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In the crystal structure of the title compound, 4,12,20-tri­hydroxy-3,5,8,11,13,16,19,21,24-nona­methyl-1,9,17-trioxa­cyclo­tetra­cosane-2,10,18-trione-methanol-water (1/2/1), C30H54O9·2CH4O·H2O, the mol­ecules are packed parallel to [100], with various hydrogen bonds to trapped CH3OH and H2O solvent mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008055/bt6265sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008055/bt6265Isup2.hkl
Contains datablock I

CCDC reference: 214609

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.008 Å
  • H-atom completeness 97%
  • R factor = 0.050
  • wR factor = 0.085
  • Data-to-parameter ratio = 11.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.108 General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C32 H64 O12 Atom count from the _atom_site data: C32 H62 O12 CELLZ_01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C32 H64 O12 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 128.00 128.00 0.00 H 256.00 248.00 8.00 O 48.00 48.00 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional? REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.11 From the CIF: _reflns_number_total 4594 Count of symmetry unique reflns 4610 Completeness (_total/calc) 99.65% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

In an earlier work, we reported on the isolation of dasypogalactone from the Indonesian lichen Usnea Dasypoga Rohl. and proposed its molecular structure from mass spectra and NMR data (Suwarso et al., 1999). However, the configuration of dasypogalactone was not fully established. Now, we succeeded in growing crystals, still of minor quality and scattering power [only 1961 intensities with I > 2σ(I)], but at least suitable for a single-crystal X-ray analysis. It was not possible to determine the absolute configuration but the former structure was confirmed with correct relative configurations assigned as (2,3,7R*)(4S*)-3,7-dihydroxy-2,4-dimethyloctanoic acid for the monomeric acid unit (see Scheme). The molecule shows non-crystallographic C3 symmetry, with the OH groups (O3, O6, O9; numbering see Fig. 1) lying in the ring plane and directed towards the ring centre. Their intramolecular non-bonding distances are O3.·O6 = 3.966 (5), O3.·O9 = 3.544 (5) and O6.·O9 = 3.978 (5) Å. Carboxylic acid O atoms O2, O5 and O8 point to one side of the ring plane and the three methyl groups C6, C16 and C26 to the other one. The three subparts of the ring show almost equal bond geometries regarding the 3σ criterion. In the crystal, the molecules are packed head-to-tail along [100] (Fig. 2) with a plane-to-plane distance of 8.898 (1) Å. Enclosed solvent molecules, which count one water and two methanol per asymmetric unit, are linked to this host lattice by various hydrogen bonds. The MeOH solvent 2 (C200/O200) is situated in a sandwich manner midway between two dasypogalactone rings (Fig. 3) with distances of 4.390 (7) and 4.327 (5) Å for C200 and O200, respectively, above the plane defined by O3, O6 and O9. This solvent molecule shows an O200—H200···O300 hydrogen bond to the water atom O300 with H200···O300 = 1.84 Å and angle = 160.1°, and a weak C200—H20E···O2 interaction of 2.43 Å and angle = 157.6°. Atoms C100 and O100 of methanol 1 lie 2.601 (7) and 2.181 (5) Å above the named plane. The accompanying hydrogen bonds are O100—H100.·O9 of 1.95 Å and angle = 148.7°, and C100—H10D.·O6 of 2.37 Å and angle = 167.4°. The water atom O300, finally, is located 6.967 (4) Å above the O3/O6/O9 plane and additional hydrogen bonds are O6—H6.·O300(x + 1, y, z) of 2.08 Å and angle = 153.6° and O9—H9.·O300(x + 1, y, z) of 2.12 Å and angle = 125.9°. It was not possible to locate the water H atoms. All these values are normalized for C—H = 1.08 Å and O—H = 0.938 Å. A somewhat similar packing of C3 symmetric macrolides with trapped water and methanol solvent molecules was described recently (Burke & Zhao, 2000).

Experimental top

Isolation of the compound has already been described by Suwarso et al. (1999). The product was crystallized from CH2Cl2/CH3OH solution.

Refinement top

H atoms were refined at calculated positions riding on the C or O atoms, with isotropic displacement parameters Uiso(H) = 1.2Ueq(C) or 1.5Ueq(CH3/OH). All CH3 and OH H atoms were allowed to rotate but not to tip. The H atoms of the water molecule could not be located and were therefore omitted from the refinement. The title compound crystallizes in the polar space group P212121; however, in the absence of significant anomalous scattering effects, the Flack (1983) parameter is essentially meaningless. Accordingly, Friedel pairs were merged.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram, viewed along [100], with H atoms omitted.
[Figure 3] Fig. 3. The position of the solvent molecules between two dasypogalactone rings.
4,12,20-trihydroxy-3,5,8,11,13,16,19,21,24-nonamethyl-1,9,17- trioxacyclotetracosane-2,10,18-trione–methanol–water (1/2/1) top
Crystal data top
C30H54O9·2CH4O·H2ODx = 1.143 Mg m3
Mr = 640.83Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 713 reflections
a = 8.8977 (14) Åθ = 2.5–12.7°
b = 19.524 (3) ŵ = 0.09 mm1
c = 21.445 (3) ÅT = 153 K
V = 3725.5 (10) Å3Block, colourless
Z = 40.32 × 0.25 × 0.15 mm
F(000) = 1408
Data collection top
Bruker SMART CCD area-detector
diffractometer
4594 independent reflections
Radiation source: sealed tube1359 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.108
π and ω scansθmax = 27.1°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 118
Tmin = 0.906, Tmax = 0.953k = 2424
22975 measured reflectionsl = 2726
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: geom and difmap
wR(F2) = 0.085H-atom parameters constrained
S = 0.86 w = 1/[σ2(Fo2) + (0.0003P)2]
where P = (Fo2 + 2Fc2)/3
4594 reflections(Δ/σ)max < 0.001
413 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C30H54O9·2CH4O·H2OV = 3725.5 (10) Å3
Mr = 640.83Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.8977 (14) ŵ = 0.09 mm1
b = 19.524 (3) ÅT = 153 K
c = 21.445 (3) Å0.32 × 0.25 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4594 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
1359 reflections with I > 2σ(I)
Tmin = 0.906, Tmax = 0.953Rint = 0.108
22975 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 0.86Δρmax = 0.17 e Å3
4594 reflectionsΔρmin = 0.17 e Å3
413 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0931 (4)1.0277 (2)0.26806 (18)0.0401 (12)
O20.2940 (5)0.9607 (2)0.2519 (2)0.0675 (17)
O30.0506 (4)0.9515 (2)0.13037 (18)0.0447 (12)
H30.13090.96270.11240.067*
O40.1150 (4)0.7852 (2)0.04383 (19)0.0411 (12)
O50.0325 (5)0.7908 (2)0.12820 (19)0.0540 (14)
O60.0238 (5)0.9389 (2)0.05163 (18)0.0475 (12)
H60.07680.96580.03040.071*
O70.0170 (4)1.20544 (19)0.08711 (17)0.0359 (12)
O80.2215 (5)1.1860 (2)0.05796 (18)0.0504 (14)
O90.0623 (5)1.1075 (2)0.04613 (15)0.0453 (12)
H90.00331.09250.07080.068*
C10.1602 (8)0.9694 (4)0.2521 (3)0.044 (2)
C20.0505 (7)0.9135 (3)0.2364 (2)0.0375 (18)
H2A0.05350.93240.23960.045*
C30.0650 (7)0.8536 (3)0.2819 (2)0.057 (2)
H3A0.16270.83130.27610.086*
H3B0.01550.82050.27400.086*
H3C0.05700.87070.32480.086*
C40.0770 (7)0.8909 (3)0.1691 (2)0.0383 (18)
H4A0.18480.87710.16460.046*
C50.0213 (7)0.8318 (3)0.1466 (3)0.0374 (18)
H5A0.00480.79030.17170.045*
C60.1873 (7)0.8451 (3)0.1543 (3)0.060 (2)
H6A0.21540.88610.13070.089*
H6B0.21010.85220.19860.089*
H6C0.24420.80570.13870.089*
C70.0119 (7)0.8163 (3)0.0787 (2)0.047 (2)
H7A0.03870.85140.05280.056*
H7B0.12140.82130.07200.056*
C80.0347 (7)0.7469 (3)0.0553 (3)0.0459 (19)
H8A0.14250.73990.06470.055*
H8B0.02290.71140.07800.055*
C90.0102 (7)0.7377 (3)0.0136 (3)0.045 (2)
H9A0.09530.75070.02440.054*
C100.0412 (7)0.6651 (3)0.0362 (2)0.058 (2)
H10A0.14030.65040.02140.086*
H10B0.03590.63410.01990.086*
H10C0.03930.66410.08190.086*
C110.0740 (8)0.8112 (4)0.0988 (3)0.041 (2)
C120.1748 (7)0.8686 (3)0.1191 (3)0.0336 (17)
H12A0.26320.87150.09050.040*
C130.2289 (7)0.8572 (3)0.1855 (2)0.052 (2)
H13A0.14260.85750.21390.078*
H13B0.29870.89380.19720.078*
H13C0.28020.81290.18820.078*
C140.0838 (7)0.9346 (3)0.1150 (2)0.0375 (18)
H14A0.00470.92850.14320.045*
C150.1576 (7)1.0013 (3)0.1339 (2)0.0317 (17)
H15A0.17870.99780.17960.038*
C160.3102 (7)1.0128 (3)0.1015 (2)0.053 (2)
H16A0.29531.01520.05630.079*
H16B0.37790.97470.11140.079*
H16C0.35451.05580.11620.079*
C170.0538 (6)1.0610 (3)0.1256 (3)0.0393 (17)
H17A0.04961.04540.13490.047*
H17B0.05611.07450.08110.047*
C180.0857 (7)1.1245 (3)0.1648 (2)0.0384 (18)
H18A0.07471.11240.20940.046*
H18B0.19141.13850.15800.046*
C190.0144 (7)1.1841 (3)0.1508 (2)0.0428 (19)
H190.12181.16940.15410.051*
C200.0123 (7)1.2439 (3)0.1937 (2)0.054 (2)
H20A0.11471.26110.18770.081*
H20B0.00041.22910.23710.081*
H20C0.06001.28030.18430.081*
C210.0912 (8)1.2026 (3)0.0463 (3)0.0319 (17)
C220.0426 (7)1.2242 (3)0.0182 (2)0.0343 (17)
H22A0.06941.22070.02050.041*
C230.0862 (7)1.2989 (3)0.0300 (2)0.0463 (19)
H23A0.19591.30280.03210.069*
H23B0.04251.31420.06960.069*
H23C0.04821.32760.00400.069*
C240.1093 (7)1.1750 (3)0.0659 (2)0.0310 (17)
H24A0.22121.17730.06230.037*
C250.0681 (6)1.1876 (3)0.1342 (3)0.0367 (17)
H25A0.11001.23310.14670.044*
C260.1029 (6)1.1896 (3)0.1438 (2)0.049 (2)
H26A0.14761.14730.12760.074*
H26B0.14501.22900.12150.074*
H26C0.12511.19370.18840.074*
C270.1407 (7)1.1323 (3)0.1756 (2)0.0419 (19)
H27A0.09101.08800.16680.050*
H27B0.24761.12770.16340.050*
C280.1336 (7)1.1454 (3)0.2464 (2)0.0358 (18)
H28A0.19491.18620.25660.043*
H28B0.02841.15520.25850.043*
C290.1896 (7)1.0856 (3)0.2827 (3)0.0373 (18)
H290.29581.07520.27100.045*
C300.1781 (6)1.0975 (3)0.3525 (2)0.048 (2)
H30A0.07371.10790.36360.072*
H30B0.24251.13610.36430.072*
H30C0.21081.05630.37470.072*
C1000.3127 (8)1.0062 (3)0.0032 (2)0.090 (3)
H10D0.22490.98480.02270.135*
H10E0.40230.97860.01180.135*
H10F0.32651.05230.02020.135*
O1000.2907 (6)1.0102 (3)0.06082 (19)0.0747 (17)
H1000.21081.03180.06820.112*
C2000.5930 (10)1.0304 (4)0.1713 (3)0.118 (4)
H20D0.69631.01440.17760.177*
H20E0.52310.99910.19210.177*
H20F0.58201.07640.18890.177*
O2000.5616 (7)1.0322 (4)0.1082 (2)0.123 (2)
H2000.63611.01760.08820.185*
O3000.8376 (4)1.0096 (2)0.05529 (16)0.0532 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.032 (3)0.041 (3)0.047 (3)0.001 (3)0.001 (3)0.003 (2)
O20.035 (3)0.072 (4)0.095 (4)0.002 (3)0.016 (3)0.022 (3)
O30.043 (3)0.051 (3)0.040 (3)0.015 (3)0.006 (3)0.009 (2)
O40.030 (3)0.044 (3)0.049 (3)0.003 (2)0.003 (3)0.000 (3)
O50.050 (3)0.048 (3)0.064 (3)0.014 (3)0.022 (3)0.006 (3)
O60.047 (3)0.032 (3)0.063 (3)0.003 (2)0.004 (3)0.003 (2)
O70.032 (3)0.047 (3)0.029 (2)0.010 (3)0.009 (2)0.002 (2)
O80.041 (3)0.075 (4)0.035 (3)0.001 (3)0.001 (3)0.006 (3)
O90.049 (3)0.058 (3)0.030 (3)0.012 (3)0.006 (3)0.002 (2)
C10.034 (5)0.055 (6)0.043 (5)0.006 (5)0.002 (5)0.014 (4)
C20.037 (5)0.037 (4)0.039 (4)0.002 (4)0.001 (4)0.012 (3)
C30.075 (6)0.041 (5)0.055 (4)0.011 (4)0.006 (5)0.010 (4)
C40.036 (5)0.046 (5)0.034 (4)0.001 (4)0.010 (4)0.013 (4)
C50.038 (5)0.034 (4)0.041 (4)0.001 (4)0.008 (4)0.004 (4)
C60.048 (5)0.061 (6)0.070 (5)0.001 (4)0.003 (5)0.010 (4)
C70.038 (5)0.045 (5)0.058 (5)0.013 (4)0.002 (4)0.007 (4)
C80.047 (5)0.036 (5)0.055 (5)0.013 (4)0.009 (4)0.000 (4)
C90.032 (5)0.030 (5)0.073 (5)0.012 (4)0.019 (4)0.008 (4)
C100.046 (5)0.049 (5)0.078 (5)0.001 (4)0.017 (5)0.001 (4)
C110.049 (6)0.039 (5)0.036 (5)0.013 (5)0.011 (4)0.004 (4)
C120.025 (4)0.041 (5)0.036 (4)0.004 (4)0.004 (4)0.002 (4)
C130.058 (6)0.051 (5)0.046 (4)0.013 (4)0.006 (4)0.011 (4)
C140.040 (5)0.051 (5)0.022 (4)0.004 (4)0.004 (4)0.006 (4)
C150.038 (5)0.033 (4)0.023 (3)0.005 (4)0.005 (4)0.001 (4)
C160.049 (5)0.049 (5)0.060 (5)0.002 (4)0.000 (4)0.001 (4)
C170.032 (4)0.041 (4)0.045 (4)0.004 (4)0.002 (4)0.009 (4)
C180.038 (5)0.050 (5)0.026 (4)0.007 (4)0.005 (4)0.011 (4)
C190.040 (5)0.052 (5)0.036 (4)0.014 (4)0.005 (4)0.000 (4)
C200.061 (5)0.048 (5)0.054 (5)0.003 (4)0.003 (4)0.016 (4)
C210.041 (5)0.016 (4)0.039 (5)0.002 (4)0.002 (4)0.008 (4)
C220.026 (4)0.036 (4)0.041 (4)0.003 (4)0.005 (4)0.003 (4)
C230.051 (5)0.036 (4)0.052 (4)0.001 (4)0.001 (4)0.002 (4)
C240.034 (4)0.021 (4)0.037 (4)0.008 (4)0.001 (4)0.002 (3)
C250.033 (5)0.037 (5)0.040 (4)0.000 (4)0.012 (4)0.006 (4)
C260.051 (5)0.060 (5)0.035 (4)0.003 (4)0.007 (4)0.000 (4)
C270.039 (5)0.042 (5)0.045 (4)0.003 (4)0.000 (4)0.002 (4)
C280.030 (4)0.041 (5)0.036 (4)0.005 (4)0.002 (4)0.003 (4)
C290.036 (5)0.034 (5)0.043 (4)0.010 (4)0.002 (4)0.002 (4)
C300.030 (4)0.070 (6)0.044 (4)0.008 (4)0.000 (4)0.004 (4)
C1000.140 (9)0.077 (6)0.053 (5)0.035 (7)0.013 (6)0.015 (5)
O1000.094 (5)0.064 (4)0.066 (3)0.019 (4)0.042 (3)0.001 (3)
C2000.116 (9)0.155 (9)0.083 (6)0.021 (8)0.010 (7)0.007 (7)
O2000.085 (5)0.215 (7)0.070 (4)0.023 (5)0.011 (4)0.003 (5)
O3000.042 (3)0.068 (3)0.050 (3)0.006 (3)0.005 (3)0.001 (3)
Geometric parameters (Å, º) top
O1—C11.330 (7)C15—H15A1.0000
O1—C291.455 (6)C16—H16A0.9800
O2—C11.203 (7)C16—H16B0.9800
O3—C41.464 (5)C16—H16C0.9800
O3—H30.8400C17—C181.526 (6)
O4—C111.336 (6)C17—H17A0.9900
O4—C91.467 (6)C17—H17B0.9900
O5—C111.205 (7)C18—C191.496 (7)
O6—C141.462 (6)C18—H18A0.9900
O6—H60.8400C18—H18B0.9900
O7—C211.303 (6)C19—C201.504 (6)
O7—C191.456 (5)C19—H191.0000
O8—C211.230 (6)C20—H20A0.9800
O9—C241.446 (5)C20—H20B0.9800
O9—H90.8400C20—H20C0.9800
C1—C21.502 (8)C21—C221.508 (7)
C2—C41.527 (6)C22—C241.525 (6)
C2—C31.528 (6)C22—C231.530 (6)
C2—H2A1.0000C22—H22A1.0000
C3—H3A0.9800C23—H23A0.9800
C3—H3B0.9800C23—H23B0.9800
C3—H3C0.9800C23—H23C0.9800
C4—C51.526 (7)C24—C251.528 (6)
C4—H4A1.0000C24—H24A1.0000
C5—C61.508 (7)C25—C261.536 (7)
C5—C71.516 (7)C25—C271.540 (7)
C5—H5A1.0000C25—H25A1.0000
C6—H6A0.9800C26—H26A0.9800
C6—H6B0.9800C26—H26B0.9800
C6—H6C0.9800C26—H26C0.9800
C7—C81.503 (6)C27—C281.540 (5)
C7—H7A0.9900C27—H27A0.9900
C7—H7B0.9900C27—H27B0.9900
C8—C91.504 (7)C28—C291.490 (6)
C8—H8A0.9900C28—H28A0.9900
C8—H8B0.9900C28—H28B0.9900
C9—C101.523 (6)C29—C301.518 (6)
C9—H9A1.0000C29—H291.0000
C10—H10A0.9800C30—H30A0.9800
C10—H10B0.9800C30—H30B0.9800
C10—H10C0.9800C30—H30C0.9800
C11—C121.500 (8)C100—O1001.389 (5)
C12—C131.519 (6)C100—H10D0.9800
C12—C141.525 (7)C100—H10E0.9800
C12—H12A1.0000C100—H10F0.9800
C13—H13A0.9800O100—H1000.8400
C13—H13B0.9800C200—O2001.382 (6)
C13—H13C0.9800C200—H20D0.9800
C14—C151.512 (7)C200—H20E0.9800
C14—H14A1.0000C200—H20F0.9800
C15—C171.497 (7)O200—H2000.8400
C15—C161.542 (6)
C1—O1—C29117.2 (5)C15—C17—C18116.9 (5)
C4—O3—H3109.5C15—C17—H17A108.1
C11—O4—C9117.2 (5)C18—C17—H17A108.1
C14—O6—H6109.5C15—C17—H17B108.1
C21—O7—C19118.5 (5)C18—C17—H17B108.1
C24—O9—H9109.5H17A—C17—H17B107.3
O2—C1—O1124.4 (7)C19—C18—C17114.3 (5)
O2—C1—C2122.7 (7)C19—C18—H18A108.7
O1—C1—C2112.8 (6)C17—C18—H18A108.7
C1—C2—C4108.8 (5)C19—C18—H18B108.7
C1—C2—C3111.0 (5)C17—C18—H18B108.7
C4—C2—C3111.7 (5)H18A—C18—H18B107.6
C1—C2—H2A108.4O7—C19—C18107.2 (5)
C4—C2—H2A108.4O7—C19—C20108.8 (5)
C3—C2—H2A108.4C18—C19—C20112.8 (5)
C2—C3—H3A109.5O7—C19—H19109.4
C2—C3—H3B109.5C18—C19—H19109.4
H3A—C3—H3B109.5C20—C19—H19109.4
C2—C3—H3C109.5C19—C20—H20A109.5
H3A—C3—H3C109.5C19—C20—H20B109.5
H3B—C3—H3C109.5H20A—C20—H20B109.5
O3—C4—C2106.1 (5)C19—C20—H20C109.5
O3—C4—C5109.8 (5)H20A—C20—H20C109.5
C2—C4—C5115.4 (5)H20B—C20—H20C109.5
O3—C4—H4A108.4O8—C21—O7124.8 (6)
C2—C4—H4A108.4O8—C21—C22122.1 (6)
C5—C4—H4A108.4O7—C21—C22113.1 (6)
C6—C5—C7109.3 (6)C21—C22—C24109.1 (5)
C6—C5—C4113.4 (5)C21—C22—C23110.2 (5)
C7—C5—C4110.1 (5)C24—C22—C23113.0 (5)
C6—C5—H5A108.0C21—C22—H22A108.1
C7—C5—H5A108.0C24—C22—H22A108.1
C4—C5—H5A108.0C23—C22—H22A108.1
C5—C6—H6A109.5C22—C23—H23A109.5
C5—C6—H6B109.5C22—C23—H23B109.5
H6A—C6—H6B109.5H23A—C23—H23B109.5
C5—C6—H6C109.5C22—C23—H23C109.5
H6A—C6—H6C109.5H23A—C23—H23C109.5
H6B—C6—H6C109.5H23B—C23—H23C109.5
C8—C7—C5116.6 (5)O9—C24—C22105.3 (4)
C8—C7—H7A108.1O9—C24—C25111.0 (5)
C5—C7—H7A108.1C22—C24—C25116.7 (5)
C8—C7—H7B108.1O9—C24—H24A107.8
C5—C7—H7B108.1C22—C24—H24A107.8
H7A—C7—H7B107.3C25—C24—H24A107.8
C7—C8—C9113.3 (5)C24—C25—C26111.7 (5)
C7—C8—H8A108.9C24—C25—C27109.9 (5)
C9—C8—H8A108.9C26—C25—C27110.8 (5)
C7—C8—H8B108.9C24—C25—H25A108.1
C9—C8—H8B108.9C26—C25—H25A108.1
H8A—C8—H8B107.7C27—C25—H25A108.1
O4—C9—C8105.5 (5)C25—C26—H26A109.5
O4—C9—C10109.4 (5)C25—C26—H26B109.5
C8—C9—C10113.5 (5)H26A—C26—H26B109.5
O4—C9—H9A109.5C25—C26—H26C109.5
C8—C9—H9A109.5H26A—C26—H26C109.5
C10—C9—H9A109.5H26B—C26—H26C109.5
C9—C10—H10A109.5C28—C27—C25115.8 (5)
C9—C10—H10B109.5C28—C27—H27A108.3
H10A—C10—H10B109.5C25—C27—H27A108.3
C9—C10—H10C109.5C28—C27—H27B108.3
H10A—C10—H10C109.5C25—C27—H27B108.3
H10B—C10—H10C109.5H27A—C27—H27B107.4
O5—C11—O4123.4 (7)C29—C28—C27111.8 (5)
O5—C11—C12124.4 (6)C29—C28—H28A109.3
O4—C11—C12112.1 (6)C27—C28—H28A109.3
C11—C12—C13110.6 (5)C29—C28—H28B109.3
C11—C12—C14107.3 (5)C27—C28—H28B109.3
C13—C12—C14110.3 (5)H28A—C28—H28B107.9
C11—C12—H12A109.5O1—C29—C28107.4 (5)
C13—C12—H12A109.5O1—C29—C30107.0 (5)
C14—C12—H12A109.5C28—C29—C30112.0 (5)
C12—C13—H13A109.5O1—C29—H29110.1
C12—C13—H13B109.5C28—C29—H29110.1
H13A—C13—H13B109.5C30—C29—H29110.1
C12—C13—H13C109.5C29—C30—H30A109.5
H13A—C13—H13C109.5C29—C30—H30B109.5
H13B—C13—H13C109.5H30A—C30—H30B109.5
O6—C14—C15111.0 (5)C29—C30—H30C109.5
O6—C14—C12107.2 (5)H30A—C30—H30C109.5
C15—C14—C12118.8 (5)H30B—C30—H30C109.5
O6—C14—H14A106.4O100—C100—H10D109.5
C15—C14—H14A106.4O100—C100—H10E109.5
C12—C14—H14A106.4H10D—C100—H10E109.5
C17—C15—C14111.7 (5)O100—C100—H10F109.5
C17—C15—C16112.1 (5)H10D—C100—H10F109.5
C14—C15—C16112.7 (5)H10E—C100—H10F109.5
C17—C15—H15A106.6C100—O100—H100109.5
C14—C15—H15A106.6O200—C200—H20D109.5
C16—C15—H15A106.6O200—C200—H20E109.5
C15—C16—H16A109.5H20D—C200—H20E109.5
C15—C16—H16B109.5O200—C200—H20F109.5
H16A—C16—H16B109.5H20D—C200—H20F109.5
C15—C16—H16C109.5H20E—C200—H20F109.5
H16A—C16—H16C109.5C200—O200—H200109.5
H16B—C16—H16C109.5
C29—O1—C1—O23.6 (10)C12—C14—C15—C17178.7 (5)
C29—O1—C1—C2178.6 (5)O6—C14—C15—C1673.5 (6)
O2—C1—C2—C462.3 (9)C12—C14—C15—C1651.4 (7)
O1—C1—C2—C4119.9 (6)C14—C15—C17—C18156.6 (5)
O2—C1—C2—C361.0 (9)C16—C15—C17—C1875.7 (6)
O1—C1—C2—C3116.9 (6)C15—C17—C18—C19175.5 (5)
C1—C2—C4—O360.7 (6)C21—O7—C19—C18118.5 (6)
C3—C2—C4—O3176.5 (5)C21—O7—C19—C20119.3 (6)
C1—C2—C4—C5177.4 (5)C17—C18—C19—O764.8 (6)
C3—C2—C4—C554.6 (7)C17—C18—C19—C20175.6 (5)
O3—C4—C5—C664.8 (7)C19—O7—C21—O83.3 (9)
C2—C4—C5—C655.1 (7)C19—O7—C21—C22178.4 (5)
O3—C4—C5—C758.0 (7)O8—C21—C22—C2444.5 (8)
C2—C4—C5—C7177.9 (5)O7—C21—C22—C24137.2 (5)
C6—C5—C7—C874.5 (7)O8—C21—C22—C2380.1 (7)
C4—C5—C7—C8160.4 (5)O7—C21—C22—C2398.2 (6)
C5—C7—C8—C9175.0 (6)C21—C22—C24—O954.6 (6)
C11—O4—C9—C8149.7 (5)C23—C22—C24—O9177.6 (5)
C11—O4—C9—C1088.0 (6)C21—C22—C24—C25178.2 (5)
C7—C8—C9—O466.5 (7)C23—C22—C24—C2558.8 (7)
C7—C8—C9—C10173.8 (5)O9—C24—C25—C2665.7 (6)
C9—O4—C11—O510.5 (9)C22—C24—C25—C2654.9 (7)
C9—O4—C11—C12169.0 (5)O9—C24—C25—C2757.7 (7)
O5—C11—C12—C1350.9 (9)C22—C24—C25—C27178.3 (5)
O4—C11—C12—C13129.6 (5)C24—C25—C27—C28169.3 (5)
O5—C11—C12—C1469.5 (8)C26—C25—C27—C2866.8 (7)
O4—C11—C12—C14110.1 (5)C25—C27—C28—C29173.1 (5)
C11—C12—C14—O654.2 (6)C1—O1—C29—C28130.3 (5)
C13—C12—C14—O6174.7 (5)C1—O1—C29—C30109.3 (6)
C11—C12—C14—C15179.0 (5)C27—C28—C29—O161.0 (6)
C13—C12—C14—C1558.5 (7)C27—C28—C29—C30178.2 (5)
O6—C14—C15—C1753.8 (6)

Experimental details

Crystal data
Chemical formulaC30H54O9·2CH4O·H2O
Mr640.83
Crystal system, space groupOrthorhombic, P212121
Temperature (K)153
a, b, c (Å)8.8977 (14), 19.524 (3), 21.445 (3)
V3)3725.5 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.32 × 0.25 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.906, 0.953
No. of measured, independent and
observed [I > 2σ(I)] reflections
22975, 4594, 1359
Rint0.108
(sin θ/λ)max1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.085, 0.86
No. of reflections4594
No. of parameters413
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.17

Computer programs: SMART (Bruker, 2002), SMART, SAINT (Bruker, 2002), SHELXTL (Bruker, 2002), SHELXTL.

Selected geometric parameters (Å, º) top
O1—C11.330 (7)C4—C51.526 (7)
O1—C291.455 (6)C5—C61.508 (7)
O2—C11.203 (7)C5—C71.516 (7)
O3—C41.464 (5)C7—C81.503 (6)
C1—C21.502 (8)C8—C91.504 (7)
C2—C41.527 (6)C9—C101.523 (6)
C2—C31.528 (6)
C1—O1—C29117.2 (5)C2—C4—C5115.4 (5)
O2—C1—O1124.4 (7)C6—C5—C7109.3 (6)
O2—C1—C2122.7 (7)C6—C5—C4113.4 (5)
O1—C1—C2112.8 (6)C7—C5—C4110.1 (5)
C1—C2—C4108.8 (5)C8—C7—C5116.6 (5)
C1—C2—C3111.0 (5)C7—C8—C9113.3 (5)
C4—C2—C3111.7 (5)O4—C9—C8105.5 (5)
O3—C4—C2106.1 (5)O4—C9—C10109.4 (5)
O3—C4—C5109.8 (5)C8—C9—C10113.5 (5)
 

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