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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800020705/cf6028sup1.cif
Contains datablocks treh1e, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800020705/cf6028Isup2.hkl
Contains datablock I

CCDC reference: 155897

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
Red Alert 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
Amber Alert Alert Level B:
PLAT_213 Alert B Atom C14 has ADP max/min ratio ........... 4.30
Yellow Alert 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

Comment top

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).

Experimental top

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.

Refinement top

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 Uiso = 1.2Ueq(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 top

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 top
[Figure 1] 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 top
Crystal data top
C32H46O19·0.7H2ODx = 1.306 Mg m3
Mr = 747.30Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 250 reflections
a = 8.857 (3) Åθ = 2.0–25.0°
b = 17.813 (11) ŵ = 0.11 mm1
c = 24.085 (3) ÅT = 150 K
V = 3800 (3) Å3Lozenge, colourless
Z = 40.21 × 0.10 × 0.10 mm
F(000) = 1588
Data collection top
Delft Instruments FAST
diffractometer
565 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.311
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
ϕ and ω scans to fill Ewald sphereh = 108
17076 measured reflectionsk = 2021
3541 independent reflectionsl = 2727
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 0.39 w = 1/[σ2(Fo2)]
3541 reflections(Δ/σ)max < 0.001
460 parametersΔρmax = 0.19 e Å3
117 restraintsΔρmin = 0.17 e Å3
Crystal data top
C32H46O19·0.7H2OV = 3800 (3) Å3
Mr = 747.30Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.857 (3) ŵ = 0.11 mm1
b = 17.813 (11) ÅT = 150 K
c = 24.085 (3) Å0.21 × 0.10 × 0.10 mm
Data collection top
Delft Instruments FAST
diffractometer
565 reflections with I > 2σ(I)
17076 measured reflectionsRint = 0.311
3541 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040117 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 0.39Δρmax = 0.19 e Å3
3541 reflectionsΔρmin = 0.17 e Å3
460 parameters
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.4189 (8)0.3059 (3)0.7560 (3)0.026 (2)
O20.5742 (9)0.4212 (4)0.7104 (3)0.032 (2)
O30.4644 (10)0.4986 (4)0.6507 (3)0.042 (2)
O40.6376 (8)0.5013 (4)0.8068 (3)0.030 (2)
O50.2354 (8)0.3861 (3)0.7954 (3)0.0248 (19)
O60.8311 (10)0.4333 (4)0.8381 (5)0.080 (4)
O70.5029 (8)0.4290 (4)0.9058 (3)0.031 (2)
O80.5508 (9)0.5522 (4)0.9200 (3)0.041 (3)
O90.0997 (9)0.3177 (4)0.8882 (3)0.035 (2)
O100.0285 (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)
H1X0.02530.35590.74900.079*0.702 (12)
H1Y0.01000.31240.70220.079*0.702 (12)
C10.3364 (13)0.3761 (5)0.7511 (5)0.026 (3)
H10.28090.37780.71500.031*
C20.4566 (13)0.4354 (6)0.7523 (5)0.026 (3)
H20.40990.48560.74550.031*
C30.5382 (13)0.4364 (5)0.8060 (5)0.022 (2)
H30.59900.38940.81000.026*
C40.4271 (13)0.4428 (6)0.8537 (5)0.026 (3)
H40.37830.49340.85380.031*
C50.3076 (13)0.3808 (5)0.8493 (5)0.021 (3)
H50.35700.33060.85320.025*
C60.5636 (17)0.4535 (6)0.6620 (6)0.042 (4)
C70.6969 (13)0.4354 (6)0.6245 (5)0.045 (4)
H7A0.76250.39880.64290.054*
H7B0.75400.48140.61700.054*
H7C0.65990.41430.58950.054*
C80.7821 (14)0.4909 (6)0.8247 (6)0.042 (4)
C90.8616 (13)0.5644 (6)0.8239 (5)0.055 (5)
H9A0.79270.60350.81050.066*
H9B0.94930.56140.79920.066*
H9C0.89530.57690.86160.066*
C100.5614 (15)0.4869 (6)0.9346 (5)0.035 (3)
C110.6601 (15)0.4620 (6)0.9841 (5)0.062 (5)
H11A0.65130.40760.98910.075*
H11B0.62600.48761.01790.075*
H11C0.76570.47510.97680.075*
C120.1790 (13)0.3868 (5)0.8896 (5)0.027 (3)
H12A0.21760.39660.92740.032*
H12B0.11110.42850.87880.032*
C130.0123 (15)0.3094 (7)0.9273 (6)0.038 (3)
C140.0968 (15)0.2346 (6)0.9176 (5)0.044 (4)
H140.02770.19810.89890.053*
C150.2293 (15)0.2534 (7)0.8784 (6)0.089 (6)
H15A0.28620.20750.87020.107*
H15B0.18990.27460.84380.107*
H15C0.29610.29000.89640.107*
C160.1536 (17)0.2010 (7)0.9712 (6)0.098 (6)
H16A0.20580.15370.96330.117*
H16B0.22370.23610.98900.117*
H16C0.06800.19150.99600.117*
C1'0.3408 (13)0.2404 (5)0.7365 (5)0.025 (3)
H1'0.23920.23730.75450.030*
C2'0.4374 (13)0.1753 (5)0.7556 (5)0.027 (3)
H2'0.39160.12640.74420.033*
C3'0.5955 (13)0.1843 (6)0.7309 (5)0.024 (3)
H3'0.64630.22990.74630.028*
C4'0.5822 (13)0.1895 (5)0.6679 (5)0.020 (3)
H4'0.55790.13920.65190.024*
C5'0.4663 (12)0.2474 (6)0.6488 (5)0.026 (3)
H5'0.50740.29830.65770.032*
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'A0.47490.17930.91040.051*
H7'B0.39820.09940.92130.051*
H7'C0.29880.17420.92470.051*
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'A0.80460.01710.78810.073*
H9'B0.91990.06530.82480.073*
H9'C0.96960.03570.76480.073*
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)
H11X0.94440.26320.60550.053*
H11Y0.96890.19960.55940.053*
H11Z1.04790.19180.61890.053*
C12'0.4292 (12)0.2462 (5)0.5882 (4)0.030 (3)
H12X0.52160.23920.56560.035*
H12Y0.35720.20530.57950.035*
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)
H14X0.11860.40000.49820.068*
C15'0.3105 (17)0.4588 (6)0.5145 (5)0.093 (6)
H15X0.26170.50800.51100.112*
H15Y0.35880.44560.47920.112*
H15Z0.38690.46080.54390.112*
C16'0.1135 (17)0.4223 (6)0.5842 (6)0.104 (7)
H16X0.03270.38600.59140.125*
H16Y0.07030.47280.58100.125*
H16Z0.18630.42120.61480.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.024 (6)0.022 (3)0.030 (5)0.008 (4)0.003 (4)0.002 (4)
O20.038 (6)0.029 (4)0.029 (5)0.006 (4)0.010 (4)0.009 (4)
O30.054 (7)0.048 (5)0.022 (5)0.012 (5)0.002 (5)0.002 (5)
O40.023 (5)0.026 (4)0.041 (6)0.001 (4)0.002 (4)0.005 (4)
O50.022 (6)0.023 (4)0.030 (5)0.007 (4)0.000 (4)0.004 (4)
O60.050 (8)0.039 (5)0.152 (11)0.005 (5)0.034 (7)0.046 (6)
O70.039 (7)0.028 (4)0.026 (5)0.002 (4)0.010 (4)0.003 (4)
O80.054 (7)0.035 (4)0.035 (6)0.002 (5)0.016 (5)0.008 (5)
O90.040 (7)0.037 (4)0.029 (6)0.013 (4)0.011 (4)0.012 (4)
O100.064 (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)
C10.036 (8)0.017 (5)0.025 (7)0.002 (5)0.003 (5)0.007 (6)
C20.025 (8)0.021 (5)0.032 (6)0.003 (5)0.002 (5)0.008 (6)
C30.017 (7)0.019 (5)0.029 (5)0.006 (5)0.002 (5)0.004 (6)
C40.029 (8)0.022 (6)0.026 (6)0.005 (5)0.003 (5)0.003 (6)
C50.019 (7)0.016 (5)0.028 (6)0.004 (5)0.002 (5)0.006 (6)
C60.060 (11)0.026 (7)0.039 (8)0.001 (7)0.020 (8)0.004 (6)
C70.039 (10)0.045 (7)0.052 (9)0.012 (7)0.027 (7)0.005 (8)
C80.025 (8)0.026 (6)0.075 (12)0.011 (6)0.004 (8)0.009 (8)
C90.041 (10)0.034 (6)0.089 (13)0.024 (7)0.009 (8)0.009 (8)
C100.028 (10)0.052 (7)0.026 (8)0.003 (8)0.001 (6)0.009 (6)
C110.078 (14)0.079 (9)0.029 (9)0.008 (9)0.034 (7)0.006 (8)
C120.030 (8)0.017 (5)0.034 (7)0.007 (5)0.000 (6)0.017 (6)
C130.035 (9)0.052 (8)0.025 (9)0.002 (6)0.005 (6)0.007 (6)
C140.038 (10)0.057 (8)0.038 (9)0.016 (7)0.032 (7)0.003 (7)
C150.102 (16)0.068 (9)0.097 (13)0.051 (10)0.042 (11)0.014 (10)
C160.111 (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) top
O1—C1'1.435 (11)O8'—C10'1.207 (11)
O1—C11.453 (11)O9'—C13'1.339 (13)
O2—C61.302 (14)O9'—C12'1.470 (10)
O2—C21.473 (12)O10'—C13'1.194 (12)
O3—C61.221 (14)C1—C21.500 (13)
O4—C81.363 (13)C2—C31.480 (14)
O4—C31.452 (11)C3—C41.518 (14)
O5—C11.404 (12)C4—C51.533 (14)
O5—C51.451 (12)C5—C121.499 (14)
O6—C81.159 (12)C6—C71.521 (15)
O7—C101.347 (12)C8—C91.488 (14)
O7—C41.445 (13)C10—C111.543 (15)
O8—C101.220 (12)C13—C141.546 (15)
O9—C131.375 (13)C14—C161.508 (15)
O9—C121.418 (11)C14—C151.543 (16)
O10—C131.191 (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—C1115.5 (8)O10—C13—C14127.7 (12)
C6—O2—C2119.1 (10)O9—C13—C14109.8 (11)
C8—O4—C3117.7 (9)C16—C14—C15110.9 (12)
C1—O5—C5113.0 (9)C16—C14—C13111.9 (11)
C10—O7—C4119.8 (8)C15—C14—C13105.9 (10)
C13—O9—C12115.8 (9)O5'—C1'—O1112.8 (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—O1111.6 (8)O4'—C3'—C4'108.9 (9)
O5—C1—C2110.3 (9)O4'—C3'—C2'107.1 (8)
O1—C1—C2104.3 (9)C4'—C3'—C2'108.8 (10)
O2—C2—C3104.8 (9)O7'—C4'—C3'109.9 (10)
O2—C2—C1111.6 (9)O7'—C4'—C5'103.0 (8)
C3—C2—C1111.9 (10)C3'—C4'—C5'113.2 (9)
O4—C3—C2108.6 (9)O5'—C5'—C12'106.8 (9)
O4—C3—C4108.8 (9)O5'—C5'—C4'111.4 (9)
C2—C3—C4110.2 (10)C12'—C5'—C4'115.6 (9)
O7—C4—C3110.1 (10)O3'—C6'—O2'123.5 (14)
O7—C4—C5105.0 (9)O3'—C6'—C7'126.8 (14)
C3—C4—C5110.0 (9)O2'—C6'—C7'109.7 (12)
O5—C5—C12103.9 (10)O6'—C8'—O4'122.2 (11)
O5—C5—C4108.6 (8)O6'—C8'—C9'126.6 (13)
C12—C5—C4115.4 (9)O4'—C8'—C9'111.3 (11)
O3—C6—O2122.9 (13)O8'—C10'—O7'119.2 (12)
O3—C6—C7124.4 (13)O8'—C10'—C11'129.6 (13)
O2—C6—C7112.4 (12)O7'—C10'—C11'111.1 (10)
O6—C8—O4124.0 (12)O9'—C12'—C5'104.3 (8)
O6—C8—C9127.2 (13)O10'—C13'—O9'125.3 (11)
O4—C8—C9108.8 (10)O10'—C13'—C14'124.8 (12)
O8—C10—O7123.4 (11)O9'—C13'—C14'109.9 (11)
O8—C10—C11122.7 (11)C15'—C14'—C13'112.8 (12)
O7—C10—C11113.4 (10)C15'—C14'—C16'110.5 (11)
O9—C12—C5107.5 (8)C13'—C14'—C16'108.3 (11)
O10—C13—O9122.3 (11)
C5—O5—C1—O154.7 (11)C5'—O5'—C1'—O154.3 (11)
C5—O5—C1—C260.8 (11)C5'—O5'—C1'—C2'62.2 (12)
C1'—O1—C1—O582.2 (12)C1—O1—C1'—O5'69.9 (12)
C1'—O1—C1—C2158.7 (9)C1—O1—C1'—C2'170.1 (9)
C6—O2—C2—C3144.2 (10)C6'—O2'—C2'—C1'87.0 (12)
C6—O2—C2—C194.5 (12)C6'—O2'—C2'—C3'156.0 (9)
O5—C1—C2—O2173.3 (9)O5'—C1'—C2'—O2'177.6 (9)
O1—C1—C2—O253.3 (12)O1—C1'—C2'—O2'56.1 (12)
O5—C1—C2—C356.3 (13)O5'—C1'—C2'—C3'63.1 (12)
O1—C1—C2—C363.8 (12)O1—C1'—C2'—C3'58.4 (11)
C8—O4—C3—C2134.1 (11)C8'—O4'—C3'—C4'104.0 (12)
C8—O4—C3—C4105.9 (12)C8'—O4'—C3'—C2'138.6 (10)
O2—C2—C3—O466.6 (10)O2'—C2'—C3'—O4'67.8 (10)
C1—C2—C3—O4172.3 (9)C1'—C2'—C3'—O4'173.9 (8)
O2—C2—C3—C4174.3 (8)O2'—C2'—C3'—C4'174.7 (7)
C1—C2—C3—C453.2 (12)C1'—C2'—C3'—C4'56.4 (11)
C10—O7—C4—C392.0 (12)C10'—O7'—C4'—C3'101.3 (11)
C10—O7—C4—C5149.7 (10)C10'—O7'—C4'—C5'137.8 (10)
O4—C3—C4—O772.4 (10)O4'—C3'—C4'—O7'78.7 (10)
C2—C3—C4—O7168.7 (8)C2'—C3'—C4'—O7'164.9 (7)
O4—C3—C4—C5172.5 (8)O4'—C3'—C4'—C5'166.7 (9)
C2—C3—C4—C553.5 (12)C2'—C3'—C4'—C5'50.4 (12)
C1—O5—C5—C12175.5 (7)C1'—O5'—C5'—C12'179.1 (8)
C1—O5—C5—C461.1 (11)C1'—O5'—C5'—C4'53.8 (11)
O7—C4—C5—O5174.5 (8)O7'—C4'—C5'—O5'166.7 (8)
C3—C4—C5—O556.1 (12)C3'—C4'—C5'—O5'48.0 (13)
O7—C4—C5—C1269.4 (12)O7'—C4'—C5'—C12'71.2 (12)
C3—C4—C5—C12172.2 (10)C3'—C4'—C5'—C12'170.1 (10)
C2—O2—C6—O34.1 (19)C2'—O2'—C6'—O3'1.0 (18)
C2—O2—C6—C7177.8 (9)C2'—O2'—C6'—C7'179.9 (9)
C3—O4—C8—O62 (2)C3'—O4'—C8'—O6'13.8 (18)
C3—O4—C8—C9178.1 (10)C3'—O4'—C8'—C9'166.4 (9)
C4—O7—C10—O82.0 (19)C4'—O7'—C10'—O8'3.8 (18)
C4—O7—C10—C11170.8 (11)C4'—O7'—C10'—C11'179.8 (9)
C13—O9—C12—C5172.8 (10)C13'—O9'—C12'—C5'152.9 (10)
O5—C5—C12—O974.1 (10)O5'—C5'—C12'—O9'74.4 (10)
C4—C5—C12—O9167.2 (9)C4'—C5'—C12'—O9'161.1 (9)
C12—O9—C13—O109.9 (19)C12'—O9'—C13'—O10'3.0 (19)
C12—O9—C13—C14175.3 (10)C12'—O9'—C13'—C14'178.5 (10)
O10—C13—C14—C1626 (2)O10'—C13'—C14'—C15'115.0 (15)
O9—C13—C14—C16148.2 (11)O9'—C13'—C14'—C15'63.6 (15)
O10—C13—C14—C1594.7 (17)O10'—C13'—C14'—C16'122.4 (15)
O9—C13—C14—C1590.9 (13)O9'—C13'—C14'—C16'59.1 (15)

Experimental details

Crystal data
Chemical formulaC32H46O19·0.7H2O
Mr747.30
Crystal system, space groupOrthorhombic, P212121
Temperature (K)150
a, b, c (Å)8.857 (3), 17.813 (11), 24.085 (3)
V3)3800 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.21 × 0.10 × 0.10
Data collection
DiffractometerDelft Instruments FAST
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
17076, 3541, 565
Rint0.311
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.100, 0.39
No. of reflections3541
No. of parameters460
No. of restraints117
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.17

Computer programs: MADNES (Plugrath & Messerschmidt, 1989), MADNES, ABSMAD (Karaulov, 1992), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

 

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