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A complementary application of three analytical techniques, viz. multidimensional nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MS), and single-crystal X-ray diffractometry was required to identify and refine two natural products isolated from Millettia versicolor and solvent of crystallization. The two compounds, namely 3-(2H-1,3-benzodioxol-5-yl)-6-meth­oxy-8,8-dimethyl-4H,8H-pyrano[2,3-h]chromen-4-one, or durmillone, (I), and (2E)-1-(4-{[(2E)-3,7-di­methyl­octa-2,6-dien-1-yl]­oxy}-2-hydroxy­phen­yl)-3-(4-hy­droxy­phen­yl)prop-2-en-1-one, (II), could not be separated by routine column chromatography and cocrystallized in a 2:1 ratio with 0.13 mol­ecules of ethanol solvent. Compound (II) and ethanol could not be initially identified by single-crystal X-ray analysis due to complex disorder in the aliphatic chain region of (II). Mass spectrometry ensured that (II) represented only one species disordered over several positions in the solid state, rather than several species cohabitating on the same crystallographic site. The atomic identification and connectivity in (II) were established by several 2D (two-dimensional) NMR techniques, which in turn relied on a knowledge of its exact mass. The derived connectivity was then used in the single-crystal analysis to model the disorder of the aliphatic chain in (II) over three positions and allowed identification of a partially occupied ethanol solvent mol­ecule that was disordered over an inversion center. The disordered moieties were refined with restraints and constraints.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617014966/qs3066sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617014966/qs3066Isup2.hkl
Contains datablock I

CCDC reference: 1580102

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT-Plus (Bruker, 2016); data reduction: SAINT-Plus (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3-(2H-1,3-Benzodioxol-5-yl)-6-methoxy-8,8-dimethyl-4H,8H-pyrano[2,3-h]chromen-4-one– (2E)-1-(4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one–ethanol (2/1/0.13) top
Crystal data top
2C22H18O6·C25H28O4·0.13C2H6OZ = 2
Mr = 1155.42F(000) = 1219
Triclinic, P1Dx = 1.336 Mg m3
a = 12.519 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.594 (3) ÅCell parameters from 6163 reflections
c = 19.975 (4) Åθ = 2.5–25.2°
α = 80.12 (3)°µ = 0.10 mm1
β = 89.69 (3)°T = 100 K
γ = 68.02 (3)°Block, yellow
V = 2871.3 (12) Å30.11 × 0.06 × 0.02 mm
Data collection top
Bruker APEX II Quazar
diffractometer
11806 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs7371 reflections with I > 2σ(I)
Mirror optics monochromatorRint = 0.054
Detector resolution: 7.9 pixels mm-1θmax = 26.5°, θmin = 1.0°
0.5° ω and 0.5° φ scansh = 1515
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1515
Tmin = 0.679, Tmax = 0.745l = 2524
42663 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.165 w = 1/[σ2(Fo2) + (0.0815P)2 + 0.7244P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
11806 reflectionsΔρmax = 0.47 e Å3
871 parametersΔρmin = 0.55 e Å3
193 restraints
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)
O10.56890 (15)0.13223 (16)0.00339 (10)0.0432 (5)
O20.70046 (14)0.24504 (15)0.06278 (9)0.0368 (4)
O31.00320 (13)0.02748 (13)0.14992 (9)0.0293 (4)
O40.66409 (14)0.18670 (14)0.07879 (9)0.0353 (4)
O50.75708 (13)0.44891 (14)0.22375 (9)0.0337 (4)
O60.97623 (13)0.34022 (14)0.26052 (9)0.0341 (4)
C10.6006 (2)0.2377 (2)0.02497 (15)0.0434 (7)
H1A0.6188440.3066310.0118290.052*
H1B0.5364440.2339310.0553030.052*
C20.66991 (19)0.1149 (2)0.00882 (12)0.0285 (5)
C30.7481 (2)0.1809 (2)0.03163 (12)0.0307 (6)
C40.8545 (2)0.1757 (2)0.03981 (13)0.0354 (6)
H40.9067940.2186050.0690780.043*
C50.8824 (2)0.1037 (2)0.00280 (13)0.0332 (6)
H50.9558930.0983360.0069820.040*
C60.8059 (2)0.0394 (2)0.04013 (12)0.0281 (5)
C70.6956 (2)0.0442 (2)0.04540 (12)0.0286 (5)
H7A0.6411830.0001450.0733050.034*
C80.8440 (2)0.0263 (2)0.08318 (12)0.0276 (5)
C90.9531 (2)0.0215 (2)0.11070 (12)0.0286 (5)
H9A0.9994260.0963130.1019030.034*
C100.9372 (2)0.1349 (2)0.16427 (12)0.0275 (5)
C110.82200 (19)0.1910 (2)0.14116 (12)0.0270 (5)
C120.7671 (2)0.1389 (2)0.09904 (13)0.0286 (5)
C130.7590 (2)0.2988 (2)0.16075 (13)0.0287 (5)
H130.6796740.3385080.1462230.034*
C140.8110 (2)0.3469 (2)0.20055 (13)0.0291 (5)
C150.6354 (2)0.5050 (2)0.20840 (16)0.0410 (7)
H15A0.6194720.5273430.1589200.061*
H15B0.6054610.5748010.2291270.061*
H15C0.5977870.4515180.2266120.061*
C160.9300 (2)0.2893 (2)0.22067 (12)0.0284 (5)
C170.99329 (19)0.1816 (2)0.20388 (12)0.0273 (5)
C181.1118 (2)0.1207 (2)0.23238 (13)0.0334 (6)
H181.1532490.0420390.2280840.040*
C191.1612 (2)0.1760 (2)0.26440 (14)0.0386 (7)
H191.2360480.1338750.2862570.046*
C201.1028 (2)0.3033 (2)0.26724 (15)0.0398 (7)
C211.1258 (2)0.3311 (3)0.33547 (17)0.0508 (8)
H21A1.0790240.4128590.3366500.076*
H21B1.2077730.3175510.3416870.076*
H21C1.1054710.2808690.3720980.076*
C221.1381 (2)0.3742 (2)0.20857 (18)0.0540 (9)
H22A1.1130830.3611480.1653640.081*
H22B1.2222090.3503220.2113830.081*
H22C1.1017680.4570960.2110320.081*
O1A0.79383 (15)0.55491 (14)0.44566 (9)0.0376 (4)
O2A0.90429 (14)0.47814 (14)0.54799 (9)0.0338 (4)
O3A0.98022 (13)0.01385 (13)0.34200 (8)0.0299 (4)
O4A0.68874 (14)0.27032 (14)0.35312 (9)0.0353 (4)
O5A0.58184 (13)0.02020 (14)0.20800 (9)0.0324 (4)
O6A0.77140 (13)0.16003 (13)0.20853 (8)0.0298 (4)
C1A0.8164 (2)0.5802 (2)0.51056 (13)0.0364 (6)
H1AA0.8425500.6462190.5038830.044*
H1AB0.7453500.6016870.5357570.044*
C2A0.8450 (2)0.4352 (2)0.45289 (13)0.0296 (6)
C3A0.9101 (2)0.3899 (2)0.51380 (13)0.0291 (5)
C4A0.9707 (2)0.2733 (2)0.53390 (13)0.0308 (6)
H4A1.0169270.2426210.5755230.037*
C5A0.9614 (2)0.2010 (2)0.49004 (12)0.0296 (6)
H5A1.0005970.1191140.5030250.035*
C6A0.89666 (19)0.2453 (2)0.42816 (12)0.0277 (5)
C7A0.8371 (2)0.3669 (2)0.40805 (13)0.0310 (6)
H7AA0.7937790.3996800.3655500.037*
C8A0.8879 (2)0.16453 (19)0.38420 (12)0.0278 (5)
C9A0.9806 (2)0.0690 (2)0.37731 (12)0.0292 (5)
H9AA1.0520040.0589260.3989620.035*
C10A0.87817 (19)0.00108 (19)0.30995 (12)0.0262 (5)
C11A0.77769 (19)0.09522 (19)0.31192 (12)0.0260 (5)
C12A0.7781 (2)0.1837 (2)0.34963 (13)0.0290 (5)
C13A0.6763 (2)0.1053 (2)0.27681 (12)0.0279 (5)
H13A0.6077890.1721580.2765540.033*
C14A0.67513 (19)0.0199 (2)0.24300 (12)0.0270 (5)
C15A0.4798 (2)0.1244 (2)0.20150 (14)0.0372 (6)
H15D0.4189700.1162610.1746650.056*
H15E0.4971580.1908530.1785590.056*
H15F0.4537370.1372830.2468250.056*
C16A0.7777 (2)0.07962 (19)0.24395 (12)0.0266 (5)
C17A0.8803 (2)0.08961 (19)0.27518 (12)0.0267 (5)
C18A0.9849 (2)0.1868 (2)0.26507 (13)0.0314 (6)
H18A1.0587710.1882490.2771460.038*
C19A0.9753 (2)0.2732 (2)0.23875 (13)0.0333 (6)
H19A1.0431510.3327960.2283540.040*
C20A0.8599 (2)0.2789 (2)0.22507 (13)0.0315 (6)
C21A0.8545 (2)0.3305 (2)0.16251 (13)0.0364 (6)
H21D0.7752490.3238360.1531190.055*
H21E0.9061530.4128200.1706470.055*
H21F0.8785760.2882980.1233530.055*
C22A0.8254 (2)0.3424 (2)0.28855 (14)0.0382 (6)
H22D0.8258180.3035530.3270170.057*
H22E0.8805210.4233020.2992460.057*
H22F0.7478560.3410440.2800850.057*
O70.53894 (15)1.63181 (14)0.67718 (10)0.0380 (4)
H70.4683121.6713040.6676390.057*
O80.78105 (14)1.01492 (14)0.51723 (9)0.0370 (4)
O90.76654 (14)0.86116 (14)0.45556 (10)0.0388 (5)
H90.7977430.8926450.4787730.058*
C230.5718 (2)1.53663 (19)0.64682 (12)0.0282 (5)
C240.6866 (2)1.4602 (2)0.65693 (13)0.0314 (6)
H240.7395341.4751830.6841380.038*
C250.7233 (2)1.3625 (2)0.62722 (12)0.0293 (6)
H250.8020161.3111650.6341100.035*
C260.64824 (19)1.33647 (19)0.58729 (12)0.0272 (5)
C270.5329 (2)1.4154 (2)0.57716 (13)0.0301 (6)
H270.4798991.4007920.5497850.036*
C280.4954 (2)1.5138 (2)0.60640 (12)0.0304 (6)
H280.4170691.5662260.5989090.036*
C290.6899 (2)1.2295 (2)0.55953 (12)0.0295 (6)
H290.7683981.1798340.5708140.035*
C300.6292 (2)1.1936 (2)0.51978 (12)0.0298 (6)
H300.5514871.2427650.5055770.036*
C310.6789 (2)1.0812 (2)0.49754 (13)0.0291 (5)
C320.61076 (19)1.0458 (2)0.45356 (12)0.0269 (5)
C330.65832 (19)0.9360 (2)0.43389 (13)0.0288 (5)
C340.5966 (2)0.8986 (2)0.39197 (12)0.0284 (5)
H340.6305980.8240250.3797030.034*
C350.4854 (2)0.9712 (2)0.36846 (12)0.0291 (5)
C360.4349 (2)1.0800 (2)0.38788 (13)0.0340 (6)
H360.3575821.1288810.3725850.041*
O100.41744 (14)0.94625 (14)0.32554 (9)0.0337 (4)
C370.4967 (2)1.1160 (2)0.42881 (13)0.0314 (6)
H370.4614891.1905760.4409110.038*
C380.4684 (2)0.8399 (2)0.29848 (13)0.0325 (6)
H38A0.4972030.7716540.3359940.039*
H38B0.5338260.8420040.2709630.039*
C390.3756 (2)0.8323 (2)0.25516 (13)0.0380 (6)
H390.3114230.8239630.2777640.046*
C400.3734 (2)0.8359 (2)0.18817 (13)0.0340 (6)
C410.4659 (3)0.8484 (3)0.14387 (15)0.0494 (8)
H41A0.5244340.8595670.1710550.074*
H41B0.4321720.9158450.1070960.074*
H41C0.5017150.7778880.1243380.074*
C420.2788 (4)0.8119 (7)0.1549 (6)0.043 (3)0.497 (3)
H42A0.2542490.8648540.1102860.052*0.497 (3)
H42B0.2117140.8313180.1834900.052*0.497 (3)
C430.3112 (6)0.6851 (5)0.1436 (3)0.0511 (18)0.497 (3)
H43A0.3830650.6637990.1190400.061*0.497 (3)
H43B0.3293530.6335530.1887870.061*0.497 (3)
C440.2272 (5)0.6590 (7)0.1066 (4)0.060 (2)0.497 (3)
H440.1507590.6895190.1206510.072*0.497 (3)
C450.2398 (5)0.5993 (6)0.0561 (4)0.047 (2)0.497 (3)
C460.3505 (6)0.5504 (6)0.0255 (4)0.066 (2)0.497 (3)
H46A0.3758910.6133720.0062160.099*0.497 (3)
H46B0.3410250.5104310.0106980.099*0.497 (3)
H46C0.4083220.4948960.0604350.099*0.497 (3)
C470.1410 (8)0.5804 (10)0.0233 (7)0.049 (3)0.497 (3)
H47A0.1351900.5083350.0474400.073*0.497 (3)
H47B0.1552580.5743420.0244860.073*0.497 (3)
H47C0.0686810.6462270.0256250.073*0.497 (3)
C42A0.2725 (4)0.8328 (9)0.1487 (6)0.060 (4)0.234 (3)
H42C0.2284840.9097100.1201880.072*0.234 (3)
H42D0.2199340.8095940.1796760.072*0.234 (3)
C43A0.3301 (8)0.7399 (9)0.1038 (6)0.0380 (6)0.234 (3)
H43C0.3682360.7741490.0675670.046*0.234 (3)
H43D0.3916910.6734850.1324960.046*0.234 (3)
C44A0.2578 (11)0.6938 (8)0.0713 (6)0.049 (3)0.234 (3)
H44A0.2043620.7506830.0372740.058*0.234 (3)
C45A0.2486 (12)0.5905 (8)0.0780 (10)0.052 (5)0.234 (3)
C46A0.3343 (12)0.4821 (9)0.1161 (7)0.057 (4)0.234 (3)
H46D0.4114490.4846050.1123030.085*0.234 (3)
H46E0.3320340.4159110.0973980.085*0.234 (3)
H46F0.3167240.4733260.1641390.085*0.234 (3)
C47A0.156 (2)0.5714 (18)0.0387 (16)0.054 (7)0.234 (3)
H47D0.0865510.5876040.0645770.081*0.234 (3)
H47E0.1841130.4904410.0319260.081*0.234 (3)
H47F0.1371800.6237730.0055880.081*0.234 (3)
C42B0.2725 (4)0.8328 (9)0.1487 (6)0.060 (4)0.269 (2)
H42E0.2253870.9138210.1266990.072*0.269 (2)
H42F0.2243830.8070460.1820170.072*0.269 (2)
C43B0.2952 (9)0.7563 (6)0.0930 (4)0.0380 (6)0.269 (2)
H43E0.2240640.7772420.0638220.046*0.269 (2)
H43F0.3561950.7667400.0639390.046*0.269 (2)
C44B0.3320 (9)0.6372 (6)0.1293 (5)0.0467 (18)0.269 (2)
H44B0.3162130.6216550.1757660.056*0.269 (2)
C45B0.3881 (8)0.5498 (6)0.0974 (5)0.0467 (18)0.269 (2)
C46B0.4063 (9)0.4373 (7)0.1404 (6)0.0467 (18)0.269 (2)
H46G0.3947620.4473790.1878570.070*0.269 (2)
H46H0.4851190.3826110.1369380.070*0.269 (2)
H46I0.3511090.4065390.1253340.070*0.269 (2)
C47B0.4474 (11)0.5457 (10)0.0310 (5)0.069 (3)0.269 (2)
H47G0.4300970.6251940.0064340.104*0.269 (2)
H47H0.4194730.5034900.0029700.104*0.269 (2)
H47I0.5310090.5056440.0405630.104*0.269 (2)
O110.0152 (18)0.5008 (18)0.0211 (8)0.079 (6)*0.1346 (12)
H110.0146630.4869480.0637440.119*0.1346
C480.079 (2)0.541 (2)0.0006 (10)0.059 (6)*0.1346 (12)
H48A0.1542640.4801770.0190820.071*0.1346 (12)
H48B0.0685350.6125480.0182240.071*0.1346 (12)
C490.074 (2)0.564 (2)0.0753 (9)0.070 (7)*0.1346 (12)
H49A0.1362850.5899580.0906490.105*0.1346
H49B0.0006110.6251480.0929750.105*0.1346
H49C0.0832070.4928060.0921520.105*0.1346
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0341 (10)0.0472 (11)0.0551 (13)0.0181 (8)0.0028 (9)0.0208 (10)
O20.0325 (9)0.0461 (11)0.0394 (11)0.0188 (8)0.0012 (8)0.0184 (9)
O30.0240 (8)0.0278 (8)0.0389 (10)0.0094 (7)0.0020 (7)0.0143 (8)
O40.0263 (9)0.0346 (9)0.0462 (11)0.0121 (7)0.0046 (8)0.0095 (8)
O50.0254 (8)0.0276 (9)0.0470 (11)0.0061 (7)0.0005 (8)0.0134 (8)
O60.0249 (8)0.0351 (9)0.0448 (11)0.0098 (7)0.0006 (8)0.0180 (8)
C10.0394 (15)0.0485 (17)0.0477 (18)0.0208 (13)0.0050 (13)0.0135 (14)
C20.0245 (12)0.0306 (12)0.0317 (14)0.0119 (10)0.0025 (10)0.0059 (11)
C30.0345 (13)0.0315 (13)0.0287 (14)0.0144 (11)0.0030 (11)0.0075 (11)
C40.0349 (14)0.0421 (15)0.0330 (15)0.0150 (11)0.0054 (12)0.0156 (12)
C50.0312 (13)0.0382 (14)0.0353 (15)0.0175 (11)0.0032 (11)0.0101 (12)
C60.0301 (12)0.0295 (12)0.0269 (13)0.0140 (10)0.0002 (10)0.0044 (10)
C70.0266 (12)0.0290 (12)0.0307 (14)0.0106 (10)0.0016 (10)0.0064 (11)
C80.0278 (12)0.0309 (12)0.0281 (13)0.0151 (10)0.0039 (10)0.0064 (10)
C90.0285 (12)0.0288 (12)0.0337 (14)0.0146 (10)0.0043 (11)0.0106 (11)
C100.0274 (12)0.0266 (12)0.0304 (14)0.0112 (10)0.0043 (10)0.0081 (10)
C110.0246 (12)0.0290 (12)0.0298 (14)0.0123 (10)0.0034 (10)0.0067 (10)
C120.0278 (13)0.0298 (12)0.0316 (14)0.0149 (10)0.0027 (11)0.0055 (11)
C130.0246 (12)0.0267 (12)0.0351 (14)0.0101 (10)0.0012 (10)0.0054 (11)
C140.0290 (12)0.0257 (12)0.0325 (14)0.0094 (10)0.0031 (11)0.0069 (11)
C150.0258 (13)0.0349 (14)0.0602 (19)0.0066 (11)0.0000 (12)0.0146 (13)
C160.0264 (12)0.0312 (13)0.0323 (14)0.0143 (10)0.0017 (10)0.0099 (11)
C170.0241 (11)0.0290 (12)0.0323 (14)0.0119 (10)0.0038 (10)0.0108 (11)
C180.0242 (12)0.0327 (13)0.0438 (16)0.0076 (10)0.0013 (11)0.0152 (12)
C190.0251 (12)0.0384 (14)0.0520 (18)0.0071 (11)0.0029 (12)0.0188 (13)
C200.0213 (12)0.0396 (15)0.0621 (19)0.0096 (11)0.0019 (12)0.0232 (14)
C210.0312 (14)0.0486 (17)0.074 (2)0.0063 (12)0.0108 (14)0.0347 (16)
C220.0338 (15)0.0433 (16)0.091 (3)0.0161 (13)0.0123 (16)0.0250 (17)
O1A0.0471 (11)0.0268 (9)0.0373 (11)0.0102 (8)0.0005 (8)0.0106 (8)
O2A0.0363 (9)0.0308 (9)0.0354 (10)0.0109 (7)0.0004 (8)0.0133 (8)
O3A0.0265 (8)0.0270 (8)0.0351 (10)0.0071 (7)0.0033 (7)0.0095 (7)
O4A0.0286 (9)0.0283 (9)0.0459 (11)0.0040 (7)0.0004 (8)0.0142 (8)
O5A0.0254 (8)0.0349 (9)0.0363 (10)0.0097 (7)0.0029 (7)0.0084 (8)
O6A0.0314 (9)0.0247 (8)0.0335 (10)0.0097 (7)0.0021 (7)0.0077 (7)
C1A0.0416 (15)0.0288 (13)0.0365 (15)0.0093 (11)0.0007 (12)0.0094 (11)
C2A0.0292 (12)0.0237 (12)0.0367 (15)0.0104 (10)0.0038 (11)0.0070 (11)
C3A0.0275 (12)0.0318 (13)0.0333 (14)0.0139 (10)0.0063 (11)0.0142 (11)
C4A0.0270 (12)0.0337 (13)0.0315 (14)0.0098 (10)0.0004 (11)0.0092 (11)
C5A0.0273 (12)0.0278 (12)0.0327 (14)0.0081 (10)0.0038 (11)0.0086 (11)
C6A0.0264 (12)0.0271 (12)0.0301 (14)0.0086 (10)0.0014 (10)0.0099 (10)
C7A0.0309 (13)0.0308 (13)0.0311 (14)0.0115 (10)0.0006 (11)0.0052 (11)
C8A0.0309 (12)0.0247 (12)0.0275 (13)0.0097 (10)0.0010 (10)0.0058 (10)
C9A0.0300 (12)0.0282 (12)0.0307 (14)0.0114 (10)0.0028 (11)0.0073 (11)
C10A0.0255 (12)0.0244 (12)0.0270 (13)0.0086 (9)0.0006 (10)0.0020 (10)
C11A0.0267 (12)0.0228 (11)0.0285 (13)0.0091 (9)0.0037 (10)0.0055 (10)
C12A0.0293 (12)0.0245 (12)0.0312 (14)0.0082 (10)0.0039 (11)0.0043 (10)
C13A0.0262 (12)0.0261 (12)0.0303 (14)0.0088 (10)0.0032 (10)0.0051 (10)
C14A0.0239 (12)0.0301 (12)0.0266 (13)0.0105 (10)0.0011 (10)0.0039 (10)
C15A0.0268 (13)0.0385 (14)0.0405 (16)0.0070 (11)0.0039 (11)0.0038 (12)
C16A0.0305 (12)0.0254 (12)0.0255 (13)0.0122 (10)0.0016 (10)0.0055 (10)
C17A0.0299 (12)0.0229 (11)0.0266 (13)0.0095 (9)0.0018 (10)0.0041 (10)
C18A0.0269 (12)0.0293 (13)0.0356 (15)0.0078 (10)0.0020 (11)0.0064 (11)
C19A0.0327 (13)0.0270 (12)0.0358 (15)0.0057 (10)0.0006 (11)0.0073 (11)
C20A0.0348 (13)0.0229 (12)0.0346 (15)0.0078 (10)0.0008 (11)0.0067 (11)
C21A0.0414 (15)0.0296 (13)0.0390 (16)0.0119 (11)0.0005 (12)0.0121 (12)
C22A0.0438 (15)0.0297 (13)0.0397 (16)0.0127 (11)0.0025 (13)0.0055 (12)
O70.0334 (9)0.0304 (9)0.0498 (12)0.0076 (7)0.0023 (9)0.0167 (9)
O80.0269 (9)0.0322 (9)0.0495 (12)0.0053 (7)0.0022 (8)0.0146 (8)
O90.0280 (9)0.0296 (9)0.0547 (13)0.0036 (7)0.0087 (8)0.0140 (8)
C230.0323 (13)0.0231 (12)0.0297 (14)0.0103 (10)0.0031 (11)0.0065 (10)
C240.0278 (12)0.0315 (13)0.0377 (15)0.0140 (10)0.0014 (11)0.0072 (11)
C250.0242 (12)0.0277 (12)0.0348 (14)0.0091 (10)0.0035 (11)0.0044 (11)
C260.0256 (12)0.0259 (12)0.0287 (13)0.0086 (9)0.0049 (10)0.0040 (10)
C270.0271 (12)0.0287 (12)0.0329 (14)0.0080 (10)0.0020 (11)0.0070 (11)
C280.0274 (12)0.0290 (12)0.0313 (14)0.0066 (10)0.0015 (11)0.0061 (11)
C290.0244 (12)0.0274 (12)0.0349 (14)0.0073 (10)0.0053 (11)0.0071 (11)
C300.0264 (12)0.0269 (12)0.0323 (14)0.0059 (10)0.0010 (11)0.0053 (11)
C310.0260 (12)0.0291 (12)0.0311 (14)0.0089 (10)0.0039 (10)0.0064 (11)
C320.0254 (12)0.0276 (12)0.0281 (13)0.0100 (10)0.0050 (10)0.0066 (10)
C330.0247 (12)0.0276 (12)0.0324 (14)0.0082 (10)0.0015 (10)0.0050 (11)
C340.0316 (13)0.0251 (12)0.0286 (14)0.0098 (10)0.0030 (11)0.0076 (10)
C350.0315 (13)0.0334 (13)0.0233 (13)0.0139 (10)0.0029 (10)0.0042 (11)
C360.0308 (13)0.0343 (13)0.0304 (14)0.0047 (11)0.0015 (11)0.0064 (11)
O100.0333 (9)0.0350 (9)0.0331 (10)0.0112 (7)0.0020 (8)0.0110 (8)
C370.0316 (13)0.0294 (13)0.0309 (14)0.0078 (10)0.0028 (11)0.0082 (11)
C380.0362 (13)0.0317 (13)0.0311 (14)0.0138 (11)0.0026 (11)0.0077 (11)
C390.0389 (14)0.0459 (14)0.0363 (14)0.0236 (12)0.0034 (11)0.0089 (12)
C400.0326 (13)0.0280 (13)0.0374 (15)0.0060 (10)0.0002 (11)0.0081 (11)
C410.0530 (18)0.0602 (19)0.0348 (16)0.0204 (15)0.0053 (14)0.0107 (14)
C420.038 (5)0.049 (4)0.038 (5)0.009 (3)0.005 (4)0.013 (4)
C430.057 (4)0.032 (3)0.068 (5)0.020 (3)0.020 (3)0.009 (3)
C440.037 (3)0.067 (5)0.086 (6)0.021 (3)0.003 (3)0.036 (4)
C450.038 (4)0.046 (4)0.055 (6)0.012 (3)0.003 (3)0.013 (3)
C460.070 (4)0.071 (5)0.065 (5)0.028 (4)0.018 (4)0.034 (4)
C470.037 (4)0.053 (6)0.061 (8)0.018 (4)0.011 (4)0.019 (5)
C42A0.039 (5)0.091 (7)0.055 (7)0.019 (4)0.003 (4)0.041 (6)
C43A0.0389 (14)0.0459 (14)0.0363 (14)0.0236 (12)0.0034 (11)0.0089 (12)
C44A0.083 (10)0.047 (6)0.038 (7)0.048 (7)0.016 (6)0.011 (6)
C45A0.086 (12)0.045 (7)0.041 (11)0.043 (7)0.006 (7)0.008 (7)
C46A0.071 (9)0.058 (7)0.055 (9)0.042 (7)0.011 (7)0.000 (6)
C47A0.085 (15)0.031 (9)0.045 (12)0.027 (9)0.032 (9)0.006 (7)
C42B0.039 (5)0.091 (7)0.055 (7)0.019 (4)0.003 (4)0.041 (6)
C43B0.0389 (14)0.0459 (14)0.0363 (14)0.0236 (12)0.0034 (11)0.0089 (12)
C44B0.036 (3)0.029 (3)0.073 (5)0.013 (3)0.019 (3)0.003 (3)
C45B0.036 (3)0.029 (3)0.073 (5)0.013 (3)0.019 (3)0.003 (3)
C46B0.036 (3)0.029 (3)0.073 (5)0.013 (3)0.019 (3)0.003 (3)
C47B0.074 (9)0.059 (8)0.078 (8)0.043 (7)0.017 (6)0.019 (6)
Geometric parameters (Å, º) top
O1—C11.451 (3)C23—C281.394 (3)
O1—C21.369 (3)C24—H240.9500
O2—C11.439 (3)C24—C251.379 (3)
O2—C31.390 (3)C25—H250.9500
O3—C91.359 (3)C25—C261.397 (3)
O3—C101.374 (3)C26—C271.405 (3)
O4—C121.237 (3)C26—C291.457 (3)
O5—C141.369 (3)C27—H270.9500
O5—C151.428 (3)C27—C281.381 (3)
O6—C161.356 (3)C28—H280.9500
O6—C201.475 (3)C29—H290.9500
C1—H1A0.9900C29—C301.341 (3)
C1—H1B0.9900C30—H300.9500
C2—C31.384 (3)C30—C311.463 (3)
C2—C71.367 (3)C31—C321.459 (3)
C3—C41.365 (3)C32—C331.409 (3)
C4—H40.9500C32—C371.407 (3)
C4—C51.400 (4)C33—C341.391 (3)
C5—H50.9500C34—H340.9500
C5—C61.399 (3)C34—C351.379 (3)
C6—C71.407 (3)C35—C361.399 (3)
C6—C81.481 (3)C35—O101.363 (3)
C7—H7A0.9500C36—H360.9500
C8—C91.345 (3)C36—C371.367 (3)
C8—C121.472 (3)O10—C381.449 (3)
C9—H9A0.9500C37—H370.9500
C10—C111.388 (3)C38—H38A0.9900
C10—C171.393 (3)C38—H38B0.9900
C11—C121.464 (3)C38—C391.494 (4)
C11—C131.412 (3)C39—H390.9500
C13—H130.9500C39—C401.331 (3)
C13—C141.374 (3)C40—C411.491 (4)
C14—C161.416 (3)C40—C421.510 (4)
C15—H15A0.9800C40—C42A1.510 (4)
C15—H15B0.9800C40—C42B1.510 (4)
C15—H15C0.9800C41—H41A0.9800
C16—C171.389 (3)C41—H41B0.9800
C17—C181.456 (3)C41—H41C0.9800
C18—H180.9500C42—H42A0.9900
C18—C191.326 (4)C42—H42B0.9900
C19—H190.9500C42—C431.551 (6)
C19—C201.504 (3)C42—C43B1.500 (10)
C20—C211.518 (4)C43—H43A0.9900
C20—C221.515 (4)C43—H43B0.9900
C21—H21A0.9800C43—C441.453 (6)
C21—H21B0.9800C43—C42B1.759 (11)
C21—H21C0.9800C43—C43B1.192 (11)
C22—H22A0.9800C43—C44B0.673 (8)
C22—H22B0.9800C43—C45B1.996 (9)
C22—H22C0.9800C44—H440.9500
O1A—C1A1.441 (3)C44—C451.332 (4)
O1A—C2A1.382 (3)C44—C43B1.722 (12)
O2A—C1A1.429 (3)C44—C44B1.303 (13)
O2A—C3A1.380 (3)C44—C45B1.997 (10)
O3A—C9A1.357 (3)C45—C461.468 (8)
O3A—C10A1.374 (3)C45—C471.518 (7)
O4A—C12A1.248 (3)C45—C45B1.867 (11)
O5A—C14A1.363 (3)C46—H46A0.9800
O5A—C15A1.435 (3)C46—H46B0.9800
O6A—C16A1.356 (3)C46—H46C0.9800
O6A—C20A1.473 (3)C46—C45B1.511 (12)
C1A—H1AA0.9900C46—C47B1.197 (13)
C1A—H1AB0.9900C47—H47A0.9800
C2A—C3A1.377 (3)C47—H47B0.9800
C2A—C7A1.371 (3)C47—H47C0.9800
C3A—C4A1.364 (3)C47—C481.20 (3)
C4A—H4A0.9500C42A—H42C0.9900
C4A—C5A1.402 (3)C42A—H42D0.9900
C5A—H5A0.9500C42A—C43A1.554 (6)
C5A—C6A1.390 (3)C43A—H43C0.9900
C6A—C7A1.414 (3)C43A—H43D0.9900
C6A—C8A1.486 (3)C43A—C44A1.452 (6)
C7A—H7AA0.9500C44A—H44A0.9500
C8A—C9A1.351 (3)C44A—C45A1.332 (4)
C8A—C12A1.458 (3)C45A—C46A1.467 (8)
C9A—H9AA0.9500C45A—C47A1.518 (7)
C10A—C11A1.389 (3)C46A—H46D0.9800
C10A—C17A1.403 (3)C46A—H46E0.9800
C11A—C12A1.450 (3)C46A—H46F0.9800
C11A—C13A1.406 (3)C47A—H47D0.9800
C13A—H13A0.9500C47A—H47E0.9800
C13A—C14A1.369 (3)C47A—H47F0.9800
C14A—C16A1.417 (3)C42B—H42E0.9900
C15A—H15D0.9800C42B—H42F0.9900
C15A—H15E0.9800C42B—C43B1.551 (6)
C15A—H15F0.9800C43B—H43E0.9900
C16A—C17A1.384 (3)C43B—H43F0.9900
C17A—C18A1.461 (3)C43B—C44B1.450 (6)
C18A—H18A0.9500C44B—H44B0.9500
C18A—C19A1.330 (3)C44B—C45B1.330 (4)
C19A—H19A0.9500C45B—C46B1.464 (8)
C19A—C20A1.502 (4)C45B—C47B1.516 (7)
C20A—C21A1.517 (3)C46B—H46G0.9800
C20A—C22A1.529 (4)C46B—H46H0.9800
C21A—H21D0.9800C46B—H46I0.9800
C21A—H21E0.9800C47B—H47G0.9800
C21A—H21F0.9800C47B—H47H0.9800
C22A—H22D0.9800C47B—H47I0.9800
C22A—H22E0.9800O11—H110.8400
C22A—H22F0.9800O11—C481.47 (3)
O7—H70.8400C48—H48A0.9900
O7—C231.361 (3)C48—H48B0.9900
O8—C311.257 (3)C48—C491.491 (17)
O9—H90.8400C49—H49A0.9800
O9—C331.350 (3)C49—H49B0.9800
C23—C241.391 (3)C49—H49C0.9800
C2—O1—C1104.48 (18)C38—C39—H39116.6
C3—O2—C1102.90 (19)C40—C39—C38126.7 (3)
C9—O3—C10118.00 (18)C40—C39—H39116.6
C14—O5—C15116.40 (19)C39—C40—C41124.6 (3)
C16—O6—C20118.84 (18)C39—C40—C42118.6 (5)
O1—C1—H1A110.5C39—C40—C42A122.5 (5)
O1—C1—H1B110.5C39—C40—C42B122.5 (5)
O2—C1—O1106.3 (2)C41—C40—C42116.4 (5)
O2—C1—H1A110.5C41—C40—C42A112.9 (5)
O2—C1—H1B110.5C41—C40—C42B112.9 (5)
H1A—C1—H1B108.7C42B—C40—C429.6 (7)
O1—C2—C3108.6 (2)C40—C41—H41A109.5
C7—C2—O1129.0 (2)C40—C41—H41B109.5
C7—C2—C3122.4 (2)C40—C41—H41C109.5
C2—C3—O2110.7 (2)H41A—C41—H41B109.5
C4—C3—O2127.3 (2)H41A—C41—H41C109.5
C4—C3—C2121.9 (2)H41B—C41—H41C109.5
C3—C4—H4121.8C40—C42—H42A108.4
C3—C4—C5116.5 (2)C40—C42—H42B108.4
C5—C4—H4121.8C40—C42—C43115.5 (4)
C4—C5—H5118.8H42A—C42—H42B107.5
C6—C5—C4122.4 (2)C43—C42—H42A108.4
C6—C5—H5118.8C43—C42—H42B108.4
C5—C6—C7119.3 (2)C43B—C42—C40122.8 (7)
C5—C6—C8120.0 (2)C43B—C42—H42A63.1
C7—C6—C8120.5 (2)C43B—C42—H42B128.5
C2—C7—C6117.4 (2)C43B—C42—C4346.0 (5)
C2—C7—H7A121.3C42—C43—H43A107.8
C6—C7—H7A121.3C42—C43—H43B107.8
C9—C8—C6118.2 (2)C42—C43—C42B5.0 (7)
C9—C8—C12118.7 (2)C42—C43—C45B154.9 (7)
C12—C8—C6123.1 (2)H43A—C43—H43B107.1
O3—C9—H9A117.0C44—C43—C42118.1 (5)
C8—C9—O3126.1 (2)C44—C43—H43A107.8
C8—C9—H9A117.0C44—C43—H43B107.8
O3—C10—C11121.4 (2)C44—C43—C42B115.2 (5)
O3—C10—C17115.6 (2)C44—C43—C45B68.7 (4)
C11—C10—C17123.0 (2)C42B—C43—H43A105.7
C10—C11—C12121.0 (2)C42B—C43—H43B112.8
C10—C11—C13117.8 (2)C42B—C43—C45B151.0 (7)
C13—C11—C12121.2 (2)C43B—C43—C4264.8 (6)
O4—C12—C8123.3 (2)C43B—C43—H43A72.1
O4—C12—C11122.0 (2)C43B—C43—H43B171.1
C11—C12—C8114.7 (2)C43B—C43—C4480.6 (6)
C11—C13—H13119.6C43B—C43—C42B59.8 (5)
C14—C13—C11120.9 (2)C43B—C43—C45B94.5 (5)
C14—C13—H13119.6C44B—C43—C42161.0 (15)
O5—C14—C13125.4 (2)C44B—C43—H43A56.5
O5—C14—C16115.0 (2)C44B—C43—H43B88.4
C13—C14—C16119.6 (2)C44B—C43—C4463.7 (11)
O5—C15—H15A109.5C44B—C43—C42B156.7 (14)
O5—C15—H15B109.5C44B—C43—C43B98.2 (12)
O5—C15—H15C109.5C44B—C43—C45B7.0 (12)
H15A—C15—H15B109.5C45B—C43—H43A49.5
H15A—C15—H15C109.5C45B—C43—H43B91.3
H15B—C15—H15C109.5C43—C44—H44114.7
O6—C16—C14117.0 (2)C43—C44—C43B43.1 (4)
O6—C16—C17122.1 (2)C43—C44—C45B68.6 (4)
C17—C16—C14120.7 (2)C45—C44—C43130.6 (6)
C10—C17—C18123.8 (2)C45—C44—H44114.7
C16—C17—C10117.9 (2)C45—C44—C43B112.1 (7)
C16—C17—C18118.2 (2)C45—C44—C45B64.7 (4)
C17—C18—H18120.3C43B—C44—H44115.1
C19—C18—C17119.4 (2)C43B—C44—C45B80.2 (4)
C19—C18—H18120.3C44B—C44—C4327.6 (4)
C18—C19—H19118.9C44B—C44—H44138.7
C18—C19—C20122.2 (2)C44B—C44—C45105.0 (6)
C20—C19—H19118.9C44B—C44—C43B55.2 (4)
O6—C20—C19110.8 (2)C44B—C44—C45B41.2 (3)
O6—C20—C21104.1 (2)C45B—C44—H44161.6
O6—C20—C22107.8 (2)C44—C45—C46122.5 (6)
C19—C20—C21112.6 (2)C44—C45—C47123.4 (7)
C19—C20—C22109.3 (2)C44—C45—C45B75.2 (4)
C22—C20—C21112.0 (2)C46—C45—C47114.1 (6)
C20—C21—H21A109.5C46—C45—C45B52.2 (5)
C20—C21—H21B109.5C47—C45—C45B153.8 (6)
C20—C21—H21C109.5C45—C46—H46A109.5
H21A—C21—H21B109.5C45—C46—H46B109.5
H21A—C21—H21C109.5C45—C46—H46C109.5
H21B—C21—H21C109.5C45—C46—C45B77.6 (5)
C20—C22—H22A109.5H46A—C46—H46B109.5
C20—C22—H22B109.5H46A—C46—H46C109.5
C20—C22—H22C109.5H46B—C46—H46C109.5
H22A—C22—H22B109.5C45B—C46—H46A92.8
H22A—C22—H22C109.5C45B—C46—H46B151.7
H22B—C22—H22C109.5C45B—C46—H46C44.4
C2A—O1A—C1A105.10 (19)C47B—C46—C45139.3 (7)
C3A—O2A—C1A105.00 (18)C47B—C46—H46A55.4
C9A—O3A—C10A118.46 (17)C47B—C46—H46B111.3
C14A—O5A—C15A116.10 (19)C47B—C46—H46C56.5
C16A—O6A—C20A118.02 (18)C47B—C46—C45B66.9 (6)
O1A—C1A—H1AA110.1C45—C47—H47A109.5
O1A—C1A—H1AB110.1C45—C47—H47B109.5
O2A—C1A—O1A107.79 (18)C45—C47—H47C109.5
O2A—C1A—H1AA110.1H47A—C47—H47B109.5
O2A—C1A—H1AB110.1H47A—C47—H47C109.5
H1AA—C1A—H1AB108.5H47B—C47—H47C109.5
C3A—C2A—O1A109.5 (2)C48—C47—C45165.9 (15)
C7A—C2A—O1A127.8 (2)C48—C47—H47A59.5
C7A—C2A—C3A122.7 (2)C48—C47—H47B69.5
C2A—C3A—O2A110.4 (2)C48—C47—H47C83.6
C4A—C3A—O2A127.7 (2)C40—C42A—H42C111.0
C4A—C3A—C2A122.0 (2)C40—C42A—H42D111.0
C3A—C4A—H4A121.7C40—C42A—C43A103.6 (5)
C3A—C4A—C5A116.6 (2)H42C—C42A—H42D109.0
C5A—C4A—H4A121.7C43A—C42A—H42C111.0
C4A—C5A—H5A118.9C43A—C42A—H42D111.0
C6A—C5A—C4A122.1 (2)C42A—C43A—H43C107.7
C6A—C5A—H5A118.9C42A—C43A—H43D107.7
C5A—C6A—C7A119.8 (2)H43C—C43A—H43D107.1
C5A—C6A—C8A119.9 (2)C44A—C43A—C42A118.3 (7)
C7A—C6A—C8A120.3 (2)C44A—C43A—H43C107.7
C2A—C7A—C6A116.7 (2)C44A—C43A—H43D107.7
C2A—C7A—H7AA121.6C43A—C44A—H44A112.4
C6A—C7A—H7AA121.6C45A—C44A—C43A135.1 (9)
C9A—C8A—C6A120.7 (2)C45A—C44A—H44A112.4
C9A—C8A—C12A118.3 (2)C44A—C45A—C46A123.9 (9)
C12A—C8A—C6A121.0 (2)C44A—C45A—C47A122.5 (10)
O3A—C9A—H9AA117.3C46A—C45A—C47A113.1 (9)
C8A—C9A—O3A125.4 (2)C45A—C46A—H46D109.5
C8A—C9A—H9AA117.3C45A—C46A—H46E109.5
O3A—C10A—C11A121.4 (2)C45A—C46A—H46F109.5
O3A—C10A—C17A116.95 (19)H46D—C46A—H46E109.5
C11A—C10A—C17A121.7 (2)H46D—C46A—H46F109.5
C10A—C11A—C12A120.1 (2)H46E—C46A—H46F109.5
C10A—C11A—C13A119.0 (2)C45A—C47A—H47D109.5
C13A—C11A—C12A120.9 (2)C45A—C47A—H47E109.5
O4A—C12A—C8A122.1 (2)C45A—C47A—H47F109.5
O4A—C12A—C11A121.5 (2)H47D—C47A—H47E109.5
C11A—C12A—C8A116.31 (19)H47D—C47A—H47F109.5
C11A—C13A—H13A119.6H47E—C47A—H47F109.5
C14A—C13A—C11A120.8 (2)C40—C42B—C43104.5 (5)
C14A—C13A—H13A119.6C40—C42B—H42E107.5
O5A—C14A—C13A125.7 (2)C40—C42B—H42F107.5
O5A—C14A—C16A115.2 (2)C40—C42B—C43B119.5 (6)
C13A—C14A—C16A119.1 (2)C43—C42B—H42E144.7
O5A—C15A—H15D109.5C43—C42B—H42F76.7
O5A—C15A—H15E109.5H42E—C42B—H42F107.0
O5A—C15A—H15F109.5C43B—C42B—C4341.6 (4)
H15D—C15A—H15E109.5C43B—C42B—H42E107.5
H15D—C15A—H15F109.5C43B—C42B—H42F107.5
H15E—C15A—H15F109.5C42—C43B—C44106.0 (7)
O6A—C16A—C14A116.2 (2)C42—C43B—C42B9.4 (8)
O6A—C16A—C17A122.1 (2)C42—C43B—H43E115.0
C17A—C16A—C14A121.6 (2)C42—C43B—H43F115.1
C10A—C17A—C18A124.5 (2)C43—C43B—C4269.3 (6)
C16A—C17A—C10A117.8 (2)C43—C43B—C4456.3 (5)
C16A—C17A—C18A117.6 (2)C43—C43B—C42B78.6 (7)
C17A—C18A—H18A120.4C43—C43B—H43E118.0
C19A—C18A—C17A119.2 (2)C43—C43B—H43F125.3
C19A—C18A—H18A120.4C43—C43B—C44B27.3 (4)
C18A—C19A—H19A119.2C44—C43B—H43E64.3
C18A—C19A—C20A121.6 (2)C44—C43B—H43F136.1
C20A—C19A—H19A119.2C42B—C43B—C44112.2 (7)
O6A—C20A—C19A109.59 (19)C42B—C43B—H43E110.6
O6A—C20A—C21A103.73 (19)C42B—C43B—H43F110.6
O6A—C20A—C22A107.68 (19)H43E—C43B—H43F108.7
C19A—C20A—C21A113.1 (2)C44B—C43B—C4296.3 (6)
C19A—C20A—C22A110.1 (2)C44B—C43B—C4447.6 (6)
C21A—C20A—C22A112.2 (2)C44B—C43B—C42B105.7 (7)
C20A—C21A—H21D109.5C44B—C43B—H43E110.6
C20A—C21A—H21E109.5C44B—C43B—H43F110.6
C20A—C21A—H21F109.5C43—C44B—C4488.7 (12)
H21D—C21A—H21E109.5C43—C44B—C43B54.5 (10)
H21D—C21A—H21F109.5C43—C44B—H44B66.4
H21E—C21A—H21F109.5C43—C44B—C45B169.5 (18)
C20A—C22A—H22D109.5C44—C44B—C43B77.2 (7)
C20A—C22A—H22E109.5C44—C44B—H44B94.0
C20A—C22A—H22F109.5C44—C44B—C45B98.7 (8)
H22D—C22A—H22E109.5C43B—C44B—H44B120.2
H22D—C22A—H22F109.5C45B—C44B—C43B119.7 (7)
H22E—C22A—H22F109.5C45B—C44B—H44B120.2
C23—O7—H7109.5C43—C45B—C4442.7 (2)
C33—O9—H9109.5C45—C45B—C4381.8 (3)
O7—C23—C24117.8 (2)C45—C45B—C4440.1 (2)
O7—C23—C28122.7 (2)C46—C45B—C43121.5 (6)
C24—C23—C28119.5 (2)C46—C45B—C4487.7 (5)
C23—C24—H24120.2C46—C45B—C4550.1 (4)
C25—C24—C23119.6 (2)C46—C45B—C47B46.6 (6)
C25—C24—H24120.2C44B—C45B—C433.5 (6)
C24—C25—H25118.9C44B—C45B—C4440.2 (6)
C24—C25—C26122.1 (2)C44B—C45B—C4579.7 (7)
C26—C25—H25118.9C44B—C45B—C46121.2 (8)
C25—C26—C27117.4 (2)C44B—C45B—C46B111.0 (7)
C25—C26—C29120.1 (2)C44B—C45B—C47B132.2 (8)
C27—C26—C29122.5 (2)C46B—C45B—C43113.4 (7)
C26—C27—H27119.5C46B—C45B—C44108.2 (7)
C28—C27—C26121.0 (2)C46B—C45B—C45104.7 (7)
C28—C27—H27119.5C46B—C45B—C46110.0 (7)
C23—C28—H28119.8C46B—C45B—C47B116.2 (7)
C27—C28—C23120.4 (2)C47B—C45B—C43129.4 (7)
C27—C28—H28119.8C47B—C45B—C44123.9 (8)
C26—C29—H29116.5C47B—C45B—C4594.7 (8)
C30—C29—C26127.0 (2)C45B—C46B—H46G109.5
C30—C29—H29116.5C45B—C46B—H46H109.5
C29—C30—H30118.9C45B—C46B—H46I109.5
C29—C30—C31122.1 (2)H46G—C46B—H46H109.5
C31—C30—H30118.9H46G—C46B—H46I109.5
O8—C31—C30119.2 (2)H46H—C46B—H46I109.5
O8—C31—C32120.2 (2)C46—C47B—C45B66.5 (7)
C32—C31—C30120.6 (2)C46—C47B—H47G95.1
C33—C32—C31120.2 (2)C46—C47B—H47H53.6
C37—C32—C31123.4 (2)C46—C47B—H47I154.6
C37—C32—C33116.5 (2)C45B—C47B—H47G109.5
O9—C33—C32121.3 (2)C45B—C47B—H47H109.5
O9—C33—C34116.5 (2)C45B—C47B—H47I109.5
C34—C33—C32122.2 (2)H47G—C47B—H47H109.5
C33—C34—H34120.4H47G—C47B—H47I109.5
C35—C34—C33119.1 (2)H47H—C47B—H47I109.5
C35—C34—H34120.4C48—O11—H11109.5
C34—C35—C36120.1 (2)C47—C48—O11140.1 (19)
O10—C35—C34124.7 (2)C47—C48—H48A67.5
O10—C35—C36115.1 (2)C47—C48—H48B44.0
C35—C36—H36119.9C47—C48—C49110 (2)
C37—C36—C35120.1 (2)O11—C48—H48A110.2
C37—C36—H36119.9O11—C48—H48B110.2
C35—O10—C38117.74 (18)O11—C48—C49107.4 (19)
C32—C37—H37119.0H48A—C48—H48B108.5
C36—C37—C32121.9 (2)C49—C48—H48A110.2
C36—C37—H37119.0C49—C48—H48B110.2
O10—C38—H38A110.4C48—C49—H49A109.5
O10—C38—H38B110.4C48—C49—H49B109.5
O10—C38—C39106.7 (2)C48—C49—H49C109.5
H38A—C38—H38B108.6H49A—C49—H49B109.5
C39—C38—H38A110.4H49A—C49—H49C109.5
C39—C38—H38B110.4H49B—C49—H49C109.5
O1—C2—C3—O21.6 (3)C40—C42—C43B—C4395.1 (9)
O1—C2—C3—C4175.8 (2)C40—C42—C43B—C44138.7 (8)
O1—C2—C7—C6177.7 (2)C40—C42—C43B—C42B89 (3)
O2—C3—C4—C5179.7 (2)C40—C42—C43B—C44B91.1 (10)
O3—C10—C11—C121.6 (4)C40—C42A—C43A—C44A165.2 (9)
O3—C10—C11—C13177.2 (2)C40—C42B—C43B—C4274.8 (16)
O3—C10—C17—C16179.1 (2)C40—C42B—C43B—C4378.3 (10)
O3—C10—C17—C183.4 (4)C40—C42B—C43B—C44124.4 (9)
O5—C14—C16—O60.6 (3)C40—C42B—C43B—C44B74.4 (12)
O5—C14—C16—C17176.2 (2)C41—C40—C42—C4376.7 (9)
O6—C16—C17—C10178.2 (2)C41—C40—C42—C43B24.2 (10)
O6—C16—C17—C182.2 (4)C41—C40—C42A—C43A49.9 (9)
C1—O1—C2—C317.1 (3)C41—C40—C42B—C4387.2 (7)
C1—O1—C2—C7164.2 (3)C41—C40—C42B—C43B45.0 (10)
C1—O2—C3—C214.7 (3)C42—C40—C42B—C4326 (3)
C1—O2—C3—C4168.0 (3)C42—C40—C42B—C43B68 (3)
C2—O1—C1—O226.3 (3)C42—C43—C44—C45133.7 (10)
C2—C3—C4—C52.7 (4)C42—C43—C44—C43B54.7 (8)
C3—O2—C1—O124.8 (3)C42—C43—C44—C44B158.7 (16)
C3—C2—C7—C60.7 (4)C42—C43—C44—C45B153.4 (8)
C3—C4—C5—C60.4 (4)C42—C43—C42B—C4055 (4)
C4—C5—C6—C71.6 (4)C42—C43—C42B—C43B174 (4)
C4—C5—C6—C8174.0 (2)C42—C43—C43B—C44127.3 (5)
C5—C6—C7—C21.5 (3)C42—C43—C43B—C42B0.6 (3)
C5—C6—C8—C937.0 (3)C42—C43—C43B—C44B171.2 (14)
C5—C6—C8—C12145.1 (2)C42—C43—C44B—C44100 (4)
C6—C8—C9—O3178.3 (2)C42—C43—C44B—C43B25 (4)
C6—C8—C12—O41.4 (4)C42—C43—C44B—C45B34 (11)
C6—C8—C12—C11178.7 (2)C42—C43B—C44B—C438.2 (13)
C7—C2—C3—O2179.7 (2)C42—C43B—C44B—C44105.9 (7)
C7—C2—C3—C42.9 (4)C42—C43B—C44B—C45B161.3 (10)
C7—C6—C8—C9138.6 (2)C43—C42—C43B—C4443.6 (4)
C7—C6—C8—C1239.3 (3)C43—C42—C43B—C42B176 (2)
C8—C6—C7—C2174.2 (2)C43—C42—C43B—C44B4.0 (7)
C9—O3—C10—C111.7 (3)C43—C44—C45—C462.9 (15)
C9—O3—C10—C17179.2 (2)C43—C44—C45—C47179.8 (9)
C9—C8—C12—O4176.4 (2)C43—C44—C45—C45B20.3 (10)
C9—C8—C12—C113.5 (3)C43—C44—C43B—C4250.7 (5)
C10—O3—C9—C81.1 (4)C43—C44—C43B—C42B58.1 (7)
C10—C11—C12—O4178.9 (2)C43—C44—C43B—C44B33.2 (7)
C10—C11—C12—C81.0 (3)C43—C44—C44B—C43B53.8 (11)
C10—C11—C13—C140.9 (4)C43—C44—C44B—C45B172.4 (15)
C10—C17—C18—C19174.1 (3)C43—C42B—C43B—C424 (2)
C11—C10—C17—C160.0 (4)C43—C42B—C43B—C4446.1 (5)
C11—C10—C17—C18175.7 (2)C43—C42B—C43B—C44B3.9 (7)
C11—C13—C14—O5178.1 (2)C43—C43B—C44B—C4497.6 (14)
C11—C13—C14—C161.7 (4)C43—C43B—C44B—C45B170 (2)
C12—C8—C9—O33.7 (4)C43—C44B—C45B—C44134 (8)
C12—C11—C13—C14179.7 (2)C43—C44B—C45B—C45126 (8)
C13—C11—C12—O40.1 (4)C43—C44B—C45B—C4696 (8)
C13—C11—C12—C8179.7 (2)C43—C44B—C45B—C46B133 (8)
C13—C14—C16—O6179.3 (2)C43—C44B—C45B—C47B38 (8)
C13—C14—C16—C173.7 (4)C43—C45B—C47B—C4698.8 (10)
C14—C16—C17—C102.8 (4)C44—C43—C42B—C40179.3 (6)
C14—C16—C17—C18173.2 (2)C44—C43—C42B—C43B61.0 (8)
C15—O5—C14—C134.1 (4)C44—C43—C43B—C42127.3 (5)
C15—O5—C14—C16175.8 (2)C44—C43—C43B—C42B126.7 (5)
C16—O6—C20—C1933.5 (3)C44—C43—C43B—C44B61.5 (12)
C16—O6—C20—C21154.8 (2)C44—C43—C44B—C43B75.2 (10)
C16—O6—C20—C2286.1 (3)C44—C43—C44B—C45B134 (8)
C16—C17—C18—C1910.2 (4)C44—C45—C46—C45B28.9 (9)
C17—C10—C11—C12179.4 (2)C44—C45—C46—C47B0.5 (19)
C17—C10—C11—C131.9 (4)C44—C45—C47—C48127 (6)
C17—C18—C19—C205.4 (4)C44—C45—C45B—C4311.2 (6)
C18—C19—C20—O626.2 (4)C44—C45—C45B—C46155.1 (8)
C18—C19—C20—C21142.3 (3)C44—C45—C45B—C44B8.3 (7)
C18—C19—C20—C2292.5 (3)C44—C45—C45B—C46B101.0 (8)
C20—O6—C16—C14163.3 (2)C44—C45—C45B—C47B140.4 (7)
C20—O6—C16—C1721.1 (4)C44—C43B—C44B—C4397.6 (14)
O1A—C2A—C3A—O2A0.3 (3)C44—C43B—C44B—C45B92.8 (11)
O1A—C2A—C3A—C4A179.7 (2)C44—C44B—C45B—C43134 (8)
O1A—C2A—C7A—C6A178.9 (2)C44—C44B—C45B—C458.3 (7)
O2A—C3A—C4A—C5A179.3 (2)C44—C44B—C45B—C4637.7 (10)
O3A—C10A—C11A—C12A1.4 (4)C44—C44B—C45B—C46B93.7 (9)
O3A—C10A—C11A—C13A178.4 (2)C44—C44B—C45B—C47B95.3 (14)
O3A—C10A—C17A—C16A178.5 (2)C44—C45B—C47B—C4645.3 (9)
O3A—C10A—C17A—C18A6.6 (3)C45—C44—C43B—C42177.2 (6)
O5A—C14A—C16A—O6A1.8 (3)C45—C44—C43B—C43126.5 (7)
O5A—C14A—C16A—C17A177.3 (2)C45—C44—C43B—C42B175.4 (7)
O6A—C16A—C17A—C10A179.3 (2)C45—C44—C43B—C44B93.3 (7)
O6A—C16A—C17A—C18A4.0 (4)C45—C44—C44B—C43160.6 (13)
C1A—O1A—C2A—C3A8.7 (3)C45—C44—C44B—C43B106.8 (8)
C1A—O1A—C2A—C7A172.2 (3)C45—C44—C44B—C45B11.9 (9)
C1A—O2A—C3A—C2A9.3 (3)C45—C46—C45B—C4343.2 (7)
C1A—O2A—C3A—C4A171.3 (3)C45—C46—C45B—C4415.8 (5)
C2A—O1A—C1A—O2A14.4 (3)C45—C46—C45B—C44B39.0 (9)
C2A—C3A—C4A—C5A1.4 (4)C45—C46—C45B—C46B92.8 (8)
C3A—O2A—C1A—O1A14.6 (3)C45—C46—C45B—C47B159.6 (9)
C3A—C2A—C7A—C6A2.1 (4)C45—C46—C47B—C45B31.4 (13)
C3A—C4A—C5A—C6A1.8 (4)C45—C47—C48—O1194 (7)
C4A—C5A—C6A—C7A0.4 (4)C45—C47—C48—C49106 (6)
C4A—C5A—C6A—C8A178.8 (2)C45—C45B—C47B—C4615.6 (7)
C5A—C6A—C7A—C2A1.6 (4)C46—C45—C47—C4855 (7)
C5A—C6A—C8A—C9A39.7 (4)C46—C45—C45B—C43143.9 (6)
C5A—C6A—C8A—C12A137.8 (2)C46—C45—C45B—C44155.1 (8)
C6A—C8A—C9A—O3A175.7 (2)C46—C45—C45B—C44B146.8 (7)
C6A—C8A—C12A—O4A2.9 (4)C46—C45—C45B—C46B104.0 (8)
C6A—C8A—C12A—C11A175.8 (2)C46—C45—C45B—C47B14.7 (6)
C7A—C2A—C3A—O2A178.8 (2)C47—C45—C46—C45B153.7 (9)
C7A—C2A—C3A—C4A0.6 (4)C47—C45—C46—C47B176.9 (13)
C7A—C6A—C8A—C9A141.9 (3)C47—C45—C45B—C43149.8 (18)
C7A—C6A—C8A—C12A40.6 (3)C47—C45—C45B—C44139 (2)
C8A—C6A—C7A—C2A176.9 (2)C47—C45—C45B—C4666.3 (19)
C9A—O3A—C10A—C11A1.4 (3)C47—C45—C45B—C44B146.9 (19)
C9A—O3A—C10A—C17A178.6 (2)C47—C45—C45B—C46B38 (2)
C9A—C8A—C12A—O4A179.5 (2)C47—C45—C45B—C47B81 (2)
C9A—C8A—C12A—C11A1.8 (3)C42A—C43A—C44A—C45A113 (2)
C10A—O3A—C9A—C8A0.3 (4)C43A—C44A—C45A—C46A13 (3)
C10A—C11A—C12A—O4A178.9 (2)C43A—C44A—C45A—C47A175 (2)
C10A—C11A—C12A—C8A0.2 (3)C42B—C40—C42—C43147 (4)
C10A—C11A—C13A—C14A2.2 (4)C42B—C40—C42—C43B95 (4)
C10A—C17A—C18A—C19A171.8 (2)C42B—C43—C44—C45129.0 (10)
C11A—C10A—C17A—C16A1.6 (4)C42B—C43—C44—C43B50.0 (6)
C11A—C10A—C17A—C18A173.4 (2)C42B—C43—C44—C44B154.1 (16)
C11A—C13A—C14A—O5A179.4 (2)C42B—C43—C44—C45B148.7 (7)
C11A—C13A—C14A—C16A0.2 (4)C42B—C43—C43B—C420.6 (3)
C12A—C8A—C9A—O3A1.9 (4)C42B—C43—C43B—C44126.7 (5)
C12A—C11A—C13A—C14A178.0 (2)C42B—C43—C43B—C44B171.9 (14)
C13A—C11A—C12A—O4A1.2 (4)C42B—C43—C44B—C4493 (3)
C13A—C11A—C12A—C8A179.9 (2)C42B—C43—C44B—C43B18 (3)
C13A—C14A—C16A—O6A178.9 (2)C42B—C43—C44B—C45B41 (10)
C13A—C14A—C16A—C17A3.4 (4)C42B—C43B—C44B—C438.3 (14)
C14A—C16A—C17A—C10A4.0 (4)C42B—C43B—C44B—C44105.9 (8)
C14A—C16A—C17A—C18A171.2 (2)C42B—C43B—C44B—C45B161.3 (9)
C15A—O5A—C14A—C13A5.9 (3)C43B—C42—C43—C4462.8 (8)
C15A—O5A—C14A—C16A174.9 (2)C43B—C42—C43—C42B6 (4)
C16A—O6A—C20A—C19A39.2 (3)C43B—C42—C43—C44B28 (4)
C16A—O6A—C20A—C21A160.2 (2)C43B—C42—C43—C45B36.9 (12)
C16A—O6A—C20A—C22A80.6 (2)C43B—C43—C44—C4579.0 (10)
C16A—C17A—C18A—C19A13.3 (4)C43B—C43—C44—C44B104.0 (14)
C17A—C10A—C11A—C12A178.6 (2)C43B—C43—C44—C45B98.7 (6)
C17A—C10A—C11A—C13A1.5 (4)C43B—C43—C42B—C40118.3 (9)
C17A—C18A—C19A—C20A5.6 (4)C43B—C43—C44B—C4475.2 (10)
C18A—C19A—C20A—O6A30.6 (3)C43B—C43—C44B—C45B59 (8)
C18A—C19A—C20A—C21A145.8 (2)C43B—C44—C45—C4643.4 (11)
C18A—C19A—C20A—C22A87.7 (3)C43B—C44—C45—C47133.8 (9)
C20A—O6A—C16A—C14A160.6 (2)C43B—C44—C45—C45B66.7 (6)
C20A—O6A—C16A—C17A24.0 (3)C43B—C44—C44B—C4353.8 (11)
O7—C23—C24—C25179.8 (2)C43B—C44—C44B—C45B118.6 (7)
O7—C23—C28—C27179.5 (2)C43B—C44B—C45B—C4354 (7)
O8—C31—C32—C331.1 (4)C43B—C44B—C45B—C4480.2 (10)
O8—C31—C32—C37179.1 (2)C43B—C44B—C45B—C4571.9 (10)
O9—C33—C34—C35179.7 (2)C43B—C44B—C45B—C4642.5 (15)
C23—C24—C25—C260.5 (4)C43B—C44B—C45B—C46B173.8 (9)
C24—C23—C28—C270.7 (4)C43B—C44B—C45B—C47B15.2 (19)
C24—C25—C26—C271.1 (4)C44B—C43—C44—C4525.1 (16)
C24—C25—C26—C29177.2 (2)C44B—C43—C44—C43B104.0 (14)
C25—C26—C27—C280.8 (4)C44B—C43—C44—C45B5.4 (11)
C25—C26—C29—C30178.9 (2)C44B—C43—C42B—C4098 (3)
C26—C27—C28—C230.1 (4)C44B—C43—C42B—C43B21 (3)
C26—C29—C30—C31176.9 (2)C44B—C43—C43B—C42171.2 (14)
C27—C26—C29—C302.8 (4)C44B—C43—C43B—C4461.5 (12)
C28—C23—C24—C250.4 (4)C44B—C43—C43B—C42B171.9 (14)
C29—C26—C27—C28177.5 (2)C44B—C44—C45—C4614.6 (12)
C29—C30—C31—O81.4 (4)C44B—C44—C45—C47168.1 (9)
C29—C30—C31—C32179.2 (2)C44B—C44—C45—C45B8.6 (7)
C30—C31—C32—C33178.3 (2)C44B—C44—C43B—C4283.9 (6)
C30—C31—C32—C371.5 (4)C44B—C44—C43B—C4333.2 (7)
C31—C32—C33—O90.7 (4)C44B—C44—C43B—C42B91.3 (7)
C31—C32—C33—C34179.9 (2)C44B—C45B—C47B—C4696.0 (13)
C31—C32—C37—C36179.7 (2)C45B—C43—C44—C4519.7 (9)
C32—C33—C34—C350.4 (4)C45B—C43—C44—C43B98.7 (6)
C33—C32—C37—C360.0 (4)C45B—C43—C44—C44B5.4 (11)
C33—C34—C35—C361.4 (4)C45B—C43—C42B—C4088.0 (11)
C33—C34—C35—O10177.9 (2)C45B—C43—C42B—C43B30.3 (10)
C34—C35—C36—C371.7 (4)C45B—C43—C43B—C42165.2 (5)
C34—C35—O10—C384.9 (3)C45B—C43—C43B—C4467.5 (4)
C35—C36—C37—C321.0 (4)C45B—C43—C43B—C42B165.8 (5)
C35—O10—C38—C39178.4 (2)C45B—C43—C43B—C44B6.0 (12)
C36—C35—O10—C38174.3 (2)C45B—C43—C44B—C44134 (8)
O10—C35—C36—C37177.6 (2)C45B—C43—C44B—C43B59 (8)
O10—C38—C39—C40115.4 (3)C45B—C44—C45—C4623.3 (7)
C37—C32—C33—O9179.0 (2)C45B—C44—C45—C47159.5 (11)
C37—C32—C33—C340.3 (4)C45B—C44—C43B—C42119.8 (6)
C38—C39—C40—C410.1 (4)C45B—C44—C43B—C4369.1 (6)
C38—C39—C40—C42172.5 (4)C45B—C44—C43B—C42B127.2 (6)
C38—C39—C40—C42A177.2 (5)C45B—C44—C43B—C44B35.9 (4)
C38—C39—C40—C42B177.2 (5)C45B—C44—C44B—C43172.4 (15)
C39—C40—C42—C4396.3 (8)C45B—C44—C44B—C43B118.6 (7)
C39—C40—C42—C43B148.8 (8)C45B—C45—C46—C47B29.4 (12)
C39—C40—C42A—C43A132.5 (7)C45B—C45—C47—C483 (8)
C39—C40—C42B—C4395.2 (5)C46B—C45B—C47B—C4693.4 (10)
C39—C40—C42B—C43B137.4 (7)C47B—C46—C45B—C43116.5 (9)
C40—C42—C43—C44174.8 (7)C47B—C46—C45B—C44143.8 (8)
C40—C42—C43—C42B118 (5)C47B—C46—C45B—C45159.6 (9)
C40—C42—C43—C43B112.0 (10)C47B—C46—C45B—C44B120.6 (10)
C40—C42—C43—C44B84 (4)C47B—C46—C45B—C46B107.6 (9)
C40—C42—C43—C45B75.1 (15)
Full assignment of unknown species (X) that was later established as (II) (see Fig. 1) top
Label1H (ppm)13C (ppm)Predicted 13C (ppm)
14.5967.365.4
25.48118.5119.6
3-142.3142.8
41.7516.816.7
52.0939.539.6
62.1326.326.3
75.09123.6123.8
8-132.0132.2
91.6825.825.8
101.6117.717.7
11-165.6165.3
126.48101.7101.6
1313.55 (OH)166.6166.6
14-114.0114.0
157.82131.1131.1
166.49108.2111.0
17-191.8191.7
187.45117.8117.5
197.84144.2145.9
20-127.4127.6
217.55130.5130.5
226.88116.0116.1
23-158.4158.4
Ions in positive ion mode; M = (I). top
IonCalculatedMeasuredDifference
[M + H]+379.1176379.11700.0006
[2M + Na]+779.2099779.20890.0010
[3M + Na]+1157.32021157.32070.0005
Ions in negative ion mode; M = (II). top
IonCalculatedMeasuredDifference
[M - H]-391.2279391.19180.0361
[M - C10H17]-254.0948254.05870.0361
[M - C9H8O2]-148.0530148.01680.0362
 

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