Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006857/bt6040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006857/bt6040Isup2.hkl |
CCDC reference: 165669
The title compound was prepared by reacting anhydrous α,α-trehalose with acetic anhydride. Purification was achieved through a combination of column chromatography and recrystallization from methanol. Crystals for X-ray work were obtained by slow evaporation from ethyl acetate.
The H atoms were initially placed in calculated positions and thereafter allowed to ride on their attached atoms. Each H atom was given an equivalent isotropic displacement parameter 1.2 greater than their attached atom. The H atoms of the methyl groups were allowed to rotate about the local threefold axes to maximize the sum of the electron density at the calculated H-atom positions.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al.,1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).
Fig. 1. The atomic arrangement in the title molecule. Displacement ellipsoids are shown at the 50% probability level. |
C28H38O19·C4H8O2 | Dx = 1.323 Mg m−3 |
Mr = 766.69 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 4833 reflections |
a = 14.1406 (1) Å | θ = 2.0–27.3° |
b = 15.2215 (1) Å | µ = 0.11 mm−1 |
c = 17.8879 (2) Å | T = 293 K |
V = 3850.21 (6) Å3 | Prism, colourless |
Z = 4 | 0.4 × 0.3 × 0.2 mm |
F(000) = 1624 |
Enraf-Nonius KappaCCD area-detector diffractometer | 4833 independent reflections |
Radiation source: Enraf-Nonius FR591 rotating anode | 3409 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.0° |
ϕ and ω scans to fill Ewald sphere | h = −17→18 |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) | k = −18→18 |
Tmin = 0.957, Tmax = 0.978 | l = −23→23 |
41400 measured reflections |
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) = 0.096 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0569P)2] where P = (Fo2 + 2Fc2)/3 |
4833 reflections | (Δ/σ)max = 0.002 |
488 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C28H38O19·C4H8O2 | V = 3850.21 (6) Å3 |
Mr = 766.69 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 14.1406 (1) Å | µ = 0.11 mm−1 |
b = 15.2215 (1) Å | T = 293 K |
c = 17.8879 (2) Å | 0.4 × 0.3 × 0.2 mm |
Enraf-Nonius KappaCCD area-detector diffractometer | 4833 independent reflections |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) | 3409 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.978 | Rint = 0.084 |
41400 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.54 e Å−3 |
4833 reflections | Δρmin = −0.34 e Å−3 |
488 parameters |
Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
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 | ||
O1 | 0.24761 (12) | 0.50657 (11) | 0.69258 (8) | 0.0198 (4) | |
O2 | 0.35494 (11) | 0.49212 (12) | 0.82096 (9) | 0.0240 (4) | |
O3 | 0.37678 (14) | 0.62401 (14) | 0.87406 (12) | 0.0396 (5) | |
O4 | 0.23379 (13) | 0.37729 (11) | 0.89904 (9) | 0.0233 (4) | |
O5 | 0.12059 (11) | 0.56622 (12) | 0.75952 (9) | 0.0219 (4) | |
O6 | 0.29369 (16) | 0.25888 (13) | 0.84058 (11) | 0.0447 (6) | |
O7 | 0.05778 (13) | 0.34412 (11) | 0.81954 (9) | 0.0248 (4) | |
O8 | −0.00552 (17) | 0.34988 (14) | 0.93443 (11) | 0.0511 (6) | |
O9 | −0.07106 (13) | 0.54943 (13) | 0.70486 (11) | 0.0350 (5) | |
O10 | −0.1617 (2) | 0.43297 (16) | 0.67996 (14) | 0.0618 (7) | |
C1 | 0.21990 (16) | 0.55554 (16) | 0.75623 (13) | 0.0188 (5) | |
H1 | 0.2501 | 0.6134 | 0.7547 | 0.023* | |
C2 | 0.25432 (17) | 0.50563 (17) | 0.82486 (13) | 0.0201 (5) | |
H2 | 0.2391 | 0.5393 | 0.8700 | 0.024* | |
C3 | 0.20747 (17) | 0.41666 (16) | 0.82907 (13) | 0.0190 (5) | |
H3 | 0.2274 | 0.3796 | 0.7871 | 0.023* | |
C4 | 0.10119 (17) | 0.42917 (17) | 0.82853 (13) | 0.0208 (5) | |
H4 | 0.0804 | 0.4561 | 0.8755 | 0.025* | |
C5 | 0.06921 (17) | 0.48476 (16) | 0.76238 (14) | 0.0220 (5) | |
H5 | 0.0784 | 0.4521 | 0.7157 | 0.026* | |
C6 | −0.03384 (18) | 0.5084 (2) | 0.77136 (16) | 0.0324 (7) | |
H6A | −0.0699 | 0.4556 | 0.7821 | 0.039* | |
H6B | −0.0409 | 0.5482 | 0.8134 | 0.039* | |
C7 | 0.40958 (19) | 0.55695 (19) | 0.84991 (14) | 0.0264 (6) | |
C8 | 0.5118 (2) | 0.5332 (2) | 0.84639 (17) | 0.0361 (7) | |
H8A | 0.5475 | 0.5729 | 0.8771 | 0.043* | |
H8B | 0.5334 | 0.5373 | 0.7956 | 0.043* | |
H8C | 0.5202 | 0.4742 | 0.8642 | 0.043* | |
C9 | 0.27802 (19) | 0.29815 (18) | 0.89714 (15) | 0.0280 (6) | |
C10 | 0.3050 (2) | 0.27072 (19) | 0.97357 (15) | 0.0390 (7) | |
H10A | 0.3269 | 0.2111 | 0.9726 | 0.047* | |
H10B | 0.2511 | 0.2751 | 1.0060 | 0.047* | |
H10C | 0.3545 | 0.3082 | 0.9918 | 0.047* | |
C11 | 0.00421 (19) | 0.31286 (18) | 0.87611 (15) | 0.0282 (6) | |
C12 | −0.0418 (2) | 0.2294 (2) | 0.85412 (19) | 0.0472 (9) | |
H12A | −0.1057 | 0.2409 | 0.8389 | 0.057* | |
H12B | −0.0419 | 0.1898 | 0.8959 | 0.057* | |
H12C | −0.0076 | 0.2035 | 0.8133 | 0.057* | |
C13 | −0.1377 (2) | 0.5059 (2) | 0.66567 (17) | 0.0371 (7) | |
C14 | −0.1751 (3) | 0.5612 (2) | 0.60460 (19) | 0.0553 (9) | |
H14A | −0.2152 | 0.6061 | 0.6251 | 0.066* | |
H14B | −0.2110 | 0.5255 | 0.5707 | 0.066* | |
H14C | −0.1235 | 0.5881 | 0.5783 | 0.066* | |
O2' | 0.17063 (12) | 0.43271 (11) | 0.56594 (9) | 0.0247 (4) | |
O3' | 0.07217 (15) | 0.53484 (14) | 0.51939 (13) | 0.0420 (5) | |
O4' | 0.33362 (13) | 0.39523 (11) | 0.48537 (9) | 0.0232 (4) | |
O5' | 0.33080 (12) | 0.61010 (11) | 0.62208 (9) | 0.0232 (4) | |
O6' | 0.38886 (16) | 0.26963 (13) | 0.53495 (11) | 0.0417 (5) | |
O7' | 0.50650 (12) | 0.44301 (12) | 0.57832 (9) | 0.0253 (4) | |
O8' | 0.54067 (14) | 0.42584 (15) | 0.45635 (10) | 0.0412 (5) | |
O9' | 0.4719 (2) | 0.80295 (16) | 0.63503 (14) | 0.0659 (8) | |
O10' | 0.49899 (14) | 0.67524 (12) | 0.69349 (9) | 0.0324 (5) | |
C1' | 0.24934 (18) | 0.55685 (16) | 0.62600 (13) | 0.0215 (5) | |
H1' | 0.1929 | 0.5941 | 0.6240 | 0.026* | |
C2' | 0.24842 (17) | 0.49390 (17) | 0.56036 (13) | 0.0204 (5) | |
H2' | 0.2422 | 0.5276 | 0.5139 | 0.025* | |
C3' | 0.33764 (17) | 0.43937 (16) | 0.55684 (13) | 0.0205 (5) | |
H3' | 0.3381 | 0.3961 | 0.5974 | 0.025* | |
C4' | 0.42535 (17) | 0.49699 (16) | 0.56123 (13) | 0.0216 (5) | |
H4' | 0.4350 | 0.5285 | 0.5141 | 0.026* | |
C5' | 0.41790 (17) | 0.56145 (17) | 0.62628 (14) | 0.0222 (5) | |
H5' | 0.4206 | 0.5293 | 0.6737 | 0.027* | |
C6' | 0.4969 (2) | 0.62841 (19) | 0.62355 (15) | 0.0308 (6) | |
H6'A | 0.5569 | 0.5991 | 0.6153 | 0.037* | |
H6'B | 0.4863 | 0.6692 | 0.5827 | 0.037* | |
C7' | 0.08524 (19) | 0.4614 (2) | 0.54100 (14) | 0.0283 (6) | |
C8' | 0.0144 (2) | 0.3895 (2) | 0.54421 (16) | 0.0398 (7) | |
H8'A | −0.0462 | 0.4115 | 0.5288 | 0.048* | |
H8'B | 0.0101 | 0.3677 | 0.5945 | 0.048* | |
H8'C | 0.0334 | 0.3427 | 0.5115 | 0.048* | |
C9' | 0.35853 (18) | 0.30908 (17) | 0.48195 (15) | 0.0255 (6) | |
C10' | 0.3451 (2) | 0.27493 (19) | 0.40502 (15) | 0.0334 (7) | |
H10D | 0.3494 | 0.2120 | 0.4055 | 0.040* | |
H10E | 0.3932 | 0.2985 | 0.3729 | 0.040* | |
H10F | 0.2840 | 0.2922 | 0.3869 | 0.040* | |
C11' | 0.55735 (19) | 0.40935 (18) | 0.52039 (16) | 0.0294 (6) | |
C12' | 0.6326 (2) | 0.3503 (2) | 0.54965 (16) | 0.0374 (7) | |
H12D | 0.6811 | 0.3435 | 0.5126 | 0.045* | |
H12E | 0.6058 | 0.2939 | 0.5612 | 0.045* | |
H12F | 0.6594 | 0.3754 | 0.5941 | 0.045* | |
C13' | 0.4874 (2) | 0.7633 (2) | 0.69125 (18) | 0.0431 (8) | |
C14' | 0.4987 (3) | 0.8022 (2) | 0.76725 (19) | 0.0660 (11) | |
H14D | 0.4592 | 0.8532 | 0.7716 | 0.079* | |
H14E | 0.5635 | 0.8186 | 0.7748 | 0.079* | |
H14F | 0.4806 | 0.7597 | 0.8043 | 0.079* | |
O11 | 0.74712 (16) | 0.56486 (15) | 0.82116 (12) | 0.0490 (6) | |
O12 | 0.71925 (17) | 0.55070 (17) | 0.94391 (12) | 0.0548 (6) | |
C15 | 0.8210 (3) | 0.7094 (2) | 0.8284 (2) | 0.0550 (9) | |
H15A | 0.8571 | 0.6980 | 0.7840 | 0.066* | |
H15B | 0.8570 | 0.6919 | 0.8715 | 0.066* | |
H15C | 0.8070 | 0.7710 | 0.8315 | 0.066* | |
C16 | 0.7312 (2) | 0.6585 (2) | 0.82579 (19) | 0.0456 (8) | |
H16A | 0.6945 | 0.6712 | 0.8703 | 0.055* | |
H16B | 0.6947 | 0.6772 | 0.7828 | 0.055* | |
C17 | 0.7390 (2) | 0.5199 (2) | 0.8839 (2) | 0.0459 (8) | |
C18 | 0.7531 (3) | 0.4221 (3) | 0.8711 (2) | 0.0674 (11) | |
H18A | 0.6982 | 0.3907 | 0.8880 | 0.081* | |
H18B | 0.8075 | 0.4024 | 0.8984 | 0.081* | |
H18C | 0.7623 | 0.4112 | 0.8187 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0229 (9) | 0.0183 (8) | 0.0182 (8) | −0.0004 (8) | 0.0047 (7) | 0.0010 (7) |
O2 | 0.0195 (9) | 0.0256 (9) | 0.0268 (9) | −0.0002 (8) | −0.0012 (7) | −0.0016 (8) |
O3 | 0.0302 (11) | 0.0328 (12) | 0.0557 (13) | −0.0046 (10) | −0.0040 (10) | −0.0127 (10) |
O4 | 0.0304 (10) | 0.0220 (9) | 0.0176 (9) | 0.0040 (8) | −0.0001 (7) | 0.0009 (7) |
O5 | 0.0191 (9) | 0.0234 (9) | 0.0231 (9) | −0.0002 (7) | 0.0021 (7) | 0.0014 (7) |
O6 | 0.0684 (16) | 0.0346 (12) | 0.0312 (11) | 0.0202 (11) | −0.0044 (10) | −0.0064 (9) |
O7 | 0.0273 (10) | 0.0218 (9) | 0.0253 (9) | −0.0078 (8) | 0.0038 (8) | −0.0042 (7) |
O8 | 0.0765 (17) | 0.0455 (13) | 0.0314 (11) | −0.0313 (13) | 0.0196 (12) | −0.0086 (10) |
O9 | 0.0269 (11) | 0.0413 (12) | 0.0368 (11) | −0.0018 (10) | −0.0098 (8) | 0.0084 (9) |
O10 | 0.0861 (19) | 0.0407 (14) | 0.0587 (15) | −0.0096 (15) | −0.0148 (14) | −0.0125 (12) |
C1 | 0.0177 (13) | 0.0180 (13) | 0.0207 (12) | 0.0004 (10) | 0.0021 (9) | −0.0033 (10) |
C2 | 0.0169 (12) | 0.0237 (13) | 0.0196 (12) | 0.0001 (11) | 0.0027 (10) | 0.0001 (10) |
C3 | 0.0222 (13) | 0.0212 (13) | 0.0136 (12) | 0.0007 (10) | 0.0000 (9) | 0.0018 (10) |
C4 | 0.0226 (13) | 0.0209 (13) | 0.0190 (13) | −0.0036 (11) | 0.0019 (10) | −0.0017 (11) |
C5 | 0.0192 (13) | 0.0256 (14) | 0.0212 (13) | −0.0014 (11) | 0.0008 (10) | 0.0009 (11) |
C6 | 0.0207 (14) | 0.0432 (17) | 0.0332 (15) | −0.0006 (13) | −0.0005 (11) | 0.0113 (13) |
C7 | 0.0229 (14) | 0.0286 (16) | 0.0278 (14) | −0.0065 (13) | −0.0015 (11) | 0.0028 (12) |
C8 | 0.0217 (15) | 0.0430 (18) | 0.0437 (17) | −0.0053 (13) | −0.0048 (12) | 0.0053 (14) |
C9 | 0.0291 (15) | 0.0237 (14) | 0.0313 (15) | 0.0002 (12) | −0.0019 (11) | 0.0022 (12) |
C10 | 0.056 (2) | 0.0273 (16) | 0.0335 (16) | 0.0078 (14) | −0.0074 (14) | 0.0041 (13) |
C11 | 0.0314 (15) | 0.0257 (15) | 0.0276 (14) | −0.0065 (12) | 0.0042 (12) | 0.0006 (12) |
C12 | 0.051 (2) | 0.0342 (18) | 0.057 (2) | −0.0168 (16) | 0.0208 (16) | −0.0109 (16) |
C13 | 0.0327 (16) | 0.0384 (19) | 0.0403 (17) | 0.0089 (15) | −0.0049 (12) | −0.0122 (14) |
C14 | 0.058 (2) | 0.055 (2) | 0.052 (2) | 0.016 (2) | −0.0237 (17) | −0.0106 (17) |
O2' | 0.0228 (9) | 0.0245 (9) | 0.0268 (9) | −0.0045 (8) | 0.0000 (7) | −0.0001 (8) |
O3' | 0.0297 (12) | 0.0381 (13) | 0.0581 (14) | 0.0002 (10) | −0.0094 (10) | 0.0038 (11) |
O4' | 0.0306 (10) | 0.0178 (9) | 0.0212 (9) | 0.0034 (8) | −0.0006 (8) | −0.0019 (7) |
O5' | 0.0254 (9) | 0.0201 (9) | 0.0242 (9) | −0.0027 (8) | 0.0032 (8) | 0.0012 (7) |
O6' | 0.0623 (15) | 0.0266 (11) | 0.0363 (12) | 0.0119 (10) | −0.0011 (10) | 0.0025 (9) |
O7' | 0.0227 (9) | 0.0291 (10) | 0.0241 (9) | 0.0024 (8) | 0.0009 (7) | −0.0005 (8) |
O8' | 0.0406 (12) | 0.0567 (14) | 0.0263 (11) | 0.0167 (11) | 0.0079 (9) | 0.0025 (10) |
O9' | 0.108 (2) | 0.0369 (14) | 0.0532 (15) | 0.0125 (14) | −0.0084 (15) | 0.0014 (12) |
O10' | 0.0407 (12) | 0.0288 (11) | 0.0276 (10) | −0.0099 (9) | 0.0002 (8) | −0.0051 (8) |
C1' | 0.0208 (13) | 0.0201 (13) | 0.0237 (12) | 0.0018 (11) | 0.0009 (11) | 0.0029 (10) |
C2' | 0.0201 (13) | 0.0215 (13) | 0.0197 (12) | −0.0007 (11) | 0.0020 (10) | 0.0036 (10) |
C3' | 0.0262 (13) | 0.0206 (13) | 0.0148 (11) | 0.0006 (12) | −0.0009 (10) | 0.0004 (10) |
C4' | 0.0232 (13) | 0.0215 (13) | 0.0201 (13) | 0.0026 (12) | 0.0022 (10) | 0.0017 (11) |
C5' | 0.0210 (13) | 0.0230 (13) | 0.0225 (13) | −0.0013 (11) | 0.0026 (10) | 0.0028 (11) |
C6' | 0.0323 (16) | 0.0331 (16) | 0.0268 (14) | −0.0083 (13) | 0.0043 (12) | −0.0074 (12) |
C7' | 0.0226 (15) | 0.0369 (18) | 0.0254 (15) | −0.0014 (13) | 0.0008 (11) | −0.0056 (12) |
C8' | 0.0323 (17) | 0.0478 (19) | 0.0393 (17) | −0.0096 (15) | 0.0021 (13) | −0.0054 (14) |
C9' | 0.0262 (15) | 0.0204 (14) | 0.0299 (14) | 0.0019 (11) | 0.0039 (11) | −0.0003 (12) |
C10' | 0.0386 (17) | 0.0276 (15) | 0.0339 (15) | 0.0025 (14) | 0.0014 (13) | −0.0080 (12) |
C11' | 0.0262 (15) | 0.0308 (15) | 0.0313 (16) | 0.0000 (12) | 0.0082 (12) | −0.0001 (12) |
C12' | 0.0315 (16) | 0.0411 (18) | 0.0397 (17) | 0.0104 (14) | 0.0058 (13) | 0.0020 (14) |
C13' | 0.052 (2) | 0.0328 (18) | 0.0445 (19) | −0.0065 (16) | 0.0037 (15) | −0.0057 (15) |
C14' | 0.102 (3) | 0.046 (2) | 0.051 (2) | −0.012 (2) | 0.008 (2) | −0.0194 (17) |
O11 | 0.0480 (13) | 0.0491 (14) | 0.0499 (13) | 0.0045 (12) | 0.0118 (11) | 0.0089 (11) |
O12 | 0.0546 (15) | 0.0721 (18) | 0.0376 (13) | −0.0106 (13) | −0.0039 (11) | 0.0091 (12) |
C15 | 0.062 (2) | 0.047 (2) | 0.056 (2) | 0.0005 (19) | 0.0007 (18) | 0.0093 (17) |
C16 | 0.050 (2) | 0.0387 (18) | 0.0486 (19) | 0.0053 (16) | 0.0095 (16) | 0.0055 (15) |
C17 | 0.0206 (16) | 0.062 (2) | 0.055 (2) | −0.0041 (15) | −0.0004 (14) | 0.0170 (18) |
C18 | 0.052 (2) | 0.056 (2) | 0.094 (3) | 0.007 (2) | 0.021 (2) | 0.028 (2) |
O1—C1' | 1.416 (3) | O3'—C7' | 1.197 (3) |
O1—C1 | 1.416 (3) | O4'—C9' | 1.359 (3) |
O2—C7 | 1.356 (3) | O4'—C3' | 1.445 (3) |
O2—C2 | 1.439 (3) | O5'—C1' | 1.410 (3) |
O3—C7 | 1.201 (3) | O5'—C5' | 1.439 (3) |
O4—C9 | 1.358 (3) | O6'—C9' | 1.202 (3) |
O4—C3 | 1.437 (3) | O7'—C11' | 1.361 (3) |
O5—C1 | 1.415 (3) | O7'—C4' | 1.444 (3) |
O5—C5 | 1.438 (3) | O8'—C11' | 1.196 (3) |
O6—C9 | 1.196 (3) | O9'—C13' | 1.193 (4) |
O7—C11 | 1.351 (3) | O10'—C13' | 1.351 (4) |
O7—C4 | 1.442 (3) | O10'—C6' | 1.440 (3) |
O8—C11 | 1.194 (3) | C1'—C2' | 1.516 (3) |
O9—C13 | 1.348 (4) | C2'—C3' | 1.512 (4) |
O9—C6 | 1.443 (3) | C3'—C4' | 1.521 (3) |
O10—C13 | 1.189 (4) | C4'—C5' | 1.526 (3) |
C1—C2 | 1.523 (3) | C5'—C6' | 1.513 (4) |
C2—C3 | 1.510 (3) | C7'—C8' | 1.486 (4) |
C3—C4 | 1.515 (3) | C9'—C10' | 1.483 (4) |
C4—C5 | 1.523 (3) | C11'—C12' | 1.488 (4) |
C5—C6 | 1.510 (4) | C13'—C14' | 1.491 (4) |
C7—C8 | 1.491 (4) | O11—C17 | 1.319 (4) |
C9—C10 | 1.479 (4) | O11—C16 | 1.445 (4) |
C11—C12 | 1.480 (4) | O12—C17 | 1.204 (4) |
C13—C14 | 1.477 (4) | C15—C16 | 1.488 (5) |
O2'—C7' | 1.359 (3) | C17—C18 | 1.520 (5) |
O2'—C2' | 1.445 (3) | ||
C1'—O1—C1 | 113.36 (17) | C1'—O5'—C5' | 113.63 (17) |
C7—O2—C2 | 116.1 (2) | C11'—O7'—C4' | 118.20 (19) |
C9—O4—C3 | 117.88 (19) | C13'—O10'—C6' | 117.6 (2) |
C1—O5—C5 | 113.81 (19) | O5'—C1'—O1 | 111.50 (19) |
C11—O7—C4 | 118.13 (19) | O5'—C1'—C2' | 109.38 (19) |
C13—O9—C6 | 118.1 (2) | O1—C1'—C2' | 108.04 (19) |
O5—C1—O1 | 111.63 (18) | O2'—C2'—C3' | 106.5 (2) |
O5—C1—C2 | 109.93 (18) | O2'—C2'—C1' | 111.13 (19) |
O1—C1—C2 | 107.28 (19) | C3'—C2'—C1' | 111.9 (2) |
O2—C2—C3 | 107.9 (2) | O4'—C3'—C2' | 105.02 (18) |
O2—C2—C1 | 110.37 (18) | O4'—C3'—C4' | 110.23 (19) |
C3—C2—C1 | 110.32 (19) | C2'—C3'—C4' | 111.2 (2) |
O4—C3—C2 | 107.69 (18) | O7'—C4'—C3' | 109.31 (19) |
O4—C3—C4 | 108.36 (18) | O7'—C4'—C5' | 105.03 (18) |
C2—C3—C4 | 108.8 (2) | C3'—C4'—C5' | 110.72 (19) |
O7—C4—C3 | 108.1 (2) | O5'—C5'—C6' | 106.5 (2) |
O7—C4—C5 | 106.60 (19) | O5'—C5'—C4' | 110.50 (19) |
C3—C4—C5 | 111.7 (2) | C6'—C5'—C4' | 111.0 (2) |
O5—C5—C6 | 106.6 (2) | O10'—C6'—C5' | 108.7 (2) |
O5—C5—C4 | 110.89 (19) | O3'—C7'—O2' | 122.9 (3) |
C6—C5—C4 | 109.7 (2) | O3'—C7'—C8' | 126.6 (3) |
O9—C6—C5 | 111.6 (2) | O2'—C7'—C8' | 110.5 (3) |
O3—C7—O2 | 122.4 (2) | O6'—C9'—O4' | 122.6 (2) |
O3—C7—C8 | 126.5 (3) | O6'—C9'—C10' | 127.1 (2) |
O2—C7—C8 | 111.1 (2) | O4'—C9'—C10' | 110.3 (2) |
O6—C9—O4 | 123.4 (2) | O8'—C11'—O7' | 123.1 (2) |
O6—C9—C10 | 126.4 (2) | O8'—C11'—C12' | 127.2 (3) |
O4—C9—C10 | 110.2 (2) | O7'—C11'—C12' | 109.7 (2) |
O8—C11—O7 | 123.6 (2) | O9'—C13'—O10' | 123.3 (3) |
O8—C11—C12 | 125.9 (3) | O9'—C13'—C14' | 126.0 (3) |
O7—C11—C12 | 110.5 (2) | O10'—C13'—C14' | 110.7 (3) |
O10—C13—O9 | 123.1 (3) | C17—O11—C16 | 116.7 (3) |
O10—C13—C14 | 126.1 (3) | O11—C16—C15 | 112.5 (3) |
O9—C13—C14 | 110.8 (3) | O12—C17—O11 | 125.2 (3) |
C7'—O2'—C2' | 116.5 (2) | O12—C17—C18 | 123.1 (3) |
C9'—O4'—C3' | 118.56 (19) | O11—C17—C18 | 111.6 (3) |
C5—O5—C1—O1 | 59.3 (2) | C1—O1—C1'—O5' | 77.7 (2) |
C5—O5—C1—C2 | −59.6 (2) | C1—O1—C1'—C2' | −162.07 (19) |
C1'—O1—C1—O5 | 79.5 (2) | C7'—O2'—C2'—C3' | −155.0 (2) |
C1'—O1—C1—C2 | −160.06 (19) | C7'—O2'—C2'—C1' | 83.0 (2) |
C7—O2—C2—C3 | −151.17 (19) | O5'—C1'—C2'—O2' | 174.74 (18) |
C7—O2—C2—C1 | 88.2 (2) | O1—C1'—C2'—O2' | 53.2 (3) |
O5—C1—C2—O2 | 178.29 (19) | O5'—C1'—C2'—C3' | 55.8 (3) |
O1—C1—C2—O2 | 56.7 (2) | O1—C1'—C2'—C3' | −65.7 (2) |
O5—C1—C2—C3 | 59.1 (2) | C9'—O4'—C3'—C2' | −137.4 (2) |
O1—C1—C2—C3 | −62.5 (2) | C9'—O4'—C3'—C4' | 102.8 (2) |
C9—O4—C3—C2 | −122.3 (2) | O2'—C2'—C3'—O4' | 68.3 (2) |
C9—O4—C3—C4 | 120.1 (2) | C1'—C2'—C3'—O4' | −170.08 (18) |
O2—C2—C3—O4 | 66.1 (2) | O2'—C2'—C3'—C4' | −172.47 (19) |
C1—C2—C3—O4 | −173.23 (18) | C1'—C2'—C3'—C4' | −50.9 (3) |
O2—C2—C3—C4 | −176.64 (18) | C11'—O7'—C4'—C3' | 91.2 (2) |
C1—C2—C3—C4 | −56.0 (2) | C11'—O7'—C4'—C5' | −149.9 (2) |
C11—O7—C4—C3 | 115.5 (2) | O4'—C3'—C4'—O7' | −79.6 (2) |
C11—O7—C4—C5 | −124.3 (2) | C2'—C3'—C4'—O7' | 164.37 (18) |
O4—C3—C4—O7 | −72.9 (2) | O4'—C3'—C4'—C5' | 165.19 (19) |
C2—C3—C4—O7 | 170.24 (17) | C2'—C3'—C4'—C5' | 49.1 (3) |
O4—C3—C4—C5 | 170.13 (18) | C1'—O5'—C5'—C6' | −178.4 (2) |
C2—C3—C4—C5 | 53.3 (3) | C1'—O5'—C5'—C4' | 61.0 (2) |
C1—O5—C5—C6 | 175.94 (19) | O7'—C4'—C5'—O5' | −170.84 (18) |
C1—O5—C5—C4 | 56.6 (2) | C3'—C4'—C5'—O5' | −52.9 (2) |
O7—C4—C5—O5 | −170.68 (17) | O7'—C4'—C5'—C6' | 71.3 (3) |
C3—C4—C5—O5 | −52.9 (3) | C3'—C4'—C5'—C6' | −170.8 (2) |
O7—C4—C5—C6 | 71.8 (3) | C13'—O10'—C6'—C5' | −120.9 (3) |
C3—C4—C5—C6 | −170.3 (2) | O5'—C5'—C6'—O10' | 71.9 (3) |
C13—O9—C6—C5 | 113.7 (3) | C4'—C5'—C6'—O10' | −167.8 (2) |
O5—C5—C6—O9 | 68.7 (3) | C2'—O2'—C7'—O3' | −4.3 (4) |
C4—C5—C6—O9 | −171.2 (2) | C2'—O2'—C7'—C8' | 175.2 (2) |
C2—O2—C7—O3 | −3.7 (3) | C3'—O4'—C9'—O6' | −4.4 (4) |
C2—O2—C7—C8 | 176.9 (2) | C3'—O4'—C9'—C10' | 177.2 (2) |
C3—O4—C9—O6 | −2.1 (4) | C4'—O7'—C11'—O8' | 3.7 (4) |
C3—O4—C9—C10 | 176.4 (2) | C4'—O7'—C11'—C12' | −175.5 (2) |
C4—O7—C11—O8 | −3.7 (4) | C6'—O10'—C13'—O9' | 3.0 (5) |
C4—O7—C11—C12 | 174.5 (2) | C6'—O10'—C13'—C14' | −175.7 (3) |
C6—O9—C13—O10 | −6.0 (4) | C17—O11—C16—C15 | 100.1 (3) |
C6—O9—C13—C14 | 173.7 (3) | C16—O11—C17—O12 | 0.3 (5) |
C5'—O5'—C1'—O1 | 57.8 (2) | C16—O11—C17—C18 | 177.5 (3) |
C5'—O5'—C1'—C2' | −61.6 (2) |
Experimental details
Crystal data | |
Chemical formula | C28H38O19·C4H8O2 |
Mr | 766.69 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 14.1406 (1), 15.2215 (1), 17.8879 (2) |
V (Å3) | 3850.21 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.4 × 0.3 × 0.2 |
Data collection | |
Diffractometer | Enraf-Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) |
Tmin, Tmax | 0.957, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 41400, 4833, 3409 |
Rint | 0.084 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.096, 1.00 |
No. of reflections | 4833 |
No. of parameters | 488 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.54, −0.34 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SIR97 (Altomare et al.,1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).
O1—C1' | 1.416 (3) | O5—C5 | 1.438 (3) |
O1—C1 | 1.416 (3) | O5'—C1' | 1.410 (3) |
O5—C1 | 1.415 (3) | O5'—C5' | 1.439 (3) |
C1'—O1—C1 | 113.36 (17) | O4'—C3'—C2' | 105.02 (18) |
C1—O5—C5 | 113.81 (19) | O8'—C11'—C12' | 127.2 (3) |
C1'—O5'—C5' | 113.63 (17) |
Trehalose is implicated in the preservation of life without water (Branca et al., 1999) and it is used in certain drug formulations (Hatley & Blair, 1999). The role of hydrogen bonding in trehalose and its derivatives is of continuing interest (Clow et al., 2001). Polymorphic forms of α,α-trehalose octaacetate monohydrate have been reported previously (Park & Shin, 1993) and the crystal structure of sucrose octaacetate has been studied (Oliver & Strickland, 1984). We now report the crystal structure of the α,α-trehalose octaacetate ethyl acetate solvate, (I) and base the stereochemistry of the molecule on the known absolute stereochemistry of trehalose.
No hydrogen bonds are present in (I). The substitution at C1/C1' is α,α, with C1—O1 = C1'—O1 = 1.416 (3) Å and C1—O1—C1' = 113.4 (2)°. 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 = 0.549 (2) Å, θ = 4.5 (3)°, ø = 14 (3)° (primed atoms) and Q = 0.563 (2) Å, θ = 4.3 (3)° and ø = 106 (4)° (unprimed atoms).