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Two isomeric cucurbitane derivatives, 3β,7α,11β-triacetoxycucurbit-5(10)-ene, (I), and 3β,7α,11β-triacetoxy-5α-cucurbit-1(10)-ene, (II), both C36H58O6, have their single endocyclic C=C double bonds in different positions. This results in differences in the conformation of the four-ring system, which is close to a half-chair/half-chair/chair/half-chair arrangement in (I) and to a half-chair/twist-boat/boat/half-chair arrangement in (II). The orientation of some of the substituents is also different; the 3β-acetoxy group is in an equatorial position in (I) but in an axial position in (II), while the 11β-acetoxy group occupies an axial position in (I) and an equatorial position in (II). The asymmetric unit of (I) contains two symmetry-independent molecules which do not differ significantly, being related by a pseudo-twofold axis of symmetry. In both structures, the aliphatic chain fragments are disordered and the disorder persists at lower temperatures.
Supporting information
CCDC references: 735137; 735138; 735139; 735140
The details of the synthesis of and the spectroscopic data for the title
compounds will be published in a separate paper (Koenig et al., 2009).
Crystals appropriate for an X-ray diffraction experiment were obtained by slow
evaporation from heptane solutions.
H atoms were located geometrically and refined as riding with Uiso(H)
= xUeq(C), where x = 1.5 [1.3 for some (e.g. C27) according
to data in CIF?; please check] for methyl H atoms and x = 1.2 for
all others. The representation of the disorder in the alkyl chains by two sets
of atomic positions is probably modelling a larger number of chain
orientations; the disorder components were subjected to weak geometrical
restraints [the C—C bonds were restrained to the target value of 1.54 (2) Å]. In (I), restraints for approximate isotropic behaviour and rigid-bond
restraints were also applied to the displacement parameters. Site occupation
factors were set, on the basis of equivalent displacement parameters, at the
values 0.7/0.3 and 0.5/0.5 in two molecules of (I), while in the case of (II)
the occupancies refined to 0.631 (13)/0.369 (13). Our attempts to refine these
factors in the structure of (I) were abandoned due to high correlations with
the Uij parameters of the disordered fragment. Details of the ambient
temperature structure determinations of compounds (I) and II are deposited as
supplementary data in CIF format.
Data collection: CrysAlis PRO (Oxford Diffraction, 2009) for (I), (II); CrysAlis CCD (Oxford Diffraction, 2007) for Irt, IIrt. Cell refinement: CrysAlis PRO (Oxford Diffraction, 2009) for (I), (II); CrysAlis RED (Oxford Diffraction, 2007) for Irt, IIrt. Data reduction: CrysAlis PRO (Oxford Diffraction, 2009) for (I), (II); CrysAlis RED (Oxford Diffraction, 2007) for Irt, IIrt. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008). Molecular graphics: XP (Siemens, 1989) and Mercury (Macrae et al., 2006) for (I); XP (Siemens, 1989) for (II); XP (Siemens, 1989) Mercury (Macrae et al., 2006) for Irt, IIrt. Software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) for (I), (II).
(I) 3
β,7
α,11
β-triacetoxycucurbit-5(10)-ene
top
Crystal data top
C36H58O6 | F(000) = 2576 |
Mr = 586.82 | Dx = 1.078 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 9774 reflections |
a = 14.0270 (8) Å | θ = 4–22° |
b = 19.6354 (10) Å | µ = 0.07 mm−1 |
c = 26.2445 (12) Å | T = 100 K |
V = 7228.4 (6) Å3 | Block, colourless |
Z = 8 | 0.5 × 0.2 × 0.2 mm |
Data collection top
Kuma KM-4 CCD four-circle diffractometer | 4921 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 25.5°, θmin = 2.1° |
/w scans | h = −14→16 |
33755 measured reflections | k = −23→10 |
7355 independent reflections | l = −31→31 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0943P)2 + 0.5619P] where P = (Fo2 + 2Fc2)/3 |
7355 reflections | (Δ/σ)max < 0.001 |
838 parameters | Δρmax = 0.34 e Å−3 |
164 restraints | Δρmin = −0.21 e Å−3 |
Crystal data top
C36H58O6 | V = 7228.4 (6) Å3 |
Mr = 586.82 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 14.0270 (8) Å | µ = 0.07 mm−1 |
b = 19.6354 (10) Å | T = 100 K |
c = 26.2445 (12) Å | 0.5 × 0.2 × 0.2 mm |
Data collection top
Kuma KM-4 CCD four-circle diffractometer | 4921 reflections with I > 2σ(I) |
33755 measured reflections | Rint = 0.045 |
7355 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.052 | 164 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.34 e Å−3 |
7355 reflections | Δρmin = −0.21 e Å−3 |
838 parameters | |
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 | Occ. (<1) |
C1A | 0.1972 (3) | 1.0198 (2) | 0.83821 (14) | 0.0269 (9) | |
H1A1 | 0.1355 | 1.0217 | 0.8565 | 0.032* | |
H1A2 | 0.1920 | 0.9838 | 0.8119 | 0.032* | |
C2A | 0.2135 (3) | 1.0883 (2) | 0.81155 (15) | 0.0357 (11) | |
H2A1 | 0.2610 | 1.0829 | 0.7840 | 0.043* | |
H2A2 | 0.1531 | 1.1045 | 0.7962 | 0.043* | |
C3A | 0.2488 (3) | 1.1396 (2) | 0.84985 (14) | 0.0271 (10) | |
H3A | 0.2006 | 1.1441 | 0.8777 | 0.033* | |
O31A | 0.2587 (2) | 1.20486 (14) | 0.82442 (10) | 0.0333 (7) | |
C32A | 0.2072 (3) | 1.2578 (2) | 0.84042 (15) | 0.0322 (10) | |
O33A | 0.1524 (2) | 1.25532 (15) | 0.87570 (11) | 0.0441 (8) | |
C34A | 0.2256 (4) | 1.3194 (2) | 0.80875 (18) | 0.0496 (13) | |
H34A | 0.1912 | 1.3575 | 0.8226 | 0.064* | |
H34B | 0.2924 | 1.3294 | 0.8089 | 0.064* | |
H34C | 0.2050 | 1.3113 | 0.7745 | 0.064* | |
C4A | 0.3453 (3) | 1.11979 (19) | 0.87336 (14) | 0.0244 (9) | |
C5A | 0.3396 (3) | 1.0452 (2) | 0.89230 (14) | 0.0233 (9) | |
C6A | 0.4159 (3) | 1.0273 (2) | 0.93040 (15) | 0.0258 (9) | |
H6A | 0.4026 | 1.0517 | 0.9626 | 0.031* | |
H6B | 0.4780 | 1.0437 | 0.9174 | 0.031* | |
C7A | 0.4239 (3) | 0.9510 (2) | 0.94183 (14) | 0.0234 (9) | |
H7A | 0.4664 | 0.9303 | 0.9155 | 0.028* | |
O71A | 0.47322 (18) | 0.94703 (13) | 0.99096 (10) | 0.0256 (6) | |
C72A | 0.5275 (3) | 0.8908 (2) | 0.99910 (17) | 0.0297 (10) | |
O73A | 0.5383 (2) | 0.84663 (14) | 0.96818 (12) | 0.0375 (8) | |
C74A | 0.5706 (3) | 0.8915 (2) | 1.05093 (17) | 0.0403 (11) | |
H74A | 0.6369 | 0.8802 | 1.0487 | 0.052* | |
H74B | 0.5637 | 0.9363 | 1.0652 | 0.052* | |
H74C | 0.5389 | 0.8589 | 1.0722 | 0.052* | |
C8A | 0.3306 (3) | 0.91043 (19) | 0.94241 (13) | 0.0206 (8) | |
H8A | 0.3499 | 0.8614 | 0.9422 | 0.025* | |
C9A | 0.2812 (3) | 0.92324 (19) | 0.88973 (14) | 0.0232 (9) | |
C10A | 0.2745 (3) | 0.9994 (2) | 0.87584 (13) | 0.0225 (9) | |
C11A | 0.1803 (3) | 0.88894 (18) | 0.88740 (14) | 0.0209 (8) | |
H11A | 0.1419 | 0.9128 | 0.8607 | 0.025* | |
O111 | 0.19209 (19) | 0.81728 (13) | 0.87180 (9) | 0.0259 (6) | |
C112 | 0.1533 (3) | 0.7982 (2) | 0.82720 (16) | 0.0338 (10) | |
O113 | 0.1135 (3) | 0.83660 (17) | 0.79835 (11) | 0.0518 (9) | |
C114 | 0.1701 (4) | 0.7237 (2) | 0.8177 (2) | 0.0491 (13) | |
H11B | 0.2363 | 0.7159 | 0.8111 | 0.064* | |
H11C | 0.1510 | 0.6980 | 0.8470 | 0.064* | |
H11D | 0.1334 | 0.7095 | 0.7887 | 0.064* | |
C12A | 0.1218 (3) | 0.8875 (2) | 0.93667 (12) | 0.0203 (8) | |
H12A | 0.0942 | 0.9333 | 0.9425 | 0.024* | |
H12B | 0.0682 | 0.8552 | 0.9323 | 0.024* | |
C13A | 0.1786 (3) | 0.86699 (18) | 0.98344 (14) | 0.0205 (8) | |
C14A | 0.2643 (3) | 0.91870 (19) | 0.98886 (14) | 0.0203 (8) | |
C15A | 0.3043 (3) | 0.8971 (2) | 1.04104 (13) | 0.0236 (9) | |
H15A | 0.3413 | 0.9346 | 1.0567 | 0.028* | |
H15B | 0.3461 | 0.8567 | 1.0376 | 0.028* | |
C16A | 0.2143 (3) | 0.8800 (2) | 1.07367 (14) | 0.0246 (9) | |
H16A | 0.2239 | 0.8367 | 1.0922 | 0.029* | |
H16B | 0.2025 | 0.9166 | 1.0989 | 0.029* | |
C17A | 0.1291 (3) | 0.87382 (19) | 1.03682 (13) | 0.0221 (9) | |
H17A | 0.0946 | 0.9184 | 1.0373 | 0.027* | |
C18A | 0.2122 (3) | 0.79175 (18) | 0.97911 (14) | 0.0217 (8) | |
H18A | 0.2535 | 0.7872 | 0.9502 | 0.028* | |
H18B | 0.2461 | 0.7793 | 1.0094 | 0.028* | |
H18C | 0.1583 | 0.7623 | 0.9750 | 0.028* | |
C19A | 0.3432 (3) | 0.8915 (2) | 0.84656 (14) | 0.0283 (9) | |
H191 | 0.3997 | 0.9183 | 0.8421 | 0.037* | |
H192 | 0.3604 | 0.8456 | 0.8555 | 0.037* | |
H193 | 0.3075 | 0.8911 | 0.8154 | 0.037* | |
C20A | −0.0271 (3) | 0.8114 (2) | 1.01751 (15) | 0.0304 (10) | |
H20A | −0.0066 | 0.7901 | 0.9867 | 0.039* | |
H20B | −0.0749 | 0.7840 | 1.0336 | 0.039* | |
H20C | −0.0528 | 0.8557 | 1.0101 | 0.039* | |
C21A | 0.0575 (3) | 0.8183 (2) | 1.05344 (14) | 0.0251 (9) | |
H21A | 0.0921 | 0.7738 | 1.0533 | 0.030* | |
C22A | 0.0230 (3) | 0.8312 (2) | 1.10836 (15) | 0.0334 (10) | |
H22A | −0.0150 | 0.7915 | 1.1195 | 0.040* | 0.70 |
H22B | 0.0796 | 0.8340 | 1.1309 | 0.040* | 0.70 |
H22C | 0.0809 | 0.8454 | 1.1273 | 0.040* | 0.30 |
H22D | −0.0175 | 0.8724 | 1.1062 | 0.040* | 0.30 |
C23A | −0.0353 (4) | 0.8943 (3) | 1.11644 (18) | 0.0227 (12) | 0.70 |
H23A | 0.0023 | 0.9339 | 1.1073 | 0.027* | 0.70 |
H23B | −0.0898 | 0.8928 | 1.0938 | 0.027* | 0.70 |
C24A | −0.0702 (5) | 0.9006 (3) | 1.1713 (2) | 0.0360 (16) | 0.70 |
H24A | −0.1106 | 0.8618 | 1.1796 | 0.043* | 0.70 |
H24B | −0.0156 | 0.8986 | 1.1939 | 0.043* | 0.70 |
C25A | −0.1267 (6) | 0.9673 (3) | 1.1821 (2) | 0.051 (2) | 0.70 |
H25A | −0.0893 | 1.0067 | 1.1700 | 0.061* | 0.70 |
C26A | −0.2215 (6) | 0.9680 (4) | 1.1561 (3) | 0.061 (2) | 0.70 |
H26A | −0.2564 | 0.9285 | 1.1663 | 0.080* | 0.70 |
H26B | −0.2557 | 1.0085 | 1.1662 | 0.080* | 0.70 |
H26C | −0.2118 | 0.9682 | 1.1204 | 0.080* | 0.70 |
C27A | −0.1436 (8) | 0.9766 (5) | 1.2381 (3) | 0.090 (3) | 0.70 |
H27A | −0.0837 | 0.9838 | 1.2552 | 0.108* | 0.70 |
H27B | −0.1841 | 1.0152 | 1.2444 | 0.108* | 0.70 |
H27C | −0.1726 | 0.9360 | 1.2502 | 0.108* | 0.70 |
C23D | −0.0312 (14) | 0.7826 (8) | 1.1430 (6) | 0.075 (6) | 0.30 |
H23C | 0.0062 | 0.7401 | 1.1469 | 0.090* | 0.30 |
H23D | −0.0926 | 0.7706 | 1.1267 | 0.090* | 0.30 |
C24D | −0.0510 (16) | 0.8130 (10) | 1.1962 (6) | 0.080 (6) | 0.30 |
H24C | 0.0091 | 0.8296 | 1.2116 | 0.096* | 0.30 |
H24D | −0.0957 | 0.8518 | 1.1933 | 0.096* | 0.30 |
C25D | −0.0947 (13) | 0.7566 (9) | 1.2296 (7) | 0.072 (5) | 0.30 |
H25D | −0.1412 | 0.7297 | 1.2089 | 0.087* | 0.30 |
C26D | −0.0157 (13) | 0.7104 (11) | 1.2472 (7) | 0.068 (5) | 0.30 |
H26D | −0.0423 | 0.6740 | 1.2685 | 0.089* | 0.30 |
H26E | 0.0305 | 0.7368 | 1.2672 | 0.089* | 0.30 |
H26F | 0.0163 | 0.6904 | 1.2176 | 0.089* | 0.30 |
C27D | −0.1454 (16) | 0.7870 (11) | 1.2750 (7) | 0.083 (6) | 0.30 |
H27D | −0.1973 | 0.8165 | 1.2632 | 0.108* | 0.30 |
H27E | −0.1001 | 0.8138 | 1.2951 | 0.108* | 0.30 |
H27F | −0.1716 | 0.7503 | 1.2961 | 0.108* | 0.30 |
C28A | 0.4268 (3) | 1.1267 (2) | 0.83493 (17) | 0.0414 (12) | |
H281 | 0.4310 | 1.1730 | 0.8233 | 0.054* | |
H282 | 0.4854 | 1.1140 | 0.8511 | 0.054* | |
H283 | 0.4152 | 1.0971 | 0.8065 | 0.054* | |
C29A | 0.3647 (3) | 1.1689 (2) | 0.91775 (15) | 0.0330 (10) | |
H291 | 0.3206 | 1.1599 | 0.9448 | 0.043* | |
H292 | 0.4284 | 1.1624 | 0.9299 | 0.043* | |
H293 | 0.3572 | 1.2151 | 0.9063 | 0.043* | |
C30A | 0.2283 (3) | 0.99341 (19) | 0.99544 (14) | 0.0232 (9) | |
H30A | 0.2817 | 1.0231 | 1.0005 | 0.030* | |
H30B | 0.1945 | 1.0070 | 0.9654 | 0.030* | |
H30C | 0.1867 | 0.9963 | 1.0243 | 0.030* | |
C1B | 0.9132 (3) | 0.9832 (2) | 0.83354 (14) | 0.0273 (9) | |
H1B1 | 0.9129 | 1.0198 | 0.8076 | 0.033* | |
H1B2 | 0.9780 | 0.9812 | 0.8484 | 0.033* | |
C2B | 0.8921 (3) | 0.9158 (2) | 0.80741 (14) | 0.0292 (10) | |
H2B1 | 0.8369 | 0.9209 | 0.7842 | 0.035* | |
H2B2 | 0.9479 | 0.9012 | 0.7871 | 0.035* | |
C3B | 0.8705 (3) | 0.8641 (2) | 0.84745 (14) | 0.0260 (9) | |
H3B | 0.9246 | 0.8624 | 0.8722 | 0.031* | |
O31B | 0.85996 (19) | 0.79733 (14) | 0.82337 (10) | 0.0294 (7) | |
C32B | 0.9100 (3) | 0.7436 (2) | 0.84289 (16) | 0.0318 (10) | |
O33B | 0.9642 (2) | 0.74746 (15) | 0.87786 (11) | 0.0411 (8) | |
C34B | 0.8860 (3) | 0.6796 (2) | 0.81429 (17) | 0.0401 (11) | |
H34D | 0.9017 | 0.6410 | 0.8351 | 0.052* | |
H34E | 0.8195 | 0.6784 | 0.8061 | 0.052* | |
H34F | 0.9226 | 0.6781 | 0.7835 | 0.052* | |
C4B | 0.7777 (3) | 0.88045 (19) | 0.87649 (14) | 0.0232 (9) | |
C5B | 0.7820 (3) | 0.95562 (19) | 0.89378 (14) | 0.0220 (9) | |
C6B | 0.7098 (3) | 0.9721 (2) | 0.93494 (15) | 0.0273 (9) | |
H6C | 0.7283 | 0.9481 | 0.9666 | 0.033* | |
H6D | 0.6468 | 0.9544 | 0.9243 | 0.033* | |
C7B | 0.7000 (3) | 1.0477 (2) | 0.94660 (14) | 0.0254 (9) | |
H7B | 0.6551 | 1.0676 | 0.9211 | 0.031* | |
O71B | 0.65418 (18) | 1.05103 (13) | 0.99640 (10) | 0.0278 (6) | |
C72B | 0.5977 (3) | 1.1055 (2) | 1.00499 (18) | 0.0329 (10) | |
O73B | 0.5841 (2) | 1.14949 (15) | 0.97433 (13) | 0.0424 (8) | |
C74B | 0.5547 (3) | 1.1025 (2) | 1.05696 (19) | 0.0476 (13) | |
H74D | 0.4874 | 1.1097 | 1.0543 | 0.062* | |
H74E | 0.5666 | 1.0586 | 1.0719 | 0.062* | |
H74F | 0.5821 | 1.1374 | 1.0780 | 0.062* | |
C8B | 0.7921 (3) | 1.08913 (19) | 0.94494 (13) | 0.0194 (8) | |
H8B | 0.7713 | 1.1378 | 0.9456 | 0.023* | |
C9B | 0.8382 (3) | 1.07824 (19) | 0.89057 (14) | 0.0218 (9) | |
C10B | 0.8429 (3) | 1.0016 (2) | 0.87538 (13) | 0.0209 (8) | |
C11B | 0.9389 (3) | 1.11303 (19) | 0.88679 (14) | 0.0243 (9) | |
H11E | 0.9752 | 1.0895 | 0.8591 | 0.029* | |
O115 | 0.92733 (19) | 1.18420 (13) | 0.87167 (9) | 0.0282 (6) | |
C116 | 0.9580 (3) | 1.2034 (3) | 0.82553 (17) | 0.0409 (12) | |
O117 | 0.9892 (3) | 1.1643 (2) | 0.79414 (12) | 0.0597 (11) | |
C118 | 0.9459 (4) | 1.2780 (3) | 0.8186 (2) | 0.0629 (17) | |
H11F | 0.9697 | 1.2919 | 0.7859 | 0.082* | |
H11G | 0.8795 | 1.2887 | 0.8208 | 0.082* | |
H11H | 0.9798 | 1.3017 | 0.8449 | 0.082* | |
C12B | 1.0012 (3) | 1.11297 (19) | 0.93439 (13) | 0.0206 (8) | |
H12C | 1.0277 | 1.0667 | 0.9394 | 0.025* | |
H12D | 1.0553 | 1.1446 | 0.9291 | 0.025* | |
C13B | 0.9475 (3) | 1.13397 (18) | 0.98236 (13) | 0.0193 (8) | |
C14B | 0.8630 (3) | 1.08168 (19) | 0.98991 (13) | 0.0199 (8) | |
C15B | 0.8264 (3) | 1.1036 (2) | 1.04280 (13) | 0.0265 (9) | |
H15C | 0.7908 | 1.0661 | 1.0594 | 0.032* | |
H15D | 0.7842 | 1.1438 | 1.0400 | 0.032* | |
C16B | 0.9179 (3) | 1.1211 (2) | 1.07319 (14) | 0.0294 (10) | |
H16C | 0.9322 | 1.0844 | 1.0979 | 0.035* | |
H16D | 0.9090 | 1.1642 | 1.0922 | 0.035* | |
C17B | 1.0019 (3) | 1.1285 (2) | 1.03403 (14) | 0.0252 (9) | |
H17B | 1.0379 | 1.0845 | 1.0338 | 0.030* | |
C18B | 0.9121 (3) | 1.20848 (18) | 0.97811 (13) | 0.0207 (8) | |
H18D | 0.8649 | 1.2114 | 0.9518 | 0.027* | |
H18E | 0.8849 | 1.2225 | 1.0099 | 0.027* | |
H18F | 0.9646 | 1.2377 | 0.9698 | 0.027* | |
C19B | 0.7731 (3) | 1.1120 (2) | 0.85003 (14) | 0.0317 (10) | |
H194 | 0.7151 | 1.0864 | 0.8473 | 0.041* | |
H195 | 0.7588 | 1.1580 | 0.8600 | 0.041* | |
H196 | 0.8049 | 1.1122 | 0.8177 | 0.041* | |
C20B | 1.1548 (3) | 1.1915 (2) | 1.01173 (15) | 0.0317 (10) | |
H20D | 1.1325 | 1.2103 | 0.9802 | 0.041* | |
H20E | 1.2024 | 1.2209 | 1.0260 | 0.041* | |
H20F | 1.1816 | 1.1472 | 1.0057 | 0.041* | |
C21B | 1.0722 (3) | 1.1851 (2) | 1.04892 (14) | 0.0299 (10) | |
H21B | 1.0362 | 1.2290 | 1.0474 | 0.036* | |
C22B | 1.1100 (4) | 1.1783 (3) | 1.10350 (18) | 0.0521 (14) | |
H22E | 1.1540 | 1.2167 | 1.1101 | 0.063* | |
H22F | 1.0556 | 1.1832 | 1.1272 | 0.063* | |
C23B | 1.1612 (4) | 1.1132 (3) | 1.1161 (2) | 0.0677 (17) | |
H23E | 1.2218 | 1.1099 | 1.0969 | 0.081* | 0.50 |
H23F | 1.1211 | 1.0732 | 1.1077 | 0.081* | 0.50 |
H23G | 1.1877 | 1.0963 | 1.0835 | 0.081* | 0.50 |
H23H | 1.1114 | 1.0802 | 1.1264 | 0.081* | 0.50 |
C24B | 1.1803 (9) | 1.1177 (5) | 1.1752 (3) | 0.052 (3) | 0.50 |
H24E | 1.1199 | 1.1291 | 1.1927 | 0.062* | 0.50 |
H24F | 1.2261 | 1.1551 | 1.1818 | 0.062* | 0.50 |
C25B | 1.2213 (9) | 1.0496 (6) | 1.1984 (4) | 0.061 (3) | 0.50 |
H25B | 1.2367 | 1.0579 | 1.2351 | 0.074* | 0.50 |
C26B | 1.1400 (10) | 0.9933 (7) | 1.1956 (6) | 0.071 (5) | 0.50 |
H26G | 1.1672 | 0.9491 | 1.2015 | 0.093* | 0.50 |
H26H | 1.0934 | 1.0029 | 1.2213 | 0.093* | 0.50 |
H26I | 1.1103 | 0.9940 | 1.1627 | 0.093* | 0.50 |
C27B | 1.3142 (11) | 1.0283 (11) | 1.1707 (8) | 0.069 (6) | 0.50 |
H27G | 1.3015 | 1.0229 | 1.1350 | 0.083* | 0.50 |
H27H | 1.3612 | 1.0632 | 1.1754 | 0.083* | 0.50 |
H27I | 1.3374 | 0.9860 | 1.1843 | 0.083* | 0.50 |
C24C | 1.2393 (8) | 1.1065 (5) | 1.1545 (5) | 0.059 (3) | 0.50 |
H24G | 1.2164 | 1.1269 | 1.1867 | 0.070* | 0.50 |
H24H | 1.2935 | 1.1346 | 1.1426 | 0.070* | 0.50 |
C25C | 1.2788 (11) | 1.0345 (8) | 1.1672 (6) | 0.046 (4) | 0.50 |
H25C | 1.2955 | 1.0107 | 1.1346 | 0.056* | 0.50 |
C26C | 1.3686 (10) | 1.0408 (7) | 1.1999 (5) | 0.081 (4) | 0.50 |
H26J | 1.3816 | 0.9982 | 1.2165 | 0.105* | 0.50 |
H26K | 1.4214 | 1.0529 | 1.1786 | 0.105* | 0.50 |
H26L | 1.3589 | 1.0756 | 1.2250 | 0.105* | 0.50 |
C27C | 1.1993 (9) | 0.9938 (6) | 1.1947 (4) | 0.046 (3) | 0.50 |
H27J | 1.1822 | 1.0170 | 1.2255 | 0.055* | 0.50 |
H27K | 1.1443 | 0.9895 | 1.1733 | 0.055* | 0.50 |
H27L | 1.2233 | 0.9492 | 1.2028 | 0.055* | 0.50 |
C28B | 0.6892 (3) | 0.8704 (2) | 0.84234 (15) | 0.0307 (10) | |
H284 | 0.6326 | 0.8788 | 0.8618 | 0.040* | |
H285 | 0.6921 | 0.9018 | 0.8143 | 0.040* | |
H286 | 0.6881 | 0.8245 | 0.8296 | 0.040* | |
C29B | 0.7691 (3) | 0.8318 (2) | 0.92209 (14) | 0.0273 (9) | |
H294 | 0.8208 | 0.8396 | 0.9452 | 0.036* | |
H295 | 0.7100 | 0.8400 | 0.9393 | 0.036* | |
H296 | 0.7710 | 0.7855 | 0.9103 | 0.036* | |
C30B | 0.8992 (3) | 1.00858 (19) | 0.99610 (14) | 0.0248 (9) | |
H30D | 0.8474 | 0.9793 | 1.0054 | 0.032* | |
H30E | 0.9261 | 0.9934 | 0.9645 | 0.032* | |
H30F | 0.9469 | 1.0072 | 1.0222 | 0.032* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.032 (2) | 0.028 (2) | 0.0200 (19) | −0.0042 (19) | −0.0031 (17) | 0.0001 (17) |
C2A | 0.042 (3) | 0.037 (3) | 0.028 (2) | −0.003 (2) | −0.004 (2) | 0.006 (2) |
C3A | 0.035 (2) | 0.024 (2) | 0.0215 (19) | −0.001 (2) | 0.0074 (18) | 0.0042 (18) |
O31A | 0.0453 (18) | 0.0257 (16) | 0.0289 (14) | 0.0016 (15) | 0.0045 (14) | 0.0096 (14) |
C32A | 0.044 (3) | 0.031 (3) | 0.021 (2) | 0.002 (2) | −0.003 (2) | 0.0046 (19) |
O33A | 0.063 (2) | 0.0292 (17) | 0.0398 (18) | 0.0119 (16) | 0.0009 (18) | 0.0031 (15) |
C34A | 0.070 (3) | 0.026 (2) | 0.052 (3) | −0.002 (3) | −0.006 (3) | 0.009 (2) |
C4A | 0.029 (2) | 0.019 (2) | 0.0254 (19) | −0.0014 (18) | 0.0007 (18) | 0.0009 (17) |
C5A | 0.022 (2) | 0.022 (2) | 0.0267 (19) | 0.0042 (18) | 0.0052 (17) | −0.0005 (18) |
C6A | 0.019 (2) | 0.022 (2) | 0.037 (2) | −0.0046 (17) | −0.0030 (18) | 0.0019 (18) |
C7A | 0.022 (2) | 0.022 (2) | 0.0261 (19) | 0.0037 (18) | −0.0028 (17) | 0.0010 (18) |
O71A | 0.0193 (14) | 0.0208 (14) | 0.0366 (15) | 0.0000 (12) | −0.0041 (12) | −0.0008 (13) |
C72A | 0.017 (2) | 0.020 (2) | 0.052 (3) | 0.0003 (19) | 0.003 (2) | 0.009 (2) |
O73A | 0.0303 (17) | 0.0212 (16) | 0.061 (2) | 0.0066 (14) | 0.0023 (15) | −0.0013 (16) |
C74A | 0.028 (2) | 0.038 (3) | 0.054 (3) | −0.001 (2) | −0.013 (2) | 0.012 (2) |
C8A | 0.023 (2) | 0.0168 (19) | 0.0216 (18) | 0.0001 (17) | −0.0006 (16) | −0.0037 (16) |
C9A | 0.025 (2) | 0.021 (2) | 0.0234 (19) | −0.0002 (18) | −0.0002 (17) | −0.0044 (17) |
C10A | 0.028 (2) | 0.022 (2) | 0.0174 (18) | 0.0018 (19) | 0.0050 (16) | −0.0029 (17) |
C11A | 0.024 (2) | 0.0150 (19) | 0.0235 (19) | 0.0035 (17) | −0.0034 (16) | −0.0048 (16) |
O111 | 0.0314 (16) | 0.0197 (14) | 0.0268 (13) | −0.0008 (13) | −0.0041 (12) | −0.0060 (12) |
C112 | 0.040 (3) | 0.029 (2) | 0.033 (2) | −0.002 (2) | −0.007 (2) | −0.009 (2) |
O113 | 0.072 (2) | 0.046 (2) | 0.0366 (17) | 0.0105 (19) | −0.0259 (17) | −0.0140 (16) |
C114 | 0.050 (3) | 0.037 (3) | 0.060 (3) | −0.002 (2) | −0.005 (3) | −0.023 (2) |
C12A | 0.017 (2) | 0.019 (2) | 0.0245 (19) | 0.0007 (17) | −0.0029 (16) | −0.0038 (17) |
C13A | 0.021 (2) | 0.0151 (19) | 0.0251 (19) | −0.0021 (17) | −0.0015 (16) | −0.0014 (16) |
C14A | 0.018 (2) | 0.0173 (19) | 0.0253 (19) | −0.0014 (17) | −0.0021 (16) | −0.0019 (17) |
C15A | 0.020 (2) | 0.025 (2) | 0.026 (2) | −0.0017 (18) | −0.0061 (16) | −0.0058 (17) |
C16A | 0.023 (2) | 0.025 (2) | 0.0259 (19) | 0.0005 (18) | −0.0020 (17) | −0.0008 (17) |
C17A | 0.023 (2) | 0.021 (2) | 0.0218 (19) | 0.0016 (18) | 0.0001 (16) | −0.0019 (17) |
C18A | 0.022 (2) | 0.018 (2) | 0.0257 (19) | 0.0003 (17) | −0.0011 (17) | −0.0019 (17) |
C19A | 0.032 (2) | 0.025 (2) | 0.028 (2) | −0.001 (2) | 0.0033 (18) | −0.0097 (18) |
C20A | 0.018 (2) | 0.034 (2) | 0.040 (2) | −0.0041 (19) | 0.0004 (18) | 0.002 (2) |
C21A | 0.022 (2) | 0.021 (2) | 0.033 (2) | −0.0024 (18) | 0.0014 (18) | 0.0051 (18) |
C22A | 0.029 (2) | 0.039 (3) | 0.032 (2) | 0.000 (2) | 0.0034 (19) | 0.007 (2) |
C23A | 0.031 (3) | 0.021 (3) | 0.017 (2) | 0.005 (3) | 0.013 (2) | 0.005 (2) |
C24A | 0.049 (4) | 0.032 (3) | 0.027 (3) | 0.012 (3) | 0.024 (3) | 0.005 (3) |
C25A | 0.084 (6) | 0.034 (4) | 0.034 (3) | 0.011 (4) | 0.030 (4) | 0.006 (3) |
C26A | 0.063 (5) | 0.036 (4) | 0.085 (5) | 0.028 (4) | 0.033 (4) | 0.022 (4) |
C27A | 0.140 (9) | 0.074 (6) | 0.056 (5) | 0.026 (6) | 0.051 (5) | −0.017 (4) |
C23D | 0.085 (13) | 0.068 (11) | 0.072 (10) | −0.004 (10) | 0.007 (9) | 0.011 (9) |
C24D | 0.085 (13) | 0.089 (12) | 0.066 (9) | 0.000 (11) | 0.016 (9) | 0.009 (9) |
C25D | 0.072 (11) | 0.065 (11) | 0.081 (11) | −0.019 (9) | 0.012 (9) | 0.000 (9) |
C26D | 0.049 (10) | 0.114 (13) | 0.042 (8) | 0.020 (10) | −0.002 (8) | −0.002 (9) |
C27D | 0.086 (13) | 0.090 (13) | 0.072 (11) | 0.000 (11) | 0.010 (10) | 0.013 (10) |
C28A | 0.038 (3) | 0.040 (3) | 0.047 (3) | −0.001 (2) | 0.012 (2) | 0.009 (2) |
C29A | 0.036 (3) | 0.020 (2) | 0.043 (2) | −0.001 (2) | −0.008 (2) | −0.0039 (19) |
C30A | 0.022 (2) | 0.022 (2) | 0.0255 (19) | −0.0017 (18) | −0.0015 (17) | −0.0057 (17) |
C1B | 0.029 (2) | 0.032 (2) | 0.0215 (19) | −0.0014 (19) | 0.0009 (17) | −0.0049 (18) |
C2B | 0.033 (2) | 0.030 (2) | 0.025 (2) | −0.009 (2) | 0.0028 (18) | −0.0062 (18) |
C3B | 0.026 (2) | 0.025 (2) | 0.028 (2) | −0.0037 (19) | −0.0022 (18) | −0.0138 (18) |
O31B | 0.0317 (16) | 0.0269 (16) | 0.0297 (14) | −0.0025 (14) | 0.0008 (13) | −0.0113 (13) |
C32B | 0.037 (3) | 0.026 (2) | 0.032 (2) | −0.001 (2) | 0.012 (2) | −0.001 (2) |
O33B | 0.048 (2) | 0.0343 (18) | 0.0408 (17) | 0.0042 (16) | −0.0094 (16) | −0.0025 (15) |
C34B | 0.049 (3) | 0.029 (2) | 0.042 (2) | −0.003 (2) | 0.013 (2) | −0.011 (2) |
C4B | 0.023 (2) | 0.021 (2) | 0.0256 (19) | −0.0048 (18) | −0.0053 (17) | −0.0061 (17) |
C5B | 0.020 (2) | 0.020 (2) | 0.0266 (19) | 0.0003 (18) | −0.0030 (17) | −0.0034 (18) |
C6B | 0.025 (2) | 0.026 (2) | 0.030 (2) | −0.0012 (18) | 0.0040 (18) | −0.0013 (18) |
C7B | 0.021 (2) | 0.024 (2) | 0.031 (2) | −0.0036 (18) | 0.0036 (17) | 0.0018 (19) |
O71B | 0.0238 (15) | 0.0195 (14) | 0.0400 (16) | −0.0013 (13) | 0.0119 (13) | −0.0055 (13) |
C72B | 0.022 (2) | 0.024 (2) | 0.053 (3) | −0.006 (2) | 0.003 (2) | −0.010 (2) |
O73B | 0.0305 (18) | 0.0281 (17) | 0.069 (2) | 0.0066 (15) | −0.0031 (16) | −0.0102 (17) |
C74B | 0.035 (3) | 0.034 (3) | 0.074 (3) | −0.003 (2) | 0.024 (3) | −0.021 (3) |
C8B | 0.019 (2) | 0.0133 (19) | 0.0258 (19) | 0.0010 (16) | 0.0020 (17) | −0.0005 (16) |
C9B | 0.021 (2) | 0.022 (2) | 0.0221 (19) | −0.0038 (18) | −0.0007 (17) | −0.0007 (17) |
C10B | 0.020 (2) | 0.025 (2) | 0.0182 (18) | −0.0054 (18) | −0.0036 (15) | 0.0002 (17) |
C11B | 0.030 (2) | 0.022 (2) | 0.0209 (18) | −0.0067 (19) | 0.0072 (17) | −0.0016 (17) |
O115 | 0.0382 (17) | 0.0259 (15) | 0.0206 (13) | −0.0078 (14) | −0.0015 (12) | 0.0049 (12) |
C116 | 0.031 (3) | 0.061 (3) | 0.030 (2) | −0.016 (3) | −0.010 (2) | 0.018 (3) |
O117 | 0.062 (2) | 0.092 (3) | 0.0251 (16) | −0.014 (2) | 0.0093 (17) | 0.0155 (19) |
C118 | 0.060 (4) | 0.066 (4) | 0.063 (3) | −0.027 (3) | −0.020 (3) | 0.044 (3) |
C12B | 0.017 (2) | 0.019 (2) | 0.0256 (19) | −0.0011 (17) | 0.0014 (16) | −0.0024 (17) |
C13B | 0.020 (2) | 0.0161 (19) | 0.0218 (18) | 0.0015 (17) | −0.0019 (16) | 0.0012 (16) |
C14B | 0.019 (2) | 0.0187 (19) | 0.0218 (18) | 0.0001 (17) | 0.0013 (16) | 0.0014 (16) |
C15B | 0.028 (2) | 0.027 (2) | 0.025 (2) | 0.0024 (19) | 0.0007 (17) | −0.0010 (18) |
C16B | 0.031 (2) | 0.033 (2) | 0.024 (2) | 0.003 (2) | −0.0008 (18) | −0.0003 (18) |
C17B | 0.024 (2) | 0.026 (2) | 0.0261 (19) | 0.0042 (19) | −0.0005 (17) | 0.0053 (17) |
C18B | 0.019 (2) | 0.020 (2) | 0.0229 (18) | 0.0003 (17) | 0.0020 (16) | −0.0007 (17) |
C19B | 0.029 (2) | 0.037 (3) | 0.029 (2) | −0.005 (2) | −0.0038 (19) | 0.002 (2) |
C20B | 0.025 (2) | 0.032 (2) | 0.038 (2) | −0.001 (2) | −0.0074 (19) | −0.005 (2) |
C21B | 0.027 (2) | 0.032 (2) | 0.031 (2) | 0.006 (2) | −0.0098 (19) | −0.0030 (19) |
C22B | 0.052 (3) | 0.058 (3) | 0.047 (3) | −0.016 (3) | −0.017 (3) | 0.006 (3) |
C23B | 0.079 (4) | 0.053 (3) | 0.071 (4) | −0.020 (3) | −0.037 (3) | 0.019 (3) |
C24B | 0.046 (6) | 0.053 (6) | 0.056 (6) | 0.027 (6) | −0.016 (5) | −0.016 (5) |
C25B | 0.103 (9) | 0.056 (7) | 0.024 (5) | 0.025 (7) | −0.022 (6) | −0.012 (5) |
C26B | 0.070 (9) | 0.074 (9) | 0.070 (8) | 0.020 (9) | −0.013 (8) | 0.025 (7) |
C27B | 0.067 (11) | 0.058 (9) | 0.083 (11) | 0.018 (8) | −0.053 (9) | −0.017 (7) |
C24C | 0.049 (7) | 0.047 (7) | 0.080 (7) | −0.001 (6) | −0.011 (6) | −0.003 (6) |
C25C | 0.057 (10) | 0.046 (8) | 0.036 (6) | −0.005 (8) | −0.021 (8) | 0.005 (6) |
C26C | 0.099 (10) | 0.085 (9) | 0.058 (7) | 0.004 (8) | −0.017 (7) | 0.009 (7) |
C27C | 0.081 (9) | 0.038 (7) | 0.019 (4) | 0.015 (7) | −0.022 (6) | −0.005 (4) |
C28B | 0.028 (2) | 0.027 (2) | 0.037 (2) | −0.004 (2) | −0.0083 (19) | −0.0033 (19) |
C29B | 0.030 (2) | 0.022 (2) | 0.030 (2) | 0.0032 (19) | −0.0001 (18) | −0.0028 (18) |
C30B | 0.024 (2) | 0.022 (2) | 0.029 (2) | 0.0014 (18) | 0.0000 (18) | 0.0036 (18) |
Geometric parameters (Å, º) top
C1A—C10A | 1.520 (5) | C30A—H30C | 0.9579 |
C1A—C2A | 1.534 (5) | C1B—C2B | 1.519 (5) |
C1A—H1A1 | 0.9900 | C1B—C10B | 1.519 (5) |
C1A—H1A2 | 0.9900 | C1B—H1B1 | 0.9900 |
C2A—C3A | 1.507 (6) | C1B—H1B2 | 0.9900 |
C2A—H2A1 | 0.9900 | C2B—C3B | 1.492 (5) |
C2A—H2A2 | 0.9900 | C2B—H2B1 | 0.9900 |
C3A—O31A | 1.451 (4) | C2B—H2B2 | 0.9900 |
C3A—C4A | 1.537 (6) | C3B—O31B | 1.463 (4) |
C3A—H3A | 1.0000 | C3B—C4B | 1.542 (5) |
O31A—C32A | 1.333 (5) | C3B—H3B | 1.0000 |
C32A—O33A | 1.205 (5) | O31B—C32B | 1.367 (5) |
C32A—C34A | 1.490 (6) | C32B—O33B | 1.194 (5) |
C34A—H34A | 0.9600 | C32B—C34B | 1.502 (6) |
C34A—H34B | 0.9570 | C34B—H34D | 0.9604 |
C34A—H34C | 0.9586 | C34B—H34E | 0.9570 |
C4A—C28A | 1.531 (6) | C34B—H34F | 0.9580 |
C4A—C29A | 1.537 (5) | C4B—C29B | 1.536 (5) |
C4A—C5A | 1.549 (5) | C4B—C28B | 1.544 (5) |
C5A—C10A | 1.352 (5) | C4B—C5B | 1.545 (5) |
C5A—C6A | 1.506 (5) | C5B—C10B | 1.334 (5) |
C6A—C7A | 1.531 (5) | C5B—C6B | 1.517 (5) |
C6A—H6A | 0.9900 | C6B—C7B | 1.520 (5) |
C6A—H6B | 0.9900 | C6B—H6C | 0.9900 |
C7A—O71A | 1.466 (4) | C6B—H6D | 0.9900 |
C7A—C8A | 1.532 (5) | C7B—O71B | 1.458 (4) |
C7A—H7A | 1.0000 | C7B—C8B | 1.527 (5) |
O71A—C72A | 1.359 (5) | C7B—H7B | 1.0000 |
C72A—O73A | 1.197 (5) | O71B—C72B | 1.350 (5) |
C72A—C74A | 1.489 (6) | C72B—O73B | 1.196 (5) |
C74A—H74A | 0.9573 | C72B—C74B | 1.492 (6) |
C74A—H74B | 0.9609 | C74B—H74D | 0.9569 |
C74A—H74C | 0.9594 | C74B—H74E | 0.9609 |
C8A—C14A | 1.542 (5) | C74B—H74F | 0.9597 |
C8A—C9A | 1.567 (5) | C8B—C14B | 1.550 (5) |
C8A—H8A | 1.0000 | C8B—C9B | 1.581 (5) |
C9A—C10A | 1.542 (5) | C8B—H8B | 1.0000 |
C9A—C19A | 1.559 (5) | C9B—C19B | 1.551 (5) |
C9A—C11A | 1.568 (5) | C9B—C10B | 1.558 (5) |
C11A—O111 | 1.475 (4) | C9B—C11B | 1.573 (5) |
C11A—C12A | 1.532 (5) | C11B—O115 | 1.462 (4) |
C11A—H11A | 1.0000 | C11B—C12B | 1.524 (5) |
O111—C112 | 1.344 (5) | C11B—H11E | 1.0000 |
C112—O113 | 1.205 (5) | O115—C116 | 1.339 (5) |
C112—C114 | 1.503 (6) | C116—O117 | 1.208 (6) |
C114—H11B | 0.9572 | C116—C118 | 1.486 (7) |
C114—H11C | 0.9593 | C118—H11F | 0.9589 |
C114—H11D | 0.9585 | C118—H11G | 0.9571 |
C12A—C13A | 1.518 (5) | C118—H11H | 0.9588 |
C12A—H12A | 0.9900 | C12B—C13B | 1.524 (5) |
C12A—H12B | 0.9900 | C12B—H12C | 0.9900 |
C13A—C18A | 1.555 (5) | C12B—H12D | 0.9900 |
C13A—C17A | 1.569 (5) | C13B—C18B | 1.549 (5) |
C13A—C14A | 1.579 (5) | C13B—C17B | 1.560 (5) |
C14A—C15A | 1.540 (5) | C13B—C14B | 1.580 (5) |
C14A—C30A | 1.561 (5) | C14B—C30B | 1.531 (5) |
C15A—C16A | 1.562 (5) | C14B—C15B | 1.541 (5) |
C15A—H15A | 0.9900 | C15B—C16B | 1.549 (6) |
C15A—H15B | 0.9900 | C15B—H15C | 0.9900 |
C16A—C17A | 1.542 (5) | C15B—H15D | 0.9900 |
C16A—H16A | 0.9900 | C16B—C17B | 1.570 (5) |
C16A—H16B | 0.9900 | C16B—H16C | 0.9900 |
C17A—C21A | 1.546 (5) | C16B—H16D | 0.9900 |
C17A—H17A | 1.0000 | C17B—C21B | 1.537 (6) |
C18A—H18A | 0.9581 | C17B—H17B | 1.0000 |
C18A—H18B | 0.9584 | C18B—H18D | 0.9577 |
C18A—H18C | 0.9585 | C18B—H18E | 0.9588 |
C19A—H191 | 0.9583 | C18B—H18F | 0.9584 |
C19A—H192 | 0.9610 | C19B—H194 | 0.9581 |
C19A—H193 | 0.9583 | C19B—H195 | 0.9611 |
C20A—C21A | 1.522 (5) | C19B—H196 | 0.9584 |
C20A—H20A | 0.9546 | C20B—C21B | 1.519 (6) |
C20A—H20B | 0.9577 | C20B—H20D | 0.9587 |
C20A—H20C | 0.9619 | C20B—H20E | 0.9588 |
C21A—C22A | 1.541 (5) | C20B—H20F | 0.9608 |
C21A—H21A | 1.0000 | C21B—C22B | 1.533 (6) |
C22A—C23A | 1.500 (6) | C21B—H21B | 1.0000 |
C22A—C23D | 1.521 (6) | C22B—C23B | 1.504 (7) |
C22A—H22A | 0.9881 | C22B—H22E | 0.9900 |
C22A—H22B | 0.9916 | C22B—H22F | 0.9900 |
C22A—H22C | 0.9920 | C23B—C24C | 1.493 (10) |
C22A—H22D | 0.9917 | C23B—C24B | 1.575 (6) |
C23A—C24A | 1.525 (6) | C23B—H23E | 0.9900 |
C23A—H23A | 0.9712 | C23B—H23F | 0.9900 |
C23A—H23B | 0.9685 | C23B—H23G | 0.9900 |
C24A—C25A | 1.557 (8) | C23B—H23H | 0.9900 |
C24A—H24A | 0.9735 | C24B—C25B | 1.578 (12) |
C24A—H24B | 0.9701 | C24B—H24E | 0.9900 |
C25A—C26A | 1.494 (10) | C24B—H24F | 0.9900 |
C25A—C27A | 1.502 (8) | C25B—C27B | 1.550 (16) |
C25A—H25A | 0.9861 | C25B—C26B | 1.589 (15) |
C26A—H26A | 0.9551 | C25B—H25B | 1.0000 |
C26A—H26B | 0.9658 | C26B—H26G | 0.9607 |
C26A—H26C | 0.9486 | C26B—H26H | 0.9579 |
C27A—H27A | 0.9629 | C26B—H26I | 0.9582 |
C27A—H27B | 0.9603 | C27B—H27G | 0.9586 |
C27A—H27C | 0.9493 | C27B—H27H | 0.9593 |
C23D—C24D | 1.544 (17) | C27B—H27I | 0.9605 |
C23D—H23C | 0.9900 | C24C—C25C | 1.554 (15) |
C23D—H23D | 0.9900 | C24C—H24G | 0.9900 |
C24D—C25D | 1.540 (17) | C24C—H24H | 0.9900 |
C24D—H24C | 0.9900 | C25C—C26C | 1.529 (14) |
C24D—H24D | 0.9900 | C25C—C27C | 1.551 (15) |
C25D—C26D | 1.506 (17) | C25C—H25C | 1.0000 |
C25D—C27D | 1.511 (17) | C26C—H26J | 0.9605 |
C25D—H25D | 1.0000 | C26C—H26K | 0.9578 |
C26D—H26D | 0.9800 | C26C—H26L | 0.9600 |
C26D—H26E | 0.9800 | C27C—H27J | 0.9591 |
C26D—H26F | 0.9800 | C27C—H27K | 0.9574 |
C27D—H27D | 0.9800 | C27C—H27L | 0.9608 |
C27D—H27E | 0.9800 | C28B—H284 | 0.9575 |
C27D—H27F | 0.9800 | C28B—H285 | 0.9599 |
C28A—H281 | 0.9612 | C28B—H286 | 0.9610 |
C28A—H282 | 0.9577 | C29B—H294 | 0.9579 |
C28A—H283 | 0.9596 | C29B—H295 | 0.9575 |
C29A—H291 | 0.9580 | C29B—H296 | 0.9610 |
C29A—H292 | 0.9572 | C30B—H30D | 0.9586 |
C29A—H293 | 0.9610 | C30B—H30E | 0.9589 |
C30A—H30A | 0.9585 | C30B—H30F | 0.9576 |
C30A—H30B | 0.9585 | | |
| | | |
C10A—C1A—C2A | 114.9 (3) | H30A—C30A—H30B | 109.3 |
C10A—C1A—H1A1 | 108.5 | C14A—C30A—H30C | 109.9 |
C2A—C1A—H1A1 | 108.5 | H30A—C30A—H30C | 109.4 |
C10A—C1A—H1A2 | 108.5 | H30B—C30A—H30C | 109.5 |
C2A—C1A—H1A2 | 108.5 | C2B—C1B—C10B | 114.1 (3) |
H1A1—C1A—H1A2 | 107.5 | C2B—C1B—H1B1 | 108.7 |
C3A—C2A—C1A | 109.4 (3) | C10B—C1B—H1B1 | 108.7 |
C3A—C2A—H2A1 | 109.8 | C2B—C1B—H1B2 | 108.7 |
C1A—C2A—H2A1 | 109.8 | C10B—C1B—H1B2 | 108.7 |
C3A—C2A—H2A2 | 109.8 | H1B1—C1B—H1B2 | 107.6 |
C1A—C2A—H2A2 | 109.8 | C3B—C2B—C1B | 108.3 (3) |
H2A1—C2A—H2A2 | 108.2 | C3B—C2B—H2B1 | 110.0 |
O31A—C3A—C2A | 108.3 (3) | C1B—C2B—H2B1 | 110.0 |
O31A—C3A—C4A | 109.0 (3) | C3B—C2B—H2B2 | 110.0 |
C2A—C3A—C4A | 112.8 (3) | C1B—C2B—H2B2 | 110.0 |
O31A—C3A—H3A | 108.9 | H2B1—C2B—H2B2 | 108.4 |
C2A—C3A—H3A | 108.9 | O31B—C3B—C2B | 109.0 (3) |
C4A—C3A—H3A | 108.9 | O31B—C3B—C4B | 108.4 (3) |
C32A—O31A—C3A | 119.5 (3) | C2B—C3B—C4B | 112.2 (3) |
O33A—C32A—O31A | 123.8 (4) | O31B—C3B—H3B | 109.1 |
O33A—C32A—C34A | 124.9 (4) | C2B—C3B—H3B | 109.1 |
O31A—C32A—C34A | 111.4 (4) | C4B—C3B—H3B | 109.1 |
C32A—C34A—H34A | 109.5 | C32B—O31B—C3B | 118.6 (3) |
C32A—C34A—H34B | 109.4 | O33B—C32B—O31B | 124.4 (4) |
H34A—C34A—H34B | 109.3 | O33B—C32B—C34B | 125.5 (4) |
C32A—C34A—H34C | 109.7 | O31B—C32B—C34B | 110.1 (4) |
H34A—C34A—H34C | 109.5 | C32B—C34B—H34D | 109.0 |
H34B—C34A—H34C | 109.5 | C32B—C34B—H34E | 110.5 |
C28A—C4A—C29A | 108.1 (3) | H34D—C34B—H34E | 109.4 |
C28A—C4A—C3A | 111.7 (3) | C32B—C34B—H34F | 109.1 |
C29A—C4A—C3A | 107.5 (3) | H34D—C34B—H34F | 109.5 |
C28A—C4A—C5A | 109.5 (3) | H34E—C34B—H34F | 109.4 |
C29A—C4A—C5A | 111.1 (3) | C29B—C4B—C3B | 108.8 (3) |
C3A—C4A—C5A | 108.9 (3) | C29B—C4B—C28B | 108.0 (3) |
C10A—C5A—C6A | 122.5 (4) | C3B—C4B—C28B | 111.4 (3) |
C10A—C5A—C4A | 124.1 (3) | C29B—C4B—C5B | 111.6 (3) |
C6A—C5A—C4A | 113.4 (3) | C3B—C4B—C5B | 108.1 (3) |
C5A—C6A—C7A | 114.2 (3) | C28B—C4B—C5B | 108.9 (3) |
C5A—C6A—H6A | 108.7 | C10B—C5B—C6B | 122.8 (3) |
C7A—C6A—H6A | 108.7 | C10B—C5B—C4B | 124.4 (3) |
C5A—C6A—H6B | 108.7 | C6B—C5B—C4B | 112.8 (3) |
C7A—C6A—H6B | 108.7 | C5B—C6B—C7B | 114.3 (3) |
H6A—C6A—H6B | 107.6 | C5B—C6B—H6C | 108.7 |
O71A—C7A—C6A | 105.0 (3) | C7B—C6B—H6C | 108.7 |
O71A—C7A—C8A | 111.5 (3) | C5B—C6B—H6D | 108.7 |
C6A—C7A—C8A | 116.6 (3) | C7B—C6B—H6D | 108.7 |
O71A—C7A—H7A | 107.8 | H6C—C6B—H6D | 107.6 |
C6A—C7A—H7A | 107.8 | O71B—C7B—C6B | 105.3 (3) |
C8A—C7A—H7A | 107.8 | O71B—C7B—C8B | 112.0 (3) |
C72A—O71A—C7A | 116.5 (3) | C6B—C7B—C8B | 116.0 (3) |
O73A—C72A—O71A | 123.6 (4) | O71B—C7B—H7B | 107.7 |
O73A—C72A—C74A | 125.2 (4) | C6B—C7B—H7B | 107.7 |
O71A—C72A—C74A | 111.3 (4) | C8B—C7B—H7B | 107.7 |
C72A—C74A—H74A | 109.7 | C72B—O71B—C7B | 116.4 (3) |
C72A—C74A—H74B | 109.0 | O73B—C72B—O71B | 123.6 (4) |
H74A—C74A—H74B | 109.5 | O73B—C72B—C74B | 125.4 (4) |
C72A—C74A—H74C | 109.7 | O71B—C72B—C74B | 111.0 (4) |
H74A—C74A—H74C | 109.3 | C72B—C74B—H74D | 109.0 |
H74B—C74A—H74C | 109.6 | C72B—C74B—H74E | 109.7 |
C7A—C8A—C14A | 117.9 (3) | H74D—C74B—H74E | 109.5 |
C7A—C8A—C9A | 106.6 (3) | C72B—C74B—H74F | 109.6 |
C14A—C8A—C9A | 114.4 (3) | H74D—C74B—H74F | 109.4 |
C7A—C8A—H8A | 105.6 | H74E—C74B—H74F | 109.6 |
C14A—C8A—H8A | 105.6 | C7B—C8B—C14B | 118.1 (3) |
C9A—C8A—H8A | 105.6 | C7B—C8B—C9B | 107.4 (3) |
C10A—C9A—C19A | 104.5 (3) | C14B—C8B—C9B | 114.3 (3) |
C10A—C9A—C8A | 113.0 (3) | C7B—C8B—H8B | 105.3 |
C19A—C9A—C8A | 109.3 (3) | C14B—C8B—H8B | 105.3 |
C10A—C9A—C11A | 110.7 (3) | C9B—C8B—H8B | 105.3 |
C19A—C9A—C11A | 107.7 (3) | C19B—C9B—C10B | 105.2 (3) |
C8A—C9A—C11A | 111.4 (3) | C19B—C9B—C11B | 107.5 (3) |
C5A—C10A—C1A | 121.0 (3) | C10B—C9B—C11B | 111.4 (3) |
C5A—C10A—C9A | 121.9 (3) | C19B—C9B—C8B | 108.7 (3) |
C1A—C10A—C9A | 116.8 (3) | C10B—C9B—C8B | 112.3 (3) |
O111—C11A—C12A | 106.1 (3) | C11B—C9B—C8B | 111.4 (3) |
O111—C11A—C9A | 108.6 (3) | C5B—C10B—C1B | 121.1 (3) |
C12A—C11A—C9A | 117.3 (3) | C5B—C10B—C9B | 122.3 (3) |
O111—C11A—H11A | 108.2 | C1B—C10B—C9B | 116.3 (3) |
C12A—C11A—H11A | 108.2 | O115—C11B—C12B | 106.7 (3) |
C9A—C11A—H11A | 108.2 | O115—C11B—C9B | 109.4 (3) |
C112—O111—C11A | 117.5 (3) | C12B—C11B—C9B | 117.6 (3) |
O113—C112—O111 | 124.1 (4) | O115—C11B—H11E | 107.6 |
O113—C112—C114 | 125.2 (4) | C12B—C11B—H11E | 107.6 |
O111—C112—C114 | 110.7 (4) | C9B—C11B—H11E | 107.6 |
C112—C114—H11B | 109.7 | C116—O115—C11B | 118.6 (3) |
C112—C114—H11C | 109.6 | O117—C116—O115 | 123.7 (5) |
H11B—C114—H11C | 109.4 | O117—C116—C118 | 125.7 (4) |
C112—C114—H11D | 109.3 | O115—C116—C118 | 110.6 (5) |
H11B—C114—H11D | 109.4 | C116—C118—H11F | 110.6 |
H11C—C114—H11D | 109.5 | C116—C118—H11G | 108.6 |
C13A—C12A—C11A | 113.9 (3) | H11F—C118—H11G | 109.4 |
C13A—C12A—H12A | 108.8 | C116—C118—H11H | 109.4 |
C11A—C12A—H12A | 108.8 | H11F—C118—H11H | 109.5 |
C13A—C12A—H12B | 108.8 | H11G—C118—H11H | 109.3 |
C11A—C12A—H12B | 108.8 | C13B—C12B—C11B | 113.1 (3) |
H12A—C12A—H12B | 107.7 | C13B—C12B—H12C | 108.9 |
C12A—C13A—C18A | 110.6 (3) | C11B—C12B—H12C | 108.9 |
C12A—C13A—C17A | 117.8 (3) | C13B—C12B—H12D | 108.9 |
C18A—C13A—C17A | 106.3 (3) | C11B—C12B—H12D | 108.9 |
C12A—C13A—C14A | 107.6 (3) | H12C—C12B—H12D | 107.8 |
C18A—C13A—C14A | 112.8 (3) | C12B—C13B—C18B | 110.8 (3) |
C17A—C13A—C14A | 101.6 (3) | C12B—C13B—C17B | 117.2 (3) |
C15A—C14A—C8A | 117.0 (3) | C18B—C13B—C17B | 106.5 (3) |
C15A—C14A—C30A | 106.1 (3) | C12B—C13B—C14B | 107.4 (3) |
C8A—C14A—C30A | 112.4 (3) | C18B—C13B—C14B | 112.5 (3) |
C15A—C14A—C13A | 100.4 (3) | C17B—C13B—C14B | 102.3 (3) |
C8A—C14A—C13A | 108.7 (3) | C30B—C14B—C15B | 106.1 (3) |
C30A—C14A—C13A | 111.6 (3) | C30B—C14B—C8B | 112.5 (3) |
C14A—C15A—C16A | 104.6 (3) | C15B—C14B—C8B | 116.5 (3) |
C14A—C15A—H15A | 110.8 | C30B—C14B—C13B | 111.9 (3) |
C16A—C15A—H15A | 110.8 | C15B—C14B—C13B | 100.4 (3) |
C14A—C15A—H15B | 110.8 | C8B—C14B—C13B | 108.9 (3) |
C16A—C15A—H15B | 110.8 | C14B—C15B—C16B | 104.5 (3) |
H15A—C15A—H15B | 108.9 | C14B—C15B—H15C | 110.9 |
C17A—C16A—C15A | 107.4 (3) | C16B—C15B—H15C | 110.9 |
C17A—C16A—H16A | 110.2 | C14B—C15B—H15D | 110.9 |
C15A—C16A—H16A | 110.2 | C16B—C15B—H15D | 110.9 |
C17A—C16A—H16B | 110.2 | H15C—C15B—H15D | 108.9 |
C15A—C16A—H16B | 110.2 | C15B—C16B—C17B | 107.8 (3) |
H16A—C16A—H16B | 108.5 | C15B—C16B—H16C | 110.2 |
C16A—C17A—C21A | 112.5 (3) | C17B—C16B—H16C | 110.2 |
C16A—C17A—C13A | 102.9 (3) | C15B—C16B—H16D | 110.2 |
C21A—C17A—C13A | 118.6 (3) | C17B—C16B—H16D | 110.2 |
C16A—C17A—H17A | 107.4 | H16C—C16B—H16D | 108.5 |
C21A—C17A—H17A | 107.4 | C21B—C17B—C13B | 119.0 (3) |
C13A—C17A—H17A | 107.4 | C21B—C17B—C16B | 112.5 (3) |
C13A—C18A—H18A | 109.2 | C13B—C17B—C16B | 102.0 (3) |
C13A—C18A—H18B | 109.4 | C21B—C17B—H17B | 107.6 |
H18A—C18A—H18B | 109.5 | C13B—C17B—H17B | 107.6 |
C13A—C18A—H18C | 110.0 | C16B—C17B—H17B | 107.6 |
H18A—C18A—H18C | 109.4 | C13B—C18B—H18D | 109.3 |
H18B—C18A—H18C | 109.3 | C13B—C18B—H18E | 109.7 |
C9A—C19A—H191 | 109.3 | H18D—C18B—H18E | 109.5 |
C9A—C19A—H192 | 109.7 | C13B—C18B—H18F | 109.6 |
H191—C19A—H192 | 109.7 | H18D—C18B—H18F | 109.4 |
C9A—C19A—H193 | 109.3 | H18E—C18B—H18F | 109.3 |
H191—C19A—H193 | 109.4 | C9B—C19B—H194 | 109.1 |
H192—C19A—H193 | 109.4 | C9B—C19B—H195 | 109.7 |
C21A—C20A—H20A | 109.2 | H194—C19B—H195 | 109.6 |
C21A—C20A—H20B | 108.8 | C9B—C19B—H196 | 109.6 |
H20A—C20A—H20B | 109.8 | H194—C19B—H196 | 109.4 |
C21A—C20A—H20C | 109.6 | H195—C19B—H196 | 109.4 |
H20A—C20A—H20C | 109.8 | C21B—C20B—H20D | 109.7 |
H20B—C20A—H20C | 109.6 | C21B—C20B—H20E | 109.3 |
C20A—C21A—C22A | 110.5 (3) | H20D—C20B—H20E | 109.3 |
C20A—C21A—C17A | 113.3 (3) | C21B—C20B—H20F | 109.3 |
C22A—C21A—C17A | 110.6 (3) | H20D—C20B—H20F | 109.5 |
C20A—C21A—H21A | 107.4 | H20E—C20B—H20F | 109.7 |
C22A—C21A—H21A | 107.4 | C20B—C21B—C22B | 110.1 (3) |
C17A—C21A—H21A | 107.4 | C20B—C21B—C17B | 112.6 (3) |
C23A—C22A—C23D | 99.3 (9) | C22B—C21B—C17B | 113.3 (4) |
C23A—C22A—C21A | 116.0 (3) | C20B—C21B—H21B | 106.8 |
C23D—C22A—C21A | 127.7 (7) | C22B—C21B—H21B | 106.8 |
C23A—C22A—H22A | 108.4 | C17B—C21B—H21B | 106.8 |
C21A—C22A—H22A | 108.4 | C23B—C22B—C21B | 116.5 (4) |
C23A—C22A—H22B | 107.8 | C23B—C22B—H22E | 108.2 |
C21A—C22A—H22B | 108.5 | C21B—C22B—H22E | 108.2 |
H22A—C22A—H22B | 107.5 | C23B—C22B—H22F | 108.2 |
C23D—C22A—H22C | 106.6 | C21B—C22B—H22F | 108.2 |
C21A—C22A—H22C | 105.0 | H22E—C22B—H22F | 107.3 |
C23D—C22A—H22D | 105.0 | C24C—C23B—C22B | 125.0 (6) |
C21A—C22A—H22D | 105.1 | C22B—C23B—C24B | 104.5 (5) |
H22C—C22A—H22D | 105.5 | C22B—C23B—H23E | 110.6 |
C22A—C23A—C24A | 112.0 (4) | C24B—C23B—H23E | 111.1 |
C22A—C23A—H23A | 109.3 | C22B—C23B—H23F | 110.7 |
C24A—C23A—H23A | 110.1 | C24B—C23B—H23F | 111.1 |
H22D—C23A—H23A | 104.5 | H23E—C23B—H23F | 108.8 |
C22A—C23A—H23B | 108.7 | C24C—C23B—H23G | 106.2 |
C24A—C23A—H23B | 109.1 | C22B—C23B—H23G | 105.8 |
H23A—C23A—H23B | 107.5 | C24C—C23B—H23H | 106.1 |
C23A—C24A—C25A | 113.7 (5) | C22B—C23B—H23H | 106.1 |
C23A—C24A—H24A | 109.6 | H23G—C23B—H23H | 106.3 |
C25A—C24A—H24A | 108.7 | C23B—C24B—C25B | 113.2 (7) |
C23A—C24A—H24B | 108.8 | C23B—C24B—H24E | 108.9 |
C25A—C24A—H24B | 108.9 | C25B—C24B—H24E | 108.9 |
H24A—C24A—H24B | 106.8 | C23B—C24B—H24F | 108.9 |
C26A—C25A—C27A | 107.7 (7) | C25B—C24B—H24F | 108.9 |
C26A—C25A—C24A | 112.2 (6) | H24E—C24B—H24F | 107.7 |
C27A—C25A—C24A | 111.2 (6) | C27B—C25B—C24B | 110.7 (12) |
C26A—C25A—H25A | 108.7 | C27B—C25B—C26B | 113.2 (12) |
C27A—C25A—H25A | 107.6 | C24B—C25B—C26B | 108.1 (9) |
C24A—C25A—H25A | 109.3 | C27B—C25B—H25B | 108.2 |
C25A—C26A—H26A | 108.8 | C24B—C25B—H25B | 108.2 |
C25A—C26A—H26B | 108.9 | C26B—C25B—H25B | 108.2 |
H26A—C26A—H26B | 109.6 | C25B—C26B—H26G | 109.6 |
C25A—C26A—H26C | 108.9 | C25B—C26B—H26H | 108.7 |
H26A—C26A—H26C | 110.7 | H26G—C26B—H26H | 109.4 |
H26B—C26A—H26C | 109.8 | C25B—C26B—H26I | 110.1 |
C25A—C27A—H27A | 109.6 | H26G—C26B—H26I | 109.4 |
C25A—C27A—H27B | 111.0 | H26H—C26B—H26I | 109.6 |
H27A—C27A—H27B | 108.8 | C25B—C27B—H27G | 109.3 |
C25A—C27A—H27C | 106.9 | C25B—C27B—H27H | 108.9 |
H27A—C27A—H27C | 109.9 | H27G—C27B—H27H | 109.5 |
H27B—C27A—H27C | 110.6 | C25B—C27B—H27I | 110.1 |
C22A—C23D—C24D | 112.8 (12) | H27G—C27B—H27I | 109.4 |
C22A—C23D—H23C | 109.0 | H27H—C27B—H27I | 109.7 |
C24D—C23D—H23C | 109.0 | C23B—C24C—C25C | 119.1 (9) |
C22A—C23D—H23D | 109.0 | C23B—C24C—H24G | 107.5 |
C24D—C23D—H23D | 109.0 | C25C—C24C—H24G | 107.5 |
H23C—C23D—H23D | 107.8 | C23B—C24C—H24H | 107.5 |
C25D—C24D—C23D | 107.9 (13) | C25C—C24C—H24H | 107.5 |
C25D—C24D—H24C | 110.1 | H24G—C24C—H24H | 107.0 |
C23D—C24D—H24C | 110.1 | C26C—C25C—C27C | 111.8 (11) |
C25D—C24D—H24D | 110.1 | C26C—C25C—C24C | 109.9 (12) |
C23D—C24D—H24D | 110.1 | C27C—C25C—C24C | 108.2 (11) |
H24C—C24D—H24D | 108.4 | C26C—C25C—H25C | 108.9 |
C26D—C25D—C27D | 109.9 (16) | C27C—C25C—H25C | 108.9 |
C26D—C25D—C24D | 108.3 (17) | C24C—C25C—H25C | 108.9 |
C27D—C25D—C24D | 110.6 (15) | C25C—C26C—H26J | 110.0 |
C26D—C25D—H25D | 109.3 | C25C—C26C—H26K | 109.2 |
C27D—C25D—H25D | 109.3 | H26J—C26C—H26K | 109.6 |
C24D—C25D—H25D | 109.3 | C25C—C26C—H26L | 109.1 |
C25D—C26D—H26D | 109.5 | H26J—C26C—H26L | 109.6 |
C25D—C26D—H26E | 109.5 | H26K—C26C—H26L | 109.4 |
H26D—C26D—H26E | 109.5 | C25C—C27C—H27J | 109.1 |
C25D—C26D—H26F | 109.5 | C25C—C27C—H27K | 110.6 |
H26D—C26D—H26F | 109.5 | H27J—C27C—H27K | 109.5 |
H26E—C26D—H26F | 109.5 | C25C—C27C—H27L | 108.7 |
C25D—C27D—H27D | 109.5 | H27J—C27C—H27L | 109.5 |
C25D—C27D—H27E | 109.5 | H27K—C27C—H27L | 109.4 |
H27D—C27D—H27E | 109.5 | C4B—C28B—H284 | 109.6 |
C25D—C27D—H27F | 109.5 | C4B—C28B—H285 | 109.2 |
H27D—C27D—H27F | 109.5 | H284—C28B—H285 | 109.4 |
H27E—C27D—H27F | 109.5 | C4B—C28B—H286 | 109.5 |
C4A—C28A—H281 | 109.8 | H284—C28B—H286 | 109.5 |
C4A—C28A—H282 | 109.1 | H285—C28B—H286 | 109.6 |
H281—C28A—H282 | 109.5 | C4B—C29B—H294 | 109.5 |
C4A—C28A—H283 | 109.4 | C4B—C29B—H295 | 109.3 |
H281—C28A—H283 | 109.6 | H294—C29B—H295 | 109.3 |
H282—C28A—H283 | 109.4 | C4B—C29B—H296 | 109.7 |
C4A—C29A—H291 | 109.3 | H294—C29B—H296 | 109.5 |
C4A—C29A—H292 | 109.5 | H295—C29B—H296 | 109.5 |
H291—C29A—H292 | 109.4 | C14B—C30B—H30D | 109.8 |
C4A—C29A—H293 | 109.6 | C14B—C30B—H30E | 109.3 |
H291—C29A—H293 | 109.5 | H30D—C30B—H30E | 109.3 |
H292—C29A—H293 | 109.5 | C14B—C30B—H30F | 109.5 |
C14A—C30A—H30A | 109.4 | H30D—C30B—H30F | 109.4 |
C14A—C30A—H30B | 109.3 | H30E—C30B—H30F | 109.5 |
| | | |
C10A—C1A—C2A—C3A | −42.5 (5) | C23D—C24D—C25D—C27D | −161.2 (18) |
C1A—C2A—C3A—O31A | −176.9 (3) | C10B—C1B—C2B—C3B | −45.6 (5) |
C1A—C2A—C3A—C4A | 62.4 (4) | C1B—C2B—C3B—O31B | −174.0 (3) |
C2A—C3A—O31A—C32A | 118.9 (4) | C1B—C2B—C3B—C4B | 65.9 (4) |
C4A—C3A—O31A—C32A | −118.1 (4) | C2B—C3B—O31B—C32B | 129.6 (4) |
C3A—O31A—C32A—O33A | 0.7 (6) | C4B—C3B—O31B—C32B | −108.0 (4) |
C3A—O31A—C32A—C34A | −178.6 (3) | C3B—O31B—C32B—O33B | −2.0 (6) |
O31A—C3A—C4A—C28A | −49.3 (4) | C3B—O31B—C32B—C34B | 177.6 (3) |
C2A—C3A—C4A—C28A | 71.0 (4) | O31B—C3B—C4B—C29B | 68.4 (4) |
O31A—C3A—C4A—C29A | 69.2 (4) | C2B—C3B—C4B—C29B | −171.1 (3) |
C2A—C3A—C4A—C29A | −170.5 (3) | O31B—C3B—C4B—C28B | −50.6 (4) |
O31A—C3A—C4A—C5A | −170.4 (3) | C2B—C3B—C4B—C28B | 69.9 (4) |
C2A—C3A—C4A—C5A | −50.0 (4) | O31B—C3B—C4B—C5B | −170.2 (3) |
C28A—C4A—C5A—C10A | −102.3 (4) | C2B—C3B—C4B—C5B | −49.8 (4) |
C29A—C4A—C5A—C10A | 138.4 (4) | C29B—C4B—C5B—C10B | 135.3 (4) |
C3A—C4A—C5A—C10A | 20.2 (5) | C3B—C4B—C5B—C10B | 15.7 (5) |
C28A—C4A—C5A—C6A | 76.3 (4) | C28B—C4B—C5B—C10B | −105.5 (4) |
C29A—C4A—C5A—C6A | −43.0 (4) | C29B—C4B—C5B—C6B | −44.0 (4) |
C3A—C4A—C5A—C6A | −161.3 (3) | C3B—C4B—C5B—C6B | −163.6 (3) |
C10A—C5A—C6A—C7A | 9.8 (5) | C28B—C4B—C5B—C6B | 75.2 (4) |
C4A—C5A—C6A—C7A | −168.8 (3) | C10B—C5B—C6B—C7B | 10.6 (6) |
C5A—C6A—C7A—O71A | −159.7 (3) | C4B—C5B—C6B—C7B | −170.1 (3) |
C5A—C6A—C7A—C8A | −35.7 (5) | C5B—C6B—C7B—O71B | −161.7 (3) |
C6A—C7A—O71A—C72A | −150.4 (3) | C5B—C6B—C7B—C8B | −37.2 (5) |
C8A—C7A—O71A—C72A | 82.4 (4) | C6B—C7B—O71B—C72B | −149.1 (3) |
C7A—O71A—C72A—O73A | 2.0 (5) | C8B—C7B—O71B—C72B | 83.9 (4) |
C7A—O71A—C72A—C74A | −177.8 (3) | C7B—O71B—C72B—O73B | 0.2 (6) |
O71A—C7A—C8A—C14A | 45.4 (4) | C7B—O71B—C72B—C74B | 179.6 (3) |
C6A—C7A—C8A—C14A | −75.2 (4) | O71B—C7B—C8B—C14B | 45.8 (4) |
O71A—C7A—C8A—C9A | 175.7 (3) | C6B—C7B—C8B—C14B | −75.2 (4) |
C6A—C7A—C8A—C9A | 55.1 (4) | O71B—C7B—C8B—C9B | 176.8 (3) |
C7A—C8A—C9A—C10A | −50.0 (4) | C6B—C7B—C8B—C9B | 55.8 (4) |
C14A—C8A—C9A—C10A | 82.2 (4) | C7B—C8B—C9B—C19B | 67.5 (4) |
C7A—C8A—C9A—C19A | 65.8 (4) | C14B—C8B—C9B—C19B | −159.5 (3) |
C14A—C8A—C9A—C19A | −161.9 (3) | C7B—C8B—C9B—C10B | −48.5 (4) |
C7A—C8A—C9A—C11A | −175.3 (3) | C14B—C8B—C9B—C10B | 84.6 (4) |
C14A—C8A—C9A—C11A | −43.1 (4) | C7B—C8B—C9B—C11B | −174.3 (3) |
C6A—C5A—C10A—C1A | 178.6 (3) | C14B—C8B—C9B—C11B | −41.2 (4) |
C4A—C5A—C10A—C1A | −2.9 (6) | C6B—C5B—C10B—C1B | −179.0 (3) |
C6A—C5A—C10A—C9A | −7.8 (6) | C4B—C5B—C10B—C1B | 1.8 (6) |
C4A—C5A—C10A—C9A | 170.7 (3) | C6B—C5B—C10B—C9B | −6.5 (6) |
C2A—C1A—C10A—C5A | 14.1 (5) | C4B—C5B—C10B—C9B | 174.3 (3) |
C2A—C1A—C10A—C9A | −159.8 (3) | C2B—C1B—C10B—C5B | 13.3 (5) |
C19A—C9A—C10A—C5A | −89.2 (4) | C2B—C1B—C10B—C9B | −159.6 (3) |
C8A—C9A—C10A—C5A | 29.4 (5) | C19B—C9B—C10B—C5B | −91.4 (4) |
C11A—C9A—C10A—C5A | 155.1 (3) | C11B—C9B—C10B—C5B | 152.4 (3) |
C19A—C9A—C10A—C1A | 84.6 (4) | C8B—C9B—C10B—C5B | 26.6 (5) |
C8A—C9A—C10A—C1A | −156.7 (3) | C19B—C9B—C10B—C1B | 81.5 (4) |
C11A—C9A—C10A—C1A | −31.0 (4) | C11B—C9B—C10B—C1B | −34.7 (4) |
C10A—C9A—C11A—O111 | 148.2 (3) | C8B—C9B—C10B—C1B | −160.5 (3) |
C19A—C9A—C11A—O111 | 34.6 (4) | C19B—C9B—C11B—O115 | 32.3 (4) |
C8A—C9A—C11A—O111 | −85.2 (3) | C10B—C9B—C11B—O115 | 147.1 (3) |
C10A—C9A—C11A—C12A | −91.6 (4) | C8B—C9B—C11B—O115 | −86.6 (3) |
C19A—C9A—C11A—C12A | 154.8 (3) | C19B—C9B—C11B—C12B | 154.2 (3) |
C8A—C9A—C11A—C12A | 35.0 (4) | C10B—C9B—C11B—C12B | −91.1 (4) |
C12A—C11A—O111—C112 | 116.9 (3) | C8B—C9B—C11B—C12B | 35.2 (4) |
C9A—C11A—O111—C112 | −116.2 (4) | C12B—C11B—O115—C116 | 119.9 (3) |
C11A—O111—C112—O113 | 3.5 (6) | C9B—C11B—O115—C116 | −111.9 (4) |
C11A—O111—C112—C114 | −178.8 (3) | C11B—O115—C116—O117 | 5.0 (6) |
O111—C11A—C12A—C13A | 76.8 (4) | C11B—O115—C116—C118 | −176.3 (4) |
C9A—C11A—C12A—C13A | −44.7 (4) | O115—C11B—C12B—C13B | 76.7 (4) |
C11A—C12A—C13A—C18A | −65.9 (4) | C9B—C11B—C12B—C13B | −46.5 (5) |
C11A—C12A—C13A—C17A | 171.6 (3) | C11B—C12B—C13B—C18B | −63.6 (4) |
C11A—C12A—C13A—C14A | 57.7 (4) | C11B—C12B—C13B—C17B | 174.0 (3) |
C7A—C8A—C14A—C15A | −61.8 (5) | C11B—C12B—C13B—C14B | 59.6 (4) |
C9A—C8A—C14A—C15A | 171.7 (3) | C7B—C8B—C14B—C30B | 60.4 (4) |
C7A—C8A—C14A—C30A | 61.5 (4) | C9B—C8B—C14B—C30B | −67.4 (4) |
C9A—C8A—C14A—C30A | −65.1 (4) | C7B—C8B—C14B—C15B | −62.2 (5) |
C7A—C8A—C14A—C13A | −174.5 (3) | C9B—C8B—C14B—C15B | 169.9 (3) |
C9A—C8A—C14A—C13A | 58.9 (4) | C7B—C8B—C14B—C13B | −174.9 (3) |
C12A—C13A—C14A—C15A | 172.3 (3) | C9B—C8B—C14B—C13B | 57.3 (4) |
C18A—C13A—C14A—C15A | −65.4 (4) | C12B—C13B—C14B—C30B | 60.1 (4) |
C17A—C13A—C14A—C15A | 47.9 (3) | C18B—C13B—C14B—C30B | −177.8 (3) |
C12A—C13A—C14A—C8A | −64.4 (4) | C17B—C13B—C14B—C30B | −63.9 (4) |
C18A—C13A—C14A—C8A | 57.9 (4) | C12B—C13B—C14B—C15B | 172.3 (3) |
C17A—C13A—C14A—C8A | 171.3 (3) | C18B—C13B—C14B—C15B | −65.6 (3) |
C12A—C13A—C14A—C30A | 60.2 (4) | C17B—C13B—C14B—C15B | 48.3 (3) |
C18A—C13A—C14A—C30A | −177.6 (3) | C12B—C13B—C14B—C8B | −64.9 (4) |
C17A—C13A—C14A—C30A | −64.2 (4) | C18B—C13B—C14B—C8B | 57.2 (4) |
C8A—C14A—C15A—C16A | −155.4 (3) | C17B—C13B—C14B—C8B | 171.1 (3) |
C30A—C14A—C15A—C16A | 78.2 (4) | C30B—C14B—C15B—C16B | 78.2 (4) |
C13A—C14A—C15A—C16A | −38.1 (4) | C8B—C14B—C15B—C16B | −155.9 (3) |
C14A—C15A—C16A—C17A | 14.4 (4) | C13B—C14B—C15B—C16B | −38.5 (4) |
C15A—C16A—C17A—C21A | 144.5 (3) | C14B—C15B—C16B—C17B | 15.3 (4) |
C15A—C16A—C17A—C13A | 15.6 (4) | C12B—C13B—C17B—C21B | 80.1 (4) |
C12A—C13A—C17A—C16A | −156.2 (3) | C18B—C13B—C17B—C21B | −44.5 (4) |
C18A—C13A—C17A—C16A | 79.1 (3) | C14B—C13B—C17B—C21B | −162.8 (3) |
C14A—C13A—C17A—C16A | −39.0 (3) | C12B—C13B—C17B—C16B | −155.5 (3) |
C12A—C13A—C17A—C21A | 78.9 (4) | C18B—C13B—C17B—C16B | 79.9 (3) |
C18A—C13A—C17A—C21A | −45.8 (4) | C14B—C13B—C17B—C16B | −38.4 (4) |
C14A—C13A—C17A—C21A | −163.9 (3) | C15B—C16B—C17B—C21B | 143.3 (3) |
C16A—C17A—C21A—C20A | −180.0 (3) | C15B—C16B—C17B—C13B | 14.7 (4) |
C13A—C17A—C21A—C20A | −59.9 (4) | C13B—C17B—C21B—C20B | −62.1 (4) |
C16A—C17A—C21A—C22A | 55.4 (4) | C16B—C17B—C21B—C20B | 178.8 (3) |
C13A—C17A—C21A—C22A | 175.5 (3) | C13B—C17B—C21B—C22B | 172.1 (4) |
C20A—C21A—C22A—C23A | −60.2 (5) | C16B—C17B—C21B—C22B | 53.0 (5) |
C17A—C21A—C22A—C23A | 66.0 (5) | C20B—C21B—C22B—C23B | −68.7 (5) |
C20A—C21A—C22A—C23D | 67.0 (12) | C17B—C21B—C22B—C23B | 58.5 (6) |
C17A—C21A—C22A—C23D | −166.8 (11) | C21B—C22B—C23B—C24C | 150.1 (8) |
C23D—C22A—C23A—C24A | 36.7 (9) | C21B—C22B—C23B—C24B | −173.7 (6) |
C21A—C22A—C23A—C24A | 177.0 (5) | C24C—C23B—C24B—C25B | −59.1 (10) |
C22A—C23A—C24A—C25A | 177.0 (5) | C22B—C23B—C24B—C25B | 172.0 (8) |
C23A—C24A—C25A—C26A | 69.6 (7) | C23B—C24B—C25B—C27B | 56.6 (14) |
C23A—C24A—C25A—C27A | −169.7 (7) | C23B—C24B—C25B—C26B | −67.9 (13) |
C23A—C22A—C23D—C24D | −48.1 (17) | C22B—C23B—C24C—C25C | 174.1 (9) |
C21A—C22A—C23D—C24D | 178.4 (12) | C24B—C23B—C24C—C25C | 107.2 (15) |
C22A—C23D—C24D—C25D | −173.2 (15) | C23B—C24C—C25C—C26C | 170.3 (10) |
C23D—C24D—C25D—C26D | 78 (2) | C23B—C24C—C25C—C27C | −67.3 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2A—H2A2···O117i | 0.99 | 2.58 | 3.512 (6) | 156 |
C21A—H21A···O73Aii | 1.00 | 2.55 | 3.298 (5) | 132 |
C29A—H292···O73B | 0.96 | 2.49 | 3.437 (5) | 171 |
C2B—H2B2···O113iii | 0.99 | 2.66 | 3.482 (6) | 140 |
C34B—H34F···O117iv | 0.96 | 2.40 | 3.354 (5) | 175 |
C74B—H74F···O33Av | 0.96 | 2.62 | 3.577 (6) | 172 |
C21B—H21B···O73Bv | 1.00 | 2.54 | 3.308 (5) | 133 |
C29B—H295···O73A | 0.96 | 2.53 | 3.469 (5) | 167 |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z+2; (iii) x+1, y, z; (iv) −x+2, y−1/2, −z+3/2; (v) x+1/2, −y+5/2, −z+2. |
(II) 3
β,7
α,11
β-triacetoxy-5
α-cucurbit-1(10)-ene
top
Crystal data top
C36H58O6 | F(000) = 1288 |
Mr = 586.82 | Dx = 1.130 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2975 reflections |
a = 9.0958 (9) Å | θ = 4–20° |
b = 14.8510 (16) Å | µ = 0.08 mm−1 |
c = 25.526 (2) Å | T = 190 K |
V = 3448.1 (6) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.3 × 0.1 mm |
Data collection top
Kuma KM-4 CCD four-circle diffractometer | 2124 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.081 |
Graphite monochromator | θmax = 27.0°, θmin = 3.2° |
ω scans | h = −8→11 |
16585 measured reflections | k = −17→18 |
4159 independent reflections | l = −32→32 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.020P)2] where P = (Fo2 + 2Fc2)/3 |
4159 reflections | (Δ/σ)max = 0.001 |
412 parameters | Δρmax = 0.19 e Å−3 |
8 restraints | Δρmin = −0.18 e Å−3 |
Crystal data top
C36H58O6 | V = 3448.1 (6) Å3 |
Mr = 586.82 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.0958 (9) Å | µ = 0.08 mm−1 |
b = 14.8510 (16) Å | T = 190 K |
c = 25.526 (2) Å | 0.35 × 0.3 × 0.1 mm |
Data collection top
Kuma KM-4 CCD four-circle diffractometer | 2124 reflections with I > 2σ(I) |
16585 measured reflections | Rint = 0.081 |
4159 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.055 | 8 restraints |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.19 e Å−3 |
4159 reflections | Δρmin = −0.18 e Å−3 |
412 parameters | |
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 | Occ. (<1) |
C1 | 0.2225 (4) | 0.8639 (3) | 0.11343 (14) | 0.0425 (10) | |
H1 | 0.2058 | 0.9255 | 0.1215 | 0.051* | |
C2 | 0.1538 (4) | 0.8281 (2) | 0.06404 (14) | 0.0501 (12) | |
H2A | 0.2098 | 0.8503 | 0.0334 | 0.060* | |
H2B | 0.0519 | 0.8510 | 0.0611 | 0.060* | |
C3 | 0.1515 (4) | 0.7260 (3) | 0.06325 (14) | 0.0391 (10) | |
H3 | 0.1307 | 0.7045 | 0.0269 | 0.047* | |
O31 | 0.0313 (3) | 0.69973 (17) | 0.09766 (9) | 0.0454 (7) | |
C32 | −0.0689 (5) | 0.6408 (3) | 0.07975 (17) | 0.0422 (11) | |
O33 | −0.0626 (3) | 0.60277 (17) | 0.03824 (11) | 0.0607 (9) | |
C34 | −0.1909 (4) | 0.6314 (3) | 0.11934 (15) | 0.0620 (13) | |
H34A | −0.2626 | 0.5871 | 0.1068 | 0.093* | |
H34B | −0.2395 | 0.6897 | 0.1241 | 0.093* | |
H34C | −0.1499 | 0.6112 | 0.1528 | 0.093* | |
C4 | 0.2968 (4) | 0.6851 (2) | 0.08247 (14) | 0.0351 (10) | |
C5 | 0.3335 (4) | 0.7179 (2) | 0.13862 (12) | 0.0309 (9) | |
H5 | 0.4420 | 0.7097 | 0.1429 | 0.037* | |
C6 | 0.2619 (4) | 0.6643 (2) | 0.18339 (12) | 0.0318 (9) | |
H6A | 0.1643 | 0.6422 | 0.1720 | 0.038* | |
H6B | 0.3236 | 0.6113 | 0.1918 | 0.038* | |
C7 | 0.2440 (4) | 0.7221 (2) | 0.23197 (13) | 0.0320 (9) | |
H7 | 0.1513 | 0.7573 | 0.2272 | 0.038* | |
O71 | 0.2218 (3) | 0.66492 (14) | 0.27813 (8) | 0.0344 (6) | |
C72 | 0.0861 (5) | 0.6280 (2) | 0.28386 (15) | 0.0348 (10) | |
O73 | −0.0149 (3) | 0.63993 (16) | 0.25451 (10) | 0.0458 (7) | |
C74 | 0.0808 (4) | 0.5713 (2) | 0.33248 (13) | 0.0458 (11) | |
H74A | −0.0183 | 0.5464 | 0.3368 | 0.069* | |
H74B | 0.1054 | 0.6084 | 0.3630 | 0.069* | |
H74C | 0.1517 | 0.5219 | 0.3294 | 0.069* | |
C8 | 0.3647 (4) | 0.7902 (2) | 0.24498 (13) | 0.0302 (9) | |
H8 | 0.3215 | 0.8276 | 0.2737 | 0.036* | |
C9 | 0.3772 (4) | 0.8586 (2) | 0.19617 (13) | 0.0320 (9) | |
C10 | 0.3049 (4) | 0.8169 (2) | 0.14692 (13) | 0.0308 (9) | |
C11 | 0.5404 (4) | 0.8729 (2) | 0.18193 (13) | 0.0332 (9) | |
H11 | 0.5766 | 0.8174 | 0.1638 | 0.040* | |
O111 | 0.5475 (3) | 0.94728 (15) | 0.14501 (9) | 0.0399 (7) | |
C112 | 0.6291 (5) | 0.9350 (3) | 0.10202 (17) | 0.0532 (13) | |
O113 | 0.7052 (4) | 0.8710 (2) | 0.09366 (12) | 0.0786 (11) | |
C114 | 0.6156 (5) | 1.0146 (3) | 0.06527 (14) | 0.0693 (15) | |
H11A | 0.6750 | 1.0037 | 0.0339 | 0.104* | |
H11B | 0.6506 | 1.0691 | 0.0829 | 0.104* | |
H11C | 0.5124 | 1.0225 | 0.0552 | 0.104* | |
C12 | 0.6455 (4) | 0.8941 (2) | 0.22737 (13) | 0.0334 (10) | |
H12A | 0.6421 | 0.9596 | 0.2344 | 0.040* | |
H12B | 0.7470 | 0.8791 | 0.2164 | 0.040* | |
C13 | 0.6109 (4) | 0.8430 (2) | 0.27890 (13) | 0.0297 (9) | |
C14 | 0.5137 (4) | 0.7581 (2) | 0.26744 (14) | 0.0290 (9) | |
C15 | 0.5096 (4) | 0.7142 (2) | 0.32243 (13) | 0.0373 (10) | |
H15A | 0.4864 | 0.6493 | 0.3200 | 0.045* | |
H15B | 0.4354 | 0.7438 | 0.3450 | 0.045* | |
C16 | 0.6670 (4) | 0.7290 (2) | 0.34427 (14) | 0.0380 (10) | |
H16A | 0.7226 | 0.6717 | 0.3437 | 0.046* | |
H16B | 0.6622 | 0.7507 | 0.3809 | 0.046* | |
C17 | 0.7451 (4) | 0.8009 (2) | 0.30876 (13) | 0.0320 (9) | |
H17 | 0.8058 | 0.7675 | 0.2825 | 0.038* | |
C18 | 0.5369 (4) | 0.9083 (2) | 0.31886 (13) | 0.0368 (10) | |
H18A | 0.5140 | 0.8756 | 0.3512 | 0.055* | |
H18B | 0.4460 | 0.9324 | 0.3037 | 0.055* | |
H18C | 0.6042 | 0.9580 | 0.3268 | 0.055* | |
C19 | 0.3040 (4) | 0.9487 (2) | 0.21009 (12) | 0.0403 (10) | |
H19A | 0.2007 | 0.9383 | 0.2191 | 0.061* | |
H19B | 0.3098 | 0.9894 | 0.1800 | 0.061* | |
H19C | 0.3549 | 0.9757 | 0.2400 | 0.061* | |
C20 | 0.9172 (4) | 0.9358 (2) | 0.30391 (14) | 0.0435 (11) | |
H20A | 0.9804 | 0.9753 | 0.3248 | 0.065* | |
H20B | 0.8388 | 0.9714 | 0.2877 | 0.065* | |
H20C | 0.9760 | 0.9067 | 0.2765 | 0.065* | |
C21 | 0.8492 (4) | 0.8638 (2) | 0.33933 (14) | 0.0366 (9) | |
H21 | 0.7909 | 0.8948 | 0.3672 | 0.044* | |
C22 | 0.9721 (4) | 0.8094 (2) | 0.36591 (14) | 0.0402 (10) | |
H22A | 0.9275 | 0.7571 | 0.3840 | 0.048* | |
H22B | 1.0387 | 0.7857 | 0.3385 | 0.048* | |
C23 | 1.0632 (4) | 0.8630 (3) | 0.40554 (15) | 0.0547 (12) | |
H23A | 1.1023 | 0.9176 | 0.3882 | 0.066* | |
H23B | 0.9985 | 0.8827 | 0.4345 | 0.066* | |
C24 | 1.1907 (4) | 0.8093 (3) | 0.42810 (16) | 0.0548 (12) | |
H24A | 1.2406 | 0.7782 | 0.3991 | 0.066* | 0.631 (13) |
H24B | 1.1501 | 0.7619 | 0.4518 | 0.066* | 0.631 (13) |
H24C | 1.2732 | 0.8134 | 0.4035 | 0.066* | 0.369 (13) |
H24D | 1.1606 | 0.7450 | 0.4301 | 0.066* | 0.369 (13) |
C25 | 1.3078 (11) | 0.8649 (8) | 0.4593 (4) | 0.056 (3) | 0.631 (13) |
H25 | 1.3431 | 0.9139 | 0.4355 | 0.067* | 0.631 (13) |
C26 | 1.4422 (12) | 0.8086 (10) | 0.4745 (5) | 0.106 (5) | 0.631 (13) |
H26A | 1.4137 | 0.7637 | 0.5008 | 0.138* | 0.631 (13) |
H26B | 1.5182 | 0.8481 | 0.4891 | 0.138* | 0.631 (13) |
H26C | 1.4808 | 0.7779 | 0.4434 | 0.138* | 0.631 (13) |
C27 | 1.2440 (13) | 0.9094 (9) | 0.5067 (4) | 0.093 (5) | 0.631 (13) |
H27A | 1.3172 | 0.9499 | 0.5221 | 0.121* | 0.631 (13) |
H27B | 1.2163 | 0.8634 | 0.5324 | 0.121* | 0.631 (13) |
H27C | 1.1568 | 0.9440 | 0.4966 | 0.121* | 0.631 (13) |
C25A | 1.247 (2) | 0.8357 (10) | 0.4824 (8) | 0.073 (7) | 0.369 (13) |
H25A | 1.1668 | 0.8398 | 0.5089 | 0.087* | 0.369 (13) |
C26A | 1.367 (2) | 0.7680 (13) | 0.4981 (9) | 0.097 (8) | 0.369 (13) |
H26D | 1.4098 | 0.7860 | 0.5317 | 0.126* | 0.369 (13) |
H26E | 1.4437 | 0.7668 | 0.4712 | 0.126* | 0.369 (13) |
H26F | 1.3232 | 0.7079 | 0.5015 | 0.126* | 0.369 (13) |
C27A | 1.319 (2) | 0.9269 (15) | 0.4714 (8) | 0.093 (7) | 0.369 (13) |
H27D | 1.2420 | 0.9718 | 0.4647 | 0.120* | 0.369 (13) |
H27E | 1.3828 | 0.9220 | 0.4407 | 0.120* | 0.369 (13) |
H27F | 1.3770 | 0.9453 | 0.5019 | 0.120* | 0.369 (13) |
C28 | 0.4188 (4) | 0.7167 (2) | 0.04478 (13) | 0.0496 (11) | |
H28A | 0.3963 | 0.6962 | 0.0092 | 0.074* | |
H28B | 0.5133 | 0.6915 | 0.0559 | 0.074* | |
H28C | 0.4243 | 0.7826 | 0.0453 | 0.074* | |
C29 | 0.2905 (4) | 0.5818 (2) | 0.07981 (13) | 0.0419 (10) | |
H29A | 0.2656 | 0.5631 | 0.0441 | 0.063* | |
H29B | 0.2154 | 0.5596 | 0.1041 | 0.063* | |
H29C | 0.3864 | 0.5568 | 0.0895 | 0.063* | |
C30 | 0.5982 (4) | 0.6887 (2) | 0.23299 (13) | 0.0352 (10) | |
H30A | 0.5276 | 0.6520 | 0.2133 | 0.053* | |
H30B | 0.6577 | 0.6496 | 0.2555 | 0.053* | |
H30C | 0.6625 | 0.7207 | 0.2085 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.049 (3) | 0.028 (2) | 0.050 (3) | 0.003 (2) | −0.007 (2) | −0.002 (2) |
C2 | 0.059 (3) | 0.042 (3) | 0.049 (3) | 0.006 (2) | −0.013 (2) | 0.003 (2) |
C3 | 0.043 (3) | 0.047 (3) | 0.027 (2) | −0.004 (2) | −0.007 (2) | 0.004 (2) |
O31 | 0.0408 (17) | 0.0513 (19) | 0.0442 (18) | 0.0005 (15) | −0.0011 (15) | −0.0080 (14) |
C32 | 0.044 (3) | 0.035 (3) | 0.048 (3) | 0.006 (2) | −0.004 (3) | 0.007 (2) |
O33 | 0.078 (2) | 0.0544 (19) | 0.0496 (19) | −0.0178 (16) | 0.0020 (19) | −0.0109 (16) |
C34 | 0.042 (3) | 0.080 (3) | 0.064 (3) | 0.007 (3) | 0.005 (3) | 0.001 (3) |
C4 | 0.041 (3) | 0.030 (2) | 0.034 (2) | −0.0005 (19) | 0.001 (2) | −0.0029 (18) |
C5 | 0.029 (2) | 0.032 (2) | 0.032 (2) | −0.0010 (18) | −0.0040 (18) | 0.0019 (19) |
C6 | 0.042 (3) | 0.026 (2) | 0.027 (2) | −0.0004 (18) | −0.0033 (19) | 0.0025 (17) |
C7 | 0.033 (2) | 0.030 (2) | 0.034 (2) | −0.0022 (19) | −0.0008 (19) | 0.0074 (19) |
O71 | 0.0354 (16) | 0.0316 (15) | 0.0363 (16) | −0.0039 (12) | 0.0030 (13) | 0.0049 (12) |
C72 | 0.036 (3) | 0.025 (2) | 0.043 (3) | −0.001 (2) | 0.008 (2) | −0.007 (2) |
O73 | 0.0327 (16) | 0.0521 (18) | 0.0526 (18) | 0.0013 (14) | −0.0058 (15) | −0.0018 (14) |
C74 | 0.051 (3) | 0.046 (3) | 0.041 (3) | −0.002 (2) | 0.010 (2) | 0.004 (2) |
C8 | 0.034 (2) | 0.025 (2) | 0.031 (2) | 0.0010 (18) | 0.0054 (19) | −0.0021 (18) |
C9 | 0.037 (2) | 0.023 (2) | 0.036 (2) | 0.0041 (19) | −0.0010 (19) | 0.0065 (19) |
C10 | 0.035 (2) | 0.023 (2) | 0.035 (2) | 0.0013 (18) | 0.0003 (19) | 0.0019 (18) |
C11 | 0.040 (3) | 0.025 (2) | 0.035 (2) | 0.000 (2) | 0.002 (2) | 0.0062 (18) |
O111 | 0.0489 (18) | 0.0341 (15) | 0.0366 (16) | −0.0021 (14) | 0.0024 (15) | 0.0101 (13) |
C112 | 0.060 (4) | 0.058 (3) | 0.041 (3) | −0.016 (3) | 0.001 (3) | 0.005 (3) |
O113 | 0.090 (3) | 0.076 (2) | 0.070 (2) | 0.010 (2) | 0.041 (2) | 0.0128 (19) |
C114 | 0.098 (4) | 0.066 (3) | 0.044 (3) | −0.017 (3) | −0.002 (3) | 0.021 (2) |
C12 | 0.030 (2) | 0.031 (2) | 0.039 (2) | −0.0002 (18) | 0.003 (2) | 0.0031 (19) |
C13 | 0.031 (2) | 0.031 (2) | 0.027 (2) | −0.0010 (17) | −0.0015 (18) | 0.0016 (18) |
C14 | 0.031 (2) | 0.026 (2) | 0.030 (2) | −0.0010 (17) | 0.0006 (19) | 0.0025 (17) |
C15 | 0.044 (3) | 0.030 (2) | 0.038 (2) | −0.0061 (19) | 0.001 (2) | 0.0033 (18) |
C16 | 0.045 (3) | 0.030 (2) | 0.038 (2) | −0.0012 (19) | −0.009 (2) | 0.0042 (19) |
C17 | 0.031 (2) | 0.031 (2) | 0.034 (2) | 0.0044 (19) | −0.0025 (19) | 0.0002 (18) |
C18 | 0.041 (2) | 0.027 (2) | 0.043 (3) | 0.0010 (18) | −0.005 (2) | −0.0037 (18) |
C19 | 0.044 (3) | 0.032 (2) | 0.045 (3) | 0.0019 (19) | −0.008 (2) | 0.0005 (18) |
C20 | 0.039 (3) | 0.043 (3) | 0.049 (3) | −0.002 (2) | −0.006 (2) | 0.003 (2) |
C21 | 0.033 (2) | 0.034 (2) | 0.042 (2) | −0.0027 (19) | −0.001 (2) | 0.000 (2) |
C22 | 0.037 (2) | 0.040 (2) | 0.044 (2) | 0.001 (2) | −0.006 (2) | 0.0021 (19) |
C23 | 0.055 (3) | 0.053 (3) | 0.056 (3) | 0.010 (2) | −0.020 (2) | −0.005 (2) |
C24 | 0.045 (3) | 0.070 (3) | 0.049 (3) | 0.020 (2) | −0.006 (2) | −0.005 (2) |
C25 | 0.048 (7) | 0.059 (8) | 0.059 (7) | −0.003 (6) | −0.021 (5) | 0.002 (6) |
C26 | 0.053 (7) | 0.166 (14) | 0.099 (10) | 0.030 (8) | −0.021 (6) | −0.012 (8) |
C27 | 0.093 (9) | 0.103 (10) | 0.083 (8) | 0.032 (7) | −0.033 (7) | −0.048 (7) |
C25A | 0.046 (12) | 0.082 (14) | 0.091 (17) | 0.002 (10) | −0.013 (10) | 0.011 (12) |
C26A | 0.113 (19) | 0.082 (14) | 0.094 (16) | 0.039 (13) | −0.078 (15) | −0.012 (11) |
C27A | 0.088 (16) | 0.125 (19) | 0.065 (15) | −0.008 (14) | −0.047 (12) | −0.020 (14) |
C28 | 0.052 (3) | 0.064 (3) | 0.033 (2) | −0.001 (2) | 0.003 (2) | −0.002 (2) |
C29 | 0.053 (3) | 0.041 (3) | 0.032 (2) | 0.003 (2) | −0.004 (2) | −0.0051 (18) |
C30 | 0.043 (2) | 0.023 (2) | 0.040 (2) | 0.0026 (18) | −0.004 (2) | −0.0046 (18) |
Geometric parameters (Å, º) top
C1—C10 | 1.333 (4) | C15—H15B | 0.9900 |
C1—C2 | 1.504 (5) | C16—C17 | 1.570 (4) |
C1—H1 | 0.9500 | C16—H16A | 0.9900 |
C2—C3 | 1.516 (4) | C16—H16B | 0.9900 |
C2—H2A | 0.9900 | C17—C21 | 1.542 (4) |
C2—H2B | 0.9900 | C17—H17 | 1.0000 |
C3—O31 | 1.456 (4) | C18—H18A | 0.9800 |
C3—C4 | 1.535 (4) | C18—H18B | 0.9800 |
C3—H3 | 1.0000 | C18—H18C | 0.9800 |
O31—C32 | 1.344 (4) | C19—H19A | 0.9800 |
C32—O33 | 1.202 (4) | C19—H19B | 0.9800 |
C32—C34 | 1.507 (5) | C19—H19C | 0.9800 |
C34—H34A | 0.9800 | C20—C21 | 1.531 (4) |
C34—H34B | 0.9800 | C20—H20A | 0.9800 |
C34—H34C | 0.9800 | C20—H20B | 0.9800 |
C4—C29 | 1.536 (4) | C20—H20C | 0.9800 |
C4—C28 | 1.542 (5) | C21—C22 | 1.537 (4) |
C4—C5 | 1.550 (4) | C21—H21 | 1.0000 |
C5—C10 | 1.508 (4) | C22—C23 | 1.531 (4) |
C5—C6 | 1.538 (4) | C22—H22A | 0.9900 |
C5—H5 | 1.0000 | C22—H22B | 0.9900 |
C6—C7 | 1.517 (4) | C23—C24 | 1.521 (5) |
C6—H6A | 0.9900 | C23—H23A | 0.9900 |
C6—H6B | 0.9900 | C23—H23B | 0.9900 |
C7—O71 | 1.466 (3) | C24—C25A | 1.529 (16) |
C7—C8 | 1.530 (4) | C24—C25 | 1.565 (10) |
C7—H7 | 1.0000 | C24—H24A | 0.9830 |
O71—C72 | 1.359 (4) | C24—H24B | 0.9987 |
C72—O73 | 1.198 (4) | C24—H24C | 0.9806 |
C72—C74 | 1.501 (4) | C24—H24D | 0.9946 |
C74—H74A | 0.9800 | C25—C27 | 1.497 (12) |
C74—H74B | 0.9800 | C25—C26 | 1.532 (11) |
C74—H74C | 0.9800 | C25—H25 | 1.0000 |
C8—C14 | 1.547 (4) | C26—H26A | 0.9800 |
C8—C9 | 1.611 (4) | C26—H26B | 0.9800 |
C8—H8 | 1.0000 | C26—H26C | 0.9800 |
C9—C19 | 1.535 (4) | C27—H27A | 0.9800 |
C9—C11 | 1.543 (5) | C27—H27B | 0.9800 |
C9—C10 | 1.548 (5) | C27—H27C | 0.9800 |
C11—O111 | 1.454 (4) | C25A—C27A | 1.526 (18) |
C11—C12 | 1.536 (4) | C25A—C26A | 1.534 (16) |
C11—H11 | 1.0000 | C25A—H25A | 1.0000 |
O111—C112 | 1.337 (5) | C26A—H26D | 0.9800 |
C112—O113 | 1.195 (5) | C26A—H26E | 0.9800 |
C112—C114 | 1.514 (5) | C26A—H26F | 0.9800 |
C114—H11A | 0.9800 | C27A—H27D | 0.9800 |
C114—H11B | 0.9800 | C27A—H27E | 0.9800 |
C114—H11C | 0.9800 | C27A—H27F | 0.9800 |
C12—C13 | 1.551 (4) | C28—H28A | 0.9800 |
C12—H12A | 0.9900 | C28—H28B | 0.9800 |
C12—H12B | 0.9900 | C28—H28C | 0.9800 |
C13—C18 | 1.560 (4) | C29—H29A | 0.9800 |
C13—C14 | 1.568 (4) | C29—H29B | 0.9800 |
C13—C17 | 1.569 (4) | C29—H29C | 0.9800 |
C14—C15 | 1.548 (4) | C30—H30A | 0.9800 |
C14—C30 | 1.558 (4) | C30—H30B | 0.9800 |
C15—C16 | 1.552 (4) | C30—H30C | 0.9800 |
C15—H15A | 0.9900 | | |
| | | |
C10—C1—C2 | 125.9 (4) | C14—C15—C16 | 104.1 (3) |
C10—C1—H1 | 117.1 | C14—C15—H15A | 110.9 |
C2—C1—H1 | 117.1 | C16—C15—H15A | 110.9 |
C1—C2—C3 | 111.7 (3) | C14—C15—H15B | 110.9 |
C1—C2—H2A | 109.3 | C16—C15—H15B | 110.9 |
C3—C2—H2A | 109.3 | H15A—C15—H15B | 109.0 |
C1—C2—H2B | 109.3 | C15—C16—C17 | 107.8 (3) |
C3—C2—H2B | 109.3 | C15—C16—H16A | 110.1 |
H2A—C2—H2B | 107.9 | C17—C16—H16A | 110.1 |
O31—C3—C2 | 105.7 (3) | C15—C16—H16B | 110.1 |
O31—C3—C4 | 110.3 (3) | C17—C16—H16B | 110.1 |
C2—C3—C4 | 112.3 (3) | H16A—C16—H16B | 108.5 |
O31—C3—H3 | 109.5 | C21—C17—C13 | 118.8 (3) |
C2—C3—H3 | 109.5 | C21—C17—C16 | 113.4 (3) |
C4—C3—H3 | 109.5 | C13—C17—C16 | 101.5 (3) |
C32—O31—C3 | 118.6 (3) | C21—C17—H17 | 107.5 |
O33—C32—O31 | 125.0 (4) | C13—C17—H17 | 107.5 |
O33—C32—C34 | 125.6 (4) | C16—C17—H17 | 107.5 |
O31—C32—C34 | 109.4 (4) | C13—C18—H18A | 109.5 |
C32—C34—H34A | 109.5 | C13—C18—H18B | 109.5 |
C32—C34—H34B | 109.5 | H18A—C18—H18B | 109.5 |
H34A—C34—H34B | 109.5 | C13—C18—H18C | 109.5 |
C32—C34—H34C | 109.5 | H18A—C18—H18C | 109.5 |
H34A—C34—H34C | 109.5 | H18B—C18—H18C | 109.5 |
H34B—C34—H34C | 109.5 | C9—C19—H19A | 109.5 |
C3—C4—C29 | 110.4 (3) | C9—C19—H19B | 109.5 |
C3—C4—C28 | 107.4 (3) | H19A—C19—H19B | 109.5 |
C29—C4—C28 | 107.7 (3) | C9—C19—H19C | 109.5 |
C3—C4—C5 | 110.9 (3) | H19A—C19—H19C | 109.5 |
C29—C4—C5 | 111.3 (3) | H19B—C19—H19C | 109.5 |
C28—C4—C5 | 109.0 (3) | C21—C20—H20A | 109.5 |
C10—C5—C6 | 109.1 (3) | C21—C20—H20B | 109.5 |
C10—C5—C4 | 113.5 (3) | H20A—C20—H20B | 109.5 |
C6—C5—C4 | 115.7 (3) | C21—C20—H20C | 109.5 |
C10—C5—H5 | 105.9 | H20A—C20—H20C | 109.5 |
C6—C5—H5 | 105.9 | H20B—C20—H20C | 109.5 |
C4—C5—H5 | 105.9 | C20—C21—C22 | 109.5 (3) |
C7—C6—C5 | 111.1 (3) | C20—C21—C17 | 111.9 (3) |
C7—C6—H6A | 109.4 | C22—C21—C17 | 110.6 (3) |
C5—C6—H6A | 109.4 | C20—C21—H21 | 108.3 |
C7—C6—H6B | 109.4 | C22—C21—H21 | 108.3 |
C5—C6—H6B | 109.4 | C17—C21—H21 | 108.3 |
H6A—C6—H6B | 108.0 | C23—C22—C21 | 114.3 (3) |
O71—C7—C6 | 110.1 (2) | C23—C22—H22A | 108.7 |
O71—C7—C8 | 107.9 (3) | C21—C22—H22A | 108.7 |
C6—C7—C8 | 118.4 (3) | C23—C22—H22B | 108.7 |
O71—C7—H7 | 106.6 | C21—C22—H22B | 108.7 |
C6—C7—H7 | 106.6 | H22A—C22—H22B | 107.6 |
C8—C7—H7 | 106.6 | C24—C23—C22 | 113.0 (3) |
C72—O71—C7 | 116.4 (3) | C24—C23—H23A | 109.0 |
O73—C72—O71 | 124.7 (3) | C22—C23—H23A | 109.0 |
O73—C72—C74 | 125.1 (4) | C24—C23—H23B | 109.0 |
O71—C72—C74 | 110.2 (3) | C22—C23—H23B | 109.0 |
C72—C74—H74A | 109.5 | H23A—C23—H23B | 107.8 |
C72—C74—H74B | 109.5 | C23—C24—C25A | 117.7 (7) |
H74A—C74—H74B | 109.5 | C23—C24—C25 | 115.7 (5) |
C72—C74—H74C | 109.5 | C23—C24—H24A | 108.2 |
H74A—C74—H74C | 109.5 | C25—C24—H24A | 108.4 |
H74B—C74—H74C | 109.5 | C23—C24—H24B | 108.5 |
C7—C8—C14 | 120.3 (3) | C25—C24—H24B | 108.4 |
C7—C8—C9 | 107.4 (3) | H24A—C24—H24B | 107.3 |
C14—C8—C9 | 114.8 (3) | C23—C24—H24C | 107.9 |
C7—C8—H8 | 104.1 | C25A—C24—H24C | 107.9 |
C14—C8—H8 | 104.1 | C23—C24—H24D | 108.2 |
C9—C8—H8 | 104.1 | C25A—C24—H24D | 107.1 |
C19—C9—C11 | 110.6 (3) | H24C—C24—H24D | 107.6 |
C19—C9—C10 | 110.6 (3) | C27—C25—C26 | 110.1 (8) |
C11—C9—C10 | 105.8 (3) | C27—C25—C24 | 112.4 (10) |
C19—C9—C8 | 109.8 (3) | C26—C25—C24 | 112.6 (9) |
C11—C9—C8 | 109.7 (3) | C27—C25—H25 | 107.1 |
C10—C9—C8 | 110.2 (3) | C26—C25—H25 | 107.1 |
C1—C10—C5 | 121.1 (3) | C24—C25—H25 | 107.1 |
C1—C10—C9 | 123.4 (3) | C27A—C25A—C24 | 101.9 (16) |
C5—C10—C9 | 115.5 (3) | C27A—C25A—C26A | 109.2 (17) |
O111—C11—C12 | 107.8 (3) | C24—C25A—C26A | 107.9 (14) |
O111—C11—C9 | 107.4 (3) | C27A—C25A—H25A | 112.4 |
C12—C11—C9 | 116.7 (3) | C24—C25A—H25A | 112.4 |
O111—C11—H11 | 108.2 | C26A—C25A—H25A | 112.4 |
C12—C11—H11 | 108.2 | C25A—C26A—H26D | 109.5 |
C9—C11—H11 | 108.2 | C25A—C26A—H26E | 109.5 |
C112—O111—C11 | 117.0 (3) | H26D—C26A—H26E | 109.5 |
O113—C112—O111 | 125.2 (4) | C25A—C26A—H26F | 109.5 |
O113—C112—C114 | 123.9 (4) | H26D—C26A—H26F | 109.5 |
O111—C112—C114 | 111.0 (4) | H26E—C26A—H26F | 109.5 |
C112—C114—H11A | 109.5 | C25A—C27A—H27D | 109.5 |
C112—C114—H11B | 109.5 | C25A—C27A—H27E | 109.5 |
H11A—C114—H11B | 109.5 | H27D—C27A—H27E | 109.5 |
C112—C114—H11C | 109.5 | C25A—C27A—H27F | 109.5 |
H11A—C114—H11C | 109.5 | H27D—C27A—H27F | 109.5 |
H11B—C114—H11C | 109.5 | H27E—C27A—H27F | 109.5 |
C11—C12—C13 | 114.5 (3) | C4—C28—H28A | 109.5 |
C11—C12—H12A | 108.6 | C4—C28—H28B | 109.5 |
C13—C12—H12A | 108.6 | H28A—C28—H28B | 109.5 |
C11—C12—H12B | 108.6 | C4—C28—H28C | 109.5 |
C13—C12—H12B | 108.6 | H28A—C28—H28C | 109.5 |
H12A—C12—H12B | 107.6 | H28B—C28—H28C | 109.5 |
C12—C13—C18 | 109.7 (3) | C4—C29—H29A | 109.5 |
C12—C13—C14 | 110.5 (3) | C4—C29—H29B | 109.5 |
C18—C13—C14 | 112.2 (3) | H29A—C29—H29B | 109.5 |
C12—C13—C17 | 116.7 (3) | C4—C29—H29C | 109.5 |
C18—C13—C17 | 105.4 (3) | H29A—C29—H29C | 109.5 |
C14—C13—C17 | 102.1 (3) | H29B—C29—H29C | 109.5 |
C8—C14—C15 | 116.4 (3) | C14—C30—H30A | 109.5 |
C8—C14—C30 | 115.3 (3) | C14—C30—H30B | 109.5 |
C15—C14—C30 | 104.2 (3) | H30A—C30—H30B | 109.5 |
C8—C14—C13 | 108.4 (2) | C14—C30—H30C | 109.5 |
C15—C14—C13 | 100.5 (3) | H30A—C30—H30C | 109.5 |
C30—C14—C13 | 111.1 (3) | H30B—C30—H30C | 109.5 |
| | | |
C10—C1—C2—C3 | 16.0 (6) | C8—C9—C11—C12 | −48.1 (4) |
C1—C2—C3—O31 | 77.1 (4) | C12—C11—O111—C112 | 101.1 (3) |
C1—C2—C3—C4 | −43.2 (4) | C9—C11—O111—C112 | −132.3 (3) |
C2—C3—O31—C32 | 129.3 (3) | C11—O111—C112—O113 | −6.3 (6) |
C4—C3—O31—C32 | −109.0 (3) | C11—O111—C112—C114 | 175.1 (3) |
C3—O31—C32—O33 | 5.2 (6) | O111—C11—C12—C13 | 158.1 (3) |
C3—O31—C32—C34 | −173.8 (3) | C9—C11—C12—C13 | 37.2 (4) |
O31—C3—C4—C29 | 63.6 (4) | C11—C12—C13—C18 | −104.4 (3) |
C2—C3—C4—C29 | −178.7 (3) | C11—C12—C13—C14 | 19.9 (4) |
O31—C3—C4—C28 | −179.2 (3) | C11—C12—C13—C17 | 135.8 (3) |
C2—C3—C4—C28 | −61.6 (4) | C7—C8—C14—C15 | −65.3 (4) |
O31—C3—C4—C5 | −60.2 (4) | C9—C8—C14—C15 | 164.0 (3) |
C2—C3—C4—C5 | 57.5 (4) | C7—C8—C14—C30 | 57.3 (4) |
C3—C4—C5—C10 | −42.5 (4) | C9—C8—C14—C30 | −73.5 (3) |
C29—C4—C5—C10 | −165.8 (3) | C7—C8—C14—C13 | −177.6 (3) |
C28—C4—C5—C10 | 75.6 (4) | C9—C8—C14—C13 | 51.7 (4) |
C3—C4—C5—C6 | 84.8 (4) | C12—C13—C14—C8 | −63.4 (3) |
C29—C4—C5—C6 | −38.5 (4) | C18—C13—C14—C8 | 59.4 (3) |
C28—C4—C5—C6 | −157.2 (3) | C17—C13—C14—C8 | 171.8 (3) |
C10—C5—C6—C7 | −24.4 (4) | C12—C13—C14—C15 | 174.0 (3) |
C4—C5—C6—C7 | −153.8 (3) | C18—C13—C14—C15 | −63.2 (3) |
C5—C6—C7—O71 | −161.6 (3) | C17—C13—C14—C15 | 49.3 (3) |
C5—C6—C7—C8 | −36.9 (4) | C12—C13—C14—C30 | 64.2 (3) |
C6—C7—O71—C72 | −76.5 (3) | C18—C13—C14—C30 | −173.0 (3) |
C8—C7—O71—C72 | 153.0 (3) | C17—C13—C14—C30 | −60.6 (3) |
C7—O71—C72—O73 | −1.0 (5) | C8—C14—C15—C16 | −155.3 (3) |
C7—O71—C72—C74 | 179.7 (3) | C30—C14—C15—C16 | 76.5 (3) |
O71—C7—C8—C14 | 51.5 (4) | C13—C14—C15—C16 | −38.6 (3) |
C6—C7—C8—C14 | −74.3 (4) | C14—C15—C16—C17 | 14.2 (3) |
O71—C7—C8—C9 | −174.6 (2) | C12—C13—C17—C21 | 74.6 (4) |
C6—C7—C8—C9 | 59.5 (4) | C18—C13—C17—C21 | −47.5 (4) |
C7—C8—C9—C19 | 103.8 (3) | C14—C13—C17—C21 | −164.9 (3) |
C14—C8—C9—C19 | −119.5 (3) | C12—C13—C17—C16 | −160.3 (3) |
C7—C8—C9—C11 | −134.5 (3) | C18—C13—C17—C16 | 77.6 (3) |
C14—C8—C9—C11 | 2.3 (4) | C14—C13—C17—C16 | −39.8 (3) |
C7—C8—C9—C10 | −18.4 (4) | C15—C16—C17—C21 | 144.6 (3) |
C14—C8—C9—C10 | 118.4 (3) | C15—C16—C17—C13 | 16.0 (3) |
C2—C1—C10—C5 | −2.2 (6) | C13—C17—C21—C20 | −58.0 (4) |
C2—C1—C10—C9 | 177.8 (3) | C16—C17—C21—C20 | −177.1 (3) |
C6—C5—C10—C1 | −114.8 (4) | C13—C17—C21—C22 | 179.6 (3) |
C4—C5—C10—C1 | 15.7 (5) | C16—C17—C21—C22 | 60.5 (4) |
C6—C5—C10—C9 | 65.2 (4) | C20—C21—C22—C23 | 67.5 (4) |
C4—C5—C10—C9 | −164.2 (3) | C17—C21—C22—C23 | −168.8 (3) |
C19—C9—C10—C1 | 17.8 (5) | C21—C22—C23—C24 | −175.8 (3) |
C11—C9—C10—C1 | −102.1 (4) | C22—C23—C24—C25A | −154.1 (9) |
C8—C9—C10—C1 | 139.4 (3) | C22—C23—C24—C25 | 167.3 (5) |
C19—C9—C10—C5 | −162.3 (3) | C23—C24—C25—C27 | 62.4 (12) |
C11—C9—C10—C5 | 77.9 (3) | C25A—C24—C25—C27 | −39.7 (12) |
C8—C9—C10—C5 | −40.6 (4) | C23—C24—C25—C26 | −172.5 (7) |
C19—C9—C11—O111 | −47.9 (4) | C25A—C24—C25—C26 | 85.3 (17) |
C10—C9—C11—O111 | 71.9 (3) | C23—C24—C25A—C27A | −69.3 (19) |
C8—C9—C11—O111 | −169.2 (2) | C25—C24—C25A—C27A | 26.5 (13) |
C19—C9—C11—C12 | 73.2 (3) | C23—C24—C25A—C26A | 175.8 (12) |
C10—C9—C11—C12 | −167.0 (3) | C25—C24—C25A—C26A | −88 (2) |
Crystal data top
C36H58O6 | Dx = 1.007 Mg m−3 |
Mr = 586.82 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 10862 reflections |
a = 14.4800 (12) Å | θ = 2.0–27.9° |
b = 19.8818 (13) Å | µ = 0.07 mm−1 |
c = 26.882 (2) Å | T = 295 K |
V = 7739.0 (10) Å3 | Block, colourless |
Z = 8 | 0.5 × 0.2 × 0.2 mm |
F(000) = 2576 | |
Data collection top
Kuma KM-4 CCD four-circle diffractometer | 3204 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.097 |
Graphite monochromator | θmax = 25.5°, θmin = 2.1° |
/w scan | h = −17→17 |
71201 measured reflections | k = −24→24 |
7878 independent reflections | l = −32→30 |
Refinement top
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)] = 0.095 | H-atom parameters constrained |
wR(F2) = 0.276 | w = 1/[σ2(Fo2) + (0.150P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.004 |
7878 reflections | Δρmax = 0.59 e Å−3 |
786 parameters | Δρmin = −0.39 e Å−3 |
205 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | |
Crystal data top
C36H58O6 | V = 7739.0 (10) Å3 |
Mr = 586.82 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 14.4800 (12) Å | µ = 0.07 mm−1 |
b = 19.8818 (13) Å | T = 295 K |
c = 26.882 (2) Å | 0.5 × 0.2 × 0.2 mm |
Data collection top
Kuma KM-4 CCD four-circle diffractometer | 3204 reflections with I > 2σ(I) |
71201 measured reflections | Rint = 0.097 |
7878 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.095 | 205 restraints |
wR(F2) = 0.276 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.59 e Å−3 |
7878 reflections | Δρmin = −0.39 e Å−3 |
786 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Special details top
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. |
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 > 2sigma(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 | Occ. (<1) |
C1A | 0.1836 (6) | 1.0200 (3) | 0.8419 (3) | 0.072 (2) | |
H1A1 | 0.1778 | 0.9847 | 0.8171 | 0.086* | |
H1A2 | 0.1249 | 1.0233 | 0.8591 | 0.086* | |
C2A | 0.2015 (8) | 1.0852 (4) | 0.8155 (3) | 0.102 (3) | |
H2A1 | 0.1450 | 1.1015 | 0.8004 | 0.122* | |
H2A2 | 0.2469 | 1.0786 | 0.7895 | 0.122* | |
C3A | 0.2376 (6) | 1.1374 (4) | 0.8538 (3) | 0.074 (2) | |
H3A | 0.1910 | 1.1421 | 0.8800 | 0.089* | |
O31A | 0.2473 (4) | 1.2010 (3) | 0.8298 (2) | 0.0976 (18) | |
C32A | 0.1890 (9) | 1.2520 (5) | 0.8435 (4) | 0.104 (3) | |
O33A | 0.1376 (6) | 1.2503 (3) | 0.8754 (3) | 0.134 (3) | |
C34A | 0.2132 (10) | 1.3141 (4) | 0.8136 (4) | 0.150 (5) | |
H34A | 0.1788 | 1.3521 | 0.8275 | 0.195* | |
H34B | 0.2800 | 1.3240 | 0.8138 | 0.195* | |
H34C | 0.1926 | 1.3059 | 0.7793 | 0.195* | |
C4A | 0.3259 (6) | 1.1175 (4) | 0.8777 (3) | 0.075 (2) | |
C5A | 0.3215 (5) | 1.0426 (3) | 0.8951 (3) | 0.0654 (19) | |
C6A | 0.3942 (5) | 1.0243 (3) | 0.9325 (3) | 0.076 (2) | |
H6A | 0.3808 | 1.0469 | 0.9636 | 0.091* | |
H6B | 0.4536 | 1.0402 | 0.9208 | 0.091* | |
C7A | 0.4002 (5) | 0.9482 (3) | 0.9419 (3) | 0.0672 (19) | |
H7A | 0.4389 | 0.9287 | 0.9158 | 0.081* | |
O71A | 0.4505 (4) | 0.9428 (2) | 0.9889 (2) | 0.0789 (15) | |
C72A | 0.5071 (6) | 0.8891 (5) | 0.9948 (4) | 0.087 (3) | |
O73A | 0.5194 (4) | 0.8491 (3) | 0.9620 (3) | 0.111 (2) | |
C74A | 0.5501 (6) | 0.8890 (5) | 1.0457 (4) | 0.106 (3) | |
H74A | 0.6164 | 0.8777 | 1.0435 | 0.137* | |
H74B | 0.5432 | 0.9337 | 1.0600 | 0.137* | |
H74C | 0.5184 | 0.8564 | 1.0670 | 0.137* | |
C8A | 0.3100 (4) | 0.9102 (3) | 0.9427 (2) | 0.0533 (17) | |
H8A | 0.3273 | 0.8625 | 0.9425 | 0.064* | |
C9A | 0.2625 (5) | 0.9226 (3) | 0.8919 (2) | 0.0605 (18) | |
C10A | 0.2567 (5) | 0.9994 (3) | 0.8789 (3) | 0.0639 (18) | |
C11A | 0.1647 (6) | 0.8895 (3) | 0.8902 (3) | 0.067 (2) | |
H11A | 0.1287 | 0.9124 | 0.8643 | 0.080* | |
O111 | 0.1756 (4) | 0.8191 (2) | 0.87527 (18) | 0.0768 (14) | |
C112 | 0.1386 (8) | 0.7995 (5) | 0.8322 (4) | 0.094 (3) | |
O113 | 0.0979 (7) | 0.8367 (4) | 0.8037 (2) | 0.131 (3) | |
C114 | 0.1537 (8) | 0.7246 (4) | 0.8241 (3) | 0.116 (3) | |
H11B | 0.2199 | 0.7168 | 0.8176 | 0.151* | |
H11C | 0.1346 | 0.6989 | 0.8535 | 0.151* | |
H11D | 0.1170 | 0.7105 | 0.7952 | 0.151* | |
C12A | 0.1079 (5) | 0.8893 (3) | 0.9375 (2) | 0.0590 (18) | |
H12A | 0.0826 | 0.9339 | 0.9426 | 0.071* | |
H12B | 0.0565 | 0.8585 | 0.9334 | 0.071* | |
C13A | 0.1614 (5) | 0.8693 (3) | 0.9829 (2) | 0.0602 (18) | |
C14A | 0.2452 (5) | 0.9186 (3) | 0.9881 (3) | 0.0564 (17) | |
C15A | 0.2828 (5) | 0.8966 (4) | 1.0384 (3) | 0.067 (2) | |
H15A | 0.3203 | 0.9319 | 1.0530 | 0.081* | |
H15B | 0.3204 | 0.8565 | 1.0349 | 0.081* | |
C16A | 0.1980 (6) | 0.8823 (4) | 1.0709 (3) | 0.083 (2) | |
H16A | 0.1887 | 0.9185 | 1.0946 | 0.099* | |
H16B | 0.2062 | 0.8406 | 1.0891 | 0.099* | |
C17A | 0.1136 (5) | 0.8769 (3) | 1.0351 (3) | 0.0670 (19) | |
H17A | 0.0824 | 0.9206 | 1.0354 | 0.080* | |
C18A | 0.1951 (5) | 0.7947 (3) | 0.9796 (3) | 0.0645 (19) | |
H18A | 0.2363 | 0.7901 | 0.9507 | 0.084* | |
H18B | 0.2290 | 0.7822 | 1.0100 | 0.084* | |
H18C | 0.1412 | 0.7652 | 0.9755 | 0.084* | |
C19A | 0.3214 (6) | 0.8921 (4) | 0.8496 (3) | 0.084 (2) | |
H191 | 0.3779 | 0.9189 | 0.8452 | 0.110* | |
H192 | 0.3386 | 0.8462 | 0.8586 | 0.110* | |
H193 | 0.2857 | 0.8917 | 0.8185 | 0.110* | |
C20A | −0.0378 (6) | 0.8151 (4) | 1.0182 (3) | 0.093 (2) | |
H20A | −0.0173 | 0.7938 | 0.9874 | 0.122* | |
H20B | −0.0856 | 0.7877 | 1.0343 | 0.122* | |
H20C | −0.0634 | 0.8594 | 1.0108 | 0.122* | |
C21A | 0.0427 (5) | 0.8239 (4) | 1.0522 (3) | 0.079 (2) | |
H21A | 0.0749 | 0.7806 | 1.0539 | 0.095* | |
C22A | 0.0075 (4) | 0.8397 (3) | 1.1044 (2) | 0.113 (3) | |
H22A | −0.0305 | 0.8000 | 1.1155 | 0.135* | 0.587 (7) |
H22B | 0.0641 | 0.8425 | 1.1270 | 0.135* | 0.587 (7) |
H22C | 0.0653 | 0.8539 | 1.1234 | 0.135* | 0.413 (7) |
H22D | −0.0331 | 0.8809 | 1.1023 | 0.135* | 0.413 (7) |
C23A | −0.0469 (4) | 0.9045 (3) | 1.1143 (2) | 0.149 (6) | 0.587 (7) |
H23A | −0.0093 | 0.9442 | 1.1051 | 0.178* | 0.587 (7) |
H23B | −0.1015 | 0.9030 | 1.0917 | 0.178* | 0.587 (7) |
C24A | −0.0976 (4) | 0.9066 (3) | 1.1642 (2) | 0.209 (8) | 0.587 (7) |
H24A | −0.1379 | 0.8679 | 1.1725 | 0.251* | 0.587 (7) |
H24B | −0.0430 | 0.9046 | 1.1868 | 0.251* | 0.587 (7) |
C25A | −0.1364 (4) | 0.9778 (3) | 1.1732 (2) | 0.207 (8) | 0.587 (7) |
H25A | −0.0990 | 1.0172 | 1.1611 | 0.248* | 0.587 (7) |
C26A | −0.2381 (4) | 0.9772 (3) | 1.1842 (2) | 0.222 (9) | 0.587 (7) |
H26A | −0.2731 | 0.9377 | 1.1943 | 0.289* | 0.587 (7) |
H26B | −0.2723 | 1.0177 | 1.1943 | 0.289* | 0.587 (7) |
H26C | −0.2284 | 0.9774 | 1.1484 | 0.289* | 0.587 (7) |
C27A | −0.0790 (4) | 1.0123 (3) | 1.2135 (2) | 0.241 (10) | 0.587 (7) |
H27A | −0.0191 | 1.0194 | 1.2306 | 0.289* | 0.587 (7) |
H27B | −0.1195 | 1.0509 | 1.2198 | 0.289* | 0.587 (7) |
H27C | −0.1080 | 0.9717 | 1.2256 | 0.289* | 0.587 (7) |
C23D | −0.0303 (4) | 0.7836 (3) | 1.1379 (2) | 0.075 (5) | 0.413 (7) |
H23C | 0.0194 | 0.7511 | 1.1412 | 0.090* | 0.413 (7) |
H23D | −0.0833 | 0.7605 | 1.1239 | 0.090* | 0.413 (7) |
C24D | −0.0509 (4) | 0.8118 (3) | 1.1897 (2) | 0.093 (5) | 0.413 (7) |
H24C | 0.0033 | 0.8316 | 1.2051 | 0.112* | 0.413 (7) |
H24D | −0.0974 | 0.8466 | 1.1865 | 0.112* | 0.413 (7) |
C25D | −0.0853 (4) | 0.7557 (3) | 1.2247 (2) | 0.083 (5) | 0.413 (7) |
H25D | −0.1312 | 0.7272 | 1.2081 | 0.100* | 0.413 (7) |
C26D | −0.0051 (4) | 0.7104 (3) | 1.2395 (2) | 0.113 (7) | 0.413 (7) |
H26D | −0.0235 | 0.6736 | 1.2604 | 0.148* | 0.413 (7) |
H26E | 0.0341 | 0.7402 | 1.2580 | 0.148* | 0.413 (7) |
H26F | 0.0278 | 0.6935 | 1.2112 | 0.148* | 0.413 (7) |
C27D | −0.1306 (4) | 0.7873 (3) | 1.2707 (2) | 0.090 (6) | 0.413 (7) |
H27D | −0.1814 | 0.8153 | 1.2607 | 0.117* | 0.413 (7) |
H27E | −0.0827 | 0.8147 | 1.2847 | 0.117* | 0.413 (7) |
H27F | −0.1514 | 0.7554 | 1.2950 | 0.117* | 0.413 (7) |
C28A | 0.4064 (7) | 1.1253 (5) | 0.8418 (4) | 0.125 (4) | |
H281 | 0.4106 | 1.1716 | 0.8301 | 0.162* | |
H282 | 0.4650 | 1.1126 | 0.8579 | 0.162* | |
H283 | 0.3948 | 1.0957 | 0.8133 | 0.162* | |
C29A | 0.3418 (6) | 1.1643 (4) | 0.9223 (3) | 0.091 (3) | |
H291 | 0.2976 | 1.1554 | 0.9494 | 0.118* | |
H292 | 0.4054 | 1.1578 | 0.9345 | 0.118* | |
H293 | 0.3343 | 1.2105 | 0.9109 | 0.118* | |
C30A | 0.2113 (5) | 0.9936 (3) | 0.9940 (3) | 0.070 (2) | |
H30A | 0.2648 | 1.0233 | 0.9991 | 0.091* | |
H30B | 0.1776 | 1.0072 | 0.9640 | 0.091* | |
H30C | 0.1697 | 0.9965 | 1.0229 | 0.091* | |
C1B | 0.9027 (6) | 0.9791 (3) | 0.8376 (3) | 0.081 (2) | |
H1B1 | 0.9053 | 1.0136 | 0.8122 | 0.097* | |
H1B2 | 0.9626 | 0.9773 | 0.8537 | 0.097* | |
C2B | 0.8831 (7) | 0.9085 (4) | 0.8122 (3) | 0.084 (2) | |
H2B1 | 0.8336 | 0.9129 | 0.7881 | 0.101* | |
H2B2 | 0.9379 | 0.8925 | 0.7951 | 0.101* | |
C3B | 0.8562 (5) | 0.8602 (4) | 0.8515 (3) | 0.070 (2) | |
H3B | 0.9059 | 0.8571 | 0.8762 | 0.084* | |
O31B | 0.8439 (4) | 0.7953 (3) | 0.8275 (2) | 0.0858 (16) | |
C32B | 0.8920 (8) | 0.7428 (5) | 0.8445 (4) | 0.094 (3) | |
O33B | 0.9453 (6) | 0.7448 (3) | 0.8794 (3) | 0.124 (2) | |
C34B | 0.8723 (9) | 0.6808 (4) | 0.8128 (4) | 0.138 (4) | |
H34D | 0.8880 | 0.6422 | 0.8336 | 0.179* | |
H34E | 0.8059 | 0.6796 | 0.8046 | 0.179* | |
H34F | 0.9090 | 0.6793 | 0.7820 | 0.179* | |
C4B | 0.7637 (5) | 0.8788 (3) | 0.8787 (3) | 0.069 (2) | |
C5B | 0.7699 (5) | 0.9541 (3) | 0.8941 (3) | 0.0586 (17) | |
C6B | 0.6987 (5) | 0.9722 (3) | 0.9319 (3) | 0.075 (2) | |
H6C | 0.6395 | 0.9542 | 0.9215 | 0.090* | |
H6D | 0.7153 | 0.9503 | 0.9629 | 0.090* | |
C7B | 0.6890 (5) | 1.0474 (3) | 0.9425 (3) | 0.069 (2) | |
H7B | 0.6482 | 1.0660 | 0.9168 | 0.083* | |
O71B | 0.6413 (3) | 1.0542 (2) | 0.9897 (2) | 0.0741 (14) | |
C72B | 0.5857 (6) | 1.1069 (5) | 0.9953 (4) | 0.081 (2) | |
O73B | 0.5732 (5) | 1.1486 (3) | 0.9647 (3) | 0.114 (2) | |
C74B | 0.5434 (7) | 1.1092 (5) | 1.0438 (4) | 0.116 (3) | |
H74D | 0.4761 | 1.1164 | 1.0411 | 0.151* | |
H74E | 0.5552 | 1.0654 | 1.0587 | 0.151* | |
H74F | 0.5708 | 1.1441 | 1.0648 | 0.151* | |
C8B | 0.7786 (5) | 1.0868 (3) | 0.9407 (3) | 0.0615 (19) | |
H8B | 0.7603 | 1.1343 | 0.9398 | 0.074* | |
C9B | 0.8258 (5) | 1.0729 (3) | 0.8883 (3) | 0.0613 (18) | |
C10B | 0.8294 (5) | 0.9981 (3) | 0.8758 (2) | 0.0575 (17) | |
C11B | 0.9211 (5) | 1.1083 (3) | 0.8846 (2) | 0.0601 (18) | |
H11E | 0.9567 | 1.0851 | 0.8588 | 0.072* | |
O115 | 0.9095 (4) | 1.1786 (2) | 0.86821 (18) | 0.0741 (14) | |
C116 | 0.9459 (7) | 1.1950 (5) | 0.8235 (4) | 0.093 (3) | |
O117 | 0.9816 (6) | 1.1574 (4) | 0.7956 (3) | 0.129 (3) | |
C118 | 0.9343 (8) | 1.2705 (5) | 0.8172 (4) | 0.127 (4) | |
H11F | 0.9581 | 1.2844 | 0.7846 | 0.165* | |
H11G | 0.8679 | 1.2812 | 0.8195 | 0.165* | |
H11H | 0.9682 | 1.2941 | 0.8436 | 0.165* | |
C12B | 0.9819 (5) | 1.1104 (3) | 0.9319 (2) | 0.0617 (18) | |
H12C | 1.0080 | 1.0661 | 0.9375 | 0.074* | |
H12D | 1.0327 | 1.1413 | 0.9264 | 0.074* | |
C13B | 0.9285 (4) | 1.1326 (3) | 0.9775 (2) | 0.0552 (17) | |
C14B | 0.8457 (5) | 1.0812 (3) | 0.9846 (3) | 0.0577 (17) | |
C15B | 0.8108 (6) | 1.1022 (4) | 1.0363 (3) | 0.076 (2) | |
H15C | 0.7752 | 1.0666 | 1.0518 | 0.091* | |
H15D | 0.7720 | 1.1418 | 1.0333 | 0.091* | |
C16B | 0.8980 (6) | 1.1191 (4) | 1.0662 (3) | 0.079 (2) | |
H16C | 0.9102 | 1.0832 | 1.0897 | 0.095* | |
H16D | 0.8895 | 1.1607 | 1.0845 | 0.095* | |
C17B | 0.9784 (5) | 1.1264 (4) | 1.0281 (3) | 0.071 (2) | |
H17B | 1.0114 | 1.0834 | 1.0278 | 0.086* | |
C18B | 0.8949 (5) | 1.2053 (3) | 0.9727 (3) | 0.070 (2) | |
H18D | 0.8476 | 1.2082 | 0.9464 | 0.091* | |
H18E | 0.8676 | 1.2194 | 1.0045 | 0.091* | |
H18F | 0.9473 | 1.2345 | 0.9644 | 0.091* | |
C19B | 0.7622 (6) | 1.1042 (4) | 0.8468 (3) | 0.078 (2) | |
H194 | 0.7042 | 1.0787 | 0.8441 | 0.101* | |
H195 | 0.7480 | 1.1502 | 0.8567 | 0.101* | |
H196 | 0.7940 | 1.1045 | 0.8145 | 0.101* | |
C20B | 1.1282 (5) | 1.1893 (4) | 1.0060 (3) | 0.087 (2) | |
H20D | 1.1059 | 1.2081 | 0.9745 | 0.113* | |
H20E | 1.1758 | 1.2187 | 1.0202 | 0.113* | |
H20F | 1.1550 | 1.1450 | 0.9999 | 0.113* | |
C21B | 1.0496 (6) | 1.1810 (4) | 1.0429 (3) | 0.085 (2) | |
H21B | 1.0155 | 1.2236 | 1.0431 | 0.102* | |
C22B | 1.0844 (7) | 1.1738 (5) | 1.0957 (3) | 0.122 (3) | |
H22E | 1.1225 | 1.2121 | 1.1043 | 0.147* | |
H22F | 1.0325 | 1.1730 | 1.1185 | 0.147* | |
C23B | 1.1437 (6) | 1.1118 (4) | 1.1050 (3) | 0.152 (4) | |
H23E | 1.2042 | 1.1086 | 1.0858 | 0.183* | 0.354 (14) |
H23F | 1.1035 | 1.0719 | 1.0966 | 0.183* | 0.354 (14) |
H23G | 1.1701 | 1.0950 | 1.0724 | 0.183* | 0.646 (14) |
H23H | 1.0938 | 1.0789 | 1.1153 | 0.183* | 0.646 (14) |
C24B | 1.1876 (6) | 1.1174 (4) | 1.1570 (3) | 0.153 (8) | 0.354 (14) |
H24E | 1.2496 | 1.1356 | 1.1542 | 0.184* | 0.354 (14) |
H24F | 1.1528 | 1.1533 | 1.1728 | 0.184* | 0.354 (14) |
C25B | 1.2623 (6) | 1.0684 (4) | 1.1699 (3) | 0.169 (9) | 0.354 (14) |
H25B | 1.2772 | 1.0870 | 1.2027 | 0.203* | 0.354 (14) |
C26B | 1.2308 (6) | 1.0092 (4) | 1.2014 (3) | 0.192 (12) | 0.354 (14) |
H26G | 1.2580 | 0.9650 | 1.2073 | 0.249* | 0.354 (14) |
H26H | 1.1842 | 1.0188 | 1.2271 | 0.249* | 0.354 (14) |
H26I | 1.2010 | 1.0099 | 1.1685 | 0.249* | 0.354 (14) |
C27B | 1.3267 (6) | 1.0506 (4) | 1.1281 (3) | 0.140 (10) | 0.354 (14) |
H27G | 1.3140 | 1.0453 | 1.0924 | 0.169* | 0.354 (14) |
H27H | 1.3737 | 1.0855 | 1.1328 | 0.169* | 0.354 (14) |
H27I | 1.3499 | 1.0083 | 1.1417 | 0.169* | 0.354 (14) |
C24C | 1.2055 (6) | 1.1094 (4) | 1.1510 (3) | 0.167 (6) | 0.646 (14) |
H24G | 1.1700 | 1.1234 | 1.1798 | 0.200* | 0.646 (14) |
H24H | 1.2545 | 1.1418 | 1.1456 | 0.200* | 0.646 (14) |
C25C | 1.2431 (6) | 1.0383 (4) | 1.1636 (3) | 0.181 (7) | 0.646 (14) |
H25C | 1.2739 | 1.0202 | 1.1341 | 0.217* | 0.646 (14) |
C26C | 1.3011 (6) | 1.0450 (4) | 1.2126 (3) | 0.201 (8) | 0.646 (14) |
H26J | 1.3141 | 1.0024 | 1.2292 | 0.261* | 0.646 (14) |
H26K | 1.3539 | 1.0572 | 1.1913 | 0.261* | 0.646 (14) |
H26L | 1.2914 | 1.0799 | 1.2377 | 0.261* | 0.646 (14) |
C27C | 1.1598 (6) | 0.9930 (4) | 1.1796 (3) | 0.253 (10) | 0.646 (14) |
H27J | 1.1427 | 1.0162 | 1.2104 | 0.304* | 0.646 (14) |
H27K | 1.1049 | 0.9887 | 1.1582 | 0.304* | 0.646 (14) |
H27L | 1.1838 | 0.9485 | 1.1877 | 0.304* | 0.646 (14) |
C28B | 0.6811 (6) | 0.8702 (4) | 0.8432 (3) | 0.097 (3) | |
H284 | 0.6245 | 0.8786 | 0.8626 | 0.126* | |
H285 | 0.6840 | 0.9015 | 0.8151 | 0.126* | |
H286 | 0.6800 | 0.8243 | 0.8304 | 0.126* | |
C29B | 0.7538 (7) | 0.8330 (4) | 0.9241 (3) | 0.090 (2) | |
H294 | 0.8055 | 0.8408 | 0.9472 | 0.117* | |
H295 | 0.6947 | 0.8412 | 0.9413 | 0.117* | |
H296 | 0.7557 | 0.7867 | 0.9123 | 0.117* | |
C30B | 0.8816 (5) | 1.0096 (3) | 0.9921 (3) | 0.0646 (19) | |
H30D | 0.8297 | 0.9803 | 1.0014 | 0.084* | |
H30E | 0.9084 | 0.9944 | 0.9605 | 0.084* | |
H30F | 0.9293 | 1.0083 | 1.0182 | 0.084* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.100 (6) | 0.061 (5) | 0.055 (4) | −0.001 (4) | 0.000 (4) | 0.006 (4) |
C2A | 0.153 (8) | 0.069 (6) | 0.083 (6) | −0.022 (6) | −0.018 (6) | 0.017 (5) |
C3A | 0.091 (6) | 0.062 (5) | 0.070 (5) | 0.009 (5) | 0.009 (5) | 0.016 (4) |
O31A | 0.131 (5) | 0.051 (3) | 0.110 (4) | 0.003 (4) | 0.018 (4) | 0.022 (3) |
C32A | 0.157 (10) | 0.066 (6) | 0.090 (7) | 0.023 (7) | 0.002 (7) | 0.015 (5) |
O33A | 0.188 (8) | 0.092 (5) | 0.123 (6) | 0.046 (5) | 0.045 (6) | 0.015 (4) |
C34A | 0.222 (13) | 0.064 (6) | 0.164 (10) | −0.009 (8) | −0.012 (10) | 0.041 (6) |
C4A | 0.085 (6) | 0.053 (4) | 0.088 (6) | −0.010 (4) | 0.019 (5) | 0.010 (4) |
C5A | 0.079 (5) | 0.047 (4) | 0.070 (5) | −0.005 (4) | 0.012 (4) | 0.000 (4) |
C6A | 0.065 (5) | 0.049 (4) | 0.114 (6) | −0.008 (4) | −0.001 (5) | 0.010 (4) |
C7A | 0.070 (5) | 0.058 (4) | 0.074 (5) | 0.013 (4) | 0.000 (4) | −0.005 (4) |
O71A | 0.078 (3) | 0.060 (3) | 0.099 (4) | 0.006 (3) | −0.012 (3) | −0.001 (3) |
C72A | 0.063 (5) | 0.057 (5) | 0.141 (9) | −0.002 (5) | 0.002 (6) | 0.019 (6) |
O73A | 0.103 (5) | 0.078 (4) | 0.151 (6) | 0.013 (4) | −0.001 (4) | −0.013 (4) |
C74A | 0.088 (6) | 0.110 (7) | 0.119 (8) | 0.009 (5) | −0.024 (6) | 0.028 (6) |
C8A | 0.060 (4) | 0.035 (3) | 0.065 (5) | 0.002 (3) | 0.007 (4) | −0.001 (3) |
C9A | 0.078 (5) | 0.045 (4) | 0.059 (5) | 0.005 (4) | 0.007 (4) | −0.010 (3) |
C10A | 0.082 (5) | 0.051 (4) | 0.058 (4) | −0.004 (4) | 0.014 (4) | 0.002 (3) |
C11A | 0.095 (6) | 0.041 (4) | 0.066 (5) | −0.005 (4) | −0.004 (4) | −0.005 (3) |
O111 | 0.108 (4) | 0.047 (3) | 0.075 (3) | −0.007 (3) | −0.006 (3) | −0.009 (3) |
C112 | 0.137 (8) | 0.071 (6) | 0.073 (6) | −0.024 (6) | 0.008 (6) | −0.029 (5) |
O113 | 0.209 (8) | 0.099 (5) | 0.086 (5) | 0.001 (5) | −0.042 (5) | −0.022 (4) |
C114 | 0.159 (9) | 0.086 (7) | 0.104 (7) | −0.023 (7) | 0.018 (7) | −0.031 (5) |
C12A | 0.065 (4) | 0.050 (4) | 0.062 (5) | −0.006 (3) | −0.004 (4) | −0.003 (3) |
C13A | 0.081 (5) | 0.038 (4) | 0.061 (4) | 0.002 (4) | 0.005 (4) | −0.003 (3) |
C14A | 0.060 (4) | 0.045 (4) | 0.064 (5) | −0.002 (3) | −0.002 (4) | −0.004 (3) |
C15A | 0.072 (5) | 0.065 (5) | 0.065 (5) | 0.006 (4) | −0.003 (4) | −0.001 (4) |
C16A | 0.116 (7) | 0.055 (5) | 0.077 (5) | 0.000 (5) | −0.014 (5) | −0.009 (4) |
C17A | 0.076 (5) | 0.050 (4) | 0.075 (5) | 0.007 (4) | −0.003 (4) | 0.000 (4) |
C18A | 0.082 (5) | 0.041 (4) | 0.070 (5) | 0.001 (4) | −0.005 (4) | 0.003 (3) |
C19A | 0.104 (6) | 0.077 (5) | 0.072 (5) | −0.018 (5) | 0.007 (5) | −0.009 (4) |
C20A | 0.086 (5) | 0.077 (5) | 0.118 (6) | −0.011 (5) | 0.018 (5) | 0.010 (5) |
C21A | 0.081 (5) | 0.068 (5) | 0.090 (5) | 0.005 (4) | 0.017 (4) | 0.023 (4) |
C22A | 0.102 (6) | 0.128 (6) | 0.108 (5) | −0.020 (5) | 0.021 (5) | 0.025 (5) |
C23A | 0.148 (10) | 0.149 (9) | 0.149 (9) | 0.009 (8) | 0.008 (8) | −0.004 (8) |
C24A | 0.225 (12) | 0.217 (11) | 0.185 (11) | 0.008 (8) | 0.044 (9) | −0.011 (9) |
C25A | 0.238 (10) | 0.196 (11) | 0.188 (11) | 0.011 (9) | 0.038 (8) | 0.001 (8) |
C26A | 0.233 (9) | 0.203 (13) | 0.231 (13) | 0.017 (8) | 0.001 (9) | 0.018 (10) |
C27A | 0.255 (12) | 0.222 (13) | 0.247 (13) | −0.002 (10) | −0.003 (9) | −0.011 (9) |
C23D | 0.090 (9) | 0.065 (8) | 0.069 (7) | 0.000 (7) | 0.013 (7) | −0.001 (6) |
C24D | 0.104 (10) | 0.086 (9) | 0.090 (7) | 0.003 (8) | 0.036 (7) | −0.007 (6) |
C25D | 0.105 (9) | 0.077 (8) | 0.068 (7) | 0.000 (7) | 0.009 (7) | −0.005 (6) |
C26D | 0.108 (10) | 0.123 (10) | 0.109 (10) | 0.020 (8) | 0.029 (8) | 0.014 (8) |
C27D | 0.096 (9) | 0.105 (10) | 0.070 (8) | 0.010 (7) | 0.011 (7) | 0.008 (7) |
C28A | 0.137 (8) | 0.102 (7) | 0.136 (8) | 0.020 (7) | 0.056 (7) | 0.035 (6) |
C29A | 0.087 (6) | 0.053 (5) | 0.133 (7) | 0.003 (4) | −0.029 (6) | −0.007 (5) |
C30A | 0.082 (5) | 0.063 (4) | 0.065 (5) | −0.001 (4) | 0.001 (4) | −0.019 (4) |
C1B | 0.109 (6) | 0.061 (5) | 0.072 (5) | −0.010 (5) | 0.000 (5) | −0.012 (4) |
C2B | 0.104 (6) | 0.071 (5) | 0.078 (5) | −0.006 (5) | 0.002 (5) | −0.018 (4) |
C3B | 0.077 (5) | 0.052 (4) | 0.082 (5) | −0.008 (4) | −0.008 (4) | −0.021 (4) |
O31B | 0.095 (4) | 0.064 (3) | 0.098 (4) | 0.001 (3) | −0.010 (3) | −0.031 (3) |
C32B | 0.109 (8) | 0.067 (6) | 0.107 (8) | −0.001 (6) | 0.018 (6) | −0.012 (6) |
O33B | 0.156 (7) | 0.087 (5) | 0.128 (6) | 0.034 (5) | 0.001 (5) | −0.006 (5) |
C34B | 0.172 (10) | 0.071 (6) | 0.170 (10) | −0.001 (7) | 0.035 (9) | −0.043 (7) |
C4B | 0.076 (5) | 0.046 (4) | 0.086 (5) | −0.008 (4) | −0.020 (5) | −0.011 (4) |
C5B | 0.053 (4) | 0.058 (4) | 0.065 (5) | 0.003 (4) | −0.003 (4) | −0.008 (4) |
C6B | 0.074 (5) | 0.058 (5) | 0.093 (6) | −0.013 (4) | −0.012 (5) | −0.001 (4) |
C7B | 0.056 (4) | 0.053 (4) | 0.098 (6) | −0.008 (4) | −0.001 (4) | 0.000 (4) |
O71B | 0.062 (3) | 0.065 (3) | 0.095 (4) | 0.002 (3) | 0.017 (3) | −0.004 (3) |
C72B | 0.064 (5) | 0.062 (5) | 0.118 (8) | 0.006 (5) | −0.007 (6) | −0.026 (5) |
O73B | 0.113 (5) | 0.085 (4) | 0.144 (6) | 0.036 (4) | 0.009 (5) | 0.002 (4) |
C74B | 0.093 (6) | 0.108 (7) | 0.148 (9) | 0.016 (6) | 0.041 (7) | −0.038 (7) |
C8B | 0.074 (5) | 0.037 (4) | 0.074 (5) | 0.012 (3) | 0.012 (4) | 0.010 (3) |
C9B | 0.068 (5) | 0.052 (4) | 0.065 (5) | 0.000 (4) | −0.003 (4) | 0.001 (3) |
C10B | 0.063 (4) | 0.055 (4) | 0.055 (4) | 0.004 (4) | 0.000 (4) | 0.002 (3) |
C11B | 0.074 (5) | 0.050 (4) | 0.056 (4) | 0.000 (4) | −0.001 (4) | −0.003 (3) |
O115 | 0.106 (4) | 0.052 (3) | 0.065 (3) | −0.008 (3) | −0.011 (3) | 0.012 (2) |
C116 | 0.108 (7) | 0.092 (7) | 0.079 (7) | −0.006 (6) | −0.015 (6) | 0.043 (6) |
O117 | 0.174 (7) | 0.124 (6) | 0.090 (5) | 0.013 (5) | 0.043 (5) | 0.014 (4) |
C118 | 0.149 (9) | 0.102 (8) | 0.130 (8) | −0.021 (7) | 0.011 (8) | 0.055 (6) |
C12B | 0.072 (4) | 0.043 (4) | 0.070 (5) | −0.004 (4) | 0.005 (4) | 0.007 (3) |
C13B | 0.059 (4) | 0.047 (4) | 0.060 (4) | 0.001 (3) | 0.005 (4) | −0.010 (3) |
C14B | 0.062 (4) | 0.050 (4) | 0.061 (5) | 0.002 (4) | 0.000 (4) | −0.003 (3) |
C15B | 0.088 (6) | 0.071 (5) | 0.067 (5) | −0.005 (4) | 0.014 (5) | 0.002 (4) |
C16B | 0.092 (6) | 0.071 (5) | 0.075 (5) | 0.008 (5) | 0.001 (5) | −0.006 (4) |
C17B | 0.075 (5) | 0.066 (5) | 0.073 (5) | 0.007 (4) | 0.008 (4) | −0.005 (4) |
C18B | 0.085 (5) | 0.051 (4) | 0.074 (5) | −0.011 (4) | 0.006 (4) | −0.001 (4) |
C19B | 0.092 (5) | 0.077 (5) | 0.065 (5) | 0.009 (5) | −0.020 (4) | 0.012 (4) |
C20B | 0.075 (5) | 0.085 (6) | 0.100 (6) | −0.013 (5) | −0.003 (4) | −0.014 (5) |
C21B | 0.090 (5) | 0.069 (5) | 0.096 (5) | −0.017 (4) | 0.002 (4) | −0.033 (4) |
C22B | 0.134 (8) | 0.139 (8) | 0.094 (5) | −0.029 (6) | −0.002 (5) | −0.024 (6) |
C23B | 0.162 (8) | 0.164 (8) | 0.131 (7) | 0.000 (6) | −0.006 (6) | −0.012 (6) |
C24B | 0.153 (12) | 0.172 (12) | 0.136 (10) | 0.005 (9) | −0.002 (8) | −0.010 (9) |
C25B | 0.164 (12) | 0.174 (13) | 0.170 (12) | 0.002 (8) | −0.003 (8) | 0.012 (9) |
C26B | 0.196 (16) | 0.195 (13) | 0.183 (14) | −0.006 (10) | 0.000 (9) | 0.027 (10) |
C27B | 0.144 (12) | 0.140 (14) | 0.137 (13) | 0.010 (9) | −0.028 (9) | −0.004 (9) |
C24C | 0.163 (10) | 0.195 (9) | 0.143 (9) | 0.020 (8) | −0.011 (7) | −0.012 (8) |
C25C | 0.194 (10) | 0.178 (10) | 0.170 (10) | 0.000 (8) | −0.026 (8) | −0.005 (8) |
C26C | 0.223 (11) | 0.214 (12) | 0.166 (11) | 0.013 (9) | −0.031 (8) | 0.028 (9) |
C27C | 0.248 (12) | 0.240 (12) | 0.272 (14) | −0.033 (9) | −0.002 (9) | 0.015 (9) |
C28B | 0.092 (6) | 0.078 (6) | 0.119 (7) | −0.013 (5) | −0.021 (6) | −0.031 (5) |
C29B | 0.126 (7) | 0.048 (4) | 0.095 (6) | −0.010 (5) | 0.006 (5) | 0.001 (4) |
C30B | 0.079 (5) | 0.043 (4) | 0.072 (5) | −0.002 (3) | −0.010 (4) | 0.010 (3) |
Geometric parameters (Å, º) top
C1A—C2A | 1.501 (9) | C30A—H30C | 0.9840 |
C1A—C10A | 1.510 (10) | C1B—C10B | 1.525 (10) |
C1A—H1A1 | 0.9700 | C1B—C2B | 1.586 (10) |
C1A—H1A2 | 0.9700 | C1B—H1B1 | 0.9700 |
C2A—C3A | 1.551 (11) | C1B—H1B2 | 0.9700 |
C2A—H2A1 | 0.9700 | C2B—C3B | 1.480 (10) |
C2A—H2A2 | 0.9700 | C2B—H2B1 | 0.9700 |
C3A—O31A | 1.428 (8) | C2B—H2B2 | 0.9700 |
C3A—C4A | 1.484 (11) | C3B—O31B | 1.453 (8) |
C3A—H3A | 0.9800 | C3B—C4B | 1.570 (11) |
O31A—C32A | 1.370 (12) | C3B—H3B | 0.9800 |
C32A—O33A | 1.137 (11) | O31B—C32B | 1.336 (11) |
C32A—C34A | 1.513 (13) | C32B—O33B | 1.217 (11) |
C34A—H34A | 0.9785 | C32B—C34B | 1.526 (13) |
C34A—H34B | 0.9872 | C34B—H34D | 0.9772 |
C34A—H34C | 0.9823 | C34B—H34E | 0.9875 |
C4A—C28A | 1.523 (11) | C34B—H34F | 0.9834 |
C4A—C29A | 1.536 (10) | C4B—C29B | 1.531 (10) |
C4A—C5A | 1.562 (9) | C4B—C28B | 1.540 (10) |
C5A—C10A | 1.344 (10) | C4B—C5B | 1.556 (9) |
C5A—C6A | 1.500 (10) | C5B—C10B | 1.322 (9) |
C6A—C7A | 1.535 (9) | C5B—C6B | 1.492 (10) |
C6A—H6A | 0.9700 | C6B—C7B | 1.527 (9) |
C6A—H6B | 0.9700 | C6B—H6C | 0.9700 |
C7A—O71A | 1.463 (8) | C6B—H6D | 0.9700 |
C7A—C8A | 1.510 (9) | C7B—O71B | 1.452 (9) |
C7A—H7A | 0.9800 | C7B—C8B | 1.517 (9) |
O71A—C72A | 1.354 (9) | C7B—H7B | 0.9800 |
C72A—O73A | 1.200 (11) | O71B—C72B | 1.329 (9) |
C72A—C74A | 1.504 (13) | C72B—O73B | 1.182 (10) |
C74A—H74A | 0.9872 | C72B—C74B | 1.440 (12) |
C74A—H74B | 0.9749 | C74B—H74D | 0.9874 |
C74A—H74C | 0.9794 | C74B—H74E | 0.9755 |
C8A—C14A | 1.549 (9) | C74B—H74F | 0.9786 |
C8A—C9A | 1.547 (9) | C8B—C14B | 1.535 (9) |
C8A—H8A | 0.9800 | C8B—C9B | 1.589 (10) |
C9A—C19A | 1.546 (10) | C8B—H8B | 0.9800 |
C9A—C10A | 1.567 (9) | C9B—C10B | 1.526 (9) |
C9A—C11A | 1.563 (10) | C9B—C11B | 1.552 (10) |
C11A—O111 | 1.464 (7) | C9B—C19B | 1.576 (9) |
C11A—C12A | 1.515 (10) | C11B—O115 | 1.475 (8) |
C11A—H11A | 0.9800 | C11B—C12B | 1.548 (9) |
O111—C112 | 1.335 (10) | C11B—H11E | 0.9800 |
C112—O113 | 1.216 (11) | O115—C116 | 1.352 (10) |
C112—C114 | 1.520 (12) | C116—O117 | 1.179 (11) |
C114—H11B | 0.9873 | C116—C118 | 1.520 (13) |
C114—H11C | 0.9801 | C118—H11F | 0.9822 |
C114—H11D | 0.9830 | C118—H11G | 0.9871 |
C12A—C13A | 1.499 (9) | C118—H11H | 0.9814 |
C12A—H12A | 0.9700 | C12B—C13B | 1.517 (9) |
C12A—H12B | 0.9700 | C12B—H12C | 0.9700 |
C13A—C18A | 1.564 (8) | C12B—H12D | 0.9700 |
C13A—C14A | 1.567 (9) | C13B—C18B | 1.531 (9) |
C13A—C17A | 1.573 (9) | C13B—C17B | 1.545 (9) |
C14A—C15A | 1.521 (10) | C13B—C14B | 1.586 (9) |
C14A—C30A | 1.577 (9) | C14B—C30B | 1.528 (9) |
C15A—C16A | 1.534 (10) | C14B—C15B | 1.536 (9) |
C15A—H15A | 0.9700 | C15B—C16B | 1.533 (11) |
C15A—H15B | 0.9700 | C15B—H15C | 0.9700 |
C16A—C17A | 1.559 (10) | C15B—H15D | 0.9700 |
C16A—H16A | 0.9700 | C16B—C17B | 1.558 (10) |
C16A—H16B | 0.9700 | C16B—H16C | 0.9699 |
C17A—C21A | 1.542 (10) | C16B—H16D | 0.9700 |
C17A—H17A | 0.9800 | C17B—C21B | 1.549 (10) |
C18A—H18A | 0.9841 | C17B—H17B | 0.9800 |
C18A—H18B | 0.9828 | C18B—H18D | 0.9846 |
C18A—H18C | 0.9826 | C18B—H18E | 0.9823 |
C19A—H191 | 0.9835 | C18B—H18F | 0.9822 |
C19A—H192 | 0.9749 | C19B—H194 | 0.9839 |
C19A—H193 | 0.9837 | C19B—H195 | 0.9748 |
C20A—C21A | 1.493 (11) | C19B—H196 | 0.9834 |
C20A—H20A | 0.9764 | C20B—C21B | 1.519 (11) |
C20A—H20B | 0.9812 | C20B—H20D | 0.9812 |
C20A—H20C | 0.9772 | C20B—H20E | 0.9818 |
C21A—C22A | 1.525 (9) | C20B—H20F | 0.9761 |
C21A—H21A | 0.9800 | C21B—C22B | 1.514 (11) |
C22A—C23D | 1.5328 | C21B—H21B | 0.9800 |
C22A—C23A | 1.5342 | C22B—C23B | 1.521 (5) |
C22A—H22A | 1.0073 | C22B—H22E | 0.9700 |
C22A—H22B | 1.0207 | C22B—H22F | 0.9700 |
C22A—H22C | 1.0205 | C23B—C24C | 1.5262 |
C22A—H22D | 1.0106 | C23B—C24B | 1.5408 |
C23A—C24A | 1.5287 | C23B—H23E | 1.0199 |
C23A—H23A | 0.9897 | C23B—H23F | 1.0094 |
C23A—H23B | 0.9968 | C23B—H23G | 1.0139 |
C24A—C25A | 1.5420 | C23B—H23H | 1.0131 |
C24A—H24A | 0.9928 | C24B—C25B | 1.4961 |
C24A—H24B | 0.9985 | C24B—H24E | 0.9700 |
C25A—C26A | 1.5029 | C24B—H24F | 0.9700 |
C25A—C27A | 1.5284 | C25B—C27B | 1.5033 |
C25A—H25A | 1.0051 | C25B—C26B | 1.5197 |
C26A—H26A | 0.9730 | C25B—H25B | 0.9800 |
C26A—H26B | 0.9836 | C26B—H26G | 0.9761 |
C26A—H26C | 0.9717 | C26B—H26H | 0.9843 |
C27A—H27A | 0.9919 | C26B—H26I | 0.9830 |
C27A—H27B | 0.9794 | C27B—H27G | 0.9820 |
C27A—H27C | 0.9659 | C27B—H27H | 0.9805 |
C23D—C24D | 1.5319 | C27B—H27I | 0.9763 |
C23D—H23C | 0.9700 | C27B—H25C | 0.9883 |
C23D—H23D | 0.9700 | C24C—C25C | 1.5519 |
C24D—C25D | 1.5430 | C24C—H24G | 0.9700 |
C24D—H24C | 0.9700 | C24C—H24H | 0.9700 |
C24D—H24D | 0.9700 | C25C—C27C | 1.5657 |
C25D—C26D | 1.5222 | C25C—C26C | 1.5671 |
C25D—C27D | 1.5330 | C25C—H25C | 0.9800 |
C25D—H25D | 0.9800 | C26C—H26J | 0.9756 |
C26D—H26D | 0.9600 | C26C—H26K | 0.9849 |
C26D—H26E | 0.9600 | C26C—H26L | 0.9778 |
C26D—H26F | 0.9600 | C27C—H27J | 0.9803 |
C27D—H27D | 0.9600 | C27C—H27K | 0.9855 |
C27D—H27E | 0.9600 | C27C—H27L | 0.9758 |
C27D—H27F | 0.9600 | C28B—H284 | 0.9857 |
C28A—H281 | 0.9745 | C28B—H285 | 0.9786 |
C28A—H282 | 0.9858 | C28B—H286 | 0.9744 |
C28A—H283 | 0.9790 | C29B—H294 | 0.9854 |
C29A—H291 | 0.9841 | C29B—H295 | 0.9862 |
C29A—H292 | 0.9869 | C29B—H296 | 0.9743 |
C29A—H293 | 0.9744 | C30B—H30D | 0.9823 |
C30A—H30A | 0.9824 | C30B—H30E | 0.9822 |
C30A—H30B | 0.9828 | C30B—H30F | 0.9846 |
| | | |
C2A—C1A—C10A | 115.1 (7) | H30A—C30A—H30C | 109.8 |
C2A—C1A—H1A1 | 108.5 | H30B—C30A—H30C | 109.2 |
C10A—C1A—H1A1 | 108.5 | C10B—C1B—C2B | 112.6 (7) |
C2A—C1A—H1A2 | 108.5 | C10B—C1B—H1B1 | 109.0 |
C10A—C1A—H1A2 | 108.5 | C2B—C1B—H1B1 | 109.3 |
H1A1—C1A—H1A2 | 107.5 | C10B—C1B—H1B2 | 109.4 |
C1A—C2A—C3A | 108.9 (6) | C2B—C1B—H1B2 | 108.7 |
C1A—C2A—H2A1 | 109.9 | H1B1—C1B—H1B2 | 107.8 |
C3A—C2A—H2A1 | 109.9 | C3B—C2B—C1B | 108.3 (6) |
C1A—C2A—H2A2 | 109.9 | C3B—C2B—H2B1 | 109.9 |
C3A—C2A—H2A2 | 109.9 | C1B—C2B—H2B1 | 109.9 |
H2A1—C2A—H2A2 | 108.3 | C3B—C2B—H2B2 | 109.9 |
O31A—C3A—C4A | 110.4 (7) | C1B—C2B—H2B2 | 110.3 |
O31A—C3A—C2A | 109.0 (6) | H2B1—C2B—H2B2 | 108.5 |
C4A—C3A—C2A | 113.6 (7) | O31B—C3B—C2B | 106.9 (6) |
O31A—C3A—H3A | 107.9 | O31B—C3B—C4B | 108.1 (6) |
C4A—C3A—H3A | 107.9 | C2B—C3B—C4B | 113.7 (7) |
C2A—C3A—H3A | 107.9 | O31B—C3B—H3B | 109.6 |
C32A—O31A—C3A | 118.3 (7) | C2B—C3B—H3B | 109.4 |
O33A—C32A—O31A | 125.8 (9) | C4B—C3B—H3B | 109.0 |
O33A—C32A—C34A | 125.2 (11) | C32B—O31B—C3B | 118.6 (7) |
O31A—C32A—C34A | 108.6 (10) | O33B—C32B—O31B | 124.7 (9) |
C32A—C34A—H34A | 108.1 | O33B—C32B—C34B | 125.2 (11) |
C32A—C34A—H34B | 112.8 | O31B—C32B—C34B | 110.1 (10) |
H34A—C34A—H34B | 109.9 | C32B—C34B—H34D | 105.7 |
C32A—C34A—H34C | 107.1 | C32B—C34B—H34E | 109.0 |
H34A—C34A—H34C | 109.3 | H34D—C34B—H34E | 109.6 |
H34B—C34A—H34C | 109.5 | C32B—C34B—H34F | 113.2 |
C3A—C4A—C28A | 110.9 (7) | H34D—C34B—H34F | 109.5 |
C3A—C4A—C29A | 107.8 (7) | H34E—C34B—H34F | 109.7 |
C28A—C4A—C29A | 108.6 (7) | C29B—C4B—C28B | 110.8 (7) |
C3A—C4A—C5A | 110.4 (6) | C29B—C4B—C5B | 111.4 (6) |
C28A—C4A—C5A | 108.6 (7) | C28B—C4B—C5B | 108.5 (6) |
C29A—C4A—C5A | 110.5 (6) | C29B—C4B—C3B | 108.0 (7) |
C10A—C5A—C6A | 123.4 (6) | C28B—C4B—C3B | 110.4 (6) |
C10A—C5A—C4A | 122.8 (7) | C5B—C4B—C3B | 107.6 (6) |
C6A—C5A—C4A | 113.8 (6) | C10B—C5B—C6B | 122.9 (6) |
C5A—C6A—C7A | 112.9 (6) | C10B—C5B—C4B | 125.1 (7) |
C5A—C6A—H6A | 109.0 | C6B—C5B—C4B | 112.0 (6) |
C7A—C6A—H6A | 109.0 | C5B—C6B—C7B | 115.3 (6) |
C5A—C6A—H6B | 109.0 | C5B—C6B—H6C | 109.0 |
C7A—C6A—H6B | 109.0 | C7B—C6B—H6C | 109.5 |
H6A—C6A—H6B | 107.8 | C5B—C6B—H6D | 107.7 |
O71A—C7A—C8A | 112.5 (6) | C7B—C6B—H6D | 107.7 |
O71A—C7A—C6A | 104.1 (6) | H6C—C6B—H6D | 107.5 |
C8A—C7A—C6A | 116.5 (6) | O71B—C7B—C8B | 112.7 (6) |
O71A—C7A—H7A | 107.8 | O71B—C7B—C6B | 107.3 (6) |
C8A—C7A—H7A | 107.8 | C8B—C7B—C6B | 114.9 (6) |
C6A—C7A—H7A | 107.8 | O71B—C7B—H7B | 107.1 |
C72A—O71A—C7A | 117.4 (7) | C8B—C7B—H7B | 107.3 |
O73A—C72A—O71A | 121.9 (10) | C6B—C7B—H7B | 107.1 |
O73A—C72A—C74A | 127.2 (9) | C72B—O71B—C7B | 117.5 (7) |
O71A—C72A—C74A | 110.9 (9) | O73B—C72B—O71B | 124.5 (9) |
C72A—C74A—H74A | 110.4 | O73B—C72B—C74B | 122.8 (9) |
C72A—C74A—H74B | 108.3 | O71B—C72B—C74B | 112.7 (9) |
H74A—C74A—H74B | 109.4 | C72B—C74B—H74D | 111.1 |
C72A—C74A—H74C | 109.8 | C72B—C74B—H74E | 105.5 |
H74A—C74A—H74C | 109.9 | H74D—C74B—H74E | 109.5 |
H74B—C74A—H74C | 109.0 | C72B—C74B—H74F | 111.8 |
C7A—C8A—C14A | 118.7 (6) | H74D—C74B—H74F | 109.8 |
C7A—C8A—C9A | 107.0 (5) | H74E—C74B—H74F | 108.9 |
C14A—C8A—C9A | 114.1 (5) | C7B—C8B—C14B | 118.7 (6) |
C7A—C8A—H8A | 105.3 | C7B—C8B—C9B | 107.8 (6) |
C14A—C8A—H8A | 105.3 | C14B—C8B—C9B | 113.3 (5) |
C9A—C8A—H8A | 105.3 | C7B—C8B—H8B | 105.5 |
C8A—C9A—C19A | 109.9 (6) | C14B—C8B—H8B | 105.0 |
C8A—C9A—C10A | 112.1 (5) | C9B—C8B—H8B | 105.3 |
C19A—C9A—C10A | 104.3 (6) | C10B—C9B—C11B | 113.5 (6) |
C8A—C9A—C11A | 111.3 (6) | C10B—C9B—C19B | 104.4 (6) |
C19A—C9A—C11A | 108.2 (5) | C11B—C9B—C19B | 107.1 (5) |
C10A—C9A—C11A | 110.8 (6) | C10B—C9B—C8B | 112.3 (5) |
C5A—C10A—C1A | 121.9 (6) | C11B—C9B—C8B | 111.2 (6) |
C5A—C10A—C9A | 120.9 (7) | C19B—C9B—C8B | 107.9 (5) |
C1A—C10A—C9A | 116.7 (6) | C5B—C10B—C1B | 122.7 (6) |
O111—C11A—C12A | 106.6 (5) | C5B—C10B—C9B | 122.8 (6) |
O111—C11A—C9A | 108.2 (6) | C1B—C10B—C9B | 114.4 (6) |
C12A—C11A—C9A | 117.9 (6) | O115—C11B—C12B | 106.6 (5) |
O111—C11A—H11A | 107.9 | O115—C11B—C9B | 110.4 (6) |
C12A—C11A—H11A | 107.9 | C12B—C11B—C9B | 117.6 (5) |
C9A—C11A—H11A | 107.9 | O115—C11B—H11E | 107.2 |
C112—O111—C11A | 118.3 (6) | C12B—C11B—H11E | 107.1 |
O113—C112—O111 | 124.2 (8) | C9B—C11B—H11E | 107.5 |
O113—C112—C114 | 125.1 (9) | C116—O115—C11B | 116.6 (7) |
O111—C112—C114 | 110.6 (9) | O117—C116—O115 | 125.8 (9) |
C112—C114—H11B | 108.6 | O117—C116—C118 | 127.2 (9) |
C112—C114—H11C | 110.9 | O115—C116—C118 | 107.0 (10) |
H11B—C114—H11C | 109.7 | C116—C118—H11F | 109.8 |
C112—C114—H11D | 108.4 | C116—C118—H11G | 108.3 |
H11B—C114—H11D | 109.7 | H11F—C118—H11G | 109.7 |
H11C—C114—H11D | 109.6 | C116—C118—H11H | 109.8 |
C13A—C12A—C11A | 113.8 (6) | H11F—C118—H11H | 109.5 |
C13A—C12A—H12A | 108.8 | H11G—C118—H11H | 109.8 |
C11A—C12A—H12A | 108.8 | C13B—C12B—C11B | 112.5 (5) |
C13A—C12A—H12B | 108.8 | C13B—C12B—H12C | 109.7 |
C11A—C12A—H12B | 108.8 | C11B—C12B—H12C | 109.0 |
H12A—C12A—H12B | 107.7 | C13B—C12B—H12D | 109.0 |
C12A—C13A—C18A | 111.6 (5) | C11B—C12B—H12D | 108.8 |
C12A—C13A—C14A | 107.9 (5) | H12C—C12B—H12D | 107.7 |
C18A—C13A—C14A | 110.9 (6) | C12B—C13B—C18B | 111.6 (5) |
C12A—C13A—C17A | 118.3 (6) | C12B—C13B—C17B | 116.8 (5) |
C18A—C13A—C17A | 106.2 (5) | C18B—C13B—C17B | 107.4 (5) |
C14A—C13A—C17A | 101.5 (5) | C12B—C13B—C14B | 107.2 (5) |
C15A—C14A—C8A | 116.9 (6) | C18B—C13B—C14B | 112.2 (5) |
C15A—C14A—C30A | 107.1 (5) | C17B—C13B—C14B | 101.3 (5) |
C8A—C14A—C30A | 111.7 (5) | C30B—C14B—C8B | 112.6 (5) |
C15A—C14A—C13A | 100.2 (5) | C30B—C14B—C15B | 104.2 (6) |
C8A—C14A—C13A | 109.3 (5) | C8B—C14B—C15B | 117.9 (6) |
C30A—C14A—C13A | 111.1 (5) | C30B—C14B—C13B | 111.1 (5) |
C14A—C15A—C16A | 105.8 (6) | C8B—C14B—C13B | 109.8 (5) |
C14A—C15A—H15A | 110.6 | C15B—C14B—C13B | 100.5 (5) |
C16A—C15A—H15A | 110.6 | C16B—C15B—C14B | 105.3 (6) |
C14A—C15A—H15B | 110.6 | C16B—C15B—H15C | 111.8 |
C16A—C15A—H15B | 110.6 | C14B—C15B—H15C | 111.4 |
H15A—C15A—H15B | 108.7 | C16B—C15B—H15D | 110.1 |
C15A—C16A—C17A | 106.8 (6) | C14B—C15B—H15D | 109.6 |
C15A—C16A—H16A | 110.4 | H15C—C15B—H15D | 108.6 |
C17A—C16A—H16A | 110.4 | C15B—C16B—C17B | 106.9 (6) |
C15A—C16A—H16B | 110.4 | C15B—C16B—H16C | 109.4 |
C17A—C16A—H16B | 110.4 | C17B—C16B—H16C | 111.1 |
H16A—C16A—H16B | 108.6 | C15B—C16B—H16D | 110.3 |
C21A—C17A—C16A | 112.7 (6) | C17B—C16B—H16D | 110.4 |
C21A—C17A—C13A | 119.6 (6) | H16C—C16B—H16D | 108.7 |
C16A—C17A—C13A | 102.3 (6) | C13B—C17B—C21B | 118.8 (6) |
C21A—C17A—H17A | 107.2 | C13B—C17B—C16B | 103.7 (6) |
C16A—C17A—H17A | 107.2 | C21B—C17B—C16B | 113.2 (6) |
C13A—C17A—H17A | 107.2 | C13B—C17B—H17B | 106.8 |
C13A—C18A—H18A | 108.7 | C21B—C17B—H17B | 106.8 |
C13A—C18A—H18B | 110.4 | C16B—C17B—H17B | 106.8 |
H18A—C18A—H18B | 109.2 | C13B—C18B—H18D | 109.7 |
C13A—C18A—H18C | 108.8 | C13B—C18B—H18E | 108.8 |
H18A—C18A—H18C | 109.8 | H18D—C18B—H18E | 109.2 |
H18B—C18A—H18C | 109.9 | C13B—C18B—H18F | 109.4 |
C9A—C19A—H191 | 109.6 | H18D—C18B—H18F | 109.8 |
C9A—C19A—H192 | 109.1 | H18E—C18B—H18F | 109.9 |
H191—C19A—H192 | 108.9 | C9B—C19B—H194 | 110.3 |
C9A—C19A—H193 | 109.8 | C9B—C19B—H195 | 107.4 |
H191—C19A—H193 | 109.7 | H194—C19B—H195 | 108.9 |
H192—C19A—H193 | 109.7 | C9B—C19B—H196 | 110.8 |
C21A—C20A—H20A | 109.5 | H194—C19B—H196 | 109.7 |
C21A—C20A—H20B | 110.2 | H195—C19B—H196 | 109.7 |
H20A—C20A—H20B | 110.3 | C21B—C20B—H20D | 111.1 |
C21A—C20A—H20C | 108.4 | C21B—C20B—H20E | 109.6 |
H20A—C20A—H20C | 109.6 | H20D—C20B—H20E | 109.9 |
H20B—C20A—H20C | 108.8 | C21B—C20B—H20F | 108.1 |
C20A—C21A—C22A | 109.1 (6) | H20D—C20B—H20F | 109.3 |
C20A—C21A—C17A | 114.6 (6) | H20E—C20B—H20F | 108.8 |
C22A—C21A—C17A | 110.9 (6) | C22B—C21B—C20B | 112.0 (7) |
C20A—C21A—H21A | 107.3 | C22B—C21B—C17B | 113.3 (7) |
C22A—C21A—H21A | 107.3 | C20B—C21B—C17B | 114.0 (6) |
C17A—C21A—H21A | 107.3 | C22B—C21B—H21B | 104.2 |
C21A—C22A—C23D | 120.6 (4) | C20B—C21B—H21B | 106.7 |
C21A—C22A—C23A | 120.3 (4) | C17B—C21B—H21B | 105.7 |
C23D—C22A—C23A | 109.1 | C21B—C22B—C23B | 114.7 (7) |
C21A—C22A—H22A | 107.1 | C21B—C22B—H22E | 109.7 |
C23A—C22A—H22A | 109.1 | C23B—C22B—H22E | 106.1 |
C21A—C22A—H22B | 106.8 | C21B—C22B—H22F | 109.6 |
C23A—C22A—H22B | 105.2 | C23B—C22B—H22F | 108.8 |
H22A—C22A—H22B | 107.8 | H22E—C22B—H22F | 107.6 |
C21A—C22A—H22C | 104.0 | C22B—C23B—C24C | 119.3 (4) |
C23D—C22A—H22C | 101.6 | C22B—C23B—C24B | 108.9 (4) |
C21A—C22A—H22D | 108.0 | C22B—C23B—H23F | 106.0 |
H22A—C22A—H22D | 109.6 | H23E—C23B—H23F | 109.4 |
H22C—C22A—H22D | 106.3 | C22B—C23B—H23G | 109.8 |
C24A—C23A—C22A | 114.9 | C23B—C24B—H24E | 109.8 |
C22A—C23A—H23A | 110.1 | C25B—C24B—H24F | 138.9 |
H22D—C23A—H23A | 107.6 | C23B—C24B—H24F | 103.5 |
C22A—C23A—H23B | 106.1 | H24E—C24B—H24F | 104.1 |
H23A—C23A—H23B | 107.9 | C25B—C24B—H24G | 100.3 |
C23A—C24A—C25A | 109.7 | H24E—C24B—H24G | 110.9 |
C23A—C24A—H24A | 117.4 | H24F—C24B—H24H | 104.5 |
C25A—C24A—H24A | 117.5 | H24G—C24B—H24H | 120.0 |
C25A—C24A—H24B | 103.3 | C24B—C25B—C27B | 115.4 |
H24A—C24A—H24B | 107.3 | C24B—C25B—C26B | 114.6 |
C23A—C24A—H24D | 111.6 | C27B—C25B—C26B | 114.9 |
C26A—C25A—C27A | 113.4 | H25B—C25B—H26I | 117.2 |
C26A—C25A—C24A | 112.3 | C24B—C25B—H25C | 112.5 |
C27A—C25A—C24A | 109.0 | H24E—C25B—H25C | 117.9 |
C25A—C26A—H26A | 124.9 | H24E—C25B—H26K | 112.3 |
C25A—C26A—H26B | 122.8 | C25B—C26B—H26H | 116.6 |
H26A—C26A—H26B | 108.7 | H26G—C26B—H26H | 109.5 |
H26A—C26A—H26C | 110.9 | H26G—C26B—H26I | 109.7 |
H26B—C26A—H26C | 110.0 | H26H—C26B—H26I | 109.2 |
H27A—C27A—H27B | 109.4 | C25B—C26B—H27J | 108.3 |
H25A—C27A—H27C | 107.3 | H26G—C26B—H27J | 117.4 |
H27A—C27A—H27C | 110.1 | H26J—C26B—H27L | 117.1 |
H27B—C27A—H27C | 109.7 | H27G—C27B—H27H | 109.5 |
C24D—C23D—C22A | 109.7 | H27G—C27B—H27I | 109.7 |
C24D—C23D—H23C | 107.8 | H27H—C27B—H27I | 108.8 |
C22A—C23D—H23C | 105.9 | C23B—C24C—C25C | 114.4 |
H22A—C23D—H23C | 113.7 | C23B—C24C—H24E | 121.1 |
C24D—C23D—H23D | 111.8 | C25C—C24C—H24E | 106.1 |
C22A—C23D—H23D | 113.5 | C23B—C24C—H24G | 109.1 |
H23C—C23D—H23D | 107.9 | C25C—C24C—H24G | 105.8 |
C23D—C24D—C25D | 110.7 | C23B—C24C—H24H | 106.7 |
C23D—C24D—H24C | 112.3 | C25C—C24C—H24H | 112.3 |
C25D—C24D—H24C | 107.0 | H24G—C24C—H24H | 108.4 |
C23D—C24D—H24D | 108.4 | C24C—C25C—C27C | 108.2 |
C25D—C24D—H24D | 110.3 | C24C—C25C—C26C | 107.2 |
H24C—C24D—H24D | 108.2 | C27C—C25C—C26C | 103.4 |
C26D—C25D—C27D | 111.0 | C24C—C25C—H25C | 108.5 |
C26D—C25D—C24D | 110.0 | C27C—C25C—H25C | 111.1 |
C27D—C25D—C24D | 109.5 | C26C—C25C—H25C | 118.0 |
C26D—C25D—H25D | 107.1 | H25B—C25C—H25C | 130.6 |
C27D—C25D—H25D | 108.2 | C25C—C26C—H26J | 114.5 |
C24D—C25D—H25D | 111.1 | H26J—C26C—H26K | 109.2 |
C25D—C26D—H26D | 113.1 | H26J—C26C—H26L | 109.1 |
C25D—C26D—H26E | 102.8 | H26K—C26C—H26L | 109.8 |
H26D—C26D—H26E | 109.5 | H26I—C27C—H27J | 109.1 |
C25D—C26D—H26F | 112.3 | C25C—C27C—H27K | 120.8 |
H26D—C26D—H26F | 109.5 | H27J—C27C—H27K | 109.2 |
H26E—C26D—H26F | 109.5 | C25C—C27C—H27L | 108.0 |
C25D—C27D—H27D | 110.0 | H26I—C27C—H27L | 102.3 |
C25D—C27D—H27E | 103.8 | H27J—C27C—H27L | 109.2 |
H27D—C27D—H27E | 109.5 | H27K—C27C—H27L | 109.8 |
C25D—C27D—H27F | 114.4 | C4B—C28B—H284 | 107.4 |
H27D—C27D—H27F | 109.5 | C4B—C28B—H285 | 111.8 |
H27E—C27D—H27F | 109.5 | H284—C28B—H285 | 109.6 |
C4A—C28A—H281 | 110.4 | C4B—C28B—H286 | 109.6 |
C4A—C28A—H282 | 110.7 | H284—C28B—H286 | 109.4 |
H281—C28A—H282 | 109.3 | H285—C28B—H286 | 109.1 |
C4A—C28A—H283 | 107.6 | C4B—C29B—H294 | 109.8 |
H281—C28A—H283 | 109.1 | C4B—C29B—H295 | 110.9 |
H282—C28A—H283 | 109.7 | H294—C29B—H295 | 109.8 |
C4A—C29A—H291 | 111.7 | C4B—C29B—H296 | 107.5 |
C4A—C29A—H292 | 108.5 | H294—C29B—H296 | 109.4 |
H291—C29A—H292 | 109.8 | H295—C29B—H296 | 109.4 |
C4A—C29A—H293 | 108.0 | C14B—C30B—H30D | 109.1 |
H291—C29A—H293 | 109.4 | C14B—C30B—H30E | 107.9 |
H292—C29A—H293 | 109.5 | H30D—C30B—H30E | 109.9 |
C14A—C30A—H30A | 109.6 | C14B—C30B—H30F | 111.0 |
C14A—C30A—H30B | 109.3 | H30D—C30B—H30F | 109.8 |
H30A—C30A—H30B | 109.9 | H30E—C30B—H30F | 109.2 |
C14A—C30A—H30C | 108.9 | | |
| | | |
C10A—C1A—C2A—C3A | −42.7 (10) | C23D—C24D—C25D—C27D | −164.2 |
C1A—C2A—C3A—O31A | −175.2 (7) | C10B—C1B—C2B—C3B | −44.7 (9) |
C1A—C2A—C3A—C4A | 61.4 (10) | C1B—C2B—C3B—O31B | −176.8 (7) |
C4A—C3A—O31A—C32A | −122.8 (8) | C1B—C2B—C3B—C4B | 63.9 (8) |
C2A—C3A—O31A—C32A | 111.9 (9) | C2B—C3B—O31B—C32B | 124.5 (8) |
C3A—O31A—C32A—O33A | 6.8 (16) | C4B—C3B—O31B—C32B | −112.7 (8) |
C3A—O31A—C32A—C34A | 179.3 (8) | C3B—O31B—C32B—O33B | 0.9 (14) |
O31A—C3A—C4A—C28A | −48.7 (9) | C3B—O31B—C32B—C34B | −177.4 (7) |
C2A—C3A—C4A—C28A | 73.9 (9) | O31B—C3B—C4B—C29B | 71.8 (7) |
O31A—C3A—C4A—C29A | 70.0 (8) | C2B—C3B—C4B—C29B | −169.6 (6) |
C2A—C3A—C4A—C29A | −167.3 (6) | O31B—C3B—C4B—C28B | −49.5 (8) |
O31A—C3A—C4A—C5A | −169.2 (6) | C2B—C3B—C4B—C28B | 69.1 (8) |
C2A—C3A—C4A—C5A | −46.5 (9) | O31B—C3B—C4B—C5B | −167.7 (6) |
C3A—C4A—C5A—C10A | 15.6 (10) | C2B—C3B—C4B—C5B | −49.2 (8) |
C28A—C4A—C5A—C10A | −106.2 (9) | C29B—C4B—C5B—C10B | 135.3 (8) |
C29A—C4A—C5A—C10A | 134.8 (7) | C28B—C4B—C5B—C10B | −102.5 (8) |
C3A—C4A—C5A—C6A | −162.6 (7) | C3B—C4B—C5B—C10B | 17.0 (9) |
C28A—C4A—C5A—C6A | 75.6 (9) | C29B—C4B—C5B—C6B | −45.8 (8) |
C29A—C4A—C5A—C6A | −43.4 (9) | C28B—C4B—C5B—C6B | 76.4 (8) |
C10A—C5A—C6A—C7A | 12.3 (10) | C3B—C4B—C5B—C6B | −164.1 (6) |
C4A—C5A—C6A—C7A | −169.5 (6) | C10B—C5B—C6B—C7B | 9.0 (10) |
C5A—C6A—C7A—O71A | −162.4 (6) | C4B—C5B—C6B—C7B | −169.9 (6) |
C5A—C6A—C7A—C8A | −37.9 (9) | C5B—C6B—C7B—O71B | −161.8 (6) |
C8A—C7A—O71A—C72A | 86.6 (7) | C5B—C6B—C7B—C8B | −35.6 (10) |
C6A—C7A—O71A—C72A | −146.4 (6) | C8B—C7B—O71B—C72B | 85.5 (7) |
C7A—O71A—C72A—O73A | 3.6 (11) | C6B—C7B—O71B—C72B | −147.0 (6) |
C7A—O71A—C72A—C74A | −177.3 (6) | C7B—O71B—C72B—O73B | −0.6 (12) |
O71A—C7A—C8A—C14A | 46.8 (7) | C7B—O71B—C72B—C74B | −179.0 (7) |
C6A—C7A—C8A—C14A | −73.3 (9) | O71B—C7B—C8B—C14B | 47.1 (8) |
O71A—C7A—C8A—C9A | 177.7 (5) | C6B—C7B—C8B—C14B | −76.3 (9) |
C6A—C7A—C8A—C9A | 57.6 (8) | O71B—C7B—C8B—C9B | 177.7 (5) |
C7A—C8A—C9A—C19A | 64.3 (7) | C6B—C7B—C8B—C9B | 54.3 (8) |
C14A—C8A—C9A—C19A | −162.3 (5) | C7B—C8B—C9B—C10B | −48.4 (7) |
C7A—C8A—C9A—C10A | −51.3 (7) | C14B—C8B—C9B—C10B | 85.1 (7) |
C14A—C8A—C9A—C10A | 82.1 (7) | C7B—C8B—C9B—C11B | −176.8 (5) |
C7A—C8A—C9A—C11A | −175.9 (5) | C14B—C8B—C9B—C11B | −43.3 (7) |
C14A—C8A—C9A—C11A | −42.5 (7) | C7B—C8B—C9B—C19B | 66.1 (7) |
C6A—C5A—C10A—C1A | 179.0 (7) | C14B—C8B—C9B—C19B | −160.4 (5) |
C4A—C5A—C10A—C1A | 0.9 (11) | C6B—C5B—C10B—C1B | 179.3 (7) |
C6A—C5A—C10A—C9A | −9.9 (10) | C4B—C5B—C10B—C1B | −2.0 (10) |
C4A—C5A—C10A—C9A | 172.0 (6) | C6B—C5B—C10B—C9B | −5.3 (10) |
C2A—C1A—C10A—C5A | 14.0 (11) | C4B—C5B—C10B—C9B | 173.5 (6) |
C2A—C1A—C10A—C9A | −157.4 (7) | C2B—C1B—C10B—C5B | 15.3 (10) |
C8A—C9A—C10A—C5A | 30.5 (9) | C2B—C1B—C10B—C9B | −160.5 (6) |
C19A—C9A—C10A—C5A | −88.4 (8) | C11B—C9B—C10B—C5B | 153.1 (6) |
C11A—C9A—C10A—C5A | 155.4 (6) | C19B—C9B—C10B—C5B | −90.7 (7) |
C8A—C9A—C10A—C1A | −158.0 (6) | C8B—C9B—C10B—C5B | 25.9 (9) |
C19A—C9A—C10A—C1A | 83.1 (8) | C11B—C9B—C10B—C1B | −31.1 (8) |
C11A—C9A—C10A—C1A | −33.0 (8) | C19B—C9B—C10B—C1B | 85.1 (7) |
C8A—C9A—C11A—O111 | −85.2 (6) | C8B—C9B—C10B—C1B | −158.3 (6) |
C19A—C9A—C11A—O111 | 35.6 (7) | C10B—C9B—C11B—O115 | 147.3 (5) |
C10A—C9A—C11A—O111 | 149.4 (5) | C19B—C9B—C11B—O115 | 32.6 (7) |
C8A—C9A—C11A—C12A | 35.7 (8) | C8B—C9B—C11B—O115 | −85.0 (6) |
C19A—C9A—C11A—C12A | 156.5 (6) | C10B—C9B—C11B—C12B | −90.2 (7) |
C10A—C9A—C11A—C12A | −89.7 (7) | C19B—C9B—C11B—C12B | 155.2 (6) |
C12A—C11A—O111—C112 | 116.4 (7) | C8B—C9B—C11B—C12B | 37.6 (7) |
C9A—C11A—O111—C112 | −115.9 (7) | C12B—C11B—O115—C116 | 116.0 (7) |
C11A—O111—C112—O113 | 1.6 (13) | C9B—C11B—O115—C116 | −115.2 (7) |
C11A—O111—C112—C114 | −177.7 (7) | C11B—O115—C116—O117 | 4.1 (13) |
O111—C11A—C12A—C13A | 76.6 (7) | C11B—O115—C116—C118 | −174.2 (7) |
C9A—C11A—C12A—C13A | −45.1 (8) | O115—C11B—C12B—C13B | 76.8 (6) |
C11A—C12A—C13A—C18A | −64.8 (7) | C9B—C11B—C12B—C13B | −47.7 (7) |
C11A—C12A—C13A—C14A | 57.3 (7) | C11B—C12B—C13B—C18B | −64.7 (7) |
C11A—C12A—C13A—C17A | 171.6 (5) | C11B—C12B—C13B—C17B | 171.3 (5) |
C7A—C8A—C14A—C15A | −61.7 (8) | C11B—C12B—C13B—C14B | 58.6 (6) |
C9A—C8A—C14A—C15A | 170.7 (6) | C7B—C8B—C14B—C30B | 62.0 (8) |
C7A—C8A—C14A—C30A | 62.1 (8) | C9B—C8B—C14B—C30B | −66.0 (7) |
C9A—C8A—C14A—C30A | −65.5 (7) | C7B—C8B—C14B—C15B | −59.5 (8) |
C7A—C8A—C14A—C13A | −174.5 (5) | C9B—C8B—C14B—C15B | 172.5 (6) |
C9A—C8A—C14A—C13A | 57.9 (7) | C7B—C8B—C14B—C13B | −173.7 (6) |
C12A—C13A—C14A—C15A | 173.2 (5) | C9B—C8B—C14B—C13B | 58.3 (7) |
C18A—C13A—C14A—C15A | −64.3 (7) | C12B—C13B—C14B—C30B | 60.1 (7) |
C17A—C13A—C14A—C15A | 48.1 (6) | C18B—C13B—C14B—C30B | −177.0 (6) |
C12A—C13A—C14A—C8A | −63.5 (6) | C17B—C13B—C14B—C30B | −62.7 (7) |
C18A—C13A—C14A—C8A | 59.0 (7) | C12B—C13B—C14B—C8B | −65.1 (6) |
C17A—C13A—C14A—C8A | 171.5 (5) | C18B—C13B—C14B—C8B | 57.8 (7) |
C12A—C13A—C14A—C30A | 60.3 (7) | C17B—C13B—C14B—C8B | 172.0 (5) |
C18A—C13A—C14A—C30A | −177.2 (5) | C12B—C13B—C14B—C15B | 170.0 (5) |
C17A—C13A—C14A—C30A | −64.7 (7) | C18B—C13B—C14B—C15B | −67.2 (7) |
C8A—C14A—C15A—C16A | −157.1 (5) | C17B—C13B—C14B—C15B | 47.1 (6) |
C30A—C14A—C15A—C16A | 76.7 (7) | C30B—C14B—C15B—C16B | 77.1 (7) |
C13A—C14A—C15A—C16A | −39.3 (7) | C8B—C14B—C15B—C16B | −157.2 (6) |
C14A—C15A—C16A—C17A | 15.5 (7) | C13B—C14B—C15B—C16B | −38.0 (7) |
C15A—C16A—C17A—C21A | 144.4 (6) | C14B—C15B—C16B—C17B | 15.0 (8) |
C15A—C16A—C17A—C13A | 14.8 (7) | C12B—C13B—C17B—C21B | 79.4 (8) |
C12A—C13A—C17A—C21A | 78.4 (8) | C18B—C13B—C17B—C21B | −46.8 (8) |
C18A—C13A—C17A—C21A | −47.8 (8) | C14B—C13B—C17B—C21B | −164.6 (6) |
C14A—C13A—C17A—C21A | −163.8 (6) | C12B—C13B—C17B—C16B | −154.0 (6) |
C12A—C13A—C17A—C16A | −156.3 (6) | C18B—C13B—C17B—C16B | 79.8 (7) |
C18A—C13A—C17A—C16A | 77.4 (6) | C14B—C13B—C17B—C16B | −38.0 (6) |
C14A—C13A—C17A—C16A | −38.6 (6) | C15B—C16B—C17B—C13B | 15.0 (7) |
C16A—C17A—C21A—C20A | −177.9 (6) | C15B—C16B—C17B—C21B | 145.1 (7) |
C13A—C17A—C21A—C20A | −57.7 (9) | C13B—C17B—C21B—C22B | 172.8 (6) |
C16A—C17A—C21A—C22A | 58.0 (8) | C16B—C17B—C21B—C22B | 50.9 (9) |
C13A—C17A—C21A—C22A | 178.1 (6) | C13B—C17B—C21B—C20B | −57.6 (9) |
C20A—C21A—C22A—C23D | 77.9 (6) | C16B—C17B—C21B—C20B | −179.6 (7) |
C17A—C21A—C22A—C23D | −154.9 (4) | C20B—C21B—C22B—C23B | −62.8 (10) |
C20A—C21A—C22A—C23A | −63.7 (7) | C17B—C21B—C22B—C23B | 67.8 (10) |
C17A—C21A—C22A—C23A | 63.5 (6) | C21B—C22B—C23B—C24C | 161.9 (5) |
C21A—C22A—C23A—C24A | 166.1 (5) | C21B—C22B—C23B—C24B | 170.2 (6) |
C23D—C22A—C23A—C24A | 20.5 | C22B—C23B—C24B—C25B | −168.8 (5) |
C22A—C23A—C24A—C25A | 171.2 | C24C—C23B—C24B—C25B | −23.3 |
C23A—C24A—C25A—C26A | 126.2 | C23B—C24B—C25B—C27B | 37.3 |
C23A—C24A—C25A—C27A | −107.3 | C23B—C24B—C25B—C26B | −99.5 |
C21A—C22A—C23D—C24D | 173.9 (4) | C22B—C23B—C24C—C25C | 165.4 (6) |
C23A—C22A—C23D—C24D | −40.6 | C24B—C23B—C24C—C25C | 127.5 |
C22A—C23D—C24D—C25D | −177.7 | C23B—C24C—C25C—C27C | −66.8 |
C23D—C24D—C25D—C26D | 73.6 | C23B—C24C—C25C—C26C | −177.7 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2A—H2A1···O117i | 0.97 | 2.62 | 3.534 (14) | 158 |
C21A—H21A···O73Aii | 0.98 | 2.73 | 3.476 (10) | 133 |
C29A—H292···O73B | 0.99 | 2.57 | 3.553 (11) | 176 |
C2B—H2B2···O113iii | 0.97 | 2.58 | 3.429 (14) | 146 |
C34B—H34F···O117iv | 0.98 | 2.65 | 3.630 (13) | 171 |
C74B—H74F···O33Av | 0.98 | 2.82 | 3.792 (13) | 176 |
C21B—H21B···O73Bv | 0.98 | 2.68 | 3.410 (11) | 131 |
C29B—H295···O73A | 0.99 | 2.60 | 3.558 (12) | 163 |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z+2; (iii) x+1, y, z; (iv) −x+2, y−1/2, −z+3/2; (v) x+1/2, −y+5/2, −z+2. |
Crystal data top
C36H58O6 | Dx = 1.104 Mg m−3 |
Mr = 586.82 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 5203 reflections |
a = 9.0756 (7) Å | θ = 2.3–27.8° |
b = 14.9566 (17) Å | µ = 0.07 mm−1 |
c = 26.008 (2) Å | T = 295 K |
V = 3530.3 (6) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.3 × 0.1 mm |
F(000) = 1288 | |
Data collection top
Kuma KM-4 CCD four-circle diffractometer | 2109 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 27.0°, θmin = 2.6° |
/w scan | h = −11→11 |
21091 measured reflections | k = −18→19 |
4264 independent reflections | l = −33→33 |
Refinement top
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)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.070P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.89 | (Δ/σ)max = 0.004 |
4264 reflections | Δρmax = 0.15 e Å−3 |
412 parameters | Δρmin = −0.14 e Å−3 |
38 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | |
Crystal data top
C36H58O6 | V = 3530.3 (6) Å3 |
Mr = 586.82 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.0756 (7) Å | µ = 0.07 mm−1 |
b = 14.9566 (17) Å | T = 295 K |
c = 26.008 (2) Å | 0.35 × 0.3 × 0.1 mm |
Data collection top
Kuma KM-4 CCD four-circle diffractometer | 2109 reflections with I > 2σ(I) |
21091 measured reflections | Rint = 0.047 |
4264 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.051 | 38 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 0.89 | Δρmax = 0.15 e Å−3 |
4264 reflections | Δρmin = −0.14 e Å−3 |
412 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Special details top
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. |
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 > 2sigma(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 | Occ. (<1) |
C1 | 0.2153 (4) | 0.8570 (3) | 0.11401 (14) | 0.0758 (12) | |
H1 | 0.2010 | 0.9173 | 0.1211 | 0.091* | |
C2 | 0.1428 (5) | 0.8198 (3) | 0.06656 (14) | 0.0859 (13) | |
H2A | 0.0419 | 0.8410 | 0.0651 | 0.103* | |
H2B | 0.1939 | 0.8424 | 0.0365 | 0.103* | |
C3 | 0.1427 (4) | 0.7194 (3) | 0.06496 (13) | 0.0683 (11) | |
H3 | 0.1220 | 0.6992 | 0.0298 | 0.082* | |
O31 | 0.0251 (3) | 0.6905 (2) | 0.09884 (8) | 0.0793 (9) | |
C32 | −0.0805 (5) | 0.6383 (3) | 0.08100 (15) | 0.0754 (12) | |
O33 | −0.0826 (4) | 0.6071 (3) | 0.03884 (11) | 0.1136 (12) | |
C34 | −0.1969 (4) | 0.6240 (5) | 0.12088 (17) | 0.1118 (19) | |
H34A | −0.2669 | 0.5808 | 0.1086 | 0.168* | |
H34B | −0.2464 | 0.6795 | 0.1276 | 0.168* | |
H34C | −0.1523 | 0.6024 | 0.1520 | 0.168* | |
C4 | 0.2900 (4) | 0.6787 (3) | 0.08340 (12) | 0.0599 (10) | |
C5 | 0.3267 (4) | 0.7116 (3) | 0.13827 (11) | 0.0522 (9) | |
H5 | 0.4333 | 0.7037 | 0.1423 | 0.063* | |
C6 | 0.2557 (4) | 0.6589 (2) | 0.18251 (10) | 0.0547 (9) | |
H6A | 0.1600 | 0.6371 | 0.1716 | 0.066* | |
H6B | 0.3167 | 0.6076 | 0.1906 | 0.066* | |
C7 | 0.2371 (3) | 0.7157 (3) | 0.23025 (11) | 0.0520 (9) | |
H7 | 0.1452 | 0.7491 | 0.2256 | 0.062* | |
O71 | 0.2155 (2) | 0.65928 (17) | 0.27506 (7) | 0.0565 (6) | |
C72 | 0.0815 (4) | 0.6229 (3) | 0.28236 (13) | 0.0585 (10) | |
O73 | −0.0206 (3) | 0.6336 (2) | 0.25395 (10) | 0.0773 (8) | |
C74 | 0.0796 (4) | 0.5665 (3) | 0.32978 (13) | 0.0765 (12) | |
H74A | −0.0170 | 0.5418 | 0.3345 | 0.115* | |
H74B | 0.1047 | 0.6027 | 0.3590 | 0.115* | |
H74C | 0.1499 | 0.5190 | 0.3263 | 0.115* | |
C8 | 0.3559 (3) | 0.7852 (3) | 0.24299 (11) | 0.0508 (9) | |
H8 | 0.3120 | 0.8220 | 0.2702 | 0.061* | |
C9 | 0.3700 (4) | 0.8515 (2) | 0.19481 (12) | 0.0539 (9) | |
C10 | 0.2978 (4) | 0.8108 (3) | 0.14660 (12) | 0.0550 (9) | |
C11 | 0.5359 (4) | 0.8649 (3) | 0.18168 (11) | 0.0558 (9) | |
H11 | 0.5713 | 0.8107 | 0.1645 | 0.067* | |
O111 | 0.5435 (3) | 0.93894 (18) | 0.14465 (8) | 0.0669 (7) | |
C112 | 0.6279 (6) | 0.9259 (4) | 0.10266 (16) | 0.0886 (15) | |
O113 | 0.7043 (5) | 0.8628 (4) | 0.09583 (14) | 0.1324 (15) | |
C114 | 0.6108 (7) | 1.0049 (4) | 0.06690 (16) | 0.119 (2) | |
H11A | 0.6680 | 0.9950 | 0.0364 | 0.178* | |
H11B | 0.6448 | 1.0581 | 0.0838 | 0.178* | |
H11C | 0.5089 | 1.0117 | 0.0578 | 0.178* | |
C12 | 0.6399 (4) | 0.8858 (3) | 0.22576 (12) | 0.0581 (9) | |
H12A | 0.6386 | 0.9498 | 0.2318 | 0.070* | |
H12B | 0.7392 | 0.8697 | 0.2155 | 0.070* | |
C13 | 0.6032 (4) | 0.8373 (2) | 0.27685 (11) | 0.0497 (9) | |
C14 | 0.5056 (3) | 0.7534 (2) | 0.26601 (11) | 0.0477 (8) | |
C15 | 0.4984 (4) | 0.7111 (3) | 0.32013 (12) | 0.0609 (10) | |
H15A | 0.4755 | 0.6479 | 0.3181 | 0.073* | |
H15B | 0.4245 | 0.7405 | 0.3411 | 0.073* | |
C16 | 0.6548 (4) | 0.7261 (3) | 0.34236 (13) | 0.0657 (11) | |
H16A | 0.7091 | 0.6703 | 0.3428 | 0.079* | |
H16B | 0.6486 | 0.7487 | 0.3773 | 0.079* | |
C17 | 0.7341 (4) | 0.7956 (3) | 0.30698 (12) | 0.0532 (9) | |
H17 | 0.7933 | 0.7617 | 0.2822 | 0.064* | |
C18 | 0.5283 (4) | 0.9035 (3) | 0.31471 (12) | 0.0626 (10) | |
H18A | 0.5053 | 0.8730 | 0.3462 | 0.094* | |
H18B | 0.4393 | 0.9261 | 0.2996 | 0.094* | |
H18C | 0.5941 | 0.9522 | 0.3217 | 0.094* | |
C19 | 0.2992 (4) | 0.9419 (3) | 0.20781 (14) | 0.0682 (11) | |
H19A | 0.1977 | 0.9330 | 0.2168 | 0.102* | |
H19B | 0.3054 | 0.9807 | 0.1785 | 0.102* | |
H19C | 0.3503 | 0.9685 | 0.2363 | 0.102* | |
C20 | 0.9134 (4) | 0.9267 (3) | 0.30168 (14) | 0.0748 (12) | |
H20A | 0.9750 | 0.9654 | 0.3218 | 0.112* | |
H20B | 0.8386 | 0.9614 | 0.2849 | 0.112* | |
H20C | 0.9721 | 0.8965 | 0.2763 | 0.112* | |
C21 | 0.8410 (4) | 0.8578 (3) | 0.33678 (12) | 0.0602 (10) | |
H21 | 0.7841 | 0.8899 | 0.3629 | 0.072* | |
C22 | 0.9606 (4) | 0.8035 (3) | 0.36413 (13) | 0.0708 (11) | |
H22A | 0.9146 | 0.7532 | 0.3813 | 0.085* | |
H22B | 1.0277 | 0.7797 | 0.3385 | 0.085* | |
C23 | 1.0486 (5) | 0.8559 (4) | 0.40319 (15) | 0.0909 (14) | |
H23A | 0.9825 | 0.8775 | 0.4297 | 0.109* | |
H23B | 1.0919 | 0.9076 | 0.3864 | 0.109* | |
C24 | 1.1706 (5) | 0.8012 (4) | 0.42815 (16) | 0.1028 (17) | |
H24A | 1.2205 | 0.7702 | 0.3992 | 0.123* | 0.560 (12) |
H24B | 1.1300 | 0.7538 | 0.4518 | 0.123* | 0.560 (12) |
H24C | 1.2530 | 0.8053 | 0.4035 | 0.123* | 0.440 (12) |
H24D | 1.1405 | 0.7369 | 0.4301 | 0.123* | 0.440 (12) |
C25 | 1.2817 (14) | 0.8648 (12) | 0.4608 (5) | 0.144 (7) | 0.560 (12) |
H25 | 1.3051 | 0.9190 | 0.4413 | 0.173* | 0.560 (12) |
C26 | 1.4210 (15) | 0.8081 (12) | 0.4687 (6) | 0.182 (6) | 0.560 (12) |
H26A | 1.3935 | 0.7491 | 0.4795 | 0.236* | 0.560 (12) |
H26B | 1.4821 | 0.8353 | 0.4944 | 0.236* | 0.560 (12) |
H26C | 1.4745 | 0.8045 | 0.4369 | 0.236* | 0.560 (12) |
C27 | 1.2157 (14) | 0.8877 (12) | 0.5091 (5) | 0.174 (6) | 0.560 (12) |
H27A | 1.2892 | 0.9127 | 0.5315 | 0.226* | 0.560 (12) |
H27B | 1.1748 | 0.8351 | 0.5246 | 0.226* | 0.560 (12) |
H27C | 1.1390 | 0.9309 | 0.5036 | 0.226* | 0.560 (12) |
C25A | 1.2337 (18) | 0.8351 (11) | 0.4775 (6) | 0.113 (7) | 0.440 (12) |
H25A | 1.1546 | 0.8583 | 0.4995 | 0.135* | 0.440 (12) |
C26A | 1.315 (2) | 0.7629 (15) | 0.5051 (7) | 0.180 (9) | 0.440 (12) |
H26D | 1.3525 | 0.7857 | 0.5371 | 0.234* | 0.440 (12) |
H26E | 1.3961 | 0.7428 | 0.4842 | 0.234* | 0.440 (12) |
H26F | 1.2500 | 0.7138 | 0.5117 | 0.234* | 0.440 (12) |
C27A | 1.340 (2) | 0.9115 (14) | 0.4631 (8) | 0.167 (9) | 0.440 (12) |
H27D | 1.2862 | 0.9664 | 0.4597 | 0.217* | 0.440 (12) |
H27E | 1.3878 | 0.8978 | 0.4311 | 0.217* | 0.440 (12) |
H27F | 1.4134 | 0.9180 | 0.4895 | 0.217* | 0.440 (12) |
C28 | 0.4096 (4) | 0.7108 (3) | 0.04603 (13) | 0.0851 (14) | |
H28A | 0.3866 | 0.6906 | 0.0119 | 0.128* | |
H28B | 0.5032 | 0.6870 | 0.0563 | 0.128* | |
H28C | 0.4137 | 0.7749 | 0.0464 | 0.128* | |
C29 | 0.2834 (4) | 0.5772 (3) | 0.08092 (13) | 0.0737 (12) | |
H29A | 0.2595 | 0.5588 | 0.0465 | 0.111* | |
H29B | 0.2093 | 0.5558 | 0.1042 | 0.111* | |
H29C | 0.3774 | 0.5528 | 0.0905 | 0.111* | |
C30 | 0.5873 (4) | 0.6822 (3) | 0.23346 (12) | 0.0596 (10) | |
H30A | 0.5169 | 0.6478 | 0.2143 | 0.089* | |
H30B | 0.6421 | 0.6433 | 0.2558 | 0.089* | |
H30C | 0.6537 | 0.7114 | 0.2101 | 0.089* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.088 (3) | 0.064 (3) | 0.075 (2) | 0.015 (3) | −0.019 (2) | −0.001 (2) |
C2 | 0.103 (3) | 0.083 (4) | 0.072 (2) | 0.009 (3) | −0.026 (2) | 0.007 (3) |
C3 | 0.074 (2) | 0.079 (3) | 0.0518 (19) | 0.002 (3) | −0.0054 (19) | −0.001 (2) |
O31 | 0.0639 (15) | 0.111 (3) | 0.0635 (14) | 0.0087 (18) | −0.0042 (13) | −0.0127 (17) |
C32 | 0.074 (3) | 0.080 (3) | 0.073 (3) | 0.006 (3) | −0.015 (2) | 0.003 (3) |
O33 | 0.134 (3) | 0.132 (3) | 0.0748 (18) | −0.043 (2) | −0.0038 (19) | −0.011 (2) |
C34 | 0.060 (2) | 0.165 (6) | 0.110 (3) | 0.010 (3) | 0.007 (2) | −0.001 (4) |
C4 | 0.062 (2) | 0.064 (3) | 0.0543 (19) | 0.005 (2) | 0.0011 (17) | 0.0029 (19) |
C5 | 0.0507 (18) | 0.053 (3) | 0.0525 (18) | 0.0066 (19) | −0.0019 (15) | 0.0027 (18) |
C6 | 0.061 (2) | 0.052 (2) | 0.0517 (17) | −0.0009 (19) | −0.0041 (16) | −0.0009 (18) |
C7 | 0.0483 (18) | 0.051 (2) | 0.0562 (18) | −0.0018 (19) | −0.0002 (16) | 0.0035 (19) |
O71 | 0.0472 (12) | 0.0669 (18) | 0.0554 (12) | −0.0088 (13) | 0.0039 (10) | 0.0055 (13) |
C72 | 0.054 (2) | 0.056 (3) | 0.066 (2) | −0.007 (2) | 0.0086 (18) | −0.009 (2) |
O73 | 0.0483 (13) | 0.093 (2) | 0.0905 (16) | −0.0009 (16) | −0.0019 (13) | 0.0012 (17) |
C74 | 0.076 (2) | 0.080 (3) | 0.073 (2) | −0.010 (3) | 0.020 (2) | 0.005 (2) |
C8 | 0.0524 (18) | 0.051 (2) | 0.0489 (17) | 0.0109 (19) | 0.0051 (15) | −0.0012 (17) |
C9 | 0.060 (2) | 0.043 (2) | 0.0581 (19) | 0.007 (2) | 0.0022 (16) | 0.0072 (19) |
C10 | 0.0565 (19) | 0.054 (3) | 0.0546 (18) | 0.005 (2) | −0.0051 (17) | 0.0055 (19) |
C11 | 0.066 (2) | 0.048 (2) | 0.0533 (18) | 0.000 (2) | 0.0045 (16) | 0.0108 (18) |
O111 | 0.0787 (16) | 0.0613 (18) | 0.0608 (14) | −0.0041 (15) | 0.0007 (13) | 0.0190 (14) |
C112 | 0.100 (4) | 0.100 (4) | 0.065 (3) | −0.022 (3) | 0.007 (3) | 0.018 (3) |
O113 | 0.146 (3) | 0.133 (4) | 0.118 (3) | 0.021 (3) | 0.068 (2) | 0.028 (3) |
C114 | 0.163 (5) | 0.120 (5) | 0.074 (3) | −0.036 (4) | −0.009 (3) | 0.040 (3) |
C12 | 0.0561 (19) | 0.058 (3) | 0.0603 (19) | −0.001 (2) | 0.0027 (17) | 0.009 (2) |
C13 | 0.0534 (18) | 0.045 (2) | 0.0501 (17) | 0.0021 (18) | 0.0044 (15) | 0.0001 (17) |
C14 | 0.0525 (18) | 0.042 (2) | 0.0485 (17) | 0.0001 (17) | 0.0040 (15) | 0.0034 (16) |
C15 | 0.067 (2) | 0.059 (3) | 0.0568 (19) | −0.009 (2) | −0.0041 (17) | 0.0088 (19) |
C16 | 0.073 (2) | 0.065 (3) | 0.0587 (19) | −0.002 (2) | −0.0098 (19) | 0.009 (2) |
C17 | 0.0555 (19) | 0.050 (2) | 0.0544 (17) | 0.0042 (19) | −0.0018 (16) | −0.0008 (18) |
C18 | 0.065 (2) | 0.055 (3) | 0.068 (2) | 0.006 (2) | −0.0043 (19) | −0.005 (2) |
C19 | 0.074 (2) | 0.048 (3) | 0.082 (2) | 0.011 (2) | −0.012 (2) | 0.005 (2) |
C20 | 0.068 (2) | 0.073 (3) | 0.084 (2) | −0.012 (2) | −0.014 (2) | 0.013 (2) |
C21 | 0.059 (2) | 0.058 (3) | 0.064 (2) | 0.001 (2) | −0.0017 (17) | −0.001 (2) |
C22 | 0.068 (2) | 0.076 (3) | 0.069 (2) | 0.002 (2) | −0.0092 (19) | −0.001 (2) |
C23 | 0.087 (3) | 0.100 (4) | 0.086 (3) | 0.005 (3) | −0.028 (2) | −0.009 (3) |
C24 | 0.081 (3) | 0.145 (5) | 0.082 (3) | 0.026 (3) | −0.020 (2) | −0.003 (3) |
C25 | 0.091 (9) | 0.22 (2) | 0.124 (10) | −0.030 (12) | −0.061 (8) | 0.073 (12) |
C26 | 0.155 (9) | 0.225 (11) | 0.165 (9) | 0.007 (8) | −0.024 (7) | −0.025 (8) |
C27 | 0.174 (9) | 0.194 (10) | 0.152 (8) | 0.035 (8) | −0.012 (7) | −0.075 (8) |
C25A | 0.096 (9) | 0.135 (11) | 0.107 (10) | 0.016 (8) | −0.016 (7) | −0.001 (8) |
C26A | 0.181 (12) | 0.201 (13) | 0.158 (10) | 0.003 (9) | −0.047 (9) | 0.029 (9) |
C27A | 0.181 (13) | 0.164 (12) | 0.156 (11) | −0.029 (9) | −0.052 (9) | 0.008 (9) |
C28 | 0.085 (3) | 0.112 (4) | 0.058 (2) | −0.001 (3) | 0.0072 (19) | 0.005 (3) |
C29 | 0.086 (3) | 0.076 (3) | 0.059 (2) | 0.006 (3) | −0.003 (2) | −0.009 (2) |
C30 | 0.064 (2) | 0.054 (3) | 0.0604 (18) | 0.009 (2) | −0.0033 (17) | 0.001 (2) |
Geometric parameters (Å, º) top
C1—C10 | 1.326 (5) | C15—H15B | 0.9700 |
C1—C2 | 1.505 (5) | C16—C17 | 1.564 (5) |
C1—H1 | 0.9300 | C16—H16A | 0.9700 |
C2—C3 | 1.503 (6) | C16—H16B | 0.9700 |
C2—H2A | 0.9700 | C17—C21 | 1.552 (5) |
C2—H2B | 0.9700 | C17—H17 | 0.9800 |
C3—O31 | 1.450 (4) | C18—H18A | 0.9600 |
C3—C4 | 1.545 (5) | C18—H18B | 0.9600 |
C3—H3 | 0.9800 | C18—H18C | 0.9600 |
O31—C32 | 1.320 (5) | C19—H19A | 0.9600 |
C32—O33 | 1.192 (4) | C19—H19B | 0.9600 |
C32—C34 | 1.496 (5) | C19—H19C | 0.9600 |
C34—H34A | 0.9600 | C20—C21 | 1.525 (5) |
C34—H34B | 0.9600 | C20—H20A | 0.9600 |
C34—H34C | 0.9600 | C20—H20B | 0.9600 |
C4—C29 | 1.522 (6) | C20—H20C | 0.9600 |
C4—C28 | 1.534 (5) | C21—C22 | 1.531 (5) |
C4—C5 | 1.546 (4) | C21—H21 | 0.9800 |
C5—C10 | 1.521 (5) | C22—C23 | 1.511 (5) |
C5—C6 | 1.537 (4) | C22—H22A | 0.9700 |
C5—H5 | 0.9800 | C22—H22B | 0.9700 |
C6—C7 | 1.514 (4) | C23—C24 | 1.522 (6) |
C6—H6A | 0.9700 | C23—H23A | 0.9700 |
C6—H6B | 0.9700 | C23—H23B | 0.9700 |
C7—O71 | 1.453 (4) | C24—C25A | 1.494 (14) |
C7—C8 | 1.534 (5) | C24—C25 | 1.626 (14) |
C7—H7 | 0.9800 | C24—H24A | 0.9946 |
O71—C72 | 1.345 (4) | C24—H24B | 1.0089 |
C72—O73 | 1.196 (4) | C24—H24C | 0.9871 |
C72—C74 | 1.494 (5) | C24—H24D | 1.0010 |
C74—H74A | 0.9600 | C25—C27 | 1.433 (15) |
C74—H74B | 0.9600 | C25—C26 | 1.536 (15) |
C74—H74C | 0.9600 | C25—H25 | 0.9800 |
C8—C14 | 1.559 (4) | C26—H26A | 0.9600 |
C8—C9 | 1.603 (4) | C26—H26B | 0.9600 |
C8—H8 | 0.9800 | C26—H26C | 0.9600 |
C9—C19 | 1.534 (5) | C27—H27A | 0.9600 |
C9—C10 | 1.540 (5) | C27—H27B | 0.9600 |
C9—C11 | 1.557 (5) | C27—H27C | 0.9600 |
C11—O111 | 1.469 (4) | C25A—C26A | 1.493 (16) |
C11—C12 | 1.518 (4) | C25A—C27A | 1.544 (18) |
C11—H11 | 0.9800 | C25A—H25A | 0.9800 |
O111—C112 | 1.348 (5) | C26A—H26D | 0.9600 |
C112—O113 | 1.185 (6) | C26A—H26E | 0.9600 |
C112—C114 | 1.511 (7) | C26A—H26F | 0.9600 |
C114—H11A | 0.9600 | C27A—H27D | 0.9600 |
C114—H11B | 0.9600 | C27A—H27E | 0.9600 |
C114—H11C | 0.9600 | C27A—H27F | 0.9600 |
C12—C13 | 1.550 (4) | C28—H28A | 0.9600 |
C12—H12A | 0.9700 | C28—H28B | 0.9600 |
C12—H12B | 0.9700 | C28—H28C | 0.9600 |
C13—C18 | 1.552 (5) | C29—H29A | 0.9600 |
C13—C17 | 1.554 (4) | C29—H29B | 0.9600 |
C13—C14 | 1.562 (5) | C29—H29C | 0.9600 |
C14—C15 | 1.544 (4) | C30—H30A | 0.9600 |
C14—C30 | 1.549 (5) | C30—H30B | 0.9600 |
C15—C16 | 1.549 (5) | C30—H30C | 0.9600 |
C15—H15A | 0.9700 | | |
| | | |
C10—C1—C2 | 125.4 (4) | C14—C15—C16 | 104.0 (3) |
C10—C1—H1 | 117.3 | C14—C15—H15A | 111.0 |
C2—C1—H1 | 117.3 | C16—C15—H15A | 111.0 |
C3—C2—C1 | 113.1 (3) | C14—C15—H15B | 111.0 |
C3—C2—H2A | 109.0 | C16—C15—H15B | 111.0 |
C1—C2—H2A | 109.0 | H15A—C15—H15B | 109.0 |
C3—C2—H2B | 109.0 | C15—C16—C17 | 107.3 (3) |
C1—C2—H2B | 109.0 | C15—C16—H16A | 110.2 |
H2A—C2—H2B | 107.8 | C17—C16—H16A | 110.2 |
O31—C3—C2 | 106.3 (3) | C15—C16—H16B | 110.2 |
O31—C3—C4 | 109.4 (3) | C17—C16—H16B | 110.2 |
C2—C3—C4 | 112.6 (4) | H16A—C16—H16B | 108.5 |
O31—C3—H3 | 109.5 | C21—C17—C13 | 119.3 (3) |
C2—C3—H3 | 109.5 | C21—C17—C16 | 113.1 (3) |
C4—C3—H3 | 109.5 | C13—C17—C16 | 102.2 (3) |
C32—O31—C3 | 119.8 (3) | C21—C17—H17 | 107.2 |
O33—C32—O31 | 124.6 (4) | C13—C17—H17 | 107.2 |
O33—C32—C34 | 124.7 (5) | C16—C17—H17 | 107.2 |
O31—C32—C34 | 110.7 (4) | C13—C18—H18A | 109.5 |
C32—C34—H34A | 109.5 | C13—C18—H18B | 109.5 |
C32—C34—H34B | 109.5 | H18A—C18—H18B | 109.5 |
H34A—C34—H34B | 109.5 | C13—C18—H18C | 109.5 |
C32—C34—H34C | 109.5 | H18A—C18—H18C | 109.5 |
H34A—C34—H34C | 109.5 | H18B—C18—H18C | 109.5 |
H34B—C34—H34C | 109.5 | C9—C19—H19A | 109.5 |
C29—C4—C28 | 108.2 (3) | C9—C19—H19B | 109.5 |
C29—C4—C3 | 110.2 (3) | H19A—C19—H19B | 109.5 |
C28—C4—C3 | 107.0 (3) | C9—C19—H19C | 109.5 |
C29—C4—C5 | 111.4 (3) | H19A—C19—H19C | 109.5 |
C28—C4—C5 | 109.4 (3) | H19B—C19—H19C | 109.5 |
C3—C4—C5 | 110.4 (3) | C21—C20—H20A | 109.5 |
C10—C5—C6 | 108.7 (3) | C21—C20—H20B | 109.5 |
C10—C5—C4 | 113.9 (3) | H20A—C20—H20B | 109.5 |
C6—C5—C4 | 116.0 (3) | C21—C20—H20C | 109.5 |
C10—C5—H5 | 105.8 | H20A—C20—H20C | 109.5 |
C6—C5—H5 | 105.8 | H20B—C20—H20C | 109.5 |
C4—C5—H5 | 105.8 | C20—C21—C22 | 109.3 (3) |
C7—C6—C5 | 111.9 (3) | C20—C21—C17 | 112.0 (3) |
C7—C6—H6A | 109.2 | C22—C21—C17 | 110.9 (3) |
C5—C6—H6A | 109.2 | C20—C21—H21 | 108.1 |
C7—C6—H6B | 109.2 | C22—C21—H21 | 108.1 |
C5—C6—H6B | 109.2 | C17—C21—H21 | 108.1 |
H6A—C6—H6B | 107.9 | C23—C22—C21 | 114.3 (4) |
O71—C7—C6 | 110.3 (3) | C23—C22—H22A | 108.7 |
O71—C7—C8 | 108.4 (2) | C21—C22—H22A | 108.7 |
C6—C7—C8 | 118.6 (3) | C23—C22—H22B | 108.7 |
O71—C7—H7 | 106.3 | C21—C22—H22B | 108.7 |
C6—C7—H7 | 106.3 | H22A—C22—H22B | 107.6 |
C8—C7—H7 | 106.3 | C22—C23—C24 | 113.1 (4) |
C72—O71—C7 | 118.1 (2) | C22—C23—H23A | 109.0 |
O73—C72—O71 | 124.0 (3) | C24—C23—H23A | 109.0 |
O73—C72—C74 | 125.2 (3) | C22—C23—H23B | 109.0 |
O71—C72—C74 | 110.8 (3) | C24—C23—H23B | 109.0 |
C72—C74—H74A | 109.5 | H23A—C23—H23B | 107.8 |
C72—C74—H74B | 109.5 | C25A—C24—C23 | 117.6 (8) |
H74A—C74—H74B | 109.5 | C23—C24—C25 | 111.1 (6) |
C72—C74—H74C | 109.5 | C23—C24—H24A | 105.0 |
H74A—C74—H74C | 109.5 | C25—C24—H24A | 112.8 |
H74B—C74—H74C | 109.5 | C23—C24—H24B | 111.8 |
C7—C8—C14 | 119.2 (3) | C25—C24—H24B | 108.5 |
C7—C8—C9 | 107.8 (2) | H24A—C24—H24B | 107.6 |
C14—C8—C9 | 114.8 (3) | C25A—C24—H24C | 104.3 |
C7—C8—H8 | 104.4 | C23—C24—H24C | 103.9 |
C14—C8—H8 | 104.4 | C25A—C24—H24D | 112.7 |
C9—C8—H8 | 104.4 | C23—C24—H24D | 109.9 |
C19—C9—C10 | 110.5 (3) | H24C—C24—H24D | 107.5 |
C19—C9—C11 | 109.9 (3) | C27—C25—C26 | 111.1 (11) |
C10—C9—C11 | 106.5 (3) | C27—C25—C24 | 109.8 (12) |
C19—C9—C8 | 109.8 (3) | C26—C25—C24 | 104.8 (11) |
C10—C9—C8 | 111.0 (3) | C27—C25—H25 | 110.3 |
C11—C9—C8 | 109.1 (3) | C26—C25—H25 | 110.3 |
C1—C10—C5 | 121.0 (3) | C24—C25—H25 | 110.3 |
C1—C10—C9 | 123.7 (4) | C26A—C25A—C24 | 110.9 (13) |
C5—C10—C9 | 115.4 (3) | C26A—C25A—C27A | 109.9 (17) |
O111—C11—C12 | 108.1 (3) | C24—C25A—C27A | 106.4 (13) |
O111—C11—C9 | 106.7 (3) | C26A—C25A—H25A | 109.8 |
C12—C11—C9 | 117.6 (3) | C24—C25A—H25A | 109.8 |
O111—C11—H11 | 108.1 | C27A—C25A—H25A | 109.8 |
C12—C11—H11 | 108.1 | C25A—C26A—H26D | 109.5 |
C9—C11—H11 | 108.1 | C25A—C26A—H26E | 109.5 |
C112—O111—C11 | 116.7 (3) | H26D—C26A—H26E | 109.5 |
O113—C112—O111 | 124.7 (5) | C25A—C26A—H26F | 109.5 |
O113—C112—C114 | 126.2 (5) | H26D—C26A—H26F | 109.5 |
O111—C112—C114 | 109.1 (5) | H26E—C26A—H26F | 109.5 |
C112—C114—H11A | 109.5 | C25A—C27A—H27D | 109.5 |
C112—C114—H11B | 109.5 | C25A—C27A—H27E | 109.5 |
H11A—C114—H11B | 109.5 | H27D—C27A—H27E | 109.5 |
C112—C114—H11C | 109.5 | C25A—C27A—H27F | 109.5 |
H11A—C114—H11C | 109.5 | H27D—C27A—H27F | 109.5 |
H11B—C114—H11C | 109.5 | H27E—C27A—H27F | 109.5 |
C11—C12—C13 | 114.6 (3) | C4—C28—H28A | 109.5 |
C11—C12—H12A | 108.6 | C4—C28—H28B | 109.5 |
C13—C12—H12A | 108.6 | H28A—C28—H28B | 109.5 |
C11—C12—H12B | 108.6 | C4—C28—H28C | 109.5 |
C13—C12—H12B | 108.6 | H28A—C28—H28C | 109.5 |
H12A—C12—H12B | 107.6 | H28B—C28—H28C | 109.5 |
C12—C13—C18 | 109.8 (3) | C4—C29—H29A | 109.5 |
C12—C13—C17 | 117.1 (3) | C4—C29—H29B | 109.5 |
C18—C13—C17 | 105.7 (2) | H29A—C29—H29B | 109.5 |
C12—C13—C14 | 110.1 (2) | C4—C29—H29C | 109.5 |
C18—C13—C14 | 112.3 (3) | H29A—C29—H29C | 109.5 |
C17—C13—C14 | 101.6 (3) | H29B—C29—H29C | 109.5 |
C15—C14—C30 | 103.7 (3) | C14—C30—H30A | 109.5 |
C15—C14—C8 | 116.0 (3) | C14—C30—H30B | 109.5 |
C30—C14—C8 | 114.7 (3) | H30A—C30—H30B | 109.5 |
C15—C14—C13 | 100.9 (2) | C14—C30—H30C | 109.5 |
C30—C14—C13 | 112.3 (3) | H30A—C30—H30C | 109.5 |
C8—C14—C13 | 108.5 (3) | H30B—C30—H30C | 109.5 |
| | | |
C10—C1—C2—C3 | 13.3 (6) | C8—C9—C11—C12 | −47.6 (4) |
C1—C2—C3—O31 | 78.4 (4) | C12—C11—O111—C112 | 100.1 (4) |
C1—C2—C3—C4 | −41.3 (5) | C9—C11—O111—C112 | −132.6 (3) |
C2—C3—O31—C32 | 123.7 (4) | C11—O111—C112—O113 | −6.4 (7) |
C4—C3—O31—C32 | −114.5 (4) | C11—O111—C112—C114 | 174.6 (3) |
C3—O31—C32—O33 | 5.1 (7) | O111—C11—C12—C13 | 157.0 (3) |
C3—O31—C32—C34 | −174.7 (4) | C9—C11—C12—C13 | 36.3 (5) |
O31—C3—C4—C29 | 62.1 (4) | C11—C12—C13—C18 | −103.3 (3) |
C2—C3—C4—C29 | −180.0 (3) | C11—C12—C13—C17 | 136.2 (3) |
O31—C3—C4—C28 | 179.6 (3) | C11—C12—C13—C14 | 20.8 (4) |
C2—C3—C4—C28 | −62.5 (4) | C7—C8—C14—C15 | −65.6 (4) |
O31—C3—C4—C5 | −61.4 (4) | C9—C8—C14—C15 | 164.2 (3) |
C2—C3—C4—C5 | 56.5 (4) | C7—C8—C14—C30 | 55.4 (4) |
C29—C4—C5—C10 | −165.6 (3) | C9—C8—C14—C30 | −74.8 (4) |
C28—C4—C5—C10 | 74.7 (4) | C7—C8—C14—C13 | −178.2 (2) |
C3—C4—C5—C10 | −42.8 (4) | C9—C8—C14—C13 | 51.6 (3) |
C29—C4—C5—C6 | −38.3 (4) | C12—C13—C14—C15 | 173.9 (3) |
C28—C4—C5—C6 | −158.0 (3) | C18—C13—C14—C15 | −63.4 (3) |
C3—C4—C5—C6 | 84.5 (4) | C17—C13—C14—C15 | 49.1 (3) |
C10—C5—C6—C7 | −24.0 (4) | C12—C13—C14—C30 | 64.1 (3) |
C4—C5—C6—C7 | −153.8 (3) | C18—C13—C14—C30 | −173.2 (2) |
C5—C6—C7—O71 | −161.7 (2) | C17—C13—C14—C30 | −60.7 (3) |
C5—C6—C7—C8 | −35.9 (4) | C12—C13—C14—C8 | −63.7 (3) |
C6—C7—O71—C72 | −77.9 (4) | C18—C13—C14—C8 | 59.0 (3) |
C8—C7—O71—C72 | 150.7 (3) | C17—C13—C14—C8 | 171.5 (2) |
C7—O71—C72—O73 | 0.7 (5) | C30—C14—C15—C16 | 78.2 (3) |
C7—O71—C72—C74 | 179.5 (3) | C8—C14—C15—C16 | −155.2 (3) |
O71—C7—C8—C14 | 50.9 (3) | C13—C14—C15—C16 | −38.2 (3) |
C6—C7—C8—C14 | −75.8 (4) | C14—C15—C16—C17 | 13.6 (4) |
O71—C7—C8—C9 | −175.8 (2) | C12—C13—C17—C21 | 74.3 (4) |
C6—C7—C8—C9 | 57.5 (4) | C18—C13—C17—C21 | −48.4 (4) |
C7—C8—C9—C19 | 106.0 (3) | C14—C13—C17—C21 | −165.7 (3) |
C14—C8—C9—C19 | −118.5 (3) | C12—C13—C17—C16 | −160.1 (3) |
C7—C8—C9—C10 | −16.5 (4) | C18—C13—C17—C16 | 77.2 (3) |
C14—C8—C9—C10 | 119.1 (3) | C14—C13—C17—C16 | −40.1 (3) |
C7—C8—C9—C11 | −133.5 (3) | C15—C16—C17—C21 | 146.2 (3) |
C14—C8—C9—C11 | 2.0 (4) | C15—C16—C17—C13 | 16.6 (4) |
C2—C1—C10—C5 | −0.2 (6) | C13—C17—C21—C20 | −58.1 (4) |
C2—C1—C10—C9 | −180.0 (3) | C16—C17—C21—C20 | −178.3 (3) |
C6—C5—C10—C1 | −115.1 (4) | C13—C17—C21—C22 | 179.4 (3) |
C4—C5—C10—C1 | 15.9 (5) | C16—C17—C21—C22 | 59.2 (4) |
C6—C5—C10—C9 | 64.7 (4) | C20—C21—C22—C23 | 68.7 (4) |
C4—C5—C10—C9 | −164.4 (3) | C17—C21—C22—C23 | −167.2 (3) |
C19—C9—C10—C1 | 16.1 (5) | C21—C22—C23—C24 | −177.7 (4) |
C11—C9—C10—C1 | −103.2 (4) | C22—C23—C24—C25A | −161.7 (8) |
C8—C9—C10—C1 | 138.2 (3) | C22—C23—C24—C25 | 168.6 (7) |
C19—C9—C10—C5 | −163.7 (3) | C25A—C24—C25—C27 | −31.3 (18) |
C11—C9—C10—C5 | 77.1 (3) | C23—C24—C25—C27 | 78.1 (12) |
C8—C9—C10—C5 | −41.6 (4) | C25A—C24—C25—C26 | 88 (2) |
C19—C9—C11—O111 | −48.5 (3) | C23—C24—C25—C26 | −162.4 (10) |
C10—C9—C11—O111 | 71.2 (3) | C23—C24—C25A—C26A | 162.4 (13) |
C8—C9—C11—O111 | −169.0 (2) | C25—C24—C25A—C26A | −115 (3) |
C19—C9—C11—C12 | 72.9 (4) | C23—C24—C25A—C27A | −78.1 (16) |
C10—C9—C11—C12 | −167.4 (3) | C25—C24—C25A—C27A | 5.0 (17) |
Experimental details
| (I) | (II) | (Irt) | (IIrt) |
Crystal data |
Chemical formula | C36H58O6 | C36H58O6 | C36H58O6 | C36H58O6 |
Mr | 586.82 | 586.82 | 586.82 | 586.82 |
Crystal system, space group | Orthorhombic, P212121 | Orthorhombic, P212121 | Orthorhombic, P212121 | Orthorhombic, P212121 |
Temperature (K) | 100 | 190 | 295 | 295 |
a, b, c (Å) | 14.0270 (8), 19.6354 (10), 26.2445 (12) | 9.0958 (9), 14.8510 (16), 25.526 (2) | 14.4800 (12), 19.8818 (13), 26.882 (2) | 9.0756 (7), 14.9566 (17), 26.008 (2) |
V (Å3) | 7228.4 (6) | 3448.1 (6) | 7739.0 (10) | 3530.3 (6) |
Z | 8 | 4 | 8 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.07 | 0.08 | 0.07 | 0.07 |
Crystal size (mm) | 0.5 × 0.2 × 0.2 | 0.35 × 0.3 × 0.1 | 0.5 × 0.2 × 0.2 | 0.35 × 0.3 × 0.1 |
|
Data collection |
Diffractometer | Kuma KM-4 CCD four-circle diffractometer | Kuma KM-4 CCD four-circle diffractometer | Kuma KM-4 CCD four-circle diffractometer | Kuma KM-4 CCD four-circle diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33755, 7355, 4921 | 16585, 4159, 2124 | 71201, 7878, 3204 | 21091, 4264, 2109 |
Rint | 0.045 | 0.081 | 0.097 | 0.047 |
(sin θ/λ)max (Å−1) | 0.606 | 0.639 | 0.606 | 0.639 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.147, 0.94 | 0.055, 0.078, 0.99 | 0.095, 0.276, 1.01 | 0.051, 0.126, 0.89 |
No. of reflections | 7355 | 4159 | 7878 | 4264 |
No. of parameters | 838 | 412 | 786 | 412 |
No. of restraints | 164 | 8 | 205 | 38 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.21 | 0.19, −0.18 | 0.59, −0.39 | 0.15, −0.14 |
Absolute structure | ? | ? | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2A—H2A2···O117i | 0.99 | 2.58 | 3.512 (6) | 156.3 |
C21A—H21A···O73Aii | 1.00 | 2.55 | 3.298 (5) | 131.9 |
C29A—H292···O73B | 0.96 | 2.49 | 3.437 (5) | 171.4 |
C2B—H2B2···O113iii | 0.99 | 2.66 | 3.482 (6) | 140.2 |
C34B—H34F···O117iv | 0.96 | 2.40 | 3.354 (5) | 175.1 |
C74B—H74F···O33Av | 0.96 | 2.62 | 3.577 (6) | 171.7 |
C21B—H21B···O73Bv | 1.00 | 2.54 | 3.308 (5) | 133.1 |
C29B—H295···O73A | 0.96 | 2.53 | 3.469 (5) | 167.2 |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z+2; (iii) x+1, y, z; (iv) −x+2, y−1/2, −z+3/2; (v) x+1/2, −y+5/2, −z+2. |
Hydrogen-bond geometry (Å, º) for (Irt) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2A—H2A1···O117i | 0.97 | 2.62 | 3.534 (14) | 157.7 |
C21A—H21A···O73Aii | 0.98 | 2.73 | 3.476 (10) | 132.9 |
C29A—H292···O73B | 0.99 | 2.57 | 3.553 (11) | 176.3 |
C2B—H2B2···O113iii | 0.97 | 2.58 | 3.429 (14) | 146.4 |
C34B—H34F···O117iv | 0.98 | 2.65 | 3.630 (13) | 171.0 |
C74B—H74F···O33Av | 0.98 | 2.82 | 3.792 (13) | 175.9 |
C21B—H21B···O73Bv | 0.98 | 2.68 | 3.410 (11) | 131.4 |
C29B—H295···O73A | 0.99 | 2.60 | 3.558 (12) | 163.1 |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z+2; (iii) x+1, y, z; (iv) −x+2, y−1/2, −z+3/2; (v) x+1/2, −y+5/2, −z+2. |
Table 2. The asymmetry parameters top | (IA) | (IB) | (II) |
A | ΔC2(2-3): 6.8 | ΔC2(2-3):5.4 | ΔC2(1-10): 0.76 |
B | ΔCs(5-8): 4.8 | ΔCs(5-8): 7.8 | ΔC2(6): 14.6 |
| ΔC2(5-10): 17.2 | ΔC2(5-10): 13.8 | ΔC2(5-10): 16.9 |
C1 | ΔCs(9): 10.2 | ΔCs(9): 7.8 | ΔC2(8-9): 18.7 |
| ΔC2(9-11): 1.4 | ΔC2(9-11): 4.1 | ΔCs(11): 15.8 |
| ΔCs(8): 20.7 | ΔCs(8): 20.9 | |
| ΔC2(11-12): 22.0 | ΔC2(11-12): 24.1 | |
D | ΔC2(13-14): 1.50 | ΔC2(13-14): 0.61 | ΔC2(13-14): 1.53 |
| | | |
1 For ring C in (I) the smallest and largest values of
asymmetry parameters are given. |
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Cucurbitacins, a large group of tetracyclic triterpenes, have the 19(10→9 b)abeo-lanostane (cucurbitane) carbon skeleton. These natural products have been isolated from various plants (Lavie & Glotter, 1971; Chen et al., 2005, and references cited therein; Miró, 1995). Cucurbitacins attract considerable attention owing to their unique structural features, multi-functionality and diverse biological activities (Chen et al., 2005; Miró, 1995).
The cucurbitacins are biogenetically derived from 2,3-oxidosqualene via 10α-cucurbita-5,24-diene-3β-ol (cucurbitadienol) as the crucial intermediate (Shibuya et al., 2004). In chemical synthesis, the cucurbitane derivatives are available from the reaction of 9-substituted lanostane derivatives via C-9 carbocationic intermediates (Paryzek, 1976, 1979; Edwards & Paryzek, 1983; Edwards & Kolt, 1987).
Several crystallographic analyses of cucurbitacins have aimed to establish unambiguously the structure of compounds isolated from natural sources. Besides other characteristic features, most natural cucurbitacins are characterized by the presence of the 5,6-double bond in the carbon skeleton. Accordingly, X-ray data for a number of cucurbit-5-ene derivatives have been accumulated, namely 10α-cucurbitadienol C-3 acetate (Nes et al., 1991), cucurbit-5-ene-3,22,23,24,25-pentaol (Okabe et al., 1980), (20R)-16-α-acetoxy-20-hydroxy-24,25,26,27-tetranor- 2β-(β-D-tetra-acetylglucopyranosyloxy)-10α-cucurbit-5-en-3,11, 22-trione trihydrate (Weinges et al., 1989), cucurbitacin E (Wu et al., 2004), 3β-hydroxy-7β,25-dimethoxycucurbita- 5,23(E)-diene (Harinantenaina et al., 2006), datiscoside bis-(p-iodobenzoate) dihydrate(Restivo et al., 1973), datiscoside dibenzene solvate (Sasamori et al., 1983) and 3β,16β-dihydroxy-7β-ethoxycucurbita-5,24-diene (Fujimoto et al., 1986).
In our investigation of the Lewis acid catalyzed reaction of 9β,11β-epoxy-5α-lanostane derivative, a series of compounds having the rearranged lanostane skeleton have been isolated and characterized. Spectroscopic methods (mostly 1H and 13C NMR) identified two compounds as the cucurbit-5(10)-ene and 5α-cucurbit-1(10)-ene derivatives, indicating the presence of the double bond in a rather unusual position in ring B (Figs. 1 and 2 show the nomenclature of the rings). There are only a few structurally characterized compounds with the 5(10)-ene steroid skeleton and even fewer with the 1(10)-ene analogue. A search of the Cambridge Structural Database (Allen, 2002; Version 5.30, November 2008), using a search fragment that excluded additional fused rings, gave 11 hits for the former and only two for the latter. We report here the crystal structures of the isomeric 5(10)-ene and 1(10)-ene cucurbitane derivatives 3β,7α,11β-triacetoxycucurbit-5(10)-ene, (I), and 3β,7α,11β-triacetoxy-5α-cucurbit-1(10)-ene, (II).
Crystals of both (I) and (II) proved very difficult to grow, resulting in samples of limited diffraction quality. We related this to the presence in both structures of disorder, which persisted despite the data collection temperature being lowered to 100 (1) K for (I) and to 190 (1) K for (II). The higher temperature employed for (II) was mandated by a decline in diffraction quality upon further cooling. The disorder affects the chain fragments; the alternative positions were resolved for five terminal atoms in molecule A of (I), (IA), with site-occupancy factors of 0.7/0.3, for four atoms in molecule B of (I) [(IB), 0.5/0.5] and for three atoms in (II) [0.631 (13)/0.369 (13)].
In (I), there are two symmetry-independent molecules in the asymmetric part of the unit cell. A normal probability plot (International Tables for X-ray Crystallography, 1974, Vol. IV, pp. 293–309; Abrahams & Keve, 1971) shows that the differences between the independent molecules in this case are statistical only and not systematic in nature. For the bond lengths in the ordered part of the molecule, the correlation factor R2 between the experimental and theoretical values is 0.96, the deviation of the a parameter (or slope in y = ax + b, in this case y = 1.64x - 0.05) from unity points to the typical underestimation of the s.u. values, while the small value of the b parameter indicates the lack of systematic errors. There is, in fact, quite good pseudo-twofold symmetry axis along the c-axis direction, which connects the main parts of those otherwise independent molecules. For the ordered part of the molecules the mean values of the combination of the coordinates (xA + xB, yA + yB, zA - zB) are 1.122 (7), 2.001 (3) and -0.001 (4), consistent with an approximate twofold axis along z at (0.561, 1.000, z).
The bond lengths and angles are close to typical values; the mean values of the Csp3—Csp3 bonds are 1.54 (2) Å in both structures. The relevant parameters that establish the location of the endocyclic C═C double bonds are C5A═C10A [1.352 (5) Å] and C5B═ C10B [1.334 (5) Å] in (I), and C1═C10 [1.333 (4) Å] in (II).
The different placement of the double bond heavily influences the conformations of the four-ring skeletons, and it is notable that the two symmetry-independent molecules in (I) have very similar conformations. In (I), rings A and B are close to the half-chair conformation (B less so than A), with an almost coplanar ring junction. In (II), ring A is again close to half-chair, of course with a different location for the approximate local twofold axis, but ring B is closer to a distorted twist-boat conformation, and the ring junction is cisoid. The most unexpected differences are observed in the conformations of ring C, apparently unaffected by the differences in ring A. The former is close to a standard chair conformation in (I), while in (II) this conformation can be described as a distorted boat. This latter conformation has not been observed previously in any of the steroids having a similar ring structure with a double bond in either the C1═C10 or C5═C10 positions. The B/C junction is cis in (I), but in (II) it is significantly flattened; the torsion angles around the junction bond C8—C9 are -18.4 (4) and 2.3 (4)°. Finally, rings D are quite regular half-chairs in both structures. The symmetry of the rings can be described by referring to the ideal symmetry, using so-called asymmetry parameters (Duax & Norton, 1975; see Table 2). The orientation of some of the acetoxy groups also differs in the two isomers. The 3β acetoxy group is in the equatorial position in (I), while it is in the axial position in (II), while the 11β substituent is closer to an axial position in (I), but almost in an equatorial position in (II). The 7α acetoxy group is in both compounds in the equatorial position, and the methyl groups C18, C19 and C30 are all axial.
The alkyl chain disorder illustrated in Fig. 3 is observed at both room and lower temperature, suggesting that it is static rather than dynamic in nature. The conformation along the chain (C20···C26 and C20···C27) can be described as g-ttg+ and g-ttt (g+ttg+ and g+ttt) in (IA), g-ttg- and g-ttg+ (g-ttt and g-ttg-) in (IB), and g+ttg+ and g+ttt (g+ttg- and g+ttg+) in (II). The symbols in parentheses refer to the second alternative position of the chain.
The crystal structure of (I) features a number of relatively weak but directional C—H···O contacts (Table 1) which are generally symmetrical with respect to both symmetry-independent molecules (cf. C2, C21 and C29), and they connect both kinds of molecules (i.e. there are A···B contacts as well as A···A and B···B ones). The structure of (II) lacks such contacts.