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Annona­lide (3β,20-ep­oxy-3α,16-dihy­droxy-15-oxo-7-pimaren-19,6β-olide, C20H26O6, 1) is the major (9βH)-pimarane diterpene isolated from tubers of Cassimirella ampla, and it exhibits cytotoxic properties upon inter­action with ctDNA. We have prepared new derivatives of 1 by modification of the (9βH)-pimarane backbone and report here the semisynthesis and absolute configuration of a novel rearranged 19,20-δ-lactone (9βH)-pimarane. Our approach was the reduction of the carbonyl groups of 1 with sodium borohydride, at positions C15 (no stereoselectivity) and C3 (stereoselective reduction), followed by rearrangement of the 6,19-γ-lactone ring into the six-membered 19,20-δ-lactone ring in 4a (3β,6β,16-trihy­droxy-7-pimaren-19,20β-olide monohydrate, C20H30O6·H2O). The absolute structure of the new compound, 4a, was determined unambiguously with a Flack parameter x of −0.01 (11), supporting the stereochemistry assignment of 1 redetermined here. Besides the changes in the pattern of covalent bonds caused by reduction and lactone rearrangement, the conformation of one of the three fused cyclohexane rings is profoundly different in 4a, adopting a chair conformation instead of the boat shape found in 1. Further­more, the intra­molecular hydrogen bond present in 1 is lost in new compound 4a, due to hydrogen bonding between the 3-OH group and the solvent water mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618009452/qs3074sup1.cif
Contains datablocks global, compound_1, compound_4a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618009452/qs3074compound_1sup2.hkl
Contains datablock compound_1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618009452/qs3074compound_4asup3.hkl
Contains datablock compound_4a

CCDC references: 1852916; 1544714

Computing details top

For both structures, data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

13-Hydroxy-5-(2-hydroxyacetyl)-5,12-dimethyl-10,14-dioxapentacyclo[11.2.2.1{1,9}.0{2,7}.0{12,18}]octadec-7-en-11-one (compound_1) top
Crystal data top
C20H26O6Dx = 1.354 Mg m3
Mr = 362.41Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 2644 reflections
a = 6.6712 (3) Åθ = 2.5–21.5°
b = 11.9999 (5) ŵ = 0.10 mm1
c = 22.2073 (8) ÅT = 296 K
V = 1777.78 (13) Å3Needle, colourless
Z = 40.28 × 0.11 × 0.08 mm
F(000) = 776
Data collection top
Bruker APEXII CCD
diffractometer
2363 reflections with I > 2σ(I)
CCD scansRint = 0.054
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
θmax = 25.1°, θmin = 1.9°
Tmin = 0.601, Tmax = 0.992h = 77
8148 measured reflectionsk = 914
3080 independent reflectionsl = 2625
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.061 w = 1/[σ2(Fo2) + (0.081P)2 + 0.4497P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.164(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.31 e Å3
3080 reflectionsΔρmin = 0.27 e Å3
237 parametersAbsolute structure: Flack x determined using 791 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 0.1 (10)
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*/Ueq
O60.1966 (5)0.2471 (3)0.20866 (14)0.0517 (9)
O20.2503 (5)0.1843 (3)0.06324 (14)0.0513 (9)
O50.4147 (6)0.3351 (3)0.09337 (17)0.0647 (11)
O10.1766 (6)0.4353 (3)0.19939 (16)0.0635 (11)
H10.29060.43350.18560.095*
O30.4005 (15)0.3499 (4)0.0574 (2)0.149 (3)
C30.0773 (8)0.3367 (4)0.1850 (2)0.0494 (12)
C40.0581 (8)0.3164 (4)0.1166 (2)0.0441 (11)
C50.0713 (7)0.2112 (4)0.10705 (19)0.0394 (10)
H50.2030.2330.09140.047*
C100.0980 (7)0.1499 (4)0.16722 (18)0.0369 (10)
C90.1759 (7)0.0310 (4)0.15811 (19)0.0398 (11)
H90.13920.01070.19440.048*
C110.4035 (8)0.0199 (4)0.1515 (2)0.0516 (13)
H11A0.46920.05430.18570.062*
H11B0.4470.05830.11530.062*
C120.4642 (8)0.1038 (4)0.1477 (3)0.0553 (13)
H12A0.43330.13980.18570.066*
H12B0.60790.10870.14150.066*
C130.3566 (8)0.1671 (4)0.0962 (2)0.0492 (12)
C150.3988 (8)0.2915 (4)0.1001 (2)0.0526 (13)
C200.1061 (7)0.1397 (4)0.1984 (2)0.0471 (12)
H20A0.19480.0950.17360.057*
H20B0.08920.10180.23660.057*
C190.2590 (9)0.2832 (4)0.09157 (19)0.0457 (12)
C60.0413 (8)0.1463 (4)0.0591 (2)0.0464 (12)
H60.0110.1690.01970.056*
C70.0250 (8)0.0234 (4)0.0634 (2)0.0498 (13)
H70.09060.01960.03460.06*
C80.0779 (7)0.0284 (4)0.1059 (2)0.0429 (11)
C140.1268 (7)0.1511 (4)0.1033 (2)0.0487 (12)
H14A0.0580.1850.06950.058*
H14B0.08140.18730.13990.058*
C170.4241 (11)0.1258 (5)0.0348 (3)0.0730 (18)
H18A0.39850.04730.03160.11*
H18B0.5650.13950.030.11*
H18C0.35140.16470.00390.11*
C180.0168 (11)0.4178 (4)0.0818 (2)0.0650 (16)
H18D0.14510.44010.09730.097*
H18E0.02930.39930.03990.097*
H18F0.07690.4780.08640.097*
C10.2258 (8)0.2228 (4)0.2076 (2)0.0495 (12)
H1A0.35750.23250.18990.059*
H1B0.24220.18740.24660.059*
C20.1248 (8)0.3368 (4)0.2155 (2)0.0549 (14)
H2A0.10830.35280.25810.066*
H2B0.20860.39450.19810.066*
C160.4381 (17)0.3474 (5)0.1564 (3)0.112 (3)
H16A0.5580.3150.17390.134*
H16B0.3280.33120.18360.134*
O40.4632 (8)0.4609 (3)0.1547 (2)0.0832 (14)
H40.5030.47930.12120.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O60.053 (2)0.065 (2)0.0366 (18)0.0094 (18)0.0081 (16)0.0049 (16)
O20.053 (2)0.061 (2)0.0407 (18)0.0075 (19)0.0149 (16)0.0080 (15)
O50.058 (2)0.079 (2)0.057 (2)0.019 (2)0.0135 (19)0.011 (2)
O10.078 (3)0.066 (2)0.046 (2)0.025 (2)0.0127 (19)0.0160 (17)
O30.311 (10)0.076 (3)0.060 (3)0.036 (5)0.001 (5)0.016 (2)
C30.055 (3)0.055 (3)0.038 (3)0.006 (3)0.002 (2)0.006 (2)
C40.050 (3)0.049 (2)0.034 (2)0.001 (2)0.003 (2)0.000 (2)
C50.040 (3)0.049 (2)0.029 (2)0.004 (2)0.004 (2)0.0006 (19)
C100.038 (2)0.047 (2)0.026 (2)0.004 (2)0.0012 (19)0.0018 (18)
C90.040 (3)0.047 (2)0.032 (2)0.004 (2)0.002 (2)0.000 (2)
C110.040 (3)0.054 (3)0.061 (3)0.007 (2)0.006 (3)0.008 (3)
C120.044 (3)0.053 (3)0.068 (3)0.005 (3)0.010 (3)0.009 (3)
C130.052 (3)0.052 (3)0.044 (3)0.006 (3)0.006 (2)0.004 (2)
C150.053 (3)0.056 (3)0.049 (3)0.002 (3)0.001 (3)0.010 (2)
C200.045 (3)0.062 (3)0.034 (2)0.001 (3)0.005 (2)0.003 (2)
C190.054 (3)0.056 (3)0.027 (2)0.001 (3)0.006 (2)0.004 (2)
C60.055 (3)0.056 (3)0.028 (2)0.007 (3)0.004 (2)0.003 (2)
C70.055 (3)0.058 (3)0.037 (2)0.002 (3)0.013 (2)0.015 (2)
C80.037 (3)0.051 (3)0.040 (2)0.009 (2)0.002 (2)0.007 (2)
C140.048 (3)0.047 (3)0.051 (3)0.008 (3)0.006 (2)0.004 (2)
C170.091 (5)0.073 (4)0.055 (3)0.006 (4)0.024 (3)0.006 (3)
C180.093 (5)0.052 (3)0.050 (3)0.009 (3)0.000 (3)0.014 (3)
C10.054 (3)0.052 (3)0.042 (3)0.001 (3)0.013 (2)0.005 (2)
C20.065 (4)0.058 (3)0.042 (3)0.002 (3)0.012 (2)0.014 (2)
C160.214 (10)0.063 (4)0.058 (4)0.047 (5)0.024 (5)0.004 (3)
O40.102 (4)0.060 (2)0.087 (3)0.016 (3)0.017 (3)0.001 (2)
Geometric parameters (Å, º) top
O6—C31.437 (6)C13—C171.520 (7)
O6—C201.442 (6)C13—C151.521 (7)
O2—C191.345 (6)C13—C141.553 (7)
O2—C61.469 (6)C15—C161.443 (8)
O5—C191.212 (6)C20—H20A0.97
O1—C31.394 (6)C20—H20B0.97
O1—H10.82C6—C71.482 (7)
O3—C151.180 (6)C6—H60.98
C3—C21.509 (7)C7—C81.322 (7)
C3—C41.544 (6)C7—H70.93
C4—C191.504 (7)C8—C141.509 (6)
C4—C181.525 (7)C14—H14A0.97
C4—C51.544 (7)C14—H14B0.97
C5—C61.518 (6)C17—H18A0.96
C5—C101.536 (6)C17—H18B0.96
C5—H50.98C17—H18C0.96
C10—C11.516 (6)C18—H18D0.96
C10—C91.531 (6)C18—H18E0.96
C10—C201.532 (6)C18—H18F0.96
C9—C81.510 (6)C1—C21.535 (7)
C9—C111.532 (7)C1—H1A0.97
C9—H90.98C1—H1B0.97
C11—C121.541 (7)C2—H2A0.97
C11—H11A0.97C2—H2B0.97
C11—H11B0.97C16—O41.373 (7)
C12—C131.548 (7)C16—H16A0.97
C12—H12A0.97C16—H16B0.97
C12—H12B0.97O4—H40.82
C3—O6—C20112.2 (3)C10—C20—H20A109.2
C19—O2—C6110.1 (4)O6—C20—H20B109.2
C3—O1—H1109.5C10—C20—H20B109.2
O1—C3—O6106.7 (4)H20A—C20—H20B107.9
O1—C3—C2108.7 (4)O5—C19—O2120.4 (5)
O6—C3—C2109.4 (4)O5—C19—C4128.0 (4)
O1—C3—C4113.5 (4)O2—C19—C4111.6 (4)
O6—C3—C4106.8 (4)O2—C6—C7112.0 (4)
C2—C3—C4111.6 (4)O2—C6—C5105.5 (4)
C19—C4—C18108.5 (4)C7—C6—C5115.5 (4)
C19—C4—C5103.4 (4)O2—C6—H6107.9
C18—C4—C5113.6 (4)C7—C6—H6107.9
C19—C4—C3109.3 (4)C5—C6—H6107.9
C18—C4—C3113.6 (4)C8—C7—C6123.4 (4)
C5—C4—C3108.0 (4)C8—C7—H7118.3
C6—C5—C10114.9 (4)C6—C7—H7118.3
C6—C5—C4103.8 (4)C7—C8—C14122.9 (4)
C10—C5—C4109.7 (3)C7—C8—C9123.5 (4)
C6—C5—H5109.4C14—C8—C9113.4 (4)
C10—C5—H5109.4C8—C14—C13109.8 (4)
C4—C5—H5109.4C8—C14—H14A109.7
C1—C10—C9115.1 (4)C13—C14—H14A109.7
C1—C10—C20106.2 (4)C8—C14—H14B109.7
C9—C10—C20106.7 (4)C13—C14—H14B109.7
C1—C10—C5107.6 (4)H14A—C14—H14B108.2
C9—C10—C5111.8 (3)C13—C17—H18A109.5
C20—C10—C5109.2 (4)C13—C17—H18B109.5
C8—C9—C10113.2 (4)H18A—C17—H18B109.5
C8—C9—C11108.3 (4)C13—C17—H18C109.5
C10—C9—C11115.5 (4)H18A—C17—H18C109.5
C8—C9—H9106.4H18B—C17—H18C109.5
C10—C9—H9106.4C4—C18—H18D109.5
C11—C9—H9106.4C4—C18—H18E109.5
C9—C11—C12110.5 (4)H18D—C18—H18E109.5
C9—C11—H11A109.6C4—C18—H18F109.5
C12—C11—H11A109.6H18D—C18—H18F109.5
C9—C11—H11B109.6H18E—C18—H18F109.5
C12—C11—H11B109.6C10—C1—C2109.6 (4)
H11A—C11—H11B108.1C10—C1—H1A109.8
C11—C12—C13113.0 (4)C2—C1—H1A109.8
C11—C12—H12A109C10—C1—H1B109.8
C13—C12—H12A109C2—C1—H1B109.8
C11—C12—H12B109H1A—C1—H1B108.2
C13—C12—H12B109C3—C2—C1109.9 (4)
H12A—C12—H12B107.8C3—C2—H2A109.7
C17—C13—C15108.4 (4)C1—C2—H2A109.7
C17—C13—C12111.4 (5)C3—C2—H2B109.7
C15—C13—C12110.7 (4)C1—C2—H2B109.7
C17—C13—C14110.0 (5)H2A—C2—H2B108.2
C15—C13—C14107.4 (4)O4—C16—C15117.3 (5)
C12—C13—C14108.8 (4)O4—C16—H16A108
O3—C15—C16114.8 (5)C15—C16—H16A108
O3—C15—C13122.6 (5)O4—C16—H16B108
C16—C15—C13122.6 (5)C15—C16—H16B108
O6—C20—C10111.9 (4)H16A—C16—H16B107.2
O6—C20—H20A109.2C16—O4—H4109.5
C20—O6—C3—O1178.1 (4)C14—C13—C15—C1689.2 (8)
C20—O6—C3—C260.7 (5)C3—O6—C20—C102.4 (5)
C20—O6—C3—C460.2 (5)C1—C10—C20—O657.5 (5)
O1—C3—C4—C1973.5 (5)C9—C10—C20—O6179.2 (4)
O6—C3—C4—C1943.8 (5)C5—C10—C20—O658.2 (5)
C2—C3—C4—C19163.3 (4)C6—O2—C19—O5171.3 (4)
O1—C3—C4—C1847.8 (7)C6—O2—C19—C47.0 (5)
O6—C3—C4—C18165.0 (4)C18—C4—C19—O565.7 (7)
C2—C3—C4—C1875.5 (6)C5—C4—C19—O5173.4 (5)
O1—C3—C4—C5174.7 (4)C3—C4—C19—O558.6 (6)
O6—C3—C4—C568.0 (5)C18—C4—C19—O2112.5 (5)
C2—C3—C4—C551.4 (5)C5—C4—C19—O28.4 (5)
C19—C4—C5—C619.5 (5)C3—C4—C19—O2123.2 (4)
C18—C4—C5—C697.8 (5)C19—O2—C6—C7146.2 (4)
C3—C4—C5—C6135.3 (4)C19—O2—C6—C519.8 (5)
C19—C4—C5—C10103.8 (4)C10—C5—C6—O296.0 (4)
C18—C4—C5—C10138.9 (4)C4—C5—C6—O223.8 (5)
C3—C4—C5—C1012.0 (5)C10—C5—C6—C728.1 (6)
C6—C5—C10—C1175.8 (4)C4—C5—C6—C7148.0 (4)
C4—C5—C10—C167.7 (5)O2—C6—C7—C8120.1 (5)
C6—C5—C10—C948.5 (5)C5—C6—C7—C80.7 (8)
C4—C5—C10—C9165.0 (4)C6—C7—C8—C14167.9 (5)
C6—C5—C10—C2069.3 (5)C6—C7—C8—C95.5 (8)
C4—C5—C10—C2047.2 (5)C10—C9—C8—C716.1 (7)
C1—C10—C9—C8164.9 (4)C11—C9—C8—C7113.3 (6)
C20—C10—C9—C877.6 (4)C10—C9—C8—C14169.9 (4)
C5—C10—C9—C841.6 (5)C11—C9—C8—C1460.6 (5)
C1—C10—C9—C1139.2 (6)C7—C8—C14—C13113.5 (5)
C20—C10—C9—C11156.7 (4)C9—C8—C14—C1360.5 (5)
C5—C10—C9—C1184.1 (5)C17—C13—C14—C867.7 (5)
C8—C9—C11—C1256.3 (6)C15—C13—C14—C8174.5 (4)
C10—C9—C11—C12175.5 (4)C12—C13—C14—C854.6 (5)
C9—C11—C12—C1355.9 (6)C9—C10—C1—C2176.9 (4)
C11—C12—C13—C1767.4 (6)C20—C10—C1—C259.1 (5)
C11—C12—C13—C15171.9 (4)C5—C10—C1—C257.7 (5)
C11—C12—C13—C1454.1 (6)O1—C3—C2—C1172.3 (4)
C17—C13—C15—O328.6 (9)O6—C3—C2—C156.2 (5)
C12—C13—C15—O3151.1 (7)C4—C3—C2—C161.7 (6)
C14—C13—C15—O390.2 (8)C10—C1—C2—C34.7 (6)
C17—C13—C15—C16152.0 (7)O3—C15—C16—O43.0 (13)
C12—C13—C15—C1629.5 (9)C13—C15—C16—O4176.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O50.822.53.084 (5)129
O1—H1···O4i0.822.192.883 (6)143
O4—H4···O5ii0.822.382.917 (6)124
Symmetry codes: (i) x1, y+1, z; (ii) x+1, y1, z.
5-(1,2-Dihydroxyethyl]-9,17-dihydroxy-5,11-dimethyl-13-\ oxatetracyclo[9.3.3.01,10.02,7]heptadec-7-en-12-one monohydrate (compound_4a) top
Crystal data top
C20H30O6·H2ODx = 1.336 Mg m3
Mr = 384.45Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P21212Cell parameters from 3033 reflections
a = 11.7555 (14) Åθ = 4.4–67.6°
b = 20.224 (2) ŵ = 0.83 mm1
c = 8.0385 (11) ÅT = 296 K
V = 1911.1 (4) Å3Prism, colourless
Z = 40.32 × 0.15 × 0.10 mm
F(000) = 832
Data collection top
Bruker APEXII CCD
diffractometer
2594 reflections with I > 2σ(I)
CCD scansRint = 0.045
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
θmax = 68.2°, θmin = 4.4°
Tmin = 0.737, Tmax = 0.921h = 1313
9565 measured reflectionsk = 2323
3311 independent reflectionsl = 96
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.046 w = 1/[σ2(Fo2) + (0.0845P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.137(Δ/σ)max = 0.002
S = 1.05Δρmax = 0.22 e Å3
3311 reflectionsΔρmin = 0.24 e Å3
250 parametersAbsolute structure: Flack x determined using 917 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 0.01 (11)
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*/Ueq
O40.5239 (3)0.1565 (2)0.5057 (4)0.0830 (11)
H40.55790.13330.43850.125*
O1W0.3841 (3)0.08743 (18)1.1393 (5)0.0773 (11)
H1W0.457 (5)0.102 (3)1.106 (8)0.116*
H2W0.347 (5)0.116 (3)1.193 (9)0.116*
O60.2595 (2)0.21115 (12)1.0532 (4)0.0535 (7)
O30.3079 (2)0.18204 (13)0.3655 (3)0.0500 (7)
H30.28650.22030.35380.075*
O20.2769 (2)0.18946 (12)0.6913 (3)0.0482 (7)
H20.33080.18120.62990.072*
O10.3591 (3)0.04459 (16)1.2152 (4)0.0699 (9)
H10.37790.00571.20650.105*
O50.4318 (3)0.17254 (14)1.0392 (5)0.0751 (10)
C160.4223 (3)0.1240 (3)0.5568 (6)0.0703 (14)
H16A0.41150.08460.48990.084*
H16B0.43000.11030.67200.084*
C150.3202 (3)0.1676 (2)0.5399 (5)0.0479 (9)
H150.33570.20910.59850.058*
C130.2090 (3)0.13804 (18)0.6106 (4)0.0398 (8)
C140.1143 (3)0.19067 (17)0.5975 (4)0.0416 (9)
H14A0.09690.19840.48110.050*
H14B0.14140.23190.64460.050*
C80.0079 (3)0.16978 (16)0.6866 (4)0.0371 (8)
C70.0887 (3)0.15998 (17)0.6081 (4)0.0415 (8)
H70.09040.16920.49480.050*
C60.1959 (3)0.13531 (17)0.6852 (4)0.0396 (8)
H60.22720.10060.61350.048*
C50.1751 (3)0.10561 (16)0.8587 (4)0.0357 (8)
H50.14300.06140.84120.043*
C40.2861 (3)0.09611 (17)0.9583 (4)0.0401 (8)
C190.3321 (4)0.16216 (18)1.0137 (5)0.0506 (10)
C200.1410 (3)0.21167 (18)1.0025 (5)0.0449 (9)
H20A0.13400.23900.90390.054*
H20B0.09670.23241.08990.054*
C170.1750 (3)0.0755 (2)0.5146 (5)0.0524 (10)
H17A0.16550.08610.39900.079*
H17B0.10480.05860.55830.079*
H17C0.23350.04270.52640.079*
C120.2251 (3)0.12299 (19)0.7966 (5)0.0451 (9)
H12A0.25760.16160.85000.054*
H12B0.27930.08710.80780.054*
C110.1160 (3)0.10403 (18)0.8883 (4)0.0452 (9)
H11A0.13280.09751.00530.054*
H11B0.08740.06260.84410.054*
C90.0250 (3)0.15693 (17)0.8707 (4)0.0378 (8)
H90.05710.19760.91780.045*
C30.2589 (3)0.0560 (2)1.1203 (5)0.0484 (9)
H3A0.22780.01301.08730.058*
C20.1724 (4)0.0901 (2)1.2283 (4)0.0551 (10)
H2A0.20470.13051.27290.066*
H2B0.15240.06161.32090.066*
C10.0659 (3)0.1064 (2)1.1279 (4)0.0470 (9)
H1A0.01550.13281.19650.056*
H1B0.02670.06551.10170.056*
C180.3753 (3)0.05838 (19)0.8587 (5)0.0509 (10)
H18A0.34460.01650.82450.076*
H18B0.39610.08360.76230.076*
H18C0.44130.05120.92660.076*
C100.0891 (3)0.14398 (16)0.9648 (4)0.0369 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0368 (17)0.127 (3)0.086 (2)0.0117 (19)0.0003 (15)0.031 (2)
O1W0.069 (2)0.074 (2)0.089 (2)0.0153 (19)0.0203 (19)0.0232 (19)
O60.0449 (17)0.0399 (14)0.0757 (17)0.0003 (12)0.0139 (14)0.0154 (14)
O30.0512 (17)0.0487 (15)0.0500 (13)0.0058 (13)0.0075 (12)0.0081 (12)
O20.0395 (15)0.0459 (14)0.0592 (14)0.0041 (12)0.0062 (12)0.0076 (13)
O10.065 (2)0.077 (2)0.0685 (16)0.0089 (17)0.0245 (16)0.0128 (17)
O50.048 (2)0.0454 (15)0.132 (3)0.0037 (14)0.023 (2)0.0110 (19)
C160.032 (3)0.092 (3)0.087 (3)0.002 (2)0.001 (2)0.039 (3)
C150.041 (2)0.050 (2)0.0531 (18)0.0046 (18)0.0021 (17)0.0046 (19)
C130.036 (2)0.0381 (18)0.0458 (17)0.0031 (16)0.0003 (15)0.0002 (17)
C140.043 (2)0.0390 (19)0.0428 (16)0.0022 (17)0.0015 (15)0.0073 (16)
C80.041 (2)0.0312 (17)0.0386 (16)0.0049 (16)0.0005 (15)0.0016 (15)
C70.042 (2)0.046 (2)0.0368 (15)0.0015 (18)0.0018 (15)0.0060 (16)
C60.041 (2)0.0373 (18)0.0407 (17)0.0046 (16)0.0039 (15)0.0002 (16)
C50.038 (2)0.0268 (16)0.0421 (16)0.0031 (15)0.0026 (15)0.0025 (15)
C40.042 (2)0.0311 (17)0.0476 (17)0.0004 (16)0.0011 (16)0.0006 (17)
C190.047 (3)0.037 (2)0.068 (2)0.0014 (19)0.013 (2)0.001 (2)
C200.043 (2)0.0408 (19)0.0514 (17)0.0035 (17)0.0050 (16)0.0084 (17)
C170.047 (2)0.050 (2)0.060 (2)0.0033 (19)0.0058 (19)0.0124 (19)
C120.043 (2)0.044 (2)0.0484 (18)0.0066 (17)0.0026 (17)0.0041 (18)
C110.046 (2)0.047 (2)0.0426 (16)0.0113 (18)0.0031 (16)0.0064 (17)
C90.038 (2)0.0358 (17)0.0393 (16)0.0004 (16)0.0049 (14)0.0020 (16)
C30.049 (2)0.044 (2)0.0513 (18)0.0001 (19)0.0096 (18)0.008 (2)
C20.065 (3)0.063 (2)0.0371 (16)0.000 (2)0.0040 (18)0.0058 (19)
C10.050 (2)0.056 (2)0.0355 (16)0.0009 (19)0.0043 (16)0.0013 (18)
C180.050 (3)0.040 (2)0.063 (2)0.0059 (18)0.001 (2)0.000 (2)
C100.041 (2)0.0342 (17)0.0356 (15)0.0028 (16)0.0016 (15)0.0012 (15)
Geometric parameters (Å, º) top
O4—C161.425 (5)C5—C41.542 (5)
O4—H40.8200C5—H50.9800
O1W—H1W0.95 (6)C4—C191.508 (5)
O1W—H2W0.84 (6)C4—C181.524 (5)
O6—C191.345 (5)C4—C31.568 (5)
O6—C201.451 (5)C20—C101.529 (5)
O3—C151.440 (4)C20—H20A0.9700
O3—H30.8200C20—H20B0.9700
O2—C61.452 (4)C17—H17A0.9600
O2—H20.8200C17—H17B0.9600
O1—C31.422 (5)C17—H17C0.9600
O1—H10.8200C12—C111.528 (5)
O5—C191.208 (5)C12—H12A0.9700
C16—C151.496 (6)C12—H12B0.9700
C16—H16A0.9700C11—C91.519 (5)
C16—H16B0.9700C11—H11A0.9700
C15—C131.546 (5)C11—H11B0.9700
C15—H150.9800C9—C101.562 (5)
C13—C171.534 (5)C9—H90.9800
C13—C121.537 (5)C3—C21.504 (6)
C13—C141.544 (5)C3—H3A0.9800
C14—C81.502 (5)C2—C11.525 (5)
C14—H14A0.9700C2—H2A0.9700
C14—H14B0.9700C2—H2B0.9700
C8—C71.314 (5)C1—C101.540 (5)
C8—C91.517 (4)C1—H1A0.9700
C7—C61.490 (5)C1—H1B0.9700
C7—H70.9300C18—H18A0.9600
C6—C51.538 (4)C18—H18B0.9600
C6—H60.9800C18—H18C0.9600
C5—C101.534 (5)
C16—O4—H4109.5C10—C20—H20A108.4
H1W—O1W—H2W113 (6)O6—C20—H20B108.4
C19—O6—C20123.2 (3)C10—C20—H20B108.4
C15—O3—H3109.5H20A—C20—H20B107.4
C6—O2—H2109.5C13—C17—H17A109.5
C3—O1—H1109.5C13—C17—H17B109.5
O4—C16—C15112.0 (4)H17A—C17—H17B109.5
O4—C16—H16A109.2C13—C17—H17C109.5
C15—C16—H16A109.2H17A—C17—H17C109.5
O4—C16—H16B109.2H17B—C17—H17C109.5
C15—C16—H16B109.2C11—C12—C13114.6 (3)
H16A—C16—H16B107.9C11—C12—H12A108.6
O3—C15—C16106.8 (3)C13—C12—H12A108.6
O3—C15—C13110.6 (3)C11—C12—H12B108.6
C16—C15—C13114.7 (3)C13—C12—H12B108.6
O3—C15—H15108.2H12A—C12—H12B107.6
C16—C15—H15108.2C9—C11—C12111.6 (3)
C13—C15—H15108.2C9—C11—H11A109.3
C17—C13—C12111.0 (3)C12—C11—H11A109.3
C17—C13—C14110.3 (3)C9—C11—H11B109.3
C12—C13—C14107.0 (3)C12—C11—H11B109.3
C17—C13—C15110.7 (3)H11A—C11—H11B108.0
C12—C13—C15109.3 (3)C8—C9—C11107.8 (3)
C14—C13—C15108.5 (3)C8—C9—C10112.8 (3)
C8—C14—C13112.0 (3)C11—C9—C10116.2 (3)
C8—C14—H14A109.2C8—C9—H9106.5
C13—C14—H14A109.2C11—C9—H9106.5
C8—C14—H14B109.2C10—C9—H9106.5
C13—C14—H14B109.2O1—C3—C2108.9 (3)
H14A—C14—H14B107.9O1—C3—C4111.1 (3)
C7—C8—C14122.2 (3)C2—C3—C4112.3 (3)
C7—C8—C9123.8 (3)O1—C3—H3A108.1
C14—C8—C9113.8 (3)C2—C3—H3A108.1
C8—C7—C6125.6 (3)C4—C3—H3A108.1
C8—C7—H7117.2C3—C2—C1110.4 (3)
C6—C7—H7117.2C3—C2—H2A109.6
O2—C6—C7108.4 (3)C1—C2—H2A109.6
O2—C6—C5111.6 (3)C3—C2—H2B109.6
C7—C6—C5111.9 (3)C1—C2—H2B109.6
O2—C6—H6108.3H2A—C2—H2B108.1
C7—C6—H6108.3C2—C1—C10114.3 (3)
C5—C6—H6108.3C2—C1—H1A108.7
C10—C5—C6114.3 (3)C10—C1—H1A108.7
C10—C5—C4109.4 (3)C2—C1—H1B108.7
C6—C5—C4112.6 (3)C10—C1—H1B108.7
C10—C5—H5106.7H1A—C1—H1B107.6
C6—C5—H5106.7C4—C18—H18A109.5
C4—C5—H5106.7C4—C18—H18B109.5
C19—C4—C18110.6 (3)H18A—C18—H18B109.5
C19—C4—C5110.2 (3)C4—C18—H18C109.5
C18—C4—C5111.8 (3)H18A—C18—H18C109.5
C19—C4—C3106.6 (3)H18B—C18—H18C109.5
C18—C4—C3108.5 (3)C20—C10—C5107.4 (3)
C5—C4—C3108.9 (3)C20—C10—C1110.1 (3)
O5—C19—O6116.5 (3)C5—C10—C1109.9 (3)
O5—C19—C4123.5 (4)C20—C10—C9106.8 (3)
O6—C19—C4119.7 (4)C5—C10—C9112.4 (3)
O6—C20—C10115.6 (3)C1—C10—C9110.1 (3)
O6—C20—H20A108.4
O4—C16—C15—O363.3 (5)C14—C13—C12—C1153.3 (4)
O4—C16—C15—C13173.8 (4)C15—C13—C12—C11170.6 (3)
O3—C15—C13—C1757.3 (4)C13—C12—C11—C956.2 (4)
C16—C15—C13—C1763.5 (5)C7—C8—C9—C11118.5 (4)
O3—C15—C13—C12179.8 (3)C14—C8—C9—C1157.6 (4)
C16—C15—C13—C1259.0 (4)C7—C8—C9—C1011.1 (5)
O3—C15—C13—C1463.9 (4)C14—C8—C9—C10172.8 (3)
C16—C15—C13—C14175.3 (4)C12—C11—C9—C854.4 (4)
C17—C13—C14—C867.1 (4)C12—C11—C9—C10178.0 (3)
C12—C13—C14—C853.6 (4)C19—C4—C3—O162.3 (4)
C15—C13—C14—C8171.4 (3)C18—C4—C3—O156.8 (4)
C13—C14—C8—C7116.7 (4)C5—C4—C3—O1178.8 (3)
C13—C14—C8—C959.5 (4)C19—C4—C3—C260.0 (4)
C14—C8—C7—C6176.0 (3)C18—C4—C3—C2179.2 (3)
C9—C8—C7—C60.2 (6)C5—C4—C3—C258.9 (4)
C8—C7—C6—O2109.2 (4)O1—C3—C2—C1177.0 (3)
C8—C7—C6—C514.4 (5)C4—C3—C2—C153.5 (4)
O2—C6—C5—C1081.9 (4)C3—C2—C1—C1051.8 (5)
C7—C6—C5—C1039.8 (4)O6—C20—C10—C544.9 (4)
O2—C6—C5—C443.7 (4)O6—C20—C10—C174.8 (4)
C7—C6—C5—C4165.5 (3)O6—C20—C10—C9165.7 (3)
C10—C5—C4—C1956.3 (4)C6—C5—C10—C2065.7 (3)
C6—C5—C4—C1972.0 (4)C4—C5—C10—C2061.6 (3)
C10—C5—C4—C18179.8 (3)C6—C5—C10—C1174.4 (3)
C6—C5—C4—C1851.5 (4)C4—C5—C10—C158.3 (4)
C10—C5—C4—C360.3 (3)C6—C5—C10—C951.4 (4)
C6—C5—C4—C3171.4 (3)C4—C5—C10—C9178.8 (3)
C20—O6—C19—O5168.2 (4)C2—C1—C10—C2063.6 (4)
C20—O6—C19—C418.1 (5)C2—C1—C10—C554.6 (4)
C18—C4—C19—O528.6 (6)C2—C1—C10—C9179.0 (3)
C5—C4—C19—O5152.8 (4)C8—C9—C10—C2081.8 (3)
C3—C4—C19—O589.2 (5)C11—C9—C10—C20153.0 (3)
C18—C4—C19—O6158.1 (3)C8—C9—C10—C535.7 (4)
C5—C4—C19—O633.9 (5)C11—C9—C10—C589.4 (4)
C3—C4—C19—O684.1 (4)C8—C9—C10—C1158.6 (3)
C19—O6—C20—C1024.0 (5)C11—C9—C10—C133.5 (4)
C17—C13—C12—C1167.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1W0.821.962.754 (5)163
O2—H2···O4i0.822.042.855 (4)172
O3—H3···O2ii0.8222.821 (4)174
O4—H4···O1iii0.822.723.532 (5)171
O1W—H1W···O1iv0.95 (6)2.61 (6)3.200 (5)121 (5)
O1W—H1W···O5iv0.95 (6)2.01 (6)2.881 (4)153 (5)
O1W—H2W···O3v0.84 (6)1.98 (7)2.787 (4)160 (6)
Symmetry codes: (i) x+1, y, z; (ii) x1/2, y+1/2, z+1; (iii) x1, y, z1; (iv) x+1, y, z; (v) x, y, z+1.
 

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