Systematic synthesis of a 6-component organic-salt alloy of naftopidil, and pentanary, quaternary and ternary multicomponent crystals

Dandela, R.; Tothadi, S.; Marelli, U.K.; Nangia, A.

doi:10.1107/S2052252518014057

research papers

IUCrJ

Volume 5| Part 6| November 2018| Pages 816-822

ISSN: 2052-2525

https://doi.org/10.1107/S2052252518014057

CHEMISTRY | CRYSTENG

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Systematic synthesis of a 6-component organic-salt alloy of naftopidil, and pentanary, quaternary and ternary multicomponent crystals

Rambabu Dandela,^a ^*‡ Srinu Tothadi,^a § Udaya Kiran Marelli ^a,^b and Ashwini Nangia ^a,^c ^*

^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

Edited by M. Eddaoudi, King Abdullah University, Saudi Arabia (Received 25 May 2018; accepted 3 October 2018; online 24 October 2018)

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 carboxylic acids (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 [R_2^2] (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 carboxylic acids in the crystal structure 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 differential scanning calorimetry techniques.

Keywords: active pharmaceutical ingredients; crystal engineering; naftopidil; multicomponent solids; 6-component crystals; organic-salt alloys.

CCDC references: 1817125; 1817126; 1817127; 1817128; 1817129; 1817130; 1817146; 1817147; 1817148; 1817149; 1817150; 1817151; 1817158; 1817159; 1817160; 1817161; 1817163; 1817164; 1817165; 1817166; 1817167; 1817168; 1817169; 1817170; 1840048; 1874903

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 solid solution. They upgraded the initial 4-component synthetic dead-end cocrystal to a 6-component solid solution 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 crystal structure refinement 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 [R_2^2] (9) supramolecular synthon. An additional six alloys were characterized by powder X-ray diffraction (PXRD), NMR and differential scanning calorimetry (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 $[Agilent (2010). CrysAlisPro. Oxford Diffraction Ltd: Abingdon, UK.]$ ). 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 direct methods 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 refinement 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.

Table 1
Structural data for the binary salts of naftopidil

Binary salt	Space group	a (Å)	b (Å)	c (Å)	β (°)	V (Å³)
(12)	P2₁/c	11.0695 (2)	17.7360 (3)	13.5179 (3)	97.3794 (19)	2631.97
(13)	P2₁/c	11.2350 (5)	17.6516 (6)	13.4798 (6)	96.269 (4)	2657.27
(14)	P2₁/c	11.3258 (4)	17.8349 (7)	13.4077 (7)	95.800 (4)	2694.42
(15)	P2₁/c	10.843 (4)	17.862 (6)	13.913 (6)	91.715 (12)	2693.43
(16)	P2₁	11.4733 (3)	17.6286 (5)	13.6530 (4)	93.290 (2)	2756.88

Refinement of organic-salt alloy crystal data: first, all non-hydrogen atoms were refined isotropically followed by anisotropic refinement. Substituted oxygen atoms of the acids (coformers) showed unusual ellipsoid electron density caused by multiple atoms in the envelope; free refinement 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 refinement 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 chemical shift 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.

2.5. Cambridge Structural Database analysis

The [R_2^2] (9) synthon was drawn using ConQest and the intermolecular distance was taken as the distance within the sum of the van der Waals radii + 0.0 Å.

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 [R_2^2] (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 [R_2^2] (9) motif [Fig. 1(b), Table S4]. The recurrence of the [R_2^2] (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 [R_2^2] (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 [R_2^2] (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 crystal structure 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 space group 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 space group, 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 refinement 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 crystal structure (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 [R_2^2] (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 [R_2^2] (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.

Table 2
Salt and salt-alloy synthesis: naftopidil (1) with five aromatic acids

Crystallographic information for the organic salts and salt alloys is given in Table S2.

Naftopidil	Coformer	Binary†	Hexanary‡	Pentanary§	Quaternary¶	Ternary††
(1)	(2)	(12)	(123456)	(12356)‡‡	(1234)	(123)‡‡
	(3)	(13)		(12346)‡‡	(1235)	(124)
		(14)		(12345)‡‡	(1236)	(125)§§
	(4)	(15)		(13456)‡‡§§	(1245)	(126)
		(16)		(12456)‡‡§§	(1246)	(134)
	(5)				(1256)§§	(135)
					(1345)§§	(136)
	(6)				(1346)	(145)
					(1356)	(146)
					(1456)‡‡	(156)§§

†Binary salt: 1 mmol of (1) and 1 mmol of each acid.
‡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.

Figure 1
(a) Naftopidil (1) and coformers benzoic acid (2), 2-hydroxybenzoic acid, (3) 2,3-dihydroxybenzoic acid (4), 2,4-dihydroxybenzoic acid (5) and 2,6-dihydroxybenzoic acid (6) used for cocrystallization; and (b) the ionic synthon of the [R_2^2]

(9) graph set that is observed in all single-crystal structures (salts). In the synthon, complete proton transfer produces an N⁺—H⋯O⁻ and O—H⋯O hydrogen-bonded cyclic motif.

Figure 2
Binary salts of naftopidil (1) with coformers (2)–(6): (a) (12), (b) (13), (c) (14), (d) (15) and (e) (16).

Figure 3
Synthesis of multicomponent organic-salt alloys: the first five binary salts [(12), (13), (14), (15) and (16)] were synthesized and their structures analyzed. All binary salts are isostructural. Similarly ternary, quaternary and pentanary crystal alloys were crystallized. Cocrystallization of naftopidil (1) (1.0 mmol) with benzoic acid (2), salicylic acid (3), 2,3-dihydroxybenzoic acid (4), 2,4-dihydroxybenzoic acid (5) and 2,6-dihydroxybenzoic acid (6) (0.2 mmol of each coformer) resulted in a 6-component organic-salt alloy (hexanary alloy).

Figure 4
Hexacomponent (123456) alloy: (a) single crystal, (b) single-crystal structure showing one full molecule of naftopidil (1) and five acids with a site occupancy factor of 0.12 benzoic acid (2), 0.27 2-hydroxybenzoic acid (3), 0.14 2,3-dihydroxybenzoic acid (4), 0.20 2,4-dihydroxybenzoic acid (5) and 0.27 2,6-dihydroxybenzoic acid (6). The binary salts form an [R_2^2]

(9) synthon which is also present in the hexacomponent (123456) alloy. (c) DSC endotherm, showing a single melting point at 176°C which is different from the melting point of the single components as well as the binary salts. (d) PXRD shows bulk-phase purity experimental PXRD pattern compared with the calculated powder diffraction line pattern from the crystal structure.

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 [R_2^2] (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 crystal structure 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 ).

Figure 5
(a) Ternary (134) (b) quaternary (1346) and (c) pentanary (12346) organic-salt alloys. In the ternary (134) alloy, 2-hydroxybenzoic acid and 2,3-dihydroxybenzoic acid occupy the same site but with a variable occupancy of 0.49 and 0.51. Similarly, in the quaternary (1346) alloy the site occupancy of 2-hydroxybenzoic acid, 2,3-dihydroxybenzoic acid and 2,6-dihydroxybenzoic acid is 0.19, 0.43 and 0.38, respectively. Likewise, in pentanary (12346) alloy, the site occupancy of benzoic acid, 2-hydroxybenzoic acid, 2,3-dihydroxybenzoic acid and 2,6-dihydroxybenzoic acid is 0.08, 0.15, 0.39 and 0.38, respectively. The site-occupancy values were obtained by free refinement of carbon or oxygen electron density to give the lowest R factor.

Figure 6
Stacked ¹H NMR plots of the hexacomponent (123456) salt-alloy crystal along with the five carboxylic acid units (2–6, indicated in black font). The resonances corresponding to the individual carboxylic acid components in the spectrum of the hexanary crystal are indicated in red.

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 [R_2^2] (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

Crystal structure: 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: https://doi.org/10.1107/S2052252518014057/ed5016sup1.cif

Supporting tables, figures and schemes. DOI: https://doi.org/10.1107/S2052252518014057/ed5016sup2.pdf

Computing details top

Cell refinement: 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.

(12) top

Crystal data top

C₃₁H₃₄N₂O₅	F(000) = 1096
M_r = 514.60	D_x = 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

Data collection top

SuperNova, Dual, Cu at zero, Eos diffractometer	R_int = 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.	θ_max = 25.0°, θ_min = 3.0°
T_min = 0.726, T_max = 1.000	h = −13→13
24778 measured reflections	k = −21→21
4626 independent reflections	l = −16→16
3831 reflections with I > 2σ(I)

Refinement top

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(F_o²) + (0.0374P)² + 2.5351P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
4626 reflections	Δρ_max = 0.44 e Å⁻³
345 parameters	Δρ_min = −0.29 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(13) top

Crystal data top

C₃₁H₃₄N₂O₆	F(000) = 1128
M_r = 530.60	D_x = 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

Data collection top

SuperNova, Dual, Cu at zero, Eos diffractometer	3368 reflections with I > 2σ(I)
ω scans	R_int = 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.	θ_max = 25.0°, θ_min = 2.9°
T_min = 0.775, T_max = 1.000	h = −13→13
11084 measured reflections	k = −20→13
4667 independent reflections	l = −14→16

Refinement top

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(F_o²) + (0.0452P)² + 2.2386P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
4667 reflections	Δρ_max = 0.32 e Å⁻³
355 parameters	Δρ_min = −0.17 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(14) top

Crystal data top

C₃₁H₃₄N₂O₇	F(000) = 1160
M_r = 546.60	D_x = 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

Data collection top

SuperNova, Dual, Cu at zero, Eos diffractometer	3717 reflections with I > 2σ(I)
ω scans	R_int = 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.	θ_max = 25.0°, θ_min = 3.1°
T_min = 0.801, T_max = 1.000	h = −13→13
11635 measured reflections	k = −15→21
4734 independent reflections	l = −14→15

Refinement top

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(F_o²) + (0.0639P)² + 8.6056P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
4734 reflections	Δρ_max = 0.41 e Å⁻³
365 parameters	Δρ_min = −0.29 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(15) top

Crystal data top

C₃₁H₃₄N₂O₇	F(000) = 1160
M_r = 546.60	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	5449 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 28.7°, θ_min = 2.2°
T_min = 0.687, T_max = 0.746	h = −14→14
66674 measured reflections	k = −24→24
6923 independent reflections	l = −18→18

Refinement top

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(F_o²) + (0.054P)² + 2.0027P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
6923 reflections	Δρ_max = 0.81 e Å⁻³
365 parameters	Δρ_min = −0.35 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(16) top

Crystal data top

C₆₂H₆₇N₄O₁₄	F(000) = 1158
M_r = 1092.19	D_x = 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

Data collection top

SuperNova, Dual, Cu at zero, Eos diffractometer	6342 reflections with I > 2σ(I)
ω scans	R_int = 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.	θ_max = 25.0°, θ_min = 3.0°
T_min = 0.530, T_max = 1.000	h = −13→11
11695 measured reflections	k = −19→20
8293 independent reflections	l = −14→16

Refinement top

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(F_o²) + (0.0705P)² + 0.6067P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.170	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.21 e Å⁻³
8293 reflections	Δρ_min = −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)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(123) top

Crystal data top

C₃₁H₃₄N₂O_5.90	F(000) = 1125
M_r = 529.00	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	6706 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 29.6°, θ_min = 2.3°
T_min = 0.684, T_max = 0.746	h = −15→15
53638 measured reflections	k = −24→24
7114 independent reflections	l = −18→18

Refinement top

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(F_o²) + (0.0668P)² + 0.9174P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
7114 reflections	Δρ_max = 0.44 e Å⁻³
458 parameters	Δρ_min = −0.36 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

(124) top

Crystal data top

C₃₁H_34.42N₂O_6.42	F(000) = 1143
M_r = 537.74	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	5411 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 28.2°, θ_min = 2.5°
T_min = 0.704, T_max = 0.746	h = −15→15
88550 measured reflections	k = −23→23
6635 independent reflections	l = −17→17

Refinement top

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(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
S = 1.62	(Δ/σ)_max < 0.001
6635 reflections	Δρ_max = 0.32 e Å⁻³
365 parameters	Δρ_min = −0.32 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(126) top

Crystal data top

C₆₂H_67.84N₄O_11.72	F(000) = 1123
M_r = 1056.56	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	10798 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 30.5°, θ_min = 2.2°
T_min = 0.679, T_max = 0.746	h = −16→16
65036 measured reflections	k = −24→24
15959 independent reflections	l = −19→19

Refinement top

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(F_o²) + (0.0303P)² + 3.0563P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.163	(Δ/σ)_max = 0.001
S = 1.06	Δρ_max = 0.29 e Å⁻³
15959 reflections	Δρ_min = −0.25 e Å⁻³
730 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Absolute structure parameter: −0.2 (17)

Special details top

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(134) top

Crystal data top

C₃₁H₃₄N₂O_6.51	F(000) = 1144
M_r = 538.76	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	8381 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 33.1°, θ_min = 2.5°
T_min = 0.670, T_max = 0.747	h = −17→16
57701 measured reflections	k = −27→27
9884 independent reflections	l = −18→20

Refinement top

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(F_o²) + (0.0749P)² + 1.0813P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
9884 reflections	Δρ_max = 0.73 e Å⁻³
365 parameters	Δρ_min = −0.36 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(135) top

Crystal data top

C₃₁H_34.55N₂O_6.14	F(000) = 1135
M_r = 533.39	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	6366 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 30.5°, θ_min = 2.6°
T_min = 0.675, T_max = 0.746	h = −15→14
39100 measured reflections	k = −24→25
7888 independent reflections	l = −17→18

Refinement top

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(F_o²) + (0.0397P)² + 2.2439P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
7888 reflections	Δρ_max = 0.35 e Å⁻³
366 parameters	Δρ_min = −0.65 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(136) top

Crystal data top

C₃₁H₃₄N₂O_6.47	F(000) = 1143
M_r = 538.12	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	4598 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 28.3°, θ_min = 2.1°
T_min = 0.345, T_max = 0.746	h = −15→15
76404 measured reflections	k = −23→23
6567 independent reflections	l = −17→17

Refinement top

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(F_o²) + 7.6232P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.003
6567 reflections	Δρ_max = 0.25 e Å⁻³
365 parameters	Δρ_min = −0.34 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(145) top

Crystal data top

C₃₁H₃₄N₂O₇	F(000) = 1160
M_r = 546.60	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	6474 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 30.5°, θ_min = 2.3°
T_min = 0.632, T_max = 0.746	h = −15→13
63575 measured reflections	k = −25→25
8027 independent reflections	l = −19→19

Refinement top

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(F_o²) + (0.0253P)² + 8.2966P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max = 0.004
8027 reflections	Δρ_max = 0.51 e Å⁻³
375 parameters	Δρ_min = −0.38 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(146) top

Crystal data top

C₃₁H₃₃N₂O₇	F(000) = 1156
M_r = 545.59	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	6717 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 30.5°, θ_min = 2.3°
T_min = 0.685, T_max = 0.746	h = −16→16
88884 measured reflections	k = −25→25
8099 independent reflections	l = −18→18

Refinement top

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(F_o²) + (0.0604P)² + 5.8639P] where P = (F_o² + 2F_c²)/3
S = 1.21	(Δ/σ)_max < 0.001
8099 reflections	Δρ_max = 0.58 e Å⁻³
375 parameters	Δρ_min = −0.49 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(1234) top

Crystal data top

C₃₁H_34.12N₂O_6.33	F(000) = 1139
M_r = 536.00	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	R_int = 0.039
φ and ω scans	θ_max = 26.3°, θ_min = 2.5°
62700 measured reflections	h = −14→14
5404 independent reflections	k = −22→22
4670 reflections with I > 2σ(I)	l = −16→16

Refinement top

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(F_o²) + (0.0703P)² + 0.7038P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
5404 reflections	Δρ_max = 0.22 e Å⁻³
431 parameters	Δρ_min = −0.26 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

(1235) top

Crystal data top

C₃₁H₃₄N₂O_6.17	F(000) = 1133
M_r = 533.32	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	5620 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 30.4°, θ_min = 2.3°
T_min = 0.528, T_max = 0.746	h = −15→15
67030 measured reflections	k = −24→25
7947 independent reflections	l = −19→19

Refinement top

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(F_o²) + 9.7346P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.007
7947 reflections	Δρ_max = 0.32 e Å⁻³
365 parameters	Δρ_min = −0.37 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(1236) top

Crystal data top

C₃₁H₃₄N₂O_6.27	F(000) = 1137
M_r = 534.92	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	R_int = 0.050
φ and ω scans	θ_max = 30.5°, θ_min = 2.3°
90604 measured reflections	h = −16→16
8175 independent reflections	k = −25→24
5373 reflections with I > 2σ(I)	l = −19→19

Refinement top

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(F_o²) + (0.0292P)² + 2.3128P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
8175 reflections	Δρ_max = 0.15 e Å⁻³
365 parameters	Δρ_min = −0.18 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(1245) top

Crystal data top

C₃₁H₃₄N₂O_6.46	F(000) = 1143
M_r = 537.96	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	5857 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 28.3°, θ_min = 2.2°
T_min = 0.695, T_max = 0.746	h = −14→14
61552 measured reflections	k = −23→23
6497 independent reflections	l = −17→17

Refinement top

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(F_o²) + (0.0627P)² + 15.8476P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.005
6497 reflections	Δρ_max = 0.41 e Å⁻³
375 parameters	Δρ_min = −0.50 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(1246) top

Crystal data top

C₃₁H₃₄N₂O_6.40	F(000) = 1141
M_r = 537.00	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	4300 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 26.3°, θ_min = 2.3°
T_min = 0.679, T_max = 0.746	h = −14→14
46089 measured reflections	k = −21→22
5487 independent reflections	l = −16→16

Refinement top

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(F_o²) + (0.0212P)² + 2.2798P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
5487 reflections	Δρ_max = 0.16 e Å⁻³
375 parameters	Δρ_min = −0.15 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(1346) top

Crystal data top

C₃₁H₃₄N₂O_6.81	F(000) = 1154
M_r = 543.56	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	R_int = 0.057
φ and ω scans	θ_max = 30.4°, θ_min = 2.3°
69144 measured reflections	h = −16→16
8182 independent reflections	k = −25→25
5170 reflections with I > 2σ(I)	l = −19→19

Refinement top

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(F_o²) + (0.0757P)² + 1.4079P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
8182 reflections	Δρ_max = 0.28 e Å⁻³
375 parameters	Δρ_min = −0.32 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

(1356) top

Crystal data top

C₆₂H_68.91N₄O_13.03	F(000) = 1146
M_r = 1078.60	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	8744 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 30.4°, θ_min = 2.3°
T_min = 0.669, T_max = 0.746	h = −16→16
63374 measured reflections	k = −25→25
16100 independent reflections	l = −18→19

Refinement top

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(F_o²) + (0.0494P)² + 3.0015P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.198	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.54 e Å⁻³
16100 reflections	Δρ_min = −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)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

(1456) top

Crystal data top

C₃₁H₃₄N₂O₇	F(000) = 1160
M_r = 546.60	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	R_int = 0.040
φ and ω scans	θ_max = 26.3°, θ_min = 2.3°
48278 measured reflections	h = −13→14
5387 independent reflections	k = −22→22
4822 reflections with I > 2σ(I)	l = −16→16

Refinement top

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(F_o²) + 4.1944P] where P = (F_o² + 2F_c²)/3
S = 1.19	(Δ/σ)_max < 0.001
5387 reflections	Δρ_max = 0.28 e Å⁻³
395 parameters	Δρ_min = −0.33 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

(12345) top

Crystal data top

C_31.10H_33.33N₂O_6.35	F(000) = 1139
M_r = 536.73	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	6429 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 30.4°, θ_min = 2.6°
T_min = 0.697, T_max = 0.746	h = −15→15
63397 measured reflections	k = −25→25
7929 independent reflections	l = −18→18

Refinement top

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(F_o²) + (0.062P)² + 2.3743P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max < 0.001
7929 reflections	Δρ_max = 0.67 e Å⁻³
378 parameters	Δρ_min = −0.50 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

(12346) top

Crystal data top

C₃₁H₃₄N₂O_6.69	F(000) = 1150
M_r = 541.64	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	6291 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 30.5°, θ_min = 2.3°
T_min = 0.621, T_max = 0.746	h = −16→16
86570 measured reflections	k = −25→25
8037 independent reflections	l = −16→18

Refinement top

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(F_o²) + (0.0149P)² + 5.2044P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.011
8037 reflections	Δρ_max = 0.40 e Å⁻³
375 parameters	Δρ_min = −0.37 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

(12356) top

Crystal data top

C₆₂H_67.80N₄O_12.63	F(000) = 1138
M_r = 1071.08	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	11616 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 29.6°, θ_min = 2.3°
T_min = 0.700, T_max = 0.746	h = −15→15
80672 measured reflections	k = −24→24
14648 independent reflections	l = −18→18

Refinement top

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(F_o²) + (0.064P)² + 1.2266P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.153	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.52 e Å⁻³
14648 reflections	Δρ_min = −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)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

(123456) top

Crystal data top

C₃₁H₃₄N₂O_6.49	F(000) = 1144
M_r = 538.44	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	4387 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 26.3°, θ_min = 2.2°
T_min = 0.645, T_max = 0.745	h = −14→14
31190 measured reflections	k = −21→21
5299 independent reflections	l = −16→16

Refinement top

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(F_o²) + 4.4821P] where P = (F_o² + 2F_c²)/3
S = 1.19	(Δ/σ)_max < 0.001
5299 reflections	Δρ_max = 0.28 e Å⁻³
385 parameters	Δρ_min = −0.24 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

(platon_pl) top

Crystal data top

C₂₄H₂₉N₂O₃·C₇H₅O₅	F(000) = 1192
M_r = 562.60	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	6782 reflections with I > 2σ(I)
φ and ω scans	R_int = 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.	θ_max = 30.5°, θ_min = 1.8°
T_min = 0.708, T_max = 0.746	h = −15→15
104029 measured reflections	k = −25→25
8405 independent reflections	l = −19→19

Refinement top

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(F_o²) + (0.0714P)² + 0.8514P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
8405 reflections	Δρ_max = 0.41 e Å⁻³
375 parameters	Δρ_min = −0.48 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Footnotes

‡Contributed equally to this work.

§Rambabu Dandela and Srinu Tothadi equally contributed to the work

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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IUCrJ

Volume 5| Part 6| November 2018| Pages 816-822

ISSN: 2052-2525

https://doi.org/10.1107/S2052252518014057

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