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In methyl β-D-fructopyran­oside, C7H14O6, the thermodynamically most stable methyl glycoside of the ketose D-fructose, the pyran­ose ring is close to being an ideal 2C5 chair. The compound forms bilayers involving a complex hydrogen-bonding pattern of five independent hydrogen bonds. Graph-set analysis was applied to distinguish the hydrogen-bond patterns at unary and higher level graph sets.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110019888/jz3186sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110019888/jz3186Isup2.hkl
Contains datablock I

CCDC reference: 786805

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: PLATON (Spek, 2009).

Methyl β-D-fructopyranoside top
Crystal data top
C7H14O6F(000) = 416
Mr = 194.18Dx = 1.488 (1) Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 2304 reflections
a = 14.9990 (8) Åθ = 4.3–26.3°
b = 5.4114 (3) ŵ = 0.13 mm1
c = 10.8287 (6) ÅT = 200 K
β = 99.477 (5)°Platelet, colourless
V = 866.92 (8) Å30.51 × 0.49 × 0.15 mm
Z = 4
Data collection top
Oxford XCalibur CCD
diffractometer
914 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 26.3°, θmin = 4.3°
CCD; rotation images scansh = 1818
2704 measured reflectionsk = 66
976 independent reflectionsl = 913
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0603P)2 + 0.1474P]
where P = (Fo2 + 2Fc2)/3
976 reflections(Δ/σ)max < 0.001
123 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.21 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.22979 (10)0.7882 (3)0.79565 (17)0.0306 (4)
H810.26480.91000.79910.046*
O20.28321 (10)0.2751 (3)0.69063 (14)0.0245 (4)
O30.35951 (10)0.1116 (4)0.92245 (13)0.0260 (4)
H830.39200.07610.99090.039*
O40.53424 (10)0.0164 (3)0.85266 (14)0.0265 (4)
H840.53300.12950.82600.040*
O50.56719 (10)0.5123 (3)0.79179 (16)0.0284 (4)
H850.61820.44560.81040.043*
O60.37792 (9)0.6212 (3)0.71050 (12)0.0216 (3)
C10.27679 (15)0.5832 (5)0.8571 (2)0.0265 (5)
H110.23240.46790.88380.032*
H120.31670.64240.93330.032*
C20.33371 (13)0.4431 (4)0.77547 (18)0.0187 (5)
C30.40532 (13)0.2835 (4)0.85701 (18)0.0187 (4)
H30.44330.39270.91920.022*
C40.46606 (13)0.1586 (4)0.77620 (18)0.0198 (5)
H40.42880.04750.71420.024*
C50.50970 (14)0.3580 (4)0.7068 (2)0.0229 (5)
H50.54590.27810.64810.027*
C60.43646 (15)0.5152 (5)0.63279 (19)0.0250 (5)
H610.46470.64940.59060.030*
H620.40030.41250.56730.030*
C70.20559 (15)0.3736 (6)0.6120 (2)0.0344 (6)
H710.15690.39760.66110.052*
H720.18550.25820.54330.052*
H730.22100.53250.57770.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0189 (8)0.0189 (8)0.0548 (10)0.0011 (7)0.0085 (7)0.0009 (8)
O20.0192 (7)0.0231 (8)0.0288 (7)0.0011 (7)0.0026 (5)0.0054 (7)
O30.0228 (7)0.0299 (9)0.0245 (7)0.0060 (7)0.0017 (5)0.0077 (7)
O40.0269 (8)0.0187 (9)0.0310 (7)0.0065 (7)0.0041 (6)0.0026 (6)
O50.0155 (7)0.0217 (9)0.0474 (9)0.0013 (7)0.0036 (6)0.0026 (7)
O60.0199 (7)0.0184 (7)0.0279 (7)0.0014 (7)0.0082 (5)0.0015 (7)
C10.0224 (10)0.0252 (12)0.0330 (10)0.0028 (10)0.0078 (8)0.0020 (10)
C20.0166 (9)0.0168 (11)0.0224 (9)0.0020 (9)0.0019 (7)0.0006 (8)
C30.0160 (9)0.0171 (10)0.0231 (9)0.0013 (9)0.0035 (7)0.0005 (8)
C40.0174 (9)0.0177 (11)0.0235 (9)0.0030 (9)0.0005 (7)0.0021 (8)
C50.0205 (10)0.0208 (12)0.0293 (10)0.0015 (9)0.0095 (8)0.0020 (9)
C60.0247 (10)0.0252 (13)0.0265 (10)0.0038 (10)0.0087 (8)0.0045 (9)
C70.0219 (12)0.0422 (16)0.0351 (12)0.0026 (11)0.0067 (9)0.0046 (11)
Geometric parameters (Å, º) top
O1—C11.420 (3)C1—H120.9900
O1—H810.8400C2—C31.538 (3)
O2—C21.420 (2)C3—C41.522 (3)
O2—C71.427 (3)C3—H31.0000
O3—C31.414 (3)C4—C51.523 (3)
O3—H830.8400C4—H41.0000
O4—C41.430 (2)C5—C61.511 (3)
O4—H840.8400C5—H51.0000
O5—C51.424 (3)C6—H610.9900
O5—H850.8400C6—H620.9900
O6—C21.420 (3)C7—H710.9800
O6—C61.432 (3)C7—H720.9800
C1—C21.527 (3)C7—H730.9800
C1—H110.9900
C1—O1—H81109.5O4—C4—C3110.18 (15)
C2—O2—C7116.27 (18)O4—C4—C5110.03 (16)
C3—O3—H83109.5C3—C4—C5108.41 (18)
C4—O4—H84109.5O4—C4—H4109.4
C5—O5—H85109.5C3—C4—H4109.4
C2—O6—C6113.64 (17)C5—C4—H4109.4
O1—C1—C2113.48 (17)O5—C5—C6108.81 (18)
O1—C1—H11108.9O5—C5—C4111.10 (17)
C2—C1—H11108.9C6—C5—C4109.06 (17)
O1—C1—H12108.9O5—C5—H5109.3
C2—C1—H12108.9C6—C5—H5109.3
H11—C1—H12107.7C4—C5—H5109.3
O2—C2—O6110.91 (15)O6—C6—C5112.13 (16)
O2—C2—C1113.75 (16)O6—C6—H61109.2
O6—C2—C1107.53 (18)C5—C6—H61109.2
O2—C2—C3105.04 (17)O6—C6—H62109.2
O6—C2—C3109.06 (16)C5—C6—H62109.2
C1—C2—C3110.51 (16)H61—C6—H62107.9
O3—C3—C4112.47 (18)O2—C7—H71109.5
O3—C3—C2107.82 (16)O2—C7—H72109.5
C4—C3—C2110.29 (15)H71—C7—H72109.5
O3—C3—H3108.7O2—C7—H73109.5
C4—C3—H3108.7H71—C7—H73109.5
C2—C3—H3108.7H72—C7—H73109.5
C7—O2—C2—O668.6 (2)O6—C2—C3—C458.0 (2)
C7—O2—C2—C152.7 (2)C1—C2—C3—C4176.03 (18)
C7—O2—C2—C3173.69 (17)O3—C3—C4—O461.4 (2)
C6—O6—C2—O257.0 (2)C2—C3—C4—O4178.24 (16)
C6—O6—C2—C1178.08 (16)O3—C3—C4—C5178.19 (15)
C6—O6—C2—C358.22 (19)C2—C3—C4—C557.8 (2)
O1—C1—C2—O280.8 (2)O4—C4—C5—O556.7 (2)
O1—C1—C2—O642.4 (2)C3—C4—C5—O563.9 (2)
O1—C1—C2—C3161.32 (18)O4—C4—C5—C6176.63 (16)
O2—C2—C3—O362.26 (19)C3—C4—C5—C656.1 (2)
O6—C2—C3—O3178.81 (16)C2—O6—C6—C558.9 (2)
C1—C2—C3—O360.8 (2)O5—C5—C6—O664.9 (2)
O2—C2—C3—C460.9 (2)C4—C5—C6—O656.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H81···O2i0.842.343.029 (2)140
O1—H81···O3i0.842.092.802 (2)142
O3—H83···O4ii0.841.892.731 (2)177
O4—H84···O5iii0.842.052.868 (2)163
O5—H85···O1iv0.841.912.718 (2)162
C4—H4···O6iii1.002.433.226 (2)136
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z+2; (iii) x, y1, z; (iv) x+1/2, y1/2, z.
 

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