Inclusion complex of β-cyclo­dextrin with coffee chloro­genic acid: new insights from a combined crystallographic and theoretical study

This work reports the elusive structural evidence for the [4]pseudorotaxane of β-cyclo­dextrin (β-CD) with coffee chloro­genic acid (CGA), a conjugate of caffeic acid (CFA) and quinic acid (QNA). A single-crystal X-ray structure analysis of the inclusion complex β-cyclo­dextrin–chloro­genic acid–water (2/2/17), 2C₄₂H₇₀O₃₅·2C₁₆H₁₈O₉·17H₂O, reveals that CGA threads through β-CD and assembles via O—H...O hydrogen bonds and parallel-displaced π–π inter­actions in the twofold symmetry-related dimer yielding a [4]pseudorotaxane, which is crystallographically observed for the first time in CD inclusion complexes. The encapsulation of the aromatic ring and C=C—C(=O)O chain in the β-CD dimeric cavity indicates that the CFA moiety plays a determinant role in complexation. This is in agreement with the DFT-derived relative thermodynamic stabilities of the trimodal β-CD–CGA inclusion complexes, that is, β-CD complexed with different CGA components: C=C—C(=O)O chain > cyclo­hexane ring > aromatic ring. The complexation stability is further enhanced in the dimeric β-CD–CGA complex, with the CFA moiety totally enclosed in the β-CD dimeric cavity.

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: XT in SHELXL2014 (Sheldrick, 2015); program(s) used to refine structure: XLMP in SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: XPREP (Bruker, 2008) and SHELXTL (Bruker, 2014).

β-Cyclodextrin–chlorogenic acid–water (2/2/17)

Crystal data

2C42H70O35·2C16H18O9·17H2O	Dx = 1.520 Mg m^−3
Mr = 3267.51	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, C2221	Cell parameters from 7058 reflections
a = 19.0698 (3) Å	θ = 2.4–21.6°
b = 24.1017 (5) Å	µ = 0.14 mm^−1
c = 31.0577 (4) Å	T = 100 K
V = 14274.6 (4) Å^3	Plate, colorless
Z = 4	0.26 × 0.14 × 0.06 mm
F(000) = 6915

Data collection

Bruker APEXII KappaCCD diffractometer	13217 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.076
ω–φ scan	θmax = 30.8°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −27→25
Tmin = 0.669, Tmax = 0.746	k = −34→34
67302 measured reflections	l = −43→44
21982 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.069	w = 1/[σ^2(Fo^2) + (0.0976P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.196	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 0.83 e Å^−3
21982 reflections	Δρmin = −0.75 e Å^−3
1049 parameters	Absolute structure: Flack x determined using 4198 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
29 restraints	Absolute structure parameter: 0.1 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C11	0.1627 (2)	0.2090 (2)	0.35291 (15)	0.0217 (10)
H11	0.1243	0.1811	0.3564	0.026*
C21	0.1492 (3)	0.2435 (2)	0.31234 (15)	0.0242 (10)
H21	0.1037	0.2635	0.3163	0.029*
C31	0.2069 (3)	0.2867 (2)	0.30777 (14)	0.0214 (10)
H31	0.2532	0.2678	0.3042	0.026*
C41	0.2080 (2)	0.32195 (19)	0.34786 (14)	0.0193 (9)
H41	0.1628	0.3428	0.3501	0.023*
C51	0.2179 (3)	0.2867 (2)	0.38794 (14)	0.0203 (9)
H51	0.2653	0.2691	0.3870	0.024*
C61	0.2107 (3)	0.3198 (2)	0.42985 (15)	0.0268 (11)
H611	0.2128	0.2939	0.4546	0.032*
H621	0.2507	0.3458	0.4323	0.032*
O21	0.1434 (2)	0.21001 (17)	0.27506 (12)	0.0320 (9)
H21O	0.1753	0.1860	0.2751	0.048*
O31	0.1934 (2)	0.32133 (15)	0.27093 (11)	0.0262 (8)
H31O	0.2242	0.3462	0.2694	0.039*
O41	0.26395 (17)	0.36017 (13)	0.34431 (10)	0.0202 (7)
O51	0.16530 (18)	0.24372 (14)	0.38994 (10)	0.0227 (7)
O61	0.1474 (2)	0.35014 (15)	0.43183 (12)	0.0296 (8)
H61O	0.1158	0.3301	0.4425	0.044*
C12	0.2494 (3)	0.41727 (19)	0.34909 (14)	0.0196 (9)
H12	0.1975	0.4228	0.3470	0.024*
C22	0.2844 (3)	0.4483 (2)	0.31191 (14)	0.0192 (9)
H22	0.2733	0.4887	0.3147	0.023*
C32	0.3620 (2)	0.4411 (2)	0.31502 (14)	0.0196 (9)
H32	0.3741	0.4009	0.3118	0.024*
C42	0.3857 (2)	0.4614 (2)	0.35872 (14)	0.0202 (9)
H42	0.3781	0.5024	0.3609	0.024*
C52	0.3467 (2)	0.4322 (2)	0.39503 (14)	0.0205 (9)
H52	0.3594	0.3920	0.3950	0.025*
C62	0.3622 (3)	0.4567 (2)	0.43919 (15)	0.0263 (11)
H612	0.3322	0.4383	0.4610	0.032*
H622	0.4117	0.4493	0.4468	0.032*
O22	0.25744 (18)	0.42883 (15)	0.27168 (10)	0.0243 (7)
H22O	0.2226	0.4481	0.2645	0.036*
O32	0.39369 (19)	0.47216 (15)	0.28092 (10)	0.0261 (8)
H32O	0.3738	0.5031	0.2787	0.039*
O42	0.45879 (17)	0.44934 (14)	0.36330 (10)	0.0207 (7)
O52	0.27248 (17)	0.43788 (14)	0.38885 (10)	0.0210 (7)
O62	0.3498 (2)	0.51476 (15)	0.44016 (11)	0.0322 (9)
H62O	0.3429	0.5263	0.4150	0.048*
C13	0.5037 (3)	0.4936 (2)	0.37491 (15)	0.0219 (10)
H13	0.4755	0.5283	0.3782	0.026*
C23	0.5572 (3)	0.5015 (2)	0.33881 (15)	0.0249 (10)
H23	0.5896	0.5327	0.3461	0.030*
C33	0.5986 (3)	0.4484 (2)	0.33407 (14)	0.0215 (10)
H33	0.5662	0.4171	0.3266	0.026*
C43	0.6343 (3)	0.4366 (2)	0.37675 (14)	0.0187 (9)
H43	0.6685	0.4669	0.3831	0.022*
C53	0.5810 (2)	0.4330 (2)	0.41345 (15)	0.0206 (9)
H53	0.5507	0.3995	0.4092	0.025*
C63	0.6149 (3)	0.4302 (2)	0.45707 (15)	0.0227 (10)
H613	0.5785	0.4329	0.4796	0.027*
H623	0.6390	0.3940	0.4604	0.027*
O23	0.5217 (2)	0.51315 (18)	0.29953 (12)	0.0352 (10)
H23O	0.5442	0.5372	0.2856	0.053*
O33	0.65148 (18)	0.45321 (17)	0.30220 (10)	0.0285 (8)
H33O	0.6328	0.4563	0.2778	0.043*
O43	0.67102 (18)	0.38508 (14)	0.37340 (10)	0.0208 (7)
O53	0.53795 (18)	0.48162 (14)	0.41414 (11)	0.0237 (7)
O63	0.66423 (19)	0.47378 (15)	0.46248 (11)	0.0243 (7)
H63O	0.7045	0.4622	0.4563	0.036*
C14	0.7413 (3)	0.38445 (19)	0.38642 (14)	0.0207 (10)
H14	0.7562	0.4235	0.3921	0.025*
C24	0.7863 (3)	0.3614 (2)	0.35030 (16)	0.0230 (10)
H24	0.8364	0.3638	0.3595	0.028*
C34	0.7692 (3)	0.3006 (2)	0.34259 (14)	0.0227 (10)
H34	0.7196	0.2973	0.3325	0.027*
C44	0.7776 (3)	0.26940 (19)	0.38441 (15)	0.0211 (10)
H44	0.8281	0.2688	0.3930	0.025*
C54	0.7341 (3)	0.2952 (2)	0.42005 (15)	0.0211 (9)
H54	0.6834	0.2916	0.4123	0.025*
C64	0.7453 (3)	0.2695 (2)	0.46393 (15)	0.0251 (10)
H614	0.7174	0.2904	0.4854	0.030*
H624	0.7275	0.2310	0.4635	0.030*
O24	0.7783 (2)	0.39404 (15)	0.31218 (11)	0.0256 (7)
H24O	0.8169	0.3960	0.2993	0.038*
O34	0.8150 (2)	0.27741 (16)	0.31086 (11)	0.0320 (9)
H34O	0.8059	0.2913	0.2867	0.048*
O44	0.75330 (18)	0.21389 (14)	0.37741 (11)	0.0234 (7)
O54	0.75062 (18)	0.35335 (14)	0.42452 (10)	0.0228 (7)
O64	0.8157 (2)	0.26889 (17)	0.47719 (11)	0.0318 (9)
H64O	0.8303	0.3016	0.4797	0.048*
C15	0.7987 (3)	0.1688 (2)	0.38732 (15)	0.0225 (10)
H15	0.8470	0.1831	0.3934	0.027*
C25	0.8001 (3)	0.1318 (2)	0.34759 (15)	0.0226 (10)
H25	0.8301	0.0986	0.3536	0.027*
C35	0.7271 (3)	0.1129 (2)	0.33787 (15)	0.0237 (10)
H35	0.6974	0.1460	0.3311	0.028*
C45	0.6975 (3)	0.0837 (2)	0.37740 (15)	0.0218 (10)
H45	0.7224	0.0477	0.3820	0.026*
C55	0.7031 (3)	0.1195 (2)	0.41773 (16)	0.0241 (10)
H55	0.6716	0.1524	0.4143	0.029*
C65	0.6829 (3)	0.0890 (2)	0.45930 (16)	0.0289 (11)
H615	0.6966	0.1120	0.4843	0.035*
H625	0.6314	0.0843	0.4601	0.035*
O25	0.8294 (2)	0.16176 (16)	0.31217 (11)	0.0305 (8)
H25O	0.8485	0.1394	0.2950	0.046*
O35	0.7272 (2)	0.07659 (14)	0.30173 (11)	0.0264 (8)
H35O	0.6948	0.0532	0.3044	0.040*
O45	0.62530 (18)	0.07361 (14)	0.36713 (11)	0.0224 (7)
O55	0.77363 (19)	0.13886 (15)	0.42321 (11)	0.0249 (7)
O65	0.7154 (2)	0.03594 (16)	0.46284 (12)	0.0354 (9)
H65O	0.7504	0.0346	0.4464	0.053*
C16	0.5967 (3)	0.0212 (2)	0.37782 (16)	0.0238 (10)
H16	0.6357	−0.0036	0.3876	0.029*
C26	0.5633 (3)	−0.0042 (2)	0.33764 (15)	0.0229 (10)
H26	0.5516	−0.0438	0.3439	0.027*
C36	0.4962 (3)	0.02572 (19)	0.32513 (15)	0.0208 (10)
H36	0.5080	0.0644	0.3159	0.025*
C46	0.4485 (3)	0.0283 (2)	0.36429 (15)	0.0208 (9)
H46	0.4361	−0.0101	0.3739	0.025*
C56	0.4872 (3)	0.0588 (2)	0.40027 (15)	0.0232 (10)
H56	0.5031	0.0958	0.3893	0.028*
C66	0.4472 (3)	0.0670 (2)	0.44190 (15)	0.0256 (10)
H616	0.4001	0.0821	0.4355	0.031*
H626	0.4412	0.0307	0.4565	0.031*
O26	0.61300 (19)	−0.00284 (16)	0.30375 (11)	0.0275 (8)
H26O	0.6115	−0.0329	0.2900	0.041*
O36	0.4641 (2)	−0.00235 (16)	0.29044 (11)	0.0279 (8)
H36O	0.4416	−0.0298	0.2998	0.042*
O46	0.38654 (17)	0.05748 (13)	0.35199 (11)	0.0207 (7)
O56	0.54778 (19)	0.02612 (14)	0.41145 (11)	0.0245 (7)
O66	0.48358 (19)	0.10397 (16)	0.46958 (11)	0.0285 (8)
H66O	0.4545	0.1226	0.4839	0.043*
C17	0.3222 (3)	0.0291 (2)	0.35555 (16)	0.0235 (10)
H17	0.3317	−0.0115	0.3584	0.028*
C27	0.2804 (3)	0.0392 (2)	0.31492 (16)	0.0255 (11)
H27	0.2347	0.0192	0.3175	0.031*
C37	0.2655 (3)	0.1008 (2)	0.31011 (15)	0.0246 (10)
H37	0.3107	0.1212	0.3062	0.030*
C47	0.2289 (3)	0.12180 (19)	0.35060 (15)	0.0203 (9)
H47	0.1799	0.1071	0.3516	0.024*
C57	0.2671 (3)	0.1060 (2)	0.39147 (15)	0.0213 (10)
H57	0.3117	0.1276	0.3933	0.026*
C67	0.2247 (3)	0.1160 (2)	0.43198 (16)	0.0297 (12)
H617	0.2508	0.1013	0.4570	0.036*
H627	0.2188	0.1564	0.4362	0.036*
O27	0.3168 (2)	0.01828 (15)	0.27777 (12)	0.0298 (8)
H27O	0.3559	0.0341	0.2756	0.045*
O37	0.2208 (2)	0.11152 (16)	0.27432 (11)	0.0306 (8)
H37O	0.1851	0.0911	0.2759	0.046*
O47	0.22734 (18)	0.18113 (13)	0.34719 (10)	0.0210 (7)
O57	0.28354 (19)	0.04713 (15)	0.39172 (11)	0.0246 (7)
O67	0.1575 (2)	0.09052 (17)	0.43024 (13)	0.0366 (10)
H67O	0.1597	0.0586	0.4411	0.055*
C1'	0.4041 (3)	0.2235 (3)	0.26958 (17)	0.0360 (14)
C2'	0.3958 (4)	0.2769 (3)	0.25393 (19)	0.0464 (17)
H2'	0.3864	0.3073	0.2726	0.056*
C3'	0.4018 (4)	0.2839 (3)	0.2110 (2)	0.061 (2)
H3B	0.3980	0.3210	0.2009	0.074*	0.516 (7)
O1'A	0.4000 (5)	0.3368 (3)	0.1970 (3)	0.0424 (15)	0.484 (7)
H1A	0.3593	0.3444	0.1885	0.064*	0.484 (7)
C4'	0.4122 (3)	0.2464 (5)	0.18162 (19)	0.059 (2)
O2'	0.4164 (2)	0.2607 (3)	0.13860 (13)	0.0591 (15)
H2'O	0.4260	0.2324	0.1240	0.089*
C5'	0.4203 (3)	0.1927 (4)	0.1967 (2)	0.061 (3)
H5A	0.4292	0.1635	0.1769	0.073*	0.484 (7)
O1'B	0.4445 (4)	0.1650 (3)	0.1620 (2)	0.0424 (15)	0.516 (7)
H1B	0.4156	0.1403	0.1550	0.064*	0.516 (7)
C6'	0.4159 (3)	0.1809 (3)	0.23952 (19)	0.0455 (17)
H6'	0.4207	0.1437	0.2491	0.055*
C7'	0.4063 (3)	0.2112 (3)	0.31520 (17)	0.0318 (12)
H7'	0.4054	0.1732	0.3232	0.038*
C8'	0.4096 (3)	0.2487 (2)	0.34733 (16)	0.0274 (11)
H8'	0.4063	0.2871	0.3407	0.033*
C9'	0.4182 (3)	0.2313 (2)	0.39233 (17)	0.0265 (11)
O3'	0.4099 (2)	0.18526 (16)	0.40688 (12)	0.0323 (9)
C1	0.4662 (3)	0.3179 (2)	0.53101 (15)	0.0219 (10)
O1	0.43341 (18)	0.27424 (14)	0.55525 (11)	0.0235 (7)
H1O	0.3953	0.2655	0.5435	0.035*
C2	0.5454 (3)	0.3065 (2)	0.53260 (16)	0.0246 (10)
H21E	0.5709	0.3380	0.5195	0.030*
H22E	0.5606	0.3031	0.5630	0.030*
C3	0.5630 (3)	0.2533 (2)	0.50839 (15)	0.0246 (10)
H3	0.6153	0.2508	0.5071	0.030*
O2	0.53901 (19)	0.20479 (15)	0.53014 (12)	0.0283 (8)
H2O	0.5019	0.2121	0.5436	0.042*
C4	0.5368 (3)	0.2548 (2)	0.46210 (16)	0.0231 (10)
H4	0.5604	0.2869	0.4477	0.028*
O3	0.55639 (19)	0.20613 (15)	0.43885 (12)	0.0274 (8)
H3O	0.5298	0.1798	0.4458	0.041*
C5	0.4591 (3)	0.2659 (2)	0.46057 (15)	0.0213 (10)
H5	0.4327	0.2336	0.4727	0.026*
O4	0.43831 (18)	0.27572 (14)	0.41637 (10)	0.0235 (7)
C6	0.4403 (3)	0.3186 (2)	0.48470 (14)	0.0210 (9)
H61	0.3887	0.3232	0.4846	0.025*
H62	0.4610	0.3508	0.4696	0.025*
C7	0.4518 (3)	0.3732 (2)	0.55358 (16)	0.0276 (11)
O5	0.4502 (2)	0.37644 (17)	0.59379 (11)	0.0372 (10)
O6	0.4394 (2)	0.41420 (16)	0.52895 (12)	0.0397 (10)
H6O	0.4309	0.4424	0.5439	0.060*
O1W	0.4676 (10)	0.1675 (8)	0.6085 (5)	0.058 (5)	0.3
O2W	0.4589 (4)	0.1155 (4)	0.5953 (2)	0.069 (2)	0.7
O3W	0.4881 (6)	0.2853 (5)	0.6420 (3)	0.084 (3)*	0.6
O4W	0.4974 (11)	0.3312 (8)	0.6655 (6)	0.098 (6)*	0.4
O5W	0.5036 (15)	0.6305 (12)	0.3003 (9)	0.108 (8)*	0.3
O6W	0.5694 (7)	0.6024 (6)	0.2688 (4)	0.077 (3)*	0.5
O7W	0.5988 (8)	0.5909 (6)	0.2353 (5)	0.088 (4)*	0.5
O8W	0.8059 (2)	0.46211 (19)	0.46626 (14)	0.0477 (12)
H1W8	0.8162	0.4859	0.4423	0.072*
H2W8	0.8474	0.4623	0.4834	0.072*
O9W	0.8845 (3)	0.3646 (2)	0.47283 (18)	0.0629 (16)
H1W9	0.9223	0.3669	0.4525	0.094*
H2W9	0.8461	0.3831	0.4591	0.094*
O10A	0.5891 (4)	−0.1006 (3)	0.2665 (3)	0.0545 (17)	0.8
O10B	0.5982 (16)	−0.0939 (10)	0.2388 (9)	0.048 (7)	0.2
O11W	0.4755 (5)	0.1366 (4)	0.6866 (3)	0.047 (2)	0.5
H111	0.4765	0.1705	0.6712	0.071*	0.5
H211	0.4332	0.1378	0.7035	0.071*	0.5
O12W	0.4611 (4)	0.2455 (4)	0.7155 (3)	0.090 (3)	0.7
H112	0.4205	0.2362	0.6987	0.135*	0.7
H212	0.4438	0.2626	0.7409	0.135*	0.7
O13W	0.5658 (3)	0.0650 (2)	0.53389 (16)	0.0619 (15)
H113	0.5260	0.0686	0.5151	0.093*
H213	0.5620	0.0281	0.5454	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.021 (2)	0.021 (2)	0.023 (2)	0.0010 (19)	0.002 (2)	0.0001 (19)
C21	0.022 (2)	0.030 (3)	0.021 (2)	0.001 (2)	−0.004 (2)	−0.003 (2)
C31	0.026 (2)	0.022 (2)	0.017 (2)	0.0041 (19)	0.0000 (19)	0.0030 (18)
C41	0.019 (2)	0.022 (2)	0.017 (2)	−0.0009 (18)	−0.0004 (19)	−0.0005 (18)
C51	0.022 (2)	0.020 (2)	0.018 (2)	−0.0010 (19)	0.0022 (19)	0.0018 (18)
C61	0.040 (3)	0.023 (3)	0.018 (2)	−0.008 (2)	0.003 (2)	0.0025 (19)
O21	0.035 (2)	0.033 (2)	0.0285 (19)	0.0062 (17)	−0.0050 (17)	−0.0100 (16)
O31	0.039 (2)	0.0207 (18)	0.0194 (16)	0.0000 (16)	−0.0032 (16)	0.0005 (14)
O41	0.0215 (17)	0.0164 (16)	0.0227 (16)	0.0020 (13)	0.0021 (14)	0.0019 (13)
O51	0.0271 (18)	0.0211 (17)	0.0199 (15)	−0.0041 (14)	0.0058 (14)	−0.0024 (14)
O61	0.034 (2)	0.0221 (18)	0.033 (2)	−0.0050 (16)	0.0130 (17)	−0.0049 (15)
C12	0.022 (2)	0.019 (2)	0.018 (2)	0.0051 (18)	0.0017 (19)	−0.0029 (17)
C22	0.023 (2)	0.020 (2)	0.015 (2)	0.0004 (18)	−0.0014 (18)	−0.0004 (17)
C32	0.020 (2)	0.022 (2)	0.016 (2)	−0.0003 (18)	0.0009 (18)	0.0022 (18)
C42	0.019 (2)	0.023 (2)	0.018 (2)	0.0046 (18)	0.0010 (18)	−0.0019 (18)
C52	0.021 (2)	0.024 (2)	0.016 (2)	0.0025 (19)	0.0018 (18)	−0.0006 (18)
C62	0.030 (3)	0.034 (3)	0.016 (2)	−0.003 (2)	0.000 (2)	0.001 (2)
O22	0.0244 (18)	0.0277 (18)	0.0207 (16)	0.0003 (15)	−0.0040 (15)	0.0001 (14)
O32	0.0298 (19)	0.0299 (19)	0.0186 (16)	−0.0026 (16)	0.0022 (15)	0.0036 (14)
O42	0.0179 (16)	0.0199 (16)	0.0245 (16)	0.0030 (13)	−0.0024 (14)	−0.0039 (13)
O52	0.0204 (16)	0.0264 (18)	0.0161 (15)	0.0014 (14)	0.0006 (14)	−0.0027 (13)
O62	0.049 (2)	0.027 (2)	0.0210 (17)	−0.0066 (17)	0.0019 (17)	−0.0035 (15)
C13	0.023 (2)	0.020 (2)	0.023 (2)	0.0040 (19)	−0.001 (2)	−0.0017 (19)
C23	0.024 (2)	0.027 (3)	0.023 (2)	−0.001 (2)	−0.003 (2)	0.004 (2)
C33	0.020 (2)	0.028 (3)	0.016 (2)	−0.0016 (19)	−0.0022 (18)	0.0019 (19)
C43	0.023 (2)	0.018 (2)	0.015 (2)	0.0008 (18)	−0.0004 (18)	−0.0016 (17)
C53	0.022 (2)	0.020 (2)	0.020 (2)	0.0026 (18)	−0.0022 (19)	−0.0012 (18)
C63	0.023 (2)	0.026 (2)	0.019 (2)	0.002 (2)	0.0015 (19)	−0.0007 (19)
O23	0.027 (2)	0.052 (3)	0.0268 (19)	−0.0028 (18)	−0.0048 (16)	0.0173 (18)
O33	0.0239 (18)	0.048 (2)	0.0138 (15)	0.0005 (17)	0.0001 (14)	0.0012 (16)
O43	0.0249 (18)	0.0182 (16)	0.0194 (15)	−0.0014 (13)	−0.0025 (14)	−0.0024 (13)
O53	0.0243 (17)	0.0251 (18)	0.0216 (16)	0.0057 (14)	−0.0037 (14)	−0.0055 (14)
O63	0.0238 (18)	0.0307 (19)	0.0184 (16)	−0.0001 (15)	0.0000 (15)	−0.0031 (14)
C14	0.028 (3)	0.017 (2)	0.017 (2)	−0.0011 (19)	−0.0015 (19)	0.0013 (17)
C24	0.024 (2)	0.021 (2)	0.024 (2)	0.0015 (19)	0.001 (2)	0.0018 (19)
C34	0.030 (3)	0.023 (2)	0.015 (2)	0.002 (2)	−0.004 (2)	−0.0009 (17)
C44	0.025 (2)	0.018 (2)	0.020 (2)	0.0020 (19)	0.000 (2)	−0.0003 (17)
C54	0.020 (2)	0.020 (2)	0.023 (2)	0.0016 (18)	−0.0043 (19)	0.0000 (18)
C64	0.025 (2)	0.032 (3)	0.018 (2)	0.004 (2)	0.005 (2)	0.0022 (19)
O24	0.0297 (19)	0.0253 (18)	0.0217 (16)	0.0004 (15)	0.0053 (15)	0.0041 (14)
O34	0.050 (2)	0.0264 (19)	0.0201 (17)	0.0125 (18)	0.0072 (18)	0.0022 (15)
O44	0.0272 (18)	0.0167 (16)	0.0263 (17)	0.0040 (14)	−0.0051 (15)	−0.0004 (13)
O54	0.0263 (18)	0.0220 (17)	0.0199 (16)	−0.0013 (14)	−0.0026 (14)	0.0003 (13)
O64	0.029 (2)	0.044 (2)	0.0219 (17)	0.0142 (17)	−0.0034 (16)	−0.0014 (17)
C15	0.025 (2)	0.019 (2)	0.023 (2)	0.0060 (19)	−0.001 (2)	0.0041 (19)
C25	0.026 (2)	0.020 (2)	0.022 (2)	0.0023 (19)	0.003 (2)	−0.0002 (19)
C35	0.027 (3)	0.020 (2)	0.024 (2)	0.003 (2)	−0.001 (2)	−0.0009 (19)
C45	0.022 (2)	0.023 (2)	0.021 (2)	0.0038 (19)	0.002 (2)	0.0002 (18)
C55	0.021 (2)	0.024 (2)	0.027 (2)	0.0007 (19)	0.000 (2)	0.000 (2)
C65	0.035 (3)	0.031 (3)	0.021 (2)	0.002 (2)	0.003 (2)	−0.003 (2)
O25	0.036 (2)	0.031 (2)	0.0240 (18)	−0.0025 (17)	0.0057 (17)	0.0026 (15)
O35	0.034 (2)	0.0212 (18)	0.0242 (17)	0.0006 (15)	0.0031 (16)	0.0003 (14)
O45	0.0209 (17)	0.0190 (17)	0.0273 (17)	0.0029 (13)	−0.0019 (14)	0.0035 (14)
O55	0.0254 (18)	0.0265 (18)	0.0227 (16)	0.0011 (15)	−0.0001 (15)	0.0034 (14)
O65	0.044 (2)	0.033 (2)	0.0291 (19)	0.0056 (18)	0.0045 (18)	0.0042 (16)
C16	0.025 (3)	0.020 (2)	0.025 (2)	0.0047 (19)	0.003 (2)	0.0061 (19)
C26	0.024 (2)	0.022 (2)	0.023 (2)	0.0023 (19)	0.006 (2)	0.0026 (19)
C36	0.021 (2)	0.016 (2)	0.025 (2)	−0.0027 (18)	0.005 (2)	0.0009 (18)
C46	0.022 (2)	0.016 (2)	0.025 (2)	0.0013 (18)	0.004 (2)	0.0036 (18)
C56	0.028 (3)	0.020 (2)	0.022 (2)	0.004 (2)	0.003 (2)	0.0053 (19)
C66	0.028 (3)	0.025 (2)	0.024 (2)	−0.002 (2)	0.004 (2)	0.000 (2)
O26	0.0271 (19)	0.0281 (19)	0.0273 (18)	0.0026 (16)	0.0055 (16)	−0.0038 (15)
O36	0.032 (2)	0.0289 (19)	0.0226 (17)	−0.0009 (16)	0.0031 (16)	−0.0012 (15)
O46	0.0173 (15)	0.0162 (16)	0.0287 (17)	−0.0003 (12)	0.0040 (14)	0.0041 (14)
O56	0.0257 (18)	0.0258 (18)	0.0221 (16)	0.0053 (15)	0.0026 (15)	0.0052 (14)
O66	0.0283 (19)	0.032 (2)	0.0249 (18)	0.0044 (16)	0.0032 (16)	−0.0031 (15)
C17	0.025 (2)	0.020 (2)	0.026 (2)	−0.0031 (19)	0.005 (2)	0.0022 (19)
C27	0.026 (3)	0.023 (2)	0.028 (2)	−0.001 (2)	0.009 (2)	−0.001 (2)
C37	0.033 (3)	0.019 (2)	0.022 (2)	−0.001 (2)	0.005 (2)	−0.0013 (18)
C47	0.023 (2)	0.016 (2)	0.022 (2)	−0.0008 (18)	0.004 (2)	−0.0009 (18)
C57	0.026 (2)	0.019 (2)	0.019 (2)	−0.0015 (19)	−0.001 (2)	0.0018 (18)
C67	0.030 (3)	0.037 (3)	0.022 (2)	0.007 (2)	0.006 (2)	0.000 (2)
O27	0.036 (2)	0.0227 (19)	0.0310 (19)	0.0000 (16)	0.0119 (17)	−0.0029 (15)
O37	0.041 (2)	0.026 (2)	0.0249 (17)	0.0015 (17)	−0.0020 (17)	−0.0002 (15)
O47	0.0212 (16)	0.0158 (15)	0.0260 (16)	0.0009 (13)	0.0007 (15)	0.0001 (13)
O57	0.0270 (18)	0.0235 (17)	0.0235 (16)	0.0006 (14)	0.0052 (15)	0.0068 (14)
O67	0.036 (2)	0.033 (2)	0.040 (2)	0.0073 (17)	0.0154 (18)	0.0122 (18)
C1'	0.023 (3)	0.062 (4)	0.024 (2)	−0.012 (3)	0.003 (2)	−0.014 (3)
C2'	0.046 (4)	0.063 (5)	0.030 (3)	−0.026 (3)	0.003 (3)	−0.011 (3)
C3'	0.049 (4)	0.102 (7)	0.034 (3)	−0.038 (4)	−0.005 (3)	0.000 (4)
O1'A	0.045 (4)	0.047 (4)	0.035 (3)	−0.010 (3)	−0.005 (3)	−0.011 (3)
C4'	0.019 (3)	0.139 (8)	0.020 (3)	−0.016 (4)	−0.004 (2)	−0.013 (4)
O2'	0.035 (2)	0.119 (5)	0.023 (2)	0.004 (3)	−0.0026 (19)	−0.007 (2)
C5'	0.019 (3)	0.133 (8)	0.030 (3)	0.018 (4)	−0.005 (3)	−0.034 (4)
O1'B	0.045 (4)	0.047 (4)	0.035 (3)	−0.010 (3)	−0.005 (3)	−0.011 (3)
C6'	0.021 (3)	0.078 (5)	0.037 (3)	0.005 (3)	−0.002 (3)	−0.030 (3)
C7'	0.022 (3)	0.044 (3)	0.030 (3)	−0.007 (2)	0.001 (2)	−0.009 (2)
C8'	0.025 (3)	0.032 (3)	0.025 (2)	−0.003 (2)	−0.002 (2)	0.000 (2)
C9'	0.024 (2)	0.027 (3)	0.028 (2)	0.001 (2)	0.001 (2)	−0.006 (2)
O3'	0.038 (2)	0.026 (2)	0.033 (2)	−0.0067 (17)	−0.0038 (18)	−0.0010 (16)
C1	0.024 (2)	0.022 (2)	0.020 (2)	−0.0057 (19)	0.000 (2)	0.0028 (19)
O1	0.0229 (18)	0.0232 (18)	0.0245 (16)	−0.0068 (14)	0.0000 (15)	0.0037 (14)
C2	0.023 (2)	0.028 (3)	0.023 (2)	−0.007 (2)	−0.006 (2)	0.0011 (19)
C3	0.019 (2)	0.027 (3)	0.028 (2)	−0.001 (2)	−0.003 (2)	0.006 (2)
O2	0.0238 (18)	0.0277 (19)	0.034 (2)	−0.0006 (15)	−0.0012 (16)	0.0072 (16)
C4	0.022 (2)	0.019 (2)	0.029 (2)	0.0033 (19)	0.003 (2)	0.0024 (19)
O3	0.0272 (19)	0.0223 (18)	0.0328 (19)	0.0051 (15)	0.0096 (16)	0.0000 (15)
C5	0.023 (2)	0.019 (2)	0.022 (2)	−0.0005 (19)	−0.001 (2)	0.0003 (18)
O4	0.0267 (18)	0.0227 (17)	0.0212 (15)	0.0012 (14)	−0.0024 (15)	−0.0015 (14)
C6	0.021 (2)	0.020 (2)	0.022 (2)	0.0047 (19)	−0.0019 (19)	−0.0006 (18)
C7	0.034 (3)	0.024 (3)	0.025 (2)	−0.002 (2)	−0.002 (2)	−0.001 (2)
O5	0.050 (3)	0.040 (2)	0.0216 (18)	−0.011 (2)	0.0026 (18)	−0.0076 (16)
O6	0.067 (3)	0.0209 (19)	0.031 (2)	0.0037 (19)	0.012 (2)	−0.0015 (16)
O1W	0.069 (11)	0.069 (12)	0.035 (8)	−0.030 (9)	0.007 (8)	0.002 (8)
O2W	0.065 (5)	0.084 (6)	0.058 (5)	0.015 (5)	0.022 (4)	0.011 (4)
O8W	0.043 (3)	0.057 (3)	0.043 (2)	0.011 (2)	0.000 (2)	−0.016 (2)
O9W	0.048 (3)	0.050 (3)	0.090 (4)	0.018 (2)	−0.044 (3)	−0.032 (3)
O10A	0.042 (4)	0.035 (3)	0.086 (5)	0.013 (3)	−0.006 (4)	−0.012 (4)
O10B	0.065 (18)	0.029 (12)	0.049 (14)	0.014 (11)	0.003 (14)	0.008 (12)
O11W	0.054 (6)	0.039 (5)	0.048 (5)	0.011 (4)	−0.011 (5)	0.009 (4)
O12W	0.045 (4)	0.071 (6)	0.153 (9)	0.019 (4)	0.026 (5)	0.014 (6)
O13W	0.071 (4)	0.054 (3)	0.060 (3)	−0.023 (3)	−0.028 (3)	0.033 (3)

Geometric parameters (Å, º)

C11—O47	1.415 (6)	C65—H625	0.9900
C11—O51	1.424 (6)	O25—H25O	0.8400
C11—C21	1.531 (7)	O35—H35O	0.8400
C11—H11	1.0000	O45—C16	1.416 (6)
C21—O21	1.415 (6)	O65—H65O	0.8400
C21—C31	1.522 (7)	C16—O56	1.406 (6)
C21—H21	1.0000	C16—C26	1.529 (7)
C31—O31	1.439 (5)	C16—H16	1.0000
C31—C41	1.507 (6)	C26—O26	1.417 (6)
C31—H31	1.0000	C26—C36	1.519 (7)
C41—O41	1.414 (6)	C26—H26	1.0000
C41—C51	1.519 (6)	C36—O36	1.412 (6)
C41—H41	1.0000	C36—C46	1.521 (7)
C51—O51	1.442 (6)	C36—H36	1.0000
C51—C61	1.533 (6)	C46—O46	1.427 (6)
C51—H51	1.0000	C46—C56	1.529 (7)
C61—O61	1.413 (7)	C46—H46	1.0000
C61—H611	0.9900	C56—O56	1.441 (6)
C61—H621	0.9900	C56—C66	1.514 (7)
O21—H21O	0.8400	C56—H56	1.0000
O31—H31O	0.8400	C66—O66	1.419 (6)
O41—C12	1.412 (5)	C66—H616	0.9900
O61—H61O	0.8400	C66—H626	0.9900
C12—O52	1.402 (5)	O26—H26O	0.8400
C12—C22	1.529 (6)	O36—H36O	0.8400
C12—H12	1.0000	O46—C17	1.408 (6)
C22—O22	1.430 (5)	O66—H66O	0.8400
C22—C32	1.492 (7)	C17—O57	1.412 (6)
C22—H22	1.0000	C17—C27	1.512 (7)
C32—O32	1.431 (6)	C17—H17	1.0000
C32—C42	1.513 (6)	C27—O27	1.437 (6)
C32—H32	1.0000	C27—C37	1.519 (7)
C42—O42	1.431 (6)	C27—H27	1.0000
C42—C52	1.523 (7)	C37—O37	1.425 (6)
C42—H42	1.0000	C37—C47	1.525 (6)
C52—O52	1.435 (6)	C37—H37	1.0000
C52—C62	1.522 (7)	C47—O47	1.434 (5)
C52—H52	1.0000	C47—C57	1.512 (7)
C62—O62	1.419 (7)	C47—H47	1.0000
C62—H612	0.9900	C57—O57	1.453 (6)
C62—H622	0.9900	C57—C67	1.515 (7)
O22—H22O	0.8400	C57—H57	1.0000
O32—H32O	0.8400	C67—O67	1.422 (7)
O42—C13	1.415 (6)	C67—H617	0.9900
O62—H62O	0.8400	C67—H627	0.9900
C13—O53	1.412 (6)	O27—H27O	0.8400
C13—C23	1.527 (7)	O37—H37O	0.8400
C13—H13	1.0000	O67—H67O	0.8400
C23—O23	1.424 (6)	C1'—C2'	1.386 (10)
C23—C33	1.510 (7)	C1'—C6'	1.405 (8)
C23—H23	1.0000	C1'—C7'	1.448 (8)
C33—O33	1.418 (6)	C2'—C3'	1.349 (9)
C33—C43	1.517 (6)	C2'—H2'	0.9500
C33—H33	1.0000	C3'—C4'	1.299 (11)
C43—O43	1.429 (6)	C3'—O1'A	1.3475 (14)
C43—C53	1.530 (7)	C3'—H3B	0.9500
C43—H43	1.0000	O1'A—H1A	0.8400
C53—O53	1.431 (6)	C4'—O2'	1.382 (8)
C53—C63	1.503 (6)	C4'—C5'	1.386 (13)
C53—H53	1.0000	O2'—H2'O	0.8400
C63—O63	1.419 (6)	C5'—O1'B	1.3489 (14)
C63—H613	0.9900	C5'—C6'	1.362 (10)
C63—H623	0.9900	C5'—H5A	0.9500
O23—H23O	0.8400	O1'B—H1B	0.8400
O33—H33O	0.8400	C6'—H6'	0.9500
O43—C14	1.399 (6)	C7'—C8'	1.348 (7)
O63—H63O	0.8400	C7'—H7'	0.9500
C14—O54	1.412 (5)	C8'—C9'	1.468 (7)
C14—C24	1.519 (7)	C8'—H8'	0.9500
C14—H14	1.0000	C9'—O3'	1.210 (6)
C24—O24	1.430 (6)	C9'—O4	1.360 (6)
C24—C34	1.519 (7)	C1—O1	1.436 (6)
C24—H24	1.0000	C1—C6	1.521 (6)
C34—O34	1.430 (6)	C1—C7	1.530 (7)
C34—C44	1.509 (6)	C1—C2	1.535 (7)
C34—H34	1.0000	O1—H1O	0.8400
C44—O44	1.432 (6)	C2—C3	1.524 (7)
C44—C54	1.516 (7)	C2—H21E	0.9900
C44—H44	1.0000	C2—H22E	0.9900
C54—O54	1.444 (6)	C3—O2	1.425 (6)
C54—C64	1.512 (6)	C3—C4	1.522 (7)
C54—H54	1.0000	C3—H3	1.0000
C64—O64	1.404 (6)	O2—H2O	0.8400
C64—H614	0.9900	C4—O3	1.427 (6)
C64—H624	0.9900	C4—C5	1.506 (7)
O24—H24O	0.8400	C4—H4	1.0000
O34—H34O	0.8400	O3—H3O	0.8400
O44—C15	1.423 (6)	C5—O4	1.448 (6)
O64—H64O	0.8400	C5—C6	1.518 (7)
C15—O55	1.412 (6)	C5—H5	1.0000
C15—C25	1.523 (7)	C6—H61	0.9900
C15—H15	1.0000	C6—H62	0.9900
C25—O25	1.430 (6)	C7—O5	1.252 (6)
C25—C35	1.496 (7)	C7—O6	1.273 (6)
C25—H25	1.0000	O6—H6O	0.8400
C35—O35	1.423 (6)	O8W—H1W8	0.9605
C35—C45	1.524 (7)	O8W—H2W8	0.9547
C35—H35	1.0000	O9W—H1W9	0.9608
C45—O45	1.434 (6)	O9W—H2W9	0.9585
C45—C55	1.524 (7)	O11W—H111	0.9480
C45—H45	1.0000	O11W—H211	0.9635
C55—O55	1.434 (6)	O12W—H112	0.9605
C55—C65	1.535 (7)	O12W—H212	0.9494
C55—H55	1.0000	O13W—H113	0.9601
C65—O65	1.425 (7)	O13W—H213	0.9610
C65—H615	0.9900
O47—C11—O51	110.5 (4)	O45—C45—H45	109.9
O47—C11—C21	107.5 (4)	C35—C45—H45	109.9
O51—C11—C21	110.6 (4)	C55—C45—H45	109.9
O47—C11—H11	109.4	O55—C55—C45	110.3 (4)
O51—C11—H11	109.4	O55—C55—C65	106.9 (4)
C21—C11—H11	109.4	C45—C55—C65	113.7 (4)
O21—C21—C31	111.7 (4)	O55—C55—H55	108.6
O21—C21—C11	112.2 (4)	C45—C55—H55	108.6
C31—C21—C11	109.1 (4)	C65—C55—H55	108.6
O21—C21—H21	107.9	O65—C65—C55	112.7 (4)
C31—C21—H21	107.9	O65—C65—H615	109.1
C11—C21—H21	107.9	C55—C65—H615	109.1
O31—C31—C41	109.4 (4)	O65—C65—H625	109.1
O31—C31—C21	110.0 (4)	C55—C65—H625	109.1
C41—C31—C21	108.6 (4)	H615—C65—H625	107.8
O31—C31—H31	109.6	C25—O25—H25O	109.5
C41—C31—H31	109.6	C35—O35—H35O	109.5
C21—C31—H31	109.6	C16—O45—C45	118.0 (4)
O41—C41—C31	108.2 (4)	C15—O55—C55	113.0 (4)
O41—C41—C51	109.6 (4)	C65—O65—H65O	109.5
C31—C41—C51	111.3 (4)	O56—C16—O45	110.8 (4)
O41—C41—H41	109.2	O56—C16—C26	111.3 (4)
C31—C41—H41	109.2	O45—C16—C26	109.1 (4)
C51—C41—H41	109.2	O56—C16—H16	108.6
O51—C51—C41	110.5 (4)	O45—C16—H16	108.6
O51—C51—C61	106.0 (4)	C26—C16—H16	108.6
C41—C51—C61	113.1 (4)	O26—C26—C36	111.2 (4)
O51—C51—H51	109.0	O26—C26—C16	108.5 (4)
C41—C51—H51	109.0	C36—C26—C16	111.7 (4)
C61—C51—H51	109.0	O26—C26—H26	108.4
O61—C61—C51	112.5 (4)	C36—C26—H26	108.4
O61—C61—H611	109.1	C16—C26—H26	108.4
C51—C61—H611	109.1	O36—C36—C26	109.5 (4)
O61—C61—H621	109.1	O36—C36—C46	111.7 (4)
C51—C61—H621	109.1	C26—C36—C46	108.6 (4)
H611—C61—H621	107.8	O36—C36—H36	109.0
C21—O21—H21O	109.5	C26—C36—H36	109.0
C31—O31—H31O	109.5	C46—C36—H36	109.0
C12—O41—C41	118.6 (4)	O46—C46—C36	107.5 (4)
C11—O51—C51	114.3 (3)	O46—C46—C56	111.0 (4)
C61—O61—H61O	109.5	C36—C46—C56	108.3 (4)
O52—C12—O41	112.1 (4)	O46—C46—H46	110.0
O52—C12—C22	110.8 (4)	C36—C46—H46	110.0
O41—C12—C22	108.1 (4)	C56—C46—H46	110.0
O52—C12—H12	108.6	O56—C56—C66	105.6 (4)
O41—C12—H12	108.6	O56—C56—C46	107.5 (4)
C22—C12—H12	108.6	C66—C56—C46	116.3 (4)
O22—C22—C32	112.0 (4)	O56—C56—H56	109.1
O22—C22—C12	110.0 (4)	C66—C56—H56	109.1
C32—C22—C12	109.1 (4)	C46—C56—H56	109.1
O22—C22—H22	108.5	O66—C66—C56	110.7 (4)
C32—C22—H22	108.5	O66—C66—H616	109.5
C12—C22—H22	108.5	C56—C66—H616	109.5
O32—C32—C22	108.1 (4)	O66—C66—H626	109.5
O32—C32—C42	111.6 (4)	C56—C66—H626	109.5
C22—C32—C42	108.5 (4)	H616—C66—H626	108.1
O32—C32—H32	109.6	C26—O26—H26O	109.5
C22—C32—H32	109.6	C36—O36—H36O	109.5
C42—C32—H32	109.6	C17—O46—C46	117.4 (4)
O42—C42—C32	108.4 (4)	C16—O56—C56	113.5 (3)
O42—C42—C52	107.9 (4)	C66—O66—H66O	109.5
C32—C42—C52	111.6 (4)	O46—C17—O57	111.6 (4)
O42—C42—H42	109.6	O46—C17—C27	108.4 (4)
C32—C42—H42	109.6	O57—C17—C27	109.8 (4)
C52—C42—H42	109.6	O46—C17—H17	109.0
O52—C52—C62	105.9 (4)	O57—C17—H17	109.0
O52—C52—C42	109.8 (4)	C27—C17—H17	109.0
C62—C52—C42	113.2 (4)	O27—C27—C17	111.1 (4)
O52—C52—H52	109.3	O27—C27—C37	110.7 (4)
C62—C52—H52	109.3	C17—C27—C37	109.7 (4)
C42—C52—H52	109.3	O27—C27—H27	108.4
O62—C62—C52	111.7 (4)	C17—C27—H27	108.4
O62—C62—H612	109.3	C37—C27—H27	108.4
C52—C62—H612	109.3	O37—C37—C27	111.5 (4)
O62—C62—H622	109.3	O37—C37—C47	108.0 (4)
C52—C62—H622	109.3	C27—C37—C47	109.2 (4)
H612—C62—H622	107.9	O37—C37—H37	109.4
C22—O22—H22O	109.5	C27—C37—H37	109.4
C32—O32—H32O	109.5	C47—C37—H37	109.4
C13—O42—C42	117.5 (4)	O47—C47—C57	108.9 (4)
C12—O52—C52	113.2 (3)	O47—C47—C37	106.3 (4)
C62—O62—H62O	109.5	C57—C47—C37	112.8 (4)
O53—C13—O42	110.2 (4)	O47—C47—H47	109.6
O53—C13—C23	110.5 (4)	C57—C47—H47	109.6
O42—C13—C23	108.1 (4)	C37—C47—H47	109.6
O53—C13—H13	109.3	O57—C57—C47	110.8 (4)
O42—C13—H13	109.3	O57—C57—C67	105.5 (4)
C23—C13—H13	109.3	C47—C57—C67	113.6 (4)
O23—C23—C33	109.4 (4)	O57—C57—H57	109.0
O23—C23—C13	109.6 (4)	C47—C57—H57	109.0
C33—C23—C13	108.4 (4)	C67—C57—H57	109.0
O23—C23—H23	109.8	O67—C67—C57	112.4 (4)
C33—C23—H23	109.8	O67—C67—H617	109.1
C13—C23—H23	109.8	C57—C67—H617	109.1
O33—C33—C23	111.7 (4)	O67—C67—H627	109.1
O33—C33—C43	107.8 (4)	C57—C67—H627	109.1
C23—C33—C43	107.9 (4)	H617—C67—H627	107.9
O33—C33—H33	109.8	C27—O27—H27O	109.5
C23—C33—H33	109.8	C37—O37—H37O	109.5
C43—C33—H33	109.8	C11—O47—C47	118.8 (4)
O43—C43—C33	108.6 (4)	C17—O57—C57	114.1 (4)
O43—C43—C53	109.3 (4)	C67—O67—H67O	109.5
C33—C43—C53	111.3 (4)	C2'—C1'—C6'	117.6 (6)
O43—C43—H43	109.2	C2'—C1'—C7'	122.4 (5)
C33—C43—H43	109.2	C6'—C1'—C7'	119.8 (6)
C53—C43—H43	109.2	C3'—C2'—C1'	116.9 (6)
O53—C53—C63	105.7 (4)	C3'—C2'—H2'	121.5
O53—C53—C43	110.2 (4)	C1'—C2'—H2'	121.5
C63—C53—C43	112.8 (4)	C4'—C3'—O1'A	115.8 (7)
O53—C53—H53	109.3	C4'—C3'—C2'	128.4 (8)
C63—C53—H53	109.3	O1'A—C3'—C2'	115.8 (8)
C43—C53—H53	109.3	C4'—C3'—H3B	115.8
O63—C63—C53	111.0 (4)	C2'—C3'—H3B	115.8
O63—C63—H613	109.4	C3'—O1'A—H1A	109.5
C53—C63—H613	109.4	C3'—C4'—O2'	121.0 (9)
O63—C63—H623	109.4	C3'—C4'—C5'	115.4 (6)
C53—C63—H623	109.4	O2'—C4'—C5'	123.6 (7)
H613—C63—H623	108.0	C4'—O2'—H2'O	109.5
C23—O23—H23O	109.5	O1'B—C5'—C6'	134.3 (9)
C33—O33—H33O	109.5	O1'B—C5'—C4'	103.3 (7)
C14—O43—C43	117.3 (4)	C6'—C5'—C4'	121.2 (6)
C13—O53—C53	114.8 (4)	C6'—C5'—H5A	119.4
C63—O63—H63O	109.5	C4'—C5'—H5A	119.4
O43—C14—O54	111.7 (4)	C5'—O1'B—H1B	109.5
O43—C14—C24	109.4 (4)	C5'—C6'—C1'	120.4 (8)
O54—C14—C24	110.7 (4)	C5'—C6'—H6'	119.8
O43—C14—H14	108.3	C1'—C6'—H6'	119.8
O54—C14—H14	108.3	C8'—C7'—C1'	126.1 (6)
C24—C14—H14	108.3	C8'—C7'—H7'	116.9
O24—C24—C14	110.5 (4)	C1'—C7'—H7'	116.9
O24—C24—C34	112.2 (4)	C7'—C8'—C9'	121.3 (5)
C14—C24—C34	110.4 (4)	C7'—C8'—H8'	119.4
O24—C24—H24	107.9	C9'—C8'—H8'	119.4
C14—C24—H24	107.9	O3'—C9'—O4	123.7 (5)
C34—C24—H24	107.9	O3'—C9'—C8'	127.1 (5)
O34—C34—C44	109.5 (4)	O4—C9'—C8'	109.3 (4)
O34—C34—C24	110.8 (4)	O1—C1—C6	111.3 (4)
C44—C34—C24	108.8 (4)	O1—C1—C7	108.6 (4)
O34—C34—H34	109.2	C6—C1—C7	111.4 (4)
C44—C34—H34	109.2	O1—C1—C2	106.3 (4)
C24—C34—H34	109.2	C6—C1—C2	110.6 (4)
O44—C44—C34	107.5 (4)	C7—C1—C2	108.4 (4)
O44—C44—C54	108.5 (4)	C1—O1—H1O	109.5
C34—C44—C54	111.5 (4)	C3—C2—C1	110.5 (4)
O44—C44—H44	109.8	C3—C2—H21E	109.5
C34—C44—H44	109.8	C1—C2—H21E	109.5
C54—C44—H44	109.8	C3—C2—H22E	109.5
O54—C54—C64	106.2 (4)	C1—C2—H22E	109.5
O54—C54—C44	110.4 (4)	H21E—C2—H22E	108.1
C64—C54—C44	114.4 (4)	O2—C3—C4	111.3 (4)
O54—C54—H54	108.6	O2—C3—C2	112.7 (4)
C64—C54—H54	108.6	C4—C3—C2	111.9 (4)
C44—C54—H54	108.6	O2—C3—H3	106.8
O64—C64—C54	113.9 (4)	C4—C3—H3	106.8
O64—C64—H614	108.8	C2—C3—H3	106.8
C54—C64—H614	108.8	C3—O2—H2O	109.5
O64—C64—H624	108.8	O3—C4—C5	112.7 (4)
C54—C64—H624	108.8	O3—C4—C3	111.9 (4)
H614—C64—H624	107.7	C5—C4—C3	110.9 (4)
C24—O24—H24O	109.5	O3—C4—H4	107.0
C34—O34—H34O	109.5	C5—C4—H4	107.0
C15—O44—C44	118.9 (4)	C3—C4—H4	107.0
C14—O54—C54	114.0 (3)	C4—O3—H3O	109.5
C64—O64—H64O	109.5	O4—C5—C4	109.2 (4)
O55—C15—O44	110.8 (4)	O4—C5—C6	105.4 (4)
O55—C15—C25	110.2 (4)	C4—C5—C6	111.4 (4)
O44—C15—C25	106.4 (4)	O4—C5—H5	110.2
O55—C15—H15	109.8	C4—C5—H5	110.2
O44—C15—H15	109.8	C6—C5—H5	110.2
C25—C15—H15	109.8	C9'—O4—C5	117.9 (4)
O25—C25—C35	111.2 (4)	C5—C6—C1	112.4 (4)
O25—C25—C15	109.5 (4)	C5—C6—H61	109.1
C35—C25—C15	109.0 (4)	C1—C6—H61	109.1
O25—C25—H25	109.0	C5—C6—H62	109.1
C35—C25—H25	109.0	C1—C6—H62	109.1
C15—C25—H25	109.0	H61—C6—H62	107.9
O35—C35—C25	110.2 (4)	O5—C7—O6	123.1 (5)
O35—C35—C45	110.6 (4)	O5—C7—C1	121.1 (5)
C25—C35—C45	108.9 (4)	O6—C7—C1	115.8 (4)
O35—C35—H35	109.0	C7—O6—H6O	109.5
C25—C35—H35	109.0	H1W8—O8W—H2W8	105.1
C45—C35—H35	109.0	H1W9—O9W—H2W9	104.7
O45—C45—C35	104.8 (4)	H111—O11W—H211	105.4
O45—C45—C55	110.3 (4)	H112—O12W—H212	105.9
C35—C45—C55	112.0 (4)	H113—O13W—H213	104.7