2,2′,3,3′,4,4′-Hexaacetato-6,6′-bis­(isobutanoyl)-α,α-trehalose 0.7-hydrate

In the title compound, C₃₂H₄₆O₁₉·0.7H₂O, all hydroxy groups on the parent compound, trehalose, have been substituted and some disordered bound water is located in the weakly diffracting crystal.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.017 Å
• Disorder in solvent or counterion
• R factor = 0.040
• wR factor = 0.100
• Data-to-parameter ratio = 7.7

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry


 Alert Level A:



DIFF_020  Alert A _diffrn_standards_interval_count and
          _diffrn_standards_interval_time are missing. Number of measurements
          between standards or time (min) between standards.

GOODF_01  Alert A The least squares goodness of fit parameter lies
          outside the range 0.40 <> 6.00
          Goodness of fit given =      0.390

RINTA_01  Alert A The value of Rint is greater than 0.20
          Rint given   0.311


 Alert Level B:



PLAT_213  Alert B Atom  C14    has ADP max/min ratio ...........       4.30


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.00
         From the CIF: _reflns_number_total               3541
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         3779
         Completeness (_total/calc)             93.70%
          Alert C: < 95% complete

PLAT_213  Alert C Atom  C4'    has ADP max/min ratio ...........       3.60

PLAT_213  Alert C Atom  C9'    has ADP max/min ratio ...........       3.60

PLAT_302  Alert C Anion/Solvent disorder .......................      70.00 Perc.

PLAT_420  Alert C D-H without acceptor      >O1'    -  >H1Y               ?

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.00
         From the CIF: _reflns_number_total               3541
         Count of symmetry unique reflns         3779
         Completeness (_total/calc)             93.70%
         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.


 3 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 5 Alert Level C = Please check

---

S1. Comment

Trehalose is a naturally occurring non-reducing disaccharide which is effective in preserving the structural and functional integrity of membranes and proteins from the effects of dehydration (Crowe et al., 1988). Polymorphic, amorphous and crystalline forms of trehalose have been studied (Sussich et al., 1998), and the common crystalline form is the dihydrate (Brown et al., 1972; Taga et al., 1972). The ability of trehalose to readily form hydrates may be related to its support of anhydrobiosis (life without water). We have undertaken a study of substituted trehalose molecules in an attempt to understand the enhanced stabilizing potential of trehalose. In the title compound, (I), all eight hydroxy groups have been substituted, hence removing the possibility of hydrogen-bonding networks with water through these groups.

However, an ill defined water molecule (occupation factor close to 0.7) was found to be incorporated into the crystal lattice. Short distances here are O1'···O5 3.097 (15) Å and O1'···O6'(-1 + x, y, z) 2.965 (13) Å, but uncertainty in location of water H atoms precludes a reliable description of the hydrogen bonding. The substitution at C1,C1' is α,α, with C1—O1 = 1.453 (11) Å, C1'—O1 = 1.435 (11) Å and C1—O1—C1' = 115.5 (8)°. The absolute configuration is R at the carbons C1, C2, C4 and C5 (also at C1', C2', C4' and C5') and S at C3 and C3'. The two six-membered rings adopt chair conformations, with puckering parameters (Cremer & Pople, 1975) calculated with PLATON (Spek, 1998) of Q = 0.56 (1) Å, θ = 9(1)°, ϕ = 94 (7)° (primed atoms) and Q = 0.57 (1) Å, θ = 3(1)° and ϕ = 322 (21)° (unprimed atoms).

S2. Experimental

The title compound, (I), was prepared via the reaction mixture sequence of trehalose and Ph₃CCl followed by addition of CH₃COCl and pyridine, then aqueous hydrobromide was added and finally a mixture of CH₃CH(CH₃)COCl and pyridine was prepared and added. Purification was achieved through a combination of column chromatography and recrystallization. Crystals for X-ray work were obtained by slow evaporation from 95% ethanol.

S3. Refinement

Detailed data collection procedures are described by Darr et al. (1993). The number of intensities with F² > 2σF² was only 16% of the total (565 compared with a total of 3541 unique reflections). Structure solution and refinement with such a weak data led to results that were below the standard normally expected, but are adequate for a qualitative assessment of the structure. With SIR92 (Altomare et al., 1994), the number of atoms in the unit cell was lowered to C₁₀₀H₁₆₈O₇₆ from C₁₂₈H₁₉₂O₈₀ to achieve suitable phasing. All non-H atoms were refined in SHELXL97 with anisotropic displacement parameters and the DELU command which applies rigid bond restraints was used. The H atoms were initially placed in calculated positions and thereafter allowed to ride on their attached atoms. Each H atom was assigned U_iso = 1.2U_eq(C). Water H atoms were not observed on a final difference map but were calculated with CALC-OH (Nardelli, 1999) and the coordinates fixed. Friedel pairs were merged. The absolute configuration is known for trehalose.

Computing details

Data collection: MADNES (Plugrath & Messerschmidt, 1989); cell refinement: MADNES; data reduction: ABSMAD (Karaulov, 1992); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The atomic arrangement in the title molecule. Displacement ellipsoids are shown at the 50% probability level.

6,6'-Di(isobutanoato)-2,2',3,3',4,4'-hexaacetato-α,α-trehalose monohydrate

Crystal data

C32H46O19·0.7H2O	Dx = 1.306 Mg m^−3
Mr = 747.30	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 250 reflections
a = 8.857 (3) Å	θ = 2.0–25.0°
b = 17.813 (11) Å	µ = 0.11 mm^−1
c = 24.085 (3) Å	T = 150 K
V = 3800 (3) Å^3	Lozenge, colourless
Z = 4	0.21 × 0.10 × 0.10 mm
F(000) = 1588

Data collection

Delft Instruments FAST diffractometer	565 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.311
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ϕ and ω scans to fill Ewald sphere	h = −10→8
17076 measured reflections	k = −20→21
3541 independent reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H-atom parameters constrained
S = 0.39	w = 1/[σ^2(Fo^2)]
3541 reflections	(Δ/σ)max < 0.001
460 parameters	Δρmax = 0.19 e Å^−3
117 restraints	Δρmin = −0.17 e Å^−3

Special details

Experimental. Absence of crystal decay in the X-ray beam was confirmed by checking equivalent reflections at the beginning and end of data collection which lasted about 8 h.

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

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.4189 (8)	0.3059 (3)	0.7560 (3)	0.026 (2)
O2	0.5742 (9)	0.4212 (4)	0.7104 (3)	0.032 (2)
O3	0.4644 (10)	0.4986 (4)	0.6507 (3)	0.042 (2)
O4	0.6376 (8)	0.5013 (4)	0.8068 (3)	0.030 (2)
O5	0.2354 (8)	0.3861 (3)	0.7954 (3)	0.0248 (19)
O6	0.8311 (10)	0.4333 (4)	0.8381 (5)	0.080 (4)
O7	0.5029 (8)	0.4290 (4)	0.9058 (3)	0.031 (2)
O8	0.5508 (9)	0.5522 (4)	0.9200 (3)	0.041 (3)
O9	0.0997 (9)	0.3177 (4)	0.8882 (3)	0.035 (2)
O10	−0.0285 (10)	0.3525 (4)	0.9646 (4)	0.056 (3)
O2'	0.4598 (9)	0.1780 (4)	0.8145 (3)	0.029 (2)
O3'	0.2429 (10)	0.1122 (4)	0.8257 (4)	0.047 (3)
O4'	0.6793 (9)	0.1174 (3)	0.7449 (3)	0.029 (2)
O5'	0.3244 (9)	0.2391 (4)	0.6784 (3)	0.026 (2)
O6'	0.8955 (9)	0.1835 (4)	0.7547 (4)	0.058 (3)
O7'	0.7209 (9)	0.2174 (3)	0.6448 (3)	0.030 (2)
O8'	0.7985 (9)	0.1018 (3)	0.6215 (3)	0.041 (3)
O9'	0.3610 (9)	0.3200 (4)	0.5776 (3)	0.036 (2)
O10'	0.2358 (10)	0.2692 (4)	0.5055 (3)	0.048 (3)
O1'	−0.0418 (15)	0.3417 (6)	0.7242 (5)	0.066 (6)	0.702 (12)
H1X	0.0253	0.3559	0.7490	0.079*	0.702 (12)
H1Y	0.0100	0.3124	0.7022	0.079*	0.702 (12)
C1	0.3364 (13)	0.3761 (5)	0.7511 (5)	0.026 (3)
H1	0.2809	0.3778	0.7150	0.031*
C2	0.4566 (13)	0.4354 (6)	0.7523 (5)	0.026 (3)
H2	0.4099	0.4856	0.7455	0.031*
C3	0.5382 (13)	0.4364 (5)	0.8060 (5)	0.022 (2)
H3	0.5990	0.3894	0.8100	0.026*
C4	0.4271 (13)	0.4428 (6)	0.8537 (5)	0.026 (3)
H4	0.3783	0.4934	0.8538	0.031*
C5	0.3076 (13)	0.3808 (5)	0.8493 (5)	0.021 (3)
H5	0.3570	0.3306	0.8532	0.025*
C6	0.5636 (17)	0.4535 (6)	0.6620 (6)	0.042 (4)
C7	0.6969 (13)	0.4354 (6)	0.6245 (5)	0.045 (4)
H7A	0.7625	0.3988	0.6429	0.054*
H7B	0.7540	0.4814	0.6170	0.054*
H7C	0.6599	0.4143	0.5895	0.054*
C8	0.7821 (14)	0.4909 (6)	0.8247 (6)	0.042 (4)
C9	0.8616 (13)	0.5644 (6)	0.8239 (5)	0.055 (5)
H9A	0.7927	0.6035	0.8105	0.066*
H9B	0.9493	0.5614	0.7992	0.066*
H9C	0.8953	0.5769	0.8616	0.066*
C10	0.5614 (15)	0.4869 (6)	0.9346 (5)	0.035 (3)
C11	0.6601 (15)	0.4620 (6)	0.9841 (5)	0.062 (5)
H11A	0.6513	0.4076	0.9891	0.075*
H11B	0.6260	0.4876	1.0179	0.075*
H11C	0.7657	0.4751	0.9768	0.075*
C12	0.1790 (13)	0.3868 (5)	0.8896 (5)	0.027 (3)
H12A	0.2176	0.3966	0.9274	0.032*
H12B	0.1111	0.4285	0.8788	0.032*
C13	−0.0123 (15)	0.3094 (7)	0.9273 (6)	0.038 (3)
C14	−0.0968 (15)	0.2346 (6)	0.9176 (5)	0.044 (4)
H14	−0.0277	0.1981	0.8989	0.053*
C15	−0.2293 (15)	0.2534 (7)	0.8784 (6)	0.089 (6)
H15A	−0.2862	0.2075	0.8702	0.107*
H15B	−0.1899	0.2746	0.8438	0.107*
H15C	−0.2961	0.2900	0.8964	0.107*
C16	−0.1536 (17)	0.2010 (7)	0.9712 (6)	0.098 (6)
H16A	−0.2058	0.1537	0.9633	0.117*
H16B	−0.2237	0.2361	0.9890	0.117*
H16C	−0.0680	0.1915	0.9960	0.117*
C1'	0.3408 (13)	0.2404 (5)	0.7365 (5)	0.025 (3)
H1'	0.2392	0.2373	0.7545	0.030*
C2'	0.4374 (13)	0.1753 (5)	0.7556 (5)	0.027 (3)
H2'	0.3916	0.1264	0.7442	0.033*
C3'	0.5955 (13)	0.1843 (6)	0.7309 (5)	0.024 (3)
H3'	0.6463	0.2299	0.7463	0.028*
C4'	0.5822 (13)	0.1895 (5)	0.6679 (5)	0.020 (3)
H4'	0.5579	0.1392	0.6519	0.024*
C5'	0.4663 (12)	0.2474 (6)	0.6488 (5)	0.026 (3)
H5'	0.5074	0.2983	0.6577	0.032*
C6'	0.3475 (17)	0.1429 (7)	0.8456 (6)	0.042 (4)
C7'	0.3829 (13)	0.1495 (5)	0.9056 (4)	0.043 (4)
H7'A	0.4749	0.1793	0.9104	0.051*
H7'B	0.3982	0.0994	0.9213	0.051*
H7'C	0.2988	0.1742	0.9247	0.051*
C8'	0.8263 (15)	0.1254 (6)	0.7613 (5)	0.035 (3)*
C9'	0.8852 (13)	0.0548 (6)	0.7870 (5)	0.061 (5)
H9'A	0.8046	0.0171	0.7881	0.073*
H9'B	0.9199	0.0653	0.8248	0.073*
H9'C	0.9696	0.0357	0.7648	0.073*
C10'	0.8236 (16)	0.1684 (6)	0.6204 (5)	0.042 (4)*
C11'	0.9575 (12)	0.2092 (5)	0.5993 (5)	0.044 (4)
H11X	0.9444	0.2632	0.6055	0.053*
H11Y	0.9689	0.1996	0.5594	0.053*
H11Z	1.0479	0.1918	0.6189	0.053*
C12'	0.4292 (12)	0.2462 (5)	0.5882 (4)	0.030 (3)
H12X	0.5216	0.2392	0.5656	0.035*
H12Y	0.3572	0.2053	0.5795	0.035*
C13'	0.2639 (15)	0.3212 (6)	0.5350 (5)	0.034 (3)
C14'	0.1955 (17)	0.4013 (6)	0.5286 (6)	0.056 (4)
H14X	0.1186	0.4000	0.4982	0.068*
C15'	0.3105 (17)	0.4588 (6)	0.5145 (5)	0.093 (6)
H15X	0.2617	0.5080	0.5110	0.112*
H15Y	0.3588	0.4456	0.4792	0.112*
H15Z	0.3869	0.4608	0.5439	0.112*
C16'	0.1135 (17)	0.4223 (6)	0.5842 (6)	0.104 (7)
H16X	0.0327	0.3860	0.5914	0.125*
H16Y	0.0703	0.4728	0.5810	0.125*
H16Z	0.1863	0.4212	0.6148	0.125*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.024 (6)	0.022 (3)	0.030 (5)	0.008 (4)	−0.003 (4)	−0.002 (4)
O2	0.038 (6)	0.029 (4)	0.029 (5)	0.006 (4)	0.010 (4)	0.009 (4)
O3	0.054 (7)	0.048 (5)	0.022 (5)	0.012 (5)	0.002 (5)	0.002 (5)
O4	0.023 (5)	0.026 (4)	0.041 (6)	−0.001 (4)	−0.002 (4)	−0.005 (4)
O5	0.022 (6)	0.023 (4)	0.030 (5)	0.007 (4)	0.000 (4)	0.004 (4)
O6	0.050 (8)	0.039 (5)	0.152 (11)	−0.005 (5)	−0.034 (7)	0.046 (6)
O7	0.039 (7)	0.028 (4)	0.026 (5)	0.002 (4)	−0.010 (4)	−0.003 (4)
O8	0.054 (7)	0.035 (4)	0.035 (6)	0.002 (5)	−0.016 (5)	−0.008 (5)
O9	0.040 (7)	0.037 (4)	0.029 (6)	−0.013 (4)	0.011 (4)	−0.012 (4)
O10	0.064 (8)	0.072 (6)	0.033 (6)	−0.021 (5)	0.026 (5)	−0.012 (5)
O2'	0.035 (6)	0.027 (4)	0.025 (5)	0.005 (4)	0.000 (4)	−0.006 (4)
O3'	0.037 (7)	0.047 (5)	0.056 (7)	−0.007 (5)	−0.008 (5)	0.016 (5)
O4'	0.025 (5)	0.017 (4)	0.045 (6)	0.005 (4)	−0.006 (5)	0.006 (4)
O5'	0.023 (5)	0.031 (4)	0.023 (5)	0.011 (4)	−0.006 (4)	0.004 (4)
O6'	0.029 (7)	0.037 (5)	0.106 (9)	−0.010 (5)	−0.026 (6)	0.015 (6)
O7'	0.029 (6)	0.027 (4)	0.034 (6)	−0.001 (4)	0.006 (4)	0.000 (4)
O8'	0.040 (7)	0.033 (4)	0.049 (7)	0.000 (4)	0.002 (5)	0.004 (4)
O9'	0.046 (7)	0.033 (4)	0.028 (6)	0.000 (4)	−0.020 (4)	0.000 (4)
O10'	0.057 (8)	0.056 (5)	0.031 (6)	0.002 (5)	−0.025 (5)	−0.004 (5)
O1'	0.062 (13)	0.060 (9)	0.076 (12)	0.017 (8)	0.002 (8)	−0.009 (8)
C1	0.036 (8)	0.017 (5)	0.025 (7)	0.002 (5)	0.003 (5)	0.007 (6)
C2	0.025 (8)	0.021 (5)	0.032 (6)	0.003 (5)	−0.002 (5)	−0.008 (6)
C3	0.017 (7)	0.019 (5)	0.029 (5)	0.006 (5)	−0.002 (5)	0.004 (6)
C4	0.029 (8)	0.022 (6)	0.026 (6)	0.005 (5)	−0.003 (5)	−0.003 (6)
C5	0.019 (7)	0.016 (5)	0.028 (6)	0.004 (5)	−0.002 (5)	0.006 (6)
C6	0.060 (11)	0.026 (7)	0.039 (8)	−0.001 (7)	0.020 (8)	−0.004 (6)
C7	0.039 (10)	0.045 (7)	0.052 (9)	−0.012 (7)	0.027 (7)	−0.005 (8)
C8	0.025 (8)	0.026 (6)	0.075 (12)	−0.011 (6)	−0.004 (8)	0.009 (8)
C9	0.041 (10)	0.034 (6)	0.089 (13)	−0.024 (7)	0.009 (8)	−0.009 (8)
C10	0.028 (10)	0.052 (7)	0.026 (8)	0.003 (8)	−0.001 (6)	−0.009 (6)
C11	0.078 (14)	0.079 (9)	0.029 (9)	0.008 (9)	−0.034 (7)	−0.006 (8)
C12	0.030 (8)	0.017 (5)	0.034 (7)	−0.007 (5)	0.000 (6)	−0.017 (6)
C13	0.035 (9)	0.052 (8)	0.025 (9)	−0.002 (6)	0.005 (6)	0.007 (6)
C14	0.038 (10)	0.057 (8)	0.038 (9)	−0.016 (7)	0.032 (7)	−0.003 (7)
C15	0.102 (16)	0.068 (9)	0.097 (13)	−0.051 (10)	−0.042 (11)	0.014 (10)
C16	0.111 (17)	0.115 (12)	0.068 (12)	−0.059 (11)	0.009 (10)	0.043 (10)
C1'	0.029 (8)	0.014 (5)	0.031 (6)	0.002 (5)	0.005 (6)	0.002 (6)
C2'	0.039 (8)	0.020 (5)	0.024 (6)	0.014 (6)	−0.008 (5)	−0.011 (5)
C3'	0.017 (7)	0.015 (6)	0.038 (6)	−0.001 (5)	−0.009 (5)	0.002 (6)
C4'	0.020 (7)	0.007 (5)	0.034 (6)	0.008 (5)	−0.007 (5)	0.000 (5)
C5'	0.018 (7)	0.030 (6)	0.031 (6)	0.009 (6)	−0.003 (5)	0.000 (6)
C6'	0.039 (11)	0.051 (9)	0.037 (7)	0.003 (7)	0.000 (7)	0.004 (8)
C7'	0.058 (12)	0.038 (7)	0.033 (7)	0.014 (7)	0.006 (7)	−0.001 (7)
C9'	0.064 (12)	0.044 (7)	0.074 (13)	0.012 (8)	−0.041 (9)	0.025 (8)
C11'	0.026 (9)	0.058 (8)	0.048 (10)	0.007 (6)	0.011 (7)	0.029 (8)
C12'	0.035 (9)	0.027 (6)	0.026 (6)	0.010 (6)	0.001 (6)	0.004 (6)
C13'	0.039 (10)	0.046 (6)	0.018 (8)	0.007 (7)	−0.005 (6)	0.010 (6)
C14'	0.074 (13)	0.049 (7)	0.047 (10)	0.025 (7)	−0.012 (8)	0.021 (7)
C15'	0.19 (2)	0.047 (7)	0.045 (12)	−0.020 (9)	0.006 (11)	−0.002 (9)
C16'	0.152 (19)	0.068 (10)	0.092 (15)	0.046 (10)	0.035 (12)	0.013 (11)

Geometric parameters (Å, º)

O1—C1'	1.435 (11)	O8'—C10'	1.207 (11)
O1—C1	1.453 (11)	O9'—C13'	1.339 (13)
O2—C6	1.302 (14)	O9'—C12'	1.470 (10)
O2—C2	1.473 (12)	O10'—C13'	1.194 (12)
O3—C6	1.221 (14)	C1—C2	1.500 (13)
O4—C8	1.363 (13)	C2—C3	1.480 (14)
O4—C3	1.452 (11)	C3—C4	1.518 (14)
O5—C1	1.404 (12)	C4—C5	1.533 (14)
O5—C5	1.451 (12)	C5—C12	1.499 (14)
O6—C8	1.159 (12)	C6—C7	1.521 (15)
O7—C10	1.347 (12)	C8—C9	1.488 (14)
O7—C4	1.445 (13)	C10—C11	1.543 (15)
O8—C10	1.220 (12)	C13—C14	1.546 (15)
O9—C13	1.375 (13)	C14—C16	1.508 (15)
O9—C12	1.418 (11)	C14—C15	1.543 (16)
O10—C13	1.191 (13)	C1'—C2'	1.511 (13)
O2'—C6'	1.392 (14)	C2'—C3'	1.530 (14)
O2'—C2'	1.435 (12)	C3'—C4'	1.525 (14)
O3'—C6'	1.177 (14)	C4'—C5'	1.526 (13)
O4'—C8'	1.368 (13)	C5'—C12'	1.496 (14)
O4'—C3'	1.444 (11)	C6'—C7'	1.482 (15)
O5'—C1'	1.407 (12)	C8'—C9'	1.496 (14)
O5'—C5'	1.453 (12)	C10'—C11'	1.481 (14)
O6'—C8'	1.213 (12)	C13'—C14'	1.558 (15)
O7'—C10'	1.390 (14)	C14'—C15'	1.484 (15)
O7'—C4'	1.438 (12)	C14'—C16'	1.567 (16)
C1'—O1—C1	115.5 (8)	O10—C13—C14	127.7 (12)
C6—O2—C2	119.1 (10)	O9—C13—C14	109.8 (11)
C8—O4—C3	117.7 (9)	C16—C14—C15	110.9 (12)
C1—O5—C5	113.0 (9)	C16—C14—C13	111.9 (11)
C10—O7—C4	119.8 (8)	C15—C14—C13	105.9 (10)
C13—O9—C12	115.8 (9)	O5'—C1'—O1	112.8 (9)
C6'—O2'—C2'	114.7 (10)	O5'—C1'—C2'	110.3 (9)
C8'—O4'—C3'	118.0 (9)	O1—C1'—C2'	104.6 (9)
C1'—O5'—C5'	113.5 (9)	O2'—C2'—C1'	110.6 (9)
C10'—O7'—C4'	120.4 (8)	O2'—C2'—C3'	104.8 (9)
C13'—O9'—C12'	114.3 (9)	C1'—C2'—C3'	108.7 (9)
O5—C1—O1	111.6 (8)	O4'—C3'—C4'	108.9 (9)
O5—C1—C2	110.3 (9)	O4'—C3'—C2'	107.1 (8)
O1—C1—C2	104.3 (9)	C4'—C3'—C2'	108.8 (10)
O2—C2—C3	104.8 (9)	O7'—C4'—C3'	109.9 (10)
O2—C2—C1	111.6 (9)	O7'—C4'—C5'	103.0 (8)
C3—C2—C1	111.9 (10)	C3'—C4'—C5'	113.2 (9)
O4—C3—C2	108.6 (9)	O5'—C5'—C12'	106.8 (9)
O4—C3—C4	108.8 (9)	O5'—C5'—C4'	111.4 (9)
C2—C3—C4	110.2 (10)	C12'—C5'—C4'	115.6 (9)
O7—C4—C3	110.1 (10)	O3'—C6'—O2'	123.5 (14)
O7—C4—C5	105.0 (9)	O3'—C6'—C7'	126.8 (14)
C3—C4—C5	110.0 (9)	O2'—C6'—C7'	109.7 (12)
O5—C5—C12	103.9 (10)	O6'—C8'—O4'	122.2 (11)
O5—C5—C4	108.6 (8)	O6'—C8'—C9'	126.6 (13)
C12—C5—C4	115.4 (9)	O4'—C8'—C9'	111.3 (11)
O3—C6—O2	122.9 (13)	O8'—C10'—O7'	119.2 (12)
O3—C6—C7	124.4 (13)	O8'—C10'—C11'	129.6 (13)
O2—C6—C7	112.4 (12)	O7'—C10'—C11'	111.1 (10)
O6—C8—O4	124.0 (12)	O9'—C12'—C5'	104.3 (8)
O6—C8—C9	127.2 (13)	O10'—C13'—O9'	125.3 (11)
O4—C8—C9	108.8 (10)	O10'—C13'—C14'	124.8 (12)
O8—C10—O7	123.4 (11)	O9'—C13'—C14'	109.9 (11)
O8—C10—C11	122.7 (11)	C15'—C14'—C13'	112.8 (12)
O7—C10—C11	113.4 (10)	C15'—C14'—C16'	110.5 (11)
O9—C12—C5	107.5 (8)	C13'—C14'—C16'	108.3 (11)
O10—C13—O9	122.3 (11)
C5—O5—C1—O1	54.7 (11)	C5'—O5'—C1'—O1	54.3 (11)
C5—O5—C1—C2	−60.8 (11)	C5'—O5'—C1'—C2'	−62.2 (12)
C1'—O1—C1—O5	82.2 (12)	C1—O1—C1'—O5'	69.9 (12)
C1'—O1—C1—C2	−158.7 (9)	C1—O1—C1'—C2'	−170.1 (9)
C6—O2—C2—C3	−144.2 (10)	C6'—O2'—C2'—C1'	87.0 (12)
C6—O2—C2—C1	94.5 (12)	C6'—O2'—C2'—C3'	−156.0 (9)
O5—C1—C2—O2	173.3 (9)	O5'—C1'—C2'—O2'	177.6 (9)
O1—C1—C2—O2	53.3 (12)	O1—C1'—C2'—O2'	56.1 (12)
O5—C1—C2—C3	56.3 (13)	O5'—C1'—C2'—C3'	63.1 (12)
O1—C1—C2—C3	−63.8 (12)	O1—C1'—C2'—C3'	−58.4 (11)
C8—O4—C3—C2	−134.1 (11)	C8'—O4'—C3'—C4'	104.0 (12)
C8—O4—C3—C4	105.9 (12)	C8'—O4'—C3'—C2'	−138.6 (10)
O2—C2—C3—O4	66.6 (10)	O2'—C2'—C3'—O4'	67.8 (10)
C1—C2—C3—O4	−172.3 (9)	C1'—C2'—C3'—O4'	−173.9 (8)
O2—C2—C3—C4	−174.3 (8)	O2'—C2'—C3'—C4'	−174.7 (7)
C1—C2—C3—C4	−53.2 (12)	C1'—C2'—C3'—C4'	−56.4 (11)
C10—O7—C4—C3	92.0 (12)	C10'—O7'—C4'—C3'	101.3 (11)
C10—O7—C4—C5	−149.7 (10)	C10'—O7'—C4'—C5'	−137.8 (10)
O4—C3—C4—O7	−72.4 (10)	O4'—C3'—C4'—O7'	−78.7 (10)
C2—C3—C4—O7	168.7 (8)	C2'—C3'—C4'—O7'	164.9 (7)
O4—C3—C4—C5	172.5 (8)	O4'—C3'—C4'—C5'	166.7 (9)
C2—C3—C4—C5	53.5 (12)	C2'—C3'—C4'—C5'	50.4 (12)
C1—O5—C5—C12	−175.5 (7)	C1'—O5'—C5'—C12'	−179.1 (8)
C1—O5—C5—C4	61.1 (11)	C1'—O5'—C5'—C4'	53.8 (11)
O7—C4—C5—O5	−174.5 (8)	O7'—C4'—C5'—O5'	−166.7 (8)
C3—C4—C5—O5	−56.1 (12)	C3'—C4'—C5'—O5'	−48.0 (13)
O7—C4—C5—C12	69.4 (12)	O7'—C4'—C5'—C12'	71.2 (12)
C3—C4—C5—C12	−172.2 (10)	C3'—C4'—C5'—C12'	−170.1 (10)
C2—O2—C6—O3	4.1 (19)	C2'—O2'—C6'—O3'	1.0 (18)
C2—O2—C6—C7	177.8 (9)	C2'—O2'—C6'—C7'	−179.9 (9)
C3—O4—C8—O6	2 (2)	C3'—O4'—C8'—O6'	−13.8 (18)
C3—O4—C8—C9	−178.1 (10)	C3'—O4'—C8'—C9'	166.4 (9)
C4—O7—C10—O8	2.0 (19)	C4'—O7'—C10'—O8'	−3.8 (18)
C4—O7—C10—C11	−170.8 (11)	C4'—O7'—C10'—C11'	179.8 (9)
C13—O9—C12—C5	172.8 (10)	C13'—O9'—C12'—C5'	−152.9 (10)
O5—C5—C12—O9	74.1 (10)	O5'—C5'—C12'—O9'	74.4 (10)
C4—C5—C12—O9	−167.2 (9)	C4'—C5'—C12'—O9'	−161.1 (9)
C12—O9—C13—O10	−9.9 (19)	C12'—O9'—C13'—O10'	−3.0 (19)
C12—O9—C13—C14	175.3 (10)	C12'—O9'—C13'—C14'	178.5 (10)
O10—C13—C14—C16	−26 (2)	O10'—C13'—C14'—C15'	−115.0 (15)
O9—C13—C14—C16	148.2 (11)	O9'—C13'—C14'—C15'	63.6 (15)
O10—C13—C14—C15	94.7 (17)	O10'—C13'—C14'—C16'	122.4 (15)
O9—C13—C14—C15	−90.9 (13)	O9'—C13'—C14'—C16'	−59.1 (15)