Four- and five-component molecular solids: crystal engineering strategies based on structural inequivalence

A synthetic strategy is described for the co-crystallization of four- and five-component molecular crystals, based on the fact that if any particular chemical constituent of a lower cocrystal is found in two different structural environments, these differences may be exploited to increase the number of components in the solid. 2-Methylresorcinol and tetramethylpyrazine are basic template molecules that allow for further supramolecular homologation. Ten stoichiometric quaternary cocrystals and one quintinary cocrystal with some solid solution character are reported. Cocrystals that do not lend themselves to such homologation are termed synthetic dead ends.

1. Introduction

Retrosynthetic analysis with supramolecular synthons remains at the cornerstone of logic driven crystal engineering (Desiraju, 1995). Supramolecular synthons encapsulate critical shape and chemical recognition information and are the structural units that persist through all stages of crystallization (Desiraju, 1997a; Desiraju, 2007). Crystal engineering is a form of solid state supramolecular synthesis (Desiraju, 1997b) and the complexity of a synthetic target is assessed in terms of precise orientations and topologies of specified chemical constituents, and the eventual aim is a crystal architecture with pre-desired properties (Desiraju et al., 2011). Crystallization, since antiquity, has been a method of purification and it is an excluding rather than an including phenomenon. Generally speaking, when a mixture of compounds is taken for crystallization, the outcome is a single component crystal. Multi-component crystals are more difficult to obtain, and their isolation is often unpredictable. The formation of a two-component crystal AB from A and B implies that interactions of the type A⋯B are better in some respect than interactions of the type A⋯A or B⋯B, with the caveat that these interactions involve either or both shape and chemical recognition. Therefore, obtaining a multi-component crystal means that one is able to calibrate and assess intermolecular interactions rather carefully. These multi-component crystals (Bond, 2007), also called cocrystals, have been known since the isolation of quinhydrone (Wöhler, 1844). Binary cocrystals are of importance in the pharmaceutical industry (Almarsson & Zaworotko, 2004; Wouters & Quéré, 2012; Stahly, 2009). Making a binary cocrystal is now well within the scope of crystal engineering (Desiraju et al., 2011).

Increasing the number of components in a cocrystal is a crystal engineering equivalent of synthetic complexity (Aakeröy et al., 2001, 2005). This is because when one cocrystallizes compounds such as A, B and C, one may well obtain binary cocrystals AB, BC, AC rather than the desired ternary ABC. Design strategies for ternary cocrystals are based on exploiting chemical differences in the selected molecules (Bučar et al., 2012; Seaton et al., 2013; Chakraborty et al., 2014; Dobrowolski et al., 2014; Bolla & Nangia, 2015). Ditopic hydrogen bond donors and acceptors may be manipulated so that a hierarchy of hydrogen bonds emerge, facilitating the formation of ternary cocrystals (Dubey & Desiraju, 2014, 2015; Mir et al., 2015). Alternatively, interactions of different strengths or types may be employed so that a hierarchy is established (Chakraborty et al., 2014; Tothadi & Desiraju, 2013). Strong hydrogen bonds, weak hydrogen bonds, halogen bonds, π⋯π interactions and van der Waals interactions may be used in a modular and pre-determined manner to give an interaction orthogonality that is sufficient to form ternary cocrystals. Typically, in an assembly of the type A⋯B⋯C, the interactions B⋯C could be weaker than the interaction A⋯B while an interaction of the type A⋯C may be so feeble that it need not be considered (Bolla & Nangia, 2015). If B⋯C is sufficiently close in effectiveness to A⋯B then ternary A⋯B⋯C would be preferred to binaries A⋯B and B⋯C. This strategy is surprisingly effective and we (Chakraborty et al., 2014; Dubey & Desiraju, 2014, 2015; Mir et al., 2015; Tothadi & Desiraju, 2013) and others (Aakeröy et al., 2001, 2005; Seaton et al., 2013) have reported cases where ternaries are obtained exclusively in the absence of binaries. Certain techniques of `supramolecular homologation' may also be used, for example, a diacid may be inserted into an amide⋯amide homosynthon without interfering with other interactions in the system (Tothadi & Desiraju, 2013). This would reliably increase the number of components in a system by one. Shape and chemical arguments may be used together and provide greater control (Bhogala et al., 2005; Moorthy et al., 2010; Tothadi et al., 2011). Host–guest compounds with cavities of different sizes could accommodate guests of specific sizes.

One may ask whether stoichiometric four- and five-component cocrystals can even be prepared given the large number of crystallization possibilities that would seem to be available. In this study, a four-component crystal is taken as one in which four solid components are crystallized together to obtain a single crystalline product that contains all four compounds in a stoichiometric ratio. Such a definition excludes, for example, solvates/hydrates in which the solvent is the third and/or the fourth component and in which introduction of the solvent was not deliberately engineered or even anticipated (this is mostly true of water which need not even be taken as a crystallizing solvent but can still appear in the final crystal) (Clarke et al., 2012), and also solid solution type entities which are obtained by statistical crystallization techniques (Bhogala & Nangia, 2008). With such a definition, cocrystallization of a mixture of four compounds could, in principle, give not only binaries but also a number of ternaries. In the end, it would appear that the level and degree of control to make a quaternary cocrystal is formidable.

2. Experimental

Single-crystal X-ray data for all the crystals were collected on a Rigaku Mercury 375/M CCD (XtaLAB mini) diffractometer using graphite monochromator Mo Kα radiation at 150 K and were processed with CrystalClear software (Rigaku, 2009). Some datasets were collected on a Bruker D8 Quest diffractometer equipped with an Oxford cryosystems N₂ open-flow cryostat using Mo Kα radiation. Data integration and data reduction were carried out with the SAINT-Plus program (Bruker, 2006). Structure solution and refinement were performed using SHELX2013 (Sheldrick, 2015) embedded in the WinGX suite (Farrugia, 1999). All non-H atoms were refined anisotropically by the full-matrix least-squares method. H atoms were fixed on the riding model and some of the acidic H atoms were located via Fourier maps. Mercury Version 3.5 (Macrae et al., 2008) was used for molecular representations and packing diagrams.

For crystallization, liquid assisted or solvent assisted grinding procedures were employed. In this method the solid components to be crystallized are taken together in definite stoichiometric ratios in a mortar along with few drops of a solvent. The mixture is then ground with a pestle and the process is repeated 2–3 times to get a homogenous mixture. The solid mixture is then taken for crystallizations in different solvents. Detailed crystallization descriptions have been provided in the supporting information .

3. Results and discussion

This letter describes a concise synthetic strategy to increase the number of components in a crystal from one to two (Mir et al., 2015), to three, to four and eventually to five. The strategy is outlined schematically in Fig. 1 and in cartoon fashion in Fig. 2. In Fig. 1 and henceforth in this paper the letters A, B, C, D and E refer to molecules in certain crystal environments rather than to the compounds themselves. The strategy is based on the fact that if any particular component in a cocrystal is found in two different environments, these differences may be exploited to increase the number of components. Molecules A and B are chosen so that two types of binaries are obtained. In the first, the same chemical functionalities in A or B are located in the same crystal environment and are not susceptible to any further supramolecular differentiation. In the second type, however, the same functional groups in say B are found in two types of crystal environments which we shall refer to as B₁ and B₂, or they are potentially capable of such differentiation (Smolka et al., 1999). These crystal environments (or potential environments) may be sufficiently distinct so that a new entity C that is introduced will be able to discriminate between the sites and replace just one of B₁ or B₂, to give a ternary. These ternaries may be of two types: in the first, the three components A, B and C are found in a single crystallographic environment each and in the second, one of the components, say C is found in two slightly different crystallographic environments. We shall refer to these as ABC and ABC₁C₂, respectively. So, in the next step, if a fourth component D is taken for the crystallization experiment there is a possibility of obtaining a quaternary ABCD. Finally, the same strategy may be employed in the favorable case where ABCD₁D₂ is obtained, to arrive at a quintinary cocrystal ABCDE. This design strategy is illustrated in this research letter with the prototype 2-methylresorcinol (MRE).

Figure 1 Schematic representation for the synthesis of multi-component crystals. Here, A, B, C, D and E refer to the molecule in distinct crystal environments. B1, B2 refer to the breakdown of structural equivalence at site B, and similarly for sites C and D.

Figure 2 Cartoon representation of crystal synthesis for multi-component crystals. Here, color coding and shapes represent distinct chemical and geometrical features of the molecules.

We have reported binary and ternary cocrystals of MRE (Mir et al., 2015). Here (Fig. 3) we have selected tetramethylpyrazine (TMP) as a coformer that provides an O—H⋯N mediated 1:1 MRE:TMP cocrystal of the type AB₁B₂ (the two O—H⋯N metrics are different, for example). This lack of structural equivalence has been previously utilized in the synthesis of hydrogen-bonded ternary solids ABC, for instance in the 2:1:2 solid MRE·TMP·4DMAP (4DMAP is 4-dimethylaminopyridine). Here, we preferred to modulate interaction strength and selected flat aromatic molecules (PAH) that can form weak C—H⋯π interactions with the methyl groups of TMP. For example, an equimolar ratio of pyrene (PYR) as a template with MRE and TMP provides a stoichiometric 1:1:1 MRE:TMP:PYR ternary solid in which each molecule occupies its own distinct crystal environment. We extended the generality of this strategy with anthracene (ANT) and hexamethylbenzene (HMB) and isolated 1:1:1 MRE:TMP:ANT and 1:1:1 MRE:TMP:HMB ternary solids, respectively (Fig. 4). These crystal structures follow from a situation wherein O—H⋯N hydrogen-bond inequivalences in the binary MRE:TMP cocrystal are exploited to achieve incorporation of the third component. As mentioned by us previously, the ternaries thus obtained were largely uncontaminated by binaries (as monitored with powder X-ray diffraction).

Figure 3 Synthetic scheme for multicomponent crystals. A, B, C, D and E are representative molecules. Note the systematic insertion of components in each step using structural differentiations available in the crystal.

Figure 4 Quaternary cocrystal. The MRE:TMP:PYR ternary solid (top) is a synthetic dead end. The MRE:TMP:22TP:DPE-I quaternary solid may be considered as a development of the MRE:TMP:22TP ternary (bottom) in which the one of the MREs is replaced by the fourth component DPE-I using O—H⋯N hydrogen bonding.

However, this is not the only type of ternary cocrystal that is obtained. Figs. 2 and 4 show two other types: biphenyl (BP), 2,2′-bipyridine (22BP) and 2,2′-bisthiophene (22TP) yield 1:1:1 solids with MRE and TMP with O—H⋯O hydrogen bonds between MRE molecules; acridine (ACR), perylene (PER), phenazine (PHE) and tolan (TOL) give ternaries wherein the ditopic MRE and TMP form an infinite O—H⋯N pattern. However, only every alternate molecule of TMP is involved in C—H⋯π stacking with the third component. An important difference between these two types of ternary and the PYR type is that the PYR type does not lend itself to upgradation into a quaternary (Fig. 4). There is no inequivalence at any of the three sites A, B or C. It is a synthetic dead end. In the ACR and 22TP types, however, there is a differentiation of structural sites: in the ACR group only one of the TMP molecules is stacked with the PAH; in the 22TP type, MRE forms O—H⋯N and O—H⋯O hydrogen bonds at different sites. Accordingly, these inequivalences may be likened to C₁ and C₂ in the scheme shown in Fig. 1. So, we could replace the (unstacked) TMP in the ACR group with another ditopic acceptor such as 1,2-bis(4-pyridyl)ethylene (DPE-I). Using the 22TP ternary as a conceptual starting point for a quaternary, we are effectively replacing an O—H⋯O hydrogen bond with an O—H⋯N by using DPE-I or DPE-II. We obtained six four-component cocrystals ABCD with DPE-I or the nearly similar 1,2-bis(4-pyridyl)ethane (DPE-II) as the fourth component and each of BP, 22BP and 22TP as the third component. Typical examples are the 2:1:1:1 solids MRE:TMP:22TP:DPE-I and 2:1:1:1 MRE:TMP:BP:DPE-II, which is ABCD in Fig. 1. This is the first report in which four solids are taken together for crystallization and the product is a single phase that contains all four chemical species in a fixed stoichiometry.

Four more quaternaries were obtained in which the crystal structures arise from the ACR group of ternaries. These solids are derived from the 1:2:1 MRE:TMP:ACR structure in which all or half of the unstacked TMP molecules are replaced by DPE-I or DPE-II. Accordingly, one may understand the crystal structures of 3:2:2:1 MRE:TMP:ACR:DPE-I and MRE:TMP:ACR:DPE-II. In the 4:3:2:1 MRE:TMP:ACR:DPE-I cocrystal, only half the unstacked TMP molecules are replaced by DPE and the structure is of mechanistic relevance in the crystallization of the 3:2:2:1 solids (see S2 for details). The last quaternary is 3:2:2:1 MRE:TMP:ANT:DPE-II and it was obtained not through retrosynthesis but rather through a high throughput procedure. In this context, ANT occurs in a dead end ternary. In three of these four quaternaries (MRE:TMP:ACR:DPE-I, MRE:TMP:ACR:DPE-II, MRE:TMP:ANT:DPE-II) MRE molecules occur in ordered and disordered environments. When ordered, MRE forms O—H⋯N hydrogen bonds with DPE and TMP. When disordered, it lies on an inversion center and forms O—H⋯N hydrogen bonds with only TMP. These MRE sites represent a further inequivalence and the solid may be likened to ABCD₁D₂ in Fig. 1. To summarize, the 10 quaternaries we have reported here may be divided into three groups: six of them are 2:1:1:1 ABCD solids and are synthetic dead ends; one is a 4:3:2:1 outlier; the other three are of the ABCD₁D₂ type and could lend themselves to further development into a quintinary cocrystal.

The synthetic strategy towards a five-component crystal uses the fact that the disordered MRE molecule in the ACR quaternaries (Fig. 2) is chemically and geometrically equivalent to a molecule of 1,2,4,5-tetrahydroxy-3,6-dimethylbenzene, and may therefore be replaced by it as a solid solution. This strategy has been used to make a ternary cocrystal from a binary (Bučar et al., 2012). The tetrahydroxy molecule is, however, too unstable to isolate. A surrogate molecule, trimethylhydroquinone (TMHQ), based on OH/CH₃ exchange, was identified. It was expected that TMHQ would replace the disordered MRE but not the ordered MRE. A mixture of ACR, DPE-II, MRE, TMHQ and TMP were taken together for crystallization in MeNO₂, with the first four compounds in equimolar ratio and TMHQ in fivefold excess of the desired 100% occupancy in the disordered MRE site D₂. A single solid was obtained in the form of yellow brown blocks; the quaternary is pale yellow to colorless (S3 ). A single crystal was selected and the cell parameters found to be identical to the quaternary. The same crystal was dissolved in MeOH and the GC–MS spectra traces recorded. The GC trace shows the clear presence of five components (S3 ). The crystal is therefore a five-component crystal. The MS identifies four of the compounds as MRE (m/z = 124), TMP (m/z = 136), DPE-II (m/z = 184) and ACR (m/z = 179), but the fifth compound is not TMHQ but rather its oxidation product 2,3,5-trimethyl-1,4-benzoquinone (TMBQ) with its characteristic molecular ion peak at m/z = 150. We thus identify (Fig. 5) the five-component solid (MRE)_3 − x·TMP₂·ACR₂·DPE-II·TMBQ_x in which the fifth component, TMBQ, is not present in a stoichiometric amount.

Figure 5 Retrosynthesis of quintinary solids. The MRE:TMP:ACR:DPE-II quaternary solid (top) has a disordered MRE that is replaced by the topologically similar TMBQ molecule in the crystal.

Least-squares refinement of the X-ray data of the quintinary cocrystal shows the presence of TMBQ but the TMBQ:MRE ratio in the disordered inversion site cannot be estimated (S3 ). Considering that TMHQ is very prone to oxidation, and the crystal of the suspected quintinary is brown–yellow, it is concluded that TMHQ gets oxidized to TMBQ in solution and the latter enters the crystal in the disordered MRE site. TMBQ has the required topological similarities to occupy this site and has the shape–size mimicry with MRE that was anticipated for TMHQ. While TMBQ is bound in the site with C—H⋯N hydrogen bonds (S3 ), these are weaker than the O—H⋯N bonds formed by MRE. TMBQ cannot compete so well with the MRE for hydrogen bonding to TMP, but it still enters the crystal to some small extent (we estimate 5%) justifying the design strategy of using the lack of equivalence of the D site in the quaternary cocrystal to introduce the fifth component. There is a precedent for this kind of solid solution behavior in the system barbital–urea–acetamide (Thakur et al., 2010). It is emphasized that the five-component solid obtained here is not, strictly speaking, a quintinary cocrystal, if by the latter term is meant a solid in which five different solid compounds are present in stoichiometric amounts. However, the present strategy outlines an approach to such cocrystals.

4. Conclusions

Four- and higher-component molecular crystals can be designed with crystal engineering principles. In the 10 quaternary and one quintinary cocrystal reported here, the components are introduced into the solid using logic driven protocols and they occur in stoichiometric ratios, except for the fifth component TMBQ in the quintinary which enters the cocrystal in a solid solution manner. All the new solids we report contain the crucial components 2-methylresorcinol (MRE) and tetramethylpyrazine (TMP). In all cases there is an O—H⋯N hydrogen bond between these entities. Success rates in the crystallizations are quite high (around 75% and the unsuccessful 25% cases are mostly ones where a selected PAH molecule failed to give the desired product, see S4 ) and one may well ask why this is the case.

Some points need further discussion. The modularity of the entire sequence would seem to hint that synthons present in the crystals are also present in the crystallizing solution. Once the binary to ternary progression was made, it was possible to think of the ternary to quaternary progression in the same terms: the key elements of the ternary structures are likely to be present in solution, and the fourth component is seemingly `added' to give the quaternary. One of the reasons for the success rate of this strategy could be that none of the components contain very good hydrogen bond donor or acceptor groups. The strongest hydrogen bond in the system is the O—H<sub>phenol</sub>⋯N<sub>pyridine</sub> interaction. There are no acids, amides and other similar compounds in any of these new cocrystals. Good donors and acceptors lead necessarily to strong hydrogen bonds and these lead to stable lower component cocrystals (binary, ternary) that act as synthetic terminators or dead ends. The essence of making a quaternary (or higher) cocrystal seems to be a selection of molecules, all of which associate with comparable intermolecular interactions. Perhaps it is also this feature that allows for the breakdown of structural equivalence (B → B<sub>1</sub>, B<sub>2</sub>; C → C<sub>1</sub>, C<sub>2</sub>; D → D<sub>1</sub>, D<sub>2</sub>) throughout the reaction cascade, and which has been used to make ternaries from binaries, quaternaries from ternaries and so on. Also of interest is the idea of sites that are `potentially' inequivalent. In the MRE:TMP binary in Fig. 2, all TMP molecules are identical. However, C—H⋯π stacking with a PAH causes an inequivalence (C → C₁, C₂) in cases where the PAH is larger or more polar (ACR, PER, PHE, TOL) and where perhaps stacking at the second site is hindered because of stereoelectronic factors. Smaller and/or less polar PAH molecules (ANT, HMB, PYR) stack at both sites leading to dead end ternaries.

Crystallization proceeds from solution and this modularity is very strong evidence for the persistence of small and large supramolecular synthons in solution (Mukherjee et al., 2014). The nucleation of a higher component crystal may be visualized as occurring via the attachment of the nth component to an (n − 1) cluster in solution. This is the crux of synthon theory (Desiraju, 1995). The design of each new crystal is not an ab initio exercise (Dunitz, 2015; Thakur et al., 2015; Lecomte et al., 2015). Smaller and larger synthons and clusters are sufficiently stable kinetically so that crystal build-up can be analyzed retrosynthetically.

Supporting information

Computing details

For all compounds, program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013).

(MRE_TMP_22BP)

Crystal data

C32H36N4O4	Z = 2
Mr = 540.65	F(000) = 576
Monoclinic, P21/n	Dx = 1.277 Mg m^−3
a = 7.8566 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 21.336 (4) Å	µ = 0.09 mm^−1
c = 8.3872 (17) Å	T = 150 K
β = 90.911 (11)°	Block, colorless
V = 1405.8 (5) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2925 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.092
profile data from ω–scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −10→10
Tmin = 0.983, Tmax = 0.983	k = −27→27
14373 measured reflections	l = −10→10
3224 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) = 0.174	w = 1/[σ^2(Fo^2) + (0.094P)^2 + 0.5103P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
3224 reflections	Δρmax = 0.51 e Å^−3
186 parameters	Δρmin = −0.31 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.61159 (14)	0.14356 (5)	0.18886 (13)	0.0257 (3)
H1	0.5823	0.1160	0.2544	0.039*
O2	0.37775 (15)	0.29025 (6)	−0.17446 (14)	0.0302 (3)
H2	0.2842	0.3047	−0.2074	0.045*
N1	0.54103 (16)	0.04834 (6)	0.39891 (15)	0.0220 (3)
C1	0.49383 (19)	0.21591 (6)	0.00284 (17)	0.0216 (3)
C2	0.46884 (19)	0.16724 (7)	0.11193 (17)	0.0211 (3)
C5	0.1865 (2)	0.21810 (8)	−0.04573 (19)	0.0273 (3)
H5	0.0902	0.2353	−0.1001	0.033*
C6	0.3492 (2)	0.24141 (7)	−0.07289 (18)	0.0233 (3)
C9	0.47762 (19)	0.06073 (7)	0.54315 (18)	0.0219 (3)
C3	0.3070 (2)	0.14372 (7)	0.14232 (18)	0.0250 (3)
H3	0.2924	0.1107	0.2168	0.030*
C10	0.56394 (19)	−0.01141 (7)	0.35443 (17)	0.0213 (3)
C7	0.6681 (2)	0.24118 (8)	−0.0327 (2)	0.0327 (4)
H7A	0.6908	0.2782	0.0336	0.049*
H7B	0.6732	0.2529	−0.1455	0.049*
H7C	0.7538	0.2090	−0.0093	0.049*
C4	0.1675 (2)	0.16932 (8)	0.0622 (2)	0.0288 (4)
H4	0.0571	0.1532	0.0815	0.035*
C8	0.4524 (2)	0.12797 (8)	0.5889 (2)	0.0323 (4)
H8A	0.4793	0.1550	0.4983	0.049*
H8B	0.5277	0.1383	0.6794	0.049*
H8C	0.3338	0.1346	0.6190	0.049*
C11	0.6353 (2)	−0.02326 (9)	0.19232 (18)	0.0308 (4)
H11A	0.6614	0.0168	0.1412	0.046*
H11B	0.5515	−0.0461	0.1270	0.046*
H11C	0.7396	−0.0482	0.2029	0.046*
N2	0.0836 (2)	0.01554 (7)	0.30583 (18)	0.0336 (4)
C16	0.0326 (2)	−0.01815 (8)	0.43041 (19)	0.0269 (4)
C15	0.0396 (2)	−0.08328 (9)	0.4346 (2)	0.0316 (4)
H15	0.0039	−0.1056	0.5261	0.038*
C14	0.0998 (2)	−0.11499 (9)	0.3024 (2)	0.0372 (4)
H14	0.1050	−0.1595	0.3014	0.045*
C12	0.1411 (3)	−0.01595 (9)	0.1802 (2)	0.0372 (4)
H12	0.1768	0.0075	0.0905	0.045*
C13	0.1520 (2)	−0.08058 (10)	0.1721 (2)	0.0385 (4)
H13	0.1942	−0.1008	0.0798	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0291 (6)	0.0220 (5)	0.0259 (6)	−0.0042 (4)	−0.0023 (4)	0.0078 (4)
O2	0.0327 (6)	0.0260 (6)	0.0319 (6)	0.0008 (4)	−0.0030 (5)	0.0092 (5)
N1	0.0265 (6)	0.0216 (6)	0.0179 (6)	0.0000 (5)	0.0001 (5)	0.0023 (5)
C1	0.0274 (7)	0.0168 (7)	0.0207 (7)	−0.0021 (5)	0.0012 (5)	−0.0010 (5)
C2	0.0272 (7)	0.0180 (7)	0.0182 (6)	−0.0017 (5)	0.0008 (5)	−0.0029 (5)
C5	0.0261 (7)	0.0280 (8)	0.0279 (8)	0.0036 (6)	−0.0001 (6)	−0.0026 (6)
C6	0.0311 (8)	0.0180 (7)	0.0207 (7)	0.0004 (5)	0.0007 (5)	−0.0014 (5)
C9	0.0260 (7)	0.0201 (7)	0.0195 (7)	0.0012 (5)	−0.0015 (5)	0.0007 (5)
C3	0.0303 (8)	0.0231 (7)	0.0217 (7)	−0.0039 (6)	0.0048 (6)	−0.0008 (6)
C10	0.0248 (7)	0.0229 (7)	0.0161 (6)	0.0011 (5)	−0.0007 (5)	0.0004 (5)
C7	0.0289 (8)	0.0273 (8)	0.0417 (10)	−0.0062 (6)	−0.0005 (7)	0.0108 (7)
C4	0.0256 (7)	0.0314 (8)	0.0296 (8)	−0.0043 (6)	0.0061 (6)	−0.0037 (6)
C8	0.0443 (9)	0.0207 (8)	0.0320 (8)	0.0037 (7)	0.0016 (7)	−0.0020 (6)
C11	0.0411 (9)	0.0335 (9)	0.0179 (7)	0.0037 (7)	0.0059 (6)	0.0002 (6)
N2	0.0408 (8)	0.0332 (8)	0.0269 (7)	−0.0044 (6)	0.0060 (6)	−0.0001 (6)
C16	0.0263 (7)	0.0292 (8)	0.0252 (8)	−0.0044 (6)	−0.0014 (6)	−0.0004 (6)
C15	0.0347 (8)	0.0333 (9)	0.0268 (8)	−0.0030 (7)	0.0012 (6)	0.0027 (6)
C14	0.0438 (10)	0.0290 (9)	0.0390 (10)	−0.0026 (7)	0.0024 (8)	−0.0055 (7)
C12	0.0458 (10)	0.0387 (10)	0.0275 (9)	−0.0065 (8)	0.0079 (7)	−0.0015 (7)
C13	0.0405 (9)	0.0435 (11)	0.0317 (9)	−0.0052 (8)	0.0061 (7)	−0.0117 (8)

Geometric parameters (Å, º)

O1—C2	1.3807 (18)	C7—H7B	0.9800
O1—H1	0.8400	C7—H7C	0.9800
O2—C6	1.3667 (18)	C4—H4	0.9500
O2—H2	0.8400	C8—H8A	0.9800
N1—C10	1.3414 (19)	C8—H8B	0.9800
N1—C9	1.3420 (19)	C8—H8C	0.9800
C1—C2	1.400 (2)	C11—H11A	0.9800
C1—C6	1.403 (2)	C11—H11B	0.9800
C1—C7	1.506 (2)	C11—H11C	0.9800
C2—C3	1.394 (2)	N2—C12	1.335 (2)
C5—C4	1.389 (2)	N2—C16	1.335 (2)
C5—C6	1.394 (2)	C16—C15	1.391 (2)
C5—H5	0.9500	C16—C16^ii	1.498 (3)
C9—C10^i	1.400 (2)	C15—C14	1.388 (2)
C9—C8	1.499 (2)	C15—H15	0.9500
C3—C4	1.389 (2)	C14—C13	1.384 (3)
C3—H3	0.9500	C14—H14	0.9500
C10—C9^i	1.400 (2)	C12—C13	1.383 (3)
C10—C11	1.500 (2)	C12—H12	0.9500
C7—H7A	0.9800	C13—H13	0.9500
C2—O1—H1	109.5	C3—C4—H4	119.4
C6—O2—H2	109.5	C5—C4—H4	119.4
C10—N1—C9	119.42 (13)	C9—C8—H8A	109.5
C2—C1—C6	117.56 (13)	C9—C8—H8B	109.5
C2—C1—C7	122.17 (14)	H8A—C8—H8B	109.5
C6—C1—C7	120.27 (13)	C9—C8—H8C	109.5
O1—C2—C3	121.28 (13)	H8A—C8—H8C	109.5
O1—C2—C1	117.09 (13)	H8B—C8—H8C	109.5
C3—C2—C1	121.62 (14)	C10—C11—H11A	109.5
C4—C5—C6	118.81 (15)	C10—C11—H11B	109.5
C4—C5—H5	120.6	H11A—C11—H11B	109.5
C6—C5—H5	120.6	C10—C11—H11C	109.5
O2—C6—C5	122.27 (14)	H11A—C11—H11C	109.5
O2—C6—C1	115.99 (13)	H11B—C11—H11C	109.5
C5—C6—C1	121.74 (14)	C12—N2—C16	117.14 (16)
N1—C9—C10^i	119.91 (14)	N2—C16—C15	123.06 (15)
N1—C9—C8	118.15 (14)	N2—C16—C16^ii	116.23 (19)
C10^i—C9—C8	121.94 (14)	C15—C16—C16^ii	120.71 (18)
C4—C3—C2	119.01 (14)	C14—C15—C16	118.73 (16)
C4—C3—H3	120.5	C14—C15—H15	120.6
C2—C3—H3	120.5	C16—C15—H15	120.6
N1—C10—C9^i	120.67 (13)	C13—C14—C15	118.75 (18)
N1—C10—C11	117.77 (14)	C13—C14—H14	120.6
C9^i—C10—C11	121.57 (14)	C15—C14—H14	120.6
C1—C7—H7A	109.5	N2—C12—C13	124.25 (17)
C1—C7—H7B	109.5	N2—C12—H12	117.9
H7A—C7—H7B	109.5	C13—C12—H12	117.9
C1—C7—H7C	109.5	C12—C13—C14	118.06 (16)
H7A—C7—H7C	109.5	C12—C13—H13	121.0
H7B—C7—H7C	109.5	C14—C13—H13	121.0
C3—C4—C5	121.23 (14)
C6—C1—C2—O1	−178.37 (12)	C1—C2—C3—C4	0.0 (2)
C7—C1—C2—O1	1.1 (2)	C9—N1—C10—C9^i	0.0 (2)
C6—C1—C2—C3	1.4 (2)	C9—N1—C10—C11	−179.93 (14)
C7—C1—C2—C3	−179.18 (14)	C2—C3—C4—C5	−0.7 (2)
C4—C5—C6—O2	−178.48 (14)	C6—C5—C4—C3	−0.1 (2)
C4—C5—C6—C1	1.6 (2)	C12—N2—C16—C15	1.0 (2)
C2—C1—C6—O2	177.84 (13)	C12—N2—C16—C16^ii	−179.56 (18)
C7—C1—C6—O2	−1.6 (2)	N2—C16—C15—C14	−1.0 (3)
C2—C1—C6—C5	−2.2 (2)	C16^ii—C16—C15—C14	179.52 (18)
C7—C1—C6—C5	178.37 (14)	C16—C15—C14—C13	0.6 (3)
C10—N1—C9—C10^i	0.0 (2)	C16—N2—C12—C13	−0.5 (3)
C10—N1—C9—C8	−179.60 (14)	N2—C12—C13—C14	0.1 (3)
O1—C2—C3—C4	179.77 (13)	C15—C14—C13—C12	−0.2 (3)

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

(MRE_TMP_22TP)

Crystal data

C30H34N2O4S2	Z = 2
Mr = 550.71	F(000) = 584
Monoclinic, P21/n	Dx = 1.334 Mg m^−3
a = 7.7971 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 22.217 (5) Å	µ = 0.23 mm^−1
c = 7.9179 (15) Å	T = 150 K
β = 91.479 (15)°	Block, colorless
V = 1371.1 (5) Å^3	0.45 × 0.31 × 0.21 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2870 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.080
profile data from ω–scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −10→10
Tmin = 0.843, Tmax = 1.000	k = −28→28
13884 measured reflections	l = −10→10
3151 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) = 0.168	w = 1/[σ^2(Fo^2) + (0.0892P)^2 + 0.8922P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
3151 reflections	Δρmax = 0.83 e Å^−3
177 parameters	Δρmin = −0.47 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
S1	0.25411 (7)	0.00844 (3)	0.62304 (7)	0.0358 (2)
C9	0.8457 (2)	−0.00939 (8)	0.9228 (2)	0.0202 (4)
N1	0.89884 (19)	0.04747 (7)	0.94647 (19)	0.0208 (3)
C10	0.9482 (2)	−0.05757 (8)	0.9778 (2)	0.0206 (4)
C14	0.0295 (3)	0.08624 (9)	0.5130 (3)	0.0344 (5)
H14	−0.0715	0.1043	0.4661	0.041*
C8	0.6731 (2)	−0.01900 (10)	0.8389 (3)	0.0305 (4)
H8A	0.6271	0.0197	0.7994	0.046*
H8B	0.5949	−0.0368	0.9200	0.046*
H8C	0.6847	−0.0462	0.7424	0.046*
C15	0.0574 (2)	0.02396 (9)	0.5272 (2)	0.0261 (4)
C13	0.1754 (3)	0.11887 (10)	0.5797 (3)	0.0369 (5)
H13	0.1820	0.1616	0.5798	0.044*
C11	0.8929 (3)	−0.12172 (9)	0.9532 (3)	0.0311 (4)
H11A	0.9822	−0.1487	0.9989	0.047*
H11B	0.8746	−0.1297	0.8324	0.047*
H11C	0.7858	−0.1287	1.0123	0.047*
C12	0.3030 (3)	0.08311 (11)	0.6424 (3)	0.0373 (5)
H12	0.4072	0.0979	0.6914	0.045*
O1	0.68599 (17)	0.14377 (6)	0.86376 (16)	0.0243 (3)
H1	0.7429	0.1130	0.8913	0.036*
O2	0.33099 (18)	0.29239 (6)	1.09693 (18)	0.0280 (3)
H2	0.2945	0.3048	1.1895	0.042*
C5	0.4543 (2)	0.21723 (9)	1.2833 (2)	0.0264 (4)
H5	0.4023	0.2347	1.3788	0.032*
C2	0.6091 (2)	0.16711 (7)	1.0045 (2)	0.0198 (4)
C6	0.4294 (2)	0.24233 (8)	1.1239 (2)	0.0217 (4)
C1	0.5032 (2)	0.21735 (8)	0.9803 (2)	0.0205 (4)
C3	0.6347 (2)	0.14117 (8)	1.1633 (2)	0.0238 (4)
H3	0.7055	0.1066	1.1766	0.029*
C7	0.4673 (3)	0.24375 (9)	0.8081 (2)	0.0283 (4)
H7A	0.5400	0.2792	0.7924	0.043*
H7B	0.3463	0.2556	0.7982	0.043*
H7C	0.4921	0.2137	0.7215	0.043*
C4	0.5562 (2)	0.16612 (9)	1.3014 (2)	0.0272 (4)
H4	0.5721	0.1482	1.4096	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0335 (3)	0.0343 (3)	0.0395 (3)	0.0026 (2)	−0.0030 (2)	0.0078 (2)
C9	0.0170 (8)	0.0222 (8)	0.0215 (8)	0.0001 (6)	0.0024 (6)	−0.0015 (6)
N1	0.0199 (7)	0.0196 (7)	0.0229 (7)	0.0021 (5)	0.0035 (6)	−0.0007 (5)
C10	0.0207 (8)	0.0174 (8)	0.0239 (8)	−0.0005 (6)	0.0046 (6)	−0.0024 (6)
C14	0.0484 (13)	0.0236 (10)	0.0310 (10)	−0.0053 (9)	−0.0016 (9)	0.0027 (8)
C8	0.0192 (9)	0.0327 (10)	0.0395 (11)	−0.0011 (7)	−0.0037 (8)	−0.0047 (8)
C15	0.0253 (9)	0.0276 (9)	0.0256 (9)	0.0050 (8)	0.0048 (7)	0.0027 (7)
C13	0.0378 (11)	0.0287 (10)	0.0440 (12)	−0.0017 (9)	−0.0013 (9)	0.0030 (9)
C11	0.0305 (10)	0.0212 (9)	0.0417 (11)	−0.0039 (8)	0.0023 (8)	−0.0037 (8)
C12	0.0364 (11)	0.0383 (12)	0.0370 (11)	−0.0016 (9)	−0.0024 (9)	0.0040 (9)
O1	0.0273 (7)	0.0209 (6)	0.0250 (7)	0.0071 (5)	0.0056 (5)	0.0034 (5)
O2	0.0299 (7)	0.0251 (7)	0.0295 (7)	0.0078 (5)	0.0070 (6)	−0.0005 (5)
C5	0.0244 (9)	0.0307 (10)	0.0244 (9)	−0.0023 (7)	0.0040 (7)	−0.0024 (7)
C2	0.0183 (8)	0.0182 (8)	0.0229 (8)	−0.0023 (6)	0.0025 (6)	0.0014 (6)
C6	0.0191 (8)	0.0191 (8)	0.0270 (9)	−0.0025 (6)	0.0028 (6)	−0.0011 (6)
C1	0.0188 (8)	0.0188 (8)	0.0241 (8)	−0.0016 (6)	0.0024 (6)	0.0024 (6)
C3	0.0213 (8)	0.0227 (8)	0.0272 (9)	−0.0006 (7)	0.0010 (7)	0.0051 (7)
C7	0.0324 (10)	0.0264 (9)	0.0264 (9)	0.0089 (8)	0.0036 (7)	0.0050 (7)
C4	0.0275 (9)	0.0313 (10)	0.0227 (9)	−0.0043 (8)	0.0005 (7)	0.0054 (7)

Geometric parameters (Å, º)

S1—C12	1.708 (2)	C11—H11C	0.9800
S1—C15	1.728 (2)	C12—H12	0.9500
C9—N1	1.341 (2)	O1—C2	1.380 (2)
C9—C10	1.398 (2)	O1—H1	0.8400
C9—C8	1.501 (3)	O2—C6	1.365 (2)
N1—C10^i	1.340 (2)	O2—H2	0.8400
C10—N1^i	1.340 (2)	C5—C6	1.390 (3)
C10—C11	1.500 (2)	C5—C4	1.391 (3)
C14—C15	1.405 (3)	C5—H5	0.9500
C14—C13	1.438 (3)	C2—C3	1.393 (2)
C14—H14	0.9500	C2—C1	1.398 (2)
C8—H8A	0.9800	C6—C1	1.402 (2)
C8—H8B	0.9800	C1—C7	1.504 (2)
C8—H8C	0.9800	C3—C4	1.382 (3)
C15—C15^ii	1.449 (4)	C3—H3	0.9500
C13—C12	1.357 (3)	C7—H7A	0.9800
C13—H13	0.9500	C7—H7B	0.9800
C11—H11A	0.9800	C7—H7C	0.9800
C11—H11B	0.9800	C4—H4	0.9500
C12—S1—C15	92.24 (10)	C13—C12—S1	112.09 (18)
N1—C9—C10	120.39 (16)	C13—C12—H12	124.0
N1—C9—C8	117.76 (16)	S1—C12—H12	124.0
C10—C9—C8	121.84 (17)	C2—O1—H1	109.5
C10^i—N1—C9	119.23 (15)	C6—O2—H2	109.5
N1^i—C10—C9	120.38 (16)	C6—C5—C4	119.13 (17)
N1^i—C10—C11	117.82 (16)	C6—C5—H5	120.4
C9—C10—C11	121.79 (17)	C4—C5—H5	120.4
C15—C14—C13	110.3 (2)	O1—C2—C3	121.21 (15)
C15—C14—H14	124.8	O1—C2—C1	117.17 (15)
C13—C14—H14	124.8	C3—C2—C1	121.61 (16)
C9—C8—H8A	109.5	O2—C6—C5	122.26 (17)
C9—C8—H8B	109.5	O2—C6—C1	115.91 (16)
H8A—C8—H8B	109.5	C5—C6—C1	121.83 (17)
C9—C8—H8C	109.5	C2—C1—C6	117.28 (16)
H8A—C8—H8C	109.5	C2—C1—C7	122.06 (16)
H8B—C8—H8C	109.5	C6—C1—C7	120.66 (16)
C14—C15—C15^ii	127.4 (2)	C4—C3—C2	119.48 (17)
C14—C15—S1	111.44 (16)	C4—C3—H3	120.3
C15^ii—C15—S1	121.21 (19)	C2—C3—H3	120.3
C12—C13—C14	113.9 (2)	C1—C7—H7A	109.5
C12—C13—H13	123.1	C1—C7—H7B	109.5
C14—C13—H13	123.1	H7A—C7—H7B	109.5
C10—C11—H11A	109.5	C1—C7—H7C	109.5
C10—C11—H11B	109.5	H7A—C7—H7C	109.5
H11A—C11—H11B	109.5	H7B—C7—H7C	109.5
C10—C11—H11C	109.5	C3—C4—C5	120.62 (17)
H11A—C11—H11C	109.5	C3—C4—H4	119.7
H11B—C11—H11C	109.5	C5—C4—H4	119.7
C10—C9—N1—C10^i	0.5 (3)	C4—C5—C6—C1	0.4 (3)
C8—C9—N1—C10^i	179.52 (16)	O1—C2—C1—C6	−177.99 (15)
N1—C9—C10—N1^i	−0.5 (3)	C3—C2—C1—C6	2.7 (3)
C8—C9—C10—N1^i	−179.48 (17)	O1—C2—C1—C7	2.6 (2)
N1—C9—C10—C11	−179.91 (17)	C3—C2—C1—C7	−176.72 (17)
C8—C9—C10—C11	1.1 (3)	O2—C6—C1—C2	178.07 (15)
C13—C14—C15—C15^ii	−179.1 (2)	C5—C6—C1—C2	−2.4 (3)
C13—C14—C15—S1	1.2 (2)	O2—C6—C1—C7	−2.5 (2)
C12—S1—C15—C14	−0.90 (17)	C5—C6—C1—C7	177.09 (17)
C12—S1—C15—C15^ii	179.5 (2)	O1—C2—C3—C4	179.58 (16)
C15—C14—C13—C12	−1.1 (3)	C1—C2—C3—C4	−1.2 (3)
C14—C13—C12—S1	0.4 (3)	C2—C3—C4—C5	−0.9 (3)
C15—S1—C12—C13	0.3 (2)	C6—C5—C4—C3	1.2 (3)
C4—C5—C6—O2	179.99 (17)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2^iii	0.95	2.64	3.187 (3)	117
O1—H1···N1	0.84	1.94	2.776 (2)	173
O2—H2···O1^iv	0.84	2.00	2.8065 (19)	162
C3—H3···S1^v	0.95	3.02	3.819 (2)	143

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

(MRE_TMP_ACR)

Crystal data

C43H49N5O4	V = 969 (2) Å^3
Mr = 699.87	Z = 1
Triclinic, P1	F(000) = 374
a = 7.409 (10) Å	Dx = 1.200 Mg m^−3
b = 8.781 (11) Å	Mo Kα radiation, λ = 0.71073 Å
c = 15.360 (19) Å	µ = 0.08 mm^−1
α = 81.63 (3)°	T = 150 K
β = 86.57 (3)°	Block, green
γ = 78.64 (2)°	0.44 × 0.26 × 0.19 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	1972 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.163
profile data from ω–scans	θmax = 27.0°, θmin = 1.3°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.44, Tmax = 1.000	k = −11→11
9995 measured reflections	l = −19→19
4227 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)] = 0.080	H-atom parameters constrained
wR(F^2) = 0.250	w = 1/[σ^2(Fo^2) + (0.1039P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
4227 reflections	Δρmax = 0.34 e Å^−3
251 parameters	Δρmin = −0.34 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C22	−0.0571 (4)	0.9734 (4)	0.0880 (3)	0.0582 (9)
C20	−0.0659 (4)	1.1281 (4)	0.0426 (3)	0.0564 (9)
C19	−0.1339 (5)	1.2570 (5)	0.0906 (3)	0.0813 (13)
H19	−0.1403	1.3616	0.0624	0.098*
C16	−0.1173 (5)	0.9519 (6)	0.1780 (3)	0.0819 (12)
H16	−0.1136	0.8488	0.2080	0.098*
C18	−0.1890 (6)	1.2298 (8)	0.1761 (4)	0.1041 (18)
H18	−0.2353	1.3166	0.2067	0.125*
C17	−0.1799 (6)	1.0767 (8)	0.2213 (3)	0.1017 (16)
H17	−0.2174	1.0614	0.2817	0.122*
N3	0.0095 (19)	0.8483 (12)	0.0385 (11)	0.054 (5)	0.5
C23	0.004 (3)	0.847 (2)	0.0489 (14)	0.072 (7)	0.5
H23	0.0071	0.7443	0.0796	0.086*	0.5
N1	0.1431 (3)	0.0795 (3)	0.48262 (16)	0.0479 (6)
C1	0.4970 (4)	0.4661 (3)	0.32667 (19)	0.0396 (6)
C2	0.3692 (4)	0.3694 (3)	0.35482 (19)	0.0426 (7)
O1	0.4126 (3)	0.2630 (3)	0.42821 (16)	0.0673 (7)
H1	0.3287	0.2106	0.4401	0.101*
O2	0.5850 (3)	0.6681 (3)	0.22581 (17)	0.0642 (7)
H2	0.5454	0.7344	0.1828	0.096*
C6	0.4566 (4)	0.5747 (3)	0.25245 (19)	0.0426 (7)
C5	0.2964 (4)	0.5891 (3)	0.2077 (2)	0.0509 (8)
H5	0.2718	0.6647	0.1568	0.061*
C3	0.2078 (4)	0.3825 (3)	0.3103 (2)	0.0469 (7)
H3	0.1228	0.3159	0.3301	0.056*
C10	0.1494 (4)	−0.0556 (3)	0.45094 (19)	0.0452 (7)
C4	0.1727 (4)	0.4931 (3)	0.2372 (2)	0.0520 (8)
H4	0.0621	0.5035	0.2067	0.062*
C9	−0.0031 (5)	0.1357 (3)	0.5312 (2)	0.0477 (7)
C7	0.6695 (4)	0.4513 (4)	0.3768 (2)	0.0579 (9)
H7A	0.7541	0.5107	0.3419	0.087*
H7B	0.7288	0.3406	0.3885	0.087*
H7C	0.6378	0.4929	0.4328	0.087*
C11	0.3184 (5)	−0.1144 (4)	0.3985 (3)	0.0722 (11)
H11A	0.3895	−0.0307	0.3829	0.108*
H11B	0.2829	−0.1471	0.3447	0.108*
H11C	0.3939	−0.2041	0.4335	0.108*
C8	−0.0013 (6)	0.2864 (4)	0.5667 (3)	0.0746 (11)
H8A	0.0955	0.3369	0.5357	0.112*
H8B	0.0228	0.2638	0.6298	0.112*
H8C	−0.1211	0.3565	0.5577	0.112*
N2	0.4979 (3)	0.8877 (3)	0.07258 (16)	0.0445 (6)
C13	0.4340 (4)	1.0395 (3)	0.07898 (19)	0.0430 (7)
C14	0.5640 (4)	0.8474 (3)	−0.0059 (2)	0.0456 (7)
C15	0.6336 (5)	0.6763 (3)	−0.0097 (3)	0.0706 (11)
H15A	0.7681	0.6565	−0.0174	0.106*
H15B	0.5796	0.6450	−0.0594	0.106*
H15C	0.5987	0.6155	0.0452	0.106*
C12	0.3603 (5)	1.0792 (4)	0.1680 (2)	0.0667 (10)
H12A	0.3872	0.9855	0.2119	0.100*
H12B	0.2268	1.1166	0.1659	0.100*
H12C	0.4189	1.1614	0.1843	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C22	0.0461 (19)	0.062 (2)	0.066 (3)	−0.0022 (16)	−0.0163 (16)	−0.0124 (19)
C20	0.0425 (18)	0.057 (2)	0.068 (3)	0.0035 (14)	−0.0147 (17)	−0.0157 (17)
C19	0.061 (2)	0.074 (3)	0.108 (4)	0.0100 (18)	−0.017 (2)	−0.035 (2)
C16	0.066 (2)	0.118 (4)	0.063 (3)	−0.021 (2)	−0.014 (2)	−0.006 (2)
C18	0.061 (3)	0.148 (5)	0.112 (5)	0.002 (3)	−0.002 (3)	−0.075 (4)
C17	0.066 (3)	0.175 (6)	0.069 (4)	−0.021 (3)	−0.004 (2)	−0.037 (4)
N3	0.051 (7)	0.021 (4)	0.085 (11)	0.010 (4)	−0.011 (6)	−0.012 (5)
C23	0.057 (10)	0.114 (14)	0.042 (8)	−0.027 (8)	−0.030 (7)	0.023 (7)
N1	0.0616 (16)	0.0418 (14)	0.0427 (17)	−0.0199 (11)	−0.0032 (12)	0.0011 (10)
C1	0.0403 (15)	0.0387 (15)	0.0397 (18)	−0.0079 (11)	−0.0006 (12)	−0.0048 (11)
C2	0.0481 (16)	0.0414 (16)	0.0391 (18)	−0.0130 (12)	−0.0039 (13)	−0.0008 (12)
O1	0.0735 (16)	0.0718 (16)	0.0582 (17)	−0.0363 (12)	−0.0183 (12)	0.0236 (11)
O2	0.0603 (14)	0.0688 (16)	0.0607 (18)	−0.0265 (11)	−0.0098 (11)	0.0229 (11)
C6	0.0438 (16)	0.0390 (15)	0.0436 (19)	−0.0076 (12)	0.0028 (13)	−0.0030 (12)
C5	0.0518 (18)	0.0541 (18)	0.043 (2)	−0.0073 (13)	−0.0077 (14)	0.0040 (13)
C3	0.0478 (17)	0.0505 (17)	0.047 (2)	−0.0197 (13)	−0.0030 (13)	−0.0066 (13)
C10	0.0635 (19)	0.0413 (16)	0.0295 (17)	−0.0112 (13)	−0.0023 (13)	0.0014 (11)
C4	0.0468 (17)	0.0601 (19)	0.050 (2)	−0.0089 (14)	−0.0144 (14)	−0.0079 (14)
C9	0.073 (2)	0.0360 (15)	0.0357 (18)	−0.0154 (14)	−0.0050 (14)	−0.0012 (11)
C7	0.0539 (19)	0.070 (2)	0.051 (2)	−0.0222 (15)	−0.0140 (15)	0.0057 (15)
C11	0.082 (3)	0.074 (2)	0.055 (2)	−0.0093 (19)	0.0154 (19)	−0.0066 (17)
C8	0.113 (3)	0.048 (2)	0.071 (3)	−0.0245 (19)	−0.008 (2)	−0.0212 (17)
N2	0.0483 (14)	0.0439 (14)	0.0388 (16)	−0.0093 (10)	−0.0011 (11)	0.0032 (10)
C13	0.0427 (16)	0.0474 (17)	0.0389 (18)	−0.0078 (12)	0.0003 (12)	−0.0072 (12)
C14	0.0451 (16)	0.0370 (15)	0.053 (2)	−0.0058 (11)	−0.0039 (13)	−0.0026 (12)
C15	0.082 (2)	0.0380 (18)	0.090 (3)	−0.0060 (16)	−0.004 (2)	−0.0083 (16)
C12	0.070 (2)	0.081 (2)	0.046 (2)	−0.0063 (18)	0.0056 (17)	−0.0141 (17)

Geometric parameters (Å, º)

C22—C23	1.33 (2)	C5—H5	0.9500
C22—N3	1.420 (13)	C3—C4	1.375 (4)
C22—C16	1.424 (6)	C3—H3	0.9500
C22—C20	1.424 (5)	C10—C9^ii	1.399 (4)
C20—N3^i	1.291 (17)	C10—C11	1.493 (5)
C20—C19	1.433 (5)	C4—H4	0.9500
C20—C23^i	1.45 (2)	C9—C10^ii	1.399 (4)
C19—C18	1.354 (7)	C9—C8	1.504 (4)
C19—H19	0.9500	C7—H7A	0.9800
C16—C17	1.354 (7)	C7—H7B	0.9800
C16—H16	0.9500	C7—H7C	0.9800
C18—C17	1.411 (7)	C11—H11A	0.9800
C18—H18	0.9500	C11—H11B	0.9800
C17—H17	0.9500	C11—H11C	0.9800
N3—C20^i	1.291 (17)	C8—H8A	0.9800
C23—C20^i	1.45 (2)	C8—H8B	0.9800
C23—H23	0.9500	C8—H8C	0.9800
N1—C9	1.332 (4)	N2—C13	1.339 (4)
N1—C10	1.337 (4)	N2—C14	1.343 (4)
C1—C6	1.382 (4)	C13—C14^iii	1.388 (4)
C1—C2	1.402 (4)	C13—C12	1.505 (5)
C1—C7	1.506 (4)	C14—C13^iii	1.388 (4)
C2—O1	1.366 (4)	C14—C15	1.498 (4)
C2—C3	1.390 (4)	C15—H15A	0.9800
O1—H1	0.8400	C15—H15B	0.9800
O2—C6	1.381 (3)	C15—H15C	0.9800
O2—H2	0.8400	C12—H12A	0.9800
C6—C5	1.382 (4)	C12—H12B	0.9800
C5—C4	1.378 (4)	C12—H12C	0.9800
C23—C22—N3	5.6 (15)	N1—C10—C9^ii	119.9 (3)
C23—C22—C16	118.2 (11)	N1—C10—C11	116.9 (3)
N3—C22—C16	123.8 (7)	C9^ii—C10—C11	123.2 (3)
C23—C22—C20	122.1 (11)	C3—C4—C5	120.6 (3)
N3—C22—C20	116.5 (7)	C3—C4—H4	119.7
C16—C22—C20	119.6 (4)	C5—C4—H4	119.7
N3^i—C20—C22	121.2 (6)	N1—C9—C10^ii	120.7 (3)
N3^i—C20—C19	120.8 (5)	N1—C9—C8	117.1 (3)
C22—C20—C19	117.9 (4)	C10^ii—C9—C8	122.1 (3)
N3^i—C20—C23^i	0.8 (13)	C1—C7—H7A	109.5
C22—C20—C23^i	120.7 (8)	C1—C7—H7B	109.5
C19—C20—C23^i	121.4 (9)	H7A—C7—H7B	109.5
C18—C19—C20	120.0 (4)	C1—C7—H7C	109.5
C18—C19—H19	120.0	H7A—C7—H7C	109.5
C20—C19—H19	120.0	H7B—C7—H7C	109.5
C17—C16—C22	120.7 (5)	C10—C11—H11A	109.5
C17—C16—H16	119.6	C10—C11—H11B	109.5
C22—C16—H16	119.6	H11A—C11—H11B	109.5
C19—C18—C17	122.2 (5)	C10—C11—H11C	109.5
C19—C18—H18	118.9	H11A—C11—H11C	109.5
C17—C18—H18	118.9	H11B—C11—H11C	109.5
C16—C17—C18	119.5 (5)	C9—C8—H8A	109.5
C16—C17—H17	120.2	C9—C8—H8B	109.5
C18—C17—H17	120.2	H8A—C8—H8B	109.5
C20^i—N3—C22	122.2 (9)	C9—C8—H8C	109.5
C22—C23—C20^i	117.2 (16)	H8A—C8—H8C	109.5
C22—C23—H23	121.4	H8B—C8—H8C	109.5
C20^i—C23—H23	121.4	C13—N2—C14	118.6 (2)
C9—N1—C10	119.3 (2)	N2—C13—C14^iii	120.6 (3)
C6—C1—C2	117.3 (3)	N2—C13—C12	116.8 (3)
C6—C1—C7	122.2 (2)	C14^iii—C13—C12	122.5 (3)
C2—C1—C7	120.5 (3)	N2—C14—C13^iii	120.8 (3)
O1—C2—C3	122.4 (2)	N2—C14—C15	116.6 (3)
O1—C2—C1	116.1 (3)	C13^iii—C14—C15	122.6 (3)
C3—C2—C1	121.4 (3)	C14—C15—H15A	109.5
C2—O1—H1	109.5	C14—C15—H15B	109.5
C6—O2—H2	109.5	H15A—C15—H15B	109.5
O2—C6—C1	116.3 (3)	C14—C15—H15C	109.5
O2—C6—C5	122.0 (3)	H15A—C15—H15C	109.5
C1—C6—C5	121.8 (3)	H15B—C15—H15C	109.5
C4—C5—C6	119.6 (3)	C13—C12—H12A	109.5
C4—C5—H5	120.2	C13—C12—H12B	109.5
C6—C5—H5	120.2	H12A—C12—H12B	109.5
C4—C3—C2	119.2 (3)	C13—C12—H12C	109.5
C4—C3—H3	120.4	H12A—C12—H12C	109.5
C2—C3—H3	120.4	H12B—C12—H12C	109.5
C23—C22—C20—N3^i	−2.0 (6)	C20—C22—C23—C20^i	1.2 (17)
N3—C22—C20—N3^i	−2.5 (14)	C6—C1—C2—O1	179.9 (3)
C16—C22—C20—N3^i	178.8 (8)	C7—C1—C2—O1	−0.7 (4)
C23—C22—C20—C19	−180.0 (10)	C6—C1—C2—C3	−0.3 (4)
N3—C22—C20—C19	179.5 (6)	C7—C1—C2—C3	179.1 (3)
C16—C22—C20—C19	0.8 (5)	C2—C1—C6—O2	−179.8 (2)
C23—C22—C20—C23^i	−1.3 (18)	C7—C1—C6—O2	0.9 (4)
N3—C22—C20—C23^i	−1.8 (6)	C2—C1—C6—C5	0.4 (4)
C16—C22—C20—C23^i	179.5 (8)	C7—C1—C6—C5	−178.9 (3)
N3^i—C20—C19—C18	−178.6 (8)	O2—C6—C5—C4	−179.8 (3)
C22—C20—C19—C18	−0.7 (5)	C1—C6—C5—C4	−0.1 (5)
C23^i—C20—C19—C18	−179.4 (9)	O1—C2—C3—C4	179.6 (3)
C23—C22—C16—C17	179.6 (9)	C1—C2—C3—C4	−0.2 (4)
N3—C22—C16—C17	−179.8 (7)	C9—N1—C10—C9^ii	0.2 (5)
C20—C22—C16—C17	−1.1 (5)	C9—N1—C10—C11	−178.7 (3)
C20—C19—C18—C17	0.9 (6)	C2—C3—C4—C5	0.6 (5)
C22—C16—C17—C18	1.3 (6)	C6—C5—C4—C3	−0.5 (5)
C19—C18—C17—C16	−1.2 (7)	C10—N1—C9—C10^ii	−0.3 (5)
C23—C22—N3—C20^i	−173 (14)	C10—N1—C9—C8	178.8 (3)
C16—C22—N3—C20^i	−178.8 (7)	C14—N2—C13—C14^iii	0.1 (4)
C20—C22—N3—C20^i	2.5 (14)	C14—N2—C13—C12	179.7 (3)
N3—C22—C23—C20^i	6 (12)	C13—N2—C14—C13^iii	−0.1 (4)
C16—C22—C23—C20^i	−179.5 (8)	C13—N2—C14—C15	−179.9 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.99	2.821 (4)	173
O2—H2···N2	0.84	2.01	2.836 (4)	170
C11—H11C···O1^iv	0.98	2.57	3.370 (6)	139

Symmetry code: (iv) −x+1, −y, −z+1.

(MRE_TMP_ANT)

Crystal data

C29H30N2O2	Z = 4
Mr = 438.55	F(000) = 936
Monoclinic, P21/c	Dx = 1.236 Mg m^−3
a = 7.5571 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 24.125 (2) Å	µ = 0.08 mm^−1
c = 12.9363 (13) Å	T = 150 K
β = 92.034 (4)°	Block, colorless
V = 2356.9 (4) Å^3	0.45 × 0.37 × 0.18 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	4396 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.116
profile data from ω–scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.829, Tmax = 1.000	k = −31→31
24797 measured reflections	l = −16→16
5411 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)] = 0.068	H-atom parameters constrained
wR(F^2) = 0.205	w = 1/[σ^2(Fo^2) + (0.097P)^2 + 0.2524P] where P = (Fo^2 + 2Fc^2)/3
S = 1.18	(Δ/σ)max < 0.001
5411 reflections	Δρmax = 0.42 e Å^−3
305 parameters	Δρmin = −0.50 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
N1	0.11069 (19)	0.32214 (6)	0.24426 (11)	0.0268 (3)
O1	0.25713 (17)	0.21837 (5)	0.21642 (11)	0.0368 (3)
H1	0.2050	0.2488	0.2241	0.055*
O2	0.16046 (18)	0.02652 (5)	0.22167 (12)	0.0412 (4)
H2	0.0845	0.0025	0.2356	0.062*
N2	0.0430 (2)	0.43409 (6)	0.24585 (12)	0.0296 (3)
C6	0.0933 (2)	0.07805 (7)	0.23876 (13)	0.0275 (4)
C1	0.2059 (2)	0.12230 (7)	0.21789 (12)	0.0243 (4)
C11	0.0399 (2)	0.34711 (7)	0.15990 (13)	0.0270 (4)
C8	0.1474 (2)	0.35190 (7)	0.32966 (13)	0.0261 (4)
C10	0.0052 (2)	0.40417 (7)	0.16084 (13)	0.0280 (4)
C9	0.1146 (2)	0.40902 (7)	0.33006 (13)	0.0275 (4)
C2	0.1434 (2)	0.17590 (7)	0.23537 (13)	0.0264 (4)
C12	0.2217 (3)	0.32197 (8)	0.42320 (15)	0.0367 (4)
H12A	0.2357	0.2826	0.4069	0.055*
H12B	0.1406	0.3260	0.4802	0.055*
H12C	0.3371	0.3378	0.4436	0.055*
C3	−0.0252 (2)	0.18512 (7)	0.27210 (14)	0.0309 (4)
H3	−0.0660	0.2218	0.2831	0.037*
C7	0.3890 (2)	0.11209 (7)	0.18060 (15)	0.0316 (4)
H7A	0.4638	0.0971	0.2374	0.047*
H7B	0.4395	0.1471	0.1568	0.047*
H7C	0.3832	0.0855	0.1233	0.047*
C5	−0.0752 (2)	0.08643 (8)	0.27605 (13)	0.0313 (4)
H5	−0.1495	0.0558	0.2901	0.038*
C4	−0.1328 (2)	0.14009 (8)	0.29234 (14)	0.0331 (4)
H4	−0.2476	0.1462	0.3177	0.040*
C15	−0.0027 (3)	0.31195 (9)	0.06647 (15)	0.0380 (5)
H15A	0.0447	0.2745	0.0778	0.057*
H15B	0.0510	0.3284	0.0058	0.057*
H15C	−0.1314	0.3100	0.0549	0.057*
C13	0.1586 (3)	0.44442 (8)	0.42263 (16)	0.0411 (5)
H13A	0.1100	0.4817	0.4114	0.062*
H13B	0.2875	0.4467	0.4330	0.062*
H13C	0.1071	0.4280	0.4840	0.062*
C14	−0.0723 (3)	0.43380 (9)	0.06771 (15)	0.0403 (5)
H14A	−0.0985	0.4723	0.0860	0.061*
H14B	−0.1817	0.4152	0.0441	0.061*
H14C	0.0127	0.4332	0.0123	0.061*
C22	0.4055 (2)	0.68969 (8)	0.77034 (15)	0.0338 (4)
H22	0.3921	0.7287	0.7759	0.041*
C23	0.4733 (2)	0.65993 (8)	0.85528 (14)	0.0316 (4)
C29	0.4484 (3)	0.57486 (8)	0.75360 (14)	0.0341 (4)
H29	0.4641	0.5359	0.7476	0.041*
C16	0.3777 (2)	0.60464 (8)	0.66886 (14)	0.0321 (4)
C21	0.3568 (2)	0.66351 (8)	0.67727 (14)	0.0316 (4)
C17	0.3266 (3)	0.57818 (10)	0.57370 (15)	0.0417 (5)
H17	0.3375	0.5391	0.5675	0.050*
C28	0.4960 (2)	0.60103 (8)	0.84651 (14)	0.0319 (4)
C27	0.5646 (3)	0.57103 (9)	0.93493 (15)	0.0403 (5)
H27	0.5837	0.5322	0.9299	0.048*
C19	0.2438 (3)	0.66654 (11)	0.49923 (16)	0.0473 (6)
H19	0.1999	0.6871	0.4411	0.057*
C26	0.6026 (3)	0.59755 (11)	1.02582 (16)	0.0458 (5)
H26	0.6458	0.5770	1.0840	0.055*
C18	0.2623 (3)	0.60842 (11)	0.49166 (16)	0.0473 (6)
H18	0.2296	0.5902	0.4287	0.057*
C20	0.2882 (3)	0.69333 (10)	0.58883 (15)	0.0405 (5)
H20	0.2735	0.7324	0.5929	0.049*
C24	0.5183 (3)	0.68582 (10)	0.95219 (16)	0.0408 (5)
H24	0.5058	0.7248	0.9590	0.049*
C25	0.5785 (3)	0.65553 (11)	1.03455 (16)	0.0463 (5)
H25	0.6048	0.6734	1.0987	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0311 (7)	0.0203 (7)	0.0293 (7)	−0.0001 (5)	0.0028 (6)	−0.0003 (5)
O1	0.0402 (7)	0.0182 (6)	0.0525 (9)	−0.0006 (5)	0.0084 (6)	−0.0003 (6)
O2	0.0453 (8)	0.0185 (6)	0.0601 (9)	−0.0022 (5)	0.0071 (7)	−0.0014 (6)
N2	0.0353 (8)	0.0218 (7)	0.0318 (8)	0.0026 (6)	0.0019 (6)	−0.0002 (6)
C6	0.0348 (9)	0.0229 (8)	0.0246 (8)	0.0001 (7)	−0.0033 (7)	0.0004 (6)
C1	0.0303 (8)	0.0219 (8)	0.0204 (8)	0.0003 (6)	−0.0029 (6)	−0.0002 (6)
C11	0.0290 (8)	0.0271 (8)	0.0252 (8)	−0.0017 (7)	0.0032 (6)	−0.0013 (6)
C8	0.0281 (8)	0.0246 (8)	0.0256 (8)	0.0002 (6)	0.0028 (6)	0.0006 (6)
C10	0.0291 (8)	0.0269 (9)	0.0280 (9)	0.0025 (7)	0.0026 (7)	0.0033 (7)
C9	0.0303 (8)	0.0255 (8)	0.0266 (8)	0.0015 (6)	0.0011 (7)	−0.0020 (6)
C2	0.0328 (9)	0.0219 (8)	0.0245 (8)	−0.0007 (6)	−0.0015 (7)	−0.0003 (6)
C12	0.0409 (10)	0.0397 (10)	0.0294 (9)	0.0062 (8)	−0.0009 (8)	0.0077 (8)
C3	0.0356 (9)	0.0277 (9)	0.0294 (9)	0.0055 (7)	−0.0002 (7)	−0.0036 (7)
C7	0.0335 (9)	0.0286 (9)	0.0328 (9)	0.0010 (7)	0.0036 (7)	−0.0022 (7)
C5	0.0347 (9)	0.0315 (9)	0.0277 (9)	−0.0078 (7)	−0.0004 (7)	0.0007 (7)
C4	0.0297 (9)	0.0412 (10)	0.0284 (9)	−0.0005 (7)	0.0022 (7)	−0.0033 (7)
C15	0.0413 (10)	0.0408 (11)	0.0318 (10)	−0.0017 (8)	0.0010 (8)	−0.0119 (8)
C13	0.0482 (11)	0.0360 (10)	0.0388 (11)	0.0020 (9)	−0.0034 (9)	−0.0127 (8)
C14	0.0473 (11)	0.0423 (11)	0.0315 (10)	0.0090 (9)	0.0020 (8)	0.0118 (8)
C22	0.0327 (9)	0.0367 (10)	0.0323 (10)	0.0005 (7)	0.0051 (7)	0.0006 (7)
C23	0.0272 (8)	0.0416 (10)	0.0261 (9)	−0.0039 (7)	0.0025 (7)	−0.0029 (7)
C29	0.0394 (10)	0.0325 (10)	0.0304 (9)	−0.0064 (8)	0.0015 (8)	0.0009 (7)
C16	0.0304 (9)	0.0418 (10)	0.0242 (9)	−0.0083 (8)	0.0039 (7)	−0.0001 (7)
C21	0.0272 (8)	0.0428 (11)	0.0250 (9)	−0.0007 (7)	0.0038 (7)	0.0040 (7)
C17	0.0454 (11)	0.0522 (12)	0.0276 (10)	−0.0142 (9)	0.0018 (8)	−0.0047 (8)
C28	0.0295 (9)	0.0398 (10)	0.0264 (9)	−0.0048 (7)	0.0018 (7)	0.0048 (7)
C27	0.0412 (10)	0.0474 (12)	0.0321 (10)	−0.0020 (9)	−0.0003 (8)	0.0099 (8)
C19	0.0353 (10)	0.0803 (17)	0.0266 (10)	0.0059 (10)	0.0021 (8)	0.0138 (10)
C26	0.0374 (10)	0.0716 (16)	0.0280 (10)	−0.0027 (10)	−0.0044 (8)	0.0097 (10)
C18	0.0392 (11)	0.0783 (17)	0.0244 (10)	−0.0135 (11)	0.0014 (8)	−0.0044 (9)
C20	0.0366 (10)	0.0548 (13)	0.0306 (10)	0.0085 (9)	0.0064 (8)	0.0107 (8)
C24	0.0367 (10)	0.0525 (13)	0.0332 (10)	−0.0050 (9)	0.0025 (8)	−0.0108 (9)
C25	0.0379 (10)	0.0740 (16)	0.0268 (10)	−0.0062 (10)	−0.0030 (8)	−0.0071 (10)

Geometric parameters (Å, º)

N1—C8	1.338 (2)	C5—C4	1.384 (3)
N1—C11	1.341 (2)	C22—C23	1.395 (3)
O1—C2	1.365 (2)	C22—C21	1.397 (3)
O2—C6	1.364 (2)	C23—C24	1.431 (3)
N2—C10	1.338 (2)	C23—C28	1.436 (3)
N2—C9	1.343 (2)	C29—C28	1.394 (3)
C6—C5	1.393 (3)	C29—C16	1.400 (3)
C6—C1	1.397 (2)	C16—C17	1.428 (3)
C1—C2	1.397 (2)	C16—C21	1.434 (3)
C1—C7	1.502 (2)	C21—C20	1.433 (3)
C11—C10	1.401 (2)	C17—C18	1.363 (3)
C11—C15	1.502 (2)	C28—C27	1.435 (3)
C8—C9	1.400 (2)	C27—C26	1.360 (3)
C8—C12	1.501 (2)	C19—C20	1.359 (3)
C10—C14	1.502 (2)	C19—C18	1.413 (4)
C9—C13	1.498 (2)	C26—C25	1.415 (4)
C2—C3	1.394 (3)	C24—C25	1.357 (3)
C3—C4	1.388 (3)
C8—N1—C11	119.73 (14)	C4—C5—C6	119.01 (17)
C10—N2—C9	119.48 (14)	C5—C4—C3	120.92 (17)
O2—C6—C5	122.59 (16)	C23—C22—C21	121.62 (18)
O2—C6—C1	115.63 (15)	C22—C23—C24	122.33 (19)
C5—C6—C1	121.77 (16)	C22—C23—C28	119.26 (16)
C6—C1—C2	117.66 (16)	C24—C23—C28	118.40 (17)
C6—C1—C7	120.72 (15)	C28—C29—C16	121.50 (18)
C2—C1—C7	121.60 (15)	C29—C16—C17	121.98 (19)
N1—C11—C10	120.23 (15)	C29—C16—C21	119.25 (16)
N1—C11—C15	117.96 (16)	C17—C16—C21	118.77 (17)
C10—C11—C15	121.80 (15)	C22—C21—C20	122.53 (19)
N1—C8—C9	119.96 (15)	C22—C21—C16	119.14 (16)
N1—C8—C12	117.92 (15)	C20—C21—C16	118.33 (17)
C9—C8—C12	122.12 (15)	C18—C17—C16	120.7 (2)
N2—C10—C11	120.16 (15)	C29—C28—C27	122.28 (19)
N2—C10—C14	117.95 (16)	C29—C28—C23	119.22 (16)
C11—C10—C14	121.89 (16)	C27—C28—C23	118.49 (17)
N2—C9—C8	120.43 (15)	C26—C27—C28	120.7 (2)
N2—C9—C13	117.60 (16)	C20—C19—C18	120.60 (19)
C8—C9—C13	121.97 (15)	C27—C26—C25	120.66 (19)
O1—C2—C3	122.03 (15)	C17—C18—C19	120.71 (19)
O1—C2—C1	116.56 (15)	C19—C20—C21	120.9 (2)
C3—C2—C1	121.39 (16)	C25—C24—C23	121.0 (2)
C4—C3—C2	119.24 (16)	C24—C25—C26	120.66 (18)

(MRE_TMP_DP)

Crystal data

C34H38N2O4	Z = 2
Mr = 538.66	F(000) = 576
Monoclinic, P21/n	Dx = 1.237 Mg m^−3
a = 8.292 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 20.615 (15) Å	µ = 0.08 mm^−1
c = 8.470 (6) Å	T = 150 K
β = 92.435 (7)°	Block, colorless
V = 1446.7 (18) Å^3	0.49 × 0.34 × 0.25 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2644 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.076
profile data from ω–scans	θmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −10→10
Tmin = 0.640, Tmax = 1.000	k = −26→26
14988 measured reflections	l = −10→11
3328 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)] = 0.065	H-atom parameters constrained
wR(F^2) = 0.214	w = 1/[σ^2(Fo^2) + (0.121P)^2 + 0.2294P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3328 reflections	Δρmax = 0.31 e Å^−3
186 parameters	Δρmin = −0.40 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.12172 (19)	0.14627 (7)	0.18830 (16)	0.0514 (4)
H1	0.0951	0.1159	0.2479	0.077*
O2	−0.10403 (19)	0.29227 (7)	−0.18937 (16)	0.0521 (4)
H2	−0.1936	0.3068	−0.2233	0.078*
C1	−0.0135 (3)	0.17003 (8)	0.10788 (19)	0.0422 (4)
C2	0.0090 (3)	0.21904 (8)	−0.00324 (19)	0.0420 (4)
C3	−0.1283 (3)	0.24347 (8)	−0.08319 (19)	0.0421 (5)
C4	−0.2821 (3)	0.21928 (9)	−0.0583 (2)	0.0474 (5)
H4	−0.3737	0.2359	−0.1161	0.057*
C6	−0.1665 (3)	0.14597 (9)	0.1364 (2)	0.0474 (5)
H6	−0.1793	0.1129	0.2130	0.057*
C17	−0.4697 (2)	−0.01628 (10)	0.4289 (3)	0.0478 (5)
C5	−0.2988 (3)	0.17031 (10)	0.0530 (2)	0.0512 (5)
H5	−0.4030	0.1535	0.0715	0.061*
C7	0.1734 (3)	0.24538 (11)	−0.0364 (3)	0.0598 (6)
H7A	0.1784	0.2552	−0.1493	0.090*
H7B	0.2558	0.2130	−0.0068	0.090*
H7C	0.1931	0.2851	0.0252	0.090*
C16	−0.4549 (4)	−0.08305 (12)	0.4201 (3)	0.0689 (7)
H16	−0.4844	−0.1088	0.5073	0.083*
C12	−0.4244 (4)	0.01865 (13)	0.2991 (4)	0.0936 (12)
H12	−0.4333	0.0646	0.3003	0.112*
C14	−0.3534 (3)	−0.07737 (14)	0.1596 (4)	0.0720 (7)
H14	−0.3144	−0.0977	0.0680	0.086*
C13	−0.3668 (5)	−0.01141 (15)	0.1682 (5)	0.1036 (13)
H13	−0.3356	0.0143	0.0815	0.124*
C15	−0.3978 (4)	−0.11351 (13)	0.2869 (3)	0.0780 (8)
H15	−0.3895	−0.1595	0.2839	0.094*
N1	0.04511 (18)	0.04860 (7)	0.39942 (16)	0.0393 (4)
C8	0.0574 (2)	−0.01365 (9)	0.35683 (18)	0.0364 (4)
C9	−0.0118 (2)	0.06307 (9)	0.54172 (19)	0.0391 (4)
C10	0.1217 (3)	−0.02800 (11)	0.1973 (2)	0.0519 (5)
H10A	0.1480	0.0128	0.1449	0.078*
H10B	0.0398	−0.0514	0.1330	0.078*
H10C	0.2191	−0.0547	0.2102	0.078*
C11	−0.0230 (4)	0.13335 (11)	0.5861 (3)	0.0668 (7)
H11A	0.0635	0.1440	0.6642	0.100*
H11B	−0.1279	0.1417	0.6312	0.100*
H11C	−0.0120	0.1602	0.4918	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0720 (10)	0.0487 (8)	0.0334 (7)	−0.0051 (7)	0.0002 (6)	0.0086 (5)
O2	0.0691 (9)	0.0433 (7)	0.0434 (8)	−0.0103 (6)	−0.0024 (7)	0.0114 (6)
C1	0.0673 (12)	0.0366 (8)	0.0231 (8)	−0.0048 (8)	0.0057 (7)	−0.0036 (6)
C2	0.0660 (12)	0.0347 (8)	0.0251 (8)	−0.0092 (8)	0.0008 (7)	−0.0036 (6)
C3	0.0687 (12)	0.0312 (8)	0.0266 (8)	−0.0093 (8)	0.0033 (8)	−0.0028 (6)
C4	0.0647 (12)	0.0428 (9)	0.0350 (9)	−0.0036 (9)	0.0046 (8)	−0.0014 (7)
C6	0.0699 (13)	0.0416 (9)	0.0318 (9)	−0.0023 (9)	0.0139 (9)	0.0033 (7)
C17	0.0308 (9)	0.0519 (11)	0.0604 (12)	−0.0050 (7)	−0.0002 (8)	0.0183 (9)
C5	0.0646 (13)	0.0472 (10)	0.0428 (10)	−0.0067 (9)	0.0138 (9)	0.0010 (8)
C7	0.0698 (15)	0.0540 (12)	0.0550 (13)	−0.0178 (10)	−0.0055 (10)	0.0133 (10)
C16	0.103 (2)	0.0526 (12)	0.0501 (13)	−0.0141 (12)	−0.0120 (13)	0.0161 (10)
C12	0.119 (3)	0.0544 (14)	0.113 (3)	0.0116 (14)	0.078 (2)	0.0304 (14)
C14	0.0701 (15)	0.0732 (16)	0.0738 (17)	−0.0048 (13)	0.0168 (13)	0.0033 (13)
C13	0.133 (3)	0.0695 (17)	0.115 (3)	0.0103 (17)	0.084 (2)	0.0293 (17)
C15	0.117 (2)	0.0551 (13)	0.0615 (15)	−0.0090 (14)	−0.0064 (15)	0.0041 (11)
N1	0.0470 (9)	0.0467 (8)	0.0241 (7)	0.0061 (6)	0.0015 (6)	0.0031 (6)
C8	0.0372 (8)	0.0489 (9)	0.0229 (7)	0.0092 (7)	0.0008 (6)	−0.0001 (6)
C9	0.0476 (10)	0.0442 (9)	0.0253 (8)	0.0109 (7)	−0.0001 (7)	0.0003 (6)
C10	0.0624 (12)	0.0676 (13)	0.0267 (9)	0.0119 (10)	0.0115 (8)	−0.0020 (8)
C11	0.111 (2)	0.0474 (11)	0.0422 (11)	0.0156 (12)	0.0049 (12)	−0.0030 (9)

Geometric parameters (Å, º)

O1—C1	1.377 (3)	C16—H16	0.9500
O1—H1	0.8400	C12—C13	1.374 (4)
O2—C3	1.370 (2)	C12—H12	0.9500
O2—H2	0.8400	C14—C13	1.366 (4)
C1—C6	1.393 (3)	C14—C15	1.374 (4)
C1—C2	1.399 (2)	C14—H14	0.9500
C2—C3	1.394 (3)	C13—H13	0.9500
C2—C7	1.505 (3)	C15—H15	0.9500
C3—C4	1.393 (3)	N1—C8	1.338 (2)
C4—C5	1.392 (3)	N1—C9	1.346 (2)
C4—H4	0.9500	C8—C9^ii	1.395 (3)
C6—C5	1.374 (3)	C8—C10	1.503 (2)
C6—H6	0.9500	C9—C8^ii	1.395 (3)
C17—C12	1.379 (3)	C9—C11	1.501 (3)
C17—C16	1.384 (3)	C10—H10A	0.9800
C17—C17^i	1.486 (5)	C10—H10B	0.9800
C5—H5	0.9500	C10—H10C	0.9800
C7—H7A	0.9800	C11—H11A	0.9800
C7—H7B	0.9800	C11—H11B	0.9800
C7—H7C	0.9800	C11—H11C	0.9800
C16—C15	1.392 (4)
C1—O1—H1	109.5	C13—C12—C17	121.6 (3)
C3—O2—H2	109.5	C13—C12—H12	119.2
O1—C1—C6	121.06 (16)	C17—C12—H12	119.2
O1—C1—C2	117.46 (18)	C13—C14—C15	118.2 (3)
C6—C1—C2	121.48 (19)	C13—C14—H14	120.9
C3—C2—C1	117.29 (18)	C15—C14—H14	120.9
C3—C2—C7	120.43 (17)	C14—C13—C12	121.6 (3)
C1—C2—C7	122.27 (18)	C14—C13—H13	119.2
O2—C3—C4	121.55 (18)	C12—C13—H13	119.2
O2—C3—C2	116.38 (17)	C14—C15—C16	120.2 (3)
C4—C3—C2	122.07 (17)	C14—C15—H15	119.9
C5—C4—C3	118.7 (2)	C16—C15—H15	119.9
C5—C4—H4	120.7	C8—N1—C9	119.16 (15)
C3—C4—H4	120.7	N1—C8—C9^ii	120.57 (16)
C5—C6—C1	119.61 (18)	N1—C8—C10	117.72 (16)
C5—C6—H6	120.2	C9^ii—C8—C10	121.71 (17)
C1—C6—H6	120.2	N1—C9—C8^ii	120.27 (16)
C12—C17—C16	116.7 (2)	N1—C9—C11	117.76 (17)
C12—C17—C17^i	121.6 (2)	C8^ii—C9—C11	121.97 (17)
C16—C17—C17^i	121.8 (2)	C8—C10—H10A	109.5
C6—C5—C4	120.8 (2)	C8—C10—H10B	109.5
C6—C5—H5	119.6	H10A—C10—H10B	109.5
C4—C5—H5	119.6	C8—C10—H10C	109.5
C2—C7—H7A	109.5	H10A—C10—H10C	109.5
C2—C7—H7B	109.5	H10B—C10—H10C	109.5
H7A—C7—H7B	109.5	C9—C11—H11A	109.5
C2—C7—H7C	109.5	C9—C11—H11B	109.5
H7A—C7—H7C	109.5	H11A—C11—H11B	109.5
H7B—C7—H7C	109.5	C9—C11—H11C	109.5
C17—C16—C15	121.7 (2)	H11A—C11—H11C	109.5
C17—C16—H16	119.1	H11B—C11—H11C	109.5
C15—C16—H16	119.1
O1—C1—C2—C3	−179.33 (14)	C3—C4—C5—C6	−0.3 (3)
C6—C1—C2—C3	0.8 (2)	C12—C17—C16—C15	−0.3 (4)
O1—C1—C2—C7	0.3 (3)	C17^i—C17—C16—C15	−179.9 (3)
C6—C1—C2—C7	−179.61 (17)	C16—C17—C12—C13	−0.3 (5)
C1—C2—C3—O2	178.82 (15)	C17^i—C17—C12—C13	179.3 (3)
C7—C2—C3—O2	−0.8 (2)	C15—C14—C13—C12	−0.6 (6)
C1—C2—C3—C4	−1.9 (3)	C17—C12—C13—C14	0.7 (6)
C7—C2—C3—C4	178.48 (17)	C13—C14—C15—C16	0.1 (5)
O2—C3—C4—C5	−179.07 (17)	C17—C16—C15—C14	0.4 (4)
C2—C3—C4—C5	1.7 (3)	C9—N1—C8—C9^ii	0.0 (3)
O1—C1—C6—C5	−179.37 (17)	C9—N1—C8—C10	−179.88 (16)
C2—C1—C6—C5	0.6 (3)	C8—N1—C9—C8^ii	0.0 (3)
C1—C6—C5—C4	−0.8 (3)	C8—N1—C9—C11	179.64 (18)

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

(MRE_TMP_DPE-I_22BP)

Crystal data

C44H46N6O4	V = 924.6 (13) Å^3
Mr = 722.87	Z = 1
Triclinic, P1	F(000) = 384
a = 7.485 (6) Å	Dx = 1.298 Mg m^−3
b = 8.797 (7) Å	Mo Kα radiation, λ = 0.71073 Å
c = 14.171 (12) Å	µ = 0.09 mm^−1
α = 96.618 (13)°	T = 150 K
β = 93.306 (12)°	Block, colorless
γ = 91.826 (14)°	0.38 × 0.25 × 0.18 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3749 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.069
profile data from ω–scans	θmax = 27.6°, θmin = 1.5°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.841, Tmax = 1.000	k = −11→11
9807 measured reflections	l = −18→18
4241 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.163	w = 1/[σ^2(Fo^2) + (0.0909P)^2 + 0.1533P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
4241 reflections	Δρmax = 0.31 e Å^−3
253 parameters	Δρmin = −0.32 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
N3	0.05668 (15)	0.80443 (14)	0.58576 (8)	0.0276 (3)
H17	−0.449 (3)	1.117 (2)	0.5731 (14)	0.043 (5)*
O2	0.35824 (13)	0.63264 (11)	0.60615 (7)	0.0272 (2)
H2	0.2649	0.6826	0.6019	0.041*
O1	0.61536 (13)	0.25477 (12)	0.77565 (7)	0.0284 (2)
H1	0.5930	0.2009	0.8191	0.043*
N1	0.53876 (14)	0.08303 (12)	0.92632 (8)	0.0226 (2)
C5	0.16892 (18)	0.49318 (16)	0.70161 (10)	0.0260 (3)
H5	0.0680	0.5499	0.6854	0.031*
C2	0.46575 (17)	0.33039 (14)	0.75139 (9)	0.0211 (3)
C1	0.48523 (16)	0.44146 (14)	0.68883 (8)	0.0197 (3)
C16	−0.27043 (17)	0.94411 (15)	0.55200 (9)	0.0236 (3)
C6	0.33415 (17)	0.52338 (14)	0.66575 (9)	0.0212 (3)
C10	0.56826 (17)	0.14526 (14)	1.01728 (9)	0.0216 (3)
C3	0.29998 (18)	0.29797 (16)	0.78686 (10)	0.0258 (3)
H3	0.2884	0.2208	0.8281	0.031*
C9	0.47047 (17)	−0.06057 (15)	0.90820 (9)	0.0222 (3)
C4	0.15294 (18)	0.37928 (17)	0.76140 (10)	0.0277 (3)
H4	0.0399	0.3571	0.7850	0.033*
C11	0.6422 (2)	0.30721 (15)	1.03452 (11)	0.0314 (3)
H11A	0.6622	0.3450	0.9734	0.047*
H11B	0.7559	0.3108	1.0728	0.047*
H11C	0.5567	0.3717	1.0687	0.047*
C12	0.02464 (19)	0.94443 (17)	0.62782 (10)	0.0291 (3)
H12	0.1164	0.9970	0.6694	0.035*
C7	0.65978 (18)	0.47146 (16)	0.64559 (9)	0.0257 (3)
H7A	0.7565	0.4244	0.6802	0.039*
H7B	0.6846	0.5822	0.6497	0.039*
H7C	0.6521	0.4273	0.5787	0.039*
C8	0.4349 (2)	−0.12486 (17)	0.80571 (10)	0.0319 (3)
H8A	0.4819	−0.0525	0.7647	0.048*
H8B	0.3056	−0.1416	0.7916	0.048*
H8C	0.4941	−0.2224	0.7939	0.048*
C13	−0.13457 (19)	1.01654 (16)	0.61409 (10)	0.0279 (3)
H13	−0.1513	1.1150	0.6468	0.033*
C17	−0.43674 (18)	1.02289 (16)	0.53395 (10)	0.0267 (3)
C15	−0.2367 (2)	0.79864 (16)	0.50778 (11)	0.0303 (3)
H15	−0.3247	0.7438	0.4648	0.036*
C14	−0.0745 (2)	0.73541 (16)	0.52710 (11)	0.0308 (3)
H14	−0.0549	0.6359	0.4966	0.037*
N2	0.07637 (17)	0.18543 (14)	0.97256 (9)	0.0313 (3)
C22	0.03526 (17)	0.07416 (15)	1.02579 (9)	0.0242 (3)
C18	0.1399 (2)	0.32020 (17)	1.01808 (12)	0.0351 (4)
H18	0.1695	0.3997	0.9810	0.042*
C19	0.1647 (2)	0.34980 (17)	1.11594 (11)	0.0339 (3)
H19	0.2098	0.4470	1.1454	0.041*
C21	0.05751 (19)	0.09367 (17)	1.12457 (10)	0.0290 (3)
H21	0.0290	0.0121	1.1603	0.035*
C20	0.1218 (2)	0.23357 (18)	1.16980 (11)	0.0349 (3)
H20	0.1365	0.2501	1.2373	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N3	0.0296 (6)	0.0277 (6)	0.0277 (6)	0.0071 (5)	0.0003 (4)	0.0116 (5)
O2	0.0324 (5)	0.0275 (5)	0.0244 (5)	0.0094 (4)	0.0032 (4)	0.0108 (4)
O1	0.0277 (5)	0.0318 (5)	0.0293 (5)	0.0088 (4)	0.0035 (4)	0.0158 (4)
N1	0.0251 (5)	0.0195 (5)	0.0237 (6)	0.0021 (4)	−0.0014 (4)	0.0061 (4)
C5	0.0253 (6)	0.0266 (7)	0.0267 (7)	0.0074 (5)	0.0012 (5)	0.0044 (5)
C2	0.0248 (6)	0.0196 (6)	0.0190 (6)	0.0037 (5)	−0.0001 (4)	0.0027 (4)
C1	0.0240 (6)	0.0188 (6)	0.0159 (5)	0.0007 (4)	−0.0003 (4)	0.0011 (4)
C16	0.0273 (6)	0.0220 (6)	0.0225 (6)	0.0034 (5)	−0.0003 (5)	0.0064 (5)
C6	0.0279 (6)	0.0194 (6)	0.0162 (5)	0.0032 (5)	−0.0002 (4)	0.0013 (4)
C10	0.0230 (6)	0.0162 (5)	0.0257 (6)	0.0018 (4)	−0.0017 (4)	0.0037 (5)
C3	0.0291 (6)	0.0244 (6)	0.0255 (6)	0.0022 (5)	0.0043 (5)	0.0081 (5)
C9	0.0230 (6)	0.0199 (6)	0.0236 (6)	0.0029 (5)	−0.0020 (4)	0.0032 (5)
C4	0.0248 (6)	0.0301 (7)	0.0294 (7)	0.0028 (5)	0.0060 (5)	0.0061 (5)
C11	0.0366 (7)	0.0184 (6)	0.0388 (8)	−0.0043 (5)	−0.0013 (6)	0.0050 (5)
C12	0.0310 (7)	0.0309 (7)	0.0253 (7)	0.0029 (6)	−0.0051 (5)	0.0060 (5)
C7	0.0266 (6)	0.0290 (7)	0.0229 (6)	0.0014 (5)	0.0021 (5)	0.0077 (5)
C8	0.0394 (8)	0.0310 (7)	0.0240 (7)	0.0010 (6)	−0.0026 (6)	0.0000 (5)
C13	0.0339 (7)	0.0236 (6)	0.0254 (7)	0.0058 (5)	−0.0031 (5)	0.0014 (5)
C17	0.0294 (6)	0.0219 (6)	0.0284 (7)	0.0061 (5)	−0.0012 (5)	0.0018 (5)
C15	0.0329 (7)	0.0217 (7)	0.0350 (7)	0.0039 (5)	−0.0075 (6)	0.0020 (5)
C14	0.0367 (7)	0.0217 (6)	0.0344 (7)	0.0080 (5)	−0.0020 (6)	0.0051 (5)
N2	0.0380 (7)	0.0264 (6)	0.0295 (6)	−0.0052 (5)	0.0071 (5)	0.0019 (5)
C22	0.0239 (6)	0.0234 (7)	0.0253 (6)	0.0010 (5)	0.0049 (5)	0.0012 (5)
C18	0.0403 (8)	0.0262 (7)	0.0383 (8)	−0.0068 (6)	0.0099 (6)	0.0003 (6)
C19	0.0336 (7)	0.0267 (7)	0.0393 (8)	−0.0033 (6)	0.0069 (6)	−0.0066 (6)
C21	0.0344 (7)	0.0274 (7)	0.0250 (7)	0.0000 (5)	0.0043 (5)	0.0012 (5)
C20	0.0387 (8)	0.0342 (8)	0.0295 (7)	−0.0009 (6)	0.0046 (6)	−0.0061 (6)

Geometric parameters (Å, º)

N3—C14	1.333 (2)	C11—H11C	0.9800
N3—C12	1.340 (2)	C12—C13	1.382 (2)
O2—C6	1.3651 (17)	C12—H12	0.9500
O2—H2	0.8400	C7—H7A	0.9800
O1—C2	1.3676 (17)	C7—H7B	0.9800
O1—H1	0.8400	C7—H7C	0.9800
N1—C9	1.3386 (19)	C8—H8A	0.9800
N1—C10	1.344 (2)	C8—H8B	0.9800
C5—C4	1.391 (2)	C8—H8C	0.9800
C5—C6	1.393 (2)	C13—H13	0.9500
C5—H5	0.9500	C17—C17^ii	1.329 (3)
C2—C3	1.398 (2)	C17—H17	0.95 (2)
C2—C1	1.4027 (19)	C15—C14	1.378 (2)
C1—C6	1.4030 (19)	C15—H15	0.9500
C1—C7	1.503 (2)	C14—H14	0.9500
C16—C13	1.393 (2)	N2—C22	1.341 (2)
C16—C15	1.396 (2)	N2—C18	1.342 (2)
C16—C17	1.468 (2)	C22—C21	1.390 (2)
C10—C9^i	1.399 (2)	C22—C22^iii	1.486 (3)
C10—C11	1.500 (2)	C18—C19	1.382 (3)
C3—C4	1.385 (2)	C18—H18	0.9500
C3—H3	0.9500	C19—C20	1.385 (2)
C9—C10^i	1.399 (2)	C19—H19	0.9500
C9—C8	1.502 (2)	C21—C20	1.379 (2)
C4—H4	0.9500	C21—H21	0.9500
C11—H11A	0.9800	C20—H20	0.9500
C11—H11B	0.9800
C14—N3—C12	116.32 (12)	C1—C7—H7A	109.5
C6—O2—H2	109.5	C1—C7—H7B	109.5
C2—O1—H1	109.5	H7A—C7—H7B	109.5
C9—N1—C10	119.01 (11)	C1—C7—H7C	109.5
C4—C5—C6	119.44 (12)	H7A—C7—H7C	109.5
C4—C5—H5	120.3	H7B—C7—H7C	109.5
C6—C5—H5	120.3	C9—C8—H8A	109.5
O1—C2—C3	121.55 (12)	C9—C8—H8B	109.5
O1—C2—C1	117.16 (11)	H8A—C8—H8B	109.5
C3—C2—C1	121.28 (12)	C9—C8—H8C	109.5
C2—C1—C6	117.76 (12)	H8A—C8—H8C	109.5
C2—C1—C7	122.01 (11)	H8B—C8—H8C	109.5
C6—C1—C7	120.22 (12)	C12—C13—C16	119.68 (14)
C13—C16—C15	116.72 (13)	C12—C13—H13	120.2
C13—C16—C17	119.92 (13)	C16—C13—H13	120.2
C15—C16—C17	123.34 (12)	C17^ii—C17—C16	125.50 (17)
O2—C6—C5	122.29 (12)	C17^ii—C17—H17	118.9 (12)
O2—C6—C1	116.35 (12)	C16—C17—H17	115.5 (12)
C5—C6—C1	121.36 (13)	C14—C15—C16	119.28 (13)
N1—C10—C9^i	120.41 (13)	C14—C15—H15	120.4
N1—C10—C11	117.35 (12)	C16—C15—H15	120.4
C9^i—C10—C11	122.24 (13)	N3—C14—C15	124.38 (14)
C4—C3—C2	119.42 (13)	N3—C14—H14	117.8
C4—C3—H3	120.3	C15—C14—H14	117.8
C2—C3—H3	120.3	C22—N2—C18	117.58 (14)
N1—C9—C10^i	120.58 (13)	N2—C22—C21	122.58 (13)
N1—C9—C8	117.50 (12)	N2—C22—C22^iii	116.84 (16)
C10^i—C9—C8	121.91 (13)	C21—C22—C22^iii	120.58 (15)
C3—C4—C5	120.70 (13)	N2—C18—C19	123.62 (14)
C3—C4—H4	119.7	N2—C18—H18	118.2
C5—C4—H4	119.6	C19—C18—H18	118.2
C10—C11—H11A	109.5	C18—C19—C20	118.03 (14)
C10—C11—H11B	109.5	C18—C19—H19	121.0
H11A—C11—H11B	109.5	C20—C19—H19	121.0
C10—C11—H11C	109.5	C20—C21—C22	118.78 (14)
H11A—C11—H11C	109.5	C20—C21—H21	120.6
H11B—C11—H11C	109.5	C22—C21—H21	120.6
N3—C12—C13	123.60 (13)	C21—C20—C19	119.39 (15)
N3—C12—H12	118.2	C21—C20—H20	120.3
C13—C12—H12	118.2	C19—C20—H20	120.3

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

(MRE_TMP_DPE-I_22TP)

Crystal data

C42H44N4O4S2	V = 916.5 (11) Å^3
Mr = 732.93	Z = 1
Triclinic, P1	F(000) = 388
a = 7.492 (5) Å	Dx = 1.328 Mg m^−3
b = 9.069 (6) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.643 (10) Å	µ = 0.20 mm^−1
α = 98.069 (13)°	T = 150 K
β = 92.516 (6)°	Block, brown
γ = 91.428 (8)°	0.44 × 0.32 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3841 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.074
profile data from ω–scans	θmax = 27.6°, θmin = 1.5°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.834, Tmax = 1.000	k = −11→11
9797 measured reflections	l = −17→17
4205 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.146	w = 1/[σ^2(Fo^2) + (0.0691P)^2 + 0.4643P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
4205 reflections	Δρmax = 0.53 e Å^−3
244 parameters	Δρmin = −0.45 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C19	0.1411 (2)	0.8359 (2)	0.56403 (14)	0.0246 (4)
H19	0.1782	0.9297	0.6002	0.029*
H18	−0.450 (3)	0.373 (3)	0.9388 (17)	0.028 (6)*
S1	0.07132 (6)	0.68663 (5)	0.61752 (3)	0.02433 (15)
C22	0.0335 (2)	0.57649 (18)	0.50353 (12)	0.0186 (3)
C21	0.0751 (2)	0.65527 (18)	0.42590 (13)	0.0194 (3)
H21	0.0639	0.6154	0.3576	0.023*
C20	0.1373 (2)	0.8047 (2)	0.46349 (14)	0.0233 (4)
H20	0.1725	0.8750	0.4220	0.028*
O1	0.35570 (15)	0.85395 (13)	0.88697 (9)	0.0196 (3)
H1	0.2602	0.8068	0.8939	0.029*
O2	0.57797 (15)	1.23945 (13)	0.72288 (9)	0.0190 (3)
H2	0.5446	1.2944	0.6813	0.029*
C5	0.1152 (2)	1.12712 (18)	0.76131 (12)	0.0170 (3)
H5	−0.0037	1.1548	0.7471	0.020*
C7	0.4322 (2)	1.16643 (17)	0.75288 (11)	0.0150 (3)
C1	0.4668 (2)	1.04942 (17)	0.80735 (11)	0.0147 (3)
C3	0.3197 (2)	0.96938 (17)	0.83586 (11)	0.0150 (3)
C4	0.1446 (2)	1.00753 (18)	0.81259 (12)	0.0164 (3)
H4	0.0463	0.9518	0.8318	0.020*
C6	0.2585 (2)	1.20693 (18)	0.73049 (12)	0.0172 (3)
H6	0.2381	1.2880	0.6947	0.021*
C8	0.6560 (2)	1.01188 (19)	0.83424 (14)	0.0214 (4)
H8A	0.7218	0.9888	0.7737	0.032*
H8B	0.6547	0.9253	0.8699	0.032*
H8C	0.7147	1.0971	0.8766	0.032*
N1	0.51206 (18)	0.58232 (15)	0.42266 (10)	0.0166 (3)
C11	0.4648 (2)	0.43654 (18)	0.40511 (12)	0.0160 (3)
C10	0.5478 (2)	0.64675 (17)	0.51642 (12)	0.0156 (3)
C12	0.4284 (3)	0.3684 (2)	0.29895 (13)	0.0238 (4)
H12A	0.4491	0.4439	0.2555	0.036*
H12B	0.3040	0.3314	0.2895	0.036*
H12C	0.5084	0.2856	0.2826	0.036*
C9	0.6052 (2)	0.80863 (18)	0.53311 (14)	0.0211 (4)
H9A	0.7349	0.8177	0.5465	0.032*
H9B	0.5449	0.8599	0.5899	0.032*
H9C	0.5733	0.8539	0.4738	0.032*
N2	0.04982 (18)	0.69181 (15)	0.90918 (10)	0.0177 (3)
C15	−0.2731 (2)	0.55122 (17)	0.94930 (11)	0.0152 (3)
C18	−0.4381 (2)	0.47199 (18)	0.96998 (12)	0.0177 (3)
C16	−0.2294 (2)	0.69822 (17)	0.99034 (12)	0.0174 (3)
H16	−0.3087	0.7536	1.0327	0.021*
C13	0.0079 (2)	0.55041 (18)	0.86962 (12)	0.0176 (3)
H13	0.0901	0.4981	0.8276	0.021*
C14	−0.1497 (2)	0.47722 (18)	0.88730 (12)	0.0175 (3)
H14	−0.1739	0.3772	0.8574	0.021*
C17	−0.0696 (2)	0.76191 (18)	0.96849 (12)	0.0184 (3)
H17	−0.0420	0.8619	0.9973	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C19	0.0235 (8)	0.0227 (9)	0.0259 (9)	0.0012 (7)	0.0004 (7)	−0.0023 (7)
S1	0.0283 (3)	0.0248 (3)	0.0189 (2)	0.00097 (18)	0.00169 (17)	−0.00026 (17)
C22	0.0162 (7)	0.0215 (9)	0.0180 (8)	0.0055 (6)	0.0003 (6)	0.0016 (6)
C21	0.0184 (7)	0.0155 (7)	0.0251 (9)	0.0036 (6)	0.0019 (6)	0.0048 (6)
C20	0.0259 (8)	0.0207 (8)	0.0235 (9)	0.0018 (7)	0.0010 (7)	0.0037 (7)
O1	0.0182 (5)	0.0181 (6)	0.0252 (6)	−0.0007 (4)	0.0023 (5)	0.0119 (5)
O2	0.0191 (6)	0.0199 (6)	0.0201 (6)	−0.0026 (4)	0.0017 (4)	0.0103 (5)
C5	0.0171 (7)	0.0181 (8)	0.0162 (7)	0.0041 (6)	0.0018 (6)	0.0025 (6)
C7	0.0184 (7)	0.0142 (7)	0.0123 (7)	−0.0010 (6)	0.0028 (6)	0.0008 (6)
C1	0.0165 (7)	0.0131 (7)	0.0144 (7)	0.0012 (5)	0.0016 (5)	0.0014 (6)
C3	0.0195 (7)	0.0124 (7)	0.0133 (7)	0.0015 (6)	0.0020 (6)	0.0020 (5)
C4	0.0173 (7)	0.0166 (7)	0.0156 (7)	−0.0004 (6)	0.0040 (6)	0.0023 (6)
C6	0.0220 (8)	0.0146 (7)	0.0158 (7)	0.0029 (6)	0.0023 (6)	0.0037 (6)
C8	0.0170 (8)	0.0210 (8)	0.0279 (9)	−0.0002 (6)	−0.0002 (6)	0.0098 (7)
N1	0.0182 (6)	0.0146 (6)	0.0183 (7)	0.0023 (5)	0.0019 (5)	0.0055 (5)
C11	0.0164 (7)	0.0143 (7)	0.0174 (8)	0.0033 (6)	0.0018 (6)	0.0023 (6)
C10	0.0155 (7)	0.0138 (7)	0.0179 (8)	0.0027 (5)	0.0011 (6)	0.0033 (6)
C12	0.0325 (9)	0.0218 (8)	0.0166 (8)	0.0000 (7)	−0.0008 (7)	0.0024 (7)
C9	0.0242 (8)	0.0136 (8)	0.0258 (9)	0.0001 (6)	−0.0003 (7)	0.0042 (6)
N2	0.0196 (6)	0.0174 (7)	0.0174 (7)	−0.0002 (5)	0.0030 (5)	0.0058 (5)
C15	0.0172 (7)	0.0158 (7)	0.0130 (7)	−0.0001 (6)	0.0002 (6)	0.0036 (6)
C18	0.0199 (8)	0.0147 (7)	0.0179 (8)	−0.0020 (6)	0.0005 (6)	0.0013 (6)
C16	0.0218 (8)	0.0138 (7)	0.0170 (8)	0.0023 (6)	0.0042 (6)	0.0019 (6)
C13	0.0198 (7)	0.0187 (8)	0.0147 (7)	0.0024 (6)	0.0028 (6)	0.0032 (6)
C14	0.0211 (8)	0.0148 (7)	0.0161 (7)	0.0005 (6)	0.0008 (6)	0.0010 (6)
C17	0.0230 (8)	0.0138 (7)	0.0190 (8)	−0.0009 (6)	0.0032 (6)	0.0037 (6)

Geometric parameters (Å, º)

C19—C20	1.360 (3)	N1—C10	1.342 (2)
C19—S1	1.707 (2)	N1—C11	1.346 (2)
C19—H19	0.9500	C11—C10^ii	1.399 (2)
S1—C22	1.734 (2)	C11—C12	1.503 (2)
C22—C21	1.400 (2)	C10—C11^ii	1.399 (2)
C22—C22^i	1.452 (3)	C10—C9	1.503 (2)
C21—C20	1.438 (2)	C12—H12A	0.9800
C21—H21	0.9500	C12—H12B	0.9800
C20—H20	0.9500	C12—H12C	0.9800
O1—C3	1.363 (2)	C9—H9A	0.9800
O1—H1	0.8400	C9—H9B	0.9800
O2—C7	1.3703 (19)	C9—H9C	0.9800
O2—H2	0.8400	N2—C13	1.343 (2)
C5—C4	1.388 (2)	N2—C17	1.344 (2)
C5—C6	1.393 (2)	C15—C16	1.397 (2)
C5—H5	0.9500	C15—C14	1.400 (2)
C7—C6	1.393 (2)	C15—C18	1.472 (2)
C7—C1	1.401 (2)	C18—C18^iii	1.328 (3)
C1—C3	1.404 (2)	C18—H18	0.94 (2)
C1—C8	1.508 (2)	C16—C17	1.379 (2)
C3—C4	1.399 (2)	C16—H16	0.9500
C4—H4	0.9500	C13—C14	1.387 (2)
C6—H6	0.9500	C13—H13	0.9500
C8—H8A	0.9800	C14—H14	0.9500
C8—H8B	0.9800	C17—H17	0.9500
C8—H8C	0.9800
C20—C19—S1	112.00 (14)	C10—N1—C11	119.14 (14)
C20—C19—H19	124.0	N1—C11—C10^ii	120.48 (15)
S1—C19—H19	124.0	N1—C11—C12	117.40 (14)
C19—S1—C22	92.39 (10)	C10^ii—C11—C12	122.13 (15)
C21—C22—C22^i	127.7 (2)	N1—C10—C11^ii	120.38 (15)
C21—C22—S1	111.08 (13)	N1—C10—C9	117.74 (14)
C22^i—C22—S1	121.18 (17)	C11^ii—C10—C9	121.86 (15)
C22—C21—C20	110.83 (16)	C11—C12—H12A	109.5
C22—C21—H21	124.6	C11—C12—H12B	109.5
C20—C21—H21	124.6	H12A—C12—H12B	109.5
C19—C20—C21	113.69 (16)	C11—C12—H12C	109.5
C19—C20—H20	123.2	H12A—C12—H12C	109.5
C21—C20—H20	123.2	H12B—C12—H12C	109.5
C3—O1—H1	109.5	C10—C9—H9A	109.5
C7—O2—H2	109.5	C10—C9—H9B	109.5
C4—C5—C6	120.51 (15)	H9A—C9—H9B	109.5
C4—C5—H5	119.7	C10—C9—H9C	109.5
C6—C5—H5	119.7	H9A—C9—H9C	109.5
O2—C7—C6	121.59 (14)	H9B—C9—H9C	109.5
O2—C7—C1	116.61 (14)	C13—N2—C17	116.70 (14)
C6—C7—C1	121.80 (14)	C16—C15—C14	117.08 (15)
C7—C1—C3	117.69 (14)	C16—C15—C18	123.28 (15)
C7—C1—C8	120.78 (14)	C14—C15—C18	119.63 (15)
C3—C1—C8	121.54 (14)	C18^iii—C18—C15	125.3 (2)
O1—C3—C4	122.01 (14)	C18^iii—C18—H18	119.8 (14)
O1—C3—C1	116.94 (14)	C15—C18—H18	114.8 (14)
C4—C3—C1	121.05 (14)	C17—C16—C15	119.08 (15)
C5—C4—C3	119.73 (14)	C17—C16—H16	120.5
C5—C4—H4	120.1	C15—C16—H16	120.5
C3—C4—H4	120.1	N2—C13—C14	123.07 (15)
C5—C6—C7	119.18 (15)	N2—C13—H13	118.5
C5—C6—H6	120.4	C14—C13—H13	118.5
C7—C6—H6	120.4	C13—C14—C15	119.78 (15)
C1—C8—H8A	109.5	C13—C14—H14	120.1
C1—C8—H8B	109.5	C15—C14—H14	120.1
H8A—C8—H8B	109.5	N2—C17—C16	124.29 (16)
C1—C8—H8C	109.5	N2—C17—H17	117.9
H8A—C8—H8C	109.5	C16—C17—H17	117.9
H8B—C8—H8C	109.5

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

(Form_I_MRE_TMP_DPE-I_ACR)

Crystal data

C90H96N10O8	V = 1919.9 (5) Å^3
Mr = 1445.76	Z = 1
Triclinic, P1	F(000) = 770
a = 7.3795 (10) Å	Dx = 1.250 Mg m^−3
b = 8.8871 (13) Å	Mo Kα radiation, λ = 0.71073 Å
c = 29.533 (5) Å	µ = 0.08 mm^−1
α = 89.495 (17)°	T = 150 K
β = 84.054 (16)°	Block, green
γ = 85.281 (10)°	0.35 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	6196 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.091
profile data from ω–scans	θmax = 27.6°, θmin = 0.7°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.693, Tmax = 1.000	k = −11→11
19146 measured reflections	l = −38→38
8793 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.069	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.229	w = 1/[σ^2(Fo^2) + (0.1126P)^2 + 0.0124P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.040
8793 reflections	Δρmax = 0.32 e Å^−3
503 parameters	Δρmin = −0.32 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
H32	1.436 (4)	2.101 (3)	0.0363 (10)	0.044 (7)*
C1	0.4745 (3)	0.4820 (2)	0.40922 (7)	0.0271 (4)
C2	0.3547 (3)	0.3747 (2)	0.42537 (7)	0.0273 (4)
C3	0.1990 (3)	0.3512 (2)	0.40442 (8)	0.0323 (5)
H3	0.1187	0.2786	0.4161	0.039*
C4	0.1632 (3)	0.4352 (3)	0.36626 (8)	0.0369 (5)
H4	0.0570	0.4202	0.3518	0.044*
C5	0.2798 (3)	0.5410 (3)	0.34879 (8)	0.0350 (5)
H5	0.2542	0.5976	0.3224	0.042*
C6	0.4344 (3)	0.5632 (2)	0.37019 (7)	0.0300 (5)
C7	0.6408 (3)	0.5085 (3)	0.43257 (8)	0.0365 (5)
H7A	0.6999	0.5943	0.4183	0.055*
H7B	0.7265	0.4181	0.4298	0.055*
H7C	0.6042	0.5306	0.4648	0.055*
C8	0.3537 (3)	−0.1027 (3)	0.45711 (9)	0.0408 (6)
H8A	0.4257	−0.0157	0.4507	0.061*
H8B	0.3419	−0.1549	0.4286	0.061*
H8C	0.4152	−0.1722	0.4777	0.061*
C9	0.1669 (3)	−0.0495 (2)	0.47919 (7)	0.0295 (5)
C10	−0.0253 (3)	0.1461 (2)	0.51307 (7)	0.0308 (5)
C11	−0.0512 (4)	0.3085 (3)	0.52744 (9)	0.0417 (6)
H11A	0.0605	0.3580	0.5180	0.063*
H11B	−0.0774	0.3144	0.5606	0.063*
H11C	−0.1536	0.3592	0.5131	0.063*
C12	0.5047 (3)	0.7658 (2)	0.23437 (8)	0.0321 (5)
C13	0.4898 (3)	0.8621 (3)	0.19668 (8)	0.0338 (5)
C14	0.3745 (3)	1.0583 (2)	0.24526 (8)	0.0315 (5)
C15	0.3860 (3)	0.9620 (3)	0.28265 (8)	0.0319 (5)
C16	0.5763 (4)	0.6036 (3)	0.22865 (10)	0.0466 (6)
H16A	0.5832	0.5568	0.2587	0.070*
H16B	0.6985	0.5978	0.2119	0.070*
H16C	0.4941	0.5503	0.2116	0.070*
C17	0.5484 (4)	0.8089 (3)	0.14901 (9)	0.0492 (7)
H17A	0.5093	0.8864	0.1275	0.074*
H17B	0.4923	0.7153	0.1436	0.074*
H17C	0.6818	0.7902	0.1448	0.074*
C18	0.3067 (4)	1.2213 (3)	0.24988 (10)	0.0464 (6)
H18A	0.3397	1.2740	0.2213	0.070*
H18B	0.3625	1.2667	0.2746	0.070*
H18C	0.1735	1.2298	0.2568	0.070*
C19	0.3258 (4)	1.0144 (3)	0.33031 (9)	0.0459 (6)
H19A	0.3297	0.9278	0.3511	0.069*
H19B	0.2006	1.0618	0.3319	0.069*
H19C	0.4076	1.0879	0.3392	0.069*
C20	0.5166 (3)	1.4038 (2)	0.09189 (7)	0.0261 (4)
C21	0.5319 (3)	1.2832 (2)	0.12216 (7)	0.0302 (5)
C22	0.6932 (3)	1.2466 (3)	0.14198 (8)	0.0354 (5)
H22	0.7021	1.1639	0.1625	0.042*
C23	0.8411 (3)	1.3325 (3)	0.13138 (9)	0.0380 (5)
H23	0.9515	1.3077	0.1447	0.046*
C24	0.8299 (3)	1.4531 (3)	0.10181 (8)	0.0346 (5)
H24	0.9315	1.5114	0.0949	0.042*
C25	0.6676 (3)	1.4887 (2)	0.08220 (7)	0.0275 (4)
C26	0.3444 (3)	1.4416 (3)	0.06954 (8)	0.0331 (5)
H26A	0.3105	1.5504	0.0719	0.050*
H26B	0.2456	1.3865	0.0848	0.050*
H26C	0.3651	1.4124	0.0374	0.050*
C27	0.9595 (3)	1.9179 (3)	0.06054 (8)	0.0346 (5)
H27	0.8584	1.9630	0.0796	0.042*
C28	1.1161 (3)	1.9948 (3)	0.05372 (8)	0.0332 (5)
H28	1.1217	2.0885	0.0685	0.040*
C29	1.2666 (3)	1.9332 (2)	0.02471 (7)	0.0293 (5)
C30	1.2487 (3)	1.7946 (2)	0.00539 (8)	0.0356 (5)
H30	1.3469	1.7470	−0.0141	0.043*
C31	1.0877 (3)	1.7255 (3)	0.01445 (8)	0.0364 (5)
H31	1.0791	1.6308	0.0005	0.044*
C32	1.4314 (3)	2.0162 (2)	0.01617 (8)	0.0322 (5)
N1	0.1382 (3)	0.09501 (19)	0.49244 (6)	0.0308 (4)
N2	0.4531 (3)	0.8185 (2)	0.27655 (7)	0.0332 (4)
N3	0.4259 (3)	1.0054 (2)	0.20279 (6)	0.0324 (4)
N4	0.9426 (3)	1.7840 (2)	0.04185 (7)	0.0345 (4)
O1	0.3996 (2)	0.29454 (18)	0.46281 (5)	0.0369 (4)
H1	0.3151	0.2401	0.4717	0.055*
O2	0.5559 (2)	0.6635 (2)	0.35396 (6)	0.0419 (4)
H2	0.5208	0.7054	0.3304	0.063*
O3	0.3813 (2)	1.20263 (19)	0.13095 (6)	0.0396 (4)
H3A	0.4021	1.1355	0.1504	0.059*
O4	0.6478 (2)	1.60550 (18)	0.05248 (5)	0.0354 (4)
H4A	0.7391	1.6564	0.0516	0.053*
C33	0.8657 (3)	−0.0690 (3)	0.31393 (10)	0.0453 (6)
C34	0.8102 (4)	−0.0280 (4)	0.36042 (12)	0.0637 (9)
H34	0.8117	−0.1031	0.3835	0.076*
C35	0.7548 (5)	0.1192 (5)	0.37183 (14)	0.0753 (12)
H35	0.7199	0.1452	0.4028	0.090*
C36	0.7491 (4)	0.2313 (4)	0.33841 (15)	0.0746 (11)
H36	0.7087	0.3322	0.3471	0.089*
C37	0.7996 (4)	0.1993 (3)	0.29411 (13)	0.0608 (9)
H37	0.7950	0.2774	0.2720	0.073*
C38	0.8605 (3)	0.0473 (3)	0.28027 (10)	0.0448 (6)
C40	0.9753 (3)	−0.1190 (3)	0.22282 (9)	0.0398 (6)
C41	1.0334 (4)	−0.1446 (4)	0.17583 (10)	0.0528 (7)
H41	1.0268	−0.0634	0.1548	0.063*
C42	1.0984 (4)	−0.2853 (4)	0.16110 (11)	0.0591 (8)
H42	1.1365	−0.3013	0.1297	0.071*
C43	1.1101 (4)	−0.4074 (3)	0.19155 (12)	0.0585 (8)
H43	1.1564	−0.5046	0.1806	0.070*
C44	1.0559 (4)	−0.3871 (3)	0.23630 (11)	0.0504 (7)
H44	1.0647	−0.4707	0.2564	0.060*
C45	0.9855 (3)	−0.2423 (3)	0.25405 (9)	0.0408 (6)
C46	0.9270 (3)	−0.2130 (3)	0.29950 (9)	0.0430 (6)
H46	0.9293	−0.2933	0.3210	0.052*
N5	0.9131 (3)	0.0225 (2)	0.23576 (8)	0.0460 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0279 (11)	0.0278 (11)	0.0252 (10)	0.0011 (8)	−0.0036 (8)	−0.0013 (8)
C2	0.0344 (12)	0.0237 (10)	0.0231 (10)	0.0011 (8)	−0.0029 (8)	−0.0018 (7)
C3	0.0328 (12)	0.0312 (11)	0.0337 (12)	−0.0072 (9)	−0.0035 (9)	−0.0026 (8)
C4	0.0355 (13)	0.0419 (13)	0.0358 (13)	−0.0079 (10)	−0.0116 (10)	0.0013 (9)
C5	0.0375 (13)	0.0382 (13)	0.0308 (12)	−0.0028 (9)	−0.0112 (9)	0.0067 (9)
C6	0.0322 (12)	0.0289 (11)	0.0284 (11)	−0.0021 (8)	−0.0017 (9)	0.0034 (8)
C7	0.0361 (13)	0.0426 (13)	0.0321 (12)	−0.0055 (10)	−0.0085 (10)	0.0018 (9)
C8	0.0410 (14)	0.0387 (13)	0.0410 (14)	0.0017 (10)	0.0009 (10)	−0.0028 (10)
C9	0.0396 (13)	0.0268 (11)	0.0218 (10)	−0.0002 (9)	−0.0039 (8)	0.0001 (8)
C10	0.0409 (13)	0.0242 (10)	0.0276 (11)	−0.0014 (9)	−0.0069 (9)	0.0016 (8)
C11	0.0497 (16)	0.0257 (12)	0.0494 (15)	−0.0001 (10)	−0.0051 (12)	−0.0061 (10)
C12	0.0265 (12)	0.0288 (11)	0.0405 (13)	−0.0012 (8)	−0.0026 (9)	0.0031 (9)
C13	0.0313 (12)	0.0338 (12)	0.0355 (12)	−0.0023 (9)	0.0005 (9)	0.0005 (9)
C14	0.0304 (12)	0.0300 (11)	0.0347 (12)	−0.0038 (8)	−0.0055 (9)	0.0017 (8)
C15	0.0300 (12)	0.0347 (12)	0.0317 (12)	−0.0045 (9)	−0.0057 (9)	0.0016 (9)
C16	0.0415 (15)	0.0307 (13)	0.0663 (19)	0.0052 (10)	−0.0053 (12)	0.0025 (11)
C17	0.0550 (18)	0.0495 (16)	0.0402 (15)	−0.0015 (12)	0.0065 (12)	−0.0043 (11)
C18	0.0592 (18)	0.0300 (13)	0.0493 (16)	0.0022 (11)	−0.0067 (13)	−0.0014 (10)
C19	0.0545 (17)	0.0521 (16)	0.0315 (13)	−0.0063 (12)	−0.0048 (11)	−0.0031 (10)
C20	0.0280 (11)	0.0280 (10)	0.0221 (10)	−0.0010 (8)	−0.0024 (8)	−0.0008 (7)
C21	0.0328 (12)	0.0310 (11)	0.0275 (11)	−0.0047 (9)	−0.0053 (9)	0.0008 (8)
C22	0.0390 (13)	0.0301 (11)	0.0382 (13)	−0.0008 (9)	−0.0121 (10)	0.0065 (9)
C23	0.0315 (13)	0.0393 (13)	0.0447 (14)	−0.0005 (9)	−0.0133 (10)	0.0027 (10)
C24	0.0309 (12)	0.0372 (12)	0.0372 (13)	−0.0077 (9)	−0.0072 (9)	0.0014 (9)
C25	0.0300 (11)	0.0283 (11)	0.0241 (10)	−0.0029 (8)	−0.0012 (8)	−0.0012 (8)
C26	0.0288 (12)	0.0374 (12)	0.0329 (12)	−0.0002 (9)	−0.0045 (9)	0.0036 (9)
C27	0.0333 (13)	0.0391 (13)	0.0304 (12)	−0.0032 (9)	0.0018 (9)	0.0023 (9)
C28	0.0365 (13)	0.0338 (12)	0.0283 (11)	−0.0039 (9)	0.0012 (9)	−0.0019 (8)
C29	0.0307 (12)	0.0276 (11)	0.0295 (11)	−0.0038 (8)	−0.0024 (9)	0.0045 (8)
C30	0.0345 (13)	0.0282 (11)	0.0424 (13)	−0.0027 (9)	0.0041 (10)	−0.0014 (9)
C31	0.0381 (14)	0.0280 (11)	0.0430 (14)	−0.0056 (9)	−0.0019 (10)	0.0022 (9)
C32	0.0348 (13)	0.0287 (11)	0.0332 (12)	−0.0053 (9)	−0.0013 (9)	−0.0018 (9)
N1	0.0361 (11)	0.0276 (9)	0.0284 (10)	−0.0018 (8)	−0.0022 (8)	0.0033 (7)
N2	0.0337 (11)	0.0341 (10)	0.0330 (10)	−0.0058 (8)	−0.0081 (8)	0.0069 (8)
N3	0.0353 (11)	0.0310 (10)	0.0308 (10)	−0.0035 (8)	−0.0026 (8)	0.0040 (7)
N4	0.0334 (11)	0.0354 (11)	0.0353 (11)	−0.0080 (8)	−0.0032 (8)	0.0099 (8)
O1	0.0446 (10)	0.0380 (9)	0.0302 (9)	−0.0102 (7)	−0.0092 (7)	0.0094 (6)
O2	0.0390 (10)	0.0467 (10)	0.0430 (10)	−0.0144 (8)	−0.0110 (7)	0.0175 (8)
O3	0.0367 (10)	0.0426 (10)	0.0422 (10)	−0.0134 (7)	−0.0106 (7)	0.0164 (7)
O4	0.0376 (10)	0.0358 (9)	0.0347 (9)	−0.0107 (7)	−0.0075 (7)	0.0097 (6)
C33	0.0281 (13)	0.0569 (16)	0.0524 (16)	−0.0084 (11)	−0.0061 (11)	−0.0138 (12)
C34	0.0411 (17)	0.092 (3)	0.057 (2)	−0.0158 (16)	0.0071 (14)	−0.0161 (16)
C35	0.0452 (19)	0.094 (3)	0.084 (3)	−0.0119 (18)	0.0151 (17)	−0.047 (2)
C36	0.0447 (19)	0.068 (2)	0.108 (3)	−0.0047 (16)	0.0105 (18)	−0.047 (2)
C37	0.0360 (16)	0.0483 (17)	0.097 (3)	0.0043 (12)	−0.0039 (15)	−0.0261 (16)
C38	0.0291 (13)	0.0433 (15)	0.0628 (18)	−0.0015 (10)	−0.0084 (11)	−0.0162 (12)
C40	0.0366 (14)	0.0386 (13)	0.0462 (14)	0.0035 (10)	−0.0178 (11)	−0.0099 (10)
C41	0.0534 (18)	0.0621 (18)	0.0448 (16)	0.0027 (13)	−0.0191 (13)	−0.0120 (13)
C42	0.0546 (19)	0.074 (2)	0.0497 (17)	0.0044 (15)	−0.0175 (14)	−0.0267 (15)
C43	0.0482 (17)	0.0545 (18)	0.075 (2)	0.0103 (13)	−0.0263 (15)	−0.0335 (15)
C44	0.0451 (16)	0.0400 (14)	0.069 (2)	0.0054 (11)	−0.0262 (13)	−0.0109 (12)
C45	0.0342 (13)	0.0371 (13)	0.0538 (16)	0.0008 (10)	−0.0188 (11)	−0.0083 (11)
C46	0.0328 (13)	0.0488 (15)	0.0497 (16)	−0.0053 (10)	−0.0134 (11)	0.0016 (11)
N5	0.0408 (13)	0.0415 (12)	0.0569 (15)	0.0027 (9)	−0.0144 (10)	−0.0059 (10)

Geometric parameters (Å, º)

C1—C6	1.400 (3)	C21—C22	1.394 (3)
C1—C2	1.400 (3)	C22—C23	1.390 (3)
C1—C7	1.504 (3)	C22—H22	0.9500
C2—O1	1.365 (2)	C23—C24	1.379 (3)
C2—C3	1.391 (3)	C23—H23	0.9500
C3—C4	1.383 (3)	C24—C25	1.396 (3)
C3—H3	0.9500	C24—H24	0.9500
C4—C5	1.387 (3)	C25—O4	1.362 (2)
C4—H4	0.9500	C26—H26A	0.9800
C5—C6	1.389 (3)	C26—H26B	0.9800
C5—H5	0.9500	C26—H26C	0.9800
C6—O2	1.365 (3)	C27—N4	1.337 (3)
C7—H7A	0.9800	C27—C28	1.386 (3)
C7—H7B	0.9800	C27—H27	0.9500
C7—H7C	0.9800	C28—C29	1.407 (3)
C8—C9	1.504 (3)	C28—H28	0.9500
C8—H8A	0.9800	C29—C30	1.384 (3)
C8—H8B	0.9800	C29—C32	1.472 (3)
C8—H8C	0.9800	C30—C31	1.383 (3)
C9—N1	1.339 (3)	C30—H30	0.9500
C9—C10^i	1.406 (3)	C31—N4	1.345 (3)
C10—N1	1.340 (3)	C31—H31	0.9500
C10—C9^i	1.406 (3)	C32—C32^ii	1.333 (4)
C10—C11	1.499 (3)	C32—H32	0.97 (3)
C11—H11A	0.9800	O1—H1	0.8400
C11—H11B	0.9800	O2—H2	0.8400
C11—H11C	0.9800	O3—H3A	0.8400
C12—N2	1.342 (3)	O4—H4A	0.8400
C12—C13	1.406 (3)	C33—C46	1.379 (4)
C12—C16	1.498 (3)	C33—C38	1.429 (4)
C13—N3	1.328 (3)	C33—C34	1.433 (4)
C13—C17	1.498 (3)	C34—C35	1.372 (5)
C14—N3	1.349 (3)	C34—H34	0.9500
C14—C15	1.397 (3)	C35—C36	1.397 (6)
C14—C18	1.495 (3)	C35—H35	0.9500
C15—N2	1.336 (3)	C36—C37	1.349 (5)
C15—C19	1.498 (3)	C36—H36	0.9500
C16—H16A	0.9800	C37—C38	1.437 (4)
C16—H16B	0.9800	C37—H37	0.9500
C16—H16C	0.9800	C38—N5	1.346 (4)
C17—H17A	0.9800	C40—N5	1.347 (3)
C17—H17B	0.9800	C40—C41	1.424 (4)
C17—H17C	0.9800	C40—C45	1.429 (4)
C18—H18A	0.9800	C41—C42	1.360 (4)
C18—H18B	0.9800	C41—H41	0.9500
C18—H18C	0.9800	C42—C43	1.406 (5)
C19—H19A	0.9800	C42—H42	0.9500
C19—H19B	0.9800	C43—C44	1.350 (4)
C19—H19C	0.9800	C43—H43	0.9500
C20—C21	1.395 (3)	C44—C45	1.430 (4)
C20—C25	1.400 (3)	C44—H44	0.9500
C20—C26	1.504 (3)	C45—C46	1.387 (4)
C21—O3	1.373 (3)	C46—H46	0.9500
C6—C1—C2	117.41 (19)	C23—C22—C21	119.2 (2)
C6—C1—C7	121.05 (19)	C23—C22—H22	120.4
C2—C1—C7	121.54 (19)	C21—C22—H22	120.4
O1—C2—C3	121.96 (19)	C24—C23—C22	121.0 (2)
O1—C2—C1	116.12 (19)	C24—C23—H23	119.5
C3—C2—C1	121.92 (19)	C22—C23—H23	119.5
C4—C3—C2	118.8 (2)	C23—C24—C25	119.3 (2)
C4—C3—H3	120.6	C23—C24—H24	120.4
C2—C3—H3	120.6	C25—C24—H24	120.4
C3—C4—C5	121.1 (2)	O4—C25—C24	122.32 (19)
C3—C4—H4	119.5	O4—C25—C20	116.52 (19)
C5—C4—H4	119.5	C24—C25—C20	121.16 (19)
C4—C5—C6	119.3 (2)	C20—C26—H26A	109.5
C4—C5—H5	120.3	C20—C26—H26B	109.5
C6—C5—H5	120.3	H26A—C26—H26B	109.5
O2—C6—C5	121.87 (19)	C20—C26—H26C	109.5
O2—C6—C1	116.69 (19)	H26A—C26—H26C	109.5
C5—C6—C1	121.4 (2)	H26B—C26—H26C	109.5
C1—C7—H7A	109.5	N4—C27—C28	123.8 (2)
C1—C7—H7B	109.5	N4—C27—H27	118.1
H7A—C7—H7B	109.5	C28—C27—H27	118.1
C1—C7—H7C	109.5	C27—C28—C29	119.6 (2)
H7A—C7—H7C	109.5	C27—C28—H28	120.2
H7B—C7—H7C	109.5	C29—C28—H28	120.2
C9—C8—H8A	109.5	C30—C29—C28	116.5 (2)
C9—C8—H8B	109.5	C30—C29—C32	123.6 (2)
H8A—C8—H8B	109.5	C28—C29—C32	120.0 (2)
C9—C8—H8C	109.5	C31—C30—C29	119.9 (2)
H8A—C8—H8C	109.5	C31—C30—H30	120.0
H8B—C8—H8C	109.5	C29—C30—H30	120.0
N1—C9—C10^i	119.8 (2)	N4—C31—C30	124.0 (2)
N1—C9—C8	117.8 (2)	N4—C31—H31	118.0
C10^i—C9—C8	122.4 (2)	C30—C31—H31	118.0
N1—C10—C9^i	120.55 (19)	C32^ii—C32—C29	125.6 (3)
N1—C10—C11	117.8 (2)	C32^ii—C32—H32	119.8 (16)
C9^i—C10—C11	121.6 (2)	C29—C32—H32	114.7 (16)
C10—C11—H11A	109.5	C9—N1—C10	119.64 (19)
C10—C11—H11B	109.5	C15—N2—C12	119.99 (18)
H11A—C11—H11B	109.5	C13—N3—C14	119.89 (18)
C10—C11—H11C	109.5	C27—N4—C31	116.15 (19)
H11A—C11—H11C	109.5	C2—O1—H1	109.5
H11B—C11—H11C	109.5	C6—O2—H2	109.5
N2—C12—C13	119.9 (2)	C21—O3—H3A	109.5
N2—C12—C16	118.7 (2)	C25—O4—H4A	109.5
C13—C12—C16	121.5 (2)	C46—C33—C38	117.6 (3)
N3—C13—C12	120.1 (2)	C46—C33—C34	124.4 (3)
N3—C13—C17	118.1 (2)	C38—C33—C34	118.1 (3)
C12—C13—C17	121.8 (2)	C35—C34—C33	120.4 (3)
N3—C14—C15	120.0 (2)	C35—C34—H34	119.8
N3—C14—C18	117.3 (2)	C33—C34—H34	119.8
C15—C14—C18	122.7 (2)	C34—C35—C36	120.8 (3)
N2—C15—C14	120.1 (2)	C34—C35—H35	119.6
N2—C15—C19	117.9 (2)	C36—C35—H35	119.6
C14—C15—C19	122.0 (2)	C37—C36—C35	121.4 (3)
C12—C16—H16A	109.5	C37—C36—H36	119.3
C12—C16—H16B	109.5	C35—C36—H36	119.3
H16A—C16—H16B	109.5	C36—C37—C38	120.2 (4)
C12—C16—H16C	109.5	C36—C37—H37	119.9
H16A—C16—H16C	109.5	C38—C37—H37	119.9
H16B—C16—H16C	109.5	N5—C38—C33	123.2 (2)
C13—C17—H17A	109.5	N5—C38—C37	117.6 (3)
C13—C17—H17B	109.5	C33—C38—C37	119.2 (3)
H17A—C17—H17B	109.5	N5—C40—C41	117.8 (2)
C13—C17—H17C	109.5	N5—C40—C45	122.9 (2)
H17A—C17—H17C	109.5	C41—C40—C45	119.3 (2)
H17B—C17—H17C	109.5	C42—C41—C40	120.0 (3)
C14—C18—H18A	109.5	C42—C41—H41	120.0
C14—C18—H18B	109.5	C40—C41—H41	120.0
H18A—C18—H18B	109.5	C41—C42—C43	121.2 (3)
C14—C18—H18C	109.5	C41—C42—H42	119.4
H18A—C18—H18C	109.5	C43—C42—H42	119.4
H18B—C18—H18C	109.5	C44—C43—C42	120.3 (3)
C15—C19—H19A	109.5	C44—C43—H43	119.8
C15—C19—H19B	109.5	C42—C43—H43	119.8
H19A—C19—H19B	109.5	C43—C44—C45	121.4 (3)
C15—C19—H19C	109.5	C43—C44—H44	119.3
H19A—C19—H19C	109.5	C45—C44—H44	119.3
H19B—C19—H19C	109.5	C46—C45—C40	117.6 (2)
C21—C20—C25	118.14 (19)	C46—C45—C44	124.6 (3)
C21—C20—C26	121.45 (19)	C40—C45—C44	117.8 (3)
C25—C20—C26	120.40 (18)	C33—C46—C45	120.8 (2)
O3—C21—C22	122.15 (19)	C33—C46—H46	119.6
O3—C21—C20	116.61 (19)	C45—C46—H46	119.6
C22—C21—C20	121.2 (2)	C38—N5—C40	117.9 (2)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+3, −y+4, −z.

(Form_II_MRE_TMP_DPE-I_ACR)

Crystal data

C75H73N8O6	V = 1524 (4) Å^3
Mr = 1182.41	Z = 1
Triclinic, P1	F(000) = 627
a = 7.478 (12) Å	Dx = 1.288 Mg m^−3
b = 8.739 (14) Å	Mo Kα radiation, λ = 0.71073 Å
c = 23.37 (3) Å	µ = 0.08 mm^−1
α = 92.36 (3)°	T = 150 K
β = 90.29 (3)°	Block, pale yellow
γ = 93.131 (19)°	0.30 × 0.30 × 0.12 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	4024 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.114
profile data from ω–scans	θmax = 27.9°, θmin = 0.9°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.532, Tmax = 1.000	k = −11→11
13754 measured reflections	l = −30→30
7022 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)] = 0.092	w = 1/[σ^2(Fo^2) + (0.1605P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.300	(Δ/σ)max = 0.006
S = 1.01	Δρmax = 0.55 e Å^−3
7022 reflections	Δρmin = −0.41 e Å^−3
418 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.058 (9)

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.5502 (3)	0.5810 (3)	0.38476 (9)	0.0318 (5)
C2	0.6963 (4)	0.4975 (3)	0.39779 (10)	0.0343 (6)
C3	0.8632 (4)	0.5291 (3)	0.37337 (11)	0.0418 (6)
H3	0.9621	0.4705	0.3824	0.050*
C4	0.8825 (4)	0.6461 (3)	0.33613 (12)	0.0462 (7)
H4	0.9967	0.6696	0.3201	0.055*
C5	0.7411 (4)	0.7296 (3)	0.32160 (11)	0.0435 (7)
H5	0.7564	0.8094	0.2954	0.052*
C6	0.5733 (4)	0.6958 (3)	0.34586 (10)	0.0358 (6)
C7	0.3745 (4)	0.5491 (3)	0.41315 (11)	0.0386 (6)
H7A	0.3791	0.5938	0.4523	0.058*
H7B	0.3496	0.4380	0.4142	0.058*
H7C	0.2796	0.5945	0.3916	0.058*
C8	0.4571 (4)	0.0158 (3)	0.14518 (11)	0.0406 (6)
C9	0.4496 (4)	−0.0837 (3)	0.18974 (11)	0.0404 (6)
C10	0.5622 (4)	0.1097 (3)	0.25176 (12)	0.0412 (6)
C11	0.5713 (4)	0.2096 (3)	0.20717 (12)	0.0409 (6)
C12	0.3965 (5)	−0.0316 (4)	0.08584 (13)	0.0552 (8)
H12A	0.4153	0.0551	0.0609	0.083*
H12B	0.2690	−0.0639	0.0862	0.083*
H12C	0.4656	−0.1171	0.0715	0.083*
C13	0.3846 (5)	−0.2474 (3)	0.18159 (15)	0.0570 (8)
H13A	0.4104	−0.3023	0.2162	0.085*
H13B	0.4455	−0.2944	0.1488	0.085*
H13C	0.2551	−0.2532	0.1744	0.085*
C14	0.6179 (5)	0.1587 (4)	0.31122 (14)	0.0591 (9)
H14A	0.5880	0.0756	0.3370	0.089*
H14B	0.5550	0.2498	0.3234	0.089*
H14C	0.7474	0.1829	0.3124	0.089*
C15	0.6382 (5)	0.3730 (3)	0.21598 (16)	0.0557 (8)
H15A	0.6533	0.4195	0.1787	0.084*
H15B	0.7536	0.3776	0.2362	0.084*
H15C	0.5516	0.4291	0.2388	0.084*
C16	0.5885 (7)	0.3940 (4)	0.02995 (17)	0.0764 (14)
C17	0.4256 (7)	0.4388 (5)	0.04836 (17)	0.0781 (14)
C18	0.3345 (6)	0.5464 (4)	0.01903 (16)	0.0724 (13)
C19	0.1786 (8)	0.5809 (7)	0.0332 (2)	0.0449 (13)	0.5
H19A	0.1578	0.6847	0.0213	0.067*	0.5
H19B	0.1663	0.5768	0.0748	0.067*	0.5
H19C	0.0907	0.5078	0.0144	0.067*	0.5
C20	0.9897 (4)	0.0739 (3)	0.42562 (11)	0.0426 (7)
H20	0.8992	0.0264	0.4012	0.051*
C21	1.1426 (4)	−0.0024 (3)	0.43415 (11)	0.0403 (6)
H21	1.1564	−0.0999	0.4157	0.048*
C22	1.2775 (4)	0.0634 (3)	0.46990 (10)	0.0358 (6)
C23	1.2475 (4)	0.2058 (3)	0.49455 (12)	0.0429 (6)
H23	1.3350	0.2566	0.5193	0.052*
C24	1.0925 (4)	0.2731 (3)	0.48332 (12)	0.0456 (7)
H24	1.0765	0.3717	0.5006	0.055*
C25	1.4382 (4)	−0.0190 (3)	0.48023 (11)	0.0389 (6)
C26	−0.0613 (4)	−0.0830 (4)	0.16475 (13)	0.0469 (7)
C27	−0.1243 (5)	−0.2359 (4)	0.15087 (18)	0.0673 (10)
H27	−0.1291	−0.3098	0.1796	0.081*
C28	−0.1776 (6)	−0.2765 (6)	0.0968 (2)	0.0887 (16)
H28	−0.2179	−0.3798	0.0878	0.106*
C29	−0.1748 (6)	−0.1701 (6)	0.0537 (2)	0.0853 (15)
H29	−0.2108	−0.2019	0.0158	0.102*
C30	−0.1218 (6)	−0.0248 (5)	0.06557 (16)	0.0725 (11)
H30	−0.1240	0.0470	0.0362	0.087*
C31	−0.0621 (4)	0.0254 (4)	0.12115 (13)	0.0510 (8)
C32	−0.0004 (5)	0.1737 (4)	0.13456 (15)	0.0564 (8)
H32	0.0004	0.2483	0.1061	0.068*
C33	0.0598 (5)	0.2138 (4)	0.18861 (15)	0.0551 (9)
C34	0.1294 (6)	0.3637 (4)	0.2079 (2)	0.0805 (14)
H34	0.1378	0.4444	0.1819	0.097*
C35	0.1836 (6)	0.3904 (6)	0.2634 (3)	0.0937 (18)
H35	0.2246	0.4911	0.2759	0.112*
C36	0.1801 (6)	0.2740 (8)	0.3020 (2)	0.102 (2)
H36	0.2217	0.2950	0.3401	0.123*
C37	0.1195 (6)	0.1348 (6)	0.28604 (17)	0.0823 (13)
H37	0.1177	0.0565	0.3130	0.099*
C38	0.0569 (4)	0.0988 (4)	0.22963 (13)	0.0539 (8)
N1	0.5175 (3)	0.1613 (3)	0.15461 (10)	0.0425 (6)
N2	0.5004 (4)	−0.0352 (3)	0.24242 (10)	0.0433 (6)
N3	−0.0040 (4)	−0.0464 (3)	0.21761 (11)	0.0542 (7)
N4	0.9615 (3)	0.2109 (3)	0.44984 (9)	0.0413 (6)
O1	0.6684 (3)	0.3841 (2)	0.43529 (7)	0.0415 (5)
H1	0.7597	0.3325	0.4367	0.062*
O2	0.4279 (3)	0.7752 (2)	0.33323 (8)	0.0482 (5)
H2	0.4511	0.8301	0.3053	0.072*
O3	0.6583 (6)	0.3039 (5)	0.06205 (18)	0.0529 (10)*	0.5
H3A	0.5905	0.2870	0.0899	0.079*	0.5
O4	0.3688 (6)	0.3742 (5)	0.08905 (17)	0.0507 (10)*	0.5
H4A	0.4422	0.3110	0.0992	0.076*	0.5
H25	1.451 (4)	−0.113 (4)	0.4546 (13)	0.051 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0349 (14)	0.0324 (12)	0.0281 (11)	0.0038 (10)	−0.0005 (9)	−0.0026 (9)
C2	0.0386 (15)	0.0358 (13)	0.0293 (11)	0.0082 (11)	−0.0006 (9)	0.0010 (9)
C3	0.0345 (15)	0.0472 (15)	0.0451 (15)	0.0135 (12)	0.0037 (10)	0.0049 (11)
C4	0.0376 (16)	0.0522 (17)	0.0498 (16)	0.0076 (13)	0.0112 (11)	0.0083 (12)
C5	0.0482 (18)	0.0421 (14)	0.0417 (14)	0.0067 (13)	0.0090 (11)	0.0121 (11)
C6	0.0370 (14)	0.0380 (13)	0.0332 (12)	0.0076 (11)	0.0002 (9)	0.0017 (10)
C7	0.0303 (14)	0.0449 (14)	0.0407 (14)	0.0037 (11)	−0.0022 (10)	0.0029 (11)
C8	0.0370 (15)	0.0444 (15)	0.0409 (14)	0.0069 (12)	−0.0015 (10)	−0.0003 (11)
C9	0.0387 (16)	0.0378 (14)	0.0448 (14)	0.0047 (12)	−0.0031 (11)	0.0003 (11)
C10	0.0405 (16)	0.0379 (14)	0.0456 (15)	0.0067 (12)	−0.0081 (11)	0.0004 (11)
C11	0.0351 (15)	0.0377 (14)	0.0503 (15)	0.0055 (12)	−0.0031 (11)	0.0029 (11)
C12	0.054 (2)	0.071 (2)	0.0413 (15)	0.0080 (17)	−0.0055 (12)	−0.0035 (14)
C13	0.066 (2)	0.0385 (15)	0.065 (2)	−0.0016 (15)	−0.0065 (15)	−0.0028 (14)
C14	0.066 (2)	0.0586 (19)	0.0520 (18)	0.0060 (17)	−0.0223 (15)	−0.0049 (14)
C15	0.0433 (19)	0.0397 (16)	0.083 (2)	−0.0018 (14)	0.0013 (15)	0.0007 (15)
C16	0.101 (4)	0.057 (2)	0.069 (2)	−0.031 (2)	−0.041 (2)	0.0262 (18)
C17	0.111 (4)	0.058 (2)	0.063 (2)	−0.034 (2)	−0.040 (2)	0.0264 (17)
C18	0.101 (3)	0.0528 (19)	0.060 (2)	−0.030 (2)	−0.035 (2)	0.0119 (15)
C19	0.030 (3)	0.058 (4)	0.047 (3)	0.011 (3)	0.006 (2)	0.006 (2)
C20	0.0398 (16)	0.0498 (16)	0.0388 (14)	0.0081 (13)	−0.0093 (11)	0.0028 (11)
C21	0.0404 (16)	0.0409 (14)	0.0401 (13)	0.0077 (12)	−0.0052 (10)	0.0001 (11)
C22	0.0340 (14)	0.0364 (13)	0.0377 (13)	0.0051 (11)	−0.0024 (10)	0.0063 (10)
C23	0.0415 (16)	0.0344 (13)	0.0529 (16)	0.0042 (12)	−0.0091 (12)	0.0000 (11)
C24	0.0463 (18)	0.0353 (14)	0.0562 (17)	0.0099 (13)	−0.0040 (12)	0.0051 (12)
C25	0.0390 (16)	0.0351 (13)	0.0430 (14)	0.0069 (11)	−0.0063 (10)	0.0014 (11)
C26	0.0386 (17)	0.0483 (16)	0.0523 (17)	−0.0037 (13)	0.0114 (12)	−0.0089 (13)
C27	0.060 (2)	0.0534 (19)	0.086 (3)	−0.0131 (18)	0.0181 (18)	−0.0140 (18)
C28	0.061 (3)	0.086 (3)	0.112 (4)	−0.018 (2)	0.009 (2)	−0.056 (3)
C29	0.057 (3)	0.119 (4)	0.077 (3)	0.007 (3)	−0.0110 (19)	−0.043 (3)
C30	0.061 (2)	0.103 (3)	0.054 (2)	0.023 (2)	−0.0047 (16)	−0.015 (2)
C31	0.0389 (17)	0.064 (2)	0.0498 (17)	0.0062 (15)	0.0069 (12)	−0.0087 (14)
C32	0.053 (2)	0.0532 (18)	0.065 (2)	0.0102 (16)	0.0210 (15)	0.0096 (15)
C33	0.0426 (19)	0.0458 (16)	0.075 (2)	−0.0027 (14)	0.0258 (15)	−0.0140 (15)
C34	0.058 (2)	0.056 (2)	0.125 (4)	−0.0103 (19)	0.041 (2)	−0.023 (2)
C35	0.055 (3)	0.083 (3)	0.134 (4)	−0.020 (2)	0.038 (3)	−0.072 (3)
C36	0.058 (3)	0.141 (5)	0.099 (3)	−0.020 (3)	0.026 (2)	−0.071 (4)
C37	0.065 (3)	0.121 (4)	0.057 (2)	−0.007 (2)	0.0155 (17)	−0.037 (2)
C38	0.0403 (17)	0.067 (2)	0.0511 (17)	−0.0087 (15)	0.0176 (13)	−0.0189 (15)
N1	0.0429 (14)	0.0413 (12)	0.0445 (13)	0.0073 (11)	0.0014 (9)	0.0082 (10)
N2	0.0502 (16)	0.0367 (12)	0.0438 (13)	0.0056 (11)	−0.0084 (10)	0.0063 (9)
N3	0.0541 (17)	0.0596 (16)	0.0476 (14)	−0.0051 (14)	0.0139 (11)	−0.0027 (12)
N4	0.0372 (13)	0.0453 (13)	0.0430 (12)	0.0088 (10)	−0.0024 (9)	0.0126 (10)
O1	0.0412 (12)	0.0454 (11)	0.0401 (10)	0.0120 (9)	0.0046 (8)	0.0130 (8)
O2	0.0437 (13)	0.0522 (12)	0.0517 (12)	0.0146 (10)	0.0029 (8)	0.0209 (9)

Geometric parameters (Å, º)

C1—C6	1.386 (4)	C19—H19B	0.9800
C1—C2	1.386 (4)	C19—H19C	0.9800
C1—C7	1.492 (4)	C20—N4	1.331 (4)
C2—O1	1.358 (3)	C20—C21	1.373 (4)
C2—C3	1.394 (4)	C20—H20	0.9500
C3—C4	1.373 (4)	C21—C22	1.391 (4)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.366 (4)	C22—C23	1.380 (4)
C4—H4	0.9500	C22—C25	1.459 (4)
C5—C6	1.401 (4)	C23—C24	1.357 (4)
C5—H5	0.9500	C23—H23	0.9500
C6—O2	1.359 (4)	C24—N4	1.329 (4)
C7—H7A	0.9800	C24—H24	0.9500
C7—H7B	0.9800	C25—C25^ii	1.323 (5)
C7—H7C	0.9800	C25—H25	1.00 (3)
C8—N1	1.335 (4)	C26—N3	1.327 (4)
C8—C9	1.384 (4)	C26—C27	1.416 (5)
C8—C12	1.492 (4)	C26—C31	1.420 (5)
C9—N2	1.332 (4)	C27—C28	1.352 (6)
C9—C13	1.490 (4)	C27—H27	0.9500
C10—N2	1.333 (4)	C28—C29	1.398 (7)
C10—C11	1.387 (4)	C28—H28	0.9500
C10—C14	1.488 (4)	C29—C30	1.327 (7)
C11—N1	1.336 (4)	C29—H29	0.9500
C11—C15	1.492 (4)	C30—C31	1.416 (5)
C12—H12A	0.9800	C30—H30	0.9500
C12—H12B	0.9800	C31—C32	1.375 (5)
C12—H12C	0.9800	C32—C33	1.365 (5)
C13—H13A	0.9800	C32—H32	0.9500
C13—H13B	0.9800	C33—C38	1.417 (5)
C13—H13C	0.9800	C33—C34	1.436 (5)
C14—H14A	0.9800	C34—C35	1.365 (7)
C14—H14B	0.9800	C34—H34	0.9500
C14—H14C	0.9800	C35—C36	1.386 (8)
C15—H15A	0.9800	C35—H35	0.9500
C15—H15B	0.9800	C36—C37	1.313 (7)
C15—H15C	0.9800	C36—H36	0.9500
C16—O3	1.243 (6)	C37—C38	1.414 (5)
C16—C17	1.366 (7)	C37—H37	0.9500
C16—C18^i	1.391 (6)	C38—N3	1.342 (5)
C17—O4	1.194 (6)	O1—H1	0.8400
C17—C18	1.392 (6)	O2—H2	0.8400
C18—C19	1.262 (7)	O3—H3A	0.8400
C18—C16^i	1.392 (6)	O4—H4A	0.8400
C19—H19A	0.9800
C6—C1—C2	118.2 (2)	C18—C19—H19B	109.5
C6—C1—C7	121.5 (2)	H19A—C19—H19B	109.5
C2—C1—C7	120.3 (2)	C18—C19—H19C	109.5
O1—C2—C1	116.8 (2)	H19A—C19—H19C	109.5
O1—C2—C3	122.0 (2)	H19B—C19—H19C	109.5
C1—C2—C3	121.2 (3)	N4—C20—C21	123.4 (3)
C4—C3—C2	119.0 (3)	N4—C20—H20	118.3
C4—C3—H3	120.5	C21—C20—H20	118.3
C2—C3—H3	120.5	C20—C21—C22	119.8 (3)
C5—C4—C3	121.5 (3)	C20—C21—H21	120.1
C5—C4—H4	119.3	C22—C21—H21	120.1
C3—C4—H4	119.3	C23—C22—C21	116.3 (3)
C4—C5—C6	119.1 (3)	C23—C22—C25	123.7 (3)
C4—C5—H5	120.4	C21—C22—C25	120.0 (2)
C6—C5—H5	120.4	C24—C23—C22	119.7 (3)
O2—C6—C1	117.3 (2)	C24—C23—H23	120.1
O2—C6—C5	121.8 (2)	C22—C23—H23	120.1
C1—C6—C5	120.9 (2)	N4—C24—C23	124.6 (3)
C1—C7—H7A	109.5	N4—C24—H24	117.7
C1—C7—H7B	109.5	C23—C24—H24	117.7
H7A—C7—H7B	109.5	C25^ii—C25—C22	125.7 (3)
C1—C7—H7C	109.5	C25^ii—C25—H25	119.8 (19)
H7A—C7—H7C	109.5	C22—C25—H25	114.6 (19)
H7B—C7—H7C	109.5	N3—C26—C27	119.1 (3)
N1—C8—C9	120.1 (3)	N3—C26—C31	122.5 (3)
N1—C8—C12	117.3 (3)	C27—C26—C31	118.3 (3)
C9—C8—C12	122.6 (3)	C28—C27—C26	120.0 (4)
N2—C9—C8	120.5 (3)	C28—C27—H27	120.0
N2—C9—C13	117.2 (3)	C26—C27—H27	120.0
C8—C9—C13	122.3 (3)	C27—C28—C29	121.5 (4)
N2—C10—C11	120.3 (3)	C27—C28—H28	119.3
N2—C10—C14	117.6 (3)	C29—C28—H28	119.3
C11—C10—C14	122.1 (3)	C30—C29—C28	120.2 (4)
N1—C11—C10	120.1 (3)	C30—C29—H29	119.9
N1—C11—C15	118.0 (3)	C28—C29—H29	119.9
C10—C11—C15	121.9 (3)	C29—C30—C31	121.3 (4)
C8—C12—H12A	109.5	C29—C30—H30	119.3
C8—C12—H12B	109.5	C31—C30—H30	119.3
H12A—C12—H12B	109.5	C32—C31—C26	118.3 (3)
C8—C12—H12C	109.5	C32—C31—C30	123.0 (4)
H12A—C12—H12C	109.5	C26—C31—C30	118.6 (3)
H12B—C12—H12C	109.5	C33—C32—C31	120.1 (3)
C9—C13—H13A	109.5	C33—C32—H32	119.9
C9—C13—H13B	109.5	C31—C32—H32	119.9
H13A—C13—H13B	109.5	C32—C33—C38	118.1 (3)
C9—C13—H13C	109.5	C32—C33—C34	125.6 (4)
H13A—C13—H13C	109.5	C38—C33—C34	116.3 (4)
H13B—C13—H13C	109.5	C35—C34—C33	120.2 (4)
C10—C14—H14A	109.5	C35—C34—H34	119.9
C10—C14—H14B	109.5	C33—C34—H34	119.9
H14A—C14—H14B	109.5	C34—C35—C36	121.5 (4)
C10—C14—H14C	109.5	C34—C35—H35	119.2
H14A—C14—H14C	109.5	C36—C35—H35	119.2
H14B—C14—H14C	109.5	C37—C36—C35	120.2 (5)
C11—C15—H15A	109.5	C37—C36—H36	119.9
C11—C15—H15B	109.5	C35—C36—H36	119.9
H15A—C15—H15B	109.5	C36—C37—C38	121.6 (5)
C11—C15—H15C	109.5	C36—C37—H37	119.2
H15A—C15—H15C	109.5	C38—C37—H37	119.2
H15B—C15—H15C	109.5	N3—C38—C37	117.2 (4)
O3—C16—C17	113.6 (5)	N3—C38—C33	122.8 (3)
O3—C16—C18^i	125.8 (6)	C37—C38—C33	120.0 (3)
C17—C16—C18^i	120.6 (4)	C8—N1—C11	119.6 (2)
O4—C17—C16	114.6 (4)	C10—N2—C9	119.5 (2)
O4—C17—C18	124.6 (6)	C26—N3—C38	118.1 (3)
C16—C17—C18	120.7 (4)	C24—N4—C20	116.0 (3)
C19—C18—C16^i	119.7 (5)	C2—O1—H1	109.5
C19—C18—C17	121.4 (5)	C6—O2—H2	109.5
C16^i—C18—C17	118.7 (5)	C16—O3—H3A	109.5
C18—C19—H19A	109.5	C17—O4—H4A	109.5
C6—C1—C2—O1	−178.9 (2)	C31—C26—C27—C28	2.2 (5)
C7—C1—C2—O1	2.4 (3)	C26—C27—C28—C29	−1.0 (6)
C6—C1—C2—C3	1.1 (4)	C27—C28—C29—C30	−1.1 (7)
C7—C1—C2—C3	−177.6 (2)	C28—C29—C30—C31	1.9 (6)
O1—C2—C3—C4	−179.5 (2)	N3—C26—C31—C32	0.2 (5)
C1—C2—C3—C4	0.5 (4)	C27—C26—C31—C32	−179.8 (3)
C2—C3—C4—C5	−1.5 (4)	N3—C26—C31—C30	178.6 (3)
C3—C4—C5—C6	0.8 (4)	C27—C26—C31—C30	−1.4 (4)
C2—C1—C6—O2	179.3 (2)	C29—C30—C31—C32	177.7 (3)
C7—C1—C6—O2	−2.0 (3)	C29—C30—C31—C26	−0.6 (5)
C2—C1—C6—C5	−1.8 (4)	C26—C31—C32—C33	0.0 (5)
C7—C1—C6—C5	176.9 (2)	C30—C31—C32—C33	−178.2 (3)
C4—C5—C6—O2	179.7 (2)	C31—C32—C33—C38	0.2 (5)
C4—C5—C6—C1	0.9 (4)	C31—C32—C33—C34	179.2 (3)
N1—C8—C9—N2	0.8 (4)	C32—C33—C34—C35	179.1 (3)
C12—C8—C9—N2	−178.1 (3)	C38—C33—C34—C35	−1.8 (5)
N1—C8—C9—C13	−179.6 (3)	C33—C34—C35—C36	2.6 (6)
C12—C8—C9—C13	1.5 (5)	C34—C35—C36—C37	−1.8 (7)
N2—C10—C11—N1	0.2 (4)	C35—C36—C37—C38	0.2 (7)
C14—C10—C11—N1	−179.0 (3)	C36—C37—C38—N3	−179.4 (4)
N2—C10—C11—C15	179.4 (3)	C36—C37—C38—C33	0.5 (6)
C14—C10—C11—C15	0.1 (5)	C32—C33—C38—N3	−0.7 (5)
O3—C16—C17—O4	−6.6 (5)	C34—C33—C38—N3	−179.8 (3)
C18^i—C16—C17—O4	176.3 (4)	C32—C33—C38—C37	179.4 (3)
O3—C16—C17—C18	176.2 (3)	C34—C33—C38—C37	0.3 (5)
C18^i—C16—C17—C18	−0.9 (6)	C9—C8—N1—C11	0.3 (4)
O4—C17—C18—C19	−2.0 (7)	C12—C8—N1—C11	179.3 (3)
C16—C17—C18—C19	175.0 (4)	C10—C11—N1—C8	−0.8 (4)
O4—C17—C18—C16^i	−176.0 (4)	C15—C11—N1—C8	179.9 (3)
C16—C17—C18—C16^i	0.9 (6)	C11—C10—N2—C9	0.9 (4)
N4—C20—C21—C22	0.3 (4)	C14—C10—N2—C9	−179.8 (3)
C20—C21—C22—C23	−0.6 (4)	C8—C9—N2—C10	−1.4 (4)
C20—C21—C22—C25	178.4 (2)	C13—C9—N2—C10	179.0 (3)
C21—C22—C23—C24	0.2 (4)	C27—C26—N3—C38	179.3 (3)
C25—C22—C23—C24	−178.8 (3)	C31—C26—N3—C38	−0.7 (5)
C22—C23—C24—N4	0.7 (5)	C37—C38—N3—C26	−179.2 (3)
C23—C22—C25—C25^ii	10.3 (6)	C33—C38—N3—C26	1.0 (5)
C21—C22—C25—C25^ii	−168.6 (4)	C23—C24—N4—C20	−1.0 (5)
N3—C26—C27—C28	−177.8 (3)	C21—C20—N4—C24	0.5 (4)

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

(MRE_TMP_DPE-I_DP)

Crystal data

C46H48N4O4	V = 942 (2) Å^3
Mr = 720.88	Z = 1
Triclinic, P1	F(000) = 384
a = 7.528 (11) Å	Dx = 1.271 Mg m^−3
b = 8.948 (14) Å	Mo Kα radiation, λ = 0.71073 Å
c = 14.11 (2) Å	µ = 0.08 mm^−1
α = 96.219 (17)°	T = 150 K
β = 94.61 (2)°	Block, light green
γ = 90.598 (13)°	0.47 × 0.34 × 0.23 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2970 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.066
profile data from ω–scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.714, Tmax = 1.000	k = −11→11
8263 measured reflections	l = −17→17
3646 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.167	w = 1/[σ^2(Fo^2) + (0.0997P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3646 reflections	Δρmax = 0.25 e Å^−3
253 parameters	Δρmin = −0.24 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
H17	−0.444 (3)	1.107 (2)	0.5688 (14)	0.037 (5)*
O1	0.37218 (16)	0.63621 (13)	0.60508 (8)	0.0309 (3)
H1	0.2793	0.6870	0.6003	0.046*
O2	0.62466 (15)	0.25137 (14)	0.77458 (9)	0.0330 (3)
H2	0.6004	0.1963	0.8165	0.050*
N1	0.53636 (18)	0.08253 (15)	0.92627 (9)	0.0263 (3)
C1	0.4977 (2)	0.44128 (17)	0.68696 (10)	0.0232 (4)
C2	0.3483 (2)	0.52653 (17)	0.66374 (11)	0.0243 (4)
C6	0.4771 (2)	0.33145 (18)	0.74917 (11)	0.0256 (4)
C3	0.1851 (2)	0.5011 (2)	0.69874 (12)	0.0306 (4)
H3	0.0856	0.5602	0.6822	0.037*
C10	0.5637 (2)	0.14368 (18)	1.01764 (12)	0.0252 (4)
C23	0.9672 (2)	−0.07469 (19)	0.97608 (12)	0.0287 (4)
C4	0.1681 (2)	0.3885 (2)	0.75816 (13)	0.0343 (4)
H4	0.0559	0.3697	0.7814	0.041*
C9	0.4726 (2)	−0.05919 (18)	0.90782 (12)	0.0266 (4)
C11	0.6316 (2)	0.30416 (19)	1.03581 (14)	0.0354 (4)
H11A	0.6384	0.3456	0.9747	0.053*
H11B	0.7504	0.3072	1.0700	0.053*
H11C	0.5501	0.3640	1.0746	0.053*
C7	0.6709 (2)	0.4662 (2)	0.64450 (12)	0.0307 (4)
H7A	0.7675	0.4201	0.6813	0.046*
H7B	0.6951	0.5744	0.6466	0.046*
H7C	0.6630	0.4203	0.5780	0.046*
C8	0.4378 (3)	−0.1230 (2)	0.80494 (13)	0.0380 (4)
H8A	0.4734	−0.0489	0.7635	0.057*
H8B	0.3105	−0.1474	0.7911	0.057*
H8C	0.5068	−0.2145	0.7932	0.057*
C5	0.3129 (2)	0.3039 (2)	0.78373 (12)	0.0324 (4)
H5	0.3008	0.2275	0.8246	0.039*
C22	0.9334 (3)	−0.1943 (2)	1.02800 (14)	0.0424 (5)
H22	0.9544	−0.1808	1.0957	0.051*
C20	0.8407 (3)	−0.3572 (2)	0.88588 (14)	0.0403 (5)
H20	0.7975	−0.4519	0.8554	0.048*
C18	0.9363 (3)	−0.1024 (2)	0.87693 (13)	0.0412 (5)
H18	0.9575	−0.0238	0.8388	0.049*
C19	0.8756 (3)	−0.2408 (2)	0.83261 (14)	0.0458 (5)
H19	0.8577	−0.2562	0.7648	0.055*
C21	0.8695 (3)	−0.3332 (2)	0.98343 (15)	0.0459 (5)
H21	0.8458	−0.4119	1.0210	0.055*
N2	0.06357 (19)	0.80524 (16)	0.58357 (10)	0.0319 (4)
C14	−0.2680 (2)	0.94290 (18)	0.55156 (11)	0.0276 (4)
C12	0.0305 (2)	0.9421 (2)	0.62581 (12)	0.0328 (4)
H12	0.1230	0.9934	0.6669	0.039*
C13	−0.1302 (2)	1.0133 (2)	0.61317 (12)	0.0316 (4)
H13	−0.1470	1.1097	0.6462	0.038*
C15	−0.2336 (2)	0.8001 (2)	0.50744 (13)	0.0339 (4)
H15	−0.3226	0.7465	0.4651	0.041*
C17	−0.4360 (2)	1.0211 (2)	0.53399 (13)	0.0311 (4)
C16	−0.0699 (2)	0.7375 (2)	0.52561 (13)	0.0350 (4)
H16	−0.0503	0.6398	0.4951	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0336 (7)	0.0315 (7)	0.0299 (6)	0.0087 (5)	0.0053 (5)	0.0117 (5)
O2	0.0278 (6)	0.0381 (7)	0.0369 (7)	0.0112 (5)	0.0070 (5)	0.0171 (5)
N1	0.0240 (7)	0.0249 (7)	0.0309 (7)	0.0032 (6)	0.0010 (6)	0.0073 (5)
C1	0.0246 (8)	0.0242 (8)	0.0204 (7)	0.0009 (6)	0.0018 (6)	0.0005 (6)
C2	0.0300 (8)	0.0226 (8)	0.0201 (7)	0.0029 (6)	0.0014 (6)	0.0021 (6)
C6	0.0253 (8)	0.0259 (8)	0.0258 (8)	0.0059 (6)	0.0014 (6)	0.0041 (6)
C3	0.0268 (9)	0.0328 (9)	0.0334 (9)	0.0101 (7)	0.0032 (7)	0.0084 (7)
C10	0.0207 (8)	0.0231 (8)	0.0323 (8)	0.0030 (6)	0.0006 (6)	0.0054 (6)
C23	0.0227 (8)	0.0325 (10)	0.0317 (9)	0.0044 (7)	0.0073 (6)	0.0027 (7)
C4	0.0259 (9)	0.0408 (11)	0.0394 (10)	0.0055 (7)	0.0089 (7)	0.0139 (8)
C9	0.0226 (8)	0.0260 (8)	0.0311 (9)	0.0044 (6)	−0.0002 (6)	0.0045 (6)
C11	0.0359 (10)	0.0247 (9)	0.0455 (10)	−0.0024 (7)	0.0023 (8)	0.0044 (7)
C7	0.0274 (9)	0.0360 (10)	0.0300 (9)	0.0005 (7)	0.0052 (7)	0.0076 (7)
C8	0.0426 (11)	0.0392 (11)	0.0312 (9)	0.0007 (8)	−0.0011 (8)	0.0020 (8)
C5	0.0315 (9)	0.0339 (10)	0.0353 (9)	0.0055 (7)	0.0086 (7)	0.0144 (7)
C22	0.0482 (12)	0.0446 (12)	0.0350 (10)	−0.0145 (9)	0.0107 (8)	0.0039 (8)
C20	0.0337 (10)	0.0364 (11)	0.0491 (11)	−0.0009 (8)	0.0093 (8)	−0.0066 (8)
C18	0.0554 (12)	0.0349 (10)	0.0332 (10)	0.0043 (9)	0.0041 (9)	0.0027 (8)
C19	0.0562 (13)	0.0435 (12)	0.0354 (10)	0.0052 (10)	0.0026 (9)	−0.0060 (8)
C21	0.0486 (12)	0.0422 (12)	0.0483 (12)	−0.0143 (9)	0.0126 (9)	0.0059 (9)
N2	0.0301 (8)	0.0329 (8)	0.0348 (8)	0.0067 (6)	0.0021 (6)	0.0134 (6)
C14	0.0286 (9)	0.0270 (9)	0.0287 (8)	0.0036 (7)	0.0032 (7)	0.0089 (6)
C12	0.0310 (9)	0.0372 (10)	0.0303 (9)	0.0021 (7)	−0.0030 (7)	0.0085 (7)
C13	0.0341 (9)	0.0309 (9)	0.0294 (9)	0.0065 (7)	−0.0001 (7)	0.0027 (7)
C15	0.0328 (9)	0.0266 (9)	0.0411 (10)	0.0019 (7)	−0.0045 (8)	0.0034 (7)
C17	0.0315 (9)	0.0267 (9)	0.0351 (9)	0.0071 (7)	0.0010 (7)	0.0036 (7)
C16	0.0370 (10)	0.0247 (9)	0.0437 (10)	0.0065 (7)	0.0008 (8)	0.0069 (7)

Geometric parameters (Å, º)

O1—C2	1.370 (2)	C7—H7C	0.9800
O1—H1	0.8400	C8—H8A	0.9800
O2—C6	1.373 (2)	C8—H8B	0.9800
O2—H2	0.8400	C8—H8C	0.9800
N1—C9	1.342 (3)	C5—H5	0.9500
N1—C10	1.344 (3)	C22—C21	1.392 (3)
C1—C6	1.402 (3)	C22—H22	0.9500
C1—C2	1.403 (3)	C20—C21	1.369 (3)
C1—C7	1.502 (3)	C20—C19	1.384 (3)
C2—C3	1.386 (3)	C20—H20	0.9500
C6—C5	1.394 (3)	C18—C19	1.381 (3)
C3—C4	1.390 (3)	C18—H18	0.9500
C3—H3	0.9500	C19—H19	0.9500
C10—C9^i	1.402 (3)	C21—H21	0.9500
C10—C11	1.508 (3)	N2—C12	1.338 (3)
C23—C22	1.394 (3)	N2—C16	1.340 (3)
C23—C18	1.395 (3)	C14—C15	1.395 (3)
C23—C23^ii	1.491 (4)	C14—C13	1.397 (3)
C4—C5	1.380 (3)	C14—C17	1.468 (3)
C4—H4	0.9500	C12—C13	1.381 (3)
C9—C10^i	1.402 (3)	C12—H12	0.9500
C9—C8	1.503 (3)	C13—H13	0.9500
C11—H11A	0.9800	C15—C16	1.376 (3)
C11—H11B	0.9800	C15—H15	0.9500
C11—H11C	0.9800	C17—C17^iii	1.326 (4)
C7—H7A	0.9800	C17—H17	0.87 (2)
C7—H7B	0.9800	C16—H16	0.9500
C2—O1—H1	109.5	H8A—C8—H8B	109.5
C6—O2—H2	109.5	C9—C8—H8C	109.5
C9—N1—C10	119.06 (14)	H8A—C8—H8C	109.5
C6—C1—C2	117.42 (16)	H8B—C8—H8C	109.5
C6—C1—C7	122.04 (15)	C4—C5—C6	119.56 (17)
C2—C1—C7	120.53 (17)	C4—C5—H5	120.2
O1—C2—C3	121.86 (15)	C6—C5—H5	120.2
O1—C2—C1	116.61 (16)	C21—C22—C23	121.8 (2)
C3—C2—C1	121.53 (17)	C21—C22—H22	119.1
O2—C6—C5	121.11 (16)	C23—C22—H22	119.1
O2—C6—C1	117.53 (15)	C21—C20—C19	118.71 (19)
C5—C6—C1	121.36 (15)	C21—C20—H20	120.6
C2—C3—C4	119.55 (16)	C19—C20—H20	120.6
C2—C3—H3	120.2	C19—C18—C23	121.85 (18)
C4—C3—H3	120.2	C19—C18—H18	119.1
N1—C10—C9^i	120.04 (18)	C23—C18—H18	119.1
N1—C10—C11	117.73 (15)	C18—C19—C20	120.7 (2)
C9^i—C10—C11	122.22 (17)	C18—C19—H19	119.6
C22—C23—C18	116.31 (18)	C20—C19—H19	119.6
C22—C23—C23^ii	121.8 (2)	C20—C21—C22	120.56 (19)
C18—C23—C23^ii	121.85 (19)	C20—C21—H21	119.7
C5—C4—C3	120.53 (17)	C22—C21—H21	119.7
C5—C4—H4	119.7	C12—N2—C16	116.13 (16)
C3—C4—H4	119.7	C15—C14—C13	116.47 (17)
N1—C9—C10^i	120.89 (16)	C15—C14—C17	123.51 (16)
N1—C9—C8	117.93 (15)	C13—C14—C17	120.00 (18)
C10^i—C9—C8	121.17 (18)	N2—C12—C13	123.85 (16)
C10—C11—H11A	109.5	N2—C12—H12	118.1
C10—C11—H11B	109.5	C13—C12—H12	118.1
H11A—C11—H11B	109.5	C12—C13—C14	119.71 (18)
C10—C11—H11C	109.5	C12—C13—H13	120.1
H11A—C11—H11C	109.5	C14—C13—H13	120.1
H11B—C11—H11C	109.5	C16—C15—C14	119.57 (17)
C1—C7—H7A	109.5	C16—C15—H15	120.2
C1—C7—H7B	109.5	C14—C15—H15	120.2
H7A—C7—H7B	109.5	C17^iii—C17—C14	125.9 (2)
C1—C7—H7C	109.5	C17^iii—C17—H17	119.0 (13)
H7A—C7—H7C	109.5	C14—C17—H17	114.9 (13)
H7B—C7—H7C	109.5	N2—C16—C15	124.26 (18)
C9—C8—H8A	109.5	N2—C16—H16	117.9
C9—C8—H8B	109.5	C15—C16—H16	117.9

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1	0.95	2.63	3.345 (4)	132

(MRE_TMP_DPE-II_22BP)

Crystal data

C44H48N6O4	V = 932.0 (3) Å^3
Mr = 724.88	Z = 1
Triclinic, P1	F(000) = 386
a = 7.4957 (13) Å	Dx = 1.292 Mg m^−3
b = 8.7882 (17) Å	Mo Kα radiation, λ = 0.71073 Å
c = 14.308 (3) Å	µ = 0.08 mm^−1
α = 97.049 (11)°	T = 150 K
β = 94.334 (13)°	Block, colorless
γ = 91.781 (10)°	0.45 × 0.35 × 0.24 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3702 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.108
profile data from ω–scans	θmax = 27.6°, θmin = 1.4°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.791, Tmax = 1.000	k = −11→11
10002 measured reflections	l = −18→18
4287 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.181	w = 1/[σ^2(Fo^2) + (0.0854P)^2 + 0.1366P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
4287 reflections	Δρmax = 0.31 e Å^−3
257 parameters	Δρmin = −0.35 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
H17A	1.479 (3)	−0.585 (3)	0.4080 (16)	0.041 (6)*
H17B	1.569 (3)	−0.406 (3)	0.4287 (17)	0.046 (6)*
O1	0.39213 (15)	0.24678 (13)	0.22096 (8)	0.0273 (3)
H1	0.4138	0.2999	0.1779	0.041*
O2	0.65263 (15)	−0.12469 (13)	0.39418 (8)	0.0258 (3)
H2	0.7422	−0.1798	0.3955	0.039*
N1	0.46322 (16)	0.41704 (14)	0.07248 (9)	0.0215 (3)
N2	0.94292 (18)	−0.30944 (16)	0.41538 (10)	0.0266 (3)
C1	0.52452 (19)	0.06309 (16)	0.30928 (10)	0.0187 (3)
C2	0.54165 (19)	0.17141 (16)	0.24587 (10)	0.0201 (3)
C9	0.43035 (19)	0.35469 (16)	−0.01755 (11)	0.0205 (3)
C5	0.8391 (2)	0.00808 (18)	0.29678 (11)	0.0244 (3)
H5	0.9400	−0.0486	0.3135	0.029*
C4	0.8531 (2)	0.11930 (18)	0.23582 (12)	0.0265 (3)
H4	0.9651	0.1394	0.2119	0.032*
C14	1.2860 (2)	−0.42917 (18)	0.43745 (11)	0.0235 (3)
C6	0.6746 (2)	−0.01893 (16)	0.33300 (10)	0.0201 (3)
C3	0.7068 (2)	0.20063 (17)	0.20973 (11)	0.0244 (3)
H3	0.7177	0.2756	0.1678	0.029*
C16	0.9781 (2)	−0.44921 (18)	0.37486 (12)	0.0277 (4)
H16	0.8838	−0.5085	0.3380	0.033*
C10	0.53360 (19)	0.56087 (16)	0.09161 (11)	0.0211 (3)
C15	1.1446 (2)	−0.51251 (18)	0.38353 (12)	0.0273 (3)
H15	1.1624	−0.6124	0.3528	0.033*
C11	0.5729 (2)	0.6247 (2)	0.19333 (12)	0.0303 (4)
H11A	0.5253	0.5531	0.2335	0.045*
H11B	0.5165	0.7236	0.2054	0.045*
H11C	0.7027	0.6393	0.2076	0.045*
C7	0.3505 (2)	0.03710 (18)	0.35287 (11)	0.0248 (3)
H7A	0.3203	−0.0732	0.3467	0.037*
H7B	0.2549	0.0890	0.3203	0.037*
H7C	0.3633	0.0786	0.4199	0.037*
C8	0.3547 (2)	0.19253 (17)	−0.03538 (13)	0.0301 (4)
H8A	0.3370	0.1548	0.0251	0.045*
H8B	0.4382	0.1274	−0.0698	0.045*
H8C	0.2397	0.1895	−0.0731	0.045*
C17	1.4720 (2)	−0.4894 (2)	0.44871 (12)	0.0296 (4)
C13	1.2483 (2)	−0.28552 (19)	0.48095 (13)	0.0301 (4)
H13	1.3392	−0.2245	0.5194	0.036*
C12	1.0784 (2)	−0.23107 (18)	0.46844 (12)	0.0296 (4)
H12	1.0563	−0.1322	0.4993	0.035*
N3	0.07827 (19)	0.68570 (15)	0.97510 (10)	0.0298 (3)
C18	0.03678 (19)	0.57365 (17)	1.02683 (11)	0.0231 (3)
C20	0.1279 (2)	0.7310 (2)	1.17150 (13)	0.0328 (4)
H20	0.1452	0.7465	1.2385	0.039*
C19	0.0604 (2)	0.59174 (19)	1.12501 (12)	0.0281 (4)
H19	0.0307	0.5099	1.1594	0.034*
C21	0.1702 (2)	0.84809 (19)	1.11908 (13)	0.0325 (4)
H21	0.2164	0.9451	1.1493	0.039*
C22	0.1436 (2)	0.81987 (19)	1.02186 (13)	0.0332 (4)
H22	0.1732	0.9000	0.9861	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0234 (6)	0.0313 (6)	0.0308 (6)	0.0063 (4)	0.0041 (5)	0.0161 (5)
O2	0.0257 (6)	0.0269 (6)	0.0278 (6)	0.0061 (4)	0.0044 (5)	0.0135 (5)
N1	0.0206 (6)	0.0195 (6)	0.0251 (7)	−0.0003 (5)	0.0003 (5)	0.0070 (5)
N2	0.0238 (7)	0.0286 (7)	0.0293 (7)	0.0043 (5)	0.0004 (5)	0.0115 (5)
C1	0.0196 (7)	0.0189 (6)	0.0175 (7)	−0.0017 (5)	0.0012 (5)	0.0028 (5)
C2	0.0207 (7)	0.0189 (6)	0.0206 (7)	0.0001 (5)	0.0006 (5)	0.0036 (5)
C9	0.0184 (6)	0.0168 (6)	0.0265 (7)	−0.0002 (5)	−0.0001 (5)	0.0053 (5)
C5	0.0184 (7)	0.0271 (7)	0.0285 (8)	0.0042 (6)	0.0012 (6)	0.0060 (6)
C4	0.0208 (7)	0.0293 (8)	0.0307 (8)	−0.0006 (6)	0.0063 (6)	0.0073 (6)
C14	0.0239 (7)	0.0260 (7)	0.0216 (7)	0.0033 (6)	0.0001 (6)	0.0071 (6)
C6	0.0229 (7)	0.0183 (6)	0.0193 (7)	0.0001 (5)	0.0004 (5)	0.0041 (5)
C3	0.0252 (8)	0.0228 (7)	0.0266 (8)	−0.0019 (6)	0.0056 (6)	0.0078 (6)
C16	0.0241 (8)	0.0278 (8)	0.0306 (8)	−0.0018 (6)	−0.0039 (6)	0.0065 (6)
C10	0.0188 (7)	0.0202 (7)	0.0244 (7)	0.0001 (5)	0.0001 (5)	0.0045 (6)
C15	0.0300 (8)	0.0235 (7)	0.0273 (8)	0.0039 (6)	−0.0027 (6)	0.0012 (6)
C11	0.0334 (9)	0.0307 (8)	0.0255 (8)	−0.0018 (7)	−0.0017 (7)	0.0023 (6)
C7	0.0200 (7)	0.0297 (8)	0.0263 (8)	−0.0014 (6)	0.0029 (6)	0.0093 (6)
C8	0.0307 (8)	0.0200 (7)	0.0390 (9)	−0.0063 (6)	0.0002 (7)	0.0050 (6)
C17	0.0254 (8)	0.0372 (9)	0.0265 (9)	0.0086 (7)	−0.0010 (6)	0.0056 (7)
C13	0.0278 (8)	0.0258 (8)	0.0349 (9)	0.0009 (6)	−0.0075 (7)	0.0024 (7)
C12	0.0329 (9)	0.0215 (7)	0.0338 (9)	0.0070 (6)	−0.0028 (7)	0.0033 (6)
N3	0.0327 (7)	0.0256 (7)	0.0311 (7)	−0.0076 (6)	0.0069 (6)	0.0036 (6)
C18	0.0189 (7)	0.0229 (7)	0.0278 (8)	−0.0008 (6)	0.0061 (6)	0.0017 (6)
C20	0.0313 (8)	0.0352 (9)	0.0300 (9)	−0.0026 (7)	0.0042 (7)	−0.0039 (7)
C19	0.0286 (8)	0.0265 (8)	0.0292 (8)	−0.0019 (6)	0.0056 (6)	0.0029 (6)
C21	0.0272 (8)	0.0272 (8)	0.0407 (10)	−0.0064 (6)	0.0073 (7)	−0.0058 (7)
C22	0.0342 (9)	0.0255 (8)	0.0395 (10)	−0.0096 (7)	0.0095 (7)	0.0017 (7)

Geometric parameters (Å, º)

O1—C2	1.3659 (18)	C14—C13	1.385 (2)
O2—C6	1.3671 (18)	C14—C15	1.394 (2)
N1—C9	1.338 (2)	C14—C17	1.511 (2)
N1—C10	1.3426 (18)	C16—C15	1.385 (2)
N2—C16	1.335 (2)	C10—C9^i	1.404 (2)
N2—C12	1.339 (2)	C10—C11	1.498 (2)
C1—C6	1.397 (2)	C17—C17^ii	1.531 (3)
C1—C2	1.403 (2)	C13—C12	1.381 (2)
C1—C7	1.5109 (19)	N3—C22	1.341 (2)
C2—C3	1.406 (2)	N3—C18	1.345 (2)
C9—C10^i	1.404 (2)	C18—C19	1.391 (2)
C9—C8	1.5020 (19)	C18—C18^iii	1.489 (3)
C5—C4	1.394 (2)	C20—C19	1.381 (2)
C5—C6	1.398 (2)	C20—C21	1.388 (3)
C4—C3	1.380 (2)	C21—C22	1.381 (3)
C9—N1—C10	119.39 (13)	C1—C6—C5	121.35 (14)
C16—N2—C12	116.30 (14)	C4—C3—C2	119.34 (14)
C6—C1—C2	118.20 (13)	N2—C16—C15	123.62 (14)
C6—C1—C7	120.36 (13)	N1—C10—C9^i	120.05 (14)
C2—C1—C7	121.43 (14)	N1—C10—C11	117.66 (14)
O1—C2—C1	117.43 (12)	C9^i—C10—C11	122.28 (13)
O1—C2—C3	121.63 (13)	C16—C15—C14	119.79 (14)
C1—C2—C3	120.94 (14)	C14—C17—C17^ii	112.22 (17)
N1—C9—C10^i	120.55 (13)	C12—C13—C14	119.93 (15)
N1—C9—C8	117.44 (14)	N2—C12—C13	123.84 (14)
C10^i—C9—C8	122.01 (14)	C22—N3—C18	117.39 (15)
C4—C5—C6	119.10 (15)	N3—C18—C19	122.79 (14)
C3—C4—C5	121.04 (14)	N3—C18—C18^iii	116.26 (18)
C13—C14—C15	116.49 (15)	C19—C18—C18^iii	120.95 (18)
C13—C14—C17	120.72 (14)	C19—C20—C21	119.16 (16)
C15—C14—C17	122.79 (14)	C20—C19—C18	118.70 (16)
O2—C6—C1	116.65 (12)	C22—C21—C20	118.29 (15)
O2—C6—C5	121.99 (14)	N3—C22—C21	123.67 (16)
C6—C1—C2—O1	177.82 (12)	C9—N1—C10—C11	−178.38 (13)
C7—C1—C2—O1	−3.5 (2)	N2—C16—C15—C14	0.4 (3)
C6—C1—C2—C3	−2.2 (2)	C13—C14—C15—C16	0.9 (2)
C7—C1—C2—C3	176.49 (13)	C17—C14—C15—C16	−178.87 (15)
C10—N1—C9—C10^i	−0.9 (2)	C13—C14—C17—C17^ii	63.6 (3)
C10—N1—C9—C8	178.91 (13)	C15—C14—C17—C17^ii	−116.6 (2)
C6—C5—C4—C3	−1.1 (2)	C15—C14—C13—C12	−1.0 (2)
C2—C1—C6—O2	−179.32 (12)	C17—C14—C13—C12	178.77 (15)
C7—C1—C6—O2	1.95 (19)	C16—N2—C12—C13	1.4 (2)
C2—C1—C6—C5	1.6 (2)	C14—C13—C12—N2	−0.2 (3)
C7—C1—C6—C5	−177.13 (14)	C22—N3—C18—C19	−0.6 (2)
C4—C5—C6—O2	−179.00 (13)	C22—N3—C18—C18^iii	179.54 (17)
C4—C5—C6—C1	0.0 (2)	C21—C20—C19—C18	−0.1 (3)
C5—C4—C3—C2	0.5 (2)	N3—C18—C19—C20	0.6 (3)
O1—C2—C3—C4	−178.82 (13)	C18^iii—C18—C19—C20	−179.55 (18)
C1—C2—C3—C4	1.2 (2)	C19—C20—C21—C22	−0.3 (3)
C12—N2—C16—C15	−1.5 (2)	C18—N3—C22—C21	0.1 (3)
C9—N1—C10—C9^i	0.9 (2)	C20—C21—C22—N3	0.3 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.98	2.8174 (17)	178
O2—H2···N2	0.84	1.94	2.7755 (18)	173
C3—H3···N1	0.95	2.69	3.376 (2)	130
C3—H3···N3^iv	0.95	2.69	3.432 (2)	135
O1—H1···N1	0.84	1.98	2.8174 (17)	178
O2—H2···N2	0.84	1.94	2.7755 (18)	173
C3—H3···N1	0.95	2.69	3.376 (2)	130
C3—H3···N3^iv	0.95	2.69	3.432 (2)	135

Symmetry code: (iv) −x+1, −y+1, −z+1.

(MRE_TMP_DPE-II_22TP)

Crystal data

C42H46N4O4S2	V = 937 (2) Å^3
Mr = 734.95	Z = 1
Triclinic, P1	F(000) = 390
a = 7.531 (9) Å	Dx = 1.302 Mg m^−3
b = 9.026 (12) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.941 (17) Å	µ = 0.19 mm^−1
α = 98.18 (2)°	T = 150 K
β = 92.03 (3)°	Block, colorless
γ = 91.235 (12)°	0.39 × 0.22 × 0.15 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3059 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.061
profile data from ω–scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.622, Tmax = 1.000	k = −11→11
8797 measured reflections	l = −17→17
3673 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.082	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.282	w = 1/[σ^2(Fo^2) + (0.1017P)^2 + 3.9487P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.004
3673 reflections	Δρmax = 0.51 e Å^−3
248 parameters	Δρmin = −0.52 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C17	0.0468 (10)	−0.0232 (11)	−0.0427 (5)	0.067 (3)
H17A	0.006 (10)	−0.079 (9)	−0.087 (6)	0.06 (2)*
H17B	−0.032 (13)	0.072 (11)	−0.055 (7)	0.09 (3)*
S1	0.42951 (19)	0.81287 (15)	0.38463 (10)	0.0345 (4)
C21	0.4663 (6)	0.9227 (5)	0.4964 (4)	0.0256 (10)
C20	0.4245 (6)	0.8436 (5)	0.5723 (4)	0.0282 (10)
H20	0.4346	0.8840	0.6391	0.034*
C19	0.3640 (7)	0.6928 (6)	0.5359 (4)	0.0336 (11)
H19	0.3307	0.6216	0.5765	0.040*
C18	0.3595 (7)	0.6629 (6)	0.4364 (4)	0.0335 (12)
H18	0.3218	0.5693	0.4006	0.040*
O1	0.1510 (4)	0.6445 (4)	0.1150 (3)	0.0315 (8)
H1	0.2433	0.6980	0.1140	0.047*
O2	−0.0732 (4)	0.2616 (4)	0.2798 (3)	0.0280 (8)
H2	−0.0435	0.2192	0.3276	0.042*
C4	0.3878 (6)	0.3731 (5)	0.2412 (3)	0.0256 (10)
H4	0.5058	0.3455	0.2555	0.031*
C2	0.1859 (6)	0.5301 (5)	0.1675 (3)	0.0235 (10)
C1	0.0393 (6)	0.4497 (5)	0.1955 (3)	0.0230 (9)
C5	0.2452 (6)	0.2939 (5)	0.2721 (3)	0.0265 (10)
H5	0.2656	0.2136	0.3081	0.032*
N2	0.5483 (5)	0.1927 (5)	−0.0875 (3)	0.0285 (9)
C15	0.5043 (7)	0.0515 (6)	−0.1293 (4)	0.0280 (10)
H15	0.5875	−0.0016	−0.1698	0.034*
C6	0.0717 (6)	0.3334 (5)	0.2499 (3)	0.0226 (9)
C3	0.3600 (6)	0.4917 (5)	0.1898 (3)	0.0242 (10)
H3	0.4581	0.5463	0.1699	0.029*
C12	0.2199 (7)	0.0547 (6)	−0.0574 (4)	0.0315 (11)
C16	0.3462 (7)	−0.0185 (6)	−0.1162 (4)	0.0303 (11)
H16	0.3221	−0.1178	−0.1475	0.036*
C13	0.2660 (7)	0.1995 (6)	−0.0133 (4)	0.0326 (11)
H13	0.1861	0.2543	0.0285	0.039*
C14	0.4281 (7)	0.2628 (6)	−0.0305 (4)	0.0304 (11)
H14	0.4557	0.3620	−0.0001	0.036*
C7	−0.1488 (6)	0.4859 (6)	0.1676 (4)	0.0324 (11)
H7A	−0.2136	0.3935	0.1399	0.049*
H7B	−0.1466	0.5552	0.1195	0.049*
H7C	−0.2081	0.5324	0.2253	0.049*
N1	−0.0129 (5)	0.9171 (4)	0.5758 (3)	0.0242 (8)
C10	0.0347 (6)	1.0637 (5)	0.5933 (3)	0.0233 (9)
C9	−0.0485 (6)	0.8526 (5)	0.4834 (3)	0.0230 (9)
C11	0.0704 (8)	1.1326 (6)	0.6966 (4)	0.0360 (12)
H11A	0.0649	1.0545	0.7387	0.054*
H11B	−0.0192	1.2073	0.7153	0.054*
H11C	0.1888	1.1810	0.7034	0.054*
C8	−0.1060 (7)	0.6904 (5)	0.4686 (4)	0.0291 (11)
H8A	−0.0713	0.6454	0.5263	0.044*
H8B	−0.0487	0.6379	0.4120	0.044*
H8C	−0.2354	0.6819	0.4581	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C17	0.057 (4)	0.090 (6)	0.040 (4)	−0.051 (5)	0.024 (3)	−0.034 (4)
S1	0.0416 (8)	0.0310 (7)	0.0296 (7)	−0.0022 (5)	−0.0005 (5)	0.0005 (5)
C21	0.023 (2)	0.023 (2)	0.030 (2)	0.0034 (18)	−0.0029 (18)	0.0018 (19)
C20	0.029 (2)	0.022 (2)	0.035 (3)	0.0010 (19)	−0.002 (2)	0.008 (2)
C19	0.035 (3)	0.027 (3)	0.038 (3)	0.001 (2)	0.001 (2)	0.005 (2)
C18	0.035 (3)	0.024 (2)	0.040 (3)	0.000 (2)	−0.001 (2)	0.002 (2)
O1	0.0263 (17)	0.0318 (19)	0.040 (2)	−0.0053 (14)	0.0004 (15)	0.0190 (16)
O2	0.0288 (17)	0.0260 (17)	0.0321 (19)	−0.0064 (14)	−0.0015 (14)	0.0159 (14)
C4	0.025 (2)	0.026 (2)	0.026 (2)	0.0013 (18)	−0.0012 (18)	0.0033 (19)
C2	0.028 (2)	0.020 (2)	0.023 (2)	−0.0039 (18)	0.0000 (18)	0.0034 (17)
C1	0.025 (2)	0.021 (2)	0.024 (2)	−0.0011 (18)	−0.0006 (18)	0.0056 (18)
C5	0.030 (2)	0.025 (2)	0.026 (2)	0.0005 (19)	−0.0003 (19)	0.0097 (19)
N2	0.028 (2)	0.026 (2)	0.033 (2)	−0.0047 (17)	0.0012 (17)	0.0111 (17)
C15	0.031 (2)	0.029 (2)	0.025 (2)	−0.001 (2)	0.0018 (19)	0.0034 (19)
C6	0.026 (2)	0.019 (2)	0.022 (2)	−0.0040 (17)	0.0013 (18)	0.0038 (17)
C3	0.026 (2)	0.021 (2)	0.026 (2)	−0.0031 (18)	0.0034 (18)	0.0027 (18)
C12	0.032 (3)	0.032 (3)	0.029 (3)	−0.013 (2)	0.002 (2)	0.001 (2)
C16	0.037 (3)	0.029 (3)	0.024 (2)	−0.010 (2)	0.000 (2)	0.0003 (19)
C13	0.033 (3)	0.033 (3)	0.031 (3)	−0.005 (2)	0.007 (2)	0.002 (2)
C14	0.037 (3)	0.024 (2)	0.030 (3)	−0.009 (2)	0.003 (2)	0.005 (2)
C7	0.026 (2)	0.030 (3)	0.043 (3)	−0.004 (2)	−0.005 (2)	0.014 (2)
N1	0.028 (2)	0.0194 (19)	0.027 (2)	−0.0010 (15)	−0.0012 (16)	0.0087 (15)
C10	0.025 (2)	0.018 (2)	0.028 (2)	0.0007 (17)	0.0005 (18)	0.0035 (18)
C9	0.023 (2)	0.015 (2)	0.032 (2)	0.0007 (17)	0.0014 (18)	0.0065 (18)
C11	0.051 (3)	0.030 (3)	0.027 (3)	−0.005 (2)	−0.002 (2)	0.006 (2)
C8	0.035 (3)	0.015 (2)	0.037 (3)	−0.0038 (19)	−0.002 (2)	0.0057 (19)

Geometric parameters (Å, º)

C17—C17^i	1.420 (13)	N2—C14	1.335 (7)
C17—C12	1.502 (8)	N2—C15	1.354 (7)
C17—H17A	0.79 (8)	C15—C16	1.366 (7)
C17—H17B	1.08 (10)	C15—H15	0.9500
S1—C18	1.705 (6)	C3—H3	0.9500
S1—C21	1.733 (5)	C12—C16	1.393 (8)
C21—C20	1.399 (7)	C12—C13	1.394 (7)
C21—C21^ii	1.463 (10)	C16—H16	0.9500
C20—C19	1.441 (7)	C13—C14	1.380 (7)
C20—H20	0.9500	C13—H13	0.9500
C19—C18	1.374 (8)	C14—H14	0.9500
C19—H19	0.9500	C7—H7A	0.9800
C18—H18	0.9500	C7—H7B	0.9800
O1—C2	1.372 (6)	C7—H7C	0.9800
O1—H1	0.8400	N1—C10	1.349 (6)
O2—C6	1.366 (6)	N1—C9	1.352 (6)
O2—H2	0.8400	C10—C9^iii	1.400 (7)
C4—C3	1.386 (7)	C10—C11	1.498 (7)
C4—C5	1.392 (7)	C9—C10^iii	1.400 (7)
C4—H4	0.9500	C9—C8	1.501 (6)
C2—C3	1.399 (7)	C11—H11A	0.9800
C2—C1	1.405 (6)	C11—H11B	0.9800
C1—C6	1.400 (6)	C11—H11C	0.9800
C1—C7	1.510 (7)	C8—H8A	0.9800
C5—C6	1.397 (7)	C8—H8B	0.9800
C5—H5	0.9500	C8—H8C	0.9800
C17^i—C17—C12	119.1 (7)	C4—C3—C2	119.2 (4)
C17^i—C17—H17A	123 (6)	C4—C3—H3	120.4
C12—C17—H17A	117 (6)	C2—C3—H3	120.4
C17^i—C17—H17B	72 (5)	C16—C12—C13	116.3 (5)
C12—C17—H17B	94 (5)	C16—C12—C17	120.3 (5)
H17A—C17—H17B	97 (7)	C13—C12—C17	123.4 (5)
C18—S1—C21	92.4 (3)	C15—C16—C12	120.5 (5)
C20—C21—C21^ii	127.6 (6)	C15—C16—H16	119.7
C20—C21—S1	111.3 (4)	C12—C16—H16	119.7
C21^ii—C21—S1	121.1 (5)	C14—C13—C12	119.8 (5)
C21—C20—C19	111.1 (5)	C14—C13—H13	120.1
C21—C20—H20	124.4	C12—C13—H13	120.1
C19—C20—H20	124.4	N2—C14—C13	123.8 (5)
C18—C19—C20	113.0 (5)	N2—C14—H14	118.1
C18—C19—H19	123.5	C13—C14—H14	118.1
C20—C19—H19	123.5	C1—C7—H7A	109.5
C19—C18—S1	112.2 (4)	C1—C7—H7B	109.5
C19—C18—H18	123.9	H7A—C7—H7B	109.5
S1—C18—H18	123.9	C1—C7—H7C	109.5
C2—O1—H1	109.5	H7A—C7—H7C	109.5
C6—O2—H2	109.5	H7B—C7—H7C	109.5
C3—C4—C5	120.9 (4)	C10—N1—C9	119.1 (4)
C3—C4—H4	119.6	N1—C10—C9^iii	120.4 (4)
C5—C4—H4	119.6	N1—C10—C11	117.9 (4)
O1—C2—C3	121.6 (4)	C9^iii—C10—C11	121.7 (4)
O1—C2—C1	117.2 (4)	N1—C9—C10^iii	120.5 (4)
C3—C2—C1	121.2 (4)	N1—C9—C8	116.7 (4)
C6—C1—C2	118.2 (4)	C10^iii—C9—C8	122.8 (4)
C6—C1—C7	120.4 (4)	C10—C11—H11A	109.5
C2—C1—C7	121.4 (4)	C10—C11—H11B	109.5
C4—C5—C6	119.5 (4)	H11A—C11—H11B	109.5
C4—C5—H5	120.3	C10—C11—H11C	109.5
C6—C5—H5	120.3	H11A—C11—H11C	109.5
C14—N2—C15	116.4 (4)	H11B—C11—H11C	109.5
N2—C15—C16	123.3 (5)	C9—C8—H8A	109.5
N2—C15—H15	118.4	C9—C8—H8B	109.5
C16—C15—H15	118.4	H8A—C8—H8B	109.5
O2—C6—C5	122.0 (4)	C9—C8—H8C	109.5
O2—C6—C1	117.0 (4)	H8A—C8—H8C	109.5
C5—C6—C1	121.0 (4)	H8B—C8—H8C	109.5

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

(MRE_TMP_DPE-II_ACR)

Crystal data

C75H75N8O6	V = 1533.34 (11) Å^3
Mr = 1184.43	Z = 1
Triclinic, P1	F(000) = 629
a = 7.4611 (3) Å	Dx = 1.283 Mg m^−3
b = 8.7285 (4) Å	Mo Kα radiation, λ = 0.71073 Å
c = 23.6219 (10) Å	µ = 0.08 mm^−1
α = 92.850 (1)°	T = 150 K
β = 91.347 (1)°	Block, pale yellow
γ = 93.317 (1)°	0.61 × 0.32 × 0.24 mm

Data collection

Bruker P4 diffractometer	6163 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.023
ω scans	θmax = 27.6°, θmin = 3.2°
Absorption correction: analytical Bruker, AXS, 2006	h = −9→9
Tmin = 0.969, Tmax = 0.981	k = −11→11
39279 measured reflections	l = −30→30
7056 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0472P)^2 + 1.087P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
7056 reflections	Δρmax = 0.37 e Å^−3
434 parameters	Δρmin = −0.28 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
H22A	1.073 (3)	0.599 (2)	0.4582 (8)	0.034 (5)*
H22B	0.987 (2)	0.425 (2)	0.4444 (8)	0.027 (5)*
C1	0.05896 (19)	1.09135 (16)	0.38386 (6)	0.0182 (3)
C2	0.2036 (2)	1.00323 (16)	0.39709 (6)	0.0186 (3)
C3	0.3699 (2)	1.02805 (18)	0.37281 (7)	0.0233 (3)
H3	0.4667	0.9672	0.3823	0.028*
C4	0.3931 (2)	1.14273 (18)	0.33457 (7)	0.0253 (3)
H4	0.5071	1.1610	0.3183	0.030*
C5	0.2525 (2)	1.23083 (18)	0.31985 (7)	0.0247 (3)
H5	0.2693	1.3086	0.2934	0.030*
C6	0.0860 (2)	1.20406 (17)	0.34430 (6)	0.0209 (3)
C7	−0.11880 (19)	1.06719 (18)	0.41171 (6)	0.0217 (3)
H7A	−0.1140	1.1216	0.4491	0.033*
H7B	−0.1448	0.9572	0.4161	0.033*
H7C	−0.2135	1.1071	0.3881	0.033*
C8	0.0808 (2)	1.61215 (18)	0.24794 (7)	0.0258 (3)
C9	0.0887 (2)	1.70944 (18)	0.20271 (7)	0.0251 (3)
C10	−0.0320 (2)	1.51123 (18)	0.14223 (7)	0.0249 (3)
C11	−0.0388 (2)	1.41367 (18)	0.18738 (7)	0.0254 (3)
C12	0.1431 (3)	1.6651 (2)	0.30693 (8)	0.0387 (4)
H12A	0.1101	1.5854	0.3332	0.058*
H12B	0.0861	1.7599	0.3181	0.058*
H12C	0.2739	1.6845	0.3079	0.058*
C13	0.1584 (3)	1.87401 (19)	0.21062 (9)	0.0378 (4)
H13A	0.1631	1.9203	0.1737	0.057*
H13B	0.2792	1.8787	0.2280	0.057*
H13C	0.0783	1.9304	0.2353	0.057*
C14	−0.0966 (3)	1.4577 (2)	0.08351 (7)	0.0366 (4)
H14A	−0.0728	1.5400	0.0575	0.055*
H14B	−0.2260	1.4309	0.0836	0.055*
H14C	−0.0333	1.3672	0.0711	0.055*
C15	−0.1078 (3)	1.24893 (19)	0.18044 (9)	0.0385 (4)
H15A	−0.0831	1.1970	0.2154	0.058*
H15B	−0.0479	1.1981	0.1488	0.058*
H15C	−0.2377	1.2440	0.1726	0.058*
C17	0.5907 (2)	0.77840 (18)	0.47965 (7)	0.0245 (3)
H17	0.5697	0.8763	0.4968	0.029*
C18	0.7589 (2)	0.72284 (17)	0.48693 (7)	0.0239 (3)
H18	0.8502	0.7822	0.5082	0.029*
C19	0.7935 (2)	0.57950 (17)	0.46291 (6)	0.0201 (3)
C20	0.6520 (2)	0.49820 (17)	0.43325 (6)	0.0220 (3)
H20	0.6679	0.3985	0.4168	0.026*
C21	0.4878 (2)	0.56340 (17)	0.42775 (6)	0.0226 (3)
H21	0.3934	0.5061	0.4071	0.027*
C22	0.9776 (2)	0.51781 (19)	0.46924 (6)	0.0234 (3)
N1	0.45545 (17)	0.70285 (15)	0.44996 (5)	0.0224 (3)
N2	0.0155 (2)	1.46641 (15)	0.23955 (6)	0.0272 (3)
N3	0.03111 (19)	1.65743 (15)	0.15070 (6)	0.0262 (3)
O1	0.17253 (14)	0.89257 (12)	0.43525 (5)	0.0238 (2)
H1	0.2591	0.8353	0.4358	0.036*
O2	−0.05784 (16)	1.28662 (14)	0.33110 (5)	0.0295 (3)
H2	−0.0331	1.3407	0.3036	0.044*
C23	0.5759 (2)	0.5921 (2)	0.23328 (7)	0.0343 (4)
C24	0.6406 (3)	0.6229 (3)	0.29041 (8)	0.0488 (5)
H24	0.6375	0.5424	0.3161	0.059*
C25	0.7055 (3)	0.7639 (3)	0.30811 (10)	0.0548 (6)
H25	0.7465	0.7828	0.3463	0.066*
C26	0.7134 (3)	0.8842 (3)	0.27056 (10)	0.0514 (6)
H26	0.7587	0.9838	0.2839	0.062*
C27	0.6568 (3)	0.8600 (2)	0.21509 (10)	0.0446 (5)
H27	0.6659	0.9420	0.1901	0.054*
C28	0.5842 (2)	0.7118 (2)	0.19454 (8)	0.0333 (4)
C29	0.5205 (2)	0.6776 (2)	0.13933 (8)	0.0339 (4)
H29	0.5228	0.7553	0.1125	0.041*
C30	0.4533 (2)	0.5295 (2)	0.12335 (7)	0.0324 (4)
C31	0.3917 (3)	0.4845 (3)	0.06710 (8)	0.0450 (5)
H31	0.3913	0.5584	0.0389	0.054*
C32	0.3338 (3)	0.3374 (3)	0.05361 (10)	0.0587 (7)
H32	0.2964	0.3083	0.0157	0.070*
C33	0.3284 (4)	0.2270 (3)	0.09495 (11)	0.0646 (8)
H33	0.2857	0.1245	0.0847	0.077*
C34	0.3831 (3)	0.2647 (2)	0.14931 (10)	0.0516 (6)
H34	0.3768	0.1891	0.1769	0.062*
C35	0.4501 (2)	0.4177 (2)	0.16524 (8)	0.0335 (4)
N4	0.5096 (2)	0.44878 (19)	0.21887 (6)	0.0380 (4)
C36	0.3269 (4)	0.9247 (4)	−0.03392 (14)	0.0263 (6)	0.5
H36A	0.4127	1.0092	−0.0210	0.039*	0.5
H36B	0.3298	0.9105	−0.0753	0.039*	0.5
H36C	0.3593	0.8300	−0.0167	0.039*	0.5
C37	0.1664 (3)	0.9572 (2)	−0.01907 (9)	0.0451 (5)
C38	0.0928 (3)	0.8914 (2)	0.02825 (9)	0.0498 (6)
C39	−0.0723 (3)	0.9334 (2)	0.04711 (9)	0.0497 (6)
O3	−0.1319 (3)	0.8653 (3)	0.08669 (10)	0.0319 (5)	0.5
H3A	−0.0514	0.8146	0.1009	0.048*	0.5
O4	0.1701 (4)	0.7986 (3)	0.05950 (11)	0.0371 (6)	0.5
H4A	0.0985	0.7674	0.0839	0.056*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0208 (7)	0.0180 (7)	0.0156 (6)	0.0024 (5)	−0.0013 (5)	−0.0014 (5)
C2	0.0229 (7)	0.0178 (6)	0.0152 (6)	0.0025 (5)	−0.0006 (5)	0.0007 (5)
C3	0.0216 (7)	0.0246 (7)	0.0248 (8)	0.0081 (6)	0.0011 (6)	0.0035 (6)
C4	0.0241 (8)	0.0266 (8)	0.0257 (8)	0.0024 (6)	0.0067 (6)	0.0031 (6)
C5	0.0316 (8)	0.0211 (7)	0.0222 (7)	0.0031 (6)	0.0036 (6)	0.0053 (6)
C6	0.0254 (7)	0.0197 (7)	0.0181 (7)	0.0059 (6)	−0.0016 (6)	0.0010 (5)
C7	0.0182 (7)	0.0250 (7)	0.0219 (7)	0.0024 (6)	−0.0013 (5)	0.0016 (6)
C8	0.0294 (8)	0.0223 (7)	0.0256 (8)	0.0058 (6)	−0.0057 (6)	−0.0019 (6)
C9	0.0244 (8)	0.0197 (7)	0.0313 (8)	0.0030 (6)	−0.0012 (6)	0.0008 (6)
C10	0.0278 (8)	0.0244 (8)	0.0226 (7)	0.0056 (6)	−0.0017 (6)	0.0001 (6)
C11	0.0307 (8)	0.0192 (7)	0.0262 (8)	0.0031 (6)	−0.0026 (6)	−0.0002 (6)
C12	0.0463 (11)	0.0376 (10)	0.0311 (9)	0.0069 (8)	−0.0144 (8)	−0.0071 (7)
C13	0.0358 (10)	0.0208 (8)	0.0564 (12)	−0.0007 (7)	0.0017 (8)	−0.0004 (8)
C14	0.0438 (10)	0.0421 (10)	0.0233 (8)	0.0052 (8)	−0.0052 (7)	−0.0032 (7)
C15	0.0526 (12)	0.0199 (8)	0.0420 (10)	−0.0011 (8)	−0.0023 (9)	−0.0018 (7)
C17	0.0278 (8)	0.0191 (7)	0.0272 (8)	0.0075 (6)	−0.0019 (6)	0.0006 (6)
C18	0.0239 (7)	0.0207 (7)	0.0269 (8)	0.0025 (6)	−0.0064 (6)	−0.0005 (6)
C19	0.0219 (7)	0.0218 (7)	0.0174 (7)	0.0055 (6)	−0.0011 (5)	0.0045 (5)
C20	0.0272 (8)	0.0198 (7)	0.0193 (7)	0.0055 (6)	−0.0024 (6)	0.0005 (5)
C21	0.0232 (7)	0.0235 (7)	0.0211 (7)	0.0006 (6)	−0.0036 (6)	0.0027 (6)
C22	0.0221 (7)	0.0263 (8)	0.0227 (8)	0.0083 (6)	−0.0017 (6)	0.0017 (6)
N1	0.0214 (6)	0.0233 (6)	0.0234 (6)	0.0061 (5)	−0.0002 (5)	0.0063 (5)
N2	0.0369 (8)	0.0206 (6)	0.0244 (7)	0.0048 (6)	−0.0045 (6)	0.0034 (5)
N3	0.0304 (7)	0.0235 (7)	0.0256 (7)	0.0039 (5)	0.0006 (5)	0.0060 (5)
O1	0.0223 (5)	0.0251 (6)	0.0258 (6)	0.0080 (4)	0.0033 (4)	0.0096 (4)
O2	0.0312 (6)	0.0318 (6)	0.0282 (6)	0.0127 (5)	0.0026 (5)	0.0134 (5)
C23	0.0313 (9)	0.0426 (10)	0.0277 (9)	−0.0038 (7)	0.0110 (7)	−0.0104 (7)
C24	0.0458 (12)	0.0707 (15)	0.0283 (10)	0.0009 (10)	0.0092 (8)	−0.0136 (9)
C25	0.0423 (12)	0.0776 (17)	0.0411 (12)	−0.0017 (11)	0.0082 (9)	−0.0298 (12)
C26	0.0315 (10)	0.0510 (12)	0.0670 (15)	−0.0051 (9)	0.0097 (9)	−0.0402 (12)
C27	0.0332 (10)	0.0338 (10)	0.0651 (14)	−0.0047 (8)	0.0157 (9)	−0.0133 (9)
C28	0.0259 (8)	0.0308 (9)	0.0417 (10)	−0.0039 (7)	0.0123 (7)	−0.0102 (7)
C29	0.0324 (9)	0.0313 (9)	0.0386 (10)	0.0014 (7)	0.0108 (7)	0.0044 (7)
C30	0.0284 (8)	0.0395 (10)	0.0284 (8)	−0.0031 (7)	0.0068 (7)	−0.0050 (7)
C31	0.0384 (10)	0.0641 (14)	0.0310 (10)	−0.0007 (9)	0.0012 (8)	−0.0076 (9)
C32	0.0485 (13)	0.0816 (18)	0.0405 (12)	−0.0161 (12)	0.0013 (10)	−0.0271 (12)
C33	0.0655 (16)	0.0561 (14)	0.0649 (16)	−0.0325 (12)	0.0194 (12)	−0.0351 (12)
C34	0.0624 (14)	0.0364 (11)	0.0526 (13)	−0.0211 (10)	0.0189 (11)	−0.0104 (9)
C35	0.0358 (9)	0.0320 (9)	0.0310 (9)	−0.0097 (7)	0.0113 (7)	−0.0065 (7)
N4	0.0455 (9)	0.0389 (9)	0.0286 (8)	−0.0077 (7)	0.0125 (7)	−0.0015 (6)
C36	0.0249 (16)	0.0274 (16)	0.0276 (16)	0.0055 (12)	0.0070 (12)	0.0033 (12)
C37	0.0585 (13)	0.0294 (9)	0.0447 (11)	−0.0161 (9)	−0.0246 (10)	0.0079 (8)
C38	0.0661 (15)	0.0324 (10)	0.0483 (12)	−0.0183 (10)	−0.0303 (11)	0.0155 (9)
C39	0.0681 (15)	0.0315 (10)	0.0465 (12)	−0.0203 (10)	−0.0301 (11)	0.0141 (9)
O3	0.0363 (13)	0.0364 (13)	0.0256 (12)	0.0095 (10)	0.0068 (10)	0.0162 (10)
O4	0.0410 (14)	0.0374 (14)	0.0358 (14)	0.0091 (11)	0.0083 (11)	0.0203 (11)

Geometric parameters (Å, º)

C1—C2	1.399 (2)	C20—H20	0.9500
C1—C6	1.400 (2)	C21—N1	1.339 (2)
C1—C7	1.503 (2)	C21—H21	0.9500
C2—O1	1.3675 (17)	C22—C22^i	1.534 (3)
C2—C3	1.389 (2)	C22—H22A	1.02 (2)
C3—C4	1.387 (2)	C22—H22B	0.98 (2)
C3—H3	0.9500	O1—H1	0.8400
C4—C5	1.384 (2)	O2—H2	0.8400
C4—H4	0.9500	C23—N4	1.343 (2)
C5—C6	1.395 (2)	C23—C28	1.423 (3)
C5—H5	0.9500	C23—C24	1.430 (3)
C6—O2	1.3656 (18)	C24—C25	1.340 (3)
C7—H7A	0.9800	C24—H24	0.9500
C7—H7B	0.9800	C25—C26	1.408 (4)
C7—H7C	0.9800	C25—H25	0.9500
C8—N2	1.339 (2)	C26—C27	1.370 (3)
C8—C9	1.398 (2)	C26—H26	0.9500
C8—C12	1.501 (2)	C27—C28	1.431 (2)
C9—N3	1.341 (2)	C27—H27	0.9500
C9—C13	1.500 (2)	C28—C29	1.390 (3)
C10—N3	1.338 (2)	C29—C30	1.390 (3)
C10—C11	1.397 (2)	C29—H29	0.9500
C10—C14	1.501 (2)	C30—C35	1.424 (3)
C11—N2	1.339 (2)	C30—C31	1.425 (3)
C11—C15	1.499 (2)	C31—C32	1.351 (3)
C12—H12A	0.9800	C31—H31	0.9500
C12—H12B	0.9800	C32—C33	1.405 (4)
C12—H12C	0.9800	C32—H32	0.9500
C13—H13A	0.9800	C33—C34	1.357 (3)
C13—H13B	0.9800	C33—H33	0.9500
C13—H13C	0.9800	C34—C35	1.427 (3)
C14—H14A	0.9800	C34—H34	0.9500
C14—H14B	0.9800	C35—N4	1.342 (2)
C14—H14C	0.9800	C36—C37	1.299 (4)
C15—H15A	0.9800	C36—H36A	0.9800
C15—H15B	0.9800	C36—H36B	0.9800
C15—H15C	0.9800	C36—H36C	0.9800
C17—N1	1.337 (2)	C37—C38	1.392 (3)
C17—C18	1.382 (2)	C37—C39^ii	1.401 (3)
C17—H17	0.9500	C38—O4	1.276 (3)
C18—C19	1.388 (2)	C38—C39	1.383 (4)
C18—H18	0.9500	C39—O3	1.212 (3)
C19—C20	1.392 (2)	C39—C37^ii	1.401 (3)
C19—C22	1.511 (2)	O3—H3A	0.8400
C20—C21	1.386 (2)	O4—H4A	0.8400
C2—C1—C6	117.75 (13)	N1—C21—C20	123.43 (14)
C2—C1—C7	121.15 (13)	N1—C21—H21	118.3
C6—C1—C7	121.09 (13)	C20—C21—H21	118.3
O1—C2—C3	122.04 (13)	C19—C22—C22^i	112.07 (16)
O1—C2—C1	116.47 (13)	C19—C22—H22A	109.7 (11)
C3—C2—C1	121.48 (13)	C22^i—C22—H22A	106.2 (11)
C4—C3—C2	119.26 (14)	C19—C22—H22B	110.5 (11)
C4—C3—H3	120.4	C22^i—C22—H22B	109.7 (11)
C2—C3—H3	120.4	H22A—C22—H22B	108.5 (16)
C5—C4—C3	120.92 (15)	C17—N1—C21	116.44 (13)
C5—C4—H4	119.5	C11—N2—C8	119.61 (14)
C3—C4—H4	119.5	C10—N3—C9	119.56 (13)
C4—C5—C6	119.19 (14)	C2—O1—H1	109.5
C4—C5—H5	120.4	C6—O2—H2	109.5
C6—C5—H5	120.4	N4—C23—C28	123.03 (16)
O2—C6—C5	121.79 (13)	N4—C23—C24	117.41 (19)
O2—C6—C1	116.83 (13)	C28—C23—C24	119.56 (18)
C5—C6—C1	121.37 (14)	C25—C24—C23	120.7 (2)
C1—C7—H7A	109.5	C25—C24—H24	119.6
C1—C7—H7B	109.5	C23—C24—H24	119.6
H7A—C7—H7B	109.5	C24—C25—C26	120.6 (2)
C1—C7—H7C	109.5	C24—C25—H25	119.7
H7A—C7—H7C	109.5	C26—C25—H25	119.7
H7B—C7—H7C	109.5	C27—C26—C25	121.02 (19)
N2—C8—C9	120.15 (14)	C27—C26—H26	119.5
N2—C8—C12	117.65 (15)	C25—C26—H26	119.5
C9—C8—C12	122.21 (15)	C26—C27—C28	120.3 (2)
N3—C9—C8	120.22 (14)	C26—C27—H27	119.8
N3—C9—C13	118.08 (15)	C28—C27—H27	119.8
C8—C9—C13	121.69 (15)	C29—C28—C23	118.00 (16)
N3—C10—C11	120.21 (14)	C29—C28—C27	124.23 (19)
N3—C10—C14	117.97 (15)	C23—C28—C27	117.77 (18)
C11—C10—C14	121.82 (15)	C28—C29—C30	119.89 (17)
N2—C11—C10	120.23 (14)	C28—C29—H29	120.1
N2—C11—C15	117.19 (15)	C30—C29—H29	120.1
C10—C11—C15	122.57 (15)	C29—C30—C35	117.93 (16)
C8—C12—H12A	109.5	C29—C30—C31	123.10 (19)
C8—C12—H12B	109.5	C35—C30—C31	118.96 (17)
H12A—C12—H12B	109.5	C32—C31—C30	120.4 (2)
C8—C12—H12C	109.5	C32—C31—H31	119.8
H12A—C12—H12C	109.5	C30—C31—H31	119.8
H12B—C12—H12C	109.5	C31—C32—C33	120.8 (2)
C9—C13—H13A	109.5	C31—C32—H32	119.6
C9—C13—H13B	109.5	C33—C32—H32	119.6
H13A—C13—H13B	109.5	C34—C33—C32	120.9 (2)
C9—C13—H13C	109.5	C34—C33—H33	119.5
H13A—C13—H13C	109.5	C32—C33—H33	119.5
H13B—C13—H13C	109.5	C33—C34—C35	120.2 (2)
C10—C14—H14A	109.5	C33—C34—H34	119.9
C10—C14—H14B	109.5	C35—C34—H34	119.9
H14A—C14—H14B	109.5	N4—C35—C30	123.05 (16)
C10—C14—H14C	109.5	N4—C35—C34	118.38 (18)
H14A—C14—H14C	109.5	C30—C35—C34	118.56 (18)
H14B—C14—H14C	109.5	C23—N4—C35	118.09 (16)
C11—C15—H15A	109.5	C37—C36—H36A	109.5
C11—C15—H15B	109.5	C37—C36—H36B	109.5
H15A—C15—H15B	109.5	H36A—C36—H36B	109.5
C11—C15—H15C	109.5	C37—C36—H36C	109.5
H15A—C15—H15C	109.5	H36A—C36—H36C	109.5
H15B—C15—H15C	109.5	H36B—C36—H36C	109.5
N1—C17—C18	124.03 (14)	C36—C37—C38	119.4 (2)
N1—C17—H17	118.0	C36—C37—C39^ii	121.0 (2)
C18—C17—H17	118.0	C38—C37—C39^ii	119.5 (2)
C17—C18—C19	119.47 (14)	O4—C38—C39	114.4 (2)
C17—C18—H18	120.3	O4—C38—C37	125.4 (3)
C19—C18—H18	120.3	C39—C38—C37	120.11 (19)
C18—C19—C20	116.88 (14)	O3—C39—C38	116.3 (2)
C18—C19—C22	120.42 (14)	O3—C39—C37^ii	123.2 (3)
C20—C19—C22	122.70 (14)	C38—C39—C37^ii	120.4 (2)
C21—C20—C19	119.71 (14)	C39—O3—H3A	109.5
C21—C20—H20	120.1	C38—O4—H4A	109.5
C19—C20—H20	120.1
C6—C1—C2—O1	−179.10 (12)	C13—C9—N3—C10	−179.93 (15)
C7—C1—C2—O1	1.6 (2)	N4—C23—C24—C25	−178.74 (19)
C6—C1—C2—C3	1.2 (2)	C28—C23—C24—C25	1.4 (3)
C7—C1—C2—C3	−178.01 (14)	C23—C24—C25—C26	−0.8 (3)
O1—C2—C3—C4	−179.66 (14)	C24—C25—C26—C27	−0.6 (3)
C1—C2—C3—C4	0.0 (2)	C25—C26—C27—C28	1.5 (3)
C2—C3—C4—C5	−0.9 (2)	N4—C23—C28—C29	0.0 (3)
C3—C4—C5—C6	0.5 (2)	C24—C23—C28—C29	179.84 (17)
C4—C5—C6—O2	−179.54 (14)	N4—C23—C28—C27	179.64 (17)
C4—C5—C6—C1	0.8 (2)	C24—C23—C28—C27	−0.5 (3)
C2—C1—C6—O2	178.68 (13)	C26—C27—C28—C29	178.72 (18)
C7—C1—C6—O2	−2.1 (2)	C26—C27—C28—C23	−0.9 (3)
C2—C1—C6—C5	−1.6 (2)	C23—C28—C29—C30	−0.7 (3)
C7—C1—C6—C5	177.63 (14)	C27—C28—C29—C30	179.61 (17)
N2—C8—C9—N3	−0.1 (2)	C28—C29—C30—C35	1.0 (3)
C12—C8—C9—N3	−179.85 (16)	C28—C29—C30—C31	−177.69 (17)
N2—C8—C9—C13	179.08 (15)	C29—C30—C31—C32	177.6 (2)
C12—C8—C9—C13	−0.7 (3)	C35—C30—C31—C32	−1.0 (3)
N3—C10—C11—N2	1.0 (2)	C30—C31—C32—C33	1.8 (4)
C14—C10—C11—N2	−178.18 (16)	C31—C32—C33—C34	−0.8 (4)
N3—C10—C11—C15	−179.90 (16)	C32—C33—C34—C35	−1.0 (4)
C14—C10—C11—C15	1.0 (3)	C29—C30—C35—N4	−0.4 (3)
N1—C17—C18—C19	−0.6 (3)	C31—C30—C35—N4	178.28 (18)
C17—C18—C19—C20	−1.1 (2)	C29—C30—C35—C34	−179.39 (18)
C17—C18—C19—C22	178.68 (14)	C31—C30—C35—C34	−0.7 (3)
C18—C19—C20—C21	1.6 (2)	C33—C34—C35—N4	−177.3 (2)
C22—C19—C20—C21	−178.22 (14)	C33—C34—C35—C30	1.7 (3)
C19—C20—C21—N1	−0.4 (2)	C28—C23—N4—C35	0.6 (3)
C18—C19—C22—C22^i	67.6 (2)	C24—C23—N4—C35	−179.31 (17)
C20—C19—C22—C22^i	−112.58 (19)	C30—C35—N4—C23	−0.3 (3)
C18—C17—N1—C21	1.9 (2)	C34—C35—N4—C23	178.64 (18)
C20—C21—N1—C17	−1.4 (2)	C36—C37—C38—O4	−0.3 (4)
C10—C11—N2—C8	−1.8 (2)	C39^ii—C37—C38—O4	−175.1 (2)
C15—C11—N2—C8	179.04 (16)	C36—C37—C38—C39	175.2 (2)
C9—C8—N2—C11	1.3 (2)	C39^ii—C37—C38—C39	0.4 (3)
C12—C8—N2—C11	−178.86 (16)	O4—C38—C39—O3	−7.8 (3)
C11—C10—N3—C9	0.3 (2)	C37—C38—C39—O3	176.2 (2)
C14—C10—N3—C9	179.50 (15)	O4—C38—C39—C37^ii	175.6 (2)
C8—C9—N3—C10	−0.8 (2)	C37—C38—C39—C37^ii	−0.4 (3)

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

(MRE_TMP_DPE-II_ACR_TMBQ)

Crystal data

C77H79N8O5	V = 1537.18 (10) Å^3
Mr = 1196.48	Z = 1
Triclinic, P1	F(000) = 637
a = 7.4709 (3) Å	Dx = 1.292 Mg m^−3
b = 8.7326 (3) Å	Mo Kα radiation, λ = 0.71073 Å
c = 23.6381 (9) Å	µ = 0.08 mm^−1
α = 92.857 (1)°	T = 293 K
β = 91.317 (1)°	Block, brown
γ = 93.293 (1)°	0.53 × 0.18 × 0.16 mm

Data collection

CCD area detector diffractometer	5177 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.048
phi and ω scans	θmax = 27.6°, θmin = 3.2°
Absorption correction: analytical Bruker, AXS, 2008	h = −9→9
Tmin = 0.982, Tmax = 0.987	k = −11→11
80029 measured reflections	l = −30→30
7136 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.164	w = 1/[σ^2(Fo^2) + (0.0749P)^2 + 1.0559P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.048
7136 reflections	Δρmax = 0.42 e Å^−3
432 parameters	Δρmin = −0.44 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.4136 (2)	−0.2033 (2)	0.15567 (7)	0.0218 (4)
C2	0.4408 (2)	−0.09129 (19)	0.11618 (7)	0.0188 (4)
C3	0.2959 (2)	−0.00301 (19)	0.10292 (7)	0.0200 (4)
C4	0.1301 (2)	−0.0283 (2)	0.12717 (8)	0.0244 (4)
H4	0.0354	0.0311	0.1179	0.029*
C5	0.1069 (3)	−0.1426 (2)	0.16528 (8)	0.0267 (4)
H5	−0.0046	−0.1606	0.1812	0.032*
C6	0.2473 (3)	−0.2305 (2)	0.18011 (8)	0.0263 (4)
H6	0.2311	−0.3066	0.2060	0.032*
C7	0.6180 (2)	−0.0669 (2)	0.08829 (8)	0.0236 (4)
H7A	0.7108	−0.1058	0.1114	0.035*
H7B	0.6431	0.0408	0.0839	0.035*
H7C	0.6134	−0.1203	0.0517	0.035*
C8	0.4194 (3)	−0.6116 (2)	0.25193 (8)	0.0269 (4)
C9	0.4114 (3)	−0.7095 (2)	0.29709 (8)	0.0265 (4)
C10	0.5317 (3)	−0.5116 (2)	0.35761 (8)	0.0259 (4)
C11	0.5385 (3)	−0.4139 (2)	0.31252 (8)	0.0267 (4)
C12	0.3575 (3)	−0.6645 (3)	0.19299 (9)	0.0398 (5)
H12A	0.2298	−0.6850	0.1921	0.060*
H12B	0.4147	−0.7565	0.1818	0.060*
H12C	0.3882	−0.5859	0.1673	0.060*
C13	0.3415 (3)	−0.8737 (2)	0.28909 (11)	0.0391 (5)
H13A	0.3359	−0.9190	0.3252	0.059*
H13B	0.4202	−0.9292	0.2652	0.059*
H13C	0.2237	−0.8782	0.2718	0.059*
C14	0.5969 (3)	−0.4588 (3)	0.41629 (9)	0.0383 (5)
H14A	0.5750	−0.5400	0.4416	0.057*
H14B	0.5343	−0.3708	0.4288	0.057*
H14C	0.7232	−0.4316	0.4160	0.057*
C15	0.6072 (3)	−0.2491 (2)	0.31952 (10)	0.0403 (5)
H15A	0.5836	−0.1983	0.2853	0.060*
H15B	0.7341	−0.2442	0.3274	0.060*
H15C	0.5480	−0.1993	0.3504	0.060*
C16	−0.0911 (3)	0.2215 (2)	0.02037 (8)	0.0259 (4)
H16	−0.0710	0.1255	0.0037	0.031*
C17	−0.2588 (3)	0.2775 (2)	0.01301 (8)	0.0256 (4)
H17	−0.3478	0.2196	−0.0079	0.031*
C18	−0.2937 (2)	0.4205 (2)	0.03697 (7)	0.0210 (4)
C19	−0.1526 (2)	0.5016 (2)	0.06670 (7)	0.0234 (4)
H19	−0.1682	0.5991	0.0828	0.028*
C20	0.0116 (2)	0.4363 (2)	0.07224 (7)	0.0237 (4)
H20	0.1039	0.4923	0.0924	0.028*
C21	−0.4776 (3)	0.4823 (2)	0.03062 (8)	0.0256 (4)
C22	−0.0755 (3)	0.4077 (3)	0.26691 (9)	0.0361 (5)
C23	−0.1404 (3)	0.3765 (3)	0.20982 (10)	0.0521 (7)
H23	−0.1375	0.4551	0.1847	0.062*
C24	−0.2054 (4)	0.2358 (4)	0.19211 (12)	0.0575 (8)
H24	−0.2456	0.2173	0.1547	0.069*
C25	−0.2131 (3)	0.1164 (3)	0.22942 (12)	0.0543 (8)
H25	−0.2572	0.0190	0.2163	0.065*
C26	−0.1569 (3)	0.1402 (3)	0.28511 (12)	0.0471 (6)
H26	−0.1661	0.0600	0.3095	0.057*
C27	−0.0841 (3)	0.2887 (2)	0.30550 (9)	0.0346 (5)
C28	−0.0203 (3)	0.3228 (2)	0.36069 (9)	0.0355 (5)
H28	−0.0230	0.2468	0.3869	0.043*
C29	0.0473 (3)	0.4704 (2)	0.37670 (9)	0.0339 (5)
C30	0.1087 (3)	0.5158 (3)	0.43279 (10)	0.0468 (6)
H30	0.1092	0.4436	0.4604	0.056*
C31	0.1663 (4)	0.6630 (4)	0.44620 (12)	0.0597 (8)
H31	0.2025	0.6917	0.4833	0.072*
C32	0.1721 (4)	0.7733 (3)	0.40475 (13)	0.0655 (9)
H32	0.2144	0.8735	0.4146	0.079*
C33	0.1167 (4)	0.7353 (3)	0.35053 (12)	0.0529 (7)
H33	0.1222	0.8093	0.3236	0.064*
C34	0.0501 (3)	0.5827 (2)	0.33467 (9)	0.0354 (5)
C35	0.3356 (4)	0.0422 (3)	0.51899 (11)	0.0461 (6)
C36	0.4070 (4)	0.1084 (3)	0.47180 (11)	0.0530 (7)
C37	0.5725 (4)	0.0665 (3)	0.45300 (11)	0.0529 (7)
C38	0.6294 (4)	0.1338 (3)	0.41311 (12)	0.0317 (6)	0.7196
H38A	0.5356	0.1893	0.3967	0.048*	0.7196
H38B	0.6709	0.0612	0.3853	0.048*	0.7196
H38C	0.7271	0.2045	0.4257	0.048*	0.7196
C39	0.3322 (4)	0.1998 (3)	0.44067 (12)	0.0407 (7)	0.7807
H39A	0.2948	0.2856	0.4635	0.061*	0.7807
H39B	0.2295	0.1479	0.4216	0.061*	0.7807
H39C	0.4153	0.2356	0.4132	0.061*	0.7807
N1	0.4842 (2)	−0.46644 (18)	0.26035 (7)	0.0280 (4)
N2	0.4689 (2)	−0.65755 (18)	0.34903 (7)	0.0279 (4)
N3	0.0439 (2)	0.29676 (17)	0.05003 (6)	0.0233 (3)
N4	−0.0097 (3)	0.5511 (2)	0.28124 (8)	0.0400 (5)
O1	0.55755 (18)	−0.28582 (16)	0.16893 (6)	0.0310 (3)
H1	0.5325	−0.3403	0.1952	0.047*
O2	0.32700 (17)	0.10732 (14)	0.06473 (5)	0.0251 (3)
H2	0.2400	0.1601	0.0628	0.038*
O3	0.1750 (6)	0.0753 (5)	0.53408 (18)	0.0650 (10)	0.5
H21A	−0.575 (3)	0.399 (3)	0.0414 (9)	0.037 (6)*
H21B	−0.485 (3)	0.577 (3)	0.0543 (9)	0.031 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0262 (9)	0.0200 (8)	0.0196 (8)	0.0061 (7)	−0.0024 (7)	0.0004 (7)
C2	0.0206 (8)	0.0191 (8)	0.0164 (8)	0.0019 (7)	−0.0014 (6)	−0.0018 (6)
C3	0.0251 (9)	0.0187 (8)	0.0161 (8)	0.0030 (7)	−0.0019 (7)	0.0004 (6)
C4	0.0225 (9)	0.0256 (9)	0.0259 (9)	0.0079 (7)	0.0009 (7)	0.0034 (7)
C5	0.0250 (10)	0.0290 (10)	0.0268 (10)	0.0024 (8)	0.0059 (8)	0.0033 (8)
C6	0.0338 (10)	0.0225 (9)	0.0236 (9)	0.0036 (8)	0.0045 (8)	0.0072 (7)
C7	0.0215 (9)	0.0267 (9)	0.0224 (9)	0.0010 (7)	−0.0030 (7)	0.0022 (7)
C8	0.0290 (10)	0.0226 (9)	0.0290 (10)	0.0059 (7)	−0.0062 (8)	−0.0013 (7)
C9	0.0258 (9)	0.0209 (9)	0.0328 (10)	0.0031 (7)	−0.0017 (8)	0.0006 (8)
C10	0.0282 (10)	0.0252 (9)	0.0243 (9)	0.0043 (8)	−0.0027 (7)	0.0000 (7)
C11	0.0325 (10)	0.0205 (9)	0.0269 (10)	0.0034 (8)	−0.0031 (8)	−0.0004 (7)
C12	0.0474 (13)	0.0397 (12)	0.0312 (11)	0.0067 (10)	−0.0135 (10)	−0.0064 (9)
C13	0.0380 (12)	0.0223 (10)	0.0566 (14)	−0.0008 (9)	0.0018 (10)	0.0000 (9)
C14	0.0451 (13)	0.0448 (13)	0.0245 (10)	0.0044 (10)	−0.0049 (9)	−0.0036 (9)
C15	0.0544 (14)	0.0215 (10)	0.0440 (13)	−0.0007 (9)	−0.0024 (11)	−0.0020 (9)
C16	0.0299 (10)	0.0201 (9)	0.0281 (10)	0.0073 (7)	−0.0022 (8)	0.0007 (7)
C17	0.0260 (10)	0.0215 (9)	0.0290 (10)	0.0023 (7)	−0.0066 (8)	0.0003 (7)
C18	0.0225 (9)	0.0233 (9)	0.0180 (8)	0.0066 (7)	−0.0019 (7)	0.0046 (7)
C19	0.0289 (10)	0.0205 (9)	0.0208 (9)	0.0058 (7)	−0.0039 (7)	−0.0004 (7)
C20	0.0241 (9)	0.0252 (9)	0.0215 (9)	0.0002 (7)	−0.0049 (7)	0.0033 (7)
C21	0.0254 (10)	0.0292 (10)	0.0231 (10)	0.0099 (8)	−0.0034 (7)	0.0022 (8)
C22	0.0312 (11)	0.0458 (13)	0.0299 (11)	−0.0040 (9)	0.0117 (9)	−0.0103 (9)
C23	0.0488 (15)	0.0742 (18)	0.0314 (12)	−0.0006 (13)	0.0102 (10)	−0.0144 (12)
C24	0.0463 (15)	0.080 (2)	0.0430 (14)	−0.0021 (14)	0.0094 (11)	−0.0296 (14)
C25	0.0351 (13)	0.0524 (15)	0.0703 (18)	−0.0052 (11)	0.0085 (12)	−0.0422 (14)
C26	0.0359 (13)	0.0354 (12)	0.0684 (17)	−0.0047 (10)	0.0168 (11)	−0.0126 (11)
C27	0.0262 (10)	0.0325 (11)	0.0435 (12)	−0.0037 (8)	0.0121 (9)	−0.0114 (9)
C28	0.0340 (11)	0.0329 (11)	0.0403 (12)	0.0001 (9)	0.0118 (9)	0.0044 (9)
C29	0.0304 (11)	0.0404 (12)	0.0298 (10)	−0.0027 (9)	0.0067 (8)	−0.0072 (9)
C30	0.0405 (13)	0.0655 (17)	0.0334 (12)	0.0031 (11)	0.0000 (10)	−0.0082 (11)
C31	0.0467 (15)	0.083 (2)	0.0442 (15)	−0.0110 (14)	0.0002 (12)	−0.0298 (15)
C32	0.0641 (18)	0.0555 (17)	0.0698 (19)	−0.0310 (14)	0.0152 (15)	−0.0342 (15)
C33	0.0627 (17)	0.0384 (13)	0.0544 (15)	−0.0206 (12)	0.0193 (13)	−0.0103 (11)
C34	0.0368 (12)	0.0346 (11)	0.0331 (11)	−0.0093 (9)	0.0121 (9)	−0.0074 (9)
C35	0.0546 (15)	0.0326 (12)	0.0487 (14)	−0.0135 (11)	−0.0221 (12)	0.0069 (10)
C36	0.0740 (19)	0.0341 (12)	0.0480 (14)	−0.0215 (12)	−0.0330 (13)	0.0169 (11)
C37	0.0736 (19)	0.0335 (12)	0.0482 (14)	−0.0222 (12)	−0.0314 (13)	0.0142 (11)
C38	0.0357 (15)	0.0338 (15)	0.0275 (14)	0.0060 (12)	0.0055 (12)	0.0119 (12)
C39	0.0448 (17)	0.0390 (16)	0.0403 (16)	0.0069 (13)	0.0070 (13)	0.0145 (13)
N1	0.0377 (9)	0.0217 (8)	0.0250 (8)	0.0056 (7)	−0.0040 (7)	0.0038 (6)
N2	0.0328 (9)	0.0246 (8)	0.0272 (8)	0.0040 (7)	0.0009 (7)	0.0064 (6)
N3	0.0230 (8)	0.0243 (8)	0.0237 (8)	0.0068 (6)	−0.0013 (6)	0.0072 (6)
N4	0.0464 (11)	0.0409 (10)	0.0316 (10)	−0.0076 (9)	0.0127 (8)	−0.0021 (8)
O1	0.0322 (8)	0.0337 (8)	0.0299 (7)	0.0131 (6)	0.0030 (6)	0.0148 (6)
O2	0.0243 (7)	0.0263 (7)	0.0266 (7)	0.0085 (5)	0.0034 (5)	0.0105 (5)
O3	0.064 (3)	0.064 (3)	0.069 (3)	0.010 (2)	0.011 (2)	0.005 (2)

Geometric parameters (Å, º)

C1—O1	1.368 (2)	C20—N3	1.340 (2)
C1—C6	1.395 (3)	C20—H20	0.9300
C1—C2	1.395 (2)	C21—C21^i	1.529 (4)
C2—C3	1.403 (2)	C21—H21A	1.04 (2)
C2—C7	1.501 (2)	C21—H21B	0.98 (2)
C3—O2	1.367 (2)	C22—N4	1.343 (3)
C3—C4	1.387 (3)	C22—C27	1.417 (3)
C4—C5	1.384 (3)	C22—C23	1.431 (3)
C4—H4	0.9300	C23—C24	1.338 (4)
C5—C6	1.384 (3)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.398 (4)
C6—H6	0.9300	C24—H24	0.9300
C7—H7A	0.9600	C25—C26	1.375 (4)
C7—H7B	0.9600	C25—H25	0.9300
C7—H7C	0.9600	C26—C27	1.433 (3)
C8—N1	1.334 (2)	C26—H26	0.9300
C8—C9	1.401 (3)	C27—C28	1.391 (3)
C8—C12	1.500 (3)	C28—C29	1.388 (3)
C9—N2	1.340 (3)	C28—H28	0.9300
C9—C13	1.499 (3)	C29—C30	1.423 (3)
C10—N2	1.337 (2)	C29—C34	1.430 (3)
C10—C11	1.398 (3)	C30—C31	1.352 (4)
C10—C14	1.501 (3)	C30—H30	0.9300
C11—N1	1.340 (2)	C31—C32	1.408 (4)
C11—C15	1.500 (3)	C31—H31	0.9300
C12—H12A	0.9600	C32—C33	1.357 (4)
C12—H12B	0.9600	C32—H32	0.9300
C12—H12C	0.9600	C33—C34	1.424 (3)
C13—H13A	0.9600	C33—H33	0.9300
C13—H13B	0.9600	C34—N4	1.340 (3)
C13—H13C	0.9600	C35—O3	1.303 (5)
C14—H14A	0.9600	C35—C36	1.385 (4)
C14—H14B	0.9600	C35—C37^ii	1.389 (3)
C14—H14C	0.9600	C36—C39	1.258 (4)
C15—H15A	0.9600	C36—C37	1.386 (4)
C15—H15B	0.9600	C37—C38	1.209 (4)
C15—H15C	0.9600	C37—C35^ii	1.389 (3)
C16—N3	1.337 (2)	C38—H38A	0.9600
C16—C17	1.381 (3)	C38—H38B	0.9600
C16—H16	0.9300	C38—H38C	0.9600
C17—C18	1.386 (2)	C39—H39A	0.9600
C17—H17	0.9300	C39—H39B	0.9600
C18—C19	1.392 (3)	C39—H39C	0.9600
C18—C21	1.512 (2)	O1—H1	0.8200
C19—C20	1.388 (2)	O2—H2	0.8200
C19—H19	0.9300
O1—C1—C6	121.67 (16)	C19—C20—H20	118.3
O1—C1—C2	116.71 (16)	C18—C21—C21^i	112.18 (19)
C6—C1—C2	121.62 (16)	C18—C21—H21A	109.5 (12)
C1—C2—C3	117.62 (16)	C21^i—C21—H21A	105.7 (12)
C1—C2—C7	121.35 (15)	C18—C21—H21B	110.4 (13)
C3—C2—C7	121.03 (15)	C21^i—C21—H21B	108.1 (13)
O2—C3—C4	122.29 (15)	H21A—C21—H21B	110.8 (18)
O2—C3—C2	116.40 (15)	N4—C22—C27	123.12 (19)
C4—C3—C2	121.31 (16)	N4—C22—C23	117.5 (2)
C5—C4—C3	119.48 (16)	C27—C22—C23	119.4 (2)
C5—C4—H4	120.3	C24—C23—C22	121.0 (3)
C3—C4—H4	120.3	C24—C23—H23	119.5
C6—C5—C4	120.94 (17)	C22—C23—H23	119.5
C6—C5—H5	119.5	C23—C24—C25	120.4 (2)
C4—C5—H5	119.5	C23—C24—H24	119.8
C5—C6—C1	119.01 (17)	C25—C24—H24	119.8
C5—C6—H6	120.5	C26—C25—C24	121.3 (2)
C1—C6—H6	120.5	C26—C25—H25	119.3
C2—C7—H7A	109.5	C24—C25—H25	119.3
C2—C7—H7B	109.5	C25—C26—C27	119.9 (3)
H7A—C7—H7B	109.5	C25—C26—H26	120.0
C2—C7—H7C	109.5	C27—C26—H26	120.0
H7A—C7—H7C	109.5	C28—C27—C22	117.99 (19)
H7B—C7—H7C	109.5	C28—C27—C26	124.1 (2)
N1—C8—C9	120.29 (17)	C22—C27—C26	117.9 (2)
N1—C8—C12	117.70 (18)	C29—C28—C27	120.0 (2)
C9—C8—C12	122.01 (18)	C29—C28—H28	120.0
N2—C9—C8	120.02 (17)	C27—C28—H28	120.0
N2—C9—C13	118.20 (18)	C28—C29—C30	123.4 (2)
C8—C9—C13	121.78 (18)	C28—C29—C34	117.79 (19)
N2—C10—C11	120.16 (17)	C30—C29—C34	118.8 (2)
N2—C10—C14	117.93 (17)	C31—C30—C29	120.5 (3)
C11—C10—C14	121.90 (18)	C31—C30—H30	119.8
N1—C11—C10	120.22 (17)	C29—C30—H30	119.8
N1—C11—C15	117.16 (17)	C30—C31—C32	120.9 (2)
C10—C11—C15	122.61 (17)	C30—C31—H31	119.6
C8—C12—H12A	109.5	C32—C31—H31	119.6
C8—C12—H12B	109.5	C33—C32—C31	120.8 (2)
H12A—C12—H12B	109.5	C33—C32—H32	119.6
C8—C12—H12C	109.5	C31—C32—H32	119.6
H12A—C12—H12C	109.5	C32—C33—C34	120.4 (3)
H12B—C12—H12C	109.5	C32—C33—H33	119.8
C9—C13—H13A	109.5	C34—C33—H33	119.8
C9—C13—H13B	109.5	N4—C34—C33	118.6 (2)
H13A—C13—H13B	109.5	N4—C34—C29	122.81 (19)
C9—C13—H13C	109.5	C33—C34—C29	118.6 (2)
H13A—C13—H13C	109.5	O3—C35—C36	118.8 (3)
H13B—C13—H13C	109.5	O3—C35—C37^ii	120.5 (3)
C10—C14—H14A	109.5	C36—C35—C37^ii	120.5 (3)
C10—C14—H14B	109.5	C39—C36—C35	126.6 (3)
H14A—C14—H14B	109.5	C39—C36—C37	113.9 (3)
C10—C14—H14C	109.5	C35—C36—C37	119.4 (2)
H14A—C14—H14C	109.5	C38—C37—C36	115.6 (3)
H14B—C14—H14C	109.5	C38—C37—C35^ii	124.3 (3)
C11—C15—H15A	109.5	C36—C37—C35^ii	120.1 (2)
C11—C15—H15B	109.5	C37—C38—H38A	109.5
H15A—C15—H15B	109.5	C37—C38—H38B	109.5
C11—C15—H15C	109.5	H38A—C38—H38B	109.5
H15A—C15—H15C	109.5	C37—C38—H38C	109.5
H15B—C15—H15C	109.5	H38A—C38—H38C	109.5
N3—C16—C17	123.97 (17)	H38B—C38—H38C	109.5
N3—C16—H16	118.0	C36—C39—H39A	109.5
C17—C16—H16	118.0	C36—C39—H39B	109.5
C16—C17—C18	119.72 (17)	H39A—C39—H39B	109.5
C16—C17—H17	120.1	C36—C39—H39C	109.5
C18—C17—H17	120.1	H39A—C39—H39C	109.5
C17—C18—C19	116.76 (16)	H39B—C39—H39C	109.5
C17—C18—C21	120.55 (16)	C8—N1—C11	119.61 (16)
C19—C18—C21	122.68 (16)	C10—N2—C9	119.69 (16)
C20—C19—C18	119.72 (16)	C16—N3—C20	116.41 (15)
C20—C19—H19	120.1	C34—N4—C22	118.25 (19)
C18—C19—H19	120.1	C1—O1—H1	109.5
N3—C20—C19	123.38 (17)	C3—O2—H2	109.5
N3—C20—H20	118.3
O1—C1—C2—C3	−178.61 (15)	C25—C26—C27—C28	−178.6 (2)
C6—C1—C2—C3	1.8 (3)	C25—C26—C27—C22	1.0 (3)
O1—C1—C2—C7	2.1 (2)	C22—C27—C28—C29	0.7 (3)
C6—C1—C2—C7	−177.52 (16)	C26—C27—C28—C29	−179.7 (2)
C1—C2—C3—O2	179.12 (15)	C27—C28—C29—C30	177.6 (2)
C7—C2—C3—O2	−1.6 (2)	C27—C28—C29—C34	−0.7 (3)
C1—C2—C3—C4	−1.4 (2)	C28—C29—C30—C31	−177.3 (2)
C7—C2—C3—C4	177.88 (16)	C34—C29—C30—C31	0.9 (3)
O2—C3—C4—C5	179.54 (16)	C29—C30—C31—C32	−2.0 (4)
C2—C3—C4—C5	0.1 (3)	C30—C31—C32—C33	1.3 (4)
C3—C4—C5—C6	0.9 (3)	C31—C32—C33—C34	0.5 (4)
C4—C5—C6—C1	−0.5 (3)	C32—C33—C34—N4	177.5 (2)
O1—C1—C6—C5	179.58 (17)	C32—C33—C34—C29	−1.5 (4)
C2—C1—C6—C5	−0.8 (3)	C28—C29—C34—N4	0.2 (3)
N1—C8—C9—N2	0.0 (3)	C30—C29—C34—N4	−178.2 (2)
C12—C8—C9—N2	179.72 (18)	C28—C29—C34—C33	179.1 (2)
N1—C8—C9—C13	−179.25 (18)	C30—C29—C34—C33	0.8 (3)
C12—C8—C9—C13	0.5 (3)	O3—C35—C36—C39	−0.1 (4)
N2—C10—C11—N1	−0.8 (3)	C37^ii—C35—C36—C39	174.9 (3)
C14—C10—C11—N1	177.93 (18)	O3—C35—C36—C37	−175.7 (3)
N2—C10—C11—C15	179.91 (19)	C37^ii—C35—C36—C37	−0.7 (4)
C14—C10—C11—C15	−1.4 (3)	C39—C36—C37—C38	6.9 (4)
N3—C16—C17—C18	0.4 (3)	C35—C36—C37—C38	−177.0 (3)
C16—C17—C18—C19	1.3 (3)	C39—C36—C37—C35^ii	−175.5 (2)
C16—C17—C18—C21	−178.51 (17)	C35—C36—C37—C35^ii	0.7 (4)
C17—C18—C19—C20	−1.6 (3)	C9—C8—N1—C11	−1.2 (3)
C21—C18—C19—C20	178.20 (16)	C12—C8—N1—C11	179.02 (18)
C18—C19—C20—N3	0.3 (3)	C10—C11—N1—C8	1.6 (3)
C17—C18—C21—C21^i	−67.4 (3)	C15—C11—N1—C8	−179.03 (18)
C19—C18—C21—C21^i	112.8 (2)	C11—C10—N2—C9	−0.5 (3)
N4—C22—C23—C24	178.9 (2)	C14—C10—N2—C9	−179.24 (18)
C27—C22—C23—C24	−1.5 (3)	C8—C9—N2—C10	0.9 (3)
C22—C23—C24—C25	0.8 (4)	C13—C9—N2—C10	−179.88 (18)
C23—C24—C25—C26	0.8 (4)	C17—C16—N3—C20	−1.7 (3)
C24—C25—C26—C27	−1.7 (4)	C19—C20—N3—C16	1.3 (3)
N4—C22—C27—C28	−0.2 (3)	C33—C34—N4—C22	−178.7 (2)
C23—C22—C27—C28	−179.8 (2)	C29—C34—N4—C22	0.3 (3)
N4—C22—C27—C26	−179.9 (2)	C27—C22—N4—C34	−0.2 (3)
C23—C22—C27—C26	0.6 (3)	C23—C22—N4—C34	179.4 (2)

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

(MRE_TMP_DPE-II_ANT)

Crystal data

C77H77N6O6	V = 1554.77 (11) Å^3
Mr = 1182.44	Z = 1
Triclinic, P1	F(000) = 629
a = 7.4914 (3) Å	Dx = 1.263 Mg m^−3
b = 8.8265 (4) Å	Mo Kα radiation, λ = 0.71073 Å
c = 23.583 (1) Å	µ = 0.08 mm^−1
α = 92.722 (1)°	T = 150 K
β = 92.976 (1)°	Block, colorless
γ = 91.626 (1)°	0.88 × 0.39 × 0.22 mm

Data collection

CCD area detector diffractometer	4165 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.080
phi and ω scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: analytical Bruker, AXS, 2008	h = −9→9
Tmin = 0.963, Tmax = 0.983	k = −10→10
36300 measured reflections	l = −29→29
6096 independent reflections

Refinement

Refinement on F^2	10 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.164	w = 1/[σ^2(Fo^2) + (0.0955P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.021
6096 reflections	Δρmax = 0.31 e Å^−3
433 parameters	Δρmin = −0.30 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
H22A	−0.564 (3)	1.396 (2)	0.0411 (8)	0.025 (5)*
H22B	−0.486 (2)	1.567 (2)	0.0570 (8)	0.025 (5)*
O1	0.57452 (17)	0.71363 (15)	0.17027 (6)	0.0290 (4)
H1	0.5497	0.6604	0.1976	0.044*
O2	0.34266 (17)	1.10855 (14)	0.06395 (5)	0.0255 (3)
H2	0.2525	1.1626	0.0609	0.038*
N1	0.4901 (2)	0.53664 (17)	0.26129 (6)	0.0239 (4)
N2	0.4740 (2)	0.34175 (17)	0.34810 (6)	0.0237 (4)
N3	0.0529 (2)	1.29792 (17)	0.04831 (6)	0.0240 (4)
C2	0.4319 (2)	0.8003 (2)	0.15619 (7)	0.0189 (4)
C7	0.3143 (2)	1.00096 (19)	0.10256 (7)	0.0185 (4)
C1	0.4583 (2)	0.90938 (19)	0.11590 (7)	0.0160 (4)
C12	0.5400 (2)	0.5846 (2)	0.31464 (8)	0.0217 (4)
C9	0.4274 (2)	0.3943 (2)	0.25096 (8)	0.0235 (4)
C6	0.1508 (3)	0.9826 (2)	0.12688 (8)	0.0243 (4)
H6	0.0548	1.0461	0.1171	0.029*
C18	−0.1501 (2)	1.4964 (2)	0.06684 (8)	0.0224 (4)
H18	−0.1685	1.5936	0.0842	0.027*
C10	0.4188 (2)	0.2952 (2)	0.29508 (8)	0.0223 (4)
C19	−0.2910 (2)	1.4172 (2)	0.03664 (7)	0.0186 (4)
C11	0.5340 (2)	0.4849 (2)	0.35877 (8)	0.0215 (4)
C8	0.6316 (2)	0.9240 (2)	0.08756 (8)	0.0219 (4)
H8A	0.7292	0.8922	0.1132	0.033*
H8B	0.6530	1.0299	0.0784	0.033*
H8C	0.6262	0.8595	0.0525	0.033*
C17	0.0161 (3)	1.4335 (2)	0.07147 (8)	0.0240 (4)
H17	0.1097	1.4899	0.0923	0.029*
C22	−0.4756 (3)	1.4779 (2)	0.03042 (8)	0.0224 (4)
C3	0.2686 (3)	0.7808 (2)	0.18042 (8)	0.0260 (5)
H3	0.2530	0.7053	0.2073	0.031*
C20	−0.2515 (3)	1.2775 (2)	0.01213 (8)	0.0271 (5)
H20	−0.3422	1.2186	−0.0091	0.033*
C5	0.1288 (3)	0.8717 (2)	0.16534 (8)	0.0285 (5)
H5	0.0164	0.8577	0.1816	0.034*
C21	−0.0820 (3)	1.2235 (2)	0.01837 (8)	0.0286 (5)
H21	−0.0590	1.1279	0.0004	0.034*
C14	0.3501 (3)	0.1344 (2)	0.28500 (10)	0.0353 (5)
H14A	0.3545	0.0834	0.3210	0.053*
H14B	0.4246	0.0810	0.2581	0.053*
H14C	0.2263	0.1337	0.2693	0.053*
C13	0.3669 (3)	0.3468 (2)	0.19099 (9)	0.0374 (5)
H13A	0.2364	0.3330	0.1882	0.056*
H13B	0.4217	0.2510	0.1800	0.056*
H13C	0.4029	0.4252	0.1655	0.056*
C16	0.6017 (3)	0.7471 (2)	0.32434 (9)	0.0360 (5)
H16A	0.5825	0.8003	0.2891	0.054*
H16B	0.7293	0.7519	0.3360	0.054*
H16C	0.5337	0.7955	0.3543	0.054*
C15	0.5958 (3)	0.5323 (3)	0.41833 (8)	0.0353 (5)
H15A	0.5655	0.4518	0.4437	0.053*
H15B	0.5369	0.6256	0.4300	0.053*
H15C	0.7257	0.5508	0.4203	0.053*
C36	−0.0173 (3)	0.5367 (2)	0.27882 (9)	0.0338 (5)
H36	−0.0199	0.6069	0.2495	0.041*
C28	−0.0771 (3)	0.2835 (2)	0.30995 (9)	0.0324 (5)
C30	0.0501 (3)	0.4796 (3)	0.37707 (9)	0.0333 (5)
C29	−0.0122 (3)	0.3309 (2)	0.36401 (10)	0.0362 (5)
H29	−0.0100	0.2602	0.3932	0.043*
C35	0.0481 (3)	0.5857 (2)	0.33284 (9)	0.0319 (5)
C23	−0.0791 (3)	0.3889 (2)	0.26610 (9)	0.0322 (5)
C27	−0.1424 (3)	0.1313 (3)	0.29517 (12)	0.0517 (7)
H27	−0.1434	0.0581	0.3234	0.062*
C34	0.1089 (3)	0.7379 (3)	0.34688 (12)	0.0523 (7)
H34	0.1098	0.8096	0.3181	0.063*
C24	−0.1466 (3)	0.3390 (3)	0.21061 (10)	0.0533 (7)
H24	−0.1498	0.4092	0.1813	0.064*
C26	−0.2029 (3)	0.0915 (3)	0.24087 (16)	0.0681 (10)
H26	−0.2441	−0.0099	0.2317	0.082*
C32	0.1665 (4)	0.6756 (4)	0.44393 (14)	0.0722 (9)
H32	0.2061	0.7078	0.4816	0.087*
C31	0.1129 (3)	0.5315 (3)	0.43268 (11)	0.0547 (7)
H31	0.1167	0.4624	0.4624	0.066*
C25	−0.2055 (4)	0.1960 (4)	0.19865 (14)	0.0715 (10)
H25	−0.2492	0.1658	0.1612	0.086*
C33	0.1655 (4)	0.7813 (4)	0.40076 (16)	0.0738 (10)
H33	0.2047	0.8834	0.4096	0.089*
C38	0.6661 (4)	0.9517 (3)	0.48276 (10)	0.0467 (7)
C39	0.5909 (4)	0.8911 (3)	0.53001 (10)	0.0520 (8)
C37	0.5740 (4)	1.0610 (3)	0.45310 (11)	0.0533 (8)
O3	0.6308 (4)	1.1261 (3)	0.41344 (11)	0.0312 (7)	0.5
H3A	0.5481	1.1737	0.3976	0.047*	0.5
O4	0.6636 (4)	0.8006 (3)	0.56187 (12)	0.0341 (7)	0.5
H4	0.5919	0.7745	0.5861	0.051*	0.5
C40	0.8215 (5)	0.9156 (4)	0.47039 (16)	0.0224 (8)	0.5
H40A	0.9088	0.9616	0.4990	0.034*	0.5
H40B	0.8466	0.9522	0.4329	0.034*	0.5
H40C	0.8300	0.8049	0.4696	0.034*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0271 (8)	0.0322 (8)	0.0304 (8)	0.0128 (6)	0.0052 (6)	0.0176 (6)
O2	0.0255 (8)	0.0255 (8)	0.0278 (8)	0.0104 (6)	0.0063 (6)	0.0138 (6)
N1	0.0294 (9)	0.0199 (9)	0.0225 (9)	0.0030 (7)	−0.0016 (7)	0.0059 (7)
N2	0.0250 (9)	0.0217 (9)	0.0253 (9)	0.0034 (7)	0.0043 (7)	0.0076 (7)
N3	0.0237 (9)	0.0231 (9)	0.0261 (9)	0.0061 (7)	−0.0007 (7)	0.0089 (7)
C2	0.0224 (10)	0.0175 (9)	0.0171 (9)	0.0066 (8)	0.0003 (8)	0.0016 (7)
C7	0.0255 (10)	0.0161 (9)	0.0140 (9)	0.0037 (8)	0.0002 (8)	0.0016 (7)
C1	0.0177 (10)	0.0159 (9)	0.0138 (9)	0.0009 (7)	−0.0003 (7)	−0.0034 (7)
C12	0.0223 (10)	0.0191 (10)	0.0237 (11)	0.0030 (8)	0.0001 (8)	0.0012 (8)
C9	0.0238 (11)	0.0219 (10)	0.0245 (11)	0.0043 (8)	−0.0039 (8)	0.0010 (8)
C6	0.0216 (10)	0.0253 (11)	0.0275 (11)	0.0090 (8)	0.0051 (8)	0.0056 (8)
C18	0.0273 (11)	0.0194 (10)	0.0205 (10)	0.0056 (8)	−0.0011 (8)	−0.0003 (8)
C10	0.0192 (10)	0.0207 (10)	0.0274 (11)	0.0026 (8)	0.0019 (8)	0.0011 (8)
C19	0.0207 (10)	0.0179 (9)	0.0177 (9)	0.0035 (8)	0.0006 (8)	0.0073 (7)
C11	0.0202 (10)	0.0223 (10)	0.0223 (10)	0.0042 (8)	0.0018 (8)	0.0017 (8)
C8	0.0207 (10)	0.0249 (10)	0.0200 (10)	0.0019 (8)	0.0000 (8)	0.0010 (8)
C17	0.0228 (11)	0.0258 (11)	0.0232 (10)	0.0023 (8)	−0.0047 (8)	0.0041 (8)
C22	0.0207 (11)	0.0230 (10)	0.0237 (10)	0.0048 (8)	−0.0012 (8)	0.0043 (9)
C3	0.0288 (11)	0.0247 (11)	0.0266 (11)	0.0055 (8)	0.0091 (9)	0.0123 (8)
C20	0.0271 (11)	0.0186 (10)	0.0347 (12)	0.0032 (8)	−0.0077 (9)	0.0000 (8)
C5	0.0233 (11)	0.0315 (11)	0.0328 (12)	0.0063 (9)	0.0106 (9)	0.0096 (9)
C21	0.0340 (12)	0.0176 (10)	0.0339 (12)	0.0084 (9)	−0.0045 (9)	−0.0008 (9)
C14	0.0358 (13)	0.0202 (11)	0.0498 (14)	−0.0015 (9)	0.0038 (11)	0.0020 (10)
C13	0.0451 (14)	0.0365 (13)	0.0290 (12)	−0.0003 (10)	−0.0102 (10)	0.0002 (10)
C16	0.0460 (14)	0.0202 (11)	0.0412 (13)	−0.0012 (10)	0.0011 (11)	−0.0022 (9)
C15	0.0406 (13)	0.0427 (13)	0.0223 (11)	0.0069 (10)	−0.0004 (9)	−0.0016 (9)
C36	0.0341 (12)	0.0356 (13)	0.0330 (12)	−0.0029 (10)	0.0144 (10)	0.0038 (10)
C28	0.0230 (11)	0.0286 (11)	0.0462 (14)	−0.0014 (9)	0.0180 (10)	−0.0084 (10)
C30	0.0233 (11)	0.0448 (14)	0.0316 (12)	0.0048 (10)	0.0051 (9)	−0.0085 (10)
C29	0.0318 (12)	0.0374 (13)	0.0414 (13)	0.0088 (10)	0.0129 (10)	0.0077 (10)
C35	0.0246 (11)	0.0304 (12)	0.0406 (13)	−0.0033 (9)	0.0120 (10)	−0.0081 (10)
C23	0.0248 (11)	0.0403 (13)	0.0313 (12)	−0.0034 (9)	0.0138 (9)	−0.0094 (10)
C27	0.0382 (14)	0.0312 (13)	0.087 (2)	−0.0039 (11)	0.0354 (14)	−0.0119 (13)
C34	0.0435 (15)	0.0355 (14)	0.0771 (19)	−0.0140 (11)	0.0221 (13)	−0.0170 (13)
C24	0.0406 (15)	0.0821 (19)	0.0357 (14)	−0.0081 (14)	0.0156 (11)	−0.0225 (13)
C26	0.0373 (15)	0.0555 (18)	0.108 (3)	−0.0155 (14)	0.0353 (16)	−0.0580 (18)
C32	0.0426 (17)	0.105 (3)	0.063 (2)	−0.0048 (17)	−0.0057 (15)	−0.0479 (19)
C31	0.0370 (15)	0.085 (2)	0.0403 (15)	0.0096 (14)	−0.0037 (11)	−0.0157 (14)
C25	0.0432 (16)	0.095 (2)	0.071 (2)	−0.0203 (17)	0.0228 (15)	−0.0583 (19)
C33	0.0505 (18)	0.064 (2)	0.102 (3)	−0.0259 (15)	0.0206 (17)	−0.0536 (19)
C38	0.0638 (18)	0.0319 (13)	0.0408 (14)	−0.0241 (12)	−0.0258 (13)	0.0118 (10)
C39	0.076 (2)	0.0352 (14)	0.0416 (15)	−0.0281 (14)	−0.0326 (14)	0.0206 (11)
C37	0.077 (2)	0.0352 (14)	0.0436 (15)	−0.0313 (14)	−0.0364 (14)	0.0208 (11)
O3	0.0363 (17)	0.0365 (17)	0.0238 (15)	0.0101 (13)	0.0096 (13)	0.0182 (13)
O4	0.0347 (17)	0.0372 (17)	0.0335 (17)	0.0124 (14)	0.0072 (13)	0.0223 (13)
C40	0.022 (2)	0.024 (2)	0.022 (2)	0.0024 (16)	0.0024 (16)	0.0031 (16)

Geometric parameters (Å, º)

O1—C2	1.368 (2)	C13—H13C	0.9800
O1—H1	0.8400	C16—H16A	0.9800
O2—C7	1.366 (2)	C16—H16B	0.9800
O2—H2	0.8400	C16—H16C	0.9800
N1—C9	1.336 (2)	C15—H15A	0.9800
N1—C12	1.339 (2)	C15—H15B	0.9800
N2—C11	1.337 (2)	C15—H15C	0.9800
N2—C10	1.338 (2)	C36—C35	1.386 (3)
N3—C17	1.333 (2)	C36—C23	1.386 (3)
N3—C21	1.340 (2)	C36—H36	0.9500
C2—C3	1.387 (3)	C28—C29	1.382 (3)
C2—C1	1.401 (2)	C28—C23	1.423 (3)
C7—C6	1.387 (3)	C28—C27	1.437 (3)
C7—C1	1.398 (2)	C30—C29	1.395 (3)
C1—C8	1.496 (2)	C30—C31	1.421 (3)
C12—C11	1.396 (2)	C30—C35	1.435 (3)
C12—C16	1.498 (3)	C29—H29	0.9500
C9—C10	1.394 (3)	C35—C34	1.424 (3)
C9—C13	1.499 (3)	C23—C24	1.423 (3)
C6—C5	1.378 (3)	C27—C26	1.362 (4)
C6—H6	0.9500	C27—H27	0.9500
C18—C17	1.379 (3)	C34—C33	1.353 (4)
C18—C19	1.394 (3)	C34—H34	0.9500
C18—H18	0.9500	C24—C25	1.338 (4)
C10—C14	1.500 (3)	C24—H24	0.9500
C19—C20	1.383 (3)	C26—C25	1.389 (4)
C19—C22	1.500 (3)	C26—H26	0.9500
C11—C15	1.493 (3)	C32—C31	1.333 (4)
C8—H8A	0.9800	C32—C33	1.413 (5)
C8—H8B	0.9800	C32—H32	0.9500
C8—H8C	0.9800	C31—H31	0.9500
C17—H17	0.9500	C25—H25	0.9500
C22—C22^i	1.533 (4)	C33—H33	0.9500
C22—H22A	1.02 (2)	C38—C40	1.261 (4)
C22—H22B	0.99 (2)	C38—C37	1.396 (3)
C3—C5	1.379 (3)	C38—C39	1.396 (3)
C3—H3	0.9500	C39—O4	1.240 (3)
C20—C21	1.372 (3)	C39—C37^ii	1.389 (4)
C20—H20	0.9500	C37—O3	1.211 (3)
C5—H5	0.9500	C37—C39^ii	1.388 (4)
C21—H21	0.9500	O3—H3A	0.8400
C14—H14A	0.9800	O4—H4	0.8400
C14—H14B	0.9800	C40—H40A	0.9800
C14—H14C	0.9800	C40—H40B	0.9800
C13—H13A	0.9800	C40—H40C	0.9800
C13—H13B	0.9800
C2—O1—H1	109.5	H13B—C13—H13C	109.5
C7—O2—H2	109.5	C12—C16—H16A	109.5
C9—N1—C12	119.47 (16)	C12—C16—H16B	109.5
C11—N2—C10	119.66 (16)	H16A—C16—H16B	109.5
C17—N3—C21	116.19 (16)	C12—C16—H16C	109.5
O1—C2—C3	121.62 (16)	H16A—C16—H16C	109.5
O1—C2—C1	116.86 (16)	H16B—C16—H16C	109.5
C3—C2—C1	121.52 (16)	C11—C15—H15A	109.5
O2—C7—C6	121.81 (16)	C11—C15—H15B	109.5
O2—C7—C1	116.43 (15)	H15A—C15—H15B	109.5
C6—C7—C1	121.75 (16)	C11—C15—H15C	109.5
C7—C1—C2	116.99 (16)	H15A—C15—H15C	109.5
C7—C1—C8	121.76 (16)	H15B—C15—H15C	109.5
C2—C1—C8	121.23 (16)	C35—C36—C23	122.3 (2)
N1—C12—C11	120.32 (16)	C35—C36—H36	118.9
N1—C12—C16	117.37 (16)	C23—C36—H36	118.9
C11—C12—C16	122.30 (17)	C29—C28—C23	119.10 (19)
N1—C9—C10	120.27 (17)	C29—C28—C27	123.3 (2)
N1—C9—C13	117.79 (17)	C23—C28—C27	117.6 (2)
C10—C9—C13	121.94 (17)	C29—C30—C31	122.8 (2)
C5—C6—C7	119.53 (17)	C29—C30—C35	118.86 (19)
C5—C6—H6	120.2	C31—C30—C35	118.3 (2)
C7—C6—H6	120.2	C28—C29—C30	122.0 (2)
C17—C18—C19	119.92 (17)	C28—C29—H29	119.0
C17—C18—H18	120.0	C30—C29—H29	119.0
C19—C18—H18	120.0	C36—C35—C34	123.0 (2)
N2—C10—C9	120.22 (17)	C36—C35—C30	118.58 (19)
N2—C10—C14	118.03 (17)	C34—C35—C30	118.4 (2)
C9—C10—C14	121.74 (17)	C36—C23—C28	119.17 (19)
C20—C19—C18	116.12 (17)	C36—C23—C24	122.1 (2)
C20—C19—C22	121.09 (17)	C28—C23—C24	118.7 (2)
C18—C19—C22	122.79 (16)	C26—C27—C28	120.4 (3)
N2—C11—C12	119.99 (16)	C26—C27—H27	119.8
N2—C11—C15	118.11 (17)	C28—C27—H27	119.8
C12—C11—C15	121.89 (17)	C33—C34—C35	120.7 (3)
C1—C8—H8A	109.5	C33—C34—H34	119.7
C1—C8—H8B	109.5	C35—C34—H34	119.7
H8A—C8—H8B	109.5	C25—C24—C23	121.8 (3)
C1—C8—H8C	109.5	C25—C24—H24	119.1
H8A—C8—H8C	109.5	C23—C24—H24	119.1
H8B—C8—H8C	109.5	C27—C26—C25	121.4 (2)
N3—C17—C18	123.70 (18)	C27—C26—H26	119.3
N3—C17—H17	118.1	C25—C26—H26	119.3
C18—C17—H17	118.1	C31—C32—C33	121.2 (3)
C19—C22—C22^i	112.5 (2)	C31—C32—H32	119.4
C19—C22—H22A	108.0 (11)	C33—C32—H32	119.4
C22^i—C22—H22A	108.8 (10)	C32—C31—C30	121.1 (3)
C19—C22—H22B	110.0 (11)	C32—C31—H31	119.4
C22^i—C22—H22B	109.4 (11)	C30—C31—H31	119.4
H22A—C22—H22B	108.1 (15)	C24—C25—C26	120.2 (3)
C5—C3—C2	119.67 (17)	C24—C25—H25	119.9
C5—C3—H3	120.2	C26—C25—H25	119.9
C2—C3—H3	120.2	C34—C33—C32	120.3 (3)
C21—C20—C19	120.31 (18)	C34—C33—H33	119.8
C21—C20—H20	119.8	C32—C33—H33	119.8
C19—C20—H20	119.8	C40—C38—C37	121.1 (3)
C6—C5—C3	120.50 (18)	C40—C38—C39	119.4 (3)
C6—C5—H5	119.7	C37—C38—C39	119.2 (3)
C3—C5—H5	119.7	O4—C39—C37^ii	114.3 (3)
N3—C21—C20	123.73 (18)	O4—C39—C38	125.5 (3)
N3—C21—H21	118.1	C37^ii—C39—C38	120.1 (2)
C20—C21—H21	118.1	O3—C37—C39^ii	114.6 (3)
C10—C14—H14A	109.5	O3—C37—C38	124.6 (3)
C10—C14—H14B	109.5	C39^ii—C37—C38	120.7 (2)
H14A—C14—H14B	109.5	C37—O3—H3A	109.5
C10—C14—H14C	109.5	C39—O4—H4	109.5
H14A—C14—H14C	109.5	C38—C40—H40A	109.5
H14B—C14—H14C	109.5	C38—C40—H40B	109.5
C9—C13—H13A	109.5	H40A—C40—H40B	109.5
C9—C13—H13B	109.5	C38—C40—H40C	109.5
H13A—C13—H13B	109.5	H40A—C40—H40C	109.5
C9—C13—H13C	109.5	H40B—C40—H40C	109.5
H13A—C13—H13C	109.5

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

(MRE_TMP_DPE-II_DP)

Crystal data

C46H50N4O4	V = 948.9 (3) Å^3
Mr = 722.90	Z = 1
Triclinic, P1	F(000) = 386
a = 7.5407 (12) Å	Dx = 1.265 Mg m^−3
b = 8.9198 (13) Å	Mo Kα radiation, λ = 0.71073 Å
c = 14.284 (3) Å	µ = 0.08 mm^−1
α = 96.506 (7)°	T = 150 K
β = 96.093 (10)°	Block, colorless
γ = 90.634 (10)°	0.48 × 0.38 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3687 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.093
profile data from ω–scans	θmax = 27.6°, θmin = 1.4°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.699, Tmax = 1.000	k = −11→11
10144 measured reflections	l = −18→18
4338 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.169	w = 1/[σ^2(Fo^2) + (0.0815P)^2 + 0.1168P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
4338 reflections	Δρmax = 0.35 e Å^−3
257 parameters	Δρmin = −0.25 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
H17A	−0.974 (3)	1.577 (2)	0.5922 (16)	0.042 (5)*
H17B	−1.060 (3)	1.410 (2)	0.5722 (16)	0.044 (5)*
O1	0.11600 (14)	0.74909 (12)	0.77875 (8)	0.0302 (3)
H1	0.0920	0.6941	0.8200	0.045*
O2	−0.13940 (14)	1.12835 (12)	0.60492 (8)	0.0290 (3)
H2	−0.2308	1.1812	0.6003	0.044*
N1	0.03319 (16)	0.58255 (13)	0.92772 (9)	0.0237 (3)
N2	−0.43670 (18)	1.31028 (15)	0.58177 (10)	0.0306 (3)
C1	−0.01229 (18)	0.93674 (15)	0.68965 (9)	0.0214 (3)
C5	−0.3232 (2)	1.00202 (17)	0.70110 (11)	0.0283 (3)
H5	−0.4226	1.0616	0.6841	0.034*
C2	−0.03121 (19)	0.83044 (15)	0.75275 (10)	0.0229 (3)
C10	0.06533 (18)	0.64368 (15)	1.01830 (10)	0.0229 (3)
C6	−0.16135 (19)	1.02357 (15)	0.66531 (10)	0.0223 (3)
C14	−0.7835 (2)	1.42582 (16)	0.56229 (11)	0.0264 (3)
C4	−0.3379 (2)	0.89313 (18)	0.76166 (12)	0.0320 (4)
H4	−0.4488	0.8772	0.7854	0.038*
C9	−0.03257 (19)	0.44054 (16)	0.90808 (10)	0.0239 (3)
C11	0.1345 (2)	0.80387 (16)	1.03731 (13)	0.0324 (4)
H11A	0.1421	0.8449	0.9770	0.049*
H11B	0.2533	0.8067	1.0728	0.049*
H11C	0.0534	0.8645	1.0745	0.049*
C7	0.1584 (2)	0.95655 (18)	0.64636 (11)	0.0289 (3)
H7A	0.2544	0.9047	0.6806	0.043*
H7B	0.1892	1.0643	0.6505	0.043*
H7C	0.1429	0.9135	0.5797	0.043*
C12	−0.4741 (2)	1.44699 (18)	0.62312 (12)	0.0315 (3)
H12	−0.3797	1.5055	0.6596	0.038*
C3	−0.1933 (2)	0.80679 (17)	0.78824 (12)	0.0295 (3)
H3	−0.2045	0.7325	0.8301	0.035*
C13	−0.6426 (2)	1.50789 (17)	0.61567 (11)	0.0297 (3)
H13	−0.6616	1.6053	0.6469	0.036*
C17	−0.9706 (2)	1.48507 (19)	0.55112 (11)	0.0301 (3)
C8	−0.0724 (2)	0.37784 (19)	0.80619 (11)	0.0352 (4)
H8A	−0.0339	0.4511	0.7658	0.053*
H8B	−0.2010	0.3577	0.7916	0.053*
H8C	−0.0084	0.2837	0.7945	0.053*
C15	−0.7448 (2)	1.28487 (17)	0.51778 (12)	0.0332 (4)
H15	−0.8361	1.2247	0.4799	0.040*
C16	−0.5724 (2)	1.23294 (18)	0.52912 (13)	0.0345 (4)
H16	−0.5490	1.1367	0.4977	0.041*
C18	0.46552 (19)	0.42534 (17)	0.97548 (11)	0.0273 (3)
C23	0.4335 (3)	0.3058 (2)	1.02619 (13)	0.0405 (4)
H23	0.4576	0.3189	1.0933	0.049*
C20	0.3674 (3)	0.2601 (2)	0.83188 (14)	0.0448 (4)
H20	0.3468	0.2451	0.7647	0.054*
C21	0.3333 (2)	0.1435 (2)	0.88354 (14)	0.0391 (4)
H21	0.2877	0.0488	0.8527	0.047*
C19	0.4314 (3)	0.39929 (19)	0.87692 (13)	0.0402 (4)
H19	0.4525	0.4784	0.8399	0.048*
C22	0.3669 (3)	0.1670 (2)	0.98082 (14)	0.0442 (5)
H22	0.3443	0.0876	1.0174	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0268 (6)	0.0376 (6)	0.0297 (6)	0.0097 (4)	0.0060 (4)	0.0151 (5)
O2	0.0299 (6)	0.0335 (6)	0.0265 (6)	0.0087 (4)	0.0059 (4)	0.0122 (4)
N1	0.0228 (6)	0.0255 (6)	0.0233 (6)	0.0023 (4)	0.0009 (5)	0.0063 (5)
N2	0.0284 (7)	0.0343 (7)	0.0305 (7)	0.0077 (5)	0.0013 (5)	0.0107 (5)
C1	0.0222 (7)	0.0245 (6)	0.0170 (6)	0.0006 (5)	0.0014 (5)	0.0008 (5)
C5	0.0241 (7)	0.0339 (7)	0.0284 (8)	0.0087 (6)	0.0037 (6)	0.0085 (6)
C2	0.0236 (7)	0.0263 (6)	0.0190 (7)	0.0036 (5)	0.0021 (5)	0.0028 (5)
C10	0.0194 (7)	0.0243 (6)	0.0247 (7)	0.0029 (5)	0.0003 (5)	0.0038 (5)
C6	0.0256 (7)	0.0244 (6)	0.0164 (6)	0.0019 (5)	0.0014 (5)	0.0015 (5)
C14	0.0271 (7)	0.0311 (7)	0.0216 (7)	0.0041 (6)	0.0005 (5)	0.0078 (6)
C4	0.0228 (7)	0.0422 (8)	0.0341 (9)	0.0048 (6)	0.0086 (6)	0.0116 (7)
C9	0.0215 (7)	0.0268 (7)	0.0230 (7)	0.0024 (5)	0.0000 (5)	0.0028 (5)
C11	0.0328 (8)	0.0256 (7)	0.0382 (9)	−0.0037 (6)	0.0020 (7)	0.0027 (6)
C7	0.0247 (8)	0.0376 (8)	0.0258 (8)	0.0019 (6)	0.0057 (6)	0.0074 (6)
C12	0.0294 (8)	0.0349 (8)	0.0293 (8)	0.0005 (6)	−0.0042 (6)	0.0065 (6)
C3	0.0292 (8)	0.0331 (7)	0.0294 (8)	0.0043 (6)	0.0086 (6)	0.0123 (6)
C13	0.0328 (8)	0.0295 (7)	0.0251 (8)	0.0055 (6)	−0.0024 (6)	0.0004 (6)
C17	0.0257 (8)	0.0400 (8)	0.0251 (8)	0.0080 (6)	0.0016 (6)	0.0067 (6)
C8	0.0426 (10)	0.0390 (8)	0.0220 (8)	−0.0021 (7)	−0.0017 (6)	0.0007 (6)
C15	0.0328 (9)	0.0296 (7)	0.0342 (9)	0.0027 (6)	−0.0074 (6)	0.0014 (6)
C16	0.0376 (9)	0.0289 (7)	0.0356 (9)	0.0087 (6)	−0.0020 (7)	0.0016 (6)
C18	0.0199 (7)	0.0354 (8)	0.0265 (8)	0.0046 (6)	0.0062 (5)	−0.0003 (6)
C23	0.0434 (10)	0.0490 (10)	0.0292 (9)	−0.0166 (8)	0.0102 (7)	0.0004 (7)
C20	0.0566 (12)	0.0441 (9)	0.0304 (9)	0.0055 (8)	0.0015 (8)	−0.0073 (7)
C21	0.0310 (9)	0.0396 (9)	0.0440 (10)	−0.0018 (7)	0.0082 (7)	−0.0105 (7)
C19	0.0539 (11)	0.0361 (8)	0.0297 (9)	0.0057 (7)	0.0028 (8)	0.0009 (7)
C22	0.0458 (11)	0.0457 (9)	0.0419 (10)	−0.0160 (8)	0.0133 (8)	0.0020 (8)

Geometric parameters (Å, º)

O1—C2	1.3740 (17)	C7—H7B	0.9800
O1—H1	0.8400	C7—H7C	0.9800
O2—C6	1.3618 (17)	C12—C13	1.386 (2)
O2—H2	0.8400	C12—H12	0.9500
N1—C10	1.3419 (19)	C3—H3	0.9500
N1—C9	1.3436 (19)	C13—H13	0.9500
N2—C12	1.340 (2)	C17—C17^ii	1.534 (3)
N2—C16	1.339 (2)	C17—H17A	0.96 (2)
C1—C2	1.3964 (19)	C17—H17B	1.04 (2)
C1—C6	1.4077 (19)	C8—H8A	0.9800
C1—C7	1.5028 (19)	C8—H8B	0.9800
C5—C4	1.383 (2)	C8—H8C	0.9800
C5—C6	1.392 (2)	C15—C16	1.384 (2)
C5—H5	0.9500	C15—H15	0.9500
C2—C3	1.395 (2)	C16—H16	0.9500
C10—C9^i	1.400 (2)	C18—C23	1.388 (2)
C10—C11	1.5011 (19)	C18—C19	1.396 (2)
C14—C13	1.390 (2)	C18—C18^iii	1.494 (3)
C14—C15	1.391 (2)	C23—C22	1.393 (2)
C14—C17	1.511 (2)	C23—H23	0.9500
C4—C3	1.387 (2)	C20—C21	1.379 (3)
C4—H4	0.9500	C20—C19	1.388 (3)
C9—C10^i	1.400 (2)	C20—H20	0.9500
C9—C8	1.497 (2)	C21—C22	1.377 (3)
C11—H11A	0.9800	C21—H21	0.9500
C11—H11B	0.9800	C19—H19	0.9500
C11—H11C	0.9800	C22—H22	0.9500
C7—H7A	0.9800
C2—O1—H1	109.5	C4—C3—C2	119.15 (13)
C6—O2—H2	109.5	C4—C3—H3	120.4
C10—N1—C9	119.54 (12)	C2—C3—H3	120.4
C12—N2—C16	116.26 (13)	C12—C13—C14	119.66 (14)
C2—C1—C6	117.65 (12)	C12—C13—H13	120.2
C2—C1—C7	121.99 (12)	C14—C13—H13	120.2
C6—C1—C7	120.34 (12)	C14—C17—C17^ii	112.12 (16)
C4—C5—C6	119.39 (13)	C14—C17—H17A	108.2 (13)
C4—C5—H5	120.3	C17^ii—C17—H17A	109.2 (13)
C6—C5—H5	120.3	C14—C17—H17B	110.3 (12)
O1—C2—C3	120.89 (12)	C17^ii—C17—H17B	109.5 (13)
O1—C2—C1	117.58 (12)	H17A—C17—H17B	107.3 (18)
C3—C2—C1	121.53 (13)	C9—C8—H8A	109.5
N1—C10—C9^i	120.25 (13)	C9—C8—H8B	109.5
N1—C10—C11	117.98 (13)	H8A—C8—H8B	109.5
C9^i—C10—C11	121.76 (14)	C9—C8—H8C	109.5
O2—C6—C5	121.96 (12)	H8A—C8—H8C	109.5
O2—C6—C1	116.78 (12)	H8B—C8—H8C	109.5
C5—C6—C1	121.26 (13)	C16—C15—C14	119.57 (15)
C13—C14—C15	116.85 (14)	C16—C15—H15	120.2
C13—C14—C17	122.53 (14)	C14—C15—H15	120.2
C15—C14—C17	120.62 (14)	N2—C16—C15	123.89 (14)
C5—C4—C3	120.99 (14)	N2—C16—H16	118.1
C5—C4—H4	119.5	C15—C16—H16	118.1
C3—C4—H4	119.5	C23—C18—C19	117.03 (15)
N1—C9—C10^i	120.20 (13)	C23—C18—C18^iii	121.25 (18)
N1—C9—C8	118.06 (13)	C19—C18—C18^iii	121.72 (18)
C10^i—C9—C8	121.72 (13)	C18—C23—C22	121.44 (16)
C10—C11—H11A	109.5	C18—C23—H23	119.3
C10—C11—H11B	109.5	C22—C23—H23	119.3
H11A—C11—H11B	109.5	C21—C20—C19	120.79 (17)
C10—C11—H11C	109.5	C21—C20—H20	119.6
H11A—C11—H11C	109.5	C19—C20—H20	119.6
H11B—C11—H11C	109.5	C22—C21—C20	118.63 (16)
C1—C7—H7A	109.5	C22—C21—H21	120.7
C1—C7—H7B	109.5	C20—C21—H21	120.7
H7A—C7—H7B	109.5	C20—C19—C18	121.36 (17)
C1—C7—H7C	109.5	C20—C19—H19	119.3
H7A—C7—H7C	109.5	C18—C19—H19	119.3
H7B—C7—H7C	109.5	C21—C22—C23	120.73 (17)
N2—C12—C13	123.75 (15)	C21—C22—H22	119.6
N2—C12—H12	118.1	C23—C22—H22	119.6
C13—C12—H12	118.1

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	2.01	2.8465 (16)	174
O2—H2···N2	0.84	1.96	2.7952 (17)	176
C3—H3···N1	0.95	2.63	3.338 (2)	132

(MRE_TMP_HMB)

Crystal data

C27H38N2O2	Z = 4
Mr = 422.59	F(000) = 920
Monoclinic, P21/c	Dx = 1.156 Mg m^−3
a = 8.356 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 24.894 (12) Å	µ = 0.07 mm^−1
c = 11.744 (6) Å	T = 150 K
β = 96.324 (6)°	Block, colorless
V = 2428 (2) Å^3	0.32 × 0.22 × 0.15 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	4057 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.075
profile data from ω–scans	θmax = 27.6°, θmin = 1.6°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −10→10
Tmin = 0.802, Tmax = 1.000	k = −32→32
25296 measured reflections	l = −15→15
5587 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)] = 0.068	H-atom parameters constrained
wR(F^2) = 0.222	w = 1/[σ^2(Fo^2) + (0.1123P)^2 + 0.443P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.036
5587 reflections	Δρmax = 0.47 e Å^−3
293 parameters	Δρmin = −0.43 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O2	0.30651 (18)	0.52932 (5)	0.75979 (14)	0.0435 (4)
H2	0.3680	0.5032	0.7518	0.065*
O1	0.30666 (18)	0.71790 (5)	0.79072 (13)	0.0411 (4)
H1	0.3679	0.7446	0.7893	0.062*
N1	0.5394 (2)	0.92762 (6)	0.76225 (13)	0.0338 (4)
C1	0.3070 (2)	0.62338 (7)	0.77591 (15)	0.0293 (4)
C2	0.3931 (2)	0.67175 (7)	0.78050 (15)	0.0315 (4)
N2	0.4597 (2)	0.82013 (6)	0.77665 (13)	0.0326 (4)
C5	0.5581 (3)	0.57599 (9)	0.75970 (17)	0.0419 (5)
H5	0.6144	0.5433	0.7519	0.050*
C6	0.3930 (2)	0.57588 (7)	0.76433 (15)	0.0327 (4)
C8	0.4084 (2)	0.84878 (7)	0.68288 (16)	0.0311 (4)
C3	0.5586 (3)	0.67256 (9)	0.77671 (18)	0.0432 (5)
H3	0.6153	0.7057	0.7810	0.052*
C19	0.9605 (2)	0.42856 (7)	0.73126 (17)	0.0339 (4)
C9	0.4489 (2)	0.90329 (7)	0.67595 (15)	0.0315 (4)
C12	0.3074 (3)	0.82070 (8)	0.58739 (18)	0.0431 (5)
H12A	0.2915	0.7832	0.6088	0.065*
H12B	0.3619	0.8220	0.5177	0.065*
H12C	0.2026	0.8386	0.5733	0.065*
C11	0.5503 (2)	0.84439 (7)	0.86316 (16)	0.0331 (4)
C16	1.0408 (2)	0.31940 (7)	0.73260 (18)	0.0345 (4)
C14	0.6918 (3)	0.92722 (9)	0.95104 (18)	0.0456 (5)
H14A	0.7133	0.9640	0.9272	0.068*
H14B	0.7939	0.9080	0.9687	0.068*
H14C	0.6341	0.9282	1.0193	0.068*
C18	0.9067 (2)	0.39624 (8)	0.63709 (17)	0.0349 (4)
C17	0.9466 (2)	0.34154 (8)	0.63786 (17)	0.0350 (4)
C10	0.5907 (2)	0.89883 (7)	0.85598 (16)	0.0322 (4)
C7	0.1293 (3)	0.62248 (7)	0.7849 (2)	0.0404 (5)
H7A	0.0708	0.6194	0.7081	0.061*
H7B	0.0977	0.6558	0.8210	0.061*
H7C	0.1032	0.5917	0.8314	0.061*
C20	1.0544 (2)	0.40665 (8)	0.82584 (16)	0.0340 (4)
C21	1.0941 (2)	0.35174 (8)	0.82688 (17)	0.0354 (4)
C15	0.6046 (3)	0.81133 (9)	0.96716 (19)	0.0488 (6)
H15A	0.5689	0.7741	0.9543	0.073*
H15B	0.5581	0.8260	1.0336	0.073*
H15C	0.7224	0.8123	0.9814	0.073*
C13	0.3930 (3)	0.93641 (8)	0.57152 (18)	0.0475 (6)
H13A	0.4263	0.9738	0.5848	0.071*
H13B	0.2754	0.9346	0.5568	0.071*
H13C	0.4410	0.9223	0.5052	0.071*
C22	1.0830 (3)	0.26012 (8)	0.7346 (2)	0.0556 (6)
H22A	1.1796	0.2541	0.7884	0.083*
H22B	1.1035	0.2486	0.6578	0.083*
H22C	0.9932	0.2394	0.7591	0.083*
C25	0.9171 (3)	0.48773 (8)	0.7289 (2)	0.0535 (6)
H25A	0.9041	0.4999	0.8067	0.080*
H25B	0.8161	0.4932	0.6794	0.080*
H25C	1.0032	0.5084	0.6990	0.080*
C24	0.8073 (3)	0.42103 (11)	0.5345 (2)	0.0580 (7)
H24A	0.7155	0.4403	0.5601	0.087*
H24B	0.7681	0.3926	0.4807	0.087*
H24C	0.8742	0.4462	0.4963	0.087*
C4	0.6403 (3)	0.62487 (9)	0.76662 (19)	0.0473 (6)
H4	0.7536	0.6253	0.7644	0.057*
C27	1.1916 (3)	0.32755 (10)	0.9308 (2)	0.0594 (7)
H27A	1.1301	0.2984	0.9615	0.089*
H27B	1.2147	0.3553	0.9895	0.089*
H27C	1.2930	0.3133	0.9085	0.089*
C26	1.1144 (3)	0.44211 (10)	0.9268 (2)	0.0529 (6)
H26A	1.1266	0.4790	0.9002	0.079*
H26B	1.2187	0.4288	0.9619	0.079*
H26C	1.0367	0.4414	0.9835	0.079*
C23	0.8866 (3)	0.30550 (10)	0.5373 (2)	0.0548 (6)
H23A	0.9669	0.3045	0.4825	0.082*
H23B	0.7850	0.3197	0.4995	0.082*
H23C	0.8692	0.2691	0.5652	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0460 (9)	0.0255 (7)	0.0604 (10)	0.0073 (6)	0.0121 (7)	0.0010 (6)
O1	0.0457 (8)	0.0254 (7)	0.0531 (9)	−0.0068 (6)	0.0099 (7)	−0.0015 (6)
N1	0.0428 (9)	0.0282 (8)	0.0315 (8)	−0.0060 (7)	0.0090 (7)	−0.0028 (6)
C1	0.0326 (9)	0.0285 (9)	0.0269 (9)	−0.0015 (7)	0.0039 (7)	0.0013 (7)
C2	0.0363 (10)	0.0328 (9)	0.0257 (9)	−0.0035 (7)	0.0047 (7)	0.0005 (7)
N2	0.0410 (9)	0.0268 (8)	0.0307 (8)	−0.0048 (7)	0.0071 (7)	−0.0025 (6)
C5	0.0378 (11)	0.0513 (12)	0.0373 (11)	0.0123 (9)	0.0076 (8)	0.0039 (9)
C6	0.0393 (11)	0.0312 (9)	0.0280 (9)	0.0038 (8)	0.0056 (7)	0.0025 (7)
C8	0.0364 (10)	0.0297 (9)	0.0285 (9)	−0.0054 (8)	0.0090 (7)	−0.0058 (7)
C3	0.0401 (12)	0.0505 (12)	0.0393 (11)	−0.0136 (9)	0.0058 (9)	−0.0039 (9)
C19	0.0334 (10)	0.0254 (9)	0.0443 (11)	−0.0009 (7)	0.0108 (8)	−0.0007 (8)
C9	0.0380 (10)	0.0285 (9)	0.0292 (9)	−0.0025 (7)	0.0084 (8)	−0.0005 (7)
C12	0.0525 (13)	0.0397 (11)	0.0362 (11)	−0.0117 (9)	0.0012 (9)	−0.0061 (8)
C11	0.0393 (10)	0.0306 (9)	0.0299 (9)	−0.0050 (8)	0.0067 (8)	−0.0013 (7)
C16	0.0324 (10)	0.0267 (9)	0.0457 (11)	0.0000 (7)	0.0108 (8)	0.0007 (8)
C14	0.0577 (14)	0.0417 (11)	0.0364 (11)	−0.0128 (10)	0.0007 (10)	−0.0041 (9)
C18	0.0339 (10)	0.0362 (10)	0.0347 (10)	−0.0007 (8)	0.0043 (8)	0.0050 (8)
C17	0.0364 (10)	0.0338 (10)	0.0359 (10)	−0.0055 (8)	0.0088 (8)	−0.0057 (8)
C10	0.0387 (10)	0.0290 (9)	0.0302 (9)	−0.0044 (8)	0.0090 (8)	−0.0027 (7)
C7	0.0360 (11)	0.0264 (9)	0.0600 (14)	−0.0013 (8)	0.0106 (9)	−0.0009 (9)
C20	0.0340 (10)	0.0340 (10)	0.0353 (10)	−0.0058 (8)	0.0094 (8)	−0.0046 (8)
C21	0.0302 (10)	0.0356 (10)	0.0410 (11)	−0.0027 (8)	0.0066 (8)	0.0070 (8)
C15	0.0684 (16)	0.0370 (11)	0.0390 (12)	−0.0047 (10)	−0.0030 (10)	0.0061 (9)
C13	0.0682 (16)	0.0369 (11)	0.0368 (11)	−0.0046 (10)	0.0028 (10)	0.0061 (9)
C22	0.0543 (14)	0.0299 (10)	0.0844 (18)	0.0075 (10)	0.0161 (13)	0.0007 (11)
C25	0.0536 (14)	0.0299 (10)	0.0783 (17)	0.0070 (10)	0.0133 (12)	−0.0005 (11)
C24	0.0594 (16)	0.0596 (15)	0.0515 (14)	0.0014 (12)	−0.0089 (12)	0.0137 (11)
C4	0.0300 (10)	0.0716 (16)	0.0409 (12)	−0.0014 (10)	0.0069 (9)	0.0022 (10)
C27	0.0571 (16)	0.0592 (15)	0.0579 (15)	−0.0019 (12)	−0.0111 (12)	0.0160 (12)
C26	0.0593 (15)	0.0559 (14)	0.0432 (13)	−0.0106 (12)	0.0046 (11)	−0.0133 (10)
C23	0.0673 (16)	0.0492 (13)	0.0475 (13)	−0.0117 (12)	0.0042 (11)	−0.0159 (11)

Geometric parameters (Å, º)

O2—C6	1.364 (2)	C18—C17	1.402 (3)
O2—H2	0.8400	C18—C24	1.518 (3)
O1—C2	1.369 (2)	C17—C23	1.523 (3)
O1—H1	0.8400	C7—H7A	0.9800
N1—C9	1.340 (2)	C7—H7B	0.9800
N1—C10	1.344 (2)	C7—H7C	0.9800
C1—C6	1.398 (3)	C20—C21	1.406 (3)
C1—C2	1.400 (2)	C20—C26	1.519 (3)
C1—C7	1.501 (3)	C21—C27	1.515 (3)
C2—C3	1.389 (3)	C15—H15A	0.9800
N2—C8	1.342 (2)	C15—H15B	0.9800
N2—C11	1.342 (2)	C15—H15C	0.9800
C5—C6	1.386 (3)	C13—H13A	0.9800
C5—C4	1.395 (3)	C13—H13B	0.9800
C5—H5	0.9500	C13—H13C	0.9800
C8—C9	1.403 (3)	C22—H22A	0.9800
C8—C12	1.500 (3)	C22—H22B	0.9800
C3—C4	1.381 (3)	C22—H22C	0.9800
C3—H3	0.9500	C25—H25A	0.9800
C19—C20	1.398 (3)	C25—H25B	0.9800
C19—C18	1.401 (3)	C25—H25C	0.9800
C19—C25	1.516 (3)	C24—H24A	0.9800
C9—C13	1.509 (3)	C24—H24B	0.9800
C12—H12A	0.9800	C24—H24C	0.9800
C12—H12B	0.9800	C4—H4	0.9500
C12—H12C	0.9800	C27—H27A	0.9800
C11—C10	1.401 (3)	C27—H27B	0.9800
C11—C15	1.501 (3)	C27—H27C	0.9800
C16—C21	1.401 (3)	C26—H26A	0.9800
C16—C17	1.403 (3)	C26—H26B	0.9800
C16—C22	1.517 (3)	C26—H26C	0.9800
C14—C10	1.500 (3)	C23—H23A	0.9800
C14—H14A	0.9800	C23—H23B	0.9800
C14—H14B	0.9800	C23—H23C	0.9800
C14—H14C	0.9800
C6—O2—H2	109.5	H7A—C7—H7C	109.5
C2—O1—H1	109.5	H7B—C7—H7C	109.5
C9—N1—C10	118.75 (16)	C19—C20—C21	119.81 (17)
C6—C1—C2	117.65 (18)	C19—C20—C26	120.13 (18)
C6—C1—C7	121.17 (16)	C21—C20—C26	120.06 (19)
C2—C1—C7	121.18 (16)	C16—C21—C20	119.84 (18)
O1—C2—C3	121.81 (17)	C16—C21—C27	120.24 (19)
O1—C2—C1	116.85 (17)	C20—C21—C27	119.92 (19)
C3—C2—C1	121.33 (18)	C11—C15—H15A	109.5
C8—N2—C11	118.99 (16)	C11—C15—H15B	109.5
C6—C5—C4	119.00 (19)	H15A—C15—H15B	109.5
C6—C5—H5	120.5	C11—C15—H15C	109.5
C4—C5—H5	120.5	H15A—C15—H15C	109.5
O2—C6—C5	121.69 (17)	H15B—C15—H15C	109.5
O2—C6—C1	116.54 (17)	C9—C13—H13A	109.5
C5—C6—C1	121.76 (18)	C9—C13—H13B	109.5
N2—C8—C9	120.29 (16)	H13A—C13—H13B	109.5
N2—C8—C12	117.92 (16)	C9—C13—H13C	109.5
C9—C8—C12	121.79 (17)	H13A—C13—H13C	109.5
C4—C3—C2	119.56 (19)	H13B—C13—H13C	109.5
C4—C3—H3	120.2	C16—C22—H22A	109.5
C2—C3—H3	120.2	C16—C22—H22B	109.5
C20—C19—C18	120.41 (17)	H22A—C22—H22B	109.5
C20—C19—C25	120.37 (19)	C16—C22—H22C	109.5
C18—C19—C25	119.21 (19)	H22A—C22—H22C	109.5
N1—C9—C8	120.84 (17)	H22B—C22—H22C	109.5
N1—C9—C13	117.78 (17)	C19—C25—H25A	109.5
C8—C9—C13	121.37 (17)	C19—C25—H25B	109.5
C8—C12—H12A	109.5	H25A—C25—H25B	109.5
C8—C12—H12B	109.5	C19—C25—H25C	109.5
H12A—C12—H12B	109.5	H25A—C25—H25C	109.5
C8—C12—H12C	109.5	H25B—C25—H25C	109.5
H12A—C12—H12C	109.5	C18—C24—H24A	109.5
H12B—C12—H12C	109.5	C18—C24—H24B	109.5
N2—C11—C10	120.62 (17)	H24A—C24—H24B	109.5
N2—C11—C15	117.65 (17)	C18—C24—H24C	109.5
C10—C11—C15	121.73 (17)	H24A—C24—H24C	109.5
C21—C16—C17	120.17 (17)	H24B—C24—H24C	109.5
C21—C16—C22	119.57 (19)	C3—C4—C5	120.7 (2)
C17—C16—C22	120.26 (19)	C3—C4—H4	119.7
C10—C14—H14A	109.5	C5—C4—H4	119.7
C10—C14—H14B	109.5	C21—C27—H27A	109.5
H14A—C14—H14B	109.5	C21—C27—H27B	109.5
C10—C14—H14C	109.5	H27A—C27—H27B	109.5
H14A—C14—H14C	109.5	C21—C27—H27C	109.5
H14B—C14—H14C	109.5	H27A—C27—H27C	109.5
C19—C18—C17	119.84 (17)	H27B—C27—H27C	109.5
C19—C18—C24	119.56 (19)	C20—C26—H26A	109.5
C17—C18—C24	120.60 (19)	C20—C26—H26B	109.5
C18—C17—C16	119.93 (17)	H26A—C26—H26B	109.5
C18—C17—C23	120.64 (19)	C20—C26—H26C	109.5
C16—C17—C23	119.43 (18)	H26A—C26—H26C	109.5
N1—C10—C11	120.51 (17)	H26B—C26—H26C	109.5
N1—C10—C14	117.46 (17)	C17—C23—H23A	109.5
C11—C10—C14	122.03 (17)	C17—C23—H23B	109.5
C1—C7—H7A	109.5	H23A—C23—H23B	109.5
C1—C7—H7B	109.5	C17—C23—H23C	109.5
H7A—C7—H7B	109.5	H23A—C23—H23C	109.5
C1—C7—H7C	109.5	H23B—C23—H23C	109.5
C6—C1—C2—O1	179.38 (16)	C24—C18—C17—C16	178.9 (2)
C7—C1—C2—O1	−1.5 (3)	C19—C18—C17—C23	178.82 (19)
C6—C1—C2—C3	−1.6 (3)	C24—C18—C17—C23	−1.9 (3)
C7—C1—C2—C3	177.47 (18)	C21—C16—C17—C18	0.5 (3)
C4—C5—C6—O2	−178.96 (18)	C22—C16—C17—C18	179.35 (19)
C4—C5—C6—C1	−0.1 (3)	C21—C16—C17—C23	−178.63 (18)
C2—C1—C6—O2	−179.85 (16)	C22—C16—C17—C23	0.2 (3)
C7—C1—C6—O2	1.0 (3)	C9—N1—C10—C11	0.0 (3)
C2—C1—C6—C5	1.2 (3)	C9—N1—C10—C14	179.99 (18)
C7—C1—C6—C5	−177.88 (18)	N2—C11—C10—N1	0.0 (3)
C11—N2—C8—C9	−0.2 (3)	C15—C11—C10—N1	−179.43 (19)
C11—N2—C8—C12	179.97 (18)	N2—C11—C10—C14	179.99 (19)
O1—C2—C3—C4	179.83 (18)	C15—C11—C10—C14	0.6 (3)
C1—C2—C3—C4	0.9 (3)	C18—C19—C20—C21	−0.5 (3)
C10—N1—C9—C8	−0.1 (3)	C25—C19—C20—C21	−179.83 (18)
C10—N1—C9—C13	−179.86 (17)	C18—C19—C20—C26	179.05 (18)
N2—C8—C9—N1	0.2 (3)	C25—C19—C20—C26	−0.3 (3)
C12—C8—C9—N1	180.00 (18)	C17—C16—C21—C20	−0.7 (3)
N2—C8—C9—C13	179.95 (19)	C22—C16—C21—C20	−179.55 (19)
C12—C8—C9—C13	−0.2 (3)	C17—C16—C21—C27	178.1 (2)
C8—N2—C11—C10	0.1 (3)	C22—C16—C21—C27	−0.7 (3)
C8—N2—C11—C15	179.55 (18)	C19—C20—C21—C16	0.7 (3)
C20—C19—C18—C17	0.3 (3)	C26—C20—C21—C16	−178.86 (19)
C25—C19—C18—C17	179.65 (19)	C19—C20—C21—C27	−178.1 (2)
C20—C19—C18—C24	−178.95 (19)	C26—C20—C21—C27	2.3 (3)
C25—C19—C18—C24	0.4 (3)	C2—C3—C4—C5	0.3 (3)
C19—C18—C17—C16	−0.3 (3)	C6—C5—C4—C3	−0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1^i	0.84	2.05	2.865 (2)	164
O1—H1···N2	0.84	2.04	2.861 (2)	165

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

(MRE_TMP_PER)

Crystal data

C50H52N4O4	V = 1028.8 (3) Å^3
Mr = 772.95	Z = 1
Triclinic, P1	F(000) = 412
a = 7.5460 (9) Å	Dx = 1.248 Mg m^−3
b = 9.4647 (16) Å	Mo Kα radiation, λ = 0.71073 Å
c = 14.8318 (19) Å	µ = 0.08 mm^−1
α = 85.58 (2)°	T = 150 K
β = 77.14 (2)°	Block, yellow
γ = 86.77 (3)°	0.47 × 0.29 × 0.18 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3277 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.077
profile data from ω–scans	θmax = 27.6°, θmin = 1.4°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.638, Tmax = 1.000	k = −12→12
11018 measured reflections	l = −19→19
4739 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)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.235	w = 1/[σ^2(Fo^2) + (0.1669P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
4739 reflections	Δρmax = 0.31 e Å^−3
269 parameters	Δρmin = −0.33 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O2	−0.0730 (2)	0.29530 (16)	0.28109 (11)	0.0596 (4)
H2	−0.0337	0.2384	0.3191	0.089*
O1	0.0899 (2)	0.70192 (15)	0.08259 (11)	0.0569 (4)
H1	0.1704	0.7625	0.0684	0.085*
N2	0.3590 (2)	−0.09191 (16)	0.01685 (11)	0.0448 (4)
C1	0.0111 (2)	0.49597 (18)	0.18004 (12)	0.0378 (4)
C2	0.1299 (3)	0.60701 (19)	0.15042 (12)	0.0407 (4)
C13	0.3273 (3)	0.04530 (19)	0.03585 (12)	0.0421 (4)
C6	0.0463 (2)	0.40068 (19)	0.25160 (13)	0.0406 (4)
C3	0.2802 (3)	0.6193 (2)	0.18896 (14)	0.0463 (5)
H3	0.3606	0.6944	0.1675	0.056*
C14	0.5299 (3)	−0.13790 (19)	−0.01936 (13)	0.0447 (5)
C5	0.1953 (3)	0.4126 (2)	0.29055 (14)	0.0485 (5)
H5	0.2171	0.3463	0.3388	0.058*
C7	−0.1479 (3)	0.4799 (2)	0.13694 (15)	0.0542 (5)
H7A	−0.1083	0.4272	0.0811	0.081*
H7B	−0.1971	0.5739	0.1202	0.081*
H7C	−0.2423	0.4282	0.1813	0.081*
C21	−0.4225 (2)	−0.0778 (2)	0.42039 (16)	0.0502 (5)
C4	0.3119 (3)	0.5219 (2)	0.25838 (14)	0.0494 (5)
H4	0.4148	0.5301	0.2843	0.059*
C22	−0.4592 (3)	−0.1499 (2)	0.51076 (17)	0.0508 (5)
C12	0.1339 (3)	0.0932 (2)	0.07338 (16)	0.0577 (6)
H12A	0.0583	0.0103	0.0905	0.087*
H12B	0.0895	0.1541	0.0259	0.087*
H12C	0.1274	0.1465	0.1282	0.087*
C20	−0.4629 (3)	0.0702 (2)	0.40807 (15)	0.0510 (5)
C15	0.5598 (4)	−0.2909 (2)	−0.04144 (18)	0.0630 (6)
H15A	0.4443	−0.3388	−0.0226	0.095*
H15B	0.6478	−0.3370	−0.0079	0.095*
H15C	0.6069	−0.2968	−0.1082	0.095*
C16	−0.3456 (3)	−0.1567 (3)	0.3419 (2)	0.0750 (8)
C19	−0.4247 (4)	0.1339 (3)	0.3188 (2)	0.0758 (8)
H19	−0.4501	0.2327	0.3098	0.091*
C18	−0.3504 (4)	0.0569 (6)	0.2422 (2)	0.1019 (12)
H18	−0.3269	0.1039	0.1821	0.122*
C25	−0.3043 (4)	−0.3014 (4)	0.3536 (3)	0.0995 (13)
H25	−0.2504	−0.3532	0.3013	0.119*
C17	−0.3112 (4)	−0.0834 (5)	0.2521 (2)	0.0988 (12)
H17	−0.2602	−0.1341	0.1990	0.119*
N1	−0.0061 (2)	0.89525 (16)	0.57075 (12)	0.0452 (4)
C9	0.0608 (2)	0.8659 (2)	0.48243 (14)	0.0436 (4)
C10	−0.0675 (2)	1.0279 (2)	0.58936 (13)	0.0443 (5)
C8	0.1254 (3)	0.7157 (2)	0.46438 (18)	0.0603 (6)
H8A	0.1054	0.6577	0.5231	0.091*
H8B	0.2554	0.7133	0.4353	0.091*
H8C	0.0575	0.6781	0.4230	0.091*
C11	−0.1446 (4)	1.0561 (3)	0.68812 (16)	0.0641 (6)
H11A	−0.1376	0.9686	0.7273	0.096*
H11B	−0.2721	1.0894	0.6953	0.096*
H11C	−0.0751	1.1289	0.7067	0.096*
C23	−0.4188 (4)	−0.2949 (3)	0.5177 (2)	0.0779 (8)
H23	−0.4449	−0.3447	0.5769	0.094*
C24	−0.3412 (5)	−0.3690 (3)	0.4400 (4)	0.1019 (13)
H24	−0.3135	−0.4678	0.4472	0.122*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0634 (9)	0.0537 (9)	0.0649 (10)	−0.0223 (7)	−0.0242 (8)	0.0208 (7)
O1	0.0667 (10)	0.0479 (9)	0.0582 (9)	−0.0112 (7)	−0.0229 (8)	0.0176 (7)
N2	0.0556 (10)	0.0389 (8)	0.0388 (9)	−0.0041 (7)	−0.0084 (7)	0.0013 (6)
C1	0.0400 (9)	0.0367 (9)	0.0357 (9)	−0.0002 (7)	−0.0062 (7)	−0.0037 (7)
C2	0.0495 (10)	0.0345 (9)	0.0376 (10)	−0.0008 (7)	−0.0091 (8)	−0.0009 (7)
C13	0.0529 (10)	0.0400 (10)	0.0320 (9)	0.0005 (8)	−0.0084 (8)	0.0010 (7)
C6	0.0415 (9)	0.0376 (9)	0.0416 (10)	−0.0030 (7)	−0.0075 (7)	0.0002 (7)
C3	0.0505 (10)	0.0404 (10)	0.0485 (11)	−0.0111 (8)	−0.0106 (9)	−0.0003 (8)
C14	0.0606 (12)	0.0359 (9)	0.0370 (10)	−0.0019 (8)	−0.0106 (8)	0.0006 (7)
C5	0.0529 (11)	0.0482 (11)	0.0457 (11)	−0.0033 (9)	−0.0165 (9)	0.0065 (8)
C7	0.0548 (12)	0.0582 (12)	0.0526 (12)	−0.0083 (10)	−0.0201 (10)	0.0055 (9)
C21	0.0350 (9)	0.0531 (12)	0.0672 (14)	−0.0054 (8)	−0.0172 (9)	−0.0130 (10)
C4	0.0477 (10)	0.0553 (12)	0.0491 (11)	−0.0073 (9)	−0.0180 (9)	−0.0027 (9)
C22	0.0412 (10)	0.0395 (10)	0.0790 (15)	−0.0037 (8)	−0.0292 (10)	−0.0010 (9)
C12	0.0574 (12)	0.0582 (13)	0.0544 (13)	0.0051 (10)	−0.0078 (10)	−0.0015 (10)
C20	0.0405 (10)	0.0537 (12)	0.0626 (13)	−0.0133 (8)	−0.0191 (9)	0.0045 (10)
C15	0.0799 (16)	0.0398 (11)	0.0663 (15)	0.0004 (10)	−0.0082 (12)	−0.0096 (10)
C16	0.0399 (11)	0.096 (2)	0.093 (2)	−0.0062 (12)	−0.0101 (12)	−0.0417 (16)
C19	0.0591 (14)	0.095 (2)	0.0728 (18)	−0.0258 (13)	−0.0181 (13)	0.0235 (15)
C18	0.0685 (18)	0.173 (4)	0.0627 (19)	−0.038 (2)	−0.0088 (15)	0.009 (2)
C25	0.0585 (16)	0.099 (3)	0.154 (4)	0.0195 (16)	−0.035 (2)	−0.077 (3)
C17	0.0591 (16)	0.167 (4)	0.071 (2)	−0.024 (2)	0.0009 (14)	−0.042 (2)
N1	0.0441 (8)	0.0407 (9)	0.0511 (10)	−0.0051 (7)	−0.0140 (7)	0.0078 (7)
C9	0.0383 (9)	0.0405 (10)	0.0526 (12)	−0.0018 (7)	−0.0134 (8)	0.0039 (8)
C10	0.0402 (9)	0.0450 (10)	0.0481 (11)	−0.0050 (8)	−0.0117 (8)	0.0023 (8)
C8	0.0607 (13)	0.0428 (11)	0.0781 (16)	0.0053 (10)	−0.0185 (12)	−0.0032 (10)
C11	0.0713 (15)	0.0695 (15)	0.0504 (13)	−0.0005 (12)	−0.0125 (11)	−0.0021 (11)
C23	0.0826 (17)	0.0453 (13)	0.126 (2)	0.0001 (12)	−0.0676 (17)	−0.0037 (14)
C24	0.083 (2)	0.0577 (17)	0.189 (4)	0.0254 (15)	−0.073 (3)	−0.050 (2)

Geometric parameters (Å, º)

O2—C6	1.362 (2)	C12—H12C	0.9800
O2—H2	0.8400	C20—C19	1.388 (3)
O1—C2	1.370 (2)	C20—C22^ii	1.463 (3)
O1—H1	0.8400	C15—H15A	0.9800
N2—C14	1.344 (3)	C15—H15B	0.9800
N2—C13	1.347 (2)	C15—H15C	0.9800
C1—C2	1.400 (2)	C16—C25	1.394 (5)
C1—C6	1.400 (3)	C16—C17	1.430 (5)
C1—C7	1.500 (3)	C19—C18	1.390 (5)
C2—C3	1.392 (3)	C19—H19	0.9500
C13—C14^i	1.394 (3)	C18—C17	1.348 (6)
C13—C12	1.500 (3)	C18—H18	0.9500
C6—C5	1.387 (3)	C25—C24	1.365 (6)
C3—C4	1.380 (3)	C25—H25	0.9500
C3—H3	0.9500	C17—H17	0.9500
C14—C13^i	1.394 (3)	N1—C9	1.339 (3)
C14—C15	1.503 (3)	N1—C10	1.341 (2)
C5—C4	1.383 (3)	C9—C10^iii	1.401 (3)
C5—H5	0.9500	C9—C8	1.500 (3)
C7—H7A	0.9800	C10—C9^iii	1.401 (3)
C7—H7B	0.9800	C10—C11	1.490 (3)
C7—H7C	0.9800	C8—H8A	0.9800
C21—C20	1.423 (3)	C8—H8B	0.9800
C21—C16	1.426 (3)	C8—H8C	0.9800
C21—C22	1.433 (3)	C11—H11A	0.9800
C4—H4	0.9500	C11—H11B	0.9800
C22—C23	1.389 (3)	C11—H11C	0.9800
C22—C20^ii	1.463 (3)	C23—C24	1.393 (5)
C12—H12A	0.9800	C23—H23	0.9500
C12—H12B	0.9800	C24—H24	0.9500
C6—O2—H2	109.5	C21—C20—C22^ii	119.3 (2)
C2—O1—H1	109.5	C14—C15—H15A	109.5
C14—N2—C13	119.01 (16)	C14—C15—H15B	109.5
C2—C1—C6	117.44 (16)	H15A—C15—H15B	109.5
C2—C1—C7	121.28 (17)	C14—C15—H15C	109.5
C6—C1—C7	121.28 (17)	H15A—C15—H15C	109.5
O1—C2—C3	122.33 (17)	H15B—C15—H15C	109.5
O1—C2—C1	116.62 (16)	C25—C16—C21	120.2 (3)
C3—C2—C1	121.05 (17)	C25—C16—C17	121.4 (3)
N2—C13—C14^i	120.53 (17)	C21—C16—C17	118.4 (3)
N2—C13—C12	117.28 (18)	C20—C19—C18	121.8 (3)
C14^i—C13—C12	122.18 (18)	C20—C19—H19	119.1
O2—C6—C5	121.52 (17)	C18—C19—H19	119.1
O2—C6—C1	116.68 (16)	C17—C18—C19	120.9 (3)
C5—C6—C1	121.80 (17)	C17—C18—H18	119.5
C4—C3—C2	119.78 (18)	C19—C18—H18	119.5
C4—C3—H3	120.1	C24—C25—C16	120.1 (3)
C2—C3—H3	120.1	C24—C25—H25	119.9
N2—C14—C13^i	120.45 (17)	C16—C25—H25	119.9
N2—C14—C15	117.63 (18)	C18—C17—C16	120.6 (3)
C13^i—C14—C15	121.92 (19)	C18—C17—H17	119.7
C4—C5—C6	119.21 (18)	C16—C17—H17	119.7
C4—C5—H5	120.4	C9—N1—C10	118.91 (16)
C6—C5—H5	120.4	N1—C9—C10^iii	120.59 (17)
C1—C7—H7A	109.5	N1—C9—C8	117.27 (18)
C1—C7—H7B	109.5	C10^iii—C9—C8	122.13 (19)
H7A—C7—H7B	109.5	N1—C10—C9^iii	120.50 (18)
C1—C7—H7C	109.5	N1—C10—C11	117.48 (18)
H7A—C7—H7C	109.5	C9^iii—C10—C11	122.01 (19)
H7B—C7—H7C	109.5	C9—C8—H8A	109.5
C20—C21—C16	119.9 (2)	C9—C8—H8B	109.5
C20—C21—C22	121.0 (2)	H8A—C8—H8B	109.5
C16—C21—C22	119.1 (2)	C9—C8—H8C	109.5
C3—C4—C5	120.70 (18)	H8A—C8—H8C	109.5
C3—C4—H4	119.6	H8B—C8—H8C	109.5
C5—C4—H4	119.6	C10—C11—H11A	109.5
C23—C22—C21	118.1 (2)	C10—C11—H11B	109.5
C23—C22—C20^ii	122.3 (2)	H11A—C11—H11B	109.5
C21—C22—C20^ii	119.65 (18)	C10—C11—H11C	109.5
C13—C12—H12A	109.5	H11A—C11—H11C	109.5
C13—C12—H12B	109.5	H11B—C11—H11C	109.5
H12A—C12—H12B	109.5	C22—C23—C24	121.7 (3)
C13—C12—H12C	109.5	C22—C23—H23	119.2
H12A—C12—H12C	109.5	C24—C23—H23	119.2
H12B—C12—H12C	109.5	C25—C24—C23	120.9 (3)
C19—C20—C21	118.3 (2)	C25—C24—H24	119.6
C19—C20—C22^ii	122.4 (2)	C23—C24—H24	119.6

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

(MRE_TMP_PHE)

Crystal data

C42H48N6O4	V = 937.9 (15) Å^3
Mr = 700.86	Z = 1
Triclinic, P1	F(000) = 374
a = 7.324 (7) Å	Dx = 1.241 Mg m^−3
b = 8.723 (8) Å	Mo Kα radiation, λ = 0.71073 Å
c = 15.107 (14) Å	µ = 0.08 mm^−1
α = 82.27 (3)°	T = 150 K
β = 88.73 (3)°	Block, green
γ = 78.76 (2)°	0.42 × 0.33 × 0.22 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3005 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.069
profile data from ω–scans	θmax = 27.6°, θmin = 1.4°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.691, Tmax = 1.000	k = −11→11
10049 measured reflections	l = −19→19
4317 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)] = 0.065	w = 1/[σ^2(Fo^2) + (0.1106P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.213	(Δ/σ)max = 0.006
S = 1.09	Δρmax = 0.37 e Å^−3
4317 reflections	Δρmin = −0.33 e Å^−3
243 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.029 (8)

Special details

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

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

	x	y	z	Uiso*/Ueq
N2	0.1466 (3)	0.0760 (2)	0.98171 (11)	0.0322 (4)
N1	0.5019 (2)	0.8892 (2)	0.57422 (12)	0.0300 (4)
C1	0.5012 (3)	0.4591 (2)	0.82893 (13)	0.0273 (5)
O1	0.5882 (2)	0.6646 (2)	0.72968 (11)	0.0424 (5)
H1	0.5541	0.7239	0.6820	0.064*
C6	0.3714 (3)	0.3644 (2)	0.85518 (13)	0.0286 (5)
O2	0.4187 (2)	0.2547 (2)	0.92842 (11)	0.0447 (5)
H2	0.3277	0.2116	0.9436	0.067*
C13	0.4359 (3)	1.0426 (2)	0.57943 (14)	0.0286 (5)
C5	0.2052 (3)	0.3810 (3)	0.80906 (15)	0.0336 (5)
H5	0.1185	0.3154	0.8281	0.040*
C2	0.4594 (3)	0.5723 (2)	0.75378 (14)	0.0292 (5)
C14	0.5656 (3)	0.8448 (2)	0.49587 (14)	0.0291 (5)
C3	0.2934 (3)	0.5902 (3)	0.70661 (15)	0.0339 (5)
H3	0.2670	0.6674	0.6555	0.041*
C4	0.1676 (3)	0.4948 (3)	0.73480 (15)	0.0347 (5)
H4	0.0540	0.5072	0.7030	0.042*
C9	0.1446 (3)	−0.0581 (2)	0.94847 (14)	0.0315 (5)
C10	0.0050 (3)	0.1351 (2)	1.03307 (14)	0.0326 (5)
C7	0.6781 (3)	0.4409 (3)	0.88123 (15)	0.0378 (6)
H7A	0.7660	0.4948	0.8456	0.057*
H7B	0.7330	0.3286	0.8954	0.057*
H7C	0.6505	0.4873	0.9368	0.057*
C15	0.6392 (4)	0.6727 (3)	0.49356 (18)	0.0438 (6)
H15A	0.7756	0.6525	0.4945	0.066*
H15B	0.5962	0.6415	0.4389	0.066*
H15C	0.5940	0.6115	0.5458	0.066*
C12	0.3654 (3)	1.0870 (3)	0.66817 (16)	0.0422 (6)
H12A	0.3986	0.9957	0.7142	0.063*
H12B	0.2297	1.1208	0.6655	0.063*
H12C	0.4218	1.1735	0.6829	0.063*
C8	0.3065 (4)	−0.1218 (3)	0.89335 (17)	0.0465 (6)
H8A	0.3919	−0.0474	0.8852	0.070*
H8B	0.2620	−0.1364	0.8349	0.070*
H8C	0.3719	−0.2233	0.9238	0.070*
C11	0.0164 (4)	0.2848 (3)	1.06947 (18)	0.0484 (7)
H11A	0.0580	0.2600	1.1319	0.073*
H11B	−0.1066	0.3540	1.0661	0.073*
H11C	0.1053	0.3381	1.0342	0.073*
N3	−0.0140 (3)	0.1569 (2)	0.45628 (13)	0.0355 (5)
C18	0.0512 (3)	0.0311 (3)	0.41381 (15)	0.0333 (5)
C20	−0.0657 (3)	0.1263 (3)	0.54167 (15)	0.0332 (5)
C17	0.1064 (3)	0.0555 (3)	0.32313 (16)	0.0435 (6)
H17	0.0979	0.1597	0.2932	0.052*
C21	−0.1360 (3)	0.2549 (3)	0.59042 (18)	0.0452 (6)
H21	−0.1477	0.3603	0.5620	0.054*
C16	0.1715 (4)	−0.0704 (4)	0.27911 (18)	0.0515 (7)
H16	0.2076	−0.0533	0.2184	0.062*
C22	−0.1861 (3)	0.2266 (4)	0.67729 (19)	0.0523 (7)
H22	−0.2315	0.3128	0.7093	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N2	0.0425 (10)	0.0294 (10)	0.0261 (9)	−0.0150 (8)	−0.0005 (8)	0.0034 (7)
N1	0.0336 (9)	0.0273 (9)	0.0281 (9)	−0.0083 (7)	0.0029 (7)	0.0034 (7)
C1	0.0313 (10)	0.0254 (10)	0.0256 (10)	−0.0083 (8)	0.0014 (8)	−0.0011 (8)
O1	0.0432 (9)	0.0430 (10)	0.0395 (10)	−0.0200 (8)	−0.0030 (7)	0.0174 (7)
C6	0.0337 (11)	0.0273 (11)	0.0257 (10)	−0.0106 (9)	0.0008 (8)	0.0003 (8)
O2	0.0480 (10)	0.0451 (10)	0.0418 (10)	−0.0263 (8)	−0.0087 (8)	0.0177 (8)
C13	0.0291 (10)	0.0274 (11)	0.0290 (11)	−0.0065 (8)	0.0018 (8)	−0.0010 (8)
C5	0.0339 (11)	0.0328 (12)	0.0373 (12)	−0.0144 (9)	0.0025 (9)	−0.0056 (9)
C2	0.0333 (11)	0.0247 (10)	0.0294 (11)	−0.0080 (9)	0.0042 (9)	0.0001 (8)
C14	0.0310 (10)	0.0238 (10)	0.0321 (11)	−0.0065 (8)	0.0025 (8)	−0.0008 (8)
C3	0.0389 (12)	0.0299 (11)	0.0300 (11)	−0.0039 (9)	−0.0023 (9)	0.0028 (9)
C4	0.0312 (11)	0.0366 (12)	0.0363 (12)	−0.0046 (9)	−0.0045 (9)	−0.0067 (10)
C9	0.0462 (12)	0.0265 (11)	0.0214 (10)	−0.0109 (9)	0.0016 (9)	0.0032 (8)
C10	0.0504 (13)	0.0246 (11)	0.0242 (11)	−0.0138 (10)	−0.0028 (9)	0.0013 (8)
C7	0.0385 (12)	0.0406 (13)	0.0348 (12)	−0.0160 (10)	−0.0041 (10)	0.0056 (10)
C15	0.0519 (14)	0.0231 (11)	0.0548 (16)	−0.0041 (10)	0.0016 (12)	−0.0043 (10)
C12	0.0445 (13)	0.0504 (15)	0.0309 (12)	−0.0066 (11)	0.0062 (10)	−0.0077 (10)
C8	0.0572 (15)	0.0459 (15)	0.0344 (13)	−0.0087 (12)	0.0118 (11)	−0.0021 (11)
C11	0.0749 (18)	0.0320 (13)	0.0439 (15)	−0.0219 (13)	−0.0012 (13)	−0.0076 (11)
N3	0.0351 (10)	0.0298 (10)	0.0391 (11)	−0.0022 (8)	−0.0058 (8)	−0.0008 (8)
C18	0.0303 (11)	0.0338 (12)	0.0347 (12)	−0.0044 (9)	−0.0048 (9)	−0.0025 (9)
C20	0.0287 (10)	0.0305 (11)	0.0385 (13)	−0.0002 (9)	−0.0075 (9)	−0.0042 (9)
C17	0.0391 (12)	0.0524 (15)	0.0368 (13)	−0.0080 (11)	−0.0055 (10)	0.0015 (11)
C21	0.0398 (12)	0.0366 (14)	0.0576 (17)	0.0025 (11)	−0.0064 (12)	−0.0133 (12)
C16	0.0419 (13)	0.075 (2)	0.0375 (14)	−0.0081 (13)	0.0018 (11)	−0.0128 (14)
C22	0.0393 (13)	0.0669 (19)	0.0529 (16)	−0.0003 (13)	0.0003 (12)	−0.0305 (14)

Geometric parameters (Å, º)

N2—C9	1.336 (3)	C7—H7C	0.9800
N2—C10	1.344 (3)	C15—H15A	0.9800
N1—C14	1.340 (3)	C15—H15B	0.9800
N1—C13	1.344 (3)	C15—H15C	0.9800
C1—C6	1.395 (3)	C12—H12A	0.9800
C1—C2	1.397 (3)	C12—H12B	0.9800
C1—C7	1.503 (3)	C12—H12C	0.9800
O1—C2	1.368 (3)	C8—H8A	0.9800
O1—H1	0.8400	C8—H8B	0.9800
C6—O2	1.365 (3)	C8—H8C	0.9800
C6—C5	1.389 (3)	C11—H11A	0.9800
O2—H2	0.8400	C11—H11B	0.9800
C13—C14^i	1.398 (3)	C11—H11C	0.9800
C13—C12	1.498 (3)	N3—C20	1.343 (3)
C5—C4	1.388 (3)	N3—C18	1.347 (3)
C5—H5	0.9500	C18—C17	1.420 (4)
C2—C3	1.395 (3)	C18—C20^iii	1.431 (3)
C14—C13^i	1.398 (3)	C20—C21	1.430 (3)
C14—C15	1.498 (3)	C20—C18^iii	1.431 (3)
C3—C4	1.382 (3)	C17—C16	1.362 (4)
C3—H3	0.9500	C17—H17	0.9500
C4—H4	0.9500	C21—C22	1.358 (4)
C9—C10^ii	1.397 (3)	C21—H21	0.9500
C9—C8	1.494 (3)	C16—C22^iii	1.416 (5)
C10—C9^ii	1.397 (3)	C16—H16	0.9500
C10—C11	1.500 (3)	C22—C16^iii	1.416 (5)
C7—H7A	0.9800	C22—H22	0.9500
C7—H7B	0.9800
C9—N2—C10	119.65 (19)	H15A—C15—H15B	109.5
C14—N1—C13	119.33 (17)	C14—C15—H15C	109.5
C6—C1—C2	117.78 (19)	H15A—C15—H15C	109.5
C6—C1—C7	120.61 (18)	H15B—C15—H15C	109.5
C2—C1—C7	121.60 (19)	C13—C12—H12A	109.5
C2—O1—H1	109.5	C13—C12—H12B	109.5
O2—C6—C5	122.45 (19)	H12A—C12—H12B	109.5
O2—C6—C1	115.78 (19)	C13—C12—H12C	109.5
C5—C6—C1	121.77 (19)	H12A—C12—H12C	109.5
C6—O2—H2	109.5	H12B—C12—H12C	109.5
N1—C13—C14^i	120.48 (19)	C9—C8—H8A	109.5
N1—C13—C12	117.57 (19)	C9—C8—H8B	109.5
C14^i—C13—C12	122.0 (2)	H8A—C8—H8B	109.5
C4—C5—C6	119.1 (2)	C9—C8—H8C	109.5
C4—C5—H5	120.5	H8A—C8—H8C	109.5
C6—C5—H5	120.5	H8B—C8—H8C	109.5
O1—C2—C3	122.06 (19)	C10—C11—H11A	109.5
O1—C2—C1	116.76 (19)	C10—C11—H11B	109.5
C3—C2—C1	121.18 (19)	H11A—C11—H11B	109.5
N1—C14—C13^i	120.2 (2)	C10—C11—H11C	109.5
N1—C14—C15	117.37 (19)	H11A—C11—H11C	109.5
C13^i—C14—C15	122.4 (2)	H11B—C11—H11C	109.5
C4—C3—C2	119.5 (2)	C20—N3—C18	116.5 (2)
C4—C3—H3	120.3	N3—C18—C17	119.3 (2)
C2—C3—H3	120.3	N3—C18—C20^iii	121.2 (2)
C3—C4—C5	120.7 (2)	C17—C18—C20^iii	119.5 (2)
C3—C4—H4	119.6	N3—C20—C21	119.2 (2)
C5—C4—H4	119.6	N3—C20—C18^iii	122.2 (2)
N2—C9—C10^ii	119.8 (2)	C21—C20—C18^iii	118.6 (2)
N2—C9—C8	118.0 (2)	C16—C17—C18	120.0 (3)
C10^ii—C9—C8	122.2 (2)	C16—C17—H17	120.0
N2—C10—C9^ii	120.6 (2)	C18—C17—H17	120.0
N2—C10—C11	117.2 (2)	C22—C21—C20	120.2 (3)
C9^ii—C10—C11	122.3 (2)	C22—C21—H21	119.9
C1—C7—H7A	109.5	C20—C21—H21	119.9
C1—C7—H7B	109.5	C17—C16—C22^iii	120.9 (3)
H7A—C7—H7B	109.5	C17—C16—H16	119.6
C1—C7—H7C	109.5	C22^iii—C16—H16	119.6
H7A—C7—H7C	109.5	C21—C22—C16^iii	120.9 (3)
H7B—C7—H7C	109.5	C21—C22—H22	119.5
C14—C15—H15A	109.5	C16^iii—C22—H22	119.5
C14—C15—H15B	109.5

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	2.01	2.845 (3)	170
O2—H2···N2	0.84	1.97	2.802 (3)	170
C8—H8C···O2^iv	0.98	2.69	3.337 (4)	124
O1—H1···N1	0.84	2.01	2.845 (3)	170
O2—H2···N2	0.84	1.97	2.802 (3)	170
C8—H8C···O2^iv	0.98	2.69	3.337 (4)	124

Symmetry code: (iv) −x+1, −y, −z+2.

(MRE_TMP_PYR)

Crystal data

C31H30N2O2	Z = 4
Mr = 462.57	F(000) = 984
Monoclinic, P21/c	Dx = 1.275 Mg m^−3
a = 8.0059 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 24.903 (2) Å	µ = 0.08 mm^−1
c = 12.0892 (9) Å	T = 150 K
β = 91.065 (3)°	Block, colorless
V = 2409.8 (3) Å^3	0.51 × 0.30 × 0.21 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	4725 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.103
profile data from ω–scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −10→10
Tmin = 0.815, Tmax = 1.000	k = −32→32
24699 measured reflections	l = −15→15
5522 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)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.189	w = 1/[σ^2(Fo^2) + (0.0909P)^2 + 0.7193P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
5522 reflections	Δρmax = 0.56 e Å^−3
323 parameters	Δρmin = −0.42 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.34984 (16)	0.03262 (5)	0.22959 (13)	0.0418 (3)
H1	0.4149	0.0065	0.2397	0.063*
N1	0.47068 (18)	0.32166 (5)	0.22536 (12)	0.0276 (3)
O2	0.33567 (16)	0.21946 (5)	0.19309 (12)	0.0373 (3)
H2	0.3940	0.2471	0.2034	0.056*
N3	0.50755 (17)	0.43177 (5)	0.23728 (11)	0.0268 (3)
C8	0.5373 (2)	0.34890 (6)	0.14126 (13)	0.0260 (3)
C11	0.4232 (2)	0.34868 (6)	0.31565 (13)	0.0263 (3)
C9	0.5562 (2)	0.40471 (6)	0.14752 (13)	0.0266 (3)
C6	0.4304 (2)	0.17498 (6)	0.21339 (13)	0.0276 (3)
C2	0.4388 (2)	0.07922 (6)	0.23217 (13)	0.0286 (4)
C12	0.5896 (2)	0.31753 (7)	0.04171 (15)	0.0373 (4)
H12A	0.5644	0.2794	0.0528	0.056*
H12B	0.7099	0.3220	0.0312	0.056*
H12C	0.5286	0.3307	−0.0239	0.056*
C10	0.44120 (19)	0.40443 (6)	0.32157 (13)	0.0259 (3)
C30	0.02602 (19)	0.36655 (6)	0.17430 (14)	0.0280 (3)
C29	−0.0388 (2)	0.27357 (7)	0.22638 (16)	0.0363 (4)
H29	−0.0368	0.2362	0.2102	0.044*
C5	0.6005 (2)	0.17765 (7)	0.23708 (15)	0.0341 (4)
H5	0.6561	0.2113	0.2387	0.041*
C31	−0.04164 (19)	0.38390 (6)	0.27655 (14)	0.0285 (4)
C3	0.6080 (2)	0.08115 (7)	0.25618 (14)	0.0329 (4)
H3	0.6687	0.0491	0.2710	0.039*
C7	0.1638 (2)	0.12272 (6)	0.18022 (17)	0.0351 (4)
H7A	0.1443	0.0935	0.1272	0.053*
H7B	0.1274	0.1568	0.1471	0.053*
H7C	0.1003	0.1159	0.2473	0.053*
C19	0.1535 (2)	0.38600 (9)	−0.00238 (16)	0.0414 (4)
H19	0.1964	0.4110	−0.0540	0.050*
C16	0.0280 (2)	0.31077 (7)	0.14742 (15)	0.0315 (4)
C1	0.3461 (2)	0.12573 (6)	0.20924 (13)	0.0258 (3)
C23	−0.0437 (2)	0.43965 (7)	0.30300 (15)	0.0328 (4)
C22	0.0238 (2)	0.47678 (7)	0.22505 (17)	0.0391 (4)
H22	0.0231	0.5140	0.2419	0.047*
C14	0.3880 (2)	0.43610 (7)	0.42038 (15)	0.0365 (4)
H14A	0.4189	0.4739	0.4107	0.055*
H14B	0.4437	0.4219	0.4870	0.055*
H14C	0.2667	0.4332	0.4280	0.055*
C4	0.6884 (2)	0.13074 (7)	0.25835 (16)	0.0373 (4)
H4	0.8048	0.1324	0.2746	0.045*
C27	−0.1077 (2)	0.34591 (7)	0.35191 (14)	0.0321 (4)
C20	0.0917 (2)	0.40455 (7)	0.09840 (15)	0.0333 (4)
C15	0.3518 (3)	0.31677 (7)	0.40901 (16)	0.0396 (4)
H15A	0.3490	0.2787	0.3889	0.059*
H15B	0.2381	0.3292	0.4234	0.059*
H15C	0.4217	0.3216	0.4757	0.059*
C13	0.6300 (3)	0.43648 (7)	0.05471 (16)	0.0386 (4)
H13A	0.6418	0.4741	0.0772	0.058*
H13B	0.5563	0.4342	−0.0108	0.058*
H13C	0.7399	0.4218	0.0371	0.058*
C17	0.0923 (2)	0.29461 (8)	0.04643 (16)	0.0388 (4)
H17	0.0945	0.2575	0.0282	0.047*
C28	−0.1038 (2)	0.29002 (7)	0.32232 (16)	0.0375 (4)
H28	−0.1482	0.2642	0.3716	0.045*
C25	−0.1723 (2)	0.41848 (9)	0.47748 (16)	0.0437 (5)
H25	−0.2156	0.4302	0.5460	0.052*
C26	−0.1721 (2)	0.36431 (9)	0.45213 (16)	0.0408 (4)
H26	−0.2161	0.3393	0.5032	0.049*
C24	−0.1101 (2)	0.45567 (8)	0.40406 (16)	0.0407 (4)
H24	−0.1124	0.4927	0.4225	0.049*
C18	0.1533 (2)	0.33199 (9)	−0.02788 (16)	0.0434 (5)
H18	0.1951	0.3203	−0.0968	0.052*
C21	0.0882 (2)	0.46045 (7)	0.12854 (17)	0.0399 (4)
H21	0.1323	0.4864	0.0793	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0420 (7)	0.0186 (6)	0.0646 (9)	0.0012 (5)	−0.0046 (6)	0.0041 (6)
N1	0.0336 (7)	0.0203 (6)	0.0286 (7)	−0.0022 (5)	−0.0034 (6)	−0.0004 (5)
O2	0.0414 (7)	0.0184 (5)	0.0520 (8)	−0.0009 (5)	−0.0050 (6)	−0.0003 (5)
N3	0.0322 (7)	0.0201 (6)	0.0281 (7)	−0.0020 (5)	−0.0038 (5)	−0.0003 (5)
C8	0.0283 (7)	0.0235 (8)	0.0260 (8)	−0.0001 (6)	−0.0036 (6)	−0.0010 (6)
C11	0.0298 (8)	0.0231 (7)	0.0260 (8)	−0.0018 (6)	−0.0030 (6)	0.0024 (6)
C9	0.0302 (7)	0.0241 (8)	0.0253 (8)	−0.0022 (6)	−0.0035 (6)	0.0009 (6)
C6	0.0390 (9)	0.0204 (7)	0.0236 (7)	−0.0002 (6)	0.0034 (6)	−0.0002 (6)
C2	0.0402 (9)	0.0212 (7)	0.0247 (8)	0.0019 (6)	0.0041 (6)	0.0004 (6)
C12	0.0455 (10)	0.0347 (9)	0.0318 (9)	−0.0001 (7)	0.0013 (8)	−0.0085 (7)
C10	0.0293 (7)	0.0230 (7)	0.0253 (7)	−0.0003 (6)	−0.0039 (6)	−0.0020 (6)
C30	0.0253 (7)	0.0290 (8)	0.0295 (8)	0.0026 (6)	−0.0035 (6)	−0.0007 (6)
C29	0.0346 (9)	0.0260 (8)	0.0480 (11)	0.0007 (7)	−0.0064 (8)	0.0006 (7)
C5	0.0358 (9)	0.0313 (9)	0.0352 (9)	−0.0066 (7)	0.0046 (7)	−0.0028 (7)
C31	0.0249 (7)	0.0295 (8)	0.0309 (8)	0.0027 (6)	−0.0051 (6)	−0.0019 (6)
C3	0.0356 (9)	0.0315 (8)	0.0316 (8)	0.0080 (7)	0.0023 (7)	0.0009 (7)
C7	0.0347 (9)	0.0236 (8)	0.0468 (10)	−0.0010 (6)	−0.0048 (8)	0.0001 (7)
C19	0.0368 (9)	0.0528 (11)	0.0346 (9)	0.0026 (8)	0.0026 (8)	0.0066 (8)
C16	0.0277 (8)	0.0294 (8)	0.0372 (9)	0.0043 (6)	−0.0058 (7)	−0.0039 (7)
C1	0.0311 (8)	0.0205 (7)	0.0257 (7)	−0.0006 (6)	0.0014 (6)	−0.0006 (6)
C23	0.0299 (8)	0.0311 (8)	0.0371 (9)	0.0044 (6)	−0.0080 (7)	−0.0064 (7)
C22	0.0365 (9)	0.0262 (8)	0.0543 (12)	0.0015 (7)	−0.0066 (8)	−0.0027 (8)
C14	0.0450 (10)	0.0320 (9)	0.0325 (9)	0.0007 (7)	0.0027 (8)	−0.0079 (7)
C4	0.0325 (9)	0.0423 (10)	0.0373 (9)	0.0011 (7)	0.0024 (7)	−0.0029 (8)
C27	0.0270 (8)	0.0383 (9)	0.0307 (8)	0.0022 (7)	−0.0047 (6)	0.0020 (7)
C20	0.0292 (8)	0.0364 (9)	0.0340 (9)	0.0011 (7)	−0.0022 (7)	0.0041 (7)
C15	0.0521 (11)	0.0327 (9)	0.0342 (9)	−0.0085 (8)	0.0042 (8)	0.0054 (7)
C13	0.0511 (11)	0.0326 (9)	0.0323 (9)	−0.0054 (8)	0.0034 (8)	0.0056 (7)
C17	0.0368 (9)	0.0383 (10)	0.0411 (10)	0.0091 (7)	−0.0051 (8)	−0.0100 (8)
C28	0.0357 (9)	0.0337 (9)	0.0429 (10)	−0.0029 (7)	−0.0040 (8)	0.0086 (8)
C25	0.0390 (10)	0.0618 (13)	0.0301 (9)	0.0119 (9)	−0.0042 (8)	−0.0112 (9)
C26	0.0348 (9)	0.0567 (12)	0.0306 (9)	0.0041 (8)	−0.0014 (7)	0.0048 (8)
C24	0.0399 (9)	0.0420 (10)	0.0398 (10)	0.0090 (8)	−0.0095 (8)	−0.0124 (8)
C18	0.0405 (10)	0.0575 (12)	0.0322 (9)	0.0105 (9)	0.0013 (8)	−0.0066 (8)
C21	0.0371 (9)	0.0324 (9)	0.0499 (11)	−0.0034 (7)	−0.0038 (8)	0.0072 (8)

Geometric parameters (Å, º)

O1—C2	1.362 (2)	C7—H7A	0.9800
O1—H1	0.8400	C7—H7B	0.9800
N1—C8	1.341 (2)	C7—H7C	0.9800
N1—C11	1.343 (2)	C19—C18	1.380 (3)
O2—C6	1.3623 (19)	C19—C20	1.402 (3)
O2—H2	0.8400	C19—H19	0.9500
N3—C9	1.341 (2)	C16—C17	1.393 (3)
N3—C10	1.343 (2)	C23—C24	1.400 (3)
C8—C9	1.400 (2)	C23—C22	1.433 (3)
C8—C12	1.501 (2)	C22—C21	1.347 (3)
C11—C10	1.397 (2)	C22—H22	0.9500
C11—C15	1.502 (2)	C14—H14A	0.9800
C9—C13	1.503 (2)	C14—H14B	0.9800
C6—C5	1.387 (2)	C14—H14C	0.9800
C6—C1	1.400 (2)	C4—H4	0.9500
C2—C3	1.381 (2)	C27—C26	1.403 (3)
C2—C1	1.400 (2)	C27—C28	1.437 (3)
C12—H12A	0.9800	C20—C21	1.439 (3)
C12—H12B	0.9800	C15—H15A	0.9800
C12—H12C	0.9800	C15—H15B	0.9800
C10—C14	1.500 (2)	C15—H15C	0.9800
C30—C20	1.425 (2)	C13—H13A	0.9800
C30—C31	1.426 (2)	C13—H13B	0.9800
C30—C16	1.427 (2)	C13—H13C	0.9800
C29—C28	1.344 (3)	C17—C18	1.389 (3)
C29—C16	1.440 (3)	C17—H17	0.9500
C29—H29	0.9500	C28—H28	0.9500
C5—C4	1.385 (3)	C25—C24	1.382 (3)
C5—H5	0.9500	C25—C26	1.383 (3)
C31—C27	1.422 (2)	C25—H25	0.9500
C31—C23	1.425 (2)	C26—H26	0.9500
C3—C4	1.393 (3)	C24—H24	0.9500
C3—H3	0.9500	C18—H18	0.9500
C7—C1	1.497 (2)	C21—H21	0.9500
C2—O1—H1	109.5	C2—C1—C7	121.04 (14)
C8—N1—C11	119.02 (13)	C6—C1—C7	121.29 (14)
C6—O2—H2	109.5	C24—C23—C31	118.67 (17)
C9—N3—C10	118.94 (13)	C24—C23—C22	122.96 (17)
N1—C8—C9	120.35 (14)	C31—C23—C22	118.37 (16)
N1—C8—C12	117.73 (14)	C21—C22—C23	121.98 (17)
C9—C8—C12	121.92 (15)	C21—C22—H22	119.0
N1—C11—C10	120.58 (14)	C23—C22—H22	119.0
N1—C11—C15	117.58 (14)	C10—C14—H14A	109.5
C10—C11—C15	121.84 (15)	C10—C14—H14B	109.5
N3—C9—C8	120.65 (14)	H14A—C14—H14B	109.5
N3—C9—C13	117.62 (14)	C10—C14—H14C	109.5
C8—C9—C13	121.73 (15)	H14A—C14—H14C	109.5
O2—C6—C5	122.63 (15)	H14B—C14—H14C	109.5
O2—C6—C1	116.06 (15)	C5—C4—C3	120.75 (17)
C5—C6—C1	121.31 (15)	C5—C4—H4	119.6
O1—C2—C3	123.03 (15)	C3—C4—H4	119.6
O1—C2—C1	115.19 (15)	C26—C27—C31	118.88 (17)
C3—C2—C1	121.78 (15)	C26—C27—C28	122.77 (17)
C8—C12—H12A	109.5	C31—C27—C28	118.34 (16)
C8—C12—H12B	109.5	C19—C20—C30	118.76 (17)
H12A—C12—H12B	109.5	C19—C20—C21	123.19 (17)
C8—C12—H12C	109.5	C30—C20—C21	118.04 (16)
H12A—C12—H12C	109.5	C11—C15—H15A	109.5
H12B—C12—H12C	109.5	C11—C15—H15B	109.5
N3—C10—C11	120.45 (14)	H15A—C15—H15B	109.5
N3—C10—C14	117.37 (14)	C11—C15—H15C	109.5
C11—C10—C14	122.18 (14)	H15A—C15—H15C	109.5
C20—C30—C31	120.49 (15)	H15B—C15—H15C	109.5
C20—C30—C16	119.60 (16)	C9—C13—H13A	109.5
C31—C30—C16	119.90 (15)	C9—C13—H13B	109.5
C28—C29—C16	122.02 (16)	H13A—C13—H13B	109.5
C28—C29—H29	119.0	C9—C13—H13C	109.5
C16—C29—H29	119.0	H13A—C13—H13C	109.5
C4—C5—C6	119.41 (16)	H13B—C13—H13C	109.5
C4—C5—H5	120.3	C18—C17—C16	120.88 (18)
C6—C5—H5	120.3	C18—C17—H17	119.6
C27—C31—C23	119.91 (16)	C16—C17—H17	119.6
C27—C31—C30	120.36 (15)	C29—C28—C27	121.36 (17)
C23—C31—C30	119.73 (16)	C29—C28—H28	119.3
C2—C3—C4	119.08 (16)	C27—C28—H28	119.3
C2—C3—H3	120.5	C24—C25—C26	120.62 (18)
C4—C3—H3	120.5	C24—C25—H25	119.7
C1—C7—H7A	109.5	C26—C25—H25	119.7
C1—C7—H7B	109.5	C25—C26—C27	120.79 (19)
H7A—C7—H7B	109.5	C25—C26—H26	119.6
C1—C7—H7C	109.5	C27—C26—H26	119.6
H7A—C7—H7C	109.5	C25—C24—C23	121.12 (18)
H7B—C7—H7C	109.5	C25—C24—H24	119.4
C18—C19—C20	121.07 (18)	C23—C24—H24	119.4
C18—C19—H19	119.5	C19—C18—C17	120.54 (18)
C20—C19—H19	119.5	C19—C18—H18	119.7
C17—C16—C30	119.12 (17)	C17—C18—H18	119.7
C17—C16—C29	122.87 (16)	C22—C21—C20	121.38 (17)
C30—C16—C29	118.01 (16)	C22—C21—H21	119.3
C2—C1—C6	117.66 (15)	C20—C21—H21	119.3

(MRE_TMP_TOL)

Crystal data

C44H50N4O4	V = 985.0 (16) Å^3
Mr = 698.88	Z = 1
Triclinic, P1	F(000) = 374
a = 7.195 (7) Å	Dx = 1.178 Mg m^−3
b = 8.865 (8) Å	Mo Kα radiation, λ = 0.71073 Å
c = 15.981 (15) Å	µ = 0.08 mm^−1
α = 80.52 (3)°	T = 150 K
β = 84.20 (3)°	Plate, colorless
γ = 79.19 (2)°	0.31 × 0.22 × 0.15 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3427 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.133
profile data from ω–scans	θmax = 27.0°, θmin = 1.3°
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	h = −9→9
Tmin = 0.521, Tmax = 1.000	k = −11→11
10032 measured reflections	l = −20→20
4292 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) = 0.197	w = 1/[σ^2(Fo^2) + (0.0934P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.002
4292 reflections	Δρmax = 0.28 e Å^−3
242 parameters	Δρmin = −0.33 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.10889 (16)	0.20037 (12)	0.06943 (7)	0.0345 (3)
H1	0.1909	0.2583	0.0584	0.052*
N1	0.36756 (18)	0.40307 (13)	0.01879 (8)	0.0274 (3)
O2	−0.07905 (16)	−0.19790 (13)	0.27487 (7)	0.0399 (3)
H2	−0.0519	−0.2501	0.3222	0.060*
C2	0.1440 (2)	0.10273 (15)	0.14441 (9)	0.0249 (3)
N2	−0.00966 (19)	−0.39468 (15)	0.42655 (8)	0.0334 (3)
C6	0.0492 (2)	−0.10139 (16)	0.24859 (9)	0.0273 (3)
C1	0.01843 (19)	−0.00060 (15)	0.17205 (9)	0.0239 (3)
C10	0.5292 (2)	0.36022 (16)	−0.02784 (9)	0.0262 (3)
C7	−0.1463 (2)	−0.00336 (18)	0.12152 (10)	0.0314 (4)
H7A	−0.2110	0.1032	0.1042	0.047*
H7B	−0.2353	−0.0629	0.1566	0.047*
H7C	−0.0997	−0.0521	0.0709	0.047*
C3	0.2985 (2)	0.10547 (18)	0.18986 (10)	0.0310 (4)
H3	0.3831	0.1761	0.1699	0.037*
C5	0.2037 (2)	−0.10073 (18)	0.29508 (10)	0.0339 (4)
H5	0.2240	−0.1703	0.3466	0.041*
C9	0.3358 (2)	0.54136 (16)	0.04664 (9)	0.0267 (3)
C13	0.0619 (2)	−0.54504 (18)	0.42336 (10)	0.0320 (4)
C14	−0.0715 (2)	−0.34825 (18)	0.50166 (10)	0.0332 (4)
C11	0.5572 (3)	0.20503 (17)	−0.05809 (10)	0.0354 (4)
H11A	0.4457	0.1561	−0.0393	0.053*
H11B	0.6700	0.1383	−0.0344	0.053*
H11C	0.5741	0.2195	−0.1203	0.053*
C21	−0.4020 (2)	−0.5610 (2)	0.38430 (12)	0.0384 (4)
C12	0.1287 (3)	−0.5909 (2)	0.33811 (11)	0.0425 (4)
H12A	0.1046	−0.4998	0.2941	0.064*
H12B	0.0603	−0.6707	0.3274	0.064*
H12C	0.2650	−0.6321	0.3368	0.064*
C16	−0.3537 (2)	−0.7187 (2)	0.37448 (13)	0.0429 (4)
H16	−0.3627	−0.7971	0.4223	0.051*
C22	−0.4699 (2)	−0.5185 (2)	0.46632 (13)	0.0428 (4)
C20	−0.3836 (2)	−0.4480 (2)	0.31347 (13)	0.0435 (4)
H20	−0.4136	−0.3412	0.3196	0.052*
C4	0.3262 (2)	0.00188 (19)	0.26551 (11)	0.0365 (4)
H4	0.4312	0.0022	0.2970	0.044*
C17	−0.2928 (3)	−0.7596 (2)	0.29475 (14)	0.0481 (5)
H17	−0.2617	−0.8662	0.2882	0.058*
C8	0.1525 (3)	0.5853 (2)	0.09708 (11)	0.0418 (4)
H8A	0.0697	0.6675	0.0626	0.063*
H8B	0.1774	0.6228	0.1485	0.063*
H8C	0.0903	0.4943	0.1131	0.063*
C19	−0.3218 (3)	−0.4908 (2)	0.23417 (14)	0.0486 (5)
H19	−0.3101	−0.4132	0.1862	0.058*
C18	−0.2770 (3)	−0.6469 (2)	0.22468 (13)	0.0483 (5)
H18	−0.2358	−0.6759	0.1703	0.058*
C15	−0.1509 (3)	−0.1787 (2)	0.50096 (14)	0.0531 (5)
H15A	−0.1255	−0.1216	0.4443	0.080*
H15B	−0.0909	−0.1386	0.5430	0.080*
H15C	−0.2881	−0.1655	0.5151	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0384 (7)	0.0364 (6)	0.0311 (6)	−0.0175 (5)	−0.0065 (5)	0.0034 (5)
N1	0.0316 (7)	0.0253 (6)	0.0256 (6)	−0.0075 (5)	−0.0036 (5)	−0.0009 (5)
O2	0.0378 (7)	0.0447 (7)	0.0385 (7)	−0.0222 (5)	−0.0124 (5)	0.0133 (5)
C2	0.0262 (7)	0.0247 (6)	0.0250 (7)	−0.0060 (6)	−0.0013 (5)	−0.0056 (5)
N2	0.0311 (7)	0.0375 (7)	0.0336 (7)	−0.0148 (6)	−0.0107 (6)	0.0041 (6)
C6	0.0234 (7)	0.0286 (7)	0.0305 (7)	−0.0078 (6)	−0.0025 (6)	−0.0025 (6)
C1	0.0219 (7)	0.0250 (6)	0.0265 (7)	−0.0055 (5)	−0.0022 (5)	−0.0067 (5)
C10	0.0332 (8)	0.0242 (6)	0.0215 (6)	−0.0056 (6)	−0.0058 (5)	−0.0013 (5)
C7	0.0303 (8)	0.0377 (8)	0.0294 (8)	−0.0128 (6)	−0.0080 (6)	−0.0027 (6)
C3	0.0272 (8)	0.0323 (7)	0.0369 (8)	−0.0133 (6)	−0.0028 (6)	−0.0052 (6)
C5	0.0305 (8)	0.0370 (8)	0.0331 (8)	−0.0078 (6)	−0.0107 (6)	0.0048 (6)
C9	0.0309 (8)	0.0273 (7)	0.0219 (7)	−0.0063 (6)	−0.0028 (5)	−0.0023 (5)
C13	0.0274 (8)	0.0386 (8)	0.0335 (8)	−0.0153 (6)	−0.0090 (6)	−0.0005 (6)
C14	0.0301 (8)	0.0356 (8)	0.0372 (8)	−0.0159 (6)	−0.0105 (6)	0.0012 (7)
C11	0.0451 (10)	0.0263 (7)	0.0367 (8)	−0.0048 (7)	−0.0071 (7)	−0.0091 (6)
C21	0.0184 (8)	0.0479 (9)	0.0549 (11)	−0.0082 (7)	−0.0041 (7)	−0.0214 (8)
C12	0.0389 (10)	0.0548 (10)	0.0363 (9)	−0.0127 (8)	−0.0092 (7)	−0.0050 (7)
C16	0.0275 (9)	0.0440 (9)	0.0607 (11)	−0.0099 (7)	0.0022 (8)	−0.0170 (8)
C22	0.0249 (9)	0.0505 (10)	0.0596 (11)	−0.0105 (7)	−0.0031 (8)	−0.0229 (8)
C20	0.0290 (9)	0.0413 (9)	0.0639 (12)	−0.0012 (7)	−0.0128 (8)	−0.0182 (8)
C4	0.0290 (8)	0.0418 (9)	0.0421 (9)	−0.0104 (7)	−0.0132 (7)	−0.0044 (7)
C17	0.0321 (9)	0.0468 (10)	0.0716 (14)	−0.0102 (8)	0.0033 (8)	−0.0271 (9)
C8	0.0386 (10)	0.0415 (9)	0.0443 (10)	−0.0080 (7)	0.0099 (8)	−0.0096 (7)
C19	0.0356 (10)	0.0566 (11)	0.0538 (11)	−0.0013 (8)	−0.0150 (8)	−0.0097 (9)
C18	0.0328 (10)	0.0649 (12)	0.0540 (11)	−0.0077 (9)	−0.0066 (8)	−0.0272 (9)
C15	0.0650 (14)	0.0384 (9)	0.0537 (12)	−0.0079 (9)	−0.0059 (10)	−0.0004 (8)

Geometric parameters (Å, º)

O1—C2	1.3734 (19)	C14—C15	1.503 (3)
O1—H1	0.8400	C11—H11A	0.9800
N1—C10	1.343 (2)	C11—H11B	0.9800
N1—C9	1.344 (2)	C11—H11C	0.9800
O2—C6	1.363 (2)	C21—C20	1.396 (3)
O2—H2	0.8400	C21—C16	1.407 (3)
C2—C1	1.395 (2)	C21—C22	1.436 (3)
C2—C3	1.394 (2)	C12—H12A	0.9800
N2—C14	1.339 (2)	C12—H12B	0.9800
N2—C13	1.343 (2)	C12—H12C	0.9800
C6—C5	1.399 (2)	C16—C17	1.388 (3)
C6—C1	1.401 (2)	C16—H16	0.9500
C1—C7	1.506 (2)	C22—C22^iii	1.193 (4)
C10—C9^i	1.403 (2)	C20—C19	1.389 (3)
C10—C11	1.504 (2)	C20—H20	0.9500
C7—H7A	0.9800	C4—H4	0.9500
C7—H7B	0.9800	C17—C18	1.384 (3)
C7—H7C	0.9800	C17—H17	0.9500
C3—C4	1.400 (2)	C8—H8A	0.9800
C3—H3	0.9500	C8—H8B	0.9800
C5—C4	1.380 (2)	C8—H8C	0.9800
C5—H5	0.9500	C19—C18	1.390 (3)
C9—C10^i	1.403 (2)	C19—H19	0.9500
C9—C8	1.496 (2)	C18—H18	0.9500
C13—C14^ii	1.398 (2)	C15—H15A	0.9800
C13—C12	1.493 (3)	C15—H15B	0.9800
C14—C13^ii	1.398 (2)	C15—H15C	0.9800
C2—O1—H1	109.5	H11B—C11—H11C	109.5
C10—N1—C9	119.46 (13)	C20—C21—C16	119.05 (18)
C6—O2—H2	109.5	C20—C21—C22	121.01 (17)
O1—C2—C1	116.52 (13)	C16—C21—C22	119.94 (18)
O1—C2—C3	121.66 (13)	C13—C12—H12A	109.5
C1—C2—C3	121.82 (13)	C13—C12—H12B	109.5
C14—N2—C13	119.65 (13)	H12A—C12—H12B	109.5
O2—C6—C5	122.47 (13)	C13—C12—H12C	109.5
O2—C6—C1	116.57 (14)	H12A—C12—H12C	109.5
C5—C6—C1	120.97 (14)	H12B—C12—H12C	109.5
C2—C1—C6	118.10 (14)	C17—C16—C21	119.85 (18)
C2—C1—C7	121.09 (13)	C17—C16—H16	120.1
C6—C1—C7	120.81 (13)	C21—C16—H16	120.1
N1—C10—C9^i	120.16 (14)	C22^iii—C22—C21	178.5 (3)
N1—C10—C11	117.40 (14)	C19—C20—C21	120.42 (18)
C9^i—C10—C11	122.44 (15)	C19—C20—H20	119.8
C1—C7—H7A	109.5	C21—C20—H20	119.8
C1—C7—H7B	109.5	C5—C4—C3	121.11 (15)
H7A—C7—H7B	109.5	C5—C4—H4	119.4
C1—C7—H7C	109.5	C3—C4—H4	119.4
H7A—C7—H7C	109.5	C18—C17—C16	120.72 (18)
H7B—C7—H7C	109.5	C18—C17—H17	119.6
C2—C3—C4	118.54 (14)	C16—C17—H17	119.6
C2—C3—H3	120.7	C9—C8—H8A	109.5
C4—C3—H3	120.7	C9—C8—H8B	109.5
C4—C5—C6	119.44 (14)	H8A—C8—H8B	109.5
C4—C5—H5	120.3	C9—C8—H8C	109.5
C6—C5—H5	120.3	H8A—C8—H8C	109.5
N1—C9—C10^i	120.38 (14)	H8B—C8—H8C	109.5
N1—C9—C8	117.58 (14)	C20—C19—C18	120.22 (19)
C10^i—C9—C8	122.03 (15)	C20—C19—H19	119.9
N2—C13—C14^ii	119.82 (16)	C18—C19—H19	119.9
N2—C13—C12	117.56 (14)	C17—C18—C19	119.73 (19)
C14^ii—C13—C12	122.62 (17)	C17—C18—H18	120.1
N2—C14—C13^ii	120.53 (16)	C19—C18—H18	120.1
N2—C14—C15	117.11 (14)	C14—C15—H15A	109.5
C13^ii—C14—C15	122.36 (17)	C14—C15—H15B	109.5
C10—C11—H11A	109.5	H15A—C15—H15B	109.5
C10—C11—H11B	109.5	C14—C15—H15C	109.5
H11A—C11—H11B	109.5	H15A—C15—H15C	109.5
C10—C11—H11C	109.5	H15B—C15—H15C	109.5
H11A—C11—H11C	109.5
O1—C2—C1—C6	−179.63 (12)	C10—N1—C9—C8	178.99 (13)
C3—C2—C1—C6	1.2 (2)	C14—N2—C13—C14^ii	−0.1 (2)
O1—C2—C1—C7	0.0 (2)	C14—N2—C13—C12	179.96 (13)
C3—C2—C1—C7	−179.17 (14)	C13—N2—C14—C13^ii	0.1 (2)
O2—C6—C1—C2	178.29 (13)	C13—N2—C14—C15	−179.68 (15)
C5—C6—C1—C2	−1.3 (2)	C20—C21—C16—C17	−1.4 (2)
O2—C6—C1—C7	−1.3 (2)	C22—C21—C16—C17	178.33 (16)
C5—C6—C1—C7	179.06 (14)	C16—C21—C20—C19	1.2 (2)
C9—N1—C10—C9^i	0.5 (2)	C22—C21—C20—C19	−178.56 (15)
C9—N1—C10—C11	−179.49 (12)	C6—C5—C4—C3	0.1 (3)
O1—C2—C3—C4	−179.57 (14)	C2—C3—C4—C5	−0.2 (3)
C1—C2—C3—C4	−0.5 (2)	C21—C16—C17—C18	0.7 (3)
O2—C6—C5—C4	−178.89 (15)	C21—C20—C19—C18	−0.2 (3)
C1—C6—C5—C4	0.7 (3)	C16—C17—C18—C19	0.3 (3)
C10—N1—C9—C10^i	−0.5 (2)	C20—C19—C18—C17	−0.5 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.96	2.796 (2)	173
O2—H2···N2	0.84	1.94	2.774 (3)	171
C8—H8A···O1^iv	0.98	2.58	3.498 (3)	156

Symmetry code: (iv) −x, −y+1, −z.