research communications
n-butylammonium counter-ions
of a host–guest complex of the tris-urea receptor, 3-(4-nitrophenyl)-1,1-bis{2-[3-(4-nitrophenyl)ureido]ethyl}urea, that encapsulates hydrogen-bonded chains of dihydrogen phosphate anions with separate tetra-aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
*Correspondence e-mail: chuang@scu.edu.cn
The title compound, C25H25N9O9·C16H36N+·H2PO4− (I) or (C25H25N9O9)·(n-Bu4N+)·(H2PO4−) (systematic name: 3-(4-nitrophenyl)-1,1-bis{2-[3-(4-nitrophenyl)ureido]ethyl}urea tetrabutylammonium dihydrogen phosphate), comprises a tris-urea receptor (R), a dihydrogen phosphate anion and a tetra-n-butylammonium cation. It crystallizes with two independent formula units in the The conformations of the two tris-urea receptors are stabilized by N—H⋯O and C—H⋯O intramolecular hydrogen bonds. Each dihydrogen phosphate anion has two O—H⋯O intermolecular hydrogen-bonding interactions with the other dihydrogen phosphate anion. Inversion-related di-anion units are linked by further O—H⋯O hydrogen bonds, forming a chain propagating along the a-axis direction. Each dihydrogen phosphate anion makes a total of four N—H⋯O(H2PO4−) hydrogen bonds with two ureido subunits from two different tris-urea receptors, hence each tris-urea receptor provides the two ureido subunits for the encapsulation of the H2PO4− hydrogen-bonded chain. There are numerous intermolecular C—H⋯O hydrogen bonds present involving both receptor molecules and the tetra-n-butylammonium cations, so forming a supramolecular three-dimensional structure. One of the butyl groups and one of the nitro groups are disordered over two positions of equal occupancy.
Keywords: crystal structure; tris-urea; tetra-n-butylammonium; dihydrogen phosphate; anionic polymer; hydrogen bonding; supramolecular three-dimensional structure.
CCDC reference: 1893140
1. Chemical context
Anions play an important role in many chemical, catalysis, environmental and biological systems (Sessler et al., 2006; Vickers & Beer, 2007; Beer & Gale, 2001). The use of urea-based receptors as hydrogen-bond donors in anion recognition has attracted much attention (Xu et al., 2017; Amendola et al., 2006; Hoque & Das, 2017; Bregović et al., 2015; Li et al., 2010). In particular, considerable research efforts have been devoted to the designation of receptors containing a ureido subunit (which selectively recognizes fluoride ions), such as 1,3-bis(4-nitrophenyl) urea (Boiocchi et al., 2004), or a urea subunit equipped with two naphthalenimide moieties (Esteban-Gómez et al., 2005), and thiourea or urea-based indole conjugated ligands (Bose & Ghosh, 2010). Recently, tris(2-aminoethyl)amine (tren)-based tripodal urea or thiourea receptors for the recognition and separation of anions have been investigated (Arunachalam & Ghosh, 2011; Custelcean, 2013; Dey et al., 2016; Hay et al., 2005). However, tris-urea receptors have been rarely studied to date. In our ongoing research on nitrogen-rich organic ligands (Wang et al., 2015) and the design and synthesis of ureido receptors (Huang et al., 2017), we report herein the synthesis of the title tris-urea receptor, 3-(4-nitrophenyl)-1,1-bis{2-[3-(4-nitrophenyl)ureido]ethyl}urea (R), based on p-nitrophenyl substituents, and the of its complex with tetra-n-butylammonium dihydrogen phosphate. Interestingly, a one-dimensional hydrogen-bonded polymeric structure is formed via hydrogen bonds between dihydrogen phosphate anions, and this anionic polymer is surrounded by and linked to the tris-urea receptors through ureido N—H⋯O hydrogen bonds.
2. Structural commentary
The title compound crystallizes with two independent formula units in the R1 and R2) and the dihydrogen phosphate anions (P1 and P2) are illustrated in Fig. 1. In each receptor an intramolecular N—H⋯O hydrogen bond is present (N8—H8N⋯O7 in R1 and N17—H17N⋯O16 in R2), each forming an S(9) ring motif,. Four intramolecular C—H⋯O hydrogen bonds are also present in receptor R1 and three in R2 (Fig. 1 and Table 1). Both receptors display a cis orientation of the urea subunits (N2/N3 and N5/N6 in R1, and N11/N12 and N14/N15 in R2). The urea subunits N5/N6 in R1 and N11/N12 in R2 are orientated towards the dihydrogen phosphate ions (P1 and P2) forming a 2:2 adduct via N—H⋯O hydrogen bonds with anion P1 and enclosing R22(8) ring motifs (Table 1 and Fig. 1). Both NH functions of each urea subunit are trans to the C=O group across the respective C—N bond. Anions P1 and P2 interact with each other via two O—H⋯O hydrogen bonds (O20—H20O⋯O24 and O23—H23O⋯O22), enclosing an R22(8) ring motif (Fig. 1 and Table 1). The dihedral angle between the urea plane [N—C(=O)—N] and the benzene ring to which it is attached vary from 6.66 (14) to 18.96 (14)° in R1 and from 6.87 (14) to 13.82 (14)° in R2. The dihedral angle between the nitro group and the benzene ring to which it is attached also vary, from 7.1 (3) to 13.4 (4)° in R1 and from 8.3 (4) to 16.7 (7)° in R2.
The molecular structure of the two tris-urea receptors (3. Supramolecular features
In the crystal, the two H2PO4− anions (P1 and P2), that are linked by O—H⋯O hydrogen bonds O20—H20O⋯O24 and O23—H23O⋯O22, are further linked to inversion-related anions via hydrogen bonds O21—H21O⋯O19i and O25—H25O⋯O26ii (Table 1). This results in the formation of a polymer chain propagating along the a-axis direction (Fig. 2). The receptor molecules are linked to this chain via hydrogen bonds N5—H5N⋯O21, N6—H6N⋯O22, N11—H11N⋯O19, and N12—H12N⋯O22 (Fig. 1), and by hydrogen bonds N2—H2N⋯O26i, N3—H3N⋯O24i, N14—H14N⋯O25ii and N15—H15N⋯O24ii (Table 1). Finally, there are numerous intermolecular C—H⋯O hydrogen bonds present involving both receptor molecules and the tetra-n-butylammonium cations, so forming a supramolecular three-dimensional structure (Fig. 3 and Table 1).
4. Database survey
The R, with or without para-substitution of a nitro group, has not previously been reported. A search of the Cambridge Structural Database (Version 5.40, November 2018; Groom et al., 2016) for tetra-n-butylammonium dihydrogen phosphate yielded four hits, essentially concerning the tris-urea receptor based on tris(2-aminoethyl)amine (tren). One of these compounds, tetra-n-butylammonium tris(2-(N-perfluorophenylureaylato)ethyl)amine dihydrogen phosphate dimethylformamide monosolvate, encapsulates a dimer of H2PO4− anions forming a pseudo-dimeric cage via sixteen hydrogen bonds and two weak anion⋯π interactions (CSD refcode CITYOU; Lakshminarayanan et al., 2007). Another example is, N,N′,N′′-[nitrilotris(ethane-2,1-diyl)]tris(N′-phenylurea) tetra-n-butylammonium dihydrogen phosphate (YICHUQ; Manna & Das, 2018). Here too, a dimer of H2PO4− anions is encapsulated by the receptor.
of the receptorChiral anion receptors with two enantiomeric forms R,R and S,S based on a 1,2-cyclohexane moiety appended by two p-nitrophenylurea subunits have been reported. One such compound is bis(tetra-n-butylammonium) bis(dihydrogen phosphate) (R,R)-1-(4-nitrophenyl)-3-{2-[3-(4-nitrophenyl)ureido]cyclohexyl}urea acetonitrile monosolvate (DASNUH; Amendola et al., 2005). The nature of the R,R-enantiomer⋯H2PO4− interactions is characterized by infinite dihydrogen phosphate chains along the a-axis direction, as observed in the of the title complex. Specifically, each dihydrogen phosphate ion interacts with two adjacent H2PO4− ions and with only one R,R-enantiomer via two hydrogen bonds. The hydrogen bonds in this enantiomeric complex are similar to those in the title complex, with the H⋯acceptor distance between the urea N—H group and the dihydrogen phosphate oxygen atom varying between ca 1.98 and 2.19 Å in DASNUH compared to a range of 1.96 (2)–2.21 (2) Å in the title compound. The O—H⋯O hydrogen bonds involving the H2PO4− anions are also very similar: 1.62 (3) and 1.63 (4) Å in DASNUH, while they vary from 1.59 (2) to 1.66 (2) Å in the title complex.
5. Synthesis and crystallization
Synthesis of 3-(4-nitrophenyl)-1,1-bis{2-[3-(4-nitrophenyl)ureido]ethyl}urea (R): In a 250 ml round-bottom flask, diethylenetriamine (0.32 ml, 2.97 mmol) dissolved in 100 ml of dry CH2Cl2 was added dropwise under vigorous stirring to a solution of 20 ml of dry CH2Cl2 containing p-nitrobenzene isocyanate (1.64 g, 9.98 mmol). Subsequently, the reaction mixture was allowed to reflux for 24 h. A yellowish solid was collected by filtration and washed using sequentially CH2Cl2 (3 × 70 ml), a solvent mixture (CH2Cl2/THF = 4:1, 3 × 70 ml) and diethyl ether (3 × 70 ml). The solid was then dried in vacuo overnight to afford the receptor R as a light-brown powder (yield: 1.52 g; 85.6%; m.p. 512.3–513.8 K). FT–IR (KBr, cm−1): 3339, 1679, 1606, 1559, 1501, 1330. 1H NMR (400 MHz, DMSO-d6) in ppm: δ = 9.42 (s, 2H), 9.23 (s, 1H), 8.10 (t, J = 9.9 Hz, 6H), 7.76 (d, J = 8.9 Hz, 2H), 7.59 (d, J = 8.9 Hz, 4H), 6.60 (t, J = 5.8 Hz, 2H), 3.51 (t, J = 6.5 Hz, 4H). 13C NMR (100 MHz, DMSO-d6) in ppm: δ = 154.99, 154.67, 147.34, 146.94, 140.72, 140.48, 125.09, 124.70, 118.13, 116.95, 46.63, 40.15–38.89, 38.19. HRMS (ESI+): calculated for C25H25N9O9Na [M + Na]+ 618.1673 found 618.1678.
Synthesis of the title complex (I): Tetra-n-butylammonium dihydrogen phosphate (1.68 mmol) was added to 5 ml of a DMF solution of R (0.168 mmol) and the mixture was stirred for 2 h. After filtration the solution was left to evaporate slowly and yielded colourless prismatic crystals of the title complex within three weeks.
6. Refinement
Crystal data, data collection and structure . H atoms bonded to O and N were located in a difference-Fourier map and refined with distance restraints: O—H = 0.93 and N—H = 0.90 Å, with Uiso(H) = 1.5Ueq(O) and 1.2Ueq(N). The C-bound H atoms were positioned geometrically and refined using a riding model: C—H = 0.95–0.99 Å, with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms.
details are summarized in Table 2
|
One of the butyl moieties (C79—C80—C81—C82) is disordered over two positions with equal occupancies. The C—C distances were refined with the restraint of 1.515 (4) Å. The displacement parameters of the C79A/C79B, C80A/C80B, C81A/C81B, and C82A/C82B atoms of the disordered fragment were restrained to be similar (Sheldrick, 2015b). Also, one of the nitro groups (O11—N10—O10) was disordered over two positions with equal occupancies. The N—O distances were refined with the restraint of 1.230 (4) Å. The displacement parameters of the O10A/O11A and O10B/O11B atoms of the disordered fragment were restrained to be similar (Sheldrick, 2015b).
Supporting information
CCDC reference: 1893140
https://doi.org/10.1107/S2056989019001336/kq2020sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019001336/kq2020Isup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019001336/kq2020Isup3.cml
Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).C25H25N9O9·C16H36N+·H2PO4− | Z = 4 |
Mr = 934.98 | F(000) = 1992 |
Triclinic, P1 | Dx = 1.320 Mg m−3 |
a = 15.2043 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 17.4555 (5) Å | Cell parameters from 22142 reflections |
c = 18.1232 (4) Å | θ = 4.2–72.6° |
α = 83.797 (2)° | µ = 1.13 mm−1 |
β = 79.818 (2)° | T = 179 K |
γ = 89.191 (2)° | Prism, colourless |
V = 4706.3 (2) Å3 | 0.40 × 0.40 × 0.10 mm |
Agilent New Gemini, Dual, Cu at zero, EosS2 diffractometer | 18359 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 15323 reflections with I > 2σ(I) |
Detector resolution: 15.9595 pixels mm-1 | Rint = 0.040 |
ω scans | θmax = 72.7°, θmin = 4.5° |
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2014) | h = −12→18 |
Tmin = 0.660, Tmax = 0.880 | k = −21→21 |
50539 measured reflections | l = −21→22 |
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)] = 0.065 | Hydrogen site location: mixed |
wR(F2) = 0.160 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.06P)2 + 6P] where P = (Fo2 + 2Fc2)/3 |
18359 reflections | (Δ/σ)max = 0.001 |
1237 parameters | Δρmax = 0.96 e Å−3 |
26 restraints | Δρmin = −0.85 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) | |
O1 | −0.30049 (14) | 0.81991 (14) | 0.21069 (13) | 0.0558 (5) | |
O2 | −0.24548 (15) | 0.71532 (13) | 0.16732 (13) | 0.0563 (5) | |
O3 | 0.14525 (13) | 0.70324 (12) | 0.30808 (13) | 0.0499 (5) | |
O4 | 0.41981 (13) | 0.66636 (13) | 0.25280 (13) | 0.0541 (6) | |
O5 | 0.73924 (19) | 0.44154 (18) | 0.07252 (17) | 0.0814 (8) | |
O6 | 0.81027 (19) | 0.41318 (15) | 0.16481 (15) | 0.0741 (8) | |
O7 | 0.67230 (13) | 0.71270 (11) | 0.39515 (11) | 0.0431 (4) | |
O8 | 1.11079 (14) | 0.66722 (14) | 0.52832 (14) | 0.0590 (6) | |
O9 | 1.07222 (16) | 0.57359 (15) | 0.47126 (13) | 0.0639 (6) | |
N1 | −0.24296 (16) | 0.76864 (15) | 0.20575 (14) | 0.0456 (6) | |
N2 | 0.05445 (14) | 0.80478 (12) | 0.34212 (12) | 0.0349 (5) | |
H2N | 0.053 (2) | 0.8466 (10) | 0.3671 (15) | 0.042* | |
N3 | 0.18575 (14) | 0.78414 (13) | 0.38582 (13) | 0.0380 (5) | |
H3N | 0.173 (2) | 0.8242 (12) | 0.4129 (15) | 0.046* | |
N4 | 0.43055 (15) | 0.74282 (14) | 0.34333 (14) | 0.0433 (5) | |
N5 | 0.61267 (16) | 0.82824 (14) | 0.42129 (14) | 0.0437 (5) | |
H5N | 0.623 (2) | 0.8733 (10) | 0.4382 (18) | 0.052* | |
N6 | 0.73250 (14) | 0.78432 (13) | 0.47369 (13) | 0.0365 (5) | |
H6N | 0.722 (2) | 0.8271 (10) | 0.4972 (15) | 0.044* | |
N7 | 1.05762 (17) | 0.63522 (16) | 0.49814 (14) | 0.0479 (6) | |
N8 | 0.54553 (15) | 0.65876 (14) | 0.30550 (14) | 0.0413 (5) | |
H8N | 0.5769 (18) | 0.6786 (17) | 0.3366 (14) | 0.050* | |
N9 | 0.75357 (19) | 0.44901 (16) | 0.13596 (17) | 0.0575 (7) | |
C1 | 0.69928 (19) | 0.50461 (16) | 0.17902 (17) | 0.0454 (7) | |
C2 | 0.6241 (2) | 0.5329 (2) | 0.1551 (2) | 0.0576 (8) | |
H2 | 0.6087 | 0.5183 | 0.1100 | 0.069* | |
C3 | 0.5703 (2) | 0.5832 (2) | 0.19681 (19) | 0.0545 (8) | |
H3 | 0.5170 | 0.6023 | 0.1810 | 0.065* | |
C4 | 0.59415 (18) | 0.60564 (15) | 0.26166 (16) | 0.0399 (6) | |
C5 | 0.67121 (19) | 0.57639 (17) | 0.28422 (17) | 0.0449 (6) | |
H5 | 0.6879 | 0.5916 | 0.3286 | 0.054* | |
C6 | 0.7244 (2) | 0.52534 (17) | 0.24328 (18) | 0.0476 (7) | |
H6 | 0.7771 | 0.5051 | 0.2592 | 0.057* | |
C7 | 0.46280 (17) | 0.68813 (16) | 0.29743 (16) | 0.0411 (6) | |
C8 | 0.34579 (17) | 0.77955 (16) | 0.33457 (16) | 0.0398 (6) | |
H8A | 0.3335 | 0.7736 | 0.2836 | 0.048* | |
H8B | 0.3503 | 0.8353 | 0.3389 | 0.048* | |
C9 | 0.26874 (17) | 0.74518 (16) | 0.39328 (16) | 0.0392 (6) | |
H9A | 0.2624 | 0.6899 | 0.3876 | 0.047* | |
H9B | 0.2819 | 0.7492 | 0.4443 | 0.047* | |
C10 | 0.13050 (17) | 0.75938 (15) | 0.34299 (15) | 0.0359 (5) | |
C11 | −0.01842 (16) | 0.79138 (15) | 0.30923 (14) | 0.0342 (5) | |
C12 | −0.02853 (18) | 0.72636 (16) | 0.27224 (16) | 0.0400 (6) | |
H12 | 0.0161 | 0.6877 | 0.2694 | 0.048* | |
C13 | −0.10298 (18) | 0.71844 (16) | 0.24008 (16) | 0.0419 (6) | |
H13 | −0.1096 | 0.6745 | 0.2149 | 0.050* | |
C14 | −0.16814 (17) | 0.77457 (16) | 0.24457 (15) | 0.0382 (6) | |
C15 | −0.16132 (18) | 0.83798 (16) | 0.28272 (16) | 0.0412 (6) | |
H15 | −0.2074 | 0.8754 | 0.2868 | 0.049* | |
C16 | −0.08709 (18) | 0.84628 (16) | 0.31461 (15) | 0.0394 (6) | |
H16 | −0.0820 | 0.8899 | 0.3408 | 0.047* | |
C17 | 0.47607 (18) | 0.76651 (17) | 0.40141 (16) | 0.0424 (6) | |
H17A | 0.5019 | 0.7206 | 0.4266 | 0.051* | |
H17B | 0.4321 | 0.7894 | 0.4399 | 0.051* | |
C18 | 0.55022 (18) | 0.82489 (17) | 0.36954 (16) | 0.0421 (6) | |
H18A | 0.5826 | 0.8104 | 0.3207 | 0.051* | |
H18B | 0.5238 | 0.8764 | 0.3603 | 0.051* | |
C19 | 0.67255 (17) | 0.77080 (15) | 0.42772 (15) | 0.0376 (6) | |
C20 | 0.81048 (17) | 0.74344 (15) | 0.48085 (14) | 0.0342 (5) | |
C21 | 0.82524 (19) | 0.66802 (16) | 0.46242 (16) | 0.0424 (6) | |
H21 | 0.7800 | 0.6409 | 0.4458 | 0.051* | |
C22 | 0.9062 (2) | 0.63326 (16) | 0.46862 (16) | 0.0442 (6) | |
H22 | 0.9170 | 0.5824 | 0.4553 | 0.053* | |
C23 | 0.97117 (18) | 0.67192 (16) | 0.49395 (14) | 0.0392 (6) | |
C24 | 0.95747 (18) | 0.74567 (16) | 0.51434 (14) | 0.0386 (6) | |
H24 | 1.0023 | 0.7714 | 0.5328 | 0.046* | |
C25 | 0.87735 (17) | 0.78116 (15) | 0.50729 (14) | 0.0358 (5) | |
H25 | 0.8674 | 0.8321 | 0.5206 | 0.043* | |
O10A | 0.0479 (3) | 0.8828 (3) | 0.8867 (3) | 0.0689 (14) | 0.5 |
O11A | 0.0502 (7) | 0.9794 (7) | 0.8022 (6) | 0.0689 (14) | 0.5 |
O10B | 0.0574 (3) | 0.9139 (3) | 0.90363 (18) | 0.0515 (10) | 0.5 |
O11B | 0.0563 (6) | 0.9790 (6) | 0.7960 (4) | 0.0515 (10) | 0.5 |
O12 | 0.49661 (14) | 0.78528 (13) | 0.82348 (11) | 0.0516 (5) | |
O13 | 0.75401 (12) | 0.75789 (11) | 0.88681 (10) | 0.0390 (4) | |
O14 | 0.94784 (18) | 0.54938 (14) | 1.15633 (12) | 0.0654 (7) | |
O15 | 1.07221 (14) | 0.52318 (12) | 1.08658 (12) | 0.0483 (5) | |
O16 | 1.08082 (12) | 0.76689 (11) | 0.73581 (10) | 0.0381 (4) | |
O17 | 1.50576 (19) | 0.61542 (18) | 0.70411 (17) | 0.0847 (9) | |
O18 | 1.56917 (14) | 0.68624 (14) | 0.60480 (15) | 0.0620 (6) | |
N10 | 0.08998 (16) | 0.93022 (17) | 0.83676 (13) | 0.0572 (7) | |
N11 | 0.44803 (14) | 0.86420 (13) | 0.72873 (12) | 0.0362 (5) | |
H11N | 0.4688 (19) | 0.8905 (15) | 0.6837 (8) | 0.043* | |
N12 | 0.58895 (15) | 0.81643 (13) | 0.71123 (13) | 0.0392 (5) | |
H12N | 0.599 (2) | 0.8456 (15) | 0.6666 (9) | 0.047* | |
N13 | 0.81504 (13) | 0.79785 (12) | 0.76640 (11) | 0.0336 (4) | |
N14 | 1.03777 (14) | 0.86411 (13) | 0.65735 (12) | 0.0361 (5) | |
H14N | 1.0554 (19) | 0.9028 (12) | 0.6211 (12) | 0.043* | |
N15 | 1.17809 (14) | 0.81480 (12) | 0.62862 (12) | 0.0341 (4) | |
H15N | 1.181 (2) | 0.8486 (13) | 0.5873 (10) | 0.041* | |
N16 | 1.50353 (18) | 0.66548 (16) | 0.65167 (16) | 0.0543 (6) | |
N17 | 0.90190 (13) | 0.73247 (13) | 0.84589 (12) | 0.0339 (4) | |
H17N | 0.9496 (12) | 0.7446 (17) | 0.8097 (12) | 0.041* | |
N18 | 0.99925 (17) | 0.55484 (13) | 1.09594 (13) | 0.0407 (5) | |
C26 | 1.41791 (18) | 0.70288 (16) | 0.64585 (17) | 0.0429 (6) | |
C27 | 1.41575 (17) | 0.76631 (16) | 0.59423 (15) | 0.0385 (6) | |
H27 | 1.4689 | 0.7852 | 0.5620 | 0.046* | |
C28 | 1.33498 (17) | 0.80203 (15) | 0.59014 (14) | 0.0358 (5) | |
H28 | 1.3329 | 0.8463 | 0.5550 | 0.043* | |
C29 | 1.25603 (17) | 0.77435 (15) | 0.63674 (14) | 0.0340 (5) | |
C30 | 1.2600 (2) | 0.71000 (17) | 0.68850 (19) | 0.0514 (7) | |
H30 | 1.2071 | 0.6901 | 0.7204 | 0.062* | |
C31 | 1.3412 (2) | 0.67522 (19) | 0.6933 (2) | 0.0570 (8) | |
H31 | 1.3444 | 0.6320 | 0.7294 | 0.068* | |
C32 | 1.09771 (16) | 0.81194 (14) | 0.67801 (14) | 0.0324 (5) | |
C33 | 0.95254 (16) | 0.87103 (15) | 0.70682 (15) | 0.0354 (5) | |
H33A | 0.9242 | 0.9204 | 0.6919 | 0.042* | |
H33B | 0.9625 | 0.8716 | 0.7593 | 0.042* | |
C34 | 0.89019 (16) | 0.80453 (15) | 0.70328 (14) | 0.0339 (5) | |
H34A | 0.8669 | 0.8123 | 0.6553 | 0.041* | |
H34B | 0.9244 | 0.7558 | 0.7037 | 0.041* | |
C35 | 0.73043 (16) | 0.83373 (15) | 0.75436 (14) | 0.0341 (5) | |
H35A | 0.7427 | 0.8774 | 0.7142 | 0.041* | |
H35B | 0.7013 | 0.8546 | 0.8012 | 0.041* | |
C36 | 0.66706 (18) | 0.77744 (16) | 0.73211 (16) | 0.0403 (6) | |
H36A | 0.6985 | 0.7515 | 0.6891 | 0.048* | |
H36B | 0.6482 | 0.7375 | 0.7749 | 0.048* | |
C37 | 0.51073 (17) | 0.81871 (15) | 0.76007 (15) | 0.0368 (5) | |
C38 | 0.35982 (17) | 0.87685 (15) | 0.75916 (14) | 0.0357 (5) | |
C39 | 0.31353 (17) | 0.93099 (15) | 0.71747 (14) | 0.0361 (5) | |
H39 | 0.3438 | 0.9566 | 0.6712 | 0.043* | |
C40 | 0.22548 (18) | 0.94750 (16) | 0.74230 (15) | 0.0393 (6) | |
H40 | 0.1946 | 0.9835 | 0.7131 | 0.047* | |
C41 | 0.18252 (18) | 0.91135 (18) | 0.80989 (16) | 0.0444 (6) | |
C42 | 0.2256 (2) | 0.8569 (2) | 0.85174 (17) | 0.0523 (8) | |
H42 | 0.1943 | 0.8314 | 0.8977 | 0.063* | |
C43 | 0.31411 (19) | 0.83923 (18) | 0.82708 (16) | 0.0457 (7) | |
H43 | 0.3437 | 0.8019 | 0.8559 | 0.055* | |
C44 | 0.81967 (16) | 0.76260 (14) | 0.83621 (14) | 0.0320 (5) | |
C45 | 0.92141 (16) | 0.68865 (14) | 0.91061 (14) | 0.0323 (5) | |
C46 | 0.85796 (18) | 0.66579 (15) | 0.97486 (15) | 0.0379 (6) | |
H46 | 0.7971 | 0.6798 | 0.9766 | 0.045* | |
C47 | 0.88410 (18) | 0.62279 (15) | 1.03564 (15) | 0.0389 (6) | |
H47 | 0.8416 | 0.6082 | 1.0799 | 0.047* | |
C48 | 0.97190 (18) | 0.60118 (14) | 1.03184 (14) | 0.0348 (5) | |
C49 | 1.03608 (17) | 0.62206 (15) | 0.96873 (14) | 0.0358 (5) | |
H49 | 1.0964 | 0.6061 | 0.9669 | 0.043* | |
C50 | 1.01033 (17) | 0.66647 (15) | 0.90874 (14) | 0.0353 (5) | |
H50 | 1.0537 | 0.6823 | 0.8654 | 0.042* | |
N19 | 0.25010 (15) | 0.49825 (13) | 0.23222 (13) | 0.0388 (5) | |
C51 | −0.0401 (2) | 0.47538 (19) | 0.33601 (18) | 0.0553 (8) | |
H51A | −0.1042 | 0.4634 | 0.3455 | 0.083* | |
H51B | −0.0290 | 0.5239 | 0.3032 | 0.083* | |
H51C | −0.0205 | 0.4804 | 0.3839 | 0.083* | |
C52 | 0.0109 (2) | 0.41156 (17) | 0.29828 (17) | 0.0466 (7) | |
H52A | −0.0015 | 0.4131 | 0.2463 | 0.056* | |
H52B | −0.0115 | 0.3616 | 0.3258 | 0.056* | |
C53 | 0.1128 (2) | 0.41542 (17) | 0.29455 (18) | 0.0490 (7) | |
H53A | 0.1264 | 0.4087 | 0.3463 | 0.059* | |
H53B | 0.1417 | 0.3730 | 0.2672 | 0.059* | |
C54 | 0.14972 (19) | 0.49192 (16) | 0.25485 (16) | 0.0419 (6) | |
H54A | 0.1231 | 0.5034 | 0.2089 | 0.050* | |
H54B | 0.1294 | 0.5324 | 0.2882 | 0.050* | |
C55 | 0.2823 (2) | 0.44540 (16) | 0.17047 (17) | 0.0441 (6) | |
H55A | 0.2651 | 0.3918 | 0.1909 | 0.053* | |
H55B | 0.2502 | 0.4596 | 0.1280 | 0.053* | |
C56 | 0.3813 (2) | 0.44747 (18) | 0.14002 (18) | 0.0501 (7) | |
H56A | 0.4141 | 0.4263 | 0.1802 | 0.060* | |
H56B | 0.4009 | 0.5015 | 0.1242 | 0.060* | |
C57 | 0.4029 (2) | 0.4010 (2) | 0.0735 (2) | 0.0617 (9) | |
H57A | 0.3746 | 0.4255 | 0.0318 | 0.074* | |
H57B | 0.3773 | 0.3486 | 0.0881 | 0.074* | |
C58 | 0.5029 (3) | 0.3949 (2) | 0.0461 (2) | 0.0718 (11) | |
H58A | 0.5136 | 0.3670 | 0.0012 | 0.108* | |
H58B | 0.5306 | 0.3669 | 0.0859 | 0.108* | |
H58C | 0.5290 | 0.4466 | 0.0335 | 0.108* | |
C59 | 0.2973 (2) | 0.47440 (17) | 0.29835 (17) | 0.0437 (6) | |
H59A | 0.2862 | 0.4187 | 0.3137 | 0.052* | |
H59B | 0.3624 | 0.4814 | 0.2807 | 0.052* | |
C60 | 0.2710 (2) | 0.51657 (19) | 0.36676 (18) | 0.0514 (7) | |
H60A | 0.2084 | 0.5036 | 0.3901 | 0.062* | |
H60B | 0.2747 | 0.5728 | 0.3515 | 0.062* | |
C61 | 0.3314 (3) | 0.4954 (2) | 0.4237 (2) | 0.0631 (9) | |
H61A | 0.3282 | 0.4389 | 0.4372 | 0.076* | |
H61B | 0.3936 | 0.5084 | 0.3993 | 0.076* | |
C62 | 0.3110 (4) | 0.5334 (3) | 0.4944 (2) | 0.0875 (14) | |
H62A | 0.3552 | 0.5178 | 0.5264 | 0.131* | |
H62B | 0.2512 | 0.5178 | 0.5214 | 0.131* | |
H62C | 0.3131 | 0.5894 | 0.4820 | 0.131* | |
C63 | 0.27396 (19) | 0.58148 (15) | 0.20295 (16) | 0.0415 (6) | |
H63A | 0.2445 | 0.6146 | 0.2410 | 0.050* | |
H63B | 0.3393 | 0.5879 | 0.1989 | 0.050* | |
C64 | 0.2492 (2) | 0.61080 (17) | 0.12773 (18) | 0.0501 (7) | |
H64A | 0.2855 | 0.5840 | 0.0875 | 0.060* | |
H64B | 0.1855 | 0.5991 | 0.1285 | 0.060* | |
C65 | 0.2646 (3) | 0.69612 (18) | 0.1108 (2) | 0.0595 (8) | |
H65A | 0.3254 | 0.7080 | 0.1189 | 0.071* | |
H65B | 0.2215 | 0.7226 | 0.1472 | 0.071* | |
C66 | 0.2553 (3) | 0.7282 (2) | 0.0323 (2) | 0.0682 (10) | |
H66A | 0.2710 | 0.7831 | 0.0246 | 0.102* | |
H66B | 0.1935 | 0.7219 | 0.0254 | 0.102* | |
H66C | 0.2954 | 0.7007 | −0.0043 | 0.102* | |
N20 | 0.72892 (17) | 0.93841 (15) | 1.01240 (14) | 0.0479 (6) | |
C67 | 0.8071 (2) | 0.93305 (19) | 1.05475 (17) | 0.0503 (7) | |
H67A | 0.8379 | 0.9837 | 1.0458 | 0.060* | |
H67B | 0.7829 | 0.9238 | 1.1094 | 0.060* | |
C68 | 0.8757 (2) | 0.8720 (2) | 1.03507 (18) | 0.0536 (8) | |
H68A | 0.8963 | 0.8771 | 0.9798 | 0.064* | |
H68B | 0.8478 | 0.8205 | 1.0502 | 0.064* | |
C69 | 0.9551 (2) | 0.8784 (2) | 1.07384 (18) | 0.0549 (8) | |
H69A | 0.9879 | 0.9267 | 1.0529 | 0.066* | |
H69B | 0.9334 | 0.8816 | 1.1282 | 0.066* | |
C70 | 1.0183 (2) | 0.8117 (2) | 1.0650 (2) | 0.0621 (9) | |
H70A | 1.0689 | 0.8195 | 1.0903 | 0.093* | |
H70B | 1.0404 | 0.8082 | 1.0113 | 0.093* | |
H70C | 0.9870 | 0.7638 | 1.0876 | 0.093* | |
C71 | 0.6633 (2) | 0.99719 (18) | 1.04517 (18) | 0.0527 (7) | |
H71A | 0.6200 | 1.0093 | 1.0107 | 0.063* | |
H71B | 0.6964 | 1.0452 | 1.0470 | 0.063* | |
C72 | 0.6114 (2) | 0.97207 (18) | 1.12398 (16) | 0.0494 (7) | |
H72A | 0.6021 | 0.9156 | 1.1297 | 0.059* | |
H72B | 0.6472 | 0.9842 | 1.1619 | 0.059* | |
C73 | 0.5216 (2) | 1.0113 (2) | 1.13913 (19) | 0.0559 (8) | |
H73A | 0.4876 | 1.0027 | 1.0989 | 0.067* | |
H73B | 0.5310 | 1.0675 | 1.1376 | 0.067* | |
C74 | 0.4670 (2) | 0.9813 (2) | 1.2154 (2) | 0.0633 (9) | |
H74A | 0.4089 | 1.0071 | 1.2223 | 0.095* | |
H74B | 0.4991 | 0.9920 | 1.2556 | 0.095* | |
H74C | 0.4580 | 0.9256 | 1.2173 | 0.095* | |
C75 | 0.6859 (2) | 0.86013 (17) | 1.01881 (17) | 0.0467 (7) | |
H75A | 0.7288 | 0.8256 | 0.9911 | 0.056* | |
H75B | 0.6750 | 0.8389 | 1.0726 | 0.056* | |
C76 | 0.5992 (2) | 0.85802 (19) | 0.98967 (18) | 0.0509 (7) | |
H76A | 0.6114 | 0.8659 | 0.9339 | 0.061* | |
H76B | 0.5603 | 0.9004 | 1.0081 | 0.061* | |
C77 | 0.5512 (2) | 0.7811 (2) | 1.0158 (2) | 0.0593 (8) | |
H77A | 0.5044 | 0.7754 | 0.9851 | 0.071* | |
H77B | 0.5946 | 0.7387 | 1.0071 | 0.071* | |
C78 | 0.5094 (3) | 0.7741 (3) | 1.0970 (3) | 0.0975 (16) | |
H78A | 0.4813 | 0.7232 | 1.1113 | 0.146* | |
H78B | 0.4640 | 0.8141 | 1.1055 | 0.146* | |
H78C | 0.5554 | 0.7803 | 1.1276 | 0.146* | |
C79 | 0.7611 (2) | 0.96494 (19) | 0.92815 (18) | 0.0598 (9) | |
H79A | 0.7876 | 0.9200 | 0.9036 | 0.072* | 0.5 |
H79B | 0.7080 | 0.9806 | 0.9055 | 0.072* | 0.5 |
H79C | 0.8093 | 0.9301 | 0.9082 | 0.072* | 0.5 |
H79D | 0.7109 | 0.9592 | 0.9010 | 0.072* | 0.5 |
C80A | 0.8284 (6) | 1.0305 (5) | 0.9088 (4) | 0.067 (3) | 0.5 |
H80A | 0.8051 | 1.0748 | 0.9359 | 0.080* | 0.5 |
H80B | 0.8849 | 1.0138 | 0.9256 | 0.080* | 0.5 |
C81A | 0.8466 (4) | 1.0550 (4) | 0.8248 (3) | 0.0606 (12) | 0.5 |
H81A | 0.8875 | 1.1000 | 0.8159 | 0.073* | 0.5 |
H81B | 0.8796 | 1.0127 | 0.8000 | 0.073* | 0.5 |
C82A | 0.7693 (6) | 1.0761 (7) | 0.7843 (6) | 0.090 (3) | 0.5 |
H82A | 0.7894 | 1.0765 | 0.7298 | 0.136* | 0.5 |
H82B | 0.7473 | 1.1274 | 0.7956 | 0.136* | 0.5 |
H82C | 0.7211 | 1.0382 | 0.8013 | 0.136* | 0.5 |
C80B | 0.7954 (6) | 1.0474 (3) | 0.9106 (4) | 0.067 (3) | 0.5 |
H80C | 0.7636 | 1.0778 | 0.9500 | 0.080* | 0.5 |
H80D | 0.8594 | 1.0472 | 0.9148 | 0.080* | 0.5 |
C81B | 0.7864 (5) | 1.0888 (4) | 0.8344 (3) | 0.0606 (12) | 0.5 |
H81C | 0.7231 | 1.1037 | 0.8355 | 0.073* | 0.5 |
H81D | 0.8224 | 1.1367 | 0.8259 | 0.073* | 0.5 |
C82B | 0.8152 (8) | 1.0424 (6) | 0.7690 (5) | 0.090 (3) | 0.5 |
H82D | 0.8166 | 1.0756 | 0.7216 | 0.136* | 0.5 |
H82E | 0.7729 | 1.0000 | 0.7716 | 0.136* | 0.5 |
H82F | 0.8750 | 1.0215 | 0.7711 | 0.136* | 0.5 |
P1 | 0.60995 (4) | 0.97408 (3) | 0.55144 (3) | 0.02832 (13) | |
O19 | 0.51551 (11) | 0.95514 (10) | 0.59024 (10) | 0.0354 (4) | |
O20 | 0.63474 (11) | 1.05356 (10) | 0.57479 (10) | 0.0344 (4) | |
H20O | 0.6934 (8) | 1.0670 (18) | 0.5542 (17) | 0.052* | |
O21 | 0.61479 (11) | 0.98453 (10) | 0.46370 (10) | 0.0333 (4) | |
H21O | 0.5645 (13) | 1.0068 (17) | 0.4480 (17) | 0.050* | |
O22 | 0.67758 (11) | 0.91334 (9) | 0.56726 (10) | 0.0327 (4) | |
P2 | 0.87010 (4) | 1.03192 (3) | 0.53218 (3) | 0.02841 (13) | |
O23 | 0.82990 (11) | 0.96052 (10) | 0.58748 (10) | 0.0338 (4) | |
H23O | 0.7761 (11) | 0.9427 (18) | 0.5783 (18) | 0.051* | |
O24 | 0.79916 (11) | 1.09098 (9) | 0.52118 (10) | 0.0335 (4) | |
O25 | 0.90787 (11) | 1.00351 (10) | 0.45455 (10) | 0.0332 (4) | |
H25O | 0.9644 (9) | 0.9823 (17) | 0.4529 (18) | 0.050* | |
O26 | 0.94470 (11) | 1.06344 (10) | 0.56654 (10) | 0.0363 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0425 (11) | 0.0716 (15) | 0.0544 (13) | 0.0122 (11) | −0.0132 (9) | −0.0063 (11) |
O2 | 0.0513 (13) | 0.0562 (13) | 0.0662 (14) | −0.0077 (10) | −0.0194 (11) | −0.0112 (11) |
O3 | 0.0413 (11) | 0.0482 (12) | 0.0658 (13) | 0.0115 (9) | −0.0135 (9) | −0.0266 (10) |
O4 | 0.0356 (10) | 0.0673 (14) | 0.0682 (14) | 0.0052 (9) | −0.0164 (10) | −0.0359 (11) |
O5 | 0.0706 (17) | 0.097 (2) | 0.0833 (19) | 0.0183 (15) | −0.0055 (14) | −0.0533 (17) |
O6 | 0.0820 (18) | 0.0580 (15) | 0.0704 (16) | 0.0327 (13) | 0.0133 (14) | −0.0017 (12) |
O7 | 0.0398 (10) | 0.0426 (10) | 0.0526 (11) | 0.0068 (8) | −0.0151 (8) | −0.0203 (9) |
O8 | 0.0359 (11) | 0.0642 (14) | 0.0735 (15) | 0.0015 (10) | −0.0116 (10) | 0.0110 (12) |
O9 | 0.0655 (15) | 0.0680 (15) | 0.0571 (14) | 0.0338 (12) | −0.0088 (11) | −0.0101 (12) |
N1 | 0.0373 (12) | 0.0530 (15) | 0.0434 (13) | −0.0048 (11) | −0.0037 (10) | 0.0035 (11) |
N2 | 0.0308 (11) | 0.0336 (11) | 0.0405 (11) | 0.0023 (9) | −0.0043 (9) | −0.0076 (9) |
N3 | 0.0324 (11) | 0.0358 (11) | 0.0468 (13) | 0.0048 (9) | −0.0065 (9) | −0.0107 (10) |
N4 | 0.0320 (11) | 0.0535 (14) | 0.0479 (13) | 0.0067 (10) | −0.0087 (10) | −0.0200 (11) |
N5 | 0.0424 (13) | 0.0403 (13) | 0.0554 (14) | 0.0086 (10) | −0.0197 (11) | −0.0189 (11) |
N6 | 0.0356 (11) | 0.0352 (11) | 0.0418 (12) | 0.0043 (9) | −0.0092 (9) | −0.0141 (9) |
N7 | 0.0406 (13) | 0.0557 (15) | 0.0413 (13) | 0.0100 (11) | 0.0003 (10) | 0.0085 (11) |
N8 | 0.0321 (11) | 0.0448 (13) | 0.0506 (13) | 0.0014 (9) | −0.0085 (10) | −0.0194 (11) |
N9 | 0.0563 (16) | 0.0452 (15) | 0.0639 (18) | 0.0001 (13) | 0.0136 (14) | −0.0143 (13) |
C1 | 0.0410 (15) | 0.0352 (14) | 0.0548 (17) | 0.0003 (11) | 0.0081 (12) | −0.0088 (12) |
C2 | 0.0508 (18) | 0.065 (2) | 0.061 (2) | 0.0011 (15) | −0.0077 (15) | −0.0305 (17) |
C3 | 0.0390 (16) | 0.065 (2) | 0.066 (2) | 0.0095 (14) | −0.0127 (14) | −0.0300 (16) |
C4 | 0.0345 (13) | 0.0362 (14) | 0.0482 (15) | −0.0044 (11) | −0.0007 (11) | −0.0106 (11) |
C5 | 0.0441 (15) | 0.0435 (15) | 0.0474 (16) | 0.0040 (12) | −0.0064 (12) | −0.0092 (12) |
C6 | 0.0453 (16) | 0.0409 (15) | 0.0534 (17) | 0.0081 (12) | −0.0018 (13) | −0.0028 (13) |
C7 | 0.0296 (13) | 0.0452 (15) | 0.0498 (15) | −0.0024 (11) | −0.0041 (11) | −0.0156 (12) |
C8 | 0.0336 (13) | 0.0435 (15) | 0.0445 (15) | 0.0042 (11) | −0.0086 (11) | −0.0127 (12) |
C9 | 0.0337 (13) | 0.0360 (13) | 0.0496 (15) | 0.0034 (11) | −0.0102 (11) | −0.0078 (11) |
C10 | 0.0298 (12) | 0.0346 (13) | 0.0410 (14) | 0.0020 (10) | −0.0006 (10) | −0.0036 (11) |
C11 | 0.0313 (12) | 0.0351 (13) | 0.0333 (12) | −0.0007 (10) | −0.0004 (10) | 0.0005 (10) |
C12 | 0.0361 (14) | 0.0365 (14) | 0.0465 (15) | 0.0034 (11) | −0.0038 (11) | −0.0064 (11) |
C13 | 0.0390 (14) | 0.0397 (14) | 0.0459 (15) | −0.0029 (11) | −0.0044 (11) | −0.0051 (12) |
C14 | 0.0312 (13) | 0.0439 (15) | 0.0372 (13) | −0.0040 (11) | −0.0030 (10) | 0.0017 (11) |
C15 | 0.0369 (14) | 0.0413 (15) | 0.0434 (14) | 0.0059 (11) | −0.0036 (11) | −0.0017 (12) |
C16 | 0.0396 (14) | 0.0371 (14) | 0.0411 (14) | 0.0034 (11) | −0.0052 (11) | −0.0057 (11) |
C17 | 0.0359 (14) | 0.0525 (16) | 0.0409 (14) | 0.0088 (12) | −0.0067 (11) | −0.0161 (12) |
C18 | 0.0399 (14) | 0.0448 (15) | 0.0456 (15) | 0.0082 (12) | −0.0134 (12) | −0.0140 (12) |
C19 | 0.0330 (13) | 0.0390 (14) | 0.0424 (14) | 0.0020 (10) | −0.0070 (11) | −0.0103 (11) |
C20 | 0.0367 (13) | 0.0355 (13) | 0.0298 (12) | 0.0032 (10) | −0.0041 (10) | −0.0045 (10) |
C21 | 0.0446 (15) | 0.0377 (14) | 0.0477 (15) | 0.0017 (12) | −0.0129 (12) | −0.0098 (12) |
C22 | 0.0515 (16) | 0.0366 (14) | 0.0453 (15) | 0.0098 (12) | −0.0086 (12) | −0.0086 (12) |
C23 | 0.0377 (14) | 0.0450 (15) | 0.0316 (12) | 0.0087 (11) | −0.0015 (10) | 0.0019 (11) |
C24 | 0.0364 (13) | 0.0458 (15) | 0.0337 (13) | −0.0031 (11) | −0.0081 (10) | −0.0012 (11) |
C25 | 0.0393 (14) | 0.0356 (13) | 0.0335 (12) | 0.0027 (10) | −0.0070 (10) | −0.0068 (10) |
O10A | 0.043 (2) | 0.098 (3) | 0.065 (3) | −0.001 (2) | −0.002 (2) | −0.017 (3) |
O11A | 0.043 (2) | 0.098 (3) | 0.065 (3) | −0.001 (2) | −0.002 (2) | −0.017 (3) |
O10B | 0.038 (2) | 0.058 (2) | 0.056 (2) | 0.0010 (16) | 0.0051 (16) | −0.0169 (18) |
O11B | 0.038 (2) | 0.058 (2) | 0.056 (2) | 0.0010 (16) | 0.0051 (16) | −0.0169 (18) |
O12 | 0.0471 (11) | 0.0621 (13) | 0.0424 (11) | 0.0037 (10) | −0.0108 (9) | 0.0127 (10) |
O13 | 0.0315 (9) | 0.0488 (11) | 0.0337 (9) | 0.0046 (8) | −0.0006 (7) | 0.0005 (8) |
O14 | 0.0855 (17) | 0.0689 (15) | 0.0343 (11) | 0.0219 (13) | −0.0013 (11) | 0.0100 (10) |
O15 | 0.0469 (12) | 0.0517 (12) | 0.0498 (11) | 0.0020 (9) | −0.0223 (9) | 0.0021 (9) |
O16 | 0.0326 (9) | 0.0421 (10) | 0.0364 (9) | 0.0011 (7) | −0.0039 (7) | 0.0060 (8) |
O17 | 0.0686 (17) | 0.089 (2) | 0.087 (2) | 0.0363 (15) | −0.0099 (14) | 0.0231 (16) |
O18 | 0.0383 (12) | 0.0599 (14) | 0.0859 (17) | 0.0104 (10) | −0.0055 (11) | −0.0102 (12) |
N10 | 0.0393 (14) | 0.084 (2) | 0.0456 (15) | −0.0057 (14) | 0.0019 (11) | −0.0091 (14) |
N11 | 0.0310 (11) | 0.0421 (12) | 0.0339 (11) | −0.0014 (9) | −0.0063 (8) | 0.0042 (9) |
N12 | 0.0318 (11) | 0.0423 (12) | 0.0429 (12) | 0.0022 (9) | −0.0107 (9) | 0.0048 (10) |
N13 | 0.0271 (10) | 0.0404 (11) | 0.0319 (10) | 0.0013 (8) | −0.0045 (8) | 0.0007 (9) |
N14 | 0.0322 (11) | 0.0359 (11) | 0.0366 (11) | 0.0002 (9) | −0.0017 (9) | 0.0057 (9) |
N15 | 0.0309 (10) | 0.0356 (11) | 0.0338 (11) | −0.0003 (9) | −0.0045 (8) | 0.0029 (9) |
N16 | 0.0477 (15) | 0.0517 (15) | 0.0648 (17) | 0.0146 (12) | −0.0133 (13) | −0.0084 (13) |
N17 | 0.0272 (10) | 0.0413 (12) | 0.0312 (10) | 0.0012 (9) | −0.0034 (8) | 0.0014 (9) |
N18 | 0.0530 (14) | 0.0345 (11) | 0.0365 (12) | −0.0021 (10) | −0.0141 (10) | −0.0017 (9) |
C26 | 0.0362 (14) | 0.0415 (15) | 0.0515 (16) | 0.0082 (11) | −0.0081 (12) | −0.0073 (12) |
C27 | 0.0315 (13) | 0.0465 (15) | 0.0378 (13) | −0.0002 (11) | −0.0053 (10) | −0.0070 (11) |
C28 | 0.0354 (13) | 0.0394 (14) | 0.0328 (12) | −0.0008 (11) | −0.0088 (10) | −0.0001 (10) |
C29 | 0.0331 (13) | 0.0338 (13) | 0.0358 (13) | 0.0010 (10) | −0.0069 (10) | −0.0055 (10) |
C30 | 0.0400 (15) | 0.0429 (16) | 0.0634 (19) | 0.0043 (12) | 0.0020 (13) | 0.0111 (14) |
C31 | 0.0521 (18) | 0.0437 (17) | 0.068 (2) | 0.0091 (14) | −0.0049 (15) | 0.0162 (15) |
C32 | 0.0301 (12) | 0.0344 (12) | 0.0332 (12) | −0.0031 (10) | −0.0075 (10) | −0.0022 (10) |
C33 | 0.0323 (13) | 0.0349 (13) | 0.0371 (13) | 0.0036 (10) | −0.0037 (10) | −0.0002 (10) |
C34 | 0.0320 (12) | 0.0395 (13) | 0.0297 (12) | 0.0044 (10) | −0.0064 (9) | −0.0005 (10) |
C35 | 0.0316 (12) | 0.0351 (13) | 0.0348 (12) | 0.0045 (10) | −0.0059 (10) | −0.0012 (10) |
C36 | 0.0364 (14) | 0.0374 (14) | 0.0491 (15) | 0.0041 (11) | −0.0147 (12) | −0.0017 (12) |
C37 | 0.0339 (13) | 0.0375 (13) | 0.0398 (14) | −0.0028 (10) | −0.0111 (10) | −0.0004 (11) |
C38 | 0.0323 (13) | 0.0411 (14) | 0.0347 (13) | −0.0048 (10) | −0.0081 (10) | −0.0045 (10) |
C39 | 0.0339 (13) | 0.0400 (14) | 0.0332 (12) | −0.0028 (10) | −0.0036 (10) | −0.0018 (10) |
C40 | 0.0348 (13) | 0.0419 (14) | 0.0430 (14) | −0.0008 (11) | −0.0099 (11) | −0.0074 (11) |
C41 | 0.0328 (14) | 0.0601 (18) | 0.0411 (14) | −0.0050 (12) | −0.0055 (11) | −0.0100 (13) |
C42 | 0.0404 (16) | 0.076 (2) | 0.0365 (14) | −0.0116 (15) | −0.0004 (12) | 0.0055 (14) |
C43 | 0.0394 (15) | 0.0570 (18) | 0.0391 (14) | −0.0046 (13) | −0.0094 (11) | 0.0066 (13) |
C44 | 0.0304 (12) | 0.0325 (12) | 0.0338 (12) | −0.0019 (10) | −0.0065 (10) | −0.0050 (10) |
C45 | 0.0329 (12) | 0.0317 (12) | 0.0331 (12) | −0.0006 (10) | −0.0081 (10) | −0.0035 (10) |
C46 | 0.0336 (13) | 0.0390 (14) | 0.0393 (14) | 0.0003 (11) | −0.0043 (10) | 0.0002 (11) |
C47 | 0.0417 (14) | 0.0373 (14) | 0.0354 (13) | −0.0029 (11) | −0.0027 (11) | 0.0006 (11) |
C48 | 0.0437 (14) | 0.0298 (12) | 0.0331 (12) | −0.0016 (10) | −0.0128 (10) | −0.0031 (10) |
C49 | 0.0328 (13) | 0.0392 (13) | 0.0373 (13) | 0.0016 (10) | −0.0108 (10) | −0.0059 (11) |
C50 | 0.0343 (13) | 0.0400 (14) | 0.0310 (12) | −0.0011 (10) | −0.0048 (10) | −0.0028 (10) |
N19 | 0.0423 (12) | 0.0335 (11) | 0.0428 (12) | −0.0016 (9) | −0.0144 (10) | −0.0027 (9) |
C51 | 0.062 (2) | 0.0517 (18) | 0.0486 (17) | 0.0078 (15) | −0.0042 (14) | 0.0006 (14) |
C52 | 0.0503 (17) | 0.0413 (15) | 0.0474 (16) | −0.0070 (13) | −0.0065 (13) | −0.0032 (12) |
C53 | 0.0538 (17) | 0.0398 (15) | 0.0518 (17) | 0.0016 (13) | −0.0064 (14) | −0.0022 (13) |
C54 | 0.0422 (15) | 0.0417 (15) | 0.0439 (15) | 0.0008 (12) | −0.0125 (12) | −0.0057 (12) |
C55 | 0.0520 (17) | 0.0333 (14) | 0.0476 (16) | −0.0013 (12) | −0.0117 (13) | −0.0025 (12) |
C56 | 0.0531 (18) | 0.0451 (16) | 0.0514 (17) | −0.0021 (13) | −0.0068 (14) | −0.0063 (13) |
C57 | 0.072 (2) | 0.0525 (19) | 0.0550 (19) | −0.0169 (17) | 0.0095 (16) | −0.0122 (15) |
C58 | 0.078 (3) | 0.055 (2) | 0.074 (2) | −0.0113 (18) | 0.017 (2) | −0.0163 (18) |
C59 | 0.0438 (15) | 0.0395 (14) | 0.0500 (16) | 0.0046 (12) | −0.0144 (12) | −0.0051 (12) |
C60 | 0.0599 (19) | 0.0481 (17) | 0.0492 (17) | 0.0090 (14) | −0.0157 (14) | −0.0102 (13) |
C61 | 0.074 (2) | 0.068 (2) | 0.0519 (19) | 0.0132 (18) | −0.0228 (17) | −0.0063 (16) |
C62 | 0.121 (4) | 0.084 (3) | 0.069 (3) | 0.029 (3) | −0.046 (3) | −0.015 (2) |
C63 | 0.0415 (14) | 0.0342 (13) | 0.0506 (16) | −0.0023 (11) | −0.0120 (12) | −0.0066 (12) |
C64 | 0.0552 (18) | 0.0417 (16) | 0.0541 (17) | −0.0067 (13) | −0.0153 (14) | 0.0022 (13) |
C65 | 0.074 (2) | 0.0414 (17) | 0.065 (2) | −0.0048 (15) | −0.0199 (17) | 0.0006 (15) |
C66 | 0.091 (3) | 0.0472 (19) | 0.063 (2) | 0.0067 (18) | −0.0140 (19) | 0.0076 (16) |
N20 | 0.0531 (15) | 0.0519 (14) | 0.0406 (13) | −0.0053 (11) | −0.0087 (11) | −0.0129 (11) |
C67 | 0.0523 (17) | 0.0582 (18) | 0.0408 (15) | −0.0126 (14) | −0.0053 (13) | −0.0096 (13) |
C68 | 0.0475 (17) | 0.063 (2) | 0.0480 (17) | −0.0132 (15) | 0.0014 (13) | −0.0117 (15) |
C69 | 0.0541 (18) | 0.061 (2) | 0.0472 (17) | −0.0120 (15) | −0.0005 (14) | −0.0053 (14) |
C70 | 0.057 (2) | 0.067 (2) | 0.060 (2) | −0.0052 (17) | −0.0065 (16) | −0.0035 (17) |
C71 | 0.067 (2) | 0.0455 (16) | 0.0501 (17) | −0.0005 (14) | −0.0205 (15) | −0.0084 (13) |
C72 | 0.0644 (19) | 0.0467 (16) | 0.0410 (15) | 0.0068 (14) | −0.0159 (14) | −0.0120 (13) |
C73 | 0.0595 (19) | 0.0573 (19) | 0.0587 (19) | 0.0093 (15) | −0.0258 (16) | −0.0168 (15) |
C74 | 0.060 (2) | 0.063 (2) | 0.069 (2) | 0.0039 (16) | −0.0069 (17) | −0.0198 (18) |
C75 | 0.0505 (17) | 0.0475 (16) | 0.0407 (15) | −0.0061 (13) | −0.0014 (12) | −0.0088 (12) |
C76 | 0.0552 (18) | 0.0539 (18) | 0.0446 (16) | −0.0024 (14) | −0.0098 (13) | −0.0079 (13) |
C77 | 0.0534 (19) | 0.0545 (19) | 0.071 (2) | −0.0091 (15) | −0.0126 (16) | −0.0060 (16) |
C78 | 0.082 (3) | 0.115 (4) | 0.088 (3) | −0.044 (3) | −0.011 (2) | 0.017 (3) |
C79 | 0.070 (2) | 0.068 (2) | 0.0420 (16) | −0.0177 (18) | −0.0090 (15) | −0.0090 (15) |
C80A | 0.053 (6) | 0.093 (4) | 0.052 (2) | −0.034 (4) | −0.006 (3) | −0.003 (3) |
C81A | 0.058 (3) | 0.063 (3) | 0.056 (3) | −0.008 (2) | 0.006 (2) | −0.006 (2) |
C82A | 0.093 (7) | 0.100 (8) | 0.070 (4) | −0.024 (5) | −0.010 (5) | 0.025 (4) |
C80B | 0.053 (6) | 0.093 (4) | 0.052 (2) | −0.034 (4) | −0.006 (3) | −0.003 (3) |
C81B | 0.058 (3) | 0.063 (3) | 0.056 (3) | −0.008 (2) | 0.006 (2) | −0.006 (2) |
C82B | 0.093 (7) | 0.100 (8) | 0.070 (4) | −0.024 (5) | −0.010 (5) | 0.025 (4) |
P1 | 0.0237 (3) | 0.0299 (3) | 0.0312 (3) | −0.0007 (2) | −0.0050 (2) | −0.0017 (2) |
O19 | 0.0295 (9) | 0.0420 (10) | 0.0336 (9) | −0.0027 (7) | −0.0072 (7) | 0.0043 (7) |
O20 | 0.0240 (8) | 0.0358 (9) | 0.0435 (10) | 0.0032 (7) | −0.0043 (7) | −0.0080 (7) |
O21 | 0.0270 (8) | 0.0365 (9) | 0.0352 (9) | 0.0010 (7) | −0.0034 (7) | −0.0015 (7) |
O22 | 0.0303 (8) | 0.0308 (9) | 0.0375 (9) | −0.0013 (7) | −0.0079 (7) | −0.0027 (7) |
P2 | 0.0229 (3) | 0.0267 (3) | 0.0354 (3) | 0.0013 (2) | −0.0054 (2) | −0.0021 (2) |
O23 | 0.0261 (8) | 0.0337 (9) | 0.0417 (9) | 0.0002 (7) | −0.0101 (7) | 0.0030 (7) |
O24 | 0.0271 (8) | 0.0296 (8) | 0.0425 (9) | 0.0008 (7) | −0.0043 (7) | −0.0006 (7) |
O25 | 0.0258 (8) | 0.0340 (9) | 0.0405 (9) | 0.0022 (7) | −0.0082 (7) | −0.0032 (7) |
O26 | 0.0292 (9) | 0.0341 (9) | 0.0475 (10) | 0.0042 (7) | −0.0074 (7) | −0.0117 (8) |
O1—N1 | 1.242 (3) | C46—H46 | 0.9500 |
O2—N1 | 1.226 (3) | C47—C48 | 1.374 (4) |
O3—C10 | 1.220 (3) | C47—H47 | 0.9500 |
O4—C7 | 1.219 (3) | C48—C49 | 1.385 (4) |
O5—N9 | 1.228 (4) | C49—C50 | 1.377 (4) |
O6—N9 | 1.217 (4) | C49—H49 | 0.9500 |
O7—C19 | 1.228 (3) | C50—H50 | 0.9500 |
O8—N7 | 1.225 (3) | N19—C54 | 1.511 (4) |
O9—N7 | 1.230 (3) | N19—C63 | 1.518 (3) |
N1—C14 | 1.450 (4) | N19—C59 | 1.521 (3) |
N2—C11 | 1.382 (3) | N19—C55 | 1.536 (4) |
N2—C10 | 1.394 (3) | C51—C52 | 1.504 (4) |
N2—H2N | 0.898 (5) | C51—H51A | 0.9800 |
N3—C10 | 1.345 (3) | C51—H51B | 0.9800 |
N3—C9 | 1.445 (3) | C51—H51C | 0.9800 |
N3—H3N | 0.897 (5) | C52—C53 | 1.541 (4) |
N4—C7 | 1.363 (3) | C52—H52A | 0.9900 |
N4—C17 | 1.455 (3) | C52—H52B | 0.9900 |
N4—C8 | 1.457 (3) | C53—C54 | 1.512 (4) |
N5—C19 | 1.354 (3) | C53—H53A | 0.9900 |
N5—C18 | 1.454 (3) | C53—H53B | 0.9900 |
N5—H5N | 0.899 (5) | C54—H54A | 0.9900 |
N6—C19 | 1.378 (3) | C54—H54B | 0.9900 |
N6—C20 | 1.394 (3) | C55—C56 | 1.509 (4) |
N6—H6N | 0.897 (5) | C55—H55A | 0.9900 |
N7—C23 | 1.464 (3) | C55—H55B | 0.9900 |
N8—C7 | 1.377 (4) | C56—C57 | 1.510 (4) |
N8—C4 | 1.403 (3) | C56—H56A | 0.9900 |
N8—H8N | 0.898 (5) | C56—H56B | 0.9900 |
N9—C1 | 1.465 (4) | C57—C58 | 1.520 (5) |
C1—C2 | 1.361 (5) | C57—H57A | 0.9900 |
C1—C6 | 1.373 (4) | C57—H57B | 0.9900 |
C2—C3 | 1.385 (4) | C58—H58A | 0.9800 |
C2—H2 | 0.9500 | C58—H58B | 0.9800 |
C3—C4 | 1.386 (4) | C58—H58C | 0.9800 |
C3—H3 | 0.9500 | C59—C60 | 1.501 (4) |
C4—C5 | 1.381 (4) | C59—H59A | 0.9900 |
C5—C6 | 1.382 (4) | C59—H59B | 0.9900 |
C5—H5 | 0.9500 | C60—C61 | 1.512 (4) |
C6—H6 | 0.9500 | C60—H60A | 0.9900 |
C8—C9 | 1.518 (4) | C60—H60B | 0.9900 |
C8—H8A | 0.9900 | C61—C62 | 1.488 (5) |
C8—H8B | 0.9900 | C61—H61A | 0.9900 |
C9—H9A | 0.9900 | C61—H61B | 0.9900 |
C9—H9B | 0.9900 | C62—H62A | 0.9800 |
C11—C12 | 1.402 (4) | C62—H62B | 0.9800 |
C11—C16 | 1.405 (4) | C62—H62C | 0.9800 |
C12—C13 | 1.377 (4) | C63—C64 | 1.512 (4) |
C12—H12 | 0.9500 | C63—H63A | 0.9900 |
C13—C14 | 1.382 (4) | C63—H63B | 0.9900 |
C13—H13 | 0.9500 | C64—C65 | 1.501 (4) |
C14—C15 | 1.381 (4) | C64—H64A | 0.9900 |
C15—C16 | 1.372 (4) | C64—H64B | 0.9900 |
C15—H15 | 0.9500 | C65—C66 | 1.501 (5) |
C16—H16 | 0.9500 | C65—H65A | 0.9900 |
C17—C18 | 1.523 (4) | C65—H65B | 0.9900 |
C17—H17A | 0.9900 | C66—H66A | 0.9800 |
C17—H17B | 0.9900 | C66—H66B | 0.9800 |
C18—H18A | 0.9900 | C66—H66C | 0.9800 |
C18—H18B | 0.9900 | N20—C75 | 1.507 (4) |
C20—C21 | 1.398 (4) | N20—C71 | 1.515 (4) |
C20—C25 | 1.399 (4) | N20—C67 | 1.522 (4) |
C21—C22 | 1.382 (4) | N20—C79 | 1.541 (4) |
C21—H21 | 0.9500 | C67—C68 | 1.507 (5) |
C22—C23 | 1.374 (4) | C67—H67A | 0.9900 |
C22—H22 | 0.9500 | C67—H67B | 0.9900 |
C23—C24 | 1.380 (4) | C68—C69 | 1.511 (5) |
C24—C25 | 1.379 (4) | C68—H68A | 0.9900 |
C24—H24 | 0.9500 | C68—H68B | 0.9900 |
C25—H25 | 0.9500 | C69—C70 | 1.504 (5) |
O10A—N10 | 1.250 (3) | C69—H69A | 0.9900 |
O11A—N10 | 1.224 (4) | C69—H69B | 0.9900 |
O10B—N10 | 1.230 (3) | C70—H70A | 0.9800 |
O11B—N10 | 1.232 (3) | C70—H70B | 0.9800 |
O12—C37 | 1.216 (3) | C70—H70C | 0.9800 |
O13—C44 | 1.227 (3) | C71—C72 | 1.527 (4) |
O14—N18 | 1.223 (3) | C71—H71A | 0.9900 |
O15—N18 | 1.225 (3) | C71—H71B | 0.9900 |
O16—C32 | 1.231 (3) | C72—C73 | 1.513 (4) |
O17—N16 | 1.224 (4) | C72—H72A | 0.9900 |
O18—N16 | 1.222 (4) | C72—H72B | 0.9900 |
N10—C41 | 1.451 (4) | C73—C74 | 1.524 (5) |
N11—C38 | 1.381 (3) | C73—H73A | 0.9900 |
N11—C37 | 1.391 (3) | C73—H73B | 0.9900 |
N11—H11N | 0.899 (5) | C74—H74A | 0.9800 |
N12—C37 | 1.354 (3) | C74—H74B | 0.9800 |
N12—C36 | 1.448 (3) | C74—H74C | 0.9800 |
N12—H12N | 0.897 (5) | C75—C76 | 1.506 (4) |
N13—C44 | 1.359 (3) | C75—H75A | 0.9900 |
N13—C34 | 1.463 (3) | C75—H75B | 0.9900 |
N13—C35 | 1.463 (3) | C76—C77 | 1.526 (4) |
N14—C32 | 1.350 (3) | C76—H76A | 0.9900 |
N14—C33 | 1.451 (3) | C76—H76B | 0.9900 |
N14—H14N | 0.898 (5) | C77—C78 | 1.489 (6) |
N15—C32 | 1.379 (3) | C77—H77A | 0.9900 |
N15—C29 | 1.393 (3) | C77—H77B | 0.9900 |
N15—H15N | 0.897 (5) | C78—H78A | 0.9800 |
N16—C26 | 1.463 (4) | C78—H78B | 0.9800 |
N17—C44 | 1.382 (3) | C78—H78C | 0.9800 |
N17—C45 | 1.404 (3) | C79—C80A | 1.516 (4) |
N17—H17N | 0.898 (5) | C79—C80B | 1.519 (4) |
N18—C48 | 1.461 (3) | C79—H79A | 0.9900 |
C26—C27 | 1.374 (4) | C79—H79B | 0.9900 |
C26—C31 | 1.379 (4) | C79—H79C | 0.9900 |
C27—C28 | 1.379 (4) | C79—H79D | 0.9900 |
C27—H27 | 0.9500 | C80A—C81A | 1.514 (4) |
C28—C29 | 1.399 (4) | C80A—H80A | 0.9900 |
C28—H28 | 0.9500 | C80A—H80B | 0.9900 |
C29—C30 | 1.391 (4) | C81A—C82A | 1.513 (4) |
C30—C31 | 1.381 (4) | C81A—H81A | 0.9900 |
C30—H30 | 0.9500 | C81A—H81B | 0.9900 |
C31—H31 | 0.9500 | C82A—H82A | 0.9800 |
C33—C34 | 1.523 (4) | C82A—H82B | 0.9800 |
C33—H33A | 0.9900 | C82A—H82C | 0.9800 |
C33—H33B | 0.9900 | C80B—C81B | 1.515 (4) |
C34—H34A | 0.9900 | C80B—H80C | 0.9900 |
C34—H34B | 0.9900 | C80B—H80D | 0.9900 |
C35—C36 | 1.519 (4) | C81B—C82B | 1.506 (4) |
C35—H35A | 0.9900 | C81B—H81C | 0.9900 |
C35—H35B | 0.9900 | C81B—H81D | 0.9900 |
C36—H36A | 0.9900 | C82B—H82D | 0.9800 |
C36—H36B | 0.9900 | C82B—H82E | 0.9800 |
C38—C43 | 1.402 (4) | C82B—H82F | 0.9800 |
C38—C39 | 1.405 (4) | P1—O22 | 1.5071 (17) |
C39—C40 | 1.372 (4) | P1—O19 | 1.5072 (17) |
C39—H39 | 0.9500 | P1—O20 | 1.5632 (18) |
C40—C41 | 1.374 (4) | P1—O21 | 1.5695 (18) |
C40—H40 | 0.9500 | O20—H20O | 0.928 (5) |
C41—C42 | 1.383 (4) | O21—H21O | 0.928 (5) |
C42—C43 | 1.382 (4) | P2—O24 | 1.5054 (17) |
C42—H42 | 0.9500 | P2—O26 | 1.5226 (18) |
C43—H43 | 0.9500 | P2—O25 | 1.5531 (18) |
C45—C50 | 1.397 (4) | P2—O23 | 1.5705 (18) |
C45—C46 | 1.400 (4) | O23—H23O | 0.927 (5) |
C46—C47 | 1.379 (4) | O25—H25O | 0.928 (5) |
O2—N1—O1 | 122.6 (3) | C52—C51—H51B | 109.5 |
O2—N1—C14 | 119.2 (2) | H51A—C51—H51B | 109.5 |
O1—N1—C14 | 118.1 (3) | C52—C51—H51C | 109.5 |
C11—N2—C10 | 127.4 (2) | H51A—C51—H51C | 109.5 |
C11—N2—H2N | 118 (2) | H51B—C51—H51C | 109.5 |
C10—N2—H2N | 115 (2) | C51—C52—C53 | 114.4 (3) |
C10—N3—C9 | 121.4 (2) | C51—C52—H52A | 108.7 |
C10—N3—H3N | 123 (2) | C53—C52—H52A | 108.7 |
C9—N3—H3N | 116 (2) | C51—C52—H52B | 108.7 |
C7—N4—C17 | 123.5 (2) | C53—C52—H52B | 108.7 |
C7—N4—C8 | 118.8 (2) | H52A—C52—H52B | 107.6 |
C17—N4—C8 | 117.8 (2) | C54—C53—C52 | 110.6 (2) |
C19—N5—C18 | 119.6 (2) | C54—C53—H53A | 109.5 |
C19—N5—H5N | 118 (2) | C52—C53—H53A | 109.5 |
C18—N5—H5N | 120 (2) | C54—C53—H53B | 109.5 |
C19—N6—C20 | 126.8 (2) | C52—C53—H53B | 109.5 |
C19—N6—H6N | 115 (2) | H53A—C53—H53B | 108.1 |
C20—N6—H6N | 118 (2) | N19—C54—C53 | 116.7 (2) |
O8—N7—O9 | 123.9 (3) | N19—C54—H54A | 108.1 |
O8—N7—C23 | 118.4 (3) | C53—C54—H54A | 108.1 |
O9—N7—C23 | 117.7 (3) | N19—C54—H54B | 108.1 |
C7—N8—C4 | 126.1 (2) | C53—C54—H54B | 108.1 |
C7—N8—H8N | 120 (2) | H54A—C54—H54B | 107.3 |
C4—N8—H8N | 113 (2) | C56—C55—N19 | 115.7 (2) |
O6—N9—O5 | 123.8 (3) | C56—C55—H55A | 108.3 |
O6—N9—C1 | 118.4 (3) | N19—C55—H55A | 108.3 |
O5—N9—C1 | 117.8 (3) | C56—C55—H55B | 108.3 |
C2—C1—C6 | 121.9 (3) | N19—C55—H55B | 108.3 |
C2—C1—N9 | 118.9 (3) | H55A—C55—H55B | 107.4 |
C6—C1—N9 | 119.2 (3) | C55—C56—C57 | 110.7 (3) |
C1—C2—C3 | 119.6 (3) | C55—C56—H56A | 109.5 |
C1—C2—H2 | 120.2 | C57—C56—H56A | 109.5 |
C3—C2—H2 | 120.2 | C55—C56—H56B | 109.5 |
C2—C3—C4 | 120.0 (3) | C57—C56—H56B | 109.5 |
C2—C3—H3 | 120.0 | H56A—C56—H56B | 108.1 |
C4—C3—H3 | 120.0 | C56—C57—C58 | 112.4 (3) |
C5—C4—C3 | 119.1 (3) | C56—C57—H57A | 109.1 |
C5—C4—N8 | 117.2 (3) | C58—C57—H57A | 109.1 |
C3—C4—N8 | 123.7 (3) | C56—C57—H57B | 109.1 |
C4—C5—C6 | 121.1 (3) | C58—C57—H57B | 109.1 |
C4—C5—H5 | 119.5 | H57A—C57—H57B | 107.9 |
C6—C5—H5 | 119.5 | C57—C58—H58A | 109.5 |
C1—C6—C5 | 118.4 (3) | C57—C58—H58B | 109.5 |
C1—C6—H6 | 120.8 | H58A—C58—H58B | 109.5 |
C5—C6—H6 | 120.8 | C57—C58—H58C | 109.5 |
O4—C7—N4 | 121.4 (3) | H58A—C58—H58C | 109.5 |
O4—C7—N8 | 122.6 (2) | H58B—C58—H58C | 109.5 |
N4—C7—N8 | 116.0 (2) | C60—C59—N19 | 116.4 (2) |
N4—C8—C9 | 112.0 (2) | C60—C59—H59A | 108.2 |
N4—C8—H8A | 109.2 | N19—C59—H59A | 108.2 |
C9—C8—H8A | 109.2 | C60—C59—H59B | 108.2 |
N4—C8—H8B | 109.2 | N19—C59—H59B | 108.2 |
C9—C8—H8B | 109.2 | H59A—C59—H59B | 107.3 |
H8A—C8—H8B | 107.9 | C59—C60—C61 | 111.0 (3) |
N3—C9—C8 | 111.5 (2) | C59—C60—H60A | 109.4 |
N3—C9—H9A | 109.3 | C61—C60—H60A | 109.4 |
C8—C9—H9A | 109.3 | C59—C60—H60B | 109.4 |
N3—C9—H9B | 109.3 | C61—C60—H60B | 109.4 |
C8—C9—H9B | 109.3 | H60A—C60—H60B | 108.0 |
H9A—C9—H9B | 108.0 | C62—C61—C60 | 115.8 (3) |
O3—C10—N3 | 123.7 (2) | C62—C61—H61A | 108.3 |
O3—C10—N2 | 123.2 (2) | C60—C61—H61A | 108.3 |
N3—C10—N2 | 113.1 (2) | C62—C61—H61B | 108.3 |
N2—C11—C12 | 124.3 (2) | C60—C61—H61B | 108.3 |
N2—C11—C16 | 117.3 (2) | H61A—C61—H61B | 107.4 |
C12—C11—C16 | 118.4 (2) | C61—C62—H62A | 109.5 |
C13—C12—C11 | 120.2 (3) | C61—C62—H62B | 109.5 |
C13—C12—H12 | 119.9 | H62A—C62—H62B | 109.5 |
C11—C12—H12 | 119.9 | C61—C62—H62C | 109.5 |
C12—C13—C14 | 119.9 (3) | H62A—C62—H62C | 109.5 |
C12—C13—H13 | 120.1 | H62B—C62—H62C | 109.5 |
C14—C13—H13 | 120.1 | C64—C63—N19 | 116.6 (2) |
C15—C14—C13 | 121.1 (3) | C64—C63—H63A | 108.1 |
C15—C14—N1 | 119.3 (2) | N19—C63—H63A | 108.1 |
C13—C14—N1 | 119.5 (3) | C64—C63—H63B | 108.1 |
C16—C15—C14 | 119.2 (3) | N19—C63—H63B | 108.1 |
C16—C15—H15 | 120.4 | H63A—C63—H63B | 107.3 |
C14—C15—H15 | 120.4 | C65—C64—C63 | 111.0 (3) |
C15—C16—C11 | 121.1 (3) | C65—C64—H64A | 109.4 |
C15—C16—H16 | 119.4 | C63—C64—H64A | 109.4 |
C11—C16—H16 | 119.4 | C65—C64—H64B | 109.4 |
N4—C17—C18 | 112.3 (2) | C63—C64—H64B | 109.4 |
N4—C17—H17A | 109.2 | H64A—C64—H64B | 108.0 |
C18—C17—H17A | 109.2 | C64—C65—C66 | 114.6 (3) |
N4—C17—H17B | 109.2 | C64—C65—H65A | 108.6 |
C18—C17—H17B | 109.2 | C66—C65—H65A | 108.6 |
H17A—C17—H17B | 107.9 | C64—C65—H65B | 108.6 |
N5—C18—C17 | 111.0 (2) | C66—C65—H65B | 108.6 |
N5—C18—H18A | 109.4 | H65A—C65—H65B | 107.6 |
C17—C18—H18A | 109.4 | C65—C66—H66A | 109.5 |
N5—C18—H18B | 109.4 | C65—C66—H66B | 109.5 |
C17—C18—H18B | 109.4 | H66A—C66—H66B | 109.5 |
H18A—C18—H18B | 108.0 | C65—C66—H66C | 109.5 |
O7—C19—N5 | 122.3 (2) | H66A—C66—H66C | 109.5 |
O7—C19—N6 | 124.2 (2) | H66B—C66—H66C | 109.5 |
N5—C19—N6 | 113.6 (2) | C75—N20—C71 | 111.4 (2) |
N6—C20—C21 | 123.7 (2) | C75—N20—C67 | 109.4 (2) |
N6—C20—C25 | 117.3 (2) | C71—N20—C67 | 108.7 (2) |
C21—C20—C25 | 119.0 (2) | C75—N20—C79 | 108.2 (2) |
C22—C21—C20 | 119.5 (3) | C71—N20—C79 | 108.4 (3) |
C22—C21—H21 | 120.3 | C67—N20—C79 | 110.7 (2) |
C20—C21—H21 | 120.3 | C68—C67—N20 | 116.6 (3) |
C23—C22—C21 | 120.3 (3) | C68—C67—H67A | 108.1 |
C23—C22—H22 | 119.8 | N20—C67—H67A | 108.1 |
C21—C22—H22 | 119.8 | C68—C67—H67B | 108.1 |
C22—C23—C24 | 121.4 (3) | N20—C67—H67B | 108.1 |
C22—C23—N7 | 119.7 (3) | H67A—C67—H67B | 107.3 |
C24—C23—N7 | 118.9 (3) | C67—C68—C69 | 111.7 (3) |
C25—C24—C23 | 118.6 (2) | C67—C68—H68A | 109.3 |
C25—C24—H24 | 120.7 | C69—C68—H68A | 109.3 |
C23—C24—H24 | 120.7 | C67—C68—H68B | 109.3 |
C24—C25—C20 | 121.2 (2) | C69—C68—H68B | 109.3 |
C24—C25—H25 | 119.4 | H68A—C68—H68B | 107.9 |
C20—C25—H25 | 119.4 | C70—C69—C68 | 113.2 (3) |
O10B—N10—O11B | 121.8 (4) | C70—C69—H69A | 108.9 |
O11A—N10—O10A | 120.6 (5) | C68—C69—H69A | 108.9 |
O11A—N10—C41 | 121.8 (5) | C70—C69—H69B | 108.9 |
O10B—N10—C41 | 119.6 (3) | C68—C69—H69B | 108.9 |
O11B—N10—C41 | 115.9 (4) | H69A—C69—H69B | 107.8 |
O10A—N10—C41 | 115.8 (3) | C69—C70—H70A | 109.5 |
C38—N11—C37 | 128.6 (2) | C69—C70—H70B | 109.5 |
C38—N11—H11N | 116 (2) | H70A—C70—H70B | 109.5 |
C37—N11—H11N | 115 (2) | C69—C70—H70C | 109.5 |
C37—N12—C36 | 122.4 (2) | H70A—C70—H70C | 109.5 |
C37—N12—H12N | 122 (2) | H70B—C70—H70C | 109.5 |
C36—N12—H12N | 115 (2) | N20—C71—C72 | 115.0 (3) |
C44—N13—C34 | 124.1 (2) | N20—C71—H71A | 108.5 |
C44—N13—C35 | 117.9 (2) | C72—C71—H71A | 108.5 |
C34—N13—C35 | 117.95 (19) | N20—C71—H71B | 108.5 |
C32—N14—C33 | 119.4 (2) | C72—C71—H71B | 108.5 |
C32—N14—H14N | 120 (2) | H71A—C71—H71B | 107.5 |
C33—N14—H14N | 118 (2) | C73—C72—C71 | 112.4 (3) |
C32—N15—C29 | 128.0 (2) | C73—C72—H72A | 109.1 |
C32—N15—H15N | 115 (2) | C71—C72—H72A | 109.1 |
C29—N15—H15N | 117 (2) | C73—C72—H72B | 109.1 |
O18—N16—O17 | 123.3 (3) | C71—C72—H72B | 109.1 |
O18—N16—C26 | 118.7 (3) | H72A—C72—H72B | 107.9 |
O17—N16—C26 | 118.0 (3) | C72—C73—C74 | 112.1 (3) |
C44—N17—C45 | 126.4 (2) | C72—C73—H73A | 109.2 |
C44—N17—H17N | 118.8 (19) | C74—C73—H73A | 109.2 |
C45—N17—H17N | 114.6 (19) | C72—C73—H73B | 109.2 |
O14—N18—O15 | 123.2 (2) | C74—C73—H73B | 109.2 |
O14—N18—C48 | 118.2 (2) | H73A—C73—H73B | 107.9 |
O15—N18—C48 | 118.6 (2) | C73—C74—H74A | 109.5 |
C27—C26—C31 | 121.1 (3) | C73—C74—H74B | 109.5 |
C27—C26—N16 | 119.2 (3) | H74A—C74—H74B | 109.5 |
C31—C26—N16 | 119.7 (3) | C73—C74—H74C | 109.5 |
C26—C27—C28 | 118.8 (2) | H74A—C74—H74C | 109.5 |
C26—C27—H27 | 120.6 | H74B—C74—H74C | 109.5 |
C28—C27—H27 | 120.6 | C76—C75—N20 | 115.8 (3) |
C27—C28—C29 | 121.3 (2) | C76—C75—H75A | 108.3 |
C27—C28—H28 | 119.4 | N20—C75—H75A | 108.3 |
C29—C28—H28 | 119.4 | C76—C75—H75B | 108.3 |
C30—C29—N15 | 124.3 (2) | N20—C75—H75B | 108.3 |
C30—C29—C28 | 118.9 (2) | H75A—C75—H75B | 107.4 |
N15—C29—C28 | 116.8 (2) | C75—C76—C77 | 110.9 (3) |
C31—C30—C29 | 119.7 (3) | C75—C76—H76A | 109.5 |
C31—C30—H30 | 120.2 | C77—C76—H76A | 109.5 |
C29—C30—H30 | 120.2 | C75—C76—H76B | 109.5 |
C26—C31—C30 | 120.3 (3) | C77—C76—H76B | 109.5 |
C26—C31—H31 | 119.8 | H76A—C76—H76B | 108.1 |
C30—C31—H31 | 119.8 | C78—C77—C76 | 112.7 (3) |
O16—C32—N14 | 122.2 (2) | C78—C77—H77A | 109.1 |
O16—C32—N15 | 124.3 (2) | C76—C77—H77A | 109.1 |
N14—C32—N15 | 113.6 (2) | C78—C77—H77B | 109.1 |
N14—C33—C34 | 111.3 (2) | C76—C77—H77B | 109.1 |
N14—C33—H33A | 109.4 | H77A—C77—H77B | 107.8 |
C34—C33—H33A | 109.4 | C77—C78—H78A | 109.5 |
N14—C33—H33B | 109.4 | C77—C78—H78B | 109.5 |
C34—C33—H33B | 109.4 | H78A—C78—H78B | 109.5 |
H33A—C33—H33B | 108.0 | C77—C78—H78C | 109.5 |
N13—C34—C33 | 112.3 (2) | H78A—C78—H78C | 109.5 |
N13—C34—H34A | 109.2 | H78B—C78—H78C | 109.5 |
C33—C34—H34A | 109.2 | C80A—C79—N20 | 117.2 (3) |
N13—C34—H34B | 109.2 | C80B—C79—N20 | 115.3 (4) |
C33—C34—H34B | 109.2 | C80A—C79—H79A | 108.0 |
H34A—C34—H34B | 107.9 | N20—C79—H79A | 108.0 |
N13—C35—C36 | 112.4 (2) | C80A—C79—H79B | 108.0 |
N13—C35—H35A | 109.1 | N20—C79—H79B | 108.0 |
C36—C35—H35A | 109.1 | H79A—C79—H79B | 107.2 |
N13—C35—H35B | 109.1 | C80B—C79—H79C | 108.5 |
C36—C35—H35B | 109.1 | N20—C79—H79C | 108.5 |
H35A—C35—H35B | 107.9 | C80B—C79—H79D | 108.5 |
N12—C36—C35 | 111.2 (2) | N20—C79—H79D | 108.5 |
N12—C36—H36A | 109.4 | H79C—C79—H79D | 107.5 |
C35—C36—H36A | 109.4 | C81A—C80A—C79 | 111.0 (5) |
N12—C36—H36B | 109.4 | C81A—C80A—H80A | 109.4 |
C35—C36—H36B | 109.4 | C79—C80A—H80A | 109.4 |
H36A—C36—H36B | 108.0 | C81A—C80A—H80B | 109.4 |
O12—C37—N12 | 124.5 (2) | C79—C80A—H80B | 109.4 |
O12—C37—N11 | 123.9 (2) | H80A—C80A—H80B | 108.0 |
N12—C37—N11 | 111.6 (2) | C82A—C81A—C80A | 119.5 (7) |
N11—C38—C43 | 124.9 (2) | C82A—C81A—H81A | 107.4 |
N11—C38—C39 | 116.5 (2) | C80A—C81A—H81A | 107.4 |
C43—C38—C39 | 118.7 (2) | C82A—C81A—H81B | 107.4 |
C40—C39—C38 | 121.2 (2) | C80A—C81A—H81B | 107.4 |
C40—C39—H39 | 119.4 | H81A—C81A—H81B | 107.0 |
C38—C39—H39 | 119.4 | C81A—C82A—H82A | 109.5 |
C39—C40—C41 | 119.2 (3) | C81A—C82A—H82B | 109.5 |
C39—C40—H40 | 120.4 | H82A—C82A—H82B | 109.5 |
C41—C40—H40 | 120.4 | C81A—C82A—H82C | 109.5 |
C40—C41—C42 | 121.1 (3) | H82A—C82A—H82C | 109.5 |
C40—C41—N10 | 119.0 (3) | H82B—C82A—H82C | 109.5 |
C42—C41—N10 | 119.9 (3) | C81B—C80B—C79 | 117.2 (5) |
C43—C42—C41 | 120.3 (3) | C81B—C80B—H80C | 108.0 |
C43—C42—H42 | 119.9 | C79—C80B—H80C | 108.0 |
C41—C42—H42 | 119.9 | C81B—C80B—H80D | 108.0 |
C42—C43—C38 | 119.5 (3) | C79—C80B—H80D | 108.0 |
C42—C43—H43 | 120.3 | H80C—C80B—H80D | 107.2 |
C38—C43—H43 | 120.3 | C82B—C81B—C80B | 114.5 (7) |
O13—C44—N13 | 121.2 (2) | C82B—C81B—H81C | 108.6 |
O13—C44—N17 | 122.9 (2) | C80B—C81B—H81C | 108.6 |
N13—C44—N17 | 115.9 (2) | C82B—C81B—H81D | 108.6 |
C50—C45—C46 | 119.2 (2) | C80B—C81B—H81D | 108.6 |
C50—C45—N17 | 116.4 (2) | H81C—C81B—H81D | 107.6 |
C46—C45—N17 | 124.3 (2) | C81B—C82B—H82D | 109.5 |
C47—C46—C45 | 119.8 (2) | C81B—C82B—H82E | 109.5 |
C47—C46—H46 | 120.1 | H82D—C82B—H82E | 109.5 |
C45—C46—H46 | 120.1 | C81B—C82B—H82F | 109.5 |
C48—C47—C46 | 119.6 (2) | H82D—C82B—H82F | 109.5 |
C48—C47—H47 | 120.2 | H82E—C82B—H82F | 109.5 |
C46—C47—H47 | 120.2 | O22—P1—O19 | 114.54 (10) |
C47—C48—C49 | 122.0 (2) | O22—P1—O20 | 111.33 (9) |
C47—C48—N18 | 119.6 (2) | O19—P1—O20 | 107.35 (10) |
C49—C48—N18 | 118.5 (2) | O22—P1—O21 | 106.44 (10) |
C50—C49—C48 | 118.3 (2) | O19—P1—O21 | 109.89 (9) |
C50—C49—H49 | 120.8 | O20—P1—O21 | 107.06 (10) |
C48—C49—H49 | 120.8 | P1—O20—H20O | 111 (2) |
C49—C50—C45 | 121.0 (2) | P1—O21—H21O | 115 (2) |
C49—C50—H50 | 119.5 | O24—P2—O26 | 112.39 (10) |
C45—C50—H50 | 119.5 | O24—P2—O25 | 108.25 (10) |
C54—N19—C63 | 108.4 (2) | O26—P2—O25 | 110.73 (10) |
C54—N19—C59 | 111.8 (2) | O24—P2—O23 | 110.98 (9) |
C63—N19—C59 | 108.9 (2) | O26—P2—O23 | 106.28 (10) |
C54—N19—C55 | 109.5 (2) | O25—P2—O23 | 108.14 (10) |
C63—N19—C55 | 110.2 (2) | P2—O23—H23O | 114 (2) |
C59—N19—C55 | 108.1 (2) | P2—O25—H25O | 113 (2) |
C52—C51—H51A | 109.5 | ||
O6—N9—C1—C2 | −166.3 (3) | C37—N12—C36—C35 | −97.3 (3) |
O5—N9—C1—C2 | 14.0 (4) | N13—C35—C36—N12 | −172.7 (2) |
O6—N9—C1—C6 | 12.2 (4) | C36—N12—C37—O12 | −4.5 (4) |
O5—N9—C1—C6 | −167.5 (3) | C36—N12—C37—N11 | 175.5 (2) |
C6—C1—C2—C3 | −1.0 (5) | C38—N11—C37—O12 | −4.1 (5) |
N9—C1—C2—C3 | 177.5 (3) | C38—N11—C37—N12 | 175.9 (2) |
C1—C2—C3—C4 | 1.4 (5) | C37—N11—C38—C43 | −6.0 (4) |
C2—C3—C4—C5 | −0.9 (5) | C37—N11—C38—C39 | 174.8 (3) |
C2—C3—C4—N8 | 177.3 (3) | N11—C38—C39—C40 | 179.6 (2) |
C7—N8—C4—C5 | −172.6 (3) | C43—C38—C39—C40 | 0.3 (4) |
C7—N8—C4—C3 | 9.2 (5) | C38—C39—C40—C41 | 1.2 (4) |
C3—C4—C5—C6 | −0.1 (4) | C39—C40—C41—C42 | −2.3 (4) |
N8—C4—C5—C6 | −178.3 (3) | C39—C40—C41—N10 | 178.7 (3) |
C2—C1—C6—C5 | 0.0 (5) | O11A—N10—C41—C40 | −2.6 (11) |
N9—C1—C6—C5 | −178.4 (3) | O10B—N10—C41—C40 | −162.2 (4) |
C4—C5—C6—C1 | 0.5 (4) | O11B—N10—C41—C40 | −0.6 (9) |
C17—N4—C7—O4 | 175.2 (3) | O10A—N10—C41—C40 | 161.9 (4) |
C8—N4—C7—O4 | −4.5 (4) | O11A—N10—C41—C42 | 178.3 (10) |
C17—N4—C7—N8 | −4.0 (4) | O10B—N10—C41—C42 | 18.8 (5) |
C8—N4—C7—N8 | 176.4 (2) | O11B—N10—C41—C42 | −179.6 (8) |
C4—N8—C7—O4 | 4.9 (5) | O10A—N10—C41—C42 | −17.2 (5) |
C4—N8—C7—N4 | −176.0 (3) | C40—C41—C42—C43 | 1.8 (5) |
C7—N4—C8—C9 | 100.0 (3) | N10—C41—C42—C43 | −179.2 (3) |
C17—N4—C8—C9 | −79.6 (3) | C41—C42—C43—C38 | −0.2 (5) |
C10—N3—C9—C8 | 91.6 (3) | N11—C38—C43—C42 | 180.0 (3) |
N4—C8—C9—N3 | 177.7 (2) | C39—C38—C43—C42 | −0.8 (4) |
C9—N3—C10—O3 | 0.3 (4) | C34—N13—C44—O13 | −179.1 (2) |
C9—N3—C10—N2 | −179.3 (2) | C35—N13—C44—O13 | 3.2 (4) |
C11—N2—C10—O3 | 6.3 (4) | C34—N13—C44—N17 | 0.5 (4) |
C11—N2—C10—N3 | −174.0 (2) | C35—N13—C44—N17 | −177.3 (2) |
C10—N2—C11—C12 | 2.1 (4) | C45—N17—C44—O13 | 4.7 (4) |
C10—N2—C11—C16 | −179.0 (2) | C45—N17—C44—N13 | −174.8 (2) |
N2—C11—C12—C13 | −179.0 (2) | C44—N17—C45—C50 | −177.8 (2) |
C16—C11—C12—C13 | 2.1 (4) | C44—N17—C45—C46 | 3.1 (4) |
C11—C12—C13—C14 | −0.3 (4) | C50—C45—C46—C47 | 0.9 (4) |
C12—C13—C14—C15 | −1.8 (4) | N17—C45—C46—C47 | −179.9 (2) |
C12—C13—C14—N1 | 175.4 (2) | C45—C46—C47—C48 | −1.6 (4) |
O2—N1—C14—C15 | 174.6 (3) | C46—C47—C48—C49 | 0.8 (4) |
O1—N1—C14—C15 | −2.7 (4) | C46—C47—C48—N18 | −179.3 (2) |
O2—N1—C14—C13 | −2.6 (4) | O14—N18—C48—C47 | −14.2 (4) |
O1—N1—C14—C13 | −179.9 (2) | O15—N18—C48—C47 | 165.5 (2) |
C13—C14—C15—C16 | 2.0 (4) | O14—N18—C48—C49 | 165.7 (3) |
N1—C14—C15—C16 | −175.2 (2) | O15—N18—C48—C49 | −14.6 (3) |
C14—C15—C16—C11 | −0.2 (4) | C47—C48—C49—C50 | 0.7 (4) |
N2—C11—C16—C15 | 179.2 (2) | N18—C48—C49—C50 | −179.3 (2) |
C12—C11—C16—C15 | −1.8 (4) | C48—C49—C50—C45 | −1.3 (4) |
C7—N4—C17—C18 | 81.5 (3) | C46—C45—C50—C49 | 0.6 (4) |
C8—N4—C17—C18 | −98.9 (3) | N17—C45—C50—C49 | −178.7 (2) |
C19—N5—C18—C17 | 75.3 (3) | C51—C52—C53—C54 | −56.8 (4) |
N4—C17—C18—N5 | −161.0 (2) | C63—N19—C54—C53 | −172.7 (2) |
C18—N5—C19—O7 | −5.2 (4) | C59—N19—C54—C53 | −52.7 (3) |
C18—N5—C19—N6 | 174.8 (2) | C55—N19—C54—C53 | 67.1 (3) |
C20—N6—C19—O7 | 12.1 (4) | C52—C53—C54—N19 | −167.5 (2) |
C20—N6—C19—N5 | −167.8 (3) | C54—N19—C55—C56 | 178.0 (2) |
C19—N6—C20—C21 | −22.3 (4) | C63—N19—C55—C56 | 58.9 (3) |
C19—N6—C20—C25 | 157.0 (3) | C59—N19—C55—C56 | −59.9 (3) |
N6—C20—C21—C22 | 177.5 (3) | N19—C55—C56—C57 | −173.0 (3) |
C25—C20—C21—C22 | −1.8 (4) | C55—C56—C57—C58 | −174.2 (3) |
C20—C21—C22—C23 | 1.2 (4) | C54—N19—C59—C60 | −56.1 (3) |
C21—C22—C23—C24 | 0.5 (4) | C63—N19—C59—C60 | 63.6 (3) |
C21—C22—C23—N7 | −178.2 (2) | C55—N19—C59—C60 | −176.7 (3) |
O8—N7—C23—C22 | −172.3 (3) | N19—C59—C60—C61 | −172.1 (3) |
O9—N7—C23—C22 | 7.3 (4) | C59—C60—C61—C62 | −179.5 (4) |
O8—N7—C23—C24 | 8.9 (4) | C54—N19—C63—C64 | −70.4 (3) |
O9—N7—C23—C24 | −171.4 (2) | C59—N19—C63—C64 | 167.8 (3) |
C22—C23—C24—C25 | −1.4 (4) | C55—N19—C63—C64 | 49.4 (3) |
N7—C23—C24—C25 | 177.3 (2) | N19—C63—C64—C65 | 172.0 (3) |
C23—C24—C25—C20 | 0.7 (4) | C63—C64—C65—C66 | 171.0 (3) |
N6—C20—C25—C24 | −178.4 (2) | C75—N20—C67—C68 | 52.6 (3) |
C21—C20—C25—C24 | 0.9 (4) | C71—N20—C67—C68 | 174.5 (3) |
O18—N16—C26—C27 | −8.2 (4) | C79—N20—C67—C68 | −66.5 (3) |
O17—N16—C26—C27 | 171.0 (3) | N20—C67—C68—C69 | 173.3 (3) |
O18—N16—C26—C31 | 173.4 (3) | C67—C68—C69—C70 | 171.4 (3) |
O17—N16—C26—C31 | −7.5 (5) | C75—N20—C71—C72 | 49.7 (3) |
C31—C26—C27—C28 | −0.4 (4) | C67—N20—C71—C72 | −71.0 (3) |
N16—C26—C27—C28 | −178.8 (3) | C79—N20—C71—C72 | 168.6 (3) |
C26—C27—C28—C29 | −0.7 (4) | N20—C71—C72—C73 | −153.1 (3) |
C32—N15—C29—C30 | 16.0 (4) | C71—C72—C73—C74 | 175.4 (3) |
C32—N15—C29—C28 | −162.8 (2) | C71—N20—C75—C76 | 51.1 (3) |
C27—C28—C29—C30 | 0.6 (4) | C67—N20—C75—C76 | 171.3 (2) |
C27—C28—C29—N15 | 179.6 (2) | C79—N20—C75—C76 | −68.1 (3) |
N15—C29—C30—C31 | −178.3 (3) | N20—C75—C76—C77 | −166.4 (3) |
C28—C29—C30—C31 | 0.5 (5) | C75—C76—C77—C78 | 74.3 (4) |
C27—C26—C31—C30 | 1.5 (5) | C75—N20—C79—C80A | −163.3 (6) |
N16—C26—C31—C30 | 179.9 (3) | C71—N20—C79—C80A | 75.7 (6) |
C29—C30—C31—C26 | −1.5 (5) | C67—N20—C79—C80A | −43.4 (6) |
C33—N14—C32—O16 | 3.9 (4) | C75—N20—C79—C80B | 172.4 (5) |
C33—N14—C32—N15 | −175.8 (2) | C71—N20—C79—C80B | 51.4 (5) |
C29—N15—C32—O16 | −6.2 (4) | C67—N20—C79—C80B | −67.8 (5) |
C29—N15—C32—N14 | 173.5 (2) | C80B—C79—C80A—C81A | −84.0 (13) |
C32—N14—C33—C34 | −75.5 (3) | N20—C79—C80A—C81A | −174.5 (5) |
C44—N13—C34—C33 | −81.5 (3) | C79—C80A—C81A—C82A | 53.5 (12) |
C35—N13—C34—C33 | 96.2 (3) | C80A—C79—C80B—C81B | 108.0 (17) |
N14—C33—C34—N13 | 164.1 (2) | N20—C79—C80B—C81B | −151.7 (6) |
C44—N13—C35—C36 | −87.5 (3) | C79—C80B—C81B—C82B | −46.3 (11) |
C34—N13—C35—C36 | 94.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N8—H8N···O7 | 0.90 (3) | 2.07 (3) | 2.955 (3) | 168 (3) |
N17—H17N···O16 | 0.90 (2) | 2.21 (2) | 3.100 (3) | 170 (2) |
N5—H5N···O21 | 0.90 (2) | 2.04 (2) | 2.915 (3) | 164 (3) |
N6—H6N···O22 | 0.90 (2) | 2.10 (2) | 2.986 (3) | 168 (2) |
N11—H11N···O19 | 0.90 (2) | 1.96 (2) | 2.854 (3) | 175 (2) |
N12—H12N···O22 | 0.90 (2) | 2.21 (2) | 3.058 (3) | 157 (3) |
O20—H20O···O24 | 0.93 (2) | 1.66 (2) | 2.583 (2) | 178 (3) |
O23—H23O···O22 | 0.93 (2) | 1.64 (2) | 2.568 (2) | 176 (2) |
O21—H21O···O19i | 0.93 (2) | 1.61 (2) | 2.528 (2) | 173 (3) |
O25—H25O···O26ii | 0.93 (2) | 1.59 (2) | 2.501 (2) | 166 (3) |
N2—H2N···O26i | 0.90 (2) | 2.08 (2) | 2.977 (3) | 174 (2) |
N3—H3N···O24i | 0.90 (2) | 2.09 (2) | 2.931 (3) | 155 (3) |
N14—H14N···O25ii | 0.90 (2) | 2.03 (2) | 2.930 (3) | 175 (2) |
N15—H15N···O24ii | 0.90 (2) | 2.10 (2) | 2.986 (3) | 168 (2) |
C3—H3···O4 | 0.95 | 2.17 | 2.789 (4) | 121 |
C5—H5···O7 | 0.95 | 2.53 | 3.279 (4) | 136 |
C12—H12···O3 | 0.95 | 2.23 | 2.844 (3) | 122 |
C21—H21···O7 | 0.95 | 2.31 | 2.872 (4) | 118 |
C30—H30···O16 | 0.95 | 2.32 | 2.903 (4) | 119 |
C43—H43···O12 | 0.95 | 2.32 | 2.910 (4) | 120 |
C46—H46···O13 | 0.95 | 2.19 | 2.810 (3) | 122 |
C18—H18A···O1iii | 0.99 | 2.42 | 3.345 (4) | 156 |
C30—H30···O6iv | 0.95 | 2.58 | 3.265 (4) | 129 |
C33—H33B···O11Aiii | 0.99 | 2.58 | 3.235 (12) | 123 |
C39—H39···O21i | 0.95 | 2.52 | 3.446 (3) | 164 |
C54—H54A···O15v | 0.99 | 2.46 | 3.447 (4) | 173 |
C63—H63A···O3 | 0.99 | 2.42 | 3.379 (4) | 164 |
C63—H63B···O4 | 0.99 | 2.26 | 3.003 (4) | 131 |
C64—H64B···O15v | 0.99 | 2.46 | 3.348 (4) | 149 |
C70—H70B···O10Aiii | 0.98 | 2.47 | 3.289 (6) | 141 |
C75—H75A···O13 | 0.99 | 2.31 | 3.158 (4) | 143 |
C75—H75B···O1vi | 0.99 | 2.58 | 3.514 (4) | 157 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+2, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+1, −z+1; (v) x−1, y, z−1; (vi) x+1, y, z+1. |
Acknowledgements
We are grateful to the Comprehensive Training Platform of Specialized Laboratory, College of Chemistry, Sichuan University, for the IR, NMR, HRMS and XRD analyses. We appreciate the help of Dr Yue Qi and Dr Meng Yang with the X-ray single-crystal measurements.
Funding information
Funding for this research was provided by: National Natural Science Foundation of China (grant No. 21501123).
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