research communications
Tris(N-{bis[methyl(phenyl)amino]phosphoryl}benzenesulfonamidato-κ2O,O′)(1,10-phenanthroline-κ2N,N′)lanthanum(III)
aNational Taras Shevchenko University of Kyiv, Department of Chemistry, 12 Lva Tolstogo str., 01033 Kyiv, Ukraine, and bSTC "Institute for Single Crystals", 60 Nauki ave., Kharkiv 61072, Ukraine
*Correspondence e-mail: AngelinaPritula@gmail.com
The 20H21N3O3PS)3(C12H8N2)] is created by one LaIII ion, three deprotonated N-{bis[methyl(phenyl)amino]phosphoryl}benzenesulfonamidate (L−) ligands and one 1,10-phenanthroline (Phen) molecule. Each LaIII ion is eight-coordinated (6O+2N) by three phosphoryl O atoms, three sulfonyl O atoms of three L− ligands and two N atoms of the chelating Phen ligand, leading to the formation of six- and five-membered metallacycles, respectively. The lanthanum has a bicapped trigonal–prismatic geometry. `Sandwich-like' intramolecular π–π stacking interactions are observed between the 1,10-phenanthroline ligand and two benzene rings of two different L− ligands. The phenyl rings of L− that are not involved in the stacking interactions show minor positional disorder. Molecules form layers parallel to the (010) plane due to weak C—H⋯O intermolecular hydrogen bonds. Unidentified highly disordered solvate molecules that occupy ca 400 Å3 large voids have been omitted from the model.
of [La(CKeywords: crystal structure; phosphorylated sulfonylamide; sulfonylamidophosphate; π–π stacking; eight-coordinated lanthanide complex.
CCDC reference: 1556367
1. Chemical context
β-Diketone derivatives have been the topic of investigations in many different branches of the chemical science, such as organic, coordination, bio- and theoretical chemistry. Of special interest have been carbacylamidophosphates (CAPh), containing the functional fragment C(O)NHP(O), because of their properties as extractants (Morgalyuk et al., 2005; Safiulina et al., 2015), urease inhibitors (Jaroslav & Swerdloff, 1985), enzyme inhibitors (Grimes et al., 2008; Adams et al., 2002), their antibacterial properties (Oroujzadeh et al., 2017) and anticancer activity (Kovalchyk et al., 1991; Amirkhanov et al., 1995). The presence of the phosphoryl group gives them a high affinity towards highly charged metal ions, and these types of compounds are used in the coordination chemistry of lanthanides and actinides (Litsis et al., 2010, 2017; Kariaka et al., 2013). Many efforts have been devoted to the synthesis of another type of structural analogs of β-diketones – sulfonylamidophosphates (SAPh) with the structural fragment S(O)2NHP(O). These types of compounds were first synthesized by Kirsanov (Kirsanov & Shevchenko, 1954) and some have since been used as bactericidal agents in medicine and toxicology (Xu & Angell, 2000), while others have found use as pesticides (Kishino & Saito, 1979). In addition, these compounds are potentially bidentate O,O-donor chelating ligands for metal ions, similar to other deprotonated phosphorylic ligand derivatives (Znovjyak et al., 2015; Amirkhanov et al., 2014; Litsis et al., 2016; Shatrava et al., 2016a). For details of the coordination chemistry of phosphorylic ligands in molecular form, see Gholivand et al. (2012, 2014), Yizhak et al. (2013) and Shatrava et al. (2016b).
Recently, we reported the preparation and study of the coordination properties of several representatives of sulfonylamidophosphates: methyl(phenylsulfonyl)amidophosphate [PhSO2NHP(O)(OMe)2] (Moroz et al., 2007) and particularly the photophysical properties of a series of NIR-emitting lanthanide complexes (Kulesza et al., 2010). It was shown that the solid-state for the ytterbium complex is one of the longest of all known YbIII complexes with organic ligands. It is expected that depending on the nature of substituents attached to the phosphorus and sulfur atoms, these organic compounds and their complexes might demonstrate unique specific physicochemical properties. Optical studies of the etheric type SAPh ligands dimethyl(4-methylphenylsulfonyl)amidophosphate [(Me)PhSO2NHP(O)(OMe)2] and dimethyl 2-naphthylsulfonylamidophosphate [(C10H7)SO2NHP(O)(OMe)2] indicate that the ligand first excited plays a dominant role in intramolecular processes in these Ln complexes (Kasprzycka et al., 2016).
Knowledge of the N-(methyl(phenylamino)phosphoryl)benzenesulfonamide (HL) [PhSO2NHP(O)(N(Me)Ph)2] with the general formula La(L)3Phen.
is an essential part of understanding the luminescent properties of these types of lanthanide complexes. In this paper we would therefore like to report the molecular and of a lanthanum coordination compound based on the amidic type SAPh ligand2. Structural commentary
The title compound La(L)3Phen crystallizes with one molecule in the (Fig. 1). The coordination environment of the La atom consists of two nitrogen atoms of 1,10-phenanthroline and six oxygen atoms from the three acido-SAPh ligands.
The La—O(S) bond lengths [2.516 (2)–2.541 (2) Å] are all longer than those of their La—O(P) counterparts [2.424 (2)–2.463 (2) Å], with mean values of 2.435 and 2.456 Å, respectively. The mean average of all La—O bond lengths is 2.476 Å. The La—N distances are with 2.699 (3) and 2.700 (3) Å (mean value 2.693 Å) shorter than those previously obtained for a 1,10-phenanthrolinate lanthanum (III) complex with hexafluoroacetylacetonate (2.747–2.782 Å; Rogachev et al., 2005) and longer than La—N bonds in a carbacylamidophosphate ligand complex (2.601–2.635 Å; Litsis et al., 2015; Sokolnicki et al., 1999).
The SAPh ligands coordinate to the lanthanide atom in the acido form in a bidentate manner with formation of six-membered metallocycles with partial delocalization of π-electron density. The values of the S—O and P—O bonds are at 1.462 (3)–1.474 (2) Å and 1.491 (2)–1.494 (2) Å in their expected ranges. The mean values are 1.468 and 1.492 Å, respectively. The corresponding bond lengths in the related neutral ligands are around 1.42 Å (Moroz et al., 2012) and 1.48 Å (Znovjyak et al., 2009). The S—O bonds of the SAPh ligands of the non-coordinating oxygen atom are systematically shorter [1.432 (3)–1.437 (3) Å], indicating more S=O double-bond character than for the coordinating O atoms.
The six-membered metallocyclic rings with the chelate (O)PNS(O) fragments are all non-planar. The La1–O1–P1–N1–S1–O1 (A) and La1–O3–P3–N3–S3–O9 (B) rings both adopt twist-boat conformations (puckering parameters are: S = 0.61, ψ = 22.11°, θ = 79.68° for A and S = 0.75, ψ = 24.44°, θ = 87.28° for B, respectively (Zefirov et al., 1990)). The deviations of the N1 and O1 atoms from the mean plane through the remaining atoms of A (r.m.s.deviation = 0.06 Å) are 0.78 and 0.41 Å, respectively. The deviations of the La1 and O3 atoms from the mean plane through the remaining atoms of B (r.m.s.deviation = 0.06 Å) are 0.9 and 0.88 Å, respectively. The La1–O2–P2–N2–S2–O7 (C) ring adopts a flattened half-chair conformation (puckering parameters are: S = 0.71, ψ = 16.51°, θ = 20.43°). The deviation of the La1 atom from the mean plane carried through the remaining atoms of ring C (r.m.s.deviation 0.02 Å) is 0.36 Å.
The δ-criterions were used to characterize the lanthanum ion eight-apical (Porai-Koshits & Aslanov, 1972). The set of the angles δ between pairs of the faces intersecting along the type b edges (shown in Fig. 2) allows us to assign a distorted bicapped trigonal–prismatic environment (δ1 = 9.48°, δ2 = 18.48°, δ3 = 43.57°, δ4 = 44.89°, φ1 = 12.47°, φ2 = 16.05°) similar to that of the Tb(Pip)3(Phen) mixed-ligand complex with 2,2,2-trichloro-N-(dipiperidin-1-yl-phosphoryl)acetamide, HPip (Litsis et al., 2015).
Intramolecular `sandwich-like' π–π-stacking interactions are observed between the 1.10-phenanthroline fragments and two phenyl rings of the two SAPh ligands of the title molecule. The central ring C66(π)⋯C69(π) of the 1,10-phenanthroline molecule interacts with the C41(π)⋯C46(π) phenyl ring at the sulfonyl group from another ligand [interplanar angle 2.8 (1)°, intercentroid distance 3.646 (2) Å, interplanar separation 3.38–3.41 Å, plane shift 1.29–1.36 Å], and with the C8(π)⋯C13(π) ring at the phosphoryl group from the other ligand [interplanar angle 2.5 (2)°, intercentroid distance 3.879 (3) Å, interplanar separation 3.49–3.52 Å, plane shift 1.62–1.69 Å]. A similar intramolecular organization was described previously for related compounds (Beloso et al., 2003).
3. Supramolecular features
In the crystal phase, the La(L)3Phen molecules are linked by weak C—H⋯O hydrogen bonds (Table 1), forming double layers parallel to the (010) plane (Fig. 3). There are solvent-accessible voids with a total volume of 380 Å3. The content of the voids is not resolved in difference-density maps, with the largest residual electron density peak being only 0.66 electrons per Å3. A SQUEEZE (Spek, 2015) analysis indicated an overall electron count matching approximately three molecules of the solvent (2-propanol) per but did not improve R values or other quality indicators (see Refinement section).
4. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.38, update February 2017; Groom et al., 2016) for SAPh ligand analogues with derivatives of the N-(bis(diamino)phosphoryl)sulfonamide fragments yielded five hits, with only one metal complex structure with a neodymium metal atom among them (Shatrava et al., 2010). In this molecule, the neodymium atom is also octacoordinated, with a highly symmetrical NdO8 polyhedron and no coordinating N atoms.
A search for phenanthrolinate REE complexes with other SAPh-type ligands returned one entry for tris(dimethyl (phenylsulfonyl)phosphoramidato-O,O′)-(1,10-phenanthroline-N,N′)-erbium(III) (SAPHICP; Gawryszewska et al., 2011).
A search for octacoordinated La complexes with an LaN2O6 environment yielded 20 hits, with average La—O and La—N bond lengths of 2.476 and 2.693 Å, respectively. 11 complex structures with different lanthanoid metals (Ln) containing Ln–O–P–N–S–O metallocycles were found in the database, all with octacoordinated metal atoms. Most of those metallacyclic rings are non-planar with mean deviations of the O and N atoms of 0.329 and 0.434 Å, respectively.
5. Synthesis and crystallization
1H and 31P NMR spectra in DMSO-d6 solutions were recorded on a Varian 400 NMR spectrometer at room temperature. 1H chemical shifts were determined relative to the internal standard TMS whereas 31P chemical shifts were determined relative to 85% H3PO4 as an Infrared (FTIR) spectra were recorded on a Perkin–Elmer Spectrum BX spectrometer using KBr pellets. The resolution of the FTIR spectra is 1 cm−1.
Sulfonylamidophosphate ligand N-(methyl(phenylamino)phosphoryl)benzenesulfonamide (HL) was synthesized via a three-step procedure based on the Kirsanov reaction (Kirsanov & Shevchenko, 1954). 1H NMR (400 MHz, DMSO-d6, 293 K) δ 2.95 (d, J = 7.6, 6H, CH3), 7.05 (t, J = 5.6, 2H, γ-CHphenylamino), 7.14 (d, J = 6.4, 4H, α-CHphenylamino), 7.21 (t, J = 6.2, 4H, β-CHphenylamino), 7.56 (t, J = 6.2, 2H, β-CH), 7.65 (t, J = 6.2, 1H, γ-CH), 7.91 (d, J = 6.0, 2H, α-CH).
IR (KBr pellet, cm−1): 3062 [m, ν (C—Haliph)], 2948 [m, ν (C—Harom)], 2780 [m, ν(N—H)], 2705 [m, ν(C—Harom)], 2655 [w, ν(C—Harom)], 1594 [s, ν(S=N)], 1495 (s), 1446 (m), 1400 (m), 1330 [s, ν(S=O2)], 1279 (m), 1220 [ws, ν(P=O)], 1168 [s, ρ(CH3)], 1084 (m), 1069 (m), 1028 (m), 920 [ws, ν(P—N)], 887 (ws), 765 (s), 758 (s), 723 (m), 696 (s), 685 (s), 602 (m), 573 (m), 558 (m), 551 (m), 542 (m), 508 (s), 490 (m), 442 (w).
The sodium salt (NaL) was prepared by the reaction between equimolar amounts of sodium methanolate (0.069 g, 3 mmol of Na was dissolved in 20 ml of methanol) and HL (1.39 g, 3 mmol) in an methanol medium (20 ml). The mixture was heated with magnetic stirring at 337 K for 10 min. The resulting solution was evaporated and the fine crystalline powder was isolated (yield 83%) and washed with 2-propanol. Dry product NaL was used for the preparation of the complexes. 1H NMR (400 MHz, DMSO-d6, 290 K) δ 3.46 (s, 3H, CH3), 3.48 (s, 3H, CH3), 7.26 (t, J = 7.2, 2H, γ-CHphenylamino), 7.53 (t, J = 8, 4H, β-CHphenylamino), 7.6 (d, J = 8.4, 4H, α-CHphenylamino), 7.77 (m, 5H, CH). 31P NMR (400 MHz, DMSO-d6, 290 K) δ 54.01.
IR (KBr pellet, cm−1): 3068 [m, ν (C—Haliph)], 2944 [m, ν(C—Harom.)], 2704 [m, ν(C—Harom)], 2660 [w, ν(C—Harom)], 1581 [s, ν(S=N)], 1490 (s), 1410 [m, ν(C=C)], 1263 [s, ν(S=O2)], 1271 (m), 1173 [ws, ν(P=O)], 1165 [s, ρ(CH3)], 1080 (m), 1031 (m), 891 [ws, ν(P—N], 870 (ws), 761 (s), 747 (s), 720 (m), 695 (s), 680 (s), 573 (m), 551 (m), 540 (m), 503 (s), 485 (m), 432 (w).
Preparation of La(L)3Phen. NaL (0.728 g, 1.5 mmol) was dissolved in 7 ml of 2-propanol and was added to a solution of 1,10-phenanthroline monohydrate (0.0991 g, 0.5 mmol) in 2 ml of 2-propanol. Then the mixture was heated to 340 K and poured into a solution of La(NO3)3·6H2O (0.216 g, 0.5 mmol) in 5 ml of 2-propanol heated to 340 K. After 10 minutes, the resulting mixture was filtered from sodium nitrate and the filtrate was left in a desiccator above CaCl2 at room temperature. Similar compounds were obtained for Ln3+ = Pr, Nd, Eu, Ho, Tb and Lu.
Crystals of the complexes formed after 1–2 days, were filtered and washed with cooled 2-propanol and dried in air (yield 82-86%). The complexes, as prepared, are soluble in non-polar aprotic solvents, and are less soluble in acetone and La(L)3Phen was recrystallized from a 2-propanol/methanol mixture (5:1, v/v) to give colourless prisms (0.65 g, 0.5 mmol, 84%). 1H NMR (400 MHz, DMSO-d6, 293 K) δ 2.87 (s, 9H, CH3), 2.9 (s, 9H, CH3), 7.32 (t, J = 7.2, 6H, γ-CHphenylamino), 7.57 (t, J = 8, 12H, β-CHphenylamino), 7.62 (d, J = 8.4, 12H, α-CHphenylamino), 7.74 (m, 15H, CH),7.69 (m, 2H, Phen), 7.89 (m, 2H, Phen), 8.41 (d, 2H, Phen), 9.12 (d, 2H, Phen). 31P NMR (400 MHz, DMSO-d6, 290 K) δ 45.1.
Crystalline powder ofIR (KBr pellet, cm−1): 3067 [m, ν (C—Haliph)], 2943 [m, ν (C—Harom)], 2704 [m, ν(C-Harom)], 2660 [w, ν(C—Harom)], 1564 [m, ν(C=N], 1572 [s, ν(S=N)], 1490 (s), 1413 [m, ν(C=C)], 1252 [s, ν(S=O2)], 1243 [m, ν(C—N] + ν(C—C)], 1270 (m), 1164 [ws, ν(P=O)], 1165 [s, ρ(CH3)], 1082 (m), 1030 (m), 990 [m, δ(CCNamine)], 892 [ws, ν(P—N], 874 (ws), 763 (s), 747 (s), 720 (m), 678 (s), 682 (s), 564 (m), 547 (m), 534 (m), 502 (s), 485 (m), 427 (w).
6. Refinement
Crystal data, data collection and structure . All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.96 Å and Uiso(H) = xUeq(C), where x = 1.5 for methyl H and 1.2 for all other H atoms. A rotating-group model was applied for the methyl groups.
details are summarized in Table 2Phenyl ring C1–C6 was refined as disordered over two positions A and B with refined occupancies of 0.50 (3) for both disorder components. The phenyl rings C15–C20, C21–C26 were refined as disordered over two positions with refined occupancies of 0.555 (17) and 0.445 (17), respectively. The bond lenghts C21A—C22A, C22A—C23A, C23A—C24A, C24A—C25A, C25A—C26A, C26A—C21A, C21—C22, C22—C23, C23—C24, C24—C25, C25—C26 and C26—C21 were restrained to have a value of 1.38 (1) Å (using a DFIX restraint). The ring carbon atoms C21A, C26A, C25A, C24A, C23A, C22A as well as C21, C22, C23, C24, C25, C26 were restrained to have planar geometries (within 0.01 Å, using a FLAT restraint). Anisotropic parameters of all C atoms of disordered rings were restrained to have approximately similar values to within 0.01 Å2 (using a SIMU restraint).
During the 3. Satisfactory results (R1 = 5.01%) were obtained modeling disordered C and O atoms, but very large displacement parameters for them were observed. The SQUEEZE procedure (Spek, 2015) implemented in PLATON indicated two solvent cavities each of volume 380 A3, each containing approximately 52 electrons, which corresponds to approximately three molecules of the solvent (2-propanol) per cell. However, the difference in R1 values for the structures with and without the SQUEEZE procedure implemented was rather small (0.5%). In the final the isolated peaks in the solvent-accessible voids were ignored.
several small isolated electron-density peaks were located in solvent-accessible voids that were believed to be solvent molecules. The largest residual electron peak accounted to 0.66 e ÅSupporting information
CCDC reference: 1556367
https://doi.org/10.1107/S2056989017008970/zl2701sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Supporting information file. DOI: https://doi.org/10.1107/S2056989017008970/zl2701Isup4.cdx
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017008970/zl2701Isup6.hkl
hkl-file. DOI: https://doi.org/10.1107/S2056989017008970/zl2701sup5.txt
Data collection: CrysAlis PRO (Agilent, 2016); cell
CrysAlis PRO (Agilent, 2016); data reduction: CrysAlis PRO (Agilent, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).[La(C20H21N3O3PS)3(C12H8N2)] | F(000) = 3208 |
Mr = 1562.39 | Dx = 1.357 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2213 (2) Å | Cell parameters from 14527 reflections |
b = 42.2455 (7) Å | θ = 2.9–27.6° |
c = 15.5956 (3) Å | µ = 0.76 mm−1 |
β = 108.222 (2)° | T = 293 K |
V = 7648.1 (2) Å3 | Block, colourless |
Z = 4 | 0.3 × 0.2 × 0.1 mm |
Agilent Xcalibur Sapphire3 diffractometer | 16526 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 13120 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 16.1827 pixels mm-1 | θmax = 27.7°, θmin = 2.9° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2016) | k = −49→55 |
Tmin = 0.963, Tmax = 1.000 | l = −16→19 |
43241 measured reflections |
Refinement on F2 | 576 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0547P)2 + 4.2326P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.004 |
16526 reflections | Δρmax = 0.66 e Å−3 |
1015 parameters | Δρmin = −0.48 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
La1 | 0.09120 (2) | 0.35503 (2) | 0.43119 (2) | 0.03134 (6) | |
S1 | −0.21614 (8) | 0.34454 (2) | 0.28067 (7) | 0.0450 (2) | |
S2 | −0.00520 (9) | 0.42066 (2) | 0.55977 (7) | 0.0483 (2) | |
S3 | 0.33083 (7) | 0.31661 (2) | 0.61269 (6) | 0.0430 (2) | |
P1 | −0.06748 (9) | 0.36460 (2) | 0.18902 (6) | 0.0439 (2) | |
P2 | 0.15801 (9) | 0.44041 (2) | 0.47608 (7) | 0.0480 (2) | |
P3 | 0.11147 (8) | 0.30133 (2) | 0.61951 (6) | 0.0378 (2) | |
O1 | 0.0235 (2) | 0.37287 (6) | 0.27530 (15) | 0.0435 (6) | |
O2 | 0.1744 (2) | 0.40764 (5) | 0.44636 (17) | 0.0432 (6) | |
O3 | 0.05751 (19) | 0.31109 (5) | 0.52365 (15) | 0.0393 (5) | |
O4 | −0.2988 (2) | 0.31980 (6) | 0.2749 (2) | 0.0610 (8) | |
O5 | −0.1245 (2) | 0.34570 (6) | 0.36742 (17) | 0.0475 (6) | |
O6 | −0.1236 (3) | 0.43021 (9) | 0.5311 (2) | 0.0824 (10) | |
O7 | 0.0112 (2) | 0.38806 (6) | 0.53354 (18) | 0.0522 (7) | |
O8 | 0.4363 (2) | 0.32486 (7) | 0.68112 (19) | 0.0567 (7) | |
O9 | 0.27345 (19) | 0.34382 (6) | 0.55776 (17) | 0.0434 (6) | |
N1 | −0.1691 (3) | 0.34263 (8) | 0.1991 (2) | 0.0484 (8) | |
N2 | 0.0722 (4) | 0.44426 (8) | 0.5338 (3) | 0.0708 (11) | |
N3 | 0.2496 (2) | 0.29808 (7) | 0.6524 (2) | 0.0441 (7) | |
N4 | −0.0168 (3) | 0.34447 (8) | 0.1181 (2) | 0.0544 (8) | |
N5 | −0.1155 (3) | 0.39885 (8) | 0.1385 (2) | 0.0544 (8) | |
N6 | 0.1081 (3) | 0.46540 (7) | 0.3910 (2) | 0.0550 (8) | |
N7 | 0.2845 (3) | 0.45430 (7) | 0.5354 (2) | 0.0581 (9) | |
N8 | 0.0813 (3) | 0.32513 (7) | 0.6930 (2) | 0.0453 (7) | |
N9 | 0.0579 (2) | 0.26692 (7) | 0.63781 (19) | 0.0424 (7) | |
N10 | 0.0939 (3) | 0.30261 (7) | 0.3329 (2) | 0.0427 (7) | |
N11 | 0.2631 (2) | 0.34687 (7) | 0.3593 (2) | 0.0405 (7) | |
C1 | −0.2863 (19) | 0.3812 (3) | 0.2737 (14) | 0.052 (2) | 0.50 (3) |
C2 | −0.3688 (18) | 0.3912 (4) | 0.1948 (12) | 0.061 (2) | 0.50 (3) |
H2 | −0.392524 | 0.377731 | 0.145258 | 0.074* | 0.50 (3) |
C3 | −0.4157 (13) | 0.4214 (4) | 0.1900 (12) | 0.069 (3) | 0.50 (3) |
H3 | −0.470864 | 0.428082 | 0.137292 | 0.083* | 0.50 (3) |
C4 | −0.3802 (13) | 0.4415 (3) | 0.2641 (14) | 0.069 (3) | 0.50 (3) |
H4 | −0.411601 | 0.461676 | 0.260914 | 0.083* | 0.50 (3) |
C5 | −0.2978 (14) | 0.4315 (3) | 0.3429 (12) | 0.068 (3) | 0.50 (3) |
H5 | −0.273998 | 0.444919 | 0.392501 | 0.081* | 0.50 (3) |
C6 | −0.2508 (16) | 0.4013 (4) | 0.3477 (12) | 0.059 (2) | 0.50 (3) |
H6 | −0.195657 | 0.394568 | 0.400468 | 0.070* | 0.50 (3) |
C7 | −0.0699 (4) | 0.31454 (12) | 0.0784 (3) | 0.0752 (14) | |
H7A | −0.104419 | 0.317109 | 0.014435 | 0.113* | |
H7B | −0.128013 | 0.308591 | 0.104901 | 0.113* | |
H7C | −0.012079 | 0.298327 | 0.089899 | 0.113* | |
C8 | 0.0783 (4) | 0.35548 (12) | 0.0932 (3) | 0.0619 (12) | |
C9 | 0.1344 (4) | 0.38299 (14) | 0.1247 (3) | 0.0779 (14) | |
H9 | 0.108845 | 0.395682 | 0.163289 | 0.094* | |
C10 | 0.2290 (5) | 0.39237 (18) | 0.1001 (4) | 0.104 (2) | |
H10 | 0.265300 | 0.411399 | 0.121904 | 0.124* | |
C11 | 0.2698 (6) | 0.3743 (2) | 0.0446 (5) | 0.117 (3) | |
H11 | 0.333153 | 0.380865 | 0.028254 | 0.140* | |
C12 | 0.2173 (6) | 0.3471 (2) | 0.0142 (4) | 0.116 (3) | |
H12 | 0.245607 | 0.334365 | −0.022779 | 0.139* | |
C13 | 0.1217 (5) | 0.33734 (15) | 0.0363 (3) | 0.0872 (17) | |
H13 | 0.085688 | 0.318426 | 0.012907 | 0.105* | |
C14 | −0.0865 (5) | 0.42850 (10) | 0.1906 (3) | 0.0755 (14) | |
H14A | −0.026621 | 0.439343 | 0.174686 | 0.113* | |
H14B | −0.060492 | 0.423703 | 0.253986 | 0.113* | |
H14C | −0.153577 | 0.441758 | 0.177217 | 0.113* | |
C15 | −0.1910 (9) | 0.4014 (3) | 0.0472 (7) | 0.068 (2) | 0.555 (17) |
C20 | −0.2460 (12) | 0.3743 (3) | 0.0040 (9) | 0.083 (2) | 0.555 (17) |
H20 | −0.231449 | 0.354876 | 0.033288 | 0.100* | 0.555 (17) |
C19 | −0.3227 (11) | 0.3763 (2) | −0.0830 (9) | 0.096 (2) | 0.555 (17) |
H19 | −0.359468 | 0.358198 | −0.111961 | 0.115* | 0.555 (17) |
C18 | −0.3444 (10) | 0.4054 (3) | −0.1268 (6) | 0.107 (3) | 0.555 (17) |
H18 | −0.395734 | 0.406726 | −0.185036 | 0.128* | 0.555 (17) |
C17 | −0.2894 (13) | 0.4325 (2) | −0.0836 (6) | 0.109 (3) | 0.555 (17) |
H17 | −0.303983 | 0.451934 | −0.112863 | 0.131* | 0.555 (17) |
C16 | −0.2127 (11) | 0.4305 (3) | 0.0035 (6) | 0.095 (3) | 0.555 (17) |
H16 | −0.175963 | 0.448613 | 0.032386 | 0.114* | 0.555 (17) |
C21 | 0.0248 (11) | 0.4209 (3) | 0.6771 (10) | 0.068 (2) | 0.566 (10) |
C22 | 0.1270 (12) | 0.4307 (3) | 0.7356 (7) | 0.090 (2) | 0.566 (10) |
H22 | 0.184482 | 0.438013 | 0.713144 | 0.108* | 0.566 (10) |
C23 | 0.1468 (12) | 0.4301 (3) | 0.8282 (7) | 0.107 (3) | 0.566 (10) |
H23 | 0.216846 | 0.436944 | 0.867607 | 0.129* | 0.566 (10) |
C24 | 0.0619 (11) | 0.4193 (3) | 0.8606 (8) | 0.104 (3) | 0.566 (10) |
H24 | 0.074303 | 0.418670 | 0.922528 | 0.125* | 0.566 (10) |
C25 | −0.0430 (11) | 0.4093 (2) | 0.8014 (6) | 0.090 (3) | 0.566 (10) |
H25 | −0.100727 | 0.402068 | 0.823759 | 0.108* | 0.566 (10) |
C26 | −0.0615 (11) | 0.4100 (3) | 0.7091 (6) | 0.073 (2) | 0.566 (10) |
H26 | −0.131292 | 0.403255 | 0.669171 | 0.087* | 0.566 (10) |
C27 | −0.0007 (4) | 0.48296 (11) | 0.3751 (4) | 0.0812 (15) | |
H27A | 0.013179 | 0.501705 | 0.411776 | 0.122* | |
H27B | −0.055723 | 0.469828 | 0.390665 | 0.122* | |
H27C | −0.030258 | 0.488795 | 0.312612 | 0.122* | |
C28 | 0.1839 (4) | 0.47542 (10) | 0.3434 (3) | 0.0586 (11) | |
C29 | 0.2027 (6) | 0.50751 (12) | 0.3317 (4) | 0.0901 (18) | |
H29 | 0.162559 | 0.522855 | 0.352467 | 0.108* | |
C30 | 0.2813 (7) | 0.51618 (15) | 0.2891 (4) | 0.113 (2) | |
H30 | 0.293604 | 0.537552 | 0.281054 | 0.136* | |
C31 | 0.3408 (6) | 0.49438 (18) | 0.2589 (4) | 0.107 (2) | |
H31 | 0.394705 | 0.500724 | 0.231459 | 0.128* | |
C32 | 0.3219 (5) | 0.46320 (14) | 0.2685 (4) | 0.0903 (17) | |
H32 | 0.362144 | 0.448145 | 0.246837 | 0.108* | |
C33 | 0.2442 (4) | 0.45371 (11) | 0.3099 (3) | 0.0692 (13) | |
H33 | 0.231681 | 0.432208 | 0.315557 | 0.083* | |
C34 | 0.2921 (5) | 0.48750 (10) | 0.5680 (4) | 0.0888 (17) | |
H34A | 0.226485 | 0.492218 | 0.587097 | 0.133* | |
H34B | 0.293494 | 0.501575 | 0.520006 | 0.133* | |
H34C | 0.361292 | 0.490171 | 0.617880 | 0.133* | |
C35 | 0.3906 (4) | 0.43815 (9) | 0.5492 (3) | 0.0551 (10) | |
C36 | 0.4730 (5) | 0.44964 (13) | 0.5137 (4) | 0.0835 (15) | |
H36 | 0.459842 | 0.468195 | 0.479894 | 0.100* | |
C37 | 0.5769 (5) | 0.43299 (18) | 0.5291 (5) | 0.112 (2) | |
H37 | 0.632723 | 0.440743 | 0.505487 | 0.134* | |
C38 | 0.5972 (5) | 0.40600 (15) | 0.5775 (5) | 0.106 (2) | |
H38 | 0.666582 | 0.395285 | 0.587785 | 0.127* | |
C39 | 0.5164 (5) | 0.39483 (12) | 0.6105 (4) | 0.0897 (18) | |
H39 | 0.529842 | 0.375939 | 0.642704 | 0.108* | |
C40 | 0.4136 (4) | 0.41046 (10) | 0.5981 (3) | 0.0666 (12) | |
H40 | 0.359587 | 0.402268 | 0.622954 | 0.080* | |
C41 | 0.3684 (2) | 0.29128 (6) | 0.53707 (17) | 0.0500 (9) | |
C46 | 0.4646 (2) | 0.29880 (7) | 0.5116 (2) | 0.0720 (13) | |
H46 | 0.508373 | 0.316566 | 0.535733 | 0.086* | |
C45 | 0.4954 (3) | 0.27976 (10) | 0.4502 (2) | 0.097 (2) | |
H45 | 0.559769 | 0.284794 | 0.433180 | 0.117* | |
C44 | 0.4300 (4) | 0.25321 (9) | 0.4142 (2) | 0.095 (2) | |
H44 | 0.450603 | 0.240472 | 0.373076 | 0.114* | |
C43 | 0.3338 (3) | 0.24569 (6) | 0.4396 (2) | 0.0822 (16) | |
H43 | 0.290040 | 0.227922 | 0.415524 | 0.099* | |
C42 | 0.3030 (2) | 0.26472 (6) | 0.5011 (2) | 0.0619 (11) | |
H42 | 0.238643 | 0.259693 | 0.518078 | 0.074* | |
C47 | 0.1695 (4) | 0.34395 (13) | 0.7563 (4) | 0.0796 (15) | |
H47A | 0.202804 | 0.332059 | 0.810680 | 0.119* | |
H47B | 0.135822 | 0.363029 | 0.770168 | 0.119* | |
H47C | 0.228374 | 0.349236 | 0.729899 | 0.119* | |
C48 | −0.0333 (3) | 0.32679 (9) | 0.6974 (3) | 0.0494 (9) | |
C49 | −0.0540 (4) | 0.32713 (12) | 0.7796 (3) | 0.0724 (13) | |
H49 | 0.007602 | 0.326656 | 0.832778 | 0.087* | |
C50 | −0.1649 (5) | 0.32817 (13) | 0.7834 (4) | 0.0881 (18) | |
H50 | −0.177511 | 0.327955 | 0.839206 | 0.106* | |
C51 | −0.2559 (5) | 0.32950 (13) | 0.7070 (5) | 0.0880 (17) | |
H51 | −0.330661 | 0.330433 | 0.710034 | 0.106* | |
C52 | −0.2367 (4) | 0.32944 (12) | 0.6257 (4) | 0.0796 (15) | |
H52 | −0.298956 | 0.330068 | 0.572921 | 0.096* | |
C53 | −0.1264 (3) | 0.32847 (11) | 0.6202 (3) | 0.0609 (11) | |
H53 | −0.114814 | 0.328955 | 0.564068 | 0.073* | |
C54 | 0.1050 (4) | 0.25407 (10) | 0.7293 (3) | 0.0606 (11) | |
H54A | 0.111391 | 0.270699 | 0.772554 | 0.091* | |
H54B | 0.179822 | 0.245223 | 0.736902 | 0.091* | |
H54C | 0.054722 | 0.237855 | 0.738422 | 0.091* | |
C55 | 0.0178 (3) | 0.24399 (9) | 0.5675 (3) | 0.0476 (9) | |
C56 | 0.0768 (4) | 0.21643 (11) | 0.5693 (3) | 0.0686 (12) | |
H56 | 0.143971 | 0.212639 | 0.616564 | 0.082* | |
C57 | 0.0383 (6) | 0.19425 (14) | 0.5025 (4) | 0.102 (2) | |
H57 | 0.079199 | 0.175541 | 0.504696 | 0.123* | |
C58 | −0.0584 (7) | 0.19952 (16) | 0.4338 (5) | 0.106 (2) | |
H58 | −0.083021 | 0.184567 | 0.387985 | 0.127* | |
C59 | −0.1203 (5) | 0.22615 (16) | 0.4302 (4) | 0.098 (2) | |
H59 | −0.187795 | 0.229374 | 0.382725 | 0.118* | |
C60 | −0.0821 (4) | 0.24920 (12) | 0.4990 (3) | 0.0752 (14) | |
H60 | −0.124409 | 0.267603 | 0.497580 | 0.090* | |
C61 | 0.0147 (3) | 0.28047 (9) | 0.3229 (3) | 0.0513 (10) | |
H61 | −0.039745 | 0.282937 | 0.352804 | 0.062* | |
C62 | 0.0086 (4) | 0.25364 (10) | 0.2700 (3) | 0.0646 (12) | |
H62 | −0.047729 | 0.238366 | 0.265593 | 0.077* | |
C63 | 0.0863 (4) | 0.25026 (10) | 0.2250 (3) | 0.0667 (12) | |
H63 | 0.083168 | 0.232540 | 0.188912 | 0.080* | |
C64 | 0.1706 (4) | 0.27301 (9) | 0.2323 (3) | 0.0527 (10) | |
C65 | 0.1723 (3) | 0.29913 (8) | 0.2882 (2) | 0.0410 (8) | |
C66 | 0.2602 (3) | 0.32280 (8) | 0.3012 (2) | 0.0411 (8) | |
C67 | 0.2540 (4) | 0.27103 (11) | 0.1862 (3) | 0.0675 (13) | |
H67 | 0.252659 | 0.253858 | 0.148614 | 0.081* | |
C68 | 0.3341 (4) | 0.29336 (12) | 0.1960 (3) | 0.0654 (12) | |
H68 | 0.386027 | 0.291779 | 0.163506 | 0.078* | |
C69 | 0.3421 (3) | 0.31963 (10) | 0.2552 (3) | 0.0529 (10) | |
C70 | 0.4295 (4) | 0.34229 (12) | 0.2727 (3) | 0.0643 (12) | |
H70 | 0.485326 | 0.341081 | 0.243743 | 0.077* | |
C71 | 0.4331 (4) | 0.36611 (12) | 0.3321 (3) | 0.0668 (12) | |
H71 | 0.491521 | 0.381151 | 0.344738 | 0.080* | |
C72 | 0.3477 (3) | 0.36758 (10) | 0.3734 (3) | 0.0513 (9) | |
H72 | 0.350245 | 0.384125 | 0.413356 | 0.062* | |
C21A | 0.0465 (16) | 0.4224 (4) | 0.6769 (14) | 0.071 (3) | 0.434 (10) |
C26A | −0.0189 (15) | 0.4148 (4) | 0.7314 (9) | 0.083 (3) | 0.434 (10) |
H26A | −0.094691 | 0.408365 | 0.704910 | 0.099* | 0.434 (10) |
C25A | 0.0245 (15) | 0.4165 (3) | 0.8243 (9) | 0.097 (3) | 0.434 (10) |
H25A | −0.020609 | 0.411380 | 0.860486 | 0.117* | 0.434 (10) |
C24A | 0.1374 (15) | 0.4262 (4) | 0.8614 (10) | 0.104 (3) | 0.434 (10) |
H24A | 0.168715 | 0.427479 | 0.923817 | 0.124* | 0.434 (10) |
C23A | 0.2057 (15) | 0.4341 (3) | 0.8077 (8) | 0.108 (3) | 0.434 (10) |
H23A | 0.281472 | 0.440605 | 0.834370 | 0.130* | 0.434 (10) |
C22A | 0.1601 (16) | 0.4321 (4) | 0.7136 (9) | 0.090 (3) | 0.434 (10) |
H22A | 0.204549 | 0.437206 | 0.676840 | 0.108* | 0.434 (10) |
C15A | −0.1797 (13) | 0.4014 (4) | 0.0492 (9) | 0.071 (2) | 0.445 (17) |
C20A | −0.2576 (15) | 0.3789 (4) | 0.0009 (12) | 0.082 (3) | 0.445 (17) |
H20A | −0.269592 | 0.360404 | 0.029188 | 0.098* | 0.445 (17) |
C19A | −0.3177 (13) | 0.3839 (4) | −0.0897 (11) | 0.095 (3) | 0.445 (17) |
H19A | −0.369885 | 0.368863 | −0.122003 | 0.113* | 0.445 (17) |
C18A | −0.2999 (14) | 0.4115 (3) | −0.1320 (8) | 0.104 (3) | 0.445 (17) |
H18A | −0.340084 | 0.414929 | −0.192586 | 0.125* | 0.445 (17) |
C17A | −0.2219 (17) | 0.4341 (3) | −0.0837 (8) | 0.110 (3) | 0.445 (17) |
H17A | −0.209991 | 0.452537 | −0.111978 | 0.132* | 0.445 (17) |
C16A | −0.1618 (13) | 0.4290 (4) | 0.0069 (8) | 0.094 (3) | 0.445 (17) |
H16A | −0.109697 | 0.444079 | 0.039214 | 0.113* | 0.445 (17) |
C1A | −0.291 (2) | 0.3812 (4) | 0.2667 (15) | 0.051 (2) | 0.50 (3) |
C6A | −0.2696 (17) | 0.4040 (4) | 0.3311 (14) | 0.059 (2) | 0.50 (3) |
H6A | −0.216818 | 0.400203 | 0.387686 | 0.071* | 0.50 (3) |
C5A | −0.3249 (16) | 0.4326 (4) | 0.3136 (14) | 0.066 (2) | 0.50 (3) |
H5A | −0.309091 | 0.448419 | 0.357298 | 0.080* | 0.50 (3) |
C4A | −0.4013 (14) | 0.4374 (4) | 0.2331 (14) | 0.068 (3) | 0.50 (3) |
H4A | −0.436112 | 0.457151 | 0.220362 | 0.082* | 0.50 (3) |
C3A | −0.4318 (15) | 0.4140 (4) | 0.1668 (13) | 0.069 (3) | 0.50 (3) |
H3A | −0.489562 | 0.417491 | 0.112337 | 0.083* | 0.50 (3) |
C2A | −0.372 (2) | 0.3851 (4) | 0.1848 (14) | 0.062 (2) | 0.50 (3) |
H2A | −0.388345 | 0.368995 | 0.141959 | 0.074* | 0.50 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
La1 | 0.03289 (10) | 0.02525 (10) | 0.03624 (11) | 0.00223 (8) | 0.01132 (8) | −0.00094 (8) |
S1 | 0.0369 (5) | 0.0413 (5) | 0.0531 (6) | −0.0020 (4) | 0.0089 (4) | −0.0040 (4) |
S2 | 0.0538 (6) | 0.0428 (5) | 0.0527 (6) | 0.0047 (4) | 0.0232 (5) | −0.0101 (4) |
S3 | 0.0305 (4) | 0.0448 (5) | 0.0506 (5) | 0.0031 (4) | 0.0085 (4) | 0.0091 (4) |
P1 | 0.0468 (5) | 0.0455 (5) | 0.0374 (5) | 0.0072 (4) | 0.0104 (4) | −0.0001 (4) |
P2 | 0.0597 (6) | 0.0269 (5) | 0.0628 (6) | 0.0005 (4) | 0.0270 (5) | −0.0064 (4) |
P3 | 0.0339 (5) | 0.0373 (5) | 0.0417 (5) | 0.0020 (4) | 0.0113 (4) | 0.0071 (4) |
O1 | 0.0478 (14) | 0.0413 (14) | 0.0395 (13) | −0.0019 (11) | 0.0110 (11) | 0.0003 (11) |
O2 | 0.0473 (14) | 0.0270 (12) | 0.0589 (16) | −0.0004 (10) | 0.0217 (12) | −0.0065 (11) |
O3 | 0.0356 (12) | 0.0389 (13) | 0.0425 (13) | −0.0003 (10) | 0.0111 (11) | 0.0057 (10) |
O4 | 0.0507 (16) | 0.0509 (16) | 0.078 (2) | −0.0143 (13) | 0.0146 (15) | −0.0070 (14) |
O5 | 0.0393 (14) | 0.0527 (15) | 0.0485 (15) | 0.0005 (12) | 0.0110 (12) | −0.0003 (12) |
O6 | 0.0582 (19) | 0.100 (3) | 0.086 (2) | 0.0177 (18) | 0.0180 (17) | −0.026 (2) |
O7 | 0.0659 (17) | 0.0373 (14) | 0.0642 (17) | −0.0069 (12) | 0.0358 (15) | −0.0131 (12) |
O8 | 0.0359 (14) | 0.0627 (17) | 0.0627 (17) | −0.0036 (13) | 0.0027 (12) | 0.0090 (14) |
O9 | 0.0346 (13) | 0.0367 (13) | 0.0556 (15) | −0.0004 (10) | 0.0092 (11) | 0.0087 (11) |
N1 | 0.0459 (18) | 0.0477 (18) | 0.0462 (18) | 0.0001 (15) | 0.0069 (14) | −0.0087 (15) |
N2 | 0.102 (3) | 0.0347 (18) | 0.102 (3) | −0.0026 (19) | 0.069 (3) | −0.0153 (18) |
N3 | 0.0335 (15) | 0.0462 (17) | 0.0520 (18) | 0.0058 (13) | 0.0121 (14) | 0.0142 (14) |
N4 | 0.055 (2) | 0.063 (2) | 0.0438 (18) | 0.0096 (17) | 0.0137 (16) | −0.0091 (16) |
N5 | 0.064 (2) | 0.0495 (19) | 0.0467 (19) | 0.0114 (16) | 0.0126 (16) | 0.0059 (15) |
N6 | 0.062 (2) | 0.0361 (17) | 0.073 (2) | 0.0105 (15) | 0.0307 (19) | 0.0024 (16) |
N7 | 0.068 (2) | 0.0290 (16) | 0.073 (2) | −0.0048 (16) | 0.0157 (19) | −0.0116 (15) |
N8 | 0.0380 (16) | 0.0492 (18) | 0.0479 (18) | 0.0010 (14) | 0.0123 (14) | −0.0002 (14) |
N9 | 0.0407 (16) | 0.0418 (17) | 0.0419 (17) | −0.0041 (13) | 0.0089 (13) | 0.0083 (13) |
N10 | 0.0463 (17) | 0.0323 (15) | 0.0506 (18) | 0.0006 (13) | 0.0167 (15) | −0.0064 (13) |
N11 | 0.0360 (16) | 0.0400 (16) | 0.0474 (17) | 0.0050 (13) | 0.0155 (13) | −0.0001 (13) |
C1 | 0.039 (4) | 0.051 (4) | 0.065 (5) | 0.001 (3) | 0.013 (4) | −0.001 (4) |
C2 | 0.052 (4) | 0.053 (5) | 0.071 (5) | 0.007 (4) | 0.008 (4) | −0.004 (4) |
C3 | 0.058 (4) | 0.058 (5) | 0.075 (6) | 0.010 (4) | −0.001 (4) | −0.008 (4) |
C4 | 0.061 (5) | 0.055 (4) | 0.078 (6) | 0.016 (4) | 0.003 (5) | −0.017 (4) |
C5 | 0.054 (5) | 0.061 (4) | 0.072 (6) | 0.013 (4) | −0.002 (4) | −0.008 (4) |
C6 | 0.047 (5) | 0.052 (4) | 0.067 (5) | 0.015 (3) | 0.004 (4) | −0.008 (4) |
C7 | 0.086 (4) | 0.072 (3) | 0.063 (3) | 0.011 (3) | 0.017 (3) | −0.025 (2) |
C8 | 0.058 (3) | 0.089 (3) | 0.037 (2) | 0.019 (2) | 0.0115 (19) | −0.001 (2) |
C9 | 0.075 (3) | 0.099 (4) | 0.071 (3) | −0.001 (3) | 0.039 (3) | −0.003 (3) |
C10 | 0.085 (4) | 0.151 (6) | 0.086 (4) | −0.012 (4) | 0.043 (3) | 0.004 (4) |
C11 | 0.084 (5) | 0.201 (9) | 0.077 (4) | 0.008 (5) | 0.043 (4) | 0.006 (5) |
C12 | 0.096 (5) | 0.196 (8) | 0.066 (4) | 0.035 (5) | 0.039 (4) | −0.007 (5) |
C13 | 0.085 (4) | 0.124 (5) | 0.053 (3) | 0.028 (3) | 0.023 (3) | −0.008 (3) |
C14 | 0.097 (4) | 0.047 (3) | 0.078 (3) | 0.011 (3) | 0.022 (3) | 0.004 (2) |
C15 | 0.074 (4) | 0.083 (4) | 0.047 (3) | 0.020 (4) | 0.021 (3) | 0.020 (3) |
C20 | 0.081 (4) | 0.103 (5) | 0.055 (4) | 0.027 (4) | 0.007 (3) | 0.012 (4) |
C19 | 0.097 (4) | 0.118 (5) | 0.059 (4) | 0.020 (4) | 0.005 (4) | 0.016 (4) |
C18 | 0.105 (5) | 0.132 (5) | 0.066 (4) | 0.006 (5) | 0.002 (4) | 0.032 (4) |
C17 | 0.109 (6) | 0.123 (5) | 0.075 (4) | 0.010 (5) | −0.001 (5) | 0.044 (4) |
C16 | 0.097 (5) | 0.104 (4) | 0.068 (4) | 0.012 (5) | 0.001 (4) | 0.036 (4) |
C21 | 0.096 (5) | 0.059 (4) | 0.050 (3) | 0.010 (4) | 0.025 (4) | −0.010 (3) |
C22 | 0.117 (6) | 0.096 (4) | 0.056 (4) | −0.001 (4) | 0.024 (4) | −0.013 (4) |
C23 | 0.135 (6) | 0.119 (4) | 0.064 (5) | −0.006 (5) | 0.026 (4) | −0.011 (4) |
C24 | 0.131 (6) | 0.111 (5) | 0.066 (4) | 0.001 (5) | 0.024 (4) | −0.012 (4) |
C25 | 0.120 (6) | 0.092 (5) | 0.066 (5) | 0.007 (5) | 0.041 (4) | −0.005 (4) |
C26 | 0.105 (6) | 0.069 (4) | 0.053 (4) | 0.009 (4) | 0.038 (4) | −0.010 (3) |
C27 | 0.081 (3) | 0.057 (3) | 0.109 (4) | 0.028 (3) | 0.033 (3) | 0.004 (3) |
C28 | 0.073 (3) | 0.044 (2) | 0.061 (3) | 0.009 (2) | 0.024 (2) | 0.0064 (19) |
C29 | 0.143 (5) | 0.052 (3) | 0.093 (4) | 0.007 (3) | 0.062 (4) | 0.013 (3) |
C30 | 0.188 (7) | 0.068 (4) | 0.108 (5) | −0.018 (4) | 0.081 (5) | 0.017 (3) |
C31 | 0.131 (6) | 0.113 (5) | 0.100 (5) | −0.008 (5) | 0.069 (4) | 0.013 (4) |
C32 | 0.107 (4) | 0.084 (4) | 0.097 (4) | 0.012 (3) | 0.058 (4) | 0.014 (3) |
C33 | 0.082 (3) | 0.050 (3) | 0.086 (3) | 0.011 (2) | 0.041 (3) | 0.010 (2) |
C34 | 0.109 (4) | 0.039 (2) | 0.111 (4) | −0.013 (3) | 0.025 (4) | −0.032 (3) |
C35 | 0.059 (3) | 0.041 (2) | 0.061 (3) | −0.0118 (19) | 0.012 (2) | −0.0073 (18) |
C36 | 0.079 (4) | 0.073 (3) | 0.098 (4) | −0.018 (3) | 0.028 (3) | 0.012 (3) |
C37 | 0.075 (4) | 0.123 (6) | 0.147 (6) | −0.034 (4) | 0.050 (4) | −0.022 (5) |
C38 | 0.060 (3) | 0.073 (4) | 0.167 (7) | −0.006 (3) | 0.010 (4) | −0.018 (4) |
C39 | 0.067 (3) | 0.058 (3) | 0.118 (5) | −0.005 (3) | −0.008 (3) | 0.004 (3) |
C40 | 0.064 (3) | 0.049 (3) | 0.078 (3) | −0.013 (2) | 0.009 (2) | −0.003 (2) |
C41 | 0.045 (2) | 0.053 (2) | 0.053 (2) | 0.0169 (18) | 0.0167 (18) | 0.0167 (19) |
C46 | 0.053 (3) | 0.094 (4) | 0.074 (3) | 0.016 (3) | 0.027 (2) | 0.014 (3) |
C45 | 0.083 (4) | 0.134 (6) | 0.089 (4) | 0.051 (4) | 0.049 (3) | 0.029 (4) |
C44 | 0.126 (5) | 0.088 (4) | 0.079 (4) | 0.061 (4) | 0.043 (4) | 0.017 (3) |
C43 | 0.111 (4) | 0.058 (3) | 0.074 (3) | 0.032 (3) | 0.023 (3) | 0.008 (3) |
C42 | 0.072 (3) | 0.046 (2) | 0.069 (3) | 0.015 (2) | 0.024 (2) | 0.009 (2) |
C47 | 0.067 (3) | 0.085 (3) | 0.080 (3) | −0.004 (3) | 0.014 (3) | −0.036 (3) |
C48 | 0.050 (2) | 0.045 (2) | 0.057 (2) | 0.0090 (18) | 0.0228 (19) | 0.0061 (18) |
C49 | 0.075 (3) | 0.085 (3) | 0.066 (3) | 0.023 (3) | 0.035 (3) | 0.016 (3) |
C50 | 0.099 (4) | 0.097 (4) | 0.094 (4) | 0.035 (3) | 0.068 (4) | 0.031 (3) |
C51 | 0.076 (4) | 0.086 (4) | 0.124 (5) | 0.016 (3) | 0.063 (4) | 0.021 (4) |
C52 | 0.046 (3) | 0.089 (4) | 0.106 (4) | 0.011 (3) | 0.027 (3) | 0.004 (3) |
C53 | 0.045 (2) | 0.074 (3) | 0.066 (3) | 0.008 (2) | 0.020 (2) | 0.005 (2) |
C54 | 0.074 (3) | 0.055 (2) | 0.045 (2) | −0.013 (2) | 0.007 (2) | 0.0161 (19) |
C55 | 0.045 (2) | 0.048 (2) | 0.048 (2) | −0.0138 (18) | 0.0132 (18) | 0.0088 (17) |
C56 | 0.082 (3) | 0.052 (3) | 0.066 (3) | −0.007 (2) | 0.015 (3) | −0.006 (2) |
C57 | 0.139 (6) | 0.065 (4) | 0.094 (5) | −0.010 (4) | 0.024 (4) | −0.017 (3) |
C58 | 0.136 (6) | 0.078 (4) | 0.088 (5) | −0.045 (4) | 0.013 (4) | −0.008 (3) |
C59 | 0.087 (4) | 0.109 (5) | 0.069 (3) | −0.043 (4) | −0.019 (3) | 0.020 (3) |
C60 | 0.062 (3) | 0.077 (3) | 0.071 (3) | −0.024 (3) | −0.001 (2) | 0.018 (3) |
C61 | 0.057 (2) | 0.038 (2) | 0.060 (2) | −0.0045 (18) | 0.020 (2) | −0.0070 (18) |
C62 | 0.072 (3) | 0.045 (2) | 0.073 (3) | −0.015 (2) | 0.018 (2) | −0.019 (2) |
C63 | 0.081 (3) | 0.047 (2) | 0.068 (3) | 0.003 (2) | 0.016 (3) | −0.021 (2) |
C64 | 0.059 (2) | 0.046 (2) | 0.052 (2) | 0.0152 (19) | 0.014 (2) | −0.0069 (18) |
C65 | 0.044 (2) | 0.0394 (19) | 0.0393 (19) | 0.0107 (16) | 0.0125 (16) | −0.0010 (15) |
C66 | 0.0388 (19) | 0.045 (2) | 0.0416 (19) | 0.0129 (16) | 0.0157 (16) | 0.0020 (16) |
C67 | 0.077 (3) | 0.064 (3) | 0.063 (3) | 0.017 (3) | 0.024 (2) | −0.019 (2) |
C68 | 0.063 (3) | 0.084 (3) | 0.056 (3) | 0.025 (3) | 0.029 (2) | −0.007 (2) |
C69 | 0.047 (2) | 0.063 (3) | 0.051 (2) | 0.016 (2) | 0.0197 (19) | 0.004 (2) |
C70 | 0.048 (2) | 0.080 (3) | 0.073 (3) | 0.010 (2) | 0.031 (2) | 0.004 (3) |
C71 | 0.045 (2) | 0.074 (3) | 0.086 (3) | −0.006 (2) | 0.026 (2) | 0.002 (3) |
C72 | 0.042 (2) | 0.049 (2) | 0.065 (3) | −0.0010 (18) | 0.0197 (19) | −0.0051 (19) |
C21A | 0.102 (6) | 0.063 (4) | 0.051 (4) | 0.012 (4) | 0.027 (4) | −0.012 (4) |
C26A | 0.114 (6) | 0.082 (4) | 0.056 (4) | 0.011 (4) | 0.031 (4) | −0.010 (4) |
C25A | 0.128 (6) | 0.101 (5) | 0.061 (5) | 0.003 (5) | 0.028 (5) | −0.013 (4) |
C24A | 0.134 (6) | 0.116 (5) | 0.061 (5) | −0.006 (5) | 0.031 (5) | −0.006 (4) |
C23A | 0.132 (7) | 0.119 (5) | 0.067 (5) | −0.009 (6) | 0.024 (5) | −0.013 (5) |
C22A | 0.119 (6) | 0.095 (5) | 0.051 (5) | −0.002 (5) | 0.021 (4) | −0.013 (4) |
C15A | 0.076 (4) | 0.086 (4) | 0.051 (4) | 0.020 (4) | 0.017 (4) | 0.019 (4) |
C20A | 0.083 (4) | 0.098 (5) | 0.054 (4) | 0.024 (4) | 0.007 (4) | 0.018 (4) |
C19A | 0.096 (4) | 0.113 (5) | 0.059 (4) | 0.019 (5) | 0.002 (4) | 0.020 (4) |
C18A | 0.108 (5) | 0.128 (5) | 0.062 (4) | 0.006 (5) | 0.006 (5) | 0.032 (4) |
C17A | 0.108 (6) | 0.127 (5) | 0.077 (4) | 0.006 (5) | 0.003 (5) | 0.038 (4) |
C16A | 0.093 (5) | 0.109 (5) | 0.067 (4) | 0.010 (5) | 0.006 (5) | 0.033 (4) |
C1A | 0.039 (4) | 0.050 (4) | 0.063 (4) | 0.002 (3) | 0.015 (4) | −0.003 (3) |
C6A | 0.049 (5) | 0.057 (4) | 0.065 (5) | 0.009 (4) | 0.009 (4) | −0.005 (4) |
C5A | 0.056 (5) | 0.061 (4) | 0.069 (6) | 0.015 (4) | 0.000 (4) | −0.012 (4) |
C4A | 0.061 (5) | 0.058 (4) | 0.076 (6) | 0.015 (4) | 0.008 (5) | −0.012 (4) |
C3A | 0.060 (4) | 0.056 (5) | 0.079 (6) | 0.013 (4) | 0.003 (4) | −0.005 (4) |
C2A | 0.052 (4) | 0.054 (4) | 0.071 (5) | 0.009 (4) | 0.008 (4) | −0.002 (4) |
La1—O1 | 2.430 (2) | C31—C32 | 1.354 (8) |
La1—O2 | 2.424 (2) | C32—H32 | 0.9300 |
La1—O3 | 2.463 (2) | C32—C33 | 1.364 (7) |
La1—O5 | 2.541 (2) | C33—H33 | 0.9300 |
La1—O7 | 2.535 (2) | C34—H34A | 0.9600 |
La1—O9 | 2.516 (2) | C34—H34B | 0.9600 |
La1—N10 | 2.699 (3) | C34—H34C | 0.9600 |
La1—N11 | 2.695 (3) | C35—C36 | 1.380 (6) |
S1—O4 | 1.436 (3) | C35—C40 | 1.377 (6) |
S1—O5 | 1.462 (3) | C36—H36 | 0.9300 |
S1—N1 | 1.553 (3) | C36—C37 | 1.406 (8) |
S1—C1 | 1.756 (10) | C37—H37 | 0.9300 |
S1—C1A | 1.778 (13) | C37—C38 | 1.347 (9) |
S2—O6 | 1.432 (3) | C38—H38 | 0.9300 |
S2—O7 | 1.468 (2) | C38—C39 | 1.334 (8) |
S2—N2 | 1.514 (4) | C39—H39 | 0.9300 |
S2—C21 | 1.751 (16) | C39—C40 | 1.379 (7) |
S2—C21A | 1.74 (2) | C40—H40 | 0.9300 |
S3—O8 | 1.436 (3) | C41—C46 | 1.3900 |
S3—O9 | 1.474 (2) | C41—C42 | 1.3900 |
S3—N3 | 1.538 (3) | C46—H46 | 0.9300 |
S3—C41 | 1.756 (2) | C46—C45 | 1.3900 |
P1—O1 | 1.494 (2) | C45—H45 | 0.9300 |
P1—N1 | 1.597 (3) | C45—C44 | 1.3900 |
P1—N4 | 1.661 (3) | C44—H44 | 0.9300 |
P1—N5 | 1.664 (3) | C44—C43 | 1.3900 |
P2—O2 | 1.493 (2) | C43—H43 | 0.9300 |
P2—N2 | 1.590 (4) | C43—C42 | 1.3900 |
P2—N6 | 1.656 (3) | C42—H42 | 0.9300 |
P2—N7 | 1.642 (4) | C47—H47A | 0.9600 |
P3—O3 | 1.491 (2) | C47—H47B | 0.9600 |
P3—N3 | 1.610 (3) | C47—H47C | 0.9600 |
P3—N8 | 1.651 (3) | C48—C49 | 1.382 (6) |
P3—N9 | 1.655 (3) | C48—C53 | 1.375 (5) |
N4—C7 | 1.467 (6) | C49—H49 | 0.9300 |
N4—C8 | 1.414 (6) | C49—C50 | 1.376 (7) |
N5—C14 | 1.475 (5) | C50—H50 | 0.9300 |
N5—C15 | 1.437 (9) | C50—C51 | 1.353 (8) |
N5—C15A | 1.372 (11) | C51—H51 | 0.9300 |
N6—C27 | 1.474 (5) | C51—C52 | 1.360 (7) |
N6—C28 | 1.421 (5) | C52—H52 | 0.9300 |
N7—C34 | 1.484 (5) | C52—C53 | 1.378 (6) |
N7—C35 | 1.421 (5) | C53—H53 | 0.9300 |
N8—C47 | 1.451 (5) | C54—H54A | 0.9600 |
N8—C48 | 1.424 (5) | C54—H54B | 0.9600 |
N9—C54 | 1.466 (4) | C54—H54C | 0.9600 |
N9—C55 | 1.430 (5) | C55—C56 | 1.365 (6) |
N10—C61 | 1.320 (4) | C55—C60 | 1.365 (5) |
N10—C65 | 1.358 (4) | C56—H56 | 0.9300 |
N11—C66 | 1.355 (4) | C56—C57 | 1.371 (7) |
N11—C72 | 1.319 (5) | C57—H57 | 0.9300 |
C1—C2 | 1.3900 | C57—C58 | 1.342 (8) |
C1—C6 | 1.3900 | C58—H58 | 0.9300 |
C2—H2 | 0.9300 | C58—C59 | 1.347 (9) |
C2—C3 | 1.3900 | C59—H59 | 0.9300 |
C3—H3 | 0.9300 | C59—C60 | 1.416 (7) |
C3—C4 | 1.3900 | C60—H60 | 0.9300 |
C4—H4 | 0.9300 | C61—H61 | 0.9300 |
C4—C5 | 1.3900 | C61—C62 | 1.390 (5) |
C5—H5 | 0.9300 | C62—H62 | 0.9300 |
C5—C6 | 1.3900 | C62—C63 | 1.354 (6) |
C6—H6 | 0.9300 | C63—H63 | 0.9300 |
C7—H7A | 0.9600 | C63—C64 | 1.387 (6) |
C7—H7B | 0.9600 | C64—C65 | 1.402 (5) |
C7—H7C | 0.9600 | C64—C67 | 1.421 (6) |
C8—C9 | 1.360 (7) | C65—C66 | 1.435 (5) |
C8—C13 | 1.398 (6) | C66—C69 | 1.408 (5) |
C9—H9 | 0.9300 | C67—H67 | 0.9300 |
C9—C10 | 1.385 (7) | C67—C68 | 1.334 (6) |
C10—H10 | 0.9300 | C68—H68 | 0.9300 |
C10—C11 | 1.360 (9) | C68—C69 | 1.427 (6) |
C11—H11 | 0.9300 | C69—C70 | 1.396 (6) |
C11—C12 | 1.330 (10) | C70—H70 | 0.9300 |
C12—H12 | 0.9300 | C70—C71 | 1.359 (6) |
C12—C13 | 1.380 (9) | C71—H71 | 0.9300 |
C13—H13 | 0.9300 | C71—C72 | 1.389 (6) |
C14—H14A | 0.9600 | C72—H72 | 0.9300 |
C14—H14B | 0.9600 | C21A—C26A | 1.373 (9) |
C14—H14C | 0.9600 | C21A—C22A | 1.389 (9) |
C15—C20 | 1.3900 | C26A—H26A | 0.9300 |
C15—C16 | 1.3900 | C26A—C25A | 1.379 (9) |
C20—H20 | 0.9300 | C25A—H25A | 0.9300 |
C20—C19 | 1.3900 | C25A—C24A | 1.380 (9) |
C19—H19 | 0.9300 | C24A—H24A | 0.9300 |
C19—C18 | 1.3900 | C24A—C23A | 1.396 (9) |
C18—H18 | 0.9300 | C23A—H23A | 0.9300 |
C18—C17 | 1.3900 | C23A—C22A | 1.399 (9) |
C17—H17 | 0.9300 | C22A—H22A | 0.9300 |
C17—C16 | 1.3900 | C15A—C20A | 1.3900 |
C16—H16 | 0.9300 | C15A—C16A | 1.3900 |
C21—C22 | 1.361 (9) | C20A—H20A | 0.9300 |
C21—C26 | 1.379 (8) | C20A—C19A | 1.3900 |
C22—H22 | 0.9300 | C19A—H19A | 0.9300 |
C22—C23 | 1.387 (8) | C19A—C18A | 1.3900 |
C23—H23 | 0.9300 | C18A—H18A | 0.9300 |
C23—C24 | 1.367 (9) | C18A—C17A | 1.3900 |
C24—H24 | 0.9300 | C17A—H17A | 0.9300 |
C24—C25 | 1.391 (9) | C17A—C16A | 1.3900 |
C25—H25 | 0.9300 | C16A—H16A | 0.9300 |
C25—C26 | 1.386 (8) | C1A—C6A | 1.358 (12) |
C26—H26 | 0.9300 | C1A—C2A | 1.360 (12) |
C27—H27A | 0.9600 | C6A—H6A | 0.9300 |
C27—H27B | 0.9600 | C6A—C5A | 1.370 (14) |
C27—H27C | 0.9600 | C5A—H5A | 0.9300 |
C28—C29 | 1.396 (6) | C5A—C4A | 1.324 (14) |
C28—C33 | 1.377 (6) | C4A—H4A | 0.9300 |
C29—H29 | 0.9300 | C4A—C3A | 1.394 (14) |
C29—C30 | 1.378 (8) | C3A—H3A | 0.9300 |
C30—H30 | 0.9300 | C3A—C2A | 1.405 (14) |
C30—C31 | 1.346 (8) | C2A—H2A | 0.9300 |
C31—H31 | 0.9300 | ||
O1—La1—O3 | 138.81 (8) | C33—C28—C29 | 117.9 (5) |
O1—La1—O5 | 70.70 (8) | C28—C29—H29 | 120.4 |
O1—La1—O7 | 112.43 (9) | C30—C29—C28 | 119.3 (5) |
O1—La1—O9 | 141.64 (8) | C30—C29—H29 | 120.4 |
O1—La1—N10 | 75.35 (8) | C29—C30—H30 | 119.3 |
O1—La1—N11 | 71.91 (8) | C31—C30—C29 | 121.4 (6) |
O2—La1—O1 | 79.32 (8) | C31—C30—H30 | 119.3 |
O2—La1—O3 | 140.85 (8) | C30—C31—H31 | 120.1 |
O2—La1—O5 | 122.18 (8) | C30—C31—C32 | 119.8 (6) |
O2—La1—O7 | 70.52 (8) | C32—C31—H31 | 120.1 |
O2—La1—O9 | 81.65 (8) | C31—C32—H32 | 119.8 |
O2—La1—N10 | 136.74 (8) | C31—C32—C33 | 120.4 (5) |
O2—La1—N11 | 78.48 (8) | C33—C32—H32 | 119.8 |
O3—La1—O5 | 76.66 (8) | C28—C33—H33 | 119.4 |
O3—La1—O7 | 83.00 (8) | C32—C33—C28 | 121.2 (5) |
O3—La1—O9 | 70.60 (7) | C32—C33—H33 | 119.4 |
O3—La1—N10 | 75.41 (9) | N7—C34—H34A | 109.5 |
O3—La1—N11 | 116.22 (8) | N7—C34—H34B | 109.5 |
O5—La1—N10 | 81.14 (9) | N7—C34—H34C | 109.5 |
O5—La1—N11 | 131.75 (8) | H34A—C34—H34B | 109.5 |
O7—La1—O5 | 76.97 (8) | H34A—C34—H34C | 109.5 |
O7—La1—N10 | 152.22 (9) | H34B—C34—H34C | 109.5 |
O7—La1—N11 | 146.79 (9) | C36—C35—N7 | 121.1 (4) |
O9—La1—O5 | 146.45 (8) | C40—C35—N7 | 120.7 (4) |
O9—La1—O7 | 91.76 (9) | C40—C35—C36 | 118.3 (5) |
O9—La1—N10 | 97.23 (9) | C35—C36—H36 | 120.4 |
O9—La1—N11 | 71.83 (8) | C35—C36—C37 | 119.3 (5) |
N11—La1—N10 | 60.60 (9) | C37—C36—H36 | 120.4 |
O4—S1—O5 | 113.73 (17) | C36—C37—H37 | 119.4 |
O4—S1—N1 | 110.09 (18) | C38—C37—C36 | 121.2 (6) |
O4—S1—C1 | 108.5 (9) | C38—C37—H37 | 119.4 |
O4—S1—C1A | 107.5 (9) | C37—C38—H38 | 120.4 |
O5—S1—N1 | 112.78 (16) | C39—C38—C37 | 119.2 (6) |
O5—S1—C1 | 104.2 (6) | C39—C38—H38 | 120.4 |
O5—S1—C1A | 107.5 (7) | C38—C39—H39 | 119.0 |
N1—S1—C1 | 107.1 (9) | C38—C39—C40 | 121.9 (5) |
N1—S1—C1A | 104.7 (9) | C40—C39—H39 | 119.0 |
O6—S2—O7 | 112.93 (19) | C35—C40—C39 | 120.2 (5) |
O6—S2—N2 | 112.7 (2) | C35—C40—H40 | 119.9 |
O6—S2—C21 | 100.7 (5) | C39—C40—H40 | 119.9 |
O6—S2—C21A | 108.4 (6) | C46—C41—S3 | 118.33 (18) |
O7—S2—N2 | 113.08 (17) | C46—C41—C42 | 120.0 |
O7—S2—C21 | 107.1 (5) | C42—C41—S3 | 121.66 (18) |
O7—S2—C21A | 107.2 (6) | C41—C46—H46 | 120.0 |
N2—S2—C21 | 109.4 (5) | C45—C46—C41 | 120.0 |
N2—S2—C21A | 101.6 (6) | C45—C46—H46 | 120.0 |
O8—S3—O9 | 113.33 (16) | C46—C45—H45 | 120.0 |
O8—S3—N3 | 111.49 (17) | C46—C45—C44 | 120.0 |
O8—S3—C41 | 106.54 (16) | C44—C45—H45 | 120.0 |
O9—S3—N3 | 112.43 (15) | C45—C44—H44 | 120.0 |
O9—S3—C41 | 105.18 (14) | C43—C44—C45 | 120.0 |
N3—S3—C41 | 107.32 (16) | C43—C44—H44 | 120.0 |
O1—P1—N1 | 115.44 (15) | C44—C43—H43 | 120.0 |
O1—P1—N4 | 113.08 (16) | C44—C43—C42 | 120.0 |
O1—P1—N5 | 106.05 (16) | C42—C43—H43 | 120.0 |
N1—P1—N4 | 103.39 (18) | C41—C42—H42 | 120.0 |
N1—P1—N5 | 112.44 (18) | C43—C42—C41 | 120.0 |
N4—P1—N5 | 106.21 (17) | C43—C42—H42 | 120.0 |
O2—P2—N2 | 116.54 (16) | N8—C47—H47A | 109.5 |
O2—P2—N6 | 113.21 (16) | N8—C47—H47B | 109.5 |
O2—P2—N7 | 108.21 (16) | N8—C47—H47C | 109.5 |
N2—P2—N6 | 104.24 (19) | H47A—C47—H47B | 109.5 |
N2—P2—N7 | 108.4 (2) | H47A—C47—H47C | 109.5 |
N7—P2—N6 | 105.63 (18) | H47B—C47—H47C | 109.5 |
O3—P3—N3 | 115.74 (15) | C49—C48—N8 | 120.8 (4) |
O3—P3—N8 | 113.77 (15) | C53—C48—N8 | 121.2 (4) |
O3—P3—N9 | 109.94 (14) | C53—C48—C49 | 118.0 (4) |
N3—P3—N8 | 105.68 (16) | C48—C49—H49 | 119.7 |
N3—P3—N9 | 107.60 (15) | C50—C49—C48 | 120.6 (5) |
N8—P3—N9 | 103.20 (16) | C50—C49—H49 | 119.7 |
P1—O1—La1 | 138.87 (14) | C49—C50—H50 | 119.6 |
P2—O2—La1 | 141.94 (14) | C51—C50—C49 | 120.8 (5) |
P3—O3—La1 | 133.87 (13) | C51—C50—H50 | 119.6 |
S1—O5—La1 | 140.15 (15) | C50—C51—H51 | 120.4 |
S2—O7—La1 | 143.59 (15) | C50—C51—C52 | 119.1 (5) |
S3—O9—La1 | 138.28 (14) | C52—C51—H51 | 120.4 |
S1—N1—P1 | 123.3 (2) | C51—C52—H52 | 119.5 |
S2—N2—P2 | 131.5 (2) | C51—C52—C53 | 121.0 (5) |
S3—N3—P3 | 124.93 (19) | C53—C52—H52 | 119.5 |
C7—N4—P1 | 120.9 (3) | C48—C53—C52 | 120.4 (4) |
C8—N4—P1 | 121.6 (3) | C48—C53—H53 | 119.8 |
C8—N4—C7 | 117.5 (4) | C52—C53—H53 | 119.8 |
C14—N5—P1 | 119.2 (3) | N9—C54—H54A | 109.5 |
C15—N5—P1 | 123.8 (6) | N9—C54—H54B | 109.5 |
C15—N5—C14 | 116.8 (6) | N9—C54—H54C | 109.5 |
C15A—N5—P1 | 123.7 (8) | H54A—C54—H54B | 109.5 |
C15A—N5—C14 | 117.1 (8) | H54A—C54—H54C | 109.5 |
C27—N6—P2 | 122.8 (3) | H54B—C54—H54C | 109.5 |
C28—N6—P2 | 118.2 (3) | C56—C55—N9 | 120.7 (4) |
C28—N6—C27 | 117.6 (4) | C56—C55—C60 | 119.4 (4) |
C34—N7—P2 | 118.5 (3) | C60—C55—N9 | 119.9 (4) |
C35—N7—P2 | 124.6 (3) | C55—C56—H56 | 119.5 |
C35—N7—C34 | 116.5 (4) | C55—C56—C57 | 120.9 (5) |
C47—N8—P3 | 121.7 (3) | C57—C56—H56 | 119.5 |
C48—N8—P3 | 120.0 (3) | C56—C57—H57 | 120.0 |
C48—N8—C47 | 118.3 (3) | C58—C57—C56 | 120.0 (6) |
C54—N9—P3 | 115.9 (2) | C58—C57—H57 | 120.0 |
C55—N9—P3 | 121.4 (2) | C57—C58—H58 | 119.5 |
C55—N9—C54 | 115.6 (3) | C57—C58—C59 | 121.0 (6) |
C61—N10—La1 | 120.6 (2) | C59—C58—H58 | 119.5 |
C61—N10—C65 | 118.2 (3) | C58—C59—H59 | 120.2 |
C65—N10—La1 | 121.1 (2) | C58—C59—C60 | 119.7 (5) |
C66—N11—La1 | 120.9 (2) | C60—C59—H59 | 120.2 |
C72—N11—La1 | 121.2 (2) | C55—C60—C59 | 119.0 (5) |
C72—N11—C66 | 117.7 (3) | C55—C60—H60 | 120.5 |
C2—C1—S1 | 121.9 (10) | C59—C60—H60 | 120.5 |
C2—C1—C6 | 120.0 | N10—C61—H61 | 118.3 |
C6—C1—S1 | 117.9 (10) | N10—C61—C62 | 123.3 (4) |
C1—C2—H2 | 120.0 | C62—C61—H61 | 118.3 |
C3—C2—C1 | 120.0 | C61—C62—H62 | 120.7 |
C3—C2—H2 | 120.0 | C63—C62—C61 | 118.5 (4) |
C2—C3—H3 | 120.0 | C63—C62—H62 | 120.7 |
C4—C3—C2 | 120.0 | C62—C63—H63 | 119.7 |
C4—C3—H3 | 120.0 | C62—C63—C64 | 120.5 (4) |
C3—C4—H4 | 120.0 | C64—C63—H63 | 119.7 |
C3—C4—C5 | 120.0 | C63—C64—C65 | 117.6 (4) |
C5—C4—H4 | 120.0 | C63—C64—C67 | 123.3 (4) |
C4—C5—H5 | 120.0 | C65—C64—C67 | 119.1 (4) |
C4—C5—C6 | 120.0 | N10—C65—C64 | 121.9 (3) |
C6—C5—H5 | 120.0 | N10—C65—C66 | 118.0 (3) |
C1—C6—H6 | 120.0 | C64—C65—C66 | 120.1 (3) |
C5—C6—C1 | 120.0 | N11—C66—C65 | 118.6 (3) |
C5—C6—H6 | 120.0 | N11—C66—C69 | 122.5 (3) |
N4—C7—H7A | 109.5 | C69—C66—C65 | 118.8 (3) |
N4—C7—H7B | 109.5 | C64—C67—H67 | 119.4 |
N4—C7—H7C | 109.5 | C68—C67—C64 | 121.2 (4) |
H7A—C7—H7B | 109.5 | C68—C67—H67 | 119.4 |
H7A—C7—H7C | 109.5 | C67—C68—H68 | 119.2 |
H7B—C7—H7C | 109.5 | C67—C68—C69 | 121.5 (4) |
C9—C8—N4 | 123.2 (4) | C69—C68—H68 | 119.2 |
C9—C8—C13 | 116.7 (5) | C66—C69—C68 | 119.2 (4) |
C13—C8—N4 | 120.1 (5) | C70—C69—C66 | 117.2 (4) |
C8—C9—H9 | 119.5 | C70—C69—C68 | 123.6 (4) |
C8—C9—C10 | 121.0 (5) | C69—C70—H70 | 120.0 |
C10—C9—H9 | 119.5 | C71—C70—C69 | 120.0 (4) |
C9—C10—H10 | 119.3 | C71—C70—H70 | 120.0 |
C11—C10—C9 | 121.3 (7) | C70—C71—H71 | 120.6 |
C11—C10—H10 | 119.3 | C70—C71—C72 | 118.7 (4) |
C10—C11—H11 | 120.6 | C72—C71—H71 | 120.6 |
C12—C11—C10 | 118.7 (7) | N11—C72—C71 | 123.8 (4) |
C12—C11—H11 | 120.6 | N11—C72—H72 | 118.1 |
C11—C12—H12 | 119.3 | C71—C72—H72 | 118.1 |
C11—C12—C13 | 121.3 (7) | C26A—C21A—S2 | 123.4 (13) |
C13—C12—H12 | 119.3 | C26A—C21A—C22A | 120.9 (17) |
C8—C13—H13 | 119.5 | C22A—C21A—S2 | 115.7 (12) |
C12—C13—C8 | 121.0 (6) | C21A—C26A—H26A | 119.0 |
C12—C13—H13 | 119.5 | C21A—C26A—C25A | 122.1 (16) |
N5—C14—H14A | 109.5 | C25A—C26A—H26A | 119.0 |
N5—C14—H14B | 109.5 | C26A—C25A—H25A | 121.3 |
N5—C14—H14C | 109.5 | C26A—C25A—C24A | 117.4 (15) |
H14A—C14—H14B | 109.5 | C24A—C25A—H25A | 121.3 |
H14A—C14—H14C | 109.5 | C25A—C24A—H24A | 119.1 |
H14B—C14—H14C | 109.5 | C25A—C24A—C23A | 121.8 (15) |
C20—C15—N5 | 118.8 (8) | C23A—C24A—H24A | 119.1 |
C20—C15—C16 | 120.0 | C24A—C23A—H23A | 120.1 |
C16—C15—N5 | 121.2 (8) | C24A—C23A—C22A | 119.9 (15) |
C15—C20—H20 | 120.0 | C22A—C23A—H23A | 120.1 |
C15—C20—C19 | 120.0 | C21A—C22A—C23A | 118.0 (16) |
C19—C20—H20 | 120.0 | C21A—C22A—H22A | 121.0 |
C20—C19—H19 | 120.0 | C23A—C22A—H22A | 121.0 |
C18—C19—C20 | 120.0 | N5—C15A—C20A | 125.0 (11) |
C18—C19—H19 | 120.0 | N5—C15A—C16A | 115.0 (11) |
C19—C18—H18 | 120.0 | C20A—C15A—C16A | 120.0 |
C17—C18—C19 | 120.0 | C15A—C20A—H20A | 120.0 |
C17—C18—H18 | 120.0 | C19A—C20A—C15A | 120.0 |
C18—C17—H17 | 120.0 | C19A—C20A—H20A | 120.0 |
C18—C17—C16 | 120.0 | C20A—C19A—H19A | 120.0 |
C16—C17—H17 | 120.0 | C20A—C19A—C18A | 120.0 |
C15—C16—H16 | 120.0 | C18A—C19A—H19A | 120.0 |
C17—C16—C15 | 120.0 | C19A—C18A—H18A | 120.0 |
C17—C16—H16 | 120.0 | C17A—C18A—C19A | 120.0 |
C22—C21—S2 | 123.4 (10) | C17A—C18A—H18A | 120.0 |
C22—C21—C26 | 120.3 (13) | C18A—C17A—H17A | 120.0 |
C26—C21—S2 | 116.2 (9) | C18A—C17A—C16A | 120.0 |
C21—C22—H22 | 119.5 | C16A—C17A—H17A | 120.0 |
C21—C22—C23 | 121.1 (12) | C15A—C16A—H16A | 120.0 |
C23—C22—H22 | 119.5 | C17A—C16A—C15A | 120.0 |
C22—C23—H23 | 120.5 | C17A—C16A—H16A | 120.0 |
C24—C23—C22 | 119.0 (12) | C6A—C1A—S1 | 123.7 (13) |
C24—C23—H23 | 120.5 | C6A—C1A—C2A | 121.6 (9) |
C23—C24—H24 | 119.8 | C2A—C1A—S1 | 114.7 (12) |
C23—C24—C25 | 120.3 (12) | C1A—C6A—H6A | 119.7 |
C25—C24—H24 | 119.8 | C1A—C6A—C5A | 120.6 (10) |
C24—C25—H25 | 120.0 | C5A—C6A—H6A | 119.7 |
C26—C25—C24 | 119.9 (11) | C6A—C5A—H5A | 120.6 |
C26—C25—H25 | 120.0 | C4A—C5A—C6A | 118.7 (10) |
C21—C26—C25 | 119.3 (11) | C4A—C5A—H5A | 120.6 |
C21—C26—H26 | 120.4 | C5A—C4A—H4A | 118.6 |
C25—C26—H26 | 120.4 | C5A—C4A—C3A | 122.8 (11) |
N6—C27—H27A | 109.5 | C3A—C4A—H4A | 118.6 |
N6—C27—H27B | 109.5 | C4A—C3A—H3A | 121.1 |
N6—C27—H27C | 109.5 | C4A—C3A—C2A | 117.8 (10) |
H27A—C27—H27B | 109.5 | C2A—C3A—H3A | 121.1 |
H27A—C27—H27C | 109.5 | C1A—C2A—C3A | 118.2 (10) |
H27B—C27—H27C | 109.5 | C1A—C2A—H2A | 120.9 |
C29—C28—N6 | 121.2 (4) | C3A—C2A—H2A | 120.9 |
C33—C28—N6 | 120.9 (4) | ||
La1—N10—C61—C62 | 177.1 (3) | N8—C48—C49—C50 | −178.8 (4) |
La1—N10—C65—C64 | −175.9 (3) | N8—C48—C53—C52 | 178.7 (4) |
La1—N10—C65—C66 | 5.5 (4) | N9—P3—O3—La1 | −174.03 (17) |
La1—N11—C66—C65 | −8.6 (4) | N9—P3—N3—S3 | 150.9 (2) |
La1—N11—C66—C69 | 173.4 (3) | N9—P3—N8—C47 | 126.7 (4) |
La1—N11—C72—C71 | −174.2 (3) | N9—P3—N8—C48 | −51.4 (3) |
S1—C1—C2—C3 | −175.0 (18) | N9—C55—C56—C57 | 179.5 (4) |
S1—C1—C6—C5 | 175.2 (17) | N9—C55—C60—C59 | −179.9 (4) |
S1—C1A—C6A—C5A | 175.3 (19) | N10—C61—C62—C63 | −1.3 (7) |
S1—C1A—C2A—C3A | −177.0 (18) | N10—C65—C66—N11 | 2.1 (5) |
S2—C21—C22—C23 | −179.3 (10) | N10—C65—C66—C69 | −179.9 (3) |
S2—C21—C26—C25 | 179.4 (9) | N11—C66—C69—C68 | 179.1 (4) |
S2—C21A—C26A—C25A | −179.8 (14) | N11—C66—C69—C70 | 0.9 (6) |
S2—C21A—C22A—C23A | 179.7 (13) | C1—S1—O5—La1 | −101.7 (10) |
S3—C41—C46—C45 | −178.4 (2) | C1—S1—N1—P1 | 68.0 (8) |
S3—C41—C42—C43 | 178.3 (2) | C1—C2—C3—C4 | 0.0 |
P1—N4—C8—C9 | −0.3 (6) | C2—C1—C6—C5 | 0.0 |
P1—N4—C8—C13 | 177.4 (3) | C2—C3—C4—C5 | 0.0 |
P1—N5—C15—C20 | 13.4 (9) | C3—C4—C5—C6 | 0.0 |
P1—N5—C15—C16 | −168.9 (6) | C4—C5—C6—C1 | 0.0 |
P1—N5—C15A—C20A | 32.4 (12) | C6—C1—C2—C3 | 0.0 |
P1—N5—C15A—C16A | −147.3 (8) | C7—N4—C8—C9 | 179.4 (4) |
P2—N6—C28—C29 | −126.1 (4) | C7—N4—C8—C13 | −2.9 (6) |
P2—N6—C28—C33 | 51.6 (6) | C8—C9—C10—C11 | −0.7 (9) |
P2—N7—C35—C36 | 113.6 (4) | C9—C8—C13—C12 | 0.4 (8) |
P2—N7—C35—C40 | −66.0 (5) | C9—C10—C11—C12 | −0.3 (11) |
P3—N8—C48—C49 | 136.6 (4) | C10—C11—C12—C13 | 1.4 (12) |
P3—N8—C48—C53 | −44.2 (5) | C11—C12—C13—C8 | −1.5 (10) |
P3—N9—C55—C56 | 110.1 (4) | C13—C8—C9—C10 | 0.6 (8) |
P3—N9—C55—C60 | −71.8 (4) | C14—N5—C15—C20 | −162.4 (6) |
O1—P1—N1—S1 | 34.3 (3) | C14—N5—C15—C16 | 15.2 (11) |
O1—P1—N4—C7 | 128.0 (3) | C14—N5—C15A—C20A | −149.0 (7) |
O1—P1—N4—C8 | −52.3 (4) | C14—N5—C15A—C16A | 31.3 (13) |
O1—P1—N5—C14 | −14.2 (4) | C15—C20—C19—C18 | 0.0 |
O1—P1—N5—C15 | 170.0 (7) | C20—C15—C16—C17 | 0.0 |
O1—P1—N5—C15A | 164.4 (9) | C20—C19—C18—C17 | 0.0 |
O2—P2—N2—S2 | −5.2 (5) | C19—C18—C17—C16 | 0.0 |
O2—P2—N6—C27 | 121.4 (3) | C18—C17—C16—C15 | 0.0 |
O2—P2—N6—C28 | −72.4 (3) | C16—C15—C20—C19 | 0.0 |
O2—P2—N7—C34 | 176.2 (3) | C21—S2—O7—La1 | −139.0 (5) |
O2—P2—N7—C35 | 4.2 (4) | C21—S2—N2—P2 | 125.8 (6) |
O3—P3—N3—S3 | 27.6 (3) | C21—C22—C23—C24 | 0.1 (3) |
O3—P3—N8—C47 | −114.3 (4) | C22—C21—C26—C25 | 0.0 (6) |
O3—P3—N8—C48 | 67.7 (3) | C22—C23—C24—C25 | −0.4 (6) |
O3—P3—N9—C54 | 178.8 (3) | C23—C24—C25—C26 | 0.4 (8) |
O3—P3—N9—C55 | 29.6 (3) | C24—C25—C26—C21 | −0.2 (8) |
O4—S1—O5—La1 | 140.4 (2) | C26—C21—C22—C23 | 0.0 (3) |
O4—S1—N1—P1 | −174.3 (2) | C27—N6—C28—C29 | 40.8 (6) |
O4—S1—C1—C2 | −67.9 (11) | C27—N6—C28—C33 | −141.4 (5) |
O4—S1—C1—C6 | 116.9 (9) | C28—C29—C30—C31 | −0.3 (11) |
O4—S1—C1A—C6A | 117.5 (13) | C29—C28—C33—C32 | 1.6 (8) |
O4—S1—C1A—C2A | −63.3 (12) | C29—C30—C31—C32 | 1.4 (11) |
O5—S1—N1—P1 | −46.1 (3) | C30—C31—C32—C33 | −1.0 (10) |
O5—S1—C1—C2 | 170.6 (8) | C31—C32—C33—C28 | −0.5 (9) |
O5—S1—C1—C6 | −4.6 (12) | C33—C28—C29—C30 | −1.1 (8) |
O5—S1—C1A—C6A | −5.3 (17) | C34—N7—C35—C36 | −58.5 (6) |
O5—S1—C1A—C2A | 173.9 (9) | C34—N7—C35—C40 | 121.8 (5) |
O6—S2—O7—La1 | 111.0 (3) | C35—C36—C37—C38 | 0.3 (10) |
O6—S2—N2—P2 | −123.1 (4) | C36—C35—C40—C39 | −0.2 (7) |
O6—S2—C21—C22 | −142.0 (6) | C36—C37—C38—C39 | 0.6 (10) |
O6—S2—C21—C26 | 38.7 (7) | C37—C38—C39—C40 | −1.4 (10) |
O6—S2—C21A—C26A | 36.0 (11) | C38—C39—C40—C35 | 1.2 (8) |
O6—S2—C21A—C22A | −143.9 (7) | C40—C35—C36—C37 | −0.5 (8) |
O7—S2—N2—P2 | 6.5 (5) | C41—S3—O9—La1 | 66.7 (2) |
O7—S2—C21—C22 | 99.8 (7) | C41—S3—N3—P3 | −100.0 (2) |
O7—S2—C21—C26 | −79.6 (7) | C41—C46—C45—C44 | 0.0 |
O7—S2—C21A—C26A | −86.3 (10) | C46—C41—C42—C43 | 0.0 |
O7—S2—C21A—C22A | 93.9 (8) | C46—C45—C44—C43 | 0.0 |
O8—S3—O9—La1 | −177.3 (2) | C45—C44—C43—C42 | 0.0 |
O8—S3—N3—P3 | 143.7 (2) | C44—C43—C42—C41 | 0.0 |
O8—S3—C41—C46 | −42.6 (2) | C42—C41—C46—C45 | 0.0 |
O8—S3—C41—C42 | 139.03 (19) | C47—N8—C48—C49 | −41.5 (6) |
O9—S3—N3—P3 | 15.2 (3) | C47—N8—C48—C53 | 137.7 (5) |
O9—S3—C41—C46 | 77.96 (18) | C48—C49—C50—C51 | −1.3 (9) |
O9—S3—C41—C42 | −100.41 (19) | C49—C48—C53—C52 | −2.0 (7) |
N1—S1—O5—La1 | 14.1 (3) | C49—C50—C51—C52 | 0.7 (9) |
N1—S1—C1—C2 | 50.8 (12) | C50—C51—C52—C53 | −0.8 (9) |
N1—S1—C1—C6 | −124.3 (9) | C51—C52—C53—C48 | 1.5 (8) |
N1—S1—C1A—C6A | −125.4 (13) | C53—C48—C49—C50 | 1.9 (7) |
N1—S1—C1A—C2A | 53.8 (12) | C54—N9—C55—C56 | −39.3 (5) |
N1—P1—O1—La1 | 16.2 (3) | C54—N9—C55—C60 | 138.9 (4) |
N1—P1—N4—C7 | 2.5 (4) | C55—C56—C57—C58 | 0.2 (9) |
N1—P1—N4—C8 | −177.8 (3) | C56—C55—C60—C59 | −1.7 (7) |
N1—P1—N5—C14 | 112.8 (3) | C56—C57—C58—C59 | −1.4 (10) |
N1—P1—N5—C15 | −63.0 (7) | C57—C58—C59—C60 | 1.0 (10) |
N1—P1—N5—C15A | −68.6 (9) | C58—C59—C60—C55 | 0.6 (8) |
N2—S2—O7—La1 | −18.5 (4) | C60—C55—C56—C57 | 1.3 (7) |
N2—S2—C21—C22 | −23.1 (8) | C61—N10—C65—C64 | 0.2 (5) |
N2—S2—C21—C26 | 157.5 (5) | C61—N10—C65—C66 | −178.3 (3) |
N2—S2—C21A—C26A | 154.9 (8) | C61—C62—C63—C64 | 0.5 (7) |
N2—S2—C21A—C22A | −24.9 (8) | C62—C63—C64—C65 | 0.6 (7) |
N2—P2—O2—La1 | 14.7 (3) | C62—C63—C64—C67 | −179.4 (4) |
N2—P2—N6—C27 | −6.2 (4) | C63—C64—C65—N10 | −1.0 (6) |
N2—P2—N6—C28 | 160.0 (3) | C63—C64—C65—C66 | 177.6 (4) |
N2—P2—N7—C34 | −56.6 (4) | C63—C64—C67—C68 | −179.4 (4) |
N2—P2—N7—C35 | 131.4 (4) | C64—C65—C66—N11 | −176.5 (3) |
N3—S3—O9—La1 | −49.8 (3) | C64—C65—C66—C69 | 1.5 (5) |
N3—S3—C41—C46 | −162.13 (17) | C64—C67—C68—C69 | 2.1 (7) |
N3—S3—C41—C42 | 19.5 (2) | C65—N10—C61—C62 | 0.9 (6) |
N3—P3—O3—La1 | −51.9 (2) | C65—C64—C67—C68 | 0.7 (7) |
N3—P3—N8—C47 | 13.8 (4) | C65—C66—C69—C68 | 1.1 (5) |
N3—P3—N8—C48 | −164.2 (3) | C65—C66—C69—C70 | −177.1 (4) |
N3—P3—N9—C54 | 52.0 (3) | C66—N11—C72—C71 | 0.1 (6) |
N3—P3—N9—C55 | −97.3 (3) | C66—C69—C70—C71 | 0.1 (6) |
N4—P1—O1—La1 | −102.5 (2) | C67—C64—C65—N10 | 179.0 (4) |
N4—P1—N1—S1 | 158.3 (2) | C67—C64—C65—C66 | −2.5 (6) |
N4—P1—N5—C14 | −134.8 (3) | C67—C68—C69—C66 | −3.0 (7) |
N4—P1—N5—C15 | 49.4 (7) | C67—C68—C69—C70 | 175.1 (4) |
N4—P1—N5—C15A | 43.8 (9) | C68—C69—C70—C71 | −178.1 (4) |
N4—C8—C9—C10 | 178.4 (5) | C69—C70—C71—C72 | −0.9 (7) |
N4—C8—C13—C12 | −177.4 (5) | C70—C71—C72—N11 | 0.8 (7) |
N5—P1—O1—La1 | 141.5 (2) | C72—N11—C66—C65 | 177.0 (3) |
N5—P1—N1—S1 | −87.6 (3) | C72—N11—C66—C69 | −1.0 (5) |
N5—P1—N4—C7 | −116.1 (3) | C21A—S2—O7—La1 | −129.7 (7) |
N5—P1—N4—C8 | 63.6 (3) | C21A—S2—N2—P2 | 121.1 (7) |
N5—C15—C20—C19 | 177.6 (10) | C21A—C26A—C25A—C24A | −0.1 (3) |
N5—C15—C16—C17 | −177.6 (10) | C26A—C21A—C22A—C23A | −0.1 (6) |
N5—C15A—C20A—C19A | −179.7 (14) | C26A—C25A—C24A—C23A | 0.2 (7) |
N5—C15A—C16A—C17A | 179.8 (12) | C25A—C24A—C23A—C22A | −0.3 (9) |
N6—P2—O2—La1 | −106.2 (3) | C24A—C23A—C22A—C21A | 0.3 (8) |
N6—P2—N2—S2 | 120.4 (4) | C22A—C21A—C26A—C25A | 0.0 (3) |
N6—P2—N7—C34 | 54.7 (4) | C15A—C20A—C19A—C18A | 0.0 |
N6—P2—N7—C35 | −117.3 (4) | C20A—C15A—C16A—C17A | 0.0 |
N6—C28—C29—C30 | 176.7 (5) | C20A—C19A—C18A—C17A | 0.0 |
N6—C28—C33—C32 | −176.3 (5) | C19A—C18A—C17A—C16A | 0.0 |
N7—P2—O2—La1 | 137.1 (2) | C18A—C17A—C16A—C15A | 0.0 |
N7—P2—N2—S2 | −127.5 (4) | C16A—C15A—C20A—C19A | 0.0 |
N7—P2—N6—C27 | −120.4 (4) | C1A—S1—O5—La1 | −100.8 (10) |
N7—P2—N6—C28 | 45.8 (3) | C1A—S1—N1—P1 | 70.5 (8) |
N7—C35—C36—C37 | 179.8 (5) | C1A—C6A—C5A—C4A | 1.2 (16) |
N7—C35—C40—C39 | 179.5 (4) | C6A—C1A—C2A—C3A | 2.2 (15) |
N8—P3—O3—La1 | 70.8 (2) | C6A—C5A—C4A—C3A | 3.0 (18) |
N8—P3—N3—S3 | −99.3 (3) | C5A—C4A—C3A—C2A | −4.5 (18) |
N8—P3—N9—C54 | −59.5 (3) | C4A—C3A—C2A—C1A | 1.8 (16) |
N8—P3—N9—C55 | 151.3 (3) | C2A—C1A—C6A—C5A | −3.8 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C70—H70···O4i | 0.93 | 2.67 | 3.444 (6) | 139 |
C56—H56···O4ii | 0.93 | 2.71 | 3.448 (5) | 136 |
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, z+1/2. |
Acknowledgements
The authors acknowledge Svitlana V. Shishkina, head of the Department of X-ray Diffraction Study and Quantum Chemistry, STC `Institute for Single Crystals' for the data collection.
References
Adams, L. A., Cox, R. J., Gibson, J. S., Mayo-Martín, M. B., Walter, M. & Whittingham, W. (2002). Chem. Commun. pp. 2004–2005. Web of Science CrossRef Google Scholar
Agilent (2016). CrysAlis PRO. Agilent Technologies Inc., Yarnton, England. Google Scholar
Amirkhanov, V., Janczak, C., Macalik, L., Hanuza, J. & Legendziewicz, J. (1995). J. Appl. Spectrosc. 62, 613–624. CrossRef Google Scholar
Amirkhanov, O. V., Moroz, O. V., Znovjyak, K. O., Sliva, T. Y., Penkova, L. V., Yushchenko, T., Szyrwiel, L., Konovalova, I. S., Dyakonenko, V. V., Shishkin, O. V. & Amirkhanov, V. M. (2014). Eur. J. Inorg. Chem. 2014, 3720–3730. CSD CrossRef CAS Google Scholar
Beloso, I., Castro, J., García-Vázquez, J. A., Pérez-Lourido, P., Romero, J. & Sousa, A. (2003). Polyhedron, 22, 1099–1111. Web of Science CSD CrossRef CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gawryszewska, P., Moroz, O. V., Trush, V. A., Kulesza, D. & Amirkhanov, V. M. (2011). J. Photochem. Photobiol. Chem. 217, 1–9. CSD CrossRef CAS Google Scholar
Gholivand, K., Molaei, F., Oroujzadeh, N., Mobasseri, R. & Naderi-Manesh, H. (2014). Inorg. Chim. Acta, 423, 107–116. CSD CrossRef CAS Google Scholar
Gholivand, K., Oroujzadeh, N. & Rajabi, M. (2012). J. Iran. Chem. Soc. 9, 865–876. CSD CrossRef CAS Google Scholar
Grimes, K. D., Lu, Y.-J., Zhang, Y.-M., Luna, V. A., Hurdle, J. G., Carson, E. I., Qi, J., Sucheta Kudrimoti, S., Rock, C. O. & Lee, R. E. (2008). ChemMedChem, 12, 1936–1945. CrossRef Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jaroslav, K. & Swerdloff, F. (1985). US Patent 4 517 003. Google Scholar
Kariaka, N. S., Trush, V. A., Medviediev, V. V., Sliva, T. Y. & Amirkhanov, V. M. (2013). Acta Cryst. E69, m143. CSD CrossRef IUCr Journals Google Scholar
Kasprzycka, E., Trush, V. A., Amirkhanov, V. M., Jerzykiewicz, L., Malta, O. L., Legendziewicz, J. & Gawryszewska, P. (2016). Chem. Eur. J. 22, 1–14. Google Scholar
Kirsanov, A. & Shevchenko, V. (1954). Zh. Obshch. Khim. pp. 1980–1993. Google Scholar
Kishino, S. & Saito, S. (1979). US Patent 4 161 524. Google Scholar
Kovalchyk, T. V., Kudryavtseva, I. G., Sharykina, N. I. & Arzyaeva, E. A. (1991). Khim. Farm. Zh. 6, 63–64. Google Scholar
Kulesza, D., Sobczyk, M., Legendziewicz, J., Moroz, O. & Amirkhanov, V. (2010). Struct. Chem. 21, 425–438. CrossRef CAS Google Scholar
Litsis, O. O., Ovchynnikov, V. A., Scherbatskii, V. P., Nedilko, S. G., Sliva, T. Yu., Dyakonenko, V. V., Shishkin, O. V., Davydov, V. I., Gawryszewska, P. & Amirkhanov, V. M. (2015). Dalton Trans. 44, 15508–15522. Web of Science CSD CrossRef CAS PubMed Google Scholar
Litsis, O. O., Ovchynnikov, V. A., Sliva, T. Y., Konovalova, I. S. & Amirkhanov, V. M. (2010). Acta Cryst. E66, m426–m427. Web of Science CSD CrossRef IUCr Journals Google Scholar
Litsis, O. O., Shatrava, I. O., Amirkhanov, O. V., Ovchynnikov, V. A., Sliva, T. Yu., Shishkina, S. V., Dyakonenko, V. V., Shishkin, O. V. & Amirkhanov, V. M. (2016). Struct. Chem. 27, 341–355. CSD CrossRef CAS Google Scholar
Litsis, O. O., Sliva, T. Y., Amirkhanov, V. M., Kolomzarov, Y. V. & Minakova, I. E. (2017). Proc. Int. Conf. Adv. Optoelectronics and Lasers, CAOL., Article number 7851409, 151-153. Google Scholar
Morgalyuk, V. P., Safiulina, A. M., Tananaev, I. G., Goryunov, E. I., Goryunova, I. B., Molchanova, G. N., Baulina, T. V., Nifant'ev, E. E. & Myasoedov, B. F. (2005). Dokl. Chem. 403, 126–128. Web of Science CrossRef CAS Google Scholar
Moroz, O. V., Shishkina, S. V., Trush, V. A., Sliva, T. Y. & Amirkhanov, V. M. (2007). Acta Cryst. E63, m3175–m3176. Web of Science CSD CrossRef IUCr Journals Google Scholar
Moroz, O., Trush, V., Znovjyak, K., Konovalova, I., Omelchenko, I., Sliva, T., Shishkin, O. & Amirkhanov, V. (2012). J. Mol. Struct. 1017, 109–114. CSD CrossRef CAS Google Scholar
Oroujzadeh, N., Gholivand, K. & Jamalabadi, N. R. (2017). Polyhedron, 122, 29–38. CSD CrossRef CAS Google Scholar
Porai-Koshits, M. & Aslanov, L. (1972). Zh. Strukt. Khim. 13, 266–276. CAS Google Scholar
Rogachev, A., Minacheva, L., Sergienko, V., Malkerova, I., Alikhanyan, A., Stryapan, V. & Kuzmina, N. (2005). Polyhedron, 24, 723–729. CSD CrossRef CAS Google Scholar
Safiulina, A. M., Matveeva, A. G., Lizunov, A. V., Bodrin, G. V., Goryunov, E. I., Grigor'ev, M. S., Semenov, A. A., Brel, V. K. & Nifant'ev, E. E. (2015). Dokl. Chem. 460, 57–60. CSD CrossRef CAS Google Scholar
Shatrava, I., Gubina, K., Ovchynnikov, V., Dyakonenko, V. & Amirkhanov, V. (2016a). Acta Cryst. E72, 1683–1686. CSD CrossRef IUCr Journals Google Scholar
Shatrava, I., Ovchynnikov, V., Gubina, K., Shishkina, S., Shishkin, O. & Amirkhanov, V. (2016b). Struct. Chem. 27, 1413–1425. CSD CrossRef CAS Google Scholar
Shatrava, I. O., Sliva, T. Y., Ovchynnikov, V. A., Konovalova, I. S. & Amirkhanov, V. M. (2010). Acta Cryst. E66, m397–m398. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sokolnicki, J., Legendziewicz, J., Amirkhanov, W., Ovchinnikov, V., Macalik, L. & Hanuza, J. (1999). Spectrochim. Acta A, 55, 349–367. CrossRef Google Scholar
Spek, A. L. (2015). Acta Cryst. C71, 9–18. Web of Science CrossRef IUCr Journals Google Scholar
Xu, K. & Angell, C. A. (2000). Inorg. Chim. Acta, 298, 16–23. CrossRef CAS Google Scholar
Yizhak, R. V., Znovjyak, K. O., Ovchynnikov, V. A., Sliva, T. Y., Konovalova, I. S., Medviediev, V. V., Shishkin, O. V. & Amirkhanov, V. M. (2013). Polyhedron, 62, 293–299. CSD CrossRef CAS Google Scholar
Zefirov, N. S., Palyulin, V. A. & Dashevskaya, E. E. (1990). J. Phys. Org. Chem. 3, 147–158. CrossRef CAS Web of Science Google Scholar
Znovjyak, K. O., Ovchynnikov, V. A., Sliva, T. Y., Shishkina, S. V. & Amirkhanov, V. M. (2009). Acta Cryst. E65, o2812. Web of Science CSD CrossRef IUCr Journals Google Scholar
Znovjyak, K. O., Seredyuk, M., Kusz, J., Nowak, M., Moroz, O. V., Sliva, T. Yu. & Amirkhanov, V. M. (2015). J. Mol. Struct. 1100, 145–149. CSD CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.