Redetermination of methyl 3,4-O-isopropyl-idene-β-D-fucopyran-oside monohydrate.

In the title compound, C(10)H(18)O(5)·H(2)O, the fucopyran-oside ring adopts a chair conformation. The crystal packing is stabilized by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds together with intra-molecular O⋯O [2.2936 (8) Å] and inter-molecular O⋯O [2.7140 (8)-2.829 (3) Å] short contacts. The mol-ecules are linked together to form an infinite chain along the a axis. This structure has been solved previously but with no R-values [Spiers (1931). Z. Kristallogr. Kristallgeom. Kristallphys. Kristallchem.78, 101].

Related literature

D-fucose (6-de­oxy-D-galactose) is an effective gratuitous inducer of the galactose operon in Escherichia coli, see: Musso et al. (1963 ▶). 6-Deoxy­hexose and its derivatives are important components of lipopolysaccharides, see: Bilge et al. (1996 ▶); Villeneuve et al. (2000 ▶); Wu & Mackenzie (1987 ▶); Caroff, Bundle & Perry (1984 ▶); Caroff, Bundle, Perry, Cherwonogrodzky & Dunch (1984 ▶). For a previous structure determination of the title compound, see: Spiers (1931 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H18O5·H2O

M = 236.26

Orthorhombic,

a = 8.5824 (1) Å

b = 9.2834 (1) Å

c = 14.6711 (2) Å

V = 1168.90 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.50 × 0.27 × 0.27 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.947, T max = 0.971

64045 measured reflections

3449 independent reflections

3337 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.073

S = 1.13

3449 reflections

161 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012689/is2405sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012689/is2405Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H18O5·H2O	F(000) = 512
Mr = 236.26	Dx = 1.343 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9413 reflections
a = 8.5824 (1) Å	θ = 2.8–41.6°
b = 9.2834 (1) Å	µ = 0.11 mm−1
c = 14.6711 (2) Å	T = 100 K
V = 1168.90 (2) Å3	Block, colourless
Z = 4	0.50 × 0.27 × 0.27 mm

Bruker SMART APEXII CCD area-detector diffractometer	3449 independent reflections
Radiation source: fine-focus sealed tube	3337 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 37.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
Tmin = 0.947, Tmax = 0.971	k = −15→15
64045 measured reflections	l = −25→25

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0439P)2 + 0.0731P] where P = (Fo2 + 2Fc2)/3
3449 reflections	(Δ/σ)max = 0.001
161 parameters	Δρmax = 0.31 e Å−3
4 restraints	Δρmin = −0.27 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat [Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107] operating at 100.0 (1) K.

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	0.43844 (6)	0.76639 (5)	0.05482 (3)	0.01206 (8)
O2	0.46299 (6)	0.72835 (6)	−0.14722 (3)	0.01333 (9)
O3	0.37807 (7)	0.95475 (6)	−0.18528 (3)	0.01399 (9)
O4	0.34767 (7)	1.13634 (6)	−0.01512 (4)	0.01634 (10)
O5	0.48979 (6)	0.97492 (6)	0.13084 (3)	0.01364 (9)
C1	0.38958 (8)	0.91139 (7)	0.06752 (4)	0.01172 (10)
H1A	0.2818	0.9145	0.0895	0.014*
C2	0.33053 (8)	0.68941 (7)	−0.00168 (4)	0.01206 (10)
H2A	0.2268	0.6964	0.0259	0.014*
C3	0.32312 (8)	0.75401 (7)	−0.09665 (4)	0.01172 (10)
H3A	0.2342	0.7132	−0.1296	0.014*
C4	0.46232 (8)	0.83123 (7)	−0.21980 (4)	0.01328 (10)
C5	0.31314 (7)	0.91860 (7)	−0.09849 (4)	0.01160 (10)
H5A	0.2038	0.9487	−0.0961	0.014*
C6	0.40456 (8)	0.99275 (7)	−0.02236 (4)	0.01164 (10)
H6A	0.5148	0.9961	−0.0396	0.014*
C7	0.37798 (10)	0.77431 (9)	−0.30350 (5)	0.01941 (13)
H7A	0.2738	0.7469	−0.2871	0.029*
H7B	0.4326	0.6920	−0.3269	0.029*
H7C	0.3742	0.8481	−0.3493	0.029*
C8	0.62911 (9)	0.87289 (9)	−0.24007 (5)	0.01995 (13)
H8A	0.6795	0.9026	−0.1848	0.030*
H8B	0.6305	0.9508	−0.2831	0.030*
H8C	0.6833	0.7917	−0.2653	0.030*
C9	0.46504 (9)	0.92419 (8)	0.22239 (4)	0.01716 (12)
H9A	0.5330	0.9749	0.2633	0.026*
H9B	0.4870	0.8229	0.2253	0.026*
H9C	0.3587	0.9409	0.2396	0.026*
C10	0.37923 (9)	0.53235 (7)	−0.00202 (5)	0.01627 (11)
H10A	0.3747	0.4950	0.0589	0.024*
H10B	0.4838	0.5243	−0.0247	0.024*
H10C	0.3101	0.4784	−0.0405	0.024*
O1W	0.57299 (7)	0.26179 (6)	0.08757 (4)	0.01852 (10)
H1O4	0.4072 (16)	1.1865 (15)	0.0151 (9)	0.032 (4)*
H1W1	0.6579 (13)	0.2881 (14)	0.0656 (9)	0.030 (4)*
H2W1	0.5836 (19)	0.1840 (12)	0.1158 (10)	0.041 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.01237 (19)	0.01127 (17)	0.01255 (18)	0.00025 (15)	−0.00175 (15)	0.00011 (15)
O2	0.01453 (19)	0.01320 (18)	0.01227 (18)	0.00295 (16)	0.00272 (15)	0.00221 (15)
O3	0.0180 (2)	0.01283 (19)	0.01116 (18)	0.00330 (17)	0.00186 (16)	0.00176 (15)
O4	0.0190 (2)	0.01123 (18)	0.0188 (2)	0.00316 (17)	−0.00409 (18)	−0.00123 (17)
O5	0.0155 (2)	0.0152 (2)	0.01031 (18)	−0.00255 (16)	−0.00114 (15)	−0.00001 (15)
C1	0.0116 (2)	0.0122 (2)	0.0114 (2)	0.00024 (19)	−0.00052 (18)	−0.00035 (18)
C2	0.0118 (2)	0.0122 (2)	0.0122 (2)	−0.00124 (18)	−0.00016 (19)	0.00084 (18)
C3	0.0112 (2)	0.0126 (2)	0.0114 (2)	−0.00007 (18)	−0.00006 (18)	0.00028 (19)
C4	0.0146 (2)	0.0138 (2)	0.0114 (2)	0.0020 (2)	0.00107 (19)	0.00140 (19)
C5	0.0111 (2)	0.0127 (2)	0.0110 (2)	0.00160 (18)	−0.00033 (18)	0.00072 (18)
C6	0.0119 (2)	0.0111 (2)	0.0119 (2)	0.00140 (17)	−0.00036 (18)	0.00060 (18)
C7	0.0262 (3)	0.0196 (3)	0.0124 (2)	0.0016 (3)	−0.0019 (2)	−0.0015 (2)
C8	0.0159 (3)	0.0246 (3)	0.0193 (3)	0.0013 (2)	0.0040 (2)	0.0059 (3)
C9	0.0185 (3)	0.0222 (3)	0.0107 (2)	−0.0003 (2)	0.0004 (2)	0.0003 (2)
C10	0.0199 (3)	0.0121 (2)	0.0169 (3)	−0.0007 (2)	−0.0002 (2)	0.0010 (2)
O1W	0.0186 (2)	0.0147 (2)	0.0223 (2)	−0.00180 (18)	−0.00014 (19)	0.00053 (19)

O1—C1	1.4222 (8)	C4—C7	1.5202 (10)
O1—C2	1.4336 (8)	C5—C6	1.5287 (9)
O2—C4	1.4304 (8)	C5—H5A	0.9800
O2—C3	1.4311 (8)	C6—H6A	0.9800
O3—C5	1.4299 (8)	C7—H7A	0.9600
O3—C4	1.4472 (8)	C7—H7B	0.9600
O4—C6	1.4236 (8)	C7—H7C	0.9600
O4—H1O4	0.821 (9)	C8—H8A	0.9600
O5—C1	1.3966 (8)	C8—H8B	0.9600
O5—C9	1.4389 (8)	C8—H8C	0.9600
C1—C6	1.5251 (9)	C9—H9A	0.9600
C1—H1A	0.9800	C9—H9B	0.9600
C2—C10	1.5168 (10)	C9—H9C	0.9600
C2—C3	1.5183 (9)	C10—H10A	0.9600
C2—H2A	0.9800	C10—H10B	0.9600
C3—C5	1.5306 (9)	C10—H10C	0.9600
C3—H3A	0.9800	O1W—H1W1	0.834 (8)
C4—C8	1.5123 (10)	O1W—H2W1	0.838 (8)
C1—O1—C2	110.92 (5)	C6—C5—H5A	109.7
C4—O2—C3	105.75 (5)	C3—C5—H5A	109.7
C5—O3—C4	108.68 (5)	O4—C6—C1	111.74 (5)
C6—O4—H1O4	111.0 (12)	O4—C6—C5	107.46 (5)
C1—O5—C9	113.06 (5)	C1—C6—C5	111.43 (5)
O5—C1—O1	107.78 (5)	O4—C6—H6A	108.7
O5—C1—C6	108.30 (5)	C1—C6—H6A	108.7
O1—C1—C6	109.30 (5)	C5—C6—H6A	108.7
O5—C1—H1A	110.5	C4—C7—H7A	109.5
O1—C1—H1A	110.5	C4—C7—H7B	109.5
C6—C1—H1A	110.5	H7A—C7—H7B	109.5
O1—C2—C10	107.64 (5)	C4—C7—H7C	109.5
O1—C2—C3	111.14 (5)	H7A—C7—H7C	109.5
C10—C2—C3	112.84 (6)	H7B—C7—H7C	109.5
O1—C2—H2A	108.4	C4—C8—H8A	109.5
C10—C2—H2A	108.4	C4—C8—H8B	109.5
C3—C2—H2A	108.4	H8A—C8—H8B	109.5
O2—C3—C2	112.02 (5)	C4—C8—H8C	109.5
O2—C3—C5	101.77 (5)	H8A—C8—H8C	109.5
C2—C3—C5	114.38 (5)	H8B—C8—H8C	109.5
O2—C3—H3A	109.5	O5—C9—H9A	109.5
C2—C3—H3A	109.5	O5—C9—H9B	109.5
C5—C3—H3A	109.5	H9A—C9—H9B	109.5
O2—C4—O3	105.70 (5)	O5—C9—H9C	109.5
O2—C4—C8	108.26 (6)	H9A—C9—H9C	109.5
O3—C4—C8	109.83 (6)	H9B—C9—H9C	109.5
O2—C4—C7	111.79 (6)	C2—C10—H10A	109.5
O3—C4—C7	108.67 (6)	C2—C10—H10B	109.5
C8—C4—C7	112.38 (6)	H10A—C10—H10B	109.5
O3—C5—C6	110.18 (5)	C2—C10—H10C	109.5
O3—C5—C3	103.19 (5)	H10A—C10—H10C	109.5
C6—C5—C3	114.08 (5)	H10B—C10—H10C	109.5
O3—C5—H5A	109.7	H1W1—O1W—H2W1	110.4 (12)
C9—O5—C1—O1	−72.50 (7)	C5—O3—C4—C8	−123.77 (6)
C9—O5—C1—C6	169.36 (6)	C5—O3—C4—C7	112.93 (6)
C2—O1—C1—O5	173.54 (5)	C4—O3—C5—C6	106.03 (6)
C2—O1—C1—C6	−68.96 (6)	C4—O3—C5—C3	−16.15 (7)
C1—O1—C2—C10	−172.91 (5)	O2—C3—C5—O3	33.37 (6)
C1—O1—C2—C3	63.06 (7)	C2—C3—C5—O3	154.36 (5)
C4—O2—C3—C2	−161.33 (5)	O2—C3—C5—C6	−86.15 (6)
C4—O2—C3—C5	−38.71 (6)	C2—C3—C5—C6	34.84 (8)
O1—C2—C3—O2	70.09 (7)	O5—C1—C6—O4	−66.61 (7)
C10—C2—C3—O2	−50.94 (7)	O1—C1—C6—O4	176.22 (5)
O1—C2—C3—C5	−45.05 (8)	O5—C1—C6—C5	173.15 (5)
C10—C2—C3—C5	−166.08 (6)	O1—C1—C6—C5	55.99 (7)
C3—O2—C4—O3	29.57 (7)	O3—C5—C6—O4	82.09 (6)
C3—O2—C4—C8	147.20 (6)	C3—C5—C6—O4	−162.42 (5)
C3—O2—C4—C7	−88.49 (7)	O3—C5—C6—C1	−155.19 (5)
C5—O3—C4—O2	−7.19 (7)	C3—C5—C6—C1	−39.69 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O1Wi	0.82 (1)	1.91 (1)	2.7140 (8)	166 (2)
O1W—H1W1···O4ii	0.83 (1)	1.92 (1)	2.7534 (8)	176 (1)
O1W—H2W1···O5iii	0.84 (1)	2.11 (1)	2.8294 (8)	143 (2)
C9—H9C···O3iv	0.96	2.51	3.4306 (9)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O1Wi	0.821 (9)	1.909 (9)	2.7140 (8)	166.4 (16)
O1W—H1W1⋯O4ii	0.834 (8)	1.921 (8)	2.7534 (8)	175.6 (14)
O1W—H2W1⋯O5iii	0.838 (8)	2.113 (11)	2.8294 (8)	143.3 (15)
C9—H9C⋯O3iv	0.96	2.51	3.4306 (9)	162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .