Combinatorial selection of molecular conformations and supramolecular synthons in quercetin cocrystal landscapes: a route to ternary solids

The crystallization of 28 binary and ternary cocrystals of quercetin with dibasic coformers is analyzed in terms of a combinatorial selection from a solution of preferred molecular conformations and supramolecular synthons. The crystal structures are characterized by distinctive O—H⋯N and O—H⋯O based synthons and are classified as nonporous, porous and helical. Variability in molecular conformation and synthon structure led to an increase in the energetic and structural space around the crystallization event. This space is the crystal structure landscape of the compound and is explored by fine-tuning the experimental conditions of crystallization. In the landscape context, we develop a strategy for the isolation of ternary cocrystals with the use of auxiliary template molecules to reduce the molecular and supramolecular `confusion' that is inherent in a molecule like quercetin. The absence of concomitant polymorphism in this study highlights the selectivity in conformation and synthon choice from the virtual combinatorial library in solution.

1. Introduction

Polymorphism (Groth, 1906–1919; Deffet, 1942) is intrinsic to organic compounds and multiple crystalline phases exist because of contrasting kinetic and thermodynamic preferences during crystallization (Desiraju, 2002, 2007, 2013). The phenomenon may be more common for molecules which have both conformational flexibility and hydrogen-bonding propensity, although it is by no means unknown to other categories of substances (Sarma & Desiraju, 1999; Desiraju, 1997b). Conformationally flexible molecules provide alternative packing arrangements because rotations around single bonds afford differently shaped molecules (Nangia, 2008; Amadei et al., 1998; Bhatt & Desiraju, 2007; Bond et al., 2007a,b). Again, the presence of multiple hydrogen bond functionalities facilitates the emergence of several crystalline forms because of the different supramolecular synthon possibilities that could ensue (Jetti et al., 2003; Roy & Matzger, 2009; Chen et al., 2005; López-Mejías et al., 2012). The (molecular) energy differences between conformations is comparable to the (crystal) energy differences between polymorphs (<20 kJ mol⁻¹), and therefore a combination of both factors enhances the likelihood of polymorphism in organic compounds, especially if small changes in experimental conditions result (Nangia, 2008). This energy profile may contain various dynamically equilibrated molecular conformations and supramolecular synthons in solution that, in combination, would be capable of providing a large number of crystalline phases from the supersaturated crystallizing medium. These phases, which would be virtual save for some extenuating circumstance, may be amplified by solvent control or by using suitable template molecules to give isolable solids (Blagden & Davey, 2003; Kulkarni et al., 2012; Staab et al., 1990; Friščič & MacGillivray, 2009). If we consider the crystal as a supramolecular entity (Desiraju, 1996), both factors, molecular conformation and multiplicity of synthons, collectively increase the energetic and structural space around the reaction trajectories in this supramolecular synthesis. This space is the crystal structure landscape of the compound (Thakur et al., 2015; Dubey et al., 2012, Dubey & Desiraju, 2014a,b).

The concept of polymorphism is very well studied in single component systems but systematic exploration of cocrystal polymorphism has only recently begun in the crystal engineering context (Aitipamula et al., 2014). We have performed a detailed landscape exploration based on the conformationally flexible orcinol (5-methylresorcinol) molecule and its cocrystals with N-bases (Mukherjee et al., 2011). We found that all possible conformations of the orcinol molecule can exist in these crystalline forms: syn–syn (four cocrystals), anti–anti (seven cocrystals), syn–anti (five cocrystals). We further showed that the orcinol:4,4′-bipyridine (ORC:44BP) cocrystal landscape consists of five anhydrous crystal forms, but that all forms have just one of the orcinol conformations (anti–anti), however, with different packing arrangements (Dubey et al., 2014). Cocrystal polymorphism can also involve changes in the main synthons themselves (Desiraju, 1995), the so-called synthon polymorphism (Sreekanth et al., 2007; Mukherjee & Desiraju, 2011). The 4-hydroxybenzoic acid:4,4′-bipyridine cocrystal, for example, shows efficient synthon selection with different experimental conditions leading to fundamentally different crystal forms (Mukherjee & Desiraju, 2011). Synthon polymorphism in cocrystals may be considered to be combinatorial selection from a virtual synthon library. This idea of selection has been elaborated in solution chemistry previously (Lehn, 1999, 2007). Recently, we interpreted the extensive polymorphic modifications in phloroglucinol:1,2-bis(4-pyridyl)ethylene (PGL:DPE) and phloroglucinol:phenazine (PGL:PHE) cocrystal systems on this basis and showed selective amplification of synthons using auxiliary template molecules (Dubey & Desiraju, 2014a).

Quercetin (QUE) is an important polyphenol flavonoid which shows a variety of biological properties including antioxidant behavior (Grassi et al., 2010; Zhang et al., 2011). Using the cocrystal landscapes of quercetin (Kavuru et al., 2010) with dibasic coformers, i.e. tetramethylpyrazine (TMP), 4,4′-bipyridine (44BP), 1,2-bis(4-pyridyl)ethylene (DPE-1), 1,2-bis(4-pyridyl)ethane (DPE-2), 4,4′-azopyridine (44AP), phenazine (PHE), we extend here the idea of a combinatorial library towards prenucleation events where a conformationally flexible compound has a large number of virtual conformations. This approach allows one to consider the aggregation of these flexible molecules towards heteroclusters as synthon selection from a virtual library leading eventually to nucleation events and the final crystal structure (Desiraju, 1997a; Davey et al., 2013).

2. Experimental

All datasets were collected on a Rigaku Mercury 375R/MCCD (XtaLABmini) diffractometer with a graphite monochromator using Mo Kα radiation, attached with a Rigaku low-temperature gas spray cooler. The data were processed with CrystalClear software (Rigaku, 2009). QUE:DPE-II (form III) was collected on an Oxford Xcalibur diffractometer with a microfocus X-ray source (Mo Kα) equipped with a Cryojet-HT nitrogen gas stream cooling device and data were processed with CrysAlisPro (Oxford, 2009). Data for some of the crystals, the QUE:DPE-I (form IV), QUE:DPE-II (form II), QUE:44AP (form II), QUE:PHE (forms III and IV) and QUE:DPE-I:ANT were collected on a Bruker Kappa Apex II CCD diffractometer using Mo Kα radiation and an Oxford cryosystems N₂ open-flow cryostat (Bruker, 2006). Cell refinement, data integration and data reduction were carried out using the SAINT-Plus program. Crystal structures were solved by direct methods and refined in the spherical-atom approximation using SHELXL2012 (Sheldrick, 2008) from the WinGX suite (Farrugia, 1999). All non-H atoms were refined anisotropically. The H atoms were fixed on a riding model and acidic H atoms were located via Fourier maps. Precise experimental details of each crystal structure are provided in the supporting information .

3. Results and discussion

This section is divided into a description of the landscapes and the combinatorial analysis of the crystallization events. The primary driving force in the formation of a cocrystal is enthalpically driven synthon formation in solution that involves two or more chemically distinct molecules. A particular synthon is also associated with certain conformations of the QUE molecule. Which conformation and which synthon is preferred in any instance depend on the structure of the coformer, the presence of auxiliary molecules and other experimental variables.

3.1. Quercetin cocrystal landscapes

Quercetin has five hydroxy groups (Fig. 1) and the mutual orientations of these groups provide a variety of putative conformations that constitute a virtual conformational library (supporting information ). This scenario is further complicated by the conformational possibilities brought about with the flexible C-ring. We performed extensive cocrystallization experiments with dibasic coformers (supporting information ). These crystal structures are characterized by several O—H⋯N and/or O—H⋯O based supramolecular synthons which are all rather distinctive and lead to structure types that we refer to in this paper as nonporous, porous and helical within the extended domain of the quercetin cocrystal landscapes. There are other synthon possibilities which were revealed in later cocrystal screening experiments, giving a hint about the virtual nature of this library. Figs. 2 and 3 illustrate quercetin conformations and a schematic representation of the supramolecular synthons discussed here. In general, the second (OH2) and third (OH3) hydroxy groups of quercetin are conformationally locked by intramolecular hydrogen bonding, while OH1, OH4 and OH5 are responsible for the supramolecular development of various intricate hydrogen bonding patterns in the crystal structures. The supporting information gives a list of 12 conformations and their energies. It is interesting that the most stable conformation (Conf 2B) does not feature in the experimental crystal structures. This could be because of a trade-off between intra- and intermolecular factors.

Figure 1 Flipping of the (5) OH group by rotation of the flexible C—C single bond in quercetin.

Figure 2 Molecular conformations in quercetin cocrystal landscapes.

Figure 3 Supramolecular synthons in quercetin cocrystal landscapes. All the members of this synthon library may be interpreted based on O—H⋯O and/or O—H⋯N hydrogen bonding patterns, but each synthon is distinct from any of the others based on topological considerations.

In the quercetin–tetramethyl­pyrazine (QUE:TMP) cocrystal system, we were able to isolate four crystal forms: two anhydrates, a 1,4-dioxane solvate and a tetrahydrofuran (thf) solvate. The crystal stoichiometries can be 1:3, 1:2 or 1:1. QUE is underexpressed in the crystal in relation to the amount taken in solution for crystallization. So a 1:3 anhydrate, form I (space group Pc), is obtained from a solution that contains QUE and TMP in a 1:1 ratio, while a 1:2 anhydrate, form II (space group P2₁/c), is obtained when the QUE:TMP ratio taken in solution is 2:1. In form I, quercetin acquires the Conf 6B conformation that accelerates the selection of synthon A from the solution library. In this crystal structure, OH1, OH2, OH3 and OH4 groups are involved in O–H⋯N hydrogen bonding while OH2 and OH5 groups participate with O–H⋯O hydrogen bonds. Form II also has Conf 6B, but a different supramolecular synthon, synthon B. So we observe a preferential trend of O—H⋯O over O—H⋯N with increasing QUE content in solution, as might be expected. This trend continues when the QUE content is increased further. When QUE and TMP are taken in a 3:1 ratio in solution, the outcome are two 1:1 cocrystals, form III and form IV, both of which have Conf 5B and synthon E. In these crystal structures, the molecular conformation and synthon selection mutually provide a channel arrangement that facilitates porosity along [100]. This one-dimensional porous channel is filled with dioxane and thf solvents as a guest, respectively. In the crystal structure landscape context this movement from a close packed to a porous structure highlights that subtle factors underlie the selection of certain high-energy conformations leading to particular synthons and hydrogen bond arrangements. This combinatorial selection of molecular conformation as well as the amplification of `correct' synthons could be delicately controlled by changing the experimental conditions – stoichiometric ratios or solvents – during crystallization.

The quercetin–4,4′-bipyridine cocrystal system (QUE:44BP) has four crystal forms. Three of them are porous, with basically the same structure as the porous QUE:TMP crystals, and have 1:1 stoichiometry. As in QUE:TMP, these forms have the same conformation Conf 5B and the same synthon E. These crystal structures accommodate 1,4-dioxane, thf and even coformer (44BP) as a guest in the larger porous pocket (Fig. 4). When QUE and 44BP were taken in 1:4 ratios in solution for crystallization, a fourth form was obtained in which QUE switches its molecular conformation to the high energy Conf 7B. This crystal form is a 1:3 QUE:44BP monohydrate with masked synthon F where water is involved in complex hydrogen bond patterns. MacGillivray et al. have utilized the appropriate term masked synthon to describe a situation wherein water actively participates in the development of the supramolecular synthon (Sander et al., 2013). In the next step, we replaced the 44BP coformer with 1,2-bis(4-pyridyl)ethylene (DPE-I) and explored its corresponding structural space. The QUE:DPE-I landscape contains five crystal forms – two anhydrates and one solvate each of 1,4-dioxane, thf and DMF. The latter pseudopolymorphic structures are all porous with the solvents situated in the open pockets. Extending the argument, we have described recently that replacement of DPE-I with 1,2-bis(4-pyridyl)ethane, DPE-II, can extend the structural landscape (Dubey & Desiraju, 2015). In the present study we made cocrystals of QUE with DPE-II and also with 4,4′-azopyridine (44AP), which is chemically similar to DPE-I and DPE-II. We found the same conformation Conf 6B and porous synthon E in these structures.

Figure 4 Porous molecular arrangements in quercetin cocrystal landscapes; QUE:TMP (left), QUE:44BP (middle), QUE:DPE (right). Compounds are color coded: green – quercetin; blue – coformer.

Let us now consider the anhydrates. By altering the experimental conditions, we found that crystallization of a 1:1 ratio of QUE and DPE-I provides two forms: the first has a 1:1 QUE:DPE-I stoichiometry with Conf 1B and synthon H, while the other is a 1:2 QUE:DPE-I cocrystal with Conf 7B and synthon G. The latter illustrates a new helical structure type illustrated in Fig. 5, which shows different molecular and supramolecular features from the previously described nonporous and porous structure types and correspondingly enhances the domain of the structural space available. Similar to the pseudopolymorphs, the anhydrates also follow the same trend after coformer replacement of DPE-I by DPE-II or 44AP and hints about the robustness of conformation and synthon selection during crystallization. Changing the experimental conditions for QUE:TMP, QUE:44BP and QUE:DPE-I allows one to move within a landscape from nonporous to porous and thereafter to helical crystal structures. In most cases the corresponding DPE-I, DPE-II and 44AP cocrystal structures are isomorphous. However, in the 2:1 QUE:DPE-II cocrystal there is a different synthon C despite the same conformation Conf 6B. There are a number of structures lying within a small energy window, all with the same conformation but different synthon possibilities. We did not observe any instance of concomitant polymorphism so selectivity in synthon choice is clearly present. The crystallographic details of the crystal structures are given in the supporting information .

Figure 5 Helical molecular arrangements in quercetin cocrystal landscapes. Compounds are color coded: green – quercetin; blue – coformer.

Finally, the quercetin–phenazine cocrystal landscape (QUE:PHE) is very comparable and has five crystal forms: two anhydrates, a methanolate, a 1,4-dioxane solvate and a monohydrate. Of these crystal forms, two are porous with Conf 5B and synthon E and their one-directional porous channel is occupied by 1,4-dioxane and PHE as a guest molecule. In the methanolate, Conf 6B is taken with synthon D. PHE is geometrically different from DPE-I and DPE-II, but it still amplifies Conf 7B in the monohydrate; this conformation is favored by DPE-I and DPE-II in their helical structures. However, in the case of the QUE–PHE landscape the rigid nature of the small coformer molecule PHE prevents adoption of the helical structure for the monohydrate. The observed structure is nonporous with an alternative supramolecular synthon, synthon G. The final structure is the second anhydrate where the hitherto virtual conformation Conf 2A is expressed as also synthon I that had not been observed previously (Fig. 6). These unique selections of conformation and supramolecular synthons highlight the virtuality of conformational and synthon libraries in supersaturated solution that could selectively be fine-tuned by experimental conditions. So, in general, the QUE:PHE cocrystal landscape shows the same conformations selection: Conf 6B, Conf 5B and Conf 7B as in the previous landscapes. These conformations lead respectively to each of the three structure types: nonporous, porous and helical.

Figure 6 Selection of molecular conformation, Conf 2A, and supramolecular synthon, synthon I, in the anhydrous 2:3 QUE:PHE crystal structure.

In summary, deliberate coformer replacement is a chemical probe that may be used to perturb and understand kinetic events during crystallization that are otherwise experimentally inaccessible. The coformers TMP, 44BP, DPE-I and PHE are chemically similar but contain different geometrical features and topologies. The chemical similarity could be the factor that leads to a common conformation. The geometrical dissimilarities could be the factors that lead to a difference in stabilities between the structure types, in this case nonporous, porous and helical.¹ We note that this experimental perturbation would help one to understand the crystallization kinetics and accordingly would enter into more remote domains in the molecule to crystal landscape pathway.

3.2. Auxiliary template molecules and ternary cocrystals

This detailed understanding of quercetin cocrystal landscapes can lead one towards the isolation of stoichiometric ternary molecular solids. Very few reports discuss the synthesis of cocrystals that contain three molecules that all exist as solids at room temperature in their native crystal structures. There are only a handful of design strategies available (Aakeröy et al., 2000; Bhogala & Nangia, 2008; Thothadi & Desiraju, 2013; Seaton et al., 2013; Chakraborty et al., 2014; Dobrowolski et al., 2014). This exercise requires a good control over intermolecular interactions because there is an inherent tendency during crystallization to exclude `impurities'. In the context of quercetin cocrystal landscapes, any design strategy for ternary solids should be based on a precise selection of molecular conformations and supramolecular synthons during molecular recognition leading eventually to convergence into a modular and robust crystal structure (Sanders, 2004; Cougnon & Sanders, 2011). We utilized our understanding of the events as outlined in the earlier section and used appropriate auxiliary template molecules to reduce the molecular and supramolecular `confusion' that is inherent in a molecule like quercetin.

The design strategy for ternary solids depends upon the QUE:44BP landscape in which there are consistent appearances of Conf 5B and synthon E from the pool of possibilities. In our ternary design we exploited these robust chemical features and a 1:1 solution of QUE and 44BP in ⁱPrOH solution was layered with a saturated toluene solution of 2,2′-bis-thiophene (22TP) so that liquid diffusion takes place. The appearance of a 2:2:1 stoichiometric ternary solid with Conf 5B conformation and synthon E validated our anticipation and hints at the utility of the landscape idea in designing complex supramolecular architectures. We have shown shape and size mimicry of 22TP for 44BP in ternary solids earlier (Tothadi et al., 2011). Using this molecular mimicry as a guide leads to a well ordered QUE:44BP:22TP stoichiometric ternary solid (Fig. 7), which is not a solid solution. Tetrathiofulvalene (TTF) as a template highlights an efficient selection of one of four possible synthons, namely synthon B that is associated with Conf 6B, from the corresponding libraries in solution (Fig. 8). Both this conformation and this synthon could be termed virtual in the context of this QUE:44BP landscape because they were not observed in this system until the isolation of this particular solid. We extended this ternary design argument with the QUE:DPE-I cocrystal landscape. This exercise highlights recurring molecular conformations like Conf 5B, Conf 6B and Conf 7B in several crystal forms during landscape exploration. The shape–size mimicry of 22TP with 44BP once again acts as a guide for the selection of Conf 5B and synthon E in the prenucleation events. These precise selections in supramolecular synthesis facilitate the emergence of a porous molecular arrangement and helps to isolate a QUE:DPE-I:22TP ternary solid. Unlike the QUE:44BP:22TP ternary solid, the `longer' coformer provides a larger porous cavity in the QUE:DPE-I binary cocrystal that can efficiently accommodate a 22TP molecule that has both orientational and positional disorder in the pocket (Fig. 7). Like the TTF template in QUE:44BP, pyrene (PYR) plays a characteristic role in QUE:DPE-I for the amplification of `virtual' Conf 6B and synthon B chemical features in the ternary solid (Fig. 8).

Figure 7 Ternary design strategy. 22TP as a template molecule in QUE:44BP and QUE:DPE-I cocrystals. The presence of the robust Conf 5B conformation and supramolecular synthon, synthon E, is presented in the ternary solids. Respective guest molecules are shown.

Figure 8 Ternary design strategy. TTF (top) and PYR (lower) as template molecules in QUE:44BP and QUE:DPE-I cocrystals. These crystal structures also highlight tghe virtual selection of Conf 6B and synthon B.

We also conceptualized the role of anthracene (ANT) as a template molecule and obtained the respective 2:2:1 ternary solid (Fig. 9). This crystal structure again highlights the virtuality of conformation and synthon selection from the respective libraries. This conformation amplification in the QUE:DPE-I:ANT ternary solid is, however, different from the previously discussed virtual chemical features because neither the conformation Conf 1A or the synthon J had been observed by us previously in any of the quercetin cocrystal landscapes studied here. Accordingly we term this conformation and this synthon as being globally virtual.

Figure 9 Ternary design strategy. Anthracene (ANT) as a template molecule in QUE:DPE-I cocrystal. This solid shows a unique selection of the globally virtual Conf 1A conformation and supramolecular synthon, synthon J, in the crystal structure.

4. Conclusions

In conclusion, the isolation of different crystal forms in a quercetin cocrystal system is an illustration of combinatorial crystal synthesis in that there is an inherent selection of a particular molecular conformation and a particular supramolecular synthon in any given case. The principles of combinatorial chemistry may be profitably extended to supramolecular synthesis of solids and the ensuing events may be logically extended to the entire crystallization process prior to nucleation. The absence of concomitant crystallization of different crystal forms in any single experiment shows that the selection is quite efficient. We have recently described the formation of cocrystal polymorphs as combinatorial synthesis based solely on selection from a synthon library. Here we have extended the idea to a selection of both molecular conformation and supramolecular synthon. The convergent nature of the process is further reinforced by the use of template molecules to generate ternary cocrystals, a normally difficult task. Crystallization is known since antiquity as a purification technique which proceeds with efficient exclusion of impurities. The formation of multi-component crystals seems to fly in the face of this reality. However, a closer inspection of the events that take place in the quercetin cocrystal landscapes convey the feeling that the selection of a single conformation and a single synthon is what effectively constitutes the `purifying step' in these crystallizations. Which comes earlier, conformation selection or synthon selection, is hard to say, but formation of a multi-component crystal is then practically inevitable because of enthalpic factors that favour multi-molecular recognition. We feel that these observations open the way to synthesis of ternary and higher component molecular crystals.

Supporting information

Computing details

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

(QTMP_I)

Crystal data

C39H46N6O7	Z = 2
Mr = 710.82	F(000) = 756
Monoclinic, Pc	Dx = 1.292 Mg m^−3
a = 9.0760 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9616 (13) Å	µ = 0.09 mm^−1
c = 22.501 (3) Å	T = 150 K
β = 93.554 (7)°	Plate, yellow
V = 1826.6 (5) Å^3	0.45 × 0.25 × 0.20 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.062
Tmin = 0.728, Tmax = 1.000	θmax = 27.5°, θmin = 3.2°
18413 measured reflections	h = −11→11
8351 independent reflections	k = −11→11
6243 reflections with I > 2σ(I)	l = −29→29

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.058	w = 1/[σ^2(Fo^2) + (0.0535P)^2 + 0.2309P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.130	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.25 e Å^−3
8351 reflections	Δρmin = −0.27 e Å^−3
489 parameters	Absolute structure: Flack x determined using 2448 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
2 restraints	Absolute structure parameter: 0.5 (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
C8	0.8826 (4)	0.0812 (4)	0.34550 (18)	0.0178 (8)
C7	0.8760 (4)	0.1576 (4)	0.40202 (18)	0.0188 (8)
C6	0.7651 (4)	0.1067 (4)	0.44070 (18)	0.0173 (8)
C5	0.7471 (4)	0.1733 (4)	0.49676 (18)	0.0192 (9)
C4	0.6421 (4)	0.1195 (5)	0.53268 (18)	0.0208 (9)
H4	0.6298	0.1642	0.5703	0.025*
C3	0.5531 (4)	−0.0018 (4)	0.51364 (19)	0.0207 (9)
C2	0.5669 (4)	−0.0684 (4)	0.45846 (19)	0.0194 (9)
H2	0.5054	−0.1494	0.4455	0.023*
C1	0.6740 (4)	−0.0121 (4)	0.42305 (17)	0.0165 (8)
C9	0.7902 (4)	−0.0340 (4)	0.33065 (17)	0.0179 (8)
C10	0.7822 (4)	−0.1252 (4)	0.27634 (18)	0.0178 (8)
C15	0.6794 (4)	−0.2409 (4)	0.26898 (18)	0.0183 (9)
H15	0.6116	−0.2591	0.2987	0.022*
C14	0.6764 (4)	−0.3296 (4)	0.21811 (18)	0.0212 (9)
H14	0.6070	−0.4088	0.2136	0.025*
C13	0.7731 (4)	−0.3039 (4)	0.17409 (18)	0.0194 (9)
C12	0.8752 (4)	−0.1868 (5)	0.18089 (18)	0.0197 (9)
C11	0.8797 (4)	−0.0996 (4)	0.23135 (18)	0.0196 (9)
H11	0.9497	−0.0210	0.2358	0.024*
C17	0.1359 (4)	−0.7608 (4)	0.00901 (18)	0.0212 (9)
C18	0.0318 (4)	−0.6470 (4)	0.00060 (18)	0.0217 (9)
C19	0.2157 (4)	−0.4706 (4)	0.01387 (19)	0.0218 (9)
C20	0.3211 (4)	−0.5838 (4)	0.02283 (19)	0.0197 (9)
C21	0.0943 (5)	−0.9237 (5)	0.0057 (2)	0.0322 (11)
H21A	0.1831	−0.9850	0.0128	0.048*
H21B	0.0483	−0.9460	−0.0339	0.048*
H21C	0.0245	−0.9460	0.0360	0.048*
C22	−0.1297 (5)	−0.6791 (5)	−0.0131 (2)	0.0336 (11)
H22A	−0.1841	−0.5849	−0.0173	0.050*
H22B	−0.1678	−0.7376	0.0194	0.050*
H22C	−0.1421	−0.7358	−0.0503	0.050*
C23	0.2557 (5)	−0.3083 (5)	0.0160 (2)	0.0364 (12)
H23A	0.1663	−0.2480	0.0089	0.055*
H23B	0.3247	−0.2866	−0.0146	0.055*
H23C	0.3023	−0.2842	0.0553	0.055*
C24	0.4811 (5)	−0.5516 (5)	0.0378 (2)	0.0340 (12)
H24A	0.5357	−0.6457	0.0419	0.051*
H24B	0.4917	−0.4960	0.0753	0.051*
H24C	0.5205	−0.4920	0.0059	0.051*
C25	0.1021 (4)	−0.7706 (5)	0.16296 (19)	0.0223 (9)
C26	0.1997 (5)	−0.6507 (5)	0.17205 (19)	0.0247 (10)
C27	0.3955 (5)	−0.8129 (5)	0.18152 (19)	0.0256 (10)
C28	0.2988 (4)	−0.9346 (5)	0.17448 (19)	0.0235 (9)
C29	−0.0621 (5)	−0.7496 (5)	0.1536 (2)	0.0308 (11)
H29A	−0.1100	−0.8471	0.1483	0.046*
H29B	−0.0839	−0.6885	0.1180	0.046*
H29C	−0.0993	−0.6994	0.1883	0.046*
C30	0.1467 (5)	−0.4917 (5)	0.1725 (2)	0.0334 (11)
H30A	0.2314	−0.4247	0.1793	0.050*
H30B	0.0792	−0.4786	0.2045	0.050*
H30C	0.0949	−0.4682	0.1342	0.050*
C31	0.5587 (5)	−0.8347 (6)	0.1902 (2)	0.0387 (12)
H31A	0.6075	−0.7373	0.1939	0.058*
H31B	0.5943	−0.8883	0.1559	0.058*
H31C	0.5813	−0.8930	0.2265	0.058*
C32	0.3506 (5)	−1.0937 (5)	0.1778 (2)	0.0307 (11)
H32A	0.2656	−1.1607	0.1720	0.046*
H32B	0.4008	−1.1124	0.2169	0.046*
H32C	0.4193	−1.1119	0.1467	0.046*
C33	0.1360 (4)	−0.4939 (5)	0.33381 (18)	0.0194 (9)
C34	0.2339 (5)	−0.3767 (4)	0.34738 (19)	0.0234 (9)
C35	0.4258 (4)	−0.5416 (5)	0.35798 (19)	0.0228 (9)
C36	0.3282 (4)	−0.6607 (5)	0.34293 (18)	0.0206 (9)
C37	−0.0261 (4)	−0.4677 (5)	0.3212 (2)	0.0276 (10)
H37A	−0.0757	−0.5631	0.3127	0.041*
H37B	−0.0413	−0.4016	0.2867	0.041*
H37C	−0.0672	−0.4212	0.3559	0.041*
C38	0.1830 (5)	−0.2162 (5)	0.3490 (2)	0.0351 (12)
H38A	0.2677	−0.1513	0.3591	0.053*
H38B	0.1100	−0.2052	0.3790	0.053*
H38C	0.1382	−0.1881	0.3098	0.053*
C39	0.5891 (5)	−0.5679 (6)	0.3714 (2)	0.0379 (12)
H39A	0.6381	−0.4725	0.3806	0.057*
H39B	0.6314	−0.6129	0.3366	0.057*
H39C	0.6034	−0.6352	0.4056	0.057*
C40	0.3784 (5)	−0.8203 (5)	0.3413 (2)	0.0325 (11)
H40A	0.2939	−0.8847	0.3302	0.049*
H40B	0.4210	−0.8493	0.3807	0.049*
H40C	0.4531	−0.8311	0.3120	0.049*
N1	0.1852 (3)	−0.6341 (4)	0.33125 (15)	0.0195 (8)
N2	0.3779 (4)	−0.4011 (4)	0.35994 (16)	0.0267 (9)
N3	0.1536 (4)	−0.9117 (4)	0.16417 (15)	0.0212 (8)
N4	0.3448 (4)	−0.6726 (4)	0.18067 (17)	0.0275 (9)
N5	0.0719 (4)	−0.5037 (4)	0.00323 (16)	0.0228 (8)
N6	0.2791 (4)	−0.7272 (4)	0.02058 (16)	0.0214 (8)
O1	0.4539 (3)	−0.0475 (3)	0.55180 (14)	0.0277 (7)
O2	0.8306 (3)	0.2913 (3)	0.51516 (13)	0.0245 (7)
O3	0.9630 (3)	0.2626 (3)	0.41560 (13)	0.0248 (7)
O4	0.9866 (3)	0.1288 (3)	0.30917 (13)	0.0245 (7)
O5	0.9684 (3)	−0.1615 (3)	0.13575 (13)	0.0283 (7)
O6	0.7690 (3)	−0.3954 (3)	0.12499 (13)	0.0250 (7)
O7	0.6863 (3)	−0.0799 (3)	0.36924 (12)	0.0181 (6)
H1O	0.398 (6)	−0.144 (7)	0.538 (3)	0.066 (18)*
H4O	1.034 (5)	0.206 (6)	0.324 (2)	0.036 (14)*
H6O	0.808 (6)	−0.356 (6)	0.095 (3)	0.045 (16)*
H5O	1.034 (6)	−0.060 (7)	0.145 (3)	0.067 (19)*
H2O	0.906 (5)	0.305 (5)	0.489 (2)	0.031 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C8	0.0118 (19)	0.017 (2)	0.025 (2)	0.0017 (16)	0.0042 (16)	0.0009 (17)
C7	0.017 (2)	0.015 (2)	0.024 (2)	−0.0014 (16)	−0.0017 (16)	0.0027 (17)
C6	0.0139 (19)	0.0116 (19)	0.026 (2)	−0.0012 (15)	−0.0001 (16)	0.0013 (16)
C5	0.014 (2)	0.017 (2)	0.026 (2)	−0.0033 (16)	−0.0021 (17)	0.0006 (16)
C4	0.018 (2)	0.025 (2)	0.020 (2)	−0.0006 (17)	0.0033 (16)	−0.0049 (17)
C3	0.015 (2)	0.0157 (19)	0.031 (2)	−0.0046 (16)	0.0019 (17)	−0.0006 (17)
C2	0.016 (2)	0.0137 (19)	0.029 (2)	−0.0068 (16)	0.0008 (16)	−0.0024 (17)
C1	0.0131 (19)	0.0141 (19)	0.022 (2)	0.0034 (15)	−0.0035 (15)	0.0013 (16)
C9	0.016 (2)	0.016 (2)	0.022 (2)	−0.0001 (16)	0.0024 (17)	0.0020 (16)
C10	0.016 (2)	0.0113 (19)	0.026 (2)	0.0040 (15)	−0.0010 (16)	0.0012 (15)
C15	0.0128 (19)	0.017 (2)	0.024 (2)	0.0023 (16)	−0.0002 (16)	0.0005 (16)
C14	0.021 (2)	0.017 (2)	0.024 (2)	−0.0014 (17)	−0.0057 (17)	0.0033 (17)
C13	0.019 (2)	0.017 (2)	0.021 (2)	0.0057 (17)	−0.0040 (17)	−0.0010 (17)
C12	0.017 (2)	0.021 (2)	0.021 (2)	0.0043 (17)	0.0022 (16)	0.0061 (17)
C11	0.014 (2)	0.017 (2)	0.028 (2)	−0.0008 (16)	−0.0004 (16)	0.0026 (17)
C17	0.018 (2)	0.018 (2)	0.027 (2)	0.0001 (17)	−0.0005 (17)	−0.0005 (18)
C18	0.017 (2)	0.021 (2)	0.026 (2)	−0.0027 (17)	−0.0015 (17)	0.0023 (18)
C19	0.023 (2)	0.017 (2)	0.026 (2)	−0.0026 (17)	−0.0009 (17)	0.0008 (17)
C20	0.016 (2)	0.020 (2)	0.024 (2)	0.0013 (16)	0.0038 (17)	0.0011 (17)
C21	0.027 (3)	0.020 (2)	0.048 (3)	−0.0021 (19)	−0.004 (2)	0.001 (2)
C22	0.020 (2)	0.028 (3)	0.052 (3)	−0.0017 (19)	−0.008 (2)	0.002 (2)
C23	0.031 (3)	0.020 (2)	0.058 (3)	−0.004 (2)	−0.004 (2)	0.001 (2)
C24	0.016 (2)	0.033 (3)	0.053 (3)	−0.0020 (19)	−0.001 (2)	0.006 (2)
C25	0.021 (2)	0.025 (2)	0.022 (2)	0.0019 (18)	0.0060 (17)	0.0059 (18)
C26	0.024 (2)	0.024 (2)	0.026 (2)	0.0058 (18)	0.0033 (19)	0.0012 (18)
C27	0.018 (2)	0.032 (3)	0.026 (2)	0.0019 (18)	−0.0010 (18)	0.0017 (19)
C28	0.022 (2)	0.024 (2)	0.025 (2)	0.0017 (18)	0.0049 (18)	0.0043 (19)
C29	0.023 (2)	0.031 (3)	0.038 (3)	0.003 (2)	0.002 (2)	0.008 (2)
C30	0.034 (3)	0.025 (2)	0.041 (3)	0.005 (2)	0.002 (2)	0.000 (2)
C31	0.018 (2)	0.045 (3)	0.052 (3)	0.001 (2)	−0.004 (2)	−0.001 (2)
C32	0.025 (2)	0.027 (3)	0.040 (3)	0.0074 (19)	0.002 (2)	0.008 (2)
C33	0.014 (2)	0.024 (2)	0.020 (2)	0.0013 (17)	0.0019 (16)	0.0046 (17)
C34	0.022 (2)	0.019 (2)	0.029 (2)	0.0016 (17)	−0.0032 (18)	0.0045 (18)
C35	0.015 (2)	0.027 (2)	0.027 (2)	−0.0009 (17)	−0.0004 (17)	0.0091 (18)
C36	0.018 (2)	0.022 (2)	0.022 (2)	−0.0008 (17)	0.0058 (17)	0.0046 (17)
C37	0.017 (2)	0.030 (2)	0.036 (3)	0.0016 (18)	0.0008 (19)	0.004 (2)
C38	0.036 (3)	0.020 (2)	0.048 (3)	0.003 (2)	−0.008 (2)	0.006 (2)
C39	0.017 (2)	0.037 (3)	0.059 (3)	−0.001 (2)	−0.003 (2)	0.014 (2)
C40	0.027 (2)	0.026 (2)	0.045 (3)	0.004 (2)	0.005 (2)	0.007 (2)
N1	0.0152 (17)	0.0218 (19)	0.0218 (19)	−0.0021 (14)	0.0030 (14)	0.0044 (14)
N2	0.0197 (19)	0.024 (2)	0.036 (2)	−0.0060 (15)	−0.0061 (16)	0.0067 (16)
N3	0.0185 (18)	0.0226 (19)	0.0226 (19)	0.0023 (14)	0.0023 (15)	0.0044 (14)
N4	0.025 (2)	0.025 (2)	0.031 (2)	−0.0034 (16)	−0.0019 (17)	−0.0008 (16)
N5	0.0188 (19)	0.0167 (18)	0.032 (2)	0.0012 (14)	−0.0032 (15)	0.0017 (15)
N6	0.0208 (18)	0.0178 (18)	0.0258 (19)	0.0038 (15)	0.0032 (15)	0.0001 (15)
O1	0.0255 (17)	0.0279 (17)	0.0306 (18)	−0.0144 (14)	0.0108 (14)	−0.0072 (14)
O2	0.0242 (16)	0.0227 (15)	0.0267 (16)	−0.0129 (12)	0.0025 (13)	−0.0042 (12)
O3	0.0231 (15)	0.0219 (15)	0.0294 (16)	−0.0118 (12)	0.0016 (12)	−0.0023 (13)
O4	0.0228 (16)	0.0242 (17)	0.0271 (17)	−0.0118 (13)	0.0072 (13)	−0.0038 (13)
O5	0.0291 (17)	0.0273 (17)	0.0290 (17)	−0.0028 (14)	0.0057 (13)	−0.0006 (14)
O6	0.0313 (17)	0.0238 (17)	0.0200 (16)	−0.0011 (13)	0.0006 (13)	−0.0029 (13)
O7	0.0164 (14)	0.0160 (14)	0.0221 (15)	−0.0030 (11)	0.0016 (11)	−0.0014 (12)

Geometric parameters (Å, º)

C8—O4	1.355 (5)	C24—H24C	0.9800
C8—C9	1.359 (5)	C25—N3	1.347 (5)
C8—C7	1.449 (6)	C25—C26	1.400 (6)
C7—O3	1.253 (5)	C25—C29	1.504 (6)
C7—C6	1.445 (5)	C26—N4	1.334 (5)
C6—C1	1.391 (5)	C26—C30	1.504 (6)
C6—C5	1.414 (6)	C27—N4	1.338 (6)
C5—O2	1.350 (5)	C27—C28	1.403 (6)
C5—C4	1.374 (5)	C27—C31	1.495 (6)
C4—C3	1.405 (6)	C28—N3	1.340 (5)
C4—H4	0.9500	C28—C32	1.502 (6)
C3—O1	1.346 (5)	C29—H29A	0.9800
C3—C2	1.390 (6)	C29—H29B	0.9800
C2—C1	1.389 (5)	C29—H29C	0.9800
C2—H2	0.9500	C30—H30A	0.9800
C1—O7	1.365 (5)	C30—H30B	0.9800
C9—O7	1.383 (4)	C30—H30C	0.9800
C9—C10	1.468 (5)	C31—H31A	0.9800
C10—C15	1.398 (5)	C31—H31B	0.9800
C10—C11	1.404 (6)	C31—H31C	0.9800
C15—C14	1.393 (5)	C32—H32A	0.9800
C15—H15	0.9500	C32—H32B	0.9800
C14—C13	1.383 (6)	C32—H32C	0.9800
C14—H14	0.9500	C33—N1	1.336 (5)
C13—O6	1.374 (5)	C33—C34	1.397 (6)
C13—C12	1.402 (5)	C33—C37	1.500 (6)
C12—C11	1.377 (6)	C34—N2	1.338 (5)
C12—O5	1.381 (5)	C34—C38	1.512 (6)
C11—H11	0.9500	C35—N2	1.333 (5)
C17—N6	1.344 (5)	C35—C36	1.415 (6)
C17—C18	1.395 (6)	C35—C39	1.512 (6)
C17—C21	1.509 (6)	C36—N1	1.330 (5)
C18—N5	1.336 (5)	C36—C40	1.503 (6)
C18—C22	1.507 (6)	C37—H37A	0.9800
C19—N5	1.345 (5)	C37—H37B	0.9800
C19—C20	1.400 (6)	C37—H37C	0.9800
C19—C23	1.499 (6)	C38—H38A	0.9800
C20—N6	1.341 (5)	C38—H38B	0.9800
C20—C24	1.498 (6)	C38—H38C	0.9800
C21—H21A	0.9800	C39—H39A	0.9800
C21—H21B	0.9800	C39—H39B	0.9800
C21—H21C	0.9800	C39—H39C	0.9800
C22—H22A	0.9800	C40—H40A	0.9800
C22—H22B	0.9800	C40—H40B	0.9800
C22—H22C	0.9800	C40—H40C	0.9800
C23—H23A	0.9800	O1—H1O	1.03 (6)
C23—H23B	0.9800	O2—H2O	0.94 (5)
C23—H23C	0.9800	O4—H4O	0.87 (5)
C24—H24A	0.9800	O5—H5O	1.10 (6)
C24—H24B	0.9800	O6—H6O	0.86 (6)
O4—C8—C9	122.2 (4)	C26—C25—C29	122.5 (4)
O4—C8—C7	116.7 (3)	N4—C26—C25	121.2 (4)
C9—C8—C7	121.1 (3)	N4—C26—C30	116.9 (4)
O3—C7—C6	122.8 (4)	C25—C26—C30	121.9 (4)
O3—C7—C8	120.6 (4)	N4—C27—C28	121.1 (4)
C6—C7—C8	116.6 (3)	N4—C27—C31	117.5 (4)
C1—C6—C5	118.5 (3)	C28—C27—C31	121.4 (4)
C1—C6—C7	119.6 (3)	N3—C28—C27	120.1 (4)
C5—C6—C7	121.8 (3)	N3—C28—C32	117.1 (4)
O2—C5—C4	119.4 (4)	C27—C28—C32	122.7 (4)
O2—C5—C6	120.7 (3)	C25—C29—H29A	109.5
C4—C5—C6	119.9 (4)	C25—C29—H29B	109.5
C5—C4—C3	119.9 (4)	H29A—C29—H29B	109.5
C5—C4—H4	120.0	C25—C29—H29C	109.5
C3—C4—H4	120.0	H29A—C29—H29C	109.5
O1—C3—C2	122.7 (4)	H29B—C29—H29C	109.5
O1—C3—C4	115.8 (4)	C26—C30—H30A	109.5
C2—C3—C4	121.5 (4)	C26—C30—H30B	109.5
C1—C2—C3	117.4 (4)	H30A—C30—H30B	109.5
C1—C2—H2	121.3	C26—C30—H30C	109.5
C3—C2—H2	121.3	H30A—C30—H30C	109.5
O7—C1—C2	116.5 (3)	H30B—C30—H30C	109.5
O7—C1—C6	120.9 (3)	C27—C31—H31A	109.5
C2—C1—C6	122.6 (4)	C27—C31—H31B	109.5
C8—C9—O7	120.4 (3)	H31A—C31—H31B	109.5
C8—C9—C10	128.7 (3)	C27—C31—H31C	109.5
O7—C9—C10	110.9 (3)	H31A—C31—H31C	109.5
C15—C10—C11	118.8 (3)	H31B—C31—H31C	109.5
C15—C10—C9	120.6 (3)	C28—C32—H32A	109.5
C11—C10—C9	120.5 (3)	C28—C32—H32B	109.5
C14—C15—C10	120.0 (4)	H32A—C32—H32B	109.5
C14—C15—H15	120.0	C28—C32—H32C	109.5
C10—C15—H15	120.0	H32A—C32—H32C	109.5
C13—C14—C15	120.8 (4)	H32B—C32—H32C	109.5
C13—C14—H14	119.6	N1—C33—C34	120.5 (4)
C15—C14—H14	119.6	N1—C33—C37	117.7 (4)
O6—C13—C14	119.3 (4)	C34—C33—C37	121.8 (4)
O6—C13—C12	121.3 (4)	N2—C34—C33	121.5 (4)
C14—C13—C12	119.4 (4)	N2—C34—C38	116.6 (4)
C11—C12—O5	121.7 (4)	C33—C34—C38	121.9 (4)
C11—C12—C13	120.0 (4)	N2—C35—C36	121.3 (4)
O5—C12—C13	118.3 (4)	N2—C35—C39	117.3 (4)
C12—C11—C10	120.9 (4)	C36—C35—C39	121.4 (4)
C12—C11—H11	119.5	N1—C36—C35	120.1 (4)
C10—C11—H11	119.5	N1—C36—C40	117.3 (4)
N6—C17—C18	120.1 (4)	C35—C36—C40	122.6 (4)
N6—C17—C21	117.5 (4)	C33—C37—H37A	109.5
C18—C17—C21	122.4 (4)	C33—C37—H37B	109.5
N5—C18—C17	121.1 (4)	H37A—C37—H37B	109.5
N5—C18—C22	116.8 (4)	C33—C37—H37C	109.5
C17—C18—C22	122.0 (4)	H37A—C37—H37C	109.5
N5—C19—C20	120.8 (4)	H37B—C37—H37C	109.5
N5—C19—C23	116.7 (4)	C34—C38—H38A	109.5
C20—C19—C23	122.4 (4)	C34—C38—H38B	109.5
N6—C20—C19	119.9 (4)	H38A—C38—H38B	109.5
N6—C20—C24	117.5 (4)	C34—C38—H38C	109.5
C19—C20—C24	122.5 (4)	H38A—C38—H38C	109.5
C17—C21—H21A	109.5	H38B—C38—H38C	109.5
C17—C21—H21B	109.5	C35—C39—H39A	109.5
H21A—C21—H21B	109.5	C35—C39—H39B	109.5
C17—C21—H21C	109.5	H39A—C39—H39B	109.5
H21A—C21—H21C	109.5	C35—C39—H39C	109.5
H21B—C21—H21C	109.5	H39A—C39—H39C	109.5
C18—C22—H22A	109.5	H39B—C39—H39C	109.5
C18—C22—H22B	109.5	C36—C40—H40A	109.5
H22A—C22—H22B	109.5	C36—C40—H40B	109.5
C18—C22—H22C	109.5	H40A—C40—H40B	109.5
H22A—C22—H22C	109.5	C36—C40—H40C	109.5
H22B—C22—H22C	109.5	H40A—C40—H40C	109.5
C19—C23—H23A	109.5	H40B—C40—H40C	109.5
C19—C23—H23B	109.5	C36—N1—C33	118.9 (3)
H23A—C23—H23B	109.5	C35—N2—C34	117.7 (4)
C19—C23—H23C	109.5	C28—N3—C25	118.9 (4)
H23A—C23—H23C	109.5	C26—N4—C27	118.4 (4)
H23B—C23—H23C	109.5	C18—N5—C19	118.6 (4)
C20—C24—H24A	109.5	C20—N6—C17	119.4 (3)
C20—C24—H24B	109.5	C3—O1—H1O	114 (3)
H24A—C24—H24B	109.5	C5—O2—H2O	109 (3)
C20—C24—H24C	109.5	C8—O4—H4O	111 (3)
H24A—C24—H24C	109.5	C12—O5—H5O	110 (3)
H24B—C24—H24C	109.5	C13—O6—H6O	114 (4)
N3—C25—C26	120.1 (4)	C1—O7—C9	121.4 (3)
N3—C25—C29	117.4 (4)

(QTMP_II)

Crystal data

C31H34N4O7	Z = 4
Mr = 574.62	F(000) = 1216
Monoclinic, P21/c	Dx = 1.323 Mg m^−3
a = 15.831 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3122 (13) Å	µ = 0.10 mm^−1
c = 20.211 (3) Å	T = 150 K
β = 104.415 (7)°	Plate, yellow
V = 2885.7 (7) Å^3	0.45 × 0.40 × 0.12 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.077
Tmin = 0.821, Tmax = 1.000	θmax = 27.5°, θmin = 3.0°
22578 measured reflections	h = −20→20
6558 independent reflections	k = −12→12
4018 reflections with I > 2σ(I)	l = −26→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.163	w = 1/[σ^2(Fo^2) + (0.0734P)^2 + 1.8069P] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
6558 reflections	Δρmax = 0.32 e Å^−3
399 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
O7	0.71359 (11)	−0.07040 (17)	−0.02995 (8)	0.0167 (4)
O6	0.79097 (12)	0.0522 (2)	0.28380 (8)	0.0247 (4)
O5	0.88726 (11)	0.2441 (2)	0.22957 (8)	0.0210 (4)
O1	0.55924 (13)	−0.3277 (2)	−0.22519 (9)	0.0266 (4)
O2	0.74181 (12)	0.05103 (19)	−0.25448 (8)	0.0218 (4)
O3	0.82603 (12)	0.18958 (19)	−0.14494 (8)	0.0234 (4)
O4	0.86091 (13)	0.2338 (2)	−0.00775 (9)	0.0271 (5)
N1	0.97376 (13)	0.4223 (2)	0.15543 (10)	0.0198 (5)
N2	1.05110 (13)	0.5943 (2)	0.07598 (10)	0.0190 (5)
N3	0.42305 (14)	0.3371 (2)	−0.05778 (11)	0.0248 (5)
N4	0.50090 (13)	0.5199 (2)	−0.13237 (10)	0.0205 (5)
C7	0.79003 (16)	0.1075 (3)	−0.11043 (11)	0.0168 (5)
C6	0.73144 (15)	−0.0043 (2)	−0.14023 (11)	0.0154 (5)
C16	1.03420 (16)	0.3681 (3)	0.12561 (12)	0.0203 (5)
C12	0.83520 (15)	0.1481 (3)	0.18636 (11)	0.0161 (5)
C10	0.77477 (15)	0.0436 (2)	0.07474 (11)	0.0147 (5)
C26	0.43499 (16)	0.5672 (3)	−0.10743 (13)	0.0212 (6)
C2	0.63664 (16)	−0.2018 (3)	−0.12467 (12)	0.0180 (5)
H2	0.6127	−0.2600	−0.0952	0.022*
C13	0.78720 (16)	0.0513 (3)	0.21548 (11)	0.0175 (5)
C19	0.95242 (16)	0.5616 (3)	0.14611 (12)	0.0204 (5)
C4	0.65135 (16)	−0.1390 (3)	−0.23841 (12)	0.0181 (5)
H4	0.6364	−0.1565	−0.2862	0.022*
C8	0.80664 (16)	0.1258 (3)	−0.03700 (12)	0.0169 (5)
C32	0.40644 (19)	0.7197 (3)	−0.12155 (15)	0.0292 (6)
H32A	0.4421	0.7657	−0.1488	0.044*
H32B	0.4135	0.7713	−0.0783	0.044*
H32C	0.3450	0.7220	−0.1468	0.044*
C5	0.70798 (15)	−0.0313 (3)	−0.21204 (12)	0.0166 (5)
C9	0.76815 (15)	0.0387 (2)	0.00106 (11)	0.0158 (5)
C15	0.72792 (16)	−0.0535 (3)	0.10456 (12)	0.0193 (5)
H15	0.6917	−0.1235	0.0771	0.023*
C11	0.82822 (15)	0.1449 (3)	0.11705 (11)	0.0153 (5)
H11	0.8601	0.2122	0.0975	0.018*
C1	0.69418 (15)	−0.0917 (3)	−0.09922 (11)	0.0154 (5)
C14	0.73436 (17)	−0.0477 (3)	0.17430 (12)	0.0225 (6)
H14	0.7016	−0.1133	0.1940	0.027*
C3	0.61492 (16)	−0.2245 (3)	−0.19535 (12)	0.0179 (5)
C31	0.32062 (18)	0.5209 (3)	−0.04125 (15)	0.0346 (7)
H31A	0.3024	0.4412	−0.0164	0.052*
H31B	0.2717	0.5502	−0.0789	0.052*
H31C	0.3388	0.6022	−0.0101	0.052*
C18	0.99137 (16)	0.6492 (3)	0.10574 (12)	0.0197 (5)
C25	0.39589 (16)	0.4737 (3)	−0.06944 (13)	0.0233 (6)
C24	0.96937 (19)	0.8052 (3)	0.09556 (15)	0.0286 (6)
H24A	1.0030	0.8477	0.0658	0.043*
H24B	0.9838	0.8542	0.1399	0.043*
H24C	0.9069	0.8158	0.0743	0.043*
C23	1.14606 (17)	0.4027 (3)	0.05620 (14)	0.0269 (6)
H23A	1.1647	0.4799	0.0301	0.040*
H23B	1.1252	0.3211	0.0260	0.040*
H23C	1.1955	0.3722	0.0932	0.040*
C27	0.52894 (16)	0.3839 (3)	−0.12101 (13)	0.0221 (6)
C17	1.07375 (15)	0.4561 (3)	0.08588 (11)	0.0183 (5)
C28	0.48904 (17)	0.2916 (3)	−0.08359 (13)	0.0238 (6)
C29	0.5162 (2)	0.1371 (3)	−0.07165 (17)	0.0371 (7)
H29A	0.4805	0.0904	−0.0446	0.056*
H29B	0.5778	0.1323	−0.0469	0.056*
H29C	0.5078	0.0879	−0.1157	0.056*
C30	0.60303 (18)	0.3368 (3)	−0.14988 (15)	0.0302 (6)
H30A	0.6216	0.4172	−0.1742	0.045*
H30B	0.5839	0.2570	−0.1817	0.045*
H30C	0.6519	0.3055	−0.1127	0.045*
C22	1.05796 (19)	0.2126 (3)	0.13664 (15)	0.0296 (6)
H22A	1.0239	0.1691	0.1658	0.044*
H22B	1.1203	0.2041	0.1588	0.044*
H22C	1.0453	0.1630	0.0925	0.044*
C21	0.88591 (19)	0.6216 (3)	0.18047 (15)	0.0333 (7)
H21A	0.8661	0.5454	0.2065	0.050*
H21B	0.8361	0.6591	0.1458	0.050*
H21C	0.9123	0.6992	0.2115	0.050*
H5O	0.914 (2)	0.307 (3)	0.2056 (16)	0.040 (9)*
H1O	0.543 (2)	−0.375 (4)	−0.1923 (18)	0.057 (11)*
H4O	0.882 (2)	0.293 (4)	−0.0376 (19)	0.071 (12)*
H2O	0.781 (2)	0.115 (4)	−0.2262 (19)	0.066 (12)*
H6O	0.817 (2)	0.131 (4)	0.3047 (16)	0.045 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0217 (9)	0.0172 (9)	0.0113 (8)	−0.0057 (7)	0.0047 (7)	−0.0008 (6)
O6	0.0349 (11)	0.0298 (11)	0.0107 (8)	−0.0082 (9)	0.0083 (8)	0.0008 (8)
O5	0.0258 (10)	0.0256 (10)	0.0130 (8)	−0.0087 (8)	0.0073 (7)	−0.0038 (7)
O1	0.0352 (11)	0.0252 (10)	0.0181 (9)	−0.0132 (9)	0.0040 (8)	−0.0035 (8)
O2	0.0290 (10)	0.0241 (10)	0.0137 (8)	−0.0063 (8)	0.0079 (8)	0.0001 (7)
O3	0.0302 (10)	0.0260 (10)	0.0159 (9)	−0.0107 (8)	0.0092 (8)	0.0004 (7)
O4	0.0389 (11)	0.0293 (10)	0.0142 (9)	−0.0219 (9)	0.0088 (8)	−0.0033 (8)
N1	0.0193 (11)	0.0214 (11)	0.0187 (10)	−0.0029 (9)	0.0048 (9)	−0.0018 (9)
N2	0.0191 (11)	0.0212 (11)	0.0156 (10)	−0.0051 (9)	0.0026 (8)	−0.0005 (8)
N3	0.0210 (12)	0.0270 (12)	0.0243 (12)	−0.0017 (10)	0.0018 (9)	0.0066 (9)
N4	0.0190 (11)	0.0186 (11)	0.0218 (11)	−0.0005 (9)	0.0011 (9)	−0.0025 (9)
C7	0.0188 (12)	0.0179 (12)	0.0147 (12)	0.0016 (10)	0.0059 (10)	0.0025 (9)
C6	0.0168 (12)	0.0148 (12)	0.0155 (12)	0.0018 (10)	0.0059 (9)	0.0005 (9)
C16	0.0221 (13)	0.0206 (13)	0.0164 (12)	−0.0038 (11)	0.0013 (10)	−0.0013 (10)
C12	0.0169 (12)	0.0153 (12)	0.0155 (12)	0.0013 (10)	0.0031 (10)	−0.0013 (9)
C10	0.0160 (12)	0.0139 (12)	0.0145 (11)	0.0023 (10)	0.0041 (9)	0.0016 (9)
C26	0.0202 (13)	0.0185 (13)	0.0216 (13)	0.0006 (11)	−0.0009 (10)	−0.0030 (10)
C2	0.0201 (13)	0.0183 (13)	0.0164 (12)	−0.0021 (10)	0.0059 (10)	0.0028 (10)
C13	0.0221 (13)	0.0198 (13)	0.0113 (11)	0.0019 (11)	0.0056 (10)	0.0019 (9)
C19	0.0170 (12)	0.0223 (14)	0.0217 (13)	−0.0041 (11)	0.0042 (10)	−0.0051 (10)
C4	0.0228 (13)	0.0189 (13)	0.0126 (11)	0.0021 (11)	0.0042 (10)	−0.0009 (9)
C8	0.0203 (13)	0.0169 (12)	0.0146 (11)	−0.0045 (10)	0.0065 (10)	−0.0007 (9)
C32	0.0288 (15)	0.0217 (14)	0.0347 (16)	0.0031 (12)	0.0034 (12)	−0.0020 (12)
C5	0.0190 (12)	0.0169 (12)	0.0156 (12)	0.0039 (10)	0.0072 (10)	0.0018 (9)
C9	0.0174 (12)	0.0149 (12)	0.0143 (11)	0.0005 (10)	0.0022 (9)	−0.0006 (9)
C15	0.0230 (13)	0.0189 (13)	0.0161 (12)	−0.0054 (11)	0.0049 (10)	−0.0002 (10)
C11	0.0147 (12)	0.0168 (12)	0.0148 (11)	−0.0005 (10)	0.0043 (9)	0.0035 (9)
C1	0.0161 (12)	0.0184 (12)	0.0111 (11)	0.0050 (10)	0.0024 (9)	−0.0004 (9)
C14	0.0268 (14)	0.0217 (13)	0.0202 (13)	−0.0046 (11)	0.0084 (11)	0.0064 (10)
C3	0.0207 (13)	0.0150 (12)	0.0160 (12)	−0.0001 (10)	0.0007 (10)	−0.0006 (9)
C31	0.0256 (15)	0.0445 (18)	0.0349 (16)	0.0010 (14)	0.0098 (13)	−0.0011 (14)
C18	0.0186 (13)	0.0204 (13)	0.0191 (12)	−0.0025 (11)	0.0025 (10)	−0.0035 (10)
C25	0.0175 (13)	0.0290 (15)	0.0208 (13)	−0.0008 (11)	0.0001 (10)	−0.0025 (11)
C24	0.0293 (15)	0.0225 (14)	0.0347 (15)	−0.0002 (12)	0.0093 (12)	0.0002 (12)
C23	0.0246 (14)	0.0316 (16)	0.0260 (14)	0.0003 (12)	0.0091 (11)	−0.0039 (12)
C27	0.0195 (13)	0.0228 (14)	0.0210 (13)	−0.0015 (11)	−0.0005 (10)	−0.0027 (10)
C17	0.0154 (12)	0.0231 (14)	0.0147 (12)	−0.0035 (10)	0.0006 (9)	−0.0018 (10)
C28	0.0226 (14)	0.0188 (14)	0.0259 (14)	0.0001 (11)	−0.0018 (11)	0.0030 (10)
C29	0.0351 (17)	0.0221 (15)	0.0512 (19)	0.0050 (13)	0.0055 (15)	0.0114 (13)
C30	0.0269 (15)	0.0297 (16)	0.0345 (16)	0.0044 (13)	0.0086 (12)	−0.0019 (13)
C22	0.0314 (15)	0.0242 (15)	0.0333 (16)	0.0015 (12)	0.0082 (12)	0.0075 (12)
C21	0.0301 (16)	0.0335 (16)	0.0420 (17)	−0.0027 (13)	0.0196 (14)	−0.0087 (13)

Geometric parameters (Å, º)

O7—C1	1.371 (3)	C19—C21	1.505 (4)
O7—C9	1.379 (3)	C4—C5	1.363 (3)
O6—C13	1.367 (3)	C4—C3	1.405 (3)
O6—H6O	0.90 (3)	C4—H4	0.9500
O5—C12	1.372 (3)	C8—C9	1.362 (3)
O5—H5O	0.92 (3)	C32—H32A	0.9800
O1—C3	1.342 (3)	C32—H32B	0.9800
O1—H1O	0.89 (4)	C32—H32C	0.9800
O2—C5	1.356 (3)	C15—C14	1.389 (3)
O2—H2O	0.94 (4)	C15—H15	0.9500
O3—C7	1.262 (3)	C11—H11	0.9500
O4—C8	1.358 (3)	C14—H14	0.9500
O4—H4O	0.94 (4)	C31—C25	1.509 (4)
N1—C19	1.342 (3)	C31—H31A	0.9800
N1—C16	1.350 (3)	C31—H31B	0.9800
N2—C17	1.337 (3)	C31—H31C	0.9800
N2—C18	1.342 (3)	C18—C24	1.496 (4)
N3—C25	1.344 (3)	C24—H24A	0.9800
N3—C28	1.347 (3)	C24—H24B	0.9800
N4—C26	1.341 (3)	C24—H24C	0.9800
N4—C27	1.342 (3)	C23—C17	1.503 (3)
C7—C6	1.425 (3)	C23—H23A	0.9800
C7—C8	1.451 (3)	C23—H23B	0.9800
C6—C1	1.393 (3)	C23—H23C	0.9800
C6—C5	1.428 (3)	C27—C28	1.396 (4)
C16—C17	1.400 (3)	C27—C30	1.500 (4)
C16—C22	1.499 (4)	C28—C29	1.503 (4)
C12—C11	1.378 (3)	C29—H29A	0.9800
C12—C13	1.399 (3)	C29—H29B	0.9800
C10—C15	1.398 (3)	C29—H29C	0.9800
C10—C11	1.406 (3)	C30—H30A	0.9800
C10—C9	1.467 (3)	C30—H30B	0.9800
C26—C25	1.403 (4)	C30—H30C	0.9800
C26—C32	1.496 (4)	C22—H22A	0.9800
C2—C1	1.383 (3)	C22—H22B	0.9800
C2—C3	1.400 (3)	C22—H22C	0.9800
C2—H2	0.9500	C21—H21A	0.9800
C13—C14	1.377 (3)	C21—H21B	0.9800
C19—C18	1.401 (3)	C21—H21C	0.9800
C1—O7—C9	121.77 (18)	C13—C14—C15	121.3 (2)
C13—O6—H6O	112 (2)	C13—C14—H14	119.3
C12—O5—H5O	110.9 (19)	C15—C14—H14	119.3
C3—O1—H1O	107 (2)	O1—C3—C2	122.3 (2)
C5—O2—H2O	106 (2)	O1—C3—C4	116.9 (2)
C8—O4—H4O	116 (2)	C2—C3—C4	120.8 (2)
C19—N1—C16	118.7 (2)	C25—C31—H31A	109.5
C17—N2—C18	119.5 (2)	C25—C31—H31B	109.5
C25—N3—C28	118.4 (2)	H31A—C31—H31B	109.5
C26—N4—C27	120.0 (2)	C25—C31—H31C	109.5
O3—C7—C6	123.0 (2)	H31A—C31—H31C	109.5
O3—C7—C8	120.1 (2)	H31B—C31—H31C	109.5
C6—C7—C8	116.8 (2)	N2—C18—C19	120.1 (2)
C1—C6—C7	120.2 (2)	N2—C18—C24	118.3 (2)
C1—C6—C5	117.4 (2)	C19—C18—C24	121.6 (2)
C7—C6—C5	122.4 (2)	N3—C25—C26	121.2 (2)
N1—C16—C17	120.3 (2)	N3—C25—C31	117.3 (2)
N1—C16—C22	118.3 (2)	C26—C25—C31	121.6 (2)
C17—C16—C22	121.3 (2)	C18—C24—H24A	109.5
O5—C12—C11	123.0 (2)	C18—C24—H24B	109.5
O5—C12—C13	117.1 (2)	H24A—C24—H24B	109.5
C11—C12—C13	119.9 (2)	C18—C24—H24C	109.5
C15—C10—C11	118.4 (2)	H24A—C24—H24C	109.5
C15—C10—C9	120.4 (2)	H24B—C24—H24C	109.5
C11—C10—C9	121.2 (2)	C17—C23—H23A	109.5
N4—C26—C25	119.5 (2)	C17—C23—H23B	109.5
N4—C26—C32	117.8 (2)	H23A—C23—H23B	109.5
C25—C26—C32	122.7 (2)	C17—C23—H23C	109.5
C1—C2—C3	117.6 (2)	H23A—C23—H23C	109.5
C1—C2—H2	121.2	H23B—C23—H23C	109.5
C3—C2—H2	121.2	N4—C27—C28	119.9 (2)
O6—C13—C14	118.8 (2)	N4—C27—C30	117.8 (2)
O6—C13—C12	121.9 (2)	C28—C27—C30	122.3 (2)
C14—C13—C12	119.3 (2)	N2—C17—C16	120.5 (2)
N1—C19—C18	120.8 (2)	N2—C17—C23	117.5 (2)
N1—C19—C21	118.3 (2)	C16—C17—C23	121.9 (2)
C18—C19—C21	120.9 (2)	N3—C28—C27	121.0 (2)
C5—C4—C3	120.4 (2)	N3—C28—C29	117.2 (2)
C5—C4—H4	119.8	C27—C28—C29	121.8 (3)
C3—C4—H4	119.8	C28—C29—H29A	109.5
O4—C8—C9	121.2 (2)	C28—C29—H29B	109.5
O4—C8—C7	117.8 (2)	H29A—C29—H29B	109.5
C9—C8—C7	121.0 (2)	C28—C29—H29C	109.5
C26—C32—H32A	109.5	H29A—C29—H29C	109.5
C26—C32—H32B	109.5	H29B—C29—H29C	109.5
H32A—C32—H32B	109.5	C27—C30—H30A	109.5
C26—C32—H32C	109.5	C27—C30—H30B	109.5
H32A—C32—H32C	109.5	H30A—C30—H30B	109.5
H32B—C32—H32C	109.5	C27—C30—H30C	109.5
O2—C5—C4	119.6 (2)	H30A—C30—H30C	109.5
O2—C5—C6	120.0 (2)	H30B—C30—H30C	109.5
C4—C5—C6	120.4 (2)	C16—C22—H22A	109.5
C8—C9—O7	120.0 (2)	C16—C22—H22B	109.5
C8—C9—C10	128.7 (2)	H22A—C22—H22B	109.5
O7—C9—C10	111.25 (19)	C16—C22—H22C	109.5
C14—C15—C10	120.0 (2)	H22A—C22—H22C	109.5
C14—C15—H15	120.0	H22B—C22—H22C	109.5
C10—C15—H15	120.0	C19—C21—H21A	109.5
C12—C11—C10	121.1 (2)	C19—C21—H21B	109.5
C12—C11—H11	119.4	H21A—C21—H21B	109.5
C10—C11—H11	119.4	C19—C21—H21C	109.5
O7—C1—C2	116.5 (2)	H21A—C21—H21C	109.5
O7—C1—C6	120.2 (2)	H21B—C21—H21C	109.5
C2—C1—C6	123.3 (2)
O3—C7—C6—C1	179.7 (2)	C9—O7—C1—C6	1.6 (3)
C8—C7—C6—C1	−1.1 (3)	C3—C2—C1—O7	179.2 (2)
O3—C7—C6—C5	−0.7 (4)	C3—C2—C1—C6	−0.5 (4)
C8—C7—C6—C5	178.4 (2)	C7—C6—C1—O7	0.1 (3)
C19—N1—C16—C17	0.1 (3)	C5—C6—C1—O7	−179.5 (2)
C19—N1—C16—C22	179.7 (2)	C7—C6—C1—C2	179.8 (2)
C27—N4—C26—C25	0.1 (3)	C5—C6—C1—C2	0.2 (3)
C27—N4—C26—C32	179.9 (2)	O6—C13—C14—C15	180.0 (2)
O5—C12—C13—O6	0.5 (3)	C12—C13—C14—C15	0.1 (4)
C11—C12—C13—O6	−178.9 (2)	C10—C15—C14—C13	−0.9 (4)
O5—C12—C13—C14	−179.6 (2)	C1—C2—C3—O1	−179.5 (2)
C11—C12—C13—C14	1.0 (4)	C1—C2—C3—C4	0.7 (4)
C16—N1—C19—C18	0.6 (3)	C5—C4—C3—O1	179.5 (2)
C16—N1—C19—C21	−179.1 (2)	C5—C4—C3—C2	−0.7 (4)
O3—C7—C8—O4	0.6 (4)	C17—N2—C18—C19	−0.8 (3)
C6—C7—C8—O4	−178.7 (2)	C17—N2—C18—C24	178.1 (2)
O3—C7—C8—C9	179.7 (2)	N1—C19—C18—N2	−0.3 (4)
C6—C7—C8—C9	0.5 (3)	C21—C19—C18—N2	179.4 (2)
C3—C4—C5—O2	−179.3 (2)	N1—C19—C18—C24	−179.1 (2)
C3—C4—C5—C6	0.4 (4)	C21—C19—C18—C24	0.5 (4)
C1—C6—C5—O2	179.6 (2)	C28—N3—C25—C26	−0.1 (4)
C7—C6—C5—O2	0.0 (3)	C28—N3—C25—C31	178.7 (2)
C1—C6—C5—C4	−0.1 (3)	N4—C26—C25—N3	−0.3 (4)
C7—C6—C5—C4	−179.7 (2)	C32—C26—C25—N3	179.9 (2)
O4—C8—C9—O7	−179.7 (2)	N4—C26—C25—C31	−179.0 (2)
C7—C8—C9—O7	1.1 (4)	C32—C26—C25—C31	1.2 (4)
O4—C8—C9—C10	1.2 (4)	C26—N4—C27—C28	0.4 (3)
C7—C8—C9—C10	−177.9 (2)	C26—N4—C27—C30	−179.8 (2)
C1—O7—C9—C8	−2.2 (3)	C18—N2—C17—C16	1.5 (3)
C1—O7—C9—C10	176.97 (19)	C18—N2—C17—C23	−175.2 (2)
C15—C10—C9—C8	178.2 (2)	N1—C16—C17—N2	−1.2 (3)
C11—C10—C9—C8	−2.1 (4)	C22—C16—C17—N2	179.3 (2)
C15—C10—C9—O7	−0.9 (3)	N1—C16—C17—C23	175.3 (2)
C11—C10—C9—O7	178.8 (2)	C22—C16—C17—C23	−4.2 (4)
C11—C10—C15—C14	0.5 (4)	C25—N3—C28—C27	0.6 (4)
C9—C10—C15—C14	−179.7 (2)	C25—N3—C28—C29	−178.1 (2)
O5—C12—C11—C10	179.3 (2)	N4—C27—C28—N3	−0.8 (4)
C13—C12—C11—C10	−1.3 (4)	C30—C27—C28—N3	179.5 (2)
C15—C10—C11—C12	0.6 (3)	N4—C27—C28—C29	177.9 (2)
C9—C10—C11—C12	−179.2 (2)	C30—C27—C28—C29	−1.9 (4)
C9—O7—C1—C2	−178.1 (2)

(QTMP_III)

Crystal data

C27H30N2O9	V = 1274.26 (17) Å^3
Mr = 526.53	Z = 2
Triclinic, P1	F(000) = 556
a = 9.3506 (7) Å	Dx = 1.372 Mg m^−3
b = 10.9120 (8) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.002 (1) Å	µ = 0.10 mm^−1
α = 76.798 (5)°	T = 150 K
β = 84.048 (6)°	Plate, yellow
γ = 81.580 (6)°	0.40 × 0.40 × 0.15 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.034
Tmin = 0.752, Tmax = 1.000	θmax = 27.5°, θmin = 3.1°
13650 measured reflections	h = −12→12
5832 independent reflections	k = −14→14
4470 reflections with I > 2σ(I)	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.159	w = 1/[σ^2(Fo^2) + (0.0967P)^2 + 0.5735P] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
5832 reflections	Δρmax = 0.29 e Å^−3
363 parameters	Δρmin = −0.39 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
H2O	0.401 (3)	−0.039 (2)	0.245 (2)	0.049 (7)*
H4O	0.393 (3)	0.014 (3)	−0.071 (2)	0.063 (8)*
H6O	−0.278 (3)	0.361 (3)	−0.385 (2)	0.064 (8)*
H1O	−0.159 (3)	0.229 (3)	0.404 (2)	0.063 (8)*
H5O	0.009 (2)	0.184 (2)	−0.4441 (19)	0.036 (6)*
O7	−0.00089 (12)	0.15555 (11)	0.06354 (8)	0.0189 (3)
O3	0.40478 (12)	−0.03076 (12)	0.10536 (9)	0.0239 (3)
O6	−0.19940 (13)	0.30927 (12)	−0.39807 (9)	0.0263 (3)
O5	0.06944 (13)	0.17310 (12)	−0.40176 (9)	0.0255 (3)
O1	−0.07879 (14)	0.17774 (12)	0.42433 (9)	0.0269 (3)
O2	0.36444 (13)	−0.02698 (12)	0.30596 (10)	0.0245 (3)
C9	0.08455 (17)	0.12474 (15)	−0.02195 (12)	0.0171 (3)
O4	0.30582 (13)	0.02676 (13)	−0.09031 (9)	0.0277 (3)
C6	0.18581 (16)	0.06154 (14)	0.18050 (12)	0.0170 (3)
C1	0.04779 (17)	0.12647 (14)	0.16239 (12)	0.0171 (3)
C7	0.27708 (16)	0.02602 (15)	0.09456 (12)	0.0179 (3)
C2	−0.04529 (17)	0.16701 (15)	0.24132 (12)	0.0203 (3)
H2	−0.1387	0.2114	0.2268	0.024*
N1	−0.55404 (15)	0.52338 (13)	0.36960 (11)	0.0231 (3)
C11	0.07365 (17)	0.14958 (15)	−0.21765 (12)	0.0176 (3)
H11	0.1667	0.1016	−0.2211	0.021*
C8	0.21964 (17)	0.06006 (15)	−0.00806 (12)	0.0186 (3)
C10	0.01099 (17)	0.17223 (14)	−0.11973 (12)	0.0171 (3)
C4	0.14063 (18)	0.07395 (15)	0.36523 (12)	0.0204 (3)
H4	0.1711	0.0561	0.4352	0.025*
N2	−0.31543 (15)	0.34390 (13)	0.37044 (11)	0.0235 (3)
C3	0.00312 (18)	0.14028 (15)	0.34273 (12)	0.0201 (3)
C5	0.23074 (17)	0.03510 (14)	0.28527 (12)	0.0182 (3)
C14	−0.19908 (18)	0.28815 (16)	−0.20867 (13)	0.0239 (4)
H14	−0.2927	0.3352	−0.2053	0.029*
C12	0.00213 (17)	0.19592 (15)	−0.30880 (12)	0.0183 (3)
C18	−0.56997 (19)	0.39977 (17)	0.39218 (13)	0.0253 (4)
C13	−0.13595 (17)	0.26644 (15)	−0.30524 (12)	0.0195 (3)
C17	−0.42143 (18)	0.55876 (16)	0.34363 (13)	0.0229 (4)
C16	−0.29984 (18)	0.46761 (16)	0.34386 (14)	0.0251 (4)
C15	−0.12719 (18)	0.24204 (16)	−0.11715 (13)	0.0215 (3)
H15	−0.1721	0.2579	−0.0517	0.026*
C19	−0.44805 (19)	0.30829 (16)	0.39407 (13)	0.0246 (4)
C23	−0.4586 (2)	0.16842 (18)	0.42178 (18)	0.0381 (5)
H23A	−0.3612	0.1213	0.4183	0.057*
H23B	−0.5171	0.1473	0.3715	0.057*
H23C	−0.5042	0.1453	0.4937	0.057*
C21	−0.4110 (2)	0.69836 (17)	0.31353 (17)	0.0348 (4)
H21A	−0.5081	0.7456	0.3189	0.052*
H21B	−0.3686	0.7203	0.2406	0.052*
H21C	−0.3495	0.7205	0.3614	0.052*
C20	−0.1486 (2)	0.5019 (2)	0.3161 (2)	0.0419 (5)
H20A	−0.0798	0.4243	0.3207	0.063*
H20B	−0.1255	0.5504	0.3657	0.063*
H20C	−0.1420	0.5535	0.2438	0.063*
C22	−0.7217 (2)	0.3655 (2)	0.41336 (19)	0.0405 (5)
H22A	−0.7907	0.4431	0.4083	0.061*
H22B	−0.7327	0.3120	0.4846	0.061*
H22C	−0.7408	0.3191	0.3610	0.061*
C25	0.4750 (4)	0.3027 (3)	0.1093 (3)	0.0719 (9)
H25A	0.4414	0.2218	0.1486	0.086*
H25B	0.5761	0.3020	0.1259	0.086*
C26	0.2419 (4)	0.4077 (3)	0.1167 (3)	0.0761 (10)
H26A	0.1799	0.4807	0.1382	0.091*
H26B	0.2036	0.3290	0.1563	0.091*
O9	0.3858 (3)	0.40578 (19)	0.14219 (16)	0.0746 (7)
O8	0.3266 (3)	0.3163 (2)	−0.03274 (17)	0.0784 (7)
C24	0.4703 (4)	0.3132 (3)	−0.0064 (3)	0.0703 (9)
H24A	0.5095	0.3915	−0.0458	0.084*
H24B	0.5318	0.2399	−0.0276	0.084*
C27	0.2367 (4)	0.4181 (3)	0.0017 (3)	0.0825 (10)
H27A	0.1356	0.4179	−0.0144	0.099*
H27B	0.2689	0.4996	−0.0375	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0173 (5)	0.0259 (6)	0.0129 (5)	0.0035 (4)	−0.0023 (4)	−0.0062 (4)
O3	0.0159 (6)	0.0330 (7)	0.0206 (6)	0.0025 (5)	−0.0016 (5)	−0.0050 (5)
O6	0.0245 (6)	0.0350 (7)	0.0166 (6)	0.0089 (5)	−0.0054 (5)	−0.0059 (5)
O5	0.0204 (6)	0.0416 (7)	0.0140 (6)	0.0027 (5)	−0.0014 (5)	−0.0089 (5)
O1	0.0271 (7)	0.0352 (7)	0.0164 (6)	0.0115 (5)	−0.0041 (5)	−0.0103 (5)
O2	0.0197 (6)	0.0314 (7)	0.0199 (6)	0.0073 (5)	−0.0057 (5)	−0.0053 (5)
C9	0.0171 (7)	0.0192 (7)	0.0154 (7)	−0.0023 (6)	0.0003 (6)	−0.0054 (6)
O4	0.0164 (6)	0.0471 (8)	0.0183 (6)	0.0060 (5)	−0.0014 (5)	−0.0110 (5)
C6	0.0171 (7)	0.0164 (7)	0.0178 (7)	−0.0027 (6)	−0.0017 (6)	−0.0040 (6)
C1	0.0195 (8)	0.0167 (7)	0.0151 (7)	−0.0010 (6)	−0.0043 (6)	−0.0027 (6)
C7	0.0148 (7)	0.0182 (7)	0.0205 (8)	−0.0025 (6)	−0.0018 (6)	−0.0032 (6)
C2	0.0188 (8)	0.0230 (8)	0.0190 (8)	0.0044 (6)	−0.0037 (6)	−0.0079 (6)
N1	0.0227 (7)	0.0251 (7)	0.0201 (7)	0.0025 (6)	−0.0036 (6)	−0.0046 (5)
C11	0.0154 (7)	0.0197 (7)	0.0175 (7)	−0.0010 (6)	−0.0014 (6)	−0.0043 (6)
C8	0.0167 (7)	0.0234 (8)	0.0161 (7)	−0.0022 (6)	0.0007 (6)	−0.0060 (6)
C10	0.0173 (7)	0.0178 (7)	0.0163 (7)	−0.0027 (6)	−0.0020 (6)	−0.0035 (6)
C4	0.0235 (8)	0.0210 (8)	0.0164 (7)	0.0022 (6)	−0.0064 (6)	−0.0043 (6)
N2	0.0249 (7)	0.0226 (7)	0.0224 (7)	0.0022 (6)	−0.0034 (6)	−0.0062 (6)
C3	0.0224 (8)	0.0199 (8)	0.0175 (7)	0.0013 (6)	−0.0006 (6)	−0.0059 (6)
C5	0.0175 (7)	0.0164 (7)	0.0196 (8)	0.0007 (6)	−0.0037 (6)	−0.0026 (6)
C14	0.0201 (8)	0.0292 (9)	0.0201 (8)	0.0057 (7)	−0.0029 (6)	−0.0059 (7)
C12	0.0188 (8)	0.0209 (8)	0.0158 (7)	−0.0035 (6)	0.0012 (6)	−0.0054 (6)
C18	0.0236 (8)	0.0283 (9)	0.0234 (8)	−0.0017 (7)	−0.0045 (7)	−0.0045 (7)
C13	0.0194 (8)	0.0226 (8)	0.0160 (7)	−0.0009 (6)	−0.0029 (6)	−0.0032 (6)
C17	0.0231 (8)	0.0223 (8)	0.0223 (8)	0.0008 (6)	−0.0020 (7)	−0.0049 (6)
C16	0.0227 (8)	0.0242 (8)	0.0276 (9)	0.0002 (7)	−0.0006 (7)	−0.0066 (7)
C15	0.0200 (8)	0.0266 (8)	0.0172 (7)	0.0025 (6)	−0.0007 (6)	−0.0072 (6)
C19	0.0271 (9)	0.0243 (8)	0.0236 (8)	−0.0012 (7)	−0.0057 (7)	−0.0070 (6)
C23	0.0411 (11)	0.0247 (10)	0.0481 (12)	−0.0042 (8)	−0.0063 (10)	−0.0056 (8)
C21	0.0325 (10)	0.0228 (9)	0.0452 (11)	−0.0001 (8)	−0.0023 (9)	−0.0019 (8)
C20	0.0256 (10)	0.0337 (11)	0.0627 (14)	−0.0024 (8)	0.0055 (10)	−0.0077 (10)
C22	0.0266 (10)	0.0409 (12)	0.0528 (13)	−0.0071 (8)	−0.0014 (9)	−0.0067 (10)
C25	0.081 (2)	0.0552 (17)	0.080 (2)	−0.0285 (16)	0.0148 (17)	−0.0122 (15)
C26	0.085 (2)	0.0514 (16)	0.101 (3)	−0.0333 (16)	0.0383 (19)	−0.0389 (16)
O9	0.1090 (17)	0.0654 (13)	0.0628 (12)	−0.0511 (12)	0.0260 (12)	−0.0307 (10)
O8	0.1057 (17)	0.0691 (14)	0.0771 (14)	−0.0462 (13)	0.0217 (13)	−0.0403 (11)
C24	0.083 (2)	0.0509 (16)	0.083 (2)	−0.0355 (15)	0.0362 (17)	−0.0286 (14)
C27	0.088 (2)	0.0623 (19)	0.105 (3)	−0.0309 (18)	0.000 (2)	−0.0219 (18)

Geometric parameters (Å, º)

O7—C1	1.3610 (18)	C14—H14	0.9500
O7—C9	1.3764 (18)	C12—C13	1.405 (2)
O3—C7	1.2680 (19)	C18—C19	1.399 (2)
O6—C13	1.3553 (19)	C18—C22	1.502 (3)
O6—H6O	0.88 (3)	C17—C16	1.396 (2)
O5—C12	1.3612 (18)	C17—C21	1.499 (2)
O5—H5O	0.80 (2)	C16—C20	1.502 (3)
O1—C3	1.3481 (19)	C15—H15	0.9500
O1—H1O	0.90 (3)	C19—C23	1.501 (3)
O2—C5	1.3538 (18)	C23—H23A	0.9800
O2—H2O	0.87 (3)	C23—H23B	0.9800
C9—C8	1.362 (2)	C23—H23C	0.9800
C9—C10	1.461 (2)	C21—H21A	0.9800
O4—C8	1.3557 (18)	C21—H21B	0.9800
O4—H4O	0.86 (3)	C21—H21C	0.9800
C6—C1	1.394 (2)	C20—H20A	0.9800
C6—C5	1.421 (2)	C20—H20B	0.9800
C6—C7	1.425 (2)	C20—H20C	0.9800
C1—C2	1.384 (2)	C22—H22A	0.9800
C7—C8	1.439 (2)	C22—H22B	0.9800
C2—C3	1.392 (2)	C22—H22C	0.9800
C2—H2	0.9500	C25—O9	1.420 (4)
N1—C17	1.340 (2)	C25—C24	1.487 (5)
N1—C18	1.340 (2)	C25—H25A	0.9900
C11—C12	1.378 (2)	C25—H25B	0.9900
C11—C10	1.404 (2)	C26—O9	1.415 (4)
C11—H11	0.9500	C26—C27	1.480 (5)
C10—C15	1.402 (2)	C26—H26A	0.9900
C4—C5	1.373 (2)	C26—H26B	0.9900
C4—C3	1.404 (2)	O8—C24	1.414 (4)
C4—H4	0.9500	O8—C27	1.420 (4)
N2—C19	1.338 (2)	C24—H24A	0.9900
N2—C16	1.341 (2)	C24—H24B	0.9900
C14—C15	1.384 (2)	C27—H27A	0.9900
C14—C13	1.386 (2)	C27—H27B	0.9900
C1—O7—C9	121.61 (12)	C17—C16—C20	122.60 (16)
C13—O6—H6O	106.6 (18)	C14—C15—C10	120.89 (15)
C12—O5—H5O	108.4 (16)	C14—C15—H15	119.6
C3—O1—H1O	112.4 (18)	C10—C15—H15	119.6
C5—O2—H2O	103.4 (17)	N2—C19—C18	120.17 (16)
C8—C9—O7	119.95 (13)	N2—C19—C23	117.24 (16)
C8—C9—C10	128.94 (14)	C18—C19—C23	122.59 (17)
O7—C9—C10	111.10 (12)	C19—C23—H23A	109.5
C8—O4—H4O	106.3 (19)	C19—C23—H23B	109.5
C1—C6—C5	117.88 (14)	H23A—C23—H23B	109.5
C1—C6—C7	119.64 (14)	C19—C23—H23C	109.5
C5—C6—C7	122.47 (14)	H23A—C23—H23C	109.5
O7—C1—C2	116.49 (13)	H23B—C23—H23C	109.5
O7—C1—C6	120.62 (14)	C17—C21—H21A	109.5
C2—C1—C6	122.88 (14)	C17—C21—H21B	109.5
O3—C7—C6	122.72 (14)	H21A—C21—H21B	109.5
O3—C7—C8	120.19 (14)	C17—C21—H21C	109.5
C6—C7—C8	117.07 (13)	H21A—C21—H21C	109.5
C1—C2—C3	117.53 (14)	H21B—C21—H21C	109.5
C1—C2—H2	121.2	C16—C20—H20A	109.5
C3—C2—H2	121.2	C16—C20—H20B	109.5
C17—N1—C18	119.53 (14)	H20A—C20—H20B	109.5
C12—C11—C10	120.97 (14)	C16—C20—H20C	109.5
C12—C11—H11	119.5	H20A—C20—H20C	109.5
C10—C11—H11	119.5	H20B—C20—H20C	109.5
O4—C8—C9	121.45 (14)	C18—C22—H22A	109.5
O4—C8—C7	117.46 (13)	C18—C22—H22B	109.5
C9—C8—C7	121.09 (14)	H22A—C22—H22B	109.5
C15—C10—C11	118.08 (14)	C18—C22—H22C	109.5
C15—C10—C9	119.77 (14)	H22A—C22—H22C	109.5
C11—C10—C9	122.15 (14)	H22B—C22—H22C	109.5
C5—C4—C3	119.43 (14)	O9—C25—C24	110.7 (3)
C5—C4—H4	120.3	O9—C25—H25A	109.5
C3—C4—H4	120.3	C24—C25—H25A	109.5
C19—N2—C16	119.76 (14)	O9—C25—H25B	109.5
O1—C3—C2	121.85 (14)	C24—C25—H25B	109.5
O1—C3—C4	116.41 (14)	H25A—C25—H25B	108.1
C2—C3—C4	121.73 (14)	O9—C26—C27	110.5 (3)
O2—C5—C4	119.78 (14)	O9—C26—H26A	109.5
O2—C5—C6	119.68 (14)	C27—C26—H26A	109.5
C4—C5—C6	120.53 (14)	O9—C26—H26B	109.5
C15—C14—C13	120.71 (15)	C27—C26—H26B	109.5
C15—C14—H14	119.6	H26A—C26—H26B	108.1
C13—C14—H14	119.6	C26—O9—C25	109.4 (2)
O5—C12—C11	118.35 (14)	C24—O8—C27	109.7 (2)
O5—C12—C13	121.26 (14)	O8—C24—C25	110.8 (2)
C11—C12—C13	120.38 (14)	O8—C24—H24A	109.5
N1—C18—C19	120.09 (16)	C25—C24—H24A	109.5
N1—C18—C22	117.43 (16)	O8—C24—H24B	109.5
C19—C18—C22	122.48 (17)	C25—C24—H24B	109.5
O6—C13—C14	123.98 (14)	H24A—C24—H24B	108.1
O6—C13—C12	117.05 (14)	O8—C27—C26	111.4 (3)
C14—C13—C12	118.97 (14)	O8—C27—H27A	109.4
N1—C17—C16	120.38 (15)	C26—C27—H27A	109.4
N1—C17—C21	117.19 (15)	O8—C27—H27B	109.4
C16—C17—C21	122.43 (16)	C26—C27—H27B	109.4
N2—C16—C17	119.99 (16)	H27A—C27—H27B	108.0
N2—C16—C20	117.41 (15)

(QTMP_IV)

Crystal data

C27H30N2O8	V = 1266.0 (2) Å^3
Mr = 510.53	Z = 2
Triclinic, P1	F(000) = 540
a = 9.3202 (10) Å	Dx = 1.339 Mg m^−3
b = 10.7538 (12) Å	Mo Kα radiation, λ = 0.71073 Å
c = 12.9869 (14) Å	µ = 0.10 mm^−1
α = 79.471 (6)°	T = 150 K
β = 85.133 (6)°	Plate, yellow
γ = 82.377 (6)°	0.60 × 0.40 × 0.15 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.030
Tmin = 0.844, Tmax = 1.000	θmax = 27.5°, θmin = 3.1°
13412 measured reflections	h = −12→11
5779 independent reflections	k = −13→13
4277 reflections with I > 2σ(I)	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.070	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.202	w = 1/[σ^2(Fo^2) + (0.102P)^2 + 1.1876P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.020
5779 reflections	Δρmax = 0.80 e Å^−3
354 parameters	Δρmin = −0.62 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
C26	1.1488 (15)	0.0610 (10)	0.5799 (5)	0.167 (5)
H26A	1.1627	0.0852	0.6480	0.200*
H26B	1.1089	−0.0217	0.5919	0.200*
C27	1.2612 (19)	0.0600 (15)	0.5222 (13)	0.280 (11)
H27A	1.3143	−0.0265	0.5399	0.336*
H27B	1.3203	0.1190	0.5447	0.336*
C28	0.7352 (10)	−0.0876 (5)	0.5820 (6)	0.131 (3)
H28A	0.6686	−0.1522	0.6090	0.158*
H28B	0.7024	−0.0103	0.6130	0.158*
C29	0.8915 (12)	−0.1398 (10)	0.6089 (6)	0.187 (5)
H29A	0.8972	−0.2190	0.6617	0.224*
H29B	0.9439	−0.0760	0.6313	0.224*
O8	1.0552 (10)	0.1655 (6)	0.5099 (6)	0.197 (3)
H4O	0.102 (4)	0.477 (3)	0.575 (3)	0.044 (9)*
H2O	0.099 (4)	0.539 (3)	0.252 (3)	0.051 (10)*
H6O	0.781 (4)	0.146 (3)	0.874 (3)	0.044 (9)*
H1O	0.664 (4)	0.275 (3)	0.091 (3)	0.048 (10)*
H5O	0.493 (4)	0.298 (3)	0.945 (3)	0.045 (9)*
C1	0.4548 (2)	0.3729 (2)	0.33454 (16)	0.0150 (4)
C2	0.5478 (2)	0.3347 (2)	0.25425 (17)	0.0184 (5)
H2	0.6414	0.2905	0.2677	0.022*
C3	0.4996 (2)	0.3634 (2)	0.15333 (17)	0.0173 (4)
C4	0.3623 (2)	0.4298 (2)	0.13218 (17)	0.0178 (4)
H4	0.3325	0.4497	0.0623	0.021*
C5	0.2716 (2)	0.4659 (2)	0.21306 (17)	0.0163 (4)
C6	0.3159 (2)	0.4365 (2)	0.31765 (16)	0.0154 (4)
C7	0.2236 (2)	0.4682 (2)	0.40435 (17)	0.0173 (4)
C8	0.2809 (2)	0.4320 (2)	0.50682 (17)	0.0187 (5)
C9	0.4180 (2)	0.3708 (2)	0.51889 (16)	0.0160 (4)
C10	0.4927 (2)	0.3254 (2)	0.61601 (17)	0.0159 (4)
C11	0.4273 (2)	0.3451 (2)	0.71410 (17)	0.0160 (4)
H11	0.3325	0.3896	0.7183	0.019*
C12	0.4996 (2)	0.3005 (2)	0.80463 (17)	0.0165 (4)
C13	0.6401 (2)	0.2345 (2)	0.79958 (17)	0.0173 (4)
C14	0.7055 (2)	0.2169 (2)	0.70281 (18)	0.0213 (5)
H14	0.8011	0.1738	0.6986	0.026*
C15	0.6331 (2)	0.2613 (2)	0.61195 (17)	0.0197 (5)
H15	0.6794	0.2481	0.5461	0.024*
C16	0.9308 (3)	−0.1003 (2)	0.88717 (19)	0.0231 (5)
C17	1.0513 (3)	−0.1935 (2)	0.89471 (18)	0.0223 (5)
C18	1.2037 (2)	−0.0349 (2)	0.85578 (19)	0.0222 (5)
C19	1.0832 (2)	0.0582 (2)	0.85053 (18)	0.0209 (5)
C20	1.3561 (3)	−0.0024 (3)	0.8373 (3)	0.0379 (7)
H20A	1.4238	−0.0809	0.8448	0.057*
H20B	1.3749	0.0490	0.8887	0.057*
H20C	1.3694	0.0462	0.7663	0.057*
C22	1.0954 (3)	0.1977 (2)	0.8230 (2)	0.0323 (6)
H22A	0.9982	0.2454	0.8236	0.048*
H22B	1.1438	0.2165	0.7529	0.048*
H22C	1.1521	0.2226	0.8744	0.048*
C23	0.7780 (3)	−0.1338 (3)	0.8993 (3)	0.0377 (7)
H23A	0.7099	−0.0555	0.8915	0.057*
H23B	0.7608	−0.1846	0.9690	0.057*
H23C	0.7636	−0.1832	0.8454	0.057*
C24	1.0390 (3)	−0.3334 (3)	0.9196 (3)	0.0375 (7)
H24A	1.1363	−0.3811	0.9209	0.056*
H24B	0.9855	−0.3572	0.8658	0.056*
H24C	0.9873	−0.3536	0.9883	0.056*
N1	0.9486 (2)	0.02339 (19)	0.86718 (15)	0.0214 (4)
N2	1.1856 (2)	−0.15823 (18)	0.87904 (15)	0.0208 (4)
O1	0.58152 (18)	0.32790 (17)	0.07046 (12)	0.0230 (4)
O2	0.13815 (18)	0.52870 (16)	0.19359 (14)	0.0227 (4)
O3	0.09570 (17)	0.52380 (17)	0.39523 (13)	0.0243 (4)
O4	0.19412 (19)	0.46146 (19)	0.58985 (13)	0.0296 (4)
O5	0.43028 (18)	0.31907 (17)	0.89816 (13)	0.0237 (4)
O6	0.70256 (19)	0.19225 (17)	0.89220 (12)	0.0235 (4)
O7	0.50375 (16)	0.34319 (15)	0.43279 (11)	0.0174 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C26	0.316 (15)	0.141 (7)	0.066 (4)	−0.122 (9)	−0.022 (6)	−0.003 (4)
C27	0.36 (2)	0.286 (18)	0.258 (17)	−0.255 (19)	0.132 (17)	−0.135 (14)
C28	0.209 (9)	0.060 (3)	0.135 (6)	−0.076 (4)	0.087 (6)	−0.047 (4)
C29	0.211 (10)	0.227 (10)	0.114 (6)	−0.147 (9)	0.015 (6)	0.066 (6)
O8	0.282 (9)	0.145 (5)	0.181 (7)	−0.109 (6)	0.103 (7)	−0.063 (5)
C1	0.0160 (10)	0.0163 (10)	0.0126 (10)	−0.0010 (8)	−0.0043 (8)	−0.0014 (8)
C2	0.0163 (10)	0.0206 (11)	0.0167 (11)	0.0035 (8)	−0.0029 (8)	−0.0024 (8)
C3	0.0205 (11)	0.0168 (10)	0.0144 (10)	0.0015 (8)	−0.0003 (8)	−0.0048 (8)
C4	0.0214 (11)	0.0177 (11)	0.0141 (10)	0.0009 (8)	−0.0061 (8)	−0.0024 (8)
C5	0.0157 (10)	0.0160 (10)	0.0168 (10)	−0.0007 (8)	−0.0048 (8)	−0.0009 (8)
C6	0.0147 (10)	0.0176 (10)	0.0144 (10)	−0.0017 (8)	−0.0019 (8)	−0.0036 (8)
C7	0.0134 (10)	0.0200 (11)	0.0174 (11)	−0.0004 (8)	−0.0014 (8)	−0.0015 (8)
C8	0.0130 (10)	0.0270 (12)	0.0150 (10)	−0.0003 (8)	0.0006 (8)	−0.0030 (8)
C9	0.0141 (10)	0.0209 (11)	0.0130 (10)	−0.0017 (8)	0.0001 (8)	−0.0038 (8)
C10	0.0157 (10)	0.0169 (10)	0.0146 (10)	−0.0013 (8)	−0.0026 (8)	−0.0013 (8)
C11	0.0132 (10)	0.0188 (10)	0.0159 (10)	−0.0011 (8)	−0.0016 (8)	−0.0032 (8)
C12	0.0161 (10)	0.0201 (11)	0.0137 (10)	−0.0026 (8)	−0.0003 (8)	−0.0037 (8)
C13	0.0188 (11)	0.0176 (11)	0.0149 (10)	−0.0002 (8)	−0.0046 (8)	−0.0009 (8)
C14	0.0164 (11)	0.0279 (12)	0.0179 (11)	0.0060 (9)	−0.0036 (9)	−0.0046 (9)
C15	0.0184 (11)	0.0265 (12)	0.0132 (10)	0.0017 (9)	0.0011 (8)	−0.0055 (8)
C16	0.0195 (11)	0.0284 (13)	0.0216 (11)	−0.0024 (9)	−0.0047 (9)	−0.0034 (9)
C17	0.0243 (12)	0.0223 (12)	0.0213 (11)	−0.0019 (9)	−0.0040 (9)	−0.0058 (9)
C18	0.0189 (11)	0.0229 (12)	0.0238 (12)	0.0014 (9)	−0.0014 (9)	−0.0042 (9)
C19	0.0194 (11)	0.0218 (11)	0.0199 (11)	0.0006 (9)	−0.0015 (9)	−0.0015 (9)
C20	0.0207 (13)	0.0309 (15)	0.061 (2)	−0.0012 (10)	0.0031 (13)	−0.0076 (13)
C22	0.0274 (13)	0.0209 (13)	0.0461 (16)	−0.0008 (10)	−0.0030 (12)	−0.0006 (11)
C23	0.0231 (13)	0.0376 (16)	0.0520 (18)	−0.0057 (11)	−0.0040 (12)	−0.0043 (13)
C24	0.0372 (15)	0.0228 (13)	0.0529 (18)	−0.0044 (11)	−0.0066 (13)	−0.0055 (12)
N1	0.0185 (9)	0.0250 (10)	0.0193 (10)	0.0018 (8)	−0.0048 (8)	−0.0018 (8)
N2	0.0200 (10)	0.0216 (10)	0.0205 (10)	0.0024 (7)	−0.0030 (8)	−0.0053 (7)
O1	0.0227 (8)	0.0309 (9)	0.0130 (8)	0.0106 (7)	−0.0029 (6)	−0.0071 (6)
O2	0.0161 (8)	0.0315 (9)	0.0184 (8)	0.0064 (7)	−0.0048 (7)	−0.0043 (7)
O3	0.0121 (8)	0.0392 (10)	0.0189 (8)	0.0044 (7)	−0.0014 (6)	−0.0027 (7)
O4	0.0141 (8)	0.0568 (12)	0.0153 (8)	0.0084 (8)	−0.0015 (6)	−0.0080 (8)
O5	0.0189 (8)	0.0393 (10)	0.0123 (8)	0.0020 (7)	−0.0010 (6)	−0.0067 (7)
O6	0.0215 (9)	0.0328 (10)	0.0139 (8)	0.0090 (7)	−0.0058 (7)	−0.0045 (7)
O7	0.0145 (7)	0.0257 (8)	0.0109 (7)	0.0027 (6)	−0.0020 (6)	−0.0036 (6)

Geometric parameters (Å, º)

C26—C27	1.235 (16)	C11—H11	0.9500
C26—O8	1.533 (12)	C12—O5	1.362 (3)
C26—H26A	0.9900	C12—C13	1.406 (3)
C26—H26B	0.9900	C13—O6	1.357 (3)
C27—C28^i	1.331 (17)	C13—C14	1.384 (3)
C27—H27A	0.9900	C14—C15	1.386 (3)
C27—H27B	0.9900	C14—H14	0.9500
C28—C27^i	1.331 (17)	C15—H15	0.9500
C28—C29	1.535 (12)	C16—N1	1.338 (3)
C28—H28A	0.9900	C16—C17	1.400 (3)
C28—H28B	0.9900	C16—C23	1.504 (3)
C29—O8^i	1.641 (12)	C17—N2	1.344 (3)
C29—H29A	0.9900	C17—C24	1.498 (3)
C29—H29B	0.9900	C18—N2	1.336 (3)
O8—C29^i	1.641 (12)	C18—C19	1.399 (3)
C1—O7	1.360 (2)	C18—C20	1.497 (3)
C1—C2	1.384 (3)	C19—N1	1.345 (3)
C1—C6	1.396 (3)	C19—C22	1.494 (3)
C2—C3	1.389 (3)	C20—H20A	0.9800
C2—H2	0.9500	C20—H20B	0.9800
C3—O1	1.349 (3)	C20—H20C	0.9800
C3—C4	1.403 (3)	C22—H22A	0.9800
C4—C5	1.371 (3)	C22—H22B	0.9800
C4—H4	0.9500	C22—H22C	0.9800
C5—O2	1.354 (3)	C23—H23A	0.9800
C5—C6	1.421 (3)	C23—H23B	0.9800
C6—C7	1.422 (3)	C23—H23C	0.9800
C7—O3	1.265 (3)	C24—H24A	0.9800
C7—C8	1.444 (3)	C24—H24B	0.9800
C8—O4	1.351 (3)	C24—H24C	0.9800
C8—C9	1.364 (3)	O1—H1O	0.93 (4)
C9—O7	1.373 (2)	O2—H2O	0.83 (4)
C9—C10	1.465 (3)	O4—H4O	0.88 (4)
C10—C15	1.397 (3)	O5—H5O	0.86 (4)
C10—C11	1.404 (3)	O6—H6O	0.87 (4)
C11—C12	1.381 (3)
C27—C26—O8	98.1 (11)	C10—C11—H11	119.7
C27—C26—H26A	112.2	O5—C12—C11	118.50 (19)
O8—C26—H26A	112.1	O5—C12—C13	121.24 (19)
C27—C26—H26B	112.2	C11—C12—C13	120.2 (2)
O8—C26—H26B	112.2	O6—C13—C14	124.3 (2)
H26A—C26—H26B	109.8	O6—C13—C12	116.52 (19)
C26—C27—C28^i	124.3 (18)	C14—C13—C12	119.16 (19)
C26—C27—H27A	106.2	C13—C14—C15	120.7 (2)
C28^i—C27—H27A	106.2	C13—C14—H14	119.7
C26—C27—H27B	106.2	C15—C14—H14	119.7
C28^i—C27—H27B	106.2	C14—C15—C10	120.8 (2)
H27A—C27—H27B	106.4	C14—C15—H15	119.6
C27^i—C28—C29	105.4 (9)	C10—C15—H15	119.6
C27^i—C28—H28A	110.7	N1—C16—C17	120.4 (2)
C29—C28—H28A	110.7	N1—C16—C23	117.4 (2)
C27^i—C28—H28B	110.7	C17—C16—C23	122.2 (2)
C29—C28—H28B	110.7	N2—C17—C16	119.7 (2)
H28A—C28—H28B	108.8	N2—C17—C24	117.2 (2)
C28—C29—O8^i	94.9 (7)	C16—C17—C24	123.1 (2)
C28—C29—H29A	112.8	N2—C18—C19	120.2 (2)
O8^i—C29—H29A	112.8	N2—C18—C20	117.3 (2)
C28—C29—H29B	112.8	C19—C18—C20	122.5 (2)
O8^i—C29—H29B	112.8	N1—C19—C18	119.9 (2)
H29A—C29—H29B	110.2	N1—C19—C22	117.0 (2)
C26—O8—C29^i	103.1 (7)	C18—C19—C22	123.0 (2)
O7—C1—C2	116.73 (18)	C18—C20—H20A	109.5
O7—C1—C6	120.69 (19)	C18—C20—H20B	109.5
C2—C1—C6	122.57 (19)	H20A—C20—H20B	109.5
C1—C2—C3	117.67 (19)	C18—C20—H20C	109.5
C1—C2—H2	121.2	H20A—C20—H20C	109.5
C3—C2—H2	121.2	H20B—C20—H20C	109.5
O1—C3—C2	121.87 (19)	C19—C22—H22A	109.5
O1—C3—C4	116.33 (19)	C19—C22—H22B	109.5
C2—C3—C4	121.8 (2)	H22A—C22—H22B	109.5
C5—C4—C3	119.53 (19)	C19—C22—H22C	109.5
C5—C4—H4	120.2	H22A—C22—H22C	109.5
C3—C4—H4	120.2	H22B—C22—H22C	109.5
O2—C5—C4	119.96 (19)	C16—C23—H23A	109.5
O2—C5—C6	119.65 (19)	C16—C23—H23B	109.5
C4—C5—C6	120.38 (19)	H23A—C23—H23B	109.5
C1—C6—C5	118.02 (19)	C16—C23—H23C	109.5
C1—C6—C7	119.68 (19)	H23A—C23—H23C	109.5
C5—C6—C7	122.29 (19)	H23B—C23—H23C	109.5
O3—C7—C6	123.2 (2)	C17—C24—H24A	109.5
O3—C7—C8	119.9 (2)	C17—C24—H24B	109.5
C6—C7—C8	116.94 (19)	H24A—C24—H24B	109.5
O4—C8—C9	121.5 (2)	C17—C24—H24C	109.5
O4—C8—C7	117.49 (19)	H24A—C24—H24C	109.5
C9—C8—C7	121.0 (2)	H24B—C24—H24C	109.5
C8—C9—O7	120.00 (19)	C16—N1—C19	119.7 (2)
C8—C9—C10	128.5 (2)	C18—N2—C17	120.1 (2)
O7—C9—C10	111.49 (17)	C3—O1—H1O	112 (2)
C15—C10—C11	118.48 (19)	C5—O2—H2O	106 (3)
C15—C10—C9	119.73 (19)	C8—O4—H4O	112 (2)
C11—C10—C9	121.78 (19)	C12—O5—H5O	107 (2)
C12—C11—C10	120.68 (19)	C13—O6—H6O	103 (2)
C12—C11—H11	119.7	C1—O7—C9	121.65 (16)

Symmetry code: (i) −x+2, −y, −z+1.

(QBP_I)

Crystal data

C29H26N2O9	V = 1268.29 (17) Å^3
Mr = 546.52	Z = 2
Triclinic, P1	F(000) = 572
a = 9.8334 (7) Å	Dx = 1.431 Mg m^−3
b = 10.7098 (8) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.0790 (9) Å	µ = 0.11 mm^−1
α = 102.815 (7)°	T = 150 K
β = 95.031 (7)°	Prism, yellow
γ = 106.846 (7)°	1.00 × 0.50 × 0.20 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.016
Tmin = 0.898, Tmax = 1.000	θmax = 27.5°, θmin = 3.1°
13454 measured reflections	h = −12→12
5791 independent reflections	k = −13→13
5160 reflections with I > 2σ(I)	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0579P)^2 + 0.5172P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
5791 reflections	Δρmax = 0.34 e Å^−3
381 parameters	Δρmin = −0.23 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
H6O	−0.145 (2)	0.808 (2)	0.3830 (17)	0.050 (6)*
H1O	−0.059 (2)	0.706 (2)	−0.4034 (16)	0.046 (5)*
H2O	0.417 (2)	0.502 (2)	−0.2448 (18)	0.048 (6)*
H5O	0.076 (2)	0.6585 (18)	0.4404 (15)	0.037 (5)*
H4O	0.418 (2)	0.536 (2)	0.0677 (16)	0.049 (6)*
O4	0.34381 (10)	0.56223 (10)	0.08956 (7)	0.0196 (2)
O5	0.09286 (9)	0.66914 (8)	−0.06248 (6)	0.01333 (17)
O7	−0.07250 (9)	0.77159 (9)	0.39368 (7)	0.01733 (19)
O3	0.41733 (9)	0.50858 (9)	−0.10629 (7)	0.01772 (19)
O1	0.01337 (9)	0.66939 (9)	−0.42443 (6)	0.01673 (19)
O2	0.38140 (10)	0.51086 (9)	−0.30610 (7)	0.0192 (2)
O6	0.13133 (9)	0.64637 (9)	0.39238 (7)	0.01538 (18)
C7	0.31720 (12)	0.55992 (11)	−0.09447 (9)	0.0132 (2)
C9	0.16145 (12)	0.64101 (11)	0.02148 (9)	0.0120 (2)
C2	0.05183 (12)	0.67459 (11)	−0.23981 (9)	0.0133 (2)
H2	−0.0218	0.7137	−0.2248	0.016*
C10	0.09942 (12)	0.67357 (11)	0.11798 (9)	0.0122 (2)
C14	−0.06751 (12)	0.76883 (12)	0.20777 (9)	0.0147 (2)
H14	−0.1400	0.8110	0.2059	0.018*
C6	0.24165 (12)	0.58954 (11)	−0.17970 (9)	0.0126 (2)
C1	0.13030 (12)	0.64403 (11)	−0.16097 (9)	0.0121 (2)
C11	0.14277 (12)	0.64187 (11)	0.21200 (9)	0.0122 (2)
H11	0.2131	0.5971	0.2135	0.015*
C4	0.19565 (13)	0.59002 (12)	−0.36474 (9)	0.0149 (2)
H4	0.2160	0.5709	−0.4351	0.018*
C8	0.27235 (12)	0.58924 (12)	0.00789 (9)	0.0136 (2)
C12	0.08344 (12)	0.67561 (11)	0.30213 (9)	0.0123 (2)
C3	0.08526 (12)	0.64575 (11)	−0.34182 (9)	0.0132 (2)
C5	0.27391 (12)	0.56343 (11)	−0.28457 (9)	0.0136 (2)
C15	−0.00755 (12)	0.73640 (12)	0.11731 (9)	0.0143 (2)
H15	−0.0393	0.7570	0.0542	0.017*
C13	−0.02239 (12)	0.74008 (11)	0.30118 (9)	0.0132 (2)
N1	0.19762 (12)	0.22733 (11)	0.38214 (8)	0.0197 (2)
N2	0.72501 (12)	−0.10917 (11)	0.37290 (9)	0.0211 (2)
C21	0.51872 (13)	0.02605 (12)	0.37025 (10)	0.0162 (2)
C18	0.40857 (13)	0.09659 (12)	0.37189 (9)	0.0158 (2)
C22	0.65845 (13)	0.09109 (12)	0.42469 (10)	0.0182 (2)
H22	0.6864	0.1836	0.4625	0.022*
C23	0.75710 (13)	0.02094 (13)	0.42389 (10)	0.0188 (2)
H23	0.8520	0.0678	0.4614	0.023*
C20	0.16759 (14)	0.09933 (14)	0.32669 (11)	0.0237 (3)
H20	0.0722	0.0524	0.2902	0.028*
C19	0.26792 (14)	0.03112 (13)	0.31947 (11)	0.0218 (3)
H19	0.2407	−0.0601	0.2788	0.026*
C25	0.48646 (15)	−0.10901 (14)	0.31565 (13)	0.0297 (3)
H25	0.3931	−0.1580	0.2761	0.036*
C17	0.43971 (15)	0.23047 (15)	0.42872 (14)	0.0330 (4)
H17	0.5345	0.2806	0.4652	0.040*
C16	0.33234 (16)	0.29065 (15)	0.43203 (13)	0.0325 (3)
H16	0.3562	0.3819	0.4720	0.039*
C24	0.59124 (16)	−0.17161 (15)	0.31927 (13)	0.0318 (3)
H24	0.5668	−0.2639	0.2816	0.038*
O9	0.82828 (11)	0.97350 (11)	0.06621 (9)	0.0312 (2)
O8	0.54964 (11)	0.84048 (11)	−0.05471 (9)	0.0337 (3)
C26	0.70432 (16)	1.00025 (15)	0.10238 (13)	0.0314 (3)
H26A	0.6906	1.0783	0.0792	0.038*
H26B	0.7190	1.0237	0.1810	0.038*
C28	0.67319 (17)	0.81241 (15)	−0.09036 (13)	0.0329 (3)
H28A	0.6587	0.7878	−0.1690	0.039*
H28B	0.6868	0.7350	−0.0661	0.039*
C27	0.57145 (16)	0.87812 (16)	0.05860 (13)	0.0338 (3)
H27A	0.5826	0.8017	0.0856	0.041*
H27B	0.4863	0.8991	0.0832	0.041*
C29	0.80567 (17)	0.93506 (16)	−0.04703 (13)	0.0332 (3)
H29A	0.8909	0.9144	−0.0718	0.040*
H29B	0.7938	1.0111	−0.0743	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0194 (4)	0.0352 (5)	0.0138 (4)	0.0195 (4)	0.0044 (3)	0.0105 (4)
O5	0.0149 (4)	0.0184 (4)	0.0102 (4)	0.0102 (3)	0.0023 (3)	0.0042 (3)
O7	0.0186 (4)	0.0258 (5)	0.0134 (4)	0.0143 (4)	0.0059 (3)	0.0057 (3)
O3	0.0173 (4)	0.0263 (5)	0.0158 (4)	0.0149 (4)	0.0038 (3)	0.0069 (3)
O1	0.0190 (4)	0.0257 (5)	0.0122 (4)	0.0149 (4)	0.0037 (3)	0.0076 (3)
O2	0.0207 (4)	0.0302 (5)	0.0146 (4)	0.0185 (4)	0.0052 (3)	0.0065 (4)
O6	0.0173 (4)	0.0218 (4)	0.0108 (4)	0.0101 (3)	0.0033 (3)	0.0061 (3)
C7	0.0120 (5)	0.0144 (5)	0.0143 (5)	0.0054 (4)	0.0018 (4)	0.0041 (4)
C9	0.0120 (5)	0.0141 (5)	0.0104 (5)	0.0047 (4)	0.0001 (4)	0.0039 (4)
C2	0.0130 (5)	0.0152 (5)	0.0138 (5)	0.0080 (4)	0.0029 (4)	0.0035 (4)
C10	0.0114 (5)	0.0129 (5)	0.0125 (5)	0.0047 (4)	0.0017 (4)	0.0028 (4)
C14	0.0136 (5)	0.0174 (5)	0.0154 (5)	0.0085 (4)	0.0019 (4)	0.0041 (4)
C6	0.0124 (5)	0.0133 (5)	0.0127 (5)	0.0052 (4)	0.0015 (4)	0.0034 (4)
C1	0.0134 (5)	0.0118 (5)	0.0110 (5)	0.0045 (4)	0.0025 (4)	0.0023 (4)
C11	0.0111 (5)	0.0124 (5)	0.0134 (5)	0.0046 (4)	0.0013 (4)	0.0031 (4)
C4	0.0162 (6)	0.0185 (6)	0.0122 (5)	0.0080 (5)	0.0045 (4)	0.0041 (4)
C8	0.0131 (5)	0.0170 (5)	0.0121 (5)	0.0065 (4)	0.0005 (4)	0.0048 (4)
C12	0.0119 (5)	0.0129 (5)	0.0119 (5)	0.0036 (4)	0.0006 (4)	0.0038 (4)
C3	0.0144 (5)	0.0141 (5)	0.0121 (5)	0.0056 (4)	0.0007 (4)	0.0049 (4)
C5	0.0136 (5)	0.0141 (5)	0.0148 (5)	0.0071 (4)	0.0035 (4)	0.0032 (4)
C15	0.0144 (5)	0.0171 (5)	0.0131 (5)	0.0069 (4)	0.0012 (4)	0.0052 (4)
C13	0.0122 (5)	0.0143 (5)	0.0127 (5)	0.0043 (4)	0.0029 (4)	0.0023 (4)
N1	0.0202 (5)	0.0244 (5)	0.0198 (5)	0.0131 (4)	0.0054 (4)	0.0075 (4)
N2	0.0184 (5)	0.0247 (6)	0.0238 (5)	0.0126 (4)	0.0059 (4)	0.0051 (4)
C21	0.0144 (5)	0.0178 (6)	0.0185 (6)	0.0071 (4)	0.0053 (4)	0.0054 (5)
C18	0.0151 (5)	0.0173 (6)	0.0177 (6)	0.0073 (4)	0.0057 (4)	0.0064 (4)
C22	0.0181 (6)	0.0173 (6)	0.0193 (6)	0.0066 (5)	0.0011 (5)	0.0041 (5)
C23	0.0157 (6)	0.0235 (6)	0.0185 (6)	0.0075 (5)	0.0020 (5)	0.0066 (5)
C20	0.0176 (6)	0.0229 (6)	0.0305 (7)	0.0091 (5)	−0.0023 (5)	0.0055 (5)
C19	0.0195 (6)	0.0169 (6)	0.0280 (7)	0.0082 (5)	−0.0013 (5)	0.0030 (5)
C25	0.0156 (6)	0.0206 (7)	0.0453 (9)	0.0072 (5)	−0.0029 (6)	−0.0058 (6)
C17	0.0161 (6)	0.0235 (7)	0.0509 (9)	0.0086 (5)	−0.0019 (6)	−0.0075 (6)
C16	0.0237 (7)	0.0226 (7)	0.0462 (9)	0.0129 (6)	0.0009 (6)	−0.0066 (6)
C24	0.0221 (7)	0.0211 (7)	0.0476 (9)	0.0118 (5)	−0.0004 (6)	−0.0047 (6)
O9	0.0219 (5)	0.0345 (6)	0.0339 (6)	0.0060 (4)	−0.0031 (4)	0.0091 (4)
O8	0.0232 (5)	0.0297 (5)	0.0406 (6)	0.0044 (4)	−0.0057 (4)	0.0034 (5)
C26	0.0250 (7)	0.0268 (7)	0.0372 (8)	0.0046 (6)	−0.0014 (6)	0.0050 (6)
C28	0.0301 (8)	0.0281 (7)	0.0367 (8)	0.0064 (6)	0.0013 (6)	0.0063 (6)
C27	0.0248 (7)	0.0299 (8)	0.0399 (9)	0.0022 (6)	0.0024 (6)	0.0050 (6)
C29	0.0267 (7)	0.0347 (8)	0.0349 (8)	0.0043 (6)	0.0014 (6)	0.0114 (6)

Geometric parameters (Å, º)

O4—C8	1.3571 (14)	N1—C20	1.3339 (17)
O4—H4O	0.90 (2)	N2—C23	1.3349 (17)
O5—C1	1.3617 (13)	N2—C24	1.3378 (18)
O5—C9	1.3734 (13)	C21—C22	1.3906 (17)
O7—C13	1.3565 (14)	C21—C25	1.3925 (18)
O7—H6O	0.92 (2)	C21—C18	1.4885 (16)
O3—C7	1.2644 (14)	C18—C19	1.3903 (17)
O1—C3	1.3499 (13)	C18—C17	1.3910 (18)
O1—H1O	0.94 (2)	C22—C23	1.3879 (17)
O2—C5	1.3565 (14)	C22—H22	0.9500
O2—H2O	0.88 (2)	C23—H23	0.9500
O6—C12	1.3658 (13)	C20—C19	1.3855 (18)
O6—H5O	0.88 (2)	C20—H20	0.9500
C7—C6	1.4295 (15)	C19—H19	0.9500
C7—C8	1.4431 (16)	C25—C24	1.3854 (19)
C9—C8	1.3671 (16)	C25—H25	0.9500
C9—C10	1.4662 (15)	C17—C16	1.3864 (19)
C2—C1	1.3865 (16)	C17—H17	0.9500
C2—C3	1.3916 (16)	C16—H16	0.9500
C2—H2	0.9500	C24—H24	0.9500
C10—C15	1.4038 (15)	O9—C29	1.4252 (19)
C10—C11	1.4092 (15)	O9—C26	1.4265 (19)
C14—C15	1.3882 (16)	O8—C28	1.426 (2)
C14—C13	1.3911 (16)	O8—C27	1.426 (2)
C14—H14	0.9500	C26—C27	1.514 (2)
C6—C1	1.3977 (15)	C26—H26A	0.9900
C6—C5	1.4204 (16)	C26—H26B	0.9900
C11—C12	1.3836 (15)	C28—C29	1.514 (2)
C11—H11	0.9500	C28—H28A	0.9900
C4—C5	1.3751 (16)	C28—H28B	0.9900
C4—C3	1.4063 (16)	C27—H27A	0.9900
C4—H4	0.9500	C27—H27B	0.9900
C12—C13	1.4064 (16)	C29—H29A	0.9900
C15—H15	0.9500	C29—H29B	0.9900
N1—C16	1.3312 (18)
C8—O4—H4O	109.4 (13)	C25—C21—C18	121.72 (11)
C1—O5—C9	121.62 (9)	C19—C18—C17	116.38 (11)
C13—O7—H6O	109.3 (13)	C19—C18—C21	121.85 (11)
C3—O1—H1O	111.6 (12)	C17—C18—C21	121.74 (11)
C5—O2—H2O	104.9 (14)	C23—C22—C21	120.05 (11)
C12—O6—H5O	110.4 (12)	C23—C22—H22	120.0
O3—C7—C6	122.88 (10)	C21—C22—H22	120.0
O3—C7—C8	120.33 (10)	N2—C23—C22	123.14 (12)
C6—C7—C8	116.78 (10)	N2—C23—H23	118.4
C8—C9—O5	120.03 (10)	C22—C23—H23	118.4
C8—C9—C10	128.67 (10)	N1—C20—C19	123.58 (12)
O5—C9—C10	111.30 (9)	N1—C20—H20	118.2
C1—C2—C3	117.35 (10)	C19—C20—H20	118.2
C1—C2—H2	121.3	C20—C19—C18	119.82 (12)
C3—C2—H2	121.3	C20—C19—H19	120.1
C15—C10—C11	118.53 (10)	C18—C19—H19	120.1
C15—C10—C9	119.66 (10)	C24—C25—C21	119.65 (13)
C11—C10—C9	121.81 (10)	C24—C25—H25	120.2
C15—C14—C13	120.62 (11)	C21—C25—H25	120.2
C15—C14—H14	119.7	C16—C17—C18	119.93 (13)
C13—C14—H14	119.7	C16—C17—H17	120.0
C1—C6—C5	118.09 (10)	C18—C17—H17	120.0
C1—C6—C7	119.62 (10)	N1—C16—C17	123.47 (13)
C5—C6—C7	122.28 (10)	N1—C16—H16	118.3
O5—C1—C2	116.39 (10)	C17—C16—H16	118.3
O5—C1—C6	120.77 (10)	N2—C24—C25	123.56 (13)
C2—C1—C6	122.84 (10)	N2—C24—H24	118.2
C12—C11—C10	120.35 (10)	C25—C24—H24	118.2
C12—C11—H11	119.8	C29—O9—C26	109.72 (11)
C10—C11—H11	119.8	C28—O8—C27	109.64 (12)
C5—C4—C3	119.56 (10)	O9—C26—C27	110.61 (13)
C5—C4—H4	120.2	O9—C26—H26A	109.5
C3—C4—H4	120.2	C27—C26—H26A	109.5
O4—C8—C9	121.52 (10)	O9—C26—H26B	109.5
O4—C8—C7	117.31 (10)	C27—C26—H26B	109.5
C9—C8—C7	121.17 (10)	H26A—C26—H26B	108.1
O6—C12—C11	118.46 (10)	O8—C28—C29	110.08 (13)
O6—C12—C13	120.78 (10)	O8—C28—H28A	109.6
C11—C12—C13	120.76 (10)	C29—C28—H28A	109.6
O1—C3—C2	121.91 (10)	O8—C28—H28B	109.6
O1—C3—C4	116.21 (10)	C29—C28—H28B	109.6
C2—C3—C4	121.88 (10)	H28A—C28—H28B	108.2
O2—C5—C4	119.77 (10)	O8—C27—C26	110.62 (13)
O2—C5—C6	119.97 (10)	O8—C27—H27A	109.5
C4—C5—C6	120.26 (10)	C26—C27—H27A	109.5
C14—C15—C10	120.77 (10)	O8—C27—H27B	109.5
C14—C15—H15	119.6	C26—C27—H27B	109.5
C10—C15—H15	119.6	H27A—C27—H27B	108.1
O7—C13—C14	124.36 (10)	O9—C29—C28	110.80 (13)
O7—C13—C12	116.68 (10)	O9—C29—H29A	109.5
C14—C13—C12	118.95 (10)	C28—C29—H29A	109.5
C16—N1—C20	116.82 (11)	O9—C29—H29B	109.5
C23—N2—C24	116.98 (11)	C28—C29—H29B	109.5
C22—C21—C25	116.61 (11)	H29A—C29—H29B	108.1
C22—C21—C18	121.66 (11)

(QBP_II)

Crystal data

C29H18N2O8	V = 1271.6 (5) Å^3
Mr = 522.45	Z = 2
Triclinic, P1	F(000) = 540
a = 9.806 (2) Å	Dx = 1.365 Mg m^−3
b = 10.778 (2) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.055 (3) Å	µ = 0.10 mm^−1
α = 102.833 (7)°	T = 150 K
β = 94.525 (7)°	Plate, yellow
γ = 106.943 (7)°	0.60 × 0.30 × 0.25 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.037
Tmin = 0.741, Tmax = 1.000	θmax = 26.0°, θmin = 3.1°
10628 measured reflections	h = −12→12
4943 independent reflections	k = −13→13
3753 reflections with I > 2σ(I)	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.075	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.214	w = 1/[σ^2(Fo^2) + (0.103P)^2 + 1.8694P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
4943 reflections	Δρmax = 1.14 e Å^−3
372 parameters	Δρmin = −0.90 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
H5O	0.076 (4)	0.668 (3)	0.943 (3)	0.025 (9)*
H6O	−0.146 (5)	0.809 (4)	0.889 (3)	0.054 (13)*
H4O	0.419 (4)	0.539 (4)	0.571 (3)	0.033 (10)*
H2O	0.412 (5)	0.495 (5)	0.250 (4)	0.058 (14)*
H1O	−0.063 (5)	0.704 (4)	0.099 (4)	0.057 (13)*
O7	0.0898 (2)	0.66444 (19)	0.43931 (14)	0.0165 (4)
O4	0.3453 (2)	0.5638 (2)	0.59061 (15)	0.0233 (5)
O2	0.3758 (2)	0.5070 (2)	0.19129 (17)	0.0239 (5)
O5	0.1335 (2)	0.6521 (2)	0.89714 (15)	0.0204 (5)
O3	0.4134 (2)	0.5038 (2)	0.39225 (15)	0.0214 (5)
O1	0.0122 (2)	0.6716 (2)	0.07879 (15)	0.0219 (5)
O6	−0.0737 (2)	0.7738 (2)	0.89673 (15)	0.0231 (5)
C9	0.1602 (3)	0.6388 (3)	0.5235 (2)	0.0154 (6)
C2	0.0500 (3)	0.6736 (3)	0.2629 (2)	0.0175 (6)
H2	−0.0232	0.7130	0.2792	0.021*
C7	0.3137 (3)	0.5556 (3)	0.4050 (2)	0.0167 (6)
C6	0.2388 (3)	0.5867 (3)	0.3208 (2)	0.0163 (6)
C11	0.1447 (3)	0.6450 (3)	0.7158 (2)	0.0150 (6)
H11	0.2171	0.6028	0.7180	0.018*
C10	0.0989 (3)	0.6724 (3)	0.6207 (2)	0.0157 (6)
C1	0.1279 (3)	0.6412 (3)	0.3405 (2)	0.0161 (6)
C4	0.1926 (3)	0.5897 (3)	0.1356 (2)	0.0200 (6)
H4	0.2128	0.5712	0.0648	0.024*
C14	−0.0690 (3)	0.7652 (3)	0.7099 (2)	0.0200 (6)
H14	−0.1431	0.8055	0.7077	0.024*
C12	0.0847 (3)	0.6792 (3)	0.8061 (2)	0.0168 (6)
C3	0.0834 (3)	0.6464 (3)	0.1601 (2)	0.0179 (6)
C8	0.2713 (3)	0.5874 (3)	0.5086 (2)	0.0167 (6)
C13	−0.0222 (3)	0.7412 (3)	0.8047 (2)	0.0181 (6)
C15	−0.0104 (3)	0.7319 (3)	0.6189 (2)	0.0175 (6)
H15	−0.0442	0.7495	0.5551	0.021*
C5	0.2704 (3)	0.5609 (3)	0.2145 (2)	0.0184 (6)
N1	0.8028 (3)	0.7741 (3)	0.1238 (2)	0.0245 (6)
N2	0.2757 (3)	1.1078 (3)	0.1329 (2)	0.0291 (6)
C18	0.5909 (3)	0.9023 (3)	0.1355 (2)	0.0209 (6)
C21	0.4808 (3)	0.9723 (3)	0.1378 (2)	0.0217 (6)
C25	0.3462 (3)	0.9126 (3)	0.0753 (2)	0.0261 (7)
H25	0.3211	0.8233	0.0322	0.031*
C24	0.2486 (3)	0.9830 (3)	0.0758 (2)	0.0260 (7)
H24	0.1569	0.9392	0.0327	0.031*
C22	0.5076 (4)	1.1015 (4)	0.2018 (3)	0.0452 (10)
H22	0.5959	1.1460	0.2490	0.054*
C17	0.7283 (4)	0.9642 (4)	0.1915 (3)	0.0384 (9)
H17	0.7537	1.0529	0.2357	0.046*
C16	0.8288 (4)	0.8972 (4)	0.1833 (3)	0.0414 (9)
H16	0.9226	0.9424	0.2229	0.050*
C19	0.5635 (4)	0.7735 (4)	0.0729 (4)	0.0483 (11)
H19	0.4708	0.7258	0.0322	0.058*
C20	0.6706 (4)	0.7142 (4)	0.0694 (3)	0.0442 (10)
H20	0.6486	0.6256	0.0257	0.053*
C23	0.4034 (4)	1.1640 (4)	0.1955 (4)	0.0509 (12)
H23	0.4242	1.2527	0.2387	0.061*
C29	0.6812 (5)	0.7838 (5)	0.4219 (5)	0.0745 (17)
O8	0.8218 (4)	0.8793 (3)	0.4389 (4)	0.0797 (12)
C28	0.6085 (12)	0.8341 (11)	0.5020 (12)	0.259 (10)
C26	0.8146 (7)	1.0005 (5)	0.5100 (8)	0.115 (3)
C27	0.7097 (11)	0.9830 (10)	0.5565 (12)	0.249 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0193 (10)	0.0241 (10)	0.0112 (9)	0.0129 (8)	0.0021 (7)	0.0066 (7)
O4	0.0255 (11)	0.0405 (13)	0.0139 (10)	0.0226 (10)	0.0041 (8)	0.0105 (9)
O2	0.0254 (11)	0.0381 (12)	0.0165 (10)	0.0213 (10)	0.0055 (9)	0.0080 (9)
O5	0.0241 (11)	0.0301 (11)	0.0121 (9)	0.0140 (9)	0.0047 (8)	0.0077 (8)
O3	0.0223 (10)	0.0325 (11)	0.0160 (10)	0.0177 (9)	0.0036 (8)	0.0072 (8)
O1	0.0261 (11)	0.0346 (12)	0.0138 (10)	0.0195 (9)	0.0044 (8)	0.0104 (8)
O6	0.0247 (11)	0.0354 (12)	0.0157 (10)	0.0192 (10)	0.0061 (8)	0.0057 (9)
C9	0.0177 (13)	0.0154 (13)	0.0126 (13)	0.0045 (10)	0.0004 (10)	0.0042 (10)
C2	0.0197 (14)	0.0219 (14)	0.0153 (13)	0.0120 (11)	0.0042 (11)	0.0060 (11)
C7	0.0149 (13)	0.0175 (13)	0.0168 (13)	0.0054 (11)	0.0010 (11)	0.0031 (11)
C6	0.0175 (13)	0.0179 (13)	0.0142 (13)	0.0077 (11)	0.0013 (11)	0.0034 (10)
C11	0.0163 (13)	0.0173 (13)	0.0138 (13)	0.0081 (11)	0.0026 (10)	0.0051 (10)
C10	0.0181 (13)	0.0157 (13)	0.0134 (13)	0.0061 (11)	0.0025 (10)	0.0032 (10)
C1	0.0193 (14)	0.0174 (13)	0.0120 (13)	0.0069 (11)	0.0033 (10)	0.0029 (10)
C4	0.0240 (15)	0.0255 (15)	0.0127 (13)	0.0105 (12)	0.0039 (11)	0.0054 (11)
C14	0.0183 (14)	0.0260 (15)	0.0206 (14)	0.0137 (12)	0.0039 (11)	0.0066 (12)
C12	0.0176 (13)	0.0205 (14)	0.0124 (13)	0.0059 (11)	0.0012 (10)	0.0053 (10)
C3	0.0206 (14)	0.0215 (14)	0.0146 (13)	0.0096 (11)	0.0024 (11)	0.0068 (11)
C8	0.0180 (13)	0.0209 (14)	0.0135 (13)	0.0084 (11)	0.0005 (10)	0.0064 (10)
C13	0.0188 (14)	0.0222 (14)	0.0146 (13)	0.0083 (11)	0.0057 (11)	0.0042 (11)
C15	0.0209 (14)	0.0230 (14)	0.0120 (12)	0.0115 (11)	0.0004 (11)	0.0062 (10)
C5	0.0208 (14)	0.0214 (14)	0.0155 (13)	0.0098 (11)	0.0040 (11)	0.0053 (11)
N1	0.0285 (14)	0.0315 (14)	0.0210 (13)	0.0173 (11)	0.0057 (11)	0.0104 (11)
N2	0.0242 (14)	0.0319 (15)	0.0332 (15)	0.0162 (12)	0.0055 (11)	0.0022 (12)
C18	0.0218 (15)	0.0235 (15)	0.0201 (14)	0.0082 (12)	0.0066 (12)	0.0080 (11)
C21	0.0209 (15)	0.0243 (15)	0.0210 (14)	0.0082 (12)	0.0054 (12)	0.0059 (12)
C25	0.0273 (16)	0.0245 (15)	0.0260 (15)	0.0118 (13)	−0.0017 (13)	0.0029 (12)
C24	0.0252 (16)	0.0296 (16)	0.0239 (15)	0.0100 (13)	0.0013 (12)	0.0072 (13)
C22	0.0225 (17)	0.037 (2)	0.063 (3)	0.0142 (15)	−0.0086 (17)	−0.0145 (18)
C17	0.0341 (19)	0.0318 (18)	0.044 (2)	0.0192 (15)	−0.0134 (16)	−0.0067 (15)
C16	0.0321 (19)	0.0344 (19)	0.050 (2)	0.0163 (16)	−0.0178 (17)	−0.0038 (16)
C19	0.0211 (17)	0.037 (2)	0.071 (3)	0.0124 (15)	−0.0039 (17)	−0.0169 (19)
C20	0.0294 (19)	0.0331 (19)	0.059 (2)	0.0152 (15)	0.0010 (17)	−0.0143 (17)
C23	0.0294 (19)	0.036 (2)	0.074 (3)	0.0177 (16)	−0.0067 (19)	−0.0181 (19)
C29	0.044 (3)	0.046 (3)	0.121 (5)	−0.005 (2)	−0.017 (3)	0.032 (3)
O8	0.052 (2)	0.0438 (18)	0.129 (3)	−0.0028 (15)	−0.006 (2)	0.026 (2)
C28	0.132 (8)	0.135 (8)	0.332 (17)	−0.097 (7)	0.121 (10)	−0.139 (10)
C26	0.060 (4)	0.029 (3)	0.228 (9)	−0.002 (2)	0.011 (5)	0.003 (4)
C27	0.115 (7)	0.117 (7)	0.357 (18)	−0.084 (6)	0.123 (10)	−0.123 (9)

Geometric parameters (Å, º)

O7—C1	1.362 (3)	C14—C13	1.389 (4)
O7—C9	1.373 (3)	C14—H14	0.9500
O4—C8	1.358 (3)	C12—C13	1.399 (4)
O4—H4O	0.88 (4)	C15—H15	0.9500
O2—C5	1.349 (3)	N1—C16	1.320 (4)
O2—H2O	0.87 (5)	N1—C20	1.328 (4)
O5—C12	1.369 (3)	N2—C24	1.323 (4)
O5—H5O	0.88 (4)	N2—C23	1.334 (5)
O3—C7	1.264 (3)	C18—C17	1.378 (5)
O1—C3	1.345 (3)	C18—C19	1.383 (5)
O1—H1O	0.93 (5)	C18—C21	1.485 (4)
O6—C13	1.355 (3)	C21—C25	1.387 (4)
O6—H6O	0.90 (5)	C21—C22	1.393 (5)
C9—C8	1.367 (4)	C25—C24	1.383 (4)
C9—C10	1.466 (4)	C25—H25	0.9500
C2—C1	1.386 (4)	C24—H24	0.9500
C2—C3	1.395 (4)	C22—C23	1.384 (5)
C2—H2	0.9500	C22—H22	0.9500
C7—C6	1.428 (4)	C17—C16	1.380 (5)
C7—C8	1.444 (4)	C17—H17	0.9500
C6—C1	1.395 (4)	C16—H16	0.9500
C6—C5	1.430 (4)	C19—C20	1.378 (5)
C11—C12	1.383 (4)	C19—H19	0.9500
C11—C10	1.408 (4)	C20—H20	0.9500
C11—H11	0.9500	C23—H23	0.9500
C10—C15	1.402 (4)	C29—C28	1.409 (11)
C4—C5	1.375 (4)	C29—O8	1.426 (5)
C4—C3	1.404 (4)	O8—C26	1.449 (8)
C4—H4	0.9500	C28—C27	1.587 (9)
C14—C15	1.382 (4)	C26—C27	1.224 (11)
C1—O7—C9	122.0 (2)	C14—C13—C12	118.5 (2)
C8—O4—H4O	111 (2)	C14—C15—C10	120.0 (2)
C5—O2—H2O	107 (3)	C14—C15—H15	120.0
C12—O5—H5O	107 (2)	C10—C15—H15	120.0
C3—O1—H1O	112 (3)	O2—C5—C4	119.9 (2)
C13—O6—H6O	113 (3)	O2—C5—C6	119.8 (2)
C8—C9—O7	119.7 (2)	C4—C5—C6	120.2 (3)
C8—C9—C10	129.0 (2)	C16—N1—C20	116.2 (3)
O7—C9—C10	111.3 (2)	C24—N2—C23	116.4 (3)
C1—C2—C3	117.4 (2)	C17—C18—C19	116.2 (3)
C1—C2—H2	121.3	C17—C18—C21	121.9 (3)
C3—C2—H2	121.3	C19—C18—C21	121.8 (3)
O3—C7—C6	123.1 (2)	C25—C21—C22	116.6 (3)
O3—C7—C8	120.2 (2)	C25—C21—C18	121.5 (3)
C6—C7—C8	116.7 (2)	C22—C21—C18	121.9 (3)
C1—C6—C7	119.8 (2)	C24—C25—C21	120.0 (3)
C1—C6—C5	117.7 (2)	C24—C25—H25	120.0
C7—C6—C5	122.5 (2)	C21—C25—H25	120.0
C12—C11—C10	120.3 (2)	N2—C24—C25	123.7 (3)
C12—C11—H11	119.8	N2—C24—H24	118.1
C10—C11—H11	119.8	C25—C24—H24	118.1
C15—C10—C11	118.7 (2)	C23—C22—C21	118.9 (3)
C15—C10—C9	119.1 (2)	C23—C22—H22	120.5
C11—C10—C9	122.2 (2)	C21—C22—H22	120.5
O7—C1—C2	116.3 (2)	C18—C17—C16	119.9 (3)
O7—C1—C6	120.5 (2)	C18—C17—H17	120.0
C2—C1—C6	123.2 (2)	C16—C17—H17	120.0
C5—C4—C3	119.8 (2)	N1—C16—C17	124.0 (3)
C5—C4—H4	120.1	N1—C16—H16	118.0
C3—C4—H4	120.1	C17—C16—H16	118.0
C15—C14—C13	121.5 (3)	C20—C19—C18	120.0 (3)
C15—C14—H14	119.2	C20—C19—H19	120.0
C13—C14—H14	119.2	C18—C19—H19	120.0
O5—C12—C11	118.4 (2)	N1—C20—C19	123.7 (3)
O5—C12—C13	120.8 (2)	N1—C20—H20	118.2
C11—C12—C13	120.8 (2)	C19—C20—H20	118.2
O1—C3—C2	122.1 (2)	N2—C23—C22	124.3 (3)
O1—C3—C4	116.3 (2)	N2—C23—H23	117.8
C2—C3—C4	121.7 (2)	C22—C23—H23	117.8
O4—C8—C9	121.2 (2)	C28—C29—O8	106.3 (5)
O4—C8—C7	117.6 (2)	C29—O8—C26	106.1 (5)
C9—C8—C7	121.2 (2)	C29—C28—C27	105.1 (7)
O6—C13—C14	124.1 (3)	C27—C26—O8	113.9 (6)
O6—C13—C12	117.4 (2)	C26—C27—C28	106.0 (8)

(QBP_III)

Crystal data

C30H22N3O7	V = 1277.0 (11) Å^3
Mr = 536.50	Z = 2
Triclinic, P1	F(000) = 558
a = 9.844 (5) Å	Dx = 1.395 Mg m^−3
b = 10.636 (6) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.071 (7) Å	µ = 0.10 mm^−1
α = 98.324 (7)°	T = 150 K
β = 94.601 (7)°	Plate, yellow
γ = 107.947 (8)°	0.65 × 0.45 × 0.30 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.022
Tmin = 0.857, Tmax = 1.000	θmax = 27.4°, θmin = 3.2°
13246 measured reflections	h = −12→12
5767 independent reflections	k = −13→13
4834 reflections with I > 2σ(I)	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0543P)^2 + 0.4614P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
5767 reflections	Δρmax = 0.34 e Å^−3
381 parameters	Δρmin = −0.21 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	−0.80415 (13)	1.22475 (13)	0.89128 (9)	0.0267 (3)
N2	−0.26719 (13)	0.90374 (13)	0.84950 (10)	0.0283 (3)
H1O	−0.060 (2)	0.704 (2)	0.0858 (15)	0.048 (5)*
H2O	0.400 (2)	0.481 (2)	0.2524 (17)	0.052 (6)*
H5O	0.087 (2)	0.671 (2)	0.9361 (16)	0.046 (6)*
H6O	−0.134 (2)	0.821 (2)	0.8669 (16)	0.052 (6)*
H4O	0.416 (2)	0.535 (2)	0.5702 (17)	0.057 (6)*
O7	0.08547 (9)	0.65708 (9)	0.42939 (6)	0.0177 (2)
O6	−0.06310 (11)	0.78516 (10)	0.88240 (7)	0.0239 (2)
O5	0.14461 (10)	0.66456 (10)	0.89168 (7)	0.0218 (2)
O2	0.36727 (11)	0.49535 (11)	0.19050 (8)	0.0271 (2)
O4	0.34852 (12)	0.56629 (13)	0.58842 (7)	0.0356 (3)
O1	0.00907 (10)	0.66737 (10)	0.06784 (7)	0.0228 (2)
C2	0.04386 (13)	0.66487 (13)	0.25172 (9)	0.0176 (3)
H2	−0.0292	0.7038	0.2654	0.021*
O3	0.40841 (11)	0.49651 (11)	0.39194 (7)	0.0285 (2)
C9	0.16055 (13)	0.63687 (13)	0.51583 (9)	0.0173 (3)
C7	0.30868 (14)	0.54787 (14)	0.40213 (10)	0.0200 (3)
C6	0.23103 (13)	0.57569 (13)	0.31483 (9)	0.0168 (3)
C10	0.10402 (13)	0.67676 (13)	0.61167 (9)	0.0169 (3)
C11	0.15182 (13)	0.65227 (13)	0.70965 (9)	0.0167 (2)
H11	0.2240	0.6105	0.7148	0.020*
C1	0.12102 (13)	0.63166 (13)	0.33151 (9)	0.0161 (2)
C14	−0.06157 (14)	0.77377 (14)	0.69502 (10)	0.0205 (3)
H14	−0.1343	0.8150	0.6900	0.025*
C4	0.18654 (14)	0.58137 (13)	0.12986 (10)	0.0194 (3)
H4	0.2076	0.5643	0.0605	0.023*
C15	−0.00405 (14)	0.73746 (14)	0.60594 (10)	0.0200 (3)
H15	−0.0381	0.7538	0.5407	0.024*
C12	0.09419 (13)	0.68879 (13)	0.79803 (9)	0.0164 (2)
C3	0.07772 (14)	0.63890 (13)	0.15072 (9)	0.0178 (3)
C8	0.27104 (14)	0.58508 (14)	0.50414 (10)	0.0211 (3)
C5	0.26212 (14)	0.55005 (13)	0.21048 (10)	0.0185 (3)
C13	−0.01358 (13)	0.75030 (13)	0.79185 (9)	0.0175 (3)
C18	−0.47659 (14)	1.03481 (14)	0.85957 (10)	0.0216 (3)
C21	−0.58885 (14)	1.10239 (14)	0.86858 (10)	0.0215 (3)
C16	−0.24600 (15)	1.01614 (15)	0.91837 (11)	0.0267 (3)
H16	−0.1579	1.0518	0.9641	0.032*
C17	−0.34658 (15)	1.08367 (15)	0.92649 (11)	0.0251 (3)
H17	−0.3268	1.1627	0.9773	0.030*
C25	−0.72872 (15)	1.04105 (15)	0.81593 (12)	0.0276 (3)
H25	−0.7534	0.9564	0.7711	0.033*
C19	−0.49705 (16)	0.91959 (16)	0.78522 (13)	0.0317 (3)
H19	−0.5823	0.8839	0.7365	0.038*
C22	−0.56059 (16)	1.22742 (16)	0.93211 (13)	0.0340 (4)
H22	−0.4669	1.2739	0.9686	0.041*
C24	−0.83135 (16)	1.10535 (15)	0.82995 (12)	0.0291 (3)
H24	−0.9259	1.0620	0.7940	0.035*
C23	−0.67028 (17)	1.28348 (17)	0.94160 (13)	0.0357 (4)
H23	−0.6492	1.3679	0.9861	0.043*
C20	−0.39110 (17)	0.85775 (17)	0.78337 (13)	0.0346 (4)
H20	−0.4071	0.7791	0.7329	0.042*
C30	0.5486 (2)	0.8659 (2)	0.41156 (16)	0.0473 (5)
H30	0.4595	0.8225	0.3678	0.057*
C32	0.56137 (17)	0.97420 (17)	0.49022 (14)	0.0387 (4)
N3	0.79633 (17)	0.87863 (18)	0.45260 (15)	0.0531 (4)
C31	0.69687 (19)	1.03207 (19)	0.55032 (17)	0.0480 (5)
H31	0.7124	1.1049	0.6063	0.058*
C29	0.6656 (2)	0.8211 (2)	0.39678 (17)	0.0526 (5)
H29	0.6520	0.7453	0.3440	0.063*
C27	0.8085 (2)	0.9828 (2)	0.52799 (18)	0.0532 (5)
H27	0.8998	1.0260	0.5690	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0277 (6)	0.0357 (7)	0.0250 (6)	0.0205 (5)	0.0061 (5)	0.0077 (5)
N2	0.0270 (6)	0.0369 (7)	0.0282 (6)	0.0202 (6)	0.0068 (5)	0.0051 (5)
O7	0.0207 (4)	0.0283 (5)	0.0098 (4)	0.0156 (4)	0.0027 (3)	0.0039 (3)
O6	0.0286 (5)	0.0377 (6)	0.0147 (4)	0.0233 (5)	0.0066 (4)	0.0045 (4)
O5	0.0244 (5)	0.0363 (6)	0.0112 (4)	0.0181 (4)	0.0036 (4)	0.0060 (4)
O2	0.0296 (5)	0.0472 (6)	0.0163 (5)	0.0289 (5)	0.0051 (4)	0.0052 (4)
O4	0.0380 (6)	0.0741 (8)	0.0137 (5)	0.0446 (6)	0.0046 (4)	0.0090 (5)
O1	0.0272 (5)	0.0383 (6)	0.0129 (4)	0.0230 (5)	0.0044 (4)	0.0076 (4)
C2	0.0187 (6)	0.0235 (6)	0.0154 (6)	0.0136 (5)	0.0034 (5)	0.0037 (5)
O3	0.0298 (5)	0.0509 (7)	0.0173 (5)	0.0309 (5)	0.0037 (4)	0.0060 (4)
C9	0.0191 (6)	0.0239 (6)	0.0117 (5)	0.0111 (5)	0.0006 (5)	0.0037 (5)
C7	0.0198 (6)	0.0282 (7)	0.0159 (6)	0.0136 (5)	0.0023 (5)	0.0037 (5)
C6	0.0174 (6)	0.0219 (6)	0.0137 (6)	0.0103 (5)	0.0017 (5)	0.0027 (5)
C10	0.0176 (6)	0.0213 (6)	0.0137 (6)	0.0095 (5)	0.0024 (5)	0.0016 (5)
C11	0.0167 (6)	0.0206 (6)	0.0152 (6)	0.0099 (5)	0.0019 (5)	0.0024 (5)
C1	0.0181 (6)	0.0202 (6)	0.0116 (5)	0.0086 (5)	0.0030 (4)	0.0023 (5)
C14	0.0219 (6)	0.0277 (7)	0.0181 (6)	0.0164 (6)	0.0036 (5)	0.0049 (5)
C4	0.0233 (6)	0.0271 (7)	0.0116 (5)	0.0135 (5)	0.0043 (5)	0.0024 (5)
C15	0.0220 (6)	0.0280 (7)	0.0144 (6)	0.0140 (6)	0.0017 (5)	0.0053 (5)
C12	0.0176 (6)	0.0204 (6)	0.0117 (5)	0.0075 (5)	0.0003 (4)	0.0030 (5)
C3	0.0203 (6)	0.0230 (6)	0.0131 (6)	0.0108 (5)	0.0014 (5)	0.0047 (5)
C8	0.0224 (6)	0.0331 (7)	0.0128 (6)	0.0166 (6)	0.0007 (5)	0.0041 (5)
C5	0.0189 (6)	0.0240 (7)	0.0156 (6)	0.0115 (5)	0.0037 (5)	0.0023 (5)
C13	0.0187 (6)	0.0219 (6)	0.0140 (6)	0.0097 (5)	0.0040 (5)	0.0021 (5)
C18	0.0200 (6)	0.0237 (7)	0.0245 (7)	0.0106 (5)	0.0061 (5)	0.0054 (5)
C21	0.0206 (6)	0.0256 (7)	0.0228 (6)	0.0124 (5)	0.0061 (5)	0.0062 (5)
C16	0.0224 (7)	0.0350 (8)	0.0260 (7)	0.0142 (6)	0.0024 (5)	0.0054 (6)
C17	0.0237 (7)	0.0267 (7)	0.0264 (7)	0.0119 (6)	0.0022 (5)	0.0012 (6)
C25	0.0228 (7)	0.0264 (7)	0.0348 (8)	0.0119 (6)	0.0010 (6)	0.0019 (6)
C19	0.0244 (7)	0.0349 (8)	0.0352 (8)	0.0149 (6)	−0.0013 (6)	−0.0042 (6)
C22	0.0244 (7)	0.0342 (8)	0.0411 (9)	0.0140 (6)	−0.0018 (6)	−0.0070 (7)
C24	0.0223 (7)	0.0331 (8)	0.0341 (8)	0.0138 (6)	0.0004 (6)	0.0045 (6)
C23	0.0345 (8)	0.0342 (8)	0.0405 (9)	0.0210 (7)	0.0015 (7)	−0.0068 (7)
C20	0.0337 (8)	0.0358 (9)	0.0367 (8)	0.0208 (7)	0.0015 (7)	−0.0055 (7)
C30	0.0333 (9)	0.0505 (11)	0.0502 (11)	0.0012 (8)	−0.0014 (8)	0.0152 (9)
C32	0.0297 (8)	0.0348 (9)	0.0474 (10)	−0.0007 (7)	−0.0031 (7)	0.0232 (8)
N3	0.0408 (9)	0.0551 (11)	0.0686 (11)	0.0151 (8)	0.0016 (8)	0.0311 (9)
C31	0.0343 (9)	0.0394 (10)	0.0631 (12)	0.0034 (8)	−0.0113 (8)	0.0151 (9)
C29	0.0457 (11)	0.0518 (12)	0.0586 (12)	0.0098 (9)	0.0055 (9)	0.0180 (10)
C27	0.0337 (9)	0.0517 (12)	0.0708 (14)	0.0072 (8)	−0.0112 (9)	0.0244 (11)

Geometric parameters (Å, º)

N1—C24	1.337 (2)	C4—C5	1.3798 (18)
N1—C23	1.339 (2)	C4—C3	1.4138 (18)
N2—C16	1.337 (2)	C4—H4	0.9500
N2—C20	1.347 (2)	C15—H15	0.9500
O7—C1	1.3646 (15)	C12—C13	1.4104 (18)
O7—C9	1.3796 (15)	C18—C17	1.397 (2)
O6—C13	1.3612 (16)	C18—C19	1.399 (2)
O6—H6O	0.91 (2)	C18—C21	1.4959 (18)
O5—C12	1.3725 (15)	C21—C22	1.397 (2)
O5—H5O	0.85 (2)	C21—C25	1.400 (2)
O2—C5	1.3597 (16)	C16—C17	1.3930 (19)
O2—H2O	0.90 (2)	C16—H16	0.9500
O4—C8	1.3631 (16)	C17—H17	0.9500
O4—H4O	0.87 (2)	C25—C24	1.393 (2)
O1—C3	1.3511 (15)	C25—H25	0.9500
O1—H1O	0.92 (2)	C19—C20	1.394 (2)
C2—C1	1.3909 (17)	C19—H19	0.9500
C2—C3	1.3972 (18)	C22—C23	1.391 (2)
C2—H2	0.9500	C22—H22	0.9500
O3—C7	1.2691 (16)	C24—H24	0.9500
C9—C8	1.3716 (18)	C23—H23	0.9500
C9—C10	1.4705 (18)	C20—H20	0.9500
C7—C6	1.4391 (17)	C30—C29	1.392 (3)
C7—C8	1.4453 (18)	C30—C32	1.395 (3)
C6—C1	1.4044 (17)	C30—H30	0.9500
C6—C5	1.4280 (18)	C32—C31	1.400 (2)
C10—C15	1.4067 (18)	C32—C32^i	1.498 (4)
C10—C11	1.4160 (18)	N3—C29	1.341 (3)
C11—C12	1.3851 (18)	N3—C27	1.341 (3)
C11—H11	0.9500	C31—C27	1.389 (3)
C14—C15	1.3914 (18)	C31—H31	0.9500
C14—C13	1.3985 (18)	C29—H29	0.9500
C14—H14	0.9500	C27—H27	0.9500
C24—N1—C23	117.02 (12)	O6—C13—C14	123.95 (11)
C16—N2—C20	117.11 (12)	O6—C13—C12	117.06 (11)
C1—O7—C9	121.92 (10)	C14—C13—C12	118.98 (11)
C13—O6—H6O	107.9 (13)	C17—C18—C19	116.98 (12)
C12—O5—H5O	110.1 (13)	C17—C18—C21	121.07 (13)
C5—O2—H2O	105.1 (13)	C19—C18—C21	121.94 (13)
C8—O4—H4O	111.6 (14)	C22—C21—C25	116.88 (12)
C3—O1—H1O	112.5 (13)	C22—C21—C18	121.75 (13)
C1—C2—C3	117.54 (11)	C25—C21—C18	121.34 (13)
C1—C2—H2	121.2	N2—C16—C17	123.35 (13)
C3—C2—H2	121.2	N2—C16—H16	118.3
C8—C9—O7	119.89 (11)	C17—C16—H16	118.3
C8—C9—C10	129.17 (11)	C16—C17—C18	119.77 (13)
O7—C9—C10	110.95 (10)	C16—C17—H17	120.1
O3—C7—C6	122.50 (12)	C18—C17—H17	120.1
O3—C7—C8	120.67 (11)	C24—C25—C21	119.35 (14)
C6—C7—C8	116.81 (11)	C24—C25—H25	120.3
C1—C6—C5	117.83 (11)	C21—C25—H25	120.3
C1—C6—C7	119.57 (11)	C20—C19—C18	119.36 (14)
C5—C6—C7	122.60 (11)	C20—C19—H19	120.3
C15—C10—C11	118.62 (11)	C18—C19—H19	120.3
C15—C10—C9	119.32 (11)	C23—C22—C21	119.64 (14)
C11—C10—C9	122.03 (11)	C23—C22—H22	120.2
C12—C11—C10	120.51 (11)	C21—C22—H22	120.2
C12—C11—H11	119.7	N1—C24—C25	123.63 (14)
C10—C11—H11	119.7	N1—C24—H24	118.2
O7—C1—C2	116.52 (11)	C25—C24—H24	118.2
O7—C1—C6	120.47 (11)	N1—C23—C22	123.48 (15)
C2—C1—C6	123.01 (11)	N1—C23—H23	118.3
C15—C14—C13	120.74 (12)	C22—C23—H23	118.3
C15—C14—H14	119.6	N2—C20—C19	123.39 (14)
C13—C14—H14	119.6	N2—C20—H20	118.3
C5—C4—C3	119.82 (11)	C19—C20—H20	118.3
C5—C4—H4	120.1	C29—C30—C32	120.39 (17)
C3—C4—H4	120.1	C29—C30—H30	119.8
C14—C15—C10	120.56 (11)	C32—C30—H30	119.8
C14—C15—H15	119.7	C30—C32—C31	115.68 (18)
C10—C15—H15	119.7	C30—C32—C32^i	122.51 (19)
O5—C12—C11	118.67 (11)	C31—C32—C32^i	121.8 (2)
O5—C12—C13	120.75 (11)	C29—N3—C27	115.58 (18)
C11—C12—C13	120.58 (11)	C27—C31—C32	119.9 (2)
O1—C3—C2	122.15 (11)	C27—C31—H31	120.1
O1—C3—C4	116.32 (11)	C32—C31—H31	120.1
C2—C3—C4	121.52 (11)	N3—C29—C30	123.9 (2)
O4—C8—C9	121.06 (11)	N3—C29—H29	118.0
O4—C8—C7	117.77 (11)	C30—C29—H29	118.0
C9—C8—C7	121.17 (11)	N3—C27—C31	124.52 (18)
O2—C5—C4	119.81 (11)	N3—C27—H27	117.7
O2—C5—C6	119.91 (11)	C31—C27—H27	117.7
C4—C5—C6	120.28 (11)

Symmetry code: (i) −x+1, −y+2, −z+1.

(QBP_IV)

Crystal data

C45H36N6O8	V = 1860.6 (4) Å^3
Mr = 788.80	Z = 2
Triclinic, P1	F(000) = 824
a = 10.0222 (12) Å	Dx = 1.408 Mg m^−3
b = 12.8756 (16) Å	Mo Kα radiation, λ = 0.71073 Å
c = 15.0597 (18) Å	µ = 0.10 mm^−1
α = 81.685 (6)°	T = 150 K
β = 83.118 (6)°	Plate, yellow
γ = 76.273 (5)°	0.65 × 0.50 × 0.25 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.031
Tmin = 0.804, Tmax = 1.000	θmax = 27.5°, θmin = 3.0°
19338 measured reflections	h = −13→12
8502 independent reflections	k = −16→16
6720 reflections with I > 2σ(I)	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0836P)^2 + 0.7989P] where P = (Fo^2 + 2Fc^2)/3
S = 0.88	(Δ/σ)max = 0.001
8502 reflections	Δρmax = 0.31 e Å^−3
560 parameters	Δρmin = −0.21 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
O8	0.75617 (12)	0.56108 (11)	0.16403 (10)	0.0418 (3)
H6O	0.595 (2)	0.6117 (18)	0.1188 (15)	0.055 (6)*
H4O	−0.180 (2)	0.9253 (19)	0.2227 (15)	0.060 (7)*
H5O	0.173 (3)	0.7484 (19)	0.0209 (15)	0.061 (7)*
H1O	0.137 (3)	0.832 (2)	0.7270 (16)	0.072 (7)*
H2O	−0.340 (2)	0.9677 (17)	0.4786 (16)	0.054 (6)*
H8A	0.834 (3)	0.528 (2)	0.1363 (16)	0.062 (7)*
H8B	0.774 (3)	0.554 (2)	0.224 (2)	0.085 (9)*
C1	0.03344 (14)	0.85523 (10)	0.48247 (9)	0.0188 (3)
C2	0.08743 (14)	0.84369 (11)	0.56460 (9)	0.0209 (3)
H2	0.1829	0.8153	0.5706	0.025*
C3	−0.00402 (15)	0.87539 (11)	0.63830 (9)	0.0222 (3)
C4	−0.14506 (15)	0.91790 (11)	0.62952 (10)	0.0241 (3)
H4	−0.2051	0.9399	0.6805	0.029*
C5	−0.19632 (14)	0.92775 (11)	0.54738 (9)	0.0222 (3)
C6	−0.10671 (14)	0.89630 (10)	0.47079 (9)	0.0196 (3)
C7	−0.15483 (14)	0.90758 (11)	0.38322 (9)	0.0217 (3)
C8	−0.05135 (14)	0.87577 (11)	0.31030 (9)	0.0210 (3)
C9	0.08289 (14)	0.83165 (10)	0.32688 (9)	0.0189 (3)
C10	0.19848 (13)	0.78637 (10)	0.26419 (9)	0.0183 (3)
C11	0.17967 (13)	0.77746 (11)	0.17490 (9)	0.0198 (3)
H11	0.0914	0.8060	0.1533	0.024*
C12	0.28689 (14)	0.72805 (11)	0.11764 (9)	0.0199 (3)
C13	0.41857 (13)	0.68535 (11)	0.14859 (9)	0.0201 (3)
C14	0.43743 (14)	0.69521 (11)	0.23640 (9)	0.0219 (3)
H14	0.5261	0.6677	0.2576	0.026*
C15	0.32986 (14)	0.74443 (11)	0.29424 (9)	0.0208 (3)
H15	0.3454	0.7497	0.3543	0.025*
C26	−0.36115 (14)	1.07102 (12)	0.10190 (10)	0.0247 (3)
H26	−0.2865	1.1036	0.0784	0.030*
C27	−0.48688 (14)	1.11209 (12)	0.06654 (9)	0.0223 (3)
H27	−0.4976	1.1721	0.0211	0.027*
C28	−0.59767 (13)	1.06476 (11)	0.09806 (9)	0.0188 (3)
C29	−0.57329 (15)	0.97705 (12)	0.16457 (10)	0.0269 (3)
H29	−0.6446	0.9407	0.1875	0.032*
C30	−0.44450 (16)	0.94305 (13)	0.19719 (11)	0.0296 (3)
H30	−0.4310	0.8842	0.2436	0.035*
C31	−0.73626 (13)	1.10646 (11)	0.06445 (9)	0.0190 (3)
C35	−0.76145 (15)	1.19159 (12)	−0.00436 (10)	0.0272 (3)
H35	−0.6883	1.2229	−0.0333	0.033*
C34	−0.89365 (16)	1.23008 (13)	−0.03011 (11)	0.0312 (3)
H34	−0.9083	1.2878	−0.0775	0.037*
C33	−0.97755 (15)	1.10894 (14)	0.07216 (11)	0.0310 (3)
H33	−1.0527	1.0791	0.0995	0.037*
C32	−0.84867 (15)	1.06439 (13)	0.10198 (10)	0.0278 (3)
H32	−0.8370	1.0051	0.1481	0.033*
N3	−0.33830 (12)	0.98844 (10)	0.16700 (8)	0.0247 (3)
N4	−1.00225 (13)	1.19122 (11)	0.00748 (8)	0.0281 (3)
O1	0.03813 (11)	0.86759 (9)	0.72072 (7)	0.0292 (2)
O2	−0.33269 (11)	0.96839 (9)	0.53943 (8)	0.0314 (3)
O3	−0.27940 (10)	0.94225 (9)	0.36894 (7)	0.0297 (2)
O4	−0.09149 (11)	0.88677 (9)	0.22658 (7)	0.0300 (3)
O5	0.26954 (10)	0.71790 (9)	0.03150 (7)	0.0266 (2)
O6	0.51954 (10)	0.63680 (9)	0.08952 (7)	0.0266 (2)
O7	0.12378 (9)	0.82190 (8)	0.41195 (6)	0.0203 (2)
C40	0.58922 (17)	0.19344 (13)	0.29587 (10)	0.0309 (3)
H40	0.6020	0.1385	0.3455	0.037*
C39	0.45736 (16)	0.23515 (12)	0.27093 (10)	0.0268 (3)
H39	0.3819	0.2094	0.3032	0.032*
C38	0.43552 (14)	0.31553 (11)	0.19788 (9)	0.0222 (3)
C37	0.55130 (16)	0.34889 (13)	0.15379 (11)	0.0295 (3)
H37	0.5422	0.4029	0.1034	0.035*
C36	0.67927 (16)	0.30271 (14)	0.18398 (11)	0.0325 (3)
H36	0.7569	0.3268	0.1533	0.039*
C41	0.29549 (14)	0.36182 (11)	0.16778 (9)	0.0217 (3)
C45	0.18479 (16)	0.31500 (12)	0.20007 (11)	0.0281 (3)
H45	0.1980	0.2509	0.2412	0.034*
C44	0.05554 (16)	0.36218 (14)	0.17212 (12)	0.0331 (4)
H44	−0.0187	0.3293	0.1959	0.040*
C43	0.13559 (16)	0.49480 (13)	0.08118 (11)	0.0332 (4)
H43	0.1195	0.5573	0.0384	0.040*
C42	0.26868 (15)	0.45432 (12)	0.10609 (10)	0.0279 (3)
H42	0.3407	0.4892	0.0814	0.033*
N5	0.70001 (14)	0.22607 (11)	0.25395 (9)	0.0313 (3)
N6	0.02873 (13)	0.45116 (12)	0.11372 (9)	0.0334 (3)
C23	1.4491 (2)	0.27893 (17)	0.51380 (13)	0.0467 (5)
H23	1.4682	0.2159	0.5558	0.056*
C22	1.31420 (19)	0.31732 (15)	0.49139 (12)	0.0406 (4)
H22	1.2442	0.2816	0.5188	0.049*
C21	1.28183 (16)	0.40760 (12)	0.42921 (10)	0.0278 (3)
C25	1.38970 (19)	0.45547 (14)	0.39453 (15)	0.0448 (5)
H25	1.3740	0.5182	0.3519	0.054*
C24	1.5205 (2)	0.41221 (16)	0.42172 (17)	0.0533 (5)
H24	1.5919	0.4475	0.3967	0.064*
C18	1.14084 (16)	0.44901 (12)	0.39878 (10)	0.0260 (3)
C17	1.03657 (17)	0.39380 (13)	0.42374 (12)	0.0358 (4)
H17	1.0528	0.3286	0.4635	0.043*
C16	0.90907 (18)	0.43356 (14)	0.39083 (13)	0.0403 (4)
H16	0.8396	0.3941	0.4097	0.048*
C20	0.9774 (2)	0.57746 (15)	0.31187 (13)	0.0430 (4)
H20	0.9578	0.6432	0.2731	0.052*
C19	1.1078 (2)	0.54378 (14)	0.34126 (12)	0.0401 (4)
H19	1.1747	0.5855	0.3221	0.048*
N2	1.55306 (16)	0.32453 (13)	0.48045 (12)	0.0462 (4)
N1	0.87720 (15)	0.52385 (12)	0.33425 (10)	0.0374 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O8	0.0195 (6)	0.0570 (8)	0.0425 (7)	0.0062 (5)	−0.0085 (5)	−0.0050 (6)
C1	0.0184 (6)	0.0151 (6)	0.0216 (6)	−0.0038 (5)	−0.0007 (5)	0.0007 (5)
C2	0.0194 (6)	0.0206 (6)	0.0227 (7)	−0.0045 (5)	−0.0039 (5)	−0.0008 (5)
C3	0.0244 (7)	0.0216 (7)	0.0210 (7)	−0.0065 (5)	−0.0039 (5)	0.0006 (5)
C4	0.0237 (7)	0.0242 (7)	0.0222 (7)	−0.0041 (6)	0.0015 (5)	−0.0004 (5)
C5	0.0167 (6)	0.0209 (7)	0.0260 (7)	−0.0015 (5)	−0.0008 (5)	0.0013 (5)
C6	0.0177 (6)	0.0178 (6)	0.0219 (7)	−0.0035 (5)	−0.0027 (5)	0.0023 (5)
C7	0.0176 (6)	0.0197 (6)	0.0254 (7)	−0.0016 (5)	−0.0034 (5)	0.0017 (5)
C8	0.0192 (6)	0.0225 (6)	0.0199 (6)	−0.0025 (5)	−0.0049 (5)	0.0006 (5)
C9	0.0189 (6)	0.0189 (6)	0.0189 (6)	−0.0046 (5)	−0.0043 (5)	0.0005 (5)
C10	0.0155 (6)	0.0183 (6)	0.0206 (6)	−0.0047 (5)	−0.0023 (5)	0.0013 (5)
C11	0.0142 (6)	0.0214 (6)	0.0230 (7)	−0.0027 (5)	−0.0048 (5)	0.0007 (5)
C12	0.0185 (6)	0.0215 (6)	0.0193 (6)	−0.0047 (5)	−0.0044 (5)	0.0021 (5)
C13	0.0152 (6)	0.0204 (6)	0.0228 (7)	−0.0034 (5)	−0.0006 (5)	0.0017 (5)
C14	0.0145 (6)	0.0245 (7)	0.0253 (7)	−0.0026 (5)	−0.0064 (5)	0.0026 (5)
C15	0.0196 (6)	0.0225 (7)	0.0206 (6)	−0.0050 (5)	−0.0065 (5)	0.0006 (5)
C26	0.0168 (6)	0.0325 (8)	0.0249 (7)	−0.0054 (6)	−0.0030 (5)	−0.0034 (6)
C27	0.0201 (7)	0.0275 (7)	0.0190 (6)	−0.0058 (6)	−0.0030 (5)	0.0001 (5)
C28	0.0167 (6)	0.0205 (6)	0.0198 (6)	−0.0017 (5)	−0.0042 (5)	−0.0059 (5)
C29	0.0203 (7)	0.0271 (7)	0.0327 (8)	−0.0074 (6)	−0.0081 (6)	0.0063 (6)
C30	0.0239 (7)	0.0281 (8)	0.0354 (8)	−0.0044 (6)	−0.0120 (6)	0.0059 (6)
C31	0.0163 (6)	0.0220 (6)	0.0189 (6)	−0.0027 (5)	−0.0039 (5)	−0.0042 (5)
C35	0.0208 (7)	0.0311 (8)	0.0278 (7)	−0.0058 (6)	−0.0050 (6)	0.0054 (6)
C34	0.0246 (8)	0.0354 (8)	0.0292 (8)	−0.0015 (6)	−0.0084 (6)	0.0066 (6)
C33	0.0177 (7)	0.0440 (9)	0.0310 (8)	−0.0094 (6)	−0.0061 (6)	0.0033 (7)
C32	0.0201 (7)	0.0331 (8)	0.0291 (8)	−0.0071 (6)	−0.0079 (6)	0.0068 (6)
N3	0.0171 (6)	0.0286 (6)	0.0279 (6)	−0.0005 (5)	−0.0071 (5)	−0.0051 (5)
N4	0.0185 (6)	0.0389 (7)	0.0252 (6)	−0.0008 (5)	−0.0082 (5)	−0.0029 (5)
O1	0.0273 (6)	0.0388 (6)	0.0200 (5)	−0.0036 (5)	−0.0048 (4)	−0.0029 (4)
O2	0.0180 (5)	0.0429 (7)	0.0271 (6)	0.0029 (5)	−0.0006 (4)	−0.0013 (5)
O3	0.0164 (5)	0.0396 (6)	0.0278 (5)	0.0033 (4)	−0.0051 (4)	0.0003 (5)
O4	0.0173 (5)	0.0447 (7)	0.0230 (5)	0.0061 (5)	−0.0073 (4)	−0.0048 (5)
O5	0.0190 (5)	0.0379 (6)	0.0204 (5)	−0.0012 (4)	−0.0039 (4)	−0.0024 (4)
O6	0.0151 (5)	0.0352 (6)	0.0252 (5)	0.0019 (4)	−0.0019 (4)	−0.0023 (4)
O7	0.0160 (4)	0.0247 (5)	0.0189 (5)	−0.0017 (4)	−0.0032 (4)	−0.0019 (4)
C40	0.0340 (8)	0.0305 (8)	0.0248 (7)	0.0013 (7)	−0.0083 (6)	−0.0009 (6)
C39	0.0278 (7)	0.0263 (7)	0.0244 (7)	−0.0029 (6)	−0.0034 (6)	−0.0016 (6)
C38	0.0223 (7)	0.0217 (7)	0.0225 (7)	−0.0014 (5)	−0.0051 (5)	−0.0051 (5)
C37	0.0247 (7)	0.0311 (8)	0.0315 (8)	−0.0063 (6)	−0.0071 (6)	0.0042 (6)
C36	0.0230 (7)	0.0405 (9)	0.0340 (8)	−0.0075 (7)	−0.0065 (6)	−0.0008 (7)
C41	0.0199 (7)	0.0238 (7)	0.0215 (7)	−0.0024 (5)	−0.0033 (5)	−0.0061 (5)
C45	0.0250 (7)	0.0267 (7)	0.0327 (8)	−0.0067 (6)	−0.0048 (6)	−0.0005 (6)
C44	0.0218 (7)	0.0372 (9)	0.0411 (9)	−0.0078 (6)	−0.0046 (6)	−0.0038 (7)
C43	0.0266 (8)	0.0339 (8)	0.0342 (8)	0.0004 (7)	−0.0059 (6)	0.0026 (7)
C42	0.0224 (7)	0.0292 (8)	0.0295 (8)	−0.0036 (6)	−0.0021 (6)	0.0012 (6)
N5	0.0266 (7)	0.0366 (7)	0.0297 (7)	0.0006 (6)	−0.0113 (5)	−0.0064 (6)
N6	0.0222 (6)	0.0383 (8)	0.0370 (7)	−0.0003 (6)	−0.0068 (6)	−0.0032 (6)
C23	0.0486 (11)	0.0497 (11)	0.0427 (10)	−0.0101 (9)	−0.0229 (9)	0.0059 (8)
C22	0.0419 (10)	0.0451 (10)	0.0374 (9)	−0.0172 (8)	−0.0148 (8)	0.0082 (8)
C21	0.0317 (8)	0.0256 (7)	0.0283 (7)	−0.0076 (6)	−0.0046 (6)	−0.0073 (6)
C25	0.0339 (9)	0.0280 (8)	0.0701 (13)	−0.0085 (7)	−0.0059 (9)	0.0052 (8)
C24	0.0318 (10)	0.0404 (10)	0.0885 (16)	−0.0114 (8)	−0.0089 (10)	−0.0018 (10)
C18	0.0310 (8)	0.0221 (7)	0.0266 (7)	−0.0079 (6)	−0.0037 (6)	−0.0048 (6)
C17	0.0328 (9)	0.0269 (8)	0.0454 (10)	−0.0068 (7)	−0.0043 (7)	0.0044 (7)
C16	0.0299 (9)	0.0330 (9)	0.0575 (11)	−0.0091 (7)	−0.0053 (8)	0.0014 (8)
C20	0.0503 (11)	0.0331 (9)	0.0478 (10)	−0.0133 (8)	−0.0220 (9)	0.0088 (8)
C19	0.0448 (10)	0.0344 (9)	0.0463 (10)	−0.0203 (8)	−0.0195 (8)	0.0106 (7)
N2	0.0386 (8)	0.0445 (9)	0.0592 (10)	−0.0070 (7)	−0.0182 (8)	−0.0106 (8)
N1	0.0337 (8)	0.0334 (7)	0.0451 (8)	−0.0035 (6)	−0.0118 (6)	−0.0050 (6)

Geometric parameters (Å, º)

O8—H8A	0.88 (3)	C33—H33	0.9500
O8—H8B	0.93 (3)	C32—H32	0.9500
C1—O7	1.3597 (16)	O1—H1O	1.00 (3)
C1—C2	1.3833 (19)	O2—H2O	0.93 (2)
C1—C6	1.4012 (18)	O4—H4O	0.91 (2)
C2—C3	1.3957 (19)	O5—H5O	0.98 (2)
C2—H2	0.9500	O6—H6O	0.89 (2)
C3—O1	1.3411 (17)	C40—N5	1.336 (2)
C3—C4	1.4042 (19)	C40—C39	1.378 (2)
C4—C5	1.373 (2)	C40—H40	0.9500
C4—H4	0.9500	C39—C38	1.396 (2)
C5—O2	1.3557 (16)	C39—H39	0.9500
C5—C6	1.4195 (19)	C38—C37	1.393 (2)
C6—C7	1.4341 (19)	C38—C41	1.4858 (19)
C7—O3	1.2555 (16)	C37—C36	1.380 (2)
C7—C8	1.4508 (19)	C37—H37	0.9500
C8—O4	1.3470 (16)	C36—N5	1.335 (2)
C8—C9	1.3681 (18)	C36—H36	0.9500
C9—O7	1.3711 (15)	C41—C45	1.391 (2)
C9—C10	1.4663 (18)	C41—C42	1.393 (2)
C10—C15	1.4017 (18)	C45—C44	1.381 (2)
C10—C11	1.4044 (19)	C45—H45	0.9500
C11—C12	1.3839 (19)	C44—N6	1.333 (2)
C11—H11	0.9500	C44—H44	0.9500
C12—O5	1.3580 (17)	C43—N6	1.335 (2)
C12—C13	1.4107 (18)	C43—C42	1.387 (2)
C13—O6	1.3605 (16)	C43—H43	0.9500
C13—C14	1.3859 (19)	C42—H42	0.9500
C14—C15	1.390 (2)	C23—N2	1.327 (3)
C14—H14	0.9500	C23—C22	1.389 (3)
C15—H15	0.9500	C23—H23	0.9500
C26—N3	1.3345 (19)	C22—C21	1.383 (2)
C26—C27	1.3836 (19)	C22—H22	0.9500
C26—H26	0.9500	C21—C25	1.382 (2)
C27—C28	1.3931 (19)	C21—C18	1.489 (2)
C27—H27	0.9500	C25—C24	1.383 (3)
C28—C29	1.3924 (19)	C25—H25	0.9500
C28—C31	1.4865 (18)	C24—N2	1.330 (3)
C29—C30	1.386 (2)	C24—H24	0.9500
C29—H29	0.9500	C18—C17	1.386 (2)
C30—N3	1.335 (2)	C18—C19	1.386 (2)
C30—H30	0.9500	C17—C16	1.382 (2)
C31—C32	1.389 (2)	C17—H17	0.9500
C31—C35	1.3935 (19)	C16—N1	1.335 (2)
C35—C34	1.381 (2)	C16—H16	0.9500
C35—H35	0.9500	C20—N1	1.334 (2)
C34—N4	1.336 (2)	C20—C19	1.380 (2)
C34—H34	0.9500	C20—H20	0.9500
C33—N4	1.329 (2)	C19—H19	0.9500
C33—C32	1.383 (2)
H8A—O8—H8B	105 (2)	C33—C32—H32	120.0
O7—C1—C2	116.37 (12)	C31—C32—H32	120.0
O7—C1—C6	120.46 (12)	C26—N3—C30	116.49 (12)
C2—C1—C6	123.15 (12)	C33—N4—C34	116.37 (13)
C1—C2—C3	117.32 (12)	C3—O1—H1O	115.7 (14)
C1—C2—H2	121.3	C5—O2—H2O	103.1 (14)
C3—C2—H2	121.3	C8—O4—H4O	112.4 (14)
O1—C3—C2	121.90 (13)	C12—O5—H5O	108.5 (13)
O1—C3—C4	116.63 (13)	C13—O6—H6O	107.2 (15)
C2—C3—C4	121.46 (13)	C1—O7—C9	121.63 (10)
C5—C4—C3	120.09 (13)	N5—C40—C39	123.52 (14)
C5—C4—H4	120.0	N5—C40—H40	118.2
C3—C4—H4	120.0	C39—C40—H40	118.2
O2—C5—C4	119.82 (13)	C40—C39—C38	119.52 (14)
O2—C5—C6	120.01 (12)	C40—C39—H39	120.2
C4—C5—C6	120.17 (12)	C38—C39—H39	120.2
C1—C6—C5	117.80 (12)	C37—C38—C39	116.91 (13)
C1—C6—C7	120.01 (12)	C37—C38—C41	121.68 (13)
C5—C6—C7	122.18 (12)	C39—C38—C41	121.41 (13)
O3—C7—C6	122.84 (13)	C36—C37—C38	119.41 (14)
O3—C7—C8	120.74 (13)	C36—C37—H37	120.3
C6—C7—C8	116.42 (12)	C38—C37—H37	120.3
O4—C8—C9	120.80 (12)	N5—C36—C37	123.64 (15)
O4—C8—C7	118.47 (12)	N5—C36—H36	118.2
C9—C8—C7	120.67 (12)	C37—C36—H36	118.2
C8—C9—O7	120.65 (12)	C45—C41—C42	116.81 (13)
C8—C9—C10	128.57 (12)	C45—C41—C38	121.55 (13)
O7—C9—C10	110.75 (11)	C42—C41—C38	121.64 (13)
C15—C10—C11	118.24 (12)	C44—C45—C41	119.70 (14)
C15—C10—C9	120.13 (12)	C44—C45—H45	120.1
C11—C10—C9	121.51 (12)	C41—C45—H45	120.1
C12—C11—C10	121.43 (12)	N6—C44—C45	123.87 (15)
C12—C11—H11	119.3	N6—C44—H44	118.1
C10—C11—H11	119.3	C45—C44—H44	118.1
O5—C12—C11	121.95 (12)	N6—C43—C42	123.95 (15)
O5—C12—C13	118.06 (12)	N6—C43—H43	118.0
C11—C12—C13	119.99 (12)	C42—C43—H43	118.0
O6—C13—C14	124.12 (12)	C43—C42—C41	119.21 (14)
O6—C13—C12	117.33 (12)	C43—C42—H42	120.4
C14—C13—C12	118.54 (12)	C41—C42—H42	120.4
C13—C14—C15	121.64 (12)	C36—N5—C40	117.01 (13)
C13—C14—H14	119.2	C44—N6—C43	116.43 (13)
C15—C14—H14	119.2	N2—C23—C22	124.35 (18)
C14—C15—C10	120.15 (12)	N2—C23—H23	117.8
C14—C15—H15	119.9	C22—C23—H23	117.8
C10—C15—H15	119.9	C21—C22—C23	119.95 (17)
N3—C26—C27	123.98 (13)	C21—C22—H22	120.0
N3—C26—H26	118.0	C23—C22—H22	120.0
C27—C26—H26	118.0	C25—C21—C22	115.86 (15)
C26—C27—C28	119.51 (13)	C25—C21—C18	121.71 (15)
C26—C27—H27	120.2	C22—C21—C18	122.40 (15)
C28—C27—H27	120.2	C21—C25—C24	120.09 (17)
C29—C28—C27	116.63 (12)	C21—C25—H25	120.0
C29—C28—C31	121.15 (12)	C24—C25—H25	120.0
C27—C28—C31	122.21 (12)	N2—C24—C25	124.51 (18)
C30—C29—C28	119.71 (13)	N2—C24—H24	117.7
C30—C29—H29	120.1	C25—C24—H24	117.7
C28—C29—H29	120.1	C17—C18—C19	116.09 (15)
N3—C30—C29	123.66 (14)	C17—C18—C21	122.26 (14)
N3—C30—H30	118.2	C19—C18—C21	121.62 (14)
C29—C30—H30	118.2	C16—C17—C18	120.00 (15)
C32—C31—C35	116.44 (12)	C16—C17—H17	120.0
C32—C31—C28	121.55 (12)	C18—C17—H17	120.0
C35—C31—C28	121.99 (12)	N1—C16—C17	124.23 (16)
C34—C35—C31	119.43 (14)	N1—C16—H16	117.9
C34—C35—H35	120.3	C17—C16—H16	117.9
C31—C35—H35	120.3	N1—C20—C19	124.40 (16)
N4—C34—C35	124.06 (14)	N1—C20—H20	117.8
N4—C34—H34	118.0	C19—C20—H20	117.8
C35—C34—H34	118.0	C20—C19—C18	119.92 (16)
N4—C33—C32	123.74 (14)	C20—C19—H19	120.0
N4—C33—H33	118.1	C18—C19—H19	120.0
C32—C33—H33	118.1	C23—N2—C24	115.22 (16)
C33—C32—C31	119.93 (13)	C20—N1—C16	115.34 (15)

(QDP_I)

Crystal data

C31H28N2O9	V = 1367.8 (2) Å^3
Mr = 572.55	Z = 2
Triclinic, P1	F(000) = 600
a = 10.1899 (9) Å	Dx = 1.390 Mg m^−3
b = 11.6532 (11) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.0214 (12) Å	µ = 0.10 mm^−1
α = 97.351 (7)°	T = 150 K
β = 95.446 (7)°	Plate, yellow
γ = 115.237 (8)°	0.50 × 0.25 × 0.15 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.035
Tmin = 0.818, Tmax = 1.000	θmax = 27.5°, θmin = 3.2°
14650 measured reflections	h = −13→13
6248 independent reflections	k = −15→15
4498 reflections with I > 2σ(I)	l = −16→16

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) = 0.132	w = 1/[σ^2(Fo^2) + (0.0598P)^2 + 0.4848P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
6248 reflections	Δρmax = 0.28 e Å^−3
407 parameters	Δρmin = −0.23 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
O4	0.35328 (15)	0.05476 (13)	0.09077 (9)	0.0271 (3)
O7	0.11320 (12)	0.14386 (11)	−0.06881 (8)	0.0195 (3)
O3	0.40849 (14)	0.00032 (13)	−0.10365 (9)	0.0260 (3)
O1	0.03938 (15)	0.15683 (13)	−0.43080 (9)	0.0270 (3)
O5	0.17883 (15)	0.16402 (14)	0.39659 (9)	0.0274 (3)
O6	−0.00814 (15)	0.27378 (13)	0.38164 (9)	0.0276 (3)
O2	0.37686 (15)	0.01072 (14)	−0.30471 (10)	0.0298 (3)
C9	0.18247 (18)	0.12430 (16)	0.01843 (12)	0.0177 (3)
C2	0.07294 (19)	0.15191 (16)	−0.24689 (12)	0.0201 (4)
H2	0.0042	0.1849	−0.2338	0.024*
C6	0.24734 (18)	0.07437 (16)	−0.18198 (12)	0.0184 (3)
C10	0.13392 (18)	0.16309 (16)	0.11366 (12)	0.0176 (3)
C7	0.31675 (18)	0.04606 (16)	−0.09501 (13)	0.0186 (3)
C4	0.20703 (19)	0.08420 (17)	−0.36681 (13)	0.0222 (4)
H4	0.2277	0.0716	−0.4358	0.027*
N1	0.15995 (19)	0.75960 (17)	0.39455 (12)	0.0324 (4)
C8	0.28177 (18)	0.07560 (16)	0.00676 (12)	0.0191 (4)
C11	0.17951 (18)	0.14431 (16)	0.21328 (12)	0.0185 (3)
H11	0.2437	0.1049	0.2201	0.022*
C1	0.14506 (18)	0.12250 (16)	−0.16664 (12)	0.0169 (3)
N2	0.79557 (18)	0.36859 (16)	0.34805 (12)	0.0298 (4)
C14	−0.01013 (19)	0.25805 (17)	0.19431 (13)	0.0219 (4)
H14	−0.0746	0.2972	0.1877	0.026*
C12	0.13140 (18)	0.18292 (17)	0.30097 (12)	0.0188 (3)
C24	0.2373 (2)	0.6028 (2)	0.32310 (15)	0.0314 (4)
H24	0.2152	0.5266	0.2742	0.038*
C17	0.5682 (2)	0.35796 (19)	0.26865 (16)	0.0315 (4)
H17	0.4830	0.3146	0.2161	0.038*
C22	0.4834 (2)	0.61773 (19)	0.39464 (15)	0.0273 (4)
C5	0.27738 (19)	0.05605 (17)	−0.28562 (13)	0.0204 (4)
C21	0.4760 (2)	0.5154 (2)	0.33149 (16)	0.0289 (4)
C23	0.3719 (2)	0.66556 (18)	0.39126 (14)	0.0249 (4)
C18	0.5879 (2)	0.46780 (18)	0.33836 (15)	0.0255 (4)
C3	0.10430 (19)	0.13167 (17)	−0.34740 (13)	0.0206 (4)
C13	0.03551 (19)	0.24001 (16)	0.29242 (13)	0.0194 (4)
C19	0.7163 (2)	0.52659 (19)	0.41278 (14)	0.0280 (4)
H19	0.7356	0.6019	0.4619	0.034*
C15	0.03747 (19)	0.21956 (17)	0.10638 (13)	0.0214 (4)
H15	0.0042	0.2316	0.0398	0.026*
C27	0.3966 (2)	0.77736 (19)	0.46033 (15)	0.0301 (4)
H27	0.4869	0.8240	0.5078	0.036*
C16	0.6731 (2)	0.31271 (19)	0.27634 (16)	0.0318 (4)
H16	0.6573	0.2379	0.2281	0.038*
C20	0.8146 (2)	0.4746 (2)	0.41439 (15)	0.0299 (4)
H20	0.9014	0.5163	0.4657	0.036*
C26	0.2891 (2)	0.8199 (2)	0.45930 (15)	0.0342 (5)
H26	0.3079	0.8960	0.5072	0.041*
C25	0.1369 (2)	0.6529 (2)	0.32769 (15)	0.0331 (5)
H25	0.0460	0.6091	0.2807	0.040*
O9	0.3638 (2)	0.5450 (2)	0.08366 (15)	0.0695 (6)
O8	0.1964 (2)	0.6054 (2)	−0.06407 (16)	0.0720 (6)
C28	0.3849 (3)	0.6714 (3)	0.0861 (2)	0.0681 (8)
H28A	0.4638	0.7146	0.0457	0.082*
H28B	0.4174	0.7188	0.1597	0.082*
C29	0.2492 (4)	0.6771 (3)	0.0417 (3)	0.0805 (10)
H29A	0.1726	0.6409	0.0856	0.097*
H29B	0.2697	0.7682	0.0422	0.097*
C31	0.3172 (3)	0.4775 (3)	−0.0222 (3)	0.0763 (10)
H31A	0.2989	0.3866	−0.0245	0.092*
H31B	0.3960	0.5173	−0.0637	0.092*
C30	0.1825 (4)	0.4813 (3)	−0.0686 (3)	0.0924 (12)
H30A	0.1551	0.4369	−0.1430	0.111*
H30B	0.1017	0.4332	−0.0313	0.111*
H22	0.568 (2)	0.6674 (19)	0.4497 (16)	0.030 (5)*
H21	0.395 (3)	0.469 (2)	0.2770 (17)	0.041 (6)*
H6O	−0.073 (3)	0.306 (2)	0.3670 (19)	0.056 (7)*
H5O	0.118 (3)	0.168 (2)	0.441 (2)	0.059 (8)*
H4O	0.417 (3)	0.030 (2)	0.0682 (19)	0.054 (7)*
H1O	−0.031 (3)	0.188 (2)	−0.414 (2)	0.063 (8)*
H2O	0.407 (3)	0.000 (2)	−0.244 (2)	0.053 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0348 (7)	0.0488 (8)	0.0145 (6)	0.0339 (7)	0.0043 (5)	0.0073 (6)
O7	0.0248 (6)	0.0310 (7)	0.0114 (5)	0.0198 (6)	0.0045 (5)	0.0049 (5)
O3	0.0330 (7)	0.0415 (8)	0.0173 (6)	0.0296 (7)	0.0042 (5)	0.0051 (5)
O1	0.0380 (8)	0.0466 (8)	0.0149 (6)	0.0339 (7)	0.0078 (5)	0.0107 (6)
O5	0.0353 (7)	0.0487 (8)	0.0132 (6)	0.0311 (7)	0.0064 (5)	0.0087 (6)
O6	0.0391 (8)	0.0460 (8)	0.0154 (6)	0.0344 (7)	0.0081 (5)	0.0064 (6)
O2	0.0394 (8)	0.0533 (9)	0.0170 (6)	0.0387 (7)	0.0075 (6)	0.0075 (6)
C9	0.0202 (8)	0.0217 (9)	0.0135 (8)	0.0114 (7)	0.0018 (6)	0.0039 (6)
C2	0.0249 (9)	0.0269 (9)	0.0174 (8)	0.0192 (8)	0.0056 (7)	0.0054 (7)
C6	0.0210 (8)	0.0228 (9)	0.0144 (8)	0.0129 (7)	0.0026 (6)	0.0024 (7)
C10	0.0197 (8)	0.0201 (8)	0.0155 (8)	0.0108 (7)	0.0042 (6)	0.0031 (7)
C7	0.0198 (8)	0.0215 (9)	0.0178 (8)	0.0127 (7)	0.0019 (7)	0.0023 (7)
C4	0.0304 (9)	0.0326 (10)	0.0132 (8)	0.0216 (8)	0.0077 (7)	0.0058 (7)
N1	0.0427 (10)	0.0514 (11)	0.0228 (8)	0.0371 (9)	0.0101 (7)	0.0113 (8)
C8	0.0231 (9)	0.0243 (9)	0.0136 (8)	0.0140 (8)	0.0018 (7)	0.0045 (7)
C11	0.0194 (8)	0.0239 (9)	0.0179 (8)	0.0146 (7)	0.0039 (7)	0.0046 (7)
C1	0.0200 (8)	0.0209 (8)	0.0131 (7)	0.0117 (7)	0.0054 (6)	0.0031 (6)
N2	0.0344 (9)	0.0402 (10)	0.0288 (8)	0.0278 (8)	0.0103 (7)	0.0094 (7)
C14	0.0267 (9)	0.0305 (10)	0.0190 (8)	0.0210 (8)	0.0057 (7)	0.0080 (7)
C12	0.0215 (8)	0.0245 (9)	0.0139 (8)	0.0130 (7)	0.0027 (7)	0.0055 (7)
C24	0.0312 (10)	0.0366 (11)	0.0326 (10)	0.0226 (9)	0.0028 (8)	0.0017 (9)
C17	0.0262 (10)	0.0322 (11)	0.0364 (11)	0.0155 (9)	0.0025 (8)	0.0003 (9)
C22	0.0242 (9)	0.0328 (11)	0.0311 (10)	0.0183 (9)	0.0042 (8)	0.0065 (8)
C5	0.0250 (9)	0.0263 (9)	0.0167 (8)	0.0180 (8)	0.0047 (7)	0.0018 (7)
C21	0.0261 (10)	0.0334 (11)	0.0309 (10)	0.0187 (9)	0.0006 (8)	0.0016 (9)
C23	0.0273 (9)	0.0311 (10)	0.0247 (9)	0.0194 (9)	0.0076 (8)	0.0082 (8)
C18	0.0251 (9)	0.0271 (10)	0.0301 (10)	0.0166 (8)	0.0065 (8)	0.0059 (8)
C3	0.0260 (9)	0.0277 (9)	0.0144 (8)	0.0176 (8)	0.0033 (7)	0.0053 (7)
C13	0.0239 (9)	0.0228 (9)	0.0158 (8)	0.0137 (8)	0.0058 (7)	0.0043 (7)
C19	0.0305 (10)	0.0334 (11)	0.0255 (9)	0.0209 (9)	0.0037 (8)	0.0005 (8)
C15	0.0264 (9)	0.0300 (10)	0.0150 (8)	0.0182 (8)	0.0042 (7)	0.0075 (7)
C27	0.0311 (10)	0.0354 (11)	0.0282 (10)	0.0206 (9)	0.0026 (8)	0.0015 (8)
C16	0.0346 (11)	0.0318 (11)	0.0351 (11)	0.0208 (9)	0.0098 (9)	0.0023 (9)
C20	0.0293 (10)	0.0431 (12)	0.0253 (9)	0.0241 (9)	0.0034 (8)	0.0045 (8)
C26	0.0472 (12)	0.0430 (12)	0.0270 (10)	0.0337 (11)	0.0080 (9)	0.0048 (9)
C25	0.0312 (10)	0.0488 (13)	0.0285 (10)	0.0269 (10)	0.0037 (8)	0.0063 (9)
O9	0.0522 (11)	0.0840 (15)	0.0603 (12)	0.0171 (11)	−0.0080 (9)	0.0333 (11)
O8	0.0867 (15)	0.0776 (14)	0.0648 (13)	0.0468 (13)	−0.0015 (11)	0.0304 (11)
C28	0.0556 (17)	0.0592 (19)	0.0606 (18)	0.0020 (15)	0.0081 (14)	0.0004 (15)
C29	0.082 (2)	0.074 (2)	0.095 (3)	0.039 (2)	0.026 (2)	0.023 (2)
C31	0.076 (2)	0.0386 (15)	0.091 (2)	0.0167 (15)	−0.0366 (18)	0.0047 (15)
C30	0.095 (3)	0.059 (2)	0.097 (3)	0.0248 (19)	−0.048 (2)	0.0081 (18)

Geometric parameters (Å, º)

O4—C8	1.3617 (19)	C24—C25	1.379 (3)
O4—H4O	0.87 (3)	C24—C23	1.397 (3)
O7—C1	1.3625 (18)	C24—H24	0.9500
O7—C9	1.3755 (18)	C17—C16	1.379 (3)
O3—C7	1.2650 (19)	C17—C18	1.397 (3)
O1—C3	1.347 (2)	C17—H17	0.9500
O1—H1O	0.97 (3)	C22—C21	1.328 (3)
O5—C12	1.3708 (19)	C22—C23	1.463 (2)
O5—H5O	0.90 (3)	C22—H22	0.97 (2)
O6—C13	1.3538 (19)	C21—C18	1.467 (2)
O6—H6O	0.91 (3)	C21—H21	0.94 (2)
O2—C5	1.3561 (19)	C23—C27	1.395 (3)
O2—H2O	0.86 (3)	C18—C19	1.394 (3)
C9—C8	1.366 (2)	C19—C20	1.374 (2)
C9—C10	1.466 (2)	C19—H19	0.9500
C2—C1	1.382 (2)	C15—H15	0.9500
C2—C3	1.391 (2)	C27—C26	1.382 (3)
C2—H2	0.9500	C27—H27	0.9500
C6—C1	1.396 (2)	C16—H16	0.9500
C6—C5	1.422 (2)	C20—H20	0.9500
C6—C7	1.426 (2)	C26—H26	0.9500
C10—C15	1.399 (2)	C25—H25	0.9500
C10—C11	1.411 (2)	O9—C28	1.390 (3)
C7—C8	1.442 (2)	O9—C31	1.423 (3)
C4—C5	1.373 (2)	O8—C30	1.384 (4)
C4—C3	1.405 (2)	O8—C29	1.438 (4)
C4—H4	0.9500	C28—C29	1.479 (4)
N1—C26	1.336 (3)	C28—H28A	0.9900
N1—C25	1.340 (3)	C28—H28B	0.9900
C11—C12	1.382 (2)	C29—H29A	0.9900
C11—H11	0.9500	C29—H29B	0.9900
N2—C16	1.336 (3)	C31—C30	1.467 (4)
N2—C20	1.342 (2)	C31—H31A	0.9900
C14—C15	1.381 (2)	C31—H31B	0.9900
C14—C13	1.390 (2)	C30—H30A	0.9900
C14—H14	0.9500	C30—H30B	0.9900
C12—C13	1.401 (2)
C8—O4—H4O	107.7 (16)	C24—C23—C22	123.23 (17)
C1—O7—C9	122.44 (12)	C19—C18—C17	116.75 (16)
C3—O1—H1O	113.4 (15)	C19—C18—C21	123.20 (17)
C12—O5—H5O	109.1 (16)	C17—C18—C21	120.04 (17)
C13—O6—H6O	110.1 (16)	O1—C3—C2	122.31 (14)
C5—O2—H2O	104.6 (16)	O1—C3—C4	116.45 (15)
C8—C9—O7	119.29 (14)	C2—C3—C4	121.24 (15)
C8—C9—C10	130.01 (15)	O6—C13—C14	123.78 (15)
O7—C9—C10	110.70 (13)	O6—C13—C12	117.20 (14)
C1—C2—C3	117.83 (14)	C14—C13—C12	119.01 (15)
C1—C2—H2	121.1	C20—C19—C18	119.36 (17)
C3—C2—H2	121.1	C20—C19—H19	120.3
C1—C6—C5	117.40 (14)	C18—C19—H19	120.3
C1—C6—C7	119.67 (14)	C14—C15—C10	121.13 (15)
C5—C6—C7	122.93 (14)	C14—C15—H15	119.4
C15—C10—C11	118.18 (14)	C10—C15—H15	119.4
C15—C10—C9	119.38 (14)	C26—C27—C23	119.60 (18)
C11—C10—C9	122.43 (14)	C26—C27—H27	120.2
O3—C7—C6	122.96 (15)	C23—C27—H27	120.2
O3—C7—C8	119.92 (14)	N2—C16—C17	123.46 (18)
C6—C7—C8	117.09 (14)	N2—C16—H16	118.3
C5—C4—C3	119.74 (15)	C17—C16—H16	118.3
C5—C4—H4	120.1	N2—C20—C19	124.07 (18)
C3—C4—H4	120.1	N2—C20—H20	118.0
C26—N1—C25	116.86 (16)	C19—C20—H20	118.0
O4—C8—C9	121.44 (15)	N1—C26—C27	123.46 (18)
O4—C8—C7	117.31 (14)	N1—C26—H26	118.3
C9—C8—C7	121.24 (14)	C27—C26—H26	118.3
C12—C11—C10	120.42 (14)	N1—C25—C24	123.88 (19)
C12—C11—H11	119.8	N1—C25—H25	118.1
C10—C11—H11	119.8	C24—C25—H25	118.1
O7—C1—C2	116.76 (13)	C28—O9—C31	108.9 (2)
O7—C1—C6	120.13 (14)	C30—O8—C29	110.7 (2)
C2—C1—C6	123.11 (14)	O9—C28—C29	112.0 (2)
C16—N2—C20	116.59 (15)	O9—C28—H28A	109.2
C15—C14—C13	120.57 (15)	C29—C28—H28A	109.2
C15—C14—H14	119.7	O9—C28—H28B	109.2
C13—C14—H14	119.7	C29—C28—H28B	109.2
O5—C12—C11	118.81 (14)	H28A—C28—H28B	107.9
O5—C12—C13	120.51 (14)	O8—C29—C28	110.5 (3)
C11—C12—C13	120.68 (14)	O8—C29—H29A	109.5
C25—C24—C23	119.20 (18)	C28—C29—H29A	109.5
C25—C24—H24	120.4	O8—C29—H29B	109.5
C23—C24—H24	120.4	C28—C29—H29B	109.5
C16—C17—C18	119.77 (18)	H29A—C29—H29B	108.1
C16—C17—H17	120.1	O9—C31—C30	110.7 (3)
C18—C17—H17	120.1	O9—C31—H31A	109.5
C21—C22—C23	125.88 (18)	C30—C31—H31A	109.5
C21—C22—H22	120.1 (12)	O9—C31—H31B	109.5
C23—C22—H22	114.0 (12)	C30—C31—H31B	109.5
O2—C5—C4	119.50 (15)	H31A—C31—H31B	108.1
O2—C5—C6	119.82 (14)	O8—C30—C31	113.3 (3)
C4—C5—C6	120.68 (14)	O8—C30—H30A	108.9
C22—C21—C18	124.69 (19)	C31—C30—H30A	108.9
C22—C21—H21	120.0 (13)	O8—C30—H30B	108.9
C18—C21—H21	115.3 (13)	C31—C30—H30B	108.9
C27—C23—C24	116.99 (16)	H30A—C30—H30B	107.7
C27—C23—C22	119.76 (17)

(QDP_II)

Crystal data

C31H28N2O8	V = 1340.13 (17) Å^3
Mr = 556.55	Z = 2
Triclinic, P1	F(000) = 584
a = 10.0381 (7) Å	Dx = 1.379 Mg m^−3
b = 11.5707 (8) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.0194 (9) Å	µ = 0.10 mm^−1
α = 76.744 (5)°	T = 293 K
β = 84.502 (6)°	Plate, yellow
γ = 65.573 (5)°	0.40 × 0.20 × 0.20 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.034
Tmin = 0.794, Tmax = 1.000	θmax = 27.5°, θmin = 3.0°
14382 measured reflections	h = −13→12
6106 independent reflections	k = −15→15
4337 reflections with I > 2σ(I)	l = −16→16

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) = 0.162	w = 1/[σ^2(Fo^2) + (0.0802P)^2 + 0.6053P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
6106 reflections	Δρmax = 0.48 e Å^−3
398 parameters	Δρmin = −0.48 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
O4	0.20231 (15)	0.44770 (15)	0.59077 (11)	0.0257 (3)
O3	0.09228 (14)	0.49729 (15)	0.39653 (11)	0.0248 (3)
H21	1.405 (3)	0.165 (2)	0.0558 (19)	0.030 (6)*
H22	1.420 (3)	−0.042 (3)	0.224 (2)	0.049 (8)*
H5O	0.556 (3)	0.328 (3)	0.941 (2)	0.055 (9)*
H1O	0.708 (4)	0.315 (3)	0.089 (2)	0.059 (9)*
H2O	0.094 (3)	0.497 (3)	0.257 (2)	0.055 (9)*
H6O	0.874 (3)	0.202 (3)	0.867 (2)	0.040 (7)*
H4O	0.116 (3)	0.475 (3)	0.566 (2)	0.055 (9)*
O7	0.53200 (14)	0.34737 (13)	0.43400 (10)	0.0185 (3)
O1	0.61708 (16)	0.34008 (15)	0.07185 (11)	0.0256 (4)
O5	0.48500 (15)	0.33911 (15)	0.89707 (11)	0.0258 (3)
C9	0.4428 (2)	0.37189 (18)	0.52011 (14)	0.0163 (4)
O2	0.13312 (15)	0.48916 (16)	0.19586 (11)	0.0283 (4)
C6	0.3272 (2)	0.42022 (18)	0.31970 (14)	0.0173 (4)
C2	0.5793 (2)	0.34111 (19)	0.25600 (15)	0.0201 (4)
H2	0.6792	0.3071	0.2692	0.024*
O6	0.78169 (16)	0.23014 (15)	0.88426 (11)	0.0251 (3)
C7	0.2294 (2)	0.45003 (19)	0.40601 (14)	0.0178 (4)
C8	0.2946 (2)	0.42239 (19)	0.50779 (14)	0.0177 (4)
C10	0.5295 (2)	0.33630 (18)	0.61556 (14)	0.0163 (4)
C11	0.4657 (2)	0.35691 (18)	0.71409 (14)	0.0179 (4)
H11	0.3644	0.3961	0.7200	0.021*
C4	0.3766 (2)	0.4141 (2)	0.13466 (15)	0.0209 (4)
H4	0.3440	0.4283	0.0666	0.025*
C1	0.4784 (2)	0.36986 (18)	0.33607 (14)	0.0167 (4)
C3	0.5270 (2)	0.36451 (19)	0.15524 (15)	0.0195 (4)
C14	0.7684 (2)	0.24251 (19)	0.69748 (15)	0.0203 (4)
H14	0.8697	0.2040	0.6917	0.024*
C5	0.2781 (2)	0.44150 (19)	0.21555 (15)	0.0196 (4)
C12	0.5518 (2)	0.31958 (19)	0.80244 (14)	0.0180 (4)
C13	0.7047 (2)	0.26253 (19)	0.79474 (14)	0.0180 (4)
C15	0.6828 (2)	0.27924 (19)	0.60900 (14)	0.0191 (4)
H15	0.7273	0.2660	0.5442	0.023*
N2	0.90039 (19)	0.25732 (19)	0.11058 (14)	0.0301 (4)
N1	1.92605 (18)	−0.13443 (18)	0.14926 (14)	0.0273 (4)
C22	1.4598 (2)	0.0103 (2)	0.17171 (18)	0.0277 (5)
C17	1.1308 (2)	0.1016 (2)	0.18489 (18)	0.0313 (5)
H17	1.1816	0.0270	0.2344	0.038*
C18	1.2062 (2)	0.1645 (2)	0.11545 (17)	0.0254 (5)
C23	1.6196 (2)	−0.0365 (2)	0.16335 (17)	0.0242 (4)
C24	1.7088 (2)	−0.1457 (2)	0.23461 (18)	0.0290 (5)
H24	1.6673	−0.1881	0.2887	0.035*
C21	1.3661 (2)	0.1171 (2)	0.11180 (19)	0.0275 (5)
C27	1.6897 (2)	0.0225 (2)	0.08549 (17)	0.0279 (5)
H27	1.6353	0.0960	0.0363	0.033*
C19	1.1222 (2)	0.2763 (2)	0.04449 (17)	0.0289 (5)
H19	1.1670	0.3226	−0.0029	0.035*
C20	0.9724 (2)	0.3181 (2)	0.04478 (17)	0.0320 (5)
H20	0.9184	0.3927	−0.0036	0.038*
C26	1.8403 (2)	−0.0288 (2)	0.08176 (17)	0.0301 (5)
H26	1.8850	0.0123	0.0292	0.036*
C25	1.8595 (2)	−0.1906 (2)	0.22449 (18)	0.0293 (5)
H25	1.9170	−0.2637	0.2727	0.035*
C16	0.9807 (2)	0.1507 (2)	0.17970 (18)	0.0326 (5)
H16	0.9324	0.1074	0.2268	0.039*
O8	0.9212 (3)	0.9114 (3)	0.4308 (2)	0.1020 (10)
C29	0.7547 (5)	0.8597 (4)	0.5466 (3)	0.0880 (13)
H29A	0.7033	0.8232	0.5132	0.106*
H29B	0.7449	0.8369	0.6225	0.106*
C28	0.9102 (5)	0.8140 (4)	0.5149 (3)	0.0865 (12)
H28A	0.9711	0.8011	0.5735	0.104*
H28B	0.9413	0.7324	0.4922	0.104*
C31	0.7966 (6)	1.0237 (3)	0.4287 (4)	0.1018 (17)
H31A	0.7496	1.0513	0.3604	0.122*
H31B	0.8224	1.0922	0.4394	0.122*
C30	0.6989 (5)	1.0016 (4)	0.5091 (5)	0.1097 (18)
H30A	0.6006	1.0357	0.4813	0.132*
H30B	0.6968	1.0433	0.5663	0.132*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0122 (7)	0.0459 (9)	0.0146 (7)	−0.0065 (7)	0.0016 (5)	−0.0084 (6)
O3	0.0128 (7)	0.0393 (9)	0.0168 (7)	−0.0059 (6)	0.0003 (5)	−0.0045 (6)
O7	0.0138 (6)	0.0282 (7)	0.0112 (6)	−0.0055 (6)	0.0005 (5)	−0.0057 (5)
O1	0.0140 (7)	0.0446 (9)	0.0136 (7)	−0.0048 (7)	0.0009 (5)	−0.0112 (6)
O5	0.0174 (7)	0.0455 (9)	0.0129 (7)	−0.0095 (7)	0.0007 (6)	−0.0099 (6)
C9	0.0162 (9)	0.0203 (9)	0.0121 (8)	−0.0068 (8)	0.0021 (7)	−0.0046 (7)
O2	0.0135 (7)	0.0491 (10)	0.0161 (7)	−0.0056 (7)	−0.0010 (6)	−0.0081 (7)
C6	0.0146 (9)	0.0206 (10)	0.0144 (9)	−0.0046 (8)	−0.0012 (7)	−0.0032 (7)
C2	0.0119 (9)	0.0271 (11)	0.0174 (9)	−0.0031 (8)	−0.0009 (7)	−0.0063 (8)
O6	0.0145 (7)	0.0405 (9)	0.0147 (7)	−0.0048 (7)	−0.0023 (5)	−0.0065 (6)
C7	0.0138 (9)	0.0223 (10)	0.0156 (9)	−0.0065 (8)	−0.0003 (7)	−0.0019 (7)
C8	0.0158 (9)	0.0218 (10)	0.0136 (9)	−0.0061 (8)	0.0022 (7)	−0.0038 (7)
C10	0.0157 (9)	0.0181 (9)	0.0150 (9)	−0.0068 (8)	0.0000 (7)	−0.0030 (7)
C11	0.0143 (9)	0.0218 (10)	0.0162 (9)	−0.0058 (8)	−0.0004 (7)	−0.0043 (7)
C4	0.0189 (10)	0.0298 (11)	0.0125 (9)	−0.0074 (9)	−0.0032 (7)	−0.0049 (8)
C1	0.0167 (9)	0.0192 (9)	0.0131 (9)	−0.0059 (8)	−0.0018 (7)	−0.0032 (7)
C3	0.0166 (9)	0.0248 (10)	0.0145 (9)	−0.0052 (8)	0.0014 (7)	−0.0061 (8)
C14	0.0131 (9)	0.0265 (10)	0.0182 (9)	−0.0048 (8)	0.0002 (7)	−0.0050 (8)
C5	0.0148 (9)	0.0236 (10)	0.0178 (9)	−0.0046 (8)	−0.0029 (7)	−0.0045 (8)
C12	0.0183 (9)	0.0230 (10)	0.0125 (9)	−0.0079 (8)	0.0019 (7)	−0.0050 (7)
C13	0.0172 (9)	0.0222 (10)	0.0133 (9)	−0.0066 (8)	−0.0032 (7)	−0.0022 (7)
C15	0.0171 (9)	0.0248 (10)	0.0128 (9)	−0.0055 (8)	0.0014 (7)	−0.0054 (7)
N2	0.0168 (8)	0.0459 (12)	0.0224 (9)	−0.0049 (8)	−0.0020 (7)	−0.0115 (8)
N1	0.0160 (8)	0.0340 (10)	0.0284 (9)	−0.0051 (8)	−0.0036 (7)	−0.0082 (8)
C22	0.0176 (10)	0.0273 (11)	0.0352 (12)	−0.0071 (9)	0.0003 (9)	−0.0049 (9)
C17	0.0206 (10)	0.0312 (12)	0.0351 (12)	−0.0065 (9)	−0.0029 (9)	−0.0002 (10)
C18	0.0171 (10)	0.0276 (11)	0.0295 (11)	−0.0050 (9)	−0.0007 (8)	−0.0093 (9)
C23	0.0169 (10)	0.0238 (11)	0.0296 (11)	−0.0055 (8)	−0.0035 (8)	−0.0054 (9)
C24	0.0213 (10)	0.0270 (11)	0.0356 (12)	−0.0093 (9)	−0.0043 (9)	0.0002 (9)
C21	0.0190 (10)	0.0272 (11)	0.0352 (12)	−0.0091 (9)	−0.0002 (9)	−0.0052 (9)
C27	0.0183 (10)	0.0321 (12)	0.0272 (11)	−0.0068 (9)	−0.0040 (8)	0.0001 (9)
C19	0.0219 (10)	0.0315 (12)	0.0290 (11)	−0.0079 (9)	−0.0022 (9)	−0.0031 (9)
C20	0.0225 (11)	0.0380 (13)	0.0264 (11)	−0.0027 (10)	−0.0045 (9)	−0.0059 (10)
C26	0.0190 (10)	0.0431 (13)	0.0249 (11)	−0.0117 (10)	0.0006 (8)	−0.0029 (10)
C25	0.0202 (10)	0.0271 (11)	0.0353 (12)	−0.0054 (9)	−0.0063 (9)	−0.0021 (9)
C16	0.0201 (10)	0.0461 (14)	0.0299 (12)	−0.0127 (10)	0.0020 (9)	−0.0070 (10)
O8	0.111 (2)	0.0655 (17)	0.108 (2)	−0.0251 (17)	0.0533 (19)	−0.0217 (16)
C29	0.128 (4)	0.064 (2)	0.093 (3)	−0.060 (3)	0.040 (3)	−0.030 (2)
C28	0.099 (3)	0.054 (2)	0.084 (3)	−0.015 (2)	0.003 (2)	−0.006 (2)
C31	0.136 (4)	0.039 (2)	0.105 (3)	−0.021 (2)	0.053 (3)	−0.015 (2)
C30	0.089 (3)	0.057 (2)	0.184 (5)	−0.035 (2)	0.056 (3)	−0.039 (3)

Geometric parameters (Å, º)

O4—C8	1.356 (2)	N1—C25	1.331 (3)
O4—H4O	0.86 (3)	N1—C26	1.337 (3)
O3—C7	1.260 (2)	C22—C21	1.325 (3)
O7—C1	1.359 (2)	C22—C23	1.468 (3)
O7—C9	1.372 (2)	C22—H22	0.97 (3)
O1—C3	1.348 (2)	C17—C16	1.375 (3)
O1—H1O	0.87 (3)	C17—C18	1.394 (3)
O5—C12	1.365 (2)	C17—H17	0.9300
O5—H5O	0.91 (3)	C18—C19	1.392 (3)
C9—C8	1.366 (3)	C18—C21	1.466 (3)
C9—C10	1.465 (3)	C23—C27	1.389 (3)
O2—C5	1.353 (2)	C23—C24	1.394 (3)
O2—H2O	0.87 (3)	C24—C25	1.385 (3)
C6—C1	1.401 (3)	C24—H24	0.9300
C6—C5	1.420 (3)	C21—H21	0.96 (2)
C6—C7	1.426 (3)	C27—C26	1.378 (3)
C2—C1	1.379 (3)	C27—H27	0.9300
C2—C3	1.386 (3)	C19—C20	1.376 (3)
C2—H2	0.9300	C19—H19	0.9300
O6—C13	1.353 (2)	C20—H20	0.9300
O6—H6O	0.87 (3)	C26—H26	0.9300
C7—C8	1.444 (3)	C25—H25	0.9300
C10—C11	1.403 (3)	C16—H16	0.9300
C10—C15	1.404 (3)	O8—C31	1.379 (5)
C11—C12	1.383 (3)	O8—C28	1.413 (4)
C11—H11	0.9300	C29—C30	1.473 (5)
C4—C5	1.372 (3)	C29—C28	1.476 (6)
C4—C3	1.404 (3)	C29—H29A	0.9700
C4—H4	0.9300	C29—H29B	0.9700
C14—C15	1.382 (3)	C28—H28A	0.9700
C14—C13	1.387 (3)	C28—H28B	0.9700
C14—H14	0.9300	C31—C30	1.419 (5)
C12—C13	1.401 (3)	C31—H31A	0.9700
C15—H15	0.9300	C31—H31B	0.9700
N2—C20	1.332 (3)	C30—H30A	0.9700
N2—C16	1.337 (3)	C30—H30B	0.9700
C8—O4—H4O	106 (2)	C16—C17—H17	120.2
C1—O7—C9	122.39 (14)	C18—C17—H17	120.2
C3—O1—H1O	111 (2)	C19—C18—C17	116.72 (19)
C12—O5—H5O	106.4 (19)	C19—C18—C21	119.6 (2)
C8—C9—O7	119.43 (16)	C17—C18—C21	123.7 (2)
C8—C9—C10	129.77 (17)	C27—C23—C24	116.81 (19)
O7—C9—C10	110.80 (15)	C27—C23—C22	122.98 (19)
C5—O2—H2O	103 (2)	C24—C23—C22	120.20 (19)
C1—C6—C5	117.57 (17)	C25—C24—C23	119.7 (2)
C1—C6—C7	119.68 (16)	C25—C24—H24	120.2
C5—C6—C7	122.74 (16)	C23—C24—H24	120.2
C1—C2—C3	117.81 (17)	C22—C21—C18	126.2 (2)
C1—C2—H2	121.1	C22—C21—H21	117.9 (14)
C3—C2—H2	121.1	C18—C21—H21	115.6 (14)
C13—O6—H6O	107.2 (17)	C26—C27—C23	119.5 (2)
O3—C7—C6	122.97 (17)	C26—C27—H27	120.3
O3—C7—C8	120.25 (17)	C23—C27—H27	120.3
C6—C7—C8	116.78 (16)	C20—C19—C18	119.7 (2)
O4—C8—C9	121.43 (17)	C20—C19—H19	120.2
O4—C8—C7	117.14 (16)	C18—C19—H19	120.2
C9—C8—C7	121.43 (17)	N2—C20—C19	123.6 (2)
C11—C10—C15	118.19 (17)	N2—C20—H20	118.2
C11—C10—C9	122.70 (16)	C19—C20—H20	118.2
C15—C10—C9	119.11 (16)	N1—C26—C27	123.8 (2)
C12—C11—C10	120.68 (17)	N1—C26—H26	118.1
C12—C11—H11	119.7	C27—C26—H26	118.1
C10—C11—H11	119.7	N1—C25—C24	123.3 (2)
C5—C4—C3	119.63 (17)	N1—C25—H25	118.3
C5—C4—H4	120.2	C24—C25—H25	118.3
C3—C4—H4	120.2	N2—C16—C17	123.6 (2)
O7—C1—C2	116.84 (16)	N2—C16—H16	118.2
O7—C1—C6	120.28 (16)	C17—C16—H16	118.2
C2—C1—C6	122.87 (17)	C31—O8—C28	108.9 (3)
O1—C3—C2	122.15 (17)	C30—C29—C28	103.5 (3)
O1—C3—C4	116.23 (17)	C30—C29—H29A	111.1
C2—C3—C4	121.61 (17)	C28—C29—H29A	111.1
C15—C14—C13	120.65 (17)	C30—C29—H29B	111.1
C15—C14—H14	119.7	C28—C29—H29B	111.1
C13—C14—H14	119.7	H29A—C29—H29B	109.0
O2—C5—C4	119.70 (17)	O8—C28—C29	106.4 (3)
O2—C5—C6	119.80 (17)	O8—C28—H28A	110.4
C4—C5—C6	120.51 (17)	C29—C28—H28A	110.4
O5—C12—C11	118.68 (17)	O8—C28—H28B	110.4
O5—C12—C13	120.82 (16)	C29—C28—H28B	110.4
C11—C12—C13	120.49 (17)	H28A—C28—H28B	108.6
O6—C13—C14	123.79 (17)	O8—C31—C30	109.8 (3)
O6—C13—C12	117.13 (16)	O8—C31—H31A	109.7
C14—C13—C12	119.09 (17)	C30—C31—H31A	109.7
C14—C15—C10	120.90 (17)	O8—C31—H31B	109.7
C14—C15—H15	119.6	C30—C31—H31B	109.7
C10—C15—H15	119.6	H31A—C31—H31B	108.2
C20—N2—C16	116.91 (18)	C31—C30—C29	106.0 (3)
C25—N1—C26	116.90 (18)	C31—C30—H30A	110.5
C21—C22—C23	124.7 (2)	C29—C30—H30A	110.5
C21—C22—H22	117.8 (16)	C31—C30—H30B	110.5
C23—C22—H22	117.5 (16)	C29—C30—H30B	110.5
C16—C17—C18	119.6 (2)	H30A—C30—H30B	108.7

(QDP_III)

Crystal data

C30H26N3O8	V = 1322.2 (4) Å^3
Mr = 556.54	Z = 2
Triclinic, P1	F(000) = 582
a = 9.9867 (15) Å	Dx = 1.398 Mg m^−3
b = 11.2949 (17) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.040 (2) Å	µ = 0.10 mm^−1
α = 79.558 (6)°	T = 150 K
β = 85.192 (6)°	Plate, yellow
γ = 66.082 (5)°	0.40 × 0.20 × 0.12 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.052
Tmin = 0.747, Tmax = 1.000	θmax = 27.5°, θmin = 3.0°
13781 measured reflections	h = −12→12
6040 independent reflections	k = −14→14
3745 reflections with I > 2σ(I)	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.178	w = 1/[σ^2(Fo^2) + (0.0779P)^2 + 0.8181P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
6040 reflections	Δρmax = 0.49 e Å^−3
400 parameters	Δρmin = −0.41 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
H21	−0.410 (3)	0.325 (3)	0.441 (2)	0.023 (7)*
H22	−0.421 (3)	0.540 (3)	0.281 (2)	0.036 (9)*
H4O	0.884 (4)	0.026 (3)	−0.068 (2)	0.037 (9)*
H1O	0.291 (4)	0.182 (4)	0.414 (3)	0.052 (11)*
H5O	0.443 (4)	0.171 (3)	−0.438 (3)	0.051 (11)*
H6O	0.109 (5)	0.314 (4)	−0.369 (3)	0.087 (14)*
H2O	0.916 (4)	−0.019 (4)	0.240 (3)	0.064 (12)*
O7	0.46781 (17)	0.15568 (18)	0.06622 (12)	0.0198 (4)
O4	0.7980 (2)	0.0549 (2)	−0.09157 (14)	0.0268 (5)
O3	0.90774 (18)	−0.00632 (19)	0.10269 (13)	0.0247 (4)
O1	0.3810 (2)	0.15848 (19)	0.42803 (13)	0.0233 (4)
O5	0.5140 (2)	0.16261 (19)	−0.39543 (13)	0.0241 (4)
O2	0.86627 (19)	−0.0022 (2)	0.30414 (14)	0.0268 (5)
O6	0.2176 (2)	0.28080 (19)	−0.38114 (13)	0.0241 (4)
C2	0.4191 (3)	0.1614 (3)	0.24381 (19)	0.0212 (6)
H2	0.3170	0.2001	0.2302	0.025*
C9	0.5576 (3)	0.1322 (3)	−0.02008 (18)	0.0178 (5)
C6	0.6720 (3)	0.0745 (3)	0.18020 (18)	0.0180 (5)
C7	0.7699 (3)	0.0449 (3)	0.09392 (18)	0.0184 (5)
C8	0.7053 (3)	0.0780 (3)	−0.00765 (18)	0.0193 (5)
C4	0.6217 (3)	0.0789 (3)	0.36537 (19)	0.0204 (6)
H4	0.6549	0.0617	0.4348	0.025*
C1	0.5211 (3)	0.1304 (2)	0.16420 (18)	0.0175 (5)
C10	0.4701 (3)	0.1720 (2)	−0.11489 (18)	0.0175 (5)
C11	0.5339 (3)	0.1470 (3)	−0.21332 (18)	0.0185 (5)
H11	0.6372	0.1031	−0.2196	0.022*
C14	0.2324 (3)	0.2730 (3)	−0.19569 (19)	0.0224 (6)
H14	0.1291	0.3166	−0.1895	0.027*
C13	0.2954 (3)	0.2477 (3)	−0.29248 (19)	0.0183 (5)
C3	0.4713 (3)	0.1340 (3)	0.34477 (18)	0.0190 (5)
C12	0.4479 (3)	0.1856 (3)	−0.30095 (18)	0.0181 (5)
C5	0.7208 (3)	0.0501 (3)	0.28455 (19)	0.0189 (5)
C15	0.3181 (3)	0.2355 (3)	−0.10817 (19)	0.0210 (6)
H15	0.2728	0.2532	−0.0425	0.025*
N1	0.0991 (2)	0.2330 (2)	0.39415 (17)	0.0274 (5)
N2	−0.9263 (2)	0.6276 (2)	0.34570 (18)	0.0271 (5)
C18	−0.2072 (3)	0.3292 (3)	0.3879 (2)	0.0231 (6)
C22	−0.4594 (3)	0.4847 (3)	0.3317 (2)	0.0252 (6)
C21	−0.3676 (3)	0.3782 (3)	0.3910 (2)	0.0260 (6)
C23	−0.6192 (3)	0.5318 (3)	0.3373 (2)	0.0243 (6)
C24	−0.7058 (3)	0.6358 (3)	0.2639 (2)	0.0291 (7)
H24	−0.6614	0.6759	0.2092	0.035*
C19	−0.1259 (3)	0.2216 (3)	0.4607 (2)	0.0275 (6)
H19	−0.1743	0.1787	0.5097	0.033*
C27	−0.6924 (3)	0.4769 (3)	0.4140 (2)	0.0271 (6)
H27	−0.6386	0.4055	0.4654	0.032*
C17	−0.1288 (3)	0.3857 (3)	0.3170 (2)	0.0273 (6)
H17	−0.1788	0.4585	0.2653	0.033*
C26	−0.8425 (3)	0.5264 (3)	0.4149 (2)	0.0278 (6)
H26	−0.8899	0.4867	0.4676	0.033*
C20	0.0249 (3)	0.1773 (3)	0.4615 (2)	0.0287 (7)
H20	0.0780	0.1043	0.5120	0.034*
C25	−0.8567 (3)	0.6801 (3)	0.2716 (2)	0.0295 (7)
H25	−0.9138	0.7517	0.2216	0.035*
C16	0.0210 (3)	0.3355 (3)	0.3225 (2)	0.0279 (6)
H16	0.0725	0.3749	0.2732	0.033*
N3	0.8016 (4)	0.4054 (3)	0.0184 (2)	0.0511 (8)
C29	0.9415 (4)	0.2947 (4)	0.0374 (4)	0.0644 (11)
H29A	0.9531	0.2320	−0.0092	0.097*
H29B	0.9449	0.2515	0.1100	0.097*
H29C	1.0208	0.3256	0.0242	0.097*
O8	0.8856 (5)	0.5211 (4)	−0.1113 (3)	0.1013 (12)
C30	0.6750 (5)	0.3998 (5)	0.0766 (3)	0.0683 (12)
H30A	0.5964	0.4879	0.0698	0.102*
H30B	0.7004	0.3668	0.1502	0.102*
H30C	0.6420	0.3409	0.0494	0.102*
C28	0.7850 (5)	0.5093 (4)	−0.0565 (3)	0.0621 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0135 (8)	0.0315 (11)	0.0108 (8)	−0.0054 (8)	0.0000 (6)	−0.0034 (7)
O4	0.0109 (9)	0.0487 (13)	0.0144 (9)	−0.0056 (9)	0.0009 (7)	−0.0052 (8)
O3	0.0139 (9)	0.0381 (12)	0.0170 (9)	−0.0058 (8)	0.0007 (7)	−0.0031 (8)
O1	0.0130 (9)	0.0405 (12)	0.0125 (9)	−0.0053 (9)	0.0024 (7)	−0.0088 (8)
O5	0.0169 (9)	0.0415 (12)	0.0120 (9)	−0.0085 (9)	0.0009 (7)	−0.0078 (8)
O2	0.0127 (9)	0.0446 (13)	0.0171 (9)	−0.0054 (9)	−0.0020 (7)	−0.0040 (9)
O6	0.0151 (9)	0.0381 (12)	0.0141 (9)	−0.0053 (8)	−0.0046 (7)	−0.0029 (8)
C2	0.0134 (12)	0.0300 (15)	0.0170 (12)	−0.0045 (11)	−0.0010 (10)	−0.0055 (11)
C9	0.0169 (12)	0.0231 (14)	0.0133 (12)	−0.0073 (11)	0.0015 (9)	−0.0047 (10)
C6	0.0160 (12)	0.0232 (14)	0.0143 (12)	−0.0070 (11)	0.0000 (9)	−0.0041 (10)
C7	0.0161 (12)	0.0226 (14)	0.0145 (12)	−0.0063 (11)	−0.0010 (9)	−0.0011 (10)
C8	0.0163 (12)	0.0269 (14)	0.0121 (12)	−0.0064 (11)	0.0028 (9)	−0.0034 (10)
C4	0.0194 (13)	0.0265 (15)	0.0136 (12)	−0.0067 (11)	−0.0022 (10)	−0.0037 (10)
C1	0.0158 (12)	0.0224 (14)	0.0119 (11)	−0.0053 (11)	−0.0030 (9)	−0.0008 (10)
C10	0.0151 (12)	0.0222 (14)	0.0133 (12)	−0.0064 (11)	−0.0013 (9)	−0.0002 (10)
C11	0.0135 (12)	0.0253 (14)	0.0167 (12)	−0.0075 (11)	0.0017 (9)	−0.0047 (10)
C14	0.0134 (12)	0.0314 (16)	0.0193 (13)	−0.0059 (11)	−0.0008 (10)	−0.0037 (11)
C13	0.0153 (12)	0.0242 (14)	0.0147 (12)	−0.0072 (11)	−0.0042 (9)	−0.0008 (10)
C3	0.0168 (12)	0.0264 (14)	0.0130 (12)	−0.0082 (11)	0.0020 (9)	−0.0032 (10)
C12	0.0176 (12)	0.0235 (14)	0.0123 (12)	−0.0074 (11)	0.0018 (9)	−0.0038 (10)
C5	0.0145 (12)	0.0242 (14)	0.0165 (12)	−0.0061 (11)	−0.0019 (9)	−0.0027 (10)
C15	0.0173 (12)	0.0291 (15)	0.0140 (12)	−0.0058 (11)	0.0012 (10)	−0.0060 (11)
N1	0.0193 (11)	0.0395 (15)	0.0206 (12)	−0.0077 (11)	−0.0017 (9)	−0.0072 (10)
N2	0.0181 (11)	0.0342 (14)	0.0252 (12)	−0.0054 (10)	−0.0016 (9)	−0.0069 (10)
C18	0.0161 (13)	0.0266 (15)	0.0256 (14)	−0.0062 (11)	−0.0018 (10)	−0.0069 (11)
C22	0.0196 (13)	0.0270 (15)	0.0280 (15)	−0.0087 (12)	0.0005 (11)	−0.0037 (12)
C21	0.0175 (13)	0.0286 (16)	0.0307 (15)	−0.0083 (12)	−0.0007 (11)	−0.0038 (12)
C23	0.0179 (13)	0.0237 (15)	0.0299 (15)	−0.0058 (11)	−0.0023 (11)	−0.0060 (12)
C24	0.0206 (14)	0.0303 (16)	0.0326 (16)	−0.0090 (12)	−0.0026 (11)	0.0023 (13)
C19	0.0222 (14)	0.0321 (16)	0.0250 (14)	−0.0086 (12)	−0.0005 (11)	−0.0020 (12)
C27	0.0189 (13)	0.0302 (16)	0.0277 (15)	−0.0059 (12)	−0.0028 (11)	−0.0020 (12)
C17	0.0191 (13)	0.0300 (16)	0.0276 (15)	−0.0057 (12)	−0.0025 (11)	−0.0007 (12)
C26	0.0205 (13)	0.0380 (17)	0.0225 (14)	−0.0106 (13)	−0.0002 (11)	−0.0014 (12)
C20	0.0213 (14)	0.0339 (17)	0.0222 (14)	−0.0025 (13)	−0.0024 (11)	−0.0022 (12)
C25	0.0196 (14)	0.0308 (16)	0.0317 (16)	−0.0039 (12)	−0.0052 (12)	−0.0016 (13)
C16	0.0202 (13)	0.0379 (17)	0.0246 (14)	−0.0116 (13)	0.0020 (11)	−0.0038 (12)
N3	0.067 (2)	0.0468 (18)	0.0438 (17)	−0.0253 (17)	0.0084 (15)	−0.0152 (15)
C29	0.058 (3)	0.049 (2)	0.082 (3)	−0.016 (2)	0.010 (2)	−0.018 (2)
O8	0.137 (3)	0.121 (3)	0.073 (2)	−0.085 (3)	0.011 (2)	−0.006 (2)
C30	0.086 (3)	0.076 (3)	0.060 (3)	−0.048 (3)	0.012 (2)	−0.020 (2)
C28	0.100 (3)	0.061 (3)	0.040 (2)	−0.049 (3)	0.012 (2)	−0.0095 (19)

Geometric parameters (Å, º)

O7—C1	1.362 (3)	N1—C16	1.349 (4)
O7—C9	1.374 (3)	N2—C25	1.335 (4)
O4—C8	1.364 (3)	N2—C26	1.341 (4)
O4—H4O	0.85 (3)	C18—C17	1.395 (4)
O3—C7	1.265 (3)	C18—C19	1.395 (4)
O1—C3	1.346 (3)	C18—C21	1.467 (4)
O1—H1O	0.86 (4)	C22—C21	1.331 (4)
O5—C12	1.365 (3)	C22—C23	1.464 (4)
O5—H5O	0.90 (4)	C22—H22	0.99 (3)
O2—C5	1.355 (3)	C21—H21	0.99 (3)
O2—H2O	0.94 (4)	C23—C27	1.392 (4)
O6—C13	1.356 (3)	C23—C24	1.396 (4)
O6—H6O	1.01 (4)	C24—C25	1.383 (4)
C2—C1	1.379 (3)	C24—H24	0.9500
C2—C3	1.392 (3)	C19—C20	1.381 (4)
C2—H2	0.9500	C19—H19	0.9500
C9—C8	1.360 (3)	C27—C26	1.371 (4)
C9—C10	1.468 (3)	C27—H27	0.9500
C6—C1	1.396 (3)	C17—C16	1.371 (4)
C6—C7	1.421 (3)	C17—H17	0.9500
C6—C5	1.425 (3)	C26—H26	0.9500
C7—C8	1.442 (3)	C20—H20	0.9500
C4—C5	1.373 (3)	C25—H25	0.9500
C4—C3	1.402 (3)	C16—H16	0.9500
C4—H4	0.9500	N3—C28	1.346 (5)
C10—C15	1.394 (3)	N3—C30	1.436 (5)
C10—C11	1.408 (3)	N3—C29	1.452 (5)
C11—C12	1.384 (3)	C29—H29A	0.9800
C11—H11	0.9500	C29—H29B	0.9800
C14—C15	1.382 (3)	C29—H29C	0.9800
C14—C13	1.386 (3)	O8—C28	1.221 (5)
C14—H14	0.9500	C30—H30A	0.9800
C13—C12	1.399 (3)	C30—H30B	0.9800
C15—H15	0.9500	C30—H30C	0.9800
N1—C20	1.336 (4)
C1—O7—C9	122.44 (18)	C17—C18—C19	116.9 (2)
C8—O4—H4O	106 (2)	C17—C18—C21	123.8 (2)
C3—O1—H1O	114 (2)	C19—C18—C21	119.3 (3)
C12—O5—H5O	106 (2)	C21—C22—C23	124.7 (3)
C5—O2—H2O	107 (2)	C21—C22—H22	120.2 (18)
C13—O6—H6O	114 (2)	C23—C22—H22	115.0 (18)
C1—C2—C3	117.5 (2)	C22—C21—C18	126.0 (3)
C1—C2—H2	121.2	C22—C21—H21	117.6 (16)
C3—C2—H2	121.2	C18—C21—H21	116.4 (16)
C8—C9—O7	119.2 (2)	C27—C23—C24	116.8 (2)
C8—C9—C10	130.4 (2)	C27—C23—C22	122.8 (2)
O7—C9—C10	110.42 (19)	C24—C23—C22	120.4 (3)
C1—C6—C7	119.8 (2)	C25—C24—C23	119.4 (3)
C1—C6—C5	117.4 (2)	C25—C24—H24	120.3
C7—C6—C5	122.8 (2)	C23—C24—H24	120.3
O3—C7—C6	123.2 (2)	C20—C19—C18	120.1 (3)
O3—C7—C8	119.9 (2)	C20—C19—H19	120.0
C6—C7—C8	116.9 (2)	C18—C19—H19	120.0
C9—C8—O4	120.9 (2)	C26—C27—C23	119.7 (3)
C9—C8—C7	121.6 (2)	C26—C27—H27	120.1
O4—C8—C7	117.5 (2)	C23—C27—H27	120.1
C5—C4—C3	119.6 (2)	C16—C17—C18	119.5 (3)
C5—C4—H4	120.2	C16—C17—H17	120.3
C3—C4—H4	120.2	C18—C17—H17	120.3
O7—C1—C2	116.7 (2)	N2—C26—C27	123.7 (3)
O7—C1—C6	120.0 (2)	N2—C26—H26	118.1
C2—C1—C6	123.3 (2)	C27—C26—H26	118.1
C15—C10—C11	118.2 (2)	N1—C20—C19	122.7 (3)
C15—C10—C9	119.5 (2)	N1—C20—H20	118.7
C11—C10—C9	122.4 (2)	C19—C20—H20	118.7
C12—C11—C10	120.7 (2)	N2—C25—C24	123.4 (3)
C12—C11—H11	119.6	N2—C25—H25	118.3
C10—C11—H11	119.6	C24—C25—H25	118.3
C15—C14—C13	120.8 (2)	N1—C16—C17	123.4 (3)
C15—C14—H14	119.6	N1—C16—H16	118.3
C13—C14—H14	119.6	C17—C16—H16	118.3
O6—C13—C14	123.8 (2)	C28—N3—C30	119.0 (4)
O6—C13—C12	117.2 (2)	C28—N3—C29	122.1 (4)
C14—C13—C12	119.0 (2)	C30—N3—C29	118.8 (3)
O1—C3—C2	122.2 (2)	N3—C29—H29A	109.5
O1—C3—C4	116.2 (2)	N3—C29—H29B	109.5
C2—C3—C4	121.6 (2)	H29A—C29—H29B	109.5
O5—C12—C11	119.0 (2)	N3—C29—H29C	109.5
O5—C12—C13	120.7 (2)	H29A—C29—H29C	109.5
C11—C12—C13	120.3 (2)	H29B—C29—H29C	109.5
O2—C5—C4	119.7 (2)	N3—C30—H30A	109.5
O2—C5—C6	119.7 (2)	N3—C30—H30B	109.5
C4—C5—C6	120.5 (2)	H30A—C30—H30B	109.5
C14—C15—C10	121.0 (2)	N3—C30—H30C	109.5
C14—C15—H15	119.5	H30A—C30—H30C	109.5
C10—C15—H15	119.5	H30B—C30—H30C	109.5
C20—N1—C16	117.4 (2)	O8—C28—N3	123.5 (5)
C25—N2—C26	116.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4	0.95	2.25	2.905 (3)	125
C20—H20···O2^i	0.95	2.47	3.325 (3)	150
C16—H16···O8^ii	0.95	2.32	3.202 (4)	155

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

(QDP_IV)

Crystal data

C39H30N4O7	Z = 4
Mr = 666.67	F(000) = 1392
Monoclinic, P21/c	Dx = 1.399 Mg m^−3
a = 18.0656 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6584 (6) Å	µ = 0.10 mm^−1
c = 16.661 (1) Å	T = 150 K
β = 115.565 (2)°	Plate, yellow
V = 3165.5 (3) Å^3	0.30 × 0.20 × 0.15 mm

Data collection

Absorption correction: analytical Bruker, AXS, 2008	Rint = 0.038
Tmin = 0.977, Tmax = 0.985	θmax = 27.5°, θmin = 2.2°
27138 measured reflections	h = −22→23
7197 independent reflections	k = −14→15
5739 reflections with I > 2σ(I)	l = −21→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0488P)^2 + 1.7932P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
7197 reflections	Δρmax = 0.68 e Å^−3
497 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)
C8	0.24907 (9)	0.83777 (13)	0.24989 (10)	0.0171 (3)
C7	0.20403 (9)	0.75191 (13)	0.18346 (10)	0.0185 (3)
C6	0.13938 (9)	0.69305 (12)	0.19485 (9)	0.0168 (3)
C5	0.08766 (9)	0.61084 (13)	0.13235 (10)	0.0194 (3)
C4	0.02654 (9)	0.55611 (14)	0.14597 (10)	0.0212 (3)
H4	−0.0078	0.5017	0.1039	0.025*
C3	0.01522 (9)	0.58113 (14)	0.22248 (10)	0.0207 (3)
C2	0.06473 (9)	0.66085 (13)	0.28514 (10)	0.0196 (3)
H2	0.0571	0.6772	0.3369	0.023*
C1	0.12524 (9)	0.71537 (12)	0.26953 (9)	0.0160 (3)
C9	0.23078 (8)	0.85735 (12)	0.32036 (9)	0.0148 (3)
C10	0.26511 (9)	0.94336 (12)	0.39125 (9)	0.0152 (3)
C11	0.33837 (9)	1.00262 (12)	0.40892 (10)	0.0171 (3)
H11	0.3690	0.9838	0.3765	0.021*
C12	0.36656 (9)	1.08819 (13)	0.47304 (10)	0.0179 (3)
C13	0.32267 (9)	1.11430 (13)	0.52301 (10)	0.0182 (3)
C14	0.25069 (9)	1.05487 (13)	0.50593 (10)	0.0185 (3)
H14	0.2208	1.0724	0.5393	0.022*
C15	0.22179 (9)	0.97058 (13)	0.44111 (9)	0.0168 (3)
H15	0.1724	0.9310	0.4304	0.020*
O1	−0.04539 (7)	0.52590 (11)	0.23338 (8)	0.0294 (3)
O2	0.09958 (7)	0.58703 (11)	0.05914 (7)	0.0267 (3)
O3	0.21968 (7)	0.73393 (10)	0.11786 (7)	0.0277 (3)
O4	0.30761 (7)	0.90017 (10)	0.23958 (8)	0.0234 (3)
O5	0.43663 (7)	1.14884 (10)	0.49117 (7)	0.0248 (3)
O6	0.35355 (7)	1.19665 (9)	0.58681 (7)	0.0234 (3)
O7	0.17189 (6)	0.79333 (9)	0.33133 (7)	0.0170 (2)
C28	0.51394 (10)	0.02744 (14)	0.33534 (10)	0.0226 (3)
H28	0.5121	−0.0432	0.3629	0.027*
C29	0.54421 (10)	0.02701 (14)	0.27174 (11)	0.0233 (3)
H29	0.5628	−0.0425	0.2569	0.028*
C30	0.54715 (9)	0.12933 (13)	0.22959 (10)	0.0188 (3)
C31	0.52020 (11)	0.22703 (15)	0.25600 (12)	0.0293 (4)
H31	0.5219	0.2991	0.2303	0.035*
C32	0.49075 (11)	0.21957 (15)	0.31994 (12)	0.0303 (4)
H32	0.4720	0.2878	0.3363	0.036*
C33	0.57657 (9)	0.13835 (14)	0.16021 (11)	0.0216 (3)
C34	0.58913 (9)	0.05178 (14)	0.11567 (10)	0.0209 (3)
C35	0.61757 (9)	0.06396 (14)	0.04543 (10)	0.0201 (3)
C36	0.64047 (10)	0.17002 (15)	0.02398 (11)	0.0261 (4)
H36	0.6377	0.2372	0.0548	0.031*
C37	0.66709 (11)	0.17695 (15)	−0.04211 (11)	0.0274 (4)
H37	0.6834	0.2496	−0.0547	0.033*
C38	0.64847 (9)	−0.01577 (14)	−0.06959 (10)	0.0218 (3)
H38	0.6503	−0.0810	−0.1029	0.026*
C40	0.62264 (9)	−0.03125 (14)	−0.00308 (10)	0.0212 (3)
H40	0.6086	−0.1055	0.0094	0.025*
N3	0.48725 (8)	0.12187 (12)	0.35991 (9)	0.0216 (3)
N4	0.67101 (8)	0.08547 (12)	−0.08968 (9)	0.0231 (3)
C16	0.25596 (10)	0.40652 (14)	0.22258 (11)	0.0250 (4)
H16	0.2680	0.4752	0.1998	0.030*
C17	0.21853 (11)	0.41535 (15)	0.27930 (11)	0.0276 (4)
H17	0.2062	0.4886	0.2953	0.033*
C18	0.19901 (10)	0.31580 (16)	0.31290 (10)	0.0267 (4)
C19	0.21883 (10)	0.21217 (15)	0.28634 (11)	0.0282 (4)
H19	0.2059	0.1421	0.3064	0.034*
C20	0.25748 (10)	0.21097 (15)	0.23061 (11)	0.0270 (4)
H20	0.2715	0.1388	0.2146	0.032*
C21	0.15987 (12)	0.3112 (2)	0.37430 (13)	0.0220 (8)	0.864 (10)
C21A	0.1764 (8)	0.3765 (16)	0.3834 (8)	0.020 (4)*	0.136 (10)
C22	0.15435 (11)	0.40133 (18)	0.42012 (13)	0.0241 (6)	0.863 (6)
C22A	0.1430 (6)	0.3033 (9)	0.4241 (7)	0.016 (4)*	0.137 (6)
C23	0.12065 (10)	0.40073 (18)	0.48708 (12)	0.0342 (4)
C24	0.08726 (12)	0.30336 (19)	0.50876 (13)	0.0403 (5)
H24	0.0838	0.2327	0.4789	0.048*
C25	0.05896 (11)	0.31141 (18)	0.57522 (13)	0.0362 (4)
H25	0.0374	0.2448	0.5904	0.043*
C26	0.09219 (10)	0.50152 (18)	0.59378 (11)	0.0318 (4)
H26	0.0929	0.5724	0.6222	0.038*
C27	0.12282 (11)	0.50064 (19)	0.53108 (12)	0.0355 (4)
H27	0.1451	0.5684	0.5186	0.043*
N1	0.27623 (8)	0.30606 (12)	0.19792 (9)	0.0240 (3)
N2	0.06143 (8)	0.40985 (13)	0.61773 (9)	0.0290 (3)
H33	0.5842 (11)	0.2176 (17)	0.1471 (12)	0.028 (5)*
H21	0.1770 (12)	0.4730 (18)	0.4117 (13)	0.034 (5)*
H34	0.5795 (11)	−0.0267 (17)	0.1282 (12)	0.033 (5)*
H22	0.1373 (12)	0.2356 (18)	0.3841 (13)	0.033 (5)*
H5O	0.4549 (13)	1.1322 (18)	0.4452 (14)	0.041 (6)*
H6O	0.3228 (13)	1.1962 (19)	0.6217 (15)	0.048 (6)*
H2O	0.1411 (14)	0.6301 (19)	0.0626 (14)	0.043 (6)*
H4O	0.3070 (15)	0.893 (2)	0.1850 (18)	0.063 (8)*
H1O	−0.0500 (14)	0.556 (2)	0.2841 (17)	0.058 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C8	0.0187 (7)	0.0172 (7)	0.0177 (7)	−0.0020 (6)	0.0100 (6)	0.0004 (6)
C7	0.0218 (7)	0.0195 (7)	0.0162 (7)	0.0000 (6)	0.0102 (6)	−0.0010 (6)
C6	0.0180 (7)	0.0176 (7)	0.0150 (7)	0.0001 (6)	0.0074 (6)	0.0001 (6)
C5	0.0208 (7)	0.0228 (8)	0.0154 (7)	−0.0001 (6)	0.0086 (6)	−0.0022 (6)
C4	0.0192 (7)	0.0241 (8)	0.0197 (7)	−0.0048 (6)	0.0078 (6)	−0.0059 (6)
C3	0.0164 (7)	0.0250 (8)	0.0215 (8)	−0.0034 (6)	0.0090 (6)	−0.0017 (6)
C2	0.0194 (7)	0.0245 (8)	0.0177 (7)	−0.0018 (6)	0.0108 (6)	−0.0031 (6)
C1	0.0157 (7)	0.0164 (7)	0.0142 (7)	0.0007 (6)	0.0050 (6)	−0.0011 (5)
C9	0.0151 (7)	0.0146 (7)	0.0155 (7)	0.0000 (5)	0.0075 (6)	0.0011 (5)
C10	0.0182 (7)	0.0157 (7)	0.0125 (6)	0.0021 (6)	0.0072 (6)	0.0013 (5)
C11	0.0204 (7)	0.0181 (7)	0.0160 (7)	0.0007 (6)	0.0108 (6)	0.0002 (6)
C12	0.0204 (7)	0.0191 (7)	0.0166 (7)	−0.0034 (6)	0.0103 (6)	−0.0004 (6)
C13	0.0246 (8)	0.0163 (7)	0.0152 (7)	−0.0011 (6)	0.0099 (6)	−0.0015 (6)
C14	0.0220 (7)	0.0220 (8)	0.0167 (7)	0.0008 (6)	0.0131 (6)	−0.0009 (6)
C15	0.0168 (7)	0.0191 (7)	0.0159 (7)	−0.0016 (6)	0.0083 (6)	0.0008 (6)
O1	0.0256 (6)	0.0414 (7)	0.0276 (6)	−0.0163 (5)	0.0174 (5)	−0.0134 (6)
O2	0.0296 (6)	0.0348 (7)	0.0216 (6)	−0.0119 (5)	0.0166 (5)	−0.0118 (5)
O3	0.0353 (7)	0.0335 (7)	0.0240 (6)	−0.0127 (5)	0.0218 (5)	−0.0110 (5)
O4	0.0294 (6)	0.0282 (6)	0.0199 (6)	−0.0118 (5)	0.0176 (5)	−0.0078 (5)
O5	0.0285 (6)	0.0304 (6)	0.0225 (6)	−0.0131 (5)	0.0176 (5)	−0.0091 (5)
O6	0.0320 (6)	0.0231 (6)	0.0218 (6)	−0.0092 (5)	0.0178 (5)	−0.0093 (5)
O7	0.0190 (5)	0.0198 (5)	0.0152 (5)	−0.0043 (4)	0.0101 (4)	−0.0033 (4)
C28	0.0284 (8)	0.0219 (8)	0.0216 (8)	−0.0040 (6)	0.0145 (7)	−0.0003 (6)
C29	0.0304 (9)	0.0205 (8)	0.0253 (8)	−0.0021 (7)	0.0180 (7)	−0.0018 (6)
C30	0.0171 (7)	0.0239 (8)	0.0168 (7)	−0.0010 (6)	0.0086 (6)	0.0006 (6)
C31	0.0409 (10)	0.0239 (9)	0.0348 (9)	0.0083 (7)	0.0274 (8)	0.0099 (7)
C32	0.0406 (10)	0.0253 (9)	0.0385 (10)	0.0087 (7)	0.0296 (9)	0.0053 (7)
C33	0.0225 (8)	0.0243 (8)	0.0214 (8)	−0.0014 (6)	0.0128 (6)	0.0026 (6)
C34	0.0222 (8)	0.0247 (8)	0.0184 (7)	−0.0046 (6)	0.0113 (6)	0.0005 (6)
C35	0.0184 (7)	0.0265 (8)	0.0162 (7)	−0.0045 (6)	0.0083 (6)	−0.0021 (6)
C36	0.0347 (9)	0.0260 (9)	0.0246 (8)	−0.0114 (7)	0.0194 (7)	−0.0092 (7)
C37	0.0359 (9)	0.0272 (9)	0.0276 (9)	−0.0124 (7)	0.0215 (8)	−0.0067 (7)
C38	0.0227 (8)	0.0254 (8)	0.0192 (7)	−0.0025 (6)	0.0109 (6)	−0.0039 (6)
C40	0.0216 (8)	0.0225 (8)	0.0211 (7)	−0.0036 (6)	0.0107 (6)	−0.0005 (6)
N3	0.0211 (6)	0.0267 (7)	0.0208 (7)	−0.0013 (5)	0.0127 (6)	−0.0002 (6)
N4	0.0261 (7)	0.0282 (7)	0.0202 (7)	−0.0070 (6)	0.0149 (6)	−0.0045 (6)
C16	0.0308 (9)	0.0241 (8)	0.0204 (8)	0.0004 (7)	0.0113 (7)	0.0046 (6)
C17	0.0332 (9)	0.0292 (9)	0.0210 (8)	0.0096 (7)	0.0122 (7)	0.0010 (7)
C18	0.0209 (8)	0.0421 (10)	0.0174 (7)	0.0077 (7)	0.0086 (6)	0.0073 (7)
C19	0.0284 (9)	0.0312 (9)	0.0268 (9)	0.0028 (7)	0.0135 (7)	0.0118 (7)
C20	0.0319 (9)	0.0241 (8)	0.0268 (8)	0.0065 (7)	0.0145 (7)	0.0054 (7)
C21	0.0212 (10)	0.0259 (17)	0.0209 (10)	0.0013 (9)	0.0110 (8)	0.0035 (8)
C22	0.0219 (10)	0.0296 (13)	0.0222 (10)	−0.0017 (8)	0.0108 (8)	0.0015 (8)
C23	0.0182 (8)	0.0568 (12)	0.0277 (9)	−0.0009 (8)	0.0099 (7)	0.0021 (9)
C24	0.0306 (10)	0.0538 (12)	0.0310 (10)	0.0022 (9)	0.0081 (8)	−0.0195 (9)
C25	0.0272 (9)	0.0467 (12)	0.0379 (10)	−0.0102 (8)	0.0170 (8)	−0.0162 (9)
C26	0.0216 (8)	0.0488 (11)	0.0255 (9)	−0.0110 (8)	0.0104 (7)	−0.0061 (8)
C27	0.0230 (8)	0.0570 (12)	0.0270 (9)	−0.0069 (8)	0.0112 (7)	−0.0013 (9)
N1	0.0271 (7)	0.0280 (7)	0.0203 (7)	0.0044 (6)	0.0136 (6)	0.0054 (6)
N2	0.0232 (7)	0.0428 (9)	0.0260 (7)	−0.0105 (6)	0.0154 (6)	−0.0111 (7)

Geometric parameters (Å, º)

C8—O4	1.3543 (18)	C34—C35	1.474 (2)
C8—C9	1.369 (2)	C34—H34	0.97 (2)
C8—C7	1.453 (2)	C35—C36	1.398 (2)
C7—O3	1.2590 (18)	C35—C40	1.399 (2)
C7—C6	1.436 (2)	C36—C37	1.381 (2)
C6—C1	1.398 (2)	C36—H36	0.9500
C6—C5	1.427 (2)	C37—N4	1.349 (2)
C5—O2	1.3558 (18)	C37—H37	0.9500
C5—C4	1.376 (2)	C38—N4	1.337 (2)
C4—C3	1.406 (2)	C38—C40	1.387 (2)
C4—H4	0.9500	C38—H38	0.9500
C3—O1	1.3485 (18)	C40—H40	0.9500
C3—C2	1.396 (2)	C16—N1	1.343 (2)
C2—C1	1.383 (2)	C16—C17	1.383 (2)
C2—H2	0.9500	C16—H16	0.9500
C1—O7	1.3593 (17)	C17—C18	1.398 (2)
C9—O7	1.3749 (17)	C17—H17	0.9500
C9—C10	1.467 (2)	C18—C19	1.386 (3)
C10—C15	1.402 (2)	C18—C21	1.474 (2)
C10—C11	1.407 (2)	C18—C21A	1.569 (14)
C11—C12	1.388 (2)	C19—C20	1.382 (2)
C11—H11	0.9500	C19—H19	0.9500
C12—O5	1.3652 (18)	C20—N1	1.341 (2)
C12—C13	1.409 (2)	C20—H20	0.9500
C13—O6	1.3605 (18)	C21—C21A	0.808 (17)
C13—C14	1.390 (2)	C21—C22A	1.003 (12)
C14—C15	1.385 (2)	C21—C22	1.328 (3)
C14—H14	0.9500	C21—H22	1.01 (2)
C15—H15	0.9500	C21A—C22	0.909 (14)
O1—H1O	0.95 (3)	C21A—C22A	1.38 (2)
O2—H2O	0.88 (2)	C21A—H21	1.22 (3)
O4—H4O	0.91 (3)	C22—C22A	1.168 (11)
O5—H5O	0.98 (2)	C22—C23	1.484 (3)
O6—H6O	0.96 (2)	C22—H21	0.97 (2)
C28—N3	1.335 (2)	C22A—C23	1.709 (11)
C28—C29	1.386 (2)	C22A—H22	1.01 (2)
C28—H28	0.9500	C23—C27	1.368 (3)
C29—C30	1.397 (2)	C23—C24	1.404 (3)
C29—H29	0.9500	C24—C25	1.409 (3)
C30—C31	1.383 (2)	C24—H24	0.9500
C30—C33	1.470 (2)	C25—N2	1.339 (2)
C31—C32	1.384 (2)	C25—H25	0.9500
C31—H31	0.9500	C26—N2	1.342 (2)
C32—N3	1.335 (2)	C26—C27	1.377 (2)
C32—H32	0.9500	C26—H26	0.9500
C33—C34	1.329 (2)	C27—H27	0.9500
C33—H33	0.972 (19)
O4—C8—C9	120.66 (13)	C38—C40—C35	119.12 (15)
O4—C8—C7	118.99 (13)	C38—C40—H40	120.4
C9—C8—C7	120.33 (13)	C35—C40—H40	120.4
O3—C7—C6	122.36 (14)	C32—N3—C28	116.72 (13)
O3—C7—C8	120.94 (14)	C38—N4—C37	116.87 (14)
C6—C7—C8	116.65 (13)	N1—C16—C17	123.52 (15)
C1—C6—C5	117.43 (13)	N1—C16—H16	118.2
C1—C6—C7	119.99 (13)	C17—C16—H16	118.2
C5—C6—C7	122.57 (13)	C16—C17—C18	119.60 (16)
O2—C5—C4	120.24 (14)	C16—C17—H17	120.2
O2—C5—C6	119.07 (13)	C18—C17—H17	120.2
C4—C5—C6	120.69 (14)	C19—C18—C17	116.83 (15)
C5—C4—C3	119.62 (14)	C19—C18—C21	117.20 (17)
C5—C4—H4	120.2	C17—C18—C21	125.97 (18)
C3—C4—H4	120.2	C19—C18—C21A	145.0 (6)
O1—C3—C2	120.85 (14)	C17—C18—C21A	96.7 (7)
O1—C3—C4	117.86 (14)	C21—C18—C21A	30.6 (6)
C2—C3—C4	121.29 (14)	C20—C19—C18	119.90 (16)
C1—C2—C3	117.96 (14)	C20—C19—H19	120.0
C1—C2—H2	121.0	C18—C19—H19	120.0
C3—C2—H2	121.0	N1—C20—C19	123.62 (16)
O7—C1—C2	116.55 (13)	N1—C20—H20	118.2
O7—C1—C6	120.45 (13)	C19—C20—H20	118.2
C2—C1—C6	123.00 (13)	C21A—C21—C22A	98.7 (12)
C8—C9—O7	120.70 (13)	C21A—C21—C22	42.2 (10)
C8—C9—C10	129.02 (13)	C22A—C21—C22	58.2 (6)
O7—C9—C10	110.27 (12)	C21A—C21—C18	81.2 (10)
C15—C10—C11	118.71 (13)	C22A—C21—C18	169.8 (6)
C15—C10—C9	118.79 (13)	C22—C21—C18	123.2 (2)
C11—C10—C9	122.46 (13)	C21A—C21—H22	158.7 (15)
C12—C11—C10	120.90 (14)	C22A—C21—H22	60.1 (12)
C12—C11—H11	119.6	C22—C21—H22	117.5 (12)
C10—C11—H11	119.6	C18—C21—H22	119.3 (12)
O5—C12—C11	122.66 (13)	C21—C21A—C22	101.1 (18)
O5—C12—C13	117.52 (13)	C21—C21A—C22A	46.0 (10)
C11—C12—C13	119.82 (13)	C22—C21A—C22A	57.0 (11)
O6—C13—C14	122.94 (13)	C21—C21A—C18	68.2 (10)
O6—C13—C12	117.94 (13)	C22—C21A—C18	168.1 (18)
C14—C13—C12	119.12 (13)	C22A—C21A—C18	113.5 (13)
C15—C14—C13	121.19 (14)	C21—C21A—H21	152 (2)
C15—C14—H14	119.4	C22—C21A—H21	51.6 (13)
C13—C14—H14	119.4	C22A—C21A—H21	108.3 (15)
C14—C15—C10	120.25 (13)	C18—C21A—H21	138.1 (17)
C14—C15—H15	119.9	C21A—C22—C22A	82.2 (14)
C10—C15—H15	119.9	C21A—C22—C21	36.7 (12)
C3—O1—H1O	109.5 (14)	C22A—C22—C21	46.9 (6)
C5—O2—H2O	106.6 (14)	C21A—C22—C23	161.0 (12)
C8—O4—H4O	113.8 (16)	C22A—C22—C23	79.3 (6)
C12—O5—H5O	108.6 (12)	C21—C22—C23	125.84 (19)
C13—O6—H6O	108.6 (13)	C21A—C22—H21	80.9 (16)
C1—O7—C9	121.64 (11)	C22A—C22—H21	161.7 (13)
N3—C28—C29	123.44 (15)	C21—C22—H21	117.4 (12)
N3—C28—H28	118.3	C23—C22—H21	116.7 (12)
C29—C28—H28	118.3	C21—C22A—C22	75.0 (8)
C28—C29—C30	119.63 (15)	C21—C22A—C21A	35.4 (7)
C28—C29—H29	120.2	C22—C22A—C21A	40.8 (7)
C30—C29—H29	120.2	C21—C22A—C23	133.1 (9)
C31—C30—C29	116.63 (14)	C22—C22A—C23	58.5 (5)
C31—C30—C33	119.19 (14)	C21A—C22A—C23	99.2 (9)
C29—C30—C33	124.18 (14)	C21—C22A—H22	60.4 (14)
C30—C31—C32	119.88 (15)	C22—C22A—H22	134.3 (17)
C30—C31—H31	120.1	C21A—C22A—H22	95.8 (17)
C32—C31—H31	120.1	C23—C22A—H22	160.3 (15)
N3—C32—C31	123.68 (15)	C27—C23—C24	117.82 (17)
N3—C32—H32	118.2	C27—C23—C22	118.21 (18)
C31—C32—H32	118.2	C24—C23—C22	123.96 (18)
C34—C33—C30	126.27 (15)	C27—C23—C22A	159.3 (4)
C34—C33—H33	121.4 (11)	C24—C23—C22A	82.1 (4)
C30—C33—H33	112.2 (11)	C22—C23—C22A	42.2 (4)
C33—C34—C35	124.90 (15)	C23—C24—C25	119.36 (18)
C33—C34—H34	120.5 (11)	C23—C24—H24	120.3
C35—C34—H34	114.6 (11)	C25—C24—H24	120.3
C36—C35—C40	116.98 (14)	N2—C25—C24	122.16 (19)
C36—C35—C34	122.07 (14)	N2—C25—H25	118.9
C40—C35—C34	120.95 (14)	C24—C25—H25	118.9
C37—C36—C35	119.91 (15)	N2—C26—C27	124.96 (18)
C37—C36—H36	120.0	N2—C26—H26	117.5
C35—C36—H36	120.0	C27—C26—H26	117.5
N4—C37—C36	123.16 (15)	C23—C27—C26	119.01 (19)
N4—C37—H37	118.4	C23—C27—H27	120.5
C36—C37—H37	118.4	C26—C27—H27	120.5
N4—C38—C40	123.95 (15)	C20—N1—C16	116.51 (14)
N4—C38—H38	118.0	C25—N2—C26	116.65 (15)
C40—C38—H38	118.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4	0.95	2.28	2.8884 (18)	121
C28—H28···O5^i	0.95	2.52	3.339 (2)	145
C37—H37···O3^ii	0.95	2.41	3.014 (2)	121
C38—H38···O6^iii	0.95	2.61	3.364 (2)	137
O6—H6O···N1^iv	0.96 (2)	1.80 (2)	2.7588 (17)	173 (2)
O5—H5O···N3^v	0.98 (2)	1.76 (2)	2.7283 (17)	172.4 (19)
O2—H2O···O3	0.88 (2)	1.79 (2)	2.6012 (16)	152 (2)
O4—H4O···N4^ii	0.91 (3)	1.81 (3)	2.6920 (17)	162 (2)
O1—H1O···N2^vi	0.95 (3)	1.78 (3)	2.7237 (18)	172 (2)

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

(QDP_V)

Crystal data

C27H20N2O7	Z = 8
Mr = 484.45	F(000) = 2016
Monoclinic, C2/c	Dx = 1.471 Mg m^−3
a = 21.831 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.904 (3) Å	µ = 0.11 mm^−1
c = 15.876 (4) Å	T = 150 K
β = 101.912 (7)°	Plate, yellow-red
V = 4376.0 (17) Å^3	0.30 × 0.20 × 0.12 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.071
Tmin = 0.777, Tmax = 1.000	θmax = 27.5°, θmin = 3.0°
18633 measured reflections	h = −28→28
5006 independent reflections	k = −16→16
3202 reflections with I > 2σ(I)	l = −20→20

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)] = 0.055	w = 1/[σ^2(Fo^2) + (0.0666P)^2 + 1.7713P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.150	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.27 e Å^−3
5006 reflections	Δρmin = −0.32 e Å^−3
354 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0006 (2)

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
H21	0.0379 (13)	0.065 (2)	0.0950 (17)	0.048 (8)*
H22	0.0531 (13)	−0.152 (2)	0.1304 (17)	0.047 (8)*
H1O	0.1654 (14)	0.532 (2)	0.3618 (18)	0.049 (9)*
H4O	0.0952 (14)	0.736 (2)	−0.1476 (19)	0.053 (9)*
H5O	−0.1940 (18)	0.767 (3)	−0.292 (2)	0.088 (12)*
H6O	−0.2719 (16)	0.638 (3)	−0.180 (2)	0.079 (11)*
H2O	0.2257 (17)	0.685 (3)	0.063 (3)	0.093 (13)*
O7	0.01694 (7)	0.61846 (13)	0.05473 (10)	0.0271 (4)
O4	0.05930 (8)	0.72676 (14)	−0.13554 (11)	0.0347 (5)
O3	0.17244 (7)	0.71207 (13)	−0.02782 (10)	0.0311 (4)
O2	0.23936 (7)	0.66665 (14)	0.12425 (11)	0.0308 (4)
O6	−0.23927 (7)	0.67339 (14)	−0.20629 (11)	0.0333 (4)
O1	0.12848 (8)	0.53177 (15)	0.32979 (11)	0.0355 (5)
O5	−0.14912 (7)	0.75920 (14)	−0.27412 (10)	0.0320 (4)
C9	0.01134 (10)	0.65708 (18)	−0.02736 (14)	0.0242 (5)
C6	0.12798 (10)	0.64523 (17)	0.08488 (15)	0.0228 (5)
C8	0.06357 (10)	0.68792 (18)	−0.05524 (15)	0.0252 (5)
C10	−0.05391 (10)	0.66014 (18)	−0.07338 (14)	0.0232 (5)
C7	0.12527 (10)	0.68296 (17)	−0.00028 (15)	0.0235 (5)
C4	0.18637 (10)	0.59873 (18)	0.22772 (14)	0.0266 (5)
H4	0.2249	0.5942	0.2684	0.032*
C11	−0.07148 (10)	0.70604 (18)	−0.15461 (14)	0.0246 (5)
H11	−0.0404	0.7349	−0.1815	0.030*
C14	−0.16330 (10)	0.61962 (18)	−0.07870 (15)	0.0259 (5)
H14	−0.1945	0.5895	−0.0527	0.031*
C2	0.07365 (10)	0.57338 (19)	0.19143 (15)	0.0274 (5)
H2	0.0359	0.5512	0.2066	0.033*
C5	0.18477 (10)	0.63611 (18)	0.14628 (15)	0.0239 (5)
C15	−0.10103 (10)	0.61731 (18)	−0.03565 (15)	0.0259 (5)
H15	−0.0902	0.5865	0.0198	0.031*
C12	−0.13341 (10)	0.70972 (18)	−0.19586 (14)	0.0237 (5)
C3	0.13020 (11)	0.56726 (18)	0.24998 (15)	0.0271 (5)
C13	−0.18029 (10)	0.66534 (18)	−0.15904 (15)	0.0245 (5)
C1	0.07356 (10)	0.61243 (18)	0.11075 (14)	0.0238 (5)
N1	0.25012 (9)	0.02241 (16)	0.07618 (12)	0.0288 (5)
N2	−0.15875 (9)	−0.10312 (17)	0.15754 (13)	0.0336 (5)
C18	0.12506 (10)	0.00561 (19)	0.09371 (15)	0.0269 (5)
C20	0.22740 (11)	−0.0655 (2)	0.10279 (16)	0.0319 (6)
H20	0.2547	−0.1233	0.1151	0.038*
C21	0.05978 (11)	0.0015 (2)	0.10428 (17)	0.0326 (6)
C23	−0.03430 (11)	−0.08597 (19)	0.13739 (15)	0.0295 (6)
C19	0.16669 (11)	−0.0767 (2)	0.11331 (16)	0.0333 (6)
H19	0.1533	−0.1403	0.1338	0.040*
C16	0.20971 (11)	0.10127 (19)	0.05684 (15)	0.0293 (6)
H16	0.2245	0.1641	0.0370	0.035*
C17	0.14814 (11)	0.09635 (19)	0.06413 (15)	0.0289 (5)
H17	0.1214	0.1545	0.0491	0.035*
C22	0.03074 (11)	−0.0817 (2)	0.12597 (17)	0.0328 (6)
C27	−0.06167 (11)	−0.1816 (2)	0.14546 (17)	0.0360 (6)
H27	−0.0382	−0.2434	0.1445	0.043*
C24	−0.07145 (11)	0.0013 (2)	0.14033 (17)	0.0355 (6)
H24	−0.0550	0.0686	0.1353	0.043*
C26	−0.12290 (11)	−0.1865 (2)	0.15489 (18)	0.0373 (6)
H26	−0.1407	−0.2529	0.1598	0.045*
C25	−0.13250 (11)	−0.0109 (2)	0.15062 (17)	0.0365 (6)
H25	−0.1570	0.0495	0.1529	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0163 (8)	0.0407 (10)	0.0242 (9)	0.0003 (7)	0.0038 (6)	0.0064 (8)
O4	0.0166 (9)	0.0601 (12)	0.0276 (9)	−0.0004 (8)	0.0052 (7)	0.0109 (9)
O3	0.0188 (8)	0.0451 (11)	0.0301 (9)	−0.0027 (7)	0.0068 (7)	0.0041 (8)
O2	0.0172 (8)	0.0466 (11)	0.0286 (10)	−0.0040 (7)	0.0044 (7)	0.0031 (8)
O6	0.0137 (8)	0.0511 (12)	0.0339 (10)	−0.0022 (7)	0.0023 (7)	0.0059 (9)
O1	0.0240 (9)	0.0559 (13)	0.0259 (10)	−0.0015 (8)	0.0036 (7)	0.0094 (9)
O5	0.0182 (9)	0.0517 (11)	0.0262 (9)	0.0037 (7)	0.0052 (7)	0.0079 (8)
C9	0.0218 (11)	0.0288 (13)	0.0225 (12)	0.0009 (9)	0.0055 (9)	0.0020 (10)
C6	0.0184 (11)	0.0245 (13)	0.0257 (12)	0.0011 (9)	0.0050 (9)	−0.0011 (10)
C8	0.0203 (11)	0.0310 (13)	0.0244 (12)	0.0019 (9)	0.0053 (9)	0.0015 (10)
C10	0.0167 (11)	0.0284 (13)	0.0245 (12)	0.0012 (9)	0.0044 (9)	−0.0021 (10)
C7	0.0195 (11)	0.0269 (13)	0.0249 (12)	0.0023 (9)	0.0066 (9)	−0.0029 (10)
C4	0.0173 (11)	0.0357 (14)	0.0256 (12)	0.0005 (9)	0.0017 (9)	0.0005 (11)
C11	0.0185 (11)	0.0309 (13)	0.0258 (12)	−0.0002 (9)	0.0080 (9)	0.0012 (10)
C14	0.0194 (11)	0.0319 (13)	0.0282 (13)	−0.0017 (9)	0.0086 (9)	0.0005 (11)
C2	0.0189 (11)	0.0365 (14)	0.0276 (13)	0.0000 (10)	0.0068 (9)	0.0009 (11)
C5	0.0187 (11)	0.0265 (13)	0.0266 (13)	−0.0023 (9)	0.0049 (9)	−0.0030 (10)
C15	0.0241 (12)	0.0293 (13)	0.0251 (12)	−0.0014 (10)	0.0068 (9)	0.0006 (11)
C12	0.0190 (11)	0.0304 (13)	0.0217 (12)	0.0025 (9)	0.0041 (9)	0.0012 (10)
C3	0.0264 (12)	0.0298 (13)	0.0258 (13)	0.0017 (10)	0.0073 (9)	0.0009 (11)
C13	0.0147 (10)	0.0311 (13)	0.0277 (13)	0.0003 (9)	0.0046 (9)	−0.0033 (10)
C1	0.0161 (11)	0.0278 (13)	0.0266 (12)	0.0017 (9)	0.0021 (9)	−0.0010 (10)
N1	0.0251 (10)	0.0355 (12)	0.0267 (11)	0.0000 (9)	0.0073 (8)	−0.0009 (9)
N2	0.0212 (11)	0.0443 (14)	0.0360 (12)	−0.0017 (9)	0.0075 (9)	0.0034 (10)
C18	0.0222 (12)	0.0329 (14)	0.0258 (12)	−0.0013 (10)	0.0053 (9)	−0.0026 (11)
C20	0.0264 (13)	0.0340 (14)	0.0356 (14)	0.0031 (10)	0.0068 (10)	0.0014 (12)
C21	0.0246 (13)	0.0362 (15)	0.0373 (15)	0.0024 (11)	0.0069 (11)	0.0016 (12)
C23	0.0227 (12)	0.0372 (15)	0.0290 (13)	−0.0019 (10)	0.0063 (10)	−0.0001 (11)
C19	0.0307 (13)	0.0327 (14)	0.0383 (15)	−0.0006 (11)	0.0115 (11)	0.0019 (12)
C16	0.0274 (13)	0.0325 (14)	0.0287 (13)	−0.0047 (10)	0.0074 (10)	0.0007 (11)
C17	0.0264 (12)	0.0331 (14)	0.0268 (13)	0.0024 (10)	0.0047 (10)	0.0008 (11)
C22	0.0263 (13)	0.0363 (15)	0.0375 (15)	0.0005 (11)	0.0101 (11)	−0.0004 (12)
C27	0.0289 (13)	0.0362 (15)	0.0450 (16)	0.0038 (11)	0.0121 (11)	0.0048 (13)
C24	0.0303 (14)	0.0316 (14)	0.0462 (16)	−0.0033 (11)	0.0115 (11)	−0.0040 (12)
C26	0.0293 (14)	0.0339 (15)	0.0497 (17)	−0.0034 (11)	0.0106 (12)	0.0080 (13)
C25	0.0253 (13)	0.0397 (16)	0.0456 (16)	0.0013 (11)	0.0100 (11)	−0.0028 (13)

Geometric parameters (Å, º)

O7—C1	1.368 (2)	C2—C3	1.386 (3)
O7—C9	1.377 (3)	C2—H2	0.9500
O4—C8	1.355 (3)	C15—H15	0.9500
O4—H4O	0.85 (3)	C12—C13	1.401 (3)
O3—C7	1.256 (3)	N1—C16	1.340 (3)
O2—C5	1.368 (3)	N1—C20	1.340 (3)
O2—H2O	0.98 (4)	N2—C25	1.335 (3)
O6—C13	1.354 (3)	N2—C26	1.336 (3)
O6—H6O	1.01 (4)	C18—C19	1.391 (3)
O1—C3	1.355 (3)	C18—C17	1.394 (3)
O1—H1O	0.86 (3)	C18—C21	1.470 (3)
O5—C12	1.376 (3)	C20—C19	1.378 (3)
O5—H5O	0.97 (4)	C20—H20	0.9500
C9—C8	1.365 (3)	C21—C22	1.328 (4)
C9—C10	1.461 (3)	C21—H21	0.94 (3)
C6—C1	1.400 (3)	C23—C27	1.388 (3)
C6—C5	1.415 (3)	C23—C24	1.394 (3)
C6—C7	1.427 (3)	C23—C22	1.469 (3)
C8—C7	1.447 (3)	C19—H19	0.9500
C10—C11	1.399 (3)	C16—C17	1.374 (3)
C10—C15	1.406 (3)	C16—H16	0.9500
C4—C5	1.374 (3)	C17—H17	0.9500
C4—C3	1.404 (3)	C22—H22	1.02 (3)
C4—H4	0.9500	C27—C26	1.377 (3)
C11—C12	1.376 (3)	C27—H27	0.9500
C11—H11	0.9500	C24—C25	1.385 (3)
C14—C13	1.385 (3)	C24—H24	0.9500
C14—C15	1.390 (3)	C26—H26	0.9500
C14—H14	0.9500	C25—H25	0.9500
C2—C1	1.376 (3)
C1—O7—C9	121.85 (17)	O6—C13—C14	125.91 (19)
C8—O4—H4O	112 (2)	O6—C13—C12	115.5 (2)
C5—O2—H2O	103 (2)	C14—C13—C12	118.6 (2)
C13—O6—H6O	114.1 (19)	O7—C1—C2	116.97 (19)
C3—O1—H1O	110.3 (19)	O7—C1—C6	120.0 (2)
C12—O5—H5O	111 (2)	C2—C1—C6	123.1 (2)
C8—C9—O7	119.71 (19)	C16—N1—C20	116.5 (2)
C8—C9—C10	128.6 (2)	C25—N2—C26	116.8 (2)
O7—C9—C10	111.72 (18)	C19—C18—C17	116.9 (2)
C1—C6—C5	116.7 (2)	C19—C18—C21	123.4 (2)
C1—C6—C7	120.62 (19)	C17—C18—C21	119.7 (2)
C5—C6—C7	122.70 (19)	N1—C20—C19	123.7 (2)
O4—C8—C9	120.9 (2)	N1—C20—H20	118.1
O4—C8—C7	117.28 (19)	C19—C20—H20	118.1
C9—C8—C7	121.8 (2)	C22—C21—C18	125.8 (2)
C11—C10—C15	118.3 (2)	C22—C21—H21	119.2 (17)
C11—C10—C9	121.74 (19)	C18—C21—H21	115.0 (17)
C15—C10—C9	120.0 (2)	C27—C23—C24	116.8 (2)
O3—C7—C6	123.7 (2)	C27—C23—C22	119.3 (2)
O3—C7—C8	120.3 (2)	C24—C23—C22	123.9 (2)
C6—C7—C8	115.96 (19)	C20—C19—C18	119.5 (2)
C5—C4—C3	119.0 (2)	C20—C19—H19	120.2
C5—C4—H4	120.5	C18—C19—H19	120.2
C3—C4—H4	120.5	N1—C16—C17	123.7 (2)
C12—C11—C10	120.6 (2)	N1—C16—H16	118.2
C12—C11—H11	119.7	C17—C16—H16	118.2
C10—C11—H11	119.7	C16—C17—C18	119.7 (2)
C13—C14—C15	120.7 (2)	C16—C17—H17	120.2
C13—C14—H14	119.6	C18—C17—H17	120.2
C15—C14—H14	119.6	C21—C22—C23	126.0 (2)
C1—C2—C3	118.4 (2)	C21—C22—H22	119.0 (15)
C1—C2—H2	120.8	C23—C22—H22	114.7 (15)
C3—C2—H2	120.8	C26—C27—C23	119.8 (2)
O2—C5—C4	119.2 (2)	C26—C27—H27	120.1
O2—C5—C6	119.1 (2)	C23—C27—H27	120.1
C4—C5—C6	121.7 (2)	C25—C24—C23	119.6 (2)
C14—C15—C10	120.6 (2)	C25—C24—H24	120.2
C14—C15—H15	119.7	C23—C24—H24	120.2
C10—C15—H15	119.7	N2—C26—C27	123.7 (2)
O5—C12—C11	118.89 (19)	N2—C26—H26	118.2
O5—C12—C13	119.92 (19)	C27—C26—H26	118.2
C11—C12—C13	121.2 (2)	N2—C25—C24	123.4 (2)
O1—C3—C2	117.0 (2)	N2—C25—H25	118.3
O1—C3—C4	121.8 (2)	C24—C25—H25	118.3
C2—C3—C4	121.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1^i	0.86 (3)	1.91 (3)	2.763 (3)	174 (3)
O4—H4O···O3	0.85 (3)	2.29 (3)	2.705 (2)	110 (2)
O4—H4O···O5^ii	0.85 (3)	1.90 (3)	2.690 (2)	153 (3)
O5—H5O···O2^iii	0.97 (4)	1.95 (4)	2.797 (2)	144 (3)
O6—H6O···N2^iv	1.01 (4)	1.69 (4)	2.663 (2)	162 (3)
O2—H2O···O3	0.98 (4)	1.70 (4)	2.617 (2)	155 (3)
C4—H4···N1^i	0.95	2.59	3.287 (3)	131
C11—H11···O4	0.95	2.15	2.821 (3)	127
C20—H20···O3^v	0.95	2.58	3.294 (3)	132
C24—H24···O4^vi	0.95	2.64	3.521 (3)	154

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

(QDPE_I)

Crystal data

C31H30N2O8	V = 1336.8 (2) Å^3
Mr = 558.57	Z = 2
Triclinic, P1	F(000) = 588
a = 9.8782 (8) Å	Dx = 1.388 Mg m^−3
b = 11.5881 (10) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.041 (1) Å	µ = 0.10 mm^−1
α = 76.595 (5)°	T = 150 K
β = 85.792 (6)°	Plate, yellow
γ = 67.035 (5)°	0.40 × 0.20 × 0.20 mm

Data collection

Absorption correction: multi-scan Jacobson, R. (1998) Private communication	Rint = 0.036
Tmin = 0.777, Tmax = 1.000	θmax = 27.5°, θmin = 3.1°
14292 measured reflections	h = −12→12
6112 independent reflections	k = −15→15
4658 reflections with I > 2σ(I)	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.148	w = 1/[σ^2(Fo^2) + (0.0694P)^2 + 0.7053P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
6112 reflections	Δρmax = 0.44 e Å^−3
390 parameters	Δρmin = −0.41 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
O6	0.51143 (14)	0.16326 (14)	0.60018 (10)	0.0217 (3)
O2	0.86791 (14)	0.01705 (14)	1.30501 (10)	0.0228 (3)
O4	0.79544 (14)	0.05778 (13)	0.90931 (10)	0.0201 (3)
O5	0.46529 (12)	0.15248 (12)	1.06272 (9)	0.0155 (3)
O3	0.90792 (13)	0.01255 (13)	1.10428 (10)	0.0202 (3)
O1	0.38235 (14)	0.14333 (13)	1.42537 (9)	0.0203 (3)
O7	0.21239 (14)	0.26385 (13)	0.60970 (10)	0.0208 (3)
N2	−0.09696 (17)	0.77468 (17)	0.61763 (13)	0.0256 (4)
N1	0.92144 (17)	0.36095 (16)	0.64784 (13)	0.0232 (4)
C10	0.46706 (18)	0.16466 (16)	0.88119 (13)	0.0139 (3)
C6	0.67201 (18)	0.08304 (17)	1.17916 (13)	0.0149 (3)
C7	0.76941 (18)	0.05632 (17)	1.09337 (13)	0.0155 (3)
C14	0.22701 (19)	0.25178 (17)	0.79688 (14)	0.0171 (4)
H14	0.1230	0.2878	0.8018	0.021*
C11	0.53097 (18)	0.14629 (17)	0.78317 (13)	0.0151 (3)
H11	0.6350	0.1096	0.7782	0.018*
C8	0.70398 (18)	0.08199 (16)	0.99152 (13)	0.0146 (3)
C9	0.55445 (18)	0.13029 (16)	0.97741 (13)	0.0138 (3)
C28	0.2422 (4)	0.6370 (3)	0.9623 (3)	0.0722 (11)
H28A	0.3062	0.6620	1.0000	0.087*
H28B	0.2465	0.6704	0.8856	0.087*
C3	0.47243 (19)	0.12662 (17)	1.34262 (13)	0.0164 (4)
C15	0.31341 (18)	0.21784 (17)	0.88569 (13)	0.0159 (4)
H15	0.2680	0.2307	0.9511	0.019*
C5	0.72220 (18)	0.06103 (17)	1.28397 (13)	0.0165 (4)
C2	0.41893 (18)	0.15203 (17)	1.24064 (13)	0.0168 (4)
H2	0.3164	0.1840	1.2260	0.020*
C13	0.29072 (19)	0.23372 (17)	0.69990 (13)	0.0158 (4)
C24	0.1355 (2)	0.7643 (2)	0.54549 (16)	0.0276 (4)
H24	0.1890	0.8039	0.4965	0.033*
C19	0.7036 (2)	0.36195 (19)	0.74194 (17)	0.0255 (4)
H19	0.6584	0.3173	0.7941	0.031*
C18	0.6222 (2)	0.48502 (19)	0.68668 (15)	0.0210 (4)
C16	0.8424 (2)	0.4795 (2)	0.59447 (15)	0.0258 (4)
H16	0.8900	0.5217	0.5423	0.031*
O8	0.0714 (2)	0.5806 (2)	1.07599 (16)	0.0619 (6)
C25	−0.0156 (2)	0.8235 (2)	0.54958 (15)	0.0264 (4)
H25	−0.0638	0.9030	0.5015	0.032*
C12	0.44436 (19)	0.18089 (17)	0.69429 (13)	0.0156 (4)
C21	0.4599 (2)	0.5530 (2)	0.70361 (16)	0.0255 (4)
H21A	0.4416	0.6367	0.7205	0.031*
H21B	0.4279	0.5006	0.7640	0.031*
C4	0.62345 (19)	0.08341 (18)	1.36419 (14)	0.0183 (4)
H4	0.6574	0.0696	1.4340	0.022*
C1	0.52050 (18)	0.12908 (16)	1.16121 (13)	0.0145 (3)
C20	0.8513 (2)	0.3042 (2)	0.72098 (17)	0.0274 (4)
H20	0.9055	0.2200	0.7604	0.033*
C23	0.2086 (2)	0.6472 (2)	0.61279 (16)	0.0249 (4)
C17	0.6946 (2)	0.5442 (2)	0.61109 (15)	0.0252 (4)
H17	0.6431	0.6285	0.5709	0.030*
C31	0.1918 (3)	0.4644 (3)	1.0637 (3)	0.0607 (9)
H31A	0.2457	0.4196	1.1317	0.073*
H31B	0.1535	0.4062	1.0420	0.073*
C29	0.0880 (4)	0.6850 (3)	0.9999 (2)	0.0539 (7)
H29A	0.0693	0.7589	1.0324	0.065*
H29B	0.0176	0.7131	0.9402	0.065*
C27	0.1242 (2)	0.5970 (2)	0.68416 (19)	0.0364 (5)
H27	0.1694	0.5176	0.7331	0.044*
C26	−0.0260 (2)	0.6629 (2)	0.68382 (18)	0.0361 (5)
H26	−0.0819	0.6268	0.7335	0.043*
C22	0.3713 (2)	0.5746 (2)	0.60497 (18)	0.0354 (5)
H22A	0.4086	0.6224	0.5444	0.043*
H22B	0.3879	0.4900	0.5904	0.043*
C32	0.2865 (5)	0.4942 (3)	0.9878 (4)	0.112 (2)
H32A	0.2799	0.4646	0.9237	0.134*
H32B	0.3892	0.4511	1.0150	0.134*
H1O	0.287 (3)	0.170 (3)	1.405 (2)	0.055 (8)*
H5O	0.447 (3)	0.165 (2)	0.559 (2)	0.041 (7)*
H4O	0.881 (3)	0.032 (3)	0.934 (2)	0.050 (8)*
H6O	0.117 (3)	0.294 (3)	0.623 (2)	0.046 (8)*
H2O	0.910 (3)	0.015 (3)	1.244 (3)	0.063 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O6	0.0158 (6)	0.0376 (8)	0.0106 (6)	−0.0082 (6)	0.0020 (5)	−0.0076 (5)
O2	0.0103 (6)	0.0401 (8)	0.0128 (6)	−0.0040 (6)	−0.0008 (5)	−0.0057 (6)
O4	0.0101 (6)	0.0356 (8)	0.0110 (6)	−0.0046 (6)	0.0015 (5)	−0.0063 (5)
O5	0.0109 (6)	0.0241 (7)	0.0091 (6)	−0.0038 (5)	0.0008 (4)	−0.0047 (5)
O3	0.0103 (6)	0.0320 (7)	0.0141 (6)	−0.0042 (5)	0.0012 (5)	−0.0048 (5)
O1	0.0113 (6)	0.0344 (8)	0.0108 (6)	−0.0037 (6)	0.0022 (5)	−0.0063 (5)
O7	0.0119 (6)	0.0338 (8)	0.0120 (6)	−0.0036 (6)	−0.0022 (5)	−0.0048 (5)
N2	0.0149 (7)	0.0376 (10)	0.0206 (8)	−0.0053 (7)	0.0007 (6)	−0.0082 (7)
N1	0.0155 (7)	0.0315 (9)	0.0215 (8)	−0.0055 (7)	−0.0003 (6)	−0.0097 (7)
C10	0.0145 (8)	0.0142 (8)	0.0122 (8)	−0.0050 (7)	0.0010 (6)	−0.0029 (6)
C6	0.0129 (8)	0.0175 (9)	0.0120 (8)	−0.0039 (7)	0.0010 (6)	−0.0026 (6)
C7	0.0121 (8)	0.0167 (8)	0.0155 (8)	−0.0041 (7)	0.0011 (6)	−0.0024 (7)
C14	0.0106 (8)	0.0220 (9)	0.0158 (8)	−0.0028 (7)	0.0016 (6)	−0.0052 (7)
C11	0.0124 (8)	0.0195 (9)	0.0127 (8)	−0.0057 (7)	0.0019 (6)	−0.0038 (7)
C8	0.0132 (8)	0.0173 (9)	0.0114 (8)	−0.0047 (7)	0.0028 (6)	−0.0028 (6)
C9	0.0137 (8)	0.0168 (8)	0.0107 (8)	−0.0058 (7)	0.0032 (6)	−0.0037 (6)
C28	0.101 (3)	0.0576 (19)	0.086 (2)	−0.056 (2)	0.064 (2)	−0.0430 (17)
C3	0.0144 (8)	0.0214 (9)	0.0119 (8)	−0.0050 (7)	0.0035 (6)	−0.0054 (7)
C15	0.0148 (8)	0.0195 (9)	0.0126 (8)	−0.0052 (7)	0.0037 (6)	−0.0053 (7)
C5	0.0114 (8)	0.0207 (9)	0.0145 (8)	−0.0035 (7)	0.0001 (6)	−0.0033 (7)
C2	0.0100 (8)	0.0225 (9)	0.0148 (8)	−0.0027 (7)	0.0009 (6)	−0.0049 (7)
C13	0.0141 (8)	0.0182 (9)	0.0125 (8)	−0.0036 (7)	−0.0018 (6)	−0.0027 (7)
C24	0.0218 (10)	0.0421 (13)	0.0203 (10)	−0.0137 (9)	0.0028 (8)	−0.0074 (9)
C19	0.0197 (9)	0.0253 (10)	0.0318 (11)	−0.0106 (8)	0.0031 (8)	−0.0040 (8)
C18	0.0148 (8)	0.0267 (10)	0.0218 (9)	−0.0061 (8)	0.0008 (7)	−0.0090 (8)
C16	0.0174 (9)	0.0343 (11)	0.0214 (9)	−0.0079 (8)	0.0041 (7)	−0.0030 (8)
O8	0.0713 (14)	0.0642 (14)	0.0583 (13)	−0.0344 (12)	0.0352 (11)	−0.0242 (10)
C25	0.0204 (9)	0.0335 (11)	0.0208 (9)	−0.0061 (9)	−0.0028 (7)	−0.0037 (8)
C12	0.0152 (8)	0.0187 (9)	0.0118 (8)	−0.0057 (7)	0.0028 (6)	−0.0036 (7)
C21	0.0144 (9)	0.0328 (11)	0.0258 (10)	−0.0046 (8)	0.0026 (7)	−0.0089 (8)
C4	0.0160 (8)	0.0260 (10)	0.0108 (8)	−0.0055 (7)	−0.0009 (6)	−0.0043 (7)
C1	0.0149 (8)	0.0172 (9)	0.0101 (8)	−0.0051 (7)	−0.0010 (6)	−0.0022 (6)
C20	0.0207 (9)	0.0228 (10)	0.0335 (11)	−0.0040 (8)	−0.0016 (8)	−0.0038 (8)
C23	0.0145 (9)	0.0347 (11)	0.0240 (10)	−0.0039 (8)	−0.0010 (7)	−0.0132 (8)
C17	0.0195 (9)	0.0260 (10)	0.0216 (9)	−0.0029 (8)	0.0011 (7)	−0.0001 (8)
C31	0.0468 (16)	0.0524 (18)	0.0654 (19)	−0.0163 (14)	0.0168 (14)	0.0105 (14)
C29	0.072 (2)	0.0493 (16)	0.0474 (16)	−0.0313 (15)	0.0171 (14)	−0.0141 (13)
C27	0.0240 (11)	0.0312 (12)	0.0443 (14)	−0.0076 (9)	−0.0026 (9)	0.0051 (10)
C26	0.0217 (10)	0.0437 (14)	0.0361 (12)	−0.0127 (10)	0.0029 (9)	0.0036 (10)
C22	0.0149 (9)	0.0527 (15)	0.0334 (12)	−0.0014 (10)	−0.0005 (8)	−0.0198 (11)
C32	0.123 (3)	0.060 (2)	0.182 (5)	−0.061 (2)	0.117 (4)	−0.071 (3)

Geometric parameters (Å, º)

O6—C12	1.370 (2)	C5—C4	1.375 (2)
O6—H5O	0.86 (3)	C2—C1	1.385 (2)
O2—C5	1.352 (2)	C2—H2	0.9500
O2—H2O	0.87 (3)	C13—C12	1.401 (2)
O4—C8	1.358 (2)	C24—C25	1.381 (3)
O4—H4O	0.84 (3)	C24—C23	1.381 (3)
O5—C1	1.359 (2)	C24—H24	0.9500
O5—C9	1.3753 (19)	C19—C20	1.384 (3)
O3—C7	1.266 (2)	C19—C18	1.383 (3)
O1—C3	1.347 (2)	C19—H19	0.9500
O1—H1O	0.90 (3)	C18—C17	1.385 (3)
O7—C13	1.355 (2)	C18—C21	1.511 (2)
O7—H6O	0.89 (3)	C16—C17	1.384 (3)
N2—C25	1.331 (3)	C16—H16	0.9500
N2—C26	1.332 (3)	O8—C29	1.431 (3)
N1—C16	1.334 (3)	O8—C31	1.441 (4)
N1—C20	1.338 (3)	C25—H25	0.9500
C10—C15	1.400 (2)	C21—C22	1.526 (3)
C10—C11	1.407 (2)	C21—H21A	0.9900
C10—C9	1.462 (2)	C21—H21B	0.9900
C6—C1	1.396 (2)	C4—H4	0.9500
C6—C5	1.421 (2)	C20—H20	0.9500
C6—C7	1.429 (2)	C23—C27	1.384 (3)
C7—C8	1.436 (2)	C23—C22	1.504 (3)
C14—C15	1.377 (2)	C17—H17	0.9500
C14—C13	1.394 (2)	C31—C32	1.389 (4)
C14—H14	0.9500	C31—H31A	0.9900
C11—C12	1.378 (2)	C31—H31B	0.9900
C11—H11	0.9500	C29—H29A	0.9900
C8—C9	1.370 (2)	C29—H29B	0.9900
C28—C29	1.492 (4)	C27—C26	1.378 (3)
C28—C32	1.497 (4)	C27—H27	0.9500
C28—H28A	0.9900	C26—H26	0.9500
C28—H28B	0.9900	C22—H22A	0.9900
C3—C2	1.391 (2)	C22—H22B	0.9900
C3—C4	1.403 (2)	C32—H32A	0.9900
C15—H15	0.9500	C32—H32B	0.9900
C12—O6—H5O	107.2 (18)	N1—C16—H16	118.3
C5—O2—H2O	105 (2)	C17—C16—H16	118.3
C8—O4—H4O	106.0 (19)	C29—O8—C31	107.6 (2)
C1—O5—C9	122.16 (13)	N2—C25—C24	123.21 (19)
C3—O1—H1O	111.2 (18)	N2—C25—H25	118.4