organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110019888/jz3186sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110019888/jz3186Isup2.hkl |
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).
Crystal data top
C7H14O6 | F(000) = 416 |
Mr = 194.18 | Dx = 1.488 (1) Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 2304 reflections |
a = 14.9990 (8) Å | θ = 4.3–26.3° |
b = 5.4114 (3) Å | µ = 0.13 mm−1 |
c = 10.8287 (6) Å | T = 200 K |
β = 99.477 (5)° | Platelet, colourless |
V = 866.92 (8) Å3 | 0.51 × 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 tube | Rint = 0.037 |
Graphite monochromator | θmax = 26.3°, θmin = 4.3° |
CCD; rotation images scans | h = −18→18 |
2704 measured reflections | k = −6→6 |
976 independent reflections | l = −9→13 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-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 parameters | Δρmax = 0.23 e Å−3 |
1 restraint | Δρmin = −0.21 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.22979 (10) | 0.7882 (3) | 0.79565 (17) | 0.0306 (4) | |
H81 | 0.2648 | 0.9100 | 0.7991 | 0.046* | |
O2 | 0.28321 (10) | 0.2751 (3) | 0.69063 (14) | 0.0245 (4) | |
O3 | 0.35951 (10) | 0.1116 (4) | 0.92245 (13) | 0.0260 (4) | |
H83 | 0.3920 | 0.0761 | 0.9909 | 0.039* | |
O4 | 0.53424 (10) | 0.0164 (3) | 0.85266 (14) | 0.0265 (4) | |
H84 | 0.5330 | −0.1295 | 0.8260 | 0.040* | |
O5 | 0.56719 (10) | 0.5123 (3) | 0.79179 (16) | 0.0284 (4) | |
H85 | 0.6182 | 0.4456 | 0.8104 | 0.043* | |
O6 | 0.37792 (9) | 0.6212 (3) | 0.71050 (12) | 0.0216 (3) | |
C1 | 0.27679 (15) | 0.5832 (5) | 0.8571 (2) | 0.0265 (5) | |
H11 | 0.2324 | 0.4679 | 0.8838 | 0.032* | |
H12 | 0.3167 | 0.6424 | 0.9333 | 0.032* | |
C2 | 0.33371 (13) | 0.4431 (4) | 0.77547 (18) | 0.0187 (5) | |
C3 | 0.40532 (13) | 0.2835 (4) | 0.85701 (18) | 0.0187 (4) | |
H3 | 0.4433 | 0.3927 | 0.9192 | 0.022* | |
C4 | 0.46606 (13) | 0.1586 (4) | 0.77620 (18) | 0.0198 (5) | |
H4 | 0.4288 | 0.0475 | 0.7142 | 0.024* | |
C5 | 0.50970 (14) | 0.3580 (4) | 0.7068 (2) | 0.0229 (5) | |
H5 | 0.5459 | 0.2781 | 0.6481 | 0.027* | |
C6 | 0.43646 (15) | 0.5152 (5) | 0.63279 (19) | 0.0250 (5) | |
H61 | 0.4647 | 0.6494 | 0.5906 | 0.030* | |
H62 | 0.4003 | 0.4125 | 0.5673 | 0.030* | |
C7 | 0.20559 (15) | 0.3736 (6) | 0.6120 (2) | 0.0344 (6) | |
H71 | 0.1569 | 0.3976 | 0.6611 | 0.052* | |
H72 | 0.1855 | 0.2582 | 0.5433 | 0.052* | |
H73 | 0.2210 | 0.5325 | 0.5777 | 0.052* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0189 (8) | 0.0189 (8) | 0.0548 (10) | 0.0011 (7) | 0.0085 (7) | −0.0009 (8) |
O2 | 0.0192 (7) | 0.0231 (8) | 0.0288 (7) | −0.0011 (7) | −0.0026 (5) | −0.0054 (7) |
O3 | 0.0228 (7) | 0.0299 (9) | 0.0245 (7) | −0.0060 (7) | 0.0017 (5) | 0.0077 (7) |
O4 | 0.0269 (8) | 0.0187 (9) | 0.0310 (7) | 0.0065 (7) | −0.0041 (6) | −0.0026 (6) |
O5 | 0.0155 (7) | 0.0217 (9) | 0.0474 (9) | 0.0013 (7) | 0.0036 (6) | −0.0026 (7) |
O6 | 0.0199 (7) | 0.0184 (7) | 0.0279 (7) | 0.0014 (7) | 0.0082 (5) | 0.0015 (7) |
C1 | 0.0224 (10) | 0.0252 (12) | 0.0330 (10) | 0.0028 (10) | 0.0078 (8) | −0.0020 (10) |
C2 | 0.0166 (9) | 0.0168 (11) | 0.0224 (9) | −0.0020 (9) | 0.0019 (7) | −0.0006 (8) |
C3 | 0.0160 (9) | 0.0171 (10) | 0.0231 (9) | −0.0013 (9) | 0.0035 (7) | −0.0005 (8) |
C4 | 0.0174 (9) | 0.0177 (11) | 0.0235 (9) | 0.0030 (9) | 0.0005 (7) | −0.0021 (8) |
C5 | 0.0205 (10) | 0.0208 (12) | 0.0293 (10) | 0.0015 (9) | 0.0095 (8) | −0.0020 (9) |
C6 | 0.0247 (10) | 0.0252 (13) | 0.0265 (10) | 0.0038 (10) | 0.0087 (8) | 0.0045 (9) |
C7 | 0.0219 (12) | 0.0422 (16) | 0.0351 (12) | 0.0026 (11) | −0.0067 (9) | −0.0046 (11) |
Geometric parameters (Å, º) top
O1—C1 | 1.420 (3) | C1—H12 | 0.9900 |
O1—H81 | 0.8400 | C2—C3 | 1.538 (3) |
O2—C2 | 1.420 (2) | C3—C4 | 1.522 (3) |
O2—C7 | 1.427 (3) | C3—H3 | 1.0000 |
O3—C3 | 1.414 (3) | C4—C5 | 1.523 (3) |
O3—H83 | 0.8400 | C4—H4 | 1.0000 |
O4—C4 | 1.430 (2) | C5—C6 | 1.511 (3) |
O4—H84 | 0.8400 | C5—H5 | 1.0000 |
O5—C5 | 1.424 (3) | C6—H61 | 0.9900 |
O5—H85 | 0.8400 | C6—H62 | 0.9900 |
O6—C2 | 1.420 (3) | C7—H71 | 0.9800 |
O6—C6 | 1.432 (3) | C7—H72 | 0.9800 |
C1—C2 | 1.527 (3) | C7—H73 | 0.9800 |
C1—H11 | 0.9900 | ||
C1—O1—H81 | 109.5 | O4—C4—C3 | 110.18 (15) |
C2—O2—C7 | 116.27 (18) | O4—C4—C5 | 110.03 (16) |
C3—O3—H83 | 109.5 | C3—C4—C5 | 108.41 (18) |
C4—O4—H84 | 109.5 | O4—C4—H4 | 109.4 |
C5—O5—H85 | 109.5 | C3—C4—H4 | 109.4 |
C2—O6—C6 | 113.64 (17) | C5—C4—H4 | 109.4 |
O1—C1—C2 | 113.48 (17) | O5—C5—C6 | 108.81 (18) |
O1—C1—H11 | 108.9 | O5—C5—C4 | 111.10 (17) |
C2—C1—H11 | 108.9 | C6—C5—C4 | 109.06 (17) |
O1—C1—H12 | 108.9 | O5—C5—H5 | 109.3 |
C2—C1—H12 | 108.9 | C6—C5—H5 | 109.3 |
H11—C1—H12 | 107.7 | C4—C5—H5 | 109.3 |
O2—C2—O6 | 110.91 (15) | O6—C6—C5 | 112.13 (16) |
O2—C2—C1 | 113.75 (16) | O6—C6—H61 | 109.2 |
O6—C2—C1 | 107.53 (18) | C5—C6—H61 | 109.2 |
O2—C2—C3 | 105.04 (17) | O6—C6—H62 | 109.2 |
O6—C2—C3 | 109.06 (16) | C5—C6—H62 | 109.2 |
C1—C2—C3 | 110.51 (16) | H61—C6—H62 | 107.9 |
O3—C3—C4 | 112.47 (18) | O2—C7—H71 | 109.5 |
O3—C3—C2 | 107.82 (16) | O2—C7—H72 | 109.5 |
C4—C3—C2 | 110.29 (15) | H71—C7—H72 | 109.5 |
O3—C3—H3 | 108.7 | O2—C7—H73 | 109.5 |
C4—C3—H3 | 108.7 | H71—C7—H73 | 109.5 |
C2—C3—H3 | 108.7 | H72—C7—H73 | 109.5 |
C7—O2—C2—O6 | −68.6 (2) | O6—C2—C3—C4 | −58.0 (2) |
C7—O2—C2—C1 | 52.7 (2) | C1—C2—C3—C4 | −176.03 (18) |
C7—O2—C2—C3 | 173.69 (17) | O3—C3—C4—O4 | −61.4 (2) |
C6—O6—C2—O2 | −57.0 (2) | C2—C3—C4—O4 | 178.24 (16) |
C6—O6—C2—C1 | 178.08 (16) | O3—C3—C4—C5 | 178.19 (15) |
C6—O6—C2—C3 | 58.22 (19) | C2—C3—C4—C5 | 57.8 (2) |
O1—C1—C2—O2 | −80.8 (2) | O4—C4—C5—O5 | −56.7 (2) |
O1—C1—C2—O6 | 42.4 (2) | C3—C4—C5—O5 | 63.9 (2) |
O1—C1—C2—C3 | 161.32 (18) | O4—C4—C5—C6 | −176.63 (16) |
O2—C2—C3—O3 | −62.26 (19) | C3—C4—C5—C6 | −56.1 (2) |
O6—C2—C3—O3 | 178.81 (16) | C2—O6—C6—C5 | −58.9 (2) |
C1—C2—C3—O3 | 60.8 (2) | O5—C5—C6—O6 | −64.9 (2) |
O2—C2—C3—C4 | 60.9 (2) | C4—C5—C6—O6 | 56.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H81···O2i | 0.84 | 2.34 | 3.029 (2) | 140 |
O1—H81···O3i | 0.84 | 2.09 | 2.802 (2) | 142 |
O3—H83···O4ii | 0.84 | 1.89 | 2.731 (2) | 177 |
O4—H84···O5iii | 0.84 | 2.05 | 2.868 (2) | 163 |
O5—H85···O1iv | 0.84 | 1.91 | 2.718 (2) | 162 |
C4—H4···O6iii | 1.00 | 2.43 | 3.226 (2) | 136 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y, −z+2; (iii) x, y−1, z; (iv) x+1/2, y−1/2, z. |