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Puckering effects of 4-hydroxy-L-proline isomers on the conformation of ornithine-free Gramicidin S
aOsaka Medical and Pharmaceutical University, 4-20-1 Nasahara, Takatsuki, Osaka 590-1094, Japan
*Correspondence e-mail: mitsunobu.doi@ompu.ac.jp
The cyclic peptide cyclo(Val-Leu-Leu-D-Phe-Pro)2 (peptide 1) was specifically designed for structural chemistry investigations, drawing inspiration from Gramicidin S (GS). Previous studies have shown that Pro residues within 1 adopt a down-puckering conformation of the pyrrolidine ring. By incorporating fluoride-Pro with 4-trans/cis-isomers into 1, an up-puckering conformation was successfully induced. In the current investigation, introducing hydroxyprolines with 4-trans/cis-isomer configurations (tHyp/cHyp) into 1 gave cyclo(Val-Leu-Leu-D-Phe-tHyp)2 methanol disolvate monohydrate, C62H94N10O12·2CH4O·H2O (4), and cyclo(Val-Leu-Leu-D-Phe-cHyp)2 monohydrate, C62H94N10O12·H2O (5), respectively. However, the puckering of 4 and 5 remained in the down conformation, regardless of the geometric position of the hydroxyl group. Although the backbone structure of 4 with trans-substitution was asymmetric, the asymmetric backbone of 5 with cis-substitution was unexpected. It is speculated that the anticipated influence of stress from the geometric positioning, which was expected to affect the puckering, may have been mitigated by interactions between the hydroxyl groups of hydroxyproline, the solvent molecules, and peptides.
1. Chemical context
Gramicidin S (GS) is a cyclic decapeptide (Gause & Brazhnikova, 1944), forming intramolecular sheet and turn structures (Hodgkin & Oughton, 1957
; Schmidt et al., 1957
). Its chemical structure exhibits C2 symmetry, featuring a repeated sequence of Val-Orn-Leu-D-Phe-Pro (Balasubramanian, 1967
). Our focus has been on investigating cyclo(Val-Leu-Leu-D-Phe-Pro)2 (peptide 1), which mimics the structural characteristics of GS and facilitates structural analysis (Asano et al., 2019
, 2021
). This is achieved by substituting the Orn residue with Leu to reduce interactions with solvent molecules. In previous crystal structures of GS derivatives, the pyrrolidine ring of Pro consistently exhibited a down-puckering conformation (Doi et al., 2001
; Llamas-Saiz et al. 2007
; Asano & Doi, 2019
). To explore this further, we introduced a geometric isomer of 4-fluoride Pro into peptide 1, examining its impact on Pro puckering and structure (Asano et al., 2023
). Notably, derivative 2 containing 4-trans-fluoro-Pro (tFPro) displayed an up-puckering for the first time, while derivative 3 with 4-cis-fluoro-Pro (cFPro) retained the conventional down-puckering. In this study, we introduced 4-trans-hydroxyproline (tHyp) and 4-cis-hydroxyproline (cHyp) into peptide 1, resulting in derivatives 4 and 5, respectively. We compared their structures with fluoride-Pro derivatives.
2. Structural commentary
Fig. 1 illustrates the structures of 4 and 5, which have three intramolecular hydrogen bonds (Table 1
, Fig. 2
) [4: N31⋯O62 = 2.838 (5), N61⋯O32 = 3.048 (5) and N81⋯O12 = 2.905 (4) Å, 5: N11⋯O82 = 3.012 (2), N31⋯O62 = 2.985 (2) and N81⋯O12 = 2.831 (2) Å], forming a sheet structure. Additionally, two bends are observed (D-Phe-Pro moieties), one forming a β-turn of type II', while the other is not classed into any β-turn (Table 2
). Such asymmetrical structures arise from outward-facing carbonyl groups [O82 (4) and O32 (5)], preventing intramolecular hydrogen-bond formation (Fig. 2
). Comparing the peptide backbones, 2 and 4, with a 4-trans-substitution of Pro, exhibit similar structures with the asymmetric peptide backbone (Fig. 3
). Conversely, 3 and 5, with cis-substitution, display differences in backbone structure attributed to the asymmetric structure of 5.
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![]() | Figure 1 Molecular structures of 4 and 5. Hydrogen atoms are omitted for clarity. Oxygen atoms of solvent molecules are labeled. |
![]() | Figure 2 Backbone structures of 4 and 5. Dotted lines show intramolecular hydrogen bonds. |
![]() | Figure 3 Superimposition of backbone structures. The circled area highlights a region with noticeable drift in the backbone structures Molecular fittings were performed using ProFit (Martin, 2022 ![]() |
The puckering parameters (Table 3) reveal that both 4 and 5 exhibit Hyp in the down-puckering (Cβ-exo), which was somewhat unexpected. Table 4
outlines the puckering type and symmetry of the backbone structure. 1 and 3, with the pyrrolidine ring in the down-puckering mode, exhibit symmetric backbone structures (peptide 1 contains three independent molecules with coexisting structures), suggesting a preference for a symmetric backbone when the pyrrolidine ring is down-puckering. In contrast, peptide 2, with tFPro-induced up-puckering, displays an asymmetric backbone structure. Interestingly, in peptide 4 tHyp remains in the down-puckering form, indicating that the 4-trans-hydroxy group does not induce an up-puckering. Peptide 5, also down-puckered, shows an asymmetric backbone. No clear relationship between Hyp puckering and backbone structure was observed in 4 and 5.
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et al., 2010) shows significant differences of Δδ in Hα of 2 and 3 with fluoride-Pro (Asano et al., 2019
). In constrast, 4 and 5, containing Hyp, exhibit similar Δδ values to 1 (Fig. 4
), suggesting minimal influence on the peptide backbone. This could be attributed to the 4-position substitution of Hyp, where hydroxy groups (O54 and O104) form hydrogen bonds. While 4 and 5 form hydrogen bonds with solvent and neighboring molecules (Table 1
), no notable differences attributable to trans/cis are observed (Fig. 5
). As a hypothesis, compared to 2 and 3, the hydrogen bonds formed by the hydroxy groups of Hyp may reduce structural stresses from the trans/cis-geometry of Hyp, explaining the results of perturbation.
![]() | Figure 4 Plot of chemical shift perturbation (Δδ) of Hα atoms. The data of 1 are referenced from the previous report (Asano et al., 2019 ![]() |
![]() | Figure 5 Hydrogen-bond networks relating to Hyp residues. (a) tHyp5 and tHyp10 of 4. (b) cHyp5 and (c) cHyp10 of 5. |
3. Synthesis and crystallization
Petides 4 and 5 were synthesized using the conventional liquid-phase method (Izumiya et al., 1997). Crystals were grown from aqueous methanol solution. The NMR spectrum was measured in DMSO-d6 on a Varian Unity Inova 500 MHz. 1H NMR (p.p.m.): 4 δ 0.76 (d, J = 6.6 Hz,3H, Leu3-δ1CH33), 0.78 (d, J = 6.6 Hz, Val1-γ1CH3), 0.78 (d, J = 6.6 Hz,3H, Leu3-δ2CH33), 0.79 (d, J = 6.6 Hz, Val1-γ2CH3), 0.82 (d, J = 6.6 Hz, 3H, Leu2-δ1CH3), 0.82 (d, J = 6.6 Hz, 3H, Leu2-δ2CH3), 1.28 (m, J = 1.28 Hz, 1H, Leu2-βCH), 1.28 (m, 1H, Leu3-βCH), 1.41 (m, 1H, Leu3-β′CH), 1.41 (m, 1H, Leu3-γCH), 1.59 (non., J = 6.6 Hz, 1H, Leu2-γCH), 1.66 (m, 1H, tHyp5-βCH), 1.71 (m, J = 1.71 Hz, 1H, Leu2-β′CH), 2.03 (m, 2H, Val1-βCH), 2.04 (m, 1H, tHyp5-β′CH), 2.71 (dd, J = 9.9 Hz, 6.0 Hz, 1H, tHyp5-δCH), 2.83 (dd, J = 13.5 Hz, 7.2 Hz, 1H, D-Phe4-βCH), 2.90 (dd, J = 13.5 Hz, 7.2 Hz, 1H, D-Phe4-β′CH), 3.71 (dd, J = 9.9 Hz, 6.0 Hz, 1H, tHyp5-δ′CH), 4.13 (m, 1H, tHyp5-γCH), 4.30 (dd, J = 9.0 Hz, 6.6 Hz, 1H, Val1-αCH), 4.35 (dd, J = 8.4 Hz, 3.6 Hz, 1H, tHyp5-αCH), 4.44 (q, J = 8.4 Hz, 1H, Leu3-αCH), 4.45 (q, J = 7.2 Hz, 1H, D-Phe4-αCH), 4.58 (q, J = 7.8 Hz, 1H, Leu2-αCH), 5.12 (d, J = 3.6 Hz, 1H, tHyp5-γOH), 7.15 (br, 1H, Val1-CONH), 7.22 (m, 3H, D-Phe4-ArH), 7.28 (m, 2H, D-Phe4-ArH), 8.27 (d, J = 8.4 Hz, 1H, Leu3-CONH), 8.30 (d, J = 7.2 Hz, 1H, D-Phe4-CONH), 8.36 (d, J = 7.8 Hz, 1H, Leu2-CONH).
5 δ 0.77 (d, J = 6.6 Hz, 3H, Leu3-δ1CH3), 0.78 (d, J = 6.6 Hz, 3H, Val1-γ1CH3), 0.79 (d, J = 6.6 Hz, 3H, Val1-γ2CH3), 0.80 (d, J = 6.6 Hz, 3H, Leu3-δ2CH3), 0.85 (d, J = 6.6 Hz, 3H, Leu2-δ1CH3), 0.86 (d, J = 6.6 Hz, 3H, Leu2-δ2CH3), 1.28 (m, 1H, Leu2-βCH), 1.36 (m, 1H, Leu3-βCH), 1.48 (m, 1H, Leu3-β′CH), 1.48 (m, 1H, Leu3-γCH), 1.60 (m, 1H, Leu2-γCH), 1.80 (m, 1H, Leu2-β′CH), 1.86 (m, 1H, cHyp5-βCH), 1.94 (m, 1H, cHyp5-β′CH), 1.97 (m, 1H, Val1-βCH), 2.79 (dd, J = 12.9 Hz, 6.0 Hz, 1H, D-Phe4-βCH), 2.89 (dd, J = 12.9 Hz, 8.4 Hz, 1H, D-Phe4-β′CH), 3.01 (m, 1H, cHyp5-δCH), 3.34 (m, 1H, cHyp5-δ′CH), 3.92 (br, 1H, cHyp5-γCH), 4.28 (dd, J = 9.6 Hz, 1.8 Hz, 1H, cHyp5-αCH), 4.37 (dd, J = 9.0 Hz, 6.6 Hz, 1H, Val1-αCH), 4.44 (td, J = 9.0 Hz, 6.6 Hz, 1H, Leu3-αCH), 4.50 (td, J = 8.4 Hz, 6.0 Hz, 1H, D-Phe4-αCH), 4.62 (q, J = 8.4 Hz, 1H, Leu2-αCH), 4.96 (d, J = 2.4 Hz, 1H, cHyp5-γOH), 6.98 (d, J = 9.0 Hz, 1H, Val1-CONH), 7.22 (m, 3H, D-Phe4-ArH), 7.23 (m, 2H, D-Phe4-ArH), 7.95 (d, J = 6.0 Hz, 1H, D-Phe4-CONH), 8.36 (d, J = 9.0 Hz, 1H, Leu3-CONH), 8.50 (d, J = 8.4 Hz, 1H, Leu2-CONH).
4. Refinement
Crystal data, data collection and structure . All H atoms were located in difference maps and then treated as riding in geometrically idealized positions with constrained distances set to 0.93 Å (Csp2—H), 0.98 Å (R3—CH), 0.97 Å (R2—CH2), 0.96 Å (R—CH3), 082 Å (R—OH) and 0.86 Å (Nsp2—H). Uiso(H) parameters were set to values of either 1.2 or 1.5 (methyl and hydroxy groups) times Ueq of the attached atom. The H atoms attached to water (5) and the hydroxyl groups of Hyp (4 and 5) were located in the Fourier map considering donor–acceptor pairs in the hydrogen-bond network, and included in the calculation of structure factors with fixed position. The H atoms attached to methanol and water molecules of (4) were located in the Fourier map and included in the with restraints for the bond lengths and angles.
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Supporting information
https://doi.org/10.1107/S2056989024007771/jp2008sup1.cif
contains datablocks global, 4, 5. DOI:Structure factors: contains datablock 4. DOI: https://doi.org/10.1107/S2056989024007771/jp20084sup2.hkl
Structure factors: contains datablock 5. DOI: https://doi.org/10.1107/S2056989024007771/jp20085sup3.hkl
C62H94N10O12·2CH4O·H2O | Dx = 1.225 Mg m−3 |
Mr = 1253.57 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 27488 reflections |
a = 11.8909 (1) Å | θ = 2.8–70.2° |
b = 18.8562 (2) Å | µ = 0.71 mm−1 |
c = 30.3163 (3) Å | T = 100 K |
V = 6797.4 (1) Å3 | Needle, colourless |
Z = 4 | 0.45 × 0.16 × 0.10 mm |
F(000) = 2712 |
RIGAKU XtaLAB P200K diffractometer | 12349 independent reflections |
Radiation source: rotating anode | 11935 reflections with I > 2σ(I) |
Detector resolution: 5.8140 pixels mm-1 | Rint = 0.026 |
ω–scan | θmax = 68.3°, θmin = 2.9° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015) | h = −14→14 |
Tmin = 0.618, Tmax = 1.0 | k = −17→22 |
42425 measured reflections | l = −35→36 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.067 | w = 1/[σ2(Fo2) + (0.1438P)2 + 2.8253P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.203 | (Δ/σ)max = 0.011 |
S = 1.09 | Δρmax = 0.98 e Å−3 |
12349 reflections | Δρmin = −1.30 e Å−3 |
835 parameters | Absolute structure: Flack x determined using 5149 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
29 restraints | Absolute structure parameter: 0.08 (4) |
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) | |
N11 | 0.7511 (3) | 0.74028 (18) | 0.43846 (10) | 0.0302 (7) | |
H11 | 0.770195 | 0.696322 | 0.439474 | 0.036* | |
C11 | 0.7533 (3) | 0.7758 (2) | 0.39577 (12) | 0.0304 (8) | |
H11A | 0.727017 | 0.824775 | 0.399246 | 0.037* | |
C12 | 0.6729 (3) | 0.7356 (2) | 0.36512 (12) | 0.0277 (7) | |
O12 | 0.6704 (3) | 0.67041 (15) | 0.36572 (10) | 0.0356 (6) | |
C13 | 0.8739 (4) | 0.7762 (2) | 0.37671 (13) | 0.0347 (8) | |
H13 | 0.895444 | 0.727050 | 0.370346 | 0.042* | |
C14 | 0.9574 (5) | 0.8064 (4) | 0.40964 (18) | 0.0581 (14) | |
H14A | 0.953849 | 0.779726 | 0.436570 | 0.087* | |
H14B | 1.031958 | 0.803513 | 0.397628 | 0.087* | |
H14C | 0.939160 | 0.855093 | 0.415515 | 0.087* | |
C15 | 0.8788 (4) | 0.8180 (4) | 0.33395 (16) | 0.0528 (13) | |
H15A | 0.825827 | 0.798624 | 0.313307 | 0.079* | |
H15B | 0.860409 | 0.866711 | 0.339699 | 0.079* | |
H15C | 0.953207 | 0.815132 | 0.321812 | 0.079* | |
N21 | 0.6130 (3) | 0.77560 (17) | 0.33758 (11) | 0.0291 (7) | |
H21 | 0.620698 | 0.820899 | 0.338867 | 0.035* | |
C21 | 0.5345 (3) | 0.7459 (2) | 0.30511 (12) | 0.0311 (8) | |
H21A | 0.544977 | 0.694467 | 0.303064 | 0.037* | |
C22 | 0.5655 (4) | 0.7805 (2) | 0.26146 (13) | 0.0319 (8) | |
O22 | 0.5585 (3) | 0.84551 (15) | 0.25738 (9) | 0.0392 (7) | |
C23 | 0.4142 (4) | 0.7625 (2) | 0.31965 (14) | 0.0347 (8) | |
H23A | 0.405677 | 0.747000 | 0.349983 | 0.042* | |
H23B | 0.404608 | 0.813550 | 0.319307 | 0.042* | |
C24 | 0.3186 (4) | 0.7296 (3) | 0.29258 (18) | 0.0519 (12) | |
H24 | 0.327963 | 0.678135 | 0.295158 | 0.062* | |
C25 | 0.3136 (6) | 0.7446 (4) | 0.2449 (2) | 0.0689 (17) | |
H25A | 0.384700 | 0.733302 | 0.231625 | 0.103* | |
H25B | 0.255624 | 0.716374 | 0.231613 | 0.103* | |
H25C | 0.297362 | 0.793960 | 0.240403 | 0.103* | |
C26 | 0.2075 (4) | 0.7467 (4) | 0.3152 (2) | 0.0567 (13) | |
H26A | 0.213421 | 0.736402 | 0.346154 | 0.085* | |
H26B | 0.190369 | 0.796084 | 0.311307 | 0.085* | |
H26C | 0.148631 | 0.718498 | 0.302517 | 0.085* | |
N31 | 0.6051 (3) | 0.73732 (18) | 0.22955 (11) | 0.0326 (7) | |
H31 | 0.608008 | 0.692423 | 0.234401 | 0.039* | |
C31 | 0.6433 (4) | 0.7647 (2) | 0.18698 (13) | 0.0336 (8) | |
H31A | 0.633395 | 0.816270 | 0.186285 | 0.040* | |
C32 | 0.5716 (4) | 0.7308 (2) | 0.15055 (12) | 0.0325 (8) | |
O32 | 0.5943 (3) | 0.67093 (15) | 0.13636 (9) | 0.0362 (6) | |
C33 | 0.7670 (4) | 0.7467 (3) | 0.17898 (15) | 0.0431 (10) | |
H33A | 0.774911 | 0.695502 | 0.178268 | 0.052* | |
H33B | 0.788401 | 0.764618 | 0.150195 | 0.052* | |
C34 | 0.8490 (4) | 0.7765 (3) | 0.21344 (17) | 0.0487 (11) | |
H34 | 0.830609 | 0.754519 | 0.241837 | 0.058* | |
C35 | 0.8372 (6) | 0.8560 (3) | 0.2189 (2) | 0.0605 (15) | |
H35A | 0.760630 | 0.867353 | 0.226147 | 0.091* | |
H35B | 0.885710 | 0.871854 | 0.242249 | 0.091* | |
H35C | 0.857672 | 0.879200 | 0.191929 | 0.091* | |
C36 | 0.9683 (6) | 0.7559 (4) | 0.2020 (3) | 0.0719 (18) | |
H36A | 0.973086 | 0.705394 | 0.198788 | 0.108* | |
H36B | 0.989868 | 0.778367 | 0.174902 | 0.108* | |
H36C | 1.017906 | 0.771021 | 0.225222 | 0.108* | |
N41 | 0.4847 (3) | 0.76819 (18) | 0.13525 (11) | 0.0358 (7) | |
H41 | 0.469741 | 0.809393 | 0.145909 | 0.043* | |
C41 | 0.4153 (4) | 0.7382 (2) | 0.10018 (13) | 0.0349 (9) | |
H41A | 0.461268 | 0.731981 | 0.073628 | 0.042* | |
C42 | 0.3692 (4) | 0.6662 (2) | 0.11459 (14) | 0.0347 (9) | |
O42 | 0.3136 (3) | 0.66123 (17) | 0.14827 (10) | 0.0418 (7) | |
C43 | 0.3166 (5) | 0.7876 (2) | 0.08969 (16) | 0.0437 (10) | |
H43A | 0.267756 | 0.791326 | 0.115191 | 0.052* | |
H43B | 0.344667 | 0.834569 | 0.082723 | 0.052* | |
C44 | 0.2511 (4) | 0.7585 (2) | 0.05083 (15) | 0.0373 (9) | |
C45 | 0.1610 (5) | 0.7130 (3) | 0.0566 (2) | 0.0599 (15) | |
H45 | 0.136209 | 0.702328 | 0.084932 | 0.072* | |
C46 | 0.1072 (6) | 0.6832 (3) | 0.0204 (3) | 0.074 (2) | |
H46 | 0.047616 | 0.651954 | 0.024686 | 0.089* | |
C47 | 0.1409 (6) | 0.6992 (3) | −0.0216 (2) | 0.0677 (18) | |
H47 | 0.104542 | 0.679259 | −0.045772 | 0.081* | |
C48 | 0.2280 (5) | 0.7446 (4) | −0.0275 (2) | 0.0676 (17) | |
H48 | 0.250581 | 0.756320 | −0.055994 | 0.081* | |
C49 | 0.2840 (4) | 0.7740 (3) | 0.00839 (18) | 0.0515 (12) | |
H49 | 0.344388 | 0.804442 | 0.003661 | 0.062* | |
N51 | 0.3898 (3) | 0.61001 (19) | 0.08838 (12) | 0.0376 (8) | |
C51 | 0.3384 (5) | 0.5413 (2) | 0.09743 (17) | 0.0466 (12) | |
H51 | 0.260115 | 0.548211 | 0.106586 | 0.056* | |
C52 | 0.4006 (4) | 0.4963 (2) | 0.13229 (15) | 0.0372 (9) | |
O52 | 0.3694 (3) | 0.43453 (16) | 0.13855 (11) | 0.0439 (7) | |
C53 | 0.3413 (6) | 0.5063 (3) | 0.0515 (2) | 0.0655 (19) | |
H53A | 0.277608 | 0.521094 | 0.033723 | 0.079* | |
H53B | 0.341028 | 0.454963 | 0.053849 | 0.079* | |
C54 | 0.4513 (7) | 0.5328 (3) | 0.03184 (17) | 0.0633 (18) | |
H54A | 0.514654 | 0.506975 | 0.044871 | 0.076* | |
C55 | 0.4539 (5) | 0.6105 (3) | 0.04670 (14) | 0.0471 (11) | |
H55A | 0.530541 | 0.626446 | 0.051475 | 0.057* | |
H55B | 0.418451 | 0.641031 | 0.025023 | 0.057* | |
O54 | 0.4519 (6) | 0.5242 (3) | −0.01478 (13) | 0.0907 (19) | |
H54 | 0.447565 | 0.563198 | −0.026631 | 0.136* | |
N61 | 0.4835 (3) | 0.52818 (18) | 0.15465 (11) | 0.0343 (7) | |
H61 | 0.497931 | 0.572021 | 0.149251 | 0.041* | |
C61 | 0.5502 (4) | 0.4912 (2) | 0.18787 (13) | 0.0328 (8) | |
H61A | 0.523587 | 0.442168 | 0.190241 | 0.039* | |
C62 | 0.5362 (4) | 0.5279 (2) | 0.23276 (13) | 0.0325 (8) | |
O62 | 0.5664 (3) | 0.58954 (16) | 0.23884 (10) | 0.0428 (7) | |
C63 | 0.6751 (4) | 0.4907 (2) | 0.17533 (13) | 0.0352 (9) | |
H63 | 0.700105 | 0.539978 | 0.172186 | 0.042* | |
C64 | 0.6915 (4) | 0.4534 (2) | 0.13108 (14) | 0.0408 (10) | |
H64A | 0.646433 | 0.476384 | 0.109026 | 0.061* | |
H64B | 0.769302 | 0.455817 | 0.122730 | 0.061* | |
H64C | 0.669128 | 0.404709 | 0.133670 | 0.061* | |
C65 | 0.7458 (4) | 0.4557 (3) | 0.21156 (15) | 0.0430 (10) | |
H65A | 0.733900 | 0.480106 | 0.238964 | 0.064* | |
H65B | 0.723724 | 0.406982 | 0.214685 | 0.064* | |
H65C | 0.823898 | 0.458091 | 0.203744 | 0.064* | |
N71 | 0.4937 (3) | 0.48684 (17) | 0.26479 (11) | 0.0325 (7) | |
H71 | 0.467375 | 0.445760 | 0.258034 | 0.039* | |
C71 | 0.4906 (4) | 0.5099 (2) | 0.31112 (13) | 0.0341 (9) | |
H71A | 0.496598 | 0.561724 | 0.312559 | 0.041* | |
C72 | 0.5925 (4) | 0.4763 (2) | 0.33371 (13) | 0.0345 (9) | |
O72 | 0.5959 (3) | 0.41255 (15) | 0.34212 (11) | 0.0410 (7) | |
C73 | 0.3817 (4) | 0.4860 (2) | 0.33336 (14) | 0.0370 (9) | |
H73A | 0.373229 | 0.435367 | 0.329003 | 0.044* | |
H73B | 0.319000 | 0.509217 | 0.318853 | 0.044* | |
C74 | 0.3753 (5) | 0.5018 (2) | 0.38287 (14) | 0.0419 (10) | |
H74 | 0.442177 | 0.480912 | 0.396632 | 0.050* | |
C75 | 0.3773 (5) | 0.5818 (3) | 0.39270 (16) | 0.0505 (12) | |
H75A | 0.442731 | 0.602718 | 0.379480 | 0.076* | |
H75B | 0.310938 | 0.603580 | 0.380723 | 0.076* | |
H75C | 0.379298 | 0.589191 | 0.424024 | 0.076* | |
C76 | 0.2738 (6) | 0.4663 (3) | 0.40298 (18) | 0.0594 (14) | |
H76A | 0.270933 | 0.476616 | 0.433963 | 0.089* | |
H76B | 0.206822 | 0.483728 | 0.388996 | 0.089* | |
H76C | 0.278949 | 0.415929 | 0.398759 | 0.089* | |
N81 | 0.6768 (3) | 0.52060 (18) | 0.34352 (12) | 0.0350 (7) | |
H81 | 0.671795 | 0.564481 | 0.336048 | 0.042* | |
C81 | 0.7769 (4) | 0.4959 (2) | 0.36664 (15) | 0.0385 (9) | |
H81A | 0.796621 | 0.448728 | 0.355463 | 0.046* | |
C82 | 0.7559 (5) | 0.4904 (2) | 0.41640 (16) | 0.0439 (10) | |
O82 | 0.8070 (5) | 0.4471 (2) | 0.43878 (13) | 0.0692 (13) | |
C83 | 0.8767 (4) | 0.5462 (2) | 0.35831 (16) | 0.0439 (10) | |
H83A | 0.939835 | 0.530673 | 0.376124 | 0.053* | |
H83B | 0.855992 | 0.593370 | 0.368221 | 0.053* | |
C84 | 0.9147 (5) | 0.5508 (3) | 0.31051 (18) | 0.0526 (12) | |
H84 | 0.847292 | 0.563022 | 0.293501 | 0.063* | |
C85 | 0.9526 (7) | 0.4796 (4) | 0.2934 (3) | 0.047 (2) | 0.645 (14) |
H85A | 0.895937 | 0.444747 | 0.299512 | 0.070* | 0.645 (14) |
H85B | 0.964521 | 0.482527 | 0.262120 | 0.070* | 0.645 (14) |
H85C | 1.021559 | 0.466328 | 0.307639 | 0.070* | 0.645 (14) |
C86 | 0.9937 (9) | 0.6087 (6) | 0.3032 (4) | 0.065 (3) | 0.645 (14) |
H86A | 0.963114 | 0.651767 | 0.315064 | 0.098* | 0.645 (14) |
H86B | 1.063520 | 0.598053 | 0.317685 | 0.098* | 0.645 (14) |
H86C | 1.006483 | 0.614253 | 0.272166 | 0.098* | 0.645 (14) |
C85' | 0.8673 (13) | 0.6032 (7) | 0.2834 (4) | 0.055 (4) | 0.355 (14) |
H85D | 0.898976 | 0.599805 | 0.254358 | 0.082* | 0.355 (14) |
H85E | 0.787422 | 0.596470 | 0.281839 | 0.082* | 0.355 (14) |
H85F | 0.883246 | 0.649177 | 0.295503 | 0.082* | 0.355 (14) |
C86' | 1.0482 (11) | 0.5716 (13) | 0.3153 (6) | 0.094 (8) | 0.355 (14) |
H86D | 1.085100 | 0.537293 | 0.333707 | 0.141* | 0.355 (14) |
H86E | 1.082614 | 0.571927 | 0.286707 | 0.141* | 0.355 (14) |
H86F | 1.054842 | 0.617770 | 0.328448 | 0.141* | 0.355 (14) |
N91 | 0.6846 (4) | 0.53721 (19) | 0.43392 (12) | 0.0392 (8) | |
H91 | 0.652936 | 0.568062 | 0.417132 | 0.047* | |
C91 | 0.6593 (4) | 0.5371 (2) | 0.48114 (14) | 0.0392 (9) | |
H91A | 0.725601 | 0.519874 | 0.497087 | 0.047* | |
C92 | 0.6395 (4) | 0.6144 (2) | 0.49370 (13) | 0.0345 (9) | |
O92 | 0.5478 (3) | 0.64221 (18) | 0.48768 (12) | 0.0445 (7) | |
C93 | 0.5593 (5) | 0.4893 (3) | 0.49263 (16) | 0.0487 (12) | |
H93A | 0.489674 | 0.513451 | 0.485393 | 0.058* | |
H93B | 0.562995 | 0.446141 | 0.475239 | 0.058* | |
C94 | 0.5600 (4) | 0.4707 (2) | 0.54107 (16) | 0.0438 (11) | |
C95 | 0.6451 (5) | 0.4265 (3) | 0.55792 (16) | 0.0469 (11) | |
H95 | 0.702407 | 0.410892 | 0.539459 | 0.056* | |
C96 | 0.6441 (5) | 0.4061 (3) | 0.60210 (17) | 0.0532 (13) | |
H96 | 0.700168 | 0.376530 | 0.613024 | 0.064* | |
C97 | 0.5605 (5) | 0.4296 (3) | 0.62927 (17) | 0.0535 (13) | |
H97 | 0.558991 | 0.415040 | 0.658574 | 0.064* | |
C98 | 0.4784 (5) | 0.4746 (3) | 0.61374 (19) | 0.0574 (13) | |
H98 | 0.423205 | 0.491461 | 0.632779 | 0.069* | |
C99 | 0.4778 (5) | 0.4950 (3) | 0.56943 (18) | 0.0507 (12) | |
H99 | 0.421841 | 0.525040 | 0.559008 | 0.061* | |
N101 | 0.7299 (3) | 0.65021 (18) | 0.50826 (11) | 0.0305 (7) | |
C101 | 0.7206 (4) | 0.7262 (2) | 0.51769 (13) | 0.0313 (8) | |
H101 | 0.651237 | 0.735061 | 0.534236 | 0.038* | |
C102 | 0.7212 (3) | 0.7720 (2) | 0.47610 (13) | 0.0305 (8) | |
O102 | 0.6959 (3) | 0.83529 (16) | 0.47898 (10) | 0.0434 (7) | |
C103 | 0.8221 (4) | 0.7408 (2) | 0.54753 (14) | 0.0394 (9) | |
H10A | 0.848867 | 0.789052 | 0.543741 | 0.047* | |
H10B | 0.802988 | 0.733490 | 0.578295 | 0.047* | |
C104 | 0.9107 (4) | 0.6873 (2) | 0.53232 (14) | 0.0366 (9) | |
H104 | 0.951983 | 0.705914 | 0.506848 | 0.044* | |
C105 | 0.8423 (4) | 0.6221 (2) | 0.51895 (15) | 0.0376 (9) | |
H10C | 0.875455 | 0.598960 | 0.493510 | 0.045* | |
H10D | 0.838119 | 0.588309 | 0.543027 | 0.045* | |
O104 | 0.9860 (3) | 0.6724 (2) | 0.56743 (11) | 0.0477 (8) | |
H10E | 1.049697 | 0.667366 | 0.557602 | 0.072* | |
O1M | 0.1547 (3) | 0.5876 (2) | 0.20060 (12) | 0.0569 (9) | |
H1M | 0.191779 | 0.609604 | 0.182352 | 0.085* | |
C1M | 0.2259 (7) | 0.5417 (5) | 0.2245 (3) | 0.086 (3) | |
H1M1 | 0.273266 | 0.569033 | 0.243693 | 0.130* | |
H1M2 | 0.271732 | 0.515138 | 0.204323 | 0.130* | |
H1M3 | 0.181168 | 0.509626 | 0.241746 | 0.130* | |
O1W | 0.4313 (5) | 0.3882 (2) | −0.05479 (14) | 0.0692 (12) | |
H1W | 0.392 (7) | 0.371 (4) | −0.032 (2) | 0.104* | |
H2W | 0.450 (8) | 0.430 (3) | −0.046 (3) | 0.104* | |
O2M | 0.5246 (6) | 0.6493 (3) | −0.0496 (3) | 0.228 (7) | |
H2MA | 0.578 (5) | 0.622 (4) | −0.041 (3) | 0.342* | |
C2M | 0.4742 (16) | 0.6599 (11) | −0.0908 (5) | 0.180 (7) | |
H2M1 | 0.459625 | 0.709557 | −0.094945 | 0.269* | |
H2M2 | 0.404764 | 0.634091 | −0.092165 | 0.269* | |
H2M3 | 0.523832 | 0.643424 | −0.113595 | 0.269* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0426 (17) | 0.0241 (16) | 0.0240 (15) | 0.0027 (13) | −0.0018 (13) | 0.0007 (12) |
C11 | 0.042 (2) | 0.0244 (19) | 0.0246 (18) | 0.0025 (15) | −0.0047 (15) | 0.0004 (14) |
C12 | 0.0375 (18) | 0.0214 (18) | 0.0244 (17) | 0.0016 (14) | 0.0009 (14) | −0.0013 (13) |
O12 | 0.0504 (16) | 0.0219 (14) | 0.0346 (14) | 0.0025 (12) | −0.0073 (12) | 0.0015 (11) |
C13 | 0.042 (2) | 0.032 (2) | 0.0302 (19) | 0.0000 (17) | −0.0027 (16) | 0.0014 (15) |
C14 | 0.052 (3) | 0.082 (4) | 0.040 (3) | −0.020 (3) | −0.008 (2) | 0.009 (3) |
C15 | 0.044 (2) | 0.081 (4) | 0.034 (2) | −0.006 (2) | −0.0015 (19) | 0.012 (2) |
N21 | 0.0426 (17) | 0.0180 (14) | 0.0268 (15) | −0.0015 (13) | −0.0038 (13) | −0.0011 (12) |
C21 | 0.043 (2) | 0.0232 (18) | 0.0270 (18) | −0.0008 (15) | −0.0060 (15) | −0.0040 (15) |
C22 | 0.045 (2) | 0.024 (2) | 0.0268 (18) | 0.0035 (16) | −0.0063 (16) | −0.0014 (15) |
O22 | 0.069 (2) | 0.0182 (14) | 0.0309 (14) | 0.0048 (13) | −0.0030 (13) | −0.0009 (11) |
C23 | 0.043 (2) | 0.030 (2) | 0.0319 (19) | −0.0010 (16) | −0.0040 (16) | −0.0032 (15) |
C24 | 0.045 (2) | 0.065 (3) | 0.046 (3) | −0.009 (2) | −0.006 (2) | −0.014 (2) |
C25 | 0.068 (4) | 0.078 (5) | 0.062 (4) | −0.001 (3) | −0.009 (3) | −0.015 (3) |
C26 | 0.046 (3) | 0.071 (4) | 0.053 (3) | −0.012 (2) | −0.003 (2) | −0.008 (3) |
N31 | 0.0506 (19) | 0.0207 (15) | 0.0266 (16) | 0.0034 (13) | −0.0054 (14) | −0.0007 (12) |
C31 | 0.051 (2) | 0.0238 (19) | 0.0258 (18) | −0.0001 (16) | −0.0056 (17) | −0.0012 (14) |
C32 | 0.052 (2) | 0.0229 (18) | 0.0227 (17) | 0.0001 (16) | −0.0022 (16) | −0.0006 (14) |
O32 | 0.0505 (16) | 0.0271 (14) | 0.0311 (13) | 0.0053 (12) | −0.0046 (12) | −0.0060 (11) |
C33 | 0.057 (3) | 0.040 (2) | 0.032 (2) | 0.000 (2) | −0.0020 (19) | −0.0063 (18) |
C34 | 0.055 (3) | 0.047 (3) | 0.044 (2) | 0.002 (2) | −0.013 (2) | −0.005 (2) |
C35 | 0.070 (3) | 0.050 (3) | 0.061 (3) | −0.004 (3) | −0.025 (3) | −0.010 (2) |
C36 | 0.068 (4) | 0.068 (4) | 0.080 (4) | 0.002 (3) | −0.023 (3) | −0.014 (3) |
N41 | 0.054 (2) | 0.0233 (16) | 0.0300 (16) | 0.0039 (15) | −0.0064 (15) | −0.0065 (13) |
C41 | 0.050 (2) | 0.026 (2) | 0.0287 (19) | 0.0030 (17) | −0.0061 (16) | 0.0012 (15) |
C42 | 0.046 (2) | 0.026 (2) | 0.033 (2) | 0.0050 (16) | −0.0100 (17) | −0.0034 (15) |
O42 | 0.0553 (18) | 0.0344 (16) | 0.0358 (16) | −0.0016 (14) | 0.0008 (14) | −0.0010 (12) |
C43 | 0.060 (3) | 0.028 (2) | 0.043 (2) | 0.0069 (19) | −0.011 (2) | −0.0025 (17) |
C44 | 0.046 (2) | 0.0238 (19) | 0.042 (2) | 0.0040 (16) | −0.0092 (18) | 0.0040 (16) |
C45 | 0.058 (3) | 0.053 (3) | 0.069 (3) | −0.015 (2) | −0.013 (3) | 0.030 (3) |
C46 | 0.078 (4) | 0.040 (3) | 0.103 (5) | −0.020 (3) | −0.048 (4) | 0.025 (3) |
C47 | 0.081 (4) | 0.046 (3) | 0.077 (4) | 0.011 (3) | −0.047 (4) | −0.014 (3) |
C48 | 0.063 (3) | 0.098 (5) | 0.042 (3) | 0.012 (3) | −0.013 (2) | −0.007 (3) |
C49 | 0.051 (3) | 0.061 (3) | 0.043 (3) | −0.008 (2) | −0.011 (2) | 0.015 (2) |
N51 | 0.056 (2) | 0.0243 (17) | 0.0323 (17) | 0.0045 (15) | −0.0109 (15) | −0.0048 (14) |
C51 | 0.063 (3) | 0.027 (2) | 0.050 (3) | 0.002 (2) | −0.025 (2) | −0.0061 (19) |
C52 | 0.050 (2) | 0.024 (2) | 0.037 (2) | 0.0029 (17) | −0.0067 (18) | −0.0066 (16) |
O52 | 0.0610 (19) | 0.0221 (15) | 0.0485 (17) | −0.0033 (13) | −0.0129 (15) | −0.0027 (12) |
C53 | 0.109 (5) | 0.031 (2) | 0.057 (3) | 0.013 (3) | −0.049 (3) | −0.015 (2) |
C54 | 0.116 (5) | 0.038 (3) | 0.036 (2) | 0.030 (3) | −0.029 (3) | −0.020 (2) |
C55 | 0.073 (3) | 0.039 (3) | 0.030 (2) | 0.014 (2) | −0.006 (2) | −0.0089 (18) |
O54 | 0.167 (5) | 0.067 (3) | 0.038 (2) | 0.039 (3) | −0.034 (3) | −0.0287 (19) |
N61 | 0.050 (2) | 0.0212 (16) | 0.0314 (17) | −0.0011 (14) | −0.0078 (15) | −0.0018 (13) |
C61 | 0.050 (2) | 0.0215 (18) | 0.0265 (18) | −0.0017 (16) | −0.0055 (17) | 0.0002 (14) |
C62 | 0.045 (2) | 0.0219 (19) | 0.0307 (19) | −0.0004 (15) | −0.0020 (16) | −0.0014 (15) |
O62 | 0.072 (2) | 0.0244 (15) | 0.0324 (15) | −0.0064 (14) | 0.0010 (14) | −0.0036 (11) |
C63 | 0.051 (2) | 0.0250 (19) | 0.0292 (19) | −0.0003 (17) | −0.0016 (17) | −0.0025 (15) |
C64 | 0.058 (3) | 0.032 (2) | 0.032 (2) | −0.0028 (19) | 0.0043 (18) | −0.0070 (17) |
C65 | 0.054 (3) | 0.037 (2) | 0.038 (2) | 0.006 (2) | −0.007 (2) | −0.0021 (18) |
N71 | 0.0511 (19) | 0.0186 (15) | 0.0277 (16) | −0.0014 (13) | −0.0014 (14) | −0.0014 (12) |
C71 | 0.056 (2) | 0.0192 (18) | 0.0270 (19) | 0.0012 (16) | −0.0039 (17) | −0.0025 (14) |
C72 | 0.054 (2) | 0.0245 (19) | 0.0250 (17) | −0.0018 (17) | −0.0003 (17) | −0.0030 (14) |
O72 | 0.0616 (19) | 0.0170 (14) | 0.0445 (16) | −0.0011 (12) | −0.0110 (14) | 0.0037 (11) |
C73 | 0.051 (2) | 0.029 (2) | 0.031 (2) | −0.0003 (17) | 0.0000 (17) | −0.0017 (16) |
C74 | 0.063 (3) | 0.033 (2) | 0.029 (2) | 0.003 (2) | 0.0019 (19) | −0.0007 (16) |
C75 | 0.077 (3) | 0.038 (3) | 0.037 (2) | 0.009 (2) | 0.006 (2) | −0.0078 (19) |
C76 | 0.082 (4) | 0.056 (3) | 0.040 (3) | −0.002 (3) | 0.016 (3) | 0.002 (2) |
N81 | 0.0492 (19) | 0.0203 (16) | 0.0354 (17) | 0.0005 (14) | −0.0022 (15) | −0.0006 (13) |
C81 | 0.053 (2) | 0.0214 (19) | 0.041 (2) | 0.0009 (17) | −0.0061 (19) | −0.0034 (16) |
C82 | 0.064 (3) | 0.025 (2) | 0.042 (2) | −0.0007 (19) | −0.010 (2) | −0.0006 (18) |
O82 | 0.126 (4) | 0.0357 (19) | 0.046 (2) | 0.027 (2) | −0.014 (2) | 0.0070 (16) |
C83 | 0.051 (2) | 0.031 (2) | 0.050 (3) | 0.0001 (19) | 0.000 (2) | −0.0081 (18) |
C84 | 0.069 (3) | 0.036 (2) | 0.052 (3) | 0.005 (2) | 0.007 (3) | −0.006 (2) |
C85 | 0.045 (4) | 0.046 (4) | 0.050 (4) | 0.014 (3) | −0.003 (3) | −0.010 (3) |
C86 | 0.062 (6) | 0.054 (6) | 0.079 (7) | −0.016 (5) | 0.033 (5) | −0.019 (5) |
C85' | 0.084 (11) | 0.039 (8) | 0.041 (7) | 0.006 (7) | 0.006 (7) | 0.002 (6) |
C86' | 0.13 (2) | 0.069 (14) | 0.080 (14) | 0.028 (15) | 0.025 (14) | 0.023 (11) |
N91 | 0.059 (2) | 0.0304 (18) | 0.0287 (17) | −0.0014 (16) | −0.0072 (16) | −0.0002 (14) |
C91 | 0.053 (2) | 0.035 (2) | 0.030 (2) | −0.0077 (19) | −0.0081 (18) | 0.0026 (16) |
C92 | 0.041 (2) | 0.039 (2) | 0.0241 (17) | −0.0042 (17) | −0.0020 (15) | 0.0027 (16) |
O92 | 0.0416 (17) | 0.0433 (18) | 0.0484 (18) | −0.0013 (13) | −0.0074 (14) | −0.0005 (14) |
C93 | 0.067 (3) | 0.040 (3) | 0.039 (2) | −0.015 (2) | −0.011 (2) | 0.004 (2) |
C94 | 0.060 (3) | 0.032 (2) | 0.040 (2) | −0.014 (2) | −0.012 (2) | 0.0049 (18) |
C95 | 0.064 (3) | 0.038 (2) | 0.038 (2) | −0.007 (2) | −0.007 (2) | 0.0040 (19) |
C96 | 0.072 (3) | 0.044 (3) | 0.044 (3) | −0.012 (2) | −0.013 (2) | 0.011 (2) |
C97 | 0.073 (3) | 0.048 (3) | 0.039 (2) | −0.015 (3) | −0.004 (2) | 0.009 (2) |
C98 | 0.068 (3) | 0.055 (3) | 0.050 (3) | −0.014 (3) | 0.005 (3) | 0.000 (2) |
C99 | 0.061 (3) | 0.038 (3) | 0.053 (3) | −0.007 (2) | −0.005 (2) | 0.008 (2) |
N101 | 0.0384 (17) | 0.0260 (17) | 0.0270 (15) | 0.0007 (13) | −0.0027 (13) | 0.0006 (12) |
C101 | 0.043 (2) | 0.0246 (19) | 0.0265 (18) | 0.0016 (15) | 0.0006 (15) | 0.0010 (14) |
C102 | 0.041 (2) | 0.0241 (19) | 0.0259 (18) | 0.0001 (15) | 0.0002 (15) | 0.0001 (14) |
O102 | 0.070 (2) | 0.0264 (15) | 0.0336 (15) | 0.0071 (14) | 0.0053 (14) | −0.0031 (12) |
C103 | 0.056 (3) | 0.036 (2) | 0.0258 (19) | −0.0042 (19) | −0.0039 (17) | −0.0008 (16) |
C104 | 0.046 (2) | 0.036 (2) | 0.0281 (18) | −0.0054 (17) | −0.0072 (17) | 0.0022 (16) |
C105 | 0.046 (2) | 0.031 (2) | 0.036 (2) | 0.0007 (17) | −0.0071 (18) | 0.0025 (16) |
O104 | 0.0499 (18) | 0.050 (2) | 0.0432 (17) | −0.0073 (15) | −0.0152 (15) | 0.0111 (15) |
O1M | 0.061 (2) | 0.067 (3) | 0.0432 (19) | −0.0003 (19) | −0.0035 (16) | 0.0120 (17) |
C1M | 0.077 (4) | 0.115 (6) | 0.067 (4) | 0.032 (4) | 0.024 (3) | 0.041 (4) |
O1W | 0.117 (4) | 0.042 (2) | 0.049 (2) | −0.008 (2) | 0.006 (2) | 0.0042 (17) |
O2M | 0.156 (9) | 0.38 (2) | 0.144 (9) | 0.047 (12) | 0.009 (7) | 0.065 (11) |
C2M | 0.178 (13) | 0.209 (16) | 0.152 (12) | 0.029 (12) | −0.047 (10) | 0.069 (12) |
N11—C102 | 1.336 (5) | C63—H63 | 0.9800 |
N11—C11 | 1.458 (5) | C64—H64A | 0.9600 |
N11—H11 | 0.8600 | C64—H64B | 0.9600 |
C11—C12 | 1.533 (5) | C64—H64C | 0.9600 |
C11—C13 | 1.546 (6) | C65—H65A | 0.9600 |
C11—H11A | 0.9800 | C65—H65B | 0.9600 |
C12—O12 | 1.231 (5) | C65—H65C | 0.9600 |
C12—N21 | 1.331 (5) | N71—C71 | 1.471 (5) |
C13—C15 | 1.519 (6) | N71—H71 | 0.8600 |
C13—C14 | 1.519 (7) | C71—C72 | 1.529 (6) |
C13—H13 | 0.9800 | C71—C73 | 1.528 (6) |
C14—H14A | 0.9600 | C71—H71A | 0.9800 |
C14—H14B | 0.9600 | C72—O72 | 1.230 (5) |
C14—H14C | 0.9600 | C72—N81 | 1.338 (6) |
C15—H15A | 0.9600 | C73—C74 | 1.532 (6) |
C15—H15B | 0.9600 | C73—H73A | 0.9700 |
C15—H15C | 0.9600 | C73—H73B | 0.9700 |
N21—C21 | 1.468 (5) | C74—C76 | 1.509 (8) |
N21—H21 | 0.8600 | C74—C75 | 1.539 (7) |
C21—C22 | 1.521 (5) | C74—H74 | 0.9800 |
C21—C23 | 1.530 (6) | C75—H75A | 0.9600 |
C21—H21A | 0.9800 | C75—H75B | 0.9600 |
C22—O22 | 1.234 (5) | C75—H75C | 0.9600 |
C22—N31 | 1.350 (5) | C76—H76A | 0.9600 |
C23—C24 | 1.533 (6) | C76—H76B | 0.9600 |
C23—H23A | 0.9700 | C76—H76C | 0.9600 |
C23—H23B | 0.9700 | N81—C81 | 1.458 (6) |
C24—C25 | 1.474 (9) | N81—H81 | 0.8600 |
C24—C26 | 1.523 (8) | C81—C82 | 1.532 (7) |
C24—H24 | 0.9800 | C81—C83 | 1.540 (7) |
C25—H25A | 0.9600 | C81—H81A | 0.9800 |
C25—H25B | 0.9600 | C82—O82 | 1.225 (6) |
C25—H25C | 0.9600 | C82—N91 | 1.333 (7) |
C26—H26A | 0.9600 | C83—C84 | 1.520 (7) |
C26—H26B | 0.9600 | C83—H83A | 0.9700 |
C26—H26C | 0.9600 | C83—H83B | 0.9700 |
N31—C31 | 1.462 (5) | C84—C85' | 1.402 (12) |
N31—H31 | 0.8600 | C84—C86 | 1.456 (11) |
C31—C32 | 1.534 (5) | C84—C85 | 1.508 (9) |
C31—C33 | 1.529 (7) | C84—C86' | 1.642 (15) |
C31—H31A | 0.9800 | C84—H84 | 0.9800 |
C32—O32 | 1.237 (5) | C85—H85A | 0.9600 |
C32—N41 | 1.335 (6) | C85—H85B | 0.9600 |
C33—C34 | 1.536 (6) | C85—H85C | 0.9600 |
C33—H33A | 0.9700 | C86—H86A | 0.9600 |
C33—H33B | 0.9700 | C86—H86B | 0.9600 |
C34—C36 | 1.512 (9) | C86—H86C | 0.9600 |
C34—C35 | 1.515 (8) | C85'—H85D | 0.9600 |
C34—H34 | 0.9800 | C85'—H85E | 0.9600 |
C35—H35A | 0.9600 | C85'—H85F | 0.9600 |
C35—H35B | 0.9600 | C86'—H86D | 0.9600 |
C35—H35C | 0.9600 | C86'—H86E | 0.9600 |
C36—H36A | 0.9600 | C86'—H86F | 0.9600 |
C36—H36B | 0.9600 | N91—C91 | 1.463 (6) |
C36—H36C | 0.9600 | N91—H91 | 0.8600 |
N41—C41 | 1.460 (5) | C91—C92 | 1.526 (6) |
N41—H41 | 0.8600 | C91—C93 | 1.533 (7) |
C41—C42 | 1.528 (6) | C91—H91A | 0.9800 |
C41—C43 | 1.531 (6) | C92—O92 | 1.223 (6) |
C41—H41A | 0.9800 | C92—N101 | 1.344 (6) |
C42—O42 | 1.220 (6) | C93—C94 | 1.510 (7) |
C42—N51 | 1.346 (5) | C93—H93A | 0.9700 |
C43—C44 | 1.515 (6) | C93—H93B | 0.9700 |
C43—H43A | 0.9700 | C94—C95 | 1.406 (8) |
C43—H43B | 0.9700 | C94—C99 | 1.380 (8) |
C44—C45 | 1.384 (7) | C95—C96 | 1.394 (7) |
C44—C49 | 1.376 (7) | C95—H95 | 0.9300 |
C45—C46 | 1.391 (9) | C96—C97 | 1.365 (9) |
C45—H45 | 0.9300 | C96—H96 | 0.9300 |
C46—C47 | 1.368 (11) | C97—C98 | 1.376 (9) |
C46—H46 | 0.9300 | C97—H97 | 0.9300 |
C47—C48 | 1.356 (11) | C98—C99 | 1.397 (8) |
C47—H47 | 0.9300 | C98—H98 | 0.9300 |
C48—C49 | 1.392 (8) | C99—H99 | 0.9300 |
C48—H48 | 0.9300 | N101—C101 | 1.465 (5) |
C49—H49 | 0.9300 | N101—C105 | 1.474 (6) |
N51—C51 | 1.459 (6) | C101—C102 | 1.528 (5) |
N51—C55 | 1.476 (6) | C101—C103 | 1.533 (6) |
C51—C53 | 1.543 (7) | C101—H101 | 0.9800 |
C51—C52 | 1.544 (6) | C102—O102 | 1.235 (5) |
C51—H51 | 0.9800 | C103—C104 | 1.530 (7) |
C52—O52 | 1.237 (6) | C103—H10A | 0.9700 |
C52—N61 | 1.339 (6) | C103—H10B | 0.9700 |
C53—C54 | 1.521 (11) | C104—O104 | 1.419 (5) |
C53—H53A | 0.9700 | C104—C105 | 1.529 (6) |
C53—H53B | 0.9700 | C104—H104 | 0.9800 |
C54—O54 | 1.422 (6) | C105—H10C | 0.9700 |
C54—C55 | 1.534 (7) | C105—H10D | 0.9700 |
C54—H54A | 0.9800 | O104—H10E | 0.8200 |
C55—H55A | 0.9700 | O1M—C1M | 1.412 (8) |
C55—H55B | 0.9700 | O1M—H1M | 0.8200 |
O54—H54 | 0.8200 | C1M—H1M1 | 0.9600 |
N61—C61 | 1.460 (5) | C1M—H1M2 | 0.9600 |
N61—H61 | 0.8600 | C1M—H1M3 | 0.9600 |
C61—C62 | 1.536 (5) | O1W—H1W | 0.89 (2) |
C61—C63 | 1.533 (6) | O1W—H2W | 0.86 (3) |
C61—H61A | 0.9800 | O2M—C2M | 1.401 (11) |
C62—O62 | 1.229 (5) | O2M—H2MA | 0.87 (3) |
C62—N71 | 1.342 (5) | C2M—H2M1 | 0.9600 |
C63—C64 | 1.527 (6) | C2M—H2M2 | 0.9600 |
C63—C65 | 1.532 (6) | C2M—H2M3 | 0.9600 |
C102—N11—C11 | 123.9 (3) | C64—C63—H63 | 108.2 |
C102—N11—H11 | 118.1 | C65—C63—H63 | 108.2 |
C11—N11—H11 | 118.1 | C61—C63—H63 | 108.2 |
N11—C11—C12 | 107.4 (3) | C63—C64—H64A | 109.5 |
N11—C11—C13 | 110.5 (3) | C63—C64—H64B | 109.5 |
C12—C11—C13 | 110.7 (3) | H64A—C64—H64B | 109.5 |
N11—C11—H11A | 109.4 | C63—C64—H64C | 109.5 |
C12—C11—H11A | 109.4 | H64A—C64—H64C | 109.5 |
C13—C11—H11A | 109.4 | H64B—C64—H64C | 109.5 |
O12—C12—N21 | 124.2 (4) | C63—C65—H65A | 109.5 |
O12—C12—C11 | 120.0 (3) | C63—C65—H65B | 109.5 |
N21—C12—C11 | 115.7 (3) | H65A—C65—H65B | 109.5 |
C15—C13—C14 | 109.9 (4) | C63—C65—H65C | 109.5 |
C15—C13—C11 | 110.9 (4) | H65A—C65—H65C | 109.5 |
C14—C13—C11 | 111.2 (4) | H65B—C65—H65C | 109.5 |
C15—C13—H13 | 108.2 | C62—N71—C71 | 121.9 (3) |
C14—C13—H13 | 108.2 | C62—N71—H71 | 119.0 |
C11—C13—H13 | 108.2 | C71—N71—H71 | 119.0 |
C13—C14—H14A | 109.5 | N71—C71—C72 | 106.6 (3) |
C13—C14—H14B | 109.5 | N71—C71—C73 | 110.8 (3) |
H14A—C14—H14B | 109.5 | C72—C71—C73 | 110.6 (3) |
C13—C14—H14C | 109.5 | N71—C71—H71A | 109.6 |
H14A—C14—H14C | 109.5 | C72—C71—H71A | 109.6 |
H14B—C14—H14C | 109.5 | C73—C71—H71A | 109.6 |
C13—C15—H15A | 109.5 | O72—C72—N81 | 122.6 (4) |
C13—C15—H15B | 109.5 | O72—C72—C71 | 121.6 (4) |
H15A—C15—H15B | 109.5 | N81—C72—C71 | 115.7 (4) |
C13—C15—H15C | 109.5 | C71—C73—C74 | 114.7 (4) |
H15A—C15—H15C | 109.5 | C71—C73—H73A | 108.6 |
H15B—C15—H15C | 109.5 | C74—C73—H73A | 108.6 |
C12—N21—C21 | 123.0 (3) | C71—C73—H73B | 108.6 |
C12—N21—H21 | 118.5 | C74—C73—H73B | 108.6 |
C21—N21—H21 | 118.5 | H73A—C73—H73B | 107.6 |
N21—C21—C22 | 105.4 (3) | C76—C74—C73 | 110.5 (4) |
N21—C21—C23 | 108.9 (3) | C76—C74—C75 | 111.6 (4) |
C22—C21—C23 | 112.9 (3) | C73—C74—C75 | 112.3 (4) |
N21—C21—H21A | 109.8 | C76—C74—H74 | 107.4 |
C22—C21—H21A | 109.8 | C73—C74—H74 | 107.4 |
C23—C21—H21A | 109.8 | C75—C74—H74 | 107.4 |
O22—C22—N31 | 123.4 (4) | C74—C75—H75A | 109.5 |
O22—C22—C21 | 119.8 (4) | C74—C75—H75B | 109.5 |
N31—C22—C21 | 116.7 (3) | H75A—C75—H75B | 109.5 |
C24—C23—C21 | 117.2 (4) | C74—C75—H75C | 109.5 |
C24—C23—H23A | 108.0 | H75A—C75—H75C | 109.5 |
C21—C23—H23A | 108.0 | H75B—C75—H75C | 109.5 |
C24—C23—H23B | 108.0 | C74—C76—H76A | 109.5 |
C21—C23—H23B | 108.0 | C74—C76—H76B | 109.5 |
H23A—C23—H23B | 107.2 | H76A—C76—H76B | 109.5 |
C25—C24—C26 | 111.5 (5) | C74—C76—H76C | 109.5 |
C25—C24—C23 | 118.5 (5) | H76A—C76—H76C | 109.5 |
C26—C24—C23 | 108.4 (4) | H76B—C76—H76C | 109.5 |
C25—C24—H24 | 105.8 | C72—N81—C81 | 121.3 (4) |
C26—C24—H24 | 105.8 | C72—N81—H81 | 119.4 |
C23—C24—H24 | 105.8 | C81—N81—H81 | 119.4 |
C24—C25—H25A | 109.5 | N81—C81—C82 | 111.2 (4) |
C24—C25—H25B | 109.5 | N81—C81—C83 | 110.7 (4) |
H25A—C25—H25B | 109.5 | C82—C81—C83 | 109.2 (4) |
C24—C25—H25C | 109.5 | N81—C81—H81A | 108.6 |
H25A—C25—H25C | 109.5 | C82—C81—H81A | 108.6 |
H25B—C25—H25C | 109.5 | C83—C81—H81A | 108.6 |
C24—C26—H26A | 109.5 | O82—C82—N91 | 122.5 (5) |
C24—C26—H26B | 109.5 | O82—C82—C81 | 120.6 (5) |
H26A—C26—H26B | 109.5 | N91—C82—C81 | 116.9 (4) |
C24—C26—H26C | 109.5 | C81—C83—C84 | 114.8 (4) |
H26A—C26—H26C | 109.5 | C81—C83—H83A | 108.6 |
H26B—C26—H26C | 109.5 | C84—C83—H83A | 108.6 |
C22—N31—C31 | 121.9 (3) | C81—C83—H83B | 108.6 |
C22—N31—H31 | 119.1 | C84—C83—H83B | 108.6 |
C31—N31—H31 | 119.1 | H83A—C83—H83B | 107.5 |
N31—C31—C32 | 108.4 (3) | C86—C84—C85 | 114.9 (6) |
N31—C31—C33 | 111.1 (3) | C85'—C84—C83 | 118.7 (7) |
C32—C31—C33 | 109.1 (3) | C86—C84—C83 | 112.2 (6) |
N31—C31—H31A | 109.4 | C85—C84—C83 | 111.5 (5) |
C32—C31—H31A | 109.4 | C85'—C84—C86' | 105.8 (9) |
C33—C31—H31A | 109.4 | C83—C84—C86' | 102.4 (8) |
O32—C32—N41 | 122.0 (4) | C86—C84—H84 | 105.8 |
O32—C32—C31 | 120.6 (4) | C85—C84—H84 | 105.8 |
N41—C32—C31 | 117.4 (3) | C83—C84—H84 | 105.8 |
C34—C33—C31 | 114.9 (4) | C84—C85—H85A | 109.5 |
C34—C33—H33A | 108.5 | C84—C85—H85B | 109.5 |
C31—C33—H33A | 108.5 | H85A—C85—H85B | 109.5 |
C34—C33—H33B | 108.5 | C84—C85—H85C | 109.5 |
C31—C33—H33B | 108.5 | H85A—C85—H85C | 109.5 |
H33A—C33—H33B | 107.5 | H85B—C85—H85C | 109.5 |
C36—C34—C35 | 111.5 (5) | C84—C86—H86A | 109.5 |
C36—C34—C33 | 110.3 (5) | C84—C86—H86B | 109.5 |
C35—C34—C33 | 112.2 (4) | H86A—C86—H86B | 109.5 |
C36—C34—H34 | 107.5 | C84—C86—H86C | 109.5 |
C35—C34—H34 | 107.5 | H86A—C86—H86C | 109.5 |
C33—C34—H34 | 107.5 | H86B—C86—H86C | 109.5 |
C34—C35—H35A | 109.5 | C84—C85'—H85D | 109.5 |
C34—C35—H35B | 109.5 | C84—C85'—H85E | 109.5 |
H35A—C35—H35B | 109.5 | H85D—C85'—H85E | 109.5 |
C34—C35—H35C | 109.5 | C84—C85'—H85F | 109.5 |
H35A—C35—H35C | 109.5 | H85D—C85'—H85F | 109.5 |
H35B—C35—H35C | 109.5 | H85E—C85'—H85F | 109.5 |
C34—C36—H36A | 109.5 | C84—C86'—H86D | 109.5 |
C34—C36—H36B | 109.5 | C84—C86'—H86E | 109.5 |
H36A—C36—H36B | 109.5 | H86D—C86'—H86E | 109.5 |
C34—C36—H36C | 109.5 | C84—C86'—H86F | 109.5 |
H36A—C36—H36C | 109.5 | H86D—C86'—H86F | 109.5 |
H36B—C36—H36C | 109.5 | H86E—C86'—H86F | 109.5 |
C32—N41—C41 | 119.1 (3) | C82—N91—C91 | 121.3 (4) |
C32—N41—H41 | 120.5 | C82—N91—H91 | 119.3 |
C41—N41—H41 | 120.5 | C91—N91—H91 | 119.3 |
N41—C41—C42 | 109.8 (3) | N91—C91—C92 | 105.9 (3) |
N41—C41—C43 | 110.4 (3) | N91—C91—C93 | 112.5 (4) |
C42—C41—C43 | 109.0 (4) | C92—C91—C93 | 112.7 (4) |
N41—C41—H41A | 109.2 | N91—C91—H91A | 108.5 |
C42—C41—H41A | 109.2 | C92—C91—H91A | 108.5 |
C43—C41—H41A | 109.2 | C93—C91—H91A | 108.5 |
O42—C42—N51 | 122.2 (4) | O92—C92—N101 | 123.1 (4) |
O42—C42—C41 | 120.1 (4) | O92—C92—C91 | 120.7 (4) |
N51—C42—C41 | 117.7 (4) | N101—C92—C91 | 116.0 (4) |
C44—C43—C41 | 109.6 (4) | C94—C93—C91 | 110.7 (4) |
C44—C43—H43A | 109.7 | C94—C93—H93A | 109.5 |
C41—C43—H43A | 109.7 | C91—C93—H93A | 109.5 |
C44—C43—H43B | 109.7 | C94—C93—H93B | 109.5 |
C41—C43—H43B | 109.7 | C91—C93—H93B | 109.5 |
H43A—C43—H43B | 108.2 | H93A—C93—H93B | 108.1 |
C45—C44—C49 | 118.0 (5) | C95—C94—C99 | 118.7 (5) |
C45—C44—C43 | 121.6 (5) | C95—C94—C93 | 119.7 (5) |
C49—C44—C43 | 120.3 (4) | C99—C94—C93 | 121.7 (5) |
C44—C45—C46 | 120.5 (6) | C96—C95—C94 | 120.4 (5) |
C44—C45—H45 | 119.8 | C96—C95—H95 | 119.8 |
C46—C45—H45 | 119.8 | C94—C95—H95 | 119.8 |
C47—C46—C45 | 120.7 (6) | C95—C96—C97 | 119.7 (6) |
C47—C46—H46 | 119.7 | C95—C96—H96 | 120.1 |
C45—C46—H46 | 119.7 | C97—C96—H96 | 120.1 |
C46—C47—C48 | 119.1 (5) | C96—C97—C98 | 120.7 (5) |
C46—C47—H47 | 120.4 | C96—C97—H97 | 119.7 |
C48—C47—H47 | 120.4 | C98—C97—H97 | 119.7 |
C47—C48—C49 | 120.9 (6) | C99—C98—C97 | 120.1 (6) |
C47—C48—H48 | 119.6 | C99—C98—H98 | 119.9 |
C49—C48—H48 | 119.6 | C97—C98—H98 | 119.9 |
C44—C49—C48 | 120.7 (5) | C98—C99—C94 | 120.3 (5) |
C44—C49—H49 | 119.6 | C98—C99—H99 | 119.8 |
C48—C49—H49 | 119.6 | C94—C99—H99 | 119.8 |
C42—N51—C51 | 120.7 (4) | C92—N101—C101 | 119.7 (3) |
C42—N51—C55 | 126.5 (4) | C92—N101—C105 | 128.1 (4) |
C51—N51—C55 | 112.5 (4) | C101—N101—C105 | 112.2 (3) |
N51—C51—C53 | 101.6 (4) | N101—C101—C102 | 113.0 (3) |
N51—C51—C52 | 114.6 (4) | N101—C101—C103 | 103.4 (3) |
C53—C51—C52 | 111.8 (4) | C102—C101—C103 | 112.4 (3) |
N51—C51—H51 | 109.5 | N101—C101—H101 | 109.3 |
C53—C51—H51 | 109.5 | C102—C101—H101 | 109.3 |
C52—C51—H51 | 109.5 | C103—C101—H101 | 109.3 |
O52—C52—N61 | 124.4 (4) | O102—C102—N11 | 123.9 (4) |
O52—C52—C51 | 118.6 (4) | O102—C102—C101 | 119.1 (3) |
N61—C52—C51 | 116.9 (4) | N11—C102—C101 | 117.0 (3) |
C51—C53—C54 | 103.4 (4) | C104—C103—C101 | 104.2 (3) |
C51—C53—H53A | 111.1 | C104—C103—H10A | 110.9 |
C54—C53—H53A | 111.1 | C101—C103—H10A | 110.9 |
C51—C53—H53B | 111.1 | C104—C103—H10B | 110.9 |
C54—C53—H53B | 111.1 | C101—C103—H10B | 110.9 |
H53A—C53—H53B | 109.0 | H10A—C103—H10B | 108.9 |
O54—C54—C55 | 113.6 (5) | O104—C104—C103 | 109.8 (4) |
O54—C54—C53 | 110.8 (6) | O104—C104—C105 | 112.1 (4) |
C55—C54—C53 | 102.5 (5) | C103—C104—C105 | 104.1 (4) |
O54—C54—H54A | 109.9 | O104—C104—H104 | 110.2 |
C55—C54—H54A | 109.9 | C103—C104—H104 | 110.2 |
C53—C54—H54A | 109.9 | C105—C104—H104 | 110.2 |
N51—C55—C54 | 103.6 (5) | N101—C105—C104 | 104.6 (3) |
N51—C55—H55A | 111.0 | N101—C105—H10C | 110.8 |
C54—C55—H55A | 111.0 | C104—C105—H10C | 110.8 |
N51—C55—H55B | 111.0 | N101—C105—H10D | 110.8 |
C54—C55—H55B | 111.0 | C104—C105—H10D | 110.8 |
H55A—C55—H55B | 109.0 | H10C—C105—H10D | 108.9 |
C54—O54—H54 | 109.5 | C104—O104—H10E | 109.5 |
C52—N61—C61 | 122.4 (3) | C1M—O1M—H1M | 109.5 |
C52—N61—H61 | 118.8 | O1M—C1M—H1M1 | 109.5 |
C61—N61—H61 | 118.8 | O1M—C1M—H1M2 | 109.5 |
N61—C61—C62 | 109.7 (3) | H1M1—C1M—H1M2 | 109.5 |
N61—C61—C63 | 111.0 (3) | O1M—C1M—H1M3 | 109.5 |
C62—C61—C63 | 109.1 (3) | H1M1—C1M—H1M3 | 109.5 |
N61—C61—H61A | 109.0 | H1M2—C1M—H1M3 | 109.5 |
C62—C61—H61A | 109.0 | H1W—O1W—H2W | 103 (5) |
C63—C61—H61A | 109.0 | C2M—O2M—H2MA | 132 (7) |
O62—C62—N71 | 123.2 (4) | O2M—C2M—H2M1 | 109.5 |
O62—C62—C61 | 121.8 (4) | O2M—C2M—H2M2 | 109.5 |
N71—C62—C61 | 114.9 (3) | H2M1—C2M—H2M2 | 109.5 |
C64—C63—C65 | 111.2 (4) | O2M—C2M—H2M3 | 109.5 |
C64—C63—C61 | 110.1 (4) | H2M1—C2M—H2M3 | 109.5 |
C65—C63—C61 | 110.8 (4) | H2M2—C2M—H2M3 | 109.5 |
C102—N11—C11—C12 | −120.8 (4) | C52—N61—C61—C63 | 119.9 (4) |
C102—N11—C11—C13 | 118.3 (4) | N61—C61—C62—O62 | −62.7 (5) |
N11—C11—C12—O12 | −41.0 (5) | C63—C61—C62—O62 | 59.1 (5) |
C13—C11—C12—O12 | 79.7 (4) | N61—C61—C62—N71 | 120.1 (4) |
N11—C11—C12—N21 | 142.0 (3) | C63—C61—C62—N71 | −118.1 (4) |
C13—C11—C12—N21 | −97.2 (4) | N61—C61—C63—C64 | −59.8 (4) |
N11—C11—C13—C15 | −175.6 (4) | C62—C61—C63—C64 | 179.2 (3) |
C12—C11—C13—C15 | 65.5 (5) | N61—C61—C63—C65 | 176.7 (3) |
N11—C11—C13—C14 | −53.0 (5) | C62—C61—C63—C65 | 55.7 (4) |
C12—C11—C13—C14 | −171.9 (4) | O62—C62—N71—C71 | −6.6 (7) |
O12—C12—N21—C21 | 1.4 (6) | C61—C62—N71—C71 | 170.6 (4) |
C11—C12—N21—C21 | 178.2 (3) | C62—N71—C71—C72 | −98.0 (4) |
C12—N21—C21—C22 | −129.5 (4) | C62—N71—C71—C73 | 141.6 (4) |
C12—N21—C21—C23 | 109.0 (4) | N71—C71—C72—O72 | −72.7 (5) |
N21—C21—C22—O22 | −61.4 (5) | C73—C71—C72—O72 | 47.7 (5) |
C23—C21—C22—O22 | 57.4 (5) | N71—C71—C72—N81 | 107.2 (4) |
N21—C21—C22—N31 | 115.4 (4) | C73—C71—C72—N81 | −132.4 (4) |
C23—C21—C22—N31 | −125.8 (4) | N71—C71—C73—C74 | 174.7 (3) |
N21—C21—C23—C24 | −174.0 (4) | C72—C71—C73—C74 | 56.8 (5) |
C22—C21—C23—C24 | 69.2 (5) | C71—C73—C74—C76 | −171.1 (4) |
C21—C23—C24—C25 | −57.2 (7) | C71—C73—C74—C75 | 63.5 (6) |
C21—C23—C24—C26 | 174.5 (4) | O72—C72—N81—C81 | −2.5 (6) |
O22—C22—N31—C31 | −0.1 (6) | C71—C72—N81—C81 | 177.6 (4) |
C21—C22—N31—C31 | −176.7 (3) | C72—N81—C81—C82 | −80.4 (5) |
C22—N31—C31—C32 | −120.3 (4) | C72—N81—C81—C83 | 158.1 (4) |
C22—N31—C31—C33 | 119.8 (4) | N81—C81—C82—O82 | 150.9 (5) |
N31—C31—C32—O32 | −82.4 (5) | C83—C81—C82—O82 | −86.7 (6) |
C33—C31—C32—O32 | 38.7 (5) | N81—C81—C82—N91 | −32.5 (5) |
N31—C31—C32—N41 | 97.3 (4) | C83—C81—C82—N91 | 89.9 (5) |
C33—C31—C32—N41 | −141.5 (4) | N81—C81—C83—C84 | −63.2 (5) |
N31—C31—C33—C34 | −59.7 (5) | C82—C81—C83—C84 | 174.1 (4) |
C32—C31—C33—C34 | −179.2 (4) | C81—C83—C84—C85' | 91.4 (9) |
C31—C33—C34—C36 | −179.6 (5) | C81—C83—C84—C86 | 168.9 (7) |
C31—C33—C34—C35 | −54.6 (6) | C81—C83—C84—C85 | −60.5 (7) |
O32—C32—N41—C41 | −1.1 (6) | C81—C83—C84—C86' | −152.6 (9) |
C31—C32—N41—C41 | 179.2 (4) | O82—C82—N91—C91 | −3.0 (8) |
C32—N41—C41—C42 | 56.3 (5) | C81—C82—N91—C91 | −179.5 (4) |
C32—N41—C41—C43 | 176.5 (4) | C82—N91—C91—C92 | 146.8 (4) |
N41—C41—C42—O42 | 57.0 (5) | C82—N91—C91—C93 | −89.7 (6) |
C43—C41—C42—O42 | −64.0 (5) | N91—C91—C92—O92 | 82.8 (5) |
N41—C41—C42—N51 | −124.7 (4) | C93—C91—C92—O92 | −40.6 (5) |
C43—C41—C42—N51 | 114.3 (4) | N91—C91—C92—N101 | −92.4 (4) |
N41—C41—C43—C44 | 175.5 (4) | C93—C91—C92—N101 | 144.2 (4) |
C42—C41—C43—C44 | −63.8 (5) | N91—C91—C93—C94 | 160.7 (4) |
C41—C43—C44—C45 | 91.0 (6) | C92—C91—C93—C94 | −79.6 (5) |
C41—C43—C44—C49 | −85.5 (6) | C91—C93—C94—C95 | −68.2 (6) |
C49—C44—C45—C46 | 1.1 (8) | C91—C93—C94—C99 | 113.0 (5) |
C43—C44—C45—C46 | −175.5 (5) | C99—C94—C95—C96 | 2.0 (7) |
C44—C45—C46—C47 | −1.2 (10) | C93—C94—C95—C96 | −176.9 (5) |
C45—C46—C47—C48 | 0.2 (10) | C94—C95—C96—C97 | −0.6 (8) |
C46—C47—C48—C49 | 1.0 (10) | C95—C96—C97—C98 | −1.4 (8) |
C45—C44—C49—C48 | 0.0 (8) | C96—C97—C98—C99 | 2.0 (8) |
C43—C44—C49—C48 | 176.6 (5) | C97—C98—C99—C94 | −0.6 (8) |
C47—C48—C49—C44 | −1.1 (10) | C95—C94—C99—C98 | −1.4 (7) |
O42—C42—N51—C51 | 5.0 (6) | C93—C94—C99—C98 | 177.5 (5) |
C41—C42—N51—C51 | −173.3 (4) | O92—C92—N101—C101 | 0.1 (6) |
O42—C42—N51—C55 | 178.7 (4) | C91—C92—N101—C101 | 175.1 (3) |
C41—C42—N51—C55 | 0.5 (6) | O92—C92—N101—C105 | 176.5 (4) |
C42—N51—C51—C53 | 156.4 (4) | C91—C92—N101—C105 | −8.5 (6) |
C55—N51—C51—C53 | −18.2 (5) | C92—N101—C101—C102 | −77.2 (5) |
C42—N51—C51—C52 | −82.9 (5) | C105—N101—C101—C102 | 105.9 (4) |
C55—N51—C51—C52 | 102.6 (5) | C92—N101—C101—C103 | 161.0 (3) |
N51—C51—C52—O52 | −172.5 (4) | C105—N101—C101—C103 | −16.0 (4) |
C53—C51—C52—O52 | −57.6 (7) | C11—N11—C102—O102 | −2.5 (7) |
N51—C51—C52—N61 | 9.2 (6) | C11—N11—C102—C101 | 178.4 (3) |
C53—C51—C52—N61 | 124.2 (5) | N101—C101—C102—O102 | 168.4 (4) |
N51—C51—C53—C54 | 35.8 (5) | C103—C101—C102—O102 | −75.0 (5) |
C52—C51—C53—C54 | −86.8 (5) | N101—C101—C102—N11 | −12.4 (5) |
C51—C53—C54—O54 | −161.8 (4) | C103—C101—C102—N11 | 104.2 (4) |
C51—C53—C54—C55 | −40.3 (5) | N101—C101—C103—C104 | 30.5 (4) |
C42—N51—C55—C54 | 179.3 (4) | C102—C101—C103—C104 | −91.7 (4) |
C51—N51—C55—C54 | −6.4 (5) | C101—C103—C104—O104 | −154.1 (3) |
O54—C54—C55—N51 | 148.4 (6) | C101—C103—C104—C105 | −34.0 (4) |
C53—C54—C55—N51 | 28.8 (5) | C92—N101—C105—C104 | 178.3 (4) |
O52—C52—N61—C61 | 3.1 (7) | C101—N101—C105—C104 | −5.1 (4) |
C51—C52—N61—C61 | −178.8 (4) | O104—C104—C105—N101 | 142.7 (4) |
C52—N61—C61—C62 | −119.4 (4) | C103—C104—C105—N101 | 24.1 (4) |
D—H···A | H···A | D···A | D—H···A |
N31—H31···O62 | 2.01 | 2.838 (5) | 162 |
N61—H61···O32 | 2.22 | 3.048 (5) | 160 |
N81—H81···O12 | 2.19 | 2.905 (4) | 140 |
N21—H21···O52i | 2.25 | 3.090 (4) | 165 |
N41—H41···O72i | 2.13 | 2.966 (5) | 165 |
N71—H71···O22ii | 1.97 | 2.818 (4) | 168 |
O104—H10E···O102iii | 2.06 | 2.869 (5) | 168 |
O54—H54···O2M | 1.99 | 2.725 (9) | 149 |
O1W—H2W···O54 | 2.01 | 2.847 (7) | 163 |
O1W—H1W···O102ii | 2.03 | 2.927 (6) | 178 |
O1M—H1M···O42 | 2.03 | 2.831 (5) | 166 |
O2M—H2MA···O82iv | 1.99 | 2.727 (8) | 144 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x+1/2, −y+3/2, −z+1; (iv) −x+3/2, −y+1, z−1/2. |
C62H94N10O12·H2O | Dx = 1.190 Mg m−3 |
Mr = 1189.48 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 24836 reflections |
a = 12.0818 (1) Å | θ = 4.3–60.5° |
b = 19.0030 (2) Å | µ = 0.68 mm−1 |
c = 28.9218 (2) Å | T = 100 K |
V = 6640.17 (10) Å3 | Needle, colourless |
Z = 4 | 0.40 × 0.10 × 0.05 mm |
F(000) = 2568 |
RIGAKU Xtalab P200K diffractometer | 9942 independent reflections |
Radiation source: Rotating-anode | 9728 reflections with I > 2σ(I) |
Detector resolution: 5.8140 pixels mm-1 | Rint = 0.023 |
ω–scan | θmax = 60.7°, θmin = 2.8° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015) | h = −13→13 |
Tmin = 0.830, Tmax = 1.000 | k = −21→15 |
31704 measured reflections | l = −30→32 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.030 | w = 1/[σ2(Fo2) + (0.0557P)2 + 1.1936P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.082 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.84 e Å−3 |
9942 reflections | Δρmin = −0.21 e Å−3 |
768 parameters | Absolute structure: Flack x determined using 4245 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
3 restraints | Absolute structure parameter: 0.00 (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 | ||
O1W | 1.11656 (19) | 0.39526 (14) | 0.56999 (8) | 0.0637 (7) | |
H1 | 1.065590 | 0.371799 | 0.556029 | 0.095* | |
H2 | 1.163177 | 0.399193 | 0.544564 | 0.095* | |
N11 | 0.49693 (15) | 0.46552 (9) | 0.84981 (6) | 0.0172 (4) | |
H11 | 0.500365 | 0.420578 | 0.852989 | 0.021* | |
C11 | 0.56657 (18) | 0.49995 (11) | 0.81524 (7) | 0.0168 (4) | |
H11A | 0.542514 | 0.548992 | 0.812259 | 0.020* | |
C12 | 0.55215 (17) | 0.46381 (11) | 0.76838 (7) | 0.0161 (4) | |
O12 | 0.57959 (13) | 0.40185 (8) | 0.76198 (5) | 0.0213 (3) | |
C13 | 0.68963 (19) | 0.49944 (12) | 0.82868 (7) | 0.0214 (5) | |
H13 | 0.712888 | 0.450504 | 0.833162 | 0.026* | |
C14 | 0.7063 (2) | 0.53910 (13) | 0.87403 (8) | 0.0262 (5) | |
H14A | 0.661653 | 0.518032 | 0.897732 | 0.039* | |
H14B | 0.782870 | 0.536817 | 0.882846 | 0.039* | |
H14C | 0.685030 | 0.587383 | 0.870050 | 0.039* | |
C15 | 0.7594 (2) | 0.53143 (14) | 0.79019 (8) | 0.0297 (6) | |
H15A | 0.747532 | 0.505670 | 0.762063 | 0.045* | |
H15B | 0.738374 | 0.579668 | 0.785716 | 0.045* | |
H15C | 0.836214 | 0.529103 | 0.798513 | 0.045* | |
N21 | 0.51141 (15) | 0.50507 (9) | 0.73457 (6) | 0.0169 (4) | |
H21 | 0.486367 | 0.545979 | 0.741801 | 0.020* | |
C21 | 0.50792 (18) | 0.48343 (11) | 0.68628 (7) | 0.0162 (4) | |
H21A | 0.513364 | 0.432077 | 0.684214 | 0.019* | |
C22 | 0.60621 (18) | 0.51718 (11) | 0.66167 (7) | 0.0159 (4) | |
O22 | 0.61337 (13) | 0.58172 (8) | 0.65797 (6) | 0.0235 (3) | |
C23 | 0.40097 (18) | 0.50821 (11) | 0.66347 (7) | 0.0183 (5) | |
H23A | 0.392852 | 0.558294 | 0.668978 | 0.022* | |
H23B | 0.339232 | 0.484715 | 0.678350 | 0.022* | |
C24 | 0.39375 (19) | 0.49492 (12) | 0.61123 (7) | 0.0211 (5) | |
H24 | 0.459697 | 0.515415 | 0.596804 | 0.025* | |
C25 | 0.3918 (2) | 0.41647 (13) | 0.59970 (8) | 0.0260 (5) | |
H25A | 0.455957 | 0.394149 | 0.612664 | 0.039* | |
H25B | 0.326221 | 0.395539 | 0.612442 | 0.039* | |
H25C | 0.391952 | 0.410429 | 0.566743 | 0.039* | |
C26 | 0.2926 (2) | 0.53148 (13) | 0.59097 (9) | 0.0304 (6) | |
H26A | 0.294915 | 0.580667 | 0.598479 | 0.046* | |
H26B | 0.292371 | 0.525852 | 0.557984 | 0.046* | |
H26C | 0.226641 | 0.510962 | 0.603683 | 0.046* | |
N31 | 0.68209 (15) | 0.47322 (9) | 0.64386 (6) | 0.0188 (4) | |
H31 | 0.675201 | 0.428636 | 0.648097 | 0.023* | |
C31 | 0.77551 (18) | 0.49975 (12) | 0.61758 (8) | 0.0209 (5) | |
H31A | 0.786616 | 0.548872 | 0.626786 | 0.025* | |
C32 | 0.75633 (19) | 0.49926 (11) | 0.56563 (8) | 0.0211 (5) | |
O32 | 0.80457 (15) | 0.54166 (9) | 0.54075 (6) | 0.0320 (4) | |
C33 | 0.8826 (2) | 0.45997 (13) | 0.62899 (9) | 0.0276 (5) | |
H33A | 0.872183 | 0.410497 | 0.621980 | 0.033* | |
H33B | 0.941432 | 0.477426 | 0.609240 | 0.033* | |
C34 | 0.9188 (2) | 0.46708 (14) | 0.67944 (9) | 0.0313 (6) | |
H34 | 0.861431 | 0.445911 | 0.698934 | 0.038* | |
C35 | 1.0262 (2) | 0.42664 (19) | 0.68717 (11) | 0.0488 (8) | |
H35A | 1.016180 | 0.378471 | 0.678073 | 0.073* | |
H35B | 1.084135 | 0.447380 | 0.669002 | 0.073* | |
H35C | 1.045871 | 0.428589 | 0.719302 | 0.073* | |
C36 | 0.9314 (2) | 0.54399 (16) | 0.69351 (10) | 0.0416 (7) | |
H36A | 0.862870 | 0.568296 | 0.688334 | 0.062* | |
H36B | 0.950523 | 0.546653 | 0.725685 | 0.062* | |
H36C | 0.988787 | 0.565443 | 0.675385 | 0.062* | |
N41 | 0.68870 (16) | 0.44902 (10) | 0.54849 (6) | 0.0220 (4) | |
H41 | 0.662016 | 0.417547 | 0.566717 | 0.026* | |
C41 | 0.66014 (19) | 0.44741 (12) | 0.49921 (8) | 0.0210 (5) | |
H41A | 0.718002 | 0.472428 | 0.482072 | 0.025* | |
C42 | 0.66122 (18) | 0.37014 (12) | 0.48399 (7) | 0.0191 (5) | |
O42 | 0.57421 (13) | 0.33785 (8) | 0.47746 (6) | 0.0257 (4) | |
C43 | 0.5491 (2) | 0.48405 (13) | 0.48979 (8) | 0.0258 (5) | |
H43A | 0.489907 | 0.450059 | 0.493519 | 0.031* | |
H43B | 0.538336 | 0.520757 | 0.512653 | 0.031* | |
C44 | 0.54101 (19) | 0.51617 (12) | 0.44214 (8) | 0.0223 (5) | |
C45 | 0.6101 (2) | 0.57210 (12) | 0.42997 (8) | 0.0255 (5) | |
H45 | 0.662560 | 0.588141 | 0.450992 | 0.031* | |
C46 | 0.6016 (2) | 0.60394 (13) | 0.38725 (9) | 0.0300 (6) | |
H46 | 0.647813 | 0.641399 | 0.379782 | 0.036* | |
C47 | 0.5248 (2) | 0.58031 (14) | 0.35561 (9) | 0.0338 (6) | |
H47 | 0.519164 | 0.601836 | 0.326822 | 0.041* | |
C48 | 0.4562 (2) | 0.52472 (15) | 0.36664 (9) | 0.0343 (6) | |
H48 | 0.404521 | 0.508567 | 0.345281 | 0.041* | |
C49 | 0.4645 (2) | 0.49285 (13) | 0.40994 (9) | 0.0290 (5) | |
H49 | 0.418128 | 0.455431 | 0.417288 | 0.035* | |
N51 | 0.76144 (15) | 0.33929 (9) | 0.48141 (6) | 0.0169 (4) | |
C51 | 0.77331 (19) | 0.26394 (11) | 0.47106 (7) | 0.0189 (5) | |
H51 | 0.722867 | 0.250970 | 0.445933 | 0.023* | |
C52 | 0.75260 (17) | 0.21626 (11) | 0.51290 (7) | 0.0165 (5) | |
O52 | 0.75486 (13) | 0.15226 (8) | 0.50807 (5) | 0.0225 (3) | |
C53 | 0.89348 (19) | 0.25888 (12) | 0.45410 (7) | 0.0217 (5) | |
H53A | 0.924203 | 0.212690 | 0.460343 | 0.026* | |
H53B | 0.898342 | 0.268284 | 0.421202 | 0.026* | |
C54 | 0.95295 (18) | 0.31523 (12) | 0.48180 (7) | 0.0199 (5) | |
H54 | 1.021136 | 0.330168 | 0.466289 | 0.024* | |
O54 | 0.97469 (13) | 0.29255 (8) | 0.52782 (5) | 0.0224 (3) | |
H54A | 1.005417 | 0.254084 | 0.527207 | 0.034* | |
C55 | 0.86995 (18) | 0.37504 (12) | 0.48432 (8) | 0.0201 (5) | |
H55A | 0.877089 | 0.400638 | 0.513182 | 0.024* | |
H55B | 0.879863 | 0.407506 | 0.458775 | 0.024* | |
N61 | 0.73065 (15) | 0.24835 (9) | 0.55318 (6) | 0.0170 (4) | |
H61 | 0.726006 | 0.293502 | 0.553610 | 0.020* | |
C61 | 0.71437 (18) | 0.21002 (11) | 0.59613 (7) | 0.0164 (4) | |
H61A | 0.676135 | 0.165747 | 0.589279 | 0.020* | |
C62 | 0.64029 (17) | 0.25485 (11) | 0.62684 (7) | 0.0160 (4) | |
O62 | 0.64590 (12) | 0.32020 (8) | 0.62613 (5) | 0.0206 (3) | |
C63 | 0.82721 (19) | 0.19290 (12) | 0.61947 (8) | 0.0218 (5) | |
H63 | 0.873429 | 0.170281 | 0.595917 | 0.026* | |
C64 | 0.8141 (2) | 0.14023 (14) | 0.65875 (8) | 0.0300 (6) | |
H64A | 0.774565 | 0.099692 | 0.647811 | 0.045* | |
H64B | 0.885854 | 0.126138 | 0.669601 | 0.045* | |
H64C | 0.773627 | 0.161631 | 0.683611 | 0.045* | |
C65 | 0.8898 (2) | 0.25790 (14) | 0.63592 (8) | 0.0293 (5) | |
H65A | 0.897357 | 0.290512 | 0.610760 | 0.044* | |
H65B | 0.849687 | 0.279811 | 0.660681 | 0.044* | |
H65C | 0.961914 | 0.244318 | 0.646670 | 0.044* | |
N71 | 0.57177 (15) | 0.21863 (9) | 0.65399 (6) | 0.0163 (4) | |
H71 | 0.566887 | 0.173950 | 0.649749 | 0.020* | |
C71 | 0.50404 (18) | 0.25023 (11) | 0.69074 (7) | 0.0165 (4) | |
H71A | 0.520956 | 0.300501 | 0.693403 | 0.020* | |
C72 | 0.53582 (17) | 0.21271 (11) | 0.73508 (7) | 0.0155 (4) | |
O72 | 0.52627 (13) | 0.14809 (8) | 0.73774 (5) | 0.0216 (3) | |
C73 | 0.38058 (19) | 0.24023 (12) | 0.68044 (8) | 0.0215 (5) | |
H73A | 0.362406 | 0.267173 | 0.652984 | 0.026* | |
H73B | 0.367945 | 0.191009 | 0.673304 | 0.026* | |
C74 | 0.3007 (2) | 0.26180 (14) | 0.71914 (8) | 0.0285 (5) | |
H74 | 0.318378 | 0.234341 | 0.746859 | 0.034* | |
C75 | 0.1829 (2) | 0.24395 (16) | 0.70409 (13) | 0.0475 (8) | |
H75A | 0.178364 | 0.194813 | 0.696622 | 0.071* | |
H75B | 0.132461 | 0.254447 | 0.728794 | 0.071* | |
H75C | 0.163759 | 0.271375 | 0.677380 | 0.071* | |
C76 | 0.3089 (2) | 0.33960 (13) | 0.73107 (9) | 0.0292 (5) | |
H76A | 0.383192 | 0.350419 | 0.740498 | 0.044* | |
H76B | 0.290034 | 0.367204 | 0.704415 | 0.044* | |
H76C | 0.258736 | 0.350276 | 0.755829 | 0.044* | |
N81 | 0.57450 (15) | 0.25333 (9) | 0.76917 (6) | 0.0173 (4) | |
H81 | 0.578985 | 0.297996 | 0.764751 | 0.021* | |
C81 | 0.60941 (19) | 0.22454 (12) | 0.81365 (7) | 0.0185 (5) | |
H81A | 0.594862 | 0.173811 | 0.814238 | 0.022* | |
C82 | 0.53993 (18) | 0.26082 (11) | 0.85108 (7) | 0.0165 (4) | |
O82 | 0.57012 (13) | 0.31670 (8) | 0.86852 (5) | 0.0197 (3) | |
C83 | 0.7324 (2) | 0.23763 (13) | 0.82220 (8) | 0.0261 (5) | |
H83A | 0.744789 | 0.288035 | 0.823312 | 0.031* | |
H83B | 0.751505 | 0.218678 | 0.852304 | 0.031* | |
C84 | 0.8107 (2) | 0.20600 (13) | 0.78637 (9) | 0.0280 (5) | |
H84 | 0.792749 | 0.226641 | 0.756232 | 0.034* | |
C85 | 0.7986 (2) | 0.12670 (13) | 0.78243 (8) | 0.0265 (5) | |
H85A | 0.723296 | 0.115225 | 0.774981 | 0.040* | |
H85B | 0.846581 | 0.109536 | 0.758498 | 0.040* | |
H85C | 0.818275 | 0.105202 | 0.811320 | 0.040* | |
C86 | 0.9297 (2) | 0.22571 (17) | 0.79820 (13) | 0.0511 (8) | |
H86A | 0.935830 | 0.275951 | 0.800550 | 0.077* | |
H86B | 0.949910 | 0.204633 | 0.827152 | 0.077* | |
H86C | 0.978217 | 0.208967 | 0.774330 | 0.077* | |
N91 | 0.44509 (16) | 0.22898 (9) | 0.86294 (6) | 0.0203 (4) | |
H91 | 0.425515 | 0.190375 | 0.849749 | 0.024* | |
C91 | 0.37527 (18) | 0.26076 (11) | 0.89865 (7) | 0.0198 (5) | |
H91A | 0.415204 | 0.260104 | 0.928140 | 0.024* | |
C92 | 0.35026 (18) | 0.33736 (11) | 0.88548 (7) | 0.0184 (5) | |
O92 | 0.30707 (14) | 0.35086 (8) | 0.84808 (5) | 0.0251 (4) | |
C93 | 0.2664 (2) | 0.22003 (12) | 0.90416 (8) | 0.0248 (5) | |
H93A | 0.218694 | 0.229021 | 0.877849 | 0.030* | |
H93B | 0.281414 | 0.169916 | 0.905414 | 0.030* | |
C94 | 0.20953 (18) | 0.24314 (12) | 0.94815 (8) | 0.0216 (5) | |
C95 | 0.2366 (2) | 0.21121 (13) | 0.98984 (9) | 0.0299 (6) | |
H95 | 0.284873 | 0.173110 | 0.989887 | 0.036* | |
C96 | 0.1934 (2) | 0.23478 (14) | 1.03120 (8) | 0.0313 (6) | |
H96 | 0.211903 | 0.212280 | 1.058685 | 0.038* | |
C97 | 0.1226 (2) | 0.29173 (13) | 1.03172 (9) | 0.0284 (5) | |
H97 | 0.094492 | 0.308560 | 1.059535 | 0.034* | |
C98 | 0.0941 (2) | 0.32349 (14) | 0.99045 (9) | 0.0335 (6) | |
H98 | 0.045609 | 0.361525 | 0.990541 | 0.040* | |
C99 | 0.1368 (2) | 0.29931 (14) | 0.94891 (9) | 0.0297 (6) | |
H99 | 0.116401 | 0.321003 | 0.921376 | 0.036* | |
N101 | 0.37693 (15) | 0.38768 (9) | 0.91646 (6) | 0.0175 (4) | |
C101 | 0.34819 (19) | 0.46171 (11) | 0.90807 (8) | 0.0203 (5) | |
H101 | 0.273900 | 0.463679 | 0.894531 | 0.024* | |
C102 | 0.42811 (18) | 0.50244 (11) | 0.87656 (7) | 0.0185 (5) | |
O102 | 0.42011 (14) | 0.56717 (8) | 0.87509 (5) | 0.0271 (4) | |
C103 | 0.3431 (2) | 0.49189 (13) | 0.95715 (8) | 0.0281 (5) | |
H10A | 0.360341 | 0.541741 | 0.957243 | 0.034* | |
H10B | 0.270457 | 0.484943 | 0.970693 | 0.034* | |
C104 | 0.4303 (2) | 0.45028 (12) | 0.98296 (8) | 0.0266 (5) | |
H104 | 0.418123 | 0.451855 | 1.016445 | 0.032* | |
O104 | 0.53551 (16) | 0.47815 (9) | 0.97080 (6) | 0.0344 (4) | |
H10C | 0.581010 | 0.467318 | 0.990591 | 0.052* | |
C105 | 0.4174 (2) | 0.37607 (12) | 0.96414 (7) | 0.0208 (5) | |
H10D | 0.487700 | 0.351379 | 0.964094 | 0.025* | |
H10E | 0.364330 | 0.349383 | 0.982175 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1W | 0.0419 (12) | 0.0856 (18) | 0.0635 (14) | −0.0218 (12) | 0.0141 (11) | −0.0452 (13) |
N11 | 0.0227 (9) | 0.0110 (8) | 0.0179 (9) | 0.0013 (7) | 0.0039 (7) | 0.0019 (7) |
C11 | 0.0218 (11) | 0.0122 (10) | 0.0164 (10) | 0.0010 (9) | 0.0011 (9) | 0.0021 (8) |
C12 | 0.0150 (10) | 0.0137 (11) | 0.0196 (11) | −0.0013 (9) | 0.0018 (8) | 0.0012 (8) |
O12 | 0.0302 (9) | 0.0124 (8) | 0.0212 (8) | 0.0028 (7) | −0.0015 (7) | −0.0002 (6) |
C13 | 0.0218 (12) | 0.0214 (11) | 0.0210 (11) | 0.0011 (9) | −0.0005 (9) | −0.0011 (9) |
C14 | 0.0276 (12) | 0.0269 (13) | 0.0240 (12) | 0.0016 (10) | −0.0052 (10) | −0.0021 (10) |
C15 | 0.0237 (12) | 0.0367 (14) | 0.0288 (13) | −0.0072 (11) | 0.0023 (10) | −0.0034 (11) |
N21 | 0.0221 (10) | 0.0120 (9) | 0.0165 (9) | 0.0030 (7) | 0.0017 (7) | −0.0019 (7) |
C21 | 0.0218 (11) | 0.0119 (10) | 0.0150 (10) | 0.0001 (9) | 0.0015 (9) | −0.0005 (8) |
C22 | 0.0201 (11) | 0.0134 (11) | 0.0143 (10) | 0.0007 (9) | −0.0028 (9) | −0.0018 (8) |
O22 | 0.0260 (8) | 0.0136 (8) | 0.0309 (9) | 0.0006 (7) | 0.0049 (7) | 0.0018 (6) |
C23 | 0.0205 (11) | 0.0159 (11) | 0.0186 (11) | 0.0006 (9) | 0.0022 (9) | −0.0010 (9) |
C24 | 0.0234 (12) | 0.0218 (12) | 0.0182 (11) | −0.0015 (9) | −0.0013 (9) | 0.0011 (9) |
C25 | 0.0322 (13) | 0.0260 (13) | 0.0198 (12) | 0.0027 (10) | −0.0041 (10) | −0.0041 (9) |
C26 | 0.0378 (14) | 0.0267 (13) | 0.0267 (13) | 0.0023 (11) | −0.0083 (11) | 0.0030 (10) |
N31 | 0.0208 (9) | 0.0126 (9) | 0.0231 (9) | 0.0008 (8) | 0.0025 (8) | −0.0006 (7) |
C31 | 0.0200 (11) | 0.0160 (11) | 0.0267 (12) | −0.0014 (9) | 0.0054 (9) | −0.0029 (9) |
C32 | 0.0188 (11) | 0.0161 (11) | 0.0284 (12) | 0.0019 (9) | 0.0068 (9) | −0.0008 (10) |
O32 | 0.0390 (10) | 0.0260 (9) | 0.0309 (9) | −0.0088 (8) | 0.0072 (8) | 0.0024 (7) |
C33 | 0.0209 (11) | 0.0290 (13) | 0.0330 (13) | 0.0010 (10) | 0.0026 (10) | −0.0037 (10) |
C34 | 0.0223 (12) | 0.0407 (15) | 0.0310 (13) | −0.0033 (11) | 0.0022 (10) | −0.0023 (11) |
C35 | 0.0313 (15) | 0.072 (2) | 0.0430 (17) | 0.0083 (15) | −0.0082 (13) | −0.0014 (15) |
C36 | 0.0399 (15) | 0.0505 (17) | 0.0344 (14) | −0.0174 (14) | −0.0004 (12) | −0.0072 (13) |
N41 | 0.0262 (10) | 0.0186 (9) | 0.0213 (10) | −0.0028 (8) | 0.0060 (8) | 0.0025 (7) |
C41 | 0.0243 (11) | 0.0197 (11) | 0.0191 (11) | 0.0020 (9) | 0.0050 (9) | 0.0021 (9) |
C42 | 0.0205 (12) | 0.0212 (11) | 0.0157 (10) | −0.0011 (10) | 0.0010 (9) | 0.0053 (9) |
O42 | 0.0203 (8) | 0.0251 (8) | 0.0316 (9) | −0.0022 (7) | −0.0004 (7) | 0.0038 (7) |
C43 | 0.0249 (12) | 0.0235 (12) | 0.0288 (13) | 0.0052 (10) | 0.0060 (10) | 0.0032 (10) |
C44 | 0.0221 (12) | 0.0187 (11) | 0.0262 (12) | 0.0064 (9) | 0.0064 (9) | 0.0009 (9) |
C45 | 0.0290 (12) | 0.0210 (12) | 0.0266 (12) | −0.0017 (10) | 0.0017 (10) | −0.0040 (10) |
C46 | 0.0356 (14) | 0.0241 (13) | 0.0304 (13) | −0.0028 (11) | 0.0067 (11) | 0.0035 (10) |
C47 | 0.0426 (15) | 0.0325 (14) | 0.0263 (13) | 0.0053 (12) | 0.0010 (11) | 0.0061 (11) |
C48 | 0.0306 (13) | 0.0394 (15) | 0.0329 (14) | 0.0001 (11) | −0.0047 (11) | −0.0003 (11) |
C49 | 0.0232 (12) | 0.0281 (13) | 0.0358 (13) | −0.0011 (10) | 0.0023 (11) | 0.0012 (10) |
N51 | 0.0194 (9) | 0.0131 (9) | 0.0182 (9) | −0.0016 (7) | 0.0008 (7) | 0.0008 (7) |
C51 | 0.0226 (11) | 0.0177 (11) | 0.0164 (10) | −0.0018 (9) | 0.0004 (9) | −0.0007 (9) |
C52 | 0.0128 (10) | 0.0189 (12) | 0.0177 (11) | −0.0029 (8) | −0.0006 (8) | −0.0002 (9) |
O52 | 0.0316 (9) | 0.0147 (8) | 0.0214 (8) | −0.0001 (6) | 0.0022 (7) | −0.0008 (6) |
C53 | 0.0266 (12) | 0.0216 (12) | 0.0169 (11) | −0.0003 (10) | 0.0056 (9) | −0.0015 (9) |
C54 | 0.0184 (11) | 0.0223 (12) | 0.0189 (11) | −0.0007 (9) | 0.0054 (9) | 0.0010 (9) |
O54 | 0.0212 (8) | 0.0214 (8) | 0.0245 (8) | 0.0022 (6) | −0.0002 (6) | 0.0025 (6) |
C55 | 0.0191 (11) | 0.0178 (11) | 0.0233 (11) | −0.0040 (9) | 0.0028 (9) | 0.0020 (9) |
N61 | 0.0211 (9) | 0.0129 (9) | 0.0169 (9) | −0.0013 (7) | 0.0021 (7) | 0.0018 (7) |
C61 | 0.0190 (10) | 0.0154 (10) | 0.0148 (10) | −0.0008 (9) | 0.0012 (9) | 0.0010 (8) |
C62 | 0.0166 (10) | 0.0175 (12) | 0.0141 (10) | 0.0002 (8) | −0.0029 (8) | 0.0009 (8) |
O62 | 0.0255 (8) | 0.0126 (8) | 0.0237 (8) | −0.0017 (6) | 0.0032 (6) | 0.0007 (6) |
C63 | 0.0202 (11) | 0.0249 (12) | 0.0202 (11) | 0.0036 (10) | 0.0006 (9) | 0.0003 (9) |
C64 | 0.0280 (13) | 0.0352 (14) | 0.0269 (12) | 0.0097 (11) | −0.0028 (11) | 0.0072 (11) |
C65 | 0.0240 (12) | 0.0366 (14) | 0.0272 (12) | −0.0012 (11) | −0.0067 (10) | −0.0032 (11) |
N71 | 0.0213 (9) | 0.0110 (8) | 0.0168 (8) | −0.0003 (7) | 0.0037 (7) | −0.0017 (7) |
C71 | 0.0189 (11) | 0.0142 (10) | 0.0165 (10) | −0.0002 (9) | 0.0025 (8) | −0.0017 (8) |
C72 | 0.0160 (10) | 0.0138 (11) | 0.0167 (10) | 0.0004 (8) | 0.0050 (8) | −0.0012 (8) |
O72 | 0.0310 (9) | 0.0130 (8) | 0.0208 (8) | −0.0027 (6) | −0.0023 (7) | 0.0005 (6) |
C73 | 0.0217 (11) | 0.0185 (11) | 0.0245 (12) | 0.0013 (9) | −0.0015 (9) | −0.0007 (9) |
C74 | 0.0217 (12) | 0.0331 (14) | 0.0308 (13) | 0.0052 (11) | 0.0073 (10) | 0.0108 (11) |
C75 | 0.0218 (14) | 0.0382 (16) | 0.082 (2) | −0.0025 (12) | 0.0059 (14) | 0.0021 (15) |
C76 | 0.0244 (12) | 0.0361 (14) | 0.0271 (12) | 0.0054 (11) | 0.0045 (10) | −0.0015 (11) |
N81 | 0.0259 (10) | 0.0102 (9) | 0.0159 (9) | 0.0014 (8) | 0.0009 (8) | −0.0003 (7) |
C81 | 0.0263 (12) | 0.0158 (11) | 0.0135 (10) | 0.0024 (9) | −0.0004 (9) | 0.0001 (8) |
C82 | 0.0212 (11) | 0.0147 (11) | 0.0137 (10) | 0.0032 (9) | −0.0025 (8) | 0.0022 (8) |
O82 | 0.0250 (8) | 0.0149 (8) | 0.0193 (7) | 0.0000 (6) | 0.0007 (6) | −0.0034 (6) |
C83 | 0.0267 (12) | 0.0257 (13) | 0.0259 (12) | 0.0023 (10) | −0.0007 (10) | −0.0051 (10) |
C84 | 0.0275 (13) | 0.0255 (13) | 0.0310 (13) | 0.0028 (10) | 0.0041 (11) | −0.0003 (10) |
C85 | 0.0244 (12) | 0.0253 (12) | 0.0299 (12) | 0.0062 (10) | 0.0044 (10) | 0.0014 (10) |
C86 | 0.0300 (15) | 0.0425 (17) | 0.081 (2) | −0.0067 (13) | 0.0139 (16) | −0.0185 (16) |
N91 | 0.0264 (10) | 0.0147 (9) | 0.0197 (9) | −0.0018 (8) | 0.0052 (8) | −0.0056 (7) |
C91 | 0.0253 (12) | 0.0166 (11) | 0.0175 (11) | −0.0018 (9) | 0.0056 (9) | −0.0020 (9) |
C92 | 0.0204 (11) | 0.0184 (11) | 0.0165 (11) | −0.0029 (9) | 0.0038 (9) | 0.0004 (9) |
O92 | 0.0299 (9) | 0.0265 (9) | 0.0187 (8) | −0.0011 (7) | −0.0017 (7) | 0.0000 (6) |
C93 | 0.0276 (12) | 0.0211 (12) | 0.0257 (12) | −0.0065 (10) | 0.0065 (10) | −0.0029 (9) |
C94 | 0.0219 (11) | 0.0194 (12) | 0.0235 (11) | −0.0063 (9) | 0.0032 (9) | −0.0008 (9) |
C95 | 0.0351 (14) | 0.0241 (13) | 0.0306 (13) | 0.0070 (11) | 0.0090 (11) | 0.0060 (10) |
C96 | 0.0342 (14) | 0.0362 (14) | 0.0234 (12) | 0.0050 (11) | 0.0036 (11) | 0.0062 (11) |
C97 | 0.0290 (13) | 0.0297 (13) | 0.0265 (13) | −0.0020 (11) | 0.0093 (10) | −0.0046 (10) |
C98 | 0.0293 (13) | 0.0336 (14) | 0.0376 (14) | 0.0089 (11) | 0.0070 (11) | 0.0020 (11) |
C99 | 0.0269 (13) | 0.0351 (14) | 0.0270 (13) | 0.0032 (11) | 0.0011 (10) | 0.0073 (11) |
N101 | 0.0234 (9) | 0.0127 (9) | 0.0165 (9) | 0.0008 (8) | 0.0025 (7) | 0.0006 (7) |
C101 | 0.0246 (11) | 0.0143 (11) | 0.0221 (11) | 0.0028 (9) | 0.0059 (9) | 0.0016 (9) |
C102 | 0.0228 (11) | 0.0152 (12) | 0.0177 (10) | 0.0019 (9) | −0.0001 (9) | 0.0011 (9) |
O102 | 0.0368 (9) | 0.0148 (8) | 0.0296 (9) | 0.0055 (7) | 0.0109 (7) | 0.0026 (7) |
C103 | 0.0411 (14) | 0.0197 (12) | 0.0235 (12) | 0.0032 (10) | 0.0129 (11) | −0.0006 (9) |
C104 | 0.0424 (14) | 0.0200 (12) | 0.0174 (11) | −0.0076 (11) | 0.0039 (10) | −0.0022 (9) |
O104 | 0.0434 (11) | 0.0309 (10) | 0.0290 (9) | −0.0158 (8) | −0.0058 (8) | 0.0015 (7) |
C105 | 0.0276 (12) | 0.0184 (11) | 0.0165 (10) | −0.0027 (9) | −0.0002 (9) | 0.0005 (9) |
O1W—H1 | 0.861 (2) | C55—H55A | 0.9700 |
O1W—H2 | 0.929 (2) | C55—H55B | 0.9700 |
N11—C102 | 1.335 (3) | N61—C61 | 1.453 (3) |
N11—C11 | 1.461 (3) | N61—H61 | 0.8600 |
N11—H11 | 0.8600 | C61—C62 | 1.522 (3) |
C11—C12 | 1.529 (3) | C61—C63 | 1.556 (3) |
C11—C13 | 1.537 (3) | C61—H61A | 0.9800 |
C11—H11A | 0.9800 | C62—O62 | 1.244 (3) |
C12—O12 | 1.237 (3) | C62—N71 | 1.333 (3) |
C12—N21 | 1.347 (3) | C63—C64 | 1.523 (3) |
C13—C14 | 1.526 (3) | C63—C65 | 1.525 (3) |
C13—C15 | 1.523 (3) | C63—H63 | 0.9800 |
C13—H13 | 0.9800 | C64—H64A | 0.9600 |
C14—H14A | 0.9600 | C64—H64B | 0.9600 |
C14—H14B | 0.9600 | C64—H64C | 0.9600 |
C14—H14C | 0.9600 | C65—H65A | 0.9600 |
C15—H15A | 0.9600 | C65—H65B | 0.9600 |
C15—H15B | 0.9600 | C65—H65C | 0.9600 |
C15—H15C | 0.9600 | N71—C71 | 1.470 (3) |
N21—C21 | 1.456 (3) | N71—H71 | 0.8600 |
N21—H21 | 0.8600 | C71—C72 | 1.517 (3) |
C21—C22 | 1.526 (3) | C71—C73 | 1.533 (3) |
C21—C23 | 1.525 (3) | C71—H71A | 0.9800 |
C21—H21A | 0.9800 | C72—O72 | 1.236 (3) |
C22—O22 | 1.234 (3) | C72—N81 | 1.337 (3) |
C22—N31 | 1.343 (3) | C73—C74 | 1.534 (3) |
C23—C24 | 1.534 (3) | C73—H73A | 0.9700 |
C23—H23A | 0.9700 | C73—H73B | 0.9700 |
C23—H23B | 0.9700 | C74—C76 | 1.521 (4) |
C24—C25 | 1.528 (3) | C74—C75 | 1.527 (4) |
C24—C26 | 1.523 (3) | C74—H74 | 0.9800 |
C24—H24 | 0.9800 | C75—H75A | 0.9600 |
C25—H25A | 0.9600 | C75—H75B | 0.9600 |
C25—H25B | 0.9600 | C75—H75C | 0.9600 |
C25—H25C | 0.9600 | C76—H76A | 0.9600 |
C26—H26A | 0.9600 | C76—H76B | 0.9600 |
C26—H26B | 0.9600 | C76—H76C | 0.9600 |
C26—H26C | 0.9600 | N81—C81 | 1.460 (3) |
N31—C31 | 1.451 (3) | N81—H81 | 0.8600 |
N31—H31 | 0.8600 | C81—C83 | 1.527 (3) |
C31—C32 | 1.520 (3) | C81—C82 | 1.534 (3) |
C31—C33 | 1.535 (3) | C81—H81A | 0.9800 |
C31—H31A | 0.9800 | C82—O82 | 1.231 (3) |
C32—O32 | 1.227 (3) | C82—N91 | 1.341 (3) |
C32—N41 | 1.351 (3) | C83—C84 | 1.526 (3) |
C33—C34 | 1.529 (4) | C83—H83A | 0.9700 |
C33—H33A | 0.9700 | C83—H83B | 0.9700 |
C33—H33B | 0.9700 | C84—C85 | 1.518 (3) |
C34—C36 | 1.525 (4) | C84—C86 | 1.525 (4) |
C34—C35 | 1.524 (4) | C84—H84 | 0.9800 |
C34—H34 | 0.9800 | C85—H85A | 0.9600 |
C35—H35A | 0.9600 | C85—H85B | 0.9600 |
C35—H35B | 0.9600 | C85—H85C | 0.9600 |
C35—H35C | 0.9600 | C86—H86A | 0.9600 |
C36—H36A | 0.9600 | C86—H86B | 0.9600 |
C36—H36B | 0.9600 | C86—H86C | 0.9600 |
C36—H36C | 0.9600 | N91—C91 | 1.464 (3) |
N41—C41 | 1.467 (3) | N91—H91 | 0.8600 |
N41—H41 | 0.8600 | C91—C93 | 1.534 (3) |
C41—C42 | 1.533 (3) | C91—C92 | 1.535 (3) |
C41—C43 | 1.535 (3) | C91—H91A | 0.9800 |
C41—H41A | 0.9800 | C92—O92 | 1.228 (3) |
C42—O42 | 1.232 (3) | C92—N101 | 1.350 (3) |
C42—N51 | 1.347 (3) | C93—C94 | 1.511 (3) |
C43—C44 | 1.510 (3) | C93—H93A | 0.9700 |
C43—H43A | 0.9700 | C93—H93B | 0.9700 |
C43—H43B | 0.9700 | C94—C99 | 1.383 (4) |
C44—C49 | 1.385 (4) | C94—C95 | 1.389 (3) |
C44—C45 | 1.396 (3) | C95—C96 | 1.380 (4) |
C45—C46 | 1.380 (4) | C95—H95 | 0.9300 |
C45—H45 | 0.9300 | C96—C97 | 1.379 (4) |
C46—C47 | 1.379 (4) | C96—H96 | 0.9300 |
C46—H46 | 0.9300 | C97—C98 | 1.381 (4) |
C47—C48 | 1.380 (4) | C97—H97 | 0.9300 |
C47—H47 | 0.9300 | C98—C99 | 1.386 (4) |
C48—C49 | 1.395 (4) | C98—H98 | 0.9300 |
C48—H48 | 0.9300 | C99—H99 | 0.9300 |
C49—H49 | 0.9300 | N101—C101 | 1.469 (3) |
N51—C51 | 1.470 (3) | N101—C105 | 1.480 (3) |
N51—C55 | 1.479 (3) | C101—C103 | 1.532 (3) |
C51—C52 | 1.532 (3) | C101—C102 | 1.537 (3) |
C51—C53 | 1.536 (3) | C101—H101 | 0.9800 |
C51—H51 | 0.9800 | C102—O102 | 1.235 (3) |
C52—O52 | 1.225 (3) | C103—C104 | 1.514 (4) |
C52—N61 | 1.342 (3) | C103—H10A | 0.9700 |
C53—C54 | 1.518 (3) | C103—H10B | 0.9700 |
C53—H53A | 0.9700 | C104—O104 | 1.422 (3) |
C53—H53B | 0.9700 | C104—C105 | 1.519 (3) |
C54—O54 | 1.423 (3) | C104—H104 | 0.9800 |
C54—C55 | 1.517 (3) | O104—H10C | 0.8200 |
C54—H54 | 0.9800 | C105—H10D | 0.9700 |
O54—H54A | 0.8200 | C105—H10E | 0.9700 |
H1—O1W—H2 | 96.0 (2) | C52—N61—C61 | 122.77 (17) |
C102—N11—C11 | 121.32 (17) | C52—N61—H61 | 118.6 |
C102—N11—H11 | 119.3 | C61—N61—H61 | 118.6 |
C11—N11—H11 | 119.3 | N61—C61—C62 | 107.33 (17) |
N11—C11—C12 | 109.86 (17) | N61—C61—C63 | 110.92 (17) |
N11—C11—C13 | 112.41 (17) | C62—C61—C63 | 112.29 (17) |
C12—C11—C13 | 109.36 (17) | N61—C61—H61A | 108.7 |
N11—C11—H11A | 108.4 | C62—C61—H61A | 108.7 |
C12—C11—H11A | 108.4 | C63—C61—H61A | 108.7 |
C13—C11—H11A | 108.4 | O62—C62—N71 | 124.00 (19) |
O12—C12—N21 | 122.92 (19) | O62—C62—C61 | 121.14 (18) |
O12—C12—C11 | 121.97 (19) | N71—C62—C61 | 114.86 (18) |
N21—C12—C11 | 115.07 (17) | C64—C63—C65 | 110.6 (2) |
C14—C13—C15 | 111.0 (2) | C64—C63—C61 | 111.72 (19) |
C14—C13—C11 | 110.01 (18) | C65—C63—C61 | 113.64 (19) |
C15—C13—C11 | 110.36 (18) | C64—C63—H63 | 106.8 |
C14—C13—H13 | 108.5 | C65—C63—H63 | 106.8 |
C15—C13—H13 | 108.5 | C61—C63—H63 | 106.8 |
C11—C13—H13 | 108.5 | C63—C64—H64A | 109.5 |
C13—C14—H14A | 109.5 | C63—C64—H64B | 109.5 |
C13—C14—H14B | 109.5 | H64A—C64—H64B | 109.5 |
H14A—C14—H14B | 109.5 | C63—C64—H64C | 109.5 |
C13—C14—H14C | 109.5 | H64A—C64—H64C | 109.5 |
H14A—C14—H14C | 109.5 | H64B—C64—H64C | 109.5 |
H14B—C14—H14C | 109.5 | C63—C65—H65A | 109.5 |
C13—C15—H15A | 109.5 | C63—C65—H65B | 109.5 |
C13—C15—H15B | 109.5 | H65A—C65—H65B | 109.5 |
H15A—C15—H15B | 109.5 | C63—C65—H65C | 109.5 |
C13—C15—H15C | 109.5 | H65A—C65—H65C | 109.5 |
H15A—C15—H15C | 109.5 | H65B—C65—H65C | 109.5 |
H15B—C15—H15C | 109.5 | C62—N71—C71 | 124.14 (17) |
C12—N21—C21 | 122.86 (17) | C62—N71—H71 | 117.9 |
C12—N21—H21 | 118.6 | C71—N71—H71 | 117.9 |
C21—N21—H21 | 118.6 | N71—C71—C72 | 106.17 (16) |
N21—C21—C22 | 107.83 (17) | N71—C71—C73 | 110.53 (17) |
N21—C21—C23 | 110.62 (17) | C72—C71—C73 | 110.64 (18) |
C22—C21—C23 | 109.13 (17) | N71—C71—H71A | 109.8 |
N21—C21—H21A | 109.7 | C72—C71—H71A | 109.8 |
C22—C21—H21A | 109.7 | C73—C71—H71A | 109.8 |
C23—C21—H21A | 109.7 | O72—C72—N81 | 124.11 (19) |
O22—C22—N31 | 122.5 (2) | O72—C72—C71 | 119.74 (18) |
O22—C22—C21 | 120.84 (19) | N81—C72—C71 | 116.15 (18) |
N31—C22—C21 | 116.66 (18) | C74—C73—C71 | 115.93 (19) |
C21—C23—C24 | 115.04 (18) | C74—C73—H73A | 108.3 |
C21—C23—H23A | 108.5 | C71—C73—H73A | 108.3 |
C24—C23—H23A | 108.5 | C74—C73—H73B | 108.3 |
C21—C23—H23B | 108.5 | C71—C73—H73B | 108.3 |
C24—C23—H23B | 108.5 | H73A—C73—H73B | 107.4 |
H23A—C23—H23B | 107.5 | C76—C74—C75 | 110.0 (2) |
C25—C24—C26 | 110.40 (19) | C76—C74—C73 | 112.6 (2) |
C25—C24—C23 | 112.11 (18) | C75—C74—C73 | 108.6 (2) |
C26—C24—C23 | 110.44 (19) | C76—C74—H74 | 108.5 |
C25—C24—H24 | 107.9 | C75—C74—H74 | 108.5 |
C26—C24—H24 | 107.9 | C73—C74—H74 | 108.5 |
C23—C24—H24 | 107.9 | C74—C75—H75A | 109.5 |
C24—C25—H25A | 109.5 | C74—C75—H75B | 109.5 |
C24—C25—H25B | 109.5 | H75A—C75—H75B | 109.5 |
H25A—C25—H25B | 109.5 | C74—C75—H75C | 109.5 |
C24—C25—H25C | 109.5 | H75A—C75—H75C | 109.5 |
H25A—C25—H25C | 109.5 | H75B—C75—H75C | 109.5 |
H25B—C25—H25C | 109.5 | C74—C76—H76A | 109.5 |
C24—C26—H26A | 109.5 | C74—C76—H76B | 109.5 |
C24—C26—H26B | 109.5 | H76A—C76—H76B | 109.5 |
H26A—C26—H26B | 109.5 | C74—C76—H76C | 109.5 |
C24—C26—H26C | 109.5 | H76A—C76—H76C | 109.5 |
H26A—C26—H26C | 109.5 | H76B—C76—H76C | 109.5 |
H26B—C26—H26C | 109.5 | C72—N81—C81 | 122.30 (17) |
C22—N31—C31 | 121.04 (18) | C72—N81—H81 | 118.8 |
C22—N31—H31 | 119.5 | C81—N81—H81 | 118.8 |
C31—N31—H31 | 119.5 | N81—C81—C83 | 111.26 (19) |
N31—C31—C32 | 113.39 (19) | N81—C81—C82 | 107.17 (17) |
N31—C31—C33 | 111.85 (18) | C83—C81—C82 | 110.20 (18) |
C32—C31—C33 | 109.76 (18) | N81—C81—H81A | 109.4 |
N31—C31—H31A | 107.2 | C83—C81—H81A | 109.4 |
C32—C31—H31A | 107.2 | C82—C81—H81A | 109.4 |
C33—C31—H31A | 107.2 | O82—C82—N91 | 122.54 (19) |
O32—C32—N41 | 122.4 (2) | O82—C82—C81 | 121.00 (19) |
O32—C32—C31 | 120.2 (2) | N91—C82—C81 | 116.46 (18) |
N41—C32—C31 | 117.34 (19) | C84—C83—C81 | 115.4 (2) |
C34—C33—C31 | 113.7 (2) | C84—C83—H83A | 108.4 |
C34—C33—H33A | 108.8 | C81—C83—H83A | 108.4 |
C31—C33—H33A | 108.8 | C84—C83—H83B | 108.4 |
C34—C33—H33B | 108.8 | C81—C83—H83B | 108.4 |
C31—C33—H33B | 108.8 | H83A—C83—H83B | 107.5 |
H33A—C33—H33B | 107.7 | C85—C84—C86 | 110.6 (2) |
C36—C34—C35 | 111.0 (2) | C85—C84—C83 | 112.5 (2) |
C36—C34—C33 | 111.6 (2) | C86—C84—C83 | 109.6 (2) |
C35—C34—C33 | 109.8 (2) | C85—C84—H84 | 108.0 |
C36—C34—H34 | 108.1 | C86—C84—H84 | 108.0 |
C35—C34—H34 | 108.1 | C83—C84—H84 | 108.0 |
C33—C34—H34 | 108.1 | C84—C85—H85A | 109.5 |
C34—C35—H35A | 109.5 | C84—C85—H85B | 109.5 |
C34—C35—H35B | 109.5 | H85A—C85—H85B | 109.5 |
H35A—C35—H35B | 109.5 | C84—C85—H85C | 109.5 |
C34—C35—H35C | 109.5 | H85A—C85—H85C | 109.5 |
H35A—C35—H35C | 109.5 | H85B—C85—H85C | 109.5 |
H35B—C35—H35C | 109.5 | C84—C86—H86A | 109.5 |
C34—C36—H36A | 109.5 | C84—C86—H86B | 109.5 |
C34—C36—H36B | 109.5 | H86A—C86—H86B | 109.5 |
H36A—C36—H36B | 109.5 | C84—C86—H86C | 109.5 |
C34—C36—H36C | 109.5 | H86A—C86—H86C | 109.5 |
H36A—C36—H36C | 109.5 | H86B—C86—H86C | 109.5 |
H36B—C36—H36C | 109.5 | C82—N91—C91 | 119.13 (18) |
C32—N41—C41 | 120.91 (19) | C82—N91—H91 | 120.4 |
C32—N41—H41 | 119.5 | C91—N91—H91 | 120.4 |
C41—N41—H41 | 119.5 | N91—C91—C93 | 111.04 (18) |
N41—C41—C42 | 107.27 (17) | N91—C91—C92 | 109.25 (17) |
N41—C41—C43 | 111.62 (18) | C93—C91—C92 | 109.61 (19) |
C42—C41—C43 | 113.01 (19) | N91—C91—H91A | 109.0 |
N41—C41—H41A | 108.3 | C93—C91—H91A | 109.0 |
C42—C41—H41A | 108.3 | C92—C91—H91A | 109.0 |
C43—C41—H41A | 108.3 | O92—C92—N101 | 122.6 (2) |
O42—C42—N51 | 122.8 (2) | O92—C92—C91 | 120.03 (19) |
O42—C42—C41 | 120.9 (2) | N101—C92—C91 | 117.40 (18) |
N51—C42—C41 | 116.14 (19) | C94—C93—C91 | 109.31 (18) |
C44—C43—C41 | 113.70 (19) | C94—C93—H93A | 109.8 |
C44—C43—H43A | 108.8 | C91—C93—H93A | 109.8 |
C41—C43—H43A | 108.8 | C94—C93—H93B | 109.8 |
C44—C43—H43B | 108.8 | C91—C93—H93B | 109.8 |
C41—C43—H43B | 108.8 | H93A—C93—H93B | 108.3 |
H43A—C43—H43B | 107.7 | C99—C94—C95 | 118.2 (2) |
C49—C44—C45 | 118.2 (2) | C99—C94—C93 | 121.8 (2) |
C49—C44—C43 | 121.8 (2) | C95—C94—C93 | 119.8 (2) |
C45—C44—C43 | 119.9 (2) | C96—C95—C94 | 121.5 (2) |
C46—C45—C44 | 121.0 (2) | C96—C95—H95 | 119.3 |
C46—C45—H45 | 119.5 | C94—C95—H95 | 119.3 |
C44—C45—H45 | 119.5 | C97—C96—C95 | 119.9 (2) |
C47—C46—C45 | 120.1 (2) | C97—C96—H96 | 120.0 |
C47—C46—H46 | 120.0 | C95—C96—H96 | 120.0 |
C45—C46—H46 | 120.0 | C96—C97—C98 | 119.2 (2) |
C46—C47—C48 | 120.0 (2) | C96—C97—H97 | 120.4 |
C46—C47—H47 | 120.0 | C98—C97—H97 | 120.4 |
C48—C47—H47 | 120.0 | C99—C98—C97 | 120.7 (2) |
C47—C48—C49 | 119.8 (2) | C99—C98—H98 | 119.6 |
C47—C48—H48 | 120.1 | C97—C98—H98 | 119.6 |
C49—C48—H48 | 120.1 | C98—C99—C94 | 120.4 (2) |
C44—C49—C48 | 120.9 (2) | C98—C99—H99 | 119.8 |
C44—C49—H49 | 119.6 | C94—C99—H99 | 119.8 |
C48—C49—H49 | 119.6 | C92—N101—C101 | 120.82 (18) |
C42—N51—C51 | 121.53 (18) | C92—N101—C105 | 126.31 (18) |
C42—N51—C55 | 126.41 (17) | C101—N101—C105 | 112.01 (17) |
C51—N51—C55 | 111.87 (17) | N101—C101—C103 | 102.41 (17) |
N51—C51—C52 | 113.54 (17) | N101—C101—C102 | 115.58 (18) |
N51—C51—C53 | 102.61 (17) | C103—C101—C102 | 112.72 (19) |
C52—C51—C53 | 111.69 (18) | N101—C101—H101 | 108.6 |
N51—C51—H51 | 109.6 | C103—C101—H101 | 108.6 |
C52—C51—H51 | 109.6 | C102—C101—H101 | 108.6 |
C53—C51—H51 | 109.6 | O102—C102—N11 | 123.5 (2) |
O52—C52—N61 | 123.70 (19) | O102—C102—C101 | 118.23 (19) |
O52—C52—C51 | 119.59 (19) | N11—C102—C101 | 118.06 (18) |
N61—C52—C51 | 116.70 (18) | C104—C103—C101 | 103.49 (18) |
C54—C53—C51 | 103.58 (17) | C104—C103—H10A | 111.1 |
C54—C53—H53A | 111.0 | C101—C103—H10A | 111.1 |
C51—C53—H53A | 111.0 | C104—C103—H10B | 111.1 |
C54—C53—H53B | 111.0 | C101—C103—H10B | 111.1 |
C51—C53—H53B | 111.0 | H10A—C103—H10B | 109.0 |
H53A—C53—H53B | 109.0 | O104—C104—C103 | 107.80 (19) |
O54—C54—C53 | 111.53 (18) | O104—C104—C105 | 110.4 (2) |
O54—C54—C55 | 107.69 (17) | C103—C104—C105 | 103.72 (19) |
C53—C54—C55 | 103.94 (18) | O104—C104—H104 | 111.5 |
O54—C54—H54 | 111.1 | C103—C104—H104 | 111.5 |
C53—C54—H54 | 111.1 | C105—C104—H104 | 111.5 |
C55—C54—H54 | 111.1 | C104—O104—H10C | 109.5 |
C54—O54—H54A | 109.5 | N101—C105—C104 | 103.25 (17) |
N51—C55—C54 | 103.83 (17) | N101—C105—H10D | 111.1 |
N51—C55—H55A | 111.0 | C104—C105—H10D | 111.1 |
C54—C55—H55A | 111.0 | N101—C105—H10E | 111.1 |
N51—C55—H55B | 111.0 | C104—C105—H10E | 111.1 |
C54—C55—H55B | 111.0 | H10D—C105—H10E | 109.1 |
H55A—C55—H55B | 109.0 | ||
C102—N11—C11—C12 | −128.7 (2) | C52—N61—C61—C62 | −153.20 (19) |
C102—N11—C11—C13 | 109.3 (2) | C52—N61—C61—C63 | 83.8 (2) |
N11—C11—C12—O12 | −64.0 (3) | N61—C61—C62—O62 | −34.2 (3) |
C13—C11—C12—O12 | 59.8 (3) | C63—C61—C62—O62 | 88.0 (2) |
N11—C11—C12—N21 | 118.24 (19) | N61—C61—C62—N71 | 146.40 (17) |
C13—C11—C12—N21 | −117.9 (2) | C63—C61—C62—N71 | −91.5 (2) |
N11—C11—C13—C14 | −61.0 (2) | N61—C61—C63—C64 | −168.15 (18) |
C12—C11—C13—C14 | 176.71 (17) | C62—C61—C63—C64 | 71.8 (2) |
N11—C11—C13—C15 | 176.21 (18) | N61—C61—C63—C65 | 65.9 (2) |
C12—C11—C13—C15 | 53.9 (2) | C62—C61—C63—C65 | −54.2 (2) |
O12—C12—N21—C21 | −7.4 (3) | O62—C62—N71—C71 | −8.1 (3) |
C11—C12—N21—C21 | 170.28 (19) | C61—C62—N71—C71 | 171.34 (18) |
C12—N21—C21—C22 | −99.6 (2) | C62—N71—C71—C72 | −122.5 (2) |
C12—N21—C21—C23 | 141.16 (19) | C62—N71—C71—C73 | 117.4 (2) |
N21—C21—C22—O22 | −64.1 (2) | N71—C71—C72—O72 | −57.6 (2) |
C23—C21—C22—O22 | 56.1 (2) | C73—C71—C72—O72 | 62.4 (2) |
N21—C21—C22—N31 | 117.00 (19) | N71—C71—C72—N81 | 121.62 (19) |
C23—C21—C22—N31 | −122.8 (2) | C73—C71—C72—N81 | −118.4 (2) |
N21—C21—C23—C24 | 173.98 (17) | N71—C71—C73—C74 | 172.01 (18) |
C22—C21—C23—C24 | 55.5 (2) | C72—C71—C73—C74 | 54.7 (3) |
C21—C23—C24—C25 | 65.1 (3) | C71—C73—C74—C76 | 61.5 (3) |
C21—C23—C24—C26 | −171.29 (19) | C71—C73—C74—C75 | −176.5 (2) |
O22—C22—N31—C31 | −2.3 (3) | O72—C72—N81—C81 | −0.2 (3) |
C21—C22—N31—C31 | 176.57 (19) | C71—C72—N81—C81 | −179.37 (18) |
C22—N31—C31—C32 | −95.4 (2) | C72—N81—C81—C83 | 117.2 (2) |
C22—N31—C31—C33 | 139.8 (2) | C72—N81—C81—C82 | −122.3 (2) |
N31—C31—C32—O32 | 152.7 (2) | N81—C81—C82—O82 | −88.0 (2) |
C33—C31—C32—O32 | −81.4 (3) | C83—C81—C82—O82 | 33.2 (3) |
N31—C31—C32—N41 | −30.0 (3) | N81—C81—C82—N91 | 91.1 (2) |
C33—C31—C32—N41 | 95.9 (2) | C83—C81—C82—N91 | −147.7 (2) |
N31—C31—C33—C34 | −62.2 (3) | N81—C81—C83—C84 | −59.5 (3) |
C32—C31—C33—C34 | 171.1 (2) | C82—C81—C83—C84 | −178.24 (19) |
C31—C33—C34—C36 | −55.8 (3) | C81—C83—C84—C85 | −58.9 (3) |
C31—C33—C34—C35 | −179.4 (2) | C81—C83—C84—C86 | 177.7 (2) |
O32—C32—N41—C41 | −6.6 (3) | O82—C82—N91—C91 | −1.3 (3) |
C31—C32—N41—C41 | 176.13 (19) | C81—C82—N91—C91 | 179.68 (18) |
C32—N41—C41—C42 | 139.7 (2) | C82—N91—C91—C93 | 175.07 (19) |
C32—N41—C41—C43 | −96.0 (2) | C82—N91—C91—C92 | 54.1 (3) |
N41—C41—C42—O42 | 104.7 (2) | N91—C91—C92—O92 | 56.2 (3) |
C43—C41—C42—O42 | −18.8 (3) | C93—C91—C92—O92 | −65.7 (3) |
N41—C41—C42—N51 | −71.0 (2) | N91—C91—C92—N101 | −124.2 (2) |
C43—C41—C42—N51 | 165.56 (18) | C93—C91—C92—N101 | 113.9 (2) |
N41—C41—C43—C44 | 151.11 (19) | N91—C91—C93—C94 | 166.69 (18) |
C42—C41—C43—C44 | −87.9 (2) | C92—C91—C93—C94 | −72.5 (2) |
C41—C43—C44—C49 | 116.3 (3) | C91—C93—C94—C99 | 88.8 (3) |
C41—C43—C44—C45 | −65.2 (3) | C91—C93—C94—C95 | −86.1 (3) |
C49—C44—C45—C46 | 0.8 (3) | C99—C94—C95—C96 | −0.6 (4) |
C43—C44—C45—C46 | −177.7 (2) | C93—C94—C95—C96 | 174.5 (2) |
C44—C45—C46—C47 | −0.5 (4) | C94—C95—C96—C97 | −0.7 (4) |
C45—C46—C47—C48 | 0.0 (4) | C95—C96—C97—C98 | 1.4 (4) |
C46—C47—C48—C49 | 0.3 (4) | C96—C97—C98—C99 | −0.9 (4) |
C45—C44—C49—C48 | −0.5 (4) | C97—C98—C99—C94 | −0.5 (4) |
C43—C44—C49—C48 | 178.0 (2) | C95—C94—C99—C98 | 1.1 (4) |
C47—C48—C49—C44 | −0.1 (4) | C93—C94—C99—C98 | −173.8 (2) |
O42—C42—N51—C51 | −0.8 (3) | O92—C92—N101—C101 | 4.2 (3) |
C41—C42—N51—C51 | 174.80 (17) | C91—C92—N101—C101 | −175.37 (18) |
O42—C42—N51—C55 | 173.8 (2) | O92—C92—N101—C105 | 172.8 (2) |
C41—C42—N51—C55 | −10.6 (3) | C91—C92—N101—C105 | −6.8 (3) |
C42—N51—C51—C52 | −79.5 (2) | C92—N101—C101—C103 | 155.1 (2) |
C55—N51—C51—C52 | 105.2 (2) | C105—N101—C101—C103 | −15.0 (2) |
C42—N51—C51—C53 | 159.77 (19) | C92—N101—C101—C102 | −82.0 (3) |
C55—N51—C51—C53 | −15.5 (2) | C105—N101—C101—C102 | 108.0 (2) |
N51—C51—C52—O52 | 176.52 (19) | C11—N11—C102—O102 | −1.9 (3) |
C53—C51—C52—O52 | −68.0 (3) | C11—N11—C102—C101 | 173.09 (19) |
N51—C51—C52—N61 | −2.3 (3) | N101—C101—C102—O102 | −166.9 (2) |
C53—C51—C52—N61 | 113.2 (2) | C103—C101—C102—O102 | −49.6 (3) |
N51—C51—C53—C54 | 32.5 (2) | N101—C101—C102—N11 | 17.8 (3) |
C52—C51—C53—C54 | −89.4 (2) | C103—C101—C102—N11 | 135.1 (2) |
C51—C53—C54—O54 | 77.8 (2) | N101—C101—C103—C104 | 33.0 (2) |
C51—C53—C54—C55 | −38.0 (2) | C102—C101—C103—C104 | −91.8 (2) |
C42—N51—C55—C54 | 177.27 (19) | C101—C103—C104—O104 | 77.7 (2) |
C51—N51—C55—C54 | −7.7 (2) | C101—C103—C104—C105 | −39.4 (2) |
O54—C54—C55—N51 | −90.3 (2) | C92—N101—C105—C104 | −178.4 (2) |
C53—C54—C55—N51 | 28.1 (2) | C101—N101—C105—C104 | −9.0 (2) |
O52—C52—N61—C61 | 4.2 (3) | O104—C104—C105—N101 | −85.6 (2) |
C51—C52—N61—C61 | −177.09 (18) | C103—C104—C105—N101 | 29.7 (2) |
D—H···A | H···A | D···A | D—H···A |
N11—H11···O82 | 2.19 | 3.012 (2) | 159 |
N31—H31···O62 | 2.19 | 2.985 (2) | 155 |
N81—H81···O12 | 1.98 | 2.831 (2) | 173 |
N21—H21···O72i | 2.03 | 2.870 (2) | 164 |
O54—H54A···O42ii | 1.94 | 2.759 (2) | 177 |
N71—H71···O102iii | 2.16 | 3.000 (2) | 166 |
N91—H91···O22iii | 2.13 | 2.949 (2) | 159 |
O104—H10C···O32iv | 2.01 | 2.823 (3) | 170 |
O1W—H1···O54 | 2.03 | 2.870 (3) | 163 |
O1W—H2···O52ii | 2.12 | 2.950 (3) | 148 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, −z+1; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+3/2, −y+1, z+1/2. |
D—H···A | H···A | D···A | D—H···A |
4 | |||
β-sheet | |||
N31—H31···O62 | 2.01 | 2.838 (5) | 162 |
N61—H61···O32 | 2.22 | 3.048 (5) | 160 |
N81—H81···O12 | 2.19 | 2.905 (4) | 140 |
Intermolecular | |||
N21—H21···O52i | 2.25 | 3.090 (4) | 165 |
N41—H41···O72i | 2.13 | 2.966 (5) | 165 |
N71—H71···O22ii | 1.97 | 2.818 (4) | 168 |
O104—H10E···O102iii | 2.06 | 2.869 (5) | 168 |
Solvents relating | |||
O54—H54···O2M | 1.99 | 2.725 (9) | 149 |
O1W—H2W···O54 | 2.01 | 2.847 (7) | 163 |
O1W—H1W···O102ii | 2.03 | 2.927 (6) | 178 |
O1M—H1M···O42 | 2.03 | 2.831 (5) | 166 |
O2M—H2MA···O82iv | 1.99 | 2.727 (8) | 144 |
5 | |||
β-sheet | |||
N11—H11···O82 | 2.19 | 3.012 (2) | 159 |
N31—H31···O62 | 2.19 | 2.985 (2) | 155 |
N81—H81···O12 | 1.98 | 2.831 (2) | 173 |
Intermolecular | |||
N21—H21···O72v | 2.03 | 2.870 (2) | 164 |
O54—H54A···O42vi | 1.94 | 2.759 (2) | 177 |
N71—H71···O102vii | 2.16 | 3.000 (2) | 166 |
N91—H91···O22vii | 2.13 | 2.949 (2) | 159 |
O104—H10C···O32viii | 2.01 | 2.823 (3) | 170 |
Solvent relating | |||
O1W—H1···O54 | 2.03 | 2.870 (3) | 163 |
O1W—H2···O52vi | 2.12 | 2.950 (3) | 148 |
Symmetry codes: (i) -x + 1; y + 1/2, -z + 1/2; (ii) -x + 1, y - 1/2, -z + 1/2; (iii) x + 1/2, -y + 3/2, -z + 1; (iv) -x + 3/2, -y + 1, z - 1/2; (v) -x + 1, y + 1/2, -z + 3/2; (vi) x + 1/2, -y + 1/2, -z + 1; (vii) -x + 1, y - 1/2, -z + 3/2; (viii) -x + 3/2, -y + 1, z + 1/2. |
Residue | 4 | 5 | ||
φ | ψ | φ | ψ | |
Val1 | -120.8 (4) | 142.0 (3) | -128.7 (2) | 118.2 (2) |
Leu2 | -129.5 (4) | 115.4 (4) | -99.6 (2) | 117.0 (2) |
Leu3 | -120.3 (4) | 97.3 (4) | -95.4 (2) | -30.0 (3) |
D-Phe4 | 56.3 (5)a | -124.7 (4)a | -96.0 (2) | -71.0 (2) |
t/cHyp5 | -82.9 (5)a | 9.2 (6)a | -79.5 (2) | -2.3 (3) |
Val6 | -119.4 (4) | 120.1 (4) | -153.2 (2) | 146.4 (2) |
Leu7 | -98.0 (4) | 107.2 (4) | -122.5 (2) | 121.6 (2) |
Leu8 | -80.4 (5) | -32.5 (5) | -122.3 (2) | 91.1 (2) |
D-Phe9 | 146.8 (4) | -92.4 (4) | 54.1 (3)a | -124.2 (2)a |
t/cHyp10 | -77.2 (5) | -12.4 (5) | -82.0 (3)a | 17.8 (3)a |
Note: (a) The angles are classed to Type II' β-turn, defined as (φ, ψ) = (60, -120)i+1 and (-80, 0)i+2. |
Residue | Q2a | φ2a | χ1 | χ2 | χ3 | χ4 | θ | Type |
4 | ||||||||
tHyp5 | 0.398 (7) | 81.8 (8) | 35.8 (5) | -40.3 (5) | 28.8 (5) | -6.4 (5) | -18.2 (5) | down |
tHyp10 | 0.335 (5) | 81.1 (7) | 30.5 (4) | -34.0 (4) | 24.1 (4) | -5.1 (4) | -16.0 (4) | down |
5 | ||||||||
cHyp5 | 0.369 (2) | 84.1 (3) | 32.5 (2) | -38.0 (2) | 28.1 (2) | -7.7 (2) | -15.5 (2) | down |
cHyp10 | 0.379 (3) | 85.7 (3) | 33.0 (2) | -39.4 (2) | 29.7 (2) | -9.0 (2) | -15.0 (2) | down |
Note: (a) Defined by Cremer & Pople (1975). Puckering parameters were calculated using PLATON (Spek, 2020). |
Compound | Puckering | Structurea | Compound | Puckering | Structurea |
1 | down | s+a | |||
2 | up | a | 4 | down | a |
3 | down | s | 5 | down | a |
Note: (a) The letters `a' and `s' indicate the asymmetric and symmetric peptide rings, respectively. |
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