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The crystal structure of methyl 4-O-[beta]-L-fuco­pyran­osyl [alpha]-D-gluco­pyran­oside hemihydrate C13H24O10·0.5H2O is organized in sheets with antiparallel strands, where hydro­phobic interaction accounts for partial stabilization. Infinite hydrogen-bonding networks are observed within each layer as well as between layers; some of these hydrogen bonds are mediated by water mol­ecules. The conformation of the disaccharide is described by the glycosidic torsion angles: [varphi]H = -6.1° and [psi]H = 34.3°. The global energy minimum conformation as calculated by molecular mechanics in vacuo has [varphi]H = -58° and [psi]H = -20°. Thus, quite substantial changes are observed between the in vacuo structure and the crystal structure with its infinite hydrogen-bonding networks.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003589/os1102sup1.cif
Contains datablocks I, s4m3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003589/os1102Isup2.hkl
Contains datablock I

CCDC reference: 146063

Computing details top

Data collection: EXPOSE (Stoe, 1997); cell refinement: CELL (Stoe, 1997); data reduction: INTEGRATE (Stoe, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97; molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PLATON98 (Spek, 1998).

Methyl 4-O-β-L-fucopyranosyl α-D-glucopyranoside hemihydrate top
Crystal data top
C13H24O10·0.5H2OF(000) = 748
Mr = 349.33Dx = 1.461 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 23.343 (9) ÅCell parameters from 1078 reflections
b = 4.7027 (9) Åθ = 1.7–26.0°
c = 14.935 (6) ŵ = 0.13 mm1
β = 104.36 (5)°T = 293 K
V = 1588.2 (9) Å3Prism, colourless
Z = 40.20 × 0.15 × 0.10 mm
Data collection top
Stoe IPDS area detector
diffractometer
1358 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Graphite monochromatorθmax = 26.0°, θmin = 2.0°
Detector resolution: 6.0 pixels mm-1h = 2828
area detector scansk = 55
6288 measured reflectionsl = 1818
1751 independent reflections
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0521P)2]
where P = (Fo2 + 2Fc2)/3
1751 reflections(Δ/σ)max = 0.001
223 parametersΔρmax = 0.17 e Å3
1 restraintΔρmin = 0.17 e Å3
Special details top

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*/Ueq
C1f0.19708 (10)0.2939 (6)0.30442 (17)0.0253 (6)
H1f0.19740.50200.30080.030*
C2f0.17993 (10)0.2007 (7)0.39117 (17)0.0251 (6)
H2f0.17970.00750.39410.030*
C3f0.11824 (11)0.3134 (6)0.38785 (18)0.0264 (6)
H3f0.12060.52150.38740.032*
C4f0.07407 (11)0.2250 (6)0.29919 (19)0.0284 (6)
H4f0.03660.32480.29490.034*
C5f0.09797 (11)0.3057 (7)0.21687 (19)0.0304 (7)
H5f0.10180.51310.21540.037*
C6f0.05964 (14)0.2072 (11)0.1249 (2)0.0542 (10)
H6fA0.07660.27010.07600.081*
H6fB0.02070.28580.11610.081*
H6fC0.05730.00340.12430.081*
O2f0.21997 (9)0.3110 (5)0.47200 (14)0.0359 (5)
HO2f0.24350.18660.49560.054*
O3f0.09932 (9)0.2351 (5)0.46823 (14)0.0391 (5)
HO3f0.11080.07370.48400.059*
O4f0.06404 (9)0.0724 (5)0.29913 (16)0.0385 (5)
HO4f0.03290.10360.31340.058*
O5f0.15564 (7)0.1801 (5)0.22663 (12)0.0297 (5)
C1g0.39667 (12)0.5087 (7)0.2154 (2)0.0348 (7)
H1g0.42600.64890.20730.042*
C2g0.40512 (12)0.4536 (7)0.3176 (2)0.0323 (7)
H2g0.40360.63610.34860.039*
C3g0.35601 (11)0.2644 (7)0.33474 (17)0.0257 (6)
H3g0.35970.07410.31010.031*
C4g0.29561 (11)0.3871 (6)0.28777 (19)0.0252 (6)
H4g0.29010.56940.31630.030*
C5g0.29231 (12)0.4315 (7)0.18492 (19)0.0280 (6)
H5g0.29800.24880.15680.034*
C6g0.23579 (12)0.5693 (7)0.12934 (19)0.0334 (7)
H6gA0.20200.46500.13900.040*
H6gB0.23340.76250.15090.040*
C70.40587 (17)0.2884 (13)0.0779 (3)0.0713 (14)
H7A0.41310.10780.05280.107*
H7B0.43610.42040.07210.107*
H7C0.36800.35930.04470.107*
O1g0.40654 (9)0.2555 (6)0.17302 (16)0.0490 (6)
O2g0.46199 (9)0.3328 (7)0.35253 (18)0.0613 (8)
HO2g0.46270.24610.40040.092*
O3g0.36341 (9)0.2465 (5)0.43269 (12)0.0326 (5)
HO3g0.35690.08320.44670.049*
O4g0.25275 (7)0.1852 (4)0.30319 (13)0.0289 (4)
O5g0.33937 (8)0.6226 (5)0.17850 (13)0.0337 (5)
O6g0.23371 (10)0.5733 (5)0.03363 (14)0.0404 (5)
HO6g0.25050.71630.02160.061*
OW1/20.0123 (7)1/20.0406 (8)
HW0.5281 (18)0.093 (11)0.485 (3)0.075 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1f0.0199 (12)0.0298 (15)0.0261 (14)0.0019 (12)0.0053 (11)0.0008 (12)
C2f0.0237 (13)0.0235 (14)0.0259 (14)0.0013 (11)0.0019 (10)0.0017 (12)
C3f0.0299 (14)0.0265 (14)0.0254 (14)0.0035 (12)0.0114 (11)0.0018 (12)
C4f0.0215 (13)0.0263 (15)0.0379 (16)0.0023 (11)0.0085 (11)0.0000 (13)
C5f0.0233 (13)0.0389 (17)0.0274 (14)0.0002 (13)0.0032 (11)0.0017 (13)
C6f0.0424 (18)0.080 (3)0.0337 (18)0.003 (2)0.0019 (14)0.003 (2)
O2f0.0343 (11)0.0362 (12)0.0302 (11)0.0008 (10)0.0054 (8)0.0047 (9)
O3f0.0436 (12)0.0441 (13)0.0369 (11)0.0143 (11)0.0236 (9)0.0088 (11)
O4f0.0290 (11)0.0309 (11)0.0608 (14)0.0047 (9)0.0208 (10)0.0029 (12)
O5f0.0218 (9)0.0409 (12)0.0271 (10)0.0029 (9)0.0076 (7)0.0047 (9)
C1g0.0234 (15)0.0412 (19)0.0415 (18)0.0079 (13)0.0113 (13)0.0028 (14)
C2g0.0232 (14)0.0377 (17)0.0356 (16)0.0031 (13)0.0065 (12)0.0070 (14)
C3g0.0244 (13)0.0292 (14)0.0246 (13)0.0008 (12)0.0082 (10)0.0027 (12)
C4g0.0224 (13)0.0264 (14)0.0284 (14)0.0030 (11)0.0092 (11)0.0005 (12)
C5g0.0260 (14)0.0302 (15)0.0293 (15)0.0034 (12)0.0099 (11)0.0021 (13)
C6g0.0327 (15)0.0400 (17)0.0271 (16)0.0007 (14)0.0064 (12)0.0052 (14)
C70.057 (2)0.114 (4)0.050 (2)0.008 (3)0.0253 (18)0.021 (3)
O1g0.0415 (12)0.0584 (17)0.0533 (14)0.0050 (12)0.0238 (10)0.0040 (13)
O2g0.0210 (10)0.100 (2)0.0641 (16)0.0051 (12)0.0118 (10)0.0404 (16)
O3g0.0353 (10)0.0348 (12)0.0274 (10)0.0030 (10)0.0070 (8)0.0060 (9)
O4g0.0209 (9)0.0259 (10)0.0427 (11)0.0007 (8)0.0133 (8)0.0036 (10)
O5g0.0270 (10)0.0363 (12)0.0373 (11)0.0044 (9)0.0069 (8)0.0107 (10)
O6g0.0496 (13)0.0406 (13)0.0278 (11)0.0014 (11)0.0036 (9)0.0038 (10)
OW0.0285 (17)0.047 (2)0.051 (2)00.0198 (15)0
Geometric parameters (Å, º) top
C1f—O4g1.401 (3)C1g—H1g0.9800
C1f—O5f1.419 (3)C2g—O2g1.419 (4)
C1f—C2f1.513 (4)C2g—C3g1.522 (4)
C1f—H1f0.9800C2g—H2g0.9800
C2f—O2f1.428 (3)C3g—O3g1.432 (3)
C2f—C3f1.524 (4)C3g—C4g1.524 (4)
C2f—H2f0.9800C3g—H3g0.9800
C3f—O3f1.426 (3)C4g—O4g1.439 (3)
C3f—C4f1.520 (4)C4g—C5g1.533 (4)
C3f—H3f0.9800C4g—H4g0.9800
C4f—O4f1.418 (4)C5g—O5g1.441 (3)
C4f—C5f1.519 (4)C5g—C6g1.519 (4)
C4f—H4f0.9800C5g—H5g0.9800
C5f—O5f1.444 (3)C6g—O6g1.418 (4)
C5f—C6f1.514 (4)C6g—H6gA0.9700
C5f—H5f0.9800C6g—H6gB0.9700
C6f—H6fA0.9600C7—O1g1.426 (4)
C6f—H6fB0.9600C7—H7A0.9600
C6f—H6fC0.9600C7—H7B0.9600
O2f—HO2f0.8200C7—H7C0.9600
O3f—HO3f0.8200O2g—HO2g0.8200
O4f—HO4f0.8200O3g—HO3g0.8200
C1g—O1g1.394 (4)O6g—HO6g0.8200
C1g—O5g1.419 (4)OW—HW0.83 (4)
C1g—C2g1.513 (4)
O4g—C1f—O5f107.3 (2)O5g—C1g—H1g108.6
O4g—C1f—C2f110.4 (2)C2g—C1g—H1g108.6
O5f—C1f—C2f108.7 (2)O2g—C2g—C1g108.4 (2)
O4g—C1f—H1f110.1O2g—C2g—C3g112.3 (3)
O5f—C1f—H1f110.1C1g—C2g—C3g110.8 (2)
C2f—C1f—H1f110.1O2g—C2g—H2g108.4
O2f—C2f—C1f111.2 (2)C1g—C2g—H2g108.4
O2f—C2f—C3f108.4 (2)C3g—C2g—H2g108.4
C1f—C2f—C3f108.7 (2)O3g—C3g—C2g107.5 (2)
O2f—C2f—H2f109.5O3g—C3g—C4g110.8 (2)
C1f—C2f—H2f109.5C2g—C3g—C4g110.5 (2)
C3f—C2f—H2f109.5O3g—C3g—H3g109.3
O3f—C3f—C4f112.2 (2)C2g—C3g—H3g109.3
O3f—C3f—C2f111.7 (2)C4g—C3g—H3g109.3
C4f—C3f—C2f111.4 (2)O4g—C4g—C3g106.1 (2)
O3f—C3f—H3f107.1O4g—C4g—C5g112.7 (2)
C4f—C3f—H3f107.1C3g—C4g—C5g108.9 (2)
C2f—C3f—H3f107.1O4g—C4g—H4g109.7
O4f—C4f—C5f109.9 (2)C3g—C4g—H4g109.7
O4f—C4f—C3f110.3 (2)C5g—C4g—H4g109.7
C5f—C4f—C3f109.3 (2)O5g—C5g—C6g105.7 (2)
O4f—C4f—H4f109.1O5g—C5g—C4g107.6 (2)
C5f—C4f—H4f109.1C6g—C5g—C4g115.3 (2)
C3f—C4f—H4f109.1O5g—C5g—H5g109.4
O5f—C5f—C6f107.0 (2)C6g—C5g—H5g109.4
O5f—C5f—C4f109.7 (2)C4g—C5g—H5g109.4
C6f—C5f—C4f113.9 (2)O6g—C6g—C5g111.4 (2)
O5f—C5f—H5f108.7O6g—C6g—H6gA109.4
C6f—C5f—H5f108.7C5g—C6g—H6gA109.4
C4f—C5f—H5f108.7O6g—C6g—H6gB109.4
C5f—C6f—H6fA109.5C5g—C6g—H6gB109.4
C5f—C6f—H6fB109.5H6gA—C6g—H6gB108.0
H6fA—C6f—H6fB109.5O1g—C7—H7A109.5
C5f—C6f—H6fC109.5O1g—C7—H7B109.5
H6fA—C6f—H6fC109.5H7A—C7—H7B109.5
H6fB—C6f—H6fC109.5O1g—C7—H7C109.5
C2f—O2f—HO2f109.5H7A—C7—H7C109.5
C3f—O3f—HO3f109.5H7B—C7—H7C109.5
C4f—O4f—HO4f109.5C1g—O1g—C7113.4 (3)
C1f—O5f—C5f110.9 (2)C2g—O2g—HO2g109.5
O1g—C1g—O5g113.1 (3)C3g—O3g—HO3g109.5
O1g—C1g—C2g108.5 (3)C1f—O4g—C4g116.5 (2)
O5g—C1g—C2g109.3 (2)C1g—O5g—C5g113.5 (2)
O1g—C1g—H1g108.6C6g—O6g—HO6g109.5
O5f—C1f—O4g—C4g113.8 (2)O5g—C1g—O1g—C764.8 (3)
H1f—C1f—O4g—C4g6.1H1g—C1g—O1g—C755.9
C1f—O4g—C4g—C3g152.6 (2)C1f—O4g—C4g—C5g88.3 (3)
C1f—O4g—C4g—H4g34.3C2f—C1f—O4g—C4g127.9 (2)
O5g—C5g—C6g—O6g67.8 (3)C2g—C1g—O1g—C7173.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
OW—HW···O3fi0.83 (4)1.92 (4)2.749 (3)172 (5)
O6g—HO6g···O6gii0.821.952.738 (2)162
O3g—HO3g···O3fiii0.822.172.844 (3)140
O2g—HO2g···OW0.821.952.702 (3)152
O4f—HO4f···O2giv0.821.912.730 (3)177
O3f—HO3f···O3giii0.821.982.755 (3)158
O2f—HO2f···O2fiii0.821.972.759 (2)162
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y1/2, z+1; (iv) x1/2, y1/2, z.
 

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