research communications
Unusual thermolysis of azacyclic allene under microwave conditions: RS,3aSR,8RS,8aRS)-methyl 5,6-dimethoxy-3a,10-dimethyl-1-phenyl-3,3a,8,8a-tetrahydro-3,8-(epiminomethano)cyclopenta[a]indene-2-carboxylate from synchrotron X-ray diffraction
of (3aDepartment of Pharmaceutical Chemistry, Faculty of Chemistry, VNU University of Science, 19 Le Thanh Tong, Hoan Kiem, Hanoi 100000, Vietnam, bOrganic Chemistry Department, Peoples' Friendship University of Russia, (RUDN University), Miklukho-Maklay St., 6, Moscow 117198, Russian Federation, cNational Research Centre "Kurchatov Institute", 1 Acad. Kurchatov Sq., Moscow 123182, Russian Federation, and dInorganic Chemistry Department, Peoples' Friendship University of Russia, (RUDN University), Miklukho-Maklay St., 6, Moscow 117198, Russian Federation
*Correspondence e-mail: huschemical.lab@gmail.com
The title compound, C25H27NO4 (I), the product of the unusual thermolysis of azacyclic allene methyl 10,11-dimethoxy-3,8-dimethyl-6-phenyl-3-azabenzo[d]cyclodeca-4,6,7-triene-5-carboxylate, represents a bicyclic heterosystem and crystallizes in the monoclinic P21/c with three crystallographically independent molecules in the These independent molecules adopt very similar geometries and differ only in the conformations of the two methoxy substituents on the benzene ring. In two of the three independent molecules, both methoxy groups are almost coplanar with the benzene ring [the C—C—O—Me torsion angles are 10.8 (2), 12.3 (2), 9.1 (2) and 13.6 (3)°], whereas in the third molecule, one of the methoxy groups is practically coplanar to and the other methoxy group is roughly perpendicular to the benzene ring, the C—C—O—Me torsion angles being 14.1 (2) and 76.5 (2)°. The molecule of (I) comprises a fused tetracyclic system containing two five-membered rings (cyclopentenes) and two six-membered rings (piperidine and benzene). The five-membered rings have the usual with the methyl-subsituted C atom as the flap in each molecule, and the six-membered piperidine ring has a chair conformation. The methyl substituent at the N atom occupies the sterically favourable equatorial position. The carboxylate group lies almost within the basal plane of the parent cyclopentene ring [making dihedral angle of 11.68 (8), 18.94 (9) and 15.16 (9)° in the three independent molecules], while the phenyl substituent is twisted by 48.26 (6), 42.04 (6) and 41.28 (6)° (for the three independent molecules) relative to this plane. In the crystal, molecules of (I) form stacks along the b-axis direction. The molecules are arranged at van der Waals distances.
Keywords: crystal structure; azacyclic allenes; thermolysis; microwave synthesis; (epiminomethano)cyclopenta[a]indene; 3-benzazepine; synchrotron X-ray diffraction.
CCDC reference: 1579823
1. Chemical context
The allene fragment is a part of some natural compounds – , 1976; Batzold et al., 1977). Bicyclic comprising ten-membered sesquiterpene have been isolated from the Vernonia plants of South America (Bohlmann et al., 1980; Jakupovic et al., 1985; Warning et al., 1987). Natural functionalized are inhibitors of enzymes that exhibit cytotoxic and antiviral activity (Krause & Hoffmann-Röder, 2004). However, heterocyclic allene systems are practically unexplored. Nitrogen-containing nonatrienes-3,6,7 were obtained for the first time in 1984 with a yield of 8–10% (Sashida & Tsuchiya, 1984). Further, the synthesis of 1-azadeca(undeca)-4,5-dien-2-ones has been carried out (Perscheid et al., 2011).
acids, The vast majority of them contain a non-cyclic allene fragment. Ten-membered with an allene fragment in bacteria have already been studied (Batzold & Robinson, 1975Recently, we proposed a relatively simple synthesis of benzoazadecatrienes-4,6,7 from 1R-1-phenylethynyl tetrahydroisoquinolines and activated terminal in trifluoroethanol at 256 K (Voskressensky et al., 2017). However, the thermal transformations of such strained systems have not yet been studied.
In this work, the thermolysis of an azacyclic allene under microwave conditions was carried out by our research group. The structure of the product of this unusual reaction was established unambiguously by synchrotron X-ray diffraction study.
2. Structural commentary
The title compound crystallizes with three crystallographically independent molecules (A, B and C, containing atoms N10, N32 and N54, respectively) in the (Fig. 1). These independent molecules adopt very similar geometries and differ only in the conformations of the two methoxy substituents at the benzene ring. In two of the three independent molecules, both methoxy groups are almost coplanar to the benzene ring [the C—C—O—Me torsion angles are 10.8 (2) and 12.3 (2)° in molecule A and 9.1 (2) and 13.6 (3)° in B], whereas in the third molecule, C, one of the methoxy groups is practically coplanar with and the other methoxy group is roughly perpendicular to the benzene ring, the C—C—O—Me torsion angles being 14.1 (2) and 76.5 (2)°].
The molecule of (I) comprises a fused tetracyclic system containing two five-membered rings (cyclopentenes) and two six-membered rings (piperidine and benzene) (Fig. 1). The five-membered rings have the usual with the methyl-subsituted C atom as the flap in each molecule, and the six-membered piperidine ring has a chair conformation. The methyl substituent at the nitrogen atom occupies the sterically favourable equatorial position. The carboxylate group lies almost within the basal plane of the parent cyclopentene ring, making dihedral angles of 11.68 (8), 18.94 (9) and 15.16 (9)°, respectively, in molecules A, B and C, while the phenyl substituent is twisted by 48.26 (6), 42.04 (6) and 41.28 (6)° relative to this plane in molecules A, B and C, respectively.
The title molecule possesses four asymmetric centers at the C3, C3A, C8 and C8A carbon atoms and can have potentially numerous The crystal of (I) is racemic and consists of enantiomeric pairs with the following of the centers: rac-3R*,3aS*,8R*,8aR*.
3. Supramolecular features
The crystal packing motif of molecules of (I) is stacking along the crystallographic b axis (Fig. 2). The molecules are arranged at van der Waals distances.
4. Synthesis and crystallization
A stirred solution of cyclic allene (0.13 g, 0.32 mmol) in toluene (5 mL) was heated at 453 K for 1 h in a microwave reactor (Anton Paar Monowave 300) (Fig. 3). The solvent was evaporated in vacuo, and the residue recrystallized from ether to give 60 mg of colourless crystals of (I) in a yield of 50%, m.p. = 422–424 K (ether).
1H NMR (CDCl3, 600 MHz): δ = 1.47 (3H, s, 3a-Me), 2.21 (3H, s, NMe), 2.47 (1H, dd, J = 2.5 Hz, J = 10.7 Hz, 9-CH), 2.65 (1H, dd, J = 2.5 Hz, J = 10.7 Hz, 9-CH), 3.09–3.10 (1H, m, 8-CH), 3.22 (1H, d, J = 5.0 Hz, 8a-CH), 3.67 (1H, d, J = 1.7 Hz, 3-CH), 3.69 (3H, s, OMe), 3.88 (3H, s, OMe), 3.91 (3H, s, OMe), 6.73 (1H, s, H7), 6.74 (1H, s, H4), 7.35–7.40 (3H, m, Ph), 7.47–7.48 (2H, m, Ph); 13C NMR (DMSO-d6, 150 MHz): δ = 18.3, 42.3, 42.6, 51.1, 51.2, 55.7, 55.8, 59.6, 67.9, 72.8, 106.9, 107.1, 124.9, 127.9 (2 C), 128.0 (2 C), 128.5, 135.1, 137.1, 137.3, 147.8, 148.3, 151.1, 166.3; m/z: 406 [M+H]+. Analysis calculated for C25H27NO4 (%): C 74.03, H 6.71, N 3.45; found (%): C 74.04, H 6.71, N 3.41.
5. Refinement
Crystal data, data collection and structure . The X-ray diffraction study was carried out on the `Belok' beamline of the National Research Center `Kurchatov Institute' (Moscow, Russian Federation) using a Rayonix SX165 CCD detector. A total of 720 images were collected using an oscillation range of 1.0° (φ scan mode, two different crystal orientations) and corrected for absorption using the Scala program (Evans, 2006). The data were indexed, integrated and scaled using the utility iMOSFLM in CCP4 (Battye et al., 2011).
details are summarized in Table 1Hydrogen atoms were placed in calculated positions with C—H = 0.95–1.00 Å and refined in the riding model with fixed isotropic displacement parameters [Uiso(H) = 1.5Ueq(C) for the CH3-groups and 1.2Ueq(C) for the other groups].
A rather large number of reflections have been omitted for the following reasons: (i) In order to achieve better Iσ statistics for high-angle reflections, we selected exposure times so as to admit a minor fraction of intensity overloads in the low-angle part of the detector. These low-angle reflections with imprecisely measured intensities were excluded from the final steps of the (ii) In the present setup of the synchrotron diffractometer, the low-temperature device eclipses a small region of the 2D detector near the high-angle limit. This small shadowed region was not masked during integration of the diffraction frames, which erroneously resulted in zero intensity for some reflections.
Supporting information
CCDC reference: 1579823
https://doi.org/10.1107/S2056989017014864/yk2110sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017014864/yk2110Isup2.hkl
Data collection: Marccd (Doyle, 2011); cell
iMOSFLM (Battye et al., 2011); data reduction: iMOSFLM (Battye et al., 2011); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C25H27NO4 | F(000) = 2592 |
Mr = 405.47 | Dx = 1.261 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.96990 Å |
a = 26.404 (5) Å | Cell parameters from 600 reflections |
b = 7.9303 (16) Å | θ = 3.6–36.0° |
c = 30.720 (6) Å | µ = 0.18 mm−1 |
β = 95.09 (3)° | T = 100 K |
V = 6407 (2) Å3 | Prism, colourless |
Z = 12 | 0.25 × 0.24 × 0.21 mm |
Rayonix SX165 CCD diffractometer | 10086 reflections with I > 2σ(I) |
/f scan | Rint = 0.071 |
Absorption correction: multi-scan (Scala; Evans, 2006) | θmax = 39.7°, θmin = 3.5° |
Tmin = 0.940, Tmax = 0.951 | h = −33→33 |
74044 measured reflections | k = −8→10 |
13622 independent reflections | l = −39→39 |
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)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.0696P)2 + 0.8571P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
13622 reflections | Δρmax = 0.46 e Å−3 |
827 parameters | Δρmin = −0.38 e Å−3 |
0 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: difference Fourier map | Extinction coefficient: 0.00120 (18) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.27574 (4) | 0.67806 (16) | 0.64919 (4) | 0.0291 (3) | |
O2 | 0.19523 (4) | 0.75446 (16) | 0.65782 (4) | 0.0293 (3) | |
O3 | 0.30254 (4) | 0.29541 (15) | 0.38931 (4) | 0.0266 (3) | |
O4 | 0.26028 (4) | 0.55159 (15) | 0.35018 (3) | 0.0244 (3) | |
C1 | 0.16537 (6) | 0.6161 (2) | 0.57029 (5) | 0.0201 (3) | |
C2 | 0.21299 (6) | 0.6304 (2) | 0.59036 (5) | 0.0198 (3) | |
C3 | 0.25165 (6) | 0.5938 (2) | 0.55724 (5) | 0.0195 (3) | |
H3 | 0.2835 | 0.5432 | 0.5717 | 0.023* | |
C3A | 0.22152 (6) | 0.4638 (2) | 0.52660 (5) | 0.0195 (3) | |
C3B | 0.23500 (6) | 0.4674 (2) | 0.47966 (5) | 0.0197 (3) | |
C4 | 0.26706 (6) | 0.3619 (2) | 0.45845 (5) | 0.0210 (4) | |
H4 | 0.2842 | 0.2711 | 0.4736 | 0.025* | |
C5 | 0.27349 (6) | 0.3925 (2) | 0.41453 (5) | 0.0210 (4) | |
C6 | 0.24940 (6) | 0.5322 (2) | 0.39281 (5) | 0.0206 (4) | |
C7 | 0.21706 (6) | 0.6363 (2) | 0.41435 (5) | 0.0218 (4) | |
H7 | 0.2006 | 0.7297 | 0.3998 | 0.026* | |
C7A | 0.20952 (6) | 0.6002 (2) | 0.45771 (5) | 0.0196 (3) | |
C8 | 0.17978 (6) | 0.6978 (2) | 0.48975 (5) | 0.0205 (4) | |
H8 | 0.1478 | 0.7487 | 0.4756 | 0.025* | |
C8A | 0.16948 (6) | 0.5569 (2) | 0.52346 (5) | 0.0201 (3) | |
H8A | 0.1407 | 0.4817 | 0.5127 | 0.024* | |
C9 | 0.21579 (6) | 0.8298 (2) | 0.51258 (5) | 0.0207 (3) | |
H9A | 0.2247 | 0.9154 | 0.4911 | 0.025* | |
H9B | 0.1985 | 0.8878 | 0.5357 | 0.025* | |
N10 | 0.26251 (5) | 0.74768 (17) | 0.53217 (4) | 0.0200 (3) | |
C11 | 0.11459 (6) | 0.6438 (2) | 0.58631 (5) | 0.0205 (3) | |
C12 | 0.10117 (7) | 0.5756 (2) | 0.62547 (6) | 0.0291 (4) | |
H12 | 0.1255 | 0.5114 | 0.6431 | 0.035* | |
C13 | 0.05300 (7) | 0.5997 (2) | 0.63919 (6) | 0.0330 (4) | |
H13 | 0.0445 | 0.5506 | 0.6658 | 0.040* | |
C14 | 0.01719 (6) | 0.6951 (2) | 0.61416 (6) | 0.0294 (4) | |
H14 | −0.0156 | 0.7138 | 0.6237 | 0.035* | |
C15 | 0.03000 (6) | 0.7628 (2) | 0.57498 (6) | 0.0286 (4) | |
H15 | 0.0058 | 0.8286 | 0.5577 | 0.034* | |
C16 | 0.07783 (6) | 0.7357 (2) | 0.56054 (5) | 0.0248 (4) | |
H16 | 0.0856 | 0.7797 | 0.5331 | 0.030* | |
C17 | 0.23166 (6) | 0.6887 (2) | 0.63484 (5) | 0.0216 (4) | |
C18 | 0.21198 (7) | 0.8065 (3) | 0.70192 (5) | 0.0349 (5) | |
H18A | 0.2401 | 0.8868 | 0.7012 | 0.052* | |
H18B | 0.2235 | 0.7076 | 0.7192 | 0.052* | |
H18C | 0.1837 | 0.8602 | 0.7152 | 0.052* | |
C19 | 0.22182 (6) | 0.2883 (2) | 0.54690 (5) | 0.0243 (4) | |
H19A | 0.1990 | 0.2142 | 0.5287 | 0.036* | |
H19B | 0.2103 | 0.2954 | 0.5763 | 0.036* | |
H19C | 0.2564 | 0.2424 | 0.5487 | 0.036* | |
C20 | 0.24521 (7) | 0.7058 (2) | 0.32898 (5) | 0.0300 (4) | |
H20A | 0.2585 | 0.7100 | 0.3002 | 0.045* | |
H20B | 0.2588 | 0.8010 | 0.3467 | 0.045* | |
H20C | 0.2080 | 0.7124 | 0.3254 | 0.045* | |
C21 | 0.32021 (7) | 0.1375 (2) | 0.40771 (6) | 0.0308 (4) | |
H21A | 0.3390 | 0.0767 | 0.3865 | 0.046* | |
H21B | 0.2911 | 0.0697 | 0.4149 | 0.046* | |
H21C | 0.3427 | 0.1583 | 0.4343 | 0.046* | |
C22 | 0.29463 (6) | 0.8685 (2) | 0.55748 (5) | 0.0239 (4) | |
H22A | 0.2753 | 0.9199 | 0.5798 | 0.036* | |
H22B | 0.3057 | 0.9564 | 0.5380 | 0.036* | |
H22C | 0.3245 | 0.8103 | 0.5716 | 0.036* | |
O5 | 0.04526 (4) | 0.27952 (16) | 0.18932 (4) | 0.0306 (3) | |
O6 | 0.12346 (4) | 0.37557 (16) | 0.17935 (4) | 0.0302 (3) | |
O7 | 0.04963 (4) | −0.16000 (15) | 0.44959 (4) | 0.0258 (3) | |
O8 | 0.11516 (4) | 0.06677 (16) | 0.48935 (3) | 0.0255 (3) | |
C23 | 0.16239 (6) | 0.1905 (2) | 0.25797 (5) | 0.0188 (3) | |
C24 | 0.11291 (6) | 0.2176 (2) | 0.24310 (5) | 0.0185 (3) | |
C25 | 0.07877 (6) | 0.1781 (2) | 0.27969 (5) | 0.0185 (3) | |
H25 | 0.0444 | 0.1382 | 0.2677 | 0.022* | |
C25A | 0.10949 (6) | 0.0350 (2) | 0.30487 (5) | 0.0193 (3) | |
C25B | 0.10346 (6) | 0.0281 (2) | 0.35363 (5) | 0.0192 (3) | |
C26 | 0.07316 (6) | −0.0761 (2) | 0.37696 (5) | 0.0204 (3) | |
H26 | 0.0508 | −0.1554 | 0.3623 | 0.024* | |
C27 | 0.07641 (6) | −0.0616 (2) | 0.42257 (5) | 0.0214 (4) | |
C28 | 0.10869 (6) | 0.0601 (2) | 0.44392 (5) | 0.0217 (4) | |
C29 | 0.13786 (6) | 0.1658 (2) | 0.42003 (5) | 0.0219 (4) | |
H29 | 0.1591 | 0.2493 | 0.4343 | 0.026* | |
C29A | 0.13541 (6) | 0.1474 (2) | 0.37498 (5) | 0.0205 (3) | |
C30 | 0.16122 (6) | 0.2481 (2) | 0.34132 (5) | 0.0204 (4) | |
H30 | 0.1958 | 0.2889 | 0.3526 | 0.025* | |
C30A | 0.16310 (6) | 0.1158 (2) | 0.30369 (5) | 0.0198 (3) | |
H30A | 0.1911 | 0.0318 | 0.3098 | 0.024* | |
C31 | 0.12553 (6) | 0.3929 (2) | 0.32492 (5) | 0.0210 (4) | |
H31A | 0.1217 | 0.4732 | 0.3491 | 0.025* | |
H31B | 0.1406 | 0.4545 | 0.3012 | 0.025* | |
N32 | 0.07522 (5) | 0.32672 (17) | 0.30861 (4) | 0.0199 (3) | |
C33 | 0.21087 (6) | 0.2266 (2) | 0.23888 (5) | 0.0201 (3) | |
C34 | 0.21906 (6) | 0.1952 (2) | 0.19520 (5) | 0.0259 (4) | |
H34 | 0.1926 | 0.1476 | 0.1761 | 0.031* | |
C35 | 0.26551 (7) | 0.2328 (2) | 0.17949 (6) | 0.0310 (4) | |
H35 | 0.2705 | 0.2098 | 0.1498 | 0.037* | |
C36 | 0.30473 (7) | 0.3035 (2) | 0.20663 (6) | 0.0293 (4) | |
H36 | 0.3362 | 0.3308 | 0.1956 | 0.035* | |
C37 | 0.29726 (6) | 0.3338 (2) | 0.25022 (6) | 0.0279 (4) | |
H37 | 0.3237 | 0.3829 | 0.2691 | 0.033* | |
C38 | 0.25138 (6) | 0.2928 (2) | 0.26632 (5) | 0.0235 (4) | |
H38 | 0.2473 | 0.3097 | 0.2964 | 0.028* | |
C39 | 0.09013 (6) | 0.2923 (2) | 0.20193 (5) | 0.0209 (4) | |
C40 | 0.10380 (8) | 0.4429 (3) | 0.13759 (6) | 0.0380 (5) | |
H40A | 0.0890 | 0.3515 | 0.1191 | 0.057* | |
H40B | 0.1315 | 0.4960 | 0.1233 | 0.057* | |
H40C | 0.0776 | 0.5272 | 0.1420 | 0.057* | |
C41 | 0.10082 (6) | −0.1333 (2) | 0.28122 (5) | 0.0230 (4) | |
H41A | 0.1229 | −0.2193 | 0.2958 | 0.035* | |
H41B | 0.1088 | −0.1213 | 0.2508 | 0.035* | |
H41C | 0.0652 | −0.1672 | 0.2819 | 0.035* | |
C42 | 0.07612 (7) | 0.1543 (2) | 0.50948 (5) | 0.0289 (4) | |
H42A | 0.0696 | 0.2630 | 0.4949 | 0.043* | |
H42B | 0.0870 | 0.1734 | 0.5404 | 0.043* | |
H42C | 0.0449 | 0.0867 | 0.5070 | 0.043* | |
C43 | 0.02597 (7) | −0.3088 (2) | 0.43054 (6) | 0.0338 (4) | |
H43A | −0.0009 | −0.2763 | 0.4080 | 0.051* | |
H43B | 0.0112 | −0.3745 | 0.4533 | 0.051* | |
H43C | 0.0515 | −0.3771 | 0.4173 | 0.051* | |
C44 | 0.04325 (6) | 0.4598 (2) | 0.28805 (5) | 0.0245 (4) | |
H44A | 0.0379 | 0.5475 | 0.3096 | 0.037* | |
H44B | 0.0104 | 0.4122 | 0.2769 | 0.037* | |
H44C | 0.0600 | 0.5089 | 0.2638 | 0.037* | |
O9 | 0.38416 (4) | 0.20757 (16) | 0.51668 (4) | 0.0281 (3) | |
O10 | 0.46237 (4) | 0.31084 (16) | 0.50926 (4) | 0.0283 (3) | |
O11 | 0.36852 (5) | −0.25476 (16) | 0.76825 (4) | 0.0337 (3) | |
O12 | 0.40905 (5) | −0.00499 (16) | 0.81049 (4) | 0.0346 (3) | |
C45 | 0.49830 (6) | 0.1339 (2) | 0.59067 (5) | 0.0194 (3) | |
C46 | 0.44971 (6) | 0.1511 (2) | 0.57266 (5) | 0.0191 (3) | |
C47 | 0.41323 (6) | 0.0987 (2) | 0.60641 (5) | 0.0204 (4) | |
H47 | 0.3809 | 0.0510 | 0.5920 | 0.025* | |
C47A | 0.44527 (6) | −0.0399 (2) | 0.63274 (5) | 0.0208 (4) | |
C47B | 0.43428 (6) | −0.0539 (2) | 0.68019 (5) | 0.0217 (4) | |
C48 | 0.40304 (6) | −0.1680 (2) | 0.70002 (5) | 0.0246 (4) | |
H48 | 0.3862 | −0.2562 | 0.6836 | 0.030* | |
C49 | 0.39714 (6) | −0.1497 (2) | 0.74438 (5) | 0.0261 (4) | |
C50 | 0.42073 (7) | −0.0153 (2) | 0.76786 (5) | 0.0274 (4) | |
C51 | 0.45268 (6) | 0.0966 (2) | 0.74807 (5) | 0.0263 (4) | |
H51 | 0.4691 | 0.1863 | 0.7642 | 0.032* | |
C51A | 0.45971 (6) | 0.0730 (2) | 0.70407 (5) | 0.0233 (4) | |
C52 | 0.48757 (6) | 0.1839 (2) | 0.67344 (5) | 0.0221 (4) | |
H52 | 0.5199 | 0.2318 | 0.6878 | 0.027* | |
C52A | 0.49672 (6) | 0.0566 (2) | 0.63598 (5) | 0.0206 (4) | |
H52A | 0.5263 | −0.0194 | 0.6439 | 0.025* | |
C53 | 0.45036 (6) | 0.3205 (2) | 0.65498 (5) | 0.0223 (4) | |
H53A | 0.4424 | 0.3980 | 0.6787 | 0.027* | |
H53B | 0.4662 | 0.3871 | 0.6326 | 0.027* | |
N54 | 0.40313 (5) | 0.24188 (18) | 0.63536 (4) | 0.0219 (3) | |
C55 | 0.54798 (6) | 0.1758 (2) | 0.57438 (5) | 0.0201 (3) | |
C56 | 0.55974 (6) | 0.1444 (2) | 0.53162 (5) | 0.0235 (4) | |
H56 | 0.5348 | 0.0956 | 0.5112 | 0.028* | |
C57 | 0.60753 (6) | 0.1839 (2) | 0.51869 (6) | 0.0273 (4) | |
H57 | 0.6151 | 0.1607 | 0.4896 | 0.033* | |
C58 | 0.64441 (6) | 0.2571 (2) | 0.54792 (5) | 0.0258 (4) | |
H58 | 0.6768 | 0.2855 | 0.5388 | 0.031* | |
C59 | 0.63324 (6) | 0.2882 (2) | 0.59062 (5) | 0.0253 (4) | |
H59 | 0.6581 | 0.3390 | 0.6108 | 0.030* | |
C60 | 0.58591 (6) | 0.2452 (2) | 0.60395 (5) | 0.0229 (4) | |
H60 | 0.5792 | 0.2630 | 0.6335 | 0.027* | |
C61 | 0.42839 (6) | 0.2241 (2) | 0.53060 (5) | 0.0212 (4) | |
C62 | 0.44417 (7) | 0.3744 (3) | 0.46658 (5) | 0.0337 (4) | |
H62A | 0.4133 | 0.4410 | 0.4689 | 0.050* | |
H62B | 0.4366 | 0.2796 | 0.4466 | 0.050* | |
H62C | 0.4704 | 0.4457 | 0.4553 | 0.050* | |
C63 | 0.44378 (7) | −0.2058 (2) | 0.60785 (5) | 0.0260 (4) | |
H63A | 0.4673 | −0.2860 | 0.6231 | 0.039* | |
H63B | 0.4538 | −0.1864 | 0.5783 | 0.039* | |
H63C | 0.4092 | −0.2519 | 0.6061 | 0.039* | |
C64 | 0.42125 (8) | 0.1456 (3) | 0.83337 (6) | 0.0406 (5) | |
H64A | 0.4076 | 0.1415 | 0.8620 | 0.061* | |
H64B | 0.4064 | 0.2415 | 0.8167 | 0.061* | |
H64C | 0.4583 | 0.1586 | 0.8374 | 0.061* | |
C65 | 0.34943 (7) | −0.4060 (2) | 0.74740 (6) | 0.0362 (5) | |
H65A | 0.3315 | −0.4725 | 0.7681 | 0.054* | |
H65B | 0.3778 | −0.4719 | 0.7378 | 0.054* | |
H65C | 0.3259 | −0.3770 | 0.7220 | 0.054* | |
C66 | 0.36905 (6) | 0.3679 (2) | 0.61390 (5) | 0.0253 (4) | |
H66A | 0.3386 | 0.3120 | 0.6001 | 0.038* | |
H66B | 0.3865 | 0.4270 | 0.5915 | 0.038* | |
H66C | 0.3592 | 0.4492 | 0.6356 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0238 (6) | 0.0403 (8) | 0.0228 (6) | 0.0006 (6) | −0.0001 (5) | −0.0031 (5) |
O2 | 0.0268 (6) | 0.0402 (8) | 0.0210 (6) | 0.0067 (6) | 0.0022 (5) | −0.0091 (5) |
O3 | 0.0314 (7) | 0.0264 (7) | 0.0226 (6) | 0.0071 (5) | 0.0060 (5) | −0.0020 (5) |
O4 | 0.0300 (6) | 0.0262 (7) | 0.0170 (5) | −0.0005 (5) | 0.0025 (5) | 0.0001 (5) |
C1 | 0.0208 (8) | 0.0184 (9) | 0.0213 (8) | 0.0004 (7) | 0.0033 (6) | 0.0016 (7) |
C2 | 0.0204 (8) | 0.0195 (9) | 0.0196 (8) | −0.0001 (7) | 0.0027 (6) | 0.0007 (7) |
C3 | 0.0189 (8) | 0.0208 (9) | 0.0186 (7) | 0.0017 (7) | 0.0013 (6) | 0.0009 (7) |
C3A | 0.0195 (8) | 0.0193 (9) | 0.0198 (8) | 0.0003 (7) | 0.0024 (6) | −0.0008 (7) |
C3B | 0.0185 (8) | 0.0196 (9) | 0.0209 (8) | −0.0015 (7) | 0.0012 (6) | −0.0021 (7) |
C4 | 0.0198 (8) | 0.0205 (9) | 0.0224 (8) | −0.0007 (7) | 0.0002 (6) | 0.0004 (7) |
C5 | 0.0191 (8) | 0.0224 (9) | 0.0216 (8) | −0.0004 (7) | 0.0022 (6) | −0.0044 (7) |
C6 | 0.0208 (8) | 0.0242 (9) | 0.0165 (7) | −0.0040 (7) | −0.0002 (6) | −0.0011 (7) |
C7 | 0.0213 (8) | 0.0218 (9) | 0.0217 (8) | −0.0008 (7) | −0.0011 (6) | 0.0003 (7) |
C7A | 0.0177 (8) | 0.0193 (9) | 0.0215 (8) | −0.0021 (7) | −0.0005 (6) | −0.0023 (7) |
C8 | 0.0203 (8) | 0.0228 (9) | 0.0181 (8) | 0.0033 (7) | 0.0007 (6) | 0.0005 (7) |
C8A | 0.0174 (8) | 0.0209 (9) | 0.0218 (8) | −0.0006 (7) | 0.0014 (6) | −0.0018 (7) |
C9 | 0.0211 (8) | 0.0197 (9) | 0.0214 (8) | 0.0022 (7) | 0.0028 (6) | 0.0015 (7) |
N10 | 0.0186 (7) | 0.0199 (7) | 0.0214 (7) | 0.0002 (6) | 0.0011 (5) | −0.0003 (6) |
C11 | 0.0196 (8) | 0.0214 (9) | 0.0207 (8) | −0.0027 (7) | 0.0025 (6) | −0.0013 (7) |
C12 | 0.0264 (9) | 0.0306 (10) | 0.0308 (9) | 0.0036 (8) | 0.0061 (7) | 0.0076 (8) |
C13 | 0.0310 (10) | 0.0354 (11) | 0.0345 (10) | −0.0002 (8) | 0.0146 (8) | 0.0077 (9) |
C14 | 0.0212 (9) | 0.0313 (11) | 0.0367 (10) | −0.0027 (8) | 0.0085 (7) | −0.0046 (8) |
C15 | 0.0205 (9) | 0.0378 (11) | 0.0271 (9) | 0.0037 (8) | −0.0002 (7) | −0.0032 (8) |
C16 | 0.0222 (8) | 0.0329 (10) | 0.0191 (8) | 0.0027 (8) | 0.0010 (6) | −0.0010 (7) |
C17 | 0.0230 (9) | 0.0224 (9) | 0.0199 (8) | 0.0005 (7) | 0.0048 (6) | 0.0016 (7) |
C18 | 0.0402 (11) | 0.0440 (12) | 0.0203 (9) | 0.0054 (9) | 0.0020 (7) | −0.0089 (8) |
C19 | 0.0274 (9) | 0.0227 (10) | 0.0227 (8) | −0.0006 (7) | 0.0021 (7) | −0.0007 (7) |
C20 | 0.0361 (10) | 0.0325 (11) | 0.0211 (8) | 0.0020 (8) | 0.0006 (7) | 0.0061 (8) |
C21 | 0.0351 (10) | 0.0272 (10) | 0.0308 (9) | 0.0084 (8) | 0.0067 (8) | −0.0024 (8) |
C22 | 0.0208 (8) | 0.0247 (10) | 0.0260 (8) | −0.0038 (7) | 0.0022 (7) | −0.0037 (7) |
O5 | 0.0254 (6) | 0.0397 (8) | 0.0259 (6) | −0.0022 (6) | −0.0025 (5) | 0.0053 (6) |
O6 | 0.0285 (7) | 0.0382 (8) | 0.0235 (6) | −0.0069 (6) | 0.0000 (5) | 0.0125 (6) |
O7 | 0.0278 (6) | 0.0281 (7) | 0.0222 (6) | −0.0059 (5) | 0.0058 (5) | 0.0051 (5) |
O8 | 0.0254 (6) | 0.0354 (7) | 0.0157 (5) | 0.0021 (5) | 0.0023 (4) | 0.0013 (5) |
C23 | 0.0211 (8) | 0.0175 (9) | 0.0181 (7) | −0.0006 (7) | 0.0031 (6) | −0.0023 (6) |
C24 | 0.0211 (8) | 0.0176 (9) | 0.0171 (7) | −0.0017 (7) | 0.0027 (6) | −0.0006 (6) |
C25 | 0.0192 (8) | 0.0201 (9) | 0.0164 (7) | −0.0016 (7) | 0.0027 (6) | −0.0004 (6) |
C25A | 0.0204 (8) | 0.0205 (9) | 0.0170 (7) | −0.0011 (7) | 0.0011 (6) | 0.0007 (7) |
C25B | 0.0173 (8) | 0.0200 (9) | 0.0203 (8) | 0.0006 (7) | 0.0008 (6) | 0.0011 (7) |
C26 | 0.0194 (8) | 0.0201 (9) | 0.0213 (8) | −0.0006 (7) | 0.0000 (6) | 0.0020 (7) |
C27 | 0.0206 (8) | 0.0229 (9) | 0.0211 (8) | 0.0005 (7) | 0.0032 (6) | 0.0046 (7) |
C28 | 0.0226 (8) | 0.0269 (10) | 0.0153 (7) | 0.0024 (7) | 0.0000 (6) | 0.0026 (7) |
C29 | 0.0205 (8) | 0.0243 (9) | 0.0206 (8) | −0.0027 (7) | 0.0001 (6) | 0.0004 (7) |
C29A | 0.0194 (8) | 0.0227 (9) | 0.0191 (8) | −0.0009 (7) | 0.0008 (6) | 0.0021 (7) |
C30 | 0.0193 (8) | 0.0247 (9) | 0.0172 (7) | −0.0050 (7) | 0.0014 (6) | −0.0005 (7) |
C30A | 0.0184 (8) | 0.0221 (9) | 0.0189 (8) | 0.0006 (7) | 0.0017 (6) | 0.0005 (7) |
C31 | 0.0242 (8) | 0.0200 (9) | 0.0191 (8) | −0.0040 (7) | 0.0045 (6) | −0.0021 (7) |
N32 | 0.0214 (7) | 0.0184 (7) | 0.0200 (7) | −0.0005 (6) | 0.0026 (5) | −0.0018 (6) |
C33 | 0.0201 (8) | 0.0184 (9) | 0.0223 (8) | 0.0013 (7) | 0.0041 (6) | 0.0008 (7) |
C34 | 0.0258 (9) | 0.0305 (10) | 0.0218 (8) | −0.0028 (8) | 0.0046 (7) | −0.0058 (7) |
C35 | 0.0302 (10) | 0.0395 (12) | 0.0248 (9) | −0.0016 (9) | 0.0109 (7) | −0.0027 (8) |
C36 | 0.0232 (9) | 0.0323 (11) | 0.0336 (10) | 0.0014 (8) | 0.0102 (7) | 0.0021 (8) |
C37 | 0.0206 (9) | 0.0320 (11) | 0.0314 (9) | −0.0012 (8) | 0.0038 (7) | −0.0004 (8) |
C38 | 0.0220 (8) | 0.0291 (10) | 0.0196 (8) | 0.0000 (7) | 0.0029 (6) | −0.0003 (7) |
C39 | 0.0223 (9) | 0.0212 (9) | 0.0196 (8) | −0.0020 (7) | 0.0034 (6) | −0.0019 (7) |
C40 | 0.0441 (12) | 0.0455 (13) | 0.0230 (9) | −0.0081 (10) | −0.0040 (8) | 0.0134 (9) |
C41 | 0.0272 (9) | 0.0196 (9) | 0.0218 (8) | −0.0012 (7) | −0.0005 (7) | −0.0006 (7) |
C42 | 0.0282 (9) | 0.0388 (11) | 0.0202 (8) | 0.0005 (8) | 0.0043 (7) | −0.0016 (8) |
C43 | 0.0391 (11) | 0.0301 (11) | 0.0335 (10) | −0.0092 (9) | 0.0108 (8) | 0.0021 (8) |
C44 | 0.0253 (9) | 0.0226 (9) | 0.0264 (8) | 0.0021 (7) | 0.0068 (7) | 0.0019 (7) |
O9 | 0.0229 (6) | 0.0366 (8) | 0.0243 (6) | −0.0016 (5) | −0.0010 (5) | 0.0026 (5) |
O10 | 0.0267 (6) | 0.0341 (7) | 0.0238 (6) | −0.0040 (5) | 0.0006 (5) | 0.0099 (5) |
O11 | 0.0405 (7) | 0.0343 (8) | 0.0281 (6) | −0.0021 (6) | 0.0128 (5) | 0.0076 (6) |
O12 | 0.0493 (8) | 0.0340 (8) | 0.0212 (6) | −0.0002 (6) | 0.0071 (5) | 0.0008 (6) |
C45 | 0.0222 (8) | 0.0170 (9) | 0.0194 (8) | −0.0006 (7) | 0.0046 (6) | −0.0021 (7) |
C46 | 0.0197 (8) | 0.0188 (9) | 0.0189 (8) | −0.0016 (7) | 0.0029 (6) | −0.0015 (7) |
C47 | 0.0184 (8) | 0.0237 (9) | 0.0193 (8) | −0.0013 (7) | 0.0018 (6) | 0.0008 (7) |
C47A | 0.0198 (8) | 0.0215 (9) | 0.0211 (8) | −0.0003 (7) | 0.0021 (6) | 0.0016 (7) |
C47B | 0.0193 (8) | 0.0239 (9) | 0.0222 (8) | 0.0020 (7) | 0.0030 (6) | 0.0035 (7) |
C48 | 0.0236 (9) | 0.0256 (10) | 0.0248 (8) | 0.0019 (7) | 0.0027 (7) | 0.0046 (7) |
C49 | 0.0271 (9) | 0.0263 (10) | 0.0256 (9) | 0.0031 (8) | 0.0063 (7) | 0.0072 (8) |
C50 | 0.0324 (10) | 0.0320 (11) | 0.0184 (8) | 0.0078 (8) | 0.0056 (7) | 0.0069 (7) |
C51 | 0.0293 (9) | 0.0275 (10) | 0.0218 (8) | 0.0036 (8) | 0.0008 (7) | 0.0009 (7) |
C51A | 0.0227 (8) | 0.0268 (10) | 0.0203 (8) | 0.0040 (7) | 0.0011 (6) | 0.0039 (7) |
C52 | 0.0227 (8) | 0.0256 (10) | 0.0181 (8) | −0.0027 (7) | 0.0012 (6) | −0.0017 (7) |
C52A | 0.0179 (8) | 0.0216 (9) | 0.0225 (8) | 0.0013 (7) | 0.0021 (6) | 0.0016 (7) |
C53 | 0.0246 (9) | 0.0217 (9) | 0.0207 (8) | −0.0016 (7) | 0.0034 (6) | −0.0013 (7) |
N54 | 0.0204 (7) | 0.0236 (8) | 0.0219 (7) | 0.0017 (6) | 0.0033 (5) | −0.0003 (6) |
C55 | 0.0194 (8) | 0.0185 (9) | 0.0227 (8) | 0.0018 (7) | 0.0031 (6) | 0.0004 (7) |
C56 | 0.0220 (8) | 0.0260 (10) | 0.0232 (8) | −0.0024 (7) | 0.0046 (6) | −0.0043 (7) |
C57 | 0.0274 (9) | 0.0304 (10) | 0.0252 (9) | 0.0001 (8) | 0.0087 (7) | −0.0013 (8) |
C58 | 0.0208 (8) | 0.0274 (10) | 0.0303 (9) | −0.0008 (7) | 0.0074 (7) | 0.0010 (8) |
C59 | 0.0198 (8) | 0.0287 (10) | 0.0273 (9) | −0.0023 (7) | 0.0009 (7) | 0.0020 (8) |
C60 | 0.0226 (8) | 0.0253 (9) | 0.0211 (8) | 0.0010 (7) | 0.0031 (6) | 0.0004 (7) |
C61 | 0.0232 (9) | 0.0209 (9) | 0.0199 (8) | −0.0001 (7) | 0.0045 (6) | −0.0018 (7) |
C62 | 0.0393 (11) | 0.0379 (12) | 0.0235 (9) | −0.0027 (9) | 0.0012 (8) | 0.0098 (8) |
C63 | 0.0274 (9) | 0.0228 (10) | 0.0277 (9) | −0.0012 (7) | 0.0018 (7) | 0.0016 (7) |
C64 | 0.0562 (13) | 0.0413 (13) | 0.0230 (9) | −0.0053 (10) | −0.0031 (9) | −0.0061 (9) |
C65 | 0.0394 (11) | 0.0330 (11) | 0.0373 (11) | −0.0078 (9) | 0.0088 (8) | 0.0058 (9) |
C66 | 0.0251 (9) | 0.0247 (10) | 0.0267 (9) | 0.0044 (7) | 0.0057 (7) | 0.0026 (7) |
O1—C17 | 1.2105 (19) | C31—N32 | 1.474 (2) |
O2—C17 | 1.3477 (19) | C31—H31A | 0.9900 |
O2—C18 | 1.447 (2) | C31—H31B | 0.9900 |
O3—C5 | 1.3737 (19) | N32—C44 | 1.459 (2) |
O3—C21 | 1.435 (2) | C33—C34 | 1.400 (2) |
O4—C6 | 1.3741 (18) | C33—C38 | 1.403 (2) |
O4—C20 | 1.425 (2) | C34—C35 | 1.390 (2) |
C1—C2 | 1.355 (2) | C34—H34 | 0.9500 |
C1—C11 | 1.485 (2) | C35—C36 | 1.389 (3) |
C1—C8A | 1.527 (2) | C35—H35 | 0.9500 |
C2—C17 | 1.485 (2) | C36—C37 | 1.392 (2) |
C2—C3 | 1.532 (2) | C36—H36 | 0.9500 |
C3—N10 | 1.485 (2) | C37—C38 | 1.387 (2) |
C3—C3A | 1.565 (2) | C37—H37 | 0.9500 |
C3—H3 | 1.0000 | C38—H38 | 0.9500 |
C3A—C3B | 1.516 (2) | C40—H40A | 0.9800 |
C3A—C19 | 1.525 (2) | C40—H40B | 0.9800 |
C3A—C8A | 1.555 (2) | C40—H40C | 0.9800 |
C3B—C7A | 1.391 (2) | C41—H41A | 0.9800 |
C3B—C4 | 1.393 (2) | C41—H41B | 0.9800 |
C4—C5 | 1.396 (2) | C41—H41C | 0.9800 |
C4—H4 | 0.9500 | C42—H42A | 0.9800 |
C5—C6 | 1.415 (2) | C42—H42B | 0.9800 |
C6—C7 | 1.396 (2) | C42—H42C | 0.9800 |
C7—C7A | 1.394 (2) | C43—H43A | 0.9800 |
C7—H7 | 0.9500 | C43—H43B | 0.9800 |
C7A—C8 | 1.524 (2) | C43—H43C | 0.9800 |
C8—C9 | 1.541 (2) | C44—H44A | 0.9800 |
C8—C8A | 1.563 (2) | C44—H44B | 0.9800 |
C8—H8 | 1.0000 | C44—H44C | 0.9800 |
C8A—H8A | 1.0000 | O9—C61 | 1.2148 (19) |
C9—N10 | 1.475 (2) | O10—C61 | 1.346 (2) |
C9—H9A | 0.9900 | O10—C62 | 1.446 (2) |
C9—H9B | 0.9900 | O11—C49 | 1.379 (2) |
N10—C22 | 1.458 (2) | O11—C65 | 1.430 (2) |
C11—C12 | 1.393 (2) | O12—C50 | 1.3744 (19) |
C11—C16 | 1.401 (2) | O12—C64 | 1.409 (2) |
C12—C13 | 1.388 (2) | C45—C46 | 1.358 (2) |
C12—H12 | 0.9500 | C45—C55 | 1.483 (2) |
C13—C14 | 1.389 (3) | C45—C52A | 1.525 (2) |
C13—H13 | 0.9500 | C46—C61 | 1.481 (2) |
C14—C15 | 1.387 (2) | C46—C47 | 1.534 (2) |
C14—H14 | 0.9500 | C47—N54 | 1.481 (2) |
C15—C16 | 1.392 (2) | C47—C47A | 1.567 (2) |
C15—H15 | 0.9500 | C47—H47 | 1.0000 |
C16—H16 | 0.9500 | C47A—C47B | 1.515 (2) |
C18—H18A | 0.9800 | C47A—C63 | 1.520 (2) |
C18—H18B | 0.9800 | C47A—C52A | 1.555 (2) |
C18—H18C | 0.9800 | C47B—C51A | 1.383 (2) |
C19—H19A | 0.9800 | C47B—C48 | 1.400 (2) |
C19—H19B | 0.9800 | C48—C49 | 1.393 (2) |
C19—H19C | 0.9800 | C48—H48 | 0.9500 |
C20—H20A | 0.9800 | C49—C50 | 1.402 (3) |
C20—H20B | 0.9800 | C50—C51 | 1.400 (3) |
C20—H20C | 0.9800 | C51—C51A | 1.393 (2) |
C21—H21A | 0.9800 | C51—H51 | 0.9500 |
C21—H21B | 0.9800 | C51A—C52 | 1.524 (2) |
C21—H21C | 0.9800 | C52—C53 | 1.537 (2) |
C22—H22A | 0.9800 | C52—C52A | 1.566 (2) |
C22—H22B | 0.9800 | C52—H52 | 1.0000 |
C22—H22C | 0.9800 | C52A—H52A | 1.0000 |
O5—C39 | 1.2177 (19) | C53—N54 | 1.474 (2) |
O6—C39 | 1.3414 (19) | C53—H53A | 0.9900 |
O6—C40 | 1.443 (2) | C53—H53B | 0.9900 |
O7—C27 | 1.3789 (19) | N54—C66 | 1.462 (2) |
O7—C43 | 1.435 (2) | C55—C56 | 1.399 (2) |
O8—C28 | 1.3919 (18) | C55—C60 | 1.403 (2) |
O8—C42 | 1.428 (2) | C56—C57 | 1.392 (2) |
C23—C24 | 1.362 (2) | C56—H56 | 0.9500 |
C23—C33 | 1.483 (2) | C57—C58 | 1.391 (2) |
C23—C30A | 1.523 (2) | C57—H57 | 0.9500 |
C24—C39 | 1.476 (2) | C58—C59 | 1.392 (2) |
C24—C25 | 1.534 (2) | C58—H58 | 0.9500 |
C25—N32 | 1.484 (2) | C59—C60 | 1.392 (2) |
C25—C25A | 1.560 (2) | C59—H59 | 0.9500 |
C25—H25 | 1.0000 | C60—H60 | 0.9500 |
C25A—C25B | 1.521 (2) | C62—H62A | 0.9800 |
C25A—C41 | 1.527 (2) | C62—H62B | 0.9800 |
C25A—C30A | 1.557 (2) | C62—H62C | 0.9800 |
C25B—C26 | 1.392 (2) | C63—H63A | 0.9800 |
C25B—C29A | 1.393 (2) | C63—H63B | 0.9800 |
C26—C27 | 1.401 (2) | C63—H63C | 0.9800 |
C26—H26 | 0.9500 | C64—H64A | 0.9800 |
C27—C28 | 1.410 (2) | C64—H64B | 0.9800 |
C28—C29 | 1.391 (2) | C64—H64C | 0.9800 |
C29—C29A | 1.387 (2) | C65—H65A | 0.9800 |
C29—H29 | 0.9500 | C65—H65B | 0.9800 |
C29A—C30 | 1.515 (2) | C65—H65C | 0.9800 |
C30—C31 | 1.541 (2) | C66—H66A | 0.9800 |
C30—C30A | 1.566 (2) | C66—H66B | 0.9800 |
C30—H30 | 1.0000 | C66—H66C | 0.9800 |
C30A—H30A | 1.0000 | ||
C17—O2—C18 | 115.32 (13) | H31A—C31—H31B | 108.1 |
C5—O3—C21 | 116.44 (13) | C44—N32—C31 | 111.03 (13) |
C6—O4—C20 | 117.24 (13) | C44—N32—C25 | 112.34 (12) |
C2—C1—C11 | 131.73 (15) | C31—N32—C25 | 112.55 (12) |
C2—C1—C8A | 108.29 (13) | C34—C33—C38 | 117.90 (15) |
C11—C1—C8A | 119.97 (13) | C34—C33—C23 | 123.82 (15) |
C1—C2—C17 | 131.57 (15) | C38—C33—C23 | 118.26 (14) |
C1—C2—C3 | 109.17 (13) | C35—C34—C33 | 120.70 (16) |
C17—C2—C3 | 118.94 (13) | C35—C34—H34 | 119.6 |
N10—C3—C2 | 111.07 (13) | C33—C34—H34 | 119.6 |
N10—C3—C3A | 109.91 (12) | C36—C35—C34 | 120.82 (16) |
C2—C3—C3A | 101.02 (12) | C36—C35—H35 | 119.6 |
N10—C3—H3 | 111.5 | C34—C35—H35 | 119.6 |
C2—C3—H3 | 111.5 | C35—C36—C37 | 119.05 (16) |
C3A—C3—H3 | 111.5 | C35—C36—H36 | 120.5 |
C3B—C3A—C19 | 114.39 (13) | C37—C36—H36 | 120.5 |
C3B—C3A—C8A | 102.28 (12) | C38—C37—C36 | 120.35 (16) |
C19—C3A—C8A | 115.55 (13) | C38—C37—H37 | 119.8 |
C3B—C3A—C3 | 114.21 (13) | C36—C37—H37 | 119.8 |
C19—C3A—C3 | 111.78 (13) | C37—C38—C33 | 121.11 (15) |
C8A—C3A—C3 | 97.13 (12) | C37—C38—H38 | 119.4 |
C7A—C3B—C4 | 121.05 (14) | C33—C38—H38 | 119.4 |
C7A—C3B—C3A | 109.34 (14) | O5—C39—O6 | 122.77 (15) |
C4—C3B—C3A | 129.61 (15) | O5—C39—C24 | 123.36 (15) |
C3B—C4—C5 | 118.62 (15) | O6—C39—C24 | 113.86 (13) |
C3B—C4—H4 | 120.7 | O6—C40—H40A | 109.5 |
C5—C4—H4 | 120.7 | O6—C40—H40B | 109.5 |
O3—C5—C4 | 124.74 (15) | H40A—C40—H40B | 109.5 |
O3—C5—C6 | 115.02 (14) | O6—C40—H40C | 109.5 |
C4—C5—C6 | 120.24 (15) | H40A—C40—H40C | 109.5 |
O4—C6—C7 | 125.03 (15) | H40B—C40—H40C | 109.5 |
O4—C6—C5 | 114.44 (14) | C25A—C41—H41A | 109.5 |
C7—C6—C5 | 120.52 (14) | C25A—C41—H41B | 109.5 |
C7A—C7—C6 | 118.45 (15) | H41A—C41—H41B | 109.5 |
C7A—C7—H7 | 120.8 | C25A—C41—H41C | 109.5 |
C6—C7—H7 | 120.8 | H41A—C41—H41C | 109.5 |
C3B—C7A—C7 | 121.01 (15) | H41B—C41—H41C | 109.5 |
C3B—C7A—C8 | 109.04 (13) | O8—C42—H42A | 109.5 |
C7—C7A—C8 | 129.64 (15) | O8—C42—H42B | 109.5 |
C7A—C8—C9 | 107.86 (13) | H42A—C42—H42B | 109.5 |
C7A—C8—C8A | 101.22 (13) | O8—C42—H42C | 109.5 |
C9—C8—C8A | 108.69 (12) | H42A—C42—H42C | 109.5 |
C7A—C8—H8 | 112.8 | H42B—C42—H42C | 109.5 |
C9—C8—H8 | 112.8 | O7—C43—H43A | 109.5 |
C8A—C8—H8 | 112.8 | O7—C43—H43B | 109.5 |
C1—C8A—C3A | 102.94 (12) | H43A—C43—H43B | 109.5 |
C1—C8A—C8 | 115.81 (14) | O7—C43—H43C | 109.5 |
C3A—C8A—C8 | 100.12 (12) | H43A—C43—H43C | 109.5 |
C1—C8A—H8A | 112.3 | H43B—C43—H43C | 109.5 |
C3A—C8A—H8A | 112.3 | N32—C44—H44A | 109.5 |
C8—C8A—H8A | 112.3 | N32—C44—H44B | 109.5 |
N10—C9—C8 | 110.22 (13) | H44A—C44—H44B | 109.5 |
N10—C9—H9A | 109.6 | N32—C44—H44C | 109.5 |
C8—C9—H9A | 109.6 | H44A—C44—H44C | 109.5 |
N10—C9—H9B | 109.6 | H44B—C44—H44C | 109.5 |
C8—C9—H9B | 109.6 | C61—O10—C62 | 115.94 (13) |
H9A—C9—H9B | 108.1 | C49—O11—C65 | 117.15 (14) |
C22—N10—C9 | 110.70 (13) | C50—O12—C64 | 117.71 (15) |
C22—N10—C3 | 113.17 (12) | C46—C45—C55 | 132.22 (15) |
C9—N10—C3 | 112.43 (12) | C46—C45—C52A | 108.11 (13) |
C12—C11—C16 | 118.24 (15) | C55—C45—C52A | 119.67 (14) |
C12—C11—C1 | 122.36 (15) | C45—C46—C61 | 131.83 (14) |
C16—C11—C1 | 119.36 (14) | C45—C46—C47 | 108.93 (13) |
C13—C12—C11 | 121.27 (17) | C61—C46—C47 | 118.88 (13) |
C13—C12—H12 | 119.4 | N54—C47—C46 | 110.80 (13) |
C11—C12—H12 | 119.4 | N54—C47—C47A | 110.20 (12) |
C12—C13—C14 | 120.25 (16) | C46—C47—C47A | 101.34 (12) |
C12—C13—H13 | 119.9 | N54—C47—H47 | 111.4 |
C14—C13—H13 | 119.9 | C46—C47—H47 | 111.4 |
C15—C14—C13 | 119.00 (16) | C47A—C47—H47 | 111.4 |
C15—C14—H14 | 120.5 | C47B—C47A—C63 | 114.94 (14) |
C13—C14—H14 | 120.5 | C47B—C47A—C52A | 102.44 (13) |
C14—C15—C16 | 120.99 (17) | C63—C47A—C52A | 116.19 (14) |
C14—C15—H15 | 119.5 | C47B—C47A—C47 | 114.04 (13) |
C16—C15—H15 | 119.5 | C63—C47A—C47 | 111.00 (13) |
C15—C16—C11 | 120.19 (15) | C52A—C47A—C47 | 96.70 (13) |
C15—C16—H16 | 119.9 | C51A—C47B—C48 | 121.09 (15) |
C11—C16—H16 | 119.9 | C51A—C47B—C47A | 109.35 (14) |
O1—C17—O2 | 122.95 (15) | C48—C47B—C47A | 129.54 (15) |
O1—C17—C2 | 122.93 (14) | C49—C48—C47B | 118.67 (16) |
O2—C17—C2 | 114.11 (14) | C49—C48—H48 | 120.7 |
O2—C18—H18A | 109.5 | C47B—C48—H48 | 120.7 |
O2—C18—H18B | 109.5 | O11—C49—C48 | 124.86 (16) |
H18A—C18—H18B | 109.5 | O11—C49—C50 | 115.17 (14) |
O2—C18—H18C | 109.5 | C48—C49—C50 | 119.96 (16) |
H18A—C18—H18C | 109.5 | O12—C50—C51 | 124.83 (17) |
H18B—C18—H18C | 109.5 | O12—C50—C49 | 114.11 (15) |
C3A—C19—H19A | 109.5 | C51—C50—C49 | 121.06 (15) |
C3A—C19—H19B | 109.5 | C51A—C51—C50 | 118.25 (17) |
H19A—C19—H19B | 109.5 | C51A—C51—H51 | 120.9 |
C3A—C19—H19C | 109.5 | C50—C51—H51 | 120.9 |
H19A—C19—H19C | 109.5 | C47B—C51A—C51 | 120.81 (16) |
H19B—C19—H19C | 109.5 | C47B—C51A—C52 | 109.30 (14) |
O4—C20—H20A | 109.5 | C51—C51A—C52 | 129.37 (16) |
O4—C20—H20B | 109.5 | C51A—C52—C53 | 107.87 (13) |
H20A—C20—H20B | 109.5 | C51A—C52—C52A | 101.29 (13) |
O4—C20—H20C | 109.5 | C53—C52—C52A | 108.58 (13) |
H20A—C20—H20C | 109.5 | C51A—C52—H52 | 112.8 |
H20B—C20—H20C | 109.5 | C53—C52—H52 | 112.8 |
O3—C21—H21A | 109.5 | C52A—C52—H52 | 112.8 |
O3—C21—H21B | 109.5 | C45—C52A—C47A | 103.53 (12) |
H21A—C21—H21B | 109.5 | C45—C52A—C52 | 115.48 (14) |
O3—C21—H21C | 109.5 | C47A—C52A—C52 | 99.98 (12) |
H21A—C21—H21C | 109.5 | C45—C52A—H52A | 112.3 |
H21B—C21—H21C | 109.5 | C47A—C52A—H52A | 112.3 |
N10—C22—H22A | 109.5 | C52—C52A—H52A | 112.3 |
N10—C22—H22B | 109.5 | N54—C53—C52 | 110.03 (14) |
H22A—C22—H22B | 109.5 | N54—C53—H53A | 109.7 |
N10—C22—H22C | 109.5 | C52—C53—H53A | 109.7 |
H22A—C22—H22C | 109.5 | N54—C53—H53B | 109.7 |
H22B—C22—H22C | 109.5 | C52—C53—H53B | 109.7 |
C39—O6—C40 | 116.17 (13) | H53A—C53—H53B | 108.2 |
C27—O7—C43 | 116.59 (13) | C66—N54—C53 | 111.07 (13) |
C28—O8—C42 | 115.06 (12) | C66—N54—C47 | 112.94 (13) |
C24—C23—C33 | 132.29 (14) | C53—N54—C47 | 112.27 (12) |
C24—C23—C30A | 107.67 (13) | C56—C55—C60 | 118.20 (15) |
C33—C23—C30A | 119.97 (13) | C56—C55—C45 | 123.61 (15) |
C23—C24—C39 | 131.03 (15) | C60—C55—C45 | 118.14 (14) |
C23—C24—C25 | 109.29 (13) | C57—C56—C55 | 120.68 (16) |
C39—C24—C25 | 119.26 (13) | C57—C56—H56 | 119.7 |
N32—C25—C24 | 110.41 (13) | C55—C56—H56 | 119.7 |
N32—C25—C25A | 109.79 (12) | C58—C57—C56 | 120.66 (15) |
C24—C25—C25A | 101.45 (12) | C58—C57—H57 | 119.7 |
N32—C25—H25 | 111.6 | C56—C57—H57 | 119.7 |
C24—C25—H25 | 111.6 | C57—C58—C59 | 119.18 (15) |
C25A—C25—H25 | 111.6 | C57—C58—H58 | 120.4 |
C25B—C25A—C41 | 114.38 (13) | C59—C58—H58 | 120.4 |
C25B—C25A—C30A | 102.27 (12) | C60—C59—C58 | 120.32 (16) |
C41—C25A—C30A | 116.53 (13) | C60—C59—H59 | 119.8 |
C25B—C25A—C25 | 114.79 (13) | C58—C59—H59 | 119.8 |
C41—C25A—C25 | 110.51 (12) | C59—C60—C55 | 120.90 (15) |
C30A—C25A—C25 | 97.07 (12) | C59—C60—H60 | 119.5 |
C26—C25B—C29A | 120.83 (14) | C55—C60—H60 | 119.5 |
C26—C25B—C25A | 130.04 (14) | O9—C61—O10 | 123.04 (15) |
C29A—C25B—C25A | 109.12 (13) | O9—C61—C46 | 122.97 (15) |
C25B—C26—C27 | 118.64 (15) | O10—C61—C46 | 113.99 (14) |
C25B—C26—H26 | 120.7 | O10—C62—H62A | 109.5 |
C27—C26—H26 | 120.7 | O10—C62—H62B | 109.5 |
O7—C27—C26 | 124.50 (15) | H62A—C62—H62B | 109.5 |
O7—C27—C28 | 115.37 (14) | O10—C62—H62C | 109.5 |
C26—C27—C28 | 120.13 (14) | H62A—C62—H62C | 109.5 |
C29—C28—O8 | 118.79 (14) | H62B—C62—H62C | 109.5 |
C29—C28—C27 | 120.49 (14) | C47A—C63—H63A | 109.5 |
O8—C28—C27 | 120.50 (14) | C47A—C63—H63B | 109.5 |
C29A—C29—C28 | 118.94 (15) | H63A—C63—H63B | 109.5 |
C29A—C29—H29 | 120.5 | C47A—C63—H63C | 109.5 |
C28—C29—H29 | 120.5 | H63A—C63—H63C | 109.5 |
C29—C29A—C25B | 120.93 (15) | H63B—C63—H63C | 109.5 |
C29—C29A—C30 | 129.89 (15) | O12—C64—H64A | 109.5 |
C25B—C29A—C30 | 109.08 (13) | O12—C64—H64B | 109.5 |
C29A—C30—C31 | 108.47 (13) | H64A—C64—H64B | 109.5 |
C29A—C30—C30A | 101.31 (13) | O12—C64—H64C | 109.5 |
C31—C30—C30A | 108.45 (12) | H64A—C64—H64C | 109.5 |
C29A—C30—H30 | 112.6 | H64B—C64—H64C | 109.5 |
C31—C30—H30 | 112.6 | O11—C65—H65A | 109.5 |
C30A—C30—H30 | 112.6 | O11—C65—H65B | 109.5 |
C23—C30A—C25A | 104.16 (12) | H65A—C65—H65B | 109.5 |
C23—C30A—C30 | 114.93 (13) | O11—C65—H65C | 109.5 |
C25A—C30A—C30 | 99.80 (12) | H65A—C65—H65C | 109.5 |
C23—C30A—H30A | 112.3 | H65B—C65—H65C | 109.5 |
C25A—C30A—H30A | 112.3 | N54—C66—H66A | 109.5 |
C30—C30A—H30A | 112.3 | N54—C66—H66B | 109.5 |
N32—C31—C30 | 110.63 (13) | H66A—C66—H66B | 109.5 |
N32—C31—H31A | 109.5 | N54—C66—H66C | 109.5 |
C30—C31—H31A | 109.5 | H66A—C66—H66C | 109.5 |
N32—C31—H31B | 109.5 | H66B—C66—H66C | 109.5 |
C30—C31—H31B | 109.5 | ||
C11—C1—C2—C17 | −4.3 (3) | C29—C29A—C30—C30A | 154.58 (17) |
C8A—C1—C2—C17 | 177.21 (17) | C25B—C29A—C30—C30A | −29.07 (16) |
C11—C1—C2—C3 | −177.48 (16) | C24—C23—C30A—C25A | 23.32 (17) |
C8A—C1—C2—C3 | 3.99 (18) | C33—C23—C30A—C25A | −159.21 (14) |
C1—C2—C3—N10 | 85.35 (16) | C24—C23—C30A—C30 | −84.78 (16) |
C17—C2—C3—N10 | −88.86 (17) | C33—C23—C30A—C30 | 92.68 (17) |
C1—C2—C3—C3A | −31.19 (17) | C25B—C25A—C30A—C23 | −157.64 (12) |
C17—C2—C3—C3A | 154.60 (14) | C41—C25A—C30A—C23 | 76.86 (16) |
N10—C3—C3A—C3B | 32.76 (18) | C25—C25A—C30A—C23 | −40.30 (14) |
C2—C3—C3A—C3B | 150.15 (13) | C25B—C25A—C30A—C30 | −38.65 (15) |
N10—C3—C3A—C19 | 164.63 (13) | C41—C25A—C30A—C30 | −164.14 (13) |
C2—C3—C3A—C19 | −77.98 (15) | C25—C25A—C30A—C30 | 78.70 (13) |
N10—C3—C3A—C8A | −74.17 (14) | C29A—C30—C30A—C23 | 151.59 (13) |
C2—C3—C3A—C8A | 43.22 (14) | C31—C30—C30A—C23 | 37.56 (17) |
C19—C3A—C3B—C7A | 149.06 (14) | C29A—C30—C30A—C25A | 40.86 (14) |
C8A—C3A—C3B—C7A | 23.36 (17) | C31—C30—C30A—C25A | −73.17 (14) |
C3—C3A—C3B—C7A | −80.35 (16) | C29A—C30—C31—N32 | −54.65 (16) |
C19—C3A—C3B—C4 | −30.9 (2) | C30A—C30—C31—N32 | 54.58 (16) |
C8A—C3A—C3B—C4 | −156.63 (16) | C30—C31—N32—C44 | −172.92 (12) |
C3—C3A—C3B—C4 | 99.7 (2) | C30—C31—N32—C25 | −46.02 (16) |
C7A—C3B—C4—C5 | 0.4 (2) | C24—C25—N32—C44 | 73.76 (16) |
C3A—C3B—C4—C5 | −179.63 (15) | C25A—C25—N32—C44 | −175.20 (12) |
C21—O3—C5—C4 | 10.8 (2) | C24—C25—N32—C31 | −52.44 (16) |
C21—O3—C5—C6 | −169.50 (14) | C25A—C25—N32—C31 | 58.60 (16) |
C3B—C4—C5—O3 | −177.74 (15) | C24—C23—C33—C34 | −43.9 (3) |
C3B—C4—C5—C6 | 2.6 (2) | C30A—C23—C33—C34 | 139.35 (17) |
C20—O4—C6—C7 | 12.3 (2) | C24—C23—C33—C38 | 137.56 (19) |
C20—O4—C6—C5 | −168.59 (14) | C30A—C23—C33—C38 | −39.2 (2) |
O3—C5—C6—O4 | −2.0 (2) | C38—C33—C34—C35 | −1.7 (3) |
C4—C5—C6—O4 | 177.74 (14) | C23—C33—C34—C35 | 179.80 (17) |
O3—C5—C6—C7 | 177.21 (14) | C33—C34—C35—C36 | −0.5 (3) |
C4—C5—C6—C7 | −3.1 (2) | C34—C35—C36—C37 | 1.1 (3) |
O4—C6—C7—C7A | 179.67 (14) | C35—C36—C37—C38 | 0.4 (3) |
C5—C6—C7—C7A | 0.6 (2) | C36—C37—C38—C33 | −2.7 (3) |
C4—C3B—C7A—C7 | −2.9 (2) | C34—C33—C38—C37 | 3.2 (3) |
C3A—C3B—C7A—C7 | 177.10 (14) | C23—C33—C38—C37 | −178.16 (16) |
C4—C3B—C7A—C8 | −177.06 (14) | C40—O6—C39—O5 | −3.2 (2) |
C3A—C3B—C7A—C8 | 2.94 (18) | C40—O6—C39—C24 | 176.56 (15) |
C6—C7—C7A—C3B | 2.4 (2) | C23—C24—C39—O5 | 165.36 (17) |
C6—C7—C7A—C8 | 175.21 (15) | C25—C24—C39—O5 | −22.9 (2) |
C3B—C7A—C8—C9 | 86.25 (16) | C23—C24—C39—O6 | −14.4 (3) |
C7—C7A—C8—C9 | −87.25 (19) | C25—C24—C39—O6 | 157.40 (14) |
C3B—C7A—C8—C8A | −27.78 (16) | C55—C45—C46—C61 | −2.5 (3) |
C7—C7A—C8—C8A | 158.72 (16) | C52A—C45—C46—C61 | 177.20 (16) |
C2—C1—C8A—C3A | 25.11 (17) | C55—C45—C46—C47 | −175.48 (16) |
C11—C1—C8A—C3A | −153.63 (14) | C52A—C45—C46—C47 | 4.22 (18) |
C2—C1—C8A—C8 | −83.04 (17) | C45—C46—C47—N54 | 85.56 (16) |
C11—C1—C8A—C8 | 98.23 (17) | C61—C46—C47—N54 | −88.48 (17) |
C3B—C3A—C8A—C1 | −158.40 (13) | C45—C46—C47—C47A | −31.37 (17) |
C19—C3A—C8A—C1 | 76.66 (16) | C61—C46—C47—C47A | 154.60 (14) |
C3—C3A—C8A—C1 | −41.65 (14) | N54—C47—C47A—C47B | 32.61 (18) |
C3B—C3A—C8A—C8 | −38.74 (14) | C46—C47—C47A—C47B | 149.97 (13) |
C19—C3A—C8A—C8 | −163.67 (13) | N54—C47—C47A—C63 | 164.35 (13) |
C3—C3A—C8A—C8 | 78.01 (13) | C46—C47—C47A—C63 | −78.29 (15) |
C7A—C8—C8A—C1 | 149.93 (13) | N54—C47—C47A—C52A | −74.25 (14) |
C9—C8—C8A—C1 | 36.53 (18) | C46—C47—C47A—C52A | 43.12 (14) |
C7A—C8—C8A—C3A | 40.12 (14) | C63—C47A—C47B—C51A | 150.67 (14) |
C9—C8—C8A—C3A | −73.29 (15) | C52A—C47A—C47B—C51A | 23.74 (17) |
C7A—C8—C9—N10 | −53.83 (16) | C47—C47A—C47B—C51A | −79.52 (17) |
C8A—C8—C9—N10 | 55.13 (16) | C63—C47A—C47B—C48 | −31.1 (2) |
C8—C9—N10—C22 | −174.44 (12) | C52A—C47A—C47B—C48 | −158.03 (17) |
C8—C9—N10—C3 | −46.77 (16) | C47—C47A—C47B—C48 | 98.7 (2) |
C2—C3—N10—C22 | 74.47 (16) | C51A—C47B—C48—C49 | 1.2 (2) |
C3A—C3—N10—C22 | −174.60 (12) | C47A—C47B—C48—C49 | −176.84 (16) |
C2—C3—N10—C9 | −51.88 (17) | C65—O11—C49—C48 | 9.1 (2) |
C3A—C3—N10—C9 | 59.06 (16) | C65—O11—C49—C50 | −171.75 (15) |
C2—C1—C11—C12 | −48.2 (3) | C47B—C48—C49—O11 | −178.54 (15) |
C8A—C1—C11—C12 | 130.16 (17) | C47B—C48—C49—C50 | 2.4 (2) |
C2—C1—C11—C16 | 134.47 (19) | C64—O12—C50—C51 | 13.6 (3) |
C8A—C1—C11—C16 | −47.1 (2) | C64—O12—C50—C49 | −165.73 (16) |
C16—C11—C12—C13 | −1.0 (3) | O11—C49—C50—O12 | −3.4 (2) |
C1—C11—C12—C13 | −178.31 (17) | C48—C49—C50—O12 | 175.73 (15) |
C11—C12—C13—C14 | −0.9 (3) | O11—C49—C50—C51 | 177.20 (15) |
C12—C13—C14—C15 | 1.3 (3) | C48—C49—C50—C51 | −3.6 (3) |
C13—C14—C15—C16 | 0.2 (3) | O12—C50—C51—C51A | −178.05 (15) |
C14—C15—C16—C11 | −2.2 (3) | C49—C50—C51—C51A | 1.2 (3) |
C12—C11—C16—C15 | 2.5 (3) | C48—C47B—C51A—C51 | −3.6 (3) |
C1—C11—C16—C15 | 179.93 (16) | C47A—C47B—C51A—C51 | 174.76 (15) |
C18—O2—C17—O1 | −2.2 (2) | C48—C47B—C51A—C52 | −176.13 (15) |
C18—O2—C17—C2 | 177.75 (15) | C47A—C47B—C51A—C52 | 2.28 (18) |
C1—C2—C17—O1 | 172.56 (18) | C50—C51—C51A—C47B | 2.4 (2) |
C3—C2—C17—O1 | −14.8 (2) | C50—C51—C51A—C52 | 173.18 (16) |
C1—C2—C17—O2 | −7.4 (3) | C47B—C51A—C52—C53 | 86.89 (16) |
C3—C2—C17—O2 | 165.25 (14) | C51—C51A—C52—C53 | −84.8 (2) |
C33—C23—C24—C39 | 0.6 (3) | C47B—C51A—C52—C52A | −27.06 (17) |
C30A—C23—C24—C39 | 177.66 (16) | C51—C51A—C52—C52A | 161.30 (17) |
C33—C23—C24—C25 | −171.75 (16) | C46—C45—C52A—C47A | 24.97 (17) |
C30A—C23—C24—C25 | 5.29 (18) | C55—C45—C52A—C47A | −155.29 (14) |
C23—C24—C25—N32 | 84.75 (16) | C46—C45—C52A—C52 | −83.22 (17) |
C39—C24—C25—N32 | −88.66 (17) | C55—C45—C52A—C52 | 96.52 (17) |
C23—C24—C25—C25A | −31.61 (16) | C47B—C47A—C52A—C45 | −157.99 (13) |
C39—C24—C25—C25A | 154.98 (14) | C63—C47A—C52A—C45 | 75.88 (17) |
N32—C25—C25A—C25B | 32.49 (18) | C47—C47A—C52A—C45 | −41.51 (14) |
C24—C25—C25A—C25B | 149.30 (13) | C47B—C47A—C52A—C52 | −38.55 (15) |
N32—C25—C25A—C41 | 163.65 (12) | C63—C47A—C52A—C52 | −164.68 (13) |
C24—C25—C25A—C41 | −79.54 (15) | C47—C47A—C52A—C52 | 77.94 (13) |
N32—C25—C25A—C30A | −74.56 (14) | C51A—C52—C52A—C45 | 149.79 (13) |
C24—C25—C25A—C30A | 42.26 (13) | C53—C52—C52A—C45 | 36.38 (18) |
C41—C25A—C25B—C26 | −29.3 (2) | C51A—C52—C52A—C47A | 39.48 (15) |
C30A—C25A—C25B—C26 | −156.20 (16) | C53—C52—C52A—C47A | −73.93 (15) |
C25—C25A—C25B—C26 | 100.0 (2) | C51A—C52—C53—N54 | −53.32 (16) |
C41—C25A—C25B—C29A | 149.53 (14) | C52A—C52—C53—N54 | 55.67 (16) |
C30A—C25A—C25B—C29A | 22.64 (17) | C52—C53—N54—C66 | −174.61 (12) |
C25—C25A—C25B—C29A | −81.20 (17) | C52—C53—N54—C47 | −47.09 (17) |
C29A—C25B—C26—C27 | −1.6 (2) | C46—C47—N54—C66 | 74.48 (16) |
C25A—C25B—C26—C27 | 177.10 (15) | C47A—C47—N54—C66 | −174.19 (13) |
C43—O7—C27—C26 | 14.1 (2) | C46—C47—N54—C53 | −52.04 (17) |
C43—O7—C27—C28 | −165.90 (15) | C47A—C47—N54—C53 | 59.29 (16) |
C25B—C26—C27—O7 | −178.15 (15) | C46—C45—C55—C56 | −42.3 (3) |
C25B—C26—C27—C28 | 1.9 (2) | C52A—C45—C55—C56 | 138.03 (17) |
C42—O8—C28—C29 | 103.54 (18) | C46—C45—C55—C60 | 140.13 (19) |
C42—O8—C28—C27 | −81.8 (2) | C52A—C45—C55—C60 | −39.5 (2) |
O7—C27—C28—C29 | 179.56 (15) | C60—C55—C56—C57 | −1.1 (3) |
C26—C27—C28—C29 | −0.5 (2) | C45—C55—C56—C57 | −178.70 (16) |
O7—C27—C28—O8 | 5.0 (2) | C55—C56—C57—C58 | −0.7 (3) |
C26—C27—C28—O8 | −175.00 (14) | C56—C57—C58—C59 | 1.0 (3) |
O8—C28—C29—C29A | 173.37 (14) | C57—C58—C59—C60 | 0.5 (3) |
C27—C28—C29—C29A | −1.2 (2) | C58—C59—C60—C55 | −2.4 (3) |
C28—C29—C29A—C25B | 1.5 (2) | C56—C55—C60—C59 | 2.7 (2) |
C28—C29—C29A—C30 | 177.52 (16) | C45—C55—C60—C59 | −179.63 (15) |
C26—C25B—C29A—C29 | −0.1 (2) | C62—O10—C61—O9 | −4.4 (2) |
C25A—C25B—C29A—C29 | −179.06 (15) | C62—O10—C61—C46 | 175.83 (14) |
C26—C25B—C29A—C30 | −176.84 (14) | C45—C46—C61—O9 | 168.95 (17) |
C25A—C25B—C29A—C30 | 4.20 (18) | C47—C46—C61—O9 | −18.6 (2) |
C29—C29A—C30—C31 | −91.4 (2) | C45—C46—C61—O10 | −11.3 (3) |
C25B—C29A—C30—C31 | 84.96 (16) | C47—C46—C61—O10 | 161.13 (14) |
Funding information
The publication was prepared with the support of the RUDN University Program `5–100' and by the Russian Foundation for Basic Research (project No. 17-53-540001-Viet-a). This research is funded by the Vietnam National Foundation for Science and Technology Development (NAFOSTED) under grant No. 104.01–2015.27. Synchrotron radiation measurements were performed at the unique scientific facility Kurchatov Synchrotron Radiation Source supported by the Ministry of Education and Science of the Russian Federation (project code RFMEFI61917X0007).
References
Battye, T. G. G., Kontogiannis, L., Johnson, O., Powell, H. R. & Leslie, A. G. W. (2011). Acta Cryst. D67, 271–281. Web of Science CrossRef CAS IUCr Journals
Batzold, F. H., Covey, D. F. & Robinson, C. H. (1977). Cancer Treat. Rep. 61, 255–257. CAS PubMed
Batzold, F. H. & Robinson, C. H. (1975). J. Am. Chem. Soc. 97, 2576–2578. CrossRef PubMed CAS
Batzold, F. H. & Robinson, C. H. (1976). J. Org. Chem. 41, 313–317. CrossRef PubMed CAS
Bohlmann, F., Gupta, R. K., Jakupovic, J., King, R. M. & Robinson, H. (1980). Liebigs Ann. Chem. pp. 1904–1906. CrossRef
Doyle, R. A. (2011). Marccd software manual. Rayonix L. L. C., Evanston, IL 60201, USA.
Evans, P. (2006). Acta Cryst. D62, 72–82. Web of Science CrossRef CAS IUCr Journals
Jakupovic, J., Schmeda-Hirschmann, G., Schuster, A., Zdero, C., Bohlmann, F., King, R. M., Robinson, H. & Pickardt, J. (1985). Phytochemistry, 25, 145–158. CrossRef
Krause, N. & Hoffmann-Röder, A. (2004). Modern Allene Chemistry, Vol. 2, edited by N. Krause & A. S. K. Hashmi, pp. 997–1032. Weinheim: Wiley-VCH Verlag GmbH & Co.
Perscheid, M., Schollmeyer, D. & Nubbemeyer, U. (2011). Eur. J. Org. Chem. pp. 5250–5253. CSD CrossRef
Sashida, H. & Tsuchiya, T. (1984). Chem. Pharm. Bull. 32, 4600–4607. CrossRef CAS
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals
Voskressensky, L. G., Titov, A. A., Dzhankaziev, M. S., Borisova, T. N., Kobzev, M. S., Dorovatovskii, P. V., Khrustalev, V. N., Aksenov, A. V. & Varlamov, A. V. (2017). New J. Chem. 41, 1902–1904. CSD CrossRef CAS
Warning, U., Jakupovic, J., Bohlmann, F. & Jones, S. B. (1987). Liebigs Ann. Chem. pp. 467–468. CrossRef
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