64 (13)
C14—O2—C2—C1	130.92 (13)	O8—C14—C15—C16	−171.60 (16)
C14—O2—C2—C3	−110.01 (14)	O2—C14—C15—C16	8.1 (2)
O5—C1—C2—O2	175.05 (11)	C20—C15—C16—C17	−0.6 (2)
O1—C1—C2—O2	−71.18 (13)	C14—C15—C16—C17	179.73 (14)
O5—C1—C2—C3	57.80 (14)	C15—C16—C17—C18	1.6 (2)
O1—C1—C2—C3	171.57 (11)	C16—C17—C18—C19	−1.2 (2)
O2—C2—C3—O3	67.38 (14)	C17—C18—C19—C20	−0.2 (2)
C1—C2—C3—O3	−174.82 (11)	C16—C15—C20—C19	−0.8 (2)
O2—C2—C3—C4	−171.01 (11)	C14—C15—C20—C19	178.91 (14)
C1—C2—C3—C4	−53.21 (15)	C18—C19—C20—C15	1.2 (2)
C21—O4—C4—C3	126.65 (13)	C4—O4—C21—O9	6.4 (2)
C21—O4—C4—C5	−114.68 (14)	C4—O4—C21—C22	−173.81 (12)
O3—C3—C4—O4	−69.61 (14)	O9—C21—C22—C23	171.75 (16)
C2—C3—C4—O4	170.31 (11)	O4—C21—C22—C23	−8.1 (2)
O3—C3—C4—C5	173.28 (11)	O9—C21—C22—C27	−8.3 (2)
C2—C3—C4—C5	53.19 (15)	O4—C21—C22—C27	171.87 (13)
C1—O5—C5—C6	−173.65 (12)	C27—C22—C23—C24	0.3 (2)
C1—O5—C5—C4	63.87 (15)	C21—C22—C23—C24	−179.82 (15)
O4—C4—C5—O5	−172.82 (10)	C22—C23—C24—C25	−1.1 (3)
C3—C4—C5—O5	−57.04 (14)	C23—C24—C25—C26	0.9 (3)
O4—C4—C5—C6	69.46 (15)	C24—C25—C26—C27	0.2 (3)
C3—C4—C5—C6	−174.76 (12)	C25—C26—C27—C22	−1.0 (2)
C28—O6—C6—C5	166.40 (13)	C23—C22—C27—C26	0.8 (2)
O5—C5—C6—O6	−56.43 (15)	C21—C22—C27—C26	−179.12 (14)
C4—C5—C6—O6	62.59 (16)	C6—O6—C28—O10	6.6 (2)
C1—O1—C7—O7	−4.90 (19)	C6—O6—C28—C29	−174.32 (13)
C1—O1—C7—C8	173.92 (11)	O10—C28—C29—C34	−6.8 (2)
O7—C7—C8—C9	0.6 (2)	O6—C28—C29—C34	174.10 (14)
O1—C7—C8—C9	−178.22 (14)	O10—C28—C29—C30	172.22 (16)
O7—C7—C8—C13	179.42 (15)	O6—C28—C29—C30	−6.9 (2)
O1—C7—C8—C13	0.6 (2)	C34—C29—C30—C31	1.5 (2)
C13—C8—C9—C10	0.6 (3)	C28—C29—C30—C31	−177.49 (15)
C7—C8—C9—C10	179.42 (17)	C29—C30—C31—C32	−1.0 (3)
C8—C9—C10—C11	−0.1 (3)	C30—C31—C32—C33	−0.2 (3)
C9—C10—C11—C12	−0.3 (3)	C31—C32—C33—C34	1.0 (3)
C10—C11—C12—C13	0.2 (3)	C32—C33—C34—C29	−0.5 (3)
C11—C12—C13—C8	0.3 (3)	C30—C29—C34—C33	−0.8 (2)
C9—C8—C13—C12	−0.7 (2)	C28—C29—C34—C33	178.30 (15)
C7—C8—C13—C12	−179.46 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O11	0.84	1.96	2.780 (2)	164

Methyl β-D-glucopyranoside hemihydrate (V) top

Crystal data top

2C₇H₁₄O₆·H₂O	D_x = 1.465 Mg m⁻³
M_r = 406.38	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P4₁2₁2	Cell parameters from 9836 reflections
a = 7.3482 (3) Å	θ = 5.2–71.9°
c = 34.1260 (17) Å	µ = 1.14 mm⁻¹
V = 1842.67 (17) Å³	T = 120 K
Z = 4	Block, colorless
F(000) = 872	0.21 × 0.16 × 0.08 mm

Data collection top

Bruker APEXII diffractometer	1797 independent reflections
Radiation source: Incoatec micro-focus	1786 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	R_int = 0.034
combination of ω and φ–scans	θ_max = 71.8°, θ_min = 5.2°
Absorption correction: numerical (SADABS; Krause et al., 2015)	h = −8→9
T_min = 0.862, T_max = 0.979	k = −9→9
27800 measured reflections	l = −41→42

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.0441P)² + 0.3075P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
1797 reflections	Δρ_max = 0.21 e Å⁻³
144 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 642 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: 0.03 (3)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.71499 (14)	0.64312 (13)	0.41589 (3)	0.0148 (2)
O2	0.79300 (14)	0.97599 (14)	0.37803 (3)	0.0156 (2)
H2O	0.830 (3)	0.903 (3)	0.3610 (6)	0.039 (6)*
O3	0.49078 (14)	1.20829 (14)	0.36875 (3)	0.0163 (2)
H3O	0.426 (3)	1.301 (3)	0.3727 (6)	0.038 (6)*
O4	0.24036 (13)	1.20553 (14)	0.43537 (3)	0.0151 (2)
H4O	0.161 (3)	1.242 (3)	0.4196 (5)	0.021 (5)*
O5	0.43923 (13)	0.75034 (12)	0.43612 (3)	0.0131 (2)
O6	0.16468 (14)	0.71645 (16)	0.49750 (3)	0.0205 (2)
H6O	0.234 (3)	0.625 (4)	0.4923 (6)	0.041 (6)*
C1	0.62279 (18)	0.79966 (18)	0.42600 (4)	0.0126 (3)
H1	0.6839	0.8614	0.4486	0.015*
C2	0.61456 (19)	0.92624 (19)	0.39063 (4)	0.0125 (3)
H2	0.5490	0.8643	0.3687	0.015*
C3	0.51080 (19)	1.09652 (18)	0.40257 (4)	0.0128 (3)
H3	0.5821	1.1639	0.4229	0.015*
C4	0.32364 (18)	1.04683 (18)	0.41924 (4)	0.0124 (3)
H4	0.2453	0.9983	0.3977	0.015*
C5	0.33969 (19)	0.90353 (18)	0.45146 (4)	0.0128 (3)
H5	0.4057	0.9557	0.4745	0.015*
C6	0.15507 (19)	0.8322 (2)	0.46429 (4)	0.0160 (3)
H6A	0.0749	0.9366	0.4704	0.019*
H6B	0.0993	0.7644	0.4423	0.019*
C7	0.7541 (2)	0.52994 (19)	0.44928 (4)	0.0186 (3)
H7A	0.8212	0.4217	0.4407	0.028*
H7B	0.6398	0.4927	0.4617	0.028*
H7C	0.8279	0.5984	0.4681	0.028*
O1W	0.37693 (15)	1.37693 (15)	0.5000	0.0221 (3)
H1WA	0.322 (3)	1.327 (3)	0.5188 (5)	0.029 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0170 (5)	0.0121 (5)	0.0154 (4)	0.0039 (4)	0.0025 (4)	0.0015 (4)
O2	0.0133 (5)	0.0130 (5)	0.0203 (5)	−0.0014 (4)	0.0056 (4)	−0.0008 (4)
O3	0.0178 (5)	0.0135 (5)	0.0175 (5)	0.0037 (4)	0.0039 (4)	0.0048 (4)
O4	0.0161 (5)	0.0151 (5)	0.0141 (4)	0.0058 (4)	−0.0019 (4)	−0.0021 (4)
O5	0.0118 (5)	0.0122 (5)	0.0152 (4)	−0.0001 (3)	0.0022 (3)	−0.0003 (4)
O6	0.0207 (5)	0.0232 (5)	0.0176 (5)	0.0003 (4)	0.0041 (4)	0.0060 (4)
C1	0.0114 (6)	0.0120 (6)	0.0143 (6)	0.0006 (5)	0.0008 (5)	−0.0001 (5)
C2	0.0115 (6)	0.0121 (6)	0.0140 (6)	−0.0013 (5)	0.0013 (5)	0.0005 (5)
C3	0.0141 (6)	0.0118 (6)	0.0124 (5)	0.0001 (5)	0.0005 (5)	0.0005 (5)
C4	0.0133 (6)	0.0127 (6)	0.0113 (6)	0.0017 (5)	0.0002 (5)	−0.0008 (5)
C5	0.0132 (7)	0.0129 (6)	0.0124 (5)	0.0015 (5)	0.0004 (5)	−0.0010 (5)
C6	0.0143 (7)	0.0185 (7)	0.0151 (6)	−0.0006 (5)	0.0015 (5)	0.0021 (5)
C7	0.0196 (7)	0.0158 (7)	0.0203 (7)	0.0040 (5)	0.0033 (6)	0.0072 (5)
O1W	0.0254 (5)	0.0254 (5)	0.0153 (7)	−0.0094 (7)	0.0023 (4)	−0.0023 (4)

Geometric parameters (Å, º) top

O1—C1	1.3789 (16)	O3—H3O	0.84 (3)
O1—C7	1.4399 (16)	O4—H4O	0.84 (2)
O2—C2	1.4275 (16)	O6—H6O	0.86 (3)
O3—C3	1.4241 (15)	C1—H1	1.0000
O4—C4	1.4273 (15)	C2—H2	1.0000
O5—C1	1.4387 (16)	C3—H3	1.0000
O5—C5	1.4409 (16)	C4—H4	1.0000
O6—C6	1.4187 (16)	C5—H5	1.0000
C1—C2	1.5252 (17)	C6—H6A	0.9900
C2—C3	1.5209 (18)	C6—H6B	0.9900
C3—C4	1.5324 (18)	C7—H7A	0.9800
C4—C5	1.5269 (17)	C7—H7B	0.9800
C5—C6	1.5188 (19)	C7—H7C	0.9800
O2—H2O	0.83 (2)	O1W—H1WA	0.84 (2)

C1—O1—C7	112.44 (10)	C2—C1—H1	110.5
C1—O5—C5	111.49 (10)	O2—C2—H2	109.5
O1—C1—O5	108.09 (11)	C3—C2—H2	109.5
O1—C1—C2	109.27 (10)	C1—C2—H2	109.5
O5—C1—C2	107.84 (11)	O3—C3—H3	109.3
O2—C2—C3	109.30 (11)	C2—C3—H3	109.3
O2—C2—C1	110.99 (11)	C4—C3—H3	109.3
C3—C2—C1	108.03 (10)	O4—C4—H4	109.2
O3—C3—C2	108.00 (10)	C5—C4—H4	109.2
O3—C3—C4	110.22 (11)	C3—C4—H4	109.2
C2—C3—C4	110.69 (11)	O5—C5—H5	109.8
O4—C4—C5	108.60 (10)	C6—C5—H5	109.8
O4—C4—C3	109.47 (11)	C4—C5—H5	109.8
C5—C4—C3	111.25 (11)	O6—C6—H6A	109.0
O5—C5—C6	106.77 (10)	C5—C6—H6A	109.0
O5—C5—C4	108.44 (10)	O6—C6—H6B	109.0
C6—C5—C4	112.12 (11)	C5—C6—H6B	109.0
O6—C6—C5	113.12 (11)	H6A—C6—H6B	107.8
C2—O2—H2O	110.3 (17)	O1—C7—H7A	109.5
C3—O3—H3O	113.4 (15)	O1—C7—H7B	109.5
C4—O4—H4O	108.1 (13)	H7A—C7—H7B	109.5
C6—O6—H6O	109.4 (15)	O1—C7—H7C	109.5
O1—C1—H1	110.5	H7A—C7—H7C	109.5
O5—C1—H1	110.5	H7B—C7—H7C	109.5

C7—O1—C1—O5	−72.32 (13)	O3—C3—C4—O4	−68.92 (13)
C7—O1—C1—C2	170.57 (11)	C2—C3—C4—O4	171.66 (10)
C5—O5—C1—O1	173.23 (9)	O3—C3—C4—C5	171.06 (10)
C5—O5—C1—C2	−68.74 (12)	C2—C3—C4—C5	51.64 (14)
O1—C1—C2—O2	−60.70 (14)	C1—O5—C5—C6	−175.22 (10)
O5—C1—C2—O2	−177.97 (10)	C1—O5—C5—C4	63.78 (13)
O1—C1—C2—C3	179.49 (11)	O4—C4—C5—O5	−174.60 (10)
O5—C1—C2—C3	62.22 (13)	C3—C4—C5—O5	−54.06 (14)
O2—C2—C3—O3	63.60 (13)	O4—C4—C5—C6	67.77 (13)
C1—C2—C3—O3	−175.53 (11)	C3—C4—C5—C6	−171.70 (11)
O2—C2—C3—C4	−175.65 (10)	O5—C5—C6—O6	68.93 (13)
C1—C2—C3—C4	−54.79 (13)	C4—C5—C6—O6	−172.45 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O5ⁱ	0.83 (2)	2.12 (2)	2.952 (2)	172 (2)
O3—H3O···O2ⁱⁱ	0.84 (3)	1.91 (3)	2.740 (2)	169 (2)
O4—H4O···O3ⁱⁱ	0.84 (2)	1.85 (2)	2.679 (2)	172 (2)
O6—H6O···O1Wⁱⁱⁱ	0.86 (3)	2.12 (3)	2.944 (2)	160 (2)
O1W—H1WA···O4^iv	0.84 (2)	1.89 (2)	2.731 (2)	173 (2)

Symmetry codes: (i) x+1/2, −y+3/2, −z+3/4; (ii) x−1/2, −y+5/2, −z+3/4; (iii) x, y−1, z; (iv) y−1, x+1, −z+1.

Comparison of structural parameters in (I), (IIIa) and (IIIb) top

Parameter	(I)	(IIIa)	(IIIb)
Bond lengths and internuclear distances (Å)
C1—C2	1.516 (3)	1.498 (8)	1.522 (7)
C2—C3	1.519 (3)	1.524 (7)	1.510 (7)
C3—C4	1.531 (3)	1.529 (7)	1.532 (7)
C4—C5	1.530 (3)	1.531 (7)	1.524 (7)
C5—C6	1.508 (3)	1.509 (7)	1.493 (7)
C1'—C2'	1.527 (3)	1.522 (7)	1.522 (7)
C2'—C3'	1.531 (3)	1.508 (7)	1.521 (7)
C3'—C4'	1.521 (3)	1.503 (7)	1.508 (7)
C4'—C5'	1.521 (3)	1.524 (7)	1.524 (7)
C5'—C6'	1.511 (3)	1.494 (7)	1.506 (7)
C1—O1	1.384 (3)	1.437 (6)	1.413 (6)
C1—O5	1.413 (3)	1.398 (6)	1.414 (6)
C2—O2	1.418 (3)	1.442 (6)	1.440 (6)
C3—O3	1.421 (3)	1.413 (6)	1.434 (6)
C4—O4
C5—O5	1.428 (3)	1.440 (6)	1.441 (6)
C6—O6	1.424 (3)	1.447 (6)	1.453 (6)
C1'—O1'	1.387 (3)	1.376 (6)	1.389 (6)
C1'—O5'	1.425 (3)	1.442 (6)	1.430 (6)
C2'—O2'	1.414 (3)	1.429 (6)	1.440 (6)
C3'—O3'	1.422 (3)	1.438 (6)	1.441 (6)
C4'—O4'	1.423 (3)	1.451 (6)	1.443 (6)
C5'—O5'	1.432 (3)	1.438 (6)	1.437 (6)
C6'—O6'	1.426 (3)	1.451 (6)	1.450 (6)
C4—O1'	1.437 (3)	1.435 (6)	1.433 (6)
O1—CH₃	1.420 (4)
O1—CO		1.369 (7)	1.374 (6)
O3···O5'	2.764 (2)	2.797 (5)	2.806 (5)

Bond angles (°)
C1'—O1'—C4	116.22 (2)	116.97 (4)	117.92 (4)
C1—O1—CH₃	113.71 (2)
C1—O1—CO		116.27 (4)	115.48 (4)

Torsion angles (°)
C2—C1—O1—CH₃ (φ)	164.23 (2)
C2—C1—O1—CO (φ)		102.31 (5)	108.33 (5)
O5—C1—O1—CH₃ (φ)	-77.35 (3)
O5—C1—O1—CO (φ)		-139.21 (4)	-133.65 (4)
C2—C3—O3—H	-158.98	-134.24	-152.22
C1—C2—C3—C4	-44.22	-53.61 (5)	-53.42 (5)
C1'—C2'—C3'—C4'	-54.82	-52.55 (6)	-54.48 (6)
C1—O5—C5—C4	67.57	63.33 (5)	65.96 (5)
C1'—O5'—C5'—C4'	64.96	64.28 (5)	63.71 (5)
C2'—C1'—O1'—C4 (φ')	153.78 (2)	151.47 (4)	150.66 (4)
O5'—C1'—O1'—C4 (φ')	-88.44 (2)	-90.91 (5)	-91.97 (5)
C1'—O1'—C4—C3 (ψ')	78.42 (2)	64.87 (5)	66.00 (5)
C1'—O1'—C4—C5 (ψ')	-161.30 (2)	-174.84 (4)	-174.87 (4)
H1'—C1'—O1'—C4 (φ')	31.92	30.01	29.33
C1'—O1'—C4—H4 (ψ')	-43.65	-57.83	-57.32
O5—C5—C6—O6 (ω)	-4.60 (gg)	-65.78 (5) (gg)	-66.29 (5) (gg)
O5'—C5'—C6'—O6' (ω')	57.26 (gt)	67.75 (5) (gt)	68.60 (5) (gt)

Note: gg is gauche–gauche and gt gauche–trans.

Comparison of structural parameters in (IV and (V) top

Parameter	Compound
	(IV)	(V)
Bond lengths and internuclear distances (Å)
C1—C2	1.517 (2)	1.525 (2)
C2—C3	1.524 (2)	1.521 (2)
C3—C4	1.524 (2)	1.532 (2)
C4—C5	1.526 (2)	1.527 (2)
C5—C6	1.509 (2)	1.519 (2)
C1—O1	1.420 (2)	1.379 (2)
C1—O5	1.411 (2)	1.439 (2)
C2—O2	1.441 (2)	1.428 (2)
C3—O3	1.416 (2)	1.424 (2)
C4—O4	1.449 (2)	1.427 (2)
C5—O5	1.427 (2)	1.441 (2)
C6—O6	1.440 (2)	1.419 (2)
O1—CH₃		1.440 (2)
O1—CO	1.359 (2)

Bond angles (°)
C1—O1—CH₃		112.44 (10)
C1—O1—CO	115.31 (11)

Torsion angles (°)
C2—C1—O1—CH₃		170.57 (11)
C2—C1—O1—CO	175.85 (11)
O5—C1—O1—CH₃		-72.32 (13)
O5—C1—O1—CO	-68.08 (14)
C2—C3—O3—H	-144.61	174.71
C1—C2—C3—C4	-53.21 (15)	-54.79 (13)
C1—O5—C5—C4	63.87 (15)	63.78 (13)
O5—C5—C6—O6 (ω)	-56.43 (15) (gg)	68.93 (13) (gt)

Note: gg is gauche–gauche and gt gauche–trans.

Cremer–Pople puckering parameters for aldopyranosyl residues in (I), (IIIa), (IIIb), (IV) and (V) top

Compound/residue	θ (°)	φ (°)	Q (Å)	q₂ (Å)	q₃ (Å)
(I): βGalp	4.7	28.2	0.5948	0.0485	0.5928
(I): βGlcp	12.0	341.5	0.5579	0.1159	0.5457
(IIIa): βGalp	5.0 (5)	347 (6)	0.575 (5)	0.053 (5)	0.573 (5)
(IIIa): βGlcp	7.8 (5)	38 (4)	0.595 (5)	0.080 (5)	0.590 (5)
(IIIb): βGalp	2.7 (5)	311 (9)	0.583 (5)	0.030 (5)	0.583 (5)
(IIIb): βGlcp	6.9 (5)	18 (4)	0.607 (5)	0.071 (5)	0.603 (5)
(IV): βGlcp	3.4 (2)	1(3)	0.585 (2)	0.035 (2)	0.584 (2)
(V): βGlcp	7.5 (1)	41.9 (1)	0.604 (1)	0.079 (1)	0.599 (1)

Characterization of O-benzoyl ester side-chain conformations in (III) and (IV) using internuclear distances r₁ and r₂ (Fig. 4). top

			Internuclear distance (Å)
Substitution site
	r₁ (IIIa)	r₁ (IIIb)	r₁ (IV)	r₂ (IIIa)	r₂ (IIIb)	r₂ (IV)
C1	2.253	2.205	2.537	2.535	2.549	2.512
C2	2.286	2.381	2.271	2.558	2.596	2.538
C4			2.333			2.569
C6^b	2.439	2.445	2.518	2.503	2.507	2.565
	2.653	2.693	2.771
C2'	2.325	2.330		2.601	2.611
C3'	2.187	2.178		2.553	2.533
C4'	2.252	2.271		2.521	2.517
C6'^b	2.601	2.597		2.528	2.547
	2.604	2.575
Avg±SD^a	2.261 ± 0.051^c	2.273 ± 0.085^c	2.380 ± 0.139^c	2.543 ± 0.032	2.551 ± 0.039	2.546 ± 0.027
	2.574 ± 0.093^d	2.578 ± 0.102^d	2.645 ± 0.179^d

Notes: (a) SD = standard deviation; (b) the two values of r₁ shown are the internuclear distances between the ester carbonyl O atom and the two diastereotopic H atoms on C6 (H6R and H6S). (c) For 2°-OH benzoates. (d) For 1°-OH benzoates. See Fig. 4 for definitions of r₁ and r₂.

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O-Benzoyl side-chain conformations in 2,3,4,6-tetra-O-benzoyl-β-D-galacto­pyranosyl-(1→4)-1,2,6-tri-O-benzoyl-β-D-gluco­pyran­ose (ethyl acetate solvate) and 1,2,4,6-tetra-O-benzoyl-β-D-gluco­pyran­ose (acetone solvate)

Supporting information

O-Benzoyl side-chain conformations in 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→4)-1,2,6-tri-O-benzoyl-β-D-glucopyranose (ethyl acetate solvate) and 1,2,4,6-tetra-O-benzoyl-β-D-glucopyranose (acetone solvate)