Download citation
Download citation
link to html
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

cif

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

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol0_0001GPasup2.hkl
Contains datablock Xylitol0_0001GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol0_33GPasup3.hkl
Contains datablock Xylitol0_33GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol0_63GPasup4.hkl
Contains datablock Xylitol0_63GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol0_8GPasup5.hkl
Contains datablock Xylitol0_8GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol0_96GPasup6.hkl
Contains datablock Xylitol0_96GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol1_60GPasup7.hkl
Contains datablock Xylitol1_60GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol2GPasup8.hkl
Contains datablock Xylitol2GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol2_60GPasup9.hkl
Contains datablock Xylitol2_60GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol3_20GPasup10.hkl
Contains datablock Xylitol3_20GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol3_90GPasup11.hkl
Contains datablock Xylitol3_90GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621000445/um5047Xylitol4_70GPasup12.hkl
Contains datablock Xylitol4_70GPa

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520621000445/um5047Xylitol4_70GPasup13.cml
Supplementary material

pdf

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

Computing details top

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).

(Xylitol0_0001GPa) top
Crystal data top
C5H12O5Dx = 1.514 Mg m3
Mr = 152.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 632 reflections
a = 8.2993 (3) Åθ = 4.9–26.3°
b = 8.9697 (4) ŵ = 0.14 mm1
c = 8.9693 (4) ÅT = 286 K
V = 667.69 (5) Å3Prism
Z = 40.4 × 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 Source937 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
Detector resolution: 16.2413 pixels mm-1θmax = 26.9°, θmin = 3.2°
ω scansh = 103
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 = 511
Tmin = 0.986, Tmax = 1.000l = 511
1283 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.06Δρmax = 0.15 e Å3
1011 reflectionsΔρmin = 0.19 e Å3
96 parametersAbsolute structure: Flack x determined using 233 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
0 restraintsAbsolute 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
xyzUiso*/Ueq
O40.4795 (2)0.6418 (2)0.61780 (18)0.0280 (4)
H40.5143870.5960110.6900470.042*
O20.8644 (2)0.5668 (2)0.3147 (2)0.0296 (5)
H20.8975700.6513490.3311630.044*
O30.5694 (2)0.7090 (2)0.32032 (19)0.0283 (4)
H30.5779650.7085100.2292460.042*
O10.9278 (2)0.3289 (2)0.5217 (2)0.0301 (5)
H10.9881500.4001480.5091940.045*
O50.1631 (2)0.5337 (2)0.5436 (2)0.0327 (5)
H50.1372660.6111940.5857710.049*
C30.5776 (3)0.5587 (3)0.3754 (3)0.0230 (5)
H3A0.5513750.4907470.2933460.028*
C20.7508 (3)0.5253 (3)0.4276 (3)0.0218 (5)
H2A0.7733690.5811040.5192410.026*
C10.7742 (3)0.3604 (3)0.4558 (3)0.0267 (6)
H1A0.6896120.3249890.5215090.032*
H1B0.7650490.3069390.3621970.032*
C40.4518 (3)0.5394 (3)0.4966 (3)0.0232 (6)
H4A0.4585250.4373290.5351140.028*
C50.2835 (3)0.5647 (4)0.4349 (3)0.0292 (6)
H5A0.2733660.6674660.4024280.035*
H5B0.2670200.5010300.3488500.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0318 (9)0.0276 (11)0.0247 (8)0.0045 (8)0.0049 (8)0.0031 (8)
O20.0265 (9)0.0273 (11)0.0351 (10)0.0019 (8)0.0082 (8)0.0009 (9)
O30.0336 (9)0.0211 (11)0.0303 (9)0.0011 (8)0.0012 (9)0.0025 (8)
O10.0221 (8)0.0240 (11)0.0442 (10)0.0014 (8)0.0024 (9)0.0020 (9)
O50.0227 (9)0.0292 (12)0.0463 (11)0.0022 (9)0.0058 (9)0.0066 (9)
C30.0236 (11)0.0170 (13)0.0284 (12)0.0004 (11)0.0011 (11)0.0037 (11)
C20.0205 (11)0.0200 (14)0.0247 (11)0.0005 (11)0.0033 (10)0.0016 (11)
C10.0200 (11)0.0218 (15)0.0383 (15)0.0003 (11)0.0011 (11)0.0025 (13)
C40.0227 (12)0.0182 (14)0.0287 (13)0.0016 (10)0.0017 (11)0.0036 (11)
C50.0234 (12)0.0324 (17)0.0316 (13)0.0004 (11)0.0011 (11)0.0054 (13)
Geometric parameters (Å, º) top
O4—C41.441 (3)C3—C21.541 (3)
O2—C21.433 (3)C3—C41.517 (3)
O3—C31.437 (3)C2—C11.513 (4)
O1—C11.433 (3)C4—C51.520 (3)
O5—C51.424 (3)
O3—C3—C2109.3 (2)O1—C1—C2112.1 (2)
O3—C3—C4108.71 (19)O4—C4—C3111.0 (2)
C4—C3—C2113.69 (19)O4—C4—C5109.0 (2)
O2—C2—C3110.40 (19)C3—C4—C5110.76 (19)
O2—C2—C1106.7 (2)O5—C5—C4111.5 (2)
C1—C2—C3111.1 (2)
(Xylitol0_33GPa) top
Crystal data top
C5H12O5Dx = 1.546 Mg m3
Mr = 152.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 1465 reflections
a = 8.2694 (3) Åθ = 4.1–25.9°
b = 8.9403 (12) ŵ = 0.14 mm1
c = 8.8438 (9) ÅT = 296 K
V = 653.83 (11) Å3Prism
Z = 40.15 × 0.11 × 0.1 mm
F(000) = 328
Data collection top
Xcalibur, Eos
diffractometer
θmax = 26.8°, θmin = 4.1°
2431 measured reflectionsh = 910
547 independent reflectionsk = 77
504 reflections with I > 2σ(I)l = 88
Rint = 0.020
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.12Δρmax = 0.11 e Å3
547 reflectionsΔρmin = 0.10 e Å3
94 parametersAbsolute structure: Flack x determined using 194 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
0 restraintsAbsolute 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
xyzUiso*/Ueq
O40.4768 (3)0.6426 (4)0.6173 (4)0.0280 (9)
H40.5046210.5966580.6932520.042*
O20.8629 (2)0.5686 (3)0.3104 (3)0.0292 (9)
H20.9072080.6468580.3353620.044*
O30.5666 (3)0.7109 (4)0.3165 (3)0.0286 (10)
H30.5728460.7102430.2239810.043*
O10.9266 (3)0.3265 (4)0.5152 (3)0.0290 (9)
H10.9858120.3998420.5084820.044*
O50.1595 (3)0.5328 (4)0.5423 (3)0.0320 (9)
H50.1348570.6102150.5863390.048*
C30.5756 (3)0.5601 (6)0.3723 (5)0.0237 (12)
H3A0.5494410.4923660.2887130.028*
C20.7489 (4)0.5250 (6)0.4254 (5)0.0212 (11)
H2A0.7717070.5797820.5189140.025*
C10.7721 (4)0.3609 (6)0.4515 (5)0.0285 (14)
H1A0.6881720.3251240.5190730.034*
H1B0.7605820.3084590.3561240.034*
C40.4492 (3)0.5383 (7)0.4952 (5)0.0224 (12)
H4A0.4565930.4359680.5342910.027*
C50.2805 (3)0.5642 (6)0.4317 (5)0.0278 (12)
H5A0.2705130.6673570.3989180.033*
H5B0.2640910.5003990.3442980.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0318 (12)0.027 (5)0.026 (4)0.0047 (13)0.0059 (11)0.0034 (12)
O20.0241 (10)0.032 (4)0.032 (3)0.0061 (12)0.0086 (11)0.0023 (11)
O30.0325 (12)0.030 (4)0.024 (3)0.0015 (13)0.0030 (13)0.0024 (13)
O10.0223 (11)0.021 (4)0.044 (3)0.0035 (12)0.0023 (12)0.0014 (12)
O50.0226 (11)0.034 (4)0.039 (3)0.0038 (14)0.0055 (12)0.0057 (13)
C30.0217 (15)0.015 (6)0.034 (4)0.0011 (17)0.0008 (15)0.0025 (18)
C20.0208 (13)0.020 (5)0.022 (4)0.0014 (18)0.0028 (14)0.0007 (16)
C10.0204 (15)0.028 (7)0.037 (5)0.0015 (19)0.0021 (16)0.0007 (18)
C40.0210 (14)0.021 (6)0.026 (4)0.0015 (18)0.0008 (16)0.0053 (18)
C50.0220 (15)0.033 (6)0.028 (4)0.0021 (18)0.0017 (15)0.0026 (18)
Geometric parameters (Å, º) top
O4—C41.445 (5)C3—C21.540 (4)
O2—C21.441 (4)C3—C41.520 (6)
O3—C31.437 (5)C2—C11.497 (7)
O1—C11.430 (4)C4—C51.522 (4)
O5—C51.427 (4)
O3—C3—C2110.1 (3)O1—C1—C2112.7 (3)
O3—C3—C4109.3 (4)O4—C4—C3110.1 (4)
C4—C3—C2113.3 (3)O4—C4—C5108.8 (3)
O2—C2—C3109.8 (3)C3—C4—C5110.3 (4)
O2—C2—C1106.9 (3)O5—C5—C4111.1 (4)
C1—C2—C3111.5 (4)
(Xylitol0_63GPa) top
Crystal data top
C5H12O5F(000) = 328
Mr = 152.15Dx = 1.575 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 8.2305 (2) ÅCell parameters from 1323 reflections
b = 8.8992 (11) Åθ = 4.1–25.9°
c = 8.7624 (8) ŵ = 0.14 mm1
V = 641.80 (10) Å3T = 296 K
Z = 4Prism
Data collection top
Multiwire proportional
diffractometer
Rint = 0.020
Graphite monochromatorθmax = 26.2°, θmin = 4.1°
phi and ω scansh = 1010
2149 measured reflectionsk = 77
482 independent reflectionsl = 88
456 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.13Δρmax = 0.10 e Å3
482 reflectionsΔρmin = 0.11 e Å3
96 parametersAbsolute structure: Flack x determined using 176 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
0 restraintsAbsolute 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
xyzUiso*/Ueq
O40.4754 (3)0.6430 (5)0.6178 (4)0.0253 (10)
H40.5087160.5977330.6929990.038*
O20.8625 (3)0.5690 (4)0.3075 (4)0.0272 (10)
H20.8938840.6548370.3243890.041*
O30.5652 (3)0.7119 (4)0.3146 (3)0.0266 (10)
H30.5767580.7118970.2216250.040*
O10.9268 (3)0.3255 (4)0.5111 (3)0.0274 (9)
H10.9868170.3985270.5024930.041*
O50.1578 (3)0.5321 (4)0.5417 (4)0.0294 (9)
H50.1275800.6104170.5819310.044*
C30.5744 (3)0.5614 (5)0.3703 (5)0.0220 (13)
H3A0.5479550.4938320.2855840.026*
C20.7483 (4)0.5250 (7)0.4231 (5)0.0200 (11)
H2A0.7716680.5795760.5177600.024*
C10.7708 (4)0.3606 (6)0.4489 (6)0.0266 (14)
H1A0.6872850.3249350.5181470.032*
H1B0.7576090.3080180.3527500.032*
C40.4481 (4)0.5376 (7)0.4945 (6)0.0218 (14)
H4A0.4558730.4346470.5334470.026*
C50.2788 (3)0.5646 (6)0.4307 (5)0.0255 (13)
H5A0.2689680.6685800.3988460.031*
H5B0.2621910.5014790.3418020.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0286 (12)0.019 (5)0.029 (4)0.0046 (13)0.0061 (11)0.0036 (13)
O20.0233 (11)0.023 (5)0.035 (3)0.0047 (13)0.0078 (11)0.0010 (11)
O30.0300 (11)0.028 (5)0.022 (3)0.0033 (14)0.0034 (13)0.0032 (12)
O10.0209 (10)0.020 (5)0.041 (4)0.0020 (13)0.0034 (12)0.0011 (11)
O50.0208 (12)0.029 (4)0.038 (3)0.0023 (15)0.0060 (12)0.0055 (13)
C30.0194 (15)0.016 (6)0.030 (5)0.0008 (19)0.0009 (15)0.0028 (18)
C20.0179 (13)0.027 (6)0.015 (4)0.001 (2)0.0029 (14)0.0007 (16)
C10.0190 (15)0.034 (7)0.027 (5)0.000 (2)0.0010 (16)0.0019 (17)
C40.0211 (15)0.024 (7)0.020 (5)0.001 (2)0.0014 (17)0.0050 (18)
C50.0198 (15)0.028 (7)0.029 (5)0.0012 (19)0.0009 (14)0.0031 (17)
Geometric parameters (Å, º) top
O4—C41.448 (6)C3—C21.539 (5)
O2—C21.436 (4)C3—C41.519 (6)
O3—C31.428 (5)C2—C11.493 (8)
O1—C11.429 (4)C4—C51.521 (5)
O5—C51.422 (5)
O3—C3—C2110.5 (3)O1—C1—C2112.6 (3)
O3—C3—C4109.8 (4)O4—C4—C3109.7 (4)
C4—C3—C2113.0 (4)O4—C4—C5108.3 (4)
O2—C2—C3109.8 (3)C3—C4—C5110.0 (4)
O2—C2—C1107.0 (4)O5—C5—C4111.0 (4)
C1—C2—C3111.6 (4)
(Xylitol0_8GPa) top
Crystal data top
C5H12O5Dx = 1.586 Mg m3
Mr = 152.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 189 reflections
a = 8.2213 (4) Åθ = 5.5–24.8°
b = 8.883 (2) ŵ = 0.14 mm1
c = 8.7242 (17) ÅT = 296 K
V = 637.1 (2) Å3Prism
Z = 40.15 × 0.11 × 0.1 mm
F(000) = 328
Data collection top
Multiwire proportional
diffractometer
Rint = 0.007
Graphite monochromatorθmax = 26.0°, θmin = 5.5°
phi and ω scansh = 99
305 measured reflectionsk = 66
280 independent reflectionsl = 77
276 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.21Δρmax = 0.07 e Å3
280 reflectionsΔρmin = 0.07 e Å3
96 parametersAbsolute structure: Flack x determined using 115 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
20 restraintsAbsolute 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
xyzUiso*/Ueq
O40.4748 (7)0.6426 (12)0.6184 (9)0.028 (2)
H40.5104000.5977740.6933810.041*
O20.8625 (7)0.5696 (10)0.3065 (10)0.027 (2)
H20.8887440.6578460.3185820.040*
O30.5644 (8)0.7123 (11)0.3145 (8)0.026 (4)
H30.5735650.7129300.2209320.039*
O10.9269 (7)0.3250 (9)0.5083 (8)0.027 (2)
H10.9873040.3980970.5008800.041*
O50.1570 (7)0.5308 (10)0.5411 (9)0.027 (3)
H50.1251460.6092290.5806150.041*
C30.5736 (10)0.5601 (17)0.3694 (13)0.022 (4)
H3A0.5481180.4922520.2841270.026*
C20.7473 (10)0.5271 (17)0.4231 (12)0.020 (4)
H2A0.7700390.5818630.5182230.024*
C10.7705 (10)0.3620 (17)0.4476 (13)0.025 (4)
H1A0.6873890.3258880.5174270.030*
H1B0.7559760.3103020.3505920.030*
C40.4478 (8)0.5364 (16)0.4942 (14)0.019 (2)
H4A0.4552850.4332420.5334570.022*
C50.2777 (7)0.5642 (14)0.4298 (11)0.024 (4)
H5A0.2679690.6685770.3985540.028*
H5B0.2610960.5015320.3400580.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.029 (3)0.021 (12)0.033 (11)0.003 (3)0.005 (3)0.007 (4)
O20.026 (3)0.026 (4)0.029 (4)0.002 (3)0.008 (2)0.001 (3)
O30.032 (3)0.034 (18)0.012 (11)0.000 (4)0.001 (3)0.004 (4)
O10.020 (3)0.011 (13)0.051 (10)0.000 (3)0.003 (3)0.004 (4)
O50.021 (3)0.017 (13)0.043 (9)0.005 (4)0.007 (3)0.006 (3)
C30.018 (4)0.012 (14)0.036 (12)0.001 (5)0.002 (4)0.003 (6)
C20.022 (5)0.01 (2)0.023 (15)0.007 (6)0.009 (4)0.001 (4)
C10.015 (4)0.03 (2)0.030 (17)0.000 (5)0.002 (3)0.002 (6)
C40.018 (3)0.019 (3)0.019 (3)0.001 (2)0.0006 (19)0.000 (2)
C50.017 (4)0.03 (2)0.023 (15)0.002 (5)0.001 (3)0.003 (5)
Geometric parameters (Å, º) top
O4—C41.454 (13)C3—C21.531 (12)
O2—C21.440 (11)C3—C41.517 (15)
O3—C31.437 (13)C2—C11.494 (17)
O1—C11.429 (9)C4—C51.527 (11)
O5—C51.420 (10)
O3—C3—C2109.3 (10)O1—C1—C2113.2 (10)
O3—C3—C4109.5 (9)O4—C4—C3109.9 (10)
C4—C3—C2113.0 (8)O4—C4—C5108.0 (8)
O2—C2—C3110.3 (8)C3—C4—C5109.7 (10)
O2—C2—C1105.9 (9)O5—C5—C4110.8 (8)
C1—C2—C3110.5 (11)
(Xylitol0_96GPa) top
Crystal data top
C5H12O5Dx = 1.603 Mg m3
Mr = 152.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 805 reflections
a = 8.204 (2) Åθ = 3.3–20.3°
b = 8.854 (2) ŵ = 0.14 mm1
c = 8.6809 (7) ÅT = 296 K
V = 630.6 (2) Å3Prism
Z = 40.15 × 0.11 × 0.1 mm
F(000) = 328
Data collection top
Multiwire proportional
diffractometer
Rint = 0.065
Graphite monochromatorθmax = 27.3°, θmin = 3.3°
phi and ω scansh = 77
2619 measured reflectionsk = 88
467 independent reflectionsl = 1111
377 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.09Δρmax = 0.11 e Å3
467 reflectionsΔρmin = 0.13 e Å3
94 parametersAbsolute structure: Flack x determined using 141 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
7 restraintsAbsolute 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
xyzUiso*/Ueq
O40.4743 (7)0.6414 (7)0.6198 (4)0.0327 (16)
H40.5171130.5951870.6909410.049*
O20.8621 (7)0.5708 (5)0.3055 (4)0.0345 (15)
H20.9083980.6483020.3331410.052*
O30.5648 (8)0.7135 (6)0.3134 (4)0.0345 (14)
H30.5719890.7137610.2191570.052*
O10.9253 (9)0.3258 (7)0.5080 (4)0.0376 (17)
H10.9885190.3955490.4909100.056*
O50.1573 (8)0.5325 (7)0.5401 (5)0.0366 (17)
H50.1398620.6073490.5932210.055*
C30.5752 (11)0.5614 (9)0.3688 (6)0.028 (2)
H3A0.5488590.4938880.2828710.034*
C20.7473 (12)0.5268 (9)0.4195 (7)0.030 (2)
H2A0.7704150.5810890.5153730.035*
C10.7706 (12)0.3607 (10)0.4455 (8)0.032 (2)
H1A0.6866460.3246020.5150090.039*
H1B0.7577690.3080510.3482560.039*
C40.4455 (11)0.5393 (9)0.4927 (6)0.0286 (19)
H4A0.4517950.4352400.5307800.034*
C50.2780 (11)0.5662 (9)0.4297 (8)0.032 (2)
H5A0.2679590.6710740.3986250.038*
H5B0.2616080.5037420.3392150.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.015 (9)0.051 (7)0.0315 (17)0.004 (2)0.007 (2)0.003 (2)
O20.019 (8)0.044 (7)0.041 (2)0.003 (2)0.004 (3)0.002 (2)
O30.036 (8)0.030 (7)0.0377 (18)0.000 (2)0.004 (3)0.001 (2)
O10.010 (9)0.049 (8)0.053 (2)0.002 (2)0.007 (3)0.003 (3)
O50.008 (10)0.055 (8)0.046 (2)0.006 (2)0.007 (3)0.004 (3)
C30.008 (12)0.043 (10)0.032 (3)0.000 (3)0.004 (4)0.002 (4)
C20.016 (9)0.044 (9)0.029 (3)0.001 (4)0.000 (4)0.007 (3)
C10.027 (13)0.031 (10)0.038 (3)0.003 (4)0.002 (4)0.003 (4)
C40.027 (12)0.026 (9)0.033 (3)0.001 (3)0.001 (4)0.001 (3)
C50.032 (12)0.027 (10)0.036 (3)0.001 (3)0.007 (4)0.004 (3)
Geometric parameters (Å, º) top
O4—C41.446 (8)C3—C21.510 (10)
O2—C21.420 (10)C3—C41.526 (10)
O3—C31.433 (8)C2—C11.500 (11)
O1—C11.415 (9)C4—C51.498 (10)
O5—C51.410 (8)
O3—C3—C2110.2 (6)O1—C1—C2112.7 (7)
O3—C3—C4108.4 (5)O4—C4—C3110.1 (6)
C2—C3—C4114.9 (6)O4—C4—C5109.2 (6)
O2—C2—C3111.2 (5)C5—C4—C3111.2 (5)
O2—C2—C1106.8 (6)O5—C5—C4111.2 (5)
C1—C2—C3111.2 (7)
(Xylitol1_60GPa) top
Crystal data top
C5H12O5Dx = 1.646 Mg m3
Mr = 152.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 1044 reflections
a = 8.1540 (5) Åθ = 3.3–20.5°
b = 8.7964 (16) ŵ = 0.15 mm1
c = 8.5610 (19) ÅT = 296 K
V = 614.04 (18) Å3Prism
Z = 40.15 × 0.11 × 0.1 mm
F(000) = 328
Data collection top
Multiwire proportional
diffractometer
Rint = 0.059
Graphite monochromatorθmax = 27.0°, θmin = 3.3°
phi and ω scansh = 1010
2583 measured reflectionsk = 88
502 independent reflectionsl = 77
405 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.09Δρmax = 0.11 e Å3
502 reflectionsΔρmin = 0.10 e Å3
96 parametersAbsolute structure: Flack x determined using 139 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
14 restraintsAbsolute 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
xyzUiso*/Ueq
O40.4724 (4)0.6423 (7)0.6195 (7)0.0257 (14)
H40.5185430.5964910.6904680.039*
O20.8614 (4)0.5715 (5)0.3015 (5)0.0269 (14)
H20.9016890.6539110.3248360.040*
O30.5638 (6)0.7170 (5)0.3097 (6)0.0264 (15)
H30.5603090.7176330.2139700.040*
O10.9274 (4)0.3227 (5)0.5013 (6)0.0275 (14)
H10.9839010.3997330.5047940.041*
O50.1533 (4)0.5309 (5)0.5393 (6)0.0288 (14)
H50.1268780.6090020.5851070.043*
C30.5729 (6)0.5629 (8)0.3641 (8)0.0215 (18)
H3A0.5467040.4953530.2765910.026*
C20.7458 (6)0.5275 (8)0.4184 (8)0.0180 (17)
H2A0.7687200.5818280.5159580.022*
C10.7682 (5)0.3600 (9)0.4425 (8)0.025 (2)
H1A0.6858520.3237540.5152430.030*
H1B0.7513660.3079970.3438370.030*
C40.4440 (6)0.5399 (9)0.4907 (11)0.0200 (19)
H4A0.4514880.4351290.5290720.024*
C50.2743 (5)0.5651 (8)0.4254 (8)0.027 (2)
H5A0.2629840.6702080.3927020.032*
H5B0.2583260.5009620.3344930.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.028 (2)0.028 (8)0.021 (8)0.005 (2)0.010 (3)0.002 (2)
O20.025 (2)0.025 (6)0.031 (7)0.004 (2)0.004 (2)0.0022 (19)
O30.031 (2)0.023 (6)0.026 (7)0.002 (2)0.006 (3)0.001 (2)
O10.024 (2)0.021 (6)0.037 (7)0.000 (2)0.007 (2)0.001 (2)
O50.0212 (18)0.032 (5)0.033 (6)0.002 (2)0.007 (2)0.006 (2)
C30.023 (3)0.015 (7)0.027 (8)0.002 (3)0.003 (3)0.001 (3)
C20.015 (2)0.014 (8)0.025 (10)0.000 (3)0.005 (3)0.001 (3)
C10.014 (3)0.027 (9)0.035 (11)0.001 (3)0.000 (3)0.005 (3)
C40.019 (3)0.015 (8)0.026 (9)0.001 (3)0.006 (3)0.001 (4)
C50.020 (3)0.012 (9)0.048 (11)0.002 (3)0.001 (3)0.008 (3)
Geometric parameters (Å, º) top
O4—C41.443 (9)C3—C21.516 (6)
O2—C21.428 (7)C3—C41.523 (10)
O3—C31.435 (6)C2—C11.499 (9)
O1—C11.430 (6)C4—C51.509 (7)
O5—C51.420 (7)
O3—C3—C2109.9 (5)O1—C1—C2112.6 (5)
O3—C3—C4108.7 (5)O4—C4—C3110.5 (6)
C2—C3—C4113.4 (5)O4—C4—C5109.8 (6)
O2—C2—C3110.1 (5)C5—C4—C3110.5 (7)
O2—C2—C1106.4 (5)O5—C5—C4110.6 (6)
C1—C2—C3110.9 (5)
(Xylitol2GPa) top
Crystal data top
C5H12O5Dx = 1.684 Mg m3
Mr = 152.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 402 reflections
a = 8.105 (9) Åθ = 3.4–18.4°
b = 8.752 (6) ŵ = 0.15 mm1
c = 8.462 (2) ÅT = 296 K
V = 600.3 (8) Å3Prism
Z = 40.15 × 0.11 × 0.1 mm
F(000) = 328
Data collection top
Multiwire proportional
diffractometer
Rint = 0.120
Graphite monochromatorθmax = 26.8°, θmin = 3.4°
phi and ω scansh = 77
2462 measured reflectionsk = 88
391 independent reflectionsl = 1010
256 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.04Δρmax = 0.18 e Å3
391 reflectionsΔρmin = 0.15 e Å3
95 parametersAbsolute structure: Flack x determined using 84 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
60 restraintsAbsolute 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
xyzUiso*/Ueq
O40.4713 (17)0.6411 (15)0.6202 (9)0.049 (4)
H40.5086170.5912390.6940480.073*
O20.8612 (19)0.5724 (16)0.2970 (12)0.048 (4)
H20.9122720.6481480.3265370.072*
O30.5648 (18)0.7185 (14)0.3064 (10)0.049 (3)
H30.5715880.7184920.2096720.073*
O10.9293 (19)0.3221 (14)0.4947 (11)0.050 (4)
H10.9888730.3977760.4927950.075*
O50.1512 (18)0.5312 (17)0.5375 (12)0.055 (4)
H50.1482260.5987210.6046140.082*
C30.575 (3)0.566 (2)0.3631 (16)0.042 (4)
H3A0.5489920.4984910.2745010.051*
C20.747 (3)0.529 (2)0.4148 (19)0.047 (4)
H2A0.7716580.5837470.5129990.057*
C10.767 (3)0.363 (2)0.441 (2)0.048 (5)
H1A0.6861580.3290150.5180420.057*
H1B0.7440300.3093760.3424590.057*
C40.443 (3)0.543 (2)0.4882 (13)0.043 (4)
H4A0.4498230.4367750.5251730.052*
C50.274 (3)0.568 (2)0.4211 (17)0.045 (5)
H5A0.2617850.6739260.3892590.054*
H5B0.2583920.5043010.3285020.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.015 (18)0.080 (14)0.052 (4)0.002 (6)0.013 (7)0.001 (6)
O20.024 (14)0.062 (14)0.059 (6)0.000 (5)0.008 (7)0.002 (6)
O30.023 (15)0.069 (13)0.053 (5)0.002 (5)0.005 (7)0.004 (5)
O10.010 (18)0.061 (16)0.079 (6)0.011 (6)0.012 (9)0.007 (7)
O50.012 (16)0.086 (16)0.066 (5)0.005 (6)0.005 (7)0.006 (6)
C30.016 (13)0.070 (12)0.042 (6)0.004 (7)0.001 (9)0.001 (8)
C20.012 (13)0.067 (13)0.063 (9)0.004 (8)0.002 (9)0.008 (8)
C10.009 (19)0.062 (13)0.072 (11)0.008 (8)0.002 (10)0.005 (9)
C40.010 (13)0.076 (16)0.044 (7)0.003 (7)0.006 (7)0.000 (7)
C50.012 (14)0.088 (18)0.036 (8)0.007 (8)0.005 (7)0.001 (7)
Geometric parameters (Å, º) top
O4—C41.430 (17)C3—C21.49 (2)
O2—C21.41 (2)C3—C41.52 (2)
O3—C31.419 (18)C2—C11.48 (3)
O1—C11.44 (2)C4—C51.50 (2)
O5—C51.435 (18)
O3—C3—C2111.1 (15)O1—C1—C2112.8 (16)
O3—C3—C4108.7 (13)O4—C4—C3110.4 (15)
C2—C3—C4115.1 (13)O4—C4—C5110.6 (15)
O2—C2—C3110.2 (15)C5—C4—C3111.2 (11)
O2—C2—C1107.3 (15)O5—C5—C4109.9 (12)
C1—C2—C3111.0 (15)
(Xylitol2_60GPa) top
Crystal data top
C5H12O5Dx = 1.722 Mg m3
Mr = 152.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 594 reflections
a = 8.0845 (8) Åθ = 3.5–23.5°
b = 8.67 (2) ŵ = 0.16 mm1
c = 8.3725 (11) ÅT = 296 K
V = 586.9 (14) Å3Prism
Z = 40.15 × 0.11 × 0.1 mm
F(000) = 328
Data collection top
Multiwire proportional
diffractometer
Rint = 0.073
Graphite monochromatorθmax = 27.5°, θmin = 3.5°
phi and ω scansh = 1010
2371 measured reflectionsk = 22
283 independent reflectionsl = 1010
192 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.22Δρmax = 0.10 e Å3
283 reflectionsΔρmin = 0.13 e Å3
94 parametersAbsolute structure: Flack x determined using 46 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
80 restraintsAbsolute 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
xyzUiso*/Ueq
O40.4704 (7)0.644 (4)0.6195 (7)0.04 (2)
H40.5031600.5919970.6951340.058*
O20.8653 (12)0.576 (3)0.2970 (11)0.061 (14)
H20.8621610.6697460.2829660.091*
O30.5607 (16)0.725 (3)0.3053 (10)0.055 (13)
H30.5711860.7277810.2079380.082*
O10.9291 (8)0.317 (5)0.4915 (8)0.049 (17)
H10.9876820.3937210.4950270.074*
O50.1508 (6)0.524 (4)0.5380 (7)0.032 (12)
H50.1090210.6010640.5772960.048*
C30.573 (2)0.571 (4)0.3578 (16)0.043 (13)
H3A0.5463300.5028500.2681940.052*
C20.7467 (19)0.534 (5)0.417 (2)0.038 (8)
H2A0.7698940.5864250.5177540.046*
C10.7667 (19)0.358 (5)0.435 (2)0.039 (8)
H1A0.6842990.3200770.5091570.047*
H1B0.7473200.3092640.3323400.047*
C40.4432 (12)0.548 (8)0.4884 (11)0.036 (17)
H4A0.4524710.4409840.5255850.043*
C50.2713 (8)0.568 (6)0.4201 (11)0.031 (7)
H5A0.2544720.6752430.3901630.038*
H5B0.2587910.5051640.3252290.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.035 (3)0.05 (6)0.031 (3)0.007 (12)0.004 (3)0.004 (9)
O20.032 (3)0.11 (4)0.045 (4)0.006 (13)0.012 (3)0.030 (13)
O30.039 (4)0.09 (4)0.039 (5)0.009 (15)0.003 (4)0.019 (14)
O10.027 (3)0.06 (5)0.056 (4)0.008 (15)0.004 (3)0.013 (15)
O50.025 (2)0.02 (4)0.051 (3)0.009 (12)0.007 (3)0.003 (11)
C30.026 (5)0.07 (4)0.036 (8)0.008 (14)0.005 (5)0.009 (16)
C20.025 (6)0.05 (2)0.037 (8)0.004 (15)0.010 (5)0.006 (19)
C10.024 (6)0.048 (19)0.045 (8)0.001 (12)0.005 (5)0.001 (14)
C40.025 (5)0.05 (5)0.037 (5)0.018 (16)0.005 (4)0.011 (14)
C50.024 (3)0.04 (2)0.034 (6)0.002 (10)0.003 (3)0.004 (11)
Geometric parameters (Å, º) top
O4—C41.39 (5)C3—C21.53 (3)
O2—C21.43 (2)C3—C41.53 (2)
O3—C31.41 (3)C2—C11.54 (3)
O1—C11.442 (19)C4—C51.513 (16)
O5—C51.440 (17)
O3—C3—C2111 (2)O1—C1—C2112 (2)
O3—C3—C4108 (3)O4—C4—C3112 (3)
C2—C3—C4111.9 (14)O4—C4—C5112 (3)
O2—C2—C3109.6 (18)C5—C4—C3110.1 (13)
O2—C2—C1105 (3)O5—C5—C4109.3 (14)
C3—C2—C1110 (2)
(Xylitol3_20GPa) top
Crystal data top
C5H12O5Dx = 1.742 Mg m3
Mr = 152.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 594 reflections
a = 8.0696 (15) Åθ = 3.5–23.5°
b = 8.65 (5) ŵ = 0.16 mm1
c = 8.309 (2) ÅT = 296 K
V = 580 (3) Å3Prism
Z = 40.15 × 0.11 × 0.1 mm
F(000) = 328
Data collection top
Multiwire proportional
diffractometer
Rint = 0.088
Graphite monochromatorθmax = 26.9°, θmin = 4.9°
phi and ω scansh = 910
2078 measured reflectionsk = 22
265 independent reflectionsl = 1010
175 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.16Δρmax = 0.14 e Å3
265 reflectionsΔρmin = 0.11 e Å3
93 parametersAbsolute structure: Flack x determined using 41 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
73 restraintsAbsolute 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
xyzUiso*/Ueq
O40.4731 (11)0.643 (5)0.6186 (9)0.08 (3)
H40.4631770.5987060.6883180.096*
O20.8636 (9)0.576 (4)0.2918 (9)0.04 (2)
H20.9195020.6469800.3286400.066*
O30.5616 (18)0.719 (5)0.3024 (14)0.054 (18)
H30.5683170.7181830.2184370.081*
O10.9299 (11)0.309 (6)0.4872 (16)0.046 (13)
H10.9849120.3864100.4896910.070*
O50.1495 (10)0.531 (5)0.5363 (9)0.07 (4)
H50.1133040.6152960.5651360.112*
C30.572 (3)0.570 (12)0.360 (2)0.053 (17)
H3A0.5420080.5011590.2706320.064*
C20.747 (3)0.521 (7)0.415 (3)0.044 (16)
H2A0.7724470.5717120.5177590.053*
C10.770 (3)0.346 (7)0.434 (4)0.058 (16)
H1A0.6893300.3065870.5104970.070*
H1B0.7496820.2956830.3312940.070*
C40.4425 (16)0.552 (10)0.4843 (16)0.05 (2)
H4A0.4574720.4462340.5235150.060*
C50.2716 (13)0.553 (8)0.4200 (14)0.037 (8)
H5A0.2521640.6513320.3668280.045*
H5B0.2617560.4724580.3395940.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.052 (5)0.15 (8)0.041 (4)0.007 (17)0.005 (4)0.013 (12)
O20.042 (4)0.04 (6)0.047 (4)0.015 (18)0.006 (5)0.033 (15)
O30.040 (5)0.08 (6)0.045 (7)0.000 (17)0.006 (7)0.024 (18)
O10.035 (5)0.04 (4)0.063 (6)0.003 (16)0.007 (5)0.011 (17)
O50.033 (4)0.13 (12)0.057 (5)0.04 (2)0.005 (5)0.007 (17)
C30.043 (7)0.08 (5)0.033 (10)0.012 (17)0.006 (7)0.026 (18)
C20.029 (8)0.07 (5)0.037 (11)0.013 (17)0.005 (7)0.00 (2)
C10.036 (8)0.07 (5)0.069 (13)0.009 (19)0.007 (8)0.01 (3)
C40.036 (6)0.07 (7)0.042 (7)0.007 (19)0.001 (6)0.023 (18)
C50.037 (5)0.04 (2)0.033 (8)0.003 (12)0.001 (5)0.003 (14)
Geometric parameters (Å, º) top
O4—C41.39 (6)C3—C21.54 (4)
O2—C21.47 (4)C3—C41.48 (3)
O3—C31.38 (11)C2—C11.54 (3)
O1—C11.40 (3)C4—C51.478 (18)
O5—C51.393 (16)
O3—C3—C2115 (5)O1—C1—C2111 (4)
O3—C3—C4107 (5)O4—C4—C3112 (4)
C4—C3—C2114 (2)O4—C4—C5117 (4)
O2—C2—C3107 (3)C5—C4—C3114.0 (14)
O2—C2—C1108 (4)O5—C5—C4114.1 (12)
C1—C2—C3114 (4)
(Xylitol3_90GPa) top
Crystal data top
C5H12O5Dx = 1.770 Mg m3
Mr = 152.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 739 reflections
a = 8.0108 (4) Åθ = 4.7–24.2°
b = 8.6270 (5) ŵ = 0.16 mm1
c = 8.263 (8) ÅT = 293 K
V = 571.0 (6) Å3Prism
Z = 40.15 × 0.11 × 0.1 mm
F(000) = 328
Data collection top
Xcalibur, Eos
diffractometer
θmax = 27.0°, θmin = 4.7°
2081 measured reflectionsh = 109
303 independent reflectionsk = 1010
238 reflections with I > 2σ(I)l = 22
Rint = 0.048
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.06Δρmax = 0.07 e Å3
303 reflectionsΔρmin = 0.08 e Å3
96 parametersAbsolute structure: Flack x determined using 64 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
60 restraintsAbsolute 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
xyzUiso*/Ueq
O41.4694 (5)1.6442 (6)1.622 (2)0.026 (6)
H41.5100311.5942041.6962220.040*
O21.8656 (5)1.5748 (3)1.2890 (17)0.020 (8)
H21.8990501.6626671.3086650.030*
O31.5634 (10)1.7261 (5)1.300 (3)0.023 (11)
H31.5430841.7276181.2027800.034*
O11.9301 (5)1.3162 (5)1.485 (3)0.044 (18)
H11.9917411.3916841.4770230.067*
O51.1483 (5)1.5291 (4)1.5362 (17)0.034 (10)
H51.1285901.6050501.5926900.051*
C31.5718 (6)1.5685 (6)1.355 (4)0.023 (8)
H3A1.5444011.5016751.2626960.028*
C21.7475 (6)1.5307 (6)1.406 (3)0.021 (9)
H2A1.7723081.5833061.5087200.025*
C11.7650 (5)1.3565 (6)1.429 (2)0.029 (13)
H1A1.6828141.3208141.5066690.035*
H1B1.7434341.3047241.3268140.035*
C41.4412 (7)1.5422 (7)1.483 (3)0.025 (7)
H4A1.4491811.4345251.5200470.030*
C51.2688 (6)1.5686 (6)1.417 (3)0.032 (8)
H5A1.2558731.6765461.3871290.038*
H5B1.2520931.5056141.3215490.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.022 (3)0.026 (3)0.03 (2)0.0050 (19)0.001 (6)0.006 (8)
O20.0228 (17)0.0167 (19)0.02 (2)0.0019 (15)0.003 (6)0.000 (6)
O30.027 (3)0.015 (2)0.03 (3)0.0012 (16)0.002 (8)0.006 (6)
O10.011 (2)0.017 (2)0.10 (6)0.0035 (15)0.001 (7)0.002 (7)
O50.0192 (19)0.0206 (19)0.06 (3)0.0030 (15)0.005 (6)0.008 (5)
C30.019 (3)0.016 (3)0.04 (2)0.001 (2)0.006 (8)0.000 (7)
C20.012 (2)0.020 (3)0.03 (3)0.002 (2)0.002 (7)0.008 (7)
C10.012 (3)0.021 (3)0.05 (4)0.0020 (19)0.008 (7)0.001 (7)
C40.023 (3)0.013 (3)0.04 (2)0.003 (2)0.006 (8)0.004 (7)
C50.011 (3)0.023 (3)0.06 (3)0.000 (2)0.000 (7)0.011 (8)
Geometric parameters (Å, º) top
O4—C41.46 (2)C3—C21.506 (14)
O2—C21.41 (2)C3—C41.51 (3)
O3—C31.435 (15)C2—C11.521 (8)
O1—C11.445 (10)C4—C51.501 (13)
O5—C51.418 (19)
O3—C3—C2109.8 (5)O1—C1—C2111.2 (5)
O3—C3—C4109.4 (11)O4—C4—C3110.6 (10)
C2—C3—C4115 (2)O4—C4—C5109.5 (10)
O2—C2—C3112.0 (18)C5—C4—C3111.2 (18)
O2—C2—C1106.8 (10)O5—C5—C4109.9 (16)
C3—C2—C1109.6 (5)
(Xylitol4_70GPa) top
Crystal data top
C5H12O5Dx = 1.798 Mg m3
Mr = 152.15Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 396 reflections
a = 7.9846 (14) Åθ = 3.4–23.6°
b = 8.6043 (11) ŵ = 0.16 mm1
c = 8.179 (12) ÅT = 296 K
V = 561.9 (9) Å3Prism
Z = 40.15 × 0.11 × 0.1 mm
F(000) = 328
Data collection top
Multiwire proportional
diffractometer
Rint = 0.210
Graphite monochromatorθmax = 27.7°, θmin = 3.5°
phi and ω scansh = 1010
2216 measured reflectionsk = 1010
290 independent reflectionsl = 22
160 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.01Δρmax = 0.13 e Å3
290 reflectionsΔρmin = 0.13 e Å3
95 parametersAbsolute structure: Flack x determined using 34 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
86 restraintsAbsolute 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
xyzUiso*/Ueq
O40.4714 (16)0.6451 (10)0.618 (5)0.049 (16)
H40.4900140.5960540.7018820.074*
O20.8672 (12)0.5756 (7)0.288 (5)0.041 (12)
H20.8895230.6677630.3007820.062*
O30.564 (3)0.7269 (9)0.304 (6)0.05 (2)
H30.5759950.7287950.2043940.070*
O10.9315 (14)0.3162 (12)0.484 (6)0.028 (12)
H10.9937700.3916330.4768590.042*
O50.1509 (12)0.5276 (9)0.530 (4)0.035 (11)
H50.1294720.6016580.5898130.053*
C30.5724 (16)0.5682 (13)0.361 (6)0.050 (16)
H3A0.5417060.5019720.2680930.060*
C20.7488 (18)0.5293 (12)0.404 (8)0.030 (7)
H2A0.7762940.5776750.5087070.036*
C10.7641 (13)0.3572 (11)0.420 (6)0.033 (7)
H1A0.6917510.3249010.4829110.040*
H1B0.7500060.3159780.3311180.040*
C40.4413 (19)0.5428 (15)0.491 (6)0.047 (16)
H4A0.4494120.4359420.5315790.056*
C50.2675 (16)0.5693 (13)0.421 (7)0.036 (13)
H5A0.2538460.6782150.3929060.043*
H5B0.2539730.5086610.3215770.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.033 (6)0.030 (5)0.08 (5)0.010 (5)0.018 (17)0.010 (16)
O20.040 (5)0.025 (4)0.06 (4)0.006 (4)0.003 (15)0.007 (13)
O30.044 (7)0.017 (5)0.08 (7)0.000 (4)0.01 (2)0.012 (17)
O10.027 (6)0.030 (5)0.03 (4)0.001 (4)0.010 (14)0.006 (16)
O50.036 (5)0.028 (4)0.04 (3)0.004 (4)0.023 (14)0.015 (15)
C30.037 (7)0.028 (6)0.09 (5)0.001 (6)0.002 (15)0.027 (16)
C20.032 (6)0.021 (5)0.036 (19)0.008 (5)0.000 (11)0.009 (11)
C10.039 (8)0.024 (5)0.037 (19)0.004 (5)0.000 (12)0.002 (11)
C40.036 (7)0.020 (5)0.08 (5)0.006 (6)0.008 (14)0.004 (15)
C50.030 (7)0.028 (7)0.05 (4)0.013 (6)0.019 (15)0.007 (18)
Geometric parameters (Å, º) top
O4—C41.38 (5)C3—C21.49 (2)
O2—C21.40 (5)C3—C41.51 (3)
O3—C31.44 (3)C2—C11.492 (15)
O1—C11.48 (3)C4—C51.52 (2)
O5—C51.34 (5)
O3—C3—C2109.5 (15)O1—C1—C2110.1 (14)
O3—C3—C4109 (2)O4—C4—C3108.5 (18)
C2—C3—C4117 (4)O4—C4—C5110 (2)
O2—C2—C3115 (5)C3—C4—C5110 (3)
O2—C2—C1107 (3)O5—C5—C4110 (4)
C3—C2—C1108.8 (11)
 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds