Easy crystallization distinguishes xylitol from other sugars, which usually condense into a syrup from aqueous solution. Although two polymorphs, i.e. metastable monoclinic and high-density orthorhombic, have been reported for xylitol, only the latter is in practical use. Under high pressure, the same orthorhombic phase has been obtained by both isothermal and isochoric recrystallization. The stability of the orthorhombic xylitol phase to 5.0 GPa has been correlated with a uniform compression of all hydrogen bonds and some flexibility of the molecular conformation, which cushion the pressure-induced local strains. The anisotropic compressibility of xylitol and its thermal expansion are consistent with the rule of inverse effects of pressure and temperature. This inverse strain relationship has been correlated with the dimensions and orientation of xylitol molecules in the crystal structure.
Supporting information
| Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520621000445/um5047sup1.cif Contains datablocks Xylitol0_0001GPa, Xylitol0_33GPa, Xylitol0_63GPa, Xylitol0_8GPa, Xylitol0_96GPa, Xylitol1_60GPa, Xylitol2GPa, Xylitol2_60GPa, Xylitol3_20GPa, Xylitol3_90GPa, Xylitol4_70GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol0_0001GPasup2.hkl Contains datablock Xylitol0_0001GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol0_33GPasup3.hkl Contains datablock Xylitol0_33GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol0_63GPasup4.hkl Contains datablock Xylitol0_63GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol0_8GPasup5.hkl Contains datablock Xylitol0_8GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol0_96GPasup6.hkl Contains datablock Xylitol0_96GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol1_60GPasup7.hkl Contains datablock Xylitol1_60GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol2GPasup8.hkl Contains datablock Xylitol2GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol2_60GPasup9.hkl Contains datablock Xylitol2_60GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol3_20GPasup10.hkl Contains datablock Xylitol3_20GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol3_90GPasup11.hkl Contains datablock Xylitol3_90GPa |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol4_70GPasup12.hkl Contains datablock Xylitol4_70GPa |
| Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520621000445/um5047Xylitol4_70GPasup13.cml Supplementary material |
| Portable Document Format (PDF) file https://doi.org/10.1107/S2052520621000445/um5047sup14.pdf Additional figures and tables |
CCDC references: 2021790; 2021791; 2021792; 2021793; 2021794; 2021795; 2021796; 2021797; 2021798; 2021799; 2021800
Data collection: CrysAlis PRO 1.171.38.46 (Rigaku OD, 2015) for Xylitol0_0001GPa. Cell refinement: CrysAlis PRO 1.171.38.46 (Rigaku OD, 2015) for Xylitol0_0001GPa. Data reduction: CrysAlis PRO 1.171.38.46 (Rigaku OD, 2015) for Xylitol0_0001GPa. Program(s) used to solve structure: ShelXT (Sheldrick, 2015) for Xylitol0_0001GPa, Xylitol0_33GPa; SHELXS (Sheldrick, 2008) for Xylitol0_8GPa, Xylitol0_96GPa, Xylitol1_60GPa, Xylitol2_60GPa, Xylitol3_20GPa, Xylitol3_90GPa, Xylitol4_70GPa. For all structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).
Crystal data top
C5H12O5 | Dx = 1.514 Mg m−3 |
Mr = 152.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 632 reflections |
a = 8.2993 (3) Å | θ = 4.9–26.3° |
b = 8.9697 (4) Å | µ = 0.14 mm−1 |
c = 8.9693 (4) Å | T = 286 K |
V = 667.69 (5) Å3 | Prism |
Z = 4 | 0.4 × 0.3 × 0.10 mm |
F(000) = 328 | |
Data collection top
Xcalibur, Eos diffractometer | 1011 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 937 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
Detector resolution: 16.2413 pixels mm-1 | θmax = 26.9°, θmin = 3.2° |
ω scans | h = −10→3 |
Absorption correction: multi-scan CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −5→11 |
Tmin = 0.986, Tmax = 1.000 | l = −5→11 |
1283 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.0408P)2 + 0.0071P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.079 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.15 e Å−3 |
1011 reflections | Δρmin = −0.19 e Å−3 |
96 parameters | Absolute structure: Flack x determined using 233 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
0 restraints | Absolute structure parameter: 0.0 (10) |
Primary atom site location: dual | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O4 | 0.4795 (2) | 0.6418 (2) | 0.61780 (18) | 0.0280 (4) | |
H4 | 0.514387 | 0.596011 | 0.690047 | 0.042* | |
O2 | 0.8644 (2) | 0.5668 (2) | 0.3147 (2) | 0.0296 (5) | |
H2 | 0.897570 | 0.651349 | 0.331163 | 0.044* | |
O3 | 0.5694 (2) | 0.7090 (2) | 0.32032 (19) | 0.0283 (4) | |
H3 | 0.577965 | 0.708510 | 0.229246 | 0.042* | |
O1 | 0.9278 (2) | 0.3289 (2) | 0.5217 (2) | 0.0301 (5) | |
H1 | 0.988150 | 0.400148 | 0.509194 | 0.045* | |
O5 | 0.1631 (2) | 0.5337 (2) | 0.5436 (2) | 0.0327 (5) | |
H5 | 0.137266 | 0.611194 | 0.585771 | 0.049* | |
C3 | 0.5776 (3) | 0.5587 (3) | 0.3754 (3) | 0.0230 (5) | |
H3A | 0.551375 | 0.490747 | 0.293346 | 0.028* | |
C2 | 0.7508 (3) | 0.5253 (3) | 0.4276 (3) | 0.0218 (5) | |
H2A | 0.773369 | 0.581104 | 0.519241 | 0.026* | |
C1 | 0.7742 (3) | 0.3604 (3) | 0.4558 (3) | 0.0267 (6) | |
H1A | 0.689612 | 0.324989 | 0.521509 | 0.032* | |
H1B | 0.765049 | 0.306939 | 0.362197 | 0.032* | |
C4 | 0.4518 (3) | 0.5394 (3) | 0.4966 (3) | 0.0232 (6) | |
H4A | 0.458525 | 0.437329 | 0.535114 | 0.028* | |
C5 | 0.2835 (3) | 0.5647 (4) | 0.4349 (3) | 0.0292 (6) | |
H5A | 0.273366 | 0.667466 | 0.402428 | 0.035* | |
H5B | 0.267020 | 0.501030 | 0.348850 | 0.035* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.0318 (9) | 0.0276 (11) | 0.0247 (8) | 0.0045 (8) | −0.0049 (8) | −0.0031 (8) |
O2 | 0.0265 (9) | 0.0273 (11) | 0.0351 (10) | −0.0019 (8) | 0.0082 (8) | −0.0009 (9) |
O3 | 0.0336 (9) | 0.0211 (11) | 0.0303 (9) | 0.0011 (8) | −0.0012 (9) | 0.0025 (8) |
O1 | 0.0221 (8) | 0.0240 (11) | 0.0442 (10) | 0.0014 (8) | −0.0024 (9) | 0.0020 (9) |
O5 | 0.0227 (9) | 0.0292 (12) | 0.0463 (11) | −0.0022 (9) | 0.0058 (9) | −0.0066 (9) |
C3 | 0.0236 (11) | 0.0170 (13) | 0.0284 (12) | 0.0004 (11) | −0.0011 (11) | −0.0037 (11) |
C2 | 0.0205 (11) | 0.0200 (14) | 0.0247 (11) | −0.0005 (11) | 0.0033 (10) | −0.0016 (11) |
C1 | 0.0200 (11) | 0.0218 (15) | 0.0383 (15) | −0.0003 (11) | −0.0011 (11) | −0.0025 (13) |
C4 | 0.0227 (12) | 0.0182 (14) | 0.0287 (13) | 0.0016 (10) | −0.0017 (11) | −0.0036 (11) |
C5 | 0.0234 (12) | 0.0324 (17) | 0.0316 (13) | 0.0004 (11) | −0.0011 (11) | −0.0054 (13) |
Geometric parameters (Å, º) top
O4—C4 | 1.441 (3) | C3—C2 | 1.541 (3) |
O2—C2 | 1.433 (3) | C3—C4 | 1.517 (3) |
O3—C3 | 1.437 (3) | C2—C1 | 1.513 (4) |
O1—C1 | 1.433 (3) | C4—C5 | 1.520 (3) |
O5—C5 | 1.424 (3) | | |
| | | |
O3—C3—C2 | 109.3 (2) | O1—C1—C2 | 112.1 (2) |
O3—C3—C4 | 108.71 (19) | O4—C4—C3 | 111.0 (2) |
C4—C3—C2 | 113.69 (19) | O4—C4—C5 | 109.0 (2) |
O2—C2—C3 | 110.40 (19) | C3—C4—C5 | 110.76 (19) |
O2—C2—C1 | 106.7 (2) | O5—C5—C4 | 111.5 (2) |
C1—C2—C3 | 111.1 (2) | | |
Crystal data top
C5H12O5 | Dx = 1.546 Mg m−3 |
Mr = 152.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 1465 reflections |
a = 8.2694 (3) Å | θ = 4.1–25.9° |
b = 8.9403 (12) Å | µ = 0.14 mm−1 |
c = 8.8438 (9) Å | T = 296 K |
V = 653.83 (11) Å3 | Prism |
Z = 4 | 0.15 × 0.11 × 0.1 mm |
F(000) = 328 | |
Data collection top
Xcalibur, Eos diffractometer | θmax = 26.8°, θmin = 4.1° |
2431 measured reflections | h = −9→10 |
547 independent reflections | k = −7→7 |
504 reflections with I > 2σ(I) | l = −8→8 |
Rint = 0.020 | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.024 | w = 1/[σ2(Fo2) + (0.0314P)2 + 0.0769P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.057 | (Δ/σ)max < 0.001 |
S = 1.12 | Δρmax = 0.11 e Å−3 |
547 reflections | Δρmin = −0.10 e Å−3 |
94 parameters | Absolute structure: Flack x determined using 194 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
0 restraints | Absolute structure parameter: 0.1 (8) |
Primary atom site location: dual | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O4 | 0.4768 (3) | 0.6426 (4) | 0.6173 (4) | 0.0280 (9) | |
H4 | 0.504621 | 0.596658 | 0.693252 | 0.042* | |
O2 | 0.8629 (2) | 0.5686 (3) | 0.3104 (3) | 0.0292 (9) | |
H2 | 0.907208 | 0.646858 | 0.335362 | 0.044* | |
O3 | 0.5666 (3) | 0.7109 (4) | 0.3165 (3) | 0.0286 (10) | |
H3 | 0.572846 | 0.710243 | 0.223981 | 0.043* | |
O1 | 0.9266 (3) | 0.3265 (4) | 0.5152 (3) | 0.0290 (9) | |
H1 | 0.985812 | 0.399842 | 0.508482 | 0.044* | |
O5 | 0.1595 (3) | 0.5328 (4) | 0.5423 (3) | 0.0320 (9) | |
H5 | 0.134857 | 0.610215 | 0.586339 | 0.048* | |
C3 | 0.5756 (3) | 0.5601 (6) | 0.3723 (5) | 0.0237 (12) | |
H3A | 0.549441 | 0.492366 | 0.288713 | 0.028* | |
C2 | 0.7489 (4) | 0.5250 (6) | 0.4254 (5) | 0.0212 (11) | |
H2A | 0.771707 | 0.579782 | 0.518914 | 0.025* | |
C1 | 0.7721 (4) | 0.3609 (6) | 0.4515 (5) | 0.0285 (14) | |
H1A | 0.688172 | 0.325124 | 0.519073 | 0.034* | |
H1B | 0.760582 | 0.308459 | 0.356124 | 0.034* | |
C4 | 0.4492 (3) | 0.5383 (7) | 0.4952 (5) | 0.0224 (12) | |
H4A | 0.456593 | 0.435968 | 0.534291 | 0.027* | |
C5 | 0.2805 (3) | 0.5642 (6) | 0.4317 (5) | 0.0278 (12) | |
H5A | 0.270513 | 0.667357 | 0.398918 | 0.033* | |
H5B | 0.264091 | 0.500399 | 0.344298 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.0318 (12) | 0.027 (5) | 0.026 (4) | 0.0047 (13) | −0.0059 (11) | −0.0034 (12) |
O2 | 0.0241 (10) | 0.032 (4) | 0.032 (3) | −0.0061 (12) | 0.0086 (11) | −0.0023 (11) |
O3 | 0.0325 (12) | 0.030 (4) | 0.024 (3) | 0.0015 (13) | −0.0030 (13) | 0.0024 (13) |
O1 | 0.0223 (11) | 0.021 (4) | 0.044 (3) | 0.0035 (12) | −0.0023 (12) | −0.0014 (12) |
O5 | 0.0226 (11) | 0.034 (4) | 0.039 (3) | −0.0038 (14) | 0.0055 (12) | −0.0057 (13) |
C3 | 0.0217 (15) | 0.015 (6) | 0.034 (4) | 0.0011 (17) | −0.0008 (15) | −0.0025 (18) |
C2 | 0.0208 (13) | 0.020 (5) | 0.022 (4) | −0.0014 (18) | 0.0028 (14) | −0.0007 (16) |
C1 | 0.0204 (15) | 0.028 (7) | 0.037 (5) | −0.0015 (19) | −0.0021 (16) | −0.0007 (18) |
C4 | 0.0210 (14) | 0.021 (6) | 0.026 (4) | −0.0015 (18) | −0.0008 (16) | −0.0053 (18) |
C5 | 0.0220 (15) | 0.033 (6) | 0.028 (4) | 0.0021 (18) | −0.0017 (15) | −0.0026 (18) |
Geometric parameters (Å, º) top
O4—C4 | 1.445 (5) | C3—C2 | 1.540 (4) |
O2—C2 | 1.441 (4) | C3—C4 | 1.520 (6) |
O3—C3 | 1.437 (5) | C2—C1 | 1.497 (7) |
O1—C1 | 1.430 (4) | C4—C5 | 1.522 (4) |
O5—C5 | 1.427 (4) | | |
| | | |
O3—C3—C2 | 110.1 (3) | O1—C1—C2 | 112.7 (3) |
O3—C3—C4 | 109.3 (4) | O4—C4—C3 | 110.1 (4) |
C4—C3—C2 | 113.3 (3) | O4—C4—C5 | 108.8 (3) |
O2—C2—C3 | 109.8 (3) | C3—C4—C5 | 110.3 (4) |
O2—C2—C1 | 106.9 (3) | O5—C5—C4 | 111.1 (4) |
C1—C2—C3 | 111.5 (4) | | |
Crystal data top
C5H12O5 | F(000) = 328 |
Mr = 152.15 | Dx = 1.575 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2305 (2) Å | Cell parameters from 1323 reflections |
b = 8.8992 (11) Å | θ = 4.1–25.9° |
c = 8.7624 (8) Å | µ = 0.14 mm−1 |
V = 641.80 (10) Å3 | T = 296 K |
Z = 4 | Prism |
Data collection top
Multiwire proportional diffractometer | Rint = 0.020 |
Graphite monochromator | θmax = 26.2°, θmin = 4.1° |
phi and ω scans | h = −10→10 |
2149 measured reflections | k = −7→7 |
482 independent reflections | l = −8→8 |
456 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.024 | w = 1/[σ2(Fo2) + (0.0409P)2 + 0.0191P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.060 | (Δ/σ)max < 0.001 |
S = 1.13 | Δρmax = 0.10 e Å−3 |
482 reflections | Δρmin = −0.11 e Å−3 |
96 parameters | Absolute structure: Flack x determined using 176 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
0 restraints | Absolute structure parameter: 0.4 (8) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O4 | 0.4754 (3) | 0.6430 (5) | 0.6178 (4) | 0.0253 (10) | |
H4 | 0.508716 | 0.597733 | 0.692999 | 0.038* | |
O2 | 0.8625 (3) | 0.5690 (4) | 0.3075 (4) | 0.0272 (10) | |
H2 | 0.893884 | 0.654837 | 0.324389 | 0.041* | |
O3 | 0.5652 (3) | 0.7119 (4) | 0.3146 (3) | 0.0266 (10) | |
H3 | 0.576758 | 0.711897 | 0.221625 | 0.040* | |
O1 | 0.9268 (3) | 0.3255 (4) | 0.5111 (3) | 0.0274 (9) | |
H1 | 0.986817 | 0.398527 | 0.502493 | 0.041* | |
O5 | 0.1578 (3) | 0.5321 (4) | 0.5417 (4) | 0.0294 (9) | |
H5 | 0.127580 | 0.610417 | 0.581931 | 0.044* | |
C3 | 0.5744 (3) | 0.5614 (5) | 0.3703 (5) | 0.0220 (13) | |
H3A | 0.547955 | 0.493832 | 0.285584 | 0.026* | |
C2 | 0.7483 (4) | 0.5250 (7) | 0.4231 (5) | 0.0200 (11) | |
H2A | 0.771668 | 0.579576 | 0.517760 | 0.024* | |
C1 | 0.7708 (4) | 0.3606 (6) | 0.4489 (6) | 0.0266 (14) | |
H1A | 0.687285 | 0.324935 | 0.518147 | 0.032* | |
H1B | 0.757609 | 0.308018 | 0.352750 | 0.032* | |
C4 | 0.4481 (4) | 0.5376 (7) | 0.4945 (6) | 0.0218 (14) | |
H4A | 0.455873 | 0.434647 | 0.533447 | 0.026* | |
C5 | 0.2788 (3) | 0.5646 (6) | 0.4307 (5) | 0.0255 (13) | |
H5A | 0.268968 | 0.668580 | 0.398846 | 0.031* | |
H5B | 0.262191 | 0.501479 | 0.341802 | 0.031* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.0286 (12) | 0.019 (5) | 0.029 (4) | 0.0046 (13) | −0.0061 (11) | −0.0036 (13) |
O2 | 0.0233 (11) | 0.023 (5) | 0.035 (3) | −0.0047 (13) | 0.0078 (11) | −0.0010 (11) |
O3 | 0.0300 (11) | 0.028 (5) | 0.022 (3) | 0.0033 (14) | −0.0034 (13) | 0.0032 (12) |
O1 | 0.0209 (10) | 0.020 (5) | 0.041 (4) | 0.0020 (13) | −0.0034 (12) | 0.0011 (11) |
O5 | 0.0208 (12) | 0.029 (4) | 0.038 (3) | −0.0023 (15) | 0.0060 (12) | −0.0055 (13) |
C3 | 0.0194 (15) | 0.016 (6) | 0.030 (5) | 0.0008 (19) | −0.0009 (15) | −0.0028 (18) |
C2 | 0.0179 (13) | 0.027 (6) | 0.015 (4) | −0.001 (2) | 0.0029 (14) | −0.0007 (16) |
C1 | 0.0190 (15) | 0.034 (7) | 0.027 (5) | 0.000 (2) | −0.0010 (16) | −0.0019 (17) |
C4 | 0.0211 (15) | 0.024 (7) | 0.020 (5) | −0.001 (2) | −0.0014 (17) | −0.0050 (18) |
C5 | 0.0198 (15) | 0.028 (7) | 0.029 (5) | 0.0012 (19) | −0.0009 (14) | −0.0031 (17) |
Geometric parameters (Å, º) top
O4—C4 | 1.448 (6) | C3—C2 | 1.539 (5) |
O2—C2 | 1.436 (4) | C3—C4 | 1.519 (6) |
O3—C3 | 1.428 (5) | C2—C1 | 1.493 (8) |
O1—C1 | 1.429 (4) | C4—C5 | 1.521 (5) |
O5—C5 | 1.422 (5) | | |
| | | |
O3—C3—C2 | 110.5 (3) | O1—C1—C2 | 112.6 (3) |
O3—C3—C4 | 109.8 (4) | O4—C4—C3 | 109.7 (4) |
C4—C3—C2 | 113.0 (4) | O4—C4—C5 | 108.3 (4) |
O2—C2—C3 | 109.8 (3) | C3—C4—C5 | 110.0 (4) |
O2—C2—C1 | 107.0 (4) | O5—C5—C4 | 111.0 (4) |
C1—C2—C3 | 111.6 (4) | | |
Crystal data top
C5H12O5 | Dx = 1.586 Mg m−3 |
Mr = 152.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 189 reflections |
a = 8.2213 (4) Å | θ = 5.5–24.8° |
b = 8.883 (2) Å | µ = 0.14 mm−1 |
c = 8.7242 (17) Å | T = 296 K |
V = 637.1 (2) Å3 | Prism |
Z = 4 | 0.15 × 0.11 × 0.1 mm |
F(000) = 328 | |
Data collection top
Multiwire proportional diffractometer | Rint = 0.007 |
Graphite monochromator | θmax = 26.0°, θmin = 5.5° |
phi and ω scans | h = −9→9 |
305 measured reflections | k = −6→6 |
280 independent reflections | l = −7→7 |
276 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.023 | w = 1/[σ2(Fo2) + (0.0208P)2 + 0.2263P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.052 | (Δ/σ)max < 0.001 |
S = 1.21 | Δρmax = 0.07 e Å−3 |
280 reflections | Δρmin = −0.07 e Å−3 |
96 parameters | Absolute structure: Flack x determined using 115 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
20 restraints | Absolute structure parameter: 2.1 (10) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O4 | 0.4748 (7) | 0.6426 (12) | 0.6184 (9) | 0.028 (2) | |
H4 | 0.510400 | 0.597774 | 0.693381 | 0.041* | |
O2 | 0.8625 (7) | 0.5696 (10) | 0.3065 (10) | 0.027 (2) | |
H2 | 0.888744 | 0.657846 | 0.318582 | 0.040* | |
O3 | 0.5644 (8) | 0.7123 (11) | 0.3145 (8) | 0.026 (4) | |
H3 | 0.573565 | 0.712930 | 0.220932 | 0.039* | |
O1 | 0.9269 (7) | 0.3250 (9) | 0.5083 (8) | 0.027 (2) | |
H1 | 0.987304 | 0.398097 | 0.500880 | 0.041* | |
O5 | 0.1570 (7) | 0.5308 (10) | 0.5411 (9) | 0.027 (3) | |
H5 | 0.125146 | 0.609229 | 0.580615 | 0.041* | |
C3 | 0.5736 (10) | 0.5601 (17) | 0.3694 (13) | 0.022 (4) | |
H3A | 0.548118 | 0.492252 | 0.284127 | 0.026* | |
C2 | 0.7473 (10) | 0.5271 (17) | 0.4231 (12) | 0.020 (4) | |
H2A | 0.770039 | 0.581863 | 0.518223 | 0.024* | |
C1 | 0.7705 (10) | 0.3620 (17) | 0.4476 (13) | 0.025 (4) | |
H1A | 0.687389 | 0.325888 | 0.517427 | 0.030* | |
H1B | 0.755976 | 0.310302 | 0.350592 | 0.030* | |
C4 | 0.4478 (8) | 0.5364 (16) | 0.4942 (14) | 0.019 (2) | |
H4A | 0.455285 | 0.433242 | 0.533457 | 0.022* | |
C5 | 0.2777 (7) | 0.5642 (14) | 0.4298 (11) | 0.024 (4) | |
H5A | 0.267969 | 0.668577 | 0.398554 | 0.028* | |
H5B | 0.261096 | 0.501532 | 0.340058 | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.029 (3) | 0.021 (12) | 0.033 (11) | 0.003 (3) | −0.005 (3) | −0.007 (4) |
O2 | 0.026 (3) | 0.026 (4) | 0.029 (4) | −0.002 (3) | 0.008 (2) | 0.001 (3) |
O3 | 0.032 (3) | 0.034 (18) | 0.012 (11) | 0.000 (4) | 0.001 (3) | 0.004 (4) |
O1 | 0.020 (3) | 0.011 (13) | 0.051 (10) | 0.000 (3) | −0.003 (3) | −0.004 (4) |
O5 | 0.021 (3) | 0.017 (13) | 0.043 (9) | −0.005 (4) | 0.007 (3) | −0.006 (3) |
C3 | 0.018 (4) | 0.012 (14) | 0.036 (12) | −0.001 (5) | 0.002 (4) | 0.003 (6) |
C2 | 0.022 (5) | 0.01 (2) | 0.023 (15) | −0.007 (6) | 0.009 (4) | −0.001 (4) |
C1 | 0.015 (4) | 0.03 (2) | 0.030 (17) | 0.000 (5) | −0.002 (3) | −0.002 (6) |
C4 | 0.018 (3) | 0.019 (3) | 0.019 (3) | 0.001 (2) | −0.0006 (19) | 0.000 (2) |
C5 | 0.017 (4) | 0.03 (2) | 0.023 (15) | −0.002 (5) | 0.001 (3) | −0.003 (5) |
Geometric parameters (Å, º) top
O4—C4 | 1.454 (13) | C3—C2 | 1.531 (12) |
O2—C2 | 1.440 (11) | C3—C4 | 1.517 (15) |
O3—C3 | 1.437 (13) | C2—C1 | 1.494 (17) |
O1—C1 | 1.429 (9) | C4—C5 | 1.527 (11) |
O5—C5 | 1.420 (10) | | |
| | | |
O3—C3—C2 | 109.3 (10) | O1—C1—C2 | 113.2 (10) |
O3—C3—C4 | 109.5 (9) | O4—C4—C3 | 109.9 (10) |
C4—C3—C2 | 113.0 (8) | O4—C4—C5 | 108.0 (8) |
O2—C2—C3 | 110.3 (8) | C3—C4—C5 | 109.7 (10) |
O2—C2—C1 | 105.9 (9) | O5—C5—C4 | 110.8 (8) |
C1—C2—C3 | 110.5 (11) | | |
Crystal data top
C5H12O5 | Dx = 1.603 Mg m−3 |
Mr = 152.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 805 reflections |
a = 8.204 (2) Å | θ = 3.3–20.3° |
b = 8.854 (2) Å | µ = 0.14 mm−1 |
c = 8.6809 (7) Å | T = 296 K |
V = 630.6 (2) Å3 | Prism |
Z = 4 | 0.15 × 0.11 × 0.1 mm |
F(000) = 328 | |
Data collection top
Multiwire proportional diffractometer | Rint = 0.065 |
Graphite monochromator | θmax = 27.3°, θmin = 3.3° |
phi and ω scans | h = −7→7 |
2619 measured reflections | k = −8→8 |
467 independent reflections | l = −11→11 |
377 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0381P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.077 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 0.11 e Å−3 |
467 reflections | Δρmin = −0.13 e Å−3 |
94 parameters | Absolute structure: Flack x determined using 141 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
7 restraints | Absolute structure parameter: −1.4 (10) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O4 | 0.4743 (7) | 0.6414 (7) | 0.6198 (4) | 0.0327 (16) | |
H4 | 0.517113 | 0.595187 | 0.690941 | 0.049* | |
O2 | 0.8621 (7) | 0.5708 (5) | 0.3055 (4) | 0.0345 (15) | |
H2 | 0.908398 | 0.648302 | 0.333141 | 0.052* | |
O3 | 0.5648 (8) | 0.7135 (6) | 0.3134 (4) | 0.0345 (14) | |
H3 | 0.571989 | 0.713761 | 0.219157 | 0.052* | |
O1 | 0.9253 (9) | 0.3258 (7) | 0.5080 (4) | 0.0376 (17) | |
H1 | 0.988519 | 0.395549 | 0.490910 | 0.056* | |
O5 | 0.1573 (8) | 0.5325 (7) | 0.5401 (5) | 0.0366 (17) | |
H5 | 0.139862 | 0.607349 | 0.593221 | 0.055* | |
C3 | 0.5752 (11) | 0.5614 (9) | 0.3688 (6) | 0.028 (2) | |
H3A | 0.548859 | 0.493888 | 0.282871 | 0.034* | |
C2 | 0.7473 (12) | 0.5268 (9) | 0.4195 (7) | 0.030 (2) | |
H2A | 0.770415 | 0.581089 | 0.515373 | 0.035* | |
C1 | 0.7706 (12) | 0.3607 (10) | 0.4455 (8) | 0.032 (2) | |
H1A | 0.686646 | 0.324602 | 0.515009 | 0.039* | |
H1B | 0.757769 | 0.308051 | 0.348256 | 0.039* | |
C4 | 0.4455 (11) | 0.5393 (9) | 0.4927 (6) | 0.0286 (19) | |
H4A | 0.451795 | 0.435240 | 0.530780 | 0.034* | |
C5 | 0.2780 (11) | 0.5662 (9) | 0.4297 (8) | 0.032 (2) | |
H5A | 0.267959 | 0.671074 | 0.398625 | 0.038* | |
H5B | 0.261608 | 0.503742 | 0.339215 | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.015 (9) | 0.051 (7) | 0.0315 (17) | 0.004 (2) | −0.007 (2) | −0.003 (2) |
O2 | 0.019 (8) | 0.044 (7) | 0.041 (2) | −0.003 (2) | 0.004 (3) | −0.002 (2) |
O3 | 0.036 (8) | 0.030 (7) | 0.0377 (18) | 0.000 (2) | −0.004 (3) | −0.001 (2) |
O1 | 0.010 (9) | 0.049 (8) | 0.053 (2) | 0.002 (2) | −0.007 (3) | 0.003 (3) |
O5 | 0.008 (10) | 0.055 (8) | 0.046 (2) | −0.006 (2) | 0.007 (3) | −0.004 (3) |
C3 | 0.008 (12) | 0.043 (10) | 0.032 (3) | 0.000 (3) | 0.004 (4) | −0.002 (4) |
C2 | 0.016 (9) | 0.044 (9) | 0.029 (3) | −0.001 (4) | 0.000 (4) | −0.007 (3) |
C1 | 0.027 (13) | 0.031 (10) | 0.038 (3) | 0.003 (4) | 0.002 (4) | −0.003 (4) |
C4 | 0.027 (12) | 0.026 (9) | 0.033 (3) | −0.001 (3) | −0.001 (4) | −0.001 (3) |
C5 | 0.032 (12) | 0.027 (10) | 0.036 (3) | 0.001 (3) | −0.007 (4) | −0.004 (3) |
Geometric parameters (Å, º) top
O4—C4 | 1.446 (8) | C3—C2 | 1.510 (10) |
O2—C2 | 1.420 (10) | C3—C4 | 1.526 (10) |
O3—C3 | 1.433 (8) | C2—C1 | 1.500 (11) |
O1—C1 | 1.415 (9) | C4—C5 | 1.498 (10) |
O5—C5 | 1.410 (8) | | |
| | | |
O3—C3—C2 | 110.2 (6) | O1—C1—C2 | 112.7 (7) |
O3—C3—C4 | 108.4 (5) | O4—C4—C3 | 110.1 (6) |
C2—C3—C4 | 114.9 (6) | O4—C4—C5 | 109.2 (6) |
O2—C2—C3 | 111.2 (5) | C5—C4—C3 | 111.2 (5) |
O2—C2—C1 | 106.8 (6) | O5—C5—C4 | 111.2 (5) |
C1—C2—C3 | 111.2 (7) | | |
Crystal data top
C5H12O5 | Dx = 1.646 Mg m−3 |
Mr = 152.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 1044 reflections |
a = 8.1540 (5) Å | θ = 3.3–20.5° |
b = 8.7964 (16) Å | µ = 0.15 mm−1 |
c = 8.5610 (19) Å | T = 296 K |
V = 614.04 (18) Å3 | Prism |
Z = 4 | 0.15 × 0.11 × 0.1 mm |
F(000) = 328 | |
Data collection top
Multiwire proportional diffractometer | Rint = 0.059 |
Graphite monochromator | θmax = 27.0°, θmin = 3.3° |
phi and ω scans | h = −10→10 |
2583 measured reflections | k = −8→8 |
502 independent reflections | l = −7→7 |
405 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.025P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.063 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 0.11 e Å−3 |
502 reflections | Δρmin = −0.10 e Å−3 |
96 parameters | Absolute structure: Flack x determined using 139 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
14 restraints | Absolute structure parameter: −3.0 (10) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O4 | 0.4724 (4) | 0.6423 (7) | 0.6195 (7) | 0.0257 (14) | |
H4 | 0.518543 | 0.596491 | 0.690468 | 0.039* | |
O2 | 0.8614 (4) | 0.5715 (5) | 0.3015 (5) | 0.0269 (14) | |
H2 | 0.901689 | 0.653911 | 0.324836 | 0.040* | |
O3 | 0.5638 (6) | 0.7170 (5) | 0.3097 (6) | 0.0264 (15) | |
H3 | 0.560309 | 0.717633 | 0.213970 | 0.040* | |
O1 | 0.9274 (4) | 0.3227 (5) | 0.5013 (6) | 0.0275 (14) | |
H1 | 0.983901 | 0.399733 | 0.504794 | 0.041* | |
O5 | 0.1533 (4) | 0.5309 (5) | 0.5393 (6) | 0.0288 (14) | |
H5 | 0.126878 | 0.609002 | 0.585107 | 0.043* | |
C3 | 0.5729 (6) | 0.5629 (8) | 0.3641 (8) | 0.0215 (18) | |
H3A | 0.546704 | 0.495353 | 0.276591 | 0.026* | |
C2 | 0.7458 (6) | 0.5275 (8) | 0.4184 (8) | 0.0180 (17) | |
H2A | 0.768720 | 0.581828 | 0.515958 | 0.022* | |
C1 | 0.7682 (5) | 0.3600 (9) | 0.4425 (8) | 0.025 (2) | |
H1A | 0.685852 | 0.323754 | 0.515243 | 0.030* | |
H1B | 0.751366 | 0.307997 | 0.343837 | 0.030* | |
C4 | 0.4440 (6) | 0.5399 (9) | 0.4907 (11) | 0.0200 (19) | |
H4A | 0.451488 | 0.435129 | 0.529072 | 0.024* | |
C5 | 0.2743 (5) | 0.5651 (8) | 0.4254 (8) | 0.027 (2) | |
H5A | 0.262984 | 0.670208 | 0.392702 | 0.032* | |
H5B | 0.258326 | 0.500962 | 0.334493 | 0.032* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.028 (2) | 0.028 (8) | 0.021 (8) | 0.005 (2) | −0.010 (3) | −0.002 (2) |
O2 | 0.025 (2) | 0.025 (6) | 0.031 (7) | −0.004 (2) | 0.004 (2) | −0.0022 (19) |
O3 | 0.031 (2) | 0.023 (6) | 0.026 (7) | 0.002 (2) | −0.006 (3) | 0.001 (2) |
O1 | 0.024 (2) | 0.021 (6) | 0.037 (7) | 0.000 (2) | −0.007 (2) | −0.001 (2) |
O5 | 0.0212 (18) | 0.032 (5) | 0.033 (6) | −0.002 (2) | 0.007 (2) | −0.006 (2) |
C3 | 0.023 (3) | 0.015 (7) | 0.027 (8) | −0.002 (3) | 0.003 (3) | 0.001 (3) |
C2 | 0.015 (2) | 0.014 (8) | 0.025 (10) | 0.000 (3) | 0.005 (3) | 0.001 (3) |
C1 | 0.014 (3) | 0.027 (9) | 0.035 (11) | −0.001 (3) | 0.000 (3) | 0.005 (3) |
C4 | 0.019 (3) | 0.015 (8) | 0.026 (9) | −0.001 (3) | −0.006 (3) | 0.001 (4) |
C5 | 0.020 (3) | 0.012 (9) | 0.048 (11) | 0.002 (3) | 0.001 (3) | −0.008 (3) |
Geometric parameters (Å, º) top
O4—C4 | 1.443 (9) | C3—C2 | 1.516 (6) |
O2—C2 | 1.428 (7) | C3—C4 | 1.523 (10) |
O3—C3 | 1.435 (6) | C2—C1 | 1.499 (9) |
O1—C1 | 1.430 (6) | C4—C5 | 1.509 (7) |
O5—C5 | 1.420 (7) | | |
| | | |
O3—C3—C2 | 109.9 (5) | O1—C1—C2 | 112.6 (5) |
O3—C3—C4 | 108.7 (5) | O4—C4—C3 | 110.5 (6) |
C2—C3—C4 | 113.4 (5) | O4—C4—C5 | 109.8 (6) |
O2—C2—C3 | 110.1 (5) | C5—C4—C3 | 110.5 (7) |
O2—C2—C1 | 106.4 (5) | O5—C5—C4 | 110.6 (6) |
C1—C2—C3 | 110.9 (5) | | |
Crystal data top
C5H12O5 | Dx = 1.684 Mg m−3 |
Mr = 152.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 402 reflections |
a = 8.105 (9) Å | θ = 3.4–18.4° |
b = 8.752 (6) Å | µ = 0.15 mm−1 |
c = 8.462 (2) Å | T = 296 K |
V = 600.3 (8) Å3 | Prism |
Z = 4 | 0.15 × 0.11 × 0.1 mm |
F(000) = 328 | |
Data collection top
Multiwire proportional diffractometer | Rint = 0.120 |
Graphite monochromator | θmax = 26.8°, θmin = 3.4° |
phi and ω scans | h = −7→7 |
2462 measured reflections | k = −8→8 |
391 independent reflections | l = −10→10 |
256 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.054 | w = 1/[σ2(Fo2) + (0.0731P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.138 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.18 e Å−3 |
391 reflections | Δρmin = −0.15 e Å−3 |
95 parameters | Absolute structure: Flack x determined using 84 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
60 restraints | Absolute structure parameter: −5.6 (10) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O4 | 0.4713 (17) | 0.6411 (15) | 0.6202 (9) | 0.049 (4) | |
H4 | 0.508617 | 0.591239 | 0.694048 | 0.073* | |
O2 | 0.8612 (19) | 0.5724 (16) | 0.2970 (12) | 0.048 (4) | |
H2 | 0.912272 | 0.648148 | 0.326537 | 0.072* | |
O3 | 0.5648 (18) | 0.7185 (14) | 0.3064 (10) | 0.049 (3) | |
H3 | 0.571588 | 0.718492 | 0.209672 | 0.073* | |
O1 | 0.9293 (19) | 0.3221 (14) | 0.4947 (11) | 0.050 (4) | |
H1 | 0.988873 | 0.397776 | 0.492795 | 0.075* | |
O5 | 0.1512 (18) | 0.5312 (17) | 0.5375 (12) | 0.055 (4) | |
H5 | 0.148226 | 0.598721 | 0.604614 | 0.082* | |
C3 | 0.575 (3) | 0.566 (2) | 0.3631 (16) | 0.042 (4) | |
H3A | 0.548992 | 0.498491 | 0.274501 | 0.051* | |
C2 | 0.747 (3) | 0.529 (2) | 0.4148 (19) | 0.047 (4) | |
H2A | 0.771658 | 0.583747 | 0.512999 | 0.057* | |
C1 | 0.767 (3) | 0.363 (2) | 0.441 (2) | 0.048 (5) | |
H1A | 0.686158 | 0.329015 | 0.518042 | 0.057* | |
H1B | 0.744030 | 0.309376 | 0.342459 | 0.057* | |
C4 | 0.443 (3) | 0.543 (2) | 0.4882 (13) | 0.043 (4) | |
H4A | 0.449823 | 0.436775 | 0.525173 | 0.052* | |
C5 | 0.274 (3) | 0.568 (2) | 0.4211 (17) | 0.045 (5) | |
H5A | 0.261785 | 0.673926 | 0.389259 | 0.054* | |
H5B | 0.258392 | 0.504301 | 0.328502 | 0.054* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.015 (18) | 0.080 (14) | 0.052 (4) | 0.002 (6) | −0.013 (7) | −0.001 (6) |
O2 | 0.024 (14) | 0.062 (14) | 0.059 (6) | 0.000 (5) | 0.008 (7) | 0.002 (6) |
O3 | 0.023 (15) | 0.069 (13) | 0.053 (5) | 0.002 (5) | −0.005 (7) | 0.004 (5) |
O1 | 0.010 (18) | 0.061 (16) | 0.079 (6) | −0.011 (6) | −0.012 (9) | 0.007 (7) |
O5 | 0.012 (16) | 0.086 (16) | 0.066 (5) | −0.005 (6) | 0.005 (7) | −0.006 (6) |
C3 | 0.016 (13) | 0.070 (12) | 0.042 (6) | 0.004 (7) | 0.001 (9) | −0.001 (8) |
C2 | 0.012 (13) | 0.067 (13) | 0.063 (9) | 0.004 (8) | −0.002 (9) | 0.008 (8) |
C1 | 0.009 (19) | 0.062 (13) | 0.072 (11) | −0.008 (8) | 0.002 (10) | 0.005 (9) |
C4 | 0.010 (13) | 0.076 (16) | 0.044 (7) | 0.003 (7) | −0.006 (7) | 0.000 (7) |
C5 | 0.012 (14) | 0.088 (18) | 0.036 (8) | 0.007 (8) | −0.005 (7) | 0.001 (7) |
Geometric parameters (Å, º) top
O4—C4 | 1.430 (17) | C3—C2 | 1.49 (2) |
O2—C2 | 1.41 (2) | C3—C4 | 1.52 (2) |
O3—C3 | 1.419 (18) | C2—C1 | 1.48 (3) |
O1—C1 | 1.44 (2) | C4—C5 | 1.50 (2) |
O5—C5 | 1.435 (18) | | |
| | | |
O3—C3—C2 | 111.1 (15) | O1—C1—C2 | 112.8 (16) |
O3—C3—C4 | 108.7 (13) | O4—C4—C3 | 110.4 (15) |
C2—C3—C4 | 115.1 (13) | O4—C4—C5 | 110.6 (15) |
O2—C2—C3 | 110.2 (15) | C5—C4—C3 | 111.2 (11) |
O2—C2—C1 | 107.3 (15) | O5—C5—C4 | 109.9 (12) |
C1—C2—C3 | 111.0 (15) | | |
Crystal data top
C5H12O5 | Dx = 1.722 Mg m−3 |
Mr = 152.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 594 reflections |
a = 8.0845 (8) Å | θ = 3.5–23.5° |
b = 8.67 (2) Å | µ = 0.16 mm−1 |
c = 8.3725 (11) Å | T = 296 K |
V = 586.9 (14) Å3 | Prism |
Z = 4 | 0.15 × 0.11 × 0.1 mm |
F(000) = 328 | |
Data collection top
Multiwire proportional diffractometer | Rint = 0.073 |
Graphite monochromator | θmax = 27.5°, θmin = 3.5° |
phi and ω scans | h = −10→10 |
2371 measured reflections | k = −2→2 |
283 independent reflections | l = −10→10 |
192 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0439P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.088 | (Δ/σ)max < 0.001 |
S = 1.22 | Δρmax = 0.10 e Å−3 |
283 reflections | Δρmin = −0.13 e Å−3 |
94 parameters | Absolute structure: Flack x determined using 46 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
80 restraints | Absolute structure parameter: −0.2 (10) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O4 | 0.4704 (7) | 0.644 (4) | 0.6195 (7) | 0.04 (2) | |
H4 | 0.503160 | 0.591997 | 0.695134 | 0.058* | |
O2 | 0.8653 (12) | 0.576 (3) | 0.2970 (11) | 0.061 (14) | |
H2 | 0.862161 | 0.669746 | 0.282966 | 0.091* | |
O3 | 0.5607 (16) | 0.725 (3) | 0.3053 (10) | 0.055 (13) | |
H3 | 0.571186 | 0.727781 | 0.207938 | 0.082* | |
O1 | 0.9291 (8) | 0.317 (5) | 0.4915 (8) | 0.049 (17) | |
H1 | 0.987682 | 0.393721 | 0.495027 | 0.074* | |
O5 | 0.1508 (6) | 0.524 (4) | 0.5380 (7) | 0.032 (12) | |
H5 | 0.109021 | 0.601064 | 0.577296 | 0.048* | |
C3 | 0.573 (2) | 0.571 (4) | 0.3578 (16) | 0.043 (13) | |
H3A | 0.546330 | 0.502850 | 0.268194 | 0.052* | |
C2 | 0.7467 (19) | 0.534 (5) | 0.417 (2) | 0.038 (8) | |
H2A | 0.769894 | 0.586425 | 0.517754 | 0.046* | |
C1 | 0.7667 (19) | 0.358 (5) | 0.435 (2) | 0.039 (8) | |
H1A | 0.684299 | 0.320077 | 0.509157 | 0.047* | |
H1B | 0.747320 | 0.309264 | 0.332340 | 0.047* | |
C4 | 0.4432 (12) | 0.548 (8) | 0.4884 (11) | 0.036 (17) | |
H4A | 0.452471 | 0.440984 | 0.525585 | 0.043* | |
C5 | 0.2713 (8) | 0.568 (6) | 0.4201 (11) | 0.031 (7) | |
H5A | 0.254472 | 0.675243 | 0.390163 | 0.038* | |
H5B | 0.258791 | 0.505164 | 0.325229 | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.035 (3) | 0.05 (6) | 0.031 (3) | 0.007 (12) | −0.004 (3) | −0.004 (9) |
O2 | 0.032 (3) | 0.11 (4) | 0.045 (4) | −0.006 (13) | 0.012 (3) | 0.030 (13) |
O3 | 0.039 (4) | 0.09 (4) | 0.039 (5) | 0.009 (15) | −0.003 (4) | 0.019 (14) |
O1 | 0.027 (3) | 0.06 (5) | 0.056 (4) | 0.008 (15) | −0.004 (3) | −0.013 (15) |
O5 | 0.025 (2) | 0.02 (4) | 0.051 (3) | 0.009 (12) | 0.007 (3) | 0.003 (11) |
C3 | 0.026 (5) | 0.07 (4) | 0.036 (8) | 0.008 (14) | −0.005 (5) | −0.009 (16) |
C2 | 0.025 (6) | 0.05 (2) | 0.037 (8) | 0.004 (15) | 0.010 (5) | 0.006 (19) |
C1 | 0.024 (6) | 0.048 (19) | 0.045 (8) | −0.001 (12) | −0.005 (5) | −0.001 (14) |
C4 | 0.025 (5) | 0.05 (5) | 0.037 (5) | 0.018 (16) | 0.005 (4) | −0.011 (14) |
C5 | 0.024 (3) | 0.04 (2) | 0.034 (6) | 0.002 (10) | 0.003 (3) | 0.004 (11) |
Geometric parameters (Å, º) top
O4—C4 | 1.39 (5) | C3—C2 | 1.53 (3) |
O2—C2 | 1.43 (2) | C3—C4 | 1.53 (2) |
O3—C3 | 1.41 (3) | C2—C1 | 1.54 (3) |
O1—C1 | 1.442 (19) | C4—C5 | 1.513 (16) |
O5—C5 | 1.440 (17) | | |
| | | |
O3—C3—C2 | 111 (2) | O1—C1—C2 | 112 (2) |
O3—C3—C4 | 108 (3) | O4—C4—C3 | 112 (3) |
C2—C3—C4 | 111.9 (14) | O4—C4—C5 | 112 (3) |
O2—C2—C3 | 109.6 (18) | C5—C4—C3 | 110.1 (13) |
O2—C2—C1 | 105 (3) | O5—C5—C4 | 109.3 (14) |
C3—C2—C1 | 110 (2) | | |
Crystal data top
C5H12O5 | Dx = 1.742 Mg m−3 |
Mr = 152.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 594 reflections |
a = 8.0696 (15) Å | θ = 3.5–23.5° |
b = 8.65 (5) Å | µ = 0.16 mm−1 |
c = 8.309 (2) Å | T = 296 K |
V = 580 (3) Å3 | Prism |
Z = 4 | 0.15 × 0.11 × 0.1 mm |
F(000) = 328 | |
Data collection top
Multiwire proportional diffractometer | Rint = 0.088 |
Graphite monochromator | θmax = 26.9°, θmin = 4.9° |
phi and ω scans | h = −9→10 |
2078 measured reflections | k = −2→2 |
265 independent reflections | l = −10→10 |
175 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.052 | w = 1/[σ2(Fo2) + (0.0739P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.124 | (Δ/σ)max < 0.001 |
S = 1.16 | Δρmax = 0.14 e Å−3 |
265 reflections | Δρmin = −0.11 e Å−3 |
93 parameters | Absolute structure: Flack x determined using 41 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
73 restraints | Absolute structure parameter: −1.3 (10) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O4 | 0.4731 (11) | 0.643 (5) | 0.6186 (9) | 0.08 (3) | |
H4 | 0.463177 | 0.598706 | 0.688318 | 0.096* | |
O2 | 0.8636 (9) | 0.576 (4) | 0.2918 (9) | 0.04 (2) | |
H2 | 0.919502 | 0.646980 | 0.328640 | 0.066* | |
O3 | 0.5616 (18) | 0.719 (5) | 0.3024 (14) | 0.054 (18) | |
H3 | 0.568317 | 0.718183 | 0.218437 | 0.081* | |
O1 | 0.9299 (11) | 0.309 (6) | 0.4872 (16) | 0.046 (13) | |
H1 | 0.984912 | 0.386410 | 0.489691 | 0.070* | |
O5 | 0.1495 (10) | 0.531 (5) | 0.5363 (9) | 0.07 (4) | |
H5 | 0.113304 | 0.615296 | 0.565136 | 0.112* | |
C3 | 0.572 (3) | 0.570 (12) | 0.360 (2) | 0.053 (17) | |
H3A | 0.542008 | 0.501159 | 0.270632 | 0.064* | |
C2 | 0.747 (3) | 0.521 (7) | 0.415 (3) | 0.044 (16) | |
H2A | 0.772447 | 0.571712 | 0.517759 | 0.053* | |
C1 | 0.770 (3) | 0.346 (7) | 0.434 (4) | 0.058 (16) | |
H1A | 0.689330 | 0.306587 | 0.510497 | 0.070* | |
H1B | 0.749682 | 0.295683 | 0.331294 | 0.070* | |
C4 | 0.4425 (16) | 0.552 (10) | 0.4843 (16) | 0.05 (2) | |
H4A | 0.457472 | 0.446234 | 0.523515 | 0.060* | |
C5 | 0.2716 (13) | 0.553 (8) | 0.4200 (14) | 0.037 (8) | |
H5A | 0.252164 | 0.651332 | 0.366828 | 0.045* | |
H5B | 0.261756 | 0.472458 | 0.339594 | 0.045* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.052 (5) | 0.15 (8) | 0.041 (4) | 0.007 (17) | 0.005 (4) | −0.013 (12) |
O2 | 0.042 (4) | 0.04 (6) | 0.047 (4) | −0.015 (18) | 0.006 (5) | −0.033 (15) |
O3 | 0.040 (5) | 0.08 (6) | 0.045 (7) | 0.000 (17) | −0.006 (7) | 0.024 (18) |
O1 | 0.035 (5) | 0.04 (4) | 0.063 (6) | 0.003 (16) | −0.007 (5) | −0.011 (17) |
O5 | 0.033 (4) | 0.13 (12) | 0.057 (5) | −0.04 (2) | 0.005 (5) | 0.007 (17) |
C3 | 0.043 (7) | 0.08 (5) | 0.033 (10) | 0.012 (17) | −0.006 (7) | 0.026 (18) |
C2 | 0.029 (8) | 0.07 (5) | 0.037 (11) | 0.013 (17) | 0.005 (7) | 0.00 (2) |
C1 | 0.036 (8) | 0.07 (5) | 0.069 (13) | 0.009 (19) | −0.007 (8) | 0.01 (3) |
C4 | 0.036 (6) | 0.07 (7) | 0.042 (7) | 0.007 (19) | 0.001 (6) | 0.023 (18) |
C5 | 0.037 (5) | 0.04 (2) | 0.033 (8) | 0.003 (12) | 0.001 (5) | 0.003 (14) |
Geometric parameters (Å, º) top
O4—C4 | 1.39 (6) | C3—C2 | 1.54 (4) |
O2—C2 | 1.47 (4) | C3—C4 | 1.48 (3) |
O3—C3 | 1.38 (11) | C2—C1 | 1.54 (3) |
O1—C1 | 1.40 (3) | C4—C5 | 1.478 (18) |
O5—C5 | 1.393 (16) | | |
| | | |
O3—C3—C2 | 115 (5) | O1—C1—C2 | 111 (4) |
O3—C3—C4 | 107 (5) | O4—C4—C3 | 112 (4) |
C4—C3—C2 | 114 (2) | O4—C4—C5 | 117 (4) |
O2—C2—C3 | 107 (3) | C5—C4—C3 | 114.0 (14) |
O2—C2—C1 | 108 (4) | O5—C5—C4 | 114.1 (12) |
C1—C2—C3 | 114 (4) | | |
Crystal data top
C5H12O5 | Dx = 1.770 Mg m−3 |
Mr = 152.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 739 reflections |
a = 8.0108 (4) Å | θ = 4.7–24.2° |
b = 8.6270 (5) Å | µ = 0.16 mm−1 |
c = 8.263 (8) Å | T = 293 K |
V = 571.0 (6) Å3 | Prism |
Z = 4 | 0.15 × 0.11 × 0.1 mm |
F(000) = 328 | |
Data collection top
Xcalibur, Eos diffractometer | θmax = 27.0°, θmin = 4.7° |
2081 measured reflections | h = −10→9 |
303 independent reflections | k = −10→10 |
238 reflections with I > 2σ(I) | l = −2→2 |
Rint = 0.048 | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.026 | w = 1/[σ2(Fo2) + (0.0241P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.046 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.07 e Å−3 |
303 reflections | Δρmin = −0.08 e Å−3 |
96 parameters | Absolute structure: Flack x determined using 64 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
60 restraints | Absolute structure parameter: −3.5 (10) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O4 | 1.4694 (5) | 1.6442 (6) | 1.622 (2) | 0.026 (6) | |
H4 | 1.510031 | 1.594204 | 1.696222 | 0.040* | |
O2 | 1.8656 (5) | 1.5748 (3) | 1.2890 (17) | 0.020 (8) | |
H2 | 1.899050 | 1.662667 | 1.308665 | 0.030* | |
O3 | 1.5634 (10) | 1.7261 (5) | 1.300 (3) | 0.023 (11) | |
H3 | 1.543084 | 1.727618 | 1.202780 | 0.034* | |
O1 | 1.9301 (5) | 1.3162 (5) | 1.485 (3) | 0.044 (18) | |
H1 | 1.991741 | 1.391684 | 1.477023 | 0.067* | |
O5 | 1.1483 (5) | 1.5291 (4) | 1.5362 (17) | 0.034 (10) | |
H5 | 1.128590 | 1.605050 | 1.592690 | 0.051* | |
C3 | 1.5718 (6) | 1.5685 (6) | 1.355 (4) | 0.023 (8) | |
H3A | 1.544401 | 1.501675 | 1.262696 | 0.028* | |
C2 | 1.7475 (6) | 1.5307 (6) | 1.406 (3) | 0.021 (9) | |
H2A | 1.772308 | 1.583306 | 1.508720 | 0.025* | |
C1 | 1.7650 (5) | 1.3565 (6) | 1.429 (2) | 0.029 (13) | |
H1A | 1.682814 | 1.320814 | 1.506669 | 0.035* | |
H1B | 1.743434 | 1.304724 | 1.326814 | 0.035* | |
C4 | 1.4412 (7) | 1.5422 (7) | 1.483 (3) | 0.025 (7) | |
H4A | 1.449181 | 1.434525 | 1.520047 | 0.030* | |
C5 | 1.2688 (6) | 1.5686 (6) | 1.417 (3) | 0.032 (8) | |
H5A | 1.255873 | 1.676546 | 1.387129 | 0.038* | |
H5B | 1.252093 | 1.505614 | 1.321549 | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.022 (3) | 0.026 (3) | 0.03 (2) | 0.0050 (19) | −0.001 (6) | 0.006 (8) |
O2 | 0.0228 (17) | 0.0167 (19) | 0.02 (2) | −0.0019 (15) | −0.003 (6) | 0.000 (6) |
O3 | 0.027 (3) | 0.015 (2) | 0.03 (3) | 0.0012 (16) | −0.002 (8) | −0.006 (6) |
O1 | 0.011 (2) | 0.017 (2) | 0.10 (6) | 0.0035 (15) | −0.001 (7) | −0.002 (7) |
O5 | 0.0192 (19) | 0.0206 (19) | 0.06 (3) | −0.0030 (15) | 0.005 (6) | −0.008 (5) |
C3 | 0.019 (3) | 0.016 (3) | 0.04 (2) | 0.001 (2) | 0.006 (8) | 0.000 (7) |
C2 | 0.012 (2) | 0.020 (3) | 0.03 (3) | −0.002 (2) | 0.002 (7) | −0.008 (7) |
C1 | 0.012 (3) | 0.021 (3) | 0.05 (4) | 0.0020 (19) | −0.008 (7) | 0.001 (7) |
C4 | 0.023 (3) | 0.013 (3) | 0.04 (2) | −0.003 (2) | 0.006 (8) | 0.004 (7) |
C5 | 0.011 (3) | 0.023 (3) | 0.06 (3) | 0.000 (2) | 0.000 (7) | −0.011 (8) |
Geometric parameters (Å, º) top
O4—C4 | 1.46 (2) | C3—C2 | 1.506 (14) |
O2—C2 | 1.41 (2) | C3—C4 | 1.51 (3) |
O3—C3 | 1.435 (15) | C2—C1 | 1.521 (8) |
O1—C1 | 1.445 (10) | C4—C5 | 1.501 (13) |
O5—C5 | 1.418 (19) | | |
| | | |
O3—C3—C2 | 109.8 (5) | O1—C1—C2 | 111.2 (5) |
O3—C3—C4 | 109.4 (11) | O4—C4—C3 | 110.6 (10) |
C2—C3—C4 | 115 (2) | O4—C4—C5 | 109.5 (10) |
O2—C2—C3 | 112.0 (18) | C5—C4—C3 | 111.2 (18) |
O2—C2—C1 | 106.8 (10) | O5—C5—C4 | 109.9 (16) |
C3—C2—C1 | 109.6 (5) | | |
Crystal data top
C5H12O5 | Dx = 1.798 Mg m−3 |
Mr = 152.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 396 reflections |
a = 7.9846 (14) Å | θ = 3.4–23.6° |
b = 8.6043 (11) Å | µ = 0.16 mm−1 |
c = 8.179 (12) Å | T = 296 K |
V = 561.9 (9) Å3 | Prism |
Z = 4 | 0.15 × 0.11 × 0.1 mm |
F(000) = 328 | |
Data collection top
Multiwire proportional diffractometer | Rint = 0.210 |
Graphite monochromator | θmax = 27.7°, θmin = 3.5° |
phi and ω scans | h = −10→10 |
2216 measured reflections | k = −10→10 |
290 independent reflections | l = −2→2 |
160 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.083 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.13 e Å−3 |
290 reflections | Δρmin = −0.13 e Å−3 |
95 parameters | Absolute structure: Flack x determined using 34 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
86 restraints | Absolute structure parameter: 10.0 (10) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O4 | 0.4714 (16) | 0.6451 (10) | 0.618 (5) | 0.049 (16) | |
H4 | 0.490014 | 0.596054 | 0.701882 | 0.074* | |
O2 | 0.8672 (12) | 0.5756 (7) | 0.288 (5) | 0.041 (12) | |
H2 | 0.889523 | 0.667763 | 0.300782 | 0.062* | |
O3 | 0.564 (3) | 0.7269 (9) | 0.304 (6) | 0.05 (2) | |
H3 | 0.575995 | 0.728795 | 0.204394 | 0.070* | |
O1 | 0.9315 (14) | 0.3162 (12) | 0.484 (6) | 0.028 (12) | |
H1 | 0.993770 | 0.391633 | 0.476859 | 0.042* | |
O5 | 0.1509 (12) | 0.5276 (9) | 0.530 (4) | 0.035 (11) | |
H5 | 0.129472 | 0.601658 | 0.589813 | 0.053* | |
C3 | 0.5724 (16) | 0.5682 (13) | 0.361 (6) | 0.050 (16) | |
H3A | 0.541706 | 0.501972 | 0.268093 | 0.060* | |
C2 | 0.7488 (18) | 0.5293 (12) | 0.404 (8) | 0.030 (7) | |
H2A | 0.776294 | 0.577675 | 0.508707 | 0.036* | |
C1 | 0.7641 (13) | 0.3572 (11) | 0.420 (6) | 0.033 (7) | |
H1A | 0.691751 | 0.324901 | 0.482911 | 0.040* | |
H1B | 0.750006 | 0.315978 | 0.331118 | 0.040* | |
C4 | 0.4413 (19) | 0.5428 (15) | 0.491 (6) | 0.047 (16) | |
H4A | 0.449412 | 0.435942 | 0.531579 | 0.056* | |
C5 | 0.2675 (16) | 0.5693 (13) | 0.421 (7) | 0.036 (13) | |
H5A | 0.253846 | 0.678215 | 0.392906 | 0.043* | |
H5B | 0.253973 | 0.508661 | 0.321577 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.033 (6) | 0.030 (5) | 0.08 (5) | 0.010 (5) | −0.018 (17) | 0.010 (16) |
O2 | 0.040 (5) | 0.025 (4) | 0.06 (4) | −0.006 (4) | 0.003 (15) | −0.007 (13) |
O3 | 0.044 (7) | 0.017 (5) | 0.08 (7) | 0.000 (4) | −0.01 (2) | 0.012 (17) |
O1 | 0.027 (6) | 0.030 (5) | 0.03 (4) | 0.001 (4) | 0.010 (14) | 0.006 (16) |
O5 | 0.036 (5) | 0.028 (4) | 0.04 (3) | −0.004 (4) | 0.023 (14) | −0.015 (15) |
C3 | 0.037 (7) | 0.028 (6) | 0.09 (5) | 0.001 (6) | 0.002 (15) | 0.027 (16) |
C2 | 0.032 (6) | 0.021 (5) | 0.036 (19) | 0.008 (5) | 0.000 (11) | −0.009 (11) |
C1 | 0.039 (8) | 0.024 (5) | 0.037 (19) | 0.004 (5) | 0.000 (12) | −0.002 (11) |
C4 | 0.036 (7) | 0.020 (5) | 0.08 (5) | 0.006 (6) | 0.008 (14) | 0.004 (15) |
C5 | 0.030 (7) | 0.028 (7) | 0.05 (4) | −0.013 (6) | 0.019 (15) | −0.007 (18) |
Geometric parameters (Å, º) top
O4—C4 | 1.38 (5) | C3—C2 | 1.49 (2) |
O2—C2 | 1.40 (5) | C3—C4 | 1.51 (3) |
O3—C3 | 1.44 (3) | C2—C1 | 1.492 (15) |
O1—C1 | 1.48 (3) | C4—C5 | 1.52 (2) |
O5—C5 | 1.34 (5) | | |
| | | |
O3—C3—C2 | 109.5 (15) | O1—C1—C2 | 110.1 (14) |
O3—C3—C4 | 109 (2) | O4—C4—C3 | 108.5 (18) |
C2—C3—C4 | 117 (4) | O4—C4—C5 | 110 (2) |
O2—C2—C3 | 115 (5) | C3—C4—C5 | 110 (3) |
O2—C2—C1 | 107 (3) | O5—C5—C4 | 110 (4) |
C3—C2—C1 | 108.8 (11) | | |