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The stable anhydrous form of α-lactose has been obtained by the dehydration of α-lactose monohydrate in methanol. An X-ray powder diffraction pattern was recorded at room temperature with a laboratory diffractometer equipped with an INEL curved sensitive detector CPS120. The starting structural model of this form was found by a Monte-Carlo simulated annealing method. The structure was obtained through Rietveld refinements and the minimization of crystalline energy for the localization of the H atoms of the hydroxyl groups. Soft restraints were applied to bond lengths and angles. Networks of O—H...O hydrogen bonds account for the crystalline cohesion. A comparison is made between the hydrogen-bond networks of this form and those of the monohydrate and hygroscopic anhydrous forms of α-lactose.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768105000455/lc5010sup1.cif
Contains datablocks global, stable_anhydrous_alpha-Lactose

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768105000455/lc5010sup2.rtv
Contains datablock powder

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768105000455/lc5010sup3.pdf
Further structural parameters

CCDC reference: 268161

Experimental top

Crystalline alpha-LS was obtained by dehydration of commercial crystalline alpha-L—H2O purchased from SIGMA Company. Dehydration was performed by blowing dry gaseous methanol through 20 g of alpha-L—H2O during 3 h. Such a dehydration is performed at quite low temperature (64.7°C) which prevents the formation of beta-L by mutarotation. The remaining traces of methanol were then removed by placing the sample under vacuum (10–3 mm H g) at 20°C during 12 h.

Computing details top

Data collection: PEAKOC; program(s) used to solve structure: FOX; program(s) used to refine structure: FULLPROF; molecular graphics: ORTEP-3; software used to prepare material for publication: SHELX97 and PARST.

Figures top
[Figure 1] Fig. 1. : Final Rietveld plot of the stable anhydrous phase of ?–lactose. Observed data points are indicated by dots, the best fit profile (upper trace) and the difference pattern (lower trace) are solid lines. The vertical bars correspond to the position of Bragg peaks.
[Figure 2] Fig. 2. : Atomic numbering and structure of the molecule of alpha–lactose.
[Figure 3] Fig. 3. : Projection along c* of the unit cell of the stable anhydrous form of alpha-lactose. Dashed lines correspond to H bonds.
[Figure 4] Fig. 4. : Strain values on the alpha-LS form for different directions of the lattice: a) in the (b, c*) plane, b), c), d) and e) correspond to planes form by the b x c* direction and direction of an extreme value of the strain in the previous plane, phi is the angle between this direction and b: b) phi = −2°, c) phi = 38°, d) phi =70°, e) phi = 123°. The dotted circles represent the average value of the strain: 15.7x10–4.
4-O-beta-D-galactopyranosyl-D-glucopyranose top
Crystal data top
C12H22O11β = 106.2610 (7)°
Mr = 342.30γ = 97.1529 (8)°
Triclinic, P1V = 720.18 (3) Å3
Hall symbol: P 1Z = 2
a = 7.65217 (17) ÅCu Kα radiation, λ = 1.540560 Å
b = 19.8637 (5) ÅT = 293 K
c = 4.98773 (13) Å?, ? × ? × ? mm
α = 92.0279 (10)°
Data collection top
Enraf Nonius FR 590
diffractometer
Quartz (curved monochromator)
Radiation source: sealed X-ray tubeScan method: Stationary detector
Refinement top
Rp = 2.662Profile function: pseudo-Voigt
Rwp = 3.511195 parameters
Rexp = 1.586118 restraints
RBragg = 1.607
χ2 = NOT FOUNDBackground function: linear interpolation between 30 points
3946 data pointsPreferred orientation correction: March-Dollase function, axis [-2, 1, 0], G1 = 0.965 (3), G2 = 0
Excluded region(s): 0.291 to 8.50 : no Bragg peaks 80.00 to 114.696 : peak intensities too low
Crystal data top
C12H22O11β = 106.2610 (7)°
Mr = 342.30γ = 97.1529 (8)°
Triclinic, P1V = 720.18 (3) Å3
a = 7.65217 (17) ÅZ = 2
b = 19.8637 (5) ÅCu Kα radiation, λ = 1.540560 Å
c = 4.98773 (13) ÅT = 293 K
α = 92.0279 (10)°?, ? × ? × ? mm
Data collection top
Enraf Nonius FR 590
diffractometer
Scan method: Stationary detector
Refinement top
Rp = 2.662χ2 = NOT FOUND
Rwp = 3.5113946 data points
Rexp = 1.586195 parameters
RBragg = 1.607118 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.4157 (11)0.5519 (4)0.824 (3)0.0174 (14)*
C120.2271 (11)0.5730 (4)0.811 (3)0.0174 (14)*
C130.2221 (11)0.6383 (4)0.663 (3)0.0174 (14)*
C140.3910 (11)0.6908 (6)0.783 (2)0.0174 (14)*
C150.5698 (11)0.6604 (4)0.844 (3)0.0174 (14)*
C160.7358 (12)0.7119 (6)0.978 (5)0.0174 (14)*
O110.4130 (16)0.4922 (5)0.971 (3)0.0174 (14)*
O120.0724 (14)0.5241 (6)0.666 (3)0.0174 (14)*
O130.0613 (15)0.6709 (7)0.624 (3)0.0174 (14)*
O140.3914 (18)0.7197 (7)1.047 (2)0.0174 (14)*
O150.5635 (16)0.5998 (4)0.985 (2)0.0174 (14)*
O160.8926 (15)0.6765 (7)1.034 (4)0.0174 (14)*
H110.4309 (11)0.5415 (4)0.635 (3)0.0174 (14)*
H120.2199 (11)0.5838 (4)1.005 (3)0.0174 (14)*
H130.2241 (11)0.6262 (4)0.467 (3)0.0174 (14)*
H140.3956 (11)0.7285 (6)0.657 (2)0.0174 (14)*
H150.5836 (11)0.6463 (4)0.657 (3)0.0174 (14)*
H16a0.7220 (12)0.7317 (6)1.157 (5)0.0174 (14)*
H16b0.7460 (12)0.7504 (6)0.857 (5)0.0174 (14)*
HO120.0047 (14)0.5145 (6)0.792 (3)0.0174 (14)*
HO130.0053 (15)0.6499 (7)0.750 (3)0.0174 (14)*
HO140.2961 (18)0.7501 (7)1.012 (2)0.0174 (14)*
HO160.9615 (15)0.6850 (7)1.233 (4)0.0174 (14)*
C11'0.7648 (14)0.3448 (6)1.1266 (19)0.0174 (14)*
C12'0.8531 (11)0.4137 (4)1.072 (3)0.0174 (14)*
C13'0.7280 (11)0.4677 (4)1.067 (4)0.0174 (14)*
C14'0.5246 (11)0.4421 (4)0.936 (3)0.0174 (14)*
C15'0.4530 (11)0.3749 (4)1.029 (3)0.0174 (14)*
C16'0.2654 (15)0.3496 (11)0.8315 (19)0.0174 (14)*
O11'0.7952 (18)0.3468 (8)1.4218 (18)0.0174 (14)*
O12'1.0406 (12)0.4232 (8)1.241 (3)0.0174 (14)*
O13'0.8298 (18)0.5264 (6)0.993 (3)0.0174 (14)*
O15'0.5724 (11)0.3283 (6)0.977 (3)0.0174 (14)*
O16'0.243 (2)0.3357 (7)0.5373 (19)0.0174 (14)*
H11'0.8321 (14)0.3090 (6)1.0719 (19)0.0174 (14)*
H12'0.8580 (11)0.4081 (4)0.875 (3)0.0174 (14)*
H13'0.7370 (11)0.4775 (4)1.269 (4)0.0174 (14)*
H14'0.5045 (11)0.4353 (4)0.729 (3)0.0174 (14)*
H15'0.4546 (11)0.3787 (4)1.230 (3)0.0174 (14)*
H16a'0.1802 (15)0.3816 (11)0.8599 (19)0.0174 (14)*
H16b'0.2252 (15)0.3050 (11)0.8985 (19)0.0174 (14)*
HO11'0.8259 (18)0.3029 (8)1.4857 (18)0.0174 (14)*
HO12'1.0608 (12)0.4668 (8)1.353 (3)0.0174 (14)*
HO13'0.7971 (18)0.5680 (6)1.068 (3)0.0174 (14)*
HO16'0.228 (2)0.3781 (7)0.4464 (19)0.0174 (14)*
C210.4100 (11)0.0719 (4)0.593 (3)0.0149 (15)*
C220.5985 (10)0.1012 (4)0.568 (3)0.0149 (15)*
C230.6131 (11)0.1781 (4)0.593 (4)0.0149 (15)*
C240.4474 (11)0.2071 (7)0.4090 (19)0.0149 (15)*
C250.2664 (11)0.1668 (4)0.410 (3)0.0149 (15)*
C260.0976 (12)0.1913 (7)0.220 (4)0.0149 (15)*
O210.397950.000680.588760.0149 (15)*
O220.7538 (17)0.0781 (7)0.760 (3)0.0149 (15)*
O230.7820 (13)0.2143 (7)0.579 (3)0.0149 (15)*
O240.4561 (19)0.2065 (7)0.1281 (18)0.0149 (15)*
O250.2659 (18)0.0943 (4)0.380 (3)0.0149 (15)*
O260.0442 (16)0.1411 (6)0.260 (4)0.0149 (15)*
H210.4024 (11)0.0891 (4)0.780 (3)0.0149 (15)*
H220.6013 (10)0.0863 (4)0.375 (3)0.0149 (15)*
H230.6107 (11)0.1892 (4)0.789 (4)0.0149 (15)*
H240.4527 (11)0.2549 (7)0.4840 (19)0.0149 (15)*
H250.2560 (11)0.1767 (4)0.603 (3)0.0149 (15)*
H26a0.1038 (12)0.1897 (7)0.022 (4)0.0149 (15)*
H26b0.0824 (12)0.2390 (7)0.271 (4)0.0149 (15)*
HO220.8236 (17)0.0520 (7)0.667 (3)0.0149 (15)*
HO230.8468 (13)0.1843 (7)0.492 (3)0.0149 (15)*
HO240.5764 (19)0.2071 (7)0.0933 (18)0.0149 (15)*
HO260.1475 (16)0.1401 (6)0.105 (4)0.0149 (15)*
C21'0.0839 (12)0.1633 (5)0.839 (2)0.0149 (15)*
C22'0.0064 (11)0.0984 (5)0.773 (3)0.0149 (15)*
C23'0.0817 (11)0.0496 (5)0.603 (3)0.0149 (15)*
C24'0.2867 (11)0.0308 (5)0.745 (3)0.0149 (15)*
C25'0.3736 (12)0.0956 (5)0.821 (3)0.0149 (15)*
C26'0.5634 (16)0.0800 (6)1.027 (4)0.0149 (15)*
O21'0.0631 (17)0.1952 (7)0.569 (2)0.0149 (15)*
O22'0.1978 (12)0.1115 (7)0.631 (4)0.0149 (15)*
O23'0.0018 (19)0.0120 (6)0.566 (3)0.0149 (15)*
O25'0.2783 (11)0.1420 (7)0.961 (3)0.0149 (15)*
O26'0.6511 (18)0.1406 (5)1.063 (4)0.0149 (15)*
H21'0.0290 (12)0.1916 (5)0.965 (2)0.0149 (15)*
H22'0.0024 (11)0.0735 (5)0.955 (3)0.0149 (15)*
H23'0.0651 (11)0.0735 (5)0.416 (3)0.0149 (15)*
H24'0.3039 (11)0.0019 (5)0.921 (3)0.0149 (15)*
H25'0.3811 (12)0.1195 (5)0.645 (3)0.0149 (15)*
H26a'0.5538 (16)0.0632 (6)1.213 (4)0.0149 (15)*
H26b'0.6403 (16)0.0430 (6)0.963 (4)0.0149 (15)*
HO21'0.0066 (17)0.2410 (7)0.583 (2)0.0149 (15)*
HO22'0.2040 (12)0.1174 (7)0.433 (4)0.0149 (15)*
HO23'0.0383 (19)0.0384 (6)0.424 (3)0.0149 (15)*
HO26'0.7418 (18)0.1046 (5)1.035 (4)0.0149 (15)*
Geometric parameters (Å, º) top
C11—O151.415 (12)C21—O211.406 (9)
C11—O111.416 (15)C21—O251.430 (16)
C11—C121.538 (13)C21—C221.527 (14)
C11—H111.000C21—H211.000
C12—O121.434 (13)C22—O221.439 (16)
C12—C131.516 (15)C22—C231.515 (12)
C12—H121.000C22—H221.000
C13—O131.430 (15)C23—O231.420 (15)
C13—C141.518 (12)C23—C241.533 (14)
C13—H131.000C23—H231.000
C14—O141.415 (16)C24—O241.420 (14)
C14—C151.521 (13)C24—C251.512 (13)
C14—H141.001C24—H241.000
C15—O151.419 (15)C25—O251.441 (12)
C15—C161.503 (12)C25—C261.520 (15)
C15—H151.000C25—H251.000
C16—O161.431 (17)C26—O261.442 (18)
C16—H16A1.001C26—H26A1.000
C16—H16B1.000C26—H26B1.000
O11—C14'1.426 (15)O21—C24'1.414 (12)
O12—HO120.985O22—HO220.980
O13—HO130.986O23—HO230.982
O14—HO140.986O24—HO240.982
O16—HO160.986O26—HO260.938
C11'—O11'1.424 (13)C21'—O21'1.424 (15)
C11'—O15'1.442 (12)C21'—O25'1.442 (12)
C11'—C12'1.517 (15)C21'—C22'1.540 (15)
C11'—H11'1.000C21'—H21'1.000
C12'—O12'1.430 (12)C22'—O22'1.424 (12)
C12'—C13'1.521 (13)C22'—C23'1.525 (18)
C12'—H12'1.000C22'—H22'1.000
C13'—O13'1.438 (18)C23'—O23'1.444 (16)
C13'—C14'1.523 (11)C23'—C24'1.522 (11)
C13'—H13'1.000C23'—H23'1.000
C14'—C15'1.517 (14)C24'—C25'1.532 (14)
C14'—H14'1.000C24'—H24'1.000
C15'—O15'1.444 (15)C25'—O25'1.426 (17)
C15'—C16'1.509 (13)C25'—C26'1.515 (15)
C15'—H15'1.000C25'—H25'1.000
C16'—O16'1.441 (14)C26'—O26'1.443 (17)
C16'—H16A'0.999C26'—H26A'1.000
C16'—H16B'1.001C26'—H26B'1.000
O11'—HO11'0.974O21'—HO21'0.972
O12'—HO12'0.985O22'—HO22'0.979
O13'—HO13'0.984O23'—HO23'0.987
O16'—HO16'0.975O26'—HO26'0.976
O15—C11—O11107.7 (8)O21—C21—O25112.9 (7)
O15—C11—C12112.6 (9)O21—C21—C22108.9 (7)
O11—C11—C12101.7 (8)O25—C21—C22111.1 (9)
O15—C11—H11110.7O21—C21—H21107.9
O11—C11—H11110.5O25—C21—H21108.6
C12—C11—H11113.1C22—C21—H21107.3
O12—C12—C13109.8 (8)O22—C22—C23111.2 (9)
O12—C12—C11114.8 (9)O22—C22—C21115.8 (9)
C13—C12—C11104.7 (7)C23—C22—C21107.8 (7)
O12—C12—H12109.3O22—C22—H22106.3
C13—C12—H12108.0C23—C22—H22108.7
C11—C12—H12110.0C21—C22—H22106.6
O13—C13—C12117.4 (9)O23—C23—C22115.8 (9)
O13—C13—C14109.0 (9)O23—C23—C24111.7 (9)
C12—C13—C14113.7 (8)C22—C23—C24114.8 (8)
O13—C13—H13103.7O23—C23—H23104.1
C12—C13—H13106.9C22—C23—H23104.3
C14—C13—H13104.8C24—C23—H23104.4
O14—C14—C13110.9 (10)O24—C24—C25108.2 (9)
O14—C14—C15104.1 (9)O24—C24—C23109.8 (9)
C13—C14—C15113.1 (8)C25—C24—C23112.4 (8)
O14—C14—H14107.9O24—C24—H24109.9
C13—C14—H14111.3C25—C24—H24108.9
C15—C14—H14109.3C23—C24—H24107.7
O15—C15—C16113.9 (8)O25—C25—C24112.8 (9)
O15—C15—C14112.8 (9)O25—C25—C26113.8 (9)
C16—C15—C14112.8 (8)C24—C25—C26114.6 (8)
O15—C15—H15105.4O25—C25—H25106.0
C16—C15—H15105.1C24—C25—H25104.7
C14—C15—H15105.9C26—C25—H25103.7
O16—C16—C15107.1 (10)O26—C26—C2599.9 (9)
O16—C16—H16A110.4O26—C26—H26A112.5
C15—C16—H16A108.5C25—C26—H26A110.1
O16—C16—H16B112.4O26—C26—H26B113.3
C15—C16—H16B111.5C25—C26—H26B114.1
H16A—C16—H16B107.0H26A—C26—H26B107.0
C11—O11—C14'119.8 (8)C21—O21—C24'115.1 (6)
C12—O12—HO12107.8C22—O22—HO22113.2
C13—O13—HO13105.9C23—O23—HO23109.7
C14—O14—HO14107.2C24—O24—HO24118.7
C11—O15—C15109.1 (8)C21—O25—C25112.0 (8)
C16—O16—HO16109.0C26—O26—HO26107.2
O11'—C11'—O15'111.9 (9)O21'—C21'—O25'106.3 (9)
O11'—C11'—C12'105.0 (10)O21'—C21'—C22'103.6 (9)
O15'—C11'—C12'114.3 (9)O25'—C21'—C22'107.1 (8)
O11'—C11'—H11'108.4O21'—C21'—H21'115.2
O15'—C11'—H11'108.5O25'—C21'—H21'112.1
C12'—C11'—H11'108.5C22'—C21'—H21'111.9
O12'—C12'—C11'107.4 (9)O22'—C22'—C23'107.1 (9)
O12'—C12'—C13'122.2 (9)O22'—C22'—C21'113.7 (9)
C11'—C12'—C13'111.5 (8)C23'—C22'—C21'114.8 (9)
O12'—C12'—H12'105.3O22'—C22'—H22'105.2
C11'—C12'—H12'104.4C23'—C22'—H22'107.9
C13'—C12'—H12'104.3C21'—C22'—H22'107.7
O13'—C13'—C12'102.5 (8)O23'—C23'—C24'108.7 (9)
O13'—C13'—C14'126.0 (9)O23'—C23'—C22'111.6 (9)
C12'—C13'—C14'114.1 (8)C24'—C23'—C22'110.8 (8)
O13'—C13'—H13'105.0O23'—C23'—H23'109.5
C12'—C13'—H13'103.8C24'—C23'—H23'108.4
C14'—C13'—H13'103.2C22'—C23'—H23'107.7
O11—C14'—C15'109.6 (7)O21—C24'—C23'118.4 (7)
O11—C14'—C13'111.4 (9)O21—C24'—C25'101.6 (8)
C15'—C14'—C13'116.1 (7)C23'—C24'—C25'109.5 (8)
O11—C14'—H14'105.3O21—C24'—H24'109.4
C15'—C14'—H14'106.7C23'—C24'—H24'108.7
C13'—C14'—H14'107.0C25'—C24'—H24'108.8
O15'—C15'—C16'105.6 (9)O25'—C25'—C26'102.8 (9)
O15'—C15'—C14'104.4 (8)O25'—C25'—C24'114.7 (9)
C16'—C15'—C14'108.5 (9)C26'—C25'—C24'111.7 (9)
O15'—C15'—H15'112.4O25'—C25'—H25'108.8
C16'—C15'—H15'113.5C26'—C25'—H25'109.9
C14'—C15'—H15'111.8C24'—C25'—H25'108.8
O16'—C16'—C15'120.2 (9)O26'—C26'—C25'110.1 (11)
O16'—C16'—H16A'110.6O26'—C26'—H26A'108.4
C15'—C16'—H16A'107.4C25'—C26'—H26A'110.0
O16'—C16'—H16B'105.2O26'—C26'—H26B'110.5
C15'—C16'—H16B'105.5C25'—C26'—H26B'110.7
H16A'—C16'—H16B'107.0H26A'—C26'—H26B'107.0
C11'—O11'—HO11'108.5C21'—O21'—HO21'102.5
C12'—O12'—HO12'106.7C22'—O22'—HO22'104.6
C13'—O13'—HO13'109.5C23'—O23'—HO23'110.3
C11'—O15'—C15'116.3 (9)C25'—O25'—C21'119.0 (9)
C16'—O16'—HO16'108.1C26'—O26'—HO26'73.7
O15—C11—C12—O12176.0 (10)O21—C21—C22—O2250.8 (13)
O11—C11—C12—O1261.0 (12)O25—C21—C22—O22175.7 (11)
O15—C11—C12—C1363.5 (11)O21—C21—C22—C23176.1 (8)
O11—C11—C12—C13178.5 (9)O25—C21—C22—C2359.0 (12)
O12—C12—C13—O1357.2 (14)O22—C22—C23—O2351.0 (15)
C11—C12—C13—O13179.0 (10)C21—C22—C23—O23179.0 (10)
O12—C12—C13—C14173.9 (10)O22—C22—C23—C24176.3 (10)
C11—C12—C13—C1450.1 (12)C21—C22—C23—C2448.3 (13)
O13—C13—C14—O1461.0 (13)O23—C23—C24—O2456.7 (14)
C12—C13—C14—O1472.0 (12)C22—C23—C24—O2477.8 (13)
O13—C13—C14—C15177.4 (10)O23—C23—C24—C25177.1 (10)
C12—C13—C14—C1544.4 (13)C22—C23—C24—C2542.6 (13)
O14—C14—C15—O1574.3 (12)O24—C24—C25—O2576.5 (13)
C13—C14—C15—O1546.0 (13)C23—C24—C25—O2544.8 (13)
O14—C14—C15—C1656.5 (13)O24—C24—C25—C2655.9 (13)
C13—C14—C15—C16176.8 (10)C23—C24—C25—C26177.2 (10)
O15—C15—C16—O1647.6 (15)O25—C25—C26—O2645.3 (14)
C14—C15—C16—O16177.8 (11)C24—C25—C26—O26177.1 (11)
O15—C11—O11—C14'85.9 (13)O25—C21—O21—C24'87.3 (10)
C12—C11—O11—C14'155.6 (11)C22—C21—O21—C24'148.8 (8)
O11—C11—O15—C15179.9 (10)O21—C21—O25—C25172.3 (9)
C12—C11—O15—C1568.6 (12)C22—C21—O25—C2565.1 (13)
C16—C15—O15—C11172.7 (10)C24—C25—O25—C2157.1 (13)
C14—C15—O15—C1157.1 (12)C26—C25—O25—C21170.2 (11)
O11'—C11'—C12'—O12'55.3 (12)O21'—C21'—C22'—O22'63.3 (12)
O15'—C11'—C12'—O12'178.4 (10)O25'—C21'—C22'—O22'175.4 (10)
O11'—C11'—C12'—C13'81.1 (12)O21'—C21'—C22'—C23'60.4 (12)
O15'—C11'—C12'—C13'42.0 (14)O25'—C21'—C22'—C23'51.6 (12)
O12'—C12'—C13'—O13'55.2 (15)O22'—C22'—C23'—O23'56.8 (13)
C11'—C12'—C13'—O13'175.8 (10)C21'—C22'—C23'—O23'176.0 (10)
O12'—C12'—C13'—C14'165.4 (11)O22'—C22'—C23'—C24'178.2 (10)
C11'—C12'—C13'—C14'36.4 (14)C21'—C22'—C23'—C24'54.7 (12)
C11—O11—C14'—C15'160.9 (10)C21—O21—C24'—C23'87.0 (10)
C11—O11—C14'—C13'69.1 (14)C21—O21—C24'—C25'153.0 (8)
O13'—C13'—C14'—O1159.7 (17)O23'—C23'—C24'—O2171.5 (12)
C12'—C13'—C14'—O11172.2 (10)C22'—C23'—C24'—O21165.5 (9)
O13'—C13'—C14'—C15'173.9 (12)O23'—C23'—C24'—C25'172.8 (10)
C12'—C13'—C14'—C15'45.8 (14)C22'—C23'—C24'—C25'49.7 (12)
O11—C14'—C15'—O15'178.3 (10)O21—C24'—C25'—O25'174.5 (9)
C13'—C14'—C15'—O15'54.4 (13)C23'—C24'—C25'—O25'48.5 (13)
O11—C14'—C15'—C16'66.1 (12)O21—C24'—C25'—C26'69.1 (11)
C13'—C14'—C15'—C16'166.6 (11)C23'—C24'—C25'—C26'164.9 (10)
O15'—C15'—C16'—O16'51.0 (15)O25'—C25'—C26'—O26'64.6 (13)
C14'—C15'—C16'—O16'60.4 (15)C24'—C25'—C26'—O26'171.9 (11)
O11'—C11'—O15'—C15'60.6 (14)C26'—C25'—O25'—C21'173.5 (10)
C12'—C11'—O15'—C15'58.6 (14)C24'—C25'—O25'—C21'52.1 (14)
C16'—C15'—O15'—C11'175.4 (10)O21'—C21'—O25'—C25'59.6 (13)
C14'—C15'—O15'—C11'61.1 (12)C22'—C21'—O25'—C25'50.6 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—HO12···O13i0.99 (2)1.85 (2)2.80 (2)159.4 (14)
O13—HO13···O16i0.99 (2)1.89 (2)2.71 (2)139.2 (15)
O14—HO14···O25?ii0.99 (2)2.18 (2)2.99 (2)138.0 (14)
O16—HO16···O13iii0.99 (2)1.93 (2)2.88 (2)161.0 (18)
O11?—HO11?···O23iv0.97 (2)1.85 (2)2.77 (2)157 (2)
O12?—HO12?···O12iii0.99 (2)1.87 (2)2.80 (2)156 (2)
O13?—HO13?···O150.98 (2)1.91 (2)2.643 (19)129 (1)
O16?—HO16?···O12?v0.98 (2)1.86 (2)2.679 (19)140 (1)
O22—HO22···O23?vi0.98 (2)1.81 (2)2.77 (2)166.3 (15)
O23—HO23···O26vi0.98 (2)1.85 (2)2.81 (2)166.5 (14)
O24—HO24···O15?vii0.98 (2)2.449 (19)2.681 (18)89.8 (12)
O26—HO26···O22v0.938 (19)1.98 (2)2.706 (19)132.3 (17)
O21—HO21?···O13viii0.97 (2)1.86 (2)2.683 (19)141 (1)
O22?—HO22?···O26?v0.98 (3)1.87 (2)2.75 (2)148 (2)
O23?—HO23?···O250.99 (2)2.02 (2)2.84 (2)140 (1)
O26?—HO26?···O22?vi0.98 (2)2.19 (3)2.76 (3)116 (2)
Symmetry codes: (i) x1, y, z; (ii) x, y+1, z; (iii) x+1, y, z+1; (iv) x, y, z+1; (v) x1, y, z1; (vi) x+1, y, z; (vii) x, y, z1; (viii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC12H22O11
Mr342.30
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.65217 (17), 19.8637 (5), 4.98773 (13)
α, β, γ (°)92.0279 (10), 106.2610 (7), 97.1529 (8)
V3)720.18 (3)
Z2
Radiation typeCu Kα, λ = 1.540560 Å
Specimen shape, size (mm)?, ? × ? × ?
Data collection
DiffractometerEnraf Nonius FR 590
diffractometer
Specimen mounting?
Data collection mode?
Scan methodStationary detector
2θ values (°)2θfixed = ?
Refinement
R factors and goodness of fitRp = 2.662, Rwp = 3.511, Rexp = 1.586, RBragg = 1.607, χ2 = NOT FOUND
No. of data points3946
No. of parameters195
No. of restraints118

Computer programs: PEAKOC, FOX, FULLPROF, ORTEP-3, SHELX97 and PARST.

Selected geometric parameters (Å, º) top
C11—O151.415 (12)C21—O211.406 (9)
C11—O111.416 (15)C21—O251.430 (16)
C11—C121.538 (13)C21—C221.527 (14)
C12—O121.434 (13)C22—O221.439 (16)
C12—C131.516 (15)C22—C231.515 (12)
C13—O131.430 (15)C23—O231.420 (15)
C13—C141.518 (12)C23—C241.533 (14)
C14—O141.415 (16)C24—O241.420 (14)
C14—C151.521 (13)C24—C251.512 (13)
C15—O151.419 (15)C25—O251.441 (12)
C15—C161.503 (12)C25—C261.520 (15)
C16—O161.431 (17)C26—O261.442 (18)
O11—C14'1.426 (15)O21—C24'1.414 (12)
C11'—O11'1.424 (13)C21'—O21'1.424 (15)
C11'—O15'1.442 (12)C21'—O25'1.442 (12)
C11'—C12'1.517 (15)C21'—C22'1.540 (15)
C12'—O12'1.430 (12)C22'—O22'1.424 (12)
C12'—C13'1.521 (13)C22'—C23'1.525 (18)
C13'—O13'1.438 (18)C23'—O23'1.444 (16)
C13'—C14'1.523 (11)C23'—C24'1.522 (11)
C14'—C15'1.517 (14)C24'—C25'1.532 (14)
C15'—O15'1.444 (15)C25'—O25'1.426 (17)
C15'—C16'1.509 (13)C25'—C26'1.515 (15)
C16'—O16'1.441 (14)C26'—O26'1.443 (17)
O15—C11—O11107.7 (8)O21—C21—O25112.9 (7)
O15—C11—C12112.6 (9)O21—C21—C22108.9 (7)
O11—C11—C12101.7 (8)O25—C21—C22111.1 (9)
O12—C12—C13109.8 (8)O22—C22—C23111.2 (9)
O12—C12—C11114.8 (9)O22—C22—C21115.8 (9)
C13—C12—C11104.7 (7)C23—C22—C21107.8 (7)
O13—C13—C12117.4 (9)O23—C23—C22115.8 (9)
O13—C13—C14109.0 (9)O23—C23—C24111.7 (9)
C12—C13—C14113.7 (8)C22—C23—C24114.8 (8)
O14—C14—C13110.9 (10)O24—C24—C25108.2 (9)
O14—C14—C15104.1 (9)O24—C24—C23109.8 (9)
C13—C14—C15113.1 (8)C25—C24—C23112.4 (8)
O15—C15—C16113.9 (8)O25—C25—C24112.8 (9)
O15—C15—C14112.8 (9)O25—C25—C26113.8 (9)
C16—C15—C14112.8 (8)C24—C25—C26114.6 (8)
O16—C16—C15107.1 (10)O26—C26—C2599.9 (9)
C11—O11—C14'119.8 (8)C21—O21—C24'115.1 (6)
C11—O15—C15109.1 (8)C21—O25—C25112.0 (8)
O11'—C11'—O15'111.9 (9)O21'—C21'—O25'106.3 (9)
O11'—C11'—C12'105.0 (10)O21'—C21'—C22'103.6 (9)
O15'—C11'—C12'114.3 (9)O25'—C21'—C22'107.1 (8)
O12'—C12'—C11'107.4 (9)O22'—C22'—C23'107.1 (9)
O12'—C12'—C13'122.2 (9)O22'—C22'—C21'113.7 (9)
C11'—C12'—C13'111.5 (8)C23'—C22'—C21'114.8 (9)
O13'—C13'—C12'102.5 (8)O23'—C23'—C24'108.7 (9)
O13'—C13'—C14'126.0 (9)O23'—C23'—C22'111.6 (9)
C12'—C13'—C14'114.1 (8)C24'—C23'—C22'110.8 (8)
O11—C14'—C15'109.6 (7)O21—C24'—C23'118.4 (7)
O11—C14'—C13'111.4 (9)O21—C24'—C25'101.6 (8)
C15'—C14'—C13'116.1 (7)C23'—C24'—C25'109.5 (8)
O15'—C15'—C16'105.6 (9)O25'—C25'—C26'102.8 (9)
O15'—C15'—C14'104.4 (8)O25'—C25'—C24'114.7 (9)
C16'—C15'—C14'108.5 (9)C26'—C25'—C24'111.7 (9)
O16'—C16'—C15'120.2 (9)O26'—C26'—C25'110.1 (11)
C11'—O15'—C15'116.3 (9)C25'—O25'—C21'119.0 (9)
O15—C11—C12—O12176.0 (10)O21—C21—C22—O2250.8 (13)
O11—C11—C12—O1261.0 (12)O25—C21—C22—O22175.7 (11)
O15—C11—C12—C1363.5 (11)O21—C21—C22—C23176.1 (8)
O11—C11—C12—C13178.5 (9)O25—C21—C22—C2359.0 (12)
O12—C12—C13—O1357.2 (14)O22—C22—C23—O2351.0 (15)
C11—C12—C13—O13179.0 (10)C21—C22—C23—O23179.0 (10)
O12—C12—C13—C14173.9 (10)O22—C22—C23—C24176.3 (10)
C11—C12—C13—C1450.1 (12)C21—C22—C23—C2448.3 (13)
O13—C13—C14—O1461.0 (13)O23—C23—C24—O2456.7 (14)
C12—C13—C14—O1472.0 (12)C22—C23—C24—O2477.8 (13)
O13—C13—C14—C15177.4 (10)O23—C23—C24—C25177.1 (10)
C12—C13—C14—C1544.4 (13)C22—C23—C24—C2542.6 (13)
O14—C14—C15—O1574.3 (12)O24—C24—C25—O2576.5 (13)
C13—C14—C15—O1546.0 (13)C23—C24—C25—O2544.8 (13)
O14—C14—C15—C1656.5 (13)O24—C24—C25—C2655.9 (13)
C13—C14—C15—C16176.8 (10)C23—C24—C25—C26177.2 (10)
O15—C15—C16—O1647.6 (15)O25—C25—C26—O2645.3 (14)
C14—C15—C16—O16177.8 (11)C24—C25—C26—O26177.1 (11)
O15—C11—O11—C14'85.9 (13)O25—C21—O21—C24'87.3 (10)
C12—C11—O11—C14'155.6 (11)C22—C21—O21—C24'148.8 (8)
O11—C11—O15—C15179.9 (10)O21—C21—O25—C25172.3 (9)
C12—C11—O15—C1568.6 (12)C22—C21—O25—C2565.1 (13)
C16—C15—O15—C11172.7 (10)C24—C25—O25—C2157.1 (13)
C14—C15—O15—C1157.1 (12)C26—C25—O25—C21170.2 (11)
O11'—C11'—C12'—O12'55.3 (12)O21'—C21'—C22'—O22'63.3 (12)
O15'—C11'—C12'—O12'178.4 (10)O25'—C21'—C22'—O22'175.4 (10)
O11'—C11'—C12'—C13'81.1 (12)O21'—C21'—C22'—C23'60.4 (12)
O15'—C11'—C12'—C13'42.0 (14)O25'—C21'—C22'—C23'51.6 (12)
O12'—C12'—C13'—O13'55.2 (15)O22'—C22'—C23'—O23'56.8 (13)
C11'—C12'—C13'—O13'175.8 (10)C21'—C22'—C23'—O23'176.0 (10)
O12'—C12'—C13'—C14'165.4 (11)O22'—C22'—C23'—C24'178.2 (10)
C11'—C12'—C13'—C14'36.4 (14)C21'—C22'—C23'—C24'54.7 (12)
C11—O11—C14'—C15'160.9 (10)C21—O21—C24'—C23'87.0 (10)
C11—O11—C14'—C13'69.1 (14)C21—O21—C24'—C25'153.0 (8)
O13'—C13'—C14'—O1159.7 (17)O23'—C23'—C24'—O2171.5 (12)
C12'—C13'—C14'—O11172.2 (10)C22'—C23'—C24'—O21165.5 (9)
O13'—C13'—C14'—C15'173.9 (12)O23'—C23'—C24'—C25'172.8 (10)
C12'—C13'—C14'—C15'45.8 (14)C22'—C23'—C24'—C25'49.7 (12)
O11—C14'—C15'—O15'178.3 (10)O21—C24'—C25'—O25'174.5 (9)
C13'—C14'—C15'—O15'54.4 (13)C23'—C24'—C25'—O25'48.5 (13)
O11—C14'—C15'—C16'66.1 (12)O21—C24'—C25'—C26'69.1 (11)
C13'—C14'—C15'—C16'166.6 (11)C23'—C24'—C25'—C26'164.9 (10)
O15'—C15'—C16'—O16'51.0 (15)O25'—C25'—C26'—O26'64.6 (13)
C14'—C15'—C16'—O16'60.4 (15)C24'—C25'—C26'—O26'171.9 (11)
O11'—C11'—O15'—C15'60.6 (14)C26'—C25'—O25'—C21'173.5 (10)
C12'—C11'—O15'—C15'58.6 (14)C24'—C25'—O25'—C21'52.1 (14)
C16'—C15'—O15'—C11'175.4 (10)O21'—C21'—O25'—C25'59.6 (13)
C14'—C15'—O15'—C11'61.1 (12)C22'—C21'—O25'—C25'50.6 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—HO12···O13'i0.985 (21)1.852 (22)2.797 (23)159.4 (14)
O13—HO13···O16i0.986 (22)1.887 (24)2.711 (24)139.2 (15)
O14—HO14···O25?ii0.986 (21)2.184 (20)2.991 (20)138.0 (14)
O16—HO16···O13iii0.986 (22)1.928 (22)2.878 (22)161.0 (18)
O11?—HO11?···O23iv0.974 (21)1.850 (21)2.771 (21)156.7 (16)
O12?—HO12?···O12iii0.985 (21)1.874 (21)2.803 (20)156.2 (16)
O13?—HO13?···O150.984 (20)1.911 (18)2.643 (19)128.9 (14)
O16?—HO16?···O12?v0.975 (19)1.862 (18)2.679 (19)139.5 (13)
O22—HO22···O23?vi0.980 (22)1.811 (22)2.773 (22)166.3 (15)
O23—HO23···O26vi0.982 (21)1.849 (23)2.813 (22)166.5 (14)
O24—HO24···O15?vii0.982 (21)2.449 (19)2.681 (18)89.8 (12)
O26—HO26···O22v0.938 (19)1.984 (20)2.706 (19)132.3 (17)
O21'—HO21?···O13viii0.972 (18)1.855 (19)2.683 (19)141.4 (14)
O22?—HO22?···O26?v0.979 (25)1.872 (22)2.752 (24)148.0 (19)
O23?—HO23?···O250.987 (22)2.017 (19)2.841 (20)139.5 (14)
O26?—HO26?···O22?vi0.976 (19)2.192 (27)2.763 (26)116.1 (15)
Symmetry codes: (i) x1, y, z; (ii) x, y+1, z; (iii) x+1, y, z+1; (iv) x, y, z+1; (v) x1, y, z1; (vi) x+1, y, z; (vii) x, y, z1; (viii) x, y1, z.
 

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