Quaternary and quinary molecular solids based on structural inequivalence and combinatorial approaches: 2-nitro­resorcinol and 4,6-di­chloro­resorcinol

A synthetic strategy for the formation of stoichiometric quaternary and non­stoichiometric quinary solids is outlined. A series of 2-nitro­resorcinol-based quaternary cocrystals were developed from binary precursors in two conceptual stages. In the first stage, ternary solids are synthesized based on the structural inequivalence at two recognition sites in the binary. In the second stage, the ternary is homologated into a stoichiometric quaternary based on the same concept. Any cocrystal without an inequivalence becomes a synthetic dead end. The combinatorial approach involves lower cocrystal systems with different structural environments and preferred synthon selection from a synthon library in solution. Such are the stepping stones for the isolation of higher cocrystals. In addition, a quaternary cocrystal of 4,6-di­chloro­resorcinol is described wherein an unusual synthon is observed with two resorcinol molecules in a closed loop with two different ditopic bases. The concept of the virtual synthon in binaries with respect to isolated ternaries is validated for the 4,6-di­chloro­resorcinol system. It is possible that only some binary systems are amenable to homologation into higher cocrystals. The reasons for this could have to do with the existence of preferred synthon modules, in other words, the critical components of the putative higher assembly that cannot be altered. Addition of the third and fourth component might be more flexible, and the choices of these com­ponents, possible from a larger pool of chemically related molecules.

1. Introduction

The design of higher-order multicomponent cocrystals (Bond, 2007; Bolla & Nangia, 2015), especially ternaries and quater­naries, is a challenging synthetic exercise (Mir et al., 2019) requiring a proper knowledge of the robustness of specific supramolecular synthons (Desiraju, 1995; Shattock et al., 2008). Any synthetic strategy towards higher cocrystals should be of high supramolecular yield and without contamination from by-products such as binaries and pure compounds. A very limited number of stoichiometric quaternaries (less than 20) have been obtained to date (Bhogala & Nangia, 2008; Dandela et al., 2018; Dubey et al., 2016; Mir et al., 2016; Paul et al., 2018; Paul & Desiraju, 2019). All quaternary cocrystals thus far obtained by our group are based on either structural inequivalences or a combinatorial approach. These higher cocrystal experiments suggest that combinations of resorcinols and methyl­ated pyrazines could be the way forward for general synthetic strategies (Dubey et al., 2016; Mir et al., 2016; Paul et al., 2018; Paul & Desiraju, 2019). The inclusion of a fifth component stoichiometrically within the same crystal still remains an open challenge because with an increasing number of components and functional groups, the number of possible permutations creates very difficult synthetic challenges (Gunawardana & Aakeröy, 2018). In this article, we report seven quaternary and two quinary molecular solids to further strengthen the generality of our synthetic strategy towards higher cocrystals.

The structural inequivalence strategy (Mir et al., 2016) is an outcome of molecule selection by the chemist in that if any particular molecule is bound at two distinct crystallographic environments in a (lower) cocrystal structure, this distinction can be exploited to homologate into a higher cocrystal by substituting a new, but similar, molecule at the more loosely bound site. This structural inequivalence is always integrated with a graded interaction hierarchy (Aakeröy et al., 2001). On the other hand, the combinatorial strategy (Dubey & Desiraju, 2014) depends on the fact that if a molecule persists in many forms (polymorphs and/or pseudopolymorphs, the latter being essentially stoichiometric variants), crystallization of such a molecule with another component can lead to a higher cocrystal which is anticipated with a selection of the fittest interactions that are possible from a pool of multiple competing interactions for this particular molecule.

2. Results and discussion

Our approach to the design of quaternary and quinary molecular solids of 2-nitro­resorcinol (NRES) is based on the simultaneous use of chemical (interaction-based) and geometrical (shape- and size-based) recognition information (Aakeröy et al., 2007; Moorthy et al., 2010). The compounds used in this study with acronyms are given in Fig. 1 and the synthetic strategy involved in the quaternary cocrystal synthesis for NRES:TMP:PYR:ACR and NRES:TMP:PYR:4DMAP is presented in Fig. 2. In these quaternaries, the binary cocrystal of NRES with tetra­methyl­pyrazine (TMP) is the basic template. In our hands, this binary cocrystal was obtained in two pseudopolymorphic variants. The first is a 2:1 form that crystallizes in the space group P1. The second is a 2:3 form which crystallizes in the space group P. Details of these two cocrystals are given in the supporting information. Because the TMP molecules are located on pseudocentres of symmetry in the noncentrosymmetric 2:1 form, adequate care was taken in the space-group assignment.

Figure 1 Compounds used in this study with acronyms.

Figure 2 Synthetic strategy for the preparation of the NRES:TMP:PYR:ACR and NRES:TMP:PYR:4DMAP quaternary cocrystals. Colour coding and shapes represent distinct chemical and geometrical features of the molecules.

In any event, the connectivity of the TMP and NRES molecules is the same in both of these cocrystals and, most significantly, the TMP molecule is found in two distinct crystallographic environments in both cases. Of the two TMP molecules, one is connected to NRES only via O—H⋯N hydrogen bonds to give an infinite one-dimensional (1D) chain, while the other is additionally involved in weak C—H⋯O, C—H⋯π and π–π interactions with adjacent NRES molecules. As C—H⋯O, C—H⋯π and π–π interactions are comparable in strength, a PYR molecule, which has the capability of forming a C—H⋯π interaction with TMP, may be incorporated as the third component (replacing the NRES that bonds weakly via C—H⋯O). In this ternary, and as prescribed, the PYR molecule is connected with one of the two TMP molecules through C—H⋯π interactions, while the other is still unaffected; accordingly, a fourth component, which may be either ACR or 4DMAP, may be introduced with interaction substitution to homologate to the quaternaries NRES:TMP:PYR:ACR and NRES:TMP:PYR:4DMAP (Fig. 3). In both cases, the monotopic bases ACR and 4DAMAP are connected at the two ends of the assembly but these become synthetic dead ends for homologation into quinaries. In other words, since inequivalences were not found in any of the quaternaries we isolated, stoichiometric inclusion of a fifth component with this strategy is not possible.

Figure 3 The development of the NRES:TMP:PYR:ACR and NRES:TMP:PYR:4DMAP quaternaries from the NRES:TMP:PYR ternary in which one of the TMP molecules is replaced by a fourth component, ACR or 4DMAP, using O—H⋯N hydrogen bonding.

While developing these quaternaries, two ternaries were simultaneously obtained, namely, NRES:4DMAP:PYR and NRES:TMP:DPE-I. Let us first consider the former. Crystallization of NRES with 4DMAP gave a 1:1 cocrystal and a 1:1 binary salt (from MeOH and MeCN, respectively). In the cocrystal, the two components are connected via O—H⋯.N hydrogen bonding at each hydroxy-group end of NRES; in the salt, the NRES molecules are linked to one another via O—H⋯O hydrogen bonds to form a chain, while 4DMAP molecules are connected to them via N—H⋯O hydrogen bonds. In the next step, PYR is added to the binary mixture to obtain a ternary in which PYR is stacked with 4DMAP through a C—H⋯π interaction. The other ternary, NRES:TMP:DPE-I, was obtained when the ternary mixture NRES:TMP:PYR was crystallized with DPE-I (to obtain a quaternary). This procedure removed the PYR molecule and an entirely different supramolecular topology was obtained in the resulting ternary. In this cocrystal, DPE-I is O—H⋯N hydrogen bonded at its two ends to NRES, which uses its other hy­droxy group to connect with TMPs, which terminates the sequence (the second heterocyclic N atom of TMP is `free'). Employing the structural inequivalence approach, Komisarek et al. (2020) have reported this kind of synthon in the system 2-methyl­resorcinol--TMP--DPE-I. In both of these ternaries (NRES:4DMAP:PYR and NRES:TMP:DPE-I), no inequivalences are observed at any of the chemically identical sites and therefore these cannot be exploited for further homologation. Both ternaries are synthetic dead ends.

Let us next consider the synthetic strategy towards quinary cocrystals from quaternaries (Fig. 4). Here, the binary NRES:TMP (mentioned previously) is crystallized with either 2,2′-bi­pyridine (22BP) or 2,2′-bi­thio­phene (22TBP) to give the ternaries NRES:TMP:22BP and NRES:TMP:22TBP in 1:2:2 and 1:2:4 stoichiometries, respectively. In these ternary systems, it is found that the two TMP molecules flanking NRES are in different crystallographic environments (as seen previously with PYR). In NRES:TMP:22BP, of the two TMP molecules, one forms C—H⋯π interactions with 22BP, while the other is not involved in any such interaction; accordingly, the latter may be replaced by other ditopic N-atom donors. In NRES:TMP:22TBP, there is a similar situation. These differences are sufficient for the replacement of such `free' molecules by another N-atom donor. Accordingly, in the next homologation step, each of these ternaries was crystallized with DPE-I or DPE-II, so that we successfully obtained four 1:1:1:1 quaternaries, namely, NRES:TMP:22BP:DPE-I and NRES:TMP:22BP:DPE-II with 22BP, and cor­respondingly NRES:TMP:22TBP:DPE-I and NRES:TMP:22TBP:DPE-II with 22TBP. These quaternaries are, however, syn­thetic dead ends and structural inequivalences may no longer be used to homologate to the quinary stage.

Figure 4 Proposed schemes for the construction of five-component systems.

A careful analysis of these quaternary structures paved the way to include a fifth component in these systems. In this context, the phenyl/thiophenyl exchange rule is relevant (Thallapally et al., 2000; Tothadi et al., 2011). According to this concept, 2,2′-bi­thio­phene, 2,2′-bi­phenyl and 2,2′-bi­pyridine are volume equivalents (–S– ≃ –CH=CH– ≃ –CH=N–) and so are mutually exchangeable in a crystal structure. The question arises therefore as to whether it might be possible to obtain quinary cocrystals if both 2,2′-bi­thio­phene and 2,2′-bi­pyridine are taken together along with the other three components NRES:TMP:DPE-I. Accordingly, we ground NRES, TMP and DPE-I with 0.5:0.5 ratios of 22BP and 22TBP, and isolated a five-component solid-solution cocrystal (Fig. 5). We carried out a similar crystallization experiment with DPE-II and obtained the corresponding five-component solid-solution cocrystal NRES:TMP:22BP:22TBP:DPE-II.

Figure 5 Quinaries NRES:TMP:22TBP:22BP:DPE-I and NRE:TMP:22TBP:22BP:DPE-II. Note that the fourth and fifth components are included in a solid-solution manner.

To confirm the existence of five different organic molecules in the same crystal, we carried out GC–MS (gas chromatography–mass spectrometry) analysis. For this, single crystals of the quinary system were dissolved in MeOH. We observed five different peaks at different retention times (Fig. 6; the very small peak is an unknown impurity, possibly from stopcock grease).

Figure 6 GCMS spectra of five-component systems.

We now discuss the combinatorial synthetic strategy based on long-range synthon Aufbau modules (LSAM) in the higher cocrystals of 4,6-di­chloro­resorcinol. The modular nature of the interactions may be utilized to obtain higher cocrystals by adding and/or exchanging a new molecule in the LSAM of the lower cocrystals. A putative supramolecular synthon of 4,6-di­chloro­resorcinol with complementary N-atom donors is illustrated in Fig. 7 and a schematic representation of the synthesis of quaternary cocrystals is shown in Fig. 8.

Figure 7 Possible supramolecular synthons of the 4,6-di­chloro­resorcinol system with N-atom donors. CRES is shown in green and blue and red are ditopic bases. Note that synthon A (seen elsewhere) is not observed in this study. Synthon D, which is unsymmetrical, is rarely seen with resorcinols in general (Paul & Desiraju, 2019).

Figure 8 A cartoon representation of the synthetic strategy for the CRES quaternary. Distinct chemical species are given with different shapes and in different colours.

In this attempt, we obtained three each of the binary and ternary cocrystals, and one quaternary cocrystal. Crystallization of CRES with (one of) TMP, PHE or DMP resulted in a stoichiometric binary cocrystal. In the 1:1 CRES:TMP cocrystal, the TMP molecules form discrete synthon C (closed CRES:TMP tetramer synthons, the so-called MacGillivray synthon) (Papaefstathiou et al., 2001; Ghorai et al., 2013) that are laterally offset with respect to one another. Next, we observed the formation of an unusual open synthon in the 1:3 CRES:PHE binary in which one hydroxy group of the CRES molecule is connected to two PHE molecules through O—H⋯N hydrogen bonding, followed by C—H⋯N interactions, while the second hydroxy group of CRES is linked to three PHE molecules so as to form a continuous 1D LSAM (Fig. 9). These open synthons are further stacked with π–π interactions between PHE molecules. The CRES:DMP binary forms another kind of continuous 1D LSAM in which the two DMP molecules that are connected to CRES are perpendicular to each other, leading to C—H⋯π interactions. In all these binaries, we found that there are some weak interactions (C—H⋯O, π—π and C—H⋯π) which may be opened further to obtain higher cocrystals.

Figure 9 Binary cocrystals with synthons B and C. Note that CRES:PHE shows an unusual open synthon.

Accordingly, in the next homologation experiment, the PYR molecule was incorporated within these binaries and this resulted in three distinct ternaries. Interestingly, although binaries with closed synthon C were not isolated (say in CRES:PHE and CRES:DMP), all ternaries in this system have the closed synthon C wherein both bases are the same (Fig. 10). This suggests the idea of a virtual synthon which, while it exists in solution, is only manifested in some isolated cocrystals in the entire system. Such a synthon is virtual with respect to binary crystallization and becomes real with respect to ternary systems (Dubey & Desiraju, 2014). Exploiting the similarities of the synthons in these ternary systems, three attempts at homologation were made: (i) CRES:TMP:PYR with PHE; (ii) CRES:TMP:PYR with DMP; and (iii) CRES:DMP:PYR with PHE. In the process of crystallizing CRES:TMP:PYR with PHE, two distinguishable crystals differing in colour (red and yellow) were obtained from the same solution. The red crystal was identified as the ternary CRES:PHE:PYR and the yellow crystal as the quaternary CRES:TMP:PYR:PHE (Fig. 11). This quaternary cocrystal contains the anomalous MacGillivray synthon (Paul & Desiraju, 2019) (synthon D) with two different bases (TMP and PHE). Crystallization according to protocols (ii) and (iii) above did not prove fruitful. The crystallographic details of all the cocrystals used are provided in the supporting information.

Figure 10 The 2:2:1 stoichiometric ternary cocrystals with synthon C, i.e. (a) CRES:TMP:PYR, (b) CRES:PHE:PYR and (c) CRES:DMP:PYR.

Figure 11 The structure of the quaternary cocrystal CRES:PHE:TMP:PYR with the unusual synthon D. The inset photograph shows the simultaneous growth of the quaternary (red) and ternary (yellow) crystals from a solution containing CRES, PHE, TMP and PYR.

3. Conclusions

The results obtained in this work validate the structural inequivalence and combinatorial approaches for the isolation of quaternary molecular solids and the use of such approaches combined with solid-solution methods for the achieving of quinary solids, providing more synthetic generality. In the present study, six stoichiometric quaternaries and two non­stoichiometric quinary cocrystals are reported based on the structural inequivalence approach. The two-component combinations of TMP:PYR, TMP:22BP and TMP:22TBP play a pivotal role in the formation of quaternary cocrystals in which there are C—H⋯π interactions. In the case of the NRES:TMP:PYR ternary, monotopic N-atom donors are required for the formation of quaternary cocrystals, whereas in the case of NRES:TMP:22BP and NRES:TMP:22TBP, symmetrical ditopic N-atom donors are required. After reaching synthetic dead ends at the quaternary level, the concept of shape–size similarity was utilized as a synthetic tool for obtaining five-component systems. In addition, an interesting quaternary cocrystal was obtained based on the combinatorial approach in which an unusual tetramer synthon, containing two different bases, was obtained. Finally, a closed supramolecular synthon, which was not observed in binary cocrystals, appears at the ternary and quaternary levels, strengthening the concept of virtual synthons in solution.

The formation of higher cocrystals (ternary and higher) poses restrictions on exactly what molecular precursors are chosen, and on what exactly are the experimental conditions of the crystallization experiment. Many of these choices may be, in the end, arbitrary, especially regarding the solvents chosen and the temperatures and cooling rates employed. Of course, the latter experimental variables are critical in many crystallizations, including in some of the simplest single-substance experiments, as they depend on the details of the relevant solvent–solute phase diagrams. What is of relevance here is to ascertain if certain compounds or types of compounds are more amenable to the formation of higher cocrystals than others. Expectedly, polyfunctional compounds such as diphenols, triphenols and ditopic bases were found to be suitable. In the course of our work in this area over the past decade, we have found that a combination of a 2-substituted (or other) resorcinol with TMP is generally required to form ternary and higher cocrystals. There are a few exceptions but the above is largely true across many crystallization experiments that have led to the isolation and characterization of around 75 ternaries and 20 quaternaries. The present study is no exception to these general trends. There is some latitude in the nature of the 2-substituent in the resorcinol component (or the other substituents) for higher cocrystals to be formed but TMP seems to be necessary. It is seen that both tri­methyl­pyrazine and 2,5-di­methyl­pyrazine form binaries with 2-sub­stituted resorcinols, but these cannot be homologated. On the other hand, there is considerable flexibility in the choice of the third and fourth component once resorcinol and TMP are selected as two of the components in the crystallization experiment. These can be chosen from several heterocyclic and nonheterocyclic bases, and from condensed ring hydro­carbons that are usually C—H⋯π stacked on the TMP.

These results suggest the relevance of the resorcinol–TMP association, which seems to be the basic building block of higher architectures through synthons of types A through D (Fig. 7). Why such synthons are important for homologation is not clear, and especially why TMP itself seems to be so important is unknown. It is possible that these small synthons can expand easily into LSAMs that incorporate the third and fourth component, but again the specificity of synthons A through D is not easy to rationalize. More high-throughput crystallizations involving combinatorial and robotic methods may prove to be the route to expanding the structural space occupied by stoichiometric ternary and quaternary cocrystals. However, what seems clear enough is that there exist a vast number of higher cocrystals that remain to be discovered.

Supporting information

Computing details

Program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014) for 2NRES-TMP, 5NRES-9AACR, 8NRES-DPE-I, 9NRES-DPE-II, 10NRES-44AZO, 12NRES-4DMAP-II, 13NRES-TMP-PYR, 14NRES-4DMAP-PYR, 15NRES-TMP-DPE-I, 17NRE-TMP-22TBP, 20NRES-TMP-22BP-DPE-I, 26CRES-TMP, 27CRES-PHE, 28CRES-DMP, 30CRES-PHE-PYR, 31CRES-DMP-PYR, 32CRES-TMP-PHE-PYR; SHELXT 2014/4 (Sheldrick, 2014) for 25NRES-TMP-22BP-22TBP-DPE-II. Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2014) for 1NRES-TMP; SHELXL2018/3 (Sheldrick, 2018) for 2NRES-TMP, 3NRES-ACR, 4NRES-DMP, 5NRES-9AACR, 6NRES-33BP, 7NRES-44BP, 8NRES-DPE-I, 9NRES-DPE-II, 10NRES-44AZO, 11NRES-4DMAP, 12NRES-4DMAP-II, 13NRES-TMP-PYR, 14NRES-4DMAP-PYR, 15NRES-TMP-DPE-I, 16NRES-TMP-22BP, 17NRE-TMP-22TBP, 18NRES-TMP-PYR-ACR, 19NTES-TMP-PYR-4DMAP, 20NRES-TMP-22BP-DPE-I, 21NRES-TMP-22BP-DPE-II, 22NRES-TMP-22TBP-DPE-I, 23NRES-TMP-22TBP-DPE-II, 24NRES-TMP-22BP-22TBP-DPE-I, 25NRES-TMP-22BP-22TBP-DPE-II, 26CRES-TMP, 27CRES-PHE, 28CRES-DMP, 29CRES-TMP-PYR, 30CRES-PHE-PYR, 31CRES-DMP-PYR, 32CRES-TMP-PHE-PYR.

(1NRES-TMP)

Crystal data

C20H22N4O8	Z = 2
Mr = 446.41	F(000) = 468
Triclinic, P1	Dx = 1.410 Mg m^−3
a = 7.7162 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9727 (9) Å	Cell parameters from 10074 reflections
c = 16.9089 (17) Å	θ = 3.0–27.6°
α = 86.559 (6)°	µ = 0.11 mm^−1
β = 78.838 (6)°	T = 150 K
γ = 66.314 (5)°	Block, yellow
V = 1051.59 (19) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	7362 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.017
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	θmax = 27.5°, θmin = 3.0°
Tmin = 0.846, Tmax = 1.000	h = −9→10
10971 measured reflections	k = −11→11
9240 independent reflections	l = −21→21

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 0.8048P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.127	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.27 e Å^−3
9240 reflections	Δρmin = −0.24 e Å^−3
612 parameters	Absolute structure: Refined as an inversion twin.
3 restraints	Absolute structure parameter: −0.6 (15)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O13	0.2403 (5)	0.7004 (4)	0.0925 (2)	0.0295 (7)
O14	0.2482 (5)	1.1162 (4)	−0.0863 (2)	0.0330 (8)
O15	0.0087 (5)	0.9269 (4)	−0.0605 (2)	0.0341 (8)
O16	−0.0640 (5)	1.0132 (5)	0.0624 (2)	0.0497 (11)
N2	0.0530 (5)	0.9533 (4)	0.0011 (2)	0.0237 (8)
C12	0.3460 (6)	0.7766 (5)	0.0508 (3)	0.0228 (9)
C8	0.3528 (6)	0.9931 (5)	−0.0441 (3)	0.0224 (9)
C9	0.5491 (6)	0.9460 (6)	−0.0430 (3)	0.0253 (10)
H9	0.6180	1.0011	−0.0732	0.030*
C7	0.2572 (6)	0.9049 (5)	0.0029 (3)	0.0215 (9)
C11	0.5414 (6)	0.7308 (6)	0.0500 (3)	0.0285 (10)
H11	0.6067	0.6435	0.0804	0.034*
C10	0.6379 (6)	0.8167 (6)	0.0036 (3)	0.0274 (10)
H10	0.7681	0.7855	0.0039	0.033*
O1	0.9754 (6)	0.6516 (5)	0.7402 (3)	0.0526 (11)
O2	1.0996 (8)	0.0875 (5)	0.6836 (3)	0.0672 (13)
H2	1.1533	0.1053	0.6395	0.101*
O3	1.1866 (5)	0.4996 (5)	0.6081 (2)	0.0493 (10)
O4	1.2108 (7)	0.2629 (5)	0.5789 (3)	0.0688 (13)
N4	1.1520 (6)	0.3796 (6)	0.6272 (3)	0.0411 (11)
C19	1.0447 (7)	0.3712 (6)	0.7054 (3)	0.0377 (11)
C20	0.9642 (8)	0.5062 (7)	0.7585 (3)	0.0431 (14)
C22	0.8506 (9)	0.3498 (11)	0.8565 (4)	0.067 (2)
H22	0.7852	0.3427	0.9080	0.080*
C21	0.8662 (8)	0.4932 (9)	0.8349 (3)	0.0566 (17)
H21	0.8117	0.5815	0.8708	0.068*
C23	0.9266 (9)	0.2149 (9)	0.8063 (4)	0.0622 (18)
H23	0.9117	0.1197	0.8235	0.075*
C24	1.0248 (9)	0.2230 (7)	0.7301 (4)	0.0499 (15)
O5	0.7411 (5)	0.6261 (4)	0.6045 (2)	0.0300 (8)
O6	0.7682 (5)	1.0207 (4)	0.4128 (2)	0.0310 (8)
O8	0.9636 (5)	0.8369 (4)	0.58108 (19)	0.0300 (7)
O7	1.0709 (5)	0.7287 (4)	0.4619 (2)	0.0351 (8)
N3	0.9395 (5)	0.7946 (4)	0.5183 (2)	0.0222 (8)
C3	0.4588 (6)	0.7747 (5)	0.5461 (3)	0.0251 (10)
H3	0.3890	0.7203	0.5765	0.030*
C2	0.6454 (6)	0.7394 (5)	0.5556 (3)	0.0213 (9)
C6	0.6616 (6)	0.9427 (5)	0.4541 (3)	0.0233 (9)
C1	0.7433 (6)	0.8259 (5)	0.5087 (2)	0.0196 (9)
C5	0.4746 (7)	0.9750 (6)	0.4458 (3)	0.0276 (10)
H5A	0.4160	1.0525	0.4096	0.033*
C4	0.3755 (7)	0.8906 (6)	0.4918 (3)	0.0286 (10)
H4	0.2502	0.9125	0.4860	0.034*
O10	0.0478 (6)	0.0879 (5)	0.2066 (3)	0.0436 (9)
O12	−0.0521 (8)	0.3087 (6)	0.1000 (3)	0.0713 (14)
O11	−0.0531 (7)	0.5450 (6)	0.1136 (3)	0.0694 (14)
O9	−0.0419 (7)	0.6486 (5)	0.2502 (3)	0.0676 (13)
H9A	−0.0674	0.6619	0.2047	0.101*
N1	−0.0378 (7)	0.4107 (6)	0.1414 (3)	0.0468 (12)
C15	0.0203 (7)	0.4565 (7)	0.3504 (4)	0.0490 (15)
H15	0.0153	0.5364	0.3844	0.059*
C16	0.0572 (7)	0.3014 (7)	0.3783 (3)	0.0411 (13)
H16	0.0765	0.2782	0.4311	0.049*
C18	0.0351 (6)	0.2127 (6)	0.2507 (3)	0.0304 (11)
C13	−0.0041 (7)	0.3726 (6)	0.2227 (3)	0.0355 (11)
C17	0.0661 (7)	0.1784 (6)	0.3289 (3)	0.0370 (11)
H17	0.0928	0.0740	0.3485	0.044*
C14	−0.0094 (7)	0.4948 (6)	0.2724 (4)	0.0412 (13)
N5	0.5430 (5)	0.4698 (4)	0.6985 (2)	0.0228 (8)
N6	0.4206 (5)	0.2833 (4)	0.8119 (2)	0.0219 (8)
C32	0.6938 (8)	0.2482 (6)	0.5993 (3)	0.0326 (11)
H32A	0.6101	0.2325	0.5684	0.049*
H32B	0.7981	0.1459	0.6044	0.049*
H32C	0.7442	0.3236	0.5726	0.049*
C28	0.2633 (8)	0.5079 (6)	0.9097 (3)	0.0351 (11)
H28A	0.1474	0.5992	0.9033	0.053*
H28B	0.3380	0.5425	0.9378	0.053*
H28C	0.2309	0.4259	0.9401	0.053*
C29	0.5649 (8)	0.0434 (6)	0.7240 (3)	0.0379 (12)
H29A	0.6982	−0.0213	0.7250	0.057*
H29B	0.5381	0.0317	0.6721	0.057*
H29C	0.4859	0.0077	0.7650	0.057*
C25	0.3960 (8)	0.7096 (6)	0.7856 (3)	0.0355 (12)
H25A	0.4528	0.7522	0.7390	0.053*
H25B	0.4480	0.7189	0.8313	0.053*
H25C	0.2591	0.7702	0.7961	0.053*
C31	0.5828 (6)	0.3145 (5)	0.6814 (3)	0.0238 (9)
C27	0.3785 (6)	0.4391 (5)	0.8282 (3)	0.0226 (9)
C26	0.4401 (6)	0.5343 (5)	0.7703 (3)	0.0229 (9)
C30	0.5220 (6)	0.2188 (5)	0.7393 (3)	0.0233 (9)
N8	0.4285 (5)	0.4716 (4)	0.1947 (2)	0.0251 (8)
N7	0.5741 (5)	0.2446 (4)	0.3074 (2)	0.0235 (8)
C37	0.4592 (8)	0.2652 (6)	0.0994 (3)	0.0342 (11)
H37A	0.3927	0.3614	0.0714	0.051*
H37B	0.3866	0.1983	0.1077	0.051*
H37C	0.5841	0.2055	0.0678	0.051*
C36	0.3792 (8)	0.6985 (6)	0.2802 (3)	0.0380 (12)
H36A	0.3530	0.7553	0.2311	0.057*
H36B	0.4785	0.7188	0.2982	0.057*
H36C	0.2643	0.7360	0.3207	0.057*
C33	0.5342 (7)	0.4498 (6)	0.4038 (3)	0.0317 (11)
H33A	0.4092	0.4911	0.4378	0.047*
H33B	0.5853	0.5321	0.3977	0.047*
H33C	0.6186	0.3557	0.4278	0.047*
C38	0.4811 (6)	0.3123 (5)	0.1793 (3)	0.0230 (9)
C34	0.5176 (6)	0.4036 (5)	0.3229 (3)	0.0228 (9)
C35	0.4445 (6)	0.5192 (5)	0.2654 (3)	0.0242 (10)
C39	0.5556 (6)	0.1978 (5)	0.2366 (3)	0.0226 (9)
C40	0.6157 (8)	0.0185 (6)	0.2227 (3)	0.0348 (12)
H40A	0.7030	−0.0419	0.2578	0.052*
H40B	0.6783	−0.0099	0.1676	0.052*
H40C	0.5040	−0.0072	0.2339	0.052*
H5	0.656 (9)	0.569 (7)	0.636 (4)	0.058 (19)*
H6	0.714 (8)	1.079 (6)	0.382 (3)	0.031 (15)*
H13	0.321 (10)	0.617 (8)	0.125 (4)	0.07 (2)*
H14	0.302 (7)	1.165 (6)	−0.107 (3)	0.027 (14)*
H10A	0.017 (10)	0.117 (8)	0.164 (4)	0.06 (2)*
H1	1.026 (8)	0.645 (7)	0.694 (3)	0.032 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O13	0.0295 (18)	0.0290 (17)	0.0341 (18)	−0.0167 (14)	−0.0090 (14)	0.0161 (14)
O14	0.0281 (18)	0.0293 (18)	0.044 (2)	−0.0163 (15)	−0.0083 (15)	0.0221 (16)
O15	0.0290 (17)	0.045 (2)	0.0342 (19)	−0.0177 (15)	−0.0150 (15)	0.0076 (15)
O16	0.0210 (17)	0.075 (3)	0.043 (2)	−0.0109 (18)	0.0048 (16)	−0.018 (2)
N2	0.0191 (18)	0.0221 (18)	0.032 (2)	−0.0102 (15)	−0.0079 (16)	0.0102 (16)
C12	0.023 (2)	0.022 (2)	0.025 (2)	−0.0114 (18)	−0.0055 (18)	0.0048 (18)
C8	0.024 (2)	0.018 (2)	0.024 (2)	−0.0090 (18)	−0.0022 (18)	0.0035 (17)
C9	0.023 (2)	0.030 (2)	0.027 (2)	−0.0165 (19)	−0.0017 (18)	0.0059 (19)
C7	0.019 (2)	0.019 (2)	0.027 (2)	−0.0084 (17)	−0.0048 (18)	0.0007 (17)
C11	0.023 (2)	0.030 (2)	0.032 (2)	−0.0072 (19)	−0.0107 (19)	0.0083 (19)
C10	0.017 (2)	0.032 (2)	0.035 (2)	−0.0104 (19)	−0.0075 (18)	0.003 (2)
O1	0.056 (3)	0.048 (2)	0.049 (3)	−0.010 (2)	−0.021 (2)	−0.005 (2)
O2	0.081 (3)	0.040 (2)	0.085 (3)	−0.019 (2)	−0.040 (3)	0.009 (2)
O3	0.038 (2)	0.048 (2)	0.056 (2)	−0.0126 (18)	−0.0074 (18)	0.0117 (19)
O4	0.082 (3)	0.054 (3)	0.052 (3)	−0.012 (2)	−0.001 (2)	−0.016 (2)
N4	0.031 (2)	0.044 (3)	0.037 (2)	−0.002 (2)	−0.0123 (19)	0.005 (2)
C19	0.028 (2)	0.044 (3)	0.036 (3)	−0.006 (2)	−0.016 (2)	0.006 (2)
C20	0.033 (3)	0.053 (4)	0.041 (3)	−0.010 (3)	−0.018 (2)	0.003 (3)
C22	0.045 (4)	0.109 (6)	0.042 (4)	−0.027 (4)	−0.019 (3)	0.036 (4)
C21	0.040 (3)	0.085 (5)	0.034 (3)	−0.009 (3)	−0.015 (2)	−0.004 (3)
C23	0.050 (4)	0.075 (5)	0.067 (4)	−0.026 (3)	−0.033 (3)	0.037 (4)
C24	0.048 (3)	0.051 (4)	0.055 (4)	−0.016 (3)	−0.034 (3)	0.019 (3)
O5	0.0271 (17)	0.0297 (17)	0.0368 (19)	−0.0145 (14)	−0.0122 (14)	0.0172 (14)
O6	0.0261 (17)	0.0343 (19)	0.0366 (19)	−0.0168 (15)	−0.0100 (15)	0.0191 (15)
O8	0.0289 (17)	0.0364 (18)	0.0282 (17)	−0.0136 (14)	−0.0113 (14)	−0.0023 (14)
O7	0.0214 (16)	0.045 (2)	0.0341 (18)	−0.0106 (15)	0.0026 (14)	−0.0053 (15)
N3	0.0205 (19)	0.0224 (18)	0.0254 (19)	−0.0099 (15)	−0.0065 (15)	0.0061 (15)
C3	0.023 (2)	0.025 (2)	0.030 (2)	−0.0144 (19)	−0.0039 (19)	0.0062 (19)
C2	0.023 (2)	0.020 (2)	0.023 (2)	−0.0103 (17)	−0.0046 (17)	0.0016 (17)
C6	0.025 (2)	0.023 (2)	0.023 (2)	−0.0112 (18)	−0.0035 (18)	0.0029 (17)
C1	0.017 (2)	0.018 (2)	0.023 (2)	−0.0067 (17)	−0.0035 (17)	0.0029 (16)
C5	0.024 (2)	0.028 (2)	0.030 (2)	−0.0097 (19)	−0.0104 (18)	0.0130 (19)
C4	0.022 (2)	0.034 (3)	0.033 (2)	−0.013 (2)	−0.0102 (19)	0.003 (2)
O10	0.049 (2)	0.038 (2)	0.047 (2)	−0.0184 (18)	−0.0138 (19)	0.0005 (18)
O12	0.092 (4)	0.081 (3)	0.059 (3)	−0.044 (3)	−0.042 (3)	0.022 (2)
O11	0.061 (3)	0.067 (3)	0.098 (4)	−0.037 (2)	−0.042 (3)	0.051 (3)
O9	0.050 (3)	0.026 (2)	0.120 (4)	−0.0109 (18)	−0.012 (3)	0.003 (2)
N1	0.031 (2)	0.054 (3)	0.058 (3)	−0.018 (2)	−0.018 (2)	0.019 (2)
C15	0.030 (3)	0.048 (3)	0.065 (4)	−0.015 (2)	0.007 (3)	−0.021 (3)
C16	0.028 (3)	0.054 (3)	0.040 (3)	−0.015 (2)	−0.003 (2)	−0.005 (3)
C18	0.019 (2)	0.032 (3)	0.041 (3)	−0.0111 (19)	−0.005 (2)	0.000 (2)
C13	0.024 (2)	0.034 (3)	0.048 (3)	−0.011 (2)	−0.007 (2)	0.007 (2)
C17	0.026 (2)	0.038 (3)	0.043 (3)	−0.010 (2)	−0.005 (2)	0.003 (2)
C14	0.024 (3)	0.033 (3)	0.063 (4)	−0.008 (2)	−0.005 (2)	−0.002 (3)
N5	0.029 (2)	0.0194 (17)	0.0234 (19)	−0.0110 (15)	−0.0102 (15)	0.0076 (14)
N6	0.0261 (19)	0.0200 (17)	0.0211 (18)	−0.0111 (15)	−0.0050 (15)	0.0044 (14)
C32	0.045 (3)	0.026 (2)	0.024 (2)	−0.015 (2)	0.001 (2)	−0.0002 (18)
C28	0.051 (3)	0.036 (3)	0.019 (2)	−0.023 (2)	0.005 (2)	−0.0006 (19)
C29	0.055 (3)	0.018 (2)	0.040 (3)	−0.019 (2)	0.001 (2)	−0.001 (2)
C25	0.046 (3)	0.022 (2)	0.041 (3)	−0.016 (2)	−0.006 (2)	0.003 (2)
C31	0.028 (2)	0.023 (2)	0.023 (2)	−0.0120 (19)	−0.0084 (18)	0.0055 (17)
C27	0.027 (2)	0.021 (2)	0.021 (2)	−0.0105 (18)	−0.0064 (17)	0.0037 (17)
C26	0.029 (2)	0.020 (2)	0.024 (2)	−0.0127 (18)	−0.0074 (18)	0.0049 (17)
C30	0.029 (2)	0.018 (2)	0.026 (2)	−0.0112 (18)	−0.0082 (18)	0.0032 (17)
N8	0.026 (2)	0.0213 (19)	0.0237 (19)	−0.0064 (16)	−0.0022 (15)	0.0042 (15)
N7	0.0187 (18)	0.0241 (19)	0.0246 (19)	−0.0072 (15)	−0.0013 (15)	0.0050 (15)
C37	0.036 (3)	0.032 (3)	0.028 (2)	−0.005 (2)	−0.009 (2)	0.000 (2)
C36	0.052 (3)	0.023 (2)	0.039 (3)	−0.015 (2)	−0.008 (2)	0.003 (2)
C33	0.032 (3)	0.036 (3)	0.025 (2)	−0.011 (2)	−0.009 (2)	0.001 (2)
C38	0.021 (2)	0.020 (2)	0.026 (2)	−0.0077 (18)	−0.0011 (18)	0.0015 (17)
C34	0.018 (2)	0.025 (2)	0.022 (2)	−0.0068 (18)	−0.0010 (17)	0.0017 (17)
C35	0.023 (2)	0.021 (2)	0.026 (2)	−0.0089 (18)	−0.0011 (18)	0.0027 (17)
C39	0.019 (2)	0.022 (2)	0.023 (2)	−0.0075 (18)	0.0002 (17)	0.0070 (17)
C40	0.039 (3)	0.023 (2)	0.036 (3)	−0.010 (2)	0.000 (2)	0.005 (2)

Geometric parameters (Å, º)

O13—C12	1.341 (6)	N1—C13	1.443 (7)
O13—H13	0.98 (7)	C15—C16	1.377 (8)
O14—C8	1.339 (5)	C15—C14	1.380 (8)
O14—H14	0.75 (5)	C15—H15	0.9300
O15—N2	1.220 (5)	C16—C17	1.396 (7)
O16—N2	1.222 (5)	C16—H16	0.9300
N2—C7	1.463 (5)	C18—C17	1.384 (7)
C12—C7	1.386 (6)	C18—C13	1.414 (7)
C12—C11	1.392 (6)	C13—C14	1.405 (7)
C8—C7	1.403 (6)	C17—H17	0.9300
C8—C9	1.403 (6)	N5—C26	1.334 (6)
C9—C10	1.377 (6)	N5—C31	1.339 (5)
C9—H9	0.9300	N6—C27	1.334 (5)
C11—C10	1.388 (7)	N6—C30	1.343 (6)
C11—H11	0.9300	C32—C31	1.497 (6)
C10—H10	0.9300	C32—H32A	0.9600
O1—C20	1.355 (7)	C32—H32B	0.9600
O1—H1	0.79 (5)	C32—H32C	0.9600
O2—C24	1.343 (8)	C28—C27	1.502 (6)
O2—H2	0.8200	C28—H28A	0.9600
O3—N4	1.222 (6)	C28—H28B	0.9600
O4—N4	1.244 (6)	C28—H28C	0.9600
N4—C19	1.433 (7)	C29—C30	1.500 (6)
C19—C20	1.405 (7)	C29—H29A	0.9600
C19—C24	1.428 (8)	C29—H29B	0.9600
C20—C21	1.388 (8)	C29—H29C	0.9600
C22—C21	1.362 (10)	C25—C26	1.497 (6)
C22—C23	1.375 (10)	C25—H25A	0.9600
C22—H22	0.9300	C25—H25B	0.9600
C21—H21	0.9300	C25—H25C	0.9600
C23—C24	1.376 (9)	C31—C30	1.400 (6)
C23—H23	0.9300	C27—C26	1.400 (6)
O5—C2	1.340 (5)	N8—C35	1.338 (6)
O5—H5	1.04 (6)	N8—C38	1.346 (6)
O6—C6	1.355 (5)	N7—C34	1.340 (6)
O6—H6	0.78 (5)	N7—C39	1.343 (6)
O8—N3	1.219 (5)	C37—C38	1.499 (6)
O7—N3	1.224 (5)	C37—H37A	0.9600
N3—C1	1.465 (5)	C37—H37B	0.9600
C3—C2	1.384 (6)	C37—H37C	0.9600
C3—C4	1.384 (6)	C36—C35	1.501 (6)
C3—H3	0.9300	C36—H36A	0.9600
C2—C1	1.402 (6)	C36—H36B	0.9600
C6—C5	1.387 (6)	C36—H36C	0.9600
C6—C1	1.388 (6)	C33—C34	1.496 (6)
C5—C4	1.389 (7)	C33—H33A	0.9600
C5—H5A	0.9300	C33—H33B	0.9600
C4—H4	0.9300	C33—H33C	0.9600
O10—C18	1.343 (6)	C38—C39	1.396 (6)
O10—H10A	0.80 (7)	C34—C35	1.399 (6)
O12—N1	1.236 (6)	C39—C40	1.504 (6)
O11—N1	1.236 (6)	C40—H40A	0.9600
O9—C14	1.344 (6)	C40—H40B	0.9600
O9—H9A	0.8200	C40—H40C	0.9600
C12—O13—H13	108 (4)	C14—C13—N1	119.4 (5)
C8—O14—H14	113 (4)	C18—C13—N1	119.5 (5)
O15—N2—O16	123.4 (4)	C18—C17—C16	119.7 (5)
O15—N2—C7	118.5 (4)	C18—C17—H17	120.1
O16—N2—C7	118.1 (4)	C16—C17—H17	120.1
O13—C12—C7	118.0 (4)	O9—C14—C15	116.6 (5)
O13—C12—C11	124.1 (4)	O9—C14—C13	124.9 (6)
C7—C12—C11	117.9 (4)	C15—C14—C13	118.5 (5)
O14—C8—C7	117.0 (4)	C26—N5—C31	119.5 (4)
O14—C8—C9	125.3 (4)	C27—N6—C30	119.4 (4)
C7—C8—C9	117.7 (4)	C31—C32—H32A	109.5
C10—C9—C8	118.8 (4)	C31—C32—H32B	109.5
C10—C9—H9	120.6	H32A—C32—H32B	109.5
C8—C9—H9	120.6	C31—C32—H32C	109.5
C12—C7—C8	123.4 (4)	H32A—C32—H32C	109.5
C12—C7—N2	119.0 (4)	H32B—C32—H32C	109.5
C8—C7—N2	117.6 (4)	C27—C28—H28A	109.5
C10—C11—C12	119.3 (4)	C27—C28—H28B	109.5
C10—C11—H11	120.3	H28A—C28—H28B	109.5
C12—C11—H11	120.3	C27—C28—H28C	109.5
C9—C10—C11	122.9 (4)	H28A—C28—H28C	109.5
C9—C10—H10	118.6	H28B—C28—H28C	109.5
C11—C10—H10	118.6	C30—C29—H29A	109.5
C20—O1—H1	106 (4)	C30—C29—H29B	109.5
C24—O2—H2	109.5	H29A—C29—H29B	109.5
O3—N4—O4	120.1 (5)	C30—C29—H29C	109.5
O3—N4—C19	120.5 (5)	H29A—C29—H29C	109.5
O4—N4—C19	119.4 (5)	H29B—C29—H29C	109.5
C20—C19—C24	119.9 (5)	C26—C25—H25A	109.5
C20—C19—N4	120.3 (5)	C26—C25—H25B	109.5
C24—C19—N4	119.7 (5)	H25A—C25—H25B	109.5
O1—C20—C21	116.8 (6)	C26—C25—H25C	109.5
O1—C20—C19	124.0 (5)	H25A—C25—H25C	109.5
C21—C20—C19	119.2 (6)	H25B—C25—H25C	109.5
C21—C22—C23	123.4 (6)	N5—C31—C30	120.2 (4)
C21—C22—H22	118.3	N5—C31—C32	117.9 (4)
C23—C22—H22	118.3	C30—C31—C32	121.9 (4)
C22—C21—C20	119.3 (6)	N6—C27—C26	120.4 (4)
C22—C21—H21	120.4	N6—C27—C28	118.0 (4)
C20—C21—H21	120.4	C26—C27—C28	121.6 (4)
C22—C23—C24	119.1 (7)	N5—C26—C27	120.3 (4)
C22—C23—H23	120.5	N5—C26—C25	117.3 (4)
C24—C23—H23	120.5	C27—C26—C25	122.4 (4)
O2—C24—C23	117.1 (6)	N6—C30—C31	120.1 (4)
O2—C24—C19	123.8 (6)	N6—C30—C29	117.3 (4)
C23—C24—C19	119.1 (6)	C31—C30—C29	122.6 (4)
C2—O5—H5	111 (3)	C35—N8—C38	119.8 (4)
C6—O6—H6	111 (4)	C34—N7—C39	119.1 (4)
O8—N3—O7	123.5 (4)	C38—C37—H37A	109.5
O8—N3—C1	118.8 (4)	C38—C37—H37B	109.5
O7—N3—C1	117.7 (4)	H37A—C37—H37B	109.5
C2—C3—C4	120.3 (4)	C38—C37—H37C	109.5
C2—C3—H3	119.8	H37A—C37—H37C	109.5
C4—C3—H3	119.8	H37B—C37—H37C	109.5
O5—C2—C3	125.0 (4)	C35—C36—H36A	109.5
O5—C2—C1	117.6 (4)	C35—C36—H36B	109.5
C3—C2—C1	117.4 (4)	H36A—C36—H36B	109.5
O6—C6—C5	123.6 (4)	C35—C36—H36C	109.5
O6—C6—C1	118.1 (4)	H36A—C36—H36C	109.5
C5—C6—C1	118.3 (4)	H36B—C36—H36C	109.5
C6—C1—C2	123.0 (4)	C34—C33—H33A	109.5
C6—C1—N3	118.0 (4)	C34—C33—H33B	109.5
C2—C1—N3	119.0 (4)	H33A—C33—H33B	109.5
C6—C5—C4	119.5 (4)	C34—C33—H33C	109.5
C6—C5—H5A	120.3	H33A—C33—H33C	109.5
C4—C5—H5A	120.3	H33B—C33—H33C	109.5
C3—C4—C5	121.5 (4)	N8—C38—C39	119.7 (4)
C3—C4—H4	119.2	N8—C38—C37	117.8 (4)
C5—C4—H4	119.2	C39—C38—C37	122.5 (4)
C18—O10—H10A	112 (5)	N7—C34—C35	120.6 (4)
C14—O9—H9A	109.5	N7—C34—C33	117.0 (4)
O12—N1—O11	120.2 (5)	C35—C34—C33	122.5 (4)
O12—N1—C13	119.7 (5)	N8—C35—C34	120.1 (4)
O11—N1—C13	120.1 (5)	N8—C35—C36	117.5 (4)
C16—C15—C14	120.8 (5)	C34—C35—C36	122.4 (4)
C16—C15—H15	119.6	N7—C39—C38	120.8 (4)
C14—C15—H15	119.6	N7—C39—C40	117.3 (4)
C15—C16—C17	121.2 (5)	C38—C39—C40	121.9 (4)
C15—C16—H16	119.4	C39—C40—H40A	109.5
C17—C16—H16	119.4	C39—C40—H40B	109.5
O10—C18—C17	116.3 (5)	H40A—C40—H40B	109.5
O10—C18—C13	125.0 (5)	C39—C40—H40C	109.5
C17—C18—C13	118.7 (5)	H40A—C40—H40C	109.5
C14—C13—C18	121.1 (5)	H40B—C40—H40C	109.5
O14—C8—C9—C10	179.9 (4)	C2—C3—C4—C5	−0.3 (7)
C7—C8—C9—C10	0.1 (6)	C6—C5—C4—C3	0.1 (7)
O13—C12—C7—C8	−179.3 (4)	C14—C15—C16—C17	0.1 (8)
C11—C12—C7—C8	−1.9 (7)	O10—C18—C13—C14	−178.2 (4)
O13—C12—C7—N2	1.2 (6)	C17—C18—C13—C14	0.8 (7)
C11—C12—C7—N2	178.6 (4)	O10—C18—C13—N1	1.3 (7)
O14—C8—C7—C12	−178.8 (4)	C17—C18—C13—N1	−179.7 (4)
C9—C8—C7—C12	1.1 (7)	O12—N1—C13—C14	−172.9 (5)
O14—C8—C7—N2	0.7 (6)	O11—N1—C13—C14	6.8 (7)
C9—C8—C7—N2	−179.5 (4)	O12—N1—C13—C18	7.6 (7)
O15—N2—C7—C12	−110.4 (5)	O11—N1—C13—C18	−172.7 (5)
O16—N2—C7—C12	67.3 (6)	O10—C18—C17—C16	179.4 (5)
O15—N2—C7—C8	70.1 (5)	C13—C18—C17—C16	0.3 (7)
O16—N2—C7—C8	−112.2 (5)	C15—C16—C17—C18	−0.8 (7)
O13—C12—C11—C10	178.9 (4)	C16—C15—C14—O9	−179.2 (5)
C7—C12—C11—C10	1.6 (7)	C16—C15—C14—C13	1.0 (7)
C8—C9—C10—C11	−0.3 (7)	C18—C13—C14—O9	178.7 (4)
C12—C11—C10—C9	−0.6 (7)	N1—C13—C14—O9	−0.8 (7)
O3—N4—C19—C20	5.3 (7)	C18—C13—C14—C15	−1.5 (7)
O4—N4—C19—C20	−175.0 (5)	N1—C13—C14—C15	179.0 (5)
O3—N4—C19—C24	−172.7 (4)	C26—N5—C31—C30	−1.9 (6)
O4—N4—C19—C24	6.9 (7)	C26—N5—C31—C32	178.3 (4)
C24—C19—C20—O1	−179.8 (5)	C30—N6—C27—C26	−0.3 (6)
N4—C19—C20—O1	2.1 (7)	C30—N6—C27—C28	179.4 (4)
C24—C19—C20—C21	0.1 (7)	C31—N5—C26—C27	1.7 (6)
N4—C19—C20—C21	−177.9 (5)	C31—N5—C26—C25	−178.6 (4)
C23—C22—C21—C20	−0.4 (9)	N6—C27—C26—N5	−0.6 (6)
O1—C20—C21—C22	−179.9 (5)	C28—C27—C26—N5	179.7 (4)
C19—C20—C21—C22	0.1 (8)	N6—C27—C26—C25	179.8 (4)
C21—C22—C23—C24	0.4 (9)	C28—C27—C26—C25	0.1 (7)
C22—C23—C24—O2	178.8 (5)	C27—N6—C30—C31	0.0 (6)
C22—C23—C24—C19	−0.2 (8)	C27—N6—C30—C29	−179.8 (4)
C20—C19—C24—O2	−179.0 (5)	N5—C31—C30—N6	1.1 (6)
N4—C19—C24—O2	−1.0 (7)	C32—C31—C30—N6	−179.2 (4)
C20—C19—C24—C23	−0.1 (8)	N5—C31—C30—C29	−179.1 (4)
N4—C19—C24—C23	178.0 (5)	C32—C31—C30—C29	0.7 (7)
C4—C3—C2—O5	−177.8 (4)	C35—N8—C38—C39	−1.3 (6)
C4—C3—C2—C1	0.4 (6)	C35—N8—C38—C37	179.6 (4)
O6—C6—C1—C2	179.0 (4)	C39—N7—C34—C35	−1.5 (6)
C5—C6—C1—C2	0.1 (7)	C39—N7—C34—C33	177.7 (4)
O6—C6—C1—N3	0.1 (6)	C38—N8—C35—C34	0.6 (6)
C5—C6—C1—N3	−178.9 (4)	C38—N8—C35—C36	−178.5 (4)
O5—C2—C1—C6	178.1 (4)	N7—C34—C35—N8	0.8 (6)
C3—C2—C1—C6	−0.3 (6)	C33—C34—C35—N8	−178.4 (4)
O5—C2—C1—N3	−3.0 (6)	N7—C34—C35—C36	179.9 (4)
C3—C2—C1—N3	178.6 (4)	C33—C34—C35—C36	0.7 (7)
O8—N3—C1—C6	110.2 (5)	C34—N7—C39—C38	0.9 (6)
O7—N3—C1—C6	−68.9 (5)	C34—N7—C39—C40	−178.3 (4)
O8—N3—C1—C2	−68.8 (5)	N8—C38—C39—N7	0.5 (6)
O7—N3—C1—C2	112.1 (5)	C37—C38—C39—N7	179.6 (4)
O6—C6—C5—C4	−178.9 (4)	N8—C38—C39—C40	179.7 (4)
C1—C6—C5—C4	0.0 (7)	C37—C38—C39—C40	−1.2 (7)

(2NRES-TMP)

Crystal data

C6H5NO4·1.5(C8H12N2)	Z = 2
Mr = 359.40	F(000) = 382
Triclinic, P1	Dx = 1.246 Mg m^−3
a = 7.658 (2) Å	Mo Kα radiation, λ = 0.71075 Å
b = 9.277 (3) Å	Cell parameters from 5527 reflections
c = 15.152 (5) Å	θ = 3.0–27.7°
α = 79.304 (6)°	µ = 0.09 mm^−1
β = 82.008 (6)°	T = 150 K
γ = 65.214 (5)°	Block, yellow
V = 957.9 (5) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	1894 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.059
profile data from ω–scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.683, Tmax = 1.000	k = −11→11
6882 measured reflections	l = −18→18
3305 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.078	w = 1/[σ^2(Fo^2) + (0.122P)^2 + 0.3342P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.253	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.27 e Å^−3
3305 reflections	Δρmin = −0.25 e Å^−3
247 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.020 (8)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O2	0.0736 (4)	0.6091 (4)	0.6982 (2)	0.0558 (9)
H2	0.063749	0.694471	0.667492	0.084*
O1	0.4591 (5)	0.1968 (4)	0.9072 (2)	0.0594 (10)
N1	0.8110 (5)	0.0571 (4)	0.9808 (2)	0.0460 (10)
N2	0.0330 (5)	0.8706 (4)	0.5667 (2)	0.0417 (9)
N4	0.1161 (5)	0.3582 (4)	0.8311 (3)	0.0454 (9)
O4	−0.0012 (6)	0.4247 (5)	0.8885 (3)	0.0847 (13)
N3	0.4585 (5)	0.1495 (4)	0.4485 (3)	0.0499 (10)
C2	0.2505 (6)	0.5352 (5)	0.7326 (3)	0.0396 (10)
C6	0.4516 (6)	0.3189 (5)	0.8416 (3)	0.0413 (10)
C12	0.0183 (5)	0.8559 (5)	0.4815 (3)	0.0382 (10)
C1	0.2772 (6)	0.4050 (5)	0.8002 (2)	0.0374 (10)
C13	0.0167 (6)	1.0116 (5)	0.5863 (3)	0.0404 (10)
C16	0.4877 (6)	0.1261 (5)	0.5365 (3)	0.0449 (11)
C17	0.4700 (6)	0.0246 (5)	0.4112 (3)	0.0453 (11)
C3	0.4047 (6)	0.5778 (5)	0.7036 (3)	0.0449 (11)
H3	0.391161	0.663619	0.658206	0.054*
C8	0.9390 (6)	−0.0818 (5)	0.9550 (3)	0.0444 (11)
O3	0.1069 (6)	0.2522 (6)	0.7987 (3)	0.1051 (16)
C5	0.6034 (6)	0.3644 (5)	0.8106 (3)	0.0487 (11)
H5	0.721908	0.308864	0.835766	0.058*
C9	0.8692 (6)	0.1410 (5)	1.0252 (3)	0.0466 (11)
C4	0.5787 (6)	0.4918 (5)	0.7427 (3)	0.0502 (12)
H4	0.681737	0.520521	0.722736	0.060*
C7	0.8639 (8)	−0.1719 (6)	0.9075 (3)	0.0601 (13)
H7A	0.868205	−0.267750	0.946088	0.090*
H7B	0.942536	−0.199802	0.853017	0.090*
H7C	0.733239	−0.105245	0.893241	0.090*
C14	0.0339 (8)	1.0218 (6)	0.6825 (3)	0.0583 (13)
H14A	−0.088596	1.091322	0.707349	0.087*
H14B	0.128155	1.063902	0.684649	0.087*
H14C	0.073084	0.916779	0.716990	0.087*
C11	0.0387 (7)	0.6950 (5)	0.4640 (3)	0.0583 (13)
H11A	0.168328	0.636130	0.441392	0.087*
H11B	−0.049326	0.709853	0.420406	0.087*
H11C	0.010015	0.636255	0.519075	0.087*
C18	0.4373 (8)	0.0547 (7)	0.3141 (3)	0.0669 (14)
H18A	0.316031	0.052284	0.306902	0.100*
H18B	0.539209	−0.026601	0.283964	0.100*
H18C	0.435495	0.158060	0.288469	0.100*
C10	0.7187 (7)	0.2954 (6)	1.0520 (4)	0.0674 (15)
H10A	0.598738	0.317296	1.028405	0.101*
H10B	0.758625	0.381131	1.028407	0.101*
H10C	0.702353	0.286712	1.116517	0.101*
C15	0.4711 (8)	0.2696 (6)	0.5761 (4)	0.0678 (15)
H15A	0.464801	0.355521	0.528504	0.102*
H15B	0.581634	0.240866	0.609411	0.102*
H15C	0.356311	0.303708	0.615612	0.102*
H1	0.568 (11)	0.138 (9)	0.920 (5)	0.12 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0542 (19)	0.0488 (19)	0.058 (2)	−0.0181 (16)	−0.0192 (15)	0.0132 (15)
O1	0.047 (2)	0.057 (2)	0.065 (2)	−0.0204 (17)	−0.0196 (16)	0.0234 (17)
N1	0.045 (2)	0.042 (2)	0.041 (2)	−0.0081 (18)	−0.0099 (16)	0.0015 (16)
N2	0.044 (2)	0.034 (2)	0.041 (2)	−0.0117 (16)	−0.0088 (15)	0.0013 (15)
N4	0.040 (2)	0.039 (2)	0.057 (2)	−0.0149 (18)	−0.0116 (18)	−0.0026 (17)
O4	0.078 (3)	0.089 (3)	0.097 (3)	−0.048 (2)	0.038 (2)	−0.035 (2)
N3	0.048 (2)	0.046 (2)	0.056 (2)	−0.0190 (19)	−0.0014 (18)	−0.0108 (18)
C2	0.046 (2)	0.034 (2)	0.036 (2)	−0.012 (2)	−0.0081 (18)	−0.0050 (17)
C6	0.040 (2)	0.042 (2)	0.038 (2)	−0.013 (2)	−0.0095 (18)	0.0004 (18)
C12	0.033 (2)	0.035 (2)	0.044 (2)	−0.0104 (18)	−0.0065 (17)	−0.0036 (17)
C1	0.038 (2)	0.038 (2)	0.036 (2)	−0.0160 (19)	−0.0020 (17)	−0.0038 (17)
C13	0.035 (2)	0.040 (2)	0.043 (2)	−0.0121 (19)	−0.0055 (18)	−0.0034 (18)
C16	0.039 (2)	0.045 (3)	0.055 (3)	−0.019 (2)	0.004 (2)	−0.020 (2)
C17	0.042 (2)	0.050 (3)	0.048 (3)	−0.021 (2)	−0.0012 (19)	−0.013 (2)
C3	0.052 (3)	0.040 (2)	0.043 (2)	−0.021 (2)	0.000 (2)	−0.0038 (19)
C8	0.051 (3)	0.043 (2)	0.034 (2)	−0.014 (2)	−0.0093 (19)	0.0013 (18)
O3	0.092 (3)	0.124 (4)	0.145 (4)	−0.075 (3)	0.022 (3)	−0.072 (3)
C5	0.036 (2)	0.055 (3)	0.054 (3)	−0.017 (2)	−0.009 (2)	−0.004 (2)
C9	0.053 (3)	0.041 (2)	0.036 (2)	−0.009 (2)	−0.007 (2)	−0.0026 (18)
C4	0.044 (3)	0.048 (3)	0.063 (3)	−0.024 (2)	0.007 (2)	−0.012 (2)
C7	0.076 (3)	0.057 (3)	0.047 (3)	−0.024 (3)	−0.016 (2)	−0.007 (2)
C14	0.075 (3)	0.058 (3)	0.045 (3)	−0.027 (3)	−0.017 (2)	−0.004 (2)
C11	0.066 (3)	0.044 (3)	0.070 (3)	−0.024 (2)	−0.010 (3)	−0.013 (2)
C18	0.070 (3)	0.084 (4)	0.054 (3)	−0.036 (3)	−0.013 (3)	−0.009 (3)
C10	0.063 (3)	0.051 (3)	0.072 (3)	−0.002 (3)	−0.006 (3)	−0.017 (2)
C15	0.069 (3)	0.055 (3)	0.082 (4)	−0.020 (3)	−0.006 (3)	−0.027 (3)

Geometric parameters (Å, º)

O2—C2	1.365 (5)	C8—C9^iii	1.390 (6)
O2—H2	0.8200	C8—C7	1.513 (6)
O1—C6	1.348 (5)	C5—C4	1.380 (6)
O1—H1	0.81 (7)	C5—H5	0.9300
N1—C8	1.340 (5)	C9—C10	1.499 (6)
N1—C9	1.352 (6)	C4—H4	0.9300
N2—C13	1.346 (5)	C7—H7A	0.9600
N2—C12	1.347 (5)	C7—H7B	0.9600
N4—O3	1.207 (5)	C7—H7C	0.9600
N4—O4	1.209 (5)	C14—H14A	0.9600
N4—C1	1.464 (5)	C14—H14B	0.9600
N3—C16	1.344 (5)	C14—H14C	0.9600
N3—C17	1.347 (5)	C11—H11A	0.9600
C2—C3	1.388 (6)	C11—H11B	0.9600
C2—C1	1.393 (5)	C11—H11C	0.9600
C6—C5	1.391 (6)	C18—H18A	0.9600
C6—C1	1.402 (5)	C18—H18B	0.9600
C12—C13^i	1.404 (6)	C18—H18C	0.9600
C12—C11	1.504 (6)	C10—H10A	0.9600
C13—C14	1.506 (6)	C10—H10B	0.9600
C16—C17^ii	1.404 (6)	C10—H10C	0.9600
C16—C15	1.511 (6)	C15—H15A	0.9600
C17—C18	1.482 (6)	C15—H15B	0.9600
C3—C4	1.385 (6)	C15—H15C	0.9600
C3—H3	0.9300
C2—O2—H2	109.5	C8^iii—C9—C10	123.1 (4)
C6—O1—H1	113 (5)	C5—C4—C3	121.7 (4)
C8—N1—C9	119.8 (4)	C5—C4—H4	119.1
C13—N2—C12	120.0 (3)	C3—C4—H4	119.1
O3—N4—O4	122.3 (4)	C8—C7—H7A	109.5
O3—N4—C1	118.3 (4)	C8—C7—H7B	109.5
O4—N4—C1	119.3 (4)	H7A—C7—H7B	109.5
C16—N3—C17	118.6 (4)	C8—C7—H7C	109.5
O2—C2—C3	124.8 (3)	H7A—C7—H7C	109.5
O2—C2—C1	116.7 (4)	H7B—C7—H7C	109.5
C3—C2—C1	118.4 (4)	C13—C14—H14A	109.5
O1—C6—C5	125.4 (4)	C13—C14—H14B	109.5
O1—C6—C1	117.1 (4)	H14A—C14—H14B	109.5
C5—C6—C1	117.5 (4)	C13—C14—H14C	109.5
N2—C12—C13^i	119.8 (4)	H14A—C14—H14C	109.5
N2—C12—C11	117.3 (4)	H14B—C14—H14C	109.5
C13^i—C12—C11	122.9 (4)	C12—C11—H11A	109.5
C2—C1—C6	122.5 (4)	C12—C11—H11B	109.5
C2—C1—N4	119.0 (3)	H11A—C11—H11B	109.5
C6—C1—N4	118.5 (3)	C12—C11—H11C	109.5
N2—C13—C12^i	120.2 (4)	H11A—C11—H11C	109.5
N2—C13—C14	117.9 (3)	H11B—C11—H11C	109.5
C12^i—C13—C14	121.9 (4)	C17—C18—H18A	109.5
N3—C16—C17^ii	121.3 (4)	C17—C18—H18B	109.5
N3—C16—C15	116.9 (4)	H18A—C18—H18B	109.5
C17^ii—C16—C15	121.8 (4)	C17—C18—H18C	109.5
N3—C17—C16^ii	120.2 (4)	H18A—C18—H18C	109.5
N3—C17—C18	117.1 (4)	H18B—C18—H18C	109.5
C16^ii—C17—C18	122.7 (4)	C9—C10—H10A	109.5
C4—C3—C2	119.6 (4)	C9—C10—H10B	109.5
C4—C3—H3	120.2	H10A—C10—H10B	109.5
C2—C3—H3	120.2	C9—C10—H10C	109.5
N1—C8—C9^iii	120.3 (4)	H10A—C10—H10C	109.5
N1—C8—C7	117.2 (4)	H10B—C10—H10C	109.5
C9^iii—C8—C7	122.4 (4)	C16—C15—H15A	109.5
C4—C5—C6	120.2 (4)	C16—C15—H15B	109.5
C4—C5—H5	119.9	H15A—C15—H15B	109.5
C6—C5—H5	119.9	C16—C15—H15C	109.5
N1—C9—C8^iii	119.9 (4)	H15A—C15—H15C	109.5
N1—C9—C10	117.1 (4)	H15B—C15—H15C	109.5
C13—N2—C12—C13^i	−0.9 (6)	C12—N2—C13—C14	179.9 (4)
C13—N2—C12—C11	179.7 (4)	C17—N3—C16—C17^ii	0.2 (7)
O2—C2—C1—C6	−179.8 (4)	C17—N3—C16—C15	−179.3 (4)
C3—C2—C1—C6	2.0 (6)	C16—N3—C17—C16^ii	−0.2 (7)
O2—C2—C1—N4	−1.4 (6)	C16—N3—C17—C18	−179.9 (4)
C3—C2—C1—N4	−179.6 (4)	O2—C2—C3—C4	−178.8 (4)
O1—C6—C1—C2	178.9 (4)	C1—C2—C3—C4	−0.6 (6)
C5—C6—C1—C2	−2.2 (6)	C9—N1—C8—C9^iii	0.8 (6)
O1—C6—C1—N4	0.5 (6)	C9—N1—C8—C7	178.6 (4)
C5—C6—C1—N4	179.4 (4)	O1—C6—C5—C4	179.9 (4)
O3—N4—C1—C2	96.0 (5)	C1—C6—C5—C4	1.1 (6)
O4—N4—C1—C2	−85.0 (5)	C8—N1—C9—C8^iii	−0.8 (6)
O3—N4—C1—C6	−85.6 (5)	C8—N1—C9—C10	180.0 (4)
O4—N4—C1—C6	93.5 (5)	C6—C5—C4—C3	0.1 (7)
C12—N2—C13—C12^i	0.9 (6)	C2—C3—C4—C5	−0.4 (7)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+2, −y, −z+2.

(3NRES-ACR)

Crystal data

C32H23N3O3.99	Z = 4
Mr = 513.33	F(000) = 1072
Triclinic, P1	Dx = 1.370 Mg m^−3
a = 9.2447 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.4694 (13) Å	Cell parameters from 20527 reflections
c = 19.3202 (18) Å	θ = 3.0–27.6°
α = 93.232 (7)°	µ = 0.09 mm^−1
β = 102.634 (7)°	T = 150 K
γ = 97.795 (7)°	Block, yellow
V = 2488.6 (4) Å^3	0.29 × 0.22 × 0.17 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	7523 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.045
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −11→12
Tmin = 0.762, Tmax = 1.000	k = −18→18
25721 measured reflections	l = −24→25
11355 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.159	w = 1/[σ^2(Fo^2) + (0.0665P)^2 + 0.7465P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
11355 reflections	Δρmax = 0.58 e Å^−3
729 parameters	Δρmin = −0.40 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	1.02767 (19)	0.09475 (10)	0.43919 (8)	0.0241 (4)
C40	0.8842 (2)	0.11091 (13)	0.42520 (10)	0.0249 (4)
C41	0.7959 (3)	0.09336 (15)	0.35405 (11)	0.0346 (5)
H41	0.838130	0.071641	0.317946	0.041*
C42	0.6510 (3)	0.10808 (16)	0.33857 (13)	0.0426 (6)
H42	0.594862	0.096223	0.291924	0.051*
C43	0.5838 (3)	0.14139 (16)	0.39269 (14)	0.0428 (6)
H43	0.484524	0.151522	0.381117	0.051*
C44	0.6635 (2)	0.15847 (14)	0.46098 (12)	0.0346 (5)
H44	0.617995	0.179719	0.495980	0.042*
C45	0.8163 (2)	0.14427 (13)	0.47990 (11)	0.0260 (4)
C46	0.9031 (2)	0.16090 (13)	0.54892 (10)	0.0254 (4)
H46	0.861547	0.181898	0.585491	0.031*
C47	1.0527 (2)	0.14621 (12)	0.56374 (10)	0.0232 (4)
C48	1.1477 (2)	0.16304 (14)	0.63360 (10)	0.0297 (5)
H48	1.110734	0.185029	0.671451	0.036*
C49	1.2923 (3)	0.14686 (15)	0.64478 (11)	0.0336 (5)
H49	1.353879	0.158372	0.690342	0.040*
C50	1.3504 (2)	0.11272 (14)	0.58791 (11)	0.0322 (5)
H50	1.449253	0.101702	0.596708	0.039*
C51	1.2635 (2)	0.09588 (13)	0.52075 (11)	0.0275 (4)
H51	1.303298	0.073511	0.483994	0.033*
C52	1.1117 (2)	0.11231 (12)	0.50630 (10)	0.0227 (4)
N2	0.48018 (18)	0.41106 (10)	0.42076 (8)	0.0223 (3)
C27	0.2460 (2)	0.41349 (14)	0.33878 (11)	0.0304 (5)
H27	0.296503	0.437734	0.305578	0.037*
C28	0.0938 (3)	0.39716 (16)	0.32272 (12)	0.0389 (5)
H28	0.041158	0.410527	0.278555	0.047*
C29	0.0137 (3)	0.35985 (15)	0.37253 (13)	0.0382 (5)
H29	−0.090588	0.348414	0.360555	0.046*
C30	0.0887 (2)	0.34108 (14)	0.43700 (12)	0.0316 (5)
H30	0.035230	0.317468	0.469341	0.038*
C31	0.2486 (2)	0.35680 (13)	0.45651 (10)	0.0244 (4)
C32	0.3311 (2)	0.33894 (13)	0.52234 (10)	0.0253 (4)
H32	0.281716	0.316303	0.556418	0.030*
C33	0.4875 (2)	0.35472 (12)	0.53763 (10)	0.0223 (4)
C34	0.5787 (2)	0.33647 (14)	0.60361 (10)	0.0293 (5)
H34	0.533717	0.313136	0.638937	0.035*
C35	0.7306 (2)	0.35284 (14)	0.61534 (11)	0.0315 (5)
H35	0.788768	0.340183	0.658457	0.038*
C36	0.8013 (2)	0.38928 (13)	0.56201 (11)	0.0293 (5)
H36	0.905446	0.400151	0.570719	0.035*
C37	0.7189 (2)	0.40834 (13)	0.49872 (10)	0.0257 (4)
H37	0.766997	0.432658	0.464696	0.031*
C38	0.5595 (2)	0.39142 (12)	0.48398 (10)	0.0210 (4)
C39	0.3287 (2)	0.39374 (13)	0.40614 (10)	0.0234 (4)
C20	0.4392 (2)	0.83894 (13)	0.06174 (10)	0.0263 (4)
H20	0.395732	0.815663	0.097540	0.032*
C14	0.5947 (2)	0.86094 (13)	0.07412 (10)	0.0251 (4)
C15	0.6928 (3)	0.85036 (14)	0.13999 (11)	0.0329 (5)
H15	0.653314	0.828299	0.177326	0.040*
C16	0.8440 (3)	0.87223 (15)	0.14890 (12)	0.0372 (5)
H16	0.907172	0.865628	0.192372	0.045*
C17	0.9055 (3)	0.90497 (14)	0.09224 (12)	0.0352 (5)
H17	1.009106	0.918499	0.098739	0.042*
C18	0.8162 (2)	0.91702 (13)	0.02857 (11)	0.0300 (5)
H18	0.858966	0.939215	−0.007771	0.036*
C19	0.6569 (2)	0.89577 (12)	0.01715 (10)	0.0233 (4)
N3	0.57066 (19)	0.90952 (10)	−0.04613 (8)	0.0238 (4)
C21	0.4200 (2)	0.88807 (12)	−0.05718 (10)	0.0233 (4)
C22	0.3286 (2)	0.90207 (13)	−0.12401 (10)	0.0290 (5)
H22	0.372767	0.926544	−0.159229	0.035*
C23	0.1772 (3)	0.87994 (14)	−0.13671 (12)	0.0355 (5)
H23	0.118821	0.888921	−0.180837	0.043*
C24	0.1063 (3)	0.84330 (15)	−0.08377 (13)	0.0377 (5)
H24	0.002423	0.827899	−0.093720	0.045*
C25	0.1887 (2)	0.83067 (13)	−0.01910 (12)	0.0316 (5)
H25	0.140946	0.808273	0.015597	0.038*
C26	0.3487 (2)	0.85138 (12)	−0.00342 (10)	0.0239 (4)
C7	0.0092 (2)	0.66044 (13)	0.08920 (10)	0.0264 (4)
H7	−0.021595	0.681285	0.129285	0.032*
C1	0.1535 (2)	0.63897 (13)	0.09619 (10)	0.0255 (4)
C2	0.2603 (3)	0.64742 (14)	0.16295 (11)	0.0318 (5)
H2	0.234109	0.668352	0.204270	0.038*
C3	0.4002 (3)	0.62507 (15)	0.16655 (12)	0.0349 (5)
H3	0.468324	0.630023	0.210332	0.042*
C4	0.4423 (3)	0.59434 (15)	0.10392 (12)	0.0347 (5)
H4	0.538578	0.580251	0.106995	0.042*
C5	0.3440 (2)	0.58507 (13)	0.03918 (11)	0.0294 (5)
H5	0.373774	0.564671	−0.001303	0.035*
C6	0.1963 (2)	0.60636 (12)	0.03313 (10)	0.0236 (4)
N4	0.10118 (19)	0.59591 (10)	−0.03158 (8)	0.0245 (4)
C8	−0.0382 (2)	0.61774 (13)	−0.03747 (10)	0.0251 (4)
C9	−0.1382 (2)	0.60792 (14)	−0.10569 (11)	0.0305 (5)
H9	−0.106934	0.586500	−0.145464	0.037*
C10	−0.2794 (3)	0.62957 (14)	−0.11335 (12)	0.0343 (5)
H10	−0.343385	0.622831	−0.158347	0.041*
C11	−0.3302 (3)	0.66231 (14)	−0.05352 (13)	0.0360 (5)
H11	−0.426623	0.677262	−0.059638	0.043*
C12	−0.2386 (2)	0.67184 (14)	0.01249 (12)	0.0312 (5)
H12	−0.273606	0.692196	0.051433	0.037*
C13	−0.0892 (2)	0.65104 (13)	0.02297 (10)	0.0250 (4)
O1	0.85130 (18)	0.49834 (9)	0.14411 (8)	0.0352 (4)
H1	0.857900	0.463880	0.110121	0.053*
O2	0.63299 (17)	0.51091 (9)	0.34051 (7)	0.0309 (3)
H2A	0.582844	0.479150	0.363210	0.046*
O5	0.9096 (2)	0.61645 (12)	0.31244 (10)	0.0618 (6)
O6	0.7650 (2)	0.65495 (10)	0.22096 (9)	0.0475 (4)
N6	0.80915 (18)	0.59709 (11)	0.25947 (8)	0.0232 (4)
C53	0.7414 (2)	0.49862 (12)	0.24225 (9)	0.0194 (4)
C54	0.7690 (2)	0.44999 (13)	0.18366 (9)	0.0221 (4)
C55	0.7147 (2)	0.35471 (13)	0.17041 (10)	0.0262 (4)
H55	0.732634	0.320126	0.131934	0.031*
C56	0.6337 (2)	0.31216 (13)	0.21537 (10)	0.0270 (4)
H56	0.598597	0.248269	0.206826	0.032*
C57	0.6031 (2)	0.36130 (13)	0.27243 (10)	0.0258 (4)
H57	0.546180	0.330955	0.300969	0.031*
C58	0.6578 (2)	0.45657 (13)	0.28712 (9)	0.0215 (4)
O3	0.14648 (19)	−0.00245 (10)	0.35063 (7)	0.0354 (4)
H3A	0.106887	0.030186	0.374830	0.053*
O4	0.32772 (18)	−0.00928 (9)	0.14213 (7)	0.0328 (4)
H4A	0.355296	0.024294	0.113214	0.049*
N5	0.26203 (19)	−0.09878 (11)	0.25486 (9)	0.0246 (4)
C59	0.2409 (2)	−0.00080 (12)	0.24754 (9)	0.0200 (4)
C60	0.1845 (2)	0.04575 (13)	0.29861 (9)	0.0221 (4)
C61	0.1745 (2)	0.14063 (13)	0.29335 (10)	0.0256 (4)
H61	0.138329	0.173902	0.326814	0.031*
C62	0.2188 (2)	0.18499 (13)	0.23793 (10)	0.0273 (4)
H62	0.213193	0.248406	0.235151	0.033*
C63	0.2712 (2)	0.13734 (13)	0.18670 (10)	0.0253 (4)
H63	0.298389	0.168404	0.149563	0.030*
C64	0.2831 (2)	0.04297 (13)	0.19076 (9)	0.0216 (4)
O8	0.1573 (2)	−0.15747 (13)	0.25752 (16)	0.0356 (9)	0.770 (7)
O7	0.3913 (2)	−0.11700 (14)	0.26010 (18)	0.0427 (10)	0.800 (8)
O12	0.1801 (11)	−0.1557 (5)	0.2054 (6)	0.047 (4)	0.203 (8)
O11	0.3353 (15)	−0.1184 (6)	0.3042 (7)	0.058 (5)	0.202 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0306 (10)	0.0211 (8)	0.0224 (8)	0.0024 (7)	0.0106 (7)	0.0042 (6)
C40	0.0292 (11)	0.0195 (9)	0.0257 (10)	−0.0010 (8)	0.0077 (9)	0.0044 (8)
C41	0.0399 (13)	0.0348 (12)	0.0257 (11)	−0.0017 (10)	0.0042 (10)	0.0066 (9)
C42	0.0403 (14)	0.0416 (13)	0.0378 (13)	−0.0041 (11)	−0.0044 (11)	0.0132 (10)
C43	0.0279 (12)	0.0360 (13)	0.0609 (16)	0.0031 (10)	0.0018 (12)	0.0113 (11)
C44	0.0290 (12)	0.0274 (11)	0.0487 (14)	0.0036 (9)	0.0110 (11)	0.0074 (10)
C45	0.0277 (11)	0.0193 (10)	0.0329 (11)	0.0017 (8)	0.0107 (9)	0.0071 (8)
C46	0.0343 (12)	0.0182 (9)	0.0278 (10)	0.0041 (8)	0.0154 (9)	0.0034 (8)
C47	0.0312 (11)	0.0166 (9)	0.0234 (10)	0.0019 (8)	0.0102 (9)	0.0045 (7)
C48	0.0396 (13)	0.0267 (10)	0.0234 (10)	0.0035 (9)	0.0099 (9)	0.0016 (8)
C49	0.0366 (13)	0.0348 (12)	0.0264 (11)	0.0015 (10)	0.0015 (10)	0.0072 (9)
C50	0.0271 (11)	0.0286 (11)	0.0413 (12)	0.0044 (9)	0.0067 (10)	0.0107 (9)
C51	0.0297 (11)	0.0247 (10)	0.0316 (11)	0.0058 (8)	0.0127 (9)	0.0050 (8)
C52	0.0298 (11)	0.0156 (9)	0.0245 (10)	0.0015 (8)	0.0103 (9)	0.0043 (7)
N2	0.0263 (9)	0.0210 (8)	0.0216 (8)	0.0059 (7)	0.0088 (7)	−0.0005 (6)
C27	0.0361 (12)	0.0308 (11)	0.0241 (10)	0.0093 (9)	0.0047 (9)	−0.0014 (8)
C28	0.0381 (14)	0.0389 (13)	0.0345 (12)	0.0119 (10)	−0.0046 (11)	−0.0032 (10)
C29	0.0248 (12)	0.0357 (12)	0.0510 (14)	0.0067 (9)	0.0028 (11)	−0.0047 (10)
C30	0.0254 (11)	0.0252 (10)	0.0445 (13)	0.0029 (8)	0.0103 (10)	−0.0002 (9)
C31	0.0265 (11)	0.0176 (9)	0.0307 (10)	0.0035 (8)	0.0105 (9)	−0.0004 (8)
C32	0.0301 (11)	0.0202 (10)	0.0290 (10)	0.0028 (8)	0.0150 (9)	0.0019 (8)
C33	0.0294 (11)	0.0166 (9)	0.0224 (9)	0.0029 (8)	0.0098 (8)	0.0001 (7)
C34	0.0386 (13)	0.0265 (11)	0.0244 (10)	0.0053 (9)	0.0105 (9)	0.0031 (8)
C35	0.0351 (13)	0.0322 (11)	0.0245 (10)	0.0081 (9)	0.0001 (9)	−0.0010 (8)
C36	0.0248 (11)	0.0271 (11)	0.0349 (11)	0.0046 (8)	0.0055 (9)	−0.0037 (9)
C37	0.0260 (11)	0.0231 (10)	0.0291 (10)	0.0026 (8)	0.0102 (9)	−0.0003 (8)
C38	0.0259 (10)	0.0164 (9)	0.0220 (9)	0.0035 (7)	0.0088 (8)	−0.0017 (7)
C39	0.0278 (11)	0.0200 (9)	0.0233 (10)	0.0053 (8)	0.0077 (8)	−0.0011 (7)
C20	0.0386 (12)	0.0176 (9)	0.0294 (11)	0.0075 (8)	0.0189 (10)	0.0058 (8)
C14	0.0377 (12)	0.0181 (9)	0.0232 (10)	0.0080 (8)	0.0123 (9)	0.0016 (7)
C15	0.0476 (14)	0.0283 (11)	0.0263 (11)	0.0129 (10)	0.0103 (10)	0.0073 (8)
C16	0.0436 (14)	0.0349 (12)	0.0298 (11)	0.0100 (10)	−0.0012 (10)	0.0031 (9)
C17	0.0296 (12)	0.0295 (11)	0.0433 (13)	0.0057 (9)	0.0020 (10)	−0.0010 (9)
C18	0.0346 (12)	0.0222 (10)	0.0350 (11)	0.0026 (9)	0.0132 (10)	0.0006 (8)
C19	0.0323 (11)	0.0167 (9)	0.0231 (10)	0.0060 (8)	0.0099 (9)	0.0006 (7)
N3	0.0320 (10)	0.0198 (8)	0.0225 (8)	0.0052 (7)	0.0121 (7)	0.0010 (6)
C21	0.0330 (11)	0.0168 (9)	0.0227 (9)	0.0057 (8)	0.0108 (9)	−0.0004 (7)
C22	0.0397 (13)	0.0225 (10)	0.0252 (10)	0.0064 (9)	0.0077 (10)	0.0006 (8)
C23	0.0410 (14)	0.0278 (11)	0.0335 (12)	0.0083 (10)	−0.0015 (10)	0.0001 (9)
C24	0.0287 (12)	0.0284 (11)	0.0542 (15)	0.0045 (9)	0.0058 (11)	0.0023 (10)
C25	0.0333 (12)	0.0220 (10)	0.0440 (13)	0.0057 (9)	0.0171 (10)	0.0057 (9)
C26	0.0313 (11)	0.0156 (9)	0.0279 (10)	0.0052 (8)	0.0120 (9)	0.0026 (7)
C7	0.0388 (12)	0.0180 (9)	0.0265 (10)	0.0022 (8)	0.0177 (9)	0.0016 (7)
C1	0.0345 (12)	0.0183 (9)	0.0261 (10)	0.0025 (8)	0.0132 (9)	0.0032 (8)
C2	0.0443 (14)	0.0273 (11)	0.0251 (10)	0.0025 (9)	0.0126 (10)	0.0016 (8)
C3	0.0376 (13)	0.0345 (12)	0.0306 (11)	0.0043 (10)	0.0041 (10)	0.0047 (9)
C4	0.0347 (13)	0.0305 (11)	0.0406 (13)	0.0068 (9)	0.0100 (11)	0.0068 (9)
C5	0.0377 (12)	0.0236 (10)	0.0317 (11)	0.0057 (9)	0.0170 (10)	0.0052 (8)
C6	0.0320 (11)	0.0160 (9)	0.0251 (10)	0.0016 (8)	0.0123 (9)	0.0038 (7)
N4	0.0320 (10)	0.0194 (8)	0.0250 (8)	0.0033 (7)	0.0131 (8)	0.0036 (6)
C8	0.0329 (11)	0.0182 (9)	0.0266 (10)	0.0003 (8)	0.0132 (9)	0.0051 (7)
C9	0.0383 (13)	0.0272 (11)	0.0274 (11)	0.0009 (9)	0.0121 (10)	0.0057 (8)
C10	0.0370 (13)	0.0293 (11)	0.0335 (12)	0.0001 (9)	0.0037 (10)	0.0068 (9)
C11	0.0293 (12)	0.0267 (11)	0.0533 (14)	0.0045 (9)	0.0114 (11)	0.0062 (10)
C12	0.0345 (12)	0.0226 (10)	0.0399 (12)	0.0028 (9)	0.0171 (10)	0.0011 (9)
C13	0.0299 (11)	0.0173 (9)	0.0305 (10)	0.0013 (8)	0.0140 (9)	0.0029 (8)
O1	0.0527 (10)	0.0264 (8)	0.0320 (8)	−0.0033 (7)	0.0285 (8)	−0.0036 (6)
O2	0.0443 (9)	0.0262 (7)	0.0269 (7)	0.0019 (6)	0.0213 (7)	−0.0011 (6)
O5	0.0529 (12)	0.0384 (10)	0.0695 (13)	−0.0036 (8)	−0.0314 (10)	0.0011 (9)
O6	0.0646 (12)	0.0254 (8)	0.0443 (9)	0.0064 (8)	−0.0065 (9)	0.0091 (7)
N6	0.0245 (9)	0.0229 (8)	0.0225 (8)	0.0036 (7)	0.0061 (7)	0.0016 (7)
C53	0.0195 (10)	0.0188 (9)	0.0188 (9)	0.0023 (7)	0.0024 (8)	0.0010 (7)
C54	0.0220 (10)	0.0265 (10)	0.0189 (9)	0.0021 (8)	0.0075 (8)	0.0039 (7)
C55	0.0329 (11)	0.0239 (10)	0.0227 (10)	0.0035 (8)	0.0102 (9)	−0.0025 (8)
C56	0.0328 (12)	0.0190 (9)	0.0295 (10)	−0.0003 (8)	0.0109 (9)	0.0007 (8)
C57	0.0310 (11)	0.0234 (10)	0.0262 (10)	0.0024 (8)	0.0133 (9)	0.0055 (8)
C58	0.0252 (10)	0.0230 (10)	0.0178 (9)	0.0058 (8)	0.0068 (8)	0.0017 (7)
O3	0.0590 (11)	0.0288 (8)	0.0286 (8)	0.0119 (7)	0.0271 (8)	0.0078 (6)
O4	0.0506 (10)	0.0275 (8)	0.0295 (8)	0.0105 (7)	0.0258 (7)	0.0053 (6)
N5	0.0276 (10)	0.0260 (9)	0.0221 (9)	0.0060 (8)	0.0088 (8)	0.0022 (7)
C59	0.0191 (10)	0.0205 (9)	0.0196 (9)	0.0024 (7)	0.0032 (8)	0.0016 (7)
C60	0.0240 (10)	0.0239 (10)	0.0189 (9)	0.0014 (8)	0.0076 (8)	0.0012 (7)
C61	0.0314 (11)	0.0256 (10)	0.0224 (10)	0.0064 (8)	0.0114 (9)	−0.0011 (8)
C62	0.0345 (12)	0.0217 (10)	0.0275 (10)	0.0039 (8)	0.0110 (9)	0.0023 (8)
C63	0.0290 (11)	0.0255 (10)	0.0238 (10)	0.0033 (8)	0.0105 (9)	0.0065 (8)
C64	0.0194 (10)	0.0278 (10)	0.0175 (9)	0.0018 (8)	0.0056 (8)	0.0003 (7)
O8	0.0362 (13)	0.0214 (11)	0.051 (2)	0.0010 (8)	0.0158 (11)	0.0047 (9)
O7	0.0306 (13)	0.0431 (13)	0.058 (2)	0.0179 (9)	0.0085 (11)	0.0116 (11)
O12	0.052 (6)	0.021 (4)	0.053 (8)	0.003 (4)	−0.016 (5)	−0.003 (4)
O11	0.069 (9)	0.049 (6)	0.045 (8)	0.033 (5)	−0.024 (6)	0.005 (4)

Geometric parameters (Å, º)

N1—C52	1.348 (2)	C23—C24	1.420 (3)
N1—C40	1.350 (3)	C23—H23	0.9300
C40—C41	1.426 (3)	C24—C25	1.350 (3)
C40—C45	1.435 (3)	C24—H24	0.9300
C41—C42	1.356 (3)	C25—C26	1.429 (3)
C41—H41	0.9300	C25—H25	0.9300
C42—C43	1.421 (3)	C7—C13	1.386 (3)
C42—H42	0.9300	C7—C1	1.391 (3)
C43—C44	1.354 (3)	C7—H7	0.9300
C43—H43	0.9300	C1—C2	1.430 (3)
C44—C45	1.425 (3)	C1—C6	1.435 (3)
C44—H44	0.9300	C2—C3	1.363 (3)
C45—C46	1.387 (3)	C2—H2	0.9300
C46—C47	1.398 (3)	C3—C4	1.416 (3)
C46—H46	0.9300	C3—H3	0.9300
C47—C48	1.428 (3)	C4—C5	1.363 (3)
C47—C52	1.430 (3)	C4—H4	0.9300
C48—C49	1.362 (3)	C5—C6	1.422 (3)
C48—H48	0.9300	C5—H5	0.9300
C49—C50	1.417 (3)	C6—N4	1.349 (2)
C49—H49	0.9300	N4—C8	1.350 (3)
C50—C51	1.358 (3)	C8—C9	1.422 (3)
C50—H50	0.9300	C8—C13	1.435 (3)
C51—C52	1.425 (3)	C9—C10	1.362 (3)
C51—H51	0.9300	C9—H9	0.9300
N2—C38	1.347 (2)	C10—C11	1.420 (3)
N2—C39	1.352 (2)	C10—H10	0.9300
C27—C28	1.357 (3)	C11—C12	1.356 (3)
C27—C39	1.423 (3)	C11—H11	0.9300
C27—H27	0.9300	C12—C13	1.427 (3)
C28—C29	1.424 (3)	C12—H12	0.9300
C28—H28	0.9300	O1—C54	1.350 (2)
C29—C30	1.348 (3)	O1—H1	0.8200
C29—H29	0.9300	O2—C58	1.340 (2)
C30—C31	1.427 (3)	O2—H2A	0.8200
C30—H30	0.9300	O5—N6	1.212 (2)
C31—C32	1.390 (3)	O6—N6	1.205 (2)
C31—C39	1.431 (3)	N6—C53	1.465 (2)
C32—C33	1.394 (3)	C53—C54	1.388 (2)
C32—H32	0.9300	C53—C58	1.394 (2)
C33—C34	1.426 (3)	C54—C55	1.391 (3)
C33—C38	1.438 (2)	C55—C56	1.384 (3)
C34—C35	1.358 (3)	C55—H55	0.9300
C34—H34	0.9300	C56—C57	1.380 (3)
C35—C36	1.425 (3)	C56—H56	0.9300
C35—H35	0.9300	C57—C58	1.393 (3)
C36—C37	1.356 (3)	C57—H57	0.9300
C36—H36	0.9300	O3—C60	1.337 (2)
C37—C38	1.423 (3)	O3—H3A	0.8200
C37—H37	0.9300	O4—C64	1.341 (2)
C20—C26	1.387 (3)	O4—H4A	0.8200
C20—C14	1.393 (3)	N5—O11	1.118 (8)
C20—H20	0.9300	N5—O8	1.210 (2)
C14—C15	1.421 (3)	N5—O7	1.242 (3)
C14—C19	1.434 (3)	N5—O12	1.262 (8)
C15—C16	1.361 (3)	N5—C59	1.467 (2)
C15—H15	0.9300	C59—C60	1.394 (2)
C16—C17	1.416 (3)	C59—C64	1.398 (2)
C16—H16	0.9300	C60—C61	1.396 (3)
C17—C18	1.358 (3)	C61—C62	1.387 (3)
C17—H17	0.9300	C61—H61	0.9300
C18—C19	1.428 (3)	C62—C63	1.383 (3)
C18—H18	0.9300	C62—H62	0.9300
C19—N3	1.347 (2)	C63—C64	1.390 (3)
N3—C21	1.352 (3)	C63—H63	0.9300
C21—C22	1.422 (3)	O8—O12	1.074 (12)
C21—C26	1.436 (3)	O8—O11	1.698 (11)
C22—C23	1.357 (3)	O7—O11	1.090 (15)
C22—H22	0.9300
C52—N1—C40	119.35 (16)	C25—C24—C23	120.4 (2)
N1—C40—C41	119.31 (18)	C25—C24—H24	119.8
N1—C40—C45	122.12 (18)	C23—C24—H24	119.8
C41—C40—C45	118.57 (19)	C24—C25—C26	120.67 (19)
C42—C41—C40	120.6 (2)	C24—C25—H25	119.7
C42—C41—H41	119.7	C26—C25—H25	119.7
C40—C41—H41	119.7	C20—C26—C25	123.25 (18)
C41—C42—C43	120.9 (2)	C20—C26—C21	118.00 (18)
C41—C42—H42	119.6	C25—C26—C21	118.74 (18)
C43—C42—H42	119.6	C13—C7—C1	120.53 (17)
C44—C43—C42	120.4 (2)	C13—C7—H7	119.7
C44—C43—H43	119.8	C1—C7—H7	119.7
C42—C43—H43	119.8	C7—C1—C2	123.21 (18)
C43—C44—C45	120.8 (2)	C7—C1—C6	118.02 (18)
C43—C44—H44	119.6	C2—C1—C6	118.77 (18)
C45—C44—H44	119.6	C3—C2—C1	120.58 (19)
C46—C45—C44	123.18 (19)	C3—C2—H2	119.7
C46—C45—C40	118.07 (18)	C1—C2—H2	119.7
C44—C45—C40	118.75 (19)	C2—C3—C4	120.3 (2)
C45—C46—C47	120.26 (18)	C2—C3—H3	119.9
C45—C46—H46	119.9	C4—C3—H3	119.9
C47—C46—H46	119.9	C5—C4—C3	121.1 (2)
C46—C47—C48	122.68 (18)	C5—C4—H4	119.4
C46—C47—C52	118.21 (18)	C3—C4—H4	119.4
C48—C47—C52	119.10 (18)	C4—C5—C6	120.47 (18)
C49—C48—C47	119.96 (19)	C4—C5—H5	119.8
C49—C48—H48	120.0	C6—C5—H5	119.8
C47—C48—H48	120.0	N4—C6—C5	119.12 (17)
C48—C49—C50	120.9 (2)	N4—C6—C1	122.11 (18)
C48—C49—H49	119.6	C5—C6—C1	118.78 (18)
C50—C49—H49	119.6	C6—N4—C8	119.08 (16)
C51—C50—C49	120.9 (2)	N4—C8—C9	119.31 (17)
C51—C50—H50	119.6	N4—C8—C13	122.16 (18)
C49—C50—H50	119.6	C9—C8—C13	118.53 (18)
C50—C51—C52	120.32 (19)	C10—C9—C8	120.66 (19)
C50—C51—H51	119.8	C10—C9—H9	119.7
C52—C51—H51	119.8	C8—C9—H9	119.7
N1—C52—C51	119.18 (17)	C9—C10—C11	120.9 (2)
N1—C52—C47	121.96 (18)	C9—C10—H10	119.6
C51—C52—C47	118.86 (18)	C11—C10—H10	119.6
C38—N2—C39	119.52 (16)	C12—C11—C10	120.3 (2)
C28—C27—C39	120.4 (2)	C12—C11—H11	119.9
C28—C27—H27	119.8	C10—C11—H11	119.9
C39—C27—H27	119.8	C11—C12—C13	120.84 (19)
C27—C28—C29	120.9 (2)	C11—C12—H12	119.6
C27—C28—H28	119.5	C13—C12—H12	119.6
C29—C28—H28	119.5	C7—C13—C12	123.07 (18)
C30—C29—C28	120.1 (2)	C7—C13—C8	118.09 (18)
C30—C29—H29	119.9	C12—C13—C8	118.83 (19)
C28—C29—H29	119.9	C54—O1—H1	109.5
C29—C30—C31	121.2 (2)	C58—O2—H2A	109.5
C29—C30—H30	119.4	O6—N6—O5	122.75 (17)
C31—C30—H30	119.4	O6—N6—C53	119.65 (16)
C32—C31—C30	123.40 (18)	O5—N6—C53	117.60 (16)
C32—C31—C39	118.10 (18)	C54—C53—C58	122.76 (16)
C30—C31—C39	118.50 (18)	C54—C53—N6	118.42 (15)
C31—C32—C33	120.47 (17)	C58—C53—N6	118.75 (15)
C31—C32—H32	119.8	O1—C54—C53	117.34 (16)
C33—C32—H32	119.8	O1—C54—C55	124.06 (17)
C32—C33—C34	123.30 (17)	C53—C54—C55	118.57 (16)
C32—C33—C38	118.00 (17)	C56—C55—C54	118.99 (17)
C34—C33—C38	118.70 (18)	C56—C55—H55	120.5
C35—C34—C33	120.65 (18)	C54—C55—H55	120.5
C35—C34—H34	119.7	C57—C56—C55	122.22 (18)
C33—C34—H34	119.7	C57—C56—H56	118.9
C34—C35—C36	120.41 (19)	C55—C56—H56	118.9
C34—C35—H35	119.8	C56—C57—C58	119.72 (17)
C36—C35—H35	119.8	C56—C57—H57	120.1
C37—C36—C35	120.92 (19)	C58—C57—H57	120.1
C37—C36—H36	119.5	O2—C58—C57	124.49 (16)
C35—C36—H36	119.5	O2—C58—C53	117.79 (16)
C36—C37—C38	120.50 (18)	C57—C58—C53	117.71 (16)
C36—C37—H37	119.8	C60—O3—H3A	109.5
C38—C37—H37	119.8	C64—O4—H4A	109.5
N2—C38—C37	119.35 (16)	O11—N5—O8	93.5 (8)
N2—C38—C33	121.82 (17)	O11—N5—O7	54.7 (8)
C37—C38—C33	118.82 (17)	O8—N5—O7	122.64 (19)
N2—C39—C27	119.09 (17)	O11—N5—O12	125.3 (6)
N2—C39—C31	122.06 (17)	O8—N5—O12	51.5 (5)
C27—C39—C31	118.85 (18)	O7—N5—O12	105.6 (5)
C26—C20—C14	120.69 (17)	O11—N5—C59	120.2 (5)
C26—C20—H20	119.7	O8—N5—C59	120.36 (17)
C14—C20—H20	119.7	O7—N5—C59	116.97 (17)
C20—C14—C15	123.11 (18)	O12—N5—C59	114.1 (4)
C20—C14—C19	117.72 (18)	C60—C59—C64	122.66 (16)
C15—C14—C19	119.17 (19)	C60—C59—N5	118.86 (15)
C16—C15—C14	120.58 (19)	C64—C59—N5	118.44 (16)
C16—C15—H15	119.7	O3—C60—C59	118.15 (16)
C14—C15—H15	119.7	O3—C60—C61	123.83 (16)
C15—C16—C17	120.2 (2)	C59—C60—C61	118.01 (16)
C15—C16—H16	119.9	C62—C61—C60	119.63 (17)
C17—C16—H16	119.9	C62—C61—H61	120.2
C18—C17—C16	121.3 (2)	C60—C61—H61	120.2
C18—C17—H17	119.4	C63—C62—C61	121.70 (18)
C16—C17—H17	119.4	C63—C62—H62	119.2
C17—C18—C19	120.32 (19)	C61—C62—H62	119.2
C17—C18—H18	119.8	C62—C63—C64	119.94 (17)
C19—C18—H18	119.8	C62—C63—H63	120.0
N3—C19—C18	119.18 (17)	C64—C63—H63	120.0
N3—C19—C14	122.43 (18)	O4—C64—C63	123.84 (16)
C18—C19—C14	118.40 (18)	O4—C64—C59	118.09 (16)
C19—N3—C21	119.08 (16)	C63—C64—C59	118.03 (16)
N3—C21—C22	119.29 (17)	O12—O8—N5	66.7 (4)
N3—C21—C26	122.07 (17)	O12—O8—O11	96.9 (7)
C22—C21—C26	118.64 (18)	N5—O8—O11	41.1 (4)
C23—C22—C21	120.39 (19)	O11—O7—N5	56.8 (4)
C23—C22—H22	119.8	O8—O12—N5	61.8 (6)
C21—C22—H22	119.8	O7—O11—N5	68.5 (8)
C22—C23—C24	121.1 (2)	O7—O11—O8	98.7 (7)
C22—C23—H23	119.4	N5—O11—O8	45.4 (4)
C24—C23—H23	119.4
C52—N1—C40—C41	179.26 (16)	C7—C1—C2—C3	179.82 (19)
C52—N1—C40—C45	−1.5 (3)	C6—C1—C2—C3	0.1 (3)
N1—C40—C41—C42	179.34 (18)	C1—C2—C3—C4	0.9 (3)
C45—C40—C41—C42	0.1 (3)	C2—C3—C4—C5	−1.0 (3)
C40—C41—C42—C43	0.1 (3)	C3—C4—C5—C6	0.1 (3)
C41—C42—C43—C44	−0.4 (3)	C4—C5—C6—N4	−179.56 (17)
C42—C43—C44—C45	0.6 (3)	C4—C5—C6—C1	0.9 (3)
C43—C44—C45—C46	179.82 (19)	C7—C1—C6—N4	−0.3 (3)
C43—C44—C45—C40	−0.4 (3)	C2—C1—C6—N4	179.46 (17)
N1—C40—C45—C46	0.6 (3)	C7—C1—C6—C5	179.31 (17)
C41—C40—C45—C46	179.86 (17)	C2—C1—C6—C5	−1.0 (3)
N1—C40—C45—C44	−179.19 (17)	C5—C6—N4—C8	−178.82 (16)
C41—C40—C45—C44	0.0 (3)	C1—C6—N4—C8	0.7 (3)
C44—C45—C46—C47	−179.50 (17)	C6—N4—C8—C9	179.25 (16)
C40—C45—C46—C47	0.7 (3)	C6—N4—C8—C13	−0.5 (3)
C45—C46—C47—C48	179.36 (17)	N4—C8—C9—C10	−179.87 (17)
C45—C46—C47—C52	−1.1 (3)	C13—C8—C9—C10	−0.1 (3)
C46—C47—C48—C49	179.60 (18)	C8—C9—C10—C11	−0.1 (3)
C52—C47—C48—C49	0.1 (3)	C9—C10—C11—C12	−0.5 (3)
C47—C48—C49—C50	−0.5 (3)	C10—C11—C12—C13	1.2 (3)
C48—C49—C50—C51	0.5 (3)	C1—C7—C13—C12	179.90 (17)
C49—C50—C51—C52	0.0 (3)	C1—C7—C13—C8	0.7 (3)
C40—N1—C52—C51	−179.49 (16)	C11—C12—C13—C7	179.40 (18)
C40—N1—C52—C47	1.1 (3)	C11—C12—C13—C8	−1.4 (3)
C50—C51—C52—N1	−179.79 (17)	N4—C8—C13—C7	−0.2 (3)
C50—C51—C52—C47	−0.4 (3)	C9—C8—C13—C7	−179.95 (17)
C46—C47—C52—N1	0.2 (3)	N4—C8—C13—C12	−179.44 (16)
C48—C47—C52—N1	179.77 (16)	C9—C8—C13—C12	0.8 (3)
C46—C47—C52—C51	−179.22 (16)	O6—N6—C53—C54	69.9 (2)
C48—C47—C52—C51	0.3 (3)	O5—N6—C53—C54	−109.5 (2)
C39—C27—C28—C29	−0.2 (3)	O6—N6—C53—C58	−113.0 (2)
C27—C28—C29—C30	0.7 (3)	O5—N6—C53—C58	67.6 (2)
C28—C29—C30—C31	−0.8 (3)	C58—C53—C54—O1	179.89 (17)
C29—C30—C31—C32	179.75 (19)	N6—C53—C54—O1	−3.1 (3)
C29—C30—C31—C39	0.4 (3)	C58—C53—C54—C55	−2.0 (3)
C30—C31—C32—C33	179.15 (17)	N6—C53—C54—C55	175.02 (17)
C39—C31—C32—C33	−1.5 (3)	O1—C54—C55—C56	178.88 (19)
C31—C32—C33—C34	−178.97 (17)	C53—C54—C55—C56	0.9 (3)
C31—C32—C33—C38	1.2 (3)	C54—C55—C56—C57	0.9 (3)
C32—C33—C34—C35	179.69 (18)	C55—C56—C57—C58	−1.6 (3)
C38—C33—C34—C35	−0.4 (3)	C56—C57—C58—O2	179.09 (19)
C33—C34—C35—C36	0.5 (3)	C56—C57—C58—C53	0.5 (3)
C34—C35—C36—C37	0.0 (3)	C54—C53—C58—O2	−177.42 (17)
C35—C36—C37—C38	−0.6 (3)	N6—C53—C58—O2	5.6 (3)
C39—N2—C38—C37	178.99 (16)	C54—C53—C58—C57	1.3 (3)
C39—N2—C38—C33	−1.8 (3)	N6—C53—C58—C57	−175.71 (17)
C36—C37—C38—N2	179.91 (17)	O11—N5—C59—C60	−57.5 (11)
C36—C37—C38—C33	0.6 (3)	O8—N5—C59—C60	57.6 (3)
C32—C33—C38—N2	0.5 (3)	O7—N5—C59—C60	−120.4 (2)
C34—C33—C38—N2	−179.37 (16)	O12—N5—C59—C60	115.7 (7)
C32—C33—C38—C37	179.75 (16)	O11—N5—C59—C64	120.4 (10)
C34—C33—C38—C37	−0.1 (3)	O8—N5—C59—C64	−124.5 (2)
C38—N2—C39—C27	−179.11 (16)	O7—N5—C59—C64	57.5 (3)
C38—N2—C39—C31	1.4 (3)	O12—N5—C59—C64	−66.4 (7)
C28—C27—C39—N2	−179.74 (18)	C64—C59—C60—O3	179.56 (18)
C28—C27—C39—C31	−0.2 (3)	N5—C59—C60—O3	−2.6 (3)
C32—C31—C39—N2	0.2 (3)	C64—C59—C60—C61	−1.9 (3)
C30—C31—C39—N2	179.61 (17)	N5—C59—C60—C61	175.88 (17)
C32—C31—C39—C27	−179.26 (17)	O3—C60—C61—C62	179.04 (19)
C30—C31—C39—C27	0.1 (3)	C59—C60—C61—C62	0.6 (3)
C26—C20—C14—C15	179.46 (17)	C60—C61—C62—C63	0.9 (3)
C26—C20—C14—C19	−0.6 (3)	C61—C62—C63—C64	−1.2 (3)
C20—C14—C15—C16	179.43 (19)	C62—C63—C64—O4	177.61 (19)
C19—C14—C15—C16	−0.5 (3)	C62—C63—C64—C59	0.0 (3)
C14—C15—C16—C17	−0.6 (3)	C60—C59—C64—O4	−176.14 (17)
C15—C16—C17—C18	1.2 (3)	N5—C59—C64—O4	6.0 (3)
C16—C17—C18—C19	−0.6 (3)	C60—C59—C64—C63	1.7 (3)
C17—C18—C19—N3	179.11 (17)	N5—C59—C64—C63	−176.18 (17)
C17—C18—C19—C14	−0.5 (3)	O11—N5—O8—O12	−133.7 (8)
C20—C14—C19—N3	1.5 (3)	O7—N5—O8—O12	−84.1 (6)
C15—C14—C19—N3	−178.52 (17)	C59—N5—O8—O12	98.0 (5)
C20—C14—C19—C18	−178.86 (17)	O7—N5—O8—O11	49.6 (6)
C15—C14—C19—C18	1.1 (3)	O12—N5—O8—O11	133.7 (8)
C18—C19—N3—C21	179.04 (16)	C59—N5—O8—O11	−128.3 (7)
C14—C19—N3—C21	−1.4 (3)	O8—N5—O7—O11	−68.7 (7)
C19—N3—C21—C22	−179.72 (16)	O12—N5—O7—O11	−122.6 (8)
C19—N3—C21—C26	0.3 (3)	C59—N5—O7—O11	109.3 (6)
N3—C21—C22—C23	179.15 (17)	O11—O8—O12—N5	−28.6 (4)
C26—C21—C22—C23	−0.8 (3)	O11—N5—O12—O8	62.1 (13)
C21—C22—C23—C24	0.6 (3)	O7—N5—O12—O8	119.6 (4)
C22—C23—C24—C25	0.7 (3)	C59—N5—O12—O8	−110.6 (4)
C23—C24—C25—C26	−1.8 (3)	N5—O7—O11—O8	34.4 (2)
C14—C20—C26—C25	−179.57 (17)	O8—N5—O11—O7	128.2 (4)
C14—C20—C26—C21	−0.4 (3)	O12—N5—O11—O7	84.3 (11)
C24—C25—C26—C20	−179.34 (18)	C59—N5—O11—O7	−103.3 (5)
C24—C25—C26—C21	1.5 (3)	O7—N5—O11—O8	−128.2 (4)
N3—C21—C26—C20	0.6 (3)	O12—N5—O11—O8	−43.9 (9)
C22—C21—C26—C20	−179.39 (16)	C59—N5—O11—O8	128.5 (6)
N3—C21—C26—C25	179.82 (16)	O12—O8—O11—O7	−5.7 (7)
C22—C21—C26—C25	−0.2 (3)	N5—O8—O11—O7	−47.7 (6)
C13—C7—C1—C2	179.84 (17)	O12—O8—O11—N5	42.0 (7)
C13—C7—C1—C6	−0.5 (3)

(4NRES-DMP)

Crystal data

C12H13N3O4	F(000) = 552
Mr = 263.25	Dx = 1.392 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.7482 (14) Å	Cell parameters from 4346 reflections
b = 14.926 (3) Å	θ = 3.5–27.6°
c = 10.2464 (17) Å	µ = 0.11 mm^−1
β = 110.165 (8)°	T = 150 K
V = 1255.9 (4) Å^3	Block, brown
Z = 4	0.26 × 0.21 × 0.17 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	859 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.065
profile data from ω–scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −11→11
Tmin = 0.793, Tmax = 1.000	k = −19→19
6402 measured reflections	l = −13→13
1441 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.057	w = 1/[σ^2(Fo^2) + (0.1096P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.199	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.34 e Å^−3
1441 reflections	Δρmin = −0.22 e Å^−3
90 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.019 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.000000	0.44224 (18)	0.250000	0.0487 (8)
O1	0.28383 (18)	0.35093 (11)	0.34731 (19)	0.0559 (6)
H1	0.364390	0.318473	0.371599	0.084*
C6	0.7062 (3)	0.33684 (14)	0.4823 (2)	0.0418 (6)
C3	0.1487 (3)	0.30020 (15)	0.3006 (2)	0.0415 (6)
N2	0.5878 (2)	0.27505 (13)	0.43909 (18)	0.0440 (6)
C1	0.000000	0.1629 (2)	0.250000	0.0554 (9)
H1A	0.000000	0.100585	0.250000	0.066*
C7	0.8662 (3)	0.31027 (14)	0.5418 (2)	0.0452 (6)
H7	0.946105	0.354302	0.570073	0.054*
C4	0.000000	0.34430 (19)	0.250000	0.0385 (7)
C2	0.1472 (3)	0.20758 (16)	0.3021 (2)	0.0509 (7)
H2	0.244026	0.175666	0.337774	0.061*
O2	0.0475 (3)	0.48063 (13)	0.1684 (2)	0.0884 (8)
C8	0.6575 (3)	0.43299 (15)	0.4621 (3)	0.0655 (8)
H8A	0.752696	0.470049	0.497064	0.098*
H8B	0.603902	0.444697	0.364819	0.098*
H8C	0.584685	0.446146	0.511369	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0235 (14)	0.0466 (17)	0.0668 (19)	0.000	0.0038 (14)	0.000
O1	0.0243 (9)	0.0519 (11)	0.0802 (13)	0.0051 (7)	0.0035 (9)	0.0034 (8)
C6	0.0324 (12)	0.0406 (13)	0.0506 (13)	0.0046 (10)	0.0121 (11)	−0.0037 (9)
C3	0.0329 (13)	0.0469 (14)	0.0403 (12)	−0.0001 (10)	0.0070 (10)	−0.0002 (9)
N2	0.0325 (11)	0.0429 (11)	0.0521 (12)	0.0056 (8)	0.0090 (9)	−0.0028 (8)
C1	0.056 (2)	0.0394 (18)	0.066 (2)	0.000	0.016 (2)	0.000
C7	0.0306 (12)	0.0410 (13)	0.0591 (14)	−0.0003 (10)	0.0093 (11)	−0.0063 (10)
C4	0.0311 (16)	0.0391 (17)	0.0424 (17)	0.000	0.0089 (14)	0.000
C2	0.0425 (15)	0.0503 (15)	0.0564 (15)	0.0107 (11)	0.0125 (13)	0.0051 (11)
O2	0.0965 (17)	0.0601 (13)	0.1218 (18)	0.0156 (12)	0.0547 (15)	0.0375 (11)
C8	0.0460 (17)	0.0444 (15)	0.101 (2)	0.0097 (12)	0.0185 (16)	−0.0035 (13)

Geometric parameters (Å, º)

N1—O2^i	1.200 (2)	C6—C8	1.491 (3)
N1—O2	1.200 (2)	C3—C2	1.383 (3)
N1—C4	1.462 (4)	C3—C4	1.389 (3)
O1—C3	1.345 (3)	N2—C7^ii	1.330 (3)
C6—N2	1.343 (3)	C1—C2	1.383 (3)
C6—C7	1.378 (3)	C1—C2^i	1.383 (3)
O2^i—N1—O2	123.0 (3)	C2—C3—C4	117.8 (2)
O2^i—N1—C4	118.52 (16)	C7^ii—N2—C6	116.69 (19)
O2—N1—C4	118.52 (16)	C2—C1—C2^i	122.3 (3)
N2—C6—C7	119.9 (2)	N2^ii—C7—C6	123.4 (2)
N2—C6—C8	117.7 (2)	C3—C4—C3^i	123.4 (3)
C7—C6—C8	122.4 (2)	C3—C4—N1	118.29 (14)
O1—C3—C2	124.7 (2)	C3^i—C4—N1	118.29 (14)
O1—C3—C4	117.5 (2)	C3—C2—C1	119.3 (2)

Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+3/2, −y+1/2, −z+1.

(5NRES-9AACR)

Crystal data

C19H15N3O4	Z = 2
Mr = 349.34	F(000) = 364
Triclinic, P1	Dx = 1.475 Mg m^−3
a = 7.7638 (14) Å	Mo Kα radiation, λ = 0.71075 Å
b = 8.5897 (15) Å	Cell parameters from 5658 reflections
c = 12.723 (2) Å	θ = 3.4–27.6°
α = 105.585 (7)°	µ = 0.11 mm^−1
β = 102.978 (7)°	T = 150 K
γ = 95.062 (7)°	Block, yellow
V = 786.3 (2) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2234 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.039
profile data from ω–scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −10→10
Tmin = 0.744, Tmax = 1.000	k = −11→11
7168 measured reflections	l = −16→16
3538 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.177	w = 1/[σ^2(Fo^2) + (0.0982P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3538 reflections	Δρmax = 0.31 e Å^−3
236 parameters	Δρmin = −0.36 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5554 (2)	0.10015 (18)	0.27152 (12)	0.0271 (4)
O2	0.7822 (2)	−0.22913 (19)	−0.02638 (13)	0.0326 (4)
H2	0.872474	−0.160678	0.005270	0.049*
O3	0.9559 (2)	0.0378 (2)	0.10529 (14)	0.0427 (5)
N1	0.2317 (2)	0.6350 (2)	0.55075 (14)	0.0228 (4)
H1	0.236536	0.715373	0.609291	0.027*
N3	0.8378 (2)	0.0623 (2)	0.15944 (15)	0.0265 (4)
O4	0.8673 (2)	0.1826 (2)	0.24322 (15)	0.0479 (6)
N2	0.2836 (2)	0.2822 (2)	0.27473 (14)	0.0261 (5)
H2A	0.334962	0.200456	0.284268	0.031*
H2B	0.254118	0.295055	0.208644	0.031*
C13	0.2875 (3)	0.4950 (2)	0.56593 (17)	0.0209 (5)
C19	0.2503 (3)	0.3873 (3)	0.36111 (17)	0.0209 (5)
C18	0.2996 (3)	0.3662 (2)	0.47215 (17)	0.0198 (5)
C12	0.1689 (3)	0.6527 (3)	0.44704 (17)	0.0218 (5)
C1	0.6759 (3)	−0.0486 (2)	0.12276 (16)	0.0208 (5)
C7	0.1683 (3)	0.5280 (3)	0.34856 (17)	0.0210 (5)
C2	0.5357 (3)	−0.0162 (2)	0.17994 (17)	0.0215 (5)
C6	0.6514 (3)	−0.1911 (3)	0.02691 (17)	0.0235 (5)
C17	0.3608 (3)	0.2233 (3)	0.49234 (18)	0.0247 (5)
H17	0.369752	0.137689	0.431992	0.030*
C9	0.0338 (3)	0.6917 (3)	0.2342 (2)	0.0302 (5)
H9	−0.014418	0.704275	0.163654	0.036*
C14	0.3363 (3)	0.4786 (3)	0.67554 (18)	0.0255 (5)
H14	0.328380	0.562768	0.737099	0.031*
C15	0.3951 (3)	0.3398 (3)	0.69155 (19)	0.0291 (5)
H15	0.427984	0.330593	0.764300	0.035*
C5	0.4916 (3)	−0.2950 (3)	−0.01254 (18)	0.0317 (6)
H5	0.476196	−0.389643	−0.072457	0.038*
C4	0.3512 (3)	−0.2580 (3)	0.03798 (19)	0.0330 (6)
H4	0.241568	−0.326953	0.008483	0.040*
C11	0.1083 (3)	0.7995 (3)	0.43761 (19)	0.0287 (5)
H11	0.113244	0.883952	0.502319	0.034*
C8	0.0968 (3)	0.5510 (3)	0.24207 (18)	0.0267 (5)
H8	0.092856	0.468709	0.176472	0.032*
C16	0.4067 (3)	0.2101 (3)	0.59960 (19)	0.0275 (5)
H16	0.445591	0.115463	0.611738	0.033*
C3	0.3702 (3)	−0.1246 (3)	0.12860 (19)	0.0297 (5)
H3	0.272379	−0.103574	0.157948	0.036*
C10	0.0420 (3)	0.8178 (3)	0.3331 (2)	0.0319 (6)
H10	0.001879	0.914882	0.327386	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0261 (8)	0.0255 (8)	0.0258 (8)	0.0022 (7)	0.0108 (7)	−0.0017 (7)
O2	0.0392 (10)	0.0329 (10)	0.0232 (8)	0.0083 (8)	0.0119 (8)	0.0003 (7)
O3	0.0274 (10)	0.0594 (12)	0.0320 (10)	−0.0035 (8)	0.0169 (8)	−0.0060 (9)
N1	0.0263 (10)	0.0196 (9)	0.0197 (9)	0.0057 (8)	0.0069 (8)	−0.0002 (7)
N3	0.0245 (10)	0.0286 (10)	0.0235 (10)	0.0032 (8)	0.0089 (8)	0.0013 (8)
O4	0.0324 (10)	0.0390 (11)	0.0518 (11)	−0.0100 (8)	0.0209 (9)	−0.0236 (9)
N2	0.0288 (10)	0.0261 (10)	0.0205 (9)	0.0074 (8)	0.0050 (8)	0.0022 (8)
C13	0.0176 (11)	0.0188 (11)	0.0233 (11)	−0.0002 (9)	0.0069 (9)	0.0008 (9)
C19	0.0159 (10)	0.0217 (11)	0.0205 (11)	−0.0026 (8)	0.0057 (9)	−0.0006 (8)
C18	0.0176 (10)	0.0177 (10)	0.0223 (11)	0.0007 (8)	0.0062 (9)	0.0030 (8)
C12	0.0188 (11)	0.0209 (11)	0.0243 (11)	0.0006 (9)	0.0075 (9)	0.0037 (9)
C1	0.0243 (11)	0.0161 (10)	0.0204 (11)	0.0037 (9)	0.0043 (9)	0.0041 (9)
C7	0.0175 (10)	0.0213 (11)	0.0231 (11)	0.0003 (8)	0.0065 (9)	0.0046 (9)
C2	0.0239 (11)	0.0190 (11)	0.0235 (11)	0.0054 (9)	0.0078 (9)	0.0076 (9)
C6	0.0308 (12)	0.0243 (11)	0.0166 (10)	0.0096 (10)	0.0064 (9)	0.0061 (9)
C17	0.0231 (12)	0.0225 (11)	0.0276 (12)	0.0040 (9)	0.0104 (10)	0.0026 (9)
C9	0.0300 (13)	0.0359 (13)	0.0274 (12)	0.0050 (11)	0.0066 (10)	0.0145 (10)
C14	0.0273 (12)	0.0248 (12)	0.0208 (11)	0.0024 (9)	0.0066 (10)	0.0009 (9)
C15	0.0297 (12)	0.0320 (13)	0.0243 (12)	0.0011 (10)	0.0077 (10)	0.0068 (10)
C5	0.0468 (15)	0.0218 (12)	0.0188 (11)	0.0011 (11)	0.0018 (11)	0.0003 (9)
C4	0.0305 (13)	0.0296 (13)	0.0297 (13)	−0.0081 (11)	−0.0027 (11)	0.0068 (10)
C11	0.0309 (13)	0.0234 (12)	0.0313 (12)	0.0054 (10)	0.0106 (10)	0.0049 (10)
C8	0.0251 (12)	0.0296 (12)	0.0222 (11)	0.0023 (10)	0.0054 (10)	0.0035 (9)
C16	0.0275 (12)	0.0236 (12)	0.0334 (13)	0.0069 (10)	0.0099 (11)	0.0094 (10)
C3	0.0240 (12)	0.0313 (13)	0.0330 (13)	0.0016 (10)	0.0091 (10)	0.0078 (10)
C10	0.0337 (13)	0.0288 (13)	0.0363 (14)	0.0081 (10)	0.0107 (11)	0.0125 (11)

Geometric parameters (Å, º)

O1—C2	1.283 (2)	C2—C3	1.425 (3)
O2—C6	1.359 (3)	C6—C5	1.368 (3)
O2—H2	0.8200	C17—C16	1.369 (3)
O3—N3	1.264 (2)	C17—H17	0.9300
N1—C12	1.354 (3)	C9—C8	1.363 (3)
N1—C13	1.360 (3)	C9—C10	1.408 (3)
N1—H1	0.8600	C9—H9	0.9300
N3—O4	1.230 (2)	C14—C15	1.362 (3)
N3—C1	1.411 (3)	C14—H14	0.9300
N2—C19	1.314 (2)	C15—C16	1.408 (3)
N2—H2A	0.8600	C15—H15	0.9300
N2—H2B	0.8600	C5—C4	1.403 (3)
C13—C14	1.409 (3)	C5—H5	0.9300
C13—C18	1.420 (3)	C4—C3	1.359 (3)
C19—C18	1.443 (3)	C4—H4	0.9300
C19—C7	1.444 (3)	C11—C10	1.370 (3)
C18—C17	1.420 (3)	C11—H11	0.9300
C12—C7	1.411 (3)	C8—H8	0.9300
C12—C11	1.410 (3)	C16—H16	0.9300
C1—C6	1.440 (3)	C3—H3	0.9300
C1—C2	1.446 (3)	C10—H10	0.9300
C7—C8	1.417 (3)
C6—O2—H2	109.5	C16—C17—C18	120.8 (2)
C12—N1—C13	122.56 (17)	C16—C17—H17	119.6
C12—N1—H1	118.7	C18—C17—H17	119.6
C13—N1—H1	118.7	C8—C9—C10	119.8 (2)
O4—N3—O3	118.99 (18)	C8—C9—H9	120.1
O4—N3—C1	121.52 (18)	C10—C9—H9	120.1
O3—N3—C1	119.48 (17)	C15—C14—C13	120.2 (2)
C19—N2—H2A	120.0	C15—C14—H14	119.9
C19—N2—H2B	120.0	C13—C14—H14	119.9
H2A—N2—H2B	120.0	C14—C15—C16	121.0 (2)
N1—C13—C14	119.86 (18)	C14—C15—H15	119.5
N1—C13—C18	120.37 (19)	C16—C15—H15	119.5
C14—C13—C18	119.8 (2)	C6—C5—C4	119.6 (2)
N2—C19—C18	120.2 (2)	C6—C5—H5	120.2
N2—C19—C7	121.42 (19)	C4—C5—H5	120.2
C18—C19—C7	118.35 (18)	C3—C4—C5	122.2 (2)
C13—C18—C17	118.3 (2)	C3—C4—H4	118.9
C13—C18—C19	118.46 (19)	C5—C4—H4	118.9
C17—C18—C19	123.19 (19)	C10—C11—C12	120.0 (2)
N1—C12—C7	120.83 (19)	C10—C11—H11	120.0
N1—C12—C11	119.48 (18)	C12—C11—H11	120.0
C7—C12—C11	119.7 (2)	C9—C8—C7	121.1 (2)
N3—C1—C6	119.22 (18)	C9—C8—H8	119.4
N3—C1—C2	119.85 (17)	C7—C8—H8	119.4
C6—C1—C2	120.92 (18)	C17—C16—C15	119.9 (2)
C12—C7—C8	118.5 (2)	C17—C16—H16	120.0
C12—C7—C19	118.39 (19)	C15—C16—H16	120.0
C8—C7—C19	122.96 (19)	C4—C3—C2	121.9 (2)
O1—C2—C3	120.8 (2)	C4—C3—H3	119.0
O1—C2—C1	123.67 (19)	C2—C3—H3	119.0
C3—C2—C1	115.49 (19)	C11—C10—C9	120.9 (2)
O2—C6—C5	117.70 (19)	C11—C10—H10	119.6
O2—C6—C1	122.68 (19)	C9—C10—H10	119.6
C5—C6—C1	119.6 (2)

(6NRES-33BP)

Crystal data

C26H21N5O4	Z = 2
Mr = 467.48	F(000) = 488
Triclinic, P1	Dx = 1.391 Mg m^−3
a = 7.3217 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6513 (13) Å	Cell parameters from 10398 reflections
c = 13.9987 (16) Å	θ = 3.1–27.6°
α = 105.915 (7)°	µ = 0.10 mm^−1
β = 102.665 (7)°	T = 150 K
γ = 91.242 (6)°	Block, yellow
V = 1116.2 (2) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	4075 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.023
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.888, Tmax = 1.000	k = −15→15
11717 measured reflections	l = −18→18
5120 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 0.2648P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
5120 reflections	Δρmax = 0.25 e Å^−3
318 parameters	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O2	0.62535 (13)	−0.01397 (8)	0.37342 (7)	0.0223 (2)
H2	0.641170	0.054860	0.370726	0.033*
O1	0.93638 (13)	−0.34882 (8)	0.41651 (7)	0.0224 (2)
H1	1.020157	−0.388530	0.398165	0.034*
O4	0.51596 (14)	−0.30008 (10)	0.32253 (8)	0.0337 (3)
O3	0.58962 (15)	−0.22002 (11)	0.48531 (8)	0.0372 (3)
N2	0.65425 (16)	0.19231 (10)	0.32435 (9)	0.0227 (3)
N1	0.62009 (15)	−0.23644 (10)	0.40083 (8)	0.0187 (2)
N3	0.77484 (17)	0.01404 (11)	−0.07001 (9)	0.0284 (3)
N4	0.15102 (16)	0.48877 (10)	0.33818 (8)	0.0217 (2)
C7	0.65747 (19)	0.31084 (12)	0.36573 (10)	0.0224 (3)
H7	0.652692	0.339692	0.433927	0.027*
N5	0.26793 (17)	0.47096 (11)	−0.05175 (9)	0.0262 (3)
C2	0.95337 (18)	−0.24026 (11)	0.40054 (9)	0.0169 (3)
C5	0.95771 (19)	−0.01179 (12)	0.37179 (9)	0.0198 (3)
H5	0.961842	0.063836	0.361827	0.024*
C8	0.66768 (19)	0.39178 (12)	0.31041 (10)	0.0225 (3)
H8	0.668643	0.473514	0.340960	0.027*
C25	0.2032 (2)	0.37109 (13)	−0.12776 (10)	0.0255 (3)
H25	0.209181	0.370682	−0.193531	0.031*
C6	0.78975 (18)	−0.06454 (12)	0.37842 (9)	0.0175 (3)
C3	1.11915 (18)	−0.18578 (12)	0.39408 (10)	0.0208 (3)
H3	1.228918	−0.224685	0.399055	0.025*
C17	0.16363 (19)	0.38823 (13)	0.36748 (10)	0.0230 (3)
H17	0.158415	0.392356	0.434112	0.028*
C22	0.18462 (18)	0.37099 (12)	0.06467 (9)	0.0184 (3)
C23	0.11819 (19)	0.26859 (13)	−0.01687 (10)	0.0235 (3)
H23	0.067616	0.200779	−0.005805	0.028*
C18	0.18402 (19)	0.27911 (12)	0.30256 (10)	0.0226 (3)
H18	0.193401	0.211312	0.325595	0.027*
C20	0.17866 (17)	0.37416 (12)	0.17056 (9)	0.0170 (3)
C12	0.68266 (18)	0.17468 (12)	0.05662 (10)	0.0189 (3)
C14	0.60805 (19)	0.22874 (13)	−0.01910 (10)	0.0228 (3)
H14	0.553323	0.300652	−0.002637	0.027*
C1	0.79311 (17)	−0.17821 (11)	0.39235 (9)	0.0156 (3)
C21	0.15935 (18)	0.48038 (12)	0.24181 (10)	0.0197 (3)
H21	0.151736	0.549902	0.221242	0.024*
C10	0.67462 (17)	0.22681 (12)	0.16446 (10)	0.0184 (3)
C19	0.19042 (18)	0.27104 (12)	0.20308 (10)	0.0200 (3)
H19	0.202443	0.197684	0.158289	0.024*
C16	0.6994 (2)	0.06804 (13)	−0.14041 (11)	0.0280 (3)
H16	0.703288	0.031777	−0.207885	0.034*
C11	0.66194 (18)	0.15294 (12)	0.22636 (10)	0.0207 (3)
H11	0.658610	0.070671	0.197519	0.025*
C26	0.25837 (19)	0.46885 (12)	0.04215 (10)	0.0229 (3)
H26	0.304092	0.537377	0.095948	0.027*
C4	1.11832 (18)	−0.07265 (13)	0.38011 (9)	0.0214 (3)
H4	1.229586	−0.036173	0.376162	0.026*
C15	0.6164 (2)	0.17415 (14)	−0.11897 (11)	0.0277 (3)
H15	0.566857	0.208459	−0.170666	0.033*
C9	0.67644 (18)	0.34953 (12)	0.20903 (10)	0.0207 (3)
H9	0.683489	0.402817	0.170933	0.025*
C24	0.1283 (2)	0.26893 (13)	−0.11444 (10)	0.0263 (3)
H24	0.085367	0.201493	−0.169766	0.032*
C13	0.7658 (2)	0.06833 (12)	0.02637 (11)	0.0241 (3)
H13	0.818620	0.032535	0.076518	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0210 (5)	0.0210 (5)	0.0294 (5)	0.0051 (4)	0.0066 (4)	0.0135 (4)
O1	0.0235 (5)	0.0202 (5)	0.0288 (5)	0.0089 (4)	0.0127 (4)	0.0100 (4)
O4	0.0251 (5)	0.0351 (6)	0.0335 (6)	−0.0103 (5)	0.0057 (5)	−0.0001 (5)
O3	0.0282 (6)	0.0646 (8)	0.0261 (5)	−0.0016 (5)	0.0114 (4)	0.0213 (5)
N2	0.0242 (6)	0.0224 (6)	0.0251 (6)	0.0034 (5)	0.0069 (5)	0.0115 (5)
N1	0.0168 (5)	0.0199 (6)	0.0232 (6)	0.0045 (4)	0.0062 (4)	0.0110 (5)
N3	0.0301 (7)	0.0244 (7)	0.0273 (6)	0.0022 (5)	0.0078 (5)	0.0011 (5)
N4	0.0238 (6)	0.0228 (6)	0.0205 (6)	0.0059 (5)	0.0084 (5)	0.0066 (5)
C7	0.0213 (7)	0.0251 (7)	0.0207 (6)	0.0013 (6)	0.0047 (5)	0.0065 (6)
N5	0.0334 (7)	0.0274 (7)	0.0207 (6)	0.0017 (5)	0.0077 (5)	0.0104 (5)
C2	0.0197 (6)	0.0176 (6)	0.0123 (6)	0.0018 (5)	0.0039 (5)	0.0023 (5)
C5	0.0245 (7)	0.0184 (7)	0.0164 (6)	−0.0028 (5)	0.0049 (5)	0.0054 (5)
C8	0.0238 (7)	0.0172 (7)	0.0252 (7)	−0.0003 (5)	0.0050 (5)	0.0046 (5)
C25	0.0283 (7)	0.0328 (8)	0.0171 (6)	0.0049 (6)	0.0062 (6)	0.0092 (6)
C6	0.0183 (6)	0.0203 (7)	0.0140 (6)	0.0022 (5)	0.0035 (5)	0.0055 (5)
C3	0.0167 (6)	0.0275 (7)	0.0180 (6)	0.0042 (5)	0.0058 (5)	0.0050 (5)
C17	0.0232 (7)	0.0303 (8)	0.0202 (6)	0.0064 (6)	0.0084 (5)	0.0118 (6)
C22	0.0165 (6)	0.0207 (7)	0.0186 (6)	0.0039 (5)	0.0049 (5)	0.0060 (5)
C23	0.0239 (7)	0.0228 (7)	0.0235 (7)	−0.0022 (6)	0.0058 (5)	0.0061 (6)
C18	0.0234 (7)	0.0221 (7)	0.0271 (7)	0.0044 (5)	0.0074 (6)	0.0134 (6)
C20	0.0139 (6)	0.0192 (7)	0.0189 (6)	0.0013 (5)	0.0048 (5)	0.0062 (5)
C12	0.0158 (6)	0.0188 (7)	0.0226 (6)	−0.0006 (5)	0.0041 (5)	0.0072 (5)
C14	0.0227 (7)	0.0220 (7)	0.0244 (7)	0.0027 (5)	0.0048 (5)	0.0084 (6)
C1	0.0151 (6)	0.0183 (6)	0.0129 (6)	−0.0013 (5)	0.0033 (5)	0.0039 (5)
C21	0.0203 (6)	0.0189 (7)	0.0218 (6)	0.0044 (5)	0.0068 (5)	0.0075 (5)
C10	0.0137 (6)	0.0197 (7)	0.0229 (7)	0.0015 (5)	0.0038 (5)	0.0084 (5)
C19	0.0192 (6)	0.0166 (7)	0.0233 (7)	0.0020 (5)	0.0053 (5)	0.0040 (5)
C16	0.0292 (8)	0.0298 (8)	0.0207 (7)	−0.0043 (6)	0.0063 (6)	0.0004 (6)
C11	0.0214 (7)	0.0168 (7)	0.0255 (7)	0.0028 (5)	0.0059 (5)	0.0081 (5)
C26	0.0283 (7)	0.0203 (7)	0.0192 (6)	−0.0001 (6)	0.0050 (5)	0.0048 (5)
C4	0.0188 (6)	0.0287 (7)	0.0156 (6)	−0.0046 (5)	0.0051 (5)	0.0041 (5)
C15	0.0279 (7)	0.0325 (8)	0.0227 (7)	−0.0003 (6)	0.0027 (6)	0.0104 (6)
C9	0.0190 (6)	0.0200 (7)	0.0256 (7)	0.0010 (5)	0.0047 (5)	0.0111 (5)
C24	0.0272 (7)	0.0281 (8)	0.0179 (6)	−0.0026 (6)	0.0023 (6)	0.0000 (6)
C13	0.0252 (7)	0.0216 (7)	0.0249 (7)	0.0021 (6)	0.0048 (6)	0.0061 (6)

Geometric parameters (Å, º)

O2—C6	1.3481 (15)	C25—C24	1.375 (2)
O1—C2	1.3512 (15)	C6—C1	1.3905 (18)
O4—N1	1.2231 (15)	C3—C4	1.384 (2)
O3—N1	1.2159 (14)	C17—C18	1.378 (2)
N2—C11	1.3361 (17)	C22—C26	1.3914 (19)
N2—C7	1.3406 (18)	C22—C23	1.3955 (19)
N1—C1	1.4669 (16)	C22—C20	1.4829 (17)
N3—C16	1.3373 (19)	C23—C24	1.3850 (19)
N3—C13	1.3408 (18)	C18—C19	1.3811 (18)
N4—C21	1.3405 (16)	C20—C21	1.3925 (18)
N4—C17	1.3419 (17)	C20—C19	1.3949 (18)
C7—C8	1.3847 (19)	C12—C13	1.3940 (19)
N5—C25	1.3367 (19)	C12—C14	1.3949 (18)
N5—C26	1.3383 (17)	C12—C10	1.4796 (18)
C2—C3	1.3895 (18)	C14—C15	1.384 (2)
C2—C1	1.3913 (17)	C10—C9	1.3929 (19)
C5—C4	1.3859 (19)	C10—C11	1.3932 (18)
C5—C6	1.3954 (18)	C16—C15	1.377 (2)
C8—C9	1.3851 (19)
C11—N2—C7	117.82 (11)	C21—C20—C19	117.00 (12)
O3—N1—O4	123.75 (12)	C21—C20—C22	121.34 (12)
O3—N1—C1	118.21 (11)	C19—C20—C22	121.66 (12)
O4—N1—C1	118.02 (10)	C13—C12—C14	117.02 (12)
C16—N3—C13	116.48 (12)	C13—C12—C10	120.95 (12)
C21—N4—C17	117.55 (11)	C14—C12—C10	122.03 (12)
N2—C7—C8	122.26 (13)	C15—C14—C12	119.25 (13)
C25—N5—C26	116.79 (12)	C6—C1—C2	123.66 (12)
O1—C2—C3	124.80 (12)	C6—C1—N1	118.95 (11)
O1—C2—C1	117.02 (11)	C2—C1—N1	117.38 (11)
C3—C2—C1	118.17 (12)	N4—C21—C20	124.14 (12)
C4—C5—C6	119.68 (12)	C9—C10—C11	116.65 (12)
C7—C8—C9	119.20 (13)	C9—C10—C12	122.89 (12)
N5—C25—C24	123.86 (12)	C11—C10—C12	120.45 (12)
O2—C6—C1	117.43 (11)	C18—C19—C20	119.24 (12)
O2—C6—C5	125.41 (12)	N3—C16—C15	123.93 (13)
C1—C6—C5	117.15 (12)	N2—C11—C10	124.43 (12)
C4—C3—C2	118.95 (12)	N5—C26—C22	124.39 (13)
N4—C17—C18	122.47 (12)	C3—C4—C5	122.39 (12)
C26—C22—C23	117.01 (12)	C16—C15—C14	118.77 (13)
C26—C22—C20	121.78 (12)	C8—C9—C10	119.64 (12)
C23—C22—C20	121.20 (12)	C25—C24—C23	118.59 (13)
C24—C23—C22	119.35 (13)	N3—C13—C12	124.55 (13)
C17—C18—C19	119.59 (12)

(7NRES-44BP)

Crystal data

C42H34N8O8	Z = 1
Mr = 778.77	F(000) = 406
Triclinic, P1	Dx = 1.408 Mg m^−3
a = 7.4323 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1138 (12) Å	Cell parameters from 8552 reflections
c = 14.562 (2) Å	θ = 3.0–27.5°
α = 106.397 (7)°	µ = 0.10 mm^−1
β = 103.133 (7)°	T = 150 K
γ = 90.486 (6)°	Block, yellow
V = 918.7 (2) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3376 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.024
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.829, Tmax = 1.000	k = −11→11
9526 measured reflections	l = −18→18
4200 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0807P)^2 + 0.2379P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
4200 reflections	Δρmax = 0.33 e Å^−3
264 parameters	Δρmin = −0.37 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.21704 (15)	0.14715 (12)	0.88284 (9)	0.0252 (3)
H1	0.319935	0.192423	0.897080	0.038*
O2	−0.10204 (15)	−0.34219 (11)	0.74466 (8)	0.0248 (3)
H2	−0.096850	−0.427216	0.707049	0.037*
O3	−0.15821 (16)	−0.08161 (13)	0.90132 (9)	0.0295 (3)
N4	−0.10142 (16)	−0.03893 (13)	0.83987 (9)	0.0186 (3)
O4	−0.17775 (15)	0.05119 (13)	0.79823 (9)	0.0284 (3)
C20	0.0598 (2)	−0.25839 (16)	0.76464 (11)	0.0194 (3)
C24	0.2264 (2)	−0.00238 (16)	0.83693 (11)	0.0198 (3)
C21	0.2204 (2)	−0.31727 (17)	0.73899 (12)	0.0246 (3)
H21	0.220309	−0.420693	0.705750	0.029*
N1	0.54938 (18)	0.30714 (15)	0.93048 (10)	0.0253 (3)
C16	0.9057 (2)	0.45992 (16)	0.98543 (10)	0.0199 (3)
C19	0.06763 (19)	−0.10135 (16)	0.81344 (11)	0.0180 (3)
C23	0.3858 (2)	−0.06496 (18)	0.81172 (12)	0.0249 (3)
H23	0.494929	−0.002944	0.827173	0.030*
C22	0.3799 (2)	−0.22061 (19)	0.76339 (13)	0.0272 (4)
H22	0.486486	−0.261309	0.746840	0.033*
C14	0.5828 (2)	0.43088 (19)	0.90304 (12)	0.0284 (4)
H14	0.484398	0.465825	0.864840	0.034*
C17	0.8703 (2)	0.33113 (18)	1.01360 (12)	0.0254 (3)
H17	0.965929	0.292811	1.051418	0.030*
C15	0.7546 (2)	0.50992 (19)	0.92796 (13)	0.0277 (4)
H15	0.769851	0.595460	0.906852	0.033*
C18	0.6935 (2)	0.25988 (18)	0.98557 (13)	0.0282 (4)
H18	0.673564	0.174568	1.006083	0.034*
N3	0.0849 (2)	0.62517 (14)	0.36843 (11)	0.0289 (3)
C1	0.0862 (2)	0.81472 (17)	0.52020 (12)	0.0256 (3)
H1A	0.111178	0.840348	0.588598	0.031*
C6	0.0181 (2)	0.92136 (15)	0.47266 (11)	0.0208 (3)
C7	0.4756 (2)	1.08148 (17)	0.51344 (12)	0.0233 (3)
N2	0.3854 (2)	1.38947 (17)	0.56473 (12)	0.0370 (4)
C12	0.4143 (3)	1.15596 (19)	0.44372 (13)	0.0343 (4)
H12	0.401119	1.104982	0.377235	0.041*
C2	0.1174 (2)	0.66986 (17)	0.46629 (13)	0.0277 (4)
H2A	0.163354	0.600342	0.500164	0.033*
C11	0.3720 (3)	1.3080 (2)	0.47285 (15)	0.0383 (4)
H11	0.331262	1.355318	0.423856	0.046*
C4	0.0213 (4)	0.7274 (2)	0.32252 (15)	0.0535 (6)
H4	−0.001496	0.698725	0.254109	0.064*
C8	0.4930 (4)	1.1663 (3)	0.61003 (15)	0.0623 (8)
H8	0.535663	1.122823	0.660800	0.075*
C5	−0.0132 (4)	0.8747 (2)	0.37083 (14)	0.0517 (6)
H5	−0.057295	0.942143	0.334993	0.062*
C9	0.4463 (4)	1.3175 (3)	0.63100 (16)	0.0680 (8)
H9	0.459066	1.371918	0.696893	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0182 (6)	0.0186 (5)	0.0343 (6)	−0.0017 (4)	0.0061 (5)	0.0008 (4)
O2	0.0243 (6)	0.0168 (5)	0.0297 (6)	−0.0010 (4)	0.0085 (5)	−0.0002 (4)
O3	0.0283 (6)	0.0330 (6)	0.0353 (7)	0.0068 (5)	0.0182 (5)	0.0140 (5)
N4	0.0147 (6)	0.0175 (6)	0.0212 (6)	0.0010 (5)	0.0037 (5)	0.0026 (5)
O4	0.0222 (6)	0.0309 (6)	0.0366 (7)	0.0109 (5)	0.0076 (5)	0.0160 (5)
C20	0.0210 (8)	0.0185 (7)	0.0189 (7)	0.0027 (6)	0.0046 (6)	0.0059 (5)
C24	0.0182 (7)	0.0204 (7)	0.0204 (7)	0.0020 (6)	0.0040 (6)	0.0056 (6)
C21	0.0270 (8)	0.0207 (7)	0.0265 (8)	0.0081 (6)	0.0098 (7)	0.0048 (6)
N1	0.0209 (7)	0.0250 (6)	0.0258 (7)	−0.0032 (5)	0.0058 (6)	0.0008 (5)
C16	0.0210 (8)	0.0213 (7)	0.0166 (7)	0.0011 (6)	0.0055 (6)	0.0034 (6)
C19	0.0152 (7)	0.0199 (7)	0.0192 (7)	0.0039 (5)	0.0051 (6)	0.0055 (5)
C23	0.0142 (7)	0.0298 (8)	0.0302 (8)	0.0011 (6)	0.0065 (6)	0.0072 (6)
C22	0.0217 (8)	0.0315 (8)	0.0316 (8)	0.0111 (6)	0.0117 (7)	0.0096 (7)
C14	0.0204 (8)	0.0340 (8)	0.0278 (8)	0.0000 (6)	0.0000 (7)	0.0093 (7)
C17	0.0218 (8)	0.0265 (8)	0.0283 (8)	−0.0001 (6)	0.0028 (7)	0.0113 (6)
C15	0.0242 (8)	0.0307 (8)	0.0298 (8)	−0.0007 (6)	0.0016 (7)	0.0152 (7)
C18	0.0274 (9)	0.0246 (8)	0.0332 (9)	−0.0019 (6)	0.0068 (7)	0.0098 (7)
N3	0.0347 (8)	0.0171 (6)	0.0330 (8)	0.0028 (5)	0.0102 (6)	0.0026 (5)
C1	0.0317 (9)	0.0211 (7)	0.0230 (8)	0.0063 (6)	0.0041 (7)	0.0068 (6)
C6	0.0237 (8)	0.0157 (7)	0.0233 (7)	0.0025 (6)	0.0070 (6)	0.0052 (6)
C7	0.0166 (7)	0.0260 (8)	0.0279 (8)	0.0031 (6)	0.0061 (6)	0.0080 (6)
N2	0.0380 (9)	0.0292 (7)	0.0429 (9)	0.0115 (6)	0.0102 (7)	0.0084 (7)
C12	0.0462 (11)	0.0276 (8)	0.0268 (9)	0.0054 (8)	0.0052 (8)	0.0071 (7)
C2	0.0312 (9)	0.0190 (7)	0.0331 (9)	0.0058 (6)	0.0071 (7)	0.0085 (6)
C11	0.0476 (11)	0.0292 (9)	0.0384 (10)	0.0101 (8)	0.0056 (9)	0.0140 (8)
C4	0.105 (2)	0.0294 (9)	0.0247 (9)	0.0249 (11)	0.0170 (11)	0.0042 (8)
C8	0.120 (2)	0.0444 (12)	0.0273 (10)	0.0459 (14)	0.0207 (12)	0.0142 (9)
C5	0.105 (2)	0.0269 (9)	0.0246 (9)	0.0272 (11)	0.0142 (11)	0.0094 (7)
C9	0.125 (2)	0.0471 (13)	0.0298 (11)	0.0469 (15)	0.0198 (13)	0.0059 (9)

Geometric parameters (Å, º)

O1—C24	1.3482 (17)	C14—C15	1.381 (2)
O2—C20	1.3473 (18)	C17—C18	1.381 (2)
O3—N4	1.2229 (17)	N3—C4	1.325 (2)
N4—O4	1.2234 (16)	N3—C2	1.330 (2)
N4—C19	1.4692 (17)	C1—C6	1.382 (2)
C20—C21	1.397 (2)	C1—C2	1.384 (2)
C20—C19	1.4009 (19)	C6—C5	1.385 (2)
C24—C19	1.396 (2)	C6—C6^ii	1.490 (3)
C24—C23	1.398 (2)	C7—C12	1.372 (2)
C21—C22	1.386 (2)	C7—C8	1.376 (2)
N1—C14	1.337 (2)	C7—C7^iii	1.495 (3)
N1—C18	1.337 (2)	N2—C11	1.315 (2)
C16—C17	1.390 (2)	N2—C9	1.315 (3)
C16—C15	1.403 (2)	C12—C11	1.391 (2)
C16—C16^i	1.488 (3)	C4—C5	1.384 (2)
C23—C22	1.390 (2)	C8—C9	1.390 (3)
O3—N4—O4	124.08 (12)	C18—C17—C16	120.15 (15)
O3—N4—C19	117.95 (12)	C14—C15—C16	119.34 (15)
O4—N4—C19	117.96 (12)	N1—C18—C17	123.44 (15)
O2—C20—C21	124.38 (13)	C4—N3—C2	116.85 (14)
O2—C20—C19	117.99 (12)	C6—C1—C2	120.17 (15)
C21—C20—C19	117.63 (13)	C1—C6—C5	116.28 (14)
O1—C24—C19	118.12 (12)	C1—C6—C6^ii	122.20 (17)
O1—C24—C23	124.08 (14)	C5—C6—C6^ii	121.52 (17)
C19—C24—C23	117.80 (13)	C12—C7—C8	116.15 (15)
C22—C21—C20	119.59 (14)	C12—C7—C7^iii	122.13 (18)
C14—N1—C18	116.63 (14)	C8—C7—C7^iii	121.71 (19)
C17—C16—C15	116.45 (14)	C11—N2—C9	115.06 (15)
C17—C16—C16^i	121.67 (17)	C7—C12—C11	119.76 (16)
C15—C16—C16^i	121.88 (17)	N3—C2—C1	123.24 (15)
C24—C19—C20	123.30 (13)	N2—C11—C12	124.66 (17)
C24—C19—N4	118.95 (12)	N3—C4—C5	123.56 (17)
C20—C19—N4	117.74 (12)	C7—C8—C9	119.39 (19)
C22—C23—C24	119.42 (14)	C4—C5—C6	119.90 (17)
C21—C22—C23	122.24 (14)	N2—C9—C8	124.97 (19)
N1—C14—C15	123.98 (16)

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+2, −z+1.

(8NRES-DPE-I)

Crystal data

C18H17N3O4	F(000) = 712
Mr = 339.34	Dx = 1.337 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 17.802 (3) Å	Cell parameters from 13038 reflections
b = 7.5355 (11) Å	θ = 3.1–27.7°
c = 12.5671 (19) Å	µ = 0.10 mm^−1
β = 91.187 (6)°	T = 150 K
V = 1685.5 (4) Å^3	Block, yellow
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2673 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.074
profile data from ω–scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −23→23
Tmin = 0.752, Tmax = 1.000	k = −9→9
16334 measured reflections	l = −16→16
3859 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.074	H-atom parameters constrained
wR(F^2) = 0.199	w = 1/[σ^2(Fo^2) + (0.0721P)^2 + 1.9128P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
3859 reflections	Δρmax = 0.51 e Å^−3
228 parameters	Δρmin = −0.40 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O2	0.83534 (12)	0.1880 (3)	0.77910 (16)	0.0330 (5)
H2	0.860190	0.277402	0.791915	0.050*
O1	0.66069 (13)	−0.0619 (3)	0.53742 (17)	0.0393 (6)
H1	0.635883	−0.041637	0.483071	0.059*
O4	0.70962 (13)	−0.0781 (3)	0.80485 (17)	0.0406 (6)
O3	0.77914 (14)	−0.2170 (3)	0.6928 (2)	0.0478 (6)
N3	0.74516 (14)	−0.0852 (3)	0.72221 (19)	0.0287 (5)
N2	0.90735 (15)	0.4803 (3)	0.8462 (2)	0.0349 (6)
N1	0.58340 (14)	−0.0297 (4)	0.3534 (2)	0.0334 (6)
C6	0.79470 (15)	0.2120 (4)	0.6882 (2)	0.0261 (6)
C1	0.74767 (15)	0.0740 (4)	0.6550 (2)	0.0253 (6)
C2	0.70453 (16)	0.0795 (4)	0.5608 (2)	0.0284 (6)
C11	0.96895 (17)	0.7614 (4)	0.9644 (2)	0.0303 (6)
C7	0.98037 (18)	0.5232 (4)	0.8398 (2)	0.0326 (7)
H7	1.010590	0.456860	0.795306	0.039*
C5	0.79792 (16)	0.3626 (4)	0.6242 (2)	0.0308 (6)
H5	0.827660	0.458504	0.644898	0.037*
C10	1.01236 (16)	0.6613 (4)	0.8965 (2)	0.0312 (6)
H10	1.063061	0.687326	0.889239	0.037*
C3	0.71006 (16)	0.2306 (4)	0.4967 (2)	0.0309 (6)
H3	0.682919	0.238397	0.432811	0.037*
C4	0.75657 (17)	0.3687 (4)	0.5297 (2)	0.0322 (7)
H4	0.760119	0.468862	0.486811	0.039*
C13	0.62871 (18)	−0.0466 (4)	0.2708 (2)	0.0348 (7)
H13	0.680331	−0.046144	0.283739	0.042*
C9	0.89352 (18)	0.7174 (4)	0.9702 (3)	0.0376 (7)
H9	0.862006	0.781271	1.014196	0.045*
C12	1.00254 (19)	0.9110 (4)	1.0297 (2)	0.0359 (7)
H12A	1.054809	0.884529	1.046306	0.043*
H12B	0.976215	0.920443	1.096293	0.043*
C14	0.50914 (18)	−0.0266 (4)	0.3326 (3)	0.0375 (7)
H14	0.476569	−0.014994	0.389125	0.045*
C17	0.52625 (19)	−0.0622 (4)	0.1450 (3)	0.0381 (8)
C8	0.86558 (18)	0.5780 (5)	0.9100 (3)	0.0405 (8)
H8	0.814754	0.551033	0.914374	0.049*
C15	0.60292 (18)	−0.0646 (5)	0.1674 (3)	0.0394 (8)
H15	0.636789	−0.078255	0.112661	0.047*
C16	0.47917 (18)	−0.0401 (4)	0.2306 (3)	0.0395 (8)
H16	0.427427	−0.034386	0.219380	0.047*
C18	0.4975 (3)	−0.0832 (5)	0.0314 (3)	0.0561 (11)
H18A	0.526368	−0.175011	−0.003218	0.067*
H18B	0.445531	−0.121759	0.032196	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0394 (12)	0.0294 (11)	0.0299 (11)	−0.0083 (9)	−0.0114 (9)	0.0000 (9)
O1	0.0474 (13)	0.0394 (13)	0.0305 (11)	−0.0143 (10)	−0.0137 (10)	0.0019 (10)
O4	0.0520 (13)	0.0449 (14)	0.0252 (11)	−0.0102 (11)	0.0048 (10)	0.0008 (10)
O3	0.0630 (16)	0.0295 (12)	0.0512 (15)	0.0079 (11)	0.0096 (12)	0.0048 (11)
N3	0.0334 (12)	0.0273 (13)	0.0252 (12)	−0.0064 (10)	−0.0044 (10)	−0.0007 (10)
N2	0.0452 (15)	0.0277 (13)	0.0314 (13)	−0.0085 (11)	−0.0088 (11)	0.0007 (11)
N1	0.0376 (14)	0.0350 (14)	0.0273 (13)	0.0009 (11)	−0.0067 (10)	−0.0039 (11)
C6	0.0276 (13)	0.0268 (14)	0.0239 (13)	−0.0002 (11)	−0.0008 (11)	−0.0030 (11)
C1	0.0282 (13)	0.0237 (14)	0.0240 (13)	−0.0003 (11)	−0.0001 (11)	−0.0007 (11)
C2	0.0304 (14)	0.0294 (15)	0.0253 (14)	−0.0015 (12)	−0.0002 (11)	−0.0045 (12)
C11	0.0404 (16)	0.0240 (14)	0.0261 (14)	−0.0033 (12)	−0.0060 (12)	0.0022 (11)
C7	0.0417 (17)	0.0310 (16)	0.0249 (14)	−0.0026 (13)	0.0007 (12)	−0.0003 (12)
C5	0.0325 (15)	0.0250 (14)	0.0348 (16)	−0.0026 (12)	−0.0022 (12)	−0.0007 (12)
C10	0.0300 (14)	0.0312 (15)	0.0323 (15)	−0.0069 (12)	0.0008 (12)	0.0026 (12)
C3	0.0317 (14)	0.0361 (16)	0.0246 (14)	0.0053 (13)	−0.0053 (11)	0.0008 (12)
C4	0.0381 (16)	0.0283 (15)	0.0304 (15)	0.0046 (13)	0.0009 (12)	0.0040 (12)
C13	0.0341 (15)	0.0346 (17)	0.0354 (17)	0.0026 (13)	−0.0076 (13)	−0.0004 (13)
C9	0.0370 (16)	0.0350 (17)	0.0409 (18)	−0.0015 (13)	0.0016 (14)	−0.0067 (14)
C12	0.0493 (18)	0.0264 (16)	0.0317 (16)	−0.0069 (14)	−0.0089 (14)	−0.0009 (13)
C14	0.0386 (17)	0.0398 (18)	0.0341 (16)	0.0004 (14)	0.0025 (13)	−0.0050 (14)
C17	0.0493 (18)	0.0334 (17)	0.0312 (16)	−0.0114 (14)	−0.0127 (14)	0.0065 (13)
C8	0.0321 (16)	0.0434 (19)	0.0460 (19)	−0.0077 (14)	−0.0015 (14)	−0.0006 (15)
C15	0.0427 (17)	0.0451 (19)	0.0304 (16)	−0.0050 (15)	0.0000 (13)	0.0001 (14)
C16	0.0340 (16)	0.0370 (17)	0.0470 (19)	−0.0024 (14)	−0.0148 (14)	0.0033 (15)
C18	0.075 (3)	0.053 (2)	0.039 (2)	−0.024 (2)	−0.0249 (19)	0.0108 (17)

Geometric parameters (Å, º)

O2—C6	1.352 (3)	C10—H10	0.9300
O2—H2	0.8200	C3—C4	1.388 (4)
O1—C2	1.350 (4)	C3—H3	0.9300
O1—H1	0.8200	C4—H4	0.9300
O4—N3	1.228 (3)	C13—C15	1.376 (4)
O3—N3	1.224 (3)	C13—H13	0.9300
N3—C1	1.469 (4)	C9—C8	1.382 (5)
N2—C8	1.328 (4)	C9—H9	0.9300
N2—C7	1.343 (4)	C12—C12^i	1.537 (6)
N1—C13	1.334 (4)	C12—H12A	0.9700
N1—C14	1.342 (4)	C12—H12B	0.9700
C6—C5	1.392 (4)	C14—C16	1.382 (5)
C6—C1	1.394 (4)	C14—H14	0.9300
C1—C2	1.398 (4)	C17—C16	1.388 (5)
C2—C3	1.400 (4)	C17—C15	1.388 (5)
C11—C10	1.386 (4)	C17—C18	1.514 (4)
C11—C9	1.386 (4)	C8—H8	0.9300
C11—C12	1.511 (4)	C15—H15	0.9300
C7—C10	1.378 (4)	C16—H16	0.9300
C7—H7	0.9300	C18—C18^ii	1.486 (7)
C5—C4	1.386 (4)	C18—H18A	0.9700
C5—H5	0.9300	C18—H18B	0.9700
C6—O2—H2	109.5	N1—C13—C15	123.3 (3)
C2—O1—H1	109.5	N1—C13—H13	118.3
O3—N3—O4	123.9 (3)	C15—C13—H13	118.3
O3—N3—C1	117.9 (2)	C8—C9—C11	119.4 (3)
O4—N3—C1	118.2 (2)	C8—C9—H9	120.3
C8—N2—C7	117.2 (3)	C11—C9—H9	120.3
C13—N1—C14	117.3 (3)	C11—C12—C12^i	111.6 (3)
O2—C6—C5	124.7 (2)	C11—C12—H12A	109.3
O2—C6—C1	117.5 (2)	C12^i—C12—H12A	109.3
C5—C6—C1	117.8 (2)	C11—C12—H12B	109.3
C6—C1—C2	123.2 (3)	C12^i—C12—H12B	109.3
C6—C1—N3	117.5 (2)	H12A—C12—H12B	108.0
C2—C1—N3	119.2 (2)	N1—C14—C16	122.6 (3)
O1—C2—C1	117.8 (3)	N1—C14—H14	118.7
O1—C2—C3	124.3 (3)	C16—C14—H14	118.7
C1—C2—C3	117.9 (3)	C16—C17—C15	116.8 (3)
C10—C11—C9	117.1 (3)	C16—C17—C18	123.1 (3)
C10—C11—C12	121.4 (3)	C15—C17—C18	120.1 (3)
C9—C11—C12	121.5 (3)	N2—C8—C9	123.6 (3)
N2—C7—C10	122.8 (3)	N2—C8—H8	118.2
N2—C7—H7	118.6	C9—C8—H8	118.2
C10—C7—H7	118.6	C13—C15—C17	119.9 (3)
C4—C5—C6	119.7 (3)	C13—C15—H15	120.1
C4—C5—H5	120.2	C17—C15—H15	120.1
C6—C5—H5	120.2	C14—C16—C17	120.0 (3)
C7—C10—C11	120.0 (3)	C14—C16—H16	120.0
C7—C10—H10	120.0	C17—C16—H16	120.0
C11—C10—H10	120.0	C18^ii—C18—C17	112.9 (4)
C4—C3—C2	119.1 (3)	C18^ii—C18—H18A	109.0
C4—C3—H3	120.4	C17—C18—H18A	109.0
C2—C3—H3	120.4	C18^ii—C18—H18B	109.0
C5—C4—C3	122.3 (3)	C17—C18—H18B	109.0
C5—C4—H4	118.9	H18A—C18—H18B	107.8
C3—C4—H4	118.9

Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+1, −y, −z.

(9NRES-DPE-II)

Crystal data

C18H15N3O4	F(000) = 704
Mr = 337.33	Dx = 1.385 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 17.9122 (13) Å	Cell parameters from 13763 reflections
b = 7.4259 (5) Å	θ = 3.2–27.6°
c = 12.1765 (8) Å	µ = 0.10 mm^−1
β = 92.337 (7)°	T = 150 K
V = 1618.30 (19) Å^3	Block, yellow
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2933 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.040
profile data from ω–scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −23→23
Tmin = 0.818, Tmax = 1.000	k = −9→9
16284 measured reflections	l = −15→15
3707 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0487P)^2 + 0.5466P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3707 reflections	Δρmax = 0.25 e Å^−3
236 parameters	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O001	0.84598 (6)	0.14176 (14)	0.79383 (8)	0.0263 (3)
H001	0.870566	0.232785	0.807436	0.039*
O002	0.65923 (6)	−0.10196 (14)	0.55885 (8)	0.0265 (3)
H002	0.633943	−0.083770	0.502280	0.040*
O003	0.71992 (6)	−0.12122 (15)	0.82946 (8)	0.0322 (3)
O004	0.78070 (7)	−0.26443 (15)	0.70767 (10)	0.0378 (3)
N3	0.75081 (7)	−0.12920 (16)	0.74151 (10)	0.0225 (3)
N1	0.91348 (7)	0.44416 (17)	0.86049 (10)	0.0249 (3)
N2	0.57684 (7)	−0.05617 (18)	0.37171 (10)	0.0257 (3)
C2	0.70284 (8)	0.04221 (19)	0.58097 (11)	0.0200 (3)
C1	0.75126 (8)	0.03328 (18)	0.67354 (11)	0.0192 (3)
C6	0.79998 (8)	0.17128 (19)	0.70537 (11)	0.0201 (3)
C11	0.94985 (8)	0.7850 (2)	0.94646 (11)	0.0225 (3)
C3	0.70334 (8)	0.1996 (2)	0.51904 (11)	0.0235 (3)
H3	0.671866	0.211037	0.456779	0.028*
C17	0.51532 (8)	−0.02266 (19)	0.15729 (11)	0.0219 (3)
C5	0.79905 (8)	0.32735 (19)	0.64239 (12)	0.0227 (3)
H5	0.830423	0.423021	0.661677	0.027*
C4	0.75089 (8)	0.3393 (2)	0.55045 (12)	0.0242 (3)
H4	0.750515	0.444101	0.508661	0.029*
C18	0.48157 (8)	−0.0022 (2)	0.04614 (12)	0.0249 (3)
C13	0.61992 (8)	−0.0417 (2)	0.28507 (12)	0.0247 (3)
H13	0.671487	−0.041738	0.297632	0.030*
C15	0.59230 (8)	−0.0269 (2)	0.17836 (12)	0.0251 (3)
H15	0.624753	−0.019816	0.120807	0.030*
C10	1.00089 (8)	0.6850 (2)	0.88797 (12)	0.0250 (3)
H10	1.048293	0.730747	0.876681	0.030*
C16	0.47049 (8)	−0.0365 (2)	0.24730 (12)	0.0265 (3)
H16	0.418753	−0.033400	0.237371	0.032*
C7	0.98076 (8)	0.5181 (2)	0.84698 (12)	0.0257 (3)
H7	1.015524	0.453650	0.808090	0.031*
C9	0.88026 (8)	0.7079 (2)	0.96030 (13)	0.0270 (3)
H9	0.844227	0.769146	0.998578	0.032*
C12	0.96634 (9)	0.9640 (2)	0.99265 (12)	0.0251 (3)
C8	0.86502 (8)	0.5400 (2)	0.91682 (13)	0.0280 (3)
H8	0.818162	0.490518	0.927378	0.034*
C14	0.50289 (9)	−0.0549 (2)	0.35165 (12)	0.0285 (3)
H14	0.471852	−0.066920	0.410597	0.034*
H12	0.9231 (10)	1.034 (3)	1.0122 (14)	0.036 (5)*
H18	0.4281 (10)	0.008 (2)	0.0447 (13)	0.030 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O001	0.0305 (6)	0.0203 (5)	0.0273 (5)	−0.0064 (4)	−0.0105 (4)	−0.0001 (4)
O002	0.0302 (6)	0.0258 (6)	0.0227 (5)	−0.0062 (5)	−0.0090 (4)	0.0008 (4)
O003	0.0429 (7)	0.0338 (6)	0.0201 (5)	−0.0103 (5)	0.0030 (5)	0.0014 (5)
O004	0.0538 (8)	0.0202 (6)	0.0397 (7)	0.0082 (5)	0.0047 (6)	0.0019 (5)
N3	0.0263 (6)	0.0192 (6)	0.0215 (6)	−0.0042 (5)	−0.0048 (5)	−0.0001 (5)
N1	0.0260 (6)	0.0223 (6)	0.0260 (6)	−0.0038 (5)	−0.0039 (5)	−0.0015 (5)
N2	0.0263 (7)	0.0298 (7)	0.0206 (6)	0.0016 (5)	−0.0028 (5)	−0.0027 (5)
C2	0.0195 (7)	0.0214 (7)	0.0192 (7)	0.0004 (6)	0.0012 (5)	−0.0033 (6)
C1	0.0219 (7)	0.0168 (7)	0.0188 (7)	0.0007 (6)	0.0017 (5)	−0.0003 (5)
C6	0.0205 (7)	0.0197 (7)	0.0201 (7)	0.0018 (6)	0.0000 (5)	−0.0031 (5)
C11	0.0245 (7)	0.0218 (7)	0.0209 (7)	−0.0030 (6)	−0.0024 (6)	−0.0006 (6)
C3	0.0247 (7)	0.0259 (8)	0.0196 (7)	0.0049 (6)	−0.0015 (6)	0.0012 (6)
C17	0.0240 (7)	0.0222 (7)	0.0192 (7)	−0.0001 (6)	−0.0014 (6)	−0.0018 (6)
C5	0.0228 (7)	0.0172 (7)	0.0284 (8)	−0.0009 (6)	0.0027 (6)	−0.0024 (6)
C4	0.0266 (8)	0.0181 (7)	0.0280 (8)	0.0044 (6)	0.0033 (6)	0.0049 (6)
C18	0.0220 (7)	0.0306 (8)	0.0220 (7)	0.0005 (6)	−0.0019 (6)	−0.0006 (6)
C13	0.0198 (7)	0.0276 (8)	0.0265 (7)	0.0033 (6)	−0.0030 (6)	−0.0026 (6)
C15	0.0230 (7)	0.0303 (8)	0.0221 (7)	0.0008 (6)	0.0021 (6)	−0.0002 (6)
C10	0.0209 (7)	0.0284 (8)	0.0258 (7)	−0.0067 (6)	0.0023 (6)	−0.0034 (6)
C16	0.0200 (7)	0.0363 (9)	0.0231 (7)	0.0008 (6)	−0.0006 (6)	−0.0028 (6)
C7	0.0243 (7)	0.0260 (8)	0.0269 (8)	−0.0008 (6)	0.0002 (6)	−0.0057 (6)
C9	0.0223 (7)	0.0273 (8)	0.0315 (8)	−0.0006 (6)	0.0021 (6)	−0.0056 (7)
C12	0.0253 (7)	0.0239 (8)	0.0260 (7)	−0.0009 (6)	0.0013 (6)	−0.0037 (6)
C8	0.0213 (7)	0.0299 (8)	0.0329 (8)	−0.0073 (6)	0.0002 (6)	−0.0006 (7)
C14	0.0251 (8)	0.0389 (9)	0.0215 (7)	0.0007 (7)	0.0023 (6)	−0.0023 (7)

Geometric parameters (Å, º)

O001—C6	1.3472 (16)	C17—C15	1.393 (2)
O001—H001	0.8200	C17—C18	1.468 (2)
O002—C2	1.3460 (17)	C5—C4	1.388 (2)
O002—H002	0.8200	C5—H5	0.9300
O003—N3	1.2267 (16)	C4—H4	0.9300
O004—N3	1.2178 (16)	C18—C18^i	1.327 (3)
N3—C1	1.4634 (18)	C18—H18	0.960 (17)
N1—C8	1.334 (2)	C13—C15	1.376 (2)
N1—C7	1.3404 (19)	C13—H13	0.9300
N2—C13	1.3366 (19)	C15—H15	0.9300
N2—C14	1.3370 (19)	C10—C7	1.379 (2)
C2—C3	1.391 (2)	C10—H10	0.9300
C2—C1	1.3954 (19)	C16—C14	1.382 (2)
C1—C6	1.391 (2)	C16—H16	0.9300
C6—C5	1.389 (2)	C7—H7	0.9300
C11—C9	1.388 (2)	C9—C8	1.378 (2)
C11—C10	1.396 (2)	C9—H9	0.9300
C11—C12	1.469 (2)	C12—C12^ii	1.325 (3)
C3—C4	1.386 (2)	C12—H12	0.971 (18)
C3—H3	0.9300	C8—H8	0.9300
C17—C16	1.389 (2)	C14—H14	0.9300
C6—O001—H001	109.5	C18^i—C18—C17	125.67 (18)
C2—O002—H002	109.5	C18^i—C18—H18	120.9 (10)
O004—N3—O003	123.74 (13)	C17—C18—H18	113.5 (10)
O004—N3—C1	118.42 (12)	N2—C13—C15	123.70 (13)
O003—N3—C1	117.84 (12)	N2—C13—H13	118.1
C8—N1—C7	116.86 (13)	C15—C13—H13	118.1
C13—N2—C14	117.05 (13)	C13—C15—C17	119.41 (14)
O002—C2—C3	125.18 (12)	C13—C15—H15	120.3
O002—C2—C1	117.41 (12)	C17—C15—H15	120.3
C3—C2—C1	117.41 (13)	C7—C10—C11	119.74 (14)
C6—C1—C2	123.53 (13)	C7—C10—H10	120.1
C6—C1—N3	117.89 (12)	C11—C10—H10	120.1
C2—C1—N3	118.58 (12)	C14—C16—C17	119.89 (14)
O001—C6—C5	124.76 (13)	C14—C16—H16	120.1
O001—C6—C1	117.34 (13)	C17—C16—H16	120.1
C5—C6—C1	117.88 (13)	N1—C7—C10	123.15 (14)
C9—C11—C10	116.92 (13)	N1—C7—H7	118.4
C9—C11—C12	119.61 (14)	C10—C7—H7	118.4
C10—C11—C12	123.47 (13)	C8—C9—C11	119.42 (14)
C4—C3—C2	119.77 (13)	C8—C9—H9	120.3
C4—C3—H3	120.1	C11—C9—H9	120.3
C2—C3—H3	120.1	C12^ii—C12—C11	125.78 (19)
C16—C17—C15	116.94 (13)	C12^ii—C12—H12	118.8 (11)
C16—C17—C18	120.38 (13)	C11—C12—H12	115.4 (11)
C15—C17—C18	122.68 (13)	N1—C8—C9	123.90 (14)
C4—C5—C6	119.43 (13)	N1—C8—H8	118.0
C4—C5—H5	120.3	C9—C8—H8	118.0
C6—C5—H5	120.3	N2—C14—C16	122.99 (14)
C3—C4—C5	121.98 (13)	N2—C14—H14	118.5
C3—C4—H4	119.0	C16—C14—H14	118.5
C5—C4—H4	119.0

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+2, −z+2.

(10NRES-44AZO)

Crystal data

C16H13N5O4	F(000) = 704
Mr = 339.31	Dx = 1.422 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 18.213 (3) Å	Cell parameters from 12104 reflections
b = 7.2967 (13) Å	θ = 3.0–27.6°
c = 11.940 (2) Å	µ = 0.11 mm^−1
β = 92.967 (7)°	T = 150 K
V = 1584.7 (5) Å^3	Block, red
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2782 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.054
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −23→23
Tmin = 0.686, Tmax = 1.000	k = −9→9
14469 measured reflections	l = −15→15
3639 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0606P)^2 + 1.0262P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3639 reflections	Δρmax = 0.69 e Å^−3
228 parameters	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.14931 (8)	0.1420 (2)	0.20812 (12)	0.0332 (4)
H1	0.125878	0.235681	0.193280	0.050*
O2	0.34443 (8)	−0.0912 (2)	0.43735 (12)	0.0355 (4)
H2	0.366096	−0.078145	0.498750	0.053*
O3	0.28655 (10)	−0.1186 (2)	0.17188 (13)	0.0467 (4)
N5	0.24990 (10)	−0.1257 (2)	0.25486 (14)	0.0315 (4)
O4	0.21592 (11)	−0.2609 (2)	0.28178 (16)	0.0527 (5)
N2	0.08673 (9)	0.4601 (2)	0.13670 (15)	0.0308 (4)
N1	0.42295 (10)	−0.0529 (2)	0.63618 (14)	0.0327 (4)
N3	0.51978 (10)	−0.0326 (3)	0.96381 (14)	0.0336 (4)
N4	0.02702 (9)	0.9600 (2)	−0.01889 (15)	0.0328 (4)
C2	0.19633 (11)	0.1729 (3)	0.29705 (16)	0.0262 (4)
C1	0.24772 (11)	0.0378 (3)	0.32621 (16)	0.0260 (4)
C6	0.29771 (10)	0.0504 (3)	0.41804 (16)	0.0270 (4)
C15	0.48363 (11)	−0.0370 (3)	0.85373 (17)	0.0297 (4)
C16	0.40835 (12)	−0.0288 (3)	0.83389 (18)	0.0321 (5)
H16	0.377159	−0.018648	0.892838	0.039*
C5	0.29578 (11)	0.2091 (3)	0.48352 (17)	0.0301 (4)
H5	0.328252	0.222838	0.545650	0.036*
C11	0.04509 (11)	0.7909 (3)	0.03891 (17)	0.0296 (4)
C3	0.19550 (11)	0.3302 (3)	0.36400 (18)	0.0301 (4)
H3	0.161904	0.423501	0.347387	0.036*
C4	0.24534 (11)	0.3454 (3)	0.45548 (18)	0.0322 (5)
H4	0.244818	0.450709	0.499326	0.039*
C12	0.38071 (12)	−0.0361 (3)	0.72449 (18)	0.0332 (5)
H12	0.330040	−0.029003	0.711010	0.040*
C9	−0.00082 (11)	0.7028 (3)	0.10984 (18)	0.0318 (5)
H9	−0.046103	0.753017	0.125421	0.038*
C14	0.52882 (12)	−0.0556 (3)	0.76363 (18)	0.0338 (5)
H14	0.579633	−0.063069	0.775031	0.041*
C13	0.49569 (12)	−0.0625 (3)	0.65663 (18)	0.0351 (5)
H13	0.525501	−0.074499	0.596127	0.042*
C8	0.02203 (12)	0.5383 (3)	0.15724 (18)	0.0338 (5)
H8	−0.008730	0.479178	0.205452	0.041*
C7	0.13056 (12)	0.5487 (3)	0.0683 (2)	0.0354 (5)
H7	0.175848	0.496890	0.054374	0.042*
C10	0.11191 (12)	0.7128 (3)	0.01741 (19)	0.0365 (5)
H10	0.143620	0.769674	−0.030330	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0379 (8)	0.0255 (7)	0.0349 (8)	0.0070 (6)	−0.0103 (6)	−0.0001 (6)
O2	0.0384 (8)	0.0384 (9)	0.0288 (8)	0.0107 (7)	−0.0082 (6)	−0.0016 (6)
O3	0.0650 (11)	0.0457 (10)	0.0299 (9)	0.0174 (9)	0.0089 (8)	0.0015 (7)
N5	0.0379 (10)	0.0297 (9)	0.0262 (9)	0.0067 (8)	−0.0052 (7)	−0.0008 (7)
O4	0.0689 (12)	0.0306 (9)	0.0596 (12)	−0.0140 (9)	0.0130 (9)	−0.0109 (8)
N2	0.0340 (9)	0.0245 (9)	0.0333 (9)	0.0033 (7)	−0.0051 (7)	−0.0002 (7)
N1	0.0351 (9)	0.0336 (10)	0.0287 (9)	−0.0029 (8)	−0.0038 (7)	0.0030 (7)
N3	0.0356 (10)	0.0373 (10)	0.0276 (9)	0.0043 (8)	−0.0021 (7)	0.0007 (7)
N4	0.0325 (9)	0.0270 (9)	0.0388 (10)	0.0059 (7)	0.0015 (7)	0.0018 (7)
C2	0.0286 (10)	0.0233 (10)	0.0267 (10)	−0.0019 (8)	0.0001 (7)	0.0028 (7)
C1	0.0295 (10)	0.0238 (10)	0.0246 (10)	0.0007 (8)	0.0004 (7)	−0.0009 (7)
C6	0.0269 (10)	0.0297 (11)	0.0244 (10)	−0.0013 (8)	0.0014 (7)	0.0015 (8)
C15	0.0343 (11)	0.0272 (10)	0.0271 (10)	0.0006 (9)	−0.0018 (8)	0.0022 (8)
C16	0.0342 (11)	0.0307 (11)	0.0317 (11)	−0.0016 (9)	0.0035 (8)	0.0012 (8)
C5	0.0312 (10)	0.0311 (11)	0.0277 (10)	−0.0051 (9)	−0.0024 (8)	−0.0005 (8)
C11	0.0338 (11)	0.0217 (10)	0.0328 (11)	0.0024 (8)	−0.0031 (8)	−0.0020 (8)
C3	0.0317 (10)	0.0208 (10)	0.0376 (11)	0.0005 (8)	0.0005 (8)	0.0003 (8)
C4	0.0364 (11)	0.0251 (10)	0.0352 (11)	−0.0061 (9)	0.0029 (8)	−0.0055 (8)
C12	0.0302 (10)	0.0333 (12)	0.0358 (12)	−0.0045 (9)	−0.0021 (8)	0.0027 (9)
C9	0.0309 (10)	0.0285 (11)	0.0358 (11)	0.0065 (9)	0.0008 (8)	−0.0003 (8)
C14	0.0310 (10)	0.0396 (13)	0.0304 (11)	0.0031 (9)	−0.0005 (8)	0.0015 (9)
C13	0.0363 (11)	0.0420 (13)	0.0270 (11)	−0.0001 (10)	0.0020 (8)	0.0026 (9)
C8	0.0349 (11)	0.0321 (11)	0.0345 (11)	0.0046 (9)	0.0019 (8)	0.0062 (9)
C7	0.0286 (10)	0.0309 (12)	0.0467 (13)	0.0070 (9)	0.0023 (9)	−0.0018 (9)
C10	0.0342 (11)	0.0324 (11)	0.0431 (13)	0.0019 (9)	0.0053 (9)	0.0044 (9)

Geometric parameters (Å, º)

O1—C2	1.348 (2)	C15—C14	1.395 (3)
O1—H1	0.8200	C16—C12	1.376 (3)
O2—C6	1.351 (2)	C16—H16	0.9300
O2—H2	0.8200	C5—C4	1.384 (3)
O3—N5	1.224 (2)	C5—H5	0.9300
N5—O4	1.216 (2)	C11—C9	1.379 (3)
N5—C1	1.468 (3)	C11—C10	1.380 (3)
N2—C7	1.338 (3)	C3—C4	1.388 (3)
N2—C8	1.343 (3)	C3—H3	0.9300
N1—C13	1.337 (3)	C4—H4	0.9300
N1—C12	1.343 (3)	C12—H12	0.9300
N3—N3^i	1.248 (3)	C9—C8	1.382 (3)
N3—C15	1.440 (3)	C9—H9	0.9300
N4—N4^ii	1.249 (3)	C14—C13	1.385 (3)
N4—C11	1.444 (3)	C14—H14	0.9300
C2—C1	1.391 (3)	C13—H13	0.9300
C2—C3	1.399 (3)	C8—H8	0.9300
C1—C6	1.392 (3)	C7—C10	1.377 (3)
C6—C5	1.398 (3)	C7—H7	0.9300
C15—C16	1.381 (3)	C10—H10	0.9300
C2—O1—H1	109.5	C10—C11—N4	116.45 (19)
C6—O2—H2	109.5	C4—C3—C2	119.30 (19)
O4—N5—O3	123.70 (19)	C4—C3—H3	120.4
O4—N5—C1	118.44 (17)	C2—C3—H3	120.4
O3—N5—C1	117.86 (18)	C5—C4—C3	122.12 (19)
C7—N2—C8	117.60 (18)	C5—C4—H4	118.9
C13—N1—C12	117.66 (18)	C3—C4—H4	118.9
N3^i—N3—C15	112.8 (2)	N1—C12—C16	123.55 (19)
N4^ii—N4—C11	113.0 (2)	N1—C12—H12	118.2
O1—C2—C1	118.06 (17)	C16—C12—H12	118.2
O1—C2—C3	124.17 (18)	C11—C9—C8	118.47 (19)
C1—C2—C3	117.74 (18)	C11—C9—H9	120.8
C2—C1—C6	123.68 (18)	C8—C9—H9	120.8
C2—C1—N5	117.97 (17)	C13—C14—C15	117.95 (19)
C6—C1—N5	118.35 (17)	C13—C14—H14	121.0
O2—C6—C1	117.68 (17)	C15—C14—H14	121.0
O2—C6—C5	124.87 (17)	N1—C13—C14	123.1 (2)
C1—C6—C5	117.45 (18)	N1—C13—H13	118.4
C16—C15—C14	119.50 (19)	C14—C13—H13	118.4
C16—C15—N3	123.98 (19)	N2—C8—C9	122.9 (2)
C14—C15—N3	116.50 (18)	N2—C8—H8	118.6
C12—C16—C15	118.18 (19)	C9—C8—H8	118.6
C12—C16—H16	120.9	N2—C7—C10	123.2 (2)
C15—C16—H16	120.9	N2—C7—H7	118.4
C4—C5—C6	119.72 (18)	C10—C7—H7	118.4
C4—C5—H5	120.1	C7—C10—C11	118.5 (2)
C6—C5—H5	120.1	C7—C10—H10	120.8
C9—C11—C10	119.37 (19)	C11—C10—H10	120.8
C9—C11—N4	124.15 (18)

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y+2, −z.

(11NRES-4DMAP)

Crystal data

C20H25N5O4	Z = 2
Mr = 399.45	F(000) = 424
Triclinic, P1	Dx = 1.322 Mg m^−3
a = 7.7563 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1082 (13) Å	Cell parameters from 9048 reflections
c = 16.240 (3) Å	θ = 3.0–27.6°
α = 97.387 (7)°	µ = 0.09 mm^−1
β = 95.164 (7)°	T = 150 K
γ = 95.007 (7)°	Block, brown
V = 1003.7 (3) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3549 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.026
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −10→10
Tmin = 0.863, Tmax = 1.000	k = −10→10
10336 measured reflections	l = −21→21
4570 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.0522P)^2 + 0.7433P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
4570 reflections	Δρmax = 0.36 e Å^−3
264 parameters	Δρmin = −0.36 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O4	0.60341 (17)	0.02852 (17)	0.16535 (9)	0.0287 (3)
H4	0.630681	−0.055872	0.138149	0.043*
O1	0.50221 (19)	0.43882 (17)	0.24905 (9)	0.0350 (4)
N1	0.5560 (2)	0.31112 (19)	0.27075 (9)	0.0236 (3)
N3	0.6784 (2)	0.7554 (2)	1.07806 (11)	0.0308 (4)
O3	0.83865 (19)	0.51870 (18)	0.34057 (10)	0.0380 (4)
H3	0.929951	0.576277	0.358113	0.057*
N2	0.7794 (2)	0.31238 (19)	0.93565 (10)	0.0256 (3)
C6	0.7478 (2)	0.1239 (2)	0.20101 (11)	0.0212 (4)
O2	0.47029 (19)	0.2152 (2)	0.30746 (10)	0.0389 (4)
C10	0.6845 (2)	0.5902 (2)	0.94444 (12)	0.0261 (4)
H10	0.663863	0.581947	0.886679	0.031*
C3	1.0388 (2)	0.3430 (2)	0.27584 (12)	0.0257 (4)
H3A	1.136288	0.413507	0.299944	0.031*
C1	0.7303 (2)	0.2721 (2)	0.25282 (10)	0.0200 (4)
C11	0.7526 (2)	0.4583 (2)	0.98166 (11)	0.0222 (4)
C2	0.8724 (2)	0.3844 (2)	0.29101 (11)	0.0234 (4)
C4	1.0583 (3)	0.1971 (2)	0.22495 (12)	0.0277 (4)
H4A	1.169804	0.171106	0.215356	0.033*
C8	0.6490 (3)	0.7307 (2)	0.99419 (13)	0.0286 (4)
H8	0.601479	0.814547	0.968222	0.034*
C5	0.9167 (3)	0.0879 (2)	0.18762 (12)	0.0273 (4)
H5	0.934373	−0.009250	0.153650	0.033*
C9	0.7880 (2)	0.4862 (2)	1.06950 (12)	0.0268 (4)
H9	0.837720	0.406161	1.097518	0.032*
C7	0.7484 (3)	0.6320 (3)	1.11318 (12)	0.0299 (4)
H7	0.771657	0.646531	1.170982	0.036*
C12	0.8386 (3)	0.1750 (3)	0.97629 (14)	0.0339 (5)
H12A	0.850695	0.082250	0.934803	0.051*
H12B	0.948981	0.210303	1.008124	0.051*
H12C	0.755295	0.141676	1.012784	0.051*
C13	0.7482 (3)	0.2896 (3)	0.84495 (12)	0.0336 (5)
H13A	0.773823	0.179703	0.823069	0.050*
H13B	0.628581	0.302381	0.828681	0.050*
H13C	0.821769	0.371645	0.823302	0.050*
N4	0.0777 (2)	0.7367 (2)	0.41400 (11)	0.0322 (4)
N5	0.3475 (2)	1.1630 (2)	0.55655 (11)	0.0347 (4)
C16	0.2623 (2)	1.0245 (2)	0.50966 (13)	0.0279 (4)
C17	0.2203 (4)	0.8794 (3)	0.54327 (17)	0.0655 (10)
H17	0.253032	0.874380	0.599345	0.079*
C15	0.3870 (5)	1.3135 (4)	0.51993 (17)	0.0702 (10)
H15A	0.447237	1.398395	0.561815	0.105*
H15B	0.459126	1.290205	0.475658	0.105*
H15C	0.280782	1.351676	0.497988	0.105*
C14	0.3956 (4)	1.1664 (3)	0.64494 (17)	0.0589 (8)
H14A	0.454592	1.273853	0.667727	0.088*
H14B	0.292850	1.146499	0.672453	0.088*
H14C	0.471400	1.081251	0.653308	0.088*
C20	0.1307 (5)	0.7429 (3)	0.49415 (18)	0.0678 (10)
H20	0.105426	0.647785	0.519041	0.081*
C19	0.1177 (4)	0.8749 (3)	0.38177 (14)	0.0524 (7)
H19	0.082156	0.875515	0.325576	0.063*
C18	0.2075 (4)	1.0174 (3)	0.42506 (14)	0.0587 (8)
H18	0.232110	1.109581	0.397897	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0236 (7)	0.0250 (7)	0.0331 (8)	−0.0016 (5)	0.0006 (5)	−0.0081 (6)
O1	0.0323 (8)	0.0271 (7)	0.0444 (9)	0.0119 (6)	−0.0076 (6)	0.0019 (6)
N1	0.0245 (8)	0.0255 (8)	0.0185 (7)	0.0042 (6)	−0.0037 (6)	−0.0020 (6)
N3	0.0277 (9)	0.0272 (8)	0.0337 (9)	−0.0040 (7)	0.0049 (7)	−0.0073 (7)
O3	0.0289 (8)	0.0304 (8)	0.0464 (9)	0.0042 (6)	−0.0090 (7)	−0.0185 (7)
N2	0.0303 (9)	0.0241 (8)	0.0230 (8)	0.0057 (6)	0.0051 (6)	0.0013 (6)
C6	0.0244 (9)	0.0200 (8)	0.0181 (8)	−0.0004 (7)	0.0009 (7)	0.0014 (6)
O2	0.0297 (8)	0.0508 (9)	0.0423 (9)	0.0107 (7)	0.0125 (7)	0.0183 (7)
C10	0.0278 (10)	0.0262 (9)	0.0226 (9)	−0.0008 (8)	−0.0001 (7)	0.0015 (7)
C3	0.0223 (9)	0.0270 (9)	0.0256 (9)	−0.0030 (7)	−0.0019 (7)	0.0020 (7)
C1	0.0208 (9)	0.0221 (8)	0.0173 (8)	0.0041 (7)	0.0001 (6)	0.0032 (6)
C11	0.0187 (9)	0.0234 (9)	0.0234 (9)	−0.0022 (7)	0.0041 (7)	0.0010 (7)
C2	0.0282 (10)	0.0196 (8)	0.0207 (9)	0.0028 (7)	−0.0033 (7)	−0.0002 (7)
C4	0.0217 (9)	0.0325 (10)	0.0290 (10)	0.0027 (8)	0.0057 (7)	0.0016 (8)
C8	0.0273 (10)	0.0208 (9)	0.0358 (11)	−0.0013 (7)	0.0006 (8)	0.0003 (8)
C5	0.0281 (10)	0.0249 (9)	0.0275 (10)	0.0031 (8)	0.0059 (8)	−0.0042 (7)
C9	0.0257 (10)	0.0296 (10)	0.0239 (9)	−0.0029 (8)	0.0017 (7)	0.0036 (7)
C7	0.0292 (10)	0.0342 (11)	0.0225 (9)	−0.0068 (8)	0.0027 (8)	−0.0035 (8)
C12	0.0387 (12)	0.0283 (10)	0.0369 (11)	0.0075 (9)	0.0092 (9)	0.0059 (8)
C13	0.0409 (12)	0.0336 (11)	0.0248 (10)	0.0042 (9)	0.0056 (8)	−0.0033 (8)
N4	0.0268 (9)	0.0303 (9)	0.0348 (9)	0.0020 (7)	−0.0037 (7)	−0.0087 (7)
N5	0.0290 (9)	0.0302 (9)	0.0392 (10)	−0.0018 (7)	0.0030 (7)	−0.0130 (7)
C16	0.0170 (9)	0.0285 (10)	0.0347 (10)	0.0042 (7)	0.0031 (7)	−0.0104 (8)
C17	0.113 (3)	0.0211 (11)	0.0499 (15)	0.0047 (13)	−0.0536 (16)	0.0006 (10)
C15	0.096 (2)	0.0549 (16)	0.0479 (15)	−0.0504 (16)	0.0369 (15)	−0.0175 (13)
C14	0.0777 (19)	0.0304 (12)	0.0560 (16)	0.0180 (12)	−0.0405 (14)	−0.0168 (11)
C20	0.118 (3)	0.0193 (11)	0.0535 (16)	−0.0030 (13)	−0.0471 (17)	0.0047 (10)
C19	0.0704 (18)	0.0576 (16)	0.0208 (10)	−0.0310 (13)	0.0101 (11)	−0.0051 (10)
C18	0.087 (2)	0.0544 (15)	0.0255 (12)	−0.0436 (15)	0.0177 (12)	−0.0032 (10)

Geometric parameters (Å, º)

O4—C6	1.343 (2)	C3—C2	1.397 (3)
O1—N1	1.230 (2)	C1—C2	1.409 (2)
N1—O2	1.226 (2)	C11—C9	1.413 (3)
N1—C1	1.461 (2)	C4—C5	1.389 (3)
N3—C7	1.344 (3)	C9—C7	1.372 (3)
N3—C8	1.347 (3)	N4—C19	1.321 (3)
O3—C2	1.328 (2)	N4—C20	1.322 (3)
N2—C11	1.358 (2)	N5—C16	1.356 (2)
N2—C12	1.453 (3)	N5—C15	1.445 (3)
N2—C13	1.456 (2)	N5—C14	1.446 (3)
C6—C5	1.396 (3)	C16—C17	1.385 (3)
C6—C1	1.400 (2)	C16—C18	1.393 (3)
C10—C8	1.373 (3)	C17—C20	1.372 (3)
C10—C11	1.413 (3)	C19—C18	1.370 (3)
C3—C4	1.381 (3)
O2—N1—O1	122.91 (17)	O3—C2—C1	117.80 (17)
O2—N1—C1	118.27 (15)	C3—C2—C1	117.26 (16)
O1—N1—C1	118.82 (16)	C3—C4—C5	122.17 (18)
C7—N3—C8	116.00 (16)	N3—C8—C10	124.41 (19)
C11—N2—C12	120.43 (16)	C4—C5—C6	120.10 (17)
C11—N2—C13	120.95 (16)	C7—C9—C11	119.59 (19)
C12—N2—C13	118.62 (16)	N3—C7—C9	124.40 (18)
O4—C6—C5	124.13 (16)	C19—N4—C20	115.08 (19)
O4—C6—C1	118.81 (16)	C16—N5—C15	120.7 (2)
C5—C6—C1	117.02 (16)	C16—N5—C14	121.1 (2)
C8—C10—C11	119.49 (18)	C15—N5—C14	118.23 (19)
C4—C3—C2	119.81 (17)	N5—C16—C17	122.0 (2)
C6—C1—C2	123.64 (16)	N5—C16—C18	123.1 (2)
C6—C1—N1	118.64 (15)	C17—C16—C18	114.88 (19)
C2—C1—N1	117.69 (15)	C20—C17—C16	120.3 (2)
N2—C11—C10	121.79 (16)	N4—C20—C17	124.8 (2)
N2—C11—C9	122.17 (17)	N4—C19—C18	124.8 (2)
C10—C11—C9	116.03 (17)	C19—C18—C16	120.2 (2)
O3—C2—C3	124.91 (16)

(12NRES-4DMAP-II)

Crystal data

C13H15N3O4	F(000) = 584
Mr = 277.28	Dx = 1.404 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
a = 10.1301 (13) Å	Cell parameters from 11747 reflections
b = 12.6967 (17) Å	θ = 3.1–27.5°
c = 10.3338 (14) Å	µ = 0.11 mm^−1
β = 99.170 (7)°	T = 150 K
V = 1312.1 (3) Å^3	Block, brown
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2568 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.027
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −13→13
Tmin = 0.873, Tmax = 1.000	k = −16→16
13192 measured reflections	l = −13→13
3009 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 0.5219P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3009 reflections	Δρmax = 0.24 e Å^−3
189 parameters	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.83809 (9)	0.26442 (7)	0.32904 (8)	0.0225 (2)
O2	0.53573 (9)	0.15051 (7)	−0.04164 (9)	0.0222 (2)
O3	0.62117 (11)	0.04678 (7)	0.20127 (10)	0.0323 (2)
O4	0.56850 (12)	0.18141 (9)	0.30863 (11)	0.0442 (3)
N3	0.62215 (10)	0.14152 (8)	0.22227 (10)	0.0210 (2)
N1	0.70849 (11)	0.36971 (9)	0.50172 (10)	0.0224 (2)
N2	0.56869 (11)	0.54280 (8)	0.78994 (11)	0.0235 (2)
C9	0.79649 (11)	0.27240 (9)	0.20174 (11)	0.0173 (2)
C8	0.68854 (11)	0.21079 (9)	0.14036 (11)	0.0163 (2)
C13	0.63845 (12)	0.21410 (9)	0.00593 (12)	0.0174 (2)
C5	0.61419 (12)	0.48747 (9)	0.69533 (12)	0.0189 (3)
C10	0.85602 (12)	0.33926 (10)	0.11860 (12)	0.0206 (3)
H10	0.929336	0.380201	0.153158	0.025*
C12	0.69836 (13)	0.28344 (10)	−0.07127 (12)	0.0214 (3)
H12	0.666561	0.289003	−0.160528	0.026*
C11	0.80628 (13)	0.34450 (10)	−0.01405 (13)	0.0228 (3)
H11	0.846177	0.390213	−0.066575	0.027*
C3	0.53614 (13)	0.40670 (10)	0.62492 (12)	0.0217 (3)
H3	0.450970	0.392175	0.643022	0.026*
C2	0.58557 (13)	0.35063 (10)	0.53120 (12)	0.0228 (3)
H2	0.533418	0.297855	0.486336	0.027*
C4	0.74202 (12)	0.50577 (10)	0.66002 (12)	0.0212 (3)
H4	0.796760	0.558338	0.702058	0.025*
C1	0.78489 (13)	0.44663 (10)	0.56476 (12)	0.0223 (3)
H1	0.868885	0.459662	0.542725	0.027*
C6	0.43747 (14)	0.51932 (11)	0.82476 (14)	0.0281 (3)
H6A	0.420588	0.565777	0.893583	0.042*
H6B	0.369821	0.529097	0.749384	0.042*
H6C	0.435829	0.447689	0.854188	0.042*
C7	0.64904 (16)	0.62614 (11)	0.86083 (15)	0.0327 (3)
H7A	0.600875	0.656788	0.924288	0.049*
H7B	0.731709	0.597100	0.904677	0.049*
H7C	0.667413	0.679364	0.800154	0.049*
H2A	0.469 (2)	0.1849 (18)	−0.100 (2)	0.064 (6)*
H1A	0.7412 (18)	0.3302 (14)	0.4382 (17)	0.040 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0193 (4)	0.0294 (5)	0.0174 (4)	−0.0024 (4)	−0.0008 (3)	−0.0039 (4)
O2	0.0190 (4)	0.0215 (4)	0.0228 (4)	0.0000 (3)	−0.0064 (4)	−0.0004 (4)
O3	0.0436 (6)	0.0203 (5)	0.0324 (5)	−0.0034 (4)	0.0044 (5)	0.0047 (4)
O4	0.0512 (7)	0.0455 (7)	0.0443 (6)	−0.0131 (5)	0.0335 (6)	−0.0117 (5)
N3	0.0184 (5)	0.0255 (6)	0.0182 (5)	−0.0032 (4)	0.0002 (4)	−0.0004 (4)
N1	0.0266 (6)	0.0231 (5)	0.0182 (5)	0.0014 (4)	0.0060 (4)	−0.0003 (4)
N2	0.0248 (6)	0.0217 (5)	0.0256 (5)	0.0003 (4)	0.0087 (4)	−0.0020 (4)
C9	0.0146 (5)	0.0181 (5)	0.0189 (6)	0.0030 (4)	0.0016 (4)	−0.0038 (5)
C8	0.0148 (5)	0.0162 (5)	0.0180 (6)	0.0017 (4)	0.0028 (4)	−0.0008 (4)
C13	0.0151 (5)	0.0168 (6)	0.0196 (6)	0.0042 (4)	0.0002 (4)	−0.0029 (4)
C5	0.0214 (6)	0.0176 (6)	0.0177 (6)	0.0023 (5)	0.0035 (5)	0.0040 (4)
C10	0.0163 (6)	0.0180 (6)	0.0279 (6)	−0.0010 (4)	0.0049 (5)	−0.0038 (5)
C12	0.0263 (7)	0.0217 (6)	0.0158 (6)	0.0054 (5)	0.0018 (5)	0.0018 (5)
C11	0.0245 (6)	0.0194 (6)	0.0266 (7)	0.0017 (5)	0.0102 (5)	0.0024 (5)
C3	0.0197 (6)	0.0228 (6)	0.0228 (6)	−0.0024 (5)	0.0038 (5)	0.0039 (5)
C2	0.0263 (7)	0.0209 (6)	0.0205 (6)	−0.0039 (5)	0.0013 (5)	0.0008 (5)
C4	0.0208 (6)	0.0204 (6)	0.0221 (6)	−0.0032 (5)	0.0027 (5)	−0.0005 (5)
C1	0.0203 (6)	0.0244 (6)	0.0231 (6)	−0.0005 (5)	0.0056 (5)	0.0041 (5)
C6	0.0256 (7)	0.0316 (7)	0.0291 (7)	0.0051 (6)	0.0110 (6)	0.0007 (6)
C7	0.0378 (8)	0.0287 (7)	0.0334 (8)	−0.0035 (6)	0.0110 (6)	−0.0107 (6)

Geometric parameters (Å, º)

O1—C9	1.3197 (14)	C10—C11	1.3846 (18)
O2—C13	1.3467 (14)	C10—H10	0.9300
O2—H2A	0.94 (2)	C12—C11	1.3927 (18)
O3—N3	1.2220 (14)	C12—H12	0.9300
O4—N3	1.2259 (14)	C11—H11	0.9300
N3—C8	1.4573 (15)	C3—C2	1.3601 (18)
N1—C1	1.3478 (17)	C3—H3	0.9300
N1—C2	1.3502 (17)	C2—H2	0.9300
N1—H1A	0.928 (18)	C4—C1	1.3630 (18)
N2—C5	1.3437 (16)	C4—H4	0.9300
N2—C7	1.4591 (18)	C1—H1	0.9300
N2—C6	1.4622 (17)	C6—H6A	0.9600
C9—C10	1.4098 (17)	C6—H6B	0.9600
C9—C8	1.4102 (16)	C6—H6C	0.9600
C8—C13	1.4015 (16)	C7—H7A	0.9600
C13—C12	1.3907 (17)	C7—H7B	0.9600
C5—C4	1.4194 (17)	C7—H7C	0.9600
C5—C3	1.4222 (17)
C13—O2—H2A	113.1 (14)	C10—C11—C12	122.06 (12)
O3—N3—O4	122.95 (11)	C10—C11—H11	119.0
O3—N3—C8	118.84 (10)	C12—C11—H11	119.0
O4—N3—C8	118.21 (11)	C2—C3—C5	120.27 (12)
C1—N1—C2	120.01 (11)	C2—C3—H3	119.9
C1—N1—H1A	119.4 (11)	C5—C3—H3	119.9
C2—N1—H1A	120.6 (11)	N1—C2—C3	121.61 (12)
C5—N2—C7	121.06 (11)	N1—C2—H2	119.2
C5—N2—C6	120.21 (11)	C3—C2—H2	119.2
C7—N2—C6	118.72 (11)	C1—C4—C5	120.28 (12)
O1—C9—C10	123.64 (11)	C1—C4—H4	119.9
O1—C9—C8	120.49 (11)	C5—C4—H4	119.9
C10—C9—C8	115.86 (11)	N1—C1—C4	121.58 (12)
C13—C8—C9	124.16 (11)	N1—C1—H1	119.2
C13—C8—N3	117.78 (10)	C4—C1—H1	119.2
C9—C8—N3	118.04 (10)	N2—C6—H6A	109.5
O2—C13—C12	123.55 (11)	N2—C6—H6B	109.5
O2—C13—C8	118.72 (11)	H6A—C6—H6B	109.5
C12—C13—C8	117.74 (11)	N2—C6—H6C	109.5
N2—C5—C4	122.29 (11)	H6A—C6—H6C	109.5
N2—C5—C3	121.47 (11)	H6B—C6—H6C	109.5
C4—C5—C3	116.24 (11)	N2—C7—H7A	109.5
C11—C10—C9	120.58 (11)	N2—C7—H7B	109.5
C11—C10—H10	119.7	H7A—C7—H7B	109.5
C9—C10—H10	119.7	N2—C7—H7C	109.5
C13—C12—C11	119.58 (11)	H7A—C7—H7C	109.5
C13—C12—H12	120.2	H7B—C7—H7C	109.5
C11—C12—H12	120.2

(13NRES-TMP-PYR)

Crystal data

C29H26N3O4	F(000) = 506
Mr = 480.53	Dx = 1.322 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71075 Å
a = 7.7925 (13) Å	Cell parameters from 9438 reflections
b = 12.885 (2) Å	θ = 3.1–27.6°
c = 12.398 (2) Å	µ = 0.09 mm^−1
β = 104.054 (7)°	T = 150 K
V = 1207.6 (4) Å^3	Block, yellow
Z = 2	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3193 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.057
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −10→10
Tmin = 0.710, Tmax = 1.000	k = −16→16
12163 measured reflections	l = −16→16
5506 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.091	w = 1/[σ^2(Fo^2) + (0.1152P)^2 + 1.4802P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.276	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.47 e Å^−3
5506 reflections	Δρmin = −0.35 e Å^−3
340 parameters	Absolute structure: Flack x determined using 988 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: 1.5 (10)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	−0.8237 (8)	−0.4406 (4)	−0.3005 (5)	0.0487 (15)
O4	−0.5663 (6)	−0.5084 (6)	−0.4455 (3)	0.0445 (14)
H4	−0.508079	−0.528346	−0.488395	0.067*
N3	−0.4249 (7)	−0.5172 (6)	0.3740 (4)	0.0327 (12)
O3	−0.5609 (7)	−0.5250 (6)	−0.0685 (4)	0.0499 (14)
H3	−0.496933	−0.519335	−0.005639	0.075*
N1	−0.7422 (7)	−0.5218 (6)	−0.2834 (4)	0.0326 (13)
N2	−0.4071 (8)	−0.5266 (5)	0.1548 (4)	0.0329 (13)
C13	−0.4217 (11)	−0.6113 (5)	0.2110 (6)	0.0318 (17)
O2	−0.8155 (10)	−0.6067 (5)	−0.2897 (6)	0.064 (2)
C12	−0.4317 (10)	−0.6079 (5)	0.3214 (6)	0.0285 (16)
C2	−0.4640 (9)	−0.5088 (6)	−0.3406 (5)	0.0341 (16)
C1	−0.5497 (8)	−0.5152 (6)	−0.2554 (5)	0.0278 (13)
C6	−0.4624 (9)	−0.5178 (7)	−0.1434 (5)	0.0359 (15)
C9	−0.4048 (10)	−0.4289 (6)	0.3188 (6)	0.0312 (17)
C5	−0.2754 (11)	−0.5088 (8)	−0.1164 (6)	0.048 (2)
H5	−0.211816	−0.506923	−0.042496	0.058*
C3	−0.2789 (10)	−0.5020 (7)	−0.3122 (6)	0.0391 (18)
H3A	−0.216978	−0.496970	−0.367411	0.047*
C14	−0.4315 (13)	−0.7138 (6)	0.1487 (7)	0.046 (2)
H14A	−0.545543	−0.744797	0.142388	0.069*
H14B	−0.341256	−0.759807	0.188761	0.069*
H14C	−0.413716	−0.701588	0.075839	0.069*
C11	−0.4503 (15)	−0.7040 (6)	0.3851 (7)	0.052 (2)
H11A	−0.567753	−0.731219	0.359303	0.078*
H11B	−0.428986	−0.687631	0.462812	0.078*
H11C	−0.365968	−0.754795	0.374246	0.078*
C4	−0.1889 (10)	−0.5028 (7)	−0.2007 (6)	0.0436 (19)
H4A	−0.066054	−0.499259	−0.182414	0.052*
C8	−0.3979 (11)	−0.4331 (6)	0.2066 (6)	0.0365 (18)
C27	−0.9393 (15)	−0.4332 (10)	−0.5939 (9)	0.067 (3)
H27	−0.954460	−0.426095	−0.522159	0.080*
C30	−0.8851 (12)	−0.4578 (8)	−0.8089 (8)	0.052 (2)
C29	−0.9149 (11)	−0.5494 (7)	−0.7506 (8)	0.051 (2)
C10	−0.4009 (14)	−0.3274 (7)	0.3810 (9)	0.052 (2)
H10A	−0.500623	−0.285716	0.345106	0.078*
H10B	−0.293544	−0.290842	0.381042	0.078*
H10C	−0.406205	−0.341214	0.456203	0.078*
C21	−0.8578 (14)	−0.4716 (8)	−0.9155 (9)	0.065 (3)
C7	−0.3668 (18)	−0.3399 (7)	0.1442 (8)	0.067 (3)
H7A	−0.472134	−0.298308	0.126540	0.101*
H7B	−0.336834	−0.360826	0.076751	0.101*
H7C	−0.271394	−0.300228	0.188870	0.101*
C26	−0.9154 (14)	−0.3495 (9)	−0.6492 (9)	0.064 (3)
H26	−0.918443	−0.284034	−0.618109	0.076*
C28	−0.9430 (12)	−0.5378 (8)	−0.6422 (8)	0.060 (3)
C25	−0.8831 (15)	−0.3611 (9)	−0.7625 (10)	0.066 (3)
C22	−0.8393 (18)	−0.3783 (10)	−0.9768 (9)	0.082 (4)
H22	−0.823046	−0.383413	−1.048471	0.099*
C15	−0.9712 (15)	−0.6252 (9)	−0.5852 (11)	0.075 (3)
H15	−0.989690	−0.619593	−0.514083	0.090*
C24	−0.871 (2)	−0.2724 (10)	−0.8226 (13)	0.108 (6)
H24	−0.879980	−0.207257	−0.792229	0.129*
C23	−0.846 (3)	−0.2819 (10)	−0.9293 (12)	0.120 (6)
H23	−0.832580	−0.222481	−0.969268	0.144*
C0AA	−0.9213 (15)	−0.6473 (10)	−0.7960 (11)	0.070 (4)
C2AA	−0.9435 (19)	−0.7298 (11)	−0.7447 (14)	0.102 (6)
H2AA	−0.941615	−0.794417	−0.777825	0.123*
C1AA	−0.9717 (17)	−0.7216 (10)	−0.6345 (15)	0.095 (5)
H1AA	−0.990284	−0.781079	−0.596368	0.114*
C3AA	−0.861 (2)	−0.5829 (13)	−0.9426 (14)	0.046 (4)	0.5
H3AA	−0.848385	−0.599157	−1.013323	0.055*	0.5
C4AA	−0.879 (3)	−0.6604 (14)	−0.881 (3)	0.094 (11)	0.5
H4AA	−0.858439	−0.727330	−0.903681	0.112*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.039 (3)	0.041 (3)	0.065 (4)	0.014 (3)	0.011 (3)	0.008 (3)
O4	0.039 (3)	0.078 (4)	0.019 (2)	0.007 (3)	0.0121 (18)	0.001 (3)
N3	0.036 (3)	0.042 (3)	0.020 (2)	0.003 (3)	0.006 (2)	−0.001 (3)
O3	0.058 (3)	0.075 (4)	0.020 (2)	−0.017 (4)	0.015 (2)	−0.003 (3)
N1	0.042 (3)	0.038 (3)	0.023 (2)	−0.017 (3)	0.018 (2)	−0.011 (3)
N2	0.044 (3)	0.037 (3)	0.018 (2)	−0.006 (3)	0.007 (2)	−0.001 (3)
C13	0.042 (4)	0.027 (4)	0.026 (4)	−0.002 (3)	0.006 (3)	−0.006 (3)
O2	0.072 (5)	0.043 (4)	0.082 (5)	−0.018 (3)	0.031 (4)	−0.011 (3)
C12	0.028 (4)	0.032 (4)	0.025 (4)	−0.004 (3)	0.005 (3)	0.004 (3)
C2	0.042 (4)	0.041 (4)	0.017 (3)	0.002 (4)	0.004 (3)	−0.001 (3)
C1	0.035 (3)	0.025 (3)	0.023 (3)	−0.005 (3)	0.009 (2)	0.000 (3)
C6	0.050 (4)	0.039 (4)	0.019 (3)	−0.002 (4)	0.010 (3)	0.002 (4)
C9	0.039 (4)	0.031 (4)	0.024 (4)	−0.005 (3)	0.008 (3)	0.000 (3)
C5	0.056 (5)	0.061 (5)	0.025 (3)	0.008 (5)	0.006 (3)	0.000 (4)
C3	0.041 (4)	0.051 (5)	0.031 (3)	0.001 (4)	0.017 (3)	−0.005 (4)
C14	0.063 (6)	0.039 (5)	0.032 (4)	0.001 (4)	0.007 (4)	−0.015 (3)
C11	0.082 (7)	0.038 (5)	0.032 (5)	−0.001 (4)	0.008 (4)	0.010 (4)
C4	0.034 (4)	0.060 (6)	0.038 (4)	0.007 (4)	0.012 (3)	−0.001 (4)
C8	0.049 (5)	0.039 (4)	0.021 (4)	−0.010 (4)	0.008 (3)	−0.003 (3)
C27	0.063 (7)	0.091 (8)	0.046 (6)	0.006 (6)	0.013 (5)	0.013 (6)
C30	0.047 (5)	0.059 (6)	0.053 (5)	−0.008 (4)	0.015 (4)	−0.003 (5)
C29	0.037 (5)	0.049 (6)	0.062 (5)	−0.002 (4)	0.002 (4)	−0.002 (4)
C10	0.060 (6)	0.041 (5)	0.058 (6)	0.002 (4)	0.019 (5)	−0.015 (4)
C21	0.057 (6)	0.068 (7)	0.067 (7)	−0.002 (5)	0.010 (5)	0.004 (5)
C7	0.114 (10)	0.048 (6)	0.038 (5)	−0.024 (6)	0.016 (6)	−0.001 (4)
C26	0.051 (6)	0.077 (7)	0.065 (7)	0.005 (5)	0.016 (5)	0.004 (6)
C28	0.048 (5)	0.066 (7)	0.058 (5)	−0.001 (5)	−0.005 (4)	0.000 (5)
C25	0.058 (7)	0.066 (7)	0.067 (7)	0.005 (5)	0.005 (5)	0.027 (6)
C22	0.109 (10)	0.091 (9)	0.056 (7)	−0.050 (8)	0.040 (7)	−0.014 (6)
C15	0.047 (6)	0.072 (8)	0.089 (8)	−0.006 (5)	−0.017 (6)	0.020 (6)
C24	0.178 (17)	0.055 (7)	0.110 (11)	−0.025 (8)	0.075 (11)	−0.020 (7)
C23	0.22 (2)	0.068 (8)	0.094 (10)	−0.047 (11)	0.076 (12)	−0.007 (7)
C0AA	0.046 (6)	0.071 (9)	0.077 (8)	0.022 (6)	−0.014 (5)	−0.036 (6)
C2AA	0.087 (10)	0.053 (8)	0.132 (14)	0.003 (7)	−0.038 (9)	−0.018 (8)
C1AA	0.061 (8)	0.069 (8)	0.127 (13)	−0.015 (6)	−0.031 (8)	0.000 (8)
C3AA	0.050 (11)	0.037 (10)	0.041 (9)	0.025 (8)	−0.006 (8)	−0.009 (7)
C4AA	0.044 (12)	0.015 (9)	0.22 (4)	−0.002 (8)	0.038 (17)	−0.008 (14)

Geometric parameters (Å, º)

O1—N1	1.216 (8)	C27—H27	0.9300
O4—C2	1.350 (7)	C30—C25	1.371 (15)
O4—H4	0.8200	C30—C21	1.400 (14)
N3—C12	1.333 (10)	C30—C29	1.433 (12)
N3—C9	1.356 (10)	C29—C0AA	1.377 (14)
O3—C6	1.343 (8)	C29—C28	1.421 (13)
O3—H3	0.8200	C10—H10A	0.9600
N1—O2	1.227 (9)	C10—H10B	0.9600
N1—C1	1.458 (8)	C10—H10C	0.9600
N2—C13	1.313 (10)	C21—C22	1.447 (16)
N2—C8	1.359 (10)	C21—C3AA	1.473 (18)
C13—C12	1.391 (11)	C7—H7A	0.9600
C13—C14	1.523 (10)	C7—H7B	0.9600
C12—C11	1.495 (11)	C7—H7C	0.9600
C2—C1	1.382 (8)	C26—C25	1.493 (16)
C2—C3	1.402 (10)	C26—H26	0.9300
C1—C6	1.391 (8)	C28—C15	1.375 (15)
C6—C5	1.419 (11)	C25—C24	1.380 (17)
C9—C8	1.407 (10)	C22—C23	1.381 (18)
C9—C10	1.515 (11)	C22—H22	0.9300
C5—C4	1.376 (10)	C15—C1AA	1.383 (18)
C5—H5	0.9300	C15—H15	0.9300
C3—C4	1.390 (10)	C24—C23	1.390 (18)
C3—H3A	0.9300	C24—H24	0.9300
C14—H14A	0.9600	C23—H23	0.9300
C14—H14B	0.9600	C0AA—C4AA	1.20 (3)
C14—H14C	0.9600	C0AA—C2AA	1.27 (2)
C11—H11A	0.9600	C2AA—C1AA	1.44 (2)
C11—H11B	0.9600	C2AA—H2AA	0.9300
C11—H11C	0.9600	C1AA—H1AA	0.9300
C4—H4A	0.9300	C3AA—C4AA	1.28 (3)
C8—C7	1.479 (12)	C3AA—H3AA	0.9300
C27—C26	1.315 (15)	C4AA—H4AA	0.9300
C27—C28	1.472 (16)
C2—O4—H4	109.5	C0AA—C29—C28	119.0 (11)
C12—N3—C9	119.0 (5)	C0AA—C29—C30	122.9 (11)
C6—O3—H3	109.5	C28—C29—C30	118.2 (8)
O1—N1—O2	122.7 (6)	C9—C10—H10A	109.5
O1—N1—C1	117.1 (7)	C9—C10—H10B	109.5
O2—N1—C1	120.2 (7)	H10A—C10—H10B	109.5
C13—N2—C8	119.2 (5)	C9—C10—H10C	109.5
N2—C13—C12	121.9 (6)	H10A—C10—H10C	109.5
N2—C13—C14	116.9 (7)	H10B—C10—H10C	109.5
C12—C13—C14	121.2 (7)	C30—C21—C22	116.6 (10)
N3—C12—C13	120.3 (6)	C30—C21—C3AA	109.9 (11)
N3—C12—C11	117.7 (7)	C22—C21—C3AA	133.4 (13)
C13—C12—C11	122.0 (7)	C8—C7—H7A	109.5
O4—C2—C1	117.0 (6)	C8—C7—H7B	109.5
O4—C2—C3	124.9 (6)	H7A—C7—H7B	109.5
C1—C2—C3	118.1 (5)	C8—C7—H7C	109.5
C2—C1—C6	123.7 (6)	H7A—C7—H7C	109.5
C2—C1—N1	118.8 (5)	H7B—C7—H7C	109.5
C6—C1—N1	117.5 (5)	C27—C26—C25	119.1 (11)
O3—C6—C1	118.0 (6)	C27—C26—H26	120.5
O3—C6—C5	124.7 (5)	C25—C26—H26	120.5
C1—C6—C5	117.3 (6)	C15—C28—C29	118.7 (10)
N3—C9—C8	120.3 (6)	C15—C28—C27	122.1 (10)
N3—C9—C10	117.3 (7)	C29—C28—C27	119.2 (9)
C8—C9—C10	122.4 (7)	C30—C25—C24	121.4 (11)
C4—C5—C6	119.3 (6)	C30—C25—C26	119.9 (9)
C4—C5—H5	120.3	C24—C25—C26	118.4 (11)
C6—C5—H5	120.3	C23—C22—C21	120.3 (11)
C4—C3—C2	119.2 (6)	C23—C22—H22	119.8
C4—C3—H3A	120.4	C21—C22—H22	119.8
C2—C3—H3A	120.4	C28—C15—C1AA	119.5 (14)
C13—C14—H14A	109.5	C28—C15—H15	120.3
C13—C14—H14B	109.5	C1AA—C15—H15	120.3
H14A—C14—H14B	109.5	C25—C24—C23	119.1 (12)
C13—C14—H14C	109.5	C25—C24—H24	120.4
H14A—C14—H14C	109.5	C23—C24—H24	120.4
H14B—C14—H14C	109.5	C22—C23—C24	120.8 (11)
C12—C11—H11A	109.5	C22—C23—H23	119.6
C12—C11—H11B	109.5	C24—C23—H23	119.6
H11A—C11—H11B	109.5	C4AA—C0AA—C2AA	115.2 (15)
C12—C11—H11C	109.5	C4AA—C0AA—C29	120.1 (17)
H11A—C11—H11C	109.5	C2AA—C0AA—C29	123.8 (15)
H11B—C11—H11C	109.5	C0AA—C2AA—C1AA	118.9 (14)
C5—C4—C3	122.3 (7)	C0AA—C2AA—H2AA	120.5
C5—C4—H4A	118.9	C1AA—C2AA—H2AA	120.5
C3—C4—H4A	118.9	C15—C1AA—C2AA	120.0 (13)
N2—C8—C9	119.4 (6)	C15—C1AA—H1AA	120.0
N2—C8—C7	118.0 (7)	C2AA—C1AA—H1AA	120.0
C9—C8—C7	122.5 (7)	C4AA—C3AA—C21	129 (2)
C26—C27—C28	122.0 (10)	C4AA—C3AA—H3AA	115.7
C26—C27—H27	119.0	C21—C3AA—H3AA	115.7
C28—C27—H27	119.0	C0AA—C4AA—C3AA	120 (2)
C25—C30—C21	121.5 (9)	C0AA—C4AA—H4AA	119.8
C25—C30—C29	121.6 (9)	C3AA—C4AA—H4AA	119.8
C21—C30—C29	116.9 (9)

(14NRES-4DMAP-PYR)

Crystal data

C58H50N6O8	Z = 2
Mr = 959.04	F(000) = 1008
Triclinic, P1	Dx = 1.304 Mg m^−3
a = 13.337 (3) Å	Mo Kα radiation, λ = 0.71075 Å
b = 13.504 (3) Å	Cell parameters from 14998 reflections
c = 16.069 (3) Å	θ = 3.1–28.2°
α = 75.831 (5)°	µ = 0.09 mm^−1
β = 66.422 (5)°	T = 150 K
γ = 67.934 (5)°	Block, colorless
V = 2442.9 (8) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	4435 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.062
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −17→17
Tmin = 0.804, Tmax = 1.000	k = −17→17
25588 measured reflections	l = −20→20
11144 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.087	H-atom parameters constrained
wR(F^2) = 0.284	w = 1/[σ^2(Fo^2) + (0.1128P)^2 + 0.737P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
11144 reflections	Δρmax = 0.36 e Å^−3
655 parameters	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O60	0.7180 (2)	0.06012 (17)	0.31313 (16)	0.0517 (6)
O61	0.6864 (2)	0.43167 (18)	0.27054 (18)	0.0576 (7)
O63	0.5142 (2)	0.3393 (2)	0.37148 (19)	0.0691 (8)
N71	0.6024 (3)	0.2651 (2)	0.3728 (2)	0.0485 (7)
O64	0.7690 (3)	0.5800 (2)	0.18932 (18)	0.0692 (8)
H64	0.745616	0.529237	0.218528	0.104*
O62	0.6068 (3)	0.2053 (2)	0.44286 (19)	0.0870 (10)
O67	0.7839 (3)	0.9091 (2)	0.2175 (2)	0.0860 (10)
H67	0.750107	0.958279	0.249942	0.129*
N72	0.7881 (3)	−0.0097 (2)	0.4547 (2)	0.0572 (8)
H72	0.747051	0.017688	0.419879	0.069*
N69	0.3246 (3)	0.6258 (2)	0.0293 (2)	0.0590 (8)
C1	0.7020 (3)	0.2466 (3)	0.2910 (2)	0.0414 (8)
N68	0.5099 (3)	0.5050 (3)	0.2037 (2)	0.0628 (9)
H68	0.548226	0.479902	0.240563	0.075*
C2	0.7411 (3)	0.3356 (3)	0.2427 (2)	0.0416 (8)
C6	0.7565 (3)	0.1418 (3)	0.2641 (2)	0.0423 (8)
N70	0.8315 (5)	0.7604 (4)	0.1113 (3)	0.0870 (13)
N73	0.9842 (3)	−0.1401 (3)	0.6204 (3)	0.0693 (10)
C3	0.8410 (3)	0.3140 (3)	0.1655 (3)	0.0512 (9)
H3	0.871893	0.368958	0.132502	0.061*
C8	0.7452 (3)	0.6500 (3)	0.2463 (2)	0.0475 (9)
C7	0.7733 (3)	0.7439 (3)	0.2103 (2)	0.0508 (9)
C5	0.8521 (3)	0.1282 (3)	0.1847 (3)	0.0546 (10)
H5	0.888238	0.061300	0.162856	0.066*
C4	0.8941 (3)	0.2123 (3)	0.1379 (3)	0.0543 (10)
H4	0.960115	0.200223	0.086287	0.065*
C12	0.7494 (3)	0.8239 (3)	0.2615 (3)	0.0551 (10)
C17	0.3856 (3)	0.5860 (3)	0.0856 (3)	0.0507 (9)
C15	0.4754 (3)	0.6232 (3)	0.0764 (3)	0.0594 (10)
H15	0.494401	0.676440	0.029670	0.071*
C21	0.7470 (4)	0.0177 (3)	0.5394 (3)	0.0621 (11)
H21	0.673797	0.066837	0.560057	0.075*
C20	0.8927 (4)	−0.0797 (3)	0.4246 (3)	0.0630 (11)
H20	0.920355	−0.098197	0.365536	0.076*
C24	0.9206 (4)	−0.0980 (3)	0.5664 (3)	0.0547 (10)
C13	0.5343 (3)	0.5816 (3)	0.1356 (3)	0.0613 (10)
H13	0.593350	0.607125	0.128526	0.074*
C22	0.8088 (4)	−0.0239 (3)	0.5955 (3)	0.0608 (11)
H22	0.777607	−0.003588	0.654241	0.073*
C9	0.6920 (4)	0.6361 (3)	0.3395 (3)	0.0648 (11)
H9	0.672746	0.573495	0.367077	0.078*
C11	0.6958 (4)	0.8070 (3)	0.3537 (3)	0.0674 (12)
H11	0.678497	0.858666	0.390667	0.081*
C23	0.9609 (4)	−0.1253 (3)	0.4770 (3)	0.0640 (11)
H23	1.033636	−0.174073	0.453878	0.077*
C10	0.6672 (4)	0.7144 (4)	0.3921 (3)	0.0735 (13)
H10	0.630380	0.704355	0.454930	0.088*
C16	0.3628 (4)	0.5045 (3)	0.1589 (3)	0.0636 (11)
H16	0.304560	0.476546	0.168535	0.076*
C14	0.4255 (4)	0.4680 (3)	0.2138 (3)	0.0680 (12)
H14	0.409505	0.414506	0.261248	0.082*
C19	0.3476 (4)	0.7086 (3)	−0.0449 (3)	0.0700 (12)
H19A	0.325939	0.774876	−0.020736	0.105*
H19B	0.304007	0.717983	−0.083034	0.105*
H19C	0.428292	0.688048	−0.080374	0.105*
C58	0.2295 (4)	0.8100 (4)	0.2191 (4)	0.0800 (14)
C57	0.2657 (4)	0.7396 (4)	0.2898 (4)	0.0797 (14)
C41	0.3115 (5)	0.2338 (4)	0.2316 (4)	0.0864 (16)
C18	0.2284 (4)	0.5884 (4)	0.0428 (3)	0.0812 (14)
H18A	0.257227	0.513869	0.033298	0.122*
H18B	0.190273	0.629844	0.000003	0.122*
H18C	0.174711	0.597070	0.103926	0.122*
O65	0.9323 (5)	0.7146 (6)	0.0804 (3)	0.177 (3)
C42	0.2039 (5)	0.3076 (4)	0.2650 (5)	0.0901 (16)
C48	0.1379 (5)	0.8067 (5)	0.1978 (5)	0.0988 (17)
C26	1.0995 (4)	−0.2161 (4)	0.5898 (4)	0.0931 (16)
H26A	1.095101	−0.281137	0.579345	0.140*
H26B	1.133810	−0.232006	0.635830	0.140*
H26C	1.145565	−0.185329	0.534129	0.140*
O66	0.7767 (7)	0.8176 (4)	0.0666 (3)	0.186 (3)
C27	0.3381 (8)	0.2142 (6)	0.3795 (6)	0.116 (2)
H27	0.381314	0.183492	0.417914	0.139*
C59	0.2068 (5)	0.6636 (4)	0.3404 (4)	0.0969 (17)
C54	0.3576 (5)	0.7435 (5)	0.3108 (5)	0.0994 (18)
C25	0.9397 (5)	−0.1098 (4)	0.7124 (3)	0.0919 (16)
H25A	0.926462	−0.034228	0.709301	0.138*
H25B	0.994772	−0.149594	0.742527	0.138*
H25C	0.868682	−0.125573	0.746153	0.138*
C44	0.2888 (6)	0.8845 (5)	0.1660 (5)	0.111 (2)
C29	0.1611 (7)	0.3349 (6)	0.3576 (5)	0.1032 (18)
C36	0.3550 (8)	0.2048 (6)	0.1416 (6)	0.111 (2)
C33	0.1297 (7)	0.3602 (6)	0.2144 (6)	0.116 (2)
C34	0.1763 (9)	0.3278 (7)	0.1198 (7)	0.139 (3)
H34	0.131511	0.357688	0.082550	0.167*
C49	0.0815 (5)	0.7310 (6)	0.2510 (6)	0.115 (2)
H49	0.019605	0.728290	0.239438	0.138*
C50	0.1144 (6)	0.6634 (6)	0.3172 (6)	0.115 (2)
H50	0.075628	0.613651	0.349817	0.137*
C40	0.3839 (6)	0.1849 (5)	0.2867 (6)	0.111 (2)
C56	0.3830 (7)	0.8853 (6)	0.1897 (6)	0.130 (3)
H56	0.421563	0.935303	0.157788	0.156*
C28	0.2331 (9)	0.2859 (7)	0.4086 (6)	0.132 (3)
H28	0.206524	0.304084	0.467646	0.158*
C35	0.2821 (10)	0.2560 (8)	0.0876 (6)	0.139 (3)
H35	0.308574	0.239333	0.028116	0.166*
C37	0.4607 (9)	0.1330 (7)	0.1064 (6)	0.141 (3)
H37	0.487662	0.115168	0.047207	0.169*
C39	0.4856 (8)	0.1156 (7)	0.2551 (8)	0.139 (3)
H39	0.530935	0.084703	0.291873	0.167*
C53	0.3889 (7)	0.6712 (8)	0.3827 (6)	0.126 (2)
H53	0.447876	0.672647	0.398838	0.152*
C45	0.2531 (9)	0.9546 (6)	0.0967 (6)	0.151 (3)
H45	0.291196	1.004331	0.062040	0.181*
C55	0.4151 (6)	0.8162 (7)	0.2560 (7)	0.139 (3)
H55	0.478832	0.816566	0.266185	0.167*
C51	0.2425 (8)	0.5935 (6)	0.4097 (5)	0.137 (3)
H51	0.205736	0.542571	0.443446	0.164*
C32	0.0256 (8)	0.4308 (7)	0.2436 (10)	0.161 (4)
H32	−0.020091	0.462837	0.207177	0.193*
C46	0.1627 (10)	0.9510 (7)	0.0792 (7)	0.152 (4)
H46	0.139386	1.000050	0.033477	0.183*
C38	0.5283 (9)	0.0864 (7)	0.1644 (9)	0.158 (4)
H38	0.600893	0.036603	0.143037	0.190*
C47	0.1048 (7)	0.8780 (7)	0.1262 (6)	0.129 (3)
H47	0.045293	0.875520	0.111309	0.155*
C52	0.3300 (9)	0.5991 (8)	0.4279 (6)	0.151 (3)
H52	0.351926	0.550592	0.474445	0.181*
C30	0.0562 (8)	0.4056 (6)	0.3904 (7)	0.136 (3)
H30	0.028151	0.422522	0.449934	0.163*
C31	−0.0104 (10)	0.4536 (8)	0.3343 (10)	0.173 (5)
H31	−0.082376	0.503340	0.357872	0.208*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O60	0.0781 (18)	0.0322 (13)	0.0549 (15)	−0.0257 (12)	−0.0287 (14)	0.0015 (11)
O61	0.0679 (17)	0.0312 (14)	0.0784 (18)	−0.0189 (12)	−0.0267 (15)	−0.0059 (12)
O63	0.0545 (17)	0.0562 (18)	0.0702 (19)	−0.0035 (14)	−0.0138 (15)	0.0026 (14)
N71	0.055 (2)	0.0371 (17)	0.0495 (19)	−0.0144 (15)	−0.0152 (16)	−0.0027 (14)
O64	0.102 (2)	0.0521 (17)	0.0652 (17)	−0.0451 (16)	−0.0168 (17)	−0.0135 (13)
O62	0.082 (2)	0.077 (2)	0.0531 (18)	0.0034 (16)	−0.0129 (17)	0.0130 (15)
O67	0.143 (3)	0.0513 (18)	0.0713 (19)	−0.057 (2)	−0.018 (2)	−0.0092 (14)
N72	0.078 (2)	0.0455 (19)	0.060 (2)	−0.0232 (17)	−0.038 (2)	0.0065 (15)
N69	0.065 (2)	0.054 (2)	0.062 (2)	−0.0207 (16)	−0.0275 (19)	0.0001 (16)
C1	0.049 (2)	0.0350 (19)	0.046 (2)	−0.0166 (15)	−0.0199 (18)	−0.0022 (15)
N68	0.071 (2)	0.047 (2)	0.068 (2)	−0.0036 (17)	−0.033 (2)	−0.0094 (17)
C2	0.054 (2)	0.0326 (19)	0.051 (2)	−0.0200 (16)	−0.0279 (19)	0.0011 (15)
C6	0.054 (2)	0.0329 (19)	0.050 (2)	−0.0130 (16)	−0.0279 (19)	−0.0043 (15)
N70	0.140 (4)	0.075 (3)	0.056 (3)	−0.064 (3)	−0.017 (3)	−0.004 (2)
N73	0.088 (3)	0.061 (2)	0.085 (3)	−0.030 (2)	−0.056 (2)	0.0051 (19)
C3	0.054 (2)	0.051 (2)	0.054 (2)	−0.0255 (18)	−0.022 (2)	0.0054 (18)
C8	0.057 (2)	0.038 (2)	0.054 (2)	−0.0226 (17)	−0.017 (2)	−0.0065 (16)
C7	0.072 (3)	0.043 (2)	0.046 (2)	−0.0320 (19)	−0.016 (2)	−0.0037 (16)
C5	0.067 (3)	0.041 (2)	0.056 (2)	−0.0075 (18)	−0.023 (2)	−0.0144 (17)
C4	0.051 (2)	0.061 (3)	0.048 (2)	−0.0205 (19)	−0.0135 (19)	−0.0015 (19)
C12	0.075 (3)	0.041 (2)	0.056 (2)	−0.0298 (19)	−0.018 (2)	−0.0078 (17)
C17	0.053 (2)	0.037 (2)	0.055 (2)	−0.0085 (17)	−0.014 (2)	−0.0094 (16)
C15	0.060 (3)	0.051 (2)	0.062 (3)	−0.0184 (19)	−0.016 (2)	−0.0058 (19)
C21	0.073 (3)	0.046 (2)	0.066 (3)	−0.013 (2)	−0.026 (2)	−0.0063 (19)
C20	0.088 (3)	0.050 (2)	0.057 (2)	−0.028 (2)	−0.027 (3)	−0.0020 (19)
C24	0.071 (3)	0.041 (2)	0.066 (3)	−0.0252 (19)	−0.035 (2)	0.0027 (18)
C13	0.055 (2)	0.054 (3)	0.072 (3)	−0.0134 (19)	−0.019 (2)	−0.013 (2)
C22	0.081 (3)	0.052 (2)	0.056 (2)	−0.023 (2)	−0.031 (2)	−0.0017 (19)
C9	0.084 (3)	0.059 (3)	0.058 (3)	−0.045 (2)	−0.012 (2)	0.000 (2)
C11	0.084 (3)	0.060 (3)	0.061 (3)	−0.029 (2)	−0.011 (2)	−0.025 (2)
C23	0.067 (3)	0.054 (3)	0.070 (3)	−0.018 (2)	−0.023 (2)	−0.007 (2)
C10	0.100 (4)	0.075 (3)	0.049 (2)	−0.051 (3)	−0.002 (2)	−0.013 (2)
C16	0.075 (3)	0.049 (2)	0.072 (3)	−0.023 (2)	−0.034 (3)	0.006 (2)
C14	0.076 (3)	0.051 (3)	0.073 (3)	−0.020 (2)	−0.029 (3)	0.005 (2)
C19	0.083 (3)	0.057 (3)	0.067 (3)	−0.020 (2)	−0.030 (3)	0.003 (2)
C58	0.061 (3)	0.054 (3)	0.102 (4)	−0.013 (2)	0.008 (3)	−0.040 (3)
C57	0.071 (3)	0.063 (3)	0.093 (4)	−0.016 (3)	−0.005 (3)	−0.038 (3)
C41	0.097 (4)	0.081 (4)	0.107 (5)	−0.064 (3)	−0.045 (4)	0.021 (3)
C18	0.077 (3)	0.089 (3)	0.089 (3)	−0.035 (3)	−0.038 (3)	0.002 (3)
O65	0.153 (5)	0.243 (7)	0.090 (3)	−0.095 (5)	0.038 (3)	−0.027 (4)
C42	0.094 (4)	0.077 (4)	0.126 (5)	−0.056 (3)	−0.049 (4)	0.010 (3)
C48	0.077 (4)	0.077 (4)	0.114 (5)	0.000 (3)	−0.006 (4)	−0.048 (4)
C26	0.090 (4)	0.074 (3)	0.137 (5)	−0.026 (3)	−0.071 (4)	0.006 (3)
O66	0.359 (9)	0.130 (4)	0.091 (3)	−0.074 (5)	−0.123 (5)	0.024 (3)
C27	0.174 (8)	0.119 (6)	0.116 (6)	−0.100 (5)	−0.090 (6)	0.038 (4)
C59	0.095 (4)	0.069 (4)	0.095 (4)	−0.021 (3)	0.005 (4)	−0.028 (3)
C54	0.081 (4)	0.088 (4)	0.113 (5)	−0.016 (3)	−0.002 (4)	−0.055 (4)
C25	0.138 (5)	0.086 (4)	0.089 (4)	−0.048 (3)	−0.076 (4)	0.010 (3)
C44	0.120 (5)	0.054 (3)	0.119 (5)	−0.022 (3)	0.006 (4)	−0.028 (3)
C29	0.115 (5)	0.092 (5)	0.123 (6)	−0.073 (4)	−0.032 (5)	0.003 (4)
C36	0.132 (6)	0.095 (5)	0.125 (6)	−0.082 (5)	−0.028 (5)	0.004 (4)
C33	0.119 (6)	0.099 (5)	0.170 (7)	−0.078 (4)	−0.087 (6)	0.051 (5)
C34	0.185 (9)	0.135 (7)	0.172 (9)	−0.113 (7)	−0.117 (8)	0.051 (6)
C49	0.082 (4)	0.113 (6)	0.146 (6)	−0.025 (4)	−0.011 (5)	−0.063 (5)
C50	0.091 (5)	0.103 (5)	0.136 (6)	−0.052 (4)	0.013 (4)	−0.044 (4)
C40	0.095 (5)	0.090 (4)	0.177 (8)	−0.061 (4)	−0.073 (5)	0.034 (4)
C56	0.108 (6)	0.085 (5)	0.174 (8)	−0.058 (5)	0.020 (5)	−0.051 (5)
C28	0.176 (8)	0.120 (6)	0.151 (7)	−0.106 (6)	−0.077 (7)	0.029 (5)
C35	0.208 (9)	0.152 (8)	0.130 (6)	−0.137 (7)	−0.094 (8)	0.050 (6)
C37	0.133 (7)	0.115 (6)	0.165 (8)	−0.086 (6)	0.005 (6)	−0.017 (6)
C39	0.102 (6)	0.111 (6)	0.221 (10)	−0.061 (5)	−0.079 (7)	0.040 (6)
C53	0.103 (5)	0.142 (7)	0.119 (6)	−0.001 (5)	−0.028 (5)	−0.064 (5)
C45	0.155 (8)	0.064 (5)	0.153 (8)	−0.015 (5)	0.011 (6)	−0.014 (5)
C55	0.092 (5)	0.116 (6)	0.205 (10)	−0.038 (5)	0.001 (6)	−0.089 (6)
C51	0.149 (7)	0.110 (6)	0.109 (6)	−0.031 (5)	−0.010 (5)	−0.014 (4)
C32	0.099 (6)	0.094 (6)	0.309 (15)	−0.046 (5)	−0.095 (8)	0.014 (7)
C46	0.151 (8)	0.082 (6)	0.158 (8)	0.030 (6)	−0.033 (7)	−0.040 (5)
C38	0.127 (7)	0.113 (6)	0.217 (11)	−0.071 (6)	−0.028 (8)	0.013 (7)
C47	0.117 (6)	0.103 (6)	0.133 (6)	0.023 (5)	−0.043 (5)	−0.046 (5)
C52	0.142 (8)	0.156 (9)	0.111 (6)	−0.009 (6)	−0.027 (6)	−0.031 (6)
C30	0.112 (6)	0.103 (6)	0.190 (9)	−0.057 (5)	−0.017 (6)	−0.030 (6)
C31	0.140 (9)	0.114 (7)	0.272 (15)	−0.056 (6)	−0.057 (10)	−0.028 (9)

Geometric parameters (Å, º)

O60—C6	1.333 (4)	C57—C54	1.417 (8)
O61—C2	1.314 (4)	C57—C59	1.421 (7)
O63—N71	1.230 (4)	C41—C42	1.383 (8)
N71—O62	1.222 (4)	C41—C36	1.420 (8)
N71—C1	1.439 (4)	C41—C40	1.439 (7)
O64—C8	1.343 (4)	C18—H18A	0.9600
O64—H64	0.8200	C18—H18B	0.9600
O67—C12	1.332 (4)	C18—H18C	0.9600
O67—H67	0.8200	C42—C33	1.406 (8)
N72—C20	1.329 (5)	C42—C29	1.451 (8)
N72—C21	1.338 (5)	C48—C49	1.407 (9)
N72—H72	0.8600	C48—C47	1.410 (9)
N69—C17	1.339 (5)	C26—H26A	0.9600
N69—C19	1.442 (5)	C26—H26B	0.9600
N69—C18	1.470 (5)	C26—H26C	0.9600
C1—C6	1.412 (4)	C27—C28	1.340 (10)
C1—C2	1.418 (4)	C27—C40	1.460 (10)
N68—C14	1.334 (5)	C27—H27	0.9300
N68—C13	1.337 (5)	C59—C51	1.390 (9)
N68—H68	0.8600	C59—C50	1.424 (9)
C2—C3	1.400 (5)	C54—C55	1.389 (10)
C6—C5	1.386 (5)	C54—C53	1.410 (9)
N70—O66	1.170 (6)	C25—H25A	0.9600
N70—O65	1.195 (6)	C25—H25B	0.9600
N70—C7	1.467 (5)	C25—H25C	0.9600
N73—C24	1.336 (5)	C44—C45	1.390 (10)
N73—C26	1.454 (6)	C44—C56	1.455 (10)
N73—C25	1.456 (6)	C29—C30	1.342 (9)
C3—C4	1.379 (5)	C29—C28	1.385 (9)
C3—H3	0.9300	C36—C37	1.361 (9)
C8—C9	1.376 (5)	C36—C35	1.432 (9)
C8—C7	1.380 (5)	C33—C32	1.326 (10)
C7—C12	1.383 (5)	C33—C34	1.501 (11)
C5—C4	1.376 (5)	C34—C35	1.354 (11)
C5—H5	0.9300	C34—H34	0.9300
C4—H4	0.9300	C49—C50	1.325 (8)
C12—C11	1.367 (5)	C49—H49	0.9300
C17—C15	1.408 (5)	C50—H50	0.9300
C17—C16	1.421 (5)	C40—C39	1.305 (10)
C15—C13	1.357 (5)	C56—C55	1.329 (10)
C15—H15	0.9300	C56—H56	0.9300
C21—C22	1.344 (5)	C28—H28	0.9300
C21—H21	0.9300	C35—H35	0.9300
C20—C23	1.362 (5)	C37—C38	1.427 (11)
C20—H20	0.9300	C37—H37	0.9300
C24—C23	1.407 (5)	C39—C38	1.433 (11)
C24—C22	1.412 (5)	C39—H39	0.9300
C13—H13	0.9300	C53—C52	1.366 (11)
C22—H22	0.9300	C53—H53	0.9300
C9—C10	1.376 (5)	C45—C46	1.363 (11)
C9—H9	0.9300	C45—H45	0.9300
C11—C10	1.372 (6)	C55—H55	0.9300
C11—H11	0.9300	C51—C52	1.343 (10)
C23—H23	0.9300	C51—H51	0.9300
C10—H10	0.9300	C32—C31	1.415 (13)
C16—C14	1.338 (5)	C32—H32	0.9300
C16—H16	0.9300	C46—C47	1.372 (11)
C14—H14	0.9300	C46—H46	0.9300
C19—H19A	0.9600	C38—H38	0.9300
C19—H19B	0.9600	C47—H47	0.9300
C19—H19C	0.9600	C52—H52	0.9300
C58—C57	1.411 (7)	C30—C31	1.393 (12)
C58—C48	1.413 (7)	C30—H30	0.9300
C58—C44	1.416 (8)	C31—H31	0.9300
O62—N71—O63	121.0 (3)	H18A—C18—H18B	109.5
O62—N71—C1	118.9 (3)	N69—C18—H18C	109.5
O63—N71—C1	120.1 (3)	H18A—C18—H18C	109.5
C8—O64—H64	109.5	H18B—C18—H18C	109.5
C12—O67—H67	109.5	C41—C42—C33	124.0 (7)
C20—N72—C21	119.5 (3)	C41—C42—C29	120.1 (6)
C20—N72—H72	120.2	C33—C42—C29	115.9 (7)
C21—N72—H72	120.2	C49—C48—C47	122.1 (8)
C17—N69—C19	122.0 (3)	C49—C48—C58	117.4 (6)
C17—N69—C18	120.7 (3)	C47—C48—C58	120.5 (7)
C19—N69—C18	117.2 (3)	N73—C26—H26A	109.5
C6—C1—C2	123.7 (3)	N73—C26—H26B	109.5
C6—C1—N71	118.9 (3)	H26A—C26—H26B	109.5
C2—C1—N71	117.4 (3)	N73—C26—H26C	109.5
C14—N68—C13	119.2 (4)	H26A—C26—H26C	109.5
C14—N68—H68	120.4	H26B—C26—H26C	109.5
C13—N68—H68	120.4	C28—C27—C40	119.2 (7)
O61—C2—C3	123.0 (3)	C28—C27—H27	120.4
O61—C2—C1	121.1 (3)	C40—C27—H27	120.4
C3—C2—C1	115.9 (3)	C51—C59—C57	118.3 (7)
O60—C6—C5	121.9 (3)	C51—C59—C50	123.6 (7)
O60—C6—C1	121.4 (3)	C57—C59—C50	118.1 (6)
C5—C6—C1	116.7 (3)	C55—C54—C53	123.7 (8)
O66—N70—O65	123.5 (6)	C55—C54—C57	117.3 (7)
O66—N70—C7	118.3 (6)	C53—C54—C57	118.9 (7)
O65—N70—C7	118.2 (5)	N73—C25—H25A	109.5
C24—N73—C26	121.8 (4)	N73—C25—H25B	109.5
C24—N73—C25	120.4 (4)	H25A—C25—H25B	109.5
C26—N73—C25	117.8 (4)	N73—C25—H25C	109.5
C4—C3—C2	120.9 (3)	H25A—C25—H25C	109.5
C4—C3—H3	119.6	H25B—C25—H25C	109.5
C2—C3—H3	119.6	C45—C44—C58	119.4 (8)
O64—C8—C9	124.4 (3)	C45—C44—C56	123.4 (8)
O64—C8—C7	118.8 (3)	C58—C44—C56	117.1 (7)
C9—C8—C7	116.8 (3)	C30—C29—C28	122.7 (9)
C8—C7—C12	124.2 (3)	C30—C29—C42	120.1 (8)
C8—C7—N70	118.1 (3)	C28—C29—C42	117.2 (7)
C12—C7—N70	117.7 (3)	C37—C36—C41	122.8 (8)
C4—C5—C6	120.9 (3)	C37—C36—C35	120.5 (10)
C4—C5—H5	119.5	C41—C36—C35	116.7 (8)
C6—C5—H5	119.5	C32—C33—C42	126.2 (10)
C5—C4—C3	121.8 (4)	C32—C33—C34	119.7 (9)
C5—C4—H4	119.1	C42—C33—C34	114.1 (8)
C3—C4—H4	119.1	C35—C34—C33	121.4 (8)
O67—C12—C11	125.4 (3)	C35—C34—H34	119.3
O67—C12—C7	117.5 (3)	C33—C34—H34	119.3
C11—C12—C7	117.0 (3)	C50—C49—C48	121.5 (7)
N69—C17—C15	122.0 (4)	C50—C49—H49	119.2
N69—C17—C16	122.0 (4)	C48—C49—H49	119.2
C15—C17—C16	116.0 (4)	C49—C50—C59	122.7 (7)
C13—C15—C17	120.1 (4)	C49—C50—H50	118.6
C13—C15—H15	119.9	C59—C50—H50	118.6
C17—C15—H15	119.9	C39—C40—C41	120.9 (9)
N72—C21—C22	121.7 (4)	C39—C40—C27	121.6 (9)
N72—C21—H21	119.2	C41—C40—C27	117.5 (7)
C22—C21—H21	119.2	C55—C56—C44	121.5 (7)
N72—C20—C23	122.4 (4)	C55—C56—H56	119.2
N72—C20—H20	118.8	C44—C56—H56	119.2
C23—C20—H20	118.8	C27—C28—C29	125.0 (8)
N73—C24—C23	121.9 (4)	C27—C28—H28	117.5
N73—C24—C22	122.1 (4)	C29—C28—H28	117.5
C23—C24—C22	116.0 (4)	C34—C35—C36	122.5 (9)
N68—C13—C15	121.9 (4)	C34—C35—H35	118.7
N68—C13—H13	119.0	C36—C35—H35	118.7
C15—C13—H13	119.0	C36—C37—C38	117.0 (9)
C21—C22—C24	120.7 (4)	C36—C37—H37	121.5
C21—C22—H22	119.6	C38—C37—H37	121.5
C24—C22—H22	119.6	C40—C39—C38	120.8 (9)
C10—C9—C8	120.2 (4)	C40—C39—H39	119.6
C10—C9—H9	119.9	C38—C39—H39	119.6
C8—C9—H9	119.9	C52—C53—C54	118.1 (8)
C12—C11—C10	120.5 (4)	C52—C53—H53	120.9
C12—C11—H11	119.8	C54—C53—H53	120.9
C10—C11—H11	119.8	C46—C45—C44	120.4 (9)
C20—C23—C24	119.6 (4)	C46—C45—H45	119.8
C20—C23—H23	120.2	C44—C45—H45	119.8
C24—C23—H23	120.2	C56—C55—C54	122.9 (8)
C11—C10—C9	121.3 (4)	C56—C55—H55	118.5
C11—C10—H10	119.3	C54—C55—H55	118.5
C9—C10—H10	119.3	C52—C51—C59	120.1 (9)
C14—C16—C17	119.7 (4)	C52—C51—H51	119.9
C14—C16—H16	120.1	C59—C51—H51	119.9
C17—C16—H16	120.1	C33—C32—C31	114.8 (11)
N68—C14—C16	123.0 (4)	C33—C32—H32	122.6
N68—C14—H14	118.5	C31—C32—H32	122.6
C16—C14—H14	118.5	C45—C46—C47	122.7 (10)
N69—C19—H19A	109.5	C45—C46—H46	118.7
N69—C19—H19B	109.5	C47—C46—H46	118.7
H19A—C19—H19B	109.5	C37—C38—C39	120.7 (10)
N69—C19—H19C	109.5	C37—C38—H38	119.7
H19A—C19—H19C	109.5	C39—C38—H38	119.7
H19B—C19—H19C	109.5	C46—C47—C48	118.3 (8)
C57—C58—C48	122.2 (5)	C46—C47—H47	120.9
C57—C58—C44	119.1 (6)	C48—C47—H47	120.9
C48—C58—C44	118.7 (7)	C51—C52—C53	124.4 (9)
C58—C57—C54	121.9 (6)	C51—C52—H52	117.8
C58—C57—C59	118.0 (6)	C53—C52—H52	117.8
C54—C57—C59	120.2 (6)	C29—C30—C31	119.5 (10)
C42—C41—C36	121.3 (6)	C29—C30—H30	120.3
C42—C41—C40	120.9 (7)	C31—C30—H30	120.3
C36—C41—C40	117.8 (7)	C30—C31—C32	123.5 (11)
N69—C18—H18A	109.5	C30—C31—H31	118.3
N69—C18—H18B	109.5	C32—C31—H31	118.3

(15NRES-TMP-DPE-I)

Crystal data

C40H46N8O8	Z = 1
Mr = 766.85	F(000) = 406
Triclinic, P1	Dx = 1.338 Mg m^−3
a = 7.5319 (7) Å	Mo Kα radiation, λ = 0.71075 Å
b = 8.6425 (8) Å	Cell parameters from 9035 reflections
c = 15.3925 (14) Å	θ = 3.0–27.5°
α = 78.729 (6)°	µ = 0.10 mm^−1
β = 75.782 (5)°	T = 150 K
γ = 89.099 (6)°	Block, yellow
V = 951.99 (15) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3565 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.023
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.887, Tmax = 1.000	k = −11→11
9956 measured reflections	l = −19→19
4348 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0593P)^2 + 0.3903P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.032
4348 reflections	Δρmax = 0.34 e Å^−3
257 parameters	Δρmin = −0.33 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O2	0.74232 (14)	0.39058 (12)	0.11433 (7)	0.0209 (2)
H2	0.656114	0.354233	0.100021	0.031*
O4	1.09634 (15)	0.60447 (14)	0.10504 (8)	0.0295 (3)
O1	0.90113 (15)	0.72439 (14)	0.28963 (8)	0.0291 (3)
H1	0.861090	0.783612	0.324982	0.044*
O3	1.05902 (15)	0.42111 (14)	0.22552 (8)	0.0319 (3)
N4	1.00179 (16)	0.52678 (14)	0.17525 (8)	0.0187 (3)
N2	0.79637 (17)	0.90020 (14)	0.41860 (9)	0.0212 (3)
N3	0.70851 (17)	1.09154 (15)	0.54523 (9)	0.0217 (3)
N1	0.47151 (17)	0.22009 (15)	0.08590 (9)	0.0223 (3)
C2	0.80734 (18)	0.56332 (16)	0.20322 (9)	0.0172 (3)
C3	0.7619 (2)	0.66648 (17)	0.26358 (10)	0.0202 (3)
C1	0.67929 (19)	0.49019 (16)	0.17162 (9)	0.0176 (3)
C6	0.4957 (2)	0.52497 (18)	0.20210 (10)	0.0216 (3)
H6	0.405532	0.478685	0.182706	0.026*
C8	0.80473 (19)	0.84553 (17)	0.50524 (10)	0.0209 (3)
C9	0.76027 (19)	0.94317 (18)	0.56908 (10)	0.0208 (3)
C19	0.15438 (19)	0.08327 (18)	0.06372 (10)	0.0195 (3)
C15	0.3473 (2)	0.30740 (18)	0.05113 (10)	0.0232 (3)
H15	0.368715	0.416089	0.034077	0.028*
C17	0.2838 (2)	−0.00883 (18)	0.09885 (10)	0.0229 (3)
H17	0.266533	−0.117947	0.115558	0.027*
C4	0.5774 (2)	0.70031 (18)	0.29286 (10)	0.0229 (3)
H4	0.541560	0.769534	0.332744	0.028*
C5	0.4486 (2)	0.62885 (18)	0.26140 (11)	0.0235 (3)
H5	0.325796	0.651604	0.280908	0.028*
C16	0.4379 (2)	0.06370 (19)	0.10860 (10)	0.0236 (3)
H16	0.522913	0.000599	0.132177	0.028*
C13	0.74639 (19)	1.04844 (17)	0.39377 (10)	0.0201 (3)
C12	0.70169 (19)	1.14479 (17)	0.45881 (10)	0.0203 (3)
C18	0.1893 (2)	0.24508 (18)	0.03924 (10)	0.0226 (3)
H18	0.107141	0.310915	0.015044	0.027*
C20	−0.0153 (2)	0.01207 (19)	0.04939 (10)	0.0225 (3)
H20A	−0.116916	0.081197	0.062692	0.027*
H20B	−0.046770	−0.088678	0.091195	0.027*
C14	0.7450 (2)	1.1043 (2)	0.29547 (11)	0.0291 (4)
H14A	0.791068	1.023800	0.261646	0.044*
H14B	0.821061	1.198464	0.270702	0.044*
H14C	0.621835	1.126606	0.291093	0.044*
C11	0.6494 (2)	1.31371 (18)	0.43376 (12)	0.0293 (4)
H11A	0.599114	1.353313	0.488462	0.044*
H11B	0.559710	1.318830	0.398559	0.044*
H11C	0.756146	1.376576	0.398295	0.044*
C7	0.8638 (2)	0.67898 (19)	0.52806 (13)	0.0311 (4)
H7A	0.759832	0.607622	0.541623	0.047*
H7B	0.914717	0.667003	0.580284	0.047*
H7C	0.954621	0.655764	0.476880	0.047*
C10	0.7688 (2)	0.8892 (2)	0.66667 (11)	0.0327 (4)
H10A	0.742964	0.975651	0.698146	0.049*
H10B	0.889008	0.852494	0.668499	0.049*
H10C	0.679746	0.804871	0.695820	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0170 (5)	0.0256 (5)	0.0241 (5)	−0.0004 (4)	−0.0073 (4)	−0.0118 (4)
O4	0.0213 (6)	0.0337 (6)	0.0277 (6)	−0.0007 (5)	0.0005 (5)	−0.0004 (5)
O1	0.0238 (6)	0.0347 (6)	0.0364 (6)	0.0000 (5)	−0.0096 (5)	−0.0225 (5)
O3	0.0214 (6)	0.0353 (7)	0.0361 (7)	0.0064 (5)	−0.0110 (5)	0.0045 (5)
N4	0.0172 (6)	0.0195 (6)	0.0219 (6)	−0.0010 (5)	−0.0072 (5)	−0.0072 (5)
N2	0.0203 (6)	0.0205 (6)	0.0241 (7)	−0.0016 (5)	−0.0063 (5)	−0.0061 (5)
N3	0.0206 (6)	0.0223 (6)	0.0215 (6)	−0.0002 (5)	−0.0034 (5)	−0.0047 (5)
N1	0.0192 (6)	0.0288 (7)	0.0216 (6)	−0.0025 (5)	−0.0066 (5)	−0.0092 (5)
C2	0.0143 (6)	0.0182 (7)	0.0194 (7)	0.0007 (5)	−0.0044 (5)	−0.0040 (5)
C3	0.0218 (7)	0.0192 (7)	0.0212 (7)	−0.0007 (5)	−0.0072 (6)	−0.0051 (5)
C1	0.0183 (7)	0.0179 (7)	0.0170 (7)	−0.0003 (5)	−0.0058 (5)	−0.0026 (5)
C6	0.0168 (7)	0.0241 (7)	0.0250 (7)	−0.0007 (5)	−0.0077 (6)	−0.0043 (6)
C8	0.0171 (7)	0.0190 (7)	0.0264 (8)	−0.0020 (5)	−0.0066 (6)	−0.0021 (6)
C9	0.0161 (7)	0.0241 (7)	0.0215 (7)	−0.0007 (5)	−0.0046 (5)	−0.0028 (6)
C19	0.0183 (7)	0.0254 (7)	0.0167 (7)	−0.0036 (5)	−0.0043 (5)	−0.0081 (5)
C15	0.0232 (7)	0.0225 (7)	0.0245 (8)	−0.0048 (6)	−0.0063 (6)	−0.0049 (6)
C17	0.0257 (8)	0.0215 (7)	0.0230 (7)	−0.0016 (6)	−0.0081 (6)	−0.0056 (6)
C4	0.0240 (8)	0.0209 (7)	0.0242 (8)	0.0033 (6)	−0.0040 (6)	−0.0079 (6)
C5	0.0161 (7)	0.0264 (8)	0.0256 (8)	0.0027 (6)	−0.0021 (6)	−0.0033 (6)
C16	0.0229 (7)	0.0284 (8)	0.0226 (7)	0.0023 (6)	−0.0092 (6)	−0.0082 (6)
C13	0.0184 (7)	0.0203 (7)	0.0223 (7)	−0.0034 (5)	−0.0066 (6)	−0.0032 (6)
C12	0.0167 (7)	0.0191 (7)	0.0241 (7)	−0.0006 (5)	−0.0046 (6)	−0.0026 (6)
C18	0.0225 (7)	0.0246 (8)	0.0224 (7)	−0.0018 (6)	−0.0089 (6)	−0.0046 (6)
C20	0.0190 (7)	0.0277 (8)	0.0224 (8)	−0.0066 (6)	−0.0060 (6)	−0.0071 (6)
C14	0.0338 (9)	0.0302 (8)	0.0246 (8)	−0.0026 (7)	−0.0120 (7)	−0.0019 (6)
C11	0.0308 (9)	0.0201 (8)	0.0365 (9)	0.0048 (6)	−0.0090 (7)	−0.0036 (6)
C7	0.0316 (9)	0.0210 (8)	0.0417 (10)	0.0047 (6)	−0.0128 (7)	−0.0037 (7)
C10	0.0347 (9)	0.0388 (10)	0.0237 (8)	0.0008 (7)	−0.0099 (7)	−0.0003 (7)

Geometric parameters (Å, º)

O2—C1	1.3500 (17)	C15—H15	0.9300
O2—H2	0.8200	C17—C16	1.381 (2)
O4—N4	1.2162 (16)	C17—H17	0.9300
O1—C3	1.3465 (17)	C4—C5	1.387 (2)
O1—H1	0.8200	C4—H4	0.9300
O3—N4	1.2223 (16)	C5—H5	0.9300
N4—C2	1.4693 (18)	C16—H16	0.9300
N2—C13	1.3391 (19)	C13—C12	1.400 (2)
N2—C8	1.3415 (19)	C13—C14	1.498 (2)
N3—C12	1.3331 (19)	C12—C11	1.507 (2)
N3—C9	1.3423 (19)	C18—H18	0.9300
N1—C16	1.340 (2)	C20—C20^i	1.536 (3)
N1—C15	1.341 (2)	C20—H20A	0.9700
C2—C3	1.390 (2)	C20—H20B	0.9700
C2—C1	1.3914 (19)	C14—H14A	0.9600
C3—C4	1.397 (2)	C14—H14B	0.9600
C1—C6	1.395 (2)	C14—H14C	0.9600
C6—C5	1.384 (2)	C11—H11A	0.9600
C6—H6	0.9300	C11—H11B	0.9600
C8—C9	1.394 (2)	C11—H11C	0.9600
C8—C7	1.501 (2)	C7—H7A	0.9600
C9—C10	1.500 (2)	C7—H7B	0.9600
C19—C18	1.387 (2)	C7—H7C	0.9600
C19—C17	1.394 (2)	C10—H10A	0.9600
C19—C20	1.5090 (19)	C10—H10B	0.9600
C15—C18	1.380 (2)	C10—H10C	0.9600
C1—O2—H2	109.5	N1—C16—H16	118.2
C3—O1—H1	109.5	C17—C16—H16	118.2
O4—N4—O3	124.07 (13)	N2—C13—C12	119.62 (13)
O4—N4—C2	118.56 (12)	N2—C13—C14	117.43 (13)
O3—N4—C2	117.36 (12)	C12—C13—C14	122.94 (14)
C13—N2—C8	119.87 (13)	N3—C12—C13	121.07 (13)
C12—N3—C9	118.73 (13)	N3—C12—C11	117.26 (13)
C16—N1—C15	116.70 (13)	C13—C12—C11	121.65 (14)
C3—C2—C1	123.72 (13)	C15—C18—C19	119.34 (14)
C3—C2—N4	116.85 (12)	C15—C18—H18	120.3
C1—C2—N4	119.38 (12)	C19—C18—H18	120.3
O1—C3—C2	116.59 (13)	C19—C20—C20^i	110.92 (15)
O1—C3—C4	125.43 (13)	C19—C20—H20A	109.5
C2—C3—C4	117.97 (13)	C20^i—C20—H20A	109.5
O2—C1—C2	117.47 (12)	C19—C20—H20B	109.5
O2—C1—C6	125.16 (13)	C20^i—C20—H20B	109.5
C2—C1—C6	117.37 (13)	H20A—C20—H20B	108.0
C5—C6—C1	119.55 (13)	C13—C14—H14A	109.5
C5—C6—H6	120.2	C13—C14—H14B	109.5
C1—C6—H6	120.2	H14A—C14—H14B	109.5
N2—C8—C9	119.78 (13)	C13—C14—H14C	109.5
N2—C8—C7	117.04 (14)	H14A—C14—H14C	109.5
C9—C8—C7	123.18 (14)	H14B—C14—H14C	109.5
N3—C9—C8	120.93 (13)	C12—C11—H11A	109.5
N3—C9—C10	116.87 (14)	C12—C11—H11B	109.5
C8—C9—C10	122.20 (14)	H11A—C11—H11B	109.5
C18—C19—C17	117.45 (13)	C12—C11—H11C	109.5
C18—C19—C20	120.28 (13)	H11A—C11—H11C	109.5
C17—C19—C20	122.23 (13)	H11B—C11—H11C	109.5
N1—C15—C18	123.69 (14)	C8—C7—H7A	109.5
N1—C15—H15	118.2	C8—C7—H7B	109.5
C18—C15—H15	118.2	H7A—C7—H7B	109.5
C16—C17—C19	119.28 (14)	C8—C7—H7C	109.5
C16—C17—H17	120.4	H7A—C7—H7C	109.5
C19—C17—H17	120.4	H7B—C7—H7C	109.5
C5—C4—C3	118.84 (14)	C9—C10—H10A	109.5
C5—C4—H4	120.6	C9—C10—H10B	109.5
C3—C4—H4	120.6	H10A—C10—H10B	109.5
C6—C5—C4	122.54 (14)	C9—C10—H10C	109.5
C6—C5—H5	118.7	H10A—C10—H10C	109.5
C4—C5—H5	118.7	H10B—C10—H10C	109.5
N1—C16—C17	123.52 (14)

Symmetry code: (i) −x, −y, −z.

(16NRES-TMP-22BP)

Crystal data

C38H42N8O8	Z = 1
Mr = 738.79	F(000) = 390
Triclinic, P1	Dx = 1.318 Mg m^−3
a = 7.4104 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8964 (9) Å	Cell parameters from 8594 reflections
c = 15.7722 (15) Å	θ = 3.0–27.5°
α = 95.531 (7)°	µ = 0.10 mm^−1
β = 101.446 (7)°	T = 150 K
γ = 111.676 (8)°	Block, yellow
V = 930.47 (17) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3261 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.027
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.850, Tmax = 1.000	k = −11→11
9757 measured reflections	l = −20→20
4270 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.0713P)^2 + 0.439P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
4270 reflections	Δρmax = 0.64 e Å^−3
248 parameters	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.6072 (2)	0.54850 (19)	0.39526 (11)	0.0435 (4)
O2	0.6668 (2)	0.75298 (18)	0.32810 (11)	0.0417 (4)
O3	0.33133 (19)	0.37213 (15)	0.21274 (9)	0.0304 (3)
H3	0.254544	0.297527	0.171892	0.046*
O4	0.36697 (18)	0.80485 (15)	0.41924 (8)	0.0280 (3)
H4	0.300636	0.852008	0.436226	0.042*
N4	0.5521 (2)	0.63146 (17)	0.34811 (9)	0.0228 (3)
C15	0.3358 (2)	0.5858 (2)	0.31408 (11)	0.0204 (3)
C16	0.2297 (3)	0.4542 (2)	0.24416 (11)	0.0221 (4)
C17	0.2482 (2)	0.6802 (2)	0.35159 (11)	0.0214 (4)
C18	0.0265 (3)	0.4174 (2)	0.20989 (12)	0.0261 (4)
H18	−0.048787	0.330866	0.162732	0.031*
C19	−0.0623 (3)	0.5108 (2)	0.24662 (12)	0.0260 (4)
H19	−0.197832	0.485379	0.223393	0.031*
C20	0.0443 (3)	0.6404 (2)	0.31671 (12)	0.0252 (4)
H20	−0.019211	0.700573	0.340390	0.030*
N1	0.0879 (2)	0.12529 (19)	0.07224 (10)	0.0289 (4)
C7	0.2525 (3)	0.3251 (2)	−0.01269 (15)	0.0401 (5)
H7A	0.266513	0.401110	0.038138	0.060*
H7B	0.193097	0.354556	−0.064817	0.060*
H7C	0.382217	0.328867	−0.015618	0.060*
C8	0.1197 (3)	0.1531 (2)	−0.00606 (13)	0.0294 (4)
C9	−0.0316 (3)	−0.0262 (2)	0.08106 (13)	0.0271 (4)
C10	−0.0658 (3)	−0.0514 (3)	0.16873 (13)	0.0362 (5)
H10A	−0.004228	0.052402	0.208802	0.054*
H10B	−0.007992	−0.125167	0.190118	0.054*
H10C	−0.207422	−0.097657	0.164242	0.054*
N2	0.5635 (2)	1.1208 (2)	0.10899 (11)	0.0312 (4)
C1	0.4262 (3)	0.9491 (3)	0.20808 (13)	0.0331 (4)
H1	0.413547	0.938380	0.264924	0.040*
C2	0.3378 (3)	0.8147 (3)	0.14009 (14)	0.0377 (5)
H2	0.260065	0.712103	0.150072	0.045*
C3	0.3657 (3)	0.8337 (2)	0.05689 (13)	0.0315 (4)
H3A	0.307894	0.744201	0.010436	0.038*
C4	0.4808 (2)	0.9877 (2)	0.04417 (11)	0.0240 (4)
C5	0.5335 (3)	1.0991 (2)	0.18930 (13)	0.0313 (4)
H5	0.588433	1.190728	0.234447	0.038*
N3	0.1436 (2)	0.94649 (17)	0.48337 (9)	0.0216 (3)
C11	0.0386 (3)	0.7194 (2)	0.56171 (14)	0.0334 (4)
H11A	0.154265	0.708107	0.548174	0.050*
H11B	−0.079137	0.622377	0.533187	0.050*
H11C	0.054573	0.733242	0.624250	0.050*
C12	0.0171 (3)	0.8669 (2)	0.52969 (11)	0.0223 (4)
C13	0.1294 (3)	1.0790 (2)	0.45359 (11)	0.0221 (4)
C14	0.2786 (3)	1.1669 (2)	0.40453 (13)	0.0307 (4)
H14A	0.358103	1.277334	0.436110	0.046*
H14B	0.208699	1.169920	0.346960	0.046*
H14C	0.364376	1.109819	0.399134	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0278 (7)	0.0473 (9)	0.0535 (9)	0.0152 (7)	−0.0007 (7)	0.0215 (7)
O2	0.0198 (7)	0.0404 (8)	0.0657 (10)	0.0089 (6)	0.0138 (7)	0.0195 (7)
O3	0.0257 (7)	0.0276 (7)	0.0330 (7)	0.0119 (6)	0.0022 (5)	−0.0106 (5)
O4	0.0212 (6)	0.0301 (7)	0.0296 (7)	0.0118 (5)	0.0032 (5)	−0.0084 (5)
N4	0.0187 (7)	0.0233 (7)	0.0253 (7)	0.0093 (6)	0.0047 (6)	−0.0022 (6)
C15	0.0156 (7)	0.0214 (8)	0.0228 (8)	0.0068 (6)	0.0038 (6)	0.0020 (6)
C16	0.0224 (8)	0.0200 (8)	0.0237 (8)	0.0083 (7)	0.0067 (7)	0.0013 (6)
C17	0.0199 (8)	0.0204 (8)	0.0228 (8)	0.0074 (7)	0.0061 (7)	0.0011 (6)
C18	0.0220 (8)	0.0221 (8)	0.0274 (9)	0.0049 (7)	0.0011 (7)	−0.0002 (7)
C19	0.0158 (8)	0.0271 (9)	0.0318 (9)	0.0064 (7)	0.0035 (7)	0.0043 (7)
C20	0.0201 (8)	0.0270 (9)	0.0310 (9)	0.0119 (7)	0.0076 (7)	0.0033 (7)
N1	0.0267 (8)	0.0291 (8)	0.0291 (8)	0.0123 (7)	0.0039 (6)	−0.0016 (6)
C7	0.0453 (12)	0.0266 (10)	0.0401 (12)	0.0048 (9)	0.0136 (10)	0.0016 (8)
C8	0.0274 (9)	0.0350 (10)	0.0320 (10)	0.0175 (8)	0.0098 (8)	0.0095 (8)
C9	0.0209 (8)	0.0246 (9)	0.0354 (10)	0.0115 (7)	0.0027 (7)	0.0026 (7)
C10	0.0387 (11)	0.0426 (12)	0.0296 (10)	0.0198 (10)	0.0075 (8)	0.0044 (9)
N2	0.0270 (8)	0.0310 (8)	0.0308 (8)	0.0078 (7)	0.0038 (7)	0.0065 (7)
C1	0.0324 (10)	0.0416 (11)	0.0300 (10)	0.0167 (9)	0.0117 (8)	0.0117 (8)
C2	0.0415 (11)	0.0325 (11)	0.0373 (11)	0.0096 (9)	0.0120 (9)	0.0155 (9)
C3	0.0358 (10)	0.0255 (9)	0.0296 (10)	0.0085 (8)	0.0073 (8)	0.0058 (7)
C4	0.0176 (8)	0.0269 (9)	0.0280 (9)	0.0091 (7)	0.0045 (7)	0.0091 (7)
C5	0.0310 (10)	0.0346 (10)	0.0272 (9)	0.0132 (8)	0.0047 (8)	0.0057 (8)
N3	0.0237 (7)	0.0212 (7)	0.0189 (7)	0.0095 (6)	0.0041 (5)	−0.0009 (5)
C11	0.0394 (11)	0.0293 (10)	0.0372 (11)	0.0188 (9)	0.0097 (9)	0.0111 (8)
C12	0.0248 (8)	0.0211 (8)	0.0185 (8)	0.0082 (7)	0.0032 (6)	0.0005 (6)
C13	0.0253 (8)	0.0205 (8)	0.0181 (8)	0.0083 (7)	0.0042 (6)	−0.0011 (6)
C14	0.0331 (10)	0.0319 (10)	0.0291 (10)	0.0117 (8)	0.0136 (8)	0.0079 (8)

Geometric parameters (Å, º)

O1—N4	1.213 (2)	C8—C9^i	1.412 (3)
O2—N4	1.218 (2)	C9—C10	1.478 (3)
O3—C16	1.353 (2)	N2—C4	1.344 (2)
O4—C17	1.349 (2)	N2—C5	1.348 (2)
N4—C15	1.469 (2)	C1—C5	1.374 (3)
C15—C16	1.390 (2)	C1—C2	1.380 (3)
C15—C17	1.392 (2)	C2—C3	1.385 (3)
C16—C18	1.394 (2)	C3—C4	1.379 (3)
C17—C20	1.396 (2)	C4—C4^ii	1.497 (3)
C18—C19	1.386 (3)	N3—C12	1.340 (2)
C19—C20	1.382 (3)	N3—C13	1.342 (2)
N1—C8	1.332 (2)	C11—C12	1.502 (2)
N1—C9	1.350 (2)	C12—C13^iii	1.398 (2)
C7—C8	1.509 (3)	C13—C14	1.500 (2)
O1—N4—O2	123.57 (15)	N1—C9—C8^i	118.63 (17)
O1—N4—C15	118.77 (15)	N1—C9—C10	118.49 (17)
O2—N4—C15	117.65 (14)	C8^i—C9—C10	122.88 (18)
C16—C15—C17	123.10 (15)	C4—N2—C5	117.49 (16)
C16—C15—N4	118.63 (14)	C5—C1—C2	118.02 (18)
C17—C15—N4	118.23 (14)	C1—C2—C3	119.53 (19)
O3—C16—C15	117.79 (15)	C4—C3—C2	118.79 (18)
O3—C16—C18	124.29 (15)	N2—C4—C3	122.52 (17)
C15—C16—C18	117.91 (15)	N2—C4—C4^ii	117.07 (19)
O4—C17—C15	117.56 (14)	C3—C4—C4^ii	120.4 (2)
O4—C17—C20	124.41 (15)	N2—C5—C1	123.59 (18)
C15—C17—C20	118.03 (15)	C12—N3—C13	119.53 (15)
C19—C18—C16	119.51 (16)	N3—C12—C13^iii	120.24 (15)
C20—C19—C18	122.07 (16)	N3—C12—C11	117.65 (15)
C19—C20—C17	119.37 (16)	C13^iii—C12—C11	122.11 (16)
C8—N1—C9	120.16 (16)	N3—C13—C12^iii	120.23 (16)
N1—C8—C9^i	121.21 (18)	N3—C13—C14	117.49 (15)
N1—C8—C7	118.12 (17)	C12^iii—C13—C14	122.27 (16)
C9^i—C8—C7	120.67 (18)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+2, −z; (iii) −x, −y+2, −z+1.

(17NRE-TMP-22TBP)

Crystal data

C22H23N3O4S2	Z = 2
Mr = 457.55	F(000) = 480
Triclinic, P1	Dx = 1.371 Mg m^−3
a = 7.6512 (11) Å	Mo Kα radiation, λ = 0.71075 Å
b = 8.9495 (13) Å	Cell parameters from 9432 reflections
c = 18.121 (3) Å	θ = 3.0–27.7°
α = 87.883 (6)°	µ = 0.27 mm^−1
β = 78.725 (6)°	T = 150 K
γ = 65.728 (5)°	Block, colorless
V = 1108.0 (3) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3698 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.039
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.805, Tmax = 1.000	k = −11→11
11118 measured reflections	l = −23→23
5059 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.206	w = 1/[σ^2(Fo^2) + (0.1022P)^2 + 1.3547P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
5059 reflections	Δρmax = 0.93 e Å^−3
286 parameters	Δρmin = −0.79 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S2	1.09372 (13)	−0.15221 (11)	0.59467 (5)	0.0363 (3)
S1	0.77371 (16)	0.24729 (13)	1.00457 (7)	0.0509 (3)
O1	0.3983 (3)	0.3740 (3)	0.64814 (13)	0.0288 (5)
H1	0.401961	0.314966	0.613782	0.043*
O2	−0.0179 (3)	0.7223 (3)	0.85409 (12)	0.0285 (5)
H2	−0.129666	0.758699	0.878993	0.043*
O4	0.4648 (3)	0.4560 (3)	0.79685 (15)	0.0378 (6)
N2	0.3433 (3)	0.5694 (3)	0.77070 (13)	0.0195 (5)
N1	0.6362 (3)	0.8868 (3)	0.94558 (13)	0.0184 (5)
O3	0.3512 (4)	0.7021 (3)	0.76095 (17)	0.0431 (7)
N3	0.4442 (3)	0.1301 (3)	0.55041 (13)	0.0219 (5)
C20	1.0204 (4)	0.0623 (3)	0.89161 (16)	0.0204 (6)
H20	1.118317	−0.025764	0.861618	0.024*
C2	0.1796 (4)	0.5466 (3)	0.75046 (15)	0.0171 (5)
C9	0.5137 (4)	1.0333 (3)	0.92630 (16)	0.0197 (6)
C1	−0.0056 (4)	0.6289 (3)	0.79521 (16)	0.0196 (6)
C8	0.6242 (4)	0.8510 (3)	1.01825 (15)	0.0187 (6)
C6	−0.1620 (4)	0.6081 (3)	0.77621 (16)	0.0214 (6)
H6	−0.287371	0.660846	0.804963	0.026*
C3	0.2144 (4)	0.4446 (3)	0.68839 (16)	0.0209 (6)
C13	0.4317 (4)	0.1561 (4)	0.47811 (16)	0.0226 (6)
C12	0.5110 (4)	−0.0244 (4)	0.57306 (16)	0.0227 (6)
C4	0.0552 (4)	0.4263 (4)	0.66999 (17)	0.0247 (6)
H4	0.072658	0.359818	0.628518	0.030*
C5	−0.1288 (4)	0.5080 (4)	0.71407 (17)	0.0236 (6)
H5	−0.234087	0.495167	0.701443	0.028*
C16	0.8646 (5)	0.1493 (4)	0.58579 (18)	0.0286 (7)
H16	0.792347	0.249906	0.567610	0.034*
C7	0.7596 (4)	0.6845 (4)	1.03695 (17)	0.0260 (6)
H7A	0.832741	0.619946	0.991235	0.039*
H7B	0.684922	0.631526	1.066419	0.039*
H7C	0.848053	0.695277	1.065196	0.039*
C15	0.9822 (4)	0.0104 (4)	0.54077 (18)	0.0257 (6)
C17	0.8665 (5)	0.1210 (4)	0.6639 (2)	0.0326 (7)
H17	0.793850	0.201264	0.702255	0.039*
C10	0.5312 (5)	1.0644 (4)	0.84435 (17)	0.0302 (7)
H10A	0.636932	0.971850	0.816076	0.045*
H10B	0.556333	1.160698	0.835004	0.045*
H10C	0.411405	1.080673	0.829204	0.045*
C18	0.9843 (5)	−0.0340 (4)	0.6762 (2)	0.0339 (7)
H18	1.003702	−0.072142	0.723678	0.041*
C11	0.5196 (5)	−0.0479 (4)	0.65492 (17)	0.0329 (7)
H11A	0.490447	0.055316	0.679365	0.049*
H11B	0.648268	−0.124784	0.659618	0.049*
H11C	0.425508	−0.089300	0.678130	0.049*
C14	0.3532 (5)	0.3308 (4)	0.4552 (2)	0.0363 (8)
H14A	0.320684	0.403131	0.498395	0.054*
H14B	0.238248	0.354230	0.434975	0.054*
H14C	0.450652	0.346831	0.417641	0.054*
C19	0.9611 (5)	0.0636 (4)	0.9744 (2)	0.0327 (7)
C22	0.7748 (7)	0.3176 (5)	0.9174 (3)	0.0617 (14)
H22	0.689373	0.421302	0.906609	0.074*
C21	0.9102 (9)	0.2096 (7)	0.8658 (3)	0.0670 (15)
H21	0.929119	0.232568	0.815078	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S2	0.0316 (4)	0.0284 (4)	0.0374 (5)	−0.0022 (3)	−0.0046 (3)	0.0073 (3)
S1	0.0463 (6)	0.0443 (6)	0.0662 (7)	−0.0189 (5)	−0.0213 (5)	0.0113 (5)
O1	0.0197 (10)	0.0316 (12)	0.0296 (12)	−0.0081 (9)	0.0050 (8)	−0.0168 (9)
O2	0.0180 (10)	0.0364 (13)	0.0264 (11)	−0.0090 (9)	0.0044 (8)	−0.0162 (9)
O4	0.0313 (12)	0.0367 (13)	0.0522 (15)	−0.0157 (11)	−0.0229 (11)	0.0196 (11)
N2	0.0152 (11)	0.0206 (12)	0.0189 (12)	−0.0047 (9)	−0.0003 (9)	−0.0004 (9)
N1	0.0172 (11)	0.0172 (11)	0.0180 (12)	−0.0054 (9)	0.0000 (9)	−0.0030 (9)
O3	0.0330 (13)	0.0276 (13)	0.079 (2)	−0.0184 (11)	−0.0216 (13)	0.0135 (13)
N3	0.0209 (12)	0.0235 (12)	0.0184 (12)	−0.0070 (10)	−0.0013 (9)	−0.0039 (9)
C20	0.0359 (16)	0.0151 (13)	0.0201 (13)	−0.0192 (12)	−0.0077 (12)	−0.0007 (10)
C2	0.0134 (12)	0.0179 (13)	0.0187 (13)	−0.0058 (10)	−0.0020 (10)	0.0005 (10)
C9	0.0193 (13)	0.0195 (13)	0.0199 (14)	−0.0082 (11)	−0.0016 (10)	−0.0024 (11)
C1	0.0180 (13)	0.0164 (13)	0.0204 (14)	−0.0043 (10)	−0.0003 (10)	−0.0023 (10)
C8	0.0150 (12)	0.0178 (13)	0.0205 (14)	−0.0045 (10)	−0.0016 (10)	−0.0024 (10)
C6	0.0137 (12)	0.0201 (14)	0.0258 (15)	−0.0038 (11)	−0.0004 (11)	−0.0008 (11)
C3	0.0167 (13)	0.0201 (14)	0.0218 (14)	−0.0055 (11)	0.0012 (10)	−0.0021 (11)
C13	0.0219 (14)	0.0238 (15)	0.0203 (14)	−0.0078 (11)	−0.0036 (11)	0.0007 (11)
C12	0.0210 (14)	0.0287 (15)	0.0187 (14)	−0.0107 (12)	−0.0031 (11)	0.0009 (12)
C4	0.0236 (14)	0.0259 (15)	0.0237 (15)	−0.0097 (12)	−0.0018 (11)	−0.0083 (12)
C5	0.0192 (13)	0.0247 (15)	0.0280 (15)	−0.0094 (12)	−0.0059 (11)	0.0011 (12)
C16	0.0267 (15)	0.0244 (15)	0.0343 (17)	−0.0099 (13)	−0.0067 (13)	0.0014 (13)
C7	0.0240 (15)	0.0206 (14)	0.0270 (16)	−0.0026 (12)	−0.0051 (12)	−0.0001 (12)
C15	0.0187 (14)	0.0252 (15)	0.0331 (17)	−0.0085 (12)	−0.0069 (12)	0.0067 (12)
C17	0.0359 (18)	0.0313 (17)	0.0335 (18)	−0.0170 (14)	−0.0058 (14)	0.0006 (14)
C10	0.0334 (17)	0.0317 (17)	0.0190 (15)	−0.0082 (14)	−0.0023 (12)	0.0002 (12)
C18	0.0335 (17)	0.0350 (18)	0.0341 (18)	−0.0153 (15)	−0.0070 (14)	0.0073 (14)
C11	0.0452 (19)	0.0401 (19)	0.0172 (15)	−0.0203 (16)	−0.0089 (13)	0.0020 (13)
C14	0.044 (2)	0.0275 (17)	0.0332 (18)	−0.0086 (15)	−0.0116 (15)	0.0019 (14)
C19	0.0405 (18)	0.0281 (17)	0.0420 (19)	−0.0208 (15)	−0.0223 (15)	0.0093 (14)
C22	0.067 (3)	0.037 (2)	0.107 (4)	−0.028 (2)	−0.063 (3)	0.029 (3)
C21	0.119 (5)	0.069 (3)	0.054 (3)	−0.066 (4)	−0.053 (3)	0.029 (3)

Geometric parameters (Å, º)

S2—C18	1.705 (4)	C13—C14	1.502 (4)
S2—C15	1.732 (3)	C12—C11	1.501 (4)
S1—C22	1.678 (5)	C4—C5	1.382 (4)
S1—C19	1.697 (4)	C4—H4	0.9300
O1—C3	1.346 (3)	C5—H5	0.9300
O1—H1	0.8200	C16—C15	1.374 (4)
O2—C1	1.345 (3)	C16—C17	1.431 (5)
O2—H2	0.8200	C16—H16	0.9300
O4—N2	1.216 (3)	C7—H7A	0.9600
N2—O3	1.219 (3)	C7—H7B	0.9600
N2—C2	1.463 (3)	C7—H7C	0.9600
N1—C8	1.338 (4)	C15—C15^iii	1.454 (6)
N1—C9	1.342 (4)	C17—C18	1.347 (5)
N3—C13	1.337 (4)	C17—H17	0.9300
N3—C12	1.342 (4)	C10—H10A	0.9600
C20—C21	1.365 (6)	C10—H10B	0.9600
C20—C19	1.479 (5)	C10—H10C	0.9600
C20—H20	0.9300	C18—H18	0.9300
C2—C3	1.389 (4)	C11—H11A	0.9600
C2—C1	1.394 (4)	C11—H11B	0.9600
C9—C8^i	1.400 (4)	C11—H11C	0.9600
C9—C10	1.491 (4)	C14—H14A	0.9600
C1—C6	1.390 (4)	C14—H14B	0.9600
C8—C7	1.497 (4)	C14—H14C	0.9600
C6—C5	1.382 (4)	C19—C19^iv	1.446 (6)
C6—H6	0.9300	C22—C21	1.322 (8)
C3—C4	1.396 (4)	C22—H22	0.9300
C13—C12^ii	1.392 (4)	C21—H21	0.9300
C18—S2—C15	92.07 (16)	C17—C16—H16	124.0
C22—S1—C19	93.1 (2)	C8—C7—H7A	109.5
C3—O1—H1	109.5	C8—C7—H7B	109.5
C1—O2—H2	109.5	H7A—C7—H7B	109.5
O4—N2—O3	122.8 (3)	C8—C7—H7C	109.5
O4—N2—C2	118.9 (2)	H7A—C7—H7C	109.5
O3—N2—C2	118.3 (2)	H7B—C7—H7C	109.5
C8—N1—C9	119.6 (2)	C16—C15—C15^iii	128.5 (4)
C13—N3—C12	119.1 (3)	C16—C15—S2	110.7 (2)
C21—C20—C19	109.9 (3)	C15^iii—C15—S2	120.8 (3)
C21—C20—H20	125.0	C18—C17—C16	113.0 (3)
C19—C20—H20	125.0	C18—C17—H17	123.5
C3—C2—C1	123.0 (3)	C16—C17—H17	123.5
C3—C2—N2	119.1 (2)	C9—C10—H10A	109.5
C1—C2—N2	117.9 (2)	C9—C10—H10B	109.5
N1—C9—C8^i	120.4 (3)	H10A—C10—H10B	109.5
N1—C9—C10	117.1 (2)	C9—C10—H10C	109.5
C8^i—C9—C10	122.5 (3)	H10A—C10—H10C	109.5
O2—C1—C6	125.1 (2)	H10B—C10—H10C	109.5
O2—C1—C2	116.7 (2)	C17—C18—S2	112.2 (3)
C6—C1—C2	118.2 (3)	C17—C18—H18	123.9
N1—C8—C9^i	120.0 (2)	S2—C18—H18	123.9
N1—C8—C7	117.8 (2)	C12—C11—H11A	109.5
C9^i—C8—C7	122.2 (3)	C12—C11—H11B	109.5
C5—C6—C1	119.2 (3)	H11A—C11—H11B	109.5
C5—C6—H6	120.4	C12—C11—H11C	109.5
C1—C6—H6	120.4	H11A—C11—H11C	109.5
O1—C3—C2	118.0 (2)	H11B—C11—H11C	109.5
O1—C3—C4	124.0 (3)	C13—C14—H14A	109.5
C2—C3—C4	117.9 (2)	C13—C14—H14B	109.5
N3—C13—C12^ii	120.4 (3)	H14A—C14—H14B	109.5
N3—C13—C14	117.5 (3)	C13—C14—H14C	109.5
C12^ii—C13—C14	122.1 (3)	H14A—C14—H14C	109.5
N3—C12—C13^ii	120.5 (3)	H14B—C14—H14C	109.5
N3—C12—C11	117.4 (3)	C19^iv—C19—C20	129.2 (4)
C13^ii—C12—C11	122.1 (3)	C19^iv—C19—S1	122.2 (4)
C5—C4—C3	119.3 (3)	C20—C19—S1	108.5 (2)
C5—C4—H4	120.3	C21—C22—S1	112.7 (3)
C3—C4—H4	120.3	C21—C22—H22	123.6
C6—C5—C4	122.4 (3)	S1—C22—H22	123.6
C6—C5—H5	118.8	C22—C21—C20	115.7 (4)
C4—C5—H5	118.8	C22—C21—H21	122.2
C15—C16—C17	112.1 (3)	C20—C21—H21	122.2
C15—C16—H16	124.0

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+1, −y, −z+1; (iii) −x+2, −y, −z+1; (iv) −x+2, −y, −z+2.

(18NRES-TMP-PYR-ACR)

Crystal data

C62H50N6O8	Z = 1
Mr = 1007.08	F(000) = 528
Triclinic, P1	Dx = 1.379 Mg m^−3
a = 7.6840 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.266 (2) Å	Cell parameters from 8502 reflections
c = 18.043 (4) Å	θ = 3.0–28.2°
α = 96.343 (7)°	µ = 0.09 mm^−1
β = 94.419 (7)°	T = 150 K
γ = 107.054 (7)°	Block, yellow
V = 1212.6 (5) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2857 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.092
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.600, Tmax = 1.000	k = −12→12
12080 measured reflections	l = −23→23
5501 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.086	w = 1/[σ^2(Fo^2) + (0.1336P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.254	(Δ/σ)max < 0.001
S = 0.95	Δρmax = 0.60 e Å^−3
5501 reflections	Δρmin = −0.52 e Å^−3
348 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.008 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C12	0.3986 (4)	−0.0782 (4)	0.62510 (17)	0.0294 (8)
H12	0.472191	0.000707	0.660698	0.035*
C4	0.1211 (5)	0.2104 (4)	0.35485 (18)	0.0328 (8)
H4	0.073186	0.236607	0.311209	0.039*
N1	0.3446 (3)	0.1032 (3)	0.54927 (13)	0.0231 (6)
C23	0.4342 (5)	0.1425 (4)	0.85978 (18)	0.0332 (8)
H23	0.459398	0.233810	0.839840	0.040*
O2	0.8896 (3)	0.6054 (3)	0.86315 (12)	0.0344 (6)
H2A	0.879897	0.676527	0.892198	0.052*
O1	0.6141 (3)	0.2941 (3)	0.63979 (12)	0.0317 (6)
H1	0.516177	0.251094	0.613858	0.048*
N3	0.9075 (3)	0.4172 (3)	0.73826 (13)	0.0249 (6)
C28	−0.1367 (5)	−0.0178 (4)	0.84754 (17)	0.0352 (8)
H28A	−0.173519	−0.122267	0.824530	0.053*
H28B	−0.043804	0.042202	0.821257	0.053*
H28C	−0.240661	0.019725	0.845378	0.053*
C31	0.0661 (5)	0.2799 (4)	0.94073 (18)	0.0361 (8)
H31A	0.117229	0.362262	0.980953	0.054*
H31B	−0.046056	0.288971	0.917377	0.054*
H31C	0.151463	0.283702	0.904306	0.054*
N2	−0.0884 (3)	−0.1366 (3)	0.95681 (14)	0.0281 (6)
C5	0.0873 (4)	0.0624 (4)	0.36312 (17)	0.0311 (8)
H5	0.015253	−0.012216	0.325228	0.037*
O3	1.0112 (3)	0.5027 (3)	0.70384 (15)	0.0510 (8)
O4	0.9380 (3)	0.3068 (3)	0.75920 (15)	0.0472 (7)
C13	0.3170 (4)	−0.0428 (4)	0.55916 (16)	0.0241 (7)
C27	0.4649 (4)	0.0021 (4)	0.96269 (16)	0.0248 (7)
C7	0.1316 (4)	−0.1305 (4)	0.43997 (16)	0.0256 (7)
H7	0.059828	−0.208483	0.403479	0.031*
C30	0.0283 (4)	0.1321 (4)	0.97105 (16)	0.0270 (7)
C29	−0.0624 (4)	−0.0071 (4)	0.92751 (17)	0.0267 (7)
C22	0.5044 (4)	0.1417 (4)	0.93314 (17)	0.0274 (7)
C19	0.5855 (4)	0.3765 (3)	0.70048 (16)	0.0236 (7)
C1	0.2699 (4)	0.1364 (4)	0.48630 (17)	0.0246 (7)
C9	0.1869 (4)	−0.3169 (4)	0.51880 (18)	0.0307 (8)
H9	0.118181	−0.398006	0.483194	0.037*
C8	0.2082 (4)	−0.1667 (4)	0.50465 (17)	0.0251 (7)
C18	0.4211 (4)	0.4007 (4)	0.71390 (17)	0.0276 (7)
H18	0.316017	0.354034	0.680521	0.033*
C6	0.1596 (4)	0.0185 (4)	0.42869 (16)	0.0247 (7)
C2	0.3011 (4)	0.2905 (4)	0.47550 (18)	0.0284 (7)
H2	0.371873	0.367865	0.512493	0.034*
C11	0.3724 (5)	−0.2223 (4)	0.63741 (18)	0.0348 (8)
H11	0.425175	−0.242226	0.681754	0.042*
C14	0.7368 (4)	0.4466 (3)	0.75300 (16)	0.0217 (7)
C3	0.2289 (5)	0.3264 (4)	0.41188 (18)	0.0306 (8)
H3	0.250277	0.428119	0.405568	0.037*
C15	0.7318 (4)	0.5427 (3)	0.81698 (16)	0.0261 (7)
C26	0.3542 (4)	−0.1348 (4)	0.91779 (17)	0.0285 (7)
C17	0.4155 (5)	0.4958 (4)	0.77792 (18)	0.0309 (8)
H17	0.304575	0.511924	0.786842	0.037*
C25	0.2879 (4)	−0.1268 (4)	0.84461 (17)	0.0323 (8)
H25	0.215534	−0.215379	0.814509	0.039*
C10	0.2642 (5)	−0.3454 (4)	0.58304 (19)	0.0359 (8)
H10	0.246834	−0.445483	0.591775	0.043*
C16	0.5679 (4)	0.5676 (4)	0.82901 (17)	0.0296 (8)
H16	0.559735	0.632003	0.871055	0.036*
C20	0.6839 (4)	0.2734 (4)	1.05002 (19)	0.0330 (8)
H20	0.757635	0.363433	1.078588	0.040*
C21	0.6163 (5)	0.2772 (4)	0.97978 (19)	0.0331 (8)
H21	0.642640	0.369797	0.960994	0.040*
C24	0.3273 (5)	0.0089 (4)	0.81623 (18)	0.0356 (8)
H24	0.281728	0.011148	0.767246	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C12	0.0340 (18)	0.0346 (19)	0.0188 (15)	0.0101 (15)	0.0031 (14)	0.0007 (14)
C4	0.043 (2)	0.038 (2)	0.0195 (16)	0.0155 (16)	0.0005 (15)	0.0070 (15)
N1	0.0268 (13)	0.0226 (14)	0.0168 (12)	0.0053 (11)	−0.0003 (11)	−0.0019 (11)
C23	0.039 (2)	0.035 (2)	0.0276 (18)	0.0142 (16)	0.0049 (16)	0.0071 (16)
O2	0.0346 (13)	0.0311 (14)	0.0281 (12)	0.0077 (10)	−0.0128 (10)	−0.0179 (10)
O1	0.0302 (12)	0.0329 (13)	0.0220 (12)	0.0029 (10)	−0.0049 (10)	−0.0144 (10)
N3	0.0306 (15)	0.0227 (14)	0.0164 (13)	0.0049 (12)	−0.0050 (11)	−0.0039 (11)
C28	0.045 (2)	0.034 (2)	0.0226 (17)	0.0120 (16)	−0.0039 (15)	−0.0069 (15)
C31	0.050 (2)	0.0283 (19)	0.0254 (17)	0.0076 (16)	0.0003 (16)	0.0011 (15)
N2	0.0332 (15)	0.0264 (15)	0.0182 (13)	0.0042 (12)	−0.0029 (12)	−0.0073 (11)
C5	0.0325 (18)	0.036 (2)	0.0199 (16)	0.0072 (15)	−0.0015 (14)	−0.0032 (15)
O3	0.0393 (15)	0.0627 (19)	0.0620 (18)	0.0193 (14)	0.0224 (14)	0.0327 (16)
O4	0.0473 (15)	0.0385 (16)	0.0638 (18)	0.0222 (13)	0.0077 (14)	0.0155 (14)
C13	0.0288 (17)	0.0245 (17)	0.0169 (15)	0.0076 (13)	0.0012 (13)	−0.0034 (13)
C27	0.0273 (16)	0.0281 (18)	0.0194 (16)	0.0102 (14)	0.0043 (14)	−0.0007 (14)
C7	0.0265 (16)	0.0246 (17)	0.0199 (15)	0.0035 (13)	−0.0011 (13)	−0.0070 (13)
C30	0.0313 (17)	0.0305 (18)	0.0175 (15)	0.0092 (14)	0.0017 (13)	−0.0020 (14)
C29	0.0331 (18)	0.0275 (18)	0.0165 (15)	0.0086 (14)	0.0011 (13)	−0.0059 (13)
C22	0.0300 (17)	0.0298 (18)	0.0226 (16)	0.0096 (14)	0.0056 (14)	0.0013 (14)
C19	0.0308 (17)	0.0180 (16)	0.0178 (15)	0.0051 (13)	−0.0021 (13)	−0.0049 (12)
C1	0.0251 (16)	0.0273 (17)	0.0195 (15)	0.0069 (13)	0.0020 (13)	−0.0023 (13)
C9	0.0359 (18)	0.0226 (17)	0.0306 (18)	0.0052 (14)	0.0085 (15)	−0.0025 (14)
C8	0.0270 (16)	0.0232 (17)	0.0217 (16)	0.0051 (13)	0.0036 (13)	−0.0048 (13)
C18	0.0294 (17)	0.0234 (17)	0.0242 (16)	0.0040 (14)	−0.0078 (13)	−0.0027 (13)
C6	0.0256 (16)	0.0280 (17)	0.0168 (15)	0.0053 (13)	0.0011 (13)	−0.0038 (13)
C2	0.0314 (17)	0.0251 (17)	0.0256 (17)	0.0054 (14)	0.0038 (14)	−0.0009 (14)
C11	0.044 (2)	0.042 (2)	0.0243 (17)	0.0197 (17)	0.0061 (16)	0.0101 (16)
C14	0.0229 (15)	0.0186 (15)	0.0193 (15)	0.0021 (12)	−0.0008 (12)	−0.0018 (12)
C3	0.0405 (19)	0.0250 (18)	0.0282 (17)	0.0120 (15)	0.0058 (15)	0.0052 (14)
C15	0.0299 (17)	0.0211 (16)	0.0205 (16)	0.0032 (13)	−0.0086 (13)	−0.0053 (13)
C26	0.0300 (17)	0.0329 (19)	0.0222 (16)	0.0112 (14)	0.0034 (14)	−0.0028 (14)
C17	0.0314 (18)	0.0293 (18)	0.0294 (17)	0.0085 (15)	0.0005 (15)	−0.0019 (15)
C25	0.0332 (18)	0.039 (2)	0.0185 (16)	0.0073 (16)	−0.0037 (14)	−0.0090 (15)
C10	0.049 (2)	0.0282 (19)	0.0356 (19)	0.0166 (17)	0.0136 (18)	0.0065 (16)
C16	0.0342 (18)	0.0261 (18)	0.0233 (16)	0.0080 (14)	−0.0044 (14)	−0.0101 (14)
C20	0.0333 (19)	0.0269 (18)	0.0318 (18)	0.0029 (15)	0.0025 (15)	−0.0069 (15)
C21	0.0385 (19)	0.0267 (18)	0.0346 (19)	0.0109 (15)	0.0064 (16)	0.0025 (15)
C24	0.039 (2)	0.049 (2)	0.0192 (16)	0.0163 (17)	0.0002 (15)	0.0025 (16)

Geometric parameters (Å, º)

C12—C11	1.337 (5)	C27—C26	1.422 (4)
C12—C13	1.417 (4)	C7—C6	1.375 (4)
C4—C5	1.346 (5)	C7—C8	1.385 (4)
C4—C3	1.415 (5)	C30—C29	1.390 (4)
N1—C1	1.340 (4)	C22—C21	1.431 (5)
N1—C13	1.341 (4)	C19—C18	1.380 (4)
C23—C24	1.384 (5)	C19—C14	1.387 (4)
C23—C22	1.392 (4)	C1—C2	1.415 (4)
O2—C15	1.351 (3)	C1—C6	1.436 (4)
O1—C19	1.335 (3)	C9—C10	1.349 (5)
N3—O4	1.207 (3)	C9—C8	1.407 (4)
N3—O3	1.210 (3)	C18—C17	1.385 (4)
N3—C14	1.454 (4)	C2—C3	1.353 (4)
C28—C29	1.492 (4)	C11—C10	1.423 (5)
C31—C30	1.488 (4)	C14—C15	1.388 (4)
N2—C29	1.332 (4)	C15—C16	1.374 (4)
N2—C30^i	1.339 (4)	C26—C25	1.396 (4)
C5—C6	1.418 (4)	C26—C20^ii	1.430 (4)
C13—C8	1.430 (4)	C17—C16	1.380 (4)
C27—C22	1.412 (4)	C25—C24	1.370 (5)
C27—C27^ii	1.420 (6)	C20—C21	1.340 (5)
C11—C12—C13	121.6 (3)	N1—C1—C6	121.4 (3)
C5—C4—C3	120.7 (3)	C2—C1—C6	118.9 (3)
C1—N1—C13	119.8 (3)	C10—C9—C8	121.3 (3)
C24—C23—C22	120.7 (3)	C7—C8—C9	123.8 (3)
O4—N3—O3	122.7 (3)	C7—C8—C13	117.3 (3)
O4—N3—C14	118.8 (3)	C9—C8—C13	118.9 (3)
O3—N3—C14	118.4 (3)	C19—C18—C17	118.9 (3)
C29—N2—C30^i	119.7 (3)	C7—C6—C5	123.7 (3)
C4—C5—C6	121.1 (3)	C7—C6—C1	118.1 (3)
N1—C13—C12	119.9 (3)	C5—C6—C1	118.2 (3)
N1—C13—C8	122.2 (3)	C3—C2—C1	120.6 (3)
C12—C13—C8	117.9 (3)	C12—C11—C10	120.4 (3)
C22—C27—C27^ii	120.2 (4)	C19—C14—C15	123.2 (3)
C22—C27—C26	120.0 (3)	C19—C14—N3	117.0 (3)
C27^ii—C27—C26	119.7 (4)	C15—C14—N3	119.8 (3)
C6—C7—C8	121.2 (3)	C2—C3—C4	120.6 (3)
N2^i—C30—C29	119.9 (3)	O2—C15—C16	124.6 (3)
N2^i—C30—C31	117.3 (3)	O2—C15—C14	117.3 (3)
C29—C30—C31	122.8 (3)	C16—C15—C14	118.1 (3)
N2—C29—C30	120.5 (3)	C25—C26—C27	118.3 (3)
N2—C29—C28	117.6 (3)	C25—C26—C20^ii	123.3 (3)
C30—C29—C28	121.9 (3)	C27—C26—C20^ii	118.3 (3)
C23—C22—C27	119.0 (3)	C16—C17—C18	122.6 (3)
C23—C22—C21	122.3 (3)	C24—C25—C26	121.3 (3)
C27—C22—C21	118.6 (3)	C9—C10—C11	119.9 (3)
O1—C19—C18	125.7 (3)	C15—C16—C17	119.2 (3)
O1—C19—C14	116.3 (3)	C21—C20—C26^ii	121.8 (3)
C18—C19—C14	118.0 (3)	C20—C21—C22	121.3 (3)
N1—C1—C2	119.7 (3)	C25—C24—C23	120.6 (3)

Symmetry codes: (i) −x, −y, −z+2; (ii) −x+1, −y, −z+2.

(19NTES-TMP-PYR-4DMAP)

Crystal data

C50H52N8O8	Z = 1
Mr = 892.99	F(000) = 472
Triclinic, P1	Dx = 1.324 Mg m^−3
a = 7.7634 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9486 (14) Å	Cell parameters from 9566 reflections
c = 16.368 (3) Å	θ = 3.1–27.7°
α = 83.021 (6)°	µ = 0.09 mm^−1
β = 82.842 (6)°	T = 150 K
γ = 88.111 (6)°	Block, yellow
V = 1119.7 (3) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3585 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.040
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −10→10
Tmin = 0.764, Tmax = 1.000	k = −11→11
11576 measured reflections	l = −21→21
5114 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.063	w = 1/[σ^2(Fo^2) + (0.0718P)^2 + 1.6202P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.206	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.50 e Å^−3
5114 reflections	Δρmin = −0.34 e Å^−3
305 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.005 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O4	0.9664 (3)	0.6218 (2)	0.35641 (14)	0.0311 (5)
H4	1.040209	0.668948	0.373751	0.047*
N1	0.7532 (3)	0.4694 (3)	0.27859 (14)	0.0226 (5)
O3	0.8895 (3)	0.2465 (2)	0.18933 (14)	0.0322 (5)
H3	0.941730	0.197163	0.154721	0.048*
C14	1.4707 (3)	0.9246 (3)	0.00892 (17)	0.0227 (6)
C5	1.2219 (4)	0.4850 (3)	0.30280 (18)	0.0252 (6)
H5	1.296170	0.537553	0.328934	0.030*
C1	0.9398 (3)	0.4334 (3)	0.27193 (16)	0.0212 (5)
O1	0.6651 (3)	0.4366 (3)	0.34456 (14)	0.0428 (6)
O2	0.6945 (3)	0.5323 (3)	0.21745 (16)	0.0487 (7)
C3	1.1821 (4)	0.2929 (3)	0.21445 (18)	0.0276 (6)
H3A	1.229767	0.219142	0.182549	0.033*
C8	1.4317 (4)	0.8451 (3)	−0.05669 (19)	0.0282 (6)
C2	1.0039 (4)	0.3222 (3)	0.22311 (17)	0.0236 (6)
C12	1.4501 (4)	0.8543 (3)	0.09164 (18)	0.0272 (6)
C6	1.0438 (4)	0.5165 (3)	0.31258 (16)	0.0226 (6)
C4	1.2877 (4)	0.3754 (3)	0.25409 (18)	0.0276 (6)
H4A	1.406764	0.356307	0.247698	0.033*
C7	1.4527 (4)	0.9207 (4)	−0.13959 (19)	0.0331 (7)
H7	1.426328	0.870442	−0.182823	0.040*
C13	1.4904 (4)	0.9375 (4)	0.15622 (19)	0.0333 (7)
H13	1.476793	0.892173	0.210804	0.040*
C11	1.3931 (4)	0.7051 (4)	0.1068 (2)	0.0353 (7)
H11	1.379326	0.657217	0.160878	0.042*
C9	1.3749 (4)	0.6968 (4)	−0.0375 (2)	0.0373 (8)
H9	1.348593	0.643525	−0.079647	0.045*
C10	1.3574 (4)	0.6287 (4)	0.0434 (2)	0.0409 (8)
H10	1.320935	0.529597	0.054945	0.049*
N2	0.0153 (3)	0.0765 (3)	0.06661 (14)	0.0235 (5)
C17	−0.0266 (3)	−0.0691 (3)	0.07848 (17)	0.0224 (6)
C16	0.0430 (3)	0.1466 (3)	−0.01085 (17)	0.0228 (6)
C18	−0.0504 (4)	−0.1448 (3)	0.16599 (18)	0.0324 (7)
H18A	0.039526	−0.219640	0.173301	0.049*
H18B	−0.161592	−0.191865	0.177063	0.049*
H18C	−0.044489	−0.071213	0.203585	0.049*
C15	0.0957 (4)	0.3082 (3)	−0.0211 (2)	0.0319 (7)
H15A	0.067804	0.348953	0.030636	0.048*
H15B	0.034574	0.364627	−0.062572	0.048*
H15C	0.218437	0.314497	−0.037994	0.048*
N3	0.1487 (3)	0.8039 (3)	0.41817 (17)	0.0341 (6)
N4	0.3087 (3)	1.1481 (3)	0.54141 (15)	0.0284 (5)
C23	0.2588 (3)	1.0356 (3)	0.50138 (17)	0.0243 (6)
C22	0.2488 (4)	0.8856 (3)	0.53792 (19)	0.0299 (6)
H22	0.279286	0.859630	0.591049	0.036*
C25	0.3480 (4)	1.1189 (4)	0.62660 (19)	0.0344 (7)
H25A	0.251559	1.070105	0.660726	0.052*
H25B	0.368849	1.212455	0.646552	0.052*
H25C	0.449529	1.055056	0.628717	0.052*
C21	0.2136 (4)	1.0639 (3)	0.42001 (18)	0.0295 (6)
H21	0.220125	1.160708	0.391909	0.035*
C20	0.1939 (4)	0.7771 (3)	0.4950 (2)	0.0321 (7)
H20	0.187586	0.678755	0.521010	0.039*
C24	0.3248 (4)	1.3006 (3)	0.4999 (2)	0.0339 (7)
H24A	0.403275	1.300921	0.449724	0.051*
H24B	0.368797	1.363717	0.535728	0.051*
H24C	0.212958	1.338187	0.486920	0.051*
C19	0.1598 (4)	0.9472 (4)	0.38265 (19)	0.0327 (7)
H19	0.129024	0.968814	0.329300	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0274 (10)	0.0323 (11)	0.0383 (12)	−0.0005 (9)	−0.0070 (9)	−0.0195 (9)
N1	0.0213 (11)	0.0234 (11)	0.0240 (12)	−0.0024 (9)	−0.0048 (9)	−0.0045 (9)
O3	0.0270 (10)	0.0391 (12)	0.0352 (12)	−0.0027 (9)	−0.0045 (9)	−0.0223 (9)
C14	0.0173 (12)	0.0237 (13)	0.0274 (14)	0.0048 (10)	−0.0052 (10)	−0.0037 (11)
C5	0.0236 (13)	0.0263 (14)	0.0277 (14)	−0.0053 (11)	−0.0084 (11)	−0.0039 (11)
C1	0.0212 (13)	0.0240 (13)	0.0180 (12)	−0.0002 (10)	−0.0032 (10)	−0.0011 (10)
O1	0.0269 (11)	0.0687 (17)	0.0296 (12)	−0.0018 (11)	0.0029 (9)	0.0001 (11)
O2	0.0301 (12)	0.0611 (17)	0.0493 (15)	0.0009 (11)	−0.0112 (11)	0.0219 (12)
C3	0.0271 (14)	0.0289 (15)	0.0274 (14)	0.0022 (11)	−0.0009 (12)	−0.0092 (11)
C8	0.0208 (13)	0.0265 (14)	0.0384 (16)	0.0053 (11)	−0.0055 (12)	−0.0076 (12)
C2	0.0261 (14)	0.0239 (13)	0.0210 (13)	−0.0027 (11)	−0.0013 (11)	−0.0041 (10)
C12	0.0197 (13)	0.0298 (15)	0.0302 (15)	0.0046 (11)	−0.0027 (11)	0.0023 (12)
C6	0.0271 (14)	0.0227 (13)	0.0183 (12)	−0.0019 (11)	−0.0038 (11)	−0.0024 (10)
C4	0.0202 (13)	0.0330 (15)	0.0300 (15)	−0.0002 (11)	−0.0042 (11)	−0.0036 (12)
C7	0.0298 (15)	0.0444 (18)	0.0285 (15)	0.0077 (13)	−0.0087 (12)	−0.0145 (13)
C13	0.0271 (15)	0.0465 (19)	0.0253 (15)	0.0032 (13)	−0.0046 (12)	−0.0004 (13)
C11	0.0250 (15)	0.0315 (16)	0.0454 (18)	0.0015 (12)	−0.0036 (13)	0.0104 (14)
C9	0.0306 (16)	0.0285 (16)	0.057 (2)	0.0034 (13)	−0.0131 (15)	−0.0143 (15)
C10	0.0317 (16)	0.0219 (15)	0.069 (2)	−0.0010 (12)	−0.0129 (16)	0.0011 (15)
N2	0.0251 (12)	0.0236 (12)	0.0223 (11)	0.0001 (9)	−0.0016 (9)	−0.0066 (9)
C17	0.0222 (13)	0.0226 (13)	0.0225 (13)	0.0015 (10)	−0.0016 (10)	−0.0045 (10)
C16	0.0208 (13)	0.0209 (13)	0.0265 (14)	0.0017 (10)	−0.0008 (11)	−0.0047 (10)
C18	0.0397 (17)	0.0324 (16)	0.0235 (14)	0.0017 (13)	−0.0020 (13)	0.0005 (12)
C15	0.0342 (16)	0.0216 (14)	0.0394 (17)	−0.0037 (12)	0.0007 (13)	−0.0056 (12)
N3	0.0304 (13)	0.0335 (14)	0.0421 (15)	−0.0009 (11)	−0.0074 (12)	−0.0163 (12)
N4	0.0318 (13)	0.0305 (13)	0.0251 (12)	−0.0024 (10)	−0.0061 (10)	−0.0089 (10)
C23	0.0208 (13)	0.0290 (15)	0.0238 (14)	0.0004 (11)	−0.0007 (11)	−0.0084 (11)
C22	0.0292 (15)	0.0323 (16)	0.0296 (15)	0.0016 (12)	−0.0069 (12)	−0.0061 (12)
C25	0.0387 (17)	0.0416 (18)	0.0265 (15)	0.0032 (14)	−0.0099 (13)	−0.0133 (13)
C21	0.0296 (15)	0.0310 (15)	0.0287 (15)	−0.0004 (12)	−0.0051 (12)	−0.0056 (12)
C20	0.0303 (15)	0.0281 (15)	0.0389 (17)	0.0007 (12)	−0.0051 (13)	−0.0075 (13)
C24	0.0387 (17)	0.0295 (16)	0.0346 (16)	−0.0077 (13)	0.0002 (14)	−0.0111 (13)
C19	0.0320 (16)	0.0403 (18)	0.0292 (15)	0.0021 (13)	−0.0105 (13)	−0.0113 (13)

Geometric parameters (Å, º)

O4—C6	1.336 (3)	C7—C13^i	1.342 (5)
N1—O1	1.213 (3)	C11—C10	1.371 (5)
N1—O2	1.219 (3)	C9—C10	1.381 (5)
N1—C1	1.467 (3)	N2—C17	1.338 (4)
O3—C2	1.344 (3)	N2—C16	1.340 (4)
C14—C12	1.414 (4)	C17—C16^ii	1.396 (4)
C14—C14^i	1.423 (5)	C17—C18	1.500 (4)
C14—C8	1.426 (4)	C16—C15	1.500 (4)
C5—C4	1.383 (4)	N3—C20	1.340 (4)
C5—C6	1.395 (4)	N3—C19	1.343 (4)
C1—C2	1.392 (4)	N4—C23	1.357 (4)
C1—C6	1.393 (4)	N4—C24	1.451 (4)
C3—C4	1.388 (4)	N4—C25	1.455 (4)
C3—C2	1.393 (4)	C23—C22	1.402 (4)
C8—C9	1.399 (4)	C23—C21	1.411 (4)
C8—C7	1.433 (4)	C22—C20	1.372 (4)
C12—C11	1.404 (4)	C21—C19	1.374 (4)
C12—C13	1.434 (4)
O1—N1—O2	123.1 (2)	C13^i—C7—C8	121.5 (3)
O1—N1—C1	118.7 (2)	C7^i—C13—C12	121.4 (3)
O2—N1—C1	118.1 (2)	C10—C11—C12	121.1 (3)
C12—C14—C14^i	120.0 (3)	C10—C9—C8	120.6 (3)
C12—C14—C8	120.2 (3)	C11—C10—C9	121.0 (3)
C14^i—C14—C8	119.8 (3)	C17—N2—C16	119.3 (2)
C4—C5—C6	119.8 (3)	N2—C17—C16^ii	120.3 (2)
C2—C1—C6	123.7 (2)	N2—C17—C18	117.6 (2)
C2—C1—N1	118.3 (2)	C16^ii—C17—C18	122.1 (3)
C6—C1—N1	117.9 (2)	N2—C16—C17^ii	120.4 (2)
C4—C3—C2	119.1 (3)	N2—C16—C15	117.3 (2)
C9—C8—C14	118.7 (3)	C17^ii—C16—C15	122.3 (3)
C9—C8—C7	122.8 (3)	C20—N3—C19	116.2 (3)
C14—C8—C7	118.5 (3)	C23—N4—C24	120.6 (2)
O3—C2—C1	118.0 (2)	C23—N4—C25	121.0 (3)
O3—C2—C3	124.0 (2)	C24—N4—C25	118.4 (2)
C1—C2—C3	117.9 (3)	N4—C23—C22	122.4 (3)
C11—C12—C14	118.4 (3)	N4—C23—C21	121.4 (3)
C11—C12—C13	122.8 (3)	C22—C23—C21	116.1 (3)
C14—C12—C13	118.8 (3)	C20—C22—C23	119.8 (3)
O4—C6—C1	117.8 (2)	C19—C21—C23	119.4 (3)
O4—C6—C5	125.1 (2)	N3—C20—C22	124.2 (3)
C1—C6—C5	117.2 (2)	N3—C19—C21	124.2 (3)
C5—C4—C3	122.3 (3)

Symmetry codes: (i) −x+3, −y+2, −z; (ii) −x, −y, −z.

(20NRES-TMP-22BP-DPE-I)

Crystal data

C42H42N8O8	Z = 1
Mr = 786.83	F(000) = 414
Triclinic, P1	Dx = 1.323 Mg m^−3
a = 7.5543 (17) Å	Mo Kα radiation, λ = 0.71075 Å
b = 8.914 (2) Å	Cell parameters from 7266 reflections
c = 14.713 (3) Å	θ = 3.0–27.6°
α = 85.797 (7)°	µ = 0.09 mm^−1
β = 88.497 (6)°	T = 150 K
γ = 89.487 (6)°	Block, yellow
V = 987.7 (4) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2412 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.043
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.772, Tmax = 1.000	k = −11→11
10148 measured reflections	l = −19→19
4515 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.193	w = 1/[σ^2(Fo^2) + (0.0952P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.027
4515 reflections	Δρmax = 0.26 e Å^−3
264 parameters	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O2	0.1600 (2)	0.37317 (19)	0.11278 (11)	0.0614 (5)
H2	0.254062	0.331732	0.100473	0.092*
O1	−0.0942 (2)	0.7499 (2)	0.27973 (12)	0.0677 (6)
H1	−0.071858	0.814464	0.314610	0.102*
N4	−0.1307 (3)	0.5315 (2)	0.16364 (13)	0.0453 (5)
N1	−0.0334 (3)	0.9191 (2)	0.42699 (13)	0.0489 (5)
O3	−0.1949 (3)	0.6154 (2)	0.10577 (15)	0.0842 (7)
N2	0.4546 (3)	0.2088 (2)	0.07952 (14)	0.0559 (6)
O4	−0.2040 (3)	0.4208 (3)	0.19732 (16)	0.0852 (7)
N3	0.5702 (3)	0.1811 (2)	0.53041 (14)	0.0585 (6)
C2	0.0444 (3)	0.5674 (2)	0.19581 (13)	0.0381 (5)
C3	0.1897 (3)	0.4842 (2)	0.16750 (14)	0.0426 (6)
C1	0.0578 (3)	0.6813 (3)	0.25424 (15)	0.0477 (6)
C21	0.5280 (3)	0.0723 (3)	0.47670 (15)	0.0452 (6)
C15	0.7913 (3)	0.0807 (3)	0.05792 (16)	0.0510 (6)
C9	0.0225 (3)	1.0620 (3)	0.41331 (16)	0.0469 (6)
C8	−0.0562 (3)	0.8566 (2)	0.51181 (17)	0.0487 (6)
C13	0.6599 (4)	0.0086 (3)	0.10983 (17)	0.0564 (7)
H13	0.681623	−0.085788	0.138799	0.068*
C4	0.3550 (3)	0.5233 (3)	0.19673 (17)	0.0543 (7)
H4	0.455705	0.471716	0.178294	0.065*
C6	0.2240 (4)	0.7181 (3)	0.28279 (18)	0.0607 (7)
H6	0.237432	0.795123	0.321363	0.073*
C5	0.3692 (4)	0.6389 (3)	0.25317 (18)	0.0605 (7)
H5	0.480853	0.664467	0.271979	0.073*
C20	0.5357 (4)	0.0945 (3)	0.38258 (17)	0.0573 (7)
H20	0.507225	0.016978	0.346712	0.069*
C11	0.4966 (4)	0.0749 (3)	0.11920 (17)	0.0588 (7)
H11	0.410637	0.023422	0.155247	0.071*
C16	0.9742 (4)	0.0151 (3)	0.04730 (18)	0.0656 (8)
H16A	1.058883	0.084016	0.069508	0.079*
H16B	0.981071	−0.078259	0.085312	0.079*
C14	0.7471 (4)	0.2181 (3)	0.0162 (2)	0.0692 (8)
H14	0.830182	0.271278	−0.020806	0.083*
C18	0.6284 (4)	0.3442 (3)	0.3971 (2)	0.0672 (8)
H18	0.662858	0.438368	0.371579	0.081*
C17	0.6191 (4)	0.3141 (3)	0.4892 (2)	0.0669 (8)
H17	0.648378	0.390453	0.525743	0.080*
C12	0.5805 (4)	0.2775 (3)	0.0290 (2)	0.0694 (8)
H12	0.555202	0.371434	0.000301	0.083*
C19	0.5855 (4)	0.2314 (3)	0.34296 (19)	0.0687 (8)
H19	0.590348	0.248188	0.279808	0.082*
C10	0.0461 (4)	1.1256 (3)	0.31701 (18)	0.0723 (8)
H10A	−0.011855	1.062217	0.277117	0.108*
H10B	0.170090	1.130590	0.301141	0.108*
H10C	−0.004745	1.224772	0.310887	0.108*
C7	−0.1188 (4)	0.6964 (3)	0.5224 (2)	0.0729 (9)
H7A	−0.137476	0.661082	0.463346	0.109*
H7B	−0.227874	0.691294	0.557449	0.109*
H7C	−0.031006	0.634569	0.553213	0.109*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0458 (11)	0.0696 (12)	0.0730 (11)	0.0149 (9)	−0.0031 (9)	−0.0357 (10)
O1	0.0514 (11)	0.0846 (13)	0.0733 (12)	0.0225 (10)	−0.0087 (9)	−0.0477 (10)
N4	0.0392 (11)	0.0526 (12)	0.0452 (11)	0.0083 (10)	0.0014 (9)	−0.0125 (10)
N1	0.0483 (13)	0.0491 (12)	0.0513 (12)	0.0103 (10)	−0.0022 (9)	−0.0185 (10)
O3	0.0740 (15)	0.0890 (15)	0.0897 (15)	0.0024 (12)	−0.0422 (12)	0.0059 (12)
N2	0.0488 (13)	0.0610 (14)	0.0595 (13)	0.0208 (11)	0.0012 (10)	−0.0184 (11)
O4	0.0523 (13)	0.0928 (16)	0.1066 (17)	−0.0226 (12)	0.0023 (11)	0.0202 (13)
N3	0.0666 (16)	0.0538 (13)	0.0559 (12)	−0.0069 (11)	−0.0079 (11)	−0.0061 (11)
C2	0.0336 (12)	0.0453 (12)	0.0362 (11)	0.0025 (10)	−0.0026 (9)	−0.0081 (10)
C3	0.0399 (14)	0.0485 (14)	0.0402 (12)	0.0085 (11)	−0.0008 (10)	−0.0100 (10)
C1	0.0434 (14)	0.0547 (14)	0.0467 (13)	0.0132 (11)	−0.0030 (11)	−0.0172 (11)
C21	0.0365 (13)	0.0516 (13)	0.0482 (14)	0.0008 (11)	−0.0091 (10)	−0.0053 (11)
C15	0.0499 (15)	0.0535 (15)	0.0502 (13)	0.0183 (12)	0.0031 (12)	−0.0114 (12)
C9	0.0432 (14)	0.0467 (14)	0.0516 (14)	0.0127 (11)	−0.0002 (11)	−0.0107 (11)
C8	0.0462 (14)	0.0404 (13)	0.0604 (16)	0.0098 (11)	0.0004 (12)	−0.0124 (11)
C13	0.0593 (17)	0.0531 (15)	0.0560 (15)	0.0127 (13)	0.0061 (13)	−0.0020 (12)
C4	0.0371 (14)	0.0656 (16)	0.0613 (15)	0.0131 (12)	−0.0014 (12)	−0.0141 (13)
C6	0.0541 (17)	0.0659 (17)	0.0662 (17)	0.0083 (14)	−0.0146 (13)	−0.0286 (14)
C5	0.0409 (15)	0.0739 (18)	0.0695 (17)	0.0059 (13)	−0.0138 (13)	−0.0201 (14)
C20	0.0633 (18)	0.0596 (16)	0.0495 (15)	−0.0047 (14)	−0.0046 (13)	−0.0053 (13)
C11	0.0525 (17)	0.0653 (18)	0.0586 (16)	0.0085 (14)	0.0095 (13)	−0.0085 (13)
C16	0.0544 (17)	0.0783 (19)	0.0648 (16)	0.0240 (14)	0.0031 (13)	−0.0141 (14)
C14	0.0643 (19)	0.0590 (17)	0.0810 (19)	0.0185 (14)	0.0252 (15)	0.0062 (15)
C18	0.068 (2)	0.0596 (17)	0.0722 (19)	−0.0113 (15)	−0.0070 (15)	0.0101 (15)
C17	0.073 (2)	0.0529 (17)	0.076 (2)	−0.0096 (14)	−0.0076 (15)	−0.0070 (15)
C12	0.073 (2)	0.0518 (16)	0.0810 (19)	0.0287 (14)	0.0165 (16)	0.0016 (14)
C19	0.081 (2)	0.0708 (19)	0.0530 (16)	−0.0114 (16)	−0.0036 (15)	0.0069 (15)
C10	0.075 (2)	0.081 (2)	0.0594 (17)	0.0107 (17)	0.0011 (15)	0.0004 (15)
C7	0.071 (2)	0.0485 (16)	0.100 (2)	−0.0003 (14)	0.0038 (17)	−0.0173 (15)

Geometric parameters (Å, º)

O2—C3	1.344 (3)	C13—H13	0.9300
O2—H2	0.8200	C4—C5	1.377 (4)
O1—C1	1.354 (3)	C4—H4	0.9300
O1—H1	0.8200	C6—C5	1.378 (4)
N4—O3	1.201 (3)	C6—H6	0.9300
N4—O4	1.204 (3)	C5—H5	0.9300
N4—C2	1.462 (3)	C20—C19	1.365 (4)
N1—C8	1.336 (3)	C20—H20	0.9300
N1—C9	1.345 (3)	C11—H11	0.9300
N2—C12	1.319 (3)	C16—C16^iii	1.479 (5)
N2—C11	1.330 (3)	C16—H16A	0.9700
N3—C17	1.342 (3)	C16—H16B	0.9700
N3—C21	1.340 (3)	C14—C12	1.374 (4)
C2—C1	1.383 (3)	C14—H14	0.9300
C2—C3	1.391 (3)	C18—C17	1.362 (4)
C3—C4	1.387 (3)	C18—C19	1.374 (4)
C1—C6	1.384 (3)	C18—H18	0.9300
C21—C20	1.384 (3)	C17—H17	0.9300
C21—C21^i	1.475 (5)	C12—H12	0.9300
C15—C13	1.372 (4)	C19—H19	0.9300
C15—C14	1.371 (3)	C10—H10A	0.9600
C15—C16	1.504 (3)	C10—H10B	0.9600
C9—C8^ii	1.393 (3)	C10—H10C	0.9600
C9—C10	1.494 (3)	C7—H7A	0.9600
C8—C7	1.504 (3)	C7—H7B	0.9600
C13—C11	1.371 (4)	C7—H7C	0.9600
C3—O2—H2	109.5	C6—C5—H5	118.8
C1—O1—H1	109.5	C19—C20—C21	119.3 (2)
O3—N4—O4	123.4 (2)	C19—C20—H20	120.3
O3—N4—C2	118.1 (2)	C21—C20—H20	120.3
O4—N4—C2	118.5 (2)	N2—C11—C13	123.5 (2)
C8—N1—C9	120.0 (2)	N2—C11—H11	118.2
C12—N2—C11	116.1 (2)	C13—C11—H11	118.2
C17—N3—C21	117.2 (2)	C16^iii—C16—C15	114.4 (3)
C1—C2—C3	122.9 (2)	C16^iii—C16—H16A	108.7
C1—C2—N4	118.47 (18)	C15—C16—H16A	108.7
C3—C2—N4	118.62 (18)	C16^iii—C16—H16B	108.7
O2—C3—C4	124.8 (2)	C15—C16—H16B	108.7
O2—C3—C2	117.7 (2)	H16A—C16—H16B	107.6
C4—C3—C2	117.5 (2)	C15—C14—C12	120.3 (3)
O1—C1—C6	124.2 (2)	C15—C14—H14	119.9
O1—C1—C2	117.3 (2)	C12—C14—H14	119.9
C6—C1—C2	118.5 (2)	C17—C18—C19	118.0 (3)
N3—C21—C20	121.9 (2)	C17—C18—H18	121.0
N3—C21—C21^i	116.4 (2)	C19—C18—H18	121.0
C20—C21—C21^i	121.7 (3)	N3—C17—C18	124.1 (3)
C13—C15—C14	116.1 (2)	N3—C17—H17	117.9
C13—C15—C16	122.6 (2)	C18—C17—H17	117.9
C14—C15—C16	121.3 (2)	N2—C12—C14	123.7 (2)
N1—C9—C8^ii	119.4 (2)	N2—C12—H12	118.1
N1—C9—C10	117.6 (2)	C14—C12—H12	118.1
C8^ii—C9—C10	123.1 (2)	C20—C19—C18	119.5 (3)
N1—C8—C9^ii	120.7 (2)	C20—C19—H19	120.3
N1—C8—C7	117.3 (2)	C18—C19—H19	120.3
C9^ii—C8—C7	122.0 (2)	C9—C10—H10A	109.5
C15—C13—C11	120.3 (2)	C9—C10—H10B	109.5
C15—C13—H13	119.8	H10A—C10—H10B	109.5
C11—C13—H13	119.8	C9—C10—H10C	109.5
C5—C4—C3	119.6 (2)	H10A—C10—H10C	109.5
C5—C4—H4	120.2	H10B—C10—H10C	109.5
C3—C4—H4	120.2	C8—C7—H7A	109.5
C5—C6—C1	119.0 (2)	C8—C7—H7B	109.5
C5—C6—H6	120.5	H7A—C7—H7B	109.5
C1—C6—H6	120.5	C8—C7—H7C	109.5
C4—C5—C6	122.4 (3)	H7A—C7—H7C	109.5
C4—C5—H5	118.8	H7B—C7—H7C	109.5

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+2, −z+1; (iii) −x+2, −y, −z.

(21NRES-TMP-22BP-DPE-II)

Crystal data

C42H40N8O8	Z = 1
Mr = 784.82	F(000) = 412
Triclinic, P1	Dx = 1.310 Mg m^−3
a = 7.504 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.428 (4) Å	Cell parameters from 4722 reflections
c = 14.102 (6) Å	θ = 3.0–28.1°
α = 94.052 (8)°	µ = 0.09 mm^−1
β = 91.192 (7)°	T = 150 K
γ = 90.498 (8)°	Prism, colorless
V = 995.0 (7) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	1160 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.147
profile data from ω–scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan	h = −8→8
Tmin = 0.531, Tmax = 1.000	k = −11→11
7618 measured reflections	l = −16→16
3479 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.093	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.260	w = 1/[σ^2(Fo^2) + (0.0989P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max < 0.001
3479 reflections	Δρmax = 0.25 e Å^−3
268 parameters	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9198 (10)	0.6853 (7)	0.2538 (4)	0.0561 (18)
C34	0.4327 (12)	0.7608 (12)	0.8657 (6)	0.091 (3)
H34	0.433257	0.735672	0.800709	0.109*
O1	0.8452 (6)	0.3620 (5)	0.3756 (3)	0.0678 (14)
H1	0.752205	0.322579	0.389173	0.102*
N2	0.5427 (7)	0.2065 (6)	0.4074 (4)	0.0587 (16)
C2	0.9455 (9)	0.5629 (7)	0.3021 (4)	0.0492 (17)
C4	0.6329 (9)	0.5264 (7)	0.3149 (4)	0.0550 (18)
H4	0.536371	0.474360	0.334815	0.066*
N1	0.9845 (7)	0.9181 (6)	0.0769 (4)	0.0533 (14)
C3	0.8069 (9)	0.4818 (7)	0.3323 (4)	0.0477 (17)
N3	1.1325 (8)	0.5226 (6)	0.3236 (5)	0.0578 (16)
C12	0.2237 (9)	0.0592 (7)	0.4484 (4)	0.0527 (18)
C6	0.7450 (10)	0.7281 (7)	0.2348 (4)	0.066 (2)
H6	0.723069	0.807440	0.200885	0.079*
C16	0.9573 (8)	0.8590 (7)	−0.0114 (5)	0.0495 (17)
C5	0.6054 (9)	0.6487 (7)	0.2679 (5)	0.0586 (19)
H5	0.489182	0.678780	0.258087	0.070*
O2	1.0670 (6)	0.7546 (4)	0.2244 (3)	0.0682 (14)
H2	1.035990	0.822180	0.194688	0.102*
O3	1.2044 (7)	0.5777 (7)	0.3936 (4)	0.102 (2)
O4	1.2023 (7)	0.4401 (6)	0.2677 (5)	0.108 (2)
C15	1.0266 (8)	1.0586 (7)	0.0898 (4)	0.0487 (17)
C13	0.0639 (9)	−0.0232 (8)	0.4712 (5)	0.0585 (19)
C14	1.0544 (11)	1.1204 (7)	0.1909 (5)	0.079 (2)
H14A	1.008927	1.055124	0.233928	0.118*
H14B	0.992530	1.208912	0.199244	0.118*
H14C	1.179406	1.136333	0.203608	0.118*
C11	0.2596 (9)	0.1973 (7)	0.4844 (5)	0.063 (2)
H11	0.177827	0.244517	0.523584	0.076*
C8	0.3565 (9)	−0.0024 (7)	0.3920 (4)	0.0582 (19)
H8	0.342176	−0.095551	0.366492	0.070*
C9	0.5091 (9)	0.0728 (8)	0.3733 (5)	0.064 (2)
H9	0.593553	0.027671	0.334629	0.077*
C10	0.4171 (10)	0.2664 (7)	0.4624 (5)	0.069 (2)
H10	0.435684	0.359371	0.487504	0.082*
C17	0.9080 (9)	0.7029 (7)	−0.0208 (5)	0.071 (2)
H17A	0.969445	0.656926	−0.073322	0.106*
H17B	0.781656	0.692411	−0.031667	0.106*
H17C	0.941381	0.660074	0.036654	0.106*
C21	0.4743 (8)	0.9252 (6)	0.9863 (5)	0.0560 (18)
C22	0.4236 (9)	0.8324 (8)	1.0521 (5)	0.063 (2)
H22	0.422148	0.861696	1.116423	0.076*
C18	0.3800 (10)	0.6546 (9)	0.9252 (7)	0.087 (3)
H18	0.350549	0.562795	0.901132	0.104*
C23	0.3746 (10)	0.6943 (8)	1.0208 (7)	0.079 (2)
H23	0.338762	0.629798	1.063733	0.095*
N19	0.4764 (9)	0.8795 (8)	0.8906 (4)	0.078 (2)
H13	0.078 (9)	−0.126 (7)	0.453 (4)	0.09 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.043 (5)	0.067 (5)	0.058 (4)	−0.012 (4)	0.003 (3)	0.010 (4)
C34	0.087 (7)	0.118 (8)	0.070 (6)	−0.006 (6)	0.004 (5)	0.021 (7)
O1	0.044 (3)	0.074 (3)	0.088 (3)	−0.009 (2)	0.009 (2)	0.030 (3)
N2	0.056 (4)	0.049 (4)	0.072 (4)	−0.007 (3)	0.009 (3)	0.012 (3)
C2	0.036 (5)	0.055 (4)	0.059 (4)	−0.003 (3)	0.006 (3)	0.019 (4)
C4	0.032 (5)	0.075 (5)	0.059 (4)	0.000 (4)	0.010 (3)	0.017 (4)
N1	0.047 (4)	0.050 (4)	0.063 (4)	−0.004 (3)	0.004 (3)	0.004 (3)
C3	0.043 (5)	0.048 (4)	0.053 (4)	−0.005 (3)	0.003 (3)	0.008 (3)
N3	0.044 (5)	0.063 (4)	0.067 (5)	−0.010 (3)	0.005 (3)	0.005 (3)
C12	0.053 (5)	0.055 (4)	0.051 (4)	−0.013 (4)	0.005 (3)	0.005 (3)
C6	0.063 (6)	0.072 (5)	0.064 (5)	−0.006 (4)	0.002 (4)	0.022 (4)
C16	0.030 (4)	0.056 (5)	0.063 (5)	0.002 (3)	0.000 (3)	0.007 (4)
C5	0.035 (5)	0.071 (5)	0.072 (5)	0.008 (4)	0.009 (3)	0.015 (4)
O2	0.050 (3)	0.074 (3)	0.084 (3)	−0.013 (2)	0.000 (2)	0.032 (3)
O3	0.049 (4)	0.172 (6)	0.083 (4)	0.004 (4)	−0.012 (3)	−0.013 (4)
O4	0.055 (4)	0.108 (5)	0.152 (5)	0.007 (3)	0.004 (3)	−0.049 (4)
C15	0.036 (4)	0.058 (5)	0.051 (5)	−0.004 (3)	0.001 (3)	−0.003 (4)
C13	0.058 (6)	0.049 (5)	0.069 (5)	−0.004 (4)	0.008 (3)	0.012 (4)
C14	0.092 (7)	0.074 (5)	0.072 (5)	−0.011 (4)	0.011 (4)	0.010 (4)
C11	0.051 (5)	0.060 (5)	0.079 (5)	−0.014 (4)	0.022 (4)	−0.001 (4)
C8	0.052 (5)	0.056 (4)	0.067 (5)	−0.005 (4)	0.005 (4)	0.006 (4)
C9	0.040 (5)	0.074 (6)	0.081 (5)	0.006 (4)	0.015 (4)	0.013 (4)
C10	0.073 (6)	0.061 (5)	0.071 (5)	−0.017 (4)	0.011 (4)	−0.006 (4)
C17	0.065 (6)	0.057 (5)	0.090 (5)	−0.004 (4)	0.001 (4)	0.007 (4)
C21	0.043 (5)	0.069 (5)	0.055 (5)	0.013 (4)	−0.002 (3)	−0.002 (4)
C22	0.053 (5)	0.071 (6)	0.067 (5)	0.012 (4)	−0.004 (4)	0.017 (4)
C18	0.077 (7)	0.088 (6)	0.094 (7)	0.004 (5)	0.007 (5)	−0.007 (6)
C23	0.082 (7)	0.054 (6)	0.104 (7)	0.012 (4)	0.011 (5)	0.021 (5)
N19	0.069 (5)	0.100 (6)	0.061 (5)	0.001 (4)	−0.006 (3)	−0.015 (4)

Geometric parameters (Å, º)

C1—O2	1.365 (7)	C12—C11	1.386 (8)
C1—C2	1.394 (8)	C12—C8	1.394 (8)
C1—C6	1.401 (9)	C12—C13	1.476 (8)
C34—N19	1.190 (9)	C6—C5	1.390 (8)
C34—C18	1.410 (10)	C16—C15^i	1.401 (8)
O1—C3	1.352 (7)	C16—C17	1.511 (8)
N2—C10	1.337 (7)	C15—C14	1.511 (8)
N2—C9	1.338 (7)	C13—C13^ii	1.327 (12)
C2—C3	1.378 (8)	C11—C10	1.395 (8)
C2—N3	1.487 (8)	C8—C9	1.381 (8)
C4—C5	1.385 (8)	C21—C22	1.377 (8)
C4—C3	1.397 (8)	C21—N19	1.388 (8)
N1—C16	1.339 (7)	C21—C21^iii	1.481 (12)
N1—C15	1.358 (7)	C22—C23	1.389 (9)
N3—O3	1.199 (6)	C18—C23	1.375 (10)
N3—O4	1.199 (6)
O2—C1—C2	117.9 (6)	N1—C16—C15^i	120.3 (6)
O2—C1—C6	123.4 (7)	N1—C16—C17	116.7 (6)
C2—C1—C6	118.6 (6)	C15^i—C16—C17	123.0 (6)
N19—C34—C18	126.2 (9)	C4—C5—C6	122.4 (7)
C10—N2—C9	115.6 (5)	N1—C15—C16^i	120.4 (5)
C3—C2—C1	123.0 (7)	N1—C15—C14	117.3 (6)
C3—C2—N3	119.6 (6)	C16^i—C15—C14	122.3 (6)
C1—C2—N3	117.4 (5)	C13^ii—C13—C12	125.3 (9)
C5—C4—C3	119.4 (6)	C12—C11—C10	120.8 (6)
C16—N1—C15	119.3 (5)	C9—C8—C12	121.1 (6)
O1—C3—C2	118.7 (6)	N2—C9—C8	123.9 (6)
O1—C3—C4	123.1 (5)	N2—C10—C11	123.7 (6)
C2—C3—C4	118.2 (6)	C22—C21—N19	119.7 (6)
O3—N3—O4	124.6 (7)	C22—C21—C21^iii	122.2 (8)
O3—N3—C2	118.0 (6)	N19—C21—C21^iii	118.0 (9)
O4—N3—C2	117.3 (6)	C21—C22—C23	118.9 (7)
C11—C12—C8	114.9 (6)	C23—C18—C34	116.3 (8)
C11—C12—C13	124.2 (6)	C18—C23—C22	118.8 (8)
C8—C12—C13	120.9 (6)	C34—N19—C21	119.9 (8)
C5—C6—C1	118.2 (7)

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x, −y, −z+1; (iii) −x+1, −y+2, −z+2.

(22NRES-TMP-22TBP-DPE-I)

Crystal data

C40H40N6O8S2	Z = 1
Mr = 796.90	F(000) = 418
Triclinic, P1	Dx = 1.383 Mg m^−3
a = 7.489 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.107 (3) Å	Cell parameters from 5609 reflections
c = 14.187 (5) Å	θ = 3.0–27.6°
α = 97.784 (7)°	µ = 0.20 mm^−1
β = 93.611 (7)°	T = 150 K
γ = 90.872 (6)°	Block, yellow
V = 956.5 (6) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2146 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.086
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.613, Tmax = 1.000	k = −11→11
8562 measured reflections	l = −18→18
4278 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.089	H-atom parameters constrained
wR(F^2) = 0.265	w = 1/[σ^2(Fo^2) + (0.1067P)^2 + 0.7121P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
4278 reflections	Δρmax = 0.34 e Å^−3
255 parameters	Δρmin = −0.66 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N2	−0.0381 (5)	0.2106 (4)	0.4129 (3)	0.0372 (9)
C1	−0.0119 (6)	0.0695 (5)	0.3811 (4)	0.0413 (12)
H1A	−0.108574	0.013409	0.350304	0.050*
C2	0.1056 (6)	0.2882 (5)	0.4571 (3)	0.0407 (12)
H2A	0.090992	0.387175	0.481222	0.049*
C3	0.1517 (6)	−0.0004 (5)	0.3908 (3)	0.0382 (11)
H3	0.162050	−0.100204	0.367608	0.046*
C4	0.2730 (6)	0.2290 (5)	0.4686 (3)	0.0380 (11)
H4	0.368235	0.287968	0.498460	0.046*
C5	0.2980 (6)	0.0812 (5)	0.4354 (3)	0.0299 (10)
C6	0.4790 (6)	0.0139 (6)	0.4484 (3)	0.0377 (11)
H6A	0.570212	0.080050	0.430787	0.045*
H6B	0.482314	−0.079128	0.406300	0.045*
O1	0.6673 (4)	0.3733 (3)	0.3799 (2)	0.0378 (8)
H1	0.757434	0.325799	0.388906	0.057*
O2	0.4421 (4)	0.7509 (3)	0.2137 (2)	0.0397 (8)
H2	0.466938	0.800814	0.172104	0.060*
O3	0.2909 (4)	0.4448 (4)	0.2642 (3)	0.0568 (11)
O4	0.3285 (5)	0.5975 (4)	0.3924 (2)	0.0547 (10)
N3	0.3833 (5)	0.5318 (4)	0.3206 (3)	0.0306 (9)
C7	0.7054 (6)	0.4825 (5)	0.3294 (3)	0.0283 (10)
C8	0.5662 (5)	0.5663 (4)	0.2967 (3)	0.0267 (9)
C9	0.5917 (6)	0.6803 (5)	0.2428 (3)	0.0305 (10)
C10	0.7633 (6)	0.7174 (5)	0.2232 (3)	0.0366 (11)
H10	0.784185	0.795052	0.188696	0.044*
C11	0.9048 (6)	0.6365 (5)	0.2562 (3)	0.0338 (10)
H11	1.020866	0.662221	0.243788	0.041*
C12	0.8789 (6)	0.5202 (5)	0.3062 (3)	0.0331 (10)
H12	0.975993	0.466075	0.324857	0.040*
S1	0.0354 (2)	0.81487 (17)	−0.11311 (11)	0.0627 (5)
C17	0.1035 (8)	0.6659 (6)	−0.0610 (5)	0.0626 (16)
H17	0.127089	0.574163	−0.094770	0.075*
C18	0.1191 (8)	0.6954 (6)	0.0333 (4)	0.0563 (15)
H18	0.154012	0.625008	0.072094	0.068*
C19	0.0784 (6)	0.8431 (5)	0.0707 (4)	0.0421 (12)
H19	0.084706	0.880748	0.135117	0.051*
C20	0.0275 (7)	0.9234 (6)	−0.0033 (4)	0.0462 (13)
N1	0.5146 (5)	0.9158 (4)	0.0728 (3)	0.0315 (8)
C13	0.4688 (8)	1.1244 (6)	0.1933 (3)	0.0525 (14)
H13A	0.489034	1.047811	0.232812	0.079*
H13B	0.351578	1.163210	0.201886	0.079*
H13C	0.557029	1.202456	0.210801	0.079*
C14	0.4823 (6)	1.0612 (5)	0.0907 (3)	0.0340 (10)
C15	0.5335 (6)	0.8531 (5)	−0.0165 (3)	0.0328 (10)
C16	0.5771 (7)	0.6920 (5)	−0.0320 (4)	0.0463 (13)
H16A	0.561294	0.649638	0.025437	0.069*
H16B	0.698981	0.681399	−0.048533	0.069*
H16C	0.498834	0.641632	−0.082739	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N2	0.028 (2)	0.042 (2)	0.043 (2)	0.0133 (18)	−0.0003 (18)	0.0099 (18)
C1	0.029 (3)	0.041 (3)	0.054 (3)	0.007 (2)	−0.002 (2)	0.012 (2)
C2	0.043 (3)	0.038 (3)	0.040 (3)	0.019 (2)	−0.006 (2)	0.003 (2)
C3	0.037 (3)	0.032 (2)	0.045 (3)	0.011 (2)	−0.004 (2)	0.005 (2)
C4	0.034 (3)	0.038 (3)	0.040 (3)	0.011 (2)	−0.012 (2)	0.003 (2)
C5	0.026 (2)	0.035 (2)	0.030 (2)	0.0110 (19)	0.0023 (19)	0.0060 (19)
C6	0.029 (2)	0.048 (3)	0.038 (3)	0.014 (2)	0.003 (2)	0.010 (2)
O1	0.0231 (16)	0.0437 (18)	0.052 (2)	0.0118 (14)	0.0034 (15)	0.0230 (16)
O2	0.0355 (18)	0.0449 (19)	0.0450 (19)	0.0182 (15)	0.0092 (15)	0.0240 (15)
O3	0.0261 (18)	0.059 (2)	0.077 (3)	0.0020 (17)	0.0009 (18)	−0.021 (2)
O4	0.038 (2)	0.082 (3)	0.041 (2)	−0.0013 (19)	0.0145 (17)	−0.0069 (19)
N3	0.026 (2)	0.033 (2)	0.035 (2)	0.0136 (16)	−0.0006 (17)	0.0111 (17)
C7	0.026 (2)	0.033 (2)	0.026 (2)	0.0103 (19)	0.0016 (18)	0.0073 (18)
C8	0.020 (2)	0.032 (2)	0.028 (2)	0.0066 (18)	0.0028 (18)	0.0055 (18)
C9	0.028 (2)	0.029 (2)	0.036 (2)	0.0105 (18)	0.002 (2)	0.0099 (19)
C10	0.035 (3)	0.035 (2)	0.042 (3)	0.006 (2)	0.009 (2)	0.013 (2)
C11	0.017 (2)	0.046 (3)	0.040 (3)	0.0010 (19)	0.0026 (19)	0.009 (2)
C12	0.019 (2)	0.046 (3)	0.036 (2)	0.0089 (19)	−0.0009 (19)	0.012 (2)
S1	0.0683 (11)	0.0606 (10)	0.0572 (9)	−0.0017 (8)	0.0083 (8)	−0.0007 (7)
C17	0.059 (4)	0.048 (3)	0.078 (4)	−0.006 (3)	0.011 (3)	−0.003 (3)
C18	0.055 (4)	0.052 (3)	0.062 (4)	−0.012 (3)	0.011 (3)	0.005 (3)
C19	0.034 (3)	0.041 (3)	0.054 (3)	−0.008 (2)	0.010 (2)	0.013 (2)
C20	0.036 (3)	0.056 (3)	0.046 (3)	−0.015 (3)	0.012 (2)	0.004 (3)
N1	0.030 (2)	0.0296 (19)	0.037 (2)	0.0074 (16)	0.0045 (17)	0.0079 (16)
C13	0.075 (4)	0.043 (3)	0.040 (3)	0.015 (3)	0.009 (3)	0.005 (2)
C14	0.034 (3)	0.032 (2)	0.037 (2)	0.008 (2)	0.002 (2)	0.0063 (19)
C15	0.035 (3)	0.028 (2)	0.038 (2)	0.009 (2)	0.005 (2)	0.0102 (19)
C16	0.055 (3)	0.030 (2)	0.056 (3)	0.007 (2)	0.010 (3)	0.006 (2)

Geometric parameters (Å, º)

N2—C1	1.325 (6)	C10—C11	1.393 (6)
N2—C2	1.350 (6)	C10—H10	0.9300
C1—C3	1.397 (6)	C11—C12	1.370 (6)
C1—H1A	0.9300	C11—H11	0.9300
C2—C4	1.382 (6)	C12—H12	0.9300
C2—H2A	0.9300	S1—C17	1.701 (6)
C3—C5	1.384 (6)	S1—C20	1.733 (5)
C3—H3	0.9300	C17—C18	1.326 (8)
C4—C5	1.384 (6)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.422 (7)
C5—C6	1.507 (6)	C18—H18	0.9300
C6—C6^i	1.534 (9)	C19—C20	1.396 (7)
C6—H6A	0.9700	C19—H19	0.9300
C6—H6B	0.9700	C20—C20^ii	1.453 (11)
O1—C7	1.339 (5)	N1—C15	1.334 (6)
O1—H1	0.8199	N1—C14	1.342 (5)
O2—C9	1.370 (5)	C13—C14	1.501 (6)
O2—H2	0.8200	C13—H13A	0.9600
O3—N3	1.219 (5)	C13—H13B	0.9600
O4—N3	1.208 (5)	C13—H13C	0.9600
N3—C8	1.471 (5)	C14—C15^iii	1.394 (6)
C7—C8	1.394 (5)	C15—C16	1.498 (6)
C7—C12	1.408 (6)	C16—H16A	0.9600
C8—C9	1.387 (6)	C16—H16B	0.9600
C9—C10	1.379 (6)	C16—H16C	0.9600
C1—N2—C2	116.1 (4)	C12—C11—C10	122.2 (4)
N2—C1—C3	124.2 (4)	C12—C11—H11	118.9
N2—C1—H1A	117.9	C10—C11—H11	118.9
C3—C1—H1A	117.9	C11—C12—C7	120.2 (4)
N2—C2—C4	123.7 (4)	C11—C12—H12	119.9
N2—C2—H2A	118.2	C7—C12—H12	119.9
C4—C2—H2A	118.2	C17—S1—C20	91.7 (3)
C5—C3—C1	119.0 (4)	C18—C17—S1	112.2 (5)
C5—C3—H3	120.5	C18—C17—H17	123.9
C1—C3—H3	120.5	S1—C17—H17	123.9
C2—C4—C5	119.5 (4)	C17—C18—C19	114.9 (6)
C2—C4—H4	120.2	C17—C18—H18	122.6
C5—C4—H4	120.2	C19—C18—H18	122.6
C3—C5—C4	117.5 (4)	C20—C19—C18	110.2 (5)
C3—C5—C6	122.1 (4)	C20—C19—H19	124.9
C4—C5—C6	120.3 (4)	C18—C19—H19	124.9
C5—C6—C6^i	111.8 (5)	C19—C20—C20^ii	128.2 (6)
C5—C6—H6A	109.3	C19—C20—S1	110.9 (4)
C6^i—C6—H6A	109.3	C20^ii—C20—S1	120.8 (5)
C5—C6—H6B	109.3	C15—N1—C14	119.8 (4)
C6^i—C6—H6B	109.3	C14—C13—H13A	109.5
H6A—C6—H6B	107.9	C14—C13—H13B	109.5
C7—O1—H1	109.6	H13A—C13—H13B	109.5
C9—O2—H2	109.4	C14—C13—H13C	109.5
O4—N3—O3	123.1 (4)	H13A—C13—H13C	109.5
O4—N3—C8	118.3 (4)	H13B—C13—H13C	109.5
O3—N3—C8	118.4 (4)	N1—C14—C15^iii	120.5 (4)
O1—C7—C8	118.9 (4)	N1—C14—C13	116.6 (4)
O1—C7—C12	124.5 (4)	C15^iii—C14—C13	122.9 (4)
C8—C7—C12	116.5 (4)	N1—C15—C14^iii	119.7 (4)
C9—C8—C7	123.3 (4)	N1—C15—C16	117.7 (4)
C9—C8—N3	118.5 (4)	C14^iii—C15—C16	122.6 (4)
C7—C8—N3	118.2 (4)	C15—C16—H16A	109.5
O2—C9—C10	124.0 (4)	C15—C16—H16B	109.5
O2—C9—C8	117.0 (4)	H16A—C16—H16B	109.5
C10—C9—C8	119.0 (4)	C15—C16—H16C	109.5
C9—C10—C11	118.8 (4)	H16A—C16—H16C	109.5
C9—C10—H10	120.6	H16B—C16—H16C	109.5
C11—C10—H10	120.6
C2—N2—C1—C3	0.0 (7)	C7—C8—C9—C10	−2.6 (7)
C1—N2—C2—C4	1.0 (7)	N3—C8—C9—C10	177.5 (4)
N2—C1—C3—C5	−0.7 (8)	O2—C9—C10—C11	−179.5 (4)
N2—C2—C4—C5	−1.4 (7)	C8—C9—C10—C11	1.7 (7)
C1—C3—C5—C4	0.3 (7)	C9—C10—C11—C12	0.9 (7)
C1—C3—C5—C6	−179.9 (4)	C10—C11—C12—C7	−2.6 (7)
C2—C4—C5—C3	0.7 (7)	O1—C7—C12—C11	−178.3 (4)
C2—C4—C5—C6	−179.2 (4)	C8—C7—C12—C11	1.7 (6)
C3—C5—C6—C6^i	−104.7 (6)	C20—S1—C17—C18	0.1 (5)
C4—C5—C6—C6^i	75.1 (7)	S1—C17—C18—C19	−0.6 (7)
O1—C7—C8—C9	−179.1 (4)	C17—C18—C19—C20	0.9 (7)
C12—C7—C8—C9	0.9 (6)	C18—C19—C20—C20^ii	178.9 (6)
O1—C7—C8—N3	0.8 (6)	C18—C19—C20—S1	−0.8 (5)
C12—C7—C8—N3	−179.1 (4)	C17—S1—C20—C19	0.4 (4)
O4—N3—C8—C9	−88.5 (5)	C17—S1—C20—C20^ii	−179.3 (6)
O3—N3—C8—C9	87.3 (5)	C15—N1—C14—C15^iii	0.8 (7)
O4—N3—C8—C7	91.5 (5)	C15—N1—C14—C13	−178.0 (4)
O3—N3—C8—C7	−92.6 (5)	C14—N1—C15—C14^iii	−0.8 (7)
C7—C8—C9—O2	178.5 (4)	C14—N1—C15—C16	177.5 (4)
N3—C8—C9—O2	−1.5 (6)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+2, −z; (iii) −x+1, −y+2, −z.

(23NRES-TMP-22TBP-DPE-II)

Crystal data

C40H38N6O8S2	Z = 1
Mr = 794.88	F(000) = 416
Triclinic, P1	Dx = 1.376 Mg m^−3
a = 7.514 (3) Å	Mo Kα radiation, λ = 0.71075 Å
b = 9.272 (3) Å	Cell parameters from 6283 reflections
c = 13.852 (5) Å	θ = 3.1–27.8°
α = 83.832 (7)°	µ = 0.20 mm^−1
β = 89.887 (7)°	T = 150 K
γ = 88.173 (7)°	Block, yellow
V = 958.9 (6) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	1949 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.060
profile data from ω–scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −8→8
Tmin = 0.680, Tmax = 1.000	k = −11→11
7607 measured reflections	l = −16→16
3352 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.078	H-atom parameters constrained
wR(F^2) = 0.242	w = 1/[σ^2(Fo^2) + (0.0844P)^2 + 1.4085P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
3352 reflections	Δρmax = 0.33 e Å^−3
255 parameters	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.4549 (3)	0.6806 (2)	0.88675 (13)	0.0855 (7)
C15	0.4254 (7)	0.6582 (6)	1.0729 (4)	0.0545 (14)
H15	0.425706	0.623078	1.138384	0.065*
C16	0.4711 (7)	0.5761 (6)	0.9965 (4)	0.0583 (15)
C13	0.3899 (9)	0.8278 (8)	0.9397 (6)	0.081 (2)
H13	0.364003	0.918041	0.905753	0.098*
C14	0.3795 (9)	0.8009 (8)	1.0358 (5)	0.0769 (19)
H14	0.344279	0.871635	1.075361	0.092*
O3	0.1468 (4)	−0.1418 (4)	0.6242 (3)	0.0510 (10)
H3	0.238364	−0.185294	0.610227	0.076*
O4	−0.0720 (4)	0.2514 (4)	0.7796 (3)	0.0543 (10)
H4	−0.040830	0.318842	0.808677	0.081*
C1	0.0477 (6)	0.0608 (5)	0.6999 (3)	0.0362 (11)
N3	0.9876 (5)	0.5835 (4)	0.0751 (3)	0.0428 (10)
N2	−0.1354 (5)	0.0268 (5)	0.6766 (3)	0.0440 (10)
C18	0.9620 (6)	0.6439 (5)	−0.0153 (4)	0.0408 (12)
N1	0.4509 (6)	0.7004 (5)	0.5911 (3)	0.0479 (11)
C2	0.0739 (6)	0.1778 (5)	0.7507 (3)	0.0395 (11)
C6	0.1882 (6)	−0.0274 (5)	0.6701 (3)	0.0366 (11)
C5	0.3599 (6)	0.0104 (5)	0.6911 (4)	0.0442 (12)
H5	0.456960	−0.045350	0.673056	0.053*
C4	0.3861 (7)	0.1311 (6)	0.7388 (4)	0.0506 (14)
H4A	0.501912	0.157644	0.750217	0.061*
O2	−0.2137 (6)	−0.0569 (5)	0.7317 (4)	0.0940 (17)
C11	0.7723 (6)	0.5568 (5)	0.5507 (3)	0.0409 (12)
C3	0.2470 (7)	0.2132 (6)	0.7700 (4)	0.0518 (14)
H3A	0.268661	0.292136	0.803900	0.062*
C12	0.9351 (7)	0.4761 (5)	0.5277 (3)	0.0453 (13)
H12	0.946805	0.380556	0.555795	0.054*
C19	1.0264 (7)	0.4402 (5)	0.0923 (4)	0.0428 (12)
C9	0.6427 (7)	0.4898 (6)	0.6081 (4)	0.0469 (13)
H9	0.660616	0.394042	0.634719	0.056*
C10	0.7351 (7)	0.6995 (5)	0.5149 (4)	0.0513 (14)
H10	0.817659	0.750957	0.475983	0.062*
C7	0.4856 (7)	0.5644 (6)	0.6265 (4)	0.0474 (13)
H7	0.400498	0.516437	0.665582	0.057*
C8	0.5765 (8)	0.7649 (6)	0.5369 (4)	0.0559 (15)
H8	0.555588	0.861222	0.512101	0.067*
O1	−0.2028 (6)	0.0918 (6)	0.6056 (3)	0.0919 (16)
C20	1.0497 (10)	0.3791 (7)	0.1961 (4)	0.0716 (18)
H20A	1.000226	0.446456	0.237670	0.107*
H20B	1.174221	0.362521	0.210112	0.107*
H20C	0.989615	0.288945	0.207179	0.107*
C17	0.9163 (8)	0.8033 (5)	−0.0295 (4)	0.0583 (15)
H17A	0.793654	0.817900	−0.048497	0.088*
H17B	0.990700	0.849492	−0.079238	0.088*
H17C	0.935095	0.844578	0.030181	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0954 (15)	0.0959 (14)	0.0646 (11)	−0.0098 (11)	0.0010 (10)	−0.0031 (10)
C15	0.047 (3)	0.058 (4)	0.061 (4)	−0.010 (3)	−0.004 (3)	−0.014 (3)
C16	0.043 (3)	0.078 (4)	0.055 (3)	−0.020 (3)	−0.005 (3)	−0.007 (3)
C13	0.074 (5)	0.077 (5)	0.093 (6)	−0.010 (4)	−0.005 (4)	−0.003 (4)
C14	0.067 (4)	0.095 (5)	0.073 (5)	−0.015 (4)	−0.007 (4)	−0.023 (4)
O3	0.038 (2)	0.048 (2)	0.071 (2)	0.0091 (16)	0.0033 (17)	−0.0297 (19)
O4	0.044 (2)	0.057 (2)	0.066 (2)	0.0142 (17)	0.0009 (18)	−0.0306 (19)
C1	0.030 (2)	0.041 (3)	0.037 (3)	0.005 (2)	0.001 (2)	−0.006 (2)
N3	0.049 (3)	0.037 (2)	0.044 (2)	0.0031 (19)	0.0019 (19)	−0.0134 (19)
N2	0.035 (2)	0.048 (3)	0.050 (3)	0.013 (2)	−0.003 (2)	−0.013 (2)
C18	0.040 (3)	0.034 (3)	0.049 (3)	0.003 (2)	−0.002 (2)	−0.010 (2)
N1	0.047 (3)	0.049 (3)	0.050 (3)	0.007 (2)	0.010 (2)	−0.014 (2)
C2	0.039 (3)	0.040 (3)	0.041 (3)	0.007 (2)	0.000 (2)	−0.013 (2)
C6	0.038 (3)	0.038 (3)	0.035 (3)	0.001 (2)	0.003 (2)	−0.010 (2)
C5	0.034 (3)	0.046 (3)	0.054 (3)	0.010 (2)	0.005 (2)	−0.013 (2)
C4	0.036 (3)	0.062 (3)	0.057 (3)	−0.004 (3)	0.004 (2)	−0.016 (3)
O2	0.043 (3)	0.093 (3)	0.133 (4)	−0.013 (2)	−0.004 (3)	0.048 (3)
C11	0.044 (3)	0.044 (3)	0.034 (3)	0.009 (2)	0.003 (2)	−0.010 (2)
C3	0.049 (3)	0.052 (3)	0.058 (3)	−0.005 (3)	−0.002 (3)	−0.025 (3)
C12	0.046 (3)	0.039 (3)	0.048 (3)	0.012 (2)	0.002 (2)	0.000 (2)
C19	0.043 (3)	0.041 (3)	0.046 (3)	0.001 (2)	−0.001 (2)	−0.009 (2)
C9	0.048 (3)	0.044 (3)	0.048 (3)	0.010 (2)	0.003 (2)	−0.003 (2)
C10	0.051 (3)	0.041 (3)	0.060 (3)	0.012 (2)	0.019 (3)	−0.003 (3)
C7	0.045 (3)	0.050 (3)	0.048 (3)	0.003 (2)	0.005 (2)	−0.009 (3)
C8	0.063 (4)	0.042 (3)	0.061 (4)	0.021 (3)	0.015 (3)	−0.007 (3)
O1	0.061 (3)	0.146 (5)	0.063 (3)	−0.013 (3)	−0.024 (2)	0.018 (3)
C20	0.098 (5)	0.059 (4)	0.056 (4)	0.010 (3)	−0.002 (3)	−0.004 (3)
C17	0.067 (4)	0.037 (3)	0.072 (4)	0.007 (3)	−0.013 (3)	−0.014 (3)

Geometric parameters (Å, º)

S1—C13	1.676 (8)	C18—C19^ii	1.388 (7)
S1—C16	1.716 (6)	C18—C17	1.499 (7)
C15—C14	1.400 (9)	N1—C7	1.321 (6)
C15—C16	1.405 (8)	N1—C8	1.322 (7)
C16—C16^i	1.456 (12)	C2—C3	1.385 (7)
C13—C14	1.330 (9)	C6—C5	1.387 (7)
O3—C6	1.339 (5)	C5—C4	1.379 (7)
O4—C2	1.356 (5)	C4—C3	1.369 (7)
C1—C2	1.374 (6)	C11—C9	1.377 (7)
C1—C6	1.404 (6)	C11—C10	1.382 (7)
C1—N2	1.465 (6)	C11—C12	1.466 (6)
N3—C18	1.328 (6)	C12—C12^iii	1.299 (9)
N3—C19	1.347 (6)	C19—C20	1.497 (7)
N2—O2	1.196 (5)	C9—C7	1.386 (7)
N2—O1	1.201 (6)	C10—C8	1.369 (7)
C13—S1—C16	92.0 (3)	O4—C2—C3	123.8 (4)
C14—C15—C16	109.9 (6)	C1—C2—C3	118.4 (4)
C15—C16—C16^i	127.6 (7)	O3—C6—C5	125.0 (4)
C15—C16—S1	110.8 (5)	O3—C6—C1	117.7 (4)
C16^i—C16—S1	121.6 (6)	C5—C6—C1	117.3 (4)
C14—C13—S1	112.4 (6)	C4—C5—C6	119.7 (4)
C13—C14—C15	114.9 (7)	C3—C4—C5	122.1 (5)
C2—C1—C6	122.8 (4)	C9—C11—C10	116.0 (4)
C2—C1—N2	118.3 (4)	C9—C11—C12	120.4 (4)
C6—C1—N2	118.9 (4)	C10—C11—C12	123.6 (4)
C18—N3—C19	119.9 (4)	C4—C3—C2	119.6 (5)
O2—N2—O1	123.3 (5)	C12^iii—C12—C11	126.9 (6)
O2—N2—C1	118.9 (4)	N3—C19—C18^ii	119.8 (4)
O1—N2—C1	117.7 (5)	N3—C19—C20	117.0 (4)
N3—C18—C19^ii	120.3 (4)	C18^ii—C19—C20	123.2 (5)
N3—C18—C17	117.4 (4)	C11—C9—C7	120.3 (5)
C19^ii—C18—C17	122.3 (5)	C8—C10—C11	119.8 (5)
C7—N1—C8	116.4 (4)	N1—C7—C9	123.1 (5)
O4—C2—C1	117.8 (4)	N1—C8—C10	124.4 (5)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y+1, −z; (iii) −x+2, −y+1, −z+1.

(24NRES-TMP-22BP-22TBP-DPE-I)

Crystal data

C41H41N7O8S	Z = 1
Mr = 791.87	F(000) = 416
Triclinic, P1	Dx = 1.345 Mg m^−3
a = 7.4741 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2215 (19) Å	Cell parameters from 7836 reflections
c = 14.295 (3) Å	θ = 3.0–27.6°
α = 96.245 (7)°	µ = 0.15 mm^−1
β = 92.609 (7)°	T = 150 K
γ = 92.314 (7)°	Block, colorless
V = 977.4 (3) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3102 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.051
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.659, Tmax = 1.000	k = −11→11
9903 measured reflections	l = −18→18
4424 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.070	w = 1/[σ^2(Fo^2) + (0.0453P)^2 + 0.7428P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.170	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 0.23 e Å^−3
4424 reflections	Δρmin = −0.28 e Å^−3
284 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.015 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.3046 (3)	−0.0630 (2)	0.76531 (16)	0.0484 (6)
O4	0.6773 (2)	−0.1253 (2)	0.87982 (14)	0.0354 (5)
H4	0.766227	−0.173305	0.885983	0.053*
O3	0.4520 (2)	0.2504 (2)	0.71538 (13)	0.0361 (5)
H3	0.474644	0.294543	0.670228	0.054*
O2	0.3323 (3)	0.0888 (3)	0.89189 (14)	0.0473 (6)
C1	0.5771 (3)	0.0671 (3)	0.79747 (17)	0.0254 (6)
N3	−0.5206 (3)	−0.4174 (2)	0.42577 (15)	0.0272 (5)
C7	−0.5355 (4)	−0.3785 (3)	0.69120 (19)	0.0399 (7)
H7A	−0.653083	−0.341975	0.698533	0.060*
H7B	−0.447117	−0.300289	0.707684	0.060*
H7C	−0.517601	−0.453664	0.731694	0.060*
C13	0.1527 (4)	−0.4930 (3)	0.89083 (19)	0.0347 (7)
H13	0.161014	−0.590677	0.867833	0.042*
N1	−0.0303 (3)	−0.2841 (3)	0.91280 (16)	0.0329 (6)
C9	−0.5390 (3)	−0.3562 (3)	0.51438 (18)	0.0259 (6)
N2	0.3912 (3)	0.0265 (2)	0.81988 (15)	0.0264 (5)
C19	−0.0795 (4)	−0.3354 (3)	0.4457 (2)	0.0378 (7)
H19	−0.085922	−0.368162	0.381712	0.045*
C17	−0.1104 (4)	−0.1562 (4)	0.5744 (3)	0.0475 (8)
C5	0.8926 (4)	0.0344 (3)	0.8109 (2)	0.0345 (7)
H5	0.990539	−0.014201	0.832180	0.041*
C10	−0.5863 (4)	−0.1983 (3)	0.5279 (2)	0.0329 (6)
H10A	−0.561832	−0.153482	0.471961	0.049*
H10B	−0.515860	−0.148486	0.580394	0.049*
H10C	−0.711270	−0.192321	0.539783	0.049*
C8	−0.5176 (3)	−0.4401 (3)	0.59065 (18)	0.0274 (6)
C12	0.3023 (3)	−0.4149 (3)	0.93588 (17)	0.0270 (6)
C6	0.7179 (3)	−0.0117 (3)	0.83059 (18)	0.0277 (6)
C15	0.2791 (4)	−0.2701 (3)	0.96993 (19)	0.0320 (6)
H15	0.374137	−0.213643	1.001115	0.038*
C14	−0.0089 (4)	−0.4248 (3)	0.8803 (2)	0.0342 (6)
H14	−0.106316	−0.478762	0.849536	0.041*
C4	0.9189 (4)	0.1530 (3)	0.75949 (19)	0.0336 (6)
H4A	1.035223	0.182570	0.747400	0.040*
C2	0.6011 (3)	0.1854 (3)	0.74473 (18)	0.0276 (6)
C11	0.4811 (4)	−0.4839 (3)	0.94871 (18)	0.0323 (6)
H11A	0.575951	−0.418788	0.931134	0.039*
H11B	0.481705	−0.574332	0.907124	0.039*
C16	0.1143 (4)	−0.2106 (3)	0.95720 (19)	0.0351 (7)
H16	0.102433	−0.113618	0.980776	0.042*
C18	−0.1231 (4)	−0.1947 (4)	0.4789 (3)	0.0457 (8)
H18	−0.159614	−0.128920	0.437764	0.055*
C3	0.7764 (4)	0.2284 (3)	0.72574 (19)	0.0337 (6)
H3A	0.797367	0.306492	0.690989	0.040*
C20	−0.0261 (4)	−0.4241 (3)	0.5126 (2)	0.0331 (6)
S1	−0.0328 (4)	−0.3253 (6)	0.61324 (19)	0.0750 (12)	0.5
C17A	−0.0589 (9)	−0.2387 (7)	0.6481 (5)	0.0352 (16)	0.5
N17B	−0.0117 (18)	−0.3937 (11)	0.6151 (10)	0.085 (5)	0.5
H1	−0.056 (5)	−0.214 (5)	0.714 (3)	0.003 (10)*	0.5
H17	−0.128 (5)	−0.064 (4)	0.601 (3)	0.069 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0254 (11)	0.0508 (14)	0.0627 (14)	−0.0047 (10)	−0.0012 (10)	−0.0177 (11)
O4	0.0231 (10)	0.0411 (12)	0.0466 (12)	0.0098 (9)	0.0012 (9)	0.0231 (9)
O3	0.0315 (10)	0.0433 (12)	0.0380 (11)	0.0141 (9)	0.0035 (8)	0.0197 (9)
O2	0.0310 (11)	0.0740 (16)	0.0344 (11)	−0.0028 (11)	0.0088 (9)	−0.0061 (11)
C1	0.0183 (12)	0.0323 (14)	0.0261 (13)	0.0019 (11)	−0.0007 (10)	0.0059 (10)
N3	0.0261 (11)	0.0282 (12)	0.0283 (11)	0.0059 (9)	0.0005 (9)	0.0064 (9)
C7	0.0520 (19)	0.0392 (17)	0.0291 (14)	0.0086 (15)	0.0004 (13)	0.0044 (12)
C13	0.0330 (15)	0.0325 (15)	0.0384 (15)	0.0074 (13)	−0.0029 (12)	0.0033 (12)
N1	0.0254 (12)	0.0398 (14)	0.0353 (12)	0.0080 (11)	−0.0025 (10)	0.0119 (10)
C9	0.0204 (12)	0.0265 (13)	0.0318 (13)	0.0029 (11)	0.0007 (10)	0.0076 (10)
N2	0.0191 (10)	0.0321 (12)	0.0289 (11)	0.0041 (9)	−0.0006 (9)	0.0070 (9)
C19	0.0268 (14)	0.0334 (16)	0.0547 (18)	−0.0031 (13)	0.0064 (13)	0.0115 (13)
C17	0.0323 (17)	0.045 (2)	0.065 (2)	−0.0041 (15)	0.0036 (15)	0.0080 (17)
C5	0.0219 (13)	0.0458 (17)	0.0390 (15)	0.0102 (13)	−0.0013 (11)	0.0168 (13)
C10	0.0328 (15)	0.0260 (14)	0.0411 (15)	0.0061 (12)	0.0034 (12)	0.0060 (11)
C8	0.0240 (13)	0.0296 (14)	0.0292 (13)	0.0037 (11)	−0.0017 (10)	0.0057 (11)
C12	0.0248 (13)	0.0335 (14)	0.0248 (12)	0.0091 (11)	0.0003 (10)	0.0102 (11)
C6	0.0230 (13)	0.0344 (15)	0.0277 (13)	0.0055 (11)	0.0003 (10)	0.0110 (11)
C15	0.0273 (14)	0.0329 (15)	0.0352 (15)	0.0036 (12)	−0.0082 (11)	0.0042 (12)
C14	0.0250 (14)	0.0370 (16)	0.0405 (15)	−0.0008 (12)	−0.0059 (12)	0.0069 (12)
C4	0.0212 (13)	0.0471 (17)	0.0345 (14)	0.0005 (12)	0.0011 (11)	0.0139 (13)
C2	0.0254 (13)	0.0312 (14)	0.0271 (13)	0.0071 (11)	−0.0016 (10)	0.0067 (11)
C11	0.0260 (13)	0.0442 (17)	0.0286 (14)	0.0117 (12)	−0.0004 (11)	0.0103 (12)
C16	0.0375 (16)	0.0330 (15)	0.0353 (15)	0.0120 (13)	−0.0061 (12)	0.0050 (12)
C18	0.0326 (16)	0.0389 (18)	0.066 (2)	−0.0038 (14)	0.0039 (15)	0.0108 (16)
C3	0.0308 (15)	0.0373 (16)	0.0354 (15)	0.0021 (13)	0.0038 (12)	0.0145 (12)
C20	0.0241 (13)	0.0324 (15)	0.0417 (16)	−0.0049 (12)	0.0053 (11)	−0.0004 (13)
S1	0.0518 (16)	0.134 (4)	0.0361 (13)	−0.031 (2)	−0.0008 (11)	0.0082 (19)
C17A	0.047 (4)	0.028 (3)	0.027 (3)	0.007 (3)	0.003 (3)	−0.012 (3)
N17B	0.083 (7)	0.065 (7)	0.112 (9)	0.021 (5)	0.035 (5)	0.015 (5)

Geometric parameters (Å, º)

O1—N2	1.217 (3)	C17—C18	1.370 (5)
O4—C6	1.356 (3)	C17—C17A	1.415 (7)
O3—C2	1.358 (3)	C17—S1	1.819 (6)
O2—N2	1.231 (3)	C5—C4	1.395 (4)
C1—C6	1.397 (3)	C5—C6	1.407 (4)
C1—C2	1.403 (4)	C12—C15	1.391 (4)
C1—N2	1.482 (3)	C12—C11	1.515 (3)
N3—C9	1.345 (3)	C15—C16	1.381 (4)
N3—C8^i	1.354 (3)	C4—C3	1.392 (4)
C7—C8	1.501 (4)	C2—C3	1.401 (4)
C13—C14	1.394 (4)	C11—C11^ii	1.543 (5)
C13—C12	1.397 (4)	C20—N17B	1.459 (14)
N1—C16	1.348 (4)	C20—C20^iii	1.480 (5)
N1—C14	1.348 (4)	C20—S1	1.621 (4)
C9—C8	1.411 (4)	S1—N17B	0.659 (10)
C9—C10	1.507 (4)	S1—C17A	0.927 (6)
C19—C20	1.380 (4)	C17A—N17B	1.516 (11)
C19—C18	1.389 (4)
C6—C1—C2	123.6 (2)	N1—C14—C13	122.9 (3)
C6—C1—N2	119.0 (2)	C3—C4—C5	122.0 (3)
C2—C1—N2	117.3 (2)	O3—C2—C3	124.4 (2)
C9—N3—C8^i	120.1 (2)	O3—C2—C1	117.5 (2)
C14—C13—C12	120.1 (3)	C3—C2—C1	118.1 (2)
C16—N1—C14	116.4 (2)	C12—C11—C11^ii	111.9 (3)
N3—C9—C8	120.1 (2)	N1—C16—C15	124.2 (3)
N3—C9—C10	117.6 (2)	C17—C18—C19	117.7 (3)
C8—C9—C10	122.2 (2)	C4—C3—C2	119.2 (3)
O1—N2—O2	123.9 (2)	C19—C20—N17B	129.6 (5)
O1—N2—C1	118.5 (2)	C19—C20—C20^iii	122.4 (3)
O2—N2—C1	117.6 (2)	N17B—C20—C20^iii	108.0 (5)
C20—C19—C18	116.5 (3)	C19—C20—S1	105.7 (3)
C18—C17—C17A	130.0 (4)	N17B—C20—S1	24.0 (4)
C18—C17—S1	99.9 (3)	C20^iii—C20—S1	131.9 (4)
C17A—C17—S1	30.1 (3)	N17B—S1—C17A	145.3 (16)
C4—C5—C6	120.0 (2)	N17B—S1—C20	64.1 (14)
N3^i—C8—C9	119.7 (2)	C17A—S1—C20	150.2 (6)
N3^i—C8—C7	117.4 (2)	N17B—S1—C17	163.9 (14)
C9—C8—C7	122.8 (2)	C17A—S1—C17	50.0 (5)
C15—C12—C13	116.7 (2)	C20—S1—C17	100.2 (2)
C15—C12—C11	121.1 (2)	S1—C17A—C17	99.8 (7)
C13—C12—C11	122.1 (2)	S1—C17A—N17B	14.3 (7)
O4—C6—C1	118.1 (2)	C17—C17A—N17B	114.0 (7)
O4—C6—C5	124.8 (2)	S1—N17B—C20	91.9 (15)
C1—C6—C5	117.1 (2)	S1—N17B—C17A	20.3 (10)
C16—C15—C12	119.7 (3)	C20—N17B—C17A	112.1 (8)

Symmetry codes: (i) −x−1, −y−1, −z+1; (ii) −x+1, −y−1, −z+2; (iii) −x, −y−1, −z+1.

(25NRES-TMP-22BP-22TBP-DPE-II)

Crystal data

C41H39N7O8S	Z = 1
Mr = 789.85	F(000) = 414
Triclinic, P1	Dx = 1.379 Mg m^−3
a = 7.4078 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3192 (15) Å	Cell parameters from 7341 reflections
c = 13.815 (2) Å	θ = 3.1–27.6°
α = 94.239 (7)°	µ = 0.15 mm^−1
β = 91.445 (6)°	T = 150 K
γ = 90.299 (6)°	Block, colorless
V = 950.8 (3) Å^3	0.10 × 0.07 × 0.05 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2799 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.044
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.812, Tmax = 1.000	k = −12→12
9734 measured reflections	l = −17→17
4336 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.058	w = 1/[σ^2(Fo^2) + (0.0563P)^2 + 0.4009P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.146	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.27 e Å^−3
4336 reflections	Δρmin = −0.36 e Å^−3
293 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
174 restraints	Extinction coefficient: 0.011 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O4	0.6433 (2)	0.64374 (17)	0.12183 (12)	0.0320 (4)
H4	0.738463	0.687582	0.109558	0.048*
O1	0.4240 (2)	0.24695 (17)	0.27519 (12)	0.0322 (4)
H1	0.453552	0.193892	0.319460	0.048*
N2	0.3576 (2)	0.48036 (19)	0.17526 (14)	0.0261 (4)
N1	0.5126 (2)	0.08228 (19)	0.42214 (13)	0.0249 (4)
N3	0.9500 (2)	0.7970 (2)	0.09144 (13)	0.0286 (4)
O2	0.2830 (2)	0.4222 (2)	0.10341 (13)	0.0545 (6)
O3	0.2854 (2)	0.5662 (2)	0.23126 (16)	0.0564 (6)
C8	0.6858 (3)	0.5236 (2)	0.16592 (15)	0.0245 (5)
C9	0.5450 (3)	0.4398 (2)	0.19608 (15)	0.0233 (5)
C10	0.5724 (3)	0.3167 (2)	0.24643 (15)	0.0249 (5)
C3	1.2717 (3)	0.9420 (2)	0.05052 (15)	0.0247 (5)
C15	0.5420 (3)	0.1421 (2)	0.51243 (16)	0.0244 (5)
C14	0.4721 (3)	−0.0589 (2)	0.40793 (16)	0.0251 (5)
C6	1.4340 (3)	1.0241 (2)	0.02852 (16)	0.0275 (5)
H6	1.445520	1.119526	0.057467	0.033*
C1	0.9849 (3)	0.9324 (2)	0.12778 (17)	0.0291 (5)
H1A	0.897895	0.979401	0.168126	0.035*
C7	0.8612 (3)	0.4779 (2)	0.18412 (17)	0.0298 (5)
H7	0.960930	0.531226	0.163414	0.036*
C4	1.2368 (3)	0.8013 (2)	0.01448 (17)	0.0288 (5)
H4A	1.322465	0.750730	−0.024887	0.035*
C2	1.1405 (3)	1.0068 (2)	0.10949 (16)	0.0277 (5)
H2	1.158388	1.102339	0.137150	0.033*
C11	0.7492 (3)	0.2745 (2)	0.26437 (16)	0.0302 (5)
H11	0.772852	0.191282	0.298285	0.036*
C5	1.0772 (3)	0.7352 (2)	0.03612 (17)	0.0313 (5)
H5	1.056514	0.639209	0.009872	0.038*
C12	0.8902 (3)	0.3548 (3)	0.23241 (17)	0.0314 (5)
H12	1.010602	0.324553	0.243919	0.038*
C16	0.5931 (3)	0.2988 (2)	0.52371 (18)	0.0334 (6)
H16A	0.723330	0.308418	0.537177	0.050*
H16B	0.527417	0.346359	0.577658	0.050*
H16C	0.562005	0.343865	0.463669	0.050*
C13	0.4429 (4)	−0.1190 (3)	0.30502 (17)	0.0377 (6)
H13A	0.316111	−0.147826	0.294453	0.056*
H13B	0.520348	−0.202883	0.292552	0.056*
H13C	0.473112	−0.045434	0.260769	0.056*
S1	0.9630 (9)	0.8522 (6)	0.3867 (4)	0.0383 (16)	0.25
C20	0.9725 (3)	0.9247 (2)	0.48836 (17)	0.0298 (5)
C19	0.9239 (3)	0.8333 (3)	0.55728 (19)	0.0345 (6)
H19	0.923337	0.864610	0.624285	0.041*
C18	0.8755 (3)	0.6932 (3)	0.5248 (2)	0.0394 (6)
H18	0.841107	0.625584	0.569258	0.047*
C17	0.8788 (4)	0.6547 (3)	0.4266 (2)	0.0443 (7)
C21	0.9262 (15)	0.7354 (10)	0.3558 (8)	0.047 (2)	0.5
S1'	0.9408 (12)	0.7923 (8)	0.3760 (6)	0.071 (2)	0.25
N4	0.9767 (18)	0.9010 (8)	0.3933 (9)	0.052 (3)	0.5
H17	0.846 (4)	0.556 (3)	0.398 (2)	0.065 (9)*
H1B	0.930 (5)	0.729 (4)	0.283 (3)	0.003 (9)*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0214 (8)	0.0322 (9)	0.0447 (10)	−0.0050 (7)	0.0040 (7)	0.0168 (8)
O1	0.0282 (8)	0.0349 (9)	0.0357 (9)	−0.0109 (7)	0.0016 (7)	0.0177 (8)
N2	0.0218 (9)	0.0255 (10)	0.0318 (11)	−0.0065 (8)	0.0041 (8)	0.0063 (9)
N1	0.0260 (9)	0.0227 (9)	0.0266 (10)	−0.0039 (7)	0.0021 (8)	0.0045 (8)
N3	0.0262 (10)	0.0289 (10)	0.0324 (11)	−0.0051 (8)	0.0033 (8)	0.0121 (9)
O2	0.0321 (10)	0.0930 (16)	0.0352 (10)	0.0038 (10)	−0.0103 (8)	−0.0125 (11)
O3	0.0279 (10)	0.0508 (12)	0.0851 (15)	0.0036 (8)	0.0012 (10)	−0.0304 (12)
C8	0.0248 (11)	0.0246 (11)	0.0248 (11)	−0.0034 (9)	0.0036 (9)	0.0054 (9)
C9	0.0202 (10)	0.0269 (11)	0.0232 (11)	−0.0022 (9)	0.0013 (8)	0.0049 (9)
C10	0.0238 (11)	0.0282 (12)	0.0235 (11)	−0.0057 (9)	0.0030 (9)	0.0071 (9)
C3	0.0248 (11)	0.0270 (11)	0.0230 (11)	−0.0051 (9)	0.0003 (9)	0.0070 (9)
C15	0.0222 (11)	0.0227 (11)	0.0286 (12)	−0.0029 (8)	0.0010 (9)	0.0033 (9)
C14	0.0256 (11)	0.0246 (11)	0.0256 (11)	−0.0020 (9)	0.0024 (9)	0.0047 (9)
C6	0.0288 (12)	0.0233 (11)	0.0304 (12)	−0.0058 (9)	0.0023 (9)	0.0013 (10)
C1	0.0255 (11)	0.0334 (13)	0.0293 (12)	−0.0020 (9)	0.0056 (9)	0.0068 (10)
C7	0.0204 (11)	0.0343 (13)	0.0362 (13)	−0.0043 (9)	0.0062 (9)	0.0116 (11)
C4	0.0299 (12)	0.0250 (11)	0.0321 (13)	−0.0046 (9)	0.0083 (10)	0.0046 (10)
C2	0.0295 (12)	0.0251 (11)	0.0286 (12)	−0.0048 (9)	0.0022 (9)	0.0016 (10)
C11	0.0316 (12)	0.0307 (12)	0.0298 (12)	0.0012 (10)	0.0013 (10)	0.0112 (10)
C5	0.0328 (13)	0.0247 (12)	0.0371 (13)	−0.0059 (10)	0.0043 (10)	0.0059 (10)
C12	0.0224 (11)	0.0391 (14)	0.0339 (13)	0.0025 (10)	0.0030 (9)	0.0095 (11)
C16	0.0362 (13)	0.0262 (12)	0.0379 (14)	−0.0071 (10)	−0.0002 (11)	0.0037 (11)
C13	0.0524 (16)	0.0329 (13)	0.0277 (13)	−0.0063 (11)	−0.0005 (11)	0.0031 (11)
S1	0.047 (3)	0.040 (5)	0.0260 (18)	0.002 (4)	−0.0013 (16)	−0.014 (3)
C20	0.0253 (11)	0.0334 (13)	0.0302 (13)	0.0052 (10)	−0.0007 (9)	−0.0019 (11)
C19	0.0278 (12)	0.0330 (13)	0.0432 (14)	0.0057 (10)	−0.0002 (10)	0.0070 (11)
C18	0.0331 (13)	0.0355 (14)	0.0501 (16)	0.0004 (11)	−0.0018 (11)	0.0082 (12)
C17	0.0387 (15)	0.0419 (16)	0.0531 (17)	0.0025 (12)	0.0024 (13)	0.0074 (14)
C21	0.049 (2)	0.045 (3)	0.048 (3)	−0.0023 (14)	0.0019 (14)	−0.0002 (14)
S1'	0.067 (4)	0.078 (6)	0.072 (5)	0.010 (5)	0.009 (3)	0.027 (5)
N4	0.061 (4)	0.021 (4)	0.072 (5)	−0.013 (3)	0.000 (3)	−0.010 (3)

Geometric parameters (Å, º)

O4—C8	1.348 (2)	C11—C12	1.381 (3)
O4—H4	0.8400	C11—H11	0.9500
O1—C10	1.357 (2)	C5—H5	0.9500
O1—H1	0.8400	C12—H12	0.9500
N2—O3	1.208 (2)	C16—H16A	0.9800
N2—O2	1.214 (2)	C16—H16B	0.9800
N2—C9	1.468 (3)	C16—H16C	0.9800
N1—C15	1.340 (3)	C13—H13A	0.9800
N1—C14	1.347 (3)	C13—H13B	0.9800
N3—C5	1.335 (3)	C13—H13C	0.9800
N3—C1	1.345 (3)	S1—C21	1.168 (11)
C8—C9	1.390 (3)	S1—C20	1.513 (6)
C8—C7	1.392 (3)	S1—C17	2.058 (7)
C9—C10	1.399 (3)	S1—H1B	1.78 (4)
C10—C11	1.391 (3)	C20—N4	1.317 (13)
C3—C4	1.389 (3)	C20—C19	1.377 (3)
C3—C2	1.395 (3)	C20—C20^iii	1.469 (5)
C3—C6	1.472 (3)	C20—S1'	1.919 (9)
C15—C14^i	1.398 (3)	C19—C18	1.391 (3)
C15—C16	1.503 (3)	C19—H19	0.9500
C14—C13	1.499 (3)	C18—C17	1.378 (4)
C6—C6^ii	1.330 (4)	C18—H18	0.9500
C6—H6	0.9500	C17—C21	1.330 (11)
C1—C2	1.380 (3)	C17—S1'	1.576 (8)
C1—H1A	0.9500	C17—H17	1.00 (3)
C7—C12	1.385 (3)	C21—S1'	0.589 (10)
C7—H7	0.9500	C21—N4	1.630 (12)
C4—C5	1.380 (3)	C21—H1B	1.01 (4)
C4—H4A	0.9500	S1'—N4	1.055 (11)
C2—H2	0.9500	S1'—H1B	1.38 (4)
C8—O4—H4	109.5	C14—C13—H13B	109.5
C10—O1—H1	109.5	H13A—C13—H13B	109.5
O3—N2—O2	123.9 (2)	C14—C13—H13C	109.5
O3—N2—C9	118.59 (19)	H13A—C13—H13C	109.5
O2—N2—C9	117.50 (18)	H13B—C13—H13C	109.5
C15—N1—C14	119.94 (18)	C21—S1—C20	133.1 (9)
C5—N3—C1	115.99 (18)	C21—S1—C17	37.2 (6)
O4—C8—C9	117.92 (19)	C20—S1—C17	96.0 (3)
O4—C8—C7	124.56 (18)	C21—S1—H1B	32.3 (12)
C9—C8—C7	117.52 (19)	C20—S1—H1B	165.3 (13)
C8—C9—C10	123.06 (19)	C17—S1—H1B	69.4 (12)
C8—C9—N2	119.60 (18)	N4—C20—C19	129.5 (4)
C10—C9—N2	117.33 (17)	N4—C20—C20^iii	107.0 (4)
O1—C10—C11	124.43 (19)	C19—C20—C20^iii	123.5 (3)
O1—C10—C9	117.53 (18)	C19—C20—S1	112.3 (3)
C11—C10—C9	118.04 (18)	C20^iii—C20—S1	124.2 (4)
C4—C3—C2	116.30 (19)	N4—C20—S1'	31.6 (5)
C4—C3—C6	123.95 (19)	C19—C20—S1'	97.9 (3)
C2—C3—C6	119.7 (2)	C20^iii—C20—S1'	138.6 (4)
N1—C15—C14^i	120.20 (19)	C20—C19—C18	117.3 (2)
N1—C15—C16	117.63 (19)	C20—C19—H19	121.3
C14^i—C15—C16	122.2 (2)	C18—C19—H19	121.3
N1—C14—C15^i	119.8 (2)	C17—C18—C19	118.4 (3)
N1—C14—C13	117.12 (19)	C17—C18—H18	120.8
C15^i—C14—C13	123.0 (2)	C19—C18—H18	120.8
C6^ii—C6—C3	125.4 (3)	C21—C17—C18	128.0 (5)
C6^ii—C6—H6	117.3	C21—C17—S1'	21.3 (5)
C3—C6—H6	117.3	C18—C17—S1'	106.8 (4)
N3—C1—C2	123.4 (2)	C21—C17—S1	32.0 (4)
N3—C1—H1A	118.3	C18—C17—S1	96.0 (2)
C2—C1—H1A	118.3	C21—C17—H17	109.5 (18)
C12—C7—C8	120.0 (2)	C18—C17—H17	122.5 (18)
C12—C7—H7	120.0	S1'—C17—H17	130.7 (18)
C8—C7—H7	120.0	S1—C17—H17	141.5 (18)
C5—C4—C3	119.7 (2)	S1'—C21—C17	103.7 (16)
C5—C4—H4A	120.2	S1—C21—C17	110.8 (9)
C3—C4—H4A	120.2	S1'—C21—N4	10.0 (14)
C1—C2—C3	120.2 (2)	C17—C21—N4	113.6 (9)
C1—C2—H2	119.9	S1'—C21—H1B	117 (3)
C3—C2—H2	119.9	S1—C21—H1B	110 (2)
C12—C11—C10	119.4 (2)	C17—C21—H1B	139 (2)
C12—C11—H11	120.3	N4—C21—H1B	107 (2)
C10—C11—H11	120.3	C21—S1'—N4	164 (2)
N3—C5—C4	124.4 (2)	C21—S1'—C17	55.0 (13)
N3—C5—H5	117.8	N4—S1'—C17	140.4 (13)
C4—C5—H5	117.8	C21—S1'—C20	154.5 (16)
C11—C12—C7	122.0 (2)	N4—S1'—C20	40.9 (9)
C11—C12—H12	119.0	C17—S1'—C20	99.6 (5)
C7—C12—H12	119.0	C21—S1'—H1B	41.0 (19)
C15—C16—H16A	109.5	N4—S1'—H1B	123.6 (19)
C15—C16—H16B	109.5	C17—S1'—H1B	95.9 (16)
H16A—C16—H16B	109.5	C20—S1'—H1B	164.5 (16)
C15—C16—H16C	109.5	S1'—N4—C20	107.5 (13)
H16A—C16—H16C	109.5	S1'—N4—C21	5.5 (8)
H16B—C16—H16C	109.5	C20—N4—C21	113.0 (9)
C14—C13—H13A	109.5
O4—C8—C9—C10	−177.0 (2)	C17—S1—C20—C20^iii	179.7 (3)
C7—C8—C9—C10	2.5 (3)	N4—C20—C19—C18	1.8 (8)
O4—C8—C9—N2	2.8 (3)	C20^iii—C20—C19—C18	−179.7 (3)
C7—C8—C9—N2	−177.7 (2)	S1—C20—C19—C18	0.2 (4)
O3—N2—C9—C8	−85.8 (3)	S1'—C20—C19—C18	0.3 (4)
O2—N2—C9—C8	96.0 (2)	C20—C19—C18—C17	−0.1 (3)
O3—N2—C9—C10	94.0 (3)	C19—C18—C17—C21	1.1 (7)
O2—N2—C9—C10	−84.2 (3)	C19—C18—C17—S1'	−0.2 (4)
C8—C9—C10—O1	177.6 (2)	C19—C18—C17—S1	0.0 (3)
N2—C9—C10—O1	−2.3 (3)	C20—S1—C21—C17	2.3 (17)
C8—C9—C10—C11	−1.9 (3)	C18—C17—C21—S1'	−3.5 (19)
N2—C9—C10—C11	178.25 (19)	C18—C17—C21—S1	−2.1 (14)
C14—N1—C15—C14^i	−1.0 (3)	C18—C17—C21—N4	−2.9 (12)
C14—N1—C15—C16	177.87 (19)	S1'—C17—C21—N4	0.6 (13)
C15—N1—C14—C15^i	1.0 (3)	C17—C21—S1'—N4	177 (7)
C15—N1—C14—C13	−179.4 (2)	N4—C21—S1'—C17	−177 (7)
C4—C3—C6—C6^ii	0.6 (4)	C17—C21—S1'—C20	7 (4)
C2—C3—C6—C6^ii	−178.2 (3)	N4—C21—S1'—C20	−169 (11)
C5—N3—C1—C2	0.7 (3)	C18—C17—S1'—C21	177.1 (15)
O4—C8—C7—C12	178.2 (2)	C21—C17—S1'—N4	−179 (3)
C9—C8—C7—C12	−1.3 (3)	C18—C17—S1'—N4	−2 (2)
C2—C3—C4—C5	1.4 (3)	C21—C17—S1'—C20	−176.8 (18)
C6—C3—C4—C5	−177.4 (2)	C18—C17—S1'—C20	0.3 (4)
N3—C1—C2—C3	0.1 (3)	C21—S1'—N4—C20	−173 (7)
C4—C3—C2—C1	−1.2 (3)	C17—S1'—N4—C20	3 (3)
C6—C3—C2—C1	177.7 (2)	C17—S1'—N4—C21	176 (9)
O1—C10—C11—C12	−179.3 (2)	C20—S1'—N4—C21	173 (7)
C9—C10—C11—C12	0.1 (3)	C19—C20—N4—S1'	−2.8 (18)
C1—N3—C5—C4	−0.4 (3)	C20^iii—C20—N4—S1'	178.5 (11)
C3—C4—C5—N3	−0.7 (4)	C19—C20—N4—C21	−3.6 (14)
C10—C11—C12—C7	1.0 (4)	C20^iii—C20—N4—C21	177.7 (8)
C8—C7—C12—C11	−0.4 (4)	S1'—C20—N4—C21	−0.7 (7)
C21—S1—C20—C19	−1.5 (13)	C17—C21—N4—S1'	−3 (8)
C17—S1—C20—C19	−0.1 (4)	S1'—C21—N4—C20	7 (7)
C21—S1—C20—C20^iii	178.3 (11)	C17—C21—N4—C20	3.8 (14)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3, −y+2, −z; (iii) −x+2, −y+2, −z+1.

(26CRES-TMP)

Crystal data

C14H16Cl2N2O2	F(000) = 656
Mr = 315.19	Dx = 1.398 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
a = 9.302 (3) Å	Cell parameters from 3729 reflections
b = 9.394 (2) Å	θ = 2.2–27.5°
c = 17.660 (6) Å	µ = 0.44 mm^−1
β = 104.075 (16)°	T = 150 K
V = 1497.0 (8) Å^3	Prism, colorless
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	1828 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.151
profile data from ω–scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −12→12
Tmin = 0.613, Tmax = 1.000	k = −12→12
15055 measured reflections	l = −22→22
3400 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.079	H-atom parameters constrained
wR(F^2) = 0.339	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
3400 reflections	Δρmax = 1.63 e Å^−3
187 parameters	Δρmin = −1.58 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.52858 (14)	−0.11638 (13)	0.24050 (7)	0.0358 (4)
Cl2	1.08751 (13)	0.06257 (12)	0.37253 (7)	0.0355 (4)
O1	0.4420 (4)	0.1124 (3)	0.3340 (2)	0.0349 (9)
H1	0.421413	0.187826	0.352249	0.052*
O2	0.9414 (3)	0.2674 (4)	0.4518 (2)	0.0329 (8)
H2	0.897244	0.333702	0.466265	0.049*
N1	0.3674 (4)	0.3345 (4)	0.4217 (2)	0.0274 (8)
N2	0.2101 (4)	0.5320 (4)	0.4841 (2)	0.0280 (9)
C12	0.2528 (5)	0.4096 (5)	0.5218 (3)	0.0265 (10)
C13	0.3321 (5)	0.3089 (5)	0.4898 (3)	0.0289 (10)
C6	0.6893 (5)	0.1942 (5)	0.3933 (3)	0.0281 (10)
H6	0.652073	0.262907	0.421317	0.034*
C5	0.8432 (5)	0.1829 (4)	0.4028 (3)	0.0276 (10)
C4	0.8971 (5)	0.0766 (5)	0.3617 (3)	0.0276 (10)
C1	0.5910 (5)	0.1044 (5)	0.3427 (3)	0.0269 (10)
C3	0.8005 (5)	−0.0123 (4)	0.3111 (3)	0.0272 (10)
H3	0.837437	−0.081085	0.282939	0.033*
C2	0.6485 (5)	0.0009 (4)	0.3020 (3)	0.0279 (10)
C9	0.2467 (5)	0.5584 (4)	0.4171 (3)	0.0260 (10)
C8	0.3261 (5)	0.4584 (5)	0.3847 (3)	0.0269 (10)
C11	0.2102 (6)	0.3831 (5)	0.5972 (3)	0.0361 (12)
H11A	0.156628	0.463642	0.609485	0.054*
H11B	0.298005	0.368715	0.638190	0.054*
H11C	0.148808	0.299781	0.592164	0.054*
C10	0.1954 (6)	0.6975 (5)	0.3759 (3)	0.0369 (12)
H10A	0.121759	0.678620	0.328574	0.055*
H10B	0.278286	0.745189	0.363788	0.055*
H10C	0.153664	0.756832	0.409364	0.055*
C14	0.3817 (6)	0.1705 (5)	0.5297 (3)	0.0411 (13)
H14A	0.430699	0.114848	0.497862	0.062*
H14B	0.297150	0.119211	0.537486	0.062*
H14C	0.449008	0.188528	0.579304	0.062*
C7	0.3682 (6)	0.4853 (5)	0.3096 (3)	0.0368 (11)
H7A	0.429369	0.408784	0.299545	0.055*
H7B	0.421977	0.573250	0.313151	0.055*
H7C	0.280308	0.491193	0.267889	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0367 (8)	0.0308 (7)	0.0388 (8)	−0.0004 (5)	0.0068 (6)	−0.0107 (4)
Cl2	0.0291 (7)	0.0328 (8)	0.0468 (8)	0.0057 (5)	0.0134 (6)	−0.0050 (5)
O1	0.0299 (18)	0.0326 (19)	0.043 (2)	0.0016 (14)	0.0104 (16)	−0.0117 (15)
O2	0.0277 (17)	0.0285 (18)	0.0422 (19)	0.0029 (14)	0.0079 (15)	−0.0123 (14)
N1	0.0244 (18)	0.0238 (18)	0.035 (2)	0.0029 (15)	0.0089 (16)	−0.0012 (15)
N2	0.0264 (19)	0.0247 (19)	0.033 (2)	0.0003 (15)	0.0070 (16)	−0.0042 (15)
C12	0.024 (2)	0.029 (2)	0.027 (2)	0.0002 (18)	0.0074 (18)	−0.0059 (17)
C13	0.027 (2)	0.025 (2)	0.033 (2)	0.0033 (18)	0.0048 (19)	−0.0032 (17)
C6	0.031 (2)	0.024 (2)	0.031 (2)	0.0047 (18)	0.0125 (19)	−0.0068 (17)
C5	0.030 (2)	0.023 (2)	0.030 (2)	0.0042 (18)	0.0074 (19)	−0.0020 (17)
C4	0.029 (2)	0.024 (2)	0.032 (2)	0.0062 (18)	0.0121 (19)	−0.0009 (17)
C1	0.030 (2)	0.022 (2)	0.030 (2)	0.0035 (17)	0.0099 (19)	−0.0014 (17)
C3	0.033 (2)	0.021 (2)	0.030 (2)	0.0041 (18)	0.0130 (19)	−0.0041 (17)
C2	0.034 (2)	0.021 (2)	0.029 (2)	0.0003 (18)	0.0073 (19)	−0.0054 (16)
C9	0.023 (2)	0.023 (2)	0.030 (2)	−0.0022 (17)	0.0042 (18)	−0.0037 (16)
C8	0.021 (2)	0.026 (2)	0.032 (2)	−0.0003 (17)	0.0046 (18)	0.0008 (17)
C11	0.036 (3)	0.038 (3)	0.035 (3)	0.003 (2)	0.011 (2)	−0.003 (2)
C10	0.045 (3)	0.025 (2)	0.043 (3)	0.006 (2)	0.014 (2)	0.006 (2)
C14	0.051 (3)	0.034 (3)	0.041 (3)	0.019 (2)	0.018 (2)	0.007 (2)
C7	0.035 (3)	0.037 (3)	0.043 (3)	0.003 (2)	0.019 (2)	0.005 (2)

Geometric parameters (Å, º)

Cl1—C2	1.746 (5)	C1—C2	1.390 (6)
Cl2—C4	1.739 (5)	C3—C2	1.390 (6)
O1—C1	1.359 (6)	C3—H3	0.9300
O1—H1	0.8200	C9—C8	1.399 (6)
O2—C5	1.353 (5)	C9—C10	1.515 (6)
O2—H2	0.8200	C8—C7	1.493 (7)
N1—C13	1.344 (6)	C11—H11A	0.9600
N1—C8	1.344 (6)	C11—H11B	0.9600
N2—C9	1.332 (6)	C11—H11C	0.9600
N2—C12	1.339 (6)	C10—H10A	0.9600
C12—C13	1.400 (6)	C10—H10B	0.9600
C12—C11	1.499 (6)	C10—H10C	0.9600
C13—C14	1.497 (6)	C14—H14A	0.9600
C6—C1	1.396 (6)	C14—H14B	0.9600
C6—C5	1.404 (6)	C14—H14C	0.9600
C6—H6	0.9300	C7—H7A	0.9600
C5—C4	1.398 (6)	C7—H7B	0.9600
C4—C3	1.383 (6)	C7—H7C	0.9600
C1—O1—H1	109.5	N2—C9—C10	117.9 (4)
C5—O2—H2	109.5	C8—C9—C10	121.3 (4)
C13—N1—C8	119.1 (4)	N1—C8—C9	120.0 (4)
C9—N2—C12	119.5 (4)	N1—C8—C7	118.2 (4)
N2—C12—C13	120.0 (4)	C9—C8—C7	121.8 (4)
N2—C12—C11	118.3 (4)	C12—C11—H11A	109.5
C13—C12—C11	121.6 (4)	C12—C11—H11B	109.5
N1—C13—C12	120.5 (4)	H11A—C11—H11B	109.5
N1—C13—C14	117.5 (4)	C12—C11—H11C	109.5
C12—C13—C14	122.0 (4)	H11A—C11—H11C	109.5
C1—C6—C5	121.4 (4)	H11B—C11—H11C	109.5
C1—C6—H6	119.3	C9—C10—H10A	109.5
C5—C6—H6	119.3	C9—C10—H10B	109.5
O2—C5—C4	118.7 (4)	H10A—C10—H10B	109.5
O2—C5—C6	122.8 (4)	C9—C10—H10C	109.5
C4—C5—C6	118.5 (4)	H10A—C10—H10C	109.5
C3—C4—C5	120.5 (4)	H10B—C10—H10C	109.5
C3—C4—Cl2	120.6 (3)	C13—C14—H14A	109.5
C5—C4—Cl2	118.8 (4)	C13—C14—H14B	109.5
O1—C1—C2	119.3 (4)	H14A—C14—H14B	109.5
O1—C1—C6	122.0 (4)	C13—C14—H14C	109.5
C2—C1—C6	118.6 (4)	H14A—C14—H14C	109.5
C4—C3—C2	120.2 (4)	H14B—C14—H14C	109.5
C4—C3—H3	119.9	C8—C7—H7A	109.5
C2—C3—H3	119.9	C8—C7—H7B	109.5
C3—C2—C1	120.8 (4)	H7A—C7—H7B	109.5
C3—C2—Cl1	119.6 (3)	C8—C7—H7C	109.5
C1—C2—Cl1	119.7 (4)	H7A—C7—H7C	109.5
N2—C9—C8	120.8 (4)	H7B—C7—H7C	109.5

(27CRES-PHE)

Crystal data

C72H48Cl4N10O4	Z = 1
Mr = 1259.00	F(000) = 650
Triclinic, P1	Dx = 1.449 Mg m^−3
a = 10.807 (5) Å	Mo Kα radiation, λ = 0.71075 Å
b = 12.145 (5) Å	Cell parameters from 7173 reflections
c = 12.466 (6) Å	θ = 3.0–27.7°
α = 108.220 (8)°	µ = 0.27 mm^−1
β = 104.061 (7)°	T = 150 K
γ = 101.072 (7)°	Prism, colorless
V = 1442.3 (11) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3189 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.104
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −14→13
Tmin = 0.413, Tmax = 1.000	k = −15→15
11846 measured reflections	l = −16→16
6333 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.088	H-atom parameters constrained
wR(F^2) = 0.269	w = 1/[σ^2(Fo^2) + (0.1435P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
6333 reflections	Δρmax = 0.68 e Å^−3
408 parameters	Δρmin = −0.67 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl01	0.20780 (12)	−0.03104 (11)	0.94958 (10)	0.0367 (3)
Cl02	0.00215 (12)	0.34369 (11)	1.08446 (10)	0.0373 (4)
O2	0.0875 (3)	0.4082 (3)	0.9012 (3)	0.0371 (8)
H2	0.117313	0.425655	0.852210	0.056*
O1	0.2811 (3)	0.0814 (3)	0.7878 (3)	0.0391 (8)
H1	0.299973	0.115369	0.743980	0.059*
N3	0.3382 (4)	0.2067 (3)	0.6457 (3)	0.0288 (9)
N5	0.5352 (4)	0.0651 (3)	0.4295 (3)	0.0310 (9)
N1	0.1729 (4)	0.4791 (4)	0.7303 (3)	0.0300 (9)
N2	0.2504 (4)	0.5775 (4)	0.5690 (3)	0.0330 (9)
N4	0.4017 (4)	0.3300 (3)	0.4977 (3)	0.0300 (9)
C4	0.1097 (4)	0.1615 (4)	1.0051 (4)	0.0303 (11)
H4	0.084480	0.133461	1.060279	0.036*
C19	0.4272 (4)	0.3175 (4)	0.6922 (4)	0.0282 (10)
C7	0.2672 (4)	0.5875 (4)	0.7696 (4)	0.0312 (11)
C12	0.3050 (5)	0.6374 (4)	0.6882 (4)	0.0313 (11)
C2	0.1178 (4)	0.3093 (4)	0.9115 (4)	0.0303 (11)
C6	0.2161 (4)	0.1434 (4)	0.8543 (4)	0.0297 (10)
C34	0.4449 (4)	−0.0462 (4)	0.3798 (4)	0.0292 (10)
C20	0.4888 (4)	0.3741 (4)	0.8178 (4)	0.0317 (11)
H20	0.470152	0.334021	0.867157	0.038*
C1	0.1854 (4)	0.2451 (4)	0.8423 (4)	0.0311 (11)
H1A	0.210240	0.272338	0.786499	0.037*
C25	0.3126 (4)	0.2196 (4)	0.4517 (4)	0.0282 (10)
C14	0.0946 (5)	0.4038 (4)	0.4042 (4)	0.0342 (11)
H14	0.120403	0.434296	0.350740	0.041*
C33	0.5917 (4)	0.1117 (4)	0.5500 (4)	0.0296 (10)
C8	0.3297 (5)	0.6544 (4)	0.8945 (4)	0.0324 (11)
H8	0.306812	0.623307	0.948666	0.039*
C26	0.2500 (5)	0.1620 (5)	0.3257 (4)	0.0359 (12)
H26	0.272573	0.200565	0.276355	0.043*
C30	0.2769 (4)	0.1556 (4)	0.5252 (4)	0.0292 (10)
C24	0.4575 (4)	0.3795 (4)	0.6171 (4)	0.0302 (11)
C13	0.1572 (4)	0.4705 (4)	0.5298 (4)	0.0301 (10)
C18	0.1174 (5)	0.4202 (4)	0.6115 (4)	0.0306 (11)
C23	0.5509 (5)	0.4977 (4)	0.6709 (4)	0.0353 (11)
H23	0.572889	0.538429	0.623049	0.042*
C35	0.3822 (5)	−0.0987 (5)	0.2544 (4)	0.0370 (12)
H35	0.405556	−0.057980	0.206992	0.044*
C17	0.0160 (5)	0.3086 (4)	0.5634 (4)	0.0364 (12)
H17	−0.011629	0.275591	0.614594	0.044*
C5	0.1758 (4)	0.1003 (4)	0.9364 (4)	0.0301 (10)
C3	0.0803 (4)	0.2642 (4)	0.9932 (4)	0.0324 (11)
C21	0.5762 (5)	0.4884 (4)	0.8658 (4)	0.0341 (11)
H21	0.615744	0.525923	0.948190	0.041*
C15	−0.0014 (5)	0.2971 (5)	0.3621 (4)	0.0378 (12)
H15	−0.041243	0.254795	0.280259	0.045*
C32	0.6871 (5)	0.2280 (4)	0.6063 (4)	0.0373 (12)
H32	0.708354	0.272438	0.561282	0.045*
C29	0.1795 (5)	0.0418 (4)	0.4721 (4)	0.0363 (11)
H29	0.154675	0.001357	0.519275	0.044*
C16	−0.0416 (5)	0.2491 (5)	0.4437 (4)	0.0379 (12)
H16	−0.108372	0.175962	0.414034	0.045*
C11	0.4023 (5)	0.7524 (5)	0.7348 (4)	0.0364 (12)
H11	0.427097	0.786074	0.682931	0.044*
C9	0.4230 (5)	0.7641 (5)	0.9349 (4)	0.0376 (12)
H9	0.463336	0.806896	1.016689	0.045*
C31	0.7475 (5)	0.2740 (5)	0.7278 (5)	0.0409 (13)
H31	0.812263	0.348808	0.764881	0.049*
C36	0.2879 (5)	−0.2086 (5)	0.2030 (4)	0.0403 (13)
H36	0.246091	−0.241166	0.120751	0.048*
C28	0.1223 (5)	−0.0080 (5)	0.3520 (5)	0.0412 (13)
H28	0.058149	−0.083133	0.317398	0.049*
C22	0.6079 (5)	0.5512 (5)	0.7918 (4)	0.0422 (13)
H22	0.667480	0.628715	0.826263	0.051*
C10	0.4593 (5)	0.8135 (5)	0.8551 (4)	0.0403 (12)
H10	0.522861	0.888551	0.884694	0.048*
C27	0.1577 (5)	0.0514 (5)	0.2766 (4)	0.0425 (13)
H27	0.117608	0.014534	0.194237	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl01	0.0413 (7)	0.0289 (7)	0.0412 (7)	0.0082 (5)	0.0129 (5)	0.0165 (5)
Cl02	0.0419 (7)	0.0383 (8)	0.0313 (6)	0.0112 (6)	0.0164 (5)	0.0095 (5)
O2	0.047 (2)	0.034 (2)	0.0384 (19)	0.0148 (17)	0.0204 (15)	0.0177 (16)
O1	0.048 (2)	0.036 (2)	0.042 (2)	0.0167 (18)	0.0242 (16)	0.0170 (16)
N3	0.029 (2)	0.026 (2)	0.031 (2)	0.0065 (17)	0.0120 (16)	0.0093 (17)
N5	0.032 (2)	0.030 (2)	0.032 (2)	0.0082 (19)	0.0126 (17)	0.0112 (18)
N1	0.028 (2)	0.031 (2)	0.032 (2)	0.0091 (18)	0.0087 (16)	0.0141 (18)
N2	0.031 (2)	0.039 (3)	0.029 (2)	0.0111 (19)	0.0086 (16)	0.0121 (18)
N4	0.027 (2)	0.027 (2)	0.032 (2)	0.0018 (17)	0.0060 (16)	0.0122 (17)
C4	0.030 (3)	0.033 (3)	0.023 (2)	0.002 (2)	0.0072 (18)	0.009 (2)
C19	0.021 (2)	0.029 (3)	0.032 (2)	0.002 (2)	0.0092 (18)	0.011 (2)
C7	0.028 (3)	0.033 (3)	0.035 (2)	0.009 (2)	0.0136 (19)	0.012 (2)
C12	0.031 (3)	0.027 (3)	0.032 (2)	0.004 (2)	0.0093 (19)	0.011 (2)
C2	0.024 (2)	0.029 (3)	0.030 (2)	0.000 (2)	0.0016 (18)	0.011 (2)
C6	0.029 (3)	0.031 (3)	0.030 (2)	0.007 (2)	0.0109 (18)	0.013 (2)
C34	0.026 (3)	0.028 (3)	0.029 (2)	0.006 (2)	0.0082 (18)	0.007 (2)
C20	0.030 (3)	0.032 (3)	0.032 (2)	0.005 (2)	0.0106 (19)	0.012 (2)
C1	0.032 (3)	0.034 (3)	0.028 (2)	0.008 (2)	0.0101 (19)	0.013 (2)
C25	0.025 (2)	0.025 (3)	0.028 (2)	0.003 (2)	0.0044 (18)	0.0068 (19)
C14	0.034 (3)	0.035 (3)	0.032 (2)	0.010 (2)	0.008 (2)	0.012 (2)
C33	0.029 (3)	0.030 (3)	0.031 (2)	0.012 (2)	0.0133 (19)	0.010 (2)
C8	0.043 (3)	0.029 (3)	0.030 (2)	0.012 (2)	0.015 (2)	0.013 (2)
C26	0.032 (3)	0.035 (3)	0.035 (3)	0.010 (2)	0.005 (2)	0.011 (2)
C30	0.026 (2)	0.027 (3)	0.036 (2)	0.007 (2)	0.0131 (19)	0.011 (2)
C24	0.025 (2)	0.030 (3)	0.027 (2)	0.002 (2)	0.0036 (18)	0.007 (2)
C13	0.025 (3)	0.030 (3)	0.035 (2)	0.010 (2)	0.0078 (19)	0.014 (2)
C18	0.033 (3)	0.028 (3)	0.037 (3)	0.014 (2)	0.016 (2)	0.014 (2)
C23	0.031 (3)	0.031 (3)	0.033 (2)	−0.002 (2)	0.0017 (19)	0.011 (2)
C35	0.040 (3)	0.041 (3)	0.030 (2)	0.013 (3)	0.012 (2)	0.012 (2)
C17	0.035 (3)	0.031 (3)	0.042 (3)	0.005 (2)	0.009 (2)	0.017 (2)
C5	0.029 (3)	0.030 (3)	0.025 (2)	0.003 (2)	0.0053 (18)	0.008 (2)
C3	0.030 (3)	0.032 (3)	0.026 (2)	0.005 (2)	0.0054 (18)	0.005 (2)
C21	0.032 (3)	0.032 (3)	0.024 (2)	0.005 (2)	0.0006 (18)	0.002 (2)
C15	0.041 (3)	0.032 (3)	0.037 (3)	0.011 (2)	0.010 (2)	0.011 (2)
C32	0.038 (3)	0.027 (3)	0.052 (3)	0.009 (2)	0.022 (2)	0.016 (2)
C29	0.036 (3)	0.024 (3)	0.047 (3)	0.006 (2)	0.012 (2)	0.015 (2)
C16	0.032 (3)	0.035 (3)	0.041 (3)	0.008 (2)	0.007 (2)	0.012 (2)
C11	0.037 (3)	0.034 (3)	0.036 (3)	0.005 (2)	0.010 (2)	0.015 (2)
C9	0.043 (3)	0.030 (3)	0.033 (2)	0.009 (2)	0.009 (2)	0.006 (2)
C31	0.031 (3)	0.030 (3)	0.050 (3)	0.002 (2)	0.015 (2)	0.003 (2)
C36	0.037 (3)	0.050 (4)	0.029 (2)	0.019 (3)	0.007 (2)	0.008 (2)
C28	0.028 (3)	0.026 (3)	0.055 (3)	0.002 (2)	0.003 (2)	0.009 (2)
C22	0.036 (3)	0.028 (3)	0.048 (3)	0.001 (2)	0.000 (2)	0.010 (2)
C10	0.037 (3)	0.032 (3)	0.044 (3)	0.003 (2)	0.006 (2)	0.012 (2)
C27	0.047 (3)	0.038 (3)	0.036 (3)	0.011 (3)	0.005 (2)	0.012 (2)

Geometric parameters (Å, º)

Cl01—C5	1.743 (5)	C14—H14	0.9300
Cl02—C3	1.741 (5)	C33—C32	1.420 (7)
O2—C2	1.338 (5)	C8—C9	1.365 (7)
O2—H2	0.8200	C8—H8	0.9300
O1—C6	1.358 (5)	C26—C27	1.360 (7)
O1—H1	0.8200	C26—H26	0.9300
N3—C19	1.347 (6)	C30—C29	1.410 (6)
N3—C30	1.363 (5)	C24—C23	1.429 (6)
N5—C34	1.356 (6)	C13—C18	1.448 (6)
N5—C33	1.357 (5)	C18—C17	1.414 (7)
N1—C18	1.344 (6)	C23—C22	1.363 (6)
N1—C7	1.361 (6)	C23—H23	0.9300
N2—C13	1.343 (6)	C35—C36	1.363 (7)
N2—C12	1.348 (5)	C35—H35	0.9300
N4—C24	1.344 (5)	C17—C16	1.356 (6)
N4—C25	1.345 (6)	C17—H17	0.9300
C4—C5	1.378 (6)	C21—C22	1.429 (7)
C4—C3	1.387 (6)	C21—H21	0.9300
C4—H4	0.9300	C15—C16	1.431 (7)
C19—C20	1.419 (6)	C15—H15	0.9300
C19—C24	1.431 (6)	C32—C31	1.372 (7)
C7—C8	1.424 (6)	C32—H32	0.9300
C7—C12	1.433 (6)	C29—C28	1.354 (7)
C12—C11	1.423 (7)	C29—H29	0.9300
C2—C3	1.403 (6)	C16—H16	0.9300
C2—C1	1.410 (6)	C11—C10	1.364 (6)
C6—C1	1.381 (6)	C11—H11	0.9300
C6—C5	1.406 (6)	C9—C10	1.405 (7)
C34—C35	1.416 (6)	C9—H9	0.9300
C34—C33^i	1.428 (6)	C31—C36^i	1.412 (7)
C20—C21	1.372 (7)	C31—H31	0.9300
C20—H20	0.9300	C36—H36	0.9300
C1—H1A	0.9300	C28—C27	1.428 (7)
C25—C26	1.425 (6)	C28—H28	0.9300
C25—C30	1.446 (6)	C22—H22	0.9300
C14—C15	1.351 (7)	C10—H10	0.9300
C14—C13	1.430 (6)	C27—H27	0.9300
C2—O2—H2	109.5	N1—C18—C17	120.5 (4)
C6—O1—H1	109.5	N1—C18—C13	121.1 (4)
C19—N3—C30	118.2 (4)	C17—C18—C13	118.4 (4)
C34—N5—C33	117.0 (4)	C22—C23—C24	120.5 (5)
C18—N1—C7	116.9 (4)	C22—C23—H23	119.8
C13—N2—C12	117.3 (4)	C24—C23—H23	119.8
C24—N4—C25	116.6 (4)	C36—C35—C34	120.3 (5)
C5—C4—C3	121.0 (4)	C36—C35—H35	119.9
C5—C4—H4	119.5	C34—C35—H35	119.9
C3—C4—H4	119.5	C16—C17—C18	121.0 (5)
N3—C19—C20	119.1 (4)	C16—C17—H17	119.5
N3—C19—C24	121.0 (4)	C18—C17—H17	119.5
C20—C19—C24	119.9 (4)	C4—C5—C6	119.7 (4)
N1—C7—C8	119.7 (4)	C4—C5—Cl01	120.3 (4)
N1—C7—C12	121.6 (4)	C6—C5—Cl01	120.0 (4)
C8—C7—C12	118.7 (4)	C4—C3—C2	120.9 (4)
N2—C12—C11	119.7 (4)	C4—C3—Cl02	120.5 (4)
N2—C12—C7	121.3 (4)	C2—C3—Cl02	118.5 (4)
C11—C12—C7	119.0 (4)	C20—C21—C22	121.4 (4)
O2—C2—C3	119.8 (4)	C20—C21—H21	119.3
O2—C2—C1	123.3 (4)	C22—C21—H21	119.3
C3—C2—C1	117.0 (4)	C14—C15—C16	120.0 (5)
O1—C6—C1	122.6 (4)	C14—C15—H15	120.0
O1—C6—C5	118.5 (4)	C16—C15—H15	120.0
C1—C6—C5	118.9 (4)	C31—C32—C33	119.4 (5)
N5—C34—C35	119.3 (4)	C31—C32—H32	120.3
N5—C34—C33^i	122.2 (4)	C33—C32—H32	120.3
C35—C34—C33^i	118.5 (4)	C28—C29—C30	119.4 (5)
C21—C20—C19	119.3 (4)	C28—C29—H29	120.3
C21—C20—H20	120.3	C30—C29—H29	120.3
C19—C20—H20	120.3	C17—C16—C15	121.0 (5)
C6—C1—C2	122.5 (4)	C17—C16—H16	119.5
C6—C1—H1A	118.8	C15—C16—H16	119.5
C2—C1—H1A	118.8	C10—C11—C12	120.4 (5)
N4—C25—C26	119.3 (4)	C10—C11—H11	119.8
N4—C25—C30	122.7 (4)	C12—C11—H11	119.8
C26—C25—C30	118.0 (4)	C8—C9—C10	121.1 (4)
C15—C14—C13	121.0 (4)	C8—C9—H9	119.4
C15—C14—H14	119.5	C10—C9—H9	119.4
C13—C14—H14	119.5	C32—C31—C36^i	120.5 (5)
N5—C33—C32	119.1 (4)	C32—C31—H31	119.8
N5—C33—C34^i	120.8 (4)	C36^i—C31—H31	119.8
C32—C33—C34^i	120.0 (4)	C35—C36—C31^i	121.3 (4)
C9—C8—C7	120.2 (4)	C35—C36—H36	119.4
C9—C8—H8	119.9	C31^i—C36—H36	119.4
C7—C8—H8	119.9	C29—C28—C27	121.9 (5)
C27—C26—C25	120.7 (5)	C29—C28—H28	119.0
C27—C26—H26	119.6	C27—C28—H28	119.0
C25—C26—H26	119.6	C23—C22—C21	120.1 (5)
N3—C30—C29	120.6 (4)	C23—C22—H22	120.0
N3—C30—C25	119.3 (4)	C21—C22—H22	120.0
C29—C30—C25	120.1 (4)	C11—C10—C9	120.6 (5)
N4—C24—C23	119.0 (4)	C11—C10—H10	119.7
N4—C24—C19	122.2 (4)	C9—C10—H10	119.7
C23—C24—C19	118.8 (4)	C26—C27—C28	119.9 (5)
N2—C13—C14	119.7 (4)	C26—C27—H27	120.1
N2—C13—C18	121.7 (4)	C28—C27—H27	120.1
C14—C13—C18	118.6 (4)

Symmetry code: (i) −x+1, −y, −z+1.

(28CRES-DMP)

Crystal data

C12H12Cl2N2O2	F(000) = 592
Mr = 287.14	Dx = 1.406 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 8.188 (12) Å	Cell parameters from 3075 reflections
b = 15.73 (2) Å	θ = 3.2–27.5°
c = 11.247 (16) Å	µ = 0.47 mm^−1
β = 110.491 (16)°	T = 150 K
V = 1357 (3) Å^3	Block, colorless
Z = 4	0.41 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2111 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.115
profile data from ω–scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −10→10
Tmin = 0.950, Tmax = 1.000	k = −20→20
7471 measured reflections	l = −12→14
3075 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.206	w = 1/[σ^2(Fo^2) + (0.1001P)^2 + 0.2332P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3075 reflections	Δρmax = 0.29 e Å^−3
167 parameters	Δρmin = −0.40 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl01	1.09648 (11)	0.69449 (6)	0.75323 (10)	0.0749 (3)
Cl02	0.58993 (13)	0.71985 (7)	0.29686 (9)	0.0774 (4)
O1	0.8356 (3)	0.59886 (16)	0.8224 (2)	0.0651 (6)
H1	0.753466	0.587013	0.845110	0.098*
O2	0.3852 (3)	0.62137 (17)	0.4089 (2)	0.0694 (7)
H2	0.326541	0.597031	0.444489	0.104*
N2	0.1360 (3)	0.54121 (16)	0.4782 (3)	0.0532 (6)
N1	0.5952 (4)	0.5317 (2)	0.9295 (3)	0.0687 (8)
C007	0.5471 (3)	0.63644 (17)	0.4938 (3)	0.0462 (6)
C1	0.6066 (3)	0.60794 (18)	0.6177 (3)	0.0492 (7)
H1A	0.532392	0.576151	0.646760	0.059*
C2	0.7741 (3)	0.62546 (17)	0.7000 (3)	0.0463 (6)
C4	0.8289 (4)	0.70046 (17)	0.5320 (3)	0.0511 (7)
H4	0.903713	0.731617	0.502717	0.061*
C5	0.6612 (4)	0.68367 (18)	0.4516 (3)	0.0479 (6)
C7	−0.0218 (4)	0.5365 (2)	0.3857 (3)	0.0523 (7)
C3	0.8862 (4)	0.67152 (17)	0.6549 (3)	0.0495 (7)
C10	0.6135 (4)	0.4497 (2)	0.9665 (3)	0.0630 (9)
C8	0.1541 (4)	0.50547 (19)	0.5892 (3)	0.0550 (7)
H8	0.262369	0.508976	0.653787	0.066*
C11	0.4842 (4)	0.5799 (3)	0.9625 (3)	0.0700 (9)
H11	0.471294	0.636453	0.936788	0.084*
C9	0.7407 (5)	0.3957 (3)	0.9327 (4)	0.0833 (12)
H9A	0.717136	0.399152	0.843048	0.125*
H9B	0.729705	0.337703	0.955653	0.125*
H9C	0.856969	0.415341	0.977796	0.125*
C6	−0.0478 (5)	0.5743 (3)	0.2602 (4)	0.0769 (10)
H6A	0.044082	0.614208	0.267707	0.115*
H6B	−0.158069	0.603112	0.229773	0.115*
H6C	−0.046107	0.530262	0.201581	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl01	0.0432 (5)	0.0904 (7)	0.0771 (6)	−0.0169 (4)	0.0035 (4)	0.0048 (5)
Cl02	0.0720 (6)	0.1006 (7)	0.0555 (5)	−0.0257 (5)	0.0173 (4)	0.0152 (4)
O1	0.0452 (11)	0.0896 (16)	0.0557 (13)	−0.0021 (11)	0.0118 (10)	0.0187 (12)
O2	0.0457 (11)	0.1025 (19)	0.0541 (13)	−0.0255 (12)	0.0100 (10)	0.0113 (12)
N2	0.0397 (12)	0.0565 (14)	0.0656 (16)	−0.0104 (11)	0.0211 (11)	−0.0074 (12)
N1	0.0520 (15)	0.107 (2)	0.0430 (14)	−0.0165 (16)	0.0119 (12)	0.0154 (15)
C007	0.0352 (13)	0.0503 (15)	0.0513 (16)	−0.0060 (11)	0.0131 (11)	−0.0006 (12)
C1	0.0387 (13)	0.0541 (16)	0.0580 (17)	−0.0060 (12)	0.0211 (13)	0.0066 (13)
C2	0.0382 (13)	0.0493 (15)	0.0509 (15)	0.0008 (11)	0.0150 (11)	0.0031 (12)
C4	0.0450 (15)	0.0500 (15)	0.0620 (18)	−0.0129 (12)	0.0232 (14)	−0.0012 (13)
C5	0.0450 (15)	0.0492 (15)	0.0492 (16)	−0.0051 (12)	0.0161 (12)	0.0037 (12)
C7	0.0411 (14)	0.0565 (16)	0.0612 (18)	−0.0035 (13)	0.0203 (13)	−0.0065 (14)
C3	0.0384 (14)	0.0476 (14)	0.0601 (17)	−0.0024 (11)	0.0142 (12)	−0.0018 (13)
C10	0.0472 (16)	0.098 (3)	0.0356 (15)	−0.0112 (16)	0.0041 (12)	0.0067 (15)
C8	0.0395 (14)	0.0644 (18)	0.0597 (18)	−0.0097 (13)	0.0158 (13)	−0.0087 (14)
C11	0.0543 (18)	0.098 (3)	0.0543 (19)	−0.0105 (18)	0.0148 (15)	0.0184 (18)
C9	0.063 (2)	0.126 (3)	0.055 (2)	−0.003 (2)	0.0142 (17)	0.000 (2)
C6	0.060 (2)	0.098 (3)	0.070 (2)	−0.0089 (19)	0.0197 (18)	0.008 (2)

Geometric parameters (Å, º)

Cl01—C3	1.727 (4)	C4—C3	1.373 (5)
Cl02—C5	1.727 (4)	C4—C5	1.380 (4)
O1—C2	1.356 (4)	C4—H4	0.9300
O1—H1	0.8200	C7—C8^i	1.379 (4)
O2—C007	1.356 (4)	C7—C6	1.477 (5)
O2—H2	0.8200	C10—C11^ii	1.393 (4)
N2—C8	1.330 (4)	C10—C9	1.492 (5)
N2—C7	1.347 (4)	C8—H8	0.9300
N1—C11	1.332 (5)	C11—H11	0.9300
N1—C10	1.347 (5)	C9—H9A	0.9600
C007—C1	1.380 (5)	C9—H9B	0.9600
C007—C5	1.400 (4)	C9—H9C	0.9600
C1—C2	1.388 (4)	C6—H6A	0.9600
C1—H1A	0.9300	C6—H6B	0.9600
C2—C3	1.397 (4)	C6—H6C	0.9600
C2—O1—H1	109.5	C4—C3—Cl01	119.2 (2)
C007—O2—H2	109.5	C2—C3—Cl01	120.7 (3)
C8—N2—C7	117.6 (2)	N1—C10—C11^ii	118.2 (3)
C11—N1—C10	118.2 (3)	N1—C10—C9	118.6 (3)
O2—C007—C1	124.5 (2)	C11^ii—C10—C9	123.2 (4)
O2—C007—C5	117.3 (3)	N2—C8—C7^i	123.8 (3)
C1—C007—C5	118.3 (3)	N2—C8—H8	118.1
C007—C1—C2	121.7 (2)	C7^i—C8—H8	118.1
C007—C1—H1A	119.1	N1—C11—C10^ii	123.6 (4)
C2—C1—H1A	119.1	N1—C11—H11	118.2
O1—C2—C1	123.0 (2)	C10^ii—C11—H11	118.2
O1—C2—C3	118.1 (3)	C10—C9—H9A	109.5
C1—C2—C3	118.9 (3)	C10—C9—H9B	109.5
C3—C4—C5	120.5 (3)	H9A—C9—H9B	109.5
C3—C4—H4	119.7	C10—C9—H9C	109.5
C5—C4—H4	119.7	H9A—C9—H9C	109.5
C4—C5—C007	120.6 (3)	H9B—C9—H9C	109.5
C4—C5—Cl02	120.4 (2)	C7—C6—H6A	109.5
C007—C5—Cl02	119.1 (2)	C7—C6—H6B	109.5
N2—C7—C8^i	118.6 (3)	H6A—C6—H6B	109.5
N2—C7—C6	119.6 (3)	C7—C6—H6C	109.5
C8^i—C7—C6	121.9 (3)	H6A—C6—H6C	109.5
C4—C3—C2	120.1 (3)	H6B—C6—H6C	109.5

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+2.

(29CRES-TMP-PYR)

Crystal data

C44H42Cl4N4O4	F(000) = 3472
Mr = 832.61	Dx = 1.390 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 42.727 (11) Å	Cell parameters from 10775 reflections
b = 8.899 (3) Å	θ = 3.1–28.2°
c = 22.920 (6) Å	µ = 0.35 mm^−1
β = 114.062 (8)°	T = 150 K
V = 7958 (4) Å^3	Block, colorless
Z = 8	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	5937 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.082
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	θmax = 27.5°, θmin = 3.0°
Tmin = 0.797, Tmax = 1.000	h = −55→55
37117 measured reflections	k = −11→11
9097 independent reflections	l = −29→29

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0471P)^2 + 0.8588P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
9097 reflections	Δρmax = 0.28 e Å^−3
517 parameters	Δρmin = −0.35 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C29	0.09173 (6)	0.2370 (3)	0.36649 (11)	0.0269 (6)
C30	0.08913 (6)	0.3890 (3)	0.38485 (13)	0.0343 (6)
H30	0.079142	0.461347	0.353435	0.041*
C31	0.10096 (6)	0.4288 (3)	0.44715 (13)	0.0316 (6)
H31	0.098996	0.528335	0.457519	0.038*
C32	0.11633 (6)	0.3228 (3)	0.49729 (12)	0.0253 (6)
C33	0.12849 (6)	0.3615 (3)	0.56164 (12)	0.0312 (6)
H33	0.127174	0.460726	0.573128	0.037*
C34	0.14252 (6)	0.2536 (3)	0.60868 (12)	0.0329 (6)
H34	0.150522	0.281509	0.651416	0.039*
C35	0.14484 (6)	0.1055 (3)	0.59323 (12)	0.0299 (6)
H35	0.154243	0.034722	0.625572	0.036*
C36	0.13328 (6)	0.0611 (3)	0.52987 (11)	0.0232 (5)
C37	0.13551 (6)	−0.0909 (3)	0.51095 (12)	0.0303 (6)
H37	0.144685	−0.164048	0.542321	0.036*
C38	0.12486 (6)	−0.1301 (3)	0.44991 (13)	0.0310 (6)
H38	0.127289	−0.229423	0.439828	0.037*
C39	0.10966 (6)	−0.0232 (3)	0.39903 (12)	0.0251 (6)
C40	0.09821 (6)	−0.0621 (3)	0.33507 (12)	0.0336 (6)
H40	0.100254	−0.160882	0.323901	0.040*
C41	0.08376 (7)	0.0446 (3)	0.28765 (13)	0.0380 (7)
H41	0.076197	0.016612	0.244993	0.046*
C42	0.08046 (6)	0.1909 (3)	0.30285 (12)	0.0361 (7)
H42	0.070568	0.260773	0.270282	0.043*
C43	0.10672 (6)	0.1286 (3)	0.41530 (11)	0.0220 (5)
C44	0.11881 (6)	0.1708 (3)	0.48079 (11)	0.0208 (5)
Cl1	0.03900 (2)	0.65258 (7)	0.23691 (3)	0.03210 (17)
Cl2	0.14923 (2)	0.43438 (7)	0.20717 (3)	0.02848 (16)
O1	0.00136 (4)	0.43055 (18)	0.14016 (8)	0.0282 (4)
H1	−0.007847	0.358648	0.117197	0.042*
O2	0.09899 (4)	0.25334 (19)	0.10676 (8)	0.0311 (4)
H2	0.084268	0.200532	0.080357	0.047*
C7	0.03513 (6)	0.4303 (3)	0.15345 (11)	0.0213 (5)
C8	0.05657 (6)	0.5309 (2)	0.19928 (11)	0.0215 (5)
C9	0.09145 (6)	0.5321 (3)	0.21555 (11)	0.0226 (5)
H9	0.105508	0.597566	0.246905	0.027*
C10	0.10547 (6)	0.4363 (3)	0.18543 (11)	0.0208 (5)
C11	0.08457 (6)	0.3390 (3)	0.13742 (11)	0.0213 (5)
C12	0.04976 (6)	0.3368 (2)	0.12312 (11)	0.0218 (5)
H12	0.035769	0.270344	0.092152	0.026*
Cl3	0.21849 (2)	0.27185 (8)	0.21401 (3)	0.03723 (18)
Cl4	0.34675 (2)	0.38423 (7)	0.23559 (3)	0.03100 (16)
O3	0.21856 (4)	0.0435 (2)	0.12444 (9)	0.0354 (5)
H3	0.218830	−0.015829	0.097258	0.053*
O4	0.33236 (4)	0.14334 (19)	0.14121 (8)	0.0281 (4)
H4	0.327330	0.075155	0.114900	0.042*
C1	0.30574 (6)	0.1698 (3)	0.15749 (11)	0.0219 (5)
C2	0.30896 (6)	0.2820 (3)	0.20209 (10)	0.0222 (5)
C3	0.28254 (6)	0.3125 (3)	0.22007 (11)	0.0246 (5)
H3A	0.285008	0.387214	0.250013	0.029*
C4	0.25243 (6)	0.2321 (3)	0.19353 (11)	0.0243 (5)
C5	0.24852 (6)	0.1187 (3)	0.14911 (11)	0.0244 (5)
C6	0.27521 (6)	0.0902 (3)	0.13169 (11)	0.0251 (6)
H6	0.272694	0.015482	0.101738	0.030*
N1	0.02741 (5)	0.1845 (2)	0.43765 (9)	0.0215 (4)
N2	0.05231 (5)	−0.0574 (2)	0.51781 (9)	0.0227 (4)
C13	0.01265 (6)	0.0319 (3)	0.34227 (11)	0.0306 (6)
H13A	0.003709	0.127034	0.322942	0.046*
H13B	−0.005430	−0.041314	0.328798	0.046*
H13C	0.030365	0.000092	0.329407	0.046*
C14	0.02715 (5)	0.0470 (3)	0.41337 (11)	0.0207 (5)
C15	0.04012 (6)	−0.0754 (3)	0.45442 (11)	0.0213 (5)
C16	0.04063 (7)	−0.2311 (3)	0.42960 (12)	0.0328 (6)
H16A	0.050655	−0.299105	0.464885	0.049*
H16B	0.053930	−0.231377	0.404481	0.049*
H16C	0.017613	−0.262295	0.403569	0.049*
C17	0.06461 (7)	0.0940 (3)	0.61296 (11)	0.0346 (6)
H17A	0.046123	0.124887	0.623803	0.052*
H17B	0.082625	0.167400	0.628199	0.052*
H17C	0.073248	−0.001372	0.632454	0.052*
C18	0.05186 (6)	0.0801 (3)	0.54168 (11)	0.0226 (5)
C19	0.03936 (6)	0.2023 (3)	0.50104 (11)	0.0211 (5)
C20	0.03843 (7)	0.3573 (3)	0.52550 (12)	0.0324 (6)
H20A	0.033111	0.428254	0.491226	0.049*
H20B	0.060373	0.381025	0.558728	0.049*
H20C	0.021192	0.362169	0.542236	0.049*
N3	0.18702 (5)	0.4077 (2)	0.44886 (9)	0.0248 (5)
N4	0.21437 (5)	0.1804 (2)	0.53673 (9)	0.0256 (5)
C21	0.17497 (7)	0.2388 (3)	0.35900 (12)	0.0369 (7)
H21A	0.164118	0.328350	0.336497	0.055*
H21B	0.158549	0.158469	0.347685	0.055*
H21C	0.193508	0.211744	0.347625	0.055*
C22	0.18857 (6)	0.2664 (3)	0.42941 (11)	0.0240 (5)
C23	0.20276 (6)	0.1522 (3)	0.47414 (11)	0.0245 (5)
C24	0.20581 (7)	−0.0055 (3)	0.45395 (13)	0.0353 (6)
H24A	0.220892	−0.007056	0.432322	0.053*
H24B	0.183597	−0.041435	0.425653	0.053*
H24C	0.214900	−0.069097	0.490964	0.053*
C25	0.22639 (7)	0.3500 (3)	0.62686 (12)	0.0399 (7)
H25A	0.234335	0.257294	0.649535	0.060*
H25B	0.208581	0.391155	0.637389	0.060*
H25C	0.245081	0.419908	0.638800	0.060*
C26	0.21262 (6)	0.3212 (3)	0.55635 (11)	0.0251 (5)
C27	0.19902 (6)	0.4361 (3)	0.51159 (11)	0.0236 (5)
C28	0.19736 (7)	0.5950 (3)	0.53174 (13)	0.0376 (7)
H28A	0.220099	0.630365	0.557233	0.056*
H28B	0.183800	0.599157	0.556358	0.056*
H28C	0.187102	0.657329	0.494552	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C29	0.0234 (13)	0.0326 (15)	0.0236 (14)	−0.0004 (11)	0.0086 (11)	0.0055 (11)
C30	0.0313 (15)	0.0309 (16)	0.0366 (16)	0.0034 (12)	0.0096 (13)	0.0135 (12)
C31	0.0344 (15)	0.0196 (14)	0.0436 (17)	0.0047 (12)	0.0187 (13)	0.0054 (12)
C32	0.0229 (13)	0.0258 (14)	0.0282 (14)	0.0027 (11)	0.0116 (11)	0.0019 (11)
C33	0.0329 (15)	0.0291 (15)	0.0348 (16)	0.0000 (12)	0.0171 (13)	−0.0064 (12)
C34	0.0352 (15)	0.0394 (17)	0.0235 (14)	−0.0027 (13)	0.0113 (12)	−0.0047 (12)
C35	0.0288 (14)	0.0366 (16)	0.0225 (14)	0.0029 (12)	0.0087 (11)	0.0057 (11)
C36	0.0190 (12)	0.0261 (14)	0.0265 (14)	0.0016 (11)	0.0111 (11)	0.0035 (11)
C37	0.0261 (14)	0.0268 (15)	0.0382 (16)	0.0067 (12)	0.0134 (12)	0.0077 (12)
C38	0.0291 (14)	0.0224 (14)	0.0430 (17)	0.0044 (11)	0.0162 (13)	−0.0012 (12)
C39	0.0196 (13)	0.0281 (14)	0.0283 (14)	−0.0015 (11)	0.0107 (11)	−0.0037 (11)
C40	0.0279 (14)	0.0389 (17)	0.0339 (16)	−0.0065 (13)	0.0125 (13)	−0.0142 (13)
C41	0.0316 (15)	0.057 (2)	0.0262 (15)	−0.0152 (14)	0.0121 (13)	−0.0138 (14)
C42	0.0290 (15)	0.0503 (19)	0.0250 (15)	−0.0046 (14)	0.0068 (12)	0.0104 (13)
C43	0.0157 (12)	0.0289 (14)	0.0221 (13)	−0.0033 (10)	0.0085 (10)	0.0000 (10)
C44	0.0166 (12)	0.0241 (13)	0.0226 (13)	−0.0016 (10)	0.0090 (10)	0.0002 (10)
Cl1	0.0299 (3)	0.0296 (4)	0.0336 (4)	0.0010 (3)	0.0097 (3)	−0.0127 (3)
Cl2	0.0201 (3)	0.0344 (4)	0.0266 (3)	−0.0016 (3)	0.0051 (3)	0.0004 (3)
O1	0.0206 (9)	0.0241 (10)	0.0357 (11)	−0.0052 (8)	0.0072 (8)	−0.0114 (8)
O2	0.0259 (9)	0.0325 (11)	0.0348 (11)	−0.0045 (8)	0.0124 (8)	−0.0164 (8)
C7	0.0211 (12)	0.0176 (12)	0.0232 (13)	−0.0002 (10)	0.0069 (10)	0.0011 (10)
C8	0.0257 (13)	0.0164 (12)	0.0205 (13)	0.0002 (10)	0.0076 (11)	−0.0010 (10)
C9	0.0257 (13)	0.0214 (13)	0.0164 (12)	−0.0073 (10)	0.0043 (10)	−0.0023 (10)
C10	0.0189 (12)	0.0210 (13)	0.0198 (12)	−0.0028 (10)	0.0052 (10)	0.0026 (10)
C11	0.0239 (13)	0.0168 (13)	0.0218 (13)	0.0001 (10)	0.0077 (11)	−0.0011 (10)
C12	0.0238 (13)	0.0173 (12)	0.0201 (13)	−0.0054 (10)	0.0045 (10)	−0.0046 (10)
Cl3	0.0295 (4)	0.0488 (4)	0.0352 (4)	0.0070 (3)	0.0151 (3)	−0.0070 (3)
Cl4	0.0318 (3)	0.0308 (4)	0.0277 (3)	−0.0097 (3)	0.0093 (3)	−0.0052 (3)
O3	0.0232 (9)	0.0392 (12)	0.0415 (12)	−0.0050 (9)	0.0108 (8)	−0.0186 (9)
O4	0.0269 (9)	0.0302 (11)	0.0284 (10)	−0.0041 (8)	0.0125 (8)	−0.0102 (8)
C1	0.0239 (13)	0.0211 (13)	0.0190 (13)	0.0036 (11)	0.0070 (10)	0.0019 (10)
C2	0.0222 (13)	0.0217 (13)	0.0170 (12)	−0.0028 (10)	0.0024 (10)	0.0004 (10)
C3	0.0299 (14)	0.0235 (13)	0.0155 (12)	0.0056 (11)	0.0043 (11)	0.0004 (10)
C4	0.0236 (13)	0.0257 (14)	0.0216 (13)	0.0071 (11)	0.0071 (11)	0.0002 (10)
C5	0.0213 (13)	0.0242 (14)	0.0228 (13)	0.0004 (11)	0.0040 (11)	−0.0013 (10)
C6	0.0249 (13)	0.0253 (14)	0.0215 (13)	0.0019 (11)	0.0057 (11)	−0.0065 (10)
N1	0.0168 (10)	0.0214 (11)	0.0259 (11)	0.0021 (8)	0.0084 (9)	0.0032 (9)
N2	0.0238 (11)	0.0194 (11)	0.0248 (11)	0.0021 (9)	0.0100 (9)	0.0039 (9)
C13	0.0284 (14)	0.0317 (15)	0.0271 (14)	−0.0012 (12)	0.0065 (12)	0.0001 (11)
C14	0.0158 (12)	0.0226 (13)	0.0227 (13)	−0.0017 (10)	0.0068 (10)	0.0007 (10)
C15	0.0188 (12)	0.0192 (13)	0.0260 (14)	−0.0016 (10)	0.0094 (10)	−0.0006 (10)
C16	0.0365 (15)	0.0233 (14)	0.0366 (16)	0.0012 (12)	0.0128 (13)	−0.0005 (12)
C17	0.0407 (16)	0.0360 (16)	0.0260 (15)	0.0036 (13)	0.0124 (13)	0.0020 (12)
C18	0.0203 (12)	0.0262 (14)	0.0216 (13)	0.0019 (11)	0.0090 (10)	0.0012 (10)
C19	0.0167 (12)	0.0217 (13)	0.0255 (14)	0.0018 (10)	0.0092 (10)	−0.0001 (10)
C20	0.0366 (15)	0.0262 (15)	0.0338 (15)	0.0042 (12)	0.0138 (13)	−0.0022 (12)
N3	0.0218 (11)	0.0269 (12)	0.0248 (12)	−0.0018 (9)	0.0085 (9)	0.0040 (9)
N4	0.0210 (11)	0.0246 (12)	0.0280 (12)	−0.0008 (9)	0.0065 (9)	0.0045 (9)
C21	0.0411 (16)	0.0412 (17)	0.0256 (15)	−0.0041 (14)	0.0107 (13)	−0.0016 (12)
C22	0.0226 (13)	0.0259 (14)	0.0241 (13)	−0.0055 (11)	0.0102 (11)	−0.0013 (11)
C23	0.0193 (12)	0.0258 (14)	0.0280 (14)	−0.0045 (11)	0.0092 (11)	0.0008 (11)
C24	0.0367 (16)	0.0260 (15)	0.0431 (17)	−0.0004 (12)	0.0163 (13)	−0.0002 (12)
C25	0.0417 (17)	0.0433 (18)	0.0252 (15)	−0.0040 (14)	0.0039 (13)	0.0001 (13)
C26	0.0224 (13)	0.0272 (14)	0.0244 (14)	−0.0008 (11)	0.0080 (11)	0.0018 (11)
C27	0.0234 (13)	0.0216 (13)	0.0257 (14)	−0.0010 (11)	0.0099 (11)	0.0019 (10)
C28	0.0443 (17)	0.0309 (16)	0.0335 (16)	0.0047 (13)	0.0116 (13)	−0.0008 (12)

Geometric parameters (Å, º)

C29—C42	1.398 (3)	C2—C3	1.377 (3)
C29—C43	1.417 (3)	C3—C4	1.378 (3)
C29—C30	1.434 (4)	C3—H3A	0.9300
C30—C31	1.353 (3)	C4—C5	1.395 (3)
C30—H30	0.9300	C5—C6	1.377 (3)
C31—C32	1.423 (3)	C6—H6	0.9300
C31—H31	0.9300	N1—C19	1.339 (3)
C32—C33	1.392 (3)	N1—C14	1.342 (3)
C32—C44	1.420 (3)	N2—C15	1.338 (3)
C33—C34	1.384 (3)	N2—C18	1.343 (3)
C33—H33	0.9300	C13—C14	1.495 (3)
C34—C35	1.379 (3)	C13—H13A	0.9600
C34—H34	0.9300	C13—H13B	0.9600
C35—C36	1.387 (3)	C13—H13C	0.9600
C35—H35	0.9300	C14—C15	1.398 (3)
C36—C44	1.426 (3)	C15—C16	1.501 (3)
C36—C37	1.435 (3)	C16—H16A	0.9600
C37—C38	1.329 (3)	C16—H16B	0.9600
C37—H37	0.9300	C16—H16C	0.9600
C38—C39	1.438 (3)	C17—C18	1.502 (3)
C38—H38	0.9300	C17—H17A	0.9600
C39—C40	1.387 (3)	C17—H17B	0.9600
C39—C43	1.421 (3)	C17—H17C	0.9600
C40—C41	1.384 (4)	C18—C19	1.389 (3)
C40—H40	0.9300	C19—C20	1.496 (3)
C41—C42	1.370 (4)	C20—H20A	0.9600
C41—H41	0.9300	C20—H20B	0.9600
C42—H42	0.9300	C20—H20C	0.9600
C43—C44	1.424 (3)	N3—C27	1.339 (3)
Cl1—C8	1.734 (2)	N3—C22	1.345 (3)
Cl2—C10	1.728 (2)	N4—C23	1.337 (3)
O1—C7	1.347 (3)	N4—C26	1.344 (3)
O1—H1	0.8200	C21—C22	1.496 (3)
O2—C11	1.345 (3)	C21—H21A	0.9600
O2—H2	0.8200	C21—H21B	0.9600
C7—C12	1.386 (3)	C21—H21C	0.9600
C7—C8	1.400 (3)	C22—C23	1.394 (3)
C8—C9	1.381 (3)	C23—C24	1.500 (3)
C9—C10	1.378 (3)	C24—H24A	0.9600
C9—H9	0.9300	C24—H24B	0.9600
C10—C11	1.399 (3)	C24—H24C	0.9600
C11—C12	1.386 (3)	C25—C26	1.499 (3)
C12—H12	0.9300	C25—H25A	0.9600
Cl3—C4	1.733 (2)	C25—H25B	0.9600
Cl4—C2	1.736 (2)	C25—H25C	0.9600
O3—C5	1.347 (3)	C26—C27	1.396 (3)
O3—H3	0.8200	C27—C28	1.498 (3)
O4—C1	1.355 (3)	C28—H28A	0.9600
O4—H4	0.8200	C28—H28B	0.9600
C1—C6	1.387 (3)	C28—H28C	0.9600
C1—C2	1.395 (3)
C42—C29—C43	118.4 (2)	O3—C5—C6	123.0 (2)
C42—C29—C30	123.2 (2)	O3—C5—C4	118.5 (2)
C43—C29—C30	118.3 (2)	C6—C5—C4	118.5 (2)
C31—C30—C29	121.1 (2)	C5—C6—C1	121.9 (2)
C31—C30—H30	119.5	C5—C6—H6	119.0
C29—C30—H30	119.5	C1—C6—H6	119.0
C30—C31—C32	122.0 (2)	C19—N1—C14	119.5 (2)
C30—C31—H31	119.0	C15—N2—C18	119.17 (19)
C32—C31—H31	119.0	C14—C13—H13A	109.5
C33—C32—C44	118.8 (2)	C14—C13—H13B	109.5
C33—C32—C31	122.8 (2)	H13A—C13—H13B	109.5
C44—C32—C31	118.4 (2)	C14—C13—H13C	109.5
C34—C33—C32	120.6 (2)	H13A—C13—H13C	109.5
C34—C33—H33	119.7	H13B—C13—H13C	109.5
C32—C33—H33	119.7	N1—C14—C15	119.8 (2)
C35—C34—C33	121.1 (2)	N1—C14—C13	117.7 (2)
C35—C34—H34	119.5	C15—C14—C13	122.5 (2)
C33—C34—H34	119.5	N2—C15—C14	120.6 (2)
C34—C35—C36	120.6 (2)	N2—C15—C16	117.5 (2)
C34—C35—H35	119.7	C14—C15—C16	121.8 (2)
C36—C35—H35	119.7	C15—C16—H16A	109.5
C35—C36—C44	119.1 (2)	C15—C16—H16B	109.5
C35—C36—C37	123.0 (2)	H16A—C16—H16B	109.5
C44—C36—C37	117.9 (2)	C15—C16—H16C	109.5
C38—C37—C36	121.9 (2)	H16A—C16—H16C	109.5
C38—C37—H37	119.0	H16B—C16—H16C	109.5
C36—C37—H37	119.0	C18—C17—H17A	109.5
C37—C38—C39	121.8 (2)	C18—C17—H17B	109.5
C37—C38—H38	119.1	H17A—C17—H17B	109.5
C39—C38—H38	119.1	C18—C17—H17C	109.5
C40—C39—C43	118.9 (2)	H17A—C17—H17C	109.5
C40—C39—C38	122.7 (2)	H17B—C17—H17C	109.5
C43—C39—C38	118.4 (2)	N2—C18—C19	120.3 (2)
C41—C40—C39	120.7 (3)	N2—C18—C17	117.3 (2)
C41—C40—H40	119.6	C19—C18—C17	122.3 (2)
C39—C40—H40	119.6	N1—C19—C18	120.5 (2)
C42—C41—C40	120.8 (3)	N1—C19—C20	117.4 (2)
C42—C41—H41	119.6	C18—C19—C20	122.2 (2)
C40—C41—H41	119.6	C19—C20—H20A	109.5
C41—C42—C29	121.1 (3)	C19—C20—H20B	109.5
C41—C42—H42	119.4	H20A—C20—H20B	109.5
C29—C42—H42	119.4	C19—C20—H20C	109.5
C29—C43—C39	120.0 (2)	H20A—C20—H20C	109.5
C29—C43—C44	120.4 (2)	H20B—C20—H20C	109.5
C39—C43—C44	119.6 (2)	C27—N3—C22	118.9 (2)
C32—C44—C43	119.8 (2)	C23—N4—C26	119.2 (2)
C32—C44—C36	119.8 (2)	C22—C21—H21A	109.5
C43—C44—C36	120.4 (2)	C22—C21—H21B	109.5
C7—O1—H1	109.5	H21A—C21—H21B	109.5
C11—O2—H2	109.5	C22—C21—H21C	109.5
O1—C7—C12	123.2 (2)	H21A—C21—H21C	109.5
O1—C7—C8	118.8 (2)	H21B—C21—H21C	109.5
C12—C7—C8	118.0 (2)	N3—C22—C23	120.2 (2)
C9—C8—C7	120.7 (2)	N3—C22—C21	117.5 (2)
C9—C8—Cl1	119.97 (18)	C23—C22—C21	122.3 (2)
C7—C8—Cl1	119.27 (17)	N4—C23—C22	120.8 (2)
C10—C9—C8	120.1 (2)	N4—C23—C24	117.7 (2)
C10—C9—H9	119.9	C22—C23—C24	121.4 (2)
C8—C9—H9	119.9	C23—C24—H24A	109.5
C9—C10—C11	120.6 (2)	C23—C24—H24B	109.5
C9—C10—Cl2	120.14 (18)	H24A—C24—H24B	109.5
C11—C10—Cl2	119.30 (18)	C23—C24—H24C	109.5
O2—C11—C12	123.0 (2)	H24A—C24—H24C	109.5
O2—C11—C10	118.7 (2)	H24B—C24—H24C	109.5
C12—C11—C10	118.3 (2)	C26—C25—H25A	109.5
C7—C12—C11	122.2 (2)	C26—C25—H25B	109.5
C7—C12—H12	118.9	H25A—C25—H25B	109.5
C11—C12—H12	118.9	C26—C25—H25C	109.5
C5—O3—H3	109.5	H25A—C25—H25C	109.5
C1—O4—H4	109.5	H25B—C25—H25C	109.5
O4—C1—C6	122.9 (2)	N4—C26—C27	120.0 (2)
O4—C1—C2	118.9 (2)	N4—C26—C25	118.0 (2)
C6—C1—C2	118.2 (2)	C27—C26—C25	122.0 (2)
C3—C2—C1	120.8 (2)	N3—C27—C26	120.9 (2)
C3—C2—Cl4	119.49 (18)	N3—C27—C28	117.6 (2)
C1—C2—Cl4	119.69 (18)	C26—C27—C28	121.5 (2)
C2—C3—C4	119.8 (2)	C27—C28—H28A	109.5
C2—C3—H3A	120.1	C27—C28—H28B	109.5
C4—C3—H3A	120.1	H28A—C28—H28B	109.5
C3—C4—C5	120.7 (2)	C27—C28—H28C	109.5
C3—C4—Cl3	120.53 (18)	H28A—C28—H28C	109.5
C5—C4—Cl3	118.75 (18)	H28B—C28—H28C	109.5
C42—C29—C30—C31	−178.8 (2)	Cl2—C10—C11—C12	176.61 (17)
C43—C29—C30—C31	0.7 (4)	O1—C7—C12—C11	179.7 (2)
C29—C30—C31—C32	−0.3 (4)	C8—C7—C12—C11	0.9 (3)
C30—C31—C32—C33	−179.7 (2)	O2—C11—C12—C7	−177.3 (2)
C30—C31—C32—C44	−0.7 (4)	C10—C11—C12—C7	1.9 (3)
C44—C32—C33—C34	−0.4 (4)	O4—C1—C2—C3	−179.9 (2)
C31—C32—C33—C34	178.5 (2)	C6—C1—C2—C3	0.2 (3)
C32—C33—C34—C35	0.0 (4)	O4—C1—C2—Cl4	−0.1 (3)
C33—C34—C35—C36	0.4 (4)	C6—C1—C2—Cl4	179.99 (17)
C34—C35—C36—C44	−0.2 (3)	C1—C2—C3—C4	−0.4 (3)
C34—C35—C36—C37	179.0 (2)	Cl4—C2—C3—C4	179.82 (17)
C35—C36—C37—C38	−178.7 (2)	C2—C3—C4—C5	0.7 (4)
C44—C36—C37—C38	0.6 (3)	C2—C3—C4—Cl3	−178.40 (18)
C36—C37—C38—C39	−1.5 (4)	C3—C4—C5—O3	−179.9 (2)
C37—C38—C39—C40	−179.6 (2)	Cl3—C4—C5—O3	−0.7 (3)
C37—C38—C39—C43	1.2 (3)	C3—C4—C5—C6	−0.9 (4)
C43—C39—C40—C41	−0.7 (3)	Cl3—C4—C5—C6	178.26 (18)
C38—C39—C40—C41	−180.0 (2)	O3—C5—C6—C1	179.6 (2)
C39—C40—C41—C42	0.0 (4)	C4—C5—C6—C1	0.7 (4)
C40—C41—C42—C29	0.4 (4)	O4—C1—C6—C5	179.8 (2)
C43—C29—C42—C41	0.0 (4)	C2—C1—C6—C5	−0.3 (4)
C30—C29—C42—C41	179.4 (2)	C19—N1—C14—C15	−1.6 (3)
C42—C29—C43—C39	−0.7 (3)	C19—N1—C14—C13	178.31 (19)
C30—C29—C43—C39	179.8 (2)	C18—N2—C15—C14	0.2 (3)
C42—C29—C43—C44	179.5 (2)	C18—N2—C15—C16	−179.2 (2)
C30—C29—C43—C44	0.0 (3)	N1—C14—C15—N2	1.1 (3)
C40—C39—C43—C29	1.1 (3)	C13—C14—C15—N2	−178.8 (2)
C38—C39—C43—C29	−179.7 (2)	N1—C14—C15—C16	−179.6 (2)
C40—C39—C43—C44	−179.1 (2)	C13—C14—C15—C16	0.5 (3)
C38—C39—C43—C44	0.1 (3)	C15—N2—C18—C19	−1.0 (3)
C33—C32—C44—C43	−179.6 (2)	C15—N2—C18—C17	177.8 (2)
C31—C32—C44—C43	1.4 (3)	C14—N1—C19—C18	0.8 (3)
C33—C32—C44—C36	0.5 (3)	C14—N1—C19—C20	−178.8 (2)
C31—C32—C44—C36	−178.4 (2)	N2—C18—C19—N1	0.5 (3)
C29—C43—C44—C32	−1.0 (3)	C17—C18—C19—N1	−178.3 (2)
C39—C43—C44—C32	179.2 (2)	N2—C18—C19—C20	−179.9 (2)
C29—C43—C44—C36	178.8 (2)	C17—C18—C19—C20	1.4 (3)
C39—C43—C44—C36	−1.0 (3)	C27—N3—C22—C23	−0.6 (3)
C35—C36—C44—C32	−0.2 (3)	C27—N3—C22—C21	−179.9 (2)
C37—C36—C44—C32	−179.5 (2)	C26—N4—C23—C22	−0.9 (3)
C35—C36—C44—C43	180.0 (2)	C26—N4—C23—C24	178.7 (2)
C37—C36—C44—C43	0.7 (3)	N3—C22—C23—N4	1.4 (3)
O1—C7—C8—C9	178.4 (2)	C21—C22—C23—N4	−179.3 (2)
C12—C7—C8—C9	−2.7 (3)	N3—C22—C23—C24	−178.1 (2)
O1—C7—C8—Cl1	−0.4 (3)	C21—C22—C23—C24	1.2 (3)
C12—C7—C8—Cl1	178.57 (17)	C23—N4—C26—C27	−0.4 (3)
C7—C8—C9—C10	1.7 (3)	C23—N4—C26—C25	−178.9 (2)
Cl1—C8—C9—C10	−179.52 (17)	C22—N3—C27—C26	−0.7 (3)
C8—C9—C10—C11	1.1 (3)	C22—N3—C27—C28	179.2 (2)
C8—C9—C10—Cl2	−178.36 (17)	N4—C26—C27—N3	1.2 (3)
C9—C10—C11—O2	176.4 (2)	C25—C26—C27—N3	179.7 (2)
Cl2—C10—C11—O2	−4.2 (3)	N4—C26—C27—C28	−178.7 (2)
C9—C10—C11—C12	−2.8 (3)	C25—C26—C27—C28	−0.2 (4)

(30CRES-PHE-PYR)

Crystal data

C84H54Cl4N4O4	F(000) = 2744
Mr = 1325.11	Dx = 1.367 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
a = 33.873 (7) Å	Cell parameters from 15951 reflections
b = 10.374 (2) Å	θ = 3.0–28.3°
c = 18.332 (4) Å	µ = 0.24 mm^−1
β = 91.186 (6)°	T = 150 K
V = 6441 (2) Å^3	Prism, red
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2992 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.136
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −43→43
Tmin = 0.651, Tmax = 1.000	k = −13→13
32417 measured reflections	l = −23→23
7363 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.078	H-atom parameters constrained
wR(F^2) = 0.205	w = 1/[σ^2(Fo^2) + (0.068P)^2 + 1.3656P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
7363 reflections	Δρmax = 0.26 e Å^−3
435 parameters	Δρmin = −0.34 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.39237 (3)	−0.02075 (13)	0.77470 (7)	0.0796 (4)
Cl2	0.43057 (3)	0.47769 (13)	0.72874 (7)	0.0818 (4)
O2	0.32313 (8)	0.0394 (3)	0.68232 (15)	0.0575 (8)
H2	0.304329	0.060846	0.656152	0.086*
O1	0.35872 (8)	0.4805 (3)	0.63652 (15)	0.0606 (8)
H1	0.340178	0.474161	0.607270	0.091*
N2	0.23957 (9)	0.4064 (3)	0.42075 (15)	0.0415 (8)
N1	0.29864 (9)	0.4416 (3)	0.53032 (16)	0.0423 (8)
C1	0.34774 (11)	0.1408 (4)	0.69182 (19)	0.0430 (9)
C13	0.27801 (11)	0.4102 (3)	0.40435 (19)	0.0399 (9)
C5	0.36541 (11)	0.3647 (4)	0.6689 (2)	0.0462 (10)
C35	0.24525 (11)	0.7561 (3)	0.53758 (17)	0.0369 (8)
C7	0.26012 (11)	0.4357 (3)	0.54723 (19)	0.0399 (9)
C36	0.27587 (11)	0.7687 (3)	0.59090 (19)	0.0418 (9)
C12	0.23020 (10)	0.4177 (3)	0.4916 (2)	0.0398 (9)
C18	0.30786 (11)	0.4278 (3)	0.4593 (2)	0.0439 (9)
C6	0.34050 (10)	0.2599 (4)	0.65868 (18)	0.0424 (9)
H6	0.318190	0.269216	0.628719	0.051*
C8	0.24820 (12)	0.4483 (3)	0.62101 (19)	0.0472 (10)
H8	0.267182	0.460218	0.657768	0.057*
C40	0.20562 (11)	0.7568 (3)	0.55845 (19)	0.0436 (9)
C11	0.19009 (11)	0.4125 (4)	0.5123 (2)	0.0490 (10)
H11	0.170336	0.401096	0.476923	0.059*
C2	0.38121 (11)	0.1279 (4)	0.73623 (19)	0.0498 (11)
C9	0.20972 (13)	0.4431 (4)	0.6381 (2)	0.0546 (11)
H9	0.202452	0.452098	0.686480	0.066*
C37	0.26599 (14)	0.7825 (4)	0.6635 (2)	0.0534 (11)
H37	0.285887	0.792659	0.698774	0.064*
C14	0.28971 (12)	0.3974 (4)	0.3310 (2)	0.0517 (11)
H14	0.270686	0.387313	0.294125	0.062*
C41	0.17529 (12)	0.7442 (4)	0.5037 (2)	0.0535 (11)
H41	0.148997	0.744284	0.517347	0.064*
C4	0.39868 (10)	0.3490 (5)	0.7146 (2)	0.0527 (11)
C42	0.18394 (12)	0.7324 (4)	0.4331 (2)	0.0523 (11)
H42	0.163494	0.724801	0.398678	0.063*
C3	0.40611 (11)	0.2316 (5)	0.7473 (2)	0.0564 (12)
H3	0.428329	0.222149	0.777512	0.068*
C38	0.22718 (15)	0.7813 (4)	0.6842 (2)	0.0602 (12)
H38	0.221352	0.788557	0.733379	0.072*
C39	0.19692 (13)	0.7695 (4)	0.6338 (2)	0.0543 (11)
H39	0.170851	0.769922	0.648715	0.065*
C10	0.18038 (13)	0.4241 (4)	0.5836 (2)	0.0574 (11)
H10	0.154017	0.419375	0.596506	0.069*
C15	0.32835 (14)	0.3997 (4)	0.3143 (2)	0.0628 (12)
H15	0.335631	0.389713	0.265945	0.075*
C17	0.34773 (12)	0.4301 (4)	0.4397 (2)	0.0606 (12)
H17	0.367349	0.440669	0.475468	0.073*
C16	0.35771 (13)	0.4168 (4)	0.3685 (3)	0.0688 (13)
H16	0.384142	0.419128	0.355821	0.083*
C33	0.45405 (11)	0.8518 (5)	0.4665 (3)	0.0607 (12)
C34	0.45977 (11)	0.9794 (5)	0.4404 (2)	0.0630 (13)
C26	0.44068 (14)	1.0853 (6)	0.4745 (3)	0.0745 (14)
C22	0.48449 (14)	0.9996 (7)	0.3804 (3)	0.0807 (16)
C27	0.41760 (14)	1.0609 (7)	0.5355 (3)	0.0857 (17)
H27	0.405238	1.129847	0.558037	0.103*
C29	0.43037 (13)	0.8328 (6)	0.5294 (3)	0.0704 (14)
C19	0.47245 (15)	0.7471 (7)	0.4325 (3)	0.0814 (16)
C28	0.41266 (14)	0.9435 (7)	0.5624 (3)	0.0872 (17)
H28	0.397401	0.932595	0.603563	0.105*
C21	0.50326 (17)	0.8920 (10)	0.3485 (3)	0.108 (3)
H21	0.520197	0.905375	0.309987	0.130*
C25	0.44672 (18)	1.2105 (6)	0.4460 (4)	0.101 (2)
H25	0.434344	1.281426	0.466570	0.121*
C23	0.49019 (19)	1.1257 (10)	0.3554 (3)	0.111 (2)
H23	0.506939	1.141068	0.316744	0.134*
C20	0.49739 (19)	0.7734 (9)	0.3720 (4)	0.110 (3)
H20	0.509738	0.705148	0.348744	0.132*
C32	0.46591 (19)	0.6220 (7)	0.4598 (5)	0.110 (2)
H32	0.476841	0.550659	0.437048	0.132*
C24	0.4711 (2)	1.2260 (8)	0.3876 (5)	0.121 (3)
H24	0.474857	1.308570	0.369253	0.145*
C30	0.42580 (17)	0.7089 (8)	0.5550 (4)	0.106 (2)
H30	0.410780	0.694581	0.596092	0.128*
C31	0.4431 (2)	0.6064 (8)	0.5208 (5)	0.126 (3)
H31	0.439289	0.523935	0.539242	0.152*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0641 (7)	0.1032 (11)	0.0712 (8)	0.0189 (7)	−0.0053 (6)	0.0342 (7)
Cl2	0.0580 (7)	0.1021 (11)	0.0848 (9)	−0.0214 (7)	−0.0105 (6)	−0.0174 (7)
O2	0.0598 (18)	0.0582 (19)	0.0540 (18)	−0.0020 (15)	−0.0142 (15)	0.0097 (14)
O1	0.0629 (19)	0.055 (2)	0.063 (2)	−0.0076 (15)	−0.0156 (15)	0.0003 (15)
N2	0.052 (2)	0.0382 (19)	0.0344 (18)	−0.0010 (15)	−0.0044 (15)	−0.0011 (14)
N1	0.050 (2)	0.0357 (19)	0.0408 (19)	0.0004 (15)	−0.0052 (16)	0.0033 (14)
C1	0.044 (2)	0.055 (3)	0.030 (2)	0.002 (2)	0.0015 (18)	−0.0014 (19)
C13	0.047 (2)	0.034 (2)	0.038 (2)	−0.0027 (18)	0.0022 (19)	0.0016 (17)
C5	0.046 (2)	0.055 (3)	0.038 (2)	0.000 (2)	−0.0005 (19)	−0.007 (2)
C35	0.048 (2)	0.024 (2)	0.0383 (19)	−0.0026 (16)	−0.0002 (19)	0.0055 (17)
C7	0.052 (2)	0.030 (2)	0.038 (2)	0.0020 (18)	−0.0008 (19)	0.0047 (16)
C36	0.060 (3)	0.026 (2)	0.039 (2)	−0.0060 (18)	−0.001 (2)	0.0041 (17)
C12	0.048 (2)	0.031 (2)	0.041 (2)	−0.0006 (18)	0.0048 (19)	0.0023 (17)
C18	0.047 (2)	0.037 (2)	0.048 (2)	−0.0003 (18)	−0.003 (2)	0.0048 (19)
C6	0.040 (2)	0.055 (3)	0.032 (2)	0.0021 (19)	−0.0062 (17)	−0.0038 (19)
C8	0.068 (3)	0.039 (2)	0.034 (2)	0.005 (2)	−0.004 (2)	0.0032 (18)
C40	0.052 (2)	0.034 (2)	0.045 (2)	0.0004 (18)	0.005 (2)	0.0018 (18)
C11	0.049 (2)	0.046 (3)	0.052 (3)	0.0000 (19)	−0.003 (2)	−0.002 (2)
C2	0.039 (2)	0.077 (3)	0.033 (2)	0.013 (2)	0.0029 (18)	0.009 (2)
C9	0.079 (3)	0.042 (3)	0.043 (2)	0.013 (2)	0.014 (2)	−0.0004 (19)
C37	0.077 (3)	0.041 (3)	0.042 (2)	−0.005 (2)	−0.005 (2)	0.0001 (19)
C14	0.064 (3)	0.050 (3)	0.042 (2)	0.000 (2)	0.005 (2)	−0.0033 (19)
C41	0.048 (2)	0.046 (3)	0.066 (3)	−0.004 (2)	0.002 (2)	0.003 (2)
C4	0.034 (2)	0.082 (4)	0.042 (2)	−0.004 (2)	−0.0053 (19)	−0.019 (2)
C42	0.053 (3)	0.045 (3)	0.057 (3)	−0.006 (2)	−0.019 (2)	0.006 (2)
C3	0.036 (2)	0.087 (4)	0.046 (2)	0.007 (2)	−0.0074 (19)	0.002 (2)
C38	0.094 (3)	0.049 (3)	0.038 (2)	−0.005 (2)	0.005 (3)	0.000 (2)
C39	0.063 (3)	0.044 (3)	0.056 (3)	0.000 (2)	0.024 (2)	0.003 (2)
C10	0.062 (3)	0.056 (3)	0.055 (3)	0.002 (2)	0.011 (2)	0.001 (2)
C15	0.078 (3)	0.060 (3)	0.051 (3)	0.003 (3)	0.020 (3)	0.002 (2)
C17	0.047 (3)	0.073 (3)	0.062 (3)	0.001 (2)	−0.003 (2)	0.000 (2)
C16	0.057 (3)	0.084 (4)	0.065 (3)	0.001 (3)	0.012 (3)	0.004 (3)
C33	0.035 (2)	0.081 (4)	0.066 (3)	−0.003 (2)	−0.014 (2)	−0.007 (3)
C34	0.035 (2)	0.093 (4)	0.061 (3)	0.005 (3)	−0.018 (2)	−0.011 (3)
C26	0.046 (3)	0.089 (4)	0.087 (4)	0.003 (3)	−0.028 (3)	−0.011 (3)
C22	0.049 (3)	0.132 (5)	0.060 (3)	−0.013 (3)	−0.020 (3)	0.009 (4)
C27	0.044 (3)	0.117 (5)	0.096 (5)	0.004 (3)	−0.005 (3)	−0.039 (4)
C29	0.045 (3)	0.085 (4)	0.081 (4)	−0.011 (3)	−0.015 (3)	0.001 (3)
C19	0.053 (3)	0.093 (5)	0.097 (4)	0.015 (3)	−0.018 (3)	−0.044 (4)
C28	0.046 (3)	0.136 (6)	0.079 (4)	−0.009 (4)	0.005 (3)	−0.024 (4)
C21	0.052 (3)	0.211 (9)	0.062 (4)	0.006 (5)	−0.005 (3)	−0.038 (5)
C25	0.077 (4)	0.087 (5)	0.136 (6)	0.002 (4)	−0.049 (4)	−0.005 (4)
C23	0.080 (4)	0.180 (8)	0.073 (4)	−0.033 (5)	−0.022 (3)	0.025 (5)
C20	0.070 (4)	0.165 (7)	0.094 (5)	0.033 (5)	−0.023 (4)	−0.073 (5)
C32	0.079 (4)	0.087 (6)	0.163 (7)	0.017 (4)	−0.042 (5)	−0.038 (5)
C24	0.106 (6)	0.135 (7)	0.120 (6)	−0.024 (5)	−0.046 (5)	0.036 (6)
C30	0.070 (4)	0.123 (6)	0.125 (5)	−0.020 (4)	−0.026 (4)	0.022 (5)
C31	0.088 (5)	0.098 (6)	0.191 (9)	−0.019 (5)	−0.060 (5)	0.012 (6)

Geometric parameters (Å, º)

Cl1—C2	1.734 (4)	C4—C3	1.379 (6)
Cl2—C4	1.733 (4)	C42—H42	0.9300
O2—C1	1.352 (4)	C3—H3	0.9300
O2—H2	0.8200	C38—C39	1.371 (5)
O1—C5	1.357 (4)	C38—H38	0.9300
O1—H1	0.8200	C39—H39	0.9300
N2—C13	1.343 (4)	C10—H10	0.9300
N2—C12	1.348 (4)	C15—C16	1.404 (6)
N1—C7	1.349 (4)	C15—H15	0.9300
N1—C18	1.353 (4)	C17—C16	1.362 (5)
C1—C2	1.389 (5)	C17—H17	0.9300
C1—C6	1.396 (5)	C16—H16	0.9300
C13—C14	1.416 (5)	C33—C19	1.404 (6)
C13—C18	1.424 (5)	C33—C34	1.423 (6)
C5—C6	1.386 (5)	C33—C29	1.432 (6)
C5—C4	1.400 (5)	C34—C22	1.412 (6)
C35—C40	1.404 (5)	C34—C26	1.425 (6)
C35—C36	1.416 (5)	C26—C27	1.401 (7)
C35—C35^i	1.427 (6)	C26—C25	1.417 (7)
C7—C8	1.426 (5)	C22—C23	1.401 (8)
C7—C12	1.435 (5)	C22—C21	1.416 (8)
C36—C37	1.387 (5)	C27—C28	1.326 (7)
C36—C42^i	1.439 (5)	C27—H27	0.9300
C12—C11	1.419 (5)	C29—C30	1.378 (7)
C18—C17	1.405 (5)	C29—C28	1.435 (7)
C6—H6	0.9300	C19—C32	1.411 (8)
C8—C9	1.348 (5)	C19—C20	1.433 (8)
C8—H8	0.9300	C28—H28	0.9300
C40—C39	1.424 (5)	C21—C20	1.321 (8)
C40—C41	1.427 (5)	C21—H21	0.9300
C11—C10	1.359 (5)	C25—C24	1.376 (8)
C11—H11	0.9300	C25—H25	0.9300
C2—C3	1.380 (5)	C23—C24	1.365 (9)
C9—C10	1.409 (5)	C23—H23	0.9300
C9—H9	0.9300	C20—H20	0.9300
C37—C38	1.375 (5)	C32—C31	1.382 (9)
C37—H37	0.9300	C32—H32	0.9300
C14—C15	1.351 (5)	C24—H24	0.9300
C14—H14	0.9300	C30—C31	1.371 (9)
C41—C42	1.339 (5)	C30—H30	0.9300
C41—H41	0.9300	C31—H31	0.9300
C1—O2—H2	109.5	C39—C38—H38	119.3
C5—O1—H1	109.5	C37—C38—H38	119.3
C13—N2—C12	117.5 (3)	C38—C39—C40	119.7 (4)
C7—N1—C18	117.4 (3)	C38—C39—H39	120.2
O2—C1—C2	119.6 (4)	C40—C39—H39	120.2
O2—C1—C6	122.0 (3)	C11—C10—C9	120.9 (4)
C2—C1—C6	118.4 (4)	C11—C10—H10	119.6
N2—C13—C14	120.1 (3)	C9—C10—H10	119.6
N2—C13—C18	121.5 (3)	C14—C15—C16	121.1 (4)
C14—C13—C18	118.4 (4)	C14—C15—H15	119.4
O1—C5—C6	122.7 (3)	C16—C15—H15	119.4
O1—C5—C4	119.3 (4)	C16—C17—C18	120.2 (4)
C6—C5—C4	118.0 (4)	C16—C17—H17	119.9
C40—C35—C36	120.1 (3)	C18—C17—H17	119.9
C40—C35—C35^i	120.0 (4)	C17—C16—C15	120.4 (4)
C36—C35—C35^i	119.9 (4)	C17—C16—H16	119.8
N1—C7—C8	120.5 (3)	C15—C16—H16	119.8
N1—C7—C12	121.0 (3)	C19—C33—C34	120.4 (5)
C8—C7—C12	118.5 (4)	C19—C33—C29	120.8 (5)
C37—C36—C35	119.0 (4)	C34—C33—C29	118.8 (5)
C37—C36—C42^i	122.8 (4)	C22—C34—C33	119.2 (5)
C35—C36—C42^i	118.2 (3)	C22—C34—C26	120.6 (6)
N2—C12—C11	120.0 (3)	C33—C34—C26	120.2 (5)
N2—C12—C7	121.3 (3)	C27—C26—C25	123.1 (6)
C11—C12—C7	118.7 (3)	C27—C26—C34	118.5 (5)
N1—C18—C17	119.1 (4)	C25—C26—C34	118.3 (6)
N1—C18—C13	121.3 (3)	C23—C22—C34	118.8 (6)
C17—C18—C13	119.6 (4)	C23—C22—C21	122.3 (7)
C5—C6—C1	122.3 (3)	C34—C22—C21	118.9 (6)
C5—C6—H6	118.9	C28—C27—C26	122.7 (6)
C1—C6—H6	118.9	C28—C27—H27	118.7
C9—C8—C7	120.7 (4)	C26—C27—H27	118.7
C9—C8—H8	119.6	C30—C29—C33	118.1 (6)
C7—C8—H8	119.6	C30—C29—C28	123.5 (6)
C35—C40—C39	118.9 (4)	C33—C29—C28	118.4 (5)
C35—C40—C41	119.1 (3)	C33—C19—C32	118.6 (6)
C39—C40—C41	122.0 (4)	C33—C19—C20	118.1 (6)
C10—C11—C12	120.4 (4)	C32—C19—C20	123.3 (7)
C10—C11—H11	119.8	C27—C28—C29	121.4 (5)
C12—C11—H11	119.8	C27—C28—H28	119.3
C3—C2—C1	120.0 (4)	C29—C28—H28	119.3
C3—C2—Cl1	120.4 (3)	C20—C21—C22	121.9 (7)
C1—C2—Cl1	119.5 (3)	C20—C21—H21	119.0
C8—C9—C10	120.8 (4)	C22—C21—H21	119.0
C8—C9—H9	119.6	C24—C25—C26	119.1 (7)
C10—C9—H9	119.6	C24—C25—H25	120.4
C38—C37—C36	121.0 (4)	C26—C25—H25	120.4
C38—C37—H37	119.5	C24—C23—C22	120.0 (7)
C36—C37—H37	119.5	C24—C23—H23	120.0
C15—C14—C13	120.4 (4)	C22—C23—H23	120.0
C15—C14—H14	119.8	C21—C20—C19	121.6 (7)
C13—C14—H14	119.8	C21—C20—H20	119.2
C42—C41—C40	121.3 (4)	C19—C20—H20	119.2
C42—C41—H41	119.3	C31—C32—C19	119.3 (7)
C40—C41—H41	119.3	C31—C32—H32	120.4
C3—C4—C5	120.0 (4)	C19—C32—H32	120.4
C3—C4—Cl2	120.5 (3)	C23—C24—C25	123.1 (8)
C5—C4—Cl2	119.5 (4)	C23—C24—H24	118.5
C41—C42—C36^i	121.5 (4)	C25—C24—H24	118.5
C41—C42—H42	119.2	C31—C30—C29	121.0 (7)
C36^i—C42—H42	119.2	C31—C30—H30	119.5
C4—C3—C2	121.3 (4)	C29—C30—H30	119.5
C4—C3—H3	119.4	C30—C31—C32	122.0 (8)
C2—C3—H3	119.4	C30—C31—H31	119.0
C39—C38—C37	121.4 (4)	C32—C31—H31	119.0

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

(31CRES-DMP-PYR)

Crystal data

C28H22Cl2N2O2	Z = 2
Mr = 489.37	F(000) = 508
Triclinic, P1	Dx = 1.405 Mg m^−3
a = 8.8453 (13) Å	Mo Kα radiation, λ = 0.71075 Å
b = 10.4891 (15) Å	Cell parameters from 10718 reflections
c = 12.6940 (19) Å	θ = 3.2–27.6°
α = 94.129 (7)°	µ = 0.31 mm^−1
β = 94.866 (7)°	T = 150 K
γ = 98.239 (7)°	Prism, colorless
V = 1157.1 (3) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	4119 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.032
profile data from ω–scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −11→11
Tmin = 0.800, Tmax = 1.000	k = −13→13
12258 measured reflections	l = −16→16
5291 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.0838P)^2 + 0.247P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
5291 reflections	Δρmax = 0.38 e Å^−3
311 parameters	Δρmin = −0.36 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl01	1.02959 (6)	0.68667 (6)	0.08882 (4)	0.03253 (16)
Cl02	1.11357 (6)	0.23705 (5)	0.24945 (4)	0.03074 (16)
O2	0.93694 (17)	0.32455 (14)	0.41690 (12)	0.0285 (3)
H2	0.859281	0.332969	0.446050	0.043*
O1	0.84868 (17)	0.72004 (15)	0.26951 (13)	0.0291 (4)
H1	0.787264	0.719435	0.314426	0.044*
N1	0.66632 (19)	0.34726 (16)	0.50690 (13)	0.0218 (4)
N2	0.39818 (19)	0.30727 (16)	0.60654 (13)	0.0214 (4)
C24	0.5297 (2)	0.32823 (18)	0.44994 (16)	0.0211 (4)
C27	0.5353 (2)	0.32621 (18)	0.66345 (16)	0.0207 (4)
C26	0.6687 (2)	0.34588 (19)	0.61191 (16)	0.0212 (4)
H26	0.763077	0.358546	0.652424	0.025*
C2	0.9548 (2)	0.41021 (19)	0.34255 (16)	0.0220 (4)
C22	0.4328 (2)	−0.01332 (18)	0.46247 (16)	0.0216 (4)
C4	1.0627 (2)	0.4679 (2)	0.18094 (16)	0.0252 (5)
H4	1.121591	0.450104	0.125941	0.030*
C6	0.9108 (2)	0.6100 (2)	0.26842 (16)	0.0224 (4)
C14	0.5053 (2)	0.0681 (2)	0.01210 (15)	0.0236 (4)
C3	1.0399 (2)	0.3818 (2)	0.25794 (17)	0.0233 (4)
C5	0.9981 (2)	0.5796 (2)	0.18580 (16)	0.0239 (4)
C25	0.3962 (2)	0.30791 (19)	0.50115 (16)	0.0232 (4)
H25	0.301945	0.294239	0.460407	0.028*
C1	0.8940 (2)	0.5248 (2)	0.34687 (16)	0.0236 (4)
H1A	0.840331	0.545386	0.404086	0.028*
C23	0.5253 (3)	0.3302 (2)	0.33194 (16)	0.0272 (5)
H23A	0.552130	0.417458	0.314233	0.041*
H23B	0.423828	0.296163	0.300171	0.041*
H23C	0.597139	0.278119	0.305729	0.041*
C13	0.3727 (3)	0.1291 (2)	0.00019 (17)	0.0289 (5)
C17	0.4491 (3)	−0.01394 (19)	0.35222 (17)	0.0263 (5)
C15	0.7259 (3)	0.0354 (2)	0.38824 (18)	0.0295 (5)
H15	0.822237	0.050610	0.363411	0.035*
C28	0.5403 (3)	0.3277 (2)	0.78120 (17)	0.0292 (5)
H28A	0.507648	0.405628	0.809350	0.044*
H28B	0.643272	0.324378	0.810329	0.044*
H28C	0.473176	0.254202	0.799760	0.044*
C20	0.1564 (3)	−0.0670 (2)	0.42490 (19)	0.0309 (5)
H20	0.059246	−0.086203	0.447883	0.037*
C9	0.6502 (2)	0.1428 (2)	0.04835 (16)	0.0280 (5)
C16	0.6004 (3)	0.0107 (2)	0.31812 (18)	0.0287 (5)
H16	0.611820	0.009630	0.245921	0.034*
C21	0.2854 (2)	−0.03872 (18)	0.49956 (17)	0.0246 (4)
C7	0.7712 (3)	−0.0503 (3)	0.03708 (19)	0.0359 (6)
H7	0.859079	−0.089127	0.045646	0.043*
C10	0.6580 (3)	0.2758 (2)	0.07180 (18)	0.0361 (6)
H10	0.751888	0.325325	0.096226	0.043*
C19	0.1722 (3)	−0.0667 (2)	0.3173 (2)	0.0328 (5)
H19	0.085368	−0.084739	0.268892	0.039*
C18	0.3157 (3)	−0.0398 (2)	0.28101 (18)	0.0295 (5)
H18	0.323884	−0.038831	0.208505	0.035*
C8	0.7821 (3)	0.0782 (3)	0.05991 (18)	0.0346 (5)
H8	0.877172	0.126070	0.083677	0.041*
C12	0.3877 (3)	0.2629 (2)	0.02408 (18)	0.0375 (6)
H12	0.301626	0.304159	0.016175	0.045*
C11	0.5291 (3)	0.3348 (2)	0.05935 (18)	0.0405 (6)
H11	0.536959	0.423676	0.074749	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl01	0.0332 (3)	0.0432 (3)	0.0235 (3)	0.0063 (2)	0.0084 (2)	0.0106 (2)
Cl02	0.0259 (3)	0.0307 (3)	0.0355 (3)	0.0086 (2)	0.0014 (2)	−0.0049 (2)
O2	0.0252 (8)	0.0307 (8)	0.0325 (9)	0.0057 (6)	0.0108 (6)	0.0093 (7)
O1	0.0262 (8)	0.0312 (8)	0.0335 (9)	0.0084 (6)	0.0122 (6)	0.0086 (7)
N1	0.0228 (9)	0.0219 (8)	0.0209 (9)	0.0023 (7)	0.0036 (7)	0.0027 (7)
N2	0.0203 (9)	0.0227 (9)	0.0230 (9)	0.0062 (7)	0.0074 (7)	0.0019 (7)
C24	0.0249 (10)	0.0177 (9)	0.0206 (10)	0.0029 (8)	0.0030 (8)	0.0019 (8)
C27	0.0252 (10)	0.0156 (9)	0.0219 (10)	0.0041 (7)	0.0046 (8)	0.0017 (8)
C26	0.0204 (10)	0.0214 (10)	0.0213 (10)	0.0025 (8)	0.0009 (8)	0.0013 (8)
C2	0.0157 (9)	0.0247 (10)	0.0243 (10)	−0.0013 (7)	0.0019 (8)	0.0013 (8)
C22	0.0252 (11)	0.0139 (9)	0.0271 (11)	0.0048 (7)	0.0080 (8)	0.0022 (8)
C4	0.0180 (10)	0.0371 (12)	0.0186 (10)	0.0013 (8)	0.0023 (8)	−0.0057 (9)
C6	0.0146 (9)	0.0279 (11)	0.0240 (10)	0.0006 (8)	0.0022 (8)	0.0016 (8)
C14	0.0227 (10)	0.0346 (11)	0.0148 (10)	0.0038 (8)	0.0059 (8)	0.0071 (8)
C3	0.0175 (10)	0.0250 (10)	0.0254 (11)	0.0022 (8)	−0.0007 (8)	−0.0054 (8)
C5	0.0194 (10)	0.0313 (11)	0.0190 (10)	−0.0032 (8)	0.0006 (8)	0.0039 (8)
C25	0.0218 (10)	0.0239 (10)	0.0235 (10)	0.0033 (8)	0.0000 (8)	0.0018 (8)
C1	0.0178 (10)	0.0298 (11)	0.0239 (11)	0.0028 (8)	0.0073 (8)	0.0015 (8)
C23	0.0296 (12)	0.0304 (11)	0.0210 (11)	0.0008 (9)	0.0035 (8)	0.0038 (9)
C13	0.0305 (12)	0.0388 (13)	0.0212 (11)	0.0109 (9)	0.0085 (9)	0.0106 (9)
C17	0.0355 (12)	0.0185 (10)	0.0266 (11)	0.0066 (8)	0.0074 (9)	0.0027 (8)
C15	0.0315 (12)	0.0226 (11)	0.0373 (13)	0.0042 (9)	0.0177 (10)	0.0049 (9)
C28	0.0361 (13)	0.0306 (12)	0.0210 (11)	0.0041 (9)	0.0053 (9)	0.0023 (9)
C20	0.0262 (12)	0.0248 (11)	0.0429 (14)	0.0069 (9)	0.0066 (10)	0.0016 (10)
C9	0.0272 (11)	0.0400 (13)	0.0173 (10)	0.0010 (9)	0.0069 (8)	0.0071 (9)
C16	0.0378 (13)	0.0248 (11)	0.0267 (11)	0.0071 (9)	0.0164 (9)	0.0044 (9)
C21	0.0278 (11)	0.0140 (9)	0.0334 (12)	0.0040 (8)	0.0091 (9)	0.0022 (8)
C7	0.0228 (11)	0.0568 (16)	0.0331 (13)	0.0142 (10)	0.0071 (9)	0.0154 (11)
C10	0.0465 (15)	0.0378 (13)	0.0202 (11)	−0.0081 (11)	0.0058 (10)	0.0024 (10)
C19	0.0335 (13)	0.0246 (11)	0.0402 (14)	0.0081 (9)	−0.0028 (10)	0.0014 (10)
C18	0.0407 (13)	0.0221 (11)	0.0263 (11)	0.0070 (9)	0.0009 (9)	0.0037 (9)
C8	0.0218 (11)	0.0516 (15)	0.0290 (12)	−0.0027 (10)	0.0015 (9)	0.0120 (11)
C12	0.0510 (16)	0.0419 (14)	0.0264 (12)	0.0197 (12)	0.0154 (11)	0.0098 (10)
C11	0.0672 (19)	0.0327 (13)	0.0224 (12)	0.0053 (12)	0.0133 (11)	0.0016 (10)

Geometric parameters (Å, º)

Cl01—C5	1.738 (2)	C23—H23A	0.9600
Cl02—C3	1.736 (2)	C23—H23B	0.9600
O2—C2	1.353 (2)	C23—H23C	0.9600
O2—H2	0.8200	C13—C12	1.400 (3)
O1—C6	1.347 (2)	C13—C7^ii	1.438 (3)
O1—H1	0.8200	C17—C18	1.405 (3)
N1—C26	1.333 (3)	C17—C16	1.435 (3)
N1—C24	1.336 (3)	C15—C16	1.345 (3)
N2—C25	1.337 (3)	C15—C21^i	1.434 (3)
N2—C27	1.339 (3)	C15—H15	0.9300
C24—C25	1.393 (3)	C28—H28A	0.9600
C24—C23	1.497 (3)	C28—H28B	0.9600
C27—C26	1.394 (3)	C28—H28C	0.9600
C27—C28	1.490 (3)	C20—C19	1.384 (3)
C26—H26	0.9300	C20—C21	1.403 (3)
C2—C1	1.385 (3)	C20—H20	0.9300
C2—C3	1.402 (3)	C9—C10	1.396 (3)
C22—C17	1.419 (3)	C9—C8	1.433 (3)
C22—C21	1.419 (3)	C16—H16	0.9300
C22—C22^i	1.440 (4)	C7—C8	1.346 (4)
C4—C5	1.375 (3)	C7—H7	0.9300
C4—C3	1.385 (3)	C10—C11	1.376 (4)
C4—H4	0.9300	C10—H10	0.9300
C6—C1	1.388 (3)	C19—C18	1.386 (3)
C6—C5	1.399 (3)	C19—H19	0.9300
C14—C13	1.416 (3)	C18—H18	0.9300
C14—C9	1.424 (3)	C8—H8	0.9300
C14—C14^ii	1.428 (4)	C12—C11	1.385 (4)
C25—H25	0.9300	C12—H12	0.9300
C1—H1A	0.9300	C11—H11	0.9300
C2—O2—H2	109.5	C12—C13—C7^ii	123.0 (2)
C6—O1—H1	109.5	C14—C13—C7^ii	118.2 (2)
C26—N1—C24	117.85 (17)	C18—C17—C22	118.3 (2)
C25—N2—C27	117.60 (17)	C18—C17—C16	122.9 (2)
N1—C24—C25	119.68 (18)	C22—C17—C16	118.9 (2)
N1—C24—C23	118.42 (18)	C16—C15—C21^i	121.5 (2)
C25—C24—C23	121.90 (18)	C16—C15—H15	119.2
N2—C27—C26	119.64 (18)	C21^i—C15—H15	119.2
N2—C27—C28	118.54 (18)	C27—C28—H28A	109.5
C26—C27—C28	121.81 (19)	C27—C28—H28B	109.5
N1—C26—C27	122.63 (18)	H28A—C28—H28B	109.5
N1—C26—H26	118.7	C27—C28—H28C	109.5
C27—C26—H26	118.7	H28A—C28—H28C	109.5
O2—C2—C1	122.99 (18)	H28B—C28—H28C	109.5
O2—C2—C3	118.29 (18)	C19—C20—C21	120.6 (2)
C1—C2—C3	118.71 (19)	C19—C20—H20	119.7
C17—C22—C21	120.72 (19)	C21—C20—H20	119.7
C17—C22—C22^i	119.6 (2)	C10—C9—C14	118.8 (2)
C21—C22—C22^i	119.7 (2)	C10—C9—C8	122.6 (2)
C5—C4—C3	120.02 (18)	C14—C9—C8	118.6 (2)
C5—C4—H4	120.0	C15—C16—C17	121.5 (2)
C3—C4—H4	120.0	C15—C16—H16	119.3
O1—C6—C1	122.95 (18)	C17—C16—H16	119.3
O1—C6—C5	119.27 (18)	C20—C21—C22	118.6 (2)
C1—C6—C5	117.78 (19)	C20—C21—C15^i	122.5 (2)
C13—C14—C9	120.0 (2)	C22—C21—C15^i	118.84 (19)
C13—C14—C14^ii	120.4 (2)	C8—C7—C13^ii	121.7 (2)
C9—C14—C14^ii	119.6 (2)	C8—C7—H7	119.1
C4—C3—C2	120.07 (19)	C13^ii—C7—H7	119.1
C4—C3—Cl02	120.46 (16)	C11—C10—C9	121.1 (2)
C2—C3—Cl02	119.46 (16)	C11—C10—H10	119.5
C4—C5—C6	121.31 (19)	C9—C10—H10	119.5
C4—C5—Cl01	119.12 (16)	C20—C19—C18	120.8 (2)
C6—C5—Cl01	119.55 (17)	C20—C19—H19	119.6
N2—C25—C24	122.61 (18)	C18—C19—H19	119.6
N2—C25—H25	118.7	C19—C18—C17	120.9 (2)
C24—C25—H25	118.7	C19—C18—H18	119.5
C2—C1—C6	122.03 (19)	C17—C18—H18	119.5
C2—C1—H1A	119.0	C7—C8—C9	121.4 (2)
C6—C1—H1A	119.0	C7—C8—H8	119.3
C24—C23—H23A	109.5	C9—C8—H8	119.3
C24—C23—H23B	109.5	C11—C12—C13	120.9 (2)
H23A—C23—H23B	109.5	C11—C12—H12	119.5
C24—C23—H23C	109.5	C13—C12—H12	119.5
H23A—C23—H23C	109.5	C10—C11—C12	120.5 (2)
H23B—C23—H23C	109.5	C10—C11—H11	119.7
C12—C13—C14	118.7 (2)	C12—C11—H11	119.7

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z.

(32CRES-TMP-PHE-PYR)

Crystal data

C80H66Cl8N8O8	F(000) = 3208
Mr = 1551.00	Dx = 1.439 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71075 Å
a = 17.219 (5) Å	Cell parameters from 16938 reflections
b = 22.693 (7) Å	θ = 3.1–27.8°
c = 18.331 (5) Å	µ = 0.38 mm^−1
β = 91.312 (6)°	T = 150 K
V = 7161 (4) Å^3	Block, yellow
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	16751 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.107
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −22→22
Tmin = 0.453, Tmax = 1.000	k = −29→29
59375 measured reflections	l = −23→23
30424 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.123	w = 1/[σ^2(Fo^2) + (0.1617P)^2 + 25.0287P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.359	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.70 e Å^−3
30424 reflections	Δρmin = −0.66 e Å^−3
1889 parameters	Absolute structure: Flack x determined using 4452 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: 0.29 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl01	1.1263 (3)	0.28918 (18)	0.2565 (2)	0.0533 (11)
Cl02	0.7011 (3)	0.70734 (18)	0.6768 (3)	0.0537 (11)
Cl03	0.0865 (3)	0.74664 (17)	1.0546 (2)	0.0516 (10)
Cl04	0.5665 (3)	0.26764 (19)	0.3663 (2)	0.0565 (11)
Cl05	0.6340 (3)	0.74659 (18)	−0.1301 (2)	0.0540 (11)
Cl06	0.1375 (3)	0.73408 (19)	0.7646 (2)	0.0542 (11)
Cl07	0.6033 (3)	0.27509 (19)	1.1733 (2)	0.0547 (11)
Cl08	0.0983 (3)	0.26074 (19)	0.4477 (3)	0.0586 (12)
Cl09	1.1165 (3)	0.72645 (19)	0.2806 (3)	0.0558 (11)
Cl0A	0.1112 (3)	0.27331 (19)	0.7434 (3)	0.0594 (12)
Cl0B	0.6509 (3)	0.25345 (18)	0.6512 (2)	0.0546 (11)
Cl0C	1.1484 (3)	0.26634 (18)	−0.0362 (2)	0.0527 (11)
Cl0D	0.6127 (3)	0.74278 (19)	0.3957 (2)	0.0579 (12)
Cl0E	0.5468 (3)	0.7304 (2)	0.1518 (3)	0.0594 (12)
Cl0F	1.1660 (3)	0.73085 (19)	0.5721 (3)	0.0602 (12)
Cl0G	0.6869 (3)	0.27278 (19)	0.8911 (3)	0.0594 (12)
O00H	1.0265 (6)	0.6219 (4)	0.3114 (6)	0.043 (3)
H00H	0.999635	0.593196	0.321054	0.064*
O00I	0.5169 (6)	0.6373 (5)	0.4171 (6)	0.045 (3)
H00I	0.489699	0.608669	0.425989	0.067*
O00J	0.5923 (6)	0.6086 (5)	0.6695 (6)	0.044 (3)
H00J	0.563070	0.580190	0.665376	0.066*
O00K	0.7371 (7)	0.6470 (5)	−0.0916 (6)	0.048 (3)
H00K	0.765647	0.619853	−0.078548	0.071*
O00L	0.6615 (6)	0.6354 (5)	0.1607 (6)	0.043 (3)
H00L	0.694214	0.609116	0.160919	0.064*
O00M	0.1889 (6)	0.6455 (5)	1.0643 (6)	0.046 (3)
H00M	0.216945	0.616288	1.064427	0.069*
O00N	1.0615 (7)	0.6282 (5)	0.5725 (6)	0.053 (3)
H00N	1.033690	0.598907	0.570458	0.079*
O00O	1.0289 (7)	0.3895 (5)	0.2196 (5)	0.047 (3)
H00O	1.001202	0.417602	0.208305	0.070*
O00P	1.0462 (6)	0.3699 (4)	−0.0407 (6)	0.043 (3)
H00P	1.017748	0.398819	−0.040490	0.064*
N00Q	0.3035 (6)	0.5542 (5)	1.0630 (6)	0.028 (2)
O00R	0.6653 (6)	0.3733 (5)	0.3695 (6)	0.041 (2)
H00R	0.692787	0.402681	0.372649	0.062*
N00S	0.4193 (7)	0.5417 (5)	0.4492 (7)	0.033 (3)
O00T	0.5816 (7)	0.3739 (5)	0.8771 (6)	0.047 (3)
H00T	0.551519	0.401925	0.874789	0.070*
O00U	0.2113 (7)	0.3563 (5)	0.4566 (6)	0.050 (3)
H00U	0.243220	0.382918	0.461154	0.075*
N00V	0.8326 (7)	0.5555 (5)	−0.0494 (6)	0.032 (3)
N00W	0.3367 (7)	0.5404 (6)	0.8540 (7)	0.040 (3)
O00X	0.2283 (7)	0.6313 (5)	0.8059 (6)	0.052 (3)
H00X	0.254003	0.602806	0.819639	0.079*
O00Y	0.7378 (6)	0.3617 (5)	0.6243 (6)	0.046 (3)
H00Y	0.763883	0.390418	0.613010	0.069*
N00Z	0.9121 (8)	0.5415 (5)	0.3496 (7)	0.038 (3)
N010	0.4601 (8)	0.4590 (6)	0.8689 (6)	0.038 (3)
O011	0.5127 (7)	0.3792 (5)	1.1308 (6)	0.049 (3)
H011	0.486832	0.407511	1.116793	0.074*
O012	0.2231 (8)	0.3688 (5)	0.7181 (6)	0.057 (3)
H012	0.254222	0.394672	0.707759	0.086*
N013	0.9387 (7)	0.4663 (5)	−0.0315 (6)	0.034 (3)
N014	0.7844 (7)	0.4629 (5)	0.3729 (6)	0.033 (3)
N015	0.8375 (7)	0.4504 (5)	0.5877 (6)	0.034 (3)
N016	0.9478 (8)	0.5360 (6)	0.5635 (7)	0.042 (3)
N017	0.7883 (7)	0.5530 (6)	0.1625 (7)	0.039 (3)
N018	0.3153 (7)	0.4514 (5)	0.4723 (7)	0.036 (3)
N019	0.4671 (7)	0.5262 (6)	0.6652 (7)	0.037 (3)
C01A	0.1768 (9)	0.6641 (6)	0.9948 (8)	0.031 (3)
C01B	0.9089 (8)	0.5656 (6)	−0.0537 (7)	0.028 (3)
C01C	0.9634 (9)	0.5199 (7)	−0.0449 (8)	0.037 (3)
C01D	1.0739 (8)	0.6489 (6)	0.5023 (8)	0.032 (3)
C01E	1.0368 (8)	0.3803 (6)	0.0887 (8)	0.035 (3)
H01E	1.004580	0.412885	0.082045	0.042*
C01F	0.1202 (10)	0.7335 (6)	0.9106 (9)	0.045 (4)
H01F	0.089461	0.766540	0.901823	0.054*
C01G	0.8610 (8)	0.5722 (7)	0.1568 (8)	0.034 (3)
C01H	0.7754 (8)	0.5208 (6)	0.3584 (7)	0.030 (3)
C01I	0.8384 (9)	0.5605 (6)	0.3462 (7)	0.035 (3)
C01J	0.9255 (8)	0.5301 (6)	0.1631 (8)	0.032 (3)
N01K	0.4148 (7)	0.4692 (6)	1.0801 (7)	0.038 (3)
C01L	0.1410 (9)	0.2996 (6)	0.6590 (9)	0.041 (4)
C01M	0.5462 (9)	0.3768 (7)	1.0034 (8)	0.037 (3)
H01M	0.513202	0.408544	0.994284	0.045*
C01N	0.1936 (9)	0.3435 (6)	0.6549 (8)	0.033 (3)
C01O	0.6101 (8)	0.2690 (6)	0.5087 (8)	0.036 (3)
H01O	0.579572	0.235460	0.513691	0.044*
C01P	0.6976 (9)	0.4734 (6)	0.1837 (9)	0.038 (3)
H01P	0.655269	0.498167	0.175490	0.046*
C01Q	0.6982 (8)	0.3402 (6)	0.5626 (8)	0.034 (3)
N01R	0.9139 (7)	0.4735 (6)	0.1792 (7)	0.038 (3)
C01S	0.3437 (8)	0.5529 (6)	0.4472 (7)	0.031 (3)
N01T	0.3410 (7)	0.4504 (6)	0.6852 (7)	0.040 (3)
C01U	1.1367 (9)	0.7207 (6)	0.4273 (9)	0.043 (4)
H01U	1.169084	0.753341	0.423358	0.051*
C01V	0.5950 (8)	0.6379 (6)	0.6042 (8)	0.034 (3)
C01W	0.3798 (10)	0.6086 (7)	0.6447 (8)	0.043 (4)
H01W	0.420666	0.634823	0.638955	0.051*
C01X	1.0556 (9)	0.6449 (6)	0.3727 (8)	0.037 (3)
C01Y	0.4117 (9)	0.5570 (7)	0.8456 (8)	0.039 (4)
C01Z	0.6604 (9)	0.3484 (6)	0.4341 (8)	0.034 (3)
C020	0.8239 (11)	0.6210 (7)	0.3298 (9)	0.047 (4)
H020	0.865435	0.646239	0.321979	0.057*
C021	0.1977 (9)	0.4862 (8)	1.0777 (9)	0.044 (4)
H02B	0.170631	0.522125	1.087804	0.066*
H02C	0.188443	0.458153	1.115799	0.066*
H02D	0.179422	0.470426	1.031874	0.066*
C022	0.4745 (8)	0.5157 (7)	0.8581 (8)	0.034 (3)
C023	0.3345 (9)	0.5275 (7)	1.2613 (7)	0.037 (3)
C024	0.7004 (9)	0.6404 (6)	0.0350 (8)	0.036 (3)
H024	0.735249	0.609632	0.042775	0.043*
C025	0.6559 (9)	0.6597 (7)	0.0925 (9)	0.039 (4)
C026	0.4357 (9)	0.5232 (7)	1.0662 (8)	0.039 (3)
C027	1.0544 (9)	0.3631 (6)	0.1583 (8)	0.033 (3)
C028	0.3946 (8)	0.5474 (7)	0.6599 (8)	0.037 (3)
C029	0.6424 (8)	0.7143 (6)	−0.0441 (9)	0.038 (3)
C02A	0.1970 (9)	0.4973 (7)	1.2691 (8)	0.038 (3)
H02A	0.144379	0.506059	1.264680	0.045*
C02B	0.2174 (8)	0.3647 (7)	0.5873 (8)	0.039 (4)
H02J	0.252559	0.395753	0.585432	0.047*
C02C	0.7771 (9)	0.4948 (7)	0.1773 (8)	0.036 (3)
C02D	1.0038 (9)	0.5505 (7)	0.1544 (8)	0.040 (4)
H02H	1.045435	0.524523	0.158774	0.048*
C02E	0.9242 (9)	0.4838 (6)	0.3674 (8)	0.036 (3)
C02F	0.8706 (9)	0.5503 (6)	0.5596 (8)	0.035 (3)
C02G	0.4444 (8)	0.4848 (6)	0.4647 (7)	0.031 (3)
C02H	0.8760 (9)	0.6317 (8)	0.1424 (9)	0.045 (4)
H02I	0.835045	0.658222	0.137659	0.053*
C02I	0.3793 (9)	0.5673 (6)	1.0580 (8)	0.035 (3)
C02J	0.3849 (9)	0.4437 (6)	0.8744 (8)	0.034 (3)
C02K	0.4285 (8)	0.6207 (7)	0.8306 (9)	0.040 (4)
H02K	0.389383	0.648646	0.824912	0.048*
C02L	1.0421 (8)	0.6235 (6)	0.4400 (8)	0.036 (3)
H02L	1.010489	0.590525	0.444489	0.043*
C02M	0.1886 (9)	0.3393 (6)	0.5220 (8)	0.035 (3)
C02N	0.8606 (8)	0.4440 (6)	0.3775 (7)	0.031 (3)
C02O	0.6024 (8)	0.7052 (6)	0.0830 (9)	0.037 (3)
C02P	0.1979 (9)	0.6585 (6)	0.8642 (8)	0.037 (3)
C02Q	0.7023 (8)	0.3713 (7)	0.4957 (9)	0.039 (3)
H02Q	0.731525	0.405566	0.492136	0.047*
C02R	0.6974 (9)	0.5420 (8)	0.3529 (8)	0.041 (4)
H02R	0.655328	0.517103	0.360269	0.050*
C02S	0.8636 (8)	0.5735 (8)	0.7516 (8)	0.038 (3)
C02T	0.7612 (10)	0.5042 (7)	0.7728 (8)	0.044 (4)
H02T	0.708369	0.496801	0.777452	0.053*
C02U	0.9169 (8)	0.5273 (7)	0.7614 (7)	0.034 (3)
C02V	0.7313 (9)	0.5207 (8)	0.5699 (10)	0.049 (4)
H02E	0.702106	0.484884	0.574502	0.073*
H02F	0.718799	0.538839	0.523806	0.073*
H02G	0.718551	0.547086	0.608707	0.073*
C02W	0.6076 (9)	0.7006 (6)	0.4753 (9)	0.038 (3)
C02X	0.2529 (9)	0.5297 (8)	0.6623 (9)	0.045 (4)
H02X	0.211264	0.504378	0.669727	0.054*
C02Y	1.1035 (9)	0.6960 (6)	0.3649 (10)	0.043 (4)
C02Z	1.1225 (10)	0.6978 (6)	0.4947 (10)	0.049 (4)
C030	0.2911 (9)	0.5068 (7)	0.4596 (8)	0.039 (4)
C031	0.3224 (9)	0.4841 (7)	0.8684 (8)	0.037 (3)
C032	0.9664 (11)	0.6422 (8)	0.7288 (9)	0.052 (4)
H032	0.982106	0.680221	0.717302	0.062*
C033	0.2493 (10)	0.4637 (7)	0.8754 (9)	0.046 (4)
H033	0.208787	0.490654	0.870923	0.055*
C034	0.1306 (9)	0.7132 (7)	0.9820 (9)	0.041 (4)
C035	0.3320 (9)	0.5082 (7)	0.6675 (9)	0.042 (4)
C036	0.2062 (9)	0.5169 (9)	0.4576 (9)	0.049 (4)
H03B	0.179772	0.479712	0.453805	0.073*
H03C	0.192425	0.540926	0.416261	0.073*
H03D	0.191378	0.536470	0.501573	0.073*
C037	0.3646 (11)	0.6298 (7)	1.2335 (9)	0.048 (4)
H037	0.401109	0.659340	1.226816	0.057*
C038	0.9331 (11)	0.6290 (7)	−0.0674 (9)	0.046 (4)
H03M	0.952901	0.632358	−0.115768	0.069*
H03N	0.972696	0.640182	−0.032433	0.069*
H03O	0.888906	0.654386	−0.062753	0.069*
C039	0.7245 (8)	0.4887 (8)	−0.0315 (9)	0.043 (4)
H03P	0.697568	0.525362	−0.024952	0.065*
H03Q	0.714039	0.462955	0.008661	0.065*
H03R	0.706926	0.470647	−0.076215	0.065*
C03A	0.2875 (11)	0.6430 (7)	1.2280 (8)	0.044 (4)
H03A	0.272040	0.681164	1.216004	0.053*
C03B	0.8917 (9)	0.4697 (7)	0.7772 (8)	0.039 (4)
C03C	0.8499 (11)	0.6117 (7)	0.5417 (10)	0.054 (4)
H03T	0.896216	0.635213	0.540705	0.081*
H03V	0.815907	0.626866	0.577955	0.081*
H03W	0.824151	0.612944	0.494728	0.081*
C03D	0.9695 (8)	0.4821 (7)	0.5779 (7)	0.036 (3)
C03E	0.4786 (9)	0.4688 (7)	0.6795 (8)	0.038 (3)
C03F	0.3180 (11)	0.6140 (7)	0.4339 (9)	0.046 (4)
H03E	0.362464	0.639508	0.433296	0.070*
H03F	0.284122	0.626067	0.471914	0.070*
H03G	0.290773	0.616145	0.387656	0.070*
C03G	0.8170 (9)	0.5068 (8)	0.5740 (8)	0.040 (4)
C03H	0.2166 (9)	0.4429 (8)	1.2853 (9)	0.047 (4)
H03H	0.177986	0.415467	1.294566	0.057*
C03I	0.8898 (10)	0.6297 (9)	0.7351 (9)	0.053 (5)
H03I	0.853612	0.659736	0.728064	0.063*
C03J	0.5547 (8)	0.6211 (6)	0.5437 (8)	0.035 (3)
H03	0.524110	0.587418	0.545468	0.042*
C03K	0.8080 (9)	0.4998 (7)	−0.0343 (7)	0.034 (3)
C03L	0.4208 (11)	0.3788 (7)	0.4922 (10)	0.047 (4)
H03J	0.445560	0.378226	0.539639	0.070*
H03K	0.457387	0.366872	0.456272	0.070*
H03L	0.377484	0.352231	0.491363	0.070*
C03M	0.3906 (9)	0.5702 (8)	1.2498 (8)	0.042 (4)
C03N	0.6510 (9)	0.7160 (6)	0.5360 (10)	0.045 (4)
H0AA	0.684527	0.747965	0.532863	0.054*
C03O	1.0162 (10)	0.6102 (8)	0.1390 (9)	0.049 (4)
H03X	1.066432	0.623607	0.131278	0.059*
C03P	0.9523 (12)	0.6513 (9)	0.1351 (10)	0.059 (5)
H03Y	0.961989	0.691158	0.127729	0.071*
C03Q	0.6945 (9)	0.6657 (7)	−0.0337 (9)	0.043 (4)
C03R	0.1097 (9)	0.2740 (6)	0.5919 (11)	0.051 (5)
H2AA	0.073701	0.243535	0.594077	0.062*
C03S	0.5655 (11)	0.5967 (8)	0.8350 (9)	0.052 (4)
H03S	0.615980	0.610693	0.830910	0.062*
C03T	0.2138 (9)	0.6379 (7)	0.9346 (8)	0.037 (3)
H1AA	0.248621	0.606998	0.942009	0.045*
C03U	0.7834 (10)	0.5602 (8)	0.7575 (9)	0.047 (4)
H03U	0.746330	0.589590	0.750921	0.056*
C03V	0.5515 (9)	0.3556 (6)	1.0728 (8)	0.038 (3)
C03W	0.1531 (9)	0.7069 (7)	0.8552 (8)	0.037 (3)
C03X	0.8127 (9)	0.4569 (7)	0.7821 (8)	0.038 (3)
C03Y	0.5865 (10)	0.3542 (8)	0.9462 (9)	0.050 (4)
C03Z	0.3976 (10)	0.3517 (7)	1.3043 (9)	0.046 (4)
H03Z	0.412206	0.312958	1.313708	0.055*
C040	0.5569 (10)	0.4480 (7)	0.6850 (8)	0.040 (4)
H040	0.598484	0.473459	0.678413	0.048*
C041	0.6868 (9)	0.6003 (7)	0.3365 (10)	0.045 (4)
H041	0.636181	0.614244	0.331994	0.054*
C042	0.6413 (10)	0.2805 (8)	1.0321 (8)	0.046 (4)
H042	0.674142	0.248714	1.041769	0.055*
C043	1.0217 (10)	0.5976 (8)	0.7397 (9)	0.048 (4)
H043	1.074054	0.606433	0.734945	0.057*
C044	0.2844 (8)	0.4985 (6)	1.0741 (8)	0.034 (3)
C045	0.8409 (9)	0.4536 (6)	0.1858 (8)	0.036 (3)
C046	1.0297 (9)	0.4369 (8)	0.7843 (8)	0.044 (4)
H046	1.066966	0.407744	0.791846	0.053*
C047	0.4353 (10)	0.4535 (7)	1.2797 (8)	0.040 (4)
C048	0.5574 (12)	0.6531 (8)	0.4778 (9)	0.053 (5)
C049	0.4691 (11)	0.5539 (8)	1.2552 (9)	0.052 (4)
H049	0.506773	0.582800	1.249636	0.062*
C04A	1.0632 (10)	0.3531 (7)	0.0294 (9)	0.045 (4)
C04B	0.8432 (10)	0.3537 (7)	0.8116 (9)	0.046 (4)
H04B	0.826497	0.315512	0.820621	0.055*
C04C	0.4154 (9)	0.4290 (7)	0.6924 (8)	0.036 (3)
C04D	0.2496 (10)	0.5429 (8)	1.2582 (8)	0.045 (4)
C04E	0.5993 (10)	0.3056 (8)	1.0853 (9)	0.046 (4)
C04F	0.2324 (12)	0.6004 (7)	1.2399 (9)	0.053 (5)
H04F	0.180340	0.611014	1.235293	0.064*
C04G	0.3994 (10)	0.6316 (8)	1.0414 (11)	0.053 (5)
H04A	0.414609	0.634954	0.991564	0.079*
H04C	0.441369	0.644133	1.073089	0.079*
H04D	0.354731	0.655894	1.049266	0.079*
C04H	0.6881 (9)	0.4176 (7)	0.2017 (8)	0.040 (4)
H04P	0.637841	0.404324	0.209193	0.048*
C04I	0.5045 (13)	0.6344 (9)	0.8259 (10)	0.063 (5)
H04O	0.516395	0.673399	0.815409	0.076*
C04J	0.3394 (9)	0.4561 (6)	1.0848 (8)	0.035 (3)
C04K	0.3936 (10)	0.4384 (7)	0.4758 (8)	0.041 (4)
C04L	0.8613 (9)	0.4551 (6)	−0.0240 (7)	0.034 (3)
C04M	0.3189 (10)	0.3931 (7)	1.0972 (9)	0.048 (4)
H04E	0.299456	0.376150	1.052419	0.072*
H04G	0.279794	0.390662	1.133542	0.072*
H04H	0.364341	0.371955	1.113596	0.072*
C04N	0.6160 (8)	0.2964 (6)	0.4436 (8)	0.035 (3)
C04O	0.3550 (10)	0.4681 (7)	1.2762 (8)	0.038 (4)
C04P	0.6526 (11)	0.2934 (8)	0.5700 (9)	0.049 (4)
C04Q	0.2954 (11)	0.3626 (8)	0.8948 (10)	0.056 (5)
H04Q	0.284908	0.322858	0.902272	0.068*
C04R	0.6473 (8)	0.6867 (7)	0.6010 (10)	0.043 (4)
C04S	0.7890 (12)	0.3988 (8)	0.8000 (8)	0.050 (4)
H04S	0.736371	0.390651	0.804038	0.060*
C04T	0.3087 (11)	0.6264 (9)	0.6393 (10)	0.055 (5)
H04T	0.300640	0.666355	0.630533	0.066*
C04U	0.8347 (12)	0.3931 (8)	−0.0052 (9)	0.054 (5)
H04L	0.878241	0.366761	−0.005805	0.081*
H04M	0.796070	0.380375	−0.040363	0.081*
H04N	0.812844	0.393123	0.042558	0.081*
C04V	0.5304 (8)	0.4753 (8)	0.4649 (9)	0.044 (4)
H04I	0.543211	0.448456	0.426533	0.067*
H04J	0.547072	0.459147	0.511027	0.067*
H04K	0.556126	0.512276	0.457225	0.067*
C04W	0.7525 (9)	0.3750 (6)	0.2108 (9)	0.041 (4)
H04W	0.743124	0.335715	0.221881	0.049*
C04X	0.8250 (10)	0.3951 (7)	0.2023 (9)	0.043 (4)
H04X	0.866174	0.368883	0.207750	0.052*
C04Y	1.1331 (10)	0.2859 (7)	0.1066 (9)	0.044 (4)
H04Y	1.167375	0.254454	0.111684	0.052*
C04Z	1.1115 (9)	0.3038 (7)	0.0412 (9)	0.045 (4)
C050	0.5522 (9)	0.5351 (8)	0.8509 (9)	0.047 (4)
H050	0.593579	0.508943	0.856249	0.056*
C051	0.9486 (11)	0.3634 (9)	0.3964 (10)	0.055 (5)
H051	0.958252	0.323802	0.406163	0.066*
C052	0.5693 (12)	0.3875 (8)	0.7009 (8)	0.055 (5)
H052	0.619059	0.371593	0.703049	0.066*
C053	1.0471 (9)	0.5313 (8)	−0.0504 (9)	0.048 (4)
H05F	1.064570	0.554480	−0.009436	0.071*
H05G	1.056702	0.552283	−0.094760	0.071*
H05H	1.074697	0.494520	−0.050615	0.071*
C054	1.0567 (10)	0.4660 (8)	0.5800 (9)	0.048 (4)
H05I	1.069397	0.445409	0.536136	0.072*
H05J	1.067831	0.441299	0.621456	0.072*
H05N	1.087142	0.501390	0.583776	0.072*
C055	0.9489 (10)	0.4230 (7)	0.7906 (8)	0.042 (4)
C056	1.0138 (9)	0.4043 (8)	0.3863 (9)	0.047 (4)
H056	1.064384	0.389909	0.388917	0.056*
C057	0.7506 (11)	0.6421 (8)	0.3256 (10)	0.054 (5)
H057	0.740846	0.681744	0.316130	0.065*
C058	1.1048 (9)	0.3139 (6)	0.1693 (9)	0.042 (4)
C059	1.0524 (10)	0.4931 (8)	0.7673 (9)	0.048 (4)
H059	1.105110	0.500275	0.761959	0.057*
C05A	0.9144 (9)	0.4378 (6)	0.5897 (8)	0.036 (3)
C05B	0.4909 (10)	0.5005 (9)	1.2676 (10)	0.051 (4)
H05B	0.543662	0.491695	1.268914	0.061*
C05C	0.2400 (12)	0.5896 (10)	0.6457 (10)	0.064 (6)
H05S	0.190177	0.604824	0.639195	0.077*
C05D	0.9264 (12)	0.3670 (8)	0.8094 (9)	0.055 (5)
H05D	0.963170	0.338208	0.820469	0.066*
C05E	0.2971 (9)	0.4249 (8)	1.2889 (9)	0.044 (4)
C05F	1.0002 (10)	0.5408 (9)	0.7573 (9)	0.050 (4)
C05G	0.5218 (10)	0.5353 (8)	1.0631 (10)	0.052 (4)
H05A	0.550093	0.501161	1.079648	0.078*
H05C	0.534670	0.568212	1.093956	0.078*
H05E	0.535367	0.544136	1.013817	0.078*
C05H	0.9354 (10)	0.3732 (7)	0.6064 (9)	0.047 (4)
H05O	0.926653	0.365051	0.656885	0.070*
H05P	0.989158	0.366589	0.596063	0.070*
H05R	0.903625	0.347685	0.576493	0.070*
C05I	0.5968 (12)	0.7336 (8)	0.0083 (12)	0.072 (7)
H05V	0.561797	0.764106	−0.000797	0.086*
C05J	0.6333 (9)	0.3042 (7)	0.9622 (10)	0.045 (4)
C05K	0.8770 (9)	0.3826 (7)	0.3919 (10)	0.046 (4)
H05K	0.836166	0.356347	0.397967	0.056*
C05L	0.4543 (11)	0.3930 (7)	1.2929 (10)	0.052 (4)
H05L	0.506069	0.381376	1.293837	0.062*
C05M	0.3700 (10)	0.3827 (7)	0.8892 (9)	0.045 (4)
H05M	0.411381	0.356623	0.895038	0.054*
C05N	0.5051 (12)	0.3534 (8)	0.7128 (10)	0.058 (5)
H05T	0.514446	0.314247	0.725066	0.070*
C05O	0.4288 (11)	0.3703 (8)	0.7089 (9)	0.054 (4)
H05U	0.388426	0.343979	0.716740	0.064*
C05P	0.1325 (10)	0.2941 (6)	0.5265 (9)	0.043 (4)
C05Q	0.3179 (12)	0.3662 (8)	1.3021 (9)	0.055 (5)
H05Q	0.280236	0.337530	1.309165	0.065*
C1	1.0020 (9)	0.4613 (7)	0.3733 (9)	0.043 (4)
H1	1.044050	0.486521	0.368177	0.052*
C2	0.2313 (11)	0.4073 (10)	0.8882 (10)	0.064 (5)
H2	0.179757	0.395984	0.893060	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl01	0.062 (3)	0.041 (2)	0.056 (2)	0.0075 (19)	−0.017 (2)	0.0058 (18)
Cl02	0.051 (2)	0.042 (2)	0.067 (3)	0.0003 (18)	−0.020 (2)	−0.0086 (19)
Cl03	0.058 (3)	0.036 (2)	0.061 (3)	0.0112 (18)	0.013 (2)	−0.0052 (18)
Cl04	0.069 (3)	0.042 (2)	0.057 (2)	−0.014 (2)	−0.020 (2)	0.0040 (19)
Cl05	0.066 (3)	0.040 (2)	0.055 (2)	0.010 (2)	−0.012 (2)	0.0049 (18)
Cl06	0.066 (3)	0.046 (2)	0.050 (2)	−0.004 (2)	−0.011 (2)	0.0072 (19)
Cl07	0.070 (3)	0.044 (2)	0.050 (2)	0.005 (2)	−0.007 (2)	0.0057 (19)
Cl08	0.068 (3)	0.040 (2)	0.067 (3)	−0.007 (2)	−0.016 (2)	−0.001 (2)
Cl09	0.058 (3)	0.045 (2)	0.064 (3)	−0.005 (2)	0.009 (2)	0.021 (2)
Cl0A	0.064 (3)	0.045 (2)	0.070 (3)	−0.007 (2)	0.020 (2)	0.016 (2)
Cl0B	0.074 (3)	0.039 (2)	0.051 (2)	−0.010 (2)	−0.001 (2)	0.0125 (18)
Cl0C	0.057 (3)	0.039 (2)	0.064 (3)	0.0105 (19)	0.012 (2)	−0.0095 (19)
Cl0D	0.070 (3)	0.042 (2)	0.061 (3)	−0.014 (2)	0.000 (2)	0.019 (2)
Cl0E	0.061 (3)	0.046 (2)	0.071 (3)	0.016 (2)	0.010 (2)	−0.011 (2)
Cl0F	0.062 (3)	0.044 (2)	0.073 (3)	−0.014 (2)	−0.012 (2)	−0.011 (2)
Cl0G	0.061 (3)	0.044 (2)	0.075 (3)	0.011 (2)	0.029 (2)	−0.009 (2)
O00H	0.046 (6)	0.035 (6)	0.046 (6)	−0.013 (5)	0.005 (5)	0.011 (5)
O00I	0.037 (6)	0.045 (6)	0.053 (7)	−0.006 (5)	−0.002 (5)	0.017 (5)
O00J	0.043 (6)	0.041 (6)	0.048 (6)	−0.013 (5)	−0.002 (5)	0.005 (5)
O00K	0.057 (7)	0.034 (6)	0.051 (7)	0.011 (5)	−0.005 (6)	−0.004 (5)
O00L	0.048 (7)	0.036 (5)	0.046 (6)	0.019 (5)	0.003 (5)	0.005 (5)
O00M	0.031 (6)	0.048 (6)	0.060 (7)	0.016 (5)	0.006 (5)	−0.002 (6)
O00N	0.052 (7)	0.056 (7)	0.050 (7)	−0.034 (6)	0.001 (6)	−0.002 (6)
O00O	0.057 (7)	0.052 (7)	0.032 (6)	0.011 (6)	−0.006 (5)	0.001 (5)
O00P	0.050 (7)	0.031 (5)	0.047 (6)	0.014 (5)	0.003 (5)	−0.004 (5)
N00Q	0.022 (6)	0.033 (6)	0.028 (6)	−0.008 (5)	0.002 (5)	0.000 (5)
O00R	0.029 (5)	0.042 (6)	0.051 (7)	−0.007 (5)	−0.004 (5)	−0.005 (5)
N00S	0.025 (6)	0.028 (6)	0.045 (7)	−0.006 (5)	−0.006 (5)	−0.003 (5)
O00T	0.045 (6)	0.051 (7)	0.044 (6)	0.013 (5)	0.006 (5)	0.003 (5)
O00U	0.054 (7)	0.043 (6)	0.053 (7)	−0.019 (5)	−0.008 (6)	0.006 (5)
N00V	0.032 (6)	0.033 (6)	0.031 (6)	0.010 (5)	−0.005 (5)	−0.007 (5)
N00W	0.028 (7)	0.046 (8)	0.044 (7)	0.005 (6)	−0.012 (6)	−0.012 (6)
O00X	0.061 (8)	0.051 (7)	0.044 (7)	0.013 (6)	−0.007 (6)	−0.003 (5)
O00Y	0.044 (6)	0.043 (6)	0.052 (7)	−0.018 (5)	0.006 (5)	0.003 (5)
N00Z	0.048 (8)	0.033 (7)	0.033 (7)	−0.011 (6)	−0.002 (6)	0.006 (5)
N010	0.043 (8)	0.040 (7)	0.029 (6)	0.011 (6)	−0.004 (6)	−0.011 (5)
O011	0.058 (7)	0.044 (6)	0.046 (7)	0.012 (6)	0.000 (6)	0.005 (5)
O012	0.080 (9)	0.052 (7)	0.041 (7)	−0.020 (7)	0.013 (6)	−0.002 (5)
N013	0.037 (7)	0.039 (7)	0.027 (6)	0.013 (5)	−0.001 (5)	−0.009 (5)
N014	0.030 (6)	0.035 (6)	0.034 (7)	0.000 (5)	0.005 (5)	0.001 (5)
N015	0.038 (7)	0.036 (7)	0.029 (6)	0.004 (5)	0.010 (5)	−0.008 (5)
N016	0.041 (8)	0.036 (7)	0.048 (8)	−0.007 (6)	0.013 (6)	0.002 (6)
N017	0.032 (7)	0.049 (8)	0.036 (7)	0.002 (6)	−0.008 (5)	0.003 (6)
N018	0.033 (7)	0.038 (7)	0.036 (7)	−0.001 (5)	−0.003 (5)	−0.005 (5)
N019	0.032 (7)	0.046 (7)	0.033 (7)	−0.009 (6)	−0.002 (5)	0.002 (6)
C01A	0.037 (8)	0.021 (6)	0.036 (8)	−0.005 (6)	−0.007 (6)	0.002 (6)
C01B	0.028 (7)	0.024 (6)	0.033 (7)	−0.004 (5)	0.004 (6)	−0.008 (5)
C01C	0.042 (9)	0.039 (8)	0.030 (8)	−0.005 (7)	0.004 (6)	0.002 (6)
C01D	0.021 (7)	0.029 (7)	0.045 (8)	0.002 (5)	−0.002 (6)	0.001 (6)
C01E	0.023 (7)	0.035 (8)	0.047 (9)	0.004 (6)	−0.001 (6)	−0.004 (7)
C01F	0.054 (10)	0.022 (7)	0.059 (10)	−0.004 (7)	−0.005 (8)	0.003 (7)
C01G	0.022 (7)	0.050 (9)	0.030 (7)	−0.005 (6)	0.012 (6)	0.006 (6)
C01H	0.030 (7)	0.031 (7)	0.028 (7)	−0.011 (6)	0.000 (6)	0.006 (6)
C01I	0.045 (9)	0.032 (7)	0.027 (7)	−0.020 (7)	−0.007 (6)	0.003 (6)
C01J	0.034 (8)	0.023 (6)	0.040 (8)	−0.001 (6)	0.005 (6)	−0.008 (6)
N01K	0.031 (7)	0.043 (7)	0.041 (7)	0.006 (6)	−0.005 (6)	0.000 (6)
C01L	0.047 (9)	0.028 (7)	0.048 (9)	−0.008 (7)	0.012 (7)	−0.002 (7)
C01M	0.033 (8)	0.038 (8)	0.041 (9)	−0.008 (6)	−0.003 (7)	−0.006 (7)
C01N	0.040 (8)	0.019 (6)	0.041 (8)	−0.002 (6)	0.007 (7)	0.007 (6)
C01O	0.035 (8)	0.019 (6)	0.054 (9)	−0.011 (6)	−0.002 (7)	0.003 (6)
C01P	0.036 (8)	0.027 (7)	0.051 (9)	−0.003 (6)	0.004 (7)	0.009 (6)
C01Q	0.025 (7)	0.030 (7)	0.046 (9)	−0.006 (6)	−0.001 (6)	0.006 (6)
N01R	0.034 (7)	0.045 (7)	0.035 (7)	−0.002 (6)	0.002 (6)	−0.003 (6)
C01S	0.027 (7)	0.040 (8)	0.027 (7)	0.003 (6)	−0.001 (6)	−0.001 (6)
N01T	0.026 (6)	0.051 (8)	0.043 (7)	0.002 (6)	−0.003 (5)	−0.011 (6)
C01U	0.038 (8)	0.016 (6)	0.074 (11)	−0.008 (6)	−0.006 (8)	0.007 (7)
C01V	0.034 (8)	0.020 (6)	0.048 (9)	−0.004 (6)	0.004 (7)	−0.006 (6)
C01W	0.040 (9)	0.045 (9)	0.043 (9)	0.021 (7)	−0.002 (7)	0.000 (7)
C01X	0.036 (8)	0.033 (8)	0.042 (9)	0.009 (6)	−0.001 (7)	−0.005 (7)
C01Y	0.044 (9)	0.038 (8)	0.034 (8)	0.001 (7)	−0.009 (7)	−0.012 (6)
C01Z	0.041 (8)	0.027 (7)	0.035 (8)	0.009 (6)	−0.005 (6)	−0.005 (6)
C020	0.062 (12)	0.031 (8)	0.048 (10)	−0.009 (8)	0.000 (8)	−0.004 (7)
C021	0.039 (9)	0.058 (10)	0.034 (8)	−0.010 (8)	−0.003 (7)	−0.005 (7)
C022	0.024 (7)	0.046 (9)	0.033 (8)	−0.001 (6)	0.002 (6)	−0.010 (6)
C023	0.050 (9)	0.037 (8)	0.023 (7)	0.007 (7)	−0.004 (6)	−0.012 (6)
C024	0.044 (9)	0.016 (6)	0.047 (9)	0.015 (6)	−0.005 (7)	−0.005 (6)
C025	0.032 (8)	0.038 (8)	0.047 (9)	−0.006 (6)	0.000 (7)	−0.010 (7)
C026	0.031 (8)	0.044 (9)	0.040 (8)	0.001 (7)	−0.004 (6)	−0.004 (7)
C027	0.043 (8)	0.020 (6)	0.036 (8)	−0.003 (6)	0.002 (6)	−0.006 (6)
C028	0.025 (7)	0.042 (8)	0.043 (9)	−0.002 (6)	0.003 (6)	−0.001 (7)
C029	0.031 (8)	0.030 (7)	0.052 (9)	0.004 (6)	−0.009 (7)	−0.007 (7)
C02A	0.039 (8)	0.038 (8)	0.035 (8)	−0.005 (7)	−0.006 (7)	0.001 (6)
C02B	0.032 (8)	0.039 (8)	0.048 (9)	−0.022 (7)	0.003 (7)	−0.005 (7)
C02C	0.043 (9)	0.038 (8)	0.028 (8)	−0.003 (7)	0.007 (6)	0.000 (6)
C02D	0.032 (8)	0.052 (9)	0.036 (8)	−0.005 (7)	0.008 (6)	0.002 (7)
C02E	0.052 (9)	0.035 (7)	0.023 (7)	−0.020 (7)	0.007 (6)	−0.006 (6)
C02F	0.039 (8)	0.034 (7)	0.030 (8)	−0.002 (6)	0.004 (6)	−0.006 (6)
C02G	0.033 (8)	0.032 (7)	0.029 (7)	0.002 (6)	−0.001 (6)	0.004 (6)
C02H	0.029 (8)	0.061 (10)	0.044 (9)	0.003 (7)	0.009 (7)	0.006 (8)
C02I	0.037 (8)	0.036 (8)	0.033 (8)	0.010 (6)	0.008 (6)	−0.011 (6)
C02J	0.034 (8)	0.042 (8)	0.027 (7)	0.006 (6)	−0.007 (6)	−0.006 (6)
C02K	0.023 (7)	0.040 (8)	0.056 (10)	−0.005 (6)	0.001 (7)	−0.012 (7)
C02L	0.030 (8)	0.029 (7)	0.048 (9)	−0.004 (6)	0.003 (7)	0.009 (6)
C02M	0.038 (8)	0.028 (7)	0.038 (8)	0.004 (6)	−0.003 (7)	0.011 (6)
C02N	0.028 (7)	0.042 (8)	0.025 (7)	−0.007 (6)	0.003 (6)	0.004 (6)
C02O	0.024 (7)	0.033 (7)	0.053 (9)	−0.003 (6)	0.000 (7)	0.006 (7)
C02P	0.031 (8)	0.035 (8)	0.045 (9)	−0.007 (6)	−0.004 (7)	0.005 (7)
C02Q	0.028 (8)	0.041 (8)	0.049 (9)	−0.005 (6)	−0.001 (7)	−0.007 (7)
C02R	0.024 (7)	0.062 (10)	0.038 (8)	0.004 (7)	0.003 (6)	−0.012 (7)
C02S	0.026 (8)	0.057 (10)	0.031 (8)	−0.014 (7)	0.000 (6)	0.002 (7)
C02T	0.051 (10)	0.050 (9)	0.032 (9)	0.000 (8)	0.009 (7)	−0.004 (7)
C02U	0.032 (8)	0.047 (8)	0.023 (7)	−0.001 (6)	0.000 (6)	−0.010 (6)
C02V	0.039 (9)	0.056 (10)	0.050 (10)	0.019 (8)	0.000 (8)	−0.008 (8)
C02W	0.032 (8)	0.030 (7)	0.051 (9)	−0.006 (6)	0.006 (7)	0.004 (7)
C02X	0.032 (8)	0.053 (10)	0.049 (10)	−0.001 (7)	0.004 (7)	−0.013 (8)
C02Y	0.033 (8)	0.027 (7)	0.069 (11)	−0.007 (6)	−0.003 (8)	0.012 (7)
C02Z	0.056 (11)	0.018 (7)	0.072 (12)	−0.013 (7)	−0.010 (9)	0.002 (7)
C030	0.040 (9)	0.044 (8)	0.034 (8)	−0.011 (7)	0.009 (7)	−0.003 (7)
C031	0.034 (8)	0.046 (9)	0.029 (8)	0.000 (7)	0.004 (6)	−0.005 (6)
C032	0.066 (12)	0.038 (9)	0.051 (10)	−0.003 (8)	0.002 (9)	0.003 (8)
C033	0.039 (9)	0.042 (9)	0.056 (10)	0.004 (7)	−0.002 (8)	−0.006 (8)
C034	0.031 (8)	0.035 (8)	0.057 (10)	0.000 (6)	−0.008 (7)	0.002 (7)
C035	0.038 (9)	0.050 (9)	0.037 (9)	−0.004 (7)	−0.017 (7)	−0.009 (7)
C036	0.039 (9)	0.073 (12)	0.035 (9)	−0.016 (8)	0.001 (7)	−0.002 (8)
C037	0.064 (12)	0.037 (8)	0.043 (9)	−0.014 (8)	0.015 (8)	−0.003 (7)
C038	0.062 (11)	0.032 (8)	0.045 (9)	0.002 (7)	0.007 (8)	0.001 (7)
C039	0.027 (8)	0.053 (10)	0.049 (10)	0.004 (7)	−0.002 (7)	−0.007 (8)
C03A	0.061 (11)	0.040 (9)	0.033 (8)	−0.002 (8)	−0.001 (8)	−0.002 (7)
C03B	0.048 (9)	0.044 (9)	0.026 (7)	−0.005 (7)	0.009 (7)	−0.016 (6)
C03C	0.056 (11)	0.043 (9)	0.064 (12)	−0.006 (8)	0.003 (9)	0.006 (8)
C03D	0.031 (8)	0.053 (9)	0.023 (7)	−0.015 (7)	0.003 (6)	−0.006 (6)
C03E	0.032 (8)	0.044 (9)	0.036 (8)	0.015 (7)	0.002 (6)	−0.005 (7)
C03F	0.059 (11)	0.041 (9)	0.039 (9)	−0.003 (8)	−0.008 (8)	−0.007 (7)
C03G	0.035 (8)	0.054 (9)	0.030 (8)	0.008 (7)	0.003 (6)	−0.008 (7)
C03H	0.031 (9)	0.067 (12)	0.043 (9)	0.000 (8)	0.005 (7)	−0.010 (8)
C03I	0.035 (9)	0.070 (12)	0.053 (10)	0.016 (9)	−0.016 (8)	0.002 (9)
C03J	0.027 (7)	0.030 (7)	0.048 (9)	−0.003 (6)	0.007 (7)	0.016 (6)
C03K	0.044 (9)	0.043 (8)	0.016 (7)	0.011 (7)	−0.009 (6)	−0.009 (6)
C03L	0.057 (11)	0.027 (7)	0.056 (10)	0.005 (7)	0.004 (8)	0.001 (7)
C03M	0.037 (9)	0.063 (10)	0.026 (7)	0.000 (8)	−0.005 (6)	0.005 (7)
C03N	0.032 (8)	0.024 (7)	0.080 (12)	−0.008 (6)	−0.006 (8)	0.003 (7)
C03O	0.045 (10)	0.051 (10)	0.050 (10)	0.000 (8)	0.006 (8)	−0.006 (8)
C03P	0.061 (13)	0.062 (12)	0.053 (11)	−0.007 (10)	0.004 (9)	0.013 (9)
C03Q	0.040 (9)	0.037 (8)	0.051 (10)	−0.004 (7)	0.007 (7)	−0.016 (7)
C03R	0.029 (8)	0.021 (7)	0.103 (14)	0.006 (6)	0.005 (9)	−0.019 (9)
C03S	0.046 (10)	0.068 (12)	0.040 (9)	−0.017 (9)	−0.006 (8)	−0.009 (8)
C03T	0.044 (9)	0.040 (8)	0.028 (8)	0.004 (7)	−0.004 (7)	0.002 (6)
C03U	0.041 (9)	0.059 (11)	0.040 (9)	0.023 (8)	−0.007 (7)	−0.015 (8)
C03V	0.050 (9)	0.031 (7)	0.032 (8)	0.000 (7)	−0.011 (7)	−0.007 (6)
C03W	0.042 (9)	0.034 (7)	0.036 (8)	0.002 (7)	0.002 (7)	−0.003 (6)
C03X	0.049 (9)	0.037 (8)	0.027 (7)	0.004 (7)	0.000 (7)	−0.004 (6)
C03Y	0.049 (10)	0.057 (10)	0.042 (10)	0.010 (8)	−0.014 (8)	−0.023 (8)
C03Z	0.043 (9)	0.035 (8)	0.059 (10)	−0.002 (7)	0.000 (8)	−0.003 (7)
C040	0.045 (9)	0.040 (8)	0.034 (8)	−0.012 (7)	0.001 (7)	0.001 (7)
C041	0.026 (8)	0.032 (8)	0.076 (12)	0.002 (6)	−0.007 (8)	−0.003 (8)
C042	0.055 (10)	0.045 (9)	0.037 (9)	0.009 (8)	−0.001 (7)	−0.006 (7)
C043	0.046 (10)	0.052 (10)	0.045 (10)	−0.002 (8)	0.000 (8)	0.001 (8)
C044	0.028 (7)	0.031 (7)	0.044 (9)	0.001 (6)	−0.009 (6)	−0.004 (6)
C045	0.046 (9)	0.033 (7)	0.029 (7)	−0.007 (7)	0.005 (6)	−0.003 (6)
C046	0.036 (9)	0.063 (11)	0.034 (8)	0.000 (8)	−0.005 (7)	0.000 (7)
C047	0.052 (10)	0.036 (8)	0.033 (8)	−0.004 (7)	0.000 (7)	0.012 (6)
C048	0.079 (14)	0.049 (10)	0.031 (9)	−0.008 (9)	0.006 (9)	−0.003 (7)
C049	0.054 (11)	0.056 (11)	0.045 (10)	−0.008 (9)	0.009 (8)	0.005 (8)
C04A	0.046 (9)	0.039 (8)	0.049 (10)	0.013 (7)	−0.014 (8)	−0.013 (7)
C04B	0.057 (11)	0.030 (8)	0.051 (10)	−0.002 (7)	0.003 (8)	−0.001 (7)
C04C	0.034 (8)	0.039 (8)	0.036 (8)	−0.013 (6)	−0.004 (6)	0.003 (6)
C04D	0.046 (10)	0.055 (10)	0.032 (8)	−0.005 (8)	−0.004 (7)	−0.003 (7)
C04E	0.040 (9)	0.054 (10)	0.043 (9)	0.010 (8)	−0.004 (7)	0.007 (8)
C04F	0.077 (13)	0.042 (9)	0.041 (9)	0.023 (9)	−0.012 (9)	−0.008 (7)
C04G	0.031 (9)	0.053 (10)	0.075 (12)	−0.010 (8)	−0.010 (8)	0.016 (9)
C04H	0.028 (8)	0.047 (9)	0.044 (9)	0.016 (7)	−0.005 (7)	−0.010 (7)
C04I	0.079 (15)	0.064 (12)	0.046 (11)	−0.002 (11)	−0.003 (10)	−0.012 (9)
C04J	0.044 (9)	0.027 (7)	0.034 (8)	0.000 (6)	0.009 (7)	0.002 (6)
C04K	0.053 (10)	0.042 (9)	0.028 (8)	−0.010 (7)	−0.008 (7)	0.008 (6)
C04L	0.042 (9)	0.037 (8)	0.023 (7)	0.000 (6)	−0.008 (6)	−0.003 (6)
C04M	0.050 (10)	0.045 (9)	0.049 (10)	0.005 (8)	0.002 (8)	0.002 (8)
C04N	0.020 (7)	0.036 (8)	0.049 (9)	0.006 (6)	−0.003 (6)	−0.010 (7)
C04O	0.050 (10)	0.040 (8)	0.025 (7)	−0.018 (7)	0.013 (7)	−0.003 (6)
C04P	0.057 (11)	0.047 (9)	0.042 (9)	−0.010 (8)	−0.013 (8)	0.005 (7)
C04Q	0.062 (12)	0.045 (10)	0.063 (12)	0.002 (9)	0.008 (9)	−0.010 (9)
C04R	0.021 (7)	0.036 (8)	0.070 (11)	−0.003 (6)	−0.012 (7)	−0.007 (8)
C04S	0.067 (12)	0.055 (10)	0.029 (8)	0.001 (9)	0.002 (8)	−0.002 (7)
C04T	0.059 (12)	0.057 (11)	0.049 (10)	0.013 (9)	−0.010 (9)	0.002 (8)
C04U	0.073 (13)	0.047 (10)	0.042 (10)	0.005 (9)	−0.010 (9)	−0.007 (8)
C04V	0.025 (8)	0.054 (10)	0.055 (10)	−0.005 (7)	−0.004 (7)	0.005 (8)
C04W	0.032 (8)	0.028 (7)	0.061 (10)	0.013 (6)	−0.015 (7)	0.000 (7)
C04X	0.040 (9)	0.037 (8)	0.053 (10)	0.007 (7)	0.001 (7)	−0.010 (7)
C04Y	0.047 (9)	0.036 (8)	0.048 (9)	−0.002 (7)	0.003 (8)	−0.016 (7)
C04Z	0.038 (9)	0.038 (8)	0.058 (11)	0.017 (7)	−0.005 (8)	−0.032 (8)
C050	0.034 (9)	0.053 (10)	0.053 (10)	0.003 (7)	−0.006 (7)	−0.003 (8)
C051	0.054 (11)	0.059 (11)	0.053 (11)	−0.014 (9)	0.011 (9)	0.012 (9)
C052	0.078 (13)	0.061 (11)	0.026 (8)	0.011 (10)	0.008 (8)	−0.007 (8)
C053	0.027 (8)	0.067 (11)	0.048 (10)	0.010 (8)	−0.013 (7)	−0.009 (8)
C054	0.045 (10)	0.053 (10)	0.047 (10)	0.002 (8)	0.004 (8)	−0.011 (8)
C055	0.044 (9)	0.052 (9)	0.029 (8)	0.015 (8)	0.007 (7)	−0.005 (7)
C056	0.029 (8)	0.055 (10)	0.056 (10)	0.007 (7)	−0.003 (7)	−0.003 (8)
C057	0.062 (12)	0.043 (9)	0.057 (11)	−0.009 (9)	−0.008 (9)	0.002 (8)
C058	0.043 (9)	0.028 (7)	0.056 (10)	−0.003 (6)	−0.015 (8)	−0.010 (7)
C059	0.041 (9)	0.062 (11)	0.040 (9)	0.006 (8)	0.000 (7)	−0.005 (8)
C05A	0.033 (8)	0.032 (8)	0.041 (8)	−0.008 (6)	−0.004 (7)	0.002 (6)
C05B	0.034 (9)	0.068 (12)	0.053 (11)	0.003 (8)	0.003 (8)	−0.004 (9)
C05C	0.065 (13)	0.083 (15)	0.045 (11)	0.008 (11)	0.010 (9)	−0.031 (10)
C05D	0.072 (13)	0.048 (10)	0.045 (10)	−0.009 (9)	0.007 (9)	−0.010 (8)
C05E	0.031 (8)	0.057 (10)	0.042 (9)	−0.006 (7)	−0.009 (7)	−0.008 (8)
C05F	0.039 (9)	0.074 (13)	0.037 (9)	0.000 (9)	−0.003 (7)	−0.010 (8)
C05G	0.039 (9)	0.051 (10)	0.065 (12)	0.001 (8)	−0.003 (8)	−0.007 (9)
C05H	0.051 (10)	0.035 (8)	0.053 (10)	0.006 (7)	−0.011 (8)	−0.005 (7)
C05I	0.063 (12)	0.038 (9)	0.112 (17)	0.017 (9)	−0.042 (12)	−0.040 (11)
C05J	0.039 (9)	0.028 (8)	0.067 (11)	−0.001 (6)	0.021 (8)	−0.023 (7)
C05K	0.029 (8)	0.042 (9)	0.068 (11)	0.012 (7)	0.005 (8)	0.016 (8)
C05L	0.053 (11)	0.045 (9)	0.058 (11)	0.023 (8)	0.004 (9)	0.006 (8)
C05M	0.045 (10)	0.042 (9)	0.047 (10)	−0.004 (7)	0.006 (8)	−0.001 (7)
C05N	0.069 (13)	0.043 (10)	0.064 (12)	0.001 (9)	0.022 (10)	0.007 (9)
C05O	0.060 (12)	0.054 (11)	0.046 (10)	−0.010 (9)	0.000 (9)	−0.007 (8)
C05P	0.061 (11)	0.014 (6)	0.053 (10)	−0.002 (7)	0.006 (8)	0.000 (6)
C05Q	0.068 (13)	0.049 (10)	0.047 (10)	0.001 (9)	0.002 (9)	−0.005 (8)
C1	0.036 (9)	0.045 (9)	0.049 (10)	−0.003 (7)	0.004 (7)	−0.001 (7)
C2	0.042 (11)	0.089 (15)	0.060 (12)	−0.014 (10)	−0.004 (9)	−0.007 (11)

Geometric parameters (Å, º)

Cl01—C058	1.727 (17)	C02R—C041	1.37 (2)
Cl02—C04R	1.718 (16)	C02R—H02R	0.9300
Cl03—C034	1.723 (17)	C02S—C03I	1.39 (2)
Cl04—C04N	1.762 (15)	C02S—C02U	1.40 (2)
Cl05—C029	1.741 (16)	C02S—C03U	1.42 (2)
Cl06—C03W	1.787 (15)	C02T—C03U	1.36 (2)
Cl07—C04E	1.755 (17)	C02T—C03X	1.40 (2)
Cl08—C05P	1.722 (16)	C02T—H02T	0.9300
Cl09—C02Y	1.713 (17)	C02U—C03B	1.41 (2)
Cl0A—C01L	1.747 (16)	C02U—C05F	1.47 (2)
Cl0B—C04P	1.744 (17)	C02V—C03G	1.51 (2)
Cl0C—C04Z	1.783 (15)	C02V—H02E	0.9600
Cl0D—C02W	1.748 (16)	C02V—H02F	0.9600
Cl0E—C02O	1.701 (16)	C02V—H02G	0.9600
Cl0F—C02Z	1.758 (17)	C02W—C03N	1.37 (2)
Cl0G—C05J	1.763 (15)	C02W—C048	1.38 (2)
O00H—C01X	1.328 (18)	C02X—C05C	1.41 (3)
O00H—H00H	0.8200	C02X—C035	1.45 (2)
O00I—C048	1.35 (2)	C02X—H02X	0.9300
O00I—H00I	0.8200	C030—C036	1.48 (2)
O00J—C01V	1.371 (18)	C031—C033	1.35 (2)
O00J—H00J	0.8200	C032—C03I	1.36 (3)
O00K—C03Q	1.373 (19)	C032—C043	1.40 (2)
O00K—H00K	0.8200	C032—H032	0.9300
O00L—C025	1.367 (19)	C033—C2	1.34 (3)
O00L—H00L	0.8200	C033—H033	0.9300
O00M—C01A	1.354 (17)	C036—H03B	0.9600
O00M—H00M	0.8200	C036—H03C	0.9600
O00N—C01D	1.391 (18)	C036—H03D	0.9600
O00N—H00N	0.8200	C037—C03A	1.36 (2)
O00O—C027	1.355 (17)	C037—C03M	1.45 (2)
O00O—H00O	0.8200	C037—H037	0.9300
O00P—C04A	1.365 (19)	C038—H03M	0.9600
O00P—H00P	0.8200	C038—H03N	0.9600
N00Q—C044	1.323 (18)	C038—H03O	0.9600
N00Q—C02I	1.344 (18)	C039—C03K	1.46 (2)
O00R—C01Z	1.317 (18)	C039—H03P	0.9600
O00R—H00R	0.8200	C039—H03Q	0.9600
N00S—C01S	1.326 (18)	C039—H03R	0.9600
N00S—C02G	1.388 (17)	C03A—C04F	1.38 (3)
O00T—C03Y	1.34 (2)	C03A—H03A	0.9300
O00T—H00T	0.8200	C03B—C03X	1.40 (2)
O00U—C02M	1.326 (18)	C03B—C055	1.46 (2)
O00U—H00U	0.8200	C03C—H03T	0.9600
N00V—C01B	1.338 (18)	C03C—H03V	0.9600
N00V—C03K	1.364 (19)	C03C—H03W	0.9600
N00W—C031	1.33 (2)	C03D—C05A	1.40 (2)
N00W—C01Y	1.36 (2)	C03D—C054	1.55 (2)
O00X—C02P	1.350 (19)	C03E—C040	1.43 (2)
O00X—H00X	0.8200	C03E—C04C	1.44 (2)
O00Y—C01Q	1.397 (18)	C03F—H03E	0.9600
O00Y—H00Y	0.8200	C03F—H03F	0.9600
N00Z—C01I	1.34 (2)	C03F—H03G	0.9600
N00Z—C02E	1.366 (19)	C03H—C05E	1.45 (2)
N010—C022	1.325 (19)	C03H—H03H	0.9300
N010—C02J	1.34 (2)	C03I—H03I	0.9300
O011—C03V	1.375 (19)	C03J—C048	1.41 (2)
O011—H011	0.8200	C03J—H03	0.9300
O012—C01N	1.380 (18)	C03K—C04L	1.38 (2)
O012—H012	0.8200	C03L—C04K	1.46 (2)
N013—C01C	1.313 (19)	C03L—H03J	0.9600
N013—C04L	1.367 (19)	C03L—H03K	0.9600
N014—C01H	1.349 (18)	C03L—H03L	0.9600
N014—C02N	1.380 (18)	C03M—C049	1.40 (2)
N015—C03G	1.35 (2)	C03N—C04R	1.37 (2)
N015—C05A	1.355 (19)	C03N—H0AA	0.9300
N016—C03D	1.31 (2)	C03O—C03P	1.44 (3)
N016—C02F	1.37 (2)	C03O—H03X	0.9300
N017—C01G	1.330 (18)	C03P—H03Y	0.9300
N017—C02C	1.36 (2)	C03R—C05P	1.35 (2)
N018—C030	1.34 (2)	C03R—H2AA	0.9300
N018—C04K	1.38 (2)	C03S—C04I	1.36 (3)
N019—C028	1.340 (19)	C03S—C050	1.45 (2)
N019—C03E	1.34 (2)	C03S—H03S	0.9300
C01A—C034	1.39 (2)	C03T—H1AA	0.9300
C01A—C03T	1.42 (2)	C03U—H03U	0.9300
C01B—C01C	1.41 (2)	C03V—C04E	1.42 (2)
C01B—C038	1.520 (19)	C03X—C04S	1.42 (2)
C01C—C053	1.47 (2)	C03Y—C05J	1.42 (2)
C01D—C02L	1.38 (2)	C03Z—C05L	1.37 (2)
C01D—C02Z	1.40 (2)	C03Z—C05Q	1.41 (3)
C01E—C04A	1.34 (2)	C03Z—H03Z	0.9300
C01E—C027	1.36 (2)	C040—C052	1.42 (2)
C01E—H01E	0.9300	C040—H040	0.9300
C01F—C03W	1.32 (2)	C041—C057	1.47 (2)
C01F—C034	1.39 (2)	C041—H041	0.9300
C01F—H01F	0.9300	C042—C04E	1.35 (2)
C01G—C02H	1.40 (2)	C042—C05J	1.39 (2)
C01G—C01J	1.47 (2)	C042—H042	0.9300
C01H—C02R	1.43 (2)	C043—C05F	1.38 (2)
C01H—C01I	1.432 (18)	C043—H043	0.9300
C01I—C020	1.43 (2)	C044—C04J	1.36 (2)
C01J—N01R	1.333 (18)	C045—C04X	1.39 (2)
C01J—C02D	1.44 (2)	C046—C059	1.37 (2)
N01K—C026	1.30 (2)	C046—C055	1.43 (2)
N01K—C04J	1.336 (19)	C046—H046	0.9300
C01L—C01N	1.35 (2)	C047—C04O	1.42 (2)
C01L—C03R	1.45 (2)	C047—C05L	1.43 (2)
C01M—C03V	1.36 (2)	C047—C05B	1.45 (2)
C01M—C03Y	1.37 (2)	C049—C05B	1.29 (3)
C01M—H01M	0.9300	C049—H049	0.9300
C01N—C02B	1.40 (2)	C04A—C04Z	1.41 (2)
C01O—C04N	1.35 (2)	C04B—C04S	1.40 (2)
C01O—C04P	1.44 (2)	C04B—C05D	1.47 (3)
C01O—H01O	0.9300	C04B—H04B	0.9300
C01P—C04H	1.32 (2)	C04C—C05O	1.38 (2)
C01P—C02C	1.46 (2)	C04D—C04F	1.38 (2)
C01P—H01P	0.9300	C04F—H04F	0.9300
C01Q—C04P	1.33 (2)	C04G—H04A	0.9600
C01Q—C02Q	1.42 (2)	C04G—H04C	0.9600
N01R—C045	1.344 (19)	C04G—H04D	0.9600
C01S—C030	1.40 (2)	C04H—C04W	1.478 (18)
C01S—C03F	1.47 (2)	C04H—H04P	0.9300
N01T—C035	1.36 (2)	C04I—H04O	0.9300
N01T—C04C	1.37 (2)	C04J—C04M	1.49 (2)
C01U—C02Z	1.37 (2)	C04L—C04U	1.52 (2)
C01U—C02Y	1.39 (2)	C04M—H04E	0.9600
C01U—H01U	0.9300	C04M—H04G	0.9600
C01V—C03J	1.35 (2)	C04M—H04H	0.9600
C01V—C04R	1.43 (2)	C04O—C05E	1.42 (2)
C01W—C04T	1.29 (2)	C04Q—C05M	1.37 (2)
C01W—C028	1.44 (2)	C04Q—C2	1.50 (3)
C01W—H01W	0.9300	C04Q—H04Q	0.9300
C01X—C02L	1.35 (2)	C04S—H04S	0.9300
C01X—C02Y	1.43 (2)	C04T—C05C	1.45 (3)
C01Y—C022	1.45 (2)	C04T—H04T	0.9300
C01Y—C02K	1.50 (2)	C04U—H04L	0.9600
C01Z—C04N	1.42 (2)	C04U—H04M	0.9600
C01Z—C02Q	1.42 (2)	C04U—H04N	0.9600
C020—C057	1.35 (3)	C04V—H04I	0.9600
C020—H020	0.9300	C04V—H04J	0.9600
C021—C044	1.52 (2)	C04V—H04K	0.9600
C021—H02B	0.9600	C04W—C04X	1.34 (2)
C021—H02C	0.9600	C04W—H04W	0.9300
C021—H02D	0.9600	C04X—H04X	0.9300
C022—C050	1.42 (2)	C04Y—C04Z	1.31 (2)
C023—C03M	1.39 (2)	C04Y—C058	1.41 (2)
C023—C04O	1.42 (2)	C04Y—H04Y	0.9300
C023—C04D	1.50 (2)	C050—H050	0.9300
C024—C03Q	1.38 (2)	C051—C05K	1.31 (2)
C024—C025	1.39 (2)	C051—C056	1.47 (2)
C024—H024	0.9300	C051—H051	0.9300
C025—C02O	1.39 (2)	C052—C05N	1.37 (3)
C026—C02I	1.40 (2)	C052—H052	0.9300
C026—C05G	1.51 (2)	C053—H05F	0.9600
C027—C058	1.43 (2)	C053—H05G	0.9600
C028—C035	1.41 (2)	C053—H05H	0.9600
C029—C05I	1.33 (3)	C054—H05I	0.9600
C029—C03Q	1.43 (2)	C054—H05J	0.9600
C02A—C03H	1.31 (2)	C054—H05N	0.9600
C02A—C04D	1.39 (2)	C055—C05D	1.37 (2)
C02A—H02A	0.9300	C056—C1	1.33 (2)
C02B—C02M	1.41 (2)	C056—H056	0.9300
C02B—H02J	0.9300	C057—H057	0.9300
C02C—C045	1.45 (2)	C059—C05F	1.42 (2)
C02D—C03O	1.40 (2)	C059—H059	0.9300
C02D—H02H	0.9300	C05A—C05H	1.54 (2)
C02E—C02N	1.435 (19)	C05B—H05B	0.9300
C02E—C1	1.44 (2)	C05C—H05S	0.9300
C02F—C03G	1.38 (2)	C05D—H05D	0.9300
C02F—C03C	1.47 (2)	C05E—C05Q	1.40 (2)
C02G—C04K	1.39 (2)	C05G—H05A	0.9600
C02G—C04V	1.50 (2)	C05G—H05C	0.9600
C02H—C03P	1.40 (2)	C05G—H05E	0.9600
C02H—H02I	0.9300	C05H—H05O	0.9600
C02I—C04G	1.53 (2)	C05H—H05P	0.9600
C02J—C031	1.42 (2)	C05H—H05R	0.9600
C02J—C05M	1.44 (2)	C05I—H05V	0.9300
C02K—C04I	1.35 (3)	C05K—H05K	0.9300
C02K—H02K	0.9300	C05L—H05L	0.9300
C02L—H02L	0.9300	C05M—H05M	0.9300
C02M—C05P	1.41 (2)	C05N—C05O	1.37 (3)
C02N—C05K	1.45 (2)	C05N—H05T	0.9300
C02O—C05I	1.51 (3)	C05O—H05U	0.9300
C02P—C03W	1.35 (2)	C05Q—H05Q	0.9300
C02P—C03T	1.39 (2)	C1—H1	0.9300
C02Q—H02Q	0.9300	C2—H2	0.9300
C01X—O00H—H00H	109.5	C02F—C03G—C02V	119.9 (15)
C048—O00I—H00I	109.5	C02A—C03H—C05E	121.2 (17)
C01V—O00J—H00J	109.5	C02A—C03H—H03H	119.4
C03Q—O00K—H00K	109.5	C05E—C03H—H03H	119.4
C025—O00L—H00L	109.5	C032—C03I—C02S	122.1 (16)
C01A—O00M—H00M	109.5	C032—C03I—H03I	118.9
C01D—O00N—H00N	109.5	C02S—C03I—H03I	118.9
C027—O00O—H00O	109.5	C01V—C03J—C048	122.2 (14)
C04A—O00P—H00P	109.5	C01V—C03J—H03	118.9
C044—N00Q—C02I	117.9 (12)	C048—C03J—H03	118.9
C01Z—O00R—H00R	109.5	N00V—C03K—C04L	120.1 (14)
C01S—N00S—C02G	118.9 (12)	N00V—C03K—C039	118.5 (13)
C03Y—O00T—H00T	109.5	C04L—C03K—C039	121.4 (15)
C02M—O00U—H00U	109.5	C04K—C03L—H03J	109.5
C01B—N00V—C03K	118.7 (12)	C04K—C03L—H03K	109.5
C031—N00W—C01Y	117.9 (13)	H03J—C03L—H03K	109.5
C02P—O00X—H00X	109.5	C04K—C03L—H03L	109.5
C01Q—O00Y—H00Y	109.5	H03J—C03L—H03L	109.5
C01I—N00Z—C02E	117.3 (13)	H03K—C03L—H03L	109.5
C022—N010—C02J	116.4 (13)	C023—C03M—C049	118.6 (16)
C03V—O011—H011	109.5	C023—C03M—C037	117.9 (15)
C01N—O012—H012	109.5	C049—C03M—C037	123.5 (16)
C01C—N013—C04L	120.9 (13)	C04R—C03N—C02W	123.2 (14)
C01H—N014—C02N	114.8 (12)	C04R—C03N—H0AA	118.4
C03G—N015—C05A	117.1 (13)	C02W—C03N—H0AA	118.4
C03D—N016—C02F	120.4 (13)	C02D—C03O—C03P	121.0 (16)
C01G—N017—C02C	118.0 (13)	C02D—C03O—H03X	119.5
C030—N018—C04K	120.4 (13)	C03P—C03O—H03X	119.5
C028—N019—C03E	119.8 (13)	C02H—C03P—C03O	120.5 (17)
O00M—C01A—C034	119.0 (14)	C02H—C03P—H03Y	119.7
O00M—C01A—C03T	122.7 (12)	C03O—C03P—H03Y	119.7
C034—C01A—C03T	118.2 (13)	O00K—C03Q—C024	123.0 (14)
N00V—C01B—C01C	121.5 (12)	O00K—C03Q—C029	118.6 (15)
N00V—C01B—C038	116.4 (13)	C024—C03Q—C029	118.3 (14)
C01C—C01B—C038	122.2 (13)	C05P—C03R—C01L	120.5 (14)
N013—C01C—C01B	119.1 (14)	C05P—C03R—H2AA	119.7
N013—C01C—C053	119.9 (15)	C01L—C03R—H2AA	119.7
C01B—C01C—C053	121.0 (14)	C04I—C03S—C050	120.4 (17)
C02L—C01D—O00N	123.9 (12)	C04I—C03S—H03S	119.8
C02L—C01D—C02Z	118.4 (14)	C050—C03S—H03S	119.8
O00N—C01D—C02Z	117.7 (13)	C02P—C03T—C01A	119.8 (14)
C04A—C01E—C027	123.7 (14)	C02P—C03T—H1AA	120.1
C04A—C01E—H01E	118.1	C01A—C03T—H1AA	120.1
C027—C01E—H01E	118.1	C02T—C03U—C02S	119.7 (15)
C03W—C01F—C034	121.5 (15)	C02T—C03U—H03U	120.2
C03W—C01F—H01F	119.3	C02S—C03U—H03U	120.2
C034—C01F—H01F	119.3	C01M—C03V—O011	124.1 (14)
N017—C01G—C02H	120.5 (14)	C01M—C03V—C04E	117.4 (15)
N017—C01G—C01J	119.5 (13)	O011—C03V—C04E	118.5 (13)
C02H—C01G—C01J	119.9 (12)	C01F—C03W—C02P	122.2 (15)
N014—C01H—C02R	116.5 (13)	C01F—C03W—Cl06	119.9 (12)
N014—C01H—C01I	124.1 (13)	C02P—C03W—Cl06	117.9 (12)
C02R—C01H—C01I	119.4 (13)	C03B—C03X—C02T	116.6 (15)
N00Z—C01I—C020	118.7 (14)	C03B—C03X—C04S	119.6 (15)
N00Z—C01I—C01H	120.7 (13)	C02T—C03X—C04S	123.7 (16)
C020—C01I—C01H	120.7 (15)	O00T—C03Y—C01M	125.0 (15)
N01R—C01J—C02D	118.7 (14)	O00T—C03Y—C05J	118.9 (14)
N01R—C01J—C01G	121.8 (13)	C01M—C03Y—C05J	115.9 (16)
C02D—C01J—C01G	119.5 (13)	C05L—C03Z—C05Q	122.1 (16)
C026—N01K—C04J	119.6 (13)	C05L—C03Z—H03Z	118.9
C01N—C01L—C03R	119.0 (14)	C05Q—C03Z—H03Z	118.9
C01N—C01L—Cl0A	120.8 (13)	C052—C040—C03E	118.1 (16)
C03R—C01L—Cl0A	120.2 (12)	C052—C040—H040	120.9
C03V—C01M—C03Y	124.0 (15)	C03E—C040—H040	120.9
C03V—C01M—H01M	118.0	C02R—C041—C057	124.0 (15)
C03Y—C01M—H01M	118.0	C02R—C041—H041	118.0
C01L—C01N—O012	119.7 (13)	C057—C041—H041	118.0
C01L—C01N—C02B	120.9 (14)	C04E—C042—C05J	117.1 (15)
O012—C01N—C02B	119.4 (12)	C04E—C042—H042	121.4
C04N—C01O—C04P	117.7 (13)	C05J—C042—H042	121.4
C04N—C01O—H01O	121.2	C05F—C043—C032	121.5 (17)
C04P—C01O—H01O	121.2	C05F—C043—H043	119.2
C04H—C01P—C02C	117.5 (14)	C032—C043—H043	119.2
C04H—C01P—H01P	121.3	N00Q—C044—C04J	121.5 (13)
C02C—C01P—H01P	121.3	N00Q—C044—C021	115.5 (13)
C04P—C01Q—O00Y	118.4 (13)	C04J—C044—C021	123.0 (14)
C04P—C01Q—C02Q	121.8 (14)	N01R—C045—C04X	122.1 (15)
O00Y—C01Q—C02Q	119.6 (12)	N01R—C045—C02C	118.8 (13)
C01J—N01R—C045	119.3 (13)	C04X—C045—C02C	119.1 (14)
N00S—C01S—C030	119.3 (13)	C059—C046—C055	120.3 (16)
N00S—C01S—C03F	118.3 (14)	C059—C046—H046	119.8
C030—C01S—C03F	122.3 (14)	C055—C046—H046	119.8
C035—N01T—C04C	117.7 (13)	C04O—C047—C05L	116.6 (15)
C02Z—C01U—C02Y	120.7 (13)	C04O—C047—C05B	117.9 (14)
C02Z—C01U—H01U	119.6	C05L—C047—C05B	125.5 (16)
C02Y—C01U—H01U	119.6	O00I—C048—C02W	119.4 (15)
C03J—C01V—O00J	123.6 (12)	O00I—C048—C03J	123.0 (15)
C03J—C01V—C04R	119.8 (14)	C02W—C048—C03J	117.5 (15)
O00J—C01V—C04R	116.5 (13)	C05B—C049—C03M	122.5 (18)
C04T—C01W—C028	118.8 (17)	C05B—C049—H049	118.8
C04T—C01W—H01W	120.6	C03M—C049—H049	118.8
C028—C01W—H01W	120.6	C01E—C04A—O00P	124.6 (14)
O00H—C01X—C02L	124.2 (14)	C01E—C04A—C04Z	116.9 (15)
O00H—C01X—C02Y	116.2 (14)	O00P—C04A—C04Z	118.5 (14)
C02L—C01X—C02Y	119.6 (14)	C04S—C04B—C05D	119.6 (16)
N00W—C01Y—C022	120.9 (14)	C04S—C04B—H04B	120.2
N00W—C01Y—C02K	118.4 (14)	C05D—C04B—H04B	120.2
C022—C01Y—C02K	120.5 (14)	N01T—C04C—C05O	120.7 (15)
O00R—C01Z—C04N	120.8 (13)	N01T—C04C—C03E	118.1 (13)
O00R—C01Z—C02Q	121.1 (14)	C05O—C04C—C03E	121.2 (15)
C04N—C01Z—C02Q	118.0 (13)	C04F—C04D—C02A	127.0 (17)
C057—C020—C01I	120.8 (16)	C04F—C04D—C023	115.7 (16)
C057—C020—H020	119.6	C02A—C04D—C023	117.2 (15)
C01I—C020—H020	119.6	C042—C04E—C03V	122.6 (15)
C044—C021—H02B	109.5	C042—C04E—Cl07	119.0 (13)
C044—C021—H02C	109.5	C03V—C04E—Cl07	118.3 (13)
H02B—C021—H02C	109.5	C03A—C04F—C04D	124.0 (18)
C044—C021—H02D	109.5	C03A—C04F—H04F	118.0
H02B—C021—H02D	109.5	C04D—C04F—H04F	118.0
H02C—C021—H02D	109.5	C02I—C04G—H04A	109.5
N010—C022—C050	119.8 (14)	C02I—C04G—H04C	109.5
N010—C022—C01Y	120.7 (13)	H04A—C04G—H04C	109.5
C050—C022—C01Y	119.2 (15)	C02I—C04G—H04D	109.5
C03M—C023—C04O	121.4 (15)	H04A—C04G—H04D	109.5
C03M—C023—C04D	120.8 (14)	H04C—C04G—H04D	109.5
C04O—C023—C04D	117.8 (15)	C01P—C04H—C04W	124.0 (15)
C03Q—C024—C025	121.9 (13)	C01P—C04H—H04P	118.0
C03Q—C024—H024	119.0	C04W—C04H—H04P	118.0
C025—C024—H024	119.0	C02K—C04I—C03S	126 (2)
O00L—C025—C024	122.5 (14)	C02K—C04I—H04O	116.8
O00L—C025—C02O	116.6 (14)	C03S—C04I—H04O	116.8
C024—C025—C02O	120.9 (15)	N01K—C04J—C044	120.6 (13)
N01K—C026—C02I	119.9 (14)	N01K—C04J—C04M	117.1 (14)
N01K—C026—C05G	117.0 (14)	C044—C04J—C04M	122.2 (14)
C02I—C026—C05G	123.0 (15)	N018—C04K—C02G	116.8 (14)
O00O—C027—C01E	125.4 (13)	N018—C04K—C03L	121.0 (14)
O00O—C027—C058	115.9 (13)	C02G—C04K—C03L	122.2 (15)
C01E—C027—C058	118.7 (13)	N013—C04L—C03K	119.8 (14)
N019—C028—C035	118.7 (14)	N013—C04L—C04U	119.7 (14)
N019—C028—C01W	121.5 (14)	C03K—C04L—C04U	120.6 (15)
C035—C028—C01W	119.8 (14)	C04J—C04M—H04E	109.5
C05I—C029—C03Q	122.4 (16)	C04J—C04M—H04G	109.5
C05I—C029—Cl05	118.5 (13)	H04E—C04M—H04G	109.5
C03Q—C029—Cl05	119.0 (12)	C04J—C04M—H04H	109.5
C03H—C02A—C04D	124.5 (16)	H04E—C04M—H04H	109.5
C03H—C02A—H02A	117.7	H04G—C04M—H04H	109.5
C04D—C02A—H02A	117.7	C01O—C04N—C01Z	122.9 (13)
C01N—C02B—C02M	120.5 (13)	C01O—C04N—Cl04	119.6 (11)
C01N—C02B—H02J	119.8	C01Z—C04N—Cl04	117.5 (11)
C02M—C02B—H02J	119.8	C023—C04O—C05E	121.0 (16)
N017—C02C—C045	122.5 (13)	C023—C04O—C047	117.8 (14)
N017—C02C—C01P	118.4 (14)	C05E—C04O—C047	121.2 (15)
C045—C02C—C01P	119.1 (13)	C01Q—C04P—C01O	121.3 (15)
C03O—C02D—C01J	118.8 (15)	C01Q—C04P—Cl0B	121.6 (12)
C03O—C02D—H02H	120.6	C01O—C04P—Cl0B	116.7 (12)
C01J—C02D—H02H	120.6	C05M—C04Q—C2	117.2 (17)
N00Z—C02E—C02N	121.4 (15)	C05M—C04Q—H04Q	121.4
N00Z—C02E—C1	119.8 (13)	C2—C04Q—H04Q	121.4
C02N—C02E—C1	118.7 (14)	C03N—C04R—C01V	117.1 (14)
N016—C02F—C03G	118.3 (14)	C03N—C04R—Cl02	122.5 (12)
N016—C02F—C03C	117.8 (14)	C01V—C04R—Cl02	120.5 (13)
C03G—C02F—C03C	124.0 (15)	C04B—C04S—C03X	121.4 (17)
C04K—C02G—N00S	122.8 (13)	C04B—C04S—H04S	119.3
C04K—C02G—C04V	121.2 (14)	C03X—C04S—H04S	119.3
N00S—C02G—C04V	116.0 (13)	C01W—C04T—C05C	125.8 (19)
C03P—C02H—C01G	120.2 (16)	C01W—C04T—H04T	117.1
C03P—C02H—H02I	119.9	C05C—C04T—H04T	117.1
C01G—C02H—H02I	119.9	C04L—C04U—H04L	109.5
N00Q—C02I—C026	120.4 (14)	C04L—C04U—H04M	109.5
N00Q—C02I—C04G	116.6 (13)	H04L—C04U—H04M	109.5
C026—C02I—C04G	122.9 (14)	C04L—C04U—H04N	109.5
N010—C02J—C031	123.9 (14)	H04L—C04U—H04N	109.5
N010—C02J—C05M	116.0 (13)	H04M—C04U—H04N	109.5
C031—C02J—C05M	120.0 (14)	C02G—C04V—H04I	109.5
C04I—C02K—C01Y	115.1 (16)	C02G—C04V—H04J	109.5
C04I—C02K—H02K	122.4	H04I—C04V—H04J	109.5
C01Y—C02K—H02K	122.4	C02G—C04V—H04K	109.5
C01X—C02L—C01D	122.1 (14)	H04I—C04V—H04K	109.5
C01X—C02L—H02L	118.9	H04J—C04V—H04K	109.5
C01D—C02L—H02L	118.9	C04X—C04W—C04H	117.5 (14)
O00U—C02M—C02B	123.0 (13)	C04X—C04W—H04W	121.2
O00U—C02M—C05P	118.6 (14)	C04H—C04W—H04W	121.2
C02B—C02M—C05P	118.4 (13)	C04W—C04X—C045	122.6 (15)
N014—C02N—C02E	121.6 (13)	C04W—C04X—H04X	118.7
N014—C02N—C05K	119.5 (13)	C045—C04X—H04X	118.7
C02E—C02N—C05K	118.9 (14)	C04Z—C04Y—C058	120.7 (15)
C025—C02O—C05I	117.2 (14)	C04Z—C04Y—H04Y	119.6
C025—C02O—Cl0E	122.6 (12)	C058—C04Y—H04Y	119.6
C05I—C02O—Cl0E	120.2 (12)	C04Y—C04Z—C04A	122.6 (15)
O00X—C02P—C03W	120.4 (14)	C04Y—C04Z—Cl0C	118.8 (12)
O00X—C02P—C03T	120.5 (14)	C04A—C04Z—Cl0C	118.5 (13)
C03W—C02P—C03T	119.0 (15)	C022—C050—C03S	118.2 (15)
C01Q—C02Q—C01Z	118.0 (14)	C022—C050—H050	120.9
C01Q—C02Q—H02Q	121.0	C03S—C050—H050	120.9
C01Z—C02Q—H02Q	121.0	C05K—C051—C056	120.2 (17)
C041—C02R—C01H	117.5 (15)	C05K—C051—H051	119.9
C041—C02R—H02R	121.3	C056—C051—H051	119.9
C01H—C02R—H02R	121.3	C05N—C052—C040	117.4 (18)
C03I—C02S—C02U	120.0 (14)	C05N—C052—H052	121.3
C03I—C02S—C03U	122.3 (16)	C040—C052—H052	121.3
C02U—C02S—C03U	117.7 (15)	C01C—C053—H05F	109.5
C03U—C02T—C03X	124.1 (16)	C01C—C053—H05G	109.5
C03U—C02T—H02T	117.9	H05F—C053—H05G	109.5
C03X—C02T—H02T	117.9	C01C—C053—H05H	109.5
C02S—C02U—C03B	121.1 (14)	H05F—C053—H05H	109.5
C02S—C02U—C05F	118.2 (15)	H05G—C053—H05H	109.5
C03B—C02U—C05F	120.7 (15)	C03D—C054—H05I	109.5
C03G—C02V—H02E	109.5	C03D—C054—H05J	109.5
C03G—C02V—H02F	109.5	H05I—C054—H05J	109.5
H02E—C02V—H02F	109.5	C03D—C054—H05N	109.5
C03G—C02V—H02G	109.5	H05I—C054—H05N	109.5
H02E—C02V—H02G	109.5	H05J—C054—H05N	109.5
H02F—C02V—H02G	109.5	C05D—C055—C046	120.3 (16)
C03N—C02W—C048	120.0 (14)	C05D—C055—C03B	121.2 (16)
C03N—C02W—Cl0D	120.1 (11)	C046—C055—C03B	118.4 (15)
C048—C02W—Cl0D	119.8 (12)	C1—C056—C051	121.4 (16)
C05C—C02X—C035	118.8 (17)	C1—C056—H056	119.3
C05C—C02X—H02X	120.6	C051—C056—H056	119.3
C035—C02X—H02X	120.6	C020—C057—C041	117.6 (16)
C01U—C02Y—C01X	118.3 (14)	C020—C057—H057	121.2
C01U—C02Y—Cl09	121.4 (11)	C041—C057—H057	121.2
C01X—C02Y—Cl09	120.3 (13)	C04Y—C058—C027	117.2 (15)
C01U—C02Z—C01D	120.8 (15)	C04Y—C058—Cl01	122.6 (12)
C01U—C02Z—Cl0F	118.9 (11)	C027—C058—Cl01	120.2 (12)
C01D—C02Z—Cl0F	120.2 (13)	C046—C059—C05F	123.9 (16)
N018—C030—C01S	121.7 (14)	C046—C059—H059	118.1
N018—C030—C036	116.8 (14)	C05F—C059—H059	118.1
C01S—C030—C036	121.5 (15)	N015—C05A—C03D	120.6 (14)
N00W—C031—C033	121.7 (15)	N015—C05A—C05H	115.5 (13)
N00W—C031—C02J	119.6 (14)	C03D—C05A—C05H	123.8 (14)
C033—C031—C02J	118.7 (15)	C049—C05B—C047	121.8 (17)
C03I—C032—C043	119.7 (17)	C049—C05B—H05B	119.1
C03I—C032—H032	120.1	C047—C05B—H05B	119.1
C043—C032—H032	120.1	C02X—C05C—C04T	116.6 (18)
C2—C033—C031	124.4 (17)	C02X—C05C—H05S	121.7
C2—C033—H033	117.8	C04T—C05C—H05S	121.7
C031—C033—H033	117.8	C055—C05D—C04B	118.6 (17)
C01A—C034—C01F	119.0 (15)	C055—C05D—H05D	120.7
C01A—C034—Cl03	119.0 (12)	C04B—C05D—H05D	120.7
C01F—C034—Cl03	122.0 (12)	C05Q—C05E—C04O	120.5 (16)
N01T—C035—C028	123.4 (14)	C05Q—C05E—C03H	121.2 (16)
N01T—C035—C02X	116.3 (15)	C04O—C05E—C03H	118.2 (16)
C028—C035—C02X	120.1 (15)	C043—C05F—C059	124.8 (16)
C030—C036—H03B	109.5	C043—C05F—C02U	118.3 (16)
C030—C036—H03C	109.5	C059—C05F—C02U	116.8 (17)
H03B—C036—H03C	109.5	C026—C05G—H05A	109.5
C030—C036—H03D	109.5	C026—C05G—H05C	109.5
H03B—C036—H03D	109.5	H05A—C05G—H05C	109.5
H03C—C036—H03D	109.5	C026—C05G—H05E	109.5
C03A—C037—C03M	121.1 (15)	H05A—C05G—H05E	109.5
C03A—C037—H037	119.5	H05C—C05G—H05E	109.5
C03M—C037—H037	119.5	C05A—C05H—H05O	109.5
C01B—C038—H03M	109.5	C05A—C05H—H05P	109.5
C01B—C038—H03N	109.5	H05O—C05H—H05P	109.5
H03M—C038—H03N	109.5	C05A—C05H—H05R	109.5
C01B—C038—H03O	109.5	H05O—C05H—H05R	109.5
H03M—C038—H03O	109.5	H05P—C05H—H05R	109.5
H03N—C038—H03O	109.5	C029—C05I—C02O	119.1 (15)
C03K—C039—H03P	109.5	C029—C05I—H05V	120.4
C03K—C039—H03Q	109.5	C02O—C05I—H05V	120.4
H03P—C039—H03Q	109.5	C042—C05J—C03Y	122.8 (14)
C03K—C039—H03R	109.5	C042—C05J—Cl0G	118.7 (12)
H03P—C039—H03R	109.5	C03Y—C05J—Cl0G	118.4 (14)
H03Q—C039—H03R	109.5	C051—C05K—C02N	120.9 (16)
C037—C03A—C04F	120.4 (16)	C051—C05K—H05K	119.6
C037—C03A—H03A	119.8	C02N—C05K—H05K	119.6
C04F—C03A—H03A	119.8	C03Z—C05L—C047	121.4 (16)
C03X—C03B—C02U	120.8 (15)	C03Z—C05L—H05L	119.3
C03X—C03B—C055	119.3 (15)	C047—C05L—H05L	119.3
C02U—C03B—C055	119.8 (14)	C04Q—C05M—C02J	120.5 (16)
C02F—C03C—H03T	109.5	C04Q—C05M—H05M	119.7
C02F—C03C—H03V	109.5	C02J—C05M—H05M	119.7
H03T—C03C—H03V	109.5	C05O—C05N—C052	127.6 (18)
C02F—C03C—H03W	109.5	C05O—C05N—H05T	116.2
H03T—C03C—H03W	109.5	C052—C05N—H05T	116.2
H03V—C03C—H03W	109.5	C05N—C05O—C04C	115.8 (17)
N016—C03D—C05A	120.8 (14)	C05N—C05O—H05U	122.1
N016—C03D—C054	120.0 (14)	C04C—C05O—H05U	122.1
C05A—C03D—C054	119.2 (15)	C03R—C05P—C02M	120.6 (15)
N019—C03E—C040	118.0 (14)	C03R—C05P—Cl08	119.8 (12)
N019—C03E—C04C	122.2 (13)	C02M—C05P—Cl08	119.4 (12)
C040—C03E—C04C	119.8 (14)	C05E—C05Q—C03Z	118.1 (17)
C01S—C03F—H03E	109.5	C05E—C05Q—H05Q	120.9
C01S—C03F—H03F	109.5	C03Z—C05Q—H05Q	120.9
H03E—C03F—H03F	109.5	C056—C1—C02E	119.9 (15)
C01S—C03F—H03G	109.5	C056—C1—H1	120.1
H03E—C03F—H03G	109.5	C02E—C1—H1	120.1
H03F—C03F—H03G	109.5	C033—C2—C04Q	119.1 (17)
N015—C03G—C02F	122.7 (14)	C033—C2—H2	120.4
N015—C03G—C02V	117.2 (15)	C04Q—C2—H2	120.4