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
CCDC reference: 268161
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.
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 = 106.2610 (7)° |
Mr = 342.30 | γ = 97.1529 (8)° |
Triclinic, P1 | V = 720.18 (3) Å3 |
Hall symbol: P 1 | Z = 2 |
a = 7.65217 (17) Å | Cu Kα radiation, λ = 1.540560 Å |
b = 19.8637 (5) Å | T = 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 tube | Scan method: Stationary detector |
Refinement top
Rp = 2.662 | Profile function: pseudo-Voigt |
Rwp = 3.511 | 195 parameters |
Rexp = 1.586 | 118 restraints |
RBragg = 1.607 | |
χ2 = NOT FOUND | Background function: linear interpolation between 30 points |
3946 data points | Preferred 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
C12H22O11 | β = 106.2610 (7)° |
Mr = 342.30 | γ = 97.1529 (8)° |
Triclinic, P1 | V = 720.18 (3) Å3 |
a = 7.65217 (17) Å | Z = 2 |
b = 19.8637 (5) Å | Cu Kα radiation, λ = 1.540560 Å |
c = 4.98773 (13) Å | T = 293 K |
α = 92.0279 (10)° | ?, ? × ? × ? mm |
Data collection top
Enraf Nonius FR 590 diffractometer | Scan method: Stationary detector |
Refinement top
Rp = 2.662 | χ2 = NOT FOUND |
Rwp = 3.511 | 3946 data points |
Rexp = 1.586 | 195 parameters |
RBragg = 1.607 | 118 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C11 | 0.4157 (11) | 0.5519 (4) | 0.824 (3) | 0.0174 (14)* | |
C12 | 0.2271 (11) | 0.5730 (4) | 0.811 (3) | 0.0174 (14)* | |
C13 | 0.2221 (11) | 0.6383 (4) | 0.663 (3) | 0.0174 (14)* | |
C14 | 0.3910 (11) | 0.6908 (6) | 0.783 (2) | 0.0174 (14)* | |
C15 | 0.5698 (11) | 0.6604 (4) | 0.844 (3) | 0.0174 (14)* | |
C16 | 0.7358 (12) | 0.7119 (6) | 0.978 (5) | 0.0174 (14)* | |
O11 | 0.4130 (16) | 0.4922 (5) | 0.971 (3) | 0.0174 (14)* | |
O12 | 0.0724 (14) | 0.5241 (6) | 0.666 (3) | 0.0174 (14)* | |
O13 | 0.0613 (15) | 0.6709 (7) | 0.624 (3) | 0.0174 (14)* | |
O14 | 0.3914 (18) | 0.7197 (7) | 1.047 (2) | 0.0174 (14)* | |
O15 | 0.5635 (16) | 0.5998 (4) | 0.985 (2) | 0.0174 (14)* | |
O16 | 0.8926 (15) | 0.6765 (7) | 1.034 (4) | 0.0174 (14)* | |
H11 | 0.4309 (11) | 0.5415 (4) | 0.635 (3) | 0.0174 (14)* | |
H12 | 0.2199 (11) | 0.5838 (4) | 1.005 (3) | 0.0174 (14)* | |
H13 | 0.2241 (11) | 0.6262 (4) | 0.467 (3) | 0.0174 (14)* | |
H14 | 0.3956 (11) | 0.7285 (6) | 0.657 (2) | 0.0174 (14)* | |
H15 | 0.5836 (11) | 0.6463 (4) | 0.657 (3) | 0.0174 (14)* | |
H16a | 0.7220 (12) | 0.7317 (6) | 1.157 (5) | 0.0174 (14)* | |
H16b | 0.7460 (12) | 0.7504 (6) | 0.857 (5) | 0.0174 (14)* | |
HO12 | −0.0047 (14) | 0.5145 (6) | 0.792 (3) | 0.0174 (14)* | |
HO13 | −0.0053 (15) | 0.6499 (7) | 0.750 (3) | 0.0174 (14)* | |
HO14 | 0.2961 (18) | 0.7501 (7) | 1.012 (2) | 0.0174 (14)* | |
HO16 | 0.9615 (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)* | |
C21 | 0.4100 (11) | 0.0719 (4) | 0.593 (3) | 0.0149 (15)* | |
C22 | 0.5985 (10) | 0.1012 (4) | 0.568 (3) | 0.0149 (15)* | |
C23 | 0.6131 (11) | 0.1781 (4) | 0.593 (4) | 0.0149 (15)* | |
C24 | 0.4474 (11) | 0.2071 (7) | 0.4090 (19) | 0.0149 (15)* | |
C25 | 0.2664 (11) | 0.1668 (4) | 0.410 (3) | 0.0149 (15)* | |
C26 | 0.0976 (12) | 0.1913 (7) | 0.220 (4) | 0.0149 (15)* | |
O21 | 0.39795 | 0.00068 | 0.58876 | 0.0149 (15)* | |
O22 | 0.7538 (17) | 0.0781 (7) | 0.760 (3) | 0.0149 (15)* | |
O23 | 0.7820 (13) | 0.2143 (7) | 0.579 (3) | 0.0149 (15)* | |
O24 | 0.4561 (19) | 0.2065 (7) | 0.1281 (18) | 0.0149 (15)* | |
O25 | 0.2659 (18) | 0.0943 (4) | 0.380 (3) | 0.0149 (15)* | |
O26 | −0.0442 (16) | 0.1411 (6) | 0.260 (4) | 0.0149 (15)* | |
H21 | 0.4024 (11) | 0.0891 (4) | 0.780 (3) | 0.0149 (15)* | |
H22 | 0.6013 (10) | 0.0863 (4) | 0.375 (3) | 0.0149 (15)* | |
H23 | 0.6107 (11) | 0.1892 (4) | 0.789 (4) | 0.0149 (15)* | |
H24 | 0.4527 (11) | 0.2549 (7) | 0.4840 (19) | 0.0149 (15)* | |
H25 | 0.2560 (11) | 0.1767 (4) | 0.603 (3) | 0.0149 (15)* | |
H26a | 0.1038 (12) | 0.1897 (7) | 0.022 (4) | 0.0149 (15)* | |
H26b | 0.0824 (12) | 0.2390 (7) | 0.271 (4) | 0.0149 (15)* | |
HO22 | 0.8236 (17) | 0.0520 (7) | 0.667 (3) | 0.0149 (15)* | |
HO23 | 0.8468 (13) | 0.1843 (7) | 0.492 (3) | 0.0149 (15)* | |
HO24 | 0.5764 (19) | 0.2071 (7) | 0.0933 (18) | 0.0149 (15)* | |
HO26 | −0.1475 (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—O15 | 1.415 (12) | C21—O21 | 1.406 (9) |
C11—O11 | 1.416 (15) | C21—O25 | 1.430 (16) |
C11—C12 | 1.538 (13) | C21—C22 | 1.527 (14) |
C11—H11 | 1.000 | C21—H21 | 1.000 |
C12—O12 | 1.434 (13) | C22—O22 | 1.439 (16) |
C12—C13 | 1.516 (15) | C22—C23 | 1.515 (12) |
C12—H12 | 1.000 | C22—H22 | 1.000 |
C13—O13 | 1.430 (15) | C23—O23 | 1.420 (15) |
C13—C14 | 1.518 (12) | C23—C24 | 1.533 (14) |
C13—H13 | 1.000 | C23—H23 | 1.000 |
C14—O14 | 1.415 (16) | C24—O24 | 1.420 (14) |
C14—C15 | 1.521 (13) | C24—C25 | 1.512 (13) |
C14—H14 | 1.001 | C24—H24 | 1.000 |
C15—O15 | 1.419 (15) | C25—O25 | 1.441 (12) |
C15—C16 | 1.503 (12) | C25—C26 | 1.520 (15) |
C15—H15 | 1.000 | C25—H25 | 1.000 |
C16—O16 | 1.431 (17) | C26—O26 | 1.442 (18) |
C16—H16A | 1.001 | C26—H26A | 1.000 |
C16—H16B | 1.000 | C26—H26B | 1.000 |
O11—C14' | 1.426 (15) | O21—C24' | 1.414 (12) |
O12—HO12 | 0.985 | O22—HO22 | 0.980 |
O13—HO13 | 0.986 | O23—HO23 | 0.982 |
O14—HO14 | 0.986 | O24—HO24 | 0.982 |
O16—HO16 | 0.986 | O26—HO26 | 0.938 |
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' | 1.000 | C21'—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' | 1.000 | C22'—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' | 1.000 | C23'—H23' | 1.000 |
C14'—C15' | 1.517 (14) | C24'—C25' | 1.532 (14) |
C14'—H14' | 1.000 | C24'—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' | 1.000 | C25'—H25' | 1.000 |
C16'—O16' | 1.441 (14) | C26'—O26' | 1.443 (17) |
C16'—H16A' | 0.999 | C26'—H26A' | 1.000 |
C16'—H16B' | 1.001 | C26'—H26B' | 1.000 |
O11'—HO11' | 0.974 | O21'—HO21' | 0.972 |
O12'—HO12' | 0.985 | O22'—HO22' | 0.979 |
O13'—HO13' | 0.984 | O23'—HO23' | 0.987 |
O16'—HO16' | 0.975 | O26'—HO26' | 0.976 |
| | | |
O15—C11—O11 | 107.7 (8) | O21—C21—O25 | 112.9 (7) |
O15—C11—C12 | 112.6 (9) | O21—C21—C22 | 108.9 (7) |
O11—C11—C12 | 101.7 (8) | O25—C21—C22 | 111.1 (9) |
O15—C11—H11 | 110.7 | O21—C21—H21 | 107.9 |
O11—C11—H11 | 110.5 | O25—C21—H21 | 108.6 |
C12—C11—H11 | 113.1 | C22—C21—H21 | 107.3 |
O12—C12—C13 | 109.8 (8) | O22—C22—C23 | 111.2 (9) |
O12—C12—C11 | 114.8 (9) | O22—C22—C21 | 115.8 (9) |
C13—C12—C11 | 104.7 (7) | C23—C22—C21 | 107.8 (7) |
O12—C12—H12 | 109.3 | O22—C22—H22 | 106.3 |
C13—C12—H12 | 108.0 | C23—C22—H22 | 108.7 |
C11—C12—H12 | 110.0 | C21—C22—H22 | 106.6 |
O13—C13—C12 | 117.4 (9) | O23—C23—C22 | 115.8 (9) |
O13—C13—C14 | 109.0 (9) | O23—C23—C24 | 111.7 (9) |
C12—C13—C14 | 113.7 (8) | C22—C23—C24 | 114.8 (8) |
O13—C13—H13 | 103.7 | O23—C23—H23 | 104.1 |
C12—C13—H13 | 106.9 | C22—C23—H23 | 104.3 |
C14—C13—H13 | 104.8 | C24—C23—H23 | 104.4 |
O14—C14—C13 | 110.9 (10) | O24—C24—C25 | 108.2 (9) |
O14—C14—C15 | 104.1 (9) | O24—C24—C23 | 109.8 (9) |
C13—C14—C15 | 113.1 (8) | C25—C24—C23 | 112.4 (8) |
O14—C14—H14 | 107.9 | O24—C24—H24 | 109.9 |
C13—C14—H14 | 111.3 | C25—C24—H24 | 108.9 |
C15—C14—H14 | 109.3 | C23—C24—H24 | 107.7 |
O15—C15—C16 | 113.9 (8) | O25—C25—C24 | 112.8 (9) |
O15—C15—C14 | 112.8 (9) | O25—C25—C26 | 113.8 (9) |
C16—C15—C14 | 112.8 (8) | C24—C25—C26 | 114.6 (8) |
O15—C15—H15 | 105.4 | O25—C25—H25 | 106.0 |
C16—C15—H15 | 105.1 | C24—C25—H25 | 104.7 |
C14—C15—H15 | 105.9 | C26—C25—H25 | 103.7 |
O16—C16—C15 | 107.1 (10) | O26—C26—C25 | 99.9 (9) |
O16—C16—H16A | 110.4 | O26—C26—H26A | 112.5 |
C15—C16—H16A | 108.5 | C25—C26—H26A | 110.1 |
O16—C16—H16B | 112.4 | O26—C26—H26B | 113.3 |
C15—C16—H16B | 111.5 | C25—C26—H26B | 114.1 |
H16A—C16—H16B | 107.0 | H26A—C26—H26B | 107.0 |
C11—O11—C14' | 119.8 (8) | C21—O21—C24' | 115.1 (6) |
C12—O12—HO12 | 107.8 | C22—O22—HO22 | 113.2 |
C13—O13—HO13 | 105.9 | C23—O23—HO23 | 109.7 |
C14—O14—HO14 | 107.2 | C24—O24—HO24 | 118.7 |
C11—O15—C15 | 109.1 (8) | C21—O25—C25 | 112.0 (8) |
C16—O16—HO16 | 109.0 | C26—O26—HO26 | 107.2 |
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' | 108.4 | O21'—C21'—H21' | 115.2 |
O15'—C11'—H11' | 108.5 | O25'—C21'—H21' | 112.1 |
C12'—C11'—H11' | 108.5 | C22'—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' | 105.3 | O22'—C22'—H22' | 105.2 |
C11'—C12'—H12' | 104.4 | C23'—C22'—H22' | 107.9 |
C13'—C12'—H12' | 104.3 | C21'—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' | 105.0 | O23'—C23'—H23' | 109.5 |
C12'—C13'—H13' | 103.8 | C24'—C23'—H23' | 108.4 |
C14'—C13'—H13' | 103.2 | C22'—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' | 105.3 | O21—C24'—H24' | 109.4 |
C15'—C14'—H14' | 106.7 | C23'—C24'—H24' | 108.7 |
C13'—C14'—H14' | 107.0 | C25'—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' | 112.4 | O25'—C25'—H25' | 108.8 |
C16'—C15'—H15' | 113.5 | C26'—C25'—H25' | 109.9 |
C14'—C15'—H15' | 111.8 | C24'—C25'—H25' | 108.8 |
O16'—C16'—C15' | 120.2 (9) | O26'—C26'—C25' | 110.1 (11) |
O16'—C16'—H16A' | 110.6 | O26'—C26'—H26A' | 108.4 |
C15'—C16'—H16A' | 107.4 | C25'—C26'—H26A' | 110.0 |
O16'—C16'—H16B' | 105.2 | O26'—C26'—H26B' | 110.5 |
C15'—C16'—H16B' | 105.5 | C25'—C26'—H26B' | 110.7 |
H16A'—C16'—H16B' | 107.0 | H26A'—C26'—H26B' | 107.0 |
C11'—O11'—HO11' | 108.5 | C21'—O21'—HO21' | 102.5 |
C12'—O12'—HO12' | 106.7 | C22'—O22'—HO22' | 104.6 |
C13'—O13'—HO13' | 109.5 | C23'—O23'—HO23' | 110.3 |
C11'—O15'—C15' | 116.3 (9) | C25'—O25'—C21' | 119.0 (9) |
C16'—O16'—HO16' | 108.1 | C26'—O26'—HO26' | 73.7 |
| | | |
O15—C11—C12—O12 | −176.0 (10) | O21—C21—C22—O22 | −50.8 (13) |
O11—C11—C12—O12 | −61.0 (12) | O25—C21—C22—O22 | −175.7 (11) |
O15—C11—C12—C13 | 63.5 (11) | O21—C21—C22—C23 | −176.1 (8) |
O11—C11—C12—C13 | 178.5 (9) | O25—C21—C22—C23 | 59.0 (12) |
O12—C12—C13—O13 | 57.2 (14) | O22—C22—C23—O23 | 51.0 (15) |
C11—C12—C13—O13 | −179.0 (10) | C21—C22—C23—O23 | 179.0 (10) |
O12—C12—C13—C14 | −173.9 (10) | O22—C22—C23—C24 | −176.3 (10) |
C11—C12—C13—C14 | −50.1 (12) | C21—C22—C23—C24 | −48.3 (13) |
O13—C13—C14—O14 | 61.0 (13) | O23—C23—C24—O24 | 56.7 (14) |
C12—C13—C14—O14 | −72.0 (12) | C22—C23—C24—O24 | −77.8 (13) |
O13—C13—C14—C15 | 177.4 (10) | O23—C23—C24—C25 | 177.1 (10) |
C12—C13—C14—C15 | 44.4 (13) | C22—C23—C24—C25 | 42.6 (13) |
O14—C14—C15—O15 | 74.3 (12) | O24—C24—C25—O25 | 76.5 (13) |
C13—C14—C15—O15 | −46.0 (13) | C23—C24—C25—O25 | −44.8 (13) |
O14—C14—C15—C16 | −56.5 (13) | O24—C24—C25—C26 | −55.9 (13) |
C13—C14—C15—C16 | −176.8 (10) | C23—C24—C25—C26 | −177.2 (10) |
O15—C15—C16—O16 | 47.6 (15) | O25—C25—C26—O26 | 45.3 (14) |
C14—C15—C16—O16 | 177.8 (11) | C24—C25—C26—O26 | 177.1 (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—C15 | −179.9 (10) | O21—C21—O25—C25 | 172.3 (9) |
C12—C11—O15—C15 | −68.6 (12) | C22—C21—O25—C25 | −65.1 (13) |
C16—C15—O15—C11 | −172.7 (10) | C24—C25—O25—C21 | 57.1 (13) |
C14—C15—O15—C11 | 57.1 (12) | C26—C25—O25—C21 | −170.2 (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'—O11 | −59.7 (17) | O23'—C23'—C24'—O21 | −71.5 (12) |
C12'—C13'—C14'—O11 | 172.2 (10) | C22'—C23'—C24'—O21 | 165.5 (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···A | D—H | H···A | D···A | D—H···A |
O12—HO12···O13′i | 0.99 (2) | 1.85 (2) | 2.80 (2) | 159.4 (14) |
O13—HO13···O16i | 0.99 (2) | 1.89 (2) | 2.71 (2) | 139.2 (15) |
O14—HO14···O25?ii | 0.99 (2) | 2.18 (2) | 2.99 (2) | 138.0 (14) |
O16—HO16···O13iii | 0.99 (2) | 1.93 (2) | 2.88 (2) | 161.0 (18) |
O11?—HO11?···O23iv | 0.97 (2) | 1.85 (2) | 2.77 (2) | 157 (2) |
O12?—HO12?···O12iii | 0.99 (2) | 1.87 (2) | 2.80 (2) | 156 (2) |
O13?—HO13?···O15 | 0.98 (2) | 1.91 (2) | 2.643 (19) | 129 (1) |
O16?—HO16?···O12?v | 0.98 (2) | 1.86 (2) | 2.679 (19) | 140 (1) |
O22—HO22···O23?vi | 0.98 (2) | 1.81 (2) | 2.77 (2) | 166.3 (15) |
O23—HO23···O26vi | 0.98 (2) | 1.85 (2) | 2.81 (2) | 166.5 (14) |
O24—HO24···O15?vii | 0.98 (2) | 2.449 (19) | 2.681 (18) | 89.8 (12) |
O26—HO26···O22v | 0.938 (19) | 1.98 (2) | 2.706 (19) | 132.3 (17) |
O21′—HO21?···O13viii | 0.97 (2) | 1.86 (2) | 2.683 (19) | 141 (1) |
O22?—HO22?···O26?v | 0.98 (3) | 1.87 (2) | 2.75 (2) | 148 (2) |
O23?—HO23?···O25 | 0.99 (2) | 2.02 (2) | 2.84 (2) | 140 (1) |
O26?—HO26?···O22?vi | 0.98 (2) | 2.19 (3) | 2.76 (3) | 116 (2) |
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) x+1, y, z+1; (iv) x, y, z+1; (v) x−1, y, z−1; (vi) x+1, y, z; (vii) x, y, z−1; (viii) x, y−1, z. |
Experimental details
Crystal data |
Chemical formula | C12H22O11 |
Mr | 342.30 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 720.18 (3) |
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 = 2.662, Rwp = 3.511, Rexp = 1.586, RBragg = 1.607, χ2 = NOT FOUND |
No. of data points | 3946 |
No. of parameters | 195 |
No. of restraints | 118 |
Selected geometric parameters (Å, º) topC11—O15 | 1.415 (12) | C21—O21 | 1.406 (9) |
C11—O11 | 1.416 (15) | C21—O25 | 1.430 (16) |
C11—C12 | 1.538 (13) | C21—C22 | 1.527 (14) |
C12—O12 | 1.434 (13) | C22—O22 | 1.439 (16) |
C12—C13 | 1.516 (15) | C22—C23 | 1.515 (12) |
C13—O13 | 1.430 (15) | C23—O23 | 1.420 (15) |
C13—C14 | 1.518 (12) | C23—C24 | 1.533 (14) |
C14—O14 | 1.415 (16) | C24—O24 | 1.420 (14) |
C14—C15 | 1.521 (13) | C24—C25 | 1.512 (13) |
C15—O15 | 1.419 (15) | C25—O25 | 1.441 (12) |
C15—C16 | 1.503 (12) | C25—C26 | 1.520 (15) |
C16—O16 | 1.431 (17) | C26—O26 | 1.442 (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—O11 | 107.7 (8) | O21—C21—O25 | 112.9 (7) |
O15—C11—C12 | 112.6 (9) | O21—C21—C22 | 108.9 (7) |
O11—C11—C12 | 101.7 (8) | O25—C21—C22 | 111.1 (9) |
O12—C12—C13 | 109.8 (8) | O22—C22—C23 | 111.2 (9) |
O12—C12—C11 | 114.8 (9) | O22—C22—C21 | 115.8 (9) |
C13—C12—C11 | 104.7 (7) | C23—C22—C21 | 107.8 (7) |
O13—C13—C12 | 117.4 (9) | O23—C23—C22 | 115.8 (9) |
O13—C13—C14 | 109.0 (9) | O23—C23—C24 | 111.7 (9) |
C12—C13—C14 | 113.7 (8) | C22—C23—C24 | 114.8 (8) |
O14—C14—C13 | 110.9 (10) | O24—C24—C25 | 108.2 (9) |
O14—C14—C15 | 104.1 (9) | O24—C24—C23 | 109.8 (9) |
C13—C14—C15 | 113.1 (8) | C25—C24—C23 | 112.4 (8) |
O15—C15—C16 | 113.9 (8) | O25—C25—C24 | 112.8 (9) |
O15—C15—C14 | 112.8 (9) | O25—C25—C26 | 113.8 (9) |
C16—C15—C14 | 112.8 (8) | C24—C25—C26 | 114.6 (8) |
O16—C16—C15 | 107.1 (10) | O26—C26—C25 | 99.9 (9) |
C11—O11—C14' | 119.8 (8) | C21—O21—C24' | 115.1 (6) |
C11—O15—C15 | 109.1 (8) | C21—O25—C25 | 112.0 (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—O12 | −176.0 (10) | O21—C21—C22—O22 | −50.8 (13) |
O11—C11—C12—O12 | −61.0 (12) | O25—C21—C22—O22 | −175.7 (11) |
O15—C11—C12—C13 | 63.5 (11) | O21—C21—C22—C23 | −176.1 (8) |
O11—C11—C12—C13 | 178.5 (9) | O25—C21—C22—C23 | 59.0 (12) |
O12—C12—C13—O13 | 57.2 (14) | O22—C22—C23—O23 | 51.0 (15) |
C11—C12—C13—O13 | −179.0 (10) | C21—C22—C23—O23 | 179.0 (10) |
O12—C12—C13—C14 | −173.9 (10) | O22—C22—C23—C24 | −176.3 (10) |
C11—C12—C13—C14 | −50.1 (12) | C21—C22—C23—C24 | −48.3 (13) |
O13—C13—C14—O14 | 61.0 (13) | O23—C23—C24—O24 | 56.7 (14) |
C12—C13—C14—O14 | −72.0 (12) | C22—C23—C24—O24 | −77.8 (13) |
O13—C13—C14—C15 | 177.4 (10) | O23—C23—C24—C25 | 177.1 (10) |
C12—C13—C14—C15 | 44.4 (13) | C22—C23—C24—C25 | 42.6 (13) |
O14—C14—C15—O15 | 74.3 (12) | O24—C24—C25—O25 | 76.5 (13) |
C13—C14—C15—O15 | −46.0 (13) | C23—C24—C25—O25 | −44.8 (13) |
O14—C14—C15—C16 | −56.5 (13) | O24—C24—C25—C26 | −55.9 (13) |
C13—C14—C15—C16 | −176.8 (10) | C23—C24—C25—C26 | −177.2 (10) |
O15—C15—C16—O16 | 47.6 (15) | O25—C25—C26—O26 | 45.3 (14) |
C14—C15—C16—O16 | 177.8 (11) | C24—C25—C26—O26 | 177.1 (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—C15 | −179.9 (10) | O21—C21—O25—C25 | 172.3 (9) |
C12—C11—O15—C15 | −68.6 (12) | C22—C21—O25—C25 | −65.1 (13) |
C16—C15—O15—C11 | −172.7 (10) | C24—C25—O25—C21 | 57.1 (13) |
C14—C15—O15—C11 | 57.1 (12) | C26—C25—O25—C21 | −170.2 (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'—O11 | −59.7 (17) | O23'—C23'—C24'—O21 | −71.5 (12) |
C12'—C13'—C14'—O11 | 172.2 (10) | C22'—C23'—C24'—O21 | 165.5 (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···A | D—H | H···A | D···A | D—H···A |
O12—HO12···O13'i | 0.985 (21) | 1.852 (22) | 2.797 (23) | 159.4 (14) |
O13—HO13···O16i | 0.986 (22) | 1.887 (24) | 2.711 (24) | 139.2 (15) |
O14—HO14···O25?ii | 0.986 (21) | 2.184 (20) | 2.991 (20) | 138.0 (14) |
O16—HO16···O13iii | 0.986 (22) | 1.928 (22) | 2.878 (22) | 161.0 (18) |
O11?—HO11?···O23iv | 0.974 (21) | 1.850 (21) | 2.771 (21) | 156.7 (16) |
O12?—HO12?···O12iii | 0.985 (21) | 1.874 (21) | 2.803 (20) | 156.2 (16) |
O13?—HO13?···O15 | 0.984 (20) | 1.911 (18) | 2.643 (19) | 128.9 (14) |
O16?—HO16?···O12?v | 0.975 (19) | 1.862 (18) | 2.679 (19) | 139.5 (13) |
O22—HO22···O23?vi | 0.980 (22) | 1.811 (22) | 2.773 (22) | 166.3 (15) |
O23—HO23···O26vi | 0.982 (21) | 1.849 (23) | 2.813 (22) | 166.5 (14) |
O24—HO24···O15?vii | 0.982 (21) | 2.449 (19) | 2.681 (18) | 89.8 (12) |
O26—HO26···O22v | 0.938 (19) | 1.984 (20) | 2.706 (19) | 132.3 (17) |
O21'—HO21?···O13viii | 0.972 (18) | 1.855 (19) | 2.683 (19) | 141.4 (14) |
O22?—HO22?···O26?v | 0.979 (25) | 1.872 (22) | 2.752 (24) | 148.0 (19) |
O23?—HO23?···O25 | 0.987 (22) | 2.017 (19) | 2.841 (20) | 139.5 (14) |
O26?—HO26?···O22?vi | 0.976 (19) | 2.192 (27) | 2.763 (26) | 116.1 (15) |
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) x+1, y, z+1; (iv) x, y, z+1; (v) x−1, y, z−1; (vi) x+1, y, z; (vii) x, y, z−1; (viii) x, y−1, z. |