Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800020705/cf6028sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800020705/cf6028Isup2.hkl |
CCDC reference: 155897
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.
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.
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.
Fig. 1. The atomic arrangement in the title molecule. Displacement ellipsoids are shown at the 50% probability level. |
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) Å3 | Lozenge, colourless |
Z = 4 | 0.21 × 0.10 × 0.10 mm |
F(000) = 1588 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 0.39 | w = 1/[σ2(Fo2)] |
3541 reflections | (Δ/σ)max < 0.001 |
460 parameters | Δρmax = 0.19 e Å−3 |
117 restraints | Δρmin = −0.17 e Å−3 |
C32H46O19·0.7H2O | V = 3800 (3) Å3 |
Mr = 747.30 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.857 (3) Å | µ = 0.11 mm−1 |
b = 17.813 (11) Å | T = 150 K |
c = 24.085 (3) Å | 0.21 × 0.10 × 0.10 mm |
Delft Instruments FAST diffractometer | 565 reflections with I > 2σ(I) |
17076 measured reflections | Rint = 0.311 |
3541 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 117 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 0.39 | Δρmax = 0.19 e Å−3 |
3541 reflections | Δρmin = −0.17 e Å−3 |
460 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
Experimental details
Crystal data | |
Chemical formula | C32H46O19·0.7H2O |
Mr | 747.30 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 150 |
a, b, c (Å) | 8.857 (3), 17.813 (11), 24.085 (3) |
V (Å3) | 3800 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.21 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Delft Instruments FAST diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17076, 3541, 565 |
Rint | 0.311 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.100, 0.39 |
No. of reflections | 3541 |
No. of parameters | 460 |
No. of restraints | 117 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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.
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).