Per(3-deoxy)-α-cyclomannin: an n-butanol hexahydrate inclusion complex (2024)

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803003763/na6201sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803003763/na6201Isup2.hkl Contains datablock I

CCDC reference: 206803

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Key indicators

Single-crystal X-ray study
T = 211 K
Mean (C-C) = 0.005 Å
H-atom completeness 88%
Disorder in solvent or counterion
R factor = 0.039
wR factor = 0.076
Data-to-parameter ratio = 8.3

checkCIF results

No syntax errors foundADDSYM reports no extra symmetry
 Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 31.00 Perc.General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C40 H82 O31 Atom count from the _atom_site data: C40 H72 O31CELLZ_01 From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C40 H82 O31 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 80.00 80.00 0.00 H 164.00 144.00 20.00 O 62.00 62.00 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional?REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.06 From the CIF: _reflns_number_total 5703 Count of symmetry unique reflns 5746 Completeness (_total/calc) 99.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
 0 Alert Level A = Potentially serious problem
 0 Alert Level B = Potential problem
 1 Alert Level C = Please check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

cyclohexakis[(1→4)–3-deoxy-α-D-arabino-hexopyranosyl] top

Crystal data

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C₃₆H₆₀O₂₄·C₄H₁₀O·6H₂O	F(000) = 1140
M_r = 1059.06	D_x = 1.380 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.3995 (5) Å	Cell parameters from 36831 reflections
b = 24.4481 (18) Å	θ = 1.5–27.1°
c = 14.2649 (8) Å	µ = 0.12 mm⁻¹
β = 99.116 (5)°	T = 211 K
V = 2548.0 (3) Å³	Plate, colourless
Z = 2	0.28 × 0.28 × 0.12 mm

Data collection

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Stoe IPDS-II diffractometer	3750 reflections with I > 2σ(I)
Radiation source: sealed tube X-ray tube 12 x 0.4mm long-fine-focus	R_int = 0.077
Plane graphite monochromator	θ_max = 27.1°, θ_min = 1.5°
Detector resolution: 6.67 pixels mm^-1	h = −9→9
rotation method scans	k = −31→31
36831 measured reflections	l = −17→18
5703 independent reflections

Refinement

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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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0304P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.002
5703 reflections	Δρ_max = 0.36 e Å⁻³
684 parameters	Δρ_min = −0.30 e Å⁻³
33 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0181 (8)

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factorwR and goodness of fit S are based on F², conventionalR-factors R are based on F, with F set to zero fornegative F². The threshold expression of F² >σ(F²) is used only for calculating R-factors(gt) etc.and is not relevant to the choice of reflections for refinement.R-factors based on F² are statistically about twice as largeas those based on F, and R- factors based on ALL data will beeven larger.

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

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	x	y	z	U_iso*/U_eq	Occ. (<1)
O4F	0.2225 (3)	0.31185 (9)	0.28173 (16)	0.0322 (6)
C1A	0.1623 (5)	0.27395 (14)	0.2093 (2)	0.0312 (8)
H1A	0.1369	0.2386	0.2385	0.037*
C2A	0.3166 (5)	0.26621 (14)	0.1523 (3)	0.0343 (8)
H2A	0.4301	0.2564	0.1956	0.041*
O2A	0.2697 (5)	0.22328 (11)	0.08454 (19)	0.0502 (8)
H2O1	0.3022	0.1934	0.1094	0.060*
C3A	0.3477 (5)	0.31795 (15)	0.0997 (3)	0.0348 (8)
H3A1	0.4348	0.3105	0.0562	0.042*
H3A2	0.4021	0.3456	0.1454	0.042*
C4A	0.1716 (5)	0.34044 (13)	0.0435 (3)	0.0303 (8)
H4A	0.1324	0.3178	−0.0136	0.036*
C5A	0.0208 (5)	0.34344 (14)	0.1037 (3)	0.0321 (8)
H5A	0.0522	0.3723	0.1523	0.039*
O5A	0.0007 (3)	0.29237 (9)	0.15094 (17)	0.0335 (6)
C6A	−0.1642 (5)	0.35617 (15)	0.0474 (3)	0.0406 (9)
H6A1	−0.2545	0.3580	0.0906	0.049*
H6A2	−0.1597	0.3921	0.0175	0.049*
O6A	−0.2219 (4)	0.31641 (11)	−0.02437 (19)	0.0490 (7)
H6O1	−0.2117	0.2853	−0.0006	0.059*
O4A	0.2034 (4)	0.39577 (9)	0.01662 (17)	0.0386 (6)
C1B	0.2172 (5)	0.40684 (14)	−0.0790 (2)	0.0327 (8)
H1B	0.2160	0.3718	−0.1139	0.039*
C2B	0.3992 (5)	0.43492 (14)	−0.0801 (3)	0.0338 (8)
H2B	0.4969	0.4126	−0.0430	0.041*
O2B	0.4337 (4)	0.43879 (11)	−0.17533 (18)	0.0444 (7)
H2O2	0.4990	0.4128	−0.1867	0.053*
C3B	0.3982 (5)	0.49086 (15)	−0.0343 (3)	0.0349 (8)
H3B1	0.5075	0.5110	−0.0452	0.042*
H3B2	0.4047	0.4863	0.0344	0.042*
C4B	0.2283 (5)	0.52446 (13)	−0.0726 (2)	0.0299 (8)
H4B	0.2378	0.5389	−0.1365	0.036*
C5B	0.0543 (4)	0.49150 (14)	−0.0757 (3)	0.0320 (8)
H5B	0.0327	0.4850	−0.0099	0.038*
O5B	0.0692 (3)	0.43910 (9)	−0.12140 (17)	0.0347 (6)
C6B	−0.1131 (5)	0.51864 (16)	−0.1308 (3)	0.0399 (9)
H6B1	−0.2188	0.4943	−0.1322	0.048*
H6B2	−0.1388	0.5525	−0.0984	0.048*
O6B	−0.0885 (4)	0.53099 (12)	−0.2253 (2)	0.0567 (8)
H6O2	−0.0510	0.5629	−0.2278	0.068*
O4B	0.2312 (4)	0.56883 (9)	−0.00572 (17)	0.0354 (6)
C1C	0.1633 (5)	0.62024 (13)	−0.0388 (3)	0.0323 (8)
H1C	0.1384	0.6196	−0.1091	0.039*
C2C	0.3123 (5)	0.66169 (14)	−0.0070 (3)	0.0331 (8)
H2C	0.4267	0.6500	−0.0290	0.040*
O2C	0.2604 (4)	0.71465 (10)	−0.04514 (18)	0.0444 (7)
H2O3	0.2488	0.7136	−0.1039	0.053*
C3C	0.3450 (5)	0.66581 (15)	0.1002 (2)	0.0330 (8)
H3C1	0.4012	0.6318	0.1272	0.040*
H3C2	0.4302	0.6959	0.1198	0.040*
C4C	0.1681 (5)	0.67571 (14)	0.1383 (2)	0.0284 (8)
H4C	0.1254	0.7136	0.1242	0.034*
C5C	0.0185 (5)	0.63501 (14)	0.0977 (2)	0.0321 (8)
H5C	0.0534	0.5981	0.1230	0.038*
O5C	0.0000 (3)	0.63362 (9)	−0.00432 (17)	0.0328 (6)
C6C	−0.1675 (5)	0.64918 (14)	0.1211 (3)	0.0365 (9)
H6C1	−0.2596	0.6262	0.0827	0.044*
H6C2	−0.1698	0.6407	0.1880	0.044*
O6C	−0.2158 (4)	0.70547 (10)	0.10437 (18)	0.0415 (6)
H6O3	−0.2254	0.7121	0.0467	0.050*
O4C	0.2102 (3)	0.66758 (9)	0.24001 (16)	0.0316 (6)
C1D	0.1384 (5)	0.70530 (13)	0.3004 (2)	0.0291 (8)
H1D	0.0943	0.7382	0.2632	0.035*
C2D	0.2933 (5)	0.72126 (13)	0.3763 (2)	0.0288 (8)
H2D	0.3942	0.7368	0.3467	0.035*
O2D	0.2344 (4)	0.76077 (10)	0.43948 (17)	0.0378 (6)
H2O4	0.1993	0.7889	0.4094	0.045*
C3D	0.3611 (5)	0.67089 (13)	0.4340 (2)	0.0296 (8)
H3D1	0.4189	0.6458	0.3941	0.036*
H3D2	0.4540	0.6819	0.4875	0.036*
C4D	0.2072 (5)	0.64144 (13)	0.4715 (2)	0.0283 (8)
H4D	0.1737	0.6618	0.5263	0.034*
C5D	0.0381 (5)	0.63395 (13)	0.3962 (2)	0.0291 (8)
H5D	0.0610	0.6036	0.3537	0.035*
O5D	−0.0084 (3)	0.68235 (9)	0.33964 (16)	0.0296 (5)
C6D	−0.1320 (5)	0.62111 (15)	0.4380 (3)	0.0364 (9)
H6D1	−0.2377	0.6210	0.3870	0.044*
H6D2	−0.1205	0.5844	0.4658	0.044*
O6D	−0.1644 (4)	0.65909 (11)	0.50879 (18)	0.0410 (6)
H6O4	−0.1928	0.6892	0.4838	0.049*
O4D	0.2756 (3)	0.58788 (9)	0.50200 (16)	0.0307 (6)
C1E	0.2629 (5)	0.57213 (14)	0.5958 (2)	0.0298 (8)
H1E	0.2589	0.6055	0.6347	0.036*
C2E	0.4346 (5)	0.54019 (14)	0.6341 (2)	0.0308 (8)
H2E	0.5422	0.5611	0.6205	0.037*
O2E	0.4451 (4)	0.53597 (10)	0.73517 (18)	0.0423 (6)
H2O5	0.4708	0.5041	0.7521	0.051*
C3E	0.4344 (4)	0.48489 (14)	0.5867 (3)	0.0308 (8)
H3E1	0.5356	0.4629	0.6197	0.037*
H3E2	0.4546	0.4898	0.5209	0.037*
C4E	0.2552 (5)	0.45440 (13)	0.5871 (3)	0.0280 (8)
H4E	0.2450	0.4426	0.6524	0.034*
C5E	0.0935 (4)	0.48971 (14)	0.5477 (2)	0.0300 (8)
H5E	0.0987	0.4977	0.4801	0.036*
O5E	0.1021 (3)	0.54085 (9)	0.60000 (17)	0.0310 (5)
C6E	−0.0926 (5)	0.46611 (14)	0.5557 (3)	0.0344 (8)
H6E1	−0.1865	0.4938	0.5359	0.041*
H6E2	−0.1168	0.4349	0.5123	0.041*
O6E	−0.1062 (4)	0.44867 (11)	0.64923 (19)	0.0458 (7)
H6O5	−0.0765	0.4742	0.6870	0.055*
O4E	0.2658 (3)	0.40715 (9)	0.52746 (16)	0.0318 (6)
C1F	0.1890 (5)	0.35722 (13)	0.5528 (3)	0.0307 (8)
H1F	0.1683	0.3595	0.6196	0.037*
C2F	0.3285 (5)	0.31301 (13)	0.5446 (2)	0.0301 (8)
H2F	0.4454	0.3218	0.5859	0.036*
O2F	0.2604 (4)	0.26115 (9)	0.57169 (17)	0.0364 (6)
H2O6	0.2488	0.2621	0.6286	0.044*
C3F	0.3581 (5)	0.30864 (15)	0.4428 (2)	0.0309 (8)
H3F1	0.4375	0.2772	0.4363	0.037*
H3F2	0.4208	0.3416	0.4258	0.037*
C4F	0.1809 (5)	0.30196 (14)	0.3752 (2)	0.0283 (8)
H4F	0.1353	0.2641	0.3792	0.034*
C5F	0.0331 (5)	0.34242 (14)	0.3942 (2)	0.0305 (8)
H5F	0.0639	0.3791	0.3717	0.037*
O5F	0.0217 (3)	0.34577 (9)	0.49425 (17)	0.0307 (5)
C6F	−0.1578 (5)	0.32750 (15)	0.3469 (3)	0.0380 (9)
H6F1	−0.2450	0.3537	0.3663	0.046*
H6F2	−0.1646	0.3303	0.2779	0.046*
O6F	−0.2094 (4)	0.27375 (11)	0.37012 (18)	0.0419 (6)
H6O6	−0.2189	0.2724	0.4273	0.050*
O1W	−0.2321 (4)	0.19112 (11)	0.24343 (19)	0.0455 (7)
H11W	−0.126 (4)	0.1721 (13)	0.258 (3)	0.055*
H12W	−0.216 (5)	0.2220 (11)	0.278 (3)	0.055*
O2W	0.5907 (4)	0.33858 (11)	0.80191 (19)	0.0387 (6)
H21W	0.648 (5)	0.3291 (16)	0.8611 (14)	0.046*
H22W	0.678 (4)	0.3350 (17)	0.766 (2)	0.046*
O3W	0.2425 (4)	0.28763 (11)	0.76561 (19)	0.0449 (7)
H31W	0.356 (3)	0.3028 (14)	0.777 (3)	0.054*
H32W	0.251 (5)	0.2581 (12)	0.804 (3)	0.054*
O4W	0.1082 (4)	0.13764 (12)	0.2971 (2)	0.0522 (8)
H41W	0.219 (4)	0.1414 (19)	0.278 (3)	0.063*
H42W	0.125 (5)	0.1439 (19)	0.3592 (15)	0.063*
O5W	0.8832 (4)	0.34154 (11)	0.7026 (2)	0.0453 (7)
H51W	0.871 (5)	0.3763 (9)	0.688 (3)	0.054*
H52W	1.000 (3)	0.3347 (15)	0.729 (3)	0.054*
O6W	0.4265 (4)	0.13750 (13)	0.2063 (2)	0.0566 (8)
H61W	0.535 (4)	0.1565 (14)	0.223 (3)	0.068*
H62W	0.455 (5)	0.1024 (8)	0.214 (3)	0.068*
O11L	0.793 (5)	0.4946 (16)	0.222 (3)	0.318 (16)*	0.50
C11L	0.607 (5)	0.5175 (15)	0.246 (2)	0.250 (14)*	0.50
C21L	0.487 (4)	0.4693 (12)	0.288 (2)	0.195 (10)*	0.50
C31L	0.307 (4)	0.5124 (12)	0.292 (2)	0.190 (10)*	0.50
C41L	0.208 (3)	0.4876 (14)	0.207 (2)	0.217 (11)*	0.50
O12L	0.869 (5)	0.4853 (17)	0.185 (3)	0.36 (2)*	0.50
C12L	0.822 (5)	0.479 (2)	0.276 (3)	0.31 (3)*	0.50
C22L	0.603 (4)	0.4683 (13)	0.245 (2)	0.211 (12)*	0.50
C32L	0.461 (4)	0.5154 (10)	0.2769 (18)	0.174 (9)*	0.50
C42L	0.310 (3)	0.4701 (11)	0.281 (2)	0.176 (9)*	0.50

Atomic displacement parameters (Å²)

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	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4F	0.0420 (15)	0.0297 (12)	0.0251 (13)	−0.0051 (11)	0.0055 (11)	−0.0014 (10)
C1A	0.037 (2)	0.0286 (17)	0.0257 (19)	−0.0021 (15)	−0.0014 (16)	0.0001 (15)
C2A	0.041 (2)	0.0325 (19)	0.029 (2)	0.0044 (16)	0.0040 (16)	−0.0021 (16)
O2A	0.087 (2)	0.0293 (13)	0.0345 (16)	0.0088 (14)	0.0091 (15)	−0.0024 (12)
C3A	0.038 (2)	0.0345 (19)	0.034 (2)	0.0015 (16)	0.0129 (17)	0.0003 (16)
C4A	0.042 (2)	0.0197 (16)	0.031 (2)	−0.0016 (15)	0.0115 (17)	0.0031 (14)
C5A	0.037 (2)	0.0289 (17)	0.0305 (19)	0.0007 (15)	0.0065 (17)	0.0049 (15)
O5A	0.0354 (14)	0.0324 (12)	0.0314 (14)	−0.0058 (10)	0.0014 (11)	0.0085 (10)
C6A	0.035 (2)	0.038 (2)	0.047 (2)	0.0018 (17)	−0.0003 (18)	0.0011 (18)
O6A	0.0566 (18)	0.0417 (15)	0.0428 (16)	−0.0088 (14)	−0.0097 (14)	0.0099 (13)
O4A	0.0670 (18)	0.0231 (12)	0.0283 (14)	−0.0036 (12)	0.0160 (13)	0.0036 (10)
C1B	0.048 (2)	0.0263 (18)	0.0254 (19)	0.0016 (16)	0.0108 (17)	0.0004 (15)
C2B	0.043 (2)	0.0295 (18)	0.030 (2)	0.0057 (16)	0.0097 (17)	0.0045 (15)
O2B	0.0595 (18)	0.0388 (15)	0.0403 (16)	0.0136 (13)	0.0247 (13)	0.0057 (12)
C3B	0.0355 (19)	0.0302 (18)	0.039 (2)	0.0037 (17)	0.0069 (17)	−0.0014 (16)
C4B	0.040 (2)	0.0237 (17)	0.0275 (19)	0.0024 (15)	0.0088 (17)	−0.0026 (14)
C5B	0.0365 (19)	0.0262 (17)	0.035 (2)	0.0015 (16)	0.0094 (16)	−0.0034 (16)
O5B	0.0405 (15)	0.0285 (12)	0.0333 (14)	0.0010 (11)	0.0006 (12)	−0.0006 (11)
C6B	0.039 (2)	0.040 (2)	0.041 (2)	0.0016 (17)	0.0068 (19)	−0.0029 (17)
O6B	0.068 (2)	0.0579 (19)	0.0430 (18)	0.0072 (16)	0.0054 (15)	0.0149 (14)
O4B	0.0539 (17)	0.0234 (12)	0.0285 (13)	0.0074 (11)	0.0049 (12)	−0.0029 (10)
C1C	0.038 (2)	0.0270 (18)	0.032 (2)	0.0075 (15)	0.0068 (17)	0.0023 (15)
C2C	0.037 (2)	0.0300 (18)	0.033 (2)	0.0003 (15)	0.0093 (17)	−0.0004 (15)
O2C	0.072 (2)	0.0297 (14)	0.0321 (15)	0.0015 (12)	0.0108 (15)	0.0029 (11)
C3C	0.034 (2)	0.0352 (19)	0.030 (2)	−0.0039 (16)	0.0063 (16)	−0.0011 (16)
C4C	0.0319 (19)	0.0276 (17)	0.0261 (19)	−0.0002 (14)	0.0058 (15)	0.0001 (14)
C5C	0.034 (2)	0.0328 (18)	0.029 (2)	−0.0003 (16)	0.0059 (16)	0.0012 (15)
O5C	0.0343 (14)	0.0371 (13)	0.0269 (13)	0.0015 (11)	0.0043 (11)	−0.0058 (11)
C6C	0.033 (2)	0.038 (2)	0.038 (2)	−0.0016 (16)	0.0041 (17)	−0.0003 (16)
O6C	0.0424 (15)	0.0487 (16)	0.0342 (15)	0.0098 (12)	0.0087 (13)	−0.0032 (12)
O4C	0.0408 (15)	0.0326 (13)	0.0221 (13)	0.0063 (10)	0.0066 (11)	−0.0010 (10)
C1D	0.038 (2)	0.0256 (17)	0.0258 (19)	0.0018 (15)	0.0122 (16)	−0.0009 (14)
C2D	0.0330 (19)	0.0259 (16)	0.0274 (19)	0.0031 (14)	0.0044 (16)	−0.0001 (14)
O2D	0.0515 (16)	0.0288 (13)	0.0325 (15)	0.0054 (11)	0.0051 (13)	−0.0021 (11)
C3D	0.0303 (19)	0.0266 (17)	0.031 (2)	−0.0002 (14)	0.0032 (16)	0.0041 (15)
C4D	0.0308 (19)	0.0208 (16)	0.032 (2)	0.0021 (14)	0.0015 (16)	0.0006 (14)
C5D	0.0317 (19)	0.0246 (16)	0.031 (2)	−0.0002 (15)	0.0041 (16)	0.0041 (14)
O5D	0.0300 (13)	0.0298 (12)	0.0294 (13)	0.0022 (10)	0.0058 (11)	0.0047 (10)
C6D	0.034 (2)	0.0344 (19)	0.042 (2)	−0.0011 (16)	0.0080 (18)	0.0020 (16)
O6D	0.0424 (16)	0.0435 (15)	0.0398 (16)	0.0081 (12)	0.0151 (13)	0.0085 (12)
O4D	0.0404 (14)	0.0248 (12)	0.0276 (13)	0.0051 (10)	0.0077 (11)	0.0052 (10)
C1E	0.036 (2)	0.0269 (18)	0.027 (2)	−0.0009 (15)	0.0060 (16)	0.0036 (14)
C2E	0.035 (2)	0.0297 (18)	0.027 (2)	−0.0063 (15)	0.0032 (16)	0.0032 (15)
O2E	0.0566 (17)	0.0361 (14)	0.0317 (15)	−0.0007 (13)	−0.0010 (13)	0.0048 (11)
C3E	0.0282 (17)	0.0293 (18)	0.034 (2)	0.0029 (16)	0.0013 (15)	−0.0004 (16)
C4E	0.033 (2)	0.0246 (17)	0.0257 (19)	−0.0024 (14)	0.0036 (15)	−0.0045 (14)
C5E	0.0330 (18)	0.0275 (17)	0.0303 (19)	−0.0015 (16)	0.0069 (16)	−0.0028 (15)
O5E	0.0333 (13)	0.0248 (12)	0.0364 (14)	−0.0014 (10)	0.0095 (11)	−0.0014 (10)
C6E	0.034 (2)	0.0314 (18)	0.038 (2)	0.0022 (15)	0.0051 (17)	−0.0025 (15)
O6E	0.0459 (17)	0.0506 (16)	0.0432 (17)	−0.0099 (14)	0.0142 (14)	0.0030 (13)
O4E	0.0418 (15)	0.0240 (12)	0.0321 (14)	−0.0041 (10)	0.0134 (11)	−0.0041 (10)
C1F	0.035 (2)	0.0246 (17)	0.034 (2)	−0.0043 (15)	0.0078 (16)	−0.0017 (15)
C2F	0.0352 (19)	0.0251 (16)	0.0293 (19)	−0.0017 (15)	0.0030 (16)	0.0012 (14)
O2F	0.0543 (16)	0.0273 (13)	0.0286 (14)	−0.0004 (11)	0.0094 (13)	0.0039 (10)
C3F	0.0297 (19)	0.0334 (18)	0.029 (2)	0.0030 (15)	0.0039 (16)	0.0002 (15)
C4F	0.036 (2)	0.0295 (18)	0.0200 (18)	−0.0009 (15)	0.0062 (15)	0.0035 (14)
C5F	0.034 (2)	0.0308 (17)	0.028 (2)	0.0032 (15)	0.0081 (16)	0.0020 (15)
O5F	0.0307 (13)	0.0313 (12)	0.0306 (13)	−0.0003 (10)	0.0066 (11)	−0.0036 (10)
C6F	0.031 (2)	0.044 (2)	0.039 (2)	−0.0004 (16)	0.0049 (18)	−0.0024 (16)
O6F	0.0448 (15)	0.0487 (16)	0.0342 (15)	−0.0144 (13)	0.0119 (13)	−0.0102 (12)
O1W	0.0605 (19)	0.0381 (16)	0.0377 (16)	−0.0068 (13)	0.0077 (14)	−0.0033 (12)
O2W	0.0454 (16)	0.0397 (15)	0.0316 (15)	0.0046 (12)	0.0081 (13)	0.0032 (12)
O3W	0.0497 (18)	0.0434 (17)	0.0401 (17)	−0.0093 (13)	0.0020 (14)	0.0040 (12)
O4W	0.068 (2)	0.0495 (17)	0.0417 (17)	−0.0076 (15)	0.0173 (16)	−0.0005 (14)
O5W	0.0573 (19)	0.0330 (15)	0.0474 (17)	−0.0019 (13)	0.0135 (15)	−0.0008 (13)
O6W	0.055 (2)	0.0456 (18)	0.066 (2)	0.0011 (15)	0.0009 (17)	0.0149 (16)

Geometric parameters (Å, º)

top

O4F—C1A	1.406 (4)	C3D—H3D1	0.9800
O4F—C4F	1.436 (4)	C3D—H3D2	0.9800
C1A—O5A	1.418 (4)	C4D—O4D	1.446 (4)
C1A—C2A	1.515 (5)	C4D—C5D	1.525 (5)
C1A—H1A	0.9900	C4D—H4D	0.9900
C2A—O2A	1.432 (4)	C5D—O5D	1.443 (4)
C2A—C3A	1.507 (5)	C5D—C6D	1.509 (5)
C2A—H2A	0.9900	C5D—H5D	0.9900
O2A—H2O1	0.8300	C6D—O6D	1.420 (4)
C3A—C4A	1.520 (5)	C6D—H6D1	0.9800
C3A—H3A1	0.9800	C6D—H6D2	0.9800
C3A—H3A2	0.9800	O6D—H6O4	0.8300
C4A—O4A	1.436 (4)	O4D—C1E	1.409 (4)
C4A—C5A	1.513 (5)	C1E—O5E	1.424 (4)
C4A—H4A	0.9900	C1E—C2E	1.518 (5)
C5A—O5A	1.438 (4)	C1E—H1E	0.9900
C5A—C6A	1.506 (5)	C2E—O2E	1.435 (4)
C5A—H5A	0.9900	C2E—C3E	1.512 (5)
C6A—O6A	1.427 (5)	C2E—H2E	0.9900
C6A—H6A1	0.9800	O2E—H2O5	0.8300
C6A—H6A2	0.9800	C3E—C4E	1.522 (5)
O6A—H6O1	0.8300	C3E—H3E1	0.9800
O4A—C1B	1.410 (4)	C3E—H3E2	0.9800
C1B—O5B	1.406 (4)	C4E—O4E	1.444 (4)
C1B—C2B	1.514 (5)	C4E—C5E	1.510 (5)
C1B—H1B	0.9900	C4E—H4E	0.9900
C2B—O2B	1.425 (4)	C5E—O5E	1.452 (4)
C2B—C3B	1.516 (5)	C5E—C6E	1.514 (5)
C2B—H2B	0.9900	C5E—H5E	0.9900
O2B—H2O2	0.8300	C6E—O6E	1.420 (4)
C3B—C4B	1.528 (5)	C6E—H6E1	0.9800
C3B—H3B1	0.9800	C6E—H6E2	0.9800
C3B—H3B2	0.9800	O6E—H6O5	0.8300
C4B—O4B	1.443 (4)	O4E—C1F	1.418 (4)
C4B—C5B	1.514 (5)	C1F—O5F	1.408 (4)
C4B—H4B	0.9900	C1F—C2F	1.512 (5)
C5B—O5B	1.449 (4)	C1F—H1F	0.9900
C5B—C6B	1.511 (5)	C2F—O2F	1.440 (4)
C5B—H5B	0.9900	C2F—C3F	1.506 (5)
C6B—O6B	1.422 (5)	C2F—H2F	0.9900
C6B—H6B1	0.9800	O2F—H2O6	0.8300
C6B—H6B2	0.9800	C3F—C4F	1.508 (5)
O6B—H6O2	0.8300	C3F—H3F1	0.9800
O4B—C1C	1.407 (4)	C3F—H3F2	0.9800
C1C—O5C	1.413 (4)	C4F—C5F	1.530 (5)
C1C—C2C	1.513 (5)	C4F—H4F	0.9900
C1C—H1C	0.9900	C5F—O5F	1.445 (4)
C2C—O2C	1.433 (4)	C5F—C6F	1.511 (5)
C2C—C3C	1.514 (5)	C5F—H5F	0.9900
C2C—H2C	0.9900	C6F—O6F	1.422 (4)
O2C—H2O3	0.8300	C6F—H6F1	0.9800
C3C—C4C	1.514 (5)	C6F—H6F2	0.9800
C3C—H3C1	0.9800	O6F—H6O6	0.8300
C3C—H3C2	0.9800	O1W—H11W	0.908 (19)
C4C—O4C	1.449 (4)	O1W—H12W	0.898 (19)
C4C—C5C	1.532 (5)	O2W—H21W	0.912 (18)
C4C—H4C	0.9900	O2W—H22W	0.891 (19)
C5C—O5C	1.441 (4)	O3W—H31W	0.906 (19)
C5C—C6C	1.507 (5)	O3W—H32W	0.906 (19)
C5C—H5C	0.9900	O4W—H41W	0.907 (19)
C6C—O6C	1.432 (4)	O4W—H42W	0.889 (19)
C6C—H6C1	0.9800	O5W—H51W	0.877 (18)
C6C—H6C2	0.9800	O5W—H52W	0.902 (19)
O6C—H6O3	0.8300	O6W—H61W	0.924 (19)
O4C—C1D	1.421 (4)	O6W—H62W	0.888 (19)
C1D—O5D	1.415 (4)	O11L—C11L	1.58 (3)
C1D—C2D	1.498 (5)	C11L—C21L	1.65 (3)
C1D—H1D	0.9900	C21L—C31L	1.71 (3)
C2D—O2D	1.435 (4)	C31L—C41L	1.44 (3)
C2D—C3D	1.522 (5)	O12L—C12L	1.41 (4)
C2D—H2D	0.9900	C12L—C22L	1.63 (3)
O2D—H2O4	0.8300	C22L—C32L	1.67 (3)
C3D—C4D	1.515 (5)	C32L—C42L	1.58 (3)

C1A—O4F—C4F	118.8 (3)	C2D—C1D—H1D	109.0
O4F—C1A—O5A	111.2 (3)	O2D—C2D—C1D	110.9 (3)
O4F—C1A—C2A	107.4 (3)	O2D—C2D—C3D	108.2 (3)
O5A—C1A—C2A	111.2 (3)	C1D—C2D—C3D	109.2 (3)
O4F—C1A—H1A	109.0	O2D—C2D—H2D	109.5
O5A—C1A—H1A	109.0	C1D—C2D—H2D	109.5
C2A—C1A—H1A	109.0	C3D—C2D—H2D	109.5
O2A—C2A—C3A	108.6 (3)	C2D—O2D—H2O4	109.5
O2A—C2A—C1A	109.4 (3)	C4D—C3D—C2D	111.9 (3)
C3A—C2A—C1A	110.5 (3)	C4D—C3D—H3D1	109.2
O2A—C2A—H2A	109.5	C2D—C3D—H3D1	109.2
C3A—C2A—H2A	109.5	C4D—C3D—H3D2	109.2
C1A—C2A—H2A	109.5	C2D—C3D—H3D2	109.2
C2A—O2A—H2O1	109.5	H3D1—C3D—H3D2	107.9
C2A—C3A—C4A	112.3 (3)	O4D—C4D—C3D	106.8 (3)
C2A—C3A—H3A1	109.1	O4D—C4D—C5D	108.2 (3)
C4A—C3A—H3A1	109.1	C3D—C4D—C5D	112.8 (3)
C2A—C3A—H3A2	109.1	O4D—C4D—H4D	109.7
C4A—C3A—H3A2	109.1	C3D—C4D—H4D	109.7
H3A1—C3A—H3A2	107.9	C5D—C4D—H4D	109.7
O4A—C4A—C5A	105.8 (3)	O5D—C5D—C6D	104.6 (3)
O4A—C4A—C3A	108.6 (3)	O5D—C5D—C4D	113.1 (3)
C5A—C4A—C3A	111.5 (3)	C6D—C5D—C4D	112.9 (3)
O4A—C4A—H4A	110.3	O5D—C5D—H5D	108.7
C5A—C4A—H4A	110.3	C6D—C5D—H5D	108.7
C3A—C4A—H4A	110.3	C4D—C5D—H5D	108.7
O5A—C5A—C6A	106.0 (3)	C1D—O5D—C5D	114.6 (2)
O5A—C5A—C4A	111.4 (3)	O6D—C6D—C5D	113.0 (3)
C6A—C5A—C4A	113.4 (3)	O6D—C6D—H6D1	109.0
O5A—C5A—H5A	108.6	C5D—C6D—H6D1	109.0
C6A—C5A—H5A	108.6	O6D—C6D—H6D2	109.0
C4A—C5A—H5A	108.6	C5D—C6D—H6D2	109.0
C1A—O5A—C5A	114.2 (3)	H6D1—C6D—H6D2	107.8
O6A—C6A—C5A	112.7 (3)	C6D—O6D—H6O4	109.5
O6A—C6A—H6A1	109.1	C1E—O4D—C4D	117.4 (3)
C5A—C6A—H6A1	109.1	O4D—C1E—O5E	111.7 (3)
O6A—C6A—H6A2	109.1	O4D—C1E—C2E	107.8 (3)
C5A—C6A—H6A2	109.1	O5E—C1E—C2E	111.5 (3)
H6A1—C6A—H6A2	107.8	O4D—C1E—H1E	108.6
C6A—O6A—H6O1	109.5	O5E—C1E—H1E	108.6
C1B—O4A—C4A	118.7 (3)	C2E—C1E—H1E	108.6
O5B—C1B—O4A	110.7 (3)	O2E—C2E—C3E	112.4 (3)
O5B—C1B—C2B	112.0 (3)	O2E—C2E—C1E	107.9 (3)
O4A—C1B—C2B	107.3 (3)	C3E—C2E—C1E	110.9 (3)
O5B—C1B—H1B	108.9	O2E—C2E—H2E	108.5
O4A—C1B—H1B	108.9	C3E—C2E—H2E	108.5
C2B—C1B—H1B	108.9	C1E—C2E—H2E	108.5
O2B—C2B—C1B	109.5 (3)	C2E—O2E—H2O5	109.5
O2B—C2B—C3B	111.4 (3)	C2E—C3E—C4E	112.1 (3)
C1B—C2B—C3B	109.9 (3)	C2E—C3E—H3E1	109.2
O2B—C2B—H2B	108.7	C4E—C3E—H3E1	109.2
C1B—C2B—H2B	108.7	C2E—C3E—H3E2	109.2
C3B—C2B—H2B	108.7	C4E—C3E—H3E2	109.2
C2B—O2B—H2O2	109.5	H3E1—C3E—H3E2	107.9
C2B—C3B—C4B	113.0 (3)	O4E—C4E—C5E	110.6 (3)
C2B—C3B—H3B1	109.0	O4E—C4E—C3E	105.1 (3)
C4B—C3B—H3B1	109.0	C5E—C4E—C3E	111.0 (3)
C2B—C3B—H3B2	109.0	O4E—C4E—H4E	110.0
C4B—C3B—H3B2	109.0	C5E—C4E—H4E	110.0
H3B1—C3B—H3B2	107.8	C3E—C4E—H4E	110.0
O4B—C4B—C5B	110.1 (3)	O5E—C5E—C4E	109.5 (3)
O4B—C4B—C3B	104.1 (3)	O5E—C5E—C6E	104.8 (3)
C5B—C4B—C3B	111.9 (3)	C4E—C5E—C6E	115.5 (3)
O4B—C4B—H4B	110.2	O5E—C5E—H5E	108.9
C5B—C4B—H4B	110.2	C4E—C5E—H5E	108.9
C3B—C4B—H4B	110.2	C6E—C5E—H5E	108.9
O5B—C5B—C6B	105.6 (3)	C1E—O5E—C5E	114.2 (2)
O5B—C5B—C4B	111.0 (3)	O6E—C6E—C5E	112.7 (3)
C6B—C5B—C4B	113.9 (3)	O6E—C6E—H6E1	109.1
O5B—C5B—H5B	108.7	C5E—C6E—H6E1	109.1
C6B—C5B—H5B	108.7	O6E—C6E—H6E2	109.1
C4B—C5B—H5B	108.7	C5E—C6E—H6E2	109.1
C1B—O5B—C5B	114.3 (3)	H6E1—C6E—H6E2	107.8
O6B—C6B—C5B	111.6 (3)	C6E—O6E—H6O5	109.5
O6B—C6B—H6B1	109.3	C1F—O4E—C4E	118.5 (2)
C5B—C6B—H6B1	109.3	O5F—C1F—O4E	111.7 (3)
O6B—C6B—H6B2	109.3	O5F—C1F—C2F	111.0 (3)
C5B—C6B—H6B2	109.3	O4E—C1F—C2F	106.8 (3)
H6B1—C6B—H6B2	108.0	O5F—C1F—H1F	109.1
C6B—O6B—H6O2	109.5	O4E—C1F—H1F	109.1
C1C—O4B—C4B	118.9 (3)	C2F—C1F—H1F	109.1
O4B—C1C—O5C	111.7 (3)	O2F—C2F—C3F	107.9 (3)
O4B—C1C—C2C	107.1 (3)	O2F—C2F—C1F	109.7 (3)
O5C—C1C—C2C	111.3 (3)	C3F—C2F—C1F	109.3 (3)
O4B—C1C—H1C	108.9	O2F—C2F—H2F	110.0
O5C—C1C—H1C	108.9	C3F—C2F—H2F	110.0
C2C—C1C—H1C	108.9	C1F—C2F—H2F	110.0
O2C—C2C—C1C	110.7 (3)	C2F—O2F—H2O6	109.5
O2C—C2C—C3C	108.3 (3)	C2F—C3F—C4F	112.3 (3)
C1C—C2C—C3C	109.8 (3)	C2F—C3F—H3F1	109.1
O2C—C2C—H2C	109.3	C4F—C3F—H3F1	109.1
C1C—C2C—H2C	109.3	C2F—C3F—H3F2	109.1
C3C—C2C—H2C	109.3	C4F—C3F—H3F2	109.1
C2C—O2C—H2O3	109.5	H3F1—C3F—H3F2	107.9
C4C—C3C—C2C	111.4 (3)	O4F—C4F—C3F	106.5 (3)
C4C—C3C—H3C1	109.4	O4F—C4F—C5F	108.6 (3)
C2C—C3C—H3C1	109.4	C3F—C4F—C5F	113.0 (3)
C4C—C3C—H3C2	109.4	O4F—C4F—H4F	109.6
C2C—C3C—H3C2	109.4	C3F—C4F—H4F	109.6
H3C1—C3C—H3C2	108.0	C5F—C4F—H4F	109.6
O4C—C4C—C3C	106.1 (3)	O5F—C5F—C6F	104.9 (3)
O4C—C4C—C5C	108.5 (3)	O5F—C5F—C4F	111.5 (3)
C3C—C4C—C5C	112.0 (3)	C6F—C5F—C4F	114.1 (3)
O4C—C4C—H4C	110.1	O5F—C5F—H5F	108.7
C3C—C4C—H4C	110.1	C6F—C5F—H5F	108.7
C5C—C4C—H4C	110.1	C4F—C5F—H5F	108.7
O5C—C5C—C6C	106.5 (3)	C1F—O5F—C5F	114.5 (2)
O5C—C5C—C4C	110.1 (3)	O6F—C6F—C5F	112.7 (3)
C6C—C5C—C4C	113.5 (3)	O6F—C6F—H6F1	109.1
O5C—C5C—H5C	108.9	C5F—C6F—H6F1	109.1
C6C—C5C—H5C	108.9	O6F—C6F—H6F2	109.1
C4C—C5C—H5C	108.9	C5F—C6F—H6F2	109.1
C1C—O5C—C5C	114.0 (3)	H6F1—C6F—H6F2	107.8
O6C—C6C—C5C	113.4 (3)	C6F—O6F—H6O6	109.5
O6C—C6C—H6C1	108.9	H11W—O1W—H12W	106 (3)
C5C—C6C—H6C1	108.9	H21W—O2W—H22W	104 (2)
O6C—C6C—H6C2	108.9	H31W—O3W—H32W	104 (2)
C5C—C6C—H6C2	108.9	H41W—O4W—H42W	107 (3)
H6C1—C6C—H6C2	107.7	H51W—O5W—H52W	110 (3)
C6C—O6C—H6O3	109.5	H61W—O6W—H62W	106 (3)
C1D—O4C—C4C	118.4 (2)	O11L—C11L—C21L	112 (3)
O5D—C1D—O4C	111.5 (3)	C11L—C21L—C31L	92 (2)
O5D—C1D—C2D	111.4 (3)	C41L—C31L—C21L	90.4 (19)
O4C—C1D—C2D	106.9 (3)	O12L—C12L—C22L	99 (3)
O5D—C1D—H1D	109.0	C12L—C22L—C32L	117 (3)
O4C—C1D—H1D	109.0	C42L—C32L—C22L	90.4 (18)

C4F—O4F—C1A—O5A	99.9 (3)	O5D—C1D—C2D—O2D	−59.6 (3)
C4F—O4F—C1A—C2A	−138.3 (3)	O4C—C1D—C2D—O2D	178.3 (2)
O4F—C1A—C2A—O2A	173.4 (3)	O5D—C1D—C2D—C3D	59.5 (3)
O5A—C1A—C2A—O2A	−64.8 (3)	O4C—C1D—C2D—C3D	−62.6 (3)
O4F—C1A—C2A—C3A	−67.1 (4)	O2D—C2D—C3D—C4D	67.4 (4)
O5A—C1A—C2A—C3A	54.7 (4)	C1D—C2D—C3D—C4D	−53.3 (4)
O2A—C2A—C3A—C4A	69.4 (4)	C2D—C3D—C4D—O4D	164.9 (3)
C1A—C2A—C3A—C4A	−50.5 (4)	C2D—C3D—C4D—C5D	46.2 (4)
C2A—C3A—C4A—O4A	165.1 (3)	O4D—C4D—C5D—O5D	−161.7 (2)
C2A—C3A—C4A—C5A	49.0 (4)	C3D—C4D—C5D—O5D	−43.8 (4)
O4A—C4A—C5A—O5A	−168.4 (3)	O4D—C4D—C5D—C6D	79.9 (3)
C3A—C4A—C5A—O5A	−50.6 (4)	C3D—C4D—C5D—C6D	−162.2 (3)
O4A—C4A—C5A—C6A	72.1 (4)	O4C—C1D—O5D—C5D	59.8 (4)
C3A—C4A—C5A—C6A	−170.1 (3)	C2D—C1D—O5D—C5D	−59.5 (3)
O4F—C1A—O5A—C5A	60.4 (4)	C6D—C5D—O5D—C1D	174.1 (3)
C2A—C1A—O5A—C5A	−59.2 (3)	C4D—C5D—O5D—C1D	50.9 (4)
C6A—C5A—O5A—C1A	−179.1 (3)	O5D—C5D—C6D—O6D	−71.1 (4)
C4A—C5A—O5A—C1A	57.1 (4)	C4D—C5D—C6D—O6D	52.2 (4)
O5A—C5A—C6A—O6A	−63.0 (4)	C3D—C4D—O4D—C1E	125.9 (3)
C4A—C5A—C6A—O6A	59.6 (4)	C5D—C4D—O4D—C1E	−112.4 (3)
C5A—C4A—O4A—C1B	−133.5 (3)	C4D—O4D—C1E—O5E	95.1 (3)
C3A—C4A—O4A—C1B	106.7 (3)	C4D—O4D—C1E—C2E	−142.1 (3)
C4A—O4A—C1B—O5B	113.3 (3)	O4D—C1E—C2E—O2E	165.7 (3)
C4A—O4A—C1B—C2B	−124.2 (3)	O5E—C1E—C2E—O2E	−71.5 (3)
O5B—C1B—C2B—O2B	−68.0 (3)	O4D—C1E—C2E—C3E	−70.7 (3)
O4A—C1B—C2B—O2B	170.3 (3)	O5E—C1E—C2E—C3E	52.1 (4)
O5B—C1B—C2B—C3B	54.7 (4)	O2E—C2E—C3E—C4E	71.3 (4)
O4A—C1B—C2B—C3B	−67.0 (4)	C1E—C2E—C3E—C4E	−49.6 (4)
O2B—C2B—C3B—C4B	72.6 (4)	C2E—C3E—C4E—O4E	171.5 (3)
C1B—C2B—C3B—C4B	−49.0 (4)	C2E—C3E—C4E—C5E	51.8 (4)
C2B—C3B—C4B—O4B	166.3 (3)	O4E—C4E—C5E—O5E	−171.2 (2)
C2B—C3B—C4B—C5B	47.6 (4)	C3E—C4E—C5E—O5E	−54.9 (4)
O4B—C4B—C5B—O5B	−164.4 (3)	O4E—C4E—C5E—C6E	70.8 (4)
C3B—C4B—C5B—O5B	−49.3 (4)	C3E—C4E—C5E—C6E	−172.9 (3)
O4B—C4B—C5B—C6B	76.5 (4)	O4D—C1E—O5E—C5E	61.9 (3)
C3B—C4B—C5B—C6B	−168.4 (3)	C2E—C1E—O5E—C5E	−58.7 (4)
O4A—C1B—O5B—C5B	59.5 (4)	C4E—C5E—O5E—C1E	59.8 (3)
C2B—C1B—O5B—C5B	−60.3 (4)	C6E—C5E—O5E—C1E	−175.7 (3)
C6B—C5B—O5B—C1B	−179.0 (3)	O5E—C5E—C6E—O6E	−69.0 (3)
C4B—C5B—O5B—C1B	57.0 (4)	C4E—C5E—C6E—O6E	51.6 (4)
O5B—C5B—C6B—O6B	−65.7 (4)	C5E—C4E—O4E—C1F	−96.5 (3)
C4B—C5B—C6B—O6B	56.4 (4)	C3E—C4E—O4E—C1F	143.6 (3)
C5B—C4B—O4B—C1C	−93.0 (4)	C4E—O4E—C1F—O5F	104.7 (3)
C3B—C4B—O4B—C1C	147.0 (3)	C4E—O4E—C1F—C2F	−133.7 (3)
C4B—O4B—C1C—O5C	111.8 (3)	O5F—C1F—C2F—O2F	−59.3 (4)
C4B—O4B—C1C—C2C	−126.1 (3)	O4E—C1F—C2F—O2F	178.7 (3)
O4B—C1C—C2C—O2C	174.8 (3)	O5F—C1F—C2F—C3F	58.8 (3)
O5C—C1C—C2C—O2C	−62.9 (4)	O4E—C1F—C2F—C3F	−63.3 (3)
O4B—C1C—C2C—C3C	−65.7 (3)	O2F—C2F—C3F—C4F	66.9 (4)
O5C—C1C—C2C—C3C	56.6 (4)	C1F—C2F—C3F—C4F	−52.3 (4)
O2C—C2C—C3C—C4C	69.0 (4)	C1A—O4F—C4F—C3F	130.6 (3)
C1C—C2C—C3C—C4C	−52.0 (4)	C1A—O4F—C4F—C5F	−107.5 (3)
C2C—C3C—C4C—O4C	168.5 (3)	C2F—C3F—C4F—O4F	166.1 (3)
C2C—C3C—C4C—C5C	50.3 (4)	C2F—C3F—C4F—C5F	46.9 (4)
O4C—C4C—C5C—O5C	−167.9 (2)	O4F—C4F—C5F—O5F	−163.5 (3)
C3C—C4C—C5C—O5C	−51.1 (4)	C3F—C4F—C5F—O5F	−45.6 (4)
O4C—C4C—C5C—C6C	72.8 (4)	O4F—C4F—C5F—C6F	77.8 (4)
C3C—C4C—C5C—C6C	−170.5 (3)	C3F—C4F—C5F—C6F	−164.3 (3)
O4B—C1C—O5C—C5C	58.8 (4)	O4E—C1F—O5F—C5F	58.2 (3)
C2C—C1C—O5C—C5C	−60.8 (3)	C2F—C1F—O5F—C5F	−60.9 (3)
C6C—C5C—O5C—C1C	−179.4 (3)	C6F—C5F—O5F—C1F	177.5 (3)
C4C—C5C—O5C—C1C	57.1 (3)	C4F—C5F—O5F—C1F	53.5 (3)
O5C—C5C—C6C—O6C	−74.2 (4)	O5F—C5F—C6F—O6F	−67.8 (4)
C4C—C5C—C6C—O6C	47.1 (4)	C4F—C5F—C6F—O6F	54.6 (4)
C3C—C4C—O4C—C1D	136.9 (3)	O11L—C11L—C21L—C31L	−175 (3)
C5C—C4C—O4C—C1D	−102.6 (3)	C11L—C21L—C31L—C41L	103 (2)
C4C—O4C—C1D—O5D	105.6 (3)	O12L—C12L—C22L—C32L	−115 (3)
C4C—O4C—C1D—C2D	−132.5 (3)	C12L—C22L—C32L—C42L	−151 (3)

Hydrogen-bond geometry (Å, º)

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D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2O1···O6W	0.83	2.05	2.850 (4)	160
O6A—H6O1···O2Cⁱ	0.83	1.90	2.710 (4)	164
O2B—H2O2···O2Wⁱⁱ	0.83	1.95	2.753 (4)	162
O6B—H6O2···O4Wⁱⁱⁱ	0.83	2.09	2.796 (4)	143
O2C—H2O3···O1Wⁱⁱⁱ	0.83	2.05	2.861 (4)	166
O6C—H6O3···O2Aⁱⁱⁱ	0.83	1.87	2.696 (4)	174
O2D—H2O4···O5W^iv	0.83	2.07	2.864 (4)	161
O6D—H6O4···O2F^v	0.83	1.96	2.791 (4)	178
O2E—H2O5···O2B^vi	0.83	1.94	2.705 (4)	152
O6E—H6O5···O6B^vi	0.83	1.88	2.682 (4)	162
O2F—H2O6···O3W	0.83	2.06	2.864 (4)	163
O6F—H6O6···O2D^vii	0.83	1.94	2.770 (3)	174
O1W—H11W···O4W	0.91 (2)	1.93 (2)	2.833 (4)	174 (3)
O1W—H12W···O6F	0.90 (2)	1.82 (2)	2.698 (4)	165 (4)
O2W—H21W···O6A^viii	0.91 (2)	1.79 (2)	2.696 (4)	173 (4)
O2W—H22W···O5W	0.89 (2)	1.89 (2)	2.769 (4)	168 (4)
O3W—H31W···O2W	0.91 (2)	1.93 (2)	2.835 (4)	177 (4)
O3W—H32W···O6C^vii	0.91 (2)	1.88 (2)	2.762 (4)	165 (4)
O4W—H41W···O6W	0.91 (2)	1.98 (2)	2.862 (5)	164 (4)
O4W—H42W···O6D^vii	0.90 (2)	1.90 (2)	2.784 (4)	178 (4)
O5W—H51W···O6E^ix	0.88 (2)	1.87 (2)	2.732 (4)	168 (4)
O5W—H52W···O3W^ix	0.90 (2)	2.13 (2)	2.976 (4)	157 (4)
O6W—H61W···O1W^ix	0.92 (2)	1.90 (2)	2.821 (4)	172 (4)
O6W—H62W···O2E^x	0.89 (2)	1.88 (2)	2.741 (4)	163 (4)

Symmetry codes: (i) −x, y−1/2, −z; (ii) x, y, z−1; (iii) −x, y+1/2, −z; (iv) −x+1, y+1/2, −z+1; (v) −x, y+1/2, −z+1; (vi) x, y, z+1; (vii) −x, y−1/2, −z+1; (viii) x+1, y, z+1; (ix) x+1, y, z; (x) −x+1, y−1/2, −z+1.

Per(3-deoxy)-α-cyclomannin: an n-butanol hexahydrate inclusion complex (2024)

FAQs

What is cyclodextrin inclusion complex? ›

Cyclodextrins have an internal non-polar hole and hydroxyl groups placed on the surface, the inclusion of hydrophobic compounds takes place mainly by hydrophobic interactions between guest molecules and the walls of cyclodextrin cavity [5].

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What is cyclodextrin used for? ›

In nearly every formulation intended for any route, the basic purpose of cyclodextrin is to manage the solubility, increase bioavailability, and increase the solubility. Literature reveals that cyclodextrin is also being used in the development of novel carriers like liposomes, microspheres, nanoparticles, etc.

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How to complex with cyclodextrin? ›

Solvent-Based Methods

Co-precipitation is a simple and cost-effective technique. b. Kneading Method: In this technique, the cyclodextrin and guest molecule are mixed with a small amount of solvent and kneaded to form a viscous mass. The solvent is then evaporated, resulting in the formation of a solid complex.

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What is the application of inclusion complex in pharmacy? ›

The formation of inclusion complexes between drugs and natural or modified cyclodextrins increases aqueous solubility and improves the bioavailability of drugs [23,24,25,26].

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Can cyclodextrin remove plaque from arteries? ›

Conclusions: Targeted removal of 7KC from plaque with proprietary cyclodextrin compounds has the potential to prevent and reverse the formation of atheroscloertic plaques. This innovation represents the first disease-modifying therapeutic approach to treating atherosclerosis.

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Is cyclodextrin safe for humans? ›

Alpha-, beta-, and gamma-cyclodextrin are all generally recognized as safe by the U.S. FDA. They have been applied for delivery of a variety of drugs, including hydrocortisone, prostaglandin, nitroglycerin, itraconazole, chloramphenicol. The cyclodextrin confers solubility and stability to these drugs.

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What is alpha-cyclodextrin good for? ›

The intakes of α-CDs are related to positive physiological effects, such as weight loss, reducing serum triglycerides and leptin levels, improving insulin sensitivity and increasing the volume of fecal fat in rats (Artiss, Brogan, Brucal, Moghaddam, & Jen, 2006).

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What is the disadvantage of cyclodextrin? ›

In spite of these above advantages, cyclodextrin also has some limitations. For example, when β-cyclodextrin interacts with cholesterol it forms a low soluble complex that may have a nephrotoxic impact.

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Do cyclodextrins remove cholesterol? ›

CDs can form inclusion complexes with cholesterol, in which the cholesterol molecule is trapped inside the CD cavity. This complexation results in enhancing the solubility of cholesterol, which can facilitate its removal from the body²^,³^,⁴.

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What are the hazards of cyclodextrin? ›

Eye: May cause eye irritation. Skin: May cause skin irritation. Ingestion: May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.

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How drug is released from cyclodextrin? ›

Dissociation due to dilution appears to be the major release mechanism although other factors such as competitive displacement of the drug from the complex, drug binding to plasma and tissue components, uptake of the drug by tissues not available to the complex or cyclodextrin, and cyclodextrin elimination may also ...

How much beta cyclodextrin should I take? ›

β-Cyclodextrin is a non-reducing cyclic oligosaccharide consisting of seven α-1,4-linked d-glucopyranosyl units. The Scientific Committee on Food (SCF) allocated an acceptable daily intake (ADI) of 5 mg/kg body weight (bw) per day to β-cyclodextrin (E 459) in 1996.

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What are inclusion complexes also known as? ›

In host–guest chemistry, an inclusion compound (also known as an inclusion complex) is a chemical complex in which one chemical compound (the "host") has a cavity into which a "guest" compound can be accommodated.

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What are the advantages of inclusion complexes? ›

Advantages of Cyclodextrin Inclusion Complexation

Reduction of irritation: Drug substances that irritate the stomach, skin or eye can be encapsulated within a CD cavity to reduce their irritancy. Inclusion complexation with CDs reduces the local concentration of the free drug, below the irritancy threshold.

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Why is inclusion complex? ›

Definition: A complex in which one component (the host) forms a cavity or, in the case of a crystal, a crystal lattice containing spaces in the shape of long tunnels or channels in which molecular entities of a second chemical species (the guest) are located.

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What are the advantages of cyclodextrin complex? ›

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What are the disadvantages of cyclodextrin? ›

A key disadvantage of ionic CDs is their inability to form higher order complex, such as 1:2 or 1:3 due to increase in charge density and electrostatic repulsion. Conversely, the neutral charged CDs (HP-β-CD) usually show good complexation with neutral drugs as compared with anionic and cationic drugs.

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What does cyclodextrin do to cholesterol? ›

β-Cyclodextrins decrease cholesterol release and ABC-associated transporter expression in smooth muscle cells and aortic endothelial cells.

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Per(3-deoxy)-α-cyclo­mannin: an n-butanol hexahydrate inclusion complex (2024)

Supporting information

Key indicators

checkCIF results

FAQs

What is cyclodextrin inclusion complex? ›

How drug is released from cyclodextrin? ›

References

Per(3-deoxy)-α-cyclomannin: an n-butanol hexahydrate inclusion complex (2024)