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The structure of the crown ether 1,8-(3,6,9-trioxaundecane-1,11-diyldioxy)-9,10-dihydro-10,10-dimethylanthracene-9-ol, C24H30O6·H2O (1), code name P326, the parent compound for a series of derivatives, has been determined by both X-ray diffraction at room temperature and neutron diffraction at very low temperature. The unit cells are very similar at both temperatures and in both cases the crystals exhibit P21 symmetry with Z = 4 (two molecules, A and B, respectively, per asymmetric unit) and pseudosymmetry P21/c. The higher symmetry is broken mainly by the two independent water molecules in the unit cell, some reflections which would be absent in P21/c having strong intensities in both the X-ray and neutron data. In both molecules A and B hydrogen bonds involving the water molecule stabilize the macrocyclic ring structure, one involving the macrocyclic O(9) as a donor. Close contacts between the water and macrocyclic O atoms in each molecule also suggest the presence of two bifurcated hydrogen bonds, involving water HW2 to both O(16) and O(18), and water HW1 to both O(18) and O(20), respectively, with considerable variation in the geometry being present. Both molecules A and B exhibit very close pseudosymmetry across a plane perpendicular to the molecular plane and through atoms C(9) and O(18), and in addition are predominantly planar structures. The X-ray analysis failed to reveal one H atom per water molecule, each being subsequently included after location and refinement in the neutron analysis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100015184/an0566sup1.cif
Contains datablocks xray, neutron, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100015184/an0566xraysup2.hkl
Contains datablock s92

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100015184/an0566neutronsup3.hkl
Contains datablock s92

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768100015184/an0566sup4.pdf
Supplementary material

CCDC references: 166505; 166506

Computing details top

Data collection: CAD-4 EXPRESS88 for xray; RETREAT for neutron. Program(s) used to solve structure: SHELXS86 (Sheldrick, 1990) for xray; SHELXS86? (Sheldrick, 1990) for neutron. Program(s) used to refine structure: SHELXL92 (Sheldrick, 1993) for xray; SHELXL92? (Sheldrick, 1993) for neutron. Molecular graphics: SNOOPI for neutron.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
(xray) top
Crystal data top
C24H30O6·H2OF(000) = 928
Mr = 432.50Dx = 1.258 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2y1Cell parameters from 25 reflections
a = 12.845 (5) Åθ = 25–30°
b = 14.575 (3) ŵ = 0.75 mm1
c = 13.779 (2) ÅT = 293 K
β = 117.72 (2)°Plate, colourless
V = 2283.6 (11) Å30.35 × 0.25 × 0.20 mm
Z = 4
Data collection top
Nonius CAD-4
diffractometer
4804 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 72.9°, θmin = 3.6°
ω/2θ scansh = 1515
17753 measured reflectionsk = 1818
9092 independent reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062Calculated w = 1/[σ2(Fo2) + (0.0922P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.169(Δ/σ)max = 0.078
S = 0.91Δρmax = 0.23 e Å3
9092 reflectionsΔρmin = 0.26 e Å3
605 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
217 restraintsAbsolute structure parameter: 0.2 (4)
Primary atom site location: structure-invariant direct methods
Crystal data top
C24H30O6·H2OV = 2283.6 (11) Å3
Mr = 432.50Z = 4
Monoclinic, P21Cu Kα radiation
a = 12.845 (5) ŵ = 0.75 mm1
b = 14.575 (3) ÅT = 293 K
c = 13.779 (2) Å0.35 × 0.25 × 0.20 mm
β = 117.72 (2)°
Data collection top
Nonius CAD-4
diffractometer
4804 reflections with I > 2σ(I)
17753 measured reflectionsRint = 0.046
9092 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.062217 restraints
wR(F2) = 0.169Δρmax = 0.23 e Å3
S = 0.91Δρmin = 0.26 e Å3
9092 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
605 parametersAbsolute structure parameter: 0.2 (4)
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
O20A1.26721 (14)1.28501 (15)0.26123 (15)0.0892 (8)
C21A1.1736 (2)1.3377 (2)0.2564 (2)0.0919 (12)
H21A1.2025 (2)1.3968 (2)0.2910 (2)0.128 (9)*
H21B1.1374 (2)1.3067 (2)0.2954 (2)0.128 (9)*
C10A0.6746 (2)1.0963 (2)0.1405 (2)0.0625 (8)
C23A0.6729 (3)1.0505 (2)0.2406 (2)0.0876 (11)
H23A0.6383 (13)0.9906 (5)0.2501 (8)0.092 (6)*
H23B0.7518 (3)1.0449 (10)0.2303 (6)0.092 (6)*
H23C0.6273 (12)1.0870 (6)0.3045 (3)0.092 (6)*
C24A0.5486 (3)1.1187 (2)0.1648 (3)0.1043 (14)
H24A0.5473 (4)1.1353 (14)0.0980 (4)0.124 (7)*
H24B0.4996 (5)1.0659 (5)0.1961 (16)0.124 (7)*
H24C0.5197 (7)1.1689 (10)0.2156 (14)0.124 (7)*
C14A0.7499 (2)1.1809 (2)0.1093 (2)0.0636 (8)
C4A0.7084 (3)1.2545 (2)0.1814 (2)0.0897 (12)
H4A0.6356 (3)1.2506 (2)0.2434 (2)0.103 (10)*
C3A0.7747 (2)1.3332 (2)0.1616 (2)0.0846 (11)
H3A0.7463 (2)1.3815 (2)0.2113 (2)0.077 (8)*
C2A0.8824 (2)1.3418 (2)0.0695 (2)0.0705 (8)
H2A0.9256 (2)1.3957 (2)0.0562 (2)0.039 (5)*
C1A0.9248 (2)1.2690 (2)0.0025 (2)0.0634 (8)
C13A0.8596 (2)1.1871 (2)0.0192 (2)0.0625 (8)
C9A0.9154 (2)1.1054 (2)0.0543 (2)0.0588 (7)
H9A0.9569 (2)1.1260 (2)0.1307 (2)0.087 (9)*
O9A0.9972 (2)1.06641 (13)0.02441 (14)0.0698 (6)
H9A11.0642 (2)1.0783 (14)0.0715 (10)0.065 (7)*
C12A0.8338 (2)1.0332 (2)0.0445 (2)0.0644 (9)
C8A0.8687 (2)0.9626 (2)0.1222 (2)0.0760 (10)
C7A0.8041 (2)0.8866 (2)0.1143 (2)0.0926 (12)
H7A0.8319 (2)0.8423 (2)0.1691 (2)0.095 (10)*
C6A0.6964 (3)0.8767 (2)0.0229 (2)0.1072 (15)
H6A0.6500 (3)0.8252 (2)0.0139 (2)0.069 (7)*
C5A0.6594 (3)0.9457 (2)0.0548 (2)0.1020 (14)
H5A0.5862 (3)0.9395 (2)0.1160 (2)0.168 (16)*
C11A0.7251 (2)1.0238 (2)0.0468 (2)0.0772 (9)
O8A0.9745 (2)0.98222 (13)0.2110 (2)0.0821 (6)
C15A1.0246 (2)0.9196 (2)0.3019 (2)0.0871 (11)
H15A1.0462 (2)0.8631 (2)0.2786 (2)0.267 (19)*
H15B0.9664 (2)0.9050 (2)0.3258 (2)0.267 (19)*
C16A1.1301 (2)0.9595 (2)0.3950 (2)0.0845 (11)
H16A1.1122 (2)1.0208 (2)0.4102 (2)0.126 (9)*
H16B1.1518 (2)0.9224 (2)0.4600 (2)0.126 (9)*
O16A1.22518 (14)0.9633 (2)0.37032 (14)0.0858 (7)
C17A1.3310 (2)0.9833 (2)0.4651 (2)0.0993 (13)
H17A1.3963 (2)0.9684 (2)0.4508 (2)0.135 (9)*
H17B1.3368 (2)0.9438 (2)0.5241 (2)0.135 (9)*
C18A1.3439 (3)1.0807 (2)0.5031 (2)0.1015 (14)
H18A1.2781 (3)1.0976 (2)0.5157 (2)0.194 (15)*
H18B1.4157 (3)1.0877 (2)0.5715 (2)0.194 (15)*
O18A1.3473 (2)1.13845 (13)0.4223 (2)0.0935 (8)
C19A1.3602 (4)1.2315 (2)0.4528 (3)0.122 (2)
H19A1.4308 (4)1.2401 (2)0.5218 (3)0.083 (6)*
H19B1.2932 (4)1.2518 (2)0.4616 (3)0.083 (6)*
C20A1.3682 (3)1.2850 (3)0.3652 (2)0.1063 (14)
H20A1.3864 (3)1.3480 (3)0.3898 (2)0.160 (12)*
H20B1.4338 (3)1.2614 (3)0.3562 (2)0.160 (12)*
C22A1.0854 (2)1.3511 (2)0.1398 (2)0.0818 (11)
H22A1.0289 (2)1.3975 (2)0.1346 (2)0.086 (7)*
H22B1.1244 (2)1.3719 (2)0.0980 (2)0.086 (7)*
O1A1.0270 (2)1.26735 (11)0.0965 (2)0.0795 (7)
OWA1.2217 (2)1.0887 (2)0.1896 (2)0.1034 (9)
HWA11.22531.05570.26260.050*
O20B1.22322 (15)1.1070 (2)0.87323 (14)0.0851 (7)
C21B1.1266 (2)1.1159 (3)0.8959 (2)0.0930 (12)
H21C1.1491 (2)1.1553 (3)0.9593 (2)0.093 (6)*
H21D1.1076 (2)1.0560 (3)0.9141 (2)0.093 (6)*
C10B0.6738 (3)0.9797 (2)0.3641 (3)0.0773 (10)
C23B0.6749 (3)1.0198 (2)0.2608 (3)0.0972 (14)
H23D0.7523 (5)1.0422 (11)0.2795 (4)0.092 (5)*
H23E0.6196 (12)1.0694 (8)0.2327 (9)0.092 (5)*
H23F0.6536 (15)0.9729 (4)0.2060 (6)0.092 (5)*
C24B0.5464 (2)0.9498 (3)0.3353 (3)0.0946 (13)
H24D0.5181 (8)0.9072 (12)0.2753 (13)0.120 (6)*
H24E0.4962 (5)1.0027 (3)0.3149 (18)0.120 (6)*
H24F0.5464 (4)0.9210 (14)0.3980 (7)0.120 (6)*
C14B0.7177 (2)1.0482 (2)0.4549 (2)0.0638 (9)
C4B0.6495 (2)1.1250 (2)0.4450 (3)0.0916 (12)
H4B0.5752 (2)1.1324 (2)0.3858 (3)0.077 (8)*
C3B0.6967 (3)1.1899 (2)0.5267 (2)0.1023 (14)
H3B0.6536 (3)1.2431 (2)0.5186 (2)0.202 (19)*
C2B0.8028 (2)1.1817 (2)0.6193 (2)0.0878 (12)
H2B0.8286 (2)1.2271 (2)0.6729 (2)0.096 (9)*
C1B0.8708 (2)1.1048 (2)0.6314 (2)0.0667 (8)
C13B0.8273 (2)1.0391 (2)0.5451 (2)0.0621 (8)
C9B0.9127 (2)0.9632 (2)0.5548 (2)0.0571 (8)
H9B0.9525 (2)0.9414 (2)0.6308 (2)0.044 (6)*
O9B1.0000 (2)1.00306 (14)0.5267 (2)0.0715 (6)
H9B11.063 (3)1.010 (7)0.5826 (11)0.49 (6)*
C12B0.8559 (2)0.8842 (2)0.4808 (2)0.0569 (8)
C8B0.9201 (2)0.8019 (2)0.5029 (2)0.0633 (9)
C7B0.8799 (2)0.7268 (2)0.4360 (2)0.0777 (10)
H7B0.9230 (2)0.6726 (2)0.4534 (2)0.156 (14)*
C6B0.7737 (2)0.7336 (2)0.3423 (2)0.0765 (9)
H6B0.7462 (2)0.6844 (2)0.2939 (2)0.092 (9)*
C5B0.7082 (2)0.81269 (15)0.3200 (2)0.0667 (9)
H5B0.6355 (2)0.81508 (15)0.2577 (2)0.078 (9)*
C11B0.7476 (2)0.8895 (2)0.3882 (2)0.0665 (9)
O8B1.0261 (2)0.80219 (14)0.5980 (2)0.0759 (7)
C15B1.0855 (3)0.7176 (2)0.6420 (2)0.0864 (12)
H15C1.1248 (3)0.6966 (2)0.6007 (2)0.122 (9)*
H15D1.0295 (3)0.6711 (2)0.6378 (2)0.122 (9)*
C16B1.1724 (2)0.7340 (2)0.7576 (2)0.0801 (10)
H16C1.1344 (2)0.7651 (2)0.7950 (2)0.073 (5)*
H16D1.2021 (2)0.6757 (2)0.7939 (2)0.073 (5)*
O16B1.2668 (2)0.7879 (2)0.7646 (2)0.0932 (8)
C17B1.3691 (3)0.7837 (3)0.8685 (2)0.109 (2)
H17C1.4362 (3)0.8046 (3)0.8601 (2)0.104 (7)*
H17D1.3833 (3)0.7202 (3)0.8924 (2)0.104 (7)*
C18B1.3609 (3)0.8397 (2)0.9554 (3)0.0924 (13)
H18C1.2937 (3)0.8200 (2)0.9642 (3)0.191 (13)*
H18D1.4312 (3)0.8310 (2)1.0247 (3)0.191 (13)*
O18B1.3487 (2)0.93327 (15)0.9260 (2)0.0989 (9)
C19B1.3442 (3)0.9910 (3)1.0066 (2)0.1053 (14)
H19C1.4158 (3)0.9845 (3)1.0753 (2)0.089 (6)*
H19D1.2781 (3)0.9741 (3)1.0187 (2)0.089 (6)*
C20B1.3312 (2)1.0877 (3)0.9673 (3)0.1019 (14)
H20C1.3387 (2)1.1281 (3)1.0262 (3)0.117 (9)*
H20D1.3951 (2)1.1018 (3)0.9509 (3)0.117 (9)*
C22B1.0205 (3)1.1545 (2)0.8024 (2)0.0891 (12)
H22C0.9615 (3)1.1694 (2)0.8251 (2)0.069 (5)*
H22D1.0405 (3)1.2100 (2)0.7760 (2)0.069 (5)*
O1B0.9771 (2)1.08707 (14)0.7189 (2)0.0767 (7)
OWB1.2241 (2)0.9817 (2)0.6897 (2)0.1035 (10)
HWB11.25121.01820.77440.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20A0.0800 (11)0.105 (2)0.0771 (11)0.0029 (12)0.0315 (10)0.0112 (11)
C21A0.072 (2)0.083 (2)0.098 (2)0.000 (2)0.020 (2)0.006 (2)
C10A0.0671 (13)0.072 (2)0.0450 (11)0.0204 (13)0.0233 (11)0.0127 (12)
C23A0.117 (2)0.089 (2)0.0533 (14)0.009 (2)0.0372 (15)0.0170 (15)
C24A0.111 (2)0.088 (2)0.101 (2)0.009 (2)0.038 (2)0.022 (2)
C14A0.0824 (14)0.057 (2)0.0594 (13)0.0075 (13)0.0397 (12)0.0061 (12)
C4A0.103 (2)0.073 (2)0.061 (2)0.008 (2)0.011 (2)0.003 (2)
C3A0.106 (2)0.085 (2)0.0433 (13)0.037 (2)0.0189 (14)0.0174 (14)
C2A0.096 (2)0.049 (2)0.0796 (15)0.0042 (15)0.0524 (13)0.0071 (13)
C1A0.0769 (14)0.058 (2)0.0649 (13)0.0009 (13)0.0406 (12)0.0101 (12)
C13A0.0737 (14)0.067 (2)0.0503 (13)0.0158 (14)0.0312 (12)0.0077 (12)
C9A0.0655 (12)0.062 (2)0.0570 (12)0.0192 (12)0.0352 (11)0.0039 (11)
O9A0.0707 (9)0.0763 (13)0.0658 (10)0.0039 (10)0.0346 (9)0.0030 (9)
C12A0.0674 (15)0.066 (2)0.0492 (13)0.0120 (14)0.0184 (12)0.0018 (12)
C8A0.0581 (14)0.094 (2)0.0605 (15)0.002 (2)0.0150 (12)0.007 (2)
C7A0.097 (2)0.069 (2)0.104 (2)0.003 (2)0.041 (2)0.017 (2)
C6A0.105 (2)0.070 (2)0.124 (3)0.024 (2)0.034 (2)0.023 (2)
C5A0.087 (2)0.119 (3)0.082 (2)0.010 (2)0.024 (2)0.006 (2)
C11A0.101 (2)0.058 (2)0.099 (2)0.0121 (15)0.0684 (14)0.0031 (13)
O8A0.1054 (12)0.0721 (13)0.0806 (10)0.0076 (11)0.0532 (10)0.0273 (10)
C15A0.114 (2)0.081 (2)0.078 (2)0.012 (2)0.055 (2)0.028 (2)
C16A0.110 (2)0.099 (2)0.0403 (12)0.024 (2)0.0321 (13)0.0145 (14)
O16A0.0923 (11)0.105 (2)0.0683 (10)0.0249 (12)0.0447 (9)0.0005 (11)
C17A0.096 (2)0.122 (3)0.064 (2)0.009 (2)0.024 (2)0.016 (2)
C18A0.100 (2)0.114 (3)0.053 (2)0.013 (2)0.004 (2)0.008 (2)
O18A0.1085 (13)0.109 (2)0.0638 (11)0.0072 (14)0.0409 (10)0.0049 (12)
C19A0.119 (3)0.111 (3)0.079 (2)0.001 (3)0.001 (2)0.018 (2)
C20A0.088 (2)0.124 (3)0.084 (2)0.036 (2)0.021 (2)0.011 (2)
C22A0.076 (2)0.076 (2)0.088 (2)0.001 (2)0.034 (2)0.019 (2)
O1A0.0791 (11)0.0452 (11)0.0969 (14)0.0051 (10)0.0265 (11)0.0014 (10)
OWA0.1239 (15)0.125 (2)0.0685 (11)0.0209 (14)0.0512 (11)0.0019 (13)
O20B0.0924 (12)0.112 (2)0.0576 (10)0.0031 (13)0.0403 (10)0.0046 (11)
C21B0.093 (2)0.124 (3)0.088 (2)0.013 (2)0.064 (2)0.020 (2)
C10B0.077 (2)0.066 (2)0.083 (2)0.018 (2)0.032 (2)0.026 (2)
C23B0.108 (2)0.078 (2)0.090 (2)0.024 (2)0.032 (2)0.005 (2)
C24B0.054 (2)0.105 (3)0.110 (3)0.003 (2)0.025 (2)0.021 (2)
C14B0.0588 (15)0.067 (2)0.0488 (14)0.0030 (14)0.0109 (13)0.0000 (13)
C4B0.083 (2)0.064 (2)0.109 (3)0.041 (2)0.029 (2)0.005 (2)
C3B0.100 (2)0.093 (3)0.115 (3)0.027 (2)0.051 (2)0.007 (2)
C2B0.099 (2)0.079 (2)0.092 (2)0.018 (2)0.049 (2)0.023 (2)
C1B0.104 (2)0.0457 (15)0.0698 (14)0.0056 (15)0.0565 (13)0.0105 (12)
C13B0.087 (2)0.048 (2)0.073 (2)0.0112 (14)0.0549 (13)0.0034 (12)
C9B0.0702 (15)0.050 (2)0.0514 (13)0.0125 (13)0.0283 (12)0.0051 (12)
O9B0.0890 (11)0.0620 (13)0.0810 (12)0.0092 (11)0.0542 (10)0.0022 (10)
C12B0.0698 (15)0.0487 (15)0.0573 (14)0.0051 (13)0.0339 (12)0.0001 (12)
C8B0.071 (2)0.057 (2)0.0590 (15)0.003 (2)0.0275 (13)0.0028 (14)
C7B0.092 (2)0.072 (2)0.069 (2)0.008 (2)0.038 (2)0.009 (2)
C6B0.110 (2)0.057 (2)0.084 (2)0.001 (2)0.062 (2)0.010 (2)
C5B0.077 (2)0.076 (2)0.0548 (14)0.019 (2)0.0365 (13)0.0137 (14)
C11B0.073 (2)0.074 (2)0.0488 (14)0.018 (2)0.0247 (13)0.0064 (14)
O8B0.0748 (12)0.0716 (14)0.0676 (12)0.0076 (12)0.0214 (10)0.0110 (11)
C15B0.101 (2)0.051 (2)0.101 (2)0.025 (2)0.041 (2)0.021 (2)
C16B0.106 (2)0.073 (2)0.077 (2)0.016 (2)0.056 (2)0.012 (2)
O16B0.0877 (13)0.096 (2)0.0912 (14)0.0081 (13)0.0374 (12)0.0225 (13)
C17B0.085 (2)0.115 (3)0.095 (3)0.025 (2)0.015 (2)0.003 (3)
C18B0.096 (2)0.108 (3)0.072 (2)0.007 (2)0.038 (2)0.003 (2)
O18B0.101 (2)0.107 (2)0.0738 (14)0.012 (2)0.0286 (13)0.0056 (14)
C19B0.111 (2)0.147 (4)0.062 (2)0.008 (3)0.044 (2)0.009 (2)
C20B0.096 (2)0.124 (3)0.088 (2)0.039 (2)0.045 (2)0.013 (2)
C22B0.097 (2)0.092 (3)0.065 (2)0.002 (2)0.026 (2)0.027 (2)
O1B0.0792 (13)0.0759 (14)0.0521 (10)0.0028 (11)0.0113 (10)0.0128 (10)
OWB0.097 (2)0.119 (2)0.0660 (13)0.026 (2)0.0140 (12)0.0077 (14)
Geometric parameters (Å, º) top
O20A—C20A1.417 (2)O20B—C21B1.420 (3)
O20A—C21A1.402 (3)O20B—C20B1.418 (3)
C21A—C22A1.487 (3)C21B—C22B1.483 (3)
C21A—H21A0.97C21B—H21C0.97
C21A—H21B0.97C21B—H21D0.97
C10A—C14A1.501 (4)C10B—C14B1.490 (4)
C10A—C24A1.529 (4)C10B—C11B1.564 (4)
C10A—C23A1.522 (4)C10B—C23B1.545 (5)
C10A—C11A1.557 (4)C10B—C24B1.556 (4)
C23A—H23A0.96C23B—H23D0.96
C23A—H23B0.96C23B—H23E0.96
C23A—H23C0.96C23B—H23F0.96
C24A—H24A0.96C24B—H24D0.96
C24A—H24B0.96C24B—H24E0.96
C24A—H24C0.96C24B—H24F0.96
C14A—C13A1.381 (2)C14B—C4B1.389 (3)
C14A—C4A1.389 (2)C14B—C13B1.385 (2)
C4A—C3A1.378 (3)C4B—C3B1.376 (3)
C4A—H4A0.93C4B—H4B0.93
C3A—C2A1.381 (2)C3B—C2B1.372 (3)
C3A—H3A0.93C3B—H3B0.93
C2A—C1A1.380 (3)C2B—C1B1.383 (3)
C2A—H2A0.93C2B—H2B0.93
C1A—O1A1.349 (3)C1B—O1B1.361 (3)
C1A—C13A1.408 (3)C1B—C13B1.423 (3)
C13A—C9A1.511 (3)C13B—C9B1.518 (3)
C9A—O9A1.413 (3)C9B—O9B1.466 (4)
C9A—C12A1.447 (4)C9B—C12B1.486 (3)
C9A—H9A0.98C9B—H9B0.98
O9A—H9A10.82O9B—H9B10.82
C12A—C11A1.384 (2)C12B—C8B1.407 (3)
C12A—C8A1.400 (3)C12B—C11B1.384 (2)
C8A—C7A1.357 (4)C8B—C7B1.367 (4)
C8A—O8A1.371 (3)C8B—O8B1.383 (3)
C7A—C6A1.378 (3)C7B—C6B1.378 (3)
C7A—H7A0.93C7B—H7B0.93
C6A—C5A1.382 (3)C6B—C5B1.375 (3)
C6A—H6A0.93C6B—H6B0.93
C5A—C11A1.391 (3)C5B—C11B1.397 (3)
C5A—H5A0.93C5B—H5B0.93
O8A—C15A1.437 (3)O8B—C15B1.427 (3)
C15A—C16A1.484 (3)C15B—C16B1.478 (3)
C15A—H15A0.97C15B—H15C0.97
C15A—H15B0.97C15B—H15D0.97
C16A—O16A1.413 (3)C16B—O16B1.410 (3)
C16A—H16A0.97C16B—H16C0.97
C16A—H16B0.97C16B—H16D0.97
O16A—C17A1.410 (2)O16B—C17B1.425 (3)
C17A—C18A1.495 (4)C17B—C18B1.493 (4)
C17A—H17A0.97C17B—H17C0.97
C17A—H17B0.97C17B—H17D0.97
C18A—O18A1.413 (3)C18B—O18B1.410 (3)
C18A—H18A0.97C18B—H18C0.97
C18A—H18B0.97C18B—H18D0.97
O18A—C19A1.406 (3)O18B—C19B1.416 (3)
C19A—C20A1.479 (5)C19B—C20B1.491 (5)
C19A—H19A0.97C19B—H19C0.97
C19A—H19B0.97C19B—H19D0.97
C20A—H20A0.97C20B—H20C0.97
C20A—H20B0.97C20B—H20D0.97
C22A—O1A1.412 (3)C22B—O1B1.416 (3)
C22A—H22A0.97C22B—H22C0.97
C22A—H22B0.97C22B—H22D0.97
OWA—HWA11.096 (2)OWB—HWB11.178 (3)
C20A—O20A—C21A114.2 (2)C21B—O20B—C20B113.6 (2)
O20A—C21A—C22A109.2 (2)O20B—C21B—C22B112.8 (3)
O20A—C21A—H21A109.85 (14)O20B—C21B—H21C109.0 (2)
C22A—C21A—H21A109.9 (2)C22B—C21B—H21C109.0 (2)
O20A—C21A—H21B109.8 (2)O20B—C21B—H21D109.0 (2)
C22A—C21A—H21B109.8 (2)C22B—C21B—H21D109.0 (2)
H21A—C21A—H21B108.3H21C—C21B—H21D107.8
C14A—C10A—C24A111.3 (2)C14B—C10B—C11B115.4 (2)
C14A—C10A—C23A110.9 (2)C14B—C10B—C23B111.0 (3)
C24A—C10A—C23A109.1 (2)C11B—C10B—C23B104.4 (3)
C14A—C10A—C11A110.8 (2)C14B—C10B—C24B110.1 (3)
C24A—C10A—C11A108.4 (3)C11B—C10B—C24B106.3 (3)
C23A—C10A—C11A106.2 (2)C23B—C10B—C24B109.3 (3)
C10A—C23A—H23A109.5 (2)C10B—C23B—H23D109.5 (2)
C10A—C23A—H23B109.5 (2)C10B—C23B—H23E109.5 (2)
H23A—C23A—H23B109.5H23D—C23B—H23E109.5
C10A—C23A—H23C109.47 (15)C10B—C23B—H23F109.5 (2)
H23A—C23A—H23C109.5H23D—C23B—H23F109.5
H23B—C23A—H23C109.5H23E—C23B—H23F109.5
C10A—C24A—H24A109.5 (2)C10B—C24B—H24D109.5 (2)
C10A—C24A—H24B109.5 (2)C10B—C24B—H24E109.5 (2)
H24A—C24A—H24B109.5H24D—C24B—H24E109.5
C10A—C24A—H24C109.5 (2)C10B—C24B—H24F109.5 (2)
H24A—C24A—H24C109.5H24D—C24B—H24F109.5
H24B—C24A—H24C109.5H24E—C24B—H24F109.5
C13A—C14A—C4A118.9 (2)C4B—C14B—C13B119.8 (2)
C13A—C14A—C10A124.3 (2)C4B—C14B—C10B118.8 (2)
C4A—C14A—C10A116.6 (2)C13B—C14B—C10B121.3 (2)
C3A—C4A—C14A120.3 (2)C3B—C4B—C14B117.1 (3)
C3A—C4A—H4A119.83 (13)C3B—C4B—H4B121.4 (2)
C14A—C4A—H4A119.83 (14)C14B—C4B—H4B121.45 (14)
C4A—C3A—C2A121.3 (2)C4B—C3B—C2B124.8 (3)
C4A—C3A—H3A119.33 (14)C4B—C3B—H3B117.6 (2)
C2A—C3A—H3A119.3 (2)C2B—C3B—H3B117.6 (2)
C3A—C2A—C1A118.9 (2)C3B—C2B—C1B118.7 (3)
C3A—C2A—H2A120.6 (2)C3B—C2B—H2B120.6 (2)
C1A—C2A—H2A120.57 (14)C1B—C2B—H2B120.6 (2)
O1A—C1A—C2A125.9 (2)O1B—C1B—C2B125.3 (2)
O1A—C1A—C13A113.9 (2)O1B—C1B—C13B117.0 (2)
C2A—C1A—C13A120.1 (2)C2B—C1B—C13B117.7 (2)
C14A—C13A—C1A120.3 (2)C14B—C13B—C1B121.7 (2)
C14A—C13A—C9A121.2 (2)C14B—C13B—C9B122.7 (2)
C1A—C13A—C9A118.4 (2)C1B—C13B—C9B115.5 (2)
O9A—C9A—C12A106.5 (2)O9B—C9B—C12B108.5 (2)
O9A—C9A—C13A107.9 (2)O9B—C9B—C13B107.4 (2)
C12A—C9A—C13A114.4 (2)C12B—C9B—C13B113.6 (2)
O9A—C9A—H9A109.29 (11)O9B—C9B—H9B109.10 (12)
C12A—C9A—H9A109.29 (14)C12B—C9B—H9B109.10 (14)
C13A—C9A—H9A109.28 (13)C13B—C9B—H9B109.10 (14)
C9A—O9A—H9A1109.47 (12)C9B—O9B—H9B1109.47 (13)
C11A—C12A—C8A116.9 (2)C8B—C12B—C11B118.9 (2)
C11A—C12A—C9A122.5 (2)C8B—C12B—C9B117.5 (2)
C8A—C12A—C9A120.2 (2)C11B—C12B—C9B123.4 (2)
C7A—C8A—O8A123.9 (2)C7B—C8B—O8B122.6 (2)
C7A—C8A—C12A124.9 (2)C7B—C8B—C12B122.5 (2)
O8A—C8A—C12A111.2 (2)O8B—C8B—C12B114.9 (2)
C8A—C7A—C6A118.4 (3)C8B—C7B—C6B118.2 (3)
C8A—C7A—H7A120.8 (2)C8B—C7B—H7B120.9 (2)
C6A—C7A—H7A120.8 (2)C6B—C7B—H7B120.9 (2)
C5A—C6A—C7A117.9 (3)C5B—C6B—C7B120.4 (3)
C5A—C6A—H6A121.0 (2)C5B—C6B—H6B119.80 (14)
C7A—C6A—H6A121.0 (2)C7B—C6B—H6B119.8 (2)
C6A—C5A—C11A123.8 (3)C6B—C5B—C11B121.9 (2)
C6A—C5A—H5A118.1 (2)C6B—C5B—H5B119.03 (14)
C11A—C5A—H5A118.07 (15)C11B—C5B—H5B119.03 (14)
C12A—C11A—C5A118.1 (2)C12B—C11B—C5B118.0 (2)
C12A—C11A—C10A122.8 (2)C12B—C11B—C10B119.5 (2)
C5A—C11A—C10A119.1 (2)C5B—C11B—C10B122.5 (2)
C8A—O8A—C15A120.1 (2)C8B—O8B—C15B119.7 (2)
O8A—C15A—C16A111.3 (2)O8B—C15B—C16B107.7 (2)
O8A—C15A—H15A109.4 (2)O8B—C15B—H15C110.2 (2)
C16A—C15A—H15A109.4 (2)C16B—C15B—H15C110.2 (2)
O8A—C15A—H15B109.4 (2)O8B—C15B—H15D110.2 (2)
C16A—C15A—H15B109.4 (2)C16B—C15B—H15D110.2 (2)
H15A—C15A—H15B108.0H15C—C15B—H15D108.5
O16A—C16A—C15A110.6 (2)O16B—C16B—C15B111.0 (2)
O16A—C16A—H16A109.5 (2)O16B—C16B—H16C109.4 (2)
C15A—C16A—H16A109.5 (2)C15B—C16B—H16C109.4 (2)
O16A—C16A—H16B109.53 (13)O16B—C16B—H16D109.44 (15)
C15A—C16A—H16B109.5 (2)C15B—C16B—H16D109.4 (2)
H16A—C16A—H16B108.1H16C—C16B—H16D108.0
C17A—O16A—C16A110.7 (2)C16B—O16B—C17B114.0 (2)
O16A—C17A—C18A115.0 (2)O16B—C17B—C18B113.9 (3)
O16A—C17A—H17A108.5 (2)O16B—C17B—H17C108.8 (2)
C18A—C17A—H17A108.5 (2)C18B—C17B—H17C108.8 (2)
O16A—C17A—H17B108.5 (2)O16B—C17B—H17D108.8 (2)
C18A—C17A—H17B108.5 (2)C18B—C17B—H17D108.8 (2)
H17A—C17A—H17B107.5H17C—C17B—H17D107.7
O18A—C18A—C17A109.2 (3)O18B—C18B—C17B109.8 (3)
O18A—C18A—H18A109.8 (2)O18B—C18B—H18C109.7 (2)
C17A—C18A—H18A109.8 (2)C17B—C18B—H18C109.7 (2)
O18A—C18A—H18B109.85 (14)O18B—C18B—H18D109.71 (15)
C17A—C18A—H18B109.84 (14)C17B—C18B—H18D109.7 (2)
H18A—C18A—H18B108.3H18C—C18B—H18D108.2
C19A—O18A—C18A112.4 (2)C18B—O18B—C19B112.9 (3)
O18A—C19A—C20A107.9 (3)O18B—C19B—C20B108.4 (3)
O18A—C19A—H19A110.1 (2)O18B—C19B—H19C110.0 (2)
C20A—C19A—H19A110.1 (2)C20B—C19B—H19C110.0 (2)
O18A—C19A—H19B110.1 (2)O18B—C19B—H19D110.0 (2)
C20A—C19A—H19B110.1 (2)C20B—C19B—H19D110.0 (2)
H19A—C19A—H19B108.4H19C—C19B—H19D108.4
O20A—C20A—C19A116.6 (3)O20B—C20B—C19B114.6 (3)
O20A—C20A—H20A108.2 (2)O20B—C20B—H20C108.6 (2)
C19A—C20A—H20A108.2 (2)C19B—C20B—H20C108.6 (2)
O20A—C20A—H20B108.1 (2)O20B—C20B—H20D108.6 (2)
C19A—C20A—H20B108.2 (2)C19B—C20B—H20D108.6 (2)
H20A—C20A—H20B107.3H20C—C20B—H20D107.6
O1A—C22A—C21A109.3 (2)O1B—C22B—C21B107.3 (3)
O1A—C22A—H22A109.81 (15)O1B—C22B—H22C110.2 (2)
C21A—C22A—H22A109.8 (2)C21B—C22B—H22C110.3 (2)
O1A—C22A—H22B109.8 (2)O1B—C22B—H22D110.3 (2)
C21A—C22A—H22B109.8 (2)C21B—C22B—H22D110.3 (2)
H22A—C22A—H22B108.3H22C—C22B—H22D108.5
C1A—O1A—C22A118.6 (2)C1B—O1B—C22B116.2 (2)
C20A—O20A—C21A—C22A166.5 (3)C20B—O20B—C21B—C22B168.2 (3)
C24A—C10A—C14A—C13A131.7 (3)C11B—C10B—C14B—C4B172.4 (3)
C23A—C10A—C14A—C13A106.7 (3)C23B—C10B—C14B—C4B69.0 (4)
C11A—C10A—C14A—C13A11.0 (4)C24B—C10B—C14B—C4B52.1 (4)
C24A—C10A—C14A—C4A53.2 (4)C11B—C10B—C14B—C13B11.4 (4)
C23A—C10A—C14A—C4A68.4 (3)C23B—C10B—C14B—C13B107.2 (3)
C11A—C10A—C14A—C4A173.9 (3)C24B—C10B—C14B—C13B131.6 (3)
C13A—C14A—C4A—C3A1.6 (5)C13B—C14B—C4B—C3B0.9 (5)
C10A—C14A—C4A—C3A176.9 (3)C10B—C14B—C4B—C3B175.4 (3)
C14A—C4A—C3A—C2A1.1 (5)C14B—C4B—C3B—C2B3.6 (6)
C4A—C3A—C2A—C1A1.3 (5)C4B—C3B—C2B—C1B2.4 (6)
C3A—C2A—C1A—O1A178.7 (3)C3B—C2B—C1B—O1B179.5 (3)
C3A—C2A—C1A—C13A1.0 (5)C3B—C2B—C1B—C13B1.4 (5)
C4A—C14A—C13A—C1A3.9 (4)C4B—C14B—C13B—C1B2.8 (5)
C10A—C14A—C13A—C1A178.9 (3)C10B—C14B—C13B—C1B179.0 (3)
C4A—C14A—C13A—C9A172.5 (3)C4B—C14B—C13B—C9B172.4 (3)
C10A—C14A—C13A—C9A2.5 (4)C10B—C14B—C13B—C9B3.8 (5)
O1A—C1A—C13A—C14A176.1 (3)O1B—C1B—C13B—C14B176.8 (3)
C2A—C1A—C13A—C14A3.6 (4)C2B—C1B—C13B—C14B4.0 (5)
O1A—C1A—C13A—C9A7.4 (4)O1B—C1B—C13B—C9B7.7 (4)
C2A—C1A—C13A—C9A172.9 (3)C2B—C1B—C13B—C9B171.5 (3)
C14A—C13A—C9A—O9A99.8 (3)C14B—C13B—C9B—O9B100.6 (3)
C1A—C13A—C9A—O9A76.7 (3)C1B—C13B—C9B—O9B74.9 (3)
C14A—C13A—C9A—C12A18.6 (4)C14B—C13B—C9B—C12B19.4 (4)
C1A—C13A—C9A—C12A164.9 (3)C1B—C13B—C9B—C12B165.2 (3)
O9A—C9A—C12A—C11A98.2 (3)O9B—C9B—C12B—C8B76.5 (3)
C13A—C9A—C12A—C11A20.9 (4)C13B—C9B—C12B—C8B164.2 (3)
O9A—C9A—C12A—C8A73.7 (3)O9B—C9B—C12B—C11B99.0 (3)
C13A—C9A—C12A—C8A167.2 (3)C13B—C9B—C12B—C11B20.3 (4)
C11A—C12A—C8A—C7A0.0 (5)C11B—C12B—C8B—C7B0.2 (5)
C9A—C12A—C8A—C7A172.3 (3)C9B—C12B—C8B—C7B175.5 (3)
C11A—C12A—C8A—O8A176.6 (3)C11B—C12B—C8B—O8B178.9 (3)
C9A—C12A—C8A—O8A11.0 (4)C9B—C12B—C8B—O8B5.4 (4)
O8A—C8A—C7A—C6A176.9 (3)O8B—C8B—C7B—C6B179.3 (3)
C12A—C8A—C7A—C6A0.6 (6)C12B—C8B—C7B—C6B1.7 (5)
C8A—C7A—C6A—C5A1.0 (6)C8B—C7B—C6B—C5B2.9 (5)
C7A—C6A—C5A—C11A0.8 (6)C7B—C6B—C5B—C11B2.3 (5)
C8A—C12A—C11A—C5A0.3 (4)C8B—C12B—C11B—C5B0.9 (4)
C9A—C12A—C11A—C5A171.9 (3)C9B—C12B—C11B—C5B174.5 (3)
C8A—C12A—C11A—C10A179.6 (3)C8B—C12B—C11B—C10B178.5 (3)
C9A—C12A—C11A—C10A7.4 (5)C9B—C12B—C11B—C10B6.0 (4)
C6A—C5A—C11A—C12A0.1 (5)C6B—C5B—C11B—C12B0.3 (4)
C6A—C5A—C11A—C10A179.2 (3)C6B—C5B—C11B—C10B179.7 (3)
C14A—C10A—C11A—C12A8.8 (4)C14B—C10B—C11B—C12B10.4 (4)
C24A—C10A—C11A—C12A131.2 (3)C23B—C10B—C11B—C12B111.7 (3)
C23A—C10A—C11A—C12A111.7 (3)C24B—C10B—C11B—C12B132.8 (3)
C14A—C10A—C11A—C5A171.9 (3)C14B—C10B—C11B—C5B169.0 (3)
C24A—C10A—C11A—C5A49.5 (4)C23B—C10B—C11B—C5B68.9 (3)
C23A—C10A—C11A—C5A67.6 (4)C24B—C10B—C11B—C5B46.6 (4)
C7A—C8A—O8A—C15A1.5 (5)C7B—C8B—O8B—C15B13.5 (5)
C12A—C8A—O8A—C15A178.3 (3)C12B—C8B—O8B—C15B165.5 (3)
C8A—O8A—C15A—C16A172.3 (2)C8B—O8B—C15B—C16B162.3 (3)
O8A—C15A—C16A—O16A71.6 (3)O8B—C15B—C16B—O16B71.0 (3)
C15A—C16A—O16A—C17A168.1 (3)C15B—C16B—O16B—C17B162.0 (3)
C16A—O16A—C17A—C18A74.3 (4)C16B—O16B—C17B—C18B77.2 (4)
O16A—C17A—C18A—O18A64.0 (4)O16B—C17B—C18B—O18B62.7 (4)
C17A—C18A—O18A—C19A179.6 (3)C17B—C18B—O18B—C19B178.1 (3)
C18A—O18A—C19A—C20A177.5 (3)C18B—O18B—C19B—C20B179.9 (3)
C21A—O20A—C20A—C19A73.0 (4)C21B—O20B—C20B—C19B76.2 (4)
O18A—C19A—C20A—O20A64.7 (5)O18B—C19B—C20B—O20B65.9 (4)
O20A—C21A—C22A—O1A71.2 (3)O20B—C21B—C22B—O1B69.9 (4)
C2A—C1A—O1A—C22A14.7 (5)C2B—C1B—O1B—C22B0.9 (5)
C13A—C1A—O1A—C22A165.1 (3)C13B—C1B—O1B—C22B178.2 (3)
C21A—C22A—O1A—C1A163.4 (3)C21B—C22B—O1B—C1B171.7 (3)
(neutron) top
Crystal data top
C24H30O6·H2OF(000) = 928
Mr = 432.49Dx = 1.303 Mg m3
Monoclinic, P21? radiation, λ = 1.538 and 1.312 Å
a = 12.605 (5) ÅCell parameters from 25 reflections
b = 14.458 (3) Åθ = 25–30°
c = 13.588 (2) ŵ = 0.00 mm1
β = 117.12 (2)°T = 15 K
V = 2204.1 (10) Å3Plate, colourless
Z = 42.5 × 1.6 × 0.2 mm
Data collection top
D19 ILL ω
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 46.1°, θmin = 3.7°
Graphite monochromatorh = 1011
1931 measured reflectionsk = 013
1931 independent reflectionsl = 912
1881 reflections with I > 2σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046Calculated w = 1/[σ2(Fo2) + (0.1016P)2 + 0.5955P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.132(Δ/σ)max = 0.123
S = 0.78Δρmax = 0.06 e Å3
1881 reflectionsΔρmin = 0.06 e Å3
507 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
1 restraintAbsolute structure parameter: 10.0 (100)
Primary atom site location: structure-invariant direct methods
Crystal data top
C24H30O6·H2OV = 2204.1 (10) Å3
Mr = 432.49Z = 4
Monoclinic, P21? radiation, λ = 1.538 and 1.312 Å
a = 12.605 (5) ŵ = 0.00 mm1
b = 14.458 (3) ÅT = 15 K
c = 13.588 (2) Å2.5 × 1.6 × 0.2 mm
β = 117.12 (2)°
Data collection top
D19 ILL ω
diffractometer
1881 reflections with I > 2σ(I)
1931 measured reflectionsRint = 0.000
1931 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046(Δ/σ)max = 0.123
wR(F2) = 0.132Δρmax = 0.06 e Å3
S = 0.78Δρmin = 0.06 e Å3
1881 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
507 parametersAbsolute structure parameter: 10.0 (100)
1 restraint
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 on F2 for ALL reflections except for 50 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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*/UeqOcc. (<1)
O1A1.0310 (9)1.2748 (9)0.1040 (9)0.042 (3)*1.06 (5)
C1A0.9244 (8)1.2716 (8)0.0017 (8)0.014 (2)*1.06 (5)
C2A0.8861 (7)1.3479 (7)0.0635 (7)0.006 (2)*1.06 (5)
C3A0.7772 (8)1.3367 (7)0.1633 (7)0.010 (2)*1.06 (5)
C4A0.7108 (8)1.2618 (7)0.1854 (7)0.008 (2)*1.06 (5)
C5A0.6499 (8)0.9442 (7)0.0627 (8)0.009 (3)*1.06 (5)
C6A0.6938 (8)0.8734 (7)0.0227 (7)0.006 (2)*1.06 (5)
C7A0.8037 (8)0.8843 (7)0.1134 (7)0.004 (2)*1.06 (5)
O8A0.9789 (9)0.9838 (8)0.2145 (9)0.008 (3)*0.83 (4)
C8A0.8701 (8)0.9630 (7)0.1275 (8)0.007 (2)*1.06 (5)
O9A1.0110 (12)1.0712 (8)0.0351 (9)0.009 (3)*0.83 (4)
C9A0.9144 (8)1.1082 (8)0.0570 (8)0.016 (3)*1.06 (5)
C10A0.6738 (8)1.0973 (8)0.1401 (7)0.014 (2)*1.06 (5)
C11A0.7175 (8)1.0263 (8)0.0480 (8)0.016 (3)*1.06 (5)
C12A0.8295 (7)1.0345 (6)0.0453 (7)0.004 (2)*1.06 (5)
C13A0.8575 (7)1.1926 (7)0.0218 (7)0.006 (2)*1.06 (5)
C14A0.7501 (7)1.1833 (7)0.1107 (7)0.007 (2)*1.06 (5)
C15A1.0213 (8)0.9183 (7)0.3038 (7)0.009 (2)*1.06 (5)
O16A1.2297 (9)0.9671 (8)0.3749 (9)0.017 (3)*0.83 (4)
C16A1.1303 (9)0.9540 (8)0.3998 (8)0.015 (3)*1.06 (5)
C17A1.3347 (8)0.9811 (7)0.4697 (8)0.006 (2)*1.06 (5)
O18A1.3513 (10)1.1365 (9)0.4303 (10)0.020 (3)*0.83 (4)
C18A1.3469 (9)1.0811 (7)0.5136 (8)0.008 (2)*1.06 (5)
C19A1.3678 (10)1.2326 (8)0.4612 (9)0.017 (3)*1.06 (5)
O20A1.2752 (8)1.2881 (7)0.2708 (8)0.005 (2)*0.83 (4)
C20A1.3758 (8)1.2875 (7)0.3687 (7)0.014 (2)*1.06 (5)
C21A1.1768 (7)1.3369 (7)0.2663 (7)0.008 (2)*1.06 (5)
C22A1.0850 (7)1.3605 (7)0.1461 (6)0.003 (2)*1.06 (5)
C23A0.6799 (10)1.0533 (7)0.2422 (8)0.015 (3)*1.06 (5)
C24A0.5420 (8)1.1211 (7)0.1683 (9)0.014 (3)*1.06 (5)
H3A0.7506 (16)1.3933 (14)0.2223 (15)0.024 (5)*0.94 (4)
H2A0.9420 (13)1.4129 (13)0.0490 (12)0.009 (4)*0.94 (4)
H4A0.6225 (12)1.2588 (11)0.2578 (11)0.004 (4)*0.94 (4)
H5A0.5656 (16)0.9403 (13)0.1314 (15)0.026 (5)*0.94 (4)
H6A0.641 (2)0.8176 (19)0.010 (2)0.055 (7)*0.94 (4)
H7A0.8399 (14)0.8296 (13)0.1840 (13)0.017 (4)*0.94 (4)
H9A0.9651 (17)1.1251 (13)0.1416 (16)0.028 (5)*0.94 (4)
H9A11.071 (3)1.0774 (16)0.081 (2)0.037 (6)*0.94 (4)
H15A1.0568 (13)0.8547 (12)0.2701 (12)0.011 (4)*0.94 (4)
H15B0.9557 (18)0.9002 (17)0.3340 (16)0.039 (6)*0.94 (4)
H16A1.1111 (16)1.0277 (14)0.4158 (15)0.032 (5)*0.94 (4)
H16B1.1595 (14)0.9103 (14)0.4738 (14)0.016 (4)*0.94 (4)
H17A1.4115 (19)0.9659 (19)0.4500 (18)0.045 (6)*0.94 (4)
H17B1.3440 (12)0.9350 (11)0.5390 (12)0.000 (4)*0.94 (4)
H18A1.2851 (18)1.1028 (15)0.5339 (16)0.035 (6)*0.94 (4)
H18B1.428 (2)1.0912 (18)0.5913 (19)0.044 (6)*0.94 (4)
H19A1.4414 (18)1.2429 (16)0.5343 (17)0.036 (5)*0.94 (4)
H19B1.2888 (16)1.2507 (14)0.4739 (14)0.025 (5)*0.94 (4)
H20A1.3919 (13)1.3613 (12)0.4041 (12)0.011 (4)*0.94 (4)
H20B1.4432 (14)1.2519 (13)0.3490 (13)0.026 (5)*0.94 (4)
H21A1.2101 (17)1.4075 (17)0.3021 (16)0.035 (5)*0.94 (4)
H21B1.1324 (19)1.3023 (17)0.3046 (17)0.036 (5)*0.94 (4)
H22A1.0322 (14)1.4147 (14)0.1394 (13)0.023 (5)*0.94 (4)
H22B1.1379 (15)1.3773 (13)0.0982 (13)0.019 (5)*0.94 (4)
H23A0.6141 (15)0.9877 (13)0.2659 (14)0.024 (5)*0.94 (4)
H23B0.761 (2)1.0395 (18)0.230 (2)0.053 (7)*0.94 (4)
H23C0.6311 (15)1.0976 (14)0.3194 (15)0.030 (5)*0.94 (4)
H24A0.5348 (18)1.1520 (17)0.0984 (19)0.045 (6)*0.94 (4)
H24B0.4868 (16)1.0636 (15)0.1914 (14)0.023 (5)*0.94 (4)
H24C0.5045 (13)1.1675 (14)0.2422 (14)0.023 (5)*0.94 (4)
OWA1.2233 (9)1.0882 (9)0.1936 (9)0.017 (3)*0.83 (4)
HWA11.2353 (16)1.1577 (14)0.2101 (16)0.026 (5)*0.94 (4)
HWA21.24111.06360.25990.023 (5)*0.94 (4)
O1B0.9734 (9)1.0879 (8)0.7188 (9)0.012 (3)*0.83 (4)
C1B0.8698 (8)1.1051 (7)0.6283 (8)0.010 (2)*1.06 (5)
C2B0.8031 (9)1.1869 (8)0.6180 (8)0.017 (3)*1.06 (5)
C3B0.6934 (9)1.1942 (8)0.5191 (9)0.018 (3)*1.06 (5)
C4B0.6506 (9)1.1274 (8)0.4418 (9)0.016 (3)*1.06 (5)
C5B0.7085 (9)0.8125 (8)0.3163 (8)0.012 (2)*1.06 (5)
C6B0.7784 (7)0.7261 (7)0.3416 (7)0.003 (2)*1.06 (5)
C7B0.8873 (9)0.7214 (9)0.4337 (8)0.016 (3)*1.06 (5)
O8B1.0294 (8)0.8019 (8)0.6002 (7)0.006 (3)*0.83 (4)
C8B0.9271 (7)0.7975 (7)0.5094 (7)0.002 (2)*1.06 (5)
O9B1.0000 (9)1.0033 (8)0.5245 (7)0.009 (3)*0.83 (4)
C9B0.9169 (7)0.9626 (7)0.5562 (7)0.003 (2)*1.06 (5)
C10B0.6715 (7)0.9755 (7)0.3573 (6)0.002 (2)*1.06 (5)
C11B0.7488 (8)0.8868 (7)0.3854 (7)0.009 (2)*1.06 (5)
C12B0.8613 (8)0.8831 (7)0.4857 (7)0.010 (2)*1.06 (5)
C13B0.8294 (8)1.0388 (7)0.5426 (8)0.013 (3)*1.06 (5)
C14B0.7211 (7)1.0496 (6)0.4515 (7)0.001 (2)*1.06 (5)
C15B1.0925 (8)0.7181 (8)0.6450 (8)0.017 (2)*1.06 (5)
O16B1.2731 (10)0.7867 (8)0.7657 (9)0.019 (3)*0.83 (4)
C16B1.1778 (8)0.7292 (7)0.7636 (7)0.012 (2)*1.06 (5)
C17B1.3786 (8)0.7797 (7)0.8757 (7)0.009 (2)*1.06 (5)
O18B1.3555 (9)0.9309 (8)0.9324 (8)0.010 (3)*0.83 (4)
C18B1.3669 (9)0.8383 (7)0.9646 (8)0.008 (2)*1.06 (5)
C19B1.3509 (9)0.9916 (8)1.0128 (9)0.019 (3)*1.06 (5)
O20B1.2316 (8)1.1126 (7)0.8767 (8)0.006 (3)*0.83 (4)
C20B1.3403 (9)1.0906 (8)0.9756 (9)0.016 (3)*1.06 (5)
C21B1.1318 (8)1.1146 (7)0.8986 (8)0.010 (2)*1.06 (5)
C22B1.0256 (8)1.1579 (7)0.7996 (8)0.010 (2)*1.06 (5)
C23B0.6718 (8)1.0206 (7)0.2541 (7)0.006 (2)*1.06 (5)
C24B0.5472 (8)0.9471 (7)0.3330 (8)0.007 (2)*1.06 (5)
H4B0.5696 (18)1.1413 (15)0.3726 (17)0.039 (6)*0.94 (4)
H3B0.6450 (14)1.2614 (11)0.5116 (13)0.010 (4)*0.94 (4)
H2B0.8243 (15)1.2366 (16)0.6713 (16)0.031 (5)*0.94 (4)
H6B0.7459 (16)0.6684 (16)0.2889 (17)0.030 (5)*0.94 (4)
H5B0.636 (2)0.8165 (18)0.2401 (19)0.049 (6)*0.94 (4)
H7B0.9317 (19)0.6637 (19)0.4523 (18)0.038 (6)*0.94 (4)
H9B0.9553 (13)0.9325 (11)0.6423 (12)0.009 (4)*0.94 (4)
H15C1.1305 (16)0.6806 (14)0.5991 (15)0.030 (5)*0.94 (4)
H15D1.0165 (13)0.6661 (12)0.6469 (13)0.018 (4)*0.94 (4)
H16C1.1334 (15)0.7673 (14)0.8086 (15)0.021 (4)*0.94 (4)
H16D1.2112 (14)0.6672 (14)0.8121 (14)0.019 (4)*0.94 (4)
H17C1.4541 (13)0.8028 (11)0.8647 (11)0.014 (4)*0.94 (4)
H17D1.4063 (19)0.7119 (18)0.8970 (17)0.047 (6)*0.94 (4)
H18C1.2963 (15)0.8103 (13)0.9810 (13)0.019 (5)*0.94 (4)
H18D1.4551 (15)0.8286 (14)1.0456 (14)0.026 (5)*0.94 (4)
H19C1.4296 (15)0.9860 (13)1.0900 (15)0.017 (5)*0.94 (4)
H19D1.2667 (13)0.9754 (11)1.0266 (12)0.012 (4)*0.94 (4)
H20C1.348 (2)1.137 (2)1.044 (2)0.066 (8)*0.94 (4)
H20D1.4092 (14)1.1034 (13)0.9510 (13)0.016 (4)*0.94 (4)
H21C1.1056 (14)1.0536 (12)0.9267 (12)0.016 (4)*0.94 (4)
H21D1.1499 (19)1.1637 (19)0.9662 (19)0.045 (6)*0.94 (4)
H22C0.9596 (14)1.1767 (13)0.8278 (12)0.015 (4)*0.94 (4)
H22D1.0378 (17)1.2195 (17)0.7669 (16)0.037 (5)*0.94 (4)
H23D0.7698 (15)1.0413 (12)0.2734 (14)0.015 (4)*0.94 (4)
H23E0.6298 (17)1.0817 (17)0.2301 (16)0.035 (5)*0.94 (4)
H23F0.6521 (14)0.9706 (14)0.1916 (14)0.022 (4)*0.94 (4)
H24D0.5086 (14)0.8944 (15)0.2705 (16)0.028 (5)*0.94 (4)
H24E0.4833 (19)1.0078 (17)0.3096 (17)0.039 (5)*0.94 (4)
H24F0.5480 (14)0.9120 (14)0.4046 (14)0.022 (5)*0.94 (4)
H9B11.0850 (14)0.9887 (11)0.5922 (12)0.009 (4)*0.94 (4)
OWB1.2310 (9)0.9760 (9)0.6960 (9)0.013 (3)*0.83 (4)
HWB11.2264 (16)1.0171 (14)0.7547 (15)0.047 (6)*0.94 (4)
HWB21.2508 (17)0.9192 (17)0.7269 (17)0.034 (5)*0.94 (4)
Geometric parameters (Å, º) top
C10A—C14A1.51 (2)C10B—C24B1.503 (13)
C10A—C11A1.514 (15)C10B—C23B1.549 (13)
C10A—C24A1.563 (14)C10B—C14B1.564 (13)
C10A—C23A1.560 (15)C10B—C11B1.549 (15)
C23A—H23A1.20 (2)C23B—H23D1.18 (2)
C23A—H23B0.97 (3)C23B—H23E1.00 (3)
C23A—H23C1.14 (2)C23B—H23F1.06 (2)
C24A—H24A1.09 (3)C24B—H24D1.08 (3)
C24A—H24B1.04 (3)C24B—H24E1.13 (3)
C24A—H24C1.12 (2)C24B—H24F1.09 (2)
C14A—C13A1.349 (12)C14B—C13B1.371 (13)
C14A—C4A1.450 (14)C14B—C4B1.402 (15)
C4A—C3A1.317 (14)C4B—C3B1.35 (2)
C4A—H4A1.10 (2)C4B—H4B1.04 (3)
C3A—C2A1.432 (13)C3B—C2B1.426 (15)
C3A—H3A1.09 (2)C3B—H3B1.13 (2)
C2A—C1A1.358 (14)C2B—C1B1.42 (2)
C2A—H2A1.14 (2)C2B—H2B0.97 (3)
C1A—C13A1.368 (14)C1B—O1B1.347 (14)
C1A—O1A1.427 (14)C1B—C13B1.412 (15)
C13A—C9A1.565 (14)C13B—C9B1.511 (14)
C9A—C12A1.466 (14)C9B—O9B1.428 (14)
C9A—O9A1.48 (2)C9B—C12B1.455 (14)
C9A—H9A1.06 (2)C9B—H9B1.13 (2)
O9A—H9A10.73 (4)O9B—H9B11.07 (2)
C12A—C11A1.408 (14)C12B—C8B1.442 (14)
C12A—C8A1.435 (13)C12B—C11B1.453 (12)
C8A—C7A1.373 (14)C8B—O8B1.319 (12)
C8A—O8A1.375 (14)C8B—C7B1.432 (14)
C7A—C6A1.380 (13)C7B—C6B1.374 (13)
C7A—H7A1.16 (2)C7B—H7B0.97 (3)
C6A—C5A1.455 (14)C6B—C5B1.475 (15)
C6A—H6A1.01 (3)C6B—H6B1.05 (3)
C5A—C11A1.42 (2)C5B—C11B1.363 (15)
C5A—H5A1.05 (2)C5B—H5B1.02 (3)
O8A—C15A1.44 (2)O8B—C15B1.43 (2)
C15A—C16A1.490 (14)C15B—C16B1.483 (14)
C15A—H15A1.20 (2)C15B—H15C1.09 (2)
C15A—H15B1.11 (3)C15B—H15D1.23 (2)
C16A—O16A1.451 (15)C16B—O16B1.451 (15)
C16A—H16A1.14 (2)C16B—H16C1.14 (2)
C16A—H16B1.10 (2)C16B—H16D1.08 (2)
O16A—C17A1.378 (14)O16B—C17B1.483 (14)
C17A—C18A1.54 (2)C17B—C18B1.536 (15)
C17A—H17A1.14 (3)C17B—H17C1.08 (2)
C17A—H17B1.12 (2)C17B—H17D1.04 (3)
C18A—O18A1.41 (2)C18B—O18B1.40 (2)
C18A—H18A0.99 (3)C18B—H18C1.09 (2)
C18A—H18B1.09 (3)C18B—H18D1.16 (2)
O18A—C19A1.44 (2)O18B—C19B1.42 (2)
C19A—C20A1.53 (2)C19B—C20B1.50 (2)
C19A—H19A1.02 (3)C19B—H19C1.07 (2)
C19A—H19B1.12 (2)C19B—H19D1.18 (2)
C20A—O20A1.356 (13)C20B—O20B1.450 (14)
C20A—H20A1.15 (2)C20B—H20C1.12 (4)
C20A—H20B1.13 (2)C20B—H20D1.08 (2)
O20A—C21A1.404 (14)O20B—C21B1.419 (13)
C21A—C22A1.549 (12)C21B—C22B1.534 (14)
C21A—H21A1.13 (3)C21B—H21C1.07 (2)
C21A—H21B1.05 (3)C21B—H21D1.10 (3)
C22A—O1A1.40 (2)C22B—O1B1.42 (2)
C22A—H22A1.00 (2)C22B—H22C1.10 (2)
C22A—H22B1.15 (2)C22B—H22D1.04 (3)
OWA—HWA11.03 (3)OWB—HWB11.02 (3)
OWA—HWA20.897 (11)OWB—HWB20.91 (3)
C14A—C10A—C11A113.1 (7)C24B—C10B—C23B110.4 (7)
C14A—C10A—C24A111.1 (9)C24B—C10B—C14B110.8 (7)
C11A—C10A—C24A107.3 (7)C23B—C10B—C14B106.7 (8)
C14A—C10A—C23A106.7 (7)C24B—C10B—C11B107.6 (8)
C11A—C10A—C23A108.2 (9)C23B—C10B—C11B108.1 (7)
C24A—C10A—C23A110.4 (8)C14B—C10B—C11B113.2 (6)
C10A—C23A—H23A104.6 (11)C10B—C23B—H23D109.9 (11)
C10A—C23A—H23B113.8 (17)C10B—C23B—H23E116.5 (12)
H23A—C23A—H23B115 (2)H23D—C23B—H23E101.2 (17)
C10A—C23A—H23C111.4 (14)C10B—C23B—H23F110.0 (13)
H23A—C23A—H23C100.3 (15)H23D—C23B—H23F101.1 (14)
H23B—C23A—H23C110.8 (19)H23E—C23B—H23F116.5 (17)
C10A—C24A—H24A112.2 (14)C10B—C24B—H24D114.7 (11)
C10A—C24A—H24B113.0 (14)C10B—C24B—H24E112.7 (14)
H24A—C24A—H24B106.3 (18)H24D—C24B—H24E108.6 (17)
C10A—C24A—H24C108.6 (10)C10B—C24B—H24F110.2 (12)
H24A—C24A—H24C111.5 (18)H24D—C24B—H24F101.0 (17)
H24B—C24A—H24C105.0 (16)H24E—C24B—H24F109.0 (17)
C13A—C14A—C4A115.6 (8)C13B—C14B—C4B120.2 (9)
C13A—C14A—C10A125.2 (9)C13B—C14B—C10B121.5 (8)
C4A—C14A—C10A119.1 (7)C4B—C14B—C10B118.3 (7)
C3A—C4A—C14A120.3 (8)C3B—C4B—C14B119.4 (9)
C3A—C4A—H4A120.9 (12)C3B—C4B—H4B116.4 (16)
C14A—C4A—H4A118.7 (12)C14B—C4B—H4B123.7 (15)
C4A—C3A—C2A122.9 (9)C4B—C3B—C2B123.7 (10)
C4A—C3A—H3A120.1 (13)C4B—C3B—H3B122.7 (13)
C2A—C3A—H3A117.0 (13)C2B—C3B—H3B113.6 (12)
C1A—C2A—C3A115.4 (9)C3B—C2B—C1B115.5 (10)
C1A—C2A—H2A123.4 (11)C3B—C2B—H2B118.0 (15)
C3A—C2A—H2A120.5 (11)C1B—C2B—H2B126.5 (14)
C2A—C1A—C13A121.8 (7)O1B—C1B—C13B117.6 (10)
C2A—C1A—O1A120.4 (9)O1B—C1B—C2B121.8 (10)
C13A—C1A—O1A117.5 (9)C13B—C1B—C2B120.6 (8)
C14A—C13A—C1A123.5 (8)C14B—C13B—C1B120.3 (9)
C14A—C13A—C9A119.6 (8)C14B—C13B—C9B124.4 (9)
C1A—C13A—C9A116.8 (7)C1B—C13B—C9B115.2 (8)
C12A—C9A—O9A110.1 (9)O9B—C9B—C12B109.1 (8)
C12A—C9A—C13A114.1 (8)O9B—C9B—C13B104.9 (8)
O9A—C9A—C13A107.9 (8)C12B—C9B—C13B112.9 (7)
C12A—C9A—H9A109.6 (13)O9B—C9B—H9B116.4 (11)
O9A—C9A—H9A99.0 (12)C12B—C9B—H9B103.2 (11)
C13A—C9A—H9A115.1 (14)C13B—C9B—H9B110.6 (11)
C9A—O9A—H9A1114.0 (17)C9B—O9B—H9B1104.1 (11)
C11A—C12A—C8A119.7 (8)C8B—C12B—C11B117.2 (8)
C11A—C12A—C9A122.8 (8)C8B—C12B—C9B118.4 (7)
C8A—C12A—C9A117.1 (8)C11B—C12B—C9B124.1 (8)
C7A—C8A—O8A127.4 (9)O8B—C8B—C12B112.6 (8)
C7A—C8A—C12A120.7 (8)O8B—C8B—C7B125.6 (9)
O8A—C8A—C12A111.9 (9)C12B—C8B—C7B121.5 (7)
C8A—C7A—C6A121.2 (9)C6B—C7B—C8B119.5 (10)
C8A—C7A—H7A117.5 (11)C6B—C7B—H7B119.8 (16)
C6A—C7A—H7A121.0 (11)C8B—C7B—H7B120.2 (15)
C7A—C6A—C5A119.6 (9)C7B—C6B—C5B119.8 (9)
C7A—C6A—H6A123.8 (16)C7B—C6B—H6B119.8 (14)
C5A—C6A—H6A116.6 (16)C5B—C6B—H6B120.4 (13)
C11A—C5A—C6A119.3 (9)C11B—C5B—C6B120.7 (8)
C11A—C5A—H5A118.0 (14)C11B—C5B—H5B122.1 (17)
C6A—C5A—H5A122.4 (13)C6B—C5B—H5B116.6 (16)
C12A—C11A—C5A119.2 (9)C5B—C11B—C12B121.0 (9)
C12A—C11A—C10A121.6 (9)C5B—C11B—C10B119.2 (7)
C5A—C11A—C10A118.7 (8)C12B—C11B—C10B119.8 (8)
C8A—O8A—C15A115.1 (9)C8B—O8B—C15B118.4 (9)
O8A—C15A—C16A110.5 (9)O8B—C15B—C16B111.0 (9)
O8A—C15A—H15A104.0 (11)O8B—C15B—H15C119.0 (13)
C16A—C15A—H15A104.1 (10)C16B—C15B—H15C112.8 (12)
O8A—C15A—H15B114.6 (14)O8B—C15B—H15D103.9 (11)
C16A—C15A—H15B107.7 (12)C16B—C15B—H15D103.3 (10)
H15A—C15A—H15B115.4 (17)H15C—C15B—H15D105.0 (16)
O16A—C16A—C15A113.0 (8)C15B—C16B—O16B105.5 (8)
O16A—C16A—H16A101.8 (13)C15B—C16B—H16C110.2 (11)
C15A—C16A—H16A107.5 (11)O16B—C16B—H16C108.5 (13)
O16A—C16A—H16B108.8 (12)C15B—C16B—H16D117.5 (13)
C15A—C16A—H16B113.1 (13)O16B—C16B—H16D112.0 (12)
H16A—C16A—H16B112.1 (15)H16C—C16B—H16D103.0 (15)
C17A—O16A—C16A111.4 (9)C17B—O16B—C16B109.5 (9)
O16A—C17A—C18A112.5 (9)O16B—C17B—C18B113.1 (8)
O16A—C17A—H17A108.1 (13)O16B—C17B—H17C106.3 (11)
C18A—C17A—H17A109.0 (16)C18B—C17B—H17C110.2 (12)
O16A—C17A—H17B112.8 (12)O16B—C17B—H17D112.2 (15)
C18A—C17A—H17B106.2 (11)C18B—C17B—H17D116.3 (13)
H17A—C17A—H17B108.0 (16)H17C—C17B—H17D97.1 (16)
O18A—C18A—C17A104.8 (9)O18B—C18B—C17B108.4 (8)
O18A—C18A—H18A111.6 (14)O18B—C18B—H18C116.4 (13)
C17A—C18A—H18A116.9 (15)C17B—C18B—H18C109.6 (13)
O18A—C18A—H18B109.8 (16)O18B—C18B—H18D109.3 (13)
C17A—C18A—H18B112.6 (16)C17B—C18B—H18D106.6 (12)
H18A—C18A—H18B101.2 (19)H18C—C18B—H18D106.2 (14)
C19A—O18A—C18A111.6 (10)C19B—O18B—C18B112.7 (9)
O18A—C19A—C20A108.5 (9)O18B—C19B—C20B110.9 (10)
O18A—C19A—H19A111.9 (16)O18B—C19B—H19C111.2 (14)
C20A—C19A—H19A110.8 (15)C20B—C19B—H19C107.7 (14)
O18A—C19A—H19B104.6 (14)O18B—C19B—H19D110.6 (12)
C20A—C19A—H19B113.8 (13)C20B—C19B—H19D107.1 (12)
H19A—C19A—H19B107.2 (16)H19C—C19B—H19D109.1 (15)
O20A—C20A—C19A115.2 (8)O20B—C20B—C19B115.0 (10)
O20A—C20A—H20A108.3 (11)O20B—C20B—H20C109.1 (17)
C19A—C20A—H20A101.7 (10)C19B—C20B—H20C109.5 (18)
O20A—C20A—H20B103.8 (11)O20B—C20B—H20D103.3 (12)
C19A—C20A—H20B107.3 (12)C19B—C20B—H20D107.9 (14)
H20A—C20A—H20B121.1 (14)H20C—C20B—H20D112 (2)
C20A—O20A—C21A117.3 (9)C21B—O20B—C20B111.4 (8)
O20A—C21A—C22A112.2 (7)O20B—C21B—C22B109.1 (8)
O20A—C21A—H21A106.8 (12)O20B—C21B—H21C120.3 (13)
C22A—C21A—H21A102.0 (13)C22B—C21B—H21C111.2 (11)
O20A—C21A—H21B113.6 (15)O20B—C21B—H21D108.8 (14)
C22A—C21A—H21B108.5 (13)C22B—C21B—H21D103.7 (15)
H21A—C21A—H21B113.3 (17)H21C—C21B—H21D102.3 (17)
O1A—C22A—C21A103.0 (8)O1B—C22B—C21B107.4 (9)
O1A—C22A—H22A118.3 (12)O1B—C22B—H22C106.8 (12)
C21A—C22A—H22A114.5 (11)C21B—C22B—H22C107.0 (11)
O1A—C22A—H22B104.7 (12)O1B—C22B—H22D112.9 (15)
C21A—C22A—H22B107.2 (10)C21B—C22B—H22D119.0 (13)
H22A—C22A—H22B108.3 (15)H22C—C22B—H22D102.9 (17)
C22A—O1A—C1A119.5 (10)C1B—O1B—C22B119.3 (10)
HWA1—OWA—HWA2102.9 (14)HWB1—OWB—HWB2105.6 (18)
C11A—C10A—C14A—C13A11.4 (13)C24B—C10B—C14B—C13B128.0 (9)
C24A—C10A—C14A—C13A132.1 (9)C23B—C10B—C14B—C13B111.8 (9)
C23A—C10A—C14A—C13A107.5 (10)C11B—C10B—C14B—C13B7.0 (11)
C11A—C10A—C14A—C4A172.4 (7)C24B—C10B—C14B—C4B50.7 (10)
C24A—C10A—C14A—C4A51.7 (10)C23B—C10B—C14B—C4B69.5 (9)
C23A—C10A—C14A—C4A68.7 (10)C11B—C10B—C14B—C4B171.7 (8)
C13A—C14A—C4A—C3A1.5 (13)C13B—C14B—C4B—C3B4.2 (14)
C10A—C14A—C4A—C3A178.1 (8)C10B—C14B—C4B—C3B177.1 (8)
C14A—C4A—C3A—C2A3.9 (14)C14B—C4B—C3B—C2B6.5 (16)
C4A—C3A—C2A—C1A7.5 (13)C4B—C3B—C2B—C1B3.1 (15)
C3A—C2A—C1A—C13A5.8 (13)C3B—C2B—C1B—O1B178.0 (9)
C3A—C2A—C1A—O1A179.2 (8)C3B—C2B—C1B—C13B2.4 (14)
C4A—C14A—C13A—C1A3.2 (12)C4B—C14B—C13B—C1B1.1 (13)
C10A—C14A—C13A—C1A179.5 (9)C10B—C14B—C13B—C1B177.6 (8)
C4A—C14A—C13A—C9A173.3 (8)C4B—C14B—C13B—C9B174.0 (9)
C10A—C14A—C13A—C9A3.0 (13)C10B—C14B—C13B—C9B7.3 (13)
C2A—C1A—C13A—C14A0.6 (15)O1B—C1B—C13B—C14B176.0 (9)
O1A—C1A—C13A—C14A174.2 (9)C2B—C1B—C13B—C14B4.4 (14)
C2A—C1A—C13A—C9A177.3 (7)O1B—C1B—C13B—C9B8.5 (12)
O1A—C1A—C13A—C9A9.2 (13)C2B—C1B—C13B—C9B171.2 (8)
C14A—C13A—C9A—C12A17.6 (13)C14B—C13B—C9B—O9B97.2 (10)
C1A—C13A—C9A—C12A165.6 (7)C1B—C13B—C9B—O9B78.2 (10)
C14A—C13A—C9A—O9A105.1 (10)C14B—C13B—C9B—C12B21.5 (13)
C1A—C13A—C9A—O9A71.7 (12)C1B—C13B—C9B—C12B163.1 (8)
O9A—C9A—C12A—C11A103.4 (10)O9B—C9B—C12B—C8B78.9 (11)
C13A—C9A—C12A—C11A18.1 (13)C13B—C9B—C12B—C8B164.9 (7)
O9A—C9A—C12A—C8A69.3 (11)O9B—C9B—C12B—C11B94.0 (10)
C13A—C9A—C12A—C8A169.2 (8)C13B—C9B—C12B—C11B22.3 (12)
C11A—C12A—C8A—C7A3.4 (13)C11B—C12B—C8B—O8B178.1 (8)
C9A—C12A—C8A—C7A169.5 (9)C9B—C12B—C8B—O8B4.8 (12)
C11A—C12A—C8A—O8A177.8 (8)C11B—C12B—C8B—C7B3.9 (13)
C9A—C12A—C8A—O8A9.3 (11)C9B—C12B—C8B—C7B169.4 (7)
O8A—C8A—C7A—C6A178.4 (9)O8B—C8B—C7B—C6B179.7 (9)
C12A—C8A—C7A—C6A3.0 (14)C12B—C8B—C7B—C6B6.4 (14)
C8A—C7A—C6A—C5A3.3 (13)C8B—C7B—C6B—C5B5.4 (14)
C7A—C6A—C5A—C11A4.1 (13)C7B—C6B—C5B—C11B2.3 (14)
C8A—C12A—C11A—C5A4.2 (13)C6B—C5B—C11B—C12B0.1 (14)
C9A—C12A—C11A—C5A168.3 (9)C6B—C5B—C11B—C10B178.6 (7)
C8A—C12A—C11A—C10A176.4 (8)C8B—C12B—C11B—C5B0.7 (13)
C9A—C12A—C11A—C10A3.9 (14)C9B—C12B—C11B—C5B172.2 (9)
C6A—C5A—C11A—C12A4.5 (13)C8B—C12B—C11B—C10B177.8 (8)
C6A—C5A—C11A—C10A177.0 (8)C9B—C12B—C11B—C10B9.3 (13)
C14A—C10A—C11A—C12A11.0 (13)C24B—C10B—C11B—C5B49.7 (10)
C24A—C10A—C11A—C12A133.9 (10)C23B—C10B—C11B—C5B69.6 (11)
C23A—C10A—C11A—C12A106.9 (10)C14B—C10B—C11B—C5B172.5 (7)
C14A—C10A—C11A—C5A176.7 (8)C24B—C10B—C11B—C12B128.9 (8)
C24A—C10A—C11A—C5A53.8 (11)C23B—C10B—C11B—C12B111.9 (9)
C23A—C10A—C11A—C5A65.4 (11)C14B—C10B—C11B—C12B6.1 (11)
C7A—C8A—O8A—C15A5.6 (14)C12B—C8B—O8B—C15B168.1 (8)
C12A—C8A—O8A—C15A175.7 (8)C7B—C8B—O8B—C15B18.1 (13)
C8A—O8A—C15A—C16A171.9 (8)C8B—O8B—C15B—C16B159.1 (8)
O8A—C15A—C16A—O16A63.0 (12)O8B—C15B—C16B—O16B72.0 (9)
C15A—C16A—O16A—C17A167.3 (9)C15B—C16B—O16B—C17B163.6 (8)
C16A—O16A—C17A—C18A79.0 (12)C16B—O16B—C17B—C18B78.3 (11)
O16A—C17A—C18A—O18A63.9 (11)O16B—C17B—C18B—O18B61.1 (12)
C17A—C18A—O18A—C19A177.6 (9)C17B—C18B—O18B—C19B176.6 (7)
C18A—O18A—C19A—C20A178.1 (8)C18B—O18B—C19B—C20B179.3 (9)
O18A—C19A—C20A—O20A65.1 (13)O18B—C19B—C20B—O20B63.7 (12)
C19A—C20A—O20A—C21A69.1 (12)C19B—C20B—O20B—C21B72.5 (12)
C20A—O20A—C21A—C22A160.8 (8)C20B—O20B—C21B—C22B168.0 (9)
O20A—C21A—C22A—O1A73.4 (10)O20B—C21B—C22B—O1B81.6 (11)
C21A—C22A—O1A—C1A167.4 (8)C13B—C1B—O1B—C22B171.2 (9)
C2A—C1A—O1A—C22A11.0 (14)C2B—C1B—O1B—C22B8.4 (15)
C13A—C1A—O1A—C22A162.7 (9)C21B—C22B—O1B—C1B172.5 (8)

Experimental details

(xray)(neutron)
Crystal data
Chemical formulaC24H30O6·H2OC24H30O6·H2O
Mr432.50432.49
Crystal system, space groupMonoclinic, P21Monoclinic, P21
Temperature (K)29315
a, b, c (Å)12.845 (5), 14.575 (3), 13.779 (2)12.605 (5), 14.458 (3), 13.588 (2)
β (°) 117.72 (2) 117.12 (2)
V3)2283.6 (11)2204.1 (10)
Z44
Radiation typeCu Kα?, λ = 1.538 and 1.312 Å
µ (mm1)0.750.00
Crystal size (mm)0.35 × 0.25 × 0.202.5 × 1.6 × 0.2
Data collection
DiffractometerNonius CAD-4
diffractometer
D19 ILL ω
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
17753, 9092, 4804 1931, 1931, 1881
Rint0.0460.000
(sin θ/λ)max1)0.620
Distance from specimen to detector (mm)h = 1011, k = 013, l = 912
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.169, 0.91 0.046, 0.132, 0.78
No. of reflections90921881
No. of parameters605507
No. of restraints2171
(Δ/σ)max0.0780.123
Δρmax, Δρmin (e Å3)0.23, 0.260.06, 0.06
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter0.2 (4)10.0 (100)

Computer programs: CAD-4 EXPRESS88, RETREAT, SHELXS86 (Sheldrick, 1990), SHELXS86? (Sheldrick, 1990), SHELXL92 (Sheldrick, 1993), SHELXL92? (Sheldrick, 1993), SNOOPI.

 

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