research papers
Development of a scalar-based geometric parameterization approach for the
landscape of dithienylethene-based crystalline solidsaDepartment of Chemistry, University at Buffalo, State University of New York, Buffalo, NY 14260-3000, USA, and bNSF's ChemMatCARS, University of Chicago, Chicago, Lemont, IL 60439, USA
*Correspondence e-mail: jbb6@buffalo.edu
Dithienylethenes (DTEs) are a promising class of organic photoswitches that can be used to create crystalline solids with properties controlled by light. However, the ability of DTEs to adopt multiple conformations, only one of which is photoactive, complicates the rational design of these materials. Herein, the synthesis and structural characterization of 19 crystalline solids containing a single DTE molecule are described. A novel D–D analysis of the molecular geometries obtained from rotational surface calculations and the ensemble of experimental structures were used to construct a crystal landscape for DTE. Of the 19 crystal structures, 17 contained photoinactive DTE rotamers and only 2 were photoactive. These results highlight the challenges associated with the design of these materials. Overall, the D–D analysis described herein provides rapid, effective and intuitive means of linking the molecular structure to photoactivity that could be applied more broadly to afford a general strategy for producing photoactive diarylethene-based crystalline solids.
Keywords: diarylethene; photoactive; crystal landscapes; crystal engineering; properties of solids; crystal design.
1. Introduction
Crystal engineering is a powerful tool used to design and synthesize new materials with specific physical and chemical properties by exploiting the role that individual intermolecular interactions play when forming crystalline solids (Nangia & Desiraju, 2019). Without a doubt, crystal engineering has been central to the development of crystalline materials tailored for a wide range of chemical applications including pharmaceuticals (Karimi-Jafari et al., 2018; Duggirala et al., 2016; Guo et al., 2021), biosensors (Fu et al., 2023), gas separation and storage (Shekhah et al., 2018; Cheng et al., 2022), and electronics and optics (Kandambeth et al., 2022; Jiang et al., 2021; Dar & Rashid, 2021).
Traditionally, crystal structures are viewed as repeating patterns of atoms, molecules or ions arranged in a three-dimensional lattice. However, a particularly powerful concept in crystal engineering is to instead view the same ). Different crystallizing conditions can lead to the formation of different crystal structures, each with its own unique set of properties. Therefore, it is important to assess a wide variety of crystallizing conditions to produce crystalline solids (Samanta et al., 2021; Tothadi & Desiraju, 2012; Singh et al., 2016; Ranjan et al., 2020; Rajkumar & Desiraju, 2021). Consequently, a wide variety of crystalline solids including polymorphs, hydrates, solvates, co-crystals and metal–organic frameworks can help deepen our understanding of how the molecule of interest is impacted by the surrounding crystalline environment and vice versa. This includes identifying supramolecular synthons and non-covalent interactions that are important in the formation of crystals, which inevitably affects the physical and chemical properties of crystalline solids, such as their solubility and melting point.
as a rich structural landscape in which the position of a molecule in a single crystal is a data point on this landscape (Desiraju, 2021The changing crystalline environments directly impact the molecule of interest and ultimately the functionally important properties of the crystal, including water sorption (Reutzel-Edens & Bhardwaj, 2020), electronic properties (Narayanan et al., 2017; Sun et al., 2019), detonation properties (Landenberger et al., 2015; Kent et al., 2018; Aakeröy et al., 2015b) and thermal stability (Aakeröy et al., 2015a; Angevine et al., 2022b,a) among others. Likewise, photoactivity in the solid state is another property heavily influenced by (Yelgaonkar et al., 2020; Campillo-Alvarado et al., 2020; Borchers et al., 2022).
Dithienylethenes (DTEs) are a promising class of molecules for use in organic solid-state photoswitches. DTEs are attractive because they are solid-state reactive, both isomers are thermally stable and they are fatigue resistant (Fukaminato et al., 2001; Herder et al., 2015; Kitagawa et al., 2013; Kobatake et al., 2000, 2002, 2007; Shibata et al., 2002). However, the rational design process for DTE-based crystalline solids is complicated by their conformational flexibility. The two thiophene rings can rotate around the central ethylene bridge, which gives rise to parallel and anti-parallel rotational isomers (Zhang & Tian, 2018; Rice et al., 2020; Cox et al., 2016). DTE molecules are considered to be potentially photoactive in the solid state when they adopt the antiparallel geometry and have an interatomic distance between the two active carbon atoms of less than 4.2 Å (see infra) (Kobatake et al., 2002). If neither of these conditions are met, the molecule is not expected to be photoactive. That said, the geometry of the DTEs within the crystalline structure profoundly affects their functionality as a photoswitch. Thus, the development and assessment of the landscape for these materials will play a critical role in the rational design of future DTE-based materials with desired molecular geometries.
Herein we report the synthesis of (Z)-1,2-bis(2-methyl-5-(pyridin-4-yl)thiophen-3-yl)-1,2-diphenylethene (DTE), a bulky acyclic DTE molecule with a pyridyl functionalized thiophene pendant groups (Fig. 1). We incorporated DTE into 19 different crystalline solids such as polymorphs, co-crystals, coordination polymers and metal–organic frameworks. Single-crystal X-ray diffraction (SCXRD) analysis revealed that only 2 of the 19 crystal structures contained DTE in the photoactive geometry. These findings led to the development of a novel scalar-based approach to parametrizing the DTE geometry, which may be applied more broadly to this class of photoactive molecules.
2. Methods
2.1. Synthesis and characterization
All reagents were purchased from commercial sources and used as received unless otherwise noted. 1H NMR spectra were obtained on a Varian Inova-400 or Varian Inova-500 operating at 400 and 500 MHz, respectively. 1H NMR peaks are referenced to residual solvent signals in CDCl3 at 7.26 p.p.m. (Gottlieb et al., 1997). SCXRD data were collected on a rotating anode source or using synchrotron radiation. Full details of the synthesis and characterization are provided in the supporting information (Fig. S1) which includes a detailed list of co-formers and linkers used for synthesizing crystals (Fig. S2).
2.2. Nomenclature
Each of the 19 crystal structures comprise one or two crystallographically unique DTEs. The following naming convention will be used to differentiate between these structures and their crystallographically unique DTEs. Each X and labelled DTE-[X]. If DTE-[X] has one crystallographically unique DTE in the DTE itself will be referred to as DTE-X. If DTE-[X] has two crystallographically unique DTEs in the DTE-Xa or DTE-Xb will be used to refer to individual DTEs, while DTE-Xa/b will be used to refer to both DTEs.
is assigned a number2.3. Computational methods
All calculations were performed using density functional theory (DFT) with the computational software suite Gaussian09 (Revision D.01; Frisch et al., 2013). The hybrid functional ωB97X-D with the 6-31G(d) basis set was used for all calculations (Chai & Head-Gordon, 2008). DTE and the methyl-substituted variation were geometry optimized in the anti-active geometry. The vibrational frequencies of each optimized DTE were calculated to verify that each geometry was a true energetic minimum.
Relaxed ΦA[C18, C1, C8, C11] was rotated by ±1° increments creating a clockwise (CW, −1°, negative) or counter-clockwise (CCW, +1°, positive) rotation about the C1—C8 bond (Fig. 1). After each 1° increment, a geometry optimization was performed on the molecule while keeping ΦA rigid. These rotation and geometry optimization processes were performed in succession until all values of ΦA within ±180° were examined for a total of 360°. All resulting energies were converted from Hartree to kcal mol−1.
surface (RPES) scans were performed on the optimized DTE and its methyl-substituted variant. The torsion angleIn addition to ΦA, three other parameters were used to assess the geometries of DTE (Fig. 2): the relative orientation of methyl groups at the active carbon atoms (ΦB), the interatomic distance between the active carbon atoms (Dactive) and the interatomic distance between the methyl carbon atoms bonded to the active carbon atoms (DMe-Me). The relative orientation of methyl groups at the active carbon atoms is defined as the torsion angle ΦB[C12, C11, C28, C29]. Dactive is defined as the interatomic distance between carbon atoms C11 and C28. DMe-Me is defined as the interatomic distance between carbon atoms C12 and C29.
3. Results and discussion
3.1. Summary of crystal structures obtained
A total of 19 DTE-[1–19] single crystals containing DTE were analysed using SCXRD. Two neat crystal structures of DTE (DTE-[1,2]) are polymorphs. Four crystal structures (DTE-[3–6]) are co-crystals with multitopic carboxylic acids. Four crystal structures (DTE-[7–10]) are isostructural coordination polymers with the metals cobalt, nickel, zinc and cadmium. Crystal structures DTE-[11,12] are two unique coordination polymers with copper coordinated to iodine and bromine, respectively. The remaining crystal structures (DTE-[13–19]) were produced from MOF syntheses in which zinc and DTE were solvothermally reacted with various multitopic carboxylic acids. Five of the crystal structures (DTE-[3,4,6,14,15]) possess two crystallographically unique DTEs. Altogether, the present work includes a total of 24 unique DTE geometries arising from 19 crystal structures. By visual inspection, 6 of the molecules (DTE-4a/b,5,6a/b,11) were assigned to the P3/P4 conformation. A total of 16 molecules, DTE-1,2,3a/b,7–10,12,13,14a/b,15a/b,16,17, were assigned the AP2 conformation, and the two remaining molecules, DTE-18,19, were assigned the AP1 conformation. The conformer assignments and structural parameters for the experimental DTE geometries are provided in Table S1 of the supporting information. Additionally, the photoactivity of each was confirmed by irradiating a single crystal with UV light. The single crystal was deemed photoactive if it showed any observable colour change, otherwise it was deemed photoinactive.
3.2. Relaxed scan
The RPES plot for DTE reveals eight energetic minima and eight energetic maxima split evenly between each scan direction [Fig. 3(b)]. The four sets of energetic minima correspond to four discrete conformers: two conformers with antiparallel geometry (DTE-AP1 and DTE-AP2) and two conformers with parallel geometry (DTE-P3 and DTE-P4). Fig. 3(a) depicts each geometry from 2 different perspectives. The orientation of the vectors and characterizes each geometry. The antiparallel geometry is characterized by the two vectors pointing in approximately opposite directions, whereas the parallel geometry occurs when two vectors point in a similar direction.
The torsion angles (ΦA) and energies relative to the lowest-energy conformer DTE-P3 (ΔE) are summarized in Table 1. These four conformers will be used to analyse the conformers observed in the single-crystal structures.
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The DTE-AP1 and DTE-AP2 conformers can be interconverted by rotating each thienyl moiety in the same direction. This concerted rotation of the thienyl moieties results in ΦA increasing from 51.46° for DTE-AP1 to 127.46° for DTE-AP2. Consequently, Dactive also increases during this process from 3.45 Å for DTE-AP1 to 5.19 Å for DTE-AP2. The photoactivity of dithienylethenes is well established and requires the antiparallel geometry and for Dactive to be less than 4.2 Å. Though DTE-AP1 and DTE-AP2 have the correct geometry necessary to be photoactive, only DTE-AP1 is potentially photoactive (Dactive = 3.45 Å). This indicates that Dactive is the most significant distinction in photoactivity between the two antiparallel conformers. The two parallel conformers can be interconverted in a similar way to the two antiparallel conformers. Although Dactive is less than 4.2 Å for the two parallel conformers (DTE-P3 and DTE-P4), their geometry prohibits any photoactivity.
The energy differences between each scan direction are 0.00 kcal mol−1 for DTE-AP1, 0.15 kcal mol−1 for DTE-AP2, 0.00 kcal mol−1 for DTE-P3 and 1.83 kcal mol−1 for DTE-P4. The larger energy difference between each scan direction for DTE-P4 is caused by a difference in the degree of planarity between the pyridyl rings and thiophene rings (Fig. S3).
An RPES scan on a similar molecule in which the pyridyl rings were substituted with methyl groups resulted in no significant scan-dependent differences in energy for any of the conformers (Table S2, Fig. S4). Furthermore, the ΔE values for the two methyl-substituted parallel conformers (P3 and P4) were almost identical at ∼0.36 kcal mol−1. Thus, the DTE-P3 and DTE-P4 conformers will be generally described as a singular species of and labelled DTE-P3/P4.
The increase in energy of each conformer as they approach their respective energetic maximum is caused by an increasingly unfavourable steric interaction between the phenyl rings on the backbone and the methyl group bonded to the active carbon. This interaction is seen as the phenyl rings and methyl groups rotating in a concerted effort to reduce their interaction with each other. Smaller energetic barriers are observed between the anti–anti and para–para rotamers, whereas the larger barriers are observed between the anti–para and para–anti geometries.
3.3. DTE scalar-based parameterization
The DTE conformer type is critically important to the photoactivity of a crystalline solid and has been traditionally assigned by visually inspecting the DTE molecule itself. However, this method can be time-consuming and subjective. To address this issue, we developed a series of DTE parameters (Dactive, DMe-Me and ΦB) that can be quickly calculated and used to unambiguously determine the conformer type and visualize the crystal landscape.
The first parameter, Dactive, provides some information, but it is not enough information to unambiguously determine the type of conformer. As mentioned earlier, the photoactivity of DTE molecules depends on both the molecular geometry and the value of Dactive. DTE molecules with Dactive > 4.2 Å are not expected to be photoactive. However, the photoactivity of DTE molecules with Dactive < 4.2 Å depends on the orientation of thiophene rings. Thus, we attempted to combine Dactive with two different vector-based parameters that represent the orientation of the thiophene rings such as ΦB [Fig. S5(a)]. Since enantiomeric pairs of any given DTE molecule have the same values but opposite signs, we were unable to unambiguously assign rotamers using them [Fig. S5(b)]. Therefore, the parameters for a given DTE conformer may be indistinguishable from those of the of a different conformer [Fig. S5(c)].
The use of scalar-based parameters, namely interatomic distances, eliminates complications arising from the sign of the relative orientation of vectors. Likewise, these values are invariant to structure inversion. In other words, enantiomeric pairs will possess identical values. Therefore, we combined Dactive with another scalar-based parameter DMe-Me to describe the photoactive nature of DTE molecules. When used together, these two parameters describe how the thiophene rings are orientated relative to each other. The plot of DMe-Me versus Dactive for the calculated DTE geometries takes on the shape of a broken ellipse (Fig. 4).
The lowest-energy calculated structures (ΔE < 5 kcal mol−1) for each of the conformers fall into one of three distinct regions. Region I, which contains the lowest-energy AP1 conformers, is characterized by Dactive < DMe-Me and Dactive < 4.20 Å. Region II, where Dactive > DMe-Me and Dactive > 4.20 Å, contains the AP2 conformers. Region III, where Dactive ≃ DMe-Me and Dactive < 5.0 Å, comprises the P3/P4 conformers. Some overlap between regions does exist for the calculated structures. For example, the calculated structures for the two antiparallel conformers are present where 3.70 Å < Dactive < 4.70 Å and 5.20 Å < DMe-Me < 6.70 Å. However, this overlap only occurs for high-energy structures of a given conformer (ΔE > 5 kcal mol−1), and the geometries for which are unlikely to be observed in a crystalline solid.
D–D analysis (Dactive–DMe-Me analysis) of the crystal structures confirmed that the experimental DTE geometries were clustered into the three regions described above. As anticipated, we found that the structures containing the AP1, AP2 and P3/P4 conformers are exclusively located in regions I, II and III, respectively. In fact, it is notable that most of the experimental structures are observed near the lowest-energy calculated structures. Though crystal packing forces may lead to slight deviations from the calculated minimum structures, the observed structures agree well with the minimum energy structures for each conformer type.
4. Conclusions
We found that 17 of the 19 observed DTE crystal structures (89.5%) contained a photoinactive conformer. Of these, 13 included the AP2 rotamer and 4 included the P3/P4 rotamers. The photoactive AP1 rotamer was only observed in 2 of the 19 crystal structures (10.5%). These results highlight the challenges associated with the design and synthesis of functional DTE-based crystalline materials. These challenges can be applied more broadly to any conformationally flexible system in which a specific conformation is desired in the crystalline phase. In the present case, the desired photoactivity is directly linked to the DTE conformation, which is not easily controlled in the crystalline state.
Future work will include higher level computational methods on gas phase and solvated DTE to improve the accuracy of rotamer energies. Periodic calculations using experimental crystal structures will be challenging, as these systems are large and complex. However, these calculations could provide valuable insight into the non-covalent interactions responsible for the stabilization of a given conformer within a structure.
The D–D analysis presented herein provides a rapid, effective and intuitive means of relating experimental and computational DTE geometries for the construction of the crystal landscape. The determination of the crystal landscape for this DTE, and more broadly for all diarylethenes, will provide structural insights that will link the supramolecular interactions found in crystalline solids to the observed conformers, and thus provide a basis for the rational design of next-generation photoactive crystalline materials. landscape analyses based on important geometric parameters and other key properties of interest will serve as an indispensable tool for the broader crystal engineering community.
5. Related literature
The following references are cited in the supporting information: Sheldrick (2008, 2015a,b); Dolomanov et al. (2009); Bruker (2013); Müller et al. (2006).
Supporting information
https://doi.org/10.1107/S2052252523008060/yc5044sup1.cif
contains datablocks dte-1, dte-2, dte-3, dte-4, dte-5, dte-6, dte-7, dte-8, dte-9, dte-10, dte-11, dte-12, dte-13, dte-14, dte-15, dte-16, dte-17, dte-18, dte-19. DOI:Structure factors: contains datablock dte-1. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-1sup2.hkl
Structure factors: contains datablock dte-2. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-2sup3.hkl
Structure factors: contains datablock dte-3. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-3sup4.hkl
Structure factors: contains datablock dte-4. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-4sup5.hkl
Structure factors: contains datablock dte-5. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-5sup6.hkl
Structure factors: contains datablock dte-6. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-6sup7.hkl
Structure factors: contains datablock dte-7. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-7sup8.hkl
Structure factors: contains datablock dte-8. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-8sup9.hkl
Structure factors: contains datablock dte-9. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-9sup10.hkl
Structure factors: contains datablock dte-10. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-10sup11.hkl
Structure factors: contains datablock dte-11. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-11sup12.hkl
Structure factors: contains datablock dte-12. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-12sup13.hkl
Structure factors: contains datablock dte-13. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-13sup14.hkl
Structure factors: contains datablock dte-14. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-14sup15.hkl
Structure factors: contains datablock dte-15. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-15sup16.hkl
Structure factors: contains datablock dte-16. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-16sup17.hkl
Structure factors: contains datablock dte-17. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-17sup18.hkl
Structure factors: contains datablock dte-18. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-18sup19.hkl
Structure factors: contains datablock dte-19. DOI: https://doi.org/10.1107/S2052252523008060/yc5044dte-19sup20.hkl
Supporting data, figures and tables. DOI: https://doi.org/10.1107/S2052252523008060/yc5044sup21.pdf
For all structures, cell
SAINT V8.40B (Bruker AXS, 2016); data reduction: SAINT V8.40B (Bruker AXS, 2016). Program(s) used to solve structure: SHELXT 2018/2 (Sheldrick, 2018) for dte-1, dte-2, dte-3, dte-5, dte-6, dte-8, dte-9, dte-11, dte-12, dte-14, dte-19; SHELXT (Sheldrick, 2015) for dte-4, dte-7, dte-13, dte-15, dte-16, dte-17; SHELXS (Sheldrick, 2008) for dte-10, dte-18. Program(s) used to refine structure: SHELXL 2019/2 (Sheldrick, 2015) for dte-1, dte-2, dte-3, dte-4, dte-5, dte-6, dte-7, dte-9, dte-10, dte-12, dte-13, dte-14, dte-15, dte-16, dte-17, dte-18, dte-19; XL (Sheldrick, 2008) for dte-8; SHELXL 2018/3 (Sheldrick, 2015) for dte-11. For all structures, molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).C34H26N2S2 | Z = 2 |
Mr = 526.69 | F(000) = 552 |
Triclinic, P1 | Dx = 1.314 Mg m−3 |
a = 9.4895 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.6539 (5) Å | Cell parameters from 5978 reflections |
c = 13.4967 (6) Å | θ = 2.5–30.5° |
α = 114.125 (1)° | µ = 0.23 mm−1 |
β = 100.242 (1)° | T = 90 K |
γ = 91.853 (1)° | Prism, colourless |
V = 1331.32 (10) Å3 | 0.06 × 0.04 × 0.04 mm |
Bruker APEX-II CCD diffractometer | 5311 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.044 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0645 before and 0.0476 after correction. The Ratio of minimum to maximum transmission is 0.9487. The λ/2 correction factor is Not present. | θmax = 28.3°, θmin = 1.7° |
Tmin = 0.708, Tmax = 0.746 | h = −12→12 |
27314 measured reflections | k = −15→15 |
6607 independent reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0429P)2 + 0.7802P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
6607 reflections | Δρmax = 0.47 e Å−3 |
347 parameters | Δρmin = −0.31 e Å−3 |
0 restraints |
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 | ||
C28 | 0.91627 (18) | 0.62834 (16) | 0.64367 (14) | 0.0142 (3) | |
S1 | 0.58835 (4) | 1.02666 (4) | 0.87103 (4) | 0.01439 (10) | |
C10 | 0.76546 (18) | 0.99163 (16) | 0.88068 (14) | 0.0128 (3) | |
C11 | 0.52011 (18) | 0.86946 (15) | 0.82114 (14) | 0.0129 (3) | |
C9 | 0.76878 (18) | 0.86485 (15) | 0.84708 (14) | 0.0127 (3) | |
H9 | 0.856036 | 0.827102 | 0.846801 | 0.015* | |
C13 | 0.88700 (18) | 1.09025 (16) | 0.91614 (14) | 0.0143 (3) | |
C8 | 0.62978 (17) | 0.79315 (15) | 0.81222 (13) | 0.0119 (3) | |
C12 | 0.35974 (18) | 0.83449 (17) | 0.79230 (16) | 0.0170 (4) | |
H12A | 0.3266 (5) | 0.8416 (12) | 0.8573 (8) | 0.026* | |
H12B | 0.3365 (4) | 0.7492 (11) | 0.7368 (10) | 0.026* | |
H12C | 0.3138 (6) | 0.8904 (10) | 0.7645 (10) | 0.026* | |
C14 | 1.01583 (19) | 1.06155 (17) | 0.87984 (15) | 0.0180 (4) | |
H14 | 1.027779 | 0.976739 | 0.834367 | 0.022* | |
C17 | 0.87903 (19) | 1.21650 (16) | 0.98366 (15) | 0.0175 (4) | |
H17 | 0.795051 | 1.240847 | 1.012570 | 0.021* | |
C1 | 0.61018 (17) | 0.65304 (15) | 0.77249 (13) | 0.0116 (3) | |
C15 | 1.1264 (2) | 1.15862 (18) | 0.91107 (15) | 0.0214 (4) | |
H15 | 1.213478 | 1.136878 | 0.886270 | 0.026* | |
C16 | 0.9952 (2) | 1.30704 (17) | 1.00858 (16) | 0.0212 (4) | |
H16 | 0.986175 | 1.392893 | 1.053178 | 0.025* | |
C2 | 0.50803 (17) | 0.60160 (15) | 0.82062 (14) | 0.0113 (3) | |
C18 | 0.68780 (17) | 0.58015 (15) | 0.69992 (13) | 0.0111 (3) | |
N1 | 1.11814 (17) | 1.28076 (15) | 0.97380 (13) | 0.0225 (3) | |
C3 | 0.50885 (18) | 0.66158 (16) | 0.93420 (14) | 0.0138 (3) | |
H3 | 0.573694 | 0.735793 | 0.980099 | 0.017* | |
C7 | 0.40814 (18) | 0.49477 (16) | 0.75445 (15) | 0.0144 (3) | |
H7 | 0.404165 | 0.453784 | 0.676846 | 0.017* | |
C19 | 0.70010 (17) | 0.44391 (15) | 0.67251 (14) | 0.0127 (3) | |
C25 | 0.77183 (17) | 0.63527 (15) | 0.64299 (14) | 0.0120 (3) | |
C4 | 0.41591 (19) | 0.61379 (17) | 0.98055 (15) | 0.0164 (3) | |
H4 | 0.418971 | 0.654775 | 1.058031 | 0.020* | |
C6 | 0.31463 (18) | 0.44817 (16) | 0.80146 (15) | 0.0171 (4) | |
H6 | 0.247449 | 0.375567 | 0.755518 | 0.021* | |
C20 | 0.69596 (18) | 0.35851 (16) | 0.56270 (15) | 0.0153 (3) | |
H20 | 0.678680 | 0.387105 | 0.505513 | 0.018* | |
C24 | 0.72781 (18) | 0.39981 (16) | 0.75531 (15) | 0.0159 (3) | |
H24 | 0.731417 | 0.456148 | 0.830440 | 0.019* | |
C26 | 0.70911 (18) | 0.70216 (15) | 0.58098 (14) | 0.0131 (3) | |
H26 | 0.609987 | 0.714434 | 0.571398 | 0.016* | |
C5 | 0.31820 (18) | 0.50631 (17) | 0.91450 (16) | 0.0172 (4) | |
H5 | 0.255078 | 0.473407 | 0.946375 | 0.021* | |
C21 | 0.71666 (19) | 0.23264 (17) | 0.53585 (16) | 0.0197 (4) | |
H21 | 0.712087 | 0.175648 | 0.460751 | 0.024* | |
C23 | 0.75014 (19) | 0.27408 (18) | 0.72857 (17) | 0.0207 (4) | |
H23 | 0.769661 | 0.245328 | 0.785573 | 0.025* | |
C27 | 0.80506 (17) | 0.74678 (16) | 0.53679 (14) | 0.0132 (3) | |
S2 | 0.97545 (4) | 0.70693 (4) | 0.57188 (4) | 0.01602 (10) | |
C29 | 1.02376 (19) | 0.57089 (18) | 0.69953 (16) | 0.0205 (4) | |
H29A | 1.0876 (12) | 0.5358 (12) | 0.6552 (8) | 0.031* | |
H29B | 0.9768 (6) | 0.5094 (12) | 0.7115 (10) | 0.031* | |
H29C | 1.0725 (12) | 0.6323 (8) | 0.7660 (10) | 0.031* | |
C22 | 0.74402 (19) | 0.19042 (17) | 0.61895 (17) | 0.0222 (4) | |
H22 | 0.758534 | 0.104500 | 0.600946 | 0.027* | |
C30 | 0.77912 (18) | 0.81400 (15) | 0.46543 (14) | 0.0137 (3) | |
C31 | 0.64090 (19) | 0.83757 (17) | 0.42852 (15) | 0.0173 (4) | |
H31 | 0.560920 | 0.812916 | 0.451847 | 0.021* | |
C34 | 0.89056 (19) | 0.85427 (17) | 0.42800 (15) | 0.0180 (4) | |
H34 | 0.986959 | 0.840801 | 0.450384 | 0.022* | |
C32 | 0.6210 (2) | 0.89704 (17) | 0.35775 (16) | 0.0199 (4) | |
H32 | 0.525673 | 0.911184 | 0.333258 | 0.024* | |
C33 | 0.8596 (2) | 0.91400 (18) | 0.35802 (15) | 0.0205 (4) | |
H33 | 0.937693 | 0.941181 | 0.334382 | 0.025* | |
N2 | 0.72787 (17) | 0.93605 (14) | 0.32147 (13) | 0.0205 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C28 | 0.0142 (8) | 0.0142 (8) | 0.0147 (8) | 0.0001 (6) | 0.0033 (6) | 0.0066 (7) |
S1 | 0.0136 (2) | 0.00990 (19) | 0.0197 (2) | 0.00043 (15) | 0.00397 (16) | 0.00621 (17) |
C10 | 0.0129 (8) | 0.0148 (8) | 0.0112 (8) | −0.0005 (6) | 0.0027 (6) | 0.0059 (7) |
C11 | 0.0146 (8) | 0.0107 (7) | 0.0138 (8) | −0.0020 (6) | 0.0032 (6) | 0.0056 (6) |
C9 | 0.0123 (8) | 0.0131 (8) | 0.0131 (8) | −0.0003 (6) | 0.0031 (6) | 0.0060 (7) |
C13 | 0.0162 (8) | 0.0147 (8) | 0.0132 (8) | −0.0019 (6) | 0.0014 (6) | 0.0080 (7) |
C8 | 0.0125 (8) | 0.0124 (8) | 0.0105 (8) | −0.0003 (6) | 0.0031 (6) | 0.0043 (6) |
C12 | 0.0121 (8) | 0.0167 (8) | 0.0245 (9) | 0.0014 (6) | 0.0041 (7) | 0.0110 (7) |
C14 | 0.0190 (9) | 0.0177 (8) | 0.0158 (9) | −0.0011 (7) | 0.0046 (7) | 0.0055 (7) |
C17 | 0.0164 (8) | 0.0161 (8) | 0.0192 (9) | −0.0011 (7) | 0.0036 (7) | 0.0070 (7) |
C1 | 0.0113 (7) | 0.0115 (7) | 0.0117 (8) | −0.0007 (6) | 0.0010 (6) | 0.0052 (6) |
C15 | 0.0170 (9) | 0.0270 (10) | 0.0195 (9) | −0.0043 (7) | 0.0057 (7) | 0.0088 (8) |
C16 | 0.0224 (9) | 0.0145 (8) | 0.0235 (10) | −0.0030 (7) | 0.0006 (8) | 0.0069 (8) |
C2 | 0.0101 (7) | 0.0090 (7) | 0.0163 (8) | 0.0023 (6) | 0.0038 (6) | 0.0062 (6) |
C18 | 0.0094 (7) | 0.0127 (7) | 0.0122 (8) | 0.0007 (6) | 0.0014 (6) | 0.0067 (6) |
N1 | 0.0228 (8) | 0.0246 (8) | 0.0202 (8) | −0.0070 (7) | 0.0024 (7) | 0.0109 (7) |
C3 | 0.0119 (8) | 0.0123 (8) | 0.0161 (8) | 0.0007 (6) | 0.0029 (6) | 0.0051 (7) |
C7 | 0.0148 (8) | 0.0117 (8) | 0.0158 (8) | 0.0018 (6) | 0.0044 (7) | 0.0044 (7) |
C19 | 0.0086 (7) | 0.0126 (8) | 0.0169 (8) | 0.0009 (6) | 0.0045 (6) | 0.0055 (7) |
C25 | 0.0127 (8) | 0.0108 (7) | 0.0120 (8) | 0.0001 (6) | 0.0040 (6) | 0.0040 (6) |
C4 | 0.0164 (8) | 0.0194 (9) | 0.0175 (9) | 0.0048 (7) | 0.0073 (7) | 0.0102 (7) |
C6 | 0.0132 (8) | 0.0120 (8) | 0.0253 (10) | −0.0006 (6) | 0.0040 (7) | 0.0072 (7) |
C20 | 0.0139 (8) | 0.0157 (8) | 0.0167 (8) | 0.0009 (6) | 0.0056 (7) | 0.0064 (7) |
C24 | 0.0145 (8) | 0.0171 (8) | 0.0185 (9) | 0.0030 (7) | 0.0051 (7) | 0.0092 (7) |
C26 | 0.0124 (8) | 0.0126 (8) | 0.0142 (8) | 0.0019 (6) | 0.0044 (6) | 0.0049 (7) |
C5 | 0.0148 (8) | 0.0174 (8) | 0.0269 (10) | 0.0031 (7) | 0.0095 (7) | 0.0147 (8) |
C21 | 0.0162 (8) | 0.0140 (8) | 0.0242 (9) | 0.0003 (7) | 0.0094 (7) | 0.0016 (7) |
C23 | 0.0165 (9) | 0.0215 (9) | 0.0307 (10) | 0.0050 (7) | 0.0050 (8) | 0.0173 (8) |
C27 | 0.0117 (8) | 0.0132 (8) | 0.0139 (8) | 0.0003 (6) | 0.0028 (6) | 0.0049 (7) |
S2 | 0.01060 (19) | 0.0217 (2) | 0.0203 (2) | 0.00139 (16) | 0.00575 (16) | 0.01239 (18) |
C29 | 0.0152 (8) | 0.0256 (10) | 0.0238 (10) | 0.0032 (7) | 0.0032 (7) | 0.0138 (8) |
C22 | 0.0167 (9) | 0.0152 (9) | 0.0384 (11) | 0.0063 (7) | 0.0119 (8) | 0.0121 (8) |
C30 | 0.0179 (8) | 0.0106 (7) | 0.0112 (8) | −0.0013 (6) | 0.0042 (6) | 0.0030 (6) |
C31 | 0.0164 (8) | 0.0183 (8) | 0.0217 (9) | 0.0018 (7) | 0.0072 (7) | 0.0117 (7) |
C34 | 0.0151 (8) | 0.0221 (9) | 0.0176 (9) | −0.0022 (7) | 0.0028 (7) | 0.0098 (7) |
C32 | 0.0193 (9) | 0.0191 (9) | 0.0251 (10) | 0.0038 (7) | 0.0055 (7) | 0.0126 (8) |
C33 | 0.0210 (9) | 0.0220 (9) | 0.0194 (9) | −0.0056 (7) | 0.0054 (7) | 0.0098 (8) |
N2 | 0.0256 (8) | 0.0168 (7) | 0.0215 (8) | 0.0007 (6) | 0.0058 (7) | 0.0102 (7) |
C28—C25 | 1.374 (2) | C19—C20 | 1.400 (2) |
C28—S2 | 1.7259 (17) | C19—C24 | 1.399 (2) |
C28—C29 | 1.497 (2) | C25—C26 | 1.431 (2) |
S1—C10 | 1.7374 (17) | C4—H4 | 0.9500 |
S1—C11 | 1.7287 (16) | C4—C5 | 1.393 (2) |
C10—C9 | 1.360 (2) | C6—H6 | 0.9500 |
C10—C13 | 1.466 (2) | C6—C5 | 1.387 (3) |
C11—C8 | 1.380 (2) | C20—H20 | 0.9500 |
C11—C12 | 1.501 (2) | C20—C21 | 1.390 (2) |
C9—H9 | 0.9500 | C24—H24 | 0.9500 |
C9—C8 | 1.430 (2) | C24—C23 | 1.392 (2) |
C13—C14 | 1.397 (2) | C26—H26 | 0.9500 |
C13—C17 | 1.392 (2) | C26—C27 | 1.368 (2) |
C8—C1 | 1.489 (2) | C5—H5 | 0.9500 |
C12—H12A | 0.957 (11) | C21—H21 | 0.9500 |
C12—H12B | 0.957 (11) | C21—C22 | 1.387 (3) |
C12—H12C | 0.957 (11) | C23—H23 | 0.9500 |
C14—H14 | 0.9500 | C23—C22 | 1.389 (3) |
C14—C15 | 1.391 (2) | C27—S2 | 1.7351 (17) |
C17—H17 | 0.9500 | C27—C30 | 1.465 (2) |
C17—C16 | 1.395 (2) | C29—H29A | 0.915 (12) |
C1—C2 | 1.492 (2) | C29—H29B | 0.915 (12) |
C1—C18 | 1.357 (2) | C29—H29C | 0.915 (12) |
C15—H15 | 0.9500 | C22—H22 | 0.9500 |
C15—N1 | 1.340 (3) | C30—C31 | 1.395 (2) |
C16—H16 | 0.9500 | C30—C34 | 1.395 (2) |
C16—N1 | 1.332 (3) | C31—H31 | 0.9500 |
C2—C3 | 1.399 (2) | C31—C32 | 1.383 (2) |
C2—C7 | 1.400 (2) | C34—H34 | 0.9500 |
C18—C19 | 1.489 (2) | C34—C33 | 1.384 (3) |
C18—C25 | 1.492 (2) | C32—H32 | 0.9500 |
C3—H3 | 0.9500 | C32—N2 | 1.343 (2) |
C3—C4 | 1.389 (2) | C33—H33 | 0.9500 |
C7—H7 | 0.9500 | C33—N2 | 1.333 (2) |
C7—C6 | 1.391 (2) | ||
C25—C28—S2 | 110.94 (13) | C28—C25—C18 | 124.64 (15) |
C25—C28—C29 | 130.41 (16) | C28—C25—C26 | 112.35 (15) |
C29—C28—S2 | 118.58 (13) | C26—C25—C18 | 123.00 (14) |
C11—S1—C10 | 92.59 (8) | C3—C4—H4 | 119.7 |
C9—C10—S1 | 110.19 (12) | C3—C4—C5 | 120.63 (16) |
C9—C10—C13 | 128.19 (16) | C5—C4—H4 | 119.7 |
C13—C10—S1 | 121.57 (13) | C7—C6—H6 | 119.6 |
C8—C11—S1 | 111.00 (12) | C5—C6—C7 | 120.87 (16) |
C8—C11—C12 | 129.81 (15) | C5—C6—H6 | 119.6 |
C12—C11—S1 | 119.17 (12) | C19—C20—H20 | 119.4 |
C10—C9—H9 | 122.8 | C21—C20—C19 | 121.18 (17) |
C10—C9—C8 | 114.33 (15) | C21—C20—H20 | 119.4 |
C8—C9—H9 | 122.8 | C19—C24—H24 | 119.7 |
C14—C13—C10 | 120.85 (16) | C23—C24—C19 | 120.56 (17) |
C17—C13—C10 | 122.35 (16) | C23—C24—H24 | 119.7 |
C17—C13—C14 | 116.76 (16) | C25—C26—H26 | 123.1 |
C11—C8—C9 | 111.89 (15) | C27—C26—C25 | 113.80 (15) |
C11—C8—C1 | 125.47 (15) | C27—C26—H26 | 123.1 |
C9—C8—C1 | 122.64 (14) | C4—C5—H5 | 120.6 |
C11—C12—H12A | 109.5 | C6—C5—C4 | 118.89 (16) |
C11—C12—H12B | 109.5 | C6—C5—H5 | 120.6 |
C11—C12—H12C | 109.5 | C20—C21—H21 | 120.1 |
H12A—C12—H12B | 109.5 | C22—C21—C20 | 119.84 (17) |
H12A—C12—H12C | 109.5 | C22—C21—H21 | 120.1 |
H12B—C12—H12C | 109.5 | C24—C23—H23 | 119.8 |
C13—C14—H14 | 120.4 | C22—C23—C24 | 120.33 (17) |
C15—C14—C13 | 119.20 (17) | C22—C23—H23 | 119.8 |
C15—C14—H14 | 120.4 | C26—C27—S2 | 110.10 (13) |
C13—C17—H17 | 120.2 | C26—C27—C30 | 129.11 (15) |
C13—C17—C16 | 119.51 (17) | C30—C27—S2 | 120.74 (12) |
C16—C17—H17 | 120.2 | C28—S2—C27 | 92.79 (8) |
C8—C1—C2 | 116.38 (14) | C28—C29—H29A | 109.5 |
C18—C1—C8 | 119.90 (14) | C28—C29—H29B | 109.5 |
C18—C1—C2 | 123.66 (15) | C28—C29—H29C | 109.5 |
C14—C15—H15 | 117.8 | H29A—C29—H29B | 109.5 |
N1—C15—C14 | 124.36 (18) | H29A—C29—H29C | 109.5 |
N1—C15—H15 | 117.8 | H29B—C29—H29C | 109.5 |
C17—C16—H16 | 117.9 | C21—C22—C23 | 119.83 (16) |
N1—C16—C17 | 124.15 (17) | C21—C22—H22 | 120.1 |
N1—C16—H16 | 117.9 | C23—C22—H22 | 120.1 |
C3—C2—C1 | 120.03 (14) | C31—C30—C27 | 121.71 (15) |
C3—C2—C7 | 118.35 (15) | C34—C30—C27 | 121.78 (16) |
C7—C2—C1 | 121.62 (15) | C34—C30—C31 | 116.48 (16) |
C1—C18—C19 | 124.45 (15) | C30—C31—H31 | 120.2 |
C1—C18—C25 | 120.60 (14) | C32—C31—C30 | 119.62 (16) |
C19—C18—C25 | 114.93 (14) | C32—C31—H31 | 120.2 |
C16—N1—C15 | 115.98 (16) | C30—C34—H34 | 120.3 |
C2—C3—H3 | 119.6 | C33—C34—C30 | 119.49 (17) |
C4—C3—C2 | 120.72 (16) | C33—C34—H34 | 120.3 |
C4—C3—H3 | 119.6 | C31—C32—H32 | 117.9 |
C2—C7—H7 | 119.7 | N2—C32—C31 | 124.16 (17) |
C6—C7—C2 | 120.51 (16) | N2—C32—H32 | 117.9 |
C6—C7—H7 | 119.7 | C34—C33—H33 | 117.7 |
C20—C19—C18 | 119.98 (15) | N2—C33—C34 | 124.55 (17) |
C24—C19—C18 | 121.56 (15) | N2—C33—H33 | 117.7 |
C24—C19—C20 | 118.25 (15) | C33—N2—C32 | 115.70 (16) |
C28—C25—C26—C27 | −0.9 (2) | C2—C7—C6—C5 | 0.0 (3) |
S1—C10—C9—C8 | 0.43 (19) | C18—C1—C2—C3 | 134.97 (17) |
S1—C10—C13—C14 | −151.77 (14) | C18—C1—C2—C7 | −46.1 (2) |
S1—C10—C13—C17 | 26.0 (2) | C18—C19—C20—C21 | 175.72 (15) |
S1—C11—C8—C9 | 0.32 (18) | C18—C19—C24—C23 | −174.91 (16) |
S1—C11—C8—C1 | 179.80 (13) | C18—C25—C26—C27 | 179.04 (15) |
C10—S1—C11—C8 | −0.07 (13) | C3—C2—C7—C6 | −1.5 (2) |
C10—S1—C11—C12 | −178.80 (14) | C3—C4—C5—C6 | −0.4 (3) |
C10—C9—C8—C11 | −0.5 (2) | C7—C2—C3—C4 | 2.0 (2) |
C10—C9—C8—C1 | −179.99 (15) | C7—C6—C5—C4 | 0.9 (3) |
C10—C13—C14—C15 | 177.04 (16) | C19—C18—C25—C28 | −52.5 (2) |
C10—C13—C17—C16 | −175.87 (16) | C19—C18—C25—C26 | 127.57 (16) |
C11—S1—C10—C9 | −0.21 (13) | C19—C20—C21—C22 | −0.9 (3) |
C11—S1—C10—C13 | 177.33 (14) | C19—C24—C23—C22 | −0.5 (3) |
C11—C8—C1—C2 | −46.9 (2) | C25—C28—S2—C27 | −1.46 (14) |
C11—C8—C1—C18 | 135.76 (18) | C25—C18—C19—C20 | −42.2 (2) |
C9—C10—C13—C14 | 25.3 (3) | C25—C18—C19—C24 | 132.44 (16) |
C9—C10—C13—C17 | −156.96 (18) | C25—C26—C27—S2 | −0.21 (19) |
C9—C8—C1—C2 | 132.54 (16) | C25—C26—C27—C30 | 177.14 (16) |
C9—C8—C1—C18 | −44.8 (2) | C20—C19—C24—C23 | −0.2 (2) |
C13—C10—C9—C8 | −176.89 (16) | C20—C21—C22—C23 | 0.2 (3) |
C13—C14—C15—N1 | −0.8 (3) | C24—C19—C20—C21 | 0.9 (2) |
C13—C17—C16—N1 | −1.7 (3) | C24—C23—C22—C21 | 0.5 (3) |
C8—C1—C2—C3 | −42.3 (2) | C26—C27—S2—C28 | 0.94 (14) |
C8—C1—C2—C7 | 136.62 (16) | C26—C27—C30—C31 | −2.6 (3) |
C8—C1—C18—C19 | 166.91 (15) | C26—C27—C30—C34 | 179.45 (17) |
C8—C1—C18—C25 | −11.5 (2) | C27—C30—C31—C32 | −177.49 (16) |
C12—C11—C8—C9 | 178.87 (17) | C27—C30—C34—C33 | 178.05 (16) |
C12—C11—C8—C1 | −1.7 (3) | S2—C28—C25—C18 | −178.36 (13) |
C14—C13—C17—C16 | 2.0 (3) | S2—C28—C25—C26 | 1.58 (19) |
C14—C15—N1—C16 | 1.2 (3) | S2—C27—C30—C31 | 174.50 (14) |
C17—C13—C14—C15 | −0.8 (3) | S2—C27—C30—C34 | −3.4 (2) |
C17—C16—N1—C15 | 0.1 (3) | C29—C28—C25—C18 | −1.6 (3) |
C1—C2—C3—C4 | −179.05 (15) | C29—C28—C25—C26 | 178.36 (17) |
C1—C2—C7—C6 | 179.59 (15) | C29—C28—S2—C27 | −178.67 (14) |
C1—C18—C19—C20 | 139.29 (17) | C30—C27—S2—C28 | −176.67 (14) |
C1—C18—C19—C24 | −46.1 (2) | C30—C31—C32—N2 | −0.6 (3) |
C1—C18—C25—C28 | 126.09 (18) | C30—C34—C33—N2 | −0.6 (3) |
C1—C18—C25—C26 | −53.8 (2) | C31—C30—C34—C33 | 0.0 (3) |
C2—C1—C18—C19 | −10.2 (3) | C31—C32—N2—C33 | 0.1 (3) |
C2—C1—C18—C25 | 171.31 (15) | C34—C30—C31—C32 | 0.6 (3) |
C2—C3—C4—C5 | −1.1 (3) | C34—C33—N2—C32 | 0.6 (3) |
C34H26N2S2 | F(000) = 1104 |
Mr = 526.69 | Dx = 1.321 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8916 (4) Å | Cell parameters from 9978 reflections |
b = 25.9653 (10) Å | θ = 2.3–33.2° |
c = 10.9370 (6) Å | µ = 0.23 mm−1 |
β = 109.525 (1)° | T = 90 K |
V = 2647.5 (2) Å3 | Prism, colourless |
Z = 4 | 0.2 × 0.04 × 0.02 mm |
Bruker APEX-II CCD diffractometer | 4646 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.020 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1226 before and 0.0326 after correction. The Ratio of minimum to maximum transmission is 0.9578. The λ/2 correction factor is Not present. | θmax = 33.2°, θmin = 1.6° |
Tmin = 0.715, Tmax = 0.747 | h = −15→15 |
28558 measured reflections | k = −39→39 |
5068 independent reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0492P)2 + 1.8517P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
5068 reflections | Δρmax = 0.56 e Å−3 |
220 parameters | Δρmin = −0.26 e Å−3 |
0 restraints |
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) | |
S1 | 0.56790 (2) | 0.38312 (2) | 0.48033 (2) | 0.01569 (6) | |
C1 | 0.31529 (8) | 0.26358 (3) | 0.49148 (7) | 0.01159 (12) | |
C2 | 0.39805 (8) | 0.21556 (3) | 0.49264 (7) | 0.01218 (12) | |
C3 | 0.45934 (9) | 0.20691 (3) | 0.39582 (8) | 0.01690 (14) | |
H3 | 0.442833 | 0.230763 | 0.326493 | 0.020* | |
C4 | 0.54421 (10) | 0.16363 (3) | 0.40048 (9) | 0.02052 (16) | |
H4 | 0.583998 | 0.157955 | 0.333684 | 0.025* | |
C5 | 0.57112 (9) | 0.12866 (3) | 0.50233 (9) | 0.01877 (15) | |
H5 | 0.629476 | 0.099277 | 0.505637 | 0.023* | |
C6 | 0.51151 (9) | 0.13721 (3) | 0.59939 (8) | 0.01670 (14) | |
H6 | 0.530001 | 0.113653 | 0.669537 | 0.020* | |
C7 | 0.42503 (8) | 0.18005 (3) | 0.59432 (8) | 0.01462 (13) | |
H7 | 0.383984 | 0.185210 | 0.660461 | 0.018* | |
C8 | 0.38456 (8) | 0.31192 (3) | 0.47037 (7) | 0.01121 (12) | |
C9 | 0.30954 (8) | 0.35201 (3) | 0.38488 (7) | 0.01415 (13) | |
H9 | 0.210203 | 0.350201 | 0.335993 | 0.017* | |
C10 | 0.39382 (9) | 0.39325 (3) | 0.37984 (8) | 0.01513 (14) | |
C11 | 0.52860 (8) | 0.32343 (3) | 0.52868 (7) | 0.01290 (13) | |
C12 | 0.64632 (8) | 0.29268 (3) | 0.62276 (8) | 0.01749 (15) | |
H12A | 0.6833 (7) | 0.2676 (3) | 0.5753 (4) | 0.026* | |
H12B | 0.6087 (4) | 0.2747 (3) | 0.6830 (7) | 0.026* | |
H12C | 0.7237 (7) | 0.31577 (19) | 0.6712 (7) | 0.026* | |
C13 | 0.35327 (11) | 0.44062 (4) | 0.30369 (11) | 0.0257 (2) | |
N1 | 0.2850 (2) | 0.54103 (8) | 0.1908 (2) | 0.0297 (4) | 0.507 (2) |
C14 | 0.2186 (2) | 0.45673 (8) | 0.2446 (2) | 0.0323 (5) | 0.507 (2) |
H14 | 0.141655 | 0.434457 | 0.242543 | 0.039* | 0.507 (2) |
C15 | 0.1869 (3) | 0.50499 (9) | 0.1858 (3) | 0.0375 (6) | 0.507 (2) |
H15 | 0.089284 | 0.512717 | 0.139209 | 0.045* | 0.507 (2) |
C16 | 0.4215 (3) | 0.52858 (9) | 0.2569 (2) | 0.0228 (4) | 0.507 (2) |
H16 | 0.493577 | 0.553468 | 0.261951 | 0.027* | 0.507 (2) |
C17 | 0.4642 (2) | 0.48164 (7) | 0.3185 (2) | 0.0194 (3) | 0.507 (2) |
H17 | 0.561675 | 0.475655 | 0.368978 | 0.023* | 0.507 (2) |
N1A | 0.2564 (3) | 0.52289 (8) | 0.1277 (2) | 0.0319 (5) | 0.493 (2) |
C14A | 0.24258 (19) | 0.43237 (7) | 0.16842 (19) | 0.0212 (4) | 0.493 (2) |
H14A | 0.203562 | 0.399367 | 0.139266 | 0.025* | 0.493 (2) |
C15A | 0.2026 (2) | 0.47596 (8) | 0.0909 (2) | 0.0285 (5) | 0.493 (2) |
H15A | 0.133109 | 0.472191 | 0.007000 | 0.034* | 0.493 (2) |
C16A | 0.3538 (5) | 0.52685 (9) | 0.2451 (3) | 0.0321 (6) | 0.493 (2) |
H16A | 0.392682 | 0.559955 | 0.273238 | 0.039* | 0.493 (2) |
C17A | 0.4030 (3) | 0.48525 (8) | 0.3306 (2) | 0.0270 (5) | 0.493 (2) |
H17A | 0.476281 | 0.491099 | 0.411493 | 0.032* | 0.493 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01390 (9) | 0.01385 (9) | 0.01924 (10) | −0.00307 (6) | 0.00541 (7) | 0.00046 (6) |
C1 | 0.0107 (3) | 0.0115 (3) | 0.0130 (3) | 0.0004 (2) | 0.0046 (2) | 0.0005 (2) |
C2 | 0.0109 (3) | 0.0116 (3) | 0.0147 (3) | 0.0005 (2) | 0.0051 (2) | 0.0007 (2) |
C3 | 0.0201 (3) | 0.0143 (3) | 0.0205 (3) | 0.0033 (3) | 0.0123 (3) | 0.0028 (3) |
C4 | 0.0242 (4) | 0.0161 (3) | 0.0279 (4) | 0.0052 (3) | 0.0176 (3) | 0.0030 (3) |
C5 | 0.0167 (3) | 0.0132 (3) | 0.0289 (4) | 0.0033 (3) | 0.0110 (3) | 0.0028 (3) |
C6 | 0.0156 (3) | 0.0142 (3) | 0.0201 (3) | 0.0018 (3) | 0.0057 (3) | 0.0041 (3) |
C7 | 0.0145 (3) | 0.0146 (3) | 0.0153 (3) | 0.0011 (2) | 0.0057 (2) | 0.0020 (2) |
C8 | 0.0099 (3) | 0.0115 (3) | 0.0128 (3) | 0.0008 (2) | 0.0046 (2) | 0.0006 (2) |
C9 | 0.0116 (3) | 0.0160 (3) | 0.0154 (3) | 0.0020 (2) | 0.0053 (2) | 0.0037 (2) |
C10 | 0.0151 (3) | 0.0142 (3) | 0.0179 (3) | 0.0025 (2) | 0.0079 (3) | 0.0036 (2) |
C11 | 0.0108 (3) | 0.0134 (3) | 0.0145 (3) | 0.0000 (2) | 0.0043 (2) | 0.0006 (2) |
C12 | 0.0119 (3) | 0.0204 (4) | 0.0181 (3) | 0.0018 (3) | 0.0023 (3) | 0.0036 (3) |
C13 | 0.0259 (4) | 0.0232 (4) | 0.0351 (5) | 0.0101 (3) | 0.0193 (4) | 0.0165 (4) |
N1 | 0.0396 (10) | 0.0185 (8) | 0.0276 (9) | 0.0013 (7) | 0.0066 (8) | 0.0082 (8) |
C14 | 0.0235 (9) | 0.0214 (9) | 0.0424 (12) | −0.0015 (7) | −0.0020 (8) | 0.0151 (8) |
C15 | 0.0327 (11) | 0.0230 (9) | 0.0457 (13) | 0.0026 (8) | −0.0016 (9) | 0.0158 (9) |
C16 | 0.0322 (11) | 0.0138 (8) | 0.0254 (9) | −0.0007 (8) | 0.0135 (9) | 0.0028 (6) |
C17 | 0.0219 (8) | 0.0132 (7) | 0.0266 (9) | −0.0008 (6) | 0.0129 (7) | 0.0022 (6) |
N1A | 0.0515 (12) | 0.0163 (8) | 0.0315 (10) | 0.0090 (8) | 0.0184 (9) | 0.0085 (8) |
C14A | 0.0177 (7) | 0.0172 (7) | 0.0269 (8) | 0.0021 (6) | 0.0049 (6) | 0.0086 (6) |
C15A | 0.0275 (9) | 0.0244 (9) | 0.0320 (10) | 0.0073 (7) | 0.0079 (8) | 0.0148 (8) |
C16A | 0.0580 (19) | 0.0116 (8) | 0.0284 (12) | −0.0019 (12) | 0.0167 (15) | 0.0014 (8) |
C17A | 0.0462 (15) | 0.0148 (8) | 0.0198 (8) | −0.0059 (9) | 0.0110 (9) | −0.0001 (6) |
S1—C10 | 1.7255 (8) | C12—H12B | 0.977 (8) |
S1—C11 | 1.7235 (8) | C12—H12C | 0.977 (8) |
C1—C1i | 1.3653 (14) | C13—C14 | 1.339 (2) |
C1—C2 | 1.4892 (10) | C13—C17 | 1.499 (2) |
C1—C8 | 1.4846 (10) | C13—C14A | 1.533 (2) |
C2—C3 | 1.4030 (11) | C13—C17A | 1.255 (2) |
C2—C7 | 1.3999 (11) | N1—C15 | 1.336 (3) |
C3—H3 | 0.9500 | N1—C16 | 1.341 (3) |
C3—C4 | 1.3933 (11) | C14—H14 | 0.9500 |
C4—H4 | 0.9500 | C14—C15 | 1.396 (3) |
C4—C5 | 1.3923 (12) | C15—H15 | 0.9500 |
C5—H5 | 0.9500 | C16—H16 | 0.9500 |
C5—C6 | 1.3936 (12) | C16—C17 | 1.388 (3) |
C6—H6 | 0.9500 | C17—H17 | 0.9500 |
C6—C7 | 1.3929 (11) | N1A—C15A | 1.337 (3) |
C7—H7 | 0.9500 | N1A—C16A | 1.327 (4) |
C8—C9 | 1.4300 (10) | C14A—H14A | 0.9500 |
C8—C11 | 1.3852 (10) | C14A—C15A | 1.390 (3) |
C9—H9 | 0.9500 | C15A—H15A | 0.9500 |
C9—C10 | 1.3694 (11) | C16A—H16A | 0.9500 |
C10—C13 | 1.4642 (12) | C16A—C17A | 1.405 (3) |
C11—C12 | 1.5004 (11) | C17A—H17A | 0.9500 |
C12—H12A | 0.977 (8) | ||
C11—S1—C10 | 93.05 (4) | C11—C12—H12C | 109.5 |
C1i—C1—C2 | 122.77 (4) | H12A—C12—H12B | 109.5 |
C1i—C1—C8 | 121.88 (4) | H12A—C12—H12C | 109.5 |
C8—C1—C2 | 115.35 (6) | H12B—C12—H12C | 109.5 |
C3—C2—C1 | 120.17 (7) | C10—C13—C17 | 118.95 (11) |
C7—C2—C1 | 121.10 (7) | C10—C13—C14A | 113.76 (11) |
C7—C2—C3 | 118.58 (7) | C14—C13—C10 | 125.19 (12) |
C2—C3—H3 | 119.7 | C14—C13—C17 | 113.87 (13) |
C4—C3—C2 | 120.57 (8) | C17A—C13—C10 | 129.11 (14) |
C4—C3—H3 | 119.7 | C17A—C13—C14A | 116.94 (14) |
C3—C4—H4 | 119.8 | C15—N1—C16 | 116.13 (19) |
C5—C4—C3 | 120.47 (8) | C13—C14—H14 | 118.8 |
C5—C4—H4 | 119.8 | C13—C14—C15 | 122.50 (19) |
C4—C5—H5 | 120.4 | C15—C14—H14 | 118.8 |
C4—C5—C6 | 119.28 (7) | N1—C15—C14 | 124.2 (2) |
C6—C5—H5 | 120.4 | N1—C15—H15 | 117.9 |
C5—C6—H6 | 119.8 | C14—C15—H15 | 117.9 |
C7—C6—C5 | 120.50 (7) | N1—C16—H16 | 117.9 |
C7—C6—H6 | 119.8 | N1—C16—C17 | 124.1 (2) |
C2—C7—H7 | 119.7 | C17—C16—H16 | 117.9 |
C6—C7—C2 | 120.60 (7) | C13—C17—H17 | 120.7 |
C6—C7—H7 | 119.7 | C16—C17—C13 | 118.58 (19) |
C9—C8—C1 | 123.48 (7) | C16—C17—H17 | 120.7 |
C11—C8—C1 | 124.61 (7) | C16A—N1A—C15A | 116.70 (19) |
C11—C8—C9 | 111.90 (7) | C13—C14A—H14A | 121.9 |
C8—C9—H9 | 123.0 | C15A—C14A—C13 | 116.14 (17) |
C10—C9—C8 | 113.94 (7) | C15A—C14A—H14A | 121.9 |
C10—C9—H9 | 123.0 | N1A—C15A—C14A | 123.7 (2) |
C9—C10—S1 | 110.27 (6) | N1A—C15A—H15A | 118.1 |
C9—C10—C13 | 128.68 (8) | C14A—C15A—H15A | 118.1 |
C13—C10—S1 | 121.05 (7) | N1A—C16A—H16A | 117.9 |
C8—C11—S1 | 110.83 (6) | N1A—C16A—C17A | 124.2 (2) |
C8—C11—C12 | 130.09 (7) | C17A—C16A—H16A | 117.9 |
C12—C11—S1 | 119.08 (6) | C13—C17A—C16A | 122.2 (2) |
C11—C12—H12A | 109.5 | C13—C17A—H17A | 118.9 |
C11—C12—H12B | 109.5 | C16A—C17A—H17A | 118.9 |
S1—C10—C13—C14 | −165.64 (16) | C9—C8—C11—C12 | −179.24 (8) |
S1—C10—C13—C17 | −2.70 (15) | C9—C10—C13—C14 | 14.6 (2) |
S1—C10—C13—C14A | 142.77 (10) | C9—C10—C13—C17 | 177.51 (12) |
S1—C10—C13—C17A | −32.1 (2) | C9—C10—C13—C14A | −37.03 (14) |
C1i—C1—C2—C3 | 133.26 (10) | C9—C10—C13—C17A | 148.1 (2) |
C1i—C1—C2—C7 | −51.31 (13) | C10—S1—C11—C8 | −0.87 (6) |
C1i—C1—C8—C9 | −43.96 (13) | C10—S1—C11—C12 | 179.47 (7) |
C1i—C1—C8—C11 | 137.07 (10) | C10—C13—C14—C15 | 172.5 (2) |
C1—C2—C3—C4 | 176.08 (8) | C10—C13—C17—C16 | −173.13 (16) |
C1—C2—C7—C6 | −175.18 (7) | C10—C13—C14A—C15A | −178.65 (15) |
C1—C8—C9—C10 | 179.98 (7) | C10—C13—C17A—C16A | 178.8 (2) |
C1—C8—C11—S1 | −179.77 (6) | C11—S1—C10—C9 | 0.34 (6) |
C1—C8—C11—C12 | −0.16 (13) | C11—S1—C10—C13 | −179.49 (8) |
C2—C1—C8—C9 | 136.03 (7) | C11—C8—C9—C10 | −0.93 (10) |
C2—C1—C8—C11 | −42.95 (10) | C13—C14—C15—N1 | −5.3 (5) |
C2—C3—C4—C5 | −0.89 (14) | C13—C14A—C15A—N1A | 0.9 (3) |
C3—C2—C7—C6 | 0.32 (12) | N1—C16—C17—C13 | 4.3 (3) |
C3—C4—C5—C6 | 0.38 (14) | C14—C13—C17—C16 | −8.3 (3) |
C4—C5—C6—C7 | 0.48 (13) | C15—N1—C16—C17 | −0.1 (4) |
C5—C6—C7—C2 | −0.83 (12) | C16—N1—C15—C14 | 0.3 (4) |
C7—C2—C3—C4 | 0.53 (12) | C17—C13—C14—C15 | 8.8 (3) |
C8—C1—C2—C3 | −46.73 (10) | N1A—C16A—C17A—C13 | −2.9 (5) |
C8—C1—C2—C7 | 128.71 (8) | C14A—C13—C17A—C16A | 4.1 (4) |
C8—C9—C10—S1 | 0.26 (9) | C15A—N1A—C16A—C17A | 0.5 (5) |
C8—C9—C10—C13 | −179.92 (8) | C16A—N1A—C15A—C14A | 0.3 (4) |
C9—C8—C11—S1 | 1.15 (8) | C17A—C13—C14A—C15A | −3.1 (3) |
Symmetry code: (i) −x+1/2, y, −z+1. |
C34H27N2S2·C34H28N2S2·C8H5O6·C8H4O6 | F(000) = 1512 |
Mr = 1449.63 | Dx = 1.359 Mg m−3 |
Monoclinic, P2/n | Mo Kα radiation, λ = 0.71073 Å |
a = 17.1862 (6) Å | Cell parameters from 9947 reflections |
b = 12.2494 (4) Å | θ = 2.4–27.2° |
c = 18.3174 (6) Å | µ = 0.20 mm−1 |
β = 113.273 (1)° | T = 90 K |
V = 3542.4 (2) Å3 | Prism, yellow |
Z = 2 | 0.2 × 0.1 × 0.04 mm |
Bruker APEX-II CCD diffractometer | 8497 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.059 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1284 before and 0.0553 after correction. The Ratio of minimum to maximum transmission is 0.9360. The λ/2 correction factor is Not present. | θmax = 30.5°, θmin = 1.7° |
Tmin = 0.699, Tmax = 0.747 | h = −24→24 |
80900 measured reflections | k = −17→17 |
10820 independent reflections | l = −26→26 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.057P)2 + 1.9404P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
10820 reflections | Δρmax = 0.48 e Å−3 |
496 parameters | Δρmin = −0.49 e Å−3 |
7 restraints |
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) | |
S1 | 0.67787 (2) | 0.70513 (3) | 0.37828 (2) | 0.02098 (9) | |
N1 | 0.90453 (9) | 1.02391 (10) | 0.42293 (8) | 0.0241 (3) | |
C1 | 0.73864 (9) | 0.44109 (10) | 0.28170 (8) | 0.0145 (2) | |
C2 | 0.71834 (9) | 0.34031 (11) | 0.31612 (8) | 0.0155 (2) | |
C3 | 0.74868 (10) | 0.32700 (12) | 0.39854 (9) | 0.0188 (3) | |
H3 | 0.784404 | 0.381168 | 0.432516 | 0.023* | |
C4 | 0.72712 (11) | 0.23531 (13) | 0.43132 (10) | 0.0239 (3) | |
H4 | 0.748786 | 0.226681 | 0.487394 | 0.029* | |
C5 | 0.67392 (11) | 0.15627 (13) | 0.38218 (10) | 0.0260 (3) | |
H5 | 0.658767 | 0.093889 | 0.404474 | 0.031* | |
C6 | 0.64311 (11) | 0.16916 (13) | 0.30032 (10) | 0.0245 (3) | |
H6 | 0.606777 | 0.115279 | 0.266594 | 0.029* | |
C7 | 0.66497 (9) | 0.26023 (11) | 0.26728 (9) | 0.0186 (3) | |
H7 | 0.643528 | 0.268125 | 0.211158 | 0.022* | |
C8 | 0.73203 (9) | 0.54543 (11) | 0.32062 (8) | 0.0156 (3) | |
C9 | 0.79362 (9) | 0.63032 (11) | 0.33762 (8) | 0.0172 (3) | |
H9 | 0.844096 | 0.623436 | 0.328468 | 0.021* | |
C10 | 0.77315 (9) | 0.72252 (11) | 0.36831 (8) | 0.0176 (3) | |
C11 | 0.66523 (9) | 0.57463 (11) | 0.34059 (9) | 0.0177 (3) | |
C12 | 0.58623 (10) | 0.51355 (13) | 0.33076 (10) | 0.0235 (3) | |
H12A | 0.5528 (6) | 0.5564 (7) | 0.3492 (7) | 0.035* | |
H12B | 0.6006 (2) | 0.4487 (10) | 0.3598 (7) | 0.035* | |
H12C | 0.5559 (6) | 0.4975 (9) | 0.2771 (7) | 0.035* | |
C13 | 0.81913 (9) | 0.82566 (11) | 0.38826 (8) | 0.0187 (3) | |
C14 | 0.87476 (11) | 0.85512 (12) | 0.35292 (10) | 0.0237 (3) | |
H14 | 0.883806 | 0.807503 | 0.316082 | 0.028* | |
C15 | 0.91652 (11) | 0.95413 (13) | 0.37201 (10) | 0.0256 (3) | |
H15 | 0.954843 | 0.973272 | 0.348343 | 0.031* | |
C16 | 0.85206 (11) | 0.99723 (12) | 0.45773 (10) | 0.0255 (3) | |
H16 | 0.844317 | 1.046927 | 0.494110 | 0.031* | |
C17 | 0.80875 (11) | 0.89942 (12) | 0.44229 (10) | 0.0243 (3) | |
H17 | 0.772067 | 0.882101 | 0.468138 | 0.029* | |
S2 | 0.90675 (2) | 0.25485 (3) | 0.72623 (2) | 0.01972 (8) | |
N2 | 0.68816 (10) | 0.56469 (11) | 0.56368 (9) | 0.0277 (3) | |
C18 | 0.78207 (9) | −0.01740 (11) | 0.73700 (8) | 0.0154 (3) | |
C19 | 0.82835 (9) | −0.11542 (11) | 0.72752 (8) | 0.0166 (3) | |
C20 | 0.85540 (9) | −0.12003 (12) | 0.66490 (9) | 0.0195 (3) | |
H20 | 0.838388 | −0.064584 | 0.625435 | 0.023* | |
C21 | 0.90683 (10) | −0.20462 (13) | 0.65963 (10) | 0.0252 (3) | |
H21 | 0.924458 | −0.207143 | 0.616605 | 0.030* | |
C22 | 0.93232 (12) | −0.28536 (15) | 0.71744 (11) | 0.0319 (4) | |
H22 | 0.968446 | −0.342461 | 0.714631 | 0.038* | |
C23 | 0.90498 (12) | −0.28279 (14) | 0.77965 (11) | 0.0298 (4) | |
H23 | 0.921907 | −0.338613 | 0.818841 | 0.036* | |
C24 | 0.85300 (10) | −0.19864 (12) | 0.78436 (9) | 0.0208 (3) | |
H24 | 0.834037 | −0.197629 | 0.826549 | 0.025* | |
C25 | 0.81330 (9) | 0.08867 (11) | 0.71911 (8) | 0.0158 (3) | |
C26 | 0.75868 (9) | 0.17084 (11) | 0.67094 (9) | 0.0176 (3) | |
H26 | 0.699529 | 0.160383 | 0.642542 | 0.021* | |
C27 | 0.79922 (9) | 0.26670 (11) | 0.66922 (9) | 0.0186 (3) | |
C28 | 0.89669 (9) | 0.12228 (11) | 0.75182 (9) | 0.0175 (3) | |
C29 | 0.97392 (9) | 0.06113 (13) | 0.80525 (9) | 0.0216 (3) | |
H29A | 0.9912 (5) | 0.0126 (9) | 0.7748 (4) | 0.032* | |
H29B | 0.9611 (3) | 0.0216 (9) | 0.8431 (6) | 0.032* | |
H29C | 1.0178 (6) | 0.1109 (6) | 0.8314 (6) | 0.032* | |
C30 | 0.76112 (10) | 0.36883 (12) | 0.63095 (9) | 0.0210 (3) | |
C31 | 0.67364 (11) | 0.38151 (13) | 0.59615 (11) | 0.0304 (4) | |
H31 | 0.637739 | 0.321993 | 0.595000 | 0.036* | |
C32 | 0.63896 (11) | 0.48038 (14) | 0.56330 (11) | 0.0314 (4) | |
H32 | 0.579132 | 0.488539 | 0.540056 | 0.038* | |
C33 | 0.77136 (13) | 0.55438 (15) | 0.59400 (14) | 0.0407 (5) | |
H33 | 0.805238 | 0.614801 | 0.592255 | 0.049* | |
H1 | 0.929 (3) | 1.089 (2) | 0.430 (3) | 0.049* | 0.5 |
H2 | 0.6659 (15) | 0.6339 (15) | 0.5463 (14) | 0.049* | |
H1A | 0.556 (3) | 0.152 (2) | 0.067 (3) | 0.049* | 0.5 |
H3B | 0.475 (2) | 0.6625 (18) | 0.118 (2) | 0.049* | 0.71 (3) |
H4A | 0.677 (4) | 0.815 (4) | 0.548 (4) | 0.049* | 0.36 (4) |
H6A | 0.322 (2) | 1.1022 (16) | 0.467 (2) | 0.049* | 0.64 (4) |
C34 | 0.81024 (12) | 0.45822 (14) | 0.62809 (13) | 0.0369 (4) | |
H34 | 0.870254 | 0.452693 | 0.649574 | 0.044* | |
O1 | 0.54130 (8) | 0.21739 (9) | 0.06672 (7) | 0.0239 (2) | |
O2 | 0.55774 (8) | 0.22877 (9) | −0.04826 (7) | 0.0244 (2) | |
O3 | 0.49579 (8) | 0.59962 (10) | 0.13366 (6) | 0.0234 (2) | |
C35 | 0.54114 (9) | 0.27013 (12) | 0.00620 (9) | 0.0194 (3) | |
C36 | 0.51986 (9) | 0.38895 (11) | 0.00321 (8) | 0.0165 (3) | |
C37 | 0.51644 (9) | 0.44123 (12) | 0.06941 (9) | 0.0184 (3) | |
H37 | 0.527731 | 0.401019 | 0.116858 | 0.022* | |
C38 | 0.49672 (9) | 0.55139 (12) | 0.06681 (8) | 0.0177 (3) | |
O4 | 0.64074 (8) | 0.76402 (10) | 0.53206 (7) | 0.0262 (2) | |
O5 | 0.51063 (9) | 0.69926 (10) | 0.50081 (9) | 0.0370 (3) | |
O6 | 0.33176 (7) | 1.03259 (10) | 0.47268 (7) | 0.0268 (2) | |
C39 | 0.56047 (11) | 0.77565 (13) | 0.51341 (9) | 0.0233 (3) | |
C40 | 0.53082 (9) | 0.89270 (12) | 0.50820 (8) | 0.0188 (3) | |
C41 | 0.44681 (9) | 0.91266 (12) | 0.49473 (9) | 0.0195 (3) | |
H41 | 0.410281 | 0.852963 | 0.491429 | 0.023* | |
C42 | 0.41500 (9) | 1.01872 (12) | 0.48595 (9) | 0.0192 (3) | |
H3A | 0.450 (2) | 0.574 (5) | 0.130 (4) | 0.023* | 0.29 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02689 (19) | 0.01468 (16) | 0.02356 (18) | 0.00325 (13) | 0.01230 (15) | −0.00227 (13) |
N1 | 0.0319 (7) | 0.0120 (5) | 0.0228 (6) | −0.0010 (5) | 0.0047 (5) | −0.0023 (5) |
C1 | 0.0176 (6) | 0.0092 (5) | 0.0153 (6) | 0.0004 (5) | 0.0051 (5) | 0.0000 (4) |
C2 | 0.0188 (6) | 0.0106 (6) | 0.0181 (6) | 0.0012 (5) | 0.0083 (5) | 0.0012 (5) |
C3 | 0.0245 (7) | 0.0144 (6) | 0.0177 (6) | 0.0021 (5) | 0.0087 (6) | 0.0009 (5) |
C4 | 0.0338 (8) | 0.0198 (7) | 0.0206 (7) | 0.0046 (6) | 0.0135 (6) | 0.0062 (6) |
C5 | 0.0349 (9) | 0.0168 (7) | 0.0323 (8) | −0.0007 (6) | 0.0198 (7) | 0.0067 (6) |
C6 | 0.0288 (8) | 0.0156 (7) | 0.0303 (8) | −0.0059 (6) | 0.0129 (7) | −0.0002 (6) |
C7 | 0.0223 (7) | 0.0143 (6) | 0.0187 (6) | −0.0013 (5) | 0.0075 (5) | 0.0009 (5) |
C8 | 0.0209 (6) | 0.0105 (6) | 0.0147 (6) | 0.0009 (5) | 0.0061 (5) | 0.0002 (5) |
C9 | 0.0221 (7) | 0.0119 (6) | 0.0169 (6) | 0.0001 (5) | 0.0070 (5) | −0.0003 (5) |
C10 | 0.0226 (7) | 0.0126 (6) | 0.0160 (6) | −0.0002 (5) | 0.0060 (5) | −0.0020 (5) |
C11 | 0.0239 (7) | 0.0119 (6) | 0.0183 (6) | 0.0021 (5) | 0.0093 (5) | 0.0009 (5) |
C12 | 0.0247 (7) | 0.0203 (7) | 0.0281 (8) | 0.0008 (6) | 0.0133 (6) | 0.0006 (6) |
C13 | 0.0246 (7) | 0.0104 (6) | 0.0167 (6) | 0.0018 (5) | 0.0035 (5) | −0.0010 (5) |
C14 | 0.0325 (8) | 0.0140 (6) | 0.0252 (7) | −0.0015 (6) | 0.0120 (6) | −0.0040 (6) |
C15 | 0.0345 (9) | 0.0163 (7) | 0.0261 (8) | −0.0040 (6) | 0.0119 (7) | −0.0022 (6) |
C16 | 0.0345 (8) | 0.0152 (7) | 0.0228 (7) | 0.0023 (6) | 0.0072 (6) | −0.0050 (6) |
C17 | 0.0334 (8) | 0.0159 (7) | 0.0239 (7) | 0.0010 (6) | 0.0115 (6) | −0.0044 (6) |
S2 | 0.02007 (17) | 0.01438 (16) | 0.02349 (18) | −0.00236 (12) | 0.00731 (14) | 0.00339 (13) |
N2 | 0.0374 (8) | 0.0153 (6) | 0.0300 (7) | 0.0074 (5) | 0.0129 (6) | 0.0050 (5) |
C18 | 0.0182 (6) | 0.0106 (6) | 0.0170 (6) | 0.0009 (5) | 0.0065 (5) | 0.0012 (5) |
C19 | 0.0181 (6) | 0.0125 (6) | 0.0189 (6) | 0.0012 (5) | 0.0071 (5) | 0.0007 (5) |
C20 | 0.0210 (7) | 0.0172 (6) | 0.0211 (7) | 0.0016 (5) | 0.0093 (6) | 0.0014 (5) |
C21 | 0.0267 (8) | 0.0256 (8) | 0.0277 (8) | 0.0050 (6) | 0.0155 (7) | 0.0004 (6) |
C22 | 0.0341 (9) | 0.0271 (8) | 0.0357 (9) | 0.0145 (7) | 0.0151 (8) | 0.0031 (7) |
C23 | 0.0373 (9) | 0.0217 (8) | 0.0303 (8) | 0.0131 (7) | 0.0133 (7) | 0.0077 (6) |
C24 | 0.0262 (7) | 0.0166 (6) | 0.0198 (7) | 0.0040 (5) | 0.0095 (6) | 0.0028 (5) |
C25 | 0.0194 (6) | 0.0115 (6) | 0.0175 (6) | 0.0006 (5) | 0.0083 (5) | 0.0014 (5) |
C26 | 0.0187 (6) | 0.0139 (6) | 0.0197 (7) | 0.0011 (5) | 0.0068 (5) | 0.0018 (5) |
C27 | 0.0205 (7) | 0.0146 (6) | 0.0200 (7) | 0.0015 (5) | 0.0072 (5) | 0.0025 (5) |
C28 | 0.0208 (7) | 0.0135 (6) | 0.0192 (6) | 0.0000 (5) | 0.0089 (5) | 0.0023 (5) |
C29 | 0.0193 (7) | 0.0211 (7) | 0.0224 (7) | 0.0000 (5) | 0.0061 (6) | 0.0040 (6) |
C30 | 0.0275 (7) | 0.0130 (6) | 0.0225 (7) | 0.0016 (5) | 0.0099 (6) | 0.0012 (5) |
C31 | 0.0277 (8) | 0.0176 (7) | 0.0375 (9) | 0.0013 (6) | 0.0040 (7) | 0.0042 (7) |
C32 | 0.0282 (8) | 0.0221 (8) | 0.0364 (9) | 0.0056 (6) | 0.0049 (7) | 0.0045 (7) |
C33 | 0.0344 (10) | 0.0196 (8) | 0.0654 (14) | 0.0023 (7) | 0.0170 (9) | 0.0156 (8) |
C34 | 0.0274 (9) | 0.0193 (8) | 0.0609 (13) | 0.0027 (6) | 0.0143 (8) | 0.0150 (8) |
O1 | 0.0334 (6) | 0.0143 (5) | 0.0250 (6) | 0.0049 (4) | 0.0125 (5) | 0.0054 (4) |
O2 | 0.0335 (6) | 0.0162 (5) | 0.0221 (5) | 0.0065 (4) | 0.0095 (5) | −0.0003 (4) |
O3 | 0.0337 (6) | 0.0202 (5) | 0.0171 (5) | 0.0076 (5) | 0.0108 (5) | −0.0002 (4) |
C35 | 0.0209 (7) | 0.0141 (6) | 0.0202 (7) | 0.0025 (5) | 0.0049 (5) | 0.0023 (5) |
C36 | 0.0178 (6) | 0.0130 (6) | 0.0174 (6) | 0.0029 (5) | 0.0055 (5) | 0.0018 (5) |
C37 | 0.0224 (7) | 0.0152 (6) | 0.0168 (6) | 0.0043 (5) | 0.0071 (5) | 0.0035 (5) |
C38 | 0.0204 (7) | 0.0161 (6) | 0.0159 (6) | 0.0038 (5) | 0.0064 (5) | 0.0010 (5) |
O4 | 0.0326 (6) | 0.0214 (6) | 0.0275 (6) | 0.0114 (5) | 0.0149 (5) | 0.0064 (5) |
O5 | 0.0380 (7) | 0.0154 (5) | 0.0464 (8) | 0.0032 (5) | 0.0049 (6) | 0.0007 (5) |
O6 | 0.0212 (5) | 0.0271 (6) | 0.0334 (6) | 0.0068 (4) | 0.0121 (5) | 0.0098 (5) |
C39 | 0.0312 (8) | 0.0198 (7) | 0.0170 (7) | 0.0081 (6) | 0.0077 (6) | 0.0019 (5) |
C40 | 0.0238 (7) | 0.0161 (6) | 0.0153 (6) | 0.0061 (5) | 0.0067 (5) | 0.0023 (5) |
C41 | 0.0224 (7) | 0.0168 (6) | 0.0176 (6) | 0.0011 (5) | 0.0060 (5) | 0.0024 (5) |
C42 | 0.0203 (7) | 0.0202 (7) | 0.0172 (6) | 0.0050 (5) | 0.0074 (5) | 0.0037 (5) |
S1—C10 | 1.7310 (15) | C20—C21 | 1.390 (2) |
S1—C11 | 1.7206 (14) | C21—H21 | 0.9500 |
N1—C15 | 1.340 (2) | C21—C22 | 1.387 (2) |
N1—C16 | 1.334 (2) | C22—H22 | 0.9500 |
N1—H1 | 0.884 (19) | C22—C23 | 1.394 (3) |
C1—C1i | 1.364 (3) | C23—H23 | 0.9500 |
C1—C2 | 1.4889 (18) | C23—C24 | 1.389 (2) |
C1—C8 | 1.4896 (18) | C24—H24 | 0.9500 |
C2—C3 | 1.398 (2) | C25—C26 | 1.4206 (19) |
C2—C7 | 1.3984 (19) | C25—C28 | 1.380 (2) |
C3—H3 | 0.9500 | C26—H26 | 0.9500 |
C3—C4 | 1.391 (2) | C26—C27 | 1.3721 (19) |
C4—H4 | 0.9500 | C27—C30 | 1.457 (2) |
C4—C5 | 1.390 (2) | C28—C29 | 1.501 (2) |
C5—H5 | 0.9500 | C29—H29A | 0.940 (11) |
C5—C6 | 1.388 (2) | C29—H29B | 0.940 (11) |
C6—H6 | 0.9500 | C29—H29C | 0.940 (11) |
C6—C7 | 1.390 (2) | C30—C31 | 1.390 (2) |
C7—H7 | 0.9500 | C30—C34 | 1.396 (2) |
C8—C9 | 1.4278 (19) | C31—H31 | 0.9500 |
C8—C11 | 1.383 (2) | C31—C32 | 1.379 (2) |
C9—H9 | 0.9500 | C32—H32 | 0.9500 |
C9—C10 | 1.3681 (19) | C33—H33 | 0.9500 |
C10—C13 | 1.4582 (19) | C33—C34 | 1.376 (2) |
C11—C12 | 1.497 (2) | C34—H34 | 0.9500 |
C12—H12A | 0.934 (12) | O1—H1A | 0.841 (19) |
C12—H12B | 0.934 (12) | O1—C35 | 1.2821 (18) |
C12—H12C | 0.934 (12) | O2—C35 | 1.2483 (19) |
C13—C14 | 1.397 (2) | O3—H3B | 0.851 (18) |
C13—C17 | 1.403 (2) | O3—C38 | 1.3654 (17) |
C14—H14 | 0.9500 | O3—H3A | 0.83 (2) |
C14—C15 | 1.382 (2) | C35—C36 | 1.4963 (19) |
C15—H15 | 0.9500 | C36—C37 | 1.393 (2) |
C16—H16 | 0.9500 | C36—C38iii | 1.4042 (19) |
C16—C17 | 1.380 (2) | C37—H37 | 0.9500 |
C17—H17 | 0.9500 | C37—C38 | 1.3875 (19) |
S2—C27 | 1.7326 (15) | O4—H4A | 0.85 (2) |
S2—C28 | 1.7177 (14) | O4—C39 | 1.291 (2) |
N2—C32 | 1.333 (2) | O5—C39 | 1.227 (2) |
N2—C33 | 1.320 (2) | O6—H6A | 0.868 (19) |
N2—H2 | 0.933 (16) | O6—C42 | 1.3637 (18) |
C18—C18ii | 1.363 (3) | C39—C40 | 1.512 (2) |
C18—C19 | 1.4878 (18) | C40—C41 | 1.387 (2) |
C18—C25 | 1.4908 (18) | C40—C42iv | 1.406 (2) |
C19—C20 | 1.399 (2) | C41—H41 | 0.9500 |
C19—C24 | 1.398 (2) | C41—C42 | 1.394 (2) |
C20—H20 | 0.9500 | ||
C11—S1—C10 | 92.68 (7) | C22—C21—H21 | 120.1 |
C15—N1—H1 | 119 (3) | C21—C22—H22 | 120.0 |
C16—N1—C15 | 119.68 (14) | C21—C22—C23 | 120.06 (15) |
C16—N1—H1 | 121 (3) | C23—C22—H22 | 120.0 |
C1i—C1—C2 | 123.67 (7) | C22—C23—H23 | 120.0 |
C1i—C1—C8 | 120.62 (7) | C24—C23—C22 | 120.03 (15) |
C2—C1—C8 | 115.71 (11) | C24—C23—H23 | 120.0 |
C3—C2—C1 | 120.26 (12) | C19—C24—H24 | 119.7 |
C7—C2—C1 | 120.99 (12) | C23—C24—C19 | 120.53 (14) |
C7—C2—C3 | 118.65 (13) | C23—C24—H24 | 119.7 |
C2—C3—H3 | 119.6 | C26—C25—C18 | 123.17 (12) |
C4—C3—C2 | 120.72 (14) | C28—C25—C18 | 124.53 (12) |
C4—C3—H3 | 119.6 | C28—C25—C26 | 112.11 (12) |
C3—C4—H4 | 119.9 | C25—C26—H26 | 123.1 |
C5—C4—C3 | 120.13 (14) | C27—C26—C25 | 113.81 (13) |
C5—C4—H4 | 119.9 | C27—C26—H26 | 123.1 |
C4—C5—H5 | 120.2 | C26—C27—S2 | 110.17 (11) |
C6—C5—C4 | 119.52 (14) | C26—C27—C30 | 127.60 (14) |
C6—C5—H5 | 120.2 | C30—C27—S2 | 122.11 (11) |
C5—C6—H6 | 119.7 | C25—C28—S2 | 111.28 (10) |
C5—C6—C7 | 120.56 (15) | C25—C28—C29 | 129.29 (13) |
C7—C6—H6 | 119.7 | C29—C28—S2 | 119.42 (11) |
C2—C7—H7 | 119.8 | C28—C29—H29A | 109.5 |
C6—C7—C2 | 120.41 (14) | C28—C29—H29B | 109.5 |
C6—C7—H7 | 119.8 | C28—C29—H29C | 109.5 |
C9—C8—C1 | 122.62 (12) | H29A—C29—H29B | 109.5 |
C11—C8—C1 | 125.24 (13) | H29A—C29—H29C | 109.5 |
C11—C8—C9 | 112.06 (12) | H29B—C29—H29C | 109.5 |
C8—C9—H9 | 123.2 | C31—C30—C27 | 121.04 (14) |
C10—C9—C8 | 113.69 (13) | C31—C30—C34 | 117.09 (15) |
C10—C9—H9 | 123.2 | C34—C30—C27 | 121.87 (15) |
C9—C10—S1 | 110.45 (11) | C30—C31—H31 | 120.0 |
C9—C10—C13 | 128.05 (14) | C32—C31—C30 | 120.07 (16) |
C13—C10—S1 | 121.45 (11) | C32—C31—H31 | 120.0 |
C8—C11—S1 | 111.10 (11) | N2—C32—C31 | 120.95 (16) |
C8—C11—C12 | 130.32 (13) | N2—C32—H32 | 119.5 |
C12—C11—S1 | 118.51 (11) | C31—C32—H32 | 119.5 |
C11—C12—H12A | 109.5 | N2—C33—H33 | 119.2 |
C11—C12—H12B | 109.5 | N2—C33—C34 | 121.60 (17) |
C11—C12—H12C | 109.5 | C34—C33—H33 | 119.2 |
H12A—C12—H12B | 109.5 | C30—C34—H34 | 120.1 |
H12A—C12—H12C | 109.5 | C33—C34—C30 | 119.73 (17) |
H12B—C12—H12C | 109.5 | C33—C34—H34 | 120.1 |
C14—C13—C10 | 120.66 (13) | C35—O1—H1A | 112 (4) |
C14—C13—C17 | 117.49 (14) | C38—O3—H3B | 104 (2) |
C17—C13—C10 | 121.84 (14) | C38—O3—H3A | 96 (5) |
C13—C14—H14 | 120.3 | O1—C35—C36 | 116.03 (13) |
C15—C14—C13 | 119.42 (14) | O2—C35—O1 | 124.29 (13) |
C15—C14—H14 | 120.3 | O2—C35—C36 | 119.68 (13) |
N1—C15—C14 | 121.93 (16) | C37—C36—C35 | 120.60 (13) |
N1—C15—H15 | 119.0 | C37—C36—C38iii | 119.52 (12) |
C14—C15—H15 | 119.0 | C38iii—C36—C35 | 119.88 (13) |
N1—C16—H16 | 119.1 | C36—C37—H37 | 119.6 |
N1—C16—C17 | 121.77 (14) | C38—C37—C36 | 120.74 (13) |
C17—C16—H16 | 119.1 | C38—C37—H37 | 119.6 |
C13—C17—H17 | 120.2 | O3—C38—C36iii | 121.60 (13) |
C16—C17—C13 | 119.69 (15) | O3—C38—C37 | 118.64 (13) |
C16—C17—H17 | 120.2 | C37—C38—C36iii | 119.75 (13) |
C28—S2—C27 | 92.60 (7) | C39—O4—H4A | 124 (5) |
C32—N2—H2 | 121.9 (15) | C42—O6—H6A | 106 (3) |
C33—N2—C32 | 120.51 (15) | O4—C39—C40 | 114.80 (14) |
C33—N2—H2 | 117.4 (15) | O5—C39—O4 | 123.99 (15) |
C18ii—C18—C19 | 125.76 (8) | O5—C39—C40 | 121.22 (15) |
C18ii—C18—C25 | 119.21 (7) | C41—C40—C39 | 118.66 (14) |
C19—C18—C25 | 114.98 (11) | C41—C40—C42iv | 119.27 (13) |
C20—C19—C18 | 119.64 (12) | C42iv—C40—C39 | 122.04 (13) |
C24—C19—C18 | 121.35 (13) | C40—C41—H41 | 119.4 |
C24—C19—C20 | 118.70 (13) | C40—C41—C42 | 121.20 (14) |
C19—C20—H20 | 119.5 | C42—C41—H41 | 119.4 |
C21—C20—C19 | 120.91 (14) | O6—C42—C40iv | 122.27 (13) |
C21—C20—H20 | 119.5 | O6—C42—C41 | 118.21 (14) |
C20—C21—H21 | 120.1 | C41—C42—C40iv | 119.52 (13) |
C22—C21—C20 | 119.74 (15) | ||
S1—C10—C13—C14 | −154.72 (12) | C18—C19—C24—C23 | −172.06 (15) |
S1—C10—C13—C17 | 24.4 (2) | C18—C25—C26—C27 | 173.06 (13) |
N1—C16—C17—C13 | −0.5 (2) | C18—C25—C28—S2 | −173.04 (11) |
C1i—C1—C2—C3 | 137.50 (18) | C18—C25—C28—C29 | 5.3 (2) |
C1i—C1—C2—C7 | −46.1 (2) | C19—C18—C25—C26 | 133.35 (14) |
C1i—C1—C8—C9 | −43.5 (2) | C19—C18—C25—C28 | −52.05 (19) |
C1i—C1—C8—C11 | 132.90 (18) | C19—C20—C21—C22 | −0.5 (2) |
C1—C2—C3—C4 | 177.26 (13) | C20—C19—C24—C23 | 1.5 (2) |
C1—C2—C7—C6 | −176.75 (14) | C20—C21—C22—C23 | 1.3 (3) |
C1—C8—C9—C10 | 175.63 (13) | C21—C22—C23—C24 | −0.8 (3) |
C1—C8—C11—S1 | −175.89 (11) | C22—C23—C24—C19 | −0.7 (3) |
C1—C8—C11—C12 | 1.0 (2) | C24—C19—C20—C21 | −1.0 (2) |
C2—C1—C8—C9 | 137.04 (14) | C25—C18—C19—C20 | −38.21 (19) |
C2—C1—C8—C11 | −46.58 (19) | C25—C18—C19—C24 | 135.29 (14) |
C2—C3—C4—C5 | −0.9 (2) | C25—C26—C27—S2 | 1.20 (17) |
C3—C2—C7—C6 | −0.3 (2) | C25—C26—C27—C30 | −174.89 (14) |
C3—C4—C5—C6 | 0.5 (2) | C26—C25—C28—S2 | 2.08 (16) |
C4—C5—C6—C7 | 0.0 (3) | C26—C25—C28—C29 | −179.54 (14) |
C5—C6—C7—C2 | −0.1 (2) | C26—C27—C30—C31 | 5.9 (3) |
C7—C2—C3—C4 | 0.8 (2) | C26—C27—C30—C34 | −174.66 (17) |
C8—C1—C2—C3 | −43.04 (18) | C27—S2—C28—C25 | −1.21 (12) |
C8—C1—C2—C7 | 133.33 (14) | C27—S2—C28—C29 | −179.77 (12) |
C8—C9—C10—S1 | 0.97 (16) | C27—C30—C31—C32 | 177.19 (17) |
C8—C9—C10—C13 | −176.53 (14) | C27—C30—C34—C33 | −177.47 (19) |
C9—C8—C11—S1 | 0.83 (16) | C28—S2—C27—C26 | 0.00 (12) |
C9—C8—C11—C12 | 177.70 (15) | C28—S2—C27—C30 | 176.35 (13) |
C9—C10—C13—C14 | 22.5 (2) | C28—C25—C26—C27 | −2.15 (19) |
C9—C10—C13—C17 | −158.32 (15) | C30—C31—C32—N2 | 0.6 (3) |
C10—S1—C11—C8 | −0.25 (12) | C31—C30—C34—C33 | 2.0 (3) |
C10—S1—C11—C12 | −177.53 (12) | C32—N2—C33—C34 | −1.9 (3) |
C10—C13—C14—C15 | 179.00 (14) | C33—N2—C32—C31 | 1.6 (3) |
C10—C13—C17—C16 | −178.36 (14) | C34—C30—C31—C32 | −2.3 (3) |
C11—S1—C10—C9 | −0.42 (12) | O1—C35—C36—C37 | 11.5 (2) |
C11—S1—C10—C13 | 177.27 (12) | O1—C35—C36—C38iii | −168.60 (14) |
C11—C8—C9—C10 | −1.18 (18) | O2—C35—C36—C37 | −168.14 (14) |
C13—C14—C15—N1 | −0.8 (3) | O2—C35—C36—C38iii | 11.8 (2) |
C14—C13—C17—C16 | 0.8 (2) | C35—C36—C37—C38 | −179.99 (13) |
C15—N1—C16—C17 | −0.6 (2) | C36—C37—C38—O3 | −178.70 (13) |
C16—N1—C15—C14 | 1.2 (2) | C36—C37—C38—C36iii | −0.1 (2) |
C17—C13—C14—C15 | −0.2 (2) | C38iii—C36—C37—C38 | 0.1 (2) |
S2—C27—C30—C31 | −169.77 (13) | O4—C39—C40—C41 | −174.94 (13) |
S2—C27—C30—C34 | 9.7 (2) | O4—C39—C40—C42iv | 7.1 (2) |
N2—C33—C34—C30 | 0.0 (4) | O5—C39—C40—C41 | 4.8 (2) |
C18ii—C18—C19—C20 | 144.55 (19) | O5—C39—C40—C42iv | −173.10 (15) |
C18ii—C18—C19—C24 | −42.0 (3) | C39—C40—C41—C42 | −177.20 (13) |
C18ii—C18—C25—C26 | −49.2 (2) | C40—C41—C42—O6 | 179.87 (13) |
C18ii—C18—C25—C28 | 125.39 (19) | C40—C41—C42—C40iv | −0.8 (2) |
C18—C19—C20—C21 | 172.72 (14) | C42iv—C40—C41—C42 | 0.8 (2) |
Symmetry codes: (i) −x+3/2, y, −z+1/2; (ii) −x+3/2, y, −z+3/2; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1v | 0.88 (2) | 1.65 (2) | 2.5259 (17) | 170 (5) |
N2—H2···O4 | 0.93 (2) | 1.65 (2) | 2.5669 (17) | 169 (2) |
O1—H1A···N1vi | 0.84 (2) | 1.69 (2) | 2.5259 (17) | 174 (6) |
O3—H3B···O2iii | 0.85 (2) | 1.78 (2) | 2.5642 (16) | 153 (3) |
O4—H4A···O6iv | 0.85 (2) | 1.89 (6) | 2.5437 (17) | 132 (6) |
O6—H6A···O4iv | 0.87 (2) | 1.76 (3) | 2.5437 (17) | 150 (4) |
Symmetry codes: (iii) −x+1, −y+1, −z; (iv) −x+1, −y+2, −z+1; (v) −x+3/2, y+1, −z+1/2; (vi) −x+3/2, y−1, −z+1/2. |
4(C34H27.5N2S2)·7(C7H5O4) | Z = 1 |
Mr = 3184.56 | F(000) = 1663 |
Triclinic, P1 | Dx = 1.329 Mg m−3 |
a = 10.602 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.714 (4) Å | Cell parameters from 9921 reflections |
c = 24.181 (5) Å | θ = 2.2–25.2° |
α = 71.454 (6)° | µ = 0.19 mm−1 |
β = 88.132 (6)° | T = 90 K |
γ = 78.607 (6)° | Prism, yellow |
V = 3980.4 (14) Å3 | 0.16 × 0.14 × 0.04 mm |
Bruker APEX-II CCD diffractometer | 9836 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.059 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1544 before and 0.0733 after correction. The Ratio of minimum to maximum transmission is 0.7627. The λ/2 correction factor is Not present. | θmax = 24.7°, θmin = 1.3° |
Tmin = 0.569, Tmax = 0.745 | h = −11→12 |
37926 measured reflections | k = −19→19 |
13567 independent reflections | l = −28→28 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.238 | w = 1/[σ2(Fo2) + (0.0813P)2 + 15.2529P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
13567 reflections | Δρmax = 1.61 e Å−3 |
1176 parameters | Δρmin = −0.46 e Å−3 |
323 restraints |
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) | |
S1 | 0.15445 (14) | 0.43930 (9) | 0.77702 (7) | 0.0381 (4) | |
S2 | −0.23747 (12) | 0.71789 (8) | 0.73557 (6) | 0.0273 (3) | |
N1 | 0.0397 (6) | 0.5015 (5) | 0.5508 (3) | 0.0607 (18) | |
N2 | −0.3493 (4) | 0.9160 (3) | 0.51641 (18) | 0.0263 (9) | |
C1 | 0.1931 (5) | 0.6575 (3) | 0.8049 (2) | 0.0304 (12) | |
C8 | 0.1763 (5) | 0.5861 (3) | 0.7828 (2) | 0.0293 (12) | |
C9 | 0.1505 (5) | 0.5988 (3) | 0.7236 (2) | 0.0306 (12) | |
H9 | 0.144477 | 0.652878 | 0.694018 | 0.037* | |
C10 | 0.1346 (5) | 0.5246 (4) | 0.7127 (2) | 0.0344 (13) | |
C11 | 0.1831 (5) | 0.5027 (3) | 0.8173 (3) | 0.0351 (13) | |
C12 | 0.2079 (7) | 0.4634 (4) | 0.8820 (3) | 0.0470 (16) | |
H12A | 0.300872 | 0.447715 | 0.890563 | 0.070* | |
H12B | 0.170236 | 0.411783 | 0.896344 | 0.070* | |
H12C | 0.168615 | 0.505127 | 0.901439 | 0.070* | |
C13 | 0.1028 (5) | 0.5168 (4) | 0.6570 (3) | 0.0372 (14) | |
C14 | 0.0803 (7) | 0.5856 (5) | 0.6072 (3) | 0.0525 (17) | |
H14 | 0.086719 | 0.640621 | 0.608954 | 0.063* | |
C15 | 0.0490 (7) | 0.5783 (6) | 0.5553 (3) | 0.064 (2) | |
H15 | 0.033487 | 0.628104 | 0.521767 | 0.077* | |
C16 | 0.0626 (6) | 0.4337 (5) | 0.5982 (3) | 0.0542 (19) | |
H16 | 0.055319 | 0.379570 | 0.594883 | 0.065* | |
C17 | 0.0960 (6) | 0.4360 (4) | 0.6516 (3) | 0.0469 (16) | |
H17 | 0.114063 | 0.384958 | 0.684156 | 0.056* | |
C18 | 0.1056 (5) | 0.7324 (3) | 0.7909 (2) | 0.0260 (11) | |
C19 | 0.1240 (5) | 0.8094 (3) | 0.8061 (2) | 0.0255 (11) | |
C20 | 0.0242 (5) | 0.8532 (3) | 0.8303 (2) | 0.0319 (12) | |
H20 | −0.055632 | 0.834596 | 0.836441 | 0.038* | |
C21 | 0.0401 (5) | 0.9244 (4) | 0.8457 (2) | 0.0332 (13) | |
H21 | −0.027718 | 0.953243 | 0.863215 | 0.040* | |
C22 | 0.1556 (5) | 0.9525 (3) | 0.8353 (2) | 0.0294 (12) | |
H22 | 0.166576 | 1.001510 | 0.845042 | 0.035* | |
C23 | 0.2551 (5) | 0.9094 (3) | 0.8107 (2) | 0.0284 (11) | |
H23 | 0.334312 | 0.928817 | 0.803794 | 0.034* | |
C24 | 0.2400 (5) | 0.8377 (3) | 0.7959 (2) | 0.0275 (11) | |
H24 | 0.308499 | 0.808388 | 0.779032 | 0.033* | |
C25 | −0.0182 (5) | 0.7422 (3) | 0.7601 (2) | 0.0250 (11) | |
C26 | −0.0540 (5) | 0.7991 (3) | 0.7033 (2) | 0.0243 (11) | |
H26 | −0.002900 | 0.838299 | 0.681468 | 0.029* | |
C27 | −0.1691 (5) | 0.7927 (3) | 0.6827 (2) | 0.0223 (10) | |
C28 | −0.1098 (5) | 0.6945 (3) | 0.7838 (2) | 0.0287 (11) | |
C29 | −0.1106 (6) | 0.6297 (4) | 0.8429 (2) | 0.0379 (13) | |
H29A | −0.086042 | 0.571598 | 0.839882 | 0.057* | |
H29B | −0.197138 | 0.637306 | 0.858391 | 0.057* | |
H29C | −0.049159 | 0.637749 | 0.869115 | 0.057* | |
C30 | −0.2319 (4) | 0.8357 (3) | 0.6257 (2) | 0.0225 (10) | |
C31 | −0.1981 (5) | 0.9114 (3) | 0.5873 (2) | 0.0259 (11) | |
H31 | −0.134498 | 0.936220 | 0.598854 | 0.031* | |
C32 | −0.2571 (5) | 0.9483 (3) | 0.5339 (2) | 0.0273 (11) | |
H32 | −0.232591 | 0.998357 | 0.507998 | 0.033* | |
C33 | −0.3863 (5) | 0.8450 (3) | 0.5522 (2) | 0.0273 (11) | |
H33 | −0.452947 | 0.823406 | 0.539822 | 0.033* | |
C34 | −0.3286 (5) | 0.8042 (3) | 0.6061 (2) | 0.0268 (11) | |
H34 | −0.354359 | 0.753672 | 0.630621 | 0.032* | |
C2 | 0.312 (3) | 0.635 (2) | 0.8399 (11) | 0.037 (4) | 0.64 (3) |
C3 | 0.435 (2) | 0.6001 (17) | 0.8201 (10) | 0.052 (4) | 0.64 (3) |
H3 | 0.438792 | 0.592514 | 0.782695 | 0.062* | 0.64 (3) |
C4 | 0.5443 (14) | 0.5780 (11) | 0.8531 (10) | 0.068 (4) | 0.64 (3) |
H4 | 0.622640 | 0.553244 | 0.839470 | 0.082* | 0.64 (3) |
C5 | 0.4300 (19) | 0.6269 (11) | 0.9270 (9) | 0.060 (4) | 0.64 (3) |
H5 | 0.429277 | 0.636233 | 0.963792 | 0.072* | 0.64 (3) |
C6 | 0.5425 (18) | 0.5913 (13) | 0.9069 (11) | 0.074 (5) | 0.64 (3) |
H6 | 0.619773 | 0.575559 | 0.929939 | 0.088* | 0.64 (3) |
C7 | 0.3164 (17) | 0.6495 (13) | 0.8930 (9) | 0.046 (4) | 0.64 (3) |
H7 | 0.239539 | 0.675590 | 0.906931 | 0.055* | 0.64 (3) |
C2A | 0.304 (6) | 0.646 (4) | 0.849 (2) | 0.037 (7) | 0.36 (3) |
C3A | 0.421 (4) | 0.611 (3) | 0.8369 (14) | 0.043 (6) | 0.36 (3) |
H3A | 0.435681 | 0.599152 | 0.800971 | 0.051* | 0.36 (3) |
C4A | 0.522 (3) | 0.591 (2) | 0.8786 (14) | 0.060 (6) | 0.36 (3) |
H4A | 0.607136 | 0.568977 | 0.870447 | 0.071* | 0.36 (3) |
C5A | 0.494 (4) | 0.606 (2) | 0.9331 (16) | 0.059 (7) | 0.36 (3) |
H5A | 0.560867 | 0.598553 | 0.960228 | 0.071* | 0.36 (3) |
C6A | 0.366 (3) | 0.6298 (14) | 0.9458 (11) | 0.050 (6) | 0.36 (3) |
H6A | 0.345523 | 0.629924 | 0.984327 | 0.060* | 0.36 (3) |
C7A | 0.269 (3) | 0.654 (2) | 0.9044 (14) | 0.042 (6) | 0.36 (3) |
H7A | 0.182482 | 0.674531 | 0.912325 | 0.051* | 0.36 (3) |
S3 | 0.17467 (12) | 0.20076 (8) | 0.79479 (6) | 0.0270 (3) | |
S4 | 0.50685 (13) | 0.39740 (10) | 0.76560 (7) | 0.0373 (4) | |
N3 | 0.0661 (4) | 0.1029 (3) | 0.6165 (2) | 0.0319 (11) | |
N4 | 0.4067 (4) | 0.4081 (3) | 0.5461 (2) | 0.0364 (11) | |
C35 | 0.5297 (5) | 0.0886 (4) | 0.8644 (2) | 0.0271 (11) | |
C36 | 0.5633 (5) | −0.0060 (4) | 0.8962 (2) | 0.0339 (13) | |
C37 | 0.4697 (6) | −0.0553 (4) | 0.9048 (2) | 0.0398 (14) | |
H37 | 0.382588 | −0.027442 | 0.894590 | 0.048* | |
C38 | 0.4988 (7) | −0.1434 (4) | 0.9277 (3) | 0.0480 (16) | |
H38 | 0.432065 | −0.175297 | 0.932362 | 0.058* | |
C39 | 0.6225 (7) | −0.1860 (5) | 0.9438 (3) | 0.0574 (19) | |
H39 | 0.642121 | −0.246950 | 0.959764 | 0.069* | |
C40 | 0.7168 (7) | −0.1396 (5) | 0.9367 (3) | 0.063 (2) | |
H40 | 0.802912 | −0.168604 | 0.948274 | 0.076* | |
C41 | 0.6899 (6) | −0.0506 (5) | 0.9128 (3) | 0.0500 (17) | |
H41 | 0.757836 | −0.019653 | 0.907692 | 0.060* | |
C42 | 0.4038 (5) | 0.1190 (3) | 0.8301 (2) | 0.0261 (11) | |
C43 | 0.3762 (4) | 0.0977 (3) | 0.7807 (2) | 0.0228 (10) | |
H43 | 0.435750 | 0.059854 | 0.765670 | 0.027* | |
C44 | 0.2554 (4) | 0.1363 (3) | 0.7559 (2) | 0.0214 (10) | |
C45 | 0.3024 (5) | 0.1742 (3) | 0.8436 (2) | 0.0275 (11) | |
C46 | 0.2932 (5) | 0.2130 (4) | 0.8921 (2) | 0.0394 (14) | |
H46A | 0.317283 | 0.269609 | 0.877877 | 0.059* | |
H46B | 0.351617 | 0.175309 | 0.924616 | 0.059* | |
H46C | 0.204665 | 0.219513 | 0.905558 | 0.059* | |
C47 | 0.1906 (5) | 0.1259 (3) | 0.7073 (2) | 0.0256 (11) | |
C48 | 0.2487 (5) | 0.0688 (3) | 0.6778 (2) | 0.0276 (11) | |
H48 | 0.333232 | 0.036483 | 0.689290 | 0.033* | |
C49 | 0.1854 (5) | 0.0593 (3) | 0.6331 (2) | 0.0297 (12) | |
H49 | 0.226863 | 0.020911 | 0.613339 | 0.036* | |
C50 | 0.0054 (6) | 0.1588 (4) | 0.6427 (3) | 0.0489 (17) | |
H50 | −0.079167 | 0.190090 | 0.629935 | 0.059* | |
C51 | 0.0663 (5) | 0.1705 (4) | 0.6883 (3) | 0.0424 (15) | |
H51 | 0.022596 | 0.209631 | 0.706970 | 0.051* | |
C52 | 0.6018 (5) | 0.1472 (4) | 0.8635 (2) | 0.0306 (12) | |
C53 | 0.7149 (5) | 0.1311 (4) | 0.9034 (2) | 0.0386 (14) | |
C54 | 0.8339 (6) | 0.1439 (4) | 0.8811 (3) | 0.0468 (16) | |
H54 | 0.842895 | 0.163380 | 0.839963 | 0.056* | |
C55 | 0.9399 (6) | 0.1290 (5) | 0.9174 (3) | 0.062 (2) | |
H55 | 1.021883 | 0.134979 | 0.901451 | 0.074* | |
C56 | 0.9257 (7) | 0.1054 (6) | 0.9769 (3) | 0.079 (3) | |
H56 | 0.997330 | 0.096543 | 1.002234 | 0.094* | |
C57 | 0.8070 (7) | 0.0948 (7) | 0.9994 (3) | 0.081 (3) | |
H57 | 0.796662 | 0.078883 | 1.040416 | 0.098* | |
C58 | 0.7029 (6) | 0.1071 (5) | 0.9627 (3) | 0.058 (2) | |
H58 | 0.621755 | 0.098765 | 0.978876 | 0.070* | |
C59 | 0.5699 (5) | 0.2344 (4) | 0.8191 (2) | 0.0298 (12) | |
C60 | 0.5488 (4) | 0.2454 (3) | 0.7599 (2) | 0.0261 (11) | |
H60 | 0.559537 | 0.198169 | 0.745167 | 0.031* | |
C61 | 0.5117 (5) | 0.3288 (3) | 0.7249 (2) | 0.0289 (12) | |
C62 | 0.5541 (5) | 0.3129 (4) | 0.8289 (3) | 0.0372 (14) | |
C63 | 0.5718 (6) | 0.3318 (5) | 0.8842 (3) | 0.0532 (18) | |
H63A | 0.663328 | 0.329425 | 0.890884 | 0.080* | |
H63B | 0.540873 | 0.288980 | 0.916890 | 0.080* | |
H63C | 0.522833 | 0.389366 | 0.881102 | 0.080* | |
C64 | 0.4786 (5) | 0.3578 (3) | 0.6629 (2) | 0.0297 (12) | |
C65 | 0.4901 (6) | 0.2990 (4) | 0.6322 (2) | 0.0370 (13) | |
H65 | 0.523893 | 0.239834 | 0.651760 | 0.044* | |
C66 | 0.4539 (6) | 0.3245 (4) | 0.5750 (3) | 0.0390 (14) | |
H66 | 0.461800 | 0.283124 | 0.555133 | 0.047* | |
C67 | 0.3955 (5) | 0.4676 (3) | 0.5727 (2) | 0.0327 (12) | |
H67 | 0.363143 | 0.526288 | 0.551464 | 0.039* | 0.5 |
C68 | 0.4305 (5) | 0.4446 (4) | 0.6310 (3) | 0.0350 (13) | |
H68 | 0.422144 | 0.487471 | 0.649629 | 0.042* | |
O1 | 0.4587 (3) | 0.0030 (2) | 0.58971 (14) | 0.0266 (8) | |
O2 | 0.5564 (4) | 0.1146 (3) | 0.56341 (18) | 0.0411 (10) | |
O3 | 0.4930 (4) | −0.1044 (3) | 0.69316 (16) | 0.0375 (9) | |
O4 | 0.7164 (5) | 0.1301 (4) | 0.6325 (3) | 0.0672 (15) | |
C69 | 0.5342 (5) | 0.0469 (3) | 0.6005 (2) | 0.0303 (12) | |
C70 | 0.5969 (5) | 0.0169 (4) | 0.6593 (2) | 0.0345 (13) | |
C71 | 0.5731 (5) | −0.0567 (4) | 0.7033 (2) | 0.0388 (15) | |
C72 | 0.6291 (6) | −0.0821 (5) | 0.7584 (3) | 0.0517 (19) | |
H72 | 0.610129 | −0.130802 | 0.788098 | 0.062* | |
C73 | 0.7129 (7) | −0.0355 (7) | 0.7697 (4) | 0.075 (3) | |
H73 | 0.751739 | −0.052897 | 0.807610 | 0.090* | |
C74 | 0.7414 (7) | 0.0339 (6) | 0.7285 (4) | 0.066 (2) | |
H74 | 0.800220 | 0.064437 | 0.737600 | 0.079* | |
C75 | 0.6852 (6) | 0.0611 (5) | 0.6729 (3) | 0.0509 (18) | |
O5 | 0.0548 (3) | 0.8942 (2) | 0.48399 (15) | 0.0317 (8) | |
O6 | 0.1426 (4) | 0.7681 (3) | 0.47185 (18) | 0.0492 (12) | |
O7 | 0.1070 (3) | 0.9212 (2) | 0.57804 (15) | 0.0274 (8) | |
O8 | 0.3401 (4) | 0.6738 (3) | 0.53163 (18) | 0.0417 (10) | |
C76 | 0.1337 (5) | 0.8214 (3) | 0.4993 (2) | 0.0324 (12) | |
C77 | 0.2171 (5) | 0.7981 (3) | 0.5521 (2) | 0.0266 (11) | |
C78 | 0.1994 (5) | 0.8473 (3) | 0.5904 (2) | 0.0238 (11) | |
C79 | 0.2725 (5) | 0.8237 (3) | 0.6416 (2) | 0.0294 (12) | |
H79 | 0.256771 | 0.856443 | 0.667678 | 0.035* | |
C80 | 0.3702 (5) | 0.7501 (3) | 0.6537 (2) | 0.0303 (12) | |
H80 | 0.423140 | 0.734135 | 0.687957 | 0.036* | |
C81 | 0.3916 (5) | 0.7001 (3) | 0.6174 (2) | 0.0322 (12) | |
H81 | 0.457540 | 0.649795 | 0.626925 | 0.039* | |
C82 | 0.3161 (5) | 0.7238 (3) | 0.5667 (2) | 0.0303 (12) | |
O9 | 0.6826 (4) | 0.5618 (2) | 0.55902 (17) | 0.0433 (10) | |
O10 | 0.7240 (4) | 0.4253 (3) | 0.55960 (17) | 0.0398 (9) | |
O11 | 0.7261 (4) | 0.5994 (2) | 0.64842 (19) | 0.0464 (11) | |
O12 | 0.7989 (4) | 0.3040 (2) | 0.65380 (18) | 0.0389 (9) | |
C83 | 0.7208 (5) | 0.4798 (4) | 0.5854 (3) | 0.0348 (13) | |
C84 | 0.7604 (5) | 0.4537 (3) | 0.6471 (2) | 0.0282 (11) | |
C85 | 0.7626 (5) | 0.5134 (3) | 0.6765 (2) | 0.0322 (12) | |
C86 | 0.8030 (5) | 0.4870 (3) | 0.7344 (2) | 0.0346 (13) | |
H86 | 0.804692 | 0.528277 | 0.753621 | 0.042* | |
C87 | 0.8410 (5) | 0.3998 (4) | 0.7643 (2) | 0.0328 (12) | |
H87 | 0.869048 | 0.381681 | 0.804040 | 0.039* | |
C88 | 0.8385 (5) | 0.3394 (3) | 0.7372 (2) | 0.0307 (12) | |
H88 | 0.863857 | 0.279871 | 0.758299 | 0.037* | |
C89 | 0.7993 (5) | 0.3649 (3) | 0.6795 (2) | 0.0305 (12) | |
H15A | 1.209 (13) | 0.400 (6) | 1.010 (6) | 0.037* | 0.5 |
H16A | 0.843 (9) | 0.589 (8) | 0.974 (6) | 0.037* | 0.5 |
O13 | 1.1593 (17) | 0.5064 (9) | 1.0225 (5) | 0.063 (5) | 0.5 |
O14 | 0.9801 (13) | 0.6044 (9) | 0.9992 (6) | 0.072 (5) | 0.5 |
O15 | 1.1742 (9) | 0.3566 (7) | 1.0176 (4) | 0.061 (3) | 0.5 |
H1 | 0.009 (17) | 0.503 (13) | 0.517 (4) | 0.073* | 0.5 |
H2 | −0.384 (7) | 0.938 (5) | 0.4804 (15) | 0.073* | |
H3B | 0.027 (6) | 0.107 (5) | 0.5837 (19) | 0.073* | |
H4B | 0.377 (7) | 0.425 (5) | 0.5090 (14) | 0.073* | |
H3C | 0.467 (7) | −0.087 (5) | 0.6579 (13) | 0.073* | |
H4C | 0.672 (7) | 0.151 (5) | 0.601 (2) | 0.073* | |
H7B | 0.074 (7) | 0.923 (5) | 0.5462 (19) | 0.073* | |
H8 | 0.278 (5) | 0.697 (5) | 0.507 (3) | 0.073* | |
H11 | 0.709 (7) | 0.608 (5) | 0.6128 (13) | 0.073* | |
H12 | 0.774 (7) | 0.329 (5) | 0.6181 (13) | 0.073* | |
O16 | 0.7817 (10) | 0.5666 (7) | 0.9696 (4) | 0.065 (3) | 0.5 |
C90 | 1.039 (2) | 0.5289 (11) | 1.0049 (7) | 0.044 (4) | 0.5 |
C91 | 0.980 (2) | 0.4651 (12) | 0.9931 (9) | 0.066 (7) | 0.5 |
C92 | 1.0467 (15) | 0.3808 (12) | 1.0012 (7) | 0.052 (4) | 0.5 |
C93 | 0.9894 (12) | 0.3202 (9) | 0.9863 (6) | 0.067 (4) | 0.5 |
H93 | 1.036476 | 0.264310 | 0.989312 | 0.080* | 0.5 |
C94 | 0.8624 (13) | 0.3463 (9) | 0.9671 (6) | 0.076 (5) | 0.5 |
H94 | 0.821443 | 0.306373 | 0.957763 | 0.091* | 0.5 |
C95 | 0.7923 (14) | 0.4270 (9) | 0.9609 (6) | 0.074 (4) | 0.5 |
H95 | 0.704265 | 0.441163 | 0.948615 | 0.088* | 0.5 |
C96 | 0.849 (2) | 0.4882 (11) | 0.9725 (8) | 0.053 (5) | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0336 (8) | 0.0224 (7) | 0.0638 (10) | −0.0055 (6) | 0.0015 (7) | −0.0212 (7) |
S2 | 0.0279 (7) | 0.0253 (7) | 0.0299 (7) | −0.0098 (5) | 0.0001 (5) | −0.0076 (6) |
N1 | 0.048 (3) | 0.104 (5) | 0.064 (4) | −0.043 (4) | 0.024 (3) | −0.058 (4) |
N2 | 0.024 (2) | 0.025 (2) | 0.028 (2) | −0.0023 (18) | 0.0006 (18) | −0.008 (2) |
C1 | 0.035 (3) | 0.022 (3) | 0.034 (3) | −0.009 (2) | 0.002 (2) | −0.007 (2) |
C8 | 0.023 (3) | 0.022 (3) | 0.046 (3) | −0.004 (2) | 0.003 (2) | −0.015 (2) |
C9 | 0.022 (3) | 0.024 (3) | 0.049 (3) | −0.006 (2) | 0.005 (2) | −0.015 (3) |
C10 | 0.025 (3) | 0.036 (3) | 0.048 (3) | −0.008 (2) | 0.010 (2) | −0.022 (3) |
C11 | 0.030 (3) | 0.025 (3) | 0.052 (4) | −0.005 (2) | 0.001 (2) | −0.015 (3) |
C12 | 0.060 (4) | 0.031 (3) | 0.048 (4) | −0.013 (3) | −0.006 (3) | −0.007 (3) |
C13 | 0.023 (3) | 0.049 (4) | 0.053 (4) | −0.017 (3) | 0.015 (2) | −0.031 (3) |
C14 | 0.061 (4) | 0.061 (5) | 0.052 (4) | −0.026 (4) | 0.008 (3) | −0.033 (4) |
C15 | 0.072 (5) | 0.080 (6) | 0.061 (5) | −0.040 (4) | 0.008 (4) | −0.036 (4) |
C16 | 0.046 (4) | 0.071 (5) | 0.078 (5) | −0.034 (4) | 0.028 (4) | −0.057 (5) |
C17 | 0.038 (3) | 0.052 (4) | 0.069 (4) | −0.021 (3) | 0.023 (3) | −0.039 (4) |
C18 | 0.031 (3) | 0.023 (3) | 0.026 (3) | −0.007 (2) | 0.003 (2) | −0.009 (2) |
C19 | 0.029 (3) | 0.021 (3) | 0.026 (3) | −0.006 (2) | −0.005 (2) | −0.005 (2) |
C20 | 0.027 (3) | 0.032 (3) | 0.040 (3) | −0.009 (2) | −0.001 (2) | −0.013 (3) |
C21 | 0.033 (3) | 0.034 (3) | 0.034 (3) | 0.001 (2) | −0.003 (2) | −0.018 (3) |
C22 | 0.040 (3) | 0.021 (3) | 0.030 (3) | −0.008 (2) | −0.004 (2) | −0.010 (2) |
C23 | 0.029 (3) | 0.022 (3) | 0.034 (3) | −0.006 (2) | −0.001 (2) | −0.008 (2) |
C24 | 0.030 (3) | 0.022 (3) | 0.028 (3) | 0.000 (2) | −0.001 (2) | −0.009 (2) |
C25 | 0.025 (3) | 0.025 (3) | 0.030 (3) | −0.005 (2) | 0.003 (2) | −0.016 (2) |
C26 | 0.030 (3) | 0.020 (3) | 0.027 (3) | −0.009 (2) | 0.006 (2) | −0.012 (2) |
C27 | 0.026 (3) | 0.015 (2) | 0.028 (3) | −0.004 (2) | 0.002 (2) | −0.010 (2) |
C28 | 0.032 (3) | 0.026 (3) | 0.031 (3) | −0.011 (2) | 0.001 (2) | −0.011 (2) |
C29 | 0.044 (3) | 0.035 (3) | 0.031 (3) | −0.013 (3) | −0.003 (2) | −0.002 (3) |
C30 | 0.023 (2) | 0.017 (2) | 0.027 (3) | 0.001 (2) | 0.003 (2) | −0.010 (2) |
C31 | 0.025 (3) | 0.025 (3) | 0.030 (3) | −0.007 (2) | 0.004 (2) | −0.010 (2) |
C32 | 0.032 (3) | 0.018 (3) | 0.032 (3) | −0.004 (2) | 0.004 (2) | −0.008 (2) |
C33 | 0.027 (3) | 0.022 (3) | 0.033 (3) | −0.003 (2) | −0.002 (2) | −0.011 (2) |
C34 | 0.036 (3) | 0.016 (2) | 0.031 (3) | −0.007 (2) | 0.004 (2) | −0.010 (2) |
C2 | 0.040 (7) | 0.017 (8) | 0.058 (10) | −0.013 (6) | −0.010 (7) | −0.011 (6) |
C3 | 0.034 (7) | 0.040 (7) | 0.084 (11) | −0.013 (5) | −0.002 (7) | −0.018 (8) |
C4 | 0.034 (6) | 0.064 (8) | 0.112 (12) | −0.011 (5) | 0.001 (7) | −0.035 (8) |
C5 | 0.045 (10) | 0.069 (9) | 0.076 (9) | −0.023 (8) | −0.017 (7) | −0.030 (7) |
C6 | 0.045 (7) | 0.078 (9) | 0.109 (12) | −0.021 (7) | −0.011 (8) | −0.038 (10) |
C7 | 0.052 (7) | 0.029 (6) | 0.055 (8) | −0.008 (7) | −0.015 (7) | −0.009 (6) |
C2A | 0.040 (9) | 0.021 (15) | 0.048 (11) | −0.004 (10) | −0.017 (10) | −0.009 (11) |
C3A | 0.030 (10) | 0.039 (13) | 0.054 (11) | −0.021 (8) | −0.003 (9) | 0.001 (10) |
C4A | 0.041 (10) | 0.066 (13) | 0.066 (14) | −0.014 (10) | −0.016 (8) | −0.010 (12) |
C5A | 0.047 (12) | 0.063 (14) | 0.071 (12) | −0.023 (12) | −0.023 (11) | −0.016 (11) |
C6A | 0.053 (13) | 0.043 (10) | 0.049 (10) | −0.012 (10) | −0.023 (8) | −0.004 (9) |
C7A | 0.051 (11) | 0.029 (9) | 0.045 (11) | 0.000 (12) | −0.026 (9) | −0.012 (9) |
S3 | 0.0230 (6) | 0.0279 (7) | 0.0351 (7) | −0.0027 (5) | −0.0012 (5) | −0.0183 (6) |
S4 | 0.0294 (7) | 0.0345 (8) | 0.0550 (9) | −0.0071 (6) | 0.0044 (6) | −0.0238 (7) |
N3 | 0.027 (2) | 0.035 (3) | 0.041 (3) | 0.002 (2) | −0.0094 (19) | −0.025 (2) |
N4 | 0.033 (3) | 0.031 (3) | 0.040 (3) | −0.004 (2) | −0.005 (2) | −0.005 (2) |
C35 | 0.023 (3) | 0.040 (3) | 0.020 (2) | −0.008 (2) | 0.0003 (19) | −0.012 (2) |
C36 | 0.030 (3) | 0.041 (3) | 0.028 (3) | 0.000 (3) | −0.002 (2) | −0.012 (3) |
C37 | 0.038 (3) | 0.042 (4) | 0.036 (3) | −0.009 (3) | −0.006 (2) | −0.007 (3) |
C38 | 0.062 (4) | 0.035 (4) | 0.045 (4) | −0.014 (3) | −0.003 (3) | −0.007 (3) |
C39 | 0.069 (5) | 0.043 (4) | 0.044 (4) | 0.008 (4) | 0.004 (3) | −0.003 (3) |
C40 | 0.051 (4) | 0.057 (5) | 0.056 (4) | 0.017 (4) | 0.006 (3) | −0.001 (4) |
C41 | 0.035 (3) | 0.056 (4) | 0.045 (4) | 0.001 (3) | 0.005 (3) | −0.003 (3) |
C42 | 0.024 (3) | 0.031 (3) | 0.024 (3) | −0.007 (2) | 0.000 (2) | −0.009 (2) |
C43 | 0.020 (2) | 0.020 (3) | 0.030 (3) | −0.004 (2) | 0.000 (2) | −0.010 (2) |
C44 | 0.022 (2) | 0.016 (2) | 0.027 (3) | −0.0027 (19) | −0.0011 (19) | −0.009 (2) |
C45 | 0.025 (3) | 0.033 (3) | 0.030 (3) | −0.009 (2) | 0.001 (2) | −0.016 (2) |
C46 | 0.031 (3) | 0.058 (4) | 0.041 (3) | −0.009 (3) | 0.002 (2) | −0.031 (3) |
C47 | 0.023 (3) | 0.022 (3) | 0.032 (3) | −0.002 (2) | 0.000 (2) | −0.011 (2) |
C48 | 0.023 (3) | 0.026 (3) | 0.035 (3) | 0.005 (2) | −0.006 (2) | −0.017 (2) |
C49 | 0.024 (3) | 0.024 (3) | 0.042 (3) | 0.007 (2) | −0.006 (2) | −0.018 (2) |
C50 | 0.027 (3) | 0.061 (4) | 0.066 (4) | 0.021 (3) | −0.017 (3) | −0.045 (4) |
C51 | 0.035 (3) | 0.046 (4) | 0.051 (4) | 0.014 (3) | −0.014 (3) | −0.034 (3) |
C52 | 0.021 (3) | 0.047 (3) | 0.026 (3) | −0.009 (2) | 0.002 (2) | −0.014 (2) |
C53 | 0.032 (3) | 0.060 (4) | 0.027 (3) | −0.019 (3) | −0.001 (2) | −0.011 (3) |
C54 | 0.032 (3) | 0.066 (4) | 0.037 (3) | −0.023 (3) | −0.005 (2) | 0.001 (3) |
C55 | 0.037 (4) | 0.091 (6) | 0.049 (4) | −0.036 (4) | −0.009 (3) | 0.004 (4) |
C56 | 0.055 (5) | 0.126 (8) | 0.050 (4) | −0.050 (5) | −0.017 (3) | 0.001 (5) |
C57 | 0.063 (5) | 0.149 (9) | 0.033 (4) | −0.052 (5) | −0.010 (3) | −0.009 (5) |
C58 | 0.041 (4) | 0.102 (6) | 0.033 (3) | −0.028 (4) | −0.003 (3) | −0.014 (4) |
C59 | 0.020 (3) | 0.036 (3) | 0.039 (3) | −0.012 (2) | 0.002 (2) | −0.015 (3) |
C60 | 0.020 (2) | 0.027 (3) | 0.034 (3) | −0.009 (2) | 0.003 (2) | −0.011 (2) |
C61 | 0.021 (3) | 0.024 (3) | 0.044 (3) | −0.005 (2) | 0.001 (2) | −0.013 (2) |
C62 | 0.023 (3) | 0.054 (4) | 0.046 (3) | −0.014 (3) | 0.004 (2) | −0.028 (3) |
C63 | 0.048 (4) | 0.072 (5) | 0.057 (4) | −0.016 (3) | 0.003 (3) | −0.042 (4) |
C64 | 0.016 (2) | 0.023 (3) | 0.047 (3) | −0.006 (2) | −0.003 (2) | −0.005 (2) |
C65 | 0.044 (3) | 0.026 (3) | 0.033 (3) | 0.001 (3) | −0.009 (2) | −0.003 (2) |
C66 | 0.041 (3) | 0.026 (3) | 0.045 (3) | −0.001 (3) | −0.010 (3) | −0.007 (3) |
C67 | 0.027 (3) | 0.022 (3) | 0.043 (3) | −0.001 (2) | −0.002 (2) | −0.004 (2) |
C68 | 0.024 (3) | 0.028 (3) | 0.051 (4) | −0.003 (2) | 0.002 (2) | −0.010 (3) |
O1 | 0.0253 (18) | 0.0251 (19) | 0.0308 (19) | −0.0036 (15) | −0.0018 (14) | −0.0113 (16) |
O2 | 0.043 (2) | 0.034 (2) | 0.052 (3) | −0.0123 (19) | 0.0005 (19) | −0.018 (2) |
O3 | 0.034 (2) | 0.042 (2) | 0.029 (2) | 0.0045 (18) | −0.0015 (17) | −0.0079 (19) |
O4 | 0.050 (3) | 0.058 (3) | 0.116 (5) | −0.016 (3) | −0.011 (3) | −0.053 (4) |
C69 | 0.031 (3) | 0.023 (3) | 0.037 (3) | 0.000 (2) | 0.004 (2) | −0.013 (3) |
C70 | 0.021 (3) | 0.045 (4) | 0.045 (3) | 0.004 (2) | −0.004 (2) | −0.031 (3) |
C71 | 0.028 (3) | 0.050 (4) | 0.035 (3) | 0.017 (3) | −0.002 (2) | −0.023 (3) |
C72 | 0.041 (4) | 0.065 (5) | 0.042 (4) | 0.029 (3) | −0.014 (3) | −0.028 (3) |
C73 | 0.049 (4) | 0.119 (8) | 0.054 (5) | 0.045 (5) | −0.024 (4) | −0.060 (5) |
C74 | 0.039 (4) | 0.102 (7) | 0.080 (6) | 0.012 (4) | −0.024 (4) | −0.074 (6) |
C75 | 0.026 (3) | 0.056 (4) | 0.083 (5) | 0.007 (3) | −0.008 (3) | −0.048 (4) |
O5 | 0.031 (2) | 0.028 (2) | 0.036 (2) | 0.0038 (16) | −0.0109 (16) | −0.0150 (17) |
O6 | 0.064 (3) | 0.033 (2) | 0.052 (3) | 0.013 (2) | −0.026 (2) | −0.026 (2) |
O7 | 0.0246 (18) | 0.0239 (19) | 0.033 (2) | 0.0012 (15) | −0.0044 (15) | −0.0116 (16) |
O8 | 0.043 (2) | 0.031 (2) | 0.051 (3) | 0.0062 (18) | −0.0101 (19) | −0.020 (2) |
C76 | 0.037 (3) | 0.027 (3) | 0.031 (3) | −0.001 (2) | −0.002 (2) | −0.011 (2) |
C77 | 0.026 (3) | 0.021 (3) | 0.031 (3) | −0.003 (2) | −0.001 (2) | −0.008 (2) |
C78 | 0.022 (2) | 0.021 (3) | 0.027 (3) | −0.004 (2) | 0.001 (2) | −0.005 (2) |
C79 | 0.023 (3) | 0.025 (3) | 0.039 (3) | −0.007 (2) | −0.007 (2) | −0.007 (2) |
C80 | 0.028 (3) | 0.032 (3) | 0.029 (3) | −0.010 (2) | −0.006 (2) | −0.003 (2) |
C81 | 0.027 (3) | 0.020 (3) | 0.045 (3) | −0.001 (2) | −0.006 (2) | −0.006 (2) |
C82 | 0.027 (3) | 0.024 (3) | 0.041 (3) | −0.006 (2) | 0.001 (2) | −0.012 (2) |
O9 | 0.049 (3) | 0.029 (2) | 0.045 (2) | 0.0031 (19) | −0.0153 (19) | −0.0068 (19) |
O10 | 0.039 (2) | 0.038 (2) | 0.047 (2) | −0.0036 (18) | −0.0024 (18) | −0.023 (2) |
O11 | 0.066 (3) | 0.017 (2) | 0.052 (3) | 0.0033 (19) | −0.019 (2) | −0.010 (2) |
O12 | 0.038 (2) | 0.025 (2) | 0.056 (3) | 0.0012 (17) | 0.0005 (19) | −0.021 (2) |
C83 | 0.024 (3) | 0.028 (3) | 0.050 (3) | 0.002 (2) | −0.006 (2) | −0.013 (3) |
C84 | 0.024 (3) | 0.022 (3) | 0.040 (3) | −0.002 (2) | −0.003 (2) | −0.011 (2) |
C85 | 0.032 (3) | 0.016 (3) | 0.048 (3) | −0.003 (2) | −0.007 (2) | −0.010 (2) |
C86 | 0.035 (3) | 0.024 (3) | 0.047 (3) | −0.004 (2) | −0.008 (2) | −0.013 (3) |
C87 | 0.024 (3) | 0.031 (3) | 0.038 (3) | −0.005 (2) | −0.003 (2) | −0.005 (3) |
C88 | 0.026 (3) | 0.020 (3) | 0.040 (3) | 0.001 (2) | 0.004 (2) | −0.004 (2) |
C89 | 0.016 (2) | 0.025 (3) | 0.051 (3) | 0.001 (2) | 0.005 (2) | −0.016 (3) |
O13 | 0.059 (6) | 0.055 (8) | 0.071 (12) | 0.004 (5) | −0.004 (6) | −0.025 (8) |
O14 | 0.065 (7) | 0.050 (6) | 0.089 (12) | 0.000 (5) | 0.006 (6) | −0.009 (6) |
O15 | 0.058 (5) | 0.052 (6) | 0.063 (6) | 0.017 (4) | −0.018 (4) | −0.022 (5) |
O16 | 0.045 (5) | 0.053 (6) | 0.073 (7) | 0.012 (4) | −0.003 (5) | 0.001 (5) |
C90 | 0.054 (6) | 0.047 (6) | 0.018 (8) | 0.000 (5) | 0.011 (5) | 0.003 (5) |
C91 | 0.053 (6) | 0.050 (6) | 0.084 (19) | 0.011 (4) | −0.013 (7) | −0.015 (7) |
C92 | 0.058 (6) | 0.046 (6) | 0.032 (10) | 0.010 (5) | −0.015 (6) | 0.002 (5) |
C93 | 0.065 (7) | 0.052 (7) | 0.070 (9) | 0.015 (5) | −0.033 (6) | −0.013 (6) |
C94 | 0.070 (7) | 0.052 (7) | 0.086 (11) | 0.013 (5) | −0.047 (7) | −0.004 (6) |
C95 | 0.062 (7) | 0.051 (6) | 0.086 (11) | 0.003 (5) | −0.024 (7) | 0.002 (6) |
C96 | 0.047 (6) | 0.050 (7) | 0.040 (12) | 0.003 (5) | 0.002 (6) | 0.007 (7) |
S1—C10 | 1.729 (6) | C43—H43 | 0.9500 |
S1—C11 | 1.721 (6) | C43—C44 | 1.376 (7) |
S2—C27 | 1.733 (5) | C44—C47 | 1.455 (7) |
S2—C28 | 1.718 (5) | C45—C46 | 1.503 (7) |
N1—C15 | 1.346 (10) | C46—H46A | 0.9800 |
N1—C16 | 1.319 (10) | C46—H46B | 0.9800 |
N1—H1 | 0.88 (2) | C46—H46C | 0.9800 |
N2—C32 | 1.342 (7) | C47—C48 | 1.403 (7) |
N2—C33 | 1.349 (7) | C47—C51 | 1.392 (7) |
N2—H2 | 0.89 (2) | C48—H48 | 0.9500 |
C1—C8 | 1.495 (7) | C48—C49 | 1.358 (7) |
C1—C18 | 1.354 (7) | C49—H49 | 0.9500 |
C1—C2 | 1.46 (3) | C50—H50 | 0.9500 |
C1—C2A | 1.56 (5) | C50—C51 | 1.379 (8) |
C8—C9 | 1.406 (8) | C51—H51 | 0.9500 |
C8—C11 | 1.367 (8) | C52—C53 | 1.491 (7) |
C9—H9 | 0.9500 | C52—C59 | 1.492 (8) |
C9—C10 | 1.390 (7) | C53—C54 | 1.385 (8) |
C10—C13 | 1.448 (8) | C53—C58 | 1.371 (8) |
C11—C12 | 1.503 (8) | C54—H54 | 0.9500 |
C12—H12A | 0.9800 | C54—C55 | 1.382 (8) |
C12—H12B | 0.9800 | C55—H55 | 0.9500 |
C12—H12C | 0.9800 | C55—C56 | 1.377 (10) |
C13—C14 | 1.363 (9) | C56—H56 | 0.9500 |
C13—C17 | 1.413 (8) | C56—C57 | 1.376 (10) |
C14—H14 | 0.9500 | C57—H57 | 0.9500 |
C14—C15 | 1.356 (9) | C57—C58 | 1.380 (9) |
C15—H15 | 0.9500 | C58—H58 | 0.9500 |
C16—H16 | 0.9500 | C59—C60 | 1.405 (7) |
C16—C17 | 1.366 (9) | C59—C62 | 1.383 (8) |
C17—H17 | 0.9500 | C60—H60 | 0.9500 |
C18—C19 | 1.495 (7) | C60—C61 | 1.368 (7) |
C18—C25 | 1.485 (7) | C61—C64 | 1.451 (8) |
C19—C20 | 1.387 (7) | C62—C63 | 1.494 (8) |
C19—C24 | 1.391 (7) | C63—H63A | 0.9800 |
C20—H20 | 0.9500 | C63—H63B | 0.9800 |
C20—C21 | 1.396 (7) | C63—H63C | 0.9800 |
C21—H21 | 0.9500 | C64—C65 | 1.395 (8) |
C21—C22 | 1.383 (8) | C64—C68 | 1.407 (7) |
C22—H22 | 0.9500 | C65—H65 | 0.9500 |
C22—C23 | 1.386 (7) | C65—C66 | 1.355 (8) |
C23—H23 | 0.9500 | C66—H66 | 0.9500 |
C23—C24 | 1.392 (7) | C67—H67 | 0.9500 |
C24—H24 | 0.9500 | C67—C68 | 1.380 (8) |
C25—C26 | 1.411 (7) | C68—H68 | 0.9500 |
C25—C28 | 1.374 (7) | O1—C69 | 1.270 (6) |
C26—H26 | 0.9500 | O2—C69 | 1.260 (7) |
C26—C27 | 1.370 (7) | O3—C71 | 1.351 (7) |
C27—C30 | 1.450 (7) | O3—H3C | 0.84 (2) |
C28—C29 | 1.493 (7) | O4—C75 | 1.344 (9) |
C29—H29A | 0.9800 | O4—H4C | 0.84 (2) |
C29—H29B | 0.9800 | C69—C70 | 1.480 (8) |
C29—H29C | 0.9800 | C70—C71 | 1.407 (9) |
C30—C31 | 1.415 (7) | C70—C75 | 1.408 (8) |
C30—C34 | 1.399 (7) | C71—C72 | 1.379 (8) |
C31—H31 | 0.9500 | C72—H72 | 0.9500 |
C31—C32 | 1.354 (7) | C72—C73 | 1.375 (12) |
C32—H32 | 0.9500 | C73—H73 | 0.9500 |
C33—H33 | 0.9500 | C73—C74 | 1.347 (12) |
C33—C34 | 1.363 (7) | C74—H74 | 0.9500 |
C34—H34 | 0.9500 | C74—C75 | 1.387 (10) |
C2—C3 | 1.45 (3) | O5—C76 | 1.284 (6) |
C2—C7 | 1.38 (2) | O6—C76 | 1.258 (6) |
C3—H3 | 0.9500 | O7—C78 | 1.371 (6) |
C3—C4 | 1.35 (2) | O7—H7B | 0.85 (2) |
C4—H4 | 0.9500 | O8—C82 | 1.355 (6) |
C4—C6 | 1.39 (2) | O8—H8 | 0.84 (2) |
C5—H5 | 0.9500 | C76—C77 | 1.477 (7) |
C5—C6 | 1.37 (2) | C77—C78 | 1.407 (7) |
C5—C7 | 1.40 (2) | C77—C82 | 1.414 (7) |
C6—H6 | 0.9500 | C78—C79 | 1.386 (7) |
C7—H7 | 0.9500 | C79—H79 | 0.9500 |
C2A—C3A | 1.33 (5) | C79—C80 | 1.399 (7) |
C2A—C7A | 1.41 (4) | C80—H80 | 0.9500 |
C3A—H3A | 0.9500 | C80—C81 | 1.380 (8) |
C3A—C4A | 1.41 (4) | C81—H81 | 0.9500 |
C4A—H4A | 0.9500 | C81—C82 | 1.389 (7) |
C4A—C5A | 1.42 (4) | O9—C83 | 1.300 (7) |
C5A—H5A | 0.9500 | O10—C83 | 1.254 (7) |
C5A—C6A | 1.39 (4) | O11—C85 | 1.361 (6) |
C6A—H6A | 0.9500 | O11—H11 | 0.85 (2) |
C6A—C7A | 1.37 (3) | O12—C89 | 1.351 (6) |
C7A—H7A | 0.9500 | O12—H12 | 0.85 (2) |
S3—C44 | 1.732 (5) | C83—C84 | 1.463 (8) |
S3—C45 | 1.720 (5) | C84—C85 | 1.402 (7) |
S4—C61 | 1.726 (5) | C84—C89 | 1.424 (7) |
S4—C62 | 1.727 (6) | C85—C86 | 1.383 (8) |
N3—C49 | 1.332 (6) | C86—H86 | 0.9500 |
N3—C50 | 1.343 (7) | C86—C87 | 1.388 (7) |
N3—H3B | 0.88 (2) | C87—H87 | 0.9500 |
N4—C66 | 1.348 (7) | C87—C88 | 1.372 (8) |
N4—C67 | 1.330 (7) | C88—H88 | 0.9500 |
N4—H4B | 0.90 (2) | C88—C89 | 1.375 (8) |
C35—C36 | 1.496 (8) | O13—C90 | 1.299 (14) |
C35—C42 | 1.505 (7) | O14—C90 | 1.260 (14) |
C35—C52 | 1.351 (7) | O15—H15A | 0.84 (2) |
C36—C37 | 1.382 (8) | O15—C92 | 1.366 (15) |
C36—C41 | 1.404 (8) | O16—H16A | 0.84 (2) |
C37—H37 | 0.9500 | O16—C96 | 1.345 (17) |
C37—C38 | 1.373 (8) | C90—C91 | 1.445 (12) |
C38—H38 | 0.9500 | C91—C92 | 1.403 (15) |
C38—C39 | 1.366 (9) | C91—C96 | 1.420 (15) |
C39—H39 | 0.9500 | C92—C93 | 1.418 (16) |
C39—C40 | 1.357 (11) | C93—H93 | 0.9500 |
C40—H40 | 0.9500 | C93—C94 | 1.377 (14) |
C40—C41 | 1.386 (10) | C94—H94 | 0.9500 |
C41—H41 | 0.9500 | C94—C95 | 1.370 (14) |
C42—C43 | 1.407 (7) | C95—H95 | 0.9500 |
C42—C45 | 1.375 (7) | C95—C96 | 1.389 (18) |
C11—S1—C10 | 92.6 (3) | C43—C44—C47 | 129.8 (4) |
C28—S2—C27 | 92.4 (2) | C47—C44—S3 | 120.1 (3) |
C15—N1—H1 | 115 (10) | C42—C45—S3 | 111.5 (4) |
C16—N1—C15 | 118.0 (6) | C42—C45—C46 | 129.0 (5) |
C16—N1—H1 | 126 (10) | C46—C45—S3 | 119.5 (4) |
C32—N2—C33 | 120.4 (4) | C45—C46—H46A | 109.5 |
C32—N2—H2 | 122 (5) | C45—C46—H46B | 109.5 |
C33—N2—H2 | 118 (5) | C45—C46—H46C | 109.5 |
C8—C1—C2A | 121 (2) | H46A—C46—H46B | 109.5 |
C18—C1—C8 | 120.9 (5) | H46A—C46—H46C | 109.5 |
C18—C1—C2 | 127.6 (14) | H46B—C46—H46C | 109.5 |
C18—C1—C2A | 117 (2) | C48—C47—C44 | 121.9 (4) |
C2—C1—C8 | 111.5 (13) | C51—C47—C44 | 121.9 (4) |
C9—C8—C1 | 122.7 (5) | C51—C47—C48 | 116.2 (5) |
C11—C8—C1 | 124.4 (5) | C47—C48—H48 | 119.6 |
C11—C8—C9 | 112.9 (5) | C49—C48—C47 | 120.8 (5) |
C8—C9—H9 | 123.2 | C49—C48—H48 | 119.6 |
C10—C9—C8 | 113.5 (5) | N3—C49—C48 | 121.1 (5) |
C10—C9—H9 | 123.2 | N3—C49—H49 | 119.5 |
C9—C10—S1 | 109.7 (4) | C48—C49—H49 | 119.5 |
C9—C10—C13 | 127.1 (6) | N3—C50—H50 | 120.2 |
C13—C10—S1 | 123.2 (4) | N3—C50—C51 | 119.7 (5) |
C8—C11—S1 | 111.3 (4) | C51—C50—H50 | 120.2 |
C8—C11—C12 | 129.2 (5) | C47—C51—H51 | 119.4 |
C12—C11—S1 | 119.5 (4) | C50—C51—C47 | 121.1 (5) |
C11—C12—H12A | 109.5 | C50—C51—H51 | 119.4 |
C11—C12—H12B | 109.5 | C35—C52—C53 | 124.8 (5) |
C11—C12—H12C | 109.5 | C35—C52—C59 | 119.0 (5) |
H12A—C12—H12B | 109.5 | C53—C52—C59 | 116.2 (5) |
H12A—C12—H12C | 109.5 | C54—C53—C52 | 120.5 (5) |
H12B—C12—H12C | 109.5 | C58—C53—C52 | 121.1 (5) |
C14—C13—C10 | 122.5 (6) | C58—C53—C54 | 118.3 (5) |
C14—C13—C17 | 116.4 (6) | C53—C54—H54 | 119.4 |
C17—C13—C10 | 121.1 (6) | C55—C54—C53 | 121.3 (6) |
C13—C14—H14 | 118.8 | C55—C54—H54 | 119.4 |
C15—C14—C13 | 122.5 (7) | C54—C55—H55 | 120.2 |
C15—C14—H14 | 118.8 | C56—C55—C54 | 119.5 (6) |
N1—C15—C14 | 120.8 (8) | C56—C55—H55 | 120.2 |
N1—C15—H15 | 119.6 | C55—C56—H56 | 120.2 |
C14—C15—H15 | 119.6 | C57—C56—C55 | 119.6 (6) |
N1—C16—H16 | 117.8 | C57—C56—H56 | 120.2 |
N1—C16—C17 | 124.3 (7) | C56—C57—H57 | 119.8 |
C17—C16—H16 | 117.8 | C56—C57—C58 | 120.4 (7) |
C13—C17—H17 | 121.0 | C58—C57—H57 | 119.8 |
C16—C17—C13 | 118.0 (7) | C53—C58—C57 | 120.9 (6) |
C16—C17—H17 | 121.0 | C53—C58—H58 | 119.5 |
C1—C18—C19 | 123.4 (5) | C57—C58—H58 | 119.5 |
C1—C18—C25 | 121.2 (5) | C60—C59—C52 | 121.7 (5) |
C25—C18—C19 | 115.4 (4) | C62—C59—C52 | 127.1 (5) |
C20—C19—C18 | 119.7 (5) | C62—C59—C60 | 111.2 (5) |
C20—C19—C24 | 119.7 (5) | C59—C60—H60 | 122.4 |
C24—C19—C18 | 120.6 (4) | C61—C60—C59 | 115.3 (5) |
C19—C20—H20 | 119.7 | C61—C60—H60 | 122.4 |
C19—C20—C21 | 120.6 (5) | C60—C61—S4 | 109.8 (4) |
C21—C20—H20 | 119.7 | C60—C61—C64 | 126.5 (5) |
C20—C21—H21 | 120.3 | C64—C61—S4 | 123.7 (4) |
C22—C21—C20 | 119.4 (5) | C59—C62—S4 | 111.3 (4) |
C22—C21—H21 | 120.3 | C59—C62—C63 | 129.5 (6) |
C21—C22—H22 | 119.9 | C63—C62—S4 | 119.2 (5) |
C21—C22—C23 | 120.1 (5) | C62—C63—H63A | 109.5 |
C23—C22—H22 | 119.9 | C62—C63—H63B | 109.5 |
C22—C23—H23 | 119.8 | C62—C63—H63C | 109.5 |
C22—C23—C24 | 120.5 (5) | H63A—C63—H63B | 109.5 |
C24—C23—H23 | 119.8 | H63A—C63—H63C | 109.5 |
C19—C24—C23 | 119.6 (5) | H63B—C63—H63C | 109.5 |
C19—C24—H24 | 120.2 | C65—C64—C61 | 120.6 (5) |
C23—C24—H24 | 120.2 | C65—C64—C68 | 116.4 (5) |
C26—C25—C18 | 124.5 (4) | C68—C64—C61 | 123.0 (5) |
C28—C25—C18 | 122.9 (5) | C64—C65—H65 | 119.4 |
C28—C25—C26 | 112.5 (4) | C66—C65—C64 | 121.3 (5) |
C25—C26—H26 | 123.1 | C66—C65—H65 | 119.4 |
C27—C26—C25 | 113.8 (4) | N4—C66—C65 | 120.5 (5) |
C27—C26—H26 | 123.1 | N4—C66—H66 | 119.7 |
C26—C27—S2 | 110.1 (4) | C65—C66—H66 | 119.7 |
C26—C27—C30 | 129.5 (5) | N4—C67—H67 | 119.8 |
C30—C27—S2 | 120.4 (4) | N4—C67—C68 | 120.5 (5) |
C25—C28—S2 | 111.1 (4) | C68—C67—H67 | 119.8 |
C25—C28—C29 | 129.2 (5) | C64—C68—H68 | 119.9 |
C29—C28—S2 | 119.7 (4) | C67—C68—C64 | 120.2 (5) |
C28—C29—H29A | 109.5 | C67—C68—H68 | 119.9 |
C28—C29—H29B | 109.5 | C71—O3—H3C | 112 (5) |
C28—C29—H29C | 109.5 | C75—O4—H4C | 118 (6) |
H29A—C29—H29B | 109.5 | O1—C69—C70 | 118.1 (5) |
H29A—C29—H29C | 109.5 | O2—C69—O1 | 122.6 (5) |
H29B—C29—H29C | 109.5 | O2—C69—C70 | 119.4 (5) |
C31—C30—C27 | 121.6 (4) | C71—C70—C69 | 122.2 (5) |
C34—C30—C27 | 121.5 (4) | C71—C70—C75 | 117.3 (6) |
C34—C30—C31 | 116.9 (4) | C75—C70—C69 | 120.5 (6) |
C30—C31—H31 | 120.2 | O3—C71—C70 | 121.0 (5) |
C32—C31—C30 | 119.6 (5) | O3—C71—C72 | 117.6 (6) |
C32—C31—H31 | 120.2 | C72—C71—C70 | 121.4 (6) |
N2—C32—C31 | 121.9 (5) | C71—C72—H72 | 120.6 |
N2—C32—H32 | 119.0 | C73—C72—C71 | 118.8 (8) |
C31—C32—H32 | 119.0 | C73—C72—H72 | 120.6 |
N2—C33—H33 | 119.9 | C72—C73—H73 | 119.1 |
N2—C33—C34 | 120.3 (5) | C74—C73—C72 | 121.9 (7) |
C34—C33—H33 | 119.9 | C74—C73—H73 | 119.1 |
C30—C34—H34 | 119.5 | C73—C74—H74 | 119.9 |
C33—C34—C30 | 120.9 (5) | C73—C74—C75 | 120.3 (7) |
C33—C34—H34 | 119.5 | C75—C74—H74 | 119.9 |
C3—C2—C1 | 122.3 (16) | O4—C75—C70 | 120.7 (6) |
C7—C2—C1 | 122 (2) | O4—C75—C74 | 119.0 (7) |
C7—C2—C3 | 115 (2) | C74—C75—C70 | 120.3 (8) |
C2—C3—H3 | 119.0 | C78—O7—H7B | 102 (5) |
C4—C3—C2 | 122.0 (17) | C82—O8—H8 | 100 (5) |
C4—C3—H3 | 119.0 | O5—C76—C77 | 118.8 (5) |
C3—C4—H4 | 119.9 | O6—C76—O5 | 123.0 (5) |
C3—C4—C6 | 120.2 (14) | O6—C76—C77 | 118.1 (5) |
C6—C4—H4 | 119.9 | C78—C77—C76 | 121.7 (4) |
C6—C5—H5 | 120.2 | C78—C77—C82 | 117.5 (5) |
C6—C5—C7 | 119.6 (16) | C82—C77—C76 | 120.8 (5) |
C7—C5—H5 | 120.2 | O7—C78—C77 | 120.4 (4) |
C4—C6—H6 | 119.8 | O7—C78—C79 | 117.4 (4) |
C5—C6—C4 | 120.5 (16) | C79—C78—C77 | 122.2 (5) |
C5—C6—H6 | 119.8 | C78—C79—H79 | 121.0 |
C2—C7—C5 | 122.4 (17) | C78—C79—C80 | 118.0 (5) |
C2—C7—H7 | 118.8 | C80—C79—H79 | 121.0 |
C5—C7—H7 | 118.8 | C79—C80—H80 | 119.1 |
C3A—C2A—C1 | 116 (3) | C81—C80—C79 | 121.8 (5) |
C3A—C2A—C7A | 125 (4) | C81—C80—H80 | 119.1 |
C7A—C2A—C1 | 117 (4) | C80—C81—H81 | 120.3 |
C2A—C3A—H3A | 121.1 | C80—C81—C82 | 119.5 (5) |
C2A—C3A—C4A | 118 (3) | C82—C81—H81 | 120.3 |
C4A—C3A—H3A | 121.1 | O8—C82—C77 | 121.0 (5) |
C3A—C4A—H4A | 120.4 | O8—C82—C81 | 118.1 (5) |
C3A—C4A—C5A | 119 (3) | C81—C82—C77 | 120.9 (5) |
C5A—C4A—H4A | 120.4 | C85—O11—H11 | 110 (5) |
C4A—C5A—H5A | 120.6 | C89—O12—H12 | 109 (5) |
C6A—C5A—C4A | 119 (2) | O9—C83—C84 | 117.0 (5) |
C6A—C5A—H5A | 120.6 | O10—C83—O9 | 121.9 (5) |
C5A—C6A—H6A | 119.1 | O10—C83—C84 | 121.1 (5) |
C7A—C6A—C5A | 122 (2) | C85—C84—C83 | 122.4 (5) |
C7A—C6A—H6A | 119.1 | C85—C84—C89 | 117.4 (5) |
C2A—C7A—H7A | 121.8 | C89—C84—C83 | 120.3 (5) |
C6A—C7A—C2A | 116 (3) | O11—C85—C84 | 120.7 (5) |
C6A—C7A—H7A | 121.8 | O11—C85—C86 | 118.1 (5) |
C45—S3—C44 | 92.2 (2) | C86—C85—C84 | 121.2 (5) |
C61—S4—C62 | 92.3 (3) | C85—C86—H86 | 120.2 |
C49—N3—C50 | 121.1 (4) | C85—C86—C87 | 119.6 (5) |
C49—N3—H3B | 124 (5) | C87—C86—H86 | 120.2 |
C50—N3—H3B | 114 (5) | C86—C87—H87 | 119.6 |
C66—N4—H4B | 121 (5) | C88—C87—C86 | 120.9 (5) |
C67—N4—C66 | 121.1 (5) | C88—C87—H87 | 119.6 |
C67—N4—H4B | 118 (5) | C87—C88—H88 | 120.0 |
C36—C35—C42 | 115.4 (4) | C87—C88—C89 | 120.1 (5) |
C52—C35—C36 | 126.2 (5) | C89—C88—H88 | 120.0 |
C52—C35—C42 | 118.4 (5) | O12—C89—C84 | 120.3 (5) |
C37—C36—C35 | 120.0 (5) | O12—C89—C88 | 118.8 (5) |
C37—C36—C41 | 116.5 (6) | C88—C89—C84 | 120.9 (5) |
C41—C36—C35 | 123.2 (5) | C92—O15—H15A | 111 (10) |
C36—C37—H37 | 119.0 | C96—O16—H16A | 99 (10) |
C38—C37—C36 | 121.9 (6) | O13—C90—C91 | 117.8 (12) |
C38—C37—H37 | 119.0 | O14—C90—O13 | 119.1 (16) |
C37—C38—H38 | 119.6 | O14—C90—C91 | 123.1 (13) |
C39—C38—C37 | 120.9 (7) | C92—C91—C90 | 122.0 (13) |
C39—C38—H38 | 119.6 | C92—C91—C96 | 118.7 (15) |
C38—C39—H39 | 120.6 | C96—C91—C90 | 119.2 (12) |
C40—C39—C38 | 118.8 (7) | O15—C92—C91 | 121.1 (15) |
C40—C39—H39 | 120.6 | O15—C92—C93 | 117.1 (14) |
C39—C40—H40 | 119.4 | C91—C92—C93 | 121.4 (13) |
C39—C40—C41 | 121.3 (7) | C92—C93—H93 | 121.5 |
C41—C40—H40 | 119.4 | C94—C93—C92 | 116.9 (12) |
C36—C41—H41 | 119.7 | C94—C93—H93 | 121.5 |
C40—C41—C36 | 120.6 (7) | C93—C94—H94 | 118.4 |
C40—C41—H41 | 119.7 | C95—C94—C93 | 123.2 (14) |
C43—C42—C35 | 125.4 (4) | C95—C94—H94 | 118.4 |
C45—C42—C35 | 122.3 (4) | C94—C95—H95 | 119.8 |
C45—C42—C43 | 112.2 (4) | C94—C95—C96 | 120.4 (14) |
C42—C43—H43 | 123.0 | C96—C95—H95 | 119.8 |
C44—C43—C42 | 114.1 (4) | O16—C96—C91 | 118.7 (16) |
C44—C43—H43 | 123.0 | O16—C96—C95 | 121.8 (18) |
C43—C44—S3 | 110.0 (3) | C95—C96—C91 | 119.2 (15) |
S1—C10—C13—C14 | 176.2 (5) | C42—C35—C52—C59 | −13.4 (7) |
S1—C10—C13—C17 | −5.0 (7) | C42—C43—C44—S3 | 0.2 (6) |
S2—C27—C30—C31 | 163.6 (4) | C42—C43—C44—C47 | −175.8 (5) |
S2—C27—C30—C34 | −16.5 (6) | C43—C42—C45—S3 | −0.9 (6) |
N1—C16—C17—C13 | 2.0 (9) | C43—C42—C45—C46 | −179.2 (5) |
N2—C33—C34—C30 | 1.2 (7) | C43—C44—C47—C48 | 1.0 (9) |
C1—C8—C9—C10 | −178.2 (5) | C43—C44—C47—C51 | 179.5 (6) |
C1—C8—C11—S1 | 178.3 (4) | C44—S3—C45—C42 | 0.8 (4) |
C1—C8—C11—C12 | −0.1 (9) | C44—S3—C45—C46 | 179.3 (5) |
C1—C18—C19—C20 | −133.6 (6) | C44—C47—C48—C49 | 179.0 (5) |
C1—C18—C19—C24 | 46.7 (7) | C44—C47—C51—C50 | −178.9 (6) |
C1—C18—C25—C26 | −115.3 (6) | C45—S3—C44—C43 | −0.6 (4) |
C1—C18—C25—C28 | 63.1 (7) | C45—S3—C44—C47 | 175.9 (4) |
C1—C2—C3—C4 | −179 (3) | C45—C42—C43—C44 | 0.5 (7) |
C1—C2—C7—C5 | 179 (2) | C47—C48—C49—N3 | −0.9 (9) |
C1—C2A—C3A—C4A | −174 (4) | C48—C47—C51—C50 | −0.4 (9) |
C1—C2A—C7A—C6A | 170 (4) | C49—N3—C50—C51 | −1.1 (10) |
C8—C1—C18—C19 | −173.2 (5) | C50—N3—C49—C48 | 1.2 (9) |
C8—C1—C18—C25 | 8.4 (8) | C51—C47—C48—C49 | 0.5 (8) |
C8—C1—C2—C3 | 49 (3) | C52—C35—C36—C37 | 165.0 (5) |
C8—C1—C2—C7 | −134 (3) | C52—C35—C36—C41 | −22.3 (8) |
C8—C1—C2A—C3A | 48 (6) | C52—C35—C42—C43 | 113.1 (6) |
C8—C1—C2A—C7A | −118 (4) | C52—C35—C42—C45 | −65.0 (7) |
C8—C9—C10—S1 | −0.7 (6) | C52—C53—C54—C55 | −179.7 (7) |
C8—C9—C10—C13 | 177.7 (5) | C52—C53—C58—C57 | −178.1 (8) |
C9—C8—C11—S1 | −1.2 (6) | C52—C59—C60—C61 | 175.7 (4) |
C9—C8—C11—C12 | −179.6 (5) | C52—C59—C62—S4 | −175.9 (4) |
C9—C10—C13—C14 | −2.1 (9) | C52—C59—C62—C63 | 4.1 (9) |
C9—C10—C13—C17 | 176.8 (5) | C53—C52—C59—C60 | 130.7 (5) |
C10—S1—C11—C8 | 0.7 (4) | C53—C52—C59—C62 | −50.9 (7) |
C10—S1—C11—C12 | 179.2 (5) | C53—C54—C55—C56 | −3.6 (12) |
C10—C13—C14—C15 | −179.2 (6) | C54—C53—C58—C57 | −0.9 (12) |
C10—C13—C17—C16 | 178.5 (5) | C54—C55—C56—C57 | 1.7 (14) |
C11—S1—C10—C9 | 0.1 (4) | C55—C56—C57—C58 | 0.4 (16) |
C11—S1—C10—C13 | −178.4 (5) | C56—C57—C58—C53 | −0.9 (15) |
C11—C8—C9—C10 | 1.3 (6) | C58—C53—C54—C55 | 3.1 (11) |
C13—C14—C15—N1 | −0.5 (11) | C59—C52—C53—C54 | −55.0 (8) |
C14—C13—C17—C16 | −2.6 (8) | C59—C52—C53—C58 | 122.1 (7) |
C15—N1—C16—C17 | −0.4 (10) | C59—C60—C61—S4 | 1.9 (6) |
C16—N1—C15—C14 | −0.4 (10) | C59—C60—C61—C64 | −177.2 (5) |
C17—C13—C14—C15 | 2.0 (10) | C60—C59—C62—S4 | 2.6 (5) |
C18—C1—C8—C9 | 50.2 (7) | C60—C59—C62—C63 | −177.4 (5) |
C18—C1—C8—C11 | −129.2 (6) | C60—C61—C64—C65 | −3.8 (8) |
C18—C1—C2—C3 | −129 (2) | C60—C61—C64—C68 | 174.3 (5) |
C18—C1—C2—C7 | 48 (4) | C61—S4—C62—C59 | −1.4 (4) |
C18—C1—C2A—C3A | −138 (4) | C61—S4—C62—C63 | 178.6 (5) |
C18—C1—C2A—C7A | 56 (6) | C61—C64—C65—C66 | 176.9 (5) |
C18—C19—C20—C21 | 178.9 (5) | C61—C64—C68—C67 | −177.1 (5) |
C18—C19—C24—C23 | −179.7 (4) | C62—S4—C61—C60 | −0.2 (4) |
C18—C25—C26—C27 | 175.9 (4) | C62—S4—C61—C64 | 178.9 (4) |
C18—C25—C28—S2 | −177.0 (4) | C62—C59—C60—C61 | −3.0 (6) |
C18—C25—C28—C29 | 3.4 (8) | C64—C65—C66—N4 | 0.6 (9) |
C19—C18—C25—C26 | 66.2 (6) | C65—C64—C68—C67 | 1.1 (7) |
C19—C18—C25—C28 | −115.4 (5) | C66—N4—C67—C68 | −0.9 (8) |
C19—C20—C21—C22 | 1.6 (8) | C67—N4—C66—C65 | 0.5 (9) |
C20—C19—C24—C23 | 0.6 (7) | C68—C64—C65—C66 | −1.4 (8) |
C20—C21—C22—C23 | −1.1 (8) | O1—C69—C70—C71 | −1.6 (7) |
C21—C22—C23—C24 | 0.3 (8) | O1—C69—C70—C75 | 177.6 (5) |
C22—C23—C24—C19 | 0.0 (8) | O2—C69—C70—C71 | 177.9 (5) |
C24—C19—C20—C21 | −1.4 (8) | O2—C69—C70—C75 | −2.9 (7) |
C25—C18—C19—C20 | 45.0 (6) | O3—C71—C72—C73 | 178.9 (5) |
C25—C18—C19—C24 | −134.7 (5) | C69—C70—C71—O3 | 1.4 (7) |
C25—C26—C27—S2 | 2.4 (5) | C69—C70—C71—C72 | −177.8 (5) |
C25—C26—C27—C30 | −175.3 (5) | C69—C70—C75—O4 | −1.6 (8) |
C26—C25—C28—S2 | 1.5 (5) | C69—C70—C75—C74 | 178.4 (5) |
C26—C25—C28—C29 | −178.0 (5) | C70—C71—C72—C73 | −2.0 (8) |
C26—C27—C30—C31 | −18.9 (8) | C71—C70—C75—O4 | 177.6 (5) |
C26—C27—C30—C34 | 160.9 (5) | C71—C70—C75—C74 | −2.4 (8) |
C27—S2—C28—C25 | −0.2 (4) | C71—C72—C73—C74 | 0.1 (9) |
C27—S2—C28—C29 | 179.4 (4) | C72—C73—C74—C75 | 0.5 (10) |
C27—C30—C31—C32 | 178.4 (4) | C73—C74—C75—O4 | −179.3 (6) |
C27—C30—C34—C33 | −179.6 (4) | C73—C74—C75—C70 | 0.7 (10) |
C28—S2—C27—C26 | −1.3 (4) | C75—C70—C71—O3 | −177.8 (5) |
C28—S2—C27—C30 | 176.7 (4) | C75—C70—C71—C72 | 3.1 (8) |
C28—C25—C26—C27 | −2.6 (6) | O5—C76—C77—C78 | 9.4 (8) |
C30—C31—C32—N2 | 1.4 (7) | O5—C76—C77—C82 | −172.2 (5) |
C31—C30—C34—C33 | 0.3 (7) | O6—C76—C77—C78 | −169.8 (5) |
C32—N2—C33—C34 | −1.4 (7) | O6—C76—C77—C82 | 8.6 (8) |
C33—N2—C32—C31 | 0.1 (7) | O7—C78—C79—C80 | −177.8 (4) |
C34—C30—C31—C32 | −1.5 (7) | C76—C77—C78—O7 | −3.0 (8) |
C2—C1—C8—C9 | −128.4 (15) | C76—C77—C78—C79 | 176.5 (5) |
C2—C1—C8—C11 | 52.2 (16) | C76—C77—C82—O8 | 2.4 (8) |
C2—C1—C18—C19 | 5.2 (19) | C76—C77—C82—C81 | −177.7 (5) |
C2—C1—C18—C25 | −173.3 (17) | C77—C78—C79—C80 | 2.6 (8) |
C2—C3—C4—C6 | −2 (3) | C78—C77—C82—O8 | −179.1 (5) |
C3—C2—C7—C5 | −4 (4) | C78—C77—C82—C81 | 0.8 (8) |
C3—C4—C6—C5 | 0 (3) | C78—C79—C80—C81 | −2.2 (8) |
C6—C5—C7—C2 | 2 (3) | C79—C80—C81—C82 | 1.2 (8) |
C7—C2—C3—C4 | 4 (4) | C80—C81—C82—O8 | 179.5 (5) |
C7—C5—C6—C4 | 0 (3) | C80—C81—C82—C77 | −0.5 (8) |
C2A—C1—C8—C9 | −136 (3) | C82—C77—C78—O7 | 178.5 (4) |
C2A—C1—C8—C11 | 45 (3) | C82—C77—C78—C79 | −2.0 (8) |
C2A—C1—C18—C19 | 13 (3) | O9—C83—C84—C85 | −2.5 (8) |
C2A—C1—C18—C25 | −166 (3) | O9—C83—C84—C89 | 177.9 (5) |
C2A—C3A—C4A—C5A | 3 (6) | O10—C83—C84—C85 | 177.5 (5) |
C3A—C2A—C7A—C6A | 6 (8) | O10—C83—C84—C89 | −2.2 (8) |
C3A—C4A—C5A—C6A | 6 (5) | O11—C85—C86—C87 | −179.9 (5) |
C4A—C5A—C6A—C7A | −11 (4) | C83—C84—C85—O11 | 0.7 (8) |
C5A—C6A—C7A—C2A | 5 (5) | C83—C84—C85—C86 | −178.6 (5) |
C7A—C2A—C3A—C4A | −9 (8) | C83—C84—C89—O12 | −0.6 (7) |
S3—C44—C47—C48 | −174.6 (4) | C83—C84—C89—C88 | 179.1 (5) |
S3—C44—C47—C51 | 3.9 (7) | C84—C85—C86—C87 | −0.6 (8) |
S4—C61—C64—C65 | 177.2 (4) | C85—C84—C89—O12 | 179.7 (5) |
S4—C61—C64—C68 | −4.7 (7) | C85—C84—C89—C88 | −0.6 (7) |
N3—C50—C51—C47 | 0.7 (11) | C85—C86—C87—C88 | −0.3 (8) |
N4—C67—C68—C64 | 0.0 (8) | C86—C87—C88—C89 | 0.7 (8) |
C35—C36—C37—C38 | 172.4 (5) | C87—C88—C89—O12 | 179.4 (5) |
C35—C36—C41—C40 | −173.2 (6) | C87—C88—C89—C84 | −0.3 (8) |
C35—C42—C43—C44 | −177.8 (5) | C89—C84—C85—O11 | −179.7 (5) |
C35—C42—C45—S3 | 177.4 (4) | C89—C84—C85—C86 | 1.0 (8) |
C35—C42—C45—C46 | −0.8 (9) | O13—C90—C91—C92 | 1.3 (16) |
C35—C52—C53—C54 | 123.8 (7) | O13—C90—C91—C96 | −178.5 (16) |
C35—C52—C53—C58 | −59.1 (9) | O14—C90—C91—C92 | −178.4 (16) |
C35—C52—C59—C60 | −48.2 (7) | O14—C90—C91—C96 | 1.8 (17) |
C35—C52—C59—C62 | 130.2 (6) | O15—C92—C93—C94 | −177.1 (12) |
C36—C35—C42—C43 | −66.3 (7) | C90—C91—C92—O15 | −4 (2) |
C36—C35—C42—C45 | 115.6 (6) | C90—C91—C92—C93 | −176.3 (13) |
C36—C35—C52—C53 | −12.9 (8) | C90—C91—C96—O16 | −6 (2) |
C36—C35—C52—C59 | 165.9 (5) | C90—C91—C96—C95 | 179.7 (13) |
C36—C37—C38—C39 | 1.1 (10) | C91—C92—C93—C94 | −4 (2) |
C37—C36—C41—C40 | −0.2 (9) | C92—C91—C96—O16 | 174.2 (14) |
C37—C38—C39—C40 | −0.2 (10) | C92—C91—C96—C95 | 0 (2) |
C38—C39—C40—C41 | −0.8 (11) | C92—C93—C94—C95 | 1 (2) |
C39—C40—C41—C36 | 1.0 (11) | C93—C94—C95—C96 | 2 (2) |
C41—C36—C37—C38 | −0.8 (9) | C94—C95—C96—O16 | −176.7 (14) |
C42—C35—C36—C37 | −15.8 (7) | C94—C95—C96—C91 | −3 (2) |
C42—C35—C36—C41 | 157.0 (5) | C96—C91—C92—O15 | 176.1 (14) |
C42—C35—C52—C53 | 167.8 (5) | C96—C91—C92—C93 | 3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15A···O13 | 0.84 (2) | 1.86 (11) | 2.516 (18) | 133 (13) |
O16—H16A···O14 | 0.84 (2) | 1.68 (5) | 2.499 (19) | 162 (14) |
N1—H1···N1i | 0.88 (2) | 1.76 (3) | 2.641 (11) | 174 (19) |
N2—H2···O1i | 0.89 (2) | 1.79 (2) | 2.669 (5) | 172 (7) |
N3—H3B···O5i | 0.88 (2) | 1.88 (2) | 2.766 (5) | 175 (7) |
N4—H4B···O9ii | 0.90 (2) | 1.71 (3) | 2.602 (6) | 170 (8) |
O3—H3C···O1 | 0.84 (2) | 1.84 (5) | 2.561 (5) | 142 (7) |
O4—H4C···O2 | 0.84 (2) | 1.86 (6) | 2.524 (6) | 135 (8) |
O7—H7B···O5 | 0.85 (2) | 1.75 (3) | 2.553 (5) | 158 (8) |
O8—H8···O6 | 0.84 (2) | 1.72 (3) | 2.531 (5) | 160 (8) |
O11—H11···O9 | 0.85 (2) | 1.77 (5) | 2.515 (6) | 146 (8) |
O12—H12···O10 | 0.85 (2) | 1.77 (4) | 2.544 (6) | 149 (8) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |
C34H28N2S2·C10H5O8·C5H2O4 | F(000) = 1884 |
Mr = 907.91 | Dx = 1.336 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6987 (2) Å | Cell parameters from 6590 reflections |
b = 20.7245 (5) Å | θ = 2.4–23.8° |
c = 22.9341 (6) Å | µ = 0.18 mm−1 |
β = 101.680 (1)° | T = 90 K |
V = 4514.32 (19) Å3 | Prism, green |
Z = 4 | 0.12 × 0.06 × 0.04 mm |
Bruker APEX-II CCD diffractometer | 6215 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.079 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1841 before and 0.0535 after correction. The Ratio of minimum to maximum transmission is 0.9548. The λ/2 correction factor is Not present. | θmax = 26.4°, θmin = 1.3° |
Tmin = 0.712, Tmax = 0.745 | h = −10→12 |
57175 measured reflections | k = −25→25 |
9238 independent reflections | l = −28→28 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0438P)2 + 2.8563P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
9238 reflections | Δρmax = 0.46 e Å−3 |
631 parameters | Δρmin = −0.40 e Å−3 |
5 restraints |
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) | |
S1 | −0.14749 (8) | 0.28773 (3) | 0.28157 (3) | 0.03515 (19) | |
S2 | 0.40518 (9) | 0.32119 (3) | 0.27207 (3) | 0.03811 (19) | |
N1 | 0.1231 (2) | 0.13683 (10) | 0.45741 (10) | 0.0223 (5) | |
N2 | 0.8210 (2) | 0.28595 (11) | 0.46054 (11) | 0.0347 (6) | |
C1 | 0.0398 (3) | 0.46154 (13) | 0.29057 (11) | 0.0294 (6) | |
C2 | −0.0724 (3) | 0.51135 (14) | 0.27680 (12) | 0.0338 (7) | |
C3 | −0.1743 (3) | 0.51771 (17) | 0.31114 (15) | 0.0539 (10) | |
H3 | −0.168259 | 0.492108 | 0.345924 | 0.065* | |
C4 | −0.2845 (4) | 0.5609 (2) | 0.29533 (19) | 0.0824 (15) | |
H4 | −0.353996 | 0.564962 | 0.318961 | 0.099* | |
C5 | −0.2921 (4) | 0.5982 (2) | 0.24460 (18) | 0.0771 (14) | |
H5 | −0.367989 | 0.627548 | 0.233184 | 0.093* | |
C6 | −0.1912 (3) | 0.59310 (16) | 0.21069 (15) | 0.0487 (9) | |
H6 | −0.197097 | 0.619075 | 0.176146 | 0.058* | |
C7 | −0.0810 (3) | 0.55025 (13) | 0.22674 (12) | 0.0339 (7) | |
H7 | −0.010575 | 0.547308 | 0.203452 | 0.041* | |
C8 | −0.0093 (3) | 0.39422 (13) | 0.29653 (12) | 0.0313 (6) | |
C9 | 0.0622 (3) | 0.35015 (12) | 0.33978 (11) | 0.0244 (6) | |
H9 | 0.144877 | 0.361404 | 0.367861 | 0.029* | |
C10 | 0.0022 (2) | 0.29007 (12) | 0.33766 (11) | 0.0227 (5) | |
C11 | −0.1273 (3) | 0.36677 (14) | 0.26204 (12) | 0.0375 (7) | |
C12 | −0.2322 (4) | 0.39429 (17) | 0.21049 (14) | 0.0586 (11) | |
H12A | −0.285793 | 0.359079 | 0.187995 | 0.088* | |
H12B | −0.182181 | 0.418385 | 0.184381 | 0.088* | |
H12C | −0.296719 | 0.423286 | 0.225561 | 0.088* | |
C13 | 0.0463 (2) | 0.23530 (11) | 0.37674 (11) | 0.0203 (5) | |
C14 | 0.1695 (2) | 0.23865 (12) | 0.42021 (12) | 0.0257 (6) | |
H14 | 0.228697 | 0.275432 | 0.422169 | 0.031* | |
C15 | 0.2057 (2) | 0.18948 (12) | 0.45998 (12) | 0.0264 (6) | |
H15 | 0.289450 | 0.192398 | 0.489611 | 0.032* | |
C16 | 0.0069 (2) | 0.13015 (12) | 0.41458 (11) | 0.0226 (6) | |
H16 | −0.047981 | 0.091949 | 0.412604 | 0.027* | |
C17 | −0.0326 (3) | 0.17850 (12) | 0.37371 (11) | 0.0227 (5) | |
H17 | −0.114005 | 0.173317 | 0.343149 | 0.027* | |
C18 | 0.1781 (3) | 0.47647 (12) | 0.29621 (11) | 0.0246 (6) | |
C19 | 0.2292 (2) | 0.54439 (12) | 0.30492 (11) | 0.0235 (6) | |
C20 | 0.3195 (3) | 0.57024 (12) | 0.27074 (12) | 0.0267 (6) | |
H20 | 0.350435 | 0.544255 | 0.241760 | 0.032* | |
C21 | 0.3641 (3) | 0.63368 (13) | 0.27893 (13) | 0.0338 (7) | |
H21 | 0.422774 | 0.651445 | 0.254500 | 0.041* | |
C22 | 0.3240 (3) | 0.67132 (13) | 0.32231 (13) | 0.0359 (7) | |
H22 | 0.356879 | 0.714473 | 0.328329 | 0.043* | |
C23 | 0.2366 (3) | 0.64622 (14) | 0.35670 (13) | 0.0362 (7) | |
H23 | 0.209044 | 0.671981 | 0.386651 | 0.043* | |
C24 | 0.1884 (3) | 0.58343 (13) | 0.34779 (12) | 0.0305 (6) | |
H24 | 0.126525 | 0.566719 | 0.371320 | 0.037* | |
C25 | 0.2857 (3) | 0.42554 (12) | 0.29630 (11) | 0.0269 (6) | |
C26 | 0.4077 (3) | 0.41702 (12) | 0.34235 (12) | 0.0257 (6) | |
H26 | 0.435689 | 0.446931 | 0.373914 | 0.031* | |
C27 | 0.4804 (3) | 0.36154 (12) | 0.33657 (12) | 0.0268 (6) | |
C28 | 0.2741 (3) | 0.37826 (13) | 0.25334 (12) | 0.0331 (7) | |
C29 | 0.1682 (4) | 0.37222 (16) | 0.19656 (13) | 0.0495 (9) | |
H29A | 0.214791 | 0.357191 | 0.164932 | 0.074* | |
H29B | 0.124643 | 0.414341 | 0.185643 | 0.074* | |
H29C | 0.095499 | 0.341146 | 0.201817 | 0.074* | |
C30 | 0.6010 (3) | 0.33471 (12) | 0.37813 (12) | 0.0278 (6) | |
C31 | 0.7110 (3) | 0.37435 (12) | 0.40597 (13) | 0.0313 (7) | |
H31 | 0.709933 | 0.419035 | 0.396651 | 0.038* | |
C32 | 0.8206 (3) | 0.34897 (13) | 0.44674 (13) | 0.0342 (7) | |
H32 | 0.896227 | 0.375891 | 0.465211 | 0.041* | |
C33 | 0.7178 (3) | 0.24573 (13) | 0.43437 (13) | 0.0326 (7) | |
H33 | 0.721274 | 0.201370 | 0.445009 | 0.039* | |
C34 | 0.6086 (3) | 0.26863 (12) | 0.39270 (13) | 0.0292 (6) | |
H34 | 0.537375 | 0.239972 | 0.373384 | 0.035* | |
O1 | 0.15288 (15) | 0.44436 (7) | 0.05522 (7) | 0.0184 (4) | |
O2 | 0.21095 (15) | 0.51778 (7) | 0.12654 (7) | 0.0181 (4) | |
O3 | 0.50248 (16) | 0.28625 (8) | 0.04513 (8) | 0.0259 (4) | |
O4 | 0.73232 (16) | 0.30715 (8) | 0.07405 (8) | 0.0268 (4) | |
O5 | 0.90758 (15) | 0.45893 (8) | 0.08324 (8) | 0.0234 (4) | |
O6 | 0.81109 (16) | 0.40799 (8) | −0.00158 (8) | 0.0224 (4) | |
O7 | 0.38082 (16) | 0.60843 (7) | 0.13183 (7) | 0.0190 (4) | |
O8 | 0.55012 (16) | 0.63336 (7) | 0.08472 (8) | 0.0238 (4) | |
C35 | 0.3937 (2) | 0.47203 (10) | 0.08302 (10) | 0.0132 (5) | |
C36 | 0.4346 (2) | 0.40920 (11) | 0.07359 (10) | 0.0149 (5) | |
H36 | 0.368379 | 0.375342 | 0.073080 | 0.018* | |
C37 | 0.5685 (2) | 0.39396 (10) | 0.06489 (10) | 0.0132 (5) | |
C38 | 0.6634 (2) | 0.44423 (10) | 0.06299 (10) | 0.0136 (5) | |
C39 | 0.6253 (2) | 0.50668 (10) | 0.07430 (10) | 0.0133 (5) | |
H39 | 0.691680 | 0.540377 | 0.074305 | 0.016* | |
C40 | 0.4927 (2) | 0.52210 (10) | 0.08573 (10) | 0.0138 (5) | |
C41 | 0.2416 (2) | 0.47977 (10) | 0.08863 (10) | 0.0143 (5) | |
C42 | 0.6097 (2) | 0.32426 (11) | 0.06106 (10) | 0.0181 (5) | |
C43 | 0.8022 (2) | 0.43356 (10) | 0.04492 (10) | 0.0139 (5) | |
C44 | 0.4741 (2) | 0.59280 (11) | 0.09972 (10) | 0.0160 (5) | |
O9 | 0.45208 (18) | 0.67173 (8) | 0.47900 (8) | 0.0289 (4) | |
C45 | 0.5525 (3) | 0.63535 (12) | 0.47802 (14) | 0.0323 (7) | |
C46 | 0.5325 (2) | 0.56472 (11) | 0.48966 (11) | 0.0169 (5) | |
C47 | 0.3945 (2) | 0.54433 (11) | 0.48699 (10) | 0.0161 (5) | |
H47 | 0.321071 | 0.575283 | 0.477791 | 0.019* | |
C48 | 0.3590 (2) | 0.48103 (10) | 0.49711 (10) | 0.0160 (5) | |
C49 | 0.2032 (2) | 0.46755 (12) | 0.49153 (11) | 0.0223 (6) | |
O10 | 0.6569 (9) | 0.6481 (4) | 0.4515 (5) | 0.092 (4) | 0.517 (6) |
H10 | 0.728844 | 0.628059 | 0.468870 | 0.111* | 0.517 (6) |
O11 | 0.1491 (3) | 0.49767 (18) | 0.5307 (2) | 0.0320 (15) | 0.517 (6) |
O12 | 0.1480 (7) | 0.4251 (4) | 0.4603 (4) | 0.077 (3) | 0.517 (6) |
O10A | 0.6684 (7) | 0.6620 (4) | 0.4854 (4) | 0.050 (2) | 0.483 (6) |
H1 | 0.143 (3) | 0.1077 (13) | 0.4871 (11) | 0.060* | |
H2 | 0.894 (3) | 0.2701 (15) | 0.4915 (12) | 0.060* | |
H3A | 0.524 (3) | 0.2459 (10) | 0.0390 (14) | 0.060* | |
H5A | 0.985 (2) | 0.4531 (16) | 0.0717 (14) | 0.060* | |
H7A | 0.326 (3) | 0.5760 (12) | 0.1344 (14) | 0.060* | |
O11A | 0.1230 (3) | 0.51944 (16) | 0.4805 (2) | 0.0268 (15) | 0.483 (6) |
H11A | 0.038373 | 0.508693 | 0.477692 | 0.032* | 0.483 (6) |
O12A | 0.1465 (5) | 0.4153 (2) | 0.4920 (3) | 0.0298 (15) | 0.483 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0413 (4) | 0.0342 (4) | 0.0249 (4) | −0.0183 (3) | −0.0053 (3) | 0.0063 (3) |
S2 | 0.0598 (5) | 0.0218 (4) | 0.0366 (4) | −0.0038 (3) | 0.0190 (4) | −0.0062 (3) |
N1 | 0.0177 (10) | 0.0158 (11) | 0.0360 (13) | 0.0020 (8) | 0.0115 (10) | 0.0038 (9) |
N2 | 0.0327 (13) | 0.0291 (14) | 0.0467 (16) | 0.0077 (11) | 0.0189 (11) | −0.0064 (12) |
C1 | 0.0358 (15) | 0.0289 (15) | 0.0211 (14) | −0.0080 (12) | 0.0003 (12) | 0.0090 (12) |
C2 | 0.0262 (14) | 0.0385 (17) | 0.0334 (16) | −0.0078 (12) | −0.0016 (12) | 0.0155 (13) |
C3 | 0.0358 (17) | 0.072 (2) | 0.057 (2) | 0.0049 (16) | 0.0161 (16) | 0.0405 (19) |
C4 | 0.043 (2) | 0.123 (4) | 0.091 (3) | 0.029 (2) | 0.036 (2) | 0.068 (3) |
C5 | 0.0360 (19) | 0.107 (3) | 0.093 (3) | 0.029 (2) | 0.024 (2) | 0.066 (3) |
C6 | 0.0257 (15) | 0.066 (2) | 0.053 (2) | 0.0020 (15) | 0.0043 (14) | 0.0357 (18) |
C7 | 0.0256 (14) | 0.0378 (17) | 0.0352 (16) | −0.0088 (12) | −0.0012 (12) | 0.0149 (13) |
C8 | 0.0329 (14) | 0.0335 (16) | 0.0248 (14) | −0.0120 (12) | −0.0004 (12) | 0.0080 (12) |
C9 | 0.0260 (13) | 0.0264 (14) | 0.0196 (13) | −0.0065 (11) | 0.0017 (11) | 0.0026 (11) |
C10 | 0.0244 (13) | 0.0242 (14) | 0.0191 (13) | −0.0071 (11) | 0.0037 (10) | 0.0011 (11) |
C11 | 0.0459 (17) | 0.0363 (17) | 0.0253 (15) | −0.0151 (14) | −0.0044 (13) | 0.0152 (13) |
C12 | 0.061 (2) | 0.061 (2) | 0.0391 (19) | −0.0274 (18) | −0.0242 (17) | 0.0276 (17) |
C13 | 0.0209 (12) | 0.0206 (13) | 0.0218 (13) | −0.0019 (10) | 0.0097 (10) | −0.0014 (11) |
C14 | 0.0193 (12) | 0.0195 (13) | 0.0389 (16) | −0.0055 (10) | 0.0070 (11) | 0.0032 (12) |
C15 | 0.0157 (12) | 0.0222 (14) | 0.0413 (16) | −0.0012 (10) | 0.0054 (11) | 0.0051 (12) |
C16 | 0.0204 (13) | 0.0192 (13) | 0.0318 (15) | −0.0025 (10) | 0.0140 (11) | −0.0050 (11) |
C17 | 0.0226 (12) | 0.0222 (14) | 0.0247 (13) | −0.0053 (10) | 0.0081 (11) | −0.0037 (11) |
C18 | 0.0330 (14) | 0.0220 (14) | 0.0180 (13) | −0.0056 (11) | 0.0034 (11) | 0.0049 (11) |
C19 | 0.0222 (12) | 0.0220 (14) | 0.0228 (14) | 0.0011 (10) | −0.0035 (11) | 0.0035 (11) |
C20 | 0.0272 (13) | 0.0223 (14) | 0.0298 (15) | −0.0014 (11) | 0.0037 (12) | 0.0012 (11) |
C21 | 0.0297 (14) | 0.0241 (15) | 0.0458 (18) | −0.0036 (12) | 0.0035 (13) | 0.0056 (13) |
C22 | 0.0392 (16) | 0.0189 (14) | 0.0424 (18) | 0.0008 (12) | −0.0085 (14) | −0.0020 (13) |
C23 | 0.0459 (17) | 0.0288 (16) | 0.0311 (16) | 0.0055 (13) | 0.0011 (14) | −0.0035 (13) |
C24 | 0.0329 (15) | 0.0303 (16) | 0.0276 (15) | 0.0028 (12) | 0.0046 (12) | 0.0036 (12) |
C25 | 0.0381 (15) | 0.0185 (14) | 0.0264 (15) | −0.0077 (11) | 0.0123 (12) | 0.0037 (11) |
C26 | 0.0335 (14) | 0.0161 (13) | 0.0308 (15) | −0.0054 (11) | 0.0142 (12) | 0.0002 (11) |
C27 | 0.0359 (15) | 0.0157 (13) | 0.0329 (15) | −0.0068 (11) | 0.0166 (12) | 0.0003 (11) |
C28 | 0.0517 (18) | 0.0237 (15) | 0.0267 (15) | −0.0076 (13) | 0.0148 (13) | 0.0009 (12) |
C29 | 0.078 (2) | 0.0433 (19) | 0.0258 (16) | −0.0093 (17) | 0.0067 (16) | −0.0002 (14) |
C30 | 0.0322 (14) | 0.0189 (13) | 0.0395 (16) | −0.0007 (11) | 0.0242 (13) | −0.0028 (12) |
C31 | 0.0354 (15) | 0.0170 (14) | 0.0495 (18) | −0.0029 (12) | 0.0274 (14) | −0.0035 (13) |
C32 | 0.0304 (15) | 0.0235 (15) | 0.0547 (19) | −0.0036 (12) | 0.0225 (14) | −0.0124 (14) |
C33 | 0.0356 (15) | 0.0182 (14) | 0.0498 (18) | 0.0004 (12) | 0.0226 (14) | −0.0016 (13) |
C34 | 0.0329 (15) | 0.0162 (13) | 0.0439 (17) | −0.0026 (11) | 0.0206 (13) | −0.0046 (12) |
O1 | 0.0083 (7) | 0.0158 (9) | 0.0315 (10) | −0.0015 (6) | 0.0049 (7) | −0.0051 (7) |
O2 | 0.0138 (8) | 0.0151 (9) | 0.0269 (9) | 0.0012 (7) | 0.0078 (7) | −0.0035 (7) |
O3 | 0.0139 (8) | 0.0087 (8) | 0.0538 (12) | 0.0008 (7) | 0.0041 (8) | −0.0041 (8) |
O4 | 0.0118 (8) | 0.0164 (9) | 0.0523 (12) | 0.0046 (7) | 0.0066 (8) | 0.0033 (8) |
O5 | 0.0079 (8) | 0.0319 (10) | 0.0310 (10) | −0.0019 (7) | 0.0058 (7) | −0.0091 (8) |
O6 | 0.0160 (8) | 0.0237 (9) | 0.0297 (10) | −0.0014 (7) | 0.0097 (7) | −0.0061 (8) |
O7 | 0.0157 (8) | 0.0123 (8) | 0.0310 (10) | 0.0004 (6) | 0.0092 (7) | −0.0048 (7) |
O8 | 0.0226 (9) | 0.0114 (9) | 0.0399 (11) | −0.0025 (7) | 0.0123 (8) | −0.0005 (8) |
C35 | 0.0093 (10) | 0.0124 (12) | 0.0178 (12) | 0.0005 (9) | 0.0025 (9) | 0.0015 (9) |
C36 | 0.0122 (11) | 0.0105 (12) | 0.0220 (13) | −0.0025 (9) | 0.0034 (10) | 0.0013 (10) |
C37 | 0.0104 (10) | 0.0116 (11) | 0.0172 (12) | 0.0013 (9) | 0.0016 (9) | 0.0008 (9) |
C38 | 0.0107 (10) | 0.0133 (12) | 0.0159 (12) | 0.0004 (9) | 0.0007 (9) | 0.0002 (10) |
C39 | 0.0101 (10) | 0.0113 (11) | 0.0180 (12) | −0.0030 (9) | 0.0012 (9) | −0.0003 (9) |
C40 | 0.0122 (10) | 0.0110 (11) | 0.0177 (12) | 0.0017 (9) | 0.0013 (9) | 0.0007 (9) |
C41 | 0.0118 (10) | 0.0076 (11) | 0.0239 (13) | 0.0016 (9) | 0.0042 (10) | 0.0032 (10) |
C42 | 0.0163 (12) | 0.0139 (12) | 0.0253 (13) | −0.0003 (10) | 0.0070 (10) | 0.0015 (10) |
C43 | 0.0106 (11) | 0.0087 (11) | 0.0228 (13) | 0.0002 (9) | 0.0039 (10) | 0.0019 (10) |
C44 | 0.0118 (11) | 0.0140 (12) | 0.0213 (13) | 0.0017 (9) | 0.0014 (10) | 0.0002 (10) |
O9 | 0.0304 (10) | 0.0128 (9) | 0.0475 (12) | 0.0068 (8) | 0.0173 (9) | 0.0034 (8) |
C45 | 0.0226 (14) | 0.0143 (13) | 0.0575 (19) | −0.0016 (11) | 0.0020 (13) | 0.0064 (13) |
C46 | 0.0156 (11) | 0.0103 (11) | 0.0272 (14) | 0.0002 (9) | 0.0102 (10) | −0.0004 (10) |
C47 | 0.0132 (11) | 0.0114 (12) | 0.0246 (13) | 0.0031 (9) | 0.0060 (10) | −0.0020 (10) |
C48 | 0.0122 (10) | 0.0109 (12) | 0.0266 (13) | −0.0009 (9) | 0.0079 (10) | −0.0035 (10) |
C49 | 0.0173 (12) | 0.0208 (14) | 0.0306 (15) | −0.0055 (11) | 0.0091 (11) | −0.0069 (12) |
O10 | 0.069 (5) | 0.026 (4) | 0.218 (11) | 0.018 (3) | 0.112 (7) | 0.044 (5) |
O11 | 0.0183 (18) | 0.030 (2) | 0.052 (3) | −0.0083 (15) | 0.0172 (18) | −0.020 (2) |
O12 | 0.040 (3) | 0.106 (6) | 0.096 (6) | −0.050 (3) | 0.042 (4) | −0.080 (5) |
O10A | 0.011 (2) | 0.018 (3) | 0.117 (6) | −0.007 (2) | 0.001 (3) | 0.005 (3) |
O11A | 0.0072 (16) | 0.012 (2) | 0.063 (4) | −0.0017 (14) | 0.0115 (18) | 0.0024 (19) |
O12A | 0.010 (2) | 0.007 (2) | 0.072 (4) | −0.0014 (15) | 0.009 (3) | 0.007 (3) |
S1—C10 | 1.735 (2) | C25—C28 | 1.378 (4) |
S1—C11 | 1.720 (3) | C26—H26 | 0.9500 |
S2—C27 | 1.727 (3) | C26—C27 | 1.369 (3) |
S2—C28 | 1.725 (3) | C27—C30 | 1.460 (4) |
N1—C15 | 1.347 (3) | C28—C29 | 1.492 (4) |
N1—C16 | 1.344 (3) | C29—H29A | 0.9800 |
N1—H1 | 0.902 (18) | C29—H29B | 0.9800 |
N2—C32 | 1.344 (3) | C29—H29C | 0.9800 |
N2—C33 | 1.347 (3) | C30—C31 | 1.395 (4) |
N2—H2 | 0.953 (18) | C30—C34 | 1.408 (3) |
C1—C2 | 1.486 (4) | C31—H31 | 0.9500 |
C1—C8 | 1.489 (4) | C31—C32 | 1.371 (4) |
C1—C18 | 1.357 (4) | C32—H32 | 0.9500 |
C2—C3 | 1.389 (4) | C33—H33 | 0.9500 |
C2—C7 | 1.391 (4) | C33—C34 | 1.360 (4) |
C3—H3 | 0.9500 | C34—H34 | 0.9500 |
C3—C4 | 1.386 (5) | O1—C41 | 1.265 (3) |
C4—H4 | 0.9500 | O2—C41 | 1.253 (3) |
C4—C5 | 1.386 (5) | O3—C42 | 1.297 (3) |
C5—H5 | 0.9500 | O3—H3A | 0.880 (18) |
C5—C6 | 1.372 (5) | O4—C42 | 1.219 (3) |
C6—H6 | 0.9500 | O5—C43 | 1.315 (3) |
C6—C7 | 1.381 (4) | O5—H5A | 0.854 (18) |
C7—H7 | 0.9500 | O6—C43 | 1.209 (3) |
C8—C9 | 1.421 (3) | O7—C44 | 1.317 (3) |
C8—C11 | 1.376 (4) | O7—H7A | 0.867 (18) |
C9—H9 | 0.9500 | O8—C44 | 1.213 (3) |
C9—C10 | 1.371 (3) | C35—C36 | 1.391 (3) |
C10—C13 | 1.456 (3) | C35—C40 | 1.407 (3) |
C11—C12 | 1.507 (4) | C35—C41 | 1.516 (3) |
C12—H12A | 0.9800 | C36—H36 | 0.9500 |
C12—H12B | 0.9800 | C36—C37 | 1.389 (3) |
C12—H12C | 0.9800 | C37—C38 | 1.397 (3) |
C13—C14 | 1.394 (3) | C37—C42 | 1.506 (3) |
C13—C17 | 1.398 (3) | C38—C39 | 1.385 (3) |
C14—H14 | 0.9500 | C38—C43 | 1.503 (3) |
C14—C15 | 1.365 (3) | C39—H39 | 0.9500 |
C15—H15 | 0.9500 | C39—C40 | 1.400 (3) |
C16—H16 | 0.9500 | C40—C44 | 1.519 (3) |
C16—C17 | 1.372 (3) | O9—C45 | 1.236 (3) |
C17—H17 | 0.9500 | C45—C46 | 1.507 (3) |
C18—C19 | 1.492 (3) | C45—O10 | 1.310 (7) |
C18—C25 | 1.484 (4) | C45—O10A | 1.233 (7) |
C19—C20 | 1.395 (4) | C46—C47 | 1.393 (3) |
C19—C24 | 1.391 (4) | C46—C48i | 1.403 (3) |
C20—H20 | 0.9500 | C47—H47 | 0.9500 |
C20—C21 | 1.385 (4) | C47—C48 | 1.388 (3) |
C21—H21 | 0.9500 | C48—C49 | 1.517 (3) |
C21—C22 | 1.380 (4) | C49—O11 | 1.289 (4) |
C22—H22 | 0.9500 | C49—O12 | 1.190 (6) |
C22—C23 | 1.372 (4) | C49—O11A | 1.321 (4) |
C23—H23 | 0.9500 | C49—O12A | 1.215 (6) |
C23—C24 | 1.384 (4) | O10—H10 | 0.8402 |
C24—H24 | 0.9500 | O11A—H11A | 0.8400 |
C25—C26 | 1.428 (4) | ||
C11—S1—C10 | 92.52 (12) | C25—C26—H26 | 123.3 |
C28—S2—C27 | 92.51 (13) | C27—C26—C25 | 113.5 (2) |
C15—N1—H1 | 118 (2) | C27—C26—H26 | 123.3 |
C16—N1—C15 | 121.2 (2) | C26—C27—S2 | 110.7 (2) |
C16—N1—H1 | 120 (2) | C26—C27—C30 | 128.1 (2) |
C32—N2—C33 | 122.1 (3) | C30—C27—S2 | 121.22 (19) |
C32—N2—H2 | 118 (2) | C25—C28—S2 | 111.1 (2) |
C33—N2—H2 | 119 (2) | C25—C28—C29 | 128.7 (3) |
C2—C1—C8 | 115.9 (2) | C29—C28—S2 | 120.1 (2) |
C18—C1—C2 | 121.9 (2) | C28—C29—H29A | 109.5 |
C18—C1—C8 | 122.2 (2) | C28—C29—H29B | 109.5 |
C3—C2—C1 | 121.3 (2) | C28—C29—H29C | 109.5 |
C3—C2—C7 | 118.8 (3) | H29A—C29—H29B | 109.5 |
C7—C2—C1 | 119.8 (3) | H29A—C29—H29C | 109.5 |
C2—C3—H3 | 119.6 | H29B—C29—H29C | 109.5 |
C4—C3—C2 | 120.9 (3) | C31—C30—C27 | 120.8 (2) |
C4—C3—H3 | 119.6 | C31—C30—C34 | 117.7 (2) |
C3—C4—H4 | 120.4 | C34—C30—C27 | 121.5 (2) |
C3—C4—C5 | 119.1 (3) | C30—C31—H31 | 119.9 |
C5—C4—H4 | 120.4 | C32—C31—C30 | 120.1 (2) |
C4—C5—H5 | 119.7 | C32—C31—H31 | 119.9 |
C6—C5—C4 | 120.7 (3) | N2—C32—C31 | 119.9 (3) |
C6—C5—H5 | 119.7 | N2—C32—H32 | 120.1 |
C5—C6—H6 | 120.0 | C31—C32—H32 | 120.1 |
C5—C6—C7 | 120.1 (3) | N2—C33—H33 | 120.0 |
C7—C6—H6 | 120.0 | N2—C33—C34 | 120.0 (2) |
C2—C7—H7 | 119.8 | C34—C33—H33 | 120.0 |
C6—C7—C2 | 120.4 (3) | C30—C34—H34 | 119.9 |
C6—C7—H7 | 119.8 | C33—C34—C30 | 120.2 (3) |
C9—C8—C1 | 123.1 (2) | C33—C34—H34 | 119.9 |
C11—C8—C1 | 125.4 (2) | C42—O3—H3A | 115 (2) |
C11—C8—C9 | 111.5 (2) | C43—O5—H5A | 110 (2) |
C8—C9—H9 | 122.7 | C44—O7—H7A | 110 (2) |
C10—C9—C8 | 114.5 (2) | C36—C35—C40 | 118.93 (19) |
C10—C9—H9 | 122.7 | C36—C35—C41 | 115.20 (18) |
C9—C10—S1 | 109.72 (18) | C40—C35—C41 | 125.86 (19) |
C9—C10—C13 | 128.1 (2) | C35—C36—H36 | 118.7 |
C13—C10—S1 | 122.15 (18) | C37—C36—C35 | 122.7 (2) |
C8—C11—S1 | 111.7 (2) | C37—C36—H36 | 118.7 |
C8—C11—C12 | 130.2 (3) | C36—C37—C38 | 118.4 (2) |
C12—C11—S1 | 118.1 (2) | C36—C37—C42 | 119.55 (19) |
C11—C12—H12A | 109.5 | C38—C37—C42 | 121.95 (19) |
C11—C12—H12B | 109.5 | C37—C38—C43 | 122.12 (19) |
C11—C12—H12C | 109.5 | C39—C38—C37 | 119.25 (19) |
H12A—C12—H12B | 109.5 | C39—C38—C43 | 118.49 (19) |
H12A—C12—H12C | 109.5 | C38—C39—H39 | 118.7 |
H12B—C12—H12C | 109.5 | C38—C39—C40 | 122.6 (2) |
C14—C13—C10 | 120.2 (2) | C40—C39—H39 | 118.7 |
C14—C13—C17 | 117.3 (2) | C35—C40—C44 | 127.71 (19) |
C17—C13—C10 | 122.4 (2) | C39—C40—C35 | 117.89 (19) |
C13—C14—H14 | 119.8 | C39—C40—C44 | 114.39 (19) |
C15—C14—C13 | 120.5 (2) | O1—C41—C35 | 116.21 (19) |
C15—C14—H14 | 119.8 | O2—C41—O1 | 123.90 (19) |
N1—C15—C14 | 120.4 (2) | O2—C41—C35 | 119.82 (19) |
N1—C15—H15 | 119.8 | O3—C42—C37 | 113.07 (18) |
C14—C15—H15 | 119.8 | O4—C42—O3 | 125.4 (2) |
N1—C16—H16 | 120.0 | O4—C42—C37 | 121.5 (2) |
N1—C16—C17 | 120.0 (2) | O5—C43—C38 | 112.03 (19) |
C17—C16—H16 | 120.0 | O6—C43—O5 | 125.5 (2) |
C13—C17—H17 | 119.8 | O6—C43—C38 | 122.35 (19) |
C16—C17—C13 | 120.4 (2) | O7—C44—C40 | 118.68 (19) |
C16—C17—H17 | 119.8 | O8—C44—O7 | 120.9 (2) |
C1—C18—C19 | 121.5 (2) | O8—C44—C40 | 120.2 (2) |
C1—C18—C25 | 121.3 (2) | O9—C45—C46 | 117.3 (2) |
C25—C18—C19 | 117.1 (2) | O9—C45—O10 | 124.9 (4) |
C20—C19—C18 | 121.1 (2) | O10—C45—C46 | 114.7 (4) |
C24—C19—C18 | 120.6 (2) | O10A—C45—O9 | 115.2 (4) |
C24—C19—C20 | 118.3 (2) | O10A—C45—C46 | 123.8 (4) |
C19—C20—H20 | 119.9 | C47—C46—C45 | 116.3 (2) |
C21—C20—C19 | 120.2 (3) | C47—C46—C48i | 118.4 (2) |
C21—C20—H20 | 119.9 | C48i—C46—C45 | 125.2 (2) |
C20—C21—H21 | 119.7 | C46—C47—H47 | 118.4 |
C22—C21—C20 | 120.6 (3) | C48—C47—C46 | 123.2 (2) |
C22—C21—H21 | 119.7 | C48—C47—H47 | 118.4 |
C21—C22—H22 | 120.1 | C46i—C48—C49 | 125.8 (2) |
C23—C22—C21 | 119.8 (3) | C47—C48—C46i | 118.34 (19) |
C23—C22—H22 | 120.1 | C47—C48—C49 | 115.89 (19) |
C22—C23—H23 | 120.0 | O11—C49—C48 | 113.0 (2) |
C22—C23—C24 | 120.1 (3) | O12—C49—C48 | 120.4 (4) |
C24—C23—H23 | 120.0 | O12—C49—O11 | 125.5 (4) |
C19—C24—H24 | 119.5 | O11A—C49—C48 | 113.8 (2) |
C23—C24—C19 | 121.0 (3) | O12A—C49—C48 | 127.5 (3) |
C23—C24—H24 | 119.5 | O12A—C49—O11A | 118.5 (3) |
C26—C25—C18 | 124.5 (2) | C45—O10—H10 | 108.9 |
C28—C25—C18 | 123.3 (2) | C49—O11A—H11A | 109.1 |
C28—C25—C26 | 112.1 (2) | ||
S1—C10—C13—C14 | 178.23 (19) | C25—C26—C27—C30 | −173.7 (2) |
S1—C10—C13—C17 | −3.3 (3) | C26—C25—C28—S2 | 4.0 (3) |
S2—C27—C30—C31 | 140.1 (2) | C26—C25—C28—C29 | −175.7 (3) |
S2—C27—C30—C34 | −41.6 (3) | C26—C27—C30—C31 | −43.2 (4) |
N1—C16—C17—C13 | −0.9 (4) | C26—C27—C30—C34 | 135.1 (3) |
N2—C33—C34—C30 | −1.9 (4) | C27—S2—C28—C25 | −1.8 (2) |
C1—C2—C3—C4 | −175.0 (3) | C27—S2—C28—C29 | 177.9 (2) |
C1—C2—C7—C6 | 174.7 (3) | C27—C30—C31—C32 | 177.3 (2) |
C1—C8—C9—C10 | −179.0 (3) | C27—C30—C34—C33 | −175.8 (2) |
C1—C8—C11—S1 | 179.0 (2) | C28—S2—C27—C26 | −0.9 (2) |
C1—C8—C11—C12 | 1.8 (6) | C28—S2—C27—C30 | 176.3 (2) |
C1—C18—C19—C20 | −131.6 (3) | C28—C25—C26—C27 | −4.8 (3) |
C1—C18—C19—C24 | 48.8 (3) | C30—C31—C32—N2 | −1.0 (4) |
C1—C18—C25—C26 | −124.9 (3) | C31—C30—C34—C33 | 2.5 (4) |
C1—C18—C25—C28 | 50.8 (4) | C32—N2—C33—C34 | −0.2 (4) |
C2—C1—C8—C9 | −141.4 (3) | C33—N2—C32—C31 | 1.7 (4) |
C2—C1—C8—C11 | 38.4 (4) | C34—C30—C31—C32 | −1.1 (4) |
C2—C1—C18—C19 | 16.4 (4) | C35—C36—C37—C38 | −2.9 (3) |
C2—C1—C18—C25 | −166.0 (2) | C35—C36—C37—C42 | 173.9 (2) |
C2—C3—C4—C5 | −0.2 (7) | C35—C40—C44—O7 | 25.3 (3) |
C3—C2—C7—C6 | −1.8 (4) | C35—C40—C44—O8 | −159.3 (2) |
C3—C4—C5—C6 | −0.8 (7) | C36—C35—C40—C39 | 4.7 (3) |
C4—C5—C6—C7 | 0.4 (6) | C36—C35—C40—C44 | −175.5 (2) |
C5—C6—C7—C2 | 0.9 (5) | C36—C35—C41—O1 | −37.4 (3) |
C7—C2—C3—C4 | 1.4 (5) | C36—C35—C41—O2 | 139.9 (2) |
C8—C1—C2—C3 | 52.6 (4) | C36—C37—C38—C39 | 4.9 (3) |
C8—C1—C2—C7 | −123.8 (3) | C36—C37—C38—C43 | −170.8 (2) |
C8—C1—C18—C19 | −164.9 (2) | C36—C37—C42—O3 | 23.5 (3) |
C8—C1—C18—C25 | 12.7 (4) | C36—C37—C42—O4 | −154.1 (2) |
C8—C9—C10—S1 | −0.7 (3) | C37—C38—C39—C40 | −2.2 (3) |
C8—C9—C10—C13 | −177.6 (2) | C37—C38—C43—O5 | −130.1 (2) |
C9—C8—C11—S1 | −1.2 (3) | C37—C38—C43—O6 | 54.2 (3) |
C9—C8—C11—C12 | −178.4 (3) | C38—C37—C42—O3 | −159.9 (2) |
C9—C10—C13—C14 | −5.2 (4) | C38—C37—C42—O4 | 22.5 (3) |
C9—C10—C13—C17 | 173.2 (2) | C38—C39—C40—C35 | −2.7 (3) |
C10—S1—C11—C8 | 0.7 (2) | C38—C39—C40—C44 | 177.5 (2) |
C10—S1—C11—C12 | 178.3 (3) | C39—C38—C43—O5 | 54.1 (3) |
C10—C13—C14—C15 | 174.9 (2) | C39—C38—C43—O6 | −121.6 (2) |
C10—C13—C17—C16 | −174.6 (2) | C39—C40—C44—O7 | −154.8 (2) |
C11—S1—C10—C9 | 0.0 (2) | C39—C40—C44—O8 | 20.5 (3) |
C11—S1—C10—C13 | 177.1 (2) | C40—C35—C36—C37 | −2.0 (3) |
C11—C8—C9—C10 | 1.3 (4) | C40—C35—C41—O1 | 141.7 (2) |
C13—C14—C15—N1 | 0.5 (4) | C40—C35—C41—O2 | −41.0 (3) |
C14—C13—C17—C16 | 3.9 (3) | C41—C35—C36—C37 | 177.1 (2) |
C15—N1—C16—C17 | −2.4 (3) | C41—C35—C40—C39 | −174.4 (2) |
C16—N1—C15—C14 | 2.6 (4) | C41—C35—C40—C44 | 5.5 (4) |
C17—C13—C14—C15 | −3.6 (4) | C42—C37—C38—C39 | −171.8 (2) |
C18—C1—C2—C3 | −128.6 (3) | C42—C37—C38—C43 | 12.5 (3) |
C18—C1—C2—C7 | 55.0 (4) | C43—C38—C39—C40 | 173.7 (2) |
C18—C1—C8—C9 | 39.8 (4) | O9—C45—C46—C47 | 14.2 (4) |
C18—C1—C8—C11 | −140.4 (3) | O9—C45—C46—C48i | −165.6 (2) |
C18—C19—C20—C21 | 179.1 (2) | C45—C46—C47—C48 | −179.5 (2) |
C18—C19—C24—C23 | 179.2 (2) | C46—C47—C48—C46i | −0.4 (4) |
C18—C25—C26—C27 | 171.3 (2) | C46—C47—C48—C49 | −179.3 (2) |
C18—C25—C28—S2 | −172.17 (19) | C46i—C48—C49—O11 | 117.2 (3) |
C18—C25—C28—C29 | 8.2 (4) | C46i—C48—C49—O12 | −51.2 (7) |
C19—C18—C25—C26 | 52.8 (3) | C46i—C48—C49—O11A | 178.1 (3) |
C19—C18—C25—C28 | −131.5 (3) | C46i—C48—C49—O12A | −7.4 (6) |
C19—C20—C21—C22 | 2.3 (4) | C47—C48—C49—O11 | −64.0 (4) |
C20—C19—C24—C23 | −0.4 (4) | C47—C48—C49—O12 | 127.6 (6) |
C20—C21—C22—C23 | −1.5 (4) | C47—C48—C49—O11A | −3.1 (4) |
C21—C22—C23—C24 | −0.2 (4) | C47—C48—C49—O12A | 171.4 (5) |
C22—C23—C24—C19 | 1.2 (4) | C48i—C46—C47—C48 | 0.4 (4) |
C24—C19—C20—C21 | −1.3 (4) | O10—C45—C46—C47 | −146.9 (6) |
C25—C18—C19—C20 | 50.7 (3) | O10—C45—C46—C48i | 33.3 (7) |
C25—C18—C19—C24 | −128.9 (3) | O10A—C45—C46—C47 | 171.4 (5) |
C25—C26—C27—S2 | 3.3 (3) | O10A—C45—C46—C48i | −8.4 (6) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1ii | 0.90 (2) | 1.88 (2) | 2.772 (3) | 168 (3) |
O3—H3A···O9iii | 0.88 (2) | 1.62 (2) | 2.496 (2) | 173 (3) |
O5—H5A···O1iv | 0.85 (2) | 1.75 (2) | 2.605 (2) | 174 (3) |
O7—H7A···O2 | 0.87 (2) | 1.63 (2) | 2.485 (2) | 170 (3) |
O11A—H11A···O11Av | 0.84 | 2.08 | 2.829 (7) | 149 |
Symmetry codes: (ii) x, −y+1/2, z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) x+1, y, z; (v) −x, −y+1, −z+1. |
C34H26N2S2·C8H6O4 | Dx = 1.278 Mg m−3 |
Mr = 692.81 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 9888 reflections |
a = 30.6739 (12) Å | θ = 2.2–28.7° |
b = 9.6686 (4) Å | µ = 0.19 mm−1 |
c = 24.2850 (9) Å | T = 90 K |
V = 7202.3 (5) Å3 | Plate, colourless |
Z = 8 | 0.2 × 0.16 × 0.02 mm |
F(000) = 2896 |
Bruker APEX-II CCD diffractometer | 19739 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.057 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1275 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.9397. The λ/2 correction factor is Not present. | θmax = 30.5°, θmin = 1.3° |
Tmin = 0.702, Tmax = 0.747 | h = −43→43 |
162249 measured reflections | k = −13→13 |
21979 independent reflections | l = −34→34 |
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)] = 0.036 | w = 1/[σ2(Fo2) + (0.0444P)2 + 1.5553P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.088 | (Δ/σ)max = 0.004 |
S = 1.03 | Δρmax = 0.28 e Å−3 |
21979 reflections | Δρmin = −0.21 e Å−3 |
919 parameters | Absolute structure: Refined as an inversion twin. |
5 restraints | Absolute structure parameter: 0.41 (4) |
Primary atom site location: dual |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.83546 (2) | −0.12898 (6) | 0.73324 (2) | 0.01645 (11) | |
S2 | 0.88049 (2) | −0.09181 (6) | 0.53158 (2) | 0.01615 (10) | |
N1 | 0.89436 (7) | 0.3992 (2) | 0.70858 (9) | 0.0205 (4) | |
N2 | 0.89620 (7) | 0.4314 (2) | 0.45988 (9) | 0.0224 (4) | |
C1 | 0.74856 (7) | −0.2014 (2) | 0.61275 (9) | 0.0139 (4) | |
C2 | 0.70838 (7) | −0.2560 (2) | 0.63986 (9) | 0.0134 (4) | |
C3 | 0.69028 (8) | −0.1811 (2) | 0.68334 (9) | 0.0180 (4) | |
H3 | 0.701649 | −0.092456 | 0.692265 | 0.022* | |
C4 | 0.65584 (8) | −0.2346 (3) | 0.71369 (10) | 0.0207 (5) | |
H4 | 0.643571 | −0.182380 | 0.742992 | 0.025* | |
C5 | 0.63937 (7) | −0.3645 (2) | 0.70111 (10) | 0.0194 (4) | |
H5 | 0.616380 | −0.402456 | 0.722521 | 0.023* | |
C6 | 0.65641 (7) | −0.4389 (2) | 0.65740 (10) | 0.0178 (4) | |
H6 | 0.644690 | −0.527046 | 0.648506 | 0.021* | |
C7 | 0.69066 (7) | −0.3851 (2) | 0.62638 (9) | 0.0145 (4) | |
H7 | 0.701981 | −0.435945 | 0.596115 | 0.017* | |
C8 | 0.78221 (7) | −0.1529 (2) | 0.65244 (9) | 0.0137 (4) | |
C9 | 0.79984 (7) | −0.0171 (2) | 0.64983 (9) | 0.0142 (4) | |
H9 | 0.791942 | 0.047802 | 0.622204 | 0.017* | |
C10 | 0.82905 (7) | 0.0118 (2) | 0.69044 (9) | 0.0137 (4) | |
C11 | 0.79880 (7) | −0.2270 (2) | 0.69593 (9) | 0.0154 (4) | |
C12 | 0.79042 (8) | −0.3749 (2) | 0.71163 (10) | 0.0212 (5) | |
H12A | 0.817034 | −0.415130 | 0.727164 | 0.032* | |
H12B | 0.781724 | −0.427323 | 0.678895 | 0.032* | |
H12C | 0.767029 | −0.378610 | 0.739077 | 0.032* | |
C13 | 0.85187 (7) | 0.1432 (2) | 0.69785 (9) | 0.0140 (4) | |
C14 | 0.85974 (7) | 0.2282 (2) | 0.65203 (10) | 0.0166 (4) | |
H14 | 0.850597 | 0.200487 | 0.616324 | 0.020* | |
C15 | 0.88097 (8) | 0.3527 (2) | 0.65964 (11) | 0.0195 (5) | |
H15 | 0.886368 | 0.408608 | 0.628200 | 0.023* | |
C16 | 0.88689 (8) | 0.3180 (2) | 0.75240 (10) | 0.0213 (5) | |
H16 | 0.896327 | 0.349355 | 0.787513 | 0.026* | |
C17 | 0.86603 (8) | 0.1904 (2) | 0.74914 (9) | 0.0193 (4) | |
H17 | 0.861507 | 0.136364 | 0.781298 | 0.023* | |
C18 | 0.75515 (7) | −0.1856 (2) | 0.55781 (9) | 0.0132 (4) | |
C19 | 0.72139 (7) | −0.2005 (2) | 0.51420 (9) | 0.0151 (4) | |
C20 | 0.73326 (8) | −0.2527 (2) | 0.46235 (10) | 0.0197 (4) | |
H20 | 0.762027 | −0.286062 | 0.456599 | 0.024* | |
C21 | 0.70344 (9) | −0.2559 (3) | 0.41944 (10) | 0.0245 (5) | |
H21 | 0.711701 | −0.292735 | 0.384706 | 0.029* | |
C22 | 0.66141 (9) | −0.2053 (3) | 0.42723 (11) | 0.0243 (5) | |
H22 | 0.641124 | −0.205949 | 0.397670 | 0.029* | |
C23 | 0.64927 (8) | −0.1540 (3) | 0.47821 (11) | 0.0219 (5) | |
H23 | 0.620452 | −0.120704 | 0.483632 | 0.026* | |
C24 | 0.67893 (7) | −0.1509 (2) | 0.52159 (10) | 0.0175 (4) | |
H24 | 0.670313 | −0.114902 | 0.556330 | 0.021* | |
C25 | 0.79829 (7) | −0.1348 (2) | 0.53866 (9) | 0.0136 (4) | |
C26 | 0.80351 (7) | −0.0011 (2) | 0.51391 (9) | 0.0143 (4) | |
H26 | 0.779714 | 0.054448 | 0.502205 | 0.017* | |
C27 | 0.84620 (7) | 0.0384 (2) | 0.50882 (9) | 0.0141 (4) | |
C28 | 0.83755 (7) | −0.1977 (2) | 0.54898 (9) | 0.0153 (4) | |
C29 | 0.84646 (8) | −0.3373 (2) | 0.57329 (10) | 0.0203 (5) | |
H29A | 0.864657 | −0.391021 | 0.547929 | 0.030* | |
H29B | 0.818829 | −0.385923 | 0.579357 | 0.030* | |
H29C | 0.861704 | −0.326412 | 0.608485 | 0.030* | |
C30 | 0.86357 (7) | 0.1716 (2) | 0.49092 (9) | 0.0154 (4) | |
C31 | 0.83840 (8) | 0.2637 (2) | 0.46019 (10) | 0.0194 (4) | |
H31 | 0.809651 | 0.239489 | 0.449300 | 0.023* | |
C32 | 0.85582 (8) | 0.3913 (2) | 0.44569 (11) | 0.0223 (5) | |
H32 | 0.838335 | 0.453090 | 0.424756 | 0.027* | |
C33 | 0.92042 (8) | 0.3429 (3) | 0.48855 (11) | 0.0214 (5) | |
H33 | 0.949182 | 0.369818 | 0.498359 | 0.026* | |
C34 | 0.90591 (8) | 0.2136 (2) | 0.50486 (10) | 0.0186 (4) | |
H34 | 0.924466 | 0.153893 | 0.525276 | 0.022* | |
S3 | 0.56331 (2) | −0.62644 (5) | 0.31552 (2) | 0.01425 (10) | |
S4 | 0.52677 (2) | −0.58191 (5) | 0.51548 (2) | 0.01467 (10) | |
N3 | 0.50211 (7) | −0.1021 (2) | 0.34052 (9) | 0.0206 (4) | |
N4 | 0.51279 (7) | −0.0590 (2) | 0.58866 (9) | 0.0195 (4) | |
C35 | 0.65751 (7) | −0.6888 (2) | 0.42825 (9) | 0.0124 (4) | |
C36 | 0.69795 (7) | −0.7413 (2) | 0.40124 (9) | 0.0131 (4) | |
C37 | 0.71845 (8) | −0.6586 (2) | 0.36153 (10) | 0.0186 (4) | |
H37 | 0.707633 | −0.568364 | 0.354164 | 0.022* | |
C38 | 0.75448 (8) | −0.7076 (3) | 0.33286 (10) | 0.0215 (5) | |
H38 | 0.768718 | −0.649972 | 0.306776 | 0.026* | |
C39 | 0.76965 (7) | −0.8404 (3) | 0.34225 (10) | 0.0205 (5) | |
H39 | 0.793501 | −0.875084 | 0.321471 | 0.025* | |
C40 | 0.75015 (7) | −0.9225 (2) | 0.38183 (10) | 0.0195 (4) | |
H40 | 0.760911 | −1.013075 | 0.388597 | 0.023* | |
C41 | 0.71472 (7) | −0.8726 (2) | 0.41182 (9) | 0.0150 (4) | |
H41 | 0.701934 | −0.928464 | 0.439651 | 0.018* | |
C42 | 0.62263 (7) | −0.6412 (2) | 0.38994 (9) | 0.0119 (4) | |
C43 | 0.60479 (7) | −0.5061 (2) | 0.39284 (9) | 0.0131 (4) | |
H43 | 0.614614 | −0.438632 | 0.418425 | 0.016* | |
C44 | 0.57219 (7) | −0.4812 (2) | 0.35561 (9) | 0.0121 (4) | |
C45 | 0.60324 (7) | −0.7194 (2) | 0.34919 (8) | 0.0127 (4) | |
C46 | 0.61135 (8) | −0.8665 (2) | 0.33321 (10) | 0.0179 (4) | |
H46A | 0.583534 | −0.916143 | 0.331297 | 0.027* | |
H46B | 0.630187 | −0.910423 | 0.360710 | 0.027* | |
H46C | 0.625639 | −0.869350 | 0.297132 | 0.027* | |
C47 | 0.54704 (7) | −0.3538 (2) | 0.34963 (9) | 0.0132 (4) | |
C48 | 0.54585 (7) | −0.2589 (2) | 0.39318 (10) | 0.0154 (4) | |
H48 | 0.560452 | −0.278515 | 0.426778 | 0.019* | |
C49 | 0.52323 (8) | −0.1363 (2) | 0.38677 (10) | 0.0183 (4) | |
H49 | 0.522635 | −0.073131 | 0.416724 | 0.022* | |
C50 | 0.50267 (8) | −0.1932 (3) | 0.29910 (10) | 0.0217 (5) | |
H50 | 0.487755 | −0.170412 | 0.266032 | 0.026* | |
C51 | 0.52412 (7) | −0.3199 (2) | 0.30223 (9) | 0.0186 (4) | |
H51 | 0.523071 | −0.382631 | 0.272151 | 0.022* | |
C52 | 0.65133 (7) | −0.6757 (2) | 0.48315 (9) | 0.0136 (4) | |
C53 | 0.68559 (7) | −0.6962 (2) | 0.52585 (9) | 0.0156 (4) | |
C54 | 0.67439 (8) | −0.7577 (2) | 0.57610 (10) | 0.0209 (5) | |
H54 | 0.645722 | −0.792429 | 0.581358 | 0.025* | |
C55 | 0.70475 (10) | −0.7684 (3) | 0.61842 (11) | 0.0274 (6) | |
H55 | 0.696937 | −0.811501 | 0.652153 | 0.033* | |
C56 | 0.74651 (9) | −0.7159 (3) | 0.61127 (11) | 0.0285 (6) | |
H56 | 0.767015 | −0.720697 | 0.640519 | 0.034* | |
C57 | 0.75827 (8) | −0.6566 (3) | 0.56166 (12) | 0.0268 (6) | |
H57 | 0.787052 | −0.622512 | 0.556711 | 0.032* | |
C58 | 0.72815 (7) | −0.6466 (2) | 0.51880 (11) | 0.0206 (5) | |
H58 | 0.736508 | −0.606115 | 0.484762 | 0.025* | |
C59 | 0.60868 (7) | −0.6238 (2) | 0.50397 (8) | 0.0124 (4) | |
C60 | 0.60408 (7) | −0.4899 (2) | 0.52820 (9) | 0.0132 (4) | |
H60 | 0.628196 | −0.433435 | 0.538027 | 0.016* | |
C61 | 0.56173 (7) | −0.4509 (2) | 0.53587 (9) | 0.0133 (4) | |
H1 | 0.4224 (9) | −0.066 (2) | 0.6974 (11) | 0.016* | |
H5A | 0.4139 (9) | −0.100 (2) | 0.4414 (12) | 0.016* | |
C62 | 0.56924 (7) | −0.6876 (2) | 0.49598 (9) | 0.0134 (4) | |
C63 | 0.55977 (8) | −0.8281 (2) | 0.47279 (10) | 0.0186 (4) | |
H63A | 0.545232 | −0.884639 | 0.500792 | 0.028* | |
H63B | 0.587138 | −0.872515 | 0.461836 | 0.028* | |
H63C | 0.540738 | −0.818864 | 0.440587 | 0.028* | |
C64 | 0.54454 (7) | −0.3176 (2) | 0.55485 (9) | 0.0130 (4) | |
C65 | 0.57048 (7) | −0.2262 (2) | 0.58573 (9) | 0.0162 (4) | |
H65 | 0.599385 | −0.250978 | 0.595712 | 0.019* | |
C66 | 0.55344 (8) | −0.0998 (2) | 0.60141 (10) | 0.0196 (4) | |
H66 | 0.571315 | −0.038800 | 0.622175 | 0.024* | |
C67 | 0.48805 (8) | −0.1469 (2) | 0.55973 (10) | 0.0194 (4) | |
H67 | 0.459129 | −0.119665 | 0.550857 | 0.023* | |
C68 | 0.50226 (7) | −0.2752 (2) | 0.54203 (9) | 0.0165 (4) | |
H68 | 0.483476 | −0.333644 | 0.521412 | 0.020* | |
O1 | 0.42684 (6) | −0.14814 (18) | 0.68867 (8) | 0.0245 (4) | |
O2 | 0.49097 (6) | −0.10773 (19) | 0.72974 (8) | 0.0298 (4) | |
O3 | 0.48516 (6) | −0.81129 (17) | 0.61804 (8) | 0.0217 (3) | |
O4 | 0.55357 (6) | −0.7784 (2) | 0.64753 (10) | 0.0318 (5) | |
C69 | 0.47882 (7) | −0.3264 (2) | 0.68692 (9) | 0.0142 (4) | |
C70 | 0.44885 (7) | −0.4129 (2) | 0.66074 (9) | 0.0163 (4) | |
H70 | 0.420261 | −0.380456 | 0.653023 | 0.020* | |
C71 | 0.46080 (7) | −0.5464 (2) | 0.64599 (9) | 0.0158 (4) | |
H71 | 0.440283 | −0.605235 | 0.628400 | 0.019* | |
C72 | 0.50264 (7) | −0.5942 (2) | 0.65683 (9) | 0.0148 (4) | |
C73 | 0.53254 (7) | −0.5075 (2) | 0.68283 (10) | 0.0184 (4) | |
H73 | 0.561228 | −0.539541 | 0.690198 | 0.022* | |
C74 | 0.52056 (7) | −0.3745 (2) | 0.69799 (10) | 0.0174 (4) | |
H74 | 0.540979 | −0.316113 | 0.716012 | 0.021* | |
C75 | 0.46670 (8) | −0.1825 (2) | 0.70418 (9) | 0.0170 (4) | |
C76 | 0.51661 (8) | −0.7369 (2) | 0.64045 (10) | 0.0177 (4) | |
O5 | 0.42313 (6) | −0.18035 (18) | 0.43155 (8) | 0.0252 (4) | |
O6 | 0.35541 (7) | −0.2063 (2) | 0.39963 (12) | 0.0519 (7) | |
O7 | 0.47593 (6) | −0.84965 (18) | 0.35910 (8) | 0.0227 (4) | |
H7A | 0.4800 (15) | −0.928 (3) | 0.3418 (18) | 0.083 (15)* | |
H3A | 0.4972 (16) | −0.887 (4) | 0.610 (2) | 0.099* | |
O8 | 0.41260 (7) | −0.8770 (2) | 0.31555 (11) | 0.0436 (6) | |
C77 | 0.40522 (8) | −0.3937 (2) | 0.38991 (10) | 0.0185 (4) | |
C78 | 0.44613 (7) | −0.4457 (2) | 0.40265 (10) | 0.0172 (4) | |
H78 | 0.466505 | −0.389880 | 0.421986 | 0.021* | |
C79 | 0.45736 (7) | −0.5795 (2) | 0.38718 (10) | 0.0172 (4) | |
H79 | 0.485380 | −0.614985 | 0.395988 | 0.021* | |
C80 | 0.42765 (8) | −0.6612 (2) | 0.35886 (9) | 0.0173 (4) | |
C81 | 0.38661 (8) | −0.6089 (3) | 0.34627 (11) | 0.0246 (5) | |
H81 | 0.366228 | −0.664607 | 0.326904 | 0.029* | |
C82 | 0.37535 (8) | −0.4759 (3) | 0.36186 (11) | 0.0253 (5) | |
H82 | 0.347220 | −0.440700 | 0.353391 | 0.030* | |
C83 | 0.39161 (8) | −0.2508 (3) | 0.40720 (11) | 0.0243 (5) | |
C84 | 0.43781 (8) | −0.8066 (2) | 0.34184 (10) | 0.0203 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0190 (2) | 0.0150 (2) | 0.0153 (2) | −0.00409 (19) | −0.0061 (2) | 0.0040 (2) |
S2 | 0.0129 (2) | 0.0151 (2) | 0.0205 (3) | −0.00070 (19) | 0.00060 (19) | 0.0034 (2) |
N1 | 0.0195 (9) | 0.0124 (9) | 0.0296 (11) | −0.0014 (7) | −0.0045 (8) | −0.0011 (8) |
N2 | 0.0239 (10) | 0.0150 (9) | 0.0284 (11) | −0.0026 (8) | 0.0089 (8) | 0.0000 (8) |
C1 | 0.0141 (9) | 0.0101 (9) | 0.0175 (10) | −0.0016 (7) | −0.0015 (8) | 0.0004 (8) |
C2 | 0.0123 (9) | 0.0135 (9) | 0.0143 (9) | −0.0005 (7) | −0.0016 (7) | 0.0021 (7) |
C3 | 0.0205 (11) | 0.0162 (10) | 0.0174 (10) | −0.0041 (8) | −0.0011 (8) | −0.0014 (8) |
C4 | 0.0195 (11) | 0.0263 (12) | 0.0163 (10) | 0.0000 (9) | 0.0025 (9) | −0.0034 (9) |
C5 | 0.0142 (10) | 0.0243 (11) | 0.0198 (11) | −0.0063 (8) | 0.0011 (8) | 0.0027 (9) |
C6 | 0.0156 (10) | 0.0177 (10) | 0.0202 (11) | −0.0046 (8) | −0.0024 (8) | 0.0004 (9) |
C7 | 0.0129 (9) | 0.0145 (9) | 0.0161 (10) | −0.0013 (7) | −0.0012 (7) | −0.0013 (8) |
C8 | 0.0143 (9) | 0.0133 (9) | 0.0136 (9) | −0.0023 (7) | −0.0015 (7) | 0.0006 (7) |
C9 | 0.0151 (9) | 0.0137 (9) | 0.0138 (9) | −0.0016 (7) | −0.0025 (8) | 0.0007 (7) |
C10 | 0.0143 (9) | 0.0105 (9) | 0.0162 (10) | −0.0019 (7) | −0.0019 (8) | 0.0015 (8) |
C11 | 0.0161 (10) | 0.0147 (10) | 0.0153 (10) | −0.0033 (8) | −0.0029 (8) | 0.0006 (8) |
C12 | 0.0275 (12) | 0.0152 (10) | 0.0209 (11) | −0.0054 (9) | −0.0033 (9) | 0.0052 (9) |
C13 | 0.0134 (9) | 0.0122 (9) | 0.0164 (10) | −0.0004 (7) | −0.0013 (8) | 0.0017 (8) |
C14 | 0.0159 (10) | 0.0151 (10) | 0.0189 (10) | −0.0015 (8) | −0.0019 (8) | 0.0005 (8) |
C15 | 0.0189 (11) | 0.0131 (10) | 0.0265 (12) | 0.0002 (8) | 0.0017 (9) | 0.0037 (9) |
C16 | 0.0255 (12) | 0.0152 (10) | 0.0233 (11) | −0.0035 (9) | −0.0081 (9) | −0.0011 (8) |
C17 | 0.0241 (11) | 0.0159 (10) | 0.0179 (10) | −0.0039 (9) | −0.0051 (9) | 0.0007 (8) |
C18 | 0.0130 (9) | 0.0109 (9) | 0.0157 (10) | −0.0013 (7) | −0.0013 (7) | 0.0005 (7) |
C19 | 0.0168 (10) | 0.0125 (9) | 0.0159 (9) | −0.0060 (7) | −0.0029 (8) | 0.0035 (8) |
C20 | 0.0217 (11) | 0.0186 (10) | 0.0189 (11) | −0.0055 (9) | −0.0012 (9) | −0.0009 (8) |
C21 | 0.0350 (14) | 0.0216 (12) | 0.0168 (11) | −0.0118 (10) | −0.0051 (10) | −0.0007 (9) |
C22 | 0.0281 (13) | 0.0222 (11) | 0.0227 (12) | −0.0133 (10) | −0.0117 (10) | 0.0074 (9) |
C23 | 0.0169 (10) | 0.0203 (11) | 0.0285 (12) | −0.0045 (9) | −0.0080 (9) | 0.0099 (9) |
C24 | 0.0177 (10) | 0.0162 (10) | 0.0186 (11) | −0.0030 (8) | −0.0030 (8) | 0.0043 (8) |
C25 | 0.0151 (9) | 0.0131 (9) | 0.0125 (9) | −0.0037 (7) | −0.0012 (7) | 0.0010 (7) |
C26 | 0.0163 (10) | 0.0141 (9) | 0.0126 (9) | −0.0008 (7) | −0.0013 (8) | 0.0012 (8) |
C27 | 0.0171 (10) | 0.0119 (9) | 0.0133 (9) | −0.0010 (7) | 0.0006 (8) | 0.0016 (7) |
C28 | 0.0170 (10) | 0.0135 (9) | 0.0155 (10) | −0.0024 (8) | 0.0004 (8) | 0.0017 (8) |
C29 | 0.0204 (11) | 0.0146 (10) | 0.0258 (12) | −0.0001 (8) | 0.0015 (9) | 0.0028 (9) |
C30 | 0.0180 (10) | 0.0143 (10) | 0.0139 (10) | −0.0016 (8) | 0.0032 (8) | 0.0008 (8) |
C31 | 0.0196 (11) | 0.0166 (10) | 0.0218 (11) | −0.0012 (8) | 0.0024 (9) | 0.0030 (9) |
C32 | 0.0249 (12) | 0.0149 (10) | 0.0272 (12) | 0.0011 (9) | 0.0034 (10) | 0.0041 (9) |
C33 | 0.0178 (11) | 0.0183 (11) | 0.0282 (13) | −0.0044 (8) | 0.0049 (9) | −0.0015 (9) |
C34 | 0.0182 (10) | 0.0169 (10) | 0.0207 (11) | −0.0031 (8) | 0.0026 (8) | 0.0013 (8) |
S3 | 0.0160 (2) | 0.0138 (2) | 0.0129 (2) | 0.00273 (18) | −0.00244 (19) | −0.00271 (19) |
S4 | 0.0125 (2) | 0.0132 (2) | 0.0183 (2) | −0.00053 (18) | 0.00216 (19) | −0.00321 (19) |
N3 | 0.0209 (9) | 0.0157 (9) | 0.0252 (10) | 0.0035 (7) | 0.0010 (8) | 0.0001 (8) |
N4 | 0.0242 (10) | 0.0119 (8) | 0.0224 (10) | 0.0023 (7) | 0.0066 (8) | −0.0001 (7) |
C35 | 0.0122 (9) | 0.0085 (8) | 0.0165 (10) | 0.0013 (7) | −0.0008 (7) | 0.0002 (7) |
C36 | 0.0114 (9) | 0.0135 (9) | 0.0144 (9) | 0.0023 (7) | −0.0020 (7) | −0.0008 (7) |
C37 | 0.0208 (11) | 0.0153 (10) | 0.0197 (10) | 0.0023 (8) | 0.0008 (9) | 0.0042 (8) |
C38 | 0.0186 (11) | 0.0265 (12) | 0.0193 (11) | 0.0002 (9) | 0.0038 (9) | 0.0049 (9) |
C39 | 0.0131 (10) | 0.0296 (12) | 0.0188 (11) | 0.0045 (9) | 0.0008 (8) | −0.0015 (9) |
C40 | 0.0161 (10) | 0.0185 (10) | 0.0239 (11) | 0.0066 (8) | 0.0004 (9) | −0.0004 (9) |
C41 | 0.0162 (10) | 0.0134 (10) | 0.0154 (10) | 0.0004 (8) | 0.0007 (8) | 0.0007 (8) |
C42 | 0.0122 (9) | 0.0114 (9) | 0.0123 (9) | 0.0014 (7) | 0.0001 (7) | 0.0009 (7) |
C43 | 0.0143 (9) | 0.0119 (9) | 0.0131 (9) | −0.0001 (7) | 0.0007 (7) | −0.0013 (7) |
C44 | 0.0140 (9) | 0.0113 (9) | 0.0108 (9) | 0.0008 (7) | 0.0015 (7) | −0.0011 (7) |
C45 | 0.0142 (9) | 0.0123 (9) | 0.0115 (9) | 0.0021 (7) | −0.0001 (7) | −0.0004 (7) |
C46 | 0.0207 (11) | 0.0136 (10) | 0.0193 (11) | 0.0027 (8) | 0.0001 (9) | −0.0026 (8) |
C47 | 0.0127 (9) | 0.0113 (9) | 0.0156 (10) | 0.0009 (7) | 0.0008 (7) | 0.0023 (7) |
C48 | 0.0161 (10) | 0.0144 (10) | 0.0158 (10) | 0.0000 (8) | −0.0002 (8) | −0.0002 (8) |
C49 | 0.0212 (11) | 0.0131 (10) | 0.0206 (11) | 0.0012 (8) | 0.0014 (9) | −0.0023 (8) |
C50 | 0.0227 (11) | 0.0223 (11) | 0.0203 (11) | 0.0070 (9) | −0.0026 (9) | 0.0028 (9) |
C51 | 0.0211 (11) | 0.0197 (11) | 0.0151 (10) | 0.0071 (8) | −0.0018 (8) | −0.0019 (8) |
C52 | 0.0136 (9) | 0.0107 (9) | 0.0164 (10) | 0.0021 (7) | −0.0019 (8) | 0.0005 (7) |
C53 | 0.0173 (10) | 0.0133 (9) | 0.0162 (10) | 0.0057 (7) | −0.0039 (8) | −0.0030 (8) |
C54 | 0.0261 (12) | 0.0176 (11) | 0.0191 (11) | 0.0048 (9) | −0.0039 (9) | −0.0010 (8) |
C55 | 0.0394 (15) | 0.0236 (12) | 0.0192 (12) | 0.0108 (11) | −0.0088 (11) | 0.0002 (9) |
C56 | 0.0311 (14) | 0.0257 (12) | 0.0289 (13) | 0.0155 (11) | −0.0161 (11) | −0.0093 (10) |
C57 | 0.0183 (11) | 0.0273 (13) | 0.0349 (14) | 0.0088 (9) | −0.0085 (10) | −0.0158 (11) |
C58 | 0.0165 (10) | 0.0214 (11) | 0.0240 (11) | 0.0041 (8) | −0.0040 (9) | −0.0088 (9) |
C59 | 0.0148 (9) | 0.0126 (9) | 0.0097 (9) | 0.0022 (7) | −0.0007 (7) | 0.0000 (7) |
C60 | 0.0151 (9) | 0.0123 (9) | 0.0123 (9) | 0.0013 (7) | −0.0011 (7) | −0.0016 (7) |
C61 | 0.0156 (9) | 0.0119 (9) | 0.0124 (9) | 0.0016 (7) | 0.0002 (8) | −0.0020 (8) |
C62 | 0.0151 (10) | 0.0120 (9) | 0.0131 (9) | 0.0028 (8) | 0.0014 (8) | −0.0006 (7) |
C63 | 0.0219 (11) | 0.0112 (9) | 0.0228 (11) | −0.0018 (8) | 0.0025 (9) | −0.0034 (8) |
C64 | 0.0155 (10) | 0.0112 (9) | 0.0123 (9) | 0.0012 (7) | 0.0033 (7) | 0.0017 (7) |
C65 | 0.0174 (10) | 0.0157 (10) | 0.0155 (10) | 0.0011 (8) | 0.0012 (8) | −0.0019 (8) |
C66 | 0.0227 (11) | 0.0142 (10) | 0.0219 (11) | −0.0010 (8) | 0.0028 (9) | −0.0035 (9) |
C67 | 0.0200 (11) | 0.0157 (10) | 0.0226 (11) | 0.0054 (8) | 0.0048 (9) | 0.0000 (9) |
C68 | 0.0159 (10) | 0.0151 (10) | 0.0184 (11) | 0.0008 (8) | 0.0015 (8) | −0.0015 (8) |
O1 | 0.0238 (9) | 0.0134 (8) | 0.0362 (10) | 0.0058 (7) | −0.0029 (8) | −0.0066 (7) |
O2 | 0.0352 (10) | 0.0193 (8) | 0.0348 (11) | 0.0064 (7) | −0.0113 (9) | −0.0108 (8) |
O3 | 0.0205 (8) | 0.0121 (7) | 0.0324 (9) | 0.0014 (6) | 0.0022 (7) | −0.0054 (7) |
O4 | 0.0221 (9) | 0.0210 (9) | 0.0523 (13) | 0.0071 (7) | −0.0050 (9) | −0.0090 (9) |
C69 | 0.0188 (10) | 0.0119 (9) | 0.0118 (9) | 0.0005 (8) | 0.0020 (8) | −0.0007 (7) |
C70 | 0.0163 (10) | 0.0148 (10) | 0.0179 (10) | 0.0022 (8) | 0.0018 (8) | −0.0019 (8) |
C71 | 0.0159 (10) | 0.0137 (9) | 0.0177 (10) | −0.0014 (8) | 0.0013 (8) | −0.0036 (8) |
C72 | 0.0148 (9) | 0.0122 (9) | 0.0173 (10) | 0.0011 (7) | 0.0034 (8) | 0.0006 (8) |
C73 | 0.0143 (10) | 0.0159 (10) | 0.0250 (12) | 0.0017 (8) | 0.0003 (9) | −0.0019 (9) |
C74 | 0.0184 (10) | 0.0141 (10) | 0.0197 (11) | −0.0012 (8) | −0.0006 (8) | −0.0026 (8) |
C75 | 0.0243 (11) | 0.0144 (10) | 0.0122 (10) | 0.0030 (8) | 0.0018 (8) | 0.0007 (8) |
C76 | 0.0186 (10) | 0.0138 (10) | 0.0208 (11) | 0.0014 (8) | 0.0025 (9) | −0.0009 (8) |
O5 | 0.0210 (9) | 0.0130 (8) | 0.0415 (11) | 0.0006 (6) | 0.0055 (8) | −0.0076 (7) |
O6 | 0.0362 (12) | 0.0344 (12) | 0.0850 (19) | 0.0214 (10) | −0.0236 (12) | −0.0279 (12) |
O7 | 0.0208 (8) | 0.0173 (8) | 0.0300 (9) | 0.0049 (7) | −0.0040 (7) | −0.0029 (7) |
O8 | 0.0422 (12) | 0.0286 (10) | 0.0600 (14) | 0.0130 (9) | −0.0293 (11) | −0.0241 (10) |
C77 | 0.0183 (10) | 0.0177 (10) | 0.0196 (11) | 0.0037 (8) | 0.0005 (9) | −0.0027 (9) |
C78 | 0.0145 (10) | 0.0162 (10) | 0.0209 (11) | −0.0008 (8) | 0.0020 (8) | −0.0027 (8) |
C79 | 0.0126 (9) | 0.0165 (10) | 0.0226 (11) | 0.0025 (8) | 0.0015 (8) | −0.0012 (8) |
C80 | 0.0216 (11) | 0.0142 (10) | 0.0162 (10) | 0.0049 (8) | 0.0021 (8) | −0.0012 (8) |
C81 | 0.0234 (12) | 0.0243 (12) | 0.0260 (13) | 0.0039 (9) | −0.0068 (10) | −0.0075 (10) |
C82 | 0.0207 (11) | 0.0248 (12) | 0.0306 (13) | 0.0074 (9) | −0.0094 (10) | −0.0065 (10) |
C83 | 0.0227 (12) | 0.0205 (12) | 0.0296 (13) | 0.0070 (9) | 0.0001 (10) | −0.0063 (10) |
C84 | 0.0222 (11) | 0.0186 (11) | 0.0200 (11) | 0.0052 (9) | −0.0043 (9) | −0.0041 (9) |
S1—C10 | 1.724 (2) | C39—C40 | 1.383 (3) |
S1—C11 | 1.728 (2) | C40—H40 | 0.9500 |
S2—C27 | 1.731 (2) | C40—C41 | 1.394 (3) |
S2—C28 | 1.721 (2) | C41—H41 | 0.9500 |
N1—C15 | 1.335 (3) | C42—C43 | 1.418 (3) |
N1—C16 | 1.342 (3) | C42—C45 | 1.380 (3) |
N2—C32 | 1.343 (3) | C43—H43 | 0.9500 |
N2—C33 | 1.330 (3) | C43—C44 | 1.369 (3) |
C1—C2 | 1.493 (3) | C44—C47 | 1.460 (3) |
C1—C8 | 1.488 (3) | C45—C46 | 1.495 (3) |
C1—C18 | 1.358 (3) | C46—H46A | 0.9800 |
C2—C3 | 1.396 (3) | C46—H46B | 0.9800 |
C2—C7 | 1.400 (3) | C46—H46C | 0.9800 |
C3—H3 | 0.9500 | C47—C48 | 1.401 (3) |
C3—C4 | 1.388 (3) | C47—C51 | 1.388 (3) |
C4—H4 | 0.9500 | C48—H48 | 0.9500 |
C4—C5 | 1.388 (3) | C48—C49 | 1.382 (3) |
C5—H5 | 0.9500 | C49—H49 | 0.9500 |
C5—C6 | 1.385 (3) | C50—H50 | 0.9500 |
C6—H6 | 0.9500 | C50—C51 | 1.393 (3) |
C6—C7 | 1.394 (3) | C51—H51 | 0.9500 |
C7—H7 | 0.9500 | C52—C53 | 1.490 (3) |
C8—C9 | 1.422 (3) | C52—C59 | 1.489 (3) |
C8—C11 | 1.374 (3) | C53—C54 | 1.400 (3) |
C9—H9 | 0.9500 | C53—C58 | 1.401 (3) |
C9—C10 | 1.361 (3) | C54—H54 | 0.9500 |
C10—C13 | 1.461 (3) | C54—C55 | 1.391 (3) |
C11—C12 | 1.501 (3) | C55—H55 | 0.9500 |
C12—H12A | 0.9800 | C55—C56 | 1.389 (4) |
C12—H12B | 0.9800 | C56—H56 | 0.9500 |
C12—H12C | 0.9800 | C56—C57 | 1.382 (4) |
C13—C14 | 1.404 (3) | C57—H57 | 0.9500 |
C13—C17 | 1.396 (3) | C57—C58 | 1.395 (3) |
C14—H14 | 0.9500 | C58—H58 | 0.9500 |
C14—C15 | 1.381 (3) | C59—C60 | 1.429 (3) |
C15—H15 | 0.9500 | C59—C62 | 1.372 (3) |
C16—H16 | 0.9500 | C60—H60 | 0.9500 |
C16—C17 | 1.392 (3) | C60—C61 | 1.365 (3) |
C17—H17 | 0.9500 | C61—C64 | 1.467 (3) |
C18—C19 | 1.488 (3) | C62—C63 | 1.498 (3) |
C18—C25 | 1.486 (3) | C63—H63A | 0.9800 |
C19—C20 | 1.404 (3) | C63—H63B | 0.9800 |
C19—C24 | 1.400 (3) | C63—H63C | 0.9800 |
C20—H20 | 0.9500 | C64—C65 | 1.406 (3) |
C20—C21 | 1.387 (3) | C64—C68 | 1.396 (3) |
C21—H21 | 0.9500 | C65—H65 | 0.9500 |
C21—C22 | 1.392 (4) | C65—C66 | 1.383 (3) |
C22—H22 | 0.9500 | C66—H66 | 0.9500 |
C22—C23 | 1.385 (4) | C67—H67 | 0.9500 |
C23—H23 | 0.9500 | C67—C68 | 1.383 (3) |
C23—C24 | 1.392 (3) | C68—H68 | 0.9500 |
C24—H24 | 0.9500 | O1—H1 | 0.83 (2) |
C25—C26 | 1.434 (3) | O1—C75 | 1.322 (3) |
C25—C28 | 1.372 (3) | O2—C75 | 1.209 (3) |
C26—H26 | 0.9500 | O3—C76 | 1.321 (3) |
C26—C27 | 1.370 (3) | O3—H3A | 0.84 (3) |
C27—C30 | 1.459 (3) | O4—C76 | 1.215 (3) |
C28—C29 | 1.499 (3) | C69—C70 | 1.396 (3) |
C29—H29A | 0.9800 | C69—C74 | 1.388 (3) |
C29—H29B | 0.9800 | C69—C75 | 1.500 (3) |
C29—H29C | 0.9800 | C70—H70 | 0.9500 |
C30—C31 | 1.395 (3) | C70—C71 | 1.388 (3) |
C30—C34 | 1.402 (3) | C71—H71 | 0.9500 |
C31—H31 | 0.9500 | C71—C72 | 1.389 (3) |
C31—C32 | 1.390 (3) | C72—C73 | 1.394 (3) |
C32—H32 | 0.9500 | C72—C76 | 1.499 (3) |
C33—H33 | 0.9500 | C73—H73 | 0.9500 |
C33—C34 | 1.385 (3) | C73—C74 | 1.387 (3) |
C34—H34 | 0.9500 | C74—H74 | 0.9500 |
S3—C44 | 1.731 (2) | O5—H5A | 0.86 (2) |
S3—C45 | 1.725 (2) | O5—C83 | 1.322 (3) |
S4—C61 | 1.732 (2) | O6—C83 | 1.205 (3) |
S4—C62 | 1.722 (2) | O7—H7A | 0.88 (2) |
N3—C49 | 1.338 (3) | O7—C84 | 1.310 (3) |
N3—C50 | 1.337 (3) | O8—C84 | 1.212 (3) |
N4—C66 | 1.344 (3) | C77—C78 | 1.387 (3) |
N4—C67 | 1.339 (3) | C77—C82 | 1.391 (3) |
C35—C36 | 1.492 (3) | C77—C83 | 1.503 (3) |
C35—C42 | 1.491 (3) | C78—H78 | 0.9500 |
C35—C52 | 1.353 (3) | C78—C79 | 1.390 (3) |
C36—C37 | 1.402 (3) | C79—H79 | 0.9500 |
C36—C41 | 1.394 (3) | C79—C80 | 1.388 (3) |
C37—H37 | 0.9500 | C80—C81 | 1.391 (3) |
C37—C38 | 1.390 (3) | C80—C84 | 1.499 (3) |
C38—H38 | 0.9500 | C81—H81 | 0.9500 |
C38—C39 | 1.384 (3) | C81—C82 | 1.384 (3) |
C39—H39 | 0.9500 | C82—H82 | 0.9500 |
C10—S1—C11 | 92.46 (10) | C45—C42—C35 | 125.98 (19) |
C28—S2—C27 | 92.64 (11) | C45—C42—C43 | 111.97 (19) |
C15—N1—C16 | 117.2 (2) | C42—C43—H43 | 122.9 |
C33—N2—C32 | 117.7 (2) | C44—C43—C42 | 114.29 (19) |
C8—C1—C2 | 113.47 (18) | C44—C43—H43 | 122.9 |
C18—C1—C2 | 126.6 (2) | C43—C44—S3 | 110.08 (16) |
C18—C1—C8 | 119.84 (19) | C43—C44—C47 | 126.9 (2) |
C3—C2—C1 | 118.59 (19) | C47—C44—S3 | 123.04 (16) |
C3—C2—C7 | 119.0 (2) | C42—C45—S3 | 111.10 (15) |
C7—C2—C1 | 122.16 (19) | C42—C45—C46 | 129.5 (2) |
C2—C3—H3 | 119.6 | C46—C45—S3 | 119.39 (16) |
C4—C3—C2 | 120.7 (2) | C45—C46—H46A | 109.5 |
C4—C3—H3 | 119.6 | C45—C46—H46B | 109.5 |
C3—C4—H4 | 120.1 | C45—C46—H46C | 109.5 |
C3—C4—C5 | 119.8 (2) | H46A—C46—H46B | 109.5 |
C5—C4—H4 | 120.1 | H46A—C46—H46C | 109.5 |
C4—C5—H5 | 120.0 | H46B—C46—H46C | 109.5 |
C6—C5—C4 | 120.1 (2) | C48—C47—C44 | 119.43 (19) |
C6—C5—H5 | 120.0 | C51—C47—C44 | 123.3 (2) |
C5—C6—H6 | 119.8 | C51—C47—C48 | 117.2 (2) |
C5—C6—C7 | 120.3 (2) | C47—C48—H48 | 120.3 |
C7—C6—H6 | 119.8 | C49—C48—C47 | 119.4 (2) |
C2—C7—H7 | 120.0 | C49—C48—H48 | 120.3 |
C6—C7—C2 | 119.9 (2) | N3—C49—C48 | 123.3 (2) |
C6—C7—H7 | 120.0 | N3—C49—H49 | 118.3 |
C9—C8—C1 | 121.76 (19) | C48—C49—H49 | 118.3 |
C11—C8—C1 | 126.17 (19) | N3—C50—H50 | 118.5 |
C11—C8—C9 | 112.03 (19) | N3—C50—C51 | 123.0 (2) |
C8—C9—H9 | 123.0 | C51—C50—H50 | 118.5 |
C10—C9—C8 | 114.05 (19) | C47—C51—C50 | 119.5 (2) |
C10—C9—H9 | 123.0 | C47—C51—H51 | 120.2 |
C9—C10—S1 | 110.49 (16) | C50—C51—H51 | 120.2 |
C9—C10—C13 | 125.6 (2) | C35—C52—C53 | 125.1 (2) |
C13—C10—S1 | 123.89 (16) | C35—C52—C59 | 119.30 (19) |
C8—C11—S1 | 110.97 (16) | C59—C52—C53 | 115.35 (18) |
C8—C11—C12 | 128.9 (2) | C54—C53—C52 | 119.4 (2) |
C12—C11—S1 | 120.05 (17) | C54—C53—C58 | 118.7 (2) |
C11—C12—H12A | 109.5 | C58—C53—C52 | 121.8 (2) |
C11—C12—H12B | 109.5 | C53—C54—H54 | 119.6 |
C11—C12—H12C | 109.5 | C55—C54—C53 | 120.8 (2) |
H12A—C12—H12B | 109.5 | C55—C54—H54 | 119.6 |
H12A—C12—H12C | 109.5 | C54—C55—H55 | 120.1 |
H12B—C12—H12C | 109.5 | C56—C55—C54 | 119.9 (3) |
C14—C13—C10 | 119.6 (2) | C56—C55—H55 | 120.1 |
C17—C13—C10 | 122.9 (2) | C55—C56—H56 | 120.0 |
C17—C13—C14 | 117.5 (2) | C57—C56—C55 | 120.1 (2) |
C13—C14—H14 | 120.5 | C57—C56—H56 | 120.0 |
C15—C14—C13 | 119.0 (2) | C56—C57—H57 | 119.8 |
C15—C14—H14 | 120.5 | C56—C57—C58 | 120.4 (3) |
N1—C15—C14 | 123.9 (2) | C58—C57—H57 | 119.8 |
N1—C15—H15 | 118.1 | C53—C58—H58 | 119.9 |
C14—C15—H15 | 118.1 | C57—C58—C53 | 120.1 (2) |
N1—C16—H16 | 118.3 | C57—C58—H58 | 119.9 |
N1—C16—C17 | 123.5 (2) | C60—C59—C52 | 122.09 (19) |
C17—C16—H16 | 118.3 | C62—C59—C52 | 125.13 (19) |
C13—C17—H17 | 120.5 | C62—C59—C60 | 112.24 (19) |
C16—C17—C13 | 118.9 (2) | C59—C60—H60 | 123.2 |
C16—C17—H17 | 120.5 | C61—C60—C59 | 113.60 (19) |
C1—C18—C19 | 125.8 (2) | C61—C60—H60 | 123.2 |
C1—C18—C25 | 118.50 (19) | C60—C61—S4 | 110.37 (15) |
C25—C18—C19 | 115.41 (18) | C60—C61—C64 | 128.9 (2) |
C20—C19—C18 | 119.5 (2) | C64—C61—S4 | 120.65 (16) |
C24—C19—C18 | 121.5 (2) | C59—C62—S4 | 111.18 (16) |
C24—C19—C20 | 118.6 (2) | C59—C62—C63 | 129.2 (2) |
C19—C20—H20 | 119.6 | C63—C62—S4 | 119.63 (16) |
C21—C20—C19 | 120.7 (2) | C62—C63—H63A | 109.5 |
C21—C20—H20 | 119.6 | C62—C63—H63B | 109.5 |
C20—C21—H21 | 120.0 | C62—C63—H63C | 109.5 |
C20—C21—C22 | 120.1 (2) | H63A—C63—H63B | 109.5 |
C22—C21—H21 | 120.0 | H63A—C63—H63C | 109.5 |
C21—C22—H22 | 120.1 | H63B—C63—H63C | 109.5 |
C23—C22—C21 | 119.8 (2) | C65—C64—C61 | 121.11 (19) |
C23—C22—H22 | 120.1 | C68—C64—C61 | 121.5 (2) |
C22—C23—H23 | 119.7 | C68—C64—C65 | 117.4 (2) |
C22—C23—C24 | 120.6 (2) | C64—C65—H65 | 120.4 |
C24—C23—H23 | 119.7 | C66—C65—C64 | 119.3 (2) |
C19—C24—H24 | 119.9 | C66—C65—H65 | 120.4 |
C23—C24—C19 | 120.2 (2) | N4—C66—C65 | 123.1 (2) |
C23—C24—H24 | 119.9 | N4—C66—H66 | 118.4 |
C26—C25—C18 | 121.91 (19) | C65—C66—H66 | 118.4 |
C28—C25—C18 | 125.28 (19) | N4—C67—H67 | 118.2 |
C28—C25—C26 | 112.20 (19) | N4—C67—C68 | 123.6 (2) |
C25—C26—H26 | 123.3 | C68—C67—H67 | 118.2 |
C27—C26—C25 | 113.35 (19) | C64—C68—H68 | 120.4 |
C27—C26—H26 | 123.3 | C67—C68—C64 | 119.2 (2) |
C26—C27—S2 | 110.41 (16) | C67—C68—H68 | 120.4 |
C26—C27—C30 | 128.5 (2) | C75—O1—H1 | 108.7 (19) |
C30—C27—S2 | 120.99 (16) | C76—O3—H3A | 104 (4) |
C25—C28—S2 | 111.29 (16) | C70—C69—C75 | 121.3 (2) |
C25—C28—C29 | 129.1 (2) | C74—C69—C70 | 119.7 (2) |
C29—C28—S2 | 119.55 (17) | C74—C69—C75 | 119.0 (2) |
C28—C29—H29A | 109.5 | C69—C70—H70 | 120.0 |
C28—C29—H29B | 109.5 | C71—C70—C69 | 120.0 (2) |
C28—C29—H29C | 109.5 | C71—C70—H70 | 120.0 |
H29A—C29—H29B | 109.5 | C70—C71—H71 | 119.9 |
H29A—C29—H29C | 109.5 | C70—C71—C72 | 120.3 (2) |
H29B—C29—H29C | 109.5 | C72—C71—H71 | 119.9 |
C31—C30—C27 | 121.4 (2) | C71—C72—C73 | 119.6 (2) |
C31—C30—C34 | 117.2 (2) | C71—C72—C76 | 121.4 (2) |
C34—C30—C27 | 121.4 (2) | C73—C72—C76 | 119.1 (2) |
C30—C31—H31 | 120.3 | C72—C73—H73 | 119.9 |
C32—C31—C30 | 119.3 (2) | C74—C73—C72 | 120.2 (2) |
C32—C31—H31 | 120.3 | C74—C73—H73 | 119.9 |
N2—C32—C31 | 123.1 (2) | C69—C74—H74 | 119.9 |
N2—C32—H32 | 118.5 | C73—C74—C69 | 120.2 (2) |
C31—C32—H32 | 118.5 | C73—C74—H74 | 119.9 |
N2—C33—H33 | 118.3 | O1—C75—C69 | 112.5 (2) |
N2—C33—C34 | 123.4 (2) | O2—C75—O1 | 124.4 (2) |
C34—C33—H33 | 118.3 | O2—C75—C69 | 123.1 (2) |
C30—C34—H34 | 120.3 | O3—C76—C72 | 113.69 (19) |
C33—C34—C30 | 119.3 (2) | O4—C76—O3 | 124.1 (2) |
C33—C34—H34 | 120.3 | O4—C76—C72 | 122.2 (2) |
C45—S3—C44 | 92.56 (10) | C83—O5—H5A | 110.5 (19) |
C62—S4—C61 | 92.53 (10) | C84—O7—H7A | 104 (3) |
C50—N3—C49 | 117.6 (2) | C78—C77—C82 | 119.9 (2) |
C67—N4—C66 | 117.5 (2) | C78—C77—C83 | 121.5 (2) |
C42—C35—C36 | 115.30 (18) | C82—C77—C83 | 118.6 (2) |
C52—C35—C36 | 125.57 (19) | C77—C78—H78 | 120.0 |
C52—C35—C42 | 119.05 (19) | C77—C78—C79 | 120.1 (2) |
C37—C36—C35 | 118.78 (19) | C79—C78—H78 | 120.0 |
C41—C36—C35 | 122.39 (19) | C78—C79—H79 | 120.0 |
C41—C36—C37 | 118.7 (2) | C80—C79—C78 | 120.0 (2) |
C36—C37—H37 | 119.8 | C80—C79—H79 | 120.0 |
C38—C37—C36 | 120.4 (2) | C79—C80—C81 | 119.7 (2) |
C38—C37—H37 | 119.8 | C79—C80—C84 | 122.3 (2) |
C37—C38—H38 | 120.0 | C81—C80—C84 | 118.0 (2) |
C39—C38—C37 | 120.1 (2) | C80—C81—H81 | 119.9 |
C39—C38—H38 | 120.0 | C82—C81—C80 | 120.2 (2) |
C38—C39—H39 | 119.9 | C82—C81—H81 | 119.9 |
C40—C39—C38 | 120.1 (2) | C77—C82—H82 | 120.0 |
C40—C39—H39 | 119.9 | C81—C82—C77 | 120.0 (2) |
C39—C40—H40 | 120.0 | C81—C82—H82 | 120.0 |
C39—C40—C41 | 120.1 (2) | O5—C83—C77 | 113.3 (2) |
C41—C40—H40 | 120.0 | O6—C83—O5 | 123.9 (2) |
C36—C41—C40 | 120.5 (2) | O6—C83—C77 | 122.8 (2) |
C36—C41—H41 | 119.8 | O7—C84—C80 | 113.3 (2) |
C40—C41—H41 | 119.8 | O8—C84—O7 | 124.0 (2) |
C43—C42—C35 | 122.04 (19) | O8—C84—C80 | 122.7 (2) |
S1—C10—C13—C14 | 153.33 (18) | C36—C35—C52—C59 | −178.90 (19) |
S1—C10—C13—C17 | −27.6 (3) | C36—C37—C38—C39 | 1.8 (4) |
S2—C27—C30—C31 | 163.93 (18) | C37—C36—C41—C40 | −2.5 (3) |
S2—C27—C30—C34 | −17.5 (3) | C37—C38—C39—C40 | −2.7 (4) |
N1—C16—C17—C13 | −0.2 (4) | C38—C39—C40—C41 | 1.0 (4) |
N2—C33—C34—C30 | −0.1 (4) | C39—C40—C41—C36 | 1.7 (4) |
C1—C2—C3—C4 | −173.0 (2) | C41—C36—C37—C38 | 0.8 (3) |
C1—C2—C7—C6 | 172.1 (2) | C42—C35—C36—C37 | 51.9 (3) |
C1—C8—C9—C10 | 177.7 (2) | C42—C35—C36—C41 | −124.5 (2) |
C1—C8—C11—S1 | −177.39 (18) | C42—C35—C52—C53 | −169.29 (19) |
C1—C8—C11—C12 | 5.3 (4) | C42—C35—C52—C59 | 4.5 (3) |
C1—C18—C19—C20 | −146.8 (2) | C42—C43—C44—S3 | −0.5 (2) |
C1—C18—C19—C24 | 39.8 (3) | C42—C43—C44—C47 | 178.4 (2) |
C1—C18—C25—C26 | −111.9 (2) | C43—C42—C45—S3 | −0.4 (2) |
C1—C18—C25—C28 | 58.5 (3) | C43—C42—C45—C46 | −178.4 (2) |
C2—C1—C8—C9 | −125.3 (2) | C43—C44—C47—C48 | −19.1 (3) |
C2—C1—C8—C11 | 52.3 (3) | C43—C44—C47—C51 | 160.3 (2) |
C2—C1—C18—C19 | 9.3 (4) | C44—S3—C45—C42 | 0.11 (17) |
C2—C1—C18—C25 | −177.48 (19) | C44—S3—C45—C46 | 178.34 (18) |
C2—C3—C4—C5 | 0.6 (4) | C44—C47—C48—C49 | 177.9 (2) |
C3—C2—C7—C6 | −2.1 (3) | C44—C47—C51—C50 | −177.0 (2) |
C3—C4—C5—C6 | −1.9 (4) | C45—S3—C44—C43 | 0.20 (17) |
C4—C5—C6—C7 | 1.2 (4) | C45—S3—C44—C47 | −178.71 (19) |
C5—C6—C7—C2 | 0.9 (3) | C45—C42—C43—C44 | 0.6 (3) |
C7—C2—C3—C4 | 1.4 (3) | C47—C48—C49—N3 | −0.2 (3) |
C8—C1—C2—C3 | 45.1 (3) | C48—C47—C51—C50 | 2.4 (3) |
C8—C1—C2—C7 | −129.1 (2) | C49—N3—C50—C51 | −0.2 (4) |
C8—C1—C18—C19 | −166.1 (2) | C50—N3—C49—C48 | 1.1 (4) |
C8—C1—C18—C25 | 7.0 (3) | C51—C47—C48—C49 | −1.5 (3) |
C8—C9—C10—S1 | −0.1 (2) | C52—C35—C36—C37 | −124.9 (2) |
C8—C9—C10—C13 | −179.6 (2) | C52—C35—C36—C41 | 58.8 (3) |
C9—C8—C11—S1 | 0.4 (2) | C52—C35—C42—C43 | 52.9 (3) |
C9—C8—C11—C12 | −176.9 (2) | C52—C35—C42—C45 | −125.7 (2) |
C9—C10—C13—C14 | −27.3 (3) | C52—C53—C54—C55 | −174.9 (2) |
C9—C10—C13—C17 | 151.9 (2) | C52—C53—C58—C57 | 174.1 (2) |
C10—S1—C11—C8 | −0.39 (18) | C52—C59—C60—C61 | 169.05 (19) |
C10—S1—C11—C12 | 177.2 (2) | C52—C59—C62—S4 | −169.36 (17) |
C10—C13—C14—C15 | 179.4 (2) | C52—C59—C62—C63 | 9.4 (4) |
C10—C13—C17—C16 | −179.0 (2) | C53—C52—C59—C60 | 65.0 (3) |
C11—S1—C10—C9 | 0.28 (18) | C53—C52—C59—C62 | −124.1 (2) |
C11—S1—C10—C13 | 179.8 (2) | C53—C54—C55—C56 | 1.0 (4) |
C11—C8—C9—C10 | −0.2 (3) | C54—C53—C58—C57 | −1.1 (3) |
C13—C14—C15—N1 | −0.7 (4) | C54—C55—C56—C57 | −1.8 (4) |
C14—C13—C17—C16 | 0.2 (3) | C55—C56—C57—C58 | 1.2 (4) |
C15—N1—C16—C17 | −0.3 (4) | C56—C57—C58—C53 | 0.2 (3) |
C16—N1—C15—C14 | 0.7 (3) | C58—C53—C54—C55 | 0.5 (3) |
C17—C13—C14—C15 | 0.2 (3) | C59—C52—C53—C54 | 42.7 (3) |
C18—C1—C2—C3 | −130.6 (2) | C59—C52—C53—C58 | −132.5 (2) |
C18—C1—C2—C7 | 55.2 (3) | C59—C60—C61—S4 | 2.1 (2) |
C18—C1—C8—C9 | 50.8 (3) | C59—C60—C61—C64 | −174.1 (2) |
C18—C1—C8—C11 | −131.6 (2) | C60—C59—C62—S4 | 2.3 (2) |
C18—C19—C20—C21 | −174.1 (2) | C60—C59—C62—C63 | −178.9 (2) |
C18—C19—C24—C23 | 173.7 (2) | C60—C61—C64—C65 | −22.4 (4) |
C18—C25—C26—C27 | 168.0 (2) | C60—C61—C64—C68 | 156.1 (2) |
C18—C25—C28—S2 | −168.48 (17) | C61—S4—C62—C59 | −0.98 (18) |
C18—C25—C28—C29 | 10.0 (4) | C61—S4—C62—C63 | −179.87 (19) |
C19—C18—C25—C26 | 62.0 (3) | C61—C64—C65—C66 | 178.1 (2) |
C19—C18—C25—C28 | −127.6 (2) | C61—C64—C68—C67 | −178.3 (2) |
C19—C20—C21—C22 | 1.0 (4) | C62—S4—C61—C60 | −0.67 (18) |
C20—C19—C24—C23 | 0.2 (3) | C62—S4—C61—C64 | 175.89 (19) |
C20—C21—C22—C23 | −1.2 (4) | C62—C59—C60—C61 | −2.9 (3) |
C21—C22—C23—C24 | 0.9 (4) | C64—C65—C66—N4 | 0.2 (4) |
C22—C23—C24—C19 | −0.4 (3) | C65—C64—C68—C67 | 0.3 (3) |
C24—C19—C20—C21 | −0.5 (3) | C66—N4—C67—C68 | −0.7 (4) |
C25—C18—C19—C20 | 39.8 (3) | C67—N4—C66—C65 | 0.5 (4) |
C25—C18—C19—C24 | −133.6 (2) | C68—C64—C65—C66 | −0.6 (3) |
C25—C26—C27—S2 | 2.7 (2) | C69—C70—C71—C72 | −0.4 (3) |
C25—C26—C27—C30 | −173.3 (2) | C70—C69—C74—C73 | 0.4 (3) |
C26—C25—C28—S2 | 2.7 (2) | C70—C69—C75—O1 | −4.0 (3) |
C26—C25—C28—C29 | −178.8 (2) | C70—C69—C75—O2 | 175.6 (2) |
C26—C27—C30—C31 | −20.5 (4) | C70—C71—C72—C73 | 0.2 (3) |
C26—C27—C30—C34 | 158.2 (2) | C70—C71—C72—C76 | −178.9 (2) |
C27—S2—C28—C25 | −1.02 (18) | C71—C72—C73—C74 | 0.3 (3) |
C27—S2—C28—C29 | −179.67 (19) | C71—C72—C76—O3 | −3.2 (3) |
C27—C30—C31—C32 | 177.8 (2) | C71—C72—C76—O4 | 176.9 (2) |
C27—C30—C34—C33 | −177.8 (2) | C72—C73—C74—C69 | −0.6 (4) |
C28—S2—C27—C26 | −1.00 (18) | C73—C72—C76—O3 | 177.6 (2) |
C28—S2—C27—C30 | 175.34 (18) | C73—C72—C76—O4 | −2.3 (4) |
C28—C25—C26—C27 | −3.6 (3) | C74—C69—C70—C71 | 0.1 (3) |
C30—C31—C32—N2 | 0.0 (4) | C74—C69—C75—O1 | 176.9 (2) |
C31—C30—C34—C33 | 0.9 (3) | C74—C69—C75—O2 | −3.6 (3) |
C32—N2—C33—C34 | −0.8 (4) | C75—C69—C70—C71 | −179.0 (2) |
C33—N2—C32—C31 | 0.9 (4) | C75—C69—C74—C73 | 179.6 (2) |
C34—C30—C31—C32 | −0.9 (3) | C76—C72—C73—C74 | 179.5 (2) |
S3—C44—C47—C48 | 159.66 (17) | C77—C78—C79—C80 | 0.1 (4) |
S3—C44—C47—C51 | −21.0 (3) | C78—C77—C82—C81 | −0.6 (4) |
S4—C61—C64—C65 | 161.69 (17) | C78—C77—C83—O5 | 4.3 (4) |
S4—C61—C64—C68 | −19.7 (3) | C78—C77—C83—O6 | −175.3 (3) |
N3—C50—C51—C47 | −1.6 (4) | C78—C79—C80—C81 | −0.3 (4) |
N4—C67—C68—C64 | 0.3 (4) | C78—C79—C80—C84 | −179.2 (2) |
C35—C36—C37—C38 | −175.7 (2) | C79—C80—C81—C82 | 0.0 (4) |
C35—C36—C41—C40 | 173.8 (2) | C79—C80—C84—O7 | 3.7 (3) |
C35—C42—C43—C44 | −178.19 (19) | C79—C80—C84—O8 | −177.5 (3) |
C35—C42—C45—S3 | 178.30 (17) | C80—C81—C82—C77 | 0.4 (4) |
C35—C42—C45—C46 | 0.3 (4) | C81—C80—C84—O7 | −175.2 (2) |
C35—C52—C53—C54 | −143.3 (2) | C81—C80—C84—O8 | 3.5 (4) |
C35—C52—C53—C58 | 41.5 (3) | C82—C77—C78—C79 | 0.3 (4) |
C35—C52—C59—C60 | −109.3 (2) | C82—C77—C83—O5 | −177.5 (2) |
C35—C52—C59—C62 | 61.6 (3) | C82—C77—C83—O6 | 2.9 (4) |
C36—C35—C42—C43 | −124.1 (2) | C83—C77—C78—C79 | 178.5 (2) |
C36—C35—C42—C45 | 57.4 (3) | C83—C77—C82—C81 | −178.8 (2) |
C36—C35—C52—C53 | 7.3 (3) | C84—C80—C81—C82 | 179.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.83 (2) | 1.85 (2) | 2.650 (3) | 161 (3) |
O5—H5A···N2i | 0.86 (2) | 1.77 (2) | 2.636 (3) | 178 (3) |
O7—H7A···N3ii | 0.88 (2) | 1.81 (3) | 2.609 (3) | 150 (5) |
O3—H3A···N4ii | 0.84 (3) | 1.81 (3) | 2.639 (2) | 169 (5) |
Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) x, y−1, z. |
C68H56CoN4O2S4 | Dx = 1.070 Mg m−3 |
Mr = 1148.33 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Fddd | Cell parameters from 9970 reflections |
a = 9.8404 (4) Å | θ = 2.3–26.2° |
b = 21.4458 (8) Å | µ = 0.40 mm−1 |
c = 67.537 (3) Å | T = 90 K |
V = 14252.6 (10) Å3 | Prism, colourless |
Z = 8 | 0.06 × 0.06 × 0.02 mm |
F(000) = 4792 |
Bruker APEX-II CCD diffractometer | 3390 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.047 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1167 before and 0.0596 after correction. The Ratio of minimum to maximum transmission is 0.8919. The λ/2 correction factor is Not present. | θmax = 28.3°, θmin = 2.0° |
Tmin = 0.665, Tmax = 0.746 | h = −13→13 |
29065 measured reflections | k = −28→27 |
4446 independent reflections | l = −90→54 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0341P)2 + 47.4853P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.003 |
4446 reflections | Δρmax = 0.58 e Å−3 |
182 parameters | Δρmin = −0.66 e Å−3 |
0 restraints |
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) | |
Co1 | 0.625000 | 0.125000 | 0.625000 | 0.0605 (3) | |
S1 | 0.55657 (5) | 0.38490 (3) | 0.55195 (2) | 0.03477 (14) | |
O1 | 0.8380 (3) | 0.125000 | 0.625000 | 0.0650 (8) | |
H1A | 0.902538 | 0.094114 | 0.618718 | 0.098* | 0.5 |
H1B | 0.902538 | 0.155936 | 0.631262 | 0.098* | 0.5 |
N1 | 0.6375 (3) | 0.19489 (9) | 0.60233 (2) | 0.0603 (7) | |
C1 | 0.80629 (19) | 0.37441 (8) | 0.50525 (2) | 0.0258 (4) | |
C2 | 0.7236 (2) | 0.37812 (9) | 0.48671 (2) | 0.0289 (4) | |
C3 | 0.6153 (2) | 0.33763 (10) | 0.48373 (3) | 0.0351 (5) | |
H3 | 0.594721 | 0.307101 | 0.493476 | 0.042* | |
C4 | 0.5364 (2) | 0.34124 (11) | 0.46663 (3) | 0.0437 (6) | |
H4 | 0.463848 | 0.312711 | 0.464656 | 0.052* | |
C5 | 0.5636 (2) | 0.38623 (11) | 0.45252 (3) | 0.0445 (6) | |
H5 | 0.509571 | 0.388892 | 0.440902 | 0.053* | |
C6 | 0.6694 (2) | 0.42713 (11) | 0.45541 (3) | 0.0407 (6) | |
H6 | 0.687939 | 0.458175 | 0.445752 | 0.049* | |
C7 | 0.7497 (2) | 0.42350 (10) | 0.47238 (3) | 0.0338 (5) | |
H7 | 0.822556 | 0.452012 | 0.474198 | 0.041* | |
C8 | 0.72822 (19) | 0.36796 (8) | 0.52400 (2) | 0.0252 (4) | |
C9 | 0.7548 (2) | 0.32146 (9) | 0.53852 (2) | 0.0275 (4) | |
H9 | 0.825114 | 0.291373 | 0.537238 | 0.033* | |
C10 | 0.6696 (2) | 0.32414 (9) | 0.55451 (3) | 0.0299 (4) | |
C11 | 0.6208 (2) | 0.40515 (9) | 0.52922 (3) | 0.0309 (4) | |
C12 | 0.5567 (2) | 0.45714 (11) | 0.51779 (3) | 0.0457 (6) | |
H12A | 0.513069 | 0.486269 | 0.526982 | 0.069* | |
H12B | 0.488473 | 0.440077 | 0.508720 | 0.069* | |
H12C | 0.626688 | 0.479131 | 0.510181 | 0.069* | |
C13 | 0.6613 (2) | 0.28161 (9) | 0.57142 (3) | 0.0367 (5) | |
C14 | 0.7430 (3) | 0.22917 (11) | 0.57232 (3) | 0.0579 (8) | |
H14 | 0.809072 | 0.221786 | 0.562343 | 0.070* | |
C15 | 0.7281 (4) | 0.18787 (12) | 0.58770 (3) | 0.0705 (10) | |
H15 | 0.785344 | 0.152223 | 0.587982 | 0.085* | |
C16 | 0.5600 (3) | 0.24552 (11) | 0.60151 (3) | 0.0578 (7) | |
H16 | 0.495557 | 0.251916 | 0.611783 | 0.069* | |
C17 | 0.5676 (3) | 0.28933 (11) | 0.58662 (3) | 0.0487 (6) | |
H17 | 0.509201 | 0.324594 | 0.586752 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.1338 (8) | 0.0323 (3) | 0.0154 (3) | 0.000 | 0.000 | 0.000 |
S1 | 0.0360 (3) | 0.0427 (3) | 0.0257 (2) | 0.0163 (2) | 0.0078 (2) | 0.0025 (2) |
O1 | 0.118 (3) | 0.0462 (14) | 0.0306 (11) | 0.000 | 0.000 | 0.0010 (10) |
N1 | 0.125 (2) | 0.0353 (10) | 0.0206 (8) | 0.0184 (12) | 0.0178 (11) | 0.0010 (7) |
C1 | 0.0346 (10) | 0.0259 (9) | 0.0168 (7) | 0.0160 (8) | −0.0004 (7) | 0.0001 (7) |
C2 | 0.0348 (10) | 0.0340 (10) | 0.0180 (8) | 0.0213 (8) | −0.0015 (7) | −0.0016 (7) |
C3 | 0.0417 (12) | 0.0373 (11) | 0.0264 (9) | 0.0163 (9) | −0.0065 (9) | −0.0009 (8) |
C4 | 0.0486 (13) | 0.0483 (13) | 0.0341 (11) | 0.0188 (11) | −0.0146 (10) | −0.0086 (10) |
C5 | 0.0517 (14) | 0.0597 (14) | 0.0221 (9) | 0.0321 (12) | −0.0120 (9) | −0.0069 (9) |
C6 | 0.0504 (13) | 0.0533 (13) | 0.0184 (9) | 0.0318 (11) | 0.0033 (9) | 0.0042 (9) |
C7 | 0.0379 (11) | 0.0420 (11) | 0.0215 (8) | 0.0225 (9) | 0.0037 (8) | 0.0032 (8) |
C8 | 0.0306 (9) | 0.0278 (9) | 0.0172 (7) | 0.0103 (8) | −0.0034 (7) | −0.0016 (7) |
C9 | 0.0361 (10) | 0.0284 (9) | 0.0180 (8) | 0.0133 (8) | −0.0005 (7) | −0.0021 (7) |
C10 | 0.0421 (11) | 0.0288 (9) | 0.0189 (8) | 0.0091 (8) | 0.0012 (8) | −0.0025 (7) |
C11 | 0.0323 (10) | 0.0376 (11) | 0.0226 (8) | 0.0137 (9) | 0.0030 (8) | 0.0041 (8) |
C12 | 0.0511 (14) | 0.0503 (13) | 0.0357 (11) | 0.0323 (11) | 0.0100 (10) | 0.0090 (10) |
C13 | 0.0602 (14) | 0.0317 (10) | 0.0181 (8) | 0.0070 (10) | 0.0043 (9) | −0.0017 (7) |
C14 | 0.098 (2) | 0.0496 (14) | 0.0264 (10) | 0.0351 (14) | 0.0215 (12) | 0.0105 (10) |
C15 | 0.135 (3) | 0.0476 (14) | 0.0292 (11) | 0.0425 (17) | 0.0250 (15) | 0.0113 (10) |
C16 | 0.104 (2) | 0.0427 (13) | 0.0265 (10) | 0.0126 (14) | 0.0246 (12) | 0.0003 (9) |
C17 | 0.0813 (18) | 0.0383 (12) | 0.0267 (10) | 0.0166 (12) | 0.0172 (11) | 0.0029 (9) |
Co1—O1 | 2.096 (3) | C5—C6 | 1.375 (3) |
Co1—O1i | 2.096 (3) | C6—H6 | 0.9500 |
Co1—N1i | 2.1458 (18) | C6—C7 | 1.394 (3) |
Co1—N1ii | 2.1458 (18) | C7—H7 | 0.9500 |
Co1—N1 | 2.1459 (18) | C8—C9 | 1.423 (2) |
Co1—N1iii | 2.1458 (18) | C8—C11 | 1.370 (3) |
S1—C10 | 1.7218 (19) | C9—H9 | 0.9500 |
S1—C11 | 1.7163 (19) | C9—C10 | 1.368 (2) |
O1—H1A | 1.0111 | C10—C13 | 1.464 (3) |
O1—H1B | 1.0112 | C11—C12 | 1.495 (3) |
N1—C15 | 1.339 (3) | C12—H12A | 0.9800 |
N1—C16 | 1.328 (3) | C12—H12B | 0.9800 |
C1—C1iv | 1.353 (4) | C12—H12C | 0.9800 |
C1—C2 | 1.495 (2) | C13—C14 | 1.384 (3) |
C1—C8 | 1.487 (2) | C13—C17 | 1.389 (3) |
C2—C3 | 1.389 (3) | C14—H14 | 0.9500 |
C2—C7 | 1.397 (3) | C14—C15 | 1.373 (3) |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C3—C4 | 1.394 (3) | C16—H16 | 0.9500 |
C4—H4 | 0.9500 | C16—C17 | 1.378 (3) |
C4—C5 | 1.382 (3) | C17—H17 | 0.9500 |
C5—H5 | 0.9500 | ||
O1—Co1—O1i | 180.0 | C5—C6—C7 | 120.7 (2) |
O1—Co1—N1ii | 93.27 (8) | C7—C6—H6 | 119.7 |
O1i—Co1—N1iii | 93.27 (8) | C2—C7—H7 | 119.9 |
O1i—Co1—N1 | 93.27 (7) | C6—C7—C2 | 120.3 (2) |
O1—Co1—N1i | 93.27 (7) | C6—C7—H7 | 119.9 |
O1i—Co1—N1ii | 86.73 (7) | C9—C8—C1 | 123.85 (15) |
O1i—Co1—N1i | 86.73 (8) | C11—C8—C1 | 124.29 (16) |
O1—Co1—N1 | 86.73 (8) | C11—C8—C9 | 111.85 (16) |
O1—Co1—N1iii | 86.73 (7) | C8—C9—H9 | 123.2 |
N1iii—Co1—N1 | 173.45 (15) | C10—C9—C8 | 113.70 (16) |
N1ii—Co1—N1iii | 88.99 (10) | C10—C9—H9 | 123.2 |
N1ii—Co1—N1 | 91.39 (10) | C9—C10—S1 | 110.39 (14) |
N1i—Co1—N1ii | 173.45 (15) | C9—C10—C13 | 128.60 (18) |
N1i—Co1—N1 | 88.98 (10) | C13—C10—S1 | 120.91 (15) |
N1i—Co1—N1iii | 91.39 (10) | C8—C11—S1 | 111.53 (13) |
C11—S1—C10 | 92.49 (9) | C8—C11—C12 | 128.79 (17) |
Co1—O1—H1A | 128.9 | C12—C11—S1 | 119.67 (14) |
Co1—O1—H1B | 128.9 | C11—C12—H12A | 109.5 |
H1A—O1—H1B | 102.2 | C11—C12—H12B | 109.5 |
C15—N1—Co1 | 119.07 (16) | C11—C12—H12C | 109.5 |
C16—N1—Co1 | 124.63 (16) | H12A—C12—H12B | 109.5 |
C16—N1—C15 | 116.3 (2) | H12A—C12—H12C | 109.5 |
C1iv—C1—C2 | 122.90 (10) | H12B—C12—H12C | 109.5 |
C1iv—C1—C8 | 121.21 (10) | C14—C13—C10 | 120.53 (18) |
C8—C1—C2 | 115.88 (16) | C14—C13—C17 | 116.74 (19) |
C3—C2—C1 | 120.37 (17) | C17—C13—C10 | 122.64 (19) |
C3—C2—C7 | 118.45 (17) | C13—C14—H14 | 120.2 |
C7—C2—C1 | 121.14 (19) | C15—C14—C13 | 119.7 (2) |
C2—C3—H3 | 119.6 | C15—C14—H14 | 120.2 |
C2—C3—C4 | 120.8 (2) | N1—C15—C14 | 123.8 (2) |
C4—C3—H3 | 119.6 | N1—C15—H15 | 118.1 |
C3—C4—H4 | 119.9 | C14—C15—H15 | 118.1 |
C5—C4—C3 | 120.2 (2) | N1—C16—H16 | 118.1 |
C5—C4—H4 | 119.9 | N1—C16—C17 | 123.8 (2) |
C4—C5—H5 | 120.2 | C17—C16—H16 | 118.1 |
C6—C5—C4 | 119.61 (19) | C13—C17—H17 | 120.2 |
C6—C5—H5 | 120.2 | C16—C17—C13 | 119.6 (2) |
C5—C6—H6 | 119.7 | C16—C17—H17 | 120.2 |
Co1—N1—C15—C14 | 178.9 (3) | C7—C2—C3—C4 | 1.5 (3) |
Co1—N1—C16—C17 | −178.7 (2) | C8—C1—C2—C3 | −44.7 (2) |
S1—C10—C13—C14 | 173.2 (2) | C8—C1—C2—C7 | 132.92 (18) |
S1—C10—C13—C17 | −3.1 (3) | C8—C9—C10—S1 | −0.7 (2) |
N1—C16—C17—C13 | −0.4 (4) | C8—C9—C10—C13 | 175.4 (2) |
C1iv—C1—C2—C3 | 134.1 (2) | C9—C8—C11—S1 | 1.8 (2) |
C1iv—C1—C2—C7 | −48.3 (3) | C9—C8—C11—C12 | −177.0 (2) |
C1iv—C1—C8—C9 | −49.7 (3) | C9—C10—C13—C14 | −2.6 (4) |
C1iv—C1—C8—C11 | 131.5 (2) | C9—C10—C13—C17 | −178.9 (2) |
C1—C2—C3—C4 | 179.15 (17) | C10—S1—C11—C8 | −1.90 (17) |
C1—C2—C7—C6 | −178.47 (16) | C10—S1—C11—C12 | 177.06 (19) |
C1—C8—C9—C10 | −179.59 (18) | C10—C13—C14—C15 | −176.1 (3) |
C1—C8—C11—S1 | −179.31 (15) | C10—C13—C17—C16 | 176.2 (2) |
C1—C8—C11—C12 | 1.9 (4) | C11—S1—C10—C9 | 1.48 (17) |
C2—C1—C8—C9 | 129.11 (19) | C11—S1—C10—C13 | −175.00 (18) |
C2—C1—C8—C11 | −49.7 (3) | C11—C8—C9—C10 | −0.7 (3) |
C2—C3—C4—C5 | −1.3 (3) | C13—C14—C15—N1 | 0.0 (5) |
C3—C2—C7—C6 | −0.8 (3) | C14—C13—C17—C16 | −0.2 (4) |
C3—C4—C5—C6 | 0.4 (3) | C15—N1—C16—C17 | 0.7 (5) |
C4—C5—C6—C7 | 0.2 (3) | C16—N1—C15—C14 | −0.5 (5) |
C5—C6—C7—C2 | 0.0 (3) | C17—C13—C14—C15 | 0.4 (4) |
Symmetry codes: (i) −x+5/4, −y+1/4, z; (ii) −x+5/4, y, −z+5/4; (iii) x, −y+1/4, −z+5/4; (iv) −x+7/4, −y+3/4, z. |
C68H56N4NiO2S4 | Dx = 1.067 Mg m−3 |
Mr = 1148.11 | Synchrotron radiation, λ = 0.41328 Å |
Orthorhombic, Fddd | Cell parameters from 9920 reflections |
a = 9.8621 (6) Å | θ = 2.4–16.5° |
b = 21.6164 (13) Å | µ = 0.11 mm−1 |
c = 67.069 (4) Å | T = 100 K |
V = 14298.1 (15) Å3 | Prism, green |
Z = 8 | 0.04 × 0.02 × 0.02 mm |
F(000) = 4800 |
PILATUS3 1M diffractometer | 2604 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.060 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0730 before and 0.0572 after correction. The Ratio of minimum to maximum transmission is 0.9125. The λ/2 correction factor is Not present. | θmax = 14.1°, θmin = 1.3° |
Tmin = 0.679, Tmax = 0.744 | h = −11→11 |
71940 measured reflections | k = −24→24 |
3003 independent reflections | l = −78→78 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0406P)2 + 34.8474P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.003 |
3003 reflections | Δρmax = 0.24 e Å−3 |
182 parameters | Δρmin = −0.35 e Å−3 |
0 restraints |
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) | |
Ni1 | 0.625000 | 0.625000 | 0.625000 | 0.04067 (18) | |
S1 | 0.69450 (6) | 0.36619 (3) | 0.55243 (2) | 0.04071 (17) | |
O1 | 0.8373 (3) | 0.625000 | 0.625000 | 0.0516 (6) | |
H1A | 0.894404 | 0.598282 | 0.618539 | 0.077* | 0.5 |
H1B | 0.894404 | 0.651728 | 0.631461 | 0.077* | 0.5 |
N1 | 0.6147 (2) | 0.55723 (8) | 0.60271 (2) | 0.0427 (5) | |
C1 | 0.4434 (2) | 0.37571 (8) | 0.50540 (3) | 0.0304 (4) | |
C2 | 0.5265 (2) | 0.37187 (9) | 0.48673 (3) | 0.0313 (4) | |
C3 | 0.6345 (2) | 0.41236 (10) | 0.48373 (3) | 0.0374 (5) | |
H3 | 0.654322 | 0.442890 | 0.493497 | 0.045* | |
C4 | 0.7138 (2) | 0.40856 (11) | 0.46660 (3) | 0.0429 (5) | |
H4 | 0.786664 | 0.436669 | 0.464695 | 0.051* | |
C5 | 0.6866 (2) | 0.36392 (11) | 0.45232 (3) | 0.0448 (6) | |
H5 | 0.740550 | 0.361419 | 0.440614 | 0.054* | |
C6 | 0.5810 (2) | 0.32320 (11) | 0.45521 (3) | 0.0425 (6) | |
H6 | 0.562657 | 0.292385 | 0.445483 | 0.051* | |
C7 | 0.5012 (2) | 0.32680 (10) | 0.47225 (3) | 0.0361 (5) | |
H7 | 0.428759 | 0.298379 | 0.474065 | 0.043* | |
C8 | 0.5217 (2) | 0.38195 (9) | 0.52441 (3) | 0.0297 (4) | |
C9 | 0.4959 (2) | 0.42861 (9) | 0.53887 (3) | 0.0304 (4) | |
H9 | 0.425832 | 0.458481 | 0.537506 | 0.036* | |
C10 | 0.5814 (2) | 0.42645 (9) | 0.55492 (3) | 0.0333 (5) | |
C11 | 0.6289 (2) | 0.34549 (10) | 0.52962 (3) | 0.0359 (5) | |
C12 | 0.6935 (3) | 0.29337 (11) | 0.51819 (3) | 0.0466 (6) | |
H12A | 0.739974 | 0.265557 | 0.527485 | 0.070* | |
H12B | 0.759262 | 0.310249 | 0.508675 | 0.070* | |
H12C | 0.623433 | 0.270366 | 0.510954 | 0.070* | |
C13 | 0.5909 (2) | 0.46964 (9) | 0.57174 (3) | 0.0357 (5) | |
C14 | 0.5086 (3) | 0.52164 (11) | 0.57268 (3) | 0.0470 (6) | |
H14 | 0.441750 | 0.528277 | 0.562710 | 0.056* | |
C15 | 0.5231 (3) | 0.56346 (11) | 0.58788 (3) | 0.0517 (7) | |
H15 | 0.465677 | 0.598740 | 0.587995 | 0.062* | |
C16 | 0.6937 (3) | 0.50695 (11) | 0.60192 (3) | 0.0456 (6) | |
H16 | 0.759081 | 0.501350 | 0.612154 | 0.055* | |
C17 | 0.6857 (3) | 0.46272 (10) | 0.58710 (3) | 0.0434 (5) | |
H17 | 0.744254 | 0.427821 | 0.587333 | 0.052* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0749 (4) | 0.0320 (3) | 0.0152 (3) | 0.000 | 0.000 | 0.000 |
S1 | 0.0508 (4) | 0.0410 (3) | 0.0303 (3) | 0.0145 (2) | −0.0087 (2) | −0.0056 (2) |
O1 | 0.0743 (17) | 0.0511 (14) | 0.0296 (11) | 0.000 | 0.000 | −0.0008 (10) |
N1 | 0.0746 (14) | 0.0342 (10) | 0.0193 (8) | 0.0059 (9) | −0.0073 (8) | 0.0001 (7) |
C1 | 0.0473 (11) | 0.0226 (10) | 0.0212 (9) | 0.0067 (9) | 0.0000 (8) | 0.0005 (7) |
C2 | 0.0433 (12) | 0.0285 (10) | 0.0220 (9) | 0.0111 (8) | −0.0001 (8) | 0.0010 (7) |
C3 | 0.0476 (13) | 0.0349 (11) | 0.0295 (10) | 0.0062 (9) | 0.0029 (9) | −0.0004 (8) |
C4 | 0.0466 (13) | 0.0466 (14) | 0.0354 (11) | 0.0069 (10) | 0.0072 (10) | 0.0068 (9) |
C5 | 0.0518 (14) | 0.0574 (15) | 0.0250 (10) | 0.0202 (12) | 0.0038 (10) | 0.0032 (9) |
C6 | 0.0541 (14) | 0.0497 (14) | 0.0236 (10) | 0.0204 (11) | −0.0054 (9) | −0.0074 (9) |
C7 | 0.0470 (13) | 0.0360 (11) | 0.0252 (10) | 0.0104 (9) | −0.0032 (9) | −0.0024 (8) |
C8 | 0.0411 (11) | 0.0276 (10) | 0.0202 (9) | 0.0028 (8) | 0.0018 (8) | 0.0009 (7) |
C9 | 0.0440 (12) | 0.0255 (10) | 0.0216 (9) | 0.0052 (8) | −0.0003 (8) | 0.0010 (7) |
C10 | 0.0472 (12) | 0.0308 (11) | 0.0219 (9) | 0.0045 (9) | 0.0006 (8) | 0.0013 (7) |
C11 | 0.0445 (12) | 0.0352 (11) | 0.0279 (10) | 0.0071 (9) | −0.0028 (9) | −0.0044 (8) |
C12 | 0.0597 (15) | 0.0399 (13) | 0.0401 (12) | 0.0202 (11) | −0.0073 (11) | −0.0085 (10) |
C13 | 0.0543 (14) | 0.0320 (11) | 0.0207 (9) | 0.0025 (9) | −0.0026 (9) | 0.0005 (8) |
C14 | 0.0694 (16) | 0.0457 (13) | 0.0258 (10) | 0.0174 (11) | −0.0139 (10) | −0.0068 (9) |
C15 | 0.0872 (19) | 0.0425 (13) | 0.0254 (11) | 0.0236 (13) | −0.0109 (11) | −0.0055 (9) |
C16 | 0.0695 (16) | 0.0429 (13) | 0.0243 (10) | 0.0098 (12) | −0.0117 (10) | −0.0013 (9) |
C17 | 0.0666 (15) | 0.0369 (12) | 0.0266 (11) | 0.0121 (11) | −0.0085 (10) | −0.0019 (8) |
Ni1—O1i | 2.093 (3) | C5—C6 | 1.377 (4) |
Ni1—O1 | 2.093 (3) | C6—H6 | 0.9500 |
Ni1—N1 | 2.0955 (17) | C6—C7 | 1.390 (3) |
Ni1—N1ii | 2.0957 (17) | C7—H7 | 0.9500 |
Ni1—N1iii | 2.0957 (17) | C8—C9 | 1.422 (3) |
Ni1—N1i | 2.0957 (17) | C8—C11 | 1.364 (3) |
S1—C10 | 1.723 (2) | C9—H9 | 0.9500 |
S1—C11 | 1.721 (2) | C9—C10 | 1.369 (3) |
O1—H1A | 0.9159 | C10—C13 | 1.467 (3) |
O1—H1B | 0.9160 | C11—C12 | 1.504 (3) |
N1—C15 | 1.350 (3) | C12—H12A | 0.9800 |
N1—C16 | 1.338 (3) | C12—H12B | 0.9800 |
C1—C1iv | 1.349 (4) | C12—H12C | 0.9800 |
C1—C2 | 1.499 (3) | C13—C14 | 1.388 (3) |
C1—C8 | 1.497 (3) | C13—C17 | 1.399 (3) |
C2—C3 | 1.393 (3) | C14—H14 | 0.9500 |
C2—C7 | 1.398 (3) | C14—C15 | 1.370 (3) |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C3—C4 | 1.392 (3) | C16—H16 | 0.9500 |
C4—H4 | 0.9500 | C16—C17 | 1.382 (3) |
C4—C5 | 1.386 (3) | C17—H17 | 0.9500 |
C5—H5 | 0.9500 | ||
O1i—Ni1—O1 | 180.0 | C5—C6—C7 | 120.6 (2) |
O1i—Ni1—N1ii | 87.21 (6) | C7—C6—H6 | 119.7 |
O1—Ni1—N1i | 87.21 (6) | C2—C7—H7 | 119.7 |
O1—Ni1—N1iii | 87.21 (6) | C6—C7—C2 | 120.6 (2) |
O1i—Ni1—N1 | 87.21 (6) | C6—C7—H7 | 119.7 |
O1—Ni1—N1ii | 92.79 (6) | C9—C8—C1 | 123.51 (17) |
O1—Ni1—N1 | 92.79 (6) | C11—C8—C1 | 124.48 (17) |
O1i—Ni1—N1iii | 92.79 (6) | C11—C8—C9 | 111.97 (17) |
O1i—Ni1—N1i | 92.79 (6) | C8—C9—H9 | 123.2 |
N1i—Ni1—N1iii | 174.42 (12) | C10—C9—C8 | 113.69 (18) |
N1ii—Ni1—N1i | 91.29 (9) | C10—C9—H9 | 123.2 |
N1ii—Ni1—N1iii | 88.98 (9) | C9—C10—S1 | 110.40 (14) |
N1—Ni1—N1ii | 174.42 (12) | C9—C10—C13 | 128.50 (19) |
N1—Ni1—N1iii | 91.29 (9) | C13—C10—S1 | 120.95 (16) |
N1—Ni1—N1i | 88.98 (9) | C8—C11—S1 | 111.66 (15) |
C11—S1—C10 | 92.25 (10) | C8—C11—C12 | 129.10 (19) |
Ni1—O1—H1A | 128.0 | C12—C11—S1 | 119.24 (16) |
Ni1—O1—H1B | 128.0 | C11—C12—H12A | 109.5 |
H1A—O1—H1B | 104.1 | C11—C12—H12B | 109.5 |
C15—N1—Ni1 | 119.22 (15) | C11—C12—H12C | 109.5 |
C16—N1—Ni1 | 124.60 (14) | H12A—C12—H12B | 109.5 |
C16—N1—C15 | 116.17 (18) | H12A—C12—H12C | 109.5 |
C1iv—C1—C2 | 123.04 (11) | H12B—C12—H12C | 109.5 |
C1iv—C1—C8 | 121.21 (11) | C14—C13—C10 | 120.86 (18) |
C8—C1—C2 | 115.75 (17) | C14—C13—C17 | 116.36 (19) |
C3—C2—C1 | 120.23 (17) | C17—C13—C10 | 122.72 (19) |
C3—C2—C7 | 118.30 (18) | C13—C14—H14 | 119.8 |
C7—C2—C1 | 121.44 (19) | C15—C14—C13 | 120.5 (2) |
C2—C3—H3 | 119.6 | C15—C14—H14 | 119.8 |
C4—C3—C2 | 120.7 (2) | N1—C15—C14 | 123.5 (2) |
C4—C3—H3 | 119.6 | N1—C15—H15 | 118.2 |
C3—C4—H4 | 119.9 | C14—C15—H15 | 118.2 |
C5—C4—C3 | 120.2 (2) | N1—C16—H16 | 118.0 |
C5—C4—H4 | 119.9 | N1—C16—C17 | 123.9 (2) |
C4—C5—H5 | 120.2 | C17—C16—H16 | 118.0 |
C6—C5—C4 | 119.6 (2) | C13—C17—H17 | 120.2 |
C6—C5—H5 | 120.2 | C16—C17—C13 | 119.6 (2) |
C5—C6—H6 | 119.7 | C16—C17—H17 | 120.2 |
Ni1—N1—C15—C14 | −179.9 (2) | C7—C2—C3—C4 | 1.0 (3) |
Ni1—N1—C16—C17 | −179.90 (19) | C8—C1—C2—C3 | −45.3 (2) |
S1—C10—C13—C14 | 173.51 (18) | C8—C1—C2—C7 | 132.57 (19) |
S1—C10—C13—C17 | −3.6 (3) | C8—C9—C10—S1 | −0.4 (2) |
N1—C16—C17—C13 | 0.3 (4) | C8—C9—C10—C13 | 175.0 (2) |
C1iv—C1—C2—C3 | 134.1 (3) | C9—C8—C11—S1 | 2.0 (2) |
C1iv—C1—C2—C7 | −48.0 (3) | C9—C8—C11—C12 | −176.7 (2) |
C1iv—C1—C8—C9 | −51.0 (3) | C9—C10—C13—C14 | −1.4 (4) |
C1iv—C1—C8—C11 | 131.6 (3) | C9—C10—C13—C17 | −178.6 (2) |
C1—C2—C3—C4 | 178.94 (18) | C10—S1—C11—C8 | −1.95 (18) |
C1—C2—C7—C6 | −178.71 (18) | C10—S1—C11—C12 | 176.94 (19) |
C1—C8—C9—C10 | −178.77 (18) | C10—C13—C14—C15 | −176.5 (2) |
C1—C8—C11—S1 | 179.73 (16) | C10—C13—C17—C16 | 176.6 (2) |
C1—C8—C11—C12 | 1.0 (4) | C11—S1—C10—C9 | 1.33 (17) |
C2—C1—C8—C9 | 128.5 (2) | C11—S1—C10—C13 | −174.45 (18) |
C2—C1—C8—C11 | −49.0 (3) | C11—C8—C9—C10 | −1.1 (3) |
C2—C3—C4—C5 | −0.5 (3) | C13—C14—C15—N1 | −0.6 (4) |
C3—C2—C7—C6 | −0.8 (3) | C14—C13—C17—C16 | −0.6 (3) |
C3—C4—C5—C6 | −0.2 (3) | C15—N1—C16—C17 | 0.0 (4) |
C4—C5—C6—C7 | 0.4 (3) | C16—N1—C15—C14 | 0.2 (4) |
C5—C6—C7—C2 | 0.1 (3) | C17—C13—C14—C15 | 0.8 (4) |
Symmetry codes: (i) −x+5/4, −y+5/4, z; (ii) x, −y+5/4, −z+5/4; (iii) −x+5/4, y, −z+5/4; (iv) −x+3/4, −y+3/4, z. |
C68H56N4O2S4Zn·2(NO3) | Dx = 1.193 Mg m−3 |
Mr = 1278.79 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Fddd | Cell parameters from 9836 reflections |
a = 9.8296 (5) Å | θ = 2.3–29.9° |
b = 21.4844 (12) Å | µ = 0.52 mm−1 |
c = 67.400 (4) Å | T = 90 K |
V = 14233.7 (13) Å3 | Prism, colourless |
Z = 8 | 0.16 × 0.16 × 0.02 mm |
F(000) = 5312 |
Bruker APEX-II CCD diffractometer | 4767 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.048 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1353 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.8796. The λ/2 correction factor is Not present. | θmax = 30.6°, θmin = 2.0° |
Tmin = 0.656, Tmax = 0.746 | h = −13→14 |
47600 measured reflections | k = −30→30 |
5466 independent reflections | l = −96→75 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.086 | H-atom parameters constrained |
wR(F2) = 0.227 | w = 1/[σ2(Fo2) + (0.0791P)2 + 179.9462P] where P = (Fo2 + 2Fc2)/3 |
S = 1.21 | (Δ/σ)max = 0.001 |
5466 reflections | Δρmax = 1.09 e Å−3 |
243 parameters | Δρmin = −0.50 e Å−3 |
86 restraints |
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) | |
Zn1 | 0.625000 | 0.625000 | 0.625000 | 0.0291 (2) | |
S1 | 0.69323 (9) | 0.36467 (4) | 0.55203 (2) | 0.0246 (2) | |
O1 | 0.8446 (5) | 0.625000 | 0.625000 | 0.0403 (10) | |
H1A | 0.888873 | 0.651473 | 0.614628 | 0.060* | 0.5 |
H1B | 0.888873 | 0.584528 | 0.621473 | 0.060* | 0.5 |
N1 | 0.6128 (4) | 0.55515 (14) | 0.60233 (4) | 0.0318 (7) | |
C1 | 0.4440 (3) | 0.37558 (14) | 0.50519 (4) | 0.0165 (5) | |
C2 | 0.5269 (3) | 0.37173 (14) | 0.48664 (4) | 0.0183 (6) | |
C3 | 0.6350 (3) | 0.41246 (16) | 0.48369 (5) | 0.0238 (6) | |
H3 | 0.655270 | 0.443094 | 0.493416 | 0.029* | |
C4 | 0.7136 (4) | 0.40860 (18) | 0.46660 (5) | 0.0285 (7) | |
H4 | 0.786604 | 0.436894 | 0.464639 | 0.034* | |
C5 | 0.6857 (4) | 0.36339 (19) | 0.45232 (5) | 0.0307 (8) | |
H5 | 0.739719 | 0.360681 | 0.440655 | 0.037* | |
C6 | 0.5801 (4) | 0.32299 (18) | 0.45524 (5) | 0.0288 (8) | |
H6 | 0.561027 | 0.292199 | 0.445514 | 0.035* | |
C7 | 0.5001 (3) | 0.32634 (16) | 0.47227 (5) | 0.0223 (6) | |
H7 | 0.427427 | 0.297792 | 0.474123 | 0.027* | |
C8 | 0.5216 (3) | 0.38186 (14) | 0.52409 (4) | 0.0170 (5) | |
C9 | 0.4945 (3) | 0.42826 (14) | 0.53851 (4) | 0.0164 (5) | |
H9 | 0.424084 | 0.458274 | 0.537181 | 0.020* | |
C10 | 0.5802 (3) | 0.42551 (14) | 0.55463 (4) | 0.0182 (5) | |
C11 | 0.6288 (3) | 0.34465 (15) | 0.52929 (4) | 0.0218 (6) | |
C12 | 0.6932 (4) | 0.29264 (18) | 0.51781 (5) | 0.0318 (8) | |
H12A | 0.761667 | 0.309694 | 0.508740 | 0.048* | |
H12B | 0.623268 | 0.270717 | 0.510155 | 0.048* | |
H12C | 0.736809 | 0.263525 | 0.527017 | 0.048* | |
C13 | 0.5894 (3) | 0.46829 (15) | 0.57147 (4) | 0.0202 (6) | |
C14 | 0.5054 (4) | 0.52045 (18) | 0.57239 (5) | 0.0313 (8) | |
H14 | 0.438540 | 0.527312 | 0.562451 | 0.038* | |
C15 | 0.5201 (5) | 0.56204 (18) | 0.58781 (5) | 0.0370 (10) | |
H15 | 0.461953 | 0.597323 | 0.588205 | 0.044* | |
C16 | 0.6924 (4) | 0.50497 (17) | 0.60165 (5) | 0.0305 (8) | |
H16 | 0.758085 | 0.499420 | 0.611842 | 0.037* | |
C17 | 0.6841 (4) | 0.46034 (16) | 0.58673 (5) | 0.0280 (7) | |
H17 | 0.742018 | 0.424939 | 0.586919 | 0.034* | |
N2 | 1.0701 (7) | 0.5278 (4) | 0.59290 (12) | 0.060 (3) | 0.335 (6) |
O2 | 1.0161 (9) | 0.5791 (4) | 0.59596 (15) | 0.040 (3) | 0.335 (6) |
O3 | 1.0170 (13) | 0.4793 (5) | 0.5998 (2) | 0.093 (5) | 0.335 (6) |
O4 | 1.1779 (11) | 0.5245 (5) | 0.5831 (2) | 0.089 (5) | 0.335 (6) |
N2A | 1.1391 (17) | 0.5768 (9) | 0.6006 (2) | 0.131 (14) | 0.165 (6) |
O2A | 1.0148 (17) | 0.5638 (15) | 0.6010 (4) | 0.084 (9) | 0.165 (6) |
O3A | 1.224 (2) | 0.5413 (9) | 0.6085 (3) | 0.060 (6) | 0.165 (6) |
O4A | 1.178 (2) | 0.6252 (10) | 0.5922 (3) | 0.086 (8) | 0.165 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0573 (6) | 0.0211 (4) | 0.0090 (3) | 0.000 | 0.000 | 0.000 |
S1 | 0.0237 (4) | 0.0293 (4) | 0.0208 (4) | 0.0144 (3) | −0.0074 (3) | −0.0050 (3) |
O1 | 0.056 (3) | 0.039 (2) | 0.0257 (18) | 0.000 | 0.000 | 0.0051 (17) |
N1 | 0.059 (2) | 0.0218 (13) | 0.0144 (11) | 0.0088 (14) | −0.0098 (13) | −0.0023 (10) |
C1 | 0.0210 (14) | 0.0167 (12) | 0.0119 (11) | 0.0090 (10) | −0.0001 (10) | −0.0014 (10) |
C2 | 0.0201 (13) | 0.0216 (13) | 0.0133 (11) | 0.0118 (11) | 0.0009 (10) | 0.0009 (10) |
C3 | 0.0242 (15) | 0.0253 (15) | 0.0217 (14) | 0.0096 (12) | 0.0038 (12) | 0.0003 (12) |
C4 | 0.0224 (16) | 0.0354 (18) | 0.0277 (16) | 0.0077 (13) | 0.0091 (13) | 0.0069 (14) |
C5 | 0.0289 (17) | 0.044 (2) | 0.0187 (14) | 0.0211 (16) | 0.0064 (13) | 0.0051 (14) |
C6 | 0.0317 (18) | 0.0395 (19) | 0.0153 (13) | 0.0198 (15) | −0.0033 (12) | −0.0055 (13) |
C7 | 0.0222 (15) | 0.0269 (15) | 0.0179 (13) | 0.0129 (12) | −0.0026 (11) | −0.0045 (11) |
C8 | 0.0195 (13) | 0.0172 (12) | 0.0144 (12) | 0.0070 (10) | 0.0008 (10) | −0.0010 (10) |
C9 | 0.0177 (13) | 0.0184 (12) | 0.0130 (11) | 0.0073 (10) | −0.0014 (10) | −0.0010 (9) |
C10 | 0.0220 (14) | 0.0193 (13) | 0.0132 (12) | 0.0060 (11) | −0.0011 (10) | 0.0002 (10) |
C11 | 0.0222 (14) | 0.0262 (15) | 0.0171 (13) | 0.0110 (12) | −0.0046 (11) | −0.0043 (11) |
C12 | 0.0359 (19) | 0.0334 (18) | 0.0260 (16) | 0.0242 (16) | −0.0084 (14) | −0.0108 (14) |
C13 | 0.0277 (16) | 0.0223 (14) | 0.0107 (11) | 0.0045 (12) | −0.0025 (11) | −0.0002 (10) |
C14 | 0.043 (2) | 0.0335 (18) | 0.0174 (14) | 0.0183 (16) | −0.0130 (14) | −0.0069 (13) |
C15 | 0.061 (3) | 0.0301 (17) | 0.0203 (16) | 0.0198 (18) | −0.0122 (16) | −0.0073 (13) |
C16 | 0.045 (2) | 0.0290 (16) | 0.0169 (14) | 0.0083 (15) | −0.0113 (14) | −0.0027 (12) |
C17 | 0.0388 (19) | 0.0260 (15) | 0.0193 (14) | 0.0086 (14) | −0.0112 (14) | −0.0041 (12) |
N2 | 0.046 (6) | 0.083 (7) | 0.051 (7) | 0.019 (5) | 0.007 (5) | 0.007 (5) |
O2 | 0.034 (5) | 0.070 (6) | 0.017 (5) | 0.024 (4) | 0.000 (3) | 0.014 (4) |
O3 | 0.070 (8) | 0.109 (8) | 0.100 (11) | 0.004 (6) | 0.010 (8) | 0.022 (7) |
O4 | 0.066 (7) | 0.072 (8) | 0.128 (12) | 0.010 (6) | 0.045 (8) | −0.008 (8) |
N2A | 0.077 (12) | 0.169 (19) | 0.15 (3) | 0.017 (12) | 0.004 (10) | 0.057 (19) |
O2A | 0.071 (11) | 0.15 (2) | 0.031 (15) | 0.019 (12) | 0.013 (9) | −0.017 (14) |
O3A | 0.053 (11) | 0.077 (14) | 0.052 (12) | −0.013 (9) | −0.005 (9) | −0.025 (9) |
O4A | 0.087 (15) | 0.128 (16) | 0.042 (11) | 0.033 (13) | 0.033 (10) | −0.005 (11) |
Zn1—O1i | 2.158 (5) | C7—H7 | 0.9500 |
Zn1—O1 | 2.158 (5) | C8—C9 | 1.418 (4) |
Zn1—N1 | 2.145 (3) | C8—C11 | 1.368 (4) |
Zn1—N1ii | 2.145 (3) | C9—H9 | 0.9500 |
Zn1—N1i | 2.145 (3) | C9—C10 | 1.376 (4) |
Zn1—N1iii | 2.145 (3) | C10—C13 | 1.463 (4) |
S1—C10 | 1.724 (3) | C11—C12 | 1.500 (4) |
S1—C11 | 1.714 (3) | C12—H12A | 0.9800 |
O1—H1A | 1.0010 | C12—H12B | 0.9800 |
O1—H1B | 1.0012 | C12—H12C | 0.9800 |
N1—C15 | 1.345 (5) | C13—C14 | 1.393 (5) |
N1—C16 | 1.333 (5) | C13—C17 | 1.398 (4) |
C1—C1iv | 1.356 (6) | C14—H14 | 0.9500 |
C1—C2 | 1.494 (4) | C14—C15 | 1.379 (5) |
C1—C8 | 1.491 (4) | C15—H15 | 0.9500 |
C2—C3 | 1.391 (5) | C16—H16 | 0.9500 |
C2—C7 | 1.400 (4) | C16—C17 | 1.392 (5) |
C3—H3 | 0.9500 | C17—H17 | 0.9500 |
C3—C4 | 1.389 (5) | N2—O2 | 1.2407 |
C4—H4 | 0.9500 | N2—O3 | 1.2538 |
C4—C5 | 1.395 (6) | N2—O4 | 1.2511 |
C5—H5 | 0.9500 | N2A—O2A | 1.2530 |
C5—C6 | 1.367 (6) | N2A—O3A | 1.2509 |
C6—H6 | 0.9500 | N2A—O4A | 1.2418 |
C6—C7 | 1.393 (5) | ||
O1—Zn1—O1i | 180.0 | C6—C7—C2 | 120.0 (3) |
N1iii—Zn1—O1 | 93.21 (11) | C6—C7—H7 | 120.0 |
N1ii—Zn1—O1i | 93.21 (11) | C9—C8—C1 | 123.6 (2) |
N1—Zn1—O1i | 86.78 (11) | C11—C8—C1 | 124.1 (3) |
N1iii—Zn1—O1i | 86.79 (11) | C11—C8—C9 | 112.3 (3) |
N1ii—Zn1—O1 | 86.79 (11) | C8—C9—H9 | 123.3 |
N1—Zn1—O1 | 93.22 (11) | C10—C9—C8 | 113.3 (3) |
N1i—Zn1—O1i | 93.21 (11) | C10—C9—H9 | 123.3 |
N1i—Zn1—O1 | 86.79 (11) | C9—C10—S1 | 110.3 (2) |
N1iii—Zn1—N1 | 173.6 (2) | C9—C10—C13 | 128.5 (3) |
N1ii—Zn1—N1i | 173.6 (2) | C13—C10—S1 | 121.0 (2) |
N1iii—Zn1—N1ii | 89.14 (16) | C8—C11—S1 | 111.6 (2) |
N1ii—Zn1—N1 | 91.22 (16) | C8—C11—C12 | 128.9 (3) |
N1i—Zn1—N1 | 89.14 (16) | C12—C11—S1 | 119.5 (2) |
N1iii—Zn1—N1i | 91.22 (16) | C11—C12—H12A | 109.5 |
C11—S1—C10 | 92.46 (15) | C11—C12—H12B | 109.5 |
Zn1—O1—H1A | 115.8 | C11—C12—H12C | 109.5 |
Zn1—O1—H1B | 115.8 | H12A—C12—H12B | 109.5 |
H1A—O1—H1B | 97.9 | H12A—C12—H12C | 109.5 |
C15—N1—Zn1 | 118.6 (2) | H12B—C12—H12C | 109.5 |
C16—N1—Zn1 | 123.8 (2) | C14—C13—C10 | 120.2 (3) |
C16—N1—C15 | 117.5 (3) | C14—C13—C17 | 117.4 (3) |
C1iv—C1—C2 | 122.96 (17) | C17—C13—C10 | 122.3 (3) |
C1iv—C1—C8 | 120.90 (16) | C13—C14—H14 | 120.2 |
C8—C1—C2 | 116.1 (3) | C15—C14—C13 | 119.5 (3) |
C3—C2—C1 | 120.1 (3) | C15—C14—H14 | 120.2 |
C3—C2—C7 | 118.9 (3) | N1—C15—C14 | 123.3 (3) |
C7—C2—C1 | 121.0 (3) | N1—C15—H15 | 118.4 |
C2—C3—H3 | 119.8 | C14—C15—H15 | 118.4 |
C4—C3—C2 | 120.4 (3) | N1—C16—H16 | 118.4 |
C4—C3—H3 | 119.8 | N1—C16—C17 | 123.2 (3) |
C3—C4—H4 | 119.8 | C17—C16—H16 | 118.4 |
C3—C4—C5 | 120.3 (4) | C13—C17—H17 | 120.4 |
C5—C4—H4 | 119.8 | C16—C17—C13 | 119.1 (3) |
C4—C5—H5 | 120.3 | C16—C17—H17 | 120.4 |
C6—C5—C4 | 119.4 (3) | O2—N2—O3 | 119.9 |
C6—C5—H5 | 120.3 | O2—N2—O4 | 120.0 |
C5—C6—H6 | 119.5 | O4—N2—O3 | 120.1 |
C5—C6—C7 | 121.0 (3) | O3A—N2A—O2A | 120.1 |
C7—C6—H6 | 119.5 | O4A—N2A—O2A | 119.8 |
C2—C7—H7 | 120.0 | O4A—N2A—O3A | 120.0 |
Zn1—N1—C15—C14 | 178.9 (4) | C7—C2—C3—C4 | 1.0 (5) |
Zn1—N1—C16—C17 | −179.4 (3) | C8—C1—C2—C3 | −45.3 (4) |
S1—C10—C13—C14 | 174.1 (3) | C8—C1—C2—C7 | 132.9 (3) |
S1—C10—C13—C17 | −3.5 (5) | C8—C9—C10—S1 | −0.8 (4) |
N1—C16—C17—C13 | 0.9 (6) | C8—C9—C10—C13 | 174.8 (3) |
C1iv—C1—C2—C3 | 133.8 (4) | C9—C8—C11—S1 | 1.7 (4) |
C1iv—C1—C2—C7 | −48.0 (5) | C9—C8—C11—C12 | −176.9 (4) |
C1iv—C1—C8—C9 | −50.0 (5) | C9—C10—C13—C14 | −1.1 (6) |
C1iv—C1—C8—C11 | 131.5 (4) | C9—C10—C13—C17 | −178.7 (4) |
C1—C2—C3—C4 | 179.2 (3) | C10—S1—C11—C8 | −1.9 (3) |
C1—C2—C7—C6 | −179.0 (3) | C10—S1—C11—C12 | 176.9 (3) |
C1—C8—C9—C10 | −179.2 (3) | C10—C13—C14—C15 | −176.6 (4) |
C1—C8—C11—S1 | −179.7 (2) | C10—C13—C17—C16 | 176.1 (3) |
C1—C8—C11—C12 | 1.7 (6) | C11—S1—C10—C9 | 1.5 (3) |
C2—C1—C8—C9 | 129.1 (3) | C11—S1—C10—C13 | −174.4 (3) |
C2—C1—C8—C11 | −49.4 (4) | C11—C8—C9—C10 | −0.6 (4) |
C2—C3—C4—C5 | −0.7 (5) | C13—C14—C15—N1 | 0.1 (7) |
C3—C2—C7—C6 | −0.8 (4) | C14—C13—C17—C16 | −1.5 (6) |
C3—C4—C5—C6 | 0.2 (5) | C15—N1—C16—C17 | 0.3 (6) |
C4—C5—C6—C7 | −0.1 (5) | C16—N1—C15—C14 | −0.8 (7) |
C5—C6—C7—C2 | 0.4 (5) | C17—C13—C14—C15 | 1.1 (6) |
Symmetry codes: (i) −x+5/4, −y+5/4, z; (ii) −x+5/4, y, −z+5/4; (iii) x, −y+5/4, −z+5/4; (iv) −x+3/4, −y+3/4, z. |
C68H56CdN4O2S4·2(NO3) | Dx = 1.211 Mg m−3 |
Mr = 1325.82 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Fddd | Cell parameters from 9035 reflections |
a = 9.8116 (12) Å | θ = 2.2–28.2° |
b = 21.432 (3) Å | µ = 0.47 mm−1 |
c = 69.162 (8) Å | T = 90 K |
V = 14543 (3) Å3 | Prism, colourless |
Z = 8 | 0.14 × 0.14 × 0.02 mm |
F(000) = 5456 |
Bruker APEX-II CCD diffractometer | 4453 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.048 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1205 before and 0.0583 after correction. The Ratio of minimum to maximum transmission is 0.9130. The λ/2 correction factor is Not present. | θmax = 28.3°, θmin = 2.0° |
Tmin = 0.681, Tmax = 0.746 | h = −13→13 |
66341 measured reflections | k = −28→28 |
4548 independent reflections | l = −92→92 |
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.093 | H-atom parameters constrained |
wR(F2) = 0.233 | w = 1/[σ2(Fo2) + (0.0494P)2 + 496.5558P] where P = (Fo2 + 2Fc2)/3 |
S = 1.27 | (Δ/σ)max < 0.001 |
4548 reflections | Δρmax = 1.41 e Å−3 |
220 parameters | Δρmin = −0.86 e Å−3 |
47 restraints |
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) | |
Cd1 | 0.625000 | 0.125000 | 0.125000 | 0.0289 (2) | |
S1 | 0.69287 (16) | 0.38556 (8) | 0.19940 (2) | 0.0385 (4) | |
O1 | 0.3879 (9) | 0.125000 | 0.125000 | 0.060 (2) | |
H1A | 0.345510 | 0.106703 | 0.134500 | 0.091* | 0.5 |
H1B | 0.345405 | 0.112388 | 0.114670 | 0.091* | 0.5 |
N1 | 0.6058 (6) | 0.1998 (2) | 0.14891 (6) | 0.0333 (12) | |
C1 | 0.4439 (4) | 0.3743 (2) | 0.24506 (6) | 0.0160 (8) | |
C2 | 0.5264 (5) | 0.3780 (2) | 0.26316 (7) | 0.0201 (9) | |
C3 | 0.6344 (6) | 0.3366 (3) | 0.26614 (9) | 0.0321 (12) | |
H3 | 0.654196 | 0.305723 | 0.256678 | 0.038* | |
C4 | 0.7133 (7) | 0.3400 (3) | 0.28281 (10) | 0.0419 (17) | |
H4 | 0.786398 | 0.311593 | 0.284685 | 0.050* | |
C5 | 0.6857 (7) | 0.3847 (4) | 0.29666 (9) | 0.0443 (18) | |
H5 | 0.738763 | 0.386912 | 0.308126 | 0.053* | |
C6 | 0.5804 (7) | 0.4261 (3) | 0.29365 (8) | 0.0376 (16) | |
H6 | 0.561938 | 0.457264 | 0.303059 | 0.045* | |
C7 | 0.5007 (6) | 0.4230 (3) | 0.27710 (7) | 0.0264 (11) | |
H7 | 0.428271 | 0.451795 | 0.275313 | 0.032* | |
C8 | 0.5223 (5) | 0.3681 (2) | 0.22681 (7) | 0.0215 (10) | |
C9 | 0.4928 (5) | 0.3219 (2) | 0.21232 (6) | 0.0174 (9) | |
H9 | 0.421401 | 0.292155 | 0.213481 | 0.021* | |
C10 | 0.5782 (5) | 0.3250 (2) | 0.19664 (7) | 0.0213 (10) | |
C11 | 0.6308 (6) | 0.4049 (3) | 0.22176 (8) | 0.0284 (12) | |
C12 | 0.6965 (7) | 0.4562 (3) | 0.23306 (9) | 0.0419 (17) | |
H12A | 0.758008 | 0.438307 | 0.242747 | 0.063* | |
H12B | 0.626061 | 0.480976 | 0.239554 | 0.063* | |
H12C | 0.748531 | 0.483117 | 0.224286 | 0.063* | |
C13 | 0.5864 (5) | 0.2838 (2) | 0.17991 (7) | 0.0225 (10) | |
C14 | 0.4995 (7) | 0.2333 (3) | 0.17820 (9) | 0.0428 (18) | |
H14 | 0.431426 | 0.226395 | 0.187726 | 0.051* | |
C15 | 0.5111 (9) | 0.1926 (3) | 0.16264 (9) | 0.053 (2) | |
H15 | 0.449640 | 0.158443 | 0.161726 | 0.063* | |
C16 | 0.6890 (7) | 0.2480 (3) | 0.15051 (8) | 0.0346 (14) | |
H16 | 0.757387 | 0.253303 | 0.140926 | 0.042* | |
C17 | 0.6822 (7) | 0.2909 (3) | 0.16533 (9) | 0.0377 (15) | |
H17 | 0.743129 | 0.325387 | 0.165549 | 0.045* | |
O2 | 0.2336 (9) | 0.1657 (4) | 0.09506 (11) | 0.038 (2) | 0.5 |
O3 | 0.0886 (12) | 0.2175 (7) | 0.0788 (2) | 0.077 (4) | 0.5 |
O4 | 0.2339 (15) | 0.2642 (7) | 0.0966 (2) | 0.082 (4) | 0.5 |
N2 | 0.1828 (12) | 0.2153 (5) | 0.09059 (18) | 0.062 (3) | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.0568 (6) | 0.0216 (4) | 0.0083 (3) | 0.000 | 0.000 | 0.000 |
S1 | 0.0347 (8) | 0.0485 (9) | 0.0322 (7) | −0.0273 (7) | 0.0194 (6) | −0.0191 (6) |
O1 | 0.056 (5) | 0.099 (7) | 0.027 (3) | 0.000 | 0.000 | −0.007 (4) |
N1 | 0.050 (3) | 0.032 (2) | 0.0178 (19) | −0.009 (2) | 0.011 (2) | −0.0046 (18) |
C1 | 0.011 (2) | 0.022 (2) | 0.0151 (19) | −0.0053 (17) | −0.0002 (16) | −0.0012 (17) |
C2 | 0.020 (2) | 0.024 (2) | 0.0165 (19) | −0.0096 (19) | −0.0050 (18) | 0.0013 (18) |
C3 | 0.027 (3) | 0.029 (3) | 0.039 (3) | −0.009 (2) | −0.016 (3) | 0.005 (2) |
C4 | 0.036 (3) | 0.044 (4) | 0.046 (4) | −0.014 (3) | −0.026 (3) | 0.018 (3) |
C5 | 0.041 (4) | 0.065 (5) | 0.027 (3) | −0.031 (3) | −0.014 (3) | 0.017 (3) |
C6 | 0.039 (3) | 0.059 (4) | 0.015 (2) | −0.031 (3) | 0.005 (2) | −0.005 (2) |
C7 | 0.023 (3) | 0.038 (3) | 0.019 (2) | −0.014 (2) | 0.008 (2) | −0.004 (2) |
C8 | 0.021 (2) | 0.021 (2) | 0.023 (2) | −0.0045 (19) | −0.0016 (19) | −0.0060 (18) |
C9 | 0.014 (2) | 0.022 (2) | 0.016 (2) | −0.0049 (17) | 0.0007 (17) | −0.0007 (17) |
C10 | 0.020 (2) | 0.027 (2) | 0.017 (2) | −0.0083 (19) | 0.0031 (18) | −0.0033 (18) |
C11 | 0.020 (2) | 0.040 (3) | 0.026 (2) | −0.014 (2) | 0.008 (2) | −0.011 (2) |
C12 | 0.042 (4) | 0.049 (4) | 0.034 (3) | −0.033 (3) | 0.016 (3) | −0.022 (3) |
C13 | 0.023 (2) | 0.027 (2) | 0.017 (2) | −0.004 (2) | 0.0017 (19) | −0.0034 (18) |
C14 | 0.050 (4) | 0.053 (4) | 0.025 (3) | −0.033 (3) | 0.025 (3) | −0.016 (3) |
C15 | 0.079 (6) | 0.049 (4) | 0.030 (3) | −0.040 (4) | 0.029 (3) | −0.018 (3) |
C16 | 0.038 (3) | 0.040 (3) | 0.025 (3) | −0.014 (3) | 0.016 (2) | −0.011 (2) |
C17 | 0.035 (3) | 0.046 (3) | 0.032 (3) | −0.021 (3) | 0.018 (3) | −0.019 (3) |
O2 | 0.027 (4) | 0.065 (5) | 0.021 (4) | 0.010 (4) | 0.004 (3) | 0.018 (3) |
O3 | 0.051 (6) | 0.094 (9) | 0.084 (8) | 0.008 (6) | −0.030 (6) | 0.016 (7) |
O4 | 0.064 (8) | 0.092 (7) | 0.091 (9) | −0.001 (6) | −0.015 (7) | 0.004 (6) |
N2 | 0.039 (6) | 0.082 (6) | 0.064 (7) | 0.005 (5) | −0.015 (5) | 0.015 (5) |
Cd1—O1i | 2.327 (9) | C5—C6 | 1.377 (11) |
Cd1—O1 | 2.327 (9) | C6—H6 | 0.9500 |
Cd1—N1 | 2.311 (5) | C6—C7 | 1.387 (8) |
Cd1—N1ii | 2.311 (5) | C7—H7 | 0.9500 |
Cd1—N1i | 2.311 (5) | C8—C9 | 1.439 (6) |
Cd1—N1iii | 2.311 (5) | C8—C11 | 1.370 (7) |
S1—C10 | 1.728 (5) | C9—H9 | 0.9500 |
S1—C11 | 1.713 (5) | C9—C10 | 1.372 (6) |
O1—H1Aiii | 0.87 (8) | C10—C13 | 1.458 (7) |
O1—H1A | 0.8707 | C11—C12 | 1.496 (7) |
O1—H1B | 0.8701 | C12—H12A | 0.9800 |
O1—H1Biii | 0.87 (8) | C12—H12B | 0.9800 |
N1—C15 | 1.337 (8) | C12—H12C | 0.9800 |
N1—C16 | 1.321 (8) | C13—C14 | 1.383 (8) |
C1—C1iv | 1.352 (9) | C13—C17 | 1.387 (7) |
C1—C2 | 1.493 (6) | C14—H14 | 0.9500 |
C1—C8 | 1.484 (6) | C14—C15 | 1.391 (8) |
C2—C3 | 1.398 (8) | C15—H15 | 0.9500 |
C2—C7 | 1.387 (7) | C16—H16 | 0.9500 |
C3—H3 | 0.9500 | C16—C17 | 1.380 (8) |
C3—C4 | 1.391 (8) | C17—H17 | 0.9500 |
C4—H4 | 0.9500 | O2—N2 | 1.214 (10) |
C4—C5 | 1.381 (11) | O3—N2 | 1.235 (10) |
C5—H5 | 0.9500 | O4—N2 | 1.235 (11) |
O1i—Cd1—O1 | 180.0 | C6—C5—H5 | 120.4 |
N1iii—Cd1—O1i | 94.68 (15) | C5—C6—H6 | 119.5 |
N1iii—Cd1—O1 | 85.32 (15) | C5—C6—C7 | 121.1 (6) |
N1—Cd1—O1 | 85.32 (15) | C7—C6—H6 | 119.5 |
N1—Cd1—O1i | 94.68 (15) | C2—C7—C6 | 120.3 (6) |
N1ii—Cd1—O1i | 85.32 (15) | C2—C7—H7 | 119.8 |
N1ii—Cd1—O1 | 94.68 (15) | C6—C7—H7 | 119.8 |
N1i—Cd1—O1 | 94.68 (15) | C9—C8—C1 | 123.3 (4) |
N1i—Cd1—O1i | 85.32 (15) | C11—C8—C1 | 124.6 (4) |
N1iii—Cd1—N1 | 170.6 (3) | C11—C8—C9 | 112.0 (4) |
N1ii—Cd1—N1i | 170.6 (3) | C8—C9—H9 | 123.4 |
N1iii—Cd1—N1i | 92.2 (2) | C10—C9—C8 | 113.2 (4) |
N1ii—Cd1—N1 | 92.2 (2) | C10—C9—H9 | 123.4 |
N1i—Cd1—N1 | 88.6 (2) | C9—C10—S1 | 110.4 (4) |
N1iii—Cd1—N1ii | 88.6 (2) | C9—C10—C13 | 129.1 (5) |
C11—S1—C10 | 92.8 (2) | C13—C10—S1 | 120.4 (4) |
Cd1—O1—H1Aiii | 119 (3) | C8—C11—S1 | 111.5 (4) |
Cd1—O1—H1A | 118.5 | C8—C11—C12 | 128.7 (5) |
Cd1—O1—H1B | 118.6 | C12—C11—S1 | 119.7 (4) |
Cd1—O1—H1Biii | 119 (3) | C11—C12—H12A | 109.5 |
H1A—O1—H1Aiii | 123.0 | C11—C12—H12B | 109.5 |
H1Aiii—O1—H1Biii | 104.5 | C11—C12—H12C | 109.5 |
H1A—O1—H1Biii | 44.9 | H12A—C12—H12B | 109.5 |
H1A—O1—H1B | 104.5 | H12A—C12—H12C | 109.5 |
H1B—O1—H1Aiii | 44.9 | H12B—C12—H12C | 109.5 |
H1B—O1—H1Biii | 122.8 | C14—C13—C10 | 120.5 (5) |
C15—N1—Cd1 | 119.0 (4) | C14—C13—C17 | 116.2 (5) |
C16—N1—Cd1 | 123.5 (4) | C17—C13—C10 | 123.2 (5) |
C16—N1—C15 | 117.4 (5) | C13—C14—H14 | 119.8 |
C1iv—C1—C2 | 122.7 (3) | C13—C14—C15 | 120.5 (5) |
C1iv—C1—C8 | 121.4 (3) | C15—C14—H14 | 119.8 |
C8—C1—C2 | 115.9 (4) | N1—C15—C14 | 122.3 (6) |
C3—C2—C1 | 120.1 (5) | N1—C15—H15 | 118.9 |
C7—C2—C1 | 121.5 (5) | C14—C15—H15 | 118.9 |
C7—C2—C3 | 118.4 (5) | N1—C16—H16 | 118.2 |
C2—C3—H3 | 119.7 | N1—C16—C17 | 123.7 (5) |
C4—C3—C2 | 120.7 (6) | C17—C16—H16 | 118.2 |
C4—C3—H3 | 119.7 | C13—C17—H17 | 120.0 |
C3—C4—H4 | 119.9 | C16—C17—C13 | 120.0 (5) |
C5—C4—C3 | 120.2 (7) | C16—C17—H17 | 120.0 |
C5—C4—H4 | 119.9 | O2—N2—O3 | 120.6 (12) |
C4—C5—H5 | 120.4 | O2—N2—O4 | 119.3 (11) |
C6—C5—C4 | 119.3 (5) | O4—N2—O3 | 119.8 (12) |
Cd1—N1—C15—C14 | 175.5 (7) | C7—C2—C3—C4 | 0.7 (8) |
Cd1—N1—C16—C17 | −176.6 (6) | C8—C1—C2—C3 | −45.7 (7) |
S1—C10—C13—C14 | 176.5 (5) | C8—C1—C2—C7 | 132.6 (5) |
S1—C10—C13—C17 | −1.3 (8) | C8—C9—C10—S1 | −1.1 (6) |
N1—C16—C17—C13 | 1.8 (12) | C8—C9—C10—C13 | 175.1 (5) |
C1iv—C1—C2—C3 | 133.6 (7) | C9—C8—C11—S1 | 2.0 (6) |
C1iv—C1—C2—C7 | −48.0 (8) | C9—C8—C11—C12 | −177.5 (7) |
C1iv—C1—C8—C9 | −48.7 (9) | C9—C10—C13—C14 | 0.6 (9) |
C1iv—C1—C8—C11 | 131.7 (7) | C9—C10—C13—C17 | −177.2 (6) |
C1—C2—C3—C4 | 179.1 (5) | C10—S1—C11—C8 | −2.3 (5) |
C1—C2—C7—C6 | −178.9 (5) | C10—S1—C11—C12 | 177.3 (6) |
C1—C8—C9—C10 | 179.8 (5) | C10—C13—C14—C15 | −177.4 (7) |
C1—C8—C11—S1 | −178.3 (4) | C10—C13—C17—C16 | 176.2 (6) |
C1—C8—C11—C12 | 2.1 (11) | C11—S1—C10—C9 | 1.9 (5) |
C2—C1—C8—C9 | 130.7 (5) | C11—S1—C10—C13 | −174.7 (5) |
C2—C1—C8—C11 | −48.9 (7) | C11—C8—C9—C10 | −0.6 (7) |
C2—C3—C4—C5 | −0.1 (9) | C13—C14—C15—N1 | 0.6 (14) |
C3—C2—C7—C6 | −0.5 (8) | C14—C13—C17—C16 | −1.7 (10) |
C3—C4—C5—C6 | −0.7 (9) | C15—N1—C16—C17 | −0.7 (11) |
C4—C5—C6—C7 | 0.9 (9) | C16—N1—C15—C14 | −0.5 (13) |
C5—C6—C7—C2 | −0.3 (8) | C17—C13—C14—C15 | 0.5 (11) |
Symmetry codes: (i) −x+5/4, −y+1/4, z; (ii) −x+5/4, y, −z+1/4; (iii) x, −y+1/4, −z+1/4; (iv) −x+3/4, −y+3/4, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2iii | 0.87 | 1.85 | 2.709 (9) | 167 |
O1—H1B···O2 | 0.87 | 2.09 | 2.709 (9) | 128 |
Symmetry code: (iii) x, −y+1/4, −z+1/4. |
C34H26CuIN2S2·CH2Cl2 | Z = 2 |
Mr = 802.05 | F(000) = 800 |
Triclinic, P1 | Dx = 1.629 Mg m−3 |
a = 9.496 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.032 (3) Å | Cell parameters from 4741 reflections |
c = 17.380 (5) Å | θ = 2.2–26.4° |
α = 86.772 (8)° | µ = 1.93 mm−1 |
β = 84.163 (9)° | T = 90 K |
γ = 83.443 (9)° | Plate, yellow |
V = 1634.7 (8) Å3 | 0.14 × 0.06 × 0.01 mm |
Bruker APEX-II CCD diffractometer | 3988 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.070 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1372 before and 0.0661 after correction. The Ratio of minimum to maximum transmission is 0.7738. The λ/2 correction factor is Not present. | θmax = 24.7°, θmin = 2.1° |
Tmin = 0.577, Tmax = 0.745 | h = −11→11 |
15927 measured reflections | k = −11→11 |
5512 independent reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.139 | w = 1/[σ2(Fo2) + (0.0674P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
5512 reflections | Δρmax = 1.56 e Å−3 |
392 parameters | Δρmin = −0.99 e Å−3 |
0 restraints |
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 | ||
Cu1 | 0.41700 (9) | 0.12901 (8) | 0.50322 (5) | 0.0214 (2) | |
S1 | 0.62638 (19) | 0.49354 (18) | 0.82463 (11) | 0.0241 (4) | |
S2 | 0.03898 (18) | 0.63303 (17) | 0.81059 (11) | 0.0226 (4) | |
N1 | 0.4511 (6) | 0.2638 (6) | 0.5809 (3) | 0.0223 (14) | |
N2 | −0.2566 (6) | 0.8206 (6) | 0.5668 (3) | 0.0213 (13) | |
C1 | 0.4401 (7) | 0.8717 (6) | 0.8420 (4) | 0.0179 (15) | |
C2 | 0.5479 (7) | 0.9672 (6) | 0.8523 (4) | 0.0193 (16) | |
C3 | 0.6710 (7) | 0.9624 (7) | 0.8003 (4) | 0.0255 (17) | |
H3 | 0.685409 | 0.899801 | 0.760471 | 0.031* | |
C4 | 0.7724 (8) | 1.0503 (7) | 0.8075 (5) | 0.0292 (18) | |
H4 | 0.855406 | 1.047667 | 0.771916 | 0.035* | |
C5 | 0.7541 (8) | 1.1396 (7) | 0.8648 (4) | 0.0286 (18) | |
H5 | 0.825275 | 1.196981 | 0.869704 | 0.034* | |
C6 | 0.6326 (8) | 1.1468 (8) | 0.9156 (4) | 0.0303 (18) | |
H6 | 0.618760 | 1.210915 | 0.954599 | 0.036* | |
C7 | 0.5299 (8) | 1.0600 (7) | 0.9096 (4) | 0.0265 (17) | |
H7 | 0.446737 | 1.064514 | 0.945104 | 0.032* | |
C8 | 0.4977 (7) | 0.7322 (7) | 0.8211 (4) | 0.0203 (16) | |
C9 | 0.4569 (7) | 0.6683 (7) | 0.7574 (4) | 0.0198 (16) | |
H9 | 0.393938 | 0.711781 | 0.722425 | 0.024* | |
C10 | 0.5175 (7) | 0.5366 (6) | 0.7510 (4) | 0.0182 (15) | |
C11 | 0.5932 (7) | 0.6516 (7) | 0.8623 (4) | 0.0217 (16) | |
C12 | 0.6591 (8) | 0.6793 (8) | 0.9335 (4) | 0.037 (2) | |
H12A | 0.607 (4) | 0.655 (5) | 0.973 (2) | 0.056* | |
H12B | 0.667 (5) | 0.763 (4) | 0.9342 (16) | 0.056* | |
H12C | 0.741 (5) | 0.635 (5) | 0.9334 (16) | 0.056* | |
C13 | 0.4973 (7) | 0.4425 (7) | 0.6929 (4) | 0.0202 (16) | |
C14 | 0.4244 (8) | 0.4857 (7) | 0.6277 (4) | 0.0260 (17) | |
H14 | 0.389607 | 0.577705 | 0.620363 | 0.031* | |
C15 | 0.4037 (8) | 0.3959 (7) | 0.5751 (4) | 0.0241 (16) | |
H15 | 0.353276 | 0.427786 | 0.532028 | 0.029* | |
C16 | 0.5222 (8) | 0.2232 (7) | 0.6432 (4) | 0.0290 (18) | |
H16 | 0.557166 | 0.130904 | 0.648848 | 0.035* | |
C17 | 0.5468 (7) | 0.3075 (7) | 0.6987 (4) | 0.0219 (16) | |
H17 | 0.597887 | 0.273178 | 0.741046 | 0.026* | |
C18 | 0.2983 (7) | 0.9091 (6) | 0.8480 (4) | 0.0198 (16) | |
C19 | 0.2320 (7) | 1.0471 (7) | 0.8676 (4) | 0.0197 (16) | |
C20 | 0.1492 (7) | 1.0640 (7) | 0.9383 (4) | 0.0224 (16) | |
H20 | 0.137169 | 0.989456 | 0.973632 | 0.027* | |
C21 | 0.0845 (7) | 1.1919 (7) | 0.9562 (4) | 0.0272 (18) | |
H21 | 0.027938 | 1.204225 | 1.004167 | 0.033* | |
C22 | 0.1014 (8) | 1.3003 (7) | 0.9055 (4) | 0.0276 (18) | |
H22 | 0.057487 | 1.386882 | 0.918848 | 0.033* | |
C23 | 0.1818 (8) | 1.2839 (7) | 0.8354 (5) | 0.0315 (19) | |
H23 | 0.192170 | 1.358675 | 0.800031 | 0.038* | |
C24 | 0.2474 (8) | 1.1580 (7) | 0.8168 (4) | 0.0266 (18) | |
H24 | 0.303671 | 1.147018 | 0.768746 | 0.032* | |
C25 | 0.1915 (7) | 0.8223 (7) | 0.8281 (4) | 0.0183 (15) | |
C26 | 0.1106 (7) | 0.8616 (7) | 0.7637 (4) | 0.0207 (16) | |
H26 | 0.117277 | 0.944979 | 0.735521 | 0.025* | |
C27 | 0.0253 (7) | 0.7733 (7) | 0.7460 (4) | 0.0170 (15) | |
C28 | 0.1630 (7) | 0.6994 (7) | 0.8596 (4) | 0.0202 (16) | |
C29 | 0.2275 (7) | 0.6220 (7) | 0.9262 (4) | 0.0243 (17) | |
H29A | 0.159 (3) | 0.589 (4) | 0.9579 (19) | 0.036* | |
H29B | 0.272 (5) | 0.676 (2) | 0.9517 (19) | 0.036* | |
H29C | 0.289 (4) | 0.555 (4) | 0.9085 (8) | 0.036* | |
C30 | −0.0684 (7) | 0.7827 (7) | 0.6834 (4) | 0.0192 (16) | |
C31 | −0.0692 (7) | 0.8950 (7) | 0.6318 (4) | 0.0238 (17) | |
H31 | −0.005774 | 0.960588 | 0.635494 | 0.029* | |
C32 | −0.1636 (7) | 0.9097 (7) | 0.5750 (4) | 0.0239 (17) | |
H32 | −0.162658 | 0.986275 | 0.540341 | 0.029* | |
C33 | −0.2505 (8) | 0.7110 (7) | 0.6147 (4) | 0.0235 (17) | |
H33 | −0.311375 | 0.644368 | 0.608402 | 0.028* | |
C34 | −0.1598 (7) | 0.6900 (7) | 0.6730 (4) | 0.0221 (16) | |
H34 | −0.160943 | 0.611108 | 0.705839 | 0.027* | |
I1 | 0.65206 (5) | 0.08498 (5) | 0.41025 (3) | 0.02341 (16) | |
Cl1 | −0.0267 (4) | 0.2999 (3) | 0.67979 (17) | 0.0767 (9) | |
Cl2 | −0.1207 (3) | 0.3195 (3) | 0.52618 (17) | 0.0757 (9) | |
C35 | 0.0180 (12) | 0.3384 (12) | 0.5831 (6) | 0.073 (3) | |
H35A | 0.103798 | 0.278963 | 0.564521 | 0.088* | |
H35B | 0.041570 | 0.432213 | 0.576828 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0206 (5) | 0.0174 (5) | 0.0279 (5) | −0.0085 (4) | −0.0038 (4) | −0.0012 (4) |
S1 | 0.0274 (10) | 0.0137 (9) | 0.0327 (11) | −0.0040 (8) | −0.0081 (8) | −0.0016 (8) |
S2 | 0.0239 (9) | 0.0152 (9) | 0.0308 (10) | −0.0107 (8) | −0.0060 (8) | 0.0031 (8) |
N1 | 0.021 (3) | 0.016 (3) | 0.031 (4) | −0.006 (3) | −0.001 (3) | −0.001 (3) |
N2 | 0.022 (3) | 0.018 (3) | 0.026 (3) | −0.008 (3) | −0.005 (2) | 0.004 (3) |
C1 | 0.026 (4) | 0.009 (3) | 0.021 (4) | −0.012 (3) | −0.004 (3) | −0.001 (3) |
C2 | 0.020 (4) | 0.007 (3) | 0.032 (4) | −0.008 (3) | −0.006 (3) | 0.004 (3) |
C3 | 0.022 (4) | 0.013 (4) | 0.042 (5) | −0.003 (3) | −0.004 (3) | 0.000 (3) |
C4 | 0.021 (4) | 0.019 (4) | 0.048 (5) | −0.010 (3) | 0.000 (3) | 0.002 (4) |
C5 | 0.024 (4) | 0.021 (4) | 0.043 (5) | −0.013 (3) | −0.011 (3) | 0.005 (4) |
C6 | 0.032 (4) | 0.026 (4) | 0.037 (5) | −0.014 (4) | −0.010 (4) | 0.001 (4) |
C7 | 0.029 (4) | 0.023 (4) | 0.029 (4) | −0.009 (3) | −0.007 (3) | 0.000 (4) |
C8 | 0.022 (4) | 0.014 (4) | 0.028 (4) | −0.013 (3) | −0.001 (3) | −0.001 (3) |
C9 | 0.013 (3) | 0.016 (4) | 0.032 (4) | −0.009 (3) | 0.002 (3) | 0.004 (3) |
C10 | 0.015 (3) | 0.014 (4) | 0.027 (4) | −0.008 (3) | −0.001 (3) | 0.003 (3) |
C11 | 0.025 (4) | 0.011 (4) | 0.029 (4) | −0.002 (3) | −0.002 (3) | −0.004 (3) |
C12 | 0.045 (5) | 0.031 (5) | 0.038 (5) | −0.001 (4) | −0.016 (4) | −0.003 (4) |
C13 | 0.020 (4) | 0.019 (4) | 0.024 (4) | −0.012 (3) | −0.001 (3) | 0.001 (3) |
C14 | 0.035 (4) | 0.008 (4) | 0.035 (4) | −0.004 (3) | −0.006 (3) | 0.001 (3) |
C15 | 0.031 (4) | 0.016 (4) | 0.028 (4) | −0.007 (3) | −0.009 (3) | −0.003 (3) |
C16 | 0.032 (4) | 0.016 (4) | 0.039 (5) | −0.005 (3) | −0.002 (4) | −0.002 (4) |
C17 | 0.024 (4) | 0.011 (4) | 0.030 (4) | −0.003 (3) | −0.005 (3) | 0.002 (3) |
C18 | 0.024 (4) | 0.009 (3) | 0.028 (4) | −0.011 (3) | −0.004 (3) | 0.006 (3) |
C19 | 0.018 (4) | 0.015 (4) | 0.029 (4) | −0.009 (3) | −0.010 (3) | 0.003 (3) |
C20 | 0.021 (4) | 0.014 (4) | 0.033 (4) | −0.008 (3) | −0.002 (3) | 0.003 (3) |
C21 | 0.022 (4) | 0.024 (4) | 0.037 (5) | −0.008 (3) | 0.004 (3) | −0.009 (4) |
C22 | 0.028 (4) | 0.011 (4) | 0.045 (5) | −0.007 (3) | −0.001 (4) | −0.004 (4) |
C23 | 0.035 (5) | 0.014 (4) | 0.045 (5) | −0.007 (3) | −0.002 (4) | 0.009 (4) |
C24 | 0.029 (4) | 0.024 (4) | 0.028 (4) | −0.011 (3) | 0.001 (3) | 0.004 (4) |
C25 | 0.014 (3) | 0.015 (4) | 0.026 (4) | −0.004 (3) | 0.000 (3) | −0.003 (3) |
C26 | 0.019 (4) | 0.014 (4) | 0.028 (4) | −0.006 (3) | 0.007 (3) | 0.001 (3) |
C27 | 0.015 (3) | 0.013 (4) | 0.021 (4) | 0.004 (3) | −0.003 (3) | 0.005 (3) |
C28 | 0.016 (3) | 0.013 (4) | 0.033 (4) | −0.007 (3) | −0.001 (3) | 0.001 (3) |
C29 | 0.026 (4) | 0.016 (4) | 0.034 (4) | −0.015 (3) | −0.006 (3) | 0.002 (3) |
C30 | 0.013 (3) | 0.014 (4) | 0.030 (4) | 0.000 (3) | −0.003 (3) | 0.004 (3) |
C31 | 0.016 (4) | 0.022 (4) | 0.035 (4) | −0.012 (3) | −0.006 (3) | 0.005 (4) |
C32 | 0.023 (4) | 0.021 (4) | 0.029 (4) | −0.012 (3) | −0.002 (3) | 0.004 (3) |
C33 | 0.031 (4) | 0.012 (4) | 0.029 (4) | −0.011 (3) | 0.000 (3) | 0.000 (3) |
C34 | 0.022 (4) | 0.018 (4) | 0.027 (4) | −0.010 (3) | −0.002 (3) | 0.002 (3) |
I1 | 0.0195 (3) | 0.0195 (3) | 0.0308 (3) | −0.00610 (19) | 0.00027 (18) | 0.0063 (2) |
Cl1 | 0.103 (2) | 0.0653 (19) | 0.0638 (18) | −0.0224 (17) | −0.0087 (16) | 0.0052 (16) |
Cl2 | 0.0726 (19) | 0.089 (2) | 0.0688 (18) | −0.0239 (17) | −0.0066 (15) | −0.0052 (17) |
C35 | 0.078 (8) | 0.092 (9) | 0.053 (7) | −0.033 (7) | 0.013 (6) | −0.021 (6) |
Cu1—Cu1i | 2.8745 (18) | C14—C15 | 1.362 (10) |
Cu1—N1 | 2.038 (6) | C15—H15 | 0.9500 |
Cu1—N2ii | 2.047 (6) | C16—H16 | 0.9500 |
Cu1—I1i | 2.6567 (11) | C16—C17 | 1.372 (10) |
Cu1—I1 | 2.6287 (11) | C17—H17 | 0.9500 |
S1—C10 | 1.732 (7) | C18—C19 | 1.496 (9) |
S1—C11 | 1.733 (7) | C18—C25 | 1.488 (9) |
S2—C27 | 1.751 (6) | C19—C20 | 1.398 (10) |
S2—C28 | 1.732 (7) | C19—C24 | 1.392 (9) |
N1—C15 | 1.351 (8) | C20—H20 | 0.9500 |
N1—C16 | 1.353 (9) | C20—C21 | 1.396 (10) |
N2—C32 | 1.349 (8) | C21—H21 | 0.9500 |
N2—C33 | 1.340 (8) | C21—C22 | 1.374 (10) |
C1—C2 | 1.510 (9) | C22—H22 | 0.9500 |
C1—C8 | 1.495 (9) | C22—C23 | 1.379 (10) |
C1—C18 | 1.351 (9) | C23—H23 | 0.9500 |
C2—C3 | 1.401 (10) | C23—C24 | 1.383 (10) |
C2—C7 | 1.385 (10) | C24—H24 | 0.9500 |
C3—H3 | 0.9500 | C25—C26 | 1.432 (9) |
C3—C4 | 1.397 (10) | C25—C28 | 1.365 (9) |
C4—H4 | 0.9500 | C26—H26 | 0.9500 |
C4—C5 | 1.361 (11) | C26—C27 | 1.334 (9) |
C5—H5 | 0.9500 | C27—C30 | 1.467 (9) |
C5—C6 | 1.377 (10) | C28—C29 | 1.501 (9) |
C6—H6 | 0.9500 | C29—H29A | 0.89 (4) |
C6—C7 | 1.395 (10) | C29—H29B | 0.89 (4) |
C7—H7 | 0.9500 | C29—H29C | 0.89 (4) |
C8—C9 | 1.418 (10) | C30—C31 | 1.400 (9) |
C8—C11 | 1.374 (9) | C30—C34 | 1.374 (9) |
C9—H9 | 0.9500 | C31—H31 | 0.9500 |
C9—C10 | 1.385 (9) | C31—C32 | 1.390 (9) |
C10—C13 | 1.461 (9) | C32—H32 | 0.9500 |
C11—C12 | 1.494 (10) | C33—H33 | 0.9500 |
C12—H12A | 0.85 (4) | C33—C34 | 1.387 (9) |
C12—H12B | 0.85 (4) | C34—H34 | 0.9500 |
C12—H12C | 0.85 (4) | Cl1—C35 | 1.724 (10) |
C13—C14 | 1.410 (10) | Cl2—C35 | 1.758 (11) |
C13—C17 | 1.384 (9) | C35—H35A | 0.9900 |
C14—H14 | 0.9500 | C35—H35B | 0.9900 |
N1—Cu1—Cu1i | 120.65 (17) | C17—C16—H16 | 118.1 |
N1—Cu1—N2ii | 118.2 (2) | C13—C17—H17 | 120.0 |
N1—Cu1—I1 | 107.72 (16) | C16—C17—C13 | 120.1 (7) |
N1—Cu1—I1i | 104.50 (16) | C16—C17—H17 | 120.0 |
N2ii—Cu1—Cu1i | 121.07 (17) | C1—C18—C19 | 123.8 (6) |
N2ii—Cu1—I1i | 106.48 (15) | C1—C18—C25 | 123.8 (6) |
N2ii—Cu1—I1 | 106.12 (16) | C25—C18—C19 | 112.2 (6) |
I1—Cu1—I1i | 114.11 (4) | C20—C19—C18 | 118.7 (6) |
C10—S1—C11 | 93.0 (3) | C24—C19—C18 | 122.1 (6) |
C28—S2—C27 | 92.1 (3) | C24—C19—C20 | 119.2 (7) |
C15—N1—Cu1 | 123.4 (5) | C19—C20—H20 | 120.5 |
C15—N1—C16 | 116.1 (6) | C21—C20—C19 | 119.0 (6) |
C16—N1—Cu1 | 120.5 (5) | C21—C20—H20 | 120.5 |
C32—N2—Cu1ii | 119.5 (4) | C20—C21—H21 | 119.6 |
C33—N2—Cu1ii | 123.1 (5) | C22—C21—C20 | 120.9 (7) |
C33—N2—C32 | 116.6 (6) | C22—C21—H21 | 119.6 |
C8—C1—C2 | 116.6 (6) | C21—C22—H22 | 119.8 |
C18—C1—C2 | 122.9 (6) | C21—C22—C23 | 120.3 (7) |
C18—C1—C8 | 120.4 (6) | C23—C22—H22 | 119.8 |
C3—C2—C1 | 117.9 (6) | C22—C23—H23 | 120.2 |
C7—C2—C1 | 123.3 (6) | C22—C23—C24 | 119.6 (7) |
C7—C2—C3 | 118.8 (6) | C24—C23—H23 | 120.2 |
C2—C3—H3 | 120.3 | C19—C24—H24 | 119.5 |
C4—C3—C2 | 119.5 (7) | C23—C24—C19 | 121.0 (7) |
C4—C3—H3 | 120.3 | C23—C24—H24 | 119.5 |
C3—C4—H4 | 119.5 | C26—C25—C18 | 119.3 (6) |
C5—C4—C3 | 121.0 (7) | C28—C25—C18 | 129.0 (6) |
C5—C4—H4 | 119.5 | C28—C25—C26 | 111.5 (6) |
C4—C5—H5 | 119.9 | C25—C26—H26 | 122.3 |
C4—C5—C6 | 120.2 (7) | C27—C26—C25 | 115.5 (6) |
C6—C5—H5 | 119.9 | C27—C26—H26 | 122.3 |
C5—C6—H6 | 120.1 | C26—C27—S2 | 109.7 (5) |
C5—C6—C7 | 119.9 (8) | C26—C27—C30 | 128.7 (6) |
C7—C6—H6 | 120.1 | C30—C27—S2 | 121.7 (5) |
C2—C7—C6 | 120.6 (7) | C25—C28—S2 | 111.2 (5) |
C2—C7—H7 | 119.7 | C25—C28—C29 | 128.0 (6) |
C6—C7—H7 | 119.7 | C29—C28—S2 | 120.8 (5) |
C9—C8—C1 | 123.2 (6) | C28—C29—H29A | 109.5 |
C11—C8—C1 | 123.7 (6) | C28—C29—H29B | 109.5 |
C11—C8—C9 | 113.1 (6) | C28—C29—H29C | 109.5 |
C8—C9—H9 | 123.1 | H29A—C29—H29B | 109.5 |
C10—C9—C8 | 113.7 (6) | H29A—C29—H29C | 109.5 |
C10—C9—H9 | 123.1 | H29B—C29—H29C | 109.5 |
C9—C10—S1 | 109.7 (5) | C31—C30—C27 | 118.6 (6) |
C9—C10—C13 | 127.8 (6) | C34—C30—C27 | 124.3 (6) |
C13—C10—S1 | 122.5 (5) | C34—C30—C31 | 117.0 (6) |
C8—C11—S1 | 110.5 (5) | C30—C31—H31 | 120.3 |
C8—C11—C12 | 129.8 (7) | C32—C31—C30 | 119.4 (6) |
C12—C11—S1 | 119.6 (5) | C32—C31—H31 | 120.3 |
C11—C12—H12A | 109.5 | N2—C32—C31 | 123.3 (6) |
C11—C12—H12B | 109.5 | N2—C32—H32 | 118.4 |
C11—C12—H12C | 109.5 | C31—C32—H32 | 118.4 |
H12A—C12—H12B | 109.5 | N2—C33—H33 | 118.3 |
H12A—C12—H12C | 109.5 | N2—C33—C34 | 123.3 (7) |
H12B—C12—H12C | 109.5 | C34—C33—H33 | 118.3 |
C14—C13—C10 | 121.0 (6) | C30—C34—C33 | 120.3 (6) |
C17—C13—C10 | 122.6 (6) | C30—C34—H34 | 119.8 |
C17—C13—C14 | 116.4 (7) | C33—C34—H34 | 119.8 |
C13—C14—H14 | 119.9 | Cu1—I1—Cu1i | 65.89 (4) |
C15—C14—C13 | 120.2 (6) | Cl1—C35—Cl2 | 112.1 (6) |
C15—C14—H14 | 119.9 | Cl1—C35—H35A | 109.2 |
N1—C15—C14 | 123.5 (7) | Cl1—C35—H35B | 109.2 |
N1—C15—H15 | 118.3 | Cl2—C35—H35A | 109.2 |
C14—C15—H15 | 118.3 | Cl2—C35—H35B | 109.2 |
N1—C16—H16 | 118.1 | H35A—C35—H35B | 107.9 |
N1—C16—C17 | 123.8 (7) | ||
Cu1—N1—C15—C14 | 178.9 (5) | C11—S1—C10—C13 | 179.2 (5) |
Cu1—N1—C16—C17 | −178.7 (5) | C11—C8—C9—C10 | 2.0 (8) |
Cu1ii—N2—C32—C31 | 167.4 (6) | C13—C14—C15—N1 | −0.7 (11) |
Cu1ii—N2—C33—C34 | −166.6 (5) | C14—C13—C17—C16 | −0.9 (10) |
S1—C10—C13—C14 | −171.0 (5) | C15—N1—C16—C17 | 0.2 (10) |
S1—C10—C13—C17 | 9.4 (9) | C16—N1—C15—C14 | 0.0 (10) |
S2—C27—C30—C31 | −177.1 (5) | C17—C13—C14—C15 | 1.1 (10) |
S2—C27—C30—C34 | 4.9 (10) | C18—C1—C2—C3 | −137.2 (7) |
N1—C16—C17—C13 | 0.3 (11) | C18—C1—C2—C7 | 41.8 (10) |
N2—C33—C34—C30 | −1.0 (11) | C18—C1—C8—C9 | 49.3 (9) |
C1—C2—C3—C4 | 179.3 (6) | C18—C1—C8—C11 | −129.3 (7) |
C1—C2—C7—C6 | −179.2 (6) | C18—C19—C20—C21 | −178.6 (6) |
C1—C8—C9—C10 | −176.7 (6) | C18—C19—C24—C23 | 178.2 (7) |
C1—C8—C11—S1 | 176.0 (5) | C18—C25—C26—C27 | 175.0 (6) |
C1—C8—C11—C12 | 0.4 (11) | C18—C25—C28—S2 | −174.9 (6) |
C1—C18—C19—C20 | −112.9 (8) | C18—C25—C28—C29 | 3.6 (12) |
C1—C18—C19—C24 | 68.8 (10) | C19—C18—C25—C26 | 60.2 (8) |
C1—C18—C25—C26 | −114.0 (8) | C19—C18—C25—C28 | −125.1 (8) |
C1—C18—C25—C28 | 60.7 (11) | C19—C20—C21—C22 | −0.1 (11) |
C2—C1—C8—C9 | −128.2 (7) | C20—C19—C24—C23 | −0.1 (11) |
C2—C1—C8—C11 | 53.2 (9) | C20—C21—C22—C23 | 0.7 (11) |
C2—C1—C18—C19 | −1.9 (11) | C21—C22—C23—C24 | −1.0 (12) |
C2—C1—C18—C25 | 171.7 (6) | C22—C23—C24—C19 | 0.7 (12) |
C2—C3—C4—C5 | 0.7 (11) | C24—C19—C20—C21 | −0.2 (10) |
C3—C2—C7—C6 | −0.2 (10) | C25—C18—C19—C20 | 72.9 (8) |
C3—C4—C5—C6 | −1.7 (11) | C25—C18—C19—C24 | −105.4 (7) |
C4—C5—C6—C7 | 1.7 (11) | C25—C26—C27—S2 | 0.7 (8) |
C5—C6—C7—C2 | −0.8 (11) | C25—C26—C27—C30 | −179.0 (6) |
C7—C2—C3—C4 | 0.3 (10) | C26—C25—C28—S2 | 0.2 (8) |
C8—C1—C2—C3 | 40.2 (9) | C26—C25—C28—C29 | 178.6 (6) |
C8—C1—C2—C7 | −140.8 (7) | C26—C27—C30—C31 | 2.5 (11) |
C8—C1—C18—C19 | −179.2 (6) | C26—C27—C30—C34 | −175.4 (7) |
C8—C1—C18—C25 | −5.6 (10) | C27—S2—C28—C25 | 0.2 (6) |
C8—C9—C10—S1 | −0.4 (7) | C27—S2—C28—C29 | −178.4 (6) |
C8—C9—C10—C13 | 179.5 (6) | C27—C30—C31—C32 | −176.1 (6) |
C9—C8—C11—S1 | −2.7 (7) | C27—C30—C34—C33 | 176.3 (6) |
C9—C8—C11—C12 | −178.4 (7) | C28—S2—C27—C26 | −0.5 (5) |
C9—C10—C13—C14 | 9.2 (10) | C28—S2—C27—C30 | 179.2 (6) |
C9—C10—C13—C17 | −170.4 (6) | C28—C25—C26—C27 | −0.6 (9) |
C10—S1—C11—C8 | 2.2 (5) | C30—C31—C32—N2 | 0.2 (11) |
C10—S1—C11—C12 | 178.3 (6) | C31—C30—C34—C33 | −1.7 (10) |
C10—C13—C14—C15 | −178.5 (6) | C32—N2—C33—C34 | 3.2 (10) |
C10—C13—C17—C16 | 178.7 (6) | C33—N2—C32—C31 | −2.8 (10) |
C11—S1—C10—C9 | −1.0 (5) | C34—C30—C31—C32 | 2.0 (10) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1. |
2(Br)·C68H52CuN4S4·2(C3H7NO) | Z = 1 |
Mr = 1422.92 | F(000) = 731 |
Triclinic, P1 | Dx = 1.450 Mg m−3 |
a = 9.5108 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.4444 (3) Å | Cell parameters from 9970 reflections |
c = 16.0164 (4) Å | θ = 2.2–32.6° |
α = 105.012 (1)° | µ = 1.74 mm−1 |
β = 98.452 (1)° | T = 90 K |
γ = 99.178 (1)° | Prism, green |
V = 1629.52 (8) Å3 | 0.6 × 0.4 × 0.4 mm |
Bruker APEX-II CCD diffractometer | 10164 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.033 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0610 before and 0.0371 after correction. The Ratio of minimum to maximum transmission is 0.9672. The λ/2 correction factor is Not present. | θmax = 33.2°, θmin = 1.3° |
Tmin = 0.722, Tmax = 0.747 | h = −14→14 |
44606 measured reflections | k = −17→17 |
12487 independent reflections | l = −24→24 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0605P)2 + 1.0289P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
12487 reflections | Δρmax = 1.70 e Å−3 |
454 parameters | Δρmin = −0.71 e Å−3 |
114 restraints |
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) | |
Br1 | 1.26812 (2) | 1.09682 (2) | 0.93183 (2) | 0.02182 (5) | |
Cu1 | 1.000000 | 1.000000 | 1.000000 | 0.03601 (11) | |
S1 | 0.96817 (4) | 0.46780 (4) | 0.62045 (3) | 0.01741 (8) | |
S2 | 0.43320 (5) | 0.25264 (4) | 0.77153 (3) | 0.01920 (9) | |
N1 | 0.94929 (18) | 0.84729 (14) | 0.89428 (10) | 0.0205 (3) | |
N2 | 0.87185 (19) | 0.08508 (14) | 0.92772 (11) | 0.0232 (3) | |
C1 | 0.57174 (18) | 0.28120 (15) | 0.48854 (11) | 0.0142 (3) | |
C2 | 0.57197 (18) | 0.26634 (16) | 0.39349 (11) | 0.0165 (3) | |
C3 | 0.61145 (18) | 0.37089 (17) | 0.36559 (11) | 0.0183 (3) | |
H3 | 0.629937 | 0.450804 | 0.406616 | 0.022* | |
C4 | 0.6240 (2) | 0.3593 (2) | 0.27840 (13) | 0.0274 (4) | |
H4 | 0.649004 | 0.431005 | 0.259833 | 0.033* | |
C5 | 0.5998 (2) | 0.2425 (3) | 0.21874 (14) | 0.0371 (6) | |
H5 | 0.608234 | 0.234206 | 0.159212 | 0.044* | |
C6 | 0.5635 (2) | 0.1381 (2) | 0.24572 (14) | 0.0347 (5) | |
H6 | 0.549317 | 0.058347 | 0.205010 | 0.042* | |
C7 | 0.5477 (2) | 0.14946 (19) | 0.33232 (13) | 0.0249 (4) | |
H7 | 0.520267 | 0.077413 | 0.350024 | 0.030* | |
C8 | 0.70294 (17) | 0.36501 (15) | 0.54958 (11) | 0.0138 (3) | |
C9 | 0.70041 (17) | 0.46077 (15) | 0.62616 (11) | 0.0145 (3) | |
H9 | 0.613163 | 0.477974 | 0.644077 | 0.017* | |
C10 | 0.83605 (18) | 0.52595 (15) | 0.67171 (11) | 0.0145 (3) | |
C11 | 0.84313 (18) | 0.35911 (15) | 0.53724 (11) | 0.0150 (3) | |
C12 | 0.8940 (2) | 0.27403 (17) | 0.46572 (12) | 0.0201 (3) | |
H12A | 0.996213 | 0.272953 | 0.485559 | 0.030* | |
H12B | 0.884138 | 0.302917 | 0.413062 | 0.030* | |
H12C | 0.835199 | 0.190389 | 0.451598 | 0.030* | |
C13 | 0.87406 (18) | 0.63311 (15) | 0.74959 (11) | 0.0154 (3) | |
C14 | 0.7685 (2) | 0.68727 (17) | 0.78751 (12) | 0.0208 (3) | |
H14 | 0.668407 | 0.652009 | 0.764363 | 0.025* | |
C15 | 0.8097 (2) | 0.79243 (18) | 0.85887 (12) | 0.0220 (3) | |
H15 | 0.735991 | 0.827453 | 0.883985 | 0.026* | |
C16 | 1.0501 (2) | 0.79594 (19) | 0.85792 (16) | 0.0319 (5) | |
H16 | 1.149286 | 0.834281 | 0.881561 | 0.038* | |
C17 | 1.0183 (2) | 0.69009 (18) | 0.78780 (15) | 0.0284 (4) | |
H17 | 1.094681 | 0.655950 | 0.765489 | 0.034* | |
C18 | 0.46344 (18) | 0.22396 (15) | 0.52011 (11) | 0.0146 (3) | |
C19 | 0.32182 (18) | 0.15034 (15) | 0.46354 (11) | 0.0153 (3) | |
C20 | 0.2579 (2) | 0.04041 (16) | 0.47798 (12) | 0.0195 (3) | |
H20 | 0.307148 | 0.011491 | 0.522131 | 0.023* | |
C21 | 0.1234 (2) | −0.02710 (17) | 0.42876 (13) | 0.0221 (3) | |
H21 | 0.081628 | −0.101708 | 0.439353 | 0.027* | |
C22 | 0.0498 (2) | 0.01399 (18) | 0.36408 (12) | 0.0217 (3) | |
H22 | −0.042448 | −0.031914 | 0.330581 | 0.026* | |
C23 | 0.1121 (2) | 0.12233 (18) | 0.34892 (12) | 0.0205 (3) | |
H23 | 0.062757 | 0.150382 | 0.304290 | 0.025* | |
C24 | 0.24641 (19) | 0.19057 (16) | 0.39849 (11) | 0.0178 (3) | |
H24 | 0.287272 | 0.265467 | 0.387929 | 0.021* | |
C25 | 0.48125 (18) | 0.22983 (15) | 0.61492 (11) | 0.0146 (3) | |
C26 | 0.60321 (18) | 0.20203 (16) | 0.66357 (11) | 0.0160 (3) | |
H26 | 0.683733 | 0.180372 | 0.638929 | 0.019* | |
C27 | 0.59324 (18) | 0.20952 (16) | 0.74941 (11) | 0.0167 (3) | |
C28 | 0.37956 (18) | 0.25947 (16) | 0.66595 (11) | 0.0164 (3) | |
C29 | 0.23763 (19) | 0.29405 (19) | 0.64078 (13) | 0.0223 (3) | |
H29A | 0.207764 | 0.338707 | 0.694006 | 0.033* | |
H29B | 0.163797 | 0.219033 | 0.609906 | 0.033* | |
H29C | 0.248280 | 0.347084 | 0.601929 | 0.033* | |
C30 | 0.69144 (19) | 0.17605 (16) | 0.81459 (11) | 0.0176 (3) | |
C31 | 0.8321 (2) | 0.1653 (2) | 0.80416 (14) | 0.0304 (5) | |
H31 | 0.870102 | 0.189393 | 0.758103 | 0.037* | |
C32 | 0.9164 (3) | 0.1194 (2) | 0.86112 (14) | 0.0346 (5) | |
H32 | 1.011512 | 0.112090 | 0.852108 | 0.041* | |
C33 | 0.7384 (2) | 0.10256 (19) | 0.94116 (14) | 0.0269 (4) | |
H33 | 0.705351 | 0.082289 | 0.989833 | 0.032* | |
C34 | 0.6476 (2) | 0.14846 (19) | 0.88755 (13) | 0.0239 (4) | |
H34 | 0.555949 | 0.161009 | 0.900589 | 0.029* | |
O1A | 1.1906 (10) | 0.4693 (8) | 0.8340 (6) | 0.0450 (15) | 0.5 |
N3A | 1.1093 (6) | 0.4637 (4) | 0.9561 (3) | 0.0399 (10) | 0.5 |
C35A | 1.1751 (7) | 0.4216 (6) | 0.8899 (4) | 0.0396 (13) | 0.5 |
H35A | 1.211734 | 0.348514 | 0.887643 | 0.048* | 0.5 |
C36A | 1.0406 (12) | 0.5683 (8) | 0.9609 (5) | 0.079 (3) | 0.5 |
H36D | 0.934895 | 0.539349 | 0.944914 | 0.118* | 0.5 |
H36F | 1.073117 | 0.612330 | 0.920020 | 0.118* | 0.5 |
H36E | 1.067181 | 0.624168 | 1.021157 | 0.118* | 0.5 |
C37A | 1.0996 (18) | 0.4102 (11) | 1.0261 (7) | 0.152 (7) | 0.5 |
H37D | 1.184061 | 0.373098 | 1.036479 | 0.229* | 0.5 |
H37E | 1.010539 | 0.346281 | 1.010589 | 0.229* | 0.5 |
H37F | 1.097318 | 0.474361 | 1.079756 | 0.229* | 0.5 |
O1 | 0.1890 (18) | 0.4560 (15) | 0.8406 (9) | 0.103 (4) | 0.5 |
N3 | 0.3716 (7) | 0.4854 (4) | 0.9633 (3) | 0.0571 (14) | 0.5 |
C35 | 0.2469 (9) | 0.4302 (7) | 0.9054 (4) | 0.0509 (16) | 0.5 |
H35 | 0.194721 | 0.359486 | 0.916298 | 0.061* | 0.5 |
C36 | 0.4320 (12) | 0.4304 (7) | 1.0283 (5) | 0.076 (3) | 0.5 |
H36A | 0.526858 | 0.413802 | 1.017957 | 0.114* | 0.5 |
H36B | 0.366367 | 0.352667 | 1.023654 | 0.114* | 0.5 |
H36C | 0.443572 | 0.487331 | 1.087452 | 0.114* | 0.5 |
C37 | 0.4598 (16) | 0.5940 (9) | 0.9524 (7) | 0.120 (5) | 0.5 |
H37A | 0.396539 | 0.645761 | 0.933278 | 0.180* | 0.5 |
H37B | 0.518003 | 0.568429 | 0.907879 | 0.180* | 0.5 |
H37C | 0.524361 | 0.641116 | 1.008667 | 0.180* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02189 (9) | 0.02427 (9) | 0.02463 (10) | 0.00732 (7) | 0.00833 (7) | 0.01267 (7) |
Cu1 | 0.0571 (3) | 0.01749 (15) | 0.01914 (16) | 0.02099 (16) | −0.02692 (16) | −0.00833 (12) |
S1 | 0.01262 (17) | 0.01780 (18) | 0.01790 (19) | 0.00236 (14) | −0.00044 (14) | 0.00077 (14) |
S2 | 0.01721 (18) | 0.0278 (2) | 0.01523 (18) | 0.00785 (16) | 0.00166 (14) | 0.00976 (16) |
N1 | 0.0270 (8) | 0.0154 (6) | 0.0130 (6) | 0.0064 (6) | −0.0095 (5) | −0.0001 (5) |
N2 | 0.0298 (8) | 0.0162 (7) | 0.0172 (7) | 0.0082 (6) | −0.0103 (6) | −0.0002 (5) |
C1 | 0.0155 (7) | 0.0123 (6) | 0.0126 (6) | 0.0022 (5) | −0.0009 (5) | 0.0021 (5) |
C2 | 0.0136 (7) | 0.0189 (7) | 0.0139 (7) | 0.0021 (6) | 0.0008 (5) | 0.0011 (6) |
C3 | 0.0152 (7) | 0.0238 (8) | 0.0144 (7) | 0.0014 (6) | 0.0010 (6) | 0.0059 (6) |
C4 | 0.0176 (8) | 0.0437 (12) | 0.0179 (8) | −0.0034 (8) | 0.0028 (6) | 0.0101 (8) |
C5 | 0.0225 (9) | 0.0626 (16) | 0.0151 (8) | −0.0055 (10) | 0.0071 (7) | −0.0011 (9) |
C6 | 0.0261 (10) | 0.0416 (12) | 0.0213 (9) | −0.0041 (9) | 0.0067 (8) | −0.0113 (8) |
C7 | 0.0217 (8) | 0.0225 (8) | 0.0220 (9) | −0.0007 (7) | 0.0034 (7) | −0.0047 (7) |
C8 | 0.0139 (6) | 0.0124 (6) | 0.0132 (6) | 0.0013 (5) | −0.0007 (5) | 0.0032 (5) |
C9 | 0.0133 (7) | 0.0131 (6) | 0.0145 (7) | 0.0023 (5) | −0.0002 (5) | 0.0016 (5) |
C10 | 0.0143 (7) | 0.0132 (6) | 0.0143 (7) | 0.0026 (5) | −0.0002 (5) | 0.0026 (5) |
C11 | 0.0155 (7) | 0.0146 (7) | 0.0132 (7) | 0.0029 (5) | −0.0001 (5) | 0.0028 (5) |
C12 | 0.0185 (8) | 0.0211 (8) | 0.0189 (8) | 0.0056 (6) | 0.0029 (6) | 0.0022 (6) |
C13 | 0.0155 (7) | 0.0126 (6) | 0.0150 (7) | 0.0015 (5) | −0.0031 (5) | 0.0029 (5) |
C14 | 0.0189 (8) | 0.0214 (8) | 0.0163 (8) | −0.0020 (6) | 0.0032 (6) | −0.0006 (6) |
C15 | 0.0260 (9) | 0.0210 (8) | 0.0149 (7) | 0.0016 (7) | 0.0043 (6) | −0.0001 (6) |
C16 | 0.0220 (9) | 0.0194 (9) | 0.0383 (12) | 0.0068 (7) | −0.0153 (8) | −0.0091 (8) |
C17 | 0.0167 (8) | 0.0206 (8) | 0.0357 (11) | 0.0070 (7) | −0.0081 (7) | −0.0077 (8) |
C18 | 0.0151 (7) | 0.0133 (6) | 0.0137 (7) | 0.0019 (5) | −0.0022 (5) | 0.0043 (5) |
C19 | 0.0155 (7) | 0.0146 (7) | 0.0139 (7) | 0.0008 (5) | −0.0006 (5) | 0.0043 (5) |
C20 | 0.0207 (8) | 0.0178 (7) | 0.0180 (8) | −0.0004 (6) | −0.0013 (6) | 0.0071 (6) |
C21 | 0.0216 (8) | 0.0189 (8) | 0.0223 (8) | −0.0038 (6) | 0.0007 (7) | 0.0066 (6) |
C22 | 0.0185 (8) | 0.0232 (8) | 0.0184 (8) | −0.0021 (6) | −0.0014 (6) | 0.0039 (6) |
C23 | 0.0182 (8) | 0.0254 (8) | 0.0154 (7) | 0.0009 (6) | −0.0030 (6) | 0.0071 (6) |
C24 | 0.0174 (7) | 0.0191 (7) | 0.0161 (7) | 0.0005 (6) | −0.0006 (6) | 0.0078 (6) |
C25 | 0.0158 (7) | 0.0137 (6) | 0.0129 (7) | 0.0014 (5) | −0.0014 (5) | 0.0049 (5) |
C26 | 0.0157 (7) | 0.0169 (7) | 0.0147 (7) | 0.0040 (6) | −0.0005 (5) | 0.0048 (6) |
C27 | 0.0159 (7) | 0.0196 (7) | 0.0155 (7) | 0.0056 (6) | 0.0005 (6) | 0.0069 (6) |
C28 | 0.0145 (7) | 0.0198 (7) | 0.0155 (7) | 0.0027 (6) | −0.0012 (5) | 0.0088 (6) |
C29 | 0.0157 (7) | 0.0304 (9) | 0.0230 (8) | 0.0070 (7) | −0.0001 (6) | 0.0125 (7) |
C30 | 0.0183 (7) | 0.0189 (7) | 0.0145 (7) | 0.0052 (6) | −0.0015 (6) | 0.0047 (6) |
C31 | 0.0274 (10) | 0.0507 (13) | 0.0205 (9) | 0.0230 (9) | 0.0050 (7) | 0.0137 (9) |
C32 | 0.0316 (11) | 0.0548 (14) | 0.0208 (9) | 0.0286 (10) | −0.0004 (8) | 0.0081 (9) |
C33 | 0.0268 (9) | 0.0264 (9) | 0.0256 (9) | 0.0000 (7) | −0.0081 (7) | 0.0151 (8) |
C34 | 0.0182 (8) | 0.0293 (9) | 0.0256 (9) | 0.0027 (7) | −0.0030 (7) | 0.0159 (8) |
O1A | 0.065 (4) | 0.051 (3) | 0.045 (3) | 0.035 (3) | 0.038 (3) | 0.029 (3) |
N3A | 0.070 (3) | 0.034 (2) | 0.0298 (19) | 0.022 (2) | 0.0243 (19) | 0.0198 (16) |
C35A | 0.054 (4) | 0.036 (3) | 0.034 (3) | 0.012 (3) | 0.016 (3) | 0.014 (2) |
C36A | 0.135 (8) | 0.080 (5) | 0.065 (4) | 0.069 (5) | 0.062 (5) | 0.046 (4) |
C37A | 0.333 (18) | 0.139 (9) | 0.105 (7) | 0.169 (11) | 0.155 (10) | 0.108 (7) |
O1 | 0.130 (9) | 0.134 (10) | 0.080 (6) | 0.069 (7) | 0.029 (5) | 0.062 (6) |
N3 | 0.112 (4) | 0.0250 (19) | 0.031 (2) | 0.007 (2) | 0.013 (2) | 0.0079 (16) |
C35 | 0.079 (4) | 0.047 (3) | 0.037 (3) | 0.029 (3) | 0.030 (3) | 0.009 (2) |
C36 | 0.122 (7) | 0.034 (3) | 0.055 (4) | −0.016 (4) | −0.013 (4) | 0.019 (3) |
C37 | 0.195 (11) | 0.066 (5) | 0.069 (6) | −0.049 (7) | −0.017 (7) | 0.036 (5) |
Cu1—N1 | 2.0278 (15) | C20—C21 | 1.388 (2) |
Cu1—N1i | 2.0278 (15) | C21—H21 | 0.9500 |
Cu1—N2ii | 2.0789 (15) | C21—C22 | 1.389 (3) |
Cu1—N2iii | 2.0789 (15) | C22—H22 | 0.9500 |
S1—C10 | 1.7271 (17) | C22—C23 | 1.382 (3) |
S1—C11 | 1.7150 (17) | C23—H23 | 0.9500 |
S2—C27 | 1.7301 (18) | C23—C24 | 1.391 (2) |
S2—C28 | 1.7186 (17) | C24—H24 | 0.9500 |
N1—C15 | 1.344 (2) | C25—C26 | 1.426 (2) |
N1—C16 | 1.331 (3) | C25—C28 | 1.383 (2) |
N2—C32 | 1.330 (3) | C26—H26 | 0.9500 |
N2—C33 | 1.355 (3) | C26—C27 | 1.373 (2) |
C1—C2 | 1.488 (2) | C27—C30 | 1.464 (2) |
C1—C8 | 1.485 (2) | C28—C29 | 1.495 (2) |
C1—C18 | 1.362 (2) | C29—H29A | 0.9800 |
C2—C3 | 1.398 (2) | C29—H29B | 0.9800 |
C2—C7 | 1.399 (2) | C29—H29C | 0.9800 |
C3—H3 | 0.9500 | C30—C31 | 1.393 (3) |
C3—C4 | 1.393 (3) | C30—C34 | 1.390 (3) |
C4—H4 | 0.9500 | C31—H31 | 0.9500 |
C4—C5 | 1.389 (3) | C31—C32 | 1.385 (3) |
C5—H5 | 0.9500 | C32—H32 | 0.9500 |
C5—C6 | 1.383 (4) | C33—H33 | 0.9500 |
C6—H6 | 0.9500 | C33—C34 | 1.385 (3) |
C6—C7 | 1.392 (3) | C34—H34 | 0.9500 |
C7—H7 | 0.9500 | O1A—C35A | 1.178 (9) |
C8—C9 | 1.424 (2) | N3A—C35A | 1.332 (7) |
C8—C11 | 1.386 (2) | N3A—C36A | 1.443 (7) |
C9—H9 | 0.9500 | N3A—C37A | 1.417 (7) |
C9—C10 | 1.374 (2) | C35A—H35A | 0.9500 |
C10—C13 | 1.457 (2) | C36A—H36D | 0.9800 |
C11—C12 | 1.493 (2) | C36A—H36F | 0.9800 |
C12—H12A | 0.9800 | C36A—H36E | 0.9800 |
C12—H12B | 0.9800 | C37A—H37D | 0.9800 |
C12—H12C | 0.9800 | C37A—H37E | 0.9800 |
C13—C14 | 1.394 (3) | C37A—H37F | 0.9800 |
C13—C17 | 1.394 (2) | O1—C35 | 1.230 (13) |
C14—H14 | 0.9500 | N3—C35 | 1.342 (9) |
C14—C15 | 1.383 (2) | N3—C36 | 1.446 (8) |
C15—H15 | 0.9500 | N3—C37 | 1.449 (8) |
C16—H16 | 0.9500 | C35—H35 | 0.9500 |
C16—C17 | 1.378 (3) | C36—H36A | 0.9800 |
C17—H17 | 0.9500 | C36—H36B | 0.9800 |
C18—C19 | 1.493 (2) | C36—H36C | 0.9800 |
C18—C25 | 1.486 (2) | C37—H37A | 0.9800 |
C19—C20 | 1.398 (2) | C37—H37B | 0.9800 |
C19—C24 | 1.395 (2) | C37—H37C | 0.9800 |
C20—H20 | 0.9500 | ||
N1—Cu1—N1i | 180.00 (7) | C22—C21—H21 | 119.9 |
N1—Cu1—N2ii | 88.65 (6) | C21—C22—H22 | 120.3 |
N1i—Cu1—N2ii | 91.35 (6) | C23—C22—C21 | 119.37 (16) |
N1i—Cu1—N2iii | 88.65 (6) | C23—C22—H22 | 120.3 |
N1—Cu1—N2iii | 91.35 (6) | C22—C23—H23 | 119.7 |
N2iii—Cu1—N2ii | 180.0 | C22—C23—C24 | 120.51 (16) |
C11—S1—C10 | 93.08 (8) | C24—C23—H23 | 119.7 |
C28—S2—C27 | 92.55 (8) | C19—C24—H24 | 119.6 |
C15—N1—Cu1 | 120.34 (13) | C23—C24—C19 | 120.78 (16) |
C16—N1—Cu1 | 122.47 (13) | C23—C24—H24 | 119.6 |
C16—N1—C15 | 117.18 (16) | C26—C25—C18 | 124.10 (15) |
C32—N2—Cu1iv | 119.94 (14) | C28—C25—C18 | 124.02 (15) |
C32—N2—C33 | 116.41 (16) | C28—C25—C26 | 111.86 (15) |
C33—N2—Cu1iv | 123.55 (14) | C25—C26—H26 | 123.2 |
C8—C1—C2 | 114.47 (14) | C27—C26—C25 | 113.65 (15) |
C18—C1—C2 | 124.74 (15) | C27—C26—H26 | 123.2 |
C18—C1—C8 | 120.79 (15) | C26—C27—S2 | 110.47 (12) |
C3—C2—C1 | 119.47 (15) | C26—C27—C30 | 127.87 (16) |
C3—C2—C7 | 118.63 (17) | C30—C27—S2 | 121.42 (13) |
C7—C2—C1 | 121.59 (16) | C25—C28—S2 | 111.47 (12) |
C2—C3—H3 | 119.6 | C25—C28—C29 | 129.01 (15) |
C4—C3—C2 | 120.83 (18) | C29—C28—S2 | 119.53 (13) |
C4—C3—H3 | 119.6 | C28—C29—H29A | 109.5 |
C3—C4—H4 | 120.2 | C28—C29—H29B | 109.5 |
C5—C4—C3 | 119.6 (2) | C28—C29—H29C | 109.5 |
C5—C4—H4 | 120.2 | H29A—C29—H29B | 109.5 |
C4—C5—H5 | 119.9 | H29A—C29—H29C | 109.5 |
C6—C5—C4 | 120.22 (19) | H29B—C29—H29C | 109.5 |
C6—C5—H5 | 119.9 | C31—C30—C27 | 121.20 (17) |
C5—C6—H6 | 119.9 | C34—C30—C27 | 122.00 (16) |
C5—C6—C7 | 120.2 (2) | C34—C30—C31 | 116.75 (17) |
C7—C6—H6 | 119.9 | C30—C31—H31 | 120.1 |
C2—C7—H7 | 119.8 | C32—C31—C30 | 119.8 (2) |
C6—C7—C2 | 120.4 (2) | C32—C31—H31 | 120.1 |
C6—C7—H7 | 119.8 | N2—C32—C31 | 123.8 (2) |
C9—C8—C1 | 124.64 (15) | N2—C32—H32 | 118.1 |
C11—C8—C1 | 123.16 (15) | C31—C32—H32 | 118.1 |
C11—C8—C9 | 112.20 (14) | N2—C33—H33 | 118.3 |
C8—C9—H9 | 123.2 | N2—C33—C34 | 123.3 (2) |
C10—C9—C8 | 113.65 (15) | C34—C33—H33 | 118.3 |
C10—C9—H9 | 123.2 | C30—C34—H34 | 120.2 |
C9—C10—S1 | 110.18 (12) | C33—C34—C30 | 119.64 (19) |
C9—C10—C13 | 128.55 (16) | C33—C34—H34 | 120.2 |
C13—C10—S1 | 121.21 (12) | C35A—N3A—C36A | 121.6 (5) |
C8—C11—S1 | 110.87 (12) | C35A—N3A—C37A | 123.6 (6) |
C8—C11—C12 | 129.58 (15) | C37A—N3A—C36A | 114.8 (5) |
C12—C11—S1 | 119.54 (13) | O1A—C35A—N3A | 124.1 (7) |
C11—C12—H12A | 109.5 | O1A—C35A—H35A | 118.0 |
C11—C12—H12B | 109.5 | N3A—C35A—H35A | 118.0 |
C11—C12—H12C | 109.5 | N3A—C36A—H36D | 109.5 |
H12A—C12—H12B | 109.5 | N3A—C36A—H36F | 109.5 |
H12A—C12—H12C | 109.5 | N3A—C36A—H36E | 109.5 |
H12B—C12—H12C | 109.5 | H36D—C36A—H36F | 109.5 |
C14—C13—C10 | 121.90 (15) | H36D—C36A—H36E | 109.5 |
C17—C13—C10 | 121.58 (16) | H36F—C36A—H36E | 109.5 |
C17—C13—C14 | 116.46 (16) | N3A—C37A—H37D | 109.5 |
C13—C14—H14 | 120.0 | N3A—C37A—H37E | 109.5 |
C15—C14—C13 | 119.91 (17) | N3A—C37A—H37F | 109.5 |
C15—C14—H14 | 120.0 | H37D—C37A—H37E | 109.5 |
N1—C15—C14 | 122.95 (18) | H37D—C37A—H37F | 109.5 |
N1—C15—H15 | 118.5 | H37E—C37A—H37F | 109.5 |
C14—C15—H15 | 118.5 | C35—N3—C36 | 122.1 (6) |
N1—C16—H16 | 118.3 | C35—N3—C37 | 119.1 (7) |
N1—C16—C17 | 123.48 (18) | C36—N3—C37 | 118.2 (7) |
C17—C16—H16 | 118.3 | O1—C35—N3 | 130.7 (11) |
C13—C17—H17 | 120.0 | O1—C35—H35 | 114.7 |
C16—C17—C13 | 120.00 (19) | N3—C35—H35 | 114.7 |
C16—C17—H17 | 120.0 | N3—C36—H36A | 109.5 |
C1—C18—C19 | 123.48 (15) | N3—C36—H36B | 109.5 |
C1—C18—C25 | 121.07 (14) | N3—C36—H36C | 109.5 |
C25—C18—C19 | 115.45 (14) | H36A—C36—H36B | 109.5 |
C20—C19—C18 | 119.82 (15) | H36A—C36—H36C | 109.5 |
C24—C19—C18 | 122.00 (15) | H36B—C36—H36C | 109.5 |
C24—C19—C20 | 118.12 (15) | N3—C37—H37A | 109.5 |
C19—C20—H20 | 119.5 | N3—C37—H37B | 109.5 |
C21—C20—C19 | 120.96 (16) | N3—C37—H37C | 109.5 |
C21—C20—H20 | 119.5 | H37A—C37—H37B | 109.5 |
C20—C21—H21 | 119.9 | H37A—C37—H37C | 109.5 |
C20—C21—C22 | 120.25 (17) | H37B—C37—H37C | 109.5 |
Cu1—N1—C15—C14 | −179.18 (15) | C13—C14—C15—N1 | 0.5 (3) |
Cu1—N1—C16—C17 | 177.96 (19) | C14—C13—C17—C16 | −1.5 (3) |
Cu1iv—N2—C32—C31 | 173.36 (19) | C15—N1—C16—C17 | −1.0 (3) |
Cu1iv—N2—C33—C34 | −173.62 (15) | C16—N1—C15—C14 | −0.2 (3) |
S1—C10—C13—C14 | 174.71 (14) | C17—C13—C14—C15 | 0.4 (3) |
S1—C10—C13—C17 | −2.5 (2) | C18—C1—C2—C3 | 134.49 (18) |
S2—C27—C30—C31 | −167.11 (17) | C18—C1—C2—C7 | −52.0 (3) |
S2—C27—C30—C34 | 15.6 (3) | C18—C1—C8—C9 | −47.8 (2) |
N1—C16—C17—C13 | 1.9 (4) | C18—C1—C8—C11 | 133.02 (18) |
N2—C33—C34—C30 | 1.6 (3) | C18—C19—C20—C21 | 177.32 (18) |
C1—C2—C3—C4 | 174.81 (17) | C18—C19—C24—C23 | −177.63 (17) |
C1—C2—C7—C6 | −173.22 (18) | C18—C25—C26—C27 | −177.76 (15) |
C1—C8—C9—C10 | −179.77 (15) | C18—C25—C28—S2 | 178.07 (13) |
C1—C8—C11—S1 | −179.32 (12) | C18—C25—C28—C29 | −1.7 (3) |
C1—C8—C11—C12 | −0.2 (3) | C19—C18—C25—C26 | 128.71 (17) |
C1—C18—C19—C20 | 140.24 (18) | C19—C18—C25—C28 | −49.3 (2) |
C1—C18—C19—C24 | −42.8 (3) | C19—C20—C21—C22 | −0.1 (3) |
C1—C18—C25—C26 | −50.3 (2) | C20—C19—C24—C23 | −0.6 (3) |
C1—C18—C25—C28 | 131.62 (18) | C20—C21—C22—C23 | 0.4 (3) |
C2—C1—C8—C9 | 132.70 (17) | C21—C22—C23—C24 | −0.7 (3) |
C2—C1—C8—C11 | −46.5 (2) | C22—C23—C24—C19 | 0.9 (3) |
C2—C1—C18—C19 | −7.7 (3) | C24—C19—C20—C21 | 0.3 (3) |
C2—C1—C18—C25 | 171.21 (16) | C25—C18—C19—C20 | −38.8 (2) |
C2—C3—C4—C5 | −1.3 (3) | C25—C18—C19—C24 | 138.17 (17) |
C3—C2—C7—C6 | 0.4 (3) | C25—C26—C27—S2 | −0.57 (19) |
C3—C4—C5—C6 | 0.0 (3) | C25—C26—C27—C30 | 173.77 (17) |
C4—C5—C6—C7 | 1.5 (4) | C26—C25—C28—S2 | −0.19 (19) |
C5—C6—C7—C2 | −1.6 (3) | C26—C25—C28—C29 | 180.00 (17) |
C7—C2—C3—C4 | 1.1 (3) | C26—C27—C30—C31 | 19.1 (3) |
C8—C1—C2—C3 | −46.0 (2) | C26—C27—C30—C34 | −158.16 (19) |
C8—C1—C2—C7 | 127.50 (17) | C27—S2—C28—C25 | −0.11 (14) |
C8—C1—C18—C19 | 172.79 (15) | C27—S2—C28—C29 | 179.72 (15) |
C8—C1—C18—C25 | −8.2 (2) | C27—C30—C31—C32 | −172.4 (2) |
C8—C9—C10—S1 | −0.63 (18) | C27—C30—C34—C33 | 171.99 (18) |
C8—C9—C10—C13 | 176.47 (16) | C28—S2—C27—C26 | 0.39 (14) |
C9—C8—C11—S1 | 1.40 (18) | C28—S2—C27—C30 | −174.38 (15) |
C9—C8—C11—C12 | −179.51 (17) | C28—C25—C26—C27 | 0.5 (2) |
C9—C10—C13—C14 | −2.1 (3) | C30—C31—C32—N2 | −0.8 (4) |
C9—C10—C13—C17 | −179.27 (19) | C31—C30—C34—C33 | −5.4 (3) |
C10—S1—C11—C8 | −1.50 (13) | C32—N2—C33—C34 | 2.7 (3) |
C10—S1—C11—C12 | 179.30 (14) | C33—N2—C32—C31 | −3.1 (3) |
C10—C13—C14—C15 | −176.92 (17) | C34—C30—C31—C32 | 5.0 (3) |
C10—C13—C17—C16 | 175.8 (2) | C36A—N3A—C35A—O1A | 4.9 (12) |
C11—S1—C10—C9 | 1.22 (13) | C37A—N3A—C35A—O1A | −175.7 (11) |
C11—S1—C10—C13 | −176.13 (14) | C36—N3—C35—O1 | −170.9 (11) |
C11—C8—C9—C10 | −0.5 (2) | C37—N3—C35—O1 | −0.2 (14) |
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) x, y+1, z; (iii) −x+2, −y+1, −z+2; (iv) x, y−1, z. |
C42H31N3O7S2Zn·H2O | Z = 2 |
Mr = 837.20 | F(000) = 864 |
Triclinic, P1 | Dx = 1.464 Mg m−3 |
a = 10.1753 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.9520 (13) Å | Cell parameters from 8017 reflections |
c = 18.411 (2) Å | θ = 2.2–28.2° |
α = 89.839 (4)° | µ = 0.82 mm−1 |
β = 82.711 (4)° | T = 90 K |
γ = 69.145 (4)° | Prism, colourless |
V = 1899.8 (4) Å3 | 0.14 × 0.1 × 0.02 mm |
Bruker APEX-II CCD diffractometer | Rint = 0.053 |
φ and ω scans | θmax = 28.4°, θmin = 2.0° |
11887 measured reflections | h = −13→13 |
11887 independent reflections | k = −14→14 |
10577 reflections with I > 2σ(I) | l = 0→24 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0452P)2 + 2.0243P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
11887 reflections | Δρmax = 0.54 e Å−3 |
514 parameters | Δρmin = −0.68 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.88011 (4) | 0.29071 (4) | 0.47898 (2) | 0.00991 (8) | |
S1 | 0.62939 (8) | 0.76989 (8) | 0.19036 (4) | 0.01473 (17) | |
S2 | 1.26619 (8) | 0.76674 (8) | 0.18894 (5) | 0.01550 (17) | |
O1 | 0.8175 (2) | 0.4481 (2) | 0.55720 (12) | 0.0186 (5) | |
H1A | 0.825262 | 0.517148 | 0.536046 | 0.028* | |
H1B | 0.727035 | 0.470706 | 0.572668 | 0.028* | |
O3 | 0.7386 (2) | 0.2192 (2) | 0.53327 (12) | 0.0140 (5) | |
O4 | 0.6074 (2) | 0.3086 (2) | 0.44549 (13) | 0.0240 (6) | |
O5 | 0.1127 (2) | 0.3347 (2) | 0.47296 (13) | 0.0165 (5) | |
O6 | 0.0497 (2) | 0.1835 (2) | 0.53182 (12) | 0.0139 (4) | |
O7 | 0.3801 (3) | −0.0731 (3) | 0.70633 (16) | 0.0391 (8) | |
O8 | 0.6041 (3) | −0.1213 (3) | 0.66891 (16) | 0.0349 (7) | |
N1 | 0.8497 (3) | 0.4317 (3) | 0.39545 (14) | 0.0123 (5) | |
N2 | 0.9426 (3) | 1.1433 (3) | 0.39012 (14) | 0.0118 (5) | |
N3 | 0.4786 (3) | −0.0551 (3) | 0.66728 (17) | 0.0226 (7) | |
C1 | 0.9263 (3) | 0.7471 (3) | 0.01916 (17) | 0.0111 (6) | |
C2 | 0.8640 (3) | 0.7441 (3) | −0.04950 (17) | 0.0125 (6) | |
C3 | 0.8051 (3) | 0.6503 (3) | −0.06118 (18) | 0.0145 (7) | |
H3 | 0.809798 | 0.585401 | −0.026251 | 0.017* | |
C4 | 0.7393 (4) | 0.6495 (4) | −0.12322 (19) | 0.0201 (7) | |
H4 | 0.701737 | 0.583355 | −0.130927 | 0.024* | |
C5 | 0.7292 (3) | 0.7466 (4) | −0.17385 (19) | 0.0194 (7) | |
H5 | 0.682970 | 0.747881 | −0.215715 | 0.023* | |
C6 | 0.7869 (4) | 0.8413 (3) | −0.16273 (18) | 0.0183 (7) | |
H6 | 0.780323 | 0.907474 | −0.197071 | 0.022* | |
C7 | 0.8544 (3) | 0.8395 (3) | −0.10136 (18) | 0.0147 (7) | |
H7 | 0.894668 | 0.904039 | −0.094562 | 0.018* | |
C8 | 0.8389 (3) | 0.7383 (3) | 0.08847 (17) | 0.0115 (6) | |
C9 | 0.8946 (3) | 0.6566 (3) | 0.14680 (17) | 0.0115 (6) | |
H9 | 0.991924 | 0.603165 | 0.144812 | 0.014* | |
C10 | 0.7951 (3) | 0.6627 (3) | 0.20552 (17) | 0.0112 (6) | |
C11 | 0.6937 (3) | 0.8050 (3) | 0.10421 (17) | 0.0121 (6) | |
C12 | 0.5912 (3) | 0.8971 (3) | 0.05951 (19) | 0.0172 (7) | |
H12A | 0.556 (2) | 0.8441 (11) | 0.0250 (11) | 0.026* | |
H12B | 0.6414 (12) | 0.9511 (19) | 0.0284 (11) | 0.026* | |
H12C | 0.505 (2) | 0.9599 (19) | 0.0942 (7) | 0.026* | |
C13 | 0.8132 (3) | 0.5883 (3) | 0.27251 (17) | 0.0121 (6) | |
C14 | 0.9474 (3) | 0.5059 (4) | 0.28575 (19) | 0.0198 (7) | |
H14 | 1.029289 | 0.501913 | 0.253215 | 0.024* | |
C15 | 0.9607 (3) | 0.4303 (3) | 0.34627 (18) | 0.0183 (7) | |
H15 | 1.053028 | 0.374113 | 0.353822 | 0.022* | |
C16 | 0.7213 (3) | 0.5137 (3) | 0.38345 (17) | 0.0125 (6) | |
H16 | 0.641583 | 0.518430 | 0.417865 | 0.015* | |
C17 | 0.6988 (3) | 0.5917 (3) | 0.32376 (17) | 0.0129 (6) | |
H17 | 0.605373 | 0.647473 | 0.317706 | 0.016* | |
C18 | 1.0569 (3) | 0.7563 (3) | 0.01916 (17) | 0.0102 (6) | |
C19 | 1.1577 (3) | 0.7427 (3) | −0.04989 (17) | 0.0113 (6) | |
C20 | 1.2256 (3) | 0.8335 (3) | −0.06275 (18) | 0.0147 (7) | |
H20 | 1.202362 | 0.906538 | −0.029467 | 0.018* | |
C21 | 1.3271 (3) | 0.8173 (3) | −0.12409 (18) | 0.0161 (7) | |
H21 | 1.371251 | 0.880152 | −0.132794 | 0.019* | |
C22 | 1.3639 (3) | 0.7099 (3) | −0.17238 (18) | 0.0176 (7) | |
H22 | 1.433755 | 0.698495 | −0.213827 | 0.021* | |
C23 | 1.2981 (3) | 0.6192 (3) | −0.15973 (18) | 0.0153 (7) | |
H23 | 1.323387 | 0.545141 | −0.192522 | 0.018* | |
C24 | 1.1949 (3) | 0.6359 (3) | −0.09916 (17) | 0.0138 (6) | |
H24 | 1.149590 | 0.573759 | −0.091453 | 0.017* | |
C25 | 1.1101 (3) | 0.7786 (3) | 0.08756 (17) | 0.0105 (6) | |
C26 | 1.0247 (3) | 0.8704 (3) | 0.14483 (17) | 0.0111 (6) | |
H26 | 0.928545 | 0.923247 | 0.142403 | 0.013* | |
C27 | 1.0924 (3) | 0.8762 (3) | 0.20358 (17) | 0.0115 (6) | |
C28 | 1.2480 (3) | 0.7143 (3) | 0.10393 (17) | 0.0126 (6) | |
C29 | 1.3754 (3) | 0.6182 (3) | 0.05882 (19) | 0.0172 (7) | |
H29A | 1.4203 (17) | 0.6668 (10) | 0.0223 (11) | 0.026* | |
H29B | 1.3456 (7) | 0.5541 (19) | 0.0313 (11) | 0.026* | |
H29C | 1.4471 (18) | 0.5685 (18) | 0.0922 (7) | 0.026* | |
C30 | 1.0393 (3) | 0.9636 (3) | 0.26917 (17) | 0.0107 (6) | |
C31 | 0.9249 (3) | 1.0814 (3) | 0.26775 (17) | 0.0143 (6) | |
H31 | 0.878171 | 1.102124 | 0.225389 | 0.017* | |
C32 | 0.8806 (3) | 1.1670 (3) | 0.32801 (18) | 0.0147 (6) | |
H32 | 0.802809 | 1.246457 | 0.326022 | 0.018* | |
C33 | 1.0495 (3) | 1.0281 (3) | 0.39221 (17) | 0.0127 (6) | |
H33 | 1.092728 | 1.008613 | 0.435742 | 0.015* | |
C34 | 1.0996 (3) | 0.9367 (3) | 0.33418 (17) | 0.0134 (6) | |
H34 | 1.174545 | 0.856060 | 0.338436 | 0.016* | |
C35 | 0.5203 (3) | 0.1863 (3) | 0.53285 (16) | 0.0108 (6) | |
C36 | 0.3855 (3) | 0.2320 (3) | 0.51095 (16) | 0.0108 (6) | |
H36 | 0.365394 | 0.295922 | 0.474891 | 0.013* | |
C37 | 0.2799 (3) | 0.1866 (3) | 0.54041 (16) | 0.0101 (6) | |
C38 | 0.3077 (3) | 0.0933 (3) | 0.59379 (17) | 0.0135 (6) | |
H38 | 0.236750 | 0.061791 | 0.615493 | 0.016* | |
C39 | 0.4438 (3) | 0.0483 (3) | 0.61387 (17) | 0.0142 (6) | |
C40 | 0.5501 (3) | 0.0924 (3) | 0.58536 (17) | 0.0134 (6) | |
H40 | 0.641121 | 0.059413 | 0.601182 | 0.016* | |
C41 | 0.6292 (3) | 0.2430 (3) | 0.50055 (17) | 0.0136 (7) | |
C42 | 0.1374 (3) | 0.2394 (3) | 0.51373 (16) | 0.0113 (6) | |
O2 | 0.4201 (3) | 0.4054 (3) | 0.34587 (16) | 0.0319 (6) | |
H2A | 0.483868 | 0.371822 | 0.374834 | 0.048* | |
H2B | 0.401572 | 0.339194 | 0.330221 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.00675 (14) | 0.01289 (16) | 0.00995 (15) | −0.00338 (12) | −0.00105 (14) | 0.00258 (16) |
S1 | 0.0104 (3) | 0.0189 (4) | 0.0130 (4) | −0.0034 (3) | −0.0003 (3) | 0.0051 (3) |
S2 | 0.0106 (4) | 0.0191 (4) | 0.0148 (4) | −0.0023 (3) | −0.0036 (3) | −0.0007 (3) |
O1 | 0.0195 (11) | 0.0165 (12) | 0.0200 (12) | −0.0080 (9) | 0.0017 (9) | 0.0009 (10) |
O3 | 0.0091 (10) | 0.0198 (12) | 0.0146 (12) | −0.0072 (9) | −0.0011 (8) | 0.0022 (9) |
O4 | 0.0153 (11) | 0.0339 (14) | 0.0260 (14) | −0.0120 (10) | −0.0049 (10) | 0.0192 (11) |
O5 | 0.0112 (10) | 0.0215 (12) | 0.0177 (12) | −0.0058 (9) | −0.0056 (9) | 0.0075 (10) |
O6 | 0.0085 (10) | 0.0150 (11) | 0.0196 (12) | −0.0055 (8) | −0.0031 (8) | −0.0015 (9) |
O7 | 0.0275 (14) | 0.0550 (19) | 0.0473 (18) | −0.0277 (14) | −0.0132 (13) | 0.0366 (15) |
O8 | 0.0222 (13) | 0.0394 (17) | 0.0436 (18) | −0.0085 (12) | −0.0147 (12) | 0.0263 (14) |
N1 | 0.0109 (12) | 0.0148 (14) | 0.0125 (14) | −0.0062 (11) | −0.0015 (10) | 0.0011 (11) |
N2 | 0.0090 (12) | 0.0133 (13) | 0.0129 (13) | −0.0042 (10) | −0.0004 (10) | 0.0010 (10) |
N3 | 0.0202 (14) | 0.0264 (16) | 0.0277 (17) | −0.0139 (13) | −0.0111 (12) | 0.0155 (13) |
C1 | 0.0119 (14) | 0.0119 (15) | 0.0095 (15) | −0.0039 (12) | −0.0027 (11) | 0.0036 (12) |
C2 | 0.0100 (14) | 0.0169 (16) | 0.0110 (16) | −0.0050 (12) | −0.0025 (12) | 0.0030 (13) |
C3 | 0.0179 (16) | 0.0160 (16) | 0.0138 (16) | −0.0101 (14) | −0.0050 (12) | 0.0058 (13) |
C4 | 0.0234 (17) | 0.0250 (19) | 0.0175 (18) | −0.0141 (15) | −0.0068 (14) | 0.0028 (15) |
C5 | 0.0168 (16) | 0.031 (2) | 0.0131 (17) | −0.0102 (15) | −0.0061 (13) | 0.0025 (14) |
C6 | 0.0156 (15) | 0.0247 (19) | 0.0159 (16) | −0.0082 (14) | −0.0038 (13) | 0.0107 (14) |
C7 | 0.0143 (15) | 0.0189 (17) | 0.0138 (16) | −0.0092 (13) | −0.0021 (12) | 0.0048 (13) |
C8 | 0.0127 (14) | 0.0126 (16) | 0.0116 (16) | −0.0069 (12) | −0.0036 (12) | 0.0031 (12) |
C9 | 0.0098 (14) | 0.0123 (15) | 0.0128 (16) | −0.0038 (12) | −0.0043 (12) | 0.0040 (12) |
C10 | 0.0097 (13) | 0.0122 (15) | 0.0117 (16) | −0.0040 (12) | −0.0015 (11) | −0.0005 (12) |
C11 | 0.0105 (14) | 0.0152 (16) | 0.0115 (16) | −0.0057 (12) | −0.0018 (12) | 0.0027 (13) |
C12 | 0.0140 (15) | 0.0195 (18) | 0.0162 (17) | −0.0027 (13) | −0.0048 (13) | 0.0034 (14) |
C13 | 0.0157 (15) | 0.0121 (15) | 0.0121 (16) | −0.0085 (12) | −0.0042 (12) | 0.0034 (12) |
C14 | 0.0106 (15) | 0.032 (2) | 0.0186 (17) | −0.0094 (14) | −0.0017 (12) | 0.0114 (15) |
C15 | 0.0101 (14) | 0.0267 (19) | 0.0194 (17) | −0.0069 (13) | −0.0058 (12) | 0.0085 (14) |
C16 | 0.0137 (14) | 0.0093 (14) | 0.0118 (15) | −0.0020 (12) | 0.0017 (11) | −0.0018 (12) |
C17 | 0.0118 (14) | 0.0110 (15) | 0.0126 (15) | −0.0012 (12) | 0.0019 (11) | −0.0008 (12) |
C18 | 0.0112 (14) | 0.0083 (14) | 0.0113 (15) | −0.0038 (12) | −0.0010 (11) | 0.0002 (12) |
C19 | 0.0084 (13) | 0.0131 (16) | 0.0123 (16) | −0.0032 (12) | −0.0033 (11) | 0.0043 (12) |
C20 | 0.0153 (15) | 0.0155 (16) | 0.0138 (16) | −0.0057 (13) | −0.0031 (12) | 0.0005 (14) |
C21 | 0.0146 (15) | 0.0193 (17) | 0.0167 (17) | −0.0092 (13) | −0.0008 (12) | 0.0039 (13) |
C22 | 0.0127 (15) | 0.0257 (19) | 0.0124 (16) | −0.0051 (14) | 0.0006 (12) | 0.0021 (14) |
C23 | 0.0135 (15) | 0.0175 (17) | 0.0127 (16) | −0.0034 (13) | −0.0005 (12) | −0.0014 (13) |
C24 | 0.0130 (15) | 0.0143 (16) | 0.0145 (17) | −0.0051 (13) | −0.0018 (12) | 0.0013 (13) |
C25 | 0.0109 (14) | 0.0108 (15) | 0.0106 (15) | −0.0050 (12) | −0.0013 (11) | 0.0018 (12) |
C26 | 0.0113 (14) | 0.0120 (15) | 0.0118 (16) | −0.0062 (12) | −0.0015 (11) | 0.0034 (12) |
C27 | 0.0090 (13) | 0.0120 (15) | 0.0133 (16) | −0.0044 (12) | 0.0015 (11) | 0.0008 (12) |
C28 | 0.0088 (14) | 0.0171 (17) | 0.0112 (16) | −0.0048 (12) | 0.0018 (11) | −0.0018 (13) |
C29 | 0.0124 (15) | 0.0172 (17) | 0.0185 (18) | −0.0018 (13) | 0.0003 (13) | −0.0003 (14) |
C30 | 0.0082 (13) | 0.0144 (16) | 0.0110 (15) | −0.0063 (12) | 0.0000 (11) | 0.0012 (12) |
C31 | 0.0119 (14) | 0.0190 (17) | 0.0131 (16) | −0.0054 (12) | −0.0052 (12) | 0.0023 (13) |
C32 | 0.0101 (14) | 0.0169 (16) | 0.0168 (16) | −0.0039 (12) | −0.0034 (12) | 0.0015 (13) |
C33 | 0.0123 (14) | 0.0157 (16) | 0.0119 (15) | −0.0067 (12) | −0.0034 (11) | 0.0029 (12) |
C34 | 0.0123 (14) | 0.0122 (15) | 0.0153 (16) | −0.0034 (12) | −0.0037 (11) | 0.0014 (12) |
C35 | 0.0092 (13) | 0.0111 (14) | 0.0109 (15) | −0.0029 (11) | 0.0006 (11) | −0.0017 (12) |
C36 | 0.0104 (13) | 0.0125 (14) | 0.0095 (15) | −0.0042 (11) | −0.0013 (11) | 0.0017 (11) |
C37 | 0.0068 (13) | 0.0111 (14) | 0.0121 (14) | −0.0026 (11) | −0.0017 (10) | −0.0002 (11) |
C38 | 0.0110 (14) | 0.0152 (15) | 0.0161 (16) | −0.0067 (12) | −0.0023 (11) | 0.0023 (12) |
C39 | 0.0135 (14) | 0.0138 (15) | 0.0162 (16) | −0.0045 (12) | −0.0061 (12) | 0.0081 (13) |
C40 | 0.0092 (13) | 0.0169 (16) | 0.0142 (15) | −0.0041 (12) | −0.0037 (11) | 0.0014 (12) |
C41 | 0.0075 (12) | 0.0161 (16) | 0.0166 (16) | −0.0036 (12) | −0.0006 (11) | −0.0001 (12) |
C42 | 0.0091 (13) | 0.0133 (15) | 0.0104 (14) | −0.0025 (11) | −0.0025 (11) | −0.0024 (11) |
O2 | 0.0245 (14) | 0.0375 (16) | 0.0246 (15) | −0.0009 (12) | −0.0015 (11) | 0.0057 (13) |
Zn1—O1 | 2.110 (2) | C14—C15 | 1.378 (4) |
Zn1—O3 | 2.030 (2) | C15—H15 | 0.9500 |
Zn1—O6i | 2.069 (2) | C16—H16 | 0.9500 |
Zn1—N1 | 2.147 (3) | C16—C17 | 1.382 (4) |
Zn1—N2ii | 2.170 (3) | C17—H17 | 0.9500 |
S1—C10 | 1.734 (3) | C18—C19 | 1.500 (4) |
S1—C11 | 1.733 (3) | C18—C25 | 1.485 (4) |
S2—C27 | 1.734 (3) | C19—C20 | 1.403 (4) |
S2—C28 | 1.723 (3) | C19—C24 | 1.392 (4) |
O1—H1A | 0.8733 | C20—H20 | 0.9500 |
O1—H1B | 0.8730 | C20—C21 | 1.396 (4) |
O3—C41 | 1.278 (4) | C21—H21 | 0.9500 |
O4—C41 | 1.238 (4) | C21—C22 | 1.386 (5) |
O5—C42 | 1.254 (4) | C22—H22 | 0.9500 |
O6—C42 | 1.264 (4) | C22—C23 | 1.387 (5) |
O7—N3 | 1.232 (4) | C23—H23 | 0.9500 |
O8—N3 | 1.228 (4) | C23—C24 | 1.395 (4) |
N1—C15 | 1.351 (4) | C24—H24 | 0.9500 |
N1—C16 | 1.341 (4) | C25—C26 | 1.424 (4) |
N2—C32 | 1.356 (4) | C25—C28 | 1.399 (4) |
N2—C33 | 1.346 (4) | C26—H26 | 0.9500 |
N3—C39 | 1.474 (4) | C26—C27 | 1.367 (4) |
C1—C2 | 1.490 (4) | C27—C30 | 1.463 (4) |
C1—C8 | 1.484 (4) | C28—C29 | 1.496 (4) |
C1—C18 | 1.368 (4) | C29—H29A | 1.02 (2) |
C2—C3 | 1.390 (4) | C29—H29B | 1.02 (2) |
C2—C7 | 1.400 (4) | C29—H29C | 1.02 (2) |
C3—H3 | 0.9500 | C30—C31 | 1.399 (4) |
C3—C4 | 1.397 (4) | C30—C34 | 1.397 (4) |
C4—H4 | 0.9500 | C31—H31 | 0.9500 |
C4—C5 | 1.397 (5) | C31—C32 | 1.375 (4) |
C5—H5 | 0.9500 | C32—H32 | 0.9500 |
C5—C6 | 1.389 (5) | C33—H33 | 0.9500 |
C6—H6 | 0.9500 | C33—C34 | 1.381 (4) |
C6—C7 | 1.391 (4) | C34—H34 | 0.9500 |
C7—H7 | 0.9500 | C35—C36 | 1.395 (4) |
C8—C9 | 1.436 (4) | C35—C40 | 1.390 (4) |
C8—C11 | 1.387 (4) | C35—C41 | 1.512 (4) |
C9—H9 | 0.9500 | C36—H36 | 0.9500 |
C9—C10 | 1.369 (4) | C36—C37 | 1.388 (4) |
C10—C13 | 1.471 (4) | C37—C38 | 1.396 (4) |
C11—C12 | 1.499 (4) | C37—C42 | 1.503 (4) |
C12—H12A | 1.04 (2) | C38—H38 | 0.9500 |
C12—H12B | 1.04 (2) | C38—C39 | 1.393 (4) |
C12—H12C | 1.04 (2) | C39—C40 | 1.380 (4) |
C13—C14 | 1.394 (4) | C40—H40 | 0.9500 |
C13—C17 | 1.392 (4) | O2—H2A | 0.8701 |
C14—H14 | 0.9500 | O2—H2B | 0.8696 |
O1—Zn1—N1 | 87.84 (9) | C1—C18—C19 | 122.4 (3) |
O1—Zn1—N2ii | 174.22 (9) | C1—C18—C25 | 122.5 (3) |
O3—Zn1—O1 | 90.57 (9) | C25—C18—C19 | 115.2 (2) |
O3—Zn1—O6i | 95.95 (8) | C20—C19—C18 | 119.7 (3) |
O3—Zn1—N1 | 129.22 (9) | C24—C19—C18 | 121.6 (3) |
O3—Zn1—N2ii | 93.34 (9) | C24—C19—C20 | 118.5 (3) |
O6i—Zn1—O1 | 92.11 (9) | C19—C20—H20 | 119.8 |
O6i—Zn1—N1 | 134.83 (9) | C21—C20—C19 | 120.5 (3) |
O6i—Zn1—N2ii | 91.71 (9) | C21—C20—H20 | 119.8 |
N1—Zn1—N2ii | 86.39 (9) | C20—C21—H21 | 119.8 |
C11—S1—C10 | 92.75 (14) | C22—C21—C20 | 120.3 (3) |
C28—S2—C27 | 93.10 (15) | C22—C21—H21 | 119.8 |
Zn1—O1—H1A | 109.6 | C21—C22—H22 | 120.2 |
Zn1—O1—H1B | 109.4 | C21—C22—C23 | 119.5 (3) |
H1A—O1—H1B | 104.3 | C23—C22—H22 | 120.2 |
C41—O3—Zn1 | 111.36 (19) | C22—C23—H23 | 119.8 |
C42—O6—Zn1iii | 101.92 (18) | C22—C23—C24 | 120.4 (3) |
C15—N1—Zn1 | 120.1 (2) | C24—C23—H23 | 119.8 |
C16—N1—Zn1 | 123.1 (2) | C19—C24—C23 | 120.7 (3) |
C16—N1—C15 | 116.4 (3) | C19—C24—H24 | 119.6 |
C32—N2—Zn1iv | 121.0 (2) | C23—C24—H24 | 119.6 |
C33—N2—Zn1iv | 121.8 (2) | C26—C25—C18 | 123.2 (3) |
C33—N2—C32 | 117.1 (3) | C28—C25—C18 | 125.1 (3) |
O7—N3—C39 | 118.2 (3) | C28—C25—C26 | 111.7 (3) |
O8—N3—O7 | 123.5 (3) | C25—C26—H26 | 122.7 |
O8—N3—C39 | 118.2 (3) | C27—C26—C25 | 114.6 (3) |
C8—C1—C2 | 116.1 (3) | C27—C26—H26 | 122.7 |
C18—C1—C2 | 122.6 (3) | C26—C27—S2 | 110.0 (2) |
C18—C1—C8 | 121.3 (3) | C26—C27—C30 | 128.8 (3) |
C3—C2—C1 | 120.2 (3) | C30—C27—S2 | 121.1 (2) |
C3—C2—C7 | 118.2 (3) | C25—C28—S2 | 110.7 (2) |
C7—C2—C1 | 121.4 (3) | C25—C28—C29 | 130.6 (3) |
C2—C3—H3 | 119.3 | C29—C28—S2 | 118.7 (2) |
C2—C3—C4 | 121.4 (3) | C28—C29—H29A | 109.5 |
C4—C3—H3 | 119.3 | C28—C29—H29B | 109.5 |
C3—C4—H4 | 120.2 | C28—C29—H29C | 109.5 |
C3—C4—C5 | 119.5 (3) | H29A—C29—H29B | 109.5 |
C5—C4—H4 | 120.2 | H29A—C29—H29C | 109.5 |
C4—C5—H5 | 120.1 | H29B—C29—H29C | 109.5 |
C6—C5—C4 | 119.7 (3) | C31—C30—C27 | 119.7 (3) |
C6—C5—H5 | 120.1 | C34—C30—C27 | 122.9 (3) |
C5—C6—H6 | 120.0 | C34—C30—C31 | 117.3 (3) |
C5—C6—C7 | 120.1 (3) | C30—C31—H31 | 120.2 |
C7—C6—H6 | 120.0 | C32—C31—C30 | 119.6 (3) |
C2—C7—H7 | 119.5 | C32—C31—H31 | 120.2 |
C6—C7—C2 | 121.0 (3) | N2—C32—C31 | 123.1 (3) |
C6—C7—H7 | 119.5 | N2—C32—H32 | 118.4 |
C9—C8—C1 | 123.7 (3) | C31—C32—H32 | 118.4 |
C11—C8—C1 | 124.4 (3) | N2—C33—H33 | 118.4 |
C11—C8—C9 | 111.9 (3) | N2—C33—C34 | 123.2 (3) |
C8—C9—H9 | 123.0 | C34—C33—H33 | 118.4 |
C10—C9—C8 | 114.0 (3) | C30—C34—H34 | 120.2 |
C10—C9—H9 | 123.0 | C33—C34—C30 | 119.5 (3) |
C9—C10—S1 | 110.5 (2) | C33—C34—H34 | 120.2 |
C9—C10—C13 | 128.5 (3) | C36—C35—C41 | 119.2 (3) |
C13—C10—S1 | 120.9 (2) | C40—C35—C36 | 119.2 (3) |
C8—C11—S1 | 110.9 (2) | C40—C35—C41 | 121.5 (3) |
C8—C11—C12 | 130.6 (3) | C35—C36—H36 | 119.1 |
C12—C11—S1 | 118.5 (2) | C37—C36—C35 | 121.8 (3) |
C11—C12—H12A | 109.5 | C37—C36—H36 | 119.1 |
C11—C12—H12B | 109.5 | C36—C37—C38 | 119.7 (3) |
C11—C12—H12C | 109.5 | C36—C37—C42 | 118.9 (3) |
H12A—C12—H12B | 109.5 | C38—C37—C42 | 121.4 (3) |
H12A—C12—H12C | 109.5 | C37—C38—H38 | 121.4 |
H12B—C12—H12C | 109.5 | C39—C38—C37 | 117.1 (3) |
C14—C13—C10 | 120.7 (3) | C39—C38—H38 | 121.4 |
C17—C13—C10 | 122.4 (3) | C38—C39—N3 | 118.5 (3) |
C17—C13—C14 | 116.8 (3) | C40—C39—N3 | 117.5 (3) |
C13—C14—H14 | 120.2 | C40—C39—C38 | 124.0 (3) |
C15—C14—C13 | 119.7 (3) | C35—C40—H40 | 120.9 |
C15—C14—H14 | 120.2 | C39—C40—C35 | 118.1 (3) |
N1—C15—C14 | 123.7 (3) | C39—C40—H40 | 120.9 |
N1—C15—H15 | 118.2 | O3—C41—C35 | 116.4 (3) |
C14—C15—H15 | 118.2 | O4—C41—O3 | 124.5 (3) |
N1—C16—H16 | 118.2 | O4—C41—C35 | 119.1 (3) |
N1—C16—C17 | 123.6 (3) | O5—C42—O6 | 123.1 (3) |
C17—C16—H16 | 118.2 | O5—C42—C37 | 118.4 (3) |
C13—C17—H17 | 120.1 | O6—C42—C37 | 118.5 (3) |
C16—C17—C13 | 119.9 (3) | H2A—O2—H2B | 104.5 |
C16—C17—H17 | 120.1 | ||
Zn1—O3—C41—O4 | −4.5 (4) | C16—N1—C15—C14 | −0.9 (5) |
Zn1—O3—C41—C35 | 175.9 (2) | C17—C13—C14—C15 | 1.8 (5) |
Zn1iii—O6—C42—O5 | −0.4 (3) | C18—C1—C2—C3 | 132.1 (3) |
Zn1iii—O6—C42—C37 | −178.5 (2) | C18—C1—C2—C7 | −52.1 (4) |
Zn1—N1—C15—C14 | 171.5 (3) | C18—C1—C8—C9 | −43.7 (4) |
Zn1—N1—C16—C17 | −170.6 (2) | C18—C1—C8—C11 | 137.7 (3) |
Zn1iv—N2—C32—C31 | 174.1 (2) | C18—C19—C20—C21 | 175.5 (3) |
Zn1iv—N2—C33—C34 | −174.5 (2) | C18—C19—C24—C23 | −174.3 (3) |
S1—C10—C13—C14 | −177.6 (3) | C18—C25—C26—C27 | 179.6 (3) |
S1—C10—C13—C17 | 5.2 (4) | C18—C25—C28—S2 | −179.4 (2) |
S2—C27—C30—C31 | 154.9 (2) | C18—C25—C28—C29 | 4.3 (5) |
S2—C27—C30—C34 | −23.7 (4) | C19—C18—C25—C26 | 137.7 (3) |
O7—N3—C39—C38 | −19.2 (5) | C19—C18—C25—C28 | −41.9 (4) |
O7—N3—C39—C40 | 162.4 (3) | C19—C20—C21—C22 | −1.2 (5) |
O8—N3—C39—C38 | 158.7 (3) | C20—C19—C24—C23 | 0.4 (4) |
O8—N3—C39—C40 | −19.7 (5) | C20—C21—C22—C23 | 0.6 (5) |
N1—C16—C17—C13 | −0.6 (5) | C21—C22—C23—C24 | 0.4 (5) |
N2—C33—C34—C30 | 0.9 (5) | C22—C23—C24—C19 | −0.9 (5) |
N3—C39—C40—C35 | 177.6 (3) | C24—C19—C20—C21 | 0.7 (4) |
C1—C2—C3—C4 | 176.6 (3) | C25—C18—C19—C20 | −47.6 (4) |
C1—C2—C7—C6 | −175.4 (3) | C25—C18—C19—C24 | 127.1 (3) |
C1—C8—C9—C10 | −179.6 (3) | C25—C26—C27—S2 | 0.1 (3) |
C1—C8—C11—S1 | −179.9 (3) | C25—C26—C27—C30 | 176.3 (3) |
C1—C8—C11—C12 | 0.4 (6) | C26—C25—C28—S2 | 1.0 (3) |
C1—C18—C19—C20 | 133.3 (3) | C26—C25—C28—C29 | −175.3 (3) |
C1—C18—C19—C24 | −52.1 (4) | C26—C27—C30—C31 | −20.9 (5) |
C1—C18—C25—C26 | −43.1 (4) | C26—C27—C30—C34 | 160.4 (3) |
C1—C18—C25—C28 | 137.3 (3) | C27—S2—C28—C25 | −0.8 (2) |
C2—C1—C8—C9 | 135.7 (3) | C27—S2—C28—C29 | 176.0 (3) |
C2—C1—C8—C11 | −42.8 (5) | C27—C30—C31—C32 | −176.1 (3) |
C2—C1—C18—C19 | −10.0 (4) | C27—C30—C34—C33 | 175.7 (3) |
C2—C1—C18—C25 | 170.9 (3) | C28—S2—C27—C26 | 0.4 (2) |
C2—C3—C4—C5 | −1.5 (5) | C28—S2—C27—C30 | −176.1 (3) |
C3—C2—C7—C6 | 0.5 (5) | C28—C25—C26—C27 | −0.7 (4) |
C3—C4—C5—C6 | 1.2 (5) | C30—C31—C32—N2 | 0.0 (5) |
C4—C5—C6—C7 | −0.1 (5) | C31—C30—C34—C33 | −3.0 (4) |
C5—C6—C7—C2 | −0.8 (5) | C32—N2—C33—C34 | 1.6 (4) |
C7—C2—C3—C4 | 0.7 (5) | C33—N2—C32—C31 | −2.1 (4) |
C8—C1—C2—C3 | −47.4 (4) | C34—C30—C31—C32 | 2.6 (4) |
C8—C1—C2—C7 | 128.4 (3) | C35—C36—C37—C38 | 0.4 (5) |
C8—C1—C18—C19 | 169.4 (3) | C35—C36—C37—C42 | −179.5 (3) |
C8—C1—C18—C25 | −9.6 (4) | C36—C35—C40—C39 | −0.1 (5) |
C8—C9—C10—S1 | −0.1 (4) | C36—C35—C41—O3 | 165.5 (3) |
C8—C9—C10—C13 | 176.8 (3) | C36—C35—C41—O4 | −14.2 (4) |
C9—C8—C11—S1 | 1.4 (4) | C36—C37—C38—C39 | −1.2 (4) |
C9—C8—C11—C12 | −178.3 (3) | C36—C37—C42—O5 | −9.2 (4) |
C9—C10—C13—C14 | 5.8 (5) | C36—C37—C42—O6 | 168.9 (3) |
C9—C10—C13—C17 | −171.3 (3) | C37—C38—C39—N3 | −176.9 (3) |
C10—S1—C11—C8 | −1.3 (3) | C37—C38—C39—C40 | 1.4 (5) |
C10—S1—C11—C12 | 178.5 (3) | C38—C37—C42—O5 | 171.0 (3) |
C10—C13—C14—C15 | −175.5 (3) | C38—C37—C42—O6 | −10.9 (4) |
C10—C13—C17—C16 | 176.1 (3) | C38—C39—C40—C35 | −0.7 (5) |
C11—S1—C10—C9 | 0.7 (3) | C40—C35—C36—C37 | 0.3 (5) |
C11—S1—C10—C13 | −176.4 (3) | C40—C35—C41—O3 | −12.7 (4) |
C11—C8—C9—C10 | −0.9 (4) | C40—C35—C41—O4 | 167.6 (3) |
C13—C14—C15—N1 | −0.8 (6) | C41—C35—C36—C37 | −177.9 (3) |
C14—C13—C17—C16 | −1.2 (5) | C41—C35—C40—C39 | 178.0 (3) |
C15—N1—C16—C17 | 1.6 (5) | C42—C37—C38—C39 | 178.7 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z; (iii) x−1, y, z; (iv) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O5v | 0.87 | 1.94 | 2.751 (3) | 154 |
O1—H1B···O2v | 0.87 | 2.08 | 2.787 (4) | 138 |
O2—H2A···O4 | 0.87 | 1.88 | 2.749 (3) | 174 |
Symmetry code: (v) −x+1, −y+1, −z+1. |
C82H60N4O5S4Zn | Z = 2 |
Mr = 1374.95 | F(000) = 1428 |
Triclinic, P1 | Dx = 1.375 Mg m−3 |
a = 14.2712 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.7916 (9) Å | Cell parameters from 9325 reflections |
c = 19.2839 (12) Å | θ = 2.3–27.9° |
α = 98.124 (2)° | µ = 0.56 mm−1 |
β = 104.400 (2)° | T = 90 K |
γ = 117.968 (2)° | Needle, colourless |
V = 3320.3 (4) Å3 | 0.14 × 0.02 × 0.01 mm |
Bruker APEX-II CCD diffractometer | 11914 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.047 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1237 before and 0.0537 after correction. The Ratio of minimum to maximum transmission is 0.9102. The λ/2 correction factor is Not present. | θmax = 28.3°, θmin = 1.6° |
Tmin = 0.679, Tmax = 0.746 | h = −19→18 |
41065 measured reflections | k = −17→19 |
16450 independent reflections | l = −25→19 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.036P)2 + 1.4334P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
16450 reflections | Δρmax = 0.46 e Å−3 |
873 parameters | Δρmin = −0.48 e Å−3 |
0 restraints |
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 | ||
Zn1 | 0.61425 (2) | −0.02027 (2) | 0.31880 (2) | 0.01156 (6) | |
S1 | 0.57310 (5) | −0.11665 (5) | −0.08197 (3) | 0.01755 (12) | |
S2 | 0.90876 (5) | 0.39168 (5) | 0.04897 (3) | 0.02368 (13) | |
S3 | 0.87073 (5) | 0.57237 (4) | 0.47846 (3) | 0.01569 (12) | |
S4 | 0.83507 (5) | 0.43429 (4) | 0.73718 (3) | 0.01831 (12) | |
O1 | 0.51238 (14) | −0.07504 (13) | 0.38157 (10) | 0.0236 (4) | |
O2 | 0.42029 (14) | −0.09369 (13) | 0.26554 (10) | 0.0242 (4) | |
O3 | 0.02100 (13) | −0.26509 (12) | 0.39696 (9) | 0.0203 (4) | |
O4 | −0.22448 (13) | 0.00233 (12) | 0.37492 (8) | 0.0178 (3) | |
O5 | −0.36888 (13) | −0.16196 (12) | 0.31151 (9) | 0.0190 (3) | |
N1 | 0.63085 (15) | −0.01824 (14) | 0.21446 (10) | 0.0130 (4) | |
N2 | 0.49595 (19) | 0.3369 (2) | −0.07438 (13) | 0.0369 (6) | |
N3 | 0.66189 (15) | 0.14022 (14) | 0.36232 (9) | 0.0129 (4) | |
N4 | 1.28917 (16) | 0.67255 (16) | 0.79088 (11) | 0.0231 (4) | |
C1 | 0.87471 (19) | 0.06732 (18) | −0.10097 (12) | 0.0164 (5) | |
C2 | 0.90214 (18) | 0.00047 (18) | −0.14789 (12) | 0.0164 (5) | |
C3 | 0.8999 (2) | −0.08940 (18) | −0.13187 (13) | 0.0214 (5) | |
H3 | 0.874826 | −0.112331 | −0.092835 | 0.026* | |
C4 | 0.9340 (2) | −0.14567 (18) | −0.17241 (14) | 0.0228 (5) | |
H4 | 0.933809 | −0.205860 | −0.160382 | 0.027* | |
C5 | 0.96838 (19) | −0.11398 (18) | −0.23032 (13) | 0.0212 (5) | |
H5 | 0.992726 | −0.151891 | −0.257613 | 0.025* | |
C6 | 0.96740 (19) | −0.02731 (18) | −0.24864 (13) | 0.0197 (5) | |
H6 | 0.989633 | −0.006411 | −0.289051 | 0.024* | |
C7 | 0.93394 (19) | 0.02869 (18) | −0.20792 (12) | 0.0177 (5) | |
H7 | 0.932567 | 0.087687 | −0.221086 | 0.021* | |
C8 | 0.77356 (19) | 0.00905 (18) | −0.07980 (12) | 0.0167 (5) | |
C9 | 0.77996 (19) | 0.02635 (18) | −0.00418 (12) | 0.0182 (5) | |
H9 | 0.848653 | 0.075857 | 0.036969 | 0.022* | |
C10 | 0.67845 (18) | −0.03455 (18) | 0.00439 (12) | 0.0160 (4) | |
C11 | 0.66566 (19) | −0.06820 (18) | −0.12880 (12) | 0.0166 (5) | |
C12 | 0.6227 (2) | −0.1085 (2) | −0.21267 (12) | 0.0239 (5) | |
H12A | 0.6519 (12) | −0.1525 (12) | −0.2278 (3) | 0.036* | |
H12B | 0.6483 (12) | −0.0481 (9) | −0.2326 (3) | 0.036* | |
H12C | 0.5403 (12) | −0.1511 (12) | −0.2320 (3) | 0.036* | |
C13 | 0.65810 (19) | −0.03298 (17) | 0.07500 (12) | 0.0155 (4) | |
C14 | 0.74548 (19) | −0.00790 (18) | 0.14043 (12) | 0.0191 (5) | |
H14 | 0.816261 | 0.004461 | 0.138513 | 0.023* | |
C15 | 0.72923 (19) | −0.00106 (18) | 0.20771 (12) | 0.0183 (5) | |
H15 | 0.790262 | 0.016639 | 0.251695 | 0.022* | |
C16 | 0.54625 (19) | −0.04410 (17) | 0.15155 (12) | 0.0162 (5) | |
H16 | 0.476005 | −0.057183 | 0.155057 | 0.019* | |
C17 | 0.55560 (19) | −0.05285 (17) | 0.08151 (12) | 0.0168 (5) | |
H17 | 0.492675 | −0.072241 | 0.038262 | 0.020* | |
C18 | 0.94243 (19) | 0.17575 (18) | −0.07561 (12) | 0.0172 (5) | |
C19 | 1.05509 (19) | 0.23495 (18) | −0.08403 (12) | 0.0177 (5) | |
C20 | 1.0830 (2) | 0.32250 (19) | −0.11214 (13) | 0.0232 (5) | |
H20 | 1.030999 | 0.345833 | −0.124515 | 0.028* | |
C21 | 1.1861 (2) | 0.3754 (2) | −0.12205 (16) | 0.0318 (6) | |
H21 | 1.203403 | 0.433689 | −0.142443 | 0.038* | |
C22 | 1.2640 (2) | 0.3447 (2) | −0.10273 (16) | 0.0347 (6) | |
H22 | 1.334332 | 0.381090 | −0.110091 | 0.042* | |
C23 | 1.2389 (2) | 0.2601 (2) | −0.07238 (15) | 0.0281 (6) | |
H23 | 1.292957 | 0.239517 | −0.057832 | 0.034* | |
C24 | 1.1356 (2) | 0.20569 (19) | −0.06327 (13) | 0.0224 (5) | |
H24 | 1.119036 | 0.147708 | −0.042656 | 0.027* | |
C25 | 0.90816 (19) | 0.24493 (18) | −0.03934 (12) | 0.0182 (5) | |
C26 | 0.80031 (19) | 0.23362 (18) | −0.07101 (13) | 0.0192 (5) | |
H26 | 0.743168 | 0.180264 | −0.116508 | 0.023* | |
C27 | 0.78689 (19) | 0.30668 (19) | −0.02979 (13) | 0.0202 (5) | |
C28 | 0.9775 (2) | 0.32913 (19) | 0.02587 (13) | 0.0200 (5) | |
C29 | 1.0976 (2) | 0.3715 (2) | 0.07450 (14) | 0.0285 (6) | |
H29A | 1.1150 (6) | 0.3142 (9) | 0.0668 (7) | 0.043* | |
H29B | 1.1075 (5) | 0.3953 (13) | 0.1279 (8) | 0.043* | |
H29C | 1.1500 (8) | 0.4332 (13) | 0.0610 (7) | 0.043* | |
C30 | 0.6885 (2) | 0.31875 (19) | −0.04461 (13) | 0.0219 (5) | |
C31 | 0.6191 (2) | 0.29644 (19) | −0.11778 (14) | 0.0232 (5) | |
H31 | 0.636545 | 0.274885 | −0.159193 | 0.028* | |
C32 | 0.5250 (2) | 0.3059 (2) | −0.12971 (15) | 0.0269 (6) | |
H32 | 0.478359 | 0.289326 | −0.180012 | 0.032* | |
C33 | 0.5627 (2) | 0.3574 (3) | −0.00408 (16) | 0.0403 (7) | |
H33 | 0.543213 | 0.378917 | 0.036199 | 0.048* | |
C34 | 0.6573 (2) | 0.3491 (2) | 0.01329 (15) | 0.0332 (6) | |
H34 | 0.700713 | 0.363884 | 0.064102 | 0.040* | |
C35 | 0.70127 (17) | 0.63152 (16) | 0.59872 (12) | 0.0128 (4) | |
C36 | 0.67163 (17) | 0.70997 (16) | 0.57665 (12) | 0.0129 (4) | |
C37 | 0.62946 (19) | 0.70311 (18) | 0.50111 (12) | 0.0167 (5) | |
H37 | 0.610420 | 0.642537 | 0.463011 | 0.020* | |
C38 | 0.61504 (19) | 0.78383 (18) | 0.48101 (13) | 0.0191 (5) | |
H38 | 0.585738 | 0.777682 | 0.429482 | 0.023* | |
C39 | 0.64325 (19) | 0.87295 (18) | 0.53585 (13) | 0.0182 (5) | |
H39 | 0.634129 | 0.928397 | 0.522235 | 0.022* | |
C40 | 0.68485 (18) | 0.88056 (17) | 0.61068 (13) | 0.0168 (5) | |
H40 | 0.704353 | 0.941572 | 0.648557 | 0.020* | |
C41 | 0.69833 (18) | 0.79991 (17) | 0.63085 (12) | 0.0144 (4) | |
H41 | 0.726237 | 0.806053 | 0.682513 | 0.017* | |
C42 | 0.74814 (17) | 0.59050 (16) | 0.55021 (11) | 0.0122 (4) | |
C43 | 0.70066 (17) | 0.47901 (16) | 0.51879 (11) | 0.0129 (4) | |
H43 | 0.635733 | 0.425432 | 0.525460 | 0.016* | |
C44 | 0.75651 (17) | 0.45540 (16) | 0.47805 (12) | 0.0131 (4) | |
C45 | 0.84041 (19) | 0.65159 (17) | 0.53194 (12) | 0.0150 (4) | |
C46 | 0.9131 (2) | 0.77190 (17) | 0.55342 (13) | 0.0211 (5) | |
H46A | 0.9895 (11) | 0.7928 (4) | 0.5575 (8) | 0.032* | |
H46B | 0.9135 (11) | 0.8030 (5) | 0.6009 (8) | 0.032* | |
H46C | 0.8827 (9) | 0.7969 (4) | 0.5156 (7) | 0.032* | |
C47 | 0.72652 (17) | 0.34925 (16) | 0.43688 (11) | 0.0118 (4) | |
C48 | 0.61775 (18) | 0.26107 (17) | 0.42126 (12) | 0.0155 (4) | |
H48 | 0.563436 | 0.271003 | 0.435692 | 0.019* | |
C49 | 0.58981 (18) | 0.15991 (17) | 0.38491 (12) | 0.0156 (4) | |
H49 | 0.515795 | 0.101077 | 0.375327 | 0.019* | |
C50 | 0.76477 (19) | 0.22477 (17) | 0.37539 (12) | 0.0157 (4) | |
H50 | 0.816509 | 0.212546 | 0.359020 | 0.019* | |
C51 | 0.79984 (19) | 0.32882 (17) | 0.41139 (12) | 0.0161 (4) | |
H51 | 0.873605 | 0.386203 | 0.418737 | 0.019* | |
C52 | 0.69324 (17) | 0.59757 (16) | 0.66037 (12) | 0.0128 (4) | |
C53 | 0.62379 (18) | 0.60669 (16) | 0.70361 (12) | 0.0135 (4) | |
C54 | 0.66154 (19) | 0.62632 (18) | 0.78145 (12) | 0.0186 (5) | |
H54 | 0.733624 | 0.636512 | 0.806680 | 0.022* | |
C55 | 0.5962 (2) | 0.6313 (2) | 0.82266 (13) | 0.0237 (5) | |
H55 | 0.623535 | 0.644918 | 0.875534 | 0.028* | |
C56 | 0.4904 (2) | 0.6161 (2) | 0.78624 (14) | 0.0235 (5) | |
H56 | 0.445601 | 0.620563 | 0.814111 | 0.028* | |
C57 | 0.45094 (19) | 0.59452 (19) | 0.70895 (13) | 0.0208 (5) | |
H57 | 0.378173 | 0.582975 | 0.683802 | 0.025* | |
C58 | 0.51624 (18) | 0.58959 (17) | 0.66807 (12) | 0.0153 (4) | |
H58 | 0.487655 | 0.574363 | 0.615084 | 0.018* | |
C59 | 0.76253 (18) | 0.55120 (17) | 0.68922 (12) | 0.0133 (4) | |
C60 | 0.88141 (18) | 0.60647 (17) | 0.70322 (12) | 0.0143 (4) | |
H60 | 0.921071 | 0.673820 | 0.694754 | 0.017* | |
C61 | 0.93324 (18) | 0.55500 (17) | 0.72962 (12) | 0.0152 (4) | |
C62 | 0.72500 (18) | 0.45633 (17) | 0.70685 (12) | 0.0166 (5) | |
C63 | 0.6085 (2) | 0.37709 (19) | 0.70262 (15) | 0.0258 (6) | |
H63A | 0.5924 (6) | 0.3047 (11) | 0.6844 (9) | 0.039* | |
H63B | 0.5531 (8) | 0.3863 (9) | 0.6684 (9) | 0.039* | |
H63C | 0.6039 (5) | 0.3886 (9) | 0.7523 (7) | 0.039* | |
C64 | 1.05431 (18) | 0.59262 (17) | 0.75030 (12) | 0.0158 (4) | |
C65 | 1.13600 (19) | 0.70208 (18) | 0.78299 (13) | 0.0199 (5) | |
H65 | 1.113207 | 0.752079 | 0.792372 | 0.024* | |
C66 | 1.2499 (2) | 0.73730 (19) | 0.80159 (14) | 0.0230 (5) | |
H66 | 1.303575 | 0.812179 | 0.823343 | 0.028* | |
C67 | 1.2107 (2) | 0.56820 (19) | 0.75998 (14) | 0.0229 (5) | |
H67 | 1.236448 | 0.520309 | 0.751728 | 0.028* | |
C68 | 1.09432 (19) | 0.52443 (18) | 0.73898 (13) | 0.0207 (5) | |
H68 | 1.042874 | 0.449167 | 0.717254 | 0.025* | |
C69 | 0.31385 (18) | −0.14621 (16) | 0.34588 (12) | 0.0142 (4) | |
C70 | 0.31622 (19) | −0.15843 (19) | 0.41618 (13) | 0.0207 (5) | |
H70 | 0.385483 | −0.140620 | 0.452877 | 0.025* | |
C71 | 0.2185 (2) | −0.19635 (19) | 0.43331 (13) | 0.0212 (5) | |
H71 | 0.220147 | −0.205114 | 0.481380 | 0.025* | |
C72 | 0.11878 (18) | −0.22123 (17) | 0.37970 (13) | 0.0150 (4) | |
C73 | 0.11424 (18) | −0.20984 (17) | 0.30919 (12) | 0.0155 (4) | |
H73 | 0.044826 | −0.227603 | 0.272692 | 0.019* | |
C74 | 0.21263 (19) | −0.17207 (17) | 0.29258 (13) | 0.0159 (4) | |
H74 | 0.210621 | −0.163877 | 0.244348 | 0.019* | |
C75 | 0.42122 (19) | −0.10342 (17) | 0.32933 (14) | 0.0186 (5) | |
C76 | −0.18768 (18) | −0.14033 (17) | 0.36415 (12) | 0.0141 (4) | |
C77 | −0.07078 (18) | −0.07122 (18) | 0.40025 (12) | 0.0160 (4) | |
H77 | −0.040010 | 0.003763 | 0.418423 | 0.019* | |
C78 | 0.00158 (19) | −0.11017 (18) | 0.41013 (13) | 0.0184 (5) | |
H78 | 0.081477 | −0.062798 | 0.434383 | 0.022* | |
C79 | −0.04586 (18) | −0.22017 (18) | 0.38363 (12) | 0.0157 (4) | |
C80 | −0.16168 (19) | −0.29013 (18) | 0.34838 (12) | 0.0175 (5) | |
H80 | −0.192352 | −0.365205 | 0.331145 | 0.021* | |
C81 | −0.23284 (19) | −0.25027 (18) | 0.33829 (12) | 0.0176 (5) | |
H81 | −0.312622 | −0.297987 | 0.313684 | 0.021* | |
C82 | −0.26513 (18) | −0.09767 (18) | 0.35014 (12) | 0.0152 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.01263 (12) | 0.01346 (12) | 0.01246 (13) | 0.00849 (10) | 0.00680 (10) | 0.00437 (10) |
S1 | 0.0159 (3) | 0.0229 (3) | 0.0135 (3) | 0.0100 (2) | 0.0058 (2) | 0.0044 (2) |
S2 | 0.0251 (3) | 0.0266 (3) | 0.0177 (3) | 0.0159 (3) | 0.0046 (2) | −0.0002 (2) |
S3 | 0.0173 (3) | 0.0127 (2) | 0.0200 (3) | 0.0076 (2) | 0.0115 (2) | 0.0057 (2) |
S4 | 0.0160 (3) | 0.0149 (3) | 0.0254 (3) | 0.0092 (2) | 0.0058 (2) | 0.0085 (2) |
O1 | 0.0193 (9) | 0.0240 (9) | 0.0407 (10) | 0.0158 (7) | 0.0171 (8) | 0.0182 (8) |
O2 | 0.0277 (9) | 0.0205 (8) | 0.0299 (10) | 0.0108 (7) | 0.0226 (8) | 0.0077 (7) |
O3 | 0.0191 (8) | 0.0245 (9) | 0.0362 (10) | 0.0172 (7) | 0.0201 (7) | 0.0217 (8) |
O4 | 0.0210 (8) | 0.0208 (8) | 0.0177 (8) | 0.0155 (7) | 0.0070 (7) | 0.0057 (7) |
O5 | 0.0155 (8) | 0.0245 (8) | 0.0216 (8) | 0.0125 (7) | 0.0076 (7) | 0.0101 (7) |
N1 | 0.0151 (9) | 0.0136 (9) | 0.0127 (9) | 0.0081 (7) | 0.0075 (7) | 0.0038 (7) |
N2 | 0.0274 (12) | 0.0490 (15) | 0.0365 (14) | 0.0251 (12) | 0.0099 (11) | 0.0034 (11) |
N3 | 0.0171 (9) | 0.0151 (9) | 0.0108 (9) | 0.0110 (8) | 0.0061 (7) | 0.0043 (7) |
N4 | 0.0182 (10) | 0.0244 (11) | 0.0286 (11) | 0.0124 (9) | 0.0091 (9) | 0.0074 (9) |
C1 | 0.0176 (11) | 0.0229 (11) | 0.0118 (11) | 0.0116 (10) | 0.0072 (9) | 0.0069 (9) |
C2 | 0.0173 (11) | 0.0195 (11) | 0.0151 (11) | 0.0104 (9) | 0.0080 (9) | 0.0061 (9) |
C3 | 0.0208 (12) | 0.0222 (12) | 0.0236 (12) | 0.0105 (10) | 0.0107 (10) | 0.0111 (10) |
C4 | 0.0206 (12) | 0.0169 (11) | 0.0327 (14) | 0.0108 (10) | 0.0094 (10) | 0.0091 (10) |
C5 | 0.0161 (11) | 0.0208 (12) | 0.0231 (12) | 0.0103 (10) | 0.0045 (9) | −0.0010 (10) |
C6 | 0.0193 (11) | 0.0236 (12) | 0.0161 (11) | 0.0112 (10) | 0.0073 (9) | 0.0041 (9) |
C7 | 0.0206 (11) | 0.0197 (11) | 0.0147 (11) | 0.0119 (10) | 0.0057 (9) | 0.0068 (9) |
C8 | 0.0202 (11) | 0.0216 (11) | 0.0145 (11) | 0.0135 (10) | 0.0097 (9) | 0.0077 (9) |
C9 | 0.0166 (11) | 0.0232 (12) | 0.0138 (11) | 0.0103 (10) | 0.0055 (9) | 0.0036 (9) |
C10 | 0.0173 (11) | 0.0212 (11) | 0.0124 (11) | 0.0124 (9) | 0.0057 (9) | 0.0042 (9) |
C11 | 0.0208 (11) | 0.0209 (11) | 0.0144 (11) | 0.0146 (10) | 0.0084 (9) | 0.0055 (9) |
C12 | 0.0259 (13) | 0.0291 (13) | 0.0145 (12) | 0.0135 (11) | 0.0065 (10) | 0.0055 (10) |
C13 | 0.0192 (11) | 0.0154 (10) | 0.0135 (11) | 0.0097 (9) | 0.0076 (9) | 0.0042 (9) |
C14 | 0.0149 (11) | 0.0269 (12) | 0.0176 (11) | 0.0118 (10) | 0.0075 (9) | 0.0064 (10) |
C15 | 0.0166 (11) | 0.0240 (12) | 0.0156 (11) | 0.0110 (10) | 0.0066 (9) | 0.0066 (9) |
C16 | 0.0166 (11) | 0.0194 (11) | 0.0189 (11) | 0.0122 (9) | 0.0088 (9) | 0.0083 (9) |
C17 | 0.0162 (11) | 0.0194 (11) | 0.0147 (11) | 0.0094 (9) | 0.0052 (9) | 0.0050 (9) |
C18 | 0.0177 (11) | 0.0250 (12) | 0.0138 (11) | 0.0134 (10) | 0.0072 (9) | 0.0080 (9) |
C19 | 0.0184 (11) | 0.0188 (11) | 0.0136 (11) | 0.0091 (9) | 0.0054 (9) | 0.0020 (9) |
C20 | 0.0216 (12) | 0.0240 (12) | 0.0256 (13) | 0.0134 (10) | 0.0083 (10) | 0.0065 (10) |
C21 | 0.0302 (14) | 0.0260 (13) | 0.0422 (16) | 0.0121 (12) | 0.0194 (13) | 0.0171 (12) |
C22 | 0.0216 (13) | 0.0355 (15) | 0.0482 (18) | 0.0128 (12) | 0.0191 (13) | 0.0126 (13) |
C23 | 0.0204 (12) | 0.0289 (14) | 0.0344 (15) | 0.0142 (11) | 0.0088 (11) | 0.0053 (11) |
C24 | 0.0223 (12) | 0.0227 (12) | 0.0225 (12) | 0.0122 (10) | 0.0080 (10) | 0.0058 (10) |
C25 | 0.0201 (11) | 0.0206 (11) | 0.0169 (11) | 0.0123 (10) | 0.0075 (9) | 0.0058 (9) |
C26 | 0.0183 (11) | 0.0217 (12) | 0.0156 (11) | 0.0094 (10) | 0.0071 (9) | 0.0025 (9) |
C27 | 0.0199 (12) | 0.0245 (12) | 0.0171 (11) | 0.0129 (10) | 0.0067 (9) | 0.0044 (10) |
C28 | 0.0228 (12) | 0.0235 (12) | 0.0174 (12) | 0.0147 (10) | 0.0084 (10) | 0.0053 (10) |
C29 | 0.0277 (14) | 0.0353 (15) | 0.0214 (13) | 0.0192 (12) | 0.0049 (11) | 0.0030 (11) |
C30 | 0.0205 (12) | 0.0221 (12) | 0.0224 (12) | 0.0110 (10) | 0.0089 (10) | 0.0036 (10) |
C31 | 0.0251 (13) | 0.0253 (13) | 0.0221 (12) | 0.0152 (11) | 0.0101 (10) | 0.0047 (10) |
C32 | 0.0242 (13) | 0.0264 (13) | 0.0291 (14) | 0.0137 (11) | 0.0084 (11) | 0.0062 (11) |
C33 | 0.0378 (16) | 0.058 (2) | 0.0287 (15) | 0.0318 (16) | 0.0123 (13) | −0.0013 (14) |
C34 | 0.0305 (14) | 0.0463 (17) | 0.0246 (14) | 0.0244 (13) | 0.0090 (11) | 0.0021 (12) |
C35 | 0.0123 (10) | 0.0116 (10) | 0.0143 (11) | 0.0066 (8) | 0.0041 (8) | 0.0031 (8) |
C36 | 0.0108 (10) | 0.0141 (10) | 0.0151 (11) | 0.0068 (8) | 0.0060 (8) | 0.0043 (8) |
C37 | 0.0196 (11) | 0.0171 (11) | 0.0148 (11) | 0.0105 (9) | 0.0066 (9) | 0.0044 (9) |
C38 | 0.0205 (11) | 0.0239 (12) | 0.0171 (11) | 0.0134 (10) | 0.0070 (9) | 0.0107 (10) |
C39 | 0.0182 (11) | 0.0179 (11) | 0.0250 (12) | 0.0125 (9) | 0.0092 (10) | 0.0108 (10) |
C40 | 0.0163 (11) | 0.0155 (11) | 0.0214 (12) | 0.0103 (9) | 0.0077 (9) | 0.0043 (9) |
C41 | 0.0138 (10) | 0.0161 (10) | 0.0149 (11) | 0.0084 (9) | 0.0067 (8) | 0.0046 (9) |
C42 | 0.0139 (10) | 0.0135 (10) | 0.0123 (10) | 0.0091 (9) | 0.0047 (8) | 0.0057 (8) |
C43 | 0.0132 (10) | 0.0136 (10) | 0.0139 (10) | 0.0080 (8) | 0.0050 (8) | 0.0058 (8) |
C44 | 0.0129 (10) | 0.0137 (10) | 0.0137 (10) | 0.0073 (8) | 0.0047 (8) | 0.0059 (8) |
C45 | 0.0208 (11) | 0.0128 (10) | 0.0147 (11) | 0.0098 (9) | 0.0090 (9) | 0.0046 (8) |
C46 | 0.0242 (12) | 0.0150 (11) | 0.0248 (13) | 0.0082 (10) | 0.0146 (10) | 0.0052 (10) |
C47 | 0.0152 (10) | 0.0140 (10) | 0.0095 (10) | 0.0094 (9) | 0.0044 (8) | 0.0058 (8) |
C48 | 0.0150 (10) | 0.0175 (11) | 0.0164 (11) | 0.0108 (9) | 0.0057 (9) | 0.0038 (9) |
C49 | 0.0135 (10) | 0.0172 (11) | 0.0153 (11) | 0.0087 (9) | 0.0035 (8) | 0.0032 (9) |
C50 | 0.0193 (11) | 0.0201 (11) | 0.0157 (11) | 0.0134 (9) | 0.0111 (9) | 0.0077 (9) |
C51 | 0.0166 (11) | 0.0159 (11) | 0.0183 (11) | 0.0083 (9) | 0.0098 (9) | 0.0068 (9) |
C52 | 0.0107 (10) | 0.0097 (9) | 0.0155 (11) | 0.0046 (8) | 0.0035 (8) | 0.0019 (8) |
C53 | 0.0137 (10) | 0.0133 (10) | 0.0167 (11) | 0.0084 (9) | 0.0068 (9) | 0.0056 (9) |
C54 | 0.0168 (11) | 0.0265 (12) | 0.0165 (11) | 0.0145 (10) | 0.0056 (9) | 0.0071 (10) |
C55 | 0.0269 (13) | 0.0355 (14) | 0.0156 (12) | 0.0197 (11) | 0.0108 (10) | 0.0094 (10) |
C56 | 0.0246 (13) | 0.0332 (14) | 0.0252 (13) | 0.0204 (11) | 0.0157 (11) | 0.0117 (11) |
C57 | 0.0159 (11) | 0.0284 (13) | 0.0239 (13) | 0.0149 (10) | 0.0065 (10) | 0.0129 (10) |
C58 | 0.0157 (10) | 0.0179 (11) | 0.0139 (11) | 0.0091 (9) | 0.0056 (9) | 0.0075 (9) |
C59 | 0.0150 (10) | 0.0147 (10) | 0.0113 (10) | 0.0090 (9) | 0.0053 (8) | 0.0017 (8) |
C60 | 0.0170 (11) | 0.0142 (10) | 0.0158 (11) | 0.0096 (9) | 0.0088 (9) | 0.0050 (9) |
C61 | 0.0162 (10) | 0.0139 (10) | 0.0159 (11) | 0.0082 (9) | 0.0063 (9) | 0.0039 (9) |
C62 | 0.0162 (11) | 0.0181 (11) | 0.0162 (11) | 0.0100 (9) | 0.0048 (9) | 0.0054 (9) |
C63 | 0.0168 (12) | 0.0225 (12) | 0.0362 (15) | 0.0083 (10) | 0.0077 (11) | 0.0150 (11) |
C64 | 0.0177 (11) | 0.0179 (11) | 0.0157 (11) | 0.0109 (9) | 0.0076 (9) | 0.0067 (9) |
C65 | 0.0192 (11) | 0.0187 (11) | 0.0255 (13) | 0.0129 (10) | 0.0077 (10) | 0.0065 (10) |
C66 | 0.0183 (12) | 0.0203 (12) | 0.0297 (13) | 0.0105 (10) | 0.0070 (10) | 0.0073 (10) |
C67 | 0.0208 (12) | 0.0251 (12) | 0.0291 (13) | 0.0164 (10) | 0.0105 (10) | 0.0065 (10) |
C68 | 0.0188 (11) | 0.0187 (11) | 0.0256 (13) | 0.0118 (10) | 0.0072 (10) | 0.0037 (10) |
C69 | 0.0174 (11) | 0.0110 (10) | 0.0213 (12) | 0.0097 (9) | 0.0120 (9) | 0.0077 (9) |
C70 | 0.0166 (11) | 0.0267 (12) | 0.0241 (13) | 0.0134 (10) | 0.0086 (10) | 0.0125 (10) |
C71 | 0.0244 (12) | 0.0320 (13) | 0.0171 (12) | 0.0175 (11) | 0.0131 (10) | 0.0147 (10) |
C72 | 0.0157 (10) | 0.0165 (10) | 0.0227 (12) | 0.0114 (9) | 0.0131 (9) | 0.0112 (9) |
C73 | 0.0158 (11) | 0.0175 (11) | 0.0176 (11) | 0.0116 (9) | 0.0061 (9) | 0.0072 (9) |
C74 | 0.0229 (12) | 0.0157 (10) | 0.0178 (11) | 0.0130 (9) | 0.0131 (9) | 0.0084 (9) |
C75 | 0.0218 (12) | 0.0111 (10) | 0.0340 (14) | 0.0116 (9) | 0.0193 (11) | 0.0098 (10) |
C76 | 0.0158 (10) | 0.0186 (11) | 0.0135 (11) | 0.0107 (9) | 0.0089 (9) | 0.0072 (9) |
C77 | 0.0170 (11) | 0.0161 (10) | 0.0187 (11) | 0.0097 (9) | 0.0095 (9) | 0.0064 (9) |
C78 | 0.0132 (10) | 0.0213 (11) | 0.0240 (12) | 0.0091 (9) | 0.0094 (9) | 0.0106 (10) |
C79 | 0.0181 (11) | 0.0212 (11) | 0.0197 (11) | 0.0147 (9) | 0.0128 (9) | 0.0120 (9) |
C80 | 0.0215 (11) | 0.0152 (11) | 0.0199 (12) | 0.0113 (9) | 0.0096 (9) | 0.0064 (9) |
C81 | 0.0155 (11) | 0.0195 (11) | 0.0178 (11) | 0.0098 (9) | 0.0050 (9) | 0.0055 (9) |
C82 | 0.0189 (11) | 0.0218 (11) | 0.0139 (11) | 0.0134 (10) | 0.0111 (9) | 0.0102 (9) |
Zn1—O1 | 2.0695 (16) | C32—H32 | 0.9500 |
Zn1—O2 | 2.3124 (17) | C33—H33 | 0.9500 |
Zn1—O4i | 2.1255 (15) | C33—C34 | 1.375 (4) |
Zn1—O5i | 2.2084 (15) | C34—H34 | 0.9500 |
Zn1—N1 | 2.0864 (17) | C35—C36 | 1.489 (3) |
Zn1—N3 | 2.1074 (17) | C35—C42 | 1.491 (3) |
Zn1—C75 | 2.513 (2) | C35—C52 | 1.364 (3) |
Zn1—C82i | 2.483 (2) | C36—C37 | 1.400 (3) |
S1—C10 | 1.726 (2) | C36—C41 | 1.393 (3) |
S1—C11 | 1.721 (2) | C37—H37 | 0.9500 |
S2—C27 | 1.734 (2) | C37—C38 | 1.393 (3) |
S2—C28 | 1.723 (2) | C38—H38 | 0.9500 |
S3—C44 | 1.731 (2) | C38—C39 | 1.384 (3) |
S3—C45 | 1.726 (2) | C39—H39 | 0.9500 |
S4—C61 | 1.732 (2) | C39—C40 | 1.383 (3) |
S4—C62 | 1.730 (2) | C40—H40 | 0.9500 |
O1—C75 | 1.265 (3) | C40—C41 | 1.386 (3) |
O2—C75 | 1.256 (3) | C41—H41 | 0.9500 |
O3—C72 | 1.386 (2) | C42—C43 | 1.418 (3) |
O3—C79 | 1.392 (3) | C42—C45 | 1.371 (3) |
O4—C82 | 1.269 (3) | C43—H43 | 0.9500 |
O5—C82 | 1.258 (3) | C43—C44 | 1.367 (3) |
N1—C15 | 1.348 (3) | C44—C47 | 1.458 (3) |
N1—C16 | 1.335 (3) | C45—C46 | 1.504 (3) |
N2—C32 | 1.334 (3) | C46—H46A | 0.962 (13) |
N2—C33 | 1.345 (4) | C46—H46B | 0.962 (13) |
N3—C49 | 1.342 (3) | C46—H46C | 0.962 (13) |
N3—C50 | 1.337 (3) | C47—C48 | 1.400 (3) |
N4—C66 | 1.334 (3) | C47—C51 | 1.392 (3) |
N4—C67 | 1.333 (3) | C48—H48 | 0.9500 |
C1—C2 | 1.495 (3) | C48—C49 | 1.376 (3) |
C1—C8 | 1.490 (3) | C49—H49 | 0.9500 |
C1—C18 | 1.355 (3) | C50—H50 | 0.9500 |
C2—C3 | 1.395 (3) | C50—C51 | 1.380 (3) |
C2—C7 | 1.393 (3) | C51—H51 | 0.9500 |
C3—H3 | 0.9500 | C52—C53 | 1.483 (3) |
C3—C4 | 1.388 (3) | C52—C59 | 1.493 (3) |
C4—H4 | 0.9500 | C53—C54 | 1.399 (3) |
C4—C5 | 1.383 (3) | C53—C58 | 1.398 (3) |
C5—H5 | 0.9500 | C54—H54 | 0.9500 |
C5—C6 | 1.382 (3) | C54—C55 | 1.387 (3) |
C6—H6 | 0.9500 | C55—H55 | 0.9500 |
C6—C7 | 1.380 (3) | C55—C56 | 1.390 (3) |
C7—H7 | 0.9500 | C56—H56 | 0.9500 |
C8—C9 | 1.416 (3) | C56—C57 | 1.386 (3) |
C8—C11 | 1.375 (3) | C57—H57 | 0.9500 |
C9—H9 | 0.9500 | C57—C58 | 1.381 (3) |
C9—C10 | 1.369 (3) | C58—H58 | 0.9500 |
C10—C13 | 1.460 (3) | C59—C60 | 1.424 (3) |
C11—C12 | 1.496 (3) | C59—C62 | 1.375 (3) |
C12—H12A | 0.970 (14) | C60—H60 | 0.9500 |
C12—H12B | 0.970 (14) | C60—C61 | 1.355 (3) |
C12—H12C | 0.970 (14) | C61—C64 | 1.465 (3) |
C13—C14 | 1.391 (3) | C62—C63 | 1.491 (3) |
C13—C17 | 1.393 (3) | C63—H63A | 0.973 (14) |
C14—H14 | 0.9500 | C63—H63B | 0.973 (14) |
C14—C15 | 1.372 (3) | C63—H63C | 0.973 (14) |
C15—H15 | 0.9500 | C64—C65 | 1.398 (3) |
C16—H16 | 0.9500 | C64—C68 | 1.390 (3) |
C16—C17 | 1.384 (3) | C65—H65 | 0.9500 |
C17—H17 | 0.9500 | C65—C66 | 1.380 (3) |
C18—C19 | 1.492 (3) | C66—H66 | 0.9500 |
C18—C25 | 1.488 (3) | C67—H67 | 0.9500 |
C19—C20 | 1.397 (3) | C67—C68 | 1.388 (3) |
C19—C24 | 1.398 (3) | C68—H68 | 0.9500 |
C20—H20 | 0.9500 | C69—C70 | 1.387 (3) |
C20—C21 | 1.385 (3) | C69—C74 | 1.386 (3) |
C21—H21 | 0.9500 | C69—C75 | 1.497 (3) |
C21—C22 | 1.377 (4) | C70—H70 | 0.9500 |
C22—H22 | 0.9500 | C70—C71 | 1.385 (3) |
C22—C23 | 1.389 (4) | C71—H71 | 0.9500 |
C23—H23 | 0.9500 | C71—C72 | 1.378 (3) |
C23—C24 | 1.382 (3) | C72—C73 | 1.383 (3) |
C24—H24 | 0.9500 | C73—H73 | 0.9500 |
C25—C26 | 1.425 (3) | C73—C74 | 1.387 (3) |
C25—C28 | 1.376 (3) | C74—H74 | 0.9500 |
C26—H26 | 0.9500 | C76—C77 | 1.391 (3) |
C26—C27 | 1.365 (3) | C76—C81 | 1.392 (3) |
C27—C30 | 1.461 (3) | C76—C82 | 1.499 (3) |
C28—C29 | 1.496 (3) | C77—H77 | 0.9500 |
C29—H29A | 0.992 (15) | C77—C78 | 1.388 (3) |
C29—H29B | 0.992 (15) | C78—H78 | 0.9500 |
C29—H29C | 0.992 (15) | C78—C79 | 1.388 (3) |
C30—C31 | 1.395 (3) | C79—C80 | 1.379 (3) |
C30—C34 | 1.393 (3) | C80—H80 | 0.9500 |
C31—H31 | 0.9500 | C80—C81 | 1.383 (3) |
C31—C32 | 1.382 (3) | C81—H81 | 0.9500 |
O1—Zn1—O2 | 59.92 (6) | C52—C35—C42 | 117.79 (18) |
O1—Zn1—O4i | 109.10 (6) | C37—C36—C35 | 121.21 (19) |
O1—Zn1—O5i | 89.25 (6) | C41—C36—C35 | 120.51 (19) |
O1—Zn1—N1 | 149.70 (7) | C41—C36—C37 | 117.8 (2) |
O1—Zn1—N3 | 93.03 (7) | C36—C37—H37 | 119.5 |
O1—Zn1—C75 | 30.11 (7) | C38—C37—C36 | 120.9 (2) |
O1—Zn1—C82i | 101.27 (6) | C38—C37—H37 | 119.5 |
O2—Zn1—C75 | 29.81 (7) | C37—C38—H38 | 119.9 |
O2—Zn1—C82i | 133.73 (7) | C39—C38—C37 | 120.2 (2) |
O4i—Zn1—O2 | 162.67 (6) | C39—C38—H38 | 119.9 |
O4i—Zn1—O5i | 61.10 (6) | C38—C39—H39 | 120.3 |
O4i—Zn1—C75 | 137.99 (7) | C40—C39—C38 | 119.4 (2) |
O4i—Zn1—C82i | 30.73 (6) | C40—C39—H39 | 120.3 |
O5i—Zn1—O2 | 103.65 (6) | C39—C40—H40 | 119.7 |
O5i—Zn1—C75 | 97.82 (6) | C39—C40—C41 | 120.5 (2) |
O5i—Zn1—C82i | 30.39 (6) | C41—C40—H40 | 119.7 |
N1—Zn1—O2 | 91.08 (6) | C36—C41—H41 | 119.4 |
N1—Zn1—O4i | 96.65 (6) | C40—C41—C36 | 121.1 (2) |
N1—Zn1—O5i | 89.51 (6) | C40—C41—H41 | 119.4 |
N1—Zn1—N3 | 100.05 (7) | C43—C42—C35 | 121.73 (18) |
N1—Zn1—C75 | 120.54 (8) | C45—C42—C35 | 126.22 (19) |
N1—Zn1—C82i | 92.68 (7) | C45—C42—C43 | 112.03 (18) |
N3—Zn1—O2 | 97.90 (6) | C42—C43—H43 | 122.9 |
N3—Zn1—O4i | 96.00 (6) | C44—C43—C42 | 114.11 (19) |
N3—Zn1—O5i | 156.26 (6) | C44—C43—H43 | 122.9 |
N3—Zn1—C75 | 95.91 (7) | C43—C44—S3 | 110.23 (16) |
N3—Zn1—C82i | 126.60 (7) | C43—C44—C47 | 127.29 (19) |
C82i—Zn1—C75 | 121.20 (7) | C47—C44—S3 | 122.45 (16) |
C11—S1—C10 | 92.48 (11) | C42—C45—S3 | 111.40 (16) |
C28—S2—C27 | 92.74 (11) | C42—C45—C46 | 128.4 (2) |
C45—S3—C44 | 92.21 (10) | C46—C45—S3 | 120.19 (16) |
C62—S4—C61 | 92.51 (11) | C45—C46—H46A | 109.5 |
C75—O1—Zn1 | 94.72 (14) | C45—C46—H46B | 109.5 |
C75—O2—Zn1 | 83.95 (14) | C45—C46—H46C | 109.5 |
C72—O3—C79 | 117.60 (16) | H46A—C46—H46B | 109.5 |
C82—O4—Zn1ii | 90.41 (13) | H46A—C46—H46C | 109.5 |
C82—O5—Zn1ii | 86.97 (13) | H46B—C46—H46C | 109.5 |
C15—N1—Zn1 | 118.38 (15) | C48—C47—C44 | 119.17 (19) |
C16—N1—Zn1 | 124.22 (15) | C51—C47—C44 | 124.09 (19) |
C16—N1—C15 | 117.01 (19) | C51—C47—C48 | 116.74 (19) |
C32—N2—C33 | 116.4 (2) | C47—C48—H48 | 120.1 |
C49—N3—Zn1 | 118.98 (14) | C49—C48—C47 | 119.7 (2) |
C50—N3—Zn1 | 123.70 (14) | C49—C48—H48 | 120.1 |
C50—N3—C49 | 117.03 (18) | N3—C49—C48 | 123.3 (2) |
C67—N4—C66 | 115.9 (2) | N3—C49—H49 | 118.4 |
C8—C1—C2 | 116.99 (19) | C48—C49—H49 | 118.4 |
C18—C1—C2 | 121.3 (2) | N3—C50—H50 | 118.2 |
C18—C1—C8 | 121.6 (2) | N3—C50—C51 | 123.5 (2) |
C3—C2—C1 | 121.5 (2) | C51—C50—H50 | 118.2 |
C7—C2—C1 | 120.3 (2) | C47—C51—H51 | 120.2 |
C7—C2—C3 | 118.2 (2) | C50—C51—C47 | 119.6 (2) |
C2—C3—H3 | 119.7 | C50—C51—H51 | 120.2 |
C4—C3—C2 | 120.7 (2) | C35—C52—C53 | 125.13 (19) |
C4—C3—H3 | 119.7 | C35—C52—C59 | 118.34 (19) |
C3—C4—H4 | 120.1 | C53—C52—C59 | 116.49 (18) |
C5—C4—C3 | 119.9 (2) | C54—C53—C52 | 120.51 (19) |
C5—C4—H4 | 120.1 | C58—C53—C52 | 121.64 (19) |
C4—C5—H5 | 119.9 | C58—C53—C54 | 117.74 (19) |
C6—C5—C4 | 120.2 (2) | C53—C54—H54 | 119.2 |
C6—C5—H5 | 119.9 | C55—C54—C53 | 121.5 (2) |
C5—C6—H6 | 120.2 | C55—C54—H54 | 119.2 |
C7—C6—C5 | 119.6 (2) | C54—C55—H55 | 120.2 |
C7—C6—H6 | 120.2 | C54—C55—C56 | 119.7 (2) |
C2—C7—H7 | 119.3 | C56—C55—H55 | 120.2 |
C6—C7—C2 | 121.3 (2) | C55—C56—H56 | 120.3 |
C6—C7—H7 | 119.3 | C57—C56—C55 | 119.4 (2) |
C9—C8—C1 | 122.4 (2) | C57—C56—H56 | 120.3 |
C11—C8—C1 | 125.7 (2) | C56—C57—H57 | 119.6 |
C11—C8—C9 | 111.9 (2) | C58—C57—C56 | 120.7 (2) |
C8—C9—H9 | 122.9 | C58—C57—H57 | 119.6 |
C10—C9—C8 | 114.1 (2) | C53—C58—H58 | 119.6 |
C10—C9—H9 | 122.9 | C57—C58—C53 | 120.9 (2) |
C9—C10—S1 | 110.16 (16) | C57—C58—H58 | 119.6 |
C9—C10—C13 | 126.6 (2) | C60—C59—C52 | 120.98 (19) |
C13—C10—S1 | 123.20 (17) | C62—C59—C52 | 126.95 (19) |
C8—C11—S1 | 111.31 (16) | C62—C59—C60 | 112.05 (19) |
C8—C11—C12 | 128.8 (2) | C59—C60—H60 | 122.8 |
C12—C11—S1 | 119.83 (17) | C61—C60—C59 | 114.4 (2) |
C11—C12—H12A | 109.5 | C61—C60—H60 | 122.8 |
C11—C12—H12B | 109.5 | C60—C61—S4 | 110.21 (16) |
C11—C12—H12C | 109.5 | C60—C61—C64 | 126.9 (2) |
H12A—C12—H12B | 109.5 | C64—C61—S4 | 122.89 (16) |
H12A—C12—H12C | 109.5 | C59—C62—S4 | 110.76 (16) |
H12B—C12—H12C | 109.5 | C59—C62—C63 | 128.9 (2) |
C14—C13—C10 | 119.3 (2) | C63—C62—S4 | 120.30 (17) |
C14—C13—C17 | 117.1 (2) | C62—C63—H63A | 109.5 |
C17—C13—C10 | 123.6 (2) | C62—C63—H63B | 109.5 |
C13—C14—H14 | 120.1 | C62—C63—H63C | 109.5 |
C15—C14—C13 | 119.9 (2) | H63A—C63—H63B | 109.5 |
C15—C14—H14 | 120.1 | H63A—C63—H63C | 109.5 |
N1—C15—C14 | 123.2 (2) | H63B—C63—H63C | 109.5 |
N1—C15—H15 | 118.4 | C65—C64—C61 | 119.97 (19) |
C14—C15—H15 | 118.4 | C68—C64—C61 | 123.3 (2) |
N1—C16—H16 | 118.3 | C68—C64—C65 | 116.7 (2) |
N1—C16—C17 | 123.4 (2) | C64—C65—H65 | 120.1 |
C17—C16—H16 | 118.3 | C66—C65—C64 | 119.8 (2) |
C13—C17—H17 | 120.3 | C66—C65—H65 | 120.1 |
C16—C17—C13 | 119.4 (2) | N4—C66—C65 | 124.0 (2) |
C16—C17—H17 | 120.3 | N4—C66—H66 | 118.0 |
C1—C18—C19 | 122.7 (2) | C65—C66—H66 | 118.0 |
C1—C18—C25 | 122.3 (2) | N4—C67—H67 | 117.6 |
C25—C18—C19 | 114.96 (19) | N4—C67—C68 | 124.8 (2) |
C20—C19—C18 | 120.3 (2) | C68—C67—H67 | 117.6 |
C20—C19—C24 | 118.4 (2) | C64—C68—H68 | 120.6 |
C24—C19—C18 | 121.3 (2) | C67—C68—C64 | 118.8 (2) |
C19—C20—H20 | 119.8 | C67—C68—H68 | 120.6 |
C21—C20—C19 | 120.3 (2) | C70—C69—C75 | 119.4 (2) |
C21—C20—H20 | 119.8 | C74—C69—C70 | 119.5 (2) |
C20—C21—H21 | 119.6 | C74—C69—C75 | 121.1 (2) |
C22—C21—C20 | 120.8 (2) | C69—C70—H70 | 119.7 |
C22—C21—H21 | 119.6 | C71—C70—C69 | 120.6 (2) |
C21—C22—H22 | 120.3 | C71—C70—H70 | 119.7 |
C21—C22—C23 | 119.4 (2) | C70—C71—H71 | 120.4 |
C23—C22—H22 | 120.3 | C72—C71—C70 | 119.1 (2) |
C22—C23—H23 | 119.9 | C72—C71—H71 | 120.4 |
C24—C23—C22 | 120.2 (2) | C71—C72—O3 | 117.71 (19) |
C24—C23—H23 | 119.9 | C71—C72—C73 | 121.4 (2) |
C19—C24—H24 | 119.6 | C73—C72—O3 | 120.74 (19) |
C23—C24—C19 | 120.8 (2) | C72—C73—H73 | 120.5 |
C23—C24—H24 | 119.6 | C72—C73—C74 | 119.0 (2) |
C26—C25—C18 | 122.9 (2) | C74—C73—H73 | 120.5 |
C28—C25—C18 | 124.4 (2) | C69—C74—C73 | 120.5 (2) |
C28—C25—C26 | 112.6 (2) | C69—C74—H74 | 119.8 |
C25—C26—H26 | 123.2 | C73—C74—H74 | 119.8 |
C27—C26—C25 | 113.7 (2) | O1—C75—Zn1 | 55.17 (11) |
C27—C26—H26 | 123.2 | O1—C75—C69 | 118.3 (2) |
C26—C27—S2 | 110.26 (17) | O2—C75—Zn1 | 66.24 (12) |
C26—C27—C30 | 128.8 (2) | O2—C75—O1 | 121.4 (2) |
C30—C27—S2 | 120.94 (17) | O2—C75—C69 | 120.3 (2) |
C25—C28—S2 | 110.72 (17) | C69—C75—Zn1 | 172.88 (18) |
C25—C28—C29 | 129.9 (2) | C77—C76—C81 | 119.5 (2) |
C29—C28—S2 | 119.33 (17) | C77—C76—C82 | 120.89 (19) |
C28—C29—H29A | 109.5 | C81—C76—C82 | 119.57 (19) |
C28—C29—H29B | 109.5 | C76—C77—H77 | 119.5 |
C28—C29—H29C | 109.5 | C78—C77—C76 | 121.0 (2) |
H29A—C29—H29B | 109.5 | C78—C77—H77 | 119.5 |
H29A—C29—H29C | 109.5 | C77—C78—H78 | 120.9 |
H29B—C29—H29C | 109.5 | C77—C78—C79 | 118.2 (2) |
C31—C30—C27 | 121.3 (2) | C79—C78—H78 | 120.9 |
C34—C30—C27 | 121.7 (2) | C78—C79—O3 | 121.0 (2) |
C34—C30—C31 | 117.0 (2) | C80—C79—O3 | 117.11 (19) |
C30—C31—H31 | 120.2 | C80—C79—C78 | 121.7 (2) |
C32—C31—C30 | 119.7 (2) | C79—C80—H80 | 120.2 |
C32—C31—H31 | 120.2 | C79—C80—C81 | 119.6 (2) |
N2—C32—C31 | 123.5 (2) | C81—C80—H80 | 120.2 |
N2—C32—H32 | 118.2 | C76—C81—H81 | 120.0 |
C31—C32—H32 | 118.2 | C80—C81—C76 | 120.1 (2) |
N2—C33—H33 | 117.9 | C80—C81—H81 | 120.0 |
N2—C33—C34 | 124.3 (3) | O4—C82—Zn1ii | 58.86 (11) |
C34—C33—H33 | 117.9 | O4—C82—C76 | 119.70 (19) |
C30—C34—H34 | 120.4 | O5—C82—Zn1ii | 62.64 (11) |
C33—C34—C30 | 119.1 (3) | O5—C82—O4 | 121.4 (2) |
C33—C34—H34 | 120.4 | O5—C82—C76 | 118.82 (19) |
C36—C35—C42 | 116.31 (18) | C76—C82—Zn1ii | 174.88 (15) |
C52—C35—C36 | 125.85 (19) | ||
Zn1—O1—C75—O2 | 1.5 (2) | C35—C42—C43—C44 | −177.70 (19) |
Zn1—O1—C75—C69 | −176.63 (16) | C35—C42—C45—S3 | 176.85 (17) |
Zn1—O2—C75—O1 | −1.4 (2) | C35—C42—C45—C46 | −2.2 (4) |
Zn1—O2—C75—C69 | 176.75 (18) | C35—C52—C53—C54 | −145.2 (2) |
Zn1ii—O4—C82—O5 | −3.1 (2) | C35—C52—C53—C58 | 38.8 (3) |
Zn1ii—O4—C82—C76 | 174.30 (17) | C35—C52—C59—C60 | 50.8 (3) |
Zn1ii—O5—C82—O4 | 3.0 (2) | C35—C52—C59—C62 | −130.7 (2) |
Zn1ii—O5—C82—C76 | −174.43 (17) | C36—C35—C42—C43 | −127.1 (2) |
Zn1—N1—C15—C14 | 173.79 (17) | C36—C35—C42—C45 | 54.7 (3) |
Zn1—N1—C16—C17 | −173.21 (16) | C36—C35—C52—C53 | 18.9 (3) |
Zn1—N3—C49—C48 | 172.91 (16) | C36—C35—C52—C59 | −158.63 (19) |
Zn1—N3—C50—C51 | −172.66 (16) | C36—C37—C38—C39 | 0.5 (3) |
S1—C10—C13—C14 | 150.10 (18) | C37—C36—C41—C40 | −0.7 (3) |
S1—C10—C13—C17 | −31.5 (3) | C37—C38—C39—C40 | −0.6 (3) |
S2—C27—C30—C31 | 146.2 (2) | C38—C39—C40—C41 | 0.0 (3) |
S2—C27—C30—C34 | −36.2 (3) | C39—C40—C41—C36 | 0.7 (3) |
S3—C44—C47—C48 | −162.17 (16) | C41—C36—C37—C38 | 0.1 (3) |
S3—C44—C47—C51 | 17.8 (3) | C42—C35—C36—C37 | 34.0 (3) |
S4—C61—C64—C65 | −144.42 (19) | C42—C35—C36—C41 | −138.0 (2) |
S4—C61—C64—C68 | 35.8 (3) | C42—C35—C52—C53 | −163.73 (19) |
O3—C72—C73—C74 | −175.87 (19) | C42—C35—C52—C59 | 18.8 (3) |
O3—C79—C80—C81 | 175.65 (19) | C42—C43—C44—S3 | 0.4 (2) |
N1—C16—C17—C13 | −0.7 (3) | C42—C43—C44—C47 | −177.69 (19) |
N2—C33—C34—C30 | 0.7 (5) | C43—C42—C45—S3 | −1.5 (2) |
N3—C50—C51—C47 | 0.8 (3) | C43—C42—C45—C46 | 179.4 (2) |
N4—C67—C68—C64 | 0.1 (4) | C43—C44—C47—C48 | 15.7 (3) |
C1—C2—C3—C4 | −175.0 (2) | C43—C44—C47—C51 | −164.4 (2) |
C1—C2—C7—C6 | 175.3 (2) | C44—S3—C45—C42 | 1.49 (17) |
C1—C8—C9—C10 | −179.9 (2) | C44—S3—C45—C46 | −179.34 (19) |
C1—C8—C11—S1 | 179.53 (18) | C44—C47—C48—C49 | −177.59 (19) |
C1—C8—C11—C12 | −2.8 (4) | C44—C47—C51—C50 | 177.5 (2) |
C1—C18—C19—C20 | 131.4 (2) | C45—S3—C44—C43 | −1.04 (17) |
C1—C18—C19—C24 | −49.5 (3) | C45—S3—C44—C47 | 177.12 (18) |
C1—C18—C25—C26 | −49.0 (3) | C45—C42—C43—C44 | 0.8 (3) |
C1—C18—C25—C28 | 134.0 (2) | C47—C48—C49—N3 | −0.7 (3) |
C2—C1—C8—C9 | 124.9 (2) | C48—C47—C51—C50 | −2.5 (3) |
C2—C1—C8—C11 | −53.3 (3) | C49—N3—C50—C51 | 1.1 (3) |
C2—C1—C18—C19 | −7.9 (3) | C50—N3—C49—C48 | −1.1 (3) |
C2—C1—C18—C25 | 170.1 (2) | C51—C47—C48—C49 | 2.4 (3) |
C2—C3—C4—C5 | −1.4 (4) | C52—C35—C36—C37 | −148.6 (2) |
C3—C2—C7—C6 | −2.9 (3) | C52—C35—C36—C41 | 39.4 (3) |
C3—C4—C5—C6 | −0.9 (3) | C52—C35—C42—C43 | 55.3 (3) |
C4—C5—C6—C7 | 1.2 (3) | C52—C35—C42—C45 | −122.9 (2) |
C5—C6—C7—C2 | 0.7 (3) | C52—C53—C54—C55 | −177.6 (2) |
C7—C2—C3—C4 | 3.2 (3) | C52—C53—C58—C57 | 177.6 (2) |
C8—C1—C2—C3 | −44.6 (3) | C52—C59—C60—C61 | 179.69 (19) |
C8—C1—C2—C7 | 137.3 (2) | C52—C59—C62—S4 | 179.28 (17) |
C8—C1—C18—C19 | 168.5 (2) | C52—C59—C62—C63 | −0.6 (4) |
C8—C1—C18—C25 | −13.4 (3) | C53—C52—C59—C60 | −127.0 (2) |
C8—C9—C10—S1 | 1.1 (3) | C53—C52—C59—C62 | 51.6 (3) |
C8—C9—C10—C13 | −178.9 (2) | C53—C54—C55—C56 | 0.2 (4) |
C9—C8—C11—S1 | 1.2 (2) | C54—C53—C58—C57 | 1.5 (3) |
C9—C8—C11—C12 | 178.8 (2) | C54—C55—C56—C57 | 1.1 (4) |
C9—C10—C13—C14 | −30.0 (3) | C55—C56—C57—C58 | −1.0 (4) |
C9—C10—C13—C17 | 148.4 (2) | C56—C57—C58—C53 | −0.3 (3) |
C10—S1—C11—C8 | −0.51 (18) | C58—C53—C54—C55 | −1.5 (3) |
C10—S1—C11—C12 | −178.38 (19) | C59—C52—C53—C54 | 32.4 (3) |
C10—C13—C14—C15 | 176.9 (2) | C59—C52—C53—C58 | −143.6 (2) |
C10—C13—C17—C16 | −176.7 (2) | C59—C60—C61—S4 | 0.6 (2) |
C11—S1—C10—C9 | −0.31 (18) | C59—C60—C61—C64 | −178.8 (2) |
C11—S1—C10—C13 | 179.61 (19) | C60—C59—C62—S4 | −2.1 (2) |
C11—C8—C9—C10 | −1.5 (3) | C60—C59—C62—C63 | 178.0 (2) |
C13—C14—C15—N1 | 0.4 (3) | C60—C61—C64—C65 | 35.0 (3) |
C14—C13—C17—C16 | 1.7 (3) | C60—C61—C64—C68 | −144.9 (2) |
C15—N1—C16—C17 | −0.6 (3) | C61—S4—C62—C59 | 2.08 (18) |
C16—N1—C15—C14 | 0.7 (3) | C61—S4—C62—C63 | −178.0 (2) |
C17—C13—C14—C15 | −1.6 (3) | C61—C64—C65—C66 | −179.3 (2) |
C18—C1—C2—C3 | 132.0 (2) | C61—C64—C68—C67 | 179.5 (2) |
C18—C1—C2—C7 | −46.1 (3) | C62—S4—C61—C60 | −1.53 (18) |
C18—C1—C8—C9 | −51.7 (3) | C62—S4—C61—C64 | 177.95 (19) |
C18—C1—C8—C11 | 130.1 (2) | C62—C59—C60—C61 | 1.0 (3) |
C18—C19—C20—C21 | −178.1 (2) | C64—C65—C66—N4 | −0.5 (4) |
C18—C19—C24—C23 | 179.0 (2) | C65—C64—C68—C67 | −0.4 (3) |
C18—C25—C26—C27 | −178.5 (2) | C66—N4—C67—C68 | 0.0 (4) |
C18—C25—C28—S2 | 178.64 (18) | C67—N4—C66—C65 | 0.2 (4) |
C18—C25—C28—C29 | 0.3 (4) | C68—C64—C65—C66 | 0.6 (3) |
C19—C18—C25—C26 | 129.1 (2) | C69—C70—C71—C72 | −0.4 (4) |
C19—C18—C25—C28 | −47.8 (3) | C70—C69—C74—C73 | 0.1 (3) |
C19—C20—C21—C22 | −1.6 (4) | C70—C69—C75—O1 | −3.2 (3) |
C20—C19—C24—C23 | −1.8 (3) | C70—C69—C75—O2 | 178.7 (2) |
C20—C21—C22—C23 | −0.5 (4) | C70—C71—C72—O3 | 176.2 (2) |
C21—C22—C23—C24 | 1.5 (4) | C70—C71—C72—C73 | 0.5 (3) |
C22—C23—C24—C19 | −0.3 (4) | C71—C72—C73—C74 | −0.3 (3) |
C24—C19—C20—C21 | 2.8 (4) | C72—O3—C79—C78 | −50.6 (3) |
C25—C18—C19—C20 | −46.7 (3) | C72—O3—C79—C80 | 134.4 (2) |
C25—C18—C19—C24 | 132.4 (2) | C72—C73—C74—C69 | 0.0 (3) |
C25—C26—C27—S2 | 0.4 (3) | C74—C69—C70—C71 | 0.1 (3) |
C25—C26—C27—C30 | −179.6 (2) | C74—C69—C75—O1 | 175.74 (19) |
C26—C25—C28—S2 | 1.4 (3) | C74—C69—C75—O2 | −2.4 (3) |
C26—C25—C28—C29 | −176.9 (2) | C75—C69—C70—C71 | 179.1 (2) |
C26—C27—C30—C31 | −33.7 (4) | C75—C69—C74—C73 | −178.85 (19) |
C26—C27—C30—C34 | 143.9 (3) | C76—C77—C78—C79 | −0.6 (3) |
C27—S2—C28—C25 | −1.01 (19) | C77—C76—C81—C80 | −0.1 (3) |
C27—S2—C28—C29 | 177.6 (2) | C77—C76—C82—O4 | −3.7 (3) |
C27—C30—C31—C32 | 178.2 (2) | C77—C76—C82—O5 | 173.7 (2) |
C27—C30—C34—C33 | −178.9 (3) | C77—C78—C79—O3 | −174.90 (19) |
C28—S2—C27—C26 | 0.32 (19) | C77—C78—C79—C80 | −0.1 (3) |
C28—S2—C27—C30 | −179.6 (2) | C78—C79—C80—C81 | 0.7 (3) |
C28—C25—C26—C27 | −1.2 (3) | C79—O3—C72—C71 | 131.2 (2) |
C30—C31—C32—N2 | 0.8 (4) | C79—O3—C72—C73 | −53.0 (3) |
C31—C30—C34—C33 | −1.2 (4) | C79—C80—C81—C76 | −0.5 (3) |
C32—N2—C33—C34 | 0.6 (5) | C81—C76—C77—C78 | 0.7 (3) |
C33—N2—C32—C31 | −1.4 (4) | C81—C76—C82—O4 | 178.64 (19) |
C34—C30—C31—C32 | 0.5 (4) | C81—C76—C82—O5 | −3.9 (3) |
C35—C36—C37—C38 | −172.1 (2) | C82—C76—C77—C78 | −176.9 (2) |
C35—C36—C41—C40 | 171.53 (19) | C82—C76—C81—C80 | 177.5 (2) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
C78H56N4O9S4Zn2·3(C4H9NO)·5(H2O) | Z = 2 |
Mr = 1803.69 | F(000) = 1884 |
Triclinic, P1 | Dx = 1.360 Mg m−3 |
a = 11.873 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 17.012 (3) Å | Cell parameters from 6082 reflections |
c = 22.921 (4) Å | θ = 2.2–26.7° |
α = 78.006 (4)° | µ = 0.71 mm−1 |
β = 76.999 (4)° | T = 90 K |
γ = 83.799 (4)° | Prism, colourless |
V = 4403.4 (14) Å3 | 0.2 × 0.1 × 0.06 mm |
Bruker APEX-II CCD diffractometer | Rint = 0.092 |
φ and ω scans | θmax = 28.4°, θmin = 1.2° |
27985 measured reflections | h = −15→15 |
27985 independent reflections | k = −22→22 |
18444 reflections with I > 2σ(I) | l = 0→30 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.077 | H-atom parameters constrained |
wR(F2) = 0.214 | w = 1/[σ2(Fo2) + (0.0758P)2 + 13.018P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
27985 reflections | Δρmax = 1.02 e Å−3 |
1169 parameters | Δρmin = −1.21 e Å−3 |
66 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn01 | 0.25711 (5) | 0.74937 (3) | 0.60798 (3) | 0.01026 (13) | |
Zn02 | 0.74692 (5) | 0.24118 (3) | 0.61126 (3) | 0.01127 (13) | |
S1 | 1.09814 (11) | 0.26213 (8) | 0.83388 (6) | 0.0161 (3) | |
S2 | 0.76961 (11) | 0.58098 (8) | 0.84679 (6) | 0.0165 (3) | |
S3 | 0.26867 (11) | 0.07830 (7) | 0.85233 (6) | 0.0158 (3) | |
S4 | 0.59580 (11) | −0.23827 (8) | 0.83878 (6) | 0.0154 (3) | |
O1 | 0.6685 (3) | 0.3159 (2) | 0.55501 (17) | 0.0199 (8) | |
O2 | 0.5934 (4) | 0.3749 (2) | 0.63351 (18) | 0.0266 (9) | |
O3 | 0.3522 (3) | 0.6565 (2) | 0.58053 (16) | 0.0168 (8) | |
O4 | 0.5144 (3) | 0.7065 (2) | 0.52016 (19) | 0.0261 (9) | |
O5 | 0.8740 (3) | 0.1711 (2) | 0.57444 (16) | 0.0170 (8) | |
O6 | 0.7299 (3) | 0.1143 (2) | 0.55448 (16) | 0.0151 (7) | |
O7 | 0.8612 (3) | 0.19024 (19) | 0.43567 (16) | 0.0139 (7) | |
O8 | 0.9092 (3) | 0.1170 (2) | 0.36259 (16) | 0.0184 (8) | |
O9 | 0.3763 (3) | 0.8351 (2) | 0.54436 (16) | 0.0154 (7) | |
H9A | 0.441215 | 0.810236 | 0.531516 | 0.023* | |
H9B | 0.349835 | 0.853585 | 0.511845 | 0.023* | |
N1 | 0.8294 (4) | 0.2790 (2) | 0.67011 (19) | 0.0143 (9) | |
N2 | 1.1381 (4) | 0.6694 (2) | 0.67115 (19) | 0.0138 (9) | |
N3 | 0.6360 (4) | 0.1731 (2) | 0.67969 (19) | 0.0140 (9) | |
N4 | 0.3230 (4) | −0.2277 (2) | 0.67808 (19) | 0.0139 (9) | |
C1 | 0.9164 (4) | 0.3425 (3) | 0.9826 (2) | 0.0109 (9) | |
C2 | 0.9397 (4) | 0.2866 (3) | 1.0384 (2) | 0.0121 (10) | |
C3 | 0.9271 (4) | 0.2037 (3) | 1.0462 (2) | 0.0147 (10) | |
H3 | 0.898878 | 0.183746 | 1.016744 | 0.018* | |
C4 | 0.9554 (4) | 0.1503 (3) | 1.0965 (2) | 0.0168 (11) | |
H4 | 0.946550 | 0.094426 | 1.101024 | 0.020* | |
C5 | 0.9966 (4) | 0.1783 (3) | 1.1401 (2) | 0.0156 (10) | |
H5 | 1.015496 | 0.141941 | 1.174484 | 0.019* | |
C6 | 1.0097 (4) | 0.2602 (3) | 1.1326 (2) | 0.0176 (11) | |
H6 | 1.038296 | 0.279725 | 1.162101 | 0.021* | |
C7 | 0.9815 (4) | 0.3139 (3) | 1.0826 (2) | 0.0153 (10) | |
H7 | 0.990795 | 0.369719 | 1.078353 | 0.018* | |
C8 | 0.9633 (4) | 0.3153 (3) | 0.9238 (2) | 0.0118 (10) | |
C9 | 0.8986 (4) | 0.3234 (3) | 0.8772 (2) | 0.0114 (9) | |
H9 | 0.820446 | 0.344688 | 0.881516 | 0.014* | |
C10 | 0.9596 (4) | 0.2978 (3) | 0.8255 (2) | 0.0115 (9) | |
C11 | 1.0746 (4) | 0.2810 (3) | 0.9066 (2) | 0.0120 (9) | |
C12 | 1.1695 (4) | 0.2591 (3) | 0.9421 (2) | 0.0162 (10) | |
H12A | 1.158716 | 0.205574 | 0.967771 | 0.024* | |
H12B | 1.166891 | 0.298798 | 0.967972 | 0.024* | |
H12C | 1.244807 | 0.258779 | 0.913772 | 0.024* | |
C13 | 0.9182 (4) | 0.2944 (3) | 0.7709 (2) | 0.0134 (10) | |
C14 | 0.8092 (5) | 0.3272 (4) | 0.7628 (3) | 0.0248 (13) | |
H14 | 0.762518 | 0.356055 | 0.791825 | 0.030* | |
C15 | 0.7686 (5) | 0.3183 (4) | 0.7134 (3) | 0.0241 (12) | |
H15 | 0.693369 | 0.341062 | 0.709546 | 0.029* | |
C16 | 0.9364 (4) | 0.2490 (3) | 0.6762 (2) | 0.0155 (10) | |
H16 | 0.981931 | 0.222182 | 0.645548 | 0.019* | |
C17 | 0.9834 (5) | 0.2551 (3) | 0.7248 (2) | 0.0169 (11) | |
H17 | 1.059560 | 0.232912 | 0.727162 | 0.020* | |
C18 | 0.8548 (4) | 0.4149 (3) | 0.9848 (2) | 0.0116 (9) | |
C19 | 0.7905 (4) | 0.4381 (3) | 1.0432 (2) | 0.0127 (10) | |
C20 | 0.8035 (4) | 0.5124 (3) | 1.0561 (2) | 0.0154 (10) | |
H20 | 0.854739 | 0.548243 | 1.027677 | 0.019* | |
C21 | 0.7427 (5) | 0.5352 (3) | 1.1099 (2) | 0.0185 (11) | |
H21 | 0.754206 | 0.585707 | 1.118451 | 0.022* | |
C22 | 0.6649 (5) | 0.4843 (3) | 1.1513 (3) | 0.0230 (12) | |
H22 | 0.622793 | 0.499707 | 1.188028 | 0.028* | |
C23 | 0.6498 (5) | 0.4106 (3) | 1.1379 (3) | 0.0215 (12) | |
H23 | 0.596435 | 0.375530 | 1.165545 | 0.026* | |
C24 | 0.7118 (4) | 0.3878 (3) | 1.0847 (2) | 0.0163 (10) | |
H24 | 0.700719 | 0.337198 | 1.076252 | 0.020* | |
C25 | 0.8478 (4) | 0.4748 (3) | 0.9283 (2) | 0.0117 (10) | |
C26 | 0.9428 (4) | 0.4939 (3) | 0.8776 (2) | 0.0129 (10) | |
H26 | 1.018813 | 0.469480 | 0.877030 | 0.016* | |
C27 | 0.9150 (4) | 0.5498 (3) | 0.8306 (2) | 0.0134 (10) | |
C28 | 0.7474 (4) | 0.5200 (3) | 0.9178 (2) | 0.0137 (10) | |
C29 | 0.6274 (4) | 0.5220 (3) | 0.9571 (3) | 0.0192 (11) | |
H29A | 0.608862 | 0.467325 | 0.978380 | 0.029* | |
H29B | 0.571320 | 0.543850 | 0.931399 | 0.029* | |
H29C | 0.624003 | 0.556280 | 0.987025 | 0.029* | |
C30 | 0.9906 (4) | 0.5869 (3) | 0.7738 (2) | 0.0123 (10) | |
C31 | 1.1063 (5) | 0.5611 (3) | 0.7574 (3) | 0.0212 (12) | |
H31 | 1.137308 | 0.514646 | 0.781067 | 0.025* | |
C32 | 1.1760 (4) | 0.6033 (3) | 0.7066 (2) | 0.0186 (11) | |
H32 | 1.254939 | 0.584703 | 0.696205 | 0.022* | |
C33 | 1.0251 (4) | 0.6919 (3) | 0.6854 (2) | 0.0160 (10) | |
H33 | 0.995412 | 0.736954 | 0.659904 | 0.019* | |
C34 | 0.9502 (4) | 0.6530 (3) | 0.7350 (2) | 0.0156 (10) | |
H34 | 0.870743 | 0.671214 | 0.742950 | 0.019* | |
C35 | 0.3526 (4) | −0.0881 (3) | 0.9901 (2) | 0.0113 (9) | |
C36 | 0.2867 (4) | −0.0645 (3) | 1.0485 (2) | 0.0107 (9) | |
C37 | 0.2972 (4) | 0.0110 (3) | 1.0605 (2) | 0.0146 (10) | |
H37 | 0.348631 | 0.046826 | 1.032247 | 0.017* | |
C38 | 0.2327 (4) | 0.0346 (3) | 1.1138 (2) | 0.0162 (10) | |
H38 | 0.241701 | 0.085966 | 1.121766 | 0.019* | |
C39 | 0.1560 (4) | −0.0163 (3) | 1.1549 (2) | 0.0171 (11) | |
H39 | 0.111696 | −0.000068 | 1.190967 | 0.021* | |
C40 | 0.1446 (4) | −0.0915 (3) | 1.1428 (2) | 0.0177 (11) | |
H40 | 0.092078 | −0.126861 | 1.170749 | 0.021* | |
C41 | 0.2089 (4) | −0.1154 (3) | 1.0905 (2) | 0.0160 (10) | |
H41 | 0.200076 | −0.167020 | 1.082978 | 0.019* | |
C42 | 0.3459 (4) | −0.0279 (3) | 0.9338 (2) | 0.0112 (9) | |
C43 | 0.4417 (4) | −0.0082 (3) | 0.8841 (2) | 0.0120 (10) | |
H43 | 0.517732 | −0.032256 | 0.883999 | 0.014* | |
C44 | 0.4143 (4) | 0.0482 (3) | 0.8368 (2) | 0.0149 (10) | |
C45 | 0.2460 (4) | 0.0164 (3) | 0.9228 (2) | 0.0131 (10) | |
C46 | 0.1258 (4) | 0.0171 (3) | 0.9615 (2) | 0.0164 (11) | |
H46A | 0.120574 | 0.051548 | 0.991476 | 0.025* | |
H46B | 0.108441 | −0.037852 | 0.982729 | 0.025* | |
H46C | 0.069846 | 0.038005 | 0.935523 | 0.025* | |
C47 | 0.4900 (4) | 0.0874 (3) | 0.7810 (2) | 0.0140 (10) | |
C48 | 0.6075 (5) | 0.0653 (3) | 0.7666 (3) | 0.0224 (12) | |
H48 | 0.639917 | 0.020472 | 0.791122 | 0.027* | |
C49 | 0.6767 (5) | 0.1089 (3) | 0.7164 (3) | 0.0227 (12) | |
H49 | 0.756913 | 0.092934 | 0.707163 | 0.027* | |
C50 | 0.5223 (4) | 0.1935 (3) | 0.6929 (2) | 0.0178 (11) | |
H50 | 0.491775 | 0.238012 | 0.667199 | 0.021* | |
C51 | 0.4482 (4) | 0.1528 (3) | 0.7419 (2) | 0.0174 (11) | |
H51 | 0.367973 | 0.169108 | 0.749388 | 0.021* | |
C52 | 0.4134 (4) | −0.1606 (3) | 0.9887 (2) | 0.0118 (9) | |
C53 | 0.4364 (4) | −0.2174 (3) | 1.0442 (2) | 0.0127 (10) | |
C54 | 0.4200 (4) | −0.2993 (3) | 1.0519 (2) | 0.0149 (10) | |
H54 | 0.390987 | −0.318200 | 1.022340 | 0.018* | |
C55 | 0.4459 (5) | −0.3539 (3) | 1.1027 (3) | 0.0212 (12) | |
H55 | 0.433707 | −0.409397 | 1.107553 | 0.025* | |
C56 | 0.4891 (5) | −0.3269 (3) | 1.1456 (2) | 0.0199 (11) | |
H56 | 0.506571 | −0.363575 | 1.180262 | 0.024* | |
C57 | 0.5068 (5) | −0.2462 (3) | 1.1379 (2) | 0.0195 (11) | |
H57 | 0.537127 | −0.227716 | 1.167213 | 0.023* | |
C58 | 0.4810 (4) | −0.1917 (3) | 1.0879 (2) | 0.0152 (10) | |
H58 | 0.493785 | −0.136414 | 1.083295 | 0.018* | |
C59 | 0.4605 (4) | −0.1877 (3) | 0.9299 (2) | 0.0114 (9) | |
C60 | 0.3947 (4) | −0.1811 (3) | 0.8842 (2) | 0.0113 (9) | |
H60 | 0.315944 | −0.160981 | 0.889211 | 0.014* | |
C61 | 0.4555 (4) | −0.2064 (3) | 0.8319 (2) | 0.0133 (10) | |
C62 | 0.5725 (4) | −0.2203 (3) | 0.9121 (2) | 0.0125 (10) | |
C63 | 0.6680 (4) | −0.2398 (3) | 0.9462 (2) | 0.0177 (11) | |
H63A | 0.656742 | −0.291918 | 0.973924 | 0.027* | |
H63B | 0.667648 | −0.197904 | 0.969886 | 0.027* | |
H63C | 0.742385 | −0.242400 | 0.917394 | 0.027* | |
C64 | 0.4116 (4) | −0.2112 (3) | 0.7782 (2) | 0.0129 (10) | |
C65 | 0.2942 (5) | −0.1964 (3) | 0.7777 (2) | 0.0182 (11) | |
H65 | 0.242082 | −0.180371 | 0.811788 | 0.022* | |
C66 | 0.2536 (5) | −0.2050 (3) | 0.7276 (2) | 0.0194 (11) | |
H66 | 0.173209 | −0.194529 | 0.728160 | 0.023* | |
C67 | 0.4361 (4) | −0.2422 (3) | 0.6784 (2) | 0.0181 (11) | |
H67 | 0.486037 | −0.258564 | 0.643758 | 0.022* | |
C68 | 0.4838 (4) | −0.2345 (3) | 0.7265 (2) | 0.0171 (11) | |
H68 | 0.564699 | −0.244899 | 0.724501 | 0.021* | |
C69 | 0.5503 (4) | 0.4364 (3) | 0.5374 (2) | 0.0151 (10) | |
C70 | 0.5191 (4) | 0.5106 (3) | 0.5551 (2) | 0.0158 (10) | |
H70 | 0.531625 | 0.517879 | 0.593131 | 0.019* | |
C71 | 0.4701 (4) | 0.5742 (3) | 0.5183 (2) | 0.0132 (10) | |
C72 | 0.6064 (5) | 0.3715 (3) | 0.5793 (2) | 0.0168 (11) | |
C73 | 0.4432 (4) | 0.6529 (3) | 0.5400 (2) | 0.0141 (10) | |
C74 | 0.9228 (4) | 0.0607 (3) | 0.5225 (2) | 0.0137 (10) | |
C75 | 0.9534 (4) | 0.0618 (3) | 0.4599 (2) | 0.0118 (9) | |
C76 | 1.0300 (4) | 0.0010 (3) | 0.4379 (2) | 0.0152 (10) | |
H76 | 1.050194 | 0.001758 | 0.395303 | 0.018* | |
C77 | 0.8337 (5) | 0.1199 (3) | 0.5512 (2) | 0.0151 (10) | |
C78 | 0.9051 (4) | 0.1270 (3) | 0.4152 (2) | 0.0127 (10) | |
O10 | 0.8664 (4) | 0.5737 (3) | 0.5547 (3) | 0.0504 (14) | |
N5 | 1.0374 (6) | 0.5292 (3) | 0.5814 (3) | 0.0429 (15) | |
C79 | 0.9785 (7) | 0.5744 (4) | 0.5441 (3) | 0.0427 (18) | |
C80 | 1.0418 (6) | 0.6297 (4) | 0.4886 (3) | 0.0443 (18) | |
H80A | 0.987275 | 0.655038 | 0.462847 | 0.066* | |
H80B | 1.103554 | 0.598495 | 0.465439 | 0.066* | |
H80C | 1.075611 | 0.671499 | 0.501740 | 0.066* | |
C81 | 1.1643 (6) | 0.5281 (5) | 0.5700 (4) | 0.0483 (19) | |
H81A | 1.198153 | 0.498791 | 0.536929 | 0.072* | |
H81B | 1.190993 | 0.501306 | 0.607083 | 0.072* | |
H81C | 1.188481 | 0.583473 | 0.558311 | 0.072* | |
C82 | 0.9752 (9) | 0.4750 (5) | 0.6362 (4) | 0.069 (3) | |
H82A | 0.982762 | 0.492658 | 0.673067 | 0.103* | |
H82B | 1.008814 | 0.419686 | 0.636736 | 0.103* | |
H82C | 0.893065 | 0.476958 | 0.634669 | 0.103* | |
O11 | 0.2259 (4) | 0.1602 (3) | 0.6887 (2) | 0.0366 (11) | |
N6 | 0.3173 (5) | 0.0689 (3) | 0.6313 (3) | 0.0340 (13) | |
C83 | 0.2349 (6) | 0.0914 (4) | 0.6752 (3) | 0.0373 (16) | |
C84 | 0.1502 (6) | 0.0301 (4) | 0.7107 (4) | 0.048 (2) | |
H84A | 0.192265 | −0.017860 | 0.729290 | 0.073* | |
H84B | 0.107155 | 0.015251 | 0.683265 | 0.073* | |
H84C | 0.095935 | 0.053152 | 0.742801 | 0.073* | |
C85 | 0.3264 (8) | −0.0086 (5) | 0.6147 (4) | 0.068 (3) | |
H85A | 0.357553 | −0.048983 | 0.645172 | 0.103* | |
H85B | 0.378337 | −0.007043 | 0.574665 | 0.103* | |
H85C | 0.249583 | −0.022642 | 0.612785 | 0.103* | |
C86 | 0.3975 (6) | 0.1296 (5) | 0.5929 (3) | 0.051 (2) | |
H86A | 0.380040 | 0.180265 | 0.608026 | 0.076* | |
H86B | 0.387733 | 0.138693 | 0.550582 | 0.076* | |
H86C | 0.477506 | 0.109875 | 0.594624 | 0.076* | |
O13 | 1.2518 (4) | 0.3284 (3) | 0.5308 (3) | 0.0515 (14) | |
H13A | 1.314115 | 0.321181 | 0.505192 | 0.077* | |
H13B | 1.214679 | 0.371168 | 0.517013 | 0.077* | |
O14 | 0.3743 (7) | 0.4124 (5) | 0.7190 (4) | 0.085 (2) | |
H14A | 0.313343 | 0.404345 | 0.746690 | 0.128* | |
H14B | 0.359727 | 0.396627 | 0.688849 | 0.128* | |
O15 | 0.2670 (6) | 0.3244 (4) | 0.6539 (3) | 0.0600 (16) | |
H15A | 0.217302 | 0.364037 | 0.650036 | 0.090* | |
H15B | 0.293008 | 0.316378 | 0.617752 | 0.090* | |
O16 | 1.1291 (12) | 0.1699 (7) | 0.5600 (6) | 0.158 (4) | |
H16A | 1.161174 | 0.138521 | 0.535715 | 0.237* | |
H16B | 1.156798 | 0.215113 | 0.543252 | 0.237* | |
O17 | 0.8938 (4) | −0.0971 (3) | 0.7321 (2) | 0.0445 (13) | |
H17A | 0.956204 | −0.103800 | 0.706295 | 0.067* | |
H17B | 0.852229 | −0.134026 | 0.730429 | 0.067* | |
O12 | 0.7702 (10) | −0.1981 (7) | 0.6916 (5) | 0.033 (2) | 0.661 (13) |
N7 | 0.6978 (8) | −0.1130 (6) | 0.6178 (4) | 0.033 (2) | 0.661 (13) |
C87 | 0.7545 (11) | −0.1800 (9) | 0.6364 (7) | 0.035 (3) | 0.661 (13) |
C88 | 0.7961 (12) | −0.2383 (7) | 0.5951 (6) | 0.054 (4) | 0.661 (13) |
H88A | 0.823075 | −0.289213 | 0.618358 | 0.081* | 0.661 (13) |
H88B | 0.860150 | −0.216500 | 0.562687 | 0.081* | 0.661 (13) |
H88C | 0.732671 | −0.247856 | 0.577046 | 0.081* | 0.661 (13) |
C88A | 0.6468 (16) | −0.0594 (8) | 0.6622 (7) | 0.037 (3) | 0.661 (13) |
H88D | 0.660769 | −0.084913 | 0.702590 | 0.056* | 0.661 (13) |
H88E | 0.563249 | −0.050300 | 0.664123 | 0.056* | 0.661 (13) |
H88F | 0.682978 | −0.007753 | 0.648981 | 0.056* | 0.661 (13) |
C89 | 0.6723 (12) | −0.0869 (8) | 0.5569 (6) | 0.041 (3) | 0.661 (13) |
H89A | 0.726917 | −0.115304 | 0.528138 | 0.062* | 0.661 (13) |
H89B | 0.679918 | −0.028792 | 0.543912 | 0.062* | 0.661 (13) |
H89C | 0.593088 | −0.099259 | 0.557922 | 0.062* | 0.661 (13) |
O12A | 0.777 (2) | −0.2056 (15) | 0.6675 (11) | 0.038 (5) | 0.339 (13) |
N7A | 0.7692 (18) | −0.1509 (11) | 0.5736 (10) | 0.050 (5) | 0.339 (13) |
C87A | 0.742 (3) | −0.147 (2) | 0.6331 (16) | 0.050 (6) | 0.339 (13) |
C89A | 0.722 (3) | −0.0884 (17) | 0.5309 (15) | 0.059 (7) | 0.339 (13) |
H89D | 0.665887 | −0.111011 | 0.514398 | 0.089* | 0.339 (13) |
H89E | 0.784440 | −0.066751 | 0.497593 | 0.089* | 0.339 (13) |
H89F | 0.682777 | −0.045195 | 0.551943 | 0.089* | 0.339 (13) |
C90 | 0.659 (3) | −0.0804 (19) | 0.6522 (18) | 0.049 (7) | 0.339 (13) |
H90A | 0.581985 | −0.088340 | 0.646375 | 0.074* | 0.339 (13) |
H90B | 0.685235 | −0.028866 | 0.627501 | 0.074* | 0.339 (13) |
H90C | 0.655114 | −0.080212 | 0.695332 | 0.074* | 0.339 (13) |
C90A | 0.837 (2) | −0.2120 (14) | 0.5528 (13) | 0.047 (6) | 0.339 (13) |
H90D | 0.856215 | −0.251704 | 0.587398 | 0.071* | 0.339 (13) |
H90E | 0.908458 | −0.191331 | 0.526066 | 0.071* | 0.339 (13) |
H90F | 0.795833 | −0.237631 | 0.529961 | 0.071* | 0.339 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn01 | 0.0117 (3) | 0.0082 (3) | 0.0106 (3) | 0.0035 (2) | −0.0027 (2) | −0.0029 (2) |
Zn02 | 0.0133 (3) | 0.0084 (3) | 0.0119 (3) | 0.0037 (2) | −0.0031 (2) | −0.0030 (2) |
S1 | 0.0119 (6) | 0.0189 (6) | 0.0186 (6) | 0.0055 (5) | −0.0044 (5) | −0.0080 (5) |
S2 | 0.0107 (6) | 0.0159 (6) | 0.0191 (6) | 0.0032 (5) | −0.0020 (5) | 0.0018 (5) |
S3 | 0.0119 (6) | 0.0141 (6) | 0.0186 (6) | 0.0022 (5) | −0.0025 (5) | 0.0010 (5) |
S4 | 0.0127 (6) | 0.0183 (6) | 0.0162 (6) | 0.0043 (5) | −0.0040 (5) | −0.0072 (5) |
O1 | 0.024 (2) | 0.0150 (18) | 0.0195 (19) | 0.0104 (15) | −0.0082 (16) | −0.0034 (15) |
O2 | 0.039 (3) | 0.021 (2) | 0.021 (2) | 0.0127 (18) | −0.0162 (18) | −0.0036 (16) |
O3 | 0.0175 (19) | 0.0110 (17) | 0.0183 (19) | 0.0041 (14) | 0.0024 (15) | −0.0039 (14) |
O4 | 0.022 (2) | 0.0143 (18) | 0.038 (2) | −0.0012 (16) | 0.0032 (18) | −0.0082 (17) |
O5 | 0.0193 (19) | 0.0158 (18) | 0.0174 (18) | 0.0082 (15) | −0.0058 (15) | −0.0093 (14) |
O6 | 0.0138 (18) | 0.0134 (17) | 0.0170 (18) | 0.0033 (14) | −0.0034 (14) | −0.0020 (14) |
O7 | 0.0140 (18) | 0.0112 (16) | 0.0153 (17) | 0.0060 (14) | −0.0045 (14) | −0.0015 (13) |
O8 | 0.023 (2) | 0.0146 (17) | 0.0168 (19) | 0.0033 (15) | −0.0068 (15) | −0.0008 (14) |
O9 | 0.0145 (18) | 0.0145 (17) | 0.0155 (18) | 0.0013 (14) | −0.0016 (14) | −0.0019 (14) |
N1 | 0.013 (2) | 0.013 (2) | 0.016 (2) | 0.0021 (16) | −0.0021 (17) | −0.0056 (17) |
N2 | 0.013 (2) | 0.015 (2) | 0.012 (2) | 0.0006 (16) | −0.0012 (16) | −0.0011 (16) |
N3 | 0.016 (2) | 0.013 (2) | 0.012 (2) | 0.0018 (17) | −0.0027 (17) | −0.0015 (16) |
N4 | 0.017 (2) | 0.0106 (19) | 0.014 (2) | 0.0014 (16) | −0.0033 (17) | −0.0020 (16) |
C1 | 0.008 (2) | 0.010 (2) | 0.016 (2) | 0.0001 (18) | −0.0051 (18) | −0.0036 (18) |
C2 | 0.010 (2) | 0.010 (2) | 0.015 (2) | 0.0017 (18) | −0.0024 (19) | −0.0034 (18) |
C3 | 0.017 (3) | 0.010 (2) | 0.017 (3) | 0.0006 (19) | −0.005 (2) | −0.0040 (19) |
C4 | 0.019 (3) | 0.008 (2) | 0.021 (3) | 0.0048 (19) | −0.004 (2) | 0.0001 (19) |
C5 | 0.015 (3) | 0.015 (2) | 0.014 (2) | 0.005 (2) | −0.004 (2) | −0.0008 (19) |
C6 | 0.014 (3) | 0.021 (3) | 0.019 (3) | 0.003 (2) | −0.004 (2) | −0.007 (2) |
C7 | 0.013 (2) | 0.014 (2) | 0.019 (3) | 0.0018 (19) | −0.003 (2) | −0.005 (2) |
C8 | 0.014 (2) | 0.007 (2) | 0.014 (2) | −0.0018 (18) | −0.0027 (19) | −0.0012 (18) |
C9 | 0.011 (2) | 0.008 (2) | 0.016 (2) | −0.0006 (18) | −0.0051 (19) | −0.0024 (18) |
C10 | 0.009 (2) | 0.007 (2) | 0.019 (3) | 0.0017 (17) | −0.0056 (19) | −0.0031 (18) |
C11 | 0.012 (2) | 0.011 (2) | 0.016 (2) | 0.0019 (18) | −0.0060 (19) | −0.0052 (18) |
C12 | 0.015 (3) | 0.015 (2) | 0.021 (3) | 0.003 (2) | −0.009 (2) | −0.004 (2) |
C13 | 0.015 (2) | 0.009 (2) | 0.017 (2) | −0.0002 (19) | −0.005 (2) | −0.0041 (19) |
C14 | 0.017 (3) | 0.037 (3) | 0.026 (3) | 0.009 (2) | −0.007 (2) | −0.021 (3) |
C15 | 0.016 (3) | 0.032 (3) | 0.028 (3) | 0.012 (2) | −0.008 (2) | −0.018 (3) |
C16 | 0.016 (3) | 0.015 (2) | 0.016 (3) | 0.004 (2) | −0.001 (2) | −0.009 (2) |
C17 | 0.014 (3) | 0.018 (3) | 0.020 (3) | 0.002 (2) | −0.005 (2) | −0.007 (2) |
C18 | 0.011 (2) | 0.010 (2) | 0.015 (2) | −0.0042 (18) | −0.0026 (19) | −0.0030 (18) |
C19 | 0.010 (2) | 0.010 (2) | 0.016 (2) | 0.0030 (18) | −0.0033 (19) | −0.0006 (18) |
C20 | 0.015 (2) | 0.012 (2) | 0.018 (3) | 0.0003 (19) | −0.001 (2) | −0.0051 (19) |
C21 | 0.019 (3) | 0.014 (2) | 0.023 (3) | 0.003 (2) | −0.002 (2) | −0.009 (2) |
C22 | 0.026 (3) | 0.019 (3) | 0.019 (3) | 0.010 (2) | −0.002 (2) | −0.003 (2) |
C23 | 0.022 (3) | 0.016 (3) | 0.021 (3) | 0.000 (2) | 0.003 (2) | −0.001 (2) |
C24 | 0.017 (3) | 0.011 (2) | 0.019 (3) | −0.001 (2) | −0.003 (2) | −0.0009 (19) |
C25 | 0.010 (2) | 0.006 (2) | 0.019 (3) | −0.0034 (18) | −0.0019 (19) | −0.0031 (18) |
C26 | 0.011 (2) | 0.010 (2) | 0.020 (3) | −0.0005 (18) | −0.0032 (19) | −0.0056 (19) |
C27 | 0.010 (2) | 0.012 (2) | 0.018 (3) | −0.0015 (18) | −0.0026 (19) | −0.0012 (19) |
C28 | 0.013 (2) | 0.012 (2) | 0.014 (2) | −0.0004 (19) | 0.0003 (19) | −0.0017 (18) |
C29 | 0.012 (2) | 0.018 (3) | 0.025 (3) | 0.002 (2) | 0.000 (2) | −0.003 (2) |
C30 | 0.013 (2) | 0.010 (2) | 0.014 (2) | −0.0010 (18) | −0.0015 (19) | −0.0040 (18) |
C31 | 0.018 (3) | 0.018 (3) | 0.022 (3) | 0.002 (2) | −0.001 (2) | 0.006 (2) |
C32 | 0.009 (2) | 0.019 (3) | 0.024 (3) | 0.008 (2) | −0.004 (2) | 0.000 (2) |
C33 | 0.014 (2) | 0.013 (2) | 0.018 (3) | 0.003 (2) | −0.004 (2) | 0.0018 (19) |
C34 | 0.010 (2) | 0.014 (2) | 0.020 (3) | 0.0044 (19) | −0.002 (2) | 0.001 (2) |
C35 | 0.011 (2) | 0.011 (2) | 0.015 (2) | −0.0019 (18) | −0.0051 (19) | −0.0044 (18) |
C36 | 0.011 (2) | 0.007 (2) | 0.014 (2) | 0.0017 (17) | −0.0031 (18) | −0.0022 (17) |
C37 | 0.015 (2) | 0.012 (2) | 0.016 (2) | −0.0025 (19) | −0.003 (2) | −0.0028 (19) |
C38 | 0.020 (3) | 0.010 (2) | 0.020 (3) | 0.002 (2) | −0.002 (2) | −0.008 (2) |
C39 | 0.017 (3) | 0.015 (2) | 0.018 (3) | 0.004 (2) | −0.002 (2) | −0.005 (2) |
C40 | 0.017 (3) | 0.015 (2) | 0.018 (3) | −0.001 (2) | 0.003 (2) | −0.002 (2) |
C41 | 0.018 (3) | 0.010 (2) | 0.019 (3) | 0.000 (2) | −0.003 (2) | −0.0017 (19) |
C42 | 0.010 (2) | 0.009 (2) | 0.015 (2) | −0.0001 (18) | −0.0024 (18) | −0.0025 (18) |
C43 | 0.009 (2) | 0.009 (2) | 0.016 (2) | −0.0002 (18) | −0.0006 (19) | −0.0031 (18) |
C44 | 0.013 (2) | 0.012 (2) | 0.020 (3) | 0.0021 (19) | −0.002 (2) | −0.007 (2) |
C45 | 0.014 (2) | 0.011 (2) | 0.013 (2) | 0.0015 (19) | −0.0028 (19) | −0.0003 (18) |
C46 | 0.010 (2) | 0.017 (2) | 0.019 (3) | 0.001 (2) | 0.001 (2) | −0.002 (2) |
C47 | 0.019 (3) | 0.010 (2) | 0.013 (2) | −0.0002 (19) | −0.003 (2) | −0.0025 (18) |
C48 | 0.022 (3) | 0.012 (2) | 0.023 (3) | 0.006 (2) | 0.001 (2) | 0.008 (2) |
C49 | 0.014 (3) | 0.019 (3) | 0.026 (3) | 0.007 (2) | 0.003 (2) | 0.005 (2) |
C50 | 0.017 (3) | 0.014 (2) | 0.021 (3) | 0.000 (2) | −0.008 (2) | 0.003 (2) |
C51 | 0.011 (2) | 0.021 (3) | 0.020 (3) | 0.002 (2) | −0.005 (2) | −0.002 (2) |
C52 | 0.009 (2) | 0.013 (2) | 0.015 (2) | 0.0020 (18) | −0.0033 (18) | −0.0070 (19) |
C53 | 0.008 (2) | 0.011 (2) | 0.018 (2) | 0.0020 (18) | −0.0023 (19) | −0.0034 (19) |
C54 | 0.016 (3) | 0.011 (2) | 0.019 (3) | −0.0010 (19) | −0.006 (2) | −0.0034 (19) |
C55 | 0.026 (3) | 0.010 (2) | 0.025 (3) | 0.000 (2) | −0.002 (2) | −0.001 (2) |
C56 | 0.020 (3) | 0.019 (3) | 0.017 (3) | 0.004 (2) | −0.005 (2) | 0.003 (2) |
C57 | 0.021 (3) | 0.020 (3) | 0.021 (3) | 0.008 (2) | −0.011 (2) | −0.009 (2) |
C58 | 0.017 (3) | 0.011 (2) | 0.019 (3) | 0.0002 (19) | −0.005 (2) | −0.0041 (19) |
C59 | 0.013 (2) | 0.008 (2) | 0.014 (2) | −0.0007 (18) | −0.0033 (19) | −0.0035 (18) |
C60 | 0.011 (2) | 0.009 (2) | 0.014 (2) | −0.0022 (18) | −0.0020 (18) | −0.0016 (18) |
C61 | 0.014 (2) | 0.009 (2) | 0.019 (3) | 0.0036 (18) | −0.008 (2) | −0.0035 (19) |
C62 | 0.014 (2) | 0.011 (2) | 0.014 (2) | 0.0026 (19) | −0.0055 (19) | −0.0050 (18) |
C63 | 0.015 (3) | 0.017 (2) | 0.022 (3) | 0.000 (2) | −0.008 (2) | −0.004 (2) |
C64 | 0.016 (2) | 0.008 (2) | 0.015 (2) | 0.0012 (19) | −0.0044 (19) | −0.0033 (18) |
C65 | 0.016 (3) | 0.026 (3) | 0.014 (2) | 0.006 (2) | −0.004 (2) | −0.009 (2) |
C66 | 0.015 (3) | 0.025 (3) | 0.019 (3) | 0.009 (2) | −0.008 (2) | −0.006 (2) |
C67 | 0.014 (3) | 0.022 (3) | 0.016 (3) | 0.002 (2) | 0.000 (2) | −0.006 (2) |
C68 | 0.010 (2) | 0.024 (3) | 0.018 (3) | 0.002 (2) | −0.003 (2) | −0.008 (2) |
C69 | 0.014 (2) | 0.011 (2) | 0.019 (3) | 0.0025 (19) | −0.004 (2) | −0.0009 (19) |
C70 | 0.020 (3) | 0.014 (2) | 0.013 (2) | 0.003 (2) | −0.003 (2) | −0.0041 (19) |
C71 | 0.015 (2) | 0.009 (2) | 0.015 (2) | 0.0021 (18) | 0.0003 (19) | −0.0049 (18) |
C72 | 0.021 (3) | 0.008 (2) | 0.021 (3) | 0.004 (2) | −0.008 (2) | −0.001 (2) |
C73 | 0.015 (2) | 0.011 (2) | 0.015 (2) | 0.0031 (19) | −0.0030 (19) | −0.0020 (19) |
C74 | 0.014 (2) | 0.011 (2) | 0.019 (3) | 0.0047 (19) | −0.004 (2) | −0.0086 (19) |
C75 | 0.011 (2) | 0.011 (2) | 0.012 (2) | 0.0032 (18) | −0.0032 (18) | −0.0013 (18) |
C76 | 0.018 (3) | 0.014 (2) | 0.013 (2) | 0.004 (2) | −0.003 (2) | −0.0046 (19) |
C77 | 0.022 (3) | 0.010 (2) | 0.010 (2) | 0.008 (2) | −0.002 (2) | −0.0023 (18) |
C78 | 0.008 (2) | 0.015 (2) | 0.014 (2) | 0.0014 (18) | −0.0009 (18) | −0.0019 (19) |
O10 | 0.039 (3) | 0.045 (3) | 0.062 (4) | −0.010 (2) | −0.004 (3) | −0.001 (3) |
N5 | 0.052 (4) | 0.036 (3) | 0.044 (4) | −0.006 (3) | −0.014 (3) | −0.009 (3) |
C79 | 0.051 (5) | 0.029 (4) | 0.044 (4) | −0.005 (3) | 0.000 (4) | −0.007 (3) |
C80 | 0.039 (4) | 0.043 (4) | 0.042 (4) | −0.004 (3) | 0.001 (3) | 0.004 (3) |
C81 | 0.046 (5) | 0.046 (4) | 0.063 (5) | 0.004 (4) | −0.022 (4) | −0.024 (4) |
C82 | 0.122 (9) | 0.038 (4) | 0.043 (5) | −0.034 (5) | −0.016 (5) | 0.011 (4) |
O11 | 0.027 (2) | 0.030 (2) | 0.055 (3) | 0.0055 (19) | −0.007 (2) | −0.020 (2) |
N6 | 0.031 (3) | 0.034 (3) | 0.039 (3) | 0.002 (2) | −0.011 (2) | −0.010 (2) |
C83 | 0.025 (3) | 0.044 (4) | 0.043 (4) | 0.009 (3) | −0.009 (3) | −0.013 (3) |
C84 | 0.041 (4) | 0.049 (4) | 0.054 (5) | −0.022 (4) | 0.017 (4) | −0.025 (4) |
C85 | 0.068 (6) | 0.053 (5) | 0.086 (7) | −0.019 (4) | 0.023 (5) | −0.052 (5) |
C86 | 0.044 (4) | 0.079 (6) | 0.032 (4) | −0.033 (4) | 0.003 (3) | −0.016 (4) |
O13 | 0.031 (3) | 0.060 (4) | 0.051 (3) | 0.013 (2) | 0.005 (2) | −0.005 (3) |
O14 | 0.119 (7) | 0.074 (5) | 0.078 (5) | −0.004 (5) | −0.036 (5) | −0.034 (4) |
O15 | 0.075 (5) | 0.052 (4) | 0.057 (4) | −0.014 (3) | −0.009 (3) | −0.018 (3) |
O16 | 0.171 (11) | 0.129 (9) | 0.178 (12) | −0.003 (9) | −0.018 (9) | −0.063 (9) |
O17 | 0.035 (3) | 0.068 (4) | 0.031 (3) | 0.007 (3) | −0.001 (2) | −0.022 (3) |
O12 | 0.025 (4) | 0.034 (4) | 0.043 (5) | 0.009 (3) | −0.012 (4) | −0.012 (4) |
N7 | 0.030 (5) | 0.029 (4) | 0.043 (5) | −0.002 (3) | −0.011 (4) | −0.013 (3) |
C87 | 0.030 (6) | 0.029 (5) | 0.053 (6) | −0.002 (4) | −0.016 (4) | −0.012 (4) |
C88 | 0.072 (9) | 0.042 (6) | 0.057 (7) | 0.027 (6) | −0.038 (7) | −0.020 (5) |
C88A | 0.057 (8) | 0.020 (6) | 0.034 (6) | 0.007 (5) | −0.011 (5) | −0.005 (4) |
C89 | 0.038 (7) | 0.045 (6) | 0.044 (6) | 0.003 (6) | −0.012 (5) | −0.015 (5) |
O12A | 0.024 (8) | 0.042 (9) | 0.048 (10) | −0.001 (7) | −0.003 (9) | −0.014 (8) |
N7A | 0.057 (11) | 0.038 (8) | 0.065 (9) | −0.017 (7) | −0.025 (7) | −0.012 (6) |
C87A | 0.047 (13) | 0.043 (10) | 0.066 (9) | −0.004 (9) | −0.023 (8) | −0.012 (7) |
C89A | 0.076 (19) | 0.042 (10) | 0.072 (13) | −0.016 (11) | −0.036 (13) | −0.010 (10) |
C90 | 0.042 (12) | 0.041 (12) | 0.069 (16) | −0.009 (9) | −0.018 (11) | −0.011 (10) |
C90A | 0.055 (11) | 0.043 (9) | 0.061 (13) | −0.011 (8) | −0.037 (10) | −0.018 (9) |
Zn01—O3 | 1.968 (3) | C46—H46C | 0.9800 |
Zn01—O7i | 1.981 (3) | C47—C48 | 1.388 (7) |
Zn01—O9 | 2.211 (3) | C47—C51 | 1.397 (7) |
Zn01—N2ii | 2.150 (4) | C48—H48 | 0.9500 |
Zn01—N4iii | 2.059 (4) | C48—C49 | 1.379 (7) |
Zn02—O1 | 1.936 (4) | C49—H49 | 0.9500 |
Zn02—O5 | 1.967 (3) | C50—H50 | 0.9500 |
Zn02—N1 | 2.070 (4) | C50—C51 | 1.372 (7) |
Zn02—N3 | 2.045 (4) | C51—H51 | 0.9500 |
S1—C10 | 1.729 (5) | C52—C53 | 1.489 (7) |
S1—C11 | 1.719 (5) | C52—C59 | 1.485 (6) |
S2—C27 | 1.730 (5) | C53—C54 | 1.396 (7) |
S2—C28 | 1.721 (5) | C53—C58 | 1.393 (7) |
S3—C44 | 1.728 (5) | C54—H54 | 0.9500 |
S3—C45 | 1.717 (5) | C54—C55 | 1.400 (7) |
S4—C61 | 1.727 (5) | C55—H55 | 0.9500 |
S4—C62 | 1.726 (5) | C55—C56 | 1.383 (8) |
O1—C72 | 1.276 (6) | C56—H56 | 0.9500 |
O2—C72 | 1.231 (6) | C56—C57 | 1.379 (7) |
O3—C73 | 1.262 (6) | C57—H57 | 0.9500 |
O4—C73 | 1.255 (6) | C57—C58 | 1.387 (7) |
O5—C77 | 1.290 (6) | C58—H58 | 0.9500 |
O6—C77 | 1.230 (6) | C59—C60 | 1.422 (7) |
O7—C78 | 1.275 (6) | C59—C62 | 1.389 (7) |
O8—C78 | 1.243 (6) | C60—H60 | 0.9500 |
O9—H9A | 0.8595 | C60—C61 | 1.379 (7) |
O9—H9B | 0.8600 | C61—C64 | 1.461 (7) |
N1—C15 | 1.342 (7) | C62—C63 | 1.490 (7) |
N1—C16 | 1.343 (6) | C63—H63A | 0.9800 |
N2—C32 | 1.341 (6) | C63—H63B | 0.9800 |
N2—C33 | 1.341 (6) | C63—H63C | 0.9800 |
N3—C49 | 1.349 (6) | C64—C65 | 1.392 (7) |
N3—C50 | 1.339 (6) | C64—C68 | 1.400 (7) |
N4—C66 | 1.345 (7) | C65—H65 | 0.9500 |
N4—C67 | 1.340 (6) | C65—C66 | 1.381 (7) |
C1—C2 | 1.489 (7) | C66—H66 | 0.9500 |
C1—C8 | 1.484 (7) | C67—H67 | 0.9500 |
C1—C18 | 1.368 (6) | C67—C68 | 1.383 (7) |
C2—C3 | 1.404 (6) | C68—H68 | 0.9500 |
C2—C7 | 1.401 (7) | C69—C70 | 1.393 (7) |
C3—H3 | 0.9500 | C69—C71i | 1.400 (7) |
C3—C4 | 1.393 (7) | C69—C72 | 1.509 (7) |
C4—H4 | 0.9500 | C70—H70 | 0.9500 |
C4—C5 | 1.390 (7) | C70—C71 | 1.388 (7) |
C5—H5 | 0.9500 | C71—C73 | 1.502 (7) |
C5—C6 | 1.389 (7) | C74—C75 | 1.395 (7) |
C6—H6 | 0.9500 | C74—C76iv | 1.395 (7) |
C6—C7 | 1.390 (7) | C74—C77 | 1.518 (7) |
C7—H7 | 0.9500 | C75—C76 | 1.398 (7) |
C8—C9 | 1.428 (7) | C75—C78 | 1.504 (6) |
C8—C11 | 1.392 (7) | C76—H76 | 0.9500 |
C9—H9 | 0.9500 | O10—C79 | 1.300 (9) |
C9—C10 | 1.370 (7) | N5—C79 | 1.301 (9) |
C10—C13 | 1.458 (7) | N5—C81 | 1.469 (9) |
C11—C12 | 1.506 (7) | N5—C82 | 1.491 (9) |
C12—H12A | 0.9800 | C79—C80 | 1.514 (9) |
C12—H12B | 0.9800 | C80—H80A | 0.9800 |
C12—H12C | 0.9800 | C80—H80B | 0.9800 |
C13—C14 | 1.388 (7) | C80—H80C | 0.9800 |
C13—C17 | 1.405 (7) | C81—H81A | 0.9800 |
C14—H14 | 0.9500 | C81—H81B | 0.9800 |
C14—C15 | 1.368 (8) | C81—H81C | 0.9800 |
C15—H15 | 0.9500 | C82—H82A | 0.9800 |
C16—H16 | 0.9500 | C82—H82B | 0.9800 |
C16—C17 | 1.381 (7) | C82—H82C | 0.9800 |
C17—H17 | 0.9500 | O11—C83 | 1.260 (8) |
C18—C19 | 1.493 (7) | N6—C83 | 1.323 (8) |
C18—C25 | 1.483 (7) | N6—C85 | 1.433 (8) |
C19—C20 | 1.388 (7) | N6—C86 | 1.485 (8) |
C19—C24 | 1.394 (7) | C83—C84 | 1.506 (9) |
C20—H20 | 0.9500 | C84—H84A | 0.9800 |
C20—C21 | 1.389 (7) | C84—H84B | 0.9800 |
C21—H21 | 0.9500 | C84—H84C | 0.9800 |
C21—C22 | 1.394 (8) | C85—H85A | 0.9800 |
C22—H22 | 0.9500 | C85—H85B | 0.9800 |
C22—C23 | 1.390 (8) | C85—H85C | 0.9800 |
C23—H23 | 0.9500 | C86—H86A | 0.9800 |
C23—C24 | 1.382 (7) | C86—H86B | 0.9800 |
C24—H24 | 0.9500 | C86—H86C | 0.9800 |
C25—C26 | 1.437 (7) | O13—H13A | 0.8496 |
C25—C28 | 1.386 (7) | O13—H13B | 0.8491 |
C26—H26 | 0.9500 | O14—H14A | 0.8502 |
C26—C27 | 1.357 (7) | O14—H14B | 0.8491 |
C27—C30 | 1.467 (7) | O15—H15A | 0.8501 |
C28—C29 | 1.506 (7) | O15—H15B | 0.8502 |
C29—H29A | 0.9800 | O16—H16A | 0.8502 |
C29—H29B | 0.9800 | O16—H16B | 0.8496 |
C29—H29C | 0.9800 | O17—H17A | 0.8513 |
C30—C31 | 1.388 (7) | O17—H17B | 0.8506 |
C30—C34 | 1.395 (7) | O12—C87 | 1.290 (18) |
C31—H31 | 0.9500 | N7—C87 | 1.302 (16) |
C31—C32 | 1.380 (7) | N7—C88A | 1.491 (14) |
C32—H32 | 0.9500 | N7—C89 | 1.462 (16) |
C33—H33 | 0.9500 | C87—C88 | 1.482 (17) |
C33—C34 | 1.370 (7) | C88—H88A | 0.9800 |
C34—H34 | 0.9500 | C88—H88B | 0.9800 |
C35—C36 | 1.500 (6) | C88—H88C | 0.9800 |
C35—C42 | 1.483 (6) | C88A—H88D | 0.9800 |
C35—C52 | 1.363 (6) | C88A—H88E | 0.9800 |
C36—C37 | 1.392 (6) | C88A—H88F | 0.9800 |
C36—C41 | 1.399 (7) | C89—H89A | 0.9800 |
C37—H37 | 0.9500 | C89—H89B | 0.9800 |
C37—C38 | 1.398 (7) | C89—H89C | 0.9800 |
C38—H38 | 0.9500 | O12A—C87A | 1.23 (4) |
C38—C39 | 1.383 (7) | N7A—C87A | 1.34 (4) |
C39—H39 | 0.9500 | N7A—C89A | 1.45 (3) |
C39—C40 | 1.392 (7) | N7A—C90A | 1.34 (3) |
C40—H40 | 0.9500 | C87A—C90 | 1.49 (4) |
C40—C41 | 1.380 (7) | C89A—H89D | 0.9800 |
C41—H41 | 0.9500 | C89A—H89E | 0.9800 |
C42—C43 | 1.430 (6) | C89A—H89F | 0.9800 |
C42—C45 | 1.380 (7) | C90—H90A | 0.9800 |
C43—H43 | 0.9500 | C90—H90B | 0.9800 |
C43—C44 | 1.363 (7) | C90—H90C | 0.9800 |
C44—C47 | 1.465 (7) | C90A—H90D | 0.9800 |
C45—C46 | 1.502 (7) | C90A—H90E | 0.9800 |
C46—H46A | 0.9800 | C90A—H90F | 0.9800 |
C46—H46B | 0.9800 | ||
O3—Zn01—O7i | 122.17 (15) | N3—C49—H49 | 118.4 |
O3—Zn01—O9 | 91.79 (14) | C48—C49—H49 | 118.4 |
O3—Zn01—N2ii | 90.12 (15) | N3—C50—H50 | 118.7 |
O3—Zn01—N4iii | 105.91 (16) | N3—C50—C51 | 122.7 (5) |
O7i—Zn01—O9 | 84.34 (14) | C51—C50—H50 | 118.7 |
O7i—Zn01—N2ii | 94.85 (15) | C47—C51—H51 | 119.8 |
O7i—Zn01—N4iii | 131.47 (15) | C50—C51—C47 | 120.3 (5) |
N2ii—Zn01—O9 | 178.07 (14) | C50—C51—H51 | 119.8 |
N4iii—Zn01—O9 | 88.24 (15) | C35—C52—C53 | 123.5 (4) |
N4iii—Zn01—N2ii | 91.00 (16) | C35—C52—C59 | 120.6 (4) |
O1—Zn02—O5 | 116.01 (15) | C59—C52—C53 | 115.8 (4) |
O1—Zn02—N1 | 122.35 (16) | C54—C53—C52 | 120.3 (4) |
O1—Zn02—N3 | 113.14 (17) | C58—C53—C52 | 121.4 (4) |
O5—Zn02—N1 | 98.86 (15) | C58—C53—C54 | 118.2 (5) |
O5—Zn02—N3 | 109.61 (16) | C53—C54—H54 | 119.5 |
N3—Zn02—N1 | 94.10 (17) | C53—C54—C55 | 120.9 (5) |
C11—S1—C10 | 92.9 (2) | C55—C54—H54 | 119.5 |
C28—S2—C27 | 92.6 (2) | C54—C55—H55 | 120.1 |
C45—S3—C44 | 92.4 (2) | C56—C55—C54 | 119.8 (5) |
C62—S4—C61 | 92.9 (2) | C56—C55—H55 | 120.1 |
C72—O1—Zn02 | 113.0 (3) | C55—C56—H56 | 120.2 |
C73—O3—Zn01 | 131.1 (3) | C57—C56—C55 | 119.5 (5) |
C77—O5—Zn02 | 110.3 (3) | C57—C56—H56 | 120.2 |
C78—O7—Zn01i | 113.1 (3) | C56—C57—H57 | 119.5 |
Zn01—O9—H9A | 110.1 | C56—C57—C58 | 121.0 (5) |
Zn01—O9—H9B | 109.8 | C58—C57—H57 | 119.5 |
H9A—O9—H9B | 103.9 | C53—C58—H58 | 119.7 |
C15—N1—Zn02 | 120.3 (4) | C57—C58—C53 | 120.6 (5) |
C15—N1—C16 | 116.8 (5) | C57—C58—H58 | 119.7 |
C16—N1—Zn02 | 120.9 (3) | C60—C59—C52 | 122.7 (4) |
C32—N2—Zn01v | 121.3 (3) | C62—C59—C52 | 125.2 (4) |
C33—N2—Zn01v | 120.6 (3) | C62—C59—C60 | 112.0 (4) |
C33—N2—C32 | 116.8 (4) | C59—C60—H60 | 123.1 |
C49—N3—Zn02 | 120.7 (3) | C61—C60—C59 | 113.9 (4) |
C50—N3—Zn02 | 121.8 (3) | C61—C60—H60 | 123.1 |
C50—N3—C49 | 117.4 (4) | C60—C61—S4 | 110.3 (4) |
C66—N4—Zn01vi | 121.6 (4) | C60—C61—C64 | 127.4 (5) |
C67—N4—Zn01vi | 120.6 (3) | C64—C61—S4 | 122.2 (4) |
C67—N4—C66 | 117.5 (4) | C59—C62—S4 | 110.9 (4) |
C8—C1—C2 | 116.3 (4) | C59—C62—C63 | 129.7 (5) |
C18—C1—C2 | 122.3 (4) | C63—C62—S4 | 119.4 (4) |
C18—C1—C8 | 121.3 (4) | C62—C63—H63A | 109.5 |
C3—C2—C1 | 120.4 (4) | C62—C63—H63B | 109.5 |
C7—C2—C1 | 121.3 (4) | C62—C63—H63C | 109.5 |
C7—C2—C3 | 118.1 (4) | H63A—C63—H63B | 109.5 |
C2—C3—H3 | 119.6 | H63A—C63—H63C | 109.5 |
C4—C3—C2 | 120.8 (5) | H63B—C63—H63C | 109.5 |
C4—C3—H3 | 119.6 | C65—C64—C61 | 120.8 (4) |
C3—C4—H4 | 119.7 | C65—C64—C68 | 117.2 (5) |
C5—C4—C3 | 120.5 (5) | C68—C64—C61 | 122.0 (5) |
C5—C4—H4 | 119.7 | C64—C65—H65 | 120.0 |
C4—C5—H5 | 120.4 | C66—C65—C64 | 119.9 (5) |
C6—C5—C4 | 119.1 (5) | C66—C65—H65 | 120.0 |
C6—C5—H5 | 120.4 | N4—C66—C65 | 122.8 (5) |
C5—C6—H6 | 119.6 | N4—C66—H66 | 118.6 |
C5—C6—C7 | 120.8 (5) | C65—C66—H66 | 118.6 |
C7—C6—H6 | 119.6 | N4—C67—H67 | 118.4 |
C2—C7—H7 | 119.7 | N4—C67—C68 | 123.3 (5) |
C6—C7—C2 | 120.7 (5) | C68—C67—H67 | 118.4 |
C6—C7—H7 | 119.7 | C64—C68—H68 | 120.4 |
C9—C8—C1 | 123.1 (4) | C67—C68—C64 | 119.3 (5) |
C11—C8—C1 | 125.1 (4) | C67—C68—H68 | 120.4 |
C11—C8—C9 | 111.8 (4) | C70—C69—C71i | 119.1 (4) |
C8—C9—H9 | 123.1 | C70—C69—C72 | 117.7 (5) |
C10—C9—C8 | 113.8 (4) | C71i—C69—C72 | 123.2 (4) |
C10—C9—H9 | 123.1 | C69—C70—H70 | 119.4 |
C9—C10—S1 | 110.5 (4) | C71—C70—C69 | 121.1 (5) |
C9—C10—C13 | 127.8 (4) | C71—C70—H70 | 119.4 |
C13—C10—S1 | 121.6 (4) | C69i—C71—C73 | 122.8 (4) |
C8—C11—S1 | 111.0 (4) | C70—C71—C69i | 119.8 (4) |
C8—C11—C12 | 129.6 (5) | C70—C71—C73 | 117.5 (5) |
C12—C11—S1 | 119.4 (4) | O1—C72—C69 | 116.5 (5) |
C11—C12—H12A | 109.5 | O2—C72—O1 | 123.5 (5) |
C11—C12—H12B | 109.5 | O2—C72—C69 | 120.0 (5) |
C11—C12—H12C | 109.5 | O3—C73—C71 | 115.2 (4) |
H12A—C12—H12B | 109.5 | O4—C73—O3 | 125.7 (5) |
H12A—C12—H12C | 109.5 | O4—C73—C71 | 118.9 (4) |
H12B—C12—H12C | 109.5 | C75—C74—C77 | 123.8 (4) |
C14—C13—C10 | 121.5 (5) | C76iv—C74—C75 | 119.2 (4) |
C14—C13—C17 | 116.2 (5) | C76iv—C74—C77 | 116.9 (4) |
C17—C13—C10 | 122.3 (5) | C74—C75—C76 | 119.7 (4) |
C13—C14—H14 | 119.7 | C74—C75—C78 | 121.2 (4) |
C15—C14—C13 | 120.6 (5) | C76—C75—C78 | 119.1 (4) |
C15—C14—H14 | 119.7 | C74iv—C76—C75 | 121.2 (5) |
N1—C15—C14 | 123.4 (5) | C74iv—C76—H76 | 119.4 |
N1—C15—H15 | 118.3 | C75—C76—H76 | 119.4 |
C14—C15—H15 | 118.3 | O5—C77—C74 | 115.7 (4) |
N1—C16—H16 | 118.4 | O6—C77—O5 | 124.1 (4) |
N1—C16—C17 | 123.2 (5) | O6—C77—C74 | 120.1 (5) |
C17—C16—H16 | 118.4 | O7—C78—C75 | 115.4 (4) |
C13—C17—H17 | 120.1 | O8—C78—O7 | 124.6 (4) |
C16—C17—C13 | 119.7 (5) | O8—C78—C75 | 120.0 (4) |
C16—C17—H17 | 120.1 | C79—N5—C81 | 121.8 (7) |
C1—C18—C19 | 122.5 (4) | C79—N5—C82 | 119.3 (7) |
C1—C18—C25 | 121.2 (4) | C81—N5—C82 | 118.9 (7) |
C25—C18—C19 | 116.3 (4) | O10—C79—N5 | 120.7 (7) |
C20—C19—C18 | 120.5 (4) | O10—C79—C80 | 120.1 (7) |
C20—C19—C24 | 118.4 (5) | N5—C79—C80 | 119.2 (7) |
C24—C19—C18 | 121.1 (4) | C79—C80—H80A | 109.5 |
C19—C20—H20 | 119.5 | C79—C80—H80B | 109.5 |
C19—C20—C21 | 121.0 (5) | C79—C80—H80C | 109.5 |
C21—C20—H20 | 119.5 | H80A—C80—H80B | 109.5 |
C20—C21—H21 | 119.9 | H80A—C80—H80C | 109.5 |
C20—C21—C22 | 120.2 (5) | H80B—C80—H80C | 109.5 |
C22—C21—H21 | 119.9 | N5—C81—H81A | 109.5 |
C21—C22—H22 | 120.5 | N5—C81—H81B | 109.5 |
C23—C22—C21 | 118.9 (5) | N5—C81—H81C | 109.5 |
C23—C22—H22 | 120.5 | H81A—C81—H81B | 109.5 |
C22—C23—H23 | 119.7 | H81A—C81—H81C | 109.5 |
C24—C23—C22 | 120.5 (5) | H81B—C81—H81C | 109.5 |
C24—C23—H23 | 119.7 | N5—C82—H82A | 109.5 |
C19—C24—H24 | 119.5 | N5—C82—H82B | 109.5 |
C23—C24—C19 | 121.0 (5) | N5—C82—H82C | 109.5 |
C23—C24—H24 | 119.5 | H82A—C82—H82B | 109.5 |
C26—C25—C18 | 125.0 (4) | H82A—C82—H82C | 109.5 |
C28—C25—C18 | 124.0 (4) | H82B—C82—H82C | 109.5 |
C28—C25—C26 | 111.0 (4) | C83—N6—C85 | 123.5 (6) |
C25—C26—H26 | 122.8 | C83—N6—C86 | 118.5 (6) |
C27—C26—C25 | 114.3 (4) | C85—N6—C86 | 117.7 (6) |
C27—C26—H26 | 122.8 | O11—C83—N6 | 123.2 (7) |
C26—C27—S2 | 110.5 (4) | O11—C83—C84 | 119.4 (6) |
C26—C27—C30 | 129.1 (5) | N6—C83—C84 | 117.3 (6) |
C30—C27—S2 | 120.2 (4) | C83—C84—H84A | 109.5 |
C25—C28—S2 | 111.5 (4) | C83—C84—H84B | 109.5 |
C25—C28—C29 | 130.8 (5) | C83—C84—H84C | 109.5 |
C29—C28—S2 | 117.7 (4) | H84A—C84—H84B | 109.5 |
C28—C29—H29A | 109.5 | H84A—C84—H84C | 109.5 |
C28—C29—H29B | 109.5 | H84B—C84—H84C | 109.5 |
C28—C29—H29C | 109.5 | N6—C85—H85A | 109.5 |
H29A—C29—H29B | 109.5 | N6—C85—H85B | 109.5 |
H29A—C29—H29C | 109.5 | N6—C85—H85C | 109.5 |
H29B—C29—H29C | 109.5 | H85A—C85—H85B | 109.5 |
C31—C30—C27 | 122.2 (4) | H85A—C85—H85C | 109.5 |
C31—C30—C34 | 116.7 (4) | H85B—C85—H85C | 109.5 |
C34—C30—C27 | 121.0 (4) | N6—C86—H86A | 109.5 |
C30—C31—H31 | 120.2 | N6—C86—H86B | 109.5 |
C32—C31—C30 | 119.6 (5) | N6—C86—H86C | 109.5 |
C32—C31—H31 | 120.2 | H86A—C86—H86B | 109.5 |
N2—C32—C31 | 123.4 (5) | H86A—C86—H86C | 109.5 |
N2—C32—H32 | 118.3 | H86B—C86—H86C | 109.5 |
C31—C32—H32 | 118.3 | H13A—O13—H13B | 109.5 |
N2—C33—H33 | 118.4 | H14A—O14—H14B | 104.5 |
N2—C33—C34 | 123.3 (5) | H15A—O15—H15B | 104.4 |
C34—C33—H33 | 118.4 | H16A—O16—H16B | 104.5 |
C30—C34—H34 | 119.9 | H17A—O17—H17B | 104.3 |
C33—C34—C30 | 120.1 (5) | C87—N7—C88A | 118.8 (11) |
C33—C34—H34 | 119.9 | C87—N7—C89 | 125.5 (11) |
C42—C35—C36 | 115.7 (4) | C89—N7—C88A | 115.6 (10) |
C52—C35—C36 | 122.2 (4) | O12—C87—N7 | 120.6 (12) |
C52—C35—C42 | 122.1 (4) | O12—C87—C88 | 119.3 (13) |
C37—C36—C35 | 120.3 (4) | N7—C87—C88 | 120.1 (13) |
C37—C36—C41 | 118.3 (5) | C87—C88—H88A | 109.5 |
C41—C36—C35 | 121.3 (4) | C87—C88—H88B | 109.5 |
C36—C37—H37 | 119.7 | C87—C88—H88C | 109.5 |
C36—C37—C38 | 120.7 (5) | H88A—C88—H88B | 109.5 |
C38—C37—H37 | 119.7 | H88A—C88—H88C | 109.5 |
C37—C38—H38 | 119.8 | H88B—C88—H88C | 109.5 |
C39—C38—C37 | 120.4 (5) | N7—C88A—H88D | 109.5 |
C39—C38—H38 | 119.8 | N7—C88A—H88E | 109.5 |
C38—C39—H39 | 120.5 | N7—C88A—H88F | 109.5 |
C38—C39—C40 | 119.0 (5) | H88D—C88A—H88E | 109.5 |
C40—C39—H39 | 120.5 | H88D—C88A—H88F | 109.5 |
C39—C40—H40 | 119.6 | H88E—C88A—H88F | 109.5 |
C41—C40—C39 | 120.7 (5) | N7—C89—H89A | 109.5 |
C41—C40—H40 | 119.6 | N7—C89—H89B | 109.5 |
C36—C41—H41 | 119.6 | N7—C89—H89C | 109.5 |
C40—C41—C36 | 120.8 (5) | H89A—C89—H89B | 109.5 |
C40—C41—H41 | 119.6 | H89A—C89—H89C | 109.5 |
C43—C42—C35 | 124.6 (4) | H89B—C89—H89C | 109.5 |
C45—C42—C35 | 124.1 (4) | C87A—N7A—C89A | 119 (3) |
C45—C42—C43 | 111.2 (4) | C87A—N7A—C90A | 122 (3) |
C42—C43—H43 | 122.9 | C90A—N7A—C89A | 119 (2) |
C44—C43—C42 | 114.1 (4) | O12A—C87A—N7A | 116 (3) |
C44—C43—H43 | 122.9 | O12A—C87A—C90 | 126 (3) |
C43—C44—S3 | 110.4 (4) | N7A—C87A—C90 | 118 (3) |
C43—C44—C47 | 129.6 (5) | N7A—C89A—H89D | 109.5 |
C47—C44—S3 | 119.8 (4) | N7A—C89A—H89E | 109.5 |
C42—C45—S3 | 111.7 (4) | N7A—C89A—H89F | 109.5 |
C42—C45—C46 | 130.4 (4) | H89D—C89A—H89E | 109.5 |
C46—C45—S3 | 117.9 (4) | H89D—C89A—H89F | 109.5 |
C45—C46—H46A | 109.5 | H89E—C89A—H89F | 109.5 |
C45—C46—H46B | 109.5 | C87A—C90—H90A | 109.5 |
C45—C46—H46C | 109.5 | C87A—C90—H90B | 109.5 |
H46A—C46—H46B | 109.5 | C87A—C90—H90C | 109.5 |
H46A—C46—H46C | 109.5 | H90A—C90—H90B | 109.5 |
H46B—C46—H46C | 109.5 | H90A—C90—H90C | 109.5 |
C48—C47—C44 | 121.9 (4) | H90B—C90—H90C | 109.5 |
C48—C47—C51 | 116.9 (5) | N7A—C90A—H90D | 109.5 |
C51—C47—C44 | 121.0 (5) | N7A—C90A—H90E | 109.5 |
C47—C48—H48 | 120.2 | N7A—C90A—H90F | 109.5 |
C49—C48—C47 | 119.5 (5) | H90D—C90A—H90E | 109.5 |
C49—C48—H48 | 120.2 | H90D—C90A—H90F | 109.5 |
N3—C49—C48 | 123.2 (5) | H90E—C90A—H90F | 109.5 |
Zn01—O3—C73—O4 | 23.4 (8) | C35—C52—C59—C60 | −45.3 (7) |
Zn01—O3—C73—C71 | −161.3 (3) | C35—C52—C59—C62 | 133.1 (5) |
Zn01i—O7—C78—O8 | 24.9 (6) | C36—C35—C42—C43 | 138.4 (5) |
Zn01i—O7—C78—C75 | −154.8 (3) | C36—C35—C42—C45 | −41.4 (7) |
Zn01v—N2—C32—C31 | 163.7 (4) | C36—C35—C52—C53 | −10.2 (7) |
Zn01v—N2—C33—C34 | −164.0 (4) | C36—C35—C52—C59 | 169.4 (4) |
Zn01vi—N4—C66—C65 | 173.9 (4) | C36—C37—C38—C39 | −1.1 (8) |
Zn01vi—N4—C67—C68 | −174.4 (4) | C37—C36—C41—C40 | −0.4 (8) |
Zn02—O1—C72—O2 | −3.3 (7) | C37—C38—C39—C40 | 0.5 (8) |
Zn02—O1—C72—C69 | 174.9 (3) | C38—C39—C40—C41 | 0.1 (8) |
Zn02—O5—C77—O6 | −2.9 (6) | C39—C40—C41—C36 | −0.1 (8) |
Zn02—O5—C77—C74 | −178.7 (3) | C41—C36—C37—C38 | 1.0 (7) |
Zn02—N1—C15—C14 | 162.9 (5) | C42—C35—C36—C37 | −47.9 (6) |
Zn02—N1—C16—C17 | −162.5 (4) | C42—C35—C36—C41 | 128.5 (5) |
Zn02—N3—C49—C48 | 173.8 (5) | C42—C35—C52—C53 | 170.8 (4) |
Zn02—N3—C50—C51 | −174.0 (4) | C42—C35—C52—C59 | −9.6 (7) |
S1—C10—C13—C14 | −176.3 (4) | C42—C43—C44—S3 | −0.2 (5) |
S1—C10—C13—C17 | 6.5 (7) | C42—C43—C44—C47 | 174.8 (5) |
S2—C27—C30—C31 | −176.7 (4) | C43—C42—C45—S3 | 1.8 (5) |
S2—C27—C30—C34 | 6.7 (7) | C43—C42—C45—C46 | −179.3 (5) |
S3—C44—C47—C48 | 180.0 (4) | C43—C44—C47—C48 | 5.3 (9) |
S3—C44—C47—C51 | 4.5 (7) | C43—C44—C47—C51 | −170.2 (5) |
S4—C61—C64—C65 | 170.4 (4) | C44—S3—C45—C42 | −1.6 (4) |
S4—C61—C64—C68 | −6.4 (7) | C44—S3—C45—C46 | 179.3 (4) |
N1—C16—C17—C13 | 0.0 (8) | C44—C47—C48—C49 | −174.2 (5) |
N2—C33—C34—C30 | 0.4 (8) | C44—C47—C51—C50 | 174.0 (5) |
N3—C50—C51—C47 | 0.5 (9) | C45—S3—C44—C43 | 1.1 (4) |
N4—C67—C68—C64 | 0.6 (8) | C45—S3—C44—C47 | −174.6 (4) |
C1—C2—C3—C4 | 176.1 (5) | C45—C42—C43—C44 | −1.0 (6) |
C1—C2—C7—C6 | −176.0 (5) | C47—C48—C49—N3 | 0.0 (10) |
C1—C8—C9—C10 | 177.3 (4) | C48—C47—C51—C50 | −1.7 (8) |
C1—C8—C11—S1 | −177.1 (4) | C49—N3—C50—C51 | 1.0 (8) |
C1—C8—C11—C12 | 3.6 (8) | C50—N3—C49—C48 | −1.2 (9) |
C1—C18—C19—C20 | 131.0 (5) | C51—C47—C48—C49 | 1.5 (8) |
C1—C18—C19—C24 | −52.3 (7) | C52—C35—C36—C37 | 133.0 (5) |
C1—C18—C25—C26 | −41.3 (7) | C52—C35—C36—C41 | −50.5 (7) |
C1—C18—C25—C28 | 138.7 (5) | C52—C35—C42—C43 | −42.5 (7) |
C2—C1—C8—C9 | 136.3 (5) | C52—C35—C42—C45 | 137.6 (5) |
C2—C1—C8—C11 | −45.2 (6) | C52—C53—C54—C55 | 177.3 (5) |
C2—C1—C18—C19 | −9.9 (7) | C52—C53—C58—C57 | −177.0 (5) |
C2—C1—C18—C25 | 170.6 (4) | C52—C59—C60—C61 | 177.4 (4) |
C2—C3—C4—C5 | 0.1 (8) | C52—C59—C62—S4 | −176.3 (4) |
C3—C2—C7—C6 | 0.0 (7) | C52—C59—C62—C63 | 3.5 (8) |
C3—C4—C5—C6 | −0.4 (8) | C53—C52—C59—C60 | 134.4 (5) |
C4—C5—C6—C7 | 0.4 (8) | C53—C52—C59—C62 | −47.2 (7) |
C5—C6—C7—C2 | −0.3 (8) | C53—C54—C55—C56 | −0.6 (8) |
C7—C2—C3—C4 | 0.0 (7) | C54—C53—C58—C57 | −0.8 (7) |
C8—C1—C2—C3 | −43.6 (6) | C54—C55—C56—C57 | −0.3 (8) |
C8—C1—C2—C7 | 132.3 (5) | C55—C56—C57—C58 | 0.5 (8) |
C8—C1—C18—C19 | 169.8 (4) | C56—C57—C58—C53 | 0.0 (8) |
C8—C1—C18—C25 | −9.7 (7) | C58—C53—C54—C55 | 1.1 (7) |
C8—C9—C10—S1 | 0.6 (5) | C59—C52—C53—C54 | −45.4 (6) |
C8—C9—C10—C13 | 177.0 (4) | C59—C52—C53—C58 | 130.6 (5) |
C9—C8—C11—S1 | 1.5 (5) | C59—C60—C61—S4 | −0.4 (5) |
C9—C8—C11—C12 | −177.8 (5) | C59—C60—C61—C64 | 176.6 (4) |
C9—C10—C13—C14 | 7.6 (8) | C60—C59—C62—S4 | 2.3 (5) |
C9—C10—C13—C17 | −169.6 (5) | C60—C59—C62—C63 | −177.9 (5) |
C10—S1—C11—C8 | −1.1 (4) | C60—C61—C64—C65 | −6.3 (8) |
C10—S1—C11—C12 | 178.3 (4) | C60—C61—C64—C68 | 176.9 (5) |
C10—C13—C14—C15 | −175.2 (5) | C61—S4—C62—C59 | −2.1 (4) |
C10—C13—C17—C16 | 175.4 (5) | C61—S4—C62—C63 | 178.0 (4) |
C11—S1—C10—C9 | 0.3 (4) | C61—C64—C65—C66 | −176.9 (5) |
C11—S1—C10—C13 | −176.4 (4) | C61—C64—C68—C67 | 176.5 (5) |
C11—C8—C9—C10 | −1.4 (6) | C62—S4—C61—C60 | 1.4 (4) |
C13—C14—C15—N1 | −0.6 (10) | C62—S4—C61—C64 | −175.8 (4) |
C14—C13—C17—C16 | −1.9 (7) | C62—C59—C60—C61 | −1.2 (6) |
C15—N1—C16—C17 | 1.6 (7) | C64—C65—C66—N4 | 0.1 (8) |
C16—N1—C15—C14 | −1.4 (8) | C65—C64—C68—C67 | −0.5 (7) |
C17—C13—C14—C15 | 2.2 (8) | C66—N4—C67—C68 | −0.4 (8) |
C18—C1—C2—C3 | 136.1 (5) | C67—N4—C66—C65 | 0.0 (8) |
C18—C1—C2—C7 | −48.0 (7) | C68—C64—C65—C66 | 0.1 (7) |
C18—C1—C8—C9 | −43.4 (7) | C69—C70—C71—C69i | 1.0 (8) |
C18—C1—C8—C11 | 135.1 (5) | C69—C70—C71—C73 | −177.8 (5) |
C18—C19—C20—C21 | 178.9 (5) | C69i—C71—C73—O3 | 102.8 (6) |
C18—C19—C24—C23 | −178.0 (5) | C69i—C71—C73—O4 | −81.6 (7) |
C18—C25—C26—C27 | 178.9 (4) | C70—C69—C72—O1 | −157.0 (5) |
C18—C25—C28—S2 | −178.1 (4) | C70—C69—C72—O2 | 21.3 (8) |
C18—C25—C28—C29 | 0.6 (8) | C70—C71—C73—O3 | −78.4 (6) |
C19—C18—C25—C26 | 139.1 (5) | C70—C71—C73—O4 | 97.1 (6) |
C19—C18—C25—C28 | −40.9 (7) | C71i—C69—C70—C71 | −1.0 (8) |
C19—C20—C21—C22 | −1.7 (8) | C71i—C69—C72—O1 | 22.1 (7) |
C20—C19—C24—C23 | −1.2 (8) | C71i—C69—C72—O2 | −159.6 (5) |
C20—C21—C22—C23 | 0.3 (8) | C72—C69—C70—C71 | 178.2 (5) |
C21—C22—C23—C24 | 0.6 (8) | C74—C75—C76—C74iv | −0.4 (8) |
C22—C23—C24—C19 | −0.2 (8) | C74—C75—C78—O7 | 17.7 (7) |
C24—C19—C20—C21 | 2.1 (8) | C74—C75—C78—O8 | −162.0 (5) |
C25—C18—C19—C20 | −49.5 (6) | C75—C74—C77—O5 | −110.5 (6) |
C25—C18—C19—C24 | 127.2 (5) | C75—C74—C77—O6 | 73.6 (7) |
C25—C26—C27—S2 | −0.3 (5) | C76iv—C74—C75—C76 | 0.4 (8) |
C25—C26—C27—C30 | 175.9 (5) | C76iv—C74—C75—C78 | −179.9 (5) |
C26—C25—C28—S2 | 2.0 (5) | C76iv—C74—C77—O5 | 73.8 (6) |
C26—C25—C28—C29 | −179.4 (5) | C76iv—C74—C77—O6 | −102.1 (6) |
C26—C27—C30—C31 | 7.4 (8) | C76—C75—C78—O7 | −162.6 (4) |
C26—C27—C30—C34 | −169.2 (5) | C76—C75—C78—O8 | 17.7 (7) |
C27—S2—C28—C25 | −1.8 (4) | C77—C74—C75—C76 | −175.2 (5) |
C27—S2—C28—C29 | 179.3 (4) | C77—C74—C75—C78 | 4.5 (8) |
C27—C30—C31—C32 | −173.5 (5) | C78—C75—C76—C74iv | 179.9 (5) |
C27—C30—C34—C33 | 173.4 (5) | C81—N5—C79—O10 | 179.2 (6) |
C28—S2—C27—C26 | 1.2 (4) | C81—N5—C79—C80 | −2.3 (10) |
C28—S2—C27—C30 | −175.4 (4) | C82—N5—C79—O10 | 1.2 (11) |
C28—C25—C26—C27 | −1.1 (6) | C82—N5—C79—C80 | 179.7 (7) |
C30—C31—C32—N2 | 0.0 (9) | C85—N6—C83—O11 | −178.5 (7) |
C31—C30—C34—C33 | −3.4 (8) | C85—N6—C83—C84 | 2.6 (11) |
C32—N2—C33—C34 | 2.9 (8) | C86—N6—C83—O11 | −5.0 (10) |
C33—N2—C32—C31 | −3.0 (8) | C86—N6—C83—C84 | 176.2 (6) |
C34—C30—C31—C32 | 3.2 (8) | C88A—N7—C87—O12 | −2.6 (18) |
C35—C36—C37—C38 | 177.6 (5) | C88A—N7—C87—C88 | 173.9 (13) |
C35—C36—C41—C40 | −176.9 (5) | C89—N7—C87—O12 | −178.5 (12) |
C35—C42—C43—C44 | 179.1 (4) | C89—N7—C87—C88 | −2.0 (19) |
C35—C42—C45—S3 | −178.3 (4) | C89A—N7A—C87A—O12A | 174 (3) |
C35—C42—C45—C46 | 0.6 (8) | C89A—N7A—C87A—C90 | 3 (4) |
C35—C52—C53—C54 | 134.2 (5) | C90A—N7A—C87A—O12A | −4 (4) |
C35—C52—C53—C58 | −49.7 (7) | C90A—N7A—C87A—C90 | −175 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) x, y+1, z; (iv) −x+2, −y, −z+1; (v) x+1, y, z; (vi) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9A···O4 | 0.86 | 1.92 | 2.665 (5) | 144 |
O9—H9B···O6i | 0.86 | 1.92 | 2.776 (5) | 171 |
O13—H13A···O4vii | 0.85 | 2.02 | 2.810 (6) | 154 |
O13—H13B···O10vii | 0.85 | 2.09 | 2.821 (8) | 143 |
O14—H14B···O15 | 0.85 | 2.11 | 2.879 (9) | 150 |
O15—H15B···O13ii | 0.85 | 2.12 | 2.854 (8) | 144 |
O17—H17A···O8iv | 0.85 | 2.01 | 2.854 (6) | 173 |
O17—H17B···O12 | 0.85 | 1.99 | 2.790 (13) | 157 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iv) −x+2, −y, −z+1; (vii) −x+2, −y+1, −z+1. |
C43H30N2O6S2Zn·C3H7NO·H2O | Z = 2 |
Mr = 891.29 | F(000) = 924 |
Triclinic, P1 | Dx = 1.413 Mg m−3 |
a = 10.1309 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.6998 (4) Å | Cell parameters from 6014 reflections |
c = 19.7642 (7) Å | θ = 2.2–25.6° |
α = 76.491 (1)° | µ = 0.74 mm−1 |
β = 78.625 (1)° | T = 90 K |
γ = 67.929 (1)° | Prism, colourless |
V = 2095.28 (13) Å3 | 0.04 × 0.02 × 0.01 mm |
Bruker APEX-II CCD diffractometer | Rint = 0.073 |
φ and ω scans | θmax = 28.3°, θmin = 1.9° |
10384 measured reflections | h = −13→13 |
10384 independent reflections | k = −15→15 |
8202 reflections with I > 2σ(I) | l = 0→26 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.034P)2 + 4.5742P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
10384 reflections | Δρmax = 0.82 e Å−3 |
554 parameters | Δρmin = −0.78 e Å−3 |
1 restraint |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.91508 (5) | 0.60731 (4) | 0.42781 (2) | 0.01248 (10) | |
S1 | 1.28832 (11) | 0.18979 (10) | 0.17108 (5) | 0.0182 (2) | |
S2 | 0.65420 (10) | 0.20324 (10) | 0.18077 (5) | 0.0171 (2) | |
O1 | 0.7247 (3) | 0.6368 (3) | 0.48040 (15) | 0.0187 (6) | |
O2 | 0.6307 (3) | 0.7043 (3) | 0.37861 (15) | 0.0236 (7) | |
O3 | 0.5591 (3) | 0.8664 (3) | 0.52967 (16) | 0.0244 (7) | |
O4 | 0.5236 (3) | 0.7644 (3) | 0.63958 (15) | 0.0226 (6) | |
O5 | 0.1946 (3) | 0.6033 (3) | 0.39303 (14) | 0.0179 (6) | |
O6 | 0.0417 (3) | 0.6098 (3) | 0.49053 (14) | 0.0148 (6) | |
N1 | 0.9781 (3) | 0.4932 (3) | 0.35535 (16) | 0.0134 (7) | |
N2 | 0.8948 (3) | −0.2239 (3) | 0.35669 (18) | 0.0166 (7) | |
C1 | 1.0686 (4) | 0.2512 (3) | 0.00962 (19) | 0.0128 (8) | |
C2 | 1.1662 (4) | 0.2679 (4) | −0.0566 (2) | 0.0154 (8) | |
C3 | 1.2318 (4) | 0.3562 (4) | −0.0682 (2) | 0.0166 (8) | |
H3A | 1.212646 | 0.407782 | −0.034286 | 0.020* | |
C4 | 1.3250 (4) | 0.3710 (4) | −0.1284 (2) | 0.0206 (9) | |
H4 | 1.369604 | 0.431877 | −0.135113 | 0.025* | |
C5 | 1.3535 (4) | 0.2971 (4) | −0.1790 (2) | 0.0230 (9) | |
H5 | 1.415895 | 0.308132 | −0.220737 | 0.028* | |
C6 | 1.2893 (5) | 0.2066 (4) | −0.1676 (2) | 0.0237 (10) | |
H6 | 1.309796 | 0.154240 | −0.201243 | 0.028* | |
C7 | 1.1956 (4) | 0.1926 (4) | −0.1073 (2) | 0.0195 (9) | |
H7 | 1.151165 | 0.131607 | −0.100292 | 0.023* | |
C8 | 1.1255 (4) | 0.2447 (4) | 0.0751 (2) | 0.0146 (8) | |
C9 | 1.0432 (4) | 0.3144 (4) | 0.1292 (2) | 0.0145 (8) | |
H9 | 0.946612 | 0.369137 | 0.126938 | 0.017* | |
C10 | 1.1159 (4) | 0.2951 (4) | 0.1844 (2) | 0.0149 (8) | |
C11 | 1.2618 (4) | 0.1729 (4) | 0.0910 (2) | 0.0167 (8) | |
C12 | 1.3834 (4) | 0.0887 (4) | 0.0494 (2) | 0.0231 (10) | |
H12A | 1.434 (2) | 0.1362 (14) | 0.0176 (14) | 0.035* | |
H12B | 1.3472 (11) | 0.050 (2) | 0.0243 (14) | 0.035* | |
H12C | 1.446 (3) | 0.027 (2) | 0.0799 (9) | 0.035* | |
C13 | 1.0682 (4) | 0.3569 (4) | 0.2460 (2) | 0.0134 (8) | |
C14 | 0.9320 (4) | 0.4474 (4) | 0.2530 (2) | 0.0213 (9) | |
H14 | 0.867233 | 0.463703 | 0.220211 | 0.026* | |
C15 | 0.8911 (4) | 0.5137 (4) | 0.3076 (2) | 0.0184 (9) | |
H15 | 0.798217 | 0.575713 | 0.311315 | 0.022* | |
C16 | 1.1073 (4) | 0.4023 (4) | 0.35080 (19) | 0.0136 (8) | |
H16 | 1.167751 | 0.384932 | 0.385774 | 0.016* | |
C17 | 1.1560 (4) | 0.3329 (4) | 0.2974 (2) | 0.0149 (8) | |
H17 | 1.248263 | 0.269620 | 0.295767 | 0.018* | |
C18 | 0.9373 (4) | 0.2443 (3) | 0.0119 (2) | 0.0144 (8) | |
C19 | 0.8640 (4) | 0.2691 (4) | −0.0517 (2) | 0.0134 (8) | |
C20 | 0.7944 (4) | 0.1898 (4) | −0.0569 (2) | 0.0163 (8) | |
H20 | 0.801801 | 0.116721 | −0.022370 | 0.020* | |
C21 | 0.7141 (4) | 0.2154 (4) | −0.1118 (2) | 0.0199 (9) | |
H21 | 0.667582 | 0.160071 | −0.114721 | 0.024* | |
C22 | 0.7025 (4) | 0.3227 (4) | −0.1622 (2) | 0.0195 (9) | |
H22 | 0.646979 | 0.341552 | −0.199453 | 0.023* | |
C23 | 0.7716 (4) | 0.4017 (4) | −0.1579 (2) | 0.0190 (9) | |
H23 | 0.764104 | 0.474698 | −0.192592 | 0.023* | |
C24 | 0.8528 (4) | 0.3754 (4) | −0.1030 (2) | 0.0150 (8) | |
H24 | 0.900490 | 0.430280 | −0.100753 | 0.018* | |
C25 | 0.8543 (4) | 0.2102 (4) | 0.0792 (2) | 0.0123 (7) | |
C26 | 0.9141 (4) | 0.1029 (4) | 0.1299 (2) | 0.0130 (8) | |
H26 | 1.010833 | 0.048030 | 0.123924 | 0.016* | |
C27 | 0.8207 (4) | 0.0860 (4) | 0.18738 (19) | 0.0128 (8) | |
C28 | 0.7112 (4) | 0.2727 (4) | 0.0989 (2) | 0.0149 (8) | |
C29 | 0.6052 (4) | 0.3853 (4) | 0.0605 (2) | 0.0208 (9) | |
H29A | 0.565 (3) | 0.3592 (8) | 0.0294 (14) | 0.031* | |
H29B | 0.6528 (15) | 0.441 (2) | 0.0341 (14) | 0.031* | |
H29C | 0.530 (3) | 0.427 (2) | 0.0936 (9) | 0.031* | |
C30 | 0.8455 (4) | −0.0174 (4) | 0.2469 (2) | 0.0134 (8) | |
C31 | 0.9611 (4) | −0.1288 (4) | 0.2409 (2) | 0.0151 (8) | |
H31 | 1.025535 | −0.135925 | 0.198795 | 0.018* | |
C32 | 0.9816 (4) | −0.2275 (4) | 0.2957 (2) | 0.0155 (8) | |
H32 | 1.060919 | −0.302205 | 0.290382 | 0.019* | |
C33 | 0.7834 (4) | −0.1168 (4) | 0.3636 (2) | 0.0175 (8) | |
H33 | 0.721668 | −0.112394 | 0.406559 | 0.021* | |
C34 | 0.7552 (4) | −0.0130 (4) | 0.3106 (2) | 0.0171 (8) | |
H34 | 0.675319 | 0.060606 | 0.317387 | 0.021* | |
C35 | 0.4746 (4) | 0.6892 (4) | 0.4842 (2) | 0.0170 (8) | |
C36 | 0.4256 (4) | 0.7348 (4) | 0.5472 (2) | 0.0168 (8) | |
C37 | 0.2907 (4) | 0.7380 (4) | 0.5814 (2) | 0.0201 (8) | |
H37 | 0.258107 | 0.766740 | 0.624992 | 0.024* | |
C38 | 0.2033 (4) | 0.7000 (4) | 0.5527 (2) | 0.0170 (8) | |
H38 | 0.110457 | 0.704500 | 0.575948 | 0.020* | |
C39 | 0.2520 (4) | 0.6549 (4) | 0.4897 (2) | 0.0158 (8) | |
C40 | 0.3883 (4) | 0.6489 (4) | 0.4559 (2) | 0.0160 (8) | |
H40 | 0.422207 | 0.617124 | 0.413267 | 0.019* | |
C41 | 0.6208 (4) | 0.6772 (4) | 0.4434 (2) | 0.0174 (8) | |
C42 | 0.5102 (4) | 0.7876 (4) | 0.5770 (2) | 0.0171 (8) | |
C43 | 0.1593 (4) | 0.6185 (3) | 0.4546 (2) | 0.0127 (8) | |
O7 | 1.2713 (3) | 0.0597 (3) | 0.4261 (2) | 0.0351 (8) | |
N3 | 1.2434 (4) | −0.0463 (4) | 0.3508 (2) | 0.0306 (9) | |
C44 | 1.3215 (5) | −0.0147 (4) | 0.3847 (3) | 0.0271 (10) | |
H44 | 1.422953 | −0.051785 | 0.376586 | 0.033* | |
C45 | 1.0879 (6) | 0.0064 (6) | 0.3606 (4) | 0.0558 (18) | |
H45A | 1.057220 | 0.068159 | 0.391738 | 0.084* | |
H45B | 1.048768 | −0.060603 | 0.381631 | 0.084* | |
H45C | 1.052657 | 0.047228 | 0.315176 | 0.084* | |
H3 | 0.598 (7) | 0.902 (6) | 0.548 (3) | 0.067* | |
C46 | 1.3096 (6) | −0.1357 (5) | 0.3030 (3) | 0.0358 (12) | |
H46A | 1.287441 | −0.093884 | 0.255416 | 0.054* | |
H46B | 1.272159 | −0.204883 | 0.317874 | 0.054* | |
H46C | 1.413840 | −0.168652 | 0.303579 | 0.054* | |
O8 | 0.4422 (4) | 0.4991 (3) | 0.29737 (18) | 0.0370 (9) | |
H8A | 0.475749 | 0.418366 | 0.310998 | 0.056* | |
H8B | 0.373187 | 0.526055 | 0.330089 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0112 (2) | 0.0154 (2) | 0.0109 (2) | −0.00300 (17) | −0.00305 (18) | −0.00368 (19) |
S1 | 0.0127 (5) | 0.0226 (5) | 0.0166 (5) | 0.0012 (4) | −0.0050 (4) | −0.0081 (4) |
S2 | 0.0128 (5) | 0.0179 (5) | 0.0153 (5) | −0.0016 (4) | −0.0012 (4) | 0.0001 (4) |
O1 | 0.0130 (14) | 0.0161 (14) | 0.0256 (15) | −0.0043 (11) | −0.0064 (12) | 0.0009 (12) |
O2 | 0.0187 (15) | 0.0317 (18) | 0.0216 (16) | −0.0074 (13) | −0.0023 (12) | −0.0095 (13) |
O3 | 0.0277 (17) | 0.0216 (16) | 0.0307 (17) | −0.0131 (13) | −0.0122 (14) | −0.0025 (13) |
O4 | 0.0175 (15) | 0.0278 (16) | 0.0248 (16) | −0.0068 (13) | −0.0023 (12) | −0.0108 (13) |
O5 | 0.0169 (14) | 0.0196 (15) | 0.0175 (14) | −0.0063 (12) | −0.0034 (12) | −0.0027 (12) |
O6 | 0.0125 (13) | 0.0177 (14) | 0.0153 (13) | −0.0073 (11) | −0.0035 (11) | −0.0001 (11) |
N1 | 0.0152 (16) | 0.0136 (16) | 0.0109 (15) | −0.0045 (13) | −0.0008 (13) | −0.0026 (13) |
N2 | 0.0119 (16) | 0.0185 (18) | 0.0172 (17) | −0.0019 (13) | −0.0020 (13) | −0.0044 (14) |
C1 | 0.0159 (18) | 0.0108 (19) | 0.0118 (18) | −0.0020 (15) | −0.0055 (15) | −0.0032 (14) |
C2 | 0.0113 (18) | 0.017 (2) | 0.0145 (19) | −0.0011 (15) | −0.0035 (15) | −0.0014 (16) |
C3 | 0.0121 (18) | 0.021 (2) | 0.0152 (19) | −0.0036 (16) | −0.0036 (15) | −0.0032 (16) |
C4 | 0.0128 (19) | 0.023 (2) | 0.024 (2) | −0.0069 (17) | −0.0018 (16) | −0.0013 (18) |
C5 | 0.0113 (19) | 0.037 (3) | 0.017 (2) | −0.0046 (18) | −0.0008 (16) | −0.0043 (19) |
C6 | 0.020 (2) | 0.035 (3) | 0.017 (2) | −0.0046 (19) | −0.0008 (17) | −0.0140 (19) |
C7 | 0.0132 (19) | 0.024 (2) | 0.023 (2) | −0.0042 (17) | −0.0032 (16) | −0.0096 (18) |
C8 | 0.0147 (19) | 0.015 (2) | 0.0144 (19) | −0.0040 (16) | −0.0032 (15) | −0.0039 (15) |
C9 | 0.0103 (18) | 0.017 (2) | 0.0161 (19) | −0.0051 (15) | −0.0009 (15) | −0.0038 (16) |
C10 | 0.0084 (17) | 0.016 (2) | 0.020 (2) | −0.0020 (15) | −0.0022 (15) | −0.0058 (16) |
C11 | 0.0152 (19) | 0.020 (2) | 0.0150 (19) | −0.0033 (16) | −0.0030 (15) | −0.0060 (16) |
C12 | 0.015 (2) | 0.026 (2) | 0.026 (2) | 0.0013 (18) | −0.0042 (17) | −0.0109 (19) |
C13 | 0.0140 (18) | 0.0133 (19) | 0.0141 (19) | −0.0061 (15) | −0.0030 (15) | −0.0015 (15) |
C14 | 0.015 (2) | 0.026 (2) | 0.018 (2) | 0.0016 (17) | −0.0053 (16) | −0.0066 (17) |
C15 | 0.0133 (19) | 0.025 (2) | 0.0148 (19) | −0.0005 (17) | −0.0045 (15) | −0.0077 (17) |
C16 | 0.0141 (18) | 0.0156 (19) | 0.0115 (18) | −0.0057 (15) | −0.0033 (15) | −0.0008 (15) |
C17 | 0.0112 (18) | 0.016 (2) | 0.0148 (19) | −0.0014 (16) | −0.0029 (15) | −0.0009 (15) |
C18 | 0.0177 (19) | 0.0119 (19) | 0.0129 (18) | −0.0028 (15) | −0.0059 (15) | −0.0014 (15) |
C19 | 0.0119 (18) | 0.0150 (19) | 0.0112 (18) | −0.0016 (15) | −0.0016 (14) | −0.0035 (15) |
C20 | 0.0132 (18) | 0.020 (2) | 0.0147 (19) | −0.0059 (16) | −0.0015 (15) | −0.0013 (16) |
C21 | 0.016 (2) | 0.028 (2) | 0.020 (2) | −0.0088 (18) | −0.0063 (17) | −0.0076 (18) |
C22 | 0.0130 (19) | 0.032 (2) | 0.0119 (19) | −0.0043 (17) | −0.0049 (15) | −0.0052 (17) |
C23 | 0.016 (2) | 0.023 (2) | 0.0116 (19) | −0.0013 (17) | −0.0006 (15) | −0.0002 (16) |
C24 | 0.0146 (18) | 0.018 (2) | 0.0141 (19) | −0.0072 (16) | −0.0019 (15) | −0.0027 (16) |
C25 | 0.0123 (18) | 0.0138 (19) | 0.0123 (18) | −0.0050 (15) | −0.0026 (14) | −0.0030 (15) |
C26 | 0.0106 (18) | 0.0126 (19) | 0.0157 (19) | −0.0017 (15) | −0.0034 (15) | −0.0046 (15) |
C27 | 0.0120 (17) | 0.0148 (19) | 0.0106 (18) | −0.0023 (15) | −0.0035 (14) | −0.0026 (15) |
C28 | 0.0151 (19) | 0.0149 (19) | 0.0122 (18) | −0.0041 (15) | −0.0005 (15) | −0.0002 (15) |
C29 | 0.018 (2) | 0.019 (2) | 0.019 (2) | −0.0015 (17) | −0.0018 (17) | −0.0012 (17) |
C30 | 0.0090 (17) | 0.017 (2) | 0.0152 (19) | −0.0053 (15) | −0.0025 (15) | −0.0028 (16) |
C31 | 0.0116 (18) | 0.019 (2) | 0.0138 (19) | −0.0038 (15) | −0.0006 (15) | −0.0038 (15) |
C32 | 0.0147 (19) | 0.016 (2) | 0.0143 (19) | −0.0016 (16) | −0.0039 (15) | −0.0043 (15) |
C33 | 0.019 (2) | 0.018 (2) | 0.0131 (19) | −0.0023 (16) | −0.0013 (16) | −0.0071 (16) |
C34 | 0.017 (2) | 0.015 (2) | 0.018 (2) | −0.0028 (16) | −0.0009 (16) | −0.0052 (16) |
C35 | 0.0103 (18) | 0.0100 (18) | 0.028 (2) | −0.0008 (15) | −0.0018 (16) | −0.0037 (16) |
C36 | 0.0146 (19) | 0.0126 (19) | 0.023 (2) | −0.0036 (15) | −0.0060 (16) | −0.0022 (16) |
C37 | 0.0195 (19) | 0.024 (2) | 0.019 (2) | −0.0077 (17) | −0.0022 (17) | −0.0081 (18) |
C38 | 0.0098 (18) | 0.021 (2) | 0.020 (2) | −0.0058 (16) | −0.0019 (15) | −0.0034 (16) |
C39 | 0.0149 (19) | 0.0133 (19) | 0.019 (2) | −0.0056 (15) | −0.0040 (16) | −0.0006 (15) |
C40 | 0.0134 (18) | 0.0126 (18) | 0.021 (2) | −0.0026 (15) | −0.0025 (16) | −0.0041 (16) |
C41 | 0.0127 (18) | 0.016 (2) | 0.026 (2) | −0.0054 (15) | −0.0009 (16) | −0.0089 (16) |
C42 | 0.0112 (17) | 0.0137 (19) | 0.025 (2) | 0.0001 (15) | −0.0041 (17) | −0.0066 (17) |
C43 | 0.0091 (17) | 0.0113 (18) | 0.0159 (19) | −0.0005 (14) | −0.0032 (14) | −0.0025 (15) |
O7 | 0.0315 (18) | 0.0311 (18) | 0.050 (2) | −0.0143 (15) | −0.0079 (17) | −0.0127 (18) |
N3 | 0.026 (2) | 0.023 (2) | 0.045 (2) | −0.0067 (17) | −0.0123 (19) | −0.0076 (18) |
C44 | 0.023 (2) | 0.020 (2) | 0.040 (3) | −0.0114 (19) | −0.007 (2) | 0.000 (2) |
C45 | 0.024 (3) | 0.049 (4) | 0.107 (6) | −0.008 (3) | −0.014 (3) | −0.042 (4) |
C46 | 0.038 (3) | 0.031 (3) | 0.039 (3) | −0.010 (2) | −0.010 (2) | −0.008 (2) |
O8 | 0.035 (2) | 0.035 (2) | 0.0250 (18) | 0.0004 (16) | 0.0019 (15) | 0.0008 (15) |
Zn1—O1 | 1.949 (3) | C19—C24 | 1.393 (5) |
Zn1—O6i | 1.964 (3) | C20—H20 | 0.9500 |
Zn1—N1 | 2.033 (3) | C20—C21 | 1.393 (5) |
Zn1—N2ii | 2.105 (3) | C21—H21 | 0.9500 |
S1—C10 | 1.729 (4) | C21—C22 | 1.390 (6) |
S1—C11 | 1.723 (4) | C22—H22 | 0.9500 |
S2—C27 | 1.734 (4) | C22—C23 | 1.378 (6) |
S2—C28 | 1.726 (4) | C23—H23 | 0.9500 |
O1—C41 | 1.278 (5) | C23—C24 | 1.397 (5) |
O2—C41 | 1.239 (5) | C24—H24 | 0.9500 |
O3—C42 | 1.314 (5) | C25—C26 | 1.424 (5) |
O3—H3 | 0.85 (2) | C25—C28 | 1.380 (5) |
O4—C42 | 1.225 (5) | C26—H26 | 0.9500 |
O5—C43 | 1.234 (4) | C26—C27 | 1.356 (5) |
O6—C43 | 1.287 (5) | C27—C30 | 1.461 (5) |
N1—C15 | 1.337 (5) | C28—C29 | 1.502 (5) |
N1—C16 | 1.344 (5) | C29—H29A | 0.96 (3) |
N2—C32 | 1.343 (5) | C29—H29B | 0.96 (3) |
N2—C33 | 1.348 (5) | C29—H29C | 0.96 (3) |
C1—C2 | 1.497 (5) | C30—C31 | 1.398 (5) |
C1—C8 | 1.493 (5) | C30—C34 | 1.402 (5) |
C1—C18 | 1.354 (5) | C31—H31 | 0.9500 |
C2—C3 | 1.381 (6) | C31—C32 | 1.370 (5) |
C2—C7 | 1.401 (6) | C32—H32 | 0.9500 |
C3—H3A | 0.9500 | C33—H33 | 0.9500 |
C3—C4 | 1.386 (6) | C33—C34 | 1.383 (6) |
C4—H4 | 0.9500 | C34—H34 | 0.9500 |
C4—C5 | 1.390 (6) | C35—C36 | 1.396 (6) |
C5—H5 | 0.9500 | C35—C40 | 1.388 (5) |
C5—C6 | 1.394 (6) | C35—C41 | 1.513 (5) |
C6—H6 | 0.9500 | C36—C37 | 1.392 (6) |
C6—C7 | 1.389 (6) | C36—C42 | 1.494 (5) |
C7—H7 | 0.9500 | C37—H37 | 0.9500 |
C8—C9 | 1.431 (5) | C37—C38 | 1.384 (5) |
C8—C11 | 1.373 (5) | C38—H38 | 0.9500 |
C9—H9 | 0.9500 | C38—C39 | 1.393 (6) |
C9—C10 | 1.363 (5) | C39—C40 | 1.394 (5) |
C10—C13 | 1.468 (5) | C39—C43 | 1.497 (5) |
C11—C12 | 1.495 (5) | C40—H40 | 0.9500 |
C12—H12A | 0.94 (3) | O7—C44 | 1.234 (6) |
C12—H12B | 0.94 (3) | N3—C44 | 1.326 (6) |
C12—H12C | 0.94 (3) | N3—C45 | 1.451 (6) |
C13—C14 | 1.393 (5) | N3—C46 | 1.456 (6) |
C13—C17 | 1.392 (5) | C44—H44 | 0.9500 |
C14—H14 | 0.9500 | C45—H45A | 0.9800 |
C14—C15 | 1.382 (6) | C45—H45B | 0.9800 |
C15—H15 | 0.9500 | C45—H45C | 0.9800 |
C16—H16 | 0.9500 | C46—H46A | 0.9800 |
C16—C17 | 1.382 (5) | C46—H46B | 0.9800 |
C17—H17 | 0.9500 | C46—H46C | 0.9800 |
C18—C19 | 1.499 (5) | O8—H8A | 0.8701 |
C18—C25 | 1.483 (5) | O8—H8B | 0.8701 |
C19—C20 | 1.390 (6) | ||
O1—Zn1—O6i | 107.22 (11) | C22—C23—H23 | 119.7 |
O1—Zn1—N1 | 118.55 (13) | C22—C23—C24 | 120.6 (4) |
O1—Zn1—N2ii | 103.86 (12) | C24—C23—H23 | 119.7 |
O6i—Zn1—N1 | 124.05 (12) | C19—C24—C23 | 120.3 (4) |
O6i—Zn1—N2ii | 101.75 (12) | C19—C24—H24 | 119.9 |
N1—Zn1—N2ii | 96.97 (12) | C23—C24—H24 | 119.9 |
C11—S1—C10 | 92.32 (19) | C26—C25—C18 | 122.6 (3) |
C28—S2—C27 | 92.20 (19) | C28—C25—C18 | 125.2 (3) |
C41—O1—Zn1 | 115.5 (3) | C28—C25—C26 | 112.1 (3) |
C42—O3—H3 | 111 (4) | C25—C26—H26 | 123.0 |
C43—O6—Zn1iii | 109.6 (2) | C27—C26—C25 | 113.9 (3) |
C15—N1—Zn1 | 118.9 (3) | C27—C26—H26 | 123.0 |
C15—N1—C16 | 118.3 (3) | C26—C27—S2 | 110.7 (3) |
C16—N1—Zn1 | 122.7 (3) | C26—C27—C30 | 127.7 (3) |
C32—N2—Zn1iv | 118.5 (3) | C30—C27—S2 | 121.5 (3) |
C32—N2—C33 | 117.6 (4) | C25—C28—S2 | 111.0 (3) |
C33—N2—Zn1iv | 122.9 (3) | C25—C28—C29 | 130.1 (4) |
C8—C1—C2 | 114.9 (3) | C29—C28—S2 | 118.9 (3) |
C18—C1—C2 | 124.1 (4) | C28—C29—H29A | 109.5 |
C18—C1—C8 | 121.0 (4) | C28—C29—H29B | 109.5 |
C3—C2—C1 | 120.5 (4) | C28—C29—H29C | 109.5 |
C3—C2—C7 | 118.5 (4) | H29A—C29—H29B | 109.5 |
C7—C2—C1 | 121.0 (4) | H29A—C29—H29C | 109.5 |
C2—C3—H3A | 119.3 | H29B—C29—H29C | 109.5 |
C2—C3—C4 | 121.4 (4) | C31—C30—C27 | 119.9 (3) |
C4—C3—H3A | 119.3 | C31—C30—C34 | 117.0 (4) |
C3—C4—H4 | 119.9 | C34—C30—C27 | 123.1 (4) |
C3—C4—C5 | 120.2 (4) | C30—C31—H31 | 120.0 |
C5—C4—H4 | 119.9 | C32—C31—C30 | 120.0 (4) |
C4—C5—H5 | 120.5 | C32—C31—H31 | 120.0 |
C4—C5—C6 | 119.1 (4) | N2—C32—C31 | 123.1 (4) |
C6—C5—H5 | 120.5 | N2—C32—H32 | 118.4 |
C5—C6—H6 | 119.8 | C31—C32—H32 | 118.4 |
C7—C6—C5 | 120.4 (4) | N2—C33—H33 | 118.6 |
C7—C6—H6 | 119.8 | N2—C33—C34 | 122.8 (4) |
C2—C7—H7 | 119.8 | C34—C33—H33 | 118.6 |
C6—C7—C2 | 120.4 (4) | C30—C34—H34 | 120.3 |
C6—C7—H7 | 119.8 | C33—C34—C30 | 119.5 (4) |
C9—C8—C1 | 123.5 (3) | C33—C34—H34 | 120.3 |
C11—C8—C1 | 124.9 (3) | C36—C35—C41 | 124.3 (4) |
C11—C8—C9 | 111.6 (3) | C40—C35—C36 | 120.0 (4) |
C8—C9—H9 | 123.1 | C40—C35—C41 | 115.7 (4) |
C10—C9—C8 | 113.9 (3) | C35—C36—C42 | 121.9 (4) |
C10—C9—H9 | 123.1 | C37—C36—C35 | 119.4 (4) |
C9—C10—S1 | 110.5 (3) | C37—C36—C42 | 118.6 (4) |
C9—C10—C13 | 128.3 (3) | C36—C37—H37 | 119.6 |
C13—C10—S1 | 121.0 (3) | C38—C37—C36 | 120.7 (4) |
C8—C11—S1 | 111.6 (3) | C38—C37—H37 | 119.6 |
C8—C11—C12 | 129.7 (4) | C37—C38—H38 | 120.1 |
C12—C11—S1 | 118.7 (3) | C37—C38—C39 | 119.9 (4) |
C11—C12—H12A | 109.5 | C39—C38—H38 | 120.1 |
C11—C12—H12B | 109.5 | C38—C39—C40 | 119.7 (4) |
C11—C12—H12C | 109.5 | C38—C39—C43 | 122.0 (4) |
H12A—C12—H12B | 109.5 | C40—C39—C43 | 118.2 (4) |
H12A—C12—H12C | 109.5 | C35—C40—C39 | 120.3 (4) |
H12B—C12—H12C | 109.5 | C35—C40—H40 | 119.9 |
C14—C13—C10 | 119.8 (3) | C39—C40—H40 | 119.9 |
C17—C13—C10 | 122.7 (3) | O1—C41—C35 | 115.4 (3) |
C17—C13—C14 | 117.4 (4) | O2—C41—O1 | 125.9 (4) |
C13—C14—H14 | 120.0 | O2—C41—C35 | 118.7 (4) |
C15—C14—C13 | 120.0 (4) | O3—C42—C36 | 112.3 (4) |
C15—C14—H14 | 120.0 | O4—C42—O3 | 125.0 (4) |
N1—C15—C14 | 122.1 (4) | O4—C42—C36 | 122.6 (4) |
N1—C15—H15 | 118.9 | O5—C43—O6 | 123.3 (4) |
C14—C15—H15 | 118.9 | O5—C43—C39 | 119.8 (4) |
N1—C16—H16 | 118.6 | O6—C43—C39 | 116.9 (3) |
N1—C16—C17 | 122.8 (3) | C44—N3—C45 | 120.9 (4) |
C17—C16—H16 | 118.6 | C44—N3—C46 | 121.6 (4) |
C13—C17—H17 | 120.4 | C45—N3—C46 | 117.5 (4) |
C16—C17—C13 | 119.2 (4) | O7—C44—N3 | 124.4 (4) |
C16—C17—H17 | 120.4 | O7—C44—H44 | 117.8 |
C1—C18—C19 | 124.0 (4) | N3—C44—H44 | 117.8 |
C1—C18—C25 | 121.5 (4) | N3—C45—H45A | 109.5 |
C25—C18—C19 | 114.5 (3) | N3—C45—H45B | 109.5 |
C20—C19—C18 | 119.3 (3) | N3—C45—H45C | 109.5 |
C20—C19—C24 | 118.5 (3) | H45A—C45—H45B | 109.5 |
C24—C19—C18 | 121.9 (3) | H45A—C45—H45C | 109.5 |
C19—C20—H20 | 119.3 | H45B—C45—H45C | 109.5 |
C19—C20—C21 | 121.3 (4) | N3—C46—H46A | 109.5 |
C21—C20—H20 | 119.3 | N3—C46—H46B | 109.5 |
C20—C21—H21 | 120.3 | N3—C46—H46C | 109.5 |
C22—C21—C20 | 119.4 (4) | H46A—C46—H46B | 109.5 |
C22—C21—H21 | 120.3 | H46A—C46—H46C | 109.5 |
C21—C22—H22 | 120.1 | H46B—C46—H46C | 109.5 |
C23—C22—C21 | 119.9 (4) | H8A—O8—H8B | 104.5 |
C23—C22—H22 | 120.1 | ||
Zn1—O1—C41—O2 | −3.8 (5) | C18—C19—C24—C23 | −173.7 (4) |
Zn1—O1—C41—C35 | 174.9 (3) | C18—C25—C26—C27 | −178.8 (3) |
Zn1iii—O6—C43—O5 | −12.5 (5) | C18—C25—C28—S2 | 179.6 (3) |
Zn1iii—O6—C43—C39 | 164.6 (3) | C18—C25—C28—C29 | 0.3 (7) |
Zn1—N1—C15—C14 | 174.0 (3) | C19—C18—C25—C26 | 129.5 (4) |
Zn1—N1—C16—C17 | −173.4 (3) | C19—C18—C25—C28 | −47.3 (5) |
Zn1iv—N2—C32—C31 | 168.0 (3) | C19—C20—C21—C22 | −0.3 (6) |
Zn1iv—N2—C33—C34 | −167.3 (3) | C20—C19—C24—C23 | 0.8 (6) |
S1—C10—C13—C14 | 175.7 (3) | C20—C21—C22—C23 | 0.8 (6) |
S1—C10—C13—C17 | −1.5 (6) | C21—C22—C23—C24 | −0.4 (6) |
S2—C27—C30—C31 | 159.2 (3) | C22—C23—C24—C19 | −0.4 (6) |
S2—C27—C30—C34 | −18.6 (5) | C24—C19—C20—C21 | −0.4 (6) |
N1—C16—C17—C13 | −0.3 (6) | C25—C18—C19—C20 | −43.0 (5) |
N2—C33—C34—C30 | −0.3 (6) | C25—C18—C19—C24 | 131.4 (4) |
C1—C2—C3—C4 | 178.5 (4) | C25—C26—C27—S2 | 0.0 (4) |
C1—C2—C7—C6 | −178.2 (4) | C25—C26—C27—C30 | 176.6 (4) |
C1—C8—C9—C10 | −179.7 (4) | C26—C25—C28—S2 | 2.6 (4) |
C1—C8—C11—S1 | 179.9 (3) | C26—C25—C28—C29 | −176.8 (4) |
C1—C8—C11—C12 | 1.0 (7) | C26—C27—C30—C31 | −17.1 (6) |
C1—C18—C19—C20 | 136.7 (4) | C26—C27—C30—C34 | 165.0 (4) |
C1—C18—C19—C24 | −48.9 (5) | C27—S2—C28—C25 | −2.2 (3) |
C1—C18—C25—C26 | −50.3 (5) | C27—S2—C28—C29 | 177.2 (3) |
C1—C18—C25—C28 | 133.0 (4) | C27—C30—C31—C32 | −177.6 (4) |
C2—C1—C8—C9 | 132.8 (4) | C27—C30—C34—C33 | 177.7 (4) |
C2—C1—C8—C11 | −46.7 (5) | C28—S2—C27—C26 | 1.3 (3) |
C2—C1—C18—C19 | −8.4 (5) | C28—S2—C27—C30 | −175.6 (3) |
C2—C1—C18—C25 | 171.4 (4) | C28—C25—C26—C27 | −1.7 (5) |
C2—C3—C4—C5 | 0.5 (6) | C30—C31—C32—N2 | 0.0 (6) |
C3—C2—C7—C6 | 0.3 (6) | C31—C30—C34—C33 | −0.2 (6) |
C3—C4—C5—C6 | −1.3 (6) | C32—N2—C33—C34 | 0.7 (6) |
C4—C5—C6—C7 | 1.5 (6) | C33—N2—C32—C31 | −0.5 (6) |
C5—C6—C7—C2 | −1.0 (6) | C34—C30—C31—C32 | 0.4 (6) |
C7—C2—C3—C4 | 0.0 (6) | C35—C36—C37—C38 | −1.8 (6) |
C8—C1—C2—C3 | −46.4 (5) | C35—C36—C42—O3 | 46.4 (5) |
C8—C1—C2—C7 | 132.0 (4) | C35—C36—C42—O4 | −137.7 (4) |
C8—C1—C18—C19 | 170.5 (4) | C36—C35—C40—C39 | 0.6 (6) |
C8—C1—C18—C25 | −9.8 (5) | C36—C35—C41—O1 | 41.0 (6) |
C8—C9—C10—S1 | −0.2 (5) | C36—C35—C41—O2 | −140.2 (4) |
C8—C9—C10—C13 | 175.6 (4) | C36—C37—C38—C39 | 1.6 (6) |
C9—C8—C11—S1 | 0.3 (5) | C37—C36—C42—O3 | −129.9 (4) |
C9—C8—C11—C12 | −178.5 (4) | C37—C36—C42—O4 | 46.0 (5) |
C9—C10—C13—C14 | 0.4 (7) | C37—C38—C39—C40 | −0.2 (6) |
C9—C10—C13—C17 | −176.8 (4) | C37—C38—C39—C43 | −176.9 (4) |
C10—S1—C11—C8 | −0.4 (3) | C38—C39—C40—C35 | −0.9 (6) |
C10—S1—C11—C12 | 178.7 (4) | C38—C39—C43—O5 | 165.5 (4) |
C10—C13—C14—C15 | −174.4 (4) | C38—C39—C43—O6 | −11.6 (5) |
C10—C13—C17—C16 | 174.8 (4) | C40—C35—C36—C37 | 0.7 (6) |
C11—S1—C10—C9 | 0.3 (3) | C40—C35—C36—C42 | −175.5 (4) |
C11—S1—C10—C13 | −175.8 (3) | C40—C35—C41—O1 | −137.8 (4) |
C11—C8—C9—C10 | −0.1 (5) | C40—C35—C41—O2 | 41.0 (5) |
C13—C14—C15—N1 | −0.7 (7) | C40—C39—C43—O5 | −11.2 (5) |
C14—C13—C17—C16 | −2.5 (6) | C40—C39—C43—O6 | 171.6 (3) |
C15—N1—C16—C17 | 2.7 (6) | C41—C35—C36—C37 | −178.0 (4) |
C16—N1—C15—C14 | −2.2 (6) | C41—C35—C36—C42 | 5.8 (6) |
C17—C13—C14—C15 | 3.0 (6) | C41—C35—C40—C39 | 179.4 (4) |
C18—C1—C2—C3 | 132.5 (4) | C42—C36—C37—C38 | 174.5 (4) |
C18—C1—C2—C7 | −49.0 (5) | C43—C39—C40—C35 | 176.0 (3) |
C18—C1—C8—C9 | −46.1 (5) | C45—N3—C44—O7 | −0.1 (8) |
C18—C1—C8—C11 | 134.3 (4) | C46—N3—C44—O7 | −179.4 (5) |
C18—C19—C20—C21 | 174.2 (4) |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x−1, y, z; (iv) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O7v | 0.85 (2) | 1.74 (3) | 2.555 (4) | 161 (7) |
O8—H8B···O5 | 0.87 | 2.01 | 2.874 (4) | 171 |
Symmetry code: (v) −x+2, −y+1, −z+1. |
C46H37N3O7S2Zn | Z = 2 |
Mr = 873.27 | F(000) = 904 |
Triclinic, P1 | Dx = 1.463 Mg m−3 |
a = 10.2620 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.2119 (12) Å | Cell parameters from 3393 reflections |
c = 18.905 (2) Å | θ = 2.3–25.7° |
α = 87.543 (3)° | µ = 0.78 mm−1 |
β = 82.666 (3)° | T = 90 K |
γ = 66.797 (3)° | Prism, colourless |
V = 1982.8 (4) Å3 | 0.04 × 0.02 × 0.02 mm |
Bruker APEX-II CCD diffractometer | Rint = 0.103 |
φ and ω scans | θmax = 26.4°, θmin = 2.0° |
8125 measured reflections | h = −12→12 |
8125 independent reflections | k = −13→14 |
5497 reflections with I > 2σ(I) | l = 0→23 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0218P)2 + 6.4705P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
8125 reflections | Δρmax = 0.56 e Å−3 |
544 parameters | Δρmin = −0.72 e Å−3 |
1 restraint |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
Zn01 | 0.37999 (6) | 0.25962 (6) | 0.46507 (3) | 0.01155 (15) | |
S1 | 0.13252 (13) | 0.74331 (13) | 0.18447 (6) | 0.0161 (3) | |
S2 | 0.76276 (13) | 0.75051 (13) | 0.19094 (6) | 0.0170 (3) | |
O1 | 0.5552 (3) | 0.1903 (3) | 0.51539 (17) | 0.0159 (7) | |
O2 | 0.6934 (3) | 0.1928 (3) | 0.41496 (17) | 0.0179 (8) | |
O3 | 1.0924 (4) | −0.1205 (4) | 0.68269 (18) | 0.0218 (8) | |
H3 | 1.146 (5) | −0.135 (5) | 0.6442 (17) | 0.026* | |
O4 | 0.8692 (4) | −0.0191 (4) | 0.72930 (18) | 0.0243 (9) | |
O5 | 1.2436 (3) | 0.1969 (3) | 0.52556 (17) | 0.0151 (7) | |
O6 | 1.1017 (3) | 0.3132 (3) | 0.44659 (17) | 0.0190 (8) | |
O7 | 0.3034 (3) | 0.4251 (3) | 0.53566 (17) | 0.0182 (8) | |
N1 | 0.3691 (4) | 0.3917 (4) | 0.38172 (19) | 0.0131 (9) | |
N2 | 0.4288 (4) | 1.1105 (4) | 0.38622 (19) | 0.0129 (9) | |
N3 | 0.1860 (4) | 0.5014 (4) | 0.6442 (2) | 0.0196 (10) | |
C00I | 0.8966 (5) | 0.2107 (4) | 0.4964 (2) | 0.0125 (10) | |
H00I | 0.882410 | 0.262475 | 0.454711 | 0.015* | |
C1 | 0.4268 (5) | 0.7433 (5) | 0.0221 (2) | 0.0131 (11) | |
C2 | 0.3628 (5) | 0.7507 (5) | −0.0453 (2) | 0.0139 (11) | |
C3 | 0.2999 (5) | 0.6664 (5) | −0.0577 (2) | 0.0154 (11) | |
H3A | 0.304793 | 0.598818 | −0.024762 | 0.018* | |
C4 | 0.2294 (5) | 0.6780 (5) | −0.1174 (3) | 0.0184 (12) | |
H4 | 0.187504 | 0.618449 | −0.125048 | 0.022* | |
C5 | 0.2204 (5) | 0.7762 (6) | −0.1656 (3) | 0.0221 (13) | |
H5 | 0.170877 | 0.785464 | −0.205975 | 0.026* | |
C6 | 0.2845 (5) | 0.8619 (5) | −0.1546 (3) | 0.0199 (12) | |
H6 | 0.278966 | 0.929485 | −0.187649 | 0.024* | |
C7 | 0.3561 (5) | 0.8483 (5) | −0.0955 (2) | 0.0152 (11) | |
H7 | 0.401293 | 0.905735 | −0.088778 | 0.018* | |
C8 | 0.3393 (5) | 0.7256 (5) | 0.0881 (2) | 0.0136 (11) | |
C9 | 0.3977 (5) | 0.6350 (5) | 0.1423 (2) | 0.0123 (10) | |
H9 | 0.496213 | 0.580036 | 0.139362 | 0.015* | |
C10 | 0.3016 (5) | 0.6332 (5) | 0.1984 (2) | 0.0133 (11) | |
C11 | 0.1932 (5) | 0.7897 (5) | 0.1030 (2) | 0.0136 (11) | |
C12 | 0.0869 (5) | 0.8892 (5) | 0.0612 (3) | 0.0183 (12) | |
H12A | 0.053 (3) | 0.8472 (13) | 0.0301 (16) | 0.027* | |
H12B | 0.1311 (16) | 0.939 (3) | 0.0343 (16) | 0.027* | |
H12C | 0.010 (3) | 0.944 (3) | 0.0927 (9) | 0.027* | |
C13 | 0.3242 (5) | 0.5526 (5) | 0.2619 (2) | 0.0130 (10) | |
C14 | 0.4386 (5) | 0.4324 (5) | 0.2604 (2) | 0.0147 (11) | |
H14 | 0.503028 | 0.402805 | 0.218007 | 0.018* | |
C15 | 0.4578 (5) | 0.3567 (5) | 0.3204 (2) | 0.0119 (10) | |
H15 | 0.537461 | 0.275877 | 0.318629 | 0.014* | |
C16 | 0.2604 (5) | 0.5070 (5) | 0.3833 (2) | 0.0160 (11) | |
H16 | 0.197480 | 0.534024 | 0.426345 | 0.019* | |
C17 | 0.2348 (5) | 0.5889 (5) | 0.3256 (2) | 0.0162 (11) | |
H17 | 0.155864 | 0.670331 | 0.329464 | 0.019* | |
C18 | 0.5546 (5) | 0.7519 (5) | 0.0252 (2) | 0.0110 (10) | |
C19 | 0.6538 (5) | 0.7497 (5) | −0.0402 (2) | 0.0139 (11) | |
C20 | 0.7114 (5) | 0.8448 (5) | −0.0492 (3) | 0.0175 (12) | |
H20 | 0.684153 | 0.911837 | −0.014566 | 0.021* | |
C21 | 0.8078 (5) | 0.8416 (5) | −0.1084 (3) | 0.0196 (12) | |
H21 | 0.845335 | 0.906891 | −0.114664 | 0.024* | |
C22 | 0.8490 (5) | 0.7429 (5) | −0.1584 (3) | 0.0179 (12) | |
H22 | 0.915930 | 0.740087 | −0.198624 | 0.022* | |
C23 | 0.7940 (5) | 0.6488 (5) | −0.1503 (2) | 0.0171 (11) | |
H23 | 0.823274 | 0.581029 | −0.184674 | 0.020* | |
C24 | 0.6957 (5) | 0.6527 (5) | −0.0919 (2) | 0.0139 (11) | |
H24 | 0.656530 | 0.588405 | −0.087081 | 0.017* | |
C25 | 0.6046 (5) | 0.7672 (5) | 0.0935 (2) | 0.0141 (11) | |
C26 | 0.5168 (5) | 0.8539 (5) | 0.1494 (2) | 0.0112 (10) | |
H26 | 0.418486 | 0.905582 | 0.147261 | 0.013* | |
C27 | 0.5847 (5) | 0.8569 (5) | 0.2056 (2) | 0.0133 (10) | |
C28 | 0.7441 (5) | 0.7040 (5) | 0.1086 (2) | 0.0150 (11) | |
C29 | 0.8723 (5) | 0.6084 (5) | 0.0651 (3) | 0.0205 (12) | |
H29A | 0.916 (2) | 0.6547 (14) | 0.0323 (16) | 0.031* | |
H29B | 0.8431 (11) | 0.553 (3) | 0.0383 (16) | 0.031* | |
H29C | 0.940 (3) | 0.556 (3) | 0.0965 (9) | 0.031* | |
C30 | 0.5313 (5) | 0.9393 (5) | 0.2694 (2) | 0.0125 (10) | |
C31 | 0.4060 (5) | 1.0506 (5) | 0.2702 (2) | 0.0146 (11) | |
H31 | 0.353328 | 1.070080 | 0.230391 | 0.017* | |
C32 | 0.3587 (5) | 1.1321 (5) | 0.3286 (2) | 0.0130 (10) | |
H32 | 0.272652 | 1.207109 | 0.328123 | 0.016* | |
C33 | 0.5464 (5) | 1.0016 (5) | 0.3869 (2) | 0.0150 (11) | |
H33 | 0.595537 | 0.983526 | 0.427857 | 0.018* | |
C34 | 0.5993 (5) | 0.9148 (5) | 0.3308 (2) | 0.0137 (10) | |
H34 | 0.682356 | 0.837903 | 0.334040 | 0.016* | |
C35 | 0.7939 (5) | 0.1625 (4) | 0.5238 (2) | 0.0119 (10) | |
C36 | 0.8127 (5) | 0.0902 (4) | 0.5856 (2) | 0.0125 (10) | |
H36 | 0.740189 | 0.062786 | 0.606880 | 0.015* | |
C37 | 0.9383 (5) | 0.0577 (5) | 0.6167 (2) | 0.0146 (11) | |
C38 | 1.0407 (5) | 0.1048 (5) | 0.5885 (2) | 0.0142 (10) | |
H38 | 1.126013 | 0.082508 | 0.609909 | 0.017* | |
C39 | 1.0181 (5) | 0.1848 (4) | 0.5286 (2) | 0.0107 (10) | |
C40 | 0.6708 (5) | 0.1851 (5) | 0.4816 (2) | 0.0157 (11) | |
C41 | 0.9618 (5) | −0.0299 (5) | 0.6808 (3) | 0.0180 (11) | |
C42 | 1.1274 (5) | 0.2361 (5) | 0.4973 (2) | 0.0122 (10) | |
C43 | 0.1939 (5) | 0.4578 (5) | 0.5792 (3) | 0.0185 (11) | |
H43 | 0.111407 | 0.451045 | 0.565162 | 0.022* | |
C44 | 0.3068 (6) | 0.5165 (6) | 0.6686 (3) | 0.0330 (15) | |
H44A | 0.396 (3) | 0.471 (3) | 0.6334 (15) | 0.049* | |
H44B | 0.322 (3) | 0.476 (3) | 0.7181 (17) | 0.049* | |
H44C | 0.2870 (18) | 0.613 (3) | 0.6718 (19) | 0.049* | |
C45 | 0.0494 (6) | 0.5553 (6) | 0.6892 (3) | 0.0272 (13) | |
H45A | 0.020 (2) | 0.654 (3) | 0.6959 (15) | 0.041* | |
H45B | 0.0589 (12) | 0.510 (3) | 0.7387 (16) | 0.041* | |
H45C | −0.028 (2) | 0.540 (3) | 0.6652 (11) | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn01 | 0.0071 (3) | 0.0168 (3) | 0.0123 (3) | −0.0062 (3) | −0.0026 (2) | 0.0026 (2) |
S1 | 0.0086 (6) | 0.0207 (8) | 0.0164 (6) | −0.0033 (6) | −0.0016 (5) | 0.0035 (5) |
S2 | 0.0099 (6) | 0.0211 (8) | 0.0184 (6) | −0.0034 (6) | −0.0044 (5) | −0.0017 (5) |
O1 | 0.0078 (17) | 0.022 (2) | 0.0188 (17) | −0.0065 (16) | −0.0035 (14) | 0.0026 (14) |
O2 | 0.0146 (18) | 0.027 (2) | 0.0167 (18) | −0.0118 (17) | −0.0072 (14) | 0.0053 (15) |
O3 | 0.016 (2) | 0.029 (2) | 0.0186 (19) | −0.0075 (18) | −0.0059 (15) | 0.0109 (16) |
O4 | 0.0153 (19) | 0.040 (3) | 0.0214 (19) | −0.0159 (19) | −0.0009 (16) | 0.0087 (17) |
O5 | 0.0081 (17) | 0.0202 (19) | 0.0202 (18) | −0.0089 (15) | −0.0036 (14) | 0.0049 (14) |
O6 | 0.0137 (18) | 0.025 (2) | 0.0213 (19) | −0.0102 (17) | −0.0074 (14) | 0.0097 (15) |
O7 | 0.0156 (19) | 0.021 (2) | 0.0188 (18) | −0.0096 (17) | 0.0040 (15) | −0.0029 (15) |
N1 | 0.007 (2) | 0.020 (2) | 0.012 (2) | −0.0054 (19) | −0.0028 (16) | 0.0029 (17) |
N2 | 0.013 (2) | 0.014 (2) | 0.014 (2) | −0.0074 (19) | −0.0021 (16) | −0.0004 (16) |
N3 | 0.021 (2) | 0.020 (3) | 0.018 (2) | −0.009 (2) | −0.0013 (18) | −0.0049 (18) |
C00I | 0.012 (3) | 0.013 (3) | 0.012 (2) | −0.004 (2) | −0.0015 (19) | −0.0011 (19) |
C1 | 0.015 (3) | 0.011 (3) | 0.013 (2) | −0.005 (2) | −0.0025 (19) | 0.0014 (19) |
C2 | 0.010 (3) | 0.017 (3) | 0.014 (2) | −0.004 (2) | −0.0049 (19) | −0.001 (2) |
C3 | 0.016 (3) | 0.017 (3) | 0.015 (2) | −0.007 (2) | −0.006 (2) | 0.001 (2) |
C4 | 0.014 (3) | 0.024 (3) | 0.020 (3) | −0.010 (3) | −0.003 (2) | −0.001 (2) |
C5 | 0.014 (3) | 0.036 (4) | 0.013 (3) | −0.006 (3) | −0.005 (2) | 0.002 (2) |
C6 | 0.016 (3) | 0.025 (3) | 0.015 (3) | −0.005 (3) | −0.001 (2) | 0.007 (2) |
C7 | 0.009 (3) | 0.019 (3) | 0.017 (2) | −0.005 (2) | −0.0012 (19) | 0.002 (2) |
C8 | 0.011 (3) | 0.020 (3) | 0.014 (2) | −0.010 (2) | −0.0057 (19) | 0.001 (2) |
C9 | 0.006 (2) | 0.013 (3) | 0.018 (2) | −0.002 (2) | −0.0071 (19) | 0.002 (2) |
C10 | 0.005 (2) | 0.015 (3) | 0.018 (3) | −0.002 (2) | −0.0031 (19) | −0.002 (2) |
C11 | 0.013 (3) | 0.017 (3) | 0.015 (2) | −0.009 (2) | −0.0039 (19) | 0.000 (2) |
C12 | 0.012 (3) | 0.019 (3) | 0.022 (3) | −0.003 (3) | −0.005 (2) | 0.006 (2) |
C13 | 0.010 (2) | 0.018 (3) | 0.014 (2) | −0.008 (2) | −0.0048 (19) | 0.002 (2) |
C14 | 0.011 (3) | 0.023 (3) | 0.013 (2) | −0.009 (2) | −0.0017 (19) | −0.001 (2) |
C15 | 0.007 (2) | 0.014 (3) | 0.016 (2) | −0.005 (2) | −0.0043 (19) | 0.0007 (19) |
C16 | 0.016 (3) | 0.021 (3) | 0.013 (2) | −0.010 (2) | 0.000 (2) | −0.002 (2) |
C17 | 0.012 (3) | 0.014 (3) | 0.021 (3) | −0.003 (2) | −0.003 (2) | 0.003 (2) |
C18 | 0.010 (2) | 0.007 (3) | 0.014 (2) | −0.001 (2) | −0.0010 (18) | −0.0007 (19) |
C19 | 0.010 (3) | 0.012 (3) | 0.017 (3) | 0.000 (2) | −0.0073 (19) | 0.001 (2) |
C20 | 0.016 (3) | 0.022 (3) | 0.017 (3) | −0.010 (3) | −0.004 (2) | 0.002 (2) |
C21 | 0.020 (3) | 0.023 (3) | 0.022 (3) | −0.014 (3) | −0.005 (2) | 0.007 (2) |
C22 | 0.009 (3) | 0.024 (3) | 0.018 (3) | −0.003 (2) | −0.002 (2) | 0.003 (2) |
C23 | 0.014 (3) | 0.022 (3) | 0.015 (3) | −0.006 (3) | −0.004 (2) | −0.001 (2) |
C24 | 0.008 (2) | 0.015 (3) | 0.020 (3) | −0.006 (2) | −0.0036 (19) | 0.000 (2) |
C25 | 0.013 (3) | 0.020 (3) | 0.013 (2) | −0.009 (2) | −0.0030 (19) | 0.003 (2) |
C26 | 0.005 (2) | 0.010 (3) | 0.018 (2) | −0.003 (2) | −0.0040 (18) | 0.0014 (19) |
C27 | 0.014 (3) | 0.013 (3) | 0.014 (2) | −0.006 (2) | −0.0034 (19) | 0.0008 (19) |
C28 | 0.015 (3) | 0.015 (3) | 0.016 (2) | −0.008 (2) | 0.000 (2) | 0.001 (2) |
C29 | 0.011 (3) | 0.024 (3) | 0.022 (3) | −0.001 (3) | −0.003 (2) | −0.002 (2) |
C30 | 0.006 (2) | 0.019 (3) | 0.016 (2) | −0.007 (2) | −0.0015 (18) | 0.001 (2) |
C31 | 0.006 (2) | 0.026 (3) | 0.016 (2) | −0.010 (2) | −0.0036 (19) | 0.002 (2) |
C32 | 0.009 (2) | 0.014 (3) | 0.016 (2) | −0.005 (2) | −0.0017 (19) | 0.002 (2) |
C33 | 0.017 (3) | 0.020 (3) | 0.013 (2) | −0.011 (2) | −0.005 (2) | 0.005 (2) |
C34 | 0.009 (2) | 0.015 (3) | 0.017 (2) | −0.005 (2) | −0.0023 (19) | 0.005 (2) |
C35 | 0.009 (2) | 0.013 (3) | 0.014 (2) | −0.004 (2) | −0.0021 (18) | −0.0003 (19) |
C36 | 0.007 (2) | 0.014 (3) | 0.019 (2) | −0.008 (2) | 0.0010 (19) | 0.001 (2) |
C37 | 0.010 (3) | 0.020 (3) | 0.015 (2) | −0.007 (2) | −0.0025 (19) | 0.001 (2) |
C38 | 0.012 (3) | 0.019 (3) | 0.014 (2) | −0.007 (2) | −0.0032 (19) | 0.000 (2) |
C39 | 0.009 (2) | 0.009 (2) | 0.014 (2) | −0.004 (2) | −0.0011 (18) | −0.0032 (18) |
C40 | 0.016 (3) | 0.016 (3) | 0.017 (3) | −0.007 (2) | −0.004 (2) | 0.002 (2) |
C41 | 0.017 (3) | 0.021 (3) | 0.022 (3) | −0.012 (3) | −0.011 (2) | 0.004 (2) |
C42 | 0.008 (2) | 0.013 (3) | 0.015 (2) | −0.005 (2) | 0.0009 (19) | −0.0008 (19) |
C43 | 0.021 (3) | 0.014 (3) | 0.020 (3) | −0.005 (2) | −0.008 (2) | 0.003 (2) |
C44 | 0.024 (3) | 0.050 (4) | 0.030 (3) | −0.018 (3) | −0.010 (3) | −0.005 (3) |
C45 | 0.020 (3) | 0.026 (3) | 0.029 (3) | −0.003 (3) | −0.001 (2) | −0.004 (2) |
Zn01—O1 | 2.003 (3) | C14—H14 | 0.9500 |
Zn01—O5i | 2.015 (3) | C14—C15 | 1.375 (6) |
Zn01—O7 | 2.153 (3) | C15—H15 | 0.9500 |
Zn01—N1 | 2.098 (4) | C16—H16 | 0.9500 |
Zn01—N2ii | 2.152 (4) | C16—C17 | 1.379 (6) |
S1—C10 | 1.733 (5) | C17—H17 | 0.9500 |
S1—C11 | 1.724 (5) | C18—C19 | 1.493 (6) |
S2—C27 | 1.738 (5) | C18—C25 | 1.489 (6) |
S2—C28 | 1.719 (5) | C19—C20 | 1.403 (7) |
O1—C40 | 1.254 (5) | C19—C24 | 1.392 (7) |
O2—C40 | 1.258 (5) | C20—H20 | 0.9500 |
O3—H3 | 0.835 (19) | C20—C21 | 1.388 (7) |
O3—C41 | 1.329 (6) | C21—H21 | 0.9500 |
O4—C41 | 1.206 (6) | C21—C22 | 1.383 (7) |
O5—C42 | 1.277 (5) | C22—H22 | 0.9500 |
O6—C42 | 1.245 (5) | C22—C23 | 1.374 (7) |
O7—C43 | 1.241 (6) | C23—H23 | 0.9500 |
N1—C15 | 1.346 (6) | C23—C24 | 1.386 (6) |
N1—C16 | 1.332 (6) | C24—H24 | 0.9500 |
N2—C32 | 1.343 (6) | C25—C26 | 1.424 (7) |
N2—C33 | 1.337 (6) | C25—C28 | 1.386 (7) |
N3—C43 | 1.323 (6) | C26—H26 | 0.9500 |
N3—C44 | 1.447 (6) | C26—C27 | 1.351 (6) |
N3—C45 | 1.458 (6) | C27—C30 | 1.463 (7) |
C00I—H00I | 0.9500 | C28—C29 | 1.498 (7) |
C00I—C35 | 1.399 (6) | C29—H29A | 0.97 (3) |
C00I—C39 | 1.379 (6) | C29—H29B | 0.97 (3) |
C1—C2 | 1.492 (6) | C29—H29C | 0.97 (3) |
C1—C8 | 1.496 (6) | C30—C31 | 1.394 (7) |
C1—C18 | 1.361 (6) | C30—C34 | 1.393 (6) |
C2—C3 | 1.380 (7) | C31—H31 | 0.9500 |
C2—C7 | 1.403 (7) | C31—C32 | 1.375 (7) |
C3—H3A | 0.9500 | C32—H32 | 0.9500 |
C3—C4 | 1.391 (6) | C33—H33 | 0.9500 |
C4—H4 | 0.9500 | C33—C34 | 1.375 (7) |
C4—C5 | 1.380 (7) | C34—H34 | 0.9500 |
C5—H5 | 0.9500 | C35—C36 | 1.384 (6) |
C5—C6 | 1.395 (7) | C35—C40 | 1.510 (6) |
C6—H6 | 0.9500 | C36—H36 | 0.9500 |
C6—C7 | 1.386 (6) | C36—C37 | 1.394 (6) |
C7—H7 | 0.9500 | C37—C38 | 1.392 (6) |
C8—C9 | 1.424 (6) | C37—C41 | 1.510 (6) |
C8—C11 | 1.380 (7) | C38—H38 | 0.9500 |
C9—H9 | 0.9500 | C38—C39 | 1.399 (6) |
C9—C10 | 1.359 (6) | C39—C42 | 1.500 (6) |
C10—C13 | 1.457 (6) | C43—H43 | 0.9500 |
C11—C12 | 1.498 (6) | C44—H44A | 1.03 (3) |
C12—H12A | 0.94 (3) | C44—H44B | 1.03 (3) |
C12—H12B | 0.94 (3) | C44—H44C | 1.03 (3) |
C12—H12C | 0.94 (3) | C45—H45A | 1.04 (3) |
C13—C14 | 1.395 (7) | C45—H45B | 1.04 (3) |
C13—C17 | 1.387 (6) | C45—H45C | 1.04 (3) |
O1—Zn01—O5i | 103.25 (13) | C19—C20—H20 | 119.8 |
O1—Zn01—O7 | 87.20 (13) | C21—C20—C19 | 120.4 (5) |
O1—Zn01—N1 | 118.89 (14) | C21—C20—H20 | 119.8 |
O1—Zn01—N2ii | 101.45 (14) | C20—C21—H21 | 120.1 |
O5i—Zn01—O7 | 87.18 (13) | C22—C21—C20 | 119.8 (5) |
O5i—Zn01—N1 | 136.91 (14) | C22—C21—H21 | 120.1 |
O5i—Zn01—N2ii | 91.89 (14) | C21—C22—H22 | 119.7 |
N1—Zn01—O7 | 86.32 (14) | C23—C22—C21 | 120.5 (5) |
N1—Zn01—N2ii | 88.45 (15) | C23—C22—H22 | 119.7 |
N2ii—Zn01—O7 | 171.28 (14) | C22—C23—H23 | 120.0 |
C11—S1—C10 | 92.8 (2) | C22—C23—C24 | 120.0 (5) |
C28—S2—C27 | 92.8 (2) | C24—C23—H23 | 120.0 |
C40—O1—Zn01 | 118.1 (3) | C19—C24—H24 | 119.6 |
C41—O3—H3 | 116 (4) | C23—C24—C19 | 120.7 (5) |
C42—O5—Zn01iii | 108.0 (3) | C23—C24—H24 | 119.6 |
C43—O7—Zn01 | 125.2 (3) | C26—C25—C18 | 124.0 (4) |
C15—N1—Zn01 | 121.5 (3) | C28—C25—C18 | 123.9 (4) |
C16—N1—Zn01 | 120.6 (3) | C28—C25—C26 | 111.9 (4) |
C16—N1—C15 | 117.1 (4) | C25—C26—H26 | 122.7 |
C32—N2—Zn01iv | 121.5 (3) | C27—C26—C25 | 114.5 (4) |
C33—N2—Zn01iv | 120.0 (3) | C27—C26—H26 | 122.7 |
C33—N2—C32 | 117.5 (4) | C26—C27—S2 | 110.0 (4) |
C43—N3—C44 | 121.2 (5) | C26—C27—C30 | 129.4 (4) |
C43—N3—C45 | 120.8 (4) | C30—C27—S2 | 120.4 (3) |
C44—N3—C45 | 117.3 (4) | C25—C28—S2 | 110.7 (4) |
C35—C00I—H00I | 119.3 | C25—C28—C29 | 130.4 (4) |
C39—C00I—H00I | 119.3 | C29—C28—S2 | 119.0 (4) |
C39—C00I—C35 | 121.4 (4) | C28—C29—H29A | 109.5 |
C2—C1—C8 | 114.9 (4) | C28—C29—H29B | 109.5 |
C18—C1—C2 | 124.0 (4) | C28—C29—H29C | 109.5 |
C18—C1—C8 | 121.1 (4) | H29A—C29—H29B | 109.5 |
C3—C2—C1 | 120.5 (4) | H29A—C29—H29C | 109.5 |
C3—C2—C7 | 118.2 (4) | H29B—C29—H29C | 109.5 |
C7—C2—C1 | 121.2 (5) | C31—C30—C27 | 119.5 (4) |
C2—C3—H3A | 119.2 | C34—C30—C27 | 123.9 (4) |
C2—C3—C4 | 121.5 (5) | C34—C30—C31 | 116.6 (4) |
C4—C3—H3A | 119.2 | C30—C31—H31 | 120.0 |
C3—C4—H4 | 120.0 | C32—C31—C30 | 120.0 (4) |
C5—C4—C3 | 120.0 (5) | C32—C31—H31 | 120.0 |
C5—C4—H4 | 120.0 | N2—C32—C31 | 122.9 (4) |
C4—C5—H5 | 120.2 | N2—C32—H32 | 118.6 |
C4—C5—C6 | 119.6 (5) | C31—C32—H32 | 118.6 |
C6—C5—H5 | 120.2 | N2—C33—H33 | 118.5 |
C5—C6—H6 | 120.0 | N2—C33—C34 | 123.0 (4) |
C7—C6—C5 | 120.0 (5) | C34—C33—H33 | 118.5 |
C7—C6—H6 | 120.0 | C30—C34—H34 | 120.0 |
C2—C7—H7 | 119.6 | C33—C34—C30 | 120.0 (5) |
C6—C7—C2 | 120.8 (5) | C33—C34—H34 | 120.0 |
C6—C7—H7 | 119.6 | C00I—C35—C40 | 118.1 (4) |
C9—C8—C1 | 123.3 (4) | C36—C35—C00I | 119.3 (4) |
C11—C8—C1 | 125.0 (4) | C36—C35—C40 | 122.6 (4) |
C11—C8—C9 | 111.7 (4) | C35—C36—H36 | 120.1 |
C8—C9—H9 | 122.6 | C35—C36—C37 | 119.8 (4) |
C10—C9—C8 | 114.8 (4) | C37—C36—H36 | 120.1 |
C10—C9—H9 | 122.6 | C36—C37—C41 | 119.0 (4) |
C9—C10—S1 | 109.7 (3) | C38—C37—C36 | 120.3 (4) |
C9—C10—C13 | 129.2 (4) | C38—C37—C41 | 120.6 (4) |
C13—C10—S1 | 121.1 (4) | C37—C38—H38 | 120.0 |
C8—C11—S1 | 110.9 (4) | C37—C38—C39 | 120.0 (4) |
C8—C11—C12 | 130.7 (4) | C39—C38—H38 | 120.0 |
C12—C11—S1 | 118.5 (4) | C00I—C39—C38 | 118.9 (4) |
C11—C12—H12A | 109.5 | C00I—C39—C42 | 120.2 (4) |
C11—C12—H12B | 109.5 | C38—C39—C42 | 120.8 (4) |
C11—C12—H12C | 109.5 | O1—C40—O2 | 124.8 (4) |
H12A—C12—H12B | 109.5 | O1—C40—C35 | 117.7 (4) |
H12A—C12—H12C | 109.5 | O2—C40—C35 | 117.4 (4) |
H12B—C12—H12C | 109.5 | O3—C41—C37 | 116.8 (4) |
C14—C13—C10 | 120.3 (4) | O4—C41—O3 | 120.2 (4) |
C17—C13—C10 | 122.9 (4) | O4—C41—C37 | 123.0 (5) |
C17—C13—C14 | 116.7 (4) | O5—C42—C39 | 116.5 (4) |
C13—C14—H14 | 120.1 | O6—C42—O5 | 123.7 (4) |
C15—C14—C13 | 119.7 (4) | O6—C42—C39 | 119.8 (4) |
C15—C14—H14 | 120.1 | O7—C43—N3 | 123.5 (5) |
N1—C15—C14 | 123.2 (4) | O7—C43—H43 | 118.3 |
N1—C15—H15 | 118.4 | N3—C43—H43 | 118.3 |
C14—C15—H15 | 118.4 | N3—C44—H44A | 109.5 |
N1—C16—H16 | 118.4 | N3—C44—H44B | 109.5 |
N1—C16—C17 | 123.1 (5) | N3—C44—H44C | 109.5 |
C17—C16—H16 | 118.4 | H44A—C44—H44B | 109.5 |
C13—C17—H17 | 120.0 | H44A—C44—H44C | 109.5 |
C16—C17—C13 | 120.1 (5) | H44B—C44—H44C | 109.5 |
C16—C17—H17 | 120.0 | N3—C45—H45A | 109.5 |
C1—C18—C19 | 122.2 (4) | N3—C45—H45B | 109.5 |
C1—C18—C25 | 122.8 (4) | N3—C45—H45C | 109.5 |
C25—C18—C19 | 115.0 (4) | H45A—C45—H45B | 109.5 |
C20—C19—C18 | 119.7 (4) | H45A—C45—H45C | 109.5 |
C24—C19—C18 | 121.8 (5) | H45B—C45—H45C | 109.5 |
C24—C19—C20 | 118.5 (5) | ||
Zn01—O1—C40—O2 | −16.3 (7) | C17—C13—C14—C15 | −0.1 (7) |
Zn01—O1—C40—C35 | 166.3 (3) | C18—C1—C2—C3 | 136.9 (5) |
Zn01iii—O5—C42—O6 | −8.2 (6) | C18—C1—C2—C7 | −47.4 (7) |
Zn01iii—O5—C42—C39 | 172.0 (3) | C18—C1—C8—C9 | −45.4 (7) |
Zn01—O7—C43—N3 | 139.8 (4) | C18—C1—C8—C11 | 137.5 (5) |
Zn01—N1—C15—C14 | 168.4 (3) | C18—C19—C20—C21 | 177.6 (4) |
Zn01—N1—C16—C17 | −169.2 (4) | C18—C19—C24—C23 | −176.5 (4) |
Zn01iv—N2—C32—C31 | 165.6 (3) | C18—C25—C26—C27 | −177.3 (4) |
Zn01iv—N2—C33—C34 | −166.6 (3) | C18—C25—C28—S2 | 177.6 (4) |
S1—C10—C13—C14 | 152.9 (4) | C18—C25—C28—C29 | −1.6 (8) |
S1—C10—C13—C17 | −26.4 (6) | C19—C18—C25—C26 | 134.4 (5) |
S2—C27—C30—C31 | 159.4 (4) | C19—C18—C25—C28 | −41.8 (7) |
S2—C27—C30—C34 | −19.8 (6) | C19—C20—C21—C22 | −0.9 (7) |
N1—C16—C17—C13 | 0.1 (7) | C20—C19—C24—C23 | 1.1 (7) |
N2—C33—C34—C30 | 1.1 (7) | C20—C21—C22—C23 | 0.8 (7) |
C00I—C35—C36—C37 | −5.0 (7) | C21—C22—C23—C24 | 0.4 (7) |
C00I—C35—C40—O1 | −152.5 (4) | C22—C23—C24—C19 | −1.3 (7) |
C00I—C35—C40—O2 | 29.8 (7) | C24—C19—C20—C21 | 0.0 (7) |
C00I—C39—C42—O5 | −172.8 (4) | C25—C18—C19—C20 | −48.0 (6) |
C00I—C39—C42—O6 | 7.4 (7) | C25—C18—C19—C24 | 129.6 (5) |
C1—C2—C3—C4 | 174.7 (5) | C25—C26—C27—S2 | 0.1 (5) |
C1—C2—C7—C6 | −173.8 (4) | C25—C26—C27—C30 | 175.7 (5) |
C1—C8—C9—C10 | 179.8 (5) | C26—C25—C28—S2 | 1.0 (5) |
C1—C8—C11—S1 | −179.7 (4) | C26—C25—C28—C29 | −178.1 (5) |
C1—C8—C11—C12 | −0.6 (9) | C26—C27—C30—C31 | −15.8 (8) |
C1—C18—C19—C20 | 130.6 (5) | C26—C27—C30—C34 | 164.9 (5) |
C1—C18—C19—C24 | −51.8 (7) | C27—S2—C28—C25 | −0.9 (4) |
C1—C18—C25—C26 | −44.2 (7) | C27—S2—C28—C29 | 178.4 (4) |
C1—C18—C25—C28 | 139.6 (5) | C27—C30—C31—C32 | −176.8 (4) |
C2—C1—C8—C9 | 134.8 (5) | C27—C30—C34—C33 | 176.0 (4) |
C2—C1—C8—C11 | −42.4 (7) | C28—S2—C27—C26 | 0.5 (4) |
C2—C1—C18—C19 | −9.4 (8) | C28—S2—C27—C30 | −175.6 (4) |
C2—C1—C18—C25 | 169.1 (5) | C28—C25—C26—C27 | −0.7 (6) |
C2—C3—C4—C5 | −0.5 (8) | C30—C31—C32—N2 | 0.5 (7) |
C3—C2—C7—C6 | 1.9 (7) | C31—C30—C34—C33 | −3.2 (7) |
C3—C4—C5—C6 | 1.1 (8) | C32—N2—C33—C34 | 1.9 (7) |
C4—C5—C6—C7 | −0.2 (8) | C33—N2—C32—C31 | −2.7 (7) |
C5—C6—C7—C2 | −1.3 (8) | C34—C30—C31—C32 | 2.5 (7) |
C7—C2—C3—C4 | −1.1 (7) | C35—C00I—C39—C38 | 2.2 (7) |
C8—C1—C2—C3 | −43.3 (7) | C35—C00I—C39—C42 | 179.1 (4) |
C8—C1—C2—C7 | 132.4 (5) | C35—C36—C37—C38 | 4.2 (7) |
C8—C1—C18—C19 | 170.8 (5) | C35—C36—C37—C41 | −175.3 (4) |
C8—C1—C18—C25 | −10.7 (8) | C36—C35—C40—O1 | 31.3 (7) |
C8—C9—C10—S1 | 1.3 (6) | C36—C35—C40—O2 | −146.4 (5) |
C8—C9—C10—C13 | 179.3 (5) | C36—C37—C38—C39 | −0.2 (7) |
C9—C8—C11—S1 | 2.8 (5) | C36—C37—C41—O3 | 138.6 (5) |
C9—C8—C11—C12 | −178.0 (5) | C36—C37—C41—O4 | −42.5 (7) |
C9—C10—C13—C14 | −24.9 (8) | C37—C38—C39—C00I | −3.0 (7) |
C9—C10—C13—C17 | 155.9 (5) | C37—C38—C39—C42 | −179.8 (4) |
C10—S1—C11—C8 | −1.8 (4) | C38—C37—C41—O3 | −40.9 (7) |
C10—S1—C11—C12 | 178.9 (4) | C38—C37—C41—O4 | 138.0 (5) |
C10—C13—C14—C15 | −179.3 (4) | C38—C39—C42—O5 | 4.0 (7) |
C10—C13—C17—C16 | 178.7 (4) | C38—C39—C42—O6 | −175.8 (4) |
C11—S1—C10—C9 | 0.3 (4) | C39—C00I—C35—C36 | 1.8 (7) |
C11—S1—C10—C13 | −177.9 (4) | C39—C00I—C35—C40 | −174.5 (4) |
C11—C8—C9—C10 | −2.8 (6) | C40—C35—C36—C37 | 171.1 (5) |
C13—C14—C15—N1 | 1.3 (7) | C41—C37—C38—C39 | 179.3 (4) |
C14—C13—C17—C16 | −0.6 (7) | C44—N3—C43—O7 | 1.2 (8) |
C15—N1—C16—C17 | 1.0 (7) | C45—N3—C43—O7 | 171.3 (5) |
C16—N1—C15—C14 | −1.7 (6) |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) x+1, y, z; (iv) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2v | 0.84 (2) | 1.77 (3) | 2.566 (5) | 159 (5) |
Symmetry code: (v) −x+2, −y, −z+1. |
C48H34N2O4S2Zn·2(H2O)·[+solvents]0.167[] | Dx = 0.927 Mg m−3 |
Mr = 868.29 | Mo Kα radiation, λ = 0.71073 Å |
Hexagonal, P6422 | Cell parameters from 9909 reflections |
a = 15.4656 (4) Å | θ = 2.4–21.0° |
c = 45.0635 (14) Å | µ = 0.50 mm−1 |
V = 9334.5 (5) Å3 | T = 90 K |
Z = 6 | Prism, colourless |
F(000) = 2700 | 0.17 × 0.16 × 0.12 mm |
Bruker APEX-II CCD diffractometer | 7354 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.085 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.2117 before and 0.0526 after correction. The Ratio of minimum to maximum transmission is 0.9078. The λ/2 correction factor is Not present. | θmax = 30.6°, θmin = 1.6° |
Tmin = 0.677, Tmax = 0.746 | h = −22→22 |
222145 measured reflections | k = −22→22 |
9557 independent reflections | l = −64→64 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.052 | w = 1/[σ2(Fo2) + (0.0507P)2 + 1.9226P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.117 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.47 e Å−3 |
9557 reflections | Δρmin = −0.30 e Å−3 |
285 parameters | Absolute structure: Refined as an inversion twin. |
12 restraints | Absolute structure parameter: 0.269 (16) |
Primary atom site location: heavy-atom method |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.000000 | 0.500000 | 0.42152 (2) | 0.04430 (12) | |
S1 | −0.49377 (6) | 0.34309 (6) | 0.35923 (2) | 0.04981 (18) | |
O1 | −0.04873 (18) | 0.38720 (14) | 0.44827 (5) | 0.0582 (5) | |
O2 | −0.0662 (2) | 0.29957 (17) | 0.40738 (6) | 0.0773 (8) | |
N1 | −0.11835 (19) | 0.47507 (17) | 0.39669 (5) | 0.0467 (6) | |
C1 | −0.4884 (2) | 0.4635 (2) | 0.27998 (6) | 0.0473 (6) | |
C2 | −0.4704 (2) | 0.4196 (2) | 0.25269 (6) | 0.0477 (7) | |
C3 | −0.5203 (2) | 0.3174 (2) | 0.24921 (6) | 0.0490 (7) | |
H3 | −0.568683 | 0.275975 | 0.263448 | 0.059* | |
C4 | −0.5005 (3) | 0.2751 (3) | 0.22526 (6) | 0.0610 (8) | |
H4 | −0.536430 | 0.204723 | 0.222687 | 0.073* | |
C5 | −0.4279 (3) | 0.3353 (3) | 0.20479 (8) | 0.0648 (9) | |
H5 | −0.412846 | 0.305765 | 0.188602 | 0.078* | |
C6 | −0.3788 (3) | 0.4355 (3) | 0.20781 (8) | 0.0680 (10) | |
H6 | −0.330349 | 0.476556 | 0.193527 | 0.082* | |
C7 | −0.3995 (2) | 0.4787 (3) | 0.23206 (7) | 0.0584 (8) | |
H7 | −0.364363 | 0.549212 | 0.234341 | 0.070* | |
C8 | −0.4726 (2) | 0.4251 (2) | 0.30859 (6) | 0.0467 (7) | |
C9 | −0.3754 (2) | 0.4551 (2) | 0.31899 (6) | 0.0413 (6) | |
H9 | −0.316802 | 0.497333 | 0.307971 | 0.050* | |
C10 | −0.3733 (2) | 0.4179 (2) | 0.34641 (6) | 0.0450 (6) | |
C11 | −0.5451 (2) | 0.3631 (2) | 0.32797 (7) | 0.0521 (7) | |
C12 | −0.6569 (3) | 0.3122 (3) | 0.32495 (9) | 0.0658 (10) | |
H12A | −0.685942 | 0.240441 | 0.328453 | 0.099* | |
H12B | −0.674123 | 0.323138 | 0.304909 | 0.099* | |
H12C | −0.683416 | 0.339988 | 0.339537 | 0.099* | |
C13 | −0.2862 (2) | 0.4369 (2) | 0.36332 (6) | 0.0428 (6) | |
C14 | −0.1905 (2) | 0.5094 (2) | 0.35477 (6) | 0.0508 (7) | |
H14 | −0.180855 | 0.546818 | 0.337136 | 0.061* | |
C15 | −0.1107 (2) | 0.5265 (2) | 0.37182 (6) | 0.0523 (8) | |
H15 | −0.046249 | 0.577477 | 0.365818 | 0.063* | |
C16 | −0.2099 (2) | 0.4042 (2) | 0.40520 (6) | 0.0494 (7) | |
H16 | −0.216949 | 0.366753 | 0.422635 | 0.059* | |
C17 | −0.2939 (2) | 0.3845 (2) | 0.38938 (6) | 0.0460 (7) | |
H17 | −0.357737 | 0.334681 | 0.396226 | 0.055* | |
C18 | −0.1176 (2) | 0.2144 (2) | 0.45409 (9) | 0.0594 (9) | |
C19 | −0.1554 (3) | 0.1215 (3) | 0.44154 (10) | 0.0708 (10) | |
H19 | −0.151578 | 0.114637 | 0.420705 | 0.085* | |
C20 | −0.1994 (3) | 0.0375 (3) | 0.45973 (10) | 0.0733 (11) | |
H20 | −0.226962 | −0.026818 | 0.450998 | 0.088* | |
C21 | −0.2040 (3) | 0.0454 (2) | 0.49032 (9) | 0.0612 (9) | |
C22 | −0.1669 (3) | 0.1391 (2) | 0.50204 (10) | 0.0792 (12) | |
H22 | −0.170445 | 0.146611 | 0.522858 | 0.095* | |
C23 | −0.1246 (3) | 0.2228 (2) | 0.48412 (9) | 0.0741 (11) | |
H23 | −0.100016 | 0.286973 | 0.492732 | 0.089* | |
C24 | −0.0740 (2) | 0.3061 (2) | 0.43498 (9) | 0.0607 (9) | |
O3 | −0.0874 (11) | 0.7208 (9) | 0.3140 (2) | 0.098 (3) | 0.63 (2) |
H3A | −0.056037 | 0.776391 | 0.323977 | 0.147* | 0.63 (2) |
H3B | −0.069755 | 0.738130 | 0.295704 | 0.147* | 0.63 (2) |
O3A | −0.1463 (15) | 0.6767 (12) | 0.3016 (3) | 0.079 (5) | 0.37 (2) |
H3AA | −0.115899 | 0.655153 | 0.290133 | 0.119* | 0.37 (2) |
H3AB | −0.147414 | 0.726722 | 0.293203 | 0.119* | 0.37 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0495 (3) | 0.0292 (2) | 0.0403 (2) | 0.00922 (19) | 0.000 | 0.000 |
S1 | 0.0507 (4) | 0.0475 (4) | 0.0480 (4) | 0.0222 (4) | 0.0070 (4) | 0.0035 (3) |
O1 | 0.0610 (14) | 0.0340 (10) | 0.0675 (13) | 0.0147 (10) | 0.0045 (11) | 0.0096 (9) |
O2 | 0.0879 (18) | 0.0401 (12) | 0.0904 (19) | 0.0219 (13) | 0.0363 (15) | 0.0151 (12) |
N1 | 0.0513 (14) | 0.0396 (13) | 0.0357 (11) | 0.0126 (11) | 0.0016 (10) | 0.0002 (9) |
C1 | 0.0390 (15) | 0.0513 (16) | 0.0487 (14) | 0.0204 (13) | −0.0006 (12) | −0.0002 (12) |
C2 | 0.0409 (15) | 0.0558 (17) | 0.0491 (15) | 0.0262 (13) | −0.0082 (12) | −0.0057 (13) |
C3 | 0.0471 (17) | 0.0596 (18) | 0.0437 (14) | 0.0293 (15) | −0.0063 (12) | 0.0018 (13) |
C4 | 0.080 (2) | 0.066 (2) | 0.0446 (15) | 0.042 (2) | −0.0205 (18) | −0.0079 (15) |
C5 | 0.078 (2) | 0.081 (3) | 0.0491 (18) | 0.050 (2) | −0.0034 (17) | −0.0064 (17) |
C6 | 0.068 (2) | 0.082 (3) | 0.0553 (19) | 0.039 (2) | 0.0123 (17) | 0.0010 (18) |
C7 | 0.0498 (17) | 0.061 (2) | 0.0566 (17) | 0.0215 (16) | 0.0087 (14) | −0.0016 (15) |
C8 | 0.0533 (18) | 0.0476 (16) | 0.0438 (14) | 0.0287 (14) | 0.0016 (12) | −0.0034 (12) |
C9 | 0.0423 (15) | 0.0450 (15) | 0.0398 (14) | 0.0241 (12) | 0.0034 (11) | −0.0046 (11) |
C10 | 0.0502 (17) | 0.0406 (15) | 0.0411 (14) | 0.0204 (14) | 0.0046 (12) | −0.0043 (11) |
C11 | 0.0542 (17) | 0.0459 (16) | 0.0554 (17) | 0.0243 (14) | 0.0040 (14) | 0.0013 (13) |
C12 | 0.0445 (17) | 0.060 (2) | 0.089 (3) | 0.0228 (16) | 0.0069 (17) | 0.0108 (18) |
C13 | 0.0492 (16) | 0.0369 (13) | 0.0356 (12) | 0.0164 (13) | 0.0021 (12) | −0.0039 (10) |
C14 | 0.0572 (18) | 0.0466 (16) | 0.0350 (12) | 0.0158 (14) | 0.0017 (12) | 0.0050 (13) |
C15 | 0.0429 (16) | 0.0478 (18) | 0.0447 (15) | 0.0066 (13) | 0.0021 (12) | 0.0062 (12) |
C16 | 0.0571 (18) | 0.0423 (15) | 0.0360 (13) | 0.0151 (14) | 0.0019 (12) | 0.0046 (12) |
C17 | 0.0480 (16) | 0.0395 (14) | 0.0387 (14) | 0.0131 (13) | 0.0056 (12) | 0.0042 (11) |
C18 | 0.0517 (18) | 0.0353 (15) | 0.088 (2) | 0.0197 (14) | 0.0134 (16) | 0.0098 (15) |
C19 | 0.072 (2) | 0.0434 (18) | 0.094 (3) | 0.0264 (18) | 0.016 (2) | 0.0085 (18) |
C20 | 0.071 (2) | 0.0342 (16) | 0.101 (3) | 0.0158 (16) | 0.001 (2) | 0.0008 (18) |
C21 | 0.0544 (19) | 0.0332 (15) | 0.094 (3) | 0.0202 (14) | 0.0073 (17) | 0.0086 (16) |
C22 | 0.101 (3) | 0.0439 (17) | 0.087 (3) | 0.031 (2) | 0.011 (2) | 0.0134 (18) |
C23 | 0.096 (3) | 0.0358 (16) | 0.082 (2) | 0.0260 (18) | 0.008 (2) | 0.0104 (15) |
C24 | 0.0513 (18) | 0.0367 (16) | 0.085 (2) | 0.0151 (14) | 0.0140 (16) | 0.0090 (16) |
O3 | 0.131 (8) | 0.102 (5) | 0.061 (4) | 0.058 (6) | 0.028 (5) | 0.005 (4) |
O3A | 0.115 (11) | 0.082 (8) | 0.058 (6) | 0.063 (8) | 0.032 (7) | 0.015 (6) |
Zn1—O1i | 1.9364 (19) | C11—C12 | 1.506 (5) |
Zn1—O1 | 1.9364 (19) | C12—H12A | 0.9800 |
Zn1—N1 | 2.011 (3) | C12—H12B | 0.9800 |
Zn1—N1i | 2.011 (3) | C12—H12C | 0.9800 |
S1—C10 | 1.728 (3) | C13—C14 | 1.391 (4) |
S1—C11 | 1.719 (3) | C13—C17 | 1.398 (4) |
O1—C24 | 1.262 (4) | C14—H14 | 0.9500 |
O2—C24 | 1.259 (4) | C14—C15 | 1.362 (4) |
N1—C15 | 1.345 (4) | C15—H15 | 0.9500 |
N1—C16 | 1.342 (4) | C16—H16 | 0.9500 |
C1—C1ii | 1.345 (6) | C16—C17 | 1.375 (4) |
C1—C2 | 1.496 (4) | C17—H17 | 0.9500 |
C1—C8 | 1.490 (4) | C18—C19 | 1.373 (5) |
C2—C3 | 1.378 (4) | C18—C23 | 1.369 (5) |
C2—C7 | 1.378 (4) | C18—C24 | 1.501 (4) |
C3—H3 | 0.9500 | C19—H19 | 0.9500 |
C3—C4 | 1.373 (4) | C19—C20 | 1.392 (5) |
C4—H4 | 0.9500 | C20—H20 | 0.9500 |
C4—C5 | 1.391 (5) | C20—C21 | 1.389 (5) |
C5—H5 | 0.9500 | C21—C21iii | 1.497 (6) |
C5—C6 | 1.349 (5) | C21—C22 | 1.370 (5) |
C6—H6 | 0.9500 | C22—H22 | 0.9500 |
C6—C7 | 1.399 (5) | C22—C23 | 1.382 (5) |
C7—H7 | 0.9500 | C23—H23 | 0.9500 |
C8—C9 | 1.413 (4) | O3—H3A | 0.8706 |
C8—C11 | 1.365 (4) | O3—H3B | 0.8693 |
C9—H9 | 0.9500 | O3A—H3AA | 0.8701 |
C9—C10 | 1.370 (4) | O3A—H3AB | 0.8699 |
C10—C13 | 1.445 (4) | ||
O1i—Zn1—O1 | 103.00 (13) | C11—C12—H12A | 109.5 |
O1—Zn1—N1 | 105.46 (10) | C11—C12—H12B | 109.5 |
O1i—Zn1—N1i | 105.46 (10) | C11—C12—H12C | 109.5 |
O1i—Zn1—N1 | 115.21 (10) | H12A—C12—H12B | 109.5 |
O1—Zn1—N1i | 115.21 (10) | H12A—C12—H12C | 109.5 |
N1—Zn1—N1i | 112.41 (13) | H12B—C12—H12C | 109.5 |
C11—S1—C10 | 92.60 (15) | C14—C13—C10 | 121.7 (3) |
C24—O1—Zn1 | 112.8 (2) | C14—C13—C17 | 116.6 (3) |
C15—N1—Zn1 | 123.2 (2) | C17—C13—C10 | 121.6 (3) |
C16—N1—Zn1 | 119.04 (19) | C13—C14—H14 | 120.2 |
C16—N1—C15 | 117.7 (3) | C15—C14—C13 | 119.7 (3) |
C1ii—C1—C2 | 124.66 (16) | C15—C14—H14 | 120.2 |
C1ii—C1—C8 | 120.01 (15) | N1—C15—C14 | 123.5 (3) |
C8—C1—C2 | 115.2 (2) | N1—C15—H15 | 118.3 |
C3—C2—C1 | 119.3 (3) | C14—C15—H15 | 118.3 |
C7—C2—C1 | 121.4 (3) | N1—C16—H16 | 119.1 |
C7—C2—C3 | 119.2 (3) | N1—C16—C17 | 121.8 (3) |
C2—C3—H3 | 119.8 | C17—C16—H16 | 119.1 |
C4—C3—C2 | 120.4 (3) | C13—C17—H17 | 119.7 |
C4—C3—H3 | 119.8 | C16—C17—C13 | 120.6 (3) |
C3—C4—H4 | 120.0 | C16—C17—H17 | 119.7 |
C3—C4—C5 | 120.0 (3) | C19—C18—C24 | 120.5 (3) |
C5—C4—H4 | 120.0 | C23—C18—C19 | 119.7 (3) |
C4—C5—H5 | 119.8 | C23—C18—C24 | 119.8 (3) |
C6—C5—C4 | 120.3 (3) | C18—C19—H19 | 120.4 |
C6—C5—H5 | 119.8 | C18—C19—C20 | 119.2 (4) |
C5—C6—H6 | 120.2 | C20—C19—H19 | 120.4 |
C5—C6—C7 | 119.7 (4) | C19—C20—H20 | 119.2 |
C7—C6—H6 | 120.2 | C21—C20—C19 | 121.7 (3) |
C2—C7—C6 | 120.5 (3) | C21—C20—H20 | 119.2 |
C2—C7—H7 | 119.8 | C20—C21—C21iii | 121.1 (4) |
C6—C7—H7 | 119.8 | C22—C21—C20 | 117.6 (3) |
C9—C8—C1 | 121.0 (3) | C22—C21—C21iii | 121.3 (4) |
C11—C8—C1 | 126.4 (3) | C21—C22—H22 | 119.4 |
C11—C8—C9 | 112.5 (3) | C21—C22—C23 | 121.1 (4) |
C8—C9—H9 | 123.0 | C23—C22—H22 | 119.4 |
C10—C9—C8 | 113.9 (3) | C18—C23—C22 | 120.7 (3) |
C10—C9—H9 | 123.0 | C18—C23—H23 | 119.6 |
C9—C10—S1 | 109.8 (2) | C22—C23—H23 | 119.6 |
C9—C10—C13 | 127.3 (3) | O1—C24—C18 | 115.9 (3) |
C13—C10—S1 | 122.9 (2) | O2—C24—O1 | 123.6 (3) |
C8—C11—S1 | 111.1 (2) | O2—C24—C18 | 120.4 (3) |
C8—C11—C12 | 129.3 (3) | H3A—O3—H3B | 104.5 |
C12—C11—S1 | 119.5 (2) | H3AA—O3A—H3AB | 109.6 |
Zn1—O1—C24—O2 | 1.6 (5) | C9—C8—C11—C12 | −177.8 (3) |
Zn1—O1—C24—C18 | −177.0 (2) | C9—C10—C13—C14 | 9.4 (5) |
Zn1—N1—C15—C14 | 179.4 (2) | C9—C10—C13—C17 | −171.7 (3) |
Zn1—N1—C16—C17 | 179.2 (2) | C10—S1—C11—C8 | −0.3 (2) |
S1—C10—C13—C14 | −169.6 (2) | C10—S1—C11—C12 | 178.5 (3) |
S1—C10—C13—C17 | 9.3 (4) | C10—C13—C14—C15 | 178.3 (3) |
N1—C16—C17—C13 | 1.2 (5) | C10—C13—C17—C16 | −179.6 (3) |
C1ii—C1—C2—C3 | −129.2 (4) | C11—S1—C10—C9 | −0.3 (2) |
C1ii—C1—C2—C7 | 55.9 (5) | C11—S1—C10—C13 | 178.8 (3) |
C1ii—C1—C8—C9 | −101.9 (4) | C11—C8—C9—C10 | −1.2 (4) |
C1ii—C1—C8—C11 | 75.3 (5) | C13—C14—C15—N1 | 1.5 (5) |
C1—C2—C3—C4 | −176.0 (3) | C14—C13—C17—C16 | −0.6 (4) |
C1—C2—C7—C6 | 175.4 (3) | C15—N1—C16—C17 | −0.4 (4) |
C1—C8—C9—C10 | 176.4 (3) | C16—N1—C15—C14 | −1.0 (5) |
C1—C8—C11—S1 | −176.5 (2) | C17—C13—C14—C15 | −0.6 (4) |
C1—C8—C11—C12 | 4.8 (5) | C18—C19—C20—C21 | −1.5 (6) |
C2—C1—C8—C9 | 74.6 (3) | C19—C18—C23—C22 | 1.7 (6) |
C2—C1—C8—C11 | −108.2 (3) | C19—C18—C24—O1 | 174.4 (3) |
C2—C3—C4—C5 | 1.7 (5) | C19—C18—C24—O2 | −4.2 (5) |
C3—C2—C7—C6 | 0.4 (5) | C19—C20—C21—C21iii | −178.6 (3) |
C3—C4—C5—C6 | −2.0 (5) | C19—C20—C21—C22 | 2.5 (6) |
C4—C5—C6—C7 | 1.5 (6) | C20—C21—C22—C23 | −1.4 (6) |
C5—C6—C7—C2 | −0.7 (5) | C21iii—C21—C22—C23 | 179.6 (3) |
C7—C2—C3—C4 | −0.9 (4) | C21—C22—C23—C18 | −0.7 (7) |
C8—C1—C2—C3 | 54.5 (4) | C23—C18—C19—C20 | −0.6 (6) |
C8—C1—C2—C7 | −120.4 (3) | C23—C18—C24—O1 | −2.1 (5) |
C8—C9—C10—S1 | 0.9 (3) | C23—C18—C24—O2 | 179.3 (4) |
C8—C9—C10—C13 | −178.2 (3) | C24—C18—C19—C20 | −177.1 (4) |
C9—C8—C11—S1 | 0.9 (3) | C24—C18—C23—C22 | 178.2 (4) |
Symmetry codes: (i) −x, −y+1, z; (ii) −x−1, −y+1, z; (iii) x−y, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3A—H3AA···O2iv | 0.87 | 1.70 | 2.534 (10) | 161 |
Symmetry code: (iv) x, x−y+1, −z+2/3. |
C76H56N4O4S4Zn2 | F(000) = 2784 |
Mr = 1348.22 | Dx = 1.119 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 20.2935 (7) Å | Cell parameters from 9980 reflections |
b = 16.6798 (6) Å | θ = 2.2–23.5° |
c = 25.1409 (12) Å | µ = 0.75 mm−1 |
β = 109.835 (1)° | T = 273 K |
V = 8005.1 (6) Å3 | Prism, colourless |
Z = 4 | 0.1 × 0.06 × 0.02 mm |
Bruker APEX-II CCD diffractometer | 6734 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.057 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1392 before and 0.0646 after correction. The Ratio of minimum to maximum transmission is 0.9153. The λ/2 correction factor is Not present. | θmax = 26.4°, θmin = 1.6° |
Tmin = 0.683, Tmax = 0.746 | h = −25→25 |
70213 measured reflections | k = −20→20 |
8196 independent reflections | l = −31→31 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0355P)2 + 7.8545P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
8196 reflections | Δρmax = 0.46 e Å−3 |
408 parameters | Δρmin = −0.32 e Å−3 |
0 restraints |
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 | ||
Zn1 | 0.39950 (2) | 0.30479 (2) | 0.43045 (2) | 0.02688 (7) | |
S1 | 0.53728 (3) | 0.42156 (3) | 0.72837 (2) | 0.03357 (12) | |
S2 | 0.54488 (3) | 0.74442 (3) | 0.73354 (2) | 0.04009 (14) | |
O1 | 0.43943 (8) | 0.19779 (8) | 0.44251 (6) | 0.0344 (3) | |
O2 | 0.38469 (7) | 0.16820 (8) | 0.50381 (6) | 0.0332 (3) | |
N1 | 0.41923 (9) | 0.35329 (10) | 0.50764 (7) | 0.0304 (4) | |
N2 | 0.79361 (8) | 0.79926 (9) | 0.89446 (6) | 0.0259 (3) | |
C1 | 0.40354 (10) | 0.54698 (12) | 0.78255 (7) | 0.0264 (4) | |
C2 | 0.34292 (10) | 0.50291 (11) | 0.78975 (7) | 0.0255 (4) | |
C3 | 0.35271 (10) | 0.43670 (12) | 0.82466 (8) | 0.0301 (4) | |
H3 | 0.397852 | 0.419456 | 0.844942 | 0.036* | |
C4 | 0.29557 (12) | 0.39591 (13) | 0.82956 (9) | 0.0377 (5) | |
H4 | 0.302641 | 0.352458 | 0.854046 | 0.045* | |
C5 | 0.22844 (11) | 0.41915 (13) | 0.79851 (10) | 0.0397 (5) | |
H5 | 0.190248 | 0.391478 | 0.801857 | 0.048* | |
C6 | 0.21831 (11) | 0.48323 (15) | 0.76272 (11) | 0.0467 (6) | |
H6 | 0.173115 | 0.498667 | 0.741073 | 0.056* | |
C7 | 0.27550 (11) | 0.52531 (14) | 0.75867 (10) | 0.0428 (5) | |
H7 | 0.268146 | 0.569278 | 0.734601 | 0.051* | |
C8 | 0.44326 (10) | 0.50050 (12) | 0.75283 (8) | 0.0278 (4) | |
C9 | 0.41271 (10) | 0.47672 (12) | 0.69541 (8) | 0.0276 (4) | |
H9 | 0.366727 | 0.488584 | 0.673463 | 0.033* | |
C10 | 0.45708 (10) | 0.43497 (12) | 0.67558 (8) | 0.0278 (4) | |
C11 | 0.51098 (10) | 0.47478 (13) | 0.77676 (8) | 0.0307 (4) | |
C12 | 0.56039 (11) | 0.48518 (15) | 0.83599 (8) | 0.0388 (5) | |
H12A | 0.598584 | 0.519032 | 0.835825 | 0.058* | |
H12B | 0.578213 | 0.433798 | 0.851486 | 0.058* | |
H12C | 0.536081 | 0.509390 | 0.858642 | 0.058* | |
C13 | 0.44426 (10) | 0.40581 (12) | 0.61817 (8) | 0.0275 (4) | |
C14 | 0.38362 (13) | 0.42552 (16) | 0.57444 (9) | 0.0500 (7) | |
H14 | 0.349612 | 0.456977 | 0.581438 | 0.060* | |
C15 | 0.37374 (12) | 0.39862 (15) | 0.52082 (9) | 0.0465 (6) | |
H15 | 0.332706 | 0.413105 | 0.492105 | 0.056* | |
C16 | 0.47704 (12) | 0.33279 (17) | 0.54992 (10) | 0.0535 (7) | |
H16 | 0.509330 | 0.299614 | 0.541952 | 0.064* | |
C17 | 0.49127 (11) | 0.35809 (15) | 0.60446 (10) | 0.0465 (6) | |
H17 | 0.532858 | 0.342934 | 0.632284 | 0.056* | |
C18 | 0.41832 (10) | 0.62348 (12) | 0.79829 (8) | 0.0297 (4) | |
C19 | 0.38209 (10) | 0.66856 (12) | 0.83175 (9) | 0.0330 (4) | |
C20 | 0.34621 (12) | 0.73895 (14) | 0.81157 (11) | 0.0494 (6) | |
H20 | 0.344958 | 0.759403 | 0.776833 | 0.059* | |
C21 | 0.31180 (15) | 0.77942 (17) | 0.84334 (14) | 0.0662 (8) | |
H21 | 0.286544 | 0.825777 | 0.829021 | 0.079* | |
C22 | 0.31504 (17) | 0.75126 (19) | 0.89534 (14) | 0.0738 (9) | |
H22 | 0.291945 | 0.778299 | 0.916195 | 0.089* | |
C23 | 0.35246 (17) | 0.68301 (19) | 0.91654 (12) | 0.0695 (9) | |
H23 | 0.355828 | 0.664787 | 0.952331 | 0.083* | |
C24 | 0.38519 (13) | 0.64119 (15) | 0.88513 (9) | 0.0479 (6) | |
H24 | 0.409526 | 0.594351 | 0.899609 | 0.057* | |
C25 | 0.47395 (11) | 0.66908 (12) | 0.78486 (8) | 0.0319 (4) | |
C26 | 0.53750 (10) | 0.69243 (11) | 0.82694 (8) | 0.0263 (4) | |
H26 | 0.548086 | 0.680978 | 0.865141 | 0.032* | |
C27 | 0.58185 (10) | 0.73350 (11) | 0.80602 (8) | 0.0259 (4) | |
C28 | 0.46988 (12) | 0.69453 (14) | 0.73168 (9) | 0.0423 (6) | |
C29 | 0.41018 (16) | 0.68577 (19) | 0.67688 (10) | 0.0712 (10) | |
H29A | 0.426302 | 0.659035 | 0.649774 | 0.107* | |
H29B | 0.392554 | 0.737850 | 0.662834 | 0.107* | |
H29C | 0.373511 | 0.654813 | 0.682998 | 0.107* | |
C30 | 0.65295 (10) | 0.76085 (10) | 0.83683 (7) | 0.0239 (4) | |
C31 | 0.68531 (10) | 0.74174 (11) | 0.89392 (8) | 0.0270 (4) | |
H31 | 0.660161 | 0.716285 | 0.913838 | 0.032* | |
C32 | 0.75464 (10) | 0.76092 (12) | 0.92037 (8) | 0.0280 (4) | |
H32 | 0.775680 | 0.746646 | 0.958128 | 0.034* | |
C33 | 0.76135 (10) | 0.82177 (11) | 0.84025 (8) | 0.0287 (4) | |
H33 | 0.786681 | 0.850802 | 0.822138 | 0.034* | |
C34 | 0.69274 (10) | 0.80357 (11) | 0.81080 (8) | 0.0279 (4) | |
H34 | 0.672646 | 0.819759 | 0.773358 | 0.033* | |
C35 | 0.46417 (10) | 0.07315 (11) | 0.48917 (7) | 0.0259 (4) | |
C36 | 0.44610 (10) | 0.01389 (12) | 0.52081 (7) | 0.0279 (4) | |
H36 | 0.409793 | 0.023110 | 0.534767 | 0.033* | |
C37 | 0.51857 (10) | 0.05835 (12) | 0.46829 (8) | 0.0278 (4) | |
H37 | 0.531063 | 0.097261 | 0.446967 | 0.033* | |
C38 | 0.42563 (10) | 0.15179 (12) | 0.47843 (8) | 0.0284 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.02694 (12) | 0.03112 (13) | 0.02560 (12) | −0.00254 (9) | 0.01287 (9) | −0.00064 (9) |
S1 | 0.0243 (2) | 0.0539 (3) | 0.0228 (2) | −0.0014 (2) | 0.00844 (19) | 0.0048 (2) |
S2 | 0.0492 (3) | 0.0458 (3) | 0.0205 (2) | −0.0213 (3) | 0.0057 (2) | 0.0040 (2) |
O1 | 0.0419 (8) | 0.0352 (8) | 0.0308 (7) | 0.0046 (6) | 0.0187 (6) | 0.0024 (6) |
O2 | 0.0318 (8) | 0.0386 (8) | 0.0327 (8) | 0.0034 (6) | 0.0154 (6) | −0.0018 (6) |
N1 | 0.0306 (9) | 0.0323 (9) | 0.0299 (9) | −0.0030 (7) | 0.0123 (7) | −0.0033 (7) |
N2 | 0.0309 (8) | 0.0261 (8) | 0.0220 (8) | −0.0023 (7) | 0.0106 (7) | −0.0011 (6) |
C1 | 0.0235 (9) | 0.0357 (11) | 0.0176 (9) | −0.0041 (8) | 0.0037 (7) | 0.0045 (7) |
C2 | 0.0263 (10) | 0.0317 (10) | 0.0189 (9) | −0.0038 (8) | 0.0083 (7) | −0.0003 (7) |
C3 | 0.0296 (10) | 0.0321 (10) | 0.0278 (10) | 0.0014 (8) | 0.0088 (8) | 0.0031 (8) |
C4 | 0.0442 (13) | 0.0345 (11) | 0.0402 (12) | −0.0032 (9) | 0.0219 (10) | 0.0075 (9) |
C5 | 0.0341 (11) | 0.0426 (13) | 0.0513 (14) | −0.0059 (10) | 0.0259 (10) | 0.0004 (10) |
C6 | 0.0249 (11) | 0.0529 (14) | 0.0621 (16) | 0.0046 (10) | 0.0144 (11) | 0.0122 (12) |
C7 | 0.0306 (11) | 0.0434 (13) | 0.0509 (14) | 0.0009 (10) | 0.0094 (10) | 0.0222 (11) |
C8 | 0.0253 (9) | 0.0357 (11) | 0.0231 (9) | −0.0096 (8) | 0.0091 (8) | 0.0029 (8) |
C9 | 0.0229 (9) | 0.0368 (11) | 0.0225 (9) | −0.0091 (8) | 0.0069 (8) | 0.0019 (8) |
C10 | 0.0227 (9) | 0.0380 (11) | 0.0220 (9) | −0.0065 (8) | 0.0067 (8) | 0.0040 (8) |
C11 | 0.0270 (10) | 0.0424 (12) | 0.0236 (9) | −0.0086 (8) | 0.0099 (8) | 0.0033 (8) |
C12 | 0.0309 (11) | 0.0610 (15) | 0.0225 (10) | −0.0033 (10) | 0.0066 (8) | 0.0038 (10) |
C13 | 0.0262 (10) | 0.0320 (10) | 0.0255 (10) | −0.0053 (8) | 0.0102 (8) | 0.0023 (8) |
C14 | 0.0443 (13) | 0.0803 (18) | 0.0240 (11) | 0.0296 (13) | 0.0098 (10) | −0.0020 (11) |
C15 | 0.0438 (13) | 0.0671 (16) | 0.0251 (11) | 0.0242 (12) | 0.0073 (10) | 0.0010 (10) |
C16 | 0.0284 (12) | 0.0715 (17) | 0.0495 (14) | 0.0117 (11) | −0.0013 (10) | −0.0336 (13) |
C17 | 0.0287 (11) | 0.0554 (15) | 0.0424 (13) | 0.0088 (10) | −0.0049 (10) | −0.0181 (11) |
C18 | 0.0279 (10) | 0.0349 (11) | 0.0218 (9) | −0.0037 (8) | 0.0024 (8) | 0.0066 (8) |
C19 | 0.0285 (10) | 0.0325 (11) | 0.0315 (11) | −0.0019 (8) | 0.0016 (8) | −0.0007 (9) |
C20 | 0.0439 (14) | 0.0451 (14) | 0.0512 (15) | 0.0052 (11) | 0.0058 (11) | 0.0136 (11) |
C21 | 0.0581 (17) | 0.0505 (16) | 0.079 (2) | 0.0284 (14) | 0.0092 (15) | 0.0032 (15) |
C22 | 0.079 (2) | 0.076 (2) | 0.065 (2) | 0.0375 (17) | 0.0242 (17) | −0.0046 (16) |
C23 | 0.090 (2) | 0.077 (2) | 0.0421 (15) | 0.0419 (17) | 0.0231 (15) | 0.0034 (14) |
C24 | 0.0603 (16) | 0.0489 (14) | 0.0326 (12) | 0.0218 (12) | 0.0132 (11) | 0.0028 (10) |
C25 | 0.0347 (11) | 0.0315 (10) | 0.0271 (10) | −0.0066 (8) | 0.0076 (9) | 0.0032 (8) |
C26 | 0.0304 (10) | 0.0264 (9) | 0.0213 (9) | −0.0011 (8) | 0.0075 (8) | 0.0011 (7) |
C27 | 0.0324 (10) | 0.0247 (9) | 0.0212 (9) | −0.0012 (8) | 0.0099 (8) | 0.0000 (7) |
C28 | 0.0461 (13) | 0.0465 (13) | 0.0267 (11) | −0.0219 (11) | 0.0025 (10) | 0.0059 (9) |
C29 | 0.0737 (19) | 0.091 (2) | 0.0285 (13) | −0.0467 (17) | −0.0098 (12) | 0.0180 (13) |
C30 | 0.0285 (10) | 0.0214 (9) | 0.0222 (9) | −0.0002 (7) | 0.0093 (8) | −0.0023 (7) |
C31 | 0.0304 (10) | 0.0326 (10) | 0.0219 (9) | −0.0017 (8) | 0.0140 (8) | 0.0008 (8) |
C32 | 0.0311 (10) | 0.0347 (11) | 0.0193 (9) | −0.0009 (8) | 0.0102 (8) | −0.0014 (8) |
C33 | 0.0338 (11) | 0.0258 (10) | 0.0289 (10) | −0.0039 (8) | 0.0136 (9) | 0.0029 (8) |
C34 | 0.0358 (11) | 0.0246 (9) | 0.0226 (9) | −0.0011 (8) | 0.0091 (8) | 0.0035 (7) |
C35 | 0.0249 (9) | 0.0339 (10) | 0.0168 (9) | −0.0022 (8) | 0.0042 (7) | −0.0058 (7) |
C36 | 0.0235 (9) | 0.0405 (11) | 0.0202 (9) | −0.0005 (8) | 0.0081 (7) | −0.0047 (8) |
C37 | 0.0275 (10) | 0.0354 (10) | 0.0202 (9) | −0.0033 (8) | 0.0076 (8) | −0.0015 (8) |
C38 | 0.0270 (10) | 0.0348 (11) | 0.0215 (9) | −0.0027 (8) | 0.0056 (8) | −0.0068 (8) |
Zn1—O1 | 1.9409 (14) | C15—H15 | 0.9300 |
Zn1—N1 | 2.0134 (16) | C16—H16 | 0.9300 |
Zn1—N2i | 2.0311 (16) | C16—C17 | 1.368 (3) |
S1—C10 | 1.7304 (19) | C17—H17 | 0.9300 |
S1—C11 | 1.730 (2) | C18—C19 | 1.495 (3) |
S2—C27 | 1.7288 (19) | C18—C25 | 1.492 (3) |
S2—C28 | 1.721 (2) | C19—C20 | 1.384 (3) |
O1—C38 | 1.286 (2) | C19—C24 | 1.398 (3) |
O2—C38 | 1.238 (2) | C20—H20 | 0.9300 |
N1—C15 | 1.319 (3) | C20—C21 | 1.400 (4) |
N1—C16 | 1.333 (3) | C21—H21 | 0.9300 |
N2—C32 | 1.345 (2) | C21—C22 | 1.370 (4) |
N2—C33 | 1.350 (2) | C22—H22 | 0.9300 |
C1—C2 | 1.496 (2) | C22—C23 | 1.372 (4) |
C1—C8 | 1.489 (3) | C23—H23 | 0.9300 |
C1—C18 | 1.339 (3) | C23—C24 | 1.381 (3) |
C2—C3 | 1.382 (3) | C24—H24 | 0.9300 |
C2—C7 | 1.377 (3) | C25—C26 | 1.417 (3) |
C3—H3 | 0.9300 | C25—C28 | 1.378 (3) |
C3—C4 | 1.386 (3) | C26—H26 | 0.9300 |
C4—H4 | 0.9300 | C26—C27 | 1.370 (3) |
C4—C5 | 1.376 (3) | C27—C30 | 1.460 (3) |
C5—H5 | 0.9300 | C28—C29 | 1.502 (3) |
C5—C6 | 1.367 (3) | C29—H29A | 0.9600 |
C6—H6 | 0.9300 | C29—H29B | 0.9600 |
C6—C7 | 1.389 (3) | C29—H29C | 0.9600 |
C7—H7 | 0.9300 | C30—C31 | 1.398 (3) |
C8—C9 | 1.421 (3) | C30—C34 | 1.395 (3) |
C8—C11 | 1.369 (3) | C31—H31 | 0.9300 |
C9—H9 | 0.9300 | C31—C32 | 1.374 (3) |
C9—C10 | 1.360 (3) | C32—H32 | 0.9300 |
C10—C13 | 1.460 (3) | C33—H33 | 0.9300 |
C11—C12 | 1.496 (3) | C33—C34 | 1.371 (3) |
C12—H12A | 0.9600 | C34—H34 | 0.9300 |
C12—H12B | 0.9600 | C35—C36 | 1.394 (3) |
C12—H12C | 0.9600 | C35—C37 | 1.396 (3) |
C13—C14 | 1.383 (3) | C35—C38 | 1.504 (3) |
C13—C17 | 1.373 (3) | C36—H36 | 0.9300 |
C14—H14 | 0.9300 | C36—C37ii | 1.381 (3) |
C14—C15 | 1.370 (3) | C37—H37 | 0.9300 |
O1—Zn1—N1 | 106.44 (6) | C1—C18—C19 | 122.82 (18) |
O1—Zn1—N2i | 110.51 (6) | C1—C18—C25 | 121.97 (19) |
N1—Zn1—N2i | 106.37 (6) | C25—C18—C19 | 115.18 (17) |
C11—S1—C10 | 92.22 (9) | C20—C19—C18 | 121.2 (2) |
C28—S2—C27 | 92.36 (10) | C20—C19—C24 | 118.4 (2) |
C38—O1—Zn1 | 118.64 (12) | C24—C19—C18 | 120.35 (18) |
C15—N1—Zn1 | 123.03 (14) | C19—C20—H20 | 119.9 |
C15—N1—C16 | 116.63 (18) | C19—C20—C21 | 120.1 (2) |
C16—N1—Zn1 | 119.92 (14) | C21—C20—H20 | 119.9 |
C32—N2—Zn1iii | 120.86 (13) | C20—C21—H21 | 119.8 |
C32—N2—C33 | 117.25 (17) | C22—C21—C20 | 120.5 (2) |
C33—N2—Zn1iii | 120.97 (13) | C22—C21—H21 | 119.8 |
C8—C1—C2 | 114.35 (16) | C21—C22—H22 | 120.1 |
C18—C1—C2 | 122.90 (18) | C21—C22—C23 | 119.8 (3) |
C18—C1—C8 | 122.62 (17) | C23—C22—H22 | 120.1 |
C3—C2—C1 | 121.50 (17) | C22—C23—H23 | 119.8 |
C7—C2—C1 | 119.83 (17) | C22—C23—C24 | 120.5 (3) |
C7—C2—C3 | 118.57 (18) | C24—C23—H23 | 119.8 |
C2—C3—H3 | 119.9 | C19—C24—H24 | 119.7 |
C2—C3—C4 | 120.29 (19) | C23—C24—C19 | 120.7 (2) |
C4—C3—H3 | 119.9 | C23—C24—H24 | 119.7 |
C3—C4—H4 | 119.7 | C26—C25—C18 | 122.54 (17) |
C5—C4—C3 | 120.6 (2) | C28—C25—C18 | 125.15 (18) |
C5—C4—H4 | 119.7 | C28—C25—C26 | 112.29 (18) |
C4—C5—H5 | 120.3 | C25—C26—H26 | 123.2 |
C6—C5—C4 | 119.5 (2) | C27—C26—C25 | 113.62 (17) |
C6—C5—H5 | 120.3 | C27—C26—H26 | 123.2 |
C5—C6—H6 | 120.0 | C26—C27—S2 | 110.52 (14) |
C5—C6—C7 | 120.0 (2) | C26—C27—C30 | 127.75 (17) |
C7—C6—H6 | 120.0 | C30—C27—S2 | 121.58 (13) |
C2—C7—C6 | 121.0 (2) | C25—C28—S2 | 111.18 (16) |
C2—C7—H7 | 119.5 | C25—C28—C29 | 128.6 (2) |
C6—C7—H7 | 119.5 | C29—C28—S2 | 120.18 (17) |
C9—C8—C1 | 122.09 (17) | C28—C29—H29A | 109.5 |
C11—C8—C1 | 125.18 (17) | C28—C29—H29B | 109.5 |
C11—C8—C9 | 112.72 (18) | C28—C29—H29C | 109.5 |
C8—C9—H9 | 123.2 | H29A—C29—H29B | 109.5 |
C10—C9—C8 | 113.61 (17) | H29A—C29—H29C | 109.5 |
C10—C9—H9 | 123.2 | H29B—C29—H29C | 109.5 |
C9—C10—S1 | 110.64 (14) | C31—C30—C27 | 120.60 (16) |
C9—C10—C13 | 127.94 (17) | C34—C30—C27 | 122.39 (16) |
C13—C10—S1 | 121.39 (15) | C34—C30—C31 | 116.94 (17) |
C8—C11—S1 | 110.78 (14) | C30—C31—H31 | 120.3 |
C8—C11—C12 | 129.42 (19) | C32—C31—C30 | 119.40 (17) |
C12—C11—S1 | 119.78 (15) | C32—C31—H31 | 120.3 |
C11—C12—H12A | 109.5 | N2—C32—C31 | 123.37 (17) |
C11—C12—H12B | 109.5 | N2—C32—H32 | 118.3 |
C11—C12—H12C | 109.5 | C31—C32—H32 | 118.3 |
H12A—C12—H12B | 109.5 | N2—C33—H33 | 118.7 |
H12A—C12—H12C | 109.5 | N2—C33—C34 | 122.65 (17) |
H12B—C12—H12C | 109.5 | C34—C33—H33 | 118.7 |
C14—C13—C10 | 121.23 (18) | C30—C34—H34 | 119.9 |
C17—C13—C10 | 122.35 (18) | C33—C34—C30 | 120.21 (17) |
C17—C13—C14 | 116.41 (19) | C33—C34—H34 | 119.9 |
C13—C14—H14 | 120.1 | C36—C35—C37 | 118.96 (18) |
C15—C14—C13 | 119.9 (2) | C36—C35—C38 | 119.97 (17) |
C15—C14—H14 | 120.1 | C37—C35—C38 | 121.06 (17) |
N1—C15—C14 | 123.6 (2) | C35—C36—H36 | 119.6 |
N1—C15—H15 | 118.2 | C37ii—C36—C35 | 120.83 (17) |
C14—C15—H15 | 118.2 | C37ii—C36—H36 | 119.6 |
N1—C16—H16 | 118.3 | C35—C37—H37 | 119.9 |
N1—C16—C17 | 123.3 (2) | C36ii—C37—C35 | 120.20 (18) |
C17—C16—H16 | 118.3 | C36ii—C37—H37 | 119.9 |
C13—C17—H17 | 119.9 | O1—C38—C35 | 115.00 (16) |
C16—C17—C13 | 120.1 (2) | O2—C38—O1 | 125.04 (19) |
C16—C17—H17 | 119.9 | O2—C38—C35 | 119.96 (17) |
Zn1—O1—C38—O2 | 5.0 (3) | C14—C13—C17—C16 | 0.2 (4) |
Zn1—O1—C38—C35 | −174.39 (12) | C15—N1—C16—C17 | −1.8 (4) |
Zn1—N1—C15—C14 | 173.4 (2) | C16—N1—C15—C14 | 0.8 (4) |
Zn1—N1—C16—C17 | −174.6 (2) | C17—C13—C14—C15 | −1.0 (4) |
Zn1iii—N2—C32—C31 | −167.00 (15) | C18—C1—C2—C3 | −116.6 (2) |
Zn1iii—N2—C33—C34 | 165.89 (15) | C18—C1—C2—C7 | 67.3 (3) |
S1—C10—C13—C14 | −171.49 (18) | C18—C1—C8—C9 | −111.1 (2) |
S1—C10—C13—C17 | 8.2 (3) | C18—C1—C8—C11 | 70.2 (3) |
S2—C27—C30—C31 | −171.16 (14) | C18—C19—C20—C21 | 179.0 (2) |
S2—C27—C30—C34 | 5.9 (3) | C18—C19—C24—C23 | 179.3 (2) |
N1—C16—C17—C13 | 1.3 (4) | C18—C25—C26—C27 | 179.74 (18) |
N2—C33—C34—C30 | 0.7 (3) | C18—C25—C28—S2 | −179.51 (17) |
C1—C2—C3—C4 | −178.54 (18) | C18—C25—C28—C29 | 2.4 (4) |
C1—C2—C7—C6 | 177.2 (2) | C19—C18—C25—C26 | 67.6 (3) |
C1—C8—C9—C10 | 179.83 (17) | C19—C18—C25—C28 | −111.2 (2) |
C1—C8—C11—S1 | 179.07 (15) | C19—C20—C21—C22 | 2.0 (4) |
C1—C8—C11—C12 | 0.6 (3) | C20—C19—C24—C23 | 0.8 (4) |
C1—C18—C19—C20 | −122.1 (2) | C20—C21—C22—C23 | 0.2 (5) |
C1—C18—C19—C24 | 59.4 (3) | C21—C22—C23—C24 | −1.9 (5) |
C1—C18—C25—C26 | −110.8 (2) | C22—C23—C24—C19 | 1.4 (5) |
C1—C18—C25—C28 | 70.5 (3) | C24—C19—C20—C21 | −2.5 (4) |
C2—C1—C8—C9 | 65.0 (2) | C25—C18—C19—C20 | 59.6 (3) |
C2—C1—C8—C11 | −113.7 (2) | C25—C18—C19—C24 | −118.9 (2) |
C2—C1—C18—C19 | 8.8 (3) | C25—C26—C27—S2 | 0.5 (2) |
C2—C1—C18—C25 | −172.95 (17) | C25—C26—C27—C30 | −175.14 (18) |
C2—C3—C4—C5 | 2.0 (3) | C26—C25—C28—S2 | 1.6 (3) |
C3—C2—C7—C6 | 0.9 (3) | C26—C25—C28—C29 | −176.5 (3) |
C3—C4—C5—C6 | −0.2 (3) | C26—C27—C30—C31 | 4.0 (3) |
C4—C5—C6—C7 | −1.2 (4) | C26—C27—C30—C34 | −178.91 (19) |
C5—C6—C7—C2 | 0.9 (4) | C27—S2—C28—C25 | −1.17 (19) |
C7—C2—C3—C4 | −2.3 (3) | C27—S2—C28—C29 | 177.1 (2) |
C8—C1—C2—C3 | 67.4 (2) | C27—C30—C31—C32 | 173.22 (17) |
C8—C1—C2—C7 | −108.8 (2) | C27—C30—C34—C33 | −174.19 (18) |
C8—C1—C18—C19 | −175.48 (17) | C28—S2—C27—C26 | 0.41 (16) |
C8—C1—C18—C25 | 2.8 (3) | C28—S2—C27—C30 | 176.32 (17) |
C8—C9—C10—S1 | 1.7 (2) | C28—C25—C26—C27 | −1.4 (3) |
C8—C9—C10—C13 | −176.15 (18) | C30—C31—C32—N2 | 1.5 (3) |
C9—C8—C11—S1 | 0.3 (2) | C31—C30—C34—C33 | 3.0 (3) |
C9—C8—C11—C12 | −178.2 (2) | C32—N2—C33—C34 | −3.3 (3) |
C9—C10—C13—C14 | 6.2 (3) | C33—N2—C32—C31 | 2.2 (3) |
C9—C10—C13—C17 | −174.2 (2) | C34—C30—C31—C32 | −4.0 (3) |
C10—S1—C11—C8 | 0.60 (16) | C36—C35—C37—C36ii | −0.3 (3) |
C10—S1—C11—C12 | 179.27 (17) | C36—C35—C38—O1 | −170.75 (17) |
C10—C13—C14—C15 | 178.6 (2) | C36—C35—C38—O2 | 9.8 (3) |
C10—C13—C17—C16 | −179.5 (2) | C37—C35—C36—C37ii | 0.3 (3) |
C11—S1—C10—C9 | −1.34 (15) | C37—C35—C38—O1 | 9.8 (3) |
C11—S1—C10—C13 | 176.71 (16) | C37—C35—C38—O2 | −169.69 (17) |
C11—C8—C9—C10 | −1.3 (2) | C38—C35—C36—C37ii | −179.22 (16) |
C13—C14—C15—N1 | 0.6 (4) | C38—C35—C37—C36ii | 179.22 (16) |
Symmetry codes: (i) x−1/2, y−1/2, z−1/2; (ii) −x+1, −y, −z+1; (iii) x+1/2, y+1/2, z+1/2. |
Funding information
Funding was provided by the National Science Foundation, Directorate for Mathematical and Physical Sciences (award No. DMR-2003932 awarded to JBB). NSF ChemMatCARS Sector 15 is supported by the Divisions of Chemistry (CHE) and Materials Research (DMR), National Science Foundation (grant No. NSF/CHE- 1834750). Use of the Advanced Photon Source, an Office of Science User Facility operated for the US Department of Energy (DOE), Office of Science, by Argonne National Laboratory was supported (contract No. DE-AC02-06CH11357).
References
Aakeröy, C. B., Wijethunga, T. K., Benton, J. & Desper, J. (2015a). Chem. Commun. 51, 2425–2428. Google Scholar
Aakeröy, C. B., Wijethunga, T. K. & Desper, J. (2015b). Chem. Eur. J. 21, 11029–11037. Web of Science PubMed Google Scholar
Angevine, D. J., Camacho, K. J., Rzayev, J. & Benedict, J. B. (2022a). Cryst. Growth Des. 22, 1594–1603. Web of Science CSD CrossRef CAS Google Scholar
Angevine, D. J., Camacho, K. J., Rzayev, J. & Benedict, J. B. (2022b). CrystEngComm, 24, 6155–6164. Web of Science CSD CrossRef CAS Google Scholar
Borchers, T. H., Topić, F., Christopherson, J. C., Bushuyev, O. S., Vainauskas, J., Titi, H. M., Friščić, T. & Barrett, C. J. (2022). Nat. Chem. 14, 574–581. Web of Science CSD CrossRef CAS PubMed Google Scholar
Bruker (2013). Apex3. Bruker AXS Inc., Madison, Wallingford, CT, USA. Google Scholar
Campillo-Alvarado, G., Li, C., Feng, Z., Hutchins, K. M., Swenson, D. C., Höpfl, H., Morales-Rojas, H. & MacGillivray, L. R. (2020). Organometallics, 39, 2197–2201. CAS Google Scholar
Chai, J.-D. & Head-Gordon, M. (2008). Phys. Chem. Chem. Phys. 10, 6615–6620. Web of Science CrossRef PubMed CAS Google Scholar
Cheng, Y., Datta, S. J., Zhou, S., Jia, J., Shekhah, O. & Eddaoudi, M. (2022). Chem. Soc. Rev. 51, 8300–8350. Web of Science CrossRef CAS PubMed Google Scholar
Cox, J. M., Walton, I. M. & Benedict, J. B. (2016). J. Mater. Chem. C. 4, 4028–4033. Web of Science CrossRef CAS Google Scholar
Dar, A. A. & Rashid, S. (2021). CrystEngComm, 23, 8007–8026. Web of Science CrossRef CAS Google Scholar
Desiraju, G. R. (2021). IUCrJ, 8, 148–149. Web of Science CrossRef CAS PubMed IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Duggirala, N. K., Perry, M. L., Almarsson, Ö. & Zaworotko, M. J. (2016). Chem. Commun. 52, 640–655. Web of Science CrossRef CAS Google Scholar
Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, K. N., Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, R. L., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, Ö., Foresman, J. B., Ortiz, J. V., Cioslowski, J. & Fox, D. J. (2013). Gaussian 09 Revision D.01. Gaussian Inc., Wallingford, CT, USA. Google Scholar
Fu, X., Ding, B. & D'Alessandro, D. (2023). Coord. Chem. Rev. 475, 214814. Web of Science CrossRef Google Scholar
Fukaminato, T., Kobatake, S., Kawai, T. & Irie, M. (2001). Proc. Jpn. Acad. Ser. B, 77, 30–35. Web of Science CrossRef Google Scholar
Gottlieb, H. E., Kotlyar, V. & Nudelman, A. (1997). J. Org. Chem. 62, 7512–7515. CrossRef PubMed CAS Web of Science Google Scholar
Guo, M., Sun, X., Chen, J. & Cai, T. (2021). Acta Pharm. Sin. B, 11, 2537–2564. Web of Science CrossRef CAS PubMed Google Scholar
Herder, M., Schmidt, B. M., Grubert, L., Pätzel, M., Schwarz, J. & Hecht, S. (2015). J. Am. Chem. Soc. 137, 2738–2747. Web of Science CSD CrossRef CAS PubMed Google Scholar
Jiang, M., Zhen, C., Li, S., Zhang, X. & Hu, W. (2021). Front. Chem. 9, 764628. Web of Science CrossRef PubMed Google Scholar
Kandambeth, S., Kale, V. S., Shekhah, O., Alshareef, H. N. & Eddaoudi, M. (2022). Adv. Energy Mater. 12, 2100177. Web of Science CrossRef Google Scholar
Karimi-Jafari, M., Padrela, L., Walker, G. M. & Croker, D. M. (2018). Cryst. Growth Des. 18, 6370–6387. CAS Google Scholar
Kent, R. V., Wiscons, R. A., Sharon, P., Grinstein, D., Frimer, A. A. & Matzger, A. J. (2018). Cryst. Growth Des. 18, 219–224. Web of Science CSD CrossRef CAS Google Scholar
Kitagawa, D., Nishi, H. & Kobatake, S. (2013). Angew. Chem. Int. Ed. 52, 9320–9322. Web of Science CSD CrossRef CAS Google Scholar
Kobatake, S., Shibata, K., Uchida, K. & Irie, M. (2000). J. Am. Chem. Soc. 122, 12135–12141. Web of Science CSD CrossRef CAS Google Scholar
Kobatake, S., Takami, S., Muto, H., Ishikawa, T. & Irie, M. (2007). Nature, 446, 778–781. Web of Science CSD CrossRef PubMed CAS Google Scholar
Kobatake, S., Uchida, K., Tsuchida, E. & Irie, M. (2002). Chem. Commun. pp. 2804–2805. Web of Science CSD CrossRef Google Scholar
Landenberger, K. B., Bolton, O. & Matzger, A. J. (2015). J. Am. Chem. Soc. 137, 5074–5079. Web of Science CSD CrossRef CAS PubMed Google Scholar
Müller, P., Muller, P., Herbst-Irmer, R., Crystallography, I. U., o , Press, O. U., Spek, A., Schneider, T. & Sawaya, M. (2006). Crystal Structure Refinement: a Crystallographer's Guide to SHELXL. Oxford University Press. Google Scholar
Nangia, A. K. & Desiraju, G. R. (2019). Angew. Chem. Int. Ed. 58, 4100–4107. Web of Science CrossRef CAS Google Scholar
Narayanan, A., Cao, D., Frazer, L., Tayi, A. S., Blackburn, A. K., Sue, A. C. H., Ketterson, J. B., Stoddart, J. F. & Stupp, S. I. (2017). J. Am. Chem. Soc. 139, 9186–9191. Web of Science CSD CrossRef CAS PubMed Google Scholar
Rajkumar, M. & Desiraju, G. R. (2021). IUCrJ, 8, 178–185. Web of Science CSD CrossRef CAS PubMed IUCr Journals Google Scholar
Ranjan, S., Devarapalli, R., Kundu, S., Saha, S., Deolka, S., Vangala, V. R. & Reddy, C. M. (2020). IUCrJ, 7, 173–183. Web of Science CSD CrossRef CAS PubMed IUCr Journals Google Scholar
Reutzel-Edens, S. M. & Bhardwaj, R. M. (2020). IUCrJ, 7, 955–964. Web of Science CrossRef CAS PubMed IUCr Journals Google Scholar
Rice, A. M., Martin, C. R., Galitskiy, V. A., Berseneva, A. A., Leith, G. A. & Shustova, N. B. (2020). Chem. Rev. 120, 8790–8813. Web of Science CrossRef CAS PubMed Google Scholar
Samanta, K., Samanta, J. & Natarajan, R. (2021). Cryst. Growth Des. 21, 166–190. Web of Science CSD CrossRef CAS Google Scholar
Shekhah, O., Chernikova, V., Belmabkhout, Y. & Eddaoudi, M. (2018). Crystals, 8, 412. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shibata, K., Muto, K., Kobatake, S. & Irie, M. (2002). J. Phys. Chem. A, 106, 209–214. Web of Science CrossRef CAS Google Scholar
Singh, S. S., Vasantha, K. Y., Sattur, A. P. & Thakur, T. S. (2016). CrystEngComm, 18, 1740–1751. Web of Science CSD CrossRef CAS Google Scholar
Sun, L., Wang, Y., Yang, F., Zhang, X. & Hu, W. (2019). Adv. Mater. 31, 1902328. Web of Science CrossRef Google Scholar
Tothadi, S. & Desiraju, G. R. (2012). Phil. Trans. R. Soc. A. 370, 2900–2915. Web of Science CSD CrossRef CAS PubMed Google Scholar
Yelgaonkar, S. P., Campillo-Alvarado, G. & MacGillivray, L. R. (2020). J. Am. Chem. Soc. 142, 20772–20777. Web of Science CSD CrossRef CAS PubMed Google Scholar
Zhang, J. & Tian, H. (2018). Adv. Opt. Mater. 6, 1701278. Web of Science CrossRef Google Scholar
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