Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810001661X/an0575sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810001661X/an0575barafsup2.fcf | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810001661X/an0575lyx5sup3.fcf | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810001661X/an0575axylf8sup4.fcf |
CCDC references: 163051; 163052; 163053; 163054
Data collection: maXus (Nonius, 1998) for baraf_xray; 'custom software (Schultz, 1987)' for baraf_neutron; ILL programs Hklgen and Mad for axylf_neutron, alyxf_neutron. Cell refinement: maXus (Nonius, 1998) for baraf_xray; 'GSAS (Larson & Von Dreele, 1994)' for baraf_neutron; ILL program Rafd19 for axylf_neutron, alyxf_neutron. Data reduction: maXus (Nonius, 1998) for baraf_xray; 'GSAS (Larson & Von Dreele, 1994)' for baraf_neutron; 'ILL program Retreat (Wilkinson et al., 1988)' for axylf_neutron, alyxf_neutron. Program(s) used to solve structure: 'SHELXS97 (Sheldrick, 1990)' for baraf_xray, axylf_neutron, alyxf_neutron; 'from x-ray structure' for baraf_neutron. Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for baraf_xray, axylf_neutron, alyxf_neutron; 'GSAS (Larson & Von Dreele, 1994)' for baraf_neutron. For all compounds, molecular graphics: PLATON (A.L.Spek ,2000). Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) for baraf_xray, axylf_neutron, alyxf_neutron; manual for baraf_neutron.
C6H12O5 | Dx = 1.401 Mg m−3 |
Mr = 164.16 | Mo Kα radiation, λ = 0.71070 Å |
Orthorhombic, P212121 | Cell parameters from 600 reflections |
a = 5.906 (1) Å | θ = 8–25° |
b = 10.845 (3) Å | µ = 0.12 mm−1 |
c = 12.154 (3) Å | T = 100 K |
V = 778.5 (2) Å3 | Rectangular prism, clear blank white |
Z = 4 | 0.4 × 0.1 × 0.1 mm |
F(000) = 352 |
Nonius Kappa-CCD diffractometer | 2219 reflections with > 4σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 30.9°, θmin = 2.5° |
combination of psi and phi oscillations scans | h = 0→8 |
2313 measured reflections | k = 0→15 |
2313 independent reflections | l = −16→17 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0517P)2 + 0.0636P] where P = (Fo2 + 2Fc2)/3' |
S = 1.00 | (Δ/σ)max = 0.017 |
1365 reflections | Δρmax = 0.24 e Å−3 |
148 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.6 (6) |
C6H12O5 | V = 778.5 (2) Å3 |
Mr = 164.16 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.906 (1) Å | µ = 0.12 mm−1 |
b = 10.845 (3) Å | T = 100 K |
c = 12.154 (3) Å | 0.4 × 0.1 × 0.1 mm |
Nonius Kappa-CCD diffractometer | 2219 reflections with > 4σ(I) |
2313 measured reflections | Rint = 0.000 |
2313 independent reflections |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.076 | Δρmax = 0.24 e Å−3 |
S = 1.00 | Δρmin = −0.20 e Å−3 |
1365 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
148 parameters | Absolute structure parameter: 0.6 (6) |
0 restraints |
Experimental. The crystal was flash-frozen in Paratone-N oil. |
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 | 0.20919 (12) | 0.19581 (6) | 0.19598 (5) | 0.02242 (14) | |
O3 | 0.33979 (11) | 0.44942 (6) | 0.45934 (5) | 0.02032 (14) | |
H13 | 0.427 (3) | 0.4119 (14) | 0.5017 (16) | 0.045 (4)* | |
O4 | 0.10562 (11) | 0.40443 (6) | 0.19685 (5) | 0.02090 (14) | |
O2 | 0.12255 (12) | 0.18433 (6) | 0.41985 (5) | 0.02161 (14) | |
H12 | 0.242 (4) | 0.1437 (17) | 0.3963 (17) | 0.052 (5)* | |
O5 | 0.49691 (14) | 0.55965 (7) | 0.11385 (6) | 0.02812 (17) | |
H15 | 0.402 (3) | 0.5439 (13) | 0.0673 (13) | 0.033 (4)* | |
C4 | 0.28720 (14) | 0.45762 (8) | 0.26152 (7) | 0.01753 (15) | |
H4 | 0.239 (2) | 0.5406 (11) | 0.2836 (10) | 0.015 (3)* | |
C3 | 0.31500 (14) | 0.37593 (7) | 0.36319 (6) | 0.01674 (15) | |
H3 | 0.450 (2) | 0.3202 (11) | 0.3540 (10) | 0.017 (3)* | |
C2 | 0.10185 (15) | 0.29605 (8) | 0.36129 (7) | 0.01803 (15) | |
H2 | −0.017 (2) | 0.3430 (11) | 0.3926 (11) | 0.021 (3)* | |
C5 | 0.50361 (15) | 0.46571 (8) | 0.19544 (7) | 0.02094 (17) | |
H5A | 0.620 (2) | 0.4858 (12) | 0.2471 (12) | 0.024 (3)* | |
H5B | 0.532 (2) | 0.3814 (12) | 0.1625 (11) | 0.023 (3)* | |
C1 | 0.05974 (15) | 0.28475 (8) | 0.23740 (8) | 0.01961 (17) | |
H1 | −0.092 (2) | 0.2685 (12) | 0.2172 (11) | 0.023 (3)* | |
C6 | 0.1762 (2) | 0.17174 (10) | 0.08154 (8) | 0.0301 (2) | |
H6A | 0.303 (3) | 0.1109 (14) | 0.0595 (15) | 0.036 (4)* | |
H6B | 0.179 (3) | 0.2490 (15) | 0.0388 (13) | 0.038 (4)* | |
H6C | 0.024 (3) | 0.1348 (14) | 0.0673 (13) | 0.038 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0260 (3) | 0.0235 (3) | 0.0177 (3) | 0.0037 (3) | −0.0007 (2) | −0.0024 (2) |
O3 | 0.0245 (3) | 0.0216 (3) | 0.0148 (3) | 0.0024 (2) | −0.0025 (2) | 0.0001 (2) |
O4 | 0.0205 (3) | 0.0218 (3) | 0.0204 (3) | −0.0002 (2) | −0.0045 (2) | 0.0053 (2) |
O2 | 0.0242 (3) | 0.0188 (3) | 0.0217 (3) | 0.0021 (2) | 0.0076 (2) | 0.0052 (2) |
O5 | 0.0283 (3) | 0.0365 (4) | 0.0196 (3) | −0.0128 (3) | −0.0052 (3) | 0.0118 (3) |
C4 | 0.0200 (4) | 0.0165 (3) | 0.0160 (3) | 0.0008 (3) | −0.0011 (3) | 0.0010 (3) |
C3 | 0.0186 (4) | 0.0169 (3) | 0.0148 (3) | 0.0020 (3) | 0.0010 (3) | 0.0018 (3) |
C2 | 0.0187 (3) | 0.0167 (3) | 0.0187 (4) | 0.0020 (3) | 0.0032 (3) | 0.0023 (3) |
C5 | 0.0212 (4) | 0.0253 (4) | 0.0164 (4) | −0.0030 (3) | −0.0003 (3) | 0.0049 (3) |
C1 | 0.0186 (4) | 0.0197 (4) | 0.0204 (4) | −0.0001 (3) | −0.0009 (3) | 0.0019 (3) |
C6 | 0.0376 (5) | 0.0350 (5) | 0.0179 (4) | −0.0016 (4) | −0.0009 (4) | −0.0049 (4) |
O1—C1 | 1.4010 (11) | C4—H4 | 0.981 (12) |
O1—C6 | 1.4286 (12) | C3—C2 | 1.5283 (12) |
O3—C3 | 1.4221 (10) | C3—H3 | 1.005 (12) |
O3—H13 | 0.836 (19) | C2—C1 | 1.5310 (12) |
O4—C1 | 1.4145 (11) | C2—H2 | 0.949 (14) |
O4—C4 | 1.4494 (10) | C5—H5A | 0.955 (14) |
O2—C2 | 1.4105 (10) | C5—H5B | 1.012 (13) |
O2—H12 | 0.88 (2) | C1—H1 | 0.943 (14) |
O5—C5 | 1.4223 (10) | C6—H6A | 1.035 (16) |
O5—H15 | 0.816 (17) | C6—H6B | 0.987 (16) |
C4—C5 | 1.5121 (12) | C6—H6C | 0.999 (19) |
C4—C3 | 1.5292 (11) | ||
C1—O1—C6 | 112.93 (8) | C3—C2—H2 | 107.5 (8) |
C3—O3—H13 | 107.3 (12) | C1—C2—H2 | 108.5 (8) |
C1—O4—C4 | 108.54 (6) | O5—C5—C4 | 112.86 (7) |
C2—O2—H12 | 109.6 (13) | O5—C5—H5A | 108.4 (8) |
C5—O5—H15 | 110.6 (10) | C4—C5—H5A | 105.7 (9) |
O4—C4—C5 | 111.13 (7) | O5—C5—H5B | 112.1 (8) |
O4—C4—C3 | 106.68 (7) | C4—C5—H5B | 107.3 (8) |
C5—C4—C3 | 111.84 (7) | H5A—C5—H5B | 110.4 (11) |
O4—C4—H4 | 107.4 (7) | O1—C1—O4 | 112.69 (7) |
C5—C4—H4 | 109.7 (7) | O1—C1—C2 | 107.83 (7) |
C3—C4—H4 | 109.9 (7) | O4—C1—C2 | 103.78 (7) |
O3—C3—C2 | 114.51 (7) | O1—C1—H1 | 112.0 (8) |
O3—C3—C4 | 110.51 (6) | O4—C1—H1 | 105.2 (8) |
C2—C3—C4 | 103.16 (7) | C2—C1—H1 | 115.1 (8) |
O3—C3—H3 | 110.3 (7) | O1—C6—H6A | 105.6 (10) |
C2—C3—H3 | 108.0 (7) | O1—C6—H6B | 110.8 (9) |
C4—C3—H3 | 110.1 (7) | H6A—C6—H6B | 113.1 (13) |
O2—C2—C3 | 114.07 (7) | O1—C6—H6C | 111.4 (9) |
O2—C2—C1 | 116.20 (7) | H6A—C6—H6C | 110.6 (12) |
C3—C2—C1 | 101.19 (6) | H6B—C6—H6C | 105.4 (13) |
O2—C2—H2 | 108.8 (7) |
C6H12O5 | Z = 4 |
Mr = 164.16 | Dx = 1.409 Mg m−3 |
Orthorhombic, P212121 | Neutron radiation, λ = 0.7-4.2 Å |
a = 5.901 (1) Å | µ = wavelength-dependent mm−1 |
b = 10.791 (2) Å | T = 20 K |
c = 12.151 (2) Å | Rectangular prism, clear blank white |
V = 773.8 (2) Å3 | 2.0 × 2.0 × 1.0 mm |
'position-sensitive, 6-Li-glass area detector' diffractometer | 4688 independent reflections |
Radiation source: spallation source (IPNS) | 2977 reflections with > 3σ(I) |
time–of–flight histogram analysis (Jacobson, 1986) scans | θmax = 61.0°, θmin = 1.0° |
Absorption correction: for a sphere ? | h = 0→8 |
Tmin = ?, Tmax = ? | k = 0→15 |
4688 measured reflections | l = 0→17 |
Refinement on F2 | Primary atom site location: from X-ray |
Least-squares matrix: full | Secondary atom site location: from X-ray |
R[F2 > 2σ(F2)] = 0.100 | Hydrogen site location: structure-invariant direct methods |
wR(F2) = 0.117 | All H-atom parameters refined |
S = 1.10 | Weighting scheme based on measured s.u.'s SigmaFoSq = SigmaFoSq + (.002*FoSq)2 Wght = 1.0/(SigmaFoSq)2 All single crystal weights were scaled by Min(Fo/Fc,Fc/Fo)4 |
4688 reflections | (Δ/σ)max = 0.001 |
226 parameters | Extinction correction: Wavelength-dependent spherical absorption correction using cross-sections from Sears (1986), followed by a secondary extinction correction (Type-II) during final refinement. |
0 restraints | Extinction coefficient: 0.0002958 |
C6H12O5 | V = 773.8 (2) Å3 |
Mr = 164.16 | Z = 4 |
Orthorhombic, P212121 | Neutron radiation, λ = 0.7-4.2 Å |
a = 5.901 (1) Å | µ = wavelength-dependent mm−1 |
b = 10.791 (2) Å | T = 20 K |
c = 12.151 (2) Å | 2.0 × 2.0 × 1.0 mm |
'position-sensitive, 6-Li-glass area detector' diffractometer | 4688 measured reflections |
Absorption correction: for a sphere ? | 4688 independent reflections |
Tmin = ?, Tmax = ? | 2977 reflections with > 3σ(I) |
R[F2 > 2σ(F2)] = 0.100 | 226 parameters |
wR(F2) = 0.117 | 0 restraints |
S = 1.10 | All H-atom parameters refined |
4688 reflections |
Experimental. The atomic and magnetic scattering factors for 3 types of atoms were: Atom b-len a(1) b(1) a(2) b(2) a(3) b(3) a(4) b(4) c O. 581 3.04850 13.27710 2.28680 5.70110 1.54630. 32390. 86700 32.90890. 25080 C. 665 2.31000 20.84390 1.02000 10.20750 1.58860. 56870. 86500 51.65120. 21560 H -.374. 49300 10.51090. 32291 26.12570. 14019 3.14236. 04081 57.79970. 00304 |
Refinement. Symmetry-related reflections were not averaged since different extinction factors are applicable to reflections measured at different wavelengths. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2069 (3) | 0.19567 (14) | 0.19516 (14) | 0.0081 | |
O2 | 0.1172 (3) | 0.18482 (14) | 0.41910 (13) | 0.0063 | |
O3 | 0.3368 (3) | 0.45047 (16) | 0.45886 (13) | 0.0067 | |
O4 | 0.1037 (3) | 0.40547 (14) | 0.19599 (13) | 0.0067 | |
O5 | 0.4990 (3) | 0.56000 (16) | 0.11330 (13) | 0.0088 | |
C1 | 0.0565 (2) | 0.28563 (13) | 0.23639 (11) | 0.0059 | |
C2 | 0.0965 (2) | 0.29667 (12) | 0.36087 (11) | 0.0052 | |
C3 | 0.3121 (2) | 0.37679 (12) | 0.36319 (11) | 0.0047 | |
C4 | 0.2866 (3) | 0.45931 (12) | 0.26050 (11) | 0.0058 | |
C5 | 0.5044 (3) | 0.46645 (13) | 0.19501 (12) | 0.0068 | |
C6 | 0.1748 (3) | 0.17180 (14) | 0.08093 (12) | 0.0101 | |
H1 | −0.1200 (6) | 0.2630 (4) | 0.2123 (3) | 0.0186 | |
H2 | −0.0459 (6) | 0.3489 (3) | 0.3963 (3) | 0.0176 | |
H3 | 0.4581 (6) | 0.3142 (3) | 0.3539 (3) | 0.0180 | |
H4 | 0.2332 (6) | 0.5533 (3) | 0.2849 (3) | 0.0187 | |
H5A | 0.6459 (6) | 0.4885 (4) | 0.2503 (3) | 0.0215 | |
H5B | 0.5384 (8) | 0.3749 (4) | 0.1583 (3) | 0.0227 | |
H6A | 0.3039 (9) | 0.1070 (4) | 0.0563 (3) | 0.0281 | |
H6B | 0.1939 (10) | 0.2564 (4) | 0.0334 (3) | 0.0289 | |
H6C | 0.0105 (8) | 0.1319 (5) | 0.0656 (4) | 0.0301 | |
H12 | 0.2583 (7) | 0.1414 (3) | 0.4011 (3) | 0.0184 | |
H13 | 0.4393 (7) | 0.4052 (4) | 0.5093 (3) | 0.0197 | |
H15 | 0.3833 (7) | 0.5439 (4) | 0.0578 (3) | 0.0213 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0101 (6) | 0.0075 (5) | 0.0067 (5) | 0.0012 (5) | −0.0007 (6) | −0.0006 (4) |
O2 | 0.0075 (5) | 0.0058 (5) | 0.0055 (5) | −0.0001 (5) | 0.0002 (5) | 0.0019 (4) |
O3 | 0.0073 (5) | 0.0080 (5) | 0.0050 (5) | 0.0017 (5) | −0.0010 (5) | −0.0002 (4) |
O4 | 0.0072 (5) | 0.0072 (5) | 0.0057 (5) | 0.0003 (5) | 0.0001 (5) | 0.0017 (4) |
O5 | 0.0100 (6) | 0.0114 (6) | 0.0050 (5) | −0.0033 (6) | −0.0024 (6) | 0.0027 (4) |
C1 | 0.0067 (4) | 0.0064 (5) | 0.0045 (4) | −0.0004 (4) | −0.0005 (4) | 0.0014 (3) |
C2 | 0.0055 (4) | 0.0046 (4) | 0.0054 (4) | 0.0008 (4) | 0.0012 (4) | 0.0005 (3) |
C3 | 0.0053 (4) | 0.0053 (4) | 0.0036 (4) | −0.0010 (4) | 0.0010 (4) | 0.0002 (3) |
C4 | 0.0070 (5) | 0.0052 (4) | 0.0052 (4) | −0.0001 (4) | 0.0007 (4) | 0.0001 (3) |
C5 | 0.0077 (4) | 0.0091 (5) | 0.0037 (4) | −0.0003 (4) | −0.0004 (5) | 0.0015 (4) |
C6 | 0.0130 (6) | 0.0115 (5) | 0.0059 (5) | 0.0004 (5) | −0.0015 (5) | −0.0014 (4) |
H1 | 0.0137 (12) | 0.0220 (14) | 0.0201 (14) | −0.0023 (11) | −0.0051 (12) | 0.0007 (10) |
H2 | 0.0167 (12) | 0.0186 (13) | 0.0175 (12) | 0.0038 (11) | 0.0037 (12) | −0.0007 (10) |
H3 | 0.0169 (12) | 0.0187 (13) | 0.0185 (12) | 0.0033 (11) | −0.0015 (13) | −0.0039 (11) |
H4 | 0.0228 (15) | 0.0124 (11) | 0.0208 (14) | −0.0027 (12) | 0.0003 (13) | −0.0030 (9) |
H5A | 0.0186 (13) | 0.0274 (16) | 0.0185 (13) | −0.0042 (14) | −0.0041 (13) | 0.0047 (12) |
H5B | 0.0283 (18) | 0.0179 (14) | 0.0219 (15) | 0.0008 (14) | 0.0033 (15) | −0.0028 (11) |
H6A | 0.032 (2) | 0.0311 (18) | 0.0215 (15) | 0.0163 (18) | −0.0003 (17) | −0.0033 (13) |
H5B | 0.0283 (18) | 0.0179 (14) | 0.0219 (15) | 0.0008 (14) | 0.0033 (15) | −0.0028 (11) |
H6A | 0.032 (2) | 0.0311 (18) | 0.0215 (15) | 0.0163 (18) | −0.0003 (17) | −0.0033 (13) |
H6B | 0.042 (2) | 0.0244 (16) | 0.0200 (14) | −0.0064 (19) | 0.004 (2) | 0.0070 (13) |
H6C | 0.0215 (16) | 0.044 (3) | 0.0245 (18) | −0.0094 (19) | −0.0034 (16) | −0.0098 (17) |
H12 | 0.0203 (14) | 0.0157 (13) | 0.0191 (13) | 0.0064 (11) | 0.0027 (13) | 0.0034 (10) |
H13 | 0.0220 (15) | 0.0232 (15) | 0.0138 (11) | 0.0016 (14) | −0.0063 (12) | 0.0024 (11) |
H15 | 0.0200 (13) | 0.0258 (15) | 0.0181 (13) | −0.0027 (14) | −0.0059 (13) | 0.0033 (12) |
O1—C1 | 1.407 (2) | C2—H2 | 1.099 (4) |
O1—C6 | 1.424 (2) | C3—C4 | 1.5404 (19) |
O2—C2 | 1.404 (2) | C3—H3 | 1.100 (4) |
O2—H12 | 0.981 (4) | C4—C5 | 1.513 (2) |
O3—C3 | 1.416 (2) | C4—H4 | 1.103 (4) |
O3—H13 | 0.990 (4) | C5—H5A | 1.098 (4) |
O4—C1 | 1.411 (2) | C5—H5B | 1.102 (4) |
O4—C4 | 1.455 (2) | C6—H6A | 1.077 (5) |
O5—C5 | 1.416 (2) | C6—H6B | 1.086 (4) |
O5—H15 | 0.975 (4) | C6—H6C | 1.077 (5) |
C2—C1 | 1.5355 (19) | H1—C1 | 1.109 (4) |
C2—C3 | 1.5387 (19) | ||
C1—O1—C6 | 112.75 (10) | C3—C2—H2 | 110.25 (16) |
C3—O3—H13 | 107.38 (12) | C1—C2—H2 | 108.08 (18) |
C1—O4—C4 | 108.9 (3) | O5—C5—C4 | 112.70 (14) |
C2—O2—H12 | 112.1 (3) | O5—C5—H5A | 107.0 (2) |
C5—O5—H15 | 110.2 (3) | C4—C5—H5A | 109.6 (3) |
O4—C4—C5 | 111.53 (12) | O5—C5—H5B | 113.1 (3) |
O4—C4—C3 | 106.15 (12) | C4—C5—H5B | 108.5 (3) |
C3—C4—C5 | 111.85 (11) | H5A—C5—H5B | 108.8 (3) |
O4—C4—H4 | 107.5 (2) | O1—C1—O4 | 112.59 (13) |
C3—C4—H4 | 110.0 (2) | O1—C1—C2 | 107.90 (12) |
C5—C4—H4 | 109.7 (2) | O4—C1—C2 | 103.97 (12) |
O3—C3—C2 | 114.56 (13) | O1—C1—H1 | 110.3 (2) |
O3—C3—C4 | 110.52 (12) | O4—C1—H1 | 107.2 (2) |
C2—C3—C4 | 103.24 (11) | C2—C1—H1 | 114.9 (2) |
O3—C3—H3 | 111.27 (19) | O1—C6—H6A | 107.1 (3) |
C2—C3—H3 | 107.1 (2) | O1—C6—H6B | 110.6 (3) |
C4—C3—H3 | 110.1 (3) | O1—C6—H6C | 111.1 (3) |
O2—C2—C3 | 113.69 (13) | H6A—C6—H6B | 108.9 (4) |
O2—C2—C1 | 116.29 (12) | H6A—C6—H6C | 109.2 (4) |
C1—C2—C3 | 100.87 (11) | H6B—C6—H6C | 109.7 (4) |
O2—C2—H2 | 108.43 (17) |
C6H12O5 | F(000) = 48 |
Mr = 164.16 | Dx = 1.488 Mg m−3 |
Monoclinic, P21 | Neutron radiation, λ = 0.95284 Å |
a = 6.2238 (2) Å | Cell parameters from 1577 reflections |
b = 8.1389 (2) Å | θ = 3–50° |
c = 7.3637 (2) Å | µ = 2.56 mm−1 |
β = 101.1465 (17)° | T = 20 K |
V = 365.97 (2) Å3 | Rectangular block, clear blank white |
Z = 2 | 3.5 × 1.12 × 1.11 mm |
'4x64 deg. position-sensitive detector (Thomas et. al., 1983) diffractometer | 1949 reflections with > 4σ(I) |
Radiation source: neutron reactor at ILL | Rint = 0.043 |
Ge (117) monochromator | θmax = 50.1°, θmin = 3.8° |
'ω scans in equatorial geometry' | h = −3→9 |
Absorption correction: analytical ? | k = −5→13 |
Tmin = 0.699, Tmax = 0.783 | l = −11→11 |
2323 measured reflections | 3 standard reflections every 50 reflections |
2323 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.040 | All H-atom parameters refined |
wR(F2) = 0.102 | ' w = 1/[σ2(Fo2) + (0.0729P)2 + 0.7096P] where P = (Fo2 + 2Fc2)/3' |
S = 1.11 | (Δ/σ)max = 0.003 |
1619 reflections | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
209 parameters | Extinction coefficient: 0.040 (6) |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (10) |
C6H12O5 | V = 365.97 (2) Å3 |
Mr = 164.16 | Z = 2 |
Monoclinic, P21 | Neutron radiation, λ = 0.95284 Å |
a = 6.2238 (2) Å | µ = 2.56 mm−1 |
b = 8.1389 (2) Å | T = 20 K |
c = 7.3637 (2) Å | 3.5 × 1.12 × 1.11 mm |
β = 101.1465 (17)° |
'4x64 deg. position-sensitive detector (Thomas et. al., 1983) diffractometer | 1949 reflections with > 4σ(I) |
Absorption correction: analytical ? | Rint = 0.043 |
Tmin = 0.699, Tmax = 0.783 | 3 standard reflections every 50 reflections |
2323 measured reflections | intensity decay: none |
2323 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 1 restraint |
wR(F2) = 0.102 | All H-atom parameters refined |
S = 1.11 | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
1619 reflections | Absolute structure parameter: 0 (10) |
209 parameters |
Experimental. Atomic scattering factors were taken from Sears (1992). |
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 | ||
C1 | 0.0947 (2) | 0.36155 (15) | 0.69963 (15) | 0.0055 (2) | |
H1 | −0.0841 (5) | 0.3840 (4) | 0.6814 (4) | 0.0181 (5) | |
C2 | 0.19469 (19) | 0.40631 (15) | 0.53273 (16) | 0.0054 (2) | |
H2 | 0.1235 (5) | 0.5224 (4) | 0.4743 (4) | 0.0167 (5) | |
C3 | 0.43401 (19) | 0.43370 (15) | 0.62512 (16) | 0.0054 (2) | |
H3 | 0.5108 (5) | 0.3118 (4) | 0.6547 (4) | 0.0163 (5) | |
C4 | 0.41324 (19) | 0.51615 (15) | 0.80960 (16) | 0.0058 (2) | |
H4 | 0.5367 (5) | 0.4684 (4) | 0.9256 (4) | 0.0182 (5) | |
C5 | 0.4280 (2) | 0.70172 (15) | 0.81958 (16) | 0.0067 (2) | |
H5A | 0.5955 (5) | 0.7422 (4) | 0.8162 (5) | 0.0201 (5) | |
H5B | 0.3906 (6) | 0.7377 (4) | 0.9542 (4) | 0.0222 (6) | |
C6 | 0.0258 (2) | 0.13438 (17) | 0.87799 (18) | 0.0087 (2) | |
H6A | 0.0639 (7) | 0.2035 (6) | 1.0071 (5) | 0.0290 (7) | |
H6B | 0.0728 (8) | 0.0069 (5) | 0.9033 (7) | 0.0306 (8) | |
H6C | −0.1517 (6) | 0.1376 (7) | 0.8236 (6) | 0.0297 (8) | |
O1 | 0.1421 (2) | 0.19638 (18) | 0.74350 (18) | 0.0067 (2) | |
O2 | 0.1612 (2) | 0.28913 (19) | 0.38810 (19) | 0.0068 (2) | |
H12 | 0.2496 (5) | 0.1911 (4) | 0.4279 (4) | 0.0197 (5) | |
O5 | 0.2872 (2) | 0.78399 (19) | 0.6721 (2) | 0.0080 (2) | |
H15 | 0.1332 (5) | 0.7667 (5) | 0.6791 (5) | 0.0212 (6) | |
O3 | 0.5571 (2) | 0.52824 (19) | 0.51914 (19) | 0.0073 (2) | |
H13 | 0.6138 (5) | 0.4522 (4) | 0.4349 (4) | 0.0193 (5) | |
O4 | 0.1974 (2) | 0.46977 (17) | 0.83997 (19) | 0.0066 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0060 (4) | 0.0057 (4) | 0.0052 (4) | −0.0003 (3) | 0.0020 (3) | −0.0005 (3) |
H1 | 0.0100 (10) | 0.0220 (13) | 0.0221 (12) | 0.0016 (9) | 0.0025 (8) | 0.0002 (10) |
C2 | 0.0055 (4) | 0.0048 (4) | 0.0059 (4) | 0.0002 (3) | 0.0011 (3) | 0.0002 (3) |
H2 | 0.0204 (11) | 0.0117 (10) | 0.0181 (11) | 0.0051 (10) | 0.0040 (9) | 0.0031 (9) |
C3 | 0.0054 (4) | 0.0047 (4) | 0.0061 (4) | −0.0002 (4) | 0.0012 (3) | −0.0003 (3) |
H3 | 0.0185 (11) | 0.0112 (10) | 0.0191 (11) | 0.0029 (9) | 0.0035 (9) | 0.0014 (8) |
C4 | 0.0068 (4) | 0.0050 (4) | 0.0053 (4) | −0.0003 (4) | 0.0004 (3) | 0.0004 (3) |
H4 | 0.0188 (11) | 0.0168 (12) | 0.0174 (10) | 0.0032 (9) | −0.0008 (9) | 0.0021 (9) |
C5 | 0.0079 (5) | 0.0053 (4) | 0.0069 (4) | −0.0009 (4) | 0.0015 (3) | −0.0005 (3) |
H5A | 0.0136 (11) | 0.0198 (12) | 0.0266 (13) | −0.0048 (10) | 0.0035 (9) | 0.0041 (10) |
H5B | 0.0323 (15) | 0.0202 (13) | 0.0150 (11) | 0.0003 (12) | 0.0068 (11) | −0.0052 (10) |
C6 | 0.0107 (5) | 0.0078 (5) | 0.0081 (5) | −0.0013 (4) | 0.0027 (4) | 0.0017 (4) |
H6A | 0.0414 (19) | 0.0324 (18) | 0.0154 (11) | −0.0086 (16) | 0.0108 (12) | −0.0068 (12) |
H6B | 0.042 (2) | 0.0148 (13) | 0.0392 (19) | 0.0049 (14) | 0.0184 (16) | 0.0097 (13) |
H6C | 0.0160 (13) | 0.044 (2) | 0.0283 (15) | −0.0050 (13) | 0.0025 (11) | 0.0077 (15) |
O1 | 0.0086 (5) | 0.0052 (5) | 0.0065 (5) | 0.0001 (4) | 0.0021 (4) | −0.0004 (4) |
O2 | 0.0074 (5) | 0.0067 (5) | 0.0058 (5) | −0.0007 (4) | 0.0004 (4) | −0.0013 (4) |
H12 | 0.0243 (13) | 0.0117 (11) | 0.0215 (12) | 0.0047 (10) | 0.0002 (10) | −0.0020 (9) |
O5 | 0.0081 (5) | 0.0063 (5) | 0.0098 (5) | 0.0014 (4) | 0.0025 (4) | 0.0023 (4) |
H15 | 0.0138 (11) | 0.0249 (15) | 0.0246 (13) | 0.0006 (10) | 0.0026 (10) | 0.0043 (11) |
O3 | 0.0075 (5) | 0.0063 (5) | 0.0087 (5) | −0.0012 (4) | 0.0027 (4) | −0.0010 (4) |
H13 | 0.0231 (13) | 0.0172 (12) | 0.0195 (11) | 0.0005 (11) | 0.0091 (10) | −0.0053 (10) |
O4 | 0.0081 (5) | 0.0062 (5) | 0.0063 (5) | −0.0021 (4) | 0.0033 (4) | −0.0015 (4) |
C1—O1 | 1.4007 (19) | C4—H4 | 1.104 (3) |
C1—O4 | 1.4132 (18) | C5—O5 | 1.4240 (19) |
C1—C2 | 1.5252 (16) | C5—H5A | 1.098 (3) |
C1—H1 | 1.110 (3) | C5—H5B | 1.101 (3) |
C2—O2 | 1.4147 (18) | C6—O1 | 1.4271 (19) |
C2—C3 | 1.5295 (17) | C6—H6A | 1.091 (4) |
C2—H2 | 1.096 (3) | C6—H6B | 1.085 (4) |
C3—O3 | 1.4209 (19) | C6—H6C | 1.101 (4) |
C3—C4 | 1.5428 (17) | O2—H12 | 0.982 (3) |
C3—H3 | 1.105 (3) | O5—H15 | 0.980 (3) |
C4—O4 | 1.4535 (18) | O3—H13 | 0.989 (3) |
C4—C5 | 1.5140 (18) | ||
O1—C1—O4 | 112.59 (11) | O4—C4—H4 | 108.4 (2) |
O1—C1—C2 | 108.32 (11) | C5—C4—H4 | 106.69 (19) |
O4—C1—C2 | 104.06 (10) | C3—C4—H4 | 111.35 (19) |
O1—C1—H1 | 110.4 (2) | O5—C5—C4 | 114.16 (11) |
O4—C1—H1 | 106.7 (2) | O5—C5—H5A | 106.8 (2) |
C2—C1—H1 | 114.75 (19) | C4—C5—H5A | 110.3 (2) |
O2—C2—C1 | 114.95 (11) | O5—C5—H5B | 110.8 (2) |
O2—C2—C3 | 114.98 (11) | C4—C5—H5B | 106.7 (2) |
C1—C2—C3 | 100.98 (9) | H5A—C5—H5B | 107.9 (3) |
O2—C2—H2 | 107.22 (19) | O1—C6—H6A | 111.7 (2) |
C1—C2—H2 | 109.00 (19) | O1—C6—H6B | 107.5 (2) |
C3—C2—H2 | 109.5 (2) | H6A—C6—H6B | 109.7 (4) |
O3—C3—C2 | 114.62 (11) | O1—C6—H6C | 110.3 (2) |
O3—C3—C4 | 113.20 (11) | H6A—C6—H6C | 109.8 (4) |
C2—C3—C4 | 102.41 (9) | H6B—C6—H6C | 107.7 (4) |
O3—C3—H3 | 109.6 (2) | C1—O1—C6 | 112.75 (12) |
C2—C3—H3 | 107.70 (19) | C2—O2—H12 | 109.3 (2) |
C4—C3—H3 | 108.91 (18) | C5—O5—H15 | 110.9 (2) |
O4—C4—C5 | 107.51 (11) | C3—O3—H13 | 107.5 (2) |
O4—C4—C3 | 105.05 (10) | C1—O4—C4 | 110.51 (11) |
C5—C4—C3 | 117.51 (10) |
C6H9.783D2.217O5 | Dx = 1.506 Mg m−3 |
Mr = 166.2 | Neutron radiation, λ = 0.95284 Å |
Orthorhombic, P212121 | Cell parameters from 1949 reflections |
a = 10.332 (3) Å | θ = 3–50° |
b = 15.446 (2) Å | µ = 2.14 mm−1 |
c = 4.614 (1) Å | T = 20 K |
V = 736.3 (3) Å3 | Rectangular needle, clear blank white |
Z = 4 | 6.7 × 1.3 × 1.1 mm |
F(000) = 221 |
'4x64 deg. position-sensitive detector (Thomas et. al., 1983) diffractometer | 1949 reflections with > 4σ(I) |
Radiation source: neutron reactor at ILL | Rint = 0.040 |
Ge (117) monochromator | θmax = 52.1°, θmin = 3.2° |
'ω scans in equatorial geometry' | h = −4→17 |
Absorption correction: analytical ? | k = −5→25 |
Tmin = 0.665, Tmax = 0.829 | l = −2→7 |
2791 measured reflections | 3 standard reflections every 50 reflections |
2036 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0141P)2 + 4.2536P] where P = (Fo2 + 2Fc2)/3 |
S = 1.23 | (Δ/σ)max < 0.001 |
2036 reflections | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
215 parameters | Extinction coefficient: 0.0161 (11) |
3 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (10) |
C6H9.783D2.217O5 | V = 736.3 (3) Å3 |
Mr = 166.2 | Z = 4 |
Orthorhombic, P212121 | Neutron radiation, λ = 0.95284 Å |
a = 10.332 (3) Å | µ = 2.14 mm−1 |
b = 15.446 (2) Å | T = 20 K |
c = 4.614 (1) Å | 6.7 × 1.3 × 1.1 mm |
'4x64 deg. position-sensitive detector (Thomas et. al., 1983) diffractometer | 1949 reflections with > 4σ(I) |
Absorption correction: analytical ? | Rint = 0.040 |
Tmin = 0.665, Tmax = 0.829 | 3 standard reflections every 50 reflections |
2791 measured reflections | intensity decay: none |
2036 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 3 restraints |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.23 | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
2036 reflections | Absolute structure parameter: 0 (10) |
215 parameters |
Experimental. Atomic scattering factors were taken from Sears (1992). |
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 | Occ. (<1) | |
C1 | −0.71775 (10) | 0.15156 (7) | 0.2425 (3) | 0.00489 (16) | |
H1 | −0.7137 (3) | 0.11884 (18) | 0.0302 (7) | 0.0178 (4) | |
C2 | −0.58410 (10) | 0.17232 (7) | 0.3689 (3) | 0.00498 (17) | |
H2 | −0.5925 (3) | 0.1698 (2) | 0.6066 (6) | 0.0179 (5) | |
C3 | −0.56211 (10) | 0.26672 (7) | 0.2821 (3) | 0.00504 (17) | |
H3 | −0.4906 (3) | 0.29905 (19) | 0.4196 (7) | 0.0177 (5) | |
C4 | −0.69916 (11) | 0.30098 (7) | 0.3245 (2) | 0.00512 (17) | |
H4 | −0.7204 (3) | 0.30436 (19) | 0.5602 (6) | 0.0180 (5) | |
C5 | −0.72594 (11) | 0.38786 (7) | 0.1845 (3) | 0.00629 (18) | |
H5A | −0.7060 (3) | 0.3847 (2) | −0.0481 (7) | 0.0214 (5) | |
H5B | −0.6603 (3) | 0.43621 (18) | 0.2816 (9) | 0.0227 (6) | |
C6 | −0.89127 (11) | 0.05315 (7) | 0.3225 (3) | 0.0089 (2) | |
H6A | −0.9648 (3) | 0.0956 (2) | 0.2300 (11) | 0.0281 (7) | |
H6B | −0.8563 (4) | 0.0083 (2) | 0.1579 (10) | 0.0313 (8) | |
H6C | −0.9336 (4) | 0.0167 (2) | 0.5002 (10) | 0.0296 (7) | |
O1 | −0.78588 (13) | 0.10159 (8) | 0.4427 (3) | 0.0072 (2) | |
O2 | −0.48778 (12) | 0.11402 (8) | 0.2712 (3) | 0.00614 (19) | |
H12 | −0.4336 (2) | 0.09936 (16) | 0.4396 (6) | 0.0142 (7) | 0.259 (10) |
D2 | −0.4336 (2) | 0.09936 (16) | 0.4396 (6) | 0.0142 (7) | 0.741 (8) |
O3 | −0.53067 (13) | 0.27315 (9) | −0.0162 (3) | 0.0070 (2) | |
H13 | −0.4392 (2) | 0.26271 (17) | −0.0454 (6) | 0.0144 (7) | 0.265 (9) |
D3 | −0.4392 (2) | 0.26271 (17) | −0.0454 (6) | 0.0144 (7) | 0.735 (8) |
O4 | −0.77866 (12) | 0.23423 (8) | 0.1956 (3) | 0.00618 (19) | |
O5 | −0.85566 (12) | 0.41635 (8) | 0.2337 (3) | 0.0067 (2) | |
H15 | −0.9083 (2) | 0.40055 (17) | 0.0658 (6) | 0.0148 (7) | 0.259 (10) |
D5 | −0.9083 (2) | 0.40055 (17) | 0.0658 (6) | 0.0148 (7) | 0.741 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0043 (3) | 0.0045 (3) | 0.0058 (4) | −0.0009 (3) | −0.0004 (3) | 0.0003 (3) |
H1 | 0.0202 (10) | 0.0170 (10) | 0.0163 (10) | 0.0016 (9) | −0.0010 (10) | −0.0046 (9) |
C2 | 0.0045 (4) | 0.0048 (3) | 0.0057 (4) | 0.0002 (3) | −0.0001 (3) | 0.0000 (3) |
H2 | 0.0187 (10) | 0.0226 (11) | 0.0123 (10) | 0.0025 (9) | −0.0001 (9) | 0.0015 (9) |
C3 | 0.0040 (3) | 0.0049 (3) | 0.0062 (4) | 0.0001 (3) | −0.0003 (3) | −0.0002 (3) |
H3 | 0.0166 (10) | 0.0185 (10) | 0.0179 (11) | −0.0031 (9) | −0.0045 (9) | −0.0031 (9) |
C4 | 0.0049 (4) | 0.0045 (3) | 0.0060 (4) | 0.0005 (3) | 0.0008 (3) | −0.0003 (3) |
H4 | 0.0226 (11) | 0.0194 (10) | 0.0121 (9) | 0.0008 (9) | 0.0030 (9) | −0.0006 (9) |
C5 | 0.0056 (4) | 0.0054 (3) | 0.0079 (4) | 0.0006 (3) | 0.0007 (3) | 0.0004 (3) |
H5A | 0.0232 (12) | 0.0261 (12) | 0.0148 (10) | 0.0057 (11) | 0.0054 (10) | 0.0038 (10) |
H5B | 0.0165 (10) | 0.0153 (9) | 0.0362 (17) | −0.0032 (8) | −0.0055 (12) | −0.0021 (11) |
C6 | 0.0061 (4) | 0.0065 (4) | 0.0140 (5) | −0.0011 (3) | 0.0007 (4) | 0.0005 (4) |
H6A | 0.0185 (10) | 0.0198 (11) | 0.046 (2) | 0.0033 (9) | −0.0111 (14) | 0.0028 (14) |
H6B | 0.0258 (13) | 0.0282 (14) | 0.040 (2) | −0.0032 (12) | 0.0049 (15) | −0.0195 (16) |
H6C | 0.0281 (15) | 0.0282 (15) | 0.0324 (17) | −0.0146 (13) | 0.0028 (14) | 0.0088 (14) |
O1 | 0.0060 (4) | 0.0065 (4) | 0.0090 (5) | −0.0015 (4) | 0.0002 (4) | 0.0012 (4) |
O2 | 0.0059 (4) | 0.0061 (4) | 0.0064 (5) | 0.0020 (3) | −0.0003 (4) | 0.0002 (4) |
H12 | 0.0138 (10) | 0.0159 (11) | 0.0130 (10) | 0.0041 (7) | −0.0027 (7) | 0.0018 (8) |
D2 | 0.0138 (10) | 0.0159 (11) | 0.0130 (10) | 0.0041 (7) | −0.0027 (7) | 0.0018 (8) |
O3 | 0.0054 (4) | 0.0081 (4) | 0.0076 (5) | 0.0006 (4) | 0.0017 (4) | 0.0017 (4) |
H13 | 0.0082 (9) | 0.0177 (11) | 0.0174 (11) | 0.0008 (7) | 0.0027 (8) | −0.0016 (9) |
D3 | 0.0082 (9) | 0.0177 (11) | 0.0174 (11) | 0.0008 (7) | 0.0027 (8) | −0.0016 (9) |
O4 | 0.0036 (4) | 0.0047 (4) | 0.0102 (5) | −0.0004 (3) | −0.0011 (4) | 0.0013 (4) |
O5 | 0.0052 (4) | 0.0064 (4) | 0.0085 (5) | 0.0012 (3) | 0.0001 (4) | 0.0002 (4) |
H15 | 0.0121 (10) | 0.0177 (11) | 0.0145 (11) | 0.0010 (7) | −0.0029 (7) | −0.0013 (8) |
D5 | 0.0121 (10) | 0.0177 (11) | 0.0145 (11) | 0.0010 (7) | −0.0029 (7) | −0.0013 (8) |
C1—O1 | 1.3943 (17) | C2—H2 | 1.101 (3) |
C1—O4 | 1.4399 (16) | C3—H3 | 1.094 (3) |
C1—C2 | 1.5329 (16) | C4—H4 | 1.111 (3) |
C2—O2 | 1.4159 (17) | C5—H5A | 1.094 (4) |
C2—C3 | 1.5292 (16) | C5—H5B | 1.104 (3) |
C3—O3 | 1.4178 (19) | O5—D5 | 0.977 (3) |
C3—C4 | 1.5242 (16) | O2—D2 | 0.984 (3) |
C4—O4 | 1.4461 (17) | O3—D3 | 0.968 (3) |
C4—C5 | 1.5148 (16) | O5—H15 | 0.977 (3) |
C5—O5 | 1.4289 (18) | O2—H12 | 0.984 (3) |
C6—O1 | 1.4328 (18) | O3—H13 | 0.968 (3) |
C1—H1 | 1.103 (3) | ||
O1—C1—O4 | 111.70 (11) | O4—C1—H1 | 106.82 (19) |
O1—C1—C2 | 108.57 (10) | C2—C1—H1 | 113.55 (19) |
O4—C1—C2 | 105.39 (9) | O2—C2—H2 | 110.50 (19) |
O2—C2—C3 | 114.74 (10) | C1—C2—H2 | 107.50 (19) |
O2—C2—C1 | 112.27 (10) | C3—C2—H2 | 107.84 (19) |
C3—C2—C1 | 103.51 (9) | O3—C3—H3 | 112.1 (2) |
O3—C3—C4 | 108.24 (10) | C2—C3—H3 | 112.56 (19) |
O3—C3—C2 | 110.81 (10) | C4—C3—H3 | 113.22 (19) |
C4—C3—C2 | 99.17 (9) | O4—C4—H4 | 108.90 (18) |
O4—C4—C5 | 110.65 (10) | C3—C4—H4 | 109.00 (18) |
O4—C4—C3 | 103.14 (9) | C5—C4—H4 | 109.87 (18) |
C5—C4—C3 | 114.99 (9) | O5—C5—H5A | 110.3 (2) |
O5—C5—C4 | 112.11 (10) | O5—C5—H5B | 107.67 (19) |
C1—O1—C6 | 114.60 (12) | C4—C5—H5A | 110.15 (19) |
C1—O4—C4 | 108.80 (10) | C4—C5—H5B | 108.3 (2) |
C2—O2—D2 | 107.15 (19) | O1—C6—H6A | 111.5 (2) |
C2—O2—H12 | 107.15 (19) | O1—C6—H6B | 110.5 (2) |
C3—O3—D3 | 110.3 (2) | O1—C6—H6C | 106.5 (2) |
C3—O3—H13 | 110.3 (2) | H5A—C5—H5B | 108.2 (3) |
C5—O5—D5 | 108.61 (18) | H6A—C6—H6B | 109.9 (4) |
C5—O5—H15 | 108.61 (18) | H6A—C6—H6C | 109.1 (3) |
O1—C1—H1 | 110.72 (18) | H6B—C6—H6C | 109.3 (3) |
Experimental details
(baraf_xray) | (baraf_neutron) | (axylf_neutron) | (alyxf_neutron) | |
Crystal data | ||||
Chemical formula | C6H12O5 | C6H12O5 | C6H12O5 | C6H9.783D2.217O5 |
Mr | 164.16 | 164.16 | 164.16 | 166.2 |
Crystal system, space group | Orthorhombic, P212121 | Orthorhombic, P212121 | Monoclinic, P21 | Orthorhombic, P212121 |
Temperature (K) | 100 | 20 | 20 | 20 |
a, b, c (Å) | 5.906 (1), 10.845 (3), 12.154 (3) | 5.901 (1), 10.791 (2), 12.151 (2) | 6.2238 (2), 8.1389 (2), 7.3637 (2) | 10.332 (3), 15.446 (2), 4.614 (1) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 90, 101.1465 (17), 90 | 90, 90, 90 |
V (Å3) | 778.5 (2) | 773.8 (2) | 365.97 (2) | 736.3 (3) |
Z | 4 | 4 | 2 | 4 |
Radiation type | Mo Kα | Neutron, λ = 0.7-4.2 Å | Neutron, λ = 0.95284 Å | Neutron, λ = 0.95284 Å |
µ (mm−1) | 0.12 | wavelength-dependent | 2.56 | 2.14 |
Crystal size (mm) | 0.4 × 0.1 × 0.1 | 2.0 × 2.0 × 1.0 | 3.5 × 1.12 × 1.11 | 6.7 × 1.3 × 1.1 |
Data collection | ||||
Diffractometer | Nonius Kappa-CCD diffractometer | 'position-sensitive, 6-Li-glass area detector' diffractometer | '4x64 deg. position-sensitive detector (Thomas et. al., 1983) diffractometer | '4x64 deg. position-sensitive detector (Thomas et. al., 1983) diffractometer |
Absorption correction | – | For a sphere | Analytical | Analytical |
Tmin, Tmax | – | ?, ? | 0.699, 0.783 | 0.665, 0.829 |
No. of measured, independent and observed reflections | 2313, 2313, 2219 [ > 4σ(I)] | 4688, 4688, 2977 [ > 3σ(I)] | 2323, 2323, 1949 [ > 4σ(I)] | 2791, 2036, 1949 [ > 4σ(I)] |
Rint | 0.000 | ? | 0.043 | 0.040 |
(sin θ/λ)max (Å−1) | 0.723 | – | 0.805 | 0.828 |
Distance from specimen to detector (mm) | – | h = 0→8, k = 0→15, l = 0→17 | – | – |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.076, 1.00 | 0.100, 0.117, 1.10 | 0.040, 0.102, 1.11 | 0.042, 0.085, 1.23 |
No. of reflections | 1365 | 4688 | 1619 | 2036 |
No. of parameters | 148 | 226 | 209 | 215 |
No. of restraints | 0 | 0 | 1 | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | All H-atom parameters refined | All H-atom parameters refined | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.24, −0.20 | ?, ? | ?, ? | ?, ? |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | ? | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 0.6 (6) | ? | 0 (10) | 0 (10) |
Computer programs: maXus (Nonius, 1998), 'custom software (Schultz, 1987)', ILL programs Hklgen and Mad, 'GSAS (Larson & Von Dreele, 1994)', ILL program Rafd19, 'ILL program Retreat (Wilkinson et al., 1988)', 'SHELXS97 (Sheldrick, 1990)', 'from x-ray structure', SHELXL97 (Sheldrick, 1997), PLATON (A.L.Spek ,2000), manual.
submitted separately