research communications
Palladium(II) complexes of a bridging amine bis(phenolate) ligand featuring κ2 and κ3 coordination modes
aDonald J. Bettinger Department of Chemistry and Biochemistry, Ohio Northern University, 525 S. Main Street, Ada, Ohio 45810, USA, and bDepartment of Chemistry, Purdue University, 560 Oval Dr., West Lafayette, Indiana 47907, USA
*Correspondence e-mail: b-wile@onu.edu
Bidentate and tridentate coordination of a 2,4-di-tert-butyl-substituted bridging amine bis(phenolate) ligand to a palladium(II) center are observed within the same namely dichlorido({6,6′-[(ethane-1,2-diylbis(methylazanediyl)]bis(methylene)}bis(2,4-di-tert-butylphenol))palladium(II) chlorido(2,4-di-tert-butyl-6-{[(2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methyl](methyl)amino}ethyl)(methyl)amino]methyl}phenolato)palladium(II) methanol 1.685-solvate 0.315-hydrate, [PdCl2(C34H56N2O2)][PdCl(C34H55N2O2)]·1.685CH3OH·0.315H2O. Both complexes exhibit a square-planar geometry, with unbound phenol moieties participating in intermolecular hydrogen bonding with co-crystallized water and methanol. The presence of both κ2 and κ3 coordination modes arising from the same solution suggest a dynamic process in which phenol donors may coordinate or dissociate from the metal center, and offers insight into catalyst speciation throughout Pd-mediated processes. The contains dichlorido({6,6′-[(ethane-1,2-diylbis(methylazanediyl)]bis(methylene)}bis(2,4-di-tert-butylphenol))palladium(II), {(L2)PdCl2}, and chlorido(2,4-di-tert-butyl-6-{[(2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methyl](methyl)amino}ethyl)(methyl)amino]methyl}phenolato)palladium(II), {(L2X)PdCl}, molecules as well as fractional water and methanol solvent molecules.
Keywords: coordination compound; palladium(II); bidentate & tridentate coordination; amine bis(phenolate); crystal structure.
CCDC reference: 1940199
1. Chemical context
The activity of early transition-metal and rare-earth complexes of amine bis(phenolate) ligands for olefin (Tshuva et al., 2000) and cyclic ester polymerization (Carpentier, 2015) has been well documented. Several studies (Tshuva et al., 2001; Qian et al., 2011) demonstrated that the coordination mode and donor identity play a significant role in the activity of complexes derived from amine bis(phenolate) and related ligands. Amine bis(phenolate) complexes of iron have been employed as catalysts for cross-coupling (Chowdhury et al., 2008), polymerization (Allan et al., 2014) and CO2 conversion (Andrea et al., 2018) and as functional models for various non-heme metalloenzymes (Karimpour et al., 2013; Strautmann et al., 2011). While a relatively limited number of late transition-metal amine bis(phenolate) complexes have been employed as catalysts, nearly all have been observed to bind through both amine and both phenolate donor atoms to form κ4 complexes. Related complexes featuring κ2 or κ3 coordination modes may offer unique insight into catalyst identity for species that may not be directly observed.
Several related complexes feature ligands similar to these amine bis(phenolate) species bound in a κ3 fashion. Notably, Zn phenoxy diamine complexes are highly active catalysts for the polymerization of lactide. (Williams et al., 2003; Labourdette et al., 2009) Related modification to the amine bis(phenolate) framework generated `claw-type' κ3 Zn (Song et al., 2012; Wang et al., 2010) and Ti (Zhao et al., 2014) complexes that serve as competent polymerization catalysts. To our knowledge, only one report describes Pd complexes with amine bis(phenolate) ligands bound in a κ2 or κ3 coordination mode, in which both amine donors remain bound, and one phenolate donor may bind to the Pd center (Graziano et al., 2019). These species exhibit coordination behavior that varies with the steric parameters of the phenolate ortho and para substituents, with larger cumyl substituents favoring the formation of κ2 complexes. In this work, we describe diffraction data for a related Pd complex featuring the ligand {6,6′-[(ethane-1,2-diylbis(methylazanediyl)]bis(methylene)}bis(2,4-di-tert-butylphenol) bound in both κ2 or κ3 coordination modes within a single The presence of palladium(II) complexes displaying both κ2 and κ3 coordination modes arising from the same solution suggests a dynamic process in which phenol donors may coordinate or de-coordinate based on the electronic demands at the metal center.
2. Structural commentary
The ) consists of two distinct palladium(II) complexes of the amine bis(phenolate) {6,6′-[(ethane-1,2-diylbis(methylazanediyl)]bis(methylene)}bis(2,4-di-tert-butylphenol) and fractional quantities of methanol and water crystallization solvents. Both metal centers adopt similar distorted square-planar geometric arrangements, in which both nitrogen atoms of the ligand are bound to the Pd center to form a five-membered ring, and either one or two chlorine atoms are present to complete the coordination sphere depending on the coordination mode of the ligand. In both complexes, the N—Pd—N bond angle is similar to those observed for related amine bis(phenolate) Pd complexes (Graziano et al., 2019), as described in Table 1.
of the structure (Fig. 1Deprotonation and coordination of O1, presumably in the presence of water during crystallization, gives rise to the [(κ3-N,N,O)PdCl] complex. This complex is only slightly distorted from ideal square-planar geometry (τ4 parameter = 0.0823; Yang et al., 2007), and Pd1 lies 0.073 Å above the plane defined by O1/N1/N2/Cl1. The phenol ring containing O2 is disordered by rotation about the C20—C21 bond, such that in the minor component a close O2B—H2C⋯Cl1 interaction of ∼2.065 Å is observed (see Refinement section for details of the disorder). An additional close contact of ∼2.460 Å is observed between Cl1 and the O3—H bond of an unbound phenol from the neighboring [(κ2-N,N)PdCl2] complex.
The [(κ2-N,N)PdCl2] complex also exhibits only minor distortions from an ideal square-planar geometry (τ4 parameter = 0.0638; Yang et al., 2007), and Pd2 lies within (±0.001 Å) the plane defined by N3/N4/Cl2/Cl3. Both phenol rings in this complex are disordered by rotation about the C54—C55 bond and the C39—C40 bond, giving rise to a close O3B—H3D⋯Cl3 interaction of ∼2.12 Å and an O4B—H4D⋯Cl2 interaction of ∼2.05 Å, respectively.
Solution NMR data (see Synthesis and crystallization section) suggest that the conformations observed in the solid state are retained on the NMR timescale. Signals attributed to both the κ2 and κ3 complexes are observed, including signals attributed to the protonated phenol moieties. Signals attributed to the ligand methylene groups are rendered upon coordination of the distal donor atoms to the Pd center, while methylene units for unbound donors remain magnetically equivalent.
3. Supramolecular features
Hydrogen bonding (Table 2) is observed between phenol O2—H2, co-crystallized methanol solvent O5—H5, and O1 of a neighboring complex, forming a two-dimensional network in the bc plane between [(κ3-N,N,O)PdCl] subunits. Details of this interaction are illustrated in Fig. 2, which depicts the interaction between neighboring κ3 species, viewed along the a axis. Additional O—H⋯Cl interactions are observed between O3—H3 and Cl1, and O6—H6 and Cl3, though neither of these interactions forms an extended network. The interaction between O3—H3 and Cl1 is of interest as it is the only observed close contact between the κ2 and κ3 complexes within the This feature is absent in the minor component, in which the [(κ2-N,N)PdCl2] phenol hydroxy moiety O3B—H3D exhibits an intramolecular close contact with Cl3. Within the minor component, a related intramolecular close contact is observed between the remaining [(κ2-N,N)PdCl2] phenol hydroxy group O4B—H4D and Cl2.
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4. Synthesis and crystallization
Both species within this tert-butylphenol) ligand and bis(benzonitrile)dichloropalladium(II) in 5 mL of acetonitrile, using the method reported previously by Wile and co-workers (Graziano et al., 2019) as shown in Fig. 3. The titular compound was obtained as an orange solid (116 mg, 0.169 mmol, 67%). Single crystals suitable for X-ray diffraction studies were grown from a concentrated solution of the metal complex in methanol, layered with distilled water (∼10:1 v/v).
are generated upon combining equimolar quantities (0.254 mmol) of the {6,6′-[(ethane-1,2-diylbis(methylazanediyl)]bis(methylene)}bis(2,4-di-1H and 13C NMR spectra reveal signals attributed to both κ2 and κ3 Pd complexes in CDCl3 solution. The equilibrium, and the position of several signals shifts slightly when CD3OD is employed as the solvent for NMR characterization. The cleanest spectral data were obtained in CDCl3, and are reported below. Upon coordination, several methylene H's were rendered Spectroscopic assignments were confirmed through the use of 2D NMR (COSY, HSQC, HMBC) and polarization transfer (DEPT-135) experiments. 1H (CDCl3, 400.132 MHz) δ = 8.05 (s, 1H, OH), 7.51 (s, 1H, aryl C-H), 7.42 (m, 1H, aryl C-H), 7.36 (m, 2H, aryl C-H), 7.17–7.08 (m, 2H, aryl C-H), 6.83 (s, 1H, OH), 6.55 (m, 1H, aryl C-H), 4.64–4.50 (m, 2H, CH2), 3.79–3.65 (m, 1H, CH2), 3.59–3.48 (m, 1H, CH2), 3.35–3.20 (m, 3H), 3.00 (d, J = 13.6 Hz, 1H, CH2), 2.92–2.80 (m, 2H, CH2), 2.73–2.64 (m, 1H, CH2), 2.47 (s, 1H), 2.37–2.29 (m, 1H, CH2), 2.19–2.10 (m, 1H, CH2), 1.62 (s, 3H, CH3), 1.50 (s, 3H, CH3), 1.47–1.38 (m, 15H, CH3), 1.32 (s, 6H, CH3), 1.30 (s, 3H, CH3), 1.27 (s, 6H, CH3), 1.19 (s, 6H, CH3); 13C{1H} (CDCl3, 100.613 MHz) δ = 158.1 (4°), 153.3 (4°), 141.6 (4°), 139.6 (4°), 136.3 (4°), 129.0 (aryl C-H), 128.7 (4°), 125.5 (4°), 124.9 (4°), 124.0 (aryl C-H), 121.0 (4°), 117.6 (4°), 65.5 (CH2), 62.6 (CH2), 62.5 (CH2), 61.1 (CH2), 55.8 (CH2), 51.5, 41.7 (CH3), 35.4 (tBu 4°), 35.3 (tBu 4°), 35.0 (tBu 4°), 34.3 (tBu 4°), 34.1 (tBu 4°), 33.8 (tBu 4°), 31.6 (CH3), 30.2 (CH3), 30.1 (CH3), 29.9 (CH3), 29.6 (CH3). m.p. 435 K (decomp.)
5. Refinement
Crystal data, data collection and structure .
details are summarized in Table 3
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Water H atoms were restrained to have O—H bond lengths of 0.84 (2) Å, and 1.36 (2) Å H⋯H distances (DFIX, esd = 0.02 Å). All H atoms attached to carbon atoms as well as phenol and methanol hydroxyl hydrogens were positioned geometrically and constrained to ride on their parent atoms. C—H bond distances were constrained to 0.95 Å for aromatic C—H moieties, and to 0.99 and 0.98 Å for aliphatic CH2 and CH3 moieties, respectively. Phenol and methanol O—H distances were constrained to 0.84 Å. Methyl CH3 and hydroxyl H atoms were allowed to rotate but not to tip to best fit the experimental electron density. Uiso(H) values were set to a multiple of Ueq(C/O) with 1.5 for CH3, OH and water, and 1.2 for C—H, CH2, units, respectively.
Three of the four phenol hydroxyl groups are positionally disordered by rotation of the aromatic ring. For two of the three minor moieties, the O—C distance and the 1,3 O to C distances of the minor and major moieties were restrained to be similar (SADI command of SHELX, esd = 0.02 Å). Minor O atom O2B was constrained to have the same ADP as the C atom to which it is bonded. Two phenol H-atom positions were positionally restrained based on hydrogen-bonding considerations and to avoid close contacts to C-bound H atoms. Subject to these conditions, the occupancy rates of the major moieties refined to 0.917 (3), 0.857 (4) and 0.899 (4).
A tert-butyl group was refined as rotationally disordered. The two moieties were restrained to have similar geometries, the central C atoms to share one ADP, and the Uij components of ADPs were restrained to be similar (SIMU command of SHELX, esd = 0.01 Å2). Subject to these conditions the occupancy ratio refined to 0.716 (8):0.284 (8).
One solvate methanol molecule was refined as disordered over two orientations, and another to be disordered with a water molecule. The O—C distances of the major and minor methanol molecules were restrained to be similar (SADI, esd = 0.02 Å), and the Uij components of ADPs were restrained to be similar for the three methanol and the one water moiety (SIMU, esd = 0.01 Å2). Subject to these conditions the occupancy ratio refined to 0.685 (8):0.315 (8) for the methanol-to-water ratio, and 0.843 (4):0.157 (4) for the methanol-to-methanol ratio.
Supporting information
CCDC reference: 1940199
https://doi.org/10.1107/S2056989019010454/lh5914sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019010454/lh5914Isup2.hkl
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015), SHELXLE (Hübschle et al., 2011); molecular graphics: OLEX2 (Dolomanov, 2009), VESTA (Momma & Izumi, 2011); software used to prepare material for publication: publCIF (Westrip, 2010).[PdCl2(C34H56N2O2)][PdCl(C34H55N2O2)]·1.685CH4O·0.315H2O | F(000) = 3022 |
Mr = 1427.41 | Dx = 1.276 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.8843 (5) Å | Cell parameters from 9425 reflections |
b = 29.780 (1) Å | θ = 2.9–36.3° |
c = 16.6629 (6) Å | µ = 0.64 mm−1 |
β = 109.5536 (12)° | T = 100 K |
V = 7427.6 (4) Å3 | Plate, orange |
Z = 4 | 0.42 × 0.27 × 0.09 mm |
Bruker AXS D8 Quest CMOS diffractometer | 22272 independent reflections |
Radiation source: sealed tube X-ray source | 18396 reflections with I > 2σ(I) |
Triumph curved graphite crystal monochromator | Rint = 0.041 |
ω and phi scans | θmax = 30.5°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −22→22 |
Tmin = 0.656, Tmax = 0.747 | k = −42→35 |
87447 measured reflections | l = −18→23 |
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)] = 0.033 | Hydrogen site location: mixed |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0251P)2 + 7.3036P] where P = (Fo2 + 2Fc2)/3 |
22272 reflections | (Δ/σ)max = 0.006 |
900 parameters | Δρmax = 2.12 e Å−3 |
186 restraints | Δρmin = −0.92 e Å−3 |
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. Three of the four phenol hydroxyl groups are positionally disordered by rotation of the aromatic ring. For two of the three minor moieties the O-C distance and the 1,3 O to C distances of the minor and major moieties were restrained to be similar. Minor O atom O2B was constrained to have the same ADP as the C atom it is bonded to. Two phenol H atom positions were positionally restrained based on H-bonding considerations and to avoid close contacts to C bound H atoms. Subject to these conditions the occupancy rates of the major moieties refined to 0.917 (3), 0.857 (4) and 0.899 (4). A tert butyl group was refined as rotationally disordered. The two moieties were restrained to have similar geometries, the central C atoms to share one ADP, and Uij components of ADPs were restrained to be similar. Subject to these conditions the occupancy ratio refined to 0.716 (8) to 0.284 (8). One solvate methanol molecule was refined as disordered over two orientations, and another to be disordered with a water molecule. The O-C distance of the major and minor methanol molecules were restrained to be similar, and Uij components of ADPs were restrained to be similar for the three methanol and the one water moiety. Water H atoms were restrained to have O-H bond lengths of 0.84 (2) Angstroms, and 1.36 (2) Angstrom H···H distances. Subject to these conditions the occupancy ratio refined to 0.685 (8) to 0.315 (8) for the methanol to water ratio, and 0.843 (4) to 0.157 (4) for the methanol to methanol ratio. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.17953 (11) | 0.80735 (7) | 0.30459 (11) | 0.0194 (3) | |
H1A | 0.124296 | 0.825478 | 0.291263 | 0.023* | |
H1B | 0.164217 | 0.775609 | 0.310792 | 0.023* | |
C2 | 0.21826 (11) | 0.81161 (6) | 0.23312 (11) | 0.0186 (3) | |
H2A | 0.177086 | 0.797913 | 0.180441 | 0.022* | |
H2B | 0.225933 | 0.843696 | 0.221660 | 0.022* | |
C3 | 0.25578 (12) | 0.87326 (6) | 0.38525 (12) | 0.0189 (3) | |
H3A | 0.274902 | 0.882313 | 0.337477 | 0.028* | |
H3B | 0.300237 | 0.883118 | 0.438856 | 0.028* | |
H3C | 0.197988 | 0.887119 | 0.379094 | 0.028* | |
C4 | 0.29176 (14) | 0.73906 (6) | 0.23957 (13) | 0.0252 (4) | |
H4A | 0.259934 | 0.735029 | 0.178526 | 0.038* | |
H4B | 0.255957 | 0.726570 | 0.272035 | 0.038* | |
H4C | 0.349382 | 0.723493 | 0.255466 | 0.038* | |
C5 | 0.22069 (11) | 0.80871 (6) | 0.46069 (11) | 0.0175 (3) | |
H5A | 0.159724 | 0.819662 | 0.453394 | 0.021* | |
H5B | 0.219857 | 0.775496 | 0.462801 | 0.021* | |
C6 | 0.28488 (11) | 0.82650 (6) | 0.54299 (11) | 0.0172 (3) | |
C7 | 0.25435 (12) | 0.85501 (6) | 0.59361 (12) | 0.0203 (3) | |
H7 | 0.192537 | 0.862079 | 0.576693 | 0.024* | |
C8 | 0.31289 (13) | 0.87344 (6) | 0.66884 (12) | 0.0214 (4) | |
C9 | 0.40305 (12) | 0.86206 (6) | 0.69068 (11) | 0.0195 (3) | |
H9 | 0.443524 | 0.874213 | 0.741761 | 0.023* | |
C10 | 0.43751 (11) | 0.83389 (6) | 0.64207 (11) | 0.0176 (3) | |
C11 | 0.37664 (11) | 0.81525 (6) | 0.56647 (11) | 0.0165 (3) | |
C12 | 0.27754 (14) | 0.90546 (7) | 0.72233 (13) | 0.0278 (4) | |
C13 | 0.2301 (2) | 0.94537 (9) | 0.66700 (18) | 0.0493 (7) | |
H13A | 0.271220 | 0.960154 | 0.642776 | 0.074* | |
H13B | 0.211116 | 0.966851 | 0.702121 | 0.074* | |
H13C | 0.177649 | 0.934537 | 0.620839 | 0.074* | |
C14 | 0.2107 (2) | 0.88091 (10) | 0.75446 (19) | 0.0514 (7) | |
H14A | 0.162850 | 0.868296 | 0.705981 | 0.077* | |
H14B | 0.185163 | 0.902034 | 0.785119 | 0.077* | |
H14C | 0.241205 | 0.856620 | 0.792902 | 0.077* | |
C15 | 0.35247 (18) | 0.92506 (9) | 0.79799 (15) | 0.0401 (6) | |
H15A | 0.394948 | 0.941150 | 0.777254 | 0.060* | |
H15B | 0.383447 | 0.900697 | 0.835955 | 0.060* | |
H15C | 0.326986 | 0.945892 | 0.829225 | 0.060* | |
C16 | 0.53860 (11) | 0.82428 (6) | 0.66905 (11) | 0.0190 (3) | |
C17 | 0.57415 (12) | 0.84092 (7) | 0.59878 (12) | 0.0238 (4) | |
H17A | 0.544245 | 0.824557 | 0.545847 | 0.036* | |
H17B | 0.638691 | 0.835647 | 0.616394 | 0.036* | |
H17C | 0.562100 | 0.873116 | 0.589428 | 0.036* | |
C18 | 0.55738 (13) | 0.77371 (7) | 0.68368 (13) | 0.0239 (4) | |
H18A | 0.525242 | 0.757245 | 0.631485 | 0.036* | |
H18B | 0.537201 | 0.763440 | 0.730096 | 0.036* | |
H18C | 0.621664 | 0.768247 | 0.698789 | 0.036* | |
C19 | 0.59150 (13) | 0.84892 (8) | 0.75145 (13) | 0.0289 (4) | |
H19A | 0.655086 | 0.841619 | 0.766644 | 0.043* | |
H19B | 0.569987 | 0.839469 | 0.797507 | 0.043* | |
H19C | 0.583179 | 0.881385 | 0.742794 | 0.043* | |
C20 | 0.36366 (12) | 0.80514 (6) | 0.20834 (11) | 0.0194 (3) | |
H20A | 0.422187 | 0.789679 | 0.228461 | 0.023* | |
H20B | 0.334165 | 0.797097 | 0.147732 | 0.023* | |
C21 | 0.37937 (12) | 0.85519 (6) | 0.21469 (11) | 0.0179 (3) | |
C22 | 0.44292 (12) | 0.87334 (7) | 0.28698 (11) | 0.0201 (3) | |
H22 | 0.476336 | 0.853829 | 0.331313 | 0.024* | 0.917 (3) |
C23 | 0.45843 (12) | 0.91936 (7) | 0.29554 (12) | 0.0216 (4) | |
C24 | 0.40753 (12) | 0.94681 (7) | 0.22901 (12) | 0.0224 (4) | |
H24 | 0.416930 | 0.978327 | 0.234504 | 0.027* | |
C25 | 0.34364 (12) | 0.93061 (7) | 0.15490 (12) | 0.0209 (4) | |
C26 | 0.33134 (12) | 0.88384 (7) | 0.14817 (11) | 0.0213 (4) | |
H26 | 0.289926 | 0.871434 | 0.097885 | 0.026* | 0.083 (3) |
C27 | 0.52639 (14) | 0.93896 (7) | 0.37683 (13) | 0.0274 (4) | |
C28 | 0.5518 (2) | 0.98740 (10) | 0.36385 (17) | 0.0528 (8) | |
H28A | 0.577123 | 0.988309 | 0.317726 | 0.079* | |
H28B | 0.596057 | 0.998444 | 0.416539 | 0.079* | |
H28C | 0.498403 | 1.006414 | 0.348971 | 0.079* | |
C29 | 0.61076 (15) | 0.90945 (10) | 0.40685 (17) | 0.0475 (7) | |
H29A | 0.594515 | 0.879079 | 0.418959 | 0.071* | |
H29B | 0.653492 | 0.922361 | 0.458601 | 0.071* | |
H29C | 0.637970 | 0.908136 | 0.362089 | 0.071* | |
C30 | 0.48404 (16) | 0.93941 (8) | 0.44706 (13) | 0.0320 (5) | |
H30A | 0.431519 | 0.959059 | 0.430062 | 0.048* | |
H30B | 0.527586 | 0.950598 | 0.500060 | 0.048* | |
H30C | 0.465948 | 0.908872 | 0.455959 | 0.048* | |
C31 | 0.28669 (13) | 0.96291 (7) | 0.08547 (13) | 0.0235 (4) | |
C32 | 0.18826 (14) | 0.95698 (8) | 0.07806 (15) | 0.0310 (4) | |
H32A | 0.151257 | 0.978120 | 0.035828 | 0.047* | |
H32B | 0.181486 | 0.962839 | 0.133454 | 0.047* | |
H32C | 0.169280 | 0.926184 | 0.060189 | 0.047* | |
C33 | 0.29709 (16) | 0.95343 (8) | −0.00108 (13) | 0.0342 (5) | |
H33A | 0.257826 | 0.973494 | −0.044085 | 0.051* | |
H33B | 0.280830 | 0.922156 | −0.017292 | 0.051* | |
H33C | 0.359260 | 0.958571 | 0.002776 | 0.051* | |
C34 | 0.31216 (15) | 1.01223 (7) | 0.10743 (15) | 0.0335 (5) | |
H34A | 0.274848 | 1.031531 | 0.061685 | 0.050* | |
H34B | 0.375168 | 1.016687 | 0.113673 | 0.050* | |
H34C | 0.302732 | 1.019955 | 0.160962 | 0.050* | |
C35 | 0.82670 (13) | 0.78738 (7) | 0.62727 (12) | 0.0227 (4) | |
H35A | 0.824884 | 0.784692 | 0.685884 | 0.027* | |
H35B | 0.814599 | 0.819066 | 0.609060 | 0.027* | |
C36 | 0.75680 (12) | 0.75753 (6) | 0.56829 (12) | 0.0214 (4) | |
H36A | 0.763320 | 0.726637 | 0.591504 | 0.026* | |
H36B | 0.696603 | 0.768609 | 0.563713 | 0.026* | |
C37 | 0.94963 (15) | 0.73294 (7) | 0.67850 (12) | 0.0260 (4) | |
H37A | 0.906169 | 0.708645 | 0.657586 | 0.039* | |
H37B | 0.956574 | 0.739453 | 0.738028 | 0.039* | |
H37C | 1.007331 | 0.723757 | 0.674484 | 0.039* | |
C38 | 0.72900 (13) | 0.79913 (7) | 0.43422 (14) | 0.0276 (4) | |
H38A | 0.733626 | 0.797676 | 0.377086 | 0.041* | |
H38B | 0.762670 | 0.825093 | 0.464726 | 0.041* | |
H38C | 0.666107 | 0.802153 | 0.429580 | 0.041* | |
C39 | 0.98438 (13) | 0.81102 (7) | 0.66335 (12) | 0.0242 (4) | |
H39A | 0.994263 | 0.813458 | 0.725091 | 0.029* | |
H39B | 1.042106 | 0.803016 | 0.656532 | 0.029* | |
C40 | 0.95395 (12) | 0.85599 (7) | 0.62173 (12) | 0.0223 (4) | |
C41 | 0.96205 (12) | 0.86495 (7) | 0.54242 (12) | 0.0216 (4) | |
H41 | 0.992642 | 0.844110 | 0.518897 | 0.026* | 0.899 (4) |
C42 | 0.92636 (12) | 0.90370 (6) | 0.49693 (12) | 0.0206 (3) | |
C43 | 0.88280 (12) | 0.93363 (6) | 0.53447 (12) | 0.0220 (4) | |
H43 | 0.856925 | 0.959867 | 0.503581 | 0.026* | |
C44 | 0.87513 (12) | 0.92721 (6) | 0.61466 (12) | 0.0230 (4) | |
C45 | 0.91311 (13) | 0.88776 (7) | 0.65884 (12) | 0.0247 (4) | |
H45 | 0.911017 | 0.882651 | 0.714420 | 0.030* | 0.101 (4) |
C46 | 0.9314 (4) | 0.9110 (2) | 0.4058 (6) | 0.0242 (7) | 0.716 (8) |
C47 | 1.0265 (4) | 0.9038 (3) | 0.4074 (6) | 0.083 (3) | 0.716 (8) |
H47A | 1.029465 | 0.908772 | 0.350239 | 0.125* | 0.716 (8) |
H47B | 1.045109 | 0.872976 | 0.425470 | 0.125* | 0.716 (8) |
H47C | 1.066331 | 0.924959 | 0.447385 | 0.125* | 0.716 (8) |
C48 | 0.9003 (4) | 0.95804 (12) | 0.3720 (3) | 0.0453 (12) | 0.716 (8) |
H48A | 0.905189 | 0.961543 | 0.315213 | 0.068* | 0.716 (8) |
H48B | 0.937886 | 0.980505 | 0.410573 | 0.068* | 0.716 (8) |
H48C | 0.837993 | 0.962226 | 0.368466 | 0.068* | 0.716 (8) |
C49 | 0.8698 (3) | 0.87713 (15) | 0.3444 (2) | 0.0431 (11) | 0.716 (8) |
H49A | 0.808235 | 0.881608 | 0.343165 | 0.065* | 0.716 (8) |
H49B | 0.889015 | 0.846534 | 0.363541 | 0.065* | 0.716 (8) |
H49C | 0.872653 | 0.881615 | 0.287067 | 0.065* | 0.716 (8) |
C46B | 0.9326 (11) | 0.9135 (5) | 0.4130 (16) | 0.0242 (7) | 0.284 (8) |
C47B | 1.0007 (11) | 0.8840 (6) | 0.3924 (10) | 0.060 (5) | 0.284 (8) |
H47D | 1.005037 | 0.892881 | 0.337305 | 0.090* | 0.284 (8) |
H47E | 0.981869 | 0.852516 | 0.389804 | 0.090* | 0.284 (8) |
H47F | 1.059127 | 0.887487 | 0.436844 | 0.090* | 0.284 (8) |
C48B | 0.9648 (9) | 0.9616 (3) | 0.4077 (8) | 0.049 (3) | 0.284 (8) |
H48D | 0.971671 | 0.966356 | 0.352024 | 0.073* | 0.284 (8) |
H48E | 1.022428 | 0.966322 | 0.452747 | 0.073* | 0.284 (8) |
H48F | 0.920922 | 0.982931 | 0.415005 | 0.073* | 0.284 (8) |
C49B | 0.8410 (6) | 0.9070 (6) | 0.3445 (6) | 0.056 (4) | 0.284 (8) |
H49D | 0.821845 | 0.875775 | 0.345083 | 0.084* | 0.284 (8) |
H49E | 0.845064 | 0.914116 | 0.288509 | 0.084* | 0.284 (8) |
H49F | 0.797498 | 0.927024 | 0.356195 | 0.084* | 0.284 (8) |
C50 | 0.82772 (15) | 0.96168 (7) | 0.65348 (14) | 0.0302 (4) | |
C51 | 0.74905 (17) | 0.93991 (9) | 0.67292 (17) | 0.0415 (6) | |
H51A | 0.707962 | 0.926466 | 0.620829 | 0.062* | |
H51B | 0.717428 | 0.962812 | 0.694078 | 0.062* | |
H51C | 0.771552 | 0.916550 | 0.716264 | 0.062* | |
C52 | 0.78897 (16) | 1.00097 (8) | 0.59236 (17) | 0.0397 (6) | |
H52A | 0.745544 | 0.989460 | 0.539595 | 0.060* | |
H52B | 0.837358 | 1.016372 | 0.579297 | 0.060* | |
H52C | 0.759325 | 1.022123 | 0.619244 | 0.060* | |
C53 | 0.89511 (18) | 0.98139 (9) | 0.73532 (16) | 0.0434 (6) | |
H53A | 0.945630 | 0.994493 | 0.722265 | 0.065* | |
H53B | 0.916729 | 0.957504 | 0.777697 | 0.065* | |
H53C | 0.865827 | 1.004723 | 0.758047 | 0.065* | |
C54 | 0.71609 (11) | 0.71773 (6) | 0.43015 (12) | 0.0199 (3) | |
H54A | 0.651256 | 0.724189 | 0.411538 | 0.024* | |
H54B | 0.733107 | 0.714500 | 0.378453 | 0.024* | |
C55 | 0.73381 (11) | 0.67400 (6) | 0.47843 (11) | 0.0181 (3) | |
C56 | 0.81404 (11) | 0.65147 (6) | 0.49064 (11) | 0.0190 (3) | |
H56 | 0.853784 | 0.662458 | 0.463438 | 0.023* | 0.857 (4) |
C57 | 0.83762 (12) | 0.61328 (6) | 0.54161 (11) | 0.0192 (3) | |
C58 | 0.77628 (13) | 0.59762 (6) | 0.57860 (12) | 0.0223 (4) | |
H58 | 0.791871 | 0.571904 | 0.614255 | 0.027* | |
C59 | 0.69358 (12) | 0.61752 (7) | 0.56624 (12) | 0.0219 (4) | |
C60 | 0.67343 (11) | 0.65639 (7) | 0.51527 (12) | 0.0206 (3) | |
H60 | 0.617740 | 0.671004 | 0.505629 | 0.025* | 0.143 (4) |
C61 | 0.92834 (13) | 0.59069 (7) | 0.55567 (13) | 0.0244 (4) | |
C62 | 0.94060 (16) | 0.54802 (8) | 0.60966 (15) | 0.0349 (5) | |
H62A | 0.892231 | 0.526887 | 0.582237 | 0.052* | |
H62B | 0.939272 | 0.555719 | 0.666405 | 0.052* | |
H62C | 0.998155 | 0.534161 | 0.614894 | 0.052* | |
C63 | 0.93679 (14) | 0.57830 (8) | 0.46884 (14) | 0.0304 (4) | |
H63A | 0.887427 | 0.558430 | 0.437847 | 0.046* | |
H63B | 0.993754 | 0.562897 | 0.477896 | 0.046* | |
H63C | 0.934557 | 0.605684 | 0.435584 | 0.046* | |
C64 | 1.00323 (13) | 0.62374 (8) | 0.60294 (15) | 0.0335 (5) | |
H64A | 1.061471 | 0.609641 | 0.612221 | 0.050* | |
H64B | 0.997492 | 0.631604 | 0.657991 | 0.050* | |
H64C | 0.998313 | 0.650978 | 0.568673 | 0.050* | |
C65 | 0.62817 (14) | 0.59830 (8) | 0.60747 (15) | 0.0327 (5) | |
C66 | 0.61091 (16) | 0.63295 (9) | 0.66877 (16) | 0.0403 (6) | |
H66A | 0.585029 | 0.660190 | 0.637104 | 0.060* | |
H66B | 0.667416 | 0.640399 | 0.713348 | 0.060* | |
H66C | 0.569293 | 0.620302 | 0.694870 | 0.060* | |
C67 | 0.54135 (17) | 0.58412 (11) | 0.5376 (2) | 0.0559 (8) | |
H67A | 0.513127 | 0.610499 | 0.504278 | 0.084* | |
H67B | 0.500538 | 0.570766 | 0.563928 | 0.084* | |
H67C | 0.555000 | 0.562032 | 0.500144 | 0.084* | |
C68 | 0.6653 (2) | 0.55572 (9) | 0.66041 (19) | 0.0482 (7) | |
H68A | 0.677181 | 0.532695 | 0.623551 | 0.072* | |
H68B | 0.621436 | 0.544351 | 0.685028 | 0.072* | |
H68C | 0.720940 | 0.563107 | 0.706248 | 0.072* | |
O5 | 0.3231 (2) | 0.70311 (9) | 0.50018 (17) | 0.0253 (7) | 0.685 (8) |
H5 | 0.347038 | 0.728568 | 0.510765 | 0.038* | 0.685 (8) |
C69 | 0.3784 (3) | 0.67414 (13) | 0.4738 (3) | 0.0462 (12) | 0.685 (8) |
H69A | 0.387186 | 0.686296 | 0.422488 | 0.069* | 0.685 (8) |
H69B | 0.350314 | 0.644488 | 0.461162 | 0.069* | 0.685 (8) |
H69C | 0.436337 | 0.671417 | 0.519210 | 0.069* | 0.685 (8) |
O5B | 0.3750 (8) | 0.6952 (2) | 0.5134 (4) | 0.042 (2) | 0.315 (8) |
H5C | 0.380 (7) | 0.7231 (9) | 0.520 (6) | 0.063* | 0.315 (8) |
H5D | 0.341 (7) | 0.690 (3) | 0.462 (3) | 0.063* | 0.315 (8) |
O6 | 1.02032 (15) | 0.66923 (8) | 0.36487 (12) | 0.0432 (6) | 0.843 (4) |
H6 | 1.001717 | 0.691429 | 0.385152 | 0.065* | 0.843 (4) |
C70 | 1.1050 (3) | 0.65658 (16) | 0.4205 (2) | 0.0439 (9) | 0.843 (4) |
H70A | 1.149634 | 0.678422 | 0.416707 | 0.066* | 0.843 (4) |
H70B | 1.120249 | 0.626776 | 0.404579 | 0.066* | 0.843 (4) |
H70C | 1.104027 | 0.655737 | 0.478980 | 0.066* | 0.843 (4) |
O6B | 1.1055 (10) | 0.7095 (5) | 0.3721 (9) | 0.063 (4) | 0.157 (4) |
H6B | 1.082514 | 0.725418 | 0.400806 | 0.095* | 0.157 (4) |
C70B | 1.104 (3) | 0.6652 (8) | 0.3948 (17) | 0.065 (6) | 0.157 (4) |
H70D | 1.116875 | 0.663148 | 0.456460 | 0.097* | 0.157 (4) |
H70E | 1.148844 | 0.648392 | 0.378888 | 0.097* | 0.157 (4) |
H70F | 1.044521 | 0.652638 | 0.365208 | 0.097* | 0.157 (4) |
N1 | 0.24699 (9) | 0.82353 (5) | 0.38574 (9) | 0.0144 (3) | |
N2 | 0.30708 (9) | 0.78810 (5) | 0.25896 (9) | 0.0153 (3) | |
N3 | 0.91741 (10) | 0.77394 (5) | 0.62590 (9) | 0.0177 (3) | |
N4 | 0.76653 (9) | 0.75710 (5) | 0.48193 (9) | 0.0172 (3) | |
O1 | 0.40507 (8) | 0.78699 (4) | 0.51791 (7) | 0.0172 (2) | |
O2 | 0.26805 (12) | 0.86608 (5) | 0.07650 (10) | 0.0330 (4) | 0.917 (3) |
H2 | 0.290674 | 0.844771 | 0.057669 | 0.049* | 0.917 (3) |
O2B | 0.5034 (9) | 0.8514 (5) | 0.3518 (8) | 0.0201 (3) | 0.083 (3) |
H2C | 0.486603 | 0.824743 | 0.353287 | 0.030* | 0.083 (3) |
O3 | 0.59302 (10) | 0.67610 (6) | 0.50671 (11) | 0.0295 (5) | 0.857 (4) |
H3 | 0.575190 | 0.690570 | 0.460818 | 0.044* | 0.857 (4) |
O3B | 0.8753 (6) | 0.6616 (3) | 0.4513 (7) | 0.024 (3) | 0.143 (4) |
H3D | 0.871900 | 0.689051 | 0.438845 | 0.036* | 0.143 (4) |
O4 | 0.90424 (13) | 0.88163 (6) | 0.73783 (10) | 0.0337 (5) | 0.899 (4) |
H4 | 0.943603 | 0.863677 | 0.766568 | 0.051* | 0.899 (4) |
O4B | 1.0122 (8) | 0.8408 (4) | 0.5013 (7) | 0.022 (4) | 0.101 (4) |
H4D | 1.041665 | 0.820583 | 0.533947 | 0.033* | 0.101 (4) |
Pd1 | 0.36273 (2) | 0.79241 (2) | 0.39043 (2) | 0.01248 (3) | |
Pd2 | 0.90248 (2) | 0.75700 (2) | 0.50140 (2) | 0.01722 (3) | |
Cl1 | 0.49514 (3) | 0.75869 (2) | 0.39289 (3) | 0.02383 (9) | |
Cl2 | 1.05553 (3) | 0.75220 (2) | 0.52937 (3) | 0.02905 (11) | |
Cl3 | 0.87855 (4) | 0.74325 (2) | 0.35902 (3) | 0.03647 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0134 (7) | 0.0250 (9) | 0.0175 (8) | −0.0010 (7) | 0.0021 (6) | −0.0029 (7) |
C2 | 0.0145 (7) | 0.0250 (9) | 0.0142 (8) | 0.0016 (7) | 0.0021 (6) | −0.0014 (7) |
C3 | 0.0197 (8) | 0.0139 (8) | 0.0249 (9) | 0.0018 (7) | 0.0096 (7) | 0.0010 (6) |
C4 | 0.0309 (10) | 0.0181 (9) | 0.0260 (10) | −0.0027 (8) | 0.0089 (8) | −0.0083 (7) |
C5 | 0.0146 (7) | 0.0226 (8) | 0.0172 (8) | −0.0009 (7) | 0.0077 (6) | 0.0005 (6) |
C6 | 0.0163 (7) | 0.0203 (8) | 0.0161 (8) | 0.0004 (7) | 0.0069 (6) | 0.0010 (6) |
C7 | 0.0205 (8) | 0.0225 (9) | 0.0211 (8) | 0.0021 (7) | 0.0111 (7) | 0.0003 (7) |
C8 | 0.0271 (9) | 0.0227 (9) | 0.0182 (8) | 0.0001 (7) | 0.0125 (7) | −0.0017 (7) |
C9 | 0.0240 (8) | 0.0212 (8) | 0.0138 (8) | −0.0039 (7) | 0.0072 (6) | −0.0014 (6) |
C10 | 0.0188 (7) | 0.0206 (8) | 0.0141 (8) | −0.0004 (7) | 0.0062 (6) | 0.0018 (6) |
C11 | 0.0192 (7) | 0.0180 (8) | 0.0143 (7) | 0.0009 (7) | 0.0081 (6) | 0.0019 (6) |
C12 | 0.0350 (10) | 0.0260 (10) | 0.0278 (10) | 0.0001 (9) | 0.0177 (9) | −0.0087 (8) |
C13 | 0.0653 (18) | 0.0386 (14) | 0.0454 (15) | 0.0174 (13) | 0.0202 (13) | −0.0054 (12) |
C14 | 0.0624 (17) | 0.0483 (16) | 0.0654 (18) | −0.0167 (14) | 0.0506 (15) | −0.0241 (14) |
C15 | 0.0536 (14) | 0.0372 (13) | 0.0344 (12) | −0.0036 (11) | 0.0212 (11) | −0.0139 (10) |
C16 | 0.0166 (7) | 0.0236 (9) | 0.0152 (8) | −0.0016 (7) | 0.0035 (6) | 0.0024 (6) |
C17 | 0.0196 (8) | 0.0282 (10) | 0.0242 (9) | −0.0026 (8) | 0.0082 (7) | 0.0057 (8) |
C18 | 0.0211 (8) | 0.0255 (9) | 0.0235 (9) | 0.0006 (8) | 0.0052 (7) | 0.0051 (7) |
C19 | 0.0241 (9) | 0.0357 (11) | 0.0210 (9) | −0.0026 (8) | −0.0002 (7) | −0.0032 (8) |
C20 | 0.0224 (8) | 0.0240 (9) | 0.0139 (8) | 0.0036 (7) | 0.0090 (6) | −0.0010 (6) |
C21 | 0.0202 (8) | 0.0204 (8) | 0.0158 (8) | 0.0021 (7) | 0.0095 (6) | 0.0029 (6) |
C22 | 0.0193 (8) | 0.0277 (9) | 0.0151 (8) | 0.0027 (7) | 0.0079 (6) | 0.0033 (7) |
C23 | 0.0213 (8) | 0.0276 (10) | 0.0185 (8) | −0.0027 (7) | 0.0099 (7) | 0.0000 (7) |
C24 | 0.0246 (9) | 0.0232 (9) | 0.0227 (9) | 0.0002 (7) | 0.0125 (7) | 0.0018 (7) |
C25 | 0.0217 (8) | 0.0244 (9) | 0.0194 (8) | 0.0047 (7) | 0.0104 (7) | 0.0042 (7) |
C26 | 0.0218 (8) | 0.0266 (9) | 0.0155 (8) | 0.0042 (7) | 0.0065 (7) | 0.0019 (7) |
C27 | 0.0283 (9) | 0.0310 (11) | 0.0220 (9) | −0.0034 (8) | 0.0072 (8) | −0.0010 (8) |
C28 | 0.0636 (17) | 0.0521 (16) | 0.0329 (13) | −0.0340 (14) | 0.0032 (12) | 0.0030 (12) |
C29 | 0.0257 (10) | 0.0689 (19) | 0.0408 (14) | 0.0030 (12) | 0.0016 (10) | −0.0218 (13) |
C30 | 0.0417 (12) | 0.0330 (11) | 0.0198 (9) | 0.0031 (10) | 0.0085 (9) | −0.0029 (8) |
C31 | 0.0241 (9) | 0.0231 (9) | 0.0247 (9) | 0.0063 (8) | 0.0102 (7) | 0.0061 (7) |
C32 | 0.0258 (9) | 0.0290 (11) | 0.0387 (12) | 0.0067 (8) | 0.0113 (9) | 0.0069 (9) |
C33 | 0.0408 (12) | 0.0397 (12) | 0.0238 (10) | 0.0187 (10) | 0.0129 (9) | 0.0132 (9) |
C34 | 0.0360 (11) | 0.0259 (10) | 0.0376 (12) | 0.0029 (9) | 0.0109 (9) | 0.0079 (9) |
C35 | 0.0272 (9) | 0.0251 (9) | 0.0226 (9) | 0.0019 (8) | 0.0172 (7) | 0.0005 (7) |
C36 | 0.0222 (8) | 0.0219 (9) | 0.0272 (9) | 0.0018 (7) | 0.0176 (7) | 0.0017 (7) |
C37 | 0.0385 (11) | 0.0247 (10) | 0.0163 (9) | 0.0086 (8) | 0.0115 (8) | 0.0048 (7) |
C38 | 0.0190 (8) | 0.0242 (10) | 0.0375 (11) | 0.0018 (7) | 0.0065 (8) | 0.0133 (8) |
C39 | 0.0252 (9) | 0.0256 (9) | 0.0168 (8) | 0.0005 (8) | 0.0005 (7) | −0.0001 (7) |
C40 | 0.0208 (8) | 0.0230 (9) | 0.0192 (9) | −0.0031 (7) | 0.0015 (7) | −0.0006 (7) |
C41 | 0.0182 (8) | 0.0226 (9) | 0.0228 (9) | 0.0006 (7) | 0.0055 (7) | −0.0012 (7) |
C42 | 0.0178 (8) | 0.0222 (9) | 0.0217 (9) | −0.0028 (7) | 0.0063 (7) | −0.0009 (7) |
C43 | 0.0195 (8) | 0.0187 (8) | 0.0262 (9) | −0.0032 (7) | 0.0056 (7) | −0.0029 (7) |
C44 | 0.0221 (8) | 0.0213 (9) | 0.0248 (9) | −0.0063 (7) | 0.0069 (7) | −0.0085 (7) |
C45 | 0.0270 (9) | 0.0259 (10) | 0.0189 (9) | −0.0061 (8) | 0.0047 (7) | −0.0055 (7) |
C46 | 0.0223 (9) | 0.0295 (12) | 0.0238 (19) | 0.0036 (9) | 0.0115 (9) | 0.0053 (10) |
C47 | 0.030 (2) | 0.177 (10) | 0.052 (4) | 0.025 (4) | 0.026 (2) | 0.043 (5) |
C48 | 0.076 (3) | 0.0276 (17) | 0.037 (2) | 0.0010 (19) | 0.025 (2) | 0.0098 (14) |
C49 | 0.065 (3) | 0.041 (2) | 0.0230 (16) | −0.007 (2) | 0.0152 (16) | −0.0002 (15) |
C46B | 0.0223 (9) | 0.0295 (12) | 0.0238 (19) | 0.0036 (9) | 0.0115 (9) | 0.0053 (10) |
C47B | 0.073 (11) | 0.086 (10) | 0.033 (6) | 0.066 (9) | 0.035 (8) | 0.035 (7) |
C48B | 0.070 (8) | 0.035 (5) | 0.059 (7) | −0.011 (5) | 0.045 (6) | 0.005 (4) |
C49B | 0.035 (5) | 0.114 (12) | 0.020 (4) | −0.021 (6) | 0.010 (4) | 0.007 (5) |
C50 | 0.0325 (10) | 0.0257 (10) | 0.0349 (11) | −0.0077 (9) | 0.0146 (9) | −0.0142 (9) |
C51 | 0.0402 (12) | 0.0415 (14) | 0.0515 (15) | −0.0076 (11) | 0.0270 (12) | −0.0154 (11) |
C52 | 0.0388 (12) | 0.0252 (11) | 0.0575 (16) | 0.0020 (10) | 0.0193 (11) | −0.0127 (10) |
C53 | 0.0499 (14) | 0.0412 (14) | 0.0401 (14) | −0.0137 (12) | 0.0164 (11) | −0.0247 (11) |
C54 | 0.0139 (7) | 0.0249 (9) | 0.0192 (8) | 0.0001 (7) | 0.0032 (6) | 0.0056 (7) |
C55 | 0.0139 (7) | 0.0220 (8) | 0.0165 (8) | −0.0012 (7) | 0.0027 (6) | 0.0019 (6) |
C56 | 0.0166 (7) | 0.0227 (9) | 0.0169 (8) | −0.0015 (7) | 0.0043 (6) | −0.0008 (7) |
C57 | 0.0185 (8) | 0.0197 (8) | 0.0164 (8) | 0.0005 (7) | 0.0019 (6) | −0.0023 (6) |
C58 | 0.0257 (9) | 0.0195 (8) | 0.0196 (9) | −0.0019 (7) | 0.0049 (7) | 0.0011 (7) |
C59 | 0.0195 (8) | 0.0242 (9) | 0.0212 (9) | −0.0050 (7) | 0.0057 (7) | 0.0004 (7) |
C60 | 0.0137 (7) | 0.0262 (9) | 0.0198 (8) | −0.0008 (7) | 0.0029 (6) | 0.0022 (7) |
C61 | 0.0218 (8) | 0.0233 (9) | 0.0247 (9) | 0.0042 (7) | 0.0035 (7) | −0.0028 (7) |
C62 | 0.0362 (11) | 0.0291 (11) | 0.0325 (12) | 0.0114 (9) | 0.0025 (9) | 0.0028 (9) |
C63 | 0.0256 (9) | 0.0338 (11) | 0.0305 (11) | 0.0042 (9) | 0.0078 (8) | −0.0080 (9) |
C64 | 0.0188 (9) | 0.0328 (11) | 0.0414 (13) | 0.0047 (8) | 0.0002 (8) | −0.0139 (9) |
C65 | 0.0266 (10) | 0.0385 (12) | 0.0348 (11) | −0.0073 (9) | 0.0127 (9) | 0.0074 (9) |
C66 | 0.0344 (11) | 0.0534 (15) | 0.0414 (13) | 0.0084 (11) | 0.0236 (10) | 0.0136 (11) |
C67 | 0.0356 (13) | 0.068 (2) | 0.0628 (19) | −0.0263 (14) | 0.0140 (13) | 0.0035 (15) |
C68 | 0.0594 (16) | 0.0381 (14) | 0.0593 (17) | −0.0032 (13) | 0.0362 (14) | 0.0174 (12) |
O5 | 0.0307 (15) | 0.0231 (12) | 0.0259 (12) | −0.0020 (11) | 0.0144 (11) | −0.0014 (9) |
C69 | 0.055 (2) | 0.0218 (17) | 0.081 (3) | −0.0019 (16) | 0.048 (2) | −0.003 (2) |
O5B | 0.076 (6) | 0.021 (3) | 0.038 (3) | −0.006 (3) | 0.030 (4) | 0.003 (2) |
O6 | 0.0493 (13) | 0.0515 (14) | 0.0208 (10) | 0.0174 (10) | 0.0011 (9) | −0.0052 (8) |
C70 | 0.0377 (15) | 0.064 (2) | 0.033 (2) | 0.0077 (17) | 0.0156 (16) | −0.0036 (16) |
O6B | 0.079 (8) | 0.072 (8) | 0.053 (7) | −0.012 (7) | 0.041 (6) | −0.011 (6) |
C70B | 0.078 (10) | 0.083 (10) | 0.039 (10) | 0.007 (9) | 0.027 (9) | −0.005 (9) |
N1 | 0.0122 (6) | 0.0162 (7) | 0.0139 (6) | 0.0005 (5) | 0.0033 (5) | −0.0014 (5) |
N2 | 0.0167 (6) | 0.0152 (7) | 0.0141 (6) | 0.0005 (5) | 0.0051 (5) | −0.0017 (5) |
N3 | 0.0210 (7) | 0.0190 (7) | 0.0146 (7) | 0.0020 (6) | 0.0077 (6) | 0.0015 (5) |
N4 | 0.0145 (6) | 0.0208 (7) | 0.0171 (7) | 0.0022 (6) | 0.0063 (5) | 0.0058 (6) |
O1 | 0.0178 (5) | 0.0212 (6) | 0.0125 (5) | 0.0049 (5) | 0.0051 (4) | −0.0003 (5) |
O2 | 0.0432 (10) | 0.0242 (8) | 0.0200 (8) | 0.0074 (7) | −0.0048 (7) | −0.0029 (6) |
O2B | 0.0193 (8) | 0.0277 (9) | 0.0151 (8) | 0.0027 (7) | 0.0079 (6) | 0.0033 (7) |
O3 | 0.0151 (7) | 0.0379 (10) | 0.0363 (10) | 0.0050 (7) | 0.0096 (7) | 0.0192 (8) |
O3B | 0.018 (4) | 0.024 (5) | 0.038 (6) | −0.002 (4) | 0.019 (4) | 0.001 (4) |
O4 | 0.0495 (11) | 0.0335 (10) | 0.0188 (8) | 0.0011 (8) | 0.0122 (7) | −0.0041 (7) |
O4B | 0.020 (6) | 0.032 (8) | 0.014 (6) | 0.014 (5) | 0.008 (5) | 0.005 (5) |
Pd1 | 0.01173 (5) | 0.01425 (6) | 0.01174 (6) | 0.00192 (5) | 0.00432 (4) | −0.00027 (4) |
Pd2 | 0.01268 (6) | 0.02854 (7) | 0.01189 (6) | 0.00021 (5) | 0.00602 (4) | 0.00231 (5) |
Cl1 | 0.02027 (19) | 0.0316 (2) | 0.0220 (2) | 0.01215 (18) | 0.01026 (16) | 0.00532 (18) |
Cl2 | 0.01481 (18) | 0.0442 (3) | 0.0303 (2) | 0.00095 (19) | 0.01044 (17) | 0.0005 (2) |
Cl3 | 0.0303 (2) | 0.0669 (4) | 0.0157 (2) | −0.0060 (3) | 0.01236 (19) | −0.0033 (2) |
C1—N1 | 1.496 (2) | C41—H41 | 0.9500 |
C1—C2 | 1.518 (2) | C42—C43 | 1.398 (3) |
C1—H1A | 0.9900 | C42—C46B | 1.46 (3) |
C1—H1B | 0.9900 | C42—C46 | 1.562 (10) |
C2—N2 | 1.503 (2) | C43—C44 | 1.395 (3) |
C2—H2A | 0.9900 | C43—H43 | 0.9500 |
C2—H2B | 0.9900 | C44—C45 | 1.410 (3) |
C3—N1 | 1.488 (2) | C44—C50 | 1.538 (3) |
C3—H3A | 0.9800 | C45—O4 | 1.382 (2) |
C3—H3B | 0.9800 | C45—H45 | 0.9500 |
C3—H3C | 0.9800 | C46—C47 | 1.518 (7) |
C4—N2 | 1.498 (2) | C46—C48 | 1.530 (7) |
C4—H4A | 0.9800 | C46—C49 | 1.533 (7) |
C4—H4B | 0.9800 | C47—H47A | 0.9800 |
C4—H4C | 0.9800 | C47—H47B | 0.9800 |
C5—C6 | 1.505 (2) | C47—H47C | 0.9800 |
C5—N1 | 1.509 (2) | C48—H48A | 0.9800 |
C5—H5A | 0.9900 | C48—H48B | 0.9800 |
C5—H5B | 0.9900 | C48—H48C | 0.9800 |
C6—C7 | 1.393 (2) | C49—H49A | 0.9800 |
C6—C11 | 1.417 (2) | C49—H49B | 0.9800 |
C7—C8 | 1.399 (3) | C49—H49C | 0.9800 |
C7—H7 | 0.9500 | C46B—C47B | 1.519 (16) |
C8—C9 | 1.396 (3) | C46B—C49B | 1.531 (16) |
C8—C12 | 1.534 (3) | C46B—C48B | 1.534 (15) |
C9—C10 | 1.399 (2) | C47B—H47D | 0.9800 |
C9—H9 | 0.9500 | C47B—H47E | 0.9800 |
C10—C11 | 1.419 (2) | C47B—H47F | 0.9800 |
C10—C16 | 1.542 (2) | C48B—H48D | 0.9800 |
C11—O1 | 1.346 (2) | C48B—H48E | 0.9800 |
C12—C14 | 1.526 (3) | C48B—H48F | 0.9800 |
C12—C15 | 1.531 (3) | C49B—H49D | 0.9800 |
C12—C13 | 1.538 (3) | C49B—H49E | 0.9800 |
C13—H13A | 0.9800 | C49B—H49F | 0.9800 |
C13—H13B | 0.9800 | C50—C51 | 1.535 (3) |
C13—H13C | 0.9800 | C50—C52 | 1.538 (3) |
C14—H14A | 0.9800 | C50—C53 | 1.540 (3) |
C14—H14B | 0.9800 | C51—H51A | 0.9800 |
C14—H14C | 0.9800 | C51—H51B | 0.9800 |
C15—H15A | 0.9800 | C51—H51C | 0.9800 |
C15—H15B | 0.9800 | C52—H52A | 0.9800 |
C15—H15C | 0.9800 | C52—H52B | 0.9800 |
C16—C19 | 1.535 (3) | C52—H52C | 0.9800 |
C16—C18 | 1.539 (3) | C53—H53A | 0.9800 |
C16—C17 | 1.542 (3) | C53—H53B | 0.9800 |
C17—H17A | 0.9800 | C53—H53C | 0.9800 |
C17—H17B | 0.9800 | C54—C55 | 1.507 (2) |
C17—H17C | 0.9800 | C54—N4 | 1.516 (2) |
C18—H18A | 0.9800 | C54—H54A | 0.9900 |
C18—H18B | 0.9800 | C54—H54B | 0.9900 |
C18—H18C | 0.9800 | C55—C56 | 1.394 (2) |
C19—H19A | 0.9800 | C55—C60 | 1.402 (2) |
C19—H19B | 0.9800 | C56—O3B | 1.377 (9) |
C19—H19C | 0.9800 | C56—C57 | 1.394 (3) |
C20—C21 | 1.509 (3) | C56—H56 | 0.9500 |
C20—N2 | 1.511 (2) | C57—C58 | 1.396 (3) |
C20—H20A | 0.9900 | C57—C61 | 1.536 (3) |
C20—H20B | 0.9900 | C58—C59 | 1.392 (3) |
C21—C22 | 1.396 (3) | C58—H58 | 0.9500 |
C21—C26 | 1.404 (2) | C59—C60 | 1.408 (3) |
C22—O2B | 1.350 (10) | C59—C65 | 1.535 (3) |
C22—C23 | 1.392 (3) | C60—O3 | 1.369 (2) |
C22—H22 | 0.9500 | C60—H60 | 0.9500 |
C23—C24 | 1.397 (3) | C61—C62 | 1.531 (3) |
C23—C27 | 1.537 (3) | C61—C64 | 1.542 (3) |
C24—C25 | 1.396 (3) | C61—C63 | 1.542 (3) |
C24—H24 | 0.9500 | C62—H62A | 0.9800 |
C25—C26 | 1.406 (3) | C62—H62B | 0.9800 |
C25—C31 | 1.543 (3) | C62—H62C | 0.9800 |
C26—O2 | 1.383 (2) | C63—H63A | 0.9800 |
C26—H26 | 0.9500 | C63—H63B | 0.9800 |
C27—C28 | 1.532 (3) | C63—H63C | 0.9800 |
C27—C30 | 1.533 (3) | C64—H64A | 0.9800 |
C27—C29 | 1.539 (3) | C64—H64B | 0.9800 |
C28—H28A | 0.9800 | C64—H64C | 0.9800 |
C28—H28B | 0.9800 | C65—C67 | 1.536 (3) |
C28—H28C | 0.9800 | C65—C66 | 1.540 (4) |
C29—H29A | 0.9800 | C65—C68 | 1.545 (3) |
C29—H29B | 0.9800 | C66—H66A | 0.9800 |
C29—H29C | 0.9800 | C66—H66B | 0.9800 |
C30—H30A | 0.9800 | C66—H66C | 0.9800 |
C30—H30B | 0.9800 | C67—H67A | 0.9800 |
C30—H30C | 0.9800 | C67—H67B | 0.9800 |
C31—C33 | 1.532 (3) | C67—H67C | 0.9800 |
C31—C34 | 1.535 (3) | C68—H68A | 0.9800 |
C31—C32 | 1.537 (3) | C68—H68B | 0.9800 |
C32—H32A | 0.9800 | C68—H68C | 0.9800 |
C32—H32B | 0.9800 | O5—C69 | 1.403 (5) |
C32—H32C | 0.9800 | O5—H5 | 0.8400 |
C33—H33A | 0.9800 | C69—H69A | 0.9800 |
C33—H33B | 0.9800 | C69—H69B | 0.9800 |
C33—H33C | 0.9800 | C69—H69C | 0.9800 |
C34—H34A | 0.9800 | O5B—H5C | 0.84 (2) |
C34—H34B | 0.9800 | O5B—H5D | 0.86 (2) |
C34—H34C | 0.9800 | O6—C70 | 1.405 (5) |
C35—C36 | 1.503 (3) | O6—H6 | 0.8400 |
C35—N3 | 1.503 (2) | C70—H70A | 0.9800 |
C35—H35A | 0.9900 | C70—H70B | 0.9800 |
C35—H35B | 0.9900 | C70—H70C | 0.9800 |
C36—N4 | 1.498 (2) | O6B—C70B | 1.373 (18) |
C36—H36A | 0.9900 | O6B—H6B | 0.8400 |
C36—H36B | 0.9900 | C70B—H70D | 0.9800 |
C37—N3 | 1.490 (2) | C70B—H70E | 0.9800 |
C37—H37A | 0.9800 | C70B—H70F | 0.9800 |
C37—H37B | 0.9800 | N1—Pd1 | 2.0369 (14) |
C37—H37C | 0.9800 | N2—Pd1 | 2.0739 (14) |
C38—N4 | 1.496 (2) | N3—Pd2 | 2.0699 (15) |
C38—H38A | 0.9800 | N4—Pd2 | 2.0735 (14) |
C38—H38B | 0.9800 | O1—Pd1 | 2.0085 (12) |
C38—H38C | 0.9800 | O2—H2 | 0.8400 |
C39—C40 | 1.511 (3) | O2B—H2C | 0.8400 |
C39—N3 | 1.515 (2) | O3—H3 | 0.8400 |
C39—H39A | 0.9900 | O3B—H3D | 0.8400 |
C39—H39B | 0.9900 | O4—H4 | 0.8400 |
C40—C41 | 1.396 (3) | O4B—H4D | 0.8400 |
C40—C45 | 1.403 (3) | Pd1—Cl1 | 2.3186 (4) |
C41—C42 | 1.393 (3) | Pd2—Cl3 | 2.3102 (5) |
C41—O4B | 1.410 (9) | Pd2—Cl2 | 2.3216 (5) |
N1—C1—C2 | 109.06 (14) | C45—C44—C50 | 121.37 (18) |
N1—C1—H1A | 109.9 | O4—C45—C40 | 122.71 (19) |
C2—C1—H1A | 109.9 | O4—C45—C44 | 116.44 (18) |
N1—C1—H1B | 109.9 | C40—C45—C44 | 120.79 (18) |
C2—C1—H1B | 109.9 | C40—C45—H45 | 119.6 |
H1A—C1—H1B | 108.3 | C44—C45—H45 | 119.6 |
N2—C2—C1 | 108.93 (14) | C47—C46—C48 | 109.4 (6) |
N2—C2—H2A | 109.9 | C47—C46—C49 | 109.2 (6) |
C1—C2—H2A | 109.9 | C48—C46—C49 | 107.5 (5) |
N2—C2—H2B | 109.9 | C47—C46—C42 | 109.8 (6) |
C1—C2—H2B | 109.9 | C48—C46—C42 | 111.7 (5) |
H2A—C2—H2B | 108.3 | C49—C46—C42 | 109.2 (5) |
N1—C3—H3A | 109.5 | C46—C47—H47A | 109.5 |
N1—C3—H3B | 109.5 | C46—C47—H47B | 109.5 |
H3A—C3—H3B | 109.5 | H47A—C47—H47B | 109.5 |
N1—C3—H3C | 109.5 | C46—C47—H47C | 109.5 |
H3A—C3—H3C | 109.5 | H47A—C47—H47C | 109.5 |
H3B—C3—H3C | 109.5 | H47B—C47—H47C | 109.5 |
N2—C4—H4A | 109.5 | C46—C48—H48A | 109.5 |
N2—C4—H4B | 109.5 | C46—C48—H48B | 109.5 |
H4A—C4—H4B | 109.5 | H48A—C48—H48B | 109.5 |
N2—C4—H4C | 109.5 | C46—C48—H48C | 109.5 |
H4A—C4—H4C | 109.5 | H48A—C48—H48C | 109.5 |
H4B—C4—H4C | 109.5 | H48B—C48—H48C | 109.5 |
C6—C5—N1 | 111.11 (14) | C46—C49—H49A | 109.5 |
C6—C5—H5A | 109.4 | C46—C49—H49B | 109.5 |
N1—C5—H5A | 109.4 | H49A—C49—H49B | 109.5 |
C6—C5—H5B | 109.4 | C46—C49—H49C | 109.5 |
N1—C5—H5B | 109.4 | H49A—C49—H49C | 109.5 |
H5A—C5—H5B | 108.0 | H49B—C49—H49C | 109.5 |
C7—C6—C11 | 120.74 (16) | C42—C46B—C47B | 112.4 (14) |
C7—C6—C5 | 119.95 (15) | C42—C46B—C49B | 109.6 (13) |
C11—C6—C5 | 119.27 (15) | C47B—C46B—C49B | 109.3 (15) |
C6—C7—C8 | 121.32 (17) | C42—C46B—C48B | 111.8 (14) |
C6—C7—H7 | 119.3 | C47B—C46B—C48B | 104.6 (14) |
C8—C7—H7 | 119.3 | C49B—C46B—C48B | 109.1 (14) |
C9—C8—C7 | 117.04 (16) | C46B—C47B—H47D | 109.5 |
C9—C8—C12 | 122.84 (17) | C46B—C47B—H47E | 109.5 |
C7—C8—C12 | 120.11 (17) | H47D—C47B—H47E | 109.5 |
C8—C9—C10 | 124.11 (17) | C46B—C47B—H47F | 109.5 |
C8—C9—H9 | 117.9 | H47D—C47B—H47F | 109.5 |
C10—C9—H9 | 117.9 | H47E—C47B—H47F | 109.5 |
C9—C10—C11 | 117.78 (16) | C46B—C48B—H48D | 109.5 |
C9—C10—C16 | 120.90 (16) | C46B—C48B—H48E | 109.5 |
C11—C10—C16 | 121.31 (15) | H48D—C48B—H48E | 109.5 |
O1—C11—C6 | 120.19 (15) | C46B—C48B—H48F | 109.5 |
O1—C11—C10 | 120.80 (15) | H48D—C48B—H48F | 109.5 |
C6—C11—C10 | 119.00 (16) | H48E—C48B—H48F | 109.5 |
C14—C12—C15 | 109.5 (2) | C46B—C49B—H49D | 109.5 |
C14—C12—C8 | 109.80 (18) | C46B—C49B—H49E | 109.5 |
C15—C12—C8 | 112.38 (18) | H49D—C49B—H49E | 109.5 |
C14—C12—C13 | 108.8 (2) | C46B—C49B—H49F | 109.5 |
C15—C12—C13 | 106.8 (2) | H49D—C49B—H49F | 109.5 |
C8—C12—C13 | 109.47 (18) | H49E—C49B—H49F | 109.5 |
C12—C13—H13A | 109.5 | C51—C50—C44 | 110.77 (17) |
C12—C13—H13B | 109.5 | C51—C50—C52 | 106.7 (2) |
H13A—C13—H13B | 109.5 | C44—C50—C52 | 111.90 (19) |
C12—C13—H13C | 109.5 | C51—C50—C53 | 110.3 (2) |
H13A—C13—H13C | 109.5 | C44—C50—C53 | 109.49 (18) |
H13B—C13—H13C | 109.5 | C52—C50—C53 | 107.55 (19) |
C12—C14—H14A | 109.5 | C50—C51—H51A | 109.5 |
C12—C14—H14B | 109.5 | C50—C51—H51B | 109.5 |
H14A—C14—H14B | 109.5 | H51A—C51—H51B | 109.5 |
C12—C14—H14C | 109.5 | C50—C51—H51C | 109.5 |
H14A—C14—H14C | 109.5 | H51A—C51—H51C | 109.5 |
H14B—C14—H14C | 109.5 | H51B—C51—H51C | 109.5 |
C12—C15—H15A | 109.5 | C50—C52—H52A | 109.5 |
C12—C15—H15B | 109.5 | C50—C52—H52B | 109.5 |
H15A—C15—H15B | 109.5 | H52A—C52—H52B | 109.5 |
C12—C15—H15C | 109.5 | C50—C52—H52C | 109.5 |
H15A—C15—H15C | 109.5 | H52A—C52—H52C | 109.5 |
H15B—C15—H15C | 109.5 | H52B—C52—H52C | 109.5 |
C19—C16—C18 | 107.87 (15) | C50—C53—H53A | 109.5 |
C19—C16—C17 | 107.20 (16) | C50—C53—H53B | 109.5 |
C18—C16—C17 | 109.50 (16) | H53A—C53—H53B | 109.5 |
C19—C16—C10 | 112.13 (16) | C50—C53—H53C | 109.5 |
C18—C16—C10 | 110.82 (15) | H53A—C53—H53C | 109.5 |
C17—C16—C10 | 109.22 (14) | H53B—C53—H53C | 109.5 |
C16—C17—H17A | 109.5 | C55—C54—N4 | 113.32 (14) |
C16—C17—H17B | 109.5 | C55—C54—H54A | 108.9 |
H17A—C17—H17B | 109.5 | N4—C54—H54A | 108.9 |
C16—C17—H17C | 109.5 | C55—C54—H54B | 108.9 |
H17A—C17—H17C | 109.5 | N4—C54—H54B | 108.9 |
H17B—C17—H17C | 109.5 | H54A—C54—H54B | 107.7 |
C16—C18—H18A | 109.5 | C56—C55—C60 | 118.83 (17) |
C16—C18—H18B | 109.5 | C56—C55—C54 | 119.49 (16) |
H18A—C18—H18B | 109.5 | C60—C55—C54 | 121.60 (16) |
C16—C18—H18C | 109.5 | O3B—C56—C55 | 125.6 (4) |
H18A—C18—H18C | 109.5 | O3B—C56—C57 | 112.4 (4) |
H18B—C18—H18C | 109.5 | C55—C56—C57 | 121.86 (17) |
C16—C19—H19A | 109.5 | C55—C56—H56 | 119.1 |
C16—C19—H19B | 109.5 | C57—C56—H56 | 119.1 |
H19A—C19—H19B | 109.5 | C56—C57—C58 | 117.18 (17) |
C16—C19—H19C | 109.5 | C56—C57—C61 | 119.84 (17) |
H19A—C19—H19C | 109.5 | C58—C57—C61 | 122.97 (17) |
H19B—C19—H19C | 109.5 | C59—C58—C57 | 123.78 (18) |
C21—C20—N2 | 114.07 (14) | C59—C58—H58 | 118.1 |
C21—C20—H20A | 108.7 | C57—C58—H58 | 118.1 |
N2—C20—H20A | 108.7 | C58—C59—C60 | 116.87 (17) |
C21—C20—H20B | 108.7 | C58—C59—C65 | 121.44 (18) |
N2—C20—H20B | 108.7 | C60—C59—C65 | 121.68 (17) |
H20A—C20—H20B | 107.6 | O3—C60—C55 | 123.03 (17) |
C22—C21—C26 | 119.40 (17) | O3—C60—C59 | 115.54 (17) |
C22—C21—C20 | 119.85 (16) | C55—C60—C59 | 121.40 (17) |
C26—C21—C20 | 120.75 (16) | C55—C60—H60 | 119.3 |
O2B—C22—C23 | 109.9 (6) | C59—C60—H60 | 119.3 |
O2B—C22—C21 | 128.2 (6) | C62—C61—C57 | 112.43 (18) |
C23—C22—C21 | 121.46 (17) | C62—C61—C64 | 107.75 (17) |
C23—C22—H22 | 119.3 | C57—C61—C64 | 108.80 (16) |
C21—C22—H22 | 119.3 | C62—C61—C63 | 108.59 (17) |
C22—C23—C24 | 117.35 (17) | C57—C61—C63 | 109.50 (16) |
C22—C23—C27 | 120.83 (17) | C64—C61—C63 | 109.73 (18) |
C24—C23—C27 | 121.78 (18) | C61—C62—H62A | 109.5 |
C25—C24—C23 | 123.80 (18) | C61—C62—H62B | 109.5 |
C25—C24—H24 | 118.1 | H62A—C62—H62B | 109.5 |
C23—C24—H24 | 118.1 | C61—C62—H62C | 109.5 |
C24—C25—C26 | 116.97 (17) | H62A—C62—H62C | 109.5 |
C24—C25—C31 | 121.19 (18) | H62B—C62—H62C | 109.5 |
C26—C25—C31 | 121.79 (17) | C61—C63—H63A | 109.5 |
O2—C26—C21 | 119.66 (17) | C61—C63—H63B | 109.5 |
O2—C26—C25 | 119.30 (17) | H63A—C63—H63B | 109.5 |
C21—C26—C25 | 120.98 (17) | C61—C63—H63C | 109.5 |
C21—C26—H26 | 119.5 | H63A—C63—H63C | 109.5 |
C25—C26—H26 | 119.5 | H63B—C63—H63C | 109.5 |
C28—C27—C30 | 107.6 (2) | C61—C64—H64A | 109.5 |
C28—C27—C23 | 111.93 (18) | C61—C64—H64B | 109.5 |
C30—C27—C23 | 108.53 (17) | H64A—C64—H64B | 109.5 |
C28—C27—C29 | 110.0 (2) | C61—C64—H64C | 109.5 |
C30—C27—C29 | 108.28 (19) | H64A—C64—H64C | 109.5 |
C23—C27—C29 | 110.36 (18) | H64B—C64—H64C | 109.5 |
C27—C28—H28A | 109.5 | C59—C65—C67 | 109.51 (19) |
C27—C28—H28B | 109.5 | C59—C65—C66 | 110.16 (18) |
H28A—C28—H28B | 109.5 | C67—C65—C66 | 111.9 (2) |
C27—C28—H28C | 109.5 | C59—C65—C68 | 112.03 (19) |
H28A—C28—H28C | 109.5 | C67—C65—C68 | 106.3 (2) |
H28B—C28—H28C | 109.5 | C66—C65—C68 | 106.9 (2) |
C27—C29—H29A | 109.5 | C65—C66—H66A | 109.5 |
C27—C29—H29B | 109.5 | C65—C66—H66B | 109.5 |
H29A—C29—H29B | 109.5 | H66A—C66—H66B | 109.5 |
C27—C29—H29C | 109.5 | C65—C66—H66C | 109.5 |
H29A—C29—H29C | 109.5 | H66A—C66—H66C | 109.5 |
H29B—C29—H29C | 109.5 | H66B—C66—H66C | 109.5 |
C27—C30—H30A | 109.5 | C65—C67—H67A | 109.5 |
C27—C30—H30B | 109.5 | C65—C67—H67B | 109.5 |
H30A—C30—H30B | 109.5 | H67A—C67—H67B | 109.5 |
C27—C30—H30C | 109.5 | C65—C67—H67C | 109.5 |
H30A—C30—H30C | 109.5 | H67A—C67—H67C | 109.5 |
H30B—C30—H30C | 109.5 | H67B—C67—H67C | 109.5 |
C33—C31—C34 | 107.34 (18) | C65—C68—H68A | 109.5 |
C33—C31—C32 | 109.30 (18) | C65—C68—H68B | 109.5 |
C34—C31—C32 | 108.01 (17) | H68A—C68—H68B | 109.5 |
C33—C31—C25 | 111.72 (16) | C65—C68—H68C | 109.5 |
C34—C31—C25 | 112.10 (17) | H68A—C68—H68C | 109.5 |
C32—C31—C25 | 108.29 (16) | H68B—C68—H68C | 109.5 |
C31—C32—H32A | 109.5 | C69—O5—H5 | 109.5 |
C31—C32—H32B | 109.5 | O5—C69—H69A | 109.5 |
H32A—C32—H32B | 109.5 | O5—C69—H69B | 109.5 |
C31—C32—H32C | 109.5 | H69A—C69—H69B | 109.5 |
H32A—C32—H32C | 109.5 | O5—C69—H69C | 109.5 |
H32B—C32—H32C | 109.5 | H69A—C69—H69C | 109.5 |
C31—C33—H33A | 109.5 | H69B—C69—H69C | 109.5 |
C31—C33—H33B | 109.5 | H5C—O5B—H5D | 107 (3) |
H33A—C33—H33B | 109.5 | C70—O6—H6 | 109.5 |
C31—C33—H33C | 109.5 | O6—C70—H70A | 109.5 |
H33A—C33—H33C | 109.5 | O6—C70—H70B | 109.5 |
H33B—C33—H33C | 109.5 | H70A—C70—H70B | 109.5 |
C31—C34—H34A | 109.5 | O6—C70—H70C | 109.5 |
C31—C34—H34B | 109.5 | H70A—C70—H70C | 109.5 |
H34A—C34—H34B | 109.5 | H70B—C70—H70C | 109.5 |
C31—C34—H34C | 109.5 | C70B—O6B—H6B | 109.5 |
H34A—C34—H34C | 109.5 | O6B—C70B—H70D | 109.5 |
H34B—C34—H34C | 109.5 | O6B—C70B—H70E | 109.5 |
C36—C35—N3 | 109.55 (15) | H70D—C70B—H70E | 109.5 |
C36—C35—H35A | 109.8 | O6B—C70B—H70F | 109.5 |
N3—C35—H35A | 109.8 | H70D—C70B—H70F | 109.5 |
C36—C35—H35B | 109.8 | H70E—C70B—H70F | 109.5 |
N3—C35—H35B | 109.8 | C3—N1—C1 | 110.84 (14) |
H35A—C35—H35B | 108.2 | C3—N1—C5 | 110.38 (13) |
N4—C36—C35 | 110.01 (14) | C1—N1—C5 | 109.91 (13) |
N4—C36—H36A | 109.7 | C3—N1—Pd1 | 111.59 (10) |
C35—C36—H36A | 109.7 | C1—N1—Pd1 | 104.61 (10) |
N4—C36—H36B | 109.7 | C5—N1—Pd1 | 109.36 (10) |
C35—C36—H36B | 109.7 | C4—N2—C2 | 108.85 (14) |
H36A—C36—H36B | 108.2 | C4—N2—C20 | 106.92 (14) |
N3—C37—H37A | 109.5 | C2—N2—C20 | 111.12 (13) |
N3—C37—H37B | 109.5 | C4—N2—Pd1 | 105.61 (11) |
H37A—C37—H37B | 109.5 | C2—N2—Pd1 | 107.53 (10) |
N3—C37—H37C | 109.5 | C20—N2—Pd1 | 116.48 (10) |
H37A—C37—H37C | 109.5 | C37—N3—C35 | 110.58 (15) |
H37B—C37—H37C | 109.5 | C37—N3—C39 | 107.41 (14) |
N4—C38—H38A | 109.5 | C35—N3—C39 | 110.12 (14) |
N4—C38—H38B | 109.5 | C37—N3—Pd2 | 106.95 (11) |
H38A—C38—H38B | 109.5 | C35—N3—Pd2 | 106.93 (11) |
N4—C38—H38C | 109.5 | C39—N3—Pd2 | 114.81 (11) |
H38A—C38—H38C | 109.5 | C38—N4—C36 | 110.64 (15) |
H38B—C38—H38C | 109.5 | C38—N4—C54 | 107.70 (14) |
C40—C39—N3 | 112.59 (14) | C36—N4—C54 | 110.40 (14) |
C40—C39—H39A | 109.1 | C38—N4—Pd2 | 107.06 (11) |
N3—C39—H39A | 109.1 | C36—N4—Pd2 | 106.65 (11) |
C40—C39—H39B | 109.1 | C54—N4—Pd2 | 114.35 (11) |
N3—C39—H39B | 109.1 | C11—O1—Pd1 | 121.65 (10) |
H39A—C39—H39B | 107.8 | C26—O2—H2 | 109.5 |
C41—C40—C45 | 119.42 (18) | C22—O2B—H2C | 109.5 |
C41—C40—C39 | 119.16 (17) | C60—O3—H3 | 109.5 |
C45—C40—C39 | 121.31 (18) | C56—O3B—H3D | 109.5 |
C42—C41—C40 | 121.61 (18) | C45—O4—H4 | 109.5 |
C42—C41—O4B | 110.6 (5) | C41—O4B—H4D | 109.5 |
C40—C41—O4B | 127.5 (5) | O1—Pd1—N1 | 93.18 (5) |
C42—C41—H41 | 119.2 | O1—Pd1—N2 | 170.29 (5) |
C40—C41—H41 | 119.2 | N1—Pd1—N2 | 85.84 (6) |
C41—C42—C43 | 117.19 (18) | O1—Pd1—Cl1 | 88.04 (4) |
C41—C42—C46B | 122.6 (7) | N1—Pd1—Cl1 | 178.20 (4) |
C43—C42—C46B | 120.2 (7) | N2—Pd1—Cl1 | 93.17 (4) |
C41—C42—C46 | 120.0 (3) | N3—Pd2—N4 | 85.44 (6) |
C43—C42—C46 | 122.7 (3) | N3—Pd2—Cl3 | 175.32 (5) |
C44—C43—C42 | 123.79 (18) | N4—Pd2—Cl3 | 91.99 (4) |
C44—C43—H43 | 118.1 | N3—Pd2—Cl2 | 93.02 (4) |
C42—C43—H43 | 118.1 | N4—Pd2—Cl2 | 175.77 (4) |
C43—C44—C45 | 117.08 (18) | Cl3—Pd2—Cl2 | 89.801 (19) |
C43—C44—C50 | 121.56 (19) | ||
N1—C1—C2—N2 | 53.29 (19) | C41—C40—C45—C44 | 4.1 (3) |
N1—C5—C6—C7 | 118.98 (18) | C39—C40—C45—C44 | −172.13 (17) |
N1—C5—C6—C11 | −58.7 (2) | C43—C44—C45—O4 | −179.38 (17) |
C11—C6—C7—C8 | 0.1 (3) | C50—C44—C45—O4 | 0.9 (3) |
C5—C6—C7—C8 | −177.60 (17) | C43—C44—C45—C40 | −2.1 (3) |
C6—C7—C8—C9 | 0.1 (3) | C50—C44—C45—C40 | 178.18 (17) |
C6—C7—C8—C12 | 178.80 (18) | C41—C42—C46—C47 | −50.7 (6) |
C7—C8—C9—C10 | 0.3 (3) | C43—C42—C46—C47 | 132.9 (5) |
C12—C8—C9—C10 | −178.30 (18) | C41—C42—C46—C48 | −172.2 (3) |
C8—C9—C10—C11 | −0.9 (3) | C43—C42—C46—C48 | 11.3 (6) |
C8—C9—C10—C16 | 177.85 (17) | C41—C42—C46—C49 | 69.0 (5) |
C7—C6—C11—O1 | 178.73 (16) | C43—C42—C46—C49 | −107.5 (4) |
C5—C6—C11—O1 | −3.6 (2) | C41—C42—C46B—C47B | −14.7 (15) |
C7—C6—C11—C10 | −0.7 (3) | C43—C42—C46B—C47B | 165.7 (10) |
C5—C6—C11—C10 | 176.96 (16) | C41—C42—C46B—C49B | 107.0 (11) |
C9—C10—C11—O1 | −178.33 (16) | C43—C42—C46B—C49B | −72.6 (12) |
C16—C10—C11—O1 | 2.9 (3) | C41—C42—C46B—C48B | −131.9 (10) |
C9—C10—C11—C6 | 1.1 (2) | C43—C42—C46B—C48B | 48.5 (13) |
C16—C10—C11—C6 | −177.67 (16) | C43—C44—C50—C51 | 121.2 (2) |
C9—C8—C12—C14 | −118.9 (2) | C45—C44—C50—C51 | −59.1 (3) |
C7—C8—C12—C14 | 62.5 (3) | C43—C44—C50—C52 | 2.3 (3) |
C9—C8—C12—C15 | 3.3 (3) | C45—C44—C50—C52 | −178.01 (18) |
C7—C8—C12—C15 | −175.29 (19) | C43—C44—C50—C53 | −116.9 (2) |
C9—C8—C12—C13 | 121.8 (2) | C45—C44—C50—C53 | 62.8 (3) |
C7—C8—C12—C13 | −56.8 (3) | N4—C54—C55—C56 | −76.3 (2) |
C9—C10—C16—C19 | −0.2 (2) | N4—C54—C55—C60 | 100.40 (19) |
C11—C10—C16—C19 | 178.51 (17) | C60—C55—C56—O3B | 172.4 (6) |
C9—C10—C16—C18 | 120.36 (19) | C54—C55—C56—O3B | −10.7 (6) |
C11—C10—C16—C18 | −60.9 (2) | C60—C55—C56—C57 | −3.1 (3) |
C9—C10—C16—C17 | −118.92 (18) | C54—C55—C56—C57 | 173.71 (17) |
C11—C10—C16—C17 | 59.8 (2) | O3B—C56—C57—C58 | −174.5 (5) |
N2—C20—C21—C22 | 78.3 (2) | C55—C56—C57—C58 | 1.6 (3) |
N2—C20—C21—C26 | −102.40 (19) | O3B—C56—C57—C61 | 6.2 (5) |
C26—C21—C22—O2B | −170.5 (8) | C55—C56—C57—C61 | −177.76 (17) |
C20—C21—C22—O2B | 8.8 (9) | C56—C57—C58—C59 | 1.0 (3) |
C26—C21—C22—C23 | 1.5 (3) | C61—C57—C58—C59 | −179.65 (18) |
C20—C21—C22—C23 | −179.18 (16) | C57—C58—C59—C60 | −1.9 (3) |
O2B—C22—C23—C24 | 173.6 (7) | C57—C58—C59—C65 | 178.98 (19) |
C21—C22—C23—C24 | 0.3 (3) | C56—C55—C60—O3 | −179.92 (18) |
O2B—C22—C23—C27 | −8.7 (7) | C54—C55—C60—O3 | 3.3 (3) |
C21—C22—C23—C27 | 177.93 (17) | C56—C55—C60—C59 | 2.1 (3) |
C22—C23—C24—C25 | −0.9 (3) | C54—C55—C60—C59 | −174.65 (17) |
C27—C23—C24—C25 | −178.51 (17) | C58—C59—C60—O3 | −177.80 (17) |
C23—C24—C25—C26 | −0.3 (3) | C65—C59—C60—O3 | 1.3 (3) |
C23—C24—C25—C31 | 177.28 (17) | C58—C59—C60—C55 | 0.3 (3) |
C22—C21—C26—O2 | −179.78 (17) | C65—C59—C60—C55 | 179.41 (18) |
C20—C21—C26—O2 | 0.9 (3) | C56—C57—C61—C62 | −177.19 (17) |
C22—C21—C26—C25 | −2.7 (3) | C58—C57—C61—C62 | 3.5 (3) |
C20—C21—C26—C25 | 177.94 (16) | C56—C57—C61—C64 | 63.5 (2) |
C24—C25—C26—O2 | 179.19 (17) | C58—C57—C61—C64 | −115.8 (2) |
C31—C25—C26—O2 | 1.6 (3) | C56—C57—C61—C63 | −56.4 (2) |
C24—C25—C26—C21 | 2.1 (3) | C58—C57—C61—C63 | 124.3 (2) |
C31—C25—C26—C21 | −175.45 (16) | C58—C59—C65—C67 | −118.5 (2) |
C22—C23—C27—C28 | 164.4 (2) | C60—C59—C65—C67 | 62.4 (3) |
C24—C23—C27—C28 | −18.1 (3) | C58—C59—C65—C66 | 118.0 (2) |
C22—C23—C27—C30 | −77.0 (2) | C60—C59—C65—C66 | −61.0 (3) |
C24—C23—C27—C30 | 100.6 (2) | C58—C59—C65—C68 | −0.8 (3) |
C22—C23—C27—C29 | 41.6 (3) | C60—C59—C65—C68 | −179.8 (2) |
C24—C23—C27—C29 | −140.9 (2) | C2—C1—N1—C3 | 72.40 (18) |
C24—C25—C31—C33 | 122.7 (2) | C2—C1—N1—C5 | −165.31 (14) |
C26—C25—C31—C33 | −59.8 (2) | C2—C1—N1—Pd1 | −48.00 (16) |
C24—C25—C31—C34 | 2.2 (3) | C6—C5—N1—C3 | −54.56 (18) |
C26—C25—C31—C34 | 179.64 (18) | C6—C5—N1—C1 | −177.13 (14) |
C24—C25—C31—C32 | −116.9 (2) | C6—C5—N1—Pd1 | 68.57 (15) |
C26—C25—C31—C32 | 60.6 (2) | C1—C2—N2—C4 | 83.83 (17) |
N3—C35—C36—N4 | −52.50 (19) | C1—C2—N2—C20 | −158.69 (14) |
N3—C39—C40—C41 | −78.3 (2) | C1—C2—N2—Pd1 | −30.14 (16) |
N3—C39—C40—C45 | 98.0 (2) | C21—C20—N2—C4 | 175.21 (15) |
C45—C40—C41—C42 | −3.4 (3) | C21—C20—N2—C2 | 56.55 (19) |
C39—C40—C41—C42 | 172.91 (17) | C21—C20—N2—Pd1 | −67.03 (17) |
C45—C40—C41—O4B | 169.6 (7) | C36—C35—N3—C37 | −77.92 (18) |
C39—C40—C41—O4B | −14.1 (8) | C36—C35—N3—C39 | 163.52 (15) |
C40—C41—C42—C43 | 0.7 (3) | C36—C35—N3—Pd2 | 38.17 (16) |
O4B—C41—C42—C43 | −173.4 (6) | C40—C39—N3—C37 | −173.44 (16) |
C40—C41—C42—C46B | −178.9 (7) | C40—C39—N3—C35 | −53.0 (2) |
O4B—C41—C42—C46B | 7.0 (10) | C40—C39—N3—Pd2 | 67.78 (18) |
C40—C41—C42—C46 | −176.0 (3) | C35—C36—N4—C38 | −77.38 (18) |
C41—C42—C43—C44 | 1.4 (3) | C35—C36—N4—C54 | 163.50 (15) |
C46B—C42—C43—C44 | −178.9 (7) | C35—C36—N4—Pd2 | 38.72 (17) |
C46—C42—C43—C44 | 178.0 (3) | C55—C54—N4—C38 | −168.30 (15) |
C42—C43—C44—C45 | −0.8 (3) | C55—C54—N4—C36 | −47.40 (19) |
C42—C43—C44—C50 | 178.99 (17) | C55—C54—N4—Pd2 | 72.86 (16) |
C41—C40—C45—O4 | −178.74 (18) | C6—C11—O1—Pd1 | 44.6 (2) |
C39—C40—C45—O4 | 5.0 (3) | C10—C11—O1—Pd1 | −135.99 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O1 | 0.84 | 1.95 | 2.787 (3) | 171 |
C69—H69A···Cl1 | 0.98 | 2.90 | 3.642 (4) | 134 |
C69—H69C···O3 | 0.98 | 2.57 | 3.267 (4) | 128 |
O5B—H5C···O1 | 0.84 (2) | 1.95 (3) | 2.772 (6) | 168 (12) |
O6—H6···Cl2 | 0.84 | 2.90 | 3.592 (2) | 141 |
O6—H6···Cl3 | 0.84 | 2.41 | 3.129 (2) | 144 |
O6B—H6B···Cl2 | 0.84 | 2.45 | 3.242 (13) | 157 |
O2—H2···O5i | 0.84 | 1.88 | 2.715 (3) | 170 |
O2B—H2C···Cl1 | 0.84 | 2.06 | 2.858 (13) | 157 |
O3—H3···Cl1 | 0.84 | 2.46 | 3.1764 (17) | 144 |
O3B—H3D···Cl3 | 0.84 | 2.12 | 2.886 (10) | 152 |
O4—H4···O6ii | 0.84 | 1.95 | 2.750 (3) | 160 |
O4B—H4D···Cl2 | 0.84 | 2.05 | 2.726 (12) | 137 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2. |
Complex | Reference | N—Pd—N |
[(κ2-N,N)PdCl2] | This work | 85.44 |
[(κ3-N,N,O)PdCl] | This work | 85.84 |
[(κ2-N,N)PdCl2] | Graziano et al. (2019) | 82.8 |
[(κ2-N,N)PdCl2] | Graziano et al. (2019) | 85.58 |
[(κ3-N,N,O)PdCl] | Graziano et al. (2019) | 82.82 |
[(κ3-N,N,O)PdCl] | Graziano et al. (2019) | 86.86 |
[(κ3-N,N,O)PdCl] | Graziano et al. (2019) | 82.9 |
[(κ3-N,N,O)PdCl] | Graziano et al. (2019) | 83.0 |
[(κ2-N,N,)PdCl2] | Ding et al. (2011) | 84.07 |
Funding information
Acknowledgment is made to the donors of the American Chemical Society Petroleum Research Fund for support (or partial support) of this research (grant No. 56549-UR3). This material is based upon work supported by the National Science Foundation through the Major Research Instrumentation Program under grant No. CHE 1625543 (funding for the single-crystal X-ray diffractometer).
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