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The crystal structures of 1,2,3,4,6-penta-O-acetyl-α-D-manno­pyran­ose, C16H22O11, and 2,3,4,6-tetra-O-acetyl-α-D-manno­pyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-manno­pyranosyl-(1→3)-1,2,4,6-tetra-O-acetyl-α-D-manno­pyran­ose, C40H54O27, were determined and compared to those of methyl 2,3,4,6-tetra-O-acetyl-α-D-manno­pyran­oside, methyl α-D-manno­pyran­oside and methyl α-D-manno­pyranosyl-(1→2)-α-D-manno­pyran­oside to evaluate the effects of O-acetyl­ation on bond lengths, bond angles and torsion angles. In general, O-acetyl­ation exerts little effect on the exo- and endocyclic C—C and endocyclic C—O bond lengths, but the exocyclic C—O bonds involved in O-acetyl­ation are lengthened by ∼0.02 Å. The conformation of the O-acetyl side-chains is highly conserved, with the carbonyl O atom either eclipsing the H atom attached to a 2°-alcoholic C atom or bis­ecting the H—C—H bond angle of a 1°-alcoholic C atom. Of the two C—O bonds that determine O-acetyl side-chain conformation, that involving the alcoholic C atom exhibits greater rotational variability than that involving the carbonyl C atom. These findings are in good agreement with recent solution NMR studies of O-acetyl side-chain conformations in saccharides. Experimental evidence was also obtained to confirm density functional theory (DFT) predictions of C—O and O—H bond-length behavior in a C—O—H fragment involved in hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619008817/fp3073sup1.cif
Contains datablocks I, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008817/fp3073Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008817/fp3073IIIsup3.hkl
Contains datablock III

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619008817/fp3073sup4.pdf
NMR spectra for (III)

CCDC references: 1935527; 1935526

Computing details top

For both structures, data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2015a) for (I); SHELXT (Sheldrick, 2015a) for (III). For both structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

1,2,3,4,6-Penta-O-acetyl-α-D-mannopyranose (I) top
Crystal data top
C16H22O11Dx = 1.344 Mg m3
Mr = 390.33Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 9740 reflections
a = 8.8434 (4) Åθ = 3.6–71.7°
b = 15.1918 (6) ŵ = 1.00 mm1
c = 43.0639 (17) ÅT = 120 K
V = 5785.5 (4) Å3Needle, clear colourless
Z = 120.17 × 0.05 × 0.02 mm
F(000) = 2472
Data collection top
Bruker APEXII CCD
diffractometer
11335 independent reflections
Radiation source: Incoatec micro-focus10694 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm-1Rint = 0.046
φ and ω scansθmax = 72.0°, θmin = 2.1°
Absorption correction: numerical
(SADABS; Krause et al., 2015)
h = 1010
Tmin = 0.692, Tmax = 0.939k = 1818
78838 measured reflectionsl = 5253
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0764P)2 + 0.596P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.030
11335 reflectionsΔρmax = 0.45 e Å3
754 parametersΔρmin = 0.25 e Å3
6 restraintsAbsolute structure: Flack x determined using 4495 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (4)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.9767 (2)0.00373 (13)0.86654 (5)0.0373 (4)
O20.7275 (2)0.16020 (14)0.83026 (4)0.0354 (4)
O30.9626 (2)0.27328 (13)0.84368 (4)0.0313 (4)
O40.9383 (2)0.26391 (12)0.91044 (4)0.0284 (3)
O50.7509 (2)0.06018 (13)0.88578 (4)0.0340 (4)
O60.6934 (2)0.05736 (13)0.94909 (4)0.0352 (4)
O70.8723 (3)0.13120 (17)0.87041 (7)0.0633 (7)
O80.8086 (3)0.16490 (18)0.78083 (5)0.0500 (5)
O91.1672 (2)0.21730 (17)0.81960 (5)0.0429 (5)
O100.7728 (2)0.37476 (12)0.90327 (5)0.0329 (4)
O110.5252 (2)0.12778 (15)0.97930 (4)0.0392 (4)
C10.8326 (3)0.0412 (2)0.85888 (6)0.0358 (6)
H10.7740700.0009800.8457050.043*
C20.8690 (3)0.12350 (18)0.84016 (6)0.0319 (5)
H20.9329300.1082140.8217840.038*
C30.9490 (3)0.19183 (17)0.86044 (5)0.0281 (5)
H31.0513070.1699290.8666140.034*
C40.8535 (3)0.20927 (17)0.88918 (5)0.0273 (5)
H40.7564230.2386770.8833130.033*
C50.8219 (3)0.12249 (17)0.90626 (6)0.0285 (5)
H50.9181130.0975480.9147320.034*
C60.7110 (3)0.13890 (18)0.93223 (6)0.0311 (5)
H6A0.7494000.1855600.9462030.037*
H6B0.6124350.1581160.9236750.037*
C70.9792 (4)0.0839 (2)0.87404 (7)0.0448 (7)
C81.1298 (5)0.1089 (2)0.88671 (9)0.0553 (8)
H8A1.2062760.1037000.8703520.083*
H8B1.1263260.1698510.8941610.083*
H8C1.1558670.0697100.9039680.083*
C90.7113 (3)0.17773 (19)0.79951 (6)0.0356 (6)
C100.5576 (3)0.2142 (2)0.79296 (7)0.0421 (6)
H10D0.4872870.1658030.7887710.063*
H10E0.5625410.2530630.7748210.063*
H10F0.5222290.2477330.8110000.063*
C111.0754 (3)0.2756 (2)0.82214 (6)0.0347 (6)
C121.0653 (3)0.3563 (2)0.80258 (7)0.0444 (7)
H12D0.9729120.3541070.7900380.067*
H12E1.1535510.3594630.7888590.067*
H12F1.0628180.4084200.8159800.067*
C130.8819 (3)0.34529 (16)0.91630 (5)0.0253 (4)
C140.9733 (3)0.39184 (18)0.94041 (6)0.0323 (5)
H14D0.9946740.3514680.9576030.049*
H14E0.9165080.4426540.9481930.049*
H14F1.0686570.4119450.9312400.049*
C150.5985 (3)0.0631 (2)0.97333 (6)0.0354 (6)
C160.5976 (4)0.0210 (2)0.99180 (8)0.0494 (8)
H16D0.6253410.0702930.9782700.074*
H16E0.4962330.0309401.0003000.074*
H16F0.6705980.0165111.0088420.074*
O1'0.5508 (2)0.77458 (17)0.86961 (5)0.0429 (5)
O2'0.6585 (2)0.70816 (13)0.79238 (4)0.0317 (4)
O3'0.5477 (2)0.87430 (13)0.77922 (4)0.0372 (4)
O4'0.2354 (2)0.85397 (12)0.80419 (4)0.0302 (4)
O5'0.4374 (2)0.66848 (12)0.83775 (4)0.0306 (4)
O6'0.1257 (2)0.62495 (14)0.84823 (4)0.0350 (4)
O7'0.6885 (4)0.6944 (2)0.90233 (6)0.0670 (8)
O8'0.8780 (2)0.77943 (16)0.78301 (6)0.0481 (5)
O9'0.5090 (12)1.0047 (3)0.80002 (15)0.082 (2)0.5
O9'A0.6386 (11)0.9883 (4)0.80298 (11)0.073 (2)0.5
O10'0.2298 (3)0.86657 (17)0.75210 (5)0.0488 (5)
O11'0.0852 (3)0.5949 (2)0.82206 (6)0.0630 (8)
C1'0.5725 (3)0.7125 (2)0.84450 (6)0.0355 (6)
H1'0.6523030.6688840.8503230.043*
C2'0.6271 (3)0.76826 (19)0.81744 (6)0.0327 (5)
H2'0.7211250.8007440.8233670.039*
C3'0.5046 (3)0.83272 (17)0.80802 (6)0.0304 (5)
H3'0.4941860.8787350.8244880.037*
C4'0.3527 (3)0.78810 (16)0.80318 (6)0.0269 (5)
H4'0.3507020.7559040.7829270.032*
C5'0.3137 (3)0.72593 (17)0.83007 (5)0.0276 (5)
H5'0.2854800.7614060.8487490.033*
C6'0.1825 (3)0.66883 (18)0.82081 (6)0.0316 (5)
H6'A0.1017850.7053090.8114140.038*
H6'B0.2154600.6247550.8052950.038*
C7'0.6210 (5)0.7594 (3)0.89692 (7)0.0528 (9)
C8'0.5978 (6)0.8342 (3)0.91894 (8)0.0713 (13)
H8'A0.6374140.8884690.9097150.107*
H8'B0.6511340.8220220.9384130.107*
H8'C0.4894960.8411800.9231320.107*
C9'0.7929 (3)0.72002 (19)0.77746 (6)0.0338 (5)
C10'0.8177 (3)0.6495 (2)0.75383 (6)0.0398 (6)
H10A0.7857080.5927130.7623580.060*
H10B0.9253220.6469010.7484450.060*
H10C0.7585140.6627410.7351640.060*
C11'0.5809 (6)0.9573 (2)0.77935 (7)0.0571 (10)
C12'0.6175 (5)0.9932 (2)0.74801 (6)0.0468 (7)
H12A0.6278870.9446120.7331970.070*
H12B0.7126451.0261730.7490150.070*
H12C0.5360491.0324920.7412110.070*
C13'0.1829 (3)0.88749 (18)0.77697 (7)0.0342 (5)
C14'0.0634 (4)0.9549 (2)0.78346 (8)0.0423 (6)
H14A0.0160830.9286790.7963410.064*
H14B0.0196140.9752940.7638320.064*
H14C0.1084611.0049200.7944730.064*
C15'0.0117 (3)0.5882 (2)0.84508 (7)0.0408 (7)
C16'0.0578 (4)0.5371 (3)0.87305 (9)0.0655 (12)
H16A0.0302240.5279990.8864930.098*
H16B0.0983960.4798850.8666110.098*
H16C0.1356310.5697340.8844400.098*
O1"0.50928 (19)0.47554 (12)0.86740 (4)0.0269 (3)
O2"0.25074 (19)0.56673 (11)0.92338 (4)0.0287 (3)
O3"0.4895 (2)0.55590 (14)0.96268 (4)0.0356 (4)
O4"0.54649 (19)0.37000 (13)0.96282 (4)0.0292 (4)
O5"0.31376 (19)0.40220 (11)0.89322 (4)0.0256 (3)
O6"0.3832 (2)0.21389 (12)0.89309 (4)0.0299 (4)
O7"0.3793 (3)0.43791 (19)0.82464 (5)0.0502 (6)
O8"0.3069 (3)0.71143 (15)0.92369 (7)0.0584 (7)
O9"0.7442 (3)0.55746 (18)0.96681 (6)0.0531 (6)
O10"0.3819 (3)0.3575 (2)1.00200 (5)0.0553 (7)
O11"0.2509 (3)0.10262 (15)0.91357 (5)0.0481 (5)
C1"0.3679 (3)0.48445 (16)0.88336 (5)0.0264 (5)
H1"0.2921660.5119280.8690940.032*
C2"0.3979 (3)0.54644 (16)0.91045 (6)0.0273 (5)
H2"0.4483610.6013930.9029670.033*
C3"0.4943 (3)0.50176 (17)0.93516 (5)0.0272 (5)
H3"0.6009190.4966050.9276670.033*
C4"0.4337 (3)0.41107 (17)0.94344 (5)0.0260 (5)
H4"0.3353710.4160760.9547730.031*
C5"0.4147 (3)0.35635 (16)0.91387 (5)0.0251 (5)
H5"0.5152270.3488090.9035820.030*
C6"0.3453 (3)0.26701 (16)0.91980 (5)0.0272 (5)
H6"A0.3872630.2406850.9389840.033*
H6"B0.2341730.2719600.9220670.033*
C7"0.4974 (3)0.44895 (19)0.83724 (6)0.0335 (5)
C8"0.6514 (3)0.4363 (2)0.82323 (6)0.0405 (6)
H8"A0.7036630.4930940.8221930.061*
H8"B0.6410030.4120300.8022530.061*
H8"C0.7099910.3954860.8361090.061*
C9"0.2192 (3)0.65288 (18)0.92846 (7)0.0350 (6)
C10"0.0619 (4)0.6648 (2)0.94069 (8)0.0451 (7)
H10G0.0134540.6071500.9429860.068*
H10H0.0033760.7008740.9261480.068*
H10I0.0659970.6941730.9609340.068*
C11"0.6224 (4)0.5788 (2)0.97605 (8)0.0480 (7)
C12"0.5907 (6)0.6325 (5)1.00451 (14)0.106 (2)
H12G0.5229230.6812460.9991590.159*
H12H0.6857960.6561051.0127100.159*
H12I0.5426620.5953131.0202670.159*
C13"0.5084 (3)0.35107 (18)0.99243 (6)0.0310 (5)
C14"0.6434 (3)0.3206 (2)1.01054 (6)0.0372 (6)
H14G0.6702010.2606691.0041410.056*
H14H0.6194030.3210261.0327560.056*
H14I0.7287950.3601001.0065580.056*
C15"0.3287 (3)0.13076 (18)0.89315 (6)0.0313 (5)
C16"0.3787 (3)0.08173 (19)0.86474 (7)0.0376 (6)
H16G0.2961770.0805990.8495670.056*
H16H0.4059150.0213150.8704420.056*
H16I0.4667740.1112220.8556480.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0384 (10)0.0295 (9)0.0440 (10)0.0014 (8)0.0122 (8)0.0054 (8)
O20.0282 (9)0.0507 (11)0.0273 (9)0.0038 (8)0.0015 (7)0.0084 (8)
O30.0292 (9)0.0381 (10)0.0266 (8)0.0031 (7)0.0026 (7)0.0001 (7)
O40.0253 (8)0.0339 (9)0.0260 (8)0.0032 (7)0.0030 (6)0.0050 (7)
O50.0298 (9)0.0414 (10)0.0307 (9)0.0081 (8)0.0067 (7)0.0084 (8)
O60.0382 (10)0.0384 (10)0.0292 (9)0.0003 (8)0.0090 (7)0.0010 (7)
O70.0706 (17)0.0417 (13)0.0775 (17)0.0180 (12)0.0127 (14)0.0039 (12)
O80.0511 (12)0.0631 (14)0.0359 (10)0.0032 (11)0.0144 (10)0.0094 (10)
O90.0314 (10)0.0617 (13)0.0357 (10)0.0003 (9)0.0081 (8)0.0013 (9)
O100.0248 (8)0.0341 (9)0.0399 (10)0.0010 (7)0.0028 (7)0.0010 (7)
O110.0344 (10)0.0509 (12)0.0323 (9)0.0028 (9)0.0085 (8)0.0026 (8)
C10.0346 (13)0.0409 (14)0.0318 (13)0.0078 (11)0.0071 (10)0.0103 (11)
C20.0267 (11)0.0417 (14)0.0272 (11)0.0029 (10)0.0043 (9)0.0079 (10)
C30.0250 (11)0.0340 (12)0.0252 (10)0.0008 (9)0.0021 (9)0.0048 (9)
C40.0244 (11)0.0349 (12)0.0225 (10)0.0004 (9)0.0002 (8)0.0047 (9)
C50.0246 (11)0.0338 (12)0.0270 (11)0.0003 (9)0.0013 (9)0.0044 (9)
C60.0292 (12)0.0373 (13)0.0270 (11)0.0041 (10)0.0049 (9)0.0001 (10)
C70.0559 (18)0.0343 (14)0.0442 (16)0.0040 (13)0.0194 (14)0.0048 (12)
C80.065 (2)0.0384 (16)0.063 (2)0.0113 (15)0.0145 (17)0.0056 (14)
C90.0402 (14)0.0365 (13)0.0301 (12)0.0117 (11)0.0049 (11)0.0029 (10)
C100.0399 (15)0.0477 (16)0.0389 (14)0.0107 (13)0.0049 (11)0.0005 (12)
C110.0278 (12)0.0500 (16)0.0265 (11)0.0085 (11)0.0007 (9)0.0033 (11)
C120.0369 (14)0.0595 (19)0.0367 (14)0.0118 (13)0.0005 (11)0.0093 (13)
C130.0220 (10)0.0310 (12)0.0228 (10)0.0007 (9)0.0039 (8)0.0021 (8)
C140.0319 (12)0.0347 (13)0.0305 (12)0.0004 (10)0.0030 (10)0.0030 (10)
C150.0332 (13)0.0439 (15)0.0289 (12)0.0084 (11)0.0029 (10)0.0033 (11)
C160.061 (2)0.0432 (17)0.0437 (16)0.0075 (14)0.0148 (15)0.0015 (13)
O1'0.0362 (10)0.0635 (14)0.0290 (9)0.0090 (10)0.0000 (8)0.0081 (9)
O2'0.0252 (8)0.0383 (10)0.0318 (9)0.0027 (7)0.0029 (7)0.0037 (7)
O3'0.0470 (11)0.0334 (9)0.0312 (9)0.0094 (8)0.0154 (8)0.0059 (8)
O4'0.0308 (8)0.0286 (8)0.0312 (9)0.0022 (7)0.0074 (7)0.0004 (7)
O5'0.0245 (8)0.0347 (9)0.0325 (9)0.0004 (7)0.0011 (7)0.0032 (7)
O6'0.0248 (8)0.0439 (10)0.0363 (9)0.0062 (8)0.0043 (7)0.0137 (8)
O7'0.0810 (19)0.0656 (18)0.0544 (15)0.0216 (15)0.0280 (14)0.0111 (13)
O8'0.0376 (11)0.0500 (12)0.0568 (13)0.0117 (10)0.0170 (10)0.0063 (10)
O9'0.166 (8)0.025 (2)0.053 (3)0.013 (4)0.050 (4)0.007 (2)
O9'A0.144 (6)0.050 (3)0.023 (2)0.054 (4)0.008 (3)0.0031 (19)
O10'0.0587 (13)0.0562 (13)0.0316 (10)0.0180 (11)0.0070 (9)0.0089 (9)
O11'0.0481 (13)0.0875 (19)0.0533 (13)0.0363 (13)0.0227 (11)0.0363 (13)
C1'0.0250 (12)0.0505 (16)0.0310 (12)0.0047 (11)0.0014 (9)0.0008 (11)
C2'0.0271 (11)0.0407 (14)0.0303 (12)0.0072 (10)0.0027 (10)0.0069 (10)
C3'0.0325 (12)0.0318 (12)0.0271 (11)0.0073 (10)0.0070 (9)0.0035 (9)
C4'0.0258 (11)0.0266 (11)0.0283 (11)0.0006 (9)0.0025 (9)0.0010 (9)
C5'0.0233 (10)0.0310 (12)0.0285 (11)0.0008 (9)0.0006 (9)0.0020 (9)
C6'0.0288 (12)0.0361 (13)0.0297 (12)0.0051 (10)0.0032 (10)0.0066 (10)
C7'0.061 (2)0.063 (2)0.0344 (15)0.0304 (18)0.0099 (14)0.0079 (14)
C8'0.086 (3)0.093 (3)0.0351 (16)0.047 (3)0.0007 (18)0.0128 (18)
C9'0.0287 (12)0.0402 (14)0.0325 (12)0.0023 (11)0.0025 (10)0.0044 (11)
C10'0.0362 (13)0.0508 (16)0.0324 (13)0.0057 (12)0.0031 (11)0.0015 (12)
C11'0.109 (3)0.0355 (15)0.0266 (13)0.0179 (18)0.0029 (16)0.0024 (12)
C12'0.071 (2)0.0417 (15)0.0272 (13)0.0109 (15)0.0044 (13)0.0010 (11)
C13'0.0355 (13)0.0302 (12)0.0369 (14)0.0009 (10)0.0056 (11)0.0061 (10)
C14'0.0432 (15)0.0327 (13)0.0512 (17)0.0071 (12)0.0077 (13)0.0085 (12)
C15'0.0303 (13)0.0478 (16)0.0443 (15)0.0107 (12)0.0085 (12)0.0172 (13)
C16'0.0458 (18)0.100 (3)0.0510 (19)0.035 (2)0.0163 (15)0.038 (2)
O1"0.0242 (8)0.0342 (9)0.0222 (8)0.0027 (6)0.0022 (6)0.0036 (6)
O2"0.0241 (8)0.0276 (8)0.0344 (8)0.0023 (7)0.0009 (7)0.0026 (7)
O3"0.0316 (9)0.0426 (10)0.0325 (9)0.0048 (8)0.0045 (7)0.0118 (8)
O4"0.0233 (8)0.0413 (10)0.0230 (8)0.0039 (7)0.0011 (6)0.0045 (7)
O5"0.0224 (7)0.0299 (8)0.0246 (8)0.0024 (6)0.0042 (6)0.0033 (6)
O6"0.0304 (8)0.0306 (9)0.0287 (8)0.0025 (7)0.0033 (7)0.0003 (7)
O7"0.0399 (11)0.0844 (17)0.0264 (9)0.0170 (12)0.0060 (8)0.0035 (10)
O8"0.0451 (12)0.0293 (10)0.101 (2)0.0015 (9)0.0163 (13)0.0031 (12)
O9"0.0357 (11)0.0617 (14)0.0619 (14)0.0011 (10)0.0137 (10)0.0217 (12)
O10"0.0381 (11)0.094 (2)0.0340 (10)0.0128 (12)0.0083 (9)0.0176 (11)
O11"0.0595 (14)0.0405 (11)0.0443 (11)0.0166 (10)0.0164 (10)0.0042 (9)
C1"0.0218 (10)0.0315 (12)0.0259 (11)0.0007 (9)0.0018 (9)0.0038 (9)
C2"0.0230 (11)0.0281 (11)0.0308 (11)0.0000 (9)0.0003 (9)0.0025 (9)
C3"0.0247 (11)0.0322 (12)0.0246 (11)0.0000 (9)0.0022 (9)0.0042 (9)
C4"0.0210 (10)0.0340 (12)0.0231 (10)0.0024 (9)0.0011 (8)0.0033 (9)
C5"0.0203 (10)0.0314 (12)0.0236 (10)0.0006 (8)0.0009 (8)0.0035 (9)
C6"0.0257 (11)0.0294 (12)0.0266 (11)0.0015 (9)0.0025 (9)0.0021 (9)
C7"0.0349 (13)0.0423 (14)0.0234 (11)0.0101 (11)0.0011 (10)0.0034 (10)
C8"0.0364 (15)0.0563 (17)0.0289 (12)0.0117 (12)0.0048 (11)0.0050 (12)
C9"0.0331 (13)0.0292 (12)0.0428 (14)0.0020 (10)0.0001 (10)0.0021 (10)
C10"0.0387 (15)0.0365 (14)0.0600 (19)0.0075 (12)0.0087 (13)0.0014 (13)
C11"0.0409 (16)0.0539 (18)0.0493 (17)0.0037 (14)0.0125 (14)0.0195 (14)
C12"0.073 (3)0.144 (5)0.101 (4)0.017 (3)0.026 (3)0.089 (4)
C13"0.0319 (12)0.0366 (13)0.0246 (11)0.0000 (10)0.0025 (9)0.0016 (9)
C14"0.0399 (15)0.0443 (15)0.0274 (12)0.0005 (12)0.0099 (11)0.0042 (10)
C15"0.0283 (12)0.0322 (12)0.0334 (12)0.0021 (10)0.0011 (10)0.0010 (10)
C16"0.0361 (13)0.0382 (14)0.0385 (14)0.0054 (11)0.0050 (11)0.0073 (11)
Geometric parameters (Å, º) top
O1—C71.370 (4)C4'—H4'1.0000
O1—C11.435 (4)C5'—C6'1.503 (3)
O2—C91.358 (3)C5'—H5'1.0000
O2—C21.435 (3)C6'—H6'A0.9900
O3—C111.363 (3)C6'—H6'B0.9900
O3—C31.438 (3)C7'—C8'1.494 (6)
O4—C131.357 (3)C8'—H8'A0.9800
O4—C41.446 (3)C8'—H8'B0.9800
O5—C11.395 (3)C8'—H8'C0.9800
O5—C51.438 (3)C9'—C10'1.494 (4)
O6—C151.342 (3)C10'—H10A0.9800
O6—C61.444 (3)C10'—H10B0.9800
O7—C71.198 (4)C10'—H10C0.9800
O8—C91.194 (4)C11'—C12'1.492 (4)
O9—C111.206 (4)C12'—H12A0.9800
O10—C131.202 (3)C12'—H12B0.9800
O11—C151.205 (4)C12'—H12C0.9800
C1—C21.522 (4)C13'—C14'1.498 (4)
C1—H11.0000C14'—H14A0.9800
C2—C31.530 (3)C14'—H14B0.9800
C2—H21.0000C14'—H14C0.9800
C3—C41.521 (3)C15'—C16'1.490 (4)
C3—H31.0000C16'—H16A0.9800
C4—C51.535 (4)C16'—H16B0.9800
C4—H41.0000C16'—H16C0.9800
C5—C61.508 (3)O1"—C7"1.364 (3)
C5—H51.0000O1"—C1"1.433 (3)
C6—H6A0.9900O2"—C9"1.356 (3)
C6—H6B0.9900O2"—C2"1.449 (3)
C7—C81.488 (5)O3"—C11"1.354 (4)
C8—H8A0.9800O3"—C3"1.443 (3)
C8—H8B0.9800O4"—C13"1.350 (3)
C8—H8C0.9800O4"—C4"1.442 (3)
C9—C101.494 (4)O5"—C1"1.404 (3)
C10—H10D0.9800O5"—C5"1.439 (3)
C10—H10E0.9800O6"—C15"1.352 (3)
C10—H10F0.9800O6"—C6"1.445 (3)
C11—C121.491 (4)O7"—C7"1.188 (4)
C12—H12D0.9800O8"—C9"1.198 (4)
C12—H12E0.9800O9"—C11"1.193 (4)
C12—H12F0.9800O10"—C13"1.196 (4)
C13—C141.494 (3)O11"—C15"1.196 (4)
C14—H14D0.9800C1"—C2"1.523 (3)
C14—H14E0.9800C1"—H1"1.0000
C14—H14F0.9800C2"—C3"1.523 (3)
C15—C161.505 (4)C2"—H2"1.0000
C16—H16D0.9800C3"—C4"1.520 (3)
C16—H16E0.9800C3"—H3"1.0000
C16—H16F0.9800C4"—C5"1.530 (3)
O1'—C7'1.349 (4)C4"—H4"1.0000
O1'—C1'1.448 (3)C5"—C6"1.512 (3)
O2'—C9'1.363 (3)C5"—H5"1.0000
O2'—C2'1.441 (3)C6"—H6"A0.9900
O3'—C11'1.294 (4)C6"—H6"B0.9900
O3'—C3'1.443 (3)C7"—C8"1.502 (4)
O4'—C13'1.360 (3)C8"—H8"A0.9800
O4'—C4'1.442 (3)C8"—H8"B0.9800
O5'—C1'1.399 (3)C8"—H8"C0.9800
O5'—C5'1.438 (3)C9"—C10"1.499 (4)
O6'—C15'1.344 (3)C10"—H10G0.9800
O6'—C6'1.446 (3)C10"—H10H0.9800
O7'—C7'1.178 (5)C10"—H10I0.9800
O8'—C9'1.199 (4)C11"—C12"1.499 (5)
O9'—C11'1.310 (7)C12"—H12G0.9800
O9'A—C11'1.232 (6)C12"—H12H0.9800
O10'—C13'1.192 (4)C12"—H12I0.9800
O11'—C15'1.190 (4)C13"—C14"1.499 (3)
C1'—C2'1.519 (4)C14"—H14G0.9800
C1'—H1'1.0000C14"—H14H0.9800
C2'—C3'1.516 (4)C14"—H14I0.9800
C2'—H2'1.0000C15"—C16"1.499 (4)
C3'—C4'1.519 (3)C16"—H16G0.9800
C3'—H3'1.0000C16"—H16H0.9800
C4'—C5'1.534 (3)C16"—H16I0.9800
C7—O1—C1117.0 (2)C7'—C8'—H8'A109.5
C9—O2—C2117.3 (2)C7'—C8'—H8'B109.5
C11—O3—C3115.1 (2)H8'A—C8'—H8'B109.5
C13—O4—C4116.72 (19)C7'—C8'—H8'C109.5
C1—O5—C5114.78 (19)H8'A—C8'—H8'C109.5
C15—O6—C6113.7 (2)H8'B—C8'—H8'C109.5
O5—C1—O1110.5 (2)O8'—C9'—O2'123.6 (3)
O5—C1—C2112.3 (2)O8'—C9'—C10'125.6 (3)
O1—C1—C2105.0 (2)O2'—C9'—C10'110.8 (2)
O5—C1—H1109.6C9'—C10'—H10A109.5
O1—C1—H1109.6C9'—C10'—H10B109.5
C2—C1—H1109.6H10A—C10'—H10B109.5
O2—C2—C1107.0 (2)C9'—C10'—H10C109.5
O2—C2—C3108.0 (2)H10A—C10'—H10C109.5
C1—C2—C3110.7 (2)H10B—C10'—H10C109.5
O2—C2—H2110.4O9'A—C11'—O3'118.0 (4)
C1—C2—H2110.4O3'—C11'—O9'115.4 (4)
C3—C2—H2110.4O9'A—C11'—C12'121.1 (4)
O3—C3—C4107.8 (2)O3'—C11'—C12'113.7 (3)
O3—C3—C2109.6 (2)O9'—C11'—C12'121.3 (4)
C4—C3—C2109.0 (2)C11'—C12'—H12A109.5
O3—C3—H3110.1C11'—C12'—H12B109.5
C4—C3—H3110.1H12A—C12'—H12B109.5
C2—C3—H3110.1C11'—C12'—H12C109.5
O4—C4—C3109.08 (19)H12A—C12'—H12C109.5
O4—C4—C5106.48 (19)H12B—C12'—H12C109.5
C3—C4—C5109.9 (2)O10'—C13'—O4'123.8 (3)
O4—C4—H4110.4O10'—C13'—C14'126.6 (3)
C3—C4—H4110.4O4'—C13'—C14'109.6 (2)
C5—C4—H4110.4C13'—C14'—H14A109.5
O5—C5—C6106.2 (2)C13'—C14'—H14B109.5
O5—C5—C4110.5 (2)H14A—C14'—H14B109.5
C6—C5—C4109.4 (2)C13'—C14'—H14C109.5
O5—C5—H5110.2H14A—C14'—H14C109.5
C6—C5—H5110.2H14B—C14'—H14C109.5
C4—C5—H5110.2O11'—C15'—O6'122.8 (3)
O6—C6—C5107.5 (2)O11'—C15'—C16'124.7 (3)
O6—C6—H6A110.2O6'—C15'—C16'112.5 (2)
C5—C6—H6A110.2C15'—C16'—H16A109.5
O6—C6—H6B110.2C15'—C16'—H16B109.5
C5—C6—H6B110.2H16A—C16'—H16B109.5
H6A—C6—H6B108.5C15'—C16'—H16C109.5
O7—C7—O1122.6 (4)H16A—C16'—H16C109.5
O7—C7—C8126.9 (3)H16B—C16'—H16C109.5
O1—C7—C8110.4 (3)C7"—O1"—C1"114.65 (19)
C7—C8—H8A109.5C9"—O2"—C2"116.9 (2)
C7—C8—H8B109.5C11"—O3"—C3"118.1 (2)
H8A—C8—H8B109.5C13"—O4"—C4"117.79 (19)
C7—C8—H8C109.5C1"—O5"—C5"113.96 (18)
H8A—C8—H8C109.5C15"—O6"—C6"115.95 (19)
H8B—C8—H8C109.5O5"—C1"—O1"111.01 (19)
O8—C9—O2123.3 (3)O5"—C1"—C2"112.22 (19)
O8—C9—C10126.1 (3)O1"—C1"—C2"105.89 (19)
O2—C9—C10110.7 (2)O5"—C1"—H1"109.2
C9—C10—H10D109.5O1"—C1"—H1"109.2
C9—C10—H10E109.5C2"—C1"—H1"109.2
H10D—C10—H10E109.5O2"—C2"—C1"105.65 (19)
C9—C10—H10F109.5O2"—C2"—C3"109.19 (19)
H10D—C10—H10F109.5C1"—C2"—C3"110.9 (2)
H10E—C10—H10F109.5O2"—C2"—H2"110.3
O9—C11—O3122.4 (3)C1"—C2"—H2"110.3
O9—C11—C12126.4 (3)C3"—C2"—H2"110.3
O3—C11—C12111.2 (3)O3"—C3"—C4"108.3 (2)
C11—C12—H12D109.5O3"—C3"—C2"107.7 (2)
C11—C12—H12E109.5C4"—C3"—C2"111.74 (19)
H12D—C12—H12E109.5O3"—C3"—H3"109.7
C11—C12—H12F109.5C4"—C3"—H3"109.7
H12D—C12—H12F109.5C2"—C3"—H3"109.7
H12E—C12—H12F109.5O4"—C4"—C3"106.50 (19)
O10—C13—O4123.2 (2)O4"—C4"—C5"108.81 (19)
O10—C13—C14125.6 (2)C3"—C4"—C5"109.63 (19)
O4—C13—C14111.2 (2)O4"—C4"—H4"110.6
C13—C14—H14D109.5C3"—C4"—H4"110.6
C13—C14—H14E109.5C5"—C4"—H4"110.6
H14D—C14—H14E109.5O5"—C5"—C6"106.69 (19)
C13—C14—H14F109.5O5"—C5"—C4"108.63 (19)
H14D—C14—H14F109.5C6"—C5"—C4"113.06 (19)
H14E—C14—H14F109.5O5"—C5"—H5"109.5
O11—C15—O6123.8 (3)C6"—C5"—H5"109.5
O11—C15—C16125.2 (3)C4"—C5"—H5"109.5
O6—C15—C16111.0 (3)O6"—C6"—C5"105.81 (18)
C15—C16—H16D109.5O6"—C6"—H6"A110.6
C15—C16—H16E109.5C5"—C6"—H6"A110.6
H16D—C16—H16E109.5O6"—C6"—H6"B110.6
C15—C16—H16F109.5C5"—C6"—H6"B110.6
H16D—C16—H16F109.5H6"A—C6"—H6"B108.7
H16E—C16—H16F109.5O7"—C7"—O1"123.0 (3)
C7'—O1'—C1'118.6 (3)O7"—C7"—C8"126.5 (2)
C9'—O2'—C2'115.9 (2)O1"—C7"—C8"110.5 (2)
C11'—O3'—C3'118.9 (2)C7"—C8"—H8"A109.5
C13'—O4'—C4'118.63 (19)C7"—C8"—H8"B109.5
C1'—O5'—C5'114.0 (2)H8"A—C8"—H8"B109.5
C15'—O6'—C6'115.0 (2)C7"—C8"—H8"C109.5
O5'—C1'—O1'110.7 (2)H8"A—C8"—H8"C109.5
O5'—C1'—C2'112.2 (2)H8"B—C8"—H8"C109.5
O1'—C1'—C2'104.6 (2)O8"—C9"—O2"123.8 (3)
O5'—C1'—H1'109.7O8"—C9"—C10"124.8 (3)
O1'—C1'—H1'109.7O2"—C9"—C10"111.4 (2)
C2'—C1'—H1'109.7C9"—C10"—H10G109.5
O2'—C2'—C3'110.3 (2)C9"—C10"—H10H109.5
O2'—C2'—C1'106.4 (2)H10G—C10"—H10H109.5
C3'—C2'—C1'109.8 (2)C9"—C10"—H10I109.5
O2'—C2'—H2'110.1H10G—C10"—H10I109.5
C3'—C2'—H2'110.1H10H—C10"—H10I109.5
C1'—C2'—H2'110.1O9"—C11"—O3"124.9 (3)
O3'—C3'—C2'108.9 (2)O9"—C11"—C12"126.1 (3)
O3'—C3'—C4'108.1 (2)O3"—C11"—C12"109.0 (3)
C2'—C3'—C4'112.4 (2)C11"—C12"—H12G109.5
O3'—C3'—H3'109.1C11"—C12"—H12H109.5
C2'—C3'—H3'109.1H12G—C12"—H12H109.5
C4'—C3'—H3'109.1C11"—C12"—H12I109.5
O4'—C4'—C3'108.81 (19)H12G—C12"—H12I109.5
O4'—C4'—C5'104.05 (18)H12H—C12"—H12I109.5
C3'—C4'—C5'111.7 (2)O10"—C13"—O4"122.8 (2)
O4'—C4'—H4'110.7O10"—C13"—C14"126.2 (2)
C3'—C4'—H4'110.7O4"—C13"—C14"111.0 (2)
C5'—C4'—H4'110.7C13"—C14"—H14G109.5
O5'—C5'—C6'107.4 (2)C13"—C14"—H14H109.5
O5'—C5'—C4'112.11 (19)H14G—C14"—H14H109.5
C6'—C5'—C4'109.20 (19)C13"—C14"—H14I109.5
O5'—C5'—H5'109.4H14G—C14"—H14I109.5
C6'—C5'—H5'109.4H14H—C14"—H14I109.5
C4'—C5'—H5'109.4O11"—C15"—O6"122.7 (3)
O6'—C6'—C5'108.5 (2)O11"—C15"—C16"126.3 (3)
O6'—C6'—H6'A110.0O6"—C15"—C16"111.0 (2)
C5'—C6'—H6'A110.0C15"—C16"—H16G109.5
O6'—C6'—H6'B110.0C15"—C16"—H16H109.5
C5'—C6'—H6'B110.0H16G—C16"—H16H109.5
H6'A—C6'—H6'B108.4C15"—C16"—H16I109.5
O7'—C7'—O1'123.3 (4)H16G—C16"—H16I109.5
O7'—C7'—C8'125.6 (4)H16H—C16"—H16I109.5
O1'—C7'—C8'111.1 (4)
C5—O5—C1—O160.8 (3)C2'—C3'—C4'—C5'47.5 (3)
C5—O5—C1—C256.2 (3)C1'—O5'—C5'—C6'175.1 (2)
C7—O1—C1—O579.9 (3)C1'—O5'—C5'—C4'55.2 (3)
C7—O1—C1—C2158.7 (2)O4'—C4'—C5'—O5'165.49 (19)
C9—O2—C2—C1127.8 (2)C3'—C4'—C5'—O5'48.3 (3)
C9—O2—C2—C3113.0 (2)O4'—C4'—C5'—C6'75.7 (2)
O5—C1—C2—O263.4 (3)C3'—C4'—C5'—C6'167.1 (2)
O1—C1—C2—O2176.36 (19)C15'—O6'—C6'—C5'165.1 (2)
O5—C1—C2—C354.0 (3)O5'—C5'—C6'—O6'70.8 (3)
O1—C1—C2—C366.2 (3)C4'—C5'—C6'—O6'167.5 (2)
C11—O3—C3—C4163.37 (19)C1'—O1'—C7'—O7'6.8 (5)
C11—O3—C3—C278.1 (3)C1'—O1'—C7'—C8'174.5 (3)
O2—C2—C3—O354.9 (3)C2'—O2'—C9'—O8'4.5 (4)
C1—C2—C3—O3171.7 (2)C2'—O2'—C9'—C10'175.4 (2)
O2—C2—C3—C462.8 (3)C3'—O3'—C11'—O9'A31.5 (8)
C1—C2—C3—C454.0 (3)C3'—O3'—C11'—O9'30.9 (7)
C13—O4—C4—C3115.8 (2)C3'—O3'—C11'—C12'177.7 (3)
C13—O4—C4—C5125.6 (2)C4'—O4'—C13'—O10'1.2 (4)
O3—C3—C4—O469.2 (2)C4'—O4'—C13'—C14'179.5 (2)
C2—C3—C4—O4171.9 (2)C6'—O6'—C15'—O11'3.8 (5)
O3—C3—C4—C5174.35 (19)C6'—O6'—C15'—C16'174.7 (3)
C2—C3—C4—C555.4 (3)C5"—O5"—C1"—O1"59.3 (2)
C1—O5—C5—C6175.7 (2)C5"—O5"—C1"—C2"59.0 (3)
C1—O5—C5—C457.1 (3)C7"—O1"—C1"—O5"79.7 (2)
O4—C4—C5—O5174.18 (18)C7"—O1"—C1"—C2"158.2 (2)
C3—C4—C5—O556.1 (3)C9"—O2"—C2"—C1"130.9 (2)
O4—C4—C5—C669.2 (2)C9"—O2"—C2"—C3"109.7 (2)
C3—C4—C5—C6172.7 (2)O5"—C1"—C2"—O2"67.9 (2)
C15—O6—C6—C5179.1 (2)O1"—C1"—C2"—O2"170.83 (18)
O5—C5—C6—O665.0 (2)O5"—C1"—C2"—C3"50.3 (3)
C4—C5—C6—O6175.72 (19)O1"—C1"—C2"—C3"71.0 (2)
C1—O1—C7—O710.2 (4)C11"—O3"—C3"—C4"110.3 (3)
C1—O1—C7—C8170.0 (2)C11"—O3"—C3"—C2"128.7 (3)
C2—O2—C9—O80.8 (4)O2"—C2"—C3"—O3"51.3 (3)
C2—O2—C9—C10179.2 (2)C1"—C2"—C3"—O3"167.32 (19)
C3—O3—C11—O97.6 (4)O2"—C2"—C3"—C4"67.5 (2)
C3—O3—C11—C12170.9 (2)C1"—C2"—C3"—C4"48.5 (3)
C4—O4—C13—O105.0 (3)C13"—O4"—C4"—C3"115.9 (2)
C4—O4—C13—C14175.5 (2)C13"—O4"—C4"—C5"126.0 (2)
C6—O6—C15—O115.4 (4)O3"—C3"—C4"—O4"70.9 (2)
C6—O6—C15—C16174.1 (2)C2"—C3"—C4"—O4"170.65 (18)
C5'—O5'—C1'—O1'56.8 (3)O3"—C3"—C4"—C5"171.52 (18)
C5'—O5'—C1'—C2'59.6 (3)C2"—C3"—C4"—C5"53.1 (2)
C7'—O1'—C1'—O5'113.1 (3)C1"—O5"—C5"—C6"175.25 (18)
C7'—O1'—C1'—C2'125.8 (3)C1"—O5"—C5"—C4"62.6 (2)
C9'—O2'—C2'—C3'108.0 (2)O4"—C4"—C5"—O5"174.17 (18)
C9'—O2'—C2'—C1'133.0 (2)C3"—C4"—C5"—O5"58.1 (2)
O5'—C1'—C2'—O2'63.2 (3)O4"—C4"—C5"—C6"67.6 (2)
O1'—C1'—C2'—O2'176.8 (2)C3"—C4"—C5"—C6"176.29 (19)
O5'—C1'—C2'—C3'56.2 (3)C15"—O6"—C6"—C5"178.52 (19)
O1'—C1'—C2'—C3'63.9 (3)O5"—C5"—C6"—O6"80.3 (2)
C11'—O3'—C3'—C2'112.0 (3)C4"—C5"—C6"—O6"160.38 (18)
C11'—O3'—C3'—C4'125.7 (3)C1"—O1"—C7"—O7"3.4 (4)
O2'—C2'—C3'—O3'53.4 (3)C1"—O1"—C7"—C8"176.5 (2)
C1'—C2'—C3'—O3'170.3 (2)C2"—O2"—C9"—O8"2.1 (4)
O2'—C2'—C3'—C4'66.4 (3)C2"—O2"—C9"—C10"177.8 (2)
C1'—C2'—C3'—C4'50.5 (3)C3"—O3"—C11"—O9"0.1 (5)
C13'—O4'—C4'—C3'96.8 (3)C3"—O3"—C11"—C12"178.5 (4)
C13'—O4'—C4'—C5'144.0 (2)C4"—O4"—C13"—O10"8.8 (4)
O3'—C3'—C4'—O4'77.9 (2)C4"—O4"—C13"—C14"172.1 (2)
C2'—C3'—C4'—O4'161.83 (19)C6"—O6"—C15"—O11"1.6 (4)
O3'—C3'—C4'—C5'167.7 (2)C6"—O6"—C15"—C16"178.6 (2)
2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl-(12)-\ 3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(13)-\ 1,2,4,6-tetra-O-acetyl-α-D-mannopyranose (III) top
Crystal data top
C40H54O27F(000) = 1020
Mr = 966.83Dx = 1.190 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 9.1043 (2) ÅCell parameters from 9335 reflections
b = 21.4770 (5) Åθ = 3.8–71.6°
c = 13.8106 (3) ŵ = 0.88 mm1
β = 91.8362 (8)°T = 120 K
V = 2699.04 (10) Å3Block, colorless
Z = 20.19 × 0.15 × 0.12 mm
Data collection top
Bruker APEXII CCD
diffractometer
9999 independent reflections
Radiation source: Incoatec micro-focus9956 reflections with I > 2σ(I)
MONTEL Multi-layer monochromatorRint = 0.022
Detector resolution: 8.33 pixels mm-1θmax = 71.7°, θmin = 3.2°
combination of ω and φ–scansh = 1111
Absorption correction: numerical
(SADABS; Krause et al., 2015)
k = 2426
Tmin = 0.864, Tmax = 0.950l = 1616
72001 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.061P)2 + 0.580P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.025
9999 reflectionsΔρmax = 0.53 e Å3
629 parametersΔρmin = 0.20 e Å3
1 restraintAbsolute structure: Flack x determined using 4517 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: dualAbsolute structure parameter: 0.069 (17)
Special details top

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. One acetate was disordered over two sites. This group was modeled with occupancies summed to unity yielding a 0.83:0.17 ratio. Minor component atoms were modeled with isotropic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O11.32946 (18)0.79339 (9)1.24283 (13)0.0372 (4)
O20.96145 (17)0.77217 (8)1.32418 (11)0.0288 (3)
O40.97619 (18)0.85795 (8)1.04730 (11)0.0297 (3)
O51.16089 (19)0.86883 (8)1.28676 (12)0.0335 (4)
O60.9541 (2)0.96229 (9)1.24464 (14)0.0455 (5)
O71.4749 (2)0.83303 (14)1.36352 (16)0.0594 (6)
O80.9267 (2)0.66907 (10)1.34400 (13)0.0423 (4)
O90.7595 (3)0.90429 (15)1.07179 (17)0.0676 (7)
O100.9104 (3)1.05340 (11)1.1710 (2)0.0629 (6)
C11.2023 (2)0.80665 (12)1.29819 (16)0.0304 (5)
H11.2258780.7983681.3682350.036*
C21.0832 (2)0.76164 (11)1.26250 (15)0.0260 (4)
H21.1181600.7175961.2678050.031*
C31.0383 (2)0.77745 (10)1.15805 (15)0.0231 (4)
H31.1228490.7686891.1156070.028*
C40.9978 (2)0.84550 (11)1.14916 (15)0.0266 (4)
H40.9056190.8542031.1842110.032*
C51.1236 (3)0.88684 (12)1.18868 (17)0.0319 (5)
H51.2113280.8805451.1480840.038*
C61.0861 (4)0.95461 (13)1.1895 (2)0.0432 (6)
H6A1.1680520.9787441.2197870.052*
H6B1.0689160.9698511.1224530.052*
C71.4610 (3)0.81115 (18)1.2824 (2)0.0480 (7)
C81.5798 (3)0.8039 (2)1.2107 (2)0.0555 (8)
H8A1.5669310.7643181.1761920.083*
H8B1.6758910.8043941.2447470.083*
H8C1.5743480.8383481.1640960.083*
C90.8956 (2)0.72171 (13)1.36255 (15)0.0329 (5)
C100.7813 (3)0.74238 (18)1.4313 (2)0.0484 (7)
H10A0.8258600.7706441.4795560.073*
H10B0.7410240.7059741.4640110.073*
H10C0.7021050.7640431.3952520.073*
C110.8490 (3)0.88528 (13)1.0181 (2)0.0393 (6)
C120.8394 (4)0.88916 (14)0.9092 (2)0.0465 (7)
H12A0.9335930.9036460.8851740.070*
H12B0.7616380.9184470.8893620.070*
H12C0.8168900.8479020.8823440.070*
C130.8733 (4)1.01297 (15)1.2252 (2)0.0507 (7)
C140.7319 (5)1.0111 (2)1.2775 (3)0.0684 (10)
H14A0.6602270.9856521.2407450.103*
H14B0.6936401.0534661.2841270.103*
H14C0.7492040.9928741.3419440.103*
O1'0.91482 (15)0.74073 (7)1.12571 (10)0.0231 (3)
O3'0.60166 (16)0.60693 (8)1.01198 (11)0.0291 (3)
O4'0.77799 (18)0.54379 (7)1.15035 (12)0.0294 (3)
O5'1.03456 (15)0.65715 (7)1.05320 (11)0.0244 (3)
O6'1.21573 (19)0.59833 (9)1.19189 (15)0.0409 (4)
O7'0.46227 (19)0.68752 (10)1.05404 (16)0.0470 (5)
O8'0.8241 (3)0.45956 (10)1.06250 (19)0.0619 (7)
O9'1.3643 (3)0.51718 (13)1.1744 (2)0.0691 (7)
C1'0.9394 (2)0.70827 (10)1.03845 (14)0.0225 (4)
H1'0.9837700.7375120.9912320.027*
C2'0.7874 (2)0.68834 (10)0.99914 (14)0.0217 (4)
H2'0.7188290.7246721.0003640.026*
C3'0.7268 (2)0.63544 (10)1.06026 (15)0.0229 (4)
H3'0.6964720.6525491.1239220.028*
C4'0.8386 (2)0.58428 (11)1.07812 (16)0.0257 (4)
H4'0.8574780.5609471.0171100.031*
C5'0.9804 (2)0.61240 (11)1.12112 (16)0.0265 (4)
H5'0.9592470.6338071.1834510.032*
C6'1.1005 (3)0.56551 (12)1.1382 (2)0.0354 (5)
H6'A1.0646240.5297541.1760100.042*
H6'B1.1368200.5499341.0758650.042*
C7'0.4762 (2)0.63990 (13)1.00940 (17)0.0329 (5)
C8'0.3613 (3)0.61019 (18)0.9454 (2)0.0481 (7)
H8'A0.3800270.6200600.8776570.072*
H8'B0.2643640.6260330.9620090.072*
H8'C0.3640670.5649550.9546080.072*
C9'0.7745 (3)0.48212 (12)1.1325 (2)0.0365 (5)
C10'0.7014 (3)0.44865 (13)1.2128 (2)0.0445 (6)
H10D0.7273630.4687941.2746820.067*
H10E0.7342450.4052061.2145910.067*
H10F0.5945560.4500271.2017440.067*
C11'1.3425 (3)0.56770 (15)1.2054 (2)0.0401 (6)
C12'1.4512 (3)0.60624 (18)1.2644 (2)0.0502 (7)
H12D1.4443180.6498621.2439530.075*
H12E1.5509430.5908411.2544200.075*
H12F1.4290810.6030401.3332130.075*
O1"0.79559 (16)0.66567 (7)0.90249 (10)0.0245 (3)
O2"0.65352 (16)0.72501 (8)0.67704 (11)0.0301 (3)
O3"0.7728 (2)0.61961 (10)0.59800 (13)0.0403 (4)
O4"1.06682 (19)0.64213 (9)0.62981 (12)0.0364 (4)
O5"0.90143 (15)0.74439 (7)0.81021 (11)0.0252 (3)
O6"1.19047 (17)0.77016 (9)0.85856 (12)0.0342 (4)
O7"0.44704 (19)0.66900 (10)0.64753 (14)0.0432 (4)
O8"0.6641 (4)0.53560 (15)0.6712 (3)0.0749 (12)0.827 (5)
O8"A0.8960 (18)0.5289 (8)0.6032 (12)0.067 (4)*0.173 (5)
O9"1.11849 (19)0.71860 (11)0.52457 (12)0.0426 (5)
O10"1.4233 (2)0.78024 (13)0.81525 (15)0.0535 (6)
C1"0.7713 (2)0.71123 (11)0.83031 (15)0.0252 (4)
H1"0.6961690.7413830.8530920.030*
C2"0.7082 (2)0.67716 (11)0.74130 (16)0.0289 (5)
H2"0.6264320.6489870.7599960.035*
C3"0.8267 (3)0.64023 (12)0.69179 (16)0.0309 (5)
H3"0.8560990.6034970.7324660.037*
C4"0.9596 (2)0.68095 (12)0.67517 (16)0.0293 (5)
H4"0.9315040.7163370.6313130.035*
C5"1.0168 (2)0.70609 (11)0.77303 (15)0.0262 (4)
H5"1.0392100.6708720.8185030.031*
C6"1.1499 (3)0.74652 (13)0.76334 (17)0.0343 (5)
H6"A1.2318060.7220030.7372390.041*
H6"B1.1276580.7814530.7184540.041*
C7"0.5163 (2)0.71590 (14)0.63722 (15)0.0334 (5)
C8"0.4666 (3)0.77199 (17)0.58164 (19)0.0459 (7)
H8"A0.4283420.8030210.6263440.069*
H8"B0.3890120.7601270.5343740.069*
H8"C0.5497490.7896850.5476780.069*
C9"0.6923 (5)0.56459 (19)0.5992 (3)0.0590 (12)0.827 (5)
C10"0.6462 (8)0.5496 (3)0.4958 (5)0.094 (2)0.827 (5)
H10G0.5754810.5808720.4718180.141*0.827 (5)
H10H0.6005200.5083320.4930710.141*0.827 (5)
H10I0.7326970.5500030.4553250.141*0.827 (5)
C9"A0.8129 (19)0.5637 (9)0.5572 (12)0.046 (4)*0.173 (5)
C10A0.751 (2)0.5543 (9)0.4603 (12)0.043 (4)*0.173 (5)
H10J0.6978930.5918050.4393120.064*0.173 (5)
H10K0.6837200.5188090.4603290.064*0.173 (5)
H10L0.8307010.5459720.4158480.064*0.173 (5)
C11"1.1276 (3)0.66525 (16)0.54952 (17)0.0389 (6)
C12"1.2047 (4)0.6143 (2)0.4952 (2)0.0578 (9)
H12G1.2595810.5877970.5414110.087*
H12H1.2728110.6330230.4500110.087*
H12I1.1318010.5891770.4591220.087*
C13"1.3317 (2)0.78755 (12)0.87336 (17)0.0309 (5)
C14"1.3529 (3)0.81831 (13)0.97007 (18)0.0354 (5)
H14D1.2836330.8529890.9750860.053*
H14E1.4537310.8340900.9769870.053*
H14F1.3353620.7879951.0214560.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0215 (8)0.0545 (12)0.0355 (9)0.0020 (7)0.0005 (6)0.0056 (8)
O20.0247 (7)0.0377 (9)0.0242 (7)0.0046 (6)0.0023 (6)0.0047 (6)
O40.0352 (8)0.0295 (8)0.0243 (7)0.0031 (6)0.0011 (6)0.0047 (6)
O50.0375 (9)0.0344 (9)0.0282 (8)0.0027 (7)0.0034 (6)0.0044 (6)
O60.0686 (13)0.0332 (10)0.0346 (9)0.0104 (9)0.0013 (8)0.0015 (7)
O70.0420 (11)0.0921 (19)0.0433 (11)0.0109 (11)0.0121 (9)0.0029 (11)
O80.0493 (11)0.0454 (12)0.0322 (9)0.0117 (9)0.0031 (8)0.0055 (8)
O90.0548 (13)0.099 (2)0.0487 (12)0.0307 (14)0.0019 (10)0.0128 (12)
O100.0669 (14)0.0381 (12)0.0818 (17)0.0008 (10)0.0240 (12)0.0112 (12)
C10.0242 (10)0.0406 (13)0.0262 (10)0.0017 (9)0.0013 (8)0.0023 (9)
C20.0227 (10)0.0304 (12)0.0249 (10)0.0018 (8)0.0014 (8)0.0002 (8)
C30.0173 (8)0.0271 (11)0.0248 (10)0.0013 (8)0.0005 (7)0.0013 (8)
C40.0287 (10)0.0289 (12)0.0221 (9)0.0023 (8)0.0004 (8)0.0019 (8)
C50.0373 (12)0.0318 (13)0.0266 (11)0.0067 (10)0.0002 (9)0.0024 (9)
C60.0641 (17)0.0309 (14)0.0345 (13)0.0069 (12)0.0010 (12)0.0008 (10)
C70.0286 (12)0.078 (2)0.0372 (14)0.0008 (13)0.0060 (10)0.0171 (13)
C80.0259 (12)0.097 (3)0.0431 (15)0.0058 (14)0.0042 (11)0.0111 (16)
C90.0281 (11)0.0481 (16)0.0222 (9)0.0015 (10)0.0026 (8)0.0061 (9)
C100.0343 (13)0.076 (2)0.0354 (13)0.0078 (13)0.0104 (10)0.0155 (13)
C110.0389 (13)0.0395 (14)0.0394 (13)0.0001 (11)0.0027 (10)0.0117 (11)
C120.0604 (17)0.0399 (15)0.0381 (14)0.0014 (13)0.0146 (12)0.0119 (11)
C130.0659 (19)0.0357 (15)0.0489 (16)0.0058 (14)0.0224 (14)0.0088 (12)
C140.072 (2)0.055 (2)0.077 (2)0.0185 (18)0.0012 (19)0.0107 (18)
O1'0.0190 (6)0.0274 (8)0.0228 (7)0.0023 (6)0.0017 (5)0.0001 (6)
O3'0.0196 (7)0.0344 (9)0.0332 (8)0.0050 (6)0.0014 (6)0.0022 (6)
O4'0.0308 (8)0.0260 (9)0.0314 (8)0.0018 (6)0.0018 (6)0.0030 (6)
O5'0.0172 (6)0.0269 (8)0.0292 (7)0.0011 (5)0.0017 (5)0.0004 (6)
O6'0.0251 (8)0.0450 (11)0.0520 (11)0.0065 (7)0.0089 (7)0.0010 (8)
O7'0.0261 (8)0.0524 (12)0.0621 (12)0.0081 (8)0.0041 (8)0.0075 (10)
O8'0.0851 (17)0.0298 (11)0.0729 (15)0.0036 (11)0.0384 (13)0.0094 (10)
O9'0.0382 (11)0.0646 (16)0.103 (2)0.0222 (11)0.0150 (12)0.0050 (15)
C1'0.0194 (9)0.0250 (11)0.0231 (9)0.0004 (8)0.0011 (7)0.0022 (8)
C2'0.0185 (9)0.0240 (10)0.0226 (9)0.0006 (7)0.0000 (7)0.0012 (8)
C3'0.0164 (8)0.0270 (10)0.0253 (9)0.0026 (8)0.0011 (7)0.0003 (8)
C4'0.0208 (9)0.0271 (11)0.0293 (10)0.0009 (8)0.0021 (8)0.0007 (8)
C5'0.0224 (10)0.0260 (11)0.0309 (10)0.0018 (8)0.0002 (8)0.0031 (8)
C6'0.0237 (10)0.0315 (13)0.0506 (14)0.0027 (9)0.0037 (9)0.0025 (10)
C7'0.0201 (10)0.0457 (15)0.0328 (11)0.0009 (9)0.0003 (8)0.0048 (10)
C8'0.0253 (12)0.075 (2)0.0436 (14)0.0093 (12)0.0057 (10)0.0007 (14)
C9'0.0339 (12)0.0261 (13)0.0497 (14)0.0010 (9)0.0037 (10)0.0027 (10)
C10'0.0458 (14)0.0316 (14)0.0563 (16)0.0016 (11)0.0045 (12)0.0132 (12)
C11'0.0256 (11)0.0552 (18)0.0396 (13)0.0072 (11)0.0002 (9)0.0143 (12)
C12'0.0298 (12)0.085 (2)0.0349 (13)0.0026 (13)0.0076 (10)0.0069 (14)
O1"0.0223 (7)0.0292 (8)0.0218 (7)0.0010 (6)0.0010 (5)0.0015 (6)
O2"0.0210 (7)0.0436 (10)0.0254 (7)0.0025 (6)0.0026 (6)0.0071 (6)
O3"0.0364 (9)0.0518 (12)0.0318 (9)0.0058 (8)0.0106 (7)0.0108 (8)
O4"0.0329 (8)0.0456 (11)0.0307 (8)0.0138 (7)0.0002 (6)0.0053 (7)
O5"0.0194 (7)0.0294 (8)0.0268 (7)0.0009 (6)0.0022 (5)0.0015 (6)
O6"0.0216 (7)0.0519 (11)0.0292 (8)0.0055 (7)0.0043 (6)0.0076 (7)
O7"0.0292 (8)0.0564 (12)0.0432 (10)0.0028 (8)0.0102 (7)0.0026 (9)
O8"0.077 (2)0.0451 (17)0.099 (3)0.0130 (14)0.0519 (19)0.0082 (16)
O9"0.0305 (9)0.0683 (14)0.0290 (8)0.0070 (8)0.0016 (6)0.0020 (9)
O10"0.0249 (8)0.0895 (17)0.0465 (11)0.0099 (9)0.0095 (8)0.0226 (11)
C1"0.0189 (9)0.0320 (11)0.0245 (9)0.0000 (8)0.0000 (7)0.0033 (8)
C2"0.0218 (9)0.0366 (13)0.0281 (10)0.0008 (8)0.0052 (8)0.0042 (9)
C3"0.0303 (11)0.0361 (13)0.0256 (10)0.0033 (9)0.0091 (8)0.0012 (9)
C4"0.0246 (10)0.0385 (13)0.0248 (10)0.0076 (9)0.0005 (8)0.0004 (9)
C5"0.0203 (9)0.0348 (13)0.0235 (9)0.0038 (8)0.0012 (7)0.0008 (8)
C6"0.0243 (10)0.0513 (15)0.0275 (10)0.0030 (10)0.0038 (8)0.0014 (10)
C7"0.0214 (10)0.0575 (16)0.0214 (9)0.0056 (10)0.0013 (8)0.0008 (10)
C8"0.0278 (12)0.075 (2)0.0347 (13)0.0109 (12)0.0026 (10)0.0181 (13)
C9"0.061 (2)0.043 (2)0.070 (3)0.0132 (17)0.041 (2)0.0164 (19)
C10"0.110 (5)0.076 (4)0.092 (4)0.025 (3)0.067 (4)0.044 (3)
C11"0.0257 (11)0.0667 (19)0.0239 (10)0.0133 (11)0.0040 (8)0.0069 (11)
C12"0.0461 (16)0.089 (3)0.0379 (14)0.0265 (16)0.0003 (12)0.0200 (15)
C13"0.0233 (10)0.0370 (13)0.0323 (11)0.0007 (9)0.0026 (8)0.0010 (9)
C14"0.0278 (11)0.0433 (15)0.0349 (12)0.0026 (10)0.0008 (9)0.0024 (10)
Geometric parameters (Å, º) top
O1—C71.355 (3)C5'—H5'1.0000
O1—C11.436 (3)C6'—H6'A0.9900
O2—C91.355 (3)C6'—H6'B0.9900
O2—C21.437 (3)C7'—C8'1.491 (4)
O4—C111.348 (3)C8'—H8'A0.9800
O4—C41.439 (3)C8'—H8'B0.9800
O5—C11.395 (3)C8'—H8'C0.9800
O5—C51.439 (3)C9'—C10'1.496 (4)
O6—C131.336 (4)C10'—H10D0.9800
O6—C61.452 (4)C10'—H10E0.9800
O7—C71.217 (4)C10'—H10F0.9800
O8—C91.195 (4)C11'—C12'1.510 (4)
O9—C111.191 (4)C12'—H12D0.9800
O10—C131.202 (4)C12'—H12E0.9800
C1—C21.523 (3)C12'—H12F0.9800
C1—H11.0000O1"—C1"1.409 (3)
C2—C31.525 (3)O2"—C7"1.363 (3)
C2—H21.0000O2"—C2"1.436 (3)
C3—O1'1.433 (2)O3"—C9"A1.380 (19)
C3—C41.511 (3)O3"—C9"1.391 (5)
C3—H31.0000O3"—C3"1.440 (3)
C4—C51.535 (3)O4"—C11"1.350 (3)
C4—H41.0000O4"—C4"1.442 (3)
C5—C61.495 (4)O5"—C1"1.418 (3)
C5—H51.0000O5"—C5"1.441 (2)
C6—H6A0.9900O6"—C13"1.348 (3)
C6—H6B0.9900O6"—C6"1.446 (3)
C7—C81.499 (4)O7"—C7"1.199 (4)
C8—H8A0.9800O8"—C9"1.208 (6)
C8—H8B0.9800O8"A—C9"A1.23 (2)
C8—H8C0.9800O9"—C11"1.199 (4)
C9—C101.498 (3)O10"—C13"1.186 (3)
C10—H10A0.9800C1"—C2"1.527 (3)
C10—H10B0.9800C1"—H1"1.0000
C10—H10C0.9800C2"—C3"1.519 (3)
C11—C121.506 (4)C2"—H2"1.0000
C12—H12A0.9800C3"—C4"1.516 (3)
C12—H12B0.9800C3"—H3"1.0000
C12—H12C0.9800C4"—C5"1.531 (3)
C13—C141.498 (6)C4"—H4"1.0000
C14—H14A0.9800C5"—C6"1.501 (3)
C14—H14B0.9800C5"—H5"1.0000
C14—H14C0.9800C6"—H6"A0.9900
O1'—C1'1.416 (2)C6"—H6"B0.9900
O3'—C7'1.343 (3)C7"—C8"1.491 (4)
O3'—C3'1.438 (2)C8"—H8"A0.9800
O4'—C9'1.347 (3)C8"—H8"B0.9800
O4'—C4'1.446 (3)C8"—H8"C0.9800
O5'—C1'1.409 (3)C9"—C10"1.510 (6)
O5'—C5'1.441 (3)C10"—H10G0.9800
O6'—C11'1.336 (3)C10"—H10H0.9800
O6'—C6'1.449 (3)C10"—H10I0.9800
O7'—C7'1.203 (3)C9"A—C10A1.45 (2)
O8'—C9'1.184 (3)C10A—H10J0.9800
O9'—C11'1.185 (4)C10A—H10K0.9800
C1'—C2'1.531 (3)C10A—H10L0.9800
C1'—H1'1.0000C11"—C12"1.511 (4)
C2'—O1"1.425 (2)C12"—H12G0.9800
C2'—C3'1.529 (3)C12"—H12H0.9800
C2'—H2'1.0000C12"—H12I0.9800
C3'—C4'1.512 (3)C13"—C14"1.497 (3)
C3'—H3'1.0000C14"—H14D0.9800
C4'—C5'1.528 (3)C14"—H14E0.9800
C4'—H4'1.0000C14"—H14F0.9800
C5'—C6'1.500 (3)
C7—O1—C1116.5 (2)H6'A—C6'—H6'B108.8
C9—O2—C2117.74 (18)O7'—C7'—O3'122.6 (2)
C11—O4—C4117.53 (19)O7'—C7'—C8'125.7 (2)
C1—O5—C5114.75 (18)O3'—C7'—C8'111.7 (2)
C13—O6—C6116.5 (3)C7'—C8'—H8'A109.5
O5—C1—O1110.4 (2)C7'—C8'—H8'B109.5
O5—C1—C2112.55 (18)H8'A—C8'—H8'B109.5
O1—C1—C2106.23 (18)C7'—C8'—H8'C109.5
O5—C1—H1109.2H8'A—C8'—H8'C109.5
O1—C1—H1109.2H8'B—C8'—H8'C109.5
C2—C1—H1109.2O8'—C9'—O4'123.0 (2)
O2—C2—C1105.25 (17)O8'—C9'—C10'126.8 (3)
O2—C2—C3109.71 (16)O4'—C9'—C10'110.2 (2)
C1—C2—C3109.35 (18)C9'—C10'—H10D109.5
O2—C2—H2110.8C9'—C10'—H10E109.5
C1—C2—H2110.8H10D—C10'—H10E109.5
C3—C2—H2110.8C9'—C10'—H10F109.5
O1'—C3—C4108.66 (16)H10D—C10'—H10F109.5
O1'—C3—C2110.86 (16)H10E—C10'—H10F109.5
C4—C3—C2110.45 (18)O9'—C11'—O6'123.7 (3)
O1'—C3—H3108.9O9'—C11'—C12'125.6 (3)
C4—C3—H3108.9O6'—C11'—C12'110.7 (3)
C2—C3—H3108.9C11'—C12'—H12D109.5
O4—C4—C3106.53 (18)C11'—C12'—H12E109.5
O4—C4—C5108.50 (17)H12D—C12'—H12E109.5
C3—C4—C5110.68 (18)C11'—C12'—H12F109.5
O4—C4—H4110.3H12D—C12'—H12F109.5
C3—C4—H4110.3H12E—C12'—H12F109.5
C5—C4—H4110.3C1"—O1"—C2'114.44 (16)
O5—C5—C6107.6 (2)C7"—O2"—C2"116.23 (19)
O5—C5—C4109.28 (18)C9"A—O3"—C3"123.2 (7)
C6—C5—C4113.5 (2)C9"—O3"—C3"114.6 (3)
O5—C5—H5108.8C11"—O4"—C4"116.4 (2)
C6—C5—H5108.8C1"—O5"—C5"113.96 (17)
C4—C5—H5108.8C13"—O6"—C6"116.71 (17)
O6—C6—C5107.9 (2)O1"—C1"—O5"111.97 (16)
O6—C6—H6A110.1O1"—C1"—C2"106.46 (18)
C5—C6—H6A110.1O5"—C1"—C2"112.22 (17)
O6—C6—H6B110.1O1"—C1"—H1"108.7
C5—C6—H6B110.1O5"—C1"—H1"108.7
H6A—C6—H6B108.4C2"—C1"—H1"108.7
O7—C7—O1123.0 (3)O2"—C2"—C3"109.43 (18)
O7—C7—C8126.3 (3)O2"—C2"—C1"105.58 (18)
O1—C7—C8110.6 (2)C3"—C2"—C1"111.01 (17)
C7—C8—H8A109.5O2"—C2"—H2"110.2
C7—C8—H8B109.5C3"—C2"—H2"110.2
H8A—C8—H8B109.5C1"—C2"—H2"110.2
C7—C8—H8C109.5O3"—C3"—C4"106.99 (19)
H8A—C8—H8C109.5O3"—C3"—C2"109.80 (18)
H8B—C8—H8C109.5C4"—C3"—C2"110.4 (2)
O8—C9—O2124.2 (2)O3"—C3"—H3"109.9
O8—C9—C10126.2 (3)C4"—C3"—H3"109.9
O2—C9—C10109.6 (2)C2"—C3"—H3"109.9
C9—C10—H10A109.5O4"—C4"—C3"106.7 (2)
C9—C10—H10B109.5O4"—C4"—C5"111.83 (17)
H10A—C10—H10B109.5C3"—C4"—C5"108.67 (18)
C9—C10—H10C109.5O4"—C4"—H4"109.9
H10A—C10—H10C109.5C3"—C4"—H4"109.9
H10B—C10—H10C109.5C5"—C4"—H4"109.9
O9—C11—O4124.2 (3)O5"—C5"—C6"107.54 (19)
O9—C11—C12125.7 (3)O5"—C5"—C4"106.55 (16)
O4—C11—C12110.1 (2)C6"—C5"—C4"112.21 (18)
C11—C12—H12A109.5O5"—C5"—H5"110.1
C11—C12—H12B109.5C6"—C5"—H5"110.1
H12A—C12—H12B109.5C4"—C5"—H5"110.1
C11—C12—H12C109.5O6"—C6"—C5"107.78 (17)
H12A—C12—H12C109.5O6"—C6"—H6"A110.2
H12B—C12—H12C109.5C5"—C6"—H6"A110.2
O10—C13—O6123.4 (3)O6"—C6"—H6"B110.2
O10—C13—C14125.7 (3)C5"—C6"—H6"B110.2
O6—C13—C14110.9 (3)H6"A—C6"—H6"B108.5
C13—C14—H14A109.5O7"—C7"—O2"123.5 (2)
C13—C14—H14B109.5O7"—C7"—C8"126.0 (2)
H14A—C14—H14B109.5O2"—C7"—C8"110.5 (2)
C13—C14—H14C109.5C7"—C8"—H8"A109.5
H14A—C14—H14C109.5C7"—C8"—H8"B109.5
H14B—C14—H14C109.5H8"A—C8"—H8"B109.5
C1'—O1'—C3113.11 (15)C7"—C8"—H8"C109.5
C7'—O3'—C3'116.62 (18)H8"A—C8"—H8"C109.5
C9'—O4'—C4'118.19 (19)H8"B—C8"—H8"C109.5
C1'—O5'—C5'113.07 (15)O8"—C9"—O3"125.0 (3)
C11'—O6'—C6'116.1 (2)O8"—C9"—C10"127.5 (5)
O5'—C1'—O1'111.93 (16)O3"—C9"—C10"107.5 (5)
O5'—C1'—C2'112.21 (17)C9"—C10"—H10G109.5
O1'—C1'—C2'105.90 (16)C9"—C10"—H10H109.5
O5'—C1'—H1'108.9H10G—C10"—H10H109.5
O1'—C1'—H1'108.9C9"—C10"—H10I109.5
C2'—C1'—H1'108.9H10G—C10"—H10I109.5
O1"—C2'—C3'107.08 (17)H10H—C10"—H10I109.5
O1"—C2'—C1'110.75 (16)O8"A—C9"A—O3"119.1 (15)
C3'—C2'—C1'110.49 (16)O8"A—C9"A—C10A127.4 (18)
O1"—C2'—H2'109.5O3"—C9"A—C10A113.5 (14)
C3'—C2'—H2'109.5C9"A—C10A—H10J109.5
C1'—C2'—H2'109.5C9"A—C10A—H10K109.5
O3'—C3'—C4'106.58 (17)H10J—C10A—H10K109.5
O3'—C3'—C2'110.79 (16)C9"A—C10A—H10L109.5
C4'—C3'—C2'112.14 (16)H10J—C10A—H10L109.5
O3'—C3'—H3'109.1H10K—C10A—H10L109.5
C4'—C3'—H3'109.1O9"—C11"—O4"124.2 (2)
C2'—C3'—H3'109.1O9"—C11"—C12"125.3 (3)
O4'—C4'—C3'106.25 (16)O4"—C11"—C12"110.5 (3)
O4'—C4'—C5'107.81 (17)C11"—C12"—H12G109.5
C3'—C4'—C5'109.39 (18)C11"—C12"—H12H109.5
O4'—C4'—H4'111.1H12G—C12"—H12H109.5
C3'—C4'—H4'111.1C11"—C12"—H12I109.5
C5'—C4'—H4'111.1H12G—C12"—H12I109.5
O5'—C5'—C6'106.68 (18)H12H—C12"—H12I109.5
O5'—C5'—C4'108.25 (17)O10"—C13"—O6"123.3 (2)
C6'—C5'—C4'113.47 (19)O10"—C13"—C14"126.0 (2)
O5'—C5'—H5'109.4O6"—C13"—C14"110.66 (19)
C6'—C5'—H5'109.4C13"—C14"—H14D109.5
C4'—C5'—H5'109.4C13"—C14"—H14E109.5
O6'—C6'—C5'105.4 (2)H14D—C14"—H14E109.5
O6'—C6'—H6'A110.7C13"—C14"—H14F109.5
C5'—C6'—H6'A110.7H14D—C14"—H14F109.5
O6'—C6'—H6'B110.7H14E—C14"—H14F109.5
C5'—C6'—H6'B110.7
C5—O5—C1—O160.1 (2)C1'—O5'—C5'—C4'64.3 (2)
C5—O5—C1—C258.4 (2)O4'—C4'—C5'—O5'174.82 (17)
C7—O1—C1—O579.9 (3)C3'—C4'—C5'—O5'59.7 (2)
C7—O1—C1—C2157.8 (2)O4'—C4'—C5'—C6'67.0 (2)
C9—O2—C2—C1132.62 (19)C3'—C4'—C5'—C6'177.91 (19)
C9—O2—C2—C3109.8 (2)C11'—O6'—C6'—C5'172.2 (2)
O5—C1—C2—O263.7 (2)O5'—C5'—C6'—O6'69.4 (2)
O1—C1—C2—O2175.35 (17)C4'—C5'—C6'—O6'171.50 (19)
O5—C1—C2—C354.1 (2)C3'—O3'—C7'—O7'8.3 (3)
O1—C1—C2—C366.9 (2)C3'—O3'—C7'—C8'171.5 (2)
O2—C2—C3—O1'58.4 (2)C4'—O4'—C9'—O8'3.1 (4)
C1—C2—C3—O1'173.35 (17)C4'—O4'—C9'—C10'177.1 (2)
O2—C2—C3—C462.1 (2)C6'—O6'—C11'—O9'1.6 (4)
C1—C2—C3—C452.8 (2)C6'—O6'—C11'—C12'178.5 (2)
C11—O4—C4—C3127.6 (2)C3'—C2'—O1"—C1"147.46 (16)
C11—O4—C4—C5113.2 (2)C1'—C2'—O1"—C1"92.0 (2)
O1'—C3—C4—O465.6 (2)C2'—O1"—C1"—O5"85.0 (2)
C2—C3—C4—O4172.57 (16)C2'—O1"—C1"—C2"152.05 (16)
O1'—C3—C4—C5176.61 (16)C5"—O5"—C1"—O1"62.2 (2)
C2—C3—C4—C554.8 (2)C5"—O5"—C1"—C2"57.5 (2)
C1—O5—C5—C6178.5 (2)C7"—O2"—C2"—C3"107.3 (2)
C1—O5—C5—C457.9 (3)C7"—O2"—C2"—C1"133.17 (19)
O4—C4—C5—O5171.84 (18)O1"—C1"—C2"—O2"167.27 (16)
C3—C4—C5—O555.3 (2)O5"—C1"—C2"—O2"69.9 (2)
O4—C4—C5—C668.1 (2)O1"—C1"—C2"—C3"74.2 (2)
C3—C4—C5—C6175.3 (2)O5"—C1"—C2"—C3"48.6 (2)
C13—O6—C6—C5156.1 (2)C9"A—O3"—C3"—C4"94.1 (9)
O5—C5—C6—O665.2 (3)C9"—O3"—C3"—C4"155.8 (2)
C4—C5—C6—O655.8 (3)C9"A—O3"—C3"—C2"146.1 (9)
C1—O1—C7—O75.3 (4)C9"—O3"—C3"—C2"84.3 (3)
C1—O1—C7—C8170.9 (3)O2"—C2"—C3"—O3"51.7 (3)
C2—O2—C9—O84.5 (3)C1"—C2"—C3"—O3"167.86 (19)
C2—O2—C9—C10174.87 (19)O2"—C2"—C3"—C4"66.0 (2)
C4—O4—C11—O96.5 (4)C1"—C2"—C3"—C4"50.1 (2)
C4—O4—C11—C12174.7 (2)C11"—O4"—C4"—C3"130.7 (2)
C6—O6—C13—O105.7 (4)C11"—O4"—C4"—C5"110.7 (2)
C6—O6—C13—C14172.9 (3)O3"—C3"—C4"—O4"61.6 (2)
C4—C3—O1'—C1'111.97 (18)C2"—C3"—C4"—O4"178.99 (16)
C2—C3—O1'—C1'126.47 (18)O3"—C3"—C4"—C5"177.71 (18)
C5'—O5'—C1'—O1'59.1 (2)C2"—C3"—C4"—C5"58.3 (2)
C5'—O5'—C1'—C2'59.8 (2)C1"—O5"—C5"—C6"175.40 (16)
C3—O1'—C1'—O5'74.0 (2)C1"—O5"—C5"—C4"64.1 (2)
C3—O1'—C1'—C2'163.46 (16)O4"—C4"—C5"—O5"179.36 (18)
O5'—C1'—C2'—O1"68.7 (2)C3"—C4"—C5"—O5"63.2 (2)
O1'—C1'—C2'—O1"168.93 (16)O4"—C4"—C5"—C6"61.9 (3)
O5'—C1'—C2'—C3'49.8 (2)C3"—C4"—C5"—C6"179.4 (2)
O1'—C1'—C2'—C3'72.6 (2)C13"—O6"—C6"—C5"156.3 (2)
C7'—O3'—C3'—C4'164.71 (18)O5"—C5"—C6"—O6"60.4 (2)
C7'—O3'—C3'—C2'73.0 (2)C4"—C5"—C6"—O6"177.25 (19)
O1"—C2'—C3'—O3'46.1 (2)C2"—O2"—C7"—O7"5.8 (3)
C1'—C2'—C3'—O3'166.79 (16)C2"—O2"—C7"—C8"173.5 (2)
O1"—C2'—C3'—C4'72.8 (2)C3"—O3"—C9"—O8"1.7 (5)
C1'—C2'—C3'—C4'47.8 (2)C3"—O3"—C9"—C10"179.4 (3)
C9'—O4'—C4'—C3'129.7 (2)C3"—O3"—C9"A—O8"A2 (2)
C9'—O4'—C4'—C5'113.1 (2)C3"—O3"—C9"A—C10A176.8 (10)
O3'—C3'—C4'—O4'69.0 (2)C4"—O4"—C11"—O9"13.9 (3)
C2'—C3'—C4'—O4'169.62 (16)C4"—O4"—C11"—C12"164.8 (2)
O3'—C3'—C4'—C5'174.90 (16)C6"—O6"—C13"—O10"5.4 (4)
C2'—C3'—C4'—C5'53.5 (2)C6"—O6"—C13"—C14"172.8 (2)
C1'—O5'—C5'—C6'173.25 (18)
Average molecular parametersa in (I), (II), and (III) top
Molecular ParameterαMan(OAc)5, (I)MeαMan(OAc)4, (II)Man3(OAc)11, (III)
Bond lengths (Å)
rCC (endocyclic)1.524 ± 0.0061.525 ± 0.0051.523 ± 0.009
rC5,C61.508 ± 0.0051.511 (2)1.500 ± 0.003
rC,Ob1.443 ± 0.0041.441 ± 0.0021.442 ± 0.006
rO,Ccar1.356 ± 0.0081.353 ± 0.0091.348 ± 0.008
rCcar,Ocar1.195 ± 0.0071.198 ± 0.0061.197 ± 0.01
rCcar,CMe1.496 ± 0.0051.494 ± 0.0011.500 ± 0.008
Bond angles (°)
C5—O5—C1114.2 ± 0.5113.61 (12)113.9 ± 0.8
C—O—Ccar116.7 ± 1.6116.7 ± 0.7116.9 ± 0.8
O—Ccar—Ocar123.3 ± 0.7123.4 ± 0.4123.6 ± 0.7
O—Ccar—CMe111.0 ± 1.1111.1 ± 0.3110.6 ± 0.7
Ocar—Ccar—CMe125.9 ± 0.7125.5 ± 0.5125.9 ± 0.5
Torsion angles (°)
C—O—Ccar—CMe180.1 ± 5.4 (trans)178.4 ± 7.4 (trans)180.0 ± 8.1 (trans)
-65.5 (3) (gg) (R1)
O5—C5—C6—O672.0 ± 7.7 (gt)65.16 (16) (gt)69.5 (2) (gt) (R2)
60.5 (2) (gt) (R3)
Notes: (a) values ± standard deviations; `car' denotes carbonyl C atoms and `Me' denotes methyl C atoms, in an O-acetyl side chain. (b) Only C—O bonds involved in O-acetylation. gg = gauche–gauche and gt = gauche–trans.
Exocyclic C—O bond conformations in (I), (II), and (III) top
Cx/Ox—Cy—Oy—Ccar torsion angleaTorsion angle (°)Deviation from idealized rotamerb (°)
(Ia)
O5—C1—O1—C1car79.9 (3)-40.1
C1—C2—O2—C2car-127.8 (2)-7.8
C2—C3—O3—C3car-78.1 (3)+41.9
C3—C4—O4—C4car115.8 (2)-4.2
C5—C6—O6—C6car179.1 (2)-0.9
(Ib)
O5—C1—O1—C1car113.1 (3)-6.9
C1—C2—O2—C2car-133.0 (2)-13.0
C3—C4—O4—C4car96.8 (2)-23.2
C5—C6—O6—C6car165.2 (2)-14.8
(Ic)
O5—C1—O1—C1car79.7 (2)-40.3
C1—C2—O2—C2car-131.0 (2)-11.0
C2—C3—O3—C3car-128.7 (3)-8.7
C3—C4—O4—C4car115.9 (2)-4.1
C5—C6—O6—C6car-178.52 (19) (181.48)+1.5
(II)
C1—C2—O2—C2car-136.57 (14)-16.6
C2—C3—O3—C3car-78.87 (17)+41.1
C3—C4—O4—C4car124.93 (15)+4.9
C5—C6—O6—C6car138.41 (15)-41.6
(III) (R1)
O5—C1—O1—C1car79.9 (3)-40.1
C1—C2—O2—C2car-132.62 (19)-12.6
C3—C4—O4—C4car127.6 (2)+7.6
C5—C6—O6—C6car-156.1 (2) (203.9)+23.9
(III) (R2)
C2—C3—O3—C3car-73.0 (2)+47.0
C3—C4—O4—C4car129.7 (2)+9.7
C5–C6—O6—C6car-172.2 (2) (187.8)+7.8
(III) (R3)
C1—C2—O2—C2car-133.17 (19)-13.2
C3—C4—O4—C4car130.7 (2)+10.7
C5—C6—O6—C6car156.3 (2) (203.7)+23.7
Notes: (a) subscript `car' denotes the carbonyl C atom in an O-acetyl side chain. (b) Idealized C—O torsion angles are as follows: O5—C1—O1—C1car = 120°, C1—C2—O2—C2car = -120°, C2—C3—O3—C3car = -120°, C3—C4—O4—C4car = 120°, and C5—C6—O6—C6car = 180°. Values were calculated as [observed value - idealized value]. Some values (noted in parentheses) were calculated against the positive rotation value.
Cremer–Pople puckering parameters in compounds (I)–(V) top
Compoundθ (°)φ (°)Q (Å)q2 (Å)q3 (Å)
(Ia)4.2 (3)215 (4)0.555 (3)0.038 (3)0.554 (3)
(Ib)5.6 (3)62 (3)0.523 (3)0.047 (3)0.521 (3)
(Ic)6.5 (3)298 (2)0.553 (3)0.067 (3)0.550 (3)
(II)4.82 (18)282 (2)0.5757 (17)0.0485 (18)0.5737 (17)
(III) (R1)a0.6 (2)236 (7)0.553 (2)0.019 (2)0.553 (2)
(III) (R2)8.1 (2)302.3 (15)0.562 (2)0.082 (2)0.557 (2)
(III) (R3)10.2 (2)276.0 (2)0.581 (2)0.104 (2)0.572 (2)
(IV)b1.22860.5570.01180.5569
(V) (R1)10.7 (3)100.1 (18)0.521 (3)0.097 (3)0.512 (3)
(V) (R2)3.9 (3)199 (5)0.535 (3)0.036 (3)0.534 (3)
Average5.6 ± 3.4226 ± 84
Notes: (a) for definitions of residues R1–R3 in (III) and R1–R2 in (V), see structures (III) and (V) in the text. (b) Errors were not reported for structure (IV).
Selected bond lengths, bond angles and torsion angles in αMan(OAc)5 (Ia), (Ib), and (Ic) top
Structural parametera(Ia)(Ib)(Ic)
Bond lengths (Å)
C1—C21.522 (4)1.519 (4)1.523 (3)
C2—C31.530 (3)1.516 (4)1.523 (3)
C3—C41.522 (3)1.519 (3)1.520 (3)
C4—C51.535 (4)1.533 (3)1.530 (3)
C5—C61.508 (3)1.503 (3)1.512 (3)
C1—O11.435 (4)1.448 (3)1.433 (3)
C1—O51.395 (3)1.399 (3)1.404 (3)
C2—O21.435 (3)1.440 (3)1.449 (3)
C3—O31.437 (3)1.443 (3)1.443 (3)
C4—O41.446 (3)1.442 (3)1.442 (3)
C5—O51.439 (3)1.439 (3)1.440 (3)
C6—O61.444 (3)1.446 (3)1.445 (3)
O1—C1car1.370 (4)1.350 (4)1.364 (3)
O2—C2car1.358 (3)1.363 (3)1.356 (3)
O3—C3car1.363 (3)disordered1.354 (4)
O4—C4car1.357 (3)1.360 (3)1.350 (3)
O6—C6car1.342 (3)1.344 (3)1.352 (3)
C1car—O1car1.198 (4)1.177 (5)1.188 (4)
C2car—O2car1.194 (4)1.199 (4)1.198 (4)
C3car—O3car1.206 (4)disordered1.193 (4)
C4car—O4car1.202 (3)1.192 (4)1.195 (4)
C6car—O6car1.205 (4)1.190 (4)1.196 (4)
O1car—C1Me1.489 (5)1.494 (6)1.502 (4)
O2car—C2Me1.495 (4)1.494 (4)1.498 (4)
O3car—C3Me1.491 (4)1.491 (4)1.499 (5)
O4car—C4Me1.494 (3)1.498 (4)1.499 (3)
O6car—C6Me1.505 (4)1.489 (4)1.499 (4)
Bond angles (°)
C5—O5—C1114.78 (19)114.0 (2)113.96 (18)
C1—O1—C1car117.0 (2)118.6 (3)114.66 (19)
C2—O2—C2car117.3 (2)115.9 (2)116.9 (2)
C3—O3—C3car115.1 (2)118.9 (2)118.1 (2)
C4—O4—C4car116.72 (19)118.64 (19)117.81 (19)
C6—O6—C6car113.7 (2)115.0 (2)115.94 (19)
O1—C1car—O1car122.6 (3)123.3 (4)123.0 (3)
O2—C2car—O2car123.3 (3)123.6 (3)123.8 (3)
O3—C3car—O3car122.4 (3)disordered124.9 (3)
O4—C4car—O4car123.2 (2)123.8 (3)122.8 (2)
O6—C6car—O6car123.8 (3)122.9 (3)122.7 (2)
O1—C1car—C1Me110.4 (3)111.1 (4)110.5 (2)
O2—C2car—C2Me110.7 (2)110.8 (2)111.4 (2)
O3—C3car—C3Me111.2 (3)113.7 (3)109.0 (3)
O4—C4car—C4Me111.2 (2)109.6 (2)111.0 (2)
O6—C6car—C6Me111.0 (3)112.5 (2)110.9 (2)
O1car—C1car—C1Me126.9 (3)125.6 (4)126.5 (2)
O2car—C2car—C2Me126.1 (2)125.6 (3)124.8 (3)
O3car—C3car—C3Me126.4 (3)disordered126.1 (3)
O4car—C4car—C4Me125.6 (2)126.6 (3)126.2 (2)
O6car—C6car—C6Me125.2 (3)124.6 (3)126.3 (3)
Torsion angles (°)
C1—C2—C3—C4-54.0 (3)-50.5 (3)-48.5 (3)
C1—O5—C5—C457.1 (3)55.2 (3)62.5 (2)
O5—C1—O1—C1car79.9 (3)113.1 (3)79.7 (2)
C1—C2—O2—C2car-127.8 (2)-133.0 (2)-131.0 (2)
C2—C3—O3—C3car-78.1 (3)-112.0 (3)-128.7 (3)
C3—C4—O4—C4car115.8 (2)96.8 (2)115.9 (2)
C5—C6—O6—C6car179.1 (2)165.2 (2)-178.52 (19)
C1—O1—C1car—C1Me-170.0 (2)174.6 (3)-176.5 (2)
C2—O2—C2car—C2Me179.1 (2)175.4 (2)177.8 (2)
C3—O3—C3car—C3Me170.9 (2)-177.7 (3)-178.4 (4)
C4—O4—C4car—C4Me175.5 (2)-179.5 (2)-172.1 (2)
C6—O6—C6car—C6Me-174.2 (2)174.8 (3)-178.6 (2)
O5—C5—C6—O665.0 (2) (gt)70.8 (3) (gt)80.3 (2) (gt)
Notes: (a) subscripts `car' denote carbonyl C atoms and subscripts `Me' denote methyl C atoms in an O-acetyl side chain. gg = gauche–trans.
Selected bond lengths, bond angles and torsion angles in MeαMan(OAc4), (II) top
Structural parameteraRedetermined structureReported structureb
Bond lengths (Å)
C1—C21.524 (2)1.522
C2—C31.528 (2)1.531
C3—C41.517 (2)1.513
C4—C51.529 (2)1.531
C5—C61.511 (2)1.508
C1—O11.400 (2)1.402
C1—O51.418 (2)1.417
C2—O21.440 (2)1.441
C3—O31.4394 (19)1.439
C4—O41.4418 (19)1.444
C5—O51.4362 (19)1.438
C6—O61.443 (2)1.445
O1—CH31.431 (2)1.433
O2—C2car1.360 (2)1.360
O3—C3car1.355 (2)1.351
O4—C4car1.357 (2)1.360
O6—C6car1.339 (2)1.341
C2car—O2car1.201 (2)1.201
C3car—O3car1.205 (2)1.204
C4car—O4car1.191 (3)1.191
C6car—O6car1.195 (2)1.197
C2car—C2Me1.494 (2)1.498
C3car—C3Me1.494 (2)1.499
C4car—C4Me1.492 (3)1.490
C6car—C6Me1.494 (2)1.493
Bond angles (°)
C5—O5—C1113.61 (12)113.53
C1—O1—CH3112.64 (13)112.59
C2—O2—C2car116.10 (13)116.03
C3—O3—C3car116.21 (13)116.40
C4—O4—C4car116.91 (13)116.71
C6—O6—C6car117.69 (14)117.49
O2—C2car—O2car123.34 (16)123.32
O3—C3car—O3car123.48 (16)123.54
O4—C4car—O4car122.91 (17)123.09
O6—C6car—O6car123.75 (17)123.92
O2—C2car—C2Me111.38 (14)111.29
O3—C3car—C3Me110.58 (15)110.75
O4—C4car—C4Me111.14 (15)110.85
O6—C6car—C6Me111.23 (15)111.12
O2car—C2car—C2Me125.28 (16)125.38
O3car—C3car—C3Me125.93 (16)125.70
O4car—C4car—C4Me125.94 (18)126.05
O6car—C6car—C6Me125.01 (17)124.96
Torsion angles (°)
C1—C2—C3—C4-52.21 (17)-52.06
C1—O5—C5—C462.50 (17)62.02
O5—C1—O1—CH363.15 (18)63.08
C1—C2—O2—C2car-136.57 (14)-136.66
C2—C3—O3—C3car-78.87 (17)-78.58
C3—C4—O4—C4car124.93 (15)125.25
C5—C6—O6—C6car138.41 (15)137.57
C2—O2—C2car—C2Me169.26 (14)168.68
C3—O3—C3car—C3Me-179.18 (15)-179.12
C4—O4—C4car—C4Me-173.07 (14)-173.23
C6—O6—C6car—C6Me176.78 (14)177.16
O5—C5—C6—O665.16 (16) (gt)64.94 (gt)
Notes: (a) subscripts `car' denote carbonyl C atoms and subscripts `Me' denote methyl C atoms in an O-acetyl side chain. (b) Data taken from Szeleszczuk et al. (2017). gt = gauche–trans.
Selected bond lengths, bond angles and torsion angles in Man3(OAc)11, (III) top
Structural parameteraR1bR2R3
Bond lengths (Å)
C1—C21.521 (3)1.527 (3)1.528 (3)
C2—C31.522 (3)1.532 (3)1.520 (3)
C3—C41.507 (3)1.514 (3)1.511 (3)
C4—C51.533 (3)1.528 (3)1.532 (3)
C5—C61.500 (4)1.497 (3)1.503 (3)
C1—O11.437 (3)1.417 (2)1.411 (3)
C1—O51.394 (3)1.410 (3)1.417 (3)
C2—O21.438 (3)1.429 (2)1.441 (3)
C3—O31.436 (2)1.436 (2)1.438 (3)
C4—O41.438 (3)1.447 (3)1.439 (3)
C5—O51.439 (3)1.439 (3)1.442 (3)
C6—O61.457 (4)1.448 (3)1.441 (3)
O1—C1car1.354 (3)
O2—C2car1.355 (3)1.363 (3)
O3—C3car1.341 (3)disordered
O4—C4car1.347 (3)1.347 (3)1.349 (3)
O6—C6car1.337 (4)1.337 (3)1.346 (3)
C1car—O1car1.215 (4)
C2car—O2car1.190 (4)1.191 (4)
C3car—O3car1.206 (3)disordered
C4car—O4car1.194 (4)1.186 (4)1.201 (4)
C6car—O6car1.210 (4)1.188 (4)1.189 (3)
O1car—C1Me1.499 (4)
O2car—C2Me1.502(41.495 (4)
O3car—C3Me1.493 (4)1.509 (6)
O4car—C4Me1.506 (4)1.494 (4)1.513 (4)
O6car—C6Me1.487 (6)1.508 (4)1.496 (3)
Bond angles (°)
C5—O5—C1114.59 (18)113.06 (15)113.99 (17)
C1—O1—C1car116.6 (2)
C2—O2—C2car117.88 (19)115.86 (19)
C3—O3—C3car116.73 (19)disordered
C4—O4—C4car117.72 (19)118.31 (19)116.7 (2)
C6—O6—C6car116.7 (3)116.1 (2)116.72 (17)
O1—C1car—O1car123.1 (3)
O2—C2car—O2car124.2 (2)124.0 (2)
O3—C3car—O3car122.6 (2)124.9 (3)
O4—C4car—O4car124.2 (3)122.8 (3)124.0 (2)
O6—C6car—O6car122.8 (3)123.6 (3)123.3 (2)
O1—C1car—C1Me110.5 (3)
O2—C2car—C2Me109.5 (2)110.1 (2)
O3—C3car—C3Me111.9 (2)disordered
O4—C4car—C4Me110.2 (2)110.3 (2)110.8 (3)
O6—C6car—C6Me111.3 (3)110.6 (3)110.72 (19)
O1car—C1car—C1Me126.3 (3)
O2car—C2car-C2Me126.3 (3)125.8 (2)
O3car—C3car-C3Me125.5 (2)disordered
O4car—C4car-C4Me125.6 (3)126.8 (3)125.2 (3)
O6car—C6car-C6Me125.9 (3)125.8 (3)126.0 (2)
C1"—O1"—C2'114.18 (17)
C1'—O1'—C3113.13 (15)
Torsion angles (°)
C1—C2—C3—C4–52.8 (2)–47.7 (2)–49.6 (2)
C1—O5—C5—C458.0 (3)64.5 (2)63.9 (2)
O5—C1—O1—C1car79.8 (3)
C1—C2—O2—C2car–132.42 (19)–133.34 (19)
C2—C3—O3—C3car–73.1 (2)disordered
C3—C4—O4—C4car127.6 (2)129.7 (2)130.5 (2)
C5—C6—O6—C6car–155.8 (2)–172.0 (2)156.2 (2)
C1—O1—C1car—C1Me–170.8 (3)
C2—O2—C2car—C2Me174.93 (19)173.5 (2)
C3—O3—C3car—C3Me171.6 (2)disordered
C4—O4—C4car—C4Me–174.7 (2)–177.2 (2)–164.9 (2)
C6—O6—C6car—C6Me173.2 (3)–178.5 (2)172.9 (2)
O5—C5—C6—O6–65.5 (3) (gg)
O5'—C5'—C6'—O6'69.5 (2) (gt)
O5"—C5"—C6"—O6"60.5 (2) (gt)
C2"—C1"—O1"—C2'–152.08 (16)
C1"—O1"—C2'—C1'–92.1 (2)
C1"—O1"—C2'—C3'147.46 (16)
C2'—C1'—O1'—C3–163.29 (17)
C1'—O1'—C3—C2–126.53 (18)
C1'—O1'—C3—C4111.79 (19)
Notes: (a) subscripts `car' denote carbonyl C atoms, and subscripts `Me' denote methyl C atoms in an O-acetyl side chain. (b) R1, R2 and R3 refer to the three Man residues in (III) [see structure (III) in text for assignments]. gg = gauche–gauche and gt = gauche–trans.
Selected bond lengths, bond angles and torsion angles in αManOCH3, (IV)a top
Bond lengths (Å)Bond lengths (Å)
C1—C21.524C2—O21.415
C2—C31.529C3—O31.422
C3—C41.519C4—O41.430
C4—C51.529C5—O51.435
C5—C61.518C6—O61.413
C1—O11.400O1—CH31.423
C1—O51.415
Bond angles (°)
C5—O5—C1114.29C1—O1—CH3113.91
Torsion angles (°)
C1—C2—C3—C4-53.37
C1—O5—C5—C459.13
O5—C1—O1—CH360.51
O5—C5—C6—O6-65.10 (gg)
Note: (a) data taken from Jeffrey et al. (1977). gg = gauche–gauche.
Selected bond lengths, bond angles and torsion angles in Man2OCH3. (V) Original structure (Srikrishnan et al., 1989) and low-temperature redetermined structure (Zhang et al., 2018) [Zhang, W., Oliver, A. G. &amp; Serianni, A. S. (2018). CSD Communication. CCDC1883853. CCDC, Cambridge, England]. top
Structural ParameterR1aR2
Bond lengths (Å)
C1—C21.522 (1.522)b1.513 (1.520)
C2—C31.520 (1.524)1.521 (1.525)
C3—C41.517 (1.524)1.517 (1.517)
C4—C51.525 (1.534)1.517 (1.536)c
C5—C61.517 (1.521)1.517 (1.515)
C1—O11.397 (1.408)1.403 (1.411)
C1—O51.417 (1.413)1.411 (1.411)
C2—O21.432 (1.439)1.430 (1.432)
C3—O31.427 (1.423)1.416 (1.424)
C4—O41.430 (1.438)1.431 (1.429)
C5—O51.430 (1.436)1.447 (1.445)
C6—O61.439 (1.434)1.425 (1.426)
O1—CH31.428 (1.439)
Bond angles (°)
C5—O5—C1115.66 (115.57)
C5'—O5'—C1'115.65 (115.78)
C1'—O1'—C2114.02 (113.78)
C1—O1—CH3112.96 (112.29)
Torsion angles (°)
C1—C2—C3—C4-54.22 (-53.86)
C1—O5—C5—C449.74 (50.34)
C1'—C2'—C3'—C4'-53.72 (-54.39)
C1'—O5'—C5'—C4'54.73 (54.22)
C2—C1—O1—CH3 (φ)-177.67 (-178.83)
O5—C1—O1—CH3 (φ)60.09 (59.17)
H1—C1—O1—CH3 (φ)-53.92 (-61.61)
C2'—C1'—O1'—C2 (φ')-172.08 (-172.26)
O5'—C1'—O1'—C2 (φ')64.24 (64.33)
H1'—C1'—O1'—C2 (φ')-53.99 (-55.32)
C1'—O1'—C2—C1 (ψ')-105.30 (-104.08)
C1'—O1'—C2—C3 (ψ')136.12 (136.62)
C1'—O1'—C2—H2 (ψ')14.89 (16.99)
O5—C5—C6—O6-54.76 (-54.30) (gg)
O5'—C5'—C6'—O6'-67.43 (-66.88) (gg)
Notes: (a) R1 and R2 refer to the two αManp residues in disaccharide (V); see structure (V) in the text for assignments. The primed atoms in R2 are identified as unprimed for the bond lengths to simplify the table. (b) Values in parentheses pertain to the new low temperature X-ray structure redetermination of (V) solved in this study. (c) Values shown in bold font are those showing large differences between the two structures. gg = gauche–gauche.
List of 1H and 13C chemical shifts for compound (III). top
1H NMR (600 MHz, CDCl3)
δ: 2.01 (s, 3H), 2.05 (s, 6H), 2.08 (s, 3H), 2.10 (s, 3H), 2.12 (s, 3H), 2.13 (s, 3H), 2.14 (s, 3H), 2.16 (s, 6H), 2.23 (s, 3H), 3.91 (dd, J = 3.0, 2.1 Hz, 1H), 3.97 (m, 2H), 4.10 (dd, J = 12.6, 2.5 Hz, 1H), 4.11-4.24 (m, 6H), 4.26 (dd, J = 12.5, 5.1 Hz, 1H), 4.85 (d, J = 1.9 Hz, 1H), 5.13 (dd, J = 9.9, 3.1 Hz, 1H), 5.14 (d, J = 2.0 Hz, 1H), 5.26 (m, 2H), 5.30 (t, J = 10.0 Hz, 1H), 5.34 (t, J = 10.0 Hz, 2H), 5.39 (dd, J = 10.0, 3.3 Hz, 1H), 6.10 (d, J = 1.9 Hz, 1H)
13C NMR (150 MHz, CDCl3)
δ: 20.5, 20.6 (×2), 20.7, 20.7, 20.7 (×2), 20.7, 20.8, 20.8, 21.0, 62.0, 62.0, 62.5, 65.5, 66.3, 67.4, 68.3, 69.4, 69.4, 69.5, 69.5, 69.6, 70.5, 74.4, 77.9, 90.5, 99.6, 99.8, 167.8, 169.4 (×2), 169.5, 169.7, 169.8, 170.0, 170.2, 170.3, 170.6, 170.7.

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