Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107059756/sf3069sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270107059756/sf3069Isup2.hkl |
CCDC reference: 681532
The synthesis of (I) was described by Baumann et al. (1991). Suitable crystals was grown with the sitting-drop technique, in which the solvent was allowed to evaporate. F2G was dissolved in water to a concentration of 375 mg ml-1 and mixed with an equal amount of 20% PEG 400 in water at ambient temperature. Crystals formed after a few days and were mounted in capillaries. Data were collected on beamline I711 at the Swedish synchrotron radiation facility, MAXLAB, Lund.
The hydrogen atoms were geometrically placed and constrained to ride on the parent atom. The C—H bond distances are 0.98 Å for CH3, 0.99 Å for CH2, 1.00 Å for CH. The O—H bond distance is 0.84 Å for OH groups. The Uiso(H) = 1.5 Ueq(C,O) for the CH3 and OH while it was set to 1.2 Ueq(C) for all other H atoms. The value of the Flack parameter (Flack, 1983) was not meaningful due to the absence of significant anomalous scatterers, thus the data were merged using MERG 3 in SHELXL97. The H atoms of the water molecule were located from difference density map and the d(O—H) were restrained to retain the previously known geometry of the water molecule. The hydrogen atoms of the water molecule were given Uiso(H) = 1.5Ueq(O). The absolute configuration of each sugar residue is known from the starting compounds used in the synthesis.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Diamond (Bergerhoff, 1996); software used to prepare material for publication: PLATON (Spek,2003).
C13H24O10·H2O | F(000) = 384 |
Mr = 358.34 | Dx = 1.413 Mg m−3 |
Monoclinic, P21 | Synchrotron radiation, λ = 0.872 Å |
Hall symbol: P 2yb | Cell parameters from 4040 reflections |
a = 7.166 (2) Å | θ = 1.4–32.1° |
b = 6.3924 (16) Å | µ = 0.20 mm−1 |
c = 18.518 (4) Å | T = 100 K |
β = 96.876 (12)° | Block, colourless |
V = 842.1 (4) Å3 | 0.12 × 0.06 × 0.03 mm |
Z = 2 |
Smart 1K CCD diffractometer | 1751 independent reflections |
Radiation source: Beamline I711, Maxlab | 1726 reflections with I > 2σ(I) |
Silicon monochromator | Rint = 0.073 |
Detector resolution: 10 pixels mm-1 | θmax = 32.1°, θmin = 1.4° |
ω scan at different ϕ | h = −8→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −7→7 |
Tmin = 0.97, Tmax = 0.99 | l = −22→22 |
4040 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0958P)2 + 0.2168P] where P = (Fo2 + 2Fc2)/3 |
1751 reflections | (Δ/σ)max < 0.001 |
229 parameters | Δρmax = 0.27 e Å−3 |
4 restraints | Δρmin = −0.30 e Å−3 |
C13H24O10·H2O | V = 842.1 (4) Å3 |
Mr = 358.34 | Z = 2 |
Monoclinic, P21 | Synchrotron radiation, λ = 0.872 Å |
a = 7.166 (2) Å | µ = 0.20 mm−1 |
b = 6.3924 (16) Å | T = 100 K |
c = 18.518 (4) Å | 0.12 × 0.06 × 0.03 mm |
β = 96.876 (12)° |
Smart 1K CCD diffractometer | 1751 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 1726 reflections with I > 2σ(I) |
Tmin = 0.97, Tmax = 0.99 | Rint = 0.073 |
4040 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 4 restraints |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.27 e Å−3 |
1751 reflections | Δρmin = −0.30 e Å−3 |
229 parameters |
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 | ||
C1F | 0.6866 (4) | 0.5242 (5) | 0.82828 (13) | 0.0164 (6) | |
H1F | 0.7541 | 0.4015 | 0.8526 | 0.020* | |
C2F | 0.5415 (4) | 0.6075 (5) | 0.87476 (14) | 0.0166 (5) | |
H2F | 0.4801 | 0.7343 | 0.8508 | 0.020* | |
O2F | 0.3992 (3) | 0.4550 (4) | 0.88512 (10) | 0.0202 (4) | |
H2FA | 0.3120 | 0.4625 | 0.8506 | 0.030* | |
C3F | 0.6442 (4) | 0.6692 (5) | 0.94856 (14) | 0.0180 (6) | |
H3F | 0.7049 | 0.5415 | 0.9721 | 0.022* | |
O3F | 0.5090 (3) | 0.7437 (4) | 0.99226 (11) | 0.0197 (5) | |
H3FA | 0.5639 | 0.7908 | 1.0315 | 0.030* | |
C4F | 0.7986 (4) | 0.8299 (5) | 0.93802 (14) | 0.0195 (6) | |
H4F | 0.8762 | 0.8521 | 0.9860 | 0.023* | |
O4F | 0.7200 (3) | 1.0270 (4) | 0.91348 (11) | 0.0234 (5) | |
H4FA | 0.6418 | 1.0659 | 0.9411 | 0.035* | |
C5F | 0.9283 (4) | 0.7509 (5) | 0.88367 (14) | 0.0177 (6) | |
H5F | 0.9979 | 0.6258 | 0.9052 | 0.021* | |
C6F | 1.0709 (4) | 0.9101 (5) | 0.86421 (15) | 0.0210 (6) | |
H6FA | 1.1507 | 0.8466 | 0.8307 | 0.031* | |
H6FB | 1.1491 | 0.9553 | 0.9085 | 0.031* | |
H6FC | 1.0052 | 1.0312 | 0.8408 | 0.031* | |
O5F | 0.8173 (3) | 0.6873 (4) | 0.81700 (10) | 0.0187 (4) | |
C1G | 0.5949 (3) | 0.1173 (5) | 0.70603 (14) | 0.0155 (5) | |
H1G | 0.6078 | 0.0400 | 0.7533 | 0.019* | |
O1G | 0.4002 (3) | 0.1525 (3) | 0.68338 (10) | 0.0180 (4) | |
C7G | 0.2951 (4) | −0.0382 (5) | 0.67637 (15) | 0.0219 (6) | |
H7GA | 0.1631 | −0.0071 | 0.6597 | 0.033* | |
H7GB | 0.3042 | −0.1088 | 0.7236 | 0.033* | |
H7GC | 0.3461 | −0.1294 | 0.6410 | 0.033* | |
C2G | 0.6966 (4) | 0.3295 (4) | 0.71767 (14) | 0.0160 (5) | |
H2G | 0.8231 | 0.3045 | 0.7454 | 0.019* | |
O2G | 0.5932 (2) | 0.4649 (3) | 0.75958 (10) | 0.0165 (4) | |
C3G | 0.7239 (4) | 0.4418 (5) | 0.64713 (14) | 0.0189 (6) | |
H3G | 0.6020 | 0.5083 | 0.6274 | 0.023* | |
O3G | 0.8626 (3) | 0.6018 (4) | 0.66041 (10) | 0.0193 (4) | |
H3GA | 0.8174 | 0.7032 | 0.6814 | 0.029* | |
C4G | 0.7865 (4) | 0.2958 (5) | 0.58885 (14) | 0.0177 (6) | |
H4G | 0.9223 | 0.2598 | 0.6015 | 0.021* | |
O4G | 0.7615 (3) | 0.4042 (4) | 0.52147 (10) | 0.0200 (4) | |
H4GA | 0.8594 | 0.3934 | 0.5009 | 0.030* | |
C5G | 0.6690 (4) | 0.0952 (5) | 0.58384 (14) | 0.0163 (5) | |
H5G | 0.5347 | 0.1336 | 0.5687 | 0.020* | |
C6G | 0.7281 (4) | −0.0631 (5) | 0.53008 (14) | 0.0193 (6) | |
H6GA | 0.6467 | −0.1883 | 0.5301 | 0.023* | |
H6GB | 0.7102 | −0.0020 | 0.4806 | 0.023* | |
O6G | 0.9240 (3) | −0.1260 (3) | 0.54754 (10) | 0.0196 (4) | |
H6G | 0.9322 | −0.2163 | 0.5807 | 0.029* | |
O5G | 0.6813 (3) | −0.0032 (3) | 0.65409 (10) | 0.0171 (4) | |
OW | 0.1665 (3) | 0.4184 (4) | 0.75899 (11) | 0.0250 (5) | |
HW1 | 0.081 (4) | 0.506 (6) | 0.7297 (15) | 0.038* | |
HW2 | 0.239 (5) | 0.353 (6) | 0.7255 (14) | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1F | 0.0177 (12) | 0.0174 (14) | 0.0134 (11) | −0.0042 (12) | −0.0007 (9) | −0.0012 (11) |
C2F | 0.0180 (11) | 0.0162 (13) | 0.0163 (11) | −0.0016 (11) | 0.0051 (9) | 0.0014 (10) |
O2F | 0.0200 (9) | 0.0205 (11) | 0.0203 (9) | −0.0034 (9) | 0.0032 (7) | −0.0002 (8) |
C3F | 0.0196 (12) | 0.0177 (13) | 0.0179 (12) | 0.0016 (11) | 0.0073 (10) | −0.0010 (11) |
O3F | 0.0230 (9) | 0.0206 (12) | 0.0165 (9) | −0.0011 (8) | 0.0070 (7) | −0.0016 (9) |
C4F | 0.0200 (12) | 0.0182 (14) | 0.0206 (13) | 0.0040 (11) | 0.0031 (10) | −0.0003 (12) |
O4F | 0.0285 (11) | 0.0158 (11) | 0.0281 (10) | 0.0026 (9) | 0.0118 (8) | 0.0030 (8) |
C5F | 0.0190 (12) | 0.0180 (14) | 0.0162 (11) | −0.0005 (12) | 0.0029 (10) | −0.0010 (12) |
C6F | 0.0202 (12) | 0.0200 (15) | 0.0237 (13) | −0.0022 (13) | 0.0064 (10) | 0.0000 (12) |
O5F | 0.0193 (9) | 0.0194 (11) | 0.0175 (9) | −0.0029 (9) | 0.0032 (7) | −0.0013 (8) |
C1G | 0.0132 (11) | 0.0155 (14) | 0.0190 (11) | 0.0008 (11) | 0.0059 (9) | −0.0008 (11) |
O1G | 0.0161 (9) | 0.0154 (11) | 0.0224 (9) | 0.0010 (8) | 0.0014 (7) | −0.0015 (8) |
C7G | 0.0213 (13) | 0.0212 (15) | 0.0235 (13) | −0.0029 (12) | 0.0031 (11) | −0.0018 (12) |
C2G | 0.0172 (11) | 0.0124 (13) | 0.0189 (12) | 0.0004 (11) | 0.0043 (9) | −0.0041 (11) |
O2G | 0.0193 (8) | 0.0155 (10) | 0.0154 (8) | 0.0019 (8) | 0.0046 (7) | −0.0033 (8) |
C3G | 0.0169 (12) | 0.0223 (15) | 0.0178 (12) | −0.0004 (12) | 0.0034 (9) | −0.0008 (12) |
O3G | 0.0222 (9) | 0.0158 (10) | 0.0206 (9) | −0.0017 (8) | 0.0059 (7) | −0.0031 (8) |
C4G | 0.0225 (13) | 0.0127 (14) | 0.0182 (12) | −0.0008 (11) | 0.0040 (10) | −0.0004 (10) |
O4G | 0.0242 (10) | 0.0198 (11) | 0.0170 (9) | 0.0014 (9) | 0.0060 (7) | 0.0032 (9) |
C5G | 0.0192 (11) | 0.0161 (13) | 0.0139 (11) | 0.0024 (11) | 0.0028 (9) | 0.0002 (11) |
C6G | 0.0225 (13) | 0.0179 (14) | 0.0180 (12) | 0.0021 (13) | 0.0043 (10) | −0.0023 (12) |
O6G | 0.0221 (9) | 0.0153 (11) | 0.0221 (9) | 0.0005 (8) | 0.0058 (7) | 0.0000 (8) |
O5G | 0.0206 (9) | 0.0160 (10) | 0.0151 (9) | 0.0003 (8) | 0.0034 (7) | −0.0014 (8) |
OW | 0.0188 (9) | 0.0315 (13) | 0.0246 (10) | 0.0059 (10) | 0.0017 (8) | −0.0016 (10) |
C1F—O2G | 1.416 (3) | O1G—C7G | 1.430 (4) |
C1F—O5F | 1.434 (4) | C7G—H7GA | 0.9800 |
C1F—C2F | 1.523 (4) | C7G—H7GB | 0.9800 |
C1F—H1F | 1.0000 | C7G—H7GC | 0.9800 |
C2F—O2F | 1.440 (3) | C2G—O2G | 1.428 (3) |
C2F—C3F | 1.525 (4) | C2G—C3G | 1.523 (4) |
C2F—H2F | 1.0000 | C2G—H2G | 1.0000 |
O2F—H2FA | 0.8400 | C3G—O3G | 1.427 (4) |
C3F—O3F | 1.417 (3) | C3G—C4G | 1.534 (4) |
C3F—C4F | 1.540 (4) | C3G—H3G | 1.0000 |
C3F—H3F | 1.0000 | O3G—H3GA | 0.8400 |
O3F—H3FA | 0.8400 | C4G—O4G | 1.420 (3) |
C4F—O4F | 1.432 (4) | C4G—C5G | 1.531 (4) |
C4F—C5F | 1.535 (4) | C4G—H4G | 1.0000 |
C4F—H4F | 1.0000 | O4G—H4GA | 0.8400 |
O4F—H4FA | 0.8400 | C5G—O5G | 1.438 (3) |
C5F—O5F | 1.445 (3) | C5G—C6G | 1.515 (4) |
C5F—C6F | 1.516 (4) | C5G—H5G | 1.0000 |
C5F—H5F | 1.0000 | C6G—O6G | 1.458 (3) |
C6F—H6FA | 0.9800 | C6G—H6GA | 0.9900 |
C6F—H6FB | 0.9800 | C6G—H6GB | 0.9900 |
C6F—H6FC | 0.9800 | O6G—H6G | 0.8400 |
C1G—O1G | 1.426 (3) | OW—HW1 | 0.950 (10) |
C1G—O5G | 1.430 (3) | OW—HW2 | 0.950 (10) |
C1G—C2G | 1.543 (4) | H1f—H2g | 2.19 |
C1G—H1G | 1.0000 | ||
O2G—C1F—O5F | 108.1 (2) | C2G—C1G—H1G | 108.7 |
O2G—C1F—C2F | 108.7 (2) | C1G—O1G—C7G | 112.2 (2) |
O5F—C1F—C2F | 109.3 (2) | O1G—C7G—H7GA | 109.5 |
O2G—C1F—H1F | 110.3 | O1G—C7G—H7GB | 109.5 |
O5F—C1F—H1F | 110.3 | H7GA—C7G—H7GB | 109.5 |
C2F—C1F—H1F | 110.3 | O1G—C7G—H7GC | 109.5 |
O2F—C2F—C1F | 112.4 (2) | H7GA—C7G—H7GC | 109.5 |
O2F—C2F—C3F | 109.2 (2) | H7GB—C7G—H7GC | 109.5 |
C1F—C2F—C3F | 107.9 (2) | O2G—C2G—C3G | 108.0 (2) |
O2F—C2F—H2F | 109.1 | O2G—C2G—C1G | 110.0 (2) |
C1F—C2F—H2F | 109.1 | C3G—C2G—C1G | 113.7 (2) |
C3F—C2F—H2F | 109.1 | O2G—C2G—H2G | 108.4 |
C2F—O2F—H2FA | 109.5 | C3G—C2G—H2G | 108.4 |
O3F—C3F—C2F | 108.0 (2) | C1G—C2G—H2G | 108.4 |
O3F—C3F—C4F | 113.5 (3) | C1F—O2G—C2G | 115.5 (2) |
C2F—C3F—C4F | 109.6 (2) | O3G—C3G—C2G | 110.4 (2) |
O3F—C3F—H3F | 108.5 | O3G—C3G—C4G | 107.5 (2) |
C2F—C3F—H3F | 108.5 | C2G—C3G—C4G | 113.3 (3) |
C4F—C3F—H3F | 108.5 | O3G—C3G—H3G | 108.5 |
C3F—O3F—H3FA | 109.5 | C2G—C3G—H3G | 108.5 |
O4F—C4F—C5F | 109.1 (2) | C4G—C3G—H3G | 108.5 |
O4F—C4F—C3F | 111.5 (2) | C3G—O3G—H3GA | 109.5 |
C5F—C4F—C3F | 111.4 (2) | O4G—C4G—C5G | 110.2 (2) |
O4F—C4F—H4F | 108.3 | O4G—C4G—C3G | 107.7 (2) |
C5F—C4F—H4F | 108.3 | C5G—C4G—C3G | 110.3 (2) |
C3F—C4F—H4F | 108.3 | O4G—C4G—H4G | 109.5 |
C4F—O4F—H4FA | 109.5 | C5G—C4G—H4G | 109.5 |
O5F—C5F—C6F | 107.7 (2) | C3G—C4G—H4G | 109.5 |
O5F—C5F—C4F | 109.8 (2) | C4G—O4G—H4GA | 109.5 |
C6F—C5F—C4F | 114.4 (3) | O5G—C5G—C6G | 108.1 (2) |
O5F—C5F—H5F | 108.3 | O5G—C5G—C4G | 109.7 (2) |
C6F—C5F—H5F | 108.3 | C6G—C5G—C4G | 113.8 (2) |
C4F—C5F—H5F | 108.3 | O5G—C5G—H5G | 108.3 |
C5F—C6F—H6FA | 109.5 | C6G—C5G—H5G | 108.3 |
C5F—C6F—H6FB | 109.5 | C4G—C5G—H5G | 108.3 |
H6FA—C6F—H6FB | 109.5 | O6G—C6G—C5G | 112.1 (2) |
C5F—C6F—H6FC | 109.5 | O6G—C6G—H6GA | 109.2 |
H6FA—C6F—H6FC | 109.5 | C5G—C6G—H6GA | 109.2 |
H6FB—C6F—H6FC | 109.5 | O6G—C6G—H6GB | 109.2 |
C1F—O5F—C5F | 112.5 (2) | C5G—C6G—H6GB | 109.2 |
O1G—C1G—O5G | 112.0 (2) | H6GA—C6G—H6GB | 107.9 |
O1G—C1G—C2G | 109.4 (2) | C6G—O6G—H6G | 109.5 |
O5G—C1G—C2G | 109.41 (19) | C1G—O5G—C5G | 112.8 (2) |
O1G—C1G—H1G | 108.7 | HW1—OW—HW2 | 104.5 (14) |
O5G—C1G—H1G | 108.7 | ||
O2G—C1F—C2F—O2F | 59.2 (3) | O5F—C1F—O2G—C2G | 79.1 (3) |
O5F—C1F—C2F—O2F | 176.9 (2) | C2F—C1F—O2G—C2G | −162.4 (2) |
O2G—C1F—C2F—C3F | 179.6 (2) | C3G—C2G—O2G—C1F | −119.0 (2) |
O5F—C1F—C2F—C3F | −62.6 (3) | C1G—C2G—O2G—C1F | 116.5 (2) |
O2F—C2F—C3F—O3F | −56.6 (3) | O2G—C2G—C3G—O3G | 74.4 (3) |
C1F—C2F—C3F—O3F | −179.1 (2) | C1G—C2G—C3G—O3G | −163.3 (2) |
O2F—C2F—C3F—C4F | 179.2 (2) | O2G—C2G—C3G—C4G | −165.0 (2) |
C1F—C2F—C3F—C4F | 56.7 (3) | C1G—C2G—C3G—C4G | −42.7 (3) |
O3F—C3F—C4F—O4F | −51.6 (3) | O3G—C3G—C4G—O4G | −72.2 (3) |
C2F—C3F—C4F—O4F | 69.3 (3) | C2G—C3G—C4G—O4G | 165.6 (2) |
O3F—C3F—C4F—C5F | −173.7 (2) | O3G—C3G—C4G—C5G | 167.5 (2) |
C2F—C3F—C4F—C5F | −52.8 (3) | C2G—C3G—C4G—C5G | 45.3 (3) |
O4F—C4F—C5F—O5F | −71.0 (3) | O4G—C4G—C5G—O5G | −174.6 (2) |
C3F—C4F—C5F—O5F | 52.5 (3) | C3G—C4G—C5G—O5G | −55.8 (3) |
O4F—C4F—C5F—C6F | 50.2 (3) | O4G—C4G—C5G—C6G | 64.1 (3) |
C3F—C4F—C5F—C6F | 173.7 (2) | C3G—C4G—C5G—C6G | −177.1 (2) |
O2G—C1F—O5F—C5F | −176.6 (2) | O5G—C5G—C6G—O6G | −63.6 (3) |
C2F—C1F—O5F—C5F | 65.3 (3) | C4G—C5G—C6G—O6G | 58.5 (3) |
C6F—C5F—O5F—C1F | 175.5 (2) | O1G—C1G—O5G—C5G | 59.6 (3) |
C4F—C5F—O5F—C1F | −59.3 (3) | C2G—C1G—O5G—C5G | −61.8 (3) |
O5G—C1G—O1G—C7G | 62.5 (3) | C6G—C5G—O5G—C1G | −168.7 (2) |
C2G—C1G—O1G—C7G | −176.0 (2) | C4G—C5G—O5G—C1G | 66.7 (3) |
O1G—C1G—C2G—O2G | 47.2 (3) | C1F—O2G—C2G—H2G | −1.8 |
O5G—C1G—C2G—O2G | 170.2 (2) | H1F—C1F—O2G—C2G | −41.5 |
O1G—C1G—C2G—C3G | −74.0 (3) | C7G—O1G—C1G—H1G | −57.5 |
O5G—C1G—C2G—C3G | 49.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2f—H2fA···OW | 0.84 | 1.90 | 2.712 (3) | 162 |
O3f—H3fA···O2fi | 0.84 | 1.86 | 2.657 (3) | 158 |
O4f—H4fA···O3fi | 0.84 | 2.07 | 2.888 (3) | 163 |
O3g—H3gA···O5gii | 0.84 | 2.15 | 2.835 (3) | 139 |
O3g—H3gA···O5f | 0.84 | 2.51 | 3.006 (3) | 118 |
O4g—H4gA···O6giii | 0.84 | 1.89 | 2.728 (3) | 178 |
O6g—H6g···O3giv | 0.84 | 1.99 | 2.795 (3) | 160 |
OW—HW1···O3gv | 0.95 (5) | 2.00 (5) | 2.915 (3) | 161 (3) |
OW—HW2···O1g | 0.95 (5) | 1.95 (5) | 2.866 (3) | 161 (3) |
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) x, y+1, z; (iii) −x+2, y+1/2, −z+1; (iv) x, y−1, z; (v) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C13H24O10·H2O |
Mr | 358.34 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 100 |
a, b, c (Å) | 7.166 (2), 6.3924 (16), 18.518 (4) |
β (°) | 96.876 (12) |
V (Å3) | 842.1 (4) |
Z | 2 |
Radiation type | Synchrotron, λ = 0.872 Å |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.12 × 0.06 × 0.03 |
Data collection | |
Diffractometer | Smart 1K CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2002) |
Tmin, Tmax | 0.97, 0.99 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4040, 1751, 1726 |
Rint | 0.073 |
(sin θ/λ)max (Å−1) | 0.610 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.120, 1.07 |
No. of reflections | 1751 |
No. of parameters | 229 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.30 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), Diamond (Bergerhoff, 1996), PLATON (Spek,2003).
H1f—H2g | 2.19 | ||
O5G—C1G—O1G—C7G | 62.5 (3) | O5G—C5G—C6G—O6G | −63.6 (3) |
C2G—C1G—O1G—C7G | −176.0 (2) | C1F—O2G—C2G—H2G | −1.8 |
O5F—C1F—O2G—C2G | 79.1 (3) | H1F—C1F—O2G—C2G | −41.5 |
C3G—C2G—O2G—C1F | −119.0 (2) | C7G—O1G—C1G—H1G | −57.5 |
C1G—C2G—O2G—C1F | 116.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2f—H2fA···OW | 0.84 | 1.903 | 2.712 (3) | 162 |
O3f—H3fA···O2fi | 0.84 | 1.859 | 2.657 (3) | 158 |
O4f—H4fA···O3fi | 0.84 | 2.074 | 2.888 (3) | 163 |
O3g—H3gA···O5gii | 0.84 | 2.147 | 2.835 (3) | 139 |
O3g—H3gA···O5f | 0.84 | 2.514 | 3.006 (3) | 118 |
O4g—H4gA···O6giii | 0.84 | 1.888 | 2.728 (3) | 178 |
O6g—H6g···O3giv | 0.84 | 1.989 | 2.795 (3) | 160 |
OW—HW1···O3gv | 0.95 (5) | 2.00 (5) | 2.915 (3) | 161 (3) |
OW—HW2···O1g | 0.95 (5) | 1.95 (5) | 2.866 (3) | 161 (3) |
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) x, y+1, z; (iii) −x+2, y+1/2, −z+1; (iv) x, y−1, z; (v) x−1, y, z. |
Carbohydrates are often found as glycoconjugates in nature and they are involved in a multitude of different functions of significant importance in biomolecular systems (Carlsson et al., 2007). Elucidation of the three-dimensional structure of the carbohydrate part or of substructures of a larger oligosaccharide may reveal structural features including possible epitopes essential for molecular recognition events. We have previously reported the crystal structures of methyl 4-O-β-L-fucopyranosyl α-D-glucopyranoside (F4G) (Eriksson et al., 2000) and methyl 3-O-β-L-fucopyranosyl α-D-glucopyranoside (F3G) (Färnbäck et al., 2003) as a hemihydrate and a trihydrate, respectively, and we report here the title compound (F2G) as a monohydrate.
In F4G, the glycosidic torsion angles are ϕH = -6° (being unusual since it was close to an eclipsed conformation) and ψH = 34°, whereas in F3G, the values are ϕH = -38° and ψH = 18°. The hydroxymethyl group for the exocyclic torsion angle ω revealed the gt and gg conformations in F4G and F3G, respectively. Both conformations are favored by the gauche effect and in none of the compounds is a 1,3-syn-diaxial interaction to O4 present, consistent with the Hassel–Ottar effect (Jeffrey, 1990). Notably, both conformations are shifted slightly from the ideal gauche conformation, i.e. ω = 68° in the former and ω = -66° in the latter compound. In F3G, an intramolecular hydrogen bond was present, with O2g as the donor atom and O5f as the acceptor atom.
In the present study, the torsion angles at the glycosidic linkage of the title disaccharide F2G are ϕH = -41° and ψH = -2°. The exocyclic torsion angle ω is -64°, i.e. the gg conformation. The calculated Cremer & Pople (1975) parameters show that the fucose ring is close to the expected chair conformation, i.e. 1C4, and that the glucose ring has the anticipated 4C1 conformation. The parameters for the fucose ring are Q = 0.592 (3) Å, θ = 173.1 (3)° and ϕ = 256 (3)°, and those for the glucose ring Q = 0.544 (3) Å, θ = 12.1 (3)° and ϕ = 338 (2)°. An internal hydrogen bond is present, with atom O5f as the acceptor and atom O3g as the donor (cf. F3G where O5f is the acceptor and O2g the donor), adjacent to the glycosidic linkage (Fig. 1). On the other side, the water molecule present in the crystal structure confers additional structure to F2G. The water molecule is positioned in such a way that atom O2f acts as a donor with its hydroxy H atom pointing towards the water O atom, and both water H atoms act as donors, to atoms O1g and O3g, in a neighbouring molecule at (x + 1, y, z). Further details about the hydrogen bonding are shown in Fig. 2 and Table 2. Thus, the water molecule is present as a bridge between atoms O2f and O1g. Bridging water molecules of structural importance have been reported to be present in disaccharides using molecular dynamics simulations (Naidoo & Brady, 1999) and NMR spectroscopy (Sheng & van Halbeek, 1995). As a result of the intramolecular hydrogen-bonding pattern in the crystal structure of F2G, it is surmised that the disaccharide may be exceptionally well structured in aqueous solution, a matter that remains to be investigated.