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The mixed form of α/β lactose was obtained by heating amorphous α-lactose at 443 K. NMR spectroscopy determined the stoichiometry of this mixed compound to be 1/1. The X-ray powder diffraction pattern was recorded at room temperature with a sensitive curved detector (CPS 120). The structure was solved by real-space methods (simulated annealing) followed by Rietveld refinements with soft constraints on bond lengths and bond angles. The H atoms of the hydroxyl groups were localized by minimization of the crystalline energy. The cell of 1/1 α/β lactose is triclinic with the space group P1 and contains two molecules (one molecule of each anomer). The crystalline cohesion is achieved by networks of O—H...O hydrogen bonds. The width of the Bragg peaks is interpreted through a microstructural approach in terms of isotropic strain effects and anisotropic size effects.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768105017064/lc5025sup1.cif
Contains datablocks global, Phase_mixte_alpha-beta_lactose

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768105017064/lc5025sup2.rtv
Contains datablock lact-mixed

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768105017064/lc5025sup3.pdf
Coordinates and geometry

CCDC reference: 280364

Experimental top

The crystalline alpha/beta lactose was obtained in three steps: (i) Crystalline alphaLS was first produced by dehydration of commercial crystalline alphaL-H2O purchased from SIGMA Company. Dehydration was performed by blowing dry gaseous methanol through 20 g of alphaL-H2O during 3 h. Such a dehydration is done at quite low temperature (64.7°C) preventing the formation of betaL 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. (ii) alphaL was then totally amorphized at room temperature by a 23 h milling procedure performed under a dry nitrogen atmosphere in a planetary mill (Pulverisette 7 / Fritsch). (iii) Amorphous alphaLS was then heated up to 170°C at 2°C/min, kept 10 minutes at this temperature, and then cooled down to room temperature. This thermal treatment induces both a strong mutarotation process and the complete crystallization of amorphous alphaL towards the mixed compound alpha/betaL.

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. : 13 C CPMAS spectrum of: (a) mixed lactose, (b) beta–lactose, (c) anhydrous stable alpha–lactose. The lines marked by a star are assigned to residual amorphous lactose.
[Figure 2] Fig. 2. : Final Rietveld plot of the mixed phase of alpha/beta–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 3] Fig. 3. : Atomic numbering and structure of the molecules of alpha and beta–lactose. The notation of atoms Xin is such as: X = C, O; i = 1, 2 for molecules alpha and beta–lactose, respectively; n is the number of the atom; unprimed atoms correspond to the galactose unit, primed atoms for the glucose unit. Dashed lines correspond to intramolecular hydrogen bonds.
[Figure 4] Fig. 4. : Projection along c* of the unit cell of the mixed phase of alpha/beta–lactose. Dashed lines correspond to hydrogen bonds.
[Figure 5] Fig. 5. : Average shape of the crystallites of mixed 1/1 alpha/beta-lactose: a) in the (b, c*) plane; b) in the (b, bxc*) plane, c) in the (c*, bxc*) plane. The dashed circle corresponds to the average diameter of 563 Å.
4-O-beta-D-galactopyranosyl-D-glucopyranose top
Crystal data top
C12H22O11β = 105.430 (2)°
Mr = 342.30γ = 80.996 (2)°
Triclinic, P1V = 721.00 (7) Å3
Hall symbol: P 1Z = 2
a = 7.6258 (4) ÅCu Kα radiation, λ = 1.540560 Å
b = 19.6559 (10) ÅT = 295 K
c = 5.0613 (3) Å?, ? × ? × ? mm
α = 95.646 (2)°
Data collection top
Enraf Nonius FR 590
diffractometer
Quartz (curved monochromator)
Radiation source: sealed X-ray tubeScan method: Stationary detector
Refinement top
Rp = 2.469Profile function: pseudo-Voigt
Rwp = 3.372182 parameters
Rexp = 2.294124 restraints
RBragg = 3.044
χ2 = NOT FOUNDBackground function: linear interpolation between 24 points
3946 data pointsPreferred orientation correction: March-Dollase function, axis [1 , 0, 0], G1 = 0.953 (5), G2 = 0
Excluded region(s): 0.299 to 7.00 : no Bragg peaks 70.00 to 114.704 : peak intensities too low
Crystal data top
C12H22O11β = 105.430 (2)°
Mr = 342.30γ = 80.996 (2)°
Triclinic, P1V = 721.00 (7) Å3
a = 7.6258 (4) ÅZ = 2
b = 19.6559 (10) ÅCu Kα radiation, λ = 1.540560 Å
c = 5.0613 (3) ÅT = 295 K
α = 95.646 (2)°?, ? × ? × ? mm
Data collection top
Enraf Nonius FR 590
diffractometer
Scan method: Stationary detector
Refinement top
Rp = 2.469χ2 = NOT FOUND
Rwp = 3.3723946 data points
Rexp = 2.294182 parameters
RBragg = 3.044124 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.5276 (12)0.0439 (5)0.743 (3)0.030 (4)*
C120.7042 (11)0.0766 (5)0.781 (3)0.030 (4)*
C130.7147 (12)0.1294 (6)1.020 (3)0.030 (4)*
C140.5416 (11)0.1821 (5)0.992 (3)0.030 (4)*
C150.3692 (12)0.1488 (5)0.890 (3)0.030 (4)*
C160.2116 (15)0.1994 (5)0.750 (5)0.030 (4)*
O110.500000.000000.500000.030 (4)*
O120.865 (2)0.0296 (9)0.856 (5)0.030 (4)*
O130.870 (2)0.1617 (10)1.055 (5)0.030 (4)*
O140.537 (3)0.2325 (9)0.814 (4)0.030 (4)*
O150.384 (2)0.0989 (8)0.671 (3)0.030 (4)*
O160.073 (3)0.1562 (12)0.628 (5)0.030 (4)*
H110.5226 (12)0.0211 (5)0.908 (3)0.030 (4)*
H120.6995 (11)0.0999 (5)0.612 (3)0.030 (4)*
H130.7276 (12)0.1047 (6)1.190 (3)0.030 (4)*
H140.5416 (11)0.2063 (5)1.176 (3)0.030 (4)*
H150.3396 (12)0.1285 (5)1.044 (3)0.030 (4)*
H16a0.2474 (15)0.2265 (5)0.620 (5)0.030 (4)*
H16b0.1664 (15)0.2334 (5)0.886 (5)0.030 (4)*
HO120.934 (2)0.0403 (9)1.045 (5)0.030 (4)*
HO130.891 (2)0.1665 (10)0.874 (5)0.030 (4)*
HO140.651 (3)0.2526 (9)0.887 (4)0.030 (4)*
HO160.127 (3)0.1108 (12)0.566 (5)0.030 (4)*
C11'0.1795 (14)0.1628 (7)0.2022 (19)0.111 (6)*
C12'0.0767 (13)0.0948 (4)0.285 (3)0.111 (6)*
C13'0.1876 (11)0.0342 (4)0.298 (3)0.111 (6)*
C14'0.3860 (11)0.0527 (5)0.465 (3)0.111 (6)*
C15'0.4651 (12)0.1142 (5)0.310 (3)0.111 (6)*
C16'0.6648 (18)0.135 (2)0.427 (3)0.111 (6)*
O11'0.149 (4)0.1560 (17)0.082 (2)0.111 (6)*
O12'0.086 (2)0.0870 (10)0.065 (4)0.111 (6)*
O13'0.099 (4)0.0274 (12)0.402 (8)0.111 (6)*
O15'0.3732 (15)0.1710 (9)0.333 (6)0.111 (6)*
O16'0.728 (4)0.1650 (11)0.193 (4)0.111 (6)*
H11'0.1235 (14)0.2036 (7)0.2285 (19)0.111 (6)*
H12'0.0464 (13)0.0997 (4)0.462 (3)0.111 (6)*
H13'0.1878 (11)0.0247 (4)0.107 (3)0.111 (6)*
H14'0.3875 (11)0.0679 (5)0.648 (3)0.111 (6)*
H15'0.4406 (12)0.1035 (5)0.113 (3)0.111 (6)*
H16a'0.6900 (18)0.167 (2)0.577 (3)0.111 (6)*
H16b'0.7265 (18)0.094 (2)0.508 (3)0.111 (6)*
HO11'0.266 (4)0.1771 (17)0.117 (2)0.111 (6)*
HO12'0.053 (2)0.0807 (10)0.103 (4)0.111 (6)*
HO13'0.022 (4)0.0193 (12)0.414 (8)0.111 (6)*
HO16'0.716 (4)0.1287 (11)0.066 (4)0.111 (6)*
C210.5147 (12)0.5588 (5)0.563 (3)0.037 (5)*
C220.3304 (11)0.5882 (5)0.637 (3)0.037 (5)*
C230.3207 (11)0.6665 (5)0.637 (3)0.037 (5)*
C240.4896 (12)0.6942 (9)0.8248 (18)0.037 (5)*
C250.6633 (12)0.6591 (5)0.742 (3)0.037 (5)*
C260.8376 (15)0.6874 (6)0.909 (5)0.037 (5)*
O210.545 (3)0.4849 (5)0.525 (4)0.037 (5)*
O220.165 (2)0.5729 (12)0.444 (5)0.037 (5)*
O230.159 (2)0.6957 (12)0.710 (5)0.037 (5)*
O240.502 (3)0.6858 (11)1.109 (2)0.037 (5)*
O250.670 (2)0.5854 (5)0.758 (4)0.037 (5)*
O260.973 (2)0.6328 (9)1.017 (5)0.037 (5)*
H210.5062 (12)0.5763 (5)0.381 (3)0.037 (5)*
H220.3338 (11)0.5749 (5)0.824 (3)0.037 (5)*
H230.3071 (11)0.6792 (5)0.445 (3)0.037 (5)*
H240.4786 (12)0.7446 (9)0.7990 (18)0.037 (5)*
H250.6483 (12)0.6685 (5)0.547 (3)0.037 (5)*
H26a0.8110 (15)0.7204 (6)1.061 (5)0.037 (5)*
H26b0.8880 (15)0.7135 (6)0.792 (5)0.037 (5)*
HO220.135 (2)0.5307 (12)0.503 (5)0.037 (5)*
HO230.101 (2)0.6564 (12)0.739 (5)0.037 (5)*
HO240.421 (3)0.7258 (11)1.160 (2)0.037 (5)*
HO260.971 (2)0.6222 (9)1.202 (5)0.037 (5)*
C21'0.8152 (12)0.3286 (6)0.156 (3)0.042 (4)*
C22'0.9214 (11)0.3901 (6)0.268 (3)0.042 (4)*
C23'0.8280 (11)0.4363 (7)0.462 (3)0.042 (4)*
C24'0.6268 (12)0.4588 (7)0.307 (2)0.042 (4)*
C25'0.5272 (11)0.3980 (7)0.142 (3)0.042 (4)*
C26'0.330 (2)0.4074 (6)0.037 (6)0.042 (4)*
O21'0.904 (3)0.2855 (9)0.029 (4)0.042 (4)*
O22'1.1121 (14)0.3737 (13)0.391 (4)0.042 (4)*
O23'0.940 (3)0.4892 (10)0.591 (6)0.042 (4)*
O25'0.6338 (18)0.3530 (13)0.007 (3)0.042 (4)*
O26'0.263 (3)0.3418 (7)0.123 (4)0.042 (4)*
H21'0.8081 (12)0.3025 (6)0.312 (3)0.042 (4)*
H22'0.9068 (11)0.4171 (6)0.104 (3)0.042 (4)*
H23'0.8252 (11)0.4072 (7)0.612 (3)0.042 (4)*
H24'0.6188 (12)0.4959 (7)0.181 (2)0.042 (4)*
H25'0.5184 (11)0.3695 (7)0.290 (3)0.042 (4)*
H26a'0.327 (2)0.4337 (6)0.198 (6)0.042 (4)*
H26b'0.247 (2)0.4358 (6)0.067 (6)0.042 (4)*
HO21'0.837 (3)0.2973 (9)0.217 (4)0.042 (4)*
HO22'1.1594 (14)0.3368 (13)0.271 (4)0.042 (4)*
HO23'0.887 (3)0.5190 (10)0.725 (6)0.042 (4)*
HO26'0.139 (3)0.3513 (7)0.239 (4)0.042 (4)*
Geometric parameters (Å, º) top
C11—O151.413 (17)C21—O211.438 (14)
C11—O111.418 (11)C21—O251.455 (19)
C11—C121.540 (14)C21—C221.559 (15)
C11—H111.000C21—H211.000
C12—O121.401 (17)C22—O221.429 (19)
C12—C131.508 (18)C22—C231.529 (13)
C12—H121.000C22—H221.000
C13—O131.39 (2)C23—O231.40 (2)
C13—C141.529 (13)C23—C241.524 (14)
C13—H131.000C23—H231.000
C14—O141.40 (3)C24—O241.439 (16)
C14—C151.505 (13)C24—C251.535 (16)
C14—H141.000C24—H241.000
C15—O151.420 (18)C25—O251.450 (14)
C15—C161.498 (13)C25—C261.526 (15)
C15—H151.000C25—H251.000
C16—O161.43 (2)C26—O261.41 (2)
C16—H16A1.000C26—H26A1.000
C16—H16B1.000C26—H26B1.000
O11—C14'1.423 (10)O21—C24'1.42 (3)
O12—HO120.983O22—HO220.986
O13—HO130.988O23—HO230.988
O14—HO140.972O24—HO240.980
O16—HO160.982O26—HO260.981
C11'—O11'1.409 (16)C21'—O21'1.44 (2)
C11'—O15'1.440 (15)C21'—O25'1.445 (15)
C11'—C12'1.521 (15)C21'—C22'1.537 (16)
C11'—H11'1.000C21'—H21'1.000
C12'—O12'1.428 (19)C22'—O22'1.421 (13)
C12'—C13'1.551 (14)C22'—C23'1.516 (19)
C12'—H12'1.000C22'—H22'1.000
C13'—O13'1.42 (3)C23'—O23'1.45 (2)
C13'—C14'1.530 (13)C23'—C24'1.543 (12)
C13'—H13'1.000C23'—H23'1.000
C14'—C15'1.508 (16)C24'—C25'1.565 (18)
C14'—H14'1.000C24'—H24'1.000
C15'—O15'1.44 (2)C25'—O25'1.41 (2)
C15'—C16'1.486 (16)C25'—C26'1.528 (19)
C15'—H15'1.000C25'—H25'1.001
C16'—O16'1.43 (3)C26'—O26'1.45 (2)
C16'—H16A'1.000C26'—H26A'0.999
C16'—H16B'0.999C26'—H26B'0.999
O11'—HO11'0.976O21'—HO21'0.983
O12'—HO12'0.977O22'—HO22'0.986
O13'—HO13'0.985O23'—HO23'0.979
O16'—HO16'0.984O26'—HO26'0.978
O15—C11—O11102.2 (9)O21—C21—O25111.9 (10)
O15—C11—C12104.5 (10)O21—C21—C22114.4 (9)
O11—C11—C12109.7 (8)O25—C21—C22111.9 (10)
O15—C11—H11112.5O21—C21—H21105.2
O11—C11—H11113.4O25—C21—H21107.0
C12—C11—H11113.6C22—C21—H21106.3
O12—C12—C13105.0 (10)O22—C22—C23104.3 (12)
O12—C12—C11113.3 (10)O22—C22—C21116.9 (10)
C13—C12—C11107.6 (9)C23—C22—C21104.5 (8)
O12—C12—H12111.3O22—C22—H22110.6
C13—C12—H12109.4C23—C22—H22110.0
C11—C12—H12110.0C21—C22—H22110.0
O13—C13—C12109.1 (12)O23—C23—C22106.8 (12)
O13—C13—C14111.2 (10)O23—C23—C24112.1 (11)
C12—C13—C14113.4 (9)C22—C23—C24113.2 (9)
O13—C13—H13108.5O23—C23—H23106.9
C12—C13—H13108.1C22—C23—H23108.8
C14—C13—H13106.3C24—C23—H23108.9
O14—C14—C15108.5 (12)O24—C24—C23111.2 (10)
O14—C14—C13111.3 (12)O24—C24—C25111.6 (10)
C15—C14—C13112.0 (8)C23—C24—C25110.1 (8)
O14—C14—H14107.2O24—C24—H24108.2
C15—C14—H14108.6C23—C24—H24108.3
C13—C14—H14109.1C25—C24—H24107.3
O15—C15—C16101.3 (10)O25—C25—C26113.8 (9)
O15—C15—C14111.1 (11)O25—C25—C24107.1 (10)
C16—C15—C14111.0 (9)C26—C25—C24113.4 (9)
O15—C15—H15111.7O25—C25—H25108.2
C16—C15—H15110.9C26—C25—H25106.7
C14—C15—H15110.6C24—C25—H25107.5
O16—C16—C15102.5 (12)O26—C26—C25110.1 (13)
O16—C16—H16A115.8O26—C26—H26A109.8
C15—C16—H16A111.6C25—C26—H26A110.5
O16—C16—H16B108.6O26—C26—H26B108.3
C15—C16—H16B111.5C25—C26—H26B111.2
H16A—C16—H16B107.0H26A—C26—H26B107.0
C11—O11—C14'120.2 (6)C24'—O21—C21115.3 (11)
C12—O12—HO12111.0C22—O22—HO22106.2
C13—O13—HO13109.6C23—O23—HO23105.7
C14—O14—HO14105.9C24—O24—HO24103.7
C15—O15—C11114.2 (12)C25—O25—C21111.8 (10)
C16—O16—HO16111.0C26—O26—HO26113.2
O11'—C11'—O15'110.2 (14)O21'—C21'—O25'105.6 (12)
O11'—C11'—C12'100.6 (12)O21'—C21'—C22'109.7 (10)
O15'—C11'—C12'113.5 (11)O25'—C21'—C22'108.3 (10)
O11'—C11'—H11'108.6O21'—C21'—H21'111.5
O15'—C11'—H11'110.9O25'—C21'—H21'111.0
C12'—C11'—H11'112.5C22'—C21'—H21'109.9
O12'—C12'—C11'102.8 (11)O22'—C22'—C23'110.5 (10)
O12'—C12'—C13'109.9 (11)O22'—C22'—C21'116.2 (10)
C11'—C12'—C13'111.1 (8)C23'—C22'—C21'109.6 (10)
O12'—C12'—H12'110.7O22'—C22'—H22'108.3
C11'—C12'—H12'108.7C23'—C22'—H22'106.7
C13'—C12'—H12'113.2C21'—C22'—H22'105.0
O13'—C13'—C14'112.5 (14)O23'—C23'—C22'109.3 (13)
O13'—C13'—C12'110.4 (12)O23'—C23'—C24'118.3 (13)
C14'—C13'—C12'110.3 (8)C22'—C23'—C24'108.3 (9)
O13'—C13'—H13'105.0O23'—C23'—H23'106.3
C14'—C13'—H13'109.0C22'—C23'—H23'106.9
C12'—C13'—H13'109.4C24'—C23'—H23'107.1
O11—C14'—C15'108.5 (7)O21—C24'—C23'102.2 (11)
O11—C14'—C13'115.5 (8)O21—C24'—C25'109.4 (10)
C15'—C14'—C13'105.6 (8)C23'—C24'—C25'113.7 (9)
O11—C14'—H14'109.6O21—C24'—H24'110.6
C15'—C14'—H14'107.3C23'—C24'—H24'110.9
C13'—C14'—H14'109.9C25'—C24'—H24'109.7
O15'—C15'—C16'107.3 (11)O25'—C25'—C26'107.2 (11)
O15'—C15'—C14'106.8 (10)O25'—C25'—C24'113.7 (13)
C16'—C15'—C14'113.1 (11)C26'—C25'—C24'123.7 (11)
O15'—C15'—H15'108.8O25'—C25'—H25'103.9
C16'—C15'—H15'110.6C26'—C25'—H25'102.6
C14'—C15'—H15'111.0C24'—C25'—H25'103.1
O16'—C16'—C15'103.3 (15)O26'—C26'—C25'111.4 (15)
O16'—C16'—H16A'112.9O26'—C26'—H26A'111.5
C15'—C16'—H16A'112.4C25'—C26'—H26A'108.4
O16'—C16'—H16B'110.7O26'—C26'—H26B'108.2
C15'—C16'—H16B'110.6C25'—C26'—H26B'110.2
H16A'—C16'—H16B'107.0H26A'—C26'—H26B'107.1
C11'—O11'—HO11'102.6C21'—O21'—HO21'107.2
C12'—O12'—HO12'108.8C22'—O22'—HO22'106.4
C13'—O13'—HO13'108.8C23'—O23'—HO23'111.7
C11'—O15'—C15'114.8 (12)C25'—O25'—C21'113.4 (13)
C16'—O16'—HO16'108.9C26'—O26'—HO26'107.3
O15—C11—C12—O12179.6 (12)O21—C21—C22—O2259.4 (18)
O11—C11—C12—O1271.4 (12)O25—C21—C22—O22172.5 (14)
O15—C11—C12—C1364.0 (12)O21—C21—C22—C23174.0 (12)
O11—C11—C12—C13173.0 (8)O25—C21—C22—C2357.8 (14)
O12—C12—C13—O1361.1 (15)O22—C22—C23—O2358.2 (16)
C11—C12—C13—O13178.0 (12)C21—C22—C23—O23178.5 (13)
O12—C12—C13—C14174.3 (11)O22—C22—C23—C24177.9 (12)
C11—C12—C13—C1453.4 (13)C21—C22—C23—C2454.7 (12)
O13—C13—C14—O1445.0 (17)O23—C23—C24—O2454.0 (18)
C12—C13—C14—O1478.4 (15)C22—C23—C24—O2466.8 (15)
O13—C13—C14—C15166.6 (12)O23—C23—C24—C25178.2 (13)
C12—C13—C14—C1543.2 (14)C22—C23—C24—C2557.4 (13)
O14—C14—C15—O1579.8 (15)O24—C24—C25—O2566.4 (16)
C13—C14—C15—O1543.4 (14)C23—C24—C25—O2557.6 (14)
O14—C14—C15—C1632.1 (15)O24—C24—C25—C2659.9 (16)
C13—C14—C15—C16155.3 (10)C23—C24—C25—C26176.1 (11)
O15—C15—C16—O1652.5 (14)O25—C25—C26—O266.0 (19)
C14—C15—C16—O16170.5 (13)C24—C25—C26—O26128.7 (15)
O15—C11—O11—C14'90.4 (10)O25—C21—O21—C24'91.1 (17)
C12—C11—O11—C14'159.1 (8)C22—C21—O21—C24'141.0 (13)
C16—C15—O15—C11178.8 (11)C26—C25—O25—C21170.9 (13)
C14—C15—O15—C1160.9 (15)C24—C25—O25—C2163.1 (15)
O11—C11—O15—C15175.0 (10)O21—C21—O25—C25164.5 (14)
C12—C11—O15—C1570.7 (14)C22—C21—O25—C2566.1 (16)
O11'—C11'—C12'—O12'41.5 (16)O21'—C21'—C22'—O22'54.1 (17)
O15'—C11'—C12'—O12'159.2 (14)O25'—C21'—C22'—O22'169.4 (14)
O11'—C11'—C12'—C13'76.0 (15)O21'—C21'—C22'—C23'179.7 (12)
O15'—C11'—C12'—C13'41.7 (15)O25'—C21'—C22'—C23'64.4 (14)
O12'—C12'—C13'—O13'72.9 (19)O22'—C22'—C23'—O23'43.7 (18)
C11'—C12'—C13'—O13'174.0 (16)C21'—C22'—C23'—O23'173.1 (14)
O12'—C12'—C13'—C14'162.1 (12)O22'—C22'—C23'—C24'173.9 (12)
C11'—C12'—C13'—C14'49.0 (13)C21'—C22'—C23'—C24'56.7 (12)
C11—O11—C14'—C15'145.0 (8)C21—O21—C24'—C23'102.1 (15)
C11—O11—C14'—C13'96.6 (10)C21—O21—C24'—C25'137.1 (14)
O13'—C13'—C14'—O1153.9 (19)O23'—C23'—C24'—O2170.1 (18)
C12'—C13'—C14'—O11177.7 (9)C22'—C23'—C24'—O21164.9 (12)
O13'—C13'—C14'—C15'173.9 (17)O23'—C23'—C24'—C25'172.1 (15)
C12'—C13'—C14'—C15'62.4 (12)C22'—C23'—C24'—C25'47.1 (13)
O11—C14'—C15'—O15'167.1 (12)O21—C24'—C25'—O25'158.1 (14)
C13'—C14'—C15'—O15'68.5 (14)C23'—C24'—C25'—O25'44.5 (16)
O11—C14'—C15'—C16'49.3 (16)O21—C24'—C25'—C26'69.0 (18)
C13'—C14'—C15'—C16'173.7 (14)C23'—C24'—C25'—C26'177.4 (14)
O15'—C15'—C16'—O16'91 (2)O25'—C25'—C26'—O26'55 (2)
C14'—C15'—C16'—O16'151.0 (16)C24'—C25'—C26'—O26'169.5 (14)
O11'—C11'—O15'—C15'61 (2)C26'—C25'—O25'—C21'168.6 (14)
C12'—C11'—O15'—C15'51 (2)C24'—C25'—O25'—C21'51.0 (18)
C16'—C15'—O15'—C11'173.7 (17)O21'—C21'—O25'—C25'178.5 (14)
C14'—C15'—O15'—C11'64.8 (18)C22'—C21'—O25'—C25'61.0 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—HO12···O13i0.9831.92 (4)2.86 (4)159.9 (16)
O13—HO13···O16ii0.9882.07 (3)2.96 (4)149 (2)
O14—HO14···O25iii0.9721.99 (3)2.60 (3)118.5 (19)
O16—HO16···O130.9821.78 (3)2.68 (3)150 (3)
O11—HO11···O23iv0.9762.74 (4)3.00 (4)96 (2)
O12—HO12···O12v0.9772.18 (3)2.55 (3)101.3 (18)
O13—HO13···O12v0.9852.74 (4)2.86 (4)87 (3)
O16—HO16···O12ii0.9841.82 (4)2.48 (4)121 (2)
O22—HO22···O23vi0.9861.97 (4)2.83 (4)144 (2)
O23—HO23···O26vi0.9882.04 (4)2.84 (4)137 (2)
O24—HO24···O15vii0.9812.46 (3)2.97 (3)111 (2)
O26—HO26···O22i0.9811.86 (3)2.54 (3)124 (2)
O21—HO21···O14viii0.9832.82 (3)3.02 (3)91.7 (19)
O22—HO22···O26ii0.9862.35 (3)3.09 (3)131.2 (16)
O23—HO23···O250.9791.97 (3)2.81 (3)143 (2)
O26—HO26···O22v0.9781.91 (3)2.52 (3)117.5 (19)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z; (iii) x, y, z+1; (iv) x, y1, z1; (v) x1, y, z1; (vi) x1, y, z; (vii) x, y+1, z+1; (viii) x, y, z1.

Experimental details

Crystal data
Chemical formulaC12H22O11
Mr342.30
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)7.6258 (4), 19.6559 (10), 5.0613 (3)
α, β, γ (°)95.646 (2), 105.430 (2), 80.996 (2)
V3)721.00 (7)
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 = 2.469, Rwp = 3.372, Rexp = 2.294, RBragg = 3.044, χ2 = NOT FOUND
No. of data points3946
No. of parameters182
No. of restraints124

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

Selected geometric parameters (Å, º) top
C11—O151.413 (17)C21—O211.438 (14)
C11—O111.418 (11)C21—O251.455 (19)
C11—C121.540 (14)C21—C221.559 (15)
C12—O121.401 (17)C22—O221.429 (19)
C12—C131.508 (18)C22—C231.529 (13)
C13—O131.39 (2)C23—O231.40 (2)
C13—C141.529 (13)C23—C241.524 (14)
C14—O141.40 (3)C24—O241.439 (16)
C14—C151.505 (13)C24—C251.535 (16)
C15—O151.420 (18)C25—O251.450 (14)
C15—C161.498 (13)C25—C261.526 (15)
C16—O161.43 (2)C26—O261.41 (2)
O11—C14'1.423 (10)O21—C24'1.42 (3)
C11'—O11'1.409 (16)C21'—O21'1.44 (2)
C11'—O15'1.440 (15)C21'—O25'1.445 (15)
C11'—C12'1.521 (15)C21'—C22'1.537 (16)
C12'—O12'1.428 (19)C22'—O22'1.421 (13)
C12'—C13'1.551 (14)C22'—C23'1.516 (19)
C13'—O13'1.42 (3)C23'—O23'1.45 (2)
C13'—C14'1.530 (13)C23'—C24'1.543 (12)
C14'—C15'1.508 (16)C24'—C25'1.565 (18)
C15'—O15'1.44 (2)C25'—O25'1.41 (2)
C15'—C16'1.486 (16)C25'—C26'1.528 (19)
C16'—O16'1.43 (3)C26'—O26'1.45 (2)
O15—C11—O11102.2 (9)O21—C21—O25111.9 (10)
O15—C11—C12104.5 (10)O21—C21—C22114.4 (9)
O11—C11—C12109.7 (8)O25—C21—C22111.9 (10)
O12—C12—C13105.0 (10)O22—C22—C23104.3 (12)
O12—C12—C11113.3 (10)O22—C22—C21116.9 (10)
C13—C12—C11107.6 (9)C23—C22—C21104.5 (8)
O13—C13—C12109.1 (12)O23—C23—C22106.8 (12)
O13—C13—C14111.2 (10)O23—C23—C24112.1 (11)
C12—C13—C14113.4 (9)C22—C23—C24113.2 (9)
O14—C14—C15108.5 (12)O24—C24—C23111.2 (10)
O14—C14—C13111.3 (12)O24—C24—C25111.6 (10)
C15—C14—C13112.0 (8)C23—C24—C25110.1 (8)
O15—C15—C16101.3 (10)O25—C25—C26113.8 (9)
O15—C15—C14111.1 (11)O25—C25—C24107.1 (10)
C16—C15—C14111.0 (9)C26—C25—C24113.4 (9)
O16—C16—C15102.5 (12)O26—C26—C25110.1 (13)
C11—O11—C14'120.2 (6)C24'—O21—C21115.3 (11)
C15—O15—C11114.2 (12)C25—O25—C21111.8 (10)
O11'—C11'—O15'110.2 (14)O21'—C21'—O25'105.6 (12)
O11'—C11'—C12'100.6 (12)O21'—C21'—C22'109.7 (10)
O15'—C11'—C12'113.5 (11)O25'—C21'—C22'108.3 (10)
O12'—C12'—C11'102.8 (11)O22'—C22'—C23'110.5 (10)
O12'—C12'—C13'109.9 (11)O22'—C22'—C21'116.2 (10)
C11'—C12'—C13'111.1 (8)C23'—C22'—C21'109.6 (10)
O13'—C13'—C14'112.5 (14)O23'—C23'—C22'109.3 (13)
O13'—C13'—C12'110.4 (12)O23'—C23'—C24'118.3 (13)
C14'—C13'—C12'110.3 (8)C22'—C23'—C24'108.3 (9)
O11—C14'—C15'108.5 (7)O21—C24'—C23'102.2 (11)
O11—C14'—C13'115.5 (8)O21—C24'—C25'109.4 (10)
C15'—C14'—C13'105.6 (8)C23'—C24'—C25'113.7 (9)
O15'—C15'—C16'107.3 (11)O25'—C25'—C26'107.2 (11)
O15'—C15'—C14'106.8 (10)O25'—C25'—C24'113.7 (13)
C16'—C15'—C14'113.1 (11)C26'—C25'—C24'123.7 (11)
O16'—C16'—C15'103.3 (15)O26'—C26'—C25'111.4 (15)
C11'—O15'—C15'114.8 (12)C25'—O25'—C21'113.4 (13)
O15—C11—C12—O12179.6 (12)O21—C21—C22—O2259.4 (18)
O11—C11—C12—O1271.4 (12)O25—C21—C22—O22172.5 (14)
O15—C11—C12—C1364.0 (12)O21—C21—C22—C23174.0 (12)
O11—C11—C12—C13173.0 (8)O25—C21—C22—C2357.8 (14)
O12—C12—C13—O1361.1 (15)O22—C22—C23—O2358.2 (16)
C11—C12—C13—O13178.0 (12)C21—C22—C23—O23178.5 (13)
O12—C12—C13—C14174.3 (11)O22—C22—C23—C24177.9 (12)
C11—C12—C13—C1453.4 (13)C21—C22—C23—C2454.7 (12)
O13—C13—C14—O1445.0 (17)O23—C23—C24—O2454.0 (18)
C12—C13—C14—O1478.4 (15)C22—C23—C24—O2466.8 (15)
O13—C13—C14—C15166.6 (12)O23—C23—C24—C25178.2 (13)
C12—C13—C14—C1543.2 (14)C22—C23—C24—C2557.4 (13)
O14—C14—C15—O1579.8 (15)O24—C24—C25—O2566.4 (16)
C13—C14—C15—O1543.4 (14)C23—C24—C25—O2557.6 (14)
O14—C14—C15—C1632.1 (15)O24—C24—C25—C2659.9 (16)
C13—C14—C15—C16155.3 (10)C23—C24—C25—C26176.1 (11)
O15—C15—C16—O1652.5 (14)O25—C25—C26—O266.0 (19)
C14—C15—C16—O16170.5 (13)C24—C25—C26—O26128.7 (15)
O15—C11—O11—C14'90.4 (10)O25—C21—O21—C24'91.1 (17)
C12—C11—O11—C14'159.1 (8)C22—C21—O21—C24'141.0 (13)
C16—C15—O15—C11178.8 (11)C26—C25—O25—C21170.9 (13)
C14—C15—O15—C1160.9 (15)C24—C25—O25—C2163.1 (15)
O11—C11—O15—C15175.0 (10)O21—C21—O25—C25164.5 (14)
C12—C11—O15—C1570.7 (14)C22—C21—O25—C2566.1 (16)
O11'—C11'—C12'—O12'41.5 (16)O21'—C21'—C22'—O22'54.1 (17)
O15'—C11'—C12'—O12'159.2 (14)O25'—C21'—C22'—O22'169.4 (14)
O11'—C11'—C12'—C13'76.0 (15)O21'—C21'—C22'—C23'179.7 (12)
O15'—C11'—C12'—C13'41.7 (15)O25'—C21'—C22'—C23'64.4 (14)
O12'—C12'—C13'—O13'72.9 (19)O22'—C22'—C23'—O23'43.7 (18)
C11'—C12'—C13'—O13'174.0 (16)C21'—C22'—C23'—O23'173.1 (14)
O12'—C12'—C13'—C14'162.1 (12)O22'—C22'—C23'—C24'173.9 (12)
C11'—C12'—C13'—C14'49.0 (13)C21'—C22'—C23'—C24'56.7 (12)
C11—O11—C14'—C15'145.0 (8)C21—O21—C24'—C23'102.1 (15)
C11—O11—C14'—C13'96.6 (10)C21—O21—C24'—C25'137.1 (14)
O13'—C13'—C14'—O1153.9 (19)O23'—C23'—C24'—O2170.1 (18)
C12'—C13'—C14'—O11177.7 (9)C22'—C23'—C24'—O21164.9 (12)
O13'—C13'—C14'—C15'173.9 (17)O23'—C23'—C24'—C25'172.1 (15)
C12'—C13'—C14'—C15'62.4 (12)C22'—C23'—C24'—C25'47.1 (13)
O11—C14'—C15'—O15'167.1 (12)O21—C24'—C25'—O25'158.1 (14)
C13'—C14'—C15'—O15'68.5 (14)C23'—C24'—C25'—O25'44.5 (16)
O11—C14'—C15'—C16'49.3 (16)O21—C24'—C25'—C26'69.0 (18)
C13'—C14'—C15'—C16'173.7 (14)C23'—C24'—C25'—C26'177.4 (14)
O15'—C15'—C16'—O16'91 (2)O25'—C25'—C26'—O26'55 (2)
C14'—C15'—C16'—O16'151.0 (16)C24'—C25'—C26'—O26'169.5 (14)
O11'—C11'—O15'—C15'61 (2)C26'—C25'—O25'—C21'168.6 (14)
C12'—C11'—O15'—C15'51 (2)C24'—C25'—O25'—C21'51.0 (18)
C16'—C15'—O15'—C11'173.7 (17)O21'—C21'—O25'—C25'178.5 (14)
C14'—C15'—O15'—C11'64.8 (18)C22'—C21'—O25'—C25'61.0 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—HO12···O13'i0.9831.92 (4)2.86 (4)159.9 (16)
O13—HO13···O16ii0.9882.07 (3)2.96 (4)148.5 (21)
O14—HO14···O25'iii0.9721.99 (3)2.60 (3)118.5 (19)
O16—HO16···O13'0.9821.78 (3)2.68 (3)149.9 (26)
O11'—HO11'···O23iv0.9762.74 (4)3.00 (4)95.6 (21)
O12'—HO12'···O12v0.9772.18 (3)2.55 (3)101.3 (18)
O13'—HO13'···O12v0.9852.74 (4)2.86 (4)87 (3)
O16'—HO16'···O12'ii0.9841.82 (4)2.48 (4)121.0 (24)
O22—HO22···O23'vi0.9861.97 (4)2.83 (4)144.1 (21)
O23—HO23···O26vi0.9882.04 (4)2.84 (4)136.6 (21)
O24—HO24···O15'vii0.9812.46 (3)2.97 (3)111 (2)
O26—HO26···O22i0.9811.86 (3)2.54 (3)124.4 (23)
O21'—HO21'···O14viii0.9832.82 (3)3.02 (3)91.7 (19)
O22'—HO22'···O26'ii0.9862.35 (3)3.09 (3)131.2 (16)
O23'—HO23'···O250.9791.97 (3)2.81 (3)142.5 (23)
O26'—HO26'···O22v0.9781.91 (3)2.52 (3)117.5 (19)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z; (iii) x, y, z+1; (iv) x, y1, z1; (v) x1, y, z1; (vi) x1, y, z; (vii) x, y+1, z+1; (viii) x, y, z1.
 

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