research communications
Withanolides from Physalis angulata L.
aS.Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences, of Uzbekistan 100170, Mirzo Ulugbek Str., 77, Tashkent, Uzbekistan, and bTashkent Chemical-Technological Institute, of Uzbekistan 100011, A. Navoiy Str., 32, Tashkent, Uzbekistan
*Correspondence e-mail: raxul@mail.ru
The compounds (17S,20R,22R,24R,25S)-5β,6β:20,24-diepoxy-4β,25-dihydroxy-1-oxowith-2-en-26,22-olide and (20R,22R)-5α,14α,20-Trihydroxy-1-oxo-6α,7α-epoxywitha-2-enolide were isolated from a chloroform extract of the aerial parts of Physalis angulata L. (Solanaceae). Two products were isolated from the chromatographic separation extract. Compound I corresponds to physangulide B chloroform monosolvate, C28H38O7·CHCl3, while compound II is 14α-hydroxyixocarpanolide, C28H40O7. In the two molecular structures, the conformation of the steroid part (rings A, B, C, D) does not differ. In both crystals, molecules are linked by intermolecular O—H⋯O hydrogen bonds along the c-axis direction and form a two-dimensional network parallel to the ac plane. The was determined from X-ray diffraction data.
1. Chemical context
The genus Physalis belongs to the nightshade family of plants and is widely distributed in subtropical and tropical regions around the world. Some Physalis species are important in the diet because of their edible fruits. Phytochemical and pharmacological studies show that in plants of the genus Physalis, the main biological substances are withanolides (Huang et al., 2020). The fruits of Physalis angulata L. are edible, traditionally collected from wild populations, but the plant is now widely cultivated. In different countries of the world the fruits, roots and leaves of Physalis angulata L. are used in folk medicine as a treatment for various diseases (Salgado & Arana, 2013). The main of Physalis angulata are withanolides, which are highly variable in chemical structure and exhibit interesting pharmacological activity (Ray & Gupta, 1994; Figueiredo et al., 2020; Sá et al., 2011; Pinto et al., 2016). The plant Physalis angulata is widespread in Uzbekistan and its reserves are sufficient for industrial use (Vasina et al., 1990).
To study the chemical structure of withanolides, leaves of Physalis angulata collected in the Tashkent region were used. Isolation of withanolides from the leaves of Physalis angulata and separation of components into individual substances was carried out by The isolated compounds were identified as physangulide B chloroform solvate (I) and 14α-hydroxyixocarpanolide (II).
2. Structural commentary
The I, a chloroform solvate of physangulide B, is shown in Fig. 1. The use of Cu Kα radiation allowed the determination of the of the physangulide B molecule. The refined to 0.014 (6). The chiral centres of the physangulide B molecule have the following 4S, 5R, 6R, 8S, 9S,10R, 13S, 14S, 17S, 20R, 22R, 24R and 25S. The stereochemistry of physangulide B [systematic name (17S,20R,22R,24R,25S)-5β,6β:20,24-diepoxy-4β,25-dihydroxy-1-oxowith-2-en-26,22-olide] does not differ from that found for the acetyl derivative and confirms the proposed earlier for physangulide B (Maldonado et al., 2015).
ofThe molecular structure of withanolide II is shown in Fig. 2. The refined to −0.1 (2) and allowed the of II to be confirmed. The chiral centres in the molecule have the following 5R, 6S, 7S, 8S, 9S, 10R, 13R, 14R, 17S, 20R, 22R, 24S, 25R. According to the experimental data, the isolated compound is 14α-hydroxyixocarpanolide [systematic name: (20R,22R)-5α,14α,20-trihydroxy-1-oxo-6α,7α-epoxywitha-2-enolide (Vasina et al., 1986; Ray & Gupta, 1994).
In both molecules, ring C adopts a chair conformation and ring D an with atom C13 as the flap. Ring A exhibits a half–chair conformation, but differs slightly in the arrangement of atoms. The C1–C4 fragment is planar with r.m.s deviations of 0.0045 Å for I and 0.034 Å for II. The deviations of atoms C5 and C10 atoms from this plane are −0.225 (7) and 0.291 (7) Å, respectively, for I and −0.478 (7) and 0.280 (7) Å for II.
In the molecule of I, atoms of ring B are located in one plane (with an r.m.s deviation of 0.0132 Å), except for C8 which deviates from the plane of the remaining atoms by 0.666 (4) Å. A similar for ring B is observed in II. Here, the C5–C9 atoms are located in one plane with an accuracy of 0.0643 Å, atom C10 being displaced from the plane through the remaining atoms by 0.696 (4) Å. This difference in the arrangement of atoms in planes is explained by the position of the epoxy bridge, which is located in the β-position for I and the α-position for II.
3. Supramolecular features
In both crystal structures, intermolecular hydrogen bonds of the O—H⋯O type are observed, which link the molecules along the c-axis direction. In compound I, O—H⋯O and C—H⋯O hydrogen bonds are observed between molecules of physangulide B (Table 1). O4—H4⋯O26 and O25—H25⋯O56 hydrogen bonds are involved in the formation of an infinite chain along the c-axis (Fig. 3). In addition, the chloroform molecule participates in a hydrogen bond with the oxygen atom O26 of the lactone fragment. A similar hydrogen bond with a solvate molecule (methanol) is observed in the structure of the acetyl derivative of physangulide B (FUQKAF; Maldonado et al., 2015).
Similar intermolecular O—H⋯O and C—H⋯O hydrogen bonds are observed in the structure of II (Table 2). The formation of an infinite O20—H20⋯O5 hydrogen-bonded chain is shown in Fig. 4. Paired hydrogen bonds are observed between molecules, which extend along the c-axis direction.
4. Database survey
A search for related structures (A, B, C, D, E rings are connected according to the order of the studied compounds) in the Cambridge Structural Database (CSD Version 5.42, update of November 2020; Groom et al., 2016) resulted in eleven hits. Of the structures found, the closest structure considering the connectivity and of atoms is 17-(4-hydroxy-4,5,7-trimethyl-3-oxo-2,6-dioxabicyclo[3.2.1]oct-7-yl)-1-oxo-5,6-epoxyandrost-2-en-4-yl acetate methanol solvate (FUQKAF; Maldonado et al., 2015). Structures with the 5β,6β-epoxy-4β-hydroxy groups in the same location in the molecule as the title compounds are 4,16,20,24-tetrahydroxy-5,6:22,26-diepoxyergost-2-ene-1,26-dione methanol solvate (GANFOS, Maldonado et al., 2011), (17R,20R,22R,24S,25R)-4β,17α,20β-trihydroxy-5β,6β-epoxy-1-oxowitha-2-en-26,22-olide (Philadelphicalactone A, XIVYEG; Su et al., 2002) and (17R,20S,22R)-4β-hydroxy-1-oxo-5β,6β-epoxy-16α-acetoxywitha-2-enolide ethyl acetate clathrate (YISSOI; Alfonso et al., 1993).
5. Synthesis and crystallization
Isolation of individual substances from the leaves of Physalis angulata
Collected dried leaves (4 kg) of Physalis angulata L. were poured into cold water and heated to boiling. The hot mass was squeezed out through a canvas. The plant was again poured into cold water, heated, and the hot mass was squeezed out through the canvas again. The water extract was distilled until the volume decreased to 3 L. Chloroform (3 L) was poured into the received solution and substances were extracted. From the chloroform layer, insoluble and soluble substances (25 g) were isolated. To the isolated dry mass, 0.5 L of chloroform were added and the solution was filtered (the mass of the insoluble compounds was 5.8 g). From the filtrate after distillation, 19.2 g of compounds were isolated. The compounds isolated from the filtrate were loaded onto a column containing 0.5 kg of silica gel (Silica gel 60, 0.063-0.1 mm, Merck). The sums of substances were eluted with system 1 (chloroform:methanol 99:1) to produce fractions 1–5, and eluted with system 2 (chloroform:methanol 97:3) to produce fractions 5–9. The process was monitored by thin layer (Silica gel on TLC Al foils, fluorescent indicator 254 nm). Fractions 2–4 (6.8 g) and 6–8 (4.0 g) were shown by TLC to consist of individual substances.
The obtained fractions were purified by repeated RF in system 3 was 0.58, visualized as a crimson spot. The yield was 0.15%, based on the weight of the air-dry raw material. Rechromatography of fractions 6–8 in system 1 yielded 3.6 g of 14α-hydroxyixocarpanolide, RF = 0.34 in system 2, visualized as a pink spot. The yield was 0.028%.
Rechromatography of fractions 2–4 containing physangulide B in system 3 (chloroform:methanol 10:1) gave 5.96 g of the individual product. ThePhysangulide B [(17S,20R,22R,24R,25S)-5β,6β:20,24-diepoxy-4β,25-dihydroxy-1-oxowith-2-en-26,22-olide]
C28H40O7 (methanol), m.p. 553–555 K, [α]20D = −56.0 (c = 0.21, CHCl3). UV spectrum, λCH3OHmax (logɛ 5600) 212 (4.00) nm. IR (FT–IR, νKBrmax, cm−1): 3411 (v br, O—H str), 2958 (m, Csycl—H str), 1706 (s, C=O str), 1676 (v s, C=O), 1457 (m), 1380 (m), 1272 (s), 1101 (s), 1085 (m), 1024 (m), 962 (m), 921 (w), 905 (w).
14α-hydroxyixocarpanolide (5α,14α,20R-trihydroxy-1-oxo-6α,7α-epoxywitha-2-enolide)
C28H40O7 (methanol), mp. 528–530 K, [α]20D = + 29.1 ±2 (c = 1.18, CHCl3). UV spectrum, λC2H5OHmax: 225 nm (ɛ 10370). IR (FT–IR, νKBrmax, cm−1): 3584–3477 (v br, O—H str), 2949 (m, Csycl—H str), 1754 (v s, C=O str), 1458 (w), 1388 (m), 1261 (s), 1182 (m), 1094 (v), 1034 (m), 910 (m).
6. Refinement
Crystal data, data collection and structure . The H atoms bonded to C atoms were placed geometrically (with C—H distances of 0.98 Å for CH, 0.97 Å for CH2, 0.96 Å for CH3 and 0.93 Å for Car) and included in the in a riding-motion approximation with Uiso(H) = 1.2Ueq(C) [Uiso = 1.5Ueq(C) for methyl H atoms]. The hydrogen atoms on the O atoms were located in difference-Fourier maps and refined freely.
details are summarized in Table 3
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Supporting information
https://doi.org/10.1107/S205698902100709X/dj2029sup1.cif
contains datablocks I, II, Global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902100709X/dj2029Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S205698902100709X/dj2029IIsup3.hkl
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2018); cell
CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018). Program(s) used to solve structure: SHELXS7 (Sheldrick, 2008) for (II). For both structures, program(s) used to refine structure: SHELXL2014/8 (Sheldrick, 2015); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2020) and publCIF (Westrip, 2010)'.C28H38O7·CHCl3 | Dx = 1.357 Mg m−3 |
Mr = 605.95 | Melting point: 553(2) K |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 7.3633 (15) Å | Cell parameters from 7825 reflections |
b = 15.952 (3) Å | θ = 5.5–76.0° |
c = 12.657 (3) Å | µ = 3.17 mm−1 |
β = 94.14 (3)° | T = 290 K |
V = 1482.9 (5) Å3 | Prizmatic, colorless |
Z = 2 | 0.50 × 0.34 × 0.31 mm |
F(000) = 640 |
Rigaku Xcalibur, Ruby diffractometer | 5743 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 5622 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.2576 pixels mm-1 | θmax = 75.9°, θmin = 3.5° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −19→19 |
Tmin = 0.316, Tmax = 0.376 | l = −13→15 |
13820 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0643P)2 + 0.4392P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.113 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.41 e Å−3 |
5743 reflections | Δρmin = −0.34 e Å−3 |
365 parameters | Absolute structure: Flack x determined using 2401 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.014 (6) |
Primary atom site location: structure-invariant direct methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.5252 (5) | 0.9171 (2) | 0.5852 (2) | 0.0678 (9) | |
O2 | 1.0029 (3) | 0.76628 (14) | 0.21727 (16) | 0.0380 (5) | |
O3 | 1.1887 (3) | 0.60670 (14) | 0.22825 (16) | 0.0357 (4) | |
O4 | 0.5431 (5) | 0.8210 (2) | 0.9630 (2) | 0.0619 (8) | |
O25 | 1.0440 (4) | 0.6971 (2) | −0.02618 (18) | 0.0534 (7) | |
O26 | 0.7584 (3) | 0.7338 (2) | 0.1201 (2) | 0.0598 (7) | |
O56 | 0.7082 (3) | 0.70353 (16) | 0.84614 (16) | 0.0419 (5) | |
C1 | 0.5220 (5) | 0.8852 (2) | 0.6718 (3) | 0.0402 (7) | |
C2 | 0.3764 (5) | 0.9089 (3) | 0.7396 (3) | 0.0530 (9) | |
H2A | 0.3045 | 0.9551 | 0.7202 | 0.064* | |
C3 | 0.3425 (5) | 0.8679 (3) | 0.8265 (3) | 0.0513 (9) | |
H3A | 0.2463 | 0.8858 | 0.8646 | 0.062* | |
C4 | 0.4509 (5) | 0.7944 (2) | 0.8665 (3) | 0.0442 (7) | |
H4B | 0.3664 | 0.7494 | 0.8824 | 0.053* | |
C5 | 0.5835 (4) | 0.7603 (2) | 0.7888 (2) | 0.0322 (6) | |
C6 | 0.5780 (4) | 0.6705 (2) | 0.7655 (2) | 0.0352 (6) | |
H6A | 0.4750 | 0.6394 | 0.7912 | 0.042* | |
C7 | 0.6634 (4) | 0.63329 (18) | 0.6726 (2) | 0.0330 (6) | |
H7A | 0.5713 | 0.6264 | 0.6145 | 0.040* | |
H7B | 0.7116 | 0.5783 | 0.6915 | 0.040* | |
C8 | 0.8166 (4) | 0.68855 (17) | 0.63666 (19) | 0.0271 (5) | |
H8A | 0.9182 | 0.6886 | 0.6911 | 0.032* | |
C9 | 0.7496 (4) | 0.77894 (17) | 0.6166 (2) | 0.0277 (5) | |
H9A | 0.6484 | 0.7747 | 0.5622 | 0.033* | |
C10 | 0.6687 (4) | 0.82253 (18) | 0.7140 (2) | 0.0298 (5) | |
C11 | 0.8951 (5) | 0.83293 (19) | 0.5672 (3) | 0.0394 (7) | |
H11A | 0.8440 | 0.8877 | 0.5499 | 0.047* | |
H11B | 0.9972 | 0.8408 | 0.6191 | 0.047* | |
C12 | 0.9643 (5) | 0.79385 (19) | 0.4669 (3) | 0.0385 (7) | |
H12A | 0.8658 | 0.7922 | 0.4117 | 0.046* | |
H12B | 1.0607 | 0.8285 | 0.4420 | 0.046* | |
C13 | 1.0362 (3) | 0.70547 (18) | 0.4875 (2) | 0.0283 (5) | |
C14 | 0.8816 (4) | 0.65438 (16) | 0.53265 (19) | 0.0269 (5) | |
H14A | 0.7772 | 0.6588 | 0.4804 | 0.032* | |
C15 | 0.9460 (5) | 0.5629 (2) | 0.5285 (3) | 0.0420 (7) | |
H15A | 0.8432 | 0.5248 | 0.5209 | 0.050* | |
H15B | 1.0208 | 0.5483 | 0.5921 | 0.050* | |
C16 | 1.0582 (5) | 0.5598 (2) | 0.4299 (3) | 0.0401 (7) | |
H16A | 1.0015 | 0.5225 | 0.3767 | 0.048* | |
H16B | 1.1809 | 0.5402 | 0.4490 | 0.048* | |
C17 | 1.0614 (4) | 0.65077 (18) | 0.3875 (2) | 0.0292 (5) | |
H17A | 0.9476 | 0.6571 | 0.3431 | 0.035* | |
C18 | 1.2062 (4) | 0.7062 (3) | 0.5657 (3) | 0.0479 (8) | |
H18A | 1.1720 | 0.7221 | 0.6347 | 0.072* | |
H18B | 1.2929 | 0.7458 | 0.5422 | 0.072* | |
H18C | 1.2596 | 0.6513 | 0.5691 | 0.072* | |
C19 | 0.8116 (5) | 0.8745 (2) | 0.7823 (3) | 0.0434 (7) | |
H19A | 0.7590 | 0.8937 | 0.8451 | 0.065* | |
H19B | 0.8486 | 0.9219 | 0.7423 | 0.065* | |
H19C | 0.9157 | 0.8401 | 0.8016 | 0.065* | |
C20 | 1.2141 (4) | 0.6683 (2) | 0.3131 (2) | 0.0332 (6) | |
C21 | 1.4095 (4) | 0.6596 (3) | 0.3637 (3) | 0.0509 (9) | |
H21A | 1.4926 | 0.6545 | 0.3090 | 0.076* | |
H21B | 1.4176 | 0.6105 | 0.4078 | 0.076* | |
H21C | 1.4401 | 0.7082 | 0.4059 | 0.076* | |
C22 | 1.1939 (4) | 0.7507 (2) | 0.2501 (2) | 0.0371 (6) | |
H22A | 1.2487 | 0.7980 | 0.2902 | 0.045* | |
C23 | 1.2941 (4) | 0.7319 (2) | 0.1529 (3) | 0.0406 (7) | |
H23A | 1.4249 | 0.7303 | 0.1687 | 0.049* | |
H23B | 1.2645 | 0.7717 | 0.0964 | 0.049* | |
C24 | 1.2164 (4) | 0.6451 (2) | 0.1265 (2) | 0.0336 (6) | |
C25 | 1.0239 (4) | 0.6579 (2) | 0.0736 (2) | 0.0378 (6) | |
C26 | 0.9179 (4) | 0.7211 (2) | 0.1396 (2) | 0.0389 (7) | |
C27 | 0.9140 (6) | 0.5779 (3) | 0.0607 (3) | 0.0568 (9) | |
H27A | 0.9777 | 0.5384 | 0.0197 | 0.085* | |
H27B | 0.7975 | 0.5900 | 0.0251 | 0.085* | |
H27C | 0.8972 | 0.5545 | 0.1292 | 0.085* | |
C28 | 1.3367 (5) | 0.5895 (3) | 0.0646 (3) | 0.0470 (8) | |
H28A | 1.4541 | 0.5844 | 0.1021 | 0.070* | |
H28B | 1.3501 | 0.6138 | −0.0038 | 0.070* | |
H28C | 1.2822 | 0.5351 | 0.0560 | 0.070* | |
C1S | 0.6099 (7) | 0.9209 (3) | 0.2081 (4) | 0.0664 (11) | |
H1SA | 0.6333 | 0.8640 | 0.1832 | 0.080* | |
Cl1 | 0.4179 (2) | 0.96088 (8) | 0.13542 (10) | 0.0782 (4) | |
Cl2 | 0.5718 (2) | 0.91662 (10) | 0.34355 (10) | 0.0863 (4) | |
Cl3 | 0.8008 (3) | 0.98341 (14) | 0.18974 (14) | 0.1059 (5) | |
H4 | 0.605 (7) | 0.785 (4) | 0.989 (4) | 0.063 (15)* | |
H25 | 0.958 (7) | 0.692 (3) | −0.060 (4) | 0.051 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.085 (2) | 0.0663 (18) | 0.0546 (15) | 0.0371 (16) | 0.0221 (14) | 0.0254 (14) |
O2 | 0.0421 (11) | 0.0384 (11) | 0.0345 (10) | 0.0095 (9) | 0.0089 (8) | 0.0018 (9) |
O3 | 0.0427 (11) | 0.0366 (11) | 0.0287 (9) | 0.0043 (9) | 0.0091 (8) | −0.0020 (8) |
O4 | 0.080 (2) | 0.075 (2) | 0.0318 (12) | 0.0277 (17) | 0.0112 (12) | −0.0065 (12) |
O25 | 0.0432 (13) | 0.088 (2) | 0.0295 (11) | 0.0046 (13) | 0.0045 (10) | 0.0098 (12) |
O26 | 0.0373 (12) | 0.091 (2) | 0.0506 (14) | 0.0193 (13) | 0.0029 (10) | −0.0003 (14) |
O56 | 0.0490 (12) | 0.0505 (13) | 0.0262 (9) | 0.0114 (10) | 0.0030 (8) | 0.0049 (9) |
C1 | 0.0474 (17) | 0.0348 (15) | 0.0387 (15) | 0.0085 (13) | 0.0053 (13) | 0.0011 (12) |
C2 | 0.0483 (19) | 0.059 (2) | 0.053 (2) | 0.0247 (17) | 0.0064 (15) | 0.0003 (17) |
C3 | 0.0397 (17) | 0.069 (2) | 0.0473 (18) | 0.0138 (17) | 0.0137 (14) | −0.0081 (16) |
C4 | 0.0468 (17) | 0.0505 (19) | 0.0378 (16) | 0.0021 (15) | 0.0187 (13) | −0.0022 (13) |
C5 | 0.0333 (13) | 0.0391 (15) | 0.0246 (12) | 0.0024 (12) | 0.0054 (10) | 0.0014 (11) |
C6 | 0.0389 (14) | 0.0351 (14) | 0.0329 (13) | −0.0017 (12) | 0.0103 (11) | 0.0062 (11) |
C7 | 0.0392 (15) | 0.0277 (13) | 0.0328 (13) | −0.0013 (11) | 0.0073 (11) | 0.0025 (10) |
C8 | 0.0294 (12) | 0.0292 (13) | 0.0227 (11) | 0.0003 (10) | 0.0024 (9) | 0.0000 (9) |
C9 | 0.0314 (13) | 0.0270 (13) | 0.0250 (12) | −0.0003 (10) | 0.0047 (9) | −0.0021 (9) |
C10 | 0.0322 (13) | 0.0309 (13) | 0.0273 (12) | 0.0023 (11) | 0.0081 (10) | −0.0029 (10) |
C11 | 0.0497 (18) | 0.0273 (14) | 0.0438 (16) | −0.0060 (13) | 0.0213 (13) | −0.0064 (12) |
C12 | 0.0487 (17) | 0.0290 (14) | 0.0405 (16) | −0.0010 (12) | 0.0211 (13) | 0.0006 (11) |
C13 | 0.0265 (12) | 0.0343 (14) | 0.0244 (11) | 0.0002 (10) | 0.0040 (9) | −0.0038 (10) |
C14 | 0.0303 (12) | 0.0259 (13) | 0.0246 (11) | 0.0012 (10) | 0.0030 (9) | 0.0002 (9) |
C15 | 0.059 (2) | 0.0291 (15) | 0.0398 (15) | 0.0091 (14) | 0.0154 (14) | 0.0044 (12) |
C16 | 0.0487 (17) | 0.0335 (15) | 0.0393 (15) | 0.0095 (13) | 0.0118 (13) | −0.0007 (12) |
C17 | 0.0288 (12) | 0.0326 (14) | 0.0260 (12) | 0.0038 (10) | 0.0008 (9) | −0.0025 (10) |
C18 | 0.0309 (14) | 0.075 (2) | 0.0369 (15) | −0.0029 (16) | −0.0012 (11) | −0.0169 (16) |
C19 | 0.0470 (17) | 0.0451 (17) | 0.0389 (15) | −0.0091 (14) | 0.0085 (13) | −0.0156 (13) |
C20 | 0.0280 (12) | 0.0431 (16) | 0.0285 (12) | 0.0027 (11) | 0.0028 (10) | −0.0063 (11) |
C21 | 0.0295 (14) | 0.083 (3) | 0.0400 (16) | 0.0072 (16) | 0.0036 (12) | −0.0052 (17) |
C22 | 0.0344 (14) | 0.0407 (16) | 0.0369 (14) | −0.0052 (12) | 0.0073 (11) | −0.0061 (12) |
C23 | 0.0353 (15) | 0.0499 (18) | 0.0379 (15) | −0.0082 (13) | 0.0112 (12) | −0.0015 (13) |
C24 | 0.0305 (13) | 0.0444 (16) | 0.0267 (12) | 0.0014 (12) | 0.0067 (10) | −0.0012 (11) |
C25 | 0.0340 (14) | 0.0517 (18) | 0.0284 (13) | −0.0010 (13) | 0.0072 (10) | 0.0006 (12) |
C26 | 0.0361 (15) | 0.0492 (18) | 0.0322 (14) | 0.0049 (13) | 0.0071 (11) | 0.0087 (12) |
C27 | 0.048 (2) | 0.066 (2) | 0.057 (2) | −0.0129 (18) | 0.0001 (16) | −0.0146 (19) |
C28 | 0.0440 (17) | 0.060 (2) | 0.0383 (16) | 0.0092 (15) | 0.0133 (13) | −0.0056 (14) |
C1S | 0.092 (3) | 0.048 (2) | 0.060 (2) | 0.014 (2) | 0.009 (2) | 0.0038 (19) |
Cl1 | 0.1089 (10) | 0.0598 (6) | 0.0632 (6) | 0.0123 (6) | −0.0128 (6) | −0.0165 (5) |
Cl2 | 0.1101 (10) | 0.0872 (9) | 0.0626 (6) | 0.0276 (8) | 0.0136 (6) | 0.0239 (6) |
Cl3 | 0.1052 (11) | 0.1223 (14) | 0.0904 (10) | −0.0186 (10) | 0.0085 (8) | 0.0238 (9) |
O1—C1 | 1.211 (4) | C13—C17 | 1.559 (4) |
O2—C26 | 1.338 (4) | C14—C15 | 1.536 (4) |
O2—C22 | 1.459 (4) | C14—H14A | 0.9800 |
O3—C24 | 1.454 (3) | C15—C16 | 1.547 (4) |
O3—C20 | 1.458 (3) | C15—H15A | 0.9700 |
O4—C4 | 1.418 (5) | C15—H15B | 0.9700 |
O4—H4 | 0.79 (6) | C16—C17 | 1.547 (4) |
O25—C25 | 1.427 (4) | C16—H16A | 0.9700 |
O25—H25 | 0.74 (5) | C16—H16B | 0.9700 |
O26—C26 | 1.200 (4) | C17—C20 | 1.544 (4) |
O56—C5 | 1.447 (4) | C17—H17A | 0.9800 |
O56—C6 | 1.448 (4) | C18—H18A | 0.9600 |
C1—C2 | 1.470 (5) | C18—H18B | 0.9600 |
C1—C10 | 1.539 (4) | C18—H18C | 0.9600 |
C2—C3 | 1.319 (6) | C19—H19A | 0.9600 |
C2—H2A | 0.9300 | C19—H19B | 0.9600 |
C3—C4 | 1.486 (5) | C19—H19C | 0.9600 |
C3—H3A | 0.9300 | C20—C22 | 1.538 (5) |
C4—C5 | 1.536 (4) | C20—C21 | 1.538 (4) |
C4—H4B | 0.9800 | C21—H21A | 0.9600 |
C5—C6 | 1.463 (4) | C21—H21B | 0.9600 |
C5—C10 | 1.537 (4) | C21—H21C | 0.9600 |
C6—C7 | 1.496 (4) | C22—C23 | 1.511 (4) |
C6—H6A | 0.9800 | C22—H22A | 0.9800 |
C7—C8 | 1.526 (4) | C23—C24 | 1.525 (5) |
C7—H7A | 0.9700 | C23—H23A | 0.9700 |
C7—H7B | 0.9700 | C23—H23B | 0.9700 |
C8—C14 | 1.533 (3) | C24—C28 | 1.511 (4) |
C8—C9 | 1.539 (4) | C24—C25 | 1.537 (4) |
C8—H8A | 0.9800 | C25—C27 | 1.515 (5) |
C9—C11 | 1.541 (4) | C25—C26 | 1.554 (4) |
C9—C10 | 1.570 (3) | C27—H27A | 0.9600 |
C9—H9A | 0.9800 | C27—H27B | 0.9600 |
C10—C19 | 1.553 (4) | C27—H27C | 0.9600 |
C11—C12 | 1.535 (4) | C28—H28A | 0.9600 |
C11—H11A | 0.9700 | C28—H28B | 0.9600 |
C11—H11B | 0.9700 | C28—H28C | 0.9600 |
C12—C13 | 1.522 (4) | C1S—Cl1 | 1.751 (5) |
C12—H12A | 0.9700 | C1S—Cl3 | 1.753 (6) |
C12—H12B | 0.9700 | C1S—Cl2 | 1.758 (5) |
C13—C18 | 1.539 (4) | C1S—H1SA | 0.9800 |
C13—C14 | 1.543 (4) | ||
C26—O2—C22 | 120.5 (2) | C16—C15—H15B | 111.0 |
C24—O3—C20 | 110.5 (2) | H15A—C15—H15B | 109.0 |
C4—O4—H4 | 112 (4) | C15—C16—C17 | 105.8 (2) |
C25—O25—H25 | 109 (4) | C15—C16—H16A | 110.6 |
C5—O56—C6 | 60.70 (19) | C17—C16—H16A | 110.6 |
O1—C1—C2 | 118.9 (3) | C15—C16—H16B | 110.6 |
O1—C1—C10 | 121.9 (3) | C17—C16—H16B | 110.6 |
C2—C1—C10 | 119.2 (3) | H16A—C16—H16B | 108.7 |
C3—C2—C1 | 123.3 (3) | C20—C17—C16 | 114.3 (2) |
C3—C2—H2A | 118.3 | C20—C17—C13 | 121.9 (2) |
C1—C2—H2A | 118.3 | C16—C17—C13 | 103.8 (2) |
C2—C3—C4 | 123.1 (3) | C20—C17—H17A | 105.1 |
C2—C3—H3A | 118.5 | C16—C17—H17A | 105.1 |
C4—C3—H3A | 118.5 | C13—C17—H17A | 105.1 |
O4—C4—C3 | 105.7 (3) | C13—C18—H18A | 109.5 |
O4—C4—C5 | 111.8 (3) | C13—C18—H18B | 109.5 |
C3—C4—C5 | 114.3 (3) | H18A—C18—H18B | 109.5 |
O4—C4—H4B | 108.3 | C13—C18—H18C | 109.5 |
C3—C4—H4B | 108.3 | H18A—C18—H18C | 109.5 |
C5—C4—H4B | 108.3 | H18B—C18—H18C | 109.5 |
O56—C5—C6 | 59.7 (2) | C10—C19—H19A | 109.5 |
O56—C5—C4 | 108.1 (2) | C10—C19—H19B | 109.5 |
C6—C5—C4 | 117.8 (3) | H19A—C19—H19B | 109.5 |
O56—C5—C10 | 116.2 (2) | C10—C19—H19C | 109.5 |
C6—C5—C10 | 121.1 (2) | H19A—C19—H19C | 109.5 |
C4—C5—C10 | 118.2 (3) | H19B—C19—H19C | 109.5 |
O56—C6—C5 | 59.61 (19) | O3—C20—C22 | 101.0 (2) |
O56—C6—C7 | 113.8 (2) | O3—C20—C21 | 108.2 (2) |
C5—C6—C7 | 122.6 (2) | C22—C20—C21 | 110.2 (3) |
O56—C6—H6A | 116.1 | O3—C20—C17 | 105.5 (2) |
C5—C6—H6A | 116.1 | C22—C20—C17 | 115.1 (2) |
C7—C6—H6A | 116.1 | C21—C20—C17 | 115.5 (2) |
C6—C7—C8 | 111.5 (2) | C20—C21—H21A | 109.5 |
C6—C7—H7A | 109.3 | C20—C21—H21B | 109.5 |
C8—C7—H7A | 109.3 | H21A—C21—H21B | 109.5 |
C6—C7—H7B | 109.3 | C20—C21—H21C | 109.5 |
C8—C7—H7B | 109.3 | H21A—C21—H21C | 109.5 |
H7A—C7—H7B | 108.0 | H21B—C21—H21C | 109.5 |
C7—C8—C14 | 109.5 (2) | O2—C22—C23 | 108.6 (2) |
C7—C8—C9 | 110.8 (2) | O2—C22—C20 | 110.4 (2) |
C14—C8—C9 | 107.9 (2) | C23—C22—C20 | 102.6 (3) |
C7—C8—H8A | 109.5 | O2—C22—H22A | 111.6 |
C14—C8—H8A | 109.5 | C23—C22—H22A | 111.6 |
C9—C8—H8A | 109.5 | C20—C22—H22A | 111.6 |
C8—C9—C11 | 111.5 (2) | C22—C23—C24 | 99.3 (2) |
C8—C9—C10 | 114.9 (2) | C22—C23—H23A | 111.9 |
C11—C9—C10 | 112.6 (2) | C24—C23—H23A | 111.9 |
C8—C9—H9A | 105.6 | C22—C23—H23B | 111.9 |
C11—C9—H9A | 105.6 | C24—C23—H23B | 111.9 |
C10—C9—H9A | 105.6 | H23A—C23—H23B | 109.6 |
C5—C10—C1 | 109.0 (2) | O3—C24—C28 | 109.7 (3) |
C5—C10—C19 | 107.0 (2) | O3—C24—C23 | 105.2 (2) |
C1—C10—C19 | 106.1 (3) | C28—C24—C23 | 114.9 (3) |
C5—C10—C9 | 113.1 (2) | O3—C24—C25 | 104.9 (2) |
C1—C10—C9 | 108.2 (2) | C28—C24—C25 | 114.1 (3) |
C19—C10—C9 | 113.2 (2) | C23—C24—C25 | 107.1 (3) |
C12—C11—C9 | 113.0 (2) | O25—C25—C27 | 111.3 (3) |
C12—C11—H11A | 109.0 | O25—C25—C24 | 107.0 (2) |
C9—C11—H11A | 109.0 | C27—C25—C24 | 113.8 (3) |
C12—C11—H11B | 109.0 | O25—C25—C26 | 106.3 (3) |
C9—C11—H11B | 109.0 | C27—C25—C26 | 108.6 (3) |
H11A—C11—H11B | 107.8 | C24—C25—C26 | 109.6 (2) |
C13—C12—C11 | 111.5 (3) | O26—C26—O2 | 117.3 (3) |
C13—C12—H12A | 109.3 | O26—C26—C25 | 121.5 (3) |
C11—C12—H12A | 109.3 | O2—C26—C25 | 121.1 (3) |
C13—C12—H12B | 109.3 | C25—C27—H27A | 109.5 |
C11—C12—H12B | 109.3 | C25—C27—H27B | 109.5 |
H12A—C12—H12B | 108.0 | H27A—C27—H27B | 109.5 |
C12—C13—C18 | 111.1 (3) | C25—C27—H27C | 109.5 |
C12—C13—C14 | 107.2 (2) | H27A—C27—H27C | 109.5 |
C18—C13—C14 | 110.7 (2) | H27B—C27—H27C | 109.5 |
C12—C13—C17 | 116.1 (2) | C24—C28—H28A | 109.5 |
C18—C13—C17 | 112.8 (2) | C24—C28—H28B | 109.5 |
C14—C13—C17 | 98.0 (2) | H28A—C28—H28B | 109.5 |
C8—C14—C15 | 118.9 (2) | C24—C28—H28C | 109.5 |
C8—C14—C13 | 114.5 (2) | H28A—C28—H28C | 109.5 |
C15—C14—C13 | 104.6 (2) | H28B—C28—H28C | 109.5 |
C8—C14—H14A | 106.0 | Cl1—C1S—Cl3 | 110.3 (3) |
C15—C14—H14A | 106.0 | Cl1—C1S—Cl2 | 110.3 (3) |
C13—C14—H14A | 106.0 | Cl3—C1S—Cl2 | 109.7 (3) |
C14—C15—C16 | 104.0 (2) | Cl1—C1S—H1SA | 108.8 |
C14—C15—H15A | 111.0 | Cl3—C1S—H1SA | 108.8 |
C16—C15—H15A | 111.0 | Cl2—C1S—H1SA | 108.8 |
C14—C15—H15B | 111.0 | ||
O1—C1—C2—C3 | 168.0 (4) | C18—C13—C14—C8 | 61.1 (3) |
C10—C1—C2—C3 | −13.6 (6) | C17—C13—C14—C8 | 179.2 (2) |
C1—C2—C3—C4 | 1.4 (7) | C12—C13—C14—C15 | 167.9 (2) |
C2—C3—C4—O4 | 113.0 (4) | C18—C13—C14—C15 | −70.8 (3) |
C2—C3—C4—C5 | −10.3 (6) | C17—C13—C14—C15 | 47.4 (3) |
C6—O56—C5—C4 | 112.2 (3) | C8—C14—C15—C16 | −161.5 (3) |
C6—O56—C5—C10 | −112.2 (3) | C13—C14—C15—C16 | −32.3 (3) |
O4—C4—C5—O56 | 46.6 (4) | C14—C15—C16—C17 | 3.4 (3) |
C3—C4—C5—O56 | 166.5 (3) | C15—C16—C17—C20 | 161.1 (3) |
O4—C4—C5—C6 | 111.2 (3) | C15—C16—C17—C13 | 26.1 (3) |
C3—C4—C5—C6 | −128.8 (3) | C12—C13—C17—C20 | 71.2 (3) |
O4—C4—C5—C10 | −88.0 (4) | C18—C13—C17—C20 | −58.6 (4) |
C3—C4—C5—C10 | 32.0 (4) | C14—C13—C17—C20 | −175.1 (2) |
C5—O56—C6—C7 | 115.1 (3) | C12—C13—C17—C16 | −158.1 (3) |
C4—C5—C6—O56 | −95.6 (3) | C18—C13—C17—C16 | 72.1 (3) |
C10—C5—C6—O56 | 104.1 (3) | C14—C13—C17—C16 | −44.4 (3) |
O56—C5—C6—C7 | −100.4 (3) | C24—O3—C20—C22 | 18.6 (3) |
C4—C5—C6—C7 | 164.0 (3) | C24—O3—C20—C21 | −97.2 (3) |
C10—C5—C6—C7 | 3.8 (5) | C24—O3—C20—C17 | 138.7 (2) |
O56—C6—C7—C8 | −43.7 (3) | C16—C17—C20—O3 | 56.0 (3) |
C5—C6—C7—C8 | 24.3 (4) | C13—C17—C20—O3 | −177.9 (2) |
C6—C7—C8—C14 | −172.2 (2) | C16—C17—C20—C22 | 166.4 (2) |
C6—C7—C8—C9 | −53.3 (3) | C13—C17—C20—C22 | −67.5 (3) |
C7—C8—C9—C11 | −173.0 (2) | C16—C17—C20—C21 | −63.3 (4) |
C14—C8—C9—C11 | −53.1 (3) | C13—C17—C20—C21 | 62.7 (4) |
C7—C8—C9—C10 | 57.3 (3) | C26—O2—C22—C23 | 38.6 (4) |
C14—C8—C9—C10 | 177.2 (2) | C26—O2—C22—C20 | −73.1 (3) |
O56—C5—C10—C1 | −172.3 (2) | O3—C20—C22—O2 | 75.4 (3) |
C6—C5—C10—C1 | 118.8 (3) | C21—C20—C22—O2 | −170.3 (2) |
C4—C5—C10—C1 | −41.4 (4) | C17—C20—C22—O2 | −37.6 (3) |
O56—C5—C10—C19 | −58.1 (3) | O3—C20—C22—C23 | −40.2 (3) |
C6—C5—C10—C19 | −126.9 (3) | C21—C20—C22—C23 | 74.1 (3) |
C4—C5—C10—C19 | 72.9 (3) | C17—C20—C22—C23 | −153.2 (2) |
O56—C5—C10—C9 | 67.3 (3) | O2—C22—C23—C24 | −71.4 (3) |
C6—C5—C10—C9 | −1.6 (4) | C20—C22—C23—C24 | 45.4 (3) |
C4—C5—C10—C9 | −161.8 (3) | C20—O3—C24—C28 | 133.8 (3) |
O1—C1—C10—C5 | −149.7 (4) | C20—O3—C24—C23 | 9.7 (3) |
C2—C1—C10—C5 | 32.0 (4) | C20—O3—C24—C25 | −103.1 (3) |
O1—C1—C10—C19 | 95.4 (4) | C22—C23—C24—O3 | −34.1 (3) |
C2—C1—C10—C19 | −82.9 (4) | C22—C23—C24—C28 | −154.9 (3) |
O1—C1—C10—C9 | −26.4 (5) | C22—C23—C24—C25 | 77.2 (3) |
C2—C1—C10—C9 | 155.4 (3) | O3—C24—C25—O25 | 178.9 (3) |
C8—C9—C10—C5 | −28.7 (3) | C28—C24—C25—O25 | −60.9 (4) |
C11—C9—C10—C5 | −157.8 (2) | C23—C24—C25—O25 | 67.4 (3) |
C8—C9—C10—C1 | −149.5 (2) | O3—C24—C25—C27 | −57.7 (3) |
C11—C9—C10—C1 | 81.3 (3) | C28—C24—C25—C27 | 62.4 (4) |
C8—C9—C10—C19 | 93.2 (3) | C23—C24—C25—C27 | −169.3 (3) |
C11—C9—C10—C19 | −35.9 (3) | O3—C24—C25—C26 | 64.1 (3) |
C8—C9—C11—C12 | 53.6 (3) | C28—C24—C25—C26 | −175.8 (3) |
C10—C9—C11—C12 | −175.6 (3) | C23—C24—C25—C26 | −47.4 (3) |
C9—C11—C12—C13 | −55.3 (4) | C22—O2—C26—O26 | 176.1 (3) |
C11—C12—C13—C18 | −65.2 (3) | C22—O2—C26—C25 | −7.0 (4) |
C11—C12—C13—C14 | 55.9 (3) | O25—C25—C26—O26 | 72.9 (4) |
C11—C12—C13—C17 | 164.2 (3) | C27—C25—C26—O26 | −46.8 (4) |
C7—C8—C14—C15 | −55.9 (3) | C24—C25—C26—O26 | −171.7 (3) |
C9—C8—C14—C15 | −176.6 (3) | O25—C25—C26—O2 | −103.9 (3) |
C7—C8—C14—C13 | 179.6 (2) | C27—C25—C26—O2 | 136.4 (3) |
C9—C8—C14—C13 | 58.9 (3) | C24—C25—C26—O2 | 11.5 (4) |
C12—C13—C14—C8 | −60.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O26i | 0.79 (6) | 2.10 (6) | 2.819 (4) | 151 |
O25—H25···O56ii | 0.74 (5) | 2.12 (5) | 2.856 (4) | 169 |
C23—H23A···O26iii | 0.97 | 2.57 | 3.473 (4) | 154 |
C1S—H1SA···O26 | 0.98 | 2.43 | 3.393 (6) | 168 |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1; (iii) x+1, y, z. |
C28H40O7 | F(000) = 264 |
Mr = 488.60 | Dx = 1.312 Mg m−3 |
Triclinic, P1 | Melting point: 528(3) K |
a = 6.2374 (12) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 9.5938 (19) Å | Cell parameters from 1941 reflections |
c = 11.351 (2) Å | θ = 4.3–75.5° |
α = 112.81 (3)° | µ = 0.76 mm−1 |
β = 96.49 (3)° | T = 290 K |
γ = 93.13 (3)° | Prizmatic, colorless |
V = 618.5 (2) Å3 | 0.42 × 0.28 × 0.21 mm |
Z = 1 |
Rigaku Xcalibur, Ruby diffractometer | 2812 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2545 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 10.2576 pixels mm-1 | θmax = 76.7°, θmin = 4.3° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −12→11 |
Tmin = 0.776, Tmax = 0.853 | l = −14→10 |
4169 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0647P)2 + 0.0383P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.110 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.17 e Å−3 |
2812 reflections | Δρmin = −0.19 e Å−3 |
333 parameters | Absolute structure: Classical Flack method preferred over Parsons because s.u. lower. |
3 restraints | Absolute structure parameter: −0.1 (2) |
Primary atom site location: structure-invariant direct methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.0734 (4) | 1.2216 (4) | 0.3845 (3) | 0.0674 (8) | |
O2 | 1.0070 (4) | 0.6040 (2) | 0.9120 (2) | 0.0441 (5) | |
O5 | 0.8575 (4) | 0.8791 (3) | 0.0969 (2) | 0.0524 (6) | |
O14 | 0.9050 (4) | 0.6585 (3) | 0.3671 (2) | 0.0468 (5) | |
O20 | 0.7306 (4) | 0.7378 (3) | 0.8118 (2) | 0.0444 (5) | |
O26 | 1.0412 (5) | 0.5281 (3) | 1.0706 (2) | 0.0591 (7) | |
O67 | 0.6045 (4) | 0.6709 (3) | 0.1319 (2) | 0.0555 (6) | |
C1 | 0.9157 (5) | 1.1689 (4) | 0.3017 (3) | 0.0431 (7) | |
C2 | 0.8775 (6) | 1.2312 (5) | 0.2017 (4) | 0.0551 (9) | |
H2A | 0.9624 | 1.3185 | 0.2108 | 0.066* | |
C3 | 0.7256 (6) | 1.1664 (5) | 0.0993 (4) | 0.0605 (10) | |
H3A | 0.7103 | 1.2095 | 0.0387 | 0.073* | |
C4 | 0.5794 (6) | 1.0290 (4) | 0.0768 (3) | 0.0534 (8) | |
H4A | 0.5570 | 0.9639 | −0.0146 | 0.064* | |
H4B | 0.4396 | 1.0589 | 0.1014 | 0.064* | |
C5 | 0.6713 (5) | 0.9395 (4) | 0.1537 (3) | 0.0417 (7) | |
C6 | 0.5077 (6) | 0.8077 (4) | 0.1384 (3) | 0.0472 (7) | |
H6A | 0.3725 | 0.7928 | 0.0798 | 0.057* | |
C7 | 0.4970 (5) | 0.7531 (4) | 0.2412 (3) | 0.0444 (7) | |
H7A | 0.3550 | 0.7054 | 0.2427 | 0.053* | |
C8 | 0.6366 (4) | 0.8339 (3) | 0.3704 (3) | 0.0346 (6) | |
H8A | 0.5414 | 0.8946 | 0.4290 | 0.042* | |
C9 | 0.8236 (5) | 0.9479 (3) | 0.3713 (3) | 0.0357 (6) | |
H9A | 0.9315 | 0.8878 | 0.3238 | 0.043* | |
C10 | 0.7426 (5) | 1.0460 (3) | 0.2988 (3) | 0.0358 (6) | |
C11 | 0.9330 (6) | 1.0353 (4) | 0.5127 (3) | 0.0535 (9) | |
H11A | 1.0577 | 1.1011 | 0.5140 | 0.064* | |
H11B | 0.8316 | 1.0994 | 0.5613 | 0.064* | |
C12 | 1.0074 (5) | 0.9316 (4) | 0.5799 (3) | 0.0490 (8) | |
H12A | 1.0653 | 0.9934 | 0.6694 | 0.059* | |
H12B | 1.1229 | 0.8769 | 0.5387 | 0.059* | |
C13 | 0.8206 (4) | 0.8163 (3) | 0.5748 (3) | 0.0343 (6) | |
C14 | 0.7262 (4) | 0.7268 (3) | 0.4299 (3) | 0.0360 (6) | |
C15 | 0.5738 (5) | 0.5985 (4) | 0.4314 (3) | 0.0471 (7) | |
H15A | 0.5507 | 0.5132 | 0.3481 | 0.056* | |
H15B | 0.4347 | 0.6329 | 0.4535 | 0.056* | |
C16 | 0.6930 (5) | 0.5546 (4) | 0.5361 (3) | 0.0451 (7) | |
H16A | 0.7500 | 0.4576 | 0.4966 | 0.054* | |
H16B | 0.5941 | 0.5457 | 0.5935 | 0.054* | |
C17 | 0.8822 (4) | 0.6823 (3) | 0.6131 (3) | 0.0353 (6) | |
H17A | 1.0134 | 0.6476 | 0.5756 | 0.042* | |
C18 | 0.6480 (6) | 0.9019 (4) | 0.6520 (3) | 0.0478 (7) | |
H18A | 0.5306 | 0.8303 | 0.6479 | 0.072* | |
H18B | 0.5940 | 0.9709 | 0.6161 | 0.072* | |
H18C | 0.7113 | 0.9579 | 0.7405 | 0.072* | |
C19 | 0.5529 (5) | 1.1315 (4) | 0.3550 (3) | 0.0459 (7) | |
H19A | 0.5891 | 1.1821 | 0.4472 | 0.069* | |
H19B | 0.4257 | 1.0605 | 0.3342 | 0.069* | |
H19C | 0.5250 | 1.2052 | 0.3189 | 0.069* | |
C20 | 0.9287 (5) | 0.7102 (3) | 0.7577 (3) | 0.0367 (6) | |
C21 | 1.0997 (5) | 0.8455 (4) | 0.8335 (3) | 0.0458 (7) | |
H21A | 1.0430 | 0.9375 | 0.8361 | 0.069* | |
H21B | 1.2274 | 0.8323 | 0.7921 | 0.069* | |
H21C | 1.1360 | 0.8517 | 0.9200 | 0.069* | |
C22 | 1.0006 (5) | 0.5651 (3) | 0.7731 (3) | 0.0378 (6) | |
H22A | 0.8854 | 0.4817 | 0.7265 | 0.045* | |
C23 | 1.2147 (6) | 0.5111 (4) | 0.7296 (3) | 0.0461 (7) | |
H23A | 1.3111 | 0.5980 | 0.7375 | 0.055* | |
H23B | 1.1877 | 0.4423 | 0.6392 | 0.055* | |
C24 | 1.3270 (5) | 0.4300 (3) | 0.8076 (3) | 0.0404 (6) | |
H24A | 1.4316 | 0.5062 | 0.8766 | 0.048* | |
C25 | 1.1654 (5) | 0.3683 (4) | 0.8731 (3) | 0.0430 (7) | |
H25A | 1.0508 | 0.3003 | 0.8057 | 0.052* | |
C26 | 1.0632 (5) | 0.5015 (4) | 0.9602 (3) | 0.0414 (7) | |
C27 | 1.2617 (7) | 0.2800 (5) | 0.9482 (4) | 0.0610 (9) | |
H27A | 1.1503 | 0.2463 | 0.9859 | 0.091* | |
H27B | 1.3742 | 0.3445 | 1.0153 | 0.091* | |
H27C | 1.3216 | 0.1935 | 0.8909 | 0.091* | |
C28 | 1.4558 (6) | 0.3074 (4) | 0.7249 (4) | 0.0525 (8) | |
H28A | 1.5525 | 0.2760 | 0.7797 | 0.079* | |
H28B | 1.5384 | 0.3474 | 0.6764 | 0.079* | |
H28C | 1.3576 | 0.2216 | 0.6666 | 0.079* | |
H5 | 0.858 (7) | 0.793 (6) | 0.113 (4) | 0.069 (13)* | |
H14 | 0.884 (8) | 0.628 (6) | 0.289 (5) | 0.069 (14)* | |
H20 | 0.768 (9) | 0.767 (7) | 0.884 (6) | 0.09 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0566 (14) | 0.0798 (18) | 0.0761 (19) | −0.0157 (13) | −0.0101 (13) | 0.0506 (16) |
O2 | 0.0575 (13) | 0.0457 (12) | 0.0372 (11) | 0.0172 (10) | 0.0157 (9) | 0.0214 (10) |
O5 | 0.0675 (15) | 0.0570 (15) | 0.0387 (12) | 0.0261 (12) | 0.0205 (10) | 0.0197 (11) |
O14 | 0.0572 (14) | 0.0504 (13) | 0.0346 (12) | 0.0207 (11) | 0.0123 (10) | 0.0153 (10) |
O20 | 0.0445 (12) | 0.0573 (14) | 0.0371 (12) | 0.0169 (10) | 0.0125 (9) | 0.0218 (11) |
O26 | 0.0718 (17) | 0.0731 (17) | 0.0456 (14) | 0.0210 (13) | 0.0187 (12) | 0.0335 (13) |
O67 | 0.0801 (17) | 0.0401 (12) | 0.0352 (12) | 0.0108 (11) | −0.0037 (11) | 0.0057 (9) |
C1 | 0.0428 (16) | 0.0457 (17) | 0.0456 (17) | 0.0093 (13) | 0.0078 (13) | 0.0222 (14) |
C2 | 0.059 (2) | 0.058 (2) | 0.063 (2) | 0.0067 (16) | 0.0102 (17) | 0.0395 (19) |
C3 | 0.070 (2) | 0.071 (2) | 0.059 (2) | 0.0197 (19) | 0.0074 (18) | 0.044 (2) |
C4 | 0.065 (2) | 0.059 (2) | 0.0408 (17) | 0.0164 (17) | −0.0008 (15) | 0.0253 (16) |
C5 | 0.0501 (17) | 0.0462 (17) | 0.0301 (14) | 0.0166 (14) | 0.0064 (12) | 0.0148 (13) |
C6 | 0.0545 (18) | 0.0424 (17) | 0.0366 (15) | 0.0054 (13) | −0.0093 (13) | 0.0112 (13) |
C7 | 0.0449 (16) | 0.0414 (17) | 0.0397 (16) | 0.0014 (13) | −0.0063 (13) | 0.0121 (13) |
C8 | 0.0354 (14) | 0.0361 (14) | 0.0293 (14) | 0.0030 (11) | 0.0002 (11) | 0.0110 (11) |
C9 | 0.0377 (14) | 0.0393 (15) | 0.0300 (13) | 0.0042 (11) | 0.0031 (10) | 0.0142 (12) |
C10 | 0.0387 (14) | 0.0382 (14) | 0.0315 (13) | 0.0074 (11) | 0.0057 (10) | 0.0145 (11) |
C11 | 0.070 (2) | 0.0465 (18) | 0.0395 (17) | −0.0196 (16) | −0.0160 (16) | 0.0223 (15) |
C12 | 0.0541 (19) | 0.0528 (19) | 0.0384 (16) | −0.0158 (15) | −0.0106 (13) | 0.0238 (15) |
C13 | 0.0405 (15) | 0.0327 (13) | 0.0299 (13) | 0.0017 (11) | 0.0014 (11) | 0.0141 (11) |
C14 | 0.0381 (14) | 0.0351 (14) | 0.0305 (14) | 0.0032 (11) | 0.0030 (11) | 0.0090 (11) |
C15 | 0.0500 (18) | 0.0387 (15) | 0.0466 (17) | −0.0078 (13) | −0.0078 (13) | 0.0161 (14) |
C16 | 0.0537 (18) | 0.0377 (16) | 0.0410 (16) | −0.0037 (13) | 0.0007 (13) | 0.0153 (13) |
C17 | 0.0382 (14) | 0.0354 (14) | 0.0321 (14) | 0.0030 (11) | 0.0067 (11) | 0.0128 (12) |
C18 | 0.065 (2) | 0.0458 (17) | 0.0371 (16) | 0.0202 (15) | 0.0126 (14) | 0.0179 (14) |
C19 | 0.0497 (18) | 0.0423 (16) | 0.0476 (18) | 0.0135 (14) | 0.0146 (14) | 0.0167 (14) |
C20 | 0.0390 (14) | 0.0392 (14) | 0.0313 (14) | 0.0046 (11) | 0.0066 (11) | 0.0130 (12) |
C21 | 0.0556 (19) | 0.0444 (16) | 0.0356 (15) | −0.0026 (14) | −0.0020 (13) | 0.0171 (13) |
C22 | 0.0416 (15) | 0.0408 (15) | 0.0311 (14) | 0.0043 (12) | 0.0054 (11) | 0.0145 (12) |
C23 | 0.0491 (17) | 0.0510 (18) | 0.0441 (17) | 0.0133 (14) | 0.0138 (13) | 0.0223 (15) |
C24 | 0.0429 (15) | 0.0365 (14) | 0.0404 (15) | 0.0057 (12) | 0.0044 (12) | 0.0141 (12) |
C25 | 0.0443 (15) | 0.0414 (16) | 0.0460 (17) | 0.0057 (12) | 0.0047 (13) | 0.0207 (14) |
C26 | 0.0421 (15) | 0.0464 (17) | 0.0419 (16) | 0.0052 (13) | 0.0091 (12) | 0.0235 (14) |
C27 | 0.075 (2) | 0.055 (2) | 0.068 (2) | 0.0181 (19) | 0.0158 (19) | 0.0374 (19) |
C28 | 0.0481 (17) | 0.0475 (18) | 0.063 (2) | 0.0124 (14) | 0.0125 (15) | 0.0211 (16) |
O1—C1 | 1.214 (4) | C13—C18 | 1.534 (4) |
O2—C26 | 1.341 (4) | C13—C14 | 1.555 (4) |
O2—C22 | 1.468 (3) | C13—C17 | 1.562 (4) |
O5—C5 | 1.433 (4) | C14—C15 | 1.520 (4) |
O5—H5 | 0.92 (5) | C15—C16 | 1.538 (5) |
O14—C14 | 1.442 (4) | C15—H15A | 0.9700 |
O14—H14 | 0.81 (5) | C15—H15B | 0.9700 |
O20—C20 | 1.434 (4) | C16—C17 | 1.561 (4) |
O20—H20 | 0.76 (6) | C16—H16A | 0.9700 |
O26—C26 | 1.204 (4) | C16—H16B | 0.9700 |
O67—C7 | 1.448 (4) | C17—C20 | 1.546 (4) |
O67—C6 | 1.454 (4) | C17—H17A | 0.9800 |
C1—C2 | 1.478 (5) | C18—H18A | 0.9600 |
C1—C10 | 1.542 (4) | C18—H18B | 0.9600 |
C2—C3 | 1.327 (6) | C18—H18C | 0.9600 |
C2—H2A | 0.9300 | C19—H19A | 0.9600 |
C3—C4 | 1.480 (6) | C19—H19B | 0.9600 |
C3—H3A | 0.9300 | C19—H19C | 0.9600 |
C4—C5 | 1.532 (4) | C20—C21 | 1.530 (4) |
C4—H4A | 0.9700 | C20—C22 | 1.552 (4) |
C4—H4B | 0.9700 | C21—H21A | 0.9600 |
C5—C6 | 1.523 (5) | C21—H21B | 0.9600 |
C5—C10 | 1.560 (4) | C21—H21C | 0.9600 |
C6—C7 | 1.458 (5) | C22—C23 | 1.523 (4) |
C6—H6A | 0.9800 | C22—H22A | 0.9800 |
C7—C8 | 1.506 (4) | C23—C24 | 1.527 (5) |
C7—H7A | 0.9800 | C23—H23A | 0.9700 |
C8—C14 | 1.530 (4) | C23—H23B | 0.9700 |
C8—C9 | 1.551 (4) | C24—C28 | 1.526 (5) |
C8—H8A | 0.9800 | C24—C25 | 1.539 (4) |
C9—C10 | 1.542 (4) | C24—H24A | 0.9800 |
C9—C11 | 1.546 (4) | C25—C26 | 1.507 (5) |
C9—H9A | 0.9800 | C25—C27 | 1.518 (5) |
C10—C19 | 1.534 (4) | C25—H25A | 0.9800 |
C11—C12 | 1.532 (5) | C27—H27A | 0.9600 |
C11—H11A | 0.9700 | C27—H27B | 0.9600 |
C11—H11B | 0.9700 | C27—H27C | 0.9600 |
C12—C13 | 1.542 (4) | C28—H28A | 0.9600 |
C12—H12A | 0.9700 | C28—H28B | 0.9600 |
C12—H12B | 0.9700 | C28—H28C | 0.9600 |
C26—O2—C22 | 119.2 (2) | C14—C15—H15A | 111.0 |
C5—O5—H5 | 100 (3) | C16—C15—H15A | 111.0 |
C14—O14—H14 | 114 (3) | C14—C15—H15B | 111.0 |
C20—O20—H20 | 103 (4) | C16—C15—H15B | 111.0 |
C7—O67—C6 | 60.3 (2) | H15A—C15—H15B | 109.0 |
O1—C1—C2 | 118.9 (3) | C15—C16—C17 | 107.5 (2) |
O1—C1—C10 | 123.8 (3) | C15—C16—H16A | 110.2 |
C2—C1—C10 | 117.1 (3) | C17—C16—H16A | 110.2 |
C3—C2—C1 | 122.0 (3) | C15—C16—H16B | 110.2 |
C3—C2—H2A | 119.0 | C17—C16—H16B | 110.2 |
C1—C2—H2A | 119.0 | H16A—C16—H16B | 108.5 |
C2—C3—C4 | 123.3 (3) | C20—C17—C16 | 113.2 (2) |
C2—C3—H3A | 118.3 | C20—C17—C13 | 119.4 (2) |
C4—C3—H3A | 118.3 | C16—C17—C13 | 103.1 (2) |
C3—C4—C5 | 112.1 (3) | C20—C17—H17A | 106.8 |
C3—C4—H4A | 109.2 | C16—C17—H17A | 106.8 |
C5—C4—H4A | 109.2 | C13—C17—H17A | 106.8 |
C3—C4—H4B | 109.2 | C13—C18—H18A | 109.5 |
C5—C4—H4B | 109.2 | C13—C18—H18B | 109.5 |
H4A—C4—H4B | 107.9 | H18A—C18—H18B | 109.5 |
O5—C5—C6 | 108.7 (3) | C13—C18—H18C | 109.5 |
O5—C5—C4 | 105.4 (3) | H18A—C18—H18C | 109.5 |
C6—C5—C4 | 110.6 (3) | H18B—C18—H18C | 109.5 |
O5—C5—C10 | 109.5 (2) | C10—C19—H19A | 109.5 |
C6—C5—C10 | 111.4 (2) | C10—C19—H19B | 109.5 |
C4—C5—C10 | 111.0 (3) | H19A—C19—H19B | 109.5 |
O67—C6—C7 | 59.6 (2) | C10—C19—H19C | 109.5 |
O67—C6—C5 | 114.1 (3) | H19A—C19—H19C | 109.5 |
C7—C6—C5 | 121.6 (3) | H19B—C19—H19C | 109.5 |
O67—C6—H6A | 116.3 | O20—C20—C21 | 109.3 (3) |
C7—C6—H6A | 116.3 | O20—C20—C17 | 108.7 (2) |
C5—C6—H6A | 116.3 | C21—C20—C17 | 112.1 (2) |
O67—C7—C6 | 60.0 (2) | O20—C20—C22 | 105.9 (2) |
O67—C7—C8 | 117.5 (3) | C21—C20—C22 | 110.1 (2) |
C6—C7—C8 | 120.6 (3) | C17—C20—C22 | 110.5 (2) |
O67—C7—H7A | 115.7 | C20—C21—H21A | 109.5 |
C6—C7—H7A | 115.7 | C20—C21—H21B | 109.5 |
C8—C7—H7A | 115.7 | H21A—C21—H21B | 109.5 |
C7—C8—C14 | 113.8 (2) | C20—C21—H21C | 109.5 |
C7—C8—C9 | 114.2 (2) | H21A—C21—H21C | 109.5 |
C14—C8—C9 | 109.8 (2) | H21B—C21—H21C | 109.5 |
C7—C8—H8A | 106.1 | O2—C22—C23 | 110.7 (2) |
C14—C8—H8A | 106.1 | O2—C22—C20 | 103.0 (2) |
C9—C8—H8A | 106.1 | C23—C22—C20 | 118.2 (2) |
C10—C9—C11 | 116.2 (2) | O2—C22—H22A | 108.2 |
C10—C9—C8 | 111.0 (2) | C23—C22—H22A | 108.2 |
C11—C9—C8 | 108.0 (2) | C20—C22—H22A | 108.2 |
C10—C9—H9A | 107.1 | C22—C23—C24 | 113.1 (3) |
C11—C9—H9A | 107.1 | C22—C23—H23A | 109.0 |
C8—C9—H9A | 107.1 | C24—C23—H23A | 109.0 |
C19—C10—C9 | 111.9 (2) | C22—C23—H23B | 109.0 |
C19—C10—C1 | 105.6 (2) | C24—C23—H23B | 109.0 |
C9—C10—C1 | 114.3 (2) | H23A—C23—H23B | 107.8 |
C19—C10—C5 | 110.1 (2) | C28—C24—C23 | 111.1 (3) |
C9—C10—C5 | 108.3 (2) | C28—C24—C25 | 112.6 (3) |
C1—C10—C5 | 106.5 (2) | C23—C24—C25 | 111.5 (3) |
C12—C11—C9 | 113.7 (3) | C28—C24—H24A | 107.1 |
C12—C11—H11A | 108.8 | C23—C24—H24A | 107.1 |
C9—C11—H11A | 108.8 | C25—C24—H24A | 107.1 |
C12—C11—H11B | 108.8 | C26—C25—C27 | 110.4 (3) |
C9—C11—H11B | 108.8 | C26—C25—C24 | 107.4 (2) |
H11A—C11—H11B | 107.7 | C27—C25—C24 | 115.1 (3) |
C11—C12—C13 | 112.1 (3) | C26—C25—H25A | 107.9 |
C11—C12—H12A | 109.2 | C27—C25—H25A | 107.9 |
C13—C12—H12A | 109.2 | C24—C25—H25A | 107.9 |
C11—C12—H12B | 109.2 | O26—C26—O2 | 118.0 (3) |
C13—C12—H12B | 109.2 | O26—C26—C25 | 125.7 (3) |
H12A—C12—H12B | 107.9 | O2—C26—C25 | 116.2 (3) |
C18—C13—C12 | 109.4 (3) | C25—C27—H27A | 109.5 |
C18—C13—C14 | 111.2 (2) | C25—C27—H27B | 109.5 |
C12—C13—C14 | 106.9 (2) | H27A—C27—H27B | 109.5 |
C18—C13—C17 | 111.2 (2) | C25—C27—H27C | 109.5 |
C12—C13—C17 | 117.4 (2) | H27A—C27—H27C | 109.5 |
C14—C13—C17 | 100.3 (2) | H27B—C27—H27C | 109.5 |
O14—C14—C15 | 107.0 (2) | C24—C28—H28A | 109.5 |
O14—C14—C8 | 109.7 (2) | C24—C28—H28B | 109.5 |
C15—C14—C8 | 119.1 (2) | H28A—C28—H28B | 109.5 |
O14—C14—C13 | 105.9 (2) | C24—C28—H28C | 109.5 |
C15—C14—C13 | 103.5 (2) | H28A—C28—H28C | 109.5 |
C8—C14—C13 | 110.8 (2) | H28B—C28—H28C | 109.5 |
C14—C15—C16 | 103.8 (2) | ||
O1—C1—C2—C3 | 171.0 (4) | C9—C8—C14—O14 | −52.5 (3) |
C10—C1—C2—C3 | −12.6 (5) | C7—C8—C14—C15 | −46.7 (4) |
C1—C2—C3—C4 | 1.1 (6) | C9—C8—C14—C15 | −176.2 (3) |
C2—C3—C4—C5 | −20.5 (6) | C7—C8—C14—C13 | −166.4 (3) |
C3—C4—C5—O5 | −68.1 (4) | C9—C8—C14—C13 | 64.1 (3) |
C3—C4—C5—C6 | 174.6 (3) | C18—C13—C14—O14 | 177.1 (2) |
C3—C4—C5—C10 | 50.3 (4) | C12—C13—C14—O14 | 57.8 (3) |
C7—O67—C6—C5 | 113.8 (3) | C17—C13—C14—O14 | −65.2 (3) |
O5—C5—C6—O67 | 27.8 (3) | C18—C13—C14—C15 | −70.5 (3) |
C4—C5—C6—O67 | 143.1 (3) | C12—C13—C14—C15 | 170.1 (3) |
C10—C5—C6—O67 | −92.9 (3) | C17—C13—C14—C15 | 47.2 (3) |
O5—C5—C6—C7 | 95.8 (4) | C18—C13—C14—C8 | 58.2 (3) |
C4—C5—C6—C7 | −148.9 (3) | C12—C13—C14—C8 | −61.2 (3) |
C10—C5—C6—C7 | −25.0 (4) | C17—C13—C14—C8 | 175.9 (2) |
C6—O67—C7—C8 | −111.3 (3) | O14—C14—C15—C16 | 74.2 (3) |
C5—C6—C7—O67 | −101.2 (3) | C8—C14—C15—C16 | −160.8 (3) |
O67—C6—C7—C8 | 106.1 (3) | C13—C14—C15—C16 | −37.3 (3) |
C5—C6—C7—C8 | 4.9 (5) | C14—C15—C16—C17 | 13.0 (3) |
O67—C7—C8—C14 | −71.8 (3) | C15—C16—C17—C20 | 146.3 (3) |
C6—C7—C8—C14 | −141.6 (3) | C15—C16—C17—C13 | 16.0 (3) |
O67—C7—C8—C9 | 55.4 (4) | C18—C13—C17—C20 | −46.5 (3) |
C6—C7—C8—C9 | −14.4 (4) | C12—C13—C17—C20 | 80.5 (3) |
C7—C8—C9—C10 | 44.7 (3) | C14—C13—C17—C20 | −164.2 (2) |
C14—C8—C9—C10 | 173.9 (2) | C18—C13—C17—C16 | 79.9 (3) |
C7—C8—C9—C11 | 173.1 (3) | C12—C13—C17—C16 | −153.1 (3) |
C14—C8—C9—C11 | −57.7 (3) | C14—C13—C17—C16 | −37.8 (3) |
C11—C9—C10—C19 | −67.2 (3) | C16—C17—C20—O20 | −53.7 (3) |
C8—C9—C10—C19 | 56.7 (3) | C13—C17—C20—O20 | 67.9 (3) |
C11—C9—C10—C1 | 52.9 (4) | C16—C17—C20—C21 | −174.6 (3) |
C8—C9—C10—C1 | 176.7 (2) | C13—C17—C20—C21 | −53.1 (3) |
C11—C9—C10—C5 | 171.4 (3) | C16—C17—C20—C22 | 62.1 (3) |
C8—C9—C10—C5 | −64.8 (3) | C13—C17—C20—C22 | −176.3 (2) |
O1—C1—C10—C19 | 99.7 (4) | C26—O2—C22—C23 | −53.1 (3) |
C2—C1—C10—C19 | −76.5 (4) | C26—O2—C22—C20 | 179.6 (2) |
O1—C1—C10—C9 | −23.8 (5) | O20—C20—C22—O2 | −54.7 (3) |
C2—C1—C10—C9 | 160.0 (3) | C21—C20—C22—O2 | 63.4 (3) |
O1—C1—C10—C5 | −143.3 (4) | C17—C20—C22—O2 | −172.2 (2) |
C2—C1—C10—C5 | 40.5 (4) | O20—C20—C22—C23 | −177.1 (3) |
O5—C5—C10—C19 | 170.9 (3) | C21—C20—C22—C23 | −59.1 (3) |
C6—C5—C10—C19 | −68.9 (3) | C17—C20—C22—C23 | 65.4 (3) |
C4—C5—C10—C19 | 54.9 (3) | O2—C22—C23—C24 | 31.1 (4) |
O5—C5—C10—C9 | −66.6 (3) | C20—C22—C23—C24 | 149.5 (3) |
C6—C5—C10—C9 | 53.7 (3) | C22—C23—C24—C28 | 148.4 (3) |
C4—C5—C10—C9 | 177.5 (3) | C22—C23—C24—C25 | 21.9 (4) |
O5—C5—C10—C1 | 56.8 (3) | C28—C24—C25—C26 | 175.2 (3) |
C6—C5—C10—C1 | 177.1 (3) | C23—C24—C25—C26 | −59.1 (3) |
C4—C5—C10—C1 | −59.1 (3) | C28—C24—C25—C27 | 51.8 (4) |
C10—C9—C11—C12 | 179.3 (3) | C23—C24—C25—C27 | 177.5 (3) |
C8—C9—C11—C12 | 53.9 (4) | C22—O2—C26—O26 | −170.9 (3) |
C9—C11—C12—C13 | −55.1 (4) | C22—O2—C26—C25 | 13.8 (4) |
C11—C12—C13—C18 | −64.7 (3) | C27—C25—C26—O26 | −6.5 (5) |
C11—C12—C13—C14 | 55.8 (3) | C24—C25—C26—O26 | −132.7 (3) |
C11—C12—C13—C17 | 167.4 (3) | C27—C25—C26—O2 | 168.4 (3) |
C7—C8—C14—O14 | 76.9 (3) | C24—C25—C26—O2 | 42.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O20—H20···O5i | 0.76 (6) | 2.22 (6) | 2.973 (4) | 173 |
C7—H7A···O26ii | 0.98 | 2.59 | 3.367 (5) | 136 |
Symmetry codes: (i) x, y, z+1; (ii) x−1, y, z−1. |
Acknowledgements
We are especially grateful to Dr Kambarali Turgunov for help in discussing the results.
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