The title compound, 10,13-deacetyl-
abeo-baccatin IV, C
28H
40O
12, crystallized in space group
P1. The molecular structure shows that the
B/
C ring junction is
trans-fused, while the
A ring is in a
syn conformation with respect to the
C ring and
anti with respect to the
D ring. The conformations of the individual rings differ from each other. The molecule as a whole adopts a cage-type folded conformation. Intra- and intermolecular O—H
O and C—H
O hydrogen bonds, together with van der Waals interactions, stabilize the crystal structure.
Supporting information
CCDC reference: 177201
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.038
- wR factor = 0.105
- Data-to-parameter ratio = 8.2
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _reflns_number_total 3060
Count of symmetry unique reflns 2594
Completeness (_total/calc) 117.96%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 466
Fraction of Friedel pairs measured 0.180
Are heavy atom types Z>Si present no
ALERT: MoKa measured Friedel data cannot be used to
determine absolute structure in a light-atom
study EXCEPT under VERY special conditions.
It is preferred that Friedel data is merged in such cases.
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-NT (Bruker, 1997); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.
10,13-Deacetyl
abeo-baccatin IV
top
Crystal data top
C28H40O12 | F(000) = 304 |
Mr = 568.60 | Dx = 1.282 Mg m−3 |
Triclinic, P1 | Melting point = 220–222 K |
a = 8.957 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.667 (1) Å | Cell parameters from 26 reflections |
c = 9.827 (1) Å | θ = 5.0–9.2° |
α = 110.10 (1)° | µ = 0.10 mm−1 |
β = 92.42 (1)° | T = 293 K |
γ = 110.39 (1)° | Block, colourless |
V = 736.2 (1) Å3 | 0.48 × 0.35 × 0.33 mm |
Z = 1 | |
Data collection top
Bruker P4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.3° |
Graphite monochromator | h = −10→1 |
θ–\2q scans | k = −10→10 |
3060 measured reflections | l = −11→11 |
3060 independent reflections | 3 standard reflections every 97 reflections |
2941 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0759P)2 + 0.0885P] where P = (Fo2 + 2Fc2)/3 |
3060 reflections | (Δ/σ)max = 0.002 |
372 parameters | Δρmax = 0.18 e Å−3 |
3 restraints | Δρmin = −0.18 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.4706 (3) | 0.3094 (3) | 0.9555 (2) | 0.0310 (5) | |
C2 | 0.4771 (3) | 0.3588 (3) | 0.8189 (3) | 0.0314 (5) | |
H2 | 0.5046 | 0.2836 | 0.7385 | 0.038* | |
C3 | 0.3117 (3) | 0.3586 (3) | 0.7666 (2) | 0.0297 (5) | |
H3 | 0.2543 | 0.3579 | 0.8492 | 0.036* | |
C4 | 0.3161 (3) | 0.5095 (3) | 0.7420 (3) | 0.0346 (5) | |
C5 | 0.1676 (4) | 0.4928 (4) | 0.6424 (3) | 0.0425 (6) | |
H5 | 0.1344 | 0.5825 | 0.6863 | 0.051* | |
C6 | 0.0222 (4) | 0.3352 (4) | 0.5814 (3) | 0.0474 (7) | |
H6A | 0.0045 | 0.2966 | 0.4747 | 0.057* | |
H6B | −0.0725 | 0.3549 | 0.6122 | 0.057* | |
C7 | 0.0343 (3) | 0.2029 (3) | 0.6274 (3) | 0.0353 (5) | |
H7A | 0.0037 | 0.2184 | 0.7245 | 0.042* | |
C8 | 0.2042 (3) | 0.1978 (3) | 0.6355 (2) | 0.0308 (5) | |
C9 | 0.2163 (3) | 0.0576 (3) | 0.6727 (2) | 0.0314 (5) | |
H9 | 0.3234 | 0.0560 | 0.6588 | 0.038* | |
C10 | 0.1920 (3) | 0.0506 (3) | 0.8235 (3) | 0.0324 (5) | |
H10 | 0.0790 | 0.0353 | 0.8309 | 0.039* | |
C11 | 0.2976 (3) | 0.2005 (3) | 0.9530 (3) | 0.0302 (5) | |
C12 | 0.2484 (3) | 0.2517 (3) | 1.0806 (3) | 0.0370 (6) | |
C13 | 0.3747 (4) | 0.4037 (3) | 1.1901 (3) | 0.0408 (6) | |
H13 | 0.4229 | 0.3840 | 1.2695 | 0.049* | |
C14 | 0.4990 (3) | 0.4557 (3) | 1.0993 (3) | 0.0388 (6) | |
H14A | 0.6075 | 0.4941 | 1.1542 | 0.047* | |
H14B | 0.4874 | 0.5415 | 1.0758 | 0.047* | |
C15 | 0.5949 (3) | 0.2308 (3) | 0.9648 (3) | 0.0378 (6) | |
C16 | 0.6018 (4) | 0.1958 (5) | 1.1049 (4) | 0.0564 (8) | |
H17A | 0.4947 | 0.1329 | 1.1117 | 0.085* | |
H17B | 0.6445 | 0.2945 | 1.1894 | 0.085* | |
H17C | 0.6706 | 0.1379 | 1.1013 | 0.085* | |
C17 | 0.7670 (4) | 0.3294 (4) | 0.9549 (4) | 0.0480 (7) | |
H16A | 0.8386 | 0.2794 | 0.9695 | 0.072* | |
H16B | 0.8030 | 0.4351 | 1.0296 | 0.072* | |
H16C | 0.7674 | 0.3356 | 0.8595 | 0.072* | |
C18 | 0.7127 (4) | 0.5467 (4) | 0.7772 (4) | 0.0498 (7) | |
C19 | 0.8344 (5) | 0.7153 (5) | 0.8483 (6) | 0.0786 (12) | |
H21A | 0.8952 | 0.7286 | 0.9379 | 0.118* | |
H21B | 0.7792 | 0.7873 | 0.8701 | 0.118* | |
H21C | 0.9067 | 0.7378 | 0.7823 | 0.118* | |
C20 | 0.2437 (4) | 0.6463 (3) | 0.9656 (3) | 0.0438 (7) | |
C21 | 0.3030 (6) | 0.7896 (4) | 1.1061 (4) | 0.0648 (10) | |
H25A | 0.2340 | 0.8477 | 1.1133 | 0.097* | |
H25B | 0.4117 | 0.8570 | 1.1076 | 0.097* | |
H25C | 0.3017 | 0.7566 | 1.1878 | 0.097* | |
C22 | 0.4138 (4) | 0.5648 (4) | 0.6339 (3) | 0.0484 (7) | |
H20A | 0.4775 | 0.6788 | 0.6725 | 0.058* | |
H20B | 0.4806 | 0.5054 | 0.5950 | 0.058* | |
C23 | −0.2092 (4) | −0.0311 (4) | 0.5655 (4) | 0.0528 (8) | |
C24 | −0.3291 (5) | −0.1710 (5) | 0.4396 (5) | 0.0833 (13) | |
H27A | −0.3177 | −0.2671 | 0.4365 | 0.125* | |
H27B | −0.3098 | −0.1571 | 0.3489 | 0.125* | |
H27C | −0.4369 | −0.1784 | 0.4526 | 0.125* | |
C25 | 0.2628 (4) | 0.1797 (3) | 0.4871 (3) | 0.0409 (6) | |
H19A | 0.1968 | 0.0764 | 0.4141 | 0.061* | |
H19B | 0.3737 | 0.1901 | 0.4989 | 0.061* | |
H19C | 0.2545 | 0.2612 | 0.4563 | 0.061* | |
C26 | 0.1500 (4) | −0.1991 (3) | 0.4818 (3) | 0.0441 (6) | |
C27 | 0.0095 (5) | −0.3495 (4) | 0.3884 (5) | 0.0721 (11) | |
H29A | 0.0490 | −0.4239 | 0.3246 | 0.108* | |
H29B | −0.0587 | −0.3251 | 0.3301 | 0.108* | |
H29C | −0.0517 | −0.3957 | 0.4508 | 0.108* | |
C28 | 0.0882 (4) | 0.1745 (4) | 1.1199 (3) | 0.0512 (7) | |
H18A | 0.0075 | 0.1115 | 1.0317 | 0.077* | |
H18B | 0.0567 | 0.2557 | 1.1839 | 0.077* | |
H18C | 0.0981 | 0.1070 | 1.1691 | 0.077* | |
O1 | 0.5347 (2) | 0.0795 (2) | 0.8403 (2) | 0.0478 (5) | |
H1 | 0.6113 | 0.0580 | 0.8108 | 0.072* | |
O2 | 0.6036 (2) | 0.5175 (2) | 0.8644 (2) | 0.0393 (4) | |
O3 | 0.3609 (2) | 0.6414 (2) | 0.88414 (19) | 0.0397 (4) | |
O4 | 0.2670 (3) | 0.5169 (3) | 0.5315 (2) | 0.0563 (6) | |
O5 | −0.0883 (2) | 0.0576 (2) | 0.5191 (2) | 0.0446 (5) | |
O6 | 0.0971 (2) | −0.0913 (2) | 0.56713 (19) | 0.0388 (4) | |
O7 | 0.2133 (2) | −0.0868 (2) | 0.8286 (2) | 0.0423 (4) | |
H7 | 0.3094 | −0.0727 | 0.8328 | 0.064* | |
O8 | 0.3114 (3) | 0.5236 (3) | 1.2485 (2) | 0.0570 (6) | |
H8 | 0.3216 | 0.5507 | 1.3383 | 0.086* | |
O9 | 0.7123 (3) | 0.4513 (3) | 0.6615 (3) | 0.0636 (6) | |
O10 | 0.1081 (3) | 0.5448 (3) | 0.9266 (2) | 0.0549 (5) | |
O11 | −0.2191 (3) | −0.0044 (3) | 0.6934 (3) | 0.0669 (7) | |
O12 | 0.2885 (3) | −0.1777 (3) | 0.4786 (3) | 0.0661 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0275 (12) | 0.0278 (11) | 0.0302 (11) | 0.0050 (10) | 0.0032 (9) | 0.0084 (9) |
C2 | 0.0269 (12) | 0.0279 (11) | 0.0342 (11) | 0.0049 (10) | 0.0087 (10) | 0.0112 (9) |
C3 | 0.0268 (12) | 0.0310 (11) | 0.0320 (11) | 0.0096 (10) | 0.0111 (9) | 0.0139 (9) |
C4 | 0.0364 (14) | 0.0348 (12) | 0.0337 (12) | 0.0139 (11) | 0.0108 (10) | 0.0135 (10) |
C5 | 0.0482 (16) | 0.0504 (16) | 0.0413 (13) | 0.0267 (14) | 0.0149 (12) | 0.0234 (12) |
C6 | 0.0449 (17) | 0.0545 (17) | 0.0460 (14) | 0.0266 (14) | 0.0042 (13) | 0.0160 (12) |
C7 | 0.0304 (13) | 0.0388 (13) | 0.0322 (11) | 0.0131 (11) | 0.0043 (10) | 0.0087 (10) |
C8 | 0.0323 (12) | 0.0318 (11) | 0.0270 (11) | 0.0126 (10) | 0.0070 (9) | 0.0093 (9) |
C9 | 0.0277 (12) | 0.0305 (12) | 0.0313 (11) | 0.0110 (10) | 0.0063 (9) | 0.0065 (9) |
C10 | 0.0270 (12) | 0.0280 (11) | 0.0374 (12) | 0.0061 (10) | 0.0059 (10) | 0.0115 (10) |
C11 | 0.0285 (12) | 0.0311 (11) | 0.0312 (11) | 0.0102 (10) | 0.0056 (9) | 0.0135 (9) |
C12 | 0.0382 (14) | 0.0431 (13) | 0.0316 (11) | 0.0138 (12) | 0.0100 (10) | 0.0181 (10) |
C13 | 0.0441 (15) | 0.0451 (14) | 0.0295 (11) | 0.0155 (12) | 0.0074 (11) | 0.0117 (10) |
C14 | 0.0390 (14) | 0.0336 (13) | 0.0313 (11) | 0.0057 (11) | 0.0027 (10) | 0.0069 (10) |
C15 | 0.0306 (13) | 0.0362 (13) | 0.0430 (13) | 0.0096 (11) | 0.0034 (11) | 0.0147 (11) |
C16 | 0.0472 (18) | 0.0664 (19) | 0.068 (2) | 0.0236 (16) | 0.0082 (15) | 0.0383 (17) |
C17 | 0.0299 (14) | 0.0473 (15) | 0.0664 (18) | 0.0137 (13) | 0.0064 (13) | 0.0230 (13) |
C18 | 0.0342 (15) | 0.0528 (17) | 0.074 (2) | 0.0162 (13) | 0.0234 (14) | 0.0369 (16) |
C19 | 0.045 (2) | 0.058 (2) | 0.123 (4) | −0.0017 (18) | 0.023 (2) | 0.046 (2) |
C20 | 0.0575 (19) | 0.0406 (15) | 0.0431 (14) | 0.0256 (15) | 0.0185 (13) | 0.0195 (12) |
C21 | 0.094 (3) | 0.0456 (17) | 0.0492 (16) | 0.0267 (19) | 0.0216 (18) | 0.0106 (14) |
C22 | 0.0514 (18) | 0.0545 (17) | 0.0515 (16) | 0.0220 (14) | 0.0226 (14) | 0.0314 (14) |
C23 | 0.0294 (15) | 0.0505 (16) | 0.0639 (19) | 0.0132 (13) | 0.0067 (13) | 0.0076 (14) |
C24 | 0.045 (2) | 0.073 (3) | 0.087 (3) | 0.0021 (19) | 0.000 (2) | 0.002 (2) |
C25 | 0.0479 (16) | 0.0447 (14) | 0.0332 (12) | 0.0209 (13) | 0.0140 (11) | 0.0147 (10) |
C26 | 0.0456 (17) | 0.0372 (14) | 0.0415 (13) | 0.0193 (13) | 0.0024 (12) | 0.0031 (11) |
C27 | 0.065 (2) | 0.0461 (18) | 0.074 (2) | 0.0228 (18) | −0.0151 (19) | −0.0102 (16) |
C28 | 0.0448 (17) | 0.0653 (18) | 0.0387 (14) | 0.0137 (15) | 0.0174 (13) | 0.0208 (13) |
O1 | 0.0356 (10) | 0.0360 (9) | 0.0642 (12) | 0.0142 (8) | 0.0079 (9) | 0.0101 (9) |
O2 | 0.0290 (9) | 0.0319 (9) | 0.0487 (10) | 0.0041 (8) | 0.0114 (8) | 0.0130 (8) |
O3 | 0.0436 (11) | 0.0311 (9) | 0.0408 (9) | 0.0103 (8) | 0.0125 (8) | 0.0131 (7) |
O4 | 0.0678 (15) | 0.0748 (15) | 0.0481 (11) | 0.0361 (13) | 0.0226 (11) | 0.0389 (11) |
O5 | 0.0342 (10) | 0.0504 (11) | 0.0388 (9) | 0.0145 (9) | 0.0006 (8) | 0.0075 (8) |
O6 | 0.0333 (10) | 0.0331 (9) | 0.0370 (9) | 0.0105 (8) | 0.0014 (7) | 0.0013 (7) |
O7 | 0.0406 (11) | 0.0316 (9) | 0.0513 (10) | 0.0083 (8) | 0.0087 (9) | 0.0176 (8) |
O8 | 0.0788 (17) | 0.0517 (12) | 0.0379 (10) | 0.0291 (12) | 0.0224 (11) | 0.0088 (9) |
O9 | 0.0560 (15) | 0.0799 (16) | 0.0739 (15) | 0.0319 (13) | 0.0401 (13) | 0.0426 (14) |
O10 | 0.0516 (13) | 0.0525 (12) | 0.0569 (12) | 0.0177 (11) | 0.0255 (10) | 0.0174 (9) |
O11 | 0.0517 (15) | 0.0652 (14) | 0.0678 (16) | 0.0129 (12) | 0.0255 (12) | 0.0150 (12) |
O12 | 0.0553 (15) | 0.0553 (13) | 0.0693 (14) | 0.0285 (12) | 0.0101 (12) | −0.0047 (11) |
Geometric parameters (Å, º) top
C1—C11 | 1.534 (3) | C16—H17B | 0.96 |
C1—C14 | 1.551 (3) | C16—H17C | 0.96 |
C1—C15 | 1.567 (4) | C17—H16A | 0.96 |
C1—C2 | 1.569 (3) | C17—H16B | 0.96 |
C2—O2 | 1.453 (3) | C17—H16C | 0.96 |
C2—C3 | 1.547 (3) | C18—O9 | 1.192 (4) |
C2—H2 | 0.98 | C18—O2 | 1.347 (4) |
C3—C4 | 1.546 (3) | C18—C19 | 1.499 (5) |
C3—C8 | 1.574 (3) | C19—H21A | 0.96 |
C3—H3 | 0.98 | C19—H21B | 0.96 |
C4—O3 | 1.453 (3) | C19—H21C | 0.96 |
C4—C22 | 1.524 (4) | C20—O10 | 1.207 (4) |
C4—C5 | 1.544 (4) | C20—O3 | 1.351 (4) |
C5—O4 | 1.464 (3) | C20—C21 | 1.489 (4) |
C5—C6 | 1.517 (4) | C21—H25A | 0.96 |
C5—H5 | 0.98 | C21—H25B | 0.96 |
C6—C7 | 1.531 (4) | C21—H25C | 0.96 |
C6—H6A | 0.97 | C22—O4 | 1.449 (4) |
C6—H6B | 0.97 | C22—H20A | 0.97 |
C7—O5 | 1.452 (3) | C22—H20B | 0.97 |
C7—C8 | 1.539 (4) | C23—O11 | 1.207 (4) |
C7—H7A | 0.98 | C23—O5 | 1.333 (4) |
C8—C25 | 1.544 (3) | C23—C24 | 1.496 (5) |
C8—C9 | 1.556 (3) | C24—H27A | 0.96 |
C9—O6 | 1.448 (3) | C24—H27B | 0.96 |
C9—C10 | 1.527 (3) | C24—H27C | 0.96 |
C9—H9 | 0.98 | C25—H19A | 0.96 |
C10—O7 | 1.424 (3) | C25—H19B | 0.96 |
C10—C11 | 1.513 (3) | C25—H19C | 0.96 |
C10—H10 | 0.98 | C26—O12 | 1.188 (4) |
C11—C12 | 1.335 (4) | C26—O6 | 1.338 (3) |
C12—C13 | 1.500 (4) | C26—C27 | 1.500 (4) |
C12—C28 | 1.505 (4) | C27—H29A | 0.96 |
C13—O8 | 1.422 (4) | C27—H29B | 0.96 |
C13—C14 | 1.514 (4) | C27—H29C | 0.96 |
C13—H13 | 0.98 | C28—H18A | 0.96 |
C14—H14A | 0.97 | C28—H18B | 0.96 |
C14—H14B | 0.97 | C28—H18C | 0.96 |
C15—O1 | 1.447 (3) | O1—H1 | 0.82 |
C15—C16 | 1.530 (4) | O7—H7 | 0.82 |
C15—C17 | 1.532 (4) | O8—H8 | 0.82 |
C16—H17A | 0.96 | | |
| | | |
C11—C1—C14 | 100.8 (2) | O1—C15—C17 | 108.7 (2) |
C11—C1—C15 | 111.87 (19) | C16—C15—C17 | 108.7 (2) |
C14—C1—C15 | 111.4 (2) | O1—C15—C1 | 105.6 (2) |
C11—C1—C2 | 110.70 (19) | C16—C15—C1 | 112.2 (2) |
C14—C1—C2 | 110.34 (19) | C17—C15—C1 | 113.7 (2) |
C15—C1—C2 | 111.3 (2) | C15—C16—H17A | 109.5 |
O2—C2—C3 | 110.7 (2) | C15—C16—H17B | 109.5 |
O2—C2—C1 | 107.27 (18) | H17A—C16—H17B | 109.5 |
C3—C2—C1 | 110.50 (19) | C15—C16—H17C | 109.5 |
O2—C2—H2 | 109.4 | H17A—C16—H17C | 109.5 |
C3—C2—H2 | 109.4 | H17B—C16—H17C | 109.5 |
C1—C2—H2 | 109.4 | C15—C17—H16A | 109.5 |
C4—C3—C2 | 116.3 (2) | C15—C17—H16B | 109.5 |
C4—C3—C8 | 113.58 (19) | H16A—C17—H16B | 109.5 |
C2—C3—C8 | 112.0 (2) | C15—C17—H16C | 109.5 |
C4—C3—H3 | 104.5 | H16A—C17—H16C | 109.5 |
C2—C3—H3 | 104.5 | H16B—C17—H16C | 109.5 |
C8—C3—H3 | 104.5 | O9—C18—O2 | 124.6 (3) |
O3—C4—C22 | 109.5 (2) | O9—C18—C19 | 125.5 (3) |
O3—C4—C5 | 113.4 (2) | O2—C18—C19 | 109.9 (3) |
C22—C4—C5 | 85.5 (2) | C18—C19—H21A | 109.5 |
O3—C4—C3 | 108.81 (19) | C18—C19—H21B | 109.5 |
C22—C4—C3 | 120.8 (2) | H21A—C19—H21B | 109.5 |
C5—C4—C3 | 117.2 (2) | C18—C19—H21C | 109.5 |
O4—C5—C6 | 112.3 (2) | H21A—C19—H21C | 109.5 |
O4—C5—C4 | 89.9 (2) | H21B—C19—H21C | 109.5 |
C6—C5—C4 | 119.5 (2) | O10—C20—O3 | 122.8 (2) |
O4—C5—H5 | 111.1 | O10—C20—C21 | 125.3 (3) |
C6—C5—H5 | 111.1 | O3—C20—C21 | 111.9 (3) |
C4—C5—H5 | 111.1 | C20—C21—H25A | 109.5 |
C5—C6—C7 | 115.9 (2) | C20—C21—H25B | 109.5 |
C5—C6—H6A | 108.3 | H25A—C21—H25B | 109.5 |
C7—C6—H6A | 108.3 | C20—C21—H25C | 109.5 |
C5—C6—H6B | 108.3 | H25A—C21—H25C | 109.5 |
C7—C6—H6B | 108.3 | H25B—C21—H25C | 109.5 |
H6A—C6—H6B | 107.4 | O4—C22—C4 | 91.3 (2) |
O5—C7—C6 | 104.0 (2) | O4—C22—H20A | 113.4 |
O5—C7—C8 | 112.9 (2) | C4—C22—H20A | 113.4 |
C6—C7—C8 | 114.0 (2) | O4—C22—H20B | 113.4 |
O5—C7—H7A | 108.6 | C4—C22—H20B | 113.4 |
C6—C7—H7A | 108.6 | H20A—C22—H20B | 110.7 |
C8—C7—H7A | 108.6 | O11—C23—O5 | 124.3 (3) |
C7—C8—C25 | 111.4 (2) | O11—C23—C24 | 123.9 (3) |
C7—C8—C9 | 114.7 (2) | O5—C23—C24 | 111.7 (3) |
C25—C8—C9 | 105.5 (2) | C23—C24—H27A | 109.5 |
C7—C8—C3 | 103.80 (19) | C23—C24—H27B | 109.5 |
C25—C8—C3 | 113.9 (2) | H27A—C24—H27B | 109.5 |
C9—C8—C3 | 107.85 (18) | C23—C24—H27C | 109.5 |
O6—C9—C10 | 105.07 (19) | H27A—C24—H27C | 109.5 |
O6—C9—C8 | 108.81 (19) | H27B—C24—H27C | 109.5 |
C10—C9—C8 | 120.46 (19) | C8—C25—H19A | 109.5 |
O6—C9—H9 | 107.3 | C8—C25—H19B | 109.5 |
C10—C9—H9 | 107.3 | H19A—C25—H19B | 109.5 |
C8—C9—H9 | 107.3 | C8—C25—H19C | 109.5 |
O7—C10—C11 | 111.6 (2) | H19A—C25—H19C | 109.5 |
O7—C10—C9 | 108.61 (19) | H19B—C25—H19C | 109.5 |
C11—C10—C9 | 114.52 (19) | O12—C26—O6 | 124.8 (3) |
O7—C10—H10 | 107.2 | O12—C26—C27 | 124.8 (3) |
C11—C10—H10 | 107.2 | O6—C26—C27 | 110.4 (3) |
C9—C10—H10 | 107.2 | C26—C27—H29A | 109.5 |
C12—C11—C10 | 122.6 (2) | C26—C27—H29B | 109.5 |
C12—C11—C1 | 112.2 (2) | H29A—C27—H29B | 109.5 |
C10—C11—C1 | 125.2 (2) | C26—C27—H29C | 109.5 |
C11—C12—C13 | 112.1 (2) | H29A—C27—H29C | 109.5 |
C11—C12—C28 | 127.4 (3) | H29B—C27—H29C | 109.5 |
C13—C12—C28 | 120.6 (2) | C12—C28—H18A | 109.5 |
O8—C13—C12 | 111.8 (3) | C12—C28—H18B | 109.5 |
O8—C13—C14 | 109.1 (2) | H18A—C28—H18B | 109.5 |
C12—C13—C14 | 103.4 (2) | C12—C28—H18C | 109.5 |
O8—C13—H13 | 110.8 | H18A—C28—H18C | 109.5 |
C12—C13—H13 | 110.8 | H18B—C28—H18C | 109.5 |
C14—C13—H13 | 110.8 | C15—O1—H1 | 109.5 |
C13—C14—C1 | 108.1 (2) | C18—O2—C2 | 119.2 (2) |
C13—C14—H14A | 110.1 | C20—O3—C4 | 117.0 (2) |
C1—C14—H14A | 110.1 | C22—O4—C5 | 91.30 (19) |
C13—C14—H14B | 110.1 | C23—O5—C7 | 118.7 (2) |
C1—C14—H14B | 110.1 | C26—O6—C9 | 118.1 (2) |
H14A—C14—H14B | 108.4 | C10—O7—H7 | 109.5 |
O1—C15—C16 | 107.6 (2) | C13—O8—H8 | 109.5 |
| | | |
C11—C1—C2—O2 | 148.57 (19) | C14—C1—C11—C12 | −11.9 (3) |
C14—C1—C2—O2 | 37.9 (3) | C15—C1—C11—C12 | 106.5 (2) |
C15—C1—C2—O2 | −86.3 (2) | C2—C1—C11—C12 | −128.7 (2) |
C11—C1—C2—C3 | 27.8 (3) | C14—C1—C11—C10 | 168.6 (2) |
C14—C1—C2—C3 | −82.9 (3) | C15—C1—C11—C10 | −73.0 (3) |
C15—C1—C2—C3 | 152.90 (19) | C2—C1—C11—C10 | 51.8 (3) |
O2—C2—C3—C4 | 11.9 (3) | C10—C11—C12—C13 | −179.3 (2) |
C1—C2—C3—C4 | 130.6 (2) | C1—C11—C12—C13 | 1.2 (3) |
O2—C2—C3—C8 | 144.85 (19) | C10—C11—C12—C28 | 0.7 (4) |
C1—C2—C3—C8 | −96.5 (2) | C1—C11—C12—C28 | −178.8 (3) |
C2—C3—C4—O3 | −69.9 (3) | C11—C12—C13—O8 | 127.6 (2) |
C8—C3—C4—O3 | 157.9 (2) | C28—C12—C13—O8 | −52.4 (3) |
C2—C3—C4—C22 | 58.0 (3) | C11—C12—C13—C14 | 10.4 (3) |
C8—C3—C4—C22 | −74.2 (3) | C28—C12—C13—C14 | −169.6 (3) |
C2—C3—C4—C5 | 159.8 (2) | O8—C13—C14—C1 | −136.8 (2) |
C8—C3—C4—C5 | 27.5 (3) | C12—C13—C14—C1 | −17.7 (3) |
O3—C4—C5—O4 | 119.6 (2) | C11—C1—C14—C13 | 17.9 (3) |
C22—C4—C5—O4 | 10.3 (2) | C15—C1—C14—C13 | −100.9 (3) |
C3—C4—C5—O4 | −112.2 (2) | C2—C1—C14—C13 | 135.0 (2) |
O3—C4—C5—C6 | −124.6 (3) | C11—C1—C15—O1 | 56.1 (2) |
C22—C4—C5—C6 | 126.1 (3) | C14—C1—C15—O1 | 168.1 (2) |
C3—C4—C5—C6 | 3.6 (4) | C2—C1—C15—O1 | −68.3 (2) |
O4—C5—C6—C7 | 104.3 (3) | C11—C1—C15—C16 | −60.9 (3) |
C4—C5—C6—C7 | 1.0 (4) | C14—C1—C15—C16 | 51.1 (3) |
C5—C6—C7—O5 | −161.4 (2) | C2—C1—C15—C16 | 174.7 (2) |
C5—C6—C7—C8 | −38.1 (3) | C11—C1—C15—C17 | 175.3 (2) |
O5—C7—C8—C25 | 61.6 (3) | C14—C1—C15—C17 | −72.8 (3) |
C6—C7—C8—C25 | −56.7 (3) | C2—C1—C15—C17 | 50.8 (3) |
O5—C7—C8—C9 | −58.1 (3) | O3—C4—C22—O4 | −123.7 (2) |
C6—C7—C8—C9 | −176.44 (19) | C5—C4—C22—O4 | −10.4 (2) |
O5—C7—C8—C3 | −175.52 (18) | C3—C4—C22—O4 | 108.8 (3) |
C6—C7—C8—C3 | 66.2 (2) | O9—C18—O2—C2 | 1.5 (4) |
C4—C3—C8—C7 | −60.0 (3) | C19—C18—O2—C2 | −177.9 (3) |
C2—C3—C8—C7 | 165.76 (19) | C3—C2—O2—C18 | −106.6 (3) |
C4—C3—C8—C25 | 61.2 (3) | C1—C2—O2—C18 | 132.7 (2) |
C2—C3—C8—C25 | −73.0 (3) | O10—C20—O3—C4 | 2.1 (4) |
C4—C3—C8—C9 | 177.9 (2) | C21—C20—O3—C4 | −178.0 (2) |
C2—C3—C8—C9 | 43.7 (2) | C22—C4—O3—C20 | 147.4 (2) |
C7—C8—C9—O6 | 55.0 (3) | C5—C4—O3—C20 | 53.8 (3) |
C25—C8—C9—O6 | −67.9 (2) | C3—C4—O3—C20 | −78.6 (3) |
C3—C8—C9—O6 | 170.11 (19) | C4—C22—O4—C5 | 11.0 (2) |
C7—C8—C9—C10 | −66.2 (3) | C6—C5—O4—C22 | −132.9 (3) |
C25—C8—C9—C10 | 170.9 (2) | C4—C5—O4—C22 | −10.8 (2) |
C3—C8—C9—C10 | 48.8 (3) | O11—C23—O5—C7 | −4.8 (4) |
O6—C9—C10—O7 | 58.3 (2) | C24—C23—O5—C7 | 176.8 (3) |
C8—C9—C10—O7 | −178.7 (2) | C6—C7—O5—C23 | −119.3 (3) |
O6—C9—C10—C11 | −176.2 (2) | C8—C7—O5—C23 | 116.7 (3) |
C8—C9—C10—C11 | −53.1 (3) | O12—C26—O6—C9 | −5.5 (4) |
O7—C10—C11—C12 | −89.4 (3) | C27—C26—O6—C9 | 175.7 (3) |
C9—C10—C11—C12 | 146.7 (2) | C10—C9—O6—C26 | −110.8 (2) |
O7—C10—C11—C1 | 90.1 (3) | C8—C9—O6—C26 | 118.9 (2) |
C9—C10—C11—C1 | −33.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7···O1 | 0.82 | 2.02 | 2.740 (3) | 146 |
O1—H1···O11i | 0.82 | 2.08 | 2.883 (3) | 168 |
O8—H8···O4ii | 0.82 | 2.08 | 2.845 (3) | 154 |
O8—H8···O12iii | 0.82 | 2.64 | 3.075 (3) | 115 |
C6—H6B···O9iv | 0.97 | 2.42 | 3.366 (5) | 166 |
C9—H9···O1 | 0.98 | 2.44 | 3.136 (3) | 128 |
C25—H19C···O4 | 0.96 | 2.28 | 3.123 (4) | 146 |
C22—H20B···O9 | 0.97 | 2.42 | 3.258 (5) | 144 |
C24—H27C···O12iv | 0.96 | 2.48 | 3.443 (6) | 175 |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x, y+1, z+1; (iv) x−1, y, z. |