Methyl 4-O-[beta]-L-fucopyranosyl [alpha]-­D-­glucopyranoside hemihydrate

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.

Computing details

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

Crystal data

C13H24O10·0.5H2O	F(000) = 748
Mr = 349.33	Dx = 1.461 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 23.343 (9) Å	Cell parameters from 1078 reflections
b = 4.7027 (9) Å	θ = 1.7–26.0°
c = 14.935 (6) Å	µ = 0.13 mm^−1
β = 104.36 (5)°	T = 293 K
V = 1588.2 (9) Å^3	Prism, colourless
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection

Stoe IPDS area detector diffractometer	1358 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
Graphite monochromator	θmax = 26.0°, θmin = 2.0°
Detector resolution: 6.0 pixels mm^-1	h = −28→28
area detector scans	k = −5→5
6288 measured reflections	l = −18→18
1751 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0521P)^2] where P = (Fo^2 + 2Fc^2)/3
1751 reflections	(Δ/σ)max = 0.001
223 parameters	Δρmax = 0.17 e Å^−3
1 restraint	Δρmin = −0.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1f	0.19708 (10)	0.2939 (6)	0.30442 (17)	0.0253 (6)
H1f	0.1974	0.5020	0.3008	0.030*
C2f	0.17993 (10)	0.2007 (7)	0.39117 (17)	0.0251 (6)
H2f	0.1797	−0.0075	0.3941	0.030*
C3f	0.11824 (11)	0.3134 (6)	0.38785 (18)	0.0264 (6)
H3f	0.1206	0.5215	0.3874	0.032*
C4f	0.07407 (11)	0.2250 (6)	0.29919 (19)	0.0284 (6)
H4f	0.0366	0.3248	0.2949	0.034*
C5f	0.09797 (11)	0.3057 (7)	0.21687 (19)	0.0304 (7)
H5f	0.1018	0.5131	0.2154	0.037*
C6f	0.05964 (14)	0.2072 (11)	0.1249 (2)	0.0542 (10)
H6fA	0.0766	0.2701	0.0760	0.081*
H6fB	0.0207	0.2858	0.1161	0.081*
H6fC	0.0573	0.0034	0.1243	0.081*
O2f	0.21997 (9)	0.3110 (5)	0.47200 (14)	0.0359 (5)
HO2f	0.2435	0.1866	0.4956	0.054*
O3f	0.09932 (9)	0.2351 (5)	0.46823 (14)	0.0391 (5)
HO3f	0.1108	0.0737	0.4840	0.059*
O4f	0.06404 (9)	−0.0724 (5)	0.29913 (16)	0.0385 (5)
HO4f	0.0329	−0.1036	0.3134	0.058*
O5f	0.15564 (7)	0.1801 (5)	0.22663 (12)	0.0297 (5)
C1g	0.39667 (12)	0.5087 (7)	0.2154 (2)	0.0348 (7)
H1g	0.4260	0.6489	0.2073	0.042*
C2g	0.40512 (12)	0.4536 (7)	0.3176 (2)	0.0323 (7)
H2g	0.4036	0.6361	0.3486	0.039*
C3g	0.35601 (11)	0.2644 (7)	0.33474 (17)	0.0257 (6)
H3g	0.3597	0.0741	0.3101	0.031*
C4g	0.29561 (11)	0.3871 (6)	0.28777 (19)	0.0252 (6)
H4g	0.2901	0.5694	0.3163	0.030*
C5g	0.29231 (12)	0.4315 (7)	0.18492 (19)	0.0280 (6)
H5g	0.2980	0.2488	0.1568	0.034*
C6g	0.23579 (12)	0.5693 (7)	0.12934 (19)	0.0334 (7)
H6gA	0.2020	0.4650	0.1390	0.040*
H6gB	0.2334	0.7625	0.1509	0.040*
C7	0.40587 (17)	0.2884 (13)	0.0779 (3)	0.0713 (14)
H7A	0.4131	0.1078	0.0528	0.107*
H7B	0.4361	0.4204	0.0721	0.107*
H7C	0.3680	0.3593	0.0447	0.107*
O1g	0.40654 (9)	0.2555 (6)	0.17302 (16)	0.0490 (6)
O2g	0.46199 (9)	0.3328 (7)	0.35253 (18)	0.0613 (8)
HO2g	0.4627	0.2461	0.4004	0.092*
O3g	0.36341 (9)	0.2465 (5)	0.43269 (12)	0.0326 (5)
HO3g	0.3569	0.0832	0.4467	0.049*
O4g	0.25275 (7)	0.1852 (4)	0.30319 (13)	0.0289 (4)
O5g	0.33937 (8)	0.6226 (5)	0.17850 (13)	0.0337 (5)
O6g	0.23371 (10)	0.5733 (5)	0.03363 (14)	0.0404 (5)
HO6g	0.2505	0.7163	0.0216	0.061*
OW	1/2	−0.0123 (7)	1/2	0.0406 (8)
HW	0.5281 (18)	−0.093 (11)	0.485 (3)	0.075 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1f	0.0199 (12)	0.0298 (15)	0.0261 (14)	−0.0019 (12)	0.0053 (11)	−0.0008 (12)
C2f	0.0237 (13)	0.0235 (14)	0.0259 (14)	−0.0013 (11)	0.0019 (10)	−0.0017 (12)
C3f	0.0299 (14)	0.0265 (14)	0.0254 (14)	0.0035 (12)	0.0114 (11)	0.0018 (12)
C4f	0.0215 (13)	0.0263 (15)	0.0379 (16)	0.0023 (11)	0.0085 (11)	0.0000 (13)
C5f	0.0233 (13)	0.0389 (17)	0.0274 (14)	−0.0002 (13)	0.0032 (11)	0.0017 (13)
C6f	0.0424 (18)	0.080 (3)	0.0337 (18)	−0.003 (2)	−0.0019 (14)	−0.003 (2)
O2f	0.0343 (11)	0.0362 (12)	0.0302 (11)	0.0008 (10)	−0.0054 (8)	−0.0047 (9)
O3f	0.0436 (12)	0.0441 (13)	0.0369 (11)	0.0143 (11)	0.0236 (9)	0.0088 (11)
O4f	0.0290 (11)	0.0309 (11)	0.0608 (14)	−0.0047 (9)	0.0208 (10)	−0.0029 (12)
O5f	0.0218 (9)	0.0409 (12)	0.0271 (10)	−0.0029 (9)	0.0076 (7)	−0.0047 (9)
C1g	0.0234 (15)	0.0412 (19)	0.0415 (18)	−0.0079 (13)	0.0113 (13)	0.0028 (14)
C2g	0.0232 (14)	0.0377 (17)	0.0356 (16)	−0.0031 (13)	0.0065 (12)	0.0070 (14)
C3g	0.0244 (13)	0.0292 (14)	0.0246 (13)	−0.0008 (12)	0.0082 (10)	0.0027 (12)
C4g	0.0224 (13)	0.0264 (14)	0.0284 (14)	−0.0030 (11)	0.0092 (11)	0.0005 (12)
C5g	0.0260 (14)	0.0302 (15)	0.0293 (15)	−0.0034 (12)	0.0099 (11)	0.0021 (13)
C6g	0.0327 (15)	0.0400 (17)	0.0271 (16)	0.0007 (14)	0.0064 (12)	0.0052 (14)
C7	0.057 (2)	0.114 (4)	0.050 (2)	−0.008 (3)	0.0253 (18)	−0.021 (3)
O1g	0.0415 (12)	0.0584 (17)	0.0533 (14)	0.0050 (12)	0.0238 (10)	−0.0040 (13)
O2g	0.0210 (10)	0.100 (2)	0.0641 (16)	0.0051 (12)	0.0118 (10)	0.0404 (16)
O3g	0.0353 (10)	0.0348 (12)	0.0274 (10)	−0.0030 (10)	0.0070 (8)	0.0060 (9)
O4g	0.0209 (9)	0.0259 (10)	0.0427 (11)	−0.0007 (8)	0.0133 (8)	0.0036 (10)
O5g	0.0270 (10)	0.0363 (12)	0.0373 (11)	−0.0044 (9)	0.0069 (8)	0.0107 (10)
O6g	0.0496 (13)	0.0406 (13)	0.0278 (11)	−0.0014 (11)	0.0036 (9)	0.0038 (10)
OW	0.0285 (17)	0.047 (2)	0.051 (2)	0	0.0198 (15)	0

Geometric parameters (Å, º)

C1f—O4g	1.401 (3)	C1g—H1g	0.9800
C1f—O5f	1.419 (3)	C2g—O2g	1.419 (4)
C1f—C2f	1.513 (4)	C2g—C3g	1.522 (4)
C1f—H1f	0.9800	C2g—H2g	0.9800
C2f—O2f	1.428 (3)	C3g—O3g	1.432 (3)
C2f—C3f	1.524 (4)	C3g—C4g	1.524 (4)
C2f—H2f	0.9800	C3g—H3g	0.9800
C3f—O3f	1.426 (3)	C4g—O4g	1.439 (3)
C3f—C4f	1.520 (4)	C4g—C5g	1.533 (4)
C3f—H3f	0.9800	C4g—H4g	0.9800
C4f—O4f	1.418 (4)	C5g—O5g	1.441 (3)
C4f—C5f	1.519 (4)	C5g—C6g	1.519 (4)
C4f—H4f	0.9800	C5g—H5g	0.9800
C5f—O5f	1.444 (3)	C6g—O6g	1.418 (4)
C5f—C6f	1.514 (4)	C6g—H6gA	0.9700
C5f—H5f	0.9800	C6g—H6gB	0.9700
C6f—H6fA	0.9600	C7—O1g	1.426 (4)
C6f—H6fB	0.9600	C7—H7A	0.9600
C6f—H6fC	0.9600	C7—H7B	0.9600
O2f—HO2f	0.8200	C7—H7C	0.9600
O3f—HO3f	0.8200	O2g—HO2g	0.8200
O4f—HO4f	0.8200	O3g—HO3g	0.8200
C1g—O1g	1.394 (4)	O6g—HO6g	0.8200
C1g—O5g	1.419 (4)	OW—HW	0.83 (4)
C1g—C2g	1.513 (4)
O4g—C1f—O5f	107.3 (2)	O5g—C1g—H1g	108.6
O4g—C1f—C2f	110.4 (2)	C2g—C1g—H1g	108.6
O5f—C1f—C2f	108.7 (2)	O2g—C2g—C1g	108.4 (2)
O4g—C1f—H1f	110.1	O2g—C2g—C3g	112.3 (3)
O5f—C1f—H1f	110.1	C1g—C2g—C3g	110.8 (2)
C2f—C1f—H1f	110.1	O2g—C2g—H2g	108.4
O2f—C2f—C1f	111.2 (2)	C1g—C2g—H2g	108.4
O2f—C2f—C3f	108.4 (2)	C3g—C2g—H2g	108.4
C1f—C2f—C3f	108.7 (2)	O3g—C3g—C2g	107.5 (2)
O2f—C2f—H2f	109.5	O3g—C3g—C4g	110.8 (2)
C1f—C2f—H2f	109.5	C2g—C3g—C4g	110.5 (2)
C3f—C2f—H2f	109.5	O3g—C3g—H3g	109.3
O3f—C3f—C4f	112.2 (2)	C2g—C3g—H3g	109.3
O3f—C3f—C2f	111.7 (2)	C4g—C3g—H3g	109.3
C4f—C3f—C2f	111.4 (2)	O4g—C4g—C3g	106.1 (2)
O3f—C3f—H3f	107.1	O4g—C4g—C5g	112.7 (2)
C4f—C3f—H3f	107.1	C3g—C4g—C5g	108.9 (2)
C2f—C3f—H3f	107.1	O4g—C4g—H4g	109.7
O4f—C4f—C5f	109.9 (2)	C3g—C4g—H4g	109.7
O4f—C4f—C3f	110.3 (2)	C5g—C4g—H4g	109.7
C5f—C4f—C3f	109.3 (2)	O5g—C5g—C6g	105.7 (2)
O4f—C4f—H4f	109.1	O5g—C5g—C4g	107.6 (2)
C5f—C4f—H4f	109.1	C6g—C5g—C4g	115.3 (2)
C3f—C4f—H4f	109.1	O5g—C5g—H5g	109.4
O5f—C5f—C6f	107.0 (2)	C6g—C5g—H5g	109.4
O5f—C5f—C4f	109.7 (2)	C4g—C5g—H5g	109.4
C6f—C5f—C4f	113.9 (2)	O6g—C6g—C5g	111.4 (2)
O5f—C5f—H5f	108.7	O6g—C6g—H6gA	109.4
C6f—C5f—H5f	108.7	C5g—C6g—H6gA	109.4
C4f—C5f—H5f	108.7	O6g—C6g—H6gB	109.4
C5f—C6f—H6fA	109.5	C5g—C6g—H6gB	109.4
C5f—C6f—H6fB	109.5	H6gA—C6g—H6gB	108.0
H6fA—C6f—H6fB	109.5	O1g—C7—H7A	109.5
C5f—C6f—H6fC	109.5	O1g—C7—H7B	109.5
H6fA—C6f—H6fC	109.5	H7A—C7—H7B	109.5
H6fB—C6f—H6fC	109.5	O1g—C7—H7C	109.5
C2f—O2f—HO2f	109.5	H7A—C7—H7C	109.5
C3f—O3f—HO3f	109.5	H7B—C7—H7C	109.5
C4f—O4f—HO4f	109.5	C1g—O1g—C7	113.4 (3)
C1f—O5f—C5f	110.9 (2)	C2g—O2g—HO2g	109.5
O1g—C1g—O5g	113.1 (3)	C3g—O3g—HO3g	109.5
O1g—C1g—C2g	108.5 (3)	C1f—O4g—C4g	116.5 (2)
O5g—C1g—C2g	109.3 (2)	C1g—O5g—C5g	113.5 (2)
O1g—C1g—H1g	108.6	C6g—O6g—HO6g	109.5
O5f—C1f—O4g—C4g	113.8 (2)	O5g—C1g—O1g—C7	64.8 (3)
H1f—C1f—O4g—C4g	−6.1	H1g—C1g—O1g—C7	−55.9
C1f—O4g—C4g—C3g	152.6 (2)	C1f—O4g—C4g—C5g	−88.3 (3)
C1f—O4g—C4g—H4g	34.3	C2f—C1f—O4g—C4g	−127.9 (2)
O5g—C5g—C6g—O6g	67.8 (3)	C2g—C1g—O1g—C7	−173.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
OW—HW···O3f^i	0.83 (4)	1.92 (4)	2.749 (3)	172 (5)
O6g—HO6g···O6g^ii	0.82	1.95	2.738 (2)	162
O3g—HO3g···O3f^iii	0.82	2.17	2.844 (3)	140
O2g—HO2g···OW	0.82	1.95	2.702 (3)	152
O4f—HO4f···O2g^iv	0.82	1.91	2.730 (3)	177
O3f—HO3f···O3g^iii	0.82	1.98	2.755 (3)	158
O2f—HO2f···O2f^iii	0.82	1.97	2.759 (2)	162

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1/2, y+1/2, −z; (iii) −x+1/2, y−1/2, −z+1; (iv) x−1/2, y−1/2, z.