Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100013032/qa0393sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013032/qa0393Isup2.hkl |
CCDC reference: 153945
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al.,1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: PLATON (Spek, 1998) and SHELXL97.
C22H32O6 | F(000) = 424 |
Mr = 392.48 | Dx = 1.313 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9870 (16) Å | Cell parameters from 3394 reflections |
b = 6.0330 (8) Å | θ = 1.9–27.5° |
c = 15.429 (3) Å | µ = 0.09 mm−1 |
β = 103.989 (6)° | T = 150 K |
V = 992.4 (3) Å3 | Needle, colourless |
Z = 2 | 0.15 × 0.05 × 0.02 mm |
Enraf Nonius KappaCCD area-detector diffractometer | 3394 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 2168 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 1.9° |
φ and ω scans to fill Ewald sphere | h = −14→13 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −5→7 |
Tmin = 0.987, Tmax = 0.998 | l = −18→18 |
7295 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0484P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
3394 reflections | Δρmax = 0.21 e Å−3 |
268 parameters | Δρmin = −0.26 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1054 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 1.7 (16) |
Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
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 | 0.1111 (2) | 1.0909 (4) | 0.25661 (15) | 0.0333 (6) | |
O2 | −0.0723 (2) | 0.7328 (5) | 0.08201 (18) | 0.0338 (7) | |
H2 | −0.097 (5) | 0.831 (10) | 0.052 (3) | 0.074 (19)* | |
O3 | 0.0583 (3) | 1.1301 (5) | 0.10578 (17) | 0.0356 (6) | |
H3 | 0.112 (3) | 1.249 (8) | 0.113 (2) | 0.043 (12)* | |
O4 | 0.1339 (3) | 0.5287 (4) | 0.06129 (16) | 0.0335 (6) | |
H4 | 0.057 (4) | 0.572 (8) | 0.057 (3) | 0.057 (14)* | |
O5 | 0.2501 (2) | 0.6552 (5) | 0.45729 (15) | 0.0362 (7) | |
O6 | 0.3354 (2) | 0.3276 (5) | 0.50887 (17) | 0.0461 (7) | |
C1 | 0.1542 (3) | 0.5484 (7) | 0.3864 (2) | 0.0316 (9) | |
H1 | 0.1869 | 0.4031 | 0.3705 | 0.034 (2)* | |
C2 | 0.0430 (3) | 0.5085 (7) | 0.4252 (2) | 0.0343 (9) | |
H2A | 0.0210 | 0.6479 | 0.4516 | 0.034 (2)* | |
H2B | 0.0653 | 0.3968 | 0.4734 | 0.034 (2)* | |
C3 | −0.0700 (3) | 0.4272 (7) | 0.3542 (3) | 0.0354 (9) | |
H3A | −0.1398 | 0.3953 | 0.3826 | 0.034 (2)* | |
H3B | −0.0479 | 0.2875 | 0.3281 | 0.034 (2)* | |
C4 | −0.1131 (3) | 0.5974 (7) | 0.2800 (2) | 0.0326 (9) | |
C5 | 0.0008 (3) | 0.6505 (6) | 0.2400 (2) | 0.0283 (8) | |
H5 | 0.0149 | 0.5126 | 0.2078 | 0.034 (2)* | |
C6 | −0.0260 (3) | 0.8312 (6) | 0.1686 (2) | 0.0291 (8) | |
H6 | −0.0929 | 0.9300 | 0.1809 | 0.034 (2)* | |
C7 | 0.0907 (3) | 0.9705 (6) | 0.1736 (2) | 0.0298 (9) | |
C8 | 0.2091 (3) | 0.8381 (7) | 0.1716 (2) | 0.0306 (9) | |
C9 | 0.2298 (3) | 0.6652 (6) | 0.2495 (2) | 0.0284 (8) | |
H9 | 0.2130 | 0.5154 | 0.2214 | 0.034 (2)* | |
C10 | 0.1306 (3) | 0.7037 (6) | 0.3048 (2) | 0.0293 (9) | |
C11 | 0.3674 (3) | 0.6655 (7) | 0.3041 (2) | 0.0346 (9) | |
H11A | 0.3820 | 0.7991 | 0.3425 | 0.034 (2)* | |
H11B | 0.3816 | 0.5341 | 0.3437 | 0.034 (2)* | |
C12 | 0.4632 (3) | 0.6625 (7) | 0.2461 (3) | 0.0415 (10) | |
H12A | 0.4737 | 0.5085 | 0.2269 | 0.034 (2)* | |
H12B | 0.5454 | 0.7145 | 0.2820 | 0.034 (2)* | |
C13 | 0.4206 (3) | 0.8128 (8) | 0.1623 (2) | 0.0405 (10) | |
H13 | 0.4937 | 0.8854 | 0.1458 | 0.034 (2)* | |
C14 | 0.3257 (3) | 0.9849 (7) | 0.1797 (3) | 0.0365 (9) | |
H14A | 0.3534 | 1.0512 | 0.2399 | 0.034 (2)* | |
H14B | 0.3108 | 1.1041 | 0.1342 | 0.034 (2)* | |
C15 | 0.2059 (4) | 0.7275 (7) | 0.0806 (3) | 0.0364 (10) | |
H15 | 0.1739 | 0.8373 | 0.0319 | 0.034 (2)* | |
C16 | 0.3427 (4) | 0.6803 (7) | 0.0852 (3) | 0.0399 (10) | |
C17 | 0.3851 (4) | 0.5429 (8) | 0.0328 (3) | 0.0569 (13) | |
H17A | 0.3278 | 0.4635 | −0.0127 | 0.034 (2)* | |
H17B | 0.4728 | 0.5234 | 0.0404 | 0.034 (2)* | |
C18 | −0.2165 (3) | 0.4924 (7) | 0.2065 (3) | 0.0388 (10) | |
H18A | −0.2450 | 0.5997 | 0.1581 | 0.063 (4)* | |
H18B | −0.2871 | 0.4498 | 0.2313 | 0.063 (4)* | |
H18C | −0.1832 | 0.3607 | 0.1830 | 0.063 (4)* | |
C19 | −0.1700 (3) | 0.8005 (7) | 0.3168 (2) | 0.0391 (10) | |
H19A | −0.1970 | 0.9097 | 0.2690 | 0.063 (4)* | |
H19B | −0.1067 | 0.8670 | 0.3657 | 0.063 (4)* | |
H19C | −0.2423 | 0.7535 | 0.3390 | 0.063 (4)* | |
C20 | 0.1412 (3) | 0.9457 (6) | 0.3338 (2) | 0.0326 (9) | |
H20A | 0.0830 | 0.9751 | 0.3725 | 0.034 (2)* | |
H20B | 0.2276 | 0.9762 | 0.3689 | 0.034 (2)* | |
C21 | 0.3326 (3) | 0.5256 (8) | 0.5142 (2) | 0.0379 (10) | |
C22 | 0.4189 (4) | 0.6643 (8) | 0.5830 (3) | 0.0502 (12) | |
H22A | 0.5033 | 0.6608 | 0.5724 | 0.063 (4)* | |
H22B | 0.4215 | 0.6054 | 0.6426 | 0.063 (4)* | |
H22C | 0.3883 | 0.8174 | 0.5790 | 0.063 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0458 (15) | 0.0243 (15) | 0.0276 (14) | 0.0004 (12) | 0.0045 (11) | −0.0015 (11) |
O2 | 0.0390 (15) | 0.0308 (16) | 0.0278 (15) | −0.0034 (13) | 0.0007 (12) | −0.0009 (13) |
O3 | 0.0453 (15) | 0.0249 (15) | 0.0327 (14) | −0.0025 (13) | 0.0017 (11) | 0.0061 (13) |
O4 | 0.0350 (15) | 0.0281 (15) | 0.0361 (15) | −0.0027 (13) | 0.0062 (12) | −0.0013 (12) |
O5 | 0.0396 (14) | 0.0337 (16) | 0.0306 (14) | 0.0012 (13) | −0.0005 (11) | 0.0024 (13) |
O6 | 0.0523 (17) | 0.0378 (18) | 0.0436 (17) | 0.0069 (14) | 0.0027 (13) | 0.0076 (15) |
C1 | 0.0364 (19) | 0.027 (2) | 0.028 (2) | −0.0019 (18) | 0.0023 (16) | 0.0049 (17) |
C2 | 0.040 (2) | 0.033 (2) | 0.030 (2) | 0.0018 (18) | 0.0088 (16) | 0.0040 (18) |
C3 | 0.038 (2) | 0.029 (2) | 0.041 (2) | −0.0001 (19) | 0.0133 (17) | 0.0011 (19) |
C4 | 0.0308 (19) | 0.032 (2) | 0.035 (2) | 0.0002 (17) | 0.0082 (16) | −0.0002 (18) |
C5 | 0.0316 (19) | 0.0244 (19) | 0.0261 (18) | 0.0009 (17) | 0.0018 (15) | −0.0002 (17) |
C6 | 0.0297 (17) | 0.026 (2) | 0.029 (2) | −0.0022 (17) | 0.0019 (14) | 0.0007 (17) |
C7 | 0.040 (2) | 0.021 (2) | 0.026 (2) | 0.0013 (17) | 0.0015 (16) | −0.0003 (16) |
C8 | 0.0330 (19) | 0.026 (2) | 0.030 (2) | −0.0022 (17) | 0.0028 (15) | 0.0015 (18) |
C9 | 0.0287 (18) | 0.0246 (19) | 0.031 (2) | 0.0006 (17) | 0.0052 (15) | 0.0028 (17) |
C10 | 0.033 (2) | 0.030 (2) | 0.0231 (18) | 0.0020 (17) | 0.0029 (15) | 0.0035 (16) |
C11 | 0.0298 (18) | 0.036 (2) | 0.035 (2) | 0.0025 (18) | 0.0017 (16) | −0.0008 (19) |
C12 | 0.0326 (19) | 0.044 (3) | 0.044 (2) | 0.001 (2) | 0.0033 (17) | 0.000 (2) |
C13 | 0.037 (2) | 0.045 (3) | 0.041 (2) | −0.009 (2) | 0.0120 (17) | −0.001 (2) |
C14 | 0.042 (2) | 0.034 (2) | 0.034 (2) | −0.0068 (19) | 0.0102 (17) | 0.0000 (19) |
C15 | 0.044 (2) | 0.030 (2) | 0.033 (2) | −0.0042 (18) | 0.0046 (17) | −0.0034 (18) |
C16 | 0.039 (2) | 0.041 (3) | 0.042 (2) | −0.005 (2) | 0.0135 (18) | −0.001 (2) |
C17 | 0.044 (2) | 0.069 (3) | 0.058 (3) | 0.006 (3) | 0.013 (2) | −0.022 (3) |
C18 | 0.0314 (19) | 0.038 (3) | 0.046 (2) | −0.0070 (19) | 0.0071 (17) | −0.001 (2) |
C19 | 0.038 (2) | 0.039 (2) | 0.041 (2) | 0.0056 (19) | 0.0092 (17) | 0.002 (2) |
C20 | 0.0372 (19) | 0.028 (2) | 0.030 (2) | 0.0039 (18) | 0.0033 (16) | 0.0059 (18) |
C21 | 0.036 (2) | 0.044 (3) | 0.035 (2) | 0.000 (2) | 0.0090 (17) | 0.009 (2) |
C22 | 0.046 (2) | 0.055 (3) | 0.041 (2) | −0.007 (2) | −0.0072 (19) | 0.004 (2) |
O1—C7 | 1.442 (4) | C9—C11 | 1.543 (4) |
O1—C20 | 1.451 (4) | C9—C10 | 1.556 (5) |
O2—C6 | 1.438 (4) | C9—H9 | 1.0000 |
O2—H2 | 0.76 (5) | C10—C20 | 1.523 (5) |
O3—C7 | 1.403 (4) | C11—C12 | 1.537 (5) |
O3—H3 | 0.92 (4) | C11—H11A | 0.9900 |
O4—C15 | 1.428 (4) | C11—H11B | 0.9900 |
O4—H4 | 0.87 (4) | C12—C13 | 1.557 (6) |
O5—C21 | 1.349 (5) | C12—H12A | 0.9900 |
O5—C1 | 1.471 (4) | C12—H12B | 0.9900 |
O6—C21 | 1.198 (5) | C13—C16 | 1.515 (6) |
C1—C2 | 1.504 (5) | C13—C14 | 1.540 (6) |
C1—C10 | 1.540 (5) | C13—H13 | 1.0000 |
C1—H1 | 1.0000 | C14—H14A | 0.9900 |
C2—C3 | 1.524 (5) | C14—H14B | 0.9900 |
C2—H2A | 0.9900 | C15—C16 | 1.515 (6) |
C2—H2B | 0.9900 | C15—H15 | 1.0000 |
C3—C4 | 1.526 (5) | C16—C17 | 1.319 (6) |
C3—H3A | 0.9900 | C17—H17A | 0.9500 |
C3—H3B | 0.9900 | C17—H17B | 0.9500 |
C4—C18 | 1.535 (5) | C18—H18A | 0.9800 |
C4—C19 | 1.544 (5) | C18—H18B | 0.9800 |
C4—C5 | 1.557 (5) | C18—H18C | 0.9800 |
C5—C6 | 1.527 (5) | C19—H19A | 0.9800 |
C5—C10 | 1.564 (5) | C19—H19B | 0.9800 |
C5—H5 | 1.0000 | C19—H19C | 0.9800 |
C6—C7 | 1.519 (5) | C20—H20A | 0.9900 |
C6—H6 | 1.0000 | C20—H20B | 0.9900 |
C7—C8 | 1.533 (5) | C21—C22 | 1.496 (6) |
C8—C14 | 1.538 (5) | C22—H22A | 0.9800 |
C8—C15 | 1.547 (5) | C22—H22B | 0.9800 |
C8—C9 | 1.566 (5) | C22—H22C | 0.9800 |
C7—O1—C20 | 112.4 (3) | C9—C10—C5 | 105.7 (3) |
C6—O2—H2 | 104 (4) | C12—C11—C9 | 113.6 (3) |
C7—O3—H3 | 114 (2) | C12—C11—H11A | 108.8 |
C15—O4—H4 | 104 (3) | C9—C11—H11A | 108.8 |
C21—O5—C1 | 118.5 (3) | C12—C11—H11B | 108.8 |
O5—C1—C2 | 106.2 (3) | C9—C11—H11B | 108.8 |
O5—C1—C10 | 106.9 (3) | H11A—C11—H11B | 107.7 |
C2—C1—C10 | 115.4 (3) | C11—C12—C13 | 111.5 (3) |
O5—C1—H1 | 109.4 | C11—C12—H12A | 109.3 |
C2—C1—H1 | 109.4 | C13—C12—H12A | 109.3 |
C10—C1—H1 | 109.4 | C11—C12—H12B | 109.3 |
C1—C2—C3 | 111.4 (3) | C13—C12—H12B | 109.3 |
C1—C2—H2A | 109.3 | H12A—C12—H12B | 108.0 |
C3—C2—H2A | 109.3 | C16—C13—C14 | 102.4 (3) |
C1—C2—H2B | 109.3 | C16—C13—C12 | 110.1 (4) |
C3—C2—H2B | 109.3 | C14—C13—C12 | 109.1 (3) |
H2A—C2—H2B | 108.0 | C16—C13—H13 | 111.6 |
C2—C3—C4 | 111.9 (3) | C14—C13—H13 | 111.6 |
C2—C3—H3A | 109.2 | C12—C13—H13 | 111.6 |
C4—C3—H3A | 109.2 | C8—C14—C13 | 100.6 (3) |
C2—C3—H3B | 109.2 | C8—C14—H14A | 111.7 |
C4—C3—H3B | 109.2 | C13—C14—H14A | 111.7 |
H3A—C3—H3B | 107.9 | C8—C14—H14B | 111.7 |
C3—C4—C18 | 108.5 (3) | C13—C14—H14B | 111.7 |
C3—C4—C19 | 109.8 (3) | H14A—C14—H14B | 109.4 |
C18—C4—C19 | 107.9 (3) | O4—C15—C16 | 110.2 (3) |
C3—C4—C5 | 107.6 (3) | O4—C15—C8 | 116.2 (3) |
C18—C4—C5 | 108.3 (3) | C16—C15—C8 | 103.5 (3) |
C19—C4—C5 | 114.7 (3) | O4—C15—H15 | 108.9 |
C6—C5—C4 | 113.6 (3) | C16—C15—H15 | 108.9 |
C6—C5—C10 | 107.6 (3) | C8—C15—H15 | 108.9 |
C4—C5—C10 | 119.0 (3) | C17—C16—C15 | 125.7 (4) |
C6—C5—H5 | 105.2 | C17—C16—C13 | 126.6 (4) |
C4—C5—H5 | 105.2 | C15—C16—C13 | 107.7 (3) |
C10—C5—H5 | 105.2 | C16—C17—H17A | 120.0 |
O2—C6—C7 | 112.3 (3) | C16—C17—H17B | 120.0 |
O2—C6—C5 | 109.8 (3) | H17A—C17—H17B | 120.0 |
C7—C6—C5 | 110.2 (3) | C4—C18—H18A | 109.5 |
O2—C6—H6 | 108.1 | C4—C18—H18B | 109.5 |
C7—C6—H6 | 108.1 | H18A—C18—H18B | 109.5 |
C5—C6—H6 | 108.1 | C4—C18—H18C | 109.5 |
O3—C7—O1 | 105.9 (3) | H18A—C18—H18C | 109.5 |
O3—C7—C6 | 106.5 (3) | H18B—C18—H18C | 109.5 |
O1—C7—C6 | 105.8 (3) | C4—C19—H19A | 109.5 |
O3—C7—C8 | 114.0 (3) | C4—C19—H19B | 109.5 |
O1—C7—C8 | 109.2 (3) | H19A—C19—H19B | 109.5 |
C6—C7—C8 | 114.9 (3) | C4—C19—H19C | 109.5 |
C7—C8—C14 | 113.1 (3) | H19A—C19—H19C | 109.5 |
C7—C8—C15 | 114.2 (3) | H19B—C19—H19C | 109.5 |
C14—C8—C15 | 99.1 (3) | O1—C20—C10 | 110.6 (3) |
C7—C8—C9 | 107.4 (3) | O1—C20—H20A | 109.5 |
C14—C8—C9 | 111.0 (3) | C10—C20—H20A | 109.5 |
C15—C8—C9 | 112.1 (3) | O1—C20—H20B | 109.5 |
C11—C9—C10 | 115.1 (3) | C10—C20—H20B | 109.5 |
C11—C9—C8 | 111.1 (3) | H20A—C20—H20B | 108.1 |
C10—C9—C8 | 109.3 (3) | O6—C21—O5 | 123.9 (4) |
C11—C9—H9 | 107.0 | O6—C21—C22 | 125.7 (4) |
C10—C9—H9 | 107.0 | O5—C21—C22 | 110.4 (4) |
C8—C9—H9 | 107.0 | C21—C22—H22A | 109.5 |
C20—C10—C1 | 110.9 (3) | C21—C22—H22B | 109.5 |
C20—C10—C9 | 106.9 (3) | H22A—C22—H22B | 109.5 |
C1—C10—C9 | 110.8 (3) | C21—C22—H22C | 109.5 |
C20—C10—C5 | 112.2 (3) | H22A—C22—H22C | 109.5 |
C1—C10—C5 | 110.2 (3) | H22B—C22—H22C | 109.5 |
C21—O5—C1—C2 | 89.9 (4) | C2—C1—C10—C9 | −158.6 (3) |
C21—O5—C1—C10 | −146.4 (3) | O5—C1—C10—C5 | −159.9 (3) |
O5—C1—C2—C3 | 172.1 (3) | C2—C1—C10—C5 | −42.0 (4) |
C10—C1—C2—C3 | 53.9 (5) | C11—C9—C10—C20 | 71.1 (4) |
C1—C2—C3—C4 | −61.8 (4) | C8—C9—C10—C20 | −54.7 (4) |
C2—C3—C4—C18 | 173.4 (3) | C11—C9—C10—C1 | −49.8 (4) |
C2—C3—C4—C19 | −68.9 (4) | C8—C9—C10—C1 | −175.6 (3) |
C2—C3—C4—C5 | 56.5 (4) | C11—C9—C10—C5 | −169.2 (3) |
C3—C4—C5—C6 | −176.1 (3) | C8—C9—C10—C5 | 65.0 (4) |
C18—C4—C5—C6 | 66.8 (4) | C6—C5—C10—C20 | 47.3 (4) |
C19—C4—C5—C6 | −53.7 (4) | C4—C5—C10—C20 | −83.6 (4) |
C3—C4—C5—C10 | −48.0 (4) | C6—C5—C10—C1 | 171.4 (3) |
C18—C4—C5—C10 | −165.1 (3) | C4—C5—C10—C1 | 40.6 (5) |
C19—C4—C5—C10 | 74.5 (4) | C6—C5—C10—C9 | −68.8 (4) |
C4—C5—C6—O2 | −90.7 (4) | C4—C5—C10—C9 | 160.3 (3) |
C10—C5—C6—O2 | 135.5 (3) | C10—C9—C11—C12 | −171.2 (3) |
C4—C5—C6—C7 | 145.1 (3) | C8—C9—C11—C12 | −46.3 (4) |
C10—C5—C6—C7 | 11.3 (4) | C9—C11—C12—C13 | 39.5 (5) |
C20—O1—C7—O3 | 177.8 (3) | C11—C12—C13—C16 | −90.0 (4) |
C20—O1—C7—C6 | 65.1 (3) | C11—C12—C13—C14 | 21.7 (4) |
C20—O1—C7—C8 | −59.0 (4) | C7—C8—C14—C13 | −172.3 (3) |
O2—C6—C7—O3 | 56.8 (4) | C15—C8—C14—C13 | −51.1 (3) |
C5—C6—C7—O3 | 179.5 (3) | C9—C8—C14—C13 | 66.9 (4) |
O2—C6—C7—O1 | 169.1 (3) | C16—C13—C14—C8 | 42.4 (4) |
C5—C6—C7—O1 | −68.1 (4) | C12—C13—C14—C8 | −74.3 (3) |
O2—C6—C7—C8 | −70.4 (4) | C7—C8—C15—O4 | −78.1 (4) |
C5—C6—C7—C8 | 52.4 (4) | C14—C8—C15—O4 | 161.4 (3) |
O3—C7—C8—C14 | 58.6 (4) | C9—C8—C15—O4 | 44.3 (4) |
O1—C7—C8—C14 | −59.6 (4) | C7—C8—C15—C16 | 161.0 (3) |
C6—C7—C8—C14 | −178.2 (3) | C14—C8—C15—C16 | 40.5 (4) |
O3—C7—C8—C15 | −53.7 (4) | C9—C8—C15—C16 | −76.7 (4) |
O1—C7—C8—C15 | −171.9 (3) | O4—C15—C16—C17 | 38.5 (6) |
C6—C7—C8—C15 | 69.5 (4) | C8—C15—C16—C17 | 163.4 (5) |
O3—C7—C8—C9 | −178.7 (3) | O4—C15—C16—C13 | −139.7 (3) |
O1—C7—C8—C9 | 63.1 (4) | C8—C15—C16—C13 | −14.8 (4) |
C6—C7—C8—C9 | −55.4 (4) | C14—C13—C16—C17 | 164.8 (5) |
C7—C8—C9—C11 | −132.9 (3) | C12—C13—C16—C17 | −79.2 (5) |
C14—C8—C9—C11 | −8.8 (4) | C14—C13—C16—C15 | −17.0 (4) |
C15—C8—C9—C11 | 101.0 (4) | C12—C13—C16—C15 | 99.0 (4) |
C7—C8—C9—C10 | −4.7 (4) | C7—O1—C20—C10 | −5.3 (4) |
C14—C8—C9—C10 | 119.4 (3) | C1—C10—C20—O1 | −176.5 (3) |
C15—C8—C9—C10 | −130.9 (3) | C9—C10—C20—O1 | 62.6 (3) |
O5—C1—C10—C20 | −35.0 (4) | C5—C10—C20—O1 | −52.7 (4) |
C2—C1—C10—C20 | 82.9 (4) | C1—O5—C21—O6 | 2.5 (6) |
O5—C1—C10—C9 | 83.5 (3) | C1—O5—C21—C22 | −177.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O4i | 0.76 (6) | 2.07 (5) | 2.795 (4) | 158 (5) |
O3—H3···O4ii | 0.92 (4) | 1.91 (5) | 2.687 (4) | 142 (3) |
O4—H4···O2 | 0.87 (5) | 1.84 (5) | 2.665 (5) | 158 (4) |
Symmetry codes: (i) −x, y+1/2, −z; (ii) x, y+1, z. |