Redetermination of methyl 3,4-O-isopropyl­idene-β-D-fucopyran­oside monohydrate

Fun, H.-K.; Jebas, S.R.; Rai, S.; Shetty, P.; Isloor, A.M.

doi:10.1107/S1600536809012689

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages o1002-o1003

doi:10.1107/S1600536809012689

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Redetermination of methyl 3,4-O-isopropylidene-β-D-fucopyranoside monohydrate

Hoong-Kun Fun,^a ^*‡ Samuel Robinson Jebas,^a § Sankappa Rai,^b Prakash Shetty ^c and Arun M Isloor ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSyngene International Ltd, Biocon Park, Plot Nos. 2 & 3, Bommasandra 4th Phase, Jigani Link Rd, Bangalore 560 100, India, ^cDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India, and ^dDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 30 March 2009; accepted 3 April 2009; online 8 April 2009)

In the title compound, C₁₀H₁₈O₅·H₂O, the fucopyranoside ring adopts a chair conformation. The crystal packing is stabilized by intermolecular O—H⋯O and C—H⋯O hydrogen bonds together with intramolecular O⋯O [2.2936 (8) Å] and intermolecular O⋯O [2.7140 (8)–2.829 (3) Å] short contacts. The molecules 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_r = 236.26
Orthorhombic, P 2₁ 2₁ 2₁
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 (SADABS; 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[F² > 2σ(F²)] = 0.026
wR(F²) = 0.073
S = 1.13
3449 reflections
161 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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⋯O3^iv	0.96	2.51	3.4306 (9)	162
Symmetry codes: (i) x, y+1, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) x, y-1, z; (iv) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

Buttin has demonstrated that D-fucose (6-deoxy-D-galactose) is an effective gratuitous inducer of the galactose operon in Escherichia coli (Musso et al., 1963). 6-Deoxyhexose and its derivatives are important components of lipopolysaccharides in, amongst others, Vibrio cholerae O1 (Bilge et al., 1996), Brucella spc., Citrobacter freundii F90 (Villeneuve et al., 2000), Salmonella enterica O30, and Escherichia coli O157 (Wu & Mackenzie, 1987). Further investigation revealed that D-fucose derivatives are important component of a repeating pentasaccharide unit in O-chains of the LPS of Yersinia enterocolitica (Caroff, Bundle & Perry, 1984) and Brucella abortus (Caroff, Bundle, Perry, Cherwonogrodzky & Dunch, 1984). These findings established a molecular basis for extensive serological cross-reactivity between the various antigenic LPSs. These observations prompted us to synthesize the title compound, (I). Herein we report the synthesis and the redetermination of the crystal structure of the title compound.

The title compund has been determined previously (Spiers. 1931), but no R-values were given. The asymmetric unit of (I) (Fig.1) comprises of one molecule of methyl 3,4-O-isopropylidene -β-D–fucopyranoside and a water molecule. The isopropylidene-fucopyranoside ring is non-planar with the maximum deviation from planarity of 0.6532 (6) Å for the atom C5. The fucopyranoside ring adopts the chair conformation with the puckering parameters Q = 0.5344 (6), θ = 20.15 (7)° and ϕ = 22.3 (2)° (Cremer & Pople, 1975). The bond lengths (Allen et al., 1987) and bond angles show normal values.

The crystal packing is stabilized by O—H···O and C—H···O hydrogen bonds to form infinite one dimensional chain along the [100] direction (Fig. 2). Short contacts of O···O = 2.2936 (8) Å; O···Oⁱ = 2.7140 (8) Å; O···Oⁱⁱ = 2.7535 (8) Å & O···Oⁱⁱⁱ = 2.8293 (8) Å [symmetry codes: (i) x,1 + y,z; (ii) -1/2 + x,3/2 - y,-z & (iii) x,1 + y,z] are observed.

Related literature top

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 stability of the temperature controller, see: Cosier & Glazer (1986).

Experimental top

The title compound was obtained by stirring a solution of 1,2,3,4 di-O-isopropylidene -α-D-fucopyranoside (0.5 g, 2.1 mmol) in dry methanol (5 ml). To this was added 3M solution of HCl in methanol (5 ml) at 0°C under nitrogen atmosphere. Further the reaction mixture was stirred at ambient temperature for 12 h. The reaction mixture was neutralized with solid sodium bicarbonate (1 g), concentrated, and residue was purified by flash column chromatography using 5% methanol in chloroform as eluent to get compound as foam-like solid which was taken in dry dimethylformamide (5 ml) and to this was added PTSA (Para Toluene Sulphonic Acid) (0.015 g, 2.0 mmol) and 2,2-dimethoxypropane (1.13 g,10 mmol). The mixture was further stirred at ambient temperature for 12 more hours. TLC (30% EtOAc/hexane,Rf-0.5) shows complete conversion of the starting materials. Reaction mixture was neutralized with triethylamine (2 ml) and concentrated under vacuum, residue was purified by column chromatography using 25% ethylacetate in pet ether to get a colourless liquid and the title compound as a white solid, which was recrystalized using hot acetone (yield 0.40 g, 85%; m.p. 328–330 K).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the c axis, showing an extended molecular chain along the a axis. Dashed lines indicate the hydrogen bondings.

(I) top

Crystal data top

C₁₀H₁₈O₅·H₂O	F(000) = 512
M_r = 236.26	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0439P)² + 0.0731P] where P = (F_o² + 2F_c²)/3
3449 reflections	(Δ/σ)_max = 0.001
161 parameters	Δρ_max = 0.31 e Å⁻³
4 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₀H₁₈O₅·H₂O	V = 1168.90 (2) Å³
M_r = 236.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.5824 (1) Å	µ = 0.11 mm⁻¹
b = 9.2834 (1) Å	T = 100 K
c = 14.6711 (2) Å	0.50 × 0.27 × 0.27 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3449 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3337 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.971	R_int = 0.032
64045 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	4 restraints
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.31 e Å⁻³
3449 reflections	Δρ_min = −0.27 e Å⁻³
161 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.96	2.51	3.4306 (9)	162

Symmetry codes: (i) x, y+1, z; (ii) x+1/2, −y+3/2, −z; (iii) x, y−1, z; (iv) −x+1/2, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₈O₅·H₂O
M_r	236.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	8.5824 (1), 9.2834 (1), 14.6711 (2)
V (Å³)	1168.90 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.50 × 0.27 × 0.27

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.947, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	64045, 3449, 3337
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.857

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.073, 1.13
No. of reflections	3449
No. of parameters	161
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.27

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.96	2.51	3.4306 (9)	161.7

Symmetry codes: (i) x, y+1, z; (ii) x+1/2, −y+3/2, −z; (iii) x, y−1, z; (iv) −x+1/2, −y+2, z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5473-2009. Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post–doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. AMI is grateful to the Head of the Department of Chemistry and the Director, NITK, Surathkal, India, for providing research facilities. SR thanks Dr Gautam Das, Syngene International Ltd, Bangalore, India, for allocation of research resources.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
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Volume 65| Part 5| May 2009| Pages o1002-o1003

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Redetermination of methyl 3,4-O-iso­propyl­­idene-β-D-fuco­pyran­oside monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Redetermination of methyl 3,4-O-isopropylidene-β-D-fucopyranoside monohydrate