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
CCDC reference: 280364
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.
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.
4-
O-beta-
D-galactopyranosyl-
D-glucopyranose
top
Crystal data top
C12H22O11 | β = 105.430 (2)° |
Mr = 342.30 | γ = 80.996 (2)° |
Triclinic, P1 | V = 721.00 (7) Å3 |
Hall symbol: P 1 | Z = 2 |
a = 7.6258 (4) Å | Cu Kα radiation, λ = 1.540560 Å |
b = 19.6559 (10) Å | T = 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 tube | Scan method: Stationary detector |
Refinement top
Rp = 2.469 | Profile function: pseudo-Voigt |
Rwp = 3.372 | 182 parameters |
Rexp = 2.294 | 124 restraints |
RBragg = 3.044 | |
χ2 = NOT FOUND | Background function: linear interpolation between 24 points |
3946 data points | Preferred 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
C12H22O11 | β = 105.430 (2)° |
Mr = 342.30 | γ = 80.996 (2)° |
Triclinic, P1 | V = 721.00 (7) Å3 |
a = 7.6258 (4) Å | Z = 2 |
b = 19.6559 (10) Å | Cu Kα radiation, λ = 1.540560 Å |
c = 5.0613 (3) Å | T = 295 K |
α = 95.646 (2)° | ?, ? × ? × ? mm |
Data collection top
Enraf Nonius FR 590 diffractometer | Scan method: Stationary detector |
Refinement top
Rp = 2.469 | χ2 = NOT FOUND |
Rwp = 3.372 | 3946 data points |
Rexp = 2.294 | 182 parameters |
RBragg = 3.044 | 124 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C11 | 0.5276 (12) | 0.0439 (5) | 0.743 (3) | 0.030 (4)* | |
C12 | 0.7042 (11) | 0.0766 (5) | 0.781 (3) | 0.030 (4)* | |
C13 | 0.7147 (12) | 0.1294 (6) | 1.020 (3) | 0.030 (4)* | |
C14 | 0.5416 (11) | 0.1821 (5) | 0.992 (3) | 0.030 (4)* | |
C15 | 0.3692 (12) | 0.1488 (5) | 0.890 (3) | 0.030 (4)* | |
C16 | 0.2116 (15) | 0.1994 (5) | 0.750 (5) | 0.030 (4)* | |
O11 | 0.50000 | 0.00000 | 0.50000 | 0.030 (4)* | |
O12 | 0.865 (2) | 0.0296 (9) | 0.856 (5) | 0.030 (4)* | |
O13 | 0.870 (2) | 0.1617 (10) | 1.055 (5) | 0.030 (4)* | |
O14 | 0.537 (3) | 0.2325 (9) | 0.814 (4) | 0.030 (4)* | |
O15 | 0.384 (2) | 0.0989 (8) | 0.671 (3) | 0.030 (4)* | |
O16 | 0.073 (3) | 0.1562 (12) | 0.628 (5) | 0.030 (4)* | |
H11 | 0.5226 (12) | 0.0211 (5) | 0.908 (3) | 0.030 (4)* | |
H12 | 0.6995 (11) | 0.0999 (5) | 0.612 (3) | 0.030 (4)* | |
H13 | 0.7276 (12) | 0.1047 (6) | 1.190 (3) | 0.030 (4)* | |
H14 | 0.5416 (11) | 0.2063 (5) | 1.176 (3) | 0.030 (4)* | |
H15 | 0.3396 (12) | 0.1285 (5) | 1.044 (3) | 0.030 (4)* | |
H16a | 0.2474 (15) | 0.2265 (5) | 0.620 (5) | 0.030 (4)* | |
H16b | 0.1664 (15) | 0.2334 (5) | 0.886 (5) | 0.030 (4)* | |
HO12 | 0.934 (2) | 0.0403 (9) | 1.045 (5) | 0.030 (4)* | |
HO13 | 0.891 (2) | 0.1665 (10) | 0.874 (5) | 0.030 (4)* | |
HO14 | 0.651 (3) | 0.2526 (9) | 0.887 (4) | 0.030 (4)* | |
HO16 | 0.127 (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)* | |
C21 | 0.5147 (12) | 0.5588 (5) | 0.563 (3) | 0.037 (5)* | |
C22 | 0.3304 (11) | 0.5882 (5) | 0.637 (3) | 0.037 (5)* | |
C23 | 0.3207 (11) | 0.6665 (5) | 0.637 (3) | 0.037 (5)* | |
C24 | 0.4896 (12) | 0.6942 (9) | 0.8248 (18) | 0.037 (5)* | |
C25 | 0.6633 (12) | 0.6591 (5) | 0.742 (3) | 0.037 (5)* | |
C26 | 0.8376 (15) | 0.6874 (6) | 0.909 (5) | 0.037 (5)* | |
O21 | 0.545 (3) | 0.4849 (5) | 0.525 (4) | 0.037 (5)* | |
O22 | 0.165 (2) | 0.5729 (12) | 0.444 (5) | 0.037 (5)* | |
O23 | 0.159 (2) | 0.6957 (12) | 0.710 (5) | 0.037 (5)* | |
O24 | 0.502 (3) | 0.6858 (11) | 1.109 (2) | 0.037 (5)* | |
O25 | 0.670 (2) | 0.5854 (5) | 0.758 (4) | 0.037 (5)* | |
O26 | 0.973 (2) | 0.6328 (9) | 1.017 (5) | 0.037 (5)* | |
H21 | 0.5062 (12) | 0.5763 (5) | 0.381 (3) | 0.037 (5)* | |
H22 | 0.3338 (11) | 0.5749 (5) | 0.824 (3) | 0.037 (5)* | |
H23 | 0.3071 (11) | 0.6792 (5) | 0.445 (3) | 0.037 (5)* | |
H24 | 0.4786 (12) | 0.7446 (9) | 0.7990 (18) | 0.037 (5)* | |
H25 | 0.6483 (12) | 0.6685 (5) | 0.547 (3) | 0.037 (5)* | |
H26a | 0.8110 (15) | 0.7204 (6) | 1.061 (5) | 0.037 (5)* | |
H26b | 0.8880 (15) | 0.7135 (6) | 0.792 (5) | 0.037 (5)* | |
HO22 | 0.135 (2) | 0.5307 (12) | 0.503 (5) | 0.037 (5)* | |
HO23 | 0.101 (2) | 0.6564 (12) | 0.739 (5) | 0.037 (5)* | |
HO24 | 0.421 (3) | 0.7258 (11) | 1.160 (2) | 0.037 (5)* | |
HO26 | 0.971 (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—O15 | 1.413 (17) | C21—O21 | 1.438 (14) |
C11—O11 | 1.418 (11) | C21—O25 | 1.455 (19) |
C11—C12 | 1.540 (14) | C21—C22 | 1.559 (15) |
C11—H11 | 1.000 | C21—H21 | 1.000 |
C12—O12 | 1.401 (17) | C22—O22 | 1.429 (19) |
C12—C13 | 1.508 (18) | C22—C23 | 1.529 (13) |
C12—H12 | 1.000 | C22—H22 | 1.000 |
C13—O13 | 1.39 (2) | C23—O23 | 1.40 (2) |
C13—C14 | 1.529 (13) | C23—C24 | 1.524 (14) |
C13—H13 | 1.000 | C23—H23 | 1.000 |
C14—O14 | 1.40 (3) | C24—O24 | 1.439 (16) |
C14—C15 | 1.505 (13) | C24—C25 | 1.535 (16) |
C14—H14 | 1.000 | C24—H24 | 1.000 |
C15—O15 | 1.420 (18) | C25—O25 | 1.450 (14) |
C15—C16 | 1.498 (13) | C25—C26 | 1.526 (15) |
C15—H15 | 1.000 | C25—H25 | 1.000 |
C16—O16 | 1.43 (2) | C26—O26 | 1.41 (2) |
C16—H16A | 1.000 | C26—H26A | 1.000 |
C16—H16B | 1.000 | C26—H26B | 1.000 |
O11—C14' | 1.423 (10) | O21—C24' | 1.42 (3) |
O12—HO12 | 0.983 | O22—HO22 | 0.986 |
O13—HO13 | 0.988 | O23—HO23 | 0.988 |
O14—HO14 | 0.972 | O24—HO24 | 0.980 |
O16—HO16 | 0.982 | O26—HO26 | 0.981 |
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' | 1.000 | C21'—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' | 1.000 | C22'—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' | 1.000 | C23'—H23' | 1.000 |
C14'—C15' | 1.508 (16) | C24'—C25' | 1.565 (18) |
C14'—H14' | 1.000 | C24'—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' | 1.000 | C25'—H25' | 1.001 |
C16'—O16' | 1.43 (3) | C26'—O26' | 1.45 (2) |
C16'—H16A' | 1.000 | C26'—H26A' | 0.999 |
C16'—H16B' | 0.999 | C26'—H26B' | 0.999 |
O11'—HO11' | 0.976 | O21'—HO21' | 0.983 |
O12'—HO12' | 0.977 | O22'—HO22' | 0.986 |
O13'—HO13' | 0.985 | O23'—HO23' | 0.979 |
O16'—HO16' | 0.984 | O26'—HO26' | 0.978 |
| | | |
O15—C11—O11 | 102.2 (9) | O21—C21—O25 | 111.9 (10) |
O15—C11—C12 | 104.5 (10) | O21—C21—C22 | 114.4 (9) |
O11—C11—C12 | 109.7 (8) | O25—C21—C22 | 111.9 (10) |
O15—C11—H11 | 112.5 | O21—C21—H21 | 105.2 |
O11—C11—H11 | 113.4 | O25—C21—H21 | 107.0 |
C12—C11—H11 | 113.6 | C22—C21—H21 | 106.3 |
O12—C12—C13 | 105.0 (10) | O22—C22—C23 | 104.3 (12) |
O12—C12—C11 | 113.3 (10) | O22—C22—C21 | 116.9 (10) |
C13—C12—C11 | 107.6 (9) | C23—C22—C21 | 104.5 (8) |
O12—C12—H12 | 111.3 | O22—C22—H22 | 110.6 |
C13—C12—H12 | 109.4 | C23—C22—H22 | 110.0 |
C11—C12—H12 | 110.0 | C21—C22—H22 | 110.0 |
O13—C13—C12 | 109.1 (12) | O23—C23—C22 | 106.8 (12) |
O13—C13—C14 | 111.2 (10) | O23—C23—C24 | 112.1 (11) |
C12—C13—C14 | 113.4 (9) | C22—C23—C24 | 113.2 (9) |
O13—C13—H13 | 108.5 | O23—C23—H23 | 106.9 |
C12—C13—H13 | 108.1 | C22—C23—H23 | 108.8 |
C14—C13—H13 | 106.3 | C24—C23—H23 | 108.9 |
O14—C14—C15 | 108.5 (12) | O24—C24—C23 | 111.2 (10) |
O14—C14—C13 | 111.3 (12) | O24—C24—C25 | 111.6 (10) |
C15—C14—C13 | 112.0 (8) | C23—C24—C25 | 110.1 (8) |
O14—C14—H14 | 107.2 | O24—C24—H24 | 108.2 |
C15—C14—H14 | 108.6 | C23—C24—H24 | 108.3 |
C13—C14—H14 | 109.1 | C25—C24—H24 | 107.3 |
O15—C15—C16 | 101.3 (10) | O25—C25—C26 | 113.8 (9) |
O15—C15—C14 | 111.1 (11) | O25—C25—C24 | 107.1 (10) |
C16—C15—C14 | 111.0 (9) | C26—C25—C24 | 113.4 (9) |
O15—C15—H15 | 111.7 | O25—C25—H25 | 108.2 |
C16—C15—H15 | 110.9 | C26—C25—H25 | 106.7 |
C14—C15—H15 | 110.6 | C24—C25—H25 | 107.5 |
O16—C16—C15 | 102.5 (12) | O26—C26—C25 | 110.1 (13) |
O16—C16—H16A | 115.8 | O26—C26—H26A | 109.8 |
C15—C16—H16A | 111.6 | C25—C26—H26A | 110.5 |
O16—C16—H16B | 108.6 | O26—C26—H26B | 108.3 |
C15—C16—H16B | 111.5 | C25—C26—H26B | 111.2 |
H16A—C16—H16B | 107.0 | H26A—C26—H26B | 107.0 |
C11—O11—C14' | 120.2 (6) | C24'—O21—C21 | 115.3 (11) |
C12—O12—HO12 | 111.0 | C22—O22—HO22 | 106.2 |
C13—O13—HO13 | 109.6 | C23—O23—HO23 | 105.7 |
C14—O14—HO14 | 105.9 | C24—O24—HO24 | 103.7 |
C15—O15—C11 | 114.2 (12) | C25—O25—C21 | 111.8 (10) |
C16—O16—HO16 | 111.0 | C26—O26—HO26 | 113.2 |
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' | 108.6 | O21'—C21'—H21' | 111.5 |
O15'—C11'—H11' | 110.9 | O25'—C21'—H21' | 111.0 |
C12'—C11'—H11' | 112.5 | C22'—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' | 110.7 | O22'—C22'—H22' | 108.3 |
C11'—C12'—H12' | 108.7 | C23'—C22'—H22' | 106.7 |
C13'—C12'—H12' | 113.2 | C21'—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' | 105.0 | O23'—C23'—H23' | 106.3 |
C14'—C13'—H13' | 109.0 | C22'—C23'—H23' | 106.9 |
C12'—C13'—H13' | 109.4 | C24'—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' | 109.6 | O21—C24'—H24' | 110.6 |
C15'—C14'—H14' | 107.3 | C23'—C24'—H24' | 110.9 |
C13'—C14'—H14' | 109.9 | C25'—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' | 108.8 | O25'—C25'—H25' | 103.9 |
C16'—C15'—H15' | 110.6 | C26'—C25'—H25' | 102.6 |
C14'—C15'—H15' | 111.0 | C24'—C25'—H25' | 103.1 |
O16'—C16'—C15' | 103.3 (15) | O26'—C26'—C25' | 111.4 (15) |
O16'—C16'—H16A' | 112.9 | O26'—C26'—H26A' | 111.5 |
C15'—C16'—H16A' | 112.4 | C25'—C26'—H26A' | 108.4 |
O16'—C16'—H16B' | 110.7 | O26'—C26'—H26B' | 108.2 |
C15'—C16'—H16B' | 110.6 | C25'—C26'—H26B' | 110.2 |
H16A'—C16'—H16B' | 107.0 | H26A'—C26'—H26B' | 107.1 |
C11'—O11'—HO11' | 102.6 | C21'—O21'—HO21' | 107.2 |
C12'—O12'—HO12' | 108.8 | C22'—O22'—HO22' | 106.4 |
C13'—O13'—HO13' | 108.8 | C23'—O23'—HO23' | 111.7 |
C11'—O15'—C15' | 114.8 (12) | C25'—O25'—C21' | 113.4 (13) |
C16'—O16'—HO16' | 108.9 | C26'—O26'—HO26' | 107.3 |
| | | |
O15—C11—C12—O12 | 179.6 (12) | O21—C21—C22—O22 | −59.4 (18) |
O11—C11—C12—O12 | −71.4 (12) | O25—C21—C22—O22 | 172.5 (14) |
O15—C11—C12—C13 | 64.0 (12) | O21—C21—C22—C23 | −174.0 (12) |
O11—C11—C12—C13 | 173.0 (8) | O25—C21—C22—C23 | 57.8 (14) |
O12—C12—C13—O13 | 61.1 (15) | O22—C22—C23—O23 | 58.2 (16) |
C11—C12—C13—O13 | −178.0 (12) | C21—C22—C23—O23 | −178.5 (13) |
O12—C12—C13—C14 | −174.3 (11) | O22—C22—C23—C24 | −177.9 (12) |
C11—C12—C13—C14 | −53.4 (13) | C21—C22—C23—C24 | −54.7 (12) |
O13—C13—C14—O14 | 45.0 (17) | O23—C23—C24—O24 | 54.0 (18) |
C12—C13—C14—O14 | −78.4 (15) | C22—C23—C24—O24 | −66.8 (15) |
O13—C13—C14—C15 | 166.6 (12) | O23—C23—C24—C25 | 178.2 (13) |
C12—C13—C14—C15 | 43.2 (14) | C22—C23—C24—C25 | 57.4 (13) |
O14—C14—C15—O15 | 79.8 (15) | O24—C24—C25—O25 | 66.4 (16) |
C13—C14—C15—O15 | −43.4 (14) | C23—C24—C25—O25 | −57.6 (14) |
O14—C14—C15—C16 | −32.1 (15) | O24—C24—C25—C26 | −59.9 (16) |
C13—C14—C15—C16 | −155.3 (10) | C23—C24—C25—C26 | 176.1 (11) |
O15—C15—C16—O16 | 52.5 (14) | O25—C25—C26—O26 | 6.0 (19) |
C14—C15—C16—O16 | 170.5 (13) | C24—C25—C26—O26 | 128.7 (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—C11 | 178.8 (11) | C26—C25—O25—C21 | −170.9 (13) |
C14—C15—O15—C11 | 60.9 (15) | C24—C25—O25—C21 | 63.1 (15) |
O11—C11—O15—C15 | 175.0 (10) | O21—C21—O25—C25 | 164.5 (14) |
C12—C11—O15—C15 | −70.7 (14) | C22—C21—O25—C25 | −66.1 (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'—O11 | −53.9 (19) | O23'—C23'—C24'—O21 | −70.1 (18) |
C12'—C13'—C14'—O11 | 177.7 (9) | C22'—C23'—C24'—O21 | 164.9 (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···A | D—H | H···A | D···A | D—H···A |
O12—HO12···O13′i | 0.983 | 1.92 (4) | 2.86 (4) | 159.9 (16) |
O13—HO13···O16ii | 0.988 | 2.07 (3) | 2.96 (4) | 149 (2) |
O14—HO14···O25′iii | 0.972 | 1.99 (3) | 2.60 (3) | 118.5 (19) |
O16—HO16···O13′ | 0.982 | 1.78 (3) | 2.68 (3) | 150 (3) |
O11′—HO11′···O23iv | 0.976 | 2.74 (4) | 3.00 (4) | 96 (2) |
O12′—HO12′···O12v | 0.977 | 2.18 (3) | 2.55 (3) | 101.3 (18) |
O13′—HO13′···O12v | 0.985 | 2.74 (4) | 2.86 (4) | 87 (3) |
O16′—HO16′···O12′ii | 0.984 | 1.82 (4) | 2.48 (4) | 121 (2) |
O22—HO22···O23′vi | 0.986 | 1.97 (4) | 2.83 (4) | 144 (2) |
O23—HO23···O26vi | 0.988 | 2.04 (4) | 2.84 (4) | 137 (2) |
O24—HO24···O15′vii | 0.981 | 2.46 (3) | 2.97 (3) | 111 (2) |
O26—HO26···O22i | 0.981 | 1.86 (3) | 2.54 (3) | 124 (2) |
O21′—HO21′···O14viii | 0.983 | 2.82 (3) | 3.02 (3) | 91.7 (19) |
O22′—HO22′···O26′ii | 0.986 | 2.35 (3) | 3.09 (3) | 131.2 (16) |
O23′—HO23′···O25 | 0.979 | 1.97 (3) | 2.81 (3) | 143 (2) |
O26′—HO26′···O22v | 0.978 | 1.91 (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, y−1, z−1; (v) x−1, y, z−1; (vi) x−1, y, z; (vii) x, y+1, z+1; (viii) x, y, z−1. |
Experimental details
Crystal data |
Chemical formula | C12H22O11 |
Mr | 342.30 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 721.00 (7) |
Z | 2 |
Radiation type | Cu Kα, λ = 1.540560 Å |
Specimen shape, size (mm) | ?, ? × ? × ? |
|
Data collection |
Diffractometer | Enraf Nonius FR 590 diffractometer |
Specimen mounting | ? |
Data collection mode | ? |
Scan method | Stationary detector |
2θ values (°) | 2θfixed = ? |
|
Refinement |
R factors and goodness of fit | Rp = 2.469, Rwp = 3.372, Rexp = 2.294, RBragg = 3.044, χ2 = NOT FOUND |
No. of data points | 3946 |
No. of parameters | 182 |
No. of restraints | 124 |
Selected geometric parameters (Å, º) topC11—O15 | 1.413 (17) | C21—O21 | 1.438 (14) |
C11—O11 | 1.418 (11) | C21—O25 | 1.455 (19) |
C11—C12 | 1.540 (14) | C21—C22 | 1.559 (15) |
C12—O12 | 1.401 (17) | C22—O22 | 1.429 (19) |
C12—C13 | 1.508 (18) | C22—C23 | 1.529 (13) |
C13—O13 | 1.39 (2) | C23—O23 | 1.40 (2) |
C13—C14 | 1.529 (13) | C23—C24 | 1.524 (14) |
C14—O14 | 1.40 (3) | C24—O24 | 1.439 (16) |
C14—C15 | 1.505 (13) | C24—C25 | 1.535 (16) |
C15—O15 | 1.420 (18) | C25—O25 | 1.450 (14) |
C15—C16 | 1.498 (13) | C25—C26 | 1.526 (15) |
C16—O16 | 1.43 (2) | C26—O26 | 1.41 (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—O11 | 102.2 (9) | O21—C21—O25 | 111.9 (10) |
O15—C11—C12 | 104.5 (10) | O21—C21—C22 | 114.4 (9) |
O11—C11—C12 | 109.7 (8) | O25—C21—C22 | 111.9 (10) |
O12—C12—C13 | 105.0 (10) | O22—C22—C23 | 104.3 (12) |
O12—C12—C11 | 113.3 (10) | O22—C22—C21 | 116.9 (10) |
C13—C12—C11 | 107.6 (9) | C23—C22—C21 | 104.5 (8) |
O13—C13—C12 | 109.1 (12) | O23—C23—C22 | 106.8 (12) |
O13—C13—C14 | 111.2 (10) | O23—C23—C24 | 112.1 (11) |
C12—C13—C14 | 113.4 (9) | C22—C23—C24 | 113.2 (9) |
O14—C14—C15 | 108.5 (12) | O24—C24—C23 | 111.2 (10) |
O14—C14—C13 | 111.3 (12) | O24—C24—C25 | 111.6 (10) |
C15—C14—C13 | 112.0 (8) | C23—C24—C25 | 110.1 (8) |
O15—C15—C16 | 101.3 (10) | O25—C25—C26 | 113.8 (9) |
O15—C15—C14 | 111.1 (11) | O25—C25—C24 | 107.1 (10) |
C16—C15—C14 | 111.0 (9) | C26—C25—C24 | 113.4 (9) |
O16—C16—C15 | 102.5 (12) | O26—C26—C25 | 110.1 (13) |
C11—O11—C14' | 120.2 (6) | C24'—O21—C21 | 115.3 (11) |
C15—O15—C11 | 114.2 (12) | C25—O25—C21 | 111.8 (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—O12 | 179.6 (12) | O21—C21—C22—O22 | −59.4 (18) |
O11—C11—C12—O12 | −71.4 (12) | O25—C21—C22—O22 | 172.5 (14) |
O15—C11—C12—C13 | 64.0 (12) | O21—C21—C22—C23 | −174.0 (12) |
O11—C11—C12—C13 | 173.0 (8) | O25—C21—C22—C23 | 57.8 (14) |
O12—C12—C13—O13 | 61.1 (15) | O22—C22—C23—O23 | 58.2 (16) |
C11—C12—C13—O13 | −178.0 (12) | C21—C22—C23—O23 | −178.5 (13) |
O12—C12—C13—C14 | −174.3 (11) | O22—C22—C23—C24 | −177.9 (12) |
C11—C12—C13—C14 | −53.4 (13) | C21—C22—C23—C24 | −54.7 (12) |
O13—C13—C14—O14 | 45.0 (17) | O23—C23—C24—O24 | 54.0 (18) |
C12—C13—C14—O14 | −78.4 (15) | C22—C23—C24—O24 | −66.8 (15) |
O13—C13—C14—C15 | 166.6 (12) | O23—C23—C24—C25 | 178.2 (13) |
C12—C13—C14—C15 | 43.2 (14) | C22—C23—C24—C25 | 57.4 (13) |
O14—C14—C15—O15 | 79.8 (15) | O24—C24—C25—O25 | 66.4 (16) |
C13—C14—C15—O15 | −43.4 (14) | C23—C24—C25—O25 | −57.6 (14) |
O14—C14—C15—C16 | −32.1 (15) | O24—C24—C25—C26 | −59.9 (16) |
C13—C14—C15—C16 | −155.3 (10) | C23—C24—C25—C26 | 176.1 (11) |
O15—C15—C16—O16 | 52.5 (14) | O25—C25—C26—O26 | 6.0 (19) |
C14—C15—C16—O16 | 170.5 (13) | C24—C25—C26—O26 | 128.7 (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—C11 | 178.8 (11) | C26—C25—O25—C21 | −170.9 (13) |
C14—C15—O15—C11 | 60.9 (15) | C24—C25—O25—C21 | 63.1 (15) |
O11—C11—O15—C15 | 175.0 (10) | O21—C21—O25—C25 | 164.5 (14) |
C12—C11—O15—C15 | −70.7 (14) | C22—C21—O25—C25 | −66.1 (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'—O11 | −53.9 (19) | O23'—C23'—C24'—O21 | −70.1 (18) |
C12'—C13'—C14'—O11 | 177.7 (9) | C22'—C23'—C24'—O21 | 164.9 (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···A | D—H | H···A | D···A | D—H···A |
O12—HO12···O13'i | 0.983 | 1.92 (4) | 2.86 (4) | 159.9 (16) |
O13—HO13···O16ii | 0.988 | 2.07 (3) | 2.96 (4) | 148.5 (21) |
O14—HO14···O25'iii | 0.972 | 1.99 (3) | 2.60 (3) | 118.5 (19) |
O16—HO16···O13' | 0.982 | 1.78 (3) | 2.68 (3) | 149.9 (26) |
O11'—HO11'···O23iv | 0.976 | 2.74 (4) | 3.00 (4) | 95.6 (21) |
O12'—HO12'···O12v | 0.977 | 2.18 (3) | 2.55 (3) | 101.3 (18) |
O13'—HO13'···O12v | 0.985 | 2.74 (4) | 2.86 (4) | 87 (3) |
O16'—HO16'···O12'ii | 0.984 | 1.82 (4) | 2.48 (4) | 121.0 (24) |
O22—HO22···O23'vi | 0.986 | 1.97 (4) | 2.83 (4) | 144.1 (21) |
O23—HO23···O26vi | 0.988 | 2.04 (4) | 2.84 (4) | 136.6 (21) |
O24—HO24···O15'vii | 0.981 | 2.46 (3) | 2.97 (3) | 111 (2) |
O26—HO26···O22i | 0.981 | 1.86 (3) | 2.54 (3) | 124.4 (23) |
O21'—HO21'···O14viii | 0.983 | 2.82 (3) | 3.02 (3) | 91.7 (19) |
O22'—HO22'···O26'ii | 0.986 | 2.35 (3) | 3.09 (3) | 131.2 (16) |
O23'—HO23'···O25 | 0.979 | 1.97 (3) | 2.81 (3) | 142.5 (23) |
O26'—HO26'···O22v | 0.978 | 1.91 (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, y−1, z−1; (v) x−1, y, z−1; (vi) x−1, y, z; (vii) x, y+1, z+1; (viii) x, y, z−1. |