research papers
Systematic synthesis of a 6-component organic-salt alloy of naftopidil, and pentanary, quaternary and ternary multicomponent crystals
aOrganic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, Maharashtra 411 008, India, bCentral NMR Facility, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, Maharashtra 411 008, India, and cSchool of Chemistry, University of Hyderabad, Prof. C. R. Rao Road, Gachibowli, Hyderabad, Telangana 500 046, India
*Correspondence e-mail: r.dandela@ncl.res.in, ak.nangia@ncl.res.in
The single-crystal X-ray structure of a 6-component organic-salt alloy (hexanary) of naftopidil (1) (an active pharmaceutical ingredient) with benzoic acid (2) and four different hydroxy-substituted benzoic acids, i.e. salicylic acid (3), 2,3-dihydroxybenzoic acid (4), 2,4-dihydroxybenzoic acid (5) and 2,6-dihydroxybenzoic acid (6), is reported. The hexanary assembly originates from the observation that the binary salts of naftopidil with the above acids are isostructural. In addition to the 6-component solid, we also describe five 5-component, ten 4-component, and ten 3-component organic-salt alloys of naftopidil (1) with (2)–(6). These alloys were obtained from different combinations of the acids with the drug. The synthetic design of the multicomponent organic alloys is based on the rationale of geometrical factors (shape and size) and chemical interactions (hydrogen bonds). The common supramolecular synthon in all these crystal structures was the cyclic N+—H⋯O− and O—H⋯O hydrogen-bonded motif of (9) graph set between the 2-hydroxyammonium group of naftopidil and the carboxylate anion. This ionic synthon is strong and robust, directing the isostructural assembly of naftopidil with up to five different in the together with the lower-level multicomponent adducts. Solution crystallization by slow evaporation provided the multicomponent organic salts and alloys which were characterized by a combination of single-crystal X-ray diffraction, powder X-ray diffraction, NMR and techniques.
Keywords: active pharmaceutical ingredients; crystal engineering; naftopidil; multicomponent solids; 6-component crystals; organic-salt alloys.
1. Introduction
Inorganic solid solutions are well known, widely prepared and extensively used in day-to-day life (Kumar, 2008). Fine tuning the ratio of components in inorganic alloys is relatively easy because of the spherical nature of atoms and ions involved in the multicomponent crystal structures. On the other hand, synthesis of organic alloys is challenging due to the different sizes, shapes and functional groups of the molecules. Hence, organic solid solutions are not so extensively studied in the literature. Organic alloys (Khoj et al., 2017; Lusi et al., 2015; Thomas et al., 2015) are different from organic salts and cocrystals; they are crystalline materials in which at least two different molecules are present, but not in a fixed stoichiometric ratio, whereas organic salts and cocrystals have a definite molecular stoichiometry. As a corollary, organic-salt alloys are characterized by the complete transfer of a proton from one molecule to another, with the components being present in variable stoichiometries in the ionic supramolecular structure (Mittapalli et al., 2015; Reddy et al., 2011; Suresh et al., 2017; Allu et al., 2017; Bond, 2007).
The rational design and synthesis of multicomponent pharmaceutical crystals is extremely challenging as the number of components increases, representing a significant advance for academia with immediate utility for the pharmaceutical industry (Almarsson et al., 2004; Duggirala et al., 2016; Bolla & Nangia, 2016; Thipparaboina et al., 2016). Crystallization is inherently a purification technique, and the outcome is mostly separation of the single-component crystals rather than a multicomponent assembly. Inclusion of more than three different molecules in the cocrystal becomes increasingly difficult (Tothadi & Desiraju, 2013). For instance, if one wishes to synthesize ternary cocrystals of A, B and C, then there is always a possibility to form ABC, but AB, AC, and solvates, hydrates and also polymorphs of the individual components are complicating side products. Hence, to reach the target multicomponent crystalline material is not always straightforward. The systematic design of multicomponent molecular crystals requires a proper understanding and optimization of the geometrical factors (molecular shape and size) and chemical interactions, such as hydrogen-bond donors and acceptors, i.e. supramolecular synthons (Desiraju, 1995; Tothadi et al., 2011). Multicomponent cocrystals have considerable importance in the pharmaceutical industry for the fine tuning of the physicochemical and pharmacokinetic properties of drugs such as solubility, dissolution, stability and bioavailability to name a few (Sanphui et al., 2012; Babu et al., 2012; Trask et al., 2005; Cherukuvada et al., 2011; Smith et al., 2011; Wouters & Quéré, 2012; Walsh et al., 2003). Crystal engineering (Desiraju, 1989) has reached the stage wherein from two component pharmaceutical cocrystals at the beginning of this millennium, (Almarsson et al., 2004), the recent record has become five components (Mir et al., 2016; Dubey et al., 2016) in 2016 and a 6-component organic adduct (Paul et al., 2018) has been reported recently while this manuscript was in the final stages. Furthermore, this is the first report of six different molecular components for an organic-salt alloy of an active pharmaceutical ingredient solved and refined by single-crystal X-ray diffraction. Binary, ternary and even quaternary cocrystals have been reported by several research groups during the past three decades (Reddy et al., 1994; Thakur et al., 2010; Sada et al., 2005; Hasell et al., 2012; Tothadi et al., 2017; Dabros et al., 2007; Allu et al., 2017). The bar was raised by Desiraju with the synthesis of 4- and 5-component molecular assemblies in 2016 (Mir et al., 2016; Dubey et al., 2016), and now a 6-component molecular solid (Paul et al., 2018) has been achieved by combining the design strategies of cocrystals and They upgraded the initial 4-component synthetic dead-end cocrystal to a 6-component by incorporating molecules of a similar shape/size. In addition to the challenge of synthetic design, geometric and chemical matching, and supramolecular assembly of multicomponent organic crystals with six components, there are difficulties caused by overlap of electron-density maps of molecules having similar size/placement of functional groups, and sometimes disorder in the cocrystal (Tothadi & Desiraju, 2013; Thakur et al., 2010; Hasell et al., 2012; Tothadi et al., 2017). Chemical factors start to taper off for 4-component crystals because weaker interactions provide only limited enthalpic advantage to molecular assembly in the cocrystal (Mir et al., 2016; Dubey et al., 2016). In this communication, we report the build-up of six different molecules/ions in an organic-salt alloy along with the lower 5-, 4- and 3-component structures based on a single robust supramolecular synthon. All in all, 25 multicomponent single-crystal structures, which include 20 salt alloys (one hexanary, three pentanary, eight quaternary and eight ternary) and five binary salts contain the same ionic (9) supramolecular synthon. An additional six alloys were characterized by powder X-ray diffraction (PXRD), NMR and (DSC) techniques in the absence of suitable single crystals (two each of ternary, quaternary and pentanary). Conceptually, our approach to a 6-component assembly based on a strong ionic synthon and isomeric carboxylic-acid replacement complements the Desiraju template (Paul et al., 2018) based on crystallographic inequivalences and halogen exchange.
2. Experimental
Naftopidil (in racemic form) was provided by Trimax Bio Sciences Ltd (India). The coformer and solvents (>99% purity) were purchased from TCI chemicals (Pune, India).
2.1. X-ray crystallography
A few single crystals obtained after crystallization were mounted on a Super Nova Dual Source X-ray Diffractometer system (Agilent Technologies) equipped with a CCD area detector. The X-ray generator was operated at 50 kV and 0.8 mA to generate Mo Kα radiation (λ = 0.71073 Å) and Cu Kα radiation (λ = 1.54178 Å) at 298 (2) K. Data reduction was performed using CrysAlisPro software (version 171.33.55, Agilent, 2010). The remaining crystals were mounted on a Bruker SMART APEX II single-crystal X-ray CCD diffractometer having graphite-monochromated Mo Kα radiation (λ = 0.71073 Å) at 100 and 293 K. The X-ray generator was operated at 50 kV and 30 mA. X-ray data acquisition was monitored by the APEX2 program suite. The data were corrected for Lorentz–polarization and absorption effects using SAINT and SADABS which are integral parts of the APEX2 package (Bruker, 2006). The structures were solved by and refined by full-matrix least squares based on F2 and using SHELXL (Sheldrick, 2017). Crystal structures were refined using OLEX software (version 2-1.0, Dolomanov et al., 2009) (Tables 1 and S2 of the supporting information). Anisotropic was performed for all non-hydrogen atoms. Most hydrogen atoms attached to heteroatoms were located using the difference Fourier map and some O—H hydrogen atoms were geometrically fixed using the HFIX command in SHELXL. All hydrogen atoms were refined isotropically. The structures were examined using the ADSYM subroutine of PLATON (Spek, 2005) to ensure that no additional symmetry could be applied to the models. Mercury software was used to prepare packing diagrams and molecular interactions. CIFs (CCDC references 1817125, 1817126, 1817127, 1817128, 1817129, 1817130, 1817146, 1817147, 1817148, 1817149, 1817150, 1817151, 1817158, 1817159, 1817160, 1817161, 1817162, 1817163, 1817164, 1817165, 1817166, 1817167, 1817168, 1817169, 1817170, 1840048) are available at https://www.ccdc.cam.ac.uk/data or as part of the supporting information.
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Refinement of organic-salt alloy crystal data: first, all non-hydrogen atoms were refined isotropically followed by anisotropic Substituted oxygen atoms of the acids (coformers) showed unusual ellipsoid electron density caused by multiple atoms in the envelope; free was performed on the atoms to find out the exact ratio of the corresponding acids. Then the organic-salt alloy composition of acid ratios was fixed by minimizing to an acceptable R factor. Finally, anisotropic was performed. To show the variable occupancy, PART, EADP and EXYZ commands were used in the .ins file. The acids of all salt alloys showed variable occupancy and disorder in the molecules which appeared as an unusual C—O—H geometry and short inter-distances: D—H⋯H—X. Reasonable chemical conclusions were derived from the crystallographic data.
2.2. Powder X-ray diffraction
All crystalline material PXRD data were recorded on a Rigaku, MicroMax-007HF using a high-intensity microfocus rotating-anode X-ray generator and a Cu Kα (λ = 1.54178 Å) radiation source with an Ni filter. Data collection was carried out using an aluminium holder at a scan speed of 1° min−1 and a step size of 0.02°. All crystalline samples were scanned over range of 2θ = 2–40° and the corresponding data were collected using Control Win software.
2.3. Thermal analysis
DSC was performed on a Mettler-Toledo DSC 822e module, (Mettler-Toledo, Columbus, OH). Samples were placed in crimped but vented aluminium pans for DSC experiments; the typical sample size was 3–5 mg. The temperature range for the heating curves was 30–300°C, and the sample was heated at a rate of 5°C min−1. Samples were purged in a stream of dry nitrogen flowing at 80 ml min−1.
2.4. NMR
All the one-dimensional 1H NMR experiments for the individual components, alloy crystals and physical mixtures were recorded in DMSO-d6 at 298 K on a Bruker Avance 500 MHz NMR spectrometer equipped with a BBO probe. Two-dimensional NMR (1H–1H DQF-COSY, TOCSY, ROESY, 13C–1H HSQC and HMBC) experiments for the 6-component alloy crystal were recorded in DMSO-d6 at 298 K on a Bruker Avance III HD 700 MHz NMR spectrometer equipped with a BBO probe. 2k complex points were acquired in direct dimension of all two-dimensional experiments except for HSQC, where 1k complex points were acquired. While 320 increments were recorded in the indirect dimension of COSY, TOCSY and HSQC, 512 and 576 increments were recorded for ROESY and HMBC, respectively.
Chemical-shift assignment and identification of all the components in the 6-component alloy crystal was achieved by detailed analysis of chemical shifts, resonance integral values, J-multiplicity and coupling constants in one-dimensional-1H experiments and further confirmed by correlations from two-dimensional experiments. The ratio of the individual components in the 6-component alloy crystal was determined from the ratio of the integrals of the resonances in its one-dimensional-1H experiment, which was acquired with a long d1 time of 10 s.
Identification of the rest of the alloy crystals (123, 1456, 12345, 12346, 12356, 12456 and 13456) was done by analysis of chemical shifts, resonance integral values, J-multiplicity and coupling constants in corresponding one-dimensional-1H experiments and further correlation to the chemical shifts in the 6-component alloy crystal.
3. Results and discussion
Naftopidil (Xu et al., 2017) is a selective α1-adrenergic receptor antagonist alpha-blocker antihypertensive drug. In the Biopharmaceutical Classification System (BCS) it is classified as a class IV drug of poor aqueous solubility and poor permeability (Xu et al., 2017; Blume & Schug, 1999; Chavda et al., 2010; Tsume et al., 2014). There are no reports in the literature on either salts or cocrystals of naftopidil; therefore, we aimed to prepare new solid forms of naftopidil as part of a cocrystal screen. Five 1:1 binary salts of naftopidil (1) with the hydroxy-substituted benzoic acid series were prepared, with benzoic acid (2), 2-hydroxybenzoic acid (3), 2,3-dihydroxybenzoic acid (4), 2,4-dihydroxybenzoic acid (5) and 2,6-dihydroxybenzoic acid (6) (Fig. 1). A 1:1 equimolar ratio of the drug and the coformer acid were taken in a mortar-pestle and ground for 15 min after the addition of 2–3 drops of solvent (MeOH). The ground product was added to MeOH (5 ml) and set aside for slow evaporation (a detailed experimental procedure is given in Table S1 of the supporting information). Good-quality single crystals (salts) were obtained from MeOH solution in a week, which were solved by single-crystal X-ray diffraction (Table 1). Interestingly, the five binary salts are isostructural (Table 1) and assemble via the (9) motif where proton transfer from the coformer acid to the drug (1) and an N+−H···O− plus O−H···O hydrogen bond is noted (Fig. 2). The novel salts of naftopidil were further characterized by PXRD (Fig. S6a) and DSC (Fig. S1). In the Cambridge Structural Database (CSD), there are 130 structures with the (9) motif [Fig. 1(b), Table S4]. The recurrence of the (9) synthon directs isostructurality, similar intermolecular interactions and crystal packing. The crystal structures of the individual benzoic acids are quite different from each other (analyzed from the CSD), highlighting the significance of the cyclic synthon (9) in directing the multi-component structures. This observation suggested the synthesis of higher order multicomponent (3-, 4-, 5-component) salts or organic alloys (Fig. 3). To test the robustness of the (9) synthon in this family, the salt of naftopidil (1) with 2,4,6-trihydroxybenzoic acid (as a surrogate of multiple hydroxybenzoic acids occupying the same site) was prepared, and interestingly it also shows a similar compared with the dihydroxybenzoic acid binary salts (Fig. S44). This observation added confidence to the next experiments on higher-component assemblies. By considering the same supramolecular synthon (hydrogen bonds) as well as similar molecular size of the acids, and isostructurality of the binary crystal structures [Table 1, all crystallized in the P21/c except (16) (P21)], a 6-component organic-salt alloy was synthesized. Naftopidil (1) 1 mmol, and 0.2 mmol of each of the five benzoic acids [(2), (3), (4), (5), (6); sum up to 1 mmol] were added to 5 ml MeOH and kept at ambient temperature. Good-quality single crystals suitable for X-ray diffraction were obtained in a week (Fig. 4a). In the alloy crystal which diffracted in P21/c there is one full molecule of naftopidil (1) and different ratios of acids (variable occupancy) depending on the size and hydrogen-bonding groups in the coformer. The site-occupancy factors (SOF) in the hexanary alloy are: naftopidil (1) 1.0, benzoic acid (2) 0.12, 2-hydroxybenzoic acid (3) 0.27, 2,3-dihydroxybenzoic acid (4) 0.14, 2,4-dihydroxybenzoic acid (5) 0.20 and 2,6-dihydroxybenzoic acid (6) 0.27 (Fig. 4b). The SOF values of the individual acids were derived from the free of respective carbon- or oxygen-atom electron-density maps to reach the lowest R factor (see Section 2 and Table S3). The correctness of the solution was confirmed by an overlay of the experimental PXRD of the 6-component alloy with the calculated powder X-ray line pattern from the (Fig. 4d). Similar to the binary salts, the carboxylic acid proton is completely transferred to the N atom of (1) together with the O—H⋯O hydrogen bond of (9) in the hexanary alloy (123456). By applying a similar procedure, 25 organic-salt alloys of pentanary, quaternary and ternary composition (solid solutions) were synthesized to confirm the robustness of the strategy for multicomponent organic-salt alloys anchored by the (9) synthon. The theoretical combinations will yield five pentanary, ten quaternary and ten ternary component crystals of naftopidil (1). For the synthesis of 5-component organic alloys, 1 mmol of (1) and 0.25 mmol of four different acids were used for cocrystallization (Table 2); 4-component organic alloys were synthesised using 1 mmol of (1) and 0.33 mmol each of the acids; and 3-component organic alloys were synthesised using 1 mmol of (1) and 0.5 mmol of the corresponding acids.
‡Hexacomponent (123456) alloy: 1 mmol of (1) and 0.2 mmol of each acid. §Pentanary alloy: 1 mmol of (1) and 0.25 mmol of each aromatic acid. ¶Quaternary alloy: 1 mmol of (1) and 0.33 mmol of each acid. ††Ternary alloy: 1 mmol of (1) and 0.50 mmol of each acid. ‡‡Stacked 1H NMR plots for these crystals along with their components are provided in the supporting information. §§Crystalline solids were obtained, but the single-crystal data quality was poor. |
The crystal packing diagrams of pentanary, quaternary and ternary alloys (Fig. 5) are similar except for the difference in the hydroxy-substituted benzoic acid portion of the structure. The similar packing of 2- to 6-component organic alloys is driven by the strong ionic (9) synthon geometry, which is a recurring motif in all of the crystal structures. The remaining alkyl and phenyl groups adjust with the close packing of molecules. DSC of the 6-component organic-salt alloy showed a single, sharp endotherm at 173°C which is neither the melting point of naftopidil, nor matches with any of the single-component acids, nor the binary salts of naftopidil with acids (Figs. 4c and S5a). Further characterization of the hexanary alloy (123456) was carried out using NMR spectroscopy, large single crystals of the alloy were dissolved in DMSO-d6 and 1H, 13C, COSY, TOCSY, HSQC and HMBC were acquired along with the individual 1H NMR of all six constituent components (Fig. 6). A correlative analysis of these spectra revealed the presence of all the six individual components in the salt-alloy crystal. The integral ratios of 1H NMR resonances of the crystal support the presence of (2) ∼8%, (3) ∼29%, (4) ∼24%, (5) ∼17% and (6) ∼22% and naftopidil (1) 100%. The occupancy values from the SOF of acids in the are (2) 0.12, (3) 0.27, (4) 0.14, (5) 0.20 and (6) 0.27. The maximum discrepancy between the NMR and single-crystal occupancy values (8–10%) could be the result of natural variation in the stoichiometry of the components in the hexanary alloy crystals and/or slight inhomogeneity of the NMR sample not being a single crystal. The bulk purity was established by PXRD (Fig. 4d). A series of 1H NMR experiments confirmed the ternary, quaternary and pentanary organic alloys (Figs. S11–S19). The single crystal X-ray structure (Figs. S20–S44), PXRD (Figs. S6a–S10), DSC (Figs. S1–S5b) and liquid chromatography–mass spectrometry (Figs. S45–S47) of naftopidil salt/alloys are given in the supporting information. In several cases, single-crystal structures were harvested and the structures were satisfactorily solved by X-ray diffraction. For others, crystals were obtained but the quality was not satisfactory for X-ray data collection on a laboratory diffractometer and so complementary NMR was used. The controlled synthesis of multicomponent crystals has applications in the pharmaceutical industry for the formulation of multicomponent drugs as cocrystals and solid solutions. In certain drugs the side effects can be minimized, while administration of two different drugs with synergistic action could mitigate side effects (Zhao et al., 2013; Prost et al., 2015). The efficacy of the 1:1 cocrystal-salt combination is enhanced in Valsartan (angiotensin receptor blocker) and Sacubitril (neprilsin inhibitor), Entresto (LCZ696 clinical candidate) (Jessup, 2014; McMurray et al., 2014), with a reduced risk of cardiovascular death during hospitalization of patients. Diverse applications of cocrystals and solid solutions and eutectics (multicomponent crystals) have been reported (Goldberg et al., 1966; Cherukuvada & Nangia, 2014; Braga et al., 2009; Romasanta et al., 2017; Mishra et al., 2015, Lusi, 2018).
4. Conclusions
We have successfully designed a hexacomponent organic-salt alloy of an active pharmaceutical ingredient by geometrical and chemical optimization based on a strong ionic (9) synthon. The generality of our method is demonstrated by the synthesis of over 26 organic-salt alloys by considering five isostructural binary salts which could lead to the manufacture of multicomponent pharmaceutical adducts as improved drugs.
Supporting information
https://doi.org/10.1107/S2052252518014057/ed5016sup1.cif
contains datablocks 12, 13, 14, 15, 16, 123, 124, 126, 134, 135, 136, 145, 146, 1234, 1235, 1236, 1245, 1246, 1346, 1356, 1456, 12345, 12346, 12356, 123456, platon_pl. DOI:Supporting tables, figures and schemes. DOI: https://doi.org/10.1107/S2052252518014057/ed5016sup2.pdf
Cell
SAINT v8.37A (Bruker, 2015) for platon_pl. Data reduction: SAINT v8.37A (Bruker, 2015) for platon_pl. Program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014) for (15), 123, 124, 126, 134, 135, 136, 145, 146, 1234, 1235, 1236, 1245, 1246, 1346, 1356, 1456, 12345, 12346, 12356, 123456, platon_pl. Program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016) for (12), (13), (14), (15), (16), 123, 124, 126, 134, 135, 136, 145, 146, 1234, 1235, 1236, 1245, 1246, 1346, 1356, 1456, 12345, 12346, 12356, 123456; SHELXL (Sheldrick, 2015) for platon_pl. Molecular graphics: Olex2 (Dolomanov et al., 2009) for platon_pl. Software used to prepare material for publication: Olex2 (Dolomanov et al., 2009) for platon_pl.C31H34N2O5 | F(000) = 1096 |
Mr = 514.60 | Dx = 1.299 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0695 (2) Å | Cell parameters from 8847 reflections |
b = 17.7360 (3) Å | θ = 3.5–27.3° |
c = 13.5179 (3) Å | µ = 0.09 mm−1 |
β = 97.3794 (19)° | T = 293 K |
V = 2632.00 (9) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.1 × 0.1 mm |
SuperNova, Dual, Cu at zero, Eos diffractometer | Rint = 0.042 |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 25.0°, θmin = 3.0° |
Tmin = 0.726, Tmax = 1.000 | h = −13→13 |
24778 measured reflections | k = −21→21 |
4626 independent reflections | l = −16→16 |
3831 reflections with I > 2σ(I) |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.153 | w = 1/[σ2(Fo2) + (0.0374P)2 + 2.5351P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
4626 reflections | Δρmax = 0.44 e Å−3 |
345 parameters | Δρmin = −0.29 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N19 | −0.00290 (18) | 0.15713 (11) | 0.05433 (15) | 0.0402 (5) | |
H19 | −0.033401 | 0.208165 | 0.038527 | 0.048* | |
O28 | −0.29866 (17) | −0.05518 (11) | 0.04788 (15) | 0.0558 (5) | |
O38 | −0.08800 (19) | 0.28812 (11) | −0.02422 (18) | 0.0660 (6) | |
C22 | −0.2959 (2) | 0.02359 (14) | −0.0914 (2) | 0.0429 (6) | |
N16 | −0.18971 (19) | 0.05793 (12) | −0.03937 (15) | 0.0430 (5) | |
O11 | 0.31024 (19) | 0.26428 (12) | 0.19564 (16) | 0.0668 (6) | |
C17 | −0.1158 (2) | 0.10229 (16) | −0.0994 (2) | 0.0487 (6) | |
H17A | −0.156072 | 0.149824 | −0.117458 | 0.058* | |
H17B | −0.106094 | 0.075297 | −0.160254 | 0.058* | |
C18 | 0.0069 (2) | 0.11681 (15) | −0.04107 (19) | 0.0463 (6) | |
H18A | 0.048368 | 0.069145 | −0.026624 | 0.056* | |
H18B | 0.055451 | 0.146740 | −0.081249 | 0.056* | |
O14 | 0.0612 (2) | 0.27108 (12) | 0.20302 (18) | 0.0731 (6) | |
H14 | 0.072723 | 0.292338 | 0.151192 | 0.110* | |
C23 | −0.3512 (2) | −0.03588 (14) | −0.0458 (2) | 0.0459 (6) | |
C21 | −0.2099 (2) | 0.10227 (15) | 0.0488 (2) | 0.0478 (6) | |
H21A | −0.262996 | 0.074695 | 0.087753 | 0.057* | |
H21B | −0.249368 | 0.149517 | 0.027967 | 0.057* | |
C30 | −0.0243 (2) | 0.40356 (14) | −0.08942 (19) | 0.0436 (6) | |
C20 | −0.0908 (2) | 0.11780 (15) | 0.11153 (19) | 0.0463 (6) | |
H20A | −0.105126 | 0.148687 | 0.168084 | 0.056* | |
H20B | −0.055381 | 0.070535 | 0.137076 | 0.056* | |
C2 | 0.4780 (3) | 0.31099 (15) | 0.1257 (2) | 0.0525 (7) | |
C27 | −0.3429 (3) | 0.04361 (16) | −0.1873 (2) | 0.0536 (7) | |
H27 | −0.307032 | 0.082861 | −0.218676 | 0.064* | |
C36 | −0.0009 (3) | 0.33091 (16) | −0.0325 (2) | 0.0529 (7) | |
C15 | 0.1205 (2) | 0.16314 (15) | 0.1121 (2) | 0.0495 (7) | |
H15A | 0.173213 | 0.189686 | 0.071800 | 0.059* | |
H15B | 0.153161 | 0.112718 | 0.123880 | 0.059* | |
C1 | 0.4341 (3) | 0.26841 (15) | 0.2029 (2) | 0.0564 (7) | |
C25 | −0.4961 (3) | −0.05092 (18) | −0.1926 (3) | 0.0637 (8) | |
H25 | −0.563208 | −0.075693 | −0.226219 | 0.076* | |
C3 | 0.3991 (3) | 0.35086 (17) | 0.0534 (2) | 0.0564 (7) | |
H3 | 0.315203 | 0.347252 | 0.053214 | 0.068* | |
C7 | 0.6055 (3) | 0.31505 (16) | 0.1226 (2) | 0.0576 (8) | |
C31 | −0.1400 (3) | 0.42284 (16) | −0.1314 (2) | 0.0529 (7) | |
H31 | −0.204454 | 0.390046 | −0.126242 | 0.063* | |
C26 | −0.4424 (3) | 0.00647 (18) | −0.2380 (2) | 0.0621 (8) | |
H26 | −0.472369 | 0.020646 | −0.302750 | 0.075* | |
C8 | 0.6851 (3) | 0.27791 (18) | 0.1972 (3) | 0.0691 (9) | |
H8 | 0.768532 | 0.278071 | 0.194302 | 0.083* | |
C13 | 0.1248 (3) | 0.20306 (16) | 0.2113 (2) | 0.0573 (7) | |
H13 | 0.084897 | 0.170293 | 0.255584 | 0.069* | |
C35 | 0.0704 (3) | 0.45260 (17) | −0.0989 (2) | 0.0580 (7) | |
H35 | 0.149157 | 0.440320 | −0.071064 | 0.070* | |
C4 | 0.4446 (3) | 0.3944 (2) | −0.0157 (2) | 0.0656 (8) | |
H4 | 0.391774 | 0.421552 | −0.061611 | 0.079* | |
C24 | −0.4507 (3) | −0.07224 (16) | −0.0967 (2) | 0.0562 (7) | |
H24 | −0.487532 | −0.111471 | −0.066079 | 0.067* | |
C12 | 0.2559 (3) | 0.21239 (18) | 0.2571 (2) | 0.0664 (9) | |
H12A | 0.259778 | 0.231753 | 0.324528 | 0.080* | |
H12B | 0.297983 | 0.164338 | 0.259281 | 0.080* | |
C10 | 0.5134 (3) | 0.23672 (17) | 0.2766 (3) | 0.0697 (9) | |
H10 | 0.484180 | 0.211628 | 0.329093 | 0.084* | |
O37 | 0.1033 (2) | 0.31872 (16) | 0.0077 (3) | 0.1091 (11) | |
C34 | 0.0484 (3) | 0.51985 (18) | −0.1495 (2) | 0.0681 (9) | |
H34 | 0.112582 | 0.552623 | −0.155788 | 0.082* | |
C6 | 0.6487 (3) | 0.3594 (2) | 0.0478 (3) | 0.0689 (9) | |
H6 | 0.731871 | 0.361659 | 0.043977 | 0.083* | |
C32 | −0.1613 (3) | 0.49061 (18) | −0.1813 (2) | 0.0639 (8) | |
H32 | −0.239969 | 0.503437 | −0.208732 | 0.077* | |
C5 | 0.5704 (3) | 0.3988 (2) | −0.0186 (3) | 0.0722 (9) | |
H5 | 0.600574 | 0.428877 | −0.066148 | 0.087* | |
C33 | −0.0674 (4) | 0.53855 (17) | −0.1905 (2) | 0.0671 (9) | |
H33 | −0.081726 | 0.583903 | −0.224489 | 0.080* | |
C9 | 0.6398 (3) | 0.24208 (18) | 0.2730 (3) | 0.0794 (11) | |
H9 | 0.693385 | 0.220541 | 0.323871 | 0.095* | |
C29 | −0.3511 (3) | −0.11615 (19) | 0.0960 (3) | 0.0731 (9) | |
H29A | −0.347591 | −0.161164 | 0.057021 | 0.110* | |
H29B | −0.434533 | −0.104658 | 0.102352 | 0.110* | |
H29C | −0.306681 | −0.123735 | 0.160991 | 0.110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N19 | 0.0431 (12) | 0.0306 (10) | 0.0474 (12) | −0.0010 (9) | 0.0074 (9) | 0.0015 (9) |
O28 | 0.0559 (12) | 0.0490 (11) | 0.0621 (12) | −0.0068 (9) | 0.0061 (9) | 0.0137 (9) |
O38 | 0.0568 (12) | 0.0443 (11) | 0.0979 (17) | −0.0010 (10) | 0.0132 (11) | 0.0186 (11) |
C22 | 0.0418 (13) | 0.0357 (13) | 0.0512 (15) | 0.0006 (11) | 0.0064 (11) | −0.0014 (11) |
N16 | 0.0450 (12) | 0.0392 (11) | 0.0456 (12) | −0.0051 (9) | 0.0082 (9) | −0.0004 (9) |
O11 | 0.0573 (13) | 0.0648 (13) | 0.0736 (14) | −0.0117 (10) | −0.0101 (10) | 0.0169 (11) |
C17 | 0.0540 (16) | 0.0480 (15) | 0.0450 (15) | −0.0053 (13) | 0.0101 (12) | 0.0009 (12) |
C18 | 0.0469 (15) | 0.0438 (14) | 0.0502 (15) | −0.0041 (12) | 0.0141 (12) | −0.0025 (12) |
O14 | 0.0904 (17) | 0.0547 (13) | 0.0737 (15) | 0.0027 (12) | 0.0082 (13) | −0.0074 (11) |
C23 | 0.0470 (15) | 0.0356 (13) | 0.0555 (16) | 0.0027 (11) | 0.0084 (12) | −0.0011 (12) |
C21 | 0.0503 (15) | 0.0421 (14) | 0.0532 (16) | −0.0038 (12) | 0.0147 (12) | −0.0043 (12) |
C30 | 0.0501 (15) | 0.0398 (14) | 0.0419 (14) | −0.0020 (12) | 0.0100 (11) | 0.0006 (11) |
C20 | 0.0542 (16) | 0.0422 (14) | 0.0444 (14) | −0.0066 (12) | 0.0134 (12) | −0.0011 (11) |
C2 | 0.0512 (16) | 0.0423 (15) | 0.0607 (17) | −0.0015 (12) | −0.0046 (13) | −0.0138 (13) |
C27 | 0.0607 (18) | 0.0430 (15) | 0.0560 (17) | −0.0025 (13) | 0.0035 (14) | 0.0026 (13) |
C36 | 0.0484 (16) | 0.0497 (16) | 0.0605 (18) | 0.0015 (13) | 0.0065 (13) | 0.0077 (13) |
C15 | 0.0475 (15) | 0.0395 (14) | 0.0605 (17) | −0.0014 (12) | 0.0025 (13) | 0.0011 (12) |
C1 | 0.0578 (18) | 0.0385 (15) | 0.0683 (19) | −0.0046 (13) | −0.0102 (14) | −0.0040 (13) |
C25 | 0.0572 (18) | 0.0538 (18) | 0.076 (2) | −0.0077 (15) | −0.0063 (16) | −0.0126 (16) |
C3 | 0.0503 (16) | 0.0605 (18) | 0.0561 (17) | −0.0022 (14) | −0.0017 (13) | −0.0038 (14) |
C7 | 0.0537 (17) | 0.0491 (16) | 0.0669 (19) | 0.0036 (14) | −0.0043 (14) | −0.0226 (15) |
C31 | 0.0533 (17) | 0.0471 (16) | 0.0584 (17) | −0.0014 (13) | 0.0082 (13) | 0.0037 (13) |
C26 | 0.0666 (19) | 0.0592 (18) | 0.0565 (18) | −0.0016 (15) | −0.0077 (15) | −0.0056 (15) |
C8 | 0.0527 (18) | 0.0514 (18) | 0.098 (3) | 0.0074 (15) | −0.0103 (18) | −0.0190 (18) |
C13 | 0.0671 (19) | 0.0458 (16) | 0.0580 (18) | −0.0075 (14) | 0.0039 (14) | 0.0017 (13) |
C35 | 0.0606 (18) | 0.0597 (18) | 0.0528 (17) | −0.0129 (15) | 0.0035 (14) | 0.0057 (14) |
C4 | 0.0575 (18) | 0.080 (2) | 0.0571 (18) | −0.0010 (16) | 0.0005 (15) | −0.0009 (16) |
C24 | 0.0506 (16) | 0.0433 (15) | 0.075 (2) | −0.0057 (13) | 0.0083 (15) | −0.0028 (14) |
C12 | 0.079 (2) | 0.0564 (18) | 0.0596 (19) | −0.0169 (16) | −0.0070 (16) | 0.0090 (15) |
C10 | 0.075 (2) | 0.0442 (17) | 0.082 (2) | −0.0061 (15) | −0.0214 (18) | 0.0066 (16) |
O37 | 0.0593 (15) | 0.098 (2) | 0.163 (3) | −0.0055 (14) | −0.0130 (16) | 0.072 (2) |
C34 | 0.093 (3) | 0.0565 (19) | 0.0536 (18) | −0.0301 (18) | 0.0056 (17) | 0.0063 (15) |
C6 | 0.0521 (18) | 0.082 (2) | 0.073 (2) | −0.0026 (17) | 0.0120 (16) | −0.0241 (19) |
C32 | 0.070 (2) | 0.0567 (19) | 0.063 (2) | 0.0093 (16) | 0.0031 (16) | 0.0111 (15) |
C5 | 0.060 (2) | 0.098 (3) | 0.0589 (19) | −0.0041 (19) | 0.0091 (16) | −0.0056 (18) |
C33 | 0.110 (3) | 0.0388 (16) | 0.0510 (17) | −0.0017 (17) | 0.0062 (18) | 0.0054 (13) |
C9 | 0.077 (2) | 0.0449 (18) | 0.104 (3) | 0.0071 (17) | −0.033 (2) | −0.0027 (19) |
C29 | 0.088 (2) | 0.0580 (19) | 0.076 (2) | −0.0123 (17) | 0.0202 (19) | 0.0163 (17) |
N19—C15 | 1.488 (3) | C2—C7 | 1.420 (4) |
N19—C18 | 1.491 (3) | C2—C1 | 1.423 (4) |
N19—C20 | 1.491 (3) | C27—C26 | 1.386 (4) |
O28—C23 | 1.367 (3) | C36—O37 | 1.229 (3) |
O28—C29 | 1.423 (3) | C15—C13 | 1.511 (4) |
O38—C36 | 1.243 (3) | C1—C10 | 1.361 (4) |
C22—C27 | 1.381 (4) | C25—C26 | 1.364 (4) |
C22—C23 | 1.402 (4) | C25—C24 | 1.382 (4) |
C22—N16 | 1.426 (3) | C3—C4 | 1.359 (4) |
N16—C17 | 1.455 (3) | C7—C6 | 1.411 (5) |
N16—C21 | 1.469 (3) | C7—C8 | 1.414 (4) |
O11—C1 | 1.364 (4) | C31—C32 | 1.384 (4) |
O11—C12 | 1.424 (4) | C8—C9 | 1.355 (5) |
C17—C18 | 1.503 (4) | C13—C12 | 1.512 (4) |
O14—C13 | 1.394 (4) | C35—C34 | 1.381 (4) |
C23—C24 | 1.381 (4) | C4—C5 | 1.400 (4) |
C21—C20 | 1.499 (4) | C10—C9 | 1.410 (5) |
C30—C31 | 1.376 (4) | C34—C33 | 1.370 (5) |
C30—C35 | 1.380 (4) | C6—C5 | 1.358 (5) |
C30—C36 | 1.506 (4) | C32—C33 | 1.361 (5) |
C2—C3 | 1.414 (4) | ||
C15—N19—C18 | 108.95 (19) | O38—C36—C30 | 118.9 (3) |
C15—N19—C20 | 112.2 (2) | N19—C15—C13 | 114.9 (2) |
C18—N19—C20 | 110.42 (19) | C10—C1—O11 | 125.3 (3) |
C23—O28—C29 | 117.6 (2) | C10—C1—C2 | 120.5 (3) |
C27—C22—C23 | 118.2 (2) | O11—C1—C2 | 114.2 (2) |
C27—C22—N16 | 122.7 (2) | C26—C25—C24 | 120.0 (3) |
C23—C22—N16 | 118.9 (2) | C4—C3—C2 | 120.6 (3) |
C22—N16—C17 | 116.3 (2) | C6—C7—C8 | 122.2 (3) |
C22—N16—C21 | 115.3 (2) | C6—C7—C2 | 118.6 (3) |
C17—N16—C21 | 108.5 (2) | C8—C7—C2 | 119.0 (3) |
C1—O11—C12 | 119.3 (2) | C30—C31—C32 | 120.5 (3) |
N16—C17—C18 | 109.6 (2) | C25—C26—C27 | 119.8 (3) |
N19—C18—C17 | 112.0 (2) | C9—C8—C7 | 120.1 (3) |
O28—C23—C24 | 124.2 (2) | O14—C13—C15 | 112.1 (2) |
O28—C23—C22 | 115.9 (2) | O14—C13—C12 | 112.7 (3) |
C24—C23—C22 | 119.9 (3) | C15—C13—C12 | 109.5 (3) |
N16—C21—C20 | 110.0 (2) | C30—C35—C34 | 120.2 (3) |
C31—C30—C35 | 118.9 (3) | C3—C4—C5 | 120.6 (3) |
C31—C30—C36 | 120.9 (2) | C23—C24—C25 | 120.7 (3) |
C35—C30—C36 | 120.2 (3) | O11—C12—C13 | 106.7 (2) |
N19—C20—C21 | 112.2 (2) | C1—C10—C9 | 119.8 (3) |
C3—C2—C7 | 118.8 (3) | C33—C34—C35 | 120.4 (3) |
C3—C2—C1 | 122.3 (3) | C5—C6—C7 | 120.9 (3) |
C7—C2—C1 | 118.9 (3) | C33—C32—C31 | 120.2 (3) |
C22—C27—C26 | 121.4 (3) | C6—C5—C4 | 120.4 (3) |
O37—C36—O38 | 123.2 (3) | C32—C33—C34 | 119.9 (3) |
O37—C36—C30 | 117.8 (3) | C8—C9—C10 | 121.5 (3) |
C31H34N2O6 | F(000) = 1128 |
Mr = 530.60 | Dx = 1.326 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.2350 (5) Å | Cell parameters from 3874 reflections |
b = 17.6516 (6) Å | θ = 3.7–25.6° |
c = 13.4798 (6) Å | µ = 0.09 mm−1 |
β = 96.269 (4)° | T = 293 K |
V = 2657.27 (18) Å3 | Block, colourless |
Z = 4 | 0.2 × 0.2 × 0.1 mm |
SuperNova, Dual, Cu at zero, Eos diffractometer | 3368 reflections with I > 2σ(I) |
ω scans | Rint = 0.040 |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 25.0°, θmin = 2.9° |
Tmin = 0.775, Tmax = 1.000 | h = −13→13 |
11084 measured reflections | k = −20→13 |
4667 independent reflections | l = −14→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.0452P)2 + 2.2386P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
4667 reflections | Δρmax = 0.32 e Å−3 |
355 parameters | Δρmin = −0.17 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N19 | −0.0030 (2) | 0.15600 (13) | 0.55678 (18) | 0.0432 (6) | |
H19 | −0.032700 | 0.207436 | 0.542054 | 0.052* | |
N16 | −0.1869 (2) | 0.05713 (13) | 0.46401 (18) | 0.0450 (6) | |
O11 | 0.3073 (2) | 0.25938 (14) | 0.69631 (18) | 0.0678 (7) | |
O38 | −0.0910 (2) | 0.28816 (12) | 0.4783 (2) | 0.0683 (7) | |
O28 | −0.2972 (2) | −0.05571 (12) | 0.55185 (17) | 0.0589 (6) | |
C30 | −0.0335 (3) | 0.40427 (16) | 0.4086 (2) | 0.0437 (7) | |
C20 | 0.0069 (3) | 0.11664 (18) | 0.4599 (2) | 0.0489 (7) | |
H20A | 0.048363 | 0.068861 | 0.472686 | 0.059* | |
H20B | 0.054024 | 0.147531 | 0.419299 | 0.059* | |
O14 | 0.0615 (3) | 0.27156 (13) | 0.70335 (19) | 0.0713 (7) | |
H14 | 0.074836 | 0.292141 | 0.651157 | 0.107* | |
C17 | −0.2070 (3) | 0.10096 (18) | 0.5525 (2) | 0.0500 (8) | |
H17A | −0.259625 | 0.073038 | 0.591812 | 0.060* | |
H17B | −0.245714 | 0.148503 | 0.532440 | 0.060* | |
C21 | −0.1139 (3) | 0.10187 (18) | 0.4032 (2) | 0.0515 (8) | |
H21A | −0.153559 | 0.149620 | 0.385784 | 0.062* | |
H21B | −0.104124 | 0.074895 | 0.341959 | 0.062* | |
O37 | 0.0991 (2) | 0.32145 (14) | 0.5036 (2) | 0.0768 (8) | |
C18 | −0.0905 (3) | 0.11650 (17) | 0.6146 (2) | 0.0496 (8) | |
H18A | −0.105424 | 0.147531 | 0.671371 | 0.059* | |
H18B | −0.056143 | 0.068976 | 0.639982 | 0.059* | |
O39 | 0.1715 (2) | 0.44077 (17) | 0.4258 (2) | 0.0843 (9) | |
H39 | 0.175843 | 0.400301 | 0.455835 | 0.126* | |
C22 | −0.2909 (3) | 0.02277 (16) | 0.4123 (2) | 0.0457 (7) | |
C23 | −0.3470 (3) | −0.03653 (17) | 0.4588 (2) | 0.0488 (7) | |
C1 | 0.4293 (3) | 0.26424 (18) | 0.7072 (3) | 0.0593 (9) | |
C36 | −0.0077 (3) | 0.33278 (18) | 0.4666 (2) | 0.0527 (8) | |
C27 | −0.3349 (3) | 0.04253 (19) | 0.3164 (3) | 0.0591 (9) | |
H27 | −0.297993 | 0.081379 | 0.284611 | 0.071* | |
C15 | 0.1180 (3) | 0.16194 (17) | 0.6129 (2) | 0.0522 (8) | |
H15A | 0.170024 | 0.188774 | 0.572006 | 0.063* | |
H15B | 0.150171 | 0.111287 | 0.624206 | 0.063* | |
C2 | 0.4776 (3) | 0.30820 (18) | 0.6329 (3) | 0.0550 (8) | |
C31 | 0.0572 (3) | 0.45506 (19) | 0.3927 (2) | 0.0538 (8) | |
C13 | 0.1212 (3) | 0.20191 (18) | 0.7124 (3) | 0.0578 (9) | |
H13 | 0.079052 | 0.169815 | 0.756517 | 0.069* | |
C25 | −0.4877 (3) | −0.0506 (2) | 0.3124 (3) | 0.0708 (11) | |
H25 | −0.553916 | −0.075000 | 0.279224 | 0.085* | |
C33 | −0.0860 (4) | 0.53801 (19) | 0.3055 (3) | 0.0683 (10) | |
H33 | −0.103683 | 0.583064 | 0.271253 | 0.082* | |
C32 | 0.0301 (4) | 0.52225 (19) | 0.3414 (2) | 0.0636 (10) | |
H32 | 0.090652 | 0.556436 | 0.331455 | 0.076* | |
C3 | 0.4040 (3) | 0.3492 (2) | 0.5606 (3) | 0.0598 (9) | |
H3 | 0.321192 | 0.345247 | 0.558409 | 0.072* | |
C7 | 0.6039 (3) | 0.3132 (2) | 0.6328 (3) | 0.0637 (10) | |
C34 | −0.1762 (3) | 0.4886 (2) | 0.3192 (3) | 0.0645 (9) | |
H34 | −0.254656 | 0.499570 | 0.293849 | 0.077* | |
C26 | −0.4326 (3) | 0.0060 (2) | 0.2663 (3) | 0.0686 (10) | |
H26 | −0.460480 | 0.020038 | 0.201379 | 0.082* | |
C24 | −0.4454 (3) | −0.07191 (19) | 0.4083 (3) | 0.0611 (9) | |
H24 | −0.483612 | −0.110570 | 0.439411 | 0.073* | |
C35 | −0.1498 (3) | 0.42220 (19) | 0.3710 (3) | 0.0572 (8) | |
H35 | −0.211399 | 0.388776 | 0.380955 | 0.069* | |
C4 | 0.4519 (3) | 0.3944 (2) | 0.4943 (3) | 0.0703 (10) | |
H4 | 0.401738 | 0.422230 | 0.448489 | 0.084* | |
C6 | 0.6502 (3) | 0.3595 (2) | 0.5608 (3) | 0.0735 (11) | |
H6 | 0.732603 | 0.362460 | 0.559105 | 0.088* | |
C10 | 0.5030 (4) | 0.2318 (2) | 0.7827 (3) | 0.0777 (12) | |
H10 | 0.471179 | 0.205877 | 0.833706 | 0.093* | |
C8 | 0.6772 (4) | 0.2752 (2) | 0.7089 (4) | 0.0795 (13) | |
H8 | 0.759910 | 0.275662 | 0.708406 | 0.095* | |
C5 | 0.5762 (3) | 0.3998 (3) | 0.4938 (3) | 0.0774 (11) | |
H5 | 0.608064 | 0.430886 | 0.447697 | 0.093* | |
C9 | 0.6285 (4) | 0.2382 (2) | 0.7823 (4) | 0.0898 (15) | |
H9 | 0.678702 | 0.216366 | 0.833847 | 0.108* | |
C12 | 0.2504 (3) | 0.2092 (2) | 0.7587 (3) | 0.0689 (10) | |
H12A | 0.253544 | 0.229398 | 0.825815 | 0.083* | |
H12B | 0.289537 | 0.160124 | 0.761633 | 0.083* | |
C29 | −0.3513 (4) | −0.1164 (2) | 0.6005 (3) | 0.0770 (11) | |
H29A | −0.346259 | −0.162112 | 0.562553 | 0.116* | |
H29B | −0.433807 | −0.104662 | 0.605621 | 0.116* | |
H29C | −0.310128 | −0.123379 | 0.666124 | 0.116* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N19 | 0.0465 (14) | 0.0325 (12) | 0.0512 (15) | −0.0030 (11) | 0.0081 (11) | 0.0021 (11) |
N16 | 0.0466 (14) | 0.0421 (13) | 0.0465 (14) | −0.0051 (11) | 0.0068 (11) | −0.0017 (11) |
O11 | 0.0583 (15) | 0.0680 (15) | 0.0734 (16) | −0.0150 (12) | −0.0097 (12) | 0.0192 (13) |
O38 | 0.0611 (15) | 0.0421 (12) | 0.103 (2) | −0.0029 (11) | 0.0145 (13) | 0.0187 (13) |
O28 | 0.0594 (14) | 0.0510 (13) | 0.0660 (15) | −0.0111 (11) | 0.0051 (11) | 0.0134 (11) |
C30 | 0.0531 (18) | 0.0368 (15) | 0.0426 (16) | 0.0008 (13) | 0.0123 (13) | 0.0005 (13) |
C20 | 0.0499 (18) | 0.0450 (17) | 0.0537 (19) | −0.0040 (14) | 0.0148 (14) | −0.0010 (14) |
O14 | 0.093 (2) | 0.0524 (14) | 0.0694 (17) | −0.0033 (13) | 0.0147 (14) | −0.0036 (12) |
C17 | 0.0504 (18) | 0.0466 (17) | 0.0548 (19) | −0.0067 (14) | 0.0133 (14) | −0.0028 (14) |
C21 | 0.0568 (19) | 0.0530 (18) | 0.0457 (18) | −0.0076 (15) | 0.0095 (14) | 0.0038 (15) |
O37 | 0.0581 (16) | 0.0701 (17) | 0.100 (2) | 0.0031 (13) | −0.0009 (14) | 0.0335 (15) |
C18 | 0.059 (2) | 0.0442 (17) | 0.0479 (18) | −0.0068 (15) | 0.0148 (14) | −0.0001 (14) |
O39 | 0.0577 (16) | 0.099 (2) | 0.093 (2) | −0.0208 (15) | −0.0053 (14) | 0.0319 (17) |
C22 | 0.0433 (17) | 0.0387 (16) | 0.0548 (19) | 0.0005 (13) | 0.0049 (14) | −0.0022 (14) |
C23 | 0.0472 (17) | 0.0398 (16) | 0.060 (2) | 0.0019 (14) | 0.0073 (15) | 0.0011 (14) |
C1 | 0.062 (2) | 0.0399 (17) | 0.071 (2) | −0.0045 (16) | −0.0136 (17) | −0.0032 (16) |
C36 | 0.057 (2) | 0.0436 (18) | 0.059 (2) | 0.0023 (16) | 0.0142 (16) | 0.0030 (15) |
C27 | 0.067 (2) | 0.0500 (19) | 0.058 (2) | −0.0034 (17) | −0.0024 (17) | 0.0018 (16) |
C15 | 0.0508 (18) | 0.0397 (16) | 0.065 (2) | −0.0037 (14) | 0.0023 (15) | 0.0021 (15) |
C2 | 0.0507 (19) | 0.0459 (18) | 0.066 (2) | −0.0038 (15) | −0.0046 (16) | −0.0125 (16) |
C31 | 0.059 (2) | 0.0553 (19) | 0.0459 (18) | −0.0104 (16) | 0.0019 (15) | 0.0021 (15) |
C13 | 0.071 (2) | 0.0429 (18) | 0.059 (2) | −0.0119 (16) | 0.0037 (17) | 0.0052 (15) |
C25 | 0.059 (2) | 0.062 (2) | 0.087 (3) | −0.0064 (19) | −0.009 (2) | −0.016 (2) |
C33 | 0.105 (3) | 0.0421 (19) | 0.055 (2) | 0.003 (2) | −0.002 (2) | 0.0037 (16) |
C32 | 0.087 (3) | 0.053 (2) | 0.050 (2) | −0.0231 (19) | 0.0035 (18) | 0.0072 (16) |
C3 | 0.0485 (19) | 0.070 (2) | 0.061 (2) | −0.0065 (17) | 0.0022 (16) | −0.0001 (18) |
C7 | 0.054 (2) | 0.053 (2) | 0.081 (3) | 0.0034 (17) | −0.0070 (18) | −0.0264 (19) |
C34 | 0.067 (2) | 0.058 (2) | 0.068 (2) | 0.0101 (19) | 0.0049 (18) | 0.0088 (18) |
C26 | 0.069 (2) | 0.066 (2) | 0.067 (2) | −0.004 (2) | −0.0111 (19) | −0.0061 (19) |
C24 | 0.054 (2) | 0.0478 (19) | 0.081 (3) | −0.0089 (16) | 0.0060 (18) | −0.0044 (18) |
C35 | 0.055 (2) | 0.0511 (19) | 0.067 (2) | 0.0022 (16) | 0.0115 (16) | 0.0025 (16) |
C4 | 0.059 (2) | 0.089 (3) | 0.063 (2) | −0.004 (2) | 0.0071 (18) | 0.003 (2) |
C6 | 0.050 (2) | 0.089 (3) | 0.083 (3) | −0.005 (2) | 0.015 (2) | −0.028 (2) |
C10 | 0.089 (3) | 0.045 (2) | 0.091 (3) | −0.0039 (19) | −0.024 (2) | 0.0077 (19) |
C8 | 0.059 (2) | 0.057 (2) | 0.117 (4) | 0.0083 (19) | −0.016 (2) | −0.024 (2) |
C5 | 0.061 (2) | 0.102 (3) | 0.071 (3) | −0.007 (2) | 0.015 (2) | −0.004 (2) |
C9 | 0.082 (3) | 0.052 (2) | 0.125 (4) | 0.007 (2) | −0.038 (3) | −0.002 (2) |
C12 | 0.081 (3) | 0.059 (2) | 0.064 (2) | −0.0222 (19) | −0.0064 (19) | 0.0118 (18) |
C29 | 0.087 (3) | 0.063 (2) | 0.083 (3) | −0.017 (2) | 0.018 (2) | 0.017 (2) |
N19—C15 | 1.486 (4) | C23—C24 | 1.382 (4) |
N19—C18 | 1.493 (4) | C1—C10 | 1.365 (5) |
N19—C20 | 1.494 (4) | C1—C2 | 1.421 (5) |
N16—C22 | 1.429 (4) | C27—C26 | 1.385 (5) |
N16—C21 | 1.453 (4) | C15—C13 | 1.512 (5) |
N16—C17 | 1.460 (4) | C2—C3 | 1.408 (5) |
O11—C1 | 1.364 (4) | C2—C7 | 1.423 (5) |
O11—C12 | 1.421 (4) | C31—C32 | 1.390 (5) |
O38—C36 | 1.246 (4) | C13—C12 | 1.522 (5) |
O28—C23 | 1.360 (4) | C25—C26 | 1.361 (5) |
O28—C29 | 1.426 (4) | C25—C24 | 1.380 (5) |
C30—C35 | 1.386 (4) | C33—C34 | 1.365 (5) |
C30—C31 | 1.391 (4) | C33—C32 | 1.370 (5) |
C30—C36 | 1.496 (4) | C3—C4 | 1.353 (5) |
C20—C21 | 1.506 (4) | C7—C6 | 1.410 (6) |
O14—C13 | 1.399 (4) | C7—C8 | 1.413 (5) |
C17—C18 | 1.500 (4) | C34—C35 | 1.380 (5) |
O37—C36 | 1.263 (4) | C4—C5 | 1.400 (5) |
O39—C31 | 1.336 (4) | C6—C5 | 1.360 (6) |
C22—C27 | 1.377 (4) | C10—C9 | 1.415 (6) |
C22—C23 | 1.404 (4) | C8—C9 | 1.350 (6) |
C15—N19—C18 | 112.6 (2) | N19—C15—C13 | 114.6 (3) |
C15—N19—C20 | 109.1 (2) | C3—C2—C1 | 121.9 (3) |
C18—N19—C20 | 110.8 (2) | C3—C2—C7 | 118.5 (3) |
C22—N16—C21 | 115.9 (2) | C1—C2—C7 | 119.5 (3) |
C22—N16—C17 | 115.6 (2) | O39—C31—C32 | 118.6 (3) |
C21—N16—C17 | 108.7 (2) | O39—C31—C30 | 121.3 (3) |
C1—O11—C12 | 119.2 (3) | C32—C31—C30 | 120.1 (3) |
C23—O28—C29 | 117.3 (3) | O14—C13—C15 | 111.6 (3) |
C35—C30—C31 | 118.3 (3) | O14—C13—C12 | 112.8 (3) |
C35—C30—C36 | 120.3 (3) | C15—C13—C12 | 109.4 (3) |
C31—C30—C36 | 121.4 (3) | C26—C25—C24 | 120.0 (3) |
N19—C20—C21 | 112.0 (2) | C34—C33—C32 | 121.0 (3) |
N16—C17—C18 | 110.4 (3) | C33—C32—C31 | 119.9 (3) |
N16—C21—C20 | 109.9 (2) | C4—C3—C2 | 121.0 (3) |
N19—C18—C17 | 112.2 (2) | C6—C7—C8 | 123.0 (4) |
C27—C22—C23 | 118.4 (3) | C6—C7—C2 | 118.7 (3) |
C27—C22—N16 | 122.7 (3) | C8—C7—C2 | 118.2 (4) |
C23—C22—N16 | 118.8 (3) | C33—C34—C35 | 119.3 (3) |
O28—C23—C24 | 124.6 (3) | C25—C26—C27 | 119.7 (4) |
O28—C23—C22 | 116.0 (3) | C25—C24—C23 | 120.9 (3) |
C24—C23—C22 | 119.4 (3) | C34—C35—C30 | 121.4 (3) |
O11—C1—C10 | 125.1 (4) | C3—C4—C5 | 120.8 (4) |
O11—C1—C2 | 114.5 (3) | C5—C6—C7 | 121.0 (4) |
C10—C1—C2 | 120.4 (4) | C1—C10—C9 | 119.2 (4) |
O38—C36—O37 | 122.9 (3) | C9—C8—C7 | 120.7 (4) |
O38—C36—C30 | 119.6 (3) | C6—C5—C4 | 119.9 (4) |
O37—C36—C30 | 117.5 (3) | C8—C9—C10 | 121.7 (4) |
C22—C27—C26 | 121.6 (3) | O11—C12—C13 | 106.3 (3) |
C31H34N2O7 | F(000) = 1160 |
Mr = 546.60 | Dx = 1.347 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.3258 (4) Å | Cell parameters from 4413 reflections |
b = 17.8349 (7) Å | θ = 3.6–27.3° |
c = 13.4077 (7) Å | µ = 0.10 mm−1 |
β = 95.800 (4)° | T = 293 K |
V = 2694.4 (2) Å3 | Plate, colourless |
Z = 4 | 0.2 × 0.1 × 0.1 mm |
SuperNova, Dual, Cu at zero, Eos diffractometer | 3717 reflections with I > 2σ(I) |
ω scans | Rint = 0.041 |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 25.0°, θmin = 3.1° |
Tmin = 0.801, Tmax = 1.000 | h = −13→13 |
11635 measured reflections | k = −15→21 |
4734 independent reflections | l = −14→15 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.088 | H-atom parameters constrained |
wR(F2) = 0.256 | w = 1/[σ2(Fo2) + (0.0639P)2 + 8.6056P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max < 0.001 |
4734 reflections | Δρmax = 0.41 e Å−3 |
365 parameters | Δρmin = −0.29 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N19 | 0.9890 (3) | 0.1546 (2) | 0.0550 (3) | 0.0387 (9) | |
H19 | 0.956940 | 0.205109 | 0.041952 | 0.046* | |
O11 | 1.2935 (3) | 0.2612 (2) | 0.1969 (3) | 0.0553 (10) | |
N16 | 0.8098 (3) | 0.0556 (2) | −0.0386 (3) | 0.0392 (9) | |
O38 | 0.8899 (3) | 0.2848 (2) | −0.0247 (3) | 0.0604 (10) | |
O14 | 1.0478 (4) | 0.2665 (2) | 0.2074 (3) | 0.0610 (10) | |
H14 | 1.062560 | 0.290125 | 0.157652 | 0.092* | |
O28 | 0.7049 (3) | −0.0596 (2) | 0.0473 (3) | 0.0539 (9) | |
O40 | 1.1503 (3) | 0.4376 (2) | −0.0680 (3) | 0.0653 (11) | |
H40 | 1.154383 | 0.399166 | −0.034298 | 0.098* | |
C31 | 1.0377 (4) | 0.4505 (3) | −0.1023 (3) | 0.0431 (11) | |
O39 | 1.1066 (4) | 0.5679 (2) | −0.1577 (3) | 0.0720 (13) | |
H39 | 1.166833 | 0.550397 | −0.127270 | 0.108* | |
C17 | 0.8799 (5) | 0.1026 (3) | −0.0996 (4) | 0.0484 (12) | |
H17A | 0.839254 | 0.149775 | −0.114418 | 0.058* | |
H17B | 0.889380 | 0.077609 | −0.162587 | 0.058* | |
C18 | 1.0001 (4) | 0.1172 (3) | −0.0439 (4) | 0.0447 (12) | |
H18A | 1.042110 | 0.070103 | −0.032644 | 0.054* | |
H18B | 1.045983 | 0.148917 | −0.084277 | 0.054* | |
C27 | 0.6533 (4) | −0.0381 (3) | −0.0451 (4) | 0.0420 (11) | |
C1 | 1.4140 (5) | 0.2653 (3) | 0.2057 (4) | 0.0468 (12) | |
C3 | 1.3865 (4) | 0.3508 (3) | 0.0593 (4) | 0.0483 (12) | |
H3 | 1.304507 | 0.347972 | 0.059573 | 0.058* | |
C21 | 0.7885 (4) | 0.0969 (3) | 0.0520 (4) | 0.0448 (12) | |
H21A | 0.737459 | 0.067720 | 0.091111 | 0.054* | |
H21B | 0.748845 | 0.143823 | 0.033801 | 0.054* | |
C33 | 0.9025 (5) | 0.5371 (3) | −0.1911 (4) | 0.0531 (13) | |
H33 | 0.887536 | 0.582779 | −0.223495 | 0.064* | |
C20 | 0.9048 (4) | 0.1122 (3) | 0.1135 (4) | 0.0448 (12) | |
H20A | 0.890051 | 0.141031 | 0.172389 | 0.054* | |
H20B | 0.940845 | 0.065073 | 0.136009 | 0.054* | |
C36 | 0.9718 (5) | 0.3300 (3) | −0.0336 (4) | 0.0488 (12) | |
C30 | 0.9468 (4) | 0.4014 (3) | −0.0914 (3) | 0.0403 (11) | |
O37 | 1.0771 (4) | 0.3190 (2) | 0.0050 (3) | 0.0713 (12) | |
C22 | 0.7064 (4) | 0.0219 (3) | −0.0900 (4) | 0.0416 (11) | |
C8 | 1.6594 (5) | 0.2749 (3) | 0.2031 (5) | 0.0619 (16) | |
H8 | 1.741262 | 0.275027 | 0.201289 | 0.074* | |
C13 | 1.1112 (5) | 0.1994 (3) | 0.2123 (4) | 0.0504 (13) | |
H13 | 1.071498 | 0.165327 | 0.255675 | 0.060* | |
C2 | 1.4604 (4) | 0.3092 (3) | 0.1298 (4) | 0.0447 (12) | |
C15 | 1.1094 (4) | 0.1619 (3) | 0.1104 (4) | 0.0441 (11) | |
H15A | 1.159126 | 0.190637 | 0.069669 | 0.053* | |
H15B | 1.143879 | 0.112331 | 0.119514 | 0.053* | |
C32 | 1.0153 (5) | 0.5195 (3) | −0.1524 (4) | 0.0461 (12) | |
C23 | 0.6608 (5) | 0.0441 (3) | −0.1847 (4) | 0.0512 (13) | |
H23 | 0.696017 | 0.083725 | −0.215779 | 0.061* | |
C35 | 0.8316 (5) | 0.4201 (3) | −0.1323 (4) | 0.0496 (12) | |
H35 | 0.769057 | 0.387250 | −0.125887 | 0.060* | |
C7 | 1.5849 (4) | 0.3126 (3) | 0.1276 (4) | 0.0484 (13) | |
C25 | 0.5121 (5) | −0.0504 (3) | −0.1898 (5) | 0.0606 (15) | |
H25 | 0.447331 | −0.074856 | −0.223319 | 0.073* | |
C6 | 1.6301 (5) | 0.3572 (3) | 0.0527 (4) | 0.0567 (14) | |
H6 | 1.711552 | 0.358731 | 0.048581 | 0.068* | |
C34 | 0.8109 (5) | 0.4877 (3) | −0.1824 (4) | 0.0553 (14) | |
H34 | 0.734703 | 0.499631 | −0.210291 | 0.066* | |
C4 | 1.4335 (5) | 0.3949 (3) | −0.0091 (4) | 0.0574 (14) | |
H4 | 1.383767 | 0.423563 | −0.053477 | 0.069* | |
C10 | 1.4877 (5) | 0.2325 (3) | 0.2808 (5) | 0.0610 (15) | |
H10 | 1.456952 | 0.206636 | 0.332558 | 0.073* | |
C5 | 1.5570 (5) | 0.3977 (4) | −0.0131 (4) | 0.0586 (15) | |
H5 | 1.588618 | 0.427256 | −0.060967 | 0.070* | |
C26 | 0.5556 (5) | −0.0741 (3) | −0.0945 (4) | 0.0523 (13) | |
H26 | 0.519734 | −0.113745 | −0.064152 | 0.063* | |
C24 | 0.5625 (5) | 0.0080 (3) | −0.2348 (4) | 0.0587 (14) | |
H24 | 0.531976 | 0.023796 | −0.298294 | 0.070* | |
C9 | 1.6110 (6) | 0.2391 (3) | 0.2775 (5) | 0.0691 (18) | |
H9 | 1.661276 | 0.217700 | 0.328940 | 0.083* | |
C12 | 1.2376 (5) | 0.2085 (3) | 0.2586 (4) | 0.0567 (14) | |
H12A | 1.239084 | 0.227295 | 0.326580 | 0.068* | |
H12B | 1.278785 | 0.160747 | 0.260277 | 0.068* | |
C29 | 0.6518 (6) | −0.1199 (3) | 0.0963 (5) | 0.0702 (17) | |
H29A | 0.652442 | −0.164217 | 0.055765 | 0.105* | |
H29B | 0.571341 | −0.107093 | 0.105865 | 0.105* | |
H29C | 0.695684 | −0.128907 | 0.160175 | 0.105* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N19 | 0.045 (2) | 0.0304 (19) | 0.042 (2) | −0.0054 (17) | 0.0080 (17) | 0.0020 (16) |
O11 | 0.045 (2) | 0.059 (2) | 0.061 (2) | −0.0112 (17) | −0.0024 (17) | 0.0140 (18) |
N16 | 0.043 (2) | 0.036 (2) | 0.038 (2) | −0.0081 (17) | 0.0053 (17) | 0.0014 (16) |
O38 | 0.061 (2) | 0.042 (2) | 0.079 (3) | −0.0071 (18) | 0.011 (2) | 0.0092 (19) |
O14 | 0.076 (3) | 0.048 (2) | 0.060 (2) | −0.003 (2) | 0.010 (2) | −0.0065 (18) |
O28 | 0.053 (2) | 0.050 (2) | 0.057 (2) | −0.0132 (17) | −0.0001 (17) | 0.0145 (17) |
O40 | 0.045 (2) | 0.079 (3) | 0.071 (3) | −0.006 (2) | −0.0013 (18) | 0.021 (2) |
C31 | 0.041 (3) | 0.049 (3) | 0.038 (3) | −0.002 (2) | 0.001 (2) | 0.000 (2) |
O39 | 0.074 (3) | 0.071 (3) | 0.068 (3) | −0.032 (2) | −0.006 (2) | 0.020 (2) |
C17 | 0.055 (3) | 0.050 (3) | 0.041 (3) | −0.011 (2) | 0.007 (2) | 0.001 (2) |
C18 | 0.050 (3) | 0.042 (3) | 0.044 (3) | −0.006 (2) | 0.015 (2) | −0.003 (2) |
C27 | 0.038 (3) | 0.037 (2) | 0.050 (3) | −0.002 (2) | 0.004 (2) | 0.000 (2) |
C1 | 0.047 (3) | 0.036 (3) | 0.055 (3) | −0.001 (2) | −0.008 (2) | −0.003 (2) |
C3 | 0.037 (3) | 0.057 (3) | 0.050 (3) | −0.002 (2) | 0.001 (2) | −0.001 (2) |
C21 | 0.045 (3) | 0.044 (3) | 0.047 (3) | −0.007 (2) | 0.013 (2) | −0.001 (2) |
C33 | 0.068 (4) | 0.043 (3) | 0.046 (3) | −0.001 (3) | 0.000 (3) | 0.004 (2) |
C20 | 0.049 (3) | 0.046 (3) | 0.040 (3) | −0.017 (2) | 0.009 (2) | 0.000 (2) |
C36 | 0.054 (3) | 0.042 (3) | 0.052 (3) | 0.005 (2) | 0.013 (2) | 0.002 (2) |
C30 | 0.048 (3) | 0.036 (2) | 0.037 (2) | −0.003 (2) | 0.008 (2) | −0.001 (2) |
O37 | 0.055 (3) | 0.065 (3) | 0.092 (3) | 0.002 (2) | −0.003 (2) | 0.029 (2) |
C22 | 0.044 (3) | 0.035 (2) | 0.046 (3) | 0.001 (2) | 0.004 (2) | −0.001 (2) |
C8 | 0.048 (3) | 0.045 (3) | 0.089 (4) | 0.006 (3) | −0.013 (3) | −0.012 (3) |
C13 | 0.056 (3) | 0.047 (3) | 0.048 (3) | −0.010 (2) | 0.008 (2) | 0.003 (2) |
C2 | 0.042 (3) | 0.039 (3) | 0.052 (3) | −0.002 (2) | −0.004 (2) | −0.008 (2) |
C15 | 0.040 (3) | 0.040 (3) | 0.053 (3) | −0.003 (2) | 0.005 (2) | 0.002 (2) |
C32 | 0.055 (3) | 0.044 (3) | 0.039 (3) | −0.010 (2) | 0.002 (2) | 0.000 (2) |
C23 | 0.060 (3) | 0.042 (3) | 0.051 (3) | −0.004 (2) | 0.001 (2) | 0.002 (2) |
C35 | 0.045 (3) | 0.048 (3) | 0.056 (3) | −0.001 (2) | 0.004 (2) | −0.004 (2) |
C7 | 0.037 (3) | 0.043 (3) | 0.063 (3) | 0.002 (2) | −0.004 (2) | −0.019 (2) |
C25 | 0.052 (3) | 0.051 (3) | 0.075 (4) | −0.002 (3) | −0.012 (3) | −0.012 (3) |
C6 | 0.041 (3) | 0.064 (4) | 0.067 (4) | −0.004 (3) | 0.009 (3) | −0.019 (3) |
C34 | 0.045 (3) | 0.063 (4) | 0.057 (3) | 0.004 (3) | 0.000 (2) | 0.000 (3) |
C4 | 0.044 (3) | 0.072 (4) | 0.056 (3) | −0.003 (3) | 0.003 (2) | 0.004 (3) |
C10 | 0.065 (4) | 0.044 (3) | 0.069 (4) | 0.001 (3) | −0.013 (3) | 0.008 (3) |
C5 | 0.047 (3) | 0.076 (4) | 0.054 (3) | −0.006 (3) | 0.009 (3) | −0.001 (3) |
C26 | 0.044 (3) | 0.042 (3) | 0.070 (4) | −0.009 (2) | 0.005 (3) | −0.003 (3) |
C24 | 0.061 (4) | 0.057 (3) | 0.055 (3) | 0.001 (3) | −0.008 (3) | −0.002 (3) |
C9 | 0.062 (4) | 0.045 (3) | 0.095 (5) | 0.008 (3) | −0.025 (3) | 0.004 (3) |
C12 | 0.061 (3) | 0.054 (3) | 0.053 (3) | −0.015 (3) | −0.005 (3) | 0.013 (3) |
C29 | 0.082 (4) | 0.059 (4) | 0.069 (4) | −0.019 (3) | 0.006 (3) | 0.019 (3) |
N19—C15 | 1.490 (6) | C3—C2 | 1.409 (7) |
N19—C20 | 1.499 (6) | C21—C20 | 1.507 (7) |
N19—C18 | 1.501 (6) | C33—C32 | 1.367 (7) |
O11—C1 | 1.359 (6) | C33—C34 | 1.375 (8) |
O11—C12 | 1.440 (6) | C36—O37 | 1.266 (6) |
N16—C22 | 1.429 (6) | C36—C30 | 1.502 (7) |
N16—C21 | 1.460 (6) | C30—C35 | 1.404 (7) |
N16—C17 | 1.462 (6) | C22—C23 | 1.380 (7) |
O38—C36 | 1.245 (6) | C8—C9 | 1.347 (9) |
O14—C13 | 1.395 (6) | C8—C7 | 1.420 (8) |
O28—C27 | 1.370 (6) | C13—C12 | 1.511 (7) |
O28—C29 | 1.424 (6) | C13—C15 | 1.519 (7) |
O40—C31 | 1.331 (6) | C2—C7 | 1.415 (7) |
C31—C30 | 1.371 (7) | C23—C24 | 1.397 (7) |
C31—C32 | 1.413 (7) | C35—C34 | 1.388 (8) |
O39—C32 | 1.353 (6) | C7—C6 | 1.417 (8) |
C17—C18 | 1.507 (7) | C25—C24 | 1.358 (8) |
C27—C26 | 1.388 (7) | C25—C26 | 1.387 (8) |
C27—C22 | 1.394 (7) | C6—C5 | 1.355 (8) |
C1—C10 | 1.373 (7) | C4—C5 | 1.407 (7) |
C1—C2 | 1.425 (7) | C10—C9 | 1.406 (9) |
C3—C4 | 1.357 (7) | ||
C15—N19—C20 | 112.4 (4) | C23—C22—C27 | 118.7 (5) |
C15—N19—C18 | 109.0 (4) | C23—C22—N16 | 122.4 (4) |
C20—N19—C18 | 110.6 (3) | C27—C22—N16 | 118.9 (4) |
C1—O11—C12 | 118.8 (4) | C9—C8—C7 | 119.7 (6) |
C22—N16—C21 | 114.7 (4) | O14—C13—C12 | 112.8 (5) |
C22—N16—C17 | 115.8 (4) | O14—C13—C15 | 112.0 (4) |
C21—N16—C17 | 108.8 (4) | C12—C13—C15 | 110.0 (5) |
C27—O28—C29 | 117.8 (4) | C3—C2—C7 | 119.3 (5) |
O40—C31—C30 | 123.8 (5) | C3—C2—C1 | 122.1 (5) |
O40—C31—C32 | 115.7 (4) | C7—C2—C1 | 118.6 (5) |
C30—C31—C32 | 120.5 (5) | N19—C15—C13 | 114.5 (4) |
N16—C17—C18 | 109.6 (4) | O39—C32—C33 | 121.6 (5) |
N19—C18—C17 | 111.3 (4) | O39—C32—C31 | 118.6 (5) |
O28—C27—C26 | 123.3 (4) | C33—C32—C31 | 119.8 (5) |
O28—C27—C22 | 116.3 (4) | C22—C23—C24 | 121.1 (5) |
C26—C27—C22 | 120.5 (5) | C34—C35—C30 | 120.0 (5) |
O11—C1—C10 | 124.8 (5) | C2—C7—C6 | 118.1 (5) |
O11—C1—C2 | 114.0 (4) | C2—C7—C8 | 119.1 (5) |
C10—C1—C2 | 121.1 (5) | C6—C7—C8 | 122.7 (5) |
C4—C3—C2 | 120.8 (5) | C24—C25—C26 | 121.1 (5) |
N16—C21—C20 | 109.8 (4) | C5—C6—C7 | 121.3 (5) |
C32—C33—C34 | 120.3 (5) | C33—C34—C35 | 120.4 (5) |
N19—C20—C21 | 111.9 (4) | C3—C4—C5 | 120.4 (5) |
O38—C36—O37 | 122.7 (5) | C1—C10—C9 | 118.3 (6) |
O38—C36—C30 | 119.7 (5) | C6—C5—C4 | 120.1 (5) |
O37—C36—C30 | 117.6 (5) | C25—C26—C27 | 119.3 (5) |
C31—C30—C35 | 119.0 (5) | C25—C24—C23 | 119.4 (5) |
C31—C30—C36 | 119.4 (5) | C8—C9—C10 | 122.8 (6) |
C35—C30—C36 | 121.6 (4) | O11—C12—C13 | 106.7 (4) |
C31H34N2O7 | F(000) = 1160 |
Mr = 546.60 | Dx = 1.348 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.843 (4) Å | Cell parameters from 9935 reflections |
b = 17.862 (6) Å | θ = 2.6–28.7° |
c = 13.913 (6) Å | µ = 0.10 mm−1 |
β = 91.715 (12)° | T = 100 K |
V = 2693.4 (17) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.15 × 0.1 mm |
Bruker APEX-II CCD diffractometer | 5449 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.068 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0687 before and 0.0635 after correction. The Ratio of minimum to maximum transmission is 0.9208. The λ/2 correction factor is Not present. | θmax = 28.7°, θmin = 2.2° |
Tmin = 0.687, Tmax = 0.746 | h = −14→14 |
66674 measured reflections | k = −24→24 |
6923 independent reflections | l = −18→18 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.054P)2 + 2.0027P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
6923 reflections | Δρmax = 0.81 e Å−3 |
365 parameters | Δρmin = −0.35 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.78792 (11) | 0.24196 (7) | 0.68502 (9) | 0.0281 (3) | |
O2 | 0.18570 (11) | 0.55245 (7) | 0.54054 (9) | 0.0253 (3) | |
O3 | 0.53323 (11) | 0.22077 (6) | 0.66879 (9) | 0.0229 (2) | |
H3 | 0.556398 | 0.206977 | 0.616091 | 0.034* | |
O4 | 0.59831 (12) | 0.17125 (7) | 0.49800 (10) | 0.0303 (3) | |
O5 | 0.35849 (11) | −0.09645 (7) | 0.25446 (9) | 0.0247 (3) | |
H5 | 0.400050 | −0.132226 | 0.273213 | 0.037* | |
O6 | 0.65744 (12) | 0.04020 (8) | 0.44000 (10) | 0.0324 (3) | |
H6 | 0.665603 | 0.080031 | 0.468782 | 0.049* | |
O7 | 0.42103 (13) | 0.22317 (7) | 0.44634 (10) | 0.0324 (3) | |
N1 | 0.49095 (12) | 0.34605 (7) | 0.54002 (10) | 0.0199 (3) | |
H1 | 0.465492 | 0.296245 | 0.517536 | 0.024* | |
N2 | 0.31513 (12) | 0.44707 (8) | 0.45110 (10) | 0.0196 (3) | |
C1 | 1.1114 (4) | 0.1067 (3) | 0.5128 (3) | 0.117 (2) | |
H1A | 1.155768 | 0.077686 | 0.470445 | 0.140* | |
C2 | 0.9825 (4) | 0.1100 (2) | 0.5023 (2) | 0.0857 (12) | |
H2 | 0.941647 | 0.082739 | 0.454130 | 0.103* | |
C3 | 0.9168 (2) | 0.15414 (16) | 0.56402 (17) | 0.0542 (7) | |
H3A | 0.831695 | 0.158344 | 0.555389 | 0.065* | |
C4 | 0.97712 (18) | 0.19285 (13) | 0.63989 (18) | 0.0427 (6) | |
C5 | 0.91096 (16) | 0.23519 (11) | 0.70841 (16) | 0.0328 (4) | |
C6 | 0.71060 (17) | 0.28322 (10) | 0.74637 (13) | 0.0269 (4) | |
H6A | 0.746003 | 0.332005 | 0.760498 | 0.032* | |
H6B | 0.700069 | 0.256686 | 0.806402 | 0.032* | |
C7 | 0.58747 (16) | 0.29138 (9) | 0.69200 (12) | 0.0229 (3) | |
H7 | 0.531025 | 0.318521 | 0.733275 | 0.027* | |
C8 | 0.60496 (15) | 0.33771 (9) | 0.60175 (12) | 0.0223 (3) | |
H8A | 0.634076 | 0.387106 | 0.620453 | 0.027* | |
H8B | 0.668430 | 0.314510 | 0.564121 | 0.027* | |
C9 | 0.52026 (15) | 0.39260 (9) | 0.45414 (12) | 0.0216 (3) | |
H9A | 0.579939 | 0.366441 | 0.415889 | 0.026* | |
H9B | 0.557000 | 0.439500 | 0.475397 | 0.026* | |
C10 | 0.40586 (15) | 0.40861 (9) | 0.39284 (12) | 0.0221 (3) | |
H10A | 0.426916 | 0.439748 | 0.338618 | 0.027* | |
H10B | 0.371331 | 0.362088 | 0.368174 | 0.027* | |
C11 | 0.21587 (15) | 0.48270 (9) | 0.39946 (12) | 0.0209 (3) | |
C12 | 0.14866 (15) | 0.53866 (9) | 0.44772 (12) | 0.0212 (3) | |
C13 | 0.12152 (17) | 0.60970 (10) | 0.59098 (14) | 0.0295 (4) | |
H13A | 0.128310 | 0.656292 | 0.557167 | 0.044* | |
H13B | 0.157144 | 0.614910 | 0.654633 | 0.044* | |
H13C | 0.036100 | 0.596254 | 0.594960 | 0.044* | |
C14 | 0.05393 (15) | 0.57689 (9) | 0.39887 (14) | 0.0254 (4) | |
H14 | 0.009945 | 0.613732 | 0.430357 | 0.030* | |
C15 | 0.02482 (17) | 0.56017 (10) | 0.30304 (14) | 0.0289 (4) | |
H15 | −0.038901 | 0.585658 | 0.271001 | 0.035* | |
C16 | 0.09007 (18) | 0.50597 (11) | 0.25540 (14) | 0.0307 (4) | |
H16 | 0.070450 | 0.494871 | 0.191454 | 0.037* | |
C17 | 0.18594 (17) | 0.46783 (10) | 0.30394 (13) | 0.0262 (4) | |
H17 | 0.230393 | 0.431787 | 0.271391 | 0.031* | |
C18 | 0.38704 (15) | 0.37948 (9) | 0.59444 (12) | 0.0226 (3) | |
H18A | 0.415241 | 0.425032 | 0.626033 | 0.027* | |
H18B | 0.362042 | 0.344655 | 0.643684 | 0.027* | |
C19 | 0.27738 (15) | 0.39715 (9) | 0.52842 (12) | 0.0221 (3) | |
H19A | 0.244148 | 0.351149 | 0.501117 | 0.027* | |
H19B | 0.213277 | 0.420940 | 0.564796 | 0.027* | |
C20 | 1.1725 (3) | 0.1450 (3) | 0.5834 (4) | 0.1040 (19) | |
H20 | 1.258179 | 0.142951 | 0.587575 | 0.125* | |
C21 | 1.1078 (2) | 0.18858 (17) | 0.6517 (3) | 0.0685 (10) | |
C22 | 1.1665 (2) | 0.22310 (17) | 0.7317 (3) | 0.0832 (13) | |
H22 | 1.252071 | 0.222316 | 0.738425 | 0.100* | |
C23 | 1.0984 (3) | 0.25752 (14) | 0.7989 (3) | 0.0711 (11) | |
H23 | 1.138054 | 0.276977 | 0.853618 | 0.085* | |
C24 | 0.9678 (2) | 0.26473 (12) | 0.7882 (2) | 0.0459 (6) | |
H24 | 0.922606 | 0.289014 | 0.834672 | 0.055* | |
C25 | 0.49626 (16) | 0.16953 (10) | 0.44910 (12) | 0.0244 (3) | |
C26 | 0.46527 (15) | 0.09957 (9) | 0.39537 (12) | 0.0215 (3) | |
C27 | 0.35123 (16) | 0.09289 (9) | 0.34577 (12) | 0.0246 (3) | |
H27 | 0.297847 | 0.133647 | 0.343934 | 0.030* | |
C28 | 0.31599 (16) | 0.02759 (10) | 0.29964 (12) | 0.0239 (3) | |
H28 | 0.239732 | 0.024237 | 0.267515 | 0.029* | |
C29 | 0.39668 (15) | −0.03341 (9) | 0.30195 (11) | 0.0199 (3) | |
C30 | 0.54544 (15) | 0.03781 (9) | 0.39586 (12) | 0.0215 (3) | |
C31 | 0.51070 (15) | −0.02821 (9) | 0.34886 (12) | 0.0220 (3) | |
H31 | 0.564318 | −0.068846 | 0.349054 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0199 (6) | 0.0323 (7) | 0.0321 (7) | 0.0022 (5) | 0.0008 (5) | −0.0022 (5) |
O2 | 0.0221 (6) | 0.0242 (6) | 0.0296 (6) | 0.0046 (5) | 0.0012 (5) | −0.0080 (5) |
O3 | 0.0253 (6) | 0.0200 (6) | 0.0236 (6) | −0.0002 (4) | 0.0039 (5) | −0.0014 (5) |
O4 | 0.0292 (6) | 0.0292 (7) | 0.0326 (7) | −0.0026 (5) | 0.0031 (5) | −0.0087 (5) |
O5 | 0.0299 (6) | 0.0206 (6) | 0.0235 (6) | 0.0002 (5) | −0.0034 (5) | −0.0029 (5) |
O6 | 0.0245 (6) | 0.0357 (7) | 0.0367 (7) | 0.0042 (5) | −0.0031 (5) | −0.0124 (6) |
O7 | 0.0418 (8) | 0.0184 (6) | 0.0368 (7) | 0.0025 (5) | −0.0015 (6) | −0.0034 (5) |
N1 | 0.0210 (6) | 0.0150 (6) | 0.0238 (7) | 0.0020 (5) | 0.0051 (5) | −0.0003 (5) |
N2 | 0.0199 (6) | 0.0185 (6) | 0.0205 (6) | 0.0017 (5) | 0.0046 (5) | −0.0001 (5) |
C1 | 0.106 (3) | 0.154 (4) | 0.095 (3) | 0.099 (3) | 0.074 (3) | 0.069 (3) |
C2 | 0.101 (3) | 0.107 (3) | 0.0506 (16) | 0.068 (2) | 0.0362 (16) | 0.0189 (17) |
C3 | 0.0509 (14) | 0.0726 (17) | 0.0402 (12) | 0.0352 (13) | 0.0198 (11) | 0.0145 (12) |
C4 | 0.0261 (9) | 0.0495 (13) | 0.0533 (13) | 0.0110 (9) | 0.0131 (9) | 0.0308 (11) |
C5 | 0.0215 (8) | 0.0274 (9) | 0.0493 (12) | −0.0034 (7) | −0.0021 (8) | 0.0184 (8) |
C6 | 0.0309 (9) | 0.0239 (8) | 0.0259 (8) | 0.0004 (7) | 0.0002 (7) | −0.0037 (7) |
C7 | 0.0266 (8) | 0.0183 (7) | 0.0242 (8) | 0.0018 (6) | 0.0051 (6) | −0.0019 (6) |
C8 | 0.0216 (8) | 0.0192 (7) | 0.0264 (8) | −0.0002 (6) | 0.0035 (6) | −0.0001 (6) |
C9 | 0.0228 (8) | 0.0178 (7) | 0.0247 (8) | 0.0012 (6) | 0.0086 (6) | 0.0008 (6) |
C10 | 0.0250 (8) | 0.0200 (7) | 0.0218 (8) | 0.0023 (6) | 0.0070 (6) | −0.0007 (6) |
C11 | 0.0198 (7) | 0.0169 (7) | 0.0259 (8) | −0.0014 (6) | 0.0025 (6) | 0.0018 (6) |
C12 | 0.0190 (7) | 0.0185 (7) | 0.0263 (8) | −0.0026 (6) | 0.0020 (6) | −0.0004 (6) |
C13 | 0.0255 (8) | 0.0257 (9) | 0.0375 (10) | 0.0043 (7) | 0.0049 (7) | −0.0101 (7) |
C14 | 0.0209 (8) | 0.0180 (7) | 0.0374 (9) | −0.0008 (6) | 0.0025 (7) | 0.0035 (7) |
C15 | 0.0250 (8) | 0.0257 (9) | 0.0359 (10) | −0.0022 (7) | −0.0028 (7) | 0.0094 (7) |
C16 | 0.0336 (10) | 0.0327 (10) | 0.0256 (9) | −0.0031 (8) | −0.0024 (7) | 0.0051 (7) |
C17 | 0.0286 (8) | 0.0245 (8) | 0.0258 (8) | −0.0004 (7) | 0.0031 (7) | −0.0013 (7) |
C18 | 0.0235 (8) | 0.0222 (8) | 0.0224 (8) | 0.0034 (6) | 0.0081 (6) | 0.0007 (6) |
C19 | 0.0217 (7) | 0.0203 (8) | 0.0246 (8) | 0.0019 (6) | 0.0069 (6) | 0.0014 (6) |
C20 | 0.0481 (17) | 0.126 (3) | 0.141 (4) | 0.055 (2) | 0.058 (2) | 0.100 (3) |
C21 | 0.0234 (10) | 0.0696 (18) | 0.113 (3) | 0.0141 (11) | 0.0183 (13) | 0.0669 (18) |
C22 | 0.0216 (11) | 0.0559 (17) | 0.171 (4) | −0.0056 (11) | −0.0143 (17) | 0.072 (2) |
C23 | 0.0466 (15) | 0.0345 (12) | 0.129 (3) | −0.0198 (11) | −0.0449 (18) | 0.0408 (16) |
C24 | 0.0409 (12) | 0.0260 (10) | 0.0694 (16) | −0.0118 (8) | −0.0242 (11) | 0.0179 (10) |
C25 | 0.0305 (9) | 0.0215 (8) | 0.0216 (8) | −0.0032 (6) | 0.0061 (7) | −0.0005 (6) |
C26 | 0.0271 (8) | 0.0196 (7) | 0.0182 (7) | −0.0012 (6) | 0.0055 (6) | −0.0002 (6) |
C27 | 0.0296 (9) | 0.0204 (8) | 0.0239 (8) | 0.0052 (6) | 0.0023 (7) | 0.0022 (6) |
C28 | 0.0241 (8) | 0.0250 (8) | 0.0225 (8) | 0.0018 (6) | −0.0017 (6) | 0.0029 (6) |
C29 | 0.0248 (8) | 0.0190 (7) | 0.0161 (7) | −0.0014 (6) | 0.0033 (6) | 0.0001 (6) |
C30 | 0.0194 (7) | 0.0263 (8) | 0.0189 (7) | −0.0009 (6) | 0.0045 (6) | −0.0032 (6) |
C31 | 0.0224 (8) | 0.0215 (8) | 0.0224 (8) | 0.0038 (6) | 0.0032 (6) | −0.0028 (6) |
O1—C5 | 1.369 (2) | C10—H10A | 0.9700 |
O1—C6 | 1.420 (2) | C10—H10B | 0.9700 |
O2—C12 | 1.363 (2) | C11—C17 | 1.384 (2) |
O2—C13 | 1.432 (2) | C11—C12 | 1.418 (2) |
O3—C7 | 1.425 (2) | C12—C14 | 1.393 (2) |
O3—H3 | 0.8200 | C13—H13A | 0.9600 |
O4—C25 | 1.282 (2) | C13—H13B | 0.9600 |
O5—C29 | 1.364 (2) | C13—H13C | 0.9600 |
O5—H5 | 0.8200 | C14—C15 | 1.393 (3) |
O6—C30 | 1.345 (2) | C14—H14 | 0.9300 |
O6—H6 | 0.8200 | C15—C16 | 1.380 (3) |
O7—C25 | 1.258 (2) | C15—H15 | 0.9300 |
N1—C8 | 1.491 (2) | C16—C17 | 1.400 (3) |
N1—C9 | 1.498 (2) | C16—H16 | 0.9300 |
N1—C18 | 1.500 (2) | C17—H17 | 0.9300 |
N1—H1 | 0.9800 | C18—C19 | 1.514 (2) |
N2—C11 | 1.426 (2) | C18—H18A | 0.9700 |
N2—C10 | 1.464 (2) | C18—H18B | 0.9700 |
N2—C19 | 1.465 (2) | C19—H19A | 0.9700 |
C1—C20 | 1.354 (7) | C19—H19B | 0.9700 |
C1—C2 | 1.402 (6) | C20—C21 | 1.428 (6) |
C1—H1A | 0.9300 | C20—H20 | 0.9300 |
C2—C3 | 1.379 (3) | C21—C22 | 1.408 (5) |
C2—H2 | 0.9300 | C22—C23 | 1.357 (6) |
C3—C4 | 1.407 (4) | C22—H22 | 0.9300 |
C3—H3A | 0.9300 | C23—C24 | 1.425 (4) |
C4—C21 | 1.423 (3) | C23—H23 | 0.9300 |
C4—C5 | 1.427 (3) | C24—H24 | 0.9300 |
C5—C24 | 1.361 (3) | C25—C26 | 1.490 (2) |
C6—C7 | 1.522 (2) | C26—C27 | 1.403 (2) |
C6—H6A | 0.9700 | C26—C30 | 1.404 (2) |
C6—H6B | 0.9700 | C27—C28 | 1.380 (2) |
C7—C8 | 1.521 (2) | C27—H27 | 0.9300 |
C7—H7 | 0.9800 | C28—C29 | 1.397 (2) |
C8—H8A | 0.9700 | C28—H28 | 0.9300 |
C8—H8B | 0.9700 | C29—C31 | 1.384 (2) |
C9—C10 | 1.511 (2) | C30—C31 | 1.395 (2) |
C9—H9A | 0.9700 | C31—H31 | 0.9300 |
C9—H9B | 0.9700 | ||
C5—O1—C6 | 119.44 (15) | O2—C13—H13B | 109.5 |
C12—O2—C13 | 117.35 (14) | H13A—C13—H13B | 109.5 |
C7—O3—H3 | 109.5 | O2—C13—H13C | 109.5 |
C29—O5—H5 | 109.5 | H13A—C13—H13C | 109.5 |
C30—O6—H6 | 109.5 | H13B—C13—H13C | 109.5 |
C8—N1—C9 | 108.83 (12) | C15—C14—C12 | 120.28 (17) |
C8—N1—C18 | 111.79 (13) | C15—C14—H14 | 119.9 |
C9—N1—C18 | 111.24 (12) | C12—C14—H14 | 119.9 |
C8—N1—H1 | 108.3 | C16—C15—C14 | 120.34 (17) |
C9—N1—H1 | 108.3 | C16—C15—H15 | 119.8 |
C18—N1—H1 | 108.3 | C14—C15—H15 | 119.8 |
C11—N2—C10 | 116.10 (13) | C15—C16—C17 | 119.59 (17) |
C11—N2—C19 | 114.73 (13) | C15—C16—H16 | 120.2 |
C10—N2—C19 | 109.15 (13) | C17—C16—H16 | 120.2 |
C20—C1—C2 | 121.3 (3) | C11—C17—C16 | 121.28 (17) |
C20—C1—H1A | 119.4 | C11—C17—H17 | 119.4 |
C2—C1—H1A | 119.4 | C16—C17—H17 | 119.4 |
C3—C2—C1 | 119.4 (4) | N1—C18—C19 | 111.40 (14) |
C3—C2—H2 | 120.3 | N1—C18—H18A | 109.3 |
C1—C2—H2 | 120.3 | C19—C18—H18A | 109.3 |
C2—C3—C4 | 120.7 (3) | N1—C18—H18B | 109.3 |
C2—C3—H3A | 119.6 | C19—C18—H18B | 109.3 |
C4—C3—H3A | 119.6 | H18A—C18—H18B | 108.0 |
C3—C4—C21 | 119.9 (3) | N2—C19—C18 | 109.92 (13) |
C3—C4—C5 | 122.01 (18) | N2—C19—H19A | 109.7 |
C21—C4—C5 | 118.0 (3) | C18—C19—H19A | 109.7 |
C24—C5—O1 | 125.1 (2) | N2—C19—H19B | 109.7 |
C24—C5—C4 | 121.8 (2) | C18—C19—H19B | 109.7 |
O1—C5—C4 | 113.19 (19) | H19A—C19—H19B | 108.2 |
O1—C6—C7 | 106.01 (14) | C1—C20—C21 | 121.2 (3) |
O1—C6—H6A | 110.5 | C1—C20—H20 | 119.4 |
C7—C6—H6A | 110.5 | C21—C20—H20 | 119.4 |
O1—C6—H6B | 110.5 | C22—C21—C4 | 119.5 (3) |
C7—C6—H6B | 110.5 | C22—C21—C20 | 123.0 (3) |
H6A—C6—H6B | 108.7 | C4—C21—C20 | 117.4 (4) |
O3—C7—C8 | 110.83 (14) | C23—C22—C21 | 120.1 (2) |
O3—C7—C6 | 112.21 (14) | C23—C22—H22 | 120.0 |
C8—C7—C6 | 109.48 (14) | C21—C22—H22 | 120.0 |
O3—C7—H7 | 108.1 | C22—C23—C24 | 121.9 (3) |
C8—C7—H7 | 108.1 | C22—C23—H23 | 119.0 |
C6—C7—H7 | 108.1 | C24—C23—H23 | 119.0 |
N1—C8—C7 | 114.09 (13) | C5—C24—C23 | 118.3 (3) |
N1—C8—H8A | 108.7 | C5—C24—H24 | 120.8 |
C7—C8—H8A | 108.7 | C23—C24—H24 | 120.8 |
N1—C8—H8B | 108.7 | O7—C25—O4 | 123.13 (16) |
C7—C8—H8B | 108.7 | O7—C25—C26 | 119.16 (16) |
H8A—C8—H8B | 107.6 | O4—C25—C26 | 117.69 (15) |
N1—C9—C10 | 111.41 (13) | C27—C26—C30 | 118.16 (15) |
N1—C9—H9A | 109.3 | C27—C26—C25 | 120.03 (15) |
C10—C9—H9A | 109.3 | C30—C26—C25 | 121.76 (15) |
N1—C9—H9B | 109.3 | C28—C27—C26 | 121.90 (16) |
C10—C9—H9B | 109.3 | C28—C27—H27 | 119.0 |
H9A—C9—H9B | 108.0 | C26—C27—H27 | 119.0 |
N2—C10—C9 | 109.27 (14) | C27—C28—C29 | 118.95 (16) |
N2—C10—H10A | 109.8 | C27—C28—H28 | 120.5 |
C9—C10—H10A | 109.8 | C29—C28—H28 | 120.5 |
N2—C10—H10B | 109.8 | O5—C29—C31 | 122.55 (15) |
C9—C10—H10B | 109.8 | O5—C29—C28 | 116.87 (15) |
H10A—C10—H10B | 108.3 | C31—C29—C28 | 120.56 (15) |
C17—C11—C12 | 118.74 (15) | O6—C30—C31 | 117.93 (15) |
C17—C11—N2 | 123.35 (15) | O6—C30—C26 | 121.84 (15) |
C12—C11—N2 | 117.83 (15) | C31—C30—C26 | 120.22 (15) |
O2—C12—C14 | 124.44 (15) | C29—C31—C30 | 120.19 (15) |
O2—C12—C11 | 115.78 (14) | C29—C31—H31 | 119.9 |
C14—C12—C11 | 119.76 (16) | C30—C31—H31 | 119.9 |
O2—C13—H13A | 109.5 | ||
C20—C1—C2—C3 | 1.1 (6) | N2—C11—C17—C16 | −177.95 (16) |
C1—C2—C3—C4 | −3.0 (5) | C15—C16—C17—C11 | 0.8 (3) |
C2—C3—C4—C21 | 2.0 (4) | C8—N1—C18—C19 | 172.53 (13) |
C2—C3—C4—C5 | −176.1 (2) | C9—N1—C18—C19 | 50.63 (18) |
C6—O1—C5—C24 | 0.7 (3) | C11—N2—C19—C18 | −164.66 (13) |
C6—O1—C5—C4 | −179.51 (16) | C10—N2—C19—C18 | 63.07 (17) |
C3—C4—C5—C24 | 171.7 (2) | N1—C18—C19—N2 | −56.49 (17) |
C21—C4—C5—C24 | −6.5 (3) | C2—C1—C20—C21 | 1.8 (6) |
C3—C4—C5—O1 | −8.1 (3) | C3—C4—C21—C22 | −175.5 (2) |
C21—C4—C5—O1 | 173.75 (17) | C5—C4—C21—C22 | 2.6 (3) |
C5—O1—C6—C7 | 170.36 (14) | C3—C4—C21—C20 | 0.9 (3) |
O1—C6—C7—O3 | 59.42 (18) | C5—C4—C21—C20 | 179.0 (2) |
O1—C6—C7—C8 | −64.07 (17) | C1—C20—C21—C22 | 173.5 (3) |
C9—N1—C8—C7 | 179.93 (13) | C1—C20—C21—C4 | −2.8 (4) |
C18—N1—C8—C7 | 56.66 (18) | C4—C21—C22—C23 | 2.7 (3) |
O3—C7—C8—N1 | 52.74 (18) | C20—C21—C22—C23 | −173.5 (2) |
C6—C7—C8—N1 | 177.03 (13) | C21—C22—C23—C24 | −4.5 (4) |
C8—N1—C9—C10 | −175.21 (13) | O1—C5—C24—C23 | −175.43 (18) |
C18—N1—C9—C10 | −51.61 (17) | C4—C5—C24—C23 | 4.8 (3) |
C11—N2—C10—C9 | 164.75 (13) | C22—C23—C24—C5 | 0.8 (3) |
C19—N2—C10—C9 | −63.70 (17) | O7—C25—C26—C27 | −2.6 (2) |
N1—C9—C10—N2 | 58.15 (17) | O4—C25—C26—C27 | 175.89 (15) |
C10—N2—C11—C17 | 16.0 (2) | O7—C25—C26—C30 | −179.91 (16) |
C19—N2—C11—C17 | −112.91 (18) | O4—C25—C26—C30 | −1.4 (2) |
C10—N2—C11—C12 | −160.97 (14) | C30—C26—C27—C28 | 1.1 (2) |
C19—N2—C11—C12 | 70.14 (18) | C25—C26—C27—C28 | −176.29 (16) |
C13—O2—C12—C14 | 0.7 (2) | C26—C27—C28—C29 | −0.4 (3) |
C13—O2—C12—C11 | 178.78 (14) | C27—C28—C29—O5 | −179.28 (15) |
C17—C11—C12—O2 | −177.70 (15) | C27—C28—C29—C31 | −0.7 (2) |
N2—C11—C12—O2 | −0.6 (2) | C27—C26—C30—O6 | 178.58 (15) |
C17—C11—C12—C14 | 0.5 (2) | C25—C26—C30—O6 | −4.1 (2) |
N2—C11—C12—C14 | 177.61 (14) | C27—C26—C30—C31 | −0.7 (2) |
O2—C12—C14—C15 | 178.27 (15) | C25—C26—C30—C31 | 176.66 (15) |
C11—C12—C14—C15 | 0.2 (2) | O5—C29—C31—C30 | 179.61 (15) |
C12—C14—C15—C16 | −0.5 (3) | C28—C29—C31—C30 | 1.1 (2) |
C14—C15—C16—C17 | 0.0 (3) | O6—C30—C31—C29 | −179.68 (15) |
C12—C11—C17—C16 | −1.0 (3) | C26—C30—C31—C29 | −0.4 (2) |
C62H67N4O14 | F(000) = 1158 |
Mr = 1092.19 | Dx = 1.316 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.4733 (3) Å | Cell parameters from 4614 reflections |
b = 17.6286 (5) Å | θ = 3.7–24.4° |
c = 13.6530 (4) Å | µ = 0.09 mm−1 |
β = 93.290 (2)° | T = 293 K |
V = 2756.89 (13) Å3 | Block, colourless |
Z = 2 | 0.2 × 0.2 × 0.1 mm |
SuperNova, Dual, Cu at zero, Eos diffractometer | 6342 reflections with I > 2σ(I) |
ω scans | Rint = 0.049 |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 25.0°, θmin = 3.0° |
Tmin = 0.530, Tmax = 1.000 | h = −13→11 |
11695 measured reflections | k = −19→20 |
8293 independent reflections | l = −14→16 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.061 | w = 1/[σ2(Fo2) + (0.0705P)2 + 0.6067P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.170 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.21 e Å−3 |
8293 reflections | Δρmin = −0.19 e Å−3 |
729 parameters | Absolute structure: Flack x determined using 1864 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
1 restraint | Absolute structure parameter: −2.6 (10) |
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 | ||
N19 | 0.4378 (4) | 0.5031 (3) | 0.2998 (3) | 0.0444 (10) | |
H19 | 0.416330 | 0.555730 | 0.284061 | 0.053* | |
N16 | 0.2568 (4) | 0.4084 (3) | 0.2140 (3) | 0.0471 (11) | |
N45 | 0.6262 (4) | 0.2902 (3) | 0.2884 (3) | 0.0507 (11) | |
O57 | 0.7376 (4) | 0.4057 (2) | 0.2035 (3) | 0.0634 (11) | |
O14 | 0.5110 (4) | 0.6210 (2) | 0.4355 (3) | 0.0623 (11) | |
H14 | 0.537467 | 0.638531 | 0.385777 | 0.093* | |
C18 | 0.4500 (5) | 0.4613 (3) | 0.2058 (4) | 0.0495 (13) | |
H18A | 0.486620 | 0.412563 | 0.219637 | 0.059* | |
H18B | 0.500263 | 0.489872 | 0.164534 | 0.059* | |
N48 | 0.4486 (4) | 0.1921 (3) | 0.2011 (4) | 0.0549 (12) | |
H48 | 0.480657 | 0.141370 | 0.214157 | 0.066* | |
O28 | 0.1523 (4) | 0.2982 (3) | 0.3086 (3) | 0.0726 (13) | |
O11 | 0.7496 (3) | 0.5847 (3) | 0.4383 (3) | 0.0634 (11) | |
C17 | 0.3335 (5) | 0.4489 (4) | 0.1514 (4) | 0.0529 (14) | |
H17A | 0.299065 | 0.497370 | 0.132627 | 0.064* | |
H17B | 0.343893 | 0.419805 | 0.092238 | 0.064* | |
C22 | 0.1557 (5) | 0.3727 (3) | 0.1670 (4) | 0.0503 (13) | |
O43 | 0.3941 (5) | 0.0788 (3) | 0.0540 (3) | 0.0747 (13) | |
H43 | 0.367779 | 0.048732 | 0.092827 | 0.112* | |
C49 | 0.4385 (6) | 0.2303 (4) | 0.2973 (4) | 0.0630 (17) | |
H49A | 0.392217 | 0.198849 | 0.338592 | 0.076* | |
H49B | 0.398063 | 0.278187 | 0.287157 | 0.076* | |
C46 | 0.6459 (5) | 0.2487 (4) | 0.1975 (4) | 0.0554 (15) | |
H46A | 0.684524 | 0.200960 | 0.213436 | 0.066* | |
H46B | 0.696614 | 0.278206 | 0.157665 | 0.066* | |
C47 | 0.5329 (5) | 0.2337 (4) | 0.1408 (4) | 0.0579 (15) | |
H47A | 0.547681 | 0.203981 | 0.083069 | 0.069* | |
H47B | 0.498601 | 0.281577 | 0.119065 | 0.069* | |
C13 | 0.5540 (5) | 0.5472 (4) | 0.4512 (4) | 0.0529 (14) | |
H13 | 0.501491 | 0.521105 | 0.494208 | 0.064* | |
C51 | 0.7288 (5) | 0.3214 (3) | 0.3363 (4) | 0.0560 (15) | |
C27 | 0.1027 (5) | 0.3142 (4) | 0.2178 (5) | 0.0542 (14) | |
C50 | 0.5548 (6) | 0.2446 (4) | 0.3488 (4) | 0.0625 (16) | |
H50A | 0.544290 | 0.270512 | 0.410300 | 0.075* | |
H50B | 0.593445 | 0.196627 | 0.363337 | 0.075* | |
C42 | 0.3270 (6) | 0.1461 (4) | 0.0522 (5) | 0.0686 (17) | |
H42 | 0.361691 | 0.181680 | 0.007005 | 0.082* | |
C21 | 0.2333 (5) | 0.4567 (4) | 0.2982 (4) | 0.0541 (14) | |
H21A | 0.176533 | 0.432274 | 0.337780 | 0.065* | |
H21B | 0.201235 | 0.504842 | 0.275329 | 0.065* | |
C44 | 0.3308 (6) | 0.1826 (4) | 0.1524 (5) | 0.0664 (17) | |
H44A | 0.294276 | 0.232070 | 0.146291 | 0.080* | |
H44B | 0.284357 | 0.152089 | 0.194654 | 0.080* | |
C20 | 0.3442 (5) | 0.4695 (4) | 0.3584 (4) | 0.0526 (14) | |
H20A | 0.371514 | 0.421597 | 0.385989 | 0.063* | |
H20B | 0.329159 | 0.503277 | 0.412302 | 0.063* | |
C15 | 0.5539 (5) | 0.5035 (3) | 0.3562 (4) | 0.0498 (13) | |
H15A | 0.611664 | 0.525467 | 0.315441 | 0.060* | |
H15B | 0.577004 | 0.451578 | 0.370492 | 0.060* | |
C1 | 0.8662 (5) | 0.5890 (3) | 0.4640 (4) | 0.0544 (14) | |
O40 | 0.1549 (5) | 0.0777 (3) | 0.0774 (4) | 0.0866 (15) | |
C52 | 0.7851 (5) | 0.3815 (4) | 0.2920 (5) | 0.0570 (15) | |
C23 | 0.1142 (5) | 0.3906 (4) | 0.0729 (4) | 0.0631 (16) | |
H23 | 0.149574 | 0.428818 | 0.038324 | 0.076* | |
C12 | 0.6753 (6) | 0.5459 (4) | 0.5009 (4) | 0.0658 (17) | |
H12A | 0.675508 | 0.570888 | 0.564199 | 0.079* | |
H12B | 0.701497 | 0.494001 | 0.510867 | 0.079* | |
C25 | −0.0345 (6) | 0.2958 (4) | 0.0808 (6) | 0.079 (2) | |
H25 | −0.099094 | 0.270577 | 0.052242 | 0.095* | |
C30 | 0.0373 (6) | 0.0664 (4) | 0.0779 (5) | 0.0690 (18) | |
C31 | 0.0047 (6) | 0.0091 (4) | 0.1438 (5) | 0.0660 (17) | |
C2 | 0.9311 (5) | 0.6259 (3) | 0.3943 (4) | 0.0558 (15) | |
C56 | 0.7732 (7) | 0.2971 (5) | 0.4268 (5) | 0.078 (2) | |
H56 | 0.737910 | 0.256549 | 0.457218 | 0.094* | |
C26 | 0.0070 (5) | 0.2772 (4) | 0.1740 (6) | 0.0690 (18) | |
H26 | −0.029740 | 0.239334 | 0.208226 | 0.083* | |
C24 | 0.0190 (6) | 0.3512 (5) | 0.0300 (6) | 0.079 (2) | |
H24 | −0.008108 | 0.362802 | −0.033752 | 0.095* | |
C3 | 0.8796 (5) | 0.6598 (4) | 0.3076 (5) | 0.0638 (17) | |
H3 | 0.799188 | 0.656686 | 0.295053 | 0.077* | |
C10 | 0.9177 (6) | 0.5593 (4) | 0.5481 (5) | 0.0656 (17) | |
H10 | 0.872627 | 0.535782 | 0.593775 | 0.079* | |
C55 | 0.8705 (8) | 0.3323 (6) | 0.4739 (6) | 0.089 (2) | |
H55 | 0.898102 | 0.316149 | 0.535848 | 0.107* | |
C7 | 1.0546 (6) | 0.6317 (4) | 0.4117 (5) | 0.0678 (18) | |
C53 | 0.8832 (6) | 0.4149 (4) | 0.3383 (6) | 0.0716 (19) | |
H53 | 0.921230 | 0.454337 | 0.307962 | 0.086* | |
C36 | −0.1154 (6) | −0.0055 (4) | 0.1538 (5) | 0.0694 (18) | |
C6 | 1.1185 (6) | 0.6696 (5) | 0.3414 (7) | 0.080 (2) | |
H6 | 1.199229 | 0.673081 | 0.351329 | 0.096* | |
C39 | −0.0464 (7) | 0.1062 (4) | 0.0236 (6) | 0.081 (2) | |
H39 | −0.025204 | 0.142152 | −0.021929 | 0.097* | |
C37 | −0.1995 (7) | 0.0394 (5) | 0.0995 (6) | 0.083 (2) | |
H37 | −0.278704 | 0.032167 | 0.107379 | 0.100* | |
C33 | 0.0539 (7) | −0.0919 (5) | 0.2566 (5) | 0.083 (2) | |
H33 | 0.110196 | −0.120954 | 0.290955 | 0.100* | |
C4 | 0.9444 (6) | 0.6964 (5) | 0.2431 (5) | 0.078 (2) | |
H4 | 0.908533 | 0.718619 | 0.187438 | 0.094* | |
C9 | 1.0394 (7) | 0.5644 (4) | 0.5648 (6) | 0.082 (2) | |
H9 | 1.074994 | 0.543847 | 0.621689 | 0.098* | |
C35 | −0.1460 (7) | −0.0662 (5) | 0.2162 (5) | 0.080 (2) | |
H35 | −0.224417 | −0.077331 | 0.222501 | 0.096* | |
C8 | 1.1053 (7) | 0.5991 (5) | 0.4989 (7) | 0.086 (2) | |
H8 | 1.185756 | 0.601619 | 0.511225 | 0.103* | |
C38 | −0.1644 (8) | 0.0916 (5) | 0.0377 (7) | 0.089 (2) | |
H38 | −0.220684 | 0.119841 | 0.002154 | 0.107* | |
C32 | 0.0866 (6) | −0.0348 (4) | 0.1978 (5) | 0.0715 (19) | |
H32 | 0.165635 | −0.024583 | 0.193258 | 0.086* | |
C34 | −0.0656 (7) | −0.1072 (5) | 0.2655 (5) | 0.082 (2) | |
H34 | −0.088071 | −0.146185 | 0.306181 | 0.098* | |
C54 | 0.9239 (7) | 0.3894 (5) | 0.4293 (6) | 0.086 (2) | |
H54 | 0.989177 | 0.412150 | 0.460373 | 0.103* | |
C5 | 1.0663 (7) | 0.7011 (5) | 0.2601 (7) | 0.089 (2) | |
H5 | 1.110973 | 0.725921 | 0.215242 | 0.107* | |
C59 | 0.5258 (5) | 0.2480 (3) | 0.8586 (4) | 0.0434 (12) | |
O67 | 0.4234 (4) | 0.1563 (3) | 0.7613 (3) | 0.0698 (13) | |
O78 | 0.6261 (4) | 0.5036 (3) | 0.7631 (3) | 0.0718 (12) | |
C70 | 0.4828 (5) | 0.4370 (3) | 0.6660 (4) | 0.0469 (12) | |
C65 | 0.5199 (5) | 0.1773 (3) | 0.8010 (4) | 0.0505 (13) | |
O66 | 0.6127 (4) | 0.1399 (2) | 0.7907 (3) | 0.0645 (11) | |
O79 | 0.6616 (4) | 0.3714 (3) | 0.6990 (3) | 0.0721 (12) | |
H79 | 0.691795 | 0.330154 | 0.688944 | 0.108* | |
O69 | 0.7322 (4) | 0.2364 (3) | 0.8928 (4) | 0.0718 (13) | |
H69 | 0.720743 | 0.199660 | 0.856804 | 0.108* | |
C71 | 0.3709 (5) | 0.4358 (4) | 0.6202 (4) | 0.0549 (14) | |
O77 | 0.4591 (4) | 0.5612 (3) | 0.7262 (4) | 0.0759 (13) | |
C60 | 0.6318 (5) | 0.2755 (3) | 0.8992 (4) | 0.0499 (13) | |
C75 | 0.5518 (5) | 0.3723 (4) | 0.6579 (4) | 0.0511 (14) | |
O80 | 0.3025 (4) | 0.4984 (3) | 0.6170 (4) | 0.0820 (14) | |
H80 | 0.321527 | 0.526133 | 0.663407 | 0.123* | |
O68 | 0.3194 (4) | 0.2687 (3) | 0.8329 (4) | 0.0774 (14) | |
H68 | 0.327742 | 0.233317 | 0.794990 | 0.116* | |
C76 | 0.5254 (6) | 0.5045 (4) | 0.7218 (4) | 0.0560 (14) | |
C64 | 0.4248 (5) | 0.2924 (3) | 0.8692 (4) | 0.0480 (13) | |
C74 | 0.5102 (6) | 0.3082 (4) | 0.6102 (4) | 0.0601 (15) | |
H74 | 0.557478 | 0.265583 | 0.605899 | 0.072* | |
C63 | 0.4316 (6) | 0.3607 (4) | 0.9186 (4) | 0.0640 (17) | |
H63 | 0.364691 | 0.389381 | 0.926042 | 0.077* | |
C73 | 0.3996 (6) | 0.3077 (4) | 0.5693 (4) | 0.0658 (17) | |
H73 | 0.371413 | 0.264218 | 0.537610 | 0.079* | |
C62 | 0.5379 (6) | 0.3859 (4) | 0.9568 (4) | 0.0630 (17) | |
H62 | 0.542112 | 0.432320 | 0.989156 | 0.076* | |
C72 | 0.3276 (6) | 0.3707 (4) | 0.5738 (4) | 0.0655 (17) | |
H72 | 0.251547 | 0.369337 | 0.546286 | 0.079* | |
C61 | 0.6374 (6) | 0.3449 (4) | 0.9486 (4) | 0.0598 (16) | |
H61 | 0.708342 | 0.362950 | 0.975533 | 0.072* | |
C58 | 0.7904 (7) | 0.4677 (4) | 0.1568 (6) | 0.084 (2) | |
H58A | 0.791964 | 0.511013 | 0.199544 | 0.125* | |
H58B | 0.746215 | 0.479690 | 0.096962 | 0.125* | |
H58C | 0.868723 | 0.454468 | 0.142365 | 0.125* | |
C41 | 0.2003 (6) | 0.1342 (4) | 0.0174 (5) | 0.0726 (19) | |
H41 | 0.160216 | 0.159503 | −0.033945 | 0.087* | |
C29 | 0.1094 (7) | 0.2331 (5) | 0.3591 (6) | 0.092 (2) | |
H29A | 0.154942 | 0.225920 | 0.419530 | 0.138* | |
H29B | 0.115464 | 0.188936 | 0.318597 | 0.138* | |
H29C | 0.029160 | 0.241156 | 0.372705 | 0.138* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N19 | 0.056 (3) | 0.031 (2) | 0.047 (2) | −0.004 (2) | 0.0106 (19) | 0.0041 (19) |
N16 | 0.056 (3) | 0.039 (3) | 0.047 (2) | −0.010 (2) | 0.0100 (19) | 0.000 (2) |
N45 | 0.064 (3) | 0.041 (3) | 0.048 (3) | −0.003 (2) | 0.013 (2) | 0.000 (2) |
O57 | 0.069 (3) | 0.050 (3) | 0.072 (3) | −0.015 (2) | 0.008 (2) | 0.003 (2) |
O14 | 0.079 (3) | 0.046 (3) | 0.062 (3) | 0.002 (2) | 0.010 (2) | −0.0001 (19) |
C18 | 0.053 (3) | 0.045 (4) | 0.051 (3) | −0.003 (3) | 0.014 (2) | −0.003 (2) |
N48 | 0.068 (3) | 0.032 (3) | 0.066 (3) | −0.009 (2) | 0.015 (2) | 0.000 (2) |
O28 | 0.074 (3) | 0.059 (3) | 0.086 (3) | −0.016 (2) | 0.015 (2) | 0.023 (2) |
O11 | 0.061 (2) | 0.073 (3) | 0.056 (2) | −0.010 (2) | −0.0060 (18) | 0.015 (2) |
C17 | 0.067 (4) | 0.044 (4) | 0.049 (3) | −0.011 (3) | 0.011 (2) | 0.000 (3) |
C22 | 0.052 (3) | 0.038 (3) | 0.062 (3) | −0.005 (3) | 0.007 (2) | −0.005 (3) |
O43 | 0.104 (4) | 0.053 (3) | 0.068 (3) | 0.007 (3) | 0.009 (2) | −0.007 (2) |
C49 | 0.083 (4) | 0.044 (4) | 0.065 (4) | −0.009 (3) | 0.030 (3) | −0.007 (3) |
C46 | 0.072 (4) | 0.042 (4) | 0.053 (3) | −0.005 (3) | 0.016 (3) | −0.006 (3) |
C47 | 0.080 (4) | 0.038 (3) | 0.057 (3) | −0.015 (3) | 0.016 (3) | −0.003 (3) |
C13 | 0.061 (3) | 0.047 (4) | 0.052 (3) | −0.010 (3) | 0.003 (2) | 0.011 (3) |
C51 | 0.073 (4) | 0.040 (3) | 0.055 (4) | 0.003 (3) | 0.005 (3) | −0.005 (3) |
C27 | 0.055 (3) | 0.040 (4) | 0.069 (4) | 0.000 (3) | 0.010 (3) | 0.001 (3) |
C50 | 0.085 (5) | 0.050 (4) | 0.055 (4) | −0.012 (3) | 0.021 (3) | −0.003 (3) |
C42 | 0.094 (5) | 0.046 (4) | 0.066 (4) | 0.002 (4) | 0.012 (3) | 0.003 (3) |
C21 | 0.058 (3) | 0.046 (4) | 0.060 (3) | −0.006 (3) | 0.018 (3) | −0.002 (3) |
C44 | 0.072 (4) | 0.046 (4) | 0.081 (4) | −0.008 (3) | 0.006 (3) | −0.004 (3) |
C20 | 0.063 (4) | 0.047 (4) | 0.050 (3) | −0.010 (3) | 0.020 (3) | −0.003 (3) |
C15 | 0.051 (3) | 0.042 (3) | 0.057 (3) | −0.004 (3) | 0.003 (2) | 0.004 (3) |
C1 | 0.060 (4) | 0.041 (4) | 0.061 (3) | 0.002 (3) | −0.008 (3) | −0.003 (3) |
O40 | 0.090 (4) | 0.070 (4) | 0.098 (4) | −0.019 (3) | −0.009 (3) | 0.033 (3) |
C52 | 0.063 (4) | 0.042 (4) | 0.066 (4) | 0.003 (3) | 0.007 (3) | −0.010 (3) |
C23 | 0.071 (4) | 0.058 (4) | 0.059 (4) | 0.001 (3) | −0.001 (3) | 0.001 (3) |
C12 | 0.084 (4) | 0.064 (5) | 0.049 (3) | −0.014 (4) | −0.003 (3) | 0.008 (3) |
C25 | 0.063 (4) | 0.062 (5) | 0.111 (6) | −0.002 (4) | −0.009 (4) | −0.024 (5) |
C30 | 0.077 (5) | 0.050 (4) | 0.077 (4) | −0.010 (3) | −0.012 (3) | 0.003 (3) |
C31 | 0.083 (5) | 0.048 (4) | 0.065 (4) | −0.011 (3) | −0.008 (3) | −0.008 (3) |
C2 | 0.058 (3) | 0.044 (4) | 0.064 (4) | 0.000 (3) | −0.002 (3) | −0.014 (3) |
C56 | 0.103 (5) | 0.065 (5) | 0.065 (4) | −0.003 (4) | −0.003 (4) | −0.002 (4) |
C26 | 0.058 (4) | 0.044 (4) | 0.106 (6) | −0.004 (3) | 0.016 (4) | −0.004 (4) |
C24 | 0.079 (5) | 0.072 (5) | 0.083 (5) | −0.009 (4) | −0.009 (4) | −0.006 (4) |
C3 | 0.057 (4) | 0.065 (5) | 0.069 (4) | −0.003 (3) | 0.000 (3) | −0.005 (3) |
C10 | 0.075 (4) | 0.053 (4) | 0.067 (4) | 0.003 (3) | −0.015 (3) | −0.002 (3) |
C55 | 0.102 (6) | 0.087 (7) | 0.077 (5) | 0.012 (5) | −0.020 (4) | −0.011 (5) |
C7 | 0.059 (4) | 0.050 (4) | 0.094 (5) | 0.011 (3) | −0.002 (3) | −0.018 (4) |
C53 | 0.067 (4) | 0.053 (4) | 0.094 (5) | −0.006 (3) | 0.001 (4) | −0.023 (4) |
C36 | 0.075 (4) | 0.066 (5) | 0.066 (4) | −0.010 (4) | −0.006 (3) | −0.024 (4) |
C6 | 0.051 (4) | 0.073 (5) | 0.117 (7) | −0.001 (3) | 0.010 (4) | −0.012 (5) |
C39 | 0.108 (6) | 0.049 (4) | 0.083 (5) | −0.001 (4) | −0.016 (4) | 0.002 (4) |
C37 | 0.078 (5) | 0.070 (6) | 0.100 (6) | −0.002 (4) | −0.007 (4) | −0.024 (5) |
C33 | 0.098 (6) | 0.074 (5) | 0.076 (5) | −0.024 (4) | −0.009 (4) | 0.025 (4) |
C4 | 0.081 (5) | 0.089 (6) | 0.066 (4) | −0.003 (4) | 0.011 (4) | −0.003 (4) |
C9 | 0.086 (5) | 0.059 (5) | 0.096 (5) | 0.011 (4) | −0.038 (4) | −0.001 (4) |
C35 | 0.089 (5) | 0.079 (6) | 0.072 (4) | −0.034 (5) | 0.013 (4) | −0.020 (4) |
C8 | 0.060 (4) | 0.064 (5) | 0.132 (7) | 0.008 (4) | −0.029 (4) | −0.001 (5) |
C38 | 0.103 (6) | 0.056 (5) | 0.104 (6) | 0.004 (4) | −0.034 (5) | −0.009 (4) |
C32 | 0.066 (4) | 0.070 (5) | 0.077 (4) | −0.020 (3) | −0.012 (3) | 0.016 (4) |
C34 | 0.097 (6) | 0.081 (6) | 0.065 (4) | −0.030 (5) | 0.001 (4) | 0.011 (4) |
C54 | 0.082 (5) | 0.076 (6) | 0.098 (6) | 0.006 (4) | −0.014 (4) | −0.032 (5) |
C5 | 0.079 (5) | 0.087 (6) | 0.104 (6) | −0.011 (4) | 0.033 (5) | −0.002 (5) |
C59 | 0.057 (3) | 0.037 (3) | 0.037 (3) | 0.005 (2) | 0.006 (2) | 0.003 (2) |
O67 | 0.069 (3) | 0.065 (3) | 0.075 (3) | −0.001 (2) | −0.003 (2) | −0.028 (2) |
O78 | 0.078 (3) | 0.063 (3) | 0.073 (3) | −0.001 (2) | −0.007 (2) | −0.018 (2) |
C70 | 0.062 (3) | 0.037 (3) | 0.041 (3) | 0.003 (3) | 0.009 (2) | 0.006 (2) |
C65 | 0.061 (4) | 0.044 (3) | 0.046 (3) | 0.000 (3) | 0.003 (3) | −0.005 (2) |
O66 | 0.066 (3) | 0.046 (3) | 0.081 (3) | 0.011 (2) | 0.003 (2) | −0.020 (2) |
O79 | 0.071 (3) | 0.065 (3) | 0.079 (3) | 0.015 (2) | −0.003 (2) | −0.005 (3) |
O69 | 0.054 (2) | 0.073 (4) | 0.088 (3) | 0.006 (2) | −0.001 (2) | −0.019 (3) |
C71 | 0.064 (4) | 0.049 (4) | 0.052 (3) | −0.001 (3) | 0.009 (3) | 0.010 (3) |
O77 | 0.092 (3) | 0.037 (3) | 0.099 (3) | 0.010 (2) | 0.005 (3) | −0.005 (2) |
C60 | 0.063 (4) | 0.042 (3) | 0.045 (3) | −0.001 (3) | 0.011 (2) | 0.001 (2) |
C75 | 0.062 (3) | 0.051 (4) | 0.041 (3) | 0.001 (3) | 0.009 (2) | 0.006 (3) |
O80 | 0.073 (3) | 0.067 (4) | 0.105 (4) | 0.017 (3) | −0.003 (3) | 0.019 (3) |
O68 | 0.062 (3) | 0.090 (4) | 0.079 (3) | 0.018 (2) | −0.005 (2) | −0.034 (3) |
C76 | 0.075 (4) | 0.044 (4) | 0.050 (3) | −0.001 (3) | 0.009 (3) | 0.003 (3) |
C64 | 0.060 (3) | 0.046 (3) | 0.039 (3) | 0.007 (3) | 0.003 (2) | 0.000 (2) |
C74 | 0.082 (4) | 0.043 (4) | 0.056 (3) | 0.002 (3) | 0.008 (3) | −0.009 (3) |
C63 | 0.090 (5) | 0.054 (4) | 0.048 (3) | 0.025 (4) | 0.003 (3) | −0.009 (3) |
C73 | 0.095 (5) | 0.055 (4) | 0.047 (3) | −0.015 (4) | 0.005 (3) | −0.003 (3) |
C62 | 0.101 (5) | 0.040 (4) | 0.050 (3) | −0.002 (3) | 0.011 (3) | −0.011 (3) |
C72 | 0.067 (4) | 0.073 (5) | 0.055 (4) | −0.015 (4) | 0.000 (3) | 0.015 (3) |
C61 | 0.074 (4) | 0.053 (4) | 0.054 (3) | −0.012 (3) | 0.012 (3) | −0.010 (3) |
C58 | 0.100 (6) | 0.062 (5) | 0.090 (5) | −0.028 (4) | 0.016 (4) | 0.004 (4) |
C41 | 0.090 (5) | 0.060 (5) | 0.067 (4) | −0.008 (4) | −0.008 (3) | 0.020 (3) |
C29 | 0.098 (6) | 0.068 (6) | 0.113 (6) | −0.013 (4) | 0.036 (5) | 0.030 (5) |
N19—C18 | 1.495 (7) | C31—C32 | 1.395 (9) |
N19—C20 | 1.496 (6) | C31—C36 | 1.416 (9) |
N19—C15 | 1.500 (7) | C2—C3 | 1.425 (9) |
N16—C22 | 1.438 (7) | C2—C7 | 1.427 (8) |
N16—C17 | 1.449 (7) | C56—C55 | 1.402 (11) |
N16—C21 | 1.468 (7) | C3—C4 | 1.349 (9) |
N45—C51 | 1.424 (7) | C10—C9 | 1.405 (10) |
N45—C50 | 1.441 (7) | C55—C54 | 1.343 (12) |
N45—C46 | 1.469 (7) | C7—C6 | 1.409 (11) |
O57—C52 | 1.366 (7) | C7—C8 | 1.417 (11) |
O57—C58 | 1.418 (8) | C53—C54 | 1.378 (11) |
O14—C13 | 1.402 (8) | C36—C37 | 1.422 (11) |
C18—C17 | 1.507 (8) | C36—C35 | 1.424 (11) |
N48—C44 | 1.481 (8) | C6—C5 | 1.350 (11) |
N48—C49 | 1.486 (7) | C39—C38 | 1.403 (11) |
N48—C47 | 1.498 (7) | C37—C38 | 1.327 (11) |
O28—C27 | 1.362 (7) | C33—C32 | 1.353 (9) |
O28—C29 | 1.440 (8) | C33—C34 | 1.410 (10) |
O11—C1 | 1.365 (7) | C4—C5 | 1.407 (11) |
O11—C12 | 1.417 (7) | C9—C8 | 1.354 (11) |
C22—C23 | 1.380 (8) | C35—C34 | 1.325 (11) |
C22—C27 | 1.401 (8) | C59—C60 | 1.394 (8) |
O43—C42 | 1.414 (8) | C59—C64 | 1.414 (7) |
C49—C50 | 1.492 (9) | C59—C65 | 1.474 (8) |
C46—C47 | 1.495 (8) | O67—C65 | 1.259 (7) |
C13—C15 | 1.508 (8) | O78—C76 | 1.256 (7) |
C13—C12 | 1.513 (8) | C70—C71 | 1.395 (8) |
C51—C56 | 1.378 (9) | C70—C75 | 1.397 (8) |
C51—C52 | 1.396 (9) | C70—C76 | 1.481 (9) |
C27—C26 | 1.382 (9) | C65—O66 | 1.267 (7) |
C42—C44 | 1.509 (9) | O79—C75 | 1.350 (7) |
C42—C41 | 1.518 (9) | O69—C60 | 1.349 (7) |
C21—C20 | 1.493 (8) | C71—O80 | 1.354 (8) |
C1—C10 | 1.366 (8) | C71—C72 | 1.389 (9) |
C1—C2 | 1.401 (9) | O77—C76 | 1.260 (8) |
O40—C30 | 1.365 (8) | C60—C61 | 1.397 (8) |
O40—C41 | 1.408 (8) | C75—C74 | 1.376 (9) |
C52—C53 | 1.391 (9) | O68—C64 | 1.347 (7) |
C23—C24 | 1.394 (9) | C64—C63 | 1.379 (9) |
C25—C24 | 1.365 (11) | C74—C73 | 1.356 (9) |
C25—C26 | 1.373 (10) | C63—C62 | 1.373 (9) |
C30—C39 | 1.371 (10) | C73—C72 | 1.387 (10) |
C30—C31 | 1.418 (9) | C62—C61 | 1.360 (9) |
C18—N19—C20 | 111.6 (4) | C3—C2—C7 | 117.9 (6) |
C18—N19—C15 | 108.6 (4) | C51—C56—C55 | 121.1 (8) |
C20—N19—C15 | 111.8 (4) | C25—C26—C27 | 120.9 (7) |
C22—N16—C17 | 117.0 (4) | C25—C24—C23 | 120.5 (7) |
C22—N16—C21 | 115.0 (4) | C4—C3—C2 | 121.7 (6) |
C17—N16—C21 | 108.7 (4) | C1—C10—C9 | 119.4 (7) |
C51—N45—C50 | 115.8 (5) | C54—C55—C56 | 119.8 (8) |
C51—N45—C46 | 114.6 (4) | C6—C7—C8 | 124.1 (7) |
C50—N45—C46 | 109.0 (5) | C6—C7—C2 | 118.2 (6) |
C52—O57—C58 | 118.7 (5) | C8—C7—C2 | 117.7 (7) |
N19—C18—C17 | 111.7 (4) | C54—C53—C52 | 119.7 (7) |
C44—N48—C49 | 109.5 (5) | C31—C36—C37 | 118.9 (7) |
C44—N48—C47 | 114.2 (5) | C31—C36—C35 | 117.9 (7) |
C49—N48—C47 | 110.5 (4) | C37—C36—C35 | 123.1 (7) |
C27—O28—C29 | 117.6 (5) | C5—C6—C7 | 122.1 (7) |
C1—O11—C12 | 119.1 (4) | C30—C39—C38 | 118.9 (8) |
N16—C17—C18 | 109.4 (5) | C38—C37—C36 | 119.7 (8) |
C23—C22—C27 | 119.5 (5) | C32—C33—C34 | 119.8 (7) |
C23—C22—N16 | 122.8 (5) | C3—C4—C5 | 120.1 (7) |
C27—C22—N16 | 117.6 (5) | C8—C9—C10 | 120.6 (7) |
N48—C49—C50 | 112.3 (5) | C34—C35—C36 | 121.7 (7) |
N45—C46—C47 | 110.7 (5) | C9—C8—C7 | 121.6 (7) |
C46—C47—N48 | 111.7 (5) | C37—C38—C39 | 123.0 (8) |
O14—C13—C15 | 111.1 (5) | C33—C32—C31 | 121.6 (7) |
O14—C13—C12 | 112.9 (5) | C35—C34—C33 | 120.3 (7) |
C15—C13—C12 | 109.4 (5) | C55—C54—C53 | 121.0 (7) |
C56—C51—C52 | 117.9 (6) | C6—C5—C4 | 120.1 (7) |
C56—C51—N45 | 123.0 (6) | C60—C59—C64 | 117.9 (5) |
C52—C51—N45 | 119.0 (5) | C60—C59—C65 | 121.3 (5) |
O28—C27—C26 | 125.2 (6) | C64—C59—C65 | 120.7 (5) |
O28—C27—C22 | 115.6 (5) | C71—C70—C75 | 117.6 (5) |
C26—C27—C22 | 119.2 (6) | C71—C70—C76 | 120.7 (5) |
N45—C50—C49 | 110.3 (5) | C75—C70—C76 | 121.6 (5) |
O43—C42—C44 | 110.7 (6) | O67—C65—O66 | 121.6 (5) |
O43—C42—C41 | 113.6 (6) | O67—C65—C59 | 119.4 (5) |
C44—C42—C41 | 108.7 (5) | O66—C65—C59 | 119.0 (5) |
N16—C21—C20 | 109.2 (4) | O80—C71—C72 | 117.8 (6) |
N48—C44—C42 | 115.7 (5) | O80—C71—C70 | 121.3 (6) |
C21—C20—N19 | 112.4 (5) | C72—C71—C70 | 120.9 (6) |
N19—C15—C13 | 113.6 (4) | O69—C60—C59 | 121.7 (5) |
O11—C1—C10 | 124.4 (6) | O69—C60—C61 | 117.5 (6) |
O11—C1—C2 | 113.8 (5) | C59—C60—C61 | 120.7 (5) |
C10—C1—C2 | 121.8 (6) | O79—C75—C74 | 118.5 (6) |
C30—O40—C41 | 120.4 (5) | O79—C75—C70 | 119.8 (5) |
O57—C52—C53 | 122.7 (6) | C74—C75—C70 | 121.7 (6) |
O57—C52—C51 | 116.8 (5) | O78—C76—O77 | 122.0 (6) |
C53—C52—C51 | 120.5 (6) | O78—C76—C70 | 119.3 (6) |
C22—C23—C24 | 119.8 (6) | O77—C76—C70 | 118.7 (6) |
O11—C12—C13 | 106.9 (5) | O68—C64—C63 | 118.4 (5) |
C24—C25—C26 | 119.9 (6) | O68—C64—C59 | 121.0 (5) |
O40—C30—C39 | 125.7 (7) | C63—C64—C59 | 120.6 (5) |
O40—C30—C31 | 113.9 (6) | C73—C74—C75 | 119.4 (6) |
C39—C30—C31 | 120.4 (7) | C62—C63—C64 | 119.5 (6) |
C32—C31—C36 | 118.6 (7) | C74—C73—C72 | 121.5 (6) |
C32—C31—C30 | 122.4 (6) | C61—C62—C63 | 121.9 (6) |
C36—C31—C30 | 118.9 (6) | C73—C72—C71 | 118.8 (6) |
C1—C2—C3 | 123.2 (5) | C62—C61—C60 | 119.3 (6) |
C1—C2—C7 | 118.9 (6) | O40—C41—C42 | 107.2 (5) |
C31H34N2O5.90 | F(000) = 1125 |
Mr = 529.00 | Dx = 1.357 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.197 (2) Å | Cell parameters from 9055 reflections |
b = 17.627 (4) Å | θ = 2.8–29.6° |
c = 13.199 (3) Å | µ = 0.09 mm−1 |
β = 96.347 (6)° | T = 100 K |
V = 2589.0 (9) Å3 | Block, colourless |
Z = 4 |
Bruker APEX-II CCD diffractometer | 6706 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.025 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0556 before and 0.0396 after correction. The Ratio of minimum to maximum transmission is 0.9175. The λ/2 correction factor is Not present. | θmax = 29.6°, θmin = 2.3° |
Tmin = 0.684, Tmax = 0.746 | h = −15→15 |
53638 measured reflections | k = −24→24 |
7114 independent reflections | l = −18→18 |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0668P)2 + 0.9174P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
7114 reflections | Δρmax = 0.44 e Å−3 |
458 parameters | Δρmin = −0.36 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.40751 (7) | 0.21223 (4) | 0.47798 (6) | 0.02155 (16) | |
O2 | 0.59958 (7) | 0.17801 (5) | 0.50816 (7) | 0.02470 (17) | |
O4 | 0.81219 (7) | 0.24191 (4) | 0.69519 (6) | 0.02155 (16) | |
O5 | 0.20250 (7) | 0.55782 (4) | 0.55389 (6) | 0.01860 (15) | |
O6 | 0.56649 (7) | 0.22997 (4) | 0.70647 (6) | 0.02179 (16) | |
N1 | 0.31212 (7) | 0.44412 (5) | 0.46293 (6) | 0.01387 (16) | |
N2 | 0.49826 (7) | 0.34488 (4) | 0.55594 (6) | 0.01303 (15) | |
C1 | 0.49214 (9) | 0.16693 (5) | 0.46845 (8) | 0.01730 (18) | |
C2 | 0.46670 (9) | 0.09485 (5) | 0.40913 (7) | 0.01550 (18) | |
C4 | 0.53321 (11) | −0.02481 (6) | 0.34337 (8) | 0.0229 (2) | |
C5 | 0.41643 (11) | −0.04171 (6) | 0.30478 (8) | 0.0230 (2) | |
C6 | 0.32349 (10) | 0.00875 (6) | 0.31730 (8) | 0.0223 (2) | |
C7 | 0.34959 (9) | 0.07621 (6) | 0.36946 (8) | 0.01873 (19) | |
C3 | 0.55976 (9) | 0.04349 (6) | 0.39543 (8) | 0.01891 (19) | 0.9 |
O3 | 0.67319 (8) | 0.05744 (6) | 0.42936 (8) | 0.0277 (2) | 0.9 |
H3 | 0.678071 | 0.099659 | 0.459047 | 0.077 (9) | 0.9 |
C3A | 0.55976 (9) | 0.04349 (6) | 0.39543 (8) | 0.01891 (19) | 0.1 |
H3A | 0.640245 | 0.055050 | 0.421357 | 0.023* | 0.1 |
C8 | 0.00489 (9) | 0.55098 (6) | 0.31066 (8) | 0.0213 (2) | |
C9 | 0.04978 (9) | 0.57337 (6) | 0.40906 (8) | 0.01920 (19) | |
C10 | 0.15012 (8) | 0.53762 (5) | 0.45938 (7) | 0.01541 (18) | |
C11 | 0.20648 (8) | 0.47759 (5) | 0.41143 (7) | 0.01446 (17) | |
C12 | 0.29302 (8) | 0.40038 (5) | 0.55455 (7) | 0.01524 (17) | |
C13 | 0.41253 (9) | 0.38526 (5) | 0.61699 (7) | 0.01518 (17) | |
C14 | 0.62179 (8) | 0.34039 (5) | 0.61173 (7) | 0.01570 (18) | |
C15 | 0.62664 (9) | 0.30082 (6) | 0.71467 (8) | 0.01800 (19) | |
C16 | 0.75723 (10) | 0.29324 (6) | 0.76001 (8) | 0.0215 (2) | |
C17 | 0.93474 (9) | 0.23602 (5) | 0.70528 (8) | 0.01844 (19) | |
C18 | 0.98030 (9) | 0.19091 (5) | 0.62838 (7) | 0.01664 (18) | |
C19 | 1.10686 (9) | 0.18526 (6) | 0.62736 (8) | 0.01844 (19) | |
C20 | 1.15202 (9) | 0.13783 (6) | 0.55361 (8) | 0.0213 (2) | |
C21 | 1.07530 (9) | 0.09643 (6) | 0.48659 (8) | 0.0213 (2) | |
C22 | 0.14789 (11) | 0.61916 (6) | 0.60282 (9) | 0.0248 (2) | |
C23 | 0.38308 (9) | 0.39801 (6) | 0.39960 (7) | 0.01596 (18) | |
C24 | 0.50647 (8) | 0.38390 (5) | 0.45591 (7) | 0.01528 (17) | |
C25 | 1.18430 (10) | 0.22328 (6) | 0.70401 (9) | 0.0233 (2) | |
C26 | 1.13662 (10) | 0.26096 (6) | 0.78075 (10) | 0.0258 (2) | |
C27 | 1.01067 (10) | 0.26802 (6) | 0.78220 (9) | 0.0235 (2) | |
C28 | 0.94947 (9) | 0.10234 (6) | 0.48750 (8) | 0.01960 (19) | |
C29 | 0.90291 (9) | 0.14962 (6) | 0.55608 (8) | 0.01816 (19) | |
C30 | 0.16001 (9) | 0.45676 (6) | 0.31326 (8) | 0.01843 (19) | |
C31 | 0.06012 (10) | 0.49319 (6) | 0.26228 (8) | 0.0214 (2) | |
H6 | 0.5935 (15) | 0.2065 (10) | 0.6508 (14) | 0.032* | |
H4 | 0.6043 (14) | −0.0586 (9) | 0.3381 (12) | 0.026* | |
H5 | 0.3962 (14) | −0.0912 (9) | 0.2708 (12) | 0.026* | |
H6A | 0.2416 (14) | −0.0054 (9) | 0.2897 (12) | 0.026* | |
H7 | 0.2881 (14) | 0.1112 (9) | 0.3784 (12) | 0.026* | |
H8 | −0.0611 (14) | 0.5774 (9) | 0.2741 (12) | 0.026* | |
H9 | 0.0091 (14) | 0.6159 (9) | 0.4411 (12) | 0.026* | |
H12A | 0.2520 (14) | 0.3511 (9) | 0.5367 (12) | 0.026* | |
H12B | 0.2444 (14) | 0.4310 (9) | 0.5956 (12) | 0.026* | |
H13A | 0.4475 (14) | 0.4312 (10) | 0.6416 (12) | 0.026* | |
H13B | 0.3991 (14) | 0.3532 (9) | 0.6758 (12) | 0.026* | |
H14A | 0.6518 (14) | 0.3927 (9) | 0.6194 (12) | 0.026* | |
H14B | 0.6699 (14) | 0.3133 (9) | 0.5670 (12) | 0.026* | |
H15 | 0.5862 (14) | 0.3309 (9) | 0.7644 (12) | 0.026* | |
H16A | 0.7975 (14) | 0.3436 (9) | 0.7606 (12) | 0.026* | |
H16B | 0.7598 (14) | 0.2720 (9) | 0.8297 (13) | 0.026* | |
H20 | 1.2400 (14) | 0.1347 (9) | 0.5514 (12) | 0.026* | |
H21 | 1.1062 (14) | 0.0644 (9) | 0.4404 (12) | 0.026* | |
H22A | 0.1503 (15) | 0.6667 (10) | 0.5607 (13) | 0.032* | |
H22B | 0.1990 (15) | 0.6270 (10) | 0.6658 (14) | 0.032* | |
H22C | 0.0625 (16) | 0.6084 (10) | 0.6116 (13) | 0.032* | |
H23A | 0.3972 (14) | 0.4269 (9) | 0.3383 (12) | 0.026* | |
H23B | 0.3425 (14) | 0.3477 (9) | 0.3803 (12) | 0.026* | |
H24A | 0.5540 (14) | 0.3511 (9) | 0.4169 (12) | 0.026* | |
H24B | 0.5505 (14) | 0.4312 (9) | 0.4714 (12) | 0.026* | |
H25 | 1.2711 (14) | 0.2206 (9) | 0.6997 (12) | 0.026* | |
H26 | 1.1874 (14) | 0.2827 (9) | 0.8353 (12) | 0.026* | |
H27 | 0.9775 (14) | 0.2935 (9) | 0.8361 (13) | 0.026* | |
H28 | 0.8994 (14) | 0.0727 (9) | 0.4411 (13) | 0.026* | |
H29 | 0.8152 (14) | 0.1527 (9) | 0.5589 (12) | 0.026* | |
H30 | 0.1994 (14) | 0.4159 (9) | 0.2823 (12) | 0.026* | |
H31 | 0.0285 (15) | 0.4778 (9) | 0.1931 (13) | 0.026* | |
H2 | 0.4683 (15) | 0.2945 (10) | 0.5382 (13) | 0.032 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0201 (3) | 0.0143 (3) | 0.0306 (4) | 0.0000 (3) | 0.0047 (3) | −0.0056 (3) |
O2 | 0.0200 (4) | 0.0236 (4) | 0.0300 (4) | 0.0000 (3) | 0.0007 (3) | −0.0087 (3) |
O4 | 0.0194 (3) | 0.0216 (4) | 0.0223 (4) | 0.0064 (3) | −0.0036 (3) | −0.0072 (3) |
O5 | 0.0202 (3) | 0.0172 (3) | 0.0182 (3) | 0.0037 (3) | 0.0011 (3) | −0.0050 (3) |
O6 | 0.0299 (4) | 0.0152 (3) | 0.0208 (4) | 0.0002 (3) | 0.0051 (3) | 0.0013 (3) |
N1 | 0.0147 (3) | 0.0140 (3) | 0.0130 (3) | 0.0026 (3) | 0.0018 (3) | 0.0005 (3) |
N2 | 0.0143 (3) | 0.0106 (3) | 0.0143 (3) | 0.0011 (3) | 0.0020 (3) | −0.0002 (3) |
C1 | 0.0210 (4) | 0.0136 (4) | 0.0181 (4) | −0.0013 (3) | 0.0054 (3) | −0.0015 (3) |
C2 | 0.0207 (4) | 0.0123 (4) | 0.0142 (4) | 0.0000 (3) | 0.0051 (3) | −0.0003 (3) |
C4 | 0.0346 (6) | 0.0179 (4) | 0.0165 (4) | 0.0095 (4) | 0.0047 (4) | −0.0002 (3) |
C5 | 0.0391 (6) | 0.0139 (4) | 0.0161 (4) | −0.0003 (4) | 0.0040 (4) | −0.0009 (3) |
C6 | 0.0278 (5) | 0.0183 (5) | 0.0209 (5) | −0.0047 (4) | 0.0040 (4) | −0.0022 (4) |
C7 | 0.0215 (4) | 0.0156 (4) | 0.0199 (4) | −0.0012 (3) | 0.0055 (3) | −0.0011 (3) |
C3 | 0.0230 (5) | 0.0188 (4) | 0.0152 (4) | 0.0047 (4) | 0.0035 (3) | 0.0004 (3) |
O3 | 0.0194 (4) | 0.0327 (5) | 0.0296 (5) | 0.0059 (4) | −0.0030 (3) | −0.0115 (4) |
H3 | 0.028 (13) | 0.059 (18) | 0.14 (3) | −0.012 (13) | −0.023 (15) | −0.019 (19) |
C3A | 0.0230 (5) | 0.0188 (4) | 0.0152 (4) | 0.0047 (4) | 0.0035 (3) | 0.0004 (3) |
C8 | 0.0188 (4) | 0.0190 (5) | 0.0251 (5) | 0.0024 (4) | −0.0022 (4) | 0.0046 (4) |
C9 | 0.0176 (4) | 0.0160 (4) | 0.0240 (5) | 0.0024 (3) | 0.0022 (4) | 0.0020 (4) |
C10 | 0.0156 (4) | 0.0134 (4) | 0.0173 (4) | −0.0004 (3) | 0.0021 (3) | 0.0001 (3) |
C11 | 0.0142 (4) | 0.0129 (4) | 0.0161 (4) | 0.0000 (3) | 0.0010 (3) | 0.0008 (3) |
C12 | 0.0157 (4) | 0.0154 (4) | 0.0151 (4) | 0.0014 (3) | 0.0037 (3) | 0.0015 (3) |
C13 | 0.0180 (4) | 0.0145 (4) | 0.0134 (4) | 0.0033 (3) | 0.0034 (3) | −0.0004 (3) |
C14 | 0.0148 (4) | 0.0136 (4) | 0.0182 (4) | 0.0013 (3) | 0.0000 (3) | 0.0004 (3) |
C15 | 0.0218 (4) | 0.0154 (4) | 0.0166 (4) | 0.0038 (3) | 0.0011 (3) | −0.0007 (3) |
C16 | 0.0253 (5) | 0.0194 (5) | 0.0185 (4) | 0.0075 (4) | −0.0032 (4) | −0.0046 (4) |
C17 | 0.0199 (4) | 0.0135 (4) | 0.0207 (5) | 0.0032 (3) | −0.0036 (3) | 0.0005 (3) |
C18 | 0.0177 (4) | 0.0136 (4) | 0.0177 (4) | 0.0009 (3) | −0.0020 (3) | 0.0029 (3) |
C19 | 0.0179 (4) | 0.0156 (4) | 0.0210 (4) | −0.0010 (3) | −0.0015 (3) | 0.0061 (3) |
C20 | 0.0171 (4) | 0.0248 (5) | 0.0219 (5) | 0.0004 (4) | 0.0023 (3) | 0.0061 (4) |
C21 | 0.0196 (4) | 0.0262 (5) | 0.0185 (4) | 0.0021 (4) | 0.0045 (3) | 0.0019 (4) |
C22 | 0.0318 (6) | 0.0198 (5) | 0.0234 (5) | 0.0075 (4) | 0.0055 (4) | −0.0054 (4) |
C23 | 0.0170 (4) | 0.0176 (4) | 0.0134 (4) | 0.0029 (3) | 0.0023 (3) | −0.0016 (3) |
C24 | 0.0164 (4) | 0.0153 (4) | 0.0146 (4) | 0.0015 (3) | 0.0039 (3) | 0.0016 (3) |
C25 | 0.0197 (5) | 0.0168 (4) | 0.0314 (5) | −0.0026 (4) | −0.0060 (4) | 0.0045 (4) |
C26 | 0.0258 (5) | 0.0160 (4) | 0.0325 (6) | −0.0011 (4) | −0.0105 (4) | −0.0021 (4) |
C27 | 0.0273 (5) | 0.0152 (4) | 0.0257 (5) | 0.0029 (4) | −0.0070 (4) | −0.0036 (4) |
C28 | 0.0185 (4) | 0.0230 (5) | 0.0170 (4) | 0.0000 (4) | 0.0009 (3) | −0.0004 (4) |
C29 | 0.0170 (4) | 0.0196 (4) | 0.0173 (4) | 0.0011 (3) | −0.0009 (3) | 0.0004 (3) |
C30 | 0.0205 (4) | 0.0166 (4) | 0.0174 (4) | 0.0011 (3) | −0.0013 (3) | −0.0014 (3) |
C31 | 0.0226 (5) | 0.0207 (5) | 0.0194 (5) | 0.0005 (4) | −0.0040 (4) | 0.0016 (4) |
O1—C1 | 1.2560 (12) | C12—H12B | 0.973 (16) |
O2—C1 | 1.2731 (13) | C13—H13A | 0.941 (17) |
O4—C17 | 1.3678 (13) | C13—H13B | 0.985 (16) |
O4—C16 | 1.4304 (12) | C14—C15 | 1.5229 (14) |
O5—C10 | 1.3656 (12) | C14—H14A | 0.982 (16) |
O5—C22 | 1.4309 (12) | C14—H14B | 0.968 (16) |
O6—C15 | 1.4174 (13) | C15—C16 | 1.5233 (14) |
O6—H6 | 0.923 (18) | C15—H15 | 0.992 (16) |
N1—C11 | 1.4252 (12) | C16—H16A | 0.996 (16) |
N1—C23 | 1.4621 (12) | C16—H16B | 0.991 (16) |
N1—C12 | 1.4696 (12) | C17—C27 | 1.3715 (14) |
N2—C14 | 1.4954 (12) | C17—C18 | 1.4274 (14) |
N2—C13 | 1.4995 (12) | C18—C29 | 1.4171 (14) |
N2—C24 | 1.5004 (12) | C18—C19 | 1.4221 (14) |
N2—H2 | 0.968 (18) | C19—C20 | 1.4181 (15) |
C1—C2 | 1.5031 (13) | C19—C25 | 1.4248 (14) |
C2—C7 | 1.3963 (14) | C20—C21 | 1.3729 (15) |
C2—C3A | 1.4070 (13) | C20—H20 | 0.991 (16) |
C2—C3 | 1.4070 (13) | C21—C28 | 1.4141 (14) |
C4—C5 | 1.3823 (17) | C21—H21 | 0.926 (16) |
C4—C3A | 1.4017 (15) | C22—H22A | 1.008 (18) |
C4—C3 | 1.4017 (15) | C22—H22B | 0.965 (18) |
C4—H4 | 1.003 (16) | C22—H22C | 0.994 (17) |
C5—C6 | 1.3926 (16) | C23—C24 | 1.5152 (13) |
C5—H5 | 0.996 (16) | C23—H23A | 0.983 (16) |
C6—C7 | 1.3888 (14) | C23—H23B | 1.016 (16) |
C6—H6A | 0.980 (16) | C24—H24A | 0.971 (16) |
C7—H7 | 0.942 (16) | C24—H24B | 0.978 (16) |
C3—O3 | 1.3222 (14) | C25—C26 | 1.3681 (18) |
O3—H3 | 0.8400 | C25—H25 | 0.981 (16) |
C3A—H3A | 0.9500 | C26—C27 | 1.4180 (16) |
C8—C31 | 1.3838 (15) | C26—H26 | 0.948 (16) |
C8—C9 | 1.3968 (15) | C27—H27 | 0.951 (17) |
C8—H8 | 0.957 (16) | C28—C29 | 1.3748 (14) |
C9—C10 | 1.3912 (13) | C28—H28 | 0.941 (17) |
C9—H9 | 0.995 (16) | C29—H29 | 0.989 (16) |
C10—C11 | 1.4166 (13) | C30—C31 | 1.3964 (14) |
C11—C30 | 1.3912 (13) | C30—H30 | 0.959 (16) |
C12—C13 | 1.5156 (13) | C31—H31 | 0.980 (16) |
C12—H12A | 0.999 (16) | ||
C17—O4—C16 | 118.89 (8) | C15—C14—H14B | 110.5 (10) |
C10—O5—C22 | 116.58 (8) | H14A—C14—H14B | 108.6 (13) |
C15—O6—H6 | 105.2 (11) | O6—C15—C14 | 111.45 (8) |
C11—N1—C23 | 115.61 (8) | O6—C15—C16 | 112.34 (8) |
C11—N1—C12 | 114.90 (7) | C14—C15—C16 | 109.19 (8) |
C23—N1—C12 | 108.45 (7) | O6—C15—H15 | 105.9 (9) |
C14—N2—C13 | 111.88 (7) | C14—C15—H15 | 111.8 (9) |
C14—N2—C24 | 108.32 (7) | C16—C15—H15 | 106.0 (9) |
C13—N2—C24 | 111.12 (7) | O4—C16—C15 | 106.16 (8) |
C14—N2—H2 | 110.3 (10) | O4—C16—H16A | 110.1 (9) |
C13—N2—H2 | 109.9 (10) | C15—C16—H16A | 109.8 (9) |
C24—N2—H2 | 105.1 (10) | O4—C16—H16B | 110.3 (9) |
O1—C1—O2 | 123.39 (9) | C15—C16—H16B | 109.0 (9) |
O1—C1—C2 | 119.20 (9) | H16A—C16—H16B | 111.3 (13) |
O2—C1—C2 | 117.40 (9) | O4—C17—C27 | 125.02 (10) |
C7—C2—C3A | 118.59 (9) | O4—C17—C18 | 113.99 (8) |
C7—C2—C3 | 118.59 (9) | C27—C17—C18 | 120.97 (10) |
C7—C2—C1 | 120.68 (9) | C29—C18—C19 | 119.58 (9) |
C3A—C2—C1 | 120.69 (9) | C29—C18—C17 | 121.66 (9) |
C3—C2—C1 | 120.69 (9) | C19—C18—C17 | 118.72 (9) |
C5—C4—C3A | 120.43 (10) | C20—C19—C18 | 118.61 (9) |
C5—C4—C3 | 120.43 (10) | C20—C19—C25 | 121.97 (10) |
C5—C4—H4 | 124.9 (9) | C18—C19—C25 | 119.29 (10) |
C3A—C4—H4 | 114.7 (9) | C21—C20—C19 | 120.70 (10) |
C3—C4—H4 | 114.7 (9) | C21—C20—H20 | 120.3 (9) |
C4—C5—C6 | 120.49 (10) | C19—C20—H20 | 119.0 (9) |
C4—C5—H5 | 120.9 (9) | C20—C21—C28 | 120.56 (10) |
C6—C5—H5 | 118.5 (9) | C20—C21—H21 | 119.7 (10) |
C7—C6—C5 | 119.12 (10) | C28—C21—H21 | 119.7 (10) |
C7—C6—H6A | 122.6 (9) | O5—C22—H22A | 109.9 (10) |
C5—C6—H6A | 118.3 (9) | O5—C22—H22B | 104.7 (10) |
C6—C7—C2 | 121.65 (10) | H22A—C22—H22B | 107.9 (14) |
C6—C7—H7 | 120.4 (10) | O5—C22—H22C | 111.9 (10) |
C2—C7—H7 | 117.9 (10) | H22A—C22—H22C | 107.9 (14) |
O3—C3—C4 | 118.01 (10) | H22B—C22—H22C | 114.4 (15) |
O3—C3—C2 | 122.28 (10) | N1—C23—C24 | 109.54 (8) |
C4—C3—C2 | 119.71 (10) | N1—C23—H23A | 109.2 (9) |
C3—O3—H3 | 109.5 | C24—C23—H23A | 105.6 (9) |
C4—C3A—C2 | 119.71 (10) | N1—C23—H23B | 111.9 (9) |
C4—C3A—H3A | 120.1 | C24—C23—H23B | 109.7 (9) |
C2—C3A—H3A | 120.1 | H23A—C23—H23B | 110.7 (13) |
C31—C8—C9 | 120.26 (9) | N2—C24—C23 | 111.45 (8) |
C31—C8—H8 | 119.0 (10) | N2—C24—H24A | 106.5 (9) |
C9—C8—H8 | 120.6 (10) | C23—C24—H24A | 111.2 (9) |
C10—C9—C8 | 120.30 (9) | N2—C24—H24B | 106.6 (9) |
C10—C9—H9 | 121.4 (9) | C23—C24—H24B | 111.9 (9) |
C8—C9—H9 | 118.3 (9) | H24A—C24—H24B | 108.9 (13) |
O5—C10—C9 | 124.10 (9) | C26—C25—C19 | 119.83 (10) |
O5—C10—C11 | 115.80 (8) | C26—C25—H25 | 122.5 (10) |
C9—C10—C11 | 120.07 (9) | C19—C25—H25 | 117.7 (9) |
C30—C11—C10 | 118.30 (9) | C25—C26—C27 | 121.51 (10) |
C30—C11—N1 | 122.69 (9) | C25—C26—H26 | 120.6 (10) |
C10—C11—N1 | 118.90 (8) | C27—C26—H26 | 117.9 (10) |
N1—C12—C13 | 109.86 (8) | C17—C27—C26 | 119.33 (11) |
N1—C12—H12A | 111.6 (9) | C17—C27—H27 | 119.1 (10) |
C13—C12—H12A | 109.3 (9) | C26—C27—H27 | 121.5 (10) |
N1—C12—H12B | 107.9 (10) | C29—C28—C21 | 120.06 (10) |
C13—C12—H12B | 108.1 (9) | C29—C28—H28 | 121.5 (10) |
H12A—C12—H12B | 110.1 (13) | C21—C28—H28 | 118.4 (10) |
N2—C13—C12 | 111.74 (8) | C28—C29—C18 | 120.43 (9) |
N2—C13—H13A | 109.1 (10) | C28—C29—H29 | 120.6 (9) |
C12—C13—H13A | 110.2 (10) | C18—C29—H29 | 118.8 (9) |
N2—C13—H13B | 108.3 (9) | C11—C30—C31 | 121.64 (9) |
C12—C13—H13B | 109.1 (9) | C11—C30—H30 | 116.9 (10) |
H13A—C13—H13B | 108.3 (14) | C31—C30—H30 | 121.5 (10) |
N2—C14—C15 | 113.79 (8) | C8—C31—C30 | 119.42 (10) |
N2—C14—H14A | 106.7 (9) | C8—C31—H31 | 120.0 (9) |
C15—C14—H14A | 111.1 (9) | C30—C31—H31 | 120.6 (9) |
N2—C14—H14B | 105.8 (9) | ||
O1—C1—C2—C7 | −3.35 (14) | C13—N2—C14—C15 | 57.95 (10) |
O2—C1—C2—C7 | 175.48 (9) | C24—N2—C14—C15 | −179.23 (8) |
O1—C1—C2—C3A | 178.87 (9) | N2—C14—C15—O6 | 50.28 (11) |
O2—C1—C2—C3A | −2.30 (14) | N2—C14—C15—C16 | 174.96 (8) |
O1—C1—C2—C3 | 178.87 (9) | C17—O4—C16—C15 | 167.01 (9) |
O2—C1—C2—C3 | −2.30 (14) | O6—C15—C16—O4 | 57.56 (11) |
C3A—C4—C5—C6 | −0.18 (16) | C14—C15—C16—O4 | −66.61 (10) |
C3—C4—C5—C6 | −0.18 (16) | C16—O4—C17—C27 | 9.19 (15) |
C4—C5—C6—C7 | −0.25 (16) | C16—O4—C17—C18 | −172.24 (9) |
C5—C6—C7—C2 | 0.36 (16) | O4—C17—C18—C29 | −6.77 (14) |
C3A—C2—C7—C6 | −0.04 (15) | C27—C17—C18—C29 | 171.86 (10) |
C3—C2—C7—C6 | −0.04 (15) | O4—C17—C18—C19 | 175.70 (8) |
C1—C2—C7—C6 | −177.86 (9) | C27—C17—C18—C19 | −5.68 (15) |
C5—C4—C3—O3 | −178.91 (10) | C29—C18—C19—C20 | −0.25 (14) |
C5—C4—C3—C2 | 0.50 (16) | C17—C18—C19—C20 | 177.34 (9) |
C7—C2—C3—O3 | 178.99 (10) | C29—C18—C19—C25 | −176.27 (9) |
C1—C2—C3—O3 | −3.18 (15) | C17—C18—C19—C25 | 1.32 (14) |
C7—C2—C3—C4 | −0.39 (14) | C18—C19—C20—C21 | −1.95 (15) |
C1—C2—C3—C4 | 177.43 (9) | C25—C19—C20—C21 | 173.96 (10) |
C5—C4—C3A—C2 | 0.50 (16) | C19—C20—C21—C28 | 2.22 (16) |
C7—C2—C3A—C4 | −0.39 (14) | C11—N1—C23—C24 | 165.02 (8) |
C1—C2—C3A—C4 | 177.43 (9) | C12—N1—C23—C24 | −64.28 (10) |
C31—C8—C9—C10 | −0.20 (16) | C14—N2—C24—C23 | −174.04 (7) |
C22—O5—C10—C9 | 0.79 (14) | C13—N2—C24—C23 | −50.75 (10) |
C22—O5—C10—C11 | 179.04 (9) | N1—C23—C24—N2 | 58.32 (10) |
C8—C9—C10—O5 | 177.41 (9) | C20—C19—C25—C26 | −172.13 (10) |
C8—C9—C10—C11 | −0.77 (15) | C18—C19—C25—C26 | 3.75 (15) |
O5—C10—C11—C30 | −177.32 (9) | C19—C25—C26—C27 | −4.68 (17) |
C9—C10—C11—C30 | 1.00 (14) | O4—C17—C27—C26 | −176.64 (10) |
O5—C10—C11—N1 | −0.96 (13) | C18—C17—C27—C26 | 4.89 (16) |
C9—C10—C11—N1 | 177.37 (9) | C25—C26—C27—C17 | 0.36 (17) |
C23—N1—C11—C30 | 12.19 (13) | C20—C21—C28—C29 | −0.22 (16) |
C12—N1—C11—C30 | −115.36 (10) | C21—C28—C29—C18 | −2.00 (16) |
C23—N1—C11—C10 | −164.01 (8) | C19—C18—C29—C28 | 2.22 (15) |
C12—N1—C11—C10 | 68.45 (11) | C17—C18—C29—C28 | −175.29 (9) |
C11—N1—C12—C13 | −165.35 (8) | C10—C11—C30—C31 | −0.29 (15) |
C23—N1—C12—C13 | 63.56 (10) | N1—C11—C30—C31 | −176.51 (9) |
C14—N2—C13—C12 | 171.27 (8) | C9—C8—C31—C30 | 0.91 (16) |
C24—N2—C13—C12 | 50.06 (10) | C11—C30—C31—C8 | −0.67 (16) |
N1—C12—C13—N2 | −56.76 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2 | 0.968 (18) | 2.581 (18) | 3.2396 (13) | 125.4 (13) |
C14—H14B···O2 | 0.968 (16) | 2.603 (16) | 3.1698 (14) | 117.6 (11) |
C31H34.42N2O6.42 | F(000) = 1143 |
Mr = 537.74 | Dx = 1.325 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.282 (4) Å | Cell parameters from 9534 reflections |
b = 17.856 (7) Å | θ = 2.8–27.7° |
c = 13.460 (5) Å | µ = 0.09 mm−1 |
β = 96.060 (12)° | T = 100 K |
V = 2696.3 (17) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.1 × 0.1 mm |
Bruker APEX-II CCD diffractometer | 5411 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.056 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0822 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.9437. The λ/2 correction factor is Not present. | θmax = 28.2°, θmin = 2.5° |
Tmin = 0.704, Tmax = 0.746 | h = −15→15 |
88550 measured reflections | k = −23→23 |
6635 independent reflections | l = −17→17 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.069 | H-atom parameters constrained |
wR(F2) = 0.227 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.62 | (Δ/σ)max < 0.001 |
6635 reflections | Δρmax = 0.32 e Å−3 |
365 parameters | Δρmin = −0.32 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C3A | 0.5454 (2) | 0.04867 (12) | 1.39865 (15) | 0.0445 (5) | 0.71 |
C4A | 0.5212 (2) | −0.01970 (12) | 1.34849 (16) | 0.0504 (6) | 0.71 |
O3 | 0.6550 (2) | 0.06218 (15) | 1.4321 (2) | 0.0604 (6) | 0.71 |
H3 | 0.659064 | 0.103281 | 1.462584 | 0.091* | 0.71 |
O4 | 0.6093 (2) | −0.06842 (15) | 1.34212 (19) | 0.0680 (7) | 0.71 |
H4 | 0.665932 | −0.058329 | 1.385661 | 0.102* | 0.71 |
C3B | 0.5454 (2) | 0.04867 (12) | 1.39865 (15) | 0.0445 (5) | 0.29 |
H3B | 0.624577 | 0.060583 | 1.425166 | 0.053* | 0.29 |
C4B | 0.5212 (2) | −0.01970 (12) | 1.34849 (16) | 0.0504 (6) | 0.29 |
H4B | 0.584220 | −0.054070 | 1.341975 | 0.060* | 0.29 |
N1 | 0.31020 (14) | 0.05642 (9) | 0.96114 (11) | 0.0357 (4) | |
N2 | 0.49089 (14) | 0.15530 (8) | 1.05485 (11) | 0.0345 (4) | |
H2 | 0.458886 | 0.206879 | 1.040817 | 0.041* | |
O5 | 0.20401 (14) | −0.05813 (9) | 1.04849 (11) | 0.0509 (4) | |
O1 | 0.39569 (15) | 0.21497 (9) | 1.47493 (14) | 0.0588 (5) | |
O6 | 0.54994 (17) | 0.26796 (9) | 1.20614 (13) | 0.0580 (4) | |
H6 | 0.572653 | 0.294272 | 1.160004 | 0.087* | |
O7 | 0.79671 (14) | 0.26140 (9) | 1.19735 (12) | 0.0549 (4) | |
C19 | 0.61210 (18) | 0.16218 (11) | 1.11069 (16) | 0.0410 (4) | |
H19A | 0.663626 | 0.191038 | 1.069427 | 0.049* | |
H19B | 0.646900 | 0.111482 | 1.120520 | 0.049* | |
C14 | 0.20640 (17) | 0.02215 (10) | 0.90953 (15) | 0.0368 (4) | |
C22 | 0.91866 (19) | 0.26624 (11) | 1.20532 (17) | 0.0453 (5) | |
O2 | 0.58376 (17) | 0.18028 (11) | 1.50646 (17) | 0.0742 (6) | |
C9 | 0.15221 (18) | −0.03775 (11) | 0.95560 (15) | 0.0398 (4) | |
C2 | 0.45374 (19) | 0.09840 (10) | 1.40922 (14) | 0.0400 (4) | |
C20 | 0.6134 (2) | 0.20024 (12) | 1.21246 (16) | 0.0457 (5) | |
H20 | 0.572616 | 0.165929 | 1.256729 | 0.055* | |
C15 | 0.28888 (18) | 0.09837 (12) | 1.05107 (15) | 0.0417 (5) | |
H15A | 0.236088 | 0.069077 | 1.090707 | 0.050* | |
H15B | 0.248534 | 0.146237 | 1.031779 | 0.050* | |
C31 | 0.96374 (18) | 0.30948 (11) | 1.12957 (16) | 0.0416 (5) | |
C1 | 0.4789 (2) | 0.16973 (12) | 1.46721 (17) | 0.0473 (5) | |
C30 | 0.88895 (19) | 0.35083 (13) | 1.05809 (16) | 0.0473 (5) | |
H30 | 0.804895 | 0.347929 | 1.058292 | 0.057* | |
C7 | 0.3386 (2) | 0.07944 (12) | 1.36770 (17) | 0.0488 (5) | |
H7 | 0.274711 | 0.113239 | 1.373692 | 0.059* | |
C16 | 0.40539 (18) | 0.11399 (11) | 1.11348 (14) | 0.0405 (4) | |
H16A | 0.389981 | 0.144175 | 1.172456 | 0.049* | |
H16B | 0.441810 | 0.066038 | 1.137735 | 0.049* | |
C18 | 0.38136 (19) | 0.10248 (12) | 0.90054 (15) | 0.0434 (5) | |
H18A | 0.340011 | 0.150537 | 0.884362 | 0.052* | |
H18B | 0.391426 | 0.076387 | 0.837073 | 0.052* | |
C8 | 0.1510 (3) | −0.11842 (15) | 1.0972 (2) | 0.0655 (7) | |
H8A | 0.151196 | −0.163568 | 1.055866 | 0.098* | |
H8B | 0.068682 | −0.105350 | 1.107231 | 0.098* | |
H8C | 0.196495 | −0.127793 | 1.162142 | 0.098* | |
C21 | 0.7421 (2) | 0.20961 (13) | 1.25892 (18) | 0.0539 (6) | |
H21A | 0.744127 | 0.229104 | 1.327934 | 0.065* | |
H21B | 0.784365 | 0.160952 | 1.260938 | 0.065* | |
C26 | 1.09021 (19) | 0.31341 (12) | 1.12655 (18) | 0.0470 (5) | |
C10 | 0.0540 (2) | −0.07389 (12) | 0.90564 (19) | 0.0506 (5) | |
H10 | 0.017183 | −0.114182 | 0.936766 | 0.061* | |
C29 | 0.9358 (2) | 0.39467 (15) | 0.98910 (17) | 0.0537 (6) | |
H29 | 0.884298 | 0.422903 | 0.942892 | 0.064* | |
C27 | 1.1345 (2) | 0.35806 (15) | 1.05140 (19) | 0.0571 (6) | |
H27 | 1.217855 | 0.359805 | 1.046777 | 0.069* | |
C25 | 1.1662 (2) | 0.27606 (14) | 1.2023 (2) | 0.0613 (7) | |
H25 | 1.250119 | 0.276666 | 1.200347 | 0.074* | |
C12 | 0.0625 (2) | 0.00694 (14) | 0.76406 (19) | 0.0562 (6) | |
H12 | 0.032741 | 0.022036 | 0.698443 | 0.067* | |
C11 | 0.0098 (2) | −0.05084 (14) | 0.8097 (2) | 0.0565 (6) | |
H11 | −0.057437 | −0.075451 | 0.775893 | 0.068* | |
C28 | 1.0597 (2) | 0.39842 (16) | 0.98583 (18) | 0.0581 (6) | |
H28 | 1.091434 | 0.429282 | 0.937608 | 0.070* | |
C6 | 0.3167 (2) | 0.01254 (13) | 1.31832 (19) | 0.0566 (6) | |
H6A | 0.238093 | 0.000486 | 1.290430 | 0.068* | |
C23 | 0.9938 (2) | 0.23408 (12) | 1.2794 (2) | 0.0582 (6) | |
H23 | 0.962612 | 0.208016 | 1.332436 | 0.070* | |
C5 | 0.4087 (2) | −0.03696 (12) | 1.30934 (17) | 0.0544 (6) | |
H5A | 0.393355 | −0.083270 | 1.275677 | 0.065* | 0.71 |
H5B | 0.393355 | −0.083270 | 1.275677 | 0.065* | 0.71 |
C13 | 0.1595 (2) | 0.04324 (12) | 0.81431 (16) | 0.0477 (5) | |
H13 | 0.194984 | 0.083769 | 0.782561 | 0.057* | |
C24 | 1.1187 (3) | 0.23984 (13) | 1.2768 (2) | 0.0673 (8) | |
H24 | 1.170394 | 0.217607 | 1.328797 | 0.081* | |
C17 | 0.50166 (19) | 0.11725 (11) | 0.95688 (15) | 0.0405 (4) | |
H17A | 0.544532 | 0.069204 | 0.969081 | 0.049* | |
H17B | 0.549062 | 0.149150 | 0.915712 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C3A | 0.0516 (12) | 0.0448 (11) | 0.0379 (10) | 0.0042 (9) | 0.0084 (9) | −0.0019 (8) |
C4A | 0.0729 (16) | 0.0422 (11) | 0.0373 (10) | 0.0180 (10) | 0.0115 (10) | −0.0003 (8) |
O3 | 0.0435 (12) | 0.0692 (16) | 0.0669 (15) | 0.0081 (11) | −0.0017 (11) | −0.0225 (12) |
O4 | 0.0734 (17) | 0.0665 (16) | 0.0609 (15) | 0.0345 (13) | −0.0070 (12) | −0.0186 (12) |
C3B | 0.0516 (12) | 0.0448 (11) | 0.0379 (10) | 0.0042 (9) | 0.0084 (9) | −0.0019 (8) |
C4B | 0.0729 (16) | 0.0422 (11) | 0.0373 (10) | 0.0180 (10) | 0.0115 (10) | −0.0003 (8) |
N1 | 0.0382 (8) | 0.0336 (8) | 0.0354 (8) | −0.0064 (6) | 0.0051 (6) | 0.0006 (6) |
N2 | 0.0402 (9) | 0.0248 (7) | 0.0392 (8) | −0.0038 (6) | 0.0072 (6) | 0.0002 (6) |
O5 | 0.0535 (9) | 0.0438 (8) | 0.0548 (9) | −0.0110 (7) | 0.0021 (7) | 0.0136 (7) |
O1 | 0.0605 (10) | 0.0354 (8) | 0.0820 (12) | 0.0020 (7) | 0.0146 (9) | −0.0134 (8) |
O6 | 0.0717 (11) | 0.0455 (9) | 0.0572 (10) | 0.0008 (8) | 0.0092 (8) | −0.0066 (7) |
O7 | 0.0475 (9) | 0.0538 (9) | 0.0609 (10) | −0.0122 (7) | −0.0064 (7) | 0.0178 (7) |
C19 | 0.0394 (10) | 0.0349 (9) | 0.0484 (11) | −0.0030 (8) | 0.0039 (8) | −0.0006 (8) |
C14 | 0.0366 (10) | 0.0297 (9) | 0.0439 (10) | −0.0009 (7) | 0.0038 (8) | −0.0015 (7) |
C22 | 0.0467 (12) | 0.0331 (9) | 0.0533 (12) | −0.0054 (8) | −0.0077 (9) | −0.0035 (8) |
O2 | 0.0577 (11) | 0.0619 (11) | 0.1003 (15) | 0.0008 (9) | −0.0037 (10) | −0.0345 (10) |
C9 | 0.0399 (10) | 0.0339 (9) | 0.0454 (10) | 0.0007 (8) | 0.0037 (8) | 0.0009 (8) |
C2 | 0.0542 (12) | 0.0312 (9) | 0.0363 (9) | 0.0005 (8) | 0.0124 (8) | −0.0008 (7) |
C20 | 0.0554 (13) | 0.0390 (10) | 0.0423 (11) | −0.0094 (9) | 0.0034 (9) | 0.0041 (8) |
C15 | 0.0429 (11) | 0.0408 (10) | 0.0430 (10) | −0.0078 (8) | 0.0127 (8) | −0.0058 (8) |
C31 | 0.0417 (11) | 0.0337 (9) | 0.0476 (11) | −0.0023 (8) | −0.0032 (8) | −0.0085 (8) |
C1 | 0.0568 (13) | 0.0356 (10) | 0.0515 (12) | −0.0036 (9) | 0.0158 (10) | −0.0049 (8) |
C30 | 0.0388 (11) | 0.0535 (12) | 0.0484 (11) | −0.0044 (9) | −0.0015 (9) | −0.0003 (9) |
C7 | 0.0582 (13) | 0.0410 (11) | 0.0481 (11) | −0.0002 (9) | 0.0098 (10) | −0.0004 (9) |
C16 | 0.0484 (11) | 0.0389 (10) | 0.0358 (9) | −0.0110 (8) | 0.0122 (8) | −0.0005 (8) |
C18 | 0.0496 (12) | 0.0444 (11) | 0.0373 (10) | −0.0092 (9) | 0.0094 (8) | 0.0011 (8) |
C8 | 0.0795 (18) | 0.0524 (14) | 0.0663 (15) | −0.0138 (12) | 0.0152 (13) | 0.0192 (12) |
C21 | 0.0649 (15) | 0.0463 (12) | 0.0481 (12) | −0.0136 (10) | −0.0050 (10) | 0.0104 (9) |
C26 | 0.0410 (11) | 0.0400 (10) | 0.0582 (13) | 0.0011 (8) | −0.0022 (9) | −0.0173 (9) |
C10 | 0.0449 (12) | 0.0377 (11) | 0.0688 (14) | −0.0083 (9) | 0.0037 (10) | −0.0034 (10) |
C29 | 0.0464 (12) | 0.0667 (15) | 0.0474 (12) | −0.0017 (10) | 0.0027 (9) | 0.0040 (10) |
C27 | 0.0425 (12) | 0.0656 (15) | 0.0643 (15) | −0.0039 (10) | 0.0104 (11) | −0.0154 (12) |
C25 | 0.0464 (13) | 0.0442 (13) | 0.0889 (19) | 0.0078 (10) | −0.0130 (12) | −0.0103 (12) |
C12 | 0.0586 (14) | 0.0561 (13) | 0.0505 (13) | −0.0016 (11) | −0.0099 (11) | −0.0028 (10) |
C11 | 0.0490 (13) | 0.0501 (13) | 0.0668 (15) | −0.0037 (10) | −0.0104 (11) | −0.0131 (11) |
C28 | 0.0518 (13) | 0.0733 (16) | 0.0504 (13) | −0.0082 (12) | 0.0111 (10) | −0.0030 (11) |
C6 | 0.0645 (15) | 0.0481 (13) | 0.0564 (14) | −0.0071 (11) | 0.0022 (11) | −0.0045 (10) |
C23 | 0.0633 (15) | 0.0387 (11) | 0.0682 (15) | −0.0042 (10) | −0.0141 (12) | 0.0104 (10) |
C5 | 0.0833 (18) | 0.0354 (10) | 0.0428 (11) | −0.0008 (10) | −0.0010 (11) | −0.0034 (8) |
C13 | 0.0542 (13) | 0.0415 (11) | 0.0460 (11) | −0.0028 (9) | −0.0012 (9) | 0.0037 (9) |
C24 | 0.0646 (16) | 0.0408 (12) | 0.089 (2) | 0.0063 (11) | −0.0272 (14) | 0.0028 (12) |
C17 | 0.0464 (11) | 0.0369 (10) | 0.0407 (10) | −0.0057 (8) | 0.0157 (8) | −0.0045 (7) |
C3A—O3 | 1.293 (3) | C22—C23 | 1.366 (3) |
C3A—C2 | 1.382 (3) | C22—C31 | 1.415 (3) |
C3A—C4A | 1.408 (3) | O2—C1 | 1.258 (3) |
C4A—O4 | 1.330 (3) | C9—C10 | 1.392 (3) |
C4A—C5 | 1.358 (4) | C2—C7 | 1.400 (3) |
C3B—C2 | 1.382 (3) | C2—C1 | 1.505 (3) |
C3B—C4B | 1.408 (3) | C20—C21 | 1.528 (3) |
C4B—C5 | 1.358 (4) | C15—C16 | 1.509 (3) |
N1—C14 | 1.434 (2) | C31—C30 | 1.418 (3) |
N1—C18 | 1.457 (2) | C31—C26 | 1.433 (3) |
N1—C15 | 1.465 (2) | C30—C29 | 1.363 (3) |
N2—C19 | 1.494 (2) | C7—C6 | 1.377 (3) |
N2—C17 | 1.500 (2) | C18—C17 | 1.506 (3) |
N2—C16 | 1.503 (2) | C26—C27 | 1.419 (4) |
O5—C9 | 1.372 (3) | C26—C25 | 1.426 (3) |
O5—C8 | 1.425 (3) | C10—C11 | 1.396 (4) |
O1—C1 | 1.251 (3) | C29—C28 | 1.404 (3) |
O6—C20 | 1.403 (3) | C27—C28 | 1.361 (4) |
O7—C22 | 1.371 (3) | C25—C24 | 1.351 (4) |
O7—C21 | 1.425 (3) | C12—C11 | 1.368 (4) |
C19—C20 | 1.528 (3) | C12—C13 | 1.386 (3) |
C14—C13 | 1.386 (3) | C6—C5 | 1.379 (4) |
C14—C9 | 1.408 (3) | C23—C24 | 1.416 (4) |
O3—C3A—C2 | 122.9 (2) | O6—C20—C19 | 111.87 (17) |
O3—C3A—C4A | 117.3 (2) | C21—C20—C19 | 109.53 (19) |
C2—C3A—C4A | 119.8 (2) | N1—C15—C16 | 110.19 (16) |
O4—C4A—C5 | 120.0 (2) | C22—C31—C30 | 122.6 (2) |
O4—C4A—C3A | 119.3 (3) | C22—C31—C26 | 118.79 (19) |
C5—C4A—C3A | 120.6 (2) | C30—C31—C26 | 118.6 (2) |
C2—C3B—C4B | 119.8 (2) | O1—C1—O2 | 123.3 (2) |
C5—C4B—C3B | 120.6 (2) | O1—C1—C2 | 119.2 (2) |
C14—N1—C18 | 116.08 (16) | O2—C1—C2 | 117.49 (19) |
C14—N1—C15 | 114.93 (16) | C29—C30—C31 | 121.0 (2) |
C18—N1—C15 | 108.79 (15) | C6—C7—C2 | 121.0 (2) |
C19—N2—C17 | 108.95 (15) | N2—C16—C15 | 111.59 (16) |
C19—N2—C16 | 112.35 (15) | N1—C18—C17 | 109.71 (16) |
C17—N2—C16 | 110.82 (14) | O7—C21—C20 | 106.47 (17) |
C9—O5—C8 | 117.43 (18) | C27—C26—C25 | 122.8 (2) |
C22—O7—C21 | 119.17 (17) | C27—C26—C31 | 118.3 (2) |
N2—C19—C20 | 114.15 (17) | C25—C26—C31 | 118.8 (2) |
C13—C14—C9 | 118.20 (18) | C9—C10—C11 | 119.9 (2) |
C13—C14—N1 | 122.98 (18) | C30—C29—C28 | 120.5 (2) |
C9—C14—N1 | 118.76 (17) | C28—C27—C26 | 121.3 (2) |
C23—C22—O7 | 124.8 (2) | C24—C25—C26 | 119.9 (2) |
C23—C22—C31 | 120.9 (2) | C11—C12—C13 | 119.5 (2) |
O7—C22—C31 | 114.32 (18) | C12—C11—C10 | 120.5 (2) |
O5—C9—C10 | 123.90 (19) | C27—C28—C29 | 120.3 (2) |
O5—C9—C14 | 116.09 (17) | C5—C6—C7 | 120.0 (2) |
C10—C9—C14 | 119.98 (19) | C22—C23—C24 | 119.6 (3) |
C3B—C2—C7 | 118.45 (19) | C4B—C5—C6 | 120.2 (2) |
C3A—C2—C7 | 118.45 (19) | C4A—C5—C6 | 120.2 (2) |
C3B—C2—C1 | 119.7 (2) | C14—C13—C12 | 121.9 (2) |
C3A—C2—C1 | 119.7 (2) | C25—C24—C23 | 121.8 (2) |
C7—C2—C1 | 121.84 (19) | N2—C17—C18 | 111.70 (16) |
O6—C20—C21 | 112.78 (18) |
C62H67.84N4O11.72 | F(000) = 1123 |
Mr = 1056.56 | Dx = 1.332 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.346 (2) Å | Cell parameters from 9941 reflections |
b = 17.508 (4) Å | θ = 2.5–29.0° |
c = 13.400 (3) Å | µ = 0.09 mm−1 |
β = 98.15 (3)° | T = 100 K |
V = 2635.0 (10) Å3 | Block, colourless |
Z = 2 | 0.19 × 0.15 × 0.09 mm |
Bruker APEX-II CCD diffractometer | 10798 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.071 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0948 before and 0.0623 after correction. The Ratio of minimum to maximum transmission is 0.9102. The λ/2 correction factor is Not present. | θmax = 30.5°, θmin = 2.2° |
Tmin = 0.679, Tmax = 0.746 | h = −16→16 |
65036 measured reflections | k = −24→24 |
15959 independent reflections | l = −19→19 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.083 | w = 1/[σ2(Fo2) + (0.0303P)2 + 3.0563P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.163 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.29 e Å−3 |
15959 reflections | Δρmin = −0.25 e Å−3 |
730 parameters | Absolute structure: Refined as an inversion twin. |
1 restraint | Absolute structure parameter: −0.2 (17) |
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) | |
C1A | 0.5715 (5) | 0.2152 (3) | −0.3430 (4) | 0.0329 (11) | 0.2 |
C2A | 0.3651 (5) | 0.1785 (3) | −0.3797 (4) | 0.0324 (11) | 0.2 |
C3A | −0.3758 (5) | 0.3215 (3) | −0.1178 (4) | 0.0321 (11) | 0.66 |
C4A | −0.5859 (4) | 0.3033 (3) | −0.1461 (4) | 0.0296 (10) | 0.66 |
O3 | 0.6939 (19) | 0.2164 (14) | −0.3066 (18) | 0.062 (7) | 0.2 |
H3 | 0.703602 | 0.214410 | −0.244889 | 0.094* | 0.2 |
O4 | 0.300 (2) | 0.126 (2) | −0.381 (3) | 0.112 (14) | 0.2 |
H4 | 0.320435 | 0.098481 | −0.332051 | 0.169* | 0.2 |
O5 | −0.2811 (5) | 0.3578 (4) | −0.1301 (6) | 0.0533 (17) | 0.66 |
H5 | −0.230478 | 0.327519 | −0.143440 | 0.080* | 0.66 |
O6 | −0.7031 (6) | 0.3252 (4) | −0.1782 (5) | 0.0537 (17) | 0.66 |
H6 | −0.703656 | 0.364545 | −0.211458 | 0.081* | 0.66 |
C1B | 0.5715 (5) | 0.2152 (3) | −0.3430 (4) | 0.0329 (11) | 0.8 |
H1B | 0.649001 | 0.204978 | −0.313315 | 0.039* | 0.72 |
C2B | 0.3651 (5) | 0.1785 (3) | −0.3797 (4) | 0.0324 (11) | 0.8 |
H2B | 0.304416 | 0.143641 | −0.374504 | 0.039* | 0.72 |
C3B | −0.3758 (5) | 0.3215 (3) | −0.1178 (4) | 0.0321 (11) | 0.34 |
H3B | −0.308868 | 0.350065 | −0.126392 | 0.039* | 0.34 |
C4B | −0.5859 (4) | 0.3033 (3) | −0.1461 (4) | 0.0296 (10) | 0.34 |
H4B | −0.661613 | 0.318910 | −0.174652 | 0.035* | 0.34 |
O11 | 0.1652 (3) | 0.5155 (2) | 0.0700 (3) | 0.0402 (9) | |
O10 | 0.4039 (4) | 0.5218 (2) | 0.0437 (3) | 0.0389 (9) | |
H10 | 0.394716 | 0.546169 | 0.094306 | 0.058* | |
O005 | 0.7728 (3) | 0.19269 (19) | 0.1990 (2) | 0.0341 (8) | |
N00A | 0.4842 (4) | 0.4105 (2) | 0.1971 (3) | 0.0245 (8) | |
H00A | 0.515786 | 0.462374 | 0.207911 | 0.029* | |
N00B | 0.6736 (4) | 0.3102 (2) | 0.2867 (3) | 0.0261 (8) | |
C00F | 0.7821 (4) | 0.2778 (3) | 0.3363 (3) | 0.0259 (9) | |
C00K | 0.8354 (5) | 0.3014 (3) | 0.4305 (4) | 0.0323 (11) | |
H00K | 0.802756 | 0.342137 | 0.461749 | 0.039* | |
C00L | 0.8325 (4) | 0.2156 (3) | 0.2902 (4) | 0.0298 (10) | |
C00R | 0.5613 (5) | 0.3673 (3) | 0.1350 (3) | 0.0300 (10) | |
H00B | 0.569294 | 0.396292 | 0.074617 | 0.036* | |
H00C | 0.523894 | 0.318933 | 0.114515 | 0.036* | |
C00T | 0.0450 (5) | 0.5229 (3) | 0.0674 (4) | 0.0404 (13) | |
C00V | 0.3419 (5) | 0.4515 (3) | 0.0433 (4) | 0.0342 (11) | |
H00V | 0.375274 | 0.416731 | −0.002680 | 0.041* | |
C00W | 0.6846 (5) | 0.3527 (3) | 0.1940 (4) | 0.0307 (11) | |
H00D | 0.732240 | 0.323684 | 0.152780 | 0.037* | |
H00E | 0.724360 | 0.401035 | 0.210915 | 0.037* | |
C00X | 0.9875 (5) | 0.2058 (3) | 0.4333 (4) | 0.0379 (12) | |
H00X | 1.056634 | 0.182652 | 0.464860 | 0.045* | |
C00Y | 0.4845 (4) | 0.3729 (3) | 0.2976 (4) | 0.0286 (10) | |
H00F | 0.442287 | 0.324684 | 0.288327 | 0.034* | |
H00G | 0.442471 | 0.405185 | 0.339710 | 0.034* | |
C016 | −0.1129 (6) | 0.5835 (4) | 0.1441 (5) | 0.0517 (16) | |
C019 | 0.6090 (4) | 0.3587 (3) | 0.3503 (3) | 0.0289 (10) | |
H01A | 0.650416 | 0.406920 | 0.363325 | 0.035* | |
H01B | 0.605698 | 0.333659 | 0.414438 | 0.035* | |
C01A | 0.2100 (5) | 0.4601 (3) | 0.0062 (4) | 0.0399 (13) | |
H01C | 0.197551 | 0.477294 | −0.063362 | 0.048* | |
H01D | 0.169507 | 0.411630 | 0.010144 | 0.048* | |
C01B | 0.9372 (5) | 0.2654 (3) | 0.4796 (4) | 0.0360 (12) | |
H01E | 0.970936 | 0.281579 | 0.543356 | 0.043* | |
C01D | 0.0945 (6) | 0.6183 (3) | 0.2021 (4) | 0.0416 (13) | |
H01F | 0.175510 | 0.611707 | 0.200131 | 0.050* | |
C01F | 0.0559 (6) | 0.6710 (4) | 0.2668 (4) | 0.0574 (18) | |
H01G | 0.110909 | 0.700853 | 0.307578 | 0.069* | |
C01H | 0.3580 (5) | 0.4153 (3) | 0.1463 (4) | 0.0306 (11) | |
H01H | 0.312242 | 0.444189 | 0.189209 | 0.037* | |
H01I | 0.325145 | 0.364051 | 0.140228 | 0.037* | |
C01I | 0.0104 (5) | 0.5745 (3) | 0.1391 (4) | 0.0390 (13) | |
C01M | 0.9341 (5) | 0.1805 (3) | 0.3387 (4) | 0.0356 (12) | |
H01M | 0.967201 | 0.139609 | 0.308008 | 0.043* | |
C01O | 0.8178 (6) | 0.1272 (3) | 0.1516 (4) | 0.0444 (14) | |
H01J | 0.767666 | 0.116764 | 0.089121 | 0.067* | |
H01K | 0.818271 | 0.083733 | 0.195321 | 0.067* | |
H01L | 0.897345 | 0.137352 | 0.138585 | 0.067* | |
C01R | −0.0402 (6) | 0.4855 (3) | 0.0015 (6) | 0.0582 (19) | |
H01R | −0.017675 | 0.454690 | −0.049095 | 0.070* | |
C01S | −0.1480 (7) | 0.6368 (5) | 0.2128 (4) | 0.068 (2) | |
H01S | −0.228307 | 0.642552 | 0.218179 | 0.082* | |
C01T | −0.1985 (6) | 0.5416 (4) | 0.0793 (6) | 0.062 (2) | |
H01T | −0.279218 | 0.546689 | 0.083635 | 0.075* | |
C01W | −0.1610 (6) | 0.4940 (3) | 0.0112 (7) | 0.070 (2) | |
H01W | −0.217230 | 0.465889 | −0.030857 | 0.084* | |
C01Y | −0.0661 (7) | 0.6797 (5) | 0.2713 (5) | 0.071 (2) | |
H01Y | −0.091193 | 0.715509 | 0.315051 | 0.085* | |
O002 | −0.8059 (3) | 0.30918 (19) | 0.3051 (3) | 0.0344 (8) | |
O007 | −0.4368 (4) | −0.0150 (2) | 0.4591 (3) | 0.0447 (10) | |
H007 | −0.424996 | −0.034676 | 0.405836 | 0.067* | |
N00C | −0.5127 (4) | 0.0985 (2) | 0.3099 (3) | 0.0274 (9) | |
H00H | −0.538720 | 0.045517 | 0.297563 | 0.033* | |
N00D | −0.7046 (3) | 0.1941 (2) | 0.2159 (3) | 0.0264 (8) | |
O9 | −0.1927 (4) | 0.0040 (2) | 0.4523 (3) | 0.0514 (11) | |
C00G | −0.9674 (5) | 0.3223 (3) | 0.1649 (4) | 0.0350 (12) | |
H00I | −1.002291 | 0.361746 | 0.196807 | 0.042* | |
C00I | −0.6354 (4) | 0.1487 (3) | 0.1542 (4) | 0.0292 (10) | |
H00J | −0.631821 | 0.174500 | 0.090612 | 0.035* | |
H00L | −0.673361 | 0.099475 | 0.139782 | 0.035* | |
C00M | −0.8646 (4) | 0.2877 (3) | 0.2128 (4) | 0.0290 (10) | |
C00S | −0.5110 (4) | 0.1373 (3) | 0.2091 (3) | 0.0276 (10) | |
H00M | −0.471791 | 0.186425 | 0.219735 | 0.033* | |
H00N | −0.465606 | 0.106369 | 0.168058 | 0.033* | |
C010 | −0.7174 (5) | 0.1507 (3) | 0.3082 (4) | 0.0353 (12) | |
H01N | −0.755400 | 0.102069 | 0.290128 | 0.042* | |
H01O | −0.767478 | 0.178971 | 0.348177 | 0.042* | |
C012 | −0.5986 (5) | 0.1374 (3) | 0.3688 (4) | 0.0340 (11) | |
H01P | −0.608571 | 0.106321 | 0.426918 | 0.041* | |
H01Q | −0.565297 | 0.186069 | 0.393258 | 0.041* | |
C013 | −0.3897 (5) | 0.0978 (3) | 0.3659 (4) | 0.0355 (12) | |
H01U | −0.362080 | 0.150050 | 0.375896 | 0.043* | |
H01V | −0.337536 | 0.072128 | 0.325178 | 0.043* | |
C015 | −0.8537 (5) | 0.3739 (3) | 0.3522 (4) | 0.0373 (12) | |
H01X | −0.856711 | 0.417190 | 0.307935 | 0.056* | |
H01Z | −0.803800 | 0.385486 | 0.414307 | 0.056* | |
H | −0.932599 | 0.362133 | 0.365656 | 0.056* | |
C01C | −1.0188 (5) | 0.2985 (3) | 0.0694 (5) | 0.0404 (13) | |
H01 | −1.087776 | 0.321918 | 0.037942 | 0.049* | |
C01G | −0.9673 (5) | 0.2403 (3) | 0.0216 (4) | 0.0381 (12) | |
H0AA | −1.000615 | 0.224997 | −0.042745 | 0.046* | |
C01J | −0.8122 (4) | 0.2266 (2) | 0.1656 (4) | 0.0291 (10) | |
C01N | −0.8655 (5) | 0.2045 (3) | 0.0697 (4) | 0.0328 (11) | |
H1AA | −0.832027 | 0.164785 | 0.037151 | 0.039* | |
C01P | −0.0227 (6) | −0.0410 (3) | 0.3886 (5) | 0.0536 (17) | |
C01U | −0.3800 (6) | 0.0577 (3) | 0.4695 (4) | 0.0424 (14) | |
H2AA | −0.421991 | 0.089152 | 0.513674 | 0.051* | |
C01V | −0.2523 (7) | 0.0529 (3) | 0.5155 (5) | 0.0570 (18) | |
H3AA | −0.216479 | 0.103272 | 0.519567 | 0.068* | |
HA | −0.246020 | 0.031887 | 0.583056 | 0.068* | |
C01X | −0.0970 (7) | −0.0777 (4) | 0.3098 (5) | 0.0591 (19) | |
H4AA | −0.179359 | −0.074288 | 0.305899 | 0.071* | |
C01Z | 0.1017 (7) | −0.0446 (4) | 0.3939 (7) | 0.074 (3) | |
C020 | 0.0017 (8) | 0.0286 (3) | 0.5500 (6) | 0.078 (3) | |
H020 | −0.029924 | 0.051383 | 0.602946 | 0.093* | |
C021 | −0.0712 (6) | −0.0002 (3) | 0.4677 (5) | 0.0559 (18) | |
C022 | 0.1492 (8) | −0.0854 (6) | 0.3177 (8) | 0.089 (3) | |
H022 | 0.231255 | −0.086807 | 0.318421 | 0.106* | |
C023 | −0.0479 (7) | −0.1185 (5) | 0.2390 (5) | 0.074 (2) | |
H023 | −0.097530 | −0.143363 | 0.188060 | 0.089* | |
C024 | 0.1758 (9) | −0.0106 (5) | 0.4766 (10) | 0.102 (4) | |
H024 | 0.258063 | −0.011096 | 0.478969 | 0.123* | |
C025 | 0.1264 (9) | 0.0223 (4) | 0.5513 (10) | 0.109 (4) | |
H025 | 0.176349 | 0.041869 | 0.606429 | 0.131* | |
C026 | 0.0758 (9) | −0.1235 (7) | 0.2418 (7) | 0.096 (3) | |
H026 | 0.108260 | −0.151818 | 0.193621 | 0.115* | |
O8 | −0.4121 (3) | 0.4591 (2) | −0.2287 (3) | 0.0383 (9) | |
O7 | −0.6049 (4) | 0.4367 (2) | −0.2649 (3) | 0.0424 (9) | |
C00N | −0.4604 (5) | 0.2105 (3) | −0.0517 (4) | 0.0338 (11) | |
H00O | −0.451390 | 0.164573 | −0.016523 | 0.041* | |
C00O | −0.4880 (4) | 0.3480 (3) | −0.1587 (4) | 0.0276 (10) | |
C00Q | −0.3614 (5) | 0.2532 (3) | −0.0642 (4) | 0.0321 (11) | |
H00Q | −0.285792 | 0.236504 | −0.037162 | 0.039* | 0.66 |
H00P | −0.285792 | 0.236504 | −0.037162 | 0.039* | 0.34 |
C00Z | −0.5027 (5) | 0.4193 (3) | −0.2216 (4) | 0.0309 (11) | |
C018 | −0.5725 (5) | 0.2354 (3) | −0.0912 (4) | 0.0348 (11) | |
H018 | −0.639151 | 0.207028 | −0.081175 | 0.042* | 0.66 |
H8AA | −0.639151 | 0.207028 | −0.081175 | 0.042* | 0.34 |
O1 | 0.4232 (3) | 0.04396 (19) | −0.2678 (3) | 0.0375 (9) | |
O2 | 0.6121 (4) | 0.0820 (2) | −0.2315 (3) | 0.0439 (10) | |
C00P | 0.5076 (5) | 0.0904 (3) | −0.2735 (4) | 0.0324 (11) | |
C00U | 0.4805 (5) | 0.1633 (3) | −0.3341 (3) | 0.0261 (10) | |
C017 | 0.5451 (5) | 0.2827 (3) | −0.3970 (4) | 0.0396 (13) | |
H017 | 0.605224 | 0.317784 | −0.403075 | 0.048* | 0.28 |
H5AA | 0.605224 | 0.317784 | −0.403075 | 0.048* | 0.72 |
C01E | 0.4302 (5) | 0.2977 (3) | −0.4413 (4) | 0.0379 (13) | |
H6AA | 0.413510 | 0.342934 | −0.476908 | 0.045* | |
C01L | 0.3405 (5) | 0.2467 (3) | −0.4335 (4) | 0.0362 (12) | |
H7AA | 0.263318 | 0.257257 | −0.463874 | 0.043* | 0.28 |
HB | 0.263318 | 0.257257 | −0.463874 | 0.043* | 0.72 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.038 (3) | 0.037 (3) | 0.024 (2) | −0.001 (2) | 0.008 (2) | −0.004 (2) |
C2A | 0.035 (3) | 0.037 (3) | 0.027 (3) | 0.000 (2) | 0.011 (2) | 0.000 (2) |
C3A | 0.040 (3) | 0.032 (2) | 0.027 (2) | 0.004 (2) | 0.014 (2) | 0.001 (2) |
C4A | 0.037 (3) | 0.026 (2) | 0.024 (2) | −0.001 (2) | 0.000 (2) | −0.0017 (18) |
O3 | 0.060 (14) | 0.063 (15) | 0.061 (14) | −0.030 (11) | −0.006 (11) | 0.029 (12) |
O4 | 0.026 (13) | 0.18 (4) | 0.13 (3) | −0.032 (17) | −0.006 (14) | 0.08 (3) |
O5 | 0.041 (3) | 0.042 (3) | 0.079 (5) | −0.002 (3) | 0.016 (3) | 0.022 (3) |
O6 | 0.053 (4) | 0.053 (4) | 0.054 (4) | −0.008 (3) | 0.002 (3) | 0.025 (3) |
C1B | 0.038 (3) | 0.037 (3) | 0.024 (2) | −0.001 (2) | 0.008 (2) | −0.004 (2) |
C2B | 0.035 (3) | 0.037 (3) | 0.027 (3) | 0.000 (2) | 0.011 (2) | 0.000 (2) |
C3B | 0.040 (3) | 0.032 (2) | 0.027 (2) | 0.004 (2) | 0.014 (2) | 0.001 (2) |
C4B | 0.037 (3) | 0.026 (2) | 0.024 (2) | −0.001 (2) | 0.000 (2) | −0.0017 (18) |
O11 | 0.049 (2) | 0.0261 (17) | 0.041 (2) | 0.0094 (16) | −0.0094 (17) | −0.0145 (15) |
O10 | 0.066 (3) | 0.0210 (16) | 0.0282 (19) | −0.0058 (17) | 0.0020 (17) | 0.0002 (14) |
O005 | 0.052 (2) | 0.0265 (16) | 0.0242 (17) | 0.0116 (15) | 0.0051 (15) | −0.0057 (13) |
N00A | 0.042 (2) | 0.0140 (16) | 0.0180 (18) | 0.0027 (15) | 0.0070 (17) | −0.0005 (13) |
N00B | 0.039 (2) | 0.0230 (18) | 0.0176 (18) | 0.0033 (16) | 0.0085 (16) | 0.0010 (14) |
C00F | 0.035 (2) | 0.023 (2) | 0.021 (2) | −0.0036 (19) | 0.0094 (19) | −0.0011 (17) |
C00K | 0.042 (3) | 0.028 (2) | 0.027 (2) | −0.003 (2) | 0.008 (2) | −0.0008 (19) |
C00L | 0.040 (3) | 0.026 (2) | 0.026 (2) | 0.002 (2) | 0.012 (2) | 0.0048 (18) |
C00R | 0.050 (3) | 0.022 (2) | 0.021 (2) | 0.008 (2) | 0.011 (2) | 0.0009 (17) |
C00T | 0.056 (4) | 0.016 (2) | 0.043 (3) | 0.011 (2) | −0.011 (3) | −0.002 (2) |
C00V | 0.058 (3) | 0.018 (2) | 0.026 (2) | 0.000 (2) | 0.000 (2) | −0.0060 (18) |
C00W | 0.046 (3) | 0.026 (2) | 0.022 (2) | 0.005 (2) | 0.011 (2) | 0.0004 (18) |
C00X | 0.040 (3) | 0.036 (3) | 0.038 (3) | 0.006 (2) | 0.007 (2) | 0.013 (2) |
C00Y | 0.039 (3) | 0.022 (2) | 0.027 (2) | 0.0017 (19) | 0.010 (2) | −0.0011 (18) |
C016 | 0.061 (4) | 0.052 (4) | 0.042 (3) | 0.010 (3) | 0.005 (3) | 0.031 (3) |
C019 | 0.041 (3) | 0.028 (2) | 0.019 (2) | 0.001 (2) | 0.007 (2) | −0.0037 (18) |
C01A | 0.056 (4) | 0.021 (2) | 0.037 (3) | 0.007 (2) | −0.012 (2) | −0.007 (2) |
C01B | 0.045 (3) | 0.033 (3) | 0.029 (3) | −0.001 (2) | 0.002 (2) | 0.004 (2) |
C01D | 0.053 (3) | 0.040 (3) | 0.030 (3) | 0.010 (2) | −0.002 (2) | 0.002 (2) |
C01F | 0.065 (4) | 0.078 (5) | 0.026 (3) | 0.023 (4) | −0.003 (3) | −0.011 (3) |
C01H | 0.042 (3) | 0.0152 (19) | 0.033 (3) | 0.0046 (18) | 0.000 (2) | −0.0049 (18) |
C01I | 0.054 (4) | 0.028 (2) | 0.033 (3) | 0.005 (2) | −0.004 (2) | 0.011 (2) |
C01M | 0.045 (3) | 0.026 (2) | 0.038 (3) | 0.011 (2) | 0.012 (2) | 0.011 (2) |
C01O | 0.064 (4) | 0.034 (3) | 0.039 (3) | 0.014 (3) | 0.017 (3) | −0.004 (2) |
C01R | 0.060 (4) | 0.020 (2) | 0.084 (5) | 0.008 (3) | −0.023 (4) | −0.011 (3) |
C01S | 0.060 (4) | 0.119 (7) | 0.025 (3) | 0.038 (4) | 0.004 (3) | 0.025 (4) |
C01T | 0.052 (4) | 0.036 (3) | 0.092 (5) | 0.000 (3) | −0.008 (4) | 0.033 (3) |
C01W | 0.061 (5) | 0.020 (3) | 0.118 (7) | 0.003 (3) | −0.025 (4) | 0.001 (3) |
C01Y | 0.072 (5) | 0.108 (6) | 0.032 (3) | 0.043 (5) | 0.005 (3) | −0.002 (4) |
O002 | 0.045 (2) | 0.0270 (17) | 0.0332 (19) | 0.0072 (15) | 0.0117 (16) | −0.0085 (15) |
O007 | 0.085 (3) | 0.0212 (16) | 0.030 (2) | 0.0044 (18) | 0.016 (2) | 0.0026 (14) |
N00C | 0.050 (3) | 0.0102 (15) | 0.0232 (19) | 0.0019 (15) | 0.0103 (18) | −0.0011 (13) |
N00D | 0.035 (2) | 0.0231 (18) | 0.0217 (19) | 0.0064 (16) | 0.0080 (16) | −0.0016 (15) |
O9 | 0.080 (3) | 0.029 (2) | 0.041 (2) | 0.0076 (19) | −0.006 (2) | −0.0036 (16) |
C00G | 0.040 (3) | 0.024 (2) | 0.043 (3) | 0.001 (2) | 0.012 (2) | −0.010 (2) |
C00I | 0.038 (3) | 0.030 (2) | 0.023 (2) | 0.002 (2) | 0.014 (2) | −0.0020 (18) |
C00M | 0.036 (3) | 0.023 (2) | 0.029 (2) | 0.0009 (19) | 0.008 (2) | −0.0017 (18) |
C00S | 0.042 (3) | 0.019 (2) | 0.023 (2) | 0.0026 (19) | 0.009 (2) | −0.0003 (17) |
C010 | 0.055 (3) | 0.027 (2) | 0.028 (3) | 0.006 (2) | 0.020 (2) | 0.0023 (19) |
C012 | 0.060 (3) | 0.023 (2) | 0.020 (2) | 0.008 (2) | 0.012 (2) | −0.0017 (18) |
C013 | 0.055 (3) | 0.017 (2) | 0.033 (3) | 0.001 (2) | 0.000 (2) | 0.0019 (18) |
C015 | 0.058 (3) | 0.028 (2) | 0.028 (3) | 0.008 (2) | 0.011 (2) | −0.007 (2) |
C01C | 0.036 (3) | 0.033 (3) | 0.051 (3) | 0.004 (2) | 0.000 (2) | −0.002 (2) |
C01G | 0.041 (3) | 0.032 (3) | 0.040 (3) | −0.005 (2) | −0.001 (2) | −0.004 (2) |
C01J | 0.037 (3) | 0.018 (2) | 0.034 (3) | 0.0018 (18) | 0.008 (2) | −0.0019 (18) |
C01N | 0.041 (3) | 0.026 (2) | 0.031 (3) | 0.005 (2) | 0.006 (2) | −0.0074 (19) |
C01P | 0.072 (4) | 0.030 (3) | 0.055 (4) | 0.006 (3) | −0.004 (3) | 0.027 (3) |
C01U | 0.084 (4) | 0.018 (2) | 0.026 (3) | 0.008 (2) | 0.011 (3) | 0.0016 (19) |
C01V | 0.100 (5) | 0.026 (3) | 0.038 (3) | 0.014 (3) | −0.015 (3) | −0.007 (2) |
C01X | 0.071 (5) | 0.067 (4) | 0.038 (3) | 0.020 (4) | 0.004 (3) | 0.029 (3) |
C01Z | 0.055 (4) | 0.048 (4) | 0.115 (7) | 0.003 (3) | −0.003 (5) | 0.065 (4) |
C020 | 0.119 (7) | 0.020 (3) | 0.080 (5) | −0.004 (3) | −0.037 (5) | 0.006 (3) |
C021 | 0.066 (4) | 0.019 (2) | 0.074 (5) | −0.002 (2) | −0.022 (4) | 0.019 (3) |
C022 | 0.057 (5) | 0.099 (7) | 0.114 (8) | 0.018 (5) | 0.028 (5) | 0.086 (6) |
C023 | 0.079 (5) | 0.110 (7) | 0.035 (3) | 0.026 (5) | 0.014 (3) | 0.031 (4) |
C024 | 0.080 (6) | 0.029 (4) | 0.181 (12) | −0.002 (4) | −0.039 (7) | 0.051 (5) |
C025 | 0.098 (7) | 0.021 (3) | 0.182 (11) | −0.012 (4) | −0.073 (7) | 0.022 (5) |
C026 | 0.082 (6) | 0.144 (9) | 0.068 (6) | 0.038 (6) | 0.032 (5) | 0.066 (6) |
O8 | 0.040 (2) | 0.0313 (18) | 0.047 (2) | 0.0009 (15) | 0.0158 (17) | 0.0111 (17) |
O7 | 0.050 (2) | 0.0283 (19) | 0.048 (2) | 0.0029 (17) | 0.0038 (19) | 0.0136 (17) |
C00N | 0.055 (3) | 0.026 (2) | 0.020 (2) | 0.004 (2) | 0.004 (2) | 0.0018 (18) |
C00O | 0.038 (3) | 0.025 (2) | 0.021 (2) | 0.0039 (19) | 0.010 (2) | −0.0050 (18) |
C00Q | 0.039 (3) | 0.032 (3) | 0.026 (2) | 0.013 (2) | 0.005 (2) | 0.0046 (19) |
C00Z | 0.045 (3) | 0.022 (2) | 0.029 (3) | 0.002 (2) | 0.015 (2) | −0.0005 (19) |
C018 | 0.045 (3) | 0.028 (2) | 0.031 (3) | −0.006 (2) | 0.004 (2) | −0.003 (2) |
O1 | 0.052 (2) | 0.0222 (16) | 0.040 (2) | 0.0002 (15) | 0.0112 (18) | 0.0065 (15) |
O2 | 0.050 (2) | 0.035 (2) | 0.044 (2) | 0.0062 (17) | −0.0024 (19) | 0.0105 (17) |
C00P | 0.045 (3) | 0.031 (2) | 0.021 (2) | 0.011 (2) | 0.004 (2) | −0.002 (2) |
C00U | 0.041 (3) | 0.0185 (19) | 0.019 (2) | 0.0055 (18) | 0.0069 (19) | −0.0017 (16) |
C017 | 0.070 (4) | 0.030 (3) | 0.017 (2) | −0.011 (3) | 0.000 (2) | −0.0026 (19) |
C01E | 0.076 (4) | 0.018 (2) | 0.021 (2) | 0.009 (2) | 0.011 (3) | −0.0002 (18) |
C01L | 0.049 (3) | 0.039 (3) | 0.023 (2) | 0.010 (2) | 0.010 (2) | 0.001 (2) |
C1A—C00U | 1.393 (7) | C01T—C01W | 1.348 (11) |
C1A—C017 | 1.396 (7) | C01T—H01T | 0.9300 |
C1A—O3 | 1.41 (2) | C01W—H01W | 0.9300 |
C2A—O4 | 1.18 (3) | C01Y—H01Y | 0.9300 |
C2A—C00U | 1.390 (7) | O002—C00M | 1.372 (6) |
C2A—C01L | 1.402 (7) | O002—C015 | 1.440 (6) |
C3A—O5 | 1.279 (7) | O007—C01U | 1.425 (6) |
C3A—C00Q | 1.392 (7) | O007—H007 | 0.8200 |
C3A—C00O | 1.393 (7) | N00C—C013 | 1.488 (7) |
C4A—C00O | 1.389 (7) | N00C—C012 | 1.502 (6) |
C4A—O6 | 1.391 (8) | N00C—C00S | 1.514 (6) |
C4A—C018 | 1.396 (7) | N00C—H00H | 0.9800 |
O3—H3 | 0.8200 | N00D—C01J | 1.426 (6) |
O4—H4 | 0.8200 | N00D—C00I | 1.455 (6) |
O5—H5 | 0.8200 | N00D—C010 | 1.476 (6) |
O6—H6 | 0.8200 | O9—C021 | 1.367 (8) |
C1B—C00U | 1.393 (7) | O9—C01V | 1.438 (7) |
C1B—C017 | 1.396 (7) | C00G—C00M | 1.389 (7) |
C1B—H1B | 0.9300 | C00G—C01C | 1.392 (8) |
C2B—C00U | 1.390 (7) | C00G—H00I | 0.9300 |
C2B—C01L | 1.402 (7) | C00I—C00S | 1.510 (7) |
C2B—H2B | 0.9300 | C00I—H00J | 0.9700 |
C3B—C00Q | 1.392 (7) | C00I—H00L | 0.9700 |
C3B—C00O | 1.393 (7) | C00M—C01J | 1.417 (6) |
C3B—H3B | 0.9300 | C00S—H00M | 0.9700 |
C4B—C00O | 1.389 (7) | C00S—H00N | 0.9700 |
C4B—C018 | 1.396 (7) | C010—C012 | 1.489 (8) |
C4B—H4B | 0.9300 | C010—H01N | 0.9700 |
O11—C00T | 1.365 (7) | C010—H01O | 0.9700 |
O11—C01A | 1.433 (6) | C012—H01P | 0.9700 |
O10—C00V | 1.417 (6) | C012—H01Q | 0.9700 |
O10—H10 | 0.8200 | C013—C01U | 1.546 (7) |
O005—C00L | 1.370 (6) | C013—H01U | 0.9700 |
O005—C01O | 1.439 (6) | C013—H01V | 0.9700 |
N00A—C00R | 1.494 (5) | C015—H01X | 0.9600 |
N00A—C00Y | 1.498 (6) | C015—H01Z | 0.9600 |
N00A—C01H | 1.499 (6) | C015—H | 0.9600 |
N00A—H00A | 0.9800 | C01C—C01G | 1.377 (8) |
N00B—C00F | 1.430 (6) | C01C—H01 | 0.9300 |
N00B—C00W | 1.468 (6) | C01G—C01N | 1.391 (7) |
N00B—C019 | 1.470 (6) | C01G—H0AA | 0.9300 |
C00F—C00K | 1.383 (7) | C01J—C01N | 1.395 (7) |
C00F—C00L | 1.413 (6) | C01N—H1AA | 0.9300 |
C00K—C01B | 1.396 (7) | C01P—C01Z | 1.405 (10) |
C00K—H00K | 0.9300 | C01P—C01X | 1.410 (10) |
C00L—C01M | 1.385 (7) | C01P—C021 | 1.449 (10) |
C00R—C00W | 1.528 (7) | C01U—C01V | 1.494 (9) |
C00R—H00B | 0.9700 | C01U—H2AA | 0.9800 |
C00R—H00C | 0.9700 | C01V—H3AA | 0.9700 |
C00T—C01R | 1.379 (8) | C01V—HA | 0.9700 |
C00T—C01I | 1.414 (7) | C01X—C023 | 1.366 (10) |
C00V—C01H | 1.507 (7) | C01X—H4AA | 0.9300 |
C00V—C01A | 1.516 (8) | C01Z—C022 | 1.414 (13) |
C00V—H00V | 0.9800 | C01Z—C024 | 1.424 (13) |
C00W—H00D | 0.9700 | C020—C021 | 1.376 (9) |
C00W—H00E | 0.9700 | C020—C025 | 1.416 (13) |
C00X—C01B | 1.378 (7) | C020—H020 | 0.9300 |
C00X—C01M | 1.398 (8) | C022—C026 | 1.390 (14) |
C00X—H00X | 0.9300 | C022—H022 | 0.9300 |
C00Y—C019 | 1.508 (7) | C023—C026 | 1.402 (12) |
C00Y—H00F | 0.9700 | C023—H023 | 0.9300 |
C00Y—H00G | 0.9700 | C024—C025 | 1.344 (16) |
C016—C01S | 1.408 (10) | C024—H024 | 0.9300 |
C016—C01T | 1.412 (10) | C025—H025 | 0.9300 |
C016—C01I | 1.420 (9) | C026—H026 | 0.9300 |
C019—H01A | 0.9700 | O8—C00Z | 1.256 (6) |
C019—H01B | 0.9700 | O7—C00Z | 1.258 (7) |
C01A—H01C | 0.9700 | C00N—C018 | 1.378 (7) |
C01A—H01D | 0.9700 | C00N—C00Q | 1.379 (7) |
C01B—H01E | 0.9300 | C00N—H00O | 0.9300 |
C01D—C01F | 1.380 (8) | C00O—C00Z | 1.502 (7) |
C01D—C01I | 1.408 (8) | C00Q—H00Q | 0.9300 |
C01D—H01F | 0.9300 | C00Q—H00P | 0.9300 |
C01F—C01Y | 1.402 (9) | C018—H018 | 0.9300 |
C01F—H01G | 0.9300 | C018—H8AA | 0.9300 |
C01H—H01H | 0.9700 | O1—C00P | 1.267 (6) |
C01H—H01I | 0.9700 | O2—C00P | 1.247 (6) |
C01M—H01M | 0.9300 | C00P—C00U | 1.521 (7) |
C01O—H01J | 0.9600 | C017—C01E | 1.378 (8) |
C01O—H01K | 0.9600 | C017—H017 | 0.9300 |
C01O—H01L | 0.9600 | C017—H5AA | 0.9300 |
C01R—C01W | 1.403 (10) | C01E—C01L | 1.370 (8) |
C01R—H01R | 0.9300 | C01E—H6AA | 0.9300 |
C01S—C01Y | 1.355 (11) | C01L—H7AA | 0.9300 |
C01S—H01S | 0.9300 | C01L—HB | 0.9300 |
C00U—C1A—C017 | 119.3 (5) | C00I—N00D—C010 | 108.7 (4) |
C00U—C1A—O3 | 133.5 (10) | C021—O9—C01V | 119.4 (5) |
C017—C1A—O3 | 107.2 (10) | C00M—C00G—C01C | 120.6 (5) |
O4—C2A—C00U | 114.0 (15) | C00M—C00G—H00I | 119.7 |
O4—C2A—C01L | 125.3 (14) | C01C—C00G—H00I | 119.7 |
C00U—C2A—C01L | 119.7 (5) | N00D—C00I—C00S | 109.7 (4) |
O5—C3A—C00Q | 117.0 (5) | N00D—C00I—H00J | 109.7 |
O5—C3A—C00O | 121.4 (5) | C00S—C00I—H00J | 109.7 |
C00Q—C3A—C00O | 121.6 (5) | N00D—C00I—H00L | 109.7 |
C00O—C4A—O6 | 123.6 (5) | C00S—C00I—H00L | 109.7 |
C00O—C4A—C018 | 121.0 (5) | H00J—C00I—H00L | 108.2 |
O6—C4A—C018 | 115.2 (5) | O002—C00M—C00G | 124.5 (4) |
C1A—O3—H3 | 109.5 | O002—C00M—C01J | 115.4 (4) |
C2A—O4—H4 | 109.5 | C00G—C00M—C01J | 120.1 (5) |
C3A—O5—H5 | 109.5 | C00I—C00S—N00C | 111.4 (4) |
C4A—O6—H6 | 109.5 | C00I—C00S—H00M | 109.3 |
C00U—C1B—C017 | 119.3 (5) | N00C—C00S—H00M | 109.3 |
C00U—C1B—H1B | 120.4 | C00I—C00S—H00N | 109.3 |
C017—C1B—H1B | 120.4 | N00C—C00S—H00N | 109.3 |
C00U—C2B—C01L | 119.7 (5) | H00M—C00S—H00N | 108.0 |
C00U—C2B—H2B | 120.1 | N00D—C010—C012 | 110.4 (4) |
C01L—C2B—H2B | 120.1 | N00D—C010—H01N | 109.6 |
C00Q—C3B—C00O | 121.6 (5) | C012—C010—H01N | 109.6 |
C00Q—C3B—H3B | 119.2 | N00D—C010—H01O | 109.6 |
C00O—C3B—H3B | 119.2 | C012—C010—H01O | 109.6 |
C00O—C4B—C018 | 121.0 (5) | H01N—C010—H01O | 108.1 |
C00O—C4B—H4B | 119.5 | C010—C012—N00C | 112.9 (4) |
C018—C4B—H4B | 119.5 | C010—C012—H01P | 109.0 |
C00T—O11—C01A | 119.1 (4) | N00C—C012—H01P | 109.0 |
C00V—O10—H10 | 109.5 | C010—C012—H01Q | 109.0 |
C00L—O005—C01O | 117.8 (4) | N00C—C012—H01Q | 109.0 |
C00R—N00A—C00Y | 110.6 (3) | H01P—C012—H01Q | 107.8 |
C00R—N00A—C01H | 111.9 (4) | N00C—C013—C01U | 113.5 (5) |
C00Y—N00A—C01H | 108.2 (4) | N00C—C013—H01U | 108.9 |
C00R—N00A—H00A | 108.7 | C01U—C013—H01U | 108.9 |
C00Y—N00A—H00A | 108.7 | N00C—C013—H01V | 108.9 |
C01H—N00A—H00A | 108.7 | C01U—C013—H01V | 108.9 |
C00F—N00B—C00W | 115.1 (4) | H01U—C013—H01V | 107.7 |
C00F—N00B—C019 | 115.2 (4) | O002—C015—H01X | 109.5 |
C00W—N00B—C019 | 107.9 (4) | O002—C015—H01Z | 109.5 |
C00K—C00F—C00L | 118.5 (5) | H01X—C015—H01Z | 109.5 |
C00K—C00F—N00B | 122.8 (4) | O002—C015—H | 109.5 |
C00L—C00F—N00B | 118.5 (4) | H01X—C015—H | 109.5 |
C00F—C00K—C01B | 121.4 (5) | H01Z—C015—H | 109.5 |
C00F—C00K—H00K | 119.3 | C01G—C01C—C00G | 120.0 (5) |
C01B—C00K—H00K | 119.3 | C01G—C01C—H01 | 120.0 |
O005—C00L—C01M | 124.2 (4) | C00G—C01C—H01 | 120.0 |
O005—C00L—C00F | 115.8 (4) | C01C—C01G—C01N | 119.8 (5) |
C01M—C00L—C00F | 119.9 (5) | C01C—C01G—H0AA | 120.1 |
N00A—C00R—C00W | 111.2 (4) | C01N—C01G—H0AA | 120.1 |
N00A—C00R—H00B | 109.4 | C01N—C01J—C00M | 117.8 (5) |
C00W—C00R—H00B | 109.4 | C01N—C01J—N00D | 123.7 (4) |
N00A—C00R—H00C | 109.4 | C00M—C01J—N00D | 118.4 (4) |
C00W—C00R—H00C | 109.4 | C01G—C01N—C01J | 121.7 (5) |
H00B—C00R—H00C | 108.0 | C01G—C01N—H1AA | 119.1 |
O11—C00T—C01R | 125.3 (5) | C01J—C01N—H1AA | 119.1 |
O11—C00T—C01I | 114.6 (5) | C01Z—C01P—C01X | 120.5 (8) |
C01R—C00T—C01I | 120.1 (6) | C01Z—C01P—C021 | 117.9 (7) |
O10—C00V—C01H | 111.5 (4) | C01X—C01P—C021 | 121.6 (6) |
O10—C00V—C01A | 112.4 (4) | O007—C01U—C01V | 112.8 (4) |
C01H—C00V—C01A | 109.2 (5) | O007—C01U—C013 | 110.1 (4) |
O10—C00V—H00V | 107.9 | C01V—C01U—C013 | 109.8 (5) |
C01H—C00V—H00V | 107.9 | O007—C01U—H2AA | 108.0 |
C01A—C00V—H00V | 107.9 | C01V—C01U—H2AA | 108.0 |
N00B—C00W—C00R | 110.0 (4) | C013—C01U—H2AA | 108.0 |
N00B—C00W—H00D | 109.7 | O9—C01V—C01U | 107.5 (5) |
C00R—C00W—H00D | 109.7 | O9—C01V—H3AA | 110.2 |
N00B—C00W—H00E | 109.7 | C01U—C01V—H3AA | 110.2 |
C00R—C00W—H00E | 109.7 | O9—C01V—HA | 110.2 |
H00D—C00W—H00E | 108.2 | C01U—C01V—HA | 110.2 |
C01B—C00X—C01M | 119.7 (5) | H3AA—C01V—HA | 108.5 |
C01B—C00X—H00X | 120.2 | C023—C01X—C01P | 119.9 (7) |
C01M—C00X—H00X | 120.2 | C023—C01X—H4AA | 120.1 |
N00A—C00Y—C019 | 112.1 (4) | C01P—C01X—H4AA | 120.1 |
N00A—C00Y—H00F | 109.2 | C01P—C01Z—C022 | 118.0 (8) |
C019—C00Y—H00F | 109.2 | C01P—C01Z—C024 | 119.9 (10) |
N00A—C00Y—H00G | 109.2 | C022—C01Z—C024 | 122.0 (9) |
C019—C00Y—H00G | 109.2 | C021—C020—C025 | 117.9 (9) |
H00F—C00Y—H00G | 107.9 | C021—C020—H020 | 121.1 |
C01S—C016—C01T | 120.9 (7) | C025—C020—H020 | 121.1 |
C01S—C016—C01I | 118.4 (7) | O9—C021—C020 | 125.4 (8) |
C01T—C016—C01I | 120.7 (7) | O9—C021—C01P | 113.3 (6) |
N00B—C019—C00Y | 109.6 (4) | C020—C021—C01P | 121.3 (7) |
N00B—C019—H01A | 109.8 | C026—C022—C01Z | 121.4 (8) |
C00Y—C019—H01A | 109.8 | C026—C022—H022 | 119.3 |
N00B—C019—H01B | 109.8 | C01Z—C022—H022 | 119.3 |
C00Y—C019—H01B | 109.8 | C01X—C023—C026 | 121.4 (9) |
H01A—C019—H01B | 108.2 | C01X—C023—H023 | 119.3 |
O11—C01A—C00V | 106.7 (4) | C026—C023—H023 | 119.3 |
O11—C01A—H01C | 110.4 | C025—C024—C01Z | 119.8 (9) |
C00V—C01A—H01C | 110.4 | C025—C024—H024 | 120.1 |
O11—C01A—H01D | 110.4 | C01Z—C024—H024 | 120.1 |
C00V—C01A—H01D | 110.4 | C024—C025—C020 | 123.0 (9) |
H01C—C01A—H01D | 108.6 | C024—C025—H025 | 118.5 |
C00X—C01B—C00K | 119.9 (5) | C020—C025—H025 | 118.5 |
C00X—C01B—H01E | 120.1 | C022—C026—C023 | 118.8 (9) |
C00K—C01B—H01E | 120.1 | C022—C026—H026 | 120.6 |
C01F—C01D—C01I | 119.5 (6) | C023—C026—H026 | 120.6 |
C01F—C01D—H01F | 120.3 | C018—C00N—C00Q | 120.3 (5) |
C01I—C01D—H01F | 120.3 | C018—C00N—H00O | 119.8 |
C01D—C01F—C01Y | 120.2 (7) | C00Q—C00N—H00O | 119.8 |
C01D—C01F—H01G | 119.9 | C4A—C00O—C3A | 117.8 (4) |
C01Y—C01F—H01G | 119.9 | C4B—C00O—C3B | 117.8 (4) |
N00A—C01H—C00V | 115.1 (4) | C4B—C00O—C00Z | 120.6 (5) |
N00A—C01H—H01H | 108.5 | C4A—C00O—C00Z | 120.6 (5) |
C00V—C01H—H01H | 108.5 | C3A—C00O—C00Z | 121.4 (4) |
N00A—C01H—H01I | 108.5 | C3B—C00O—C00Z | 121.4 (4) |
C00V—C01H—H01I | 108.5 | C00N—C00Q—C3A | 119.4 (5) |
H01H—C01H—H01I | 107.5 | C00N—C00Q—C3B | 119.4 (5) |
C01D—C01I—C00T | 121.7 (5) | C00N—C00Q—H00Q | 120.3 |
C01D—C01I—C016 | 120.0 (6) | C3A—C00Q—H00Q | 120.3 |
C00T—C01I—C016 | 118.2 (5) | C00N—C00Q—H00P | 120.3 |
C00L—C01M—C00X | 120.6 (5) | C3B—C00Q—H00P | 120.3 |
C00L—C01M—H01M | 119.7 | O8—C00Z—O7 | 122.8 (5) |
C00X—C01M—H01M | 119.7 | O8—C00Z—C00O | 118.4 (5) |
O005—C01O—H01J | 109.5 | O7—C00Z—C00O | 118.8 (4) |
O005—C01O—H01K | 109.5 | C00N—C018—C4A | 119.9 (5) |
H01J—C01O—H01K | 109.5 | C00N—C018—C4B | 119.9 (5) |
O005—C01O—H01L | 109.5 | C00N—C018—H018 | 120.1 |
H01J—C01O—H01L | 109.5 | C4A—C018—H018 | 120.1 |
H01K—C01O—H01L | 109.5 | C00N—C018—H8AA | 120.1 |
C00T—C01R—C01W | 119.7 (6) | C4B—C018—H8AA | 120.1 |
C00T—C01R—H01R | 120.1 | O2—C00P—O1 | 125.2 (5) |
C01W—C01R—H01R | 120.1 | O2—C00P—C00U | 116.5 (5) |
C01Y—C01S—C016 | 120.8 (7) | O1—C00P—C00U | 118.3 (5) |
C01Y—C01S—H01S | 119.6 | C2A—C00U—C1A | 120.1 (4) |
C016—C01S—H01S | 119.6 | C2B—C00U—C1B | 120.1 (4) |
C01W—C01T—C016 | 118.8 (7) | C2B—C00U—C00P | 120.1 (5) |
C01W—C01T—H01T | 120.6 | C2A—C00U—C00P | 120.1 (5) |
C016—C01T—H01T | 120.6 | C1A—C00U—C00P | 119.8 (5) |
C01T—C01W—C01R | 122.3 (7) | C1B—C00U—C00P | 119.8 (5) |
C01T—C01W—H01W | 118.8 | C01E—C017—C1A | 120.3 (5) |
C01R—C01W—H01W | 118.8 | C01E—C017—C1B | 120.3 (5) |
C01S—C01Y—C01F | 121.0 (7) | C01E—C017—H017 | 119.8 |
C01S—C01Y—H01Y | 119.5 | C1A—C017—H017 | 119.8 |
C01F—C01Y—H01Y | 119.5 | C01E—C017—H5AA | 119.8 |
C00M—O002—C015 | 116.4 (4) | C1B—C017—H5AA | 119.8 |
C01U—O007—H007 | 109.5 | C01L—C01E—C017 | 120.7 (5) |
C013—N00C—C012 | 111.8 (4) | C01L—C01E—H6AA | 119.6 |
C013—N00C—C00S | 108.9 (4) | C017—C01E—H6AA | 119.6 |
C012—N00C—C00S | 110.9 (3) | C01E—C01L—C2A | 119.9 (5) |
C013—N00C—H00H | 108.4 | C01E—C01L—C2B | 119.9 (5) |
C012—N00C—H00H | 108.4 | C01E—C01L—H7AA | 120.1 |
C00S—N00C—H00H | 108.4 | C2A—C01L—H7AA | 120.1 |
C01J—N00D—C00I | 116.3 (4) | C01E—C01L—HB | 120.1 |
C01J—N00D—C010 | 115.0 (4) | C2B—C01L—HB | 120.1 |
C00W—N00B—C00F—C00K | 114.2 (5) | N00C—C013—C01U—C01V | 174.4 (4) |
C019—N00B—C00F—C00K | −12.3 (6) | C021—O9—C01V—C01U | 169.2 (5) |
C00W—N00B—C00F—C00L | −70.2 (5) | O007—C01U—C01V—O9 | 58.3 (6) |
C019—N00B—C00F—C00L | 163.3 (4) | C013—C01U—C01V—O9 | −64.9 (6) |
C00L—C00F—C00K—C01B | 0.3 (7) | C01Z—C01P—C01X—C023 | 1.2 (9) |
N00B—C00F—C00K—C01B | 176.0 (4) | C021—C01P—C01X—C023 | −177.1 (6) |
C01O—O005—C00L—C01M | 1.0 (7) | C01X—C01P—C01Z—C022 | 0.6 (8) |
C01O—O005—C00L—C00F | −177.1 (4) | C021—C01P—C01Z—C022 | 179.0 (5) |
C00K—C00F—C00L—O005 | 177.3 (4) | C01X—C01P—C01Z—C024 | −176.8 (6) |
N00B—C00F—C00L—O005 | 1.4 (6) | C021—C01P—C01Z—C024 | 1.6 (8) |
C00K—C00F—C00L—C01M | −0.9 (7) | C01V—O9—C021—C020 | 11.5 (8) |
N00B—C00F—C00L—C01M | −176.8 (4) | C01V—O9—C021—C01P | −170.1 (5) |
C00Y—N00A—C00R—C00W | −50.9 (5) | C025—C020—C021—O9 | −177.0 (6) |
C01H—N00A—C00R—C00W | −171.6 (4) | C025—C020—C021—C01P | 4.7 (9) |
C01A—O11—C00T—C01R | −5.6 (8) | C01Z—C01P—C021—O9 | 176.2 (4) |
C01A—O11—C00T—C01I | 175.0 (4) | C01X—C01P—C021—O9 | −5.4 (7) |
C00F—N00B—C00W—C00R | 166.1 (4) | C01Z—C01P—C021—C020 | −5.3 (8) |
C019—N00B—C00W—C00R | −63.7 (5) | C01X—C01P—C021—C020 | 173.0 (6) |
N00A—C00R—C00W—N00B | 58.0 (5) | C01P—C01Z—C022—C026 | −2.5 (10) |
C00R—N00A—C00Y—C019 | 51.6 (5) | C024—C01Z—C022—C026 | 174.8 (7) |
C01H—N00A—C00Y—C019 | 174.5 (4) | C01P—C01X—C023—C026 | −1.2 (10) |
C00F—N00B—C019—C00Y | −166.1 (4) | C01P—C01Z—C024—C025 | 2.6 (10) |
C00W—N00B—C019—C00Y | 63.7 (5) | C022—C01Z—C024—C025 | −174.7 (7) |
N00A—C00Y—C019—N00B | −58.5 (5) | C01Z—C024—C025—C020 | −3.3 (12) |
C00T—O11—C01A—C00V | −166.5 (4) | C021—C020—C025—C024 | −0.4 (11) |
O10—C00V—C01A—O11 | −57.0 (5) | C01Z—C022—C026—C023 | 2.6 (11) |
C01H—C00V—C01A—O11 | 67.3 (5) | C01X—C023—C026—C022 | −0.7 (12) |
C01M—C00X—C01B—C00K | −1.9 (8) | C018—C4B—C00O—C3B | 2.2 (7) |
C00F—C00K—C01B—C00X | 1.1 (8) | C018—C4B—C00O—C00Z | 177.4 (4) |
C01I—C01D—C01F—C01Y | 1.4 (9) | O6—C4A—C00O—C3A | 176.2 (5) |
C00R—N00A—C01H—C00V | −57.6 (5) | C018—C4A—C00O—C3A | 2.2 (7) |
C00Y—N00A—C01H—C00V | −179.7 (4) | O6—C4A—C00O—C00Z | −8.6 (8) |
O10—C00V—C01H—N00A | −49.2 (5) | C018—C4A—C00O—C00Z | 177.4 (4) |
C01A—C00V—C01H—N00A | −174.1 (4) | O5—C3A—C00O—C4A | 176.9 (6) |
C01F—C01D—C01I—C00T | 176.3 (5) | C00Q—C3A—C00O—C4A | −1.1 (7) |
C01F—C01D—C01I—C016 | −1.4 (8) | O5—C3A—C00O—C00Z | 1.8 (8) |
O11—C00T—C01I—C01D | 4.6 (7) | C00Q—C3A—C00O—C00Z | −176.3 (4) |
C01R—C00T—C01I—C01D | −174.8 (5) | C00Q—C3B—C00O—C4B | −1.1 (7) |
O11—C00T—C01I—C016 | −177.7 (5) | C00Q—C3B—C00O—C00Z | −176.3 (4) |
C01R—C00T—C01I—C016 | 2.9 (8) | C018—C00N—C00Q—C3A | −0.5 (7) |
C01S—C016—C01I—C01D | 0.1 (8) | C018—C00N—C00Q—C3B | −0.5 (7) |
C01T—C016—C01I—C01D | 178.1 (5) | O5—C3A—C00Q—C00N | −177.8 (6) |
C01S—C016—C01I—C00T | −177.7 (5) | C00O—C3A—C00Q—C00N | 0.3 (7) |
C01T—C016—C01I—C00T | 0.3 (8) | C00O—C3B—C00Q—C00N | 0.3 (7) |
O005—C00L—C01M—C00X | −177.9 (4) | C4B—C00O—C00Z—O8 | 178.1 (4) |
C00F—C00L—C01M—C00X | 0.1 (7) | C4A—C00O—C00Z—O8 | 178.1 (4) |
C01B—C00X—C01M—C00L | 1.3 (8) | C3A—C00O—C00Z—O8 | −6.9 (7) |
O11—C00T—C01R—C01W | 175.6 (6) | C3B—C00O—C00Z—O8 | −6.9 (7) |
C01I—C00T—C01R—C01W | −5.1 (9) | C4B—C00O—C00Z—O7 | −1.9 (7) |
C01T—C016—C01S—C01Y | −176.6 (6) | C4A—C00O—C00Z—O7 | −1.9 (7) |
C01I—C016—C01S—C01Y | 1.5 (9) | C3A—C00O—C00Z—O7 | 173.2 (4) |
C01S—C016—C01T—C01W | 176.7 (6) | C3B—C00O—C00Z—O7 | 173.2 (4) |
C01I—C016—C01T—C01W | −1.4 (8) | C00Q—C00N—C018—C4A | 1.5 (7) |
C016—C01T—C01W—C01R | −0.8 (10) | C00Q—C00N—C018—C4B | 1.5 (7) |
C00T—C01R—C01W—C01T | 4.1 (10) | C00O—C4A—C018—C00N | −2.4 (7) |
C016—C01S—C01Y—C01F | −1.6 (11) | O6—C4A—C018—C00N | −176.9 (5) |
C01D—C01F—C01Y—C01S | 0.2 (11) | C00O—C4B—C018—C00N | −2.4 (7) |
C01J—N00D—C00I—C00S | 164.2 (4) | C01L—C2B—C00U—C1B | −0.8 (7) |
C010—N00D—C00I—C00S | −64.1 (5) | C01L—C2B—C00U—C00P | 178.5 (4) |
C015—O002—C00M—C00G | −2.2 (7) | O4—C2A—C00U—C1A | 168 (2) |
C015—O002—C00M—C01J | 176.7 (4) | C01L—C2A—C00U—C1A | −0.8 (7) |
C01C—C00G—C00M—O002 | 177.6 (5) | O4—C2A—C00U—C00P | −12 (2) |
C01C—C00G—C00M—C01J | −1.2 (7) | C01L—C2A—C00U—C00P | 178.5 (4) |
N00D—C00I—C00S—N00C | 58.2 (5) | C017—C1A—C00U—C2A | 0.8 (7) |
C013—N00C—C00S—C00I | −172.8 (4) | O3—C1A—C00U—C2A | 179.9 (16) |
C012—N00C—C00S—C00I | −49.5 (5) | C017—C1A—C00U—C00P | −178.6 (4) |
C01J—N00D—C010—C012 | −164.9 (4) | O3—C1A—C00U—C00P | 0.5 (17) |
C00I—N00D—C010—C012 | 62.7 (5) | C017—C1B—C00U—C2B | 0.8 (7) |
N00D—C010—C012—N00C | −55.4 (5) | C017—C1B—C00U—C00P | −178.6 (4) |
C013—N00C—C012—C010 | 170.2 (4) | O2—C00P—C00U—C2B | −177.3 (5) |
C00S—N00C—C012—C010 | 48.6 (5) | O1—C00P—C00U—C2B | 1.5 (7) |
C012—N00C—C013—C01U | 58.5 (5) | O2—C00P—C00U—C2A | −177.3 (5) |
C00S—N00C—C013—C01U | −178.7 (4) | O1—C00P—C00U—C2A | 1.5 (7) |
C00M—C00G—C01C—C01G | −0.2 (8) | O2—C00P—C00U—C1A | 2.1 (7) |
C00G—C01C—C01G—C01N | 1.3 (8) | O1—C00P—C00U—C1A | −179.2 (4) |
O002—C00M—C01J—C01N | −177.4 (4) | O2—C00P—C00U—C1B | 2.1 (7) |
C00G—C00M—C01J—C01N | 1.6 (7) | O1—C00P—C00U—C1B | −179.2 (4) |
O002—C00M—C01J—N00D | −0.9 (6) | C00U—C1A—C017—C01E | −0.3 (7) |
C00G—C00M—C01J—N00D | 178.1 (4) | O3—C1A—C017—C01E | −179.6 (12) |
C00I—N00D—C01J—C01N | 14.1 (7) | C00U—C1B—C017—C01E | −0.3 (7) |
C010—N00D—C01J—C01N | −114.6 (5) | C1A—C017—C01E—C01L | −0.2 (7) |
C00I—N00D—C01J—C00M | −162.2 (4) | C1B—C017—C01E—C01L | −0.2 (7) |
C010—N00D—C01J—C00M | 69.1 (6) | C017—C01E—C01L—C2A | 0.2 (7) |
C01C—C01G—C01N—C01J | −0.9 (8) | C017—C01E—C01L—C2B | 0.2 (7) |
C00M—C01J—C01N—C01G | −0.6 (7) | O4—C2A—C01L—C01E | −168 (3) |
N00D—C01J—C01N—C01G | −176.9 (5) | C00U—C2A—C01L—C01E | 0.3 (7) |
N00C—C013—C01U—O007 | 49.6 (6) | C00U—C2B—C01L—C01E | 0.3 (7) |
C31H34N2O6.51 | F(000) = 1144 |
Mr = 538.76 | Dx = 1.366 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.253 (4) Å | Cell parameters from 9991 reflections |
b = 17.660 (6) Å | θ = 2.6–33.1° |
c = 13.247 (4) Å | µ = 0.10 mm−1 |
β = 95.787 (11)° | T = 100 K |
V = 2619.1 (15) Å3 | Block, colourless |
Z = 4 | 0.2 × 0.15 × 0.1 mm |
Bruker APEX-II CCD diffractometer | 8381 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.039 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0730 before and 0.0517 after correction. The Ratio of minimum to maximum transmission is 0.8974. The λ/2 correction factor is Not present. | θmax = 33.1°, θmin = 2.5° |
Tmin = 0.670, Tmax = 0.747 | h = −17→16 |
57701 measured reflections | k = −27→27 |
9884 independent reflections | l = −18→20 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.154 | w = 1/[σ2(Fo2) + (0.0749P)2 + 1.0813P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
9884 reflections | Δρmax = 0.73 e Å−3 |
365 parameters | Δρmin = −0.36 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C4A | 0.48030 (10) | 1.02456 (7) | 0.65389 (9) | 0.0198 (2) | 0.51 |
O4 | 0.38992 (16) | 1.07321 (10) | 0.65522 (14) | 0.0233 (3) | 0.51 |
H4 | 0.329978 | 1.056285 | 0.619338 | 0.035* | 0.51 |
C4B | 0.48030 (10) | 1.02456 (7) | 0.65389 (9) | 0.0198 (2) | 0.49 |
H4B | 0.417865 | 1.059966 | 0.659982 | 0.024* | 0.49 |
O5 | 0.79836 (7) | 0.44052 (5) | 0.44999 (6) | 0.01935 (16) | |
O6 | 0.44696 (9) | 0.76833 (5) | 0.29346 (7) | 0.02470 (18) | |
H6 | 0.429643 | 0.792486 | 0.344604 | 0.037* | |
O7 | 0.19998 (8) | 0.76071 (5) | 0.30373 (7) | 0.02275 (18) | |
O3 | 0.34133 (8) | 0.94259 (6) | 0.56653 (8) | 0.0283 (2) | |
H3 | 0.336552 | 0.900423 | 0.537065 | 0.042* | |
N1 | 0.68925 (8) | 0.55476 (5) | 0.53974 (7) | 0.01479 (16) | |
N2 | 0.50732 (8) | 0.65471 (5) | 0.44598 (7) | 0.01420 (16) | |
H2 | 0.538712 | 0.707046 | 0.459892 | 0.017* | |
C10 | 0.94916 (10) | 0.42525 (6) | 0.59402 (9) | 0.0192 (2) | |
H10 | 0.987172 | 0.385219 | 0.561727 | 0.023* | |
C30 | 0.10817 (10) | 0.85174 (7) | 0.44353 (9) | 0.0192 (2) | |
H30 | 0.192349 | 0.847911 | 0.443299 | 0.023* | |
C24 | −0.12239 (12) | 0.73999 (7) | 0.22053 (11) | 0.0264 (3) | |
H24 | −0.174191 | 0.718374 | 0.167148 | 0.032* | |
C16 | 0.49662 (9) | 0.61620 (6) | 0.54568 (8) | 0.01653 (18) | |
H16A | 0.453751 | 0.567579 | 0.533548 | 0.020* | |
H16B | 0.449210 | 0.648426 | 0.587809 | 0.020* | |
C27 | −0.13939 (10) | 0.85976 (8) | 0.44995 (10) | 0.0236 (2) | |
H27 | −0.223038 | 0.861360 | 0.454679 | 0.028* | |
C26 | −0.09408 (10) | 0.81438 (6) | 0.37455 (9) | 0.0193 (2) | |
C3 | 0.45521 (10) | 0.95551 (7) | 0.60341 (9) | 0.0189 (2) | |
C20 | 0.38389 (11) | 0.69907 (7) | 0.28691 (9) | 0.0201 (2) | |
H20 | 0.425131 | 0.664640 | 0.241688 | 0.024* | |
C25 | −0.17034 (11) | 0.77663 (7) | 0.29815 (11) | 0.0241 (2) | |
H25 | −0.254358 | 0.776852 | 0.300994 | 0.029* | |
O1 | 0.60415 (8) | 0.78553 (5) | 0.52590 (8) | 0.02445 (18) | |
O2 | 0.41478 (8) | 0.82201 (6) | 0.49306 (8) | 0.0293 (2) | |
C12 | 0.93841 (11) | 0.50626 (7) | 0.73941 (9) | 0.0218 (2) | |
H12 | 0.967954 | 0.521407 | 0.806067 | 0.026* | |
C14 | 0.79368 (9) | 0.52128 (6) | 0.59142 (8) | 0.01491 (18) | |
C13 | 0.83926 (10) | 0.54258 (6) | 0.68881 (9) | 0.0190 (2) | |
H13 | 0.802174 | 0.582704 | 0.721669 | 0.023* | |
C2 | 0.54724 (10) | 0.90368 (6) | 0.59274 (8) | 0.01735 (19) | |
C5 | 0.59494 (11) | 1.04125 (6) | 0.69464 (9) | 0.0199 (2) | |
H5A | 0.611070 | 1.087968 | 0.728859 | 0.024* | 0.51 |
H5B | 0.611070 | 1.087968 | 0.728859 | 0.024* | 0.49 |
C31 | 0.03199 (10) | 0.81011 (6) | 0.37204 (9) | 0.01741 (19) | |
C8 | 0.85451 (12) | 0.38026 (7) | 0.40023 (10) | 0.0244 (2) | |
H8A | 0.810367 | 0.370748 | 0.333844 | 0.037* | |
H8B | 0.854686 | 0.334309 | 0.441713 | 0.037* | |
H8C | 0.936920 | 0.394498 | 0.391085 | 0.037* | |
C6 | 0.68736 (10) | 0.98968 (7) | 0.68574 (9) | 0.0207 (2) | |
H6A | 0.766204 | 1.000970 | 0.714338 | 0.025* | |
C1 | 0.52147 (11) | 0.83188 (6) | 0.53416 (9) | 0.0204 (2) | |
C29 | 0.06095 (10) | 0.89764 (7) | 0.51322 (9) | 0.0210 (2) | |
H29 | 0.112481 | 0.926790 | 0.559302 | 0.025* | |
C15 | 0.61829 (10) | 0.60135 (6) | 0.60237 (8) | 0.01766 (19) | |
H15A | 0.659702 | 0.649979 | 0.618441 | 0.021* | |
H15B | 0.608746 | 0.574915 | 0.666957 | 0.021* | |
C11 | 0.99309 (10) | 0.44814 (7) | 0.69166 (10) | 0.0212 (2) | |
H11 | 1.060975 | 0.423610 | 0.725447 | 0.025* | |
C17 | 0.59271 (10) | 0.61335 (6) | 0.38556 (8) | 0.01636 (18) | |
H17A | 0.607467 | 0.644002 | 0.325509 | 0.020* | |
H17B | 0.556454 | 0.564780 | 0.361171 | 0.020* | |
C9 | 0.84980 (9) | 0.46096 (6) | 0.54394 (8) | 0.01584 (18) | |
C28 | −0.06397 (11) | 0.90158 (8) | 0.51647 (10) | 0.0232 (2) | |
H28 | −0.096079 | 0.933291 | 0.564892 | 0.028* | |
C7 | 0.66335 (10) | 0.92181 (6) | 0.63485 (9) | 0.0196 (2) | |
H7 | 0.726534 | 0.887027 | 0.628381 | 0.023* | |
C23 | 0.00311 (11) | 0.73366 (7) | 0.21828 (10) | 0.0238 (2) | |
H23 | 0.034919 | 0.707435 | 0.164455 | 0.029* | |
C19 | 0.38537 (9) | 0.66075 (6) | 0.38983 (9) | 0.01689 (18) | |
H19A | 0.333251 | 0.689597 | 0.431906 | 0.020* | |
H19B | 0.351382 | 0.609252 | 0.380039 | 0.020* | |
C18 | 0.71058 (9) | 0.59782 (6) | 0.44830 (8) | 0.01653 (18) | |
H18A | 0.763628 | 0.568570 | 0.407511 | 0.020* | |
H18B | 0.750574 | 0.646295 | 0.468035 | 0.020* | |
C21 | 0.25514 (11) | 0.70821 (7) | 0.24056 (10) | 0.0233 (2) | |
H21A | 0.252844 | 0.727921 | 0.170428 | 0.028* | |
H21B | 0.213089 | 0.658916 | 0.238770 | 0.028* | |
C22 | 0.07817 (10) | 0.76589 (6) | 0.29480 (9) | 0.0189 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C4A | 0.0224 (5) | 0.0198 (5) | 0.0169 (5) | 0.0051 (4) | 0.0005 (4) | 0.0001 (4) |
O4 | 0.0223 (7) | 0.0227 (8) | 0.0240 (8) | 0.0101 (6) | −0.0013 (6) | −0.0058 (6) |
C4B | 0.0224 (5) | 0.0198 (5) | 0.0169 (5) | 0.0051 (4) | 0.0005 (4) | 0.0001 (4) |
O5 | 0.0199 (4) | 0.0187 (4) | 0.0190 (4) | 0.0039 (3) | −0.0001 (3) | −0.0050 (3) |
O6 | 0.0310 (4) | 0.0188 (4) | 0.0247 (4) | −0.0001 (3) | 0.0046 (3) | 0.0017 (3) |
O7 | 0.0190 (4) | 0.0237 (4) | 0.0243 (4) | 0.0057 (3) | −0.0034 (3) | −0.0058 (3) |
O3 | 0.0195 (4) | 0.0312 (5) | 0.0331 (5) | 0.0025 (3) | −0.0030 (3) | −0.0103 (4) |
N1 | 0.0146 (4) | 0.0156 (4) | 0.0142 (4) | 0.0026 (3) | 0.0016 (3) | −0.0001 (3) |
N2 | 0.0152 (4) | 0.0117 (3) | 0.0158 (4) | 0.0011 (3) | 0.0023 (3) | −0.0002 (3) |
C10 | 0.0167 (4) | 0.0165 (4) | 0.0241 (5) | 0.0021 (3) | 0.0009 (4) | 0.0016 (4) |
C30 | 0.0161 (4) | 0.0223 (5) | 0.0183 (5) | 0.0008 (4) | −0.0023 (4) | 0.0005 (4) |
C24 | 0.0250 (5) | 0.0179 (5) | 0.0341 (7) | −0.0031 (4) | −0.0075 (5) | −0.0031 (4) |
C16 | 0.0168 (4) | 0.0175 (4) | 0.0158 (4) | 0.0020 (3) | 0.0039 (3) | 0.0017 (3) |
C27 | 0.0162 (4) | 0.0299 (6) | 0.0246 (6) | −0.0025 (4) | 0.0022 (4) | 0.0020 (4) |
C26 | 0.0173 (4) | 0.0178 (4) | 0.0222 (5) | −0.0026 (3) | −0.0010 (4) | 0.0049 (4) |
C3 | 0.0198 (5) | 0.0205 (5) | 0.0160 (5) | 0.0003 (4) | 0.0005 (4) | −0.0012 (4) |
C20 | 0.0225 (5) | 0.0191 (5) | 0.0184 (5) | 0.0041 (4) | 0.0013 (4) | 0.0001 (4) |
C25 | 0.0184 (5) | 0.0197 (5) | 0.0328 (6) | −0.0043 (4) | −0.0045 (4) | 0.0019 (4) |
O1 | 0.0240 (4) | 0.0167 (4) | 0.0332 (5) | −0.0027 (3) | 0.0053 (3) | −0.0060 (3) |
O2 | 0.0235 (4) | 0.0259 (4) | 0.0378 (5) | −0.0012 (3) | −0.0007 (4) | −0.0126 (4) |
C12 | 0.0218 (5) | 0.0220 (5) | 0.0204 (5) | 0.0000 (4) | −0.0038 (4) | 0.0015 (4) |
C14 | 0.0144 (4) | 0.0137 (4) | 0.0165 (4) | 0.0001 (3) | 0.0008 (3) | 0.0000 (3) |
C13 | 0.0200 (5) | 0.0187 (5) | 0.0176 (5) | 0.0004 (4) | −0.0017 (4) | −0.0013 (4) |
C2 | 0.0211 (5) | 0.0147 (4) | 0.0167 (5) | −0.0021 (3) | 0.0035 (4) | −0.0020 (3) |
C5 | 0.0254 (5) | 0.0161 (4) | 0.0176 (5) | 0.0003 (4) | −0.0001 (4) | −0.0009 (4) |
C31 | 0.0172 (4) | 0.0153 (4) | 0.0189 (5) | 0.0001 (3) | −0.0022 (4) | 0.0031 (3) |
C8 | 0.0287 (6) | 0.0210 (5) | 0.0238 (6) | 0.0061 (4) | 0.0039 (4) | −0.0057 (4) |
C6 | 0.0200 (5) | 0.0187 (5) | 0.0229 (5) | −0.0013 (4) | 0.0001 (4) | −0.0028 (4) |
C1 | 0.0252 (5) | 0.0157 (4) | 0.0211 (5) | −0.0038 (4) | 0.0060 (4) | −0.0033 (4) |
C29 | 0.0176 (4) | 0.0267 (5) | 0.0182 (5) | −0.0011 (4) | −0.0003 (4) | −0.0006 (4) |
C15 | 0.0182 (4) | 0.0201 (5) | 0.0148 (4) | 0.0032 (4) | 0.0024 (3) | −0.0014 (3) |
C11 | 0.0182 (5) | 0.0195 (5) | 0.0248 (5) | 0.0009 (4) | −0.0030 (4) | 0.0045 (4) |
C17 | 0.0187 (4) | 0.0161 (4) | 0.0147 (4) | 0.0039 (3) | 0.0038 (3) | 0.0000 (3) |
C9 | 0.0153 (4) | 0.0143 (4) | 0.0179 (5) | −0.0006 (3) | 0.0013 (3) | −0.0002 (3) |
C28 | 0.0192 (5) | 0.0308 (6) | 0.0200 (5) | −0.0008 (4) | 0.0034 (4) | −0.0008 (4) |
C7 | 0.0199 (5) | 0.0171 (4) | 0.0220 (5) | −0.0011 (4) | 0.0038 (4) | −0.0011 (4) |
C23 | 0.0264 (5) | 0.0168 (5) | 0.0265 (6) | 0.0008 (4) | −0.0055 (4) | −0.0032 (4) |
C19 | 0.0158 (4) | 0.0148 (4) | 0.0196 (5) | 0.0015 (3) | −0.0004 (3) | 0.0004 (3) |
C18 | 0.0161 (4) | 0.0169 (4) | 0.0171 (5) | 0.0020 (3) | 0.0040 (3) | 0.0016 (3) |
C21 | 0.0253 (5) | 0.0229 (5) | 0.0205 (5) | 0.0075 (4) | −0.0029 (4) | −0.0031 (4) |
C22 | 0.0194 (4) | 0.0149 (4) | 0.0214 (5) | 0.0019 (3) | −0.0032 (4) | 0.0013 (4) |
C4A—O4 | 1.3329 (19) | C20—C21 | 1.5241 (17) |
C4A—C5 | 1.3791 (17) | C20—H20 | 1.0000 |
C4A—C3 | 1.4057 (17) | C25—H25 | 0.9500 |
O4—H4 | 0.8400 | O1—C1 | 1.2522 (15) |
C4B—C5 | 1.3791 (17) | O2—C1 | 1.2791 (15) |
C4B—C3 | 1.4057 (17) | C12—C11 | 1.3824 (18) |
C4B—H4B | 0.9500 | C12—C13 | 1.3980 (16) |
O5—C9 | 1.3672 (14) | C12—H12 | 0.9500 |
O5—C8 | 1.4318 (14) | C14—C13 | 1.3912 (16) |
O6—C20 | 1.4124 (15) | C14—C9 | 1.4175 (15) |
O6—H6 | 0.8400 | C13—H13 | 0.9500 |
O7—C22 | 1.3669 (14) | C2—C7 | 1.4049 (16) |
O7—C21 | 1.4316 (15) | C2—C1 | 1.4996 (16) |
O3—C3 | 1.3442 (15) | C5—C6 | 1.3963 (17) |
O3—H3 | 0.8400 | C5—H5A | 0.9500 |
N1—C14 | 1.4272 (14) | C5—H5B | 0.9500 |
N1—C15 | 1.4616 (14) | C31—C22 | 1.4264 (17) |
N1—C18 | 1.4704 (14) | C8—H8A | 0.9800 |
N2—C19 | 1.4973 (14) | C8—H8B | 0.9800 |
N2—C17 | 1.5008 (14) | C8—H8C | 0.9800 |
N2—C16 | 1.5011 (14) | C6—C7 | 1.3883 (16) |
N2—H2 | 1.0000 | C6—H6A | 0.9500 |
C10—C9 | 1.3923 (15) | C29—C28 | 1.4123 (17) |
C10—C11 | 1.3971 (18) | C29—H29 | 0.9500 |
C10—H10 | 0.9500 | C15—H15A | 0.9900 |
C30—C29 | 1.3750 (17) | C15—H15B | 0.9900 |
C30—C31 | 1.4171 (16) | C11—H11 | 0.9500 |
C30—H30 | 0.9500 | C17—C18 | 1.5175 (15) |
C24—C25 | 1.371 (2) | C17—H17A | 0.9900 |
C24—C23 | 1.4199 (19) | C17—H17B | 0.9900 |
C24—H24 | 0.9500 | C28—H28 | 0.9500 |
C16—C15 | 1.5166 (16) | C7—H7 | 0.9500 |
C16—H16A | 0.9900 | C23—C22 | 1.3756 (16) |
C16—H16B | 0.9900 | C23—H23 | 0.9500 |
C27—C28 | 1.3753 (18) | C19—H19A | 0.9900 |
C27—C26 | 1.4152 (18) | C19—H19B | 0.9900 |
C27—H27 | 0.9500 | C18—H18A | 0.9900 |
C26—C31 | 1.4243 (16) | C18—H18B | 0.9900 |
C26—C25 | 1.4248 (17) | C21—H21A | 0.9900 |
C3—C2 | 1.3999 (16) | C21—H21B | 0.9900 |
C20—C19 | 1.5207 (17) | ||
O4—C4A—C5 | 122.81 (13) | C6—C5—H5A | 119.9 |
O4—C4A—C3 | 116.66 (13) | C4B—C5—H5B | 119.9 |
C5—C4A—C3 | 120.44 (10) | C6—C5—H5B | 119.9 |
C4A—O4—H4 | 109.5 | C30—C31—C26 | 119.59 (11) |
C5—C4B—C3 | 120.44 (10) | C30—C31—C22 | 121.59 (10) |
C5—C4B—H4B | 119.8 | C26—C31—C22 | 118.78 (10) |
C3—C4B—H4B | 119.8 | O5—C8—H8A | 109.5 |
C9—O5—C8 | 116.70 (9) | O5—C8—H8B | 109.5 |
C20—O6—H6 | 109.5 | H8A—C8—H8B | 109.5 |
C22—O7—C21 | 118.87 (9) | O5—C8—H8C | 109.5 |
C3—O3—H3 | 109.5 | H8A—C8—H8C | 109.5 |
C14—N1—C15 | 115.55 (9) | H8B—C8—H8C | 109.5 |
C14—N1—C18 | 114.49 (8) | C7—C6—C5 | 119.60 (11) |
C15—N1—C18 | 108.69 (9) | C7—C6—H6A | 120.2 |
C19—N2—C17 | 111.95 (8) | C5—C6—H6A | 120.2 |
C19—N2—C16 | 108.58 (8) | O1—C1—O2 | 123.19 (11) |
C17—N2—C16 | 111.17 (8) | O1—C1—C2 | 119.43 (11) |
C19—N2—H2 | 108.3 | O2—C1—C2 | 117.37 (10) |
C17—N2—H2 | 108.3 | C30—C29—C28 | 120.17 (11) |
C16—N2—H2 | 108.3 | C30—C29—H29 | 119.9 |
C9—C10—C11 | 120.14 (11) | C28—C29—H29 | 119.9 |
C9—C10—H10 | 119.9 | N1—C15—C16 | 109.50 (9) |
C11—C10—H10 | 119.9 | N1—C15—H15A | 109.8 |
C29—C30—C31 | 120.39 (11) | C16—C15—H15A | 109.8 |
C29—C30—H30 | 119.8 | N1—C15—H15B | 109.8 |
C31—C30—H30 | 119.8 | C16—C15—H15B | 109.8 |
C25—C24—C23 | 121.36 (11) | H15A—C15—H15B | 108.2 |
C25—C24—H24 | 119.3 | C12—C11—C10 | 120.42 (10) |
C23—C24—H24 | 119.3 | C12—C11—H11 | 119.8 |
N2—C16—C15 | 111.44 (9) | C10—C11—H11 | 119.8 |
N2—C16—H16A | 109.3 | N2—C17—C18 | 111.54 (9) |
C15—C16—H16A | 109.3 | N2—C17—H17A | 109.3 |
N2—C16—H16B | 109.3 | C18—C17—H17A | 109.3 |
C15—C16—H16B | 109.3 | N2—C17—H17B | 109.3 |
H16A—C16—H16B | 108.0 | C18—C17—H17B | 109.3 |
C28—C27—C26 | 120.89 (11) | H17A—C17—H17B | 108.0 |
C28—C27—H27 | 119.6 | O5—C9—C10 | 124.06 (10) |
C26—C27—H27 | 119.6 | O5—C9—C14 | 115.83 (9) |
C27—C26—C31 | 118.49 (10) | C10—C9—C14 | 120.09 (10) |
C27—C26—C25 | 122.16 (11) | C27—C28—C29 | 120.39 (12) |
C31—C26—C25 | 119.25 (11) | C27—C28—H28 | 119.8 |
O3—C3—C2 | 122.70 (11) | C29—C28—H28 | 119.8 |
O3—C3—C4B | 117.29 (10) | C6—C7—C2 | 121.15 (11) |
C2—C3—C4B | 120.01 (10) | C6—C7—H7 | 119.4 |
O3—C3—C4A | 117.29 (10) | C2—C7—H7 | 119.4 |
C2—C3—C4A | 120.01 (10) | C22—C23—C24 | 119.34 (12) |
O6—C20—C19 | 111.74 (10) | C22—C23—H23 | 120.3 |
O6—C20—C21 | 112.60 (10) | C24—C23—H23 | 120.3 |
C19—C20—C21 | 109.41 (10) | N2—C19—C20 | 113.81 (9) |
O6—C20—H20 | 107.6 | N2—C19—H19A | 108.8 |
C19—C20—H20 | 107.6 | C20—C19—H19A | 108.8 |
C21—C20—H20 | 107.6 | N2—C19—H19B | 108.8 |
C24—C25—C26 | 119.95 (11) | C20—C19—H19B | 108.8 |
C24—C25—H25 | 120.0 | H19A—C19—H19B | 107.7 |
C26—C25—H25 | 120.0 | N1—C18—C17 | 109.78 (9) |
C11—C12—C13 | 119.45 (11) | N1—C18—H18A | 109.7 |
C11—C12—H12 | 120.3 | C17—C18—H18A | 109.7 |
C13—C12—H12 | 120.3 | N1—C18—H18B | 109.7 |
C13—C14—C9 | 118.39 (10) | C17—C18—H18B | 109.7 |
C13—C14—N1 | 122.79 (10) | H18A—C18—H18B | 108.2 |
C9—C14—N1 | 118.72 (9) | O7—C21—C20 | 106.48 (9) |
C14—C13—C12 | 121.50 (11) | O7—C21—H21A | 110.4 |
C14—C13—H13 | 119.3 | C20—C21—H21A | 110.4 |
C12—C13—H13 | 119.3 | O7—C21—H21B | 110.4 |
C3—C2—C7 | 118.60 (10) | C20—C21—H21B | 110.4 |
C3—C2—C1 | 119.92 (10) | H21A—C21—H21B | 108.6 |
C7—C2—C1 | 121.45 (10) | O7—C22—C23 | 124.89 (11) |
C4B—C5—C6 | 120.19 (11) | O7—C22—C31 | 114.16 (10) |
C4A—C5—C6 | 120.19 (11) | C23—C22—C31 | 120.94 (11) |
C4A—C5—H5A | 119.9 | ||
C19—N2—C16—C15 | 174.53 (8) | C31—C30—C29—C28 | 2.28 (18) |
C17—N2—C16—C15 | 50.96 (11) | C14—N1—C15—C16 | −165.61 (9) |
C28—C27—C26—C31 | 2.93 (18) | C18—N1—C15—C16 | 64.09 (11) |
C28—C27—C26—C25 | −173.43 (12) | N2—C16—C15—N1 | −58.13 (12) |
C5—C4B—C3—O3 | 179.29 (11) | C13—C12—C11—C10 | −0.62 (18) |
C5—C4B—C3—C2 | −1.06 (18) | C9—C10—C11—C12 | 0.07 (18) |
O4—C4A—C3—O3 | −4.01 (19) | C19—N2—C17—C18 | −172.00 (8) |
C5—C4A—C3—O3 | 179.29 (11) | C16—N2—C17—C18 | −50.38 (11) |
O4—C4A—C3—C2 | 175.64 (13) | C8—O5—C9—C10 | −2.32 (16) |
C5—C4A—C3—C2 | −1.06 (18) | C8—O5—C9—C14 | 179.30 (10) |
C23—C24—C25—C26 | 4.88 (19) | C11—C10—C9—O5 | −177.59 (10) |
C27—C26—C25—C24 | 173.06 (12) | C11—C10—C9—C14 | 0.72 (17) |
C31—C26—C25—C24 | −3.27 (18) | C13—C14—C9—O5 | 177.50 (10) |
C15—N1—C14—C13 | −12.37 (15) | N1—C14—C9—O5 | 0.86 (14) |
C18—N1—C14—C13 | 115.07 (12) | C13—C14—C9—C10 | −0.95 (16) |
C15—N1—C14—C9 | 164.10 (10) | N1—C14—C9—C10 | −177.58 (10) |
C18—N1—C14—C9 | −68.46 (12) | C26—C27—C28—C29 | −2.5 (2) |
C9—C14—C13—C12 | 0.40 (17) | C30—C29—C28—C27 | −0.16 (19) |
N1—C14—C13—C12 | 176.89 (10) | C5—C6—C7—C2 | −0.56 (18) |
C11—C12—C13—C14 | 0.38 (18) | C3—C2—C7—C6 | −0.26 (17) |
O3—C3—C2—C7 | −179.31 (11) | C1—C2—C7—C6 | 177.56 (11) |
C4B—C3—C2—C7 | 1.06 (17) | C25—C24—C23—C22 | −0.93 (19) |
C4A—C3—C2—C7 | 1.06 (17) | C17—N2—C19—C20 | −56.96 (11) |
O3—C3—C2—C1 | 2.83 (18) | C16—N2—C19—C20 | 179.94 (9) |
C4B—C3—C2—C1 | −176.80 (11) | O6—C20—C19—N2 | −49.85 (12) |
C4A—C3—C2—C1 | −176.80 (11) | C21—C20—C19—N2 | −175.24 (9) |
C3—C4B—C5—C6 | 0.23 (18) | C14—N1—C18—C17 | 165.54 (9) |
O4—C4A—C5—C6 | −176.26 (14) | C15—N1—C18—C17 | −63.58 (11) |
C3—C4A—C5—C6 | 0.23 (18) | N2—C17—C18—N1 | 56.87 (11) |
C29—C30—C31—C26 | −1.77 (17) | C22—O7—C21—C20 | −164.51 (10) |
C29—C30—C31—C22 | 175.92 (11) | O6—C20—C21—O7 | −58.62 (13) |
C27—C26—C31—C30 | −0.80 (16) | C19—C20—C21—O7 | 66.27 (12) |
C25—C26—C31—C30 | 175.66 (11) | C21—O7—C22—C23 | −11.22 (17) |
C27—C26—C31—C22 | −178.56 (11) | C21—O7—C22—C31 | 170.09 (10) |
C25—C26—C31—C22 | −2.10 (16) | C24—C23—C22—O7 | 176.78 (11) |
C4B—C5—C6—C7 | 0.57 (18) | C24—C23—C22—C31 | −4.62 (18) |
C4A—C5—C6—C7 | 0.57 (18) | C30—C31—C22—O7 | 7.11 (16) |
C3—C2—C1—O1 | −179.29 (11) | C26—C31—C22—O7 | −175.18 (10) |
C7—C2—C1—O1 | 2.91 (17) | C30—C31—C22—C23 | −171.63 (11) |
C3—C2—C1—O2 | 2.05 (17) | C26—C31—C22—C23 | 6.08 (16) |
C7—C2—C1—O2 | −175.75 (11) |
C31H34.55N2O6.14 | F(000) = 1135 |
Mr = 533.39 | Dx = 1.359 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.176 (4) Å | Cell parameters from 9929 reflections |
b = 17.608 (5) Å | θ = 2.8–30.5° |
c = 13.305 (4) Å | µ = 0.10 mm−1 |
β = 95.426 (10)° | T = 100 K |
V = 2606.6 (14) Å3 | Plate, colourless |
Z = 4 | 0.2 × 0.15 × 0.15 mm |
Bruker APEX-II CCD diffractometer | 6366 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 0.0722 before and 0.0532 after correction. The Ratio of minimum to maximum transmission is 0.9047. The λ/2 correction factor is Not present. | θmax = 30.5°, θmin = 2.6° |
Tmin = 0.675, Tmax = 0.746 | h = −15→14 |
39100 measured reflections | k = −24→25 |
7888 independent reflections | l = −17→18 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0397P)2 + 2.2439P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
7888 reflections | Δρmax = 0.35 e Å−3 |
366 parameters | Δρmin = −0.65 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C5A | 0.40763 (17) | −0.04064 (10) | 0.30364 (13) | 0.0238 (3) | 0.14 |
O4 | 0.3631 (10) | −0.0977 (6) | 0.2450 (8) | 0.034 (2) | 0.14 |
H4 | 0.397039 | −0.138499 | 0.264051 | 0.052* | 0.14 |
C5B | 0.40763 (17) | −0.04064 (10) | 0.30364 (13) | 0.0238 (3) | 0.86 |
H5B | 0.389136 | −0.086854 | 0.268720 | 0.029* | 0.86 |
O7 | 0.80427 (11) | 0.24051 (7) | 0.69463 (10) | 0.0258 (3) | |
O5 | 0.19882 (11) | 0.55784 (7) | 0.55085 (9) | 0.0228 (3) | |
O6 | 0.55637 (13) | 0.22913 (7) | 0.70199 (11) | 0.0288 (3) | |
H6 | 0.572454 | 0.207752 | 0.648449 | 0.043* | |
O2 | 0.59475 (12) | 0.17652 (7) | 0.50613 (10) | 0.0287 (3) | |
O1 | 0.40503 (12) | 0.21362 (7) | 0.47443 (11) | 0.0274 (3) | |
O3 | 0.66636 (12) | 0.05358 (9) | 0.43128 (11) | 0.0328 (3) | |
H3 | 0.671935 | 0.095859 | 0.460595 | 0.049* | 0.77 (5) |
N2 | 0.49559 (12) | 0.34538 (7) | 0.55390 (10) | 0.0172 (3) | |
H2 | 0.465517 | 0.292704 | 0.539006 | 0.021* | |
N1 | 0.31223 (12) | 0.44496 (8) | 0.46062 (10) | 0.0179 (3) | |
C28 | 1.07337 (16) | 0.09698 (10) | 0.48756 (13) | 0.0241 (3) | |
H28 | 1.106492 | 0.064563 | 0.440282 | 0.029* | |
C27 | 1.14819 (16) | 0.13801 (10) | 0.55502 (13) | 0.0241 (3) | |
H27 | 1.232705 | 0.134961 | 0.552396 | 0.029* | |
C26 | 1.10125 (15) | 0.18480 (9) | 0.62846 (13) | 0.0212 (3) | |
C31 | 0.97456 (15) | 0.19025 (9) | 0.62900 (13) | 0.0194 (3) | |
C22 | 0.92676 (16) | 0.23500 (9) | 0.70534 (13) | 0.0217 (3) | |
C21 | 0.74598 (17) | 0.29121 (10) | 0.75886 (13) | 0.0259 (4) | |
H21A | 0.786908 | 0.341130 | 0.762658 | 0.031* | |
H21B | 0.747509 | 0.270029 | 0.827893 | 0.031* | |
C20 | 0.61746 (16) | 0.29959 (9) | 0.71212 (13) | 0.0227 (3) | |
H20 | 0.573665 | 0.332509 | 0.757731 | 0.027* | |
C19 | 0.61707 (15) | 0.33997 (9) | 0.61062 (13) | 0.0200 (3) | |
H19A | 0.649539 | 0.391877 | 0.622197 | 0.024* | |
H19B | 0.671383 | 0.312506 | 0.568545 | 0.024* | |
C17 | 0.50737 (15) | 0.38508 (9) | 0.45520 (12) | 0.0201 (3) | |
H17A | 0.556470 | 0.353523 | 0.413211 | 0.024* | |
H17B | 0.549488 | 0.434059 | 0.468283 | 0.024* | |
C18 | 0.38598 (15) | 0.39954 (10) | 0.39825 (12) | 0.0206 (3) | |
H18A | 0.396383 | 0.426836 | 0.334612 | 0.025* | |
H18B | 0.345521 | 0.350593 | 0.381026 | 0.025* | |
C14 | 0.20782 (15) | 0.47872 (9) | 0.40863 (12) | 0.0187 (3) | |
C9 | 0.14944 (15) | 0.53823 (9) | 0.45649 (13) | 0.0195 (3) | |
C10 | 0.05021 (16) | 0.57413 (9) | 0.40611 (14) | 0.0230 (3) | |
H10 | 0.010590 | 0.613653 | 0.438524 | 0.028* | |
C11 | 0.00884 (16) | 0.55229 (10) | 0.30836 (14) | 0.0254 (4) | |
H11 | −0.059036 | 0.576972 | 0.274506 | 0.031* | |
C8 | 0.14113 (18) | 0.61823 (10) | 0.60046 (14) | 0.0273 (4) | |
H8A | 0.141465 | 0.664441 | 0.559449 | 0.041* | |
H8B | 0.184548 | 0.627633 | 0.666777 | 0.041* | |
H8C | 0.058005 | 0.603811 | 0.609019 | 0.041* | |
C12 | 0.06573 (17) | 0.49504 (10) | 0.26027 (14) | 0.0260 (4) | |
H12 | 0.037830 | 0.480599 | 0.193333 | 0.031* | |
C13 | 0.16459 (16) | 0.45863 (10) | 0.31096 (13) | 0.0229 (3) | |
H13 | 0.203319 | 0.419079 | 0.277843 | 0.027* | |
C16 | 0.40729 (15) | 0.38524 (9) | 0.61370 (12) | 0.0190 (3) | |
H16A | 0.442333 | 0.433906 | 0.639489 | 0.023* | |
H16B | 0.391541 | 0.353541 | 0.672476 | 0.023* | |
C15 | 0.28995 (15) | 0.40068 (9) | 0.55054 (12) | 0.0199 (3) | |
H15A | 0.250824 | 0.351992 | 0.529723 | 0.024* | |
H15B | 0.235178 | 0.429169 | 0.591099 | 0.024* | |
C25 | 1.17652 (17) | 0.22255 (10) | 0.70547 (15) | 0.0270 (4) | |
H25 | 1.261333 | 0.221826 | 0.704027 | 0.032* | |
C24 | 1.12648 (18) | 0.25967 (10) | 0.78118 (15) | 0.0300 (4) | |
H24 | 1.177563 | 0.281352 | 0.834742 | 0.036* | |
C23 | 1.00037 (18) | 0.26672 (10) | 0.78197 (14) | 0.0271 (4) | |
H23 | 0.967299 | 0.293172 | 0.835096 | 0.032* | |
C29 | 0.94733 (16) | 0.10274 (10) | 0.48811 (13) | 0.0223 (3) | |
H29 | 0.895938 | 0.074345 | 0.441147 | 0.027* | |
C30 | 0.89907 (15) | 0.14939 (9) | 0.55655 (12) | 0.0209 (3) | |
H30 | 0.814281 | 0.154281 | 0.555251 | 0.025* | |
C6 | 0.31739 (16) | 0.01182 (10) | 0.31425 (13) | 0.0248 (3) | |
H6A | 0.237474 | 0.001884 | 0.286483 | 0.030* | |
H6B | 0.237474 | 0.001884 | 0.286483 | 0.030* | 0.78 |
C7 | 0.34467 (16) | 0.07887 (10) | 0.36569 (13) | 0.0226 (3) | |
H7 | 0.282454 | 0.114573 | 0.373356 | 0.027* | |
C2 | 0.46133 (15) | 0.09524 (9) | 0.40651 (12) | 0.0183 (3) | |
C1 | 0.48789 (16) | 0.16687 (9) | 0.46575 (13) | 0.0213 (3) | |
C4 | 0.52394 (17) | −0.02656 (10) | 0.34316 (13) | 0.0237 (3) | |
H4A | 0.585071 | −0.063037 | 0.335573 | 0.028* | 0.22 |
H4B | 0.585071 | −0.063037 | 0.335573 | 0.028* | 0.78 |
C3 | 0.55217 (16) | 0.04173 (10) | 0.39468 (12) | 0.0212 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C5A | 0.0359 (10) | 0.0174 (7) | 0.0180 (7) | −0.0024 (7) | 0.0022 (7) | −0.0004 (6) |
O4 | 0.044 (6) | 0.025 (5) | 0.034 (5) | −0.001 (4) | −0.002 (4) | −0.013 (4) |
C5B | 0.0359 (10) | 0.0174 (7) | 0.0180 (7) | −0.0024 (7) | 0.0022 (7) | −0.0004 (6) |
O7 | 0.0254 (6) | 0.0235 (6) | 0.0283 (6) | 0.0053 (5) | 0.0009 (5) | −0.0073 (5) |
O5 | 0.0253 (6) | 0.0186 (6) | 0.0248 (6) | 0.0031 (5) | 0.0040 (5) | −0.0057 (5) |
O6 | 0.0371 (8) | 0.0165 (6) | 0.0347 (7) | 0.0012 (5) | 0.0127 (6) | 0.0021 (5) |
O2 | 0.0261 (7) | 0.0249 (6) | 0.0354 (7) | −0.0013 (5) | 0.0039 (5) | −0.0106 (5) |
O1 | 0.0269 (7) | 0.0163 (5) | 0.0397 (7) | 0.0006 (5) | 0.0073 (5) | −0.0066 (5) |
O3 | 0.0237 (7) | 0.0367 (8) | 0.0368 (8) | 0.0075 (6) | −0.0032 (5) | −0.0154 (6) |
N2 | 0.0198 (6) | 0.0123 (6) | 0.0200 (6) | 0.0009 (5) | 0.0050 (5) | −0.0004 (5) |
N1 | 0.0205 (7) | 0.0156 (6) | 0.0182 (6) | 0.0025 (5) | 0.0047 (5) | −0.0013 (5) |
C28 | 0.0237 (8) | 0.0278 (9) | 0.0216 (8) | 0.0015 (7) | 0.0058 (6) | 0.0016 (7) |
C27 | 0.0195 (8) | 0.0264 (8) | 0.0266 (8) | 0.0002 (6) | 0.0040 (6) | 0.0065 (7) |
C26 | 0.0213 (8) | 0.0170 (7) | 0.0247 (8) | −0.0013 (6) | −0.0007 (6) | 0.0061 (6) |
C31 | 0.0220 (8) | 0.0139 (7) | 0.0220 (7) | 0.0010 (6) | 0.0003 (6) | 0.0042 (6) |
C22 | 0.0257 (8) | 0.0148 (7) | 0.0242 (8) | 0.0017 (6) | −0.0002 (6) | 0.0021 (6) |
C21 | 0.0346 (10) | 0.0201 (8) | 0.0228 (8) | 0.0081 (7) | 0.0022 (7) | −0.0030 (6) |
C20 | 0.0286 (9) | 0.0165 (7) | 0.0237 (8) | 0.0043 (6) | 0.0057 (7) | −0.0008 (6) |
C19 | 0.0203 (8) | 0.0148 (7) | 0.0249 (8) | 0.0013 (6) | 0.0031 (6) | −0.0002 (6) |
C17 | 0.0233 (8) | 0.0176 (7) | 0.0207 (7) | 0.0018 (6) | 0.0089 (6) | 0.0010 (6) |
C18 | 0.0232 (8) | 0.0202 (7) | 0.0191 (7) | 0.0020 (6) | 0.0059 (6) | −0.0024 (6) |
C14 | 0.0202 (7) | 0.0138 (7) | 0.0224 (7) | −0.0003 (6) | 0.0045 (6) | 0.0005 (6) |
C9 | 0.0207 (8) | 0.0142 (7) | 0.0241 (8) | −0.0028 (6) | 0.0040 (6) | −0.0001 (6) |
C10 | 0.0215 (8) | 0.0166 (7) | 0.0314 (9) | 0.0016 (6) | 0.0048 (7) | 0.0024 (6) |
C11 | 0.0230 (8) | 0.0208 (8) | 0.0318 (9) | 0.0002 (6) | −0.0014 (7) | 0.0072 (7) |
C8 | 0.0326 (10) | 0.0200 (8) | 0.0302 (9) | 0.0054 (7) | 0.0080 (7) | −0.0068 (7) |
C12 | 0.0291 (9) | 0.0235 (8) | 0.0248 (8) | −0.0025 (7) | −0.0017 (7) | 0.0028 (7) |
C13 | 0.0276 (9) | 0.0180 (7) | 0.0232 (8) | −0.0003 (6) | 0.0031 (6) | −0.0014 (6) |
C16 | 0.0226 (8) | 0.0156 (7) | 0.0199 (7) | 0.0035 (6) | 0.0075 (6) | −0.0004 (6) |
C15 | 0.0211 (8) | 0.0173 (7) | 0.0221 (7) | 0.0006 (6) | 0.0071 (6) | 0.0012 (6) |
C25 | 0.0245 (9) | 0.0195 (8) | 0.0353 (10) | −0.0041 (6) | −0.0054 (7) | 0.0046 (7) |
C24 | 0.0350 (10) | 0.0168 (8) | 0.0357 (10) | −0.0053 (7) | −0.0103 (8) | −0.0012 (7) |
C23 | 0.0360 (10) | 0.0154 (7) | 0.0287 (9) | 0.0003 (7) | −0.0026 (7) | −0.0032 (7) |
C29 | 0.0225 (8) | 0.0253 (8) | 0.0191 (7) | 0.0006 (6) | 0.0016 (6) | −0.0004 (6) |
C30 | 0.0198 (8) | 0.0211 (8) | 0.0215 (7) | 0.0022 (6) | 0.0004 (6) | 0.0018 (6) |
C6 | 0.0229 (8) | 0.0263 (9) | 0.0249 (8) | −0.0050 (7) | 0.0016 (6) | −0.0030 (7) |
C7 | 0.0229 (8) | 0.0215 (8) | 0.0239 (8) | 0.0004 (6) | 0.0052 (6) | −0.0005 (6) |
C2 | 0.0226 (8) | 0.0139 (7) | 0.0190 (7) | 0.0000 (6) | 0.0057 (6) | 0.0004 (6) |
C1 | 0.0267 (8) | 0.0152 (7) | 0.0234 (8) | −0.0014 (6) | 0.0093 (6) | −0.0017 (6) |
C4 | 0.0331 (9) | 0.0196 (8) | 0.0186 (7) | 0.0082 (7) | 0.0027 (7) | −0.0006 (6) |
C3 | 0.0237 (8) | 0.0220 (8) | 0.0177 (7) | 0.0033 (6) | 0.0014 (6) | −0.0013 (6) |
C5A—O4 | 1.339 (9) | C17—C18 | 1.512 (2) |
C5A—C4 | 1.378 (3) | C17—H17A | 0.9900 |
C5A—C6 | 1.385 (3) | C17—H17B | 0.9900 |
O4—H4 | 0.8400 | C18—H18A | 0.9900 |
C5B—C4 | 1.378 (3) | C18—H18B | 0.9900 |
C5B—C6 | 1.385 (3) | C14—C13 | 1.389 (2) |
C5B—H5B | 0.9500 | C14—C9 | 1.417 (2) |
O7—C22 | 1.366 (2) | C9—C10 | 1.392 (2) |
O7—C21 | 1.434 (2) | C10—C11 | 1.393 (3) |
O5—C9 | 1.367 (2) | C10—H10 | 0.9500 |
O5—C8 | 1.436 (2) | C11—C12 | 1.381 (3) |
O6—C20 | 1.416 (2) | C11—H11 | 0.9500 |
O6—H6 | 0.8400 | C8—H8A | 0.9800 |
O2—C1 | 1.274 (2) | C8—H8B | 0.9800 |
O1—C1 | 1.253 (2) | C8—H8C | 0.9800 |
O3—C3 | 1.339 (2) | C12—C13 | 1.395 (3) |
O3—H3 | 0.8400 | C12—H12 | 0.9500 |
N2—C19 | 1.493 (2) | C13—H13 | 0.9500 |
N2—C16 | 1.499 (2) | C16—C15 | 1.514 (2) |
N2—C17 | 1.504 (2) | C16—H16A | 0.9900 |
N2—H2 | 1.0000 | C16—H16B | 0.9900 |
N1—C14 | 1.429 (2) | C15—H15A | 0.9900 |
N1—C18 | 1.462 (2) | C15—H15B | 0.9900 |
N1—C15 | 1.469 (2) | C25—C24 | 1.364 (3) |
C28—C27 | 1.373 (3) | C25—H25 | 0.9500 |
C28—C29 | 1.413 (2) | C24—C23 | 1.416 (3) |
C28—H28 | 0.9500 | C24—H24 | 0.9500 |
C27—C26 | 1.416 (3) | C23—H23 | 0.9500 |
C27—H27 | 0.9500 | C29—C30 | 1.374 (2) |
C26—C31 | 1.420 (2) | C29—H29 | 0.9500 |
C26—C25 | 1.427 (2) | C30—H30 | 0.9500 |
C31—C30 | 1.416 (2) | C6—C7 | 1.384 (2) |
C31—C22 | 1.429 (2) | C6—H6A | 0.9500 |
C22—C23 | 1.367 (2) | C6—H6B | 0.9500 |
C21—C20 | 1.517 (3) | C7—C2 | 1.394 (2) |
C21—H21A | 0.9900 | C7—H7 | 0.9500 |
C21—H21B | 0.9900 | C2—C3 | 1.405 (2) |
C20—C19 | 1.526 (2) | C2—C1 | 1.502 (2) |
C20—H20 | 1.0000 | C4—C3 | 1.405 (2) |
C19—H19A | 0.9900 | C4—H4A | 0.9500 |
C19—H19B | 0.9900 | C4—H4B | 0.9500 |
O4—C5A—C4 | 130.0 (5) | C10—C9—C14 | 119.94 (16) |
O4—C5A—C6 | 109.0 (5) | C9—C10—C11 | 120.22 (16) |
C4—C5A—C6 | 120.73 (16) | C9—C10—H10 | 119.9 |
C5A—O4—H4 | 109.5 | C11—C10—H10 | 119.9 |
C4—C5B—C6 | 120.73 (16) | C12—C11—C10 | 120.50 (17) |
C4—C5B—H5B | 119.6 | C12—C11—H11 | 119.8 |
C6—C5B—H5B | 119.6 | C10—C11—H11 | 119.8 |
C22—O7—C21 | 119.28 (14) | O5—C8—H8A | 109.5 |
C9—O5—C8 | 116.70 (14) | O5—C8—H8B | 109.5 |
C20—O6—H6 | 109.5 | H8A—C8—H8B | 109.5 |
C3—O3—H3 | 109.5 | O5—C8—H8C | 109.5 |
C19—N2—C16 | 111.99 (13) | H8A—C8—H8C | 109.5 |
C19—N2—C17 | 108.70 (12) | H8B—C8—H8C | 109.5 |
C16—N2—C17 | 111.23 (12) | C11—C12—C13 | 119.33 (17) |
C19—N2—H2 | 108.3 | C11—C12—H12 | 120.3 |
C16—N2—H2 | 108.3 | C13—C12—H12 | 120.3 |
C17—N2—H2 | 108.3 | C14—C13—C12 | 121.66 (16) |
C14—N1—C18 | 115.55 (13) | C14—C13—H13 | 119.2 |
C14—N1—C15 | 114.94 (13) | C12—C13—H13 | 119.2 |
C18—N1—C15 | 108.67 (13) | N2—C16—C15 | 111.63 (13) |
C27—C28—C29 | 120.31 (16) | N2—C16—H16A | 109.3 |
C27—C28—H28 | 119.8 | C15—C16—H16A | 109.3 |
C29—C28—H28 | 119.8 | N2—C16—H16B | 109.3 |
C28—C27—C26 | 120.98 (16) | C15—C16—H16B | 109.3 |
C28—C27—H27 | 119.5 | H16A—C16—H16B | 108.0 |
C26—C27—H27 | 119.5 | N1—C15—C16 | 110.05 (13) |
C27—C26—C31 | 118.51 (16) | N1—C15—H15A | 109.7 |
C27—C26—C25 | 122.33 (16) | C16—C15—H15A | 109.7 |
C31—C26—C25 | 119.04 (16) | N1—C15—H15B | 109.6 |
C30—C31—C26 | 119.51 (15) | C16—C15—H15B | 109.6 |
C30—C31—C22 | 121.71 (15) | H15A—C15—H15B | 108.2 |
C26—C31—C22 | 118.74 (15) | C24—C25—C26 | 119.89 (17) |
O7—C22—C23 | 125.10 (16) | C24—C25—H25 | 120.1 |
O7—C22—C31 | 113.78 (15) | C26—C25—H25 | 120.1 |
C23—C22—C31 | 121.10 (17) | C25—C24—C23 | 121.69 (17) |
O7—C21—C20 | 106.38 (14) | C25—C24—H24 | 119.2 |
O7—C21—H21A | 110.5 | C23—C24—H24 | 119.2 |
C20—C21—H21A | 110.5 | C22—C23—C24 | 119.19 (18) |
O7—C21—H21B | 110.5 | C22—C23—H23 | 120.4 |
C20—C21—H21B | 110.5 | C24—C23—H23 | 120.4 |
H21A—C21—H21B | 108.6 | C30—C29—C28 | 120.03 (16) |
O6—C20—C21 | 112.51 (14) | C30—C29—H29 | 120.0 |
O6—C20—C19 | 111.28 (14) | C28—C29—H29 | 120.0 |
C21—C20—C19 | 109.35 (14) | C29—C30—C31 | 120.59 (16) |
O6—C20—H20 | 107.8 | C29—C30—H30 | 119.7 |
C21—C20—H20 | 107.8 | C31—C30—H30 | 119.7 |
C19—C20—H20 | 107.8 | C7—C6—C5A | 119.41 (17) |
N2—C19—C20 | 113.80 (14) | C7—C6—C5B | 119.41 (17) |
N2—C19—H19A | 108.8 | C7—C6—H6A | 120.3 |
C20—C19—H19A | 108.8 | C5A—C6—H6A | 120.3 |
N2—C19—H19B | 108.8 | C7—C6—H6B | 120.3 |
C20—C19—H19B | 108.8 | C5B—C6—H6B | 120.3 |
H19A—C19—H19B | 107.7 | C6—C7—C2 | 121.54 (16) |
N2—C17—C18 | 111.55 (13) | C6—C7—H7 | 119.2 |
N2—C17—H17A | 109.3 | C2—C7—H7 | 119.2 |
C18—C17—H17A | 109.3 | C7—C2—C3 | 118.48 (15) |
N2—C17—H17B | 109.3 | C7—C2—C1 | 120.61 (15) |
C18—C17—H17B | 109.3 | C3—C2—C1 | 120.86 (15) |
H17A—C17—H17B | 108.0 | O1—C1—O2 | 123.04 (16) |
N1—C18—C17 | 109.57 (13) | O1—C1—C2 | 119.29 (16) |
N1—C18—H18A | 109.8 | O2—C1—C2 | 117.67 (15) |
C17—C18—H18A | 109.8 | C5B—C4—C3 | 120.02 (16) |
N1—C18—H18B | 109.8 | C5A—C4—C3 | 120.02 (16) |
C17—C18—H18B | 109.8 | C5A—C4—H4A | 120.0 |
H18A—C18—H18B | 108.2 | C3—C4—H4A | 120.0 |
C13—C14—C9 | 118.34 (15) | C5B—C4—H4B | 120.0 |
C13—C14—N1 | 122.89 (15) | C3—C4—H4B | 120.0 |
C9—C14—N1 | 118.68 (15) | O3—C3—C2 | 121.94 (15) |
O5—C9—C10 | 124.16 (15) | O3—C3—C4 | 118.24 (15) |
O5—C9—C14 | 115.88 (15) | C2—C3—C4 | 119.82 (16) |
C29—C28—C27—C26 | 2.1 (3) | N1—C14—C13—C12 | −176.93 (16) |
C28—C27—C26—C31 | −1.9 (2) | C11—C12—C13—C14 | −0.3 (3) |
C28—C27—C26—C25 | 174.03 (16) | C19—N2—C16—C15 | 171.69 (13) |
C27—C26—C31—C30 | −0.2 (2) | C17—N2—C16—C15 | 49.84 (17) |
C25—C26—C31—C30 | −176.29 (15) | C14—N1—C15—C16 | −165.34 (13) |
C27—C26—C31—C22 | 177.59 (15) | C18—N1—C15—C16 | 63.42 (16) |
C25—C26—C31—C22 | 1.6 (2) | N2—C16—C15—N1 | −56.58 (17) |
C21—O7—C22—C23 | 9.1 (2) | C27—C26—C25—C24 | −172.36 (17) |
C21—O7—C22—C31 | −172.46 (14) | C31—C26—C25—C24 | 3.5 (2) |
C30—C31—C22—O7 | −6.5 (2) | C26—C25—C24—C23 | −4.7 (3) |
C26—C31—C22—O7 | 175.76 (14) | O7—C22—C23—C24 | −176.93 (16) |
C30—C31—C22—C23 | 172.06 (16) | C31—C22—C23—C24 | 4.7 (3) |
C26—C31—C22—C23 | −5.7 (2) | C25—C24—C23—C22 | 0.5 (3) |
C22—O7—C21—C20 | 165.99 (14) | C27—C28—C29—C30 | −0.2 (3) |
O7—C21—C20—O6 | 58.13 (18) | C28—C29—C30—C31 | −1.9 (3) |
O7—C21—C20—C19 | −66.06 (17) | C26—C31—C30—C29 | 2.1 (2) |
C16—N2—C19—C20 | 57.51 (17) | C22—C31—C30—C29 | −175.62 (16) |
C17—N2—C19—C20 | −179.20 (13) | O4—C5A—C6—C7 | −175.1 (5) |
O6—C20—C19—N2 | 50.18 (18) | C4—C5A—C6—C7 | −0.4 (3) |
C21—C20—C19—N2 | 175.10 (13) | C4—C5B—C6—C7 | −0.4 (3) |
C19—N2—C17—C18 | −174.33 (13) | C5A—C6—C7—C2 | 0.5 (3) |
C16—N2—C17—C18 | −50.60 (17) | C5B—C6—C7—C2 | 0.5 (3) |
C14—N1—C18—C17 | 165.12 (13) | C6—C7—C2—C3 | −0.2 (2) |
C15—N1—C18—C17 | −63.97 (17) | C6—C7—C2—C1 | −177.43 (16) |
N2—C17—C18—N1 | 57.96 (17) | C7—C2—C1—O1 | −3.2 (2) |
C18—N1—C14—C13 | 12.4 (2) | C3—C2—C1—O1 | 179.62 (16) |
C15—N1—C14—C13 | −115.44 (17) | C7—C2—C1—O2 | 175.98 (16) |
C18—N1—C14—C9 | −164.04 (14) | C3—C2—C1—O2 | −1.2 (2) |
C15—N1—C14—C9 | 68.11 (19) | C6—C5B—C4—C3 | −0.2 (3) |
C8—O5—C9—C10 | 1.6 (2) | O4—C5A—C4—C3 | 173.4 (6) |
C8—O5—C9—C14 | 179.80 (14) | C6—C5A—C4—C3 | −0.2 (3) |
C13—C14—C9—O5 | −177.31 (14) | C7—C2—C3—O3 | 179.64 (16) |
N1—C14—C9—O5 | −0.7 (2) | C1—C2—C3—O3 | −3.1 (2) |
C13—C14—C9—C10 | 1.0 (2) | C7—C2—C3—C4 | −0.4 (2) |
N1—C14—C9—C10 | 177.58 (15) | C1—C2—C3—C4 | 176.88 (15) |
O5—C9—C10—C11 | 177.45 (15) | C5B—C4—C3—O3 | −179.47 (16) |
C14—C9—C10—C11 | −0.7 (2) | C5A—C4—C3—O3 | −179.47 (16) |
C9—C10—C11—C12 | −0.1 (3) | C5B—C4—C3—C2 | 0.6 (3) |
C10—C11—C12—C13 | 0.6 (3) | C5A—C4—C3—C2 | 0.6 (3) |
C9—C14—C13—C12 | −0.5 (3) |
C31H34N2O6.47 | F(000) = 1143 |
Mr = 538.12 | Dx = 1.342 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.487 (7) Å | Cell parameters from 8319 reflections |
b = 17.514 (10) Å | θ = 2.8–28.1° |
c = 13.310 (9) Å | µ = 0.09 mm−1 |
β = 95.95 (3)° | T = 100 K |
V = 2663 (3) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.15 × 0.15 mm |
Bruker APEX-II CCD diffractometer | 4598 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.166 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1670 before and 0.1042 after correction. The Ratio of minimum to maximum transmission is 0.4631. The λ/2 correction factor is Not present. | θmax = 28.3°, θmin = 2.1° |
Tmin = 0.345, Tmax = 0.746 | h = −15→15 |
76404 measured reflections | k = −23→23 |
6567 independent reflections | l = −17→17 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.104 | H-atom parameters constrained |
wR(F2) = 0.222 | w = 1/[σ2(Fo2) + 7.6232P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.003 |
6567 reflections | Δρmax = 0.25 e Å−3 |
365 parameters | Δρmin = −0.34 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C7A | 0.3590 (5) | 0.0737 (2) | 0.3686 (3) | 0.0511 (12) | 0.47 |
O4 | 0.2889 (7) | 0.1133 (6) | 0.3796 (9) | 0.094 (3) | 0.47 |
H7A | 0.224165 | 0.092897 | 0.360615 | 0.142* | 0.47 |
C7B | 0.3590 (5) | 0.0737 (2) | 0.3686 (3) | 0.0511 (12) | 0.53 |
H7B | 0.296755 | 0.107855 | 0.377886 | 0.061* | 0.53 |
O5 | 0.2087 (3) | 0.55969 (15) | 0.55475 (19) | 0.0415 (7) | |
O7 | 0.8083 (3) | 0.24588 (16) | 0.6902 (2) | 0.0562 (9) | |
O6 | 0.5689 (3) | 0.23179 (15) | 0.7052 (2) | 0.0525 (9) | |
H6 | 0.584154 | 0.208688 | 0.652820 | 0.079* | |
O1 | 0.4120 (3) | 0.20926 (15) | 0.4791 (2) | 0.0444 (7) | |
O2 | 0.6001 (3) | 0.17639 (14) | 0.5082 (2) | 0.0403 (7) | |
O3 | 0.6738 (3) | 0.0555 (2) | 0.4306 (2) | 0.0617 (10) | |
H3 | 0.677206 | 0.097047 | 0.462264 | 0.093* | |
N1 | 0.3119 (3) | 0.44386 (17) | 0.4640 (2) | 0.0337 (7) | |
N2 | 0.4972 (3) | 0.34576 (15) | 0.5543 (2) | 0.0329 (7) | |
H2 | 0.468567 | 0.292259 | 0.542524 | 0.040* | |
C8 | 0.1580 (5) | 0.6233 (2) | 0.6032 (3) | 0.0525 (12) | |
H8A | 0.155480 | 0.667943 | 0.558636 | 0.079* | |
H8B | 0.205667 | 0.635103 | 0.666724 | 0.079* | |
H8C | 0.078373 | 0.610212 | 0.617350 | 0.079* | |
C9 | 0.1537 (4) | 0.5378 (2) | 0.4628 (3) | 0.0395 (9) | |
C14 | 0.2070 (4) | 0.4763 (2) | 0.4148 (3) | 0.0352 (8) | |
C15 | 0.2967 (4) | 0.4007 (2) | 0.5572 (3) | 0.0377 (9) | |
H15A | 0.257601 | 0.351408 | 0.539358 | 0.045* | |
H15B | 0.246418 | 0.430035 | 0.599267 | 0.045* | |
C16 | 0.4141 (4) | 0.3860 (2) | 0.6163 (3) | 0.0361 (9) | |
H16A | 0.448864 | 0.435278 | 0.640292 | 0.043* | |
H16B | 0.402605 | 0.354587 | 0.676306 | 0.043* | |
C19 | 0.6177 (4) | 0.3421 (2) | 0.6068 (3) | 0.0396 (10) | |
H19A | 0.648793 | 0.394715 | 0.614725 | 0.047* | |
H19B | 0.667954 | 0.313880 | 0.563380 | 0.047* | |
C20 | 0.6273 (5) | 0.3039 (2) | 0.7109 (3) | 0.0508 (13) | |
H20 | 0.586199 | 0.337393 | 0.756840 | 0.061* | |
C21 | 0.7527 (5) | 0.2974 (2) | 0.7546 (4) | 0.0638 (16) | |
H21A | 0.791218 | 0.347992 | 0.756157 | 0.077* | |
H21B | 0.757540 | 0.277135 | 0.824349 | 0.077* | |
C22 | 0.9281 (5) | 0.2395 (2) | 0.7012 (4) | 0.0597 (14) | |
C31 | 0.9734 (4) | 0.1925 (2) | 0.6272 (3) | 0.0496 (12) | |
C26 | 1.0990 (5) | 0.1865 (3) | 0.6276 (4) | 0.0609 (15) | |
C27 | 1.1428 (5) | 0.1383 (3) | 0.5568 (4) | 0.0630 (15) | |
H27 | 1.225112 | 0.133896 | 0.555801 | 0.076* | |
C28 | 1.0703 (4) | 0.0971 (4) | 0.4890 (4) | 0.0660 (16) | |
H28 | 1.102552 | 0.064306 | 0.442283 | 0.079* | |
C25 | 1.1709 (6) | 0.2255 (3) | 0.7040 (6) | 0.087 (2) | |
H25 | 1.253514 | 0.223851 | 0.703974 | 0.105* | |
C24 | 1.1234 (7) | 0.2653 (3) | 0.7773 (7) | 0.114 (3) | |
H24 | 1.173629 | 0.288388 | 0.829896 | 0.137* | |
C23 | 1.0013 (7) | 0.2730 (3) | 0.7769 (5) | 0.098 (3) | |
H23 | 0.969682 | 0.301274 | 0.828616 | 0.117* | |
C30 | 0.9006 (4) | 0.1510 (3) | 0.5555 (3) | 0.0457 (10) | |
H30 | 0.818029 | 0.155951 | 0.553376 | 0.055* | |
C29 | 0.9480 (4) | 0.1033 (3) | 0.4882 (3) | 0.0556 (13) | |
H29 | 0.898047 | 0.074510 | 0.441067 | 0.067* | |
C13 | 0.1582 (4) | 0.4539 (2) | 0.3189 (3) | 0.0401 (9) | |
H13 | 0.193879 | 0.413631 | 0.285425 | 0.048* | |
C12 | 0.0587 (4) | 0.4890 (3) | 0.2709 (3) | 0.0459 (10) | |
H12 | 0.027295 | 0.472856 | 0.205523 | 0.055* | |
C11 | 0.0059 (4) | 0.5478 (3) | 0.3197 (3) | 0.0507 (11) | |
H11 | −0.062554 | 0.571702 | 0.287905 | 0.061* | |
C10 | 0.0530 (4) | 0.5718 (2) | 0.4149 (3) | 0.0466 (11) | |
H10 | 0.016066 | 0.611805 | 0.447826 | 0.056* | |
C18 | 0.3795 (4) | 0.3963 (2) | 0.4000 (3) | 0.0348 (8) | |
H18A | 0.385067 | 0.422104 | 0.334492 | 0.042* | |
H18B | 0.339531 | 0.346712 | 0.386634 | 0.042* | |
C17 | 0.5007 (3) | 0.3833 (2) | 0.4530 (3) | 0.0319 (8) | |
H17A | 0.545672 | 0.350707 | 0.410060 | 0.038* | |
H17B | 0.541686 | 0.432913 | 0.462175 | 0.038* | |
C1 | 0.4965 (4) | 0.1643 (2) | 0.4695 (3) | 0.0373 (10) | |
C2 | 0.4726 (4) | 0.0924 (2) | 0.4087 (3) | 0.0372 (9) | |
C6 | 0.3348 (6) | 0.0056 (3) | 0.3151 (3) | 0.0621 (16) | |
H6A | 0.257281 | −0.006284 | 0.287511 | 0.074* | 0.47 |
H6B | 0.257281 | −0.006284 | 0.287511 | 0.074* | 0.53 |
C5 | 0.4254 (6) | −0.0436 (2) | 0.3035 (3) | 0.0662 (18) | |
H5 | 0.410357 | −0.089888 | 0.267229 | 0.079* | |
C3 | 0.5628 (5) | 0.0411 (2) | 0.3953 (3) | 0.0442 (11) | |
C4 | 0.5357 (6) | −0.0272 (2) | 0.3428 (3) | 0.0587 (15) | |
H4 | 0.596434 | −0.062712 | 0.334682 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C7A | 0.086 (4) | 0.034 (2) | 0.035 (2) | −0.026 (2) | 0.016 (2) | −0.0040 (18) |
O4 | 0.050 (5) | 0.106 (7) | 0.128 (8) | 0.024 (5) | 0.016 (5) | −0.062 (6) |
C7B | 0.086 (4) | 0.034 (2) | 0.035 (2) | −0.026 (2) | 0.016 (2) | −0.0040 (18) |
O5 | 0.0589 (19) | 0.0361 (14) | 0.0299 (14) | 0.0166 (13) | 0.0064 (13) | −0.0057 (11) |
O7 | 0.084 (3) | 0.0289 (14) | 0.0504 (18) | 0.0183 (15) | −0.0179 (17) | −0.0113 (13) |
O6 | 0.107 (3) | 0.0222 (13) | 0.0297 (15) | 0.0156 (15) | 0.0137 (16) | −0.0012 (11) |
O1 | 0.0581 (19) | 0.0278 (13) | 0.0502 (17) | −0.0043 (13) | 0.0200 (15) | −0.0130 (12) |
O2 | 0.059 (2) | 0.0277 (13) | 0.0353 (15) | −0.0082 (13) | 0.0124 (14) | −0.0091 (11) |
O3 | 0.090 (3) | 0.052 (2) | 0.0424 (18) | 0.0159 (19) | 0.0021 (18) | −0.0190 (15) |
N1 | 0.052 (2) | 0.0272 (15) | 0.0227 (14) | 0.0086 (14) | 0.0076 (14) | −0.0006 (12) |
N2 | 0.058 (2) | 0.0151 (13) | 0.0263 (15) | 0.0054 (13) | 0.0051 (14) | −0.0008 (11) |
C8 | 0.083 (4) | 0.041 (2) | 0.035 (2) | 0.024 (2) | 0.015 (2) | −0.0063 (18) |
C9 | 0.055 (3) | 0.037 (2) | 0.0285 (19) | 0.0091 (18) | 0.0100 (18) | −0.0015 (16) |
C14 | 0.045 (2) | 0.0310 (18) | 0.0298 (18) | 0.0078 (17) | 0.0070 (16) | −0.0011 (15) |
C15 | 0.060 (3) | 0.0277 (18) | 0.0273 (18) | 0.0037 (17) | 0.0118 (18) | −0.0015 (15) |
C16 | 0.064 (3) | 0.0205 (16) | 0.0250 (17) | 0.0095 (17) | 0.0105 (17) | −0.0013 (13) |
C19 | 0.063 (3) | 0.0165 (15) | 0.037 (2) | 0.0078 (17) | −0.0033 (19) | −0.0033 (14) |
C20 | 0.098 (4) | 0.0208 (17) | 0.031 (2) | 0.020 (2) | −0.005 (2) | −0.0079 (15) |
C21 | 0.111 (4) | 0.026 (2) | 0.047 (3) | 0.027 (2) | −0.028 (3) | −0.0127 (18) |
C22 | 0.079 (4) | 0.0208 (18) | 0.071 (3) | 0.014 (2) | −0.033 (3) | 0.003 (2) |
C31 | 0.070 (3) | 0.030 (2) | 0.046 (2) | 0.002 (2) | −0.011 (2) | 0.0200 (18) |
C26 | 0.066 (3) | 0.038 (2) | 0.073 (4) | −0.009 (2) | −0.018 (3) | 0.036 (2) |
C27 | 0.055 (3) | 0.075 (4) | 0.057 (3) | −0.005 (3) | 0.000 (3) | 0.038 (3) |
C28 | 0.050 (3) | 0.111 (5) | 0.038 (3) | 0.001 (3) | 0.010 (2) | 0.021 (3) |
C25 | 0.073 (4) | 0.029 (2) | 0.148 (6) | −0.008 (3) | −0.045 (4) | 0.020 (3) |
C24 | 0.114 (6) | 0.030 (3) | 0.177 (8) | 0.010 (3) | −0.079 (6) | −0.021 (4) |
C23 | 0.123 (6) | 0.031 (2) | 0.123 (6) | 0.024 (3) | −0.068 (5) | −0.028 (3) |
C30 | 0.050 (3) | 0.056 (3) | 0.030 (2) | 0.000 (2) | −0.0036 (18) | 0.0081 (19) |
C29 | 0.056 (3) | 0.086 (4) | 0.025 (2) | 0.003 (3) | 0.006 (2) | 0.000 (2) |
C13 | 0.048 (2) | 0.039 (2) | 0.034 (2) | 0.0051 (18) | 0.0051 (18) | −0.0020 (17) |
C12 | 0.051 (3) | 0.051 (3) | 0.034 (2) | 0.004 (2) | 0.0010 (19) | 0.0009 (19) |
C11 | 0.054 (3) | 0.052 (3) | 0.046 (3) | 0.014 (2) | 0.004 (2) | 0.006 (2) |
C10 | 0.057 (3) | 0.042 (2) | 0.042 (2) | 0.015 (2) | 0.011 (2) | −0.0010 (18) |
C18 | 0.049 (2) | 0.0317 (18) | 0.0248 (17) | 0.0049 (17) | 0.0105 (16) | −0.0047 (14) |
C17 | 0.047 (2) | 0.0228 (16) | 0.0267 (18) | 0.0055 (15) | 0.0079 (16) | 0.0014 (13) |
C1 | 0.068 (3) | 0.0216 (16) | 0.0255 (18) | −0.0133 (18) | 0.0191 (19) | −0.0027 (14) |
C2 | 0.071 (3) | 0.0206 (16) | 0.0221 (17) | −0.0106 (17) | 0.0170 (18) | −0.0016 (13) |
C6 | 0.114 (5) | 0.044 (3) | 0.030 (2) | −0.042 (3) | 0.014 (3) | −0.0093 (19) |
C5 | 0.155 (6) | 0.024 (2) | 0.0189 (19) | −0.026 (3) | 0.008 (3) | −0.0020 (15) |
C3 | 0.088 (4) | 0.0275 (18) | 0.0174 (17) | −0.002 (2) | 0.008 (2) | −0.0032 (14) |
C4 | 0.132 (5) | 0.0232 (19) | 0.0199 (19) | 0.011 (2) | 0.005 (2) | −0.0038 (15) |
C7A—O4 | 1.084 (8) | C21—H21B | 0.9900 |
C7A—C2 | 1.397 (7) | C22—C23 | 1.375 (7) |
C7A—C6 | 1.403 (6) | C22—C31 | 1.424 (7) |
O4—H7A | 0.8400 | C31—C30 | 1.404 (6) |
C7B—C2 | 1.397 (7) | C31—C26 | 1.445 (7) |
C7B—C6 | 1.403 (6) | C26—C27 | 1.397 (8) |
C7B—H7B | 0.9500 | C26—C25 | 1.418 (8) |
O5—C9 | 1.372 (5) | C27—C28 | 1.368 (8) |
O5—C8 | 1.441 (4) | C27—H27 | 0.9500 |
O7—C22 | 1.374 (6) | C28—C29 | 1.407 (7) |
O7—C21 | 1.438 (5) | C28—H28 | 0.9500 |
O6—C20 | 1.428 (5) | C25—C24 | 1.357 (11) |
O6—H6 | 0.8400 | C25—H25 | 0.9500 |
O1—C1 | 1.266 (5) | C24—C23 | 1.409 (10) |
O2—C1 | 1.265 (5) | C24—H24 | 0.9500 |
O3—C3 | 1.336 (6) | C23—H23 | 0.9500 |
O3—H3 | 0.8400 | C30—C29 | 1.378 (6) |
N1—C14 | 1.429 (5) | C30—H30 | 0.9500 |
N1—C18 | 1.469 (4) | C29—H29 | 0.9500 |
N1—C15 | 1.478 (5) | C13—C12 | 1.393 (6) |
N2—C19 | 1.486 (5) | C13—H13 | 0.9500 |
N2—C16 | 1.501 (5) | C12—C11 | 1.391 (6) |
N2—C17 | 1.504 (4) | C12—H12 | 0.9500 |
N2—H2 | 1.0000 | C11—C10 | 1.390 (6) |
C8—H8A | 0.9800 | C11—H11 | 0.9500 |
C8—H8B | 0.9800 | C10—H10 | 0.9500 |
C8—H8C | 0.9800 | C18—C17 | 1.511 (5) |
C9—C10 | 1.395 (6) | C18—H18A | 0.9900 |
C9—C14 | 1.423 (5) | C18—H18B | 0.9900 |
C14—C13 | 1.396 (5) | C17—H17A | 0.9900 |
C15—C16 | 1.511 (6) | C17—H17B | 0.9900 |
C15—H15A | 0.9900 | C1—C2 | 1.507 (5) |
C15—H15B | 0.9900 | C2—C3 | 1.396 (6) |
C16—H16A | 0.9900 | C6—C5 | 1.372 (8) |
C16—H16B | 0.9900 | C6—H6A | 0.9500 |
C19—C20 | 1.533 (5) | C6—H6B | 0.9500 |
C19—H19A | 0.9900 | C5—C4 | 1.350 (8) |
C19—H19B | 0.9900 | C5—H5 | 0.9500 |
C20—C21 | 1.501 (7) | C3—C4 | 1.403 (5) |
C20—H20 | 1.0000 | C4—H4 | 0.9500 |
C21—H21A | 0.9900 | ||
O4—C7A—C2 | 118.5 (6) | C25—C26—C31 | 118.3 (6) |
O4—C7A—C6 | 120.1 (7) | C28—C27—C26 | 121.7 (5) |
C2—C7A—C6 | 121.4 (5) | C28—C27—H27 | 119.1 |
C7A—O4—H7A | 109.5 | C26—C27—H27 | 119.1 |
C2—C7B—C6 | 121.4 (5) | C27—C28—C29 | 120.2 (5) |
C2—C7B—H7B | 119.3 | C27—C28—H28 | 119.9 |
C6—C7B—H7B | 119.3 | C29—C28—H28 | 119.9 |
C9—O5—C8 | 116.4 (3) | C24—C25—C26 | 121.0 (6) |
C22—O7—C21 | 119.3 (4) | C24—C25—H25 | 119.5 |
C20—O6—H6 | 109.5 | C26—C25—H25 | 119.5 |
C3—O3—H3 | 109.5 | C25—C24—C23 | 121.3 (6) |
C14—N1—C18 | 115.5 (3) | C25—C24—H24 | 119.3 |
C14—N1—C15 | 114.9 (3) | C23—C24—H24 | 119.3 |
C18—N1—C15 | 108.2 (3) | C22—C23—C24 | 119.7 (7) |
C19—N2—C16 | 112.1 (3) | C22—C23—H23 | 120.2 |
C19—N2—C17 | 109.3 (3) | C24—C23—H23 | 120.2 |
C16—N2—C17 | 111.4 (3) | C29—C30—C31 | 120.5 (5) |
C19—N2—H2 | 108.0 | C29—C30—H30 | 119.8 |
C16—N2—H2 | 108.0 | C31—C30—H30 | 119.8 |
C17—N2—H2 | 108.0 | C30—C29—C28 | 120.2 (5) |
O5—C8—H8A | 109.5 | C30—C29—H29 | 119.9 |
O5—C8—H8B | 109.5 | C28—C29—H29 | 119.9 |
H8A—C8—H8B | 109.5 | C12—C13—C14 | 121.9 (4) |
O5—C8—H8C | 109.5 | C12—C13—H13 | 119.1 |
H8A—C8—H8C | 109.5 | C14—C13—H13 | 119.1 |
H8B—C8—H8C | 109.5 | C11—C12—C13 | 119.3 (4) |
O5—C9—C10 | 124.9 (3) | C11—C12—H12 | 120.3 |
O5—C9—C14 | 115.6 (4) | C13—C12—H12 | 120.3 |
C10—C9—C14 | 119.5 (4) | C10—C11—C12 | 120.1 (4) |
C13—C14—C9 | 118.2 (4) | C10—C11—H11 | 120.0 |
C13—C14—N1 | 123.2 (3) | C12—C11—H11 | 120.0 |
C9—C14—N1 | 118.5 (3) | C11—C10—C9 | 121.0 (4) |
N1—C15—C16 | 110.3 (3) | C11—C10—H10 | 119.5 |
N1—C15—H15A | 109.6 | C9—C10—H10 | 119.5 |
C16—C15—H15A | 109.6 | N1—C18—C17 | 109.4 (3) |
N1—C15—H15B | 109.6 | N1—C18—H18A | 109.8 |
C16—C15—H15B | 109.6 | C17—C18—H18A | 109.8 |
H15A—C15—H15B | 108.1 | N1—C18—H18B | 109.8 |
N2—C16—C15 | 112.2 (3) | C17—C18—H18B | 109.8 |
N2—C16—H16A | 109.2 | H18A—C18—H18B | 108.2 |
C15—C16—H16A | 109.2 | N2—C17—C18 | 112.0 (3) |
N2—C16—H16B | 109.2 | N2—C17—H17A | 109.2 |
C15—C16—H16B | 109.2 | C18—C17—H17A | 109.2 |
H16A—C16—H16B | 107.9 | N2—C17—H17B | 109.2 |
N2—C19—C20 | 114.8 (4) | C18—C17—H17B | 109.2 |
N2—C19—H19A | 108.6 | H17A—C17—H17B | 107.9 |
C20—C19—H19A | 108.6 | O2—C1—O1 | 123.5 (3) |
N2—C19—H19B | 108.6 | O2—C1—C2 | 118.0 (4) |
C20—C19—H19B | 108.6 | O1—C1—C2 | 118.4 (4) |
H19A—C19—H19B | 107.5 | C3—C2—C7A | 118.5 (4) |
O6—C20—C21 | 112.3 (3) | C3—C2—C7B | 118.5 (4) |
O6—C20—C19 | 110.4 (3) | C3—C2—C1 | 120.7 (4) |
C21—C20—C19 | 111.1 (4) | C7A—C2—C1 | 120.8 (4) |
O6—C20—H20 | 107.6 | C7B—C2—C1 | 120.8 (4) |
C21—C20—H20 | 107.6 | C5—C6—C7A | 118.6 (5) |
C19—C20—H20 | 107.6 | C5—C6—C7B | 118.6 (5) |
O7—C21—C20 | 106.5 (3) | C5—C6—H6A | 120.7 |
O7—C21—H21A | 110.4 | C7A—C6—H6A | 120.7 |
C20—C21—H21A | 110.4 | C5—C6—H6B | 120.7 |
O7—C21—H21B | 110.4 | C7B—C6—H6B | 120.7 |
C20—C21—H21B | 110.4 | C4—C5—C6 | 121.0 (4) |
H21A—C21—H21B | 108.6 | C4—C5—H5 | 119.5 |
O7—C22—C23 | 125.0 (6) | C6—C5—H5 | 119.5 |
O7—C22—C31 | 114.0 (4) | O3—C3—C2 | 121.8 (4) |
C23—C22—C31 | 120.9 (6) | O3—C3—C4 | 119.4 (4) |
C30—C31—C22 | 122.3 (5) | C2—C3—C4 | 118.8 (5) |
C30—C31—C26 | 119.3 (5) | C5—C4—C3 | 121.7 (5) |
C22—C31—C26 | 118.4 (5) | C5—C4—H4 | 119.1 |
C27—C26—C25 | 123.5 (6) | C3—C4—H4 | 119.1 |
C27—C26—C31 | 118.1 (5) | ||
C8—O5—C9—C10 | −0.9 (6) | C26—C31—C30—C29 | 2.0 (6) |
C8—O5—C9—C14 | 178.3 (4) | C31—C30—C29—C28 | −1.6 (7) |
O5—C9—C14—C13 | −177.0 (4) | C27—C28—C29—C30 | 0.2 (8) |
C10—C9—C14—C13 | 2.3 (6) | C9—C14—C13—C12 | −1.3 (6) |
O5—C9—C14—N1 | −1.0 (5) | N1—C14—C13—C12 | −177.1 (4) |
C10—C9—C14—N1 | 178.3 (4) | C14—C13—C12—C11 | −0.2 (7) |
C18—N1—C14—C13 | 12.0 (5) | C13—C12—C11—C10 | 0.7 (7) |
C15—N1—C14—C13 | −115.1 (4) | C12—C11—C10—C9 | 0.3 (7) |
C18—N1—C14—C9 | −163.8 (3) | O5—C9—C10—C11 | 177.3 (4) |
C15—N1—C14—C9 | 69.1 (5) | C14—C9—C10—C11 | −1.8 (7) |
C14—N1—C15—C16 | −165.9 (3) | C14—N1—C18—C17 | 165.3 (3) |
C18—N1—C15—C16 | 63.4 (4) | C15—N1—C18—C17 | −64.3 (4) |
C19—N2—C16—C15 | 171.1 (3) | C19—N2—C17—C18 | −174.0 (3) |
C17—N2—C16—C15 | 48.3 (4) | C16—N2—C17—C18 | −49.6 (4) |
N1—C15—C16—N2 | −55.7 (4) | N1—C18—C17—N2 | 58.2 (4) |
C16—N2—C19—C20 | 56.8 (4) | O4—C7A—C2—C3 | 179.5 (8) |
C17—N2—C19—C20 | −179.2 (3) | C6—C7A—C2—C3 | −0.7 (6) |
N2—C19—C20—O6 | 50.4 (4) | O4—C7A—C2—C1 | 2.6 (10) |
N2—C19—C20—C21 | 175.6 (3) | C6—C7A—C2—C1 | −177.6 (4) |
C22—O7—C21—C20 | 168.5 (4) | C6—C7B—C2—C3 | −0.7 (6) |
O6—C20—C21—O7 | 58.8 (5) | C6—C7B—C2—C1 | −177.6 (4) |
C19—C20—C21—O7 | −65.4 (4) | O2—C1—C2—C3 | −0.3 (5) |
C21—O7—C22—C23 | 7.1 (7) | O1—C1—C2—C3 | 179.6 (3) |
C21—O7—C22—C31 | −174.3 (4) | O2—C1—C2—C7A | 176.5 (3) |
O7—C22—C31—C30 | −5.5 (6) | O1—C1—C2—C7A | −3.6 (5) |
C23—C22—C31—C30 | 173.1 (5) | O2—C1—C2—C7B | 176.5 (3) |
O7—C22—C31—C26 | 175.6 (4) | O1—C1—C2—C7B | −3.6 (5) |
C23—C22—C31—C26 | −5.8 (7) | O4—C7A—C6—C5 | −179.4 (9) |
C30—C31—C26—C27 | −1.0 (6) | C2—C7A—C6—C5 | 0.8 (6) |
C22—C31—C26—C27 | 178.0 (4) | C2—C7B—C6—C5 | 0.8 (6) |
C30—C31—C26—C25 | −176.7 (4) | C7A—C6—C5—C4 | 0.2 (6) |
C22—C31—C26—C25 | 2.3 (6) | C7B—C6—C5—C4 | 0.2 (6) |
C25—C26—C27—C28 | 175.0 (5) | C7A—C2—C3—O3 | 179.4 (4) |
C31—C26—C27—C28 | −0.4 (7) | C7B—C2—C3—O3 | 179.4 (4) |
C26—C27—C28—C29 | 0.8 (8) | C1—C2—C3—O3 | −3.7 (5) |
C27—C26—C25—C24 | −173.0 (5) | C7A—C2—C3—C4 | −0.4 (5) |
C31—C26—C25—C24 | 2.4 (7) | C7B—C2—C3—C4 | −0.4 (5) |
C26—C25—C24—C23 | −3.8 (10) | C1—C2—C3—C4 | 176.5 (3) |
O7—C22—C23—C24 | −176.9 (5) | C6—C5—C4—C3 | −1.2 (6) |
C31—C22—C23—C24 | 4.6 (9) | O3—C3—C4—C5 | −178.4 (4) |
C25—C24—C23—C22 | 0.3 (10) | C2—C3—C4—C5 | 1.3 (6) |
C22—C31—C30—C29 | −176.9 (4) |
C31H34N2O7 | F(000) = 1160 |
Mr = 546.60 | Dx = 1.367 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.195 (15) Å | Cell parameters from 9903 reflections |
b = 17.69 (3) Å | θ = 2.6–30.5° |
c = 13.449 (18) Å | µ = 0.10 mm−1 |
β = 94.40 (5)° | T = 100 K |
V = 2655 (7) Å3 | Plate, colourless |
Z = 4 | 0.2 × 0.1 × 0.1 mm |
Bruker APEX-II CCD diffractometer | 6474 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 0.1063 before and 0.0681 after correction. The Ratio of minimum to maximum transmission is 0.8472. The λ/2 correction factor is Not present. | θmax = 30.5°, θmin = 2.3° |
Tmin = 0.632, Tmax = 0.746 | h = −15→13 |
63575 measured reflections | k = −25→25 |
8027 independent reflections | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.099 | H-atom parameters constrained |
wR(F2) = 0.219 | w = 1/[σ2(Fo2) + (0.0253P)2 + 8.2966P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max = 0.004 |
8027 reflections | Δρmax = 0.51 e Å−3 |
375 parameters | Δρmin = −0.38 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C4A | 0.4856 (3) | 0.52516 (17) | 0.6518 (2) | 0.0230 (6) | 0.65 |
C5A | 0.5986 (3) | 0.53910 (17) | 0.6948 (2) | 0.0243 (6) | 0.35 |
O4 | 0.3923 (3) | 0.5741 (2) | 0.6523 (3) | 0.0291 (7) | 0.65 |
H4 | 0.414242 | 0.613178 | 0.684100 | 0.044* | 0.65 |
O5 | 0.6365 (6) | 0.5990 (4) | 0.7522 (5) | 0.0326 (14) | 0.35 |
H5 | 0.607295 | 0.639015 | 0.727003 | 0.049* | 0.3526 |
C4B | 0.4856 (3) | 0.52516 (17) | 0.6518 (2) | 0.0230 (6) | 0.35 |
H4B | 0.424306 | 0.561979 | 0.655386 | 0.028* | 0.35 |
C5B | 0.5986 (3) | 0.53910 (17) | 0.6948 (2) | 0.0243 (6) | 0.65 |
H5B | 0.615099 | 0.585567 | 0.728486 | 0.029* | 0.65 |
O8 | 0.7914 (2) | 0.73915 (13) | 0.69246 (19) | 0.0312 (5) | |
O6 | 0.1974 (2) | 1.05991 (12) | 0.54447 (17) | 0.0267 (5) | |
O7 | 0.5414 (2) | 0.73154 (13) | 0.6985 (2) | 0.0383 (6) | |
H7 | 0.559692 | 0.708687 | 0.647002 | 0.057* | |
O2 | 0.4202 (2) | 0.32287 (15) | 0.4948 (2) | 0.0405 (6) | |
O1 | 0.6057 (2) | 0.28288 (13) | 0.53148 (19) | 0.0340 (5) | |
O3 | 0.3473 (2) | 0.44585 (16) | 0.5633 (2) | 0.0367 (6) | |
H3A | 0.340771 | 0.402981 | 0.536555 | 0.055* | |
N2 | 0.3105 (2) | 0.94625 (13) | 0.45689 (19) | 0.0222 (5) | |
N3 | 0.4897 (2) | 0.84664 (13) | 0.55027 (18) | 0.0213 (5) | |
H3 | 0.458350 | 0.794583 | 0.535489 | 0.026* | |
C11 | 0.0097 (3) | 1.05190 (17) | 0.3056 (3) | 0.0284 (6) | |
H11 | −0.057570 | 1.076305 | 0.272322 | 0.034* | |
C10 | 0.0508 (3) | 1.07499 (16) | 0.4011 (2) | 0.0255 (6) | |
H10 | 0.011699 | 1.115313 | 0.432157 | 0.031* | |
C9 | 0.1489 (3) | 1.03949 (16) | 0.4517 (2) | 0.0224 (5) | |
C14 | 0.2072 (3) | 0.97932 (15) | 0.4051 (2) | 0.0224 (5) | |
C18 | 0.3855 (3) | 0.90048 (18) | 0.3957 (2) | 0.0271 (6) | |
H18A | 0.398075 | 0.927429 | 0.332886 | 0.032* | |
H18B | 0.345097 | 0.851872 | 0.378716 | 0.032* | |
C17 | 0.5043 (3) | 0.88587 (17) | 0.4527 (2) | 0.0269 (6) | |
H17A | 0.554405 | 0.854223 | 0.411623 | 0.032* | |
H17B | 0.546342 | 0.934540 | 0.465601 | 0.032* | |
C19 | 0.6091 (3) | 0.83955 (16) | 0.6069 (2) | 0.0252 (6) | |
H19A | 0.643565 | 0.890722 | 0.617667 | 0.030* | |
H19B | 0.663223 | 0.810805 | 0.565949 | 0.030* | |
C20 | 0.6056 (3) | 0.80049 (17) | 0.7077 (2) | 0.0270 (6) | |
H20 | 0.561830 | 0.834527 | 0.751917 | 0.032* | |
C21 | 0.7323 (3) | 0.79016 (18) | 0.7557 (2) | 0.0293 (7) | |
H21A | 0.774832 | 0.839262 | 0.760531 | 0.035* | |
H21B | 0.730334 | 0.768744 | 0.823551 | 0.035* | |
C22 | 0.9130 (3) | 0.73389 (16) | 0.7022 (2) | 0.0248 (6) | |
C31 | 0.9619 (3) | 0.68972 (15) | 0.6262 (2) | 0.0208 (5) | |
C30 | 0.8881 (3) | 0.64874 (17) | 0.5554 (2) | 0.0230 (6) | |
H30 | 0.803475 | 0.652564 | 0.555678 | 0.028* | |
C29 | 0.9368 (3) | 0.60337 (18) | 0.4859 (2) | 0.0254 (6) | |
H29 | 0.886207 | 0.574427 | 0.440528 | 0.031* | |
C28 | 1.0630 (3) | 0.60004 (19) | 0.4824 (2) | 0.0281 (6) | |
H28 | 1.097027 | 0.569200 | 0.434069 | 0.034* | |
C8 | 0.1385 (3) | 1.11992 (18) | 0.5936 (3) | 0.0306 (7) | |
H8A | 0.139506 | 1.165963 | 0.553182 | 0.046* | |
H8B | 0.180436 | 1.129283 | 0.659128 | 0.046* | |
H8C | 0.055407 | 1.105418 | 0.602092 | 0.046* | |
C12 | 0.0660 (3) | 0.99372 (18) | 0.2587 (3) | 0.0291 (6) | |
H12 | 0.038322 | 0.978385 | 0.193214 | 0.035* | |
C13 | 0.1641 (3) | 0.95787 (17) | 0.3090 (2) | 0.0285 (6) | |
H13 | 0.202559 | 0.917788 | 0.276903 | 0.034* | |
C15 | 0.2860 (3) | 0.90274 (16) | 0.5467 (2) | 0.0241 (6) | |
H15A | 0.246718 | 0.854334 | 0.526778 | 0.029* | |
H15B | 0.230889 | 0.931669 | 0.586547 | 0.029* | |
C16 | 0.4016 (3) | 0.88716 (16) | 0.6091 (2) | 0.0227 (6) | |
H16A | 0.436846 | 0.935573 | 0.633927 | 0.027* | |
H16B | 0.384396 | 0.856126 | 0.667586 | 0.027* | |
C26 | 1.0885 (3) | 0.68580 (16) | 0.6240 (2) | 0.0236 (6) | |
C25 | 1.1629 (3) | 0.72296 (18) | 0.7000 (3) | 0.0297 (7) | |
H25 | 1.247526 | 0.722512 | 0.697865 | 0.036* | |
C24 | 1.1114 (3) | 0.75934 (18) | 0.7761 (3) | 0.0330 (7) | |
H24 | 1.161656 | 0.780656 | 0.828921 | 0.040* | |
C23 | 0.9864 (3) | 0.76597 (17) | 0.7781 (3) | 0.0294 (7) | |
H23 | 0.952813 | 0.792189 | 0.830931 | 0.035* | |
C27 | 1.1363 (3) | 0.64141 (19) | 0.5488 (3) | 0.0289 (6) | |
H27 | 1.220566 | 0.640183 | 0.544221 | 0.035* | |
C6 | 0.6894 (3) | 0.48559 (19) | 0.6894 (2) | 0.0283 (6) | |
H6A | 0.767387 | 0.495429 | 0.719484 | 0.034* | 0.35 |
H6B | 0.767387 | 0.495429 | 0.719484 | 0.034* | 0.65 |
C7 | 0.6652 (3) | 0.41824 (18) | 0.6399 (2) | 0.0275 (6) | |
H7A | 0.727332 | 0.381995 | 0.636268 | 0.033* | |
C3 | 0.4606 (3) | 0.45591 (17) | 0.6021 (2) | 0.0238 (6) | |
C2 | 0.5502 (3) | 0.40221 (16) | 0.5948 (2) | 0.0238 (6) | |
C1 | 0.5248 (3) | 0.33024 (18) | 0.5371 (3) | 0.0300 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C4A | 0.0234 (14) | 0.0215 (13) | 0.0245 (14) | 0.0036 (11) | 0.0037 (11) | −0.0003 (11) |
C5A | 0.0259 (14) | 0.0212 (13) | 0.0259 (14) | 0.0006 (11) | 0.0026 (11) | −0.0002 (11) |
O4 | 0.0286 (18) | 0.0249 (16) | 0.0335 (18) | 0.0079 (14) | 0.0018 (14) | −0.0084 (14) |
O5 | 0.036 (4) | 0.026 (3) | 0.036 (4) | 0.000 (3) | 0.001 (3) | −0.003 (3) |
C4B | 0.0234 (14) | 0.0215 (13) | 0.0245 (14) | 0.0036 (11) | 0.0037 (11) | −0.0003 (11) |
C5B | 0.0259 (14) | 0.0212 (13) | 0.0259 (14) | 0.0006 (11) | 0.0026 (11) | −0.0002 (11) |
O8 | 0.0265 (11) | 0.0254 (11) | 0.0421 (13) | 0.0026 (9) | 0.0054 (10) | −0.0123 (10) |
O6 | 0.0303 (11) | 0.0201 (10) | 0.0303 (11) | 0.0049 (8) | 0.0050 (9) | −0.0061 (8) |
O7 | 0.0377 (14) | 0.0214 (11) | 0.0574 (17) | 0.0004 (10) | 0.0135 (12) | 0.0092 (11) |
O2 | 0.0339 (13) | 0.0337 (13) | 0.0547 (16) | −0.0058 (10) | 0.0072 (12) | −0.0192 (12) |
O1 | 0.0425 (14) | 0.0190 (10) | 0.0417 (14) | 0.0030 (9) | 0.0102 (11) | −0.0024 (9) |
O3 | 0.0211 (11) | 0.0441 (15) | 0.0446 (15) | 0.0002 (10) | 0.0008 (10) | −0.0157 (12) |
N2 | 0.0264 (12) | 0.0172 (10) | 0.0240 (12) | 0.0036 (9) | 0.0080 (9) | 0.0008 (9) |
N3 | 0.0267 (12) | 0.0134 (10) | 0.0248 (12) | 0.0032 (9) | 0.0077 (9) | 0.0005 (9) |
C11 | 0.0262 (15) | 0.0209 (13) | 0.0378 (17) | −0.0023 (11) | −0.0003 (12) | 0.0047 (12) |
C10 | 0.0234 (14) | 0.0170 (12) | 0.0369 (16) | −0.0009 (10) | 0.0067 (12) | 0.0009 (11) |
C9 | 0.0227 (13) | 0.0164 (12) | 0.0288 (14) | −0.0025 (10) | 0.0075 (11) | −0.0003 (10) |
C14 | 0.0260 (14) | 0.0155 (12) | 0.0266 (14) | 0.0008 (10) | 0.0070 (11) | 0.0017 (10) |
C18 | 0.0327 (16) | 0.0239 (14) | 0.0257 (14) | 0.0062 (12) | 0.0094 (12) | −0.0013 (11) |
C17 | 0.0337 (16) | 0.0205 (13) | 0.0285 (15) | 0.0042 (12) | 0.0154 (12) | 0.0033 (11) |
C19 | 0.0271 (15) | 0.0163 (12) | 0.0331 (15) | 0.0006 (11) | 0.0075 (12) | −0.0017 (11) |
C20 | 0.0310 (16) | 0.0193 (13) | 0.0317 (16) | 0.0059 (11) | 0.0079 (12) | 0.0007 (11) |
C21 | 0.0366 (17) | 0.0216 (14) | 0.0304 (16) | 0.0073 (12) | 0.0064 (13) | −0.0033 (12) |
C22 | 0.0295 (15) | 0.0141 (12) | 0.0311 (15) | −0.0002 (10) | 0.0031 (12) | 0.0012 (11) |
C31 | 0.0217 (13) | 0.0160 (11) | 0.0245 (13) | 0.0011 (10) | 0.0006 (10) | 0.0043 (10) |
C30 | 0.0189 (13) | 0.0237 (13) | 0.0260 (14) | 0.0027 (10) | −0.0009 (10) | 0.0034 (11) |
C29 | 0.0229 (14) | 0.0279 (14) | 0.0251 (14) | 0.0008 (11) | −0.0008 (11) | −0.0005 (11) |
C28 | 0.0256 (15) | 0.0332 (16) | 0.0259 (14) | 0.0021 (12) | 0.0042 (12) | 0.0017 (12) |
C8 | 0.0341 (17) | 0.0233 (14) | 0.0351 (17) | 0.0052 (12) | 0.0084 (13) | −0.0075 (12) |
C12 | 0.0328 (16) | 0.0237 (14) | 0.0304 (16) | −0.0046 (12) | 0.0004 (12) | 0.0019 (12) |
C13 | 0.0364 (17) | 0.0199 (13) | 0.0298 (15) | −0.0002 (12) | 0.0071 (13) | −0.0010 (11) |
C15 | 0.0263 (14) | 0.0194 (12) | 0.0277 (14) | 0.0019 (11) | 0.0088 (11) | 0.0021 (11) |
C16 | 0.0271 (14) | 0.0173 (12) | 0.0248 (13) | 0.0045 (10) | 0.0100 (11) | 0.0012 (10) |
C26 | 0.0235 (14) | 0.0202 (13) | 0.0267 (14) | −0.0032 (10) | 0.0008 (11) | 0.0068 (11) |
C25 | 0.0262 (15) | 0.0230 (14) | 0.0393 (17) | −0.0055 (12) | −0.0018 (13) | 0.0034 (12) |
C24 | 0.0379 (18) | 0.0202 (14) | 0.0398 (18) | −0.0074 (13) | −0.0032 (14) | −0.0046 (13) |
C23 | 0.0382 (18) | 0.0150 (12) | 0.0347 (17) | −0.0018 (12) | −0.0008 (13) | −0.0044 (11) |
C27 | 0.0213 (14) | 0.0323 (16) | 0.0333 (16) | −0.0006 (12) | 0.0038 (12) | 0.0055 (13) |
C6 | 0.0231 (14) | 0.0333 (16) | 0.0283 (15) | 0.0024 (12) | 0.0002 (11) | −0.0008 (12) |
C7 | 0.0309 (16) | 0.0239 (14) | 0.0282 (15) | 0.0056 (12) | 0.0056 (12) | 0.0016 (11) |
C3 | 0.0202 (13) | 0.0267 (14) | 0.0248 (14) | −0.0019 (11) | 0.0031 (10) | −0.0050 (11) |
C2 | 0.0296 (15) | 0.0169 (12) | 0.0257 (14) | −0.0007 (11) | 0.0072 (11) | −0.0008 (10) |
C1 | 0.0336 (17) | 0.0231 (14) | 0.0347 (17) | −0.0058 (12) | 0.0118 (13) | −0.0037 (12) |
C4A—O4 | 1.356 (4) | C19—H19A | 0.9900 |
C4A—C5A | 1.372 (5) | C19—H19B | 0.9900 |
C4A—C3 | 1.413 (4) | C20—C21 | 1.524 (5) |
C5A—O5 | 1.359 (7) | C20—H20 | 1.0000 |
C5A—C6 | 1.395 (5) | C21—H21A | 0.9900 |
O4—H4 | 0.8400 | C21—H21B | 0.9900 |
O5—H5 | 0.8400 | C22—C23 | 1.381 (5) |
C4B—C5B | 1.372 (5) | C22—C31 | 1.429 (4) |
C4B—C3 | 1.413 (4) | C31—C30 | 1.412 (4) |
C4B—H4B | 0.9500 | C31—C26 | 1.422 (4) |
C5B—C6 | 1.395 (5) | C30—C29 | 1.376 (4) |
C5B—H5B | 0.9500 | C30—H30 | 0.9500 |
O8—C22 | 1.361 (4) | C29—C28 | 1.419 (5) |
O8—C21 | 1.435 (4) | C29—H29 | 0.9500 |
O6—C9 | 1.370 (4) | C28—C27 | 1.377 (5) |
O6—C8 | 1.437 (4) | C28—H28 | 0.9500 |
O7—C20 | 1.416 (4) | C8—H8A | 0.9800 |
O7—H7 | 0.8400 | C8—H8B | 0.9800 |
O2—C1 | 1.269 (5) | C8—H8C | 0.9800 |
O1—C1 | 1.240 (4) | C12—C13 | 1.397 (5) |
O3—C3 | 1.346 (4) | C12—H12 | 0.9500 |
O3—H3A | 0.8400 | C13—H13 | 0.9500 |
N2—C14 | 1.428 (4) | C15—C16 | 1.513 (5) |
N2—C18 | 1.464 (4) | C15—H15A | 0.9900 |
N2—C15 | 1.476 (4) | C15—H15B | 0.9900 |
N3—C19 | 1.493 (4) | C16—H16A | 0.9900 |
N3—C16 | 1.494 (4) | C16—H16B | 0.9900 |
N3—C17 | 1.505 (4) | C26—C27 | 1.417 (5) |
N3—H3 | 1.0000 | C26—C25 | 1.428 (5) |
C11—C12 | 1.384 (5) | C25—C24 | 1.373 (5) |
C11—C10 | 1.392 (5) | C25—H25 | 0.9500 |
C11—H11 | 0.9500 | C24—C23 | 1.407 (5) |
C10—C9 | 1.396 (4) | C24—H24 | 0.9500 |
C10—H10 | 0.9500 | C23—H23 | 0.9500 |
C9—C14 | 1.420 (4) | C27—H27 | 0.9500 |
C14—C13 | 1.398 (5) | C6—C7 | 1.381 (5) |
C18—C17 | 1.505 (5) | C6—H6A | 0.9500 |
C18—H18A | 0.9900 | C6—H6B | 0.9500 |
C18—H18B | 0.9900 | C7—C2 | 1.409 (5) |
C17—H17A | 0.9900 | C7—H7A | 0.9500 |
C17—H17B | 0.9900 | C3—C2 | 1.390 (4) |
C19—C20 | 1.525 (5) | C2—C1 | 1.507 (5) |
O4—C4A—C5A | 124.6 (3) | C30—C31—C26 | 119.6 (3) |
O4—C4A—C3 | 115.5 (3) | C30—C31—C22 | 121.8 (3) |
C5A—C4A—C3 | 119.9 (3) | C26—C31—C22 | 118.6 (3) |
O5—C5A—C4A | 128.1 (4) | C29—C30—C31 | 121.0 (3) |
O5—C5A—C6 | 111.2 (4) | C29—C30—H30 | 119.5 |
C4A—C5A—C6 | 120.5 (3) | C31—C30—H30 | 119.5 |
C4A—O4—H4 | 109.5 | C30—C29—C28 | 119.7 (3) |
C5A—O5—H5 | 109.5 | C30—C29—H29 | 120.2 |
C5B—C4B—C3 | 119.9 (3) | C28—C29—H29 | 120.2 |
C5B—C4B—H4B | 120.1 | C27—C28—C29 | 120.1 (3) |
C3—C4B—H4B | 120.1 | C27—C28—H28 | 119.9 |
C4B—C5B—C6 | 120.5 (3) | C29—C28—H28 | 119.9 |
C4B—C5B—H5B | 119.7 | O6—C8—H8A | 109.5 |
C6—C5B—H5B | 119.7 | O6—C8—H8B | 109.5 |
C22—O8—C21 | 119.2 (3) | H8A—C8—H8B | 109.5 |
C9—O6—C8 | 116.7 (3) | O6—C8—H8C | 109.5 |
C20—O7—H7 | 109.5 | H8A—C8—H8C | 109.5 |
C3—O3—H3A | 109.5 | H8B—C8—H8C | 109.5 |
C14—N2—C18 | 115.5 (3) | C11—C12—C13 | 119.0 (3) |
C14—N2—C15 | 114.7 (2) | C11—C12—H12 | 120.5 |
C18—N2—C15 | 108.8 (2) | C13—C12—H12 | 120.5 |
C19—N3—C16 | 111.8 (2) | C12—C13—C14 | 121.8 (3) |
C19—N3—C17 | 109.3 (2) | C12—C13—H13 | 119.1 |
C16—N3—C17 | 111.2 (2) | C14—C13—H13 | 119.1 |
C19—N3—H3 | 108.1 | N2—C15—C16 | 110.1 (2) |
C16—N3—H3 | 108.1 | N2—C15—H15A | 109.6 |
C17—N3—H3 | 108.1 | C16—C15—H15A | 109.6 |
C12—C11—C10 | 120.6 (3) | N2—C15—H15B | 109.6 |
C12—C11—H11 | 119.7 | C16—C15—H15B | 109.6 |
C10—C11—H11 | 119.7 | H15A—C15—H15B | 108.1 |
C11—C10—C9 | 120.6 (3) | N3—C16—C15 | 111.4 (3) |
C11—C10—H10 | 119.7 | N3—C16—H16A | 109.3 |
C9—C10—H10 | 119.7 | C15—C16—H16A | 109.3 |
O6—C9—C10 | 124.6 (3) | N3—C16—H16B | 109.3 |
O6—C9—C14 | 115.8 (3) | C15—C16—H16B | 109.3 |
C10—C9—C14 | 119.6 (3) | H16A—C16—H16B | 108.0 |
C13—C14—C9 | 118.3 (3) | C27—C26—C31 | 118.3 (3) |
C13—C14—N2 | 123.3 (3) | C27—C26—C25 | 122.3 (3) |
C9—C14—N2 | 118.3 (3) | C31—C26—C25 | 119.4 (3) |
N2—C18—C17 | 109.4 (3) | C24—C25—C26 | 119.6 (3) |
N2—C18—H18A | 109.8 | C24—C25—H25 | 120.2 |
C17—C18—H18A | 109.8 | C26—C25—H25 | 120.2 |
N2—C18—H18B | 109.8 | C25—C24—C23 | 121.9 (3) |
C17—C18—H18B | 109.8 | C25—C24—H24 | 119.0 |
H18A—C18—H18B | 108.2 | C23—C24—H24 | 119.0 |
N3—C17—C18 | 111.8 (3) | C22—C23—C24 | 119.2 (3) |
N3—C17—H17A | 109.3 | C22—C23—H23 | 120.4 |
C18—C17—H17A | 109.3 | C24—C23—H23 | 120.4 |
N3—C17—H17B | 109.3 | C28—C27—C26 | 121.2 (3) |
C18—C17—H17B | 109.3 | C28—C27—H27 | 119.4 |
H17A—C17—H17B | 107.9 | C26—C27—H27 | 119.4 |
N3—C19—C20 | 114.1 (3) | C7—C6—C5A | 119.6 (3) |
N3—C19—H19A | 108.7 | C7—C6—C5B | 119.6 (3) |
C20—C19—H19A | 108.7 | C7—C6—H6A | 120.2 |
N3—C19—H19B | 108.7 | C5A—C6—H6A | 120.2 |
C20—C19—H19B | 108.7 | C7—C6—H6B | 120.2 |
H19A—C19—H19B | 107.6 | C5B—C6—H6B | 120.2 |
O7—C20—C21 | 112.5 (3) | C6—C7—C2 | 121.3 (3) |
O7—C20—C19 | 111.1 (3) | C6—C7—H7A | 119.3 |
C21—C20—C19 | 110.1 (3) | C2—C7—H7A | 119.3 |
O7—C20—H20 | 107.6 | O3—C3—C2 | 123.1 (3) |
C21—C20—H20 | 107.6 | O3—C3—C4B | 116.4 (3) |
C19—C20—H20 | 107.6 | C2—C3—C4B | 120.5 (3) |
O8—C21—C20 | 106.3 (3) | O3—C3—C4A | 116.4 (3) |
O8—C21—H21A | 110.5 | C2—C3—C4A | 120.5 (3) |
C20—C21—H21A | 110.5 | C3—C2—C7 | 118.2 (3) |
O8—C21—H21B | 110.5 | C3—C2—C1 | 120.3 (3) |
C20—C21—H21B | 110.5 | C7—C2—C1 | 121.5 (3) |
H21A—C21—H21B | 108.7 | O1—C1—O2 | 123.8 (3) |
O8—C22—C23 | 125.2 (3) | O1—C1—C2 | 119.5 (3) |
O8—C22—C31 | 113.8 (3) | O2—C1—C2 | 116.7 (3) |
C23—C22—C31 | 121.0 (3) | ||
O4—C4A—C5A—O5 | 6.4 (6) | N2—C14—C13—C12 | −177.1 (3) |
C3—C4A—C5A—O5 | −174.0 (5) | C14—N2—C15—C16 | −165.9 (2) |
O4—C4A—C5A—C6 | −179.2 (3) | C18—N2—C15—C16 | 63.0 (3) |
C3—C4A—C5A—C6 | 0.4 (5) | C19—N3—C16—C15 | 172.9 (2) |
C3—C4B—C5B—C6 | 0.4 (5) | C17—N3—C16—C15 | 50.3 (3) |
C12—C11—C10—C9 | −0.6 (5) | N2—C15—C16—N3 | −56.6 (3) |
C8—O6—C9—C10 | 3.0 (4) | C30—C31—C26—C27 | 1.1 (4) |
C8—O6—C9—C14 | −179.0 (3) | C22—C31—C26—C27 | 179.5 (3) |
C11—C10—C9—O6 | 178.0 (3) | C30—C31—C26—C25 | −175.6 (3) |
C11—C10—C9—C14 | 0.1 (4) | C22—C31—C26—C25 | 2.8 (4) |
O6—C9—C14—C13 | −177.8 (3) | C27—C26—C25—C24 | −174.0 (3) |
C10—C9—C14—C13 | 0.3 (4) | C31—C26—C25—C24 | 2.6 (4) |
O6—C9—C14—N2 | −0.8 (4) | C26—C25—C24—C23 | −4.7 (5) |
C10—C9—C14—N2 | 177.3 (3) | O8—C22—C23—C24 | −176.7 (3) |
C18—N2—C14—C13 | 13.4 (4) | C31—C22—C23—C24 | 4.5 (5) |
C15—N2—C14—C13 | −114.4 (3) | C25—C24—C23—C22 | 1.1 (5) |
C18—N2—C14—C9 | −163.5 (3) | C29—C28—C27—C26 | 2.3 (5) |
C15—N2—C14—C9 | 68.8 (3) | C31—C26—C27—C28 | −3.1 (4) |
C14—N2—C18—C17 | 165.9 (2) | C25—C26—C27—C28 | 173.5 (3) |
C15—N2—C18—C17 | −63.4 (3) | O5—C5A—C6—C7 | 175.5 (4) |
C19—N3—C17—C18 | −175.3 (2) | C4A—C5A—C6—C7 | 0.3 (5) |
C16—N3—C17—C18 | −51.3 (3) | C4B—C5B—C6—C7 | 0.3 (5) |
N2—C18—C17—N3 | 58.0 (3) | C5A—C6—C7—C2 | −0.2 (5) |
C16—N3—C19—C20 | 56.4 (3) | C5B—C6—C7—C2 | −0.2 (5) |
C17—N3—C19—C20 | 180.0 (2) | C5B—C4B—C3—O3 | 178.9 (3) |
N3—C19—C20—O7 | 50.0 (3) | C5B—C4B—C3—C2 | −1.1 (5) |
N3—C19—C20—C21 | 175.3 (2) | O4—C4A—C3—O3 | −1.4 (4) |
C22—O8—C21—C20 | 163.8 (3) | C5A—C4A—C3—O3 | 178.9 (3) |
O7—C20—C21—O8 | 59.6 (3) | O4—C4A—C3—C2 | 178.5 (3) |
C19—C20—C21—O8 | −64.9 (3) | C5A—C4A—C3—C2 | −1.1 (5) |
C21—O8—C22—C23 | 9.6 (5) | O3—C3—C2—C7 | −178.8 (3) |
C21—O8—C22—C31 | −171.5 (3) | C4B—C3—C2—C7 | 1.2 (4) |
O8—C22—C31—C30 | −7.0 (4) | C4A—C3—C2—C7 | 1.2 (4) |
C23—C22—C31—C30 | 172.0 (3) | O3—C3—C2—C1 | 3.2 (5) |
O8—C22—C31—C26 | 174.6 (3) | C4B—C3—C2—C1 | −176.7 (3) |
C23—C22—C31—C26 | −6.4 (4) | C4A—C3—C2—C1 | −176.7 (3) |
C26—C31—C30—C29 | 1.8 (4) | C6—C7—C2—C3 | −0.6 (5) |
C22—C31—C30—C29 | −176.6 (3) | C6—C7—C2—C1 | 177.3 (3) |
C31—C30—C29—C28 | −2.7 (5) | C3—C2—C1—O1 | −179.9 (3) |
C30—C29—C28—C27 | 0.7 (5) | C7—C2—C1—O1 | 2.2 (5) |
C10—C11—C12—C13 | 0.6 (5) | C3—C2—C1—O2 | 1.6 (4) |
C11—C12—C13—C14 | −0.3 (5) | C7—C2—C1—O2 | −176.3 (3) |
C9—C14—C13—C12 | −0.2 (5) |
C31H33N2O7 | F(000) = 1156 |
Mr = 545.59 | Dx = 1.354 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.475 (6) Å | Cell parameters from 9926 reflections |
b = 17.669 (9) Å | θ = 2.3–30.0° |
c = 13.248 (7) Å | µ = 0.10 mm−1 |
β = 94.87 (2)° | T = 100 K |
V = 2676 (2) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.15 × 0.15 mm |
Bruker APEX-II CCD diffractometer | 6717 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.073 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0879 before and 0.0639 after correction. The Ratio of minimum to maximum transmission is 0.9174. The λ/2 correction factor is Not present. | θmax = 30.5°, θmin = 2.3° |
Tmin = 0.685, Tmax = 0.746 | h = −16→16 |
88884 measured reflections | k = −25→25 |
8099 independent reflections | l = −18→18 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.111 | H-atom parameters constrained |
wR(F2) = 0.251 | w = 1/[σ2(Fo2) + (0.0604P)2 + 5.8639P] where P = (Fo2 + 2Fc2)/3 |
S = 1.21 | (Δ/σ)max < 0.001 |
8099 reflections | Δρmax = 0.58 e Å−3 |
375 parameters | Δρmin = −0.49 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C4A | −0.0238 (4) | −0.0276 (2) | 0.1517 (2) | 0.0410 (8) | 0.53 |
C7A | 0.1540 (4) | 0.0765 (2) | 0.1393 (3) | 0.0476 (10) | 0.47 |
O4 | −0.1052 (3) | −0.0727 (2) | 0.1536 (3) | 0.0234 (7) | 0.53 |
H4 | −0.101968 | −0.104295 | 0.106542 | 0.035* | 0.53 |
O5 | 0.2215 (5) | 0.1225 (4) | 0.1361 (6) | 0.068 (2) | 0.47 |
H5 | 0.198013 | 0.154616 | 0.092240 | 0.102* | 0.47 |
C4B | −0.0238 (4) | −0.0276 (2) | 0.1517 (2) | 0.0410 (8) | 0.47 |
H4B | −0.084731 | −0.063680 | 0.155298 | 0.049* | 0.47 |
C7B | 0.1540 (4) | 0.0765 (2) | 0.1393 (3) | 0.0476 (10) | 0.53 |
H7B | 0.215742 | 0.111997 | 0.135488 | 0.057* | 0.53 |
O6 | −0.2943 (2) | 0.43895 (12) | 0.04949 (16) | 0.0300 (5) | |
O8 | 0.2916 (2) | 0.75780 (14) | 0.19018 (19) | 0.0419 (6) | |
O7 | 0.0494 (3) | 0.76615 (12) | 0.20319 (18) | 0.0428 (7) | |
H7 | 0.068856 | 0.791562 | 0.153748 | 0.064* | |
N1 | −0.1903 (2) | 0.55450 (14) | −0.04097 (17) | 0.0242 (5) | |
N2 | −0.0106 (2) | 0.65392 (13) | 0.05002 (18) | 0.0246 (5) | |
H2 | −0.040954 | 0.706427 | 0.037530 | 0.029* | |
C20 | 0.1112 (3) | 0.69656 (17) | 0.2081 (2) | 0.0346 (7) | |
H20 | 0.070377 | 0.661737 | 0.252980 | 0.041* | |
C16 | −0.0026 (3) | 0.61594 (16) | −0.0510 (2) | 0.0246 (6) | |
H16A | 0.043247 | 0.648316 | −0.094091 | 0.030* | |
H16B | 0.039228 | 0.567175 | −0.040687 | 0.030* | |
C14 | −0.2938 (3) | 0.52142 (16) | −0.0903 (2) | 0.0258 (6) | |
C8 | −0.3472 (3) | 0.37692 (19) | 0.0992 (3) | 0.0350 (7) | |
H8A | −0.350644 | 0.332461 | 0.054800 | 0.053* | |
H8B | −0.426503 | 0.391027 | 0.114064 | 0.053* | |
H8C | −0.300351 | 0.365022 | 0.162528 | 0.053* | |
C30 | 0.3874 (3) | 0.85172 (19) | 0.0542 (2) | 0.0335 (7) | |
H30 | 0.304688 | 0.848144 | 0.053492 | 0.040* | |
C21 | 0.2362 (4) | 0.70517 (18) | 0.2533 (3) | 0.0427 (9) | |
H21A | 0.237846 | 0.724603 | 0.323490 | 0.051* | |
H21B | 0.276994 | 0.655766 | 0.254514 | 0.051* | |
C13 | −0.3407 (3) | 0.54447 (18) | −0.1857 (2) | 0.0297 (6) | |
H13 | −0.304762 | 0.584788 | −0.219014 | 0.036* | |
C17 | −0.0937 (3) | 0.61262 (16) | 0.1118 (2) | 0.0267 (6) | |
H17A | −0.107603 | 0.643203 | 0.172238 | 0.032* | |
H17B | −0.058058 | 0.564056 | 0.135448 | 0.032* | |
C24 | 0.6047 (5) | 0.7369 (2) | 0.2764 (4) | 0.0634 (14) | |
H24 | 0.653547 | 0.714092 | 0.329428 | 0.076* | |
C19 | 0.1092 (3) | 0.65934 (16) | 0.1034 (2) | 0.0281 (6) | |
H19A | 0.159694 | 0.688872 | 0.060948 | 0.034* | |
H19B | 0.142643 | 0.607817 | 0.111310 | 0.034* | |
C25 | 0.6545 (4) | 0.7751 (2) | 0.2017 (4) | 0.0553 (12) | |
H25 | 0.737157 | 0.775687 | 0.200814 | 0.066* | |
C28 | 0.5588 (3) | 0.9020 (2) | −0.0159 (3) | 0.0400 (8) | |
H28 | 0.592136 | 0.933763 | −0.063673 | 0.048* | |
C27 | 0.6302 (3) | 0.8601 (2) | 0.0516 (3) | 0.0430 (9) | |
H27 | 0.712578 | 0.862353 | 0.048660 | 0.052* | |
C31 | 0.4586 (3) | 0.80939 (17) | 0.1258 (2) | 0.0334 (7) | |
C26 | 0.5835 (3) | 0.81420 (19) | 0.1246 (3) | 0.0385 (8) | |
C12 | −0.4403 (3) | 0.50905 (19) | −0.2337 (2) | 0.0326 (7) | |
H12 | −0.471430 | 0.525230 | −0.298832 | 0.039* | |
C10 | −0.4465 (3) | 0.42612 (18) | −0.0898 (3) | 0.0313 (6) | |
H10 | −0.482708 | 0.385623 | −0.057187 | 0.038* | |
C29 | 0.4357 (3) | 0.8979 (2) | −0.0142 (2) | 0.0391 (8) | |
H29 | 0.386630 | 0.927162 | −0.060458 | 0.047* | |
C9 | −0.3479 (3) | 0.46072 (17) | −0.0423 (2) | 0.0271 (6) | |
C18 | −0.2095 (3) | 0.59708 (17) | 0.0517 (2) | 0.0283 (6) | |
H18A | −0.260598 | 0.567536 | 0.093651 | 0.034* | |
H18B | −0.249120 | 0.645544 | 0.033462 | 0.034* | |
C15 | −0.1215 (3) | 0.60175 (17) | −0.1045 (2) | 0.0278 (6) | |
H15A | −0.162101 | 0.650522 | −0.118740 | 0.033* | |
H15B | −0.113195 | 0.575999 | −0.169910 | 0.033* | |
C22 | 0.4114 (4) | 0.76368 (17) | 0.2004 (3) | 0.0390 (8) | |
C11 | −0.4925 (3) | 0.4503 (2) | −0.1849 (3) | 0.0342 (7) | |
H11 | −0.560243 | 0.426458 | −0.216549 | 0.041* | |
C23 | 0.4823 (4) | 0.7304 (2) | 0.2768 (4) | 0.0550 (11) | |
H23 | 0.449127 | 0.703347 | 0.329269 | 0.066* | |
O2 | −0.0840 (3) | 0.17699 (15) | −0.0058 (2) | 0.0490 (7) | |
O3 | −0.1579 (3) | 0.05479 (18) | 0.0635 (2) | 0.0547 (8) | |
H3 | −0.162335 | 0.097787 | 0.036380 | 0.082* | |
O1 | 0.1004 (3) | 0.21320 (15) | 0.0296 (2) | 0.0510 (8) | |
C1 | 0.0181 (5) | 0.1662 (2) | 0.0357 (3) | 0.0503 (12) | |
C6 | 0.1770 (4) | 0.0082 (2) | 0.1893 (3) | 0.0417 (9) | |
H6 | 0.253215 | −0.002826 | 0.219354 | 0.050* | 0.47 |
C5 | 0.0861 (4) | −0.04385 (19) | 0.1945 (2) | 0.0403 (9) | |
H5A | 0.100740 | −0.090889 | 0.227912 | 0.048* | 0.53 |
C3 | −0.0475 (4) | 0.0422 (2) | 0.1023 (2) | 0.0439 (10) | |
C2 | 0.0426 (4) | 0.09453 (19) | 0.0946 (2) | 0.0425 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C4A | 0.072 (3) | 0.0326 (17) | 0.0187 (14) | 0.0096 (17) | 0.0040 (15) | −0.0003 (12) |
C7A | 0.088 (3) | 0.0311 (17) | 0.0247 (15) | 0.0197 (19) | 0.0076 (17) | 0.0017 (13) |
O4 | 0.0275 (19) | 0.0212 (17) | 0.0212 (17) | −0.0096 (14) | 0.0006 (14) | 0.0016 (14) |
O5 | 0.040 (3) | 0.059 (4) | 0.104 (6) | −0.022 (3) | 0.000 (3) | 0.047 (4) |
C4B | 0.072 (3) | 0.0326 (17) | 0.0187 (14) | 0.0096 (17) | 0.0040 (15) | −0.0003 (12) |
C7B | 0.088 (3) | 0.0311 (17) | 0.0247 (15) | 0.0197 (19) | 0.0076 (17) | 0.0017 (13) |
O6 | 0.0358 (12) | 0.0285 (11) | 0.0256 (10) | −0.0059 (9) | 0.0019 (9) | 0.0067 (8) |
O8 | 0.0615 (17) | 0.0284 (12) | 0.0342 (12) | −0.0165 (11) | −0.0051 (11) | 0.0072 (10) |
O7 | 0.085 (2) | 0.0173 (10) | 0.0285 (12) | −0.0048 (11) | 0.0164 (12) | −0.0014 (8) |
N1 | 0.0312 (12) | 0.0233 (11) | 0.0187 (10) | 0.0006 (9) | 0.0054 (9) | 0.0013 (9) |
N2 | 0.0378 (13) | 0.0147 (10) | 0.0221 (11) | −0.0020 (9) | 0.0081 (10) | −0.0009 (8) |
C20 | 0.064 (2) | 0.0168 (12) | 0.0239 (14) | −0.0106 (13) | 0.0071 (14) | 0.0019 (10) |
C16 | 0.0366 (15) | 0.0202 (12) | 0.0181 (12) | −0.0003 (11) | 0.0091 (11) | −0.0023 (9) |
C14 | 0.0312 (14) | 0.0232 (13) | 0.0236 (13) | 0.0038 (11) | 0.0056 (11) | 0.0000 (10) |
C8 | 0.0463 (19) | 0.0302 (15) | 0.0292 (15) | −0.0071 (14) | 0.0064 (13) | 0.0083 (12) |
C30 | 0.0401 (17) | 0.0355 (16) | 0.0240 (14) | −0.0085 (13) | −0.0014 (12) | −0.0044 (12) |
C21 | 0.077 (3) | 0.0222 (14) | 0.0273 (15) | −0.0164 (16) | −0.0065 (16) | 0.0040 (12) |
C13 | 0.0377 (16) | 0.0267 (14) | 0.0251 (14) | 0.0034 (12) | 0.0051 (12) | 0.0020 (11) |
C17 | 0.0422 (17) | 0.0185 (12) | 0.0208 (12) | −0.0040 (11) | 0.0113 (11) | −0.0006 (10) |
C24 | 0.073 (3) | 0.0276 (18) | 0.085 (3) | 0.0101 (19) | −0.021 (3) | 0.013 (2) |
C19 | 0.0417 (17) | 0.0159 (12) | 0.0270 (14) | −0.0041 (11) | 0.0046 (12) | −0.0002 (10) |
C25 | 0.059 (3) | 0.0267 (17) | 0.077 (3) | 0.0090 (17) | −0.017 (2) | −0.0080 (19) |
C28 | 0.0412 (19) | 0.052 (2) | 0.0272 (15) | −0.0072 (16) | 0.0040 (14) | −0.0064 (14) |
C27 | 0.0404 (19) | 0.047 (2) | 0.0421 (19) | −0.0038 (16) | 0.0042 (15) | −0.0218 (16) |
C31 | 0.0482 (19) | 0.0203 (13) | 0.0304 (15) | −0.0035 (12) | −0.0046 (13) | −0.0105 (11) |
C26 | 0.0439 (19) | 0.0268 (15) | 0.0423 (19) | 0.0024 (13) | −0.0102 (15) | −0.0167 (14) |
C12 | 0.0350 (16) | 0.0348 (16) | 0.0270 (14) | 0.0090 (13) | −0.0025 (12) | −0.0018 (12) |
C10 | 0.0305 (15) | 0.0290 (15) | 0.0348 (16) | −0.0011 (12) | 0.0055 (12) | 0.0014 (12) |
C29 | 0.0394 (18) | 0.053 (2) | 0.0241 (14) | −0.0083 (16) | 0.0004 (13) | 0.0019 (14) |
C9 | 0.0306 (15) | 0.0267 (14) | 0.0246 (13) | 0.0028 (11) | 0.0058 (11) | 0.0001 (11) |
C18 | 0.0374 (16) | 0.0236 (13) | 0.0254 (13) | 0.0010 (12) | 0.0120 (12) | 0.0001 (11) |
C15 | 0.0372 (16) | 0.0266 (14) | 0.0206 (12) | 0.0020 (12) | 0.0078 (11) | 0.0038 (10) |
C22 | 0.060 (2) | 0.0165 (13) | 0.0379 (17) | −0.0058 (13) | −0.0085 (16) | −0.0013 (12) |
C11 | 0.0329 (16) | 0.0361 (17) | 0.0331 (16) | 0.0039 (13) | −0.0008 (13) | −0.0040 (13) |
C23 | 0.078 (3) | 0.0233 (16) | 0.060 (3) | −0.0055 (18) | −0.013 (2) | 0.0099 (16) |
O2 | 0.078 (2) | 0.0338 (13) | 0.0380 (14) | 0.0216 (13) | 0.0186 (13) | 0.0149 (11) |
O3 | 0.069 (2) | 0.0587 (19) | 0.0376 (14) | 0.0212 (15) | 0.0093 (13) | 0.0214 (13) |
O1 | 0.086 (2) | 0.0250 (12) | 0.0435 (15) | 0.0168 (13) | 0.0168 (14) | 0.0083 (11) |
C1 | 0.097 (3) | 0.0340 (18) | 0.0225 (15) | 0.036 (2) | 0.0190 (18) | 0.0056 (13) |
C6 | 0.071 (3) | 0.0290 (16) | 0.0253 (15) | 0.0141 (16) | 0.0051 (15) | 0.0021 (12) |
C5 | 0.078 (3) | 0.0251 (15) | 0.0170 (13) | 0.0171 (16) | 0.0011 (14) | 0.0001 (11) |
C3 | 0.073 (3) | 0.0425 (19) | 0.0166 (13) | 0.0287 (19) | 0.0091 (15) | 0.0049 (13) |
C2 | 0.084 (3) | 0.0248 (15) | 0.0207 (14) | 0.0215 (17) | 0.0165 (16) | 0.0041 (11) |
C4A—O4 | 1.230 (5) | C21—H21B | 0.9900 |
C4A—C5 | 1.368 (6) | C13—C12 | 1.407 (5) |
C4A—C3 | 1.412 (5) | C13—H13 | 0.9500 |
C7A—O5 | 1.125 (7) | C17—C18 | 1.515 (5) |
C7A—C6 | 1.391 (5) | C17—H17A | 0.9900 |
C7A—C2 | 1.399 (6) | C17—H17B | 0.9900 |
O4—H4 | 0.8400 | C24—C25 | 1.363 (7) |
O5—H5 | 0.8400 | C24—C23 | 1.409 (7) |
C4B—C5 | 1.368 (6) | C24—H24 | 0.9500 |
C4B—C3 | 1.412 (5) | C19—H19A | 0.9900 |
C4B—H4B | 0.9500 | C19—H19B | 0.9900 |
C7B—C6 | 1.391 (5) | C25—C26 | 1.430 (6) |
C7B—C2 | 1.399 (6) | C25—H25 | 0.9500 |
C7B—H7B | 0.9500 | C28—C27 | 1.376 (6) |
O6—C9 | 1.370 (4) | C28—C29 | 1.416 (5) |
O6—C8 | 1.439 (4) | C28—H28 | 0.9500 |
O8—C22 | 1.374 (5) | C27—C26 | 1.404 (6) |
O8—C21 | 1.435 (4) | C27—H27 | 0.9500 |
O7—C20 | 1.419 (4) | C31—C22 | 1.419 (5) |
O7—H7 | 0.8400 | C31—C26 | 1.437 (5) |
N1—C14 | 1.431 (4) | C12—C11 | 1.385 (5) |
N1—C15 | 1.464 (4) | C12—H12 | 0.9500 |
N1—C18 | 1.473 (4) | C10—C9 | 1.389 (4) |
N2—C19 | 1.494 (4) | C10—C11 | 1.391 (5) |
N2—C17 | 1.499 (4) | C10—H10 | 0.9500 |
N2—C16 | 1.507 (3) | C29—H29 | 0.9500 |
N2—H2 | 1.0000 | C18—H18A | 0.9900 |
C20—C21 | 1.514 (5) | C18—H18B | 0.9900 |
C20—C19 | 1.532 (4) | C15—H15A | 0.9900 |
C20—H20 | 1.0000 | C15—H15B | 0.9900 |
C16—C15 | 1.504 (4) | C22—C23 | 1.376 (5) |
C16—H16A | 0.9900 | C11—H11 | 0.9500 |
C16—H16B | 0.9900 | C23—H23 | 0.9500 |
C14—C13 | 1.392 (4) | O2—C1 | 1.265 (6) |
C14—C9 | 1.417 (4) | O3—C3 | 1.345 (5) |
C8—H8A | 0.9800 | O3—H3 | 0.8400 |
C8—H8B | 0.9800 | O1—C1 | 1.265 (6) |
C8—H8C | 0.9800 | C1—C2 | 1.501 (5) |
C30—C29 | 1.371 (5) | C6—C5 | 1.397 (6) |
C30—C31 | 1.412 (5) | C6—H6 | 0.9500 |
C30—H30 | 0.9500 | C5—H5A | 0.9500 |
C21—H21A | 0.9900 | C3—C2 | 1.397 (6) |
O4—C4A—C5 | 122.1 (4) | C20—C19—H19B | 108.9 |
O4—C4A—C3 | 117.3 (4) | H19A—C19—H19B | 107.7 |
C5—C4A—C3 | 120.6 (4) | C24—C25—C26 | 120.7 (4) |
O5—C7A—C6 | 122.8 (5) | C24—C25—H25 | 119.7 |
O5—C7A—C2 | 115.3 (5) | C26—C25—H25 | 119.7 |
C6—C7A—C2 | 121.9 (4) | C27—C28—C29 | 120.1 (4) |
C4A—O4—H4 | 109.5 | C27—C28—H28 | 120.0 |
C7A—O5—H5 | 109.5 | C29—C28—H28 | 120.0 |
C5—C4B—C3 | 120.6 (4) | C28—C27—C26 | 121.2 (4) |
C5—C4B—H4B | 119.7 | C28—C27—H27 | 119.4 |
C3—C4B—H4B | 119.7 | C26—C27—H27 | 119.4 |
C6—C7B—C2 | 121.9 (4) | C30—C31—C22 | 122.4 (3) |
C6—C7B—H7B | 119.1 | C30—C31—C26 | 118.8 (3) |
C2—C7B—H7B | 119.1 | C22—C31—C26 | 118.8 (3) |
C9—O6—C8 | 116.4 (2) | C27—C26—C25 | 123.0 (4) |
C22—O8—C21 | 118.8 (3) | C27—C26—C31 | 118.8 (3) |
C20—O7—H7 | 109.5 | C25—C26—C31 | 118.1 (4) |
C14—N1—C15 | 115.9 (2) | C11—C12—C13 | 119.3 (3) |
C14—N1—C18 | 114.4 (2) | C11—C12—H12 | 120.3 |
C15—N1—C18 | 108.3 (2) | C13—C12—H12 | 120.3 |
C19—N2—C17 | 112.0 (2) | C9—C10—C11 | 120.5 (3) |
C19—N2—C16 | 109.1 (2) | C9—C10—H10 | 119.8 |
C17—N2—C16 | 111.0 (2) | C11—C10—H10 | 119.8 |
C19—N2—H2 | 108.2 | C30—C29—C28 | 120.1 (3) |
C17—N2—H2 | 108.2 | C30—C29—H29 | 120.0 |
C16—N2—H2 | 108.2 | C28—C29—H29 | 120.0 |
O7—C20—C21 | 112.6 (3) | O6—C9—C10 | 124.5 (3) |
O7—C20—C19 | 111.2 (3) | O6—C9—C14 | 115.5 (3) |
C21—C20—C19 | 110.0 (3) | C10—C9—C14 | 120.1 (3) |
O7—C20—H20 | 107.6 | N1—C18—C17 | 110.1 (2) |
C21—C20—H20 | 107.6 | N1—C18—H18A | 109.6 |
C19—C20—H20 | 107.6 | C17—C18—H18A | 109.6 |
C15—C16—N2 | 111.8 (2) | N1—C18—H18B | 109.6 |
C15—C16—H16A | 109.3 | C17—C18—H18B | 109.6 |
N2—C16—H16A | 109.3 | H18A—C18—H18B | 108.1 |
C15—C16—H16B | 109.3 | N1—C15—C16 | 109.6 (2) |
N2—C16—H16B | 109.3 | N1—C15—H15A | 109.7 |
H16A—C16—H16B | 107.9 | C16—C15—H15A | 109.7 |
C13—C14—C9 | 118.6 (3) | N1—C15—H15B | 109.7 |
C13—C14—N1 | 122.5 (3) | C16—C15—H15B | 109.7 |
C9—C14—N1 | 118.9 (3) | H15A—C15—H15B | 108.2 |
O6—C8—H8A | 109.5 | O8—C22—C23 | 124.3 (4) |
O6—C8—H8B | 109.5 | O8—C22—C31 | 114.4 (3) |
H8A—C8—H8B | 109.5 | C23—C22—C31 | 121.3 (4) |
O6—C8—H8C | 109.5 | C12—C11—C10 | 120.4 (3) |
H8A—C8—H8C | 109.5 | C12—C11—H11 | 119.8 |
H8B—C8—H8C | 109.5 | C10—C11—H11 | 119.8 |
C29—C30—C31 | 121.0 (3) | C22—C23—C24 | 119.4 (4) |
C29—C30—H30 | 119.5 | C22—C23—H23 | 120.3 |
C31—C30—H30 | 119.5 | C24—C23—H23 | 120.3 |
O8—C21—C20 | 106.6 (3) | C3—O3—H3 | 109.5 |
O8—C21—H21A | 110.4 | O1—C1—O2 | 122.8 (3) |
C20—C21—H21A | 110.4 | O1—C1—C2 | 118.6 (4) |
O8—C21—H21B | 110.4 | O2—C1—C2 | 118.6 (4) |
C20—C21—H21B | 110.4 | C7B—C6—C5 | 118.9 (4) |
H21A—C21—H21B | 108.6 | C7A—C6—C5 | 118.9 (4) |
C14—C13—C12 | 121.1 (3) | C7A—C6—H6 | 120.6 |
C14—C13—H13 | 119.5 | C5—C6—H6 | 120.6 |
C12—C13—H13 | 119.5 | C4B—C5—C6 | 120.5 (3) |
N2—C17—C18 | 111.8 (2) | C4A—C5—C6 | 120.5 (3) |
N2—C17—H17A | 109.2 | C4A—C5—H5A | 119.8 |
C18—C17—H17A | 109.2 | C6—C5—H5A | 119.8 |
N2—C17—H17B | 109.2 | O3—C3—C2 | 122.8 (3) |
C18—C17—H17B | 109.2 | O3—C3—C4B | 117.4 (4) |
H17A—C17—H17B | 107.9 | C2—C3—C4B | 119.8 (4) |
C25—C24—C23 | 121.4 (4) | O3—C3—C4A | 117.4 (4) |
C25—C24—H24 | 119.3 | C2—C3—C4A | 119.8 (4) |
C23—C24—H24 | 119.3 | C3—C2—C7A | 118.3 (3) |
N2—C19—C20 | 113.5 (3) | C3—C2—C7B | 118.3 (3) |
N2—C19—H19A | 108.9 | C3—C2—C1 | 119.2 (4) |
C20—C19—H19A | 108.9 | C7A—C2—C1 | 122.4 (4) |
N2—C19—H19B | 108.9 | C7B—C2—C1 | 122.4 (4) |
C19—N2—C16—C15 | 174.4 (2) | N2—C16—C15—N1 | −58.4 (3) |
C17—N2—C16—C15 | 50.5 (3) | C21—O8—C22—C23 | −9.6 (5) |
C15—N1—C14—C13 | −13.1 (4) | C21—O8—C22—C31 | 171.9 (3) |
C18—N1—C14—C13 | 114.0 (3) | C30—C31—C22—O8 | 6.6 (4) |
C15—N1—C14—C9 | 164.0 (3) | C26—C31—C22—O8 | −174.9 (3) |
C18—N1—C14—C9 | −68.8 (3) | C30—C31—C22—C23 | −171.9 (3) |
C22—O8—C21—C20 | −166.0 (3) | C26—C31—C22—C23 | 6.5 (5) |
O7—C20—C21—O8 | −59.2 (4) | C13—C12—C11—C10 | −0.6 (5) |
C19—C20—C21—O8 | 65.5 (3) | C9—C10—C11—C12 | 0.3 (5) |
C9—C14—C13—C12 | 0.6 (4) | O8—C22—C23—C24 | 176.5 (4) |
N1—C14—C13—C12 | 177.8 (3) | C31—C22—C23—C24 | −5.1 (6) |
C19—N2—C17—C18 | −171.6 (2) | C25—C24—C23—C22 | −0.3 (7) |
C16—N2—C17—C18 | −49.4 (3) | C2—C7B—C6—C5 | 0.2 (5) |
C17—N2—C19—C20 | −56.2 (3) | O5—C7A—C6—C5 | 176.4 (7) |
C16—N2—C19—C20 | −179.4 (2) | C2—C7A—C6—C5 | 0.2 (5) |
O7—C20—C19—N2 | −50.3 (3) | C3—C4B—C5—C6 | −0.5 (5) |
C21—C20—C19—N2 | −175.7 (2) | O4—C4A—C5—C6 | 178.9 (3) |
C23—C24—C25—C26 | 4.2 (7) | C3—C4A—C5—C6 | −0.5 (5) |
C29—C28—C27—C26 | −1.6 (5) | C7B—C6—C5—C4B | −0.5 (5) |
C29—C30—C31—C22 | 177.2 (3) | C7A—C6—C5—C4A | −0.5 (5) |
C29—C30—C31—C26 | −1.3 (5) | C5—C4B—C3—O3 | −179.0 (3) |
C28—C27—C26—C25 | −174.3 (3) | C5—C4B—C3—C2 | 1.7 (5) |
C28—C27—C26—C31 | 2.1 (5) | O4—C4A—C3—O3 | 1.6 (5) |
C24—C25—C26—C27 | 173.9 (4) | C5—C4A—C3—O3 | −179.0 (3) |
C24—C25—C26—C31 | −2.6 (5) | O4—C4A—C3—C2 | −177.7 (3) |
C30—C31—C26—C27 | −0.7 (4) | C5—C4A—C3—C2 | 1.7 (5) |
C22—C31—C26—C27 | −179.2 (3) | O3—C3—C2—C7A | 178.8 (3) |
C30—C31—C26—C25 | 175.9 (3) | C4A—C3—C2—C7A | −1.9 (5) |
C22—C31—C26—C25 | −2.6 (4) | O3—C3—C2—C7B | 178.8 (3) |
C14—C13—C12—C11 | 0.1 (5) | C4B—C3—C2—C7B | −1.9 (5) |
C31—C30—C29—C28 | 1.9 (5) | O3—C3—C2—C1 | −3.5 (5) |
C27—C28—C29—C30 | −0.5 (5) | C4B—C3—C2—C1 | 175.7 (3) |
C8—O6—C9—C10 | −1.4 (4) | C4A—C3—C2—C1 | 175.7 (3) |
C8—O6—C9—C14 | −179.5 (3) | O5—C7A—C2—C3 | −175.4 (6) |
C11—C10—C9—O6 | −177.6 (3) | C6—C7A—C2—C3 | 1.0 (5) |
C11—C10—C9—C14 | 0.3 (5) | O5—C7A—C2—C1 | 7.0 (7) |
C13—C14—C9—O6 | 177.3 (3) | C6—C7A—C2—C1 | −176.6 (3) |
N1—C14—C9—O6 | 0.0 (4) | C6—C7B—C2—C3 | 1.0 (5) |
C13—C14—C9—C10 | −0.8 (4) | C6—C7B—C2—C1 | −176.6 (3) |
N1—C14—C9—C10 | −178.1 (3) | O1—C1—C2—C3 | 179.7 (3) |
C14—N1—C18—C17 | 165.8 (2) | O2—C1—C2—C3 | −0.2 (5) |
C15—N1—C18—C17 | −63.2 (3) | O1—C1—C2—C7A | −2.7 (5) |
N2—C17—C18—N1 | 56.4 (3) | O2—C1—C2—C7A | 177.3 (3) |
C14—N1—C15—C16 | −165.7 (2) | O1—C1—C2—C7B | −2.7 (5) |
C18—N1—C15—C16 | 64.1 (3) | O2—C1—C2—C7B | 177.3 (3) |
C31H34.12N2O6.33 | F(000) = 1139 |
Mr = 536.00 | Dx = 1.322 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.296 (2) Å | Cell parameters from 9968 reflections |
b = 17.807 (4) Å | θ = 2.8–26.4° |
c = 13.459 (3) Å | µ = 0.09 mm−1 |
β = 95.99 (3)° | T = 297 K |
V = 2692.6 (10) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.1 × 0.1 mm |
Bruker APEX-II CCD diffractometer | Rint = 0.039 |
φ and ω scans | θmax = 26.3°, θmin = 2.5° |
62700 measured reflections | h = −14→14 |
5404 independent reflections | k = −22→22 |
4670 reflections with I > 2σ(I) | l = −16→16 |
Refinement on F2 | 0 restraints |
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) = 0.138 | w = 1/[σ2(Fo2) + (0.0703P)2 + 0.7038P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
5404 reflections | Δρmax = 0.22 e Å−3 |
431 parameters | Δρmin = −0.26 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C3A | 0.54852 (15) | 0.04675 (10) | 0.39582 (12) | 0.0475 (4) | 0.88 |
C4A | 0.52220 (18) | −0.02131 (10) | 0.34541 (13) | 0.0549 (4) | 0.55 |
H4A | 0.582812 | −0.055542 | 0.337940 | 0.066* | 0.55 |
O3 | 0.66097 (13) | 0.06030 (10) | 0.42938 (13) | 0.0687 (4) | 0.88 |
C3B | 0.54852 (15) | 0.04675 (10) | 0.39582 (12) | 0.0475 (4) | 0.12 |
H3B | 0.626440 | 0.057925 | 0.420702 | 0.057* | 0.12 |
C4B | 0.52220 (18) | −0.02131 (10) | 0.34541 (13) | 0.0549 (4) | 0.45 |
O4 | 0.6109 (3) | −0.0687 (2) | 0.3404 (3) | 0.0779 (10) | 0.45 |
H4 | 0.667393 | −0.055925 | 0.380012 | 0.117* | 0.45 |
O5 | 0.20363 (11) | 0.55759 (7) | 0.55002 (9) | 0.0546 (3) | |
O7 | 0.80010 (11) | 0.23984 (7) | 0.69616 (10) | 0.0598 (3) | |
O1 | 0.40044 (12) | 0.21380 (7) | 0.47572 (11) | 0.0631 (4) | |
N2 | 0.49280 (11) | 0.34455 (6) | 0.55514 (9) | 0.0384 (3) | |
H2 | 0.462254 | 0.293723 | 0.541054 | 0.046* | |
O6 | 0.55395 (13) | 0.23049 (7) | 0.70452 (11) | 0.0617 (3) | |
O2 | 0.58862 (12) | 0.17939 (8) | 0.50480 (12) | 0.0726 (4) | |
N1 | 0.31123 (11) | 0.44358 (7) | 0.46217 (9) | 0.0406 (3) | |
C17 | 0.40672 (15) | 0.38504 (10) | 0.61380 (12) | 0.0441 (4) | |
H17A | 0.441800 | 0.432143 | 0.638171 | 0.053 (5) | |
H17B | 0.391847 | 0.354904 | 0.671234 | 0.056 (5) | |
C19 | 0.61382 (14) | 0.33807 (9) | 0.61093 (13) | 0.0451 (4) | |
H19A | 0.647037 | 0.388058 | 0.621025 | 0.054* | |
H19B | 0.664697 | 0.310378 | 0.570143 | 0.045 (4) | |
C9 | 0.15254 (14) | 0.53749 (9) | 0.45707 (12) | 0.0438 (3) | |
C1 | 0.48303 (15) | 0.16857 (9) | 0.46651 (13) | 0.0491 (4) | |
C16 | 0.50322 (14) | 0.38314 (9) | 0.45727 (12) | 0.0447 (4) | |
H16A | 0.549729 | 0.352044 | 0.416688 | 0.054* | |
H16B | 0.545001 | 0.430366 | 0.469485 | 0.054* | |
C31 | 0.96804 (14) | 0.19107 (9) | 0.63045 (13) | 0.0471 (4) | |
C2 | 0.45730 (14) | 0.09732 (8) | 0.40830 (11) | 0.0423 (3) | |
C14 | 0.20754 (13) | 0.47758 (8) | 0.41083 (12) | 0.0417 (3) | |
C18 | 0.29036 (14) | 0.40067 (9) | 0.55187 (12) | 0.0449 (4) | |
H18A | 0.251255 | 0.353628 | 0.532468 | 0.054* | |
H18B | 0.238517 | 0.428962 | 0.591147 | 0.056 (5) | |
C15 | 0.38300 (16) | 0.39802 (11) | 0.40095 (13) | 0.0474 (4) | |
H15A | 0.392870 | 0.424169 | 0.339136 | 0.067 (6) | |
H15B | 0.342899 | 0.350789 | 0.384430 | 0.053 (5) | |
C30 | 0.89400 (15) | 0.14982 (10) | 0.55882 (13) | 0.0517 (4) | |
H30 | 0.811757 | 0.153238 | 0.557998 | 0.062* | |
C7 | 0.34216 (16) | 0.07914 (10) | 0.36865 (13) | 0.0507 (4) | |
H7 | 0.280452 | 0.112566 | 0.376084 | 0.061* | |
C22 | 0.92152 (16) | 0.23494 (9) | 0.70585 (14) | 0.0513 (4) | |
C10 | 0.05451 (15) | 0.57322 (10) | 0.40730 (15) | 0.0552 (4) | |
H10 | 0.017814 | 0.612293 | 0.438191 | 0.066* | |
C13 | 0.16191 (17) | 0.45685 (10) | 0.31509 (14) | 0.0532 (4) | |
H13 | 0.197289 | 0.417555 | 0.283561 | 0.071 (6) | |
C26 | 1.09432 (15) | 0.18657 (10) | 0.62891 (14) | 0.0541 (4) | |
C20 | 0.61606 (16) | 0.29944 (9) | 0.71186 (13) | 0.0496 (4) | |
H20 | 0.575141 | 0.332383 | 0.755542 | 0.059* | |
C23 | 0.9957 (2) | 0.26709 (11) | 0.78065 (18) | 0.0656 (6) | |
H23 | 0.964513 | 0.292804 | 0.832150 | 0.073 (7) | |
C21 | 0.74363 (19) | 0.29114 (11) | 0.75802 (15) | 0.0593 (5) | |
H21A | 0.783802 | 0.339349 | 0.760361 | 0.078 (7) | |
H21B | 0.745789 | 0.271725 | 0.825526 | 0.094* | |
C6 | 0.31781 (17) | 0.01219 (10) | 0.31836 (14) | 0.0578 (4) | |
H6A | 0.240421 | 0.000902 | 0.292118 | 0.069* | |
C5 | 0.40859 (19) | −0.03747 (10) | 0.30742 (13) | 0.0577 (5) | |
H5A | 0.392318 | −0.082524 | 0.273777 | 0.069* | 0.55 |
H5B | 0.392318 | −0.082524 | 0.273777 | 0.069* | 0.45 |
C25 | 1.16864 (17) | 0.22417 (11) | 0.70467 (18) | 0.0672 (6) | |
H25 | 1.250774 | 0.223629 | 0.703294 | 0.081* | |
C11 | 0.01085 (17) | 0.55083 (11) | 0.31131 (16) | 0.0617 (5) | |
H11 | −0.055021 | 0.574962 | 0.278482 | 0.074* | |
C12 | 0.06422 (18) | 0.49357 (11) | 0.26500 (15) | 0.0623 (5) | |
H12 | 0.035539 | 0.479204 | 0.200515 | 0.075* | |
C29 | 0.94168 (17) | 0.10495 (12) | 0.49072 (14) | 0.0601 (5) | |
H29 | 0.891813 | 0.077115 | 0.445288 | 0.072* | |
C27 | 1.13927 (17) | 0.14121 (13) | 0.55495 (16) | 0.0646 (5) | |
H27 | 1.220984 | 0.139109 | 0.551388 | 0.078* | |
C24 | 1.1206 (2) | 0.26084 (11) | 0.7790 (2) | 0.0755 (7) | |
H24 | 1.170861 | 0.282488 | 0.830207 | 0.091* | |
C8 | 0.1504 (2) | 0.61803 (12) | 0.59857 (18) | 0.0695 (6) | |
H8A | 0.152325 | 0.662636 | 0.558721 | 0.104* | |
H8B | 0.193608 | 0.626556 | 0.662840 | 0.088 (8) | |
H8C | 0.069288 | 0.605624 | 0.606875 | 0.131* | |
C28 | 1.06551 (17) | 0.10074 (13) | 0.48914 (15) | 0.0659 (5) | |
H28 | 1.097274 | 0.070035 | 0.442719 | 0.079* | |
H6 | 0.579 (3) | 0.2100 (18) | 0.644 (3) | 0.116 (10)* | |
H3 | 0.656 (3) | 0.108 (2) | 0.468 (3) | 0.130 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C3A | 0.0533 (9) | 0.0506 (9) | 0.0384 (8) | 0.0052 (7) | 0.0042 (7) | −0.0015 (7) |
C4A | 0.0748 (12) | 0.0477 (9) | 0.0425 (9) | 0.0191 (8) | 0.0072 (8) | 0.0000 (7) |
O3 | 0.0492 (8) | 0.0808 (11) | 0.0739 (10) | 0.0114 (7) | −0.0044 (7) | −0.0229 (9) |
C3B | 0.0533 (9) | 0.0506 (9) | 0.0384 (8) | 0.0052 (7) | 0.0042 (7) | −0.0015 (7) |
C4B | 0.0748 (12) | 0.0477 (9) | 0.0425 (9) | 0.0191 (8) | 0.0072 (8) | 0.0000 (7) |
O4 | 0.083 (2) | 0.076 (2) | 0.072 (2) | 0.0380 (18) | −0.0057 (17) | −0.0198 (17) |
O5 | 0.0552 (7) | 0.0493 (7) | 0.0589 (7) | 0.0109 (5) | 0.0031 (5) | −0.0131 (5) |
O7 | 0.0532 (7) | 0.0593 (7) | 0.0640 (8) | 0.0138 (6) | −0.0082 (6) | −0.0190 (6) |
O1 | 0.0626 (8) | 0.0409 (6) | 0.0872 (10) | 0.0009 (5) | 0.0150 (7) | −0.0149 (6) |
N2 | 0.0436 (7) | 0.0294 (6) | 0.0429 (7) | 0.0028 (5) | 0.0083 (5) | −0.0002 (5) |
O6 | 0.0783 (9) | 0.0482 (7) | 0.0595 (8) | 0.0003 (6) | 0.0118 (7) | 0.0061 (6) |
O2 | 0.0596 (8) | 0.0642 (8) | 0.0922 (11) | −0.0032 (6) | −0.0004 (7) | −0.0303 (8) |
N1 | 0.0427 (7) | 0.0386 (6) | 0.0408 (7) | 0.0059 (5) | 0.0063 (5) | 0.0001 (5) |
C17 | 0.0531 (9) | 0.0408 (8) | 0.0398 (8) | 0.0097 (7) | 0.0116 (7) | −0.0002 (7) |
H17A | 0.059 (13) | 0.055 (14) | 0.044 (12) | 0.023 (11) | −0.002 (9) | 0.000 (10) |
H17B | 0.056 (12) | 0.071 (14) | 0.043 (12) | 0.020 (10) | 0.020 (10) | 0.017 (11) |
C19 | 0.0438 (8) | 0.0376 (8) | 0.0534 (9) | 0.0029 (6) | 0.0035 (7) | −0.0005 (7) |
H19B | 0.040 (10) | 0.050 (11) | 0.045 (11) | 0.004 (9) | 0.011 (9) | −0.008 (9) |
C9 | 0.0417 (8) | 0.0379 (7) | 0.0518 (9) | −0.0011 (6) | 0.0051 (6) | 0.0006 (6) |
C1 | 0.0573 (10) | 0.0395 (8) | 0.0524 (9) | −0.0038 (7) | 0.0144 (8) | −0.0046 (7) |
C16 | 0.0487 (8) | 0.0426 (8) | 0.0451 (8) | 0.0057 (6) | 0.0156 (7) | 0.0032 (6) |
C31 | 0.0472 (8) | 0.0406 (8) | 0.0518 (9) | 0.0025 (6) | −0.0028 (7) | 0.0103 (7) |
C2 | 0.0536 (9) | 0.0361 (7) | 0.0386 (7) | −0.0008 (6) | 0.0120 (6) | 0.0010 (6) |
C14 | 0.0417 (8) | 0.0357 (7) | 0.0475 (8) | −0.0003 (6) | 0.0044 (6) | 0.0018 (6) |
C18 | 0.0464 (8) | 0.0431 (8) | 0.0468 (9) | 0.0053 (6) | 0.0130 (7) | 0.0032 (7) |
H18B | 0.065 (13) | 0.067 (14) | 0.039 (11) | 0.021 (11) | 0.012 (10) | 0.010 (10) |
C15 | 0.0535 (10) | 0.0486 (9) | 0.0410 (8) | 0.0078 (7) | 0.0095 (7) | −0.0018 (7) |
H15A | 0.075 (14) | 0.091 (17) | 0.041 (12) | 0.035 (12) | 0.029 (11) | 0.026 (12) |
H15B | 0.041 (11) | 0.051 (13) | 0.067 (14) | 0.020 (10) | 0.010 (10) | 0.005 (11) |
C30 | 0.0426 (8) | 0.0598 (10) | 0.0517 (9) | 0.0050 (7) | −0.0004 (7) | 0.0002 (8) |
C7 | 0.0538 (9) | 0.0456 (9) | 0.0537 (9) | −0.0008 (7) | 0.0098 (7) | −0.0018 (7) |
C22 | 0.0541 (9) | 0.0375 (8) | 0.0591 (10) | 0.0045 (7) | −0.0095 (8) | 0.0026 (7) |
C10 | 0.0485 (9) | 0.0429 (9) | 0.0739 (12) | 0.0069 (7) | 0.0056 (8) | 0.0042 (8) |
C13 | 0.0589 (10) | 0.0481 (9) | 0.0511 (10) | 0.0032 (8) | −0.0017 (8) | −0.0037 (8) |
H13 | 0.077 (16) | 0.096 (19) | 0.035 (12) | 0.007 (14) | −0.018 (11) | −0.006 (12) |
C26 | 0.0464 (9) | 0.0476 (9) | 0.0665 (11) | −0.0029 (7) | −0.0027 (8) | 0.0195 (8) |
C20 | 0.0606 (10) | 0.0415 (8) | 0.0464 (9) | 0.0107 (7) | 0.0051 (7) | −0.0053 (7) |
C23 | 0.0720 (13) | 0.0435 (10) | 0.0759 (14) | 0.0045 (9) | −0.0182 (11) | −0.0089 (9) |
H23 | 0.059 (14) | 0.054 (14) | 0.10 (2) | −0.006 (12) | −0.007 (13) | 0.001 (14) |
C21 | 0.0722 (12) | 0.0502 (10) | 0.0527 (10) | 0.0174 (9) | −0.0070 (9) | −0.0121 (8) |
H21A | 0.080 (16) | 0.057 (15) | 0.093 (17) | 0.030 (13) | −0.011 (13) | −0.033 (13) |
C6 | 0.0611 (11) | 0.0522 (10) | 0.0592 (11) | −0.0073 (8) | 0.0019 (8) | −0.0043 (8) |
C5 | 0.0834 (13) | 0.0411 (8) | 0.0473 (9) | −0.0018 (8) | 0.0000 (9) | −0.0044 (7) |
C25 | 0.0506 (10) | 0.0521 (11) | 0.0950 (15) | −0.0083 (8) | −0.0107 (10) | 0.0111 (10) |
C11 | 0.0519 (10) | 0.0570 (11) | 0.0726 (12) | 0.0041 (8) | −0.0105 (9) | 0.0138 (9) |
C12 | 0.0633 (11) | 0.0643 (11) | 0.0558 (10) | 0.0003 (9) | −0.0098 (9) | 0.0042 (9) |
C29 | 0.0537 (10) | 0.0745 (12) | 0.0520 (10) | 0.0020 (9) | 0.0045 (8) | −0.0052 (9) |
C27 | 0.0448 (9) | 0.0786 (13) | 0.0718 (12) | 0.0022 (9) | 0.0129 (9) | 0.0173 (11) |
C24 | 0.0722 (13) | 0.0471 (10) | 0.0989 (17) | −0.0092 (9) | −0.0303 (12) | −0.0032 (11) |
C8 | 0.0831 (14) | 0.0574 (11) | 0.0692 (13) | 0.0163 (10) | 0.0132 (11) | −0.0192 (10) |
H8B | 0.12 (2) | 0.065 (15) | 0.071 (16) | 0.048 (14) | −0.007 (15) | −0.043 (14) |
C28 | 0.0562 (10) | 0.0857 (14) | 0.0576 (11) | 0.0079 (10) | 0.0145 (9) | 0.0017 (10) |
C3A—O3 | 1.325 (2) | C2—C7 | 1.392 (2) |
C3A—C2 | 1.392 (2) | C14—C13 | 1.387 (2) |
C3A—C4A | 1.405 (3) | C18—H18A | 0.9700 |
C4A—C5 | 1.362 (3) | C18—H18B | 0.9700 |
C4A—H4A | 0.9300 | C15—H15A | 0.9700 |
O3—H3 | 1.01 (4) | C15—H15B | 0.9700 |
C3B—C2 | 1.392 (2) | C30—C29 | 1.368 (3) |
C3B—C4B | 1.405 (3) | C30—H30 | 0.9300 |
C3B—H3B | 0.9300 | C7—C6 | 1.384 (2) |
C4B—O4 | 1.317 (3) | C7—H7 | 0.9300 |
C4B—C5 | 1.362 (3) | C22—C23 | 1.366 (3) |
O4—H4 | 0.8200 | C10—C11 | 1.392 (3) |
O5—C9 | 1.370 (2) | C10—H10 | 0.9300 |
O5—C8 | 1.425 (2) | C13—C12 | 1.394 (3) |
O7—C22 | 1.367 (2) | C13—H13 | 0.9300 |
O7—C21 | 1.430 (2) | C26—C27 | 1.417 (3) |
O1—C1 | 1.249 (2) | C26—C25 | 1.419 (3) |
N2—C19 | 1.494 (2) | C20—C21 | 1.516 (3) |
N2—C17 | 1.4998 (19) | C20—H20 | 0.9800 |
N2—C16 | 1.5012 (19) | C23—C24 | 1.418 (3) |
N2—H2 | 0.9800 | C23—H23 | 0.9300 |
O6—C20 | 1.412 (2) | C21—H21A | 0.9700 |
O6—H6 | 0.96 (3) | C21—H21B | 0.9700 |
O2—C1 | 1.264 (2) | C6—C5 | 1.374 (3) |
N1—C14 | 1.431 (2) | C6—H6A | 0.9300 |
N1—C15 | 1.461 (2) | C5—H5A | 0.9300 |
N1—C18 | 1.468 (2) | C5—H5B | 0.9300 |
C17—C18 | 1.507 (2) | C25—C24 | 1.354 (3) |
C17—H17A | 0.9700 | C25—H25 | 0.9300 |
C17—H17B | 0.9700 | C11—C12 | 1.368 (3) |
C19—C20 | 1.521 (2) | C11—H11 | 0.9300 |
C19—H19A | 0.9700 | C12—H12 | 0.9300 |
C19—H19B | 0.9700 | C29—C28 | 1.403 (3) |
C9—C10 | 1.387 (2) | C29—H29 | 0.9300 |
C9—C14 | 1.411 (2) | C27—C28 | 1.358 (3) |
C1—C2 | 1.503 (2) | C27—H27 | 0.9300 |
C16—C15 | 1.508 (2) | C24—H24 | 0.9300 |
C16—H16A | 0.9700 | C8—H8A | 0.9600 |
C16—H16B | 0.9700 | C8—H8B | 0.9600 |
C31—C30 | 1.414 (2) | C8—H8C | 0.9600 |
C31—C22 | 1.424 (3) | C28—H28 | 0.9300 |
C31—C26 | 1.431 (2) | ||
O3—C3A—C2 | 122.44 (16) | C16—C15—H15B | 109.7 |
O3—C3A—C4A | 117.94 (16) | H15A—C15—H15B | 108.2 |
C2—C3A—C4A | 119.62 (16) | C29—C30—C31 | 120.93 (16) |
C5—C4A—C3A | 120.47 (16) | C29—C30—H30 | 119.5 |
C5—C4A—H4A | 119.8 | C31—C30—H30 | 119.5 |
C3A—C4A—H4A | 119.8 | C6—C7—C2 | 121.20 (16) |
C3A—O3—H3 | 103.4 (18) | C6—C7—H7 | 119.4 |
C2—C3B—C4B | 119.62 (16) | C2—C7—H7 | 119.4 |
C2—C3B—H3B | 120.2 | C23—C22—O7 | 125.12 (18) |
C4B—C3B—H3B | 120.2 | C23—C22—C31 | 120.77 (18) |
O4—C4B—C5 | 122.5 (2) | O7—C22—C31 | 114.09 (14) |
O4—C4B—C3B | 117.0 (2) | C9—C10—C11 | 120.28 (17) |
C5—C4B—C3B | 120.47 (16) | C9—C10—H10 | 119.9 |
C4B—O4—H4 | 109.5 | C11—C10—H10 | 119.9 |
C9—O5—C8 | 117.30 (15) | C14—C13—C12 | 121.53 (18) |
C22—O7—C21 | 119.29 (14) | C14—C13—H13 | 119.2 |
C19—N2—C17 | 112.46 (12) | C12—C13—H13 | 119.2 |
C19—N2—C16 | 108.96 (12) | C27—C26—C25 | 123.05 (18) |
C17—N2—C16 | 110.88 (12) | C27—C26—C31 | 118.24 (17) |
C19—N2—H2 | 108.1 | C25—C26—C31 | 118.62 (19) |
C17—N2—H2 | 108.1 | O6—C20—C21 | 112.83 (14) |
C16—N2—H2 | 108.1 | O6—C20—C19 | 111.66 (14) |
C20—O6—H6 | 101.7 (19) | C21—C20—C19 | 109.68 (15) |
C14—N1—C15 | 115.93 (13) | O6—C20—H20 | 107.5 |
C14—N1—C18 | 115.06 (12) | C21—C20—H20 | 107.5 |
C15—N1—C18 | 108.72 (13) | C19—C20—H20 | 107.5 |
N2—C17—C18 | 111.94 (13) | C22—C23—C24 | 119.3 (2) |
N2—C17—H17A | 109.2 | C22—C23—H23 | 120.3 |
C18—C17—H17A | 109.2 | C24—C23—H23 | 120.3 |
N2—C17—H17B | 109.2 | O7—C21—C20 | 106.64 (14) |
C18—C17—H17B | 109.2 | O7—C21—H21A | 110.4 |
H17A—C17—H17B | 107.9 | C20—C21—H21A | 110.4 |
N2—C19—C20 | 114.40 (14) | O7—C21—H21B | 110.4 |
N2—C19—H19A | 108.7 | C20—C21—H21B | 110.4 |
C20—C19—H19A | 108.7 | H21A—C21—H21B | 108.6 |
N2—C19—H19B | 108.7 | C5—C6—C7 | 119.63 (18) |
C20—C19—H19B | 108.7 | C5—C6—H6A | 120.2 |
H19A—C19—H19B | 107.6 | C7—C6—H6A | 120.2 |
O5—C9—C10 | 124.07 (15) | C4B—C5—C6 | 120.56 (17) |
O5—C9—C14 | 115.94 (14) | C4A—C5—C6 | 120.56 (17) |
C10—C9—C14 | 119.98 (16) | C4A—C5—H5A | 119.7 |
O1—C1—O2 | 122.99 (16) | C6—C5—H5A | 119.7 |
O1—C1—C2 | 119.37 (16) | C4B—C5—H5B | 119.7 |
O2—C1—C2 | 117.64 (15) | C6—C5—H5B | 119.7 |
N2—C16—C15 | 111.87 (13) | C24—C25—C26 | 120.36 (19) |
N2—C16—H16A | 109.2 | C24—C25—H25 | 119.8 |
C15—C16—H16A | 109.2 | C26—C25—H25 | 119.8 |
N2—C16—H16B | 109.2 | C12—C11—C10 | 120.41 (17) |
C15—C16—H16B | 109.2 | C12—C11—H11 | 119.8 |
H16A—C16—H16B | 107.9 | C10—C11—H11 | 119.8 |
C30—C31—C22 | 122.33 (15) | C11—C12—C13 | 119.57 (18) |
C30—C31—C26 | 118.71 (17) | C11—C12—H12 | 120.2 |
C22—C31—C26 | 118.92 (16) | C13—C12—H12 | 120.2 |
C3B—C2—C7 | 118.51 (15) | C30—C29—C28 | 120.27 (19) |
C3A—C2—C7 | 118.51 (15) | C30—C29—H29 | 119.9 |
C3B—C2—C1 | 120.24 (15) | C28—C29—H29 | 119.9 |
C3A—C2—C1 | 120.24 (15) | C28—C27—C26 | 121.36 (17) |
C7—C2—C1 | 121.22 (15) | C28—C27—H27 | 119.3 |
C13—C14—C9 | 118.22 (15) | C26—C27—H27 | 119.3 |
C13—C14—N1 | 122.83 (15) | C25—C24—C23 | 121.72 (19) |
C9—C14—N1 | 118.86 (14) | C25—C24—H24 | 119.1 |
N1—C18—C17 | 110.19 (13) | C23—C24—H24 | 119.1 |
N1—C18—H18A | 109.6 | O5—C8—H8A | 109.5 |
C17—C18—H18A | 109.6 | O5—C8—H8B | 109.5 |
N1—C18—H18B | 109.6 | H8A—C8—H8B | 109.5 |
C17—C18—H18B | 109.6 | O5—C8—H8C | 109.5 |
H18A—C18—H18B | 108.1 | H8A—C8—H8C | 109.5 |
N1—C15—C16 | 109.74 (14) | H8B—C8—H8C | 109.5 |
N1—C15—H15A | 109.7 | C27—C28—C29 | 120.43 (19) |
C16—C15—H15A | 109.7 | C27—C28—H28 | 119.8 |
N1—C15—H15B | 109.7 | C29—C28—H28 | 119.8 |
C31H34N2O6.17 | F(000) = 1133 |
Mr = 533.32 | Dx = 1.338 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.20 (2) Å | Cell parameters from 9158 reflections |
b = 17.71 (3) Å | θ = 2.8–30.2° |
c = 13.40 (3) Å | µ = 0.09 mm−1 |
β = 94.85 (7)° | T = 293 K |
V = 2648 (9) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.2 × 0.15 mm |
Bruker APEX-II CCD diffractometer | 5620 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.142 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1544 before and 0.0898 after correction. The Ratio of minimum to maximum transmission is 0.7079. The λ/2 correction factor is Not present. | θmax = 30.4°, θmin = 2.3° |
Tmin = 0.528, Tmax = 0.746 | h = −15→15 |
67030 measured reflections | k = −24→25 |
7947 independent reflections | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.107 | H-atom parameters constrained |
wR(F2) = 0.207 | w = 1/[σ2(Fo2) + 9.7346P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.007 |
7947 reflections | Δρmax = 0.32 e Å−3 |
365 parameters | Δρmin = −0.37 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C3A | 0.4480 (3) | 0.04163 (18) | 0.6042 (3) | 0.0240 (7) | 0.87 |
C5A | 0.5918 (4) | −0.03970 (18) | 0.6960 (3) | 0.0281 (8) | 0.3 |
O3 | 0.3355 (3) | 0.05160 (19) | 0.5671 (3) | 0.0371 (8) | 0.87 |
H3 | 0.328637 | 0.093254 | 0.540499 | 0.056* | 0.87 |
O4 | 0.6361 (11) | −0.0971 (6) | 0.7532 (8) | 0.052 (3) | 0.3 |
H4 | 0.600612 | −0.136155 | 0.736235 | 0.077* | 0.3 |
C3B | 0.4480 (3) | 0.04163 (18) | 0.6042 (3) | 0.0240 (7) | 0.13 |
H3B | 0.370101 | 0.050761 | 0.577068 | 0.029* | 0.13 |
C5B | 0.5918 (4) | −0.03970 (18) | 0.6960 (3) | 0.0281 (8) | 0.7 |
H5B | 0.609482 | −0.084780 | 0.729655 | 0.034* | 0.7 |
O7 | 0.1979 (2) | 0.23968 (13) | 0.30618 (19) | 0.0283 (5) | |
O6 | 0.4472 (2) | 0.22878 (13) | 0.3013 (2) | 0.0321 (6) | |
H6 | 0.436374 | 0.210560 | 0.356031 | 0.048* | |
O5 | 0.8030 (2) | 0.55769 (12) | 0.45134 (18) | 0.0245 (5) | |
O2 | 0.4053 (2) | 0.17633 (14) | 0.4932 (2) | 0.0324 (6) | |
O1 | 0.5945 (2) | 0.21474 (13) | 0.5281 (2) | 0.0304 (6) | |
N1 | 0.5051 (2) | 0.34560 (14) | 0.4475 (2) | 0.0195 (5) | |
H1 | 0.534182 | 0.294324 | 0.462638 | 0.023* | |
N2 | 0.6880 (2) | 0.44505 (14) | 0.5405 (2) | 0.0200 (5) | |
C28 | −0.0733 (3) | 0.0977 (2) | 0.5132 (3) | 0.0270 (7) | |
H28 | −0.106097 | 0.066154 | 0.559249 | 0.032* | |
C29 | 0.0535 (3) | 0.10340 (19) | 0.5129 (2) | 0.0240 (7) | |
H29 | 0.103405 | 0.076252 | 0.558863 | 0.029* | |
C30 | 0.1015 (3) | 0.14927 (18) | 0.4441 (2) | 0.0207 (6) | |
H30 | 0.184287 | 0.153840 | 0.444835 | 0.025* | |
C31 | 0.0275 (3) | 0.18966 (17) | 0.3723 (2) | 0.0205 (6) | |
C22 | 0.0748 (3) | 0.23407 (17) | 0.2953 (3) | 0.0234 (7) | |
C21 | 0.2575 (3) | 0.29006 (19) | 0.2422 (3) | 0.0276 (7) | |
H21A | 0.217439 | 0.338666 | 0.237881 | 0.033* | |
H21B | 0.257515 | 0.269145 | 0.175293 | 0.033* | |
C20 | 0.3856 (3) | 0.29865 (17) | 0.2898 (3) | 0.0250 (7) | |
H20 | 0.429349 | 0.330390 | 0.245264 | 0.030* | |
C19 | 0.3846 (3) | 0.33987 (17) | 0.3904 (3) | 0.0227 (7) | |
H19A | 0.353177 | 0.390397 | 0.378237 | 0.027* | |
H19B | 0.330547 | 0.313590 | 0.431399 | 0.027* | |
C17 | 0.5950 (3) | 0.38483 (17) | 0.3882 (2) | 0.0212 (6) | |
H17A | 0.561262 | 0.432071 | 0.362213 | 0.025* | |
H17B | 0.611700 | 0.353501 | 0.331631 | 0.025* | |
C18 | 0.7116 (3) | 0.40072 (17) | 0.4521 (3) | 0.0224 (7) | |
H18A | 0.749511 | 0.353382 | 0.472871 | 0.027* | |
H18B | 0.765984 | 0.428261 | 0.412721 | 0.027* | |
C14 | 0.7924 (3) | 0.47889 (16) | 0.5930 (2) | 0.0207 (6) | |
C9 | 0.8512 (3) | 0.53818 (17) | 0.5455 (2) | 0.0208 (6) | |
C10 | 0.9505 (3) | 0.57420 (17) | 0.5967 (3) | 0.0245 (7) | |
H10 | 0.989543 | 0.612834 | 0.565508 | 0.029* | |
C11 | 0.9905 (3) | 0.55258 (19) | 0.6931 (3) | 0.0276 (7) | |
H11 | 1.056153 | 0.576773 | 0.726173 | 0.033* | |
C23 | 0.0013 (4) | 0.26580 (18) | 0.2193 (3) | 0.0297 (8) | |
H23 | 0.033937 | 0.291772 | 0.167718 | 0.036* | |
C24 | −0.1249 (4) | 0.25856 (19) | 0.2202 (3) | 0.0312 (8) | |
H24 | −0.174396 | 0.279151 | 0.167926 | 0.037* | |
C25 | −0.1753 (3) | 0.22220 (19) | 0.2958 (3) | 0.0286 (8) | |
H25 | −0.258111 | 0.221718 | 0.297680 | 0.034* | |
C26 | −0.1005 (3) | 0.18473 (17) | 0.3723 (3) | 0.0214 (6) | |
C27 | −0.1481 (3) | 0.13838 (19) | 0.4460 (3) | 0.0257 (7) | |
H27 | −0.230676 | 0.135454 | 0.448866 | 0.031* | |
C8 | 0.8613 (3) | 0.61781 (19) | 0.4018 (3) | 0.0281 (8) | |
H8A | 0.821317 | 0.625658 | 0.336400 | 0.042* | |
H8B | 0.943437 | 0.604507 | 0.395677 | 0.042* | |
H8C | 0.857951 | 0.663338 | 0.440378 | 0.042* | |
C12 | 0.9333 (3) | 0.49507 (19) | 0.7407 (3) | 0.0280 (7) | |
H12 | 0.960010 | 0.480521 | 0.805500 | 0.034* | |
C13 | 0.8347 (3) | 0.45928 (18) | 0.6898 (3) | 0.0262 (7) | |
H13 | 0.796112 | 0.420969 | 0.722071 | 0.031* | |
C15 | 0.6132 (3) | 0.40023 (18) | 0.6026 (3) | 0.0242 (7) | |
H15A | 0.601793 | 0.427162 | 0.664080 | 0.029* | |
H15B | 0.652376 | 0.352608 | 0.619919 | 0.029* | |
C16 | 0.4916 (3) | 0.38551 (17) | 0.5448 (2) | 0.0228 (7) | |
H16A | 0.442703 | 0.355022 | 0.585597 | 0.027* | |
H16B | 0.450749 | 0.433201 | 0.531467 | 0.027* | |
C4 | 0.4756 (3) | −0.02634 (18) | 0.6553 (3) | 0.0266 (7) | |
H4A | 0.416125 | −0.062229 | 0.661911 | 0.032* | 0.87 |
H4B | 0.416125 | −0.062229 | 0.661911 | 0.032* | 0.13 |
C2 | 0.5379 (3) | 0.09577 (17) | 0.5939 (2) | 0.0200 (6) | |
C1 | 0.5116 (3) | 0.16733 (18) | 0.5348 (3) | 0.0250 (7) | |
C6 | 0.6822 (3) | 0.0131 (2) | 0.6873 (3) | 0.0289 (8) | |
H6A | 0.759736 | 0.003855 | 0.715064 | 0.035* | 0.3 |
H6B | 0.759736 | 0.003855 | 0.715064 | 0.035* | 0.7 |
C7 | 0.6541 (3) | 0.08004 (19) | 0.6360 (3) | 0.0252 (7) | |
H7 | 0.714364 | 0.115418 | 0.629577 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C3A | 0.0268 (17) | 0.0219 (15) | 0.0238 (16) | −0.0023 (13) | 0.0055 (13) | 0.0023 (13) |
C5A | 0.045 (2) | 0.0166 (15) | 0.0233 (17) | 0.0034 (14) | 0.0070 (15) | 0.0025 (12) |
O3 | 0.0266 (16) | 0.0387 (18) | 0.0452 (19) | −0.0070 (13) | −0.0025 (14) | 0.0197 (15) |
O4 | 0.078 (8) | 0.034 (5) | 0.043 (6) | 0.003 (5) | 0.006 (5) | 0.011 (5) |
C3B | 0.0268 (17) | 0.0219 (15) | 0.0238 (16) | −0.0023 (13) | 0.0055 (13) | 0.0023 (13) |
C5B | 0.045 (2) | 0.0166 (15) | 0.0233 (17) | 0.0034 (14) | 0.0070 (15) | 0.0025 (12) |
O7 | 0.0290 (13) | 0.0230 (12) | 0.0336 (14) | −0.0040 (10) | 0.0069 (11) | 0.0092 (10) |
O6 | 0.0388 (15) | 0.0166 (11) | 0.0436 (16) | −0.0019 (10) | 0.0198 (13) | −0.0021 (10) |
O5 | 0.0280 (12) | 0.0165 (10) | 0.0301 (13) | −0.0052 (9) | 0.0089 (10) | 0.0052 (9) |
O2 | 0.0292 (14) | 0.0268 (13) | 0.0424 (15) | 0.0000 (11) | 0.0100 (12) | 0.0116 (11) |
O1 | 0.0286 (13) | 0.0155 (10) | 0.0487 (16) | −0.0038 (10) | 0.0125 (12) | 0.0053 (11) |
N1 | 0.0233 (14) | 0.0103 (11) | 0.0259 (14) | 0.0010 (10) | 0.0090 (11) | 0.0012 (10) |
N2 | 0.0244 (14) | 0.0140 (11) | 0.0229 (13) | −0.0022 (10) | 0.0092 (11) | 0.0011 (10) |
C28 | 0.0268 (17) | 0.0300 (17) | 0.0256 (17) | −0.0028 (14) | 0.0106 (14) | −0.0022 (14) |
C29 | 0.0243 (17) | 0.0267 (16) | 0.0209 (16) | −0.0003 (13) | 0.0022 (13) | −0.0005 (13) |
C30 | 0.0163 (14) | 0.0217 (14) | 0.0242 (16) | −0.0022 (12) | 0.0023 (12) | −0.0018 (12) |
C31 | 0.0241 (16) | 0.0139 (13) | 0.0238 (16) | −0.0023 (12) | 0.0044 (13) | −0.0058 (11) |
C22 | 0.0305 (18) | 0.0113 (13) | 0.0285 (17) | −0.0007 (12) | 0.0038 (14) | −0.0027 (12) |
C21 | 0.036 (2) | 0.0182 (15) | 0.0286 (18) | −0.0073 (14) | 0.0022 (15) | 0.0045 (13) |
C20 | 0.0326 (18) | 0.0143 (14) | 0.0296 (18) | −0.0052 (13) | 0.0119 (15) | 0.0023 (12) |
C19 | 0.0232 (16) | 0.0148 (13) | 0.0311 (17) | −0.0004 (12) | 0.0079 (14) | 0.0031 (12) |
C17 | 0.0247 (16) | 0.0154 (13) | 0.0252 (16) | −0.0028 (12) | 0.0129 (13) | −0.0007 (12) |
C18 | 0.0246 (16) | 0.0153 (13) | 0.0289 (17) | −0.0004 (12) | 0.0108 (13) | −0.0013 (12) |
C14 | 0.0235 (16) | 0.0114 (12) | 0.0288 (17) | 0.0010 (12) | 0.0114 (13) | −0.0005 (12) |
C9 | 0.0223 (15) | 0.0132 (13) | 0.0279 (16) | 0.0025 (11) | 0.0087 (13) | 0.0006 (12) |
C10 | 0.0234 (16) | 0.0130 (13) | 0.0381 (19) | −0.0011 (12) | 0.0089 (14) | −0.0015 (13) |
C11 | 0.0267 (17) | 0.0206 (15) | 0.0355 (19) | 0.0023 (13) | 0.0034 (15) | −0.0067 (14) |
C23 | 0.044 (2) | 0.0120 (14) | 0.0330 (19) | 0.0021 (14) | 0.0003 (17) | 0.0020 (13) |
C24 | 0.037 (2) | 0.0174 (15) | 0.037 (2) | 0.0065 (14) | −0.0083 (16) | 0.0000 (14) |
C25 | 0.0246 (17) | 0.0201 (15) | 0.040 (2) | 0.0039 (13) | −0.0030 (15) | −0.0082 (14) |
C26 | 0.0225 (16) | 0.0156 (13) | 0.0263 (17) | 0.0023 (12) | 0.0021 (13) | −0.0072 (12) |
C27 | 0.0189 (16) | 0.0267 (16) | 0.0320 (18) | −0.0024 (13) | 0.0057 (14) | −0.0080 (14) |
C8 | 0.0301 (18) | 0.0208 (15) | 0.0347 (19) | −0.0044 (14) | 0.0113 (15) | 0.0078 (14) |
C12 | 0.035 (2) | 0.0217 (16) | 0.0271 (18) | 0.0047 (14) | 0.0030 (15) | −0.0027 (13) |
C13 | 0.0354 (19) | 0.0151 (14) | 0.0291 (18) | 0.0018 (13) | 0.0084 (15) | 0.0011 (13) |
C15 | 0.0293 (18) | 0.0185 (14) | 0.0264 (17) | −0.0034 (13) | 0.0116 (14) | 0.0021 (13) |
C16 | 0.0253 (16) | 0.0169 (14) | 0.0286 (17) | −0.0001 (12) | 0.0169 (14) | −0.0008 (12) |
C4 | 0.038 (2) | 0.0184 (15) | 0.0242 (17) | −0.0121 (14) | 0.0078 (15) | −0.0012 (13) |
C2 | 0.0244 (16) | 0.0146 (13) | 0.0223 (15) | −0.0010 (12) | 0.0090 (13) | −0.0007 (11) |
C1 | 0.0293 (18) | 0.0169 (14) | 0.0312 (18) | 0.0001 (13) | 0.0165 (15) | 0.0007 (13) |
C6 | 0.0296 (18) | 0.0309 (18) | 0.0272 (18) | 0.0044 (15) | 0.0074 (15) | 0.0042 (14) |
C7 | 0.0247 (17) | 0.0245 (16) | 0.0273 (17) | −0.0015 (13) | 0.0073 (14) | −0.0001 (13) |
C3A—O3 | 1.326 (5) | C20—H20 | 0.9800 |
C3A—C2 | 1.406 (5) | C19—H19A | 0.9700 |
C3A—C4 | 1.407 (5) | C19—H19B | 0.9700 |
C5A—O4 | 1.343 (10) | C17—C18 | 1.526 (5) |
C5A—C4 | 1.388 (6) | C17—H17A | 0.9700 |
C5A—C6 | 1.390 (5) | C17—H17B | 0.9700 |
O3—H3 | 0.8200 | C18—H18A | 0.9700 |
O4—H4 | 0.8200 | C18—H18B | 0.9700 |
C3B—C2 | 1.406 (5) | C14—C13 | 1.387 (5) |
C3B—C4 | 1.407 (5) | C14—C9 | 1.419 (4) |
C3B—H3B | 0.9300 | C9—C10 | 1.409 (5) |
C5B—C4 | 1.388 (6) | C10—C11 | 1.385 (6) |
C5B—C6 | 1.390 (5) | C10—H10 | 0.9300 |
C5B—H5B | 0.9300 | C11—C12 | 1.387 (5) |
O7—C22 | 1.378 (5) | C11—H11 | 0.9300 |
O7—C21 | 1.440 (4) | C23—C24 | 1.421 (6) |
O6—C20 | 1.418 (4) | C23—H23 | 0.9300 |
O6—H6 | 0.8200 | C24—C25 | 1.362 (6) |
O5—C9 | 1.374 (5) | C24—H24 | 0.9300 |
O5—C8 | 1.440 (4) | C25—C26 | 1.431 (5) |
O2—C1 | 1.280 (5) | C25—H25 | 0.9300 |
O1—C1 | 1.261 (4) | C26—C27 | 1.421 (5) |
N1—C19 | 1.498 (5) | C27—H27 | 0.9300 |
N1—C16 | 1.502 (5) | C8—H8A | 0.9600 |
N1—C17 | 1.504 (4) | C8—H8B | 0.9600 |
N1—H1 | 0.9800 | C8—H8C | 0.9600 |
N2—C14 | 1.443 (5) | C12—C13 | 1.400 (5) |
N2—C15 | 1.463 (4) | C12—H12 | 0.9300 |
N2—C18 | 1.465 (5) | C13—H13 | 0.9300 |
C28—C27 | 1.381 (5) | C15—C16 | 1.530 (5) |
C28—C29 | 1.425 (5) | C15—H15A | 0.9700 |
C28—H28 | 0.9300 | C15—H15B | 0.9700 |
C29—C30 | 1.371 (5) | C16—H16A | 0.9700 |
C29—H29 | 0.9300 | C16—H16B | 0.9700 |
C30—C31 | 1.410 (5) | C4—H4A | 0.9300 |
C30—H30 | 0.9300 | C4—H4B | 0.9300 |
C31—C22 | 1.434 (5) | C2—C7 | 1.402 (5) |
C31—C26 | 1.436 (5) | C2—C1 | 1.510 (5) |
C22—C23 | 1.374 (5) | C6—C7 | 1.393 (5) |
C21—C20 | 1.528 (6) | C6—H6A | 0.9300 |
C21—H21A | 0.9700 | C6—H6B | 0.9300 |
C21—H21B | 0.9700 | C7—H7 | 0.9300 |
C20—C19 | 1.534 (5) | ||
O3—C3A—C2 | 122.6 (3) | C9—C14—N2 | 118.5 (3) |
O3—C3A—C4 | 117.3 (3) | O5—C9—C10 | 124.5 (3) |
C2—C3A—C4 | 120.1 (3) | O5—C9—C14 | 115.9 (3) |
O4—C5A—C4 | 129.9 (6) | C10—C9—C14 | 119.6 (3) |
O4—C5A—C6 | 108.7 (6) | C11—C10—C9 | 120.6 (3) |
C4—C5A—C6 | 121.2 (3) | C11—C10—H10 | 119.7 |
C3A—O3—H3 | 109.5 | C9—C10—H10 | 119.7 |
C5A—O4—H4 | 109.5 | C10—C11—C12 | 120.4 (3) |
C2—C3B—C4 | 120.1 (3) | C10—C11—H11 | 119.8 |
C2—C3B—H3B | 119.9 | C12—C11—H11 | 119.8 |
C4—C3B—H3B | 119.9 | C22—C23—C24 | 119.4 (4) |
C4—C5B—C6 | 121.2 (3) | C22—C23—H23 | 120.3 |
C4—C5B—H5B | 119.4 | C24—C23—H23 | 120.3 |
C6—C5B—H5B | 119.4 | C25—C24—C23 | 121.6 (4) |
C22—O7—C21 | 119.5 (3) | C25—C24—H24 | 119.2 |
C20—O6—H6 | 109.5 | C23—C24—H24 | 119.2 |
C9—O5—C8 | 116.8 (3) | C24—C25—C26 | 119.9 (4) |
C19—N1—C16 | 108.8 (3) | C24—C25—H25 | 120.1 |
C19—N1—C17 | 112.1 (3) | C26—C25—H25 | 120.1 |
C16—N1—C17 | 111.2 (3) | C27—C26—C25 | 122.3 (3) |
C19—N1—H1 | 108.2 | C27—C26—C31 | 117.9 (3) |
C16—N1—H1 | 108.2 | C25—C26—C31 | 119.7 (3) |
C17—N1—H1 | 108.2 | C28—C27—C26 | 120.8 (3) |
C14—N2—C15 | 115.3 (3) | C28—C27—H27 | 119.6 |
C14—N2—C18 | 115.0 (3) | C26—C27—H27 | 119.6 |
C15—N2—C18 | 108.7 (3) | O5—C8—H8A | 109.5 |
C27—C28—C29 | 120.7 (3) | O5—C8—H8B | 109.5 |
C27—C28—H28 | 119.6 | H8A—C8—H8B | 109.5 |
C29—C28—H28 | 119.6 | O5—C8—H8C | 109.5 |
C30—C29—C28 | 119.5 (3) | H8A—C8—H8C | 109.5 |
C30—C29—H29 | 120.3 | H8B—C8—H8C | 109.5 |
C28—C29—H29 | 120.3 | C11—C12—C13 | 119.0 (4) |
C29—C30—C31 | 121.2 (3) | C11—C12—H12 | 120.5 |
C29—C30—H30 | 119.4 | C13—C12—H12 | 120.5 |
C31—C30—H30 | 119.4 | C14—C13—C12 | 122.4 (3) |
C30—C31—C22 | 122.5 (3) | C14—C13—H13 | 118.8 |
C30—C31—C26 | 119.9 (3) | C12—C13—H13 | 118.8 |
C22—C31—C26 | 117.6 (3) | N2—C15—C16 | 109.4 (3) |
C23—C22—O7 | 125.4 (3) | N2—C15—H15A | 109.8 |
C23—C22—C31 | 121.6 (4) | C16—C15—H15A | 109.8 |
O7—C22—C31 | 113.0 (3) | N2—C15—H15B | 109.8 |
O7—C21—C20 | 106.3 (3) | C16—C15—H15B | 109.8 |
O7—C21—H21A | 110.5 | H15A—C15—H15B | 108.2 |
C20—C21—H21A | 110.5 | N1—C16—C15 | 111.6 (3) |
O7—C21—H21B | 110.5 | N1—C16—H16A | 109.3 |
C20—C21—H21B | 110.5 | C15—C16—H16A | 109.3 |
H21A—C21—H21B | 108.7 | N1—C16—H16B | 109.3 |
O6—C20—C21 | 112.9 (3) | C15—C16—H16B | 109.3 |
O6—C20—C19 | 111.1 (3) | H16A—C16—H16B | 108.0 |
C21—C20—C19 | 109.7 (3) | C5A—C4—C3A | 119.8 (3) |
O6—C20—H20 | 107.7 | C5B—C4—C3B | 119.8 (3) |
C21—C20—H20 | 107.7 | C5A—C4—H4A | 120.1 |
C19—C20—H20 | 107.7 | C3A—C4—H4A | 120.1 |
N1—C19—C20 | 114.0 (3) | C5B—C4—H4B | 120.1 |
N1—C19—H19A | 108.7 | C3B—C4—H4B | 120.1 |
C20—C19—H19A | 108.7 | C7—C2—C3A | 118.3 (3) |
N1—C19—H19B | 108.7 | C7—C2—C3B | 118.3 (3) |
C20—C19—H19B | 108.7 | C7—C2—C1 | 120.8 (3) |
H19A—C19—H19B | 107.6 | C3A—C2—C1 | 120.9 (3) |
N1—C17—C18 | 111.6 (3) | C3B—C2—C1 | 120.9 (3) |
N1—C17—H17A | 109.3 | O1—C1—O2 | 123.3 (3) |
C18—C17—H17A | 109.3 | O1—C1—C2 | 118.9 (3) |
N1—C17—H17B | 109.3 | O2—C1—C2 | 117.8 (3) |
C18—C17—H17B | 109.3 | C5B—C6—C7 | 118.6 (4) |
H17A—C17—H17B | 108.0 | C5A—C6—C7 | 118.6 (4) |
N2—C18—C17 | 110.4 (3) | C5A—C6—H6A | 120.7 |
N2—C18—H18A | 109.6 | C7—C6—H6A | 120.7 |
C17—C18—H18A | 109.6 | C5B—C6—H6B | 120.7 |
N2—C18—H18B | 109.6 | C7—C6—H6B | 120.7 |
C17—C18—H18B | 109.6 | C6—C7—C2 | 122.0 (3) |
H18A—C18—H18B | 108.1 | C6—C7—H7 | 119.0 |
C13—C14—C9 | 118.0 (3) | C2—C7—H7 | 119.0 |
C13—C14—N2 | 123.4 (3) | ||
C27—C28—C29—C30 | −0.7 (5) | C22—C31—C26—C27 | 177.5 (3) |
C28—C29—C30—C31 | −1.4 (5) | C30—C31—C26—C25 | −176.3 (3) |
C29—C30—C31—C22 | −175.8 (3) | C22—C31—C26—C25 | 1.3 (4) |
C29—C30—C31—C26 | 1.8 (5) | C29—C28—C27—C26 | 2.4 (5) |
C21—O7—C22—C23 | 8.6 (5) | C25—C26—C27—C28 | 174.2 (3) |
C21—O7—C22—C31 | −172.3 (3) | C31—C26—C27—C28 | −2.0 (5) |
C30—C31—C22—C23 | 172.3 (3) | C10—C11—C12—C13 | 0.0 (5) |
C26—C31—C22—C23 | −5.3 (4) | C9—C14—C13—C12 | −0.9 (5) |
C30—C31—C22—O7 | −6.9 (4) | N2—C14—C13—C12 | −177.3 (3) |
C26—C31—C22—O7 | 175.5 (3) | C11—C12—C13—C14 | 0.4 (5) |
C22—O7—C21—C20 | 165.7 (3) | C14—N2—C15—C16 | 165.3 (2) |
O7—C21—C20—O6 | 58.0 (4) | C18—N2—C15—C16 | −63.9 (3) |
O7—C21—C20—C19 | −66.4 (4) | C19—N1—C16—C15 | −174.4 (2) |
C16—N1—C19—C20 | −178.9 (2) | C17—N1—C16—C15 | −50.5 (3) |
C17—N1—C19—C20 | 57.6 (3) | N2—C15—C16—N1 | 58.0 (3) |
O6—C20—C19—N1 | 49.7 (3) | C6—C5B—C4—C3B | 0.1 (5) |
C21—C20—C19—N1 | 175.2 (2) | O4—C5A—C4—C3A | 174.6 (7) |
C19—N1—C17—C18 | 171.6 (2) | C6—C5A—C4—C3A | 0.1 (5) |
C16—N1—C17—C18 | 49.5 (3) | O3—C3A—C4—C5A | −179.8 (3) |
C14—N2—C18—C17 | −165.6 (3) | C2—C3A—C4—C5A | 0.2 (5) |
C15—N2—C18—C17 | 63.4 (3) | C2—C3B—C4—C5B | 0.2 (5) |
N1—C17—C18—N2 | −56.3 (3) | O3—C3A—C2—C7 | 179.8 (3) |
C15—N2—C14—C13 | 12.7 (4) | C4—C3A—C2—C7 | −0.2 (5) |
C18—N2—C14—C13 | −115.0 (4) | O3—C3A—C2—C1 | −3.1 (5) |
C15—N2—C14—C9 | −163.7 (3) | C4—C3A—C2—C1 | 176.9 (3) |
C18—N2—C14—C9 | 68.6 (4) | C4—C3B—C2—C7 | −0.2 (5) |
C8—O5—C9—C10 | 1.8 (4) | C4—C3B—C2—C1 | 176.9 (3) |
C8—O5—C9—C14 | 179.9 (3) | C7—C2—C1—O1 | −3.6 (5) |
C13—C14—C9—O5 | −177.4 (3) | C3A—C2—C1—O1 | 179.4 (3) |
N2—C14—C9—O5 | −0.7 (4) | C3B—C2—C1—O1 | 179.4 (3) |
C13—C14—C9—C10 | 0.9 (4) | C7—C2—C1—O2 | 175.9 (3) |
N2—C14—C9—C10 | 177.5 (3) | C3A—C2—C1—O2 | −1.1 (5) |
O5—C9—C10—C11 | 177.6 (3) | C3B—C2—C1—O2 | −1.1 (5) |
C14—C9—C10—C11 | −0.5 (5) | C4—C5B—C6—C7 | −0.4 (5) |
C9—C10—C11—C12 | 0.0 (5) | O4—C5A—C6—C7 | −176.0 (6) |
O7—C22—C23—C24 | −176.9 (3) | C4—C5A—C6—C7 | −0.4 (5) |
C31—C22—C23—C24 | 4.0 (5) | C5B—C6—C7—C2 | 0.4 (5) |
C22—C23—C24—C25 | 1.4 (5) | C5A—C6—C7—C2 | 0.4 (5) |
C23—C24—C25—C26 | −5.3 (5) | C3A—C2—C7—C6 | −0.1 (5) |
C24—C25—C26—C27 | −172.2 (3) | C3B—C2—C7—C6 | −0.1 (5) |
C24—C25—C26—C31 | 3.8 (5) | C1—C2—C7—C6 | −177.2 (3) |
C30—C31—C26—C27 | −0.1 (4) |
C31H34N2O6.27 | F(000) = 1137 |
Mr = 534.92 | Dx = 1.313 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.369 (4) Å | Cell parameters from 9908 reflections |
b = 17.660 (6) Å | θ = 2.5–28.9° |
c = 13.539 (5) Å | µ = 0.09 mm−1 |
β = 95.632 (17)° | T = 293 K |
V = 2705.1 (16) Å3 | Block, colourless |
Z = 4 | 0.2 × 0.1 × 0.1 mm |
Bruker APEX-II CCD diffractometer | Rint = 0.050 |
φ and ω scans | θmax = 30.5°, θmin = 2.3° |
90604 measured reflections | h = −16→16 |
8175 independent reflections | k = −25→24 |
5373 reflections with I > 2σ(I) | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.089 | H-atom parameters constrained |
wR(F2) = 0.190 | w = 1/[σ2(Fo2) + (0.0292P)2 + 2.3128P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
8175 reflections | Δρmax = 0.15 e Å−3 |
365 parameters | Δρmin = −0.18 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C3A | 0.5588 (3) | 0.04324 (16) | 0.39454 (19) | 0.0676 (7) | 0.9 |
C7A | 0.3562 (3) | 0.07667 (16) | 0.3680 (2) | 0.0712 (8) | 0.37 |
O3 | 0.6704 (2) | 0.05624 (17) | 0.4286 (2) | 0.1004 (9) | 0.9 |
H3 | 0.676161 | 0.098760 | 0.452935 | 0.151* | 0.9 |
O4 | 0.2864 (7) | 0.1194 (5) | 0.3730 (8) | 0.143 (3) | 0.37 |
H7A | 0.222843 | 0.102083 | 0.349220 | 0.214* | 0.37 |
C3B | 0.5588 (3) | 0.04324 (16) | 0.39454 (19) | 0.0676 (7) | 0.1 |
H3B | 0.636068 | 0.053687 | 0.419841 | 0.081* | 0.1 |
C7B | 0.3562 (3) | 0.07667 (16) | 0.3680 (2) | 0.0712 (8) | 0.63 |
H7B | 0.295107 | 0.110338 | 0.376539 | 0.085* | 0.63 |
O1 | 0.41039 (19) | 0.21055 (10) | 0.47602 (17) | 0.0803 (6) | |
N003 | 0.49405 (18) | 0.34429 (9) | 0.55399 (14) | 0.0504 (5) | |
H003 | 0.465096 | 0.292713 | 0.540283 | 0.060* | |
O6 | 0.5582 (2) | 0.22964 (11) | 0.70105 (15) | 0.0826 (6) | |
H6 | 0.578204 | 0.206378 | 0.653016 | 0.124* | |
O7 | 0.8013 (2) | 0.24220 (12) | 0.69352 (16) | 0.0825 (6) | |
O2 | 0.5981 (2) | 0.17731 (12) | 0.50434 (17) | 0.0851 (6) | |
N007 | 0.31244 (18) | 0.44281 (10) | 0.46302 (14) | 0.0525 (5) | |
C14 | 0.2090 (2) | 0.47690 (13) | 0.41270 (18) | 0.0549 (6) | |
C9 | 0.1538 (2) | 0.53680 (13) | 0.4592 (2) | 0.0583 (6) | |
C16 | 0.5028 (2) | 0.38321 (13) | 0.45682 (18) | 0.0558 (6) | |
H16A | 0.549211 | 0.352201 | 0.416001 | 0.067* | |
H16B | 0.543636 | 0.431083 | 0.468553 | 0.067* | |
C15 | 0.3837 (2) | 0.39754 (14) | 0.40198 (18) | 0.0588 (6) | |
H15A | 0.392922 | 0.423986 | 0.340429 | 0.071* | |
H15B | 0.344417 | 0.349713 | 0.385870 | 0.071* | |
C1 | 0.4938 (3) | 0.16592 (14) | 0.4665 (2) | 0.0628 (7) | |
C2 | 0.4696 (2) | 0.09445 (12) | 0.40743 (17) | 0.0543 (6) | |
C17 | 0.4076 (2) | 0.38404 (13) | 0.61245 (18) | 0.0587 (6) | |
H17A | 0.441374 | 0.431767 | 0.636732 | 0.070* | |
H17B | 0.393384 | 0.353344 | 0.669485 | 0.070* | |
C19 | 0.6135 (2) | 0.33905 (13) | 0.6090 (2) | 0.0613 (6) | |
H19A | 0.644846 | 0.389859 | 0.619157 | 0.074* | |
H19B | 0.665087 | 0.312079 | 0.568110 | 0.074* | |
C18 | 0.2925 (2) | 0.39892 (14) | 0.55190 (19) | 0.0602 (6) | |
H18A | 0.254704 | 0.351223 | 0.532458 | 0.072* | |
H18B | 0.240326 | 0.426764 | 0.591368 | 0.072* | |
C10 | 0.0554 (3) | 0.57162 (16) | 0.4106 (2) | 0.0717 (8) | |
H10 | 0.018127 | 0.610514 | 0.441863 | 0.086* | |
C13 | 0.1631 (3) | 0.45624 (16) | 0.3181 (2) | 0.0691 (7) | |
H13 | 0.198840 | 0.417033 | 0.286229 | 0.083* | |
C20 | 0.6177 (3) | 0.29975 (14) | 0.7091 (2) | 0.0706 (8) | |
H20 | 0.575598 | 0.332040 | 0.752891 | 0.085* | |
C31 | 0.9701 (3) | 0.19218 (16) | 0.6313 (2) | 0.0723 (8) | |
C30 | 0.8990 (3) | 0.15141 (19) | 0.5596 (2) | 0.0779 (8) | |
H30 | 0.817159 | 0.155441 | 0.556963 | 0.093* | |
C11 | 0.0120 (3) | 0.54930 (18) | 0.3166 (3) | 0.0814 (9) | |
H11 | −0.054150 | 0.573188 | 0.284867 | 0.098* | |
C22 | 0.9222 (3) | 0.23705 (15) | 0.7046 (3) | 0.0805 (9) | |
C5 | 0.4202 (4) | −0.03932 (17) | 0.3051 (2) | 0.0892 (11) | |
H5 | 0.403948 | −0.084267 | 0.270607 | 0.107* | |
C12 | 0.0658 (3) | 0.49202 (18) | 0.2695 (2) | 0.0809 (9) | |
H12 | 0.037268 | 0.477422 | 0.205577 | 0.097* | |
C6 | 0.3310 (4) | 0.01012 (18) | 0.3161 (2) | 0.0848 (10) | |
H6A | 0.254360 | −0.000512 | 0.289244 | 0.102* | 0.37 |
H6B | 0.254360 | −0.000512 | 0.289244 | 0.102* | 0.63 |
C4 | 0.5322 (4) | −0.02447 (17) | 0.3432 (2) | 0.0844 (10) | |
H4A | 0.591815 | −0.059344 | 0.335317 | 0.101* | 0.9 |
H4B | 0.591815 | −0.059344 | 0.335317 | 0.101* | 0.1 |
C8 | 0.1530 (3) | 0.61906 (17) | 0.5994 (3) | 0.0872 (10) | |
H8A | 0.152278 | 0.663179 | 0.557948 | 0.131* | |
H8B | 0.198291 | 0.629310 | 0.661627 | 0.131* | |
H8C | 0.073485 | 0.606222 | 0.611058 | 0.131* | |
C21 | 0.7431 (3) | 0.29260 (17) | 0.7549 (2) | 0.0878 (10) | |
H21A | 0.781589 | 0.341670 | 0.757768 | 0.105* | |
H21B | 0.744922 | 0.272615 | 0.821738 | 0.105* | |
C26 | 1.0954 (3) | 0.1873 (2) | 0.6322 (3) | 0.0881 (11) | |
C27 | 1.1416 (3) | 0.1408 (3) | 0.5610 (3) | 0.1036 (13) | |
H27 | 1.223140 | 0.137761 | 0.559713 | 0.124* | |
C25 | 1.1662 (4) | 0.2253 (2) | 0.7076 (4) | 0.1167 (16) | |
H25 | 1.248035 | 0.223866 | 0.707963 | 0.140* | |
C29 | 0.9484 (3) | 0.1058 (2) | 0.4934 (3) | 0.0954 (11) | |
H29 | 0.899896 | 0.077993 | 0.447479 | 0.114* | |
C23 | 0.9930 (4) | 0.27006 (18) | 0.7795 (3) | 0.1129 (15) | |
H23 | 0.960443 | 0.296279 | 0.829807 | 0.135* | |
C24 | 1.1173 (5) | 0.2636 (2) | 0.7792 (5) | 0.136 (2) | |
H24 | 1.166259 | 0.286481 | 0.829723 | 0.163* | |
C28 | 1.0706 (4) | 0.1004 (3) | 0.4940 (3) | 0.1106 (14) | |
H28 | 1.103472 | 0.069234 | 0.448696 | 0.133* | |
O5 | 0.20532 (17) | 0.55699 (10) | 0.55111 (14) | 0.0701 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C3A | 0.096 (2) | 0.0605 (15) | 0.0467 (13) | 0.0077 (15) | 0.0098 (13) | −0.0044 (11) |
C7A | 0.094 (2) | 0.0575 (15) | 0.0637 (16) | −0.0114 (15) | 0.0132 (15) | −0.0014 (13) |
O3 | 0.0940 (19) | 0.110 (2) | 0.0962 (19) | 0.0263 (16) | 0.0046 (15) | −0.0374 (17) |
O4 | 0.094 (5) | 0.146 (7) | 0.189 (9) | 0.046 (5) | 0.014 (6) | −0.053 (7) |
C3B | 0.096 (2) | 0.0605 (15) | 0.0467 (13) | 0.0077 (15) | 0.0098 (13) | −0.0044 (11) |
C7B | 0.094 (2) | 0.0575 (15) | 0.0637 (16) | −0.0114 (15) | 0.0132 (15) | −0.0014 (13) |
O1 | 0.0873 (14) | 0.0493 (10) | 0.1071 (16) | 0.0033 (10) | 0.0242 (12) | −0.0200 (10) |
N003 | 0.0679 (12) | 0.0308 (8) | 0.0543 (11) | 0.0050 (8) | 0.0164 (9) | −0.0010 (7) |
O6 | 0.1304 (19) | 0.0512 (10) | 0.0691 (13) | 0.0091 (11) | 0.0248 (12) | 0.0063 (9) |
O7 | 0.0937 (16) | 0.0671 (12) | 0.0826 (14) | 0.0181 (11) | −0.0115 (11) | −0.0170 (10) |
O2 | 0.0823 (15) | 0.0732 (13) | 0.1002 (16) | −0.0071 (11) | 0.0108 (12) | −0.0317 (12) |
N007 | 0.0647 (12) | 0.0442 (10) | 0.0501 (10) | 0.0081 (9) | 0.0139 (9) | −0.0011 (8) |
C14 | 0.0631 (15) | 0.0433 (11) | 0.0595 (14) | 0.0056 (11) | 0.0128 (11) | 0.0001 (10) |
C9 | 0.0654 (15) | 0.0452 (12) | 0.0652 (15) | 0.0027 (11) | 0.0111 (12) | 0.0002 (11) |
C16 | 0.0677 (16) | 0.0448 (11) | 0.0582 (14) | 0.0076 (11) | 0.0221 (12) | 0.0022 (10) |
C15 | 0.0733 (17) | 0.0551 (13) | 0.0499 (13) | 0.0100 (12) | 0.0163 (12) | −0.0042 (10) |
C1 | 0.0841 (19) | 0.0460 (12) | 0.0618 (15) | −0.0090 (13) | 0.0253 (14) | −0.0059 (11) |
C2 | 0.0798 (17) | 0.0392 (11) | 0.0466 (12) | −0.0030 (11) | 0.0187 (11) | 0.0004 (9) |
C17 | 0.0830 (18) | 0.0446 (12) | 0.0511 (13) | 0.0147 (12) | 0.0205 (12) | 0.0003 (10) |
C19 | 0.0762 (17) | 0.0389 (11) | 0.0687 (16) | 0.0048 (11) | 0.0068 (13) | −0.0003 (11) |
C18 | 0.0758 (17) | 0.0483 (12) | 0.0600 (14) | 0.0094 (12) | 0.0240 (13) | 0.0038 (11) |
C10 | 0.0709 (18) | 0.0548 (15) | 0.091 (2) | 0.0146 (13) | 0.0147 (16) | 0.0041 (14) |
C13 | 0.0823 (19) | 0.0608 (15) | 0.0635 (16) | 0.0036 (14) | 0.0031 (14) | −0.0052 (13) |
C20 | 0.107 (2) | 0.0460 (13) | 0.0590 (15) | 0.0190 (14) | 0.0087 (15) | −0.0077 (11) |
C31 | 0.077 (2) | 0.0584 (15) | 0.0792 (19) | 0.0033 (14) | −0.0030 (15) | 0.0257 (14) |
C30 | 0.0743 (19) | 0.095 (2) | 0.0641 (17) | 0.0127 (17) | 0.0035 (15) | 0.0057 (16) |
C11 | 0.077 (2) | 0.0709 (19) | 0.094 (2) | 0.0072 (16) | −0.0048 (17) | 0.0171 (17) |
C22 | 0.092 (2) | 0.0448 (14) | 0.099 (2) | 0.0063 (14) | −0.0235 (18) | 0.0099 (15) |
C5 | 0.167 (4) | 0.0494 (15) | 0.0498 (15) | −0.017 (2) | 0.0035 (19) | −0.0002 (12) |
C12 | 0.088 (2) | 0.078 (2) | 0.0740 (19) | 0.0041 (17) | −0.0078 (16) | 0.0049 (16) |
C6 | 0.121 (3) | 0.0653 (18) | 0.0673 (18) | −0.0248 (19) | 0.0063 (18) | −0.0060 (14) |
C4 | 0.144 (3) | 0.0581 (16) | 0.0520 (15) | 0.0285 (19) | 0.0118 (18) | −0.0063 (13) |
C8 | 0.107 (3) | 0.0674 (18) | 0.090 (2) | 0.0261 (17) | 0.0218 (19) | −0.0196 (16) |
C21 | 0.129 (3) | 0.0567 (16) | 0.0727 (19) | 0.0232 (18) | −0.0158 (19) | −0.0124 (14) |
C26 | 0.078 (2) | 0.073 (2) | 0.110 (3) | −0.0073 (17) | −0.007 (2) | 0.045 (2) |
C27 | 0.068 (2) | 0.130 (3) | 0.114 (3) | 0.006 (2) | 0.020 (2) | 0.053 (3) |
C25 | 0.090 (3) | 0.070 (2) | 0.182 (5) | −0.013 (2) | −0.031 (3) | 0.040 (3) |
C29 | 0.082 (2) | 0.134 (3) | 0.072 (2) | 0.015 (2) | 0.0155 (17) | −0.003 (2) |
C23 | 0.134 (4) | 0.0529 (17) | 0.138 (3) | 0.005 (2) | −0.054 (3) | −0.0101 (19) |
C24 | 0.134 (4) | 0.058 (2) | 0.198 (5) | −0.015 (2) | −0.072 (4) | 0.005 (3) |
C28 | 0.083 (3) | 0.160 (4) | 0.092 (3) | 0.014 (3) | 0.024 (2) | 0.023 (3) |
O5 | 0.0809 (13) | 0.0565 (10) | 0.0735 (12) | 0.0175 (9) | 0.0112 (10) | −0.0158 (9) |
C3A—O3 | 1.328 (4) | C18—H18A | 0.9700 |
C3A—C2 | 1.382 (4) | C18—H18B | 0.9700 |
C3A—C4 | 1.401 (4) | C10—C11 | 1.377 (4) |
C7A—O4 | 1.102 (7) | C10—H10 | 0.9300 |
C7A—C2 | 1.382 (4) | C13—C12 | 1.384 (4) |
C7A—C6 | 1.385 (4) | C13—H13 | 0.9300 |
O3—H3 | 0.8200 | C20—C21 | 1.503 (4) |
O4—H7A | 0.8200 | C20—H20 | 0.9800 |
C3B—C2 | 1.382 (4) | C31—C30 | 1.401 (4) |
C3B—C4 | 1.401 (4) | C31—C22 | 1.419 (5) |
C3B—H3B | 0.9300 | C31—C26 | 1.426 (5) |
C7B—C2 | 1.382 (4) | C30—C29 | 1.366 (4) |
C7B—C6 | 1.385 (4) | C30—H30 | 0.9300 |
C7B—H7B | 0.9300 | C11—C12 | 1.372 (4) |
O1—C1 | 1.249 (3) | C11—H11 | 0.9300 |
N003—C19 | 1.487 (3) | C22—C23 | 1.362 (4) |
N003—C17 | 1.496 (3) | C5—C4 | 1.352 (5) |
N003—C16 | 1.496 (3) | C5—C6 | 1.357 (5) |
N003—H003 | 0.9800 | C5—H5 | 0.9300 |
O6—C20 | 1.410 (3) | C12—H12 | 0.9300 |
O6—H6 | 0.8200 | C6—H6A | 0.9300 |
O7—C22 | 1.372 (4) | C6—H6B | 0.9300 |
O7—C21 | 1.424 (4) | C4—H4A | 0.9300 |
O2—C1 | 1.261 (3) | C4—H4B | 0.9300 |
N007—C14 | 1.432 (3) | C8—O5 | 1.435 (3) |
N007—C15 | 1.452 (3) | C8—H8A | 0.9600 |
N007—C18 | 1.468 (3) | C8—H8B | 0.9600 |
C14—C13 | 1.383 (4) | C8—H8C | 0.9600 |
C14—C9 | 1.410 (3) | C21—H21A | 0.9700 |
C9—O5 | 1.369 (3) | C21—H21B | 0.9700 |
C9—C10 | 1.386 (4) | C26—C27 | 1.407 (6) |
C16—C15 | 1.501 (4) | C26—C25 | 1.406 (6) |
C16—H16A | 0.9700 | C27—C28 | 1.356 (6) |
C16—H16B | 0.9700 | C27—H27 | 0.9300 |
C15—H15A | 0.9700 | C25—C24 | 1.347 (7) |
C15—H15B | 0.9700 | C25—H25 | 0.9300 |
C1—C2 | 1.505 (3) | C29—C28 | 1.392 (5) |
C17—C18 | 1.498 (4) | C29—H29 | 0.9300 |
C17—H17A | 0.9700 | C23—C24 | 1.418 (7) |
C17—H17B | 0.9700 | C23—H23 | 0.9300 |
C19—C20 | 1.519 (4) | C24—H24 | 0.9300 |
C19—H19A | 0.9700 | C28—H28 | 0.9300 |
C19—H19B | 0.9700 | ||
O3—C3A—C2 | 122.1 (3) | C12—C13—C14 | 122.1 (3) |
O3—C3A—C4 | 118.2 (3) | C12—C13—H13 | 118.9 |
C2—C3A—C4 | 119.7 (3) | C14—C13—H13 | 118.9 |
O4—C7A—C2 | 118.1 (5) | O6—C20—C21 | 112.7 (2) |
O4—C7A—C6 | 119.9 (6) | O6—C20—C19 | 111.1 (2) |
C2—C7A—C6 | 121.8 (3) | C21—C20—C19 | 110.5 (3) |
C3A—O3—H3 | 109.5 | O6—C20—H20 | 107.4 |
C7A—O4—H7A | 109.5 | C21—C20—H20 | 107.4 |
C2—C3B—C4 | 119.7 (3) | C19—C20—H20 | 107.4 |
C2—C3B—H3B | 120.1 | C30—C31—C22 | 122.4 (3) |
C4—C3B—H3B | 120.1 | C30—C31—C26 | 118.9 (3) |
C2—C7B—C6 | 121.8 (3) | C22—C31—C26 | 118.6 (3) |
C2—C7B—H7B | 119.1 | C29—C30—C31 | 120.7 (3) |
C6—C7B—H7B | 119.1 | C29—C30—H30 | 119.6 |
C19—N003—C17 | 112.30 (19) | C31—C30—H30 | 119.6 |
C19—N003—C16 | 109.45 (19) | C12—C11—C10 | 120.4 (3) |
C17—N003—C16 | 110.70 (17) | C12—C11—H11 | 119.8 |
C19—N003—H003 | 108.1 | C10—C11—H11 | 119.8 |
C17—N003—H003 | 108.1 | C23—C22—O7 | 124.4 (4) |
C16—N003—H003 | 108.1 | C23—C22—C31 | 121.3 (4) |
C20—O6—H6 | 109.5 | O7—C22—C31 | 114.2 (3) |
C22—O7—C21 | 119.7 (3) | C4—C5—C6 | 121.3 (3) |
C14—N007—C15 | 115.99 (19) | C4—C5—H5 | 119.4 |
C14—N007—C18 | 115.2 (2) | C6—C5—H5 | 119.4 |
C15—N007—C18 | 108.40 (18) | C11—C12—C13 | 119.2 (3) |
C13—C14—C9 | 117.9 (2) | C11—C12—H12 | 120.4 |
C13—C14—N007 | 123.1 (2) | C13—C12—H12 | 120.4 |
C9—C14—N007 | 118.9 (2) | C5—C6—C7A | 118.8 (3) |
O5—C9—C10 | 124.7 (2) | C5—C6—C7B | 118.8 (3) |
O5—C9—C14 | 115.6 (2) | C5—C6—H6A | 120.6 |
C10—C9—C14 | 119.7 (3) | C7A—C6—H6A | 120.6 |
N003—C16—C15 | 112.2 (2) | C5—C6—H6B | 120.6 |
N003—C16—H16A | 109.2 | C7B—C6—H6B | 120.6 |
C15—C16—H16A | 109.2 | C5—C4—C3A | 120.3 (3) |
N003—C16—H16B | 109.2 | C5—C4—C3B | 120.3 (3) |
C15—C16—H16B | 109.2 | C5—C4—H4A | 119.9 |
H16A—C16—H16B | 107.9 | C3A—C4—H4A | 119.9 |
N007—C15—C16 | 109.7 (2) | C5—C4—H4B | 119.9 |
N007—C15—H15A | 109.7 | C3B—C4—H4B | 119.9 |
C16—C15—H15A | 109.7 | O5—C8—H8A | 109.5 |
N007—C15—H15B | 109.7 | O5—C8—H8B | 109.5 |
C16—C15—H15B | 109.7 | H8A—C8—H8B | 109.5 |
H15A—C15—H15B | 108.2 | O5—C8—H8C | 109.5 |
O1—C1—O2 | 123.4 (2) | H8A—C8—H8C | 109.5 |
O1—C1—C2 | 118.9 (3) | H8B—C8—H8C | 109.5 |
O2—C1—C2 | 117.7 (2) | O7—C21—C20 | 106.8 (2) |
C3B—C2—C7B | 118.1 (2) | O7—C21—H21A | 110.4 |
C3A—C2—C7A | 118.1 (2) | C20—C21—H21A | 110.4 |
C3B—C2—C1 | 121.2 (3) | O7—C21—H21B | 110.4 |
C3A—C2—C1 | 121.2 (3) | C20—C21—H21B | 110.4 |
C7B—C2—C1 | 120.7 (2) | H21A—C21—H21B | 108.6 |
C7A—C2—C1 | 120.7 (2) | C27—C26—C25 | 123.4 (4) |
N003—C17—C18 | 112.1 (2) | C27—C26—C31 | 118.0 (4) |
N003—C17—H17A | 109.2 | C25—C26—C31 | 118.5 (4) |
C18—C17—H17A | 109.2 | C28—C27—C26 | 121.8 (4) |
N003—C17—H17B | 109.2 | C28—C27—H27 | 119.1 |
C18—C17—H17B | 109.2 | C26—C27—H27 | 119.1 |
H17A—C17—H17B | 107.9 | C24—C25—C26 | 121.0 (4) |
N003—C19—C20 | 115.0 (2) | C24—C25—H25 | 119.5 |
N003—C19—H19A | 108.5 | C26—C25—H25 | 119.5 |
C20—C19—H19A | 108.5 | C30—C29—C28 | 120.7 (4) |
N003—C19—H19B | 108.5 | C30—C29—H29 | 119.6 |
C20—C19—H19B | 108.5 | C28—C29—H29 | 119.6 |
H19A—C19—H19B | 107.5 | C22—C23—C24 | 118.7 (5) |
N007—C18—C17 | 110.1 (2) | C22—C23—H23 | 120.7 |
N007—C18—H18A | 109.6 | C24—C23—H23 | 120.7 |
C17—C18—H18A | 109.6 | C25—C24—C23 | 121.6 (4) |
N007—C18—H18B | 109.6 | C25—C24—H24 | 119.2 |
C17—C18—H18B | 109.6 | C23—C24—H24 | 119.2 |
H18A—C18—H18B | 108.1 | C27—C28—C29 | 119.8 (4) |
C11—C10—C9 | 120.7 (3) | C27—C28—H28 | 120.1 |
C11—C10—H10 | 119.6 | C29—C28—H28 | 120.1 |
C9—C10—H10 | 119.6 | C9—O5—C8 | 117.0 (2) |
C31H34N2O6.46 | F(000) = 1143 |
Mr = 537.96 | Dx = 1.358 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.102 (5) Å | Cell parameters from 9948 reflections |
b = 17.701 (9) Å | θ = 2.7–28.3° |
c = 13.437 (6) Å | µ = 0.10 mm−1 |
β = 94.667 (18)° | T = 100 K |
V = 2632 (2) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.25 × 0.2 mm |
Bruker APEX-II CCD diffractometer | 5857 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 0.0755 before and 0.0567 after correction. The Ratio of minimum to maximum transmission is 0.9320. The λ/2 correction factor is Not present. | θmax = 28.3°, θmin = 2.2° |
Tmin = 0.695, Tmax = 0.746 | h = −14→14 |
61552 measured reflections | k = −23→23 |
6497 independent reflections | l = −17→17 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.099 | H-atom parameters constrained |
wR(F2) = 0.256 | w = 1/[σ2(Fo2) + (0.0627P)2 + 15.8476P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.005 |
6497 reflections | Δρmax = 0.41 e Å−3 |
375 parameters | Δρmin = −0.50 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C3A | 0.4537 (3) | 0.5429 (2) | 0.6012 (3) | 0.0261 (8) | 0.73 |
C4A | 0.4796 (4) | 0.4743 (2) | 0.6512 (3) | 0.0275 (8) | 0.37 |
C5A | 0.5939 (4) | 0.4610 (2) | 0.6950 (3) | 0.0272 (8) | 0.36 |
O3 | 0.3431 (3) | 0.5513 (3) | 0.5623 (3) | 0.0396 (10) | 0.73 |
H3 | 0.335817 | 0.593792 | 0.534586 | 0.059* | 0.73 |
O4 | 0.3898 (7) | 0.4252 (4) | 0.6529 (6) | 0.0330 (17) | 0.37 |
H4 | 0.332829 | 0.438416 | 0.611647 | 0.050* | 0.37 |
O5 | 0.6361 (7) | 0.4015 (4) | 0.7520 (6) | 0.0283 (16) | 0.36 |
H5 | 0.630489 | 0.361741 | 0.717865 | 0.042* | 0.36 |
C3B | 0.4537 (3) | 0.5429 (2) | 0.6012 (3) | 0.0261 (8) | 0.27 |
H3B | 0.374461 | 0.552103 | 0.571572 | 0.031* | 0.27 |
C4B | 0.4796 (4) | 0.4743 (2) | 0.6512 (3) | 0.0275 (8) | 0.63 |
H4B | 0.418163 | 0.437234 | 0.654761 | 0.033* | 0.63 |
C5B | 0.5939 (4) | 0.4610 (2) | 0.6950 (3) | 0.0272 (8) | 0.64 |
H5B | 0.611149 | 0.414591 | 0.728793 | 0.033* | 0.64 |
O6 | 0.1958 (3) | −0.05880 (15) | 0.5443 (2) | 0.0273 (6) | |
O8 | 0.7947 (3) | 0.26201 (16) | 0.6923 (2) | 0.0321 (7) | |
O7 | 0.5439 (3) | 0.27042 (16) | 0.6958 (3) | 0.0376 (7) | |
H7 | 0.565045 | 0.293203 | 0.645189 | 0.056* | |
O2 | 0.4134 (3) | 0.67619 (18) | 0.4930 (3) | 0.0407 (8) | |
O1 | 0.5996 (3) | 0.71662 (15) | 0.5322 (2) | 0.0349 (7) | |
N1 | 0.3109 (3) | 0.05408 (17) | 0.4564 (2) | 0.0231 (6) | |
N2 | 0.4912 (3) | 0.15386 (16) | 0.5499 (2) | 0.0225 (6) | |
H2 | 0.460143 | 0.205895 | 0.534103 | 0.027* | |
C8 | 0.1360 (4) | −0.1186 (2) | 0.5934 (3) | 0.0291 (8) | |
H8A | 0.138666 | −0.164988 | 0.553923 | 0.044* | |
H8B | 0.051618 | −0.104427 | 0.599858 | 0.044* | |
H8C | 0.176870 | −0.126989 | 0.659880 | 0.044* | |
C9 | 0.1478 (3) | −0.03908 (19) | 0.4510 (3) | 0.0227 (7) | |
C31 | 0.2070 (3) | 0.02070 (19) | 0.4045 (3) | 0.0230 (7) | |
C14 | 0.3866 (4) | 0.0991 (2) | 0.3954 (3) | 0.0287 (8) | |
H14A | 0.346085 | 0.147630 | 0.377615 | 0.034* | |
H14B | 0.399386 | 0.071732 | 0.332899 | 0.034* | |
C15 | 0.5067 (4) | 0.1139 (2) | 0.4531 (3) | 0.0273 (8) | |
H15A | 0.548811 | 0.065265 | 0.467021 | 0.033* | |
H15B | 0.557547 | 0.145086 | 0.411955 | 0.033* | |
C18 | 0.6115 (4) | 0.1608 (2) | 0.6074 (3) | 0.0260 (8) | |
H18A | 0.666848 | 0.188567 | 0.566292 | 0.031* | |
H18B | 0.645260 | 0.109605 | 0.619744 | 0.031* | |
C19 | 0.6074 (4) | 0.2013 (2) | 0.7072 (3) | 0.0272 (8) | |
H19 | 0.562605 | 0.168210 | 0.751811 | 0.033* | |
C20 | 0.7353 (4) | 0.2113 (2) | 0.7556 (3) | 0.0298 (8) | |
H20A | 0.733538 | 0.232838 | 0.823498 | 0.036* | |
H20B | 0.777933 | 0.162160 | 0.760669 | 0.036* | |
C21 | 0.9174 (4) | 0.2672 (2) | 0.7023 (3) | 0.0261 (8) | |
C30 | 0.9659 (3) | 0.31094 (19) | 0.6256 (3) | 0.0216 (7) | |
C29 | 0.8907 (3) | 0.3510 (2) | 0.5540 (3) | 0.0235 (7) | |
H29 | 0.805349 | 0.346673 | 0.553499 | 0.028* | |
C28 | 0.9406 (3) | 0.3964 (2) | 0.4846 (3) | 0.0258 (7) | |
H28 | 0.889649 | 0.425088 | 0.438659 | 0.031* | |
C27 | 1.0673 (4) | 0.4004 (2) | 0.4819 (3) | 0.0294 (8) | |
H27 | 1.101113 | 0.431095 | 0.433292 | 0.035* | |
C10 | 0.0497 (3) | −0.0749 (2) | 0.4006 (3) | 0.0254 (8) | |
H10 | 0.010046 | −0.114882 | 0.431985 | 0.030* | |
C11 | 0.0093 (4) | −0.0527 (2) | 0.3043 (3) | 0.0279 (8) | |
H11 | −0.057968 | −0.077565 | 0.270482 | 0.033* | |
C12 | 0.0659 (4) | 0.0053 (2) | 0.2572 (3) | 0.0302 (8) | |
H12 | 0.038221 | 0.020403 | 0.191411 | 0.036* | |
C13 | 0.1645 (4) | 0.0412 (2) | 0.3081 (3) | 0.0300 (8) | |
H13 | 0.203802 | 0.080905 | 0.275905 | 0.036* | |
C16 | 0.4016 (3) | 0.1142 (2) | 0.6085 (3) | 0.0228 (7) | |
H16A | 0.383711 | 0.145866 | 0.666255 | 0.027* | |
H16B | 0.436588 | 0.065990 | 0.634523 | 0.027* | |
C17 | 0.2857 (3) | 0.0984 (2) | 0.5450 (3) | 0.0248 (7) | |
H17A | 0.229434 | 0.070135 | 0.584705 | 0.030* | |
H17B | 0.246700 | 0.146748 | 0.523843 | 0.030* | |
C22 | 0.9915 (4) | 0.2357 (2) | 0.7779 (3) | 0.0303 (8) | |
H22 | 0.957927 | 0.209716 | 0.830967 | 0.036* | |
C23 | 1.1177 (4) | 0.2421 (2) | 0.7760 (3) | 0.0336 (9) | |
H23 | 1.168740 | 0.220859 | 0.828923 | 0.040* | |
C24 | 1.1686 (4) | 0.2782 (2) | 0.7000 (3) | 0.0291 (8) | |
H24 | 1.253938 | 0.278695 | 0.697884 | 0.035* | |
C25 | 1.0937 (3) | 0.3151 (2) | 0.6239 (3) | 0.0239 (7) | |
C26 | 1.1422 (4) | 0.3600 (2) | 0.5491 (3) | 0.0294 (8) | |
H26 | 1.227272 | 0.362171 | 0.545424 | 0.035* | |
C1 | 0.5173 (4) | 0.6691 (2) | 0.5364 (3) | 0.0291 (8) | |
C2 | 0.5430 (3) | 0.5972 (2) | 0.5947 (3) | 0.0233 (7) | |
C7 | 0.6581 (4) | 0.5824 (2) | 0.6402 (3) | 0.0280 (8) | |
H7A | 0.719830 | 0.619247 | 0.637004 | 0.034* | |
C6 | 0.6845 (4) | 0.5148 (2) | 0.6901 (3) | 0.0313 (8) | |
H6A | 0.763365 | 0.505576 | 0.720505 | 0.038* | 0.36 |
H6B | 0.763365 | 0.505576 | 0.720505 | 0.038* | 0.64 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C3A | 0.0268 (18) | 0.0296 (19) | 0.0225 (17) | 0.0006 (15) | 0.0052 (14) | 0.0046 (14) |
C4A | 0.037 (2) | 0.0224 (17) | 0.0241 (17) | −0.0082 (15) | 0.0070 (15) | −0.0001 (14) |
C5A | 0.040 (2) | 0.0202 (17) | 0.0222 (17) | 0.0011 (15) | 0.0059 (15) | 0.0005 (13) |
O3 | 0.0222 (19) | 0.050 (3) | 0.046 (2) | −0.0001 (18) | −0.0001 (17) | 0.020 (2) |
O4 | 0.034 (4) | 0.030 (4) | 0.035 (4) | −0.009 (3) | 0.000 (3) | 0.011 (3) |
O5 | 0.037 (4) | 0.020 (3) | 0.028 (4) | 0.004 (3) | −0.003 (3) | 0.007 (3) |
C3B | 0.0268 (18) | 0.0296 (19) | 0.0225 (17) | 0.0006 (15) | 0.0052 (14) | 0.0046 (14) |
C4B | 0.037 (2) | 0.0224 (17) | 0.0241 (17) | −0.0082 (15) | 0.0070 (15) | −0.0001 (14) |
C5B | 0.040 (2) | 0.0202 (17) | 0.0222 (17) | 0.0011 (15) | 0.0059 (15) | 0.0005 (13) |
O6 | 0.0337 (14) | 0.0213 (13) | 0.0277 (13) | −0.0034 (11) | 0.0076 (11) | 0.0058 (10) |
O8 | 0.0278 (14) | 0.0268 (14) | 0.0427 (16) | −0.0018 (11) | 0.0092 (12) | 0.0137 (12) |
O7 | 0.0373 (16) | 0.0214 (14) | 0.056 (2) | −0.0015 (12) | 0.0171 (14) | −0.0078 (13) |
O2 | 0.0362 (17) | 0.0342 (16) | 0.053 (2) | 0.0050 (13) | 0.0081 (14) | 0.0188 (14) |
O1 | 0.0425 (17) | 0.0186 (13) | 0.0449 (17) | −0.0029 (12) | 0.0118 (14) | 0.0042 (12) |
N1 | 0.0323 (16) | 0.0166 (13) | 0.0217 (14) | −0.0032 (12) | 0.0098 (12) | −0.0007 (11) |
N2 | 0.0302 (16) | 0.0145 (13) | 0.0242 (15) | −0.0010 (12) | 0.0103 (12) | −0.0005 (11) |
C8 | 0.032 (2) | 0.0223 (17) | 0.034 (2) | −0.0038 (15) | 0.0100 (16) | 0.0064 (15) |
C9 | 0.0256 (17) | 0.0165 (15) | 0.0270 (17) | 0.0046 (13) | 0.0086 (14) | 0.0000 (13) |
C31 | 0.0273 (18) | 0.0155 (15) | 0.0271 (17) | 0.0006 (13) | 0.0076 (14) | −0.0020 (13) |
C14 | 0.039 (2) | 0.0232 (17) | 0.0254 (18) | −0.0059 (16) | 0.0135 (16) | 0.0003 (14) |
C15 | 0.038 (2) | 0.0204 (17) | 0.0260 (18) | −0.0027 (15) | 0.0188 (16) | −0.0028 (14) |
C18 | 0.0307 (19) | 0.0166 (16) | 0.0315 (19) | 0.0015 (14) | 0.0078 (15) | 0.0011 (14) |
C19 | 0.033 (2) | 0.0188 (16) | 0.0313 (19) | −0.0054 (15) | 0.0105 (16) | −0.0012 (14) |
C20 | 0.040 (2) | 0.0209 (17) | 0.0288 (19) | −0.0066 (16) | 0.0063 (16) | 0.0034 (14) |
C21 | 0.033 (2) | 0.0142 (15) | 0.0313 (19) | 0.0001 (14) | 0.0049 (15) | −0.0030 (14) |
C30 | 0.0230 (17) | 0.0172 (15) | 0.0246 (17) | −0.0010 (13) | 0.0020 (13) | −0.0064 (13) |
C29 | 0.0208 (16) | 0.0231 (17) | 0.0267 (18) | −0.0029 (13) | 0.0025 (13) | −0.0030 (14) |
C28 | 0.0246 (18) | 0.0304 (19) | 0.0222 (17) | −0.0017 (15) | 0.0003 (14) | −0.0009 (14) |
C27 | 0.0282 (19) | 0.036 (2) | 0.0244 (18) | −0.0042 (16) | 0.0061 (15) | −0.0008 (16) |
C10 | 0.0262 (18) | 0.0145 (15) | 0.037 (2) | 0.0001 (13) | 0.0096 (15) | −0.0003 (14) |
C11 | 0.0293 (19) | 0.0192 (16) | 0.035 (2) | 0.0038 (14) | 0.0002 (15) | −0.0048 (15) |
C12 | 0.040 (2) | 0.0234 (18) | 0.0275 (19) | 0.0046 (16) | 0.0030 (16) | −0.0027 (15) |
C13 | 0.045 (2) | 0.0195 (17) | 0.0272 (19) | 0.0013 (16) | 0.0099 (16) | 0.0020 (14) |
C16 | 0.0267 (18) | 0.0192 (16) | 0.0242 (17) | −0.0043 (13) | 0.0122 (14) | −0.0013 (13) |
C17 | 0.0305 (19) | 0.0196 (16) | 0.0257 (17) | −0.0014 (14) | 0.0107 (14) | −0.0028 (14) |
C22 | 0.042 (2) | 0.0163 (16) | 0.033 (2) | 0.0024 (15) | 0.0018 (17) | 0.0025 (14) |
C23 | 0.042 (2) | 0.0192 (17) | 0.039 (2) | 0.0087 (16) | −0.0030 (18) | 0.0023 (16) |
C24 | 0.0256 (18) | 0.0238 (18) | 0.037 (2) | 0.0052 (15) | −0.0035 (15) | −0.0053 (15) |
C25 | 0.0253 (18) | 0.0208 (16) | 0.0255 (17) | 0.0042 (14) | 0.0008 (14) | −0.0062 (13) |
C26 | 0.0212 (17) | 0.035 (2) | 0.032 (2) | −0.0007 (15) | 0.0052 (15) | −0.0049 (16) |
C1 | 0.033 (2) | 0.0230 (18) | 0.034 (2) | 0.0041 (15) | 0.0144 (16) | 0.0036 (15) |
C2 | 0.0294 (18) | 0.0176 (15) | 0.0243 (17) | 0.0017 (14) | 0.0097 (14) | −0.0003 (13) |
C7 | 0.033 (2) | 0.0257 (18) | 0.0265 (18) | −0.0051 (15) | 0.0072 (15) | −0.0014 (14) |
C6 | 0.032 (2) | 0.034 (2) | 0.0277 (19) | 0.0006 (17) | 0.0032 (16) | 0.0013 (16) |
C3A—O3 | 1.304 (5) | C18—C19 | 1.523 (5) |
C3A—C2 | 1.389 (5) | C18—H18A | 0.9900 |
C3A—C4A | 1.405 (5) | C18—H18B | 0.9900 |
C4A—O4 | 1.324 (8) | C19—C20 | 1.523 (6) |
C4A—C5A | 1.375 (6) | C19—H19 | 1.0000 |
C5A—O5 | 1.362 (8) | C20—H20A | 0.9900 |
C5A—C6 | 1.391 (6) | C20—H20B | 0.9900 |
O3—H3 | 0.8400 | C21—C22 | 1.372 (6) |
O4—H4 | 0.8400 | C21—C30 | 1.429 (5) |
O5—H5 | 0.8400 | C30—C29 | 1.413 (5) |
C3B—C2 | 1.389 (5) | C30—C25 | 1.423 (5) |
C3B—C4B | 1.405 (5) | C29—C28 | 1.381 (5) |
C3B—H3B | 0.9500 | C29—H29 | 0.9500 |
C4B—C5B | 1.375 (6) | C28—C27 | 1.412 (5) |
C4B—H4B | 0.9500 | C28—H28 | 0.9500 |
C5B—C6 | 1.391 (6) | C27—C26 | 1.377 (6) |
C5B—H5B | 0.9500 | C27—H27 | 0.9500 |
O6—C9 | 1.368 (5) | C10—C11 | 1.392 (6) |
O6—C8 | 1.437 (4) | C10—H10 | 0.9500 |
O8—C21 | 1.362 (5) | C11—C12 | 1.383 (6) |
O8—C20 | 1.433 (4) | C11—H11 | 0.9500 |
O7—C19 | 1.414 (5) | C12—C13 | 1.396 (6) |
O7—H7 | 0.8400 | C12—H12 | 0.9500 |
O2—C1 | 1.257 (5) | C13—H13 | 0.9500 |
O1—C1 | 1.246 (5) | C16—C17 | 1.510 (5) |
N1—C31 | 1.426 (5) | C16—H16A | 0.9900 |
N1—C14 | 1.458 (4) | C16—H16B | 0.9900 |
N1—C17 | 1.472 (4) | C17—H17A | 0.9900 |
N2—C18 | 1.493 (5) | C17—H17B | 0.9900 |
N2—C16 | 1.493 (4) | C22—C23 | 1.409 (6) |
N2—C15 | 1.503 (4) | C22—H22 | 0.9500 |
N2—H2 | 1.0000 | C23—C24 | 1.365 (6) |
C8—H8A | 0.9800 | C23—H23 | 0.9500 |
C8—H8B | 0.9800 | C24—C25 | 1.423 (5) |
C8—H8C | 0.9800 | C24—H24 | 0.9500 |
C9—C10 | 1.388 (5) | C25—C26 | 1.421 (6) |
C9—C31 | 1.417 (5) | C26—H26 | 0.9500 |
C31—C13 | 1.390 (5) | C1—C2 | 1.509 (5) |
C14—C15 | 1.509 (6) | C2—C7 | 1.397 (6) |
C14—H14A | 0.9900 | C7—C6 | 1.390 (6) |
C14—H14B | 0.9900 | C7—H7A | 0.9500 |
C15—H15A | 0.9900 | C6—H6A | 0.9500 |
C15—H15B | 0.9900 | C6—H6B | 0.9500 |
O3—C3A—C2 | 123.3 (4) | C19—C20—H20B | 110.5 |
O3—C3A—C4A | 116.1 (4) | H20A—C20—H20B | 108.7 |
C2—C3A—C4A | 120.6 (4) | O8—C21—C22 | 125.5 (4) |
O4—C4A—C5A | 123.3 (5) | O8—C21—C30 | 113.4 (3) |
O4—C4A—C3A | 116.8 (5) | C22—C21—C30 | 121.0 (4) |
C5A—C4A—C3A | 119.9 (4) | C29—C30—C25 | 119.9 (3) |
O5—C5A—C4A | 129.6 (5) | C29—C30—C21 | 121.8 (3) |
O5—C5A—C6 | 109.8 (5) | C25—C30—C21 | 118.3 (3) |
C4A—C5A—C6 | 120.5 (4) | C28—C29—C30 | 120.3 (3) |
C3A—O3—H3 | 109.5 | C28—C29—H29 | 119.9 |
C4A—O4—H4 | 109.5 | C30—C29—H29 | 119.9 |
C5A—O5—H5 | 109.5 | C29—C28—C27 | 120.2 (4) |
C2—C3B—C4B | 120.6 (4) | C29—C28—H28 | 119.9 |
C2—C3B—H3B | 119.7 | C27—C28—H28 | 119.9 |
C4B—C3B—H3B | 119.7 | C26—C27—C28 | 120.5 (4) |
C5B—C4B—C3B | 119.9 (4) | C26—C27—H27 | 119.8 |
C5B—C4B—H4B | 120.1 | C28—C27—H27 | 119.8 |
C3B—C4B—H4B | 120.1 | C9—C10—C11 | 120.3 (3) |
C4B—C5B—C6 | 120.5 (4) | C9—C10—H10 | 119.8 |
C4B—C5B—H5B | 119.7 | C11—C10—H10 | 119.8 |
C6—C5B—H5B | 119.7 | C12—C11—C10 | 120.7 (4) |
C9—O6—C8 | 116.7 (3) | C12—C11—H11 | 119.6 |
C21—O8—C20 | 119.2 (3) | C10—C11—H11 | 119.6 |
C19—O7—H7 | 109.5 | C11—C12—C13 | 118.7 (4) |
C31—N1—C14 | 115.6 (3) | C11—C12—H12 | 120.6 |
C31—N1—C17 | 114.7 (3) | C13—C12—H12 | 120.6 |
C14—N1—C17 | 108.6 (3) | C31—C13—C12 | 122.1 (4) |
C18—N2—C16 | 111.8 (3) | C31—C13—H13 | 119.0 |
C18—N2—C15 | 109.1 (3) | C12—C13—H13 | 119.0 |
C16—N2—C15 | 111.3 (3) | N2—C16—C17 | 111.2 (3) |
C18—N2—H2 | 108.2 | N2—C16—H16A | 109.4 |
C16—N2—H2 | 108.2 | C17—C16—H16A | 109.4 |
C15—N2—H2 | 108.2 | N2—C16—H16B | 109.4 |
O6—C8—H8A | 109.5 | C17—C16—H16B | 109.4 |
O6—C8—H8B | 109.5 | H16A—C16—H16B | 108.0 |
H8A—C8—H8B | 109.5 | N1—C17—C16 | 110.3 (3) |
O6—C8—H8C | 109.5 | N1—C17—H17A | 109.6 |
H8A—C8—H8C | 109.5 | C16—C17—H17A | 109.6 |
H8B—C8—H8C | 109.5 | N1—C17—H17B | 109.6 |
O6—C9—C10 | 124.2 (3) | C16—C17—H17B | 109.6 |
O6—C9—C31 | 115.8 (3) | H17A—C17—H17B | 108.1 |
C10—C9—C31 | 120.0 (3) | C21—C22—C23 | 119.4 (4) |
C13—C31—C9 | 118.1 (4) | C21—C22—H22 | 120.3 |
C13—C31—N1 | 123.2 (3) | C23—C22—H22 | 120.3 |
C9—C31—N1 | 118.6 (3) | C24—C23—C22 | 121.6 (4) |
N1—C14—C15 | 109.4 (3) | C24—C23—H23 | 119.2 |
N1—C14—H14A | 109.8 | C22—C23—H23 | 119.2 |
C15—C14—H14A | 109.8 | C23—C24—C25 | 119.9 (4) |
N1—C14—H14B | 109.8 | C23—C24—H24 | 120.0 |
C15—C14—H14B | 109.8 | C25—C24—H24 | 120.0 |
H14A—C14—H14B | 108.2 | C26—C25—C30 | 118.5 (3) |
N2—C15—C14 | 111.5 (3) | C26—C25—C24 | 122.1 (4) |
N2—C15—H15A | 109.3 | C30—C25—C24 | 119.3 (4) |
C14—C15—H15A | 109.3 | C27—C26—C25 | 120.7 (4) |
N2—C15—H15B | 109.3 | C27—C26—H26 | 119.7 |
C14—C15—H15B | 109.3 | C25—C26—H26 | 119.7 |
H15A—C15—H15B | 108.0 | O1—C1—O2 | 124.1 (4) |
N2—C18—C19 | 113.9 (3) | O1—C1—C2 | 119.0 (4) |
N2—C18—H18A | 108.8 | O2—C1—C2 | 116.9 (4) |
C19—C18—H18A | 108.8 | C3B—C2—C7 | 118.3 (3) |
N2—C18—H18B | 108.8 | C3A—C2—C7 | 118.3 (3) |
C19—C18—H18B | 108.8 | C3B—C2—C1 | 120.8 (4) |
H18A—C18—H18B | 107.7 | C3A—C2—C1 | 120.8 (4) |
O7—C19—C20 | 112.6 (3) | C7—C2—C1 | 120.9 (3) |
O7—C19—C18 | 111.2 (3) | C6—C7—C2 | 121.5 (4) |
C20—C19—C18 | 109.7 (3) | C6—C7—H7A | 119.2 |
O7—C19—H19 | 107.7 | C2—C7—H7A | 119.2 |
C20—C19—H19 | 107.7 | C7—C6—C5A | 119.2 (4) |
C18—C19—H19 | 107.7 | C7—C6—C5B | 119.2 (4) |
O8—C20—C19 | 106.0 (3) | C7—C6—H6A | 120.4 |
O8—C20—H20A | 110.5 | C5A—C6—H6A | 120.4 |
C19—C20—H20A | 110.5 | C7—C6—H6B | 120.4 |
O8—C20—H20B | 110.5 | C5B—C6—H6B | 120.4 |
O3—C3A—C4A—O4 | 0.6 (7) | C9—C10—C11—C12 | 0.1 (6) |
C2—C3A—C4A—O4 | −179.2 (5) | C10—C11—C12—C13 | −0.1 (6) |
O3—C3A—C4A—C5A | −179.6 (4) | C9—C31—C13—C12 | 0.5 (6) |
C2—C3A—C4A—C5A | 0.6 (6) | N1—C31—C13—C12 | 177.0 (3) |
O4—C4A—C5A—O5 | −5.1 (9) | C11—C12—C13—C31 | −0.2 (6) |
C3A—C4A—C5A—O5 | 175.2 (5) | C18—N2—C16—C17 | −172.5 (3) |
O4—C4A—C5A—C6 | 179.7 (6) | C15—N2—C16—C17 | −50.2 (4) |
C3A—C4A—C5A—C6 | −0.1 (6) | C31—N1—C17—C16 | 165.6 (3) |
C2—C3B—C4B—C5B | 0.6 (6) | C14—N1—C17—C16 | −63.4 (4) |
C3B—C4B—C5B—C6 | −0.1 (6) | N2—C16—C17—N1 | 56.7 (4) |
C8—O6—C9—C10 | −2.7 (5) | O8—C21—C22—C23 | 176.6 (4) |
C8—O6—C9—C31 | 179.1 (3) | C30—C21—C22—C23 | −4.4 (6) |
O6—C9—C31—C13 | 177.8 (3) | C21—C22—C23—C24 | −0.9 (6) |
C10—C9—C31—C13 | −0.5 (5) | C22—C23—C24—C25 | 4.5 (6) |
O6—C9—C31—N1 | 1.1 (5) | C29—C30—C25—C26 | 0.0 (5) |
C10—C9—C31—N1 | −177.2 (3) | C21—C30—C25—C26 | −178.5 (3) |
C14—N1—C31—C13 | −13.2 (5) | C29—C30—C25—C24 | 176.2 (3) |
C17—N1—C31—C13 | 114.4 (4) | C21—C30—C25—C24 | −2.3 (5) |
C14—N1—C31—C9 | 163.3 (3) | C23—C24—C25—C26 | 173.3 (4) |
C17—N1—C31—C9 | −69.2 (4) | C23—C24—C25—C30 | −2.8 (5) |
C31—N1—C14—C15 | −165.8 (3) | C28—C27—C26—C25 | −1.5 (6) |
C17—N1—C14—C15 | 63.7 (4) | C30—C25—C26—C27 | 2.0 (6) |
C18—N2—C15—C14 | 175.1 (3) | C24—C25—C26—C27 | −174.2 (4) |
C16—N2—C15—C14 | 51.2 (4) | C4B—C3B—C2—C7 | −0.9 (5) |
N1—C14—C15—N2 | −58.2 (4) | C4B—C3B—C2—C1 | 176.8 (3) |
C16—N2—C18—C19 | −57.0 (4) | O3—C3A—C2—C7 | 179.3 (4) |
C15—N2—C18—C19 | 179.4 (3) | C4A—C3A—C2—C7 | −0.9 (5) |
N2—C18—C19—O7 | −49.9 (4) | O3—C3A—C2—C1 | −3.1 (6) |
N2—C18—C19—C20 | −175.2 (3) | C4A—C3A—C2—C1 | 176.8 (3) |
C21—O8—C20—C19 | −163.9 (3) | O1—C1—C2—C3B | −180.0 (4) |
O7—C19—C20—O8 | −58.5 (4) | O2—C1—C2—C3B | −1.6 (5) |
C18—C19—C20—O8 | 65.9 (4) | O1—C1—C2—C3A | −180.0 (4) |
C20—O8—C21—C22 | −9.6 (6) | O2—C1—C2—C3A | −1.6 (5) |
C20—O8—C21—C30 | 171.3 (3) | O1—C1—C2—C7 | −2.4 (5) |
O8—C21—C30—C29 | 6.6 (5) | O2—C1—C2—C7 | 176.0 (4) |
C22—C21—C30—C29 | −172.5 (3) | C3B—C2—C7—C6 | 0.7 (6) |
O8—C21—C30—C25 | −175.0 (3) | C3A—C2—C7—C6 | 0.7 (6) |
C22—C21—C30—C25 | 5.9 (5) | C1—C2—C7—C6 | −176.9 (4) |
C25—C30—C29—C28 | −2.4 (5) | C2—C7—C6—C5A | −0.2 (6) |
C21—C30—C29—C28 | 176.0 (3) | C2—C7—C6—C5B | −0.2 (6) |
C30—C29—C28—C27 | 3.0 (6) | O5—C5A—C6—C7 | −176.2 (5) |
C29—C28—C27—C26 | −1.0 (6) | C4A—C5A—C6—C7 | −0.1 (6) |
O6—C9—C10—C11 | −177.9 (3) | C4B—C5B—C6—C7 | −0.1 (6) |
C31—C9—C10—C11 | 0.2 (5) |
C31H34N2O6.40 | F(000) = 1141 |
Mr = 537.00 | Dx = 1.305 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.410 (4) Å | Cell parameters from 9941 reflections |
b = 17.772 (6) Å | θ = 2.5–29.0° |
c = 13.550 (5) Å | µ = 0.09 mm−1 |
β = 95.891 (19)° | T = 100 K |
V = 2733.1 (17) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.15 × 0.1 mm |
Bruker APEX-II CCD diffractometer | 4300 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.056 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0948 before and 0.0623 after correction. The Ratio of minimum to maximum transmission is 0.9102. The λ/2 correction factor is Not present. | θmax = 26.3°, θmin = 2.3° |
Tmin = 0.679, Tmax = 0.746 | h = −14→14 |
46089 measured reflections | k = −21→22 |
5487 independent reflections | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.075 | H-atom parameters constrained |
wR(F2) = 0.163 | w = 1/[σ2(Fo2) + (0.0212P)2 + 2.2798P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
5487 reflections | Δρmax = 0.16 e Å−3 |
375 parameters | Δρmin = −0.15 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C3A | −0.0546 (3) | 0.54545 (18) | 0.1022 (2) | 0.0771 (8) | 0.7 |
C4A | −0.0307 (4) | 0.47733 (18) | 0.1528 (2) | 0.0890 (11) | 0.36 |
C7A | 0.1480 (4) | 0.57706 (18) | 0.1333 (2) | 0.0801 (9) | 0.34 |
O3 | −0.1660 (3) | 0.5591 (2) | 0.0685 (3) | 0.1023 (11) | 0.7 |
H3 | −0.170803 | 0.600637 | 0.042123 | 0.153* | 0.7 |
O4 | −0.1095 (5) | 0.4325 (3) | 0.1584 (4) | 0.0831 (18) | 0.36 |
H4 | −0.086394 | 0.398425 | 0.196338 | 0.125* | 0.36 |
O5 | 0.2210 (6) | 0.6174 (5) | 0.1275 (7) | 0.118 (3) | 0.34 |
H7A | 0.197078 | 0.653205 | 0.092986 | 0.177* | 0.34 |
C3B | −0.0546 (3) | 0.54545 (18) | 0.1022 (2) | 0.0771 (8) | 0.3 |
H3B | −0.131043 | 0.556713 | 0.075901 | 0.093* | 0.3 |
C4B | −0.0307 (4) | 0.47733 (18) | 0.1528 (2) | 0.0890 (11) | 0.64 |
H4B | −0.091316 | 0.443236 | 0.159043 | 0.107* | 0.64 |
C7B | 0.1480 (4) | 0.57706 (18) | 0.1333 (2) | 0.0801 (9) | 0.66 |
H7B | 0.209875 | 0.610267 | 0.127256 | 0.096* | 0.66 |
O6 | −0.29386 (18) | −0.05835 (10) | 0.04871 (15) | 0.0730 (6) | |
O7 | 0.0544 (2) | 0.26782 (11) | 0.20294 (16) | 0.0892 (7) | |
H7 | 0.068999 | 0.290536 | 0.152958 | 0.134* | |
O8 | 0.2965 (2) | 0.25852 (12) | 0.19295 (16) | 0.0858 (7) | |
N1 | −0.18948 (19) | 0.05663 (11) | −0.03834 (15) | 0.0564 (5) | |
N2 | −0.00877 (19) | 0.15510 (10) | 0.05316 (15) | 0.0542 (5) | |
H2 | −0.038947 | 0.206131 | 0.039980 | 0.065* | |
C8 | −0.3447 (3) | −0.12019 (18) | 0.0967 (3) | 0.0914 (10) | |
H8A | −0.345575 | −0.163859 | 0.054952 | 0.137* | |
H8B | −0.423822 | −0.107765 | 0.108826 | 0.137* | |
H8C | −0.298738 | −0.130469 | 0.158641 | 0.137* | |
C9 | −0.3467 (2) | −0.03711 (14) | −0.0429 (2) | 0.0617 (7) | |
C15 | −0.1190 (2) | 0.10269 (15) | −0.09917 (19) | 0.0635 (7) | |
H15A | −0.158590 | 0.150186 | −0.114522 | 0.076* | |
H15B | −0.110059 | 0.076985 | −0.161109 | 0.076* | |
C16 | −0.0004 (2) | 0.11690 (15) | −0.04463 (18) | 0.0600 (7) | |
H16A | 0.045371 | 0.148106 | −0.085207 | 0.072* | |
H16B | 0.040714 | 0.069398 | −0.033396 | 0.072* | |
C19 | 0.1110 (3) | 0.16116 (14) | 0.1079 (2) | 0.0634 (7) | |
H19A | 0.161021 | 0.189178 | 0.067288 | 0.076* | |
H19B | 0.143785 | 0.110965 | 0.116801 | 0.076* | |
C20 | 0.1154 (3) | 0.19883 (15) | 0.2087 (2) | 0.0748 (8) | |
H20 | 0.075141 | 0.165570 | 0.252005 | 0.090* | |
C21 | 0.2404 (3) | 0.20705 (17) | 0.2540 (2) | 0.0876 (10) | |
H21A | 0.242377 | 0.226320 | 0.321084 | 0.105* | |
H21B | 0.280129 | 0.158751 | 0.256067 | 0.105* | |
C22 | 0.4168 (3) | 0.26369 (15) | 0.2028 (3) | 0.0805 (9) | |
C31 | 0.4629 (3) | 0.30818 (16) | 0.1289 (2) | 0.0750 (8) | |
C26 | 0.5881 (3) | 0.31281 (19) | 0.1283 (3) | 0.0883 (10) | |
C27 | 0.6331 (4) | 0.3581 (3) | 0.0560 (3) | 0.1048 (13) | |
H27 | 0.714144 | 0.360480 | 0.053458 | 0.126* | |
C28 | 0.5610 (4) | 0.3987 (3) | −0.0103 (3) | 0.1092 (13) | |
H28 | 0.593069 | 0.429494 | −0.055996 | 0.131* | |
C13 | −0.3406 (3) | 0.04479 (16) | −0.1825 (2) | 0.0711 (8) | |
H13 | −0.306019 | 0.084370 | −0.213836 | 0.085* | |
C11 | −0.4901 (3) | −0.04859 (19) | −0.1851 (3) | 0.0829 (9) | |
H11 | −0.556064 | −0.072297 | −0.216999 | 0.100* | |
C23 | 0.4889 (4) | 0.23073 (19) | 0.2767 (3) | 0.1122 (15) | |
H23 | 0.457359 | 0.204518 | 0.327204 | 0.135* | |
C24 | 0.6122 (5) | 0.2369 (2) | 0.2756 (5) | 0.134 (2) | |
H24 | 0.661563 | 0.214539 | 0.326101 | 0.161* | |
C25 | 0.6604 (4) | 0.2746 (2) | 0.2030 (4) | 0.1177 (16) | |
H25 | 0.741773 | 0.275315 | 0.202327 | 0.141* | |
C30 | 0.3914 (3) | 0.34907 (19) | 0.0577 (2) | 0.0801 (9) | |
H30 | 0.309950 | 0.345603 | 0.056127 | 0.096* | |
C29 | 0.4393 (3) | 0.3940 (2) | −0.0097 (3) | 0.0994 (12) | |
H29 | 0.390285 | 0.421604 | −0.055370 | 0.119* | |
C14 | −0.2929 (2) | 0.02305 (14) | −0.08851 (19) | 0.0568 (6) | |
C18 | −0.2088 (3) | 0.09937 (15) | 0.0516 (2) | 0.0642 (7) | |
H18A | −0.259773 | 0.070975 | 0.090976 | 0.077* | |
H18B | −0.247390 | 0.146693 | 0.033110 | 0.077* | |
C17 | −0.0933 (3) | 0.11434 (14) | 0.11167 (19) | 0.0626 (7) | |
H17A | −0.107067 | 0.144136 | 0.169352 | 0.075* | |
H17B | −0.058648 | 0.066903 | 0.134911 | 0.075* | |
C12 | −0.4380 (3) | 0.00939 (18) | −0.2310 (2) | 0.0810 (9) | |
H12 | −0.467922 | 0.024795 | −0.294235 | 0.097* | |
C10 | −0.4448 (3) | −0.07207 (16) | −0.0913 (2) | 0.0735 (8) | |
H10 | −0.480490 | −0.111546 | −0.060686 | 0.088* | |
O1 | 0.0950 (2) | 0.71188 (12) | 0.02539 (18) | 0.0895 (7) | |
O2 | −0.0908 (2) | 0.67884 (14) | −0.0053 (2) | 0.1036 (8) | |
C5 | 0.0812 (4) | 0.46090 (18) | 0.1927 (2) | 0.0893 (11) | |
H5A | 0.096451 | 0.415731 | 0.226295 | 0.107* | 0.36 |
H5B | 0.096451 | 0.415731 | 0.226295 | 0.107* | 0.64 |
C2 | 0.0354 (3) | 0.59562 (14) | 0.09159 (19) | 0.0646 (7) | |
C1 | 0.0127 (3) | 0.66747 (17) | 0.0338 (2) | 0.0764 (9) | |
C6 | 0.1697 (4) | 0.50999 (19) | 0.1837 (2) | 0.0887 (10) | |
H6A | 0.245566 | 0.498687 | 0.211519 | 0.106* | 0.34 |
H6B | 0.245566 | 0.498687 | 0.211519 | 0.106* | 0.66 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C3A | 0.109 (3) | 0.0700 (19) | 0.0516 (15) | 0.0057 (18) | 0.0058 (16) | 0.0037 (14) |
C4A | 0.151 (3) | 0.0626 (18) | 0.0538 (17) | −0.021 (2) | 0.010 (2) | 0.0001 (14) |
C7A | 0.109 (3) | 0.0671 (19) | 0.0648 (18) | 0.0176 (19) | 0.0132 (18) | 0.0000 (15) |
O3 | 0.108 (3) | 0.107 (3) | 0.090 (2) | −0.006 (2) | 0.000 (2) | 0.035 (2) |
O4 | 0.098 (4) | 0.079 (4) | 0.071 (4) | −0.044 (3) | −0.004 (3) | 0.023 (3) |
O5 | 0.069 (4) | 0.119 (7) | 0.167 (8) | −0.034 (4) | 0.010 (5) | 0.049 (6) |
C3B | 0.109 (3) | 0.0700 (19) | 0.0516 (15) | 0.0057 (18) | 0.0058 (16) | 0.0037 (14) |
C4B | 0.151 (3) | 0.0626 (18) | 0.0538 (17) | −0.021 (2) | 0.010 (2) | 0.0001 (14) |
C7B | 0.109 (3) | 0.0671 (19) | 0.0648 (18) | 0.0176 (19) | 0.0132 (18) | 0.0000 (15) |
O6 | 0.0822 (13) | 0.0623 (11) | 0.0750 (13) | −0.0164 (10) | 0.0105 (10) | 0.0157 (10) |
O7 | 0.134 (2) | 0.0583 (12) | 0.0768 (14) | −0.0031 (13) | 0.0172 (13) | −0.0079 (10) |
O8 | 0.0963 (16) | 0.0703 (13) | 0.0865 (15) | −0.0183 (12) | −0.0119 (12) | 0.0172 (11) |
N1 | 0.0696 (13) | 0.0495 (11) | 0.0516 (11) | −0.0094 (10) | 0.0144 (10) | 0.0008 (9) |
N2 | 0.0727 (14) | 0.0352 (9) | 0.0567 (12) | −0.0052 (9) | 0.0159 (10) | 0.0002 (8) |
C8 | 0.117 (3) | 0.0706 (19) | 0.089 (2) | −0.0212 (19) | 0.022 (2) | 0.0197 (17) |
C9 | 0.0680 (17) | 0.0512 (14) | 0.0669 (16) | −0.0016 (12) | 0.0117 (13) | 0.0009 (12) |
C15 | 0.0778 (18) | 0.0629 (16) | 0.0519 (14) | −0.0109 (13) | 0.0159 (13) | 0.0032 (12) |
C16 | 0.0727 (17) | 0.0530 (14) | 0.0572 (15) | −0.0077 (12) | 0.0209 (13) | −0.0030 (11) |
C19 | 0.0764 (18) | 0.0441 (13) | 0.0696 (17) | −0.0053 (12) | 0.0072 (14) | 0.0010 (12) |
C20 | 0.109 (2) | 0.0497 (15) | 0.0654 (17) | −0.0165 (15) | 0.0070 (16) | 0.0077 (13) |
C21 | 0.122 (3) | 0.0603 (17) | 0.076 (2) | −0.0222 (18) | −0.0123 (19) | 0.0116 (15) |
C22 | 0.092 (2) | 0.0455 (15) | 0.097 (2) | −0.0067 (15) | −0.0211 (19) | −0.0091 (15) |
C31 | 0.083 (2) | 0.0584 (16) | 0.081 (2) | −0.0061 (15) | −0.0045 (16) | −0.0258 (15) |
C26 | 0.084 (2) | 0.072 (2) | 0.105 (3) | 0.0022 (18) | −0.006 (2) | −0.043 (2) |
C27 | 0.080 (2) | 0.127 (3) | 0.109 (3) | −0.015 (2) | 0.019 (2) | −0.050 (3) |
C28 | 0.094 (3) | 0.150 (4) | 0.085 (3) | −0.020 (3) | 0.019 (2) | −0.016 (3) |
C13 | 0.083 (2) | 0.0615 (16) | 0.0680 (17) | −0.0031 (14) | 0.0039 (15) | 0.0062 (14) |
C11 | 0.078 (2) | 0.074 (2) | 0.094 (2) | −0.0034 (16) | −0.0065 (18) | −0.0143 (18) |
C23 | 0.129 (3) | 0.0565 (19) | 0.139 (3) | −0.010 (2) | −0.044 (3) | 0.012 (2) |
C24 | 0.128 (4) | 0.060 (2) | 0.197 (5) | 0.009 (2) | −0.063 (4) | 0.003 (3) |
C25 | 0.097 (3) | 0.069 (2) | 0.179 (5) | 0.010 (2) | −0.026 (3) | −0.038 (3) |
C30 | 0.078 (2) | 0.094 (2) | 0.0674 (18) | −0.0106 (18) | 0.0022 (16) | −0.0057 (17) |
C29 | 0.090 (3) | 0.135 (3) | 0.073 (2) | −0.019 (2) | 0.0094 (18) | 0.001 (2) |
C14 | 0.0626 (15) | 0.0481 (13) | 0.0609 (15) | −0.0029 (11) | 0.0124 (12) | −0.0001 (11) |
C18 | 0.0775 (18) | 0.0547 (14) | 0.0637 (16) | −0.0092 (13) | 0.0229 (14) | −0.0035 (12) |
C17 | 0.0867 (19) | 0.0497 (13) | 0.0542 (14) | −0.0132 (13) | 0.0213 (13) | −0.0004 (11) |
C12 | 0.084 (2) | 0.079 (2) | 0.076 (2) | −0.0020 (17) | −0.0063 (16) | −0.0022 (17) |
C10 | 0.0702 (18) | 0.0582 (16) | 0.093 (2) | −0.0115 (14) | 0.0138 (16) | −0.0026 (15) |
O1 | 0.1040 (17) | 0.0571 (12) | 0.1101 (18) | 0.0002 (12) | 0.0236 (14) | 0.0168 (12) |
O2 | 0.1003 (18) | 0.0855 (16) | 0.124 (2) | 0.0128 (14) | 0.0086 (15) | 0.0417 (15) |
C5 | 0.154 (4) | 0.0563 (17) | 0.0543 (17) | 0.020 (2) | −0.004 (2) | 0.0010 (14) |
C2 | 0.097 (2) | 0.0471 (13) | 0.0524 (14) | 0.0080 (14) | 0.0203 (14) | −0.0005 (11) |
C1 | 0.105 (3) | 0.0604 (17) | 0.0668 (18) | 0.0192 (18) | 0.0240 (18) | 0.0062 (14) |
C6 | 0.121 (3) | 0.072 (2) | 0.073 (2) | 0.020 (2) | 0.0078 (19) | 0.0056 (16) |
C3A—O3 | 1.328 (4) | C19—H19B | 0.9700 |
C3A—C2 | 1.378 (4) | C20—C21 | 1.500 (4) |
C3A—C4A | 1.404 (4) | C20—H20 | 0.9800 |
C4A—O4 | 1.209 (6) | C21—H21A | 0.9700 |
C4A—C5 | 1.367 (5) | C21—H21B | 0.9700 |
C7A—O5 | 1.108 (7) | C22—C23 | 1.361 (5) |
C7A—C6 | 1.383 (4) | C22—C31 | 1.418 (5) |
C7A—C2 | 1.390 (4) | C31—C30 | 1.401 (4) |
O3—H3 | 0.8200 | C31—C26 | 1.432 (5) |
O4—H4 | 0.8200 | C26—C27 | 1.405 (6) |
O5—H7A | 0.8200 | C26—C25 | 1.413 (6) |
C3B—C2 | 1.378 (4) | C27—C28 | 1.360 (6) |
C3B—C4B | 1.404 (4) | C27—H27 | 0.9300 |
C3B—H3B | 0.9300 | C28—C29 | 1.392 (5) |
C4B—C5 | 1.367 (5) | C28—H28 | 0.9300 |
C4B—H4B | 0.9300 | C13—C12 | 1.383 (4) |
C7B—C6 | 1.383 (4) | C13—C14 | 1.388 (4) |
C7B—C2 | 1.390 (4) | C13—H13 | 0.9300 |
C7B—H7B | 0.9300 | C11—C12 | 1.370 (4) |
O6—C9 | 1.376 (3) | C11—C10 | 1.386 (4) |
O6—C8 | 1.430 (3) | C11—H11 | 0.9300 |
O7—C20 | 1.408 (4) | C23—C24 | 1.414 (6) |
O7—H7 | 0.8200 | C23—H23 | 0.9300 |
O8—C22 | 1.369 (4) | C24—C25 | 1.351 (7) |
O8—C21 | 1.428 (4) | C24—H24 | 0.9300 |
N1—C14 | 1.430 (3) | C25—H25 | 0.9300 |
N1—C15 | 1.460 (3) | C30—C29 | 1.368 (5) |
N1—C18 | 1.472 (3) | C30—H30 | 0.9300 |
N2—C19 | 1.491 (3) | C29—H29 | 0.9300 |
N2—C17 | 1.497 (3) | C18—C17 | 1.500 (4) |
N2—C16 | 1.501 (3) | C18—H18A | 0.9700 |
N2—H2 | 0.9800 | C18—H18B | 0.9700 |
C8—H8A | 0.9600 | C17—H17A | 0.9700 |
C8—H8B | 0.9600 | C17—H17B | 0.9700 |
C8—H8C | 0.9600 | C12—H12 | 0.9300 |
C9—C10 | 1.385 (4) | C10—H10 | 0.9300 |
C9—C14 | 1.407 (3) | O1—C1 | 1.241 (4) |
C15—C16 | 1.495 (4) | O2—C1 | 1.260 (4) |
C15—H15A | 0.9700 | C5—C6 | 1.349 (5) |
C15—H15B | 0.9700 | C5—H5A | 0.9300 |
C16—H16A | 0.9700 | C5—H5B | 0.9300 |
C16—H16B | 0.9700 | C2—C1 | 1.506 (4) |
C19—C20 | 1.517 (4) | C6—H6A | 0.9300 |
C19—H19A | 0.9700 | C6—H6B | 0.9300 |
O3—C3A—C2 | 122.9 (3) | C30—C31—C22 | 123.0 (3) |
O3—C3A—C4A | 117.1 (4) | C30—C31—C26 | 118.5 (3) |
C2—C3A—C4A | 120.0 (3) | C22—C31—C26 | 118.6 (3) |
O4—C4A—C5 | 120.3 (4) | C27—C26—C25 | 123.2 (4) |
O4—C4A—C3A | 119.4 (5) | C27—C26—C31 | 118.2 (4) |
C5—C4A—C3A | 120.3 (3) | C25—C26—C31 | 118.5 (4) |
O5—C7A—C6 | 119.7 (6) | C28—C27—C26 | 121.6 (4) |
O5—C7A—C2 | 119.2 (5) | C28—C27—H27 | 119.2 |
C6—C7A—C2 | 121.1 (4) | C26—C27—H27 | 119.2 |
C3A—O3—H3 | 109.5 | C27—C28—C29 | 120.1 (4) |
C4A—O4—H4 | 109.5 | C27—C28—H28 | 120.0 |
C7A—O5—H7A | 109.5 | C29—C28—H28 | 120.0 |
C2—C3B—C4B | 120.0 (3) | C12—C13—C14 | 122.0 (3) |
C2—C3B—H3B | 120.0 | C12—C13—H13 | 119.0 |
C4B—C3B—H3B | 120.0 | C14—C13—H13 | 119.0 |
C5—C4B—C3B | 120.3 (3) | C12—C11—C10 | 120.3 (3) |
C5—C4B—H4B | 119.9 | C12—C11—H11 | 119.8 |
C3B—C4B—H4B | 119.9 | C10—C11—H11 | 119.8 |
C6—C7B—C2 | 121.1 (4) | C22—C23—C24 | 119.0 (4) |
C6—C7B—H7B | 119.5 | C22—C23—H23 | 120.5 |
C2—C7B—H7B | 119.5 | C24—C23—H23 | 120.5 |
C9—O6—C8 | 117.4 (2) | C25—C24—C23 | 121.7 (4) |
C20—O7—H7 | 109.5 | C25—C24—H24 | 119.1 |
C22—O8—C21 | 119.4 (3) | C23—C24—H24 | 119.1 |
C14—N1—C15 | 116.2 (2) | C24—C25—C26 | 120.6 (4) |
C14—N1—C18 | 115.0 (2) | C24—C25—H25 | 119.7 |
C15—N1—C18 | 108.44 (19) | C26—C25—H25 | 119.7 |
C19—N2—C17 | 112.3 (2) | C29—C30—C31 | 121.2 (3) |
C19—N2—C16 | 109.5 (2) | C29—C30—H30 | 119.4 |
C17—N2—C16 | 110.60 (18) | C31—C30—H30 | 119.4 |
C19—N2—H2 | 108.1 | C30—C29—C28 | 120.3 (4) |
C17—N2—H2 | 108.1 | C30—C29—H29 | 119.8 |
C16—N2—H2 | 108.1 | C28—C29—H29 | 119.8 |
O6—C8—H8A | 109.5 | C13—C14—C9 | 117.8 (2) |
O6—C8—H8B | 109.5 | C13—C14—N1 | 123.1 (2) |
H8A—C8—H8B | 109.5 | C9—C14—N1 | 119.0 (2) |
O6—C8—H8C | 109.5 | N1—C18—C17 | 110.0 (2) |
H8A—C8—H8C | 109.5 | N1—C18—H18A | 109.7 |
H8B—C8—H8C | 109.5 | C17—C18—H18A | 109.7 |
O6—C9—C10 | 124.2 (2) | N1—C18—H18B | 109.7 |
O6—C9—C14 | 115.7 (2) | C17—C18—H18B | 109.7 |
C10—C9—C14 | 120.1 (3) | H18A—C18—H18B | 108.2 |
N1—C15—C16 | 109.8 (2) | N2—C17—C18 | 112.1 (2) |
N1—C15—H15A | 109.7 | N2—C17—H17A | 109.2 |
C16—C15—H15A | 109.7 | C18—C17—H17A | 109.2 |
N1—C15—H15B | 109.7 | N2—C17—H17B | 109.2 |
C16—C15—H15B | 109.7 | C18—C17—H17B | 109.2 |
H15A—C15—H15B | 108.2 | H17A—C17—H17B | 107.9 |
C15—C16—N2 | 112.1 (2) | C11—C12—C13 | 119.4 (3) |
C15—C16—H16A | 109.2 | C11—C12—H12 | 120.3 |
N2—C16—H16A | 109.2 | C13—C12—H12 | 120.3 |
C15—C16—H16B | 109.2 | C9—C10—C11 | 120.4 (3) |
N2—C16—H16B | 109.2 | C9—C10—H10 | 119.8 |
H16A—C16—H16B | 107.9 | C11—C10—H10 | 119.8 |
N2—C19—C20 | 115.1 (2) | C6—C5—C4A | 120.2 (3) |
N2—C19—H19A | 108.5 | C6—C5—C4B | 120.2 (3) |
C20—C19—H19A | 108.5 | C6—C5—H5A | 119.9 |
N2—C19—H19B | 108.5 | C4A—C5—H5A | 119.9 |
C20—C19—H19B | 108.5 | C6—C5—H5B | 119.9 |
H19A—C19—H19B | 107.5 | C4B—C5—H5B | 119.9 |
O7—C20—C21 | 112.4 (2) | C3B—C2—C7B | 118.1 (3) |
O7—C20—C19 | 111.3 (2) | C3A—C2—C7A | 118.1 (3) |
C21—C20—C19 | 110.7 (3) | C3B—C2—C1 | 120.9 (3) |
O7—C20—H20 | 107.4 | C3A—C2—C1 | 120.9 (3) |
C21—C20—H20 | 107.4 | C7B—C2—C1 | 121.0 (3) |
C19—C20—H20 | 107.4 | C7A—C2—C1 | 121.0 (3) |
O8—C21—C20 | 106.8 (2) | O1—C1—O2 | 123.0 (3) |
O8—C21—H21A | 110.4 | O1—C1—C2 | 119.7 (3) |
C20—C21—H21A | 110.4 | O2—C1—C2 | 117.3 (3) |
O8—C21—H21B | 110.4 | C5—C6—C7A | 120.3 (4) |
C20—C21—H21B | 110.4 | C5—C6—C7B | 120.3 (4) |
H21A—C21—H21B | 108.6 | C5—C6—H6A | 119.8 |
C23—C22—O8 | 124.5 (4) | C7A—C6—H6A | 119.8 |
C23—C22—C31 | 121.3 (4) | C5—C6—H6B | 119.8 |
O8—C22—C31 | 114.2 (3) | C7B—C6—H6B | 119.8 |
O3—C3A—C4A—O4 | 4.4 (6) | C10—C9—C14—C13 | −0.7 (4) |
C2—C3A—C4A—O4 | −177.2 (4) | O6—C9—C14—N1 | 0.5 (3) |
O3—C3A—C4A—C5 | −177.5 (3) | C10—C9—C14—N1 | −178.0 (2) |
C2—C3A—C4A—C5 | 0.9 (5) | C15—N1—C14—C13 | −14.3 (4) |
C2—C3B—C4B—C5 | 0.9 (5) | C18—N1—C14—C13 | 113.9 (3) |
C8—O6—C9—C10 | −0.5 (4) | C15—N1—C14—C9 | 162.9 (2) |
C8—O6—C9—C14 | −178.9 (3) | C18—N1—C14—C9 | −68.9 (3) |
C14—N1—C15—C16 | −165.2 (2) | C14—N1—C18—C17 | 165.2 (2) |
C18—N1—C15—C16 | 63.5 (3) | C15—N1—C18—C17 | −62.9 (3) |
N1—C15—C16—N2 | −58.1 (3) | C19—N2—C17—C18 | −172.4 (2) |
C19—N2—C16—C15 | 174.7 (2) | C16—N2—C17—C18 | −49.8 (3) |
C17—N2—C16—C15 | 50.5 (3) | N1—C18—C17—N2 | 56.7 (3) |
C17—N2—C19—C20 | −56.7 (3) | C10—C11—C12—C13 | −0.7 (5) |
C16—N2—C19—C20 | −179.9 (2) | C14—C13—C12—C11 | 0.5 (5) |
N2—C19—C20—O7 | −50.1 (3) | O6—C9—C10—C11 | −177.8 (3) |
N2—C19—C20—C21 | −175.9 (2) | C14—C9—C10—C11 | 0.5 (4) |
C22—O8—C21—C20 | −165.1 (3) | C12—C11—C10—C9 | 0.2 (5) |
O7—C20—C21—O8 | −59.3 (3) | O4—C4A—C5—C6 | 177.9 (5) |
C19—C20—C21—O8 | 65.9 (3) | C3A—C4A—C5—C6 | −0.2 (5) |
C21—O8—C22—C23 | −9.7 (5) | C3B—C4B—C5—C6 | −0.2 (5) |
C21—O8—C22—C31 | 171.2 (3) | C4B—C3B—C2—C7B | −0.9 (4) |
C23—C22—C31—C30 | −173.4 (3) | C4B—C3B—C2—C1 | 177.3 (3) |
O8—C22—C31—C30 | 5.7 (4) | O3—C3A—C2—C7A | 177.3 (3) |
C23—C22—C31—C26 | 5.2 (4) | C4A—C3A—C2—C7A | −0.9 (4) |
O8—C22—C31—C26 | −175.6 (2) | O3—C3A—C2—C1 | −4.4 (5) |
C30—C31—C26—C27 | −0.1 (4) | C4A—C3A—C2—C1 | 177.3 (3) |
C22—C31—C26—C27 | −178.8 (3) | C6—C7B—C2—C3B | 0.3 (4) |
C30—C31—C26—C25 | 176.9 (3) | C6—C7B—C2—C1 | −178.0 (3) |
C22—C31—C26—C25 | −1.8 (4) | O5—C7A—C2—C3A | −178.2 (7) |
C25—C26—C27—C28 | −175.0 (4) | C6—C7A—C2—C3A | 0.3 (4) |
C31—C26—C27—C28 | 1.9 (5) | O5—C7A—C2—C1 | 3.6 (8) |
C26—C27—C28—C29 | −2.1 (6) | C6—C7A—C2—C1 | −178.0 (3) |
O8—C22—C23—C24 | 176.6 (3) | C3B—C2—C1—O1 | 179.9 (3) |
C31—C22—C23—C24 | −4.3 (5) | C3A—C2—C1—O1 | 179.9 (3) |
C22—C23—C24—C25 | −0.1 (6) | C7B—C2—C1—O1 | −1.9 (4) |
C23—C24—C25—C26 | 3.6 (6) | C7A—C2—C1—O1 | −1.9 (4) |
C27—C26—C25—C24 | 174.4 (4) | C3B—C2—C1—O2 | −1.1 (4) |
C31—C26—C25—C24 | −2.5 (5) | C3A—C2—C1—O2 | −1.1 (4) |
C22—C31—C30—C29 | 177.1 (3) | C7B—C2—C1—O2 | 177.1 (3) |
C26—C31—C30—C29 | −1.6 (5) | C7A—C2—C1—O2 | 177.1 (3) |
C31—C30—C29—C28 | 1.5 (6) | C4A—C5—C6—C7A | −0.5 (5) |
C27—C28—C29—C30 | 0.3 (6) | C4B—C5—C6—C7B | −0.5 (5) |
C12—C13—C14—C9 | 0.2 (4) | O5—C7A—C6—C5 | 178.9 (7) |
C12—C13—C14—N1 | 177.4 (3) | C2—C7A—C6—C5 | 0.4 (5) |
O6—C9—C14—C13 | 177.8 (2) | C2—C7B—C6—C5 | 0.4 (5) |
C31H34N2O6.81 | F(000) = 1154 |
Mr = 543.56 | Dx = 1.326 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.405 Å | Cell parameters from 9890 reflections |
b = 17.746 Å | θ = 2.3–28.6° |
c = 13.511 Å | µ = 0.09 mm−1 |
β = 95.49° | T = 293 K |
V = 2722.0 Å3 | Block, colourless |
Z = 4 | 0.15 × 0.15 × 0.1 mm |
Bruker APEX-II CCD diffractometer | Rint = 0.057 |
φ and ω scans | θmax = 30.4°, θmin = 2.3° |
69144 measured reflections | h = −16→16 |
8182 independent reflections | k = −25→25 |
5170 reflections with I > 2σ(I) | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.081 | H-atom parameters constrained |
wR(F2) = 0.225 | w = 1/[σ2(Fo2) + (0.0757P)2 + 1.4079P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
8182 reflections | Δρmax = 0.28 e Å−3 |
375 parameters | Δρmin = −0.32 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C4A | 0.4775 (3) | 1.02310 (16) | 0.6559 (2) | 0.0694 (8) | 0.43 |
C7A | 0.6531 (3) | 0.92199 (16) | 0.6330 (2) | 0.0668 (7) | 0.38 |
O4 | 0.3936 (5) | 1.0689 (3) | 0.6593 (4) | 0.0926 (17) | 0.43 |
H4 | 0.340108 | 1.057462 | 0.617066 | 0.139* | 0.43 |
O5 | 0.7209 (8) | 0.8799 (6) | 0.6290 (10) | 0.158 (4) | 0.38 |
H7A | 0.693954 | 0.843869 | 0.596367 | 0.237* | 0.38 |
C4B | 0.4775 (3) | 1.02310 (16) | 0.6559 (2) | 0.0694 (8) | 0.57 |
H4B | 0.417844 | 1.057796 | 0.663222 | 0.083* | 0.57 |
C7B | 0.6531 (3) | 0.92199 (16) | 0.6330 (2) | 0.0668 (7) | 0.62 |
H7B | 0.714074 | 0.888288 | 0.625472 | 0.080* | 0.62 |
O8 | 0.20377 (19) | 0.75830 (11) | 0.30663 (15) | 0.0739 (6) | |
O6 | 0.79438 (16) | 0.44172 (10) | 0.45029 (14) | 0.0631 (5) | |
O7 | 0.4464 (2) | 0.76864 (10) | 0.29722 (15) | 0.0746 (6) | |
H7 | 0.429695 | 0.791444 | 0.346762 | 0.112* | |
O1 | 0.59746 (19) | 0.78748 (10) | 0.52515 (17) | 0.0770 (6) | |
O2 | 0.4111 (2) | 0.82161 (12) | 0.49643 (18) | 0.0812 (6) | |
N2 | 0.50856 (17) | 0.65513 (9) | 0.44633 (13) | 0.0460 (4) | |
H2 | 0.538432 | 0.706271 | 0.459666 | 0.055* | |
N1 | 0.68878 (17) | 0.55634 (10) | 0.53781 (14) | 0.0477 (4) | |
C28 | −0.0637 (3) | 0.8996 (2) | 0.5086 (3) | 0.0849 (10) | |
H28 | −0.096229 | 0.930609 | 0.554251 | 0.102* | |
C29 | 0.0591 (3) | 0.8948 (2) | 0.5081 (2) | 0.0781 (9) | |
H29 | 0.107903 | 0.922632 | 0.553591 | 0.094* | |
O3 | 0.3393 (2) | 0.94200 (15) | 0.57011 (19) | 0.0893 (7) | |
H3 | 0.333376 | 0.899439 | 0.546519 | 0.134* | |
C30 | 0.1070 (3) | 0.84972 (17) | 0.4413 (2) | 0.0654 (7) | |
H30 | 0.188479 | 0.846224 | 0.442958 | 0.078* | |
C31 | 0.0363 (2) | 0.80810 (14) | 0.3695 (2) | 0.0610 (6) | |
C22 | 0.0838 (3) | 0.76324 (14) | 0.2957 (2) | 0.0654 (7) | |
C21 | 0.2608 (3) | 0.70712 (16) | 0.2449 (2) | 0.0742 (8) | |
H21A | 0.259012 | 0.726609 | 0.177673 | 0.089* | |
H21B | 0.221767 | 0.658513 | 0.242659 | 0.089* | |
C20 | 0.3866 (3) | 0.69961 (14) | 0.29069 (19) | 0.0623 (7) | |
H20 | 0.427955 | 0.666670 | 0.247336 | 0.075* | |
C19 | 0.3892 (2) | 0.66119 (13) | 0.39186 (19) | 0.0539 (6) | |
H19A | 0.338738 | 0.689093 | 0.432686 | 0.065* | |
H19B | 0.356500 | 0.610943 | 0.382493 | 0.065* | |
C16 | 0.4992 (2) | 0.61686 (13) | 0.54438 (17) | 0.0518 (5) | |
H16A | 0.453509 | 0.648262 | 0.585143 | 0.062* | |
H16B | 0.457795 | 0.569444 | 0.533104 | 0.062* | |
C15 | 0.6177 (2) | 0.60211 (14) | 0.59906 (18) | 0.0555 (6) | |
H15A | 0.657284 | 0.649552 | 0.615033 | 0.067* | |
H15B | 0.608035 | 0.575998 | 0.660834 | 0.067* | |
C14 | 0.7918 (2) | 0.52258 (12) | 0.58829 (18) | 0.0489 (5) | |
C9 | 0.8463 (2) | 0.46252 (13) | 0.54186 (19) | 0.0517 (5) | |
C8 | 0.8462 (3) | 0.38018 (17) | 0.4018 (3) | 0.0803 (9) | |
H8A | 0.802403 | 0.371010 | 0.338702 | 0.120* | |
H8B | 0.844806 | 0.335866 | 0.442439 | 0.120* | |
H8C | 0.926229 | 0.392340 | 0.391743 | 0.120* | |
C27 | −0.1348 (3) | 0.8589 (2) | 0.4426 (3) | 0.0845 (10) | |
H27 | −0.215953 | 0.861349 | 0.445091 | 0.101* | |
C26 | −0.0889 (3) | 0.81273 (16) | 0.3700 (2) | 0.0707 (8) | |
C25 | −0.1602 (3) | 0.77444 (19) | 0.2945 (3) | 0.0924 (12) | |
H25 | −0.241701 | 0.774991 | 0.294981 | 0.111* | |
C24 | −0.1109 (4) | 0.73702 (19) | 0.2215 (4) | 0.1030 (14) | |
H24 | −0.159609 | 0.715088 | 0.170262 | 0.124* | |
C23 | 0.0125 (3) | 0.73047 (16) | 0.2211 (3) | 0.0893 (11) | |
H23 | 0.044639 | 0.704129 | 0.170728 | 0.107* | |
C13 | 0.8380 (3) | 0.54394 (15) | 0.6826 (2) | 0.0626 (6) | |
H13 | 0.802694 | 0.583273 | 0.714196 | 0.075* | |
C12 | 0.9355 (3) | 0.50831 (17) | 0.7313 (2) | 0.0720 (8) | |
H12 | 0.964906 | 0.523669 | 0.794715 | 0.086* | |
C11 | 0.9878 (3) | 0.45058 (17) | 0.6853 (2) | 0.0717 (8) | |
H11 | 1.053117 | 0.426530 | 0.717572 | 0.086* | |
C10 | 0.9441 (2) | 0.42741 (14) | 0.5905 (2) | 0.0634 (7) | |
H10 | 0.980601 | 0.388217 | 0.559599 | 0.076* | |
C18 | 0.7093 (2) | 0.59949 (13) | 0.44819 (18) | 0.0533 (6) | |
H18A | 0.760982 | 0.571320 | 0.408813 | 0.064* | |
H18B | 0.747340 | 0.646892 | 0.467185 | 0.064* | |
C17 | 0.5944 (2) | 0.61446 (13) | 0.38748 (17) | 0.0514 (5) | |
H17A | 0.560104 | 0.566979 | 0.363831 | 0.062* | |
H17B | 0.608800 | 0.644517 | 0.329915 | 0.062* | |
C5 | 0.5885 (3) | 1.03861 (16) | 0.6939 (2) | 0.0737 (9) | |
H5A | 0.604512 | 1.083788 | 0.727417 | 0.088* | 0.43 |
H5B | 0.604512 | 1.083788 | 0.727417 | 0.088* | 0.57 |
C3 | 0.4508 (3) | 0.95470 (15) | 0.60501 (18) | 0.0600 (6) | |
C2 | 0.5406 (2) | 0.90401 (12) | 0.59316 (17) | 0.0531 (6) | |
C1 | 0.5153 (3) | 0.83232 (14) | 0.5344 (2) | 0.0626 (7) | |
C6 | 0.6778 (3) | 0.98868 (17) | 0.6838 (2) | 0.0734 (8) | |
H6A | 0.754152 | 0.999379 | 0.710712 | 0.088* | 0.38 |
H6B | 0.754152 | 0.999379 | 0.710712 | 0.088* | 0.62 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C4A | 0.106 (2) | 0.0548 (14) | 0.0470 (13) | 0.0161 (15) | 0.0076 (14) | −0.0008 (11) |
C7A | 0.090 (2) | 0.0540 (14) | 0.0571 (15) | −0.0117 (14) | 0.0107 (14) | 0.0002 (12) |
O4 | 0.099 (4) | 0.094 (4) | 0.083 (4) | 0.041 (3) | −0.007 (3) | −0.020 (3) |
O5 | 0.106 (6) | 0.139 (8) | 0.229 (12) | 0.039 (6) | 0.015 (7) | −0.059 (8) |
C4B | 0.106 (2) | 0.0548 (14) | 0.0470 (13) | 0.0161 (15) | 0.0076 (14) | −0.0008 (11) |
C7B | 0.090 (2) | 0.0540 (14) | 0.0571 (15) | −0.0117 (14) | 0.0107 (14) | 0.0002 (12) |
O8 | 0.0790 (14) | 0.0651 (11) | 0.0748 (13) | 0.0193 (10) | −0.0075 (10) | −0.0186 (10) |
O6 | 0.0679 (11) | 0.0546 (9) | 0.0671 (11) | 0.0136 (8) | 0.0076 (9) | −0.0152 (8) |
O7 | 0.1071 (16) | 0.0516 (10) | 0.0669 (12) | 0.0068 (10) | 0.0182 (11) | 0.0051 (9) |
O1 | 0.0874 (14) | 0.0471 (9) | 0.0987 (15) | −0.0010 (9) | 0.0198 (12) | −0.0165 (10) |
O2 | 0.0788 (14) | 0.0699 (13) | 0.0952 (15) | −0.0102 (10) | 0.0098 (12) | −0.0327 (11) |
N2 | 0.0592 (11) | 0.0307 (8) | 0.0496 (10) | 0.0048 (7) | 0.0135 (8) | −0.0011 (7) |
N1 | 0.0559 (11) | 0.0428 (9) | 0.0457 (10) | 0.0064 (8) | 0.0112 (8) | −0.0007 (7) |
C28 | 0.0678 (19) | 0.116 (3) | 0.073 (2) | 0.0119 (19) | 0.0171 (16) | 0.0074 (19) |
C29 | 0.0673 (18) | 0.105 (2) | 0.0624 (17) | 0.0098 (16) | 0.0094 (14) | −0.0033 (16) |
O3 | 0.0812 (15) | 0.0996 (18) | 0.0864 (16) | 0.0112 (12) | 0.0042 (12) | −0.0304 (13) |
C30 | 0.0594 (15) | 0.0765 (17) | 0.0596 (15) | 0.0072 (13) | 0.0023 (12) | 0.0011 (13) |
C31 | 0.0628 (15) | 0.0504 (13) | 0.0681 (16) | 0.0034 (11) | −0.0022 (12) | 0.0182 (12) |
C22 | 0.0740 (18) | 0.0412 (12) | 0.0770 (18) | 0.0048 (11) | −0.0132 (14) | 0.0059 (12) |
C21 | 0.097 (2) | 0.0560 (15) | 0.0661 (17) | 0.0203 (14) | −0.0103 (15) | −0.0123 (13) |
C20 | 0.0883 (19) | 0.0448 (12) | 0.0546 (14) | 0.0144 (12) | 0.0102 (13) | −0.0055 (10) |
C19 | 0.0596 (14) | 0.0394 (11) | 0.0632 (14) | 0.0059 (10) | 0.0074 (11) | −0.0017 (10) |
C16 | 0.0615 (14) | 0.0461 (11) | 0.0505 (12) | 0.0067 (10) | 0.0204 (11) | 0.0029 (9) |
C15 | 0.0672 (15) | 0.0551 (13) | 0.0459 (12) | 0.0083 (11) | 0.0148 (11) | −0.0031 (10) |
C14 | 0.0527 (13) | 0.0396 (10) | 0.0553 (13) | 0.0016 (9) | 0.0096 (10) | 0.0004 (9) |
C9 | 0.0531 (13) | 0.0422 (11) | 0.0609 (14) | 0.0000 (9) | 0.0101 (11) | −0.0008 (10) |
C8 | 0.097 (2) | 0.0640 (17) | 0.082 (2) | 0.0193 (16) | 0.0189 (17) | −0.0219 (15) |
C27 | 0.0605 (18) | 0.101 (2) | 0.094 (2) | 0.0098 (17) | 0.0168 (17) | 0.034 (2) |
C26 | 0.0608 (16) | 0.0604 (15) | 0.089 (2) | −0.0046 (13) | −0.0058 (15) | 0.0307 (15) |
C25 | 0.076 (2) | 0.0609 (18) | 0.135 (3) | −0.0130 (16) | −0.019 (2) | 0.022 (2) |
C24 | 0.097 (3) | 0.0568 (18) | 0.145 (4) | −0.0129 (18) | −0.040 (3) | −0.005 (2) |
C23 | 0.109 (3) | 0.0494 (15) | 0.102 (3) | 0.0025 (15) | −0.028 (2) | −0.0092 (15) |
C13 | 0.0721 (17) | 0.0559 (14) | 0.0590 (15) | 0.0029 (12) | 0.0021 (13) | −0.0042 (11) |
C12 | 0.0753 (19) | 0.0721 (18) | 0.0658 (17) | −0.0014 (15) | −0.0080 (14) | 0.0048 (14) |
C11 | 0.0640 (17) | 0.0646 (16) | 0.084 (2) | 0.0035 (13) | −0.0059 (15) | 0.0152 (15) |
C10 | 0.0576 (15) | 0.0495 (13) | 0.0836 (19) | 0.0080 (11) | 0.0088 (13) | 0.0045 (12) |
C18 | 0.0602 (14) | 0.0478 (12) | 0.0545 (13) | 0.0068 (10) | 0.0198 (11) | 0.0034 (10) |
C17 | 0.0654 (15) | 0.0445 (11) | 0.0467 (12) | 0.0125 (10) | 0.0172 (10) | 0.0006 (9) |
C5 | 0.121 (3) | 0.0498 (14) | 0.0484 (14) | −0.0142 (15) | −0.0026 (16) | −0.0024 (11) |
C3 | 0.0775 (18) | 0.0616 (14) | 0.0407 (12) | −0.0046 (13) | 0.0041 (11) | −0.0039 (10) |
C2 | 0.0778 (17) | 0.0403 (10) | 0.0429 (11) | −0.0072 (10) | 0.0151 (11) | 0.0002 (9) |
C1 | 0.086 (2) | 0.0474 (13) | 0.0575 (14) | −0.0150 (13) | 0.0215 (14) | −0.0073 (11) |
C6 | 0.092 (2) | 0.0626 (17) | 0.0648 (17) | −0.0179 (15) | 0.0026 (15) | −0.0029 (13) |
C4A—O4 | 1.259 (5) | C28—C29 | 1.404 (4) |
C4A—C5 | 1.349 (5) | C29—C30 | 1.359 (4) |
C4A—C3 | 1.414 (4) | O3—C3 | 1.332 (3) |
C7A—O5 | 1.080 (8) | C30—C31 | 1.409 (4) |
C7A—C2 | 1.381 (4) | C31—C22 | 1.423 (4) |
C7A—C6 | 1.384 (4) | C31—C26 | 1.430 (4) |
C4B—C5 | 1.349 (5) | C22—C23 | 1.363 (4) |
C4B—C3 | 1.414 (4) | C21—C20 | 1.512 (4) |
C7B—C2 | 1.381 (4) | C20—C19 | 1.525 (4) |
C7B—C6 | 1.384 (4) | C16—C15 | 1.499 (4) |
O8—C22 | 1.365 (3) | C14—C13 | 1.384 (4) |
O8—C21 | 1.431 (3) | C14—C9 | 1.410 (3) |
O6—C9 | 1.370 (3) | C9—C10 | 1.387 (4) |
O6—C8 | 1.430 (3) | C27—C26 | 1.417 (5) |
O7—C20 | 1.401 (3) | C26—C25 | 1.416 (5) |
O1—C1 | 1.245 (3) | C25—C24 | 1.355 (6) |
O2—C1 | 1.263 (4) | C24—C23 | 1.413 (6) |
N2—C19 | 1.489 (3) | C13—C12 | 1.390 (4) |
N2—C16 | 1.501 (3) | C12—C11 | 1.365 (4) |
N2—C17 | 1.503 (3) | C11—C10 | 1.392 (4) |
N1—C14 | 1.433 (3) | C18—C17 | 1.502 (3) |
N1—C15 | 1.460 (3) | C5—C6 | 1.367 (5) |
N1—C18 | 1.470 (3) | C3—C2 | 1.384 (4) |
C28—C27 | 1.355 (5) | C2—C1 | 1.513 (3) |
O4—C4A—C5 | 122.9 (4) | C9—C14—N1 | 118.7 (2) |
O4—C4A—C3 | 116.2 (4) | O6—C9—C10 | 124.4 (2) |
C5—C4A—C3 | 120.8 (3) | O6—C9—C14 | 115.8 (2) |
O5—C7A—C2 | 117.6 (6) | C10—C9—C14 | 119.8 (2) |
O5—C7A—C6 | 120.2 (6) | C28—C27—C26 | 121.7 (3) |
C2—C7A—C6 | 121.9 (3) | C25—C26—C27 | 123.5 (3) |
C5—C4B—C3 | 120.8 (3) | C25—C26—C31 | 118.3 (3) |
C2—C7B—C6 | 121.9 (3) | C27—C26—C31 | 118.1 (3) |
C22—O8—C21 | 119.0 (2) | C24—C25—C26 | 120.7 (4) |
C9—O6—C8 | 117.2 (2) | C25—C24—C23 | 121.7 (3) |
C19—N2—C16 | 109.28 (18) | C22—C23—C24 | 119.1 (4) |
C19—N2—C17 | 112.59 (18) | C14—C13—C12 | 121.9 (3) |
C16—N2—C17 | 110.74 (16) | C11—C12—C13 | 119.4 (3) |
C14—N1—C15 | 115.97 (19) | C12—C11—C10 | 120.5 (3) |
C14—N1—C18 | 114.97 (18) | C9—C10—C11 | 120.3 (3) |
C15—N1—C18 | 108.53 (17) | N1—C18—C17 | 110.06 (19) |
C27—C28—C29 | 120.0 (3) | C18—C17—N2 | 111.97 (19) |
C30—C29—C28 | 120.2 (3) | C4B—C5—C6 | 120.7 (3) |
C29—C30—C31 | 121.8 (3) | C4A—C5—C6 | 120.7 (3) |
C30—C31—C22 | 123.0 (3) | O3—C3—C2 | 122.8 (2) |
C30—C31—C26 | 118.2 (3) | O3—C3—C4B | 118.1 (3) |
C22—C31—C26 | 118.8 (3) | C2—C3—C4B | 119.1 (3) |
C23—C22—O8 | 125.0 (3) | O3—C3—C4A | 118.1 (3) |
C23—C22—C31 | 121.1 (3) | C2—C3—C4A | 119.1 (3) |
O8—C22—C31 | 113.9 (2) | C7B—C2—C3 | 118.4 (2) |
O8—C21—C20 | 106.5 (2) | C7A—C2—C3 | 118.4 (2) |
O7—C20—C21 | 112.7 (2) | C7B—C2—C1 | 121.5 (3) |
O7—C20—C19 | 111.5 (2) | C7A—C2—C1 | 121.5 (3) |
C21—C20—C19 | 110.0 (2) | C3—C2—C1 | 120.1 (3) |
N2—C19—C20 | 114.4 (2) | O1—C1—O2 | 123.4 (2) |
C15—C16—N2 | 112.17 (19) | O1—C1—C2 | 118.9 (3) |
N1—C15—C16 | 109.93 (19) | O2—C1—C2 | 117.7 (3) |
C13—C14—C9 | 118.1 (2) | C5—C6—C7A | 119.1 (3) |
C13—C14—N1 | 123.1 (2) | C5—C6—C7B | 119.1 (3) |
C62H68.91N4O13.03 | F(000) = 1146 |
Mr = 1078.60 | Dx = 1.341 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.246 (10) Å | Cell parameters from 7319 reflections |
b = 17.607 (16) Å | θ = 2.7–28.8° |
c = 13.523 (13) Å | µ = 0.09 mm−1 |
β = 94.19 (4)° | T = 100 K |
V = 2670 (4) Å3 | Block, colourless |
Z = 2 | 0.2 × 0.15 × 0.15 mm |
Bruker APEX-II CCD diffractometer | 8744 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.112 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1017 before and 0.0677 after correction. The Ratio of minimum to maximum transmission is 0.8961. The λ/2 correction factor is Not present. | θmax = 30.4°, θmin = 2.3° |
Tmin = 0.669, Tmax = 0.746 | h = −16→16 |
63374 measured reflections | k = −25→25 |
16100 independent reflections | l = −18→19 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.097 | w = 1/[σ2(Fo2) + (0.0494P)2 + 3.0015P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.198 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.54 e Å−3 |
16100 reflections | Δρmin = −0.29 e Å−3 |
730 parameters | Absolute structure: Flack x determined using 2529 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
1 restraint | Absolute structure parameter: −0.6 (9) |
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) | |
C34A | 0.6524 (8) | 0.4234 (5) | 0.8932 (6) | 0.044 (2) | 0.51 |
O11 | 0.7181 (13) | 0.3706 (9) | 0.8990 (13) | 0.103 (6) | 0.51 |
H11A | 0.680944 | 0.331258 | 0.880012 | 0.155* | 0.51 |
C5A | 0.4009 (6) | 0.4612 (5) | 0.5557 (5) | 0.0356 (17) | 0.52 |
O4 | 0.3583 (7) | 0.4014 (4) | 0.5005 (6) | 0.0317 (18) | 0.52 |
H4 | 0.397914 | 0.362338 | 0.516644 | 0.048* | 0.52 |
C34B | 0.6524 (8) | 0.4234 (5) | 0.8932 (6) | 0.044 (2) | 0.49 |
H34B | 0.715062 | 0.387941 | 0.886893 | 0.053* | 0.4 |
C5B | 0.4009 (6) | 0.4612 (5) | 0.5557 (5) | 0.0356 (17) | 0.48 |
H5B | 0.377398 | 0.415582 | 0.522258 | 0.043* | 0.48 |
O5 | 0.2110 (4) | 1.0588 (2) | 0.7967 (3) | 0.0281 (10) | |
O2 | 0.6029 (5) | 0.6693 (3) | 0.7597 (4) | 0.0460 (14) | |
O14 | 0.2173 (4) | 0.2536 (3) | 0.5659 (4) | 0.0397 (13) | |
O13 | 0.4653 (4) | 0.2728 (3) | 0.5644 (4) | 0.0385 (12) | |
H13A | 0.440499 | 0.294479 | 0.614200 | 0.058* | |
O8 | 0.6012 (4) | 0.2874 (3) | 0.7883 (4) | 0.0423 (13) | |
O1 | 0.4182 (5) | 0.7155 (3) | 0.7228 (5) | 0.0486 (14) | |
H1 | 0.447554 | 0.758732 | 0.714497 | 0.073* | |
O12 | 0.8160 (4) | −0.0581 (3) | 0.7036 (4) | 0.0340 (11) | |
O10 | 0.3385 (5) | 0.4468 (4) | 0.8199 (5) | 0.0527 (15) | |
H10A | 0.331841 | 0.401156 | 0.802279 | 0.079* | |
N3 | 0.5226 (5) | 0.1539 (3) | 0.7047 (4) | 0.0265 (12) | |
H3 | 0.550250 | 0.206903 | 0.719739 | 0.032* | |
N4 | 0.7026 (5) | 0.0536 (3) | 0.7948 (4) | 0.0276 (12) | |
N1 | 0.3257 (5) | 0.9452 (3) | 0.7087 (4) | 0.0279 (12) | |
O7 | 0.8055 (5) | 0.7361 (3) | 0.9418 (4) | 0.0429 (13) | |
O6 | 0.5605 (5) | 0.7309 (3) | 0.9497 (4) | 0.0472 (14) | |
H6 | 0.596372 | 0.701161 | 0.913418 | 0.071* | |
O3 | 0.6623 (5) | 0.5405 (4) | 0.6899 (5) | 0.0506 (15) | |
H3A | 0.669627 | 0.579964 | 0.724738 | 0.076* | |
N2 | 0.5059 (5) | 0.8460 (3) | 0.8014 (4) | 0.0295 (13) | |
H2 | 0.475855 | 0.793551 | 0.785815 | 0.035* | |
C18 | 0.4019 (6) | 0.9008 (4) | 0.6477 (5) | 0.0330 (16) | |
H18A | 0.414533 | 0.928738 | 0.585774 | 0.040* | |
H18B | 0.362861 | 0.851829 | 0.629599 | 0.040* | |
C14 | 0.2220 (6) | 0.9787 (4) | 0.6577 (5) | 0.0286 (14) | |
C50 | 0.4035 (6) | 0.1583 (3) | 0.6500 (5) | 0.0280 (14) | |
H50A | 0.347502 | 0.184531 | 0.691730 | 0.034* | |
H50B | 0.373006 | 0.106218 | 0.636951 | 0.034* | |
C47 | 0.6139 (6) | 0.1159 (4) | 0.6459 (6) | 0.0314 (16) | |
H47A | 0.631323 | 0.148995 | 0.589505 | 0.038* | |
H47B | 0.580740 | 0.067632 | 0.618402 | 0.038* | |
C11 | 0.0240 (6) | 1.0492 (4) | 0.5617 (5) | 0.0316 (16) | |
H11 | −0.043804 | 1.072738 | 0.528851 | 0.038* | |
C40 | 0.8635 (5) | −0.0396 (4) | 0.7966 (5) | 0.0283 (14) | |
C3 | 0.5490 (6) | 0.5354 (4) | 0.6494 (5) | 0.0308 (15) | |
C53 | 0.0943 (6) | 0.2594 (4) | 0.5500 (6) | 0.0347 (17) | |
C62 | 0.0406 (6) | 0.3040 (4) | 0.6236 (5) | 0.0309 (15) | |
C39 | 0.8710 (6) | −0.1206 (4) | 0.6543 (6) | 0.0370 (18) | |
H39A | 0.827167 | −0.130176 | 0.590174 | 0.055* | |
H39B | 0.869121 | −0.166271 | 0.695608 | 0.055* | |
H39C | 0.953903 | −0.107737 | 0.643731 | 0.055* | |
C9 | 0.1635 (6) | 1.0374 (3) | 0.7054 (5) | 0.0279 (14) | |
C29 | 0.9475 (6) | 0.5967 (5) | 0.7358 (6) | 0.0403 (18) | |
H29 | 0.896463 | 0.568689 | 0.690062 | 0.048* | |
C20 | 0.6227 (7) | 0.8004 (4) | 0.9583 (6) | 0.0425 (19) | |
H20 | 0.579644 | 0.834311 | 1.003051 | 0.051* | |
C10 | 0.0634 (6) | 1.0722 (4) | 0.6557 (5) | 0.0300 (15) | |
H10 | 0.022873 | 1.111767 | 0.687248 | 0.036* | |
C48 | 0.5099 (6) | 0.1138 (3) | 0.8016 (5) | 0.0261 (14) | |
H48A | 0.460293 | 0.145179 | 0.843218 | 0.031* | |
H48B | 0.468140 | 0.064933 | 0.788543 | 0.031* | |
C33 | 0.5401 (7) | 0.4064 (4) | 0.8516 (5) | 0.0327 (16) | |
C44 | 0.8488 (6) | 0.0409 (4) | 0.9419 (6) | 0.0382 (17) | |
H44 | 0.811762 | 0.081233 | 0.974760 | 0.046* | |
C1 | 0.4992 (8) | 0.6649 (4) | 0.7169 (6) | 0.043 (2) | |
C46 | 0.7283 (6) | 0.0997 (4) | 0.7073 (6) | 0.0349 (16) | |
H46A | 0.783942 | 0.071858 | 0.666864 | 0.042* | |
H46B | 0.766666 | 0.148043 | 0.729259 | 0.042* | |
C26 | 1.0990 (8) | 0.6787 (4) | 0.8715 (6) | 0.0425 (19) | |
C32 | 0.5179 (6) | 0.3333 (4) | 0.7933 (6) | 0.0332 (16) | |
C45 | 0.8053 (6) | 0.0198 (4) | 0.8449 (5) | 0.0283 (14) | |
C6 | 0.3189 (7) | 0.5202 (5) | 0.5619 (6) | 0.0394 (18) | |
H6A | 0.240304 | 0.514763 | 0.531874 | 0.047* | 0.52 |
H6B | 0.240304 | 0.514763 | 0.531874 | 0.047* | 0.48 |
C17 | 0.5217 (6) | 0.8862 (4) | 0.7050 (5) | 0.0319 (16) | |
H17A | 0.572211 | 0.854842 | 0.664000 | 0.038* | |
H17B | 0.562896 | 0.935141 | 0.718568 | 0.038* | |
C15 | 0.3012 (6) | 0.9007 (4) | 0.7977 (5) | 0.0288 (14) | |
H15A | 0.263319 | 0.851844 | 0.777277 | 0.035* | |
H15B | 0.245247 | 0.929055 | 0.837245 | 0.035* | |
C12 | 0.0828 (6) | 0.9917 (4) | 0.5145 (5) | 0.0337 (16) | |
H12 | 0.056175 | 0.976489 | 0.449233 | 0.040* | |
C61 | 0.1085 (6) | 0.3434 (5) | 0.6984 (5) | 0.0366 (17) | |
H61 | 0.192791 | 0.337881 | 0.704611 | 0.044* | |
C16 | 0.4158 (6) | 0.8858 (3) | 0.8599 (5) | 0.0280 (14) | |
H16A | 0.449446 | 0.934663 | 0.885051 | 0.034* | |
H16B | 0.398656 | 0.854207 | 0.917684 | 0.034* | |
C52 | 0.2813 (7) | 0.2060 (4) | 0.5020 (6) | 0.0399 (18) | |
H52A | 0.281447 | 0.228468 | 0.434888 | 0.048* | |
H52B | 0.244642 | 0.154869 | 0.496334 | 0.048* | |
C41 | 0.9611 (6) | −0.0759 (4) | 0.8450 (6) | 0.0355 (17) | |
H41 | 1.000034 | −0.115625 | 0.812407 | 0.043* | |
C30 | 0.8994 (6) | 0.6436 (4) | 0.8051 (5) | 0.0320 (16) | |
H30 | 0.815190 | 0.648033 | 0.805270 | 0.038* | |
C23 | 0.9981 (9) | 0.7626 (4) | 1.0230 (7) | 0.054 (2) | |
H23 | 0.964284 | 0.789295 | 1.075177 | 0.065* | |
O9 | 0.4144 (4) | 0.3224 (3) | 0.7512 (4) | 0.0387 (13) | |
C28 | 1.0737 (7) | 0.5908 (6) | 0.7334 (6) | 0.050 (2) | |
H28 | 1.107604 | 0.558834 | 0.686282 | 0.060* | |
C13 | 0.1800 (6) | 0.9570 (3) | 0.5632 (5) | 0.0281 (14) | |
H13 | 0.219071 | 0.917092 | 0.531132 | 0.034* | |
C58 | −0.1377 (7) | 0.3556 (5) | 0.6911 (7) | 0.047 (2) | |
H58 | −0.222015 | 0.358092 | 0.692298 | 0.056* | |
C56 | −0.1525 (7) | 0.2731 (5) | 0.5413 (7) | 0.049 (2) | |
H56 | −0.237099 | 0.273494 | 0.540235 | 0.058* | |
C57 | −0.0868 (6) | 0.3092 (4) | 0.6168 (6) | 0.0371 (17) | |
C42 | 1.0029 (6) | −0.0544 (4) | 0.9418 (6) | 0.0395 (18) | |
H42 | 1.069835 | −0.079293 | 0.974239 | 0.047* | |
C4 | 0.5158 (7) | 0.4686 (4) | 0.5979 (5) | 0.0347 (16) | |
H4A | 0.572000 | 0.428793 | 0.592003 | 0.042* | 0.52 |
H4B | 0.572000 | 0.428793 | 0.592003 | 0.042* | 0.48 |
C37 | 0.4748 (8) | 0.5291 (5) | 0.9070 (6) | 0.045 (2) | |
H37 | 0.414480 | 0.566664 | 0.909527 | 0.054* | |
C31 | 0.9723 (7) | 0.6848 (4) | 0.8750 (6) | 0.0366 (17) | |
C51 | 0.4080 (6) | 0.2012 (4) | 0.5506 (6) | 0.0331 (16) | |
H51 | 0.456271 | 0.169961 | 0.506525 | 0.040* | |
C7 | 0.3509 (7) | 0.5854 (4) | 0.6105 (5) | 0.0387 (18) | |
H7 | 0.294600 | 0.625422 | 0.613186 | 0.046* | |
C38 | 0.4489 (7) | 0.4594 (5) | 0.8591 (6) | 0.0417 (19) | |
C54 | 0.0298 (7) | 0.2275 (4) | 0.4704 (7) | 0.047 (2) | |
H54 | 0.067366 | 0.200993 | 0.419958 | 0.056* | |
C27 | 1.1470 (7) | 0.6327 (5) | 0.8016 (6) | 0.046 (2) | |
H27 | 1.231132 | 0.629500 | 0.799734 | 0.055* | |
C22 | 0.9247 (8) | 0.7298 (4) | 0.9506 (6) | 0.0426 (19) | |
C2 | 0.4665 (7) | 0.5947 (4) | 0.6573 (5) | 0.0321 (16) | |
C43 | 0.9456 (6) | 0.0031 (4) | 0.9893 (6) | 0.0376 (17) | |
H43 | 0.972686 | 0.016998 | 1.055068 | 0.045* | |
C59 | −0.0691 (7) | 0.3958 (5) | 0.7593 (6) | 0.0404 (18) | |
H59 | −0.104986 | 0.428165 | 0.804857 | 0.048* | |
C49 | 0.6267 (6) | 0.0989 (4) | 0.8569 (5) | 0.0313 (15) | |
H49A | 0.666526 | 0.147625 | 0.874808 | 0.038* | |
H49B | 0.614097 | 0.071005 | 0.918806 | 0.038* | |
C19 | 0.6246 (7) | 0.8393 (4) | 0.8582 (6) | 0.0376 (17) | |
H19A | 0.658128 | 0.890949 | 0.868602 | 0.045* | |
H19B | 0.678958 | 0.810794 | 0.817372 | 0.045* | |
C8 | 0.1521 (7) | 1.1184 (4) | 0.8458 (6) | 0.0372 (17) | |
H8A | 0.156325 | 1.165463 | 0.807457 | 0.056* | |
H8B | 0.191316 | 1.126052 | 0.912195 | 0.056* | |
H8C | 0.068468 | 1.104649 | 0.851371 | 0.056* | |
C25 | 1.1732 (8) | 0.7190 (5) | 0.9492 (7) | 0.055 (2) | |
H25 | 1.257587 | 0.718090 | 0.948740 | 0.066* | |
C21 | 0.7471 (8) | 0.7884 (4) | 1.0046 (6) | 0.050 (2) | |
H21A | 0.790870 | 0.837216 | 1.009291 | 0.060* | |
H21B | 0.744489 | 0.767075 | 1.072120 | 0.060* | |
C24 | 1.1197 (9) | 0.7578 (5) | 1.0222 (8) | 0.059 (3) | |
H24 | 1.168253 | 0.781998 | 1.073332 | 0.071* | |
C60 | 0.0542 (7) | 0.3892 (5) | 0.7617 (6) | 0.0396 (18) | |
H60 | 0.101919 | 0.417679 | 0.809269 | 0.048* | |
C35 | 0.6771 (8) | 0.4913 (4) | 0.9445 (6) | 0.0423 (19) | |
H35 | 0.754403 | 0.501629 | 0.974610 | 0.051* | 0.6 |
H35A | 0.754403 | 0.501629 | 0.974610 | 0.051* | 0.4 |
C36 | 0.5855 (8) | 0.5425 (4) | 0.9496 (5) | 0.046 (2) | |
H36 | 0.600321 | 0.588927 | 0.984179 | 0.055* | |
C55 | −0.0979 (9) | 0.2364 (5) | 0.4673 (8) | 0.062 (3) | |
H55 | −0.145597 | 0.216324 | 0.412551 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C34A | 0.062 (5) | 0.029 (4) | 0.042 (5) | −0.017 (3) | 0.007 (4) | −0.003 (3) |
O11 | 0.085 (10) | 0.110 (12) | 0.113 (12) | 0.071 (9) | −0.008 (9) | −0.051 (10) |
C5A | 0.045 (4) | 0.042 (4) | 0.020 (4) | −0.010 (3) | 0.003 (3) | 0.000 (3) |
O4 | 0.044 (5) | 0.027 (4) | 0.024 (4) | −0.002 (4) | −0.006 (4) | −0.001 (3) |
C34B | 0.062 (5) | 0.029 (4) | 0.042 (5) | −0.017 (3) | 0.007 (4) | −0.003 (3) |
C5B | 0.045 (4) | 0.042 (4) | 0.020 (4) | −0.010 (3) | 0.003 (3) | 0.000 (3) |
O5 | 0.044 (3) | 0.016 (2) | 0.025 (2) | 0.0086 (18) | 0.009 (2) | −0.0045 (18) |
O2 | 0.057 (3) | 0.032 (3) | 0.050 (4) | −0.010 (2) | 0.010 (3) | −0.013 (3) |
O14 | 0.046 (3) | 0.036 (3) | 0.038 (3) | 0.009 (2) | 0.007 (2) | −0.012 (2) |
O13 | 0.049 (3) | 0.017 (2) | 0.051 (3) | 0.002 (2) | 0.014 (2) | −0.001 (2) |
O8 | 0.047 (3) | 0.025 (3) | 0.057 (4) | −0.003 (2) | 0.017 (3) | −0.012 (2) |
O1 | 0.076 (4) | 0.009 (2) | 0.060 (4) | 0.004 (2) | 0.006 (3) | −0.005 (2) |
O12 | 0.033 (2) | 0.025 (2) | 0.044 (3) | 0.0071 (19) | 0.006 (2) | −0.008 (2) |
O10 | 0.061 (4) | 0.047 (3) | 0.050 (4) | 0.016 (3) | 0.007 (3) | −0.022 (3) |
N3 | 0.034 (3) | 0.014 (2) | 0.033 (3) | 0.001 (2) | 0.010 (2) | −0.003 (2) |
N4 | 0.036 (3) | 0.018 (3) | 0.029 (3) | 0.001 (2) | 0.007 (2) | −0.001 (2) |
N1 | 0.042 (3) | 0.018 (3) | 0.025 (3) | 0.004 (2) | 0.012 (2) | 0.001 (2) |
O7 | 0.062 (3) | 0.024 (2) | 0.043 (3) | 0.010 (2) | −0.004 (3) | −0.004 (2) |
O6 | 0.082 (4) | 0.019 (2) | 0.042 (3) | 0.009 (3) | 0.018 (3) | 0.007 (2) |
O3 | 0.048 (3) | 0.049 (3) | 0.056 (4) | −0.006 (3) | 0.010 (3) | −0.022 (3) |
N2 | 0.045 (3) | 0.014 (2) | 0.031 (3) | 0.004 (2) | 0.015 (3) | 0.003 (2) |
C18 | 0.050 (4) | 0.023 (3) | 0.028 (4) | 0.007 (3) | 0.015 (3) | 0.005 (3) |
C14 | 0.038 (3) | 0.015 (3) | 0.035 (4) | −0.003 (3) | 0.013 (3) | 0.004 (3) |
C50 | 0.041 (4) | 0.012 (3) | 0.032 (4) | −0.002 (3) | 0.008 (3) | 0.004 (3) |
C47 | 0.037 (4) | 0.022 (3) | 0.036 (4) | 0.003 (3) | 0.012 (3) | −0.005 (3) |
C11 | 0.038 (4) | 0.021 (3) | 0.035 (4) | −0.007 (3) | −0.001 (3) | 0.013 (3) |
C40 | 0.032 (3) | 0.021 (3) | 0.032 (4) | −0.004 (3) | 0.002 (3) | −0.001 (3) |
C3 | 0.045 (4) | 0.026 (3) | 0.021 (3) | −0.009 (3) | 0.004 (3) | −0.013 (3) |
C53 | 0.043 (4) | 0.015 (3) | 0.046 (5) | −0.004 (3) | 0.004 (3) | 0.007 (3) |
C62 | 0.043 (4) | 0.019 (3) | 0.032 (4) | 0.005 (3) | 0.006 (3) | 0.014 (3) |
C39 | 0.043 (4) | 0.029 (4) | 0.041 (4) | 0.006 (3) | 0.016 (3) | −0.020 (3) |
C9 | 0.041 (4) | 0.013 (3) | 0.031 (4) | −0.003 (2) | 0.011 (3) | −0.001 (3) |
C29 | 0.039 (4) | 0.047 (4) | 0.035 (4) | 0.007 (3) | 0.002 (3) | −0.006 (4) |
C20 | 0.072 (5) | 0.025 (4) | 0.032 (4) | 0.006 (4) | 0.014 (4) | −0.005 (3) |
C10 | 0.038 (4) | 0.013 (3) | 0.040 (4) | 0.000 (3) | 0.007 (3) | 0.002 (3) |
C48 | 0.036 (3) | 0.014 (3) | 0.030 (4) | 0.003 (2) | 0.013 (3) | −0.004 (3) |
C33 | 0.053 (4) | 0.020 (3) | 0.026 (4) | −0.004 (3) | 0.014 (3) | −0.004 (3) |
C44 | 0.046 (4) | 0.033 (4) | 0.036 (4) | 0.000 (3) | 0.008 (3) | −0.004 (3) |
C1 | 0.079 (6) | 0.020 (4) | 0.032 (4) | −0.011 (4) | 0.020 (4) | −0.001 (3) |
C46 | 0.038 (4) | 0.027 (3) | 0.041 (4) | 0.003 (3) | 0.014 (3) | −0.002 (3) |
C26 | 0.070 (5) | 0.020 (3) | 0.037 (4) | −0.003 (3) | 0.002 (4) | 0.018 (3) |
C32 | 0.040 (4) | 0.027 (4) | 0.034 (4) | −0.013 (3) | 0.013 (3) | −0.007 (3) |
C45 | 0.036 (3) | 0.018 (3) | 0.033 (4) | −0.003 (3) | 0.011 (3) | −0.003 (3) |
C6 | 0.050 (4) | 0.038 (4) | 0.029 (4) | −0.002 (3) | −0.004 (3) | 0.002 (3) |
C17 | 0.045 (4) | 0.025 (3) | 0.028 (4) | 0.005 (3) | 0.016 (3) | 0.009 (3) |
C15 | 0.043 (4) | 0.016 (3) | 0.029 (3) | 0.002 (3) | 0.012 (3) | 0.003 (3) |
C12 | 0.045 (4) | 0.027 (3) | 0.028 (4) | −0.007 (3) | −0.001 (3) | 0.006 (3) |
C61 | 0.037 (4) | 0.045 (4) | 0.028 (4) | 0.007 (3) | 0.005 (3) | 0.010 (3) |
C16 | 0.052 (4) | 0.009 (3) | 0.025 (3) | 0.002 (2) | 0.015 (3) | 0.000 (2) |
C52 | 0.058 (5) | 0.031 (4) | 0.029 (4) | 0.009 (3) | −0.001 (3) | 0.002 (3) |
C41 | 0.036 (4) | 0.022 (3) | 0.050 (5) | −0.002 (3) | 0.013 (3) | 0.000 (3) |
C30 | 0.034 (4) | 0.029 (4) | 0.032 (4) | 0.006 (3) | −0.004 (3) | 0.007 (3) |
C23 | 0.097 (7) | 0.015 (3) | 0.047 (5) | 0.008 (4) | −0.013 (5) | −0.008 (3) |
O9 | 0.041 (3) | 0.028 (3) | 0.048 (3) | −0.003 (2) | 0.015 (2) | −0.011 (2) |
C28 | 0.051 (5) | 0.062 (5) | 0.038 (5) | 0.009 (4) | 0.013 (4) | 0.009 (4) |
C13 | 0.041 (4) | 0.012 (3) | 0.032 (4) | −0.010 (3) | 0.005 (3) | −0.006 (3) |
C58 | 0.035 (4) | 0.038 (4) | 0.069 (6) | 0.001 (3) | 0.018 (4) | 0.021 (4) |
C56 | 0.044 (4) | 0.027 (4) | 0.073 (6) | −0.007 (3) | −0.006 (4) | 0.016 (4) |
C57 | 0.038 (4) | 0.025 (3) | 0.048 (5) | 0.000 (3) | −0.003 (3) | 0.015 (3) |
C42 | 0.031 (4) | 0.034 (4) | 0.052 (5) | −0.001 (3) | −0.002 (3) | −0.001 (4) |
C4 | 0.054 (4) | 0.018 (3) | 0.032 (4) | −0.001 (3) | 0.003 (3) | −0.005 (3) |
C37 | 0.079 (6) | 0.029 (4) | 0.027 (4) | 0.016 (4) | 0.014 (4) | 0.001 (3) |
C31 | 0.044 (4) | 0.023 (3) | 0.042 (4) | 0.009 (3) | −0.001 (3) | 0.018 (3) |
C51 | 0.053 (4) | 0.011 (3) | 0.036 (4) | 0.005 (3) | 0.015 (3) | −0.003 (3) |
C7 | 0.068 (5) | 0.032 (4) | 0.016 (3) | 0.005 (3) | −0.002 (3) | 0.006 (3) |
C38 | 0.053 (5) | 0.040 (4) | 0.034 (4) | −0.007 (4) | 0.009 (3) | 0.003 (4) |
C54 | 0.063 (5) | 0.022 (3) | 0.054 (5) | −0.002 (3) | −0.004 (4) | 0.003 (4) |
C27 | 0.040 (4) | 0.053 (5) | 0.043 (5) | −0.003 (4) | 0.000 (4) | 0.017 (4) |
C22 | 0.075 (6) | 0.013 (3) | 0.039 (4) | 0.010 (3) | −0.001 (4) | 0.009 (3) |
C2 | 0.064 (5) | 0.012 (3) | 0.023 (3) | −0.006 (3) | 0.020 (3) | 0.003 (3) |
C43 | 0.044 (4) | 0.031 (4) | 0.037 (4) | −0.009 (3) | −0.007 (3) | −0.001 (3) |
C59 | 0.046 (4) | 0.039 (4) | 0.037 (4) | 0.016 (3) | 0.016 (3) | 0.006 (4) |
C49 | 0.038 (4) | 0.028 (3) | 0.030 (4) | 0.001 (3) | 0.014 (3) | −0.010 (3) |
C19 | 0.051 (4) | 0.026 (4) | 0.036 (4) | 0.010 (3) | 0.004 (3) | −0.006 (3) |
C8 | 0.049 (4) | 0.023 (3) | 0.041 (4) | 0.008 (3) | 0.006 (3) | 0.001 (3) |
C25 | 0.050 (5) | 0.039 (5) | 0.072 (6) | −0.013 (4) | −0.017 (4) | 0.020 (5) |
C21 | 0.090 (6) | 0.019 (3) | 0.040 (5) | 0.025 (4) | −0.007 (4) | −0.005 (3) |
C24 | 0.078 (6) | 0.020 (4) | 0.078 (7) | 0.000 (4) | −0.006 (5) | −0.014 (4) |
C60 | 0.051 (4) | 0.041 (4) | 0.027 (4) | 0.009 (3) | 0.007 (3) | 0.005 (3) |
C35 | 0.071 (5) | 0.022 (3) | 0.034 (4) | −0.004 (3) | 0.008 (4) | −0.002 (3) |
C36 | 0.096 (6) | 0.022 (4) | 0.018 (4) | −0.019 (4) | 0.002 (4) | −0.001 (3) |
C55 | 0.078 (6) | 0.033 (4) | 0.070 (6) | −0.029 (4) | −0.040 (5) | 0.021 (5) |
C34A—O11 | 1.186 (14) | C48—H48A | 0.9900 |
C34A—C33 | 1.378 (11) | C48—H48B | 0.9900 |
C34A—C35 | 1.399 (11) | C33—C38 | 1.395 (11) |
O11—H11A | 0.8400 | C33—C32 | 1.520 (10) |
C5A—O4 | 1.357 (10) | C44—C43 | 1.392 (10) |
C5A—C4 | 1.380 (10) | C44—C45 | 1.416 (10) |
C5A—C6 | 1.396 (11) | C44—H44 | 0.9500 |
O4—H4 | 0.8400 | C1—C2 | 1.508 (10) |
C34B—C33 | 1.378 (11) | C46—H46A | 0.9900 |
C34B—C35 | 1.399 (11) | C46—H46B | 0.9900 |
C34B—H34B | 0.9500 | C26—C27 | 1.385 (12) |
C5B—C4 | 1.380 (10) | C26—C31 | 1.433 (11) |
C5B—C6 | 1.396 (11) | C26—C25 | 1.474 (12) |
C5B—H5B | 0.9500 | C32—O9 | 1.273 (9) |
O5—C9 | 1.362 (8) | C6—C7 | 1.358 (11) |
O5—C8 | 1.431 (8) | C6—H6A | 0.9500 |
O2—C1 | 1.266 (10) | C6—H6B | 0.9500 |
O14—C53 | 1.388 (9) | C17—H17A | 0.9900 |
O14—C52 | 1.435 (9) | C17—H17B | 0.9900 |
O13—C51 | 1.423 (8) | C15—C16 | 1.510 (9) |
O13—H13A | 0.8400 | C15—H15A | 0.9900 |
O8—C32 | 1.242 (9) | C15—H15B | 0.9900 |
O1—C1 | 1.280 (10) | C12—C13 | 1.377 (10) |
O1—H1 | 0.8400 | C12—H12 | 0.9500 |
O12—C40 | 1.370 (8) | C61—C60 | 1.353 (11) |
O12—C39 | 1.449 (8) | C61—H61 | 0.9500 |
O10—C38 | 1.333 (9) | C16—H16A | 0.9900 |
O10—H10A | 0.8400 | C16—H16B | 0.9900 |
N3—C50 | 1.484 (9) | C52—C51 | 1.527 (10) |
N3—C47 | 1.501 (8) | C52—H52A | 0.9900 |
N3—C48 | 1.504 (9) | C52—H52B | 0.9900 |
N3—H3 | 1.0000 | C41—C42 | 1.411 (11) |
N4—C45 | 1.425 (8) | C41—H41 | 0.9500 |
N4—C49 | 1.475 (8) | C30—C31 | 1.407 (11) |
N4—C46 | 1.481 (9) | C30—H30 | 0.9500 |
N1—C14 | 1.437 (8) | C23—C22 | 1.361 (12) |
N1—C18 | 1.460 (8) | C23—C24 | 1.371 (13) |
N1—C15 | 1.479 (8) | C23—H23 | 0.9500 |
O7—C22 | 1.343 (10) | C28—C27 | 1.401 (12) |
O7—C21 | 1.442 (9) | C28—H28 | 0.9500 |
O6—C20 | 1.410 (9) | C13—H13 | 0.9500 |
O6—H6 | 0.8400 | C58—C59 | 1.357 (12) |
O3—C3 | 1.353 (9) | C58—C57 | 1.446 (12) |
O3—H3A | 0.8400 | C58—H58 | 0.9500 |
N2—C19 | 1.496 (9) | C56—C57 | 1.372 (12) |
N2—C16 | 1.504 (8) | C56—C55 | 1.374 (14) |
N2—C17 | 1.505 (9) | C56—H56 | 0.9500 |
N2—H2 | 1.0000 | C42—C43 | 1.383 (11) |
C18—C17 | 1.525 (10) | C42—H42 | 0.9500 |
C18—H18A | 0.9900 | C4—H4A | 0.9500 |
C18—H18B | 0.9900 | C4—H4B | 0.9500 |
C14—C13 | 1.383 (10) | C37—C36 | 1.353 (12) |
C14—C9 | 1.407 (9) | C37—C38 | 1.408 (11) |
C50—C51 | 1.546 (10) | C37—H37 | 0.9500 |
C50—H50A | 0.9900 | C31—C22 | 1.428 (11) |
C50—H50B | 0.9900 | C51—H51 | 1.0000 |
C47—C46 | 1.507 (10) | C7—C2 | 1.413 (10) |
C47—H47A | 0.9900 | C7—H7 | 0.9500 |
C47—H47B | 0.9900 | C54—C55 | 1.443 (13) |
C11—C10 | 1.377 (10) | C54—H54 | 0.9500 |
C11—C12 | 1.389 (10) | C27—H27 | 0.9500 |
C11—H11 | 0.9500 | C43—H43 | 0.9500 |
C40—C41 | 1.392 (10) | C59—C60 | 1.390 (11) |
C40—C45 | 1.418 (9) | C59—H59 | 0.9500 |
C3—C4 | 1.404 (9) | C49—H49A | 0.9900 |
C3—C2 | 1.406 (10) | C49—H49B | 0.9900 |
C53—C54 | 1.374 (11) | C19—H19A | 0.9900 |
C53—C62 | 1.435 (10) | C19—H19B | 0.9900 |
C62—C61 | 1.406 (11) | C8—H8A | 0.9800 |
C62—C57 | 1.431 (10) | C8—H8B | 0.9800 |
C39—H39A | 0.9800 | C8—H8C | 0.9800 |
C39—H39B | 0.9800 | C25—C24 | 1.375 (14) |
C39—H39C | 0.9800 | C25—H25 | 0.9500 |
C9—C10 | 1.409 (9) | C21—H21A | 0.9900 |
C29—C30 | 1.388 (10) | C21—H21B | 0.9900 |
C29—C28 | 1.426 (10) | C24—H24 | 0.9500 |
C29—H29 | 0.9500 | C60—H60 | 0.9500 |
C20—C21 | 1.505 (11) | C35—C36 | 1.375 (12) |
C20—C19 | 1.519 (11) | C35—H35 | 0.9500 |
C20—H20 | 1.0000 | C35—H35A | 0.9500 |
C10—H10 | 0.9500 | C36—H36 | 0.9500 |
C48—C49 | 1.486 (10) | C55—H55 | 0.9500 |
O11—C34A—C33 | 113.9 (10) | C18—C17—H17B | 109.4 |
O11—C34A—C35 | 122.4 (10) | H17A—C17—H17B | 108.0 |
C33—C34A—C35 | 122.1 (8) | N1—C15—C16 | 110.1 (5) |
C34A—O11—H11A | 109.5 | N1—C15—H15A | 109.6 |
O4—C5A—C4 | 125.6 (8) | C16—C15—H15A | 109.6 |
O4—C5A—C6 | 113.7 (7) | N1—C15—H15B | 109.6 |
C4—C5A—C6 | 120.6 (7) | C16—C15—H15B | 109.6 |
C5A—O4—H4 | 109.5 | H15A—C15—H15B | 108.2 |
C33—C34B—C35 | 122.1 (8) | C13—C12—C11 | 119.4 (7) |
C33—C34B—H34B | 119.0 | C13—C12—H12 | 120.3 |
C35—C34B—H34B | 119.0 | C11—C12—H12 | 120.3 |
C4—C5B—C6 | 120.6 (7) | C60—C61—C62 | 120.2 (7) |
C4—C5B—H5B | 119.7 | C60—C61—H61 | 119.9 |
C6—C5B—H5B | 119.7 | C62—C61—H61 | 119.9 |
C9—O5—C8 | 117.3 (5) | N2—C16—C15 | 111.6 (5) |
C53—O14—C52 | 119.2 (6) | N2—C16—H16A | 109.3 |
C51—O13—H13A | 109.5 | C15—C16—H16A | 109.3 |
C1—O1—H1 | 109.5 | N2—C16—H16B | 109.3 |
C40—O12—C39 | 116.9 (5) | C15—C16—H16B | 109.3 |
C38—O10—H10A | 109.5 | H16A—C16—H16B | 108.0 |
C50—N3—C47 | 112.8 (5) | O14—C52—C51 | 105.4 (6) |
C50—N3—C48 | 108.6 (5) | O14—C52—H52A | 110.7 |
C47—N3—C48 | 111.4 (5) | C51—C52—H52A | 110.7 |
C50—N3—H3 | 108.0 | O14—C52—H52B | 110.7 |
C47—N3—H3 | 108.0 | C51—C52—H52B | 110.7 |
C48—N3—H3 | 108.0 | H52A—C52—H52B | 108.8 |
C45—N4—C49 | 116.0 (5) | C40—C41—C42 | 120.7 (7) |
C45—N4—C46 | 114.2 (5) | C40—C41—H41 | 119.6 |
C49—N4—C46 | 108.2 (5) | C42—C41—H41 | 119.6 |
C14—N1—C18 | 115.9 (5) | C29—C30—C31 | 121.6 (7) |
C14—N1—C15 | 114.5 (5) | C29—C30—H30 | 119.2 |
C18—N1—C15 | 109.1 (5) | C31—C30—H30 | 119.2 |
C22—O7—C21 | 119.7 (6) | C22—C23—C24 | 121.4 (9) |
C20—O6—H6 | 109.5 | C22—C23—H23 | 119.3 |
C3—O3—H3A | 109.5 | C24—C23—H23 | 119.3 |
C19—N2—C16 | 112.1 (6) | C27—C28—C29 | 119.0 (8) |
C19—N2—C17 | 108.9 (5) | C27—C28—H28 | 120.5 |
C16—N2—C17 | 111.3 (5) | C29—C28—H28 | 120.5 |
C19—N2—H2 | 108.1 | C12—C13—C14 | 121.6 (6) |
C16—N2—H2 | 108.1 | C12—C13—H13 | 119.2 |
C17—N2—H2 | 108.1 | C14—C13—H13 | 119.2 |
N1—C18—C17 | 109.6 (6) | C59—C58—C57 | 122.2 (7) |
N1—C18—H18A | 109.7 | C59—C58—H58 | 118.9 |
C17—C18—H18A | 109.7 | C57—C58—H58 | 118.9 |
N1—C18—H18B | 109.7 | C57—C56—C55 | 121.0 (8) |
C17—C18—H18B | 109.7 | C57—C56—H56 | 119.5 |
H18A—C18—H18B | 108.2 | C55—C56—H56 | 119.5 |
C13—C14—C9 | 119.1 (6) | C56—C57—C62 | 120.0 (8) |
C13—C14—N1 | 122.8 (6) | C56—C57—C58 | 124.0 (7) |
C9—C14—N1 | 118.1 (6) | C62—C57—C58 | 115.9 (7) |
N3—C50—C51 | 111.9 (5) | C43—C42—C41 | 119.5 (7) |
N3—C50—H50A | 109.2 | C43—C42—H42 | 120.2 |
C51—C50—H50A | 109.2 | C41—C42—H42 | 120.2 |
N3—C50—H50B | 109.2 | C5B—C4—C3 | 119.4 (7) |
C51—C50—H50B | 109.2 | C5A—C4—C3 | 119.4 (7) |
H50A—C50—H50B | 107.9 | C5A—C4—H4A | 120.3 |
N3—C47—C46 | 112.5 (6) | C3—C4—H4A | 120.3 |
N3—C47—H47A | 109.1 | C5B—C4—H4B | 120.3 |
C46—C47—H47A | 109.1 | C3—C4—H4B | 120.3 |
N3—C47—H47B | 109.1 | C36—C37—C38 | 120.1 (7) |
C46—C47—H47B | 109.1 | C36—C37—H37 | 120.0 |
H47A—C47—H47B | 107.8 | C38—C37—H37 | 120.0 |
C10—C11—C12 | 120.5 (6) | C30—C31—C22 | 122.5 (7) |
C10—C11—H11 | 119.7 | C30—C31—C26 | 118.1 (7) |
C12—C11—H11 | 119.7 | C22—C31—C26 | 119.4 (8) |
O12—C40—C41 | 124.3 (6) | O13—C51—C52 | 114.0 (6) |
O12—C40—C45 | 115.9 (6) | O13—C51—C50 | 111.3 (6) |
C41—C40—C45 | 119.8 (7) | C52—C51—C50 | 108.3 (6) |
O3—C3—C4 | 117.7 (6) | O13—C51—H51 | 107.7 |
O3—C3—C2 | 121.8 (6) | C52—C51—H51 | 107.7 |
C4—C3—C2 | 120.5 (6) | C50—C51—H51 | 107.7 |
C54—C53—O14 | 123.7 (7) | C6—C7—C2 | 121.1 (7) |
C54—C53—C62 | 122.9 (7) | C6—C7—H7 | 119.4 |
O14—C53—C62 | 113.5 (6) | C2—C7—H7 | 119.4 |
C61—C62—C57 | 120.2 (7) | O10—C38—C33 | 121.9 (7) |
C61—C62—C53 | 122.3 (6) | O10—C38—C37 | 118.9 (7) |
C57—C62—C53 | 117.4 (7) | C33—C38—C37 | 119.2 (7) |
O12—C39—H39A | 109.5 | C53—C54—C55 | 116.4 (8) |
O12—C39—H39B | 109.5 | C53—C54—H54 | 121.8 |
H39A—C39—H39B | 109.5 | C55—C54—H54 | 121.8 |
O12—C39—H39C | 109.5 | C26—C27—C28 | 121.2 (8) |
H39A—C39—H39C | 109.5 | C26—C27—H27 | 119.4 |
H39B—C39—H39C | 109.5 | C28—C27—H27 | 119.4 |
O5—C9—C14 | 116.9 (6) | O7—C22—C23 | 125.3 (8) |
O5—C9—C10 | 124.0 (6) | O7—C22—C31 | 114.0 (7) |
C14—C9—C10 | 119.0 (6) | C23—C22—C31 | 120.7 (8) |
C30—C29—C28 | 119.8 (8) | C3—C2—C7 | 118.1 (6) |
C30—C29—H29 | 120.1 | C3—C2—C1 | 120.9 (7) |
C28—C29—H29 | 120.1 | C7—C2—C1 | 121.0 (7) |
O6—C20—C21 | 110.7 (6) | C42—C43—C44 | 120.7 (7) |
O6—C20—C19 | 110.9 (6) | C42—C43—H43 | 119.7 |
C21—C20—C19 | 111.1 (7) | C44—C43—H43 | 119.7 |
O6—C20—H20 | 108.0 | C58—C59—C60 | 119.3 (8) |
C21—C20—H20 | 108.0 | C58—C59—H59 | 120.4 |
C19—C20—H20 | 108.0 | C60—C59—H59 | 120.4 |
C11—C10—C9 | 120.2 (6) | N4—C49—C48 | 109.7 (6) |
C11—C10—H10 | 119.9 | N4—C49—H49A | 109.7 |
C9—C10—H10 | 119.9 | C48—C49—H49A | 109.7 |
C49—C48—N3 | 112.6 (5) | N4—C49—H49B | 109.7 |
C49—C48—H48A | 109.1 | C48—C49—H49B | 109.7 |
N3—C48—H48A | 109.1 | H49A—C49—H49B | 108.2 |
C49—C48—H48B | 109.1 | N2—C19—C20 | 115.0 (6) |
N3—C48—H48B | 109.1 | N2—C19—H19A | 108.5 |
H48A—C48—H48B | 107.8 | C20—C19—H19A | 108.5 |
C34B—C33—C38 | 118.8 (7) | N2—C19—H19B | 108.5 |
C34A—C33—C38 | 118.8 (7) | C20—C19—H19B | 108.5 |
C34B—C33—C32 | 120.4 (7) | H19A—C19—H19B | 107.5 |
C34A—C33—C32 | 120.4 (7) | O5—C8—H8A | 109.5 |
C38—C33—C32 | 120.7 (7) | O5—C8—H8B | 109.5 |
C43—C44—C45 | 120.5 (7) | H8A—C8—H8B | 109.5 |
C43—C44—H44 | 119.7 | O5—C8—H8C | 109.5 |
C45—C44—H44 | 119.7 | H8A—C8—H8C | 109.5 |
O2—C1—O1 | 124.4 (7) | H8B—C8—H8C | 109.5 |
O2—C1—C2 | 118.4 (7) | C24—C25—C26 | 119.8 (8) |
O1—C1—C2 | 117.2 (8) | C24—C25—H25 | 120.1 |
N4—C46—C47 | 109.6 (5) | C26—C25—H25 | 120.1 |
N4—C46—H46A | 109.7 | O7—C21—C20 | 107.1 (6) |
C47—C46—H46A | 109.7 | O7—C21—H21A | 110.3 |
N4—C46—H46B | 109.7 | C20—C21—H21A | 110.3 |
C47—C46—H46B | 109.7 | O7—C21—H21B | 110.3 |
H46A—C46—H46B | 108.2 | C20—C21—H21B | 110.3 |
C27—C26—C31 | 120.3 (8) | H21A—C21—H21B | 108.6 |
C27—C26—C25 | 122.6 (8) | C23—C24—C25 | 121.7 (9) |
C31—C26—C25 | 116.9 (8) | C23—C24—H24 | 119.2 |
O8—C32—O9 | 123.1 (7) | C25—C24—H24 | 119.2 |
O8—C32—C33 | 118.9 (7) | C61—C60—C59 | 122.1 (8) |
O9—C32—C33 | 118.0 (7) | C61—C60—H60 | 119.0 |
C44—C45—C40 | 118.7 (6) | C59—C60—H60 | 119.0 |
C44—C45—N4 | 123.0 (6) | C36—C35—C34A | 117.6 (8) |
C40—C45—N4 | 118.3 (6) | C36—C35—C34B | 117.6 (8) |
C7—C6—C5A | 120.3 (7) | C36—C35—H35 | 121.2 |
C7—C6—C5B | 120.3 (7) | C34A—C35—H35 | 121.2 |
C7—C6—H6A | 119.8 | C36—C35—H35A | 121.2 |
C5A—C6—H6A | 119.8 | C34B—C35—H35A | 121.2 |
C7—C6—H6B | 119.8 | C37—C36—C35 | 122.2 (7) |
C5B—C6—H6B | 119.8 | C37—C36—H36 | 118.9 |
N2—C17—C18 | 111.3 (5) | C35—C36—H36 | 118.9 |
N2—C17—H17A | 109.4 | C56—C55—C54 | 121.8 (8) |
C18—C17—H17A | 109.4 | C56—C55—H55 | 119.1 |
N2—C17—H17B | 109.4 | C54—C55—H55 | 119.1 |
C31H34N2O7 | F(000) = 1160 |
Mr = 546.60 | Dx = 1.359 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.319 (2) Å | Cell parameters from 9874 reflections |
b = 17.672 (4) Å | θ = 2.6–26.4° |
c = 13.391 (3) Å | µ = 0.10 mm−1 |
β = 93.90 (3)° | T = 100 K |
V = 2672.4 (10) Å3 | Plate, colourless |
Z = 4 |
Bruker APEX-II CCD diffractometer | Rint = 0.040 |
φ and ω scans | θmax = 26.3°, θmin = 2.3° |
48278 measured reflections | h = −13→14 |
5387 independent reflections | k = −22→22 |
4822 reflections with I > 2σ(I) | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.154 | w = 1/[σ2(Fo2) + 4.1944P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max < 0.001 |
5387 reflections | Δρmax = 0.28 e Å−3 |
395 parameters | Δρmin = −0.33 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C4A | 0.5187 (3) | −0.02832 (16) | 0.3486 (2) | 0.0411 (7) | 0.46 |
C5A | 0.4080 (3) | −0.04162 (16) | 0.30503 (19) | 0.0411 (7) | 0.2 |
C7A | 0.3438 (3) | 0.07984 (17) | 0.3574 (2) | 0.0474 (8) | 0.34 |
O4 | 0.6059 (4) | −0.0740 (2) | 0.3477 (3) | 0.0340 (9) | 0.46 |
H4 | 0.586377 | −0.116002 | 0.370894 | 0.051* | 0.46 |
O5 | 0.3619 (9) | −0.0998 (5) | 0.2494 (7) | 0.038 (2) | 0.2 |
H5 | 0.401053 | −0.139298 | 0.263017 | 0.057* | 0.2 |
O6 | 0.2819 (6) | 0.1301 (4) | 0.3540 (6) | 0.059 (2) | 0.34 |
H6 | 0.266037 | 0.142401 | 0.293955 | 0.089* | 0.34 |
C4B | 0.5187 (3) | −0.02832 (16) | 0.3486 (2) | 0.0411 (7) | 0.54 |
H4B | 0.578667 | −0.065744 | 0.345850 | 0.049* | 0.54 |
C5B | 0.4080 (3) | −0.04162 (16) | 0.30503 (19) | 0.0411 (7) | 0.8 |
H5B | 0.391535 | −0.088433 | 0.272075 | 0.049* | 0.8 |
C7B | 0.3438 (3) | 0.07984 (17) | 0.3574 (2) | 0.0474 (8) | 0.66 |
H7B | 0.282928 | 0.116658 | 0.359795 | 0.057* | 0.66 |
O7 | 0.20012 (17) | 0.56045 (10) | 0.54541 (14) | 0.0365 (4) | |
O9 | 0.78811 (19) | 0.24065 (11) | 0.68841 (15) | 0.0455 (5) | |
O8 | 0.5420 (2) | 0.23210 (11) | 0.69615 (17) | 0.0512 (6) | |
H8 | 0.556801 | 0.210199 | 0.642743 | 0.077* | |
O2 | 0.5842 (2) | 0.17546 (12) | 0.50400 (17) | 0.0555 (6) | |
O1 | 0.3999 (2) | 0.21524 (12) | 0.46590 (17) | 0.0553 (6) | |
N006 | 0.3099 (2) | 0.44637 (12) | 0.45642 (15) | 0.0321 (5) | |
O3 | 0.6558 (2) | 0.05055 (15) | 0.43765 (17) | 0.0583 (6) | |
H3 | 0.661385 | 0.092684 | 0.466615 | 0.087* | |
N008 | 0.4882 (2) | 0.34663 (12) | 0.54758 (16) | 0.0328 (5) | |
C9 | 0.1498 (2) | 0.53952 (14) | 0.45343 (19) | 0.0321 (6) | |
C18 | 0.4010 (3) | 0.38696 (14) | 0.60742 (19) | 0.0346 (6) | |
H18A | 0.435713 | 0.435465 | 0.632029 | 0.041* | |
H18B | 0.384470 | 0.355838 | 0.666332 | 0.041* | |
C14 | 0.2069 (2) | 0.47945 (14) | 0.40602 (19) | 0.0322 (6) | |
C10 | 0.0518 (2) | 0.57447 (15) | 0.4054 (2) | 0.0359 (6) | |
H10 | 0.013420 | 0.614579 | 0.437629 | 0.043* | |
C32 | 0.9586 (3) | 0.19015 (15) | 0.6247 (2) | 0.0358 (6) | |
C20 | 0.6066 (3) | 0.34001 (14) | 0.6025 (2) | 0.0359 (6) | |
H20A | 0.640345 | 0.391354 | 0.612506 | 0.043* | |
H20B | 0.659696 | 0.311274 | 0.560642 | 0.043* | |
C31 | 0.8879 (3) | 0.14879 (16) | 0.5530 (2) | 0.0370 (6) | |
H31 | 0.804070 | 0.152649 | 0.551928 | 0.044* | |
C19 | 0.2865 (3) | 0.40245 (15) | 0.5465 (2) | 0.0352 (6) | |
H19A | 0.247849 | 0.353981 | 0.526587 | 0.042* | |
H19B | 0.232198 | 0.431096 | 0.587386 | 0.042* | |
C13 | 0.1627 (3) | 0.45759 (15) | 0.3110 (2) | 0.0376 (6) | |
H13 | 0.200277 | 0.417523 | 0.278045 | 0.045* | |
C17 | 0.5011 (3) | 0.38562 (15) | 0.44915 (19) | 0.0360 (6) | |
H17A | 0.549921 | 0.353819 | 0.407134 | 0.043* | |
H17B | 0.542841 | 0.434335 | 0.461204 | 0.043* | |
C16 | 0.3830 (3) | 0.40019 (16) | 0.3940 (2) | 0.0376 (6) | |
C50 | 0.1437 (3) | 0.62123 (16) | 0.5953 (2) | 0.0407 (7) | |
H50A | 0.142039 | 0.666526 | 0.553029 | 0.061* | |
H50B | 0.188073 | 0.632029 | 0.659126 | 0.061* | |
H50C | 0.062518 | 0.606571 | 0.607827 | 0.061* | |
C23 | 0.9088 (3) | 0.23499 (14) | 0.6993 (2) | 0.0399 (7) | |
C12 | 0.0646 (3) | 0.49288 (16) | 0.2627 (2) | 0.0392 (6) | |
H12 | 0.035894 | 0.477135 | 0.197692 | 0.047* | |
C6 | 0.3196 (3) | 0.01198 (17) | 0.3083 (2) | 0.0450 (7) | |
H6A | 0.243124 | 0.002470 | 0.277205 | 0.054* | 0.2 |
H6B | 0.243124 | 0.002470 | 0.277205 | 0.054* | 0.8 |
C11 | 0.0095 (3) | 0.55111 (15) | 0.3106 (2) | 0.0397 (6) | |
H11 | −0.057679 | 0.575296 | 0.278383 | 0.048* | |
C27 | 1.0841 (3) | 0.18537 (16) | 0.6242 (2) | 0.0409 (7) | |
C3 | 0.5439 (3) | 0.04095 (18) | 0.3974 (2) | 0.0435 (7) | |
C30 | 0.9384 (3) | 0.10314 (18) | 0.4850 (2) | 0.0416 (7) | |
H30 | 0.889503 | 0.074362 | 0.438671 | 0.050* | |
C1 | 0.4807 (4) | 0.16710 (18) | 0.4609 (2) | 0.0516 (9) | |
C21 | 0.6047 (3) | 0.30127 (15) | 0.7039 (2) | 0.0412 (7) | |
H21 | 0.561191 | 0.335295 | 0.748504 | 0.049* | |
C2 | 0.4559 (3) | 0.09537 (15) | 0.4034 (2) | 0.0422 (7) | |
C22 | 0.7286 (3) | 0.29203 (16) | 0.7507 (2) | 0.0461 (8) | |
H22A | 0.769889 | 0.341437 | 0.754354 | 0.055* | |
H22B | 0.726720 | 0.271421 | 0.819359 | 0.055* | |
C29 | 1.0625 (3) | 0.09876 (18) | 0.4836 (2) | 0.0446 (7) | |
H29 | 1.097303 | 0.067438 | 0.435964 | 0.054* | |
C26 | 1.1551 (3) | 0.22348 (17) | 0.7003 (3) | 0.0526 (8) | |
H26 | 1.238965 | 0.222855 | 0.699418 | 0.063* | |
C28 | 1.1331 (3) | 0.13972 (18) | 0.5510 (2) | 0.0461 (7) | |
H28 | 1.216643 | 0.137341 | 0.548371 | 0.055* | |
C24 | 0.9783 (3) | 0.26783 (16) | 0.7754 (2) | 0.0510 (8) | |
H24 | 0.943506 | 0.294598 | 0.827523 | 0.061* | |
C25 | 1.1023 (4) | 0.26095 (17) | 0.7747 (3) | 0.0587 (9) | |
H25 | 1.150763 | 0.283076 | 0.827569 | 0.070* | |
H16A | 0.341 (3) | 0.349 (2) | 0.376 (3) | 0.070* | |
H16B | 0.400 (3) | 0.429 (2) | 0.336 (3) | 0.070* | |
H008 | 0.459 (3) | 0.2996 (19) | 0.533 (2) | 0.043 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C4A | 0.0582 (19) | 0.0369 (15) | 0.0289 (13) | −0.0028 (14) | 0.0093 (13) | −0.0013 (11) |
C5A | 0.065 (2) | 0.0336 (14) | 0.0252 (13) | −0.0133 (14) | 0.0049 (13) | −0.0002 (11) |
C7A | 0.074 (2) | 0.0360 (16) | 0.0326 (15) | −0.0103 (16) | 0.0035 (14) | 0.0035 (12) |
O4 | 0.041 (2) | 0.030 (2) | 0.031 (2) | 0.0090 (18) | 0.0044 (17) | −0.0016 (17) |
O5 | 0.056 (6) | 0.023 (4) | 0.034 (5) | 0.000 (4) | 0.002 (4) | −0.002 (4) |
O6 | 0.047 (4) | 0.056 (4) | 0.073 (5) | 0.037 (3) | −0.008 (4) | −0.020 (4) |
C4B | 0.0582 (19) | 0.0369 (15) | 0.0289 (13) | −0.0028 (14) | 0.0093 (13) | −0.0013 (11) |
C5B | 0.065 (2) | 0.0336 (14) | 0.0252 (13) | −0.0133 (14) | 0.0049 (13) | −0.0002 (11) |
C7B | 0.074 (2) | 0.0360 (16) | 0.0326 (15) | −0.0103 (16) | 0.0035 (14) | 0.0035 (12) |
O7 | 0.0459 (11) | 0.0289 (9) | 0.0356 (10) | 0.0049 (8) | 0.0086 (8) | −0.0076 (8) |
O9 | 0.0570 (14) | 0.0340 (11) | 0.0457 (12) | 0.0086 (9) | 0.0062 (10) | −0.0101 (9) |
O8 | 0.0760 (16) | 0.0260 (10) | 0.0541 (13) | 0.0049 (10) | 0.0231 (12) | 0.0084 (9) |
O2 | 0.0691 (16) | 0.0429 (12) | 0.0570 (14) | −0.0210 (11) | 0.0220 (12) | −0.0202 (11) |
O1 | 0.0845 (18) | 0.0283 (11) | 0.0546 (14) | −0.0044 (11) | 0.0157 (12) | −0.0047 (10) |
N006 | 0.0433 (13) | 0.0253 (11) | 0.0290 (11) | 0.0037 (9) | 0.0129 (9) | 0.0002 (9) |
O3 | 0.0566 (14) | 0.0678 (16) | 0.0520 (13) | −0.0161 (12) | 0.0139 (11) | −0.0264 (12) |
N008 | 0.0494 (14) | 0.0188 (10) | 0.0318 (11) | 0.0035 (9) | 0.0150 (10) | 0.0015 (9) |
C9 | 0.0377 (14) | 0.0245 (12) | 0.0352 (13) | −0.0044 (10) | 0.0101 (11) | −0.0010 (10) |
C18 | 0.0505 (17) | 0.0240 (12) | 0.0312 (13) | 0.0060 (11) | 0.0176 (12) | 0.0017 (10) |
C14 | 0.0404 (15) | 0.0235 (12) | 0.0338 (13) | −0.0017 (11) | 0.0109 (11) | 0.0011 (10) |
C10 | 0.0394 (15) | 0.0241 (12) | 0.0454 (15) | −0.0022 (11) | 0.0113 (12) | 0.0006 (11) |
C32 | 0.0473 (16) | 0.0252 (13) | 0.0348 (14) | 0.0026 (11) | 0.0022 (12) | 0.0108 (11) |
C20 | 0.0497 (17) | 0.0217 (12) | 0.0376 (14) | 0.0027 (11) | 0.0127 (12) | −0.0004 (10) |
C31 | 0.0409 (15) | 0.0377 (15) | 0.0324 (13) | 0.0064 (12) | 0.0016 (11) | 0.0050 (11) |
C19 | 0.0476 (16) | 0.0249 (12) | 0.0352 (14) | 0.0007 (11) | 0.0173 (12) | 0.0009 (11) |
C13 | 0.0516 (17) | 0.0261 (13) | 0.0363 (14) | −0.0029 (12) | 0.0130 (12) | −0.0027 (11) |
C17 | 0.0530 (17) | 0.0253 (12) | 0.0321 (13) | 0.0046 (12) | 0.0209 (12) | 0.0029 (10) |
C16 | 0.0520 (17) | 0.0306 (14) | 0.0318 (14) | 0.0055 (12) | 0.0155 (12) | −0.0010 (11) |
C50 | 0.0509 (17) | 0.0300 (14) | 0.0425 (16) | 0.0062 (12) | 0.0130 (13) | −0.0080 (12) |
C23 | 0.0584 (19) | 0.0192 (12) | 0.0420 (15) | 0.0010 (12) | 0.0018 (13) | 0.0047 (11) |
C12 | 0.0480 (17) | 0.0327 (14) | 0.0370 (15) | −0.0087 (12) | 0.0036 (12) | 0.0015 (12) |
C6 | 0.0600 (19) | 0.0423 (16) | 0.0326 (14) | −0.0063 (14) | 0.0009 (13) | 0.0019 (12) |
C11 | 0.0434 (16) | 0.0294 (14) | 0.0464 (16) | −0.0075 (12) | 0.0043 (13) | 0.0066 (12) |
C27 | 0.0471 (17) | 0.0290 (14) | 0.0460 (16) | −0.0038 (12) | −0.0008 (13) | 0.0162 (12) |
C3 | 0.0550 (18) | 0.0487 (17) | 0.0279 (13) | −0.0227 (15) | 0.0111 (12) | −0.0069 (12) |
C30 | 0.0436 (16) | 0.0482 (17) | 0.0329 (14) | 0.0065 (13) | 0.0029 (12) | 0.0020 (12) |
C1 | 0.083 (3) | 0.0378 (17) | 0.0363 (16) | −0.0258 (17) | 0.0226 (16) | −0.0044 (13) |
C21 | 0.065 (2) | 0.0226 (13) | 0.0373 (15) | 0.0108 (13) | 0.0156 (14) | 0.0012 (11) |
C2 | 0.070 (2) | 0.0271 (13) | 0.0312 (14) | −0.0112 (13) | 0.0179 (14) | −0.0009 (11) |
C22 | 0.076 (2) | 0.0262 (14) | 0.0374 (15) | 0.0125 (14) | 0.0092 (15) | −0.0024 (12) |
C29 | 0.0472 (17) | 0.0517 (18) | 0.0359 (15) | 0.0092 (14) | 0.0095 (13) | 0.0078 (13) |
C26 | 0.056 (2) | 0.0315 (15) | 0.069 (2) | −0.0108 (14) | −0.0061 (17) | 0.0098 (15) |
C28 | 0.0395 (16) | 0.0495 (18) | 0.0502 (18) | 0.0025 (14) | 0.0082 (14) | 0.0178 (15) |
C24 | 0.078 (2) | 0.0235 (14) | 0.0505 (18) | −0.0013 (14) | −0.0028 (16) | −0.0018 (13) |
C25 | 0.075 (3) | 0.0274 (15) | 0.072 (2) | −0.0128 (15) | −0.0123 (19) | −0.0025 (15) |
C4A—O4 | 1.275 (5) | C32—C31 | 1.411 (4) |
C4A—C5A | 1.366 (4) | C32—C27 | 1.423 (4) |
C4A—C3 | 1.408 (4) | C32—C23 | 1.422 (4) |
C5A—O5 | 1.354 (9) | C20—C21 | 1.522 (4) |
C5A—C6 | 1.380 (4) | C20—H20A | 0.9900 |
C7A—O6 | 1.130 (6) | C20—H20B | 0.9900 |
C7A—C6 | 1.386 (4) | C31—C30 | 1.370 (4) |
C7A—C2 | 1.399 (5) | C31—H31 | 0.9500 |
O4—H4 | 0.8400 | C19—H19A | 0.9900 |
O5—H5 | 0.8400 | C19—H19B | 0.9900 |
O6—H6 | 0.8400 | C13—C12 | 1.393 (4) |
C4B—C5B | 1.366 (4) | C13—H13 | 0.9500 |
C4B—C3 | 1.408 (4) | C17—C16 | 1.505 (4) |
C4B—H4B | 0.9500 | C17—H17A | 0.9900 |
C5B—C6 | 1.380 (4) | C17—H17B | 0.9900 |
C5B—H5B | 0.9500 | C16—H16A | 1.04 (4) |
C7B—C6 | 1.386 (4) | C16—H16B | 0.96 (4) |
C7B—C2 | 1.399 (5) | C50—H50A | 0.9800 |
C7B—H7B | 0.9500 | C50—H50B | 0.9800 |
O7—C9 | 1.372 (3) | C50—H50C | 0.9800 |
O7—C50 | 1.437 (3) | C23—C24 | 1.374 (4) |
O9—C23 | 1.367 (4) | C12—C11 | 1.383 (4) |
O9—C22 | 1.432 (3) | C12—H12 | 0.9500 |
O8—C21 | 1.413 (4) | C6—H6A | 0.9500 |
O8—H8 | 0.8400 | C6—H6B | 0.9500 |
O2—C1 | 1.280 (4) | C11—H11 | 0.9500 |
O1—C1 | 1.254 (4) | C27—C28 | 1.412 (4) |
N006—C14 | 1.431 (3) | C27—C26 | 1.424 (4) |
N006—C16 | 1.465 (3) | C3—C2 | 1.391 (5) |
N006—C19 | 1.473 (3) | C30—C29 | 1.409 (4) |
O3—C3 | 1.354 (4) | C30—H30 | 0.9500 |
O3—H3 | 0.8400 | C1—C2 | 1.500 (4) |
N008—C20 | 1.489 (4) | C21—C22 | 1.505 (5) |
N008—C18 | 1.494 (3) | C21—H21 | 1.0000 |
N008—C17 | 1.503 (3) | C22—H22A | 0.9900 |
N008—H008 | 0.91 (3) | C22—H22B | 0.9900 |
C9—C10 | 1.389 (4) | C29—C28 | 1.370 (5) |
C9—C14 | 1.416 (4) | C29—H29 | 0.9500 |
C18—C19 | 1.509 (4) | C26—C25 | 1.367 (5) |
C18—H18A | 0.9900 | C26—H26 | 0.9500 |
C18—H18B | 0.9900 | C28—H28 | 0.9500 |
C14—C13 | 1.391 (4) | C24—C25 | 1.410 (5) |
C10—C11 | 1.389 (4) | C24—H24 | 0.9500 |
C10—H10 | 0.9500 | C25—H25 | 0.9500 |
O4—C4A—C5A | 125.1 (3) | H17A—C17—H17B | 107.9 |
O4—C4A—C3 | 115.0 (3) | N006—C16—C17 | 109.4 (2) |
C5A—C4A—C3 | 119.9 (3) | N006—C16—H16A | 110 (2) |
O5—C5A—C4A | 132.4 (5) | C17—C16—H16A | 110 (2) |
O5—C5A—C6 | 106.6 (5) | N006—C16—H16B | 108 (2) |
C4A—C5A—C6 | 120.9 (3) | C17—C16—H16B | 106 (2) |
O6—C7A—C6 | 124.0 (5) | H16A—C16—H16B | 113 (3) |
O6—C7A—C2 | 113.9 (5) | O7—C50—H50A | 109.5 |
C6—C7A—C2 | 121.5 (3) | O7—C50—H50B | 109.5 |
C4A—O4—H4 | 109.5 | H50A—C50—H50B | 109.5 |
C5A—O5—H5 | 109.5 | O7—C50—H50C | 109.5 |
C7A—O6—H6 | 109.5 | H50A—C50—H50C | 109.5 |
C5B—C4B—C3 | 119.9 (3) | H50B—C50—H50C | 109.5 |
C5B—C4B—H4B | 120.1 | O9—C23—C24 | 124.4 (3) |
C3—C4B—H4B | 120.1 | O9—C23—C32 | 114.0 (3) |
C4B—C5B—C6 | 120.9 (3) | C24—C23—C32 | 121.5 (3) |
C4B—C5B—H5B | 119.5 | C11—C12—C13 | 119.2 (3) |
C6—C5B—H5B | 119.5 | C11—C12—H12 | 120.4 |
C6—C7B—C2 | 121.5 (3) | C13—C12—H12 | 120.4 |
C6—C7B—H7B | 119.2 | C5B—C6—C7B | 119.3 (3) |
C2—C7B—H7B | 119.2 | C5A—C6—C7A | 119.3 (3) |
C9—O7—C50 | 116.6 (2) | C5A—C6—H6A | 120.4 |
C23—O9—C22 | 119.4 (2) | C7A—C6—H6A | 120.4 |
C21—O8—H8 | 109.5 | C5B—C6—H6B | 120.4 |
C14—N006—C16 | 115.6 (2) | C7B—C6—H6B | 120.4 |
C14—N006—C19 | 114.6 (2) | C12—C11—C10 | 120.5 (3) |
C16—N006—C19 | 108.3 (2) | C12—C11—H11 | 119.8 |
C3—O3—H3 | 109.5 | C10—C11—H11 | 119.8 |
C20—N008—C18 | 112.2 (2) | C28—C27—C32 | 118.4 (3) |
C20—N008—C17 | 109.4 (2) | C28—C27—C26 | 122.6 (3) |
C18—N008—C17 | 111.02 (19) | C32—C27—C26 | 118.9 (3) |
C20—N008—H008 | 109 (2) | O3—C3—C2 | 123.0 (3) |
C18—N008—H008 | 108 (2) | O3—C3—C4B | 116.6 (3) |
C17—N008—H008 | 106 (2) | C2—C3—C4B | 120.3 (3) |
O7—C9—C10 | 124.4 (2) | O3—C3—C4A | 116.6 (3) |
O7—C9—C14 | 115.5 (2) | C2—C3—C4A | 120.3 (3) |
C10—C9—C14 | 120.1 (2) | C31—C30—C29 | 120.2 (3) |
N008—C18—C19 | 111.8 (2) | C31—C30—H30 | 119.9 |
N008—C18—H18A | 109.3 | C29—C30—H30 | 119.9 |
C19—C18—H18A | 109.3 | O1—C1—O2 | 123.1 (3) |
N008—C18—H18B | 109.3 | O1—C1—C2 | 119.3 (3) |
C19—C18—H18B | 109.3 | O2—C1—C2 | 117.6 (3) |
H18A—C18—H18B | 107.9 | O8—C21—C22 | 112.7 (2) |
C13—C14—C9 | 118.1 (3) | O8—C21—C20 | 111.1 (2) |
C13—C14—N006 | 123.3 (2) | C22—C21—C20 | 110.5 (3) |
C9—C14—N006 | 118.5 (2) | O8—C21—H21 | 107.4 |
C9—C10—C11 | 120.4 (3) | C22—C21—H21 | 107.4 |
C9—C10—H10 | 119.8 | C20—C21—H21 | 107.4 |
C11—C10—H10 | 119.8 | C3—C2—C7A | 118.1 (3) |
C31—C32—C27 | 119.1 (3) | C3—C2—C7B | 118.1 (3) |
C31—C32—C23 | 122.2 (3) | C3—C2—C1 | 120.3 (3) |
C27—C32—C23 | 118.7 (3) | C7A—C2—C1 | 121.6 (3) |
N008—C20—C21 | 114.2 (2) | C7B—C2—C1 | 121.6 (3) |
N008—C20—H20A | 108.7 | O9—C22—C21 | 106.7 (2) |
C21—C20—H20A | 108.7 | O9—C22—H22A | 110.4 |
N008—C20—H20B | 108.7 | C21—C22—H22A | 110.4 |
C21—C20—H20B | 108.7 | O9—C22—H22B | 110.4 |
H20A—C20—H20B | 107.6 | C21—C22—H22B | 110.4 |
C30—C31—C32 | 120.9 (3) | H22A—C22—H22B | 108.6 |
C30—C31—H31 | 119.5 | C28—C29—C30 | 120.0 (3) |
C32—C31—H31 | 119.5 | C28—C29—H29 | 120.0 |
N006—C19—C18 | 110.1 (2) | C30—C29—H29 | 120.0 |
N006—C19—H19A | 109.6 | C25—C26—C27 | 119.8 (3) |
C18—C19—H19A | 109.6 | C25—C26—H26 | 120.1 |
N006—C19—H19B | 109.6 | C27—C26—H26 | 120.1 |
C18—C19—H19B | 109.6 | C29—C28—C27 | 121.4 (3) |
H19A—C19—H19B | 108.2 | C29—C28—H28 | 119.3 |
C14—C13—C12 | 121.8 (3) | C27—C28—H28 | 119.3 |
C14—C13—H13 | 119.1 | C23—C24—C25 | 118.6 (3) |
C12—C13—H13 | 119.1 | C23—C24—H24 | 120.7 |
N008—C17—C16 | 111.9 (2) | C25—C24—H24 | 120.7 |
N008—C17—H17A | 109.2 | C26—C25—C24 | 122.1 (3) |
C16—C17—H17A | 109.2 | C26—C25—H25 | 118.9 |
N008—C17—H17B | 109.2 | C24—C25—H25 | 118.9 |
C16—C17—H17B | 109.2 |
C31.10H33.33N2O6.35 | F(000) = 1139 |
Mr = 536.73 | Dx = 1.360 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.153 (4) Å | Cell parameters from 9884 reflections |
b = 17.701 (5) Å | θ = 2.8–30.5° |
c = 13.336 (4) Å | µ = 0.10 mm−1 |
β = 95.232 (17)° | T = 100 K |
V = 2621.8 (13) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.1 × 0.1 mm |
Bruker APEX-II CCD diffractometer | 6429 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.055 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0731 before and 0.0582 after correction. The Ratio of minimum to maximum transmission is 0.9337. The λ/2 correction factor is Not present. | θmax = 30.4°, θmin = 2.6° |
Tmin = 0.697, Tmax = 0.746 | h = −15→15 |
63397 measured reflections | k = −25→25 |
7929 independent reflections | l = −18→18 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.176 | w = 1/[σ2(Fo2) + (0.062P)2 + 2.3743P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
7929 reflections | Δρmax = 0.67 e Å−3 |
378 parameters | Δρmin = −0.50 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C3A | 0.54897 (19) | 0.04364 (11) | 0.39813 (15) | 0.0304 (4) | 0.77 |
C4A | 0.5229 (2) | −0.02492 (11) | 0.34726 (15) | 0.0275 (4) | 0.35 |
C5A | 0.4079 (2) | −0.04010 (11) | 0.30555 (15) | 0.0276 (4) | 0.23 |
O3 | 0.66037 (17) | 0.05453 (12) | 0.43448 (16) | 0.0333 (4) | 0.77 |
H3 | 0.666368 | 0.096033 | 0.461798 | 0.050* | 0.77 |
O4 | 0.6121 (4) | −0.0733 (3) | 0.3464 (4) | 0.0353 (10) | 0.35 |
H4 | 0.587819 | −0.112209 | 0.318048 | 0.053* | 0.35 |
O5 | 0.3642 (8) | −0.0983 (5) | 0.2468 (6) | 0.048 (2) | 0.23 |
H5 | 0.419270 | −0.127284 | 0.236966 | 0.072* | 0.23 |
C3B | 0.54897 (19) | 0.04364 (11) | 0.39813 (15) | 0.0304 (4) | 0.33 |
H3B | 0.626849 | 0.053681 | 0.425955 | 0.036* | 0.33 |
C4B | 0.5229 (2) | −0.02492 (11) | 0.34726 (15) | 0.0275 (4) | 0.65 |
H4B | 0.583768 | −0.060195 | 0.341767 | 0.033* | 0.65 |
C5B | 0.4079 (2) | −0.04010 (11) | 0.30555 (15) | 0.0276 (4) | 0.77 |
H5B | 0.391656 | −0.085620 | 0.272212 | 0.033* | 0.77 |
O6 | 0.19885 (12) | 0.55858 (7) | 0.54809 (10) | 0.0239 (3) | |
O8 | 0.79943 (13) | 0.23889 (8) | 0.69484 (11) | 0.0273 (3) | |
O7 | 0.55028 (15) | 0.23028 (8) | 0.70171 (13) | 0.0310 (3) | |
O1 | 0.40007 (14) | 0.21532 (8) | 0.47165 (12) | 0.0302 (3) | |
O2 | 0.58907 (14) | 0.17746 (9) | 0.50772 (13) | 0.0348 (4) | |
N1 | 0.31097 (14) | 0.44518 (8) | 0.45892 (11) | 0.0194 (3) | |
N2 | 0.49322 (14) | 0.34546 (8) | 0.55254 (12) | 0.0187 (3) | |
C8 | 0.1415 (2) | 0.61873 (11) | 0.59779 (17) | 0.0289 (4) | |
H8A | 0.183990 | 0.627682 | 0.662569 | 0.043* | |
H8B | 0.142254 | 0.663818 | 0.557848 | 0.043* | |
H8C | 0.059735 | 0.604933 | 0.606206 | 0.043* | |
C9 | 0.14895 (16) | 0.53872 (10) | 0.45433 (14) | 0.0204 (3) | |
C14 | 0.20650 (16) | 0.47886 (9) | 0.40699 (14) | 0.0197 (3) | |
C18 | 0.28817 (17) | 0.40155 (10) | 0.54900 (14) | 0.0212 (3) | |
H18A | 0.249331 | 0.354174 | 0.528992 | 0.025* | |
H18B | 0.234550 | 0.429674 | 0.588534 | 0.025* | |
C17 | 0.40524 (17) | 0.38590 (10) | 0.61203 (14) | 0.0206 (3) | |
H17A | 0.440209 | 0.433269 | 0.636801 | 0.025* | |
H17B | 0.389230 | 0.355387 | 0.669737 | 0.025* | |
C19 | 0.61458 (17) | 0.33932 (10) | 0.60931 (14) | 0.0216 (3) | |
H19A | 0.647514 | 0.389681 | 0.620168 | 0.026* | |
H19B | 0.667533 | 0.311805 | 0.568493 | 0.026* | |
C20 | 0.61356 (18) | 0.29977 (10) | 0.71096 (15) | 0.0243 (4) | |
H20 | 0.571147 | 0.332670 | 0.755111 | 0.029* | |
C21 | 0.74206 (19) | 0.29034 (11) | 0.75826 (15) | 0.0268 (4) | |
H21A | 0.783545 | 0.338567 | 0.761639 | 0.032* | |
H21B | 0.742433 | 0.270120 | 0.825894 | 0.032* | |
C22 | 0.92188 (18) | 0.23356 (10) | 0.70433 (15) | 0.0232 (4) | |
C31 | 0.96907 (17) | 0.18948 (10) | 0.62703 (14) | 0.0213 (3) | |
C30 | 0.89273 (17) | 0.14852 (10) | 0.55538 (14) | 0.0224 (4) | |
H30 | 0.809597 | 0.152666 | 0.555305 | 0.027* | |
C29 | 0.94107 (18) | 0.10269 (11) | 0.48598 (14) | 0.0241 (4) | |
H29 | 0.890608 | 0.074581 | 0.440851 | 0.029* | |
C28 | 1.06726 (18) | 0.09831 (12) | 0.48324 (15) | 0.0271 (4) | |
H28 | 1.099517 | 0.067484 | 0.436033 | 0.033* | |
C26 | 1.09601 (17) | 0.18491 (10) | 0.62498 (15) | 0.0233 (4) | |
C25 | 1.17235 (19) | 0.22240 (11) | 0.70157 (17) | 0.0289 (4) | |
H25 | 1.255420 | 0.221917 | 0.699174 | 0.035* | |
C24 | 1.1230 (2) | 0.25883 (11) | 0.77807 (17) | 0.0311 (4) | |
H24 | 1.173588 | 0.279856 | 0.830004 | 0.037* | |
C23 | 0.9969 (2) | 0.26539 (11) | 0.78030 (16) | 0.0280 (4) | |
H23 | 0.964970 | 0.290995 | 0.832672 | 0.034* | |
C15 | 0.38452 (17) | 0.39945 (11) | 0.39680 (14) | 0.0228 (4) | |
H15A | 0.395273 | 0.425774 | 0.334457 | 0.027* | |
H15B | 0.344476 | 0.351818 | 0.380298 | 0.027* | |
C16 | 0.50601 (17) | 0.38496 (10) | 0.45417 (14) | 0.0220 (4) | |
H16A | 0.554571 | 0.354167 | 0.413323 | 0.026* | |
H16B | 0.547342 | 0.432663 | 0.467109 | 0.026* | |
C13 | 0.16233 (18) | 0.45804 (10) | 0.30990 (15) | 0.0244 (4) | |
H13 | 0.199609 | 0.418929 | 0.278032 | 0.029* | |
C12 | 0.06336 (19) | 0.49440 (11) | 0.25906 (16) | 0.0269 (4) | |
H12 | 0.035438 | 0.479787 | 0.194111 | 0.032* | |
C11 | 0.00755 (18) | 0.55232 (11) | 0.30648 (16) | 0.0262 (4) | |
H11 | −0.058700 | 0.576568 | 0.273437 | 0.031* | |
C10 | 0.05003 (17) | 0.57463 (10) | 0.40366 (16) | 0.0244 (4) | |
H10 | 0.012014 | 0.613771 | 0.434842 | 0.029* | |
C27 | 1.14268 (18) | 0.13945 (12) | 0.55007 (16) | 0.0276 (4) | |
H27 | 1.225422 | 0.137387 | 0.546042 | 0.033* | |
C2 | 0.45753 (18) | 0.09659 (10) | 0.40672 (14) | 0.0220 (4) | |
C1 | 0.48327 (18) | 0.16839 (11) | 0.46559 (15) | 0.0255 (4) | |
C6 | 0.3158 (2) | 0.01201 (12) | 0.31287 (16) | 0.0289 (4) | |
H6 | 0.238226 | 0.001877 | 0.284420 | 0.035* | 0.23 |
C7 | 0.34187 (19) | 0.07966 (11) | 0.36356 (15) | 0.0258 (4) | |
H7A | 0.280449 | 0.114579 | 0.368817 | 0.031* | |
H7 | 0.570 (3) | 0.2115 (17) | 0.646 (2) | 0.043 (8)* | |
H2 | 0.465 (3) | 0.2926 (18) | 0.533 (2) | 0.050 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C3A | 0.0348 (10) | 0.0297 (9) | 0.0276 (9) | 0.0023 (7) | 0.0077 (7) | −0.0013 (7) |
C4A | 0.0387 (11) | 0.0217 (8) | 0.0230 (9) | 0.0086 (8) | 0.0077 (8) | 0.0006 (7) |
C5A | 0.0425 (12) | 0.0187 (8) | 0.0222 (9) | −0.0009 (8) | 0.0069 (8) | −0.0014 (7) |
O3 | 0.0199 (9) | 0.0397 (11) | 0.0395 (11) | 0.0015 (8) | −0.0012 (8) | −0.0163 (9) |
O4 | 0.038 (2) | 0.032 (2) | 0.036 (2) | 0.0099 (19) | −0.0002 (19) | −0.0096 (18) |
O5 | 0.059 (5) | 0.039 (4) | 0.046 (5) | −0.001 (4) | 0.000 (4) | −0.014 (3) |
C3B | 0.0348 (10) | 0.0297 (9) | 0.0276 (9) | 0.0023 (7) | 0.0077 (7) | −0.0013 (7) |
C4B | 0.0387 (11) | 0.0217 (8) | 0.0230 (9) | 0.0086 (8) | 0.0077 (8) | 0.0006 (7) |
C5B | 0.0425 (12) | 0.0187 (8) | 0.0222 (9) | −0.0009 (8) | 0.0069 (8) | −0.0014 (7) |
O6 | 0.0264 (7) | 0.0194 (6) | 0.0264 (7) | 0.0029 (5) | 0.0058 (5) | −0.0060 (5) |
O8 | 0.0257 (7) | 0.0244 (6) | 0.0316 (8) | 0.0053 (5) | 0.0015 (6) | −0.0089 (6) |
O7 | 0.0365 (8) | 0.0197 (6) | 0.0387 (9) | 0.0007 (6) | 0.0132 (7) | 0.0042 (6) |
O1 | 0.0323 (8) | 0.0181 (6) | 0.0414 (8) | −0.0002 (5) | 0.0106 (6) | −0.0061 (6) |
O2 | 0.0309 (8) | 0.0297 (7) | 0.0445 (9) | −0.0030 (6) | 0.0072 (7) | −0.0131 (7) |
N1 | 0.0217 (7) | 0.0172 (6) | 0.0201 (7) | 0.0022 (5) | 0.0072 (6) | −0.0001 (5) |
N2 | 0.0218 (7) | 0.0134 (6) | 0.0218 (7) | 0.0005 (5) | 0.0074 (6) | 0.0001 (5) |
C8 | 0.0344 (11) | 0.0210 (8) | 0.0328 (10) | 0.0038 (7) | 0.0106 (8) | −0.0070 (7) |
C9 | 0.0212 (8) | 0.0157 (7) | 0.0253 (9) | −0.0028 (6) | 0.0073 (7) | −0.0005 (6) |
C14 | 0.0215 (8) | 0.0153 (7) | 0.0229 (8) | −0.0010 (6) | 0.0057 (6) | 0.0005 (6) |
C18 | 0.0229 (8) | 0.0183 (7) | 0.0239 (9) | 0.0010 (6) | 0.0093 (7) | 0.0018 (6) |
C17 | 0.0242 (9) | 0.0176 (7) | 0.0212 (8) | 0.0040 (6) | 0.0096 (7) | 0.0003 (6) |
C19 | 0.0223 (8) | 0.0164 (7) | 0.0266 (9) | 0.0003 (6) | 0.0054 (7) | 0.0004 (6) |
C20 | 0.0302 (10) | 0.0183 (8) | 0.0254 (9) | 0.0049 (7) | 0.0081 (7) | 0.0003 (7) |
C21 | 0.0351 (10) | 0.0208 (8) | 0.0245 (9) | 0.0072 (7) | 0.0033 (8) | −0.0035 (7) |
C22 | 0.0271 (9) | 0.0155 (7) | 0.0268 (9) | 0.0010 (6) | 0.0015 (7) | 0.0021 (6) |
C31 | 0.0256 (9) | 0.0160 (7) | 0.0224 (8) | 0.0012 (6) | 0.0027 (7) | 0.0040 (6) |
C30 | 0.0219 (8) | 0.0219 (8) | 0.0235 (9) | 0.0022 (7) | 0.0027 (7) | 0.0015 (7) |
C29 | 0.0238 (9) | 0.0269 (9) | 0.0218 (9) | 0.0007 (7) | 0.0027 (7) | −0.0002 (7) |
C28 | 0.0264 (9) | 0.0319 (10) | 0.0240 (9) | 0.0005 (8) | 0.0080 (7) | −0.0003 (7) |
C26 | 0.0243 (9) | 0.0198 (8) | 0.0260 (9) | −0.0024 (7) | 0.0026 (7) | 0.0067 (7) |
C25 | 0.0257 (10) | 0.0229 (9) | 0.0372 (11) | −0.0050 (7) | −0.0015 (8) | 0.0042 (8) |
C24 | 0.0358 (11) | 0.0186 (8) | 0.0370 (11) | −0.0058 (8) | −0.0061 (9) | −0.0030 (8) |
C23 | 0.0366 (11) | 0.0164 (8) | 0.0301 (10) | 0.0004 (7) | −0.0014 (8) | −0.0028 (7) |
C15 | 0.0266 (9) | 0.0219 (8) | 0.0212 (8) | 0.0034 (7) | 0.0090 (7) | −0.0011 (6) |
C16 | 0.0256 (9) | 0.0192 (8) | 0.0229 (9) | 0.0015 (6) | 0.0114 (7) | 0.0018 (6) |
C13 | 0.0293 (10) | 0.0197 (8) | 0.0247 (9) | −0.0003 (7) | 0.0053 (7) | −0.0010 (7) |
C12 | 0.0295 (10) | 0.0248 (9) | 0.0261 (9) | −0.0021 (7) | 0.0005 (7) | 0.0024 (7) |
C11 | 0.0234 (9) | 0.0222 (8) | 0.0327 (10) | 0.0000 (7) | 0.0006 (7) | 0.0057 (7) |
C10 | 0.0231 (9) | 0.0168 (8) | 0.0341 (10) | 0.0008 (6) | 0.0073 (7) | 0.0011 (7) |
C27 | 0.0215 (9) | 0.0315 (10) | 0.0306 (10) | −0.0019 (7) | 0.0072 (7) | 0.0043 (8) |
C2 | 0.0294 (9) | 0.0165 (7) | 0.0215 (8) | −0.0008 (7) | 0.0093 (7) | 0.0000 (6) |
C1 | 0.0302 (10) | 0.0190 (8) | 0.0292 (10) | −0.0040 (7) | 0.0129 (8) | −0.0021 (7) |
C6 | 0.0346 (11) | 0.0263 (9) | 0.0266 (10) | −0.0021 (8) | 0.0073 (8) | −0.0019 (7) |
C7 | 0.0313 (10) | 0.0213 (8) | 0.0261 (9) | 0.0018 (7) | 0.0092 (8) | −0.0004 (7) |
C3A—O3 | 1.306 (3) | C19—C20 | 1.527 (3) |
C3A—C2 | 1.397 (3) | C19—H19A | 0.9700 |
C3A—C4A | 1.408 (3) | C19—H19B | 0.9700 |
C4A—O4 | 1.313 (5) | C20—C21 | 1.521 (3) |
C4A—C5A | 1.377 (3) | C20—H20 | 0.9800 |
C5A—O5 | 1.357 (8) | C21—H21A | 0.9700 |
C5A—C6 | 1.390 (3) | C21—H21B | 0.9700 |
O3—H3 | 0.8200 | C22—C23 | 1.374 (3) |
O4—H4 | 0.8200 | C22—C31 | 1.431 (3) |
O5—H5 | 0.8200 | C31—C30 | 1.420 (3) |
C3B—C2 | 1.397 (3) | C31—C26 | 1.421 (3) |
C3B—C4B | 1.408 (3) | C30—C29 | 1.377 (3) |
C3B—H3B | 0.9300 | C30—H30 | 0.9300 |
C4B—C5B | 1.377 (3) | C29—C28 | 1.413 (3) |
C4B—H4B | 0.9300 | C29—H29 | 0.9300 |
C5B—C6 | 1.390 (3) | C28—C27 | 1.377 (3) |
C5B—H5B | 0.9300 | C28—H28 | 0.9300 |
O6—C9 | 1.367 (2) | C26—C27 | 1.418 (3) |
O6—C8 | 1.435 (2) | C26—C25 | 1.432 (3) |
O8—C22 | 1.363 (2) | C25—C24 | 1.364 (3) |
O8—C21 | 1.433 (2) | C25—H25 | 0.9300 |
O7—C20 | 1.418 (2) | C24—C23 | 1.415 (3) |
O7—H7 | 0.86 (3) | C24—H24 | 0.9300 |
O1—C1 | 1.253 (2) | C23—H23 | 0.9300 |
O2—C1 | 1.270 (3) | C15—C16 | 1.516 (3) |
N1—C14 | 1.430 (2) | C15—H15A | 0.9700 |
N1—C15 | 1.462 (2) | C15—H15B | 0.9700 |
N1—C18 | 1.470 (2) | C16—H16A | 0.9700 |
N2—C19 | 1.493 (2) | C16—H16B | 0.9700 |
N2—C17 | 1.499 (2) | C13—C12 | 1.399 (3) |
N2—C16 | 1.505 (2) | C13—H13 | 0.9300 |
N2—H2 | 1.01 (3) | C12—C11 | 1.382 (3) |
C8—H8A | 0.9600 | C12—H12 | 0.9300 |
C8—H8B | 0.9600 | C11—C10 | 1.396 (3) |
C8—H8C | 0.9600 | C11—H11 | 0.9300 |
C9—C10 | 1.393 (3) | C10—H10 | 0.9300 |
C9—C14 | 1.417 (2) | C27—H27 | 0.9300 |
C14—C13 | 1.392 (3) | C2—C7 | 1.396 (3) |
C18—C17 | 1.513 (3) | C2—C1 | 1.508 (3) |
C18—H18A | 0.9700 | C6—C7 | 1.393 (3) |
C18—H18B | 0.9700 | C6—H6 | 0.9300 |
C17—H17A | 0.9700 | C7—H7A | 0.9300 |
C17—H17B | 0.9700 | ||
O3—C3A—C2 | 123.18 (19) | O8—C21—H21B | 110.5 |
O3—C3A—C4A | 116.98 (19) | C20—C21—H21B | 110.5 |
C2—C3A—C4A | 119.84 (19) | H21A—C21—H21B | 108.7 |
O4—C4A—C5A | 123.2 (3) | O8—C22—C23 | 125.24 (18) |
O4—C4A—C3A | 116.3 (3) | O8—C22—C31 | 113.71 (17) |
C5A—C4A—C3A | 120.43 (18) | C23—C22—C31 | 121.05 (19) |
O5—C5A—C4A | 130.8 (4) | C30—C31—C26 | 119.70 (17) |
O5—C5A—C6 | 108.4 (4) | C30—C31—C22 | 121.74 (17) |
C4A—C5A—C6 | 120.59 (18) | C26—C31—C22 | 118.52 (17) |
C3A—O3—H3 | 109.5 | C29—C30—C31 | 120.38 (18) |
C4A—O4—H4 | 109.5 | C29—C30—H30 | 119.8 |
C5A—O5—H5 | 109.5 | C31—C30—H30 | 119.8 |
C2—C3B—C4B | 119.84 (19) | C30—C29—C28 | 120.10 (18) |
C2—C3B—H3B | 120.1 | C30—C29—H29 | 119.9 |
C4B—C3B—H3B | 120.1 | C28—C29—H29 | 119.9 |
C5B—C4B—C3B | 120.43 (18) | C27—C28—C29 | 120.35 (19) |
C5B—C4B—H4B | 119.8 | C27—C28—H28 | 119.8 |
C3B—C4B—H4B | 119.8 | C29—C28—H28 | 119.8 |
C4B—C5B—C6 | 120.59 (18) | C27—C26—C31 | 118.43 (18) |
C4B—C5B—H5B | 119.7 | C27—C26—C25 | 122.21 (19) |
C6—C5B—H5B | 119.7 | C31—C26—C25 | 119.25 (18) |
C9—O6—C8 | 116.84 (15) | C24—C25—C26 | 119.90 (19) |
C22—O8—C21 | 119.12 (15) | C24—C25—H25 | 120.0 |
C20—O7—H7 | 104 (2) | C26—C25—H25 | 120.0 |
C14—N1—C15 | 115.51 (15) | C25—C24—C23 | 121.60 (19) |
C14—N1—C18 | 114.89 (14) | C25—C24—H24 | 119.2 |
C15—N1—C18 | 108.66 (14) | C23—C24—H24 | 119.2 |
C19—N2—C17 | 111.92 (14) | C22—C23—C24 | 119.4 (2) |
C19—N2—C16 | 108.79 (14) | C22—C23—H23 | 120.3 |
C17—N2—C16 | 110.99 (13) | C24—C23—H23 | 120.3 |
C19—N2—H2 | 108.0 (17) | N1—C15—C16 | 109.24 (15) |
C17—N2—H2 | 112.0 (18) | N1—C15—H15A | 109.8 |
C16—N2—H2 | 104.9 (18) | C16—C15—H15A | 109.8 |
O6—C8—H8A | 109.5 | N1—C15—H15B | 109.8 |
O6—C8—H8B | 109.5 | C16—C15—H15B | 109.8 |
H8A—C8—H8B | 109.5 | H15A—C15—H15B | 108.3 |
O6—C8—H8C | 109.5 | N2—C16—C15 | 111.54 (15) |
H8A—C8—H8C | 109.5 | N2—C16—H16A | 109.3 |
H8B—C8—H8C | 109.5 | C15—C16—H16A | 109.3 |
O6—C9—C10 | 124.36 (16) | N2—C16—H16B | 109.3 |
O6—C9—C14 | 115.89 (16) | C15—C16—H16B | 109.3 |
C10—C9—C14 | 119.72 (18) | H16A—C16—H16B | 108.0 |
C13—C14—C9 | 118.44 (17) | C14—C13—C12 | 121.71 (18) |
C13—C14—N1 | 122.92 (16) | C14—C13—H13 | 119.1 |
C9—C14—N1 | 118.56 (16) | C12—C13—H13 | 119.1 |
N1—C18—C17 | 110.21 (15) | C11—C12—C13 | 119.22 (19) |
N1—C18—H18A | 109.6 | C11—C12—H12 | 120.4 |
C17—C18—H18A | 109.6 | C13—C12—H12 | 120.4 |
N1—C18—H18B | 109.6 | C12—C11—C10 | 120.38 (18) |
C17—C18—H18B | 109.6 | C12—C11—H11 | 119.8 |
H18A—C18—H18B | 108.1 | C10—C11—H11 | 119.8 |
N2—C17—C18 | 111.53 (15) | C9—C10—C11 | 120.53 (18) |
N2—C17—H17A | 109.3 | C9—C10—H10 | 119.7 |
C18—C17—H17A | 109.3 | C11—C10—H10 | 119.7 |
N2—C17—H17B | 109.3 | C28—C27—C26 | 120.95 (18) |
C18—C17—H17B | 109.3 | C28—C27—H27 | 119.5 |
H17A—C17—H17B | 108.0 | C26—C27—H27 | 119.5 |
N2—C19—C20 | 113.81 (15) | C7—C2—C3A | 118.42 (17) |
N2—C19—H19A | 108.8 | C7—C2—C3B | 118.42 (17) |
C20—C19—H19A | 108.8 | C7—C2—C1 | 121.36 (17) |
N2—C19—H19B | 108.8 | C3A—C2—C1 | 120.16 (18) |
C20—C19—H19B | 108.8 | C3B—C2—C1 | 120.16 (18) |
H19A—C19—H19B | 107.7 | O1—C1—O2 | 123.45 (18) |
O7—C20—C21 | 112.55 (15) | O1—C1—C2 | 119.03 (18) |
O7—C20—C19 | 111.38 (16) | O2—C1—C2 | 117.51 (17) |
C21—C20—C19 | 109.60 (16) | C5B—C6—C7 | 118.8 (2) |
O7—C20—H20 | 107.7 | C5A—C6—C7 | 118.8 (2) |
C21—C20—H20 | 107.7 | C5A—C6—H6 | 120.6 |
C19—C20—H20 | 107.7 | C7—C6—H6 | 120.6 |
O8—C21—C20 | 106.22 (15) | C6—C7—C2 | 121.91 (19) |
O8—C21—H21A | 110.5 | C6—C7—H7A | 119.0 |
C20—C21—H21A | 110.5 | C2—C7—H7A | 119.0 |
O3—C3A—C4A—O4 | 3.8 (4) | C30—C31—C26—C25 | −175.91 (17) |
C2—C3A—C4A—O4 | −176.9 (3) | C22—C31—C26—C25 | 1.9 (3) |
O3—C3A—C4A—C5A | −179.1 (2) | C27—C26—C25—C24 | −173.03 (19) |
C2—C3A—C4A—C5A | 0.2 (3) | C31—C26—C25—C24 | 3.2 (3) |
O4—C4A—C5A—O5 | −9.4 (7) | C26—C25—C24—C23 | −4.6 (3) |
C3A—C4A—C5A—O5 | 173.7 (5) | O8—C22—C23—C24 | −176.62 (18) |
O4—C4A—C5A—C6 | 177.0 (3) | C31—C22—C23—C24 | 4.4 (3) |
C3A—C4A—C5A—C6 | 0.1 (3) | C25—C24—C23—C22 | 0.8 (3) |
C2—C3B—C4B—C5B | 0.2 (3) | C14—N1—C15—C16 | 165.31 (15) |
C3B—C4B—C5B—C6 | 0.1 (3) | C18—N1—C15—C16 | −63.90 (18) |
C8—O6—C9—C10 | 2.4 (3) | C19—N2—C16—C15 | −174.83 (14) |
C8—O6—C9—C14 | −179.54 (16) | C17—N2—C16—C15 | −51.26 (19) |
O6—C9—C14—C13 | −177.68 (16) | N1—C15—C16—N2 | 58.38 (19) |
C10—C9—C14—C13 | 0.5 (3) | C9—C14—C13—C12 | −0.2 (3) |
O6—C9—C14—N1 | −0.8 (2) | N1—C14—C13—C12 | −176.90 (17) |
C10—C9—C14—N1 | 177.33 (16) | C14—C13—C12—C11 | −0.3 (3) |
C15—N1—C14—C13 | 13.0 (2) | C13—C12—C11—C10 | 0.5 (3) |
C18—N1—C14—C13 | −114.79 (19) | O6—C9—C10—C11 | 177.72 (17) |
C15—N1—C14—C9 | −163.72 (16) | C14—C9—C10—C11 | −0.3 (3) |
C18—N1—C14—C9 | 68.5 (2) | C12—C11—C10—C9 | −0.2 (3) |
C14—N1—C18—C17 | −165.43 (14) | C29—C28—C27—C26 | 2.1 (3) |
C15—N1—C18—C17 | 63.44 (19) | C31—C26—C27—C28 | −2.5 (3) |
C19—N2—C17—C18 | 172.01 (14) | C25—C26—C27—C28 | 173.75 (19) |
C16—N2—C17—C18 | 50.25 (19) | O3—C3A—C2—C7 | 178.9 (2) |
N1—C18—C17—N2 | −56.73 (19) | C4A—C3A—C2—C7 | −0.3 (3) |
C17—N2—C19—C20 | 57.19 (19) | O3—C3A—C2—C1 | −3.9 (3) |
C16—N2—C19—C20 | −179.80 (14) | C4A—C3A—C2—C1 | 176.89 (18) |
N2—C19—C20—O7 | 49.9 (2) | C4B—C3B—C2—C7 | −0.3 (3) |
N2—C19—C20—C21 | 175.08 (14) | C4B—C3B—C2—C1 | 176.89 (18) |
C22—O8—C21—C20 | 164.40 (16) | C7—C2—C1—O1 | −3.4 (3) |
O7—C20—C21—O8 | 58.4 (2) | C3A—C2—C1—O1 | 179.48 (18) |
C19—C20—C21—O8 | −66.11 (19) | C3B—C2—C1—O1 | 179.48 (18) |
C21—O8—C22—C23 | 10.2 (3) | C7—C2—C1—O2 | 175.74 (18) |
C21—O8—C22—C31 | −170.82 (16) | C3A—C2—C1—O2 | −1.4 (3) |
O8—C22—C31—C30 | −7.0 (2) | C3B—C2—C1—O2 | −1.4 (3) |
C23—C22—C31—C30 | 172.03 (18) | C4B—C5B—C6—C7 | −0.3 (3) |
O8—C22—C31—C26 | 175.23 (16) | O5—C5A—C6—C7 | −175.2 (4) |
C23—C22—C31—C26 | −5.7 (3) | C4A—C5A—C6—C7 | −0.3 (3) |
C26—C31—C30—C29 | 2.0 (3) | C5B—C6—C7—C2 | 0.2 (3) |
C22—C31—C30—C29 | −175.74 (17) | C5A—C6—C7—C2 | 0.2 (3) |
C31—C30—C29—C28 | −2.4 (3) | C3A—C2—C7—C6 | 0.1 (3) |
C30—C29—C28—C27 | 0.3 (3) | C3B—C2—C7—C6 | 0.1 (3) |
C30—C31—C26—C27 | 0.4 (3) | C1—C2—C7—C6 | −177.07 (18) |
C22—C31—C26—C27 | 178.21 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O7i | 0.82 | 2.01 | 2.592 (9) | 127 |
C8—H8A···O5ii | 0.96 | 2.27 | 3.058 (9) | 139 |
C18—H18B···O6 | 0.97 | 2.37 | 2.953 (2) | 118 |
C19—H19B···O2 | 0.97 | 2.64 | 3.171 (2) | 115 |
C15—H15A···O4iii | 0.97 | 2.41 | 3.283 (5) | 150 |
C16—H16A···O5iii | 0.97 | 2.54 | 3.174 (9) | 123 |
O3—H3···O2 | 0.82 | 1.81 | 2.542 (3) | 147 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+1/2. |
C31H34N2O6.69 | F(000) = 1150 |
Mr = 541.64 | Dx = 1.358 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.404 (5) Å | Cell parameters from 9815 reflections |
b = 17.591 (8) Å | θ = 2.5–30.4° |
c = 13.269 (6) Å | µ = 0.10 mm−1 |
β = 95.526 (15)° | T = 100 K |
V = 2650 (2) Å3 | Block, colourless |
Z = 4 | 0.2 × 0.15 × 0.15 mm |
Bruker APEX-II CCD diffractometer | 6291 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.064 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1446 before and 0.0653 after correction. The Ratio of minimum to maximum transmission is 0.8326. The λ/2 correction factor is Not present. | θmax = 30.5°, θmin = 2.3° |
Tmin = 0.621, Tmax = 0.746 | h = −16→16 |
86570 measured reflections | k = −25→25 |
8037 independent reflections | l = −16→18 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.084 | H-atom parameters constrained |
wR(F2) = 0.175 | w = 1/[σ2(Fo2) + (0.0149P)2 + 5.2044P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.011 |
8037 reflections | Δρmax = 0.40 e Å−3 |
375 parameters | Δρmin = −0.37 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C3A | 0.5514 (3) | 0.95779 (16) | 0.39692 (18) | 0.0439 (7) | 0.92 |
C4A | 0.5264 (3) | 1.02693 (15) | 0.34624 (19) | 0.0460 (7) | 0.39 |
C7A | 0.3484 (3) | 0.92412 (16) | 0.3639 (2) | 0.0487 (8) | 0.38 |
O3 | 0.6625 (2) | 0.94469 (14) | 0.43383 (18) | 0.0538 (6) | 0.92 |
H3 | 0.666953 | 0.902726 | 0.460843 | 0.081* | 0.92 |
O4 | 0.6076 (4) | 1.0725 (3) | 0.3444 (4) | 0.0406 (11) | 0.39 |
H4 | 0.668094 | 1.053972 | 0.372612 | 0.061* | 0.39 |
O5 | 0.2808 (6) | 0.8816 (4) | 0.3701 (7) | 0.081 (3) | 0.38 |
H7A | 0.307052 | 0.847238 | 0.407465 | 0.121* | 0.38 |
C3B | 0.5514 (3) | 0.95779 (16) | 0.39692 (18) | 0.0439 (7) | 0.08 |
H3B | 0.627904 | 0.946859 | 0.423649 | 0.053* | 0.08 |
C4B | 0.5264 (3) | 1.02693 (15) | 0.34624 (19) | 0.0460 (7) | 0.61 |
H4B | 0.586514 | 1.062003 | 0.340799 | 0.055* | 0.61 |
C7B | 0.3484 (3) | 0.92412 (16) | 0.3639 (2) | 0.0487 (8) | 0.62 |
H7B | 0.287293 | 0.889880 | 0.369662 | 0.058* | 0.62 |
O6 | 0.20532 (16) | 0.43966 (10) | 0.55068 (12) | 0.0334 (4) | |
O8 | 0.79875 (19) | 0.75755 (11) | 0.69112 (15) | 0.0456 (5) | |
O7 | 0.5562 (2) | 0.76707 (10) | 0.70431 (14) | 0.0465 (5) | |
H7 | 0.571676 | 0.790469 | 0.653803 | 0.070* | |
O1 | 0.4030 (2) | 0.78781 (11) | 0.47387 (16) | 0.0474 (5) | |
O2 | 0.5898 (2) | 0.82281 (11) | 0.50682 (15) | 0.0476 (5) | |
N2 | 0.49231 (18) | 0.65427 (10) | 0.55209 (14) | 0.0268 (4) | |
H2 | 0.462797 | 0.706099 | 0.539785 | 0.032* | |
N1 | 0.31051 (17) | 0.55513 (11) | 0.46072 (14) | 0.0270 (4) | |
C9 | 0.1518 (2) | 0.46130 (13) | 0.45828 (17) | 0.0300 (5) | |
C16 | 0.4996 (2) | 0.61620 (12) | 0.45117 (16) | 0.0276 (4) | |
H16A | 0.544652 | 0.648013 | 0.409267 | 0.033* | |
H16B | 0.540698 | 0.568112 | 0.461398 | 0.033* | |
C14 | 0.2062 (2) | 0.52198 (13) | 0.41063 (17) | 0.0282 (4) | |
C13 | 0.1584 (2) | 0.54477 (14) | 0.31483 (18) | 0.0328 (5) | |
H13 | 0.193420 | 0.584507 | 0.282527 | 0.039* | |
C19 | 0.6135 (2) | 0.65913 (12) | 0.60585 (18) | 0.0305 (5) | |
H19A | 0.663369 | 0.687505 | 0.564095 | 0.037* | |
H19B | 0.645578 | 0.608213 | 0.614164 | 0.037* | |
C18 | 0.2917 (2) | 0.59802 (13) | 0.55289 (17) | 0.0310 (5) | |
H18A | 0.241250 | 0.569166 | 0.593628 | 0.037* | |
H18B | 0.252928 | 0.645830 | 0.534648 | 0.037* | |
C17 | 0.4088 (2) | 0.61322 (13) | 0.61342 (17) | 0.0299 (5) | |
H17A | 0.395781 | 0.643423 | 0.672488 | 0.036* | |
H17B | 0.443681 | 0.565307 | 0.636769 | 0.036* | |
C15 | 0.3792 (2) | 0.60228 (14) | 0.39732 (16) | 0.0299 (5) | |
H15A | 0.339375 | 0.650389 | 0.383300 | 0.036* | |
H15B | 0.386585 | 0.576863 | 0.333365 | 0.036* | |
C10 | 0.0526 (2) | 0.42674 (14) | 0.41004 (19) | 0.0351 (5) | |
H10 | 0.016744 | 0.387110 | 0.441853 | 0.042* | |
C31 | 0.9650 (3) | 0.80896 (14) | 0.6262 (2) | 0.0377 (6) | |
C11 | 0.0062 (2) | 0.45068 (16) | 0.3145 (2) | 0.0381 (5) | |
H11 | −0.060658 | 0.427183 | 0.282947 | 0.046* | |
C22 | 0.9187 (3) | 0.76328 (14) | 0.7011 (2) | 0.0435 (7) | |
C20 | 0.6172 (3) | 0.69698 (14) | 0.70946 (19) | 0.0392 (6) | |
H20 | 0.577079 | 0.663186 | 0.753744 | 0.047* | |
C2 | 0.4618 (3) | 0.90596 (14) | 0.40701 (18) | 0.0404 (6) | |
C8 | 0.1526 (3) | 0.37749 (15) | 0.5999 (2) | 0.0396 (6) | |
H8A | 0.149518 | 0.333645 | 0.556649 | 0.059* | |
H8B | 0.074248 | 0.391189 | 0.613605 | 0.059* | |
H8C | 0.198892 | 0.366054 | 0.662362 | 0.059* | |
C30 | 0.8918 (3) | 0.85087 (15) | 0.55445 (18) | 0.0374 (5) | |
H30 | 0.810394 | 0.846849 | 0.553449 | 0.045* | |
C1 | 0.4858 (3) | 0.83388 (15) | 0.46611 (19) | 0.0436 (7) | |
C12 | 0.0591 (2) | 0.50930 (15) | 0.26628 (19) | 0.0362 (5) | |
H12 | 0.028754 | 0.524958 | 0.202058 | 0.043* | |
C27 | 1.1356 (3) | 0.86034 (18) | 0.5523 (2) | 0.0483 (7) | |
H27 | 1.216669 | 0.862808 | 0.549704 | 0.058* | |
C6 | 0.3252 (3) | 0.99208 (16) | 0.3128 (2) | 0.0486 (7) | |
H6A | 0.249534 | 1.003039 | 0.283966 | 0.058* | 0.38 |
H6B | 0.249534 | 1.003039 | 0.283966 | 0.058* | 0.62 |
C26 | 1.0896 (3) | 0.81396 (15) | 0.6251 (2) | 0.0433 (7) | |
C5 | 0.4155 (3) | 1.04312 (15) | 0.30510 (18) | 0.0480 (8) | |
H5A | 0.400380 | 1.089004 | 0.271520 | 0.058* | 0.39 |
H5B | 0.400380 | 1.089004 | 0.271520 | 0.058* | 0.61 |
C21 | 0.7433 (3) | 0.70504 (15) | 0.7546 (2) | 0.0473 (7) | |
H21A | 0.746104 | 0.724329 | 0.823246 | 0.057* | |
H21B | 0.783006 | 0.656223 | 0.755916 | 0.057* | |
C28 | 1.0627 (3) | 0.90222 (19) | 0.4847 (2) | 0.0466 (7) | |
H28 | 1.094729 | 0.933653 | 0.438153 | 0.056* | |
C29 | 0.9394 (3) | 0.89745 (18) | 0.4862 (2) | 0.0440 (6) | |
H29 | 0.890300 | 0.925981 | 0.440730 | 0.053* | |
C23 | 0.9912 (3) | 0.73013 (16) | 0.7775 (3) | 0.0603 (10) | |
H23 | 0.959597 | 0.703426 | 0.829009 | 0.072* | |
C25 | 1.1629 (3) | 0.77496 (16) | 0.7020 (3) | 0.0585 (9) | |
H25 | 1.244262 | 0.775524 | 0.700775 | 0.070* | |
C24 | 1.1143 (4) | 0.73728 (18) | 0.7765 (3) | 0.0708 (12) | |
H24 | 1.163468 | 0.715464 | 0.828631 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C3A | 0.073 (2) | 0.0378 (14) | 0.0217 (11) | 0.0141 (13) | 0.0071 (11) | 0.0026 (10) |
C4A | 0.083 (2) | 0.0298 (12) | 0.0250 (11) | −0.0017 (13) | 0.0060 (13) | −0.0009 (10) |
C7A | 0.080 (2) | 0.0339 (14) | 0.0334 (13) | 0.0203 (15) | 0.0115 (14) | 0.0040 (11) |
O3 | 0.0673 (16) | 0.0510 (14) | 0.0428 (12) | 0.0050 (12) | 0.0048 (11) | 0.0189 (11) |
O4 | 0.043 (3) | 0.042 (3) | 0.034 (2) | −0.010 (2) | −0.006 (2) | 0.010 (2) |
O5 | 0.044 (3) | 0.070 (5) | 0.128 (7) | −0.020 (3) | 0.006 (4) | 0.059 (5) |
C3B | 0.073 (2) | 0.0378 (14) | 0.0217 (11) | 0.0141 (13) | 0.0071 (11) | 0.0026 (10) |
C4B | 0.083 (2) | 0.0298 (12) | 0.0250 (11) | −0.0017 (13) | 0.0060 (13) | −0.0009 (10) |
C7B | 0.080 (2) | 0.0339 (14) | 0.0334 (13) | 0.0203 (15) | 0.0115 (14) | 0.0040 (11) |
O6 | 0.0399 (10) | 0.0309 (8) | 0.0295 (8) | −0.0060 (7) | 0.0043 (7) | 0.0064 (7) |
O8 | 0.0598 (13) | 0.0334 (9) | 0.0409 (10) | −0.0150 (9) | −0.0092 (9) | 0.0079 (8) |
O7 | 0.0856 (16) | 0.0233 (8) | 0.0322 (9) | −0.0052 (9) | 0.0142 (10) | −0.0015 (7) |
O1 | 0.0669 (14) | 0.0284 (9) | 0.0489 (11) | 0.0123 (9) | 0.0161 (10) | 0.0103 (8) |
O2 | 0.0633 (14) | 0.0352 (10) | 0.0458 (11) | 0.0127 (9) | 0.0134 (10) | 0.0141 (8) |
N2 | 0.0394 (11) | 0.0161 (8) | 0.0255 (9) | −0.0015 (7) | 0.0066 (7) | 0.0003 (6) |
N1 | 0.0345 (10) | 0.0249 (9) | 0.0220 (8) | −0.0016 (7) | 0.0051 (7) | 0.0016 (7) |
C9 | 0.0338 (12) | 0.0281 (11) | 0.0285 (11) | 0.0016 (9) | 0.0054 (9) | 0.0002 (9) |
C16 | 0.0382 (12) | 0.0222 (10) | 0.0234 (10) | −0.0009 (9) | 0.0085 (8) | −0.0016 (8) |
C14 | 0.0310 (11) | 0.0270 (10) | 0.0273 (10) | 0.0004 (9) | 0.0066 (8) | 0.0000 (8) |
C13 | 0.0390 (13) | 0.0300 (11) | 0.0294 (11) | 0.0023 (10) | 0.0032 (9) | 0.0025 (9) |
C19 | 0.0417 (13) | 0.0176 (9) | 0.0318 (11) | −0.0041 (9) | 0.0012 (9) | 0.0008 (8) |
C18 | 0.0403 (13) | 0.0264 (10) | 0.0280 (11) | −0.0002 (9) | 0.0117 (9) | 0.0000 (8) |
C17 | 0.0458 (14) | 0.0213 (10) | 0.0240 (10) | −0.0043 (9) | 0.0095 (9) | 0.0000 (8) |
C15 | 0.0371 (12) | 0.0302 (11) | 0.0233 (10) | −0.0012 (9) | 0.0065 (9) | 0.0027 (8) |
C10 | 0.0367 (13) | 0.0322 (12) | 0.0368 (12) | −0.0034 (10) | 0.0061 (10) | −0.0011 (10) |
C31 | 0.0502 (15) | 0.0244 (11) | 0.0364 (13) | −0.0025 (10) | −0.0061 (11) | −0.0125 (9) |
C11 | 0.0358 (13) | 0.0390 (13) | 0.0390 (13) | −0.0002 (11) | 0.0004 (10) | −0.0054 (11) |
C22 | 0.0587 (18) | 0.0209 (11) | 0.0473 (15) | −0.0073 (11) | −0.0132 (13) | −0.0019 (10) |
C20 | 0.0655 (18) | 0.0220 (10) | 0.0299 (12) | −0.0114 (11) | 0.0037 (11) | 0.0030 (9) |
C2 | 0.076 (2) | 0.0234 (11) | 0.0247 (11) | 0.0158 (12) | 0.0170 (11) | 0.0033 (9) |
C8 | 0.0524 (16) | 0.0335 (13) | 0.0336 (12) | −0.0097 (11) | 0.0081 (11) | 0.0069 (10) |
C30 | 0.0442 (14) | 0.0392 (13) | 0.0279 (11) | −0.0054 (11) | −0.0006 (10) | −0.0046 (10) |
C1 | 0.076 (2) | 0.0289 (12) | 0.0289 (12) | 0.0226 (13) | 0.0173 (12) | 0.0047 (10) |
C12 | 0.0389 (13) | 0.0377 (13) | 0.0311 (12) | 0.0040 (11) | −0.0016 (10) | −0.0019 (10) |
C27 | 0.0455 (16) | 0.0531 (17) | 0.0459 (16) | −0.0004 (13) | 0.0023 (12) | −0.0216 (14) |
C6 | 0.079 (2) | 0.0334 (14) | 0.0333 (13) | 0.0168 (14) | 0.0062 (13) | 0.0044 (11) |
C26 | 0.0496 (16) | 0.0278 (12) | 0.0498 (16) | 0.0038 (11) | −0.0092 (12) | −0.0184 (11) |
C5 | 0.095 (2) | 0.0269 (12) | 0.0213 (11) | 0.0166 (14) | 0.0014 (13) | 0.0008 (9) |
C21 | 0.076 (2) | 0.0274 (12) | 0.0352 (13) | −0.0186 (13) | −0.0105 (13) | 0.0061 (10) |
C28 | 0.0465 (16) | 0.0621 (19) | 0.0316 (13) | −0.0044 (14) | 0.0056 (11) | −0.0077 (12) |
C29 | 0.0453 (16) | 0.0580 (17) | 0.0284 (12) | −0.0042 (13) | 0.0014 (11) | −0.0008 (12) |
C23 | 0.081 (2) | 0.0254 (13) | 0.069 (2) | −0.0089 (14) | −0.0205 (18) | 0.0121 (13) |
C25 | 0.057 (2) | 0.0278 (13) | 0.086 (2) | 0.0060 (13) | −0.0173 (17) | −0.0087 (15) |
C24 | 0.075 (2) | 0.0279 (14) | 0.102 (3) | 0.0054 (15) | −0.032 (2) | 0.0110 (17) |
C3A—O3 | 1.334 (4) | C19—H19B | 0.9700 |
C3A—C2 | 1.385 (4) | C18—C17 | 1.514 (4) |
C3A—C4A | 1.406 (4) | C18—H18A | 0.9700 |
C4A—O4 | 1.227 (5) | C18—H18B | 0.9700 |
C4A—C5 | 1.359 (5) | C17—H17A | 0.9700 |
C7A—O5 | 1.083 (6) | C17—H17B | 0.9700 |
C7A—C6 | 1.387 (4) | C15—H15A | 0.9700 |
C7A—C2 | 1.400 (5) | C15—H15B | 0.9700 |
O3—H3 | 0.8200 | C10—C11 | 1.392 (4) |
O4—H4 | 0.8200 | C10—H10 | 0.9300 |
O5—H7A | 0.8200 | C31—C30 | 1.412 (4) |
C3B—C2 | 1.385 (4) | C31—C22 | 1.418 (4) |
C3B—C4B | 1.406 (4) | C31—C26 | 1.426 (4) |
C3B—H3B | 0.9300 | C11—C12 | 1.382 (4) |
C4B—C5 | 1.359 (5) | C11—H11 | 0.9300 |
C4B—H4B | 0.9300 | C22—C23 | 1.375 (4) |
C7B—C6 | 1.387 (4) | C20—C21 | 1.510 (4) |
C7B—C2 | 1.400 (5) | C20—H20 | 0.9800 |
C7B—H7B | 0.9300 | C2—C1 | 1.502 (3) |
O6—C9 | 1.370 (3) | C8—H8A | 0.9600 |
O6—C8 | 1.435 (3) | C8—H8B | 0.9600 |
O8—C22 | 1.366 (4) | C8—H8C | 0.9600 |
O8—C21 | 1.437 (3) | C30—C29 | 1.372 (4) |
O7—C20 | 1.414 (3) | C30—H30 | 0.9300 |
O7—H7 | 0.8200 | C12—H12 | 0.9300 |
O1—C1 | 1.256 (4) | C27—C28 | 1.376 (4) |
O2—C1 | 1.270 (4) | C27—C26 | 1.403 (5) |
N2—C19 | 1.495 (3) | C27—H27 | 0.9300 |
N2—C17 | 1.497 (3) | C6—C5 | 1.377 (5) |
N2—C16 | 1.507 (3) | C6—H6A | 0.9300 |
N2—H2 | 0.9800 | C6—H6B | 0.9300 |
N1—C14 | 1.430 (3) | C26—C25 | 1.431 (4) |
N1—C15 | 1.462 (3) | C5—H5A | 0.9300 |
N1—C18 | 1.470 (3) | C5—H5B | 0.9300 |
C9—C10 | 1.385 (3) | C21—H21A | 0.9700 |
C9—C14 | 1.414 (3) | C21—H21B | 0.9700 |
C16—C15 | 1.506 (3) | C28—C29 | 1.410 (4) |
C16—H16A | 0.9700 | C28—H28 | 0.9300 |
C16—H16B | 0.9700 | C29—H29 | 0.9300 |
C14—C13 | 1.393 (3) | C23—C24 | 1.411 (5) |
C13—C12 | 1.395 (4) | C23—H23 | 0.9300 |
C13—H13 | 0.9300 | C25—C24 | 1.353 (6) |
C19—C20 | 1.524 (3) | C25—H25 | 0.9300 |
C19—H19A | 0.9700 | C24—H24 | 0.9300 |
O3—C3A—C2 | 122.3 (2) | C30—C31—C22 | 122.2 (3) |
O3—C3A—C4A | 117.8 (3) | C30—C31—C26 | 119.0 (3) |
C2—C3A—C4A | 119.9 (3) | C22—C31—C26 | 118.8 (3) |
O4—C4A—C5 | 122.0 (3) | C12—C11—C10 | 120.1 (2) |
O4—C4A—C3A | 117.2 (4) | C12—C11—H11 | 119.9 |
C5—C4A—C3A | 120.7 (3) | C10—C11—H11 | 119.9 |
O5—C7A—C6 | 121.9 (5) | O8—C22—C23 | 124.4 (3) |
O5—C7A—C2 | 116.6 (4) | O8—C22—C31 | 114.3 (2) |
C6—C7A—C2 | 121.4 (3) | C23—C22—C31 | 121.3 (3) |
C3A—O3—H3 | 109.5 | O7—C20—C21 | 112.5 (2) |
C4A—O4—H4 | 109.5 | O7—C20—C19 | 111.5 (2) |
C7A—O5—H7A | 109.5 | C21—C20—C19 | 110.0 (2) |
C2—C3B—C4B | 119.9 (3) | O7—C20—H20 | 107.5 |
C2—C3B—H3B | 120.0 | C21—C20—H20 | 107.5 |
C4B—C3B—H3B | 120.0 | C19—C20—H20 | 107.5 |
C5—C4B—C3B | 120.7 (3) | C3B—C2—C7B | 118.1 (2) |
C5—C4B—H4B | 119.6 | C3A—C2—C7A | 118.1 (2) |
C3B—C4B—H4B | 119.6 | C3B—C2—C1 | 120.5 (3) |
C6—C7B—C2 | 121.4 (3) | C3A—C2—C1 | 120.5 (3) |
C6—C7B—H7B | 119.3 | C7B—C2—C1 | 121.4 (3) |
C2—C7B—H7B | 119.3 | C7A—C2—C1 | 121.4 (3) |
C9—O6—C8 | 116.7 (2) | O6—C8—H8A | 109.5 |
C22—O8—C21 | 118.9 (2) | O6—C8—H8B | 109.5 |
C20—O7—H7 | 109.5 | H8A—C8—H8B | 109.5 |
C19—N2—C17 | 112.05 (18) | O6—C8—H8C | 109.5 |
C19—N2—C16 | 108.76 (18) | H8A—C8—H8C | 109.5 |
C17—N2—C16 | 111.19 (17) | H8B—C8—H8C | 109.5 |
C19—N2—H2 | 108.2 | C29—C30—C31 | 120.7 (3) |
C17—N2—H2 | 108.2 | C29—C30—H30 | 119.6 |
C16—N2—H2 | 108.2 | C31—C30—H30 | 119.6 |
C14—N1—C15 | 115.59 (18) | O1—C1—O2 | 123.0 (2) |
C14—N1—C18 | 114.49 (19) | O1—C1—C2 | 119.1 (3) |
C15—N1—C18 | 108.46 (18) | O2—C1—C2 | 117.9 (3) |
O6—C9—C10 | 124.4 (2) | C11—C12—C13 | 119.4 (2) |
O6—C9—C14 | 115.6 (2) | C11—C12—H12 | 120.3 |
C10—C9—C14 | 119.9 (2) | C13—C12—H12 | 120.3 |
C15—C16—N2 | 111.58 (18) | C28—C27—C26 | 121.2 (3) |
C15—C16—H16A | 109.3 | C28—C27—H27 | 119.4 |
N2—C16—H16A | 109.3 | C26—C27—H27 | 119.4 |
C15—C16—H16B | 109.3 | C5—C6—C7A | 119.3 (3) |
N2—C16—H16B | 109.3 | C5—C6—C7B | 119.3 (3) |
H16A—C16—H16B | 108.0 | C5—C6—H6A | 120.4 |
C13—C14—C9 | 118.4 (2) | C7A—C6—H6A | 120.4 |
C13—C14—N1 | 122.8 (2) | C5—C6—H6B | 120.4 |
C9—C14—N1 | 118.8 (2) | C7B—C6—H6B | 120.4 |
C14—C13—C12 | 121.5 (2) | C27—C26—C31 | 118.8 (3) |
C14—C13—H13 | 119.3 | C27—C26—C25 | 122.6 (3) |
C12—C13—H13 | 119.3 | C31—C26—C25 | 118.5 (3) |
N2—C19—C20 | 113.6 (2) | C4B—C5—C6 | 120.5 (3) |
N2—C19—H19A | 108.9 | C4A—C5—C6 | 120.5 (3) |
C20—C19—H19A | 108.9 | C4A—C5—H5A | 119.8 |
N2—C19—H19B | 108.9 | C6—C5—H5A | 119.8 |
C20—C19—H19B | 108.9 | C4B—C5—H5B | 119.8 |
H19A—C19—H19B | 107.7 | C6—C5—H5B | 119.8 |
N1—C18—C17 | 109.89 (19) | O8—C21—C20 | 106.5 (2) |
N1—C18—H18A | 109.7 | O8—C21—H21A | 110.4 |
C17—C18—H18A | 109.7 | C20—C21—H21A | 110.4 |
N1—C18—H18B | 109.7 | O8—C21—H21B | 110.4 |
C17—C18—H18B | 109.7 | C20—C21—H21B | 110.4 |
H18A—C18—H18B | 108.2 | H21A—C21—H21B | 108.6 |
N2—C17—C18 | 111.81 (18) | C27—C28—C29 | 120.0 (3) |
N2—C17—H17A | 109.3 | C27—C28—H28 | 120.0 |
C18—C17—H17A | 109.3 | C29—C28—H28 | 120.0 |
N2—C17—H17B | 109.3 | C30—C29—C28 | 120.2 (3) |
C18—C17—H17B | 109.3 | C30—C29—H29 | 119.9 |
H17A—C17—H17B | 107.9 | C28—C29—H29 | 119.9 |
N1—C15—C16 | 109.52 (18) | C22—C23—C24 | 118.9 (3) |
N1—C15—H15A | 109.8 | C22—C23—H23 | 120.5 |
C16—C15—H15A | 109.8 | C24—C23—H23 | 120.5 |
N1—C15—H15B | 109.8 | C24—C25—C26 | 120.3 (3) |
C16—C15—H15B | 109.8 | C24—C25—H25 | 119.8 |
H15A—C15—H15B | 108.2 | C26—C25—H25 | 119.8 |
C9—C10—C11 | 120.7 (2) | C25—C24—C23 | 121.9 (3) |
C9—C10—H10 | 119.6 | C25—C24—H24 | 119.1 |
C11—C10—H10 | 119.6 | C23—C24—H24 | 119.1 |
C62H67.80N4O12.63 | F(000) = 1138 |
Mr = 1071.08 | Dx = 1.351 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.237 (5) Å | Cell parameters from 9929 reflections |
b = 17.571 (6) Å | θ = 2.6–29.6° |
c = 13.374 (6) Å | µ = 0.10 mm−1 |
β = 94.584 (16)° | T = 100 K |
V = 2632.4 (18) Å3 | Block, colourless |
Z = 2 | 0.2 × 0.15 × 0.1 mm |
Bruker APEX-II CCD diffractometer | 11616 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.046 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0877 before and 0.0593 after correction. The Ratio of minimum to maximum transmission is 0.9383. The λ/2 correction factor is Not present. | θmax = 29.6°, θmin = 2.3° |
Tmin = 0.700, Tmax = 0.746 | h = −15→15 |
80672 measured reflections | k = −24→24 |
14648 independent reflections | l = −18→18 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.064P)2 + 1.2266P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.153 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.52 e Å−3 |
14648 reflections | Δρmin = −0.48 e Å−3 |
729 parameters | Absolute structure: Flack x determined using 4625 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
1 restraint | Absolute structure parameter: 0.4 (4) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C6A | 0.4485 (4) | 0.5398 (3) | 0.3526 (3) | 0.0345 (9) | 0.91 |
C4A | 0.5945 (4) | 0.4604 (3) | 0.4454 (3) | 0.0381 (9) | 0.4 |
H4A | 0.613979 | 0.415508 | 0.479807 | 0.046* | 0.4 |
C14A | 0.5520 (4) | 0.4604 (3) | 0.1440 (3) | 0.0381 (10) | 0.9 |
C10A | 0.3476 (4) | 0.4240 (3) | 0.1104 (4) | 0.0416 (10) | 0.42 |
O4 | 0.3356 (3) | 0.5470 (2) | 0.3130 (3) | 0.0481 (9) | 0.91 |
H4 | 0.328892 | 0.586704 | 0.280756 | 0.072* | 0.91 |
O5 | 0.6634 (3) | 0.4476 (3) | 0.1800 (3) | 0.0488 (10) | 0.9 |
H5 | 0.668736 | 0.404407 | 0.203284 | 0.073* | 0.9 |
O8 | 0.2824 (8) | 0.3741 (6) | 0.1080 (9) | 0.091 (3) | 0.42 |
H8 | 0.319515 | 0.334316 | 0.118336 | 0.136* | 0.42 |
C6B | 0.4485 (4) | 0.5398 (3) | 0.3526 (3) | 0.0345 (9) | 0.09 |
H6B | 0.370563 | 0.547526 | 0.325608 | 0.041* | 0.09 |
C4B | 0.5945 (4) | 0.4604 (3) | 0.4454 (3) | 0.0381 (9) | 0.6 |
C14B | 0.5520 (4) | 0.4604 (3) | 0.1440 (3) | 0.0381 (10) | 0.1 |
H14B | 0.629111 | 0.450734 | 0.171509 | 0.046* | 0.1 |
C10B | 0.3476 (4) | 0.4240 (3) | 0.1104 (4) | 0.0416 (10) | 0.58 |
H10B | 0.286118 | 0.389270 | 0.116682 | 0.050* | 0.58 |
O001 | 0.7934 (2) | 1.05904 (16) | 0.2009 (2) | 0.0301 (6) | |
O0AA | 0.1916 (2) | −0.05852 (17) | 0.2971 (2) | 0.0340 (6) | |
O6 | 0.5892 (3) | 0.3236 (2) | 0.2524 (3) | 0.0425 (8) | |
O1AA | 0.1961 (3) | 0.73932 (18) | 0.0567 (2) | 0.0399 (7) | |
O003 | 0.7918 (3) | 0.25715 (19) | 0.4373 (3) | 0.0433 (8) | |
O7 | 0.4017 (3) | 0.28757 (19) | 0.2172 (3) | 0.0445 (8) | |
O005 | 0.4422 (3) | 0.73040 (19) | 0.0489 (2) | 0.0432 (8) | |
H005 | 0.420175 | 0.706848 | 0.097045 | 0.065* | |
O2 | 0.5881 (3) | 0.71428 (19) | 0.2757 (3) | 0.0447 (8) | |
O1 | 0.4014 (3) | 0.6740 (2) | 0.2416 (3) | 0.0434 (8) | |
N00A | 0.3037 (3) | 0.05450 (19) | 0.2075 (2) | 0.0281 (7) | |
C00B | 0.8434 (3) | 1.0383 (2) | 0.2940 (3) | 0.0281 (8) | |
N00C | 0.6813 (3) | 0.94525 (19) | 0.2903 (2) | 0.0277 (6) | |
N00E | 0.4856 (3) | 0.15379 (19) | 0.2993 (3) | 0.0293 (7) | |
H00G | 0.456942 | 0.205655 | 0.285034 | 0.035* | |
N00L | 0.5003 (3) | 0.84509 (18) | 0.1983 (3) | 0.0270 (6) | |
H00L | 0.529633 | 0.793436 | 0.212892 | 0.032* | |
C00M | 0.4873 (3) | 0.8847 (2) | 0.2948 (3) | 0.0302 (8) | |
H00A | 0.438594 | 0.853984 | 0.335868 | 0.036* | |
H00B | 0.446591 | 0.932813 | 0.281751 | 0.036* | |
C00R | 0.6074 (4) | 0.8995 (2) | 0.3519 (3) | 0.0317 (8) | |
H00C | 0.595854 | 0.926041 | 0.413934 | 0.038* | |
H00D | 0.646815 | 0.851475 | 0.368444 | 0.038* | |
C00S | 0.3964 (4) | 0.1142 (2) | 0.3578 (3) | 0.0324 (8) | |
H00H | 0.381075 | 0.145002 | 0.415550 | 0.039* | |
H00I | 0.429619 | 0.066084 | 0.382243 | 0.039* | |
C00T | 0.3802 (4) | 0.8005 (3) | 0.0393 (3) | 0.0369 (9) | |
H00T | 0.422790 | 0.833359 | −0.005103 | 0.044* | |
C00U | 0.7040 (3) | 0.9009 (2) | 0.2009 (3) | 0.0298 (8) | |
H00E | 0.741896 | 0.853070 | 0.220998 | 0.036* | |
H00F | 0.757937 | 0.928805 | 0.161162 | 0.036* | |
C00V | 0.9131 (4) | 0.2631 (2) | 0.4504 (3) | 0.0357 (9) | |
C00W | 0.0271 (4) | 0.6880 (2) | 0.1235 (3) | 0.0331 (9) | |
C00Y | 0.1363 (4) | −0.1197 (3) | 0.3468 (4) | 0.0393 (10) | |
H00J | 0.140392 | −0.165336 | 0.307835 | 0.059* | |
H00K | 0.054233 | −0.107272 | 0.354131 | 0.059* | |
H00M | 0.177112 | −0.127423 | 0.411850 | 0.059* | |
C8 | 0.4845 (4) | 0.3338 (3) | 0.2107 (4) | 0.0368 (9) | |
C010 | 0.8516 (4) | 1.1198 (3) | 0.1521 (4) | 0.0373 (9) | |
H01A | 0.807686 | 1.131320 | 0.089367 | 0.056* | |
H01B | 0.931244 | 1.104594 | 0.140064 | 0.056* | |
H01C | 0.854690 | 1.164134 | 0.194165 | 0.056* | |
C011 | 0.9270 (4) | 0.9923 (3) | 0.4866 (3) | 0.0352 (9) | |
H011 | 0.954489 | 0.977215 | 0.551018 | 0.042* | |
C5 | 0.4792 (4) | 0.4715 (3) | 0.4036 (3) | 0.0381 (9) | |
H5A | 0.421826 | 0.433934 | 0.409220 | 0.046* | 0.91 |
H5B | 0.421826 | 0.433934 | 0.409220 | 0.046* | 0.09 |
C013 | 0.0532 (4) | 0.6014 (3) | 0.2638 (3) | 0.0368 (9) | |
H013 | 0.102742 | 0.574247 | 0.310052 | 0.044* | |
C014 | 0.2811 (3) | 0.0996 (2) | 0.2972 (3) | 0.0328 (8) | |
H01K | 0.227222 | 0.072045 | 0.337317 | 0.039* | |
H01L | 0.243870 | 0.147533 | 0.276963 | 0.039* | |
C015 | 1.0687 (4) | 0.4003 (3) | 0.2377 (4) | 0.0409 (10) | |
H015 | 1.102745 | 0.431667 | 0.191770 | 0.049* | |
C016 | 0.8927 (4) | 0.3484 (3) | 0.3027 (3) | 0.0337 (9) | |
H016 | 0.810041 | 0.343411 | 0.299261 | 0.040* | |
C017 | −0.1726 (4) | 0.7216 (3) | 0.0475 (4) | 0.0459 (11) | |
H017 | −0.255304 | 0.720798 | 0.048277 | 0.055* | |
C018 | 0.3781 (3) | 0.0999 (3) | 0.1447 (3) | 0.0306 (8) | |
H01M | 0.339325 | 0.148061 | 0.128181 | 0.037* | |
H01N | 0.388519 | 0.072989 | 0.082638 | 0.037* | |
C019 | 1.0908 (4) | 0.3129 (2) | 0.3786 (3) | 0.0356 (9) | |
C01A | −0.1218 (5) | 0.7585 (3) | −0.0258 (5) | 0.0533 (14) | |
H01D | −0.170760 | 0.780648 | −0.077166 | 0.064* | |
C01B | 0.7305 (4) | 0.2084 (3) | 0.5014 (3) | 0.0428 (10) | |
H01P | 0.730079 | 0.230461 | 0.567890 | 0.051* | |
H01Q | 0.769300 | 0.159098 | 0.507203 | 0.051* | |
C01C | 0.5883 (3) | 0.8853 (2) | 0.1383 (3) | 0.0291 (8) | |
H01E | 0.554151 | 0.933051 | 0.113422 | 0.035* | |
H01F | 0.604430 | 0.854277 | 0.080937 | 0.035* | |
O1D | 0.5446 (3) | 0.27112 (19) | 0.4430 (3) | 0.0464 (8) | |
H1D | 0.559193 | 0.290726 | 0.389686 | 0.070* | |
C01F | 0.0030 (5) | 0.7651 (3) | −0.0281 (4) | 0.0475 (12) | |
H01G | 0.035404 | 0.790718 | −0.080383 | 0.057* | |
C1F | 0.1562 (4) | 0.0416 (3) | 0.0602 (3) | 0.0350 (9) | |
H1F | 0.193291 | 0.080712 | 0.027664 | 0.042* | |
C01G | −0.1455 (4) | 0.6370 (3) | 0.1975 (3) | 0.0404 (10) | |
H01H | −0.227778 | 0.634244 | 0.200497 | 0.048* | |
C1G | 0.7851 (3) | 0.9786 (2) | 0.3414 (3) | 0.0271 (7) | |
C01H | 0.1422 (3) | −0.0387 (2) | 0.2050 (3) | 0.0289 (8) | |
C3 | 0.6808 (4) | 0.5153 (3) | 0.4366 (4) | 0.0413 (10) | |
H3A | 0.758482 | 0.507332 | 0.463979 | 0.050* | 0.4 |
H3B | 0.758482 | 0.507332 | 0.463979 | 0.050* | 0.6 |
C9 | 0.4611 (4) | 0.4067 (2) | 0.1530 (3) | 0.0330 (8) | |
C01J | 1.1405 (4) | 0.3599 (3) | 0.3054 (4) | 0.0425 (11) | |
H01R | 1.223000 | 0.362956 | 0.303878 | 0.051* | |
C1J | 0.9422 (3) | 1.0732 (2) | 0.3430 (3) | 0.0310 (8) | |
H1J | 0.980901 | 1.112240 | 0.311578 | 0.037* | |
C01K | 0.0579 (4) | 0.0051 (3) | 0.0107 (4) | 0.0384 (10) | |
H01S | 0.030557 | 0.019478 | −0.054092 | 0.046* | |
C11 | 0.3227 (5) | 0.4915 (3) | 0.0586 (4) | 0.0446 (11) | |
H11 | 0.246627 | 0.501417 | 0.028958 | 0.054* | 0.42 |
H11A | 0.246627 | 0.501417 | 0.028958 | 0.054* | 0.58 |
C01M | 0.4972 (3) | 0.1137 (2) | 0.2000 (3) | 0.0288 (8) | |
H01T | 0.545610 | 0.144555 | 0.158787 | 0.035* | |
H01U | 0.537679 | 0.065471 | 0.212280 | 0.035* | |
C01N | 0.2532 (4) | 0.7917 (3) | −0.0061 (3) | 0.0419 (10) | |
H01I | 0.212405 | 0.840359 | −0.008019 | 0.050* | |
H01J | 0.252424 | 0.772059 | −0.073935 | 0.050* | |
C1N | 0.0017 (4) | −0.0525 (3) | 0.0592 (4) | 0.0374 (9) | |
H1N | −0.064766 | −0.076462 | 0.027505 | 0.045* | |
C01O | 0.1019 (4) | 0.6474 (3) | 0.1943 (3) | 0.0349 (9) | |
H01O | 0.184343 | 0.651585 | 0.194046 | 0.042* | |
C01P | 0.9645 (4) | 0.3072 (2) | 0.3765 (3) | 0.0324 (8) | |
C7 | 0.5061 (4) | 0.6660 (3) | 0.2830 (3) | 0.0369 (9) | |
C01Q | 0.0441 (4) | −0.0746 (3) | 0.1551 (4) | 0.0354 (9) | |
H01X | 0.006385 | −0.114024 | 0.186607 | 0.042* | |
C1Q | 0.6063 (4) | 0.1588 (2) | 0.3537 (3) | 0.0308 (8) | |
H1QA | 0.659603 | 0.185468 | 0.312047 | 0.037* | |
H1QB | 0.637539 | 0.107873 | 0.365476 | 0.037* | |
C01R | 0.9439 (4) | 0.3952 (3) | 0.2366 (3) | 0.0386 (10) | |
H01Y | 0.895921 | 0.423676 | 0.190744 | 0.046* | |
C01S | −0.0987 (4) | 0.6827 (3) | 0.1255 (4) | 0.0396 (10) | |
C01T | 0.9835 (5) | 0.2302 (3) | 0.5281 (4) | 0.0475 (12) | |
H01Z | 0.948826 | 0.204015 | 0.578756 | 0.057* | |
C1 | 0.5341 (4) | 0.5955 (3) | 0.3426 (3) | 0.0342 (9) | |
C01V | −0.0715 (4) | 0.5955 (3) | 0.2649 (3) | 0.0402 (10) | |
H01V | −0.104367 | 0.563713 | 0.311013 | 0.048* | |
C01W | 0.8285 (4) | 0.9571 (2) | 0.4377 (3) | 0.0318 (8) | |
H01W | 0.790580 | 0.918165 | 0.469853 | 0.038* | |
C12 | 0.4134 (5) | 0.5430 (3) | 0.0525 (3) | 0.0428 (11) | |
H12 | 0.397473 | 0.588986 | 0.019639 | 0.051* | |
C2 | 0.6509 (4) | 0.5822 (3) | 0.3867 (3) | 0.0391 (10) | |
H2 | 0.708955 | 0.619509 | 0.381983 | 0.047* | |
C01Z | 0.2002 (3) | 0.0212 (2) | 0.1561 (3) | 0.0300 (8) | |
C020 | 0.0753 (4) | 0.7337 (2) | 0.0469 (4) | 0.0379 (9) | |
C021 | 1.1625 (4) | 0.2749 (3) | 0.4544 (4) | 0.0473 (12) | |
H021 | 1.245230 | 0.275456 | 0.453774 | 0.057* | |
C022 | 0.3806 (4) | 0.8396 (2) | 0.1408 (3) | 0.0324 (8) | |
H02A | 0.348907 | 0.890621 | 0.130599 | 0.039* | |
H02B | 0.326968 | 0.812190 | 0.181361 | 0.039* | |
C13 | 0.5252 (5) | 0.5290 (3) | 0.0928 (3) | 0.0435 (11) | |
H13 | 0.584949 | 0.564948 | 0.086709 | 0.052* | 0.9 |
H13A | 0.584949 | 0.564948 | 0.086709 | 0.052* | 0.1 |
C024 | 0.6040 (4) | 0.2002 (2) | 0.4539 (3) | 0.0387 (10) | |
H024 | 0.559631 | 0.168442 | 0.498241 | 0.046* | |
C025 | 0.9838 (4) | 1.0498 (3) | 0.4392 (3) | 0.0354 (9) | |
H025 | 1.050406 | 1.073290 | 0.471514 | 0.043* | |
C026 | 1.1094 (5) | 0.2369 (3) | 0.5296 (4) | 0.0527 (13) | |
H026 | 1.157060 | 0.215336 | 0.582195 | 0.063* | |
O3 | 0.6389 (6) | 0.4018 (4) | 0.5012 (5) | 0.0422 (14) | 0.4 |
H3 | 0.612650 | 0.361710 | 0.477043 | 0.063* | 0.4 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C6A | 0.046 (2) | 0.033 (2) | 0.0247 (19) | 0.0023 (17) | 0.0085 (16) | 0.0044 (17) |
C4A | 0.055 (2) | 0.035 (2) | 0.025 (2) | 0.0066 (18) | 0.0063 (17) | 0.0002 (17) |
C14A | 0.058 (3) | 0.030 (2) | 0.028 (2) | −0.0013 (18) | 0.0125 (18) | 0.0023 (17) |
C10A | 0.053 (3) | 0.032 (2) | 0.041 (2) | 0.0113 (18) | 0.0119 (19) | −0.0014 (18) |
O4 | 0.0479 (18) | 0.047 (2) | 0.051 (2) | 0.0039 (16) | 0.0083 (15) | 0.0233 (18) |
O5 | 0.051 (2) | 0.051 (2) | 0.045 (2) | −0.0127 (17) | 0.0056 (16) | 0.0194 (18) |
O8 | 0.073 (6) | 0.085 (7) | 0.113 (8) | −0.042 (5) | −0.003 (6) | 0.056 (6) |
C6B | 0.046 (2) | 0.033 (2) | 0.0247 (19) | 0.0023 (17) | 0.0085 (16) | 0.0044 (17) |
C4B | 0.055 (2) | 0.035 (2) | 0.025 (2) | 0.0066 (18) | 0.0063 (17) | 0.0002 (17) |
C14B | 0.058 (3) | 0.030 (2) | 0.028 (2) | −0.0013 (18) | 0.0125 (18) | 0.0023 (17) |
C10B | 0.053 (3) | 0.032 (2) | 0.041 (2) | 0.0113 (18) | 0.0119 (19) | −0.0014 (18) |
O001 | 0.0362 (13) | 0.0243 (14) | 0.0305 (14) | −0.0054 (10) | 0.0072 (10) | 0.0063 (11) |
O0AA | 0.0379 (14) | 0.0289 (15) | 0.0360 (16) | −0.0040 (11) | 0.0092 (11) | 0.0081 (12) |
O6 | 0.0460 (17) | 0.0337 (18) | 0.050 (2) | 0.0026 (13) | 0.0148 (14) | 0.0096 (14) |
O1AA | 0.0534 (17) | 0.0286 (15) | 0.0371 (16) | −0.0121 (13) | −0.0012 (13) | 0.0056 (13) |
O003 | 0.0528 (18) | 0.0330 (17) | 0.0443 (19) | −0.0089 (13) | 0.0061 (14) | 0.0114 (14) |
O7 | 0.0465 (17) | 0.0253 (16) | 0.064 (2) | 0.0046 (12) | 0.0204 (15) | 0.0067 (15) |
O005 | 0.071 (2) | 0.0233 (15) | 0.0376 (17) | −0.0072 (13) | 0.0184 (14) | −0.0013 (12) |
O2 | 0.0603 (19) | 0.0236 (16) | 0.0507 (19) | −0.0013 (13) | 0.0084 (15) | 0.0101 (14) |
O1 | 0.0517 (18) | 0.0347 (18) | 0.0453 (19) | 0.0078 (14) | 0.0119 (14) | 0.0152 (15) |
N00A | 0.0356 (15) | 0.0232 (16) | 0.0271 (16) | −0.0007 (12) | 0.0128 (12) | 0.0057 (12) |
C00B | 0.0317 (16) | 0.0225 (17) | 0.0310 (19) | 0.0043 (13) | 0.0077 (14) | 0.0006 (15) |
N00C | 0.0356 (15) | 0.0220 (15) | 0.0266 (15) | −0.0038 (12) | 0.0090 (12) | −0.0022 (12) |
N00E | 0.0414 (17) | 0.0172 (15) | 0.0314 (17) | −0.0008 (11) | 0.0158 (13) | 0.0010 (12) |
N00L | 0.0362 (16) | 0.0153 (14) | 0.0312 (17) | −0.0037 (11) | 0.0127 (12) | 0.0010 (12) |
C00M | 0.0371 (19) | 0.0252 (19) | 0.0299 (19) | −0.0065 (14) | 0.0137 (15) | −0.0030 (15) |
C00R | 0.043 (2) | 0.0265 (19) | 0.0271 (18) | −0.0043 (15) | 0.0139 (15) | 0.0042 (15) |
C00S | 0.048 (2) | 0.0205 (17) | 0.0314 (19) | −0.0057 (15) | 0.0224 (16) | −0.0008 (15) |
C00T | 0.055 (2) | 0.0235 (19) | 0.033 (2) | −0.0066 (17) | 0.0106 (17) | −0.0006 (16) |
C00U | 0.0377 (18) | 0.0231 (18) | 0.0305 (19) | −0.0010 (14) | 0.0143 (15) | −0.0013 (15) |
C00V | 0.052 (2) | 0.0185 (18) | 0.036 (2) | −0.0012 (16) | 0.0016 (17) | −0.0028 (16) |
C00W | 0.047 (2) | 0.0219 (18) | 0.031 (2) | −0.0046 (15) | 0.0021 (16) | −0.0071 (15) |
C00Y | 0.052 (2) | 0.026 (2) | 0.043 (2) | −0.0048 (17) | 0.0163 (19) | 0.0086 (18) |
C8 | 0.048 (2) | 0.027 (2) | 0.038 (2) | 0.0094 (17) | 0.0180 (18) | 0.0036 (17) |
C010 | 0.045 (2) | 0.031 (2) | 0.037 (2) | −0.0086 (17) | 0.0094 (17) | 0.0072 (18) |
C011 | 0.047 (2) | 0.029 (2) | 0.030 (2) | 0.0038 (16) | 0.0027 (16) | −0.0013 (16) |
C5 | 0.060 (3) | 0.026 (2) | 0.029 (2) | −0.0023 (18) | 0.0069 (18) | 0.0048 (17) |
C013 | 0.043 (2) | 0.038 (2) | 0.030 (2) | −0.0051 (18) | 0.0047 (16) | −0.0017 (18) |
C014 | 0.043 (2) | 0.0216 (17) | 0.036 (2) | −0.0009 (14) | 0.0208 (16) | 0.0014 (15) |
C015 | 0.040 (2) | 0.048 (3) | 0.035 (2) | −0.0077 (19) | 0.0117 (17) | −0.009 (2) |
C016 | 0.041 (2) | 0.032 (2) | 0.028 (2) | −0.0062 (16) | 0.0018 (16) | −0.0021 (17) |
C017 | 0.051 (3) | 0.030 (2) | 0.055 (3) | 0.0073 (19) | −0.008 (2) | −0.008 (2) |
C018 | 0.0338 (18) | 0.031 (2) | 0.0282 (19) | −0.0018 (14) | 0.0104 (14) | 0.0033 (16) |
C019 | 0.043 (2) | 0.0236 (19) | 0.040 (2) | −0.0001 (15) | 0.0014 (17) | −0.0094 (17) |
C01A | 0.064 (3) | 0.024 (2) | 0.068 (4) | 0.002 (2) | −0.017 (3) | 0.004 (2) |
C01B | 0.069 (3) | 0.026 (2) | 0.035 (2) | −0.0104 (19) | 0.0133 (19) | 0.0043 (17) |
C01C | 0.0401 (19) | 0.0222 (17) | 0.0263 (18) | −0.0051 (14) | 0.0099 (14) | −0.0007 (14) |
O1D | 0.063 (2) | 0.0240 (16) | 0.056 (2) | −0.0049 (13) | 0.0279 (16) | −0.0067 (14) |
C01F | 0.069 (3) | 0.023 (2) | 0.048 (3) | −0.008 (2) | −0.006 (2) | 0.0080 (19) |
C1F | 0.042 (2) | 0.030 (2) | 0.035 (2) | 0.0015 (15) | 0.0109 (16) | 0.0054 (17) |
C01G | 0.039 (2) | 0.043 (3) | 0.039 (2) | −0.0034 (18) | 0.0060 (17) | −0.013 (2) |
C1G | 0.0326 (16) | 0.0226 (17) | 0.0270 (18) | 0.0001 (14) | 0.0066 (13) | 0.0019 (14) |
C01H | 0.0324 (17) | 0.0217 (17) | 0.034 (2) | 0.0032 (13) | 0.0111 (14) | 0.0023 (15) |
C3 | 0.052 (2) | 0.037 (2) | 0.035 (2) | 0.0024 (19) | 0.0029 (18) | 0.0027 (18) |
C9 | 0.051 (2) | 0.0199 (18) | 0.0299 (19) | 0.0061 (16) | 0.0139 (17) | 0.0022 (15) |
C01J | 0.038 (2) | 0.042 (3) | 0.048 (3) | −0.0005 (18) | 0.0082 (19) | −0.018 (2) |
C1J | 0.0352 (18) | 0.0210 (17) | 0.037 (2) | −0.0004 (13) | 0.0072 (15) | −0.0016 (15) |
C01K | 0.042 (2) | 0.035 (2) | 0.038 (2) | 0.0049 (16) | 0.0027 (17) | −0.0002 (18) |
C11 | 0.066 (3) | 0.035 (2) | 0.034 (2) | 0.012 (2) | 0.009 (2) | 0.0044 (18) |
C01M | 0.0373 (18) | 0.0220 (18) | 0.0289 (18) | −0.0002 (13) | 0.0136 (14) | 0.0014 (14) |
C01N | 0.064 (3) | 0.029 (2) | 0.032 (2) | −0.0152 (19) | −0.0022 (19) | 0.0045 (17) |
C1N | 0.0362 (19) | 0.029 (2) | 0.047 (3) | −0.0026 (15) | 0.0028 (17) | −0.0012 (18) |
C01O | 0.041 (2) | 0.033 (2) | 0.030 (2) | −0.0057 (16) | 0.0035 (16) | −0.0072 (17) |
C01P | 0.042 (2) | 0.0208 (18) | 0.035 (2) | −0.0013 (14) | 0.0021 (16) | −0.0091 (15) |
C7 | 0.057 (3) | 0.023 (2) | 0.032 (2) | 0.0065 (17) | 0.0165 (18) | −0.0005 (16) |
C01Q | 0.0333 (18) | 0.028 (2) | 0.046 (2) | 0.0008 (14) | 0.0101 (16) | −0.0005 (18) |
C1Q | 0.040 (2) | 0.0207 (18) | 0.033 (2) | −0.0010 (14) | 0.0140 (15) | 0.0017 (15) |
C01R | 0.044 (2) | 0.043 (3) | 0.029 (2) | −0.0036 (19) | 0.0050 (17) | −0.0001 (19) |
C01S | 0.049 (2) | 0.026 (2) | 0.043 (3) | 0.0028 (17) | −0.0001 (19) | −0.0157 (18) |
C01T | 0.075 (3) | 0.020 (2) | 0.046 (3) | 0.0029 (19) | −0.002 (2) | 0.0000 (19) |
C1 | 0.056 (2) | 0.0238 (19) | 0.0249 (18) | 0.0036 (17) | 0.0151 (16) | −0.0040 (15) |
C01V | 0.046 (2) | 0.042 (3) | 0.034 (2) | −0.0050 (19) | 0.0103 (17) | −0.002 (2) |
C01W | 0.0396 (19) | 0.0232 (18) | 0.033 (2) | 0.0026 (14) | 0.0047 (15) | 0.0031 (15) |
C12 | 0.081 (3) | 0.0212 (19) | 0.026 (2) | 0.0088 (19) | 0.007 (2) | 0.0008 (16) |
C2 | 0.058 (3) | 0.027 (2) | 0.032 (2) | −0.0032 (17) | 0.0045 (18) | 0.0025 (16) |
C01Z | 0.0320 (16) | 0.0221 (17) | 0.038 (2) | 0.0048 (14) | 0.0126 (14) | 0.0016 (16) |
C020 | 0.051 (2) | 0.0229 (19) | 0.040 (2) | −0.0069 (17) | −0.0005 (18) | −0.0037 (17) |
C021 | 0.048 (2) | 0.026 (2) | 0.065 (3) | 0.0044 (18) | −0.007 (2) | −0.009 (2) |
C022 | 0.042 (2) | 0.0202 (17) | 0.036 (2) | −0.0065 (14) | 0.0063 (16) | −0.0012 (15) |
C13 | 0.074 (3) | 0.031 (2) | 0.027 (2) | −0.013 (2) | 0.013 (2) | −0.0028 (18) |
C024 | 0.063 (3) | 0.0219 (19) | 0.033 (2) | −0.0105 (17) | 0.0153 (18) | 0.0031 (16) |
C025 | 0.0360 (18) | 0.031 (2) | 0.039 (2) | 0.0056 (15) | 0.0019 (16) | −0.0110 (17) |
C026 | 0.072 (3) | 0.026 (2) | 0.057 (3) | 0.011 (2) | −0.010 (2) | 0.001 (2) |
O3 | 0.051 (4) | 0.034 (3) | 0.042 (3) | 0.000 (3) | 0.002 (3) | 0.002 (3) |
C6A—O4 | 1.341 (6) | C011—H011 | 0.9300 |
C6A—C1 | 1.386 (6) | C5—H5A | 0.9300 |
C6A—C5 | 1.409 (6) | C5—H5B | 0.9300 |
C4A—C3 | 1.381 (7) | C013—C01O | 1.378 (6) |
C4A—C5 | 1.384 (6) | C013—C01V | 1.406 (6) |
C4A—H4A | 0.9300 | C013—H013 | 0.9300 |
C14A—O5 | 1.325 (6) | C014—H01K | 0.9700 |
C14A—C9 | 1.403 (6) | C014—H01L | 0.9700 |
C14A—C13 | 1.407 (7) | C015—C01J | 1.363 (7) |
C10A—O8 | 1.141 (9) | C015—C01R | 1.404 (6) |
C10A—C9 | 1.389 (6) | C015—H015 | 0.9300 |
C10A—C11 | 1.391 (7) | C016—C01R | 1.367 (6) |
O4—H4 | 0.8200 | C016—C01P | 1.422 (6) |
O5—H5 | 0.8200 | C016—H016 | 0.9300 |
O8—H8 | 0.8200 | C017—C01A | 1.341 (8) |
C6B—C1 | 1.386 (6) | C017—C01S | 1.452 (7) |
C6B—C5 | 1.409 (6) | C017—H017 | 0.9300 |
C6B—H6B | 0.9300 | C018—C01M | 1.497 (6) |
C4B—O3 | 1.344 (8) | C018—H01M | 0.9700 |
C4B—C3 | 1.381 (7) | C018—H01N | 0.9700 |
C4B—C5 | 1.384 (6) | C019—C021 | 1.411 (7) |
C14B—C9 | 1.403 (6) | C019—C01P | 1.421 (6) |
C14B—C13 | 1.407 (7) | C019—C01J | 1.429 (7) |
C14B—H14B | 0.9300 | C01A—C01F | 1.410 (8) |
C10B—C9 | 1.389 (6) | C01A—H01D | 0.9300 |
C10B—C11 | 1.391 (7) | C01B—C024 | 1.517 (7) |
C10B—H10B | 0.9300 | C01B—H01P | 0.9700 |
O001—C00B | 1.374 (5) | C01B—H01Q | 0.9700 |
O001—C010 | 1.436 (5) | C01C—H01E | 0.9700 |
O0AA—C01H | 1.356 (5) | C01C—H01F | 0.9700 |
O0AA—C00Y | 1.432 (5) | O1D—C024 | 1.415 (6) |
O6—C8 | 1.273 (6) | O1D—H1D | 0.8200 |
O1AA—C020 | 1.357 (6) | C01F—C020 | 1.357 (7) |
O1AA—C01N | 1.431 (5) | C01F—H01G | 0.9300 |
O003—C00V | 1.365 (6) | C1F—C01Z | 1.385 (6) |
O003—C01B | 1.427 (5) | C1F—C01K | 1.397 (6) |
O7—C8 | 1.243 (6) | C1F—H1F | 0.9300 |
O005—C00T | 1.415 (6) | C01G—C01V | 1.383 (7) |
O005—H005 | 0.8200 | C01G—C01S | 1.390 (7) |
O2—C7 | 1.262 (6) | C01G—H01H | 0.9300 |
O1—C7 | 1.268 (6) | C1G—C01W | 1.393 (6) |
N00A—C01Z | 1.428 (5) | C01H—C01Q | 1.393 (6) |
N00A—C018 | 1.467 (5) | C01H—C01Z | 1.424 (6) |
N00A—C014 | 1.476 (5) | C3—C2 | 1.379 (7) |
C00B—C1J | 1.387 (6) | C3—H3A | 0.9300 |
C00B—C1G | 1.412 (5) | C3—H3B | 0.9300 |
N00C—C1G | 1.429 (5) | C01J—H01R | 0.9300 |
N00C—C00R | 1.457 (5) | C1J—C025 | 1.395 (6) |
N00C—C00U | 1.468 (5) | C1J—H1J | 0.9300 |
N00E—C1Q | 1.490 (5) | C01K—C1N | 1.382 (7) |
N00E—C00S | 1.492 (5) | C01K—H01S | 0.9300 |
N00E—C01M | 1.517 (6) | C11—C12 | 1.371 (8) |
N00E—H00G | 0.9800 | C11—H11 | 0.9300 |
N00L—C00M | 1.484 (6) | C11—H11A | 0.9300 |
N00L—C022 | 1.498 (5) | C01M—H01T | 0.9700 |
N00L—C01C | 1.500 (5) | C01M—H01U | 0.9700 |
N00L—H00L | 0.9800 | C01N—H01I | 0.9700 |
C00M—C00R | 1.518 (6) | C01N—H01J | 0.9700 |
C00M—H00A | 0.9700 | C1N—C01Q | 1.388 (7) |
C00M—H00B | 0.9700 | C1N—H1N | 0.9300 |
C00R—H00C | 0.9700 | C01O—H01O | 0.9300 |
C00R—H00D | 0.9700 | C7—C1 | 1.493 (6) |
C00S—C014 | 1.494 (6) | C01Q—H01X | 0.9300 |
C00S—H00H | 0.9700 | C1Q—C024 | 1.527 (6) |
C00S—H00I | 0.9700 | C1Q—H1QA | 0.9700 |
C00T—C01N | 1.514 (6) | C1Q—H1QB | 0.9700 |
C00T—C022 | 1.522 (6) | C01R—H01Y | 0.9300 |
C00T—H00T | 0.9800 | C01T—C026 | 1.418 (8) |
C00U—C01C | 1.515 (5) | C01T—H01Z | 0.9300 |
C00U—H00E | 0.9700 | C1—C2 | 1.415 (6) |
C00U—H00F | 0.9700 | C01V—H01V | 0.9300 |
C00V—C01T | 1.382 (7) | C01W—H01W | 0.9300 |
C00V—C01P | 1.415 (6) | C12—C13 | 1.349 (7) |
C00W—C01O | 1.409 (6) | C12—H12 | 0.9300 |
C00W—C01S | 1.419 (6) | C2—H2 | 0.9300 |
C00W—C020 | 1.441 (6) | C021—C026 | 1.382 (8) |
C00Y—H00J | 0.9600 | C021—H021 | 0.9300 |
C00Y—H00K | 0.9600 | C022—H02A | 0.9700 |
C00Y—H00M | 0.9600 | C022—H02B | 0.9700 |
C8—C9 | 1.507 (6) | C13—H13 | 0.9300 |
C010—H01A | 0.9600 | C13—H13A | 0.9300 |
C010—H01B | 0.9600 | C024—H024 | 0.9800 |
C010—H01C | 0.9600 | C025—H025 | 0.9300 |
C011—C025 | 1.377 (6) | C026—H026 | 0.9300 |
C011—C01W | 1.386 (6) | O3—H3 | 0.8200 |
O4—C6A—C1 | 122.5 (4) | O003—C01B—H01Q | 110.4 |
O4—C6A—C5 | 117.3 (4) | C024—C01B—H01Q | 110.4 |
C1—C6A—C5 | 120.2 (4) | H01P—C01B—H01Q | 108.6 |
C3—C4A—C5 | 120.5 (4) | N00L—C01C—C00U | 111.3 (3) |
C3—C4A—H4A | 119.7 | N00L—C01C—H01E | 109.4 |
C5—C4A—H4A | 119.7 | C00U—C01C—H01E | 109.4 |
O5—C14A—C9 | 121.9 (4) | N00L—C01C—H01F | 109.4 |
O5—C14A—C13 | 118.8 (4) | C00U—C01C—H01F | 109.4 |
C9—C14A—C13 | 119.3 (4) | H01E—C01C—H01F | 108.0 |
O8—C10A—C9 | 114.2 (7) | C024—O1D—H1D | 109.5 |
O8—C10A—C11 | 122.6 (7) | C020—C01F—C01A | 119.2 (5) |
C9—C10A—C11 | 122.2 (5) | C020—C01F—H01G | 120.4 |
C6A—O4—H4 | 109.5 | C01A—C01F—H01G | 120.4 |
C14A—O5—H5 | 109.5 | C01Z—C1F—C01K | 122.1 (4) |
C10A—O8—H8 | 109.5 | C01Z—C1F—H1F | 119.0 |
C1—C6B—C5 | 120.2 (4) | C01K—C1F—H1F | 119.0 |
C1—C6B—H6B | 119.9 | C01V—C01G—C01S | 121.0 (4) |
C5—C6B—H6B | 119.9 | C01V—C01G—H01H | 119.5 |
O3—C4B—C3 | 110.5 (5) | C01S—C01G—H01H | 119.5 |
O3—C4B—C5 | 128.9 (5) | C01W—C1G—C00B | 118.3 (4) |
C3—C4B—C5 | 120.5 (4) | C01W—C1G—N00C | 122.8 (4) |
C9—C14B—C13 | 119.3 (4) | C00B—C1G—N00C | 118.7 (3) |
C9—C14B—H14B | 120.3 | O0AA—C01H—C01Q | 124.8 (4) |
C13—C14B—H14B | 120.3 | O0AA—C01H—C01Z | 115.9 (3) |
C9—C10B—C11 | 122.2 (5) | C01Q—C01H—C01Z | 119.3 (4) |
C9—C10B—H10B | 118.9 | C2—C3—C4A | 119.5 (4) |
C11—C10B—H10B | 118.9 | C2—C3—C4B | 119.5 (4) |
C00B—O001—C010 | 116.2 (3) | C2—C3—H3A | 120.3 |
C01H—O0AA—C00Y | 116.9 (3) | C4A—C3—H3A | 120.3 |
C020—O1AA—C01N | 118.8 (4) | C2—C3—H3B | 120.3 |
C00V—O003—C01B | 119.6 (4) | C4B—C3—H3B | 120.3 |
C00T—O005—H005 | 109.5 | C10A—C9—C14A | 117.9 (4) |
C01Z—N00A—C018 | 115.3 (3) | C10B—C9—C14B | 117.9 (4) |
C01Z—N00A—C014 | 115.1 (3) | C10B—C9—C8 | 120.9 (4) |
C018—N00A—C014 | 108.4 (3) | C10A—C9—C8 | 120.9 (4) |
O001—C00B—C1J | 124.3 (4) | C14A—C9—C8 | 121.1 (4) |
O001—C00B—C1G | 115.6 (3) | C14B—C9—C8 | 121.1 (4) |
C1J—C00B—C1G | 120.0 (4) | C015—C01J—C019 | 120.9 (4) |
C1G—N00C—C00R | 115.9 (3) | C015—C01J—H01R | 119.6 |
C1G—N00C—C00U | 114.7 (3) | C019—C01J—H01R | 119.6 |
C00R—N00C—C00U | 108.2 (3) | C00B—C1J—C025 | 120.1 (4) |
C1Q—N00E—C00S | 113.3 (3) | C00B—C1J—H1J | 119.9 |
C1Q—N00E—C01M | 108.4 (3) | C025—C1J—H1J | 119.9 |
C00S—N00E—C01M | 110.5 (3) | C1N—C01K—C1F | 119.1 (4) |
C1Q—N00E—H00G | 108.2 | C1N—C01K—H01S | 120.5 |
C00S—N00E—H00G | 108.2 | C1F—C01K—H01S | 120.5 |
C01M—N00E—H00G | 108.2 | C12—C11—C10A | 118.2 (5) |
C00M—N00L—C022 | 109.3 (3) | C12—C11—C10B | 118.2 (5) |
C00M—N00L—C01C | 111.0 (3) | C12—C11—H11 | 120.9 |
C022—N00L—C01C | 111.0 (3) | C10A—C11—H11 | 120.9 |
C00M—N00L—H00L | 108.5 | C12—C11—H11A | 120.9 |
C022—N00L—H00L | 108.5 | C10B—C11—H11A | 120.9 |
C01C—N00L—H00L | 108.5 | C018—C01M—N00E | 111.8 (3) |
N00L—C00M—C00R | 111.8 (3) | C018—C01M—H01T | 109.3 |
N00L—C00M—H00A | 109.2 | N00E—C01M—H01T | 109.3 |
C00R—C00M—H00A | 109.2 | C018—C01M—H01U | 109.3 |
N00L—C00M—H00B | 109.2 | N00E—C01M—H01U | 109.3 |
C00R—C00M—H00B | 109.2 | H01T—C01M—H01U | 107.9 |
H00A—C00M—H00B | 107.9 | O1AA—C01N—C00T | 106.4 (3) |
N00C—C00R—C00M | 109.5 (3) | O1AA—C01N—H01I | 110.4 |
N00C—C00R—H00C | 109.8 | C00T—C01N—H01I | 110.4 |
C00M—C00R—H00C | 109.8 | O1AA—C01N—H01J | 110.4 |
N00C—C00R—H00D | 109.8 | C00T—C01N—H01J | 110.4 |
C00M—C00R—H00D | 109.8 | H01I—C01N—H01J | 108.6 |
H00C—C00R—H00D | 108.2 | C01K—C1N—C01Q | 120.3 (4) |
N00E—C00S—C014 | 112.6 (3) | C01K—C1N—H1N | 119.9 |
N00E—C00S—H00H | 109.1 | C01Q—C1N—H1N | 119.9 |
C014—C00S—H00H | 109.1 | C013—C01O—C00W | 120.2 (4) |
N00E—C00S—H00I | 109.1 | C013—C01O—H01O | 119.9 |
C014—C00S—H00I | 109.1 | C00W—C01O—H01O | 119.9 |
H00H—C00S—H00I | 107.8 | C00V—C01P—C019 | 119.1 (4) |
O005—C00T—C01N | 112.9 (4) | C00V—C01P—C016 | 121.6 (4) |
O005—C00T—C022 | 110.2 (4) | C019—C01P—C016 | 119.3 (4) |
C01N—C00T—C022 | 109.8 (4) | O2—C7—O1 | 123.3 (4) |
O005—C00T—H00T | 107.9 | O2—C7—C1 | 118.4 (4) |
C01N—C00T—H00T | 107.9 | O1—C7—C1 | 118.3 (4) |
C022—C00T—H00T | 107.9 | C1N—C01Q—C01H | 121.0 (4) |
N00C—C00U—C01C | 110.4 (3) | C1N—C01Q—H01X | 119.5 |
N00C—C00U—H00E | 109.6 | C01H—C01Q—H01X | 119.5 |
C01C—C00U—H00E | 109.6 | N00E—C1Q—C024 | 112.2 (3) |
N00C—C00U—H00F | 109.6 | N00E—C1Q—H1QA | 109.2 |
C01C—C00U—H00F | 109.6 | C024—C1Q—H1QA | 109.2 |
H00E—C00U—H00F | 108.1 | N00E—C1Q—H1QB | 109.2 |
O003—C00V—C01T | 124.8 (4) | C024—C1Q—H1QB | 109.2 |
O003—C00V—C01P | 114.3 (4) | H1QA—C1Q—H1QB | 107.9 |
C01T—C00V—C01P | 120.9 (5) | C016—C01R—C015 | 120.2 (5) |
C01O—C00W—C01S | 119.7 (4) | C016—C01R—H01Y | 119.9 |
C01O—C00W—C020 | 121.5 (4) | C015—C01R—H01Y | 119.9 |
C01S—C00W—C020 | 118.8 (4) | C01G—C01S—C00W | 118.9 (4) |
O0AA—C00Y—H00J | 109.5 | C01G—C01S—C017 | 122.9 (4) |
O0AA—C00Y—H00K | 109.5 | C00W—C01S—C017 | 118.0 (5) |
H00J—C00Y—H00K | 109.5 | C00V—C01T—C026 | 119.1 (5) |
O0AA—C00Y—H00M | 109.5 | C00V—C01T—H01Z | 120.4 |
H00J—C00Y—H00M | 109.5 | C026—C01T—H01Z | 120.4 |
H00K—C00Y—H00M | 109.5 | C6B—C1—C2 | 118.2 (4) |
O7—C8—O6 | 123.3 (4) | C6A—C1—C2 | 118.2 (4) |
O7—C8—C9 | 119.3 (4) | C6B—C1—C7 | 121.3 (4) |
O6—C8—C9 | 117.4 (4) | C6A—C1—C7 | 121.3 (4) |
O001—C010—H01A | 109.5 | C2—C1—C7 | 120.5 (4) |
O001—C010—H01B | 109.5 | C01G—C01V—C013 | 120.1 (5) |
H01A—C010—H01B | 109.5 | C01G—C01V—H01V | 119.9 |
O001—C010—H01C | 109.5 | C013—C01V—H01V | 119.9 |
H01A—C010—H01C | 109.5 | C011—C01W—C1G | 121.6 (4) |
H01B—C010—H01C | 109.5 | C011—C01W—H01W | 119.2 |
C025—C011—C01W | 119.5 (4) | C1G—C01W—H01W | 119.2 |
C025—C011—H011 | 120.3 | C13—C12—C11 | 121.9 (5) |
C01W—C011—H011 | 120.3 | C13—C12—H12 | 119.0 |
C4A—C5—C6A | 120.1 (4) | C11—C12—H12 | 119.0 |
C4B—C5—C6B | 120.1 (4) | C3—C2—C1 | 121.6 (4) |
C4A—C5—H5A | 120.0 | C3—C2—H2 | 119.2 |
C6A—C5—H5A | 120.0 | C1—C2—H2 | 119.2 |
C4B—C5—H5B | 120.0 | C1F—C01Z—C01H | 118.3 (4) |
C6B—C5—H5B | 120.0 | C1F—C01Z—N00A | 123.8 (4) |
C01O—C013—C01V | 120.0 (4) | C01H—C01Z—N00A | 117.9 (4) |
C01O—C013—H013 | 120.0 | C01F—C020—O1AA | 125.2 (5) |
C01V—C013—H013 | 120.0 | C01F—C020—C00W | 121.0 (5) |
N00A—C014—C00S | 109.6 (3) | O1AA—C020—C00W | 113.7 (4) |
N00A—C014—H01K | 109.8 | C026—C021—C019 | 119.7 (5) |
C00S—C014—H01K | 109.8 | C026—C021—H021 | 120.1 |
N00A—C014—H01L | 109.8 | C019—C021—H021 | 120.1 |
C00S—C014—H01L | 109.8 | N00L—C022—C00T | 115.2 (4) |
H01K—C014—H01L | 108.2 | N00L—C022—H02A | 108.5 |
C01J—C015—C01R | 120.7 (5) | C00T—C022—H02A | 108.5 |
C01J—C015—H015 | 119.6 | N00L—C022—H02B | 108.5 |
C01R—C015—H015 | 119.6 | C00T—C022—H02B | 108.5 |
C01R—C016—C01P | 120.6 (4) | H02A—C022—H02B | 107.5 |
C01R—C016—H016 | 119.7 | C12—C13—C14A | 120.4 (4) |
C01P—C016—H016 | 119.7 | C12—C13—C14B | 120.4 (4) |
C01A—C017—C01S | 120.0 (5) | C12—C13—H13 | 119.8 |
C01A—C017—H017 | 120.0 | C14A—C13—H13 | 119.8 |
C01S—C017—H017 | 120.0 | C12—C13—H13A | 119.8 |
N00A—C018—C01M | 109.5 (3) | C14B—C13—H13A | 119.8 |
N00A—C018—H01M | 109.8 | O1D—C024—C01B | 112.2 (4) |
C01M—C018—H01M | 109.8 | O1D—C024—C1Q | 111.7 (4) |
N00A—C018—H01N | 109.8 | C01B—C024—C1Q | 109.4 (4) |
C01M—C018—H01N | 109.8 | O1D—C024—H024 | 107.8 |
H01M—C018—H01N | 108.2 | C01B—C024—H024 | 107.8 |
C021—C019—C01P | 119.6 (5) | C1Q—C024—H024 | 107.8 |
C021—C019—C01J | 122.2 (4) | C011—C025—C1J | 120.5 (4) |
C01P—C019—C01J | 118.1 (4) | C011—C025—H025 | 119.8 |
C017—C01A—C01F | 122.5 (5) | C1J—C025—H025 | 119.8 |
C017—C01A—H01D | 118.7 | C021—C026—C01T | 121.2 (5) |
C01F—C01A—H01D | 118.7 | C021—C026—H026 | 119.4 |
O003—C01B—C024 | 106.6 (4) | C01T—C026—H026 | 119.4 |
O003—C01B—H01P | 110.4 | C4B—O3—H3 | 109.5 |
C024—C01B—H01P | 110.4 |
C31H34N2O6.49 | F(000) = 1144 |
Mr = 538.44 | Dx = 1.348 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.279 (5) Å | Cell parameters from 9947 reflections |
b = 17.633 (7) Å | θ = 2.6–26.4° |
c = 13.377 (6) Å | µ = 0.10 mm−1 |
β = 94.51 (2)° | T = 100 K |
V = 2652.2 (18) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.15 × 0.10 mm |
Bruker APEX-II CCD diffractometer | 4387 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.054 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0984 before and 0.0585 after correction. The Ratio of minimum to maximum transmission is 0.8654. The λ/2 correction factor is Not present. | θmax = 26.3°, θmin = 2.2° |
Tmin = 0.645, Tmax = 0.745 | h = −14→14 |
31190 measured reflections | k = −21→21 |
5299 independent reflections | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.072 | H-atom parameters constrained |
wR(F2) = 0.162 | w = 1/[σ2(Fo2) + 4.4821P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max < 0.001 |
5299 reflections | Δρmax = 0.28 e Å−3 |
385 parameters | Δρmin = −0.24 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C3A | 0.4524 (3) | 0.45867 (17) | 0.1032 (2) | 0.0367 (7) | 0.88 |
C4A | 0.4790 (3) | 0.52778 (17) | 0.1534 (2) | 0.0375 (7) | 0.73 |
H4A | 0.418665 | 0.564907 | 0.158210 | 0.045* | 0.73 |
C5A | 0.5919 (3) | 0.54126 (17) | 0.1953 (2) | 0.0393 (7) | 0.86 |
H5A | 0.608931 | 0.587857 | 0.229105 | 0.047* | 0.86 |
C7A | 0.6559 (3) | 0.42064 (18) | 0.1391 (2) | 0.0405 (7) | 0.8 |
H7A | 0.717186 | 0.384154 | 0.134449 | 0.049* | 0.8 |
O3A | 0.3408 (2) | 0.44847 (16) | 0.0651 (2) | 0.0470 (7) | 0.88 |
H3A | 0.334916 | 0.406151 | 0.036289 | 0.070* | 0.88 |
C3B | 0.4524 (3) | 0.45867 (17) | 0.1032 (2) | 0.0367 (7) | 0.12 |
H3B | 0.373950 | 0.448873 | 0.075141 | 0.044* | 0.12 |
C4B | 0.4790 (3) | 0.52778 (17) | 0.1534 (2) | 0.0375 (7) | 0.27 |
C5B | 0.5919 (3) | 0.54126 (17) | 0.1953 (2) | 0.0393 (7) | 0.14 |
C7B | 0.6559 (3) | 0.42064 (18) | 0.1391 (2) | 0.0405 (7) | 0.2 |
O4A | 0.3927 (7) | 0.5737 (4) | 0.1543 (5) | 0.0355 (17) | 0.27 |
H4AA | 0.335745 | 0.557872 | 0.115684 | 0.053* | 0.27 |
O5 | 0.6376 (12) | 0.5992 (7) | 0.2520 (9) | 0.027 (3) | 0.14 |
H5 | 0.607889 | 0.640263 | 0.230241 | 0.040* | 0.14 |
O7 | 0.7182 (11) | 0.3725 (7) | 0.1425 (10) | 0.058 (4) | 0.2 |
H7 | 0.751932 | 0.369162 | 0.200586 | 0.087* | 0.2 |
C1 | 0.5166 (3) | 0.33290 (17) | 0.0367 (2) | 0.0392 (7) | |
C2 | 0.5413 (3) | 0.40511 (16) | 0.0951 (2) | 0.0346 (7) | |
C6 | 0.6812 (3) | 0.48846 (18) | 0.1893 (2) | 0.0417 (7) | |
H6A | 0.758929 | 0.498282 | 0.219051 | 0.050* | 0.8 |
H6B | 0.758929 | 0.498282 | 0.219051 | 0.050* | 0.2 |
O1 | 0.4116 (2) | 0.32408 (12) | −0.00501 (18) | 0.0472 (6) | |
O2 | 0.5981 (2) | 0.28568 (12) | 0.03037 (18) | 0.0461 (6) | |
C8 | 0.1434 (3) | 0.37968 (16) | 0.5968 (2) | 0.0366 (7) | |
H8A | 0.143119 | 0.333917 | 0.555191 | 0.055* | |
H8B | 0.061313 | 0.394016 | 0.607279 | 0.055* | |
H8C | 0.186982 | 0.369664 | 0.661700 | 0.055* | |
C9 | 0.1492 (2) | 0.46093 (15) | 0.4543 (2) | 0.0273 (6) | |
C10 | 0.0511 (2) | 0.42579 (15) | 0.4056 (2) | 0.0311 (6) | |
H10 | 0.012754 | 0.385670 | 0.437730 | 0.037* | |
C11 | 0.0082 (3) | 0.44873 (16) | 0.3098 (2) | 0.0342 (6) | |
H11 | −0.059332 | 0.424387 | 0.277142 | 0.041* | |
C12 | 0.0637 (3) | 0.50677 (16) | 0.2622 (2) | 0.0349 (7) | |
H12 | 0.034867 | 0.522321 | 0.196708 | 0.042* | |
C13 | 0.1624 (3) | 0.54239 (15) | 0.3111 (2) | 0.0323 (6) | |
H13 | 0.200238 | 0.582258 | 0.277960 | 0.039* | |
C14 | 0.2069 (2) | 0.52108 (14) | 0.4072 (2) | 0.0269 (6) | |
C15 | 0.2880 (3) | 0.59834 (15) | 0.5481 (2) | 0.0298 (6) | |
H15A | 0.233736 | 0.569606 | 0.588840 | 0.036* | |
H15B | 0.249073 | 0.646960 | 0.528165 | 0.036* | |
C16 | 0.4036 (3) | 0.61373 (15) | 0.6096 (2) | 0.0294 (6) | |
H16A | 0.387625 | 0.644905 | 0.668634 | 0.035* | |
H16B | 0.438574 | 0.565071 | 0.634336 | 0.035* | |
C17 | 0.5027 (3) | 0.61475 (15) | 0.4513 (2) | 0.0299 (6) | |
H17A | 0.551639 | 0.646412 | 0.409371 | 0.036* | |
H17B | 0.544324 | 0.565806 | 0.463650 | 0.036* | |
C18 | 0.3835 (3) | 0.60047 (16) | 0.3957 (2) | 0.0311 (6) | |
H18A | 0.343175 | 0.649344 | 0.379517 | 0.037* | |
H18B | 0.394329 | 0.573703 | 0.331968 | 0.037* | |
C19 | 0.6108 (3) | 0.66002 (15) | 0.6056 (2) | 0.0302 (6) | |
H19A | 0.664199 | 0.688342 | 0.563677 | 0.036* | |
H19B | 0.643855 | 0.608354 | 0.615871 | 0.036* | |
C20 | 0.6101 (3) | 0.69923 (16) | 0.7071 (2) | 0.0371 (7) | |
H20 | 0.566673 | 0.665446 | 0.751935 | 0.045* | |
C21 | 0.7359 (3) | 0.70820 (17) | 0.7540 (2) | 0.0410 (7) | |
H21A | 0.735350 | 0.728841 | 0.822787 | 0.049* | |
H21B | 0.777216 | 0.658624 | 0.757378 | 0.049* | |
C22 | 0.9158 (3) | 0.76517 (15) | 0.7013 (2) | 0.0346 (7) | |
C23 | 0.9877 (3) | 0.73277 (16) | 0.7773 (2) | 0.0451 (8) | |
H23 | 0.953868 | 0.706151 | 0.829835 | 0.054* | |
C24 | 1.1123 (3) | 0.73946 (18) | 0.7763 (3) | 0.0508 (9) | |
H24 | 1.161765 | 0.717526 | 0.829363 | 0.061* | |
C25 | 1.1635 (3) | 0.77654 (17) | 0.7014 (3) | 0.0443 (8) | |
H25 | 1.247530 | 0.777088 | 0.699812 | 0.053* | |
C26 | 1.0899 (3) | 0.81467 (16) | 0.6250 (2) | 0.0358 (7) | |
C27 | 0.9647 (3) | 0.80992 (15) | 0.6260 (2) | 0.0305 (6) | |
C28 | 0.8916 (3) | 0.85116 (16) | 0.5540 (2) | 0.0324 (6) | |
H28 | 0.807547 | 0.846989 | 0.553066 | 0.039* | |
C29 | 0.9411 (3) | 0.89705 (17) | 0.4855 (2) | 0.0353 (7) | |
H29 | 0.891377 | 0.925748 | 0.439005 | 0.042* | |
C30 | 1.0656 (3) | 0.90155 (18) | 0.4842 (2) | 0.0382 (7) | |
H30 | 1.099637 | 0.933077 | 0.436434 | 0.046* | |
C31 | 1.1382 (3) | 0.86046 (18) | 0.5517 (2) | 0.0394 (7) | |
H31 | 1.222042 | 0.862977 | 0.549013 | 0.047* | |
N1 | 0.3106 (2) | 0.55443 (12) | 0.45792 (16) | 0.0267 (5) | |
N2 | 0.4908 (2) | 0.65410 (12) | 0.55003 (16) | 0.0274 (5) | |
H2 | 0.460397 | 0.706598 | 0.535837 | 0.033* | |
O8 | 0.19991 (17) | 0.44034 (10) | 0.54724 (14) | 0.0317 (4) | |
O9 | 0.5477 (2) | 0.76891 (11) | 0.69866 (17) | 0.0455 (6) | |
H9 | 0.564278 | 0.791355 | 0.646163 | 0.068* | |
O10 | 0.7946 (2) | 0.75984 (11) | 0.69099 (16) | 0.0401 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C3A | 0.0473 (18) | 0.0388 (16) | 0.0250 (14) | −0.0107 (14) | 0.0090 (13) | −0.0033 (12) |
C4A | 0.056 (2) | 0.0301 (15) | 0.0277 (14) | 0.0038 (14) | 0.0084 (13) | −0.0001 (12) |
C5A | 0.065 (2) | 0.0304 (15) | 0.0225 (14) | −0.0120 (14) | 0.0050 (13) | −0.0009 (11) |
C7A | 0.055 (2) | 0.0338 (16) | 0.0327 (15) | −0.0091 (15) | 0.0058 (14) | 0.0024 (12) |
O3A | 0.0432 (15) | 0.0514 (16) | 0.0470 (15) | −0.0046 (12) | 0.0079 (12) | −0.0204 (12) |
C3B | 0.0473 (18) | 0.0388 (16) | 0.0250 (14) | −0.0107 (14) | 0.0090 (13) | −0.0033 (12) |
C4B | 0.056 (2) | 0.0301 (15) | 0.0277 (14) | 0.0038 (14) | 0.0084 (13) | −0.0001 (12) |
C5B | 0.065 (2) | 0.0304 (15) | 0.0225 (14) | −0.0120 (14) | 0.0050 (13) | −0.0009 (11) |
C7B | 0.055 (2) | 0.0338 (16) | 0.0327 (15) | −0.0091 (15) | 0.0058 (14) | 0.0024 (12) |
O4A | 0.038 (4) | 0.042 (4) | 0.026 (4) | 0.009 (3) | −0.002 (3) | −0.005 (3) |
O5 | 0.038 (8) | 0.015 (6) | 0.026 (6) | −0.006 (5) | −0.002 (6) | −0.007 (5) |
O7 | 0.045 (7) | 0.047 (7) | 0.080 (9) | 0.041 (6) | −0.016 (6) | −0.028 (6) |
C1 | 0.054 (2) | 0.0304 (15) | 0.0356 (16) | −0.0143 (14) | 0.0177 (14) | −0.0016 (12) |
C2 | 0.0519 (18) | 0.0251 (13) | 0.0288 (14) | −0.0074 (13) | 0.0156 (13) | −0.0010 (11) |
C6 | 0.054 (2) | 0.0380 (17) | 0.0331 (16) | −0.0032 (15) | 0.0035 (14) | 0.0004 (13) |
O1 | 0.0532 (14) | 0.0373 (12) | 0.0531 (14) | −0.0105 (10) | 0.0156 (11) | −0.0167 (10) |
O2 | 0.0596 (15) | 0.0259 (10) | 0.0547 (14) | −0.0032 (10) | 0.0157 (11) | −0.0069 (10) |
C8 | 0.0433 (17) | 0.0287 (14) | 0.0390 (16) | −0.0049 (13) | 0.0116 (13) | 0.0071 (12) |
C9 | 0.0289 (14) | 0.0229 (13) | 0.0312 (14) | 0.0051 (10) | 0.0085 (11) | 0.0006 (11) |
C10 | 0.0306 (14) | 0.0233 (13) | 0.0403 (16) | 0.0018 (11) | 0.0087 (12) | −0.0014 (11) |
C11 | 0.0342 (15) | 0.0292 (14) | 0.0390 (16) | 0.0028 (12) | 0.0011 (12) | −0.0070 (12) |
C12 | 0.0407 (17) | 0.0319 (15) | 0.0321 (15) | 0.0068 (12) | 0.0027 (12) | −0.0017 (12) |
C13 | 0.0410 (16) | 0.0249 (13) | 0.0320 (14) | 0.0029 (12) | 0.0092 (12) | 0.0023 (11) |
C14 | 0.0296 (14) | 0.0218 (12) | 0.0304 (14) | 0.0026 (11) | 0.0091 (11) | 0.0000 (10) |
C15 | 0.0380 (15) | 0.0234 (13) | 0.0300 (14) | 0.0005 (11) | 0.0153 (12) | −0.0006 (11) |
C16 | 0.0413 (16) | 0.0224 (13) | 0.0262 (13) | −0.0053 (11) | 0.0138 (12) | −0.0019 (10) |
C17 | 0.0398 (16) | 0.0231 (13) | 0.0290 (14) | −0.0017 (11) | 0.0170 (12) | −0.0011 (11) |
C18 | 0.0390 (16) | 0.0296 (14) | 0.0259 (13) | −0.0034 (12) | 0.0112 (12) | 0.0022 (11) |
C19 | 0.0384 (16) | 0.0207 (12) | 0.0327 (14) | −0.0033 (11) | 0.0098 (12) | 0.0005 (11) |
C20 | 0.056 (2) | 0.0232 (13) | 0.0336 (15) | −0.0085 (13) | 0.0144 (14) | 0.0002 (11) |
C21 | 0.064 (2) | 0.0270 (14) | 0.0321 (15) | −0.0128 (14) | 0.0044 (14) | 0.0030 (12) |
C22 | 0.0483 (18) | 0.0190 (13) | 0.0361 (15) | −0.0024 (12) | 0.0001 (13) | −0.0050 (11) |
C23 | 0.068 (2) | 0.0222 (14) | 0.0431 (18) | −0.0005 (14) | −0.0050 (16) | 0.0025 (13) |
C24 | 0.066 (2) | 0.0248 (15) | 0.059 (2) | 0.0098 (15) | −0.0116 (18) | 0.0021 (14) |
C25 | 0.0447 (19) | 0.0288 (15) | 0.058 (2) | 0.0088 (13) | −0.0048 (15) | −0.0077 (14) |
C26 | 0.0432 (17) | 0.0247 (14) | 0.0390 (16) | 0.0054 (12) | 0.0007 (13) | −0.0133 (12) |
C27 | 0.0393 (16) | 0.0214 (12) | 0.0304 (14) | −0.0018 (11) | 0.0011 (12) | −0.0089 (11) |
C28 | 0.0356 (16) | 0.0335 (15) | 0.0282 (14) | −0.0044 (12) | 0.0033 (12) | −0.0057 (11) |
C29 | 0.0379 (16) | 0.0394 (16) | 0.0286 (14) | −0.0035 (13) | 0.0030 (12) | −0.0016 (12) |
C30 | 0.0394 (17) | 0.0449 (17) | 0.0311 (15) | −0.0048 (14) | 0.0082 (13) | −0.0051 (13) |
C31 | 0.0324 (16) | 0.0430 (17) | 0.0436 (17) | −0.0005 (13) | 0.0070 (13) | −0.0147 (14) |
N1 | 0.0337 (12) | 0.0231 (11) | 0.0246 (11) | −0.0014 (9) | 0.0104 (9) | −0.0003 (9) |
N2 | 0.0391 (13) | 0.0166 (10) | 0.0279 (11) | −0.0012 (9) | 0.0112 (10) | −0.0013 (8) |
O8 | 0.0387 (11) | 0.0260 (9) | 0.0310 (10) | −0.0046 (8) | 0.0068 (8) | 0.0075 (8) |
O9 | 0.0683 (16) | 0.0250 (10) | 0.0457 (13) | −0.0040 (10) | 0.0208 (11) | −0.0065 (9) |
O10 | 0.0487 (13) | 0.0318 (11) | 0.0399 (12) | −0.0096 (9) | 0.0032 (10) | 0.0086 (9) |
C3A—O3A | 1.333 (4) | C15—N1 | 1.473 (3) |
C3A—C2 | 1.387 (4) | C15—C16 | 1.512 (4) |
C3A—C4A | 1.412 (4) | C15—H15A | 0.9900 |
C4A—C5A | 1.371 (5) | C15—H15B | 0.9900 |
C4A—H4A | 0.9500 | C16—N2 | 1.494 (3) |
C5A—C6 | 1.378 (5) | C16—H16A | 0.9900 |
C5A—H5A | 0.9500 | C16—H16B | 0.9900 |
C7A—C6 | 1.390 (4) | C17—C18 | 1.507 (4) |
C7A—C2 | 1.405 (5) | C17—N2 | 1.507 (3) |
C7A—H7A | 0.9500 | C17—H17A | 0.9900 |
O3A—H3A | 0.8400 | C17—H17B | 0.9900 |
C3B—C2 | 1.387 (4) | C18—N1 | 1.461 (3) |
C3B—C4B | 1.412 (4) | C18—H18A | 0.9900 |
C3B—H3B | 0.9500 | C18—H18B | 0.9900 |
C4B—O4A | 1.267 (8) | C19—N2 | 1.496 (4) |
C4B—C5B | 1.371 (5) | C19—C20 | 1.525 (4) |
C5B—O5 | 1.350 (12) | C19—H19A | 0.9900 |
C5B—C6 | 1.378 (5) | C19—H19B | 0.9900 |
C7B—O7 | 1.101 (10) | C20—O9 | 1.416 (4) |
C7B—C6 | 1.390 (4) | C20—C21 | 1.514 (5) |
C7B—C2 | 1.405 (5) | C20—H20 | 1.0000 |
O4A—H4AA | 0.8400 | C21—O10 | 1.437 (3) |
O5—H5 | 0.8400 | C21—H21A | 0.9900 |
O7—H7 | 0.8400 | C21—H21B | 0.9900 |
C1—O2 | 1.248 (4) | C22—O10 | 1.366 (4) |
C1—O1 | 1.278 (4) | C22—C23 | 1.373 (4) |
C1—C2 | 1.508 (4) | C22—C27 | 1.424 (4) |
C6—H6A | 0.9500 | C23—C24 | 1.411 (5) |
C6—H6B | 0.9500 | C23—H23 | 0.9500 |
C8—O8 | 1.434 (3) | C24—C25 | 1.363 (5) |
C8—H8A | 0.9800 | C24—H24 | 0.9500 |
C8—H8B | 0.9800 | C25—C26 | 1.432 (4) |
C8—H8C | 0.9800 | C25—H25 | 0.9500 |
C9—O8 | 1.375 (3) | C26—C31 | 1.412 (5) |
C9—C10 | 1.386 (4) | C26—C27 | 1.416 (4) |
C9—C14 | 1.418 (4) | C27—C28 | 1.419 (4) |
C10—C11 | 1.394 (4) | C28—C29 | 1.374 (4) |
C10—H10 | 0.9500 | C28—H28 | 0.9500 |
C11—C12 | 1.381 (4) | C29—C30 | 1.408 (4) |
C11—H11 | 0.9500 | C29—H29 | 0.9500 |
C12—C13 | 1.395 (4) | C30—C31 | 1.377 (4) |
C12—H12 | 0.9500 | C30—H30 | 0.9500 |
C13—C14 | 1.395 (4) | C31—H31 | 0.9500 |
C13—H13 | 0.9500 | N2—H2 | 1.0000 |
C14—N1 | 1.431 (3) | O9—H9 | 0.8400 |
O3A—C3A—C2 | 123.0 (3) | N2—C16—H16B | 109.3 |
O3A—C3A—C4A | 117.2 (3) | C15—C16—H16B | 109.3 |
C2—C3A—C4A | 119.8 (3) | H16A—C16—H16B | 107.9 |
C5A—C4A—C3A | 120.0 (3) | C18—C17—N2 | 111.8 (2) |
C5A—C4A—H4A | 120.0 | C18—C17—H17A | 109.2 |
C3A—C4A—H4A | 120.0 | N2—C17—H17A | 109.2 |
C4A—C5A—C6 | 121.2 (3) | C18—C17—H17B | 109.2 |
C4A—C5A—H5A | 119.4 | N2—C17—H17B | 109.2 |
C6—C5A—H5A | 119.4 | H17A—C17—H17B | 107.9 |
C6—C7A—C2 | 121.2 (3) | N1—C18—C17 | 109.3 (2) |
C6—C7A—H7A | 119.4 | N1—C18—H18A | 109.8 |
C2—C7A—H7A | 119.4 | C17—C18—H18A | 109.8 |
C3A—O3A—H3A | 109.5 | N1—C18—H18B | 109.8 |
C2—C3B—C4B | 119.8 (3) | C17—C18—H18B | 109.8 |
C2—C3B—H3B | 120.1 | H18A—C18—H18B | 108.3 |
C4B—C3B—H3B | 120.1 | N2—C19—C20 | 114.0 (2) |
O4A—C4B—C5B | 125.1 (4) | N2—C19—H19A | 108.8 |
O4A—C4B—C3B | 114.9 (4) | C20—C19—H19A | 108.8 |
C5B—C4B—C3B | 120.0 (3) | N2—C19—H19B | 108.8 |
O5—C5B—C4B | 131.4 (7) | C20—C19—H19B | 108.8 |
O5—C5B—C6 | 107.2 (6) | H19A—C19—H19B | 107.7 |
C4B—C5B—C6 | 121.2 (3) | O9—C20—C21 | 112.7 (2) |
O7—C7B—C6 | 122.5 (7) | O9—C20—C19 | 111.1 (2) |
O7—C7B—C2 | 115.5 (7) | C21—C20—C19 | 110.2 (3) |
C6—C7B—C2 | 121.2 (3) | O9—C20—H20 | 107.5 |
C4B—O4A—H4AA | 109.5 | C21—C20—H20 | 107.5 |
C5B—O5—H5 | 109.5 | C19—C20—H20 | 107.5 |
C7B—O7—H7 | 109.5 | O10—C21—C20 | 106.5 (2) |
O2—C1—O1 | 123.5 (3) | O10—C21—H21A | 110.4 |
O2—C1—C2 | 119.4 (3) | C20—C21—H21A | 110.4 |
O1—C1—C2 | 117.1 (3) | O10—C21—H21B | 110.4 |
C3B—C2—C7B | 118.7 (3) | C20—C21—H21B | 110.4 |
C3A—C2—C7A | 118.7 (3) | H21A—C21—H21B | 108.6 |
C3B—C2—C1 | 120.7 (3) | O10—C22—C23 | 125.0 (3) |
C3A—C2—C1 | 120.7 (3) | O10—C22—C27 | 114.0 (2) |
C7B—C2—C1 | 120.5 (3) | C23—C22—C27 | 121.0 (3) |
C7A—C2—C1 | 120.5 (3) | C22—C23—C24 | 119.3 (3) |
C5B—C6—C7B | 119.1 (3) | C22—C23—H23 | 120.4 |
C5A—C6—C7A | 119.1 (3) | C24—C23—H23 | 120.4 |
C5A—C6—H6A | 120.5 | C25—C24—C23 | 121.8 (3) |
C7A—C6—H6A | 120.5 | C25—C24—H24 | 119.1 |
C5B—C6—H6B | 120.5 | C23—C24—H24 | 119.1 |
C7B—C6—H6B | 120.5 | C24—C25—C26 | 119.7 (3) |
O8—C8—H8A | 109.5 | C24—C25—H25 | 120.2 |
O8—C8—H8B | 109.5 | C26—C25—H25 | 120.2 |
H8A—C8—H8B | 109.5 | C31—C26—C27 | 118.7 (3) |
O8—C8—H8C | 109.5 | C31—C26—C25 | 122.0 (3) |
H8A—C8—H8C | 109.5 | C27—C26—C25 | 119.2 (3) |
H8B—C8—H8C | 109.5 | C26—C27—C28 | 119.3 (3) |
O8—C9—C10 | 124.6 (2) | C26—C27—C22 | 118.8 (3) |
O8—C9—C14 | 115.3 (2) | C28—C27—C22 | 121.9 (3) |
C10—C9—C14 | 120.2 (3) | C29—C28—C27 | 120.7 (3) |
C9—C10—C11 | 120.7 (3) | C29—C28—H28 | 119.7 |
C9—C10—H10 | 119.7 | C27—C28—H28 | 119.7 |
C11—C10—H10 | 119.7 | C28—C29—C30 | 120.0 (3) |
C12—C11—C10 | 120.1 (3) | C28—C29—H29 | 120.0 |
C12—C11—H11 | 119.9 | C30—C29—H29 | 120.0 |
C10—C11—H11 | 119.9 | C31—C30—C29 | 120.3 (3) |
C11—C12—C13 | 119.4 (3) | C31—C30—H30 | 119.9 |
C11—C12—H12 | 120.3 | C29—C30—H30 | 119.9 |
C13—C12—H12 | 120.3 | C30—C31—C26 | 121.0 (3) |
C14—C13—C12 | 121.8 (3) | C30—C31—H31 | 119.5 |
C14—C13—H13 | 119.1 | C26—C31—H31 | 119.5 |
C12—C13—H13 | 119.1 | C14—N1—C18 | 115.6 (2) |
C13—C14—C9 | 117.8 (3) | C14—N1—C15 | 114.6 (2) |
C13—C14—N1 | 123.3 (2) | C18—N1—C15 | 108.4 (2) |
C9—C14—N1 | 118.9 (2) | C16—N2—C19 | 112.1 (2) |
N1—C15—C16 | 110.0 (2) | C16—N2—C17 | 110.9 (2) |
N1—C15—H15A | 109.7 | C19—N2—C17 | 109.1 (2) |
C16—C15—H15A | 109.7 | C16—N2—H2 | 108.2 |
N1—C15—H15B | 109.7 | C19—N2—H2 | 108.2 |
C16—C15—H15B | 109.7 | C17—N2—H2 | 108.2 |
H15A—C15—H15B | 108.2 | C9—O8—C8 | 116.5 (2) |
N2—C16—C15 | 111.8 (2) | C20—O9—H9 | 109.5 |
N2—C16—H16A | 109.3 | C22—O10—C21 | 119.2 (2) |
C15—C16—H16A | 109.3 |
C24H29N2O3·C7H5O5 | F(000) = 1192 |
Mr = 562.60 | Dx = 1.349 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.074 (2) Å | Cell parameters from 9984 reflections |
b = 17.895 (3) Å | θ = 2.6–30.4° |
c = 14.000 (2) Å | µ = 0.10 mm−1 |
β = 92.859 (8)° | T = 293 K |
V = 2770.9 (8) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.15 × 0.1 mm |
Bruker APEX-II CCD diffractometer | 6782 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.066 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0895 before and 0.0582 after correction. The Ratio of minimum to maximum transmission is 0.9491. The λ/2 correction factor is Not present. | θmax = 30.5°, θmin = 1.8° |
Tmin = 0.708, Tmax = 0.746 | h = −15→15 |
104029 measured reflections | k = −25→25 |
8405 independent reflections | l = −19→19 |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.0714P)2 + 0.8514P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
8405 reflections | Δρmax = 0.41 e Å−3 |
375 parameters | Δρmin = −0.48 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.27802 (8) | 0.24793 (5) | 0.33918 (7) | 0.0219 (2) | |
O2 | −0.31263 (8) | 0.55488 (5) | 0.45801 (7) | 0.02157 (19) | |
O3 | 0.03102 (8) | 0.22374 (5) | 0.34668 (7) | 0.02041 (19) | |
H3 | 0.067747 | 0.207793 | 0.402769 | 0.031* | |
N1 | −0.18402 (9) | 0.44874 (6) | 0.55140 (7) | 0.0169 (2) | |
N2 | −0.01220 (9) | 0.34896 (6) | 0.47050 (7) | 0.0168 (2) | |
H2 | −0.034338 | 0.300791 | 0.492330 | 0.020* | |
C1 | −0.47045 (12) | 0.55668 (8) | 0.68470 (11) | 0.0260 (3) | |
H1 | −0.534081 | 0.580539 | 0.713107 | 0.031* | |
C2 | −0.44284 (12) | 0.57543 (7) | 0.59175 (10) | 0.0225 (3) | |
H2A | −0.487118 | 0.612263 | 0.558823 | 0.027* | |
C3 | −0.34890 (11) | 0.53907 (7) | 0.54792 (9) | 0.0180 (2) | |
C4 | −0.28141 (11) | 0.48325 (7) | 0.59804 (9) | 0.0179 (2) | |
C5 | −0.22299 (11) | 0.39869 (7) | 0.47278 (9) | 0.0189 (2) | |
H5A | −0.286906 | 0.422301 | 0.433660 | 0.023* | |
H5B | −0.254628 | 0.352757 | 0.498526 | 0.023* | |
C6 | −0.11679 (11) | 0.38108 (7) | 0.41187 (9) | 0.0184 (2) | |
H6A | −0.142297 | 0.345707 | 0.362393 | 0.022* | |
H6B | −0.091104 | 0.426452 | 0.380854 | 0.022* | |
C7 | 0.09880 (11) | 0.34215 (7) | 0.41431 (9) | 0.0194 (2) | |
H7A | 0.162946 | 0.319974 | 0.454639 | 0.023* | |
H7B | 0.124957 | 0.391753 | 0.396511 | 0.023* | |
C8 | 0.07965 (11) | 0.29521 (7) | 0.32435 (9) | 0.0186 (2) | |
H8 | 0.021410 | 0.321020 | 0.280890 | 0.022* | |
C9 | 0.19887 (12) | 0.28859 (7) | 0.27514 (9) | 0.0206 (2) | |
H9A | 0.187235 | 0.262231 | 0.214839 | 0.025* | |
H9B | 0.231709 | 0.337706 | 0.262827 | 0.025* | |
C10 | 0.39538 (11) | 0.23690 (7) | 0.31477 (10) | 0.0197 (2) | |
C11 | 0.46447 (12) | 0.19090 (7) | 0.38046 (10) | 0.0220 (3) | |
C12 | 0.41171 (13) | 0.15386 (8) | 0.45735 (10) | 0.0266 (3) | |
H12 | 0.330295 | 0.160990 | 0.468010 | 0.032* | |
C13 | 0.48038 (16) | 0.10734 (10) | 0.51636 (11) | 0.0345 (3) | |
H13 | 0.444735 | 0.082180 | 0.565803 | 0.041* | |
C14 | 0.60509 (16) | 0.09757 (10) | 0.50221 (13) | 0.0394 (4) | |
H14 | 0.651015 | 0.066007 | 0.542349 | 0.047* | |
C15 | −0.37532 (13) | 0.61327 (8) | 0.40558 (11) | 0.0273 (3) | |
H15A | −0.369396 | 0.658946 | 0.441461 | 0.041* | |
H15B | −0.458863 | 0.599825 | 0.395126 | 0.041* | |
H15C | −0.339631 | 0.620064 | 0.345086 | 0.041* | |
C16 | 0.44463 (13) | 0.26718 (7) | 0.23561 (11) | 0.0252 (3) | |
H16 | 0.396691 | 0.293996 | 0.191250 | 0.030* | |
C17 | 0.56958 (15) | 0.25705 (9) | 0.22232 (13) | 0.0341 (4) | |
H17 | 0.603665 | 0.277936 | 0.169117 | 0.041* | |
C18 | 0.64067 (14) | 0.21719 (9) | 0.28623 (14) | 0.0368 (4) | |
H18 | 0.723181 | 0.213297 | 0.277720 | 0.044* | |
C19 | 0.59009 (13) | 0.18143 (8) | 0.36590 (12) | 0.0290 (3) | |
C20 | 0.65808 (14) | 0.13424 (10) | 0.42997 (14) | 0.0380 (4) | |
H20 | 0.740484 | 0.128252 | 0.422475 | 0.046* | |
C21 | 0.01785 (11) | 0.39593 (7) | 0.55749 (9) | 0.0197 (2) | |
H21A | 0.051990 | 0.443102 | 0.537935 | 0.024* | |
H21B | 0.078108 | 0.370435 | 0.598242 | 0.024* | |
C22 | −0.09336 (12) | 0.41075 (7) | 0.61337 (9) | 0.0202 (2) | |
H22A | −0.125779 | 0.363935 | 0.635837 | 0.024* | |
H22B | −0.072075 | 0.441686 | 0.668560 | 0.024* | |
C23 | −0.30959 (13) | 0.46663 (8) | 0.69170 (9) | 0.0228 (3) | |
H23 | −0.264680 | 0.430752 | 0.725898 | 0.027* | |
C24 | −0.40436 (14) | 0.50309 (8) | 0.73499 (10) | 0.0275 (3) | |
H24 | −0.422635 | 0.491231 | 0.797309 | 0.033* | |
O4 | 0.86113 (9) | 0.60252 (5) | 0.23110 (7) | 0.0228 (2) | |
H4 | 0.908056 | 0.642454 | 0.211948 | 0.034* | |
O5 | 0.94551 (10) | 0.27750 (5) | 0.06850 (7) | 0.0259 (2) | |
O6 | 1.15595 (9) | 0.47049 (6) | 0.06171 (7) | 0.0238 (2) | |
H6 | 1.164665 | 0.422120 | 0.033484 | 0.036* | |
O7 | 0.80402 (9) | 0.34662 (5) | 0.17428 (7) | 0.0250 (2) | |
O8 | 1.10932 (9) | 0.33318 (6) | 0.01555 (7) | 0.0246 (2) | |
C25 | 0.90282 (12) | 0.53886 (7) | 0.19120 (8) | 0.0179 (2) | |
C26 | 1.01181 (11) | 0.53700 (7) | 0.14503 (9) | 0.0189 (2) | |
H26 | 1.058419 | 0.579999 | 0.140831 | 0.023* | |
C27 | 1.05000 (11) | 0.47021 (7) | 0.10537 (9) | 0.0175 (2) | |
C28 | 0.98008 (11) | 0.40414 (7) | 0.11149 (8) | 0.0171 (2) | |
C29 | 1.01430 (12) | 0.33462 (7) | 0.06299 (9) | 0.0198 (2) | |
C30 | 0.87211 (11) | 0.40832 (7) | 0.16157 (9) | 0.0182 (2) | |
C31 | 0.83320 (11) | 0.47485 (7) | 0.20064 (9) | 0.0191 (2) | |
H31 | 0.761657 | 0.476598 | 0.232654 | 0.023* | |
H7 | 0.840 (2) | 0.3099 (12) | 0.1342 (17) | 0.064 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0162 (4) | 0.0254 (5) | 0.0243 (4) | 0.0040 (3) | 0.0037 (3) | 0.0060 (4) |
O2 | 0.0194 (4) | 0.0213 (4) | 0.0239 (5) | 0.0043 (3) | −0.0001 (3) | 0.0058 (3) |
O3 | 0.0223 (4) | 0.0160 (4) | 0.0231 (4) | −0.0010 (3) | 0.0026 (3) | 0.0006 (3) |
N1 | 0.0162 (5) | 0.0172 (5) | 0.0171 (5) | 0.0033 (4) | −0.0025 (4) | −0.0019 (4) |
N2 | 0.0171 (5) | 0.0131 (4) | 0.0200 (5) | 0.0017 (3) | −0.0009 (4) | −0.0003 (4) |
C1 | 0.0198 (6) | 0.0249 (6) | 0.0335 (7) | −0.0001 (5) | 0.0036 (5) | −0.0110 (5) |
C2 | 0.0162 (6) | 0.0166 (5) | 0.0346 (7) | 0.0015 (4) | −0.0011 (5) | −0.0053 (5) |
C3 | 0.0156 (5) | 0.0161 (5) | 0.0220 (6) | −0.0015 (4) | −0.0023 (4) | −0.0020 (4) |
C4 | 0.0169 (5) | 0.0156 (5) | 0.0210 (6) | 0.0006 (4) | −0.0012 (4) | −0.0030 (4) |
C5 | 0.0176 (5) | 0.0192 (5) | 0.0196 (5) | 0.0010 (4) | −0.0029 (4) | −0.0034 (4) |
C6 | 0.0183 (5) | 0.0189 (5) | 0.0177 (5) | 0.0033 (4) | −0.0028 (4) | −0.0008 (4) |
C7 | 0.0160 (5) | 0.0177 (5) | 0.0244 (6) | 0.0004 (4) | 0.0005 (4) | −0.0009 (4) |
C8 | 0.0180 (5) | 0.0156 (5) | 0.0220 (6) | 0.0022 (4) | 0.0000 (4) | 0.0015 (4) |
C9 | 0.0216 (6) | 0.0184 (5) | 0.0218 (6) | 0.0022 (5) | 0.0025 (5) | 0.0038 (4) |
C10 | 0.0167 (5) | 0.0165 (5) | 0.0263 (6) | −0.0009 (4) | 0.0039 (5) | −0.0036 (4) |
C11 | 0.0190 (6) | 0.0195 (6) | 0.0272 (6) | 0.0012 (4) | 0.0000 (5) | −0.0065 (5) |
C12 | 0.0238 (6) | 0.0300 (7) | 0.0259 (7) | 0.0058 (5) | −0.0006 (5) | 0.0007 (5) |
C13 | 0.0369 (8) | 0.0373 (8) | 0.0287 (7) | 0.0097 (7) | −0.0053 (6) | 0.0023 (6) |
C14 | 0.0357 (9) | 0.0403 (9) | 0.0405 (9) | 0.0155 (7) | −0.0155 (7) | −0.0073 (7) |
C15 | 0.0258 (7) | 0.0230 (6) | 0.0324 (7) | 0.0050 (5) | −0.0059 (5) | 0.0069 (5) |
C16 | 0.0259 (7) | 0.0182 (6) | 0.0322 (7) | −0.0023 (5) | 0.0093 (5) | −0.0020 (5) |
C17 | 0.0296 (8) | 0.0264 (7) | 0.0480 (9) | −0.0039 (6) | 0.0192 (7) | −0.0029 (6) |
C18 | 0.0195 (7) | 0.0323 (8) | 0.0597 (11) | −0.0008 (6) | 0.0141 (7) | −0.0072 (7) |
C19 | 0.0189 (6) | 0.0257 (7) | 0.0424 (8) | 0.0021 (5) | 0.0003 (6) | −0.0106 (6) |
C20 | 0.0219 (7) | 0.0382 (9) | 0.0531 (10) | 0.0094 (6) | −0.0061 (7) | −0.0113 (8) |
C21 | 0.0184 (6) | 0.0179 (5) | 0.0221 (6) | 0.0034 (4) | −0.0046 (4) | −0.0031 (4) |
C22 | 0.0208 (6) | 0.0203 (6) | 0.0191 (6) | 0.0044 (4) | −0.0034 (4) | −0.0008 (4) |
C23 | 0.0245 (6) | 0.0237 (6) | 0.0199 (6) | 0.0022 (5) | −0.0001 (5) | −0.0016 (5) |
C24 | 0.0293 (7) | 0.0297 (7) | 0.0240 (6) | 0.0000 (6) | 0.0054 (5) | −0.0072 (5) |
O4 | 0.0277 (5) | 0.0187 (4) | 0.0226 (4) | 0.0017 (4) | 0.0058 (4) | −0.0010 (3) |
O5 | 0.0329 (5) | 0.0171 (4) | 0.0280 (5) | −0.0045 (4) | 0.0046 (4) | −0.0040 (4) |
O6 | 0.0187 (4) | 0.0250 (5) | 0.0282 (5) | −0.0042 (4) | 0.0059 (4) | −0.0048 (4) |
O7 | 0.0270 (5) | 0.0202 (4) | 0.0284 (5) | −0.0085 (4) | 0.0060 (4) | −0.0003 (4) |
O8 | 0.0241 (5) | 0.0241 (5) | 0.0258 (5) | 0.0016 (4) | 0.0037 (4) | −0.0046 (4) |
C25 | 0.0207 (6) | 0.0178 (5) | 0.0151 (5) | 0.0014 (4) | −0.0001 (4) | 0.0007 (4) |
C26 | 0.0195 (6) | 0.0176 (5) | 0.0195 (5) | −0.0043 (4) | 0.0004 (4) | −0.0010 (4) |
C27 | 0.0164 (5) | 0.0200 (5) | 0.0159 (5) | −0.0017 (4) | −0.0004 (4) | 0.0004 (4) |
C28 | 0.0186 (5) | 0.0167 (5) | 0.0157 (5) | −0.0008 (4) | −0.0007 (4) | 0.0001 (4) |
C29 | 0.0236 (6) | 0.0184 (5) | 0.0170 (5) | 0.0003 (4) | −0.0015 (5) | −0.0006 (4) |
C30 | 0.0192 (5) | 0.0193 (6) | 0.0158 (5) | −0.0039 (4) | −0.0016 (4) | 0.0030 (4) |
C31 | 0.0180 (5) | 0.0215 (6) | 0.0179 (5) | −0.0008 (4) | 0.0026 (4) | 0.0012 (4) |
O1—C9 | 1.4223 (16) | C13—C14 | 1.416 (2) |
O1—C10 | 1.3744 (15) | C14—H14 | 0.9300 |
O2—C3 | 1.3697 (16) | C14—C20 | 1.363 (3) |
O2—C15 | 1.4358 (16) | C15—H15A | 0.9600 |
O3—H3 | 0.9120 | C15—H15B | 0.9600 |
O3—C8 | 1.4283 (15) | C15—H15C | 0.9600 |
N1—C4 | 1.4288 (15) | C16—H16 | 0.9300 |
N1—C5 | 1.4670 (16) | C16—C17 | 1.417 (2) |
N1—C22 | 1.4615 (16) | C17—H17 | 0.9300 |
N2—H2 | 0.9508 | C17—C18 | 1.363 (3) |
N2—C6 | 1.5002 (16) | C18—H18 | 0.9300 |
N2—C7 | 1.4971 (16) | C18—C19 | 1.425 (2) |
N2—C21 | 1.5032 (16) | C19—C20 | 1.420 (2) |
C1—H1 | 0.9300 | C20—H20 | 0.9300 |
C1—C2 | 1.393 (2) | C21—H21A | 0.9700 |
C1—C24 | 1.378 (2) | C21—H21B | 0.9700 |
C2—H2A | 0.9300 | C21—C22 | 1.5150 (18) |
C2—C3 | 1.3949 (17) | C22—H22A | 0.9700 |
C3—C4 | 1.4128 (17) | C22—H22B | 0.9700 |
C4—C23 | 1.3950 (18) | C23—H23 | 0.9300 |
C5—H5A | 0.9700 | C23—C24 | 1.3992 (19) |
C5—H5B | 0.9700 | C24—H24 | 0.9300 |
C5—C6 | 1.5198 (17) | O4—H4 | 0.9308 |
C6—H6A | 0.9700 | O4—C25 | 1.3597 (15) |
C6—H6B | 0.9700 | O5—C29 | 1.2794 (16) |
C7—H7A | 0.9700 | O6—H6 | 0.9584 |
C7—H7B | 0.9700 | O6—C27 | 1.3496 (15) |
C7—C8 | 1.5200 (18) | O7—C30 | 1.3537 (15) |
C8—H8 | 0.9800 | O7—H7 | 0.962 (16) |
C8—C9 | 1.5239 (18) | O8—C29 | 1.2722 (16) |
C9—H9A | 0.9700 | C25—C26 | 1.3977 (17) |
C9—H9B | 0.9700 | C25—C31 | 1.3909 (18) |
C10—C11 | 1.4277 (19) | C26—H26 | 0.9300 |
C10—C16 | 1.3710 (19) | C26—C27 | 1.3926 (17) |
C11—C12 | 1.415 (2) | C27—C28 | 1.4182 (17) |
C11—C19 | 1.4261 (19) | C28—C29 | 1.4759 (17) |
C12—H12 | 0.9300 | C28—C30 | 1.4179 (17) |
C12—C13 | 1.375 (2) | C30—C31 | 1.3877 (18) |
C13—H13 | 0.9300 | C31—H31 | 0.9300 |
C10—O1—C9 | 118.52 (10) | C13—C14—H14 | 119.9 |
C3—O2—C15 | 117.62 (10) | C20—C14—C13 | 120.23 (15) |
C8—O3—H3 | 108.2 | C20—C14—H14 | 119.9 |
C4—N1—C5 | 113.97 (10) | O2—C15—H15A | 109.5 |
C4—N1—C22 | 116.21 (10) | O2—C15—H15B | 109.5 |
C22—N1—C5 | 109.21 (10) | O2—C15—H15C | 109.5 |
C6—N2—H2 | 108.6 | H15A—C15—H15B | 109.5 |
C6—N2—C21 | 111.27 (9) | H15A—C15—H15C | 109.5 |
C7—N2—H2 | 109.1 | H15B—C15—H15C | 109.5 |
C7—N2—C6 | 112.05 (10) | C10—C16—H16 | 120.5 |
C7—N2—C21 | 108.47 (10) | C10—C16—C17 | 119.08 (15) |
C21—N2—H2 | 107.3 | C17—C16—H16 | 120.5 |
C2—C1—H1 | 119.7 | C16—C17—H17 | 119.5 |
C24—C1—H1 | 119.7 | C18—C17—C16 | 121.09 (15) |
C24—C1—C2 | 120.61 (12) | C18—C17—H17 | 119.5 |
C1—C2—H2A | 119.9 | C17—C18—H18 | 119.6 |
C1—C2—C3 | 120.14 (13) | C17—C18—C19 | 120.81 (14) |
C3—C2—H2A | 119.9 | C19—C18—H18 | 119.6 |
O2—C3—C2 | 124.55 (12) | C18—C19—C11 | 118.87 (14) |
O2—C3—C4 | 115.49 (11) | C20—C19—C11 | 118.07 (15) |
C2—C3—C4 | 119.93 (12) | C20—C19—C18 | 123.02 (14) |
C3—C4—N1 | 118.12 (11) | C14—C20—C19 | 121.39 (15) |
C23—C4—N1 | 123.14 (11) | C14—C20—H20 | 119.3 |
C23—C4—C3 | 118.69 (11) | C19—C20—H20 | 119.3 |
N1—C5—H5A | 109.7 | N2—C21—H21A | 109.4 |
N1—C5—H5B | 109.7 | N2—C21—H21B | 109.4 |
N1—C5—C6 | 109.91 (10) | N2—C21—C22 | 111.31 (10) |
H5A—C5—H5B | 108.2 | H21A—C21—H21B | 108.0 |
C6—C5—H5A | 109.7 | C22—C21—H21A | 109.4 |
C6—C5—H5B | 109.7 | C22—C21—H21B | 109.4 |
N2—C6—C5 | 111.74 (10) | N1—C22—C21 | 109.08 (10) |
N2—C6—H6A | 109.3 | N1—C22—H22A | 109.9 |
N2—C6—H6B | 109.3 | N1—C22—H22B | 109.9 |
C5—C6—H6A | 109.3 | C21—C22—H22A | 109.9 |
C5—C6—H6B | 109.3 | C21—C22—H22B | 109.9 |
H6A—C6—H6B | 107.9 | H22A—C22—H22B | 108.3 |
N2—C7—H7A | 108.9 | C4—C23—H23 | 119.5 |
N2—C7—H7B | 108.9 | C4—C23—C24 | 121.02 (13) |
N2—C7—C8 | 113.34 (10) | C24—C23—H23 | 119.5 |
H7A—C7—H7B | 107.7 | C1—C24—C23 | 119.60 (13) |
C8—C7—H7A | 108.9 | C1—C24—H24 | 120.2 |
C8—C7—H7B | 108.9 | C23—C24—H24 | 120.2 |
O3—C8—C7 | 110.61 (10) | C25—O4—H4 | 108.6 |
O3—C8—H8 | 108.3 | C27—O6—H6 | 106.9 |
O3—C8—C9 | 111.96 (10) | C30—O7—H7 | 103.5 (15) |
C7—C8—H8 | 108.3 | O4—C25—C26 | 121.92 (11) |
C7—C8—C9 | 109.23 (11) | O4—C25—C31 | 116.73 (11) |
C9—C8—H8 | 108.3 | C31—C25—C26 | 121.33 (11) |
O1—C9—C8 | 105.99 (10) | C25—C26—H26 | 120.3 |
O1—C9—H9A | 110.5 | C27—C26—C25 | 119.43 (11) |
O1—C9—H9B | 110.5 | C27—C26—H26 | 120.3 |
C8—C9—H9A | 110.5 | O6—C27—C26 | 117.74 (11) |
C8—C9—H9B | 110.5 | O6—C27—C28 | 121.34 (11) |
H9A—C9—H9B | 108.7 | C26—C27—C28 | 120.92 (11) |
O1—C10—C11 | 113.94 (11) | C27—C28—C29 | 121.43 (11) |
C16—C10—O1 | 124.29 (12) | C30—C28—C27 | 117.54 (11) |
C16—C10—C11 | 121.77 (12) | C30—C28—C29 | 120.94 (11) |
C12—C11—C10 | 122.12 (12) | O5—C29—C28 | 118.58 (11) |
C12—C11—C19 | 119.72 (13) | O8—C29—O5 | 121.73 (12) |
C19—C11—C10 | 118.15 (13) | O8—C29—C28 | 119.68 (11) |
C11—C12—H12 | 119.9 | O7—C30—C28 | 120.73 (11) |
C13—C12—C11 | 120.24 (14) | O7—C30—C31 | 117.51 (11) |
C13—C12—H12 | 119.9 | C31—C30—C28 | 121.75 (11) |
C12—C13—H13 | 119.8 | C25—C31—H31 | 120.5 |
C12—C13—C14 | 120.31 (16) | C30—C31—C25 | 118.99 (11) |
C14—C13—H13 | 119.8 | C30—C31—H31 | 120.5 |
O1—C10—C11—C12 | 6.60 (18) | C12—C11—C19—C20 | 0.2 (2) |
O1—C10—C11—C19 | −174.68 (11) | C12—C13—C14—C20 | 0.0 (3) |
O1—C10—C16—C17 | 174.63 (13) | C13—C14—C20—C19 | −1.6 (3) |
O2—C3—C4—N1 | −0.35 (16) | C15—O2—C3—C2 | 0.38 (18) |
O2—C3—C4—C23 | 177.07 (11) | C15—O2—C3—C4 | −177.62 (11) |
O3—C8—C9—O1 | −58.06 (13) | C16—C10—C11—C12 | −174.05 (13) |
N1—C4—C23—C24 | 178.65 (12) | C16—C10—C11—C19 | 4.68 (19) |
N1—C5—C6—N2 | 55.64 (13) | C16—C17—C18—C19 | 3.1 (2) |
N2—C7—C8—O3 | −53.59 (13) | C17—C18—C19—C11 | −3.0 (2) |
N2—C7—C8—C9 | −177.26 (10) | C17—C18—C19—C20 | 174.62 (16) |
N2—C21—C22—N1 | −58.70 (13) | C18—C19—C20—C14 | −176.20 (16) |
C1—C2—C3—O2 | −178.09 (12) | C19—C11—C12—C13 | −1.7 (2) |
C1—C2—C3—C4 | −0.18 (19) | C21—N2—C6—C5 | −49.81 (13) |
C2—C1—C24—C23 | −0.8 (2) | C21—N2—C7—C8 | 179.68 (10) |
C2—C3—C4—N1 | −178.45 (11) | C22—N1—C4—C3 | 160.56 (11) |
C2—C3—C4—C23 | −1.03 (18) | C22—N1—C4—C23 | −16.73 (17) |
C3—C4—C23—C24 | 1.4 (2) | C22—N1—C5—C6 | −62.98 (13) |
C4—N1—C5—C6 | 165.20 (10) | C24—C1—C2—C3 | 1.1 (2) |
C4—N1—C22—C21 | −164.98 (10) | O4—C25—C26—C27 | −179.94 (11) |
C4—C23—C24—C1 | −0.5 (2) | O4—C25—C31—C30 | −179.69 (11) |
C5—N1—C4—C3 | −71.10 (14) | O6—C27—C28—C29 | −5.62 (18) |
C5—N1—C4—C23 | 111.60 (14) | O6—C27—C28—C30 | 177.81 (11) |
C5—N1—C22—C21 | 64.40 (13) | O7—C30—C31—C25 | 178.24 (11) |
C6—N2—C7—C8 | −57.10 (13) | C25—C26—C27—O6 | −179.73 (11) |
C6—N2—C21—C22 | 51.40 (13) | C25—C26—C27—C28 | −0.21 (19) |
C7—N2—C6—C5 | −171.44 (10) | C26—C25—C31—C30 | −1.31 (19) |
C7—N2—C21—C22 | 175.09 (10) | C26—C27—C28—C29 | 174.88 (11) |
C7—C8—C9—O1 | 64.81 (13) | C26—C27—C28—C30 | −1.69 (18) |
C9—O1—C10—C11 | −175.67 (11) | C27—C28—C29—O5 | −177.73 (12) |
C9—O1—C10—C16 | 5.00 (18) | C27—C28—C29—O8 | 0.94 (18) |
C10—O1—C9—C8 | −176.73 (10) | C27—C28—C30—O7 | −176.74 (11) |
C10—C11—C12—C13 | 177.00 (14) | C27—C28—C30—C31 | 2.17 (18) |
C10—C11—C19—C18 | −0.8 (2) | C28—C30—C31—C25 | −0.71 (19) |
C10—C11—C19—C20 | −178.54 (13) | C29—C28—C30—O7 | 6.67 (18) |
C10—C16—C17—C18 | 0.7 (2) | C29—C28—C30—C31 | −174.42 (12) |
C11—C10—C16—C17 | −4.7 (2) | C30—C28—C29—O5 | −1.28 (18) |
C11—C12—C13—C14 | 1.6 (2) | C30—C28—C29—O8 | 177.39 (12) |
C11—C19—C20—C14 | 1.4 (2) | C31—C25—C26—C27 | 1.77 (19) |
C12—C11—C19—C18 | 177.93 (14) |
Funding information
R. B. Dandela thanks DST-SERB for a Ramanujan fellowship (SB/S2/RJN-075/2016) and S. Tothadi thanks DST-SERB for an NPDF Fellowship (PDF/2017/000047). A. Nangia thanks CSIR-NCL and DST-SERB (JC Bose fellowship, SR/S2/JCB-06/2009 and Multi-component cocrystals, EMR/2015/002075) and CSIR (Pharmaceutical Cocrystals, 02 (0223)/15/EMR-II) for funding. Financial and infrastructure support from the University Grants Commission (through UPE and CAS programs) and the Department of Science and Technology (through PURSE and FIST programs) is gratefully acknowledged.
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