organic compounds
Methyl 6-O-trityl-α-D-glucopyranoside methanol disolvate
aDepartment of Chemistry, Çankırı Karatekin University, TR-18100, Çankırı, Turkey, bDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey, and cUniversität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
*Correspondence e-mail: merzifon@hacettepe.edu.tr
The 26H28O6·2CH3OH, contains two independent methyl 6-O-trityl-α-D-glucopyranoside molecules and four methanol solvent molecules. The rings of two methyl α-D-glucopyranoside adopt chair conformations. In the crystal, extensive intra- and intermolecular O—H⋯O and C—H⋯O hydrogen bonds link the molecules into a three-dimensional supramolecular architecture.
of the title compound, CCCDC reference: 993298
Related literature
For intramolecular 1,3-dipolar cycloadditions of various et al. (1994); Kleban et al. (2001); Dransfield et al. (1999); Gallos et al. (1999). For the importance of the title compound for the preparation of di- and trisaccharide analogues after several steps, see: Peri et al. (2002, 2004); Lopez et al. (2011). For the use of alkyl-5-enyl as intermediates for the syntheses of bicyclo[x.3.0] or bicyclo[x.2.1] derivatives after 1,3-dipolar cycloadditions, see: Dransfield et al. (1999). For the preparation of the title compound, see: Horton & Lauterback (1969); Bernet & Vasella (1979); Komiotis et al. (2006). For ring puckering parameters, see: Cremer & Pople (1975).
see: KobayashiExperimental
Crystal data
|
Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 993298
10.1107/S1600536814006461/xu5777sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814006461/xu5777Isup2.hkl
The title compound was synthesized by the literature method (Horton et al., 1969; Bernet & Vasella, 1979; Komiotis et al., 2006). α-D-glucopyranoside (10.0 g, 51.49 mmol) and triphenyl methyl chloride (14.4 g, 52.0 mmol) in pyridine (100 ml) was heated for 3 h at 373 K under argon atmosphere, and then the yellowish solution was stirred overnight at room temperature for 24 h. Pyridine was removed in vacuo and water (100 ml) was added to the mixture. The crude mixture was extracted with EtOAc (4 × 50 ml). Combined organic layer was dried over MgSO4, filtered and the solvent was removed in vacuo. Crystallization of the crude product in MeOH:petroleum ether (5:1) gave a colorless crystalline solid (yield: 80%), m.p.: 410–411 K, literature m.p.: 421-422 K (Bernet & Vasella, 1979).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms have been omitted for clarity. | |
Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity. |
C26H28O6·2CH4O | Z = 2 |
Mr = 500.57 | F(000) = 536 |
Triclinic, P1 | Dx = 1.194 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6763 (4) Å | Cell parameters from 10444 reflections |
b = 9.1233 (4) Å | θ = 2.1–26.5° |
c = 19.1545 (6) Å | µ = 0.09 mm−1 |
α = 86.328 (3)° | T = 299 K |
β = 82.578 (2)° | Block, colourless |
γ = 67.903 (2)° | 0.44 × 0.41 × 0.22 mm |
V = 1392.87 (10) Å3 |
Bruker Kappa APEXII DUO diffractometer | 11390 independent reflections |
Radiation source: fine-focus sealed tube | 10449 reflections with I > 2σ(I) |
Triumph monochromator | Rint = 0.017 |
ω + Phi Scans scans | θmax = 26.5°, θmin = 2.1° |
Absorption correction: multi-scan (Blessing, 1995) | h = −10→10 |
Tmin = 0.720, Tmax = 0.745 | k = −11→11 |
40377 measured reflections | l = −23→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0559P)2 + 0.1152P] where P = (Fo2 + 2Fc2)/3 |
11390 reflections | (Δ/σ)max = 0.001 |
695 parameters | Δρmax = 0.22 e Å−3 |
8 restraints | Δρmin = −0.24 e Å−3 |
C26H28O6·2CH4O | γ = 67.903 (2)° |
Mr = 500.57 | V = 1392.87 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.6763 (4) Å | Mo Kα radiation |
b = 9.1233 (4) Å | µ = 0.09 mm−1 |
c = 19.1545 (6) Å | T = 299 K |
α = 86.328 (3)° | 0.44 × 0.41 × 0.22 mm |
β = 82.578 (2)° |
Bruker Kappa APEXII DUO diffractometer | 11390 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 10449 reflections with I > 2σ(I) |
Tmin = 0.720, Tmax = 0.745 | Rint = 0.017 |
40377 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 8 restraints |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.22 e Å−3 |
11390 reflections | Δρmin = −0.24 e Å−3 |
695 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.67336 (14) | 0.99787 (12) | 0.09862 (5) | 0.0469 (3) | |
O2A | 0.77130 (15) | 0.98268 (14) | 0.20819 (6) | 0.0500 (3) | |
O3A | 0.46073 (17) | 1.02657 (14) | 0.27635 (6) | 0.0524 (3) | |
H31 | 0.369 (3) | 1.024 (3) | 0.2948 (12) | 0.063 (6)* | |
O4A | 0.40182 (15) | 0.77468 (16) | 0.21955 (7) | 0.0558 (3) | |
H41 | 0.428 (2) | 0.678 (3) | 0.2258 (10) | 0.053 (5)* | |
O5A | 0.67937 (16) | 0.59516 (13) | 0.11406 (7) | 0.0540 (3) | |
H51 | 0.603 (3) | 0.570 (4) | 0.1095 (17) | 0.109 (11)* | |
O6A | 0.92014 (12) | 0.84787 (12) | −0.01329 (5) | 0.0395 (2) | |
C1A | 0.6321 (2) | 1.04331 (18) | 0.16985 (8) | 0.0455 (4) | |
H1A | 0.5887 | 1.1591 | 0.1715 | 0.055* | |
C2A | 0.4962 (2) | 0.98605 (18) | 0.20406 (8) | 0.0435 (3) | |
H2A | 0.3946 | 1.0410 | 0.1811 | 0.052* | |
C3A | 0.54653 (19) | 0.81009 (18) | 0.19520 (8) | 0.0426 (3) | |
H3A | 0.6359 | 0.7528 | 0.2245 | 0.051* | |
C4A | 0.60696 (19) | 0.76254 (17) | 0.11881 (8) | 0.0417 (3) | |
H4A | 0.5117 | 0.8032 | 0.0911 | 0.050* | |
C5A | 0.7386 (2) | 0.82993 (17) | 0.08876 (8) | 0.0403 (3) | |
H5A | 0.8398 | 0.7802 | 0.1125 | 0.048* | |
C6A | 0.7810 (2) | 0.80281 (19) | 0.01065 (8) | 0.0420 (3) | |
H61 | 0.8092 | 0.6921 | 0.0009 | 0.050* | |
H62 | 0.6854 | 0.8654 | −0.0137 | 0.050* | |
C7A | 0.95558 (17) | 0.85998 (17) | −0.08845 (7) | 0.0361 (3) | |
C8A | 0.97374 (18) | 0.70260 (18) | −0.11965 (7) | 0.0391 (3) | |
C9A | 0.8427 (2) | 0.6814 (2) | −0.14656 (9) | 0.0507 (4) | |
H9A | 0.7465 | 0.7687 | −0.1536 | 0.061* | |
C10A | 0.8531 (3) | 0.5325 (3) | −0.16304 (10) | 0.0630 (5) | |
H10A | 0.7639 | 0.5206 | −0.1810 | 0.076* | |
C11A | 0.9938 (3) | 0.4019 (2) | −0.15317 (11) | 0.0669 (5) | |
H11A | 0.9999 | 0.3017 | −0.1638 | 0.080* | |
C12A | 1.1259 (3) | 0.4207 (2) | −0.12731 (11) | 0.0631 (5) | |
H12A | 1.2222 | 0.3330 | −0.1209 | 0.076* | |
C13A | 1.1161 (2) | 0.5697 (2) | −0.11083 (9) | 0.0491 (4) | |
H13A | 1.2064 | 0.5809 | −0.0936 | 0.059* | |
C14A | 1.11908 (17) | 0.89096 (17) | −0.10031 (8) | 0.0391 (3) | |
C15A | 1.1670 (2) | 0.9576 (2) | −0.04791 (10) | 0.0500 (4) | |
H15A | 1.1047 | 0.9754 | −0.0038 | 0.060* | |
C16A | 1.3061 (2) | 0.9976 (2) | −0.06079 (12) | 0.0609 (5) | |
H16A | 1.3378 | 1.0407 | −0.0250 | 0.073* | |
C17A | 1.3989 (2) | 0.9746 (2) | −0.12582 (12) | 0.0594 (5) | |
H17A | 1.4915 | 1.0039 | −0.1344 | 0.071* | |
C18A | 1.3531 (2) | 0.9083 (3) | −0.17757 (11) | 0.0649 (5) | |
H18A | 1.4155 | 0.8917 | −0.2216 | 0.078* | |
C19A | 1.2146 (2) | 0.8655 (2) | −0.16514 (9) | 0.0559 (4) | |
H19A | 1.1857 | 0.8193 | −0.2007 | 0.067* | |
C20A | 0.82246 (17) | 1.00806 (18) | −0.11745 (8) | 0.0400 (3) | |
C21A | 0.8104 (2) | 1.0315 (2) | −0.18955 (9) | 0.0488 (4) | |
H21A | 0.8777 | 0.9529 | −0.2209 | 0.059* | |
C22A | 0.6979 (2) | 1.1721 (2) | −0.21449 (11) | 0.0607 (5) | |
H22A | 0.6912 | 1.1873 | −0.2626 | 0.073* | |
C23A | 0.5971 (2) | 1.2884 (2) | −0.16949 (13) | 0.0652 (5) | |
H23A | 0.5202 | 1.3809 | −0.1868 | 0.078* | |
C24A | 0.6096 (2) | 1.2681 (2) | −0.09873 (13) | 0.0634 (5) | |
H24A | 0.5418 | 1.3480 | −0.0681 | 0.076* | |
C25A | 0.7224 (2) | 1.12958 (19) | −0.07223 (10) | 0.0493 (4) | |
H25A | 0.7311 | 1.1180 | −0.0241 | 0.059* | |
C26A | 0.9017 (3) | 1.0390 (3) | 0.18293 (12) | 0.0714 (5) | |
H261 | 0.9538 | 0.9937 | 0.1380 | 0.107* | |
H263 | 0.9836 | 1.0090 | 0.2157 | 0.107* | |
H262 | 0.8552 | 1.1522 | 0.1782 | 0.107* | |
O1B | 0.31293 (14) | 0.45350 (12) | 0.37621 (5) | 0.0440 (2) | |
O2B | 0.47236 (14) | 0.45945 (14) | 0.26845 (6) | 0.0500 (3) | |
O3B | 0.25027 (18) | 0.39417 (14) | 0.19786 (6) | 0.0551 (3) | |
H32 | 0.163 (3) | 0.406 (3) | 0.1816 (12) | 0.062 (6)* | |
O4B | −0.05021 (16) | 0.65235 (17) | 0.24352 (7) | 0.0553 (3) | |
H42 | −0.090 (3) | 0.743 (3) | 0.2394 (12) | 0.069 (7)* | |
O5B | −0.00591 (17) | 0.84545 (13) | 0.35104 (7) | 0.0526 (3) | |
H52 | −0.107 (4) | 0.874 (3) | 0.3576 (14) | 0.084 (8)* | |
O6B | 0.07427 (12) | 0.59786 (12) | 0.49097 (5) | 0.0394 (2) | |
C1B | 0.3571 (2) | 0.39980 (18) | 0.30618 (8) | 0.0431 (3) | |
H1B | 0.4087 | 0.2840 | 0.3073 | 0.052* | |
C2B | 0.2021 (2) | 0.44796 (18) | 0.26809 (8) | 0.0445 (3) | |
H2B | 0.1308 | 0.3936 | 0.2915 | 0.053* | |
C3B | 0.10178 (19) | 0.62449 (17) | 0.27215 (8) | 0.0416 (3) | |
H3B | 0.1643 | 0.6819 | 0.2440 | 0.050* | |
C4B | 0.06732 (18) | 0.67721 (16) | 0.34836 (8) | 0.0407 (3) | |
H4B | −0.0100 | 0.6326 | 0.3746 | 0.049* | |
C5B | 0.22883 (19) | 0.62183 (17) | 0.38259 (8) | 0.0385 (3) | |
H5B | 0.3019 | 0.6741 | 0.3589 | 0.046* | |
C6B | 0.19910 (19) | 0.65638 (18) | 0.46040 (8) | 0.0402 (3) | |
H63 | 0.3018 | 0.6044 | 0.4819 | 0.048* | |
H64 | 0.1613 | 0.7694 | 0.4676 | 0.048* | |
C7B | 0.04814 (17) | 0.58957 (16) | 0.56649 (7) | 0.0356 (3) | |
C8B | −0.11496 (17) | 0.55913 (17) | 0.58210 (8) | 0.0394 (3) | |
C9B | −0.1615 (2) | 0.4821 (2) | 0.53349 (10) | 0.0507 (4) | |
H9B | −0.0971 | 0.4555 | 0.4901 | 0.061* | |
C10B | −0.3025 (2) | 0.4443 (2) | 0.54856 (13) | 0.0646 (5) | |
H10B | −0.3328 | 0.3941 | 0.5150 | 0.078* | |
C11B | −0.3973 (2) | 0.4798 (2) | 0.61202 (14) | 0.0682 (6) | |
H11B | −0.4910 | 0.4525 | 0.6221 | 0.082* | |
C12B | −0.3539 (2) | 0.5559 (3) | 0.66101 (13) | 0.0708 (6) | |
H12B | −0.4184 | 0.5805 | 0.7044 | 0.085* | |
C13B | −0.2129 (2) | 0.5970 (2) | 0.64601 (10) | 0.0564 (4) | |
H13B | −0.1851 | 0.6500 | 0.6793 | 0.068* | |
C14B | 0.18515 (17) | 0.44195 (17) | 0.59409 (8) | 0.0371 (3) | |
C15B | 0.2934 (2) | 0.32726 (18) | 0.54781 (9) | 0.0462 (3) | |
H15B | 0.2885 | 0.3434 | 0.4996 | 0.055* | |
C16B | 0.4089 (2) | 0.1890 (2) | 0.57281 (11) | 0.0576 (4) | |
H16B | 0.4813 | 0.1138 | 0.5411 | 0.069* | |
C17B | 0.4176 (2) | 0.1617 (2) | 0.64408 (11) | 0.0602 (5) | |
H17B | 0.4956 | 0.0688 | 0.6605 | 0.072* | |
C18B | 0.3093 (2) | 0.2737 (2) | 0.69066 (10) | 0.0572 (4) | |
H18B | 0.3133 | 0.2558 | 0.7389 | 0.069* | |
C19B | 0.1945 (2) | 0.4127 (2) | 0.66593 (9) | 0.0468 (4) | |
H19B | 0.1226 | 0.4876 | 0.6979 | 0.056* | |
C20B | 0.03483 (18) | 0.74705 (18) | 0.59505 (8) | 0.0382 (3) | |
C21B | 0.1630 (2) | 0.7665 (2) | 0.62465 (10) | 0.0520 (4) | |
H21B | 0.2559 | 0.6783 | 0.6345 | 0.062* | |
C22B | 0.1543 (3) | 0.9163 (3) | 0.63984 (11) | 0.0672 (5) | |
H22B | 0.2419 | 0.9274 | 0.6595 | 0.081* | |
C23B | 0.0185 (3) | 1.0479 (2) | 0.62629 (11) | 0.0683 (6) | |
H23B | 0.0134 | 1.1480 | 0.6365 | 0.082* | |
C24B | −0.1096 (3) | 1.0302 (2) | 0.59751 (12) | 0.0690 (5) | |
H24B | −0.2025 | 1.1190 | 0.5882 | 0.083* | |
C25B | −0.1021 (2) | 0.8817 (2) | 0.58215 (10) | 0.0534 (4) | |
H25B | −0.1906 | 0.8718 | 0.5628 | 0.064* | |
C26B | 0.6300 (2) | 0.4008 (3) | 0.29548 (12) | 0.0728 (6) | |
H264 | 0.6175 | 0.4420 | 0.3416 | 0.109* | |
H265 | 0.7083 | 0.4336 | 0.2649 | 0.109* | |
H266 | 0.6706 | 0.2874 | 0.2982 | 0.109* | |
O7 | −0.0018 (2) | 0.3825 (2) | 0.13088 (9) | 0.0811 (4) | |
H71 | −0.092 (2) | 0.449 (3) | 0.1299 (13) | 0.082 (9)* | |
O8 | 0.4376 (2) | 0.4936 (2) | 0.09441 (9) | 0.0781 (4) | |
O9 | 0.6599 (2) | 0.9282 (2) | 0.38342 (12) | 0.0916 (5) | |
O10 | 0.1595 (2) | 1.0518 (2) | 0.34549 (10) | 0.0950 (6) | |
C27 | 0.0464 (4) | 0.3127 (4) | 0.06554 (15) | 0.1008 (9) | |
H271 | 0.0039 | 0.3911 | 0.0297 | 0.151* | |
H272 | 0.0023 | 0.2310 | 0.0642 | 0.151* | |
H273 | 0.1664 | 0.2676 | 0.0573 | 0.151* | |
C28 | 0.3102 (5) | 0.6022 (5) | 0.05810 (18) | 0.1225 (12) | |
H281 | 0.2410 | 0.6870 | 0.0887 | 0.184* | |
H282 | 0.2433 | 0.5497 | 0.0429 | 0.184* | |
H283 | 0.3594 | 0.6440 | 0.0178 | 0.184* | |
H81 | 0.387 (3) | 0.455 (3) | 0.1307 (15) | 0.087 (8)* | |
C29 | 0.5938 (4) | 0.8244 (5) | 0.42249 (18) | 0.1127 (10) | |
H291 | 0.6489 | 0.7889 | 0.4642 | 0.169* | |
H292 | 0.6115 | 0.7348 | 0.3943 | 0.169* | |
H293 | 0.4759 | 0.8787 | 0.4355 | 0.169* | |
H91 | 0.613 (5) | 0.953 (5) | 0.346 (2) | 0.130 (14)* | |
C30 | 0.0938 (5) | 1.1398 (3) | 0.40562 (15) | 0.1068 (10) | |
H301 | 0.1386 | 1.2213 | 0.4054 | 0.160* | |
H302 | 0.1228 | 1.0722 | 0.4463 | 0.160* | |
H303 | −0.0259 | 1.1871 | 0.4071 | 0.160* | |
H101 | 0.120 (4) | 0.985 (3) | 0.3435 (16) | 0.103 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0607 (7) | 0.0393 (5) | 0.0398 (6) | −0.0214 (5) | 0.0035 (5) | 0.0041 (4) |
O2A | 0.0580 (7) | 0.0526 (6) | 0.0460 (6) | −0.0301 (5) | 0.0008 (5) | −0.0012 (5) |
O3A | 0.0587 (7) | 0.0506 (6) | 0.0464 (6) | −0.0227 (5) | 0.0109 (5) | −0.0090 (5) |
O4A | 0.0516 (7) | 0.0501 (7) | 0.0653 (7) | −0.0254 (5) | 0.0160 (5) | −0.0013 (5) |
O5A | 0.0555 (7) | 0.0428 (6) | 0.0648 (7) | −0.0238 (5) | 0.0098 (5) | −0.0077 (5) |
O6A | 0.0387 (5) | 0.0512 (6) | 0.0327 (5) | −0.0224 (5) | −0.0017 (4) | 0.0002 (4) |
C1A | 0.0581 (10) | 0.0359 (7) | 0.0424 (8) | −0.0202 (7) | 0.0025 (7) | 0.0004 (6) |
C2A | 0.0467 (8) | 0.0408 (8) | 0.0393 (8) | −0.0148 (6) | 0.0040 (6) | −0.0018 (6) |
C3A | 0.0416 (7) | 0.0436 (7) | 0.0428 (7) | −0.0196 (6) | 0.0047 (6) | 0.0021 (6) |
C4A | 0.0448 (8) | 0.0399 (7) | 0.0410 (7) | −0.0180 (6) | 0.0011 (6) | −0.0014 (5) |
C5A | 0.0440 (8) | 0.0403 (7) | 0.0373 (7) | −0.0179 (6) | −0.0008 (6) | 0.0006 (6) |
C6A | 0.0440 (8) | 0.0526 (8) | 0.0364 (7) | −0.0278 (7) | 0.0015 (6) | −0.0008 (6) |
C7A | 0.0330 (7) | 0.0448 (7) | 0.0321 (7) | −0.0169 (6) | −0.0014 (5) | 0.0006 (5) |
C8A | 0.0405 (8) | 0.0474 (8) | 0.0328 (7) | −0.0216 (6) | 0.0003 (6) | −0.0001 (6) |
C9A | 0.0488 (9) | 0.0592 (10) | 0.0519 (9) | −0.0290 (8) | −0.0051 (7) | −0.0018 (7) |
C10A | 0.0741 (13) | 0.0713 (12) | 0.0601 (11) | −0.0455 (11) | −0.0033 (9) | −0.0106 (9) |
C11A | 0.0933 (16) | 0.0548 (11) | 0.0603 (11) | −0.0403 (11) | 0.0093 (11) | −0.0116 (8) |
C12A | 0.0747 (13) | 0.0458 (9) | 0.0598 (11) | −0.0152 (9) | 0.0024 (9) | −0.0028 (8) |
C13A | 0.0465 (9) | 0.0498 (9) | 0.0478 (8) | −0.0146 (7) | −0.0044 (7) | −0.0017 (7) |
C14A | 0.0329 (7) | 0.0418 (7) | 0.0446 (8) | −0.0163 (6) | −0.0065 (6) | 0.0045 (6) |
C15A | 0.0442 (8) | 0.0528 (9) | 0.0561 (9) | −0.0218 (7) | −0.0012 (7) | −0.0094 (7) |
C16A | 0.0461 (9) | 0.0599 (10) | 0.0847 (13) | −0.0258 (8) | −0.0111 (9) | −0.0125 (9) |
C17A | 0.0350 (8) | 0.0511 (9) | 0.0938 (14) | −0.0194 (7) | −0.0047 (9) | 0.0038 (9) |
C18A | 0.0463 (10) | 0.0843 (13) | 0.0650 (12) | −0.0311 (9) | 0.0080 (8) | 0.0069 (10) |
C19A | 0.0453 (9) | 0.0831 (13) | 0.0472 (9) | −0.0348 (9) | 0.0003 (7) | 0.0004 (8) |
C20A | 0.0323 (7) | 0.0464 (8) | 0.0460 (8) | −0.0211 (6) | −0.0037 (6) | 0.0046 (6) |
C21A | 0.0418 (8) | 0.0609 (10) | 0.0457 (9) | −0.0224 (7) | −0.0067 (7) | 0.0092 (7) |
C22A | 0.0528 (10) | 0.0721 (12) | 0.0614 (11) | −0.0291 (9) | −0.0167 (9) | 0.0268 (9) |
C23A | 0.0461 (9) | 0.0555 (10) | 0.0935 (15) | −0.0190 (8) | −0.0185 (9) | 0.0258 (10) |
C24A | 0.0494 (10) | 0.0484 (9) | 0.0873 (15) | −0.0144 (8) | −0.0026 (9) | 0.0013 (9) |
C25A | 0.0462 (9) | 0.0483 (9) | 0.0551 (10) | −0.0197 (7) | −0.0051 (7) | −0.0001 (7) |
C26A | 0.0729 (13) | 0.0846 (14) | 0.0736 (12) | −0.0527 (12) | 0.0053 (10) | −0.0023 (10) |
O1B | 0.0516 (6) | 0.0404 (5) | 0.0357 (5) | −0.0132 (5) | −0.0033 (4) | 0.0024 (4) |
O2B | 0.0462 (6) | 0.0517 (6) | 0.0476 (6) | −0.0155 (5) | 0.0011 (5) | 0.0006 (5) |
O3B | 0.0622 (8) | 0.0591 (7) | 0.0436 (6) | −0.0208 (6) | −0.0053 (5) | −0.0110 (5) |
O4B | 0.0563 (7) | 0.0523 (7) | 0.0610 (7) | −0.0197 (6) | −0.0206 (6) | −0.0011 (5) |
O5B | 0.0505 (7) | 0.0426 (6) | 0.0617 (7) | −0.0131 (5) | −0.0065 (5) | −0.0060 (5) |
O6B | 0.0424 (5) | 0.0494 (6) | 0.0332 (5) | −0.0254 (5) | −0.0034 (4) | 0.0002 (4) |
C1B | 0.0503 (9) | 0.0349 (7) | 0.0402 (8) | −0.0129 (6) | −0.0009 (6) | −0.0006 (6) |
C2B | 0.0532 (9) | 0.0431 (8) | 0.0395 (8) | −0.0214 (7) | −0.0019 (6) | −0.0034 (6) |
C3B | 0.0457 (8) | 0.0427 (7) | 0.0398 (7) | −0.0200 (6) | −0.0078 (6) | 0.0025 (6) |
C4B | 0.0429 (8) | 0.0390 (7) | 0.0418 (7) | −0.0182 (6) | −0.0015 (6) | −0.0003 (5) |
C5B | 0.0422 (7) | 0.0402 (7) | 0.0360 (7) | −0.0206 (6) | 0.0020 (6) | −0.0009 (5) |
C6B | 0.0409 (8) | 0.0462 (8) | 0.0395 (8) | −0.0239 (6) | −0.0011 (6) | −0.0016 (6) |
C7B | 0.0310 (7) | 0.0432 (7) | 0.0346 (7) | −0.0171 (6) | −0.0021 (5) | 0.0023 (6) |
C8B | 0.0316 (7) | 0.0400 (7) | 0.0474 (8) | −0.0148 (6) | −0.0069 (6) | 0.0079 (6) |
C9B | 0.0453 (9) | 0.0496 (9) | 0.0638 (10) | −0.0249 (7) | −0.0074 (7) | 0.0000 (7) |
C10B | 0.0497 (10) | 0.0568 (10) | 0.0988 (16) | −0.0304 (9) | −0.0179 (10) | 0.0036 (10) |
C11B | 0.0387 (9) | 0.0571 (10) | 0.1128 (17) | −0.0258 (8) | −0.0073 (10) | 0.0174 (11) |
C12B | 0.0452 (10) | 0.0830 (14) | 0.0801 (14) | −0.0270 (10) | 0.0118 (9) | 0.0099 (11) |
C13B | 0.0452 (9) | 0.0735 (12) | 0.0534 (10) | −0.0288 (8) | 0.0035 (7) | 0.0020 (8) |
C14B | 0.0312 (7) | 0.0411 (7) | 0.0433 (8) | −0.0186 (6) | −0.0049 (6) | 0.0036 (6) |
C15B | 0.0441 (8) | 0.0439 (8) | 0.0509 (9) | −0.0161 (7) | −0.0058 (7) | −0.0042 (7) |
C16B | 0.0469 (9) | 0.0463 (9) | 0.0747 (12) | −0.0116 (7) | −0.0055 (8) | −0.0058 (8) |
C17B | 0.0446 (9) | 0.0495 (9) | 0.0840 (14) | −0.0147 (7) | −0.0170 (9) | 0.0174 (9) |
C18B | 0.0497 (10) | 0.0669 (11) | 0.0572 (10) | −0.0245 (8) | −0.0158 (8) | 0.0214 (8) |
C19B | 0.0400 (8) | 0.0542 (9) | 0.0456 (9) | −0.0182 (7) | −0.0033 (6) | 0.0054 (7) |
C20B | 0.0391 (7) | 0.0434 (7) | 0.0334 (7) | −0.0180 (6) | 0.0010 (6) | −0.0021 (5) |
C21B | 0.0512 (9) | 0.0520 (9) | 0.0589 (10) | −0.0237 (8) | −0.0130 (8) | −0.0016 (7) |
C22B | 0.0819 (14) | 0.0739 (13) | 0.0664 (12) | −0.0504 (12) | −0.0126 (10) | −0.0058 (10) |
C23B | 0.0938 (16) | 0.0496 (10) | 0.0679 (12) | −0.0366 (11) | 0.0044 (11) | −0.0116 (9) |
C24B | 0.0683 (12) | 0.0430 (10) | 0.0872 (15) | −0.0132 (9) | −0.0016 (11) | −0.0034 (9) |
C25B | 0.0487 (9) | 0.0473 (9) | 0.0624 (11) | −0.0159 (7) | −0.0073 (8) | 0.0004 (7) |
C26B | 0.0458 (10) | 0.0862 (14) | 0.0765 (13) | −0.0139 (9) | −0.0052 (9) | −0.0009 (11) |
O7 | 0.0757 (11) | 0.0799 (10) | 0.0832 (10) | −0.0174 (9) | −0.0141 (8) | −0.0317 (8) |
O8 | 0.0870 (11) | 0.0884 (11) | 0.0752 (10) | −0.0520 (9) | −0.0081 (8) | 0.0026 (8) |
O9 | 0.0637 (10) | 0.1045 (13) | 0.0961 (13) | −0.0189 (9) | −0.0153 (9) | 0.0075 (10) |
O10 | 0.0941 (12) | 0.1056 (13) | 0.1018 (13) | −0.0662 (11) | 0.0450 (10) | −0.0514 (10) |
C27 | 0.125 (2) | 0.0942 (19) | 0.0813 (16) | −0.0400 (17) | 0.0087 (15) | −0.0334 (14) |
C28 | 0.149 (3) | 0.160 (3) | 0.097 (2) | −0.094 (3) | −0.062 (2) | 0.051 (2) |
C29 | 0.108 (2) | 0.132 (3) | 0.101 (2) | −0.050 (2) | −0.0187 (17) | 0.0295 (19) |
C30 | 0.148 (3) | 0.0887 (17) | 0.0921 (18) | −0.0670 (18) | 0.0464 (18) | −0.0358 (14) |
O1A—C1A | 1.4130 (19) | C1B—H1B | 0.9800 |
O1A—C5A | 1.4355 (18) | C2B—O3B | 1.4179 (19) |
O2A—C26A | 1.429 (2) | C2B—C3B | 1.517 (2) |
O3A—H31 | 0.83 (2) | C2B—H2B | 0.9800 |
O4A—H41 | 0.83 (2) | C3B—O4B | 1.4216 (19) |
O5A—H51 | 0.795 (18) | C3B—C4B | 1.523 (2) |
O6A—C6A | 1.4296 (17) | C3B—H3B | 0.9800 |
O6A—C7A | 1.4389 (17) | C4B—O5B | 1.4248 (18) |
C1A—O2A | 1.407 (2) | C4B—C5B | 1.520 (2) |
C1A—C2A | 1.520 (2) | C4B—H4B | 0.9800 |
C1A—H1A | 0.9800 | C5B—C6B | 1.512 (2) |
C2A—O3A | 1.4209 (19) | C5B—H5B | 0.9800 |
C2A—C3A | 1.512 (2) | C6B—H63 | 0.9700 |
C2A—H2A | 0.9800 | C6B—H64 | 0.9700 |
C3A—O4A | 1.4258 (18) | C7B—C20B | 1.529 (2) |
C3A—C4A | 1.522 (2) | C7B—C8B | 1.5313 (19) |
C3A—H3A | 0.9800 | C7B—C14B | 1.540 (2) |
C4A—O5A | 1.4199 (18) | C8B—C13B | 1.380 (2) |
C4A—C5A | 1.525 (2) | C8B—C9B | 1.385 (2) |
C4A—H4A | 0.9800 | C9B—C10B | 1.383 (2) |
C5A—C6A | 1.507 (2) | C9B—H9B | 0.9300 |
C5A—H5A | 0.9800 | C10B—C11B | 1.360 (3) |
C6A—H61 | 0.9700 | C10B—H10B | 0.9300 |
C6A—H62 | 0.9700 | C11B—C12B | 1.370 (4) |
C7A—C14A | 1.5342 (19) | C11B—H11B | 0.9300 |
C7A—C8A | 1.536 (2) | C12B—C13B | 1.400 (3) |
C7A—C20A | 1.537 (2) | C12B—H12B | 0.9300 |
C8A—C9A | 1.388 (2) | C13B—H13B | 0.9300 |
C8A—C13A | 1.388 (2) | C14B—C15B | 1.388 (2) |
C9A—C10A | 1.382 (3) | C14B—C19B | 1.392 (2) |
C9A—H9A | 0.9300 | C15B—C16B | 1.385 (2) |
C10A—C11A | 1.372 (3) | C15B—H15B | 0.9300 |
C10A—H10A | 0.9300 | C16B—C17B | 1.379 (3) |
C11A—C12A | 1.376 (3) | C16B—H16B | 0.9300 |
C11A—H11A | 0.9300 | C17B—C18B | 1.379 (3) |
C12A—C13A | 1.384 (3) | C17B—H17B | 0.9300 |
C12A—H12A | 0.9300 | C18B—C19B | 1.385 (2) |
C13A—H13A | 0.9300 | C18B—H18B | 0.9300 |
C14A—C19A | 1.382 (2) | C19B—H19B | 0.9300 |
C14A—C15A | 1.388 (2) | C20B—C21B | 1.384 (2) |
C15A—C16A | 1.376 (2) | C20B—C25B | 1.386 (2) |
C15A—H15A | 0.9300 | C21B—C22B | 1.388 (3) |
C16A—C17A | 1.375 (3) | C21B—H21B | 0.9300 |
C16A—H16A | 0.9300 | C22B—C23B | 1.368 (3) |
C17A—C18A | 1.366 (3) | C22B—H22B | 0.9300 |
C17A—H17A | 0.9300 | C23B—C24B | 1.367 (3) |
C18A—C19A | 1.386 (3) | C23B—H23B | 0.9300 |
C18A—H18A | 0.9300 | C24B—C25B | 1.381 (3) |
C19A—H19A | 0.9300 | C24B—H24B | 0.9300 |
C20A—C25A | 1.392 (2) | C25B—H25B | 0.9300 |
C20A—C21A | 1.395 (2) | C26B—H264 | 0.9600 |
C21A—C22A | 1.389 (3) | C26B—H265 | 0.9600 |
C21A—H21A | 0.9300 | C26B—H266 | 0.9600 |
C22A—C23A | 1.363 (3) | O7—C27 | 1.383 (3) |
C22A—H22A | 0.9300 | O7—H71 | 0.789 (16) |
C23A—C24A | 1.369 (3) | O8—C28 | 1.404 (4) |
C23A—H23A | 0.9300 | O8—H81 | 0.90 (3) |
C24A—C25A | 1.389 (3) | O9—C29 | 1.412 (4) |
C24A—H24A | 0.9300 | O9—H91 | 0.85 (4) |
C25A—H25A | 0.9300 | O10—C30 | 1.379 (3) |
C26A—H261 | 0.9600 | O10—H101 | 0.802 (18) |
C26A—H263 | 0.9600 | C27—H271 | 0.9600 |
C26A—H262 | 0.9600 | C27—H272 | 0.9600 |
O1B—C1B | 1.4130 (18) | C27—H273 | 0.9600 |
O1B—C5B | 1.4365 (18) | C28—H281 | 0.9600 |
O2B—C26B | 1.422 (2) | C28—H282 | 0.9600 |
O3B—H32 | 0.82 (2) | C28—H283 | 0.9600 |
O4B—H42 | 0.77 (3) | C29—H291 | 0.9600 |
O5B—H52 | 0.81 (3) | C29—H292 | 0.9600 |
O6B—C6B | 1.4254 (17) | C29—H293 | 0.9600 |
O6B—C7B | 1.4366 (17) | C30—H301 | 0.9600 |
C1B—O2B | 1.411 (2) | C30—H302 | 0.9600 |
C1B—C2B | 1.517 (2) | C30—H303 | 0.9600 |
C1A—O1A—C5A | 114.19 (11) | O3B—C2B—H2B | 107.7 |
C1A—O2A—C26A | 113.39 (14) | C1B—C2B—H2B | 107.7 |
C2A—O3A—H31 | 113.4 (15) | C3B—C2B—C1B | 111.89 (12) |
C3A—O4A—H41 | 110.3 (14) | C3B—C2B—H2B | 107.7 |
C4A—O5A—H51 | 104 (2) | O4B—C3B—C2B | 106.85 (12) |
C6A—O6A—C7A | 115.66 (10) | O4B—C3B—C4B | 110.88 (12) |
O1A—C1A—C2A | 109.59 (13) | O4B—C3B—H3B | 109.6 |
O1A—C1A—H1A | 108.6 | C2B—C3B—C4B | 110.14 (12) |
O2A—C1A—O1A | 112.26 (13) | C2B—C3B—H3B | 109.6 |
O2A—C1A—C2A | 109.20 (12) | C4B—C3B—H3B | 109.6 |
O2A—C1A—H1A | 108.6 | O5B—C4B—C3B | 109.90 (12) |
C2A—C1A—H1A | 108.6 | O5B—C4B—C5B | 108.42 (12) |
O3A—C2A—C1A | 109.07 (13) | O5B—C4B—H4B | 109.3 |
O3A—C2A—C3A | 111.23 (12) | C3B—C4B—H4B | 109.3 |
O3A—C2A—H2A | 108.3 | C5B—C4B—C3B | 110.66 (12) |
C3A—C2A—C1A | 111.44 (12) | C5B—C4B—H4B | 109.3 |
C3A—C2A—H2A | 108.3 | O1B—C5B—C4B | 110.07 (11) |
C1A—C2A—H2A | 108.3 | O1B—C5B—C6B | 106.67 (12) |
O4A—C3A—C2A | 106.33 (12) | O1B—C5B—H5B | 109.1 |
O4A—C3A—C4A | 110.87 (12) | C4B—C5B—H5B | 109.1 |
O4A—C3A—H3A | 109.3 | C6B—C5B—C4B | 112.63 (12) |
C2A—C3A—C4A | 111.59 (12) | C6B—C5B—H5B | 109.1 |
C2A—C3A—H3A | 109.3 | O6B—C6B—C5B | 107.27 (11) |
C4A—C3A—H3A | 109.3 | O6B—C6B—H63 | 110.3 |
O5A—C4A—C3A | 110.08 (12) | O6B—C6B—H64 | 110.3 |
O5A—C4A—C5A | 108.50 (12) | C5B—C6B—H63 | 110.3 |
O5A—C4A—H4A | 109.2 | C5B—C6B—H64 | 110.3 |
C3A—C4A—C5A | 110.49 (12) | H63—C6B—H64 | 108.5 |
C3A—C4A—H4A | 109.2 | O6B—C7B—C8B | 104.16 (11) |
C5A—C4A—H4A | 109.2 | O6B—C7B—C14B | 110.02 (11) |
O1A—C5A—C4A | 109.63 (12) | O6B—C7B—C20B | 108.11 (11) |
O1A—C5A—C6A | 107.11 (12) | C8B—C7B—C14B | 105.82 (11) |
O1A—C5A—H5A | 109.8 | C20B—C7B—C8B | 112.91 (11) |
C6A—C5A—C4A | 110.63 (12) | C20B—C7B—C14B | 115.25 (12) |
C6A—C5A—H5A | 109.8 | C9B—C8B—C7B | 120.04 (14) |
C4A—C5A—H5A | 109.8 | C13B—C8B—C7B | 121.55 (15) |
O6A—C6A—C5A | 108.56 (12) | C13B—C8B—C9B | 118.26 (15) |
O6A—C6A—H61 | 110.0 | C8B—C9B—H9B | 119.6 |
O6A—C6A—H62 | 110.0 | C10B—C9B—C8B | 120.88 (18) |
C5A—C6A—H61 | 110.0 | C10B—C9B—H9B | 119.6 |
C5A—C6A—H62 | 110.0 | C9B—C10B—H10B | 119.7 |
H61—C6A—H62 | 108.4 | C11B—C10B—C9B | 120.7 (2) |
O6A—C7A—C8A | 107.53 (11) | C11B—C10B—H10B | 119.7 |
O6A—C7A—C14A | 105.38 (11) | C10B—C11B—C12B | 119.58 (17) |
O6A—C7A—C20A | 110.27 (11) | C10B—C11B—H11B | 120.2 |
C8A—C7A—C20A | 115.29 (12) | C12B—C11B—H11B | 120.2 |
C14A—C7A—C8A | 112.45 (11) | C11B—C12B—C13B | 120.3 (2) |
C14A—C7A—C20A | 105.50 (11) | C11B—C12B—H12B | 119.8 |
C9A—C8A—C7A | 122.39 (14) | C13B—C12B—H12B | 119.8 |
C9A—C8A—C13A | 117.77 (15) | C8B—C13B—C12B | 120.29 (19) |
C13A—C8A—C7A | 119.04 (13) | C8B—C13B—H13B | 119.9 |
C8A—C9A—H9A | 119.5 | C12B—C13B—H13B | 119.9 |
C10A—C9A—C8A | 120.97 (17) | C15B—C14B—C7B | 120.41 (13) |
C10A—C9A—H9A | 119.5 | C15B—C14B—C19B | 118.08 (14) |
C9A—C10A—H10A | 119.7 | C19B—C14B—C7B | 121.26 (13) |
C11A—C10A—C9A | 120.59 (19) | C14B—C15B—H15B | 119.7 |
C11A—C10A—H10A | 119.7 | C16B—C15B—C14B | 120.60 (16) |
C10A—C11A—C12A | 119.30 (18) | C16B—C15B—H15B | 119.7 |
C10A—C11A—H11A | 120.3 | C15B—C16B—H16B | 119.6 |
C12A—C11A—H11A | 120.3 | C17B—C16B—C15B | 120.80 (17) |
C11A—C12A—C13A | 120.31 (19) | C17B—C16B—H16B | 119.6 |
C11A—C12A—H12A | 119.8 | C16B—C17B—C18B | 119.20 (16) |
C13A—C12A—H12A | 119.8 | C16B—C17B—H17B | 120.4 |
C8A—C13A—H13A | 119.5 | C18B—C17B—H17B | 120.4 |
C12A—C13A—C8A | 121.05 (17) | C17B—C18B—C19B | 120.24 (17) |
C12A—C13A—H13A | 119.5 | C17B—C18B—H18B | 119.9 |
C15A—C14A—C7A | 120.58 (14) | C19B—C18B—H18B | 119.9 |
C19A—C14A—C7A | 120.79 (14) | C14B—C19B—H19B | 119.5 |
C19A—C14A—C15A | 118.41 (15) | C18B—C19B—C14B | 121.07 (16) |
C14A—C15A—H15A | 119.8 | C18B—C19B—H19B | 119.5 |
C16A—C15A—C14A | 120.39 (17) | C21B—C20B—C7B | 123.23 (14) |
C16A—C15A—H15A | 119.8 | C21B—C20B—C25B | 117.62 (15) |
C15A—C16A—H16A | 119.5 | C25B—C20B—C7B | 118.53 (14) |
C17A—C16A—C15A | 120.95 (18) | C20B—C21B—C22B | 120.69 (18) |
C17A—C16A—H16A | 119.5 | C20B—C21B—H21B | 119.7 |
C16A—C17A—H17A | 120.5 | C22B—C21B—H21B | 119.7 |
C18A—C17A—C16A | 119.01 (17) | C21B—C22B—H22B | 119.6 |
C18A—C17A—H17A | 120.5 | C23B—C22B—C21B | 120.79 (19) |
C17A—C18A—C19A | 120.73 (18) | C23B—C22B—H22B | 119.6 |
C17A—C18A—H18A | 119.6 | C24B—C23B—C22B | 119.11 (17) |
C19A—C18A—H18A | 119.6 | C24B—C23B—H23B | 120.4 |
C14A—C19A—C18A | 120.49 (17) | C22B—C23B—H23B | 120.4 |
C14A—C19A—H19A | 119.8 | C23B—C24B—C25B | 120.55 (19) |
C18A—C19A—H19A | 119.8 | C23B—C24B—H24B | 119.7 |
C21A—C20A—C7A | 121.38 (14) | C25B—C24B—H24B | 119.7 |
C25A—C20A—C7A | 119.85 (14) | C20B—C25B—H25B | 119.4 |
C25A—C20A—C21A | 118.44 (15) | C24B—C25B—C20B | 121.24 (18) |
C20A—C21A—H21A | 120.0 | C24B—C25B—H25B | 119.4 |
C22A—C21A—C20A | 119.97 (17) | O2B—C26B—H264 | 109.5 |
C22A—C21A—H21A | 120.0 | O2B—C26B—H265 | 109.5 |
C21A—C22A—H22A | 119.5 | O2B—C26B—H266 | 109.5 |
C23A—C22A—C21A | 121.01 (19) | H264—C26B—H265 | 109.5 |
C23A—C22A—H22A | 119.5 | H264—C26B—H266 | 109.5 |
C22A—C23A—C24A | 119.63 (17) | H265—C26B—H266 | 109.5 |
C22A—C23A—H23A | 120.2 | C27—O7—H71 | 107.5 (18) |
C24A—C23A—H23A | 120.2 | C28—O8—H81 | 106.8 (17) |
C23A—C24A—C25A | 120.72 (19) | C29—O9—H91 | 107 (3) |
C23A—C24A—H24A | 119.6 | C30—O10—H101 | 111 (2) |
C25A—C24A—H24A | 119.6 | O7—C27—H271 | 109.5 |
C20A—C25A—H25A | 119.9 | O7—C27—H272 | 109.5 |
C24A—C25A—C20A | 120.18 (17) | O7—C27—H273 | 109.5 |
C24A—C25A—H25A | 119.9 | H271—C27—H272 | 109.5 |
O2A—C26A—H261 | 109.5 | H271—C27—H273 | 109.5 |
O2A—C26A—H263 | 109.5 | H272—C27—H273 | 109.5 |
O2A—C26A—H262 | 109.5 | O8—C28—H281 | 109.5 |
H261—C26A—H262 | 109.5 | O8—C28—H282 | 109.5 |
H261—C26A—H263 | 109.5 | O8—C28—H283 | 109.5 |
H263—C26A—H262 | 109.5 | H281—C28—H282 | 109.5 |
C1B—O1B—C5B | 114.55 (11) | H281—C28—H283 | 109.5 |
C1B—O2B—C26B | 112.38 (14) | H282—C28—H283 | 109.5 |
C2B—O3B—H32 | 106.1 (16) | O9—C29—H291 | 109.5 |
C3B—O4B—H42 | 104.3 (17) | O9—C29—H292 | 109.5 |
C4B—O5B—H52 | 110.0 (19) | O9—C29—H293 | 109.5 |
C6B—O6B—C7B | 117.24 (10) | H291—C29—H292 | 109.5 |
O1B—C1B—C2B | 110.24 (12) | H291—C29—H293 | 109.5 |
O1B—C1B—H1B | 108.4 | H292—C29—H293 | 109.5 |
O2B—C1B—O1B | 111.98 (12) | O10—C30—H301 | 109.5 |
O2B—C1B—C2B | 109.19 (13) | O10—C30—H302 | 109.5 |
O2B—C1B—H1B | 108.4 | O10—C30—H303 | 109.5 |
C2B—C1B—H1B | 108.4 | H301—C30—H302 | 109.5 |
O3B—C2B—C1B | 108.99 (13) | H301—C30—H303 | 109.5 |
O3B—C2B—C3B | 112.72 (13) | H302—C30—H303 | 109.5 |
C5A—O1A—C1A—O2A | 60.07 (16) | C5B—O1B—C1B—O2B | 62.92 (16) |
C5A—O1A—C1A—C2A | −61.44 (16) | C5B—O1B—C1B—C2B | −58.85 (16) |
C1A—O1A—C5A—C4A | 61.81 (16) | C1B—O1B—C5B—C4B | 59.91 (15) |
C1A—O1A—C5A—C6A | −178.11 (13) | C1B—O1B—C5B—C6B | −177.62 (12) |
C7A—O6A—C6A—C5A | −167.89 (12) | C7B—O6B—C6B—C5B | 168.28 (11) |
C6A—O6A—C7A—C8A | −53.73 (15) | C6B—O6B—C7B—C8B | 167.83 (11) |
C6A—O6A—C7A—C14A | −173.89 (11) | C6B—O6B—C7B—C14B | −79.14 (14) |
C6A—O6A—C7A—C20A | 72.73 (15) | C6B—O6B—C7B—C20B | 47.50 (15) |
O1A—C1A—O2A—C26A | 62.37 (17) | O1B—C1B—O2B—C26B | 65.80 (17) |
C2A—C1A—O2A—C26A | −175.89 (14) | C2B—C1B—O2B—C26B | −171.82 (14) |
O1A—C1A—C2A—O3A | 177.58 (12) | O2B—C1B—C2B—O3B | 55.92 (16) |
O1A—C1A—C2A—C3A | 54.39 (17) | O1B—C1B—C2B—O3B | 179.34 (12) |
O2A—C1A—C2A—O3A | 54.24 (16) | O2B—C1B—C2B—C3B | −69.41 (15) |
O2A—C1A—C2A—C3A | −68.95 (16) | O1B—C1B—C2B—C3B | 54.00 (16) |
O3A—C2A—C3A—O4A | 66.55 (16) | O3B—C2B—C3B—O4B | 64.53 (16) |
O3A—C2A—C3A—C4A | −172.44 (13) | O3B—C2B—C3B—C4B | −174.97 (13) |
C1A—C2A—C3A—O4A | −171.50 (13) | C1B—C2B—C3B—O4B | −172.22 (12) |
C1A—C2A—C3A—C4A | −50.49 (17) | C1B—C2B—C3B—C4B | −51.71 (16) |
O4A—C3A—C4A—O5A | −71.51 (16) | O4B—C3B—C4B—O5B | −70.07 (15) |
O4A—C3A—C4A—C5A | 168.67 (12) | O4B—C3B—C4B—C5B | 170.22 (12) |
C2A—C3A—C4A—O5A | 170.16 (13) | C2B—C3B—C4B—O5B | 171.88 (12) |
C2A—C3A—C4A—C5A | 50.34 (17) | C2B—C3B—C4B—C5B | 52.17 (15) |
O5A—C4A—C5A—O1A | −174.91 (12) | O5B—C4B—C5B—O1B | −175.70 (11) |
O5A—C4A—C5A—C6A | 67.18 (16) | O5B—C4B—C5B—C6B | 65.41 (15) |
C3A—C4A—C5A—O1A | −54.15 (16) | C3B—C4B—C5B—O1B | −55.10 (14) |
C3A—C4A—C5A—C6A | −172.05 (13) | C3B—C4B—C5B—C6B | −173.99 (12) |
O1A—C5A—C6A—O6A | 68.42 (15) | O1B—C5B—C6B—O6B | −70.33 (14) |
C4A—C5A—C6A—O6A | −172.14 (12) | C4B—C5B—C6B—O6B | 50.52 (16) |
O6A—C7A—C8A—C9A | 96.59 (16) | O6B—C7B—C8B—C9B | 27.35 (18) |
O6A—C7A—C8A—C13A | −72.94 (16) | O6B—C7B—C8B—C13B | −157.16 (14) |
C14A—C7A—C8A—C9A | −147.85 (14) | C14B—C7B—C8B—C9B | −88.66 (17) |
C14A—C7A—C8A—C13A | 42.63 (18) | C14B—C7B—C8B—C13B | 86.84 (17) |
C20A—C7A—C8A—C9A | −26.9 (2) | C20B—C7B—C8B—C9B | 144.39 (14) |
C20A—C7A—C8A—C13A | 163.62 (13) | C20B—C7B—C8B—C13B | −40.12 (19) |
O6A—C7A—C14A—C15A | −23.67 (18) | O6B—C7B—C14B—C15B | −10.25 (17) |
O6A—C7A—C14A—C19A | 161.74 (14) | O6B—C7B—C14B—C19B | 175.57 (13) |
C8A—C7A—C14A—C15A | −140.52 (15) | C8B—C7B—C14B—C15B | 101.71 (15) |
C8A—C7A—C14A—C19A | 44.89 (19) | C8B—C7B—C14B—C19B | −72.47 (16) |
C20A—C7A—C14A—C15A | 93.02 (16) | C20B—C7B—C14B—C15B | −132.76 (14) |
C20A—C7A—C14A—C19A | −81.57 (17) | C20B—C7B—C14B—C19B | 53.06 (18) |
O6A—C7A—C20A—C21A | −168.10 (13) | O6B—C7B—C20B—C21B | −103.70 (17) |
O6A—C7A—C20A—C25A | 18.56 (17) | O6B—C7B—C20B—C25B | 67.09 (16) |
C8A—C7A—C20A—C21A | −46.12 (18) | C8B—C7B—C20B—C21B | 141.61 (16) |
C8A—C7A—C20A—C25A | 140.54 (14) | C8B—C7B—C20B—C25B | −47.60 (18) |
C14A—C7A—C20A—C21A | 78.59 (16) | C14B—C7B—C20B—C21B | 19.8 (2) |
C14A—C7A—C20A—C25A | −94.76 (15) | C14B—C7B—C20B—C25B | −169.38 (13) |
C7A—C8A—C9A—C10A | −168.77 (15) | C7B—C8B—C9B—C10B | 175.70 (15) |
C13A—C8A—C9A—C10A | 0.9 (2) | C13B—C8B—C9B—C10B | 0.1 (3) |
C7A—C8A—C13A—C12A | 169.03 (15) | C7B—C8B—C13B—C12B | −174.68 (16) |
C9A—C8A—C13A—C12A | −1.0 (2) | C9B—C8B—C13B—C12B | 0.9 (3) |
C8A—C9A—C10A—C11A | 0.0 (3) | C8B—C9B—C10B—C11B | −1.0 (3) |
C9A—C10A—C11A—C12A | −0.7 (3) | C9B—C10B—C11B—C12B | 1.0 (3) |
C10A—C11A—C12A—C13A | 0.6 (3) | C10B—C11B—C12B—C13B | 0.0 (3) |
C11A—C12A—C13A—C8A | 0.2 (3) | C11B—C12B—C13B—C8B | −0.9 (3) |
C7A—C14A—C15A—C16A | −174.47 (15) | C7B—C14B—C15B—C16B | −175.31 (14) |
C19A—C14A—C15A—C16A | 0.2 (3) | C19B—C14B—C15B—C16B | −1.0 (2) |
C7A—C14A—C19A—C18A | 173.60 (17) | C7B—C14B—C19B—C18B | 174.75 (15) |
C15A—C14A—C19A—C18A | −1.1 (3) | C15B—C14B—C19B—C18B | 0.4 (2) |
C14A—C15A—C16A—C17A | 0.9 (3) | C14B—C15B—C16B—C17B | 0.6 (3) |
C15A—C16A—C17A—C18A | −1.3 (3) | C15B—C16B—C17B—C18B | 0.2 (3) |
C16A—C17A—C18A—C19A | 0.4 (3) | C16B—C17B—C18B—C19B | −0.7 (3) |
C17A—C18A—C19A—C14A | 0.8 (3) | C17B—C18B—C19B—C14B | 0.4 (3) |
C7A—C20A—C21A—C22A | −174.82 (15) | C7B—C20B—C21B—C22B | 170.08 (16) |
C25A—C20A—C21A—C22A | −1.4 (2) | C25B—C20B—C21B—C22B | −0.8 (3) |
C7A—C20A—C25A—C24A | 175.73 (15) | C7B—C20B—C25B—C24B | −170.56 (17) |
C21A—C20A—C25A—C24A | 2.2 (2) | C21B—C20B—C25B—C24B | 0.8 (3) |
C21A—C22A—C23A—C24A | 1.6 (3) | C20B—C21B—C22B—C23B | 0.4 (3) |
C20A—C21A—C22A—C23A | −0.5 (3) | C21B—C22B—C23B—C24B | 0.1 (3) |
C22A—C23A—C24A—C25A | −0.8 (3) | C22B—C23B—C24B—C25B | −0.1 (3) |
C23A—C24A—C25A—C20A | −1.1 (3) | C23B—C24B—C25B—C20B | −0.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3A—H31···O10 | 0.84 (3) | 1.88 (3) | 2.707 (2) | 169 (2) |
O3B—H32···O7 | 0.82 (3) | 1.91 (3) | 2.713 (2) | 165 (3) |
O4A—H41···O2B | 0.83 (3) | 2.02 (2) | 2.8287 (18) | 164.5 (19) |
O4B—H42···O2Ai | 0.77 (3) | 2.15 (3) | 2.9046 (19) | 166 (3) |
O5A—H51···O8 | 0.79 (3) | 1.87 (3) | 2.667 (2) | 175 (4) |
O5B—H52···O9i | 0.81 (4) | 1.90 (4) | 2.704 (2) | 173 (3) |
O7—H71···O5Ai | 0.79 (2) | 1.98 (2) | 2.763 (2) | 170 (3) |
O8—H81···O3B | 0.90 (3) | 1.84 (3) | 2.727 (2) | 170 (3) |
O9—H91···O3A | 0.85 (4) | 1.91 (4) | 2.741 (2) | 167 (4) |
O10—H101···O5B | 0.81 (3) | 1.95 (3) | 2.754 (2) | 170 (3) |
C1B—H1B···O3Aii | 0.98 | 2.32 | 3.2469 (19) | 157 |
C3A—H3A···O4Biii | 0.98 | 2.59 | 3.471 (2) | 149 |
C3B—H3B···O4A | 0.98 | 2.49 | 3.391 (2) | 153 |
C15B—H15B···O1B | 0.93 | 2.52 | 3.417 (2) | 161 |
C25A—H25A···O1A | 0.93 | 2.60 | 3.443 (2) | 151 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3A—H31···O10 | 0.84 (3) | 1.88 (3) | 2.707 (2) | 169 (2) |
O3B—H32···O7 | 0.82 (3) | 1.91 (3) | 2.713 (2) | 165 (3) |
O4A—H41···O2B | 0.83 (3) | 2.02 (2) | 2.8287 (18) | 164.5 (19) |
O4B—H42···O2Ai | 0.77 (3) | 2.15 (3) | 2.9046 (19) | 166 (3) |
O5A—H51···O8 | 0.79 (3) | 1.87 (3) | 2.667 (2) | 175 (4) |
O5B—H52···O9i | 0.81 (4) | 1.90 (4) | 2.704 (2) | 173 (3) |
O7—H71···O5Ai | 0.79 (2) | 1.98 (2) | 2.763 (2) | 170 (3) |
O8—H81···O3B | 0.90 (3) | 1.84 (3) | 2.727 (2) | 170 (3) |
O9—H91···O3A | 0.85 (4) | 1.91 (4) | 2.741 (2) | 167 (4) |
O10—H101···O5B | 0.81 (3) | 1.95 (3) | 2.754 (2) | 170 (3) |
C1B—H1B···O3Aii | 0.98 | 2.32 | 3.2469 (19) | 157.00 |
C3A—H3A···O4Biii | 0.98 | 2.59 | 3.471 (2) | 149.00 |
C3B—H3B···O4A | 0.98 | 2.49 | 3.391 (2) | 153.00 |
C15B—H15B···O1B | 0.93 | 2.52 | 3.417 (2) | 161.00 |
C25A—H25A···O1A | 0.93 | 2.60 | 3.443 (2) | 151.00 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) x+1, y, z. |
Acknowledgements
The authors wish to acknowledge the financial support of this work by Çankırı Karatekin University Research Fund (grant No. BAP: 2011/06) and thank Professor Volker Jäger of Stuttgart University, Germany, for helpful discussions.
References
Bernet, B. & Vasella, A. (1979). Helv. Chim. Acta, 62, 2401–2410. Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Dransfield, P. J., Moutel, S., Shipman, M. & Sik, V. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 3349–3335. Web of Science CrossRef Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gallos, J. K., Koumbis, A. E., Xiraphaki, V. P., Dellios, C. C. & Coutouli-Argyropoulou, E. (1999). Tetrahedron, 55, 15167–15180. Web of Science CrossRef CAS Google Scholar
Horton, D. & Lauterback, J. H. (1969). J. Org. Chem. pp. 86–92. CrossRef Web of Science Google Scholar
Kleban, M., Hilgers, P., Greul, J. N., Kugler, R. D., Li, J., Picasso, S., Vogel, P. & Jäger, V. (2001). Chembiochem, pp. 365–368. Web of Science CrossRef Google Scholar
Kobayashi, Y., Miyazaki, H. & Shiozaki, M. (1994). J. Org. Chem. 59, 813–822. CrossRef CAS Web of Science Google Scholar
Komiotis, D., Agelis, G., Manta, S., Tzioumaki, N. & Tsoukala, E. (2006). J. Carbohydr. Chem. 25, 441–450. Web of Science CrossRef CAS Google Scholar
Lopez, M., Trajkovic, J., Bornaghi, L., Innocenti, A., Vullo, D., Supuran, C. T. & Poulsen, S. A. (2011). J. Med. Chem. 54, 1481–1489. Web of Science CrossRef CAS PubMed Google Scholar
Peri, F., Deutman, A., Ferla, B. L. & Nicotra, F. (2002). Chem. Commun. pp. 1504–1505. Web of Science CrossRef Google Scholar
Peri, F., Jiménez-Barbero, J., Garcia-Aparicio, V., Travoška, I. & Nicotra, F. (2004). Eur. J. Chem. 10, 1433–1444. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The intramolecular 1,3-dipolar cycloadditions of various carbohydrates have been reported by several authors (Kobayashi et al., 1994; Kleban et al., 2001; Dransfield et al., 1999; Gallos et al., 1999). 1,3-Dipolar cycloadducts of various carbohdrates were converted into the amino (hydroxymethyl) cyclopentanetriols which are useful for glycosidase inhibitors (Kleban et al., 2001). The title compound is useful for the preparation of di- and trisaccharide analogues after several steps (Peri et al., 2002, 2004; Lopez et al., 2011), and it can be easily converted to the alkyl-5-enyl aldehydes. These aldehydes are useful intermediates for the syntheses of bicyclo[x.3.0] or bicyclo[x.2.1] derivatives after 1,3-dipolar cycloadditions (Dransfield et al., 1999). The present study was undertaken to ascertain the crystal structure of the title compound.
The asymmetric unit of the title compound contains two crystallographically independent molecules and four methanol solvent molecules (Fig. 1). The methyl α-D-glucopyranoside rings [A (O1a/C1a–C5a) and A' (O1b/C1b–C5b)] are in chair conformations with puckering parameters (Cremer & Pople, 1975) of QT = 0.551 (2)Å, ϕ = -5.8(2.5)°, θ = 4.4 (2)° and QT = 0.550 (2)Å, ϕ = -40.7(4.9)°, θ = 2.0 (2)°, respectively. In trityl cation, the rings B (C8a–C13a), C (C14a–C19a), D (C20a–C25a) and B' (C8b–C13b), C' (C14b–C19b), D'(C20b–C25b) are oriented at dihedral angles of A/B = 74.16 (6), A/C = 63.29 (7), B/C = 83.19 (6) ° and A'/B' = 82.73 (6), A'/C' = 73.69 (7), B'/C' = 65.34 (6) °, respectively. The intramolecular O—H···O and C—H···O hydrogen bonds (Table 1) link the molecules in the asymmetric unit.
In the crystal structure, intra- and intermolecular O-H···O and C-H···O hydrogen bonds (Table 1, Fig. 2) link the molecules into a three-dimensional structure.