Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008055/bt6265sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008055/bt6265Isup2.hkl |
CCDC reference: 214609
Isolation of the compound has already been described by Suwarso et al. (1999). The product was crystallized from CH2Cl2/CH3OH solution.
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.
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.
C30H54O9·2CH4O·H2O | Dx = 1.143 Mg m−3 |
Mr = 640.83 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 713 reflections |
a = 8.8977 (14) Å | θ = 2.5–12.7° |
b = 19.524 (3) Å | µ = 0.09 mm−1 |
c = 21.445 (3) Å | T = 153 K |
V = 3725.5 (10) Å3 | Block, colourless |
Z = 4 | 0.32 × 0.25 × 0.15 mm |
F(000) = 1408 |
Bruker SMART CCD area-detector diffractometer | 4594 independent reflections |
Radiation source: sealed tube | 1359 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.108 |
π and ω scans | θmax = 27.1°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→8 |
Tmin = 0.906, Tmax = 0.953 | k = −24→24 |
22975 measured reflections | l = −27→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: geom and difmap |
wR(F2) = 0.085 | H-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 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C30H54O9·2CH4O·H2O | V = 3725.5 (10) Å3 |
Mr = 640.83 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.8977 (14) Å | µ = 0.09 mm−1 |
b = 19.524 (3) Å | T = 153 K |
c = 21.445 (3) Å | 0.32 × 0.25 × 0.15 mm |
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 = 0.953 | Rint = 0.108 |
22975 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 0.86 | Δρmax = 0.17 e Å−3 |
4594 reflections | Δρmin = −0.17 e Å−3 |
413 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.0931 (4) | 1.0277 (2) | −0.26806 (18) | 0.0401 (12) | |
O2 | −0.2940 (5) | 0.9607 (2) | −0.2519 (2) | 0.0675 (17) | |
O3 | −0.0506 (4) | 0.9515 (2) | −0.13037 (18) | 0.0447 (12) | |
H3 | −0.1309 | 0.9627 | −0.1124 | 0.067* | |
O4 | 0.1150 (4) | 0.7852 (2) | 0.04383 (19) | 0.0411 (12) | |
O5 | −0.0325 (5) | 0.7908 (2) | 0.12820 (19) | 0.0540 (14) | |
O6 | 0.0238 (5) | 0.9389 (2) | 0.05163 (18) | 0.0475 (12) | |
H6 | 0.0768 | 0.9658 | 0.0304 | 0.071* | |
O7 | 0.0170 (4) | 1.20544 (19) | 0.08711 (17) | 0.0359 (12) | |
O8 | −0.2215 (5) | 1.1860 (2) | 0.05796 (18) | 0.0504 (14) | |
O9 | −0.0623 (5) | 1.1075 (2) | −0.04613 (15) | 0.0453 (12) | |
H9 | 0.0033 | 1.0925 | −0.0708 | 0.068* | |
C1 | −0.1602 (8) | 0.9694 (4) | −0.2521 (3) | 0.044 (2) | |
C2 | −0.0505 (7) | 0.9135 (3) | −0.2364 (2) | 0.0375 (18) | |
H2A | 0.0535 | 0.9324 | −0.2396 | 0.045* | |
C3 | −0.0650 (7) | 0.8536 (3) | −0.2819 (2) | 0.057 (2) | |
H3A | −0.1627 | 0.8313 | −0.2761 | 0.086* | |
H3B | 0.0155 | 0.8205 | −0.2740 | 0.086* | |
H3C | −0.0570 | 0.8707 | −0.3248 | 0.086* | |
C4 | −0.0770 (7) | 0.8909 (3) | −0.1691 (2) | 0.0383 (18) | |
H4A | −0.1848 | 0.8771 | −0.1646 | 0.046* | |
C5 | 0.0213 (7) | 0.8318 (3) | −0.1466 (3) | 0.0374 (18) | |
H5A | −0.0048 | 0.7903 | −0.1717 | 0.045* | |
C6 | 0.1873 (7) | 0.8451 (3) | −0.1543 (3) | 0.060 (2) | |
H6A | 0.2154 | 0.8861 | −0.1307 | 0.089* | |
H6B | 0.2101 | 0.8522 | −0.1986 | 0.089* | |
H6C | 0.2442 | 0.8057 | −0.1387 | 0.089* | |
C7 | −0.0119 (7) | 0.8163 (3) | −0.0787 (2) | 0.047 (2) | |
H7A | 0.0387 | 0.8514 | −0.0528 | 0.056* | |
H7B | −0.1214 | 0.8213 | −0.0720 | 0.056* | |
C8 | 0.0347 (7) | 0.7469 (3) | −0.0553 (3) | 0.0459 (19) | |
H8A | 0.1425 | 0.7399 | −0.0647 | 0.055* | |
H8B | −0.0229 | 0.7114 | −0.0780 | 0.055* | |
C9 | 0.0102 (7) | 0.7377 (3) | 0.0136 (3) | 0.045 (2) | |
H9A | −0.0953 | 0.7507 | 0.0244 | 0.054* | |
C10 | 0.0412 (7) | 0.6651 (3) | 0.0362 (2) | 0.058 (2) | |
H10A | 0.1403 | 0.6504 | 0.0214 | 0.086* | |
H10B | −0.0359 | 0.6341 | 0.0199 | 0.086* | |
H10C | 0.0393 | 0.6641 | 0.0819 | 0.086* | |
C11 | 0.0740 (8) | 0.8112 (4) | 0.0988 (3) | 0.041 (2) | |
C12 | 0.1748 (7) | 0.8686 (3) | 0.1191 (3) | 0.0336 (17) | |
H12A | 0.2632 | 0.8715 | 0.0905 | 0.040* | |
C13 | 0.2289 (7) | 0.8572 (3) | 0.1855 (2) | 0.052 (2) | |
H13A | 0.1426 | 0.8575 | 0.2139 | 0.078* | |
H13B | 0.2987 | 0.8938 | 0.1972 | 0.078* | |
H13C | 0.2802 | 0.8129 | 0.1882 | 0.078* | |
C14 | 0.0838 (7) | 0.9346 (3) | 0.1150 (2) | 0.0375 (18) | |
H14A | −0.0047 | 0.9285 | 0.1432 | 0.045* | |
C15 | 0.1576 (7) | 1.0013 (3) | 0.1339 (2) | 0.0317 (17) | |
H15A | 0.1787 | 0.9978 | 0.1796 | 0.038* | |
C16 | 0.3102 (7) | 1.0128 (3) | 0.1015 (2) | 0.053 (2) | |
H16A | 0.2953 | 1.0152 | 0.0563 | 0.079* | |
H16B | 0.3779 | 0.9747 | 0.1114 | 0.079* | |
H16C | 0.3545 | 1.0558 | 0.1162 | 0.079* | |
C17 | 0.0538 (6) | 1.0610 (3) | 0.1256 (3) | 0.0393 (17) | |
H17A | −0.0496 | 1.0454 | 0.1349 | 0.047* | |
H17B | 0.0561 | 1.0745 | 0.0811 | 0.047* | |
C18 | 0.0857 (7) | 1.1245 (3) | 0.1648 (2) | 0.0384 (18) | |
H18A | 0.0747 | 1.1124 | 0.2094 | 0.046* | |
H18B | 0.1914 | 1.1385 | 0.1580 | 0.046* | |
C19 | −0.0144 (7) | 1.1841 (3) | 0.1508 (2) | 0.0428 (19) | |
H19 | −0.1218 | 1.1694 | 0.1541 | 0.051* | |
C20 | 0.0123 (7) | 1.2439 (3) | 0.1937 (2) | 0.054 (2) | |
H20A | 0.1147 | 1.2611 | 0.1877 | 0.081* | |
H20B | −0.0004 | 1.2291 | 0.2371 | 0.081* | |
H20C | −0.0600 | 1.2803 | 0.1843 | 0.081* | |
C21 | −0.0912 (8) | 1.2026 (3) | 0.0463 (3) | 0.0319 (17) | |
C22 | −0.0426 (7) | 1.2242 (3) | −0.0182 (2) | 0.0343 (17) | |
H22A | 0.0694 | 1.2207 | −0.0205 | 0.041* | |
C23 | −0.0862 (7) | 1.2989 (3) | −0.0300 (2) | 0.0463 (19) | |
H23A | −0.1959 | 1.3028 | −0.0321 | 0.069* | |
H23B | −0.0425 | 1.3142 | −0.0696 | 0.069* | |
H23C | −0.0482 | 1.3276 | 0.0040 | 0.069* | |
C24 | −0.1093 (7) | 1.1750 (3) | −0.0659 (2) | 0.0310 (17) | |
H24A | −0.2212 | 1.1773 | −0.0623 | 0.037* | |
C25 | −0.0681 (6) | 1.1876 (3) | −0.1342 (3) | 0.0367 (17) | |
H25A | −0.1100 | 1.2331 | −0.1467 | 0.044* | |
C26 | 0.1029 (6) | 1.1896 (3) | −0.1438 (2) | 0.049 (2) | |
H26A | 0.1476 | 1.1473 | −0.1276 | 0.074* | |
H26B | 0.1450 | 1.2290 | −0.1215 | 0.074* | |
H26C | 0.1251 | 1.1937 | −0.1884 | 0.074* | |
C27 | −0.1407 (7) | 1.1323 (3) | −0.1756 (2) | 0.0419 (19) | |
H27A | −0.0910 | 1.0880 | −0.1668 | 0.050* | |
H27B | −0.2476 | 1.1277 | −0.1634 | 0.050* | |
C28 | −0.1336 (7) | 1.1454 (3) | −0.2464 (2) | 0.0358 (18) | |
H28A | −0.1949 | 1.1862 | −0.2566 | 0.043* | |
H28B | −0.0284 | 1.1552 | −0.2585 | 0.043* | |
C29 | −0.1896 (7) | 1.0856 (3) | −0.2827 (3) | 0.0373 (18) | |
H29 | −0.2958 | 1.0752 | −0.2710 | 0.045* | |
C30 | −0.1781 (6) | 1.0975 (3) | −0.3525 (2) | 0.048 (2) | |
H30A | −0.0737 | 1.1079 | −0.3636 | 0.072* | |
H30B | −0.2425 | 1.1361 | −0.3643 | 0.072* | |
H30C | −0.2108 | 1.0563 | −0.3747 | 0.072* | |
C100 | −0.3127 (8) | 1.0062 (3) | 0.0032 (2) | 0.090 (3) | |
H10D | −0.2249 | 0.9848 | 0.0227 | 0.135* | |
H10E | −0.4023 | 0.9786 | 0.0118 | 0.135* | |
H10F | −0.3265 | 1.0523 | 0.0202 | 0.135* | |
O100 | −0.2907 (6) | 1.0102 (3) | −0.06082 (19) | 0.0747 (17) | |
H100 | −0.2108 | 1.0318 | −0.0682 | 0.112* | |
C200 | −0.5930 (10) | 1.0304 (4) | −0.1713 (3) | 0.118 (4) | |
H20D | −0.6963 | 1.0144 | −0.1776 | 0.177* | |
H20E | −0.5231 | 0.9991 | −0.1921 | 0.177* | |
H20F | −0.5820 | 1.0764 | −0.1889 | 0.177* | |
O200 | −0.5616 (7) | 1.0322 (4) | −0.1082 (2) | 0.123 (2) | |
H200 | −0.6361 | 1.0176 | −0.0882 | 0.185* | |
O300 | −0.8376 (4) | 1.0096 (2) | −0.05529 (16) | 0.0532 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.032 (3) | 0.041 (3) | 0.047 (3) | 0.001 (3) | 0.001 (3) | 0.003 (2) |
O2 | 0.035 (3) | 0.072 (4) | 0.095 (4) | −0.002 (3) | −0.016 (3) | 0.022 (3) |
O3 | 0.043 (3) | 0.051 (3) | 0.040 (3) | 0.015 (3) | 0.006 (3) | −0.009 (2) |
O4 | 0.030 (3) | 0.044 (3) | 0.049 (3) | −0.003 (2) | −0.003 (3) | 0.000 (3) |
O5 | 0.050 (3) | 0.048 (3) | 0.064 (3) | −0.014 (3) | 0.022 (3) | 0.006 (3) |
O6 | 0.047 (3) | 0.032 (3) | 0.063 (3) | −0.003 (2) | 0.004 (3) | 0.003 (2) |
O7 | 0.032 (3) | 0.047 (3) | 0.029 (2) | −0.010 (3) | −0.009 (2) | 0.002 (2) |
O8 | 0.041 (3) | 0.075 (4) | 0.035 (3) | −0.001 (3) | −0.001 (3) | −0.006 (3) |
O9 | 0.049 (3) | 0.058 (3) | 0.030 (3) | 0.012 (3) | 0.006 (3) | −0.002 (2) |
C1 | 0.034 (5) | 0.055 (6) | 0.043 (5) | 0.006 (5) | −0.002 (5) | −0.014 (4) |
C2 | 0.037 (5) | 0.037 (4) | 0.039 (4) | −0.002 (4) | −0.001 (4) | −0.012 (3) |
C3 | 0.075 (6) | 0.041 (5) | 0.055 (4) | −0.011 (4) | −0.006 (5) | −0.010 (4) |
C4 | 0.036 (5) | 0.046 (5) | 0.034 (4) | 0.001 (4) | −0.010 (4) | −0.013 (4) |
C5 | 0.038 (5) | 0.034 (4) | 0.041 (4) | 0.001 (4) | 0.008 (4) | −0.004 (4) |
C6 | 0.048 (5) | 0.061 (6) | 0.070 (5) | −0.001 (4) | 0.003 (5) | 0.010 (4) |
C7 | 0.038 (5) | 0.045 (5) | 0.058 (5) | 0.013 (4) | 0.002 (4) | −0.007 (4) |
C8 | 0.047 (5) | 0.036 (5) | 0.055 (5) | 0.013 (4) | −0.009 (4) | 0.000 (4) |
C9 | 0.032 (5) | 0.030 (5) | 0.073 (5) | −0.012 (4) | −0.019 (4) | 0.008 (4) |
C10 | 0.046 (5) | 0.049 (5) | 0.078 (5) | −0.001 (4) | −0.017 (5) | 0.001 (4) |
C11 | 0.049 (6) | 0.039 (5) | 0.036 (5) | 0.013 (5) | −0.011 (4) | 0.004 (4) |
C12 | 0.025 (4) | 0.041 (5) | 0.036 (4) | 0.004 (4) | 0.004 (4) | −0.002 (4) |
C13 | 0.058 (6) | 0.051 (5) | 0.046 (4) | 0.013 (4) | −0.006 (4) | 0.011 (4) |
C14 | 0.040 (5) | 0.051 (5) | 0.022 (4) | 0.004 (4) | −0.004 (4) | 0.006 (4) |
C15 | 0.038 (5) | 0.033 (4) | 0.023 (3) | −0.005 (4) | −0.005 (4) | −0.001 (4) |
C16 | 0.049 (5) | 0.049 (5) | 0.060 (5) | 0.002 (4) | 0.000 (4) | 0.001 (4) |
C17 | 0.032 (4) | 0.041 (4) | 0.045 (4) | 0.004 (4) | 0.002 (4) | 0.009 (4) |
C18 | 0.038 (5) | 0.050 (5) | 0.026 (4) | −0.007 (4) | −0.005 (4) | −0.011 (4) |
C19 | 0.040 (5) | 0.052 (5) | 0.036 (4) | 0.014 (4) | −0.005 (4) | 0.000 (4) |
C20 | 0.061 (5) | 0.048 (5) | 0.054 (5) | 0.003 (4) | −0.003 (4) | −0.016 (4) |
C21 | 0.041 (5) | 0.016 (4) | 0.039 (5) | −0.002 (4) | 0.002 (4) | −0.008 (4) |
C22 | 0.026 (4) | 0.036 (4) | 0.041 (4) | 0.003 (4) | 0.005 (4) | 0.003 (4) |
C23 | 0.051 (5) | 0.036 (4) | 0.052 (4) | 0.001 (4) | −0.001 (4) | −0.002 (4) |
C24 | 0.034 (4) | 0.021 (4) | 0.037 (4) | 0.008 (4) | −0.001 (4) | 0.002 (3) |
C25 | 0.033 (5) | 0.037 (5) | 0.040 (4) | 0.000 (4) | 0.012 (4) | 0.006 (4) |
C26 | 0.051 (5) | 0.060 (5) | 0.035 (4) | 0.003 (4) | 0.007 (4) | 0.000 (4) |
C27 | 0.039 (5) | 0.042 (5) | 0.045 (4) | −0.003 (4) | 0.000 (4) | −0.002 (4) |
C28 | 0.030 (4) | 0.041 (5) | 0.036 (4) | 0.005 (4) | −0.002 (4) | 0.003 (4) |
C29 | 0.036 (5) | 0.034 (5) | 0.043 (4) | 0.010 (4) | −0.002 (4) | −0.002 (4) |
C30 | 0.030 (4) | 0.070 (6) | 0.044 (4) | 0.008 (4) | 0.000 (4) | −0.004 (4) |
C100 | 0.140 (9) | 0.077 (6) | 0.053 (5) | −0.035 (7) | 0.013 (6) | 0.015 (5) |
O100 | 0.094 (5) | 0.064 (4) | 0.066 (3) | −0.019 (4) | 0.042 (3) | 0.001 (3) |
C200 | 0.116 (9) | 0.155 (9) | 0.083 (6) | 0.021 (8) | 0.010 (7) | −0.007 (7) |
O200 | 0.085 (5) | 0.215 (7) | 0.070 (4) | −0.023 (5) | −0.011 (4) | 0.003 (5) |
O300 | 0.042 (3) | 0.068 (3) | 0.050 (3) | 0.006 (3) | −0.005 (3) | 0.001 (3) |
O1—C1 | 1.330 (7) | C15—H15A | 1.0000 |
O1—C29 | 1.455 (6) | C16—H16A | 0.9800 |
O2—C1 | 1.203 (7) | C16—H16B | 0.9800 |
O3—C4 | 1.464 (5) | C16—H16C | 0.9800 |
O3—H3 | 0.8400 | C17—C18 | 1.526 (6) |
O4—C11 | 1.336 (6) | C17—H17A | 0.9900 |
O4—C9 | 1.467 (6) | C17—H17B | 0.9900 |
O5—C11 | 1.205 (7) | C18—C19 | 1.496 (7) |
O6—C14 | 1.462 (6) | C18—H18A | 0.9900 |
O6—H6 | 0.8400 | C18—H18B | 0.9900 |
O7—C21 | 1.303 (6) | C19—C20 | 1.504 (6) |
O7—C19 | 1.456 (5) | C19—H19 | 1.0000 |
O8—C21 | 1.230 (6) | C20—H20A | 0.9800 |
O9—C24 | 1.446 (5) | C20—H20B | 0.9800 |
O9—H9 | 0.8400 | C20—H20C | 0.9800 |
C1—C2 | 1.502 (8) | C21—C22 | 1.508 (7) |
C2—C4 | 1.527 (6) | C22—C24 | 1.525 (6) |
C2—C3 | 1.528 (6) | C22—C23 | 1.530 (6) |
C2—H2A | 1.0000 | C22—H22A | 1.0000 |
C3—H3A | 0.9800 | C23—H23A | 0.9800 |
C3—H3B | 0.9800 | C23—H23B | 0.9800 |
C3—H3C | 0.9800 | C23—H23C | 0.9800 |
C4—C5 | 1.526 (7) | C24—C25 | 1.528 (6) |
C4—H4A | 1.0000 | C24—H24A | 1.0000 |
C5—C6 | 1.508 (7) | C25—C26 | 1.536 (7) |
C5—C7 | 1.516 (7) | C25—C27 | 1.540 (7) |
C5—H5A | 1.0000 | C25—H25A | 1.0000 |
C6—H6A | 0.9800 | C26—H26A | 0.9800 |
C6—H6B | 0.9800 | C26—H26B | 0.9800 |
C6—H6C | 0.9800 | C26—H26C | 0.9800 |
C7—C8 | 1.503 (6) | C27—C28 | 1.540 (5) |
C7—H7A | 0.9900 | C27—H27A | 0.9900 |
C7—H7B | 0.9900 | C27—H27B | 0.9900 |
C8—C9 | 1.504 (7) | C28—C29 | 1.490 (6) |
C8—H8A | 0.9900 | C28—H28A | 0.9900 |
C8—H8B | 0.9900 | C28—H28B | 0.9900 |
C9—C10 | 1.523 (6) | C29—C30 | 1.518 (6) |
C9—H9A | 1.0000 | C29—H29 | 1.0000 |
C10—H10A | 0.9800 | C30—H30A | 0.9800 |
C10—H10B | 0.9800 | C30—H30B | 0.9800 |
C10—H10C | 0.9800 | C30—H30C | 0.9800 |
C11—C12 | 1.500 (8) | C100—O100 | 1.389 (5) |
C12—C13 | 1.519 (6) | C100—H10D | 0.9800 |
C12—C14 | 1.525 (7) | C100—H10E | 0.9800 |
C12—H12A | 1.0000 | C100—H10F | 0.9800 |
C13—H13A | 0.9800 | O100—H100 | 0.8400 |
C13—H13B | 0.9800 | C200—O200 | 1.382 (6) |
C13—H13C | 0.9800 | C200—H20D | 0.9800 |
C14—C15 | 1.512 (7) | C200—H20E | 0.9800 |
C14—H14A | 1.0000 | C200—H20F | 0.9800 |
C15—C17 | 1.497 (7) | O200—H200 | 0.8400 |
C15—C16 | 1.542 (6) | ||
C1—O1—C29 | 117.2 (5) | C15—C17—C18 | 116.9 (5) |
C4—O3—H3 | 109.5 | C15—C17—H17A | 108.1 |
C11—O4—C9 | 117.2 (5) | C18—C17—H17A | 108.1 |
C14—O6—H6 | 109.5 | C15—C17—H17B | 108.1 |
C21—O7—C19 | 118.5 (5) | C18—C17—H17B | 108.1 |
C24—O9—H9 | 109.5 | H17A—C17—H17B | 107.3 |
O2—C1—O1 | 124.4 (7) | C19—C18—C17 | 114.3 (5) |
O2—C1—C2 | 122.7 (7) | C19—C18—H18A | 108.7 |
O1—C1—C2 | 112.8 (6) | C17—C18—H18A | 108.7 |
C1—C2—C4 | 108.8 (5) | C19—C18—H18B | 108.7 |
C1—C2—C3 | 111.0 (5) | C17—C18—H18B | 108.7 |
C4—C2—C3 | 111.7 (5) | H18A—C18—H18B | 107.6 |
C1—C2—H2A | 108.4 | O7—C19—C18 | 107.2 (5) |
C4—C2—H2A | 108.4 | O7—C19—C20 | 108.8 (5) |
C3—C2—H2A | 108.4 | C18—C19—C20 | 112.8 (5) |
C2—C3—H3A | 109.5 | O7—C19—H19 | 109.4 |
C2—C3—H3B | 109.5 | C18—C19—H19 | 109.4 |
H3A—C3—H3B | 109.5 | C20—C19—H19 | 109.4 |
C2—C3—H3C | 109.5 | C19—C20—H20A | 109.5 |
H3A—C3—H3C | 109.5 | C19—C20—H20B | 109.5 |
H3B—C3—H3C | 109.5 | H20A—C20—H20B | 109.5 |
O3—C4—C2 | 106.1 (5) | C19—C20—H20C | 109.5 |
O3—C4—C5 | 109.8 (5) | H20A—C20—H20C | 109.5 |
C2—C4—C5 | 115.4 (5) | H20B—C20—H20C | 109.5 |
O3—C4—H4A | 108.4 | O8—C21—O7 | 124.8 (6) |
C2—C4—H4A | 108.4 | O8—C21—C22 | 122.1 (6) |
C5—C4—H4A | 108.4 | O7—C21—C22 | 113.1 (6) |
C6—C5—C7 | 109.3 (6) | C21—C22—C24 | 109.1 (5) |
C6—C5—C4 | 113.4 (5) | C21—C22—C23 | 110.2 (5) |
C7—C5—C4 | 110.1 (5) | C24—C22—C23 | 113.0 (5) |
C6—C5—H5A | 108.0 | C21—C22—H22A | 108.1 |
C7—C5—H5A | 108.0 | C24—C22—H22A | 108.1 |
C4—C5—H5A | 108.0 | C23—C22—H22A | 108.1 |
C5—C6—H6A | 109.5 | C22—C23—H23A | 109.5 |
C5—C6—H6B | 109.5 | C22—C23—H23B | 109.5 |
H6A—C6—H6B | 109.5 | H23A—C23—H23B | 109.5 |
C5—C6—H6C | 109.5 | C22—C23—H23C | 109.5 |
H6A—C6—H6C | 109.5 | H23A—C23—H23C | 109.5 |
H6B—C6—H6C | 109.5 | H23B—C23—H23C | 109.5 |
C8—C7—C5 | 116.6 (5) | O9—C24—C22 | 105.3 (4) |
C8—C7—H7A | 108.1 | O9—C24—C25 | 111.0 (5) |
C5—C7—H7A | 108.1 | C22—C24—C25 | 116.7 (5) |
C8—C7—H7B | 108.1 | O9—C24—H24A | 107.8 |
C5—C7—H7B | 108.1 | C22—C24—H24A | 107.8 |
H7A—C7—H7B | 107.3 | C25—C24—H24A | 107.8 |
C7—C8—C9 | 113.3 (5) | C24—C25—C26 | 111.7 (5) |
C7—C8—H8A | 108.9 | C24—C25—C27 | 109.9 (5) |
C9—C8—H8A | 108.9 | C26—C25—C27 | 110.8 (5) |
C7—C8—H8B | 108.9 | C24—C25—H25A | 108.1 |
C9—C8—H8B | 108.9 | C26—C25—H25A | 108.1 |
H8A—C8—H8B | 107.7 | C27—C25—H25A | 108.1 |
O4—C9—C8 | 105.5 (5) | C25—C26—H26A | 109.5 |
O4—C9—C10 | 109.4 (5) | C25—C26—H26B | 109.5 |
C8—C9—C10 | 113.5 (5) | H26A—C26—H26B | 109.5 |
O4—C9—H9A | 109.5 | C25—C26—H26C | 109.5 |
C8—C9—H9A | 109.5 | H26A—C26—H26C | 109.5 |
C10—C9—H9A | 109.5 | H26B—C26—H26C | 109.5 |
C9—C10—H10A | 109.5 | C28—C27—C25 | 115.8 (5) |
C9—C10—H10B | 109.5 | C28—C27—H27A | 108.3 |
H10A—C10—H10B | 109.5 | C25—C27—H27A | 108.3 |
C9—C10—H10C | 109.5 | C28—C27—H27B | 108.3 |
H10A—C10—H10C | 109.5 | C25—C27—H27B | 108.3 |
H10B—C10—H10C | 109.5 | H27A—C27—H27B | 107.4 |
O5—C11—O4 | 123.4 (7) | C29—C28—C27 | 111.8 (5) |
O5—C11—C12 | 124.4 (6) | C29—C28—H28A | 109.3 |
O4—C11—C12 | 112.1 (6) | C27—C28—H28A | 109.3 |
C11—C12—C13 | 110.6 (5) | C29—C28—H28B | 109.3 |
C11—C12—C14 | 107.3 (5) | C27—C28—H28B | 109.3 |
C13—C12—C14 | 110.3 (5) | H28A—C28—H28B | 107.9 |
C11—C12—H12A | 109.5 | O1—C29—C28 | 107.4 (5) |
C13—C12—H12A | 109.5 | O1—C29—C30 | 107.0 (5) |
C14—C12—H12A | 109.5 | C28—C29—C30 | 112.0 (5) |
C12—C13—H13A | 109.5 | O1—C29—H29 | 110.1 |
C12—C13—H13B | 109.5 | C28—C29—H29 | 110.1 |
H13A—C13—H13B | 109.5 | C30—C29—H29 | 110.1 |
C12—C13—H13C | 109.5 | C29—C30—H30A | 109.5 |
H13A—C13—H13C | 109.5 | C29—C30—H30B | 109.5 |
H13B—C13—H13C | 109.5 | H30A—C30—H30B | 109.5 |
O6—C14—C15 | 111.0 (5) | C29—C30—H30C | 109.5 |
O6—C14—C12 | 107.2 (5) | H30A—C30—H30C | 109.5 |
C15—C14—C12 | 118.8 (5) | H30B—C30—H30C | 109.5 |
O6—C14—H14A | 106.4 | O100—C100—H10D | 109.5 |
C15—C14—H14A | 106.4 | O100—C100—H10E | 109.5 |
C12—C14—H14A | 106.4 | H10D—C100—H10E | 109.5 |
C17—C15—C14 | 111.7 (5) | O100—C100—H10F | 109.5 |
C17—C15—C16 | 112.1 (5) | H10D—C100—H10F | 109.5 |
C14—C15—C16 | 112.7 (5) | H10E—C100—H10F | 109.5 |
C17—C15—H15A | 106.6 | C100—O100—H100 | 109.5 |
C14—C15—H15A | 106.6 | O200—C200—H20D | 109.5 |
C16—C15—H15A | 106.6 | O200—C200—H20E | 109.5 |
C15—C16—H16A | 109.5 | H20D—C200—H20E | 109.5 |
C15—C16—H16B | 109.5 | O200—C200—H20F | 109.5 |
H16A—C16—H16B | 109.5 | H20D—C200—H20F | 109.5 |
C15—C16—H16C | 109.5 | H20E—C200—H20F | 109.5 |
H16A—C16—H16C | 109.5 | C200—O200—H200 | 109.5 |
H16B—C16—H16C | 109.5 | ||
C29—O1—C1—O2 | 3.6 (10) | C12—C14—C15—C17 | 178.7 (5) |
C29—O1—C1—C2 | −178.6 (5) | O6—C14—C15—C16 | −73.5 (6) |
O2—C1—C2—C4 | −62.3 (9) | C12—C14—C15—C16 | 51.4 (7) |
O1—C1—C2—C4 | 119.9 (6) | C14—C15—C17—C18 | 156.6 (5) |
O2—C1—C2—C3 | 61.0 (9) | C16—C15—C17—C18 | −75.7 (6) |
O1—C1—C2—C3 | −116.9 (6) | C15—C17—C18—C19 | 175.5 (5) |
C1—C2—C4—O3 | −60.7 (6) | C21—O7—C19—C18 | 118.5 (6) |
C3—C2—C4—O3 | 176.5 (5) | C21—O7—C19—C20 | −119.3 (6) |
C1—C2—C4—C5 | 177.4 (5) | C17—C18—C19—O7 | −64.8 (6) |
C3—C2—C4—C5 | 54.6 (7) | C17—C18—C19—C20 | 175.6 (5) |
O3—C4—C5—C6 | −64.8 (7) | C19—O7—C21—O8 | 3.3 (9) |
C2—C4—C5—C6 | 55.1 (7) | C19—O7—C21—C22 | −178.4 (5) |
O3—C4—C5—C7 | 58.0 (7) | O8—C21—C22—C24 | −44.5 (8) |
C2—C4—C5—C7 | 177.9 (5) | O7—C21—C22—C24 | 137.2 (5) |
C6—C5—C7—C8 | −74.5 (7) | O8—C21—C22—C23 | 80.1 (7) |
C4—C5—C7—C8 | 160.4 (5) | O7—C21—C22—C23 | −98.2 (6) |
C5—C7—C8—C9 | 175.0 (6) | C21—C22—C24—O9 | −54.6 (6) |
C11—O4—C9—C8 | 149.7 (5) | C23—C22—C24—O9 | −177.6 (5) |
C11—O4—C9—C10 | −88.0 (6) | C21—C22—C24—C25 | −178.2 (5) |
C7—C8—C9—O4 | −66.5 (7) | C23—C22—C24—C25 | 58.8 (7) |
C7—C8—C9—C10 | 173.8 (5) | O9—C24—C25—C26 | −65.7 (6) |
C9—O4—C11—O5 | 10.5 (9) | C22—C24—C25—C26 | 54.9 (7) |
C9—O4—C11—C12 | −169.0 (5) | O9—C24—C25—C27 | 57.7 (7) |
O5—C11—C12—C13 | 50.9 (9) | C22—C24—C25—C27 | 178.3 (5) |
O4—C11—C12—C13 | −129.6 (5) | C24—C25—C27—C28 | 169.3 (5) |
O5—C11—C12—C14 | −69.5 (8) | C26—C25—C27—C28 | −66.8 (7) |
O4—C11—C12—C14 | 110.1 (5) | C25—C27—C28—C29 | 173.1 (5) |
C11—C12—C14—O6 | −54.2 (6) | C1—O1—C29—C28 | 130.3 (5) |
C13—C12—C14—O6 | −174.7 (5) | C1—O1—C29—C30 | −109.3 (6) |
C11—C12—C14—C15 | 179.0 (5) | C27—C28—C29—O1 | −61.0 (6) |
C13—C12—C14—C15 | 58.5 (7) | C27—C28—C29—C30 | −178.2 (5) |
O6—C14—C15—C17 | 53.8 (6) |
Experimental details
Crystal data | |
Chemical formula | C30H54O9·2CH4O·H2O |
Mr | 640.83 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 153 |
a, b, c (Å) | 8.8977 (14), 19.524 (3), 21.445 (3) |
V (Å3) | 3725.5 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.32 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.906, 0.953 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22975, 4594, 1359 |
Rint | 0.108 |
(sin θ/λ)max (Å−1) | 0.641 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.085, 0.86 |
No. of reflections | 4594 |
No. of parameters | 413 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.17 |
Computer programs: SMART (Bruker, 2002), SMART, SAINT (Bruker, 2002), SHELXTL (Bruker, 2002), SHELXTL.
O1—C1 | 1.330 (7) | C4—C5 | 1.526 (7) |
O1—C29 | 1.455 (6) | C5—C6 | 1.508 (7) |
O2—C1 | 1.203 (7) | C5—C7 | 1.516 (7) |
O3—C4 | 1.464 (5) | C7—C8 | 1.503 (6) |
C1—C2 | 1.502 (8) | C8—C9 | 1.504 (7) |
C2—C4 | 1.527 (6) | C9—C10 | 1.523 (6) |
C2—C3 | 1.528 (6) | ||
C1—O1—C29 | 117.2 (5) | C2—C4—C5 | 115.4 (5) |
O2—C1—O1 | 124.4 (7) | C6—C5—C7 | 109.3 (6) |
O2—C1—C2 | 122.7 (7) | C6—C5—C4 | 113.4 (5) |
O1—C1—C2 | 112.8 (6) | C7—C5—C4 | 110.1 (5) |
C1—C2—C4 | 108.8 (5) | C8—C7—C5 | 116.6 (5) |
C1—C2—C3 | 111.0 (5) | C7—C8—C9 | 113.3 (5) |
C4—C2—C3 | 111.7 (5) | O4—C9—C8 | 105.5 (5) |
O3—C4—C2 | 106.1 (5) | O4—C9—C10 | 109.4 (5) |
O3—C4—C5 | 109.8 (5) | C8—C9—C10 | 113.5 (5) |
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).