research papers
Combinatorial selection of molecular conformations and supramolecular synthons in quercetin cocrystal landscapes: a route to ternary solids
aSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India
*Correspondence e-mail: desiraju@sscu.iisc.ernet.in
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
and synthon structure led to an increase in the energetic and structural space around the crystallization event. This space is the 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 in this study highlights the selectivity in conformation and synthon choice from the virtual combinatorial library in solution.1. Introduction
; 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 in organic compounds, especially if small changes in experimental conditions result (Nangia, 2008). This 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, 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).
(Groth, 1906–1919The concept of 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 can also involve changes in the main synthons themselves (Desiraju, 1995), the so-called synthon (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 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).
is very well studied in single component systems but systematic exploration of cocrystal has only recently begun in the crystal engineering context (AitipamulaQuercetin (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 (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 data integration and data reduction were carried out using the SAINT-Plus program. Crystal structures were solved by 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 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.
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 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 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 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 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 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.
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 so selectivity in synthon choice is clearly present. The crystallographic details of the crystal structures are given in the supporting information .
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.
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 (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 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).
We also conceptualized the role of anthracene (ANT) as a template molecule and obtained the respective 2:2:1 ternary solid (Fig. 9). This 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.
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
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 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
10.1107/S2052252515009884/lc5063sup1.cif
contains datablocks QTMP_I, QTMP_II, QTMP_III, QTMP_IV, QBP_I, QBP_II, QBP_III, QBP_IV, QDP_I, QDP_II, QDP_III, QDP_IV, QDP_V, QDPE_I, QDPE_II, QDPE_III, QAP_1, QAP_II, QPH_I, QPH_II, QPH_III, QPH_IV, QPH_V, QBP_22TP, QBP_TTF, QDP_22TP, QDP_PYR, QDP_ANT. DOI:Supporting figures and tables. DOI: 10.1107/S2052252515009884/lc5063sup2.pdf
For all compounds, program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013).
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) Å3 | 0.45 × 0.25 × 0.20 mm |
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 on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.058 | w = 1/[σ2(Fo2) + (0.0535P)2 + 0.2309P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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) |
C39H46N6O7 | V = 1826.6 (5) Å3 |
Mr = 710.82 | Z = 2 |
Monoclinic, Pc | Mo Kα radiation |
a = 9.0760 (13) Å | µ = 0.09 mm−1 |
b = 8.9616 (13) Å | T = 150 K |
c = 22.501 (3) Å | 0.45 × 0.25 × 0.20 mm |
β = 93.554 (7)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 8351 independent reflections |
Tmin = 0.728, Tmax = 1.000 | 6243 reflections with I > 2σ(I) |
18413 measured reflections | Rint = 0.062 |
R[F2 > 2σ(F2)] = 0.058 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.130 | Δρmax = 0.25 e Å−3 |
S = 1.04 | Δρmin = −0.27 e Å−3 |
8351 reflections | Absolute structure: Flack x determined using 2448 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). |
489 parameters | Absolute structure parameter: 0.5 (8) |
2 restraints |
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. |
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.45 × 0.40 × 0.12 mm |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.163 | w = 1/[σ2(Fo2) + (0.0734P)2 + 1.8069P] where P = (Fo2 + 2Fc2)/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 |
C31H34N4O7 | V = 2885.7 (7) Å3 |
Mr = 574.62 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.831 (2) Å | µ = 0.10 mm−1 |
b = 9.3122 (13) Å | T = 150 K |
c = 20.211 (3) Å | 0.45 × 0.40 × 0.12 mm |
β = 104.415 (7)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 6558 independent reflections |
Tmin = 0.821, Tmax = 1.000 | 4018 reflections with I > 2σ(I) |
22578 measured reflections | Rint = 0.077 |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.163 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.32 e Å−3 |
6558 reflections | Δρmin = −0.33 e Å−3 |
399 parameters |
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. |
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
C27H30N2O9 | V = 1274.26 (17) Å3 |
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 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.159 | w = 1/[σ2(Fo2) + (0.0967P)2 + 0.5735P] where P = (Fo2 + 2Fc2)/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 |
C27H30N2O9 | γ = 81.580 (6)° |
Mr = 526.53 | V = 1274.26 (17) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.3506 (7) Å | Mo Kα radiation |
b = 10.9120 (8) Å | µ = 0.10 mm−1 |
c = 13.002 (1) Å | T = 150 K |
α = 76.798 (5)° | 0.40 × 0.40 × 0.15 mm |
β = 84.048 (6)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 5832 independent reflections |
Tmin = 0.752, Tmax = 1.000 | 4470 reflections with I > 2σ(I) |
13650 measured reflections | Rint = 0.034 |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.159 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | Δρmax = 0.29 e Å−3 |
5832 reflections | Δρmin = −0.39 e Å−3 |
363 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
C27H30N2O8 | V = 1266.0 (2) Å3 |
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 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.202 | w = 1/[σ2(Fo2) + (0.102P)2 + 1.1876P] where P = (Fo2 + 2Fc2)/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 |
C27H30N2O8 | γ = 82.377 (6)° |
Mr = 510.53 | V = 1266.0 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.3202 (10) Å | Mo Kα radiation |
b = 10.7538 (12) Å | µ = 0.10 mm−1 |
c = 12.9869 (14) Å | T = 150 K |
α = 79.471 (6)° | 0.60 × 0.40 × 0.15 mm |
β = 85.133 (6)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 5779 independent reflections |
Tmin = 0.844, Tmax = 1.000 | 4277 reflections with I > 2σ(I) |
13412 measured reflections | Rint = 0.030 |
R[F2 > 2σ(F2)] = 0.070 | 0 restraints |
wR(F2) = 0.202 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.80 e Å−3 |
5779 reflections | Δρmin = −0.62 e Å−3 |
354 parameters |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—C28i | 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—C27i | 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—O8i | 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—C29i | 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—C28i | 124.3 (18) | C14—C13—C12 | 119.16 (19) |
C26—C27—H27A | 106.2 | C13—C14—C15 | 120.7 (2) |
C28i—C27—H27A | 106.2 | C13—C14—H14 | 119.7 |
C26—C27—H27B | 106.2 | C15—C14—H14 | 119.7 |
C28i—C27—H27B | 106.2 | C14—C15—C10 | 120.8 (2) |
H27A—C27—H27B | 106.4 | C14—C15—H15 | 119.6 |
C27i—C28—C29 | 105.4 (9) | C10—C15—H15 | 119.6 |
C27i—C28—H28A | 110.7 | N1—C16—C17 | 120.4 (2) |
C29—C28—H28A | 110.7 | N1—C16—C23 | 117.4 (2) |
C27i—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—O8i | 94.9 (7) | C16—C17—C24 | 123.1 (2) |
C28—C29—H29A | 112.8 | N2—C18—C19 | 120.2 (2) |
O8i—C29—H29A | 112.8 | N2—C18—C20 | 117.3 (2) |
C28—C29—H29B | 112.8 | C19—C18—C20 | 122.5 (2) |
O8i—C29—H29B | 112.8 | N1—C19—C18 | 119.9 (2) |
H29A—C29—H29B | 110.2 | N1—C19—C22 | 117.0 (2) |
C26—O8—C29i | 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. |
C29H26N2O9 | V = 1268.29 (17) Å3 |
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 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0579P)2 + 0.5172P] where P = (Fo2 + 2Fc2)/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 |
C29H26N2O9 | γ = 106.846 (7)° |
Mr = 546.52 | V = 1268.29 (17) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.8334 (7) Å | Mo Kα radiation |
b = 10.7098 (8) Å | µ = 0.11 mm−1 |
c = 13.0790 (9) Å | T = 150 K |
α = 102.815 (7)° | 1.00 × 0.50 × 0.20 mm |
β = 95.031 (7)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 5791 independent reflections |
Tmin = 0.898, Tmax = 1.000 | 5160 reflections with I > 2σ(I) |
13454 measured reflections | Rint = 0.016 |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.34 e Å−3 |
5791 reflections | Δρmin = −0.23 e Å−3 |
381 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
C29H18N2O8 | V = 1271.6 (5) Å3 |
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 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.075 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.214 | w = 1/[σ2(Fo2) + (0.103P)2 + 1.8694P] where P = (Fo2 + 2Fc2)/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 |
C29H18N2O8 | γ = 106.943 (7)° |
Mr = 522.45 | V = 1271.6 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.806 (2) Å | Mo Kα radiation |
b = 10.778 (2) Å | µ = 0.10 mm−1 |
c = 13.055 (3) Å | T = 150 K |
α = 102.833 (7)° | 0.60 × 0.30 × 0.25 mm |
β = 94.525 (7)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 4943 independent reflections |
Tmin = 0.741, Tmax = 1.000 | 3753 reflections with I > 2σ(I) |
10628 measured reflections | Rint = 0.037 |
R[F2 > 2σ(F2)] = 0.075 | 0 restraints |
wR(F2) = 0.214 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 1.14 e Å−3 |
4943 reflections | Δρmin = −0.90 e Å−3 |
372 parameters |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
C30H22N3O7 | V = 1277.0 (11) Å3 |
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 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0543P)2 + 0.4614P] where P = (Fo2 + 2Fc2)/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 |
C30H22N3O7 | γ = 107.947 (8)° |
Mr = 536.50 | V = 1277.0 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.844 (5) Å | Mo Kα radiation |
b = 10.636 (6) Å | µ = 0.10 mm−1 |
c = 13.071 (7) Å | T = 150 K |
α = 98.324 (7)° | 0.65 × 0.45 × 0.30 mm |
β = 94.601 (7)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 5767 independent reflections |
Tmin = 0.857, Tmax = 1.000 | 4834 reflections with I > 2σ(I) |
13246 measured reflections | Rint = 0.022 |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.34 e Å−3 |
5767 reflections | Δρmin = −0.21 e Å−3 |
381 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—C32i | 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—C32i | 122.51 (19) |
O5—C12—C11 | 118.67 (11) | C31—C32—C32i | 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. |
C45H36N6O8 | V = 1860.6 (4) Å3 |
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 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0836P)2 + 0.7989P] where P = (Fo2 + 2Fc2)/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 |
C45H36N6O8 | γ = 76.273 (5)° |
Mr = 788.80 | V = 1860.6 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.0222 (12) Å | Mo Kα radiation |
b = 12.8756 (16) Å | µ = 0.10 mm−1 |
c = 15.0597 (18) Å | T = 150 K |
α = 81.685 (6)° | 0.65 × 0.50 × 0.25 mm |
β = 83.118 (6)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 8502 independent reflections |
Tmin = 0.804, Tmax = 1.000 | 6720 reflections with I > 2σ(I) |
19338 measured reflections | Rint = 0.031 |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.134 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.88 | Δρmax = 0.31 e Å−3 |
8502 reflections | Δρmin = −0.21 e Å−3 |
560 parameters |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
C31H28N2O9 | V = 1367.8 (2) Å3 |
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 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0598P)2 + 0.4848P] where P = (Fo2 + 2Fc2)/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 |
C31H28N2O9 | γ = 115.237 (8)° |
Mr = 572.55 | V = 1367.8 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.1899 (9) Å | Mo Kα radiation |
b = 11.6532 (11) Å | µ = 0.10 mm−1 |
c = 13.0214 (12) Å | T = 150 K |
α = 97.351 (7)° | 0.50 × 0.25 × 0.15 mm |
β = 95.446 (7)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 6248 independent reflections |
Tmin = 0.818, Tmax = 1.000 | 4498 reflections with I > 2σ(I) |
14650 measured reflections | Rint = 0.035 |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.28 e Å−3 |
6248 reflections | Δρmin = −0.23 e Å−3 |
407 parameters |
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. |
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
C31H28N2O8 | V = 1340.13 (17) Å3 |
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 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.162 | w = 1/[σ2(Fo2) + (0.0802P)2 + 0.6053P] where P = (Fo2 + 2Fc2)/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 |
C31H28N2O8 | γ = 65.573 (5)° |
Mr = 556.55 | V = 1340.13 (17) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.0381 (7) Å | Mo Kα radiation |
b = 11.5707 (8) Å | µ = 0.10 mm−1 |
c = 13.0194 (9) Å | T = 293 K |
α = 76.744 (5)° | 0.40 × 0.20 × 0.20 mm |
β = 84.502 (6)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 6106 independent reflections |
Tmin = 0.794, Tmax = 1.000 | 4337 reflections with I > 2σ(I) |
14382 measured reflections | Rint = 0.034 |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.48 e Å−3 |
6106 reflections | Δρmin = −0.48 e Å−3 |
398 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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 |
C30H26N3O8 | V = 1322.2 (4) Å3 |
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 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.178 | w = 1/[σ2(Fo2) + (0.0779P)2 + 0.8181P] where P = (Fo2 + 2Fc2)/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 |
C30H26N3O8 | γ = 66.082 (5)° |
Mr = 556.54 | V = 1322.2 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.9867 (15) Å | Mo Kα radiation |
b = 11.2949 (17) Å | µ = 0.10 mm−1 |
c = 13.040 (2) Å | T = 150 K |
α = 79.558 (6)° | 0.40 × 0.20 × 0.12 mm |
β = 85.192 (6)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 6040 independent reflections |
Tmin = 0.747, Tmax = 1.000 | 3745 reflections with I > 2σ(I) |
13781 measured reflections | Rint = 0.052 |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.178 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.49 e Å−3 |
6040 reflections | Δρmin = −0.41 e Å−3 |
400 parameters |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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···O2i | 0.95 | 2.47 | 3.325 (3) | 150 |
C16—H16···O8ii | 0.95 | 2.32 | 3.202 (4) | 155 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z. |
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) Å3 | 0.30 × 0.20 × 0.15 mm |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0488P)2 + 1.7932P] where P = (Fo2 + 2Fc2)/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 |
C39H30N4O7 | V = 3165.5 (3) Å3 |
Mr = 666.67 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.0656 (11) Å | µ = 0.10 mm−1 |
b = 11.6584 (6) Å | T = 150 K |
c = 16.661 (1) Å | 0.30 × 0.20 × 0.15 mm |
β = 115.565 (2)° |
Absorption correction: analytical Bruker, AXS, 2008 | 7197 independent reflections |
Tmin = 0.977, Tmax = 0.985 | 5739 reflections with I > 2σ(I) |
27138 measured reflections | Rint = 0.038 |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.68 e Å−3 |
7197 reflections | Δρmin = −0.44 e Å−3 |
497 parameters |
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. |
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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 |
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···O5i | 0.95 | 2.52 | 3.339 (2) | 145 |
C37—H37···O3ii | 0.95 | 2.41 | 3.014 (2) | 121 |
C38—H38···O6iii | 0.95 | 2.61 | 3.364 (2) | 137 |
O6—H6O···N1iv | 0.96 (2) | 1.80 (2) | 2.7588 (17) | 173 (2) |
O5—H5O···N3v | 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···N4ii | 0.91 (3) | 1.81 (3) | 2.6920 (17) | 162 (2) |
O1—H1O···N2vi | 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. |
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) Å3 | 0.30 × 0.20 × 0.12 mm |
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 on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.0666P)2 + 1.7713P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0006 (2) |
C27H20N2O7 | V = 4376.0 (17) Å3 |
Mr = 484.45 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.831 (5) Å | µ = 0.11 mm−1 |
b = 12.904 (3) Å | T = 150 K |
c = 15.876 (4) Å | 0.30 × 0.20 × 0.12 mm |
β = 101.912 (7)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 5006 independent reflections |
Tmin = 0.777, Tmax = 1.000 | 3202 reflections with I > 2σ(I) |
18633 measured reflections | Rint = 0.071 |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.27 e Å−3 |
5006 reflections | Δρmin = −0.32 e Å−3 |
354 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N1i | 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···O5ii | 0.85 (3) | 1.90 (3) | 2.690 (2) | 153 (3) |
O5—H5O···O2iii | 0.97 (4) | 1.95 (4) | 2.797 (2) | 144 (3) |
O6—H6O···N2iv | 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···N1i | 0.95 | 2.59 | 3.287 (3) | 131 |
C11—H11···O4 | 0.95 | 2.15 | 2.821 (3) | 127 |
C20—H20···O3v | 0.95 | 2.58 | 3.294 (3) | 132 |
C24—H24···O4vi | 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. |
C31H30N2O8 | V = 1336.8 (2) Å3 |
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 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.148 | w = 1/[σ2(Fo2) + (0.0694P)2 + 0.7053P] where P = (Fo2 + 2Fc2)/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 |
C31H30N2O8 | γ = 67.035 (5)° |
Mr = 558.57 | V = 1336.8 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.8782 (8) Å | Mo Kα radiation |
b = 11.5881 (10) Å | µ = 0.10 mm−1 |
c = 13.041 (1) Å | T = 150 K |
α = 76.595 (5)° | 0.40 × 0.20 × 0.20 mm |
β = 85.792 (6)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 6112 independent reflections |
Tmin = 0.777, Tmax = 1.000 | 4658 reflections with I > 2σ(I) |
14292 measured reflections | Rint = 0.036 |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.44 e Å−3 |
6112 reflections | Δρmin = −0.41 e Å−3 |
390 parameters |
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. |
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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 |
C13—O7—H6O | 109.7 (17) | C24—C25—H25 | 118.4 |
C25—N2—C26 | 116.87 (17) | O6—C12—C11 | 118.71 (15) |
C16—N1—C20 | 116.85 (16) | O6—C12—C13 | 120.64 (15) |
C15—C10—C11 | 118.07 (15) | C11—C12—C13 | 120.65 (15) |
C15—C10—C9 | 119.26 (15) | C18—C21—C22 | 110.47 (16) |
C11—C10—C9 | 122.67 (15) | C18—C21—H21A | 109.6 |
C1—C6—C5 | 117.68 (15) | C22—C21—H21A | 109.6 |
C1—C6—C7 | 119.32 (15) | C18—C21—H21B | 109.6 |
C5—C6—C7 | 122.96 (15) | C22—C21—H21B | 109.6 |
O3—C7—C6 | 122.70 (16) | H21A—C21—H21B | 108.1 |
O3—C7—C8 | 120.08 (15) | C5—C4—C3 | 119.81 (16) |
C6—C7—C8 | 117.22 (15) | C5—C4—H4 | 120.1 |
C15—C14—C13 | 120.64 (16) | C3—C4—H4 | 120.1 |
C15—C14—H14 | 119.7 | O5—C1—C2 | 116.34 (15) |
C13—C14—H14 | 119.7 | O5—C1—C6 | 120.62 (15) |
C12—C11—C10 | 120.73 (16) | C2—C1—C6 | 123.04 (15) |
C12—C11—H11 | 119.6 | N1—C20—C19 | 123.22 (19) |
C10—C11—H11 | 119.6 | N1—C20—H20 | 118.4 |
O4—C8—C9 | 121.02 (15) | C19—C20—H20 | 118.4 |
O4—C8—C7 | 117.72 (15) | C24—C23—C27 | 116.91 (18) |
C9—C8—C7 | 121.25 (15) | C24—C23—C22 | 121.48 (19) |
C8—C9—O5 | 119.39 (15) | C27—C23—C22 | 121.5 (2) |
C8—C9—C10 | 129.68 (15) | C16—C17—C18 | 119.54 (18) |
O5—C9—C10 | 110.93 (14) | C16—C17—H17 | 120.2 |
C29—C28—C32 | 103.3 (2) | C18—C17—H17 | 120.2 |
C29—C28—H28A | 111.1 | C32—C31—O8 | 109.6 (3) |
C32—C28—H28A | 111.1 | C32—C31—H31A | 109.7 |
C29—C28—H28B | 111.1 | O8—C31—H31A | 109.7 |
C32—C28—H28B | 111.1 | C32—C31—H31B | 109.7 |
H28A—C28—H28B | 109.1 | O8—C31—H31B | 109.7 |
O1—C3—C2 | 121.92 (15) | H31A—C31—H31B | 108.2 |
O1—C3—C4 | 116.62 (15) | O8—C29—C28 | 106.9 (2) |
C2—C3—C4 | 121.45 (15) | O8—C29—H29A | 110.3 |
C14—C15—C10 | 121.12 (15) | C28—C29—H29A | 110.3 |
C14—C15—H15 | 119.4 | O8—C29—H29B | 110.3 |
C10—C15—H15 | 119.4 | C28—C29—H29B | 110.3 |
O2—C5—C4 | 119.87 (16) | H29A—C29—H29B | 108.6 |
O2—C5—C6 | 119.76 (15) | C26—C27—C23 | 119.6 (2) |
C4—C5—C6 | 120.37 (16) | C26—C27—H27 | 120.2 |
C1—C2—C3 | 117.61 (15) | C23—C27—H27 | 120.2 |
C1—C2—H2 | 121.2 | N2—C26—C27 | 123.6 (2) |
C3—C2—H2 | 121.2 | N2—C26—H26 | 118.2 |
O7—C13—C14 | 123.73 (15) | C27—C26—H26 | 118.2 |
O7—C13—C12 | 117.49 (15) | C23—C22—C21 | 114.23 (17) |
C14—C13—C12 | 118.79 (15) | C23—C22—H22A | 108.7 |
C25—C24—C23 | 119.85 (19) | C21—C22—H22A | 108.7 |
C25—C24—H24 | 120.1 | C23—C22—H22B | 108.7 |
C23—C24—H24 | 120.1 | C21—C22—H22B | 108.7 |
C20—C19—C18 | 119.73 (18) | H22A—C22—H22B | 107.6 |
C20—C19—H19 | 120.1 | C31—C32—C28 | 107.9 (3) |
C18—C19—H19 | 120.1 | C31—C32—H32A | 110.1 |
C19—C18—C17 | 117.18 (17) | C28—C32—H32A | 110.1 |
C19—C18—C21 | 122.65 (17) | C31—C32—H32B | 110.1 |
C17—C18—C21 | 120.14 (18) | C28—C32—H32B | 110.1 |
N1—C16—C17 | 123.47 (18) | H32A—C32—H32B | 108.4 |
C39H34N4O7 | Z = 4 |
Mr = 670.70 | F(000) = 1408 |
Monoclinic, P21/c | Dx = 1.350 Mg m−3 |
a = 20.028 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5025 (13) Å | µ = 0.09 mm−1 |
c = 16.5786 (18) Å | T = 150 K |
β = 108.851 (4)° | Plate, yellow |
V = 3300.2 (7) Å3 | 0.25 × 0.12 × 0.12 mm |
Absorption correction: analytical Bruker, AXS, 2008 | Rint = 0.053 |
Tmin = 0.987, Tmax = 0.989 | θmax = 27.5°, θmin = 2.2° |
36152 measured reflections | h = −26→26 |
7537 independent reflections | k = −13→13 |
5491 reflections with I > 2σ(I) | l = −21→18 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.7852P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
7537 reflections | Δρmax = 0.34 e Å−3 |
471 parameters | Δρmin = −0.29 e Å−3 |
C39H34N4O7 | V = 3300.2 (7) Å3 |
Mr = 670.70 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 20.028 (3) Å | µ = 0.09 mm−1 |
b = 10.5025 (13) Å | T = 150 K |
c = 16.5786 (18) Å | 0.25 × 0.12 × 0.12 mm |
β = 108.851 (4)° |
Absorption correction: analytical Bruker, AXS, 2008 | 7537 independent reflections |
Tmin = 0.987, Tmax = 0.989 | 5491 reflections with I > 2σ(I) |
36152 measured reflections | Rint = 0.053 |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.34 e Å−3 |
7537 reflections | Δρmin = −0.29 e Å−3 |
471 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
H5O | 0.0776 (10) | 0.3777 (19) | 0.0725 (12) | 0.047 (6)* | |
H1O | 0.5489 (10) | 0.9447 (19) | 0.2300 (13) | 0.049 (6)* | |
H6O | 0.1980 (11) | 0.3182 (19) | −0.1163 (12) | 0.047 (6)* | |
H4O | 0.2052 (11) | 0.6143 (19) | 0.3351 (13) | 0.053 (6)* | |
H2O | 0.3617 (12) | 0.872 (2) | 0.4555 (13) | 0.056 (7)* | |
O5 | 0.09687 (5) | 0.36156 (10) | 0.02625 (7) | 0.0200 (2) | |
O6 | 0.16927 (6) | 0.31870 (10) | −0.08138 (6) | 0.0205 (2) | |
O7 | 0.34248 (5) | 0.70865 (9) | 0.18679 (6) | 0.0170 (2) | |
O2 | 0.40115 (6) | 0.91754 (11) | 0.45725 (6) | 0.0231 (3) | |
O4 | 0.21364 (6) | 0.60002 (10) | 0.28236 (7) | 0.0232 (3) | |
O3 | 0.29216 (6) | 0.76989 (10) | 0.40245 (6) | 0.0228 (3) | |
O1 | 0.54386 (6) | 0.97279 (11) | 0.28250 (7) | 0.0265 (3) | |
C6 | 0.36882 (7) | 0.81006 (13) | 0.32285 (9) | 0.0147 (3) | |
C1 | 0.38471 (8) | 0.78593 (14) | 0.24814 (9) | 0.0153 (3) | |
C9 | 0.28646 (7) | 0.64448 (14) | 0.19883 (9) | 0.0150 (3) | |
C7 | 0.30877 (8) | 0.75049 (14) | 0.33635 (9) | 0.0158 (3) | |
C12 | 0.16063 (7) | 0.42017 (14) | 0.04314 (9) | 0.0152 (3) | |
C10 | 0.25490 (7) | 0.55817 (14) | 0.12691 (9) | 0.0145 (3) | |
C13 | 0.19880 (8) | 0.39614 (13) | −0.01336 (9) | 0.0153 (3) | |
C14 | 0.26482 (8) | 0.45031 (14) | 0.00251 (9) | 0.0162 (3) | |
H14 | 0.2913 | 0.4321 | −0.0345 | 0.019* | |
C15 | 0.29295 (8) | 0.53053 (14) | 0.07142 (9) | 0.0160 (3) | |
H15 | 0.3383 | 0.5670 | 0.0811 | 0.019* | |
C8 | 0.26823 (8) | 0.66364 (14) | 0.27077 (9) | 0.0164 (3) | |
C11 | 0.18861 (7) | 0.50107 (14) | 0.11192 (9) | 0.0151 (3) | |
H11 | 0.1625 | 0.5181 | 0.1495 | 0.018* | |
C3 | 0.48613 (8) | 0.91929 (15) | 0.29279 (9) | 0.0190 (3) | |
C4 | 0.47216 (8) | 0.94671 (14) | 0.36874 (9) | 0.0182 (3) | |
H4 | 0.5023 | 1.0023 | 0.4097 | 0.022* | |
C5 | 0.41471 (8) | 0.89281 (14) | 0.38355 (9) | 0.0168 (3) | |
C2 | 0.44214 (8) | 0.83915 (14) | 0.23133 (9) | 0.0182 (3) | |
H2 | 0.4512 | 0.8216 | 0.1796 | 0.022* | |
N1 | 0.24156 (7) | 0.17089 (13) | 0.30501 (8) | 0.0225 (3) | |
N2 | 0.43638 (7) | 0.09262 (13) | −0.13458 (8) | 0.0249 (3) | |
C19 | 0.28950 (8) | 0.25042 (16) | 0.19980 (10) | 0.0234 (4) | |
H19 | 0.3071 | 0.3212 | 0.1772 | 0.028* | |
C23 | 0.40326 (8) | 0.13234 (16) | 0.01593 (10) | 0.0212 (3) | |
C18 | 0.28786 (8) | 0.13041 (15) | 0.16370 (9) | 0.0191 (3) | |
C17 | 0.26336 (8) | 0.03077 (16) | 0.20190 (9) | 0.0212 (3) | |
H17 | 0.2615 | −0.0533 | 0.1802 | 0.025* | |
C21 | 0.30955 (8) | 0.10965 (15) | 0.08564 (9) | 0.0218 (3) | |
H21A | 0.2767 | 0.1567 | 0.0372 | 0.026* | |
H21B | 0.3052 | 0.0180 | 0.0710 | 0.026* | |
C20 | 0.26546 (8) | 0.26685 (16) | 0.26873 (10) | 0.0236 (4) | |
H20 | 0.2660 | 0.3501 | 0.2913 | 0.028* | |
C27 | 0.40492 (8) | 0.01056 (16) | −0.01669 (10) | 0.0255 (4) | |
H27 | 0.3943 | −0.0615 | 0.0115 | 0.031* | |
C22 | 0.38524 (8) | 0.15279 (17) | 0.09678 (10) | 0.0251 (4) | |
H22A | 0.3903 | 0.2442 | 0.1122 | 0.030* | |
H22B | 0.4186 | 0.1042 | 0.1439 | 0.030* | |
C16 | 0.24177 (8) | 0.05511 (16) | 0.27171 (10) | 0.0226 (4) | |
H16 | 0.2262 | −0.0146 | 0.2975 | 0.027* | |
C26 | 0.42219 (8) | −0.00469 (16) | −0.09055 (10) | 0.0262 (4) | |
H26 | 0.4241 | −0.0886 | −0.1110 | 0.031* | |
C24 | 0.41832 (8) | 0.23347 (16) | −0.02962 (10) | 0.0232 (4) | |
H24 | 0.4178 | 0.3184 | −0.0101 | 0.028* | |
C25 | 0.43408 (8) | 0.20966 (16) | −0.10354 (10) | 0.0260 (4) | |
H25 | 0.4438 | 0.2801 | −0.1339 | 0.031* | |
N3 | 0.17263 (7) | 0.60365 (13) | 0.41831 (8) | 0.0236 (3) | |
N4 | −0.03571 (7) | 0.61881 (13) | 0.85100 (8) | 0.0238 (3) | |
C30 | 0.10970 (8) | 0.57395 (15) | 0.54652 (9) | 0.0206 (3) | |
C29 | 0.11855 (8) | 0.47066 (15) | 0.49780 (9) | 0.0208 (3) | |
H29 | 0.1039 | 0.3878 | 0.5078 | 0.025* | |
C28 | 0.14886 (8) | 0.49051 (15) | 0.43481 (10) | 0.0218 (3) | |
H28 | 0.1531 | 0.4197 | 0.4012 | 0.026* | |
C35 | 0.03594 (8) | 0.65251 (16) | 0.73199 (10) | 0.0228 (4) | |
C37 | 0.02418 (9) | 0.55765 (19) | 0.85864 (11) | 0.0338 (4) | |
H37 | 0.0427 | 0.5019 | 0.9057 | 0.041* | |
C36 | 0.06090 (10) | 0.57139 (19) | 0.80120 (11) | 0.0384 (5) | |
H36 | 0.1033 | 0.5251 | 0.8093 | 0.046* | |
C31 | 0.13414 (9) | 0.69085 (17) | 0.52930 (10) | 0.0295 (4) | |
H31 | 0.1294 | 0.7639 | 0.5608 | 0.035* | |
C39 | −0.02673 (9) | 0.71313 (17) | 0.72341 (11) | 0.0295 (4) | |
H39 | −0.0470 | 0.7679 | 0.6763 | 0.035* | |
C38 | −0.06036 (9) | 0.69436 (18) | 0.78348 (11) | 0.0325 (4) | |
H38 | −0.1035 | 0.7379 | 0.7760 | 0.039* | |
C33 | 0.07507 (8) | 0.55544 (16) | 0.61466 (10) | 0.0241 (4) | |
H33A | 0.1000 | 0.4862 | 0.6532 | 0.029* | |
H33B | 0.0258 | 0.5273 | 0.5868 | 0.029* | |
C34 | 0.07432 (10) | 0.67310 (17) | 0.66812 (11) | 0.0299 (4) | |
H34A | 0.1236 | 0.6986 | 0.6989 | 0.036* | |
H34B | 0.0515 | 0.7439 | 0.6297 | 0.036* | |
C32 | 0.16557 (9) | 0.70160 (16) | 0.46604 (10) | 0.0297 (4) | |
H32 | 0.1828 | 0.7825 | 0.4564 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O5 | 0.0181 (5) | 0.0259 (6) | 0.0185 (5) | −0.0068 (5) | 0.0094 (5) | −0.0036 (5) |
O6 | 0.0225 (6) | 0.0253 (6) | 0.0156 (5) | −0.0078 (5) | 0.0089 (5) | −0.0077 (4) |
O7 | 0.0178 (5) | 0.0217 (6) | 0.0137 (5) | −0.0065 (5) | 0.0080 (4) | −0.0050 (4) |
O2 | 0.0258 (6) | 0.0300 (7) | 0.0168 (5) | −0.0048 (5) | 0.0115 (5) | −0.0088 (5) |
O4 | 0.0264 (6) | 0.0304 (7) | 0.0186 (6) | −0.0103 (5) | 0.0154 (5) | −0.0070 (5) |
O3 | 0.0270 (6) | 0.0282 (6) | 0.0178 (5) | −0.0044 (5) | 0.0136 (5) | −0.0066 (5) |
O1 | 0.0237 (6) | 0.0358 (7) | 0.0233 (6) | −0.0127 (5) | 0.0120 (5) | −0.0106 (5) |
C6 | 0.0163 (7) | 0.0142 (7) | 0.0141 (7) | 0.0023 (6) | 0.0054 (6) | 0.0006 (6) |
C1 | 0.0164 (7) | 0.0146 (7) | 0.0129 (7) | 0.0005 (6) | 0.0021 (6) | −0.0014 (6) |
C9 | 0.0138 (7) | 0.0160 (8) | 0.0157 (7) | −0.0001 (6) | 0.0053 (6) | 0.0010 (6) |
C7 | 0.0186 (8) | 0.0158 (8) | 0.0139 (7) | 0.0044 (6) | 0.0065 (6) | 0.0010 (6) |
C12 | 0.0144 (7) | 0.0163 (8) | 0.0149 (7) | −0.0003 (6) | 0.0049 (6) | 0.0026 (6) |
C10 | 0.0179 (7) | 0.0149 (7) | 0.0109 (7) | 0.0004 (6) | 0.0049 (6) | 0.0013 (6) |
C13 | 0.0194 (8) | 0.0149 (8) | 0.0112 (7) | −0.0012 (6) | 0.0045 (6) | −0.0005 (6) |
C14 | 0.0196 (8) | 0.0186 (8) | 0.0129 (7) | 0.0003 (6) | 0.0088 (6) | −0.0002 (6) |
C15 | 0.0160 (7) | 0.0183 (8) | 0.0149 (7) | −0.0021 (6) | 0.0068 (6) | 0.0015 (6) |
C8 | 0.0171 (7) | 0.0179 (8) | 0.0162 (7) | 0.0014 (6) | 0.0080 (6) | 0.0016 (6) |
C11 | 0.0175 (7) | 0.0170 (8) | 0.0129 (7) | 0.0015 (6) | 0.0078 (6) | 0.0011 (6) |
C3 | 0.0161 (7) | 0.0219 (8) | 0.0194 (8) | −0.0009 (7) | 0.0064 (6) | 0.0002 (6) |
C4 | 0.0191 (8) | 0.0190 (8) | 0.0145 (7) | −0.0007 (6) | 0.0023 (6) | −0.0034 (6) |
C5 | 0.0199 (8) | 0.0180 (8) | 0.0127 (7) | 0.0035 (6) | 0.0056 (6) | −0.0007 (6) |
C2 | 0.0187 (8) | 0.0228 (8) | 0.0146 (7) | −0.0024 (7) | 0.0074 (6) | −0.0035 (6) |
N1 | 0.0219 (7) | 0.0291 (8) | 0.0194 (7) | 0.0068 (6) | 0.0106 (6) | 0.0082 (6) |
N2 | 0.0219 (7) | 0.0313 (8) | 0.0242 (7) | −0.0093 (6) | 0.0114 (6) | −0.0089 (6) |
C19 | 0.0279 (9) | 0.0245 (9) | 0.0210 (8) | 0.0034 (7) | 0.0122 (7) | 0.0068 (7) |
C23 | 0.0161 (8) | 0.0278 (9) | 0.0210 (8) | −0.0032 (7) | 0.0075 (7) | −0.0047 (7) |
C18 | 0.0156 (8) | 0.0252 (9) | 0.0161 (7) | 0.0052 (7) | 0.0046 (6) | 0.0053 (6) |
C17 | 0.0175 (8) | 0.0245 (9) | 0.0211 (8) | 0.0045 (7) | 0.0058 (6) | 0.0045 (7) |
C21 | 0.0229 (8) | 0.0260 (9) | 0.0184 (8) | 0.0005 (7) | 0.0091 (7) | 0.0010 (7) |
C20 | 0.0277 (9) | 0.0248 (9) | 0.0205 (8) | 0.0059 (7) | 0.0107 (7) | 0.0035 (7) |
C27 | 0.0247 (9) | 0.0257 (9) | 0.0294 (9) | −0.0059 (7) | 0.0132 (7) | −0.0019 (7) |
C22 | 0.0233 (9) | 0.0332 (10) | 0.0208 (8) | −0.0006 (7) | 0.0099 (7) | −0.0029 (7) |
C16 | 0.0195 (8) | 0.0254 (9) | 0.0244 (8) | 0.0019 (7) | 0.0091 (7) | 0.0087 (7) |
C26 | 0.0249 (9) | 0.0256 (9) | 0.0318 (9) | −0.0088 (7) | 0.0146 (7) | −0.0124 (7) |
C24 | 0.0212 (8) | 0.0242 (9) | 0.0250 (8) | −0.0029 (7) | 0.0085 (7) | −0.0055 (7) |
C25 | 0.0266 (9) | 0.0277 (9) | 0.0266 (9) | −0.0068 (7) | 0.0127 (7) | −0.0015 (7) |
N3 | 0.0273 (7) | 0.0265 (8) | 0.0210 (7) | −0.0046 (6) | 0.0136 (6) | −0.0037 (6) |
N4 | 0.0207 (7) | 0.0329 (8) | 0.0207 (7) | −0.0025 (6) | 0.0107 (6) | −0.0027 (6) |
C30 | 0.0168 (8) | 0.0288 (9) | 0.0171 (7) | −0.0038 (7) | 0.0066 (6) | −0.0007 (7) |
C29 | 0.0200 (8) | 0.0194 (8) | 0.0236 (8) | −0.0017 (7) | 0.0078 (7) | 0.0018 (7) |
C28 | 0.0209 (8) | 0.0231 (9) | 0.0225 (8) | −0.0006 (7) | 0.0085 (7) | −0.0038 (7) |
C35 | 0.0256 (9) | 0.0267 (9) | 0.0194 (8) | −0.0013 (7) | 0.0119 (7) | −0.0010 (7) |
C37 | 0.0280 (9) | 0.0514 (12) | 0.0253 (9) | 0.0111 (9) | 0.0134 (8) | 0.0139 (8) |
C36 | 0.0302 (10) | 0.0564 (13) | 0.0357 (10) | 0.0200 (9) | 0.0207 (9) | 0.0177 (9) |
C31 | 0.0377 (10) | 0.0284 (10) | 0.0304 (9) | −0.0103 (8) | 0.0222 (8) | −0.0114 (7) |
C39 | 0.0273 (9) | 0.0358 (10) | 0.0250 (9) | 0.0054 (8) | 0.0081 (7) | 0.0105 (8) |
C38 | 0.0228 (9) | 0.0432 (11) | 0.0351 (10) | 0.0097 (8) | 0.0145 (8) | 0.0084 (9) |
C33 | 0.0217 (8) | 0.0334 (10) | 0.0200 (8) | −0.0061 (7) | 0.0105 (7) | 0.0001 (7) |
C34 | 0.0388 (10) | 0.0336 (10) | 0.0256 (9) | 0.0014 (8) | 0.0220 (8) | 0.0028 (8) |
C32 | 0.0411 (11) | 0.0252 (9) | 0.0324 (9) | −0.0104 (8) | 0.0254 (8) | −0.0063 (7) |
O5—C12 | 1.3627 (17) | C18—C17 | 1.392 (2) |
O5—H5O | 0.98 (2) | C18—C21 | 1.5080 (19) |
O6—C13 | 1.3608 (17) | C17—C16 | 1.384 (2) |
O6—H6O | 0.94 (2) | C17—H17 | 0.9500 |
O7—C1 | 1.3611 (17) | C21—C22 | 1.535 (2) |
O7—C9 | 1.3776 (16) | C21—H21A | 0.9900 |
O2—C5 | 1.3595 (16) | C21—H21B | 0.9900 |
O2—H2O | 0.91 (2) | C20—H20 | 0.9500 |
O4—C8 | 1.3469 (17) | C27—C26 | 1.385 (2) |
O4—H4O | 0.95 (2) | C27—H27 | 0.9500 |
O3—C7 | 1.2604 (16) | C22—H22A | 0.9900 |
O1—C3 | 1.3449 (18) | C22—H22B | 0.9900 |
O1—H1O | 0.95 (2) | C16—H16 | 0.9500 |
C6—C1 | 1.3979 (18) | C26—H26 | 0.9500 |
C6—C5 | 1.420 (2) | C24—C25 | 1.383 (2) |
C6—C7 | 1.436 (2) | C24—H24 | 0.9500 |
C1—C2 | 1.386 (2) | C25—H25 | 0.9500 |
C9—C8 | 1.3703 (18) | N3—C32 | 1.333 (2) |
C9—C10 | 1.468 (2) | N3—C28 | 1.341 (2) |
C7—C8 | 1.450 (2) | N4—C37 | 1.330 (2) |
C12—C11 | 1.387 (2) | N4—C38 | 1.330 (2) |
C12—C13 | 1.4100 (19) | C30—C31 | 1.385 (2) |
C10—C15 | 1.4015 (19) | C30—C29 | 1.397 (2) |
C10—C11 | 1.404 (2) | C30—C33 | 1.5170 (19) |
C13—C14 | 1.384 (2) | C29—C28 | 1.383 (2) |
C14—C15 | 1.384 (2) | C29—H29 | 0.9500 |
C14—H14 | 0.9500 | C28—H28 | 0.9500 |
C15—H15 | 0.9500 | C35—C39 | 1.373 (2) |
C11—H11 | 0.9500 | C35—C36 | 1.386 (2) |
C3—C2 | 1.394 (2) | C35—C34 | 1.512 (2) |
C3—C4 | 1.4053 (19) | C37—C36 | 1.386 (2) |
C4—C5 | 1.374 (2) | C37—H37 | 0.9500 |
C4—H4 | 0.9500 | C36—H36 | 0.9500 |
C2—H2 | 0.9500 | C31—C32 | 1.391 (2) |
N1—C16 | 1.336 (2) | C31—H31 | 0.9500 |
N1—C20 | 1.339 (2) | C39—C38 | 1.385 (2) |
N2—C26 | 1.339 (2) | C39—H39 | 0.9500 |
N2—C25 | 1.339 (2) | C38—H38 | 0.9500 |
C19—C20 | 1.387 (2) | C33—C34 | 1.524 (2) |
C19—C18 | 1.391 (2) | C33—H33A | 0.9900 |
C19—H19 | 0.9500 | C33—H33B | 0.9900 |
C23—C24 | 1.392 (2) | C34—H34A | 0.9900 |
C23—C27 | 1.393 (2) | C34—H34B | 0.9900 |
C23—C22 | 1.512 (2) | C32—H32 | 0.9500 |
C12—O5—H5O | 110.0 (11) | H21A—C21—H21B | 107.7 |
C13—O6—H6O | 109.0 (12) | N1—C20—C19 | 123.11 (15) |
C1—O7—C9 | 121.47 (11) | N1—C20—H20 | 118.4 |
C5—O2—H2O | 107.1 (13) | C19—C20—H20 | 118.4 |
C8—O4—H4O | 116.4 (12) | C26—C27—C23 | 119.56 (15) |
C3—O1—H1O | 109.6 (12) | C26—C27—H27 | 120.2 |
C1—C6—C5 | 117.29 (13) | C23—C27—H27 | 120.2 |
C1—C6—C7 | 120.07 (13) | C23—C22—C21 | 111.14 (13) |
C5—C6—C7 | 122.63 (12) | C23—C22—H22A | 109.4 |
O7—C1—C2 | 116.48 (12) | C21—C22—H22A | 109.4 |
O7—C1—C6 | 120.38 (12) | C23—C22—H22B | 109.4 |
C2—C1—C6 | 123.13 (13) | C21—C22—H22B | 109.4 |
C8—C9—O7 | 120.85 (13) | H22A—C22—H22B | 108.0 |
C8—C9—C10 | 129.17 (13) | N1—C16—C17 | 123.87 (14) |
O7—C9—C10 | 109.96 (11) | N1—C16—H16 | 118.1 |
O3—C7—C6 | 122.33 (13) | C17—C16—H16 | 118.1 |
O3—C7—C8 | 120.82 (13) | N2—C26—C27 | 123.47 (15) |
C6—C7—C8 | 116.84 (12) | N2—C26—H26 | 118.3 |
O5—C12—C11 | 123.26 (12) | C27—C26—H26 | 118.3 |
O5—C12—C13 | 117.12 (12) | C25—C24—C23 | 119.62 (15) |
C11—C12—C13 | 119.61 (13) | C25—C24—H24 | 120.2 |
C15—C10—C11 | 118.62 (13) | C23—C24—H24 | 120.2 |
C15—C10—C9 | 118.57 (13) | N2—C25—C24 | 123.53 (15) |
C11—C10—C9 | 122.80 (12) | N2—C25—H25 | 118.2 |
O6—C13—C14 | 122.40 (12) | C24—C25—H25 | 118.2 |
O6—C13—C12 | 118.28 (13) | C32—N3—C28 | 116.75 (13) |
C14—C13—C12 | 119.32 (13) | C37—N4—C38 | 116.50 (13) |
C15—C14—C13 | 121.07 (13) | C31—C30—C29 | 116.72 (13) |
C15—C14—H14 | 119.5 | C31—C30—C33 | 122.96 (14) |
C13—C14—H14 | 119.5 | C29—C30—C33 | 120.32 (14) |
C14—C15—C10 | 120.34 (13) | C28—C29—C30 | 119.21 (14) |
C14—C15—H15 | 119.8 | C28—C29—H29 | 120.4 |
C10—C15—H15 | 119.8 | C30—C29—H29 | 120.4 |
O4—C8—C9 | 120.54 (13) | N3—C28—C29 | 124.00 (14) |
O4—C8—C7 | 119.26 (12) | N3—C28—H28 | 118.0 |
C9—C8—C7 | 120.18 (13) | C29—C28—H28 | 118.0 |
C12—C11—C10 | 121.00 (12) | C39—C35—C36 | 116.34 (14) |
C12—C11—H11 | 119.5 | C39—C35—C34 | 121.06 (15) |
C10—C11—H11 | 119.5 | C36—C35—C34 | 122.60 (15) |
O1—C3—C2 | 121.72 (13) | N4—C37—C36 | 123.14 (16) |
O1—C3—C4 | 117.15 (13) | N4—C37—H37 | 118.4 |
C2—C3—C4 | 121.12 (13) | C36—C37—H37 | 118.4 |
C5—C4—C3 | 119.77 (14) | C37—C36—C35 | 120.22 (16) |
C5—C4—H4 | 120.1 | C37—C36—H36 | 119.9 |
C3—C4—H4 | 120.1 | C35—C36—H36 | 119.9 |
O2—C5—C4 | 120.26 (13) | C30—C31—C32 | 120.22 (15) |
O2—C5—C6 | 118.85 (13) | C30—C31—H31 | 119.9 |
C4—C5—C6 | 120.89 (13) | C32—C31—H31 | 119.9 |
C1—C2—C3 | 117.79 (13) | C35—C39—C38 | 120.02 (15) |
C1—C2—H2 | 121.1 | C35—C39—H39 | 120.0 |
C3—C2—H2 | 121.1 | C38—C39—H39 | 120.0 |
C16—N1—C20 | 116.74 (13) | N4—C38—C39 | 123.75 (15) |
C26—N2—C25 | 116.84 (13) | N4—C38—H38 | 118.1 |
C20—C19—C18 | 120.08 (14) | C39—C38—H38 | 118.1 |
C20—C19—H19 | 120.0 | C30—C33—C34 | 114.96 (13) |
C18—C19—H19 | 120.0 | C30—C33—H33A | 108.5 |
C24—C23—C27 | 116.98 (14) | C34—C33—H33A | 108.5 |
C24—C23—C22 | 121.90 (14) | C30—C33—H33B | 108.5 |
C27—C23—C22 | 121.12 (14) | C34—C33—H33B | 108.5 |
C19—C18—C17 | 116.61 (13) | H33A—C33—H33B | 107.5 |
C19—C18—C21 | 121.80 (14) | C35—C34—C33 | 113.22 (14) |
C17—C18—C21 | 121.56 (14) | C35—C34—H34A | 108.9 |
C16—C17—C18 | 119.54 (15) | C33—C34—H34A | 108.9 |
C16—C17—H17 | 120.2 | C35—C34—H34B | 108.9 |
C18—C17—H17 | 120.2 | C33—C34—H34B | 108.9 |
C18—C21—C22 | 113.65 (13) | H34A—C34—H34B | 107.7 |
C18—C21—H21A | 108.8 | N3—C32—C31 | 123.06 (15) |
C22—C21—H21A | 108.8 | N3—C32—H32 | 118.5 |
C18—C21—H21B | 108.8 | C31—C32—H32 | 118.5 |
C22—C21—H21B | 108.8 |
C27H22N2O7 | Z = 8 |
Mr = 486.46 | F(000) = 2032 |
Monoclinic, P21/c | Dx = 1.414 Mg m−3 |
a = 13.3624 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5540 (4) Å | µ = 0.10 mm−1 |
c = 32.5542 (10) Å | T = 296 K |
β = 95.517 (3)° | Plate, yellow |
V = 4569.7 (3) Å3 | 0.35 × 0.25 × 0.15 mm |
Absorption correction: multi-scan Empirical absorption correction | Rint = 0.050 |
Tmin = 0.808, Tmax = 1.000 | θmax = 27.5°, θmin = 2.5° |
43116 measured reflections | h = −17→17 |
10476 independent reflections | k = −13→13 |
7148 reflections with I > 2σ(I) | l = −42→42 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0612P)2 + 1.213P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
10476 reflections | Δρmax = 0.22 e Å−3 |
689 parameters | Δρmin = −0.28 e Å−3 |
C27H22N2O7 | V = 4569.7 (3) Å3 |
Mr = 486.46 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.3624 (4) Å | µ = 0.10 mm−1 |
b = 10.5540 (4) Å | T = 296 K |
c = 32.5542 (10) Å | 0.35 × 0.25 × 0.15 mm |
β = 95.517 (3)° |
Absorption correction: multi-scan Empirical absorption correction | 10476 independent reflections |
Tmin = 0.808, Tmax = 1.000 | 7148 reflections with I > 2σ(I) |
43116 measured reflections | Rint = 0.050 |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.22 e Å−3 |
10476 reflections | Δρmin = −0.28 e Å−3 |
689 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O14 | 0.14620 (8) | 0.17885 (12) | 0.97818 (3) | 0.0350 (3) | |
O9 | −0.07882 (10) | 0.09360 (15) | 1.08142 (4) | 0.0446 (4) | |
O7 | 0.32587 (9) | 0.15948 (12) | 1.27571 (4) | 0.0359 (3) | |
O10 | 0.11720 (9) | 0.12579 (15) | 1.10012 (4) | 0.0469 (4) | |
O4 | 0.16715 (10) | 0.20252 (15) | 1.18021 (4) | 0.0462 (4) | |
O11 | 0.30290 (9) | 0.13862 (17) | 1.07407 (4) | 0.0502 (4) | |
O8 | −0.20539 (9) | 0.17285 (16) | 0.94450 (4) | 0.0490 (4) | |
O3 | 0.31998 (10) | 0.06635 (15) | 1.15473 (4) | 0.0488 (4) | |
O13 | 0.58056 (11) | 0.13847 (18) | 0.92241 (4) | 0.0582 (5) | |
O12 | 0.59768 (10) | 0.17147 (17) | 1.00508 (4) | 0.0553 (4) | |
O5 | −0.04358 (11) | 0.48832 (17) | 1.24886 (5) | 0.0616 (5) | |
O6 | 0.01369 (13) | 0.55197 (17) | 1.32774 (5) | 0.0650 (5) | |
O2 | 0.48819 (11) | −0.06545 (16) | 1.17195 (4) | 0.0542 (4) | |
O1 | 0.62581 (12) | −0.07255 (18) | 1.30923 (5) | 0.0659 (5) | |
C17 | −0.02732 (12) | 0.18211 (18) | 0.96057 (5) | 0.0347 (4) | |
H17 | −0.0162 | 0.2017 | 0.9335 | 0.042* | |
C9 | 0.24878 (12) | 0.20299 (17) | 1.24830 (5) | 0.0311 (4) | |
C7 | 0.32281 (13) | 0.09165 (18) | 1.19254 (5) | 0.0349 (4) | |
C11 | 0.09785 (14) | 0.34548 (19) | 1.24786 (6) | 0.0394 (4) | |
H11 | 0.0791 | 0.3235 | 1.2205 | 0.047* | |
N1 | 0.17845 (13) | −0.23807 (19) | 1.13127 (5) | 0.0514 (5) | |
C18 | −0.12455 (12) | 0.16505 (18) | 0.97194 (5) | 0.0347 (4) | |
C8 | 0.24409 (12) | 0.16645 (17) | 1.20809 (5) | 0.0330 (4) | |
C16 | 0.05165 (12) | 0.16891 (17) | 0.99073 (5) | 0.0308 (4) | |
C10 | 0.18396 (13) | 0.29079 (17) | 1.26859 (5) | 0.0332 (4) | |
C25 | 0.32220 (12) | 0.16214 (18) | 0.98387 (5) | 0.0339 (4) | |
C23 | 0.22118 (12) | 0.14825 (18) | 1.04634 (5) | 0.0344 (4) | |
C1 | 0.40132 (13) | 0.08514 (18) | 1.26332 (5) | 0.0351 (4) | |
C24 | 0.23044 (12) | 0.16311 (17) | 1.00530 (5) | 0.0317 (4) | |
C6 | 0.40205 (13) | 0.05032 (18) | 1.22206 (5) | 0.0352 (4) | |
C22 | 0.12386 (13) | 0.13945 (18) | 1.06199 (5) | 0.0342 (4) | |
C21 | 0.03845 (12) | 0.14493 (17) | 1.03216 (5) | 0.0306 (4) | |
C5 | 0.48260 (14) | −0.0273 (2) | 1.21122 (6) | 0.0423 (5) | |
C20 | −0.06159 (12) | 0.12518 (18) | 1.04239 (5) | 0.0328 (4) | |
C19 | −0.14127 (13) | 0.13513 (18) | 1.01275 (5) | 0.0356 (4) | |
H19 | −0.2064 | 0.1221 | 1.0197 | 0.043* | |
C27 | 0.50348 (13) | 0.1638 (2) | 0.98555 (6) | 0.0397 (4) | |
C13 | 0.06777 (14) | 0.4647 (2) | 1.30801 (6) | 0.0422 (5) | |
C14 | 0.15161 (15) | 0.4117 (2) | 1.32900 (6) | 0.0452 (5) | |
H14 | 0.1693 | 0.4335 | 1.3564 | 0.054* | |
N2 | 0.38892 (13) | −0.29881 (19) | 1.41224 (5) | 0.0516 (5) | |
C28 | 0.49631 (13) | 0.1472 (2) | 0.94278 (6) | 0.0412 (5) | |
C15 | 0.21006 (14) | 0.32599 (19) | 1.30957 (6) | 0.0404 (4) | |
H15 | 0.2672 | 0.2916 | 1.3240 | 0.049* | |
C30 | 0.31620 (14) | 0.1462 (2) | 0.94110 (6) | 0.0433 (5) | |
H30 | 0.2536 | 0.1402 | 0.9260 | 0.052* | |
C4 | 0.55522 (15) | −0.0654 (2) | 1.24113 (6) | 0.0480 (5) | |
H4 | 0.6077 | −0.1162 | 1.2340 | 0.058* | |
C3 | 0.55180 (15) | −0.0291 (2) | 1.28222 (6) | 0.0470 (5) | |
C47 | 0.27077 (16) | −0.2387 (2) | 1.15010 (6) | 0.0536 (6) | |
H47 | 0.3240 | −0.2213 | 1.1346 | 0.064* | |
C29 | 0.40289 (14) | 0.1393 (2) | 0.92095 (6) | 0.0477 (5) | |
H29 | 0.3979 | 0.1293 | 0.8924 | 0.057* | |
C12 | 0.04063 (14) | 0.4310 (2) | 1.26721 (6) | 0.0411 (4) | |
C2 | 0.47418 (14) | 0.0477 (2) | 1.29376 (6) | 0.0430 (5) | |
H2 | 0.4717 | 0.0727 | 1.3210 | 0.052* | |
N4 | 0.07818 (17) | 0.5361 (2) | 0.83517 (6) | 0.0665 (6) | |
C26 | 0.41709 (13) | 0.1717 (2) | 1.00559 (6) | 0.0388 (4) | |
H26 | 0.4223 | 0.1837 | 1.0340 | 0.047* | |
N3 | 0.35862 (18) | 0.4848 (2) | 1.11064 (6) | 0.0698 (6) | |
C52 | 0.33453 (17) | −0.2592 (2) | 1.32814 (6) | 0.0521 (5) | |
C46 | 0.29180 (16) | −0.2638 (2) | 1.19146 (6) | 0.0556 (6) | |
H46 | 0.3580 | −0.2628 | 1.2033 | 0.067* | |
C48 | 0.23410 (19) | −0.3185 (3) | 1.26096 (6) | 0.0636 (7) | |
H48A | 0.1710 | −0.3138 | 1.2734 | 0.076* | |
H48B | 0.2591 | −0.4045 | 1.2644 | 0.076* | |
C50 | 0.45679 (16) | −0.2790 (3) | 1.38576 (7) | 0.0603 (6) | |
H50 | 0.5243 | −0.2787 | 1.3958 | 0.072* | |
C44 | 0.11914 (17) | −0.2924 (3) | 1.19576 (7) | 0.0603 (6) | |
H44 | 0.0647 | −0.3115 | 1.2104 | 0.072* | |
C31 | 0.0254 (2) | 0.5912 (3) | 0.86294 (8) | 0.0692 (7) | |
H31 | −0.0309 | 0.6381 | 0.8532 | 0.083* | |
C45 | 0.21436 (16) | −0.2906 (2) | 1.21547 (6) | 0.0486 (5) | |
C54 | 0.29401 (16) | −0.3001 (3) | 1.39640 (7) | 0.0611 (7) | |
H54 | 0.2448 | −0.3139 | 1.4143 | 0.073* | |
C33 | 0.1295 (2) | 0.5152 (2) | 0.92053 (8) | 0.0672 (7) | |
C43 | 0.10422 (17) | −0.2658 (3) | 1.15431 (7) | 0.0664 (7) | |
H43 | 0.0388 | −0.2673 | 1.1417 | 0.080* | |
C51 | 0.43282 (17) | −0.2589 (3) | 1.34444 (7) | 0.0620 (6) | |
H51 | 0.4836 | −0.2450 | 1.3274 | 0.074* | |
C53 | 0.26333 (17) | −0.2825 (3) | 1.35549 (7) | 0.0595 (6) | |
H53 | 0.1954 | −0.2862 | 1.3461 | 0.071* | |
C32 | 0.0482 (2) | 0.5833 (3) | 0.90463 (8) | 0.0685 (7) | |
H32 | 0.0081 | 0.6246 | 0.9223 | 0.082* | |
C36 | 0.1549 (2) | 0.5046 (3) | 0.96686 (8) | 0.0781 (8) | |
H36A | 0.1141 | 0.5649 | 0.9803 | 0.094* | |
H36B | 0.1367 | 0.4204 | 0.9756 | 0.094* | |
C34 | 0.1860 (3) | 0.4580 (3) | 0.89227 (9) | 0.0946 (11) | |
H34 | 0.2426 | 0.4108 | 0.9013 | 0.113* | |
C35 | 0.1579 (2) | 0.4713 (3) | 0.85023 (8) | 0.0874 (10) | |
H35 | 0.1972 | 0.4325 | 0.8318 | 0.105* | |
C40 | 0.2923 (2) | 0.5136 (2) | 1.02690 (7) | 0.0642 (7) | |
C41 | 0.3903 (2) | 0.5347 (3) | 1.04174 (8) | 0.0804 (8) | |
H41 | 0.4370 | 0.5587 | 1.0238 | 0.096* | |
C49 | 0.3069 (2) | −0.2315 (3) | 1.28322 (7) | 0.0801 (9) | |
H49A | 0.2796 | −0.1464 | 1.2809 | 0.096* | |
H49B | 0.3681 | −0.2322 | 1.2694 | 0.096* | |
C42 | 0.4196 (2) | 0.5205 (3) | 1.08320 (9) | 0.0831 (9) | |
H42 | 0.4864 | 0.5370 | 1.0924 | 0.100* | |
C37 | 0.2612 (2) | 0.5273 (3) | 0.98101 (8) | 0.0873 (9) | |
H37A | 0.2781 | 0.6124 | 0.9728 | 0.105* | |
H37B | 0.3015 | 0.4691 | 0.9664 | 0.105* | |
C39 | 0.2285 (2) | 0.4783 (3) | 1.05534 (8) | 0.0756 (8) | |
H39 | 0.1610 | 0.4636 | 1.0470 | 0.091* | |
C38 | 0.2645 (2) | 0.4644 (3) | 1.09654 (8) | 0.0739 (8) | |
H38 | 0.2196 | 0.4394 | 1.1151 | 0.089* | |
H2O | 0.4364 (19) | −0.029 (2) | 1.1573 (8) | 0.072 (8)* | |
H9O | −0.018 (2) | 0.095 (2) | 1.0986 (8) | 0.078 (8)* | |
H4O | 0.178 (2) | 0.172 (3) | 1.1570 (9) | 0.081 (9)* | |
H13O | 0.633 (2) | 0.141 (3) | 0.9403 (8) | 0.084 (9)* | |
H11O | 0.286 (2) | 0.113 (3) | 1.0988 (9) | 0.089 (9)* | |
H1O | 0.6212 (19) | −0.048 (3) | 1.3353 (8) | 0.079 (9)* | |
H12O | 0.595 (2) | 0.180 (3) | 1.0344 (9) | 0.088 (9)* | |
H8O | −0.1860 (19) | 0.195 (3) | 0.9189 (8) | 0.082 (9)* | |
H5O | −0.0516 (18) | 0.475 (2) | 1.2199 (8) | 0.075 (8)* | |
H6O | −0.042 (2) | 0.572 (3) | 1.3116 (8) | 0.083 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O14 | 0.0221 (6) | 0.0562 (8) | 0.0265 (6) | −0.0014 (5) | 0.0015 (5) | 0.0055 (6) |
O9 | 0.0300 (7) | 0.0792 (10) | 0.0249 (6) | 0.0006 (7) | 0.0040 (5) | 0.0053 (7) |
O7 | 0.0330 (6) | 0.0459 (7) | 0.0279 (6) | 0.0084 (5) | −0.0015 (5) | −0.0013 (5) |
O10 | 0.0319 (7) | 0.0853 (11) | 0.0231 (6) | 0.0008 (7) | 0.0014 (5) | 0.0016 (7) |
O4 | 0.0338 (7) | 0.0728 (10) | 0.0303 (7) | 0.0139 (7) | −0.0057 (6) | −0.0088 (7) |
O11 | 0.0255 (6) | 0.0981 (12) | 0.0264 (7) | −0.0004 (7) | −0.0011 (5) | 0.0071 (7) |
O8 | 0.0254 (6) | 0.0910 (12) | 0.0293 (7) | 0.0004 (7) | −0.0039 (5) | 0.0092 (7) |
O3 | 0.0448 (8) | 0.0736 (10) | 0.0273 (7) | 0.0146 (7) | 0.0001 (6) | −0.0030 (7) |
O13 | 0.0293 (7) | 0.1128 (14) | 0.0338 (8) | 0.0048 (8) | 0.0089 (6) | 0.0005 (8) |
O12 | 0.0253 (7) | 0.1080 (13) | 0.0324 (8) | −0.0046 (7) | 0.0011 (6) | 0.0000 (8) |
O5 | 0.0509 (9) | 0.0864 (12) | 0.0450 (9) | 0.0337 (8) | −0.0085 (7) | −0.0107 (8) |
O6 | 0.0599 (10) | 0.0886 (13) | 0.0454 (9) | 0.0368 (9) | −0.0005 (8) | −0.0163 (8) |
O2 | 0.0480 (9) | 0.0815 (11) | 0.0332 (8) | 0.0207 (8) | 0.0040 (6) | −0.0086 (7) |
O1 | 0.0591 (10) | 0.0890 (13) | 0.0453 (9) | 0.0373 (9) | −0.0165 (8) | −0.0074 (9) |
C17 | 0.0277 (9) | 0.0511 (11) | 0.0249 (9) | 0.0014 (8) | 0.0007 (7) | 0.0049 (8) |
C9 | 0.0249 (8) | 0.0369 (9) | 0.0308 (9) | −0.0017 (7) | −0.0007 (7) | 0.0022 (7) |
C7 | 0.0329 (9) | 0.0442 (10) | 0.0276 (9) | −0.0008 (8) | 0.0022 (7) | 0.0008 (8) |
C11 | 0.0353 (10) | 0.0512 (12) | 0.0309 (9) | 0.0048 (8) | −0.0005 (8) | −0.0040 (8) |
N1 | 0.0481 (10) | 0.0740 (13) | 0.0312 (9) | 0.0027 (9) | 0.0002 (8) | 0.0046 (8) |
C18 | 0.0262 (8) | 0.0483 (11) | 0.0287 (9) | 0.0029 (8) | −0.0013 (7) | 0.0002 (8) |
C8 | 0.0260 (8) | 0.0417 (10) | 0.0305 (9) | −0.0001 (7) | −0.0009 (7) | −0.0002 (8) |
C16 | 0.0236 (8) | 0.0391 (10) | 0.0298 (9) | −0.0005 (7) | 0.0037 (7) | −0.0002 (7) |
C10 | 0.0292 (9) | 0.0387 (10) | 0.0320 (9) | −0.0004 (7) | 0.0036 (7) | 0.0010 (8) |
C25 | 0.0265 (8) | 0.0470 (11) | 0.0282 (9) | −0.0015 (7) | 0.0019 (7) | 0.0019 (8) |
C23 | 0.0241 (8) | 0.0505 (11) | 0.0276 (9) | 0.0013 (7) | −0.0015 (7) | −0.0005 (8) |
C1 | 0.0332 (9) | 0.0394 (10) | 0.0323 (9) | 0.0039 (8) | 0.0020 (7) | −0.0007 (8) |
C24 | 0.0234 (8) | 0.0435 (10) | 0.0273 (9) | −0.0012 (7) | −0.0014 (7) | −0.0004 (7) |
C6 | 0.0309 (9) | 0.0439 (10) | 0.0301 (9) | 0.0027 (8) | −0.0001 (7) | 0.0001 (8) |
C22 | 0.0277 (9) | 0.0488 (11) | 0.0257 (8) | 0.0011 (8) | 0.0015 (7) | −0.0007 (8) |
C21 | 0.0240 (8) | 0.0416 (10) | 0.0260 (8) | 0.0014 (7) | 0.0011 (6) | −0.0008 (7) |
C5 | 0.0371 (10) | 0.0535 (12) | 0.0361 (10) | 0.0067 (9) | 0.0029 (8) | −0.0027 (9) |
C20 | 0.0287 (8) | 0.0461 (10) | 0.0239 (8) | 0.0019 (7) | 0.0040 (7) | −0.0015 (7) |
C19 | 0.0236 (8) | 0.0529 (11) | 0.0306 (9) | 0.0022 (8) | 0.0035 (7) | −0.0003 (8) |
C27 | 0.0277 (9) | 0.0605 (13) | 0.0307 (9) | −0.0022 (8) | 0.0010 (7) | 0.0019 (9) |
C13 | 0.0398 (10) | 0.0526 (12) | 0.0345 (10) | 0.0109 (9) | 0.0052 (8) | −0.0033 (9) |
C14 | 0.0467 (11) | 0.0597 (13) | 0.0284 (9) | 0.0110 (10) | −0.0006 (8) | −0.0062 (9) |
N2 | 0.0417 (9) | 0.0793 (13) | 0.0330 (9) | −0.0028 (9) | −0.0008 (7) | 0.0073 (9) |
C28 | 0.0298 (9) | 0.0638 (13) | 0.0306 (9) | 0.0012 (9) | 0.0056 (7) | 0.0020 (9) |
C15 | 0.0386 (10) | 0.0496 (11) | 0.0322 (10) | 0.0075 (8) | −0.0016 (8) | 0.0015 (8) |
C30 | 0.0285 (9) | 0.0728 (14) | 0.0278 (9) | 0.0002 (9) | −0.0018 (7) | −0.0016 (9) |
C4 | 0.0403 (11) | 0.0595 (13) | 0.0432 (11) | 0.0184 (10) | −0.0010 (9) | −0.0038 (10) |
C3 | 0.0409 (11) | 0.0576 (13) | 0.0402 (11) | 0.0126 (10) | −0.0074 (9) | −0.0014 (10) |
C47 | 0.0466 (12) | 0.0793 (16) | 0.0351 (11) | −0.0058 (11) | 0.0044 (9) | 0.0046 (11) |
C29 | 0.0333 (10) | 0.0845 (16) | 0.0253 (9) | 0.0021 (10) | 0.0028 (8) | −0.0038 (10) |
C12 | 0.0337 (9) | 0.0530 (12) | 0.0357 (10) | 0.0087 (8) | −0.0017 (8) | −0.0002 (9) |
C2 | 0.0424 (11) | 0.0546 (12) | 0.0304 (9) | 0.0115 (9) | −0.0046 (8) | −0.0030 (9) |
N4 | 0.0790 (14) | 0.0710 (14) | 0.0457 (11) | 0.0205 (11) | −0.0138 (10) | −0.0094 (10) |
C26 | 0.0285 (9) | 0.0612 (13) | 0.0264 (9) | −0.0031 (8) | 0.0021 (7) | −0.0002 (8) |
N3 | 0.0822 (16) | 0.0757 (15) | 0.0478 (12) | −0.0102 (12) | −0.0127 (11) | 0.0034 (11) |
C52 | 0.0579 (13) | 0.0670 (15) | 0.0307 (10) | −0.0126 (11) | 0.0005 (9) | 0.0034 (10) |
C46 | 0.0409 (11) | 0.0872 (18) | 0.0375 (11) | −0.0050 (11) | −0.0021 (9) | 0.0104 (11) |
C48 | 0.0649 (15) | 0.0894 (19) | 0.0350 (11) | −0.0202 (13) | −0.0019 (11) | 0.0107 (12) |
C50 | 0.0371 (11) | 0.0968 (19) | 0.0463 (13) | 0.0023 (12) | 0.0009 (9) | 0.0122 (12) |
C44 | 0.0436 (12) | 0.099 (2) | 0.0385 (12) | −0.0040 (12) | 0.0060 (9) | 0.0065 (12) |
C31 | 0.0730 (17) | 0.0780 (18) | 0.0544 (15) | 0.0192 (14) | −0.0054 (13) | −0.0018 (13) |
C45 | 0.0520 (12) | 0.0615 (14) | 0.0317 (10) | −0.0052 (10) | 0.0008 (9) | 0.0044 (10) |
C54 | 0.0430 (12) | 0.106 (2) | 0.0345 (11) | −0.0113 (12) | 0.0041 (9) | 0.0088 (12) |
C33 | 0.097 (2) | 0.0508 (14) | 0.0489 (14) | 0.0034 (14) | −0.0188 (13) | −0.0054 (11) |
C43 | 0.0438 (12) | 0.114 (2) | 0.0399 (12) | 0.0041 (13) | −0.0022 (10) | 0.0085 (13) |
C51 | 0.0506 (13) | 0.0943 (19) | 0.0427 (12) | −0.0002 (12) | 0.0128 (10) | 0.0098 (12) |
C53 | 0.0420 (12) | 0.0957 (19) | 0.0393 (12) | −0.0127 (12) | −0.0042 (9) | 0.0115 (12) |
C32 | 0.0843 (18) | 0.0707 (17) | 0.0493 (14) | 0.0082 (14) | −0.0003 (13) | −0.0031 (13) |
C36 | 0.107 (2) | 0.0688 (18) | 0.0533 (15) | −0.0057 (16) | −0.0182 (15) | 0.0032 (13) |
C34 | 0.123 (3) | 0.086 (2) | 0.0656 (18) | 0.055 (2) | −0.0356 (18) | −0.0151 (16) |
C35 | 0.108 (2) | 0.091 (2) | 0.0580 (16) | 0.0473 (19) | −0.0197 (16) | −0.0237 (15) |
C40 | 0.0839 (18) | 0.0566 (15) | 0.0488 (14) | −0.0034 (13) | −0.0115 (13) | 0.0024 (11) |
C41 | 0.084 (2) | 0.096 (2) | 0.0584 (17) | −0.0108 (17) | −0.0039 (15) | 0.0109 (15) |
C49 | 0.099 (2) | 0.105 (2) | 0.0338 (12) | −0.0401 (18) | −0.0064 (13) | 0.0108 (13) |
C42 | 0.0790 (19) | 0.104 (2) | 0.0615 (17) | −0.0180 (17) | −0.0167 (15) | 0.0099 (16) |
C37 | 0.099 (2) | 0.106 (2) | 0.0528 (16) | −0.0126 (19) | −0.0160 (15) | 0.0125 (16) |
C39 | 0.0745 (18) | 0.090 (2) | 0.0582 (16) | −0.0109 (15) | −0.0159 (14) | 0.0030 (15) |
C38 | 0.0786 (18) | 0.092 (2) | 0.0483 (14) | −0.0124 (16) | −0.0085 (13) | 0.0012 (14) |
O14—C16 | 1.3688 (19) | N2—C50 | 1.327 (3) |
O14—C24 | 1.3722 (19) | C28—C29 | 1.378 (3) |
O9—C20 | 1.355 (2) | C15—H15 | 0.9300 |
O9—H9O | 0.94 (3) | C30—C29 | 1.387 (2) |
O7—C1 | 1.369 (2) | C30—H30 | 0.9300 |
O7—C9 | 1.375 (2) | C4—C3 | 1.396 (3) |
O10—C22 | 1.261 (2) | C4—H4 | 0.9300 |
O4—C8 | 1.359 (2) | C3—C2 | 1.396 (3) |
O4—H4O | 0.85 (3) | C47—C46 | 1.375 (3) |
O11—C23 | 1.352 (2) | C47—H47 | 0.9300 |
O11—H11O | 0.90 (3) | C29—H29 | 0.9300 |
O8—C18 | 1.336 (2) | C2—H2 | 0.9300 |
O8—H8O | 0.93 (3) | N4—C35 | 1.320 (3) |
O3—C7 | 1.256 (2) | N4—C31 | 1.332 (3) |
O13—C28 | 1.363 (2) | C26—H26 | 0.9300 |
O13—H13O | 0.87 (3) | N3—C38 | 1.315 (3) |
O12—C27 | 1.357 (2) | N3—C42 | 1.321 (4) |
O12—H12O | 0.96 (3) | C52—C51 | 1.368 (3) |
O5—C12 | 1.364 (2) | C52—C53 | 1.386 (3) |
O5—H5O | 0.95 (3) | C52—C49 | 1.502 (3) |
O6—C13 | 1.369 (2) | C46—C45 | 1.385 (3) |
O6—H6O | 0.90 (3) | C46—H46 | 0.9300 |
O2—C5 | 1.349 (2) | C48—C49 | 1.477 (3) |
O2—H2O | 0.89 (3) | C48—C45 | 1.508 (3) |
O1—C3 | 1.340 (2) | C48—H48A | 0.9700 |
O1—H1O | 0.90 (3) | C48—H48B | 0.9700 |
C17—C16 | 1.378 (2) | C50—C51 | 1.369 (3) |
C17—C18 | 1.396 (2) | C50—H50 | 0.9300 |
C17—H17 | 0.9300 | C44—C45 | 1.369 (3) |
C9—C8 | 1.360 (2) | C44—C43 | 1.374 (3) |
C9—C10 | 1.468 (2) | C44—H44 | 0.9300 |
C7—C6 | 1.428 (2) | C31—C32 | 1.365 (3) |
C7—C8 | 1.445 (2) | C31—H31 | 0.9300 |
C11—C12 | 1.374 (3) | C54—C53 | 1.368 (3) |
C11—C10 | 1.401 (2) | C54—H54 | 0.9300 |
C11—H11 | 0.9300 | C33—C32 | 1.363 (4) |
N1—C47 | 1.324 (3) | C33—C34 | 1.384 (4) |
N1—C43 | 1.332 (3) | C33—C36 | 1.518 (3) |
C18—C19 | 1.404 (2) | C43—H43 | 0.9300 |
C16—C21 | 1.400 (2) | C51—H51 | 0.9300 |
C10—C15 | 1.396 (2) | C53—H53 | 0.9300 |
C25—C26 | 1.395 (2) | C32—H32 | 0.9300 |
C25—C30 | 1.397 (2) | C36—C37 | 1.470 (4) |
C25—C24 | 1.468 (2) | C36—H36A | 0.9700 |
C23—C24 | 1.363 (2) | C36—H36B | 0.9700 |
C23—C22 | 1.445 (2) | C34—C35 | 1.391 (4) |
C1—C2 | 1.378 (2) | C34—H34 | 0.9300 |
C1—C6 | 1.394 (2) | C35—H35 | 0.9300 |
C6—C5 | 1.424 (3) | C40—C39 | 1.368 (4) |
C22—C21 | 1.427 (2) | C40—C41 | 1.370 (4) |
C21—C20 | 1.424 (2) | C40—C37 | 1.519 (3) |
C5—C4 | 1.367 (3) | C41—C42 | 1.377 (4) |
C20—C19 | 1.370 (2) | C41—H41 | 0.9300 |
C19—H19 | 0.9300 | C49—H49A | 0.9700 |
C27—C26 | 1.382 (2) | C49—H49B | 0.9700 |
C27—C28 | 1.398 (3) | C42—H42 | 0.9300 |
C13—C14 | 1.374 (3) | C37—H37A | 0.9700 |
C13—C12 | 1.389 (3) | C37—H37B | 0.9700 |
C14—C15 | 1.387 (3) | C39—C38 | 1.388 (3) |
C14—H14 | 0.9300 | C39—H39 | 0.9300 |
N2—C54 | 1.322 (3) | C38—H38 | 0.9300 |
C16—O14—C24 | 121.49 (13) | C28—C29—C30 | 120.61 (17) |
C20—O9—H9O | 109.8 (16) | C28—C29—H29 | 119.7 |
C1—O7—C9 | 121.81 (13) | C30—C29—H29 | 119.7 |
C8—O4—H4O | 107.5 (18) | O5—C12—C11 | 124.24 (17) |
C23—O11—H11O | 111.0 (18) | O5—C12—C13 | 115.70 (17) |
C18—O8—H8O | 109.8 (16) | C11—C12—C13 | 120.06 (17) |
C28—O13—H13O | 108.9 (18) | C1—C2—C3 | 117.69 (17) |
C27—O12—H12O | 110.5 (16) | C1—C2—H2 | 121.2 |
C12—O5—H5O | 112.3 (15) | C3—C2—H2 | 121.2 |
C13—O6—H6O | 109.3 (18) | C35—N4—C31 | 115.8 (2) |
C5—O2—H2O | 105.6 (17) | C27—C26—C25 | 121.07 (16) |
C3—O1—H1O | 114.1 (17) | C27—C26—H26 | 119.5 |
C16—C17—C18 | 117.81 (16) | C25—C26—H26 | 119.5 |
C16—C17—H17 | 121.1 | C38—N3—C42 | 116.3 (2) |
C18—C17—H17 | 121.1 | C51—C52—C53 | 116.33 (19) |
C8—C9—O7 | 119.48 (15) | C51—C52—C49 | 120.9 (2) |
C8—C9—C10 | 129.60 (16) | C53—C52—C49 | 122.7 (2) |
O7—C9—C10 | 110.86 (14) | C47—C46—C45 | 119.9 (2) |
O3—C7—C6 | 123.01 (16) | C47—C46—H46 | 120.0 |
O3—C7—C8 | 120.32 (16) | C45—C46—H46 | 120.0 |
C6—C7—C8 | 116.67 (15) | C49—C48—C45 | 113.9 (2) |
C12—C11—C10 | 121.14 (17) | C49—C48—H48A | 108.8 |
C12—C11—H11 | 119.4 | C45—C48—H48A | 108.8 |
C10—C11—H11 | 119.4 | C49—C48—H48B | 108.8 |
C47—N1—C43 | 116.70 (18) | C45—C48—H48B | 108.8 |
O8—C18—C17 | 121.86 (16) | H48A—C48—H48B | 107.7 |
O8—C18—C19 | 117.02 (15) | N2—C50—C51 | 123.6 (2) |
C17—C18—C19 | 121.10 (16) | N2—C50—H50 | 118.2 |
O4—C8—C9 | 121.69 (16) | C51—C50—H50 | 118.2 |
O4—C8—C7 | 116.65 (15) | C45—C44—C43 | 119.9 (2) |
C9—C8—C7 | 121.61 (15) | C45—C44—H44 | 120.1 |
O14—C16—C17 | 116.44 (15) | C43—C44—H44 | 120.1 |
O14—C16—C21 | 120.45 (15) | N4—C31—C32 | 124.5 (2) |
C17—C16—C21 | 123.10 (15) | N4—C31—H31 | 117.8 |
C15—C10—C11 | 117.95 (17) | C32—C31—H31 | 117.8 |
C15—C10—C9 | 119.60 (16) | C44—C45—C46 | 116.71 (19) |
C11—C10—C9 | 122.41 (16) | C44—C45—C48 | 121.6 (2) |
C26—C25—C30 | 118.44 (16) | C46—C45—C48 | 121.64 (19) |
C26—C25—C24 | 121.24 (15) | N2—C54—C53 | 124.4 (2) |
C30—C25—C24 | 120.27 (15) | N2—C54—H54 | 117.8 |
O11—C23—C24 | 121.31 (15) | C53—C54—H54 | 117.8 |
O11—C23—C22 | 117.16 (15) | C32—C33—C34 | 116.3 (2) |
C24—C23—C22 | 121.52 (15) | C32—C33—C36 | 120.7 (3) |
O7—C1—C2 | 116.23 (16) | C34—C33—C36 | 123.0 (3) |
O7—C1—C6 | 120.59 (15) | N1—C43—C44 | 123.5 (2) |
C2—C1—C6 | 123.18 (17) | N1—C43—H43 | 118.2 |
C23—C24—O14 | 119.91 (14) | C44—C43—H43 | 118.2 |
C23—C24—C25 | 128.60 (15) | C50—C51—C52 | 120.4 (2) |
O14—C24—C25 | 111.47 (14) | C50—C51—H51 | 119.8 |
C1—C6—C5 | 117.78 (16) | C52—C51—H51 | 119.8 |
C1—C6—C7 | 119.65 (16) | C54—C53—C52 | 119.3 (2) |
C5—C6—C7 | 122.57 (16) | C54—C53—H53 | 120.3 |
O10—C22—C21 | 123.16 (15) | C52—C53—H53 | 120.3 |
O10—C22—C23 | 120.37 (15) | C31—C32—C33 | 120.2 (3) |
C21—C22—C23 | 116.47 (15) | C31—C32—H32 | 119.9 |
C16—C21—C20 | 117.37 (15) | C33—C32—H32 | 119.9 |
C16—C21—C22 | 119.76 (15) | C37—C36—C33 | 114.6 (3) |
C20—C21—C22 | 122.86 (15) | C37—C36—H36A | 108.6 |
O2—C5—C4 | 119.12 (17) | C33—C36—H36A | 108.6 |
O2—C5—C6 | 121.25 (17) | C37—C36—H36B | 108.6 |
C4—C5—C6 | 119.63 (18) | C33—C36—H36B | 108.6 |
O9—C20—C19 | 119.25 (15) | H36A—C36—H36B | 107.6 |
O9—C20—C21 | 120.23 (15) | C33—C34—C35 | 119.8 (3) |
C19—C20—C21 | 120.51 (15) | C33—C34—H34 | 120.1 |
C20—C19—C18 | 119.98 (15) | C35—C34—H34 | 120.1 |
C20—C19—H19 | 120.0 | N4—C35—C34 | 123.3 (3) |
C18—C19—H19 | 120.0 | N4—C35—H35 | 118.3 |
O12—C27—C26 | 123.68 (16) | C34—C35—H35 | 118.3 |
O12—C27—C28 | 116.48 (16) | C39—C40—C41 | 116.2 (2) |
C26—C27—C28 | 119.84 (16) | C39—C40—C37 | 124.2 (3) |
O6—C13—C14 | 118.84 (18) | C41—C40—C37 | 119.5 (3) |
O6—C13—C12 | 121.34 (17) | C40—C41—C42 | 120.0 (3) |
C14—C13—C12 | 119.80 (17) | C40—C41—H41 | 120.0 |
C13—C14—C15 | 120.42 (18) | C42—C41—H41 | 120.0 |
C13—C14—H14 | 119.8 | C48—C49—C52 | 116.5 (2) |
C15—C14—H14 | 119.8 | C48—C49—H49A | 108.2 |
C54—N2—C50 | 115.99 (18) | C52—C49—H49A | 108.2 |
O13—C28—C29 | 119.63 (17) | C48—C49—H49B | 108.2 |
O13—C28—C27 | 120.82 (16) | C52—C49—H49B | 108.2 |
C29—C28—C27 | 119.55 (16) | H49A—C49—H49B | 107.3 |
C14—C15—C10 | 120.63 (17) | N3—C42—C41 | 123.9 (3) |
C14—C15—H15 | 119.7 | N3—C42—H42 | 118.1 |
C10—C15—H15 | 119.7 | C41—C42—H42 | 118.1 |
C29—C30—C25 | 120.48 (17) | C36—C37—C40 | 117.2 (3) |
C29—C30—H30 | 119.8 | C36—C37—H37A | 108.0 |
C25—C30—H30 | 119.8 | C40—C37—H37A | 108.0 |
C5—C4—C3 | 121.02 (18) | C36—C37—H37B | 108.0 |
C5—C4—H4 | 119.5 | C40—C37—H37B | 108.0 |
C3—C4—H4 | 119.5 | H37A—C37—H37B | 107.2 |
O1—C3—C2 | 122.86 (18) | C40—C39—C38 | 120.2 (3) |
O1—C3—C4 | 116.45 (18) | C40—C39—H39 | 119.9 |
C2—C3—C4 | 120.69 (17) | C38—C39—H39 | 119.9 |
N1—C47—C46 | 123.2 (2) | N3—C38—C39 | 123.4 (3) |
N1—C47—H47 | 118.4 | N3—C38—H38 | 118.3 |
C46—C47—H47 | 118.4 | C39—C38—H38 | 118.3 |
C29H26N4O8 | V = 1327.8 (4) Å3 |
Mr = 558.54 | Z = 2 |
Triclinic, P1 | F(000) = 584 |
a = 10.0918 (17) Å | Dx = 1.397 Mg m−3 |
b = 11.4244 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 13.052 (2) Å | µ = 0.10 mm−1 |
α = 98.573 (7)° | T = 150 K |
β = 95.190 (7)° | Plate, red |
γ = 115.078 (8)° | 0.30 × 0.20 × 0.12 mm |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | Rint = 0.074 |
Tmin = 0.613, Tmax = 1.000 | θmax = 26.0°, θmin = 3.2° |
11363 measured reflections | h = −12→12 |
5197 independent reflections | k = −14→14 |
3551 reflections with I > 2σ(I) | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.265 | w = 1/[σ2(Fo2) + (0.0982P)2 + 2.1601P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
5197 reflections | Δρmax = 1.80 e Å−3 |
390 parameters | Δρmin = −0.36 e Å−3 |
C29H26N4O8 | γ = 115.078 (8)° |
Mr = 558.54 | V = 1327.8 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.0918 (17) Å | Mo Kα radiation |
b = 11.4244 (19) Å | µ = 0.10 mm−1 |
c = 13.052 (2) Å | T = 150 K |
α = 98.573 (7)° | 0.30 × 0.20 × 0.12 mm |
β = 95.190 (7)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 5197 independent reflections |
Tmin = 0.613, Tmax = 1.000 | 3551 reflections with I > 2σ(I) |
11363 measured reflections | Rint = 0.074 |
R[F2 > 2σ(F2)] = 0.090 | 0 restraints |
wR(F2) = 0.265 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Δρmax = 1.80 e Å−3 |
5197 reflections | Δρmin = −0.36 e Å−3 |
390 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.5397 (3) | 0.1620 (3) | −0.4290 (2) | 0.0258 (7) | |
O5 | 0.6675 (4) | 0.1563 (3) | 0.3936 (2) | 0.0267 (7) | |
O2 | 0.8870 (4) | 0.0205 (3) | −0.3052 (2) | 0.0283 (7) | |
O7 | 0.6165 (3) | 0.1533 (3) | −0.06765 (19) | 0.0191 (6) | |
O3 | 0.9167 (3) | 0.0085 (3) | −0.1047 (2) | 0.0242 (6) | |
O6 | 0.4766 (4) | 0.2678 (3) | 0.3825 (2) | 0.0263 (7) | |
O4 | 0.8522 (3) | 0.0562 (3) | 0.0892 (2) | 0.0242 (7) | |
C3 | 0.6082 (5) | 0.1397 (4) | −0.3460 (3) | 0.0211 (8) | |
N1 | 1.2815 (4) | 0.3701 (4) | 0.3479 (3) | 0.0285 (8) | |
N2 | 0.9685 (4) | 0.5212 (4) | 0.3207 (3) | 0.0318 (9) | |
C7 | 0.8236 (4) | 0.0545 (4) | −0.0954 (3) | 0.0188 (8) | |
C14 | 0.4775 (4) | 0.2558 (4) | 0.1955 (3) | 0.0211 (8) | |
H14 | 0.4111 | 0.2945 | 0.1900 | 0.025* | |
N3 | 0.9862 (4) | 0.6115 (4) | 0.3948 (3) | 0.0302 (8) | |
C15 | 0.5289 (4) | 0.2198 (4) | 0.1071 (3) | 0.0193 (8) | |
H15 | 0.4961 | 0.2330 | 0.0411 | 0.023* | |
C2 | 0.5760 (4) | 0.1607 (4) | −0.2457 (3) | 0.0201 (8) | |
H2A | 0.5057 | 0.1935 | −0.2324 | 0.024* | |
C11 | 0.6728 (4) | 0.1427 (4) | 0.2118 (3) | 0.0186 (8) | |
H11 | 0.7384 | 0.1032 | 0.2175 | 0.022* | |
C10 | 0.6287 (4) | 0.1643 (4) | 0.1134 (3) | 0.0185 (8) | |
N4 | 0.6617 (4) | 0.7497 (4) | 0.3880 (3) | 0.0310 (9) | |
C12 | 0.6211 (4) | 0.1788 (4) | 0.3002 (3) | 0.0196 (8) | |
C9 | 0.6820 (4) | 0.1297 (4) | 0.0178 (3) | 0.0168 (8) | |
C6 | 0.7547 (4) | 0.0850 (4) | −0.1812 (3) | 0.0185 (8) | |
C8 | 0.7841 (4) | 0.0815 (4) | 0.0061 (3) | 0.0181 (8) | |
C4 | 0.7143 (5) | 0.0932 (4) | −0.3656 (3) | 0.0217 (8) | |
H4 | 0.7362 | 0.0809 | −0.4345 | 0.026* | |
C22 | 0.8987 (5) | 0.7684 (5) | 0.4581 (4) | 0.0297 (10) | |
H22 | 0.9880 | 0.8138 | 0.5081 | 0.036* | |
C13 | 0.5228 (4) | 0.2355 (4) | 0.2926 (3) | 0.0196 (8) | |
C17 | 1.2036 (5) | 0.5346 (5) | 0.4127 (3) | 0.0291 (10) | |
H17 | 1.2205 | 0.6109 | 0.4629 | 0.035* | |
C21 | 0.7900 (6) | 0.8119 (5) | 0.4563 (3) | 0.0330 (10) | |
H21 | 0.8069 | 0.8890 | 0.5056 | 0.040* | |
C20 | 1.1608 (5) | 0.3143 (4) | 0.2727 (4) | 0.0299 (10) | |
H20 | 1.1450 | 0.2367 | 0.2245 | 0.036* | |
C25 | 0.6400 (6) | 0.6421 (5) | 0.3185 (4) | 0.0336 (10) | |
H25 | 0.5496 | 0.5980 | 0.2696 | 0.040* | |
C19 | 1.0586 (5) | 0.3635 (4) | 0.2618 (4) | 0.0313 (10) | |
H19 | 0.9754 | 0.3226 | 0.2064 | 0.038* | |
C16 | 1.3017 (5) | 0.4794 (5) | 0.4156 (3) | 0.0296 (10) | |
H16 | 1.3880 | 0.5209 | 0.4684 | 0.036* | |
C24 | 0.7426 (5) | 0.5919 (5) | 0.3142 (4) | 0.0314 (10) | |
H24 | 0.7233 | 0.5149 | 0.2639 | 0.038* | |
C1 | 0.6504 (4) | 0.1321 (4) | −0.1654 (3) | 0.0177 (8) | |
O8 | 0.6735 (6) | 0.5940 (4) | −0.0674 (4) | 0.0710 (14) | |
C23 | 0.8740 (5) | 0.6571 (4) | 0.3853 (3) | 0.0274 (9) | |
C18 | 1.0805 (5) | 0.4749 (4) | 0.3343 (3) | 0.0280 (9) | |
C5 | 0.7853 (4) | 0.0660 (4) | −0.2856 (3) | 0.0202 (8) | |
C27 | 0.6744 (9) | 0.4737 (6) | −0.0691 (8) | 0.093 (3) | |
H27A | 0.6816 | 0.4365 | −0.1407 | 0.111* | |
H27B | 0.5806 | 0.4116 | −0.0507 | 0.111* | |
C30 | 0.8878 (7) | 0.6378 (6) | 0.0450 (5) | 0.0572 (16) | |
H30A | 0.9263 | 0.6606 | 0.1214 | 0.069* | |
H30B | 0.9720 | 0.6751 | 0.0071 | 0.069* | |
C26 | 0.8009 (8) | 0.4896 (6) | 0.0063 (7) | 0.071 (2) | |
H26A | 0.8621 | 0.4525 | −0.0284 | 0.085* | |
H26B | 0.7668 | 0.4453 | 0.0651 | 0.085* | |
C29 | 0.7742 (8) | 0.6870 (6) | 0.0208 (6) | 0.0637 (17) | |
H29A | 0.7227 | 0.6916 | 0.0812 | 0.076* | |
H29B | 0.8217 | 0.7760 | 0.0042 | 0.076* | |
H1O | 0.475 (7) | 0.197 (6) | −0.415 (5) | 0.052 (17)* | |
H5O | 0.607 (7) | 0.163 (6) | 0.436 (5) | 0.046 (16)* | |
H2O | 0.918 (8) | 0.009 (7) | −0.249 (6) | 0.07 (2)* | |
H6O | 0.409 (7) | 0.300 (6) | 0.367 (5) | 0.056 (18)* | |
H4O | 0.931 (7) | 0.033 (6) | 0.075 (5) | 0.053 (17)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0356 (17) | 0.0411 (18) | 0.0135 (13) | 0.0275 (15) | 0.0053 (12) | 0.0093 (12) |
O5 | 0.0348 (17) | 0.0435 (19) | 0.0126 (13) | 0.0254 (15) | 0.0067 (12) | 0.0104 (12) |
O2 | 0.0350 (17) | 0.0476 (19) | 0.0173 (15) | 0.0314 (16) | 0.0063 (13) | 0.0087 (13) |
O7 | 0.0248 (14) | 0.0267 (15) | 0.0096 (12) | 0.0146 (12) | 0.0034 (10) | 0.0050 (11) |
O3 | 0.0288 (15) | 0.0357 (17) | 0.0166 (13) | 0.0231 (13) | 0.0025 (12) | 0.0038 (12) |
O6 | 0.0360 (17) | 0.0386 (18) | 0.0150 (13) | 0.0256 (15) | 0.0080 (12) | 0.0058 (12) |
O4 | 0.0305 (16) | 0.0386 (17) | 0.0132 (13) | 0.0241 (14) | 0.0038 (12) | 0.0066 (12) |
C3 | 0.026 (2) | 0.024 (2) | 0.0163 (18) | 0.0133 (17) | 0.0035 (16) | 0.0061 (15) |
N1 | 0.033 (2) | 0.035 (2) | 0.0259 (18) | 0.0213 (17) | 0.0111 (16) | 0.0078 (16) |
N2 | 0.029 (2) | 0.033 (2) | 0.036 (2) | 0.0181 (17) | 0.0034 (16) | 0.0008 (17) |
C7 | 0.0191 (19) | 0.0197 (19) | 0.0171 (18) | 0.0088 (15) | 0.0019 (15) | 0.0018 (15) |
C14 | 0.023 (2) | 0.027 (2) | 0.0170 (18) | 0.0142 (17) | 0.0040 (16) | 0.0053 (16) |
N3 | 0.028 (2) | 0.030 (2) | 0.034 (2) | 0.0162 (16) | 0.0054 (16) | 0.0028 (16) |
C15 | 0.025 (2) | 0.025 (2) | 0.0099 (17) | 0.0129 (17) | 0.0020 (15) | 0.0044 (15) |
C2 | 0.026 (2) | 0.026 (2) | 0.0163 (18) | 0.0172 (17) | 0.0063 (16) | 0.0059 (16) |
C11 | 0.0204 (19) | 0.023 (2) | 0.0158 (18) | 0.0129 (16) | 0.0038 (15) | 0.0049 (15) |
C10 | 0.0208 (19) | 0.0183 (19) | 0.0155 (18) | 0.0078 (15) | 0.0027 (15) | 0.0036 (15) |
N4 | 0.038 (2) | 0.045 (2) | 0.0247 (18) | 0.0303 (19) | 0.0100 (16) | 0.0115 (17) |
C12 | 0.024 (2) | 0.024 (2) | 0.0124 (17) | 0.0109 (16) | 0.0013 (15) | 0.0060 (15) |
C9 | 0.0179 (18) | 0.0181 (18) | 0.0130 (17) | 0.0076 (15) | 0.0007 (14) | 0.0021 (14) |
C6 | 0.022 (2) | 0.0185 (19) | 0.0154 (18) | 0.0100 (16) | 0.0023 (15) | 0.0028 (15) |
C8 | 0.0217 (19) | 0.0211 (19) | 0.0136 (17) | 0.0117 (16) | 0.0011 (15) | 0.0039 (15) |
C4 | 0.028 (2) | 0.029 (2) | 0.0130 (17) | 0.0168 (18) | 0.0065 (16) | 0.0049 (16) |
C22 | 0.030 (2) | 0.033 (2) | 0.029 (2) | 0.018 (2) | 0.0060 (19) | 0.0045 (19) |
C13 | 0.025 (2) | 0.022 (2) | 0.0118 (17) | 0.0111 (16) | 0.0047 (15) | 0.0013 (15) |
C17 | 0.032 (2) | 0.031 (2) | 0.027 (2) | 0.0179 (19) | 0.0074 (19) | 0.0033 (18) |
C21 | 0.048 (3) | 0.038 (3) | 0.024 (2) | 0.029 (2) | 0.009 (2) | 0.0073 (19) |
C20 | 0.033 (2) | 0.025 (2) | 0.032 (2) | 0.0148 (19) | 0.0075 (19) | 0.0010 (18) |
C25 | 0.037 (3) | 0.045 (3) | 0.026 (2) | 0.025 (2) | 0.0033 (19) | 0.009 (2) |
C19 | 0.027 (2) | 0.031 (2) | 0.034 (2) | 0.0134 (19) | 0.0048 (19) | −0.0011 (19) |
C16 | 0.029 (2) | 0.038 (3) | 0.025 (2) | 0.018 (2) | 0.0069 (18) | 0.0045 (19) |
C24 | 0.033 (2) | 0.033 (2) | 0.031 (2) | 0.019 (2) | 0.0059 (19) | 0.0028 (19) |
C1 | 0.0205 (19) | 0.0200 (19) | 0.0131 (17) | 0.0093 (16) | 0.0041 (15) | 0.0031 (15) |
O8 | 0.079 (3) | 0.052 (3) | 0.075 (3) | 0.028 (2) | −0.022 (3) | 0.018 (2) |
C23 | 0.028 (2) | 0.033 (2) | 0.028 (2) | 0.0185 (19) | 0.0080 (18) | 0.0090 (18) |
C18 | 0.027 (2) | 0.030 (2) | 0.032 (2) | 0.0163 (19) | 0.0104 (19) | 0.0089 (19) |
C5 | 0.023 (2) | 0.025 (2) | 0.0171 (19) | 0.0138 (17) | 0.0064 (16) | 0.0052 (16) |
C27 | 0.081 (5) | 0.032 (3) | 0.134 (7) | 0.012 (3) | −0.044 (5) | 0.008 (4) |
C30 | 0.045 (3) | 0.045 (3) | 0.062 (4) | 0.004 (3) | −0.004 (3) | 0.015 (3) |
C26 | 0.050 (4) | 0.041 (3) | 0.111 (6) | 0.011 (3) | −0.007 (4) | 0.028 (4) |
C29 | 0.070 (4) | 0.047 (4) | 0.071 (4) | 0.029 (3) | 0.000 (4) | 0.001 (3) |
O1—C3 | 1.347 (5) | C12—C13 | 1.400 (6) |
O1—H1O | 0.92 (7) | C9—C8 | 1.369 (5) |
O5—C12 | 1.365 (4) | C6—C1 | 1.389 (5) |
O5—H5O | 0.89 (6) | C6—C5 | 1.429 (5) |
O2—C5 | 1.360 (5) | C4—C5 | 1.360 (6) |
O2—H2O | 0.82 (7) | C4—H4 | 0.9500 |
O7—C1 | 1.364 (4) | C22—C21 | 1.382 (6) |
O7—C9 | 1.364 (4) | C22—C23 | 1.382 (6) |
O3—C7 | 1.263 (5) | C22—H22 | 0.9500 |
O6—C13 | 1.359 (5) | C17—C18 | 1.378 (7) |
O6—H6O | 0.92 (7) | C17—C16 | 1.381 (6) |
O4—C8 | 1.364 (5) | C17—H17 | 0.9500 |
O4—H4O | 0.96 (6) | C21—H21 | 0.9500 |
C3—C2 | 1.388 (5) | C20—C19 | 1.375 (6) |
C3—C4 | 1.408 (6) | C20—H20 | 0.9500 |
N1—C20 | 1.339 (6) | C25—C24 | 1.381 (6) |
N1—C16 | 1.343 (6) | C25—H25 | 0.9500 |
N2—N3 | 1.243 (5) | C19—C18 | 1.389 (6) |
N2—C18 | 1.445 (6) | C19—H19 | 0.9500 |
C7—C6 | 1.429 (5) | C16—H16 | 0.9500 |
C7—C8 | 1.444 (5) | C24—C23 | 1.382 (7) |
C14—C15 | 1.385 (5) | C24—H24 | 0.9500 |
C14—C13 | 1.393 (5) | O8—C27 | 1.375 (8) |
C14—H14 | 0.9500 | O8—C29 | 1.412 (8) |
N3—C23 | 1.437 (6) | C27—C26 | 1.468 (10) |
C15—C10 | 1.402 (5) | C27—H27A | 0.9900 |
C15—H15 | 0.9500 | C27—H27B | 0.9900 |
C2—C1 | 1.391 (5) | C30—C29 | 1.505 (9) |
C2—H2A | 0.9500 | C30—C26 | 1.516 (9) |
C11—C12 | 1.387 (5) | C30—H30A | 0.9900 |
C11—C10 | 1.411 (5) | C30—H30B | 0.9900 |
C11—H11 | 0.9500 | C26—H26A | 0.9900 |
C10—C9 | 1.468 (5) | C26—H26B | 0.9900 |
N4—C25 | 1.337 (6) | C29—H29A | 0.9900 |
N4—C21 | 1.342 (6) | C29—H29B | 0.9900 |
C3—O1—H1O | 117 (4) | N4—C21—C22 | 122.8 (4) |
C12—O5—H5O | 106 (4) | N4—C21—H21 | 118.6 |
C5—O2—H2O | 107 (5) | C22—C21—H21 | 118.6 |
C1—O7—C9 | 122.3 (3) | N1—C20—C19 | 123.3 (4) |
C13—O6—H6O | 109 (4) | N1—C20—H20 | 118.3 |
C8—O4—H4O | 115 (4) | C19—C20—H20 | 118.3 |
O1—C3—C2 | 121.9 (4) | N4—C25—C24 | 123.2 (5) |
O1—C3—C4 | 116.9 (3) | N4—C25—H25 | 118.4 |
C2—C3—C4 | 121.2 (4) | C24—C25—H25 | 118.4 |
C20—N1—C16 | 117.5 (4) | C20—C19—C18 | 118.0 (4) |
N3—N2—C18 | 112.2 (4) | C20—C19—H19 | 121.0 |
O3—C7—C6 | 123.2 (3) | C18—C19—H19 | 121.0 |
O3—C7—C8 | 120.2 (3) | N1—C16—C17 | 123.6 (4) |
C6—C7—C8 | 116.6 (3) | N1—C16—H16 | 118.2 |
C15—C14—C13 | 120.3 (4) | C17—C16—H16 | 118.2 |
C15—C14—H14 | 119.8 | C25—C24—C23 | 118.0 (4) |
C13—C14—H14 | 119.8 | C25—C24—H24 | 121.0 |
N2—N3—C23 | 113.6 (4) | C23—C24—H24 | 121.0 |
C14—C15—C10 | 121.0 (3) | O7—C1—C6 | 120.4 (3) |
C14—C15—H15 | 119.5 | O7—C1—C2 | 116.6 (3) |
C10—C15—H15 | 119.5 | C6—C1—C2 | 123.1 (3) |
C3—C2—C1 | 117.7 (4) | C27—O8—C29 | 109.5 (5) |
C3—C2—H2A | 121.2 | C24—C23—C22 | 119.9 (4) |
C1—C2—H2A | 121.2 | C24—C23—N3 | 124.1 (4) |
C12—C11—C10 | 120.5 (3) | C22—C23—N3 | 115.9 (4) |
C12—C11—H11 | 119.7 | C17—C18—C19 | 120.0 (4) |
C10—C11—H11 | 119.7 | C17—C18—N2 | 124.1 (4) |
C15—C10—C11 | 118.3 (3) | C19—C18—N2 | 115.8 (4) |
C15—C10—C9 | 119.0 (3) | O2—C5—C4 | 119.5 (3) |
C11—C10—C9 | 122.6 (3) | O2—C5—C6 | 119.6 (3) |
C25—N4—C21 | 118.0 (4) | C4—C5—C6 | 120.9 (4) |
O5—C12—C11 | 118.3 (3) | O8—C27—C26 | 109.9 (6) |
O5—C12—C13 | 121.4 (3) | O8—C27—H27A | 109.7 |
C11—C12—C13 | 120.3 (3) | C26—C27—H27A | 109.7 |
O7—C9—C8 | 119.6 (3) | O8—C27—H27B | 109.7 |
O7—C9—C10 | 111.1 (3) | C26—C27—H27B | 109.7 |
C8—C9—C10 | 129.3 (3) | H27A—C27—H27B | 108.2 |
C1—C6—C7 | 119.9 (3) | C29—C30—C26 | 103.1 (5) |
C1—C6—C5 | 117.3 (3) | C29—C30—H30A | 111.1 |
C7—C6—C5 | 122.8 (3) | C26—C30—H30A | 111.1 |
O4—C8—C9 | 121.6 (3) | C29—C30—H30B | 111.1 |
O4—C8—C7 | 117.2 (3) | C26—C30—H30B | 111.1 |
C9—C8—C7 | 121.2 (3) | H30A—C30—H30B | 109.1 |
C5—C4—C3 | 119.8 (3) | C27—C26—C30 | 104.1 (5) |
C5—C4—H4 | 120.1 | C27—C26—H26A | 110.9 |
C3—C4—H4 | 120.1 | C30—C26—H26A | 110.9 |
C21—C22—C23 | 118.2 (4) | C27—C26—H26B | 110.9 |
C21—C22—H22 | 120.9 | C30—C26—H26B | 110.9 |
C23—C22—H22 | 120.9 | H26A—C26—H26B | 109.0 |
O6—C13—C14 | 123.6 (4) | O8—C29—C30 | 105.1 (5) |
O6—C13—C12 | 116.9 (3) | O8—C29—H29A | 110.7 |
C14—C13—C12 | 119.5 (3) | C30—C29—H29A | 110.7 |
C18—C17—C16 | 117.6 (4) | O8—C29—H29B | 110.7 |
C18—C17—H17 | 121.2 | C30—C29—H29B | 110.7 |
C16—C17—H17 | 121.2 | H29A—C29—H29B | 108.8 |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O8i | 0.95 | 2.49 | 3.267 (6) | 139 |
C11—H11···O4 | 0.95 | 2.24 | 2.895 (5) | 126 |
C4—H4···O5ii | 0.95 | 2.66 | 3.365 (5) | 132 |
C21—H21···O2iii | 0.95 | 2.55 | 3.404 (6) | 149 |
C16—H16···O6iv | 0.95 | 2.61 | 3.388 (6) | 140 |
O1—H1O···N4i | 0.92 (7) | 1.77 (7) | 2.684 (5) | 175 (6) |
O5—H5O···O1v | 0.89 (6) | 1.94 (6) | 2.757 (4) | 153 (5) |
O5—H5O···O6 | 0.89 (6) | 2.25 (6) | 2.727 (4) | 114 (5) |
O2—H2O···O3 | 0.82 (7) | 1.89 (7) | 2.638 (4) | 152 (7) |
O6—H6O···N1vi | 0.92 (7) | 1.80 (7) | 2.719 (5) | 175 (6) |
O4—H4O···O3vii | 0.96 (6) | 1.82 (6) | 2.728 (4) | 157 (5) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y, z−1; (iii) x, y+1, z+1; (iv) −x+2, −y+1, −z+1; (v) x, y, z+1; (vi) x−1, y, z; (vii) −x+2, −y, −z. |
C25H18N4O7 | Z = 8 |
Mr = 486.43 | F(000) = 2016 |
Monoclinic, C2/c | Dx = 1.508 Mg m−3 |
a = 21.647 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.8623 (16) Å | µ = 0.11 mm−1 |
c = 15.712 (2) Å | T = 150 K |
β = 101.543 (7)° | Plate, red |
V = 4286.2 (10) Å3 | 0.35 × 0.20 × 0.15 mm |
Absorption correction: analytical Bruker, AXS, 2008 | Rint = 0.051 |
Tmin = 0.973, Tmax = 0.983 | θmax = 26.0°, θmin = 1.9° |
24298 measured reflections | h = −25→26 |
4173 independent reflections | k = −15→13 |
3253 reflections with I > 2σ(I) | l = −18→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0625P)2 + 17.9666P] where P = (Fo2 + 2Fc2)/3 |
S = 0.89 | (Δ/σ)max < 0.001 |
4173 reflections | Δρmax = 0.29 e Å−3 |
345 parameters | Δρmin = −0.30 e Å−3 |
C25H18N4O7 | V = 4286.2 (10) Å3 |
Mr = 486.43 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.647 (3) Å | µ = 0.11 mm−1 |
b = 12.8623 (16) Å | T = 150 K |
c = 15.712 (2) Å | 0.35 × 0.20 × 0.15 mm |
β = 101.543 (7)° |
Absorption correction: analytical Bruker, AXS, 2008 | 4173 independent reflections |
Tmin = 0.973, Tmax = 0.983 | 3253 reflections with I > 2σ(I) |
24298 measured reflections | Rint = 0.051 |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.89 | w = 1/[σ2(Fo2) + (0.0625P)2 + 17.9666P] where P = (Fo2 + 2Fc2)/3 |
4173 reflections | Δρmax = 0.29 e Å−3 |
345 parameters | Δρmin = −0.30 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
H1O | 0.1751 (17) | 0.477 (3) | 0.369 (2) | 0.051 (10)* | |
H4O | 0.0968 (16) | 0.276 (3) | −0.149 (2) | 0.046 (10)* | |
H2O | 0.2322 (15) | 0.314 (2) | 0.067 (2) | 0.039 (9)* | |
H5O | −0.1895 (18) | 0.236 (3) | −0.290 (2) | 0.052 (10)* | |
H6O | −0.268 (2) | 0.361 (3) | −0.180 (3) | 0.076 (13)* | |
O7 | 0.01858 (7) | 0.38411 (12) | 0.05880 (10) | 0.0156 (4) | |
O4 | 0.06003 (8) | 0.27776 (14) | −0.13585 (11) | 0.0209 (4) | |
O2 | 0.24283 (7) | 0.33673 (13) | 0.12433 (11) | 0.0179 (4) | |
O1 | 0.13425 (8) | 0.47363 (14) | 0.33498 (11) | 0.0214 (4) | |
O6 | −0.24052 (7) | 0.32590 (14) | −0.20351 (11) | 0.0206 (4) | |
O3 | 0.17450 (7) | 0.29198 (13) | −0.02877 (11) | 0.0181 (4) | |
C6 | 0.13077 (10) | 0.35873 (17) | 0.08704 (15) | 0.0134 (5) | |
O5 | −0.14886 (8) | 0.24076 (14) | −0.27217 (11) | 0.0197 (4) | |
N3 | 0.44827 (9) | 0.49810 (16) | 0.39750 (13) | 0.0204 (5) | |
N4 | 0.25897 (9) | 0.48344 (15) | 0.42547 (13) | 0.0177 (4) | |
C9 | 0.01249 (10) | 0.34562 (17) | −0.02420 (15) | 0.0139 (5) | |
C8 | 0.06466 (10) | 0.31572 (17) | −0.05429 (15) | 0.0149 (5) | |
C7 | 0.12700 (10) | 0.32076 (17) | 0.00013 (15) | 0.0141 (5) | |
N1 | 0.65404 (9) | 0.60021 (17) | 0.34087 (14) | 0.0212 (5) | |
C25 | 0.34263 (11) | 0.58336 (18) | 0.38662 (16) | 0.0198 (5) | |
H25 | 0.3565 | 0.6469 | 0.3659 | 0.024* | |
C11 | −0.07136 (10) | 0.29512 (18) | −0.15211 (15) | 0.0151 (5) | |
H11 | −0.0399 | 0.2665 | −0.1795 | 0.018* | |
C15 | −0.10125 (10) | 0.38352 (17) | −0.03136 (15) | 0.0155 (5) | |
H15 | −0.0905 | 0.4144 | 0.0246 | 0.019* | |
C10 | −0.05378 (10) | 0.34159 (17) | −0.07009 (15) | 0.0141 (5) | |
N2 | 0.46562 (9) | 0.58327 (16) | 0.37248 (14) | 0.0221 (5) | |
C1 | 0.07593 (10) | 0.39105 (17) | 0.11402 (15) | 0.0144 (5) | |
C4 | 0.19075 (10) | 0.40518 (17) | 0.22973 (15) | 0.0150 (5) | |
H4 | 0.2299 | 0.4096 | 0.2697 | 0.018* | |
C18 | 0.53019 (11) | 0.58250 (19) | 0.36147 (15) | 0.0185 (5) | |
C22 | 0.36163 (11) | 0.40782 (18) | 0.43728 (15) | 0.0186 (5) | |
H22 | 0.3888 | 0.3498 | 0.4523 | 0.022* | |
C14 | −0.16419 (10) | 0.38019 (17) | −0.07450 (15) | 0.0161 (5) | |
H14 | −0.1959 | 0.4096 | −0.0479 | 0.019* | |
C5 | 0.18836 (10) | 0.36763 (17) | 0.14777 (15) | 0.0151 (5) | |
C13 | −0.18101 (10) | 0.33449 (17) | −0.15575 (15) | 0.0143 (5) | |
C24 | 0.28143 (11) | 0.57150 (18) | 0.39765 (16) | 0.0188 (5) | |
H24 | 0.2536 | 0.6290 | 0.3848 | 0.023* | |
C21 | 0.38359 (11) | 0.49928 (19) | 0.40674 (15) | 0.0174 (5) | |
C2 | 0.07702 (11) | 0.43065 (18) | 0.19613 (15) | 0.0168 (5) | |
H2 | 0.0393 | 0.4530 | 0.2126 | 0.020* | |
C12 | −0.13385 (10) | 0.29052 (17) | −0.19343 (15) | 0.0146 (5) | |
C23 | 0.29931 (11) | 0.40366 (19) | 0.44510 (16) | 0.0188 (5) | |
H23 | 0.2841 | 0.3410 | 0.4655 | 0.023* | |
C20 | 0.61809 (11) | 0.6843 (2) | 0.34353 (17) | 0.0231 (6) | |
H20 | 0.6362 | 0.7508 | 0.3385 | 0.028* | |
C17 | 0.56628 (11) | 0.49412 (19) | 0.35803 (16) | 0.0211 (5) | |
H17 | 0.5493 | 0.4268 | 0.3629 | 0.025* | |
C19 | 0.55617 (11) | 0.67972 (19) | 0.35317 (17) | 0.0220 (5) | |
H19 | 0.5321 | 0.7413 | 0.3541 | 0.026* | |
C3 | 0.13478 (11) | 0.43709 (17) | 0.25420 (15) | 0.0158 (5) | |
C16 | 0.62773 (11) | 0.5066 (2) | 0.34730 (16) | 0.0218 (5) | |
H16 | 0.6525 | 0.4462 | 0.3443 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O7 | 0.0083 (7) | 0.0238 (8) | 0.0143 (8) | −0.0006 (6) | 0.0011 (6) | −0.0030 (7) |
O4 | 0.0098 (8) | 0.0353 (10) | 0.0182 (9) | −0.0010 (7) | 0.0045 (7) | −0.0060 (7) |
O2 | 0.0094 (7) | 0.0272 (9) | 0.0167 (9) | 0.0040 (7) | 0.0013 (7) | −0.0032 (7) |
O1 | 0.0140 (8) | 0.0341 (10) | 0.0159 (9) | −0.0010 (7) | 0.0023 (7) | −0.0056 (7) |
O6 | 0.0091 (8) | 0.0293 (9) | 0.0224 (10) | 0.0018 (7) | 0.0009 (7) | −0.0043 (7) |
O3 | 0.0099 (8) | 0.0259 (9) | 0.0190 (9) | 0.0009 (7) | 0.0038 (7) | −0.0022 (7) |
C6 | 0.0113 (10) | 0.0143 (10) | 0.0142 (12) | −0.0005 (8) | 0.0016 (9) | 0.0017 (9) |
O5 | 0.0088 (8) | 0.0318 (10) | 0.0179 (9) | −0.0033 (7) | 0.0008 (7) | −0.0058 (7) |
N3 | 0.0151 (10) | 0.0224 (10) | 0.0239 (12) | 0.0000 (8) | 0.0046 (9) | 0.0002 (9) |
N4 | 0.0142 (9) | 0.0224 (10) | 0.0169 (11) | −0.0007 (8) | 0.0038 (8) | −0.0021 (8) |
C9 | 0.0117 (10) | 0.0152 (11) | 0.0144 (12) | −0.0022 (9) | 0.0017 (9) | −0.0012 (9) |
C8 | 0.0126 (10) | 0.0183 (11) | 0.0136 (12) | −0.0022 (9) | 0.0019 (9) | −0.0019 (9) |
C7 | 0.0123 (10) | 0.0154 (11) | 0.0148 (12) | −0.0025 (9) | 0.0035 (9) | 0.0002 (9) |
N1 | 0.0135 (9) | 0.0300 (11) | 0.0197 (11) | −0.0009 (9) | 0.0022 (8) | 0.0012 (9) |
C25 | 0.0195 (12) | 0.0191 (12) | 0.0222 (13) | −0.0006 (10) | 0.0078 (10) | 0.0003 (10) |
C11 | 0.0096 (10) | 0.0197 (11) | 0.0170 (12) | −0.0009 (9) | 0.0047 (9) | 0.0009 (9) |
C15 | 0.0128 (10) | 0.0169 (11) | 0.0162 (12) | −0.0004 (9) | 0.0017 (9) | 0.0011 (9) |
C10 | 0.0120 (11) | 0.0157 (11) | 0.0137 (12) | −0.0001 (9) | 0.0004 (9) | 0.0025 (9) |
N2 | 0.0168 (10) | 0.0261 (11) | 0.0243 (12) | 0.0003 (9) | 0.0064 (9) | 0.0026 (9) |
C1 | 0.0105 (10) | 0.0143 (11) | 0.0178 (12) | −0.0013 (9) | 0.0013 (9) | 0.0010 (9) |
C4 | 0.0109 (10) | 0.0175 (11) | 0.0156 (12) | −0.0012 (9) | 0.0002 (9) | −0.0002 (9) |
C18 | 0.0138 (11) | 0.0257 (13) | 0.0157 (12) | −0.0010 (10) | 0.0022 (9) | 0.0010 (10) |
C22 | 0.0171 (11) | 0.0204 (12) | 0.0175 (13) | 0.0009 (9) | 0.0014 (10) | −0.0009 (9) |
C14 | 0.0113 (10) | 0.0178 (11) | 0.0198 (13) | 0.0009 (9) | 0.0044 (9) | −0.0002 (9) |
C5 | 0.0101 (10) | 0.0166 (11) | 0.0187 (12) | 0.0017 (9) | 0.0030 (9) | 0.0026 (9) |
C13 | 0.0077 (10) | 0.0165 (11) | 0.0176 (12) | −0.0020 (9) | −0.0002 (9) | 0.0045 (9) |
C24 | 0.0176 (11) | 0.0187 (11) | 0.0197 (13) | 0.0025 (9) | 0.0030 (10) | −0.0007 (9) |
C21 | 0.0144 (11) | 0.0239 (12) | 0.0134 (12) | −0.0017 (9) | 0.0012 (9) | −0.0049 (9) |
C2 | 0.0118 (10) | 0.0212 (12) | 0.0176 (13) | −0.0001 (9) | 0.0034 (9) | −0.0011 (9) |
C12 | 0.0128 (11) | 0.0176 (11) | 0.0129 (12) | −0.0016 (9) | 0.0015 (9) | 0.0007 (9) |
C23 | 0.0192 (12) | 0.0203 (12) | 0.0171 (13) | −0.0002 (10) | 0.0043 (10) | 0.0005 (9) |
C20 | 0.0178 (12) | 0.0228 (12) | 0.0291 (15) | −0.0024 (10) | 0.0055 (11) | 0.0048 (11) |
C17 | 0.0181 (12) | 0.0212 (12) | 0.0232 (14) | −0.0024 (10) | 0.0026 (10) | −0.0014 (10) |
C19 | 0.0188 (12) | 0.0216 (12) | 0.0264 (14) | 0.0030 (10) | 0.0063 (11) | 0.0034 (10) |
C3 | 0.0166 (11) | 0.0172 (11) | 0.0139 (12) | −0.0015 (9) | 0.0039 (9) | −0.0002 (9) |
C16 | 0.0180 (12) | 0.0237 (12) | 0.0236 (14) | 0.0012 (10) | 0.0037 (10) | −0.0039 (10) |
O7—C1 | 1.368 (3) | C11—C10 | 1.402 (3) |
O7—C9 | 1.376 (3) | C11—H11 | 0.9500 |
O4—C8 | 1.356 (3) | C15—C14 | 1.396 (3) |
O4—H4O | 0.86 (3) | C15—C10 | 1.403 (3) |
O2—C5 | 1.363 (3) | C15—H15 | 0.9500 |
O2—H2O | 0.92 (3) | N2—C18 | 1.442 (3) |
O1—C3 | 1.356 (3) | C1—C2 | 1.383 (3) |
O1—H1O | 0.94 (4) | C4—C5 | 1.366 (3) |
O6—C13 | 1.359 (3) | C4—C3 | 1.404 (3) |
O6—H6O | 0.89 (4) | C4—H4 | 0.9500 |
O3—C7 | 1.260 (3) | C18—C17 | 1.386 (3) |
C6—C1 | 1.401 (3) | C18—C19 | 1.388 (3) |
C6—C5 | 1.415 (3) | C22—C23 | 1.380 (3) |
C6—C7 | 1.437 (3) | C22—C21 | 1.390 (3) |
O5—C12 | 1.373 (3) | C22—H22 | 0.9500 |
O5—H5O | 0.87 (4) | C14—C13 | 1.386 (3) |
N3—N2 | 1.247 (3) | C14—H14 | 0.9500 |
N3—C21 | 1.436 (3) | C13—C12 | 1.398 (3) |
N4—C24 | 1.340 (3) | C24—H24 | 0.9500 |
N4—C23 | 1.343 (3) | C2—C3 | 1.395 (3) |
C9—C8 | 1.364 (3) | C2—H2 | 0.9500 |
C9—C10 | 1.472 (3) | C23—H23 | 0.9500 |
C8—C7 | 1.447 (3) | C20—C19 | 1.380 (3) |
N1—C20 | 1.338 (3) | C20—H20 | 0.9500 |
N1—C16 | 1.345 (3) | C17—C16 | 1.383 (3) |
C25—C24 | 1.379 (3) | C17—H17 | 0.9500 |
C25—C21 | 1.394 (3) | C19—H19 | 0.9500 |
C25—H25 | 0.9500 | C16—H16 | 0.9500 |
C11—C12 | 1.380 (3) | ||
C1—O7—C9 | 121.82 (17) | C23—C22—C21 | 118.1 (2) |
C8—O4—H4O | 110 (2) | C23—C22—H22 | 120.9 |
C5—O2—H2O | 107 (2) | C21—C22—H22 | 120.9 |
C3—O1—H1O | 112 (2) | C13—C14—C15 | 120.7 (2) |
C13—O6—H6O | 112 (3) | C13—C14—H14 | 119.6 |
C1—C6—C5 | 117.2 (2) | C15—C14—H14 | 119.6 |
C1—C6—C7 | 119.9 (2) | O2—C5—C4 | 119.1 (2) |
C5—C6—C7 | 122.9 (2) | O2—C5—C6 | 119.2 (2) |
C12—O5—H5O | 111 (2) | C4—C5—C6 | 121.8 (2) |
N2—N3—C21 | 112.6 (2) | O6—C13—C14 | 126.0 (2) |
C24—N4—C23 | 117.3 (2) | O6—C13—C12 | 115.2 (2) |
C8—C9—O7 | 120.0 (2) | C14—C13—C12 | 118.8 (2) |
C8—C9—C10 | 127.9 (2) | N4—C24—C25 | 123.7 (2) |
O7—C9—C10 | 112.09 (18) | N4—C24—H24 | 118.1 |
O4—C8—C9 | 121.3 (2) | C25—C24—H24 | 118.1 |
O4—C8—C7 | 117.27 (19) | C22—C21—C25 | 119.3 (2) |
C9—C8—C7 | 121.4 (2) | C22—C21—N3 | 115.7 (2) |
O3—C7—C6 | 123.2 (2) | C25—C21—N3 | 125.0 (2) |
O3—C7—C8 | 120.4 (2) | C1—C2—C3 | 118.5 (2) |
C6—C7—C8 | 116.46 (19) | C1—C2—H2 | 120.7 |
C20—N1—C16 | 117.6 (2) | C3—C2—H2 | 120.7 |
C24—C25—C21 | 118.0 (2) | O5—C12—C11 | 118.5 (2) |
C24—C25—H25 | 121.0 | O5—C12—C13 | 120.6 (2) |
C21—C25—H25 | 121.0 | C11—C12—C13 | 120.9 (2) |
C12—C11—C10 | 120.7 (2) | N4—C23—C22 | 123.5 (2) |
C12—C11—H11 | 119.6 | N4—C23—H23 | 118.2 |
C10—C11—H11 | 119.6 | C22—C23—H23 | 118.2 |
C14—C15—C10 | 120.4 (2) | N1—C20—C19 | 123.5 (2) |
C14—C15—H15 | 119.8 | N1—C20—H20 | 118.2 |
C10—C15—H15 | 119.8 | C19—C20—H20 | 118.2 |
C11—C10—C15 | 118.3 (2) | C16—C17—C18 | 118.2 (2) |
C11—C10—C9 | 121.6 (2) | C16—C17—H17 | 120.9 |
C15—C10—C9 | 120.1 (2) | C18—C17—H17 | 120.9 |
N3—N2—C18 | 113.1 (2) | C20—C19—C18 | 118.0 (2) |
O7—C1—C2 | 117.36 (19) | C20—C19—H19 | 121.0 |
O7—C1—C6 | 120.3 (2) | C18—C19—H19 | 121.0 |
C2—C1—C6 | 122.3 (2) | O1—C3—C2 | 117.3 (2) |
C5—C4—C3 | 119.3 (2) | O1—C3—C4 | 121.8 (2) |
C5—C4—H4 | 120.4 | C2—C3—C4 | 120.9 (2) |
C3—C4—H4 | 120.4 | N1—C16—C17 | 123.0 (2) |
C17—C18—C19 | 119.5 (2) | N1—C16—H16 | 118.5 |
C17—C18—N2 | 125.3 (2) | C17—C16—H16 | 118.5 |
C19—C18—N2 | 115.2 (2) |
C31H26N2O9 | V = 1308.0 (4) Å3 |
Mr = 570.54 | Z = 2 |
Triclinic, P1 | F(000) = 596 |
a = 8.1859 (13) Å | Dx = 1.449 Mg m−3 |
b = 12.787 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 13.173 (2) Å | µ = 0.11 mm−1 |
α = 83.634 (6)° | T = 150 K |
β = 83.848 (6)° | Plate, red |
γ = 73.246 (5)° | 0.45 × 0.25 × 0.12 mm |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | Rint = 0.032 |
Tmin = 0.872, Tmax = 1.000 | θmax = 26.0°, θmin = 3.1° |
12319 measured reflections | h = −10→10 |
5126 independent reflections | k = −15→15 |
4074 reflections with I > 2σ(I) | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.144 | w = 1/[σ2(Fo2) + (0.0626P)2 + 1.188P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
5126 reflections | Δρmax = 1.38 e Å−3 |
396 parameters | Δρmin = −0.43 e Å−3 |
C31H26N2O9 | γ = 73.246 (5)° |
Mr = 570.54 | V = 1308.0 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1859 (13) Å | Mo Kα radiation |
b = 12.787 (2) Å | µ = 0.11 mm−1 |
c = 13.173 (2) Å | T = 150 K |
α = 83.634 (6)° | 0.45 × 0.25 × 0.12 mm |
β = 83.848 (6)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 5126 independent reflections |
Tmin = 0.872, Tmax = 1.000 | 4074 reflections with I > 2σ(I) |
12319 measured reflections | Rint = 0.032 |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 1.38 e Å−3 |
5126 reflections | Δρmin = −0.43 e Å−3 |
396 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.1159 (3) | 0.09134 (17) | 0.66636 (16) | 0.0138 (4) | |
C2 | 0.0192 (3) | 0.14853 (17) | 0.74653 (17) | 0.0154 (5) | |
H2 | −0.0834 | 0.2050 | 0.7351 | 0.018* | |
C3 | 0.0777 (3) | 0.12027 (18) | 0.84393 (17) | 0.0168 (5) | |
C4 | 0.2307 (3) | 0.03916 (18) | 0.86186 (17) | 0.0175 (5) | |
H4 | 0.2699 | 0.0230 | 0.9287 | 0.021* | |
C5 | 0.3238 (3) | −0.01694 (17) | 0.78119 (17) | 0.0162 (5) | |
C6 | 0.2658 (3) | 0.00694 (17) | 0.68123 (16) | 0.0139 (4) | |
C7 | 0.3539 (3) | −0.05370 (17) | 0.59661 (17) | 0.0148 (5) | |
C8 | 0.2823 (3) | −0.01904 (18) | 0.49872 (17) | 0.0150 (5) | |
C9 | 0.1424 (3) | 0.06840 (17) | 0.48702 (16) | 0.0136 (4) | |
C10 | 0.0612 (3) | 0.12044 (17) | 0.39276 (17) | 0.0140 (4) | |
C11 | 0.1227 (3) | 0.08064 (17) | 0.29645 (17) | 0.0139 (4) | |
H11 | 0.2189 | 0.0180 | 0.2916 | 0.017* | |
C12 | 0.0447 (3) | 0.13155 (17) | 0.20850 (16) | 0.0137 (4) | |
C13 | −0.0949 (3) | 0.22525 (17) | 0.21401 (17) | 0.0149 (5) | |
C14 | −0.1573 (3) | 0.26505 (18) | 0.30904 (17) | 0.0156 (5) | |
H14 | −0.2528 | 0.3281 | 0.3134 | 0.019* | |
C15 | −0.0814 (3) | 0.21361 (17) | 0.39726 (17) | 0.0147 (5) | |
H15 | −0.1260 | 0.2415 | 0.4615 | 0.018* | |
C28 | 0.5279 (4) | −0.3897 (2) | 0.3643 (2) | 0.0351 (7) | |
H28A | 0.4258 | −0.3626 | 0.4118 | 0.042* | |
H28B | 0.4926 | −0.4216 | 0.3080 | 0.042* | |
C29 | 0.5972 (4) | −0.2955 (2) | 0.32077 (19) | 0.0301 (6) | |
H29A | 0.6966 | −0.3219 | 0.2711 | 0.036* | |
H29B | 0.5082 | −0.2392 | 0.2840 | 0.036* | |
C30 | 0.7702 (3) | −0.3292 (2) | 0.4584 (2) | 0.0288 (6) | |
H30A | 0.7977 | −0.2960 | 0.5164 | 0.035* | |
H30B | 0.8769 | −0.3556 | 0.4143 | 0.035* | |
C31 | 0.7018 (4) | −0.4248 (2) | 0.4990 (2) | 0.0396 (7) | |
H31A | 0.7906 | −0.4812 | 0.5359 | 0.047* | |
H31B | 0.6012 | −0.3997 | 0.5481 | 0.047* | |
O1 | −0.0089 (2) | 0.17055 (14) | 0.92735 (12) | 0.0219 (4) | |
O2 | 0.4728 (2) | −0.09497 (13) | 0.79698 (13) | 0.0217 (4) | |
O3 | 0.48778 (19) | −0.13271 (12) | 0.60424 (12) | 0.0182 (4) | |
O4 | 0.3652 (2) | −0.07681 (13) | 0.41864 (12) | 0.0195 (4) | |
O5 | 0.1094 (2) | 0.08860 (15) | 0.11724 (13) | 0.0274 (4) | |
H5 | 0.0469 | 0.1228 | 0.0708 | 0.041* | |
O6 | −0.1608 (2) | 0.27214 (14) | 0.12330 (12) | 0.0200 (4) | |
O7 | 0.05740 (19) | 0.12126 (12) | 0.57138 (11) | 0.0146 (3) | |
O8 | 0.6481 (2) | −0.24864 (13) | 0.40092 (13) | 0.0249 (4) | |
O9 | 0.6536 (3) | −0.47167 (16) | 0.41733 (17) | 0.0427 (5) | |
H1O | −0.090 (4) | 0.220 (2) | 0.910 (2) | 0.027 (8)* | |
H2O | 0.517 (5) | −0.122 (3) | 0.728 (3) | 0.062 (11)* | |
H4O | 0.450 (4) | −0.123 (3) | 0.444 (2) | 0.040 (9)* | |
H6O | −0.239 (4) | 0.326 (3) | 0.135 (2) | 0.031 (8)* | |
C16 | 0.4091 (3) | 0.46256 (18) | 0.17056 (16) | 0.0149 (5) | |
C17 | 0.3806 (3) | 0.36307 (18) | 0.21930 (18) | 0.0186 (5) | |
H17 | 0.4733 | 0.2983 | 0.2247 | 0.022* | |
C18 | 0.2202 (3) | 0.36122 (19) | 0.25797 (18) | 0.0208 (5) | |
H18 | 0.2017 | 0.2950 | 0.2903 | 0.025* | |
C19 | 0.0800 (3) | 0.45767 (19) | 0.25040 (18) | 0.0204 (5) | |
H19 | −0.0308 | 0.4549 | 0.2783 | 0.025* | |
C20 | 0.1020 (3) | 0.55406 (19) | 0.20374 (17) | 0.0179 (5) | |
H20 | 0.0071 | 0.6175 | 0.1989 | 0.021* | |
C21 | 0.2677 (3) | 0.55906 (17) | 0.16251 (16) | 0.0147 (5) | |
C22 | 0.4483 (3) | 0.65692 (18) | 0.07993 (16) | 0.0147 (5) | |
C23 | 0.4775 (3) | 0.75597 (19) | 0.03130 (18) | 0.0196 (5) | |
H23 | 0.3842 | 0.8200 | 0.0234 | 0.024* | |
C24 | 0.6384 (3) | 0.7590 (2) | −0.00378 (18) | 0.0215 (5) | |
H24 | 0.6568 | 0.8252 | −0.0364 | 0.026* | |
C25 | 0.7801 (3) | 0.6638 (2) | 0.00796 (17) | 0.0199 (5) | |
H25 | 0.8920 | 0.6681 | −0.0154 | 0.024* | |
C26 | 0.7580 (3) | 0.56685 (19) | 0.05197 (17) | 0.0181 (5) | |
H26 | 0.8536 | 0.5039 | 0.0576 | 0.022* | |
C27 | 0.5908 (3) | 0.55986 (18) | 0.08967 (16) | 0.0150 (5) | |
N1 | 0.5688 (2) | 0.46411 (15) | 0.13322 (14) | 0.0149 (4) | |
N2 | 0.2888 (2) | 0.65486 (15) | 0.11644 (14) | 0.0154 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0148 (11) | 0.0133 (10) | 0.0147 (11) | −0.0063 (9) | −0.0042 (8) | 0.0022 (8) |
C2 | 0.0152 (11) | 0.0119 (10) | 0.0163 (11) | 0.0005 (9) | −0.0022 (9) | −0.0003 (8) |
C3 | 0.0182 (11) | 0.0161 (11) | 0.0156 (11) | −0.0042 (9) | 0.0004 (9) | −0.0024 (9) |
C4 | 0.0224 (12) | 0.0170 (11) | 0.0118 (11) | −0.0026 (10) | −0.0053 (9) | 0.0000 (9) |
C5 | 0.0153 (11) | 0.0115 (10) | 0.0205 (12) | −0.0023 (9) | −0.0031 (9) | 0.0015 (9) |
C6 | 0.0157 (11) | 0.0112 (10) | 0.0154 (11) | −0.0054 (9) | −0.0014 (8) | 0.0013 (8) |
C7 | 0.0136 (10) | 0.0113 (10) | 0.0197 (12) | −0.0051 (9) | −0.0002 (9) | 0.0010 (8) |
C8 | 0.0158 (11) | 0.0153 (11) | 0.0144 (11) | −0.0058 (9) | 0.0011 (8) | −0.0019 (8) |
C9 | 0.0142 (11) | 0.0140 (10) | 0.0134 (11) | −0.0059 (9) | 0.0015 (8) | −0.0014 (8) |
C10 | 0.0151 (11) | 0.0127 (10) | 0.0156 (11) | −0.0065 (9) | −0.0024 (8) | 0.0014 (8) |
C11 | 0.0118 (10) | 0.0109 (10) | 0.0186 (12) | −0.0028 (9) | 0.0000 (8) | −0.0019 (8) |
C12 | 0.0138 (10) | 0.0153 (10) | 0.0133 (11) | −0.0071 (9) | 0.0034 (8) | −0.0028 (8) |
C13 | 0.0159 (11) | 0.0137 (10) | 0.0156 (11) | −0.0062 (9) | −0.0031 (9) | 0.0035 (8) |
C14 | 0.0123 (10) | 0.0132 (10) | 0.0197 (12) | −0.0018 (9) | −0.0007 (9) | −0.0002 (9) |
C15 | 0.0138 (11) | 0.0159 (11) | 0.0140 (11) | −0.0043 (9) | 0.0014 (8) | −0.0017 (8) |
C28 | 0.0378 (16) | 0.0464 (17) | 0.0280 (15) | −0.0175 (14) | −0.0051 (12) | −0.0140 (13) |
C29 | 0.0353 (15) | 0.0318 (14) | 0.0188 (13) | −0.0003 (12) | −0.0012 (11) | −0.0089 (11) |
C30 | 0.0248 (13) | 0.0246 (13) | 0.0370 (15) | −0.0053 (11) | −0.0113 (11) | 0.0018 (11) |
C31 | 0.0548 (19) | 0.0336 (15) | 0.0351 (16) | −0.0182 (15) | −0.0179 (14) | 0.0064 (12) |
O1 | 0.0240 (9) | 0.0223 (9) | 0.0120 (8) | 0.0066 (8) | −0.0029 (7) | −0.0035 (7) |
O2 | 0.0198 (8) | 0.0200 (8) | 0.0193 (9) | 0.0047 (7) | −0.0055 (7) | −0.0003 (7) |
O3 | 0.0159 (8) | 0.0159 (8) | 0.0194 (8) | 0.0012 (7) | −0.0021 (6) | −0.0016 (6) |
O4 | 0.0187 (8) | 0.0184 (8) | 0.0160 (8) | 0.0041 (7) | −0.0005 (7) | −0.0041 (7) |
O5 | 0.0293 (10) | 0.0296 (10) | 0.0196 (9) | −0.0023 (8) | −0.0035 (7) | −0.0011 (7) |
O6 | 0.0181 (8) | 0.0211 (9) | 0.0145 (8) | 0.0038 (7) | −0.0029 (6) | 0.0017 (7) |
O7 | 0.0151 (8) | 0.0150 (8) | 0.0115 (8) | −0.0006 (6) | −0.0012 (6) | −0.0013 (6) |
O8 | 0.0275 (9) | 0.0192 (8) | 0.0257 (10) | −0.0016 (7) | −0.0032 (7) | −0.0043 (7) |
O9 | 0.0571 (14) | 0.0277 (10) | 0.0485 (13) | −0.0169 (10) | −0.0098 (11) | −0.0060 (9) |
C16 | 0.0169 (11) | 0.0175 (11) | 0.0114 (11) | −0.0049 (9) | −0.0030 (8) | −0.0038 (8) |
C17 | 0.0215 (12) | 0.0139 (11) | 0.0204 (12) | −0.0040 (9) | −0.0046 (9) | −0.0016 (9) |
C18 | 0.0273 (13) | 0.0173 (11) | 0.0198 (12) | −0.0094 (10) | −0.0019 (10) | −0.0016 (9) |
C19 | 0.0190 (12) | 0.0243 (12) | 0.0208 (12) | −0.0103 (10) | −0.0003 (9) | −0.0030 (10) |
C20 | 0.0152 (11) | 0.0188 (11) | 0.0189 (12) | −0.0024 (9) | −0.0013 (9) | −0.0040 (9) |
C21 | 0.0185 (11) | 0.0144 (11) | 0.0122 (11) | −0.0051 (9) | −0.0029 (8) | −0.0022 (8) |
C22 | 0.0151 (11) | 0.0176 (11) | 0.0116 (11) | −0.0038 (9) | −0.0037 (8) | −0.0015 (8) |
C23 | 0.0199 (12) | 0.0181 (11) | 0.0191 (12) | −0.0034 (10) | −0.0039 (9) | 0.0031 (9) |
C24 | 0.0270 (13) | 0.0217 (12) | 0.0184 (12) | −0.0122 (11) | −0.0038 (10) | 0.0041 (9) |
C25 | 0.0184 (12) | 0.0291 (13) | 0.0146 (11) | −0.0108 (10) | −0.0014 (9) | −0.0007 (9) |
C26 | 0.0141 (11) | 0.0248 (12) | 0.0150 (11) | −0.0034 (10) | −0.0024 (9) | −0.0039 (9) |
C27 | 0.0177 (11) | 0.0162 (11) | 0.0105 (11) | −0.0030 (9) | −0.0033 (8) | −0.0019 (8) |
N1 | 0.0153 (9) | 0.0152 (9) | 0.0135 (9) | −0.0024 (8) | −0.0018 (7) | −0.0033 (7) |
N2 | 0.0163 (9) | 0.0166 (9) | 0.0128 (9) | −0.0035 (8) | −0.0014 (7) | −0.0014 (7) |
C1—O7 | 1.363 (3) | C30—O8 | 1.425 (3) |
C1—C2 | 1.391 (3) | C30—C31 | 1.509 (4) |
C1—C6 | 1.396 (3) | C30—H30A | 0.9900 |
C2—C3 | 1.391 (3) | C30—H30B | 0.9900 |
C2—H2 | 0.9500 | C31—O9 | 1.429 (3) |
C3—O1 | 1.360 (3) | C31—H31A | 0.9900 |
C3—C4 | 1.400 (3) | C31—H31B | 0.9900 |
C4—C5 | 1.380 (3) | O1—H1O | 0.81 (3) |
C4—H4 | 0.9500 | O2—H2O | 1.00 (4) |
C5—O2 | 1.354 (3) | O4—H4O | 0.84 (3) |
C5—C6 | 1.419 (3) | O5—H5 | 0.8400 |
C6—C7 | 1.436 (3) | O6—H6O | 0.81 (3) |
C7—O3 | 1.263 (3) | C16—N1 | 1.352 (3) |
C7—C8 | 1.445 (3) | C16—C17 | 1.429 (3) |
C8—C9 | 1.359 (3) | C16—C21 | 1.431 (3) |
C8—O4 | 1.360 (3) | C17—C18 | 1.362 (3) |
C9—O7 | 1.380 (3) | C17—H17 | 0.9500 |
C9—C10 | 1.471 (3) | C18—C19 | 1.425 (3) |
C10—C11 | 1.407 (3) | C18—H18 | 0.9500 |
C10—C15 | 1.409 (3) | C19—C20 | 1.366 (3) |
C11—C12 | 1.388 (3) | C19—H19 | 0.9500 |
C11—H11 | 0.9500 | C20—C21 | 1.422 (3) |
C12—O5 | 1.367 (3) | C20—H20 | 0.9500 |
C12—C13 | 1.399 (3) | C21—N2 | 1.354 (3) |
C13—O6 | 1.368 (3) | C22—N2 | 1.348 (3) |
C13—C14 | 1.393 (3) | C22—C23 | 1.426 (3) |
C14—C15 | 1.385 (3) | C22—C27 | 1.442 (3) |
C14—H14 | 0.9500 | C23—C24 | 1.359 (3) |
C15—H15 | 0.9500 | C23—H23 | 0.9500 |
C28—O9 | 1.420 (4) | C24—C25 | 1.426 (3) |
C28—C29 | 1.507 (4) | C24—H24 | 0.9500 |
C28—H28A | 0.9900 | C25—C26 | 1.361 (3) |
C28—H28B | 0.9900 | C25—H25 | 0.9500 |
C29—O8 | 1.424 (3) | C26—C27 | 1.429 (3) |
C29—H29A | 0.9900 | C26—H26 | 0.9500 |
C29—H29B | 0.9900 | C27—N1 | 1.345 (3) |
O7—C1—C2 | 116.84 (19) | O8—C30—H30A | 109.5 |
O7—C1—C6 | 120.90 (19) | C31—C30—H30A | 109.5 |
C2—C1—C6 | 122.3 (2) | O8—C30—H30B | 109.5 |
C1—C2—C3 | 117.8 (2) | C31—C30—H30B | 109.5 |
C1—C2—H2 | 121.1 | H30A—C30—H30B | 108.0 |
C3—C2—H2 | 121.1 | O9—C31—C30 | 110.8 (2) |
O1—C3—C2 | 122.2 (2) | O9—C31—H31A | 109.5 |
O1—C3—C4 | 115.9 (2) | C30—C31—H31A | 109.5 |
C2—C3—C4 | 122.0 (2) | O9—C31—H31B | 109.5 |
C5—C4—C3 | 119.1 (2) | C30—C31—H31B | 109.5 |
C5—C4—H4 | 120.4 | H31A—C31—H31B | 108.1 |
C3—C4—H4 | 120.4 | C3—O1—H1O | 110 (2) |
O2—C5—C4 | 119.9 (2) | C5—O2—H2O | 105 (2) |
O2—C5—C6 | 119.43 (19) | C8—O4—H4O | 105 (2) |
C4—C5—C6 | 120.6 (2) | C12—O5—H5 | 109.5 |
C1—C6—C5 | 118.1 (2) | C13—O6—H6O | 109 (2) |
C1—C6—C7 | 119.6 (2) | C1—O7—C9 | 121.36 (17) |
C5—C6—C7 | 122.3 (2) | C29—O8—C30 | 110.90 (19) |
O3—C7—C6 | 123.5 (2) | C28—O9—C31 | 108.9 (2) |
O3—C7—C8 | 120.2 (2) | N1—C16—C17 | 119.6 (2) |
C6—C7—C8 | 116.33 (19) | N1—C16—C21 | 121.1 (2) |
C9—C8—O4 | 121.9 (2) | C17—C16—C21 | 119.3 (2) |
C9—C8—C7 | 121.7 (2) | C18—C17—C16 | 119.9 (2) |
O4—C8—C7 | 116.37 (19) | C18—C17—H17 | 120.1 |
C8—C9—O7 | 119.91 (19) | C16—C17—H17 | 120.1 |
C8—C9—C10 | 129.1 (2) | C17—C18—C19 | 120.7 (2) |
O7—C9—C10 | 111.01 (18) | C17—C18—H18 | 119.7 |
C11—C10—C15 | 118.10 (19) | C19—C18—H18 | 119.7 |
C11—C10—C9 | 121.96 (19) | C20—C19—C18 | 121.1 (2) |
C15—C10—C9 | 119.93 (19) | C20—C19—H19 | 119.4 |
C12—C11—C10 | 120.9 (2) | C18—C19—H19 | 119.4 |
C12—C11—H11 | 119.5 | C19—C20—C21 | 119.8 (2) |
C10—C11—H11 | 119.5 | C19—C20—H20 | 120.1 |
O5—C12—C11 | 118.24 (19) | C21—C20—H20 | 120.1 |
O5—C12—C13 | 121.49 (19) | N2—C21—C20 | 119.5 (2) |
C11—C12—C13 | 120.27 (19) | N2—C21—C16 | 121.2 (2) |
O6—C13—C14 | 124.3 (2) | C20—C21—C16 | 119.3 (2) |
O6—C13—C12 | 116.43 (19) | N2—C22—C23 | 120.0 (2) |
C14—C13—C12 | 119.26 (19) | N2—C22—C27 | 120.76 (19) |
C15—C14—C13 | 120.7 (2) | C23—C22—C27 | 119.2 (2) |
C15—C14—H14 | 119.7 | C24—C23—C22 | 120.2 (2) |
C13—C14—H14 | 119.7 | C24—C23—H23 | 119.9 |
C14—C15—C10 | 120.7 (2) | C22—C23—H23 | 119.9 |
C14—C15—H15 | 119.6 | C23—C24—C25 | 120.6 (2) |
C10—C15—H15 | 119.6 | C23—C24—H24 | 119.7 |
O9—C28—C29 | 110.6 (2) | C25—C24—H24 | 119.7 |
O9—C28—H28A | 109.5 | C26—C25—C24 | 121.3 (2) |
C29—C28—H28A | 109.5 | C26—C25—H25 | 119.4 |
O9—C28—H28B | 109.5 | C24—C25—H25 | 119.4 |
C29—C28—H28B | 109.5 | C25—C26—C27 | 119.9 (2) |
H28A—C28—H28B | 108.1 | C25—C26—H26 | 120.0 |
O8—C29—C28 | 110.1 (2) | C27—C26—H26 | 120.0 |
O8—C29—H29A | 109.6 | N1—C27—C26 | 120.0 (2) |
C28—C29—H29A | 109.6 | N1—C27—C22 | 121.34 (19) |
O8—C29—H29B | 109.6 | C26—C27—C22 | 118.7 (2) |
C28—C29—H29B | 109.6 | C27—N1—C16 | 117.73 (19) |
H29A—C29—H29B | 108.2 | C22—N2—C21 | 117.79 (19) |
O8—C30—C31 | 110.9 (2) |
C33H22N3O7 | V = 1293.9 (7) Å3 |
Mr = 572.53 | Z = 2 |
Triclinic, P1 | F(000) = 594 |
a = 8.416 (3) Å | Dx = 1.470 Mg m−3 |
b = 12.297 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 13.111 (4) Å | µ = 0.11 mm−1 |
α = 87.100 (6)° | T = 150 K |
β = 84.103 (6)° | Plate, yellow-red |
γ = 73.503 (5)° | 0.30 × 0.20 × 0.10 mm |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | Rint = 0.128 |
Tmin = 0.462, Tmax = 1.000 | θmax = 26.0°, θmin = 3.1° |
10572 measured reflections | h = −10→10 |
5028 independent reflections | k = −15→15 |
2322 reflections with I > 2σ(I) | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.216 | w = 1/[σ2(Fo2) + (0.0866P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
5028 reflections | Δρmax = 0.33 e Å−3 |
402 parameters | Δρmin = −0.30 e Å−3 |
C33H22N3O7 | γ = 73.503 (5)° |
Mr = 572.53 | V = 1293.9 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.416 (3) Å | Mo Kα radiation |
b = 12.297 (4) Å | µ = 0.11 mm−1 |
c = 13.111 (4) Å | T = 150 K |
α = 87.100 (6)° | 0.30 × 0.20 × 0.10 mm |
β = 84.103 (6)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 5028 independent reflections |
Tmin = 0.462, Tmax = 1.000 | 2322 reflections with I > 2σ(I) |
10572 measured reflections | Rint = 0.128 |
R[F2 > 2σ(F2)] = 0.085 | 0 restraints |
wR(F2) = 0.216 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.33 e Å−3 |
5028 reflections | Δρmin = −0.30 e Å−3 |
402 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
H1O | 0.608 (7) | 0.273 (5) | 0.588 (4) | 0.059 (19)* | |
H5O | 0.465 (9) | 0.376 (6) | 1.447 (5) | 0.12 (3)* | |
H6A | 0.753 (8) | 0.164 (6) | 1.357 (5) | 0.09 (2)* | |
O7 | 0.4485 (3) | 0.3777 (2) | 0.9315 (2) | 0.0216 (7) | |
O2 | 0.0355 (4) | 0.5931 (3) | 0.7176 (2) | 0.0317 (9) | |
H2O | −0.0032 | 0.6245 | 0.7737 | 0.048* | |
O3 | 0.0175 (4) | 0.6321 (3) | 0.9162 (2) | 0.0285 (8) | |
O4 | 0.1385 (4) | 0.5753 (3) | 1.0968 (2) | 0.0321 (9) | |
H4O | 0.0450 | 0.6155 | 1.0814 | 0.048* | |
C9 | 0.3627 (5) | 0.4291 (4) | 1.0205 (3) | 0.0211 (11) | |
O1 | 0.5157 (4) | 0.3297 (3) | 0.5729 (2) | 0.0287 (8) | |
O5 | 0.3928 (4) | 0.4082 (3) | 1.3895 (2) | 0.0294 (9) | |
C6 | 0.2395 (5) | 0.4920 (4) | 0.8285 (3) | 0.0216 (11) | |
O6 | 0.6626 (4) | 0.2241 (3) | 1.3736 (2) | 0.0295 (9) | |
C8 | 0.2236 (5) | 0.5184 (4) | 1.0134 (3) | 0.0212 (11) | |
C7 | 0.1519 (6) | 0.5522 (4) | 0.9176 (3) | 0.0224 (11) | |
C4 | 0.2764 (6) | 0.4594 (4) | 0.6462 (3) | 0.0254 (11) | |
H4 | 0.2376 | 0.4753 | 0.5800 | 0.030* | |
C2 | 0.4861 (6) | 0.3525 (4) | 0.7548 (3) | 0.0246 (11) | |
H2 | 0.5895 | 0.2977 | 0.7630 | 0.030* | |
C1 | 0.3881 (5) | 0.4081 (4) | 0.8385 (3) | 0.0201 (11) | |
C10 | 0.4430 (5) | 0.3759 (4) | 1.1112 (3) | 0.0202 (10) | |
C11 | 0.3811 (5) | 0.4160 (4) | 1.2097 (3) | 0.0216 (11) | |
H11 | 0.2849 | 0.4791 | 1.2179 | 0.026* | |
C3 | 0.4288 (6) | 0.3793 (4) | 0.6586 (3) | 0.0232 (11) | |
C14 | 0.6605 (5) | 0.2300 (4) | 1.1875 (3) | 0.0233 (11) | |
H14 | 0.7561 | 0.1664 | 1.1802 | 0.028* | |
C12 | 0.4583 (6) | 0.3650 (4) | 1.2957 (4) | 0.0264 (12) | |
C13 | 0.5969 (6) | 0.2710 (4) | 1.2846 (3) | 0.0231 (11) | |
C15 | 0.5849 (5) | 0.2816 (4) | 1.1008 (3) | 0.0237 (11) | |
H15 | 0.6291 | 0.2531 | 1.0347 | 0.028* | |
C5 | 0.1830 (5) | 0.5151 (4) | 0.7295 (4) | 0.0238 (11) | |
N1 | 0.2106 (5) | 0.8424 (3) | 0.3883 (3) | 0.0252 (9) | |
N2 | −0.0679 (4) | 1.0300 (3) | 0.3575 (3) | 0.0240 (9) | |
C27 | 0.0550 (6) | 0.8398 (4) | 0.4213 (3) | 0.0233 (11) | |
C16 | 0.2277 (5) | 0.9387 (4) | 0.3393 (3) | 0.0231 (11) | |
C22 | −0.0865 (5) | 0.9342 (4) | 0.4056 (3) | 0.0238 (11) | |
C20 | 0.1122 (6) | 1.1317 (4) | 0.2709 (4) | 0.0288 (12) | |
H20 | 0.0192 | 1.1944 | 0.2588 | 0.035* | |
C17 | 0.3901 (6) | 0.9463 (4) | 0.3036 (3) | 0.0258 (11) | |
H17 | 0.4847 | 0.8840 | 0.3137 | 0.031* | |
C26 | 0.0322 (6) | 0.7403 (4) | 0.4742 (3) | 0.0295 (12) | |
H26 | 0.1254 | 0.6776 | 0.4860 | 0.035* | |
C19 | 0.2677 (6) | 1.1365 (4) | 0.2389 (4) | 0.0300 (12) | |
H19 | 0.2830 | 1.2034 | 0.2050 | 0.036* | |
C21 | 0.0879 (6) | 1.0329 (4) | 0.3226 (3) | 0.0245 (11) | |
C23 | −0.2471 (6) | 0.9268 (4) | 0.4426 (4) | 0.0298 (12) | |
H23 | −0.3416 | 0.9894 | 0.4336 | 0.036* | |
C18 | 0.4097 (6) | 1.0429 (4) | 0.2549 (4) | 0.0315 (12) | |
H18 | 0.5181 | 1.0480 | 0.2315 | 0.038* | |
C24 | −0.2666 (6) | 0.8299 (4) | 0.4913 (4) | 0.0319 (13) | |
H24 | −0.3750 | 0.8247 | 0.5144 | 0.038* | |
C25 | −0.1249 (6) | 0.7361 (4) | 0.5076 (4) | 0.0312 (12) | |
H25 | −0.1404 | 0.6697 | 0.5423 | 0.037* | |
N3 | 0.1260 (5) | 0.9545 (3) | 0.0688 (3) | 0.0348 (11) | |
C31 | −0.0139 (6) | 0.9216 (4) | 0.0732 (4) | 0.0280 (12) | |
C30 | 0.1414 (6) | 1.0338 (4) | −0.0059 (4) | 0.0325 (13) | |
C29 | 0.2838 (6) | 1.0727 (4) | −0.0141 (4) | 0.0351 (13) | |
H29 | 0.3671 | 1.0444 | 0.0319 | 0.042* | |
C32 | −0.0385 (6) | 0.8392 (4) | 0.1503 (4) | 0.0334 (13) | |
H32 | 0.0435 | 0.8086 | 0.1966 | 0.040* | |
C33 | −0.1775 (6) | 0.8054 (4) | 0.1569 (4) | 0.0359 (13) | |
H33 | −0.1929 | 0.7514 | 0.2085 | 0.043* | |
C28 | 0.3025 (6) | 1.1513 (5) | −0.0882 (4) | 0.0395 (14) | |
H28 | 0.3992 | 1.1773 | −0.0940 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O7 | 0.0233 (18) | 0.0189 (18) | 0.0205 (18) | −0.0033 (14) | −0.0022 (14) | 0.0032 (14) |
O2 | 0.026 (2) | 0.024 (2) | 0.039 (2) | 0.0032 (15) | −0.0079 (16) | 0.0038 (16) |
O3 | 0.0212 (18) | 0.023 (2) | 0.036 (2) | 0.0022 (15) | −0.0019 (15) | 0.0014 (15) |
O4 | 0.026 (2) | 0.033 (2) | 0.029 (2) | 0.0047 (16) | −0.0017 (15) | −0.0004 (16) |
C9 | 0.025 (3) | 0.021 (3) | 0.019 (3) | −0.010 (2) | 0.000 (2) | 0.001 (2) |
O1 | 0.031 (2) | 0.027 (2) | 0.023 (2) | 0.0003 (17) | −0.0023 (16) | 0.0028 (15) |
O5 | 0.029 (2) | 0.035 (2) | 0.022 (2) | −0.0062 (16) | 0.0027 (16) | −0.0013 (16) |
C6 | 0.020 (3) | 0.027 (3) | 0.019 (3) | −0.008 (2) | −0.003 (2) | 0.004 (2) |
O6 | 0.028 (2) | 0.032 (2) | 0.0223 (19) | 0.0005 (17) | −0.0024 (16) | 0.0047 (16) |
C8 | 0.020 (3) | 0.022 (3) | 0.020 (3) | −0.005 (2) | 0.005 (2) | −0.003 (2) |
C7 | 0.024 (3) | 0.016 (3) | 0.029 (3) | −0.008 (2) | −0.005 (2) | 0.005 (2) |
C4 | 0.030 (3) | 0.023 (3) | 0.022 (3) | −0.005 (2) | −0.008 (2) | 0.006 (2) |
C2 | 0.028 (3) | 0.022 (3) | 0.025 (3) | −0.008 (2) | −0.004 (2) | 0.004 (2) |
C1 | 0.021 (3) | 0.016 (3) | 0.024 (3) | −0.006 (2) | −0.006 (2) | 0.005 (2) |
C10 | 0.020 (3) | 0.017 (3) | 0.025 (3) | −0.008 (2) | −0.003 (2) | 0.004 (2) |
C11 | 0.020 (3) | 0.018 (3) | 0.025 (3) | −0.006 (2) | 0.000 (2) | 0.005 (2) |
C3 | 0.025 (3) | 0.024 (3) | 0.022 (3) | −0.010 (2) | 0.003 (2) | 0.000 (2) |
C14 | 0.022 (3) | 0.022 (3) | 0.025 (3) | −0.007 (2) | −0.003 (2) | 0.003 (2) |
C12 | 0.024 (3) | 0.036 (3) | 0.022 (3) | −0.015 (2) | 0.002 (2) | −0.001 (2) |
C13 | 0.030 (3) | 0.024 (3) | 0.018 (3) | −0.012 (2) | −0.004 (2) | 0.006 (2) |
C15 | 0.025 (3) | 0.023 (3) | 0.023 (3) | −0.006 (2) | −0.004 (2) | 0.001 (2) |
C5 | 0.024 (3) | 0.016 (3) | 0.029 (3) | −0.001 (2) | −0.002 (2) | −0.001 (2) |
N1 | 0.030 (2) | 0.024 (2) | 0.024 (2) | −0.0100 (18) | −0.0045 (18) | 0.0035 (18) |
N2 | 0.021 (2) | 0.027 (2) | 0.022 (2) | −0.0042 (18) | −0.0002 (17) | −0.0019 (18) |
C27 | 0.028 (3) | 0.024 (3) | 0.020 (3) | −0.010 (2) | −0.001 (2) | 0.004 (2) |
C16 | 0.023 (3) | 0.023 (3) | 0.021 (3) | −0.003 (2) | 0.000 (2) | 0.001 (2) |
C22 | 0.021 (3) | 0.024 (3) | 0.024 (3) | −0.003 (2) | −0.001 (2) | −0.001 (2) |
C20 | 0.028 (3) | 0.020 (3) | 0.037 (3) | −0.005 (2) | −0.002 (2) | 0.002 (2) |
C17 | 0.021 (3) | 0.018 (3) | 0.034 (3) | 0.000 (2) | 0.002 (2) | −0.001 (2) |
C26 | 0.032 (3) | 0.023 (3) | 0.032 (3) | −0.005 (2) | −0.010 (2) | 0.010 (2) |
C19 | 0.035 (3) | 0.019 (3) | 0.035 (3) | −0.010 (2) | 0.004 (2) | −0.001 (2) |
C21 | 0.027 (3) | 0.018 (3) | 0.028 (3) | −0.005 (2) | −0.005 (2) | 0.004 (2) |
C23 | 0.023 (3) | 0.031 (3) | 0.032 (3) | −0.001 (2) | −0.006 (2) | 0.003 (2) |
C18 | 0.032 (3) | 0.025 (3) | 0.038 (3) | −0.010 (2) | 0.004 (2) | −0.003 (2) |
C24 | 0.024 (3) | 0.036 (3) | 0.036 (3) | −0.013 (2) | 0.003 (2) | 0.001 (2) |
C25 | 0.031 (3) | 0.034 (3) | 0.031 (3) | −0.013 (2) | −0.006 (2) | 0.007 (2) |
N3 | 0.034 (3) | 0.034 (3) | 0.035 (3) | −0.006 (2) | −0.004 (2) | −0.002 (2) |
C31 | 0.025 (3) | 0.025 (3) | 0.031 (3) | −0.002 (2) | 0.000 (2) | 0.002 (2) |
C30 | 0.029 (3) | 0.025 (3) | 0.042 (3) | −0.005 (2) | −0.005 (2) | 0.001 (2) |
C29 | 0.023 (3) | 0.041 (4) | 0.040 (3) | −0.006 (2) | 0.003 (2) | −0.006 (3) |
C32 | 0.035 (3) | 0.027 (3) | 0.032 (3) | −0.002 (2) | 0.004 (2) | 0.003 (2) |
C33 | 0.043 (3) | 0.024 (3) | 0.039 (3) | −0.011 (3) | 0.006 (3) | 0.000 (2) |
C28 | 0.032 (3) | 0.041 (4) | 0.045 (4) | −0.014 (3) | 0.004 (3) | −0.002 (3) |
O7—C1 | 1.364 (5) | N2—C22 | 1.349 (6) |
O7—C9 | 1.387 (5) | N2—C21 | 1.354 (5) |
O2—C5 | 1.354 (5) | C27—C26 | 1.427 (6) |
O2—H2O | 0.8400 | C27—C22 | 1.432 (6) |
O3—C7 | 1.271 (5) | C16—C21 | 1.424 (6) |
O4—C8 | 1.353 (5) | C16—C17 | 1.426 (6) |
O4—H4O | 0.8400 | C22—C23 | 1.415 (6) |
C9—C8 | 1.367 (6) | C20—C19 | 1.349 (6) |
C9—C10 | 1.461 (6) | C20—C21 | 1.416 (6) |
O1—C3 | 1.348 (5) | C20—H20 | 0.9500 |
O1—H1O | 0.91 (6) | C17—C18 | 1.364 (6) |
O5—C12 | 1.363 (5) | C17—H17 | 0.9500 |
O5—H5O | 1.01 (7) | C26—C25 | 1.364 (6) |
C6—C1 | 1.391 (6) | C26—H26 | 0.9500 |
C6—C5 | 1.415 (6) | C19—C18 | 1.430 (7) |
C6—C7 | 1.434 (6) | C19—H19 | 0.9500 |
O6—C13 | 1.373 (5) | C23—C24 | 1.367 (6) |
O6—H6A | 0.92 (7) | C23—H23 | 0.9500 |
C8—C7 | 1.441 (6) | C18—H18 | 0.9500 |
C4—C5 | 1.368 (6) | C24—C25 | 1.430 (7) |
C4—C3 | 1.397 (6) | C24—H24 | 0.9500 |
C4—H4 | 0.9500 | C25—H25 | 0.9500 |
C2—C1 | 1.386 (6) | N3—C31 | 1.344 (6) |
C2—C3 | 1.388 (6) | N3—C30 | 1.369 (6) |
C2—H2 | 0.9500 | C31—C30i | 1.430 (6) |
C10—C11 | 1.401 (6) | C31—C32 | 1.436 (6) |
C10—C15 | 1.409 (6) | C30—C29 | 1.404 (6) |
C11—C12 | 1.391 (6) | C30—C31i | 1.430 (6) |
C11—H11 | 0.9500 | C29—C28 | 1.365 (7) |
C14—C13 | 1.390 (6) | C29—H29 | 0.9500 |
C14—C15 | 1.395 (6) | C32—C33 | 1.341 (6) |
C14—H14 | 0.9500 | C32—H32 | 0.9500 |
C12—C13 | 1.390 (6) | C33—C28i | 1.424 (7) |
C15—H15 | 0.9500 | C33—H33 | 0.9500 |
N1—C27 | 1.345 (5) | C28—C33i | 1.424 (7) |
N1—C16 | 1.354 (6) | C28—H28 | 0.9500 |
C1—O7—C9 | 121.0 (3) | N1—C27—C22 | 121.7 (4) |
C5—O2—H2O | 109.5 | C26—C27—C22 | 119.7 (4) |
C8—O4—H4O | 109.5 | N1—C16—C21 | 121.9 (4) |
C8—C9—O7 | 119.2 (4) | N1—C16—C17 | 119.3 (4) |
C8—C9—C10 | 129.6 (4) | C21—C16—C17 | 118.9 (4) |
O7—C9—C10 | 111.2 (4) | N2—C22—C23 | 120.0 (4) |
C3—O1—H1O | 111 (3) | N2—C22—C27 | 120.8 (4) |
C12—O5—H5O | 114 (4) | C23—C22—C27 | 119.2 (4) |
C1—C6—C5 | 117.9 (4) | C19—C20—C21 | 119.8 (4) |
C1—C6—C7 | 119.1 (4) | C19—C20—H20 | 120.1 |
C5—C6—C7 | 123.0 (4) | C21—C20—H20 | 120.1 |
C13—O6—H6A | 108 (4) | C18—C17—C16 | 120.0 (4) |
O4—C8—C9 | 122.1 (4) | C18—C17—H17 | 120.0 |
O4—C8—C7 | 115.9 (4) | C16—C17—H17 | 120.0 |
C9—C8—C7 | 121.9 (4) | C25—C26—C27 | 119.2 (4) |
O3—C7—C6 | 124.0 (4) | C25—C26—H26 | 120.4 |
O3—C7—C8 | 119.3 (4) | C27—C26—H26 | 120.4 |
C6—C7—C8 | 116.7 (4) | C20—C19—C18 | 121.3 (5) |
C5—C4—C3 | 120.0 (4) | C20—C19—H19 | 119.3 |
C5—C4—H4 | 120.0 | C18—C19—H19 | 119.3 |
C3—C4—H4 | 120.0 | N2—C21—C20 | 119.6 (4) |
C1—C2—C3 | 118.1 (4) | N2—C21—C16 | 120.6 (4) |
C1—C2—H2 | 121.0 | C20—C21—C16 | 119.8 (4) |
C3—C2—H2 | 121.0 | C24—C23—C22 | 120.2 (4) |
O7—C1—C2 | 115.9 (4) | C24—C23—H23 | 119.9 |
O7—C1—C6 | 121.7 (4) | C22—C23—H23 | 119.9 |
C2—C1—C6 | 122.3 (4) | C17—C18—C19 | 120.2 (4) |
C11—C10—C15 | 118.6 (4) | C17—C18—H18 | 119.9 |
C11—C10—C9 | 121.3 (4) | C19—C18—H18 | 119.9 |
C15—C10—C9 | 120.0 (4) | C23—C24—C25 | 120.4 (4) |
C12—C11—C10 | 121.0 (4) | C23—C24—H24 | 119.8 |
C12—C11—H11 | 119.5 | C25—C24—H24 | 119.8 |
C10—C11—H11 | 119.5 | C26—C25—C24 | 121.2 (5) |
O1—C3—C2 | 122.2 (4) | C26—C25—H25 | 119.4 |
O1—C3—C4 | 116.7 (4) | C24—C25—H25 | 119.4 |
C2—C3—C4 | 121.1 (4) | C31—N3—C30 | 115.9 (4) |
C13—C14—C15 | 120.4 (4) | N3—C31—C30i | 123.1 (4) |
C13—C14—H14 | 119.8 | N3—C31—C32 | 118.8 (4) |
C15—C14—H14 | 119.8 | C30i—C31—C32 | 118.1 (4) |
O5—C12—C13 | 121.8 (4) | N3—C30—C29 | 118.8 (5) |
O5—C12—C11 | 118.3 (4) | N3—C30—C31i | 121.0 (4) |
C13—C12—C11 | 119.8 (4) | C29—C30—C31i | 120.2 (5) |
O6—C13—C12 | 116.0 (4) | C28—C29—C30 | 119.9 (5) |
O6—C13—C14 | 123.9 (4) | C28—C29—H29 | 120.0 |
C12—C13—C14 | 120.1 (4) | C30—C29—H29 | 120.0 |
C14—C15—C10 | 120.1 (4) | C33—C32—C31 | 120.0 (5) |
C14—C15—H15 | 120.0 | C33—C32—H32 | 120.0 |
C10—C15—H15 | 120.0 | C31—C32—H32 | 120.0 |
O2—C5—C4 | 120.0 (4) | C32—C33—C28i | 121.5 (5) |
O2—C5—C6 | 119.5 (4) | C32—C33—H33 | 119.2 |
C4—C5—C6 | 120.5 (4) | C28i—C33—H33 | 119.2 |
C27—N1—C16 | 117.0 (4) | C29—C28—C33i | 120.3 (5) |
C22—N2—C21 | 117.9 (4) | C29—C28—H28 | 119.9 |
N1—C27—C26 | 118.6 (4) | C33i—C28—H28 | 119.9 |
Symmetry code: (i) −x, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4 | 0.95 | 2.20 | 2.873 (5) | 127 |
C20—H20···O2ii | 0.95 | 2.55 | 3.263 (6) | 132 |
Symmetry code: (ii) −x, −y+2, −z+1. |
C58H42N7O8 | V = 2313.09 (12) Å3 |
Mr = 964.98 | Z = 2 |
Triclinic, P1 | F(000) = 1006 |
a = 9.9945 (3) Å | Dx = 1.385 Mg m−3 |
b = 13.4346 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 17.8220 (5) Å | µ = 0.09 mm−1 |
α = 81.016 (1)° | T = 150 K |
β = 78.335 (1)° | Plate, light yellow |
γ = 86.046 (1)° | 0.25 × 0.22 × 0.10 mm |
Absorption correction: analytical Bruker, AXS, 2008 | Rint = 0.033 |
Tmin = 0.977, Tmax = 0.991 | θmax = 27.5°, θmin = 1.2° |
29578 measured reflections | h = −12→12 |
10501 independent reflections | k = −14→17 |
7634 reflections with I > 2σ(I) | l = −23→23 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0529P)2 + 0.6577P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
10501 reflections | Δρmax = 0.36 e Å−3 |
683 parameters | Δρmin = −0.37 e Å−3 |
C58H42N7O8 | γ = 86.046 (1)° |
Mr = 964.98 | V = 2313.09 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.9945 (3) Å | Mo Kα radiation |
b = 13.4346 (4) Å | µ = 0.09 mm−1 |
c = 17.8220 (5) Å | T = 150 K |
α = 81.016 (1)° | 0.25 × 0.22 × 0.10 mm |
β = 78.335 (1)° |
Absorption correction: analytical Bruker, AXS, 2008 | 10501 independent reflections |
Tmin = 0.977, Tmax = 0.991 | 7634 reflections with I > 2σ(I) |
29578 measured reflections | Rint = 0.033 |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.36 e Å−3 |
10501 reflections | Δρmin = −0.37 e Å−3 |
683 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O7 | 0.07817 (9) | 0.81970 (7) | 0.42805 (5) | 0.0181 (2) | |
O3 | −0.24191 (10) | 1.00375 (8) | 0.37618 (6) | 0.0241 (2) | |
C6 | −0.12137 (14) | 0.92118 (10) | 0.47164 (8) | 0.0166 (3) | |
O2 | −0.31966 (11) | 1.01790 (8) | 0.52421 (7) | 0.0273 (3) | |
O1 | −0.05704 (12) | 0.83949 (9) | 0.69569 (6) | 0.0276 (3) | |
O4 | −0.06720 (12) | 0.92229 (9) | 0.26132 (6) | 0.0290 (3) | |
N5 | −0.22440 (12) | 1.06130 (9) | 0.18882 (7) | 0.0203 (3) | |
C9 | 0.06047 (14) | 0.84258 (10) | 0.35280 (8) | 0.0168 (3) | |
N6 | −0.36749 (13) | 1.20387 (9) | 0.09700 (7) | 0.0235 (3) | |
O5 | 0.29284 (12) | 0.79033 (8) | 0.09083 (6) | 0.0279 (3) | |
C2 | 0.01459 (14) | 0.82614 (10) | 0.56068 (8) | 0.0191 (3) | |
H2 | 0.0900 | 0.7818 | 0.5694 | 0.023* | |
C8 | −0.04648 (14) | 0.90389 (10) | 0.33513 (8) | 0.0185 (3) | |
C47 | −0.16195 (15) | 1.14155 (11) | 0.14395 (8) | 0.0210 (3) | |
C1 | −0.01091 (14) | 0.85667 (10) | 0.48666 (8) | 0.0167 (3) | |
C10 | 0.16565 (14) | 0.79281 (10) | 0.29999 (8) | 0.0169 (3) | |
C4 | −0.18699 (15) | 0.92750 (11) | 0.60948 (9) | 0.0211 (3) | |
H4 | −0.2467 | 0.9513 | 0.6521 | 0.025* | |
C7 | −0.14360 (14) | 0.94771 (10) | 0.39377 (8) | 0.0181 (3) | |
O6 | 0.46858 (12) | 0.64891 (9) | 0.15263 (7) | 0.0331 (3) | |
C11 | 0.17733 (14) | 0.81543 (10) | 0.21929 (8) | 0.0189 (3) | |
H11 | 0.1145 | 0.8629 | 0.1985 | 0.023* | |
C5 | −0.21052 (14) | 0.95619 (10) | 0.53561 (9) | 0.0197 (3) | |
C14 | 0.35853 (15) | 0.67451 (11) | 0.27892 (9) | 0.0223 (3) | |
H14 | 0.4202 | 0.6258 | 0.2994 | 0.027* | |
C53 | −0.42871 (15) | 1.12301 (11) | 0.14078 (8) | 0.0212 (3) | |
C52 | −0.23538 (16) | 1.21488 (11) | 0.09856 (8) | 0.0226 (3) | |
C48 | −0.02160 (16) | 1.15438 (12) | 0.14268 (9) | 0.0269 (3) | |
H48 | 0.0286 | 1.1051 | 0.1713 | 0.032* | |
C3 | −0.07463 (15) | 0.86297 (11) | 0.62157 (8) | 0.0198 (3) | |
C57 | −0.42715 (16) | 0.96908 (11) | 0.23659 (9) | 0.0248 (3) | |
H57 | −0.3809 | 0.9222 | 0.2692 | 0.030* | |
C58 | −0.35651 (15) | 1.05143 (11) | 0.18868 (8) | 0.0200 (3) | |
C51 | −0.16623 (18) | 1.30110 (12) | 0.05543 (9) | 0.0302 (4) | |
H51 | −0.2134 | 1.3511 | 0.0256 | 0.036* | |
C13 | 0.37011 (15) | 0.69763 (11) | 0.19930 (9) | 0.0220 (3) | |
C54 | −0.56853 (16) | 1.10739 (12) | 0.14157 (10) | 0.0285 (4) | |
H54 | −0.6176 | 1.1532 | 0.1098 | 0.034* | |
C12 | 0.27845 (15) | 0.76978 (11) | 0.16984 (8) | 0.0202 (3) | |
C15 | 0.25874 (14) | 0.72113 (10) | 0.32890 (8) | 0.0195 (3) | |
H15 | 0.2530 | 0.7046 | 0.3832 | 0.023* | |
C56 | −0.56053 (17) | 0.95732 (12) | 0.23574 (10) | 0.0286 (4) | |
H56 | −0.6069 | 0.9018 | 0.2676 | 0.034* | |
C49 | 0.04074 (17) | 1.23775 (13) | 0.10024 (10) | 0.0324 (4) | |
H49 | 0.1345 | 1.2464 | 0.0996 | 0.039* | |
C50 | −0.03283 (19) | 1.31184 (13) | 0.05699 (10) | 0.0346 (4) | |
H50 | 0.0121 | 1.3700 | 0.0286 | 0.041* | |
C55 | −0.63190 (16) | 1.02723 (13) | 0.18765 (10) | 0.0317 (4) | |
H55 | −0.7253 | 1.0176 | 0.1878 | 0.038* | |
N7 | 0.08475 (13) | 0.93370 (9) | 0.04197 (7) | 0.0222 (3) | |
C42 | 0.13427 (15) | 1.01710 (11) | −0.00516 (8) | 0.0215 (3) | |
C41 | −0.04793 (16) | 0.91606 (11) | 0.04806 (8) | 0.0215 (3) | |
C43 | 0.27333 (16) | 1.04060 (12) | −0.01245 (9) | 0.0262 (3) | |
H43 | 0.3313 | 0.9970 | 0.0153 | 0.031* | |
C46 | 0.10640 (17) | 1.17029 (11) | −0.09749 (9) | 0.0269 (3) | |
H46 | 0.0518 | 1.2142 | −0.1273 | 0.032* | |
C44 | 0.32363 (17) | 1.12514 (13) | −0.05890 (10) | 0.0300 (4) | |
H44 | 0.4161 | 1.1409 | −0.0624 | 0.036* | |
C45 | 0.23947 (18) | 1.19040 (12) | −0.10240 (10) | 0.0301 (4) | |
H45 | 0.2768 | 1.2486 | −0.1352 | 0.036* | |
N1 | 0.54828 (13) | 0.50516 (9) | 0.38706 (7) | 0.0235 (3) | |
N2 | 0.72307 (13) | 0.37192 (10) | 0.46759 (8) | 0.0252 (3) | |
C28 | 0.50464 (15) | 0.41791 (11) | 0.42954 (8) | 0.0206 (3) | |
C40 | 0.67865 (15) | 0.52667 (11) | 0.38428 (9) | 0.0234 (3) | |
C33 | 0.59325 (15) | 0.35008 (11) | 0.46956 (9) | 0.0214 (3) | |
C32 | 0.54195 (17) | 0.25686 (12) | 0.51170 (9) | 0.0289 (4) | |
H32 | 0.5996 | 0.2109 | 0.5380 | 0.035* | |
C29 | 0.36727 (16) | 0.39064 (12) | 0.43466 (9) | 0.0273 (4) | |
H29 | 0.3068 | 0.4352 | 0.4094 | 0.033* | |
C34 | 0.76627 (15) | 0.46002 (12) | 0.42535 (9) | 0.0241 (3) | |
C30 | 0.32281 (17) | 0.30115 (13) | 0.47554 (10) | 0.0333 (4) | |
H30 | 0.2314 | 0.2834 | 0.4783 | 0.040* | |
C35 | 0.90340 (17) | 0.48781 (14) | 0.42065 (11) | 0.0362 (4) | |
H35 | 0.9626 | 0.4450 | 0.4481 | 0.043* | |
C39 | 0.73211 (19) | 0.61743 (13) | 0.33847 (10) | 0.0334 (4) | |
H39 | 0.6757 | 0.6619 | 0.3102 | 0.040* | |
C31 | 0.41128 (18) | 0.23370 (13) | 0.51425 (10) | 0.0340 (4) | |
H31 | 0.3782 | 0.1713 | 0.5424 | 0.041* | |
C38 | 0.8637 (2) | 0.64012 (14) | 0.33535 (11) | 0.0409 (5) | |
H38 | 0.8986 | 0.7005 | 0.3047 | 0.049* | |
C36 | 0.94923 (19) | 0.57521 (15) | 0.37702 (12) | 0.0439 (5) | |
H36 | 1.0405 | 0.5931 | 0.3744 | 0.053* | |
N4 | 0.87871 (13) | 0.32241 (9) | 0.27488 (7) | 0.0229 (3) | |
N3 | 0.76021 (15) | 0.48138 (10) | 0.18205 (8) | 0.0300 (3) | |
C22 | 0.95130 (16) | 0.40228 (11) | 0.23677 (9) | 0.0247 (3) | |
C16 | 0.68718 (16) | 0.40339 (11) | 0.22180 (9) | 0.0259 (3) | |
C20 | 0.66693 (16) | 0.23822 (12) | 0.30615 (9) | 0.0260 (3) | |
H20 | 0.7061 | 0.1835 | 0.3362 | 0.031* | |
C21 | 0.74720 (15) | 0.32141 (11) | 0.26816 (8) | 0.0216 (3) | |
C17 | 0.54755 (18) | 0.39920 (13) | 0.21709 (10) | 0.0337 (4) | |
H17 | 0.5056 | 0.4530 | 0.1876 | 0.040* | |
C18 | 0.47397 (17) | 0.31903 (13) | 0.25438 (11) | 0.0350 (4) | |
H18 | 0.3808 | 0.3172 | 0.2505 | 0.042* | |
C27 | 0.89134 (17) | 0.48104 (12) | 0.18894 (9) | 0.0281 (4) | |
C26 | 0.9753 (2) | 0.56071 (12) | 0.14650 (10) | 0.0365 (4) | |
H26 | 0.9379 | 0.6128 | 0.1133 | 0.044* | |
C19 | 0.53373 (17) | 0.23720 (13) | 0.29943 (10) | 0.0308 (4) | |
H19 | 0.4801 | 0.1816 | 0.3249 | 0.037* | |
C24 | 1.16527 (18) | 0.48670 (14) | 0.20251 (11) | 0.0386 (4) | |
H24 | 1.2576 | 0.4904 | 0.2075 | 0.046* | |
C23 | 1.08998 (17) | 0.40816 (13) | 0.24301 (10) | 0.0325 (4) | |
H23 | 1.1303 | 0.3571 | 0.2756 | 0.039* | |
C25 | 1.1075 (2) | 0.56284 (13) | 0.15306 (11) | 0.0398 (4) | |
H25 | 1.1623 | 0.6161 | 0.1241 | 0.048* | |
O8 | 0.50365 (18) | 0.66108 (13) | 0.00225 (8) | 0.0706 (6) | |
C73 | 0.61460 (19) | 0.60750 (15) | −0.03422 (12) | 0.0444 (5) | |
H73A | 0.6637 | 0.6510 | −0.0792 | 0.067* | |
H73B | 0.5826 | 0.5490 | −0.0512 | 0.067* | |
H73C | 0.6760 | 0.5846 | 0.0020 | 0.067* | |
H5O | 0.223 (2) | 0.8338 (15) | 0.0788 (12) | 0.050 (6)* | |
H4O | −0.126 (2) | 0.9714 (16) | 0.2540 (12) | 0.056 (7)* | |
H6O | 0.466 (2) | 0.6644 (17) | 0.1026 (14) | 0.063 (7)* | |
H2O | −0.316 (2) | 1.0283 (17) | 0.4725 (13) | 0.063 (7)* | |
H1O | 0.011 (2) | 0.7933 (16) | 0.6978 (12) | 0.051 (6)* | |
H8O | 0.463 (2) | 0.7007 (18) | −0.0293 (13) | 0.065 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O7 | 0.0199 (5) | 0.0197 (5) | 0.0146 (5) | 0.0030 (4) | −0.0061 (4) | −0.0003 (4) |
O3 | 0.0251 (5) | 0.0243 (6) | 0.0223 (6) | 0.0086 (4) | −0.0091 (4) | 0.0000 (4) |
C6 | 0.0196 (7) | 0.0123 (6) | 0.0180 (7) | −0.0018 (5) | −0.0058 (6) | 0.0003 (5) |
O2 | 0.0285 (6) | 0.0281 (6) | 0.0244 (6) | 0.0123 (5) | −0.0076 (5) | −0.0035 (5) |
O1 | 0.0331 (6) | 0.0329 (6) | 0.0161 (6) | 0.0096 (5) | −0.0084 (5) | −0.0017 (5) |
O4 | 0.0320 (6) | 0.0366 (7) | 0.0183 (6) | 0.0179 (5) | −0.0118 (5) | −0.0038 (5) |
N5 | 0.0244 (6) | 0.0215 (6) | 0.0160 (6) | 0.0040 (5) | −0.0064 (5) | −0.0052 (5) |
C9 | 0.0199 (7) | 0.0149 (7) | 0.0165 (7) | −0.0031 (5) | −0.0071 (6) | 0.0010 (5) |
N6 | 0.0315 (7) | 0.0201 (6) | 0.0194 (7) | 0.0056 (5) | −0.0082 (5) | −0.0032 (5) |
O5 | 0.0326 (6) | 0.0313 (6) | 0.0168 (6) | 0.0131 (5) | −0.0051 (5) | −0.0001 (5) |
C2 | 0.0204 (7) | 0.0162 (7) | 0.0206 (8) | 0.0018 (6) | −0.0074 (6) | 0.0007 (6) |
C8 | 0.0225 (7) | 0.0174 (7) | 0.0162 (7) | 0.0001 (6) | −0.0077 (6) | 0.0007 (6) |
C47 | 0.0278 (8) | 0.0218 (7) | 0.0147 (7) | 0.0027 (6) | −0.0042 (6) | −0.0079 (6) |
C1 | 0.0185 (7) | 0.0134 (7) | 0.0178 (7) | −0.0020 (5) | −0.0033 (5) | −0.0009 (5) |
C10 | 0.0178 (7) | 0.0147 (7) | 0.0186 (7) | −0.0026 (5) | −0.0052 (6) | −0.0006 (6) |
C4 | 0.0234 (7) | 0.0197 (7) | 0.0193 (8) | 0.0015 (6) | −0.0024 (6) | −0.0033 (6) |
C7 | 0.0197 (7) | 0.0140 (7) | 0.0209 (8) | −0.0014 (5) | −0.0072 (6) | 0.0009 (6) |
O6 | 0.0361 (7) | 0.0364 (7) | 0.0217 (6) | 0.0189 (5) | −0.0030 (5) | −0.0012 (5) |
C11 | 0.0194 (7) | 0.0181 (7) | 0.0190 (8) | 0.0020 (6) | −0.0071 (6) | 0.0011 (6) |
C5 | 0.0206 (7) | 0.0143 (7) | 0.0241 (8) | −0.0002 (5) | −0.0066 (6) | 0.0000 (6) |
C14 | 0.0219 (7) | 0.0202 (7) | 0.0238 (8) | 0.0047 (6) | −0.0087 (6) | 0.0028 (6) |
C53 | 0.0280 (8) | 0.0199 (7) | 0.0172 (7) | 0.0055 (6) | −0.0076 (6) | −0.0055 (6) |
C52 | 0.0318 (8) | 0.0201 (7) | 0.0163 (8) | 0.0035 (6) | −0.0048 (6) | −0.0056 (6) |
C48 | 0.0284 (8) | 0.0321 (9) | 0.0223 (8) | 0.0014 (7) | −0.0061 (7) | −0.0097 (7) |
C3 | 0.0255 (7) | 0.0170 (7) | 0.0174 (7) | −0.0023 (6) | −0.0078 (6) | 0.0012 (6) |
C57 | 0.0307 (8) | 0.0220 (8) | 0.0214 (8) | 0.0024 (6) | −0.0068 (6) | −0.0016 (6) |
C58 | 0.0243 (7) | 0.0204 (7) | 0.0167 (7) | 0.0053 (6) | −0.0066 (6) | −0.0063 (6) |
C51 | 0.0443 (10) | 0.0221 (8) | 0.0223 (8) | 0.0010 (7) | −0.0039 (7) | −0.0021 (7) |
C13 | 0.0221 (7) | 0.0198 (7) | 0.0226 (8) | 0.0037 (6) | −0.0038 (6) | −0.0010 (6) |
C54 | 0.0283 (8) | 0.0296 (9) | 0.0306 (9) | 0.0072 (7) | −0.0139 (7) | −0.0061 (7) |
C12 | 0.0239 (7) | 0.0201 (7) | 0.0162 (7) | 0.0004 (6) | −0.0065 (6) | 0.0014 (6) |
C15 | 0.0212 (7) | 0.0193 (7) | 0.0180 (7) | −0.0009 (6) | −0.0067 (6) | 0.0011 (6) |
C56 | 0.0310 (9) | 0.0263 (8) | 0.0289 (9) | −0.0041 (7) | −0.0045 (7) | −0.0052 (7) |
C49 | 0.0308 (9) | 0.0398 (10) | 0.0278 (9) | −0.0080 (7) | −0.0009 (7) | −0.0122 (8) |
C50 | 0.0461 (10) | 0.0277 (9) | 0.0277 (9) | −0.0108 (8) | 0.0030 (8) | −0.0064 (7) |
C55 | 0.0237 (8) | 0.0359 (9) | 0.0384 (10) | 0.0004 (7) | −0.0099 (7) | −0.0099 (8) |
N7 | 0.0314 (7) | 0.0198 (6) | 0.0167 (6) | 0.0055 (5) | −0.0090 (5) | −0.0043 (5) |
C42 | 0.0303 (8) | 0.0192 (7) | 0.0169 (7) | 0.0057 (6) | −0.0084 (6) | −0.0067 (6) |
C41 | 0.0306 (8) | 0.0187 (7) | 0.0170 (7) | 0.0055 (6) | −0.0087 (6) | −0.0062 (6) |
C43 | 0.0303 (8) | 0.0281 (8) | 0.0223 (8) | 0.0058 (7) | −0.0102 (7) | −0.0063 (7) |
C46 | 0.0386 (9) | 0.0207 (8) | 0.0221 (8) | 0.0041 (7) | −0.0096 (7) | −0.0028 (6) |
C44 | 0.0309 (9) | 0.0329 (9) | 0.0275 (9) | −0.0002 (7) | −0.0054 (7) | −0.0094 (7) |
C45 | 0.0406 (10) | 0.0230 (8) | 0.0260 (9) | −0.0019 (7) | −0.0053 (7) | −0.0027 (7) |
N1 | 0.0277 (7) | 0.0199 (6) | 0.0246 (7) | −0.0005 (5) | −0.0081 (5) | −0.0048 (5) |
N2 | 0.0251 (7) | 0.0247 (7) | 0.0280 (7) | 0.0026 (5) | −0.0079 (6) | −0.0089 (6) |
C28 | 0.0233 (7) | 0.0195 (7) | 0.0202 (8) | 0.0005 (6) | −0.0042 (6) | −0.0073 (6) |
C40 | 0.0277 (8) | 0.0221 (8) | 0.0215 (8) | −0.0044 (6) | −0.0032 (6) | −0.0075 (6) |
C33 | 0.0255 (8) | 0.0197 (7) | 0.0204 (8) | 0.0007 (6) | −0.0052 (6) | −0.0064 (6) |
C32 | 0.0402 (9) | 0.0206 (8) | 0.0270 (9) | −0.0002 (7) | −0.0103 (7) | −0.0022 (7) |
C29 | 0.0239 (8) | 0.0291 (8) | 0.0311 (9) | −0.0002 (7) | −0.0077 (7) | −0.0083 (7) |
C34 | 0.0229 (8) | 0.0250 (8) | 0.0268 (8) | −0.0009 (6) | −0.0039 (6) | −0.0122 (7) |
C30 | 0.0281 (9) | 0.0366 (10) | 0.0373 (10) | −0.0125 (7) | −0.0027 (7) | −0.0119 (8) |
C35 | 0.0236 (8) | 0.0429 (10) | 0.0470 (11) | −0.0023 (7) | −0.0062 (8) | −0.0218 (9) |
C39 | 0.0476 (10) | 0.0266 (9) | 0.0262 (9) | −0.0112 (8) | −0.0035 (8) | −0.0054 (7) |
C31 | 0.0454 (10) | 0.0251 (9) | 0.0311 (9) | −0.0137 (8) | −0.0033 (8) | −0.0023 (7) |
C38 | 0.0512 (12) | 0.0364 (10) | 0.0347 (10) | −0.0244 (9) | 0.0065 (9) | −0.0133 (8) |
C36 | 0.0305 (9) | 0.0510 (12) | 0.0533 (13) | −0.0181 (9) | 0.0041 (9) | −0.0258 (10) |
N4 | 0.0270 (7) | 0.0216 (6) | 0.0197 (7) | 0.0039 (5) | −0.0049 (5) | −0.0036 (5) |
N3 | 0.0428 (8) | 0.0195 (7) | 0.0280 (8) | 0.0073 (6) | −0.0092 (6) | −0.0046 (6) |
C22 | 0.0317 (8) | 0.0197 (8) | 0.0214 (8) | 0.0030 (6) | −0.0011 (6) | −0.0061 (6) |
C16 | 0.0334 (9) | 0.0220 (8) | 0.0249 (8) | 0.0089 (7) | −0.0104 (7) | −0.0096 (7) |
C20 | 0.0327 (9) | 0.0227 (8) | 0.0230 (8) | 0.0039 (6) | −0.0056 (7) | −0.0064 (6) |
C21 | 0.0290 (8) | 0.0188 (7) | 0.0183 (8) | 0.0056 (6) | −0.0055 (6) | −0.0083 (6) |
C17 | 0.0362 (9) | 0.0314 (9) | 0.0381 (10) | 0.0122 (7) | −0.0175 (8) | −0.0121 (8) |
C18 | 0.0283 (9) | 0.0389 (10) | 0.0448 (11) | 0.0077 (8) | −0.0156 (8) | −0.0201 (9) |
C27 | 0.0391 (9) | 0.0204 (8) | 0.0244 (9) | 0.0048 (7) | −0.0045 (7) | −0.0065 (7) |
C26 | 0.0569 (12) | 0.0196 (8) | 0.0294 (10) | 0.0001 (8) | −0.0026 (8) | −0.0010 (7) |
C19 | 0.0333 (9) | 0.0276 (9) | 0.0342 (10) | −0.0028 (7) | −0.0041 (7) | −0.0147 (7) |
C24 | 0.0323 (9) | 0.0367 (10) | 0.0447 (11) | −0.0044 (8) | 0.0029 (8) | −0.0120 (9) |
C23 | 0.0304 (9) | 0.0305 (9) | 0.0345 (10) | 0.0024 (7) | −0.0028 (7) | −0.0043 (7) |
C25 | 0.0496 (11) | 0.0281 (9) | 0.0376 (11) | −0.0098 (8) | 0.0064 (9) | −0.0077 (8) |
O8 | 0.0926 (12) | 0.0853 (12) | 0.0239 (7) | 0.0692 (10) | −0.0118 (7) | −0.0086 (7) |
C73 | 0.0376 (10) | 0.0399 (11) | 0.0500 (12) | 0.0060 (8) | 0.0014 (9) | −0.0053 (9) |
O7—C1 | 1.3621 (17) | C41—C42i | 1.443 (2) |
O7—C9 | 1.3726 (16) | C43—C44 | 1.358 (2) |
O3—C7 | 1.2567 (16) | C43—H43 | 0.9500 |
C6—C1 | 1.3988 (19) | C46—C45 | 1.358 (2) |
C6—C5 | 1.419 (2) | C46—C41i | 1.425 (2) |
C6—C7 | 1.4360 (19) | C46—H46 | 0.9500 |
O2—C5 | 1.3531 (17) | C44—C45 | 1.424 (2) |
O2—H2O | 0.90 (2) | C44—H44 | 0.9500 |
O1—C3 | 1.3532 (17) | C45—H45 | 0.9500 |
O1—H1O | 0.89 (2) | N1—C28 | 1.3406 (18) |
O4—C8 | 1.3550 (17) | N1—C40 | 1.3436 (19) |
O4—H4O | 0.86 (2) | N2—C33 | 1.3423 (19) |
N5—C58 | 1.3366 (18) | N2—C34 | 1.347 (2) |
N5—C47 | 1.3464 (19) | C28—C29 | 1.427 (2) |
C9—C8 | 1.3615 (19) | C28—C33 | 1.437 (2) |
C9—C10 | 1.462 (2) | C40—C39 | 1.429 (2) |
N6—C53 | 1.3406 (19) | C40—C34 | 1.432 (2) |
N6—C52 | 1.3450 (19) | C33—C32 | 1.426 (2) |
O5—C12 | 1.3718 (17) | C32—C31 | 1.354 (2) |
O5—H5O | 0.92 (2) | C32—H32 | 0.9500 |
C2—C1 | 1.3878 (19) | C29—C30 | 1.358 (2) |
C2—C3 | 1.390 (2) | C29—H29 | 0.9500 |
C2—H2 | 0.9500 | C34—C35 | 1.428 (2) |
C8—C7 | 1.444 (2) | C30—C31 | 1.421 (2) |
C47—C48 | 1.420 (2) | C30—H30 | 0.9500 |
C47—C52 | 1.434 (2) | C35—C36 | 1.356 (3) |
C10—C15 | 1.4048 (18) | C35—H35 | 0.9500 |
C10—C11 | 1.4054 (19) | C39—C38 | 1.358 (2) |
C4—C5 | 1.375 (2) | C39—H39 | 0.9500 |
C4—C3 | 1.402 (2) | C31—H31 | 0.9500 |
C4—H4 | 0.9500 | C38—C36 | 1.412 (3) |
O6—C13 | 1.3560 (18) | C38—H38 | 0.9500 |
O6—H6O | 0.89 (2) | C36—H36 | 0.9500 |
C11—C12 | 1.377 (2) | N4—C21 | 1.3450 (19) |
C11—H11 | 0.9500 | N4—C22 | 1.3489 (19) |
C14—C15 | 1.382 (2) | N3—C27 | 1.340 (2) |
C14—C13 | 1.387 (2) | N3—C16 | 1.341 (2) |
C14—H14 | 0.9500 | C22—C23 | 1.421 (2) |
C53—C54 | 1.424 (2) | C22—C27 | 1.429 (2) |
C53—C58 | 1.4392 (19) | C16—C17 | 1.420 (2) |
C52—C51 | 1.424 (2) | C16—C21 | 1.442 (2) |
C48—C49 | 1.362 (2) | C20—C19 | 1.362 (2) |
C48—H48 | 0.9500 | C20—C21 | 1.421 (2) |
C57—C56 | 1.357 (2) | C20—H20 | 0.9500 |
C57—C58 | 1.421 (2) | C17—C18 | 1.353 (2) |
C57—H57 | 0.9500 | C17—H17 | 0.9500 |
C51—C50 | 1.357 (2) | C18—C19 | 1.427 (2) |
C51—H51 | 0.9500 | C18—H18 | 0.9500 |
C13—C12 | 1.4028 (19) | C27—C26 | 1.427 (2) |
C54—C55 | 1.357 (2) | C26—C25 | 1.353 (3) |
C54—H54 | 0.9500 | C26—H26 | 0.9500 |
C15—H15 | 0.9500 | C19—H19 | 0.9500 |
C56—C55 | 1.424 (2) | C24—C23 | 1.361 (2) |
C56—H56 | 0.9500 | C24—C25 | 1.414 (3) |
C49—C50 | 1.419 (2) | C24—H24 | 0.9500 |
C49—H49 | 0.9500 | C23—H23 | 0.9500 |
C50—H50 | 0.9500 | C25—H25 | 0.9500 |
C55—H55 | 0.9500 | O8—C73 | 1.384 (2) |
N7—C41 | 1.3430 (19) | O8—H8O | 0.85 (2) |
N7—C42 | 1.3492 (19) | C73—H73A | 0.9800 |
C42—C43 | 1.422 (2) | C73—H73B | 0.9800 |
C42—C41i | 1.443 (2) | C73—H73C | 0.9800 |
C41—C46i | 1.425 (2) | ||
C1—O7—C9 | 121.09 (11) | C44—C43—C42 | 120.31 (14) |
C1—C6—C5 | 117.79 (12) | C44—C43—H43 | 119.8 |
C1—C6—C7 | 120.00 (13) | C42—C43—H43 | 119.8 |
C5—C6—C7 | 122.19 (12) | C45—C46—C41i | 120.59 (14) |
C5—O2—H2O | 105.7 (14) | C45—C46—H46 | 119.7 |
C3—O1—H1O | 109.2 (13) | C41i—C46—H46 | 119.7 |
C8—O4—H4O | 113.0 (14) | C43—C44—C45 | 120.80 (15) |
C58—N5—C47 | 117.82 (12) | C43—C44—H44 | 119.6 |
C8—C9—O7 | 120.38 (13) | C45—C44—H44 | 119.6 |
C8—C9—C10 | 127.83 (13) | C46—C45—C44 | 120.72 (15) |
O7—C9—C10 | 111.78 (11) | C46—C45—H45 | 119.6 |
C53—N6—C52 | 117.54 (12) | C44—C45—H45 | 119.6 |
C12—O5—H5O | 109.1 (13) | C28—N1—C40 | 116.78 (13) |
C1—C2—C3 | 117.33 (13) | C33—N2—C34 | 116.51 (13) |
C1—C2—H2 | 121.3 | N1—C28—C29 | 119.47 (13) |
C3—C2—H2 | 121.3 | N1—C28—C33 | 121.70 (13) |
O4—C8—C9 | 120.10 (13) | C29—C28—C33 | 118.83 (13) |
O4—C8—C7 | 118.03 (12) | N1—C40—C39 | 119.40 (14) |
C9—C8—C7 | 121.82 (13) | N1—C40—C34 | 121.56 (13) |
N5—C47—C48 | 119.32 (13) | C39—C40—C34 | 119.03 (14) |
N5—C47—C52 | 121.06 (13) | N2—C33—C32 | 119.39 (14) |
C48—C47—C52 | 119.61 (14) | N2—C33—C28 | 121.63 (13) |
O7—C1—C2 | 116.15 (12) | C32—C33—C28 | 118.98 (13) |
O7—C1—C6 | 120.90 (12) | C31—C32—C33 | 120.12 (15) |
C2—C1—C6 | 122.95 (14) | C31—C32—H32 | 119.9 |
C15—C10—C11 | 118.14 (13) | C33—C32—H32 | 119.9 |
C15—C10—C9 | 120.56 (13) | C30—C29—C28 | 120.15 (15) |
C11—C10—C9 | 121.29 (12) | C30—C29—H29 | 119.9 |
C5—C4—C3 | 119.73 (14) | C28—C29—H29 | 119.9 |
C5—C4—H4 | 120.1 | N2—C34—C35 | 119.40 (15) |
C3—C4—H4 | 120.1 | N2—C34—C40 | 121.80 (13) |
O3—C7—C6 | 123.46 (14) | C35—C34—C40 | 118.79 (15) |
O3—C7—C8 | 120.74 (13) | C29—C30—C31 | 120.84 (15) |
C6—C7—C8 | 115.78 (12) | C29—C30—H30 | 119.6 |
C13—O6—H6O | 113.6 (15) | C31—C30—H30 | 119.6 |
C12—C11—C10 | 120.98 (13) | C36—C35—C34 | 120.07 (17) |
C12—C11—H11 | 119.5 | C36—C35—H35 | 120.0 |
C10—C11—H11 | 119.5 | C34—C35—H35 | 120.0 |
O2—C5—C4 | 119.58 (14) | C38—C39—C40 | 119.95 (17) |
O2—C5—C6 | 120.06 (13) | C38—C39—H39 | 120.0 |
C4—C5—C6 | 120.36 (13) | C40—C39—H39 | 120.0 |
C15—C14—C13 | 121.09 (13) | C32—C31—C30 | 121.07 (15) |
C15—C14—H14 | 119.5 | C32—C31—H31 | 119.5 |
C13—C14—H14 | 119.5 | C30—C31—H31 | 119.5 |
N6—C53—C54 | 120.09 (13) | C39—C38—C36 | 120.96 (16) |
N6—C53—C58 | 121.29 (13) | C39—C38—H38 | 119.5 |
C54—C53—C58 | 118.61 (14) | C36—C38—H38 | 119.5 |
N6—C52—C51 | 120.11 (14) | C35—C36—C38 | 121.18 (16) |
N6—C52—C47 | 121.18 (13) | C35—C36—H36 | 119.4 |
C51—C52—C47 | 118.71 (14) | C38—C36—H36 | 119.4 |
C49—C48—C47 | 119.69 (15) | C21—N4—C22 | 117.59 (12) |
C49—C48—H48 | 120.2 | C27—N3—C16 | 116.80 (13) |
C47—C48—H48 | 120.2 | N4—C22—C23 | 119.96 (14) |
O1—C3—C2 | 121.93 (13) | N4—C22—C27 | 120.91 (14) |
O1—C3—C4 | 116.25 (13) | C23—C22—C27 | 119.12 (14) |
C2—C3—C4 | 121.82 (13) | N3—C16—C17 | 119.64 (14) |
C56—C57—C58 | 120.06 (14) | N3—C16—C21 | 121.86 (14) |
C56—C57—H57 | 120.0 | C17—C16—C21 | 118.48 (15) |
C58—C57—H57 | 120.0 | C19—C20—C21 | 119.83 (15) |
N5—C58—C57 | 119.63 (13) | C19—C20—H20 | 120.1 |
N5—C58—C53 | 121.04 (13) | C21—C20—H20 | 120.1 |
C57—C58—C53 | 119.33 (13) | N4—C21—C20 | 119.79 (13) |
C50—C51—C52 | 119.95 (15) | N4—C21—C16 | 120.63 (14) |
C50—C51—H51 | 120.0 | C20—C21—C16 | 119.57 (14) |
C52—C51—H51 | 120.0 | C18—C17—C16 | 120.34 (15) |
O6—C13—C14 | 118.92 (13) | C18—C17—H17 | 119.8 |
O6—C13—C12 | 122.24 (13) | C16—C17—H17 | 119.8 |
C14—C13—C12 | 118.84 (14) | C17—C18—C19 | 121.23 (15) |
C55—C54—C53 | 120.20 (14) | C17—C18—H18 | 119.4 |
C55—C54—H54 | 119.9 | C19—C18—H18 | 119.4 |
C53—C54—H54 | 119.9 | N3—C27—C26 | 119.42 (15) |
O5—C12—C11 | 122.44 (12) | N3—C27—C22 | 122.13 (15) |
O5—C12—C13 | 117.12 (13) | C26—C27—C22 | 118.44 (16) |
C11—C12—C13 | 120.42 (13) | C25—C26—C27 | 120.65 (16) |
C14—C15—C10 | 120.51 (13) | C25—C26—H26 | 119.7 |
C14—C15—H15 | 119.7 | C27—C26—H26 | 119.7 |
C10—C15—H15 | 119.7 | C20—C19—C18 | 120.54 (16) |
C57—C56—C55 | 120.79 (15) | C20—C19—H19 | 119.7 |
C57—C56—H56 | 119.6 | C18—C19—H19 | 119.7 |
C55—C56—H56 | 119.6 | C23—C24—C25 | 120.69 (17) |
C48—C49—C50 | 120.75 (16) | C23—C24—H24 | 119.7 |
C48—C49—H49 | 119.6 | C25—C24—H24 | 119.7 |
C50—C49—H49 | 119.6 | C24—C23—C22 | 120.26 (16) |
C51—C50—C49 | 121.24 (15) | C24—C23—H23 | 119.9 |
C51—C50—H50 | 119.4 | C22—C23—H23 | 119.9 |
C49—C50—H50 | 119.4 | C26—C25—C24 | 120.78 (16) |
C54—C55—C56 | 120.99 (15) | C26—C25—H25 | 119.6 |
C54—C55—H55 | 119.5 | C24—C25—H25 | 119.6 |
C56—C55—H55 | 119.5 | C73—O8—H8O | 113.3 (16) |
C41—N7—C42 | 117.52 (12) | O8—C73—H73A | 109.5 |
N7—C42—C43 | 119.87 (13) | O8—C73—H73B | 109.5 |
N7—C42—C41i | 121.05 (14) | H73A—C73—H73B | 109.5 |
C43—C42—C41i | 119.08 (14) | O8—C73—H73C | 109.5 |
N7—C41—C46i | 120.11 (13) | H73A—C73—H73C | 109.5 |
N7—C41—C42i | 121.42 (14) | H73B—C73—H73C | 109.5 |
C46i—C41—C42i | 118.47 (14) |
Symmetry code: (i) −x, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4 | 0.95 | 2.11 | 2.7761 (18) | 126 |
C14—H14···N1 | 0.95 | 2.54 | 3.4641 (18) | 165 |
C20—H20···O3ii | 0.95 | 2.46 | 3.3386 (18) | 154 |
C17—H17···O6 | 0.95 | 2.63 | 3.463 (2) | 147 |
O5—H5O···N7 | 0.92 (2) | 1.99 (2) | 2.9068 (16) | 173.9 (18) |
O4—H4O···N5 | 0.86 (2) | 1.91 (2) | 2.6998 (15) | 152 (2) |
O6—H6O···O8 | 0.89 (2) | 1.76 (2) | 2.6123 (18) | 160 (2) |
O2—H2O···O3 | 0.90 (2) | 1.80 (2) | 2.6281 (15) | 152 (2) |
O1—H1O···N4iii | 0.89 (2) | 1.90 (2) | 2.7694 (16) | 164.6 (19) |
O8—H8O···N6i | 0.85 (2) | 1.96 (2) | 2.8113 (18) | 177 (2) |
Symmetry codes: (i) −x, −y+2, −z; (ii) x+1, y−1, z; (iii) −x+1, −y+1, −z+1. |
C33H22N3O8 | V = 1312.94 (18) Å3 |
Mr = 588.53 | Z = 2 |
Triclinic, P1 | F(000) = 610 |
a = 9.4800 (7) Å | Dx = 1.489 Mg m−3 |
b = 11.2614 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 13.5129 (10) Å | µ = 0.11 mm−1 |
α = 104.785 (4)° | T = 296 K |
β = 108.855 (4)° | Plate, red |
γ = 90.687 (4)° | 0.25 × 0.20 × 0.20 mm |
Absorption correction: analytical Bruker, AXS, 2008 | Rint = 0.042 |
Tmin = 0.974, Tmax = 0.979 | θmax = 26.0°, θmin = 1.7° |
14918 measured reflections | h = −11→11 |
5100 independent reflections | k = −13→13 |
3747 reflections with I > 2σ(I) | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0602P)2 + 0.3828P] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
5100 reflections | Δρmax = 0.45 e Å−3 |
417 parameters | Δρmin = −0.33 e Å−3 |
C33H22N3O8 | γ = 90.687 (4)° |
Mr = 588.53 | V = 1312.94 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.4800 (7) Å | Mo Kα radiation |
b = 11.2614 (9) Å | µ = 0.11 mm−1 |
c = 13.5129 (10) Å | T = 296 K |
α = 104.785 (4)° | 0.25 × 0.20 × 0.20 mm |
β = 108.855 (4)° |
Absorption correction: analytical Bruker, AXS, 2008 | 5100 independent reflections |
Tmin = 0.974, Tmax = 0.979 | 3747 reflections with I > 2σ(I) |
14918 measured reflections | Rint = 0.042 |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.45 e Å−3 |
5100 reflections | Δρmin = −0.33 e Å−3 |
417 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C6 | 1.12658 (18) | 0.61921 (16) | 0.48970 (13) | 0.0177 (4) | |
C9 | 1.01319 (19) | 0.83645 (16) | 0.56939 (13) | 0.0181 (4) | |
C10 | 0.93537 (19) | 0.94619 (16) | 0.59240 (13) | 0.0185 (4) | |
C2 | 0.89885 (19) | 0.57290 (16) | 0.33188 (14) | 0.0214 (4) | |
H2 | 0.8070 | 0.5950 | 0.2938 | 0.026* | |
C7 | 1.21259 (19) | 0.70128 (16) | 0.59202 (14) | 0.0196 (4) | |
C11 | 0.99584 (19) | 1.04189 (16) | 0.68797 (14) | 0.0196 (4) | |
H11 | 1.0879 | 1.0357 | 0.7378 | 0.024* | |
C4 | 1.08883 (19) | 0.42917 (16) | 0.34736 (14) | 0.0205 (4) | |
H4 | 1.1216 | 0.3549 | 0.3187 | 0.025* | |
C1 | 0.98810 (18) | 0.64865 (15) | 0.43089 (13) | 0.0175 (4) | |
C32 | 0.6338 (2) | 0.48932 (16) | −0.01607 (14) | 0.0227 (4) | |
C8 | 1.14629 (19) | 0.80879 (16) | 0.63174 (13) | 0.0194 (4) | |
C22 | 1.24935 (19) | 0.16223 (16) | 0.03853 (14) | 0.0220 (4) | |
C12 | 0.92299 (19) | 1.14465 (16) | 0.71025 (14) | 0.0201 (4) | |
C33 | 0.4927 (2) | 0.47876 (16) | 0.09240 (14) | 0.0222 (4) | |
C21 | 1.3834 (2) | 0.18053 (16) | −0.07152 (14) | 0.0225 (4) | |
C14 | 0.7239 (2) | 1.06147 (17) | 0.54122 (14) | 0.0238 (4) | |
H14 | 0.6319 | 1.0680 | 0.4916 | 0.029* | |
C16 | 1.5176 (2) | 0.16347 (16) | 0.00829 (14) | 0.0219 (4) | |
C27 | 1.38315 (19) | 0.14434 (16) | 0.11809 (14) | 0.0206 (4) | |
C17 | 1.6548 (2) | 0.16442 (17) | −0.01300 (16) | 0.0287 (4) | |
H17 | 1.7428 | 0.1538 | 0.0385 | 0.034* | |
C3 | 0.9506 (2) | 0.46257 (16) | 0.29093 (14) | 0.0212 (4) | |
C26 | 1.3738 (2) | 0.12335 (17) | 0.21515 (15) | 0.0263 (4) | |
H26 | 1.4598 | 0.1116 | 0.2678 | 0.032* | |
C31 | 0.7700 (2) | 0.47732 (18) | −0.03871 (16) | 0.0299 (5) | |
H31 | 0.8538 | 0.4575 | 0.0108 | 0.036* | |
C5 | 1.17556 (19) | 0.50616 (16) | 0.44483 (14) | 0.0200 (4) | |
C28 | 0.5210 (2) | 0.54122 (18) | −0.18832 (15) | 0.0286 (4) | |
H28 | 0.4400 | 0.5639 | −0.2380 | 0.034* | |
C13 | 0.7853 (2) | 1.15602 (16) | 0.63573 (14) | 0.0205 (4) | |
C23 | 1.1118 (2) | 0.15935 (18) | 0.05933 (16) | 0.0303 (5) | |
H23 | 1.0240 | 0.1717 | 0.0085 | 0.036* | |
C20 | 1.3921 (2) | 0.19844 (18) | −0.17006 (16) | 0.0308 (5) | |
H20 | 1.3061 | 0.2106 | −0.2226 | 0.037* | |
C19 | 1.5248 (2) | 0.19782 (19) | −0.18770 (17) | 0.0344 (5) | |
H19 | 1.5290 | 0.2086 | −0.2527 | 0.041* | |
C15 | 0.7968 (2) | 0.95755 (17) | 0.51923 (14) | 0.0221 (4) | |
H15 | 0.7533 | 0.8949 | 0.4554 | 0.027* | |
C24 | 1.1082 (2) | 0.13861 (19) | 0.15303 (16) | 0.0323 (5) | |
H24 | 1.0177 | 0.1363 | 0.1659 | 0.039* | |
C25 | 1.2410 (2) | 0.12041 (18) | 0.23148 (15) | 0.0305 (5) | |
H25 | 1.2365 | 0.1062 | 0.2953 | 0.037* | |
C18 | 1.6576 (2) | 0.18084 (18) | −0.10807 (17) | 0.0333 (5) | |
H18 | 1.7478 | 0.1810 | −0.1215 | 0.040* | |
C29 | 0.6520 (2) | 0.52737 (19) | −0.20756 (16) | 0.0323 (5) | |
H29 | 0.6595 | 0.5395 | −0.2713 | 0.039* | |
C30 | 0.7781 (2) | 0.4947 (2) | −0.13254 (17) | 0.0344 (5) | |
H30 | 0.8669 | 0.4852 | −0.1477 | 0.041* | |
N5 | 0.62433 (16) | 0.46832 (14) | 0.07534 (11) | 0.0231 (3) | |
N11 | 1.51600 (16) | 0.14627 (13) | 0.10304 (12) | 0.0222 (3) | |
N12 | 1.25137 (16) | 0.18162 (14) | −0.05501 (12) | 0.0233 (3) | |
O7 | 0.93564 (12) | 0.75612 (11) | 0.47017 (9) | 0.0196 (3) | |
O3 | 1.34208 (13) | 0.68253 (12) | 0.64651 (10) | 0.0263 (3) | |
O1 | 0.87145 (15) | 0.38163 (12) | 0.19564 (10) | 0.0301 (3) | |
O4 | 1.22341 (15) | 0.88546 (12) | 0.73073 (11) | 0.0297 (3) | |
O8 | 0.47995 (18) | 1.27143 (15) | 0.48651 (13) | 0.0503 (4) | |
O2 | 1.30965 (14) | 0.47435 (13) | 0.50006 (11) | 0.0293 (3) | |
O6 | 0.71816 (15) | 1.26000 (12) | 0.66039 (11) | 0.0273 (3) | |
O5 | 0.97912 (15) | 1.23836 (12) | 0.80397 (11) | 0.0289 (3) | |
H1O | 0.784 (3) | 0.415 (2) | 0.1621 (19) | 0.053 (7)* | |
H5O | 1.074 (3) | 1.224 (2) | 0.847 (2) | 0.067 (8)* | |
H4O | 1.297 (3) | 0.853 (2) | 0.765 (2) | 0.057 (8)* | |
H2O | 1.345 (3) | 0.537 (2) | 0.5569 (19) | 0.048 (7)* | |
H6O | 0.640 (3) | 1.258 (3) | 0.601 (2) | 0.075 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C6 | 0.0179 (9) | 0.0176 (9) | 0.0191 (9) | 0.0025 (7) | 0.0069 (7) | 0.0066 (7) |
C9 | 0.0197 (9) | 0.0182 (9) | 0.0176 (9) | 0.0011 (7) | 0.0071 (7) | 0.0061 (7) |
C10 | 0.0202 (9) | 0.0186 (9) | 0.0203 (9) | 0.0040 (7) | 0.0087 (7) | 0.0091 (7) |
C2 | 0.0192 (9) | 0.0231 (10) | 0.0204 (9) | 0.0062 (7) | 0.0038 (7) | 0.0072 (8) |
C7 | 0.0203 (9) | 0.0191 (9) | 0.0209 (9) | 0.0024 (7) | 0.0065 (7) | 0.0084 (7) |
C11 | 0.0185 (9) | 0.0197 (9) | 0.0215 (9) | 0.0048 (7) | 0.0058 (7) | 0.0083 (7) |
C4 | 0.0231 (9) | 0.0168 (9) | 0.0234 (9) | 0.0067 (7) | 0.0105 (8) | 0.0049 (7) |
C1 | 0.0201 (9) | 0.0154 (9) | 0.0208 (9) | 0.0052 (7) | 0.0097 (7) | 0.0077 (7) |
C32 | 0.0241 (10) | 0.0156 (9) | 0.0225 (9) | 0.0035 (7) | 0.0040 (8) | 0.0003 (7) |
C8 | 0.0202 (9) | 0.0173 (9) | 0.0180 (9) | 0.0007 (7) | 0.0041 (7) | 0.0031 (7) |
C22 | 0.0220 (9) | 0.0181 (9) | 0.0218 (9) | 0.0010 (7) | 0.0060 (7) | 0.0001 (7) |
C12 | 0.0233 (9) | 0.0191 (9) | 0.0200 (9) | 0.0026 (7) | 0.0090 (7) | 0.0067 (7) |
C33 | 0.0246 (10) | 0.0153 (9) | 0.0215 (9) | 0.0042 (7) | 0.0037 (8) | 0.0011 (7) |
C21 | 0.0237 (9) | 0.0159 (9) | 0.0243 (10) | −0.0003 (7) | 0.0072 (8) | 0.0008 (7) |
C14 | 0.0235 (9) | 0.0268 (10) | 0.0219 (9) | 0.0093 (8) | 0.0063 (8) | 0.0095 (8) |
C16 | 0.0220 (9) | 0.0127 (9) | 0.0265 (10) | 0.0010 (7) | 0.0067 (8) | −0.0008 (7) |
C27 | 0.0223 (9) | 0.0134 (9) | 0.0214 (9) | 0.0001 (7) | 0.0054 (7) | −0.0008 (7) |
C17 | 0.0246 (10) | 0.0210 (10) | 0.0353 (11) | 0.0022 (8) | 0.0097 (8) | −0.0006 (8) |
C3 | 0.0234 (9) | 0.0208 (10) | 0.0184 (9) | 0.0023 (7) | 0.0069 (7) | 0.0039 (7) |
C26 | 0.0272 (10) | 0.0229 (10) | 0.0243 (10) | −0.0001 (8) | 0.0032 (8) | 0.0056 (8) |
C31 | 0.0209 (10) | 0.0316 (11) | 0.0304 (11) | 0.0048 (8) | 0.0035 (8) | 0.0035 (9) |
C5 | 0.0180 (9) | 0.0221 (10) | 0.0227 (9) | 0.0067 (7) | 0.0073 (7) | 0.0105 (8) |
C28 | 0.0311 (11) | 0.0269 (11) | 0.0244 (10) | 0.0064 (8) | 0.0046 (8) | 0.0071 (8) |
C13 | 0.0244 (9) | 0.0179 (9) | 0.0251 (10) | 0.0079 (7) | 0.0133 (8) | 0.0092 (8) |
C23 | 0.0227 (10) | 0.0342 (12) | 0.0304 (11) | 0.0022 (8) | 0.0075 (8) | 0.0047 (9) |
C20 | 0.0336 (11) | 0.0284 (11) | 0.0273 (11) | −0.0001 (9) | 0.0075 (9) | 0.0055 (9) |
C19 | 0.0450 (13) | 0.0291 (11) | 0.0320 (11) | −0.0044 (9) | 0.0197 (10) | 0.0048 (9) |
C15 | 0.0251 (10) | 0.0199 (10) | 0.0202 (9) | 0.0048 (8) | 0.0066 (8) | 0.0047 (8) |
C24 | 0.0273 (10) | 0.0337 (12) | 0.0350 (11) | −0.0020 (9) | 0.0161 (9) | 0.0007 (9) |
C25 | 0.0378 (11) | 0.0276 (11) | 0.0241 (10) | −0.0049 (9) | 0.0123 (9) | 0.0016 (8) |
C18 | 0.0323 (11) | 0.0255 (11) | 0.0444 (13) | 0.0002 (9) | 0.0237 (10) | 0.0000 (9) |
C29 | 0.0393 (12) | 0.0305 (12) | 0.0293 (11) | 0.0024 (9) | 0.0146 (9) | 0.0080 (9) |
C30 | 0.0278 (11) | 0.0380 (12) | 0.0374 (12) | 0.0029 (9) | 0.0142 (9) | 0.0061 (10) |
N5 | 0.0231 (8) | 0.0204 (8) | 0.0197 (8) | 0.0054 (6) | 0.0019 (6) | 0.0018 (6) |
N11 | 0.0224 (8) | 0.0151 (8) | 0.0249 (8) | 0.0023 (6) | 0.0060 (6) | 0.0004 (6) |
N12 | 0.0219 (8) | 0.0212 (8) | 0.0224 (8) | 0.0017 (6) | 0.0043 (6) | 0.0024 (6) |
O7 | 0.0196 (6) | 0.0164 (6) | 0.0193 (6) | 0.0055 (5) | 0.0035 (5) | 0.0030 (5) |
O3 | 0.0195 (6) | 0.0249 (7) | 0.0271 (7) | 0.0076 (5) | −0.0002 (5) | 0.0045 (6) |
O1 | 0.0282 (7) | 0.0266 (8) | 0.0229 (7) | 0.0088 (6) | −0.0010 (6) | −0.0028 (6) |
O4 | 0.0269 (7) | 0.0230 (7) | 0.0257 (7) | 0.0109 (6) | −0.0035 (6) | −0.0012 (6) |
O8 | 0.0505 (10) | 0.0434 (10) | 0.0492 (10) | 0.0144 (8) | 0.0065 (8) | 0.0122 (8) |
O2 | 0.0225 (7) | 0.0255 (8) | 0.0304 (8) | 0.0106 (6) | 0.0005 (6) | 0.0016 (6) |
O6 | 0.0313 (8) | 0.0239 (7) | 0.0273 (7) | 0.0140 (6) | 0.0098 (6) | 0.0076 (6) |
O5 | 0.0298 (7) | 0.0224 (7) | 0.0263 (7) | 0.0084 (6) | 0.0041 (6) | −0.0008 (6) |
C6—C1 | 1.391 (2) | C14—H14 | 0.9300 |
C6—C5 | 1.416 (2) | C16—N11 | 1.348 (2) |
C6—C7 | 1.425 (2) | C16—C17 | 1.420 (3) |
C9—C8 | 1.362 (2) | C27—N11 | 1.340 (2) |
C9—O7 | 1.373 (2) | C27—C26 | 1.420 (2) |
C9—C10 | 1.464 (2) | C17—C18 | 1.352 (3) |
C10—C15 | 1.396 (2) | C17—H17 | 0.9300 |
C10—C11 | 1.398 (2) | C3—O1 | 1.346 (2) |
C2—C1 | 1.379 (2) | C26—C25 | 1.348 (3) |
C2—C3 | 1.389 (2) | C26—H26 | 0.9300 |
C2—H2 | 0.9300 | C31—C30 | 1.357 (3) |
C7—O3 | 1.263 (2) | C31—H31 | 0.9300 |
C7—C8 | 1.433 (2) | C5—O2 | 1.355 (2) |
C11—C12 | 1.372 (2) | C28—C29 | 1.351 (3) |
C11—H11 | 0.9300 | C28—C33i | 1.416 (3) |
C4—C5 | 1.365 (2) | C28—H28 | 0.9300 |
C4—C3 | 1.397 (2) | C13—O6 | 1.358 (2) |
C4—H4 | 0.9300 | C23—C24 | 1.355 (3) |
C1—O7 | 1.361 (2) | C23—H23 | 0.9300 |
C32—N5 | 1.345 (2) | C20—C19 | 1.354 (3) |
C32—C31 | 1.420 (3) | C20—H20 | 0.9300 |
C32—C33i | 1.425 (2) | C19—C18 | 1.419 (3) |
C8—O4 | 1.354 (2) | C19—H19 | 0.9300 |
C22—N12 | 1.342 (2) | C15—H15 | 0.9300 |
C22—C23 | 1.422 (3) | C24—C25 | 1.416 (3) |
C22—C27 | 1.429 (2) | C24—H24 | 0.9300 |
C12—O5 | 1.367 (2) | C25—H25 | 0.9300 |
C12—C13 | 1.398 (2) | C18—H18 | 0.9300 |
C33—N5 | 1.342 (2) | C29—C30 | 1.418 (3) |
C33—C28i | 1.416 (3) | C29—H29 | 0.9300 |
C33—C32i | 1.425 (2) | C30—H30 | 0.9300 |
C21—N12 | 1.340 (2) | O1—H1O | 0.94 (3) |
C21—C20 | 1.424 (3) | O4—H4O | 0.85 (3) |
C21—C16 | 1.429 (2) | O2—H2O | 0.86 (2) |
C14—C15 | 1.382 (2) | O6—H6O | 0.89 (3) |
C14—C13 | 1.384 (2) | O5—H5O | 0.95 (3) |
C1—C6—C5 | 117.72 (15) | O1—C3—C2 | 122.48 (16) |
C1—C6—C7 | 119.79 (15) | O1—C3—C4 | 116.10 (16) |
C5—C6—C7 | 122.49 (15) | C2—C3—C4 | 121.42 (16) |
C8—C9—O7 | 119.82 (15) | C25—C26—C27 | 120.44 (18) |
C8—C9—C10 | 128.55 (16) | C25—C26—H26 | 119.8 |
O7—C9—C10 | 111.63 (14) | C27—C26—H26 | 119.8 |
C15—C10—C11 | 117.96 (16) | C30—C31—C32 | 120.07 (18) |
C15—C10—C9 | 120.54 (15) | C30—C31—H31 | 120.0 |
C11—C10—C9 | 121.50 (15) | C32—C31—H31 | 120.0 |
C1—C2—C3 | 117.80 (16) | O2—C5—C4 | 119.97 (16) |
C1—C2—H2 | 121.1 | O2—C5—C6 | 119.31 (15) |
C3—C2—H2 | 121.1 | C4—C5—C6 | 120.71 (15) |
O3—C7—C6 | 122.63 (16) | C29—C28—C33i | 119.92 (18) |
O3—C7—C8 | 120.30 (15) | C29—C28—H28 | 120.0 |
C6—C7—C8 | 117.06 (15) | C33i—C28—H28 | 120.0 |
C12—C11—C10 | 121.75 (16) | O6—C13—C14 | 123.23 (16) |
C12—C11—H11 | 119.1 | O6—C13—C12 | 117.90 (16) |
C10—C11—H11 | 119.1 | C14—C13—C12 | 118.87 (16) |
C5—C4—C3 | 119.64 (16) | C24—C23—C22 | 120.14 (18) |
C5—C4—H4 | 120.2 | C24—C23—H23 | 119.9 |
C3—C4—H4 | 120.2 | C22—C23—H23 | 119.9 |
O7—C1—C2 | 117.13 (15) | C19—C20—C21 | 120.33 (19) |
O7—C1—C6 | 120.17 (15) | C19—C20—H20 | 119.8 |
C2—C1—C6 | 122.70 (16) | C21—C20—H20 | 119.8 |
N5—C32—C31 | 120.12 (16) | C20—C19—C18 | 120.71 (18) |
N5—C32—C33i | 120.75 (16) | C20—C19—H19 | 119.6 |
C31—C32—C33i | 119.11 (17) | C18—C19—H19 | 119.6 |
O4—C8—C9 | 120.88 (16) | C14—C15—C10 | 120.32 (17) |
O4—C8—C7 | 118.08 (15) | C14—C15—H15 | 119.8 |
C9—C8—C7 | 120.96 (15) | C10—C15—H15 | 119.8 |
N12—C22—C23 | 119.66 (16) | C23—C24—C25 | 120.61 (18) |
N12—C22—C27 | 121.27 (16) | C23—C24—H24 | 119.7 |
C23—C22—C27 | 119.07 (16) | C25—C24—H24 | 119.7 |
O5—C12—C11 | 122.65 (16) | C26—C25—C24 | 121.05 (18) |
O5—C12—C13 | 117.47 (16) | C26—C25—H25 | 119.5 |
C11—C12—C13 | 119.87 (16) | C24—C25—H25 | 119.5 |
N5—C33—C28i | 119.59 (16) | C17—C18—C19 | 120.97 (18) |
N5—C33—C32i | 121.24 (16) | C17—C18—H18 | 119.5 |
C28i—C33—C32i | 119.17 (17) | C19—C18—H18 | 119.5 |
N12—C21—C20 | 119.72 (17) | C28—C29—C30 | 121.32 (18) |
N12—C21—C16 | 121.65 (16) | C28—C29—H29 | 119.3 |
C20—C21—C16 | 118.63 (17) | C30—C29—H29 | 119.3 |
C15—C14—C13 | 121.22 (16) | C31—C30—C29 | 120.39 (18) |
C15—C14—H14 | 119.4 | C31—C30—H30 | 119.8 |
C13—C14—H14 | 119.4 | C29—C30—H30 | 119.8 |
N11—C16—C17 | 119.58 (17) | C33—N5—C32 | 118.01 (15) |
N11—C16—C21 | 121.14 (16) | C27—N11—C16 | 117.03 (15) |
C17—C16—C21 | 119.28 (17) | C21—N12—C22 | 117.16 (15) |
N11—C27—C26 | 119.59 (16) | C1—O7—C9 | 121.95 (13) |
N11—C27—C22 | 121.72 (16) | C3—O1—H1O | 109.5 (14) |
C26—C27—C22 | 118.69 (16) | C8—O4—H4O | 111.9 (17) |
C18—C17—C16 | 120.08 (18) | C5—O2—H2O | 104.0 (16) |
C18—C17—H17 | 120.0 | C13—O6—H6O | 106.4 (18) |
C16—C17—H17 | 120.0 | C12—O5—H5O | 111.0 (16) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4 | 0.93 | 2.14 | 2.810 (2) | 128 |
C28—H28···O3ii | 0.93 | 2.29 | 3.134 (2) | 151 |
O1—H1O···N5 | 0.94 (3) | 1.81 (3) | 2.7363 (19) | 170 (2) |
O5—H5O···N12iii | 0.95 (3) | 1.92 (3) | 2.861 (2) | 172 (2) |
O4—H4O···N11iv | 0.85 (3) | 2.06 (3) | 2.850 (2) | 154 (2) |
O2—H2O···O3 | 0.86 (2) | 1.78 (2) | 2.5940 (18) | 155 (2) |
O6—H6O···O8 | 0.89 (3) | 1.83 (3) | 2.715 (2) | 174 (3) |
Symmetry codes: (ii) x−1, y, z−1; (iii) x, y+1, z+1; (iv) −x+3, −y+1, −z+1. |
C33H22N3O7 | V = 1271.8 Å3 |
Mr = 572.53 | Z = 2 |
Triclinic, P1 | F(000) = 594 |
a = 4.983 Å | Dx = 1.495 Mg m−3 |
b = 15.381 Å | Mo Kα radiation, λ = 0.71073 Å |
c = 18.142 Å | µ = 0.11 mm−1 |
α = 112.21° | T = 150 K |
β = 94.99° | Plate, yellow-red |
γ = 94.92° | 0.50 × 0.20 × 0.10 mm |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | Rint = 0.066 |
Tmin = 0.698, Tmax = 1.000 | θmax = 27.5°, θmin = 3.3° |
13154 measured reflections | h = −6→6 |
5827 independent reflections | k = −19→19 |
3470 reflections with I > 2σ(I) | l = −23→23 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.061 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.155 | w = 1/[σ2(Fo2) + (0.0589P)2 + 0.7384P] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
5827 reflections | Δρmax = 0.24 e Å−3 |
408 parameters | Δρmin = −0.30 e Å−3 |
C33H22N3O7 | γ = 94.92° |
Mr = 572.53 | V = 1271.8 Å3 |
Triclinic, P1 | Z = 2 |
a = 4.983 Å | Mo Kα radiation |
b = 15.381 Å | µ = 0.11 mm−1 |
c = 18.142 Å | T = 150 K |
α = 112.21° | 0.50 × 0.20 × 0.10 mm |
β = 94.99° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 5827 independent reflections |
Tmin = 0.698, Tmax = 1.000 | 3470 reflections with I > 2σ(I) |
13154 measured reflections | Rint = 0.066 |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.24 e Å−3 |
5827 reflections | Δρmin = −0.30 e Å−3 |
408 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
H4O | 0.897 (6) | 0.450 (2) | 0.4194 (19) | 0.042 (10)* | |
H1O | −0.174 (7) | 0.193 (2) | 0.630 (2) | 0.054 (11)* | |
H6O | −0.063 (7) | 0.012 (3) | 0.130 (2) | 0.072 (12)* | |
H2O | 0.670 (8) | 0.464 (3) | 0.636 (2) | 0.083 (13)* | |
H5O | 0.244 (8) | 0.045 (3) | 0.003 (2) | 0.079 (13)* | |
O7 | 0.2104 (3) | 0.25172 (12) | 0.38109 (10) | 0.0204 (4) | |
O1 | −0.2108 (4) | 0.19263 (14) | 0.58067 (12) | 0.0272 (5) | |
O3 | 0.7715 (4) | 0.46014 (12) | 0.54083 (10) | 0.0244 (4) | |
O4 | 0.7986 (4) | 0.40741 (13) | 0.38125 (11) | 0.0252 (4) | |
O5 | 0.3775 (4) | 0.09770 (14) | 0.01924 (10) | 0.0296 (5) | |
N2 | 0.0032 (4) | −0.16528 (15) | 0.28287 (12) | 0.0221 (5) | |
C9 | 0.4138 (5) | 0.29309 (17) | 0.35368 (14) | 0.0175 (5) | |
O2 | 0.5513 (4) | 0.43142 (14) | 0.65876 (11) | 0.0306 (5) | |
N1 | −0.0912 (4) | −0.06573 (15) | 0.18209 (12) | 0.0224 (5) | |
C6 | 0.3897 (5) | 0.34630 (17) | 0.51830 (14) | 0.0191 (5) | |
C7 | 0.5949 (5) | 0.39461 (17) | 0.49231 (15) | 0.0199 (5) | |
O6 | −0.0124 (4) | 0.04668 (13) | 0.09713 (10) | 0.0256 (4) | |
C8 | 0.5994 (5) | 0.36415 (17) | 0.40681 (15) | 0.0196 (5) | |
C2 | −0.0035 (5) | 0.22486 (18) | 0.48112 (15) | 0.0206 (5) | |
H2 | −0.1316 | 0.1781 | 0.4408 | 0.025* | |
C4 | 0.1705 (5) | 0.31474 (18) | 0.62144 (15) | 0.0227 (6) | |
H4 | 0.1575 | 0.3278 | 0.6764 | 0.027* | |
C27 | 0.0690 (5) | −0.13487 (18) | 0.16318 (15) | 0.0215 (6) | |
C21 | −0.1638 (5) | −0.09730 (18) | 0.30031 (15) | 0.0215 (6) | |
C14 | 0.1823 (5) | 0.12182 (17) | 0.14121 (14) | 0.0189 (5) | |
C1 | 0.1995 (5) | 0.27576 (17) | 0.46122 (14) | 0.0189 (5) | |
C16 | −0.2116 (5) | −0.04736 (18) | 0.24869 (15) | 0.0205 (6) | |
C22 | 0.1179 (5) | −0.18541 (18) | 0.21487 (15) | 0.0218 (6) | |
C17 | −0.3922 (5) | 0.02267 (18) | 0.26890 (15) | 0.0238 (6) | |
H17 | −0.4254 | 0.0565 | 0.2355 | 0.029* | |
C15 | 0.1911 (5) | 0.17187 (17) | 0.22267 (14) | 0.0187 (5) | |
H15 | 0.0541 | 0.1556 | 0.2502 | 0.022* | |
C20 | −0.2963 (5) | −0.07494 (19) | 0.37051 (16) | 0.0252 (6) | |
H20 | −0.2648 | −0.1068 | 0.4056 | 0.030* | |
C18 | −0.5165 (5) | 0.04111 (19) | 0.33568 (16) | 0.0257 (6) | |
H18 | −0.6380 | 0.0875 | 0.3483 | 0.031* | |
C12 | 0.5788 (5) | 0.22215 (18) | 0.14083 (15) | 0.0244 (6) | |
H12 | 0.7101 | 0.2401 | 0.1125 | 0.029* | |
C13 | 0.3784 (5) | 0.14676 (18) | 0.09940 (14) | 0.0221 (6) | |
C23 | 0.2887 (6) | −0.25770 (19) | 0.19308 (16) | 0.0285 (6) | |
H23 | 0.3199 | −0.2921 | 0.2262 | 0.034* | |
C19 | −0.4681 (5) | −0.00774 (19) | 0.38712 (16) | 0.0266 (6) | |
H19 | −0.5570 | 0.0067 | 0.4338 | 0.032* | |
C10 | 0.3992 (5) | 0.24667 (17) | 0.26594 (14) | 0.0177 (5) | |
C26 | 0.2002 (6) | −0.15778 (19) | 0.09290 (15) | 0.0280 (6) | |
H26 | 0.1740 | −0.1243 | 0.0589 | 0.034* | |
C11 | 0.5910 (5) | 0.27174 (18) | 0.22289 (15) | 0.0230 (6) | |
H11 | 0.7304 | 0.3231 | 0.2502 | 0.028* | |
C3 | −0.0141 (5) | 0.24416 (17) | 0.56165 (15) | 0.0201 (5) | |
C5 | 0.3702 (5) | 0.36509 (18) | 0.60058 (15) | 0.0222 (6) | |
C25 | 0.3615 (6) | −0.2269 (2) | 0.07451 (17) | 0.0336 (7) | |
H25 | 0.4464 | −0.2421 | 0.0271 | 0.040* | |
C24 | 0.4077 (6) | −0.2779 (2) | 0.12505 (17) | 0.0339 (7) | |
H24 | 0.5226 | −0.3263 | 0.1109 | 0.041* | |
C33 | 0.9084 (6) | 0.5142 (2) | 0.07037 (17) | 0.0325 (7) | |
N3 | 0.8141 (6) | 0.5647 (2) | 0.02978 (17) | 0.0504 (8) | |
C28 | 1.0947 (6) | 0.4490 (2) | 0.04061 (17) | 0.0314 (7) | |
C30 | 1.0988 (6) | 0.4123 (2) | 0.15924 (19) | 0.0378 (7) | |
H30 | 1.1630 | 0.3780 | 0.1896 | 0.045* | |
C31 | 0.9147 (7) | 0.4767 (2) | 0.18863 (18) | 0.0391 (8) | |
H31 | 0.8554 | 0.4863 | 0.2392 | 0.047* | |
C32 | 0.8201 (8) | 0.5254 (3) | 0.1458 (2) | 0.0530 (10) | |
H32 | 0.6922 | 0.5680 | 0.1663 | 0.064* | |
C29 | 1.1860 (8) | 0.3987 (3) | 0.0875 (2) | 0.0524 (10) | |
H29 | 1.3109 | 0.3545 | 0.0681 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O7 | 0.0230 (10) | 0.0222 (9) | 0.0147 (9) | −0.0039 (8) | 0.0018 (7) | 0.0070 (7) |
O1 | 0.0250 (10) | 0.0368 (11) | 0.0234 (11) | −0.0025 (9) | 0.0037 (8) | 0.0168 (9) |
O3 | 0.0260 (10) | 0.0231 (9) | 0.0184 (10) | −0.0051 (8) | −0.0004 (7) | 0.0043 (8) |
O4 | 0.0278 (11) | 0.0262 (10) | 0.0162 (10) | −0.0114 (9) | 0.0002 (8) | 0.0058 (8) |
O5 | 0.0370 (12) | 0.0350 (11) | 0.0110 (9) | −0.0077 (10) | 0.0037 (8) | 0.0050 (8) |
N2 | 0.0236 (12) | 0.0244 (12) | 0.0199 (12) | 0.0020 (10) | 0.0038 (9) | 0.0103 (9) |
C9 | 0.0205 (13) | 0.0180 (12) | 0.0173 (13) | 0.0028 (10) | 0.0051 (10) | 0.0097 (10) |
O2 | 0.0341 (11) | 0.0337 (11) | 0.0161 (10) | −0.0098 (9) | −0.0019 (8) | 0.0051 (8) |
N1 | 0.0220 (12) | 0.0247 (12) | 0.0200 (12) | −0.0021 (10) | −0.0003 (9) | 0.0098 (9) |
C6 | 0.0212 (13) | 0.0184 (12) | 0.0175 (13) | 0.0015 (11) | 0.0025 (10) | 0.0072 (10) |
C7 | 0.0225 (14) | 0.0142 (12) | 0.0204 (13) | 0.0025 (11) | −0.0002 (10) | 0.0046 (10) |
O6 | 0.0328 (11) | 0.0274 (10) | 0.0140 (9) | −0.0074 (9) | −0.0026 (8) | 0.0085 (8) |
C8 | 0.0216 (13) | 0.0177 (13) | 0.0224 (14) | 0.0011 (11) | 0.0043 (10) | 0.0108 (11) |
C2 | 0.0207 (13) | 0.0231 (13) | 0.0178 (13) | −0.0003 (11) | 0.0008 (10) | 0.0088 (10) |
C4 | 0.0274 (15) | 0.0279 (14) | 0.0142 (13) | 0.0032 (12) | 0.0041 (10) | 0.0093 (11) |
C27 | 0.0181 (13) | 0.0247 (14) | 0.0199 (14) | −0.0038 (11) | −0.0016 (10) | 0.0087 (11) |
C21 | 0.0213 (14) | 0.0223 (13) | 0.0207 (14) | −0.0017 (11) | 0.0005 (10) | 0.0096 (11) |
C14 | 0.0234 (14) | 0.0179 (12) | 0.0144 (12) | −0.0021 (11) | −0.0024 (10) | 0.0071 (10) |
C1 | 0.0215 (13) | 0.0202 (13) | 0.0159 (13) | 0.0066 (11) | 0.0024 (10) | 0.0072 (10) |
C16 | 0.0191 (13) | 0.0227 (13) | 0.0184 (13) | −0.0028 (11) | 0.0007 (10) | 0.0082 (11) |
C22 | 0.0212 (14) | 0.0245 (14) | 0.0193 (14) | −0.0007 (11) | 0.0011 (10) | 0.0092 (11) |
C17 | 0.0215 (14) | 0.0239 (14) | 0.0260 (15) | 0.0002 (11) | −0.0022 (11) | 0.0114 (11) |
C15 | 0.0203 (13) | 0.0215 (13) | 0.0149 (13) | −0.0020 (11) | 0.0000 (10) | 0.0093 (10) |
C20 | 0.0250 (14) | 0.0286 (15) | 0.0245 (15) | 0.0002 (12) | 0.0050 (11) | 0.0132 (12) |
C18 | 0.0232 (14) | 0.0241 (14) | 0.0284 (15) | 0.0035 (12) | 0.0026 (11) | 0.0088 (12) |
C12 | 0.0279 (15) | 0.0280 (14) | 0.0178 (14) | −0.0010 (12) | 0.0068 (11) | 0.0098 (11) |
C13 | 0.0271 (14) | 0.0257 (14) | 0.0138 (13) | 0.0025 (12) | 0.0001 (10) | 0.0087 (11) |
C23 | 0.0329 (16) | 0.0279 (15) | 0.0281 (16) | 0.0060 (13) | 0.0060 (12) | 0.0138 (12) |
C19 | 0.0276 (15) | 0.0289 (15) | 0.0229 (15) | 0.0025 (12) | 0.0062 (11) | 0.0093 (12) |
C10 | 0.0201 (13) | 0.0188 (13) | 0.0157 (12) | 0.0037 (11) | 0.0009 (10) | 0.0082 (10) |
C26 | 0.0346 (16) | 0.0317 (15) | 0.0202 (14) | 0.0013 (13) | 0.0042 (12) | 0.0133 (12) |
C11 | 0.0227 (14) | 0.0235 (14) | 0.0221 (14) | −0.0008 (11) | 0.0008 (11) | 0.0094 (11) |
C3 | 0.0191 (13) | 0.0219 (13) | 0.0226 (14) | 0.0046 (11) | 0.0042 (10) | 0.0116 (11) |
C5 | 0.0242 (14) | 0.0227 (14) | 0.0177 (14) | 0.0045 (11) | 0.0003 (10) | 0.0057 (11) |
C25 | 0.0411 (18) | 0.0401 (17) | 0.0202 (15) | 0.0097 (15) | 0.0108 (12) | 0.0100 (13) |
C24 | 0.0400 (18) | 0.0308 (16) | 0.0312 (17) | 0.0108 (14) | 0.0107 (13) | 0.0095 (13) |
C33 | 0.0416 (18) | 0.0315 (16) | 0.0265 (16) | 0.0086 (14) | 0.0061 (13) | 0.0125 (13) |
N3 | 0.065 (2) | 0.0622 (19) | 0.0434 (17) | 0.0392 (17) | 0.0266 (15) | 0.0314 (15) |
C28 | 0.0340 (17) | 0.0333 (16) | 0.0270 (16) | 0.0082 (13) | 0.0052 (12) | 0.0106 (13) |
C30 | 0.0389 (18) | 0.0409 (18) | 0.0408 (19) | 0.0093 (15) | 0.0058 (14) | 0.0229 (15) |
C31 | 0.050 (2) | 0.0385 (18) | 0.0304 (17) | 0.0061 (16) | 0.0096 (14) | 0.0144 (14) |
C32 | 0.076 (3) | 0.059 (2) | 0.043 (2) | 0.042 (2) | 0.0332 (19) | 0.0287 (18) |
C29 | 0.062 (2) | 0.060 (2) | 0.054 (2) | 0.037 (2) | 0.0247 (18) | 0.0335 (19) |
O7—C1 | 1.365 (3) | C22—C23 | 1.416 (4) |
O7—C9 | 1.377 (3) | C17—C18 | 1.354 (4) |
O1—C3 | 1.357 (3) | C17—H17 | 0.9500 |
O1—H1O | 0.90 (3) | C15—C10 | 1.409 (3) |
O3—C7 | 1.268 (3) | C15—H15 | 0.9500 |
O4—C8 | 1.357 (3) | C20—C19 | 1.362 (4) |
O4—H4O | 0.83 (3) | C20—H20 | 0.9500 |
O5—C13 | 1.361 (3) | C18—C19 | 1.420 (4) |
O5—H5O | 0.94 (4) | C18—H18 | 0.9500 |
N2—C22 | 1.345 (3) | C12—C13 | 1.385 (4) |
N2—C21 | 1.353 (3) | C12—C11 | 1.386 (3) |
C9—C8 | 1.362 (3) | C12—H12 | 0.9500 |
C9—C10 | 1.470 (3) | C23—C24 | 1.357 (4) |
O2—C5 | 1.353 (3) | C23—H23 | 0.9500 |
O2—H2O | 0.96 (4) | C19—H19 | 0.9500 |
N1—C16 | 1.340 (3) | C10—C11 | 1.402 (3) |
N1—C27 | 1.343 (3) | C26—C25 | 1.347 (4) |
C6—C1 | 1.397 (3) | C26—H26 | 0.9500 |
C6—C5 | 1.423 (3) | C11—H11 | 0.9500 |
C6—C7 | 1.428 (3) | C25—C24 | 1.431 (4) |
C7—C8 | 1.444 (3) | C25—H25 | 0.9500 |
O6—C14 | 1.375 (3) | C24—H24 | 0.9500 |
O6—H6O | 0.98 (4) | C33—N3 | 1.341 (4) |
C2—C1 | 1.381 (3) | C33—C28 | 1.413 (4) |
C2—C3 | 1.383 (3) | C33—C32 | 1.427 (4) |
C2—H2 | 0.9500 | N3—C28i | 1.340 (4) |
C4—C5 | 1.374 (4) | C28—N3i | 1.340 (4) |
C4—C3 | 1.402 (4) | C28—C29 | 1.422 (4) |
C4—H4 | 0.9500 | C30—C29 | 1.355 (4) |
C27—C26 | 1.422 (4) | C30—C31 | 1.396 (4) |
C27—C22 | 1.445 (3) | C30—H30 | 0.9500 |
C21—C20 | 1.425 (3) | C31—C32 | 1.351 (4) |
C21—C16 | 1.435 (3) | C31—H31 | 0.9500 |
C14—C15 | 1.379 (3) | C32—H32 | 0.9500 |
C14—C13 | 1.401 (3) | C29—H29 | 0.9500 |
C16—C17 | 1.425 (4) | ||
C1—O7—C9 | 121.52 (19) | C17—C18—H18 | 119.5 |
C3—O1—H1O | 113 (2) | C19—C18—H18 | 119.5 |
C8—O4—H4O | 112 (2) | C13—C12—C11 | 121.1 (2) |
C13—O5—H5O | 108 (2) | C13—C12—H12 | 119.5 |
C22—N2—C21 | 117.6 (2) | C11—C12—H12 | 119.5 |
C8—C9—O7 | 120.0 (2) | O5—C13—C12 | 119.5 (2) |
C8—C9—C10 | 129.3 (2) | O5—C13—C14 | 121.3 (2) |
O7—C9—C10 | 110.7 (2) | C12—C13—C14 | 119.2 (2) |
C5—O2—H2O | 111 (2) | C24—C23—C22 | 120.1 (3) |
C16—N1—C27 | 118.1 (2) | C24—C23—H23 | 119.9 |
C1—C6—C5 | 117.3 (2) | C22—C23—H23 | 119.9 |
C1—C6—C7 | 119.5 (2) | C20—C19—C18 | 120.9 (3) |
C5—C6—C7 | 123.2 (2) | C20—C19—H19 | 119.5 |
O3—C7—C6 | 122.7 (2) | C18—C19—H19 | 119.5 |
O3—C7—C8 | 120.2 (2) | C11—C10—C15 | 117.9 (2) |
C6—C7—C8 | 117.0 (2) | C11—C10—C9 | 122.5 (2) |
C14—O6—H6O | 109 (2) | C15—C10—C9 | 119.6 (2) |
O4—C8—C9 | 121.1 (2) | C25—C26—C27 | 120.1 (3) |
O4—C8—C7 | 117.7 (2) | C25—C26—H26 | 119.9 |
C9—C8—C7 | 121.2 (2) | C27—C26—H26 | 119.9 |
C1—C2—C3 | 117.9 (2) | C12—C11—C10 | 120.5 (2) |
C1—C2—H2 | 121.1 | C12—C11—H11 | 119.7 |
C3—C2—H2 | 121.1 | C10—C11—H11 | 119.7 |
C5—C4—C3 | 120.1 (2) | O1—C3—C2 | 117.5 (2) |
C5—C4—H4 | 120.0 | O1—C3—C4 | 121.2 (2) |
C3—C4—H4 | 120.0 | C2—C3—C4 | 121.3 (2) |
N1—C27—C26 | 120.4 (2) | O2—C5—C4 | 119.5 (2) |
N1—C27—C22 | 120.8 (2) | O2—C5—C6 | 120.2 (2) |
C26—C27—C22 | 118.7 (2) | C4—C5—C6 | 120.2 (2) |
N2—C21—C20 | 119.9 (2) | C26—C25—C24 | 121.3 (3) |
N2—C21—C16 | 120.9 (2) | C26—C25—H25 | 119.4 |
C20—C21—C16 | 119.1 (2) | C24—C25—H25 | 119.4 |
O6—C14—C15 | 123.3 (2) | C23—C24—C25 | 120.5 (3) |
O6—C14—C13 | 116.8 (2) | C23—C24—H24 | 119.7 |
C15—C14—C13 | 120.0 (2) | C25—C24—H24 | 119.7 |
O7—C1—C2 | 116.1 (2) | N3—C33—C28 | 122.0 (3) |
O7—C1—C6 | 120.7 (2) | N3—C33—C32 | 120.0 (3) |
C2—C1—C6 | 123.2 (2) | C28—C33—C32 | 118.1 (3) |
N1—C16—C17 | 119.7 (2) | C28i—N3—C33 | 117.1 (3) |
N1—C16—C21 | 121.3 (2) | N3i—C28—C33 | 121.0 (3) |
C17—C16—C21 | 118.9 (2) | N3i—C28—C29 | 120.5 (3) |
N2—C22—C23 | 119.6 (2) | C33—C28—C29 | 118.5 (3) |
N2—C22—C27 | 121.2 (2) | C29—C30—C31 | 120.1 (3) |
C23—C22—C27 | 119.2 (2) | C29—C30—H30 | 119.9 |
C18—C17—C16 | 120.1 (2) | C31—C30—H30 | 119.9 |
C18—C17—H17 | 119.9 | C32—C31—C30 | 120.5 (3) |
C16—C17—H17 | 119.9 | C32—C31—H31 | 119.7 |
C14—C15—C10 | 121.4 (2) | C30—C31—H31 | 119.7 |
C14—C15—H15 | 119.3 | C31—C32—C33 | 121.4 (3) |
C10—C15—H15 | 119.3 | C31—C32—H32 | 119.3 |
C19—C20—C21 | 119.8 (2) | C33—C32—H32 | 119.3 |
C19—C20—H20 | 120.1 | C30—C29—C28 | 121.4 (3) |
C21—C20—H20 | 120.1 | C30—C29—H29 | 119.3 |
C17—C18—C19 | 121.1 (3) | C28—C29—H29 | 119.3 |
Symmetry code: (i) −x+2, −y+1, −z. |
C29H21N2O7S | V = 1247.8 (2) Å3 |
Mr = 541.54 | Z = 2 |
Triclinic, P1 | F(000) = 562 |
a = 9.8066 (9) Å | Dx = 1.441 Mg m−3 |
b = 10.4874 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 13.0073 (12) Å | µ = 0.18 mm−1 |
α = 97.993 (7)° | T = 150 K |
β = 94.646 (7)° | Plate, yellow red |
γ = 108.150 (8)° | 0.55 × 0.20 × 0.15 mm |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | Rint = 0.031 |
Tmin = 0.835, Tmax = 1.000 | θmax = 27.5°, θmin = 3.2° |
13323 measured reflections | h = −12→12 |
5709 independent reflections | k = −13→13 |
4354 reflections with I > 2σ(I) | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.065P)2 + 0.7749P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
5709 reflections | Δρmax = 0.42 e Å−3 |
372 parameters | Δρmin = −0.67 e Å−3 |
C29H21N2O7S | γ = 108.150 (8)° |
Mr = 541.54 | V = 1247.8 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.8066 (9) Å | Mo Kα radiation |
b = 10.4874 (10) Å | µ = 0.18 mm−1 |
c = 13.0073 (12) Å | T = 150 K |
α = 97.993 (7)° | 0.55 × 0.20 × 0.15 mm |
β = 94.646 (7)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 5709 independent reflections |
Tmin = 0.835, Tmax = 1.000 | 4354 reflections with I > 2σ(I) |
13323 measured reflections | Rint = 0.031 |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.42 e Å−3 |
5709 reflections | Δρmin = −0.67 e Å−3 |
372 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.93446 (8) | 0.65287 (9) | 0.09633 (6) | 0.0491 (2) | |
C29 | 0.9362 (3) | 0.5207 (3) | 0.0028 (2) | 0.0335 (6) | |
C28 | 0.8053 (3) | 0.4682 (3) | −0.0601 (2) | 0.0397 (6) | |
H28 | 0.7845 | 0.3954 | −0.1176 | 0.048* | |
C26 | 0.7595 (3) | 0.6361 (3) | 0.0520 (2) | 0.0476 (7) | |
H26 | 0.7074 | 0.6916 | 0.0816 | 0.057* | |
C27 | 0.7051 (3) | 0.5329 (3) | −0.0311 (2) | 0.0433 (7) | |
H27 | 0.6092 | 0.5072 | −0.0660 | 0.052* | |
O7 | 0.41248 (14) | 0.84127 (14) | 0.07091 (9) | 0.0149 (3) | |
O5 | 0.35416 (15) | 0.83577 (14) | −0.39102 (10) | 0.0175 (3) | |
O6 | 0.56244 (16) | 0.71507 (15) | −0.38149 (10) | 0.0191 (3) | |
O4 | 0.15529 (19) | 0.93991 (19) | −0.08760 (11) | 0.0315 (4) | |
O1 | 0.48913 (16) | 0.83258 (15) | 0.43301 (10) | 0.0174 (3) | |
O2 | 0.13144 (16) | 1.00488 (16) | 0.30913 (11) | 0.0223 (3) | |
O3 | 0.09372 (16) | 1.00750 (16) | 0.10788 (11) | 0.0242 (3) | |
C6 | 0.2675 (2) | 0.9241 (2) | 0.18516 (14) | 0.0149 (4) | |
N2 | 1.30350 (19) | 0.27371 (18) | −0.39338 (13) | 0.0217 (4) | |
C9 | 0.3387 (2) | 0.8630 (2) | −0.01546 (14) | 0.0153 (4) | |
C7 | 0.1914 (2) | 0.9537 (2) | 0.09839 (15) | 0.0182 (4) | |
C2 | 0.4540 (2) | 0.83446 (19) | 0.24895 (14) | 0.0148 (4) | |
H2 | 0.5274 | 0.7952 | 0.2357 | 0.018* | |
C12 | 0.4050 (2) | 0.81145 (19) | −0.29738 (14) | 0.0137 (4) | |
N1 | 0.76683 (19) | 0.59628 (18) | −0.34836 (13) | 0.0219 (4) | |
C18 | 0.9760 (2) | 0.4639 (2) | −0.35992 (15) | 0.0180 (4) | |
C4 | 0.3117 (2) | 0.91837 (19) | 0.37024 (14) | 0.0149 (4) | |
H4 | 0.2906 | 0.9356 | 0.4398 | 0.018* | |
C1 | 0.3774 (2) | 0.86724 (19) | 0.16890 (14) | 0.0136 (4) | |
C25 | 1.2275 (2) | 0.4568 (2) | −0.31587 (17) | 0.0225 (4) | |
H25 | 1.2519 | 0.5415 | −0.2697 | 0.027* | |
C11 | 0.3467 (2) | 0.84729 (19) | −0.20941 (14) | 0.0144 (4) | |
H11 | 0.2734 | 0.8885 | −0.2151 | 0.017* | |
C14 | 0.5606 (2) | 0.7262 (2) | −0.19454 (15) | 0.0176 (4) | |
H14 | 0.6335 | 0.6845 | −0.1892 | 0.021* | |
C10 | 0.3947 (2) | 0.82332 (19) | −0.11110 (14) | 0.0146 (4) | |
C17 | 0.8466 (2) | 0.4167 (2) | −0.42742 (16) | 0.0202 (4) | |
H17 | 0.8273 | 0.3380 | −0.4795 | 0.024* | |
C5 | 0.2362 (2) | 0.9496 (2) | 0.28945 (14) | 0.0155 (4) | |
C3 | 0.4201 (2) | 0.86092 (19) | 0.34974 (14) | 0.0140 (4) | |
C21 | 1.0881 (2) | 0.3962 (2) | −0.36952 (15) | 0.0176 (4) | |
C15 | 0.5030 (2) | 0.7625 (2) | −0.10600 (14) | 0.0176 (4) | |
H15 | 0.5375 | 0.7459 | −0.0405 | 0.021* | |
C13 | 0.5132 (2) | 0.74986 (19) | −0.29125 (14) | 0.0146 (4) | |
C8 | 0.2301 (2) | 0.9172 (2) | −0.00386 (14) | 0.0191 (4) | |
C16 | 0.7457 (2) | 0.4839 (2) | −0.41896 (16) | 0.0211 (4) | |
H16 | 0.6576 | 0.4487 | −0.4654 | 0.025* | |
C22 | 1.0605 (2) | 0.2716 (2) | −0.43494 (17) | 0.0251 (5) | |
H22 | 0.9668 | 0.2255 | −0.4727 | 0.030* | |
C19 | 0.9960 (2) | 0.5787 (2) | −0.28413 (17) | 0.0250 (5) | |
H19 | 1.0812 | 0.6140 | −0.2348 | 0.030* | |
C24 | 1.3302 (2) | 0.3927 (2) | −0.33045 (17) | 0.0238 (5) | |
H24 | 1.4248 | 0.4360 | −0.2935 | 0.029* | |
C20 | 0.8899 (2) | 0.6405 (2) | −0.28179 (18) | 0.0272 (5) | |
H20 | 0.9054 | 0.7187 | −0.2300 | 0.033* | |
C23 | 1.1702 (2) | 0.2152 (2) | −0.44478 (18) | 0.0270 (5) | |
H23 | 1.1493 | 0.1306 | −0.4904 | 0.032* | |
H5O | 0.409 (3) | 0.830 (3) | −0.434 (2) | 0.034 (7)* | |
H4O | 0.089 (3) | 0.961 (3) | −0.069 (2) | 0.048 (9)* | |
H6O | 0.626 (3) | 0.689 (3) | −0.370 (2) | 0.048 (9)* | |
H2O | 0.106 (3) | 1.020 (3) | 0.252 (2) | 0.048 (9)* | |
H1O | 0.554 (3) | 0.804 (3) | 0.421 (2) | 0.046 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0404 (4) | 0.0678 (5) | 0.0392 (4) | 0.0216 (4) | −0.0016 (3) | 0.0050 (3) |
C29 | 0.0287 (12) | 0.0344 (13) | 0.0384 (13) | 0.0052 (10) | 0.0048 (11) | 0.0211 (11) |
C28 | 0.0312 (13) | 0.0328 (14) | 0.0503 (16) | 0.0042 (11) | −0.0063 (12) | 0.0132 (12) |
C26 | 0.0439 (16) | 0.063 (2) | 0.0460 (16) | 0.0264 (15) | 0.0073 (13) | 0.0232 (14) |
C27 | 0.0313 (14) | 0.0469 (16) | 0.0553 (17) | 0.0111 (12) | 0.0000 (13) | 0.0277 (14) |
O7 | 0.0178 (7) | 0.0252 (7) | 0.0063 (6) | 0.0140 (6) | 0.0017 (5) | 0.0020 (5) |
O5 | 0.0205 (7) | 0.0299 (8) | 0.0077 (6) | 0.0148 (6) | 0.0038 (6) | 0.0050 (5) |
O6 | 0.0222 (8) | 0.0325 (8) | 0.0113 (6) | 0.0201 (7) | 0.0058 (6) | 0.0041 (6) |
O4 | 0.0338 (9) | 0.0690 (12) | 0.0100 (7) | 0.0420 (9) | 0.0044 (6) | 0.0082 (7) |
O1 | 0.0206 (7) | 0.0302 (8) | 0.0093 (6) | 0.0182 (6) | 0.0034 (5) | 0.0055 (5) |
O2 | 0.0253 (8) | 0.0408 (9) | 0.0111 (7) | 0.0254 (7) | 0.0038 (6) | 0.0038 (6) |
O3 | 0.0244 (8) | 0.0452 (9) | 0.0144 (7) | 0.0275 (7) | 0.0034 (6) | 0.0051 (6) |
C6 | 0.0149 (9) | 0.0227 (10) | 0.0102 (8) | 0.0108 (8) | 0.0017 (7) | 0.0025 (7) |
N2 | 0.0248 (9) | 0.0300 (10) | 0.0178 (8) | 0.0179 (8) | 0.0057 (7) | 0.0064 (7) |
C9 | 0.0165 (9) | 0.0228 (10) | 0.0097 (8) | 0.0107 (8) | −0.0001 (7) | 0.0043 (7) |
C7 | 0.0187 (10) | 0.0260 (11) | 0.0139 (9) | 0.0132 (8) | 0.0018 (8) | 0.0028 (8) |
C2 | 0.0148 (9) | 0.0213 (10) | 0.0122 (9) | 0.0110 (8) | 0.0027 (7) | 0.0029 (7) |
C12 | 0.0144 (9) | 0.0187 (9) | 0.0088 (8) | 0.0070 (7) | 0.0004 (7) | 0.0022 (7) |
N1 | 0.0216 (9) | 0.0279 (10) | 0.0227 (9) | 0.0165 (8) | 0.0064 (7) | 0.0038 (7) |
C18 | 0.0165 (10) | 0.0196 (10) | 0.0213 (10) | 0.0097 (8) | 0.0055 (8) | 0.0042 (8) |
C4 | 0.0166 (9) | 0.0228 (10) | 0.0088 (8) | 0.0108 (8) | 0.0047 (7) | 0.0023 (7) |
C1 | 0.0155 (9) | 0.0197 (10) | 0.0085 (8) | 0.0092 (7) | 0.0036 (7) | 0.0027 (7) |
C25 | 0.0218 (11) | 0.0221 (11) | 0.0262 (11) | 0.0122 (8) | 0.0014 (9) | 0.0022 (8) |
C11 | 0.0143 (9) | 0.0193 (9) | 0.0123 (9) | 0.0093 (7) | 0.0018 (7) | 0.0030 (7) |
C14 | 0.0191 (10) | 0.0241 (10) | 0.0150 (9) | 0.0145 (8) | 0.0026 (8) | 0.0034 (8) |
C10 | 0.0153 (9) | 0.0204 (10) | 0.0109 (8) | 0.0104 (7) | 0.0024 (7) | 0.0014 (7) |
C17 | 0.0205 (10) | 0.0222 (10) | 0.0206 (10) | 0.0117 (8) | 0.0028 (8) | 0.0014 (8) |
C5 | 0.0158 (9) | 0.0225 (10) | 0.0115 (9) | 0.0113 (8) | 0.0030 (7) | 0.0016 (7) |
C3 | 0.0168 (9) | 0.0169 (9) | 0.0108 (8) | 0.0086 (7) | 0.0010 (7) | 0.0036 (7) |
C21 | 0.0182 (10) | 0.0204 (10) | 0.0182 (9) | 0.0106 (8) | 0.0063 (8) | 0.0045 (8) |
C15 | 0.0193 (10) | 0.0272 (11) | 0.0117 (9) | 0.0149 (8) | 0.0017 (7) | 0.0046 (7) |
C13 | 0.0167 (9) | 0.0203 (10) | 0.0093 (8) | 0.0095 (7) | 0.0038 (7) | 0.0015 (7) |
C8 | 0.0209 (10) | 0.0322 (11) | 0.0097 (9) | 0.0168 (9) | 0.0007 (8) | 0.0038 (8) |
C16 | 0.0192 (10) | 0.0273 (11) | 0.0202 (10) | 0.0121 (8) | 0.0021 (8) | 0.0049 (8) |
C22 | 0.0176 (10) | 0.0291 (12) | 0.0282 (11) | 0.0115 (9) | 0.0001 (9) | −0.0033 (9) |
C19 | 0.0200 (10) | 0.0273 (12) | 0.0278 (11) | 0.0120 (9) | −0.0018 (9) | −0.0026 (9) |
C24 | 0.0185 (10) | 0.0285 (11) | 0.0260 (11) | 0.0115 (9) | −0.0010 (9) | 0.0038 (9) |
C20 | 0.0258 (11) | 0.0297 (12) | 0.0280 (11) | 0.0162 (9) | 0.0015 (9) | −0.0043 (9) |
C23 | 0.0270 (12) | 0.0278 (12) | 0.0292 (11) | 0.0165 (9) | 0.0041 (9) | −0.0030 (9) |
S1—C26 | 1.712 (3) | C2—H2 | 0.9500 |
S1—C29 | 1.718 (3) | C12—C11 | 1.378 (3) |
C29—C28 | 1.373 (3) | C12—C13 | 1.406 (3) |
C29—C29i | 1.450 (5) | N1—C20 | 1.338 (3) |
C28—C27 | 1.405 (4) | N1—C16 | 1.338 (3) |
C28—H28 | 0.9500 | C18—C17 | 1.391 (3) |
C26—C27 | 1.359 (4) | C18—C19 | 1.397 (3) |
C26—H26 | 0.9500 | C18—C21 | 1.488 (3) |
C27—H27 | 0.9500 | C4—C5 | 1.371 (3) |
O7—C1 | 1.360 (2) | C4—C3 | 1.402 (2) |
O7—C9 | 1.371 (2) | C4—H4 | 0.9500 |
O5—C12 | 1.365 (2) | C25—C24 | 1.386 (3) |
O5—H5O | 0.82 (3) | C25—C21 | 1.393 (3) |
O6—C13 | 1.352 (2) | C25—H25 | 0.9500 |
O6—H6O | 0.77 (3) | C11—C10 | 1.409 (2) |
O4—C8 | 1.354 (2) | C11—H11 | 0.9500 |
O4—H4O | 0.80 (3) | C14—C15 | 1.381 (3) |
O1—C3 | 1.347 (2) | C14—C13 | 1.387 (3) |
O1—H1O | 0.80 (3) | C14—H14 | 0.9500 |
O2—C5 | 1.352 (2) | C10—C15 | 1.401 (3) |
O2—H2O | 0.81 (3) | C17—C16 | 1.385 (3) |
O3—C7 | 1.260 (2) | C17—H17 | 0.9500 |
C6—C1 | 1.402 (2) | C21—C22 | 1.392 (3) |
C6—C5 | 1.423 (2) | C15—H15 | 0.9500 |
C6—C7 | 1.426 (3) | C16—H16 | 0.9500 |
N2—C24 | 1.332 (3) | C22—C23 | 1.386 (3) |
N2—C23 | 1.333 (3) | C22—H22 | 0.9500 |
C9—C8 | 1.363 (3) | C19—C20 | 1.387 (3) |
C9—C10 | 1.460 (2) | C19—H19 | 0.9500 |
C7—C8 | 1.446 (3) | C24—H24 | 0.9500 |
C2—C1 | 1.379 (2) | C20—H20 | 0.9500 |
C2—C3 | 1.390 (2) | C23—H23 | 0.9500 |
C26—S1—C29 | 92.61 (14) | C12—C11—C10 | 120.59 (17) |
C28—C29—C29i | 128.8 (3) | C12—C11—H11 | 119.7 |
C28—C29—S1 | 110.0 (2) | C10—C11—H11 | 119.7 |
C29i—C29—S1 | 121.2 (3) | C15—C14—C13 | 120.76 (17) |
C29—C28—C27 | 113.3 (3) | C15—C14—H14 | 119.6 |
C29—C28—H28 | 123.4 | C13—C14—H14 | 119.6 |
C27—C28—H28 | 123.4 | C15—C10—C11 | 117.96 (16) |
C27—C26—S1 | 111.0 (2) | C15—C10—C9 | 119.63 (16) |
C27—C26—H26 | 124.5 | C11—C10—C9 | 122.39 (16) |
S1—C26—H26 | 124.5 | C16—C17—C18 | 120.24 (18) |
C26—C27—C28 | 113.1 (3) | C16—C17—H17 | 119.9 |
C26—C27—H27 | 123.5 | C18—C17—H17 | 119.9 |
C28—C27—H27 | 123.5 | O2—C5—C4 | 119.78 (16) |
C1—O7—C9 | 122.05 (14) | O2—C5—C6 | 119.89 (16) |
C12—O5—H5O | 110.2 (19) | C4—C5—C6 | 120.33 (16) |
C13—O6—H6O | 110 (2) | O1—C3—C2 | 121.99 (16) |
C8—O4—H4O | 109 (2) | O1—C3—C4 | 116.28 (16) |
C3—O1—H1O | 115 (2) | C2—C3—C4 | 121.73 (16) |
C5—O2—H2O | 103 (2) | C22—C21—C25 | 116.81 (18) |
C1—C6—C5 | 117.72 (16) | C22—C21—C18 | 121.78 (18) |
C1—C6—C7 | 119.79 (16) | C25—C21—C18 | 121.38 (18) |
C5—C6—C7 | 122.50 (16) | C14—C15—C10 | 121.18 (17) |
C24—N2—C23 | 117.16 (17) | C14—C15—H15 | 119.4 |
C8—C9—O7 | 119.85 (16) | C10—C15—H15 | 119.4 |
C8—C9—C10 | 128.96 (17) | O6—C13—C14 | 124.15 (17) |
O7—C9—C10 | 111.19 (15) | O6—C13—C12 | 117.21 (16) |
O3—C7—C6 | 122.98 (17) | C14—C13—C12 | 118.64 (16) |
O3—C7—C8 | 120.37 (17) | O4—C8—C9 | 121.24 (17) |
C6—C7—C8 | 116.65 (16) | O4—C8—C7 | 117.50 (17) |
C1—C2—C3 | 117.66 (16) | C9—C8—C7 | 121.27 (17) |
C1—C2—H2 | 121.2 | N1—C16—C17 | 122.97 (19) |
C3—C2—H2 | 121.2 | N1—C16—H16 | 118.5 |
O5—C12—C11 | 118.43 (16) | C17—C16—H16 | 118.5 |
O5—C12—C13 | 120.70 (16) | C23—C22—C21 | 119.7 (2) |
C11—C12—C13 | 120.86 (16) | C23—C22—H22 | 120.1 |
C20—N1—C16 | 117.00 (17) | C21—C22—H22 | 120.1 |
C17—C18—C19 | 116.75 (18) | C20—C19—C18 | 119.2 (2) |
C17—C18—C21 | 121.29 (17) | C20—C19—H19 | 120.4 |
C19—C18—C21 | 121.96 (18) | C18—C19—H19 | 120.4 |
C5—C4—C3 | 119.73 (16) | N2—C24—C25 | 123.58 (19) |
C5—C4—H4 | 120.1 | N2—C24—H24 | 118.2 |
C3—C4—H4 | 120.1 | C25—C24—H24 | 118.2 |
O7—C1—C2 | 116.87 (16) | N1—C20—C19 | 123.8 (2) |
O7—C1—C6 | 120.29 (16) | N1—C20—H20 | 118.1 |
C2—C1—C6 | 122.84 (16) | C19—C20—H20 | 118.1 |
C24—C25—C21 | 119.45 (19) | N2—C23—C22 | 123.3 (2) |
C24—C25—H25 | 120.3 | N2—C23—H23 | 118.4 |
C21—C25—H25 | 120.3 | C22—C23—H23 | 118.4 |
Symmetry code: (i) −x+2, −y+1, −z. |
C69H50N6O14S6 | V = 3040.5 (9) Å3 |
Mr = 1379.51 | Z = 2 |
Triclinic, P1 | F(000) = 1428 |
a = 12.547 (2) Å | Dx = 1.507 Mg m−3 |
b = 13.299 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 18.490 (3) Å | µ = 0.30 mm−1 |
α = 94.246 (7)° | T = 150 K |
β = 90.204 (6)° | Plate, yellow red |
γ = 98.776 (7)° | 0.50 × 0.30 × 0.20 mm |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | Rint = 0.064 |
Tmin = 0.696, Tmax = 1.000 | θmax = 27.5°, θmin = 3.1° |
31942 measured reflections | h = −16→16 |
13902 independent reflections | k = −17→17 |
9440 reflections with I > 2σ(I) | l = −23→23 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.067 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.188 | w = 1/[σ2(Fo2) + (0.0877P)2 + 2.2248P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
13902 reflections | Δρmax = 0.87 e Å−3 |
896 parameters | Δρmin = −0.68 e Å−3 |
C69H50N6O14S6 | γ = 98.776 (7)° |
Mr = 1379.51 | V = 3040.5 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.547 (2) Å | Mo Kα radiation |
b = 13.299 (2) Å | µ = 0.30 mm−1 |
c = 18.490 (3) Å | T = 150 K |
α = 94.246 (7)° | 0.50 × 0.30 × 0.20 mm |
β = 90.204 (6)° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 13902 independent reflections |
Tmin = 0.696, Tmax = 1.000 | 9440 reflections with I > 2σ(I) |
31942 measured reflections | Rint = 0.064 |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.188 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.87 e Å−3 |
13902 reflections | Δρmin = −0.68 e Å−3 |
896 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.39764 (6) | 0.09172 (6) | 0.42113 (4) | 0.02333 (19) | |
S2 | 0.43288 (7) | 0.14268 (7) | 0.57952 (4) | 0.0262 (2) | |
S3 | 0.65489 (7) | 0.14950 (7) | 0.39598 (5) | 0.0256 (2) | |
S4 | 0.69273 (7) | 0.19190 (6) | 0.55484 (5) | 0.0259 (2) | |
O7 | 0.12473 (16) | −0.22271 (16) | 0.76185 (11) | 0.0188 (5) | |
O6 | 0.25996 (19) | 0.24133 (18) | 0.72198 (13) | 0.0283 (6) | |
O14 | 0.11503 (16) | 0.31605 (15) | 0.33420 (11) | 0.0187 (5) | |
O1 | 0.2160 (2) | −0.55859 (18) | 0.73842 (14) | 0.0285 (6) | |
O13 | −0.00457 (18) | −0.14436 (18) | 0.38910 (13) | 0.0225 (5) | |
O10 | 0.38566 (17) | 0.40896 (17) | 0.22100 (12) | 0.0238 (5) | |
O8 | 0.03169 (19) | 0.65271 (17) | 0.36606 (14) | 0.0262 (6) | |
O11 | 0.34057 (19) | 0.21009 (17) | 0.25171 (13) | 0.0232 (5) | |
O9 | 0.33887 (19) | 0.59617 (18) | 0.23237 (14) | 0.0279 (6) | |
O4 | −0.06711 (19) | −0.10746 (17) | 0.87447 (13) | 0.0262 (5) | |
O12 | 0.15849 (19) | −0.12891 (16) | 0.29277 (13) | 0.0246 (5) | |
O5 | 0.07218 (19) | 0.22260 (17) | 0.79526 (14) | 0.0292 (6) | |
O2 | −0.0777 (2) | −0.4951 (2) | 0.88345 (17) | 0.0422 (8) | |
C8 | −0.0145 (2) | −0.1790 (2) | 0.84042 (17) | 0.0200 (7) | |
O3 | −0.1230 (2) | −0.30972 (18) | 0.89685 (14) | 0.0344 (6) | |
C6 | 0.0198 (2) | −0.3555 (2) | 0.82422 (17) | 0.0211 (7) | |
C1 | 0.1044 (2) | −0.3229 (2) | 0.77792 (16) | 0.0182 (6) | |
C22 | 0.3018 (2) | 0.3824 (2) | 0.25605 (16) | 0.0188 (6) | |
C24 | 0.1813 (2) | 0.2459 (2) | 0.31101 (16) | 0.0177 (6) | |
C14 | 0.2619 (2) | 0.0629 (2) | 0.72423 (17) | 0.0212 (7) | |
H14 | 0.3290 | 0.0707 | 0.7000 | 0.025* | |
C19 | 0.1844 (2) | 0.6236 (2) | 0.29936 (18) | 0.0214 (7) | |
H19 | 0.1987 | 0.6943 | 0.2920 | 0.026* | |
C18 | 0.0944 (2) | 0.5847 (2) | 0.33931 (18) | 0.0208 (7) | |
C26 | 0.1740 (2) | 0.0553 (2) | 0.30185 (16) | 0.0184 (6) | |
H26 | 0.2307 | 0.0613 | 0.2678 | 0.022* | |
C64 | 0.4909 (2) | 0.1323 (2) | 0.49310 (16) | 0.0186 (6) | |
C7 | −0.0452 (2) | −0.2846 (2) | 0.85585 (17) | 0.0217 (7) | |
C25 | 0.1373 (2) | 0.1439 (2) | 0.33251 (17) | 0.0177 (6) | |
C23 | 0.2730 (2) | 0.2768 (2) | 0.27363 (16) | 0.0185 (6) | |
C28 | 0.0434 (2) | −0.0505 (2) | 0.37124 (16) | 0.0169 (6) | |
C11 | 0.0670 (2) | 0.0393 (2) | 0.79583 (16) | 0.0183 (6) | |
H11 | −0.0001 | 0.0317 | 0.8201 | 0.022* | |
N5 | −0.2342 (2) | −0.1388 (2) | 0.96415 (16) | 0.0271 (6) | |
C12 | 0.1141 (2) | 0.1353 (2) | 0.77842 (17) | 0.0208 (7) | |
C16 | 0.1399 (2) | 0.4174 (2) | 0.32190 (16) | 0.0173 (6) | |
C29 | 0.0083 (2) | 0.0366 (2) | 0.40234 (17) | 0.0193 (6) | |
H29 | −0.0479 | 0.0305 | 0.4368 | 0.023* | |
C63 | 0.5979 (3) | 0.1549 (2) | 0.48312 (17) | 0.0212 (7) | |
C2 | 0.1701 (2) | −0.3882 (2) | 0.74665 (17) | 0.0207 (7) | |
H2 | 0.2251 | −0.3646 | 0.7141 | 0.025* | |
C27 | 0.1279 (2) | −0.0404 (2) | 0.32099 (16) | 0.0172 (6) | |
C30 | 0.0545 (2) | 0.1325 (2) | 0.38354 (17) | 0.0190 (6) | |
H30 | 0.0297 | 0.1914 | 0.4055 | 0.023* | |
C9 | 0.0692 (2) | −0.1505 (2) | 0.79582 (16) | 0.0175 (6) | |
C10 | 0.1166 (2) | −0.0475 (2) | 0.77831 (16) | 0.0185 (6) | |
C17 | 0.0717 (2) | 0.4815 (2) | 0.35094 (17) | 0.0201 (7) | |
H17 | 0.0109 | 0.4558 | 0.3782 | 0.024* | |
C21 | 0.2309 (2) | 0.4521 (2) | 0.28174 (17) | 0.0191 (6) | |
C3 | 0.1534 (3) | −0.4895 (2) | 0.76428 (18) | 0.0228 (7) | |
C66 | 0.3004 (3) | 0.1018 (3) | 0.54760 (19) | 0.0261 (7) | |
H66 | 0.2413 | 0.0966 | 0.5798 | 0.031* | |
C15 | 0.2154 (2) | −0.0329 (2) | 0.74257 (16) | 0.0198 (7) | |
H15 | 0.2512 | −0.0898 | 0.7307 | 0.024* | |
N6 | −0.6658 (2) | −0.1079 (2) | 1.20788 (16) | 0.0296 (7) | |
C20 | 0.2520 (2) | 0.5585 (2) | 0.27089 (17) | 0.0211 (7) | |
C4 | 0.0710 (3) | −0.5256 (3) | 0.81020 (19) | 0.0263 (8) | |
H4 | 0.0610 | −0.5949 | 0.8216 | 0.032* | |
C5 | 0.0040 (3) | −0.4604 (3) | 0.83919 (19) | 0.0263 (8) | |
C13 | 0.2119 (2) | 0.1474 (2) | 0.74069 (17) | 0.0203 (7) | |
C56 | −0.4965 (3) | −0.1278 (3) | 1.11161 (18) | 0.0246 (7) | |
C53 | −0.4051 (3) | −0.1355 (3) | 1.06085 (18) | 0.0240 (7) | |
C65 | 0.2858 (3) | 0.0785 (2) | 0.47714 (18) | 0.0246 (7) | |
H65 | 0.2156 | 0.0551 | 0.4574 | 0.030* | |
C62 | 0.8038 (3) | 0.2101 (3) | 0.4980 (2) | 0.0323 (8) | |
H62 | 0.8743 | 0.2330 | 0.5173 | 0.039* | |
C57 | −0.4976 (3) | −0.1654 (3) | 1.1790 (2) | 0.0356 (9) | |
H57 | −0.4399 | −0.1978 | 1.1945 | 0.043* | |
C61 | 0.7870 (3) | 0.1912 (3) | 0.4274 (2) | 0.0307 (8) | |
H61 | 0.8452 | 0.2001 | 0.3946 | 0.037* | |
C59 | −0.6623 (3) | −0.0669 (3) | 1.1433 (2) | 0.0395 (9) | |
H59 | −0.7183 | −0.0301 | 1.1313 | 0.047* | |
C54 | −0.3004 (3) | −0.1067 (3) | 1.0838 (2) | 0.0335 (9) | |
H54 | −0.2844 | −0.0857 | 1.1333 | 0.040* | |
C58 | −0.5843 (3) | −0.1554 (3) | 1.2242 (2) | 0.0370 (9) | |
H58 | −0.5852 | −0.1845 | 1.2697 | 0.044* | |
C55 | −0.2177 (3) | −0.1081 (3) | 1.0343 (2) | 0.0367 (9) | |
H55 | −0.1457 | −0.0861 | 1.0511 | 0.044* | |
C60 | −0.5807 (3) | −0.0759 (3) | 1.0932 (2) | 0.0383 (9) | |
H60 | −0.5822 | −0.0474 | 1.0477 | 0.046* | |
C52 | −0.4208 (3) | −0.1728 (3) | 0.9893 (2) | 0.0414 (10) | |
H52 | −0.4916 | −0.1979 | 0.9713 | 0.050* | |
C51 | −0.3337 (3) | −0.1737 (3) | 0.9438 (2) | 0.0416 (10) | |
H51 | −0.3468 | −0.2012 | 0.8951 | 0.050* | |
S5 | 0.33793 (8) | 0.44470 (8) | 0.03989 (5) | 0.0394 (3) | |
S6 | 0.44065 (9) | 0.41358 (8) | −0.10252 (5) | 0.0390 (3) | |
C67 | 0.4538 (3) | 0.4708 (3) | −0.0128 (2) | 0.0304 (8) | |
C68 | 0.3041 (4) | 0.3692 (3) | −0.0959 (2) | 0.0458 (10) | |
H68 | 0.2637 | 0.3362 | −0.1368 | 0.055* | |
C69 | 0.2573 (3) | 0.3823 (4) | −0.0323 (2) | 0.0464 (11) | |
H69 | 0.1828 | 0.3587 | −0.0262 | 0.056* | |
C34 | 0.4753 (3) | 0.3830 (3) | 0.39775 (19) | 0.0271 (8) | |
H34 | 0.4504 | 0.3160 | 0.4113 | 0.033* | |
N2 | 0.1384 (2) | 0.4173 (2) | 0.55352 (15) | 0.0245 (6) | |
N1 | 0.6065 (2) | 0.4933 (2) | 0.33453 (15) | 0.0233 (6) | |
C33 | 0.4212 (2) | 0.4643 (2) | 0.42080 (16) | 0.0175 (6) | |
C36 | 0.3232 (2) | 0.4474 (2) | 0.46646 (17) | 0.0194 (6) | |
C32 | 0.4630 (3) | 0.5598 (3) | 0.39829 (19) | 0.0265 (8) | |
H32 | 0.4286 | 0.6171 | 0.4117 | 0.032* | |
C31 | 0.5546 (3) | 0.5714 (3) | 0.35633 (19) | 0.0270 (8) | |
H31 | 0.5821 | 0.6375 | 0.3423 | 0.032* | |
C38 | 0.1810 (3) | 0.5093 (3) | 0.5347 (2) | 0.0363 (9) | |
H38 | 0.1472 | 0.5657 | 0.5515 | 0.044* | |
C40 | 0.2785 (3) | 0.3517 (3) | 0.4857 (2) | 0.0332 (9) | |
H40 | 0.3102 | 0.2937 | 0.4695 | 0.040* | |
C37 | 0.2715 (3) | 0.5281 (3) | 0.4922 (2) | 0.0324 (9) | |
H37 | 0.2981 | 0.5957 | 0.4807 | 0.039* | |
C39 | 0.1880 (3) | 0.3400 (3) | 0.5286 (2) | 0.0316 (8) | |
H39 | 0.1594 | 0.2732 | 0.5409 | 0.038* | |
C35 | 0.5659 (3) | 0.4019 (3) | 0.3548 (2) | 0.0294 (8) | |
H35 | 0.6010 | 0.3459 | 0.3391 | 0.035* | |
N3 | 0.5459 (2) | 0.2524 (2) | 0.18685 (16) | 0.0285 (7) | |
C43 | 0.7038 (3) | 0.2416 (3) | 0.0791 (2) | 0.0283 (8) | |
N4 | 0.9165 (3) | 0.2080 (2) | −0.1014 (2) | 0.0429 (9) | |
C50 | 0.8463 (3) | 0.1583 (3) | 0.0132 (2) | 0.0370 (9) | |
H50 | 0.8464 | 0.1130 | 0.0506 | 0.044* | |
C45 | 0.5883 (3) | 0.1676 (3) | 0.17096 (19) | 0.0291 (8) | |
H45 | 0.5640 | 0.1098 | 0.1971 | 0.035* | |
C44 | 0.6664 (3) | 0.1589 (3) | 0.11818 (19) | 0.0306 (8) | |
H44 | 0.6937 | 0.0964 | 0.1091 | 0.037* | |
C49 | 0.9123 (3) | 0.1497 (3) | −0.0458 (2) | 0.0384 (10) | |
H49 | 0.9578 | 0.0987 | −0.0467 | 0.046* | |
C46 | 0.7802 (3) | 0.2324 (3) | 0.0182 (2) | 0.0325 (8) | |
C41 | 0.5871 (3) | 0.3331 (3) | 0.1525 (2) | 0.0322 (8) | |
H41 | 0.5619 | 0.3958 | 0.1651 | 0.039* | |
C42 | 0.6650 (3) | 0.3319 (3) | 0.0990 (2) | 0.0328 (8) | |
H42 | 0.6914 | 0.3925 | 0.0764 | 0.039* | |
C47 | 0.7800 (3) | 0.2930 (3) | −0.0423 (2) | 0.0435 (10) | |
H47 | 0.7336 | 0.3432 | −0.0430 | 0.052* | |
C48 | 0.8479 (3) | 0.2785 (3) | −0.1003 (2) | 0.0439 (10) | |
H48 | 0.8464 | 0.3190 | −0.1405 | 0.053* | |
H11O | 0.395 (3) | 0.237 (3) | 0.235 (2) | 0.037 (12)* | |
H12O | 0.217 (3) | −0.119 (3) | 0.267 (2) | 0.043 (12)* | |
H5O | 0.020 (4) | 0.217 (3) | 0.826 (2) | 0.050 (13)* | |
H4O | −0.113 (4) | −0.128 (4) | 0.904 (3) | 0.061 (15)* | |
H13O | 0.015 (4) | −0.188 (4) | 0.366 (3) | 0.054 (15)* | |
H8O | −0.009 (4) | 0.623 (4) | 0.390 (3) | 0.063 (16)* | |
H9O | 0.377 (4) | 0.541 (4) | 0.225 (3) | 0.078 (17)* | |
H2O | −0.101 (6) | −0.443 (6) | 0.897 (4) | 0.15 (3)* | |
H6O | 0.214 (4) | 0.288 (3) | 0.734 (2) | 0.059 (14)* | |
H1O | 0.264 (4) | −0.531 (4) | 0.719 (3) | 0.055 (15)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0210 (4) | 0.0274 (4) | 0.0211 (4) | 0.0031 (3) | 0.0014 (3) | −0.0002 (3) |
S2 | 0.0222 (4) | 0.0341 (5) | 0.0202 (4) | −0.0010 (3) | 0.0060 (3) | −0.0006 (4) |
S3 | 0.0206 (4) | 0.0326 (5) | 0.0244 (4) | 0.0061 (3) | 0.0075 (3) | 0.0013 (4) |
S4 | 0.0241 (4) | 0.0261 (4) | 0.0264 (4) | 0.0016 (3) | −0.0011 (3) | 0.0006 (4) |
O7 | 0.0171 (11) | 0.0183 (11) | 0.0214 (11) | 0.0038 (8) | 0.0090 (9) | 0.0008 (9) |
O6 | 0.0258 (13) | 0.0223 (12) | 0.0391 (15) | 0.0076 (10) | 0.0176 (11) | 0.0089 (11) |
O14 | 0.0161 (10) | 0.0156 (10) | 0.0249 (12) | 0.0043 (8) | 0.0069 (9) | 0.0007 (9) |
O1 | 0.0241 (13) | 0.0220 (12) | 0.0400 (15) | 0.0046 (10) | 0.0167 (11) | 0.0042 (11) |
O13 | 0.0237 (12) | 0.0162 (11) | 0.0292 (13) | 0.0059 (9) | 0.0122 (10) | 0.0045 (10) |
O10 | 0.0197 (11) | 0.0239 (12) | 0.0290 (13) | 0.0059 (9) | 0.0126 (9) | 0.0039 (10) |
O8 | 0.0231 (12) | 0.0170 (11) | 0.0391 (15) | 0.0044 (9) | 0.0175 (11) | 0.0022 (11) |
O11 | 0.0194 (12) | 0.0209 (12) | 0.0303 (13) | 0.0056 (10) | 0.0127 (10) | 0.0036 (10) |
O9 | 0.0232 (12) | 0.0215 (12) | 0.0403 (15) | 0.0051 (10) | 0.0179 (11) | 0.0068 (11) |
O4 | 0.0264 (13) | 0.0203 (12) | 0.0331 (14) | 0.0068 (10) | 0.0198 (11) | 0.0020 (11) |
O12 | 0.0259 (13) | 0.0166 (11) | 0.0325 (13) | 0.0068 (9) | 0.0152 (10) | 0.0018 (10) |
O5 | 0.0242 (13) | 0.0214 (12) | 0.0446 (15) | 0.0093 (10) | 0.0210 (11) | 0.0057 (11) |
O2 | 0.0422 (16) | 0.0243 (14) | 0.063 (2) | 0.0073 (12) | 0.0391 (14) | 0.0131 (14) |
C8 | 0.0180 (15) | 0.0214 (16) | 0.0215 (16) | 0.0071 (12) | 0.0073 (12) | −0.0007 (13) |
O3 | 0.0319 (14) | 0.0252 (13) | 0.0475 (16) | 0.0059 (11) | 0.0305 (12) | 0.0067 (12) |
C6 | 0.0190 (16) | 0.0202 (16) | 0.0239 (17) | 0.0028 (12) | 0.0088 (13) | 0.0007 (14) |
C1 | 0.0154 (15) | 0.0191 (15) | 0.0195 (16) | 0.0011 (12) | 0.0038 (12) | 0.0013 (13) |
C22 | 0.0169 (15) | 0.0211 (16) | 0.0188 (15) | 0.0051 (12) | 0.0062 (12) | 0.0003 (13) |
C24 | 0.0163 (15) | 0.0184 (15) | 0.0199 (15) | 0.0073 (12) | 0.0040 (12) | 0.0011 (13) |
C14 | 0.0183 (16) | 0.0261 (17) | 0.0204 (16) | 0.0058 (13) | 0.0097 (12) | 0.0039 (14) |
C19 | 0.0215 (16) | 0.0140 (15) | 0.0284 (18) | 0.0028 (12) | 0.0081 (13) | −0.0008 (13) |
C18 | 0.0173 (15) | 0.0181 (15) | 0.0271 (17) | 0.0047 (12) | 0.0057 (13) | −0.0004 (14) |
C26 | 0.0177 (15) | 0.0217 (16) | 0.0169 (15) | 0.0060 (12) | 0.0050 (12) | 0.0023 (13) |
C64 | 0.0222 (16) | 0.0182 (15) | 0.0163 (15) | 0.0049 (12) | 0.0035 (12) | 0.0023 (13) |
C7 | 0.0180 (16) | 0.0228 (16) | 0.0246 (17) | 0.0043 (13) | 0.0080 (13) | 0.0008 (14) |
C25 | 0.0127 (14) | 0.0203 (16) | 0.0204 (15) | 0.0036 (12) | 0.0036 (11) | 0.0017 (13) |
C23 | 0.0184 (15) | 0.0193 (15) | 0.0191 (15) | 0.0070 (12) | 0.0056 (12) | 0.0021 (13) |
C28 | 0.0151 (14) | 0.0165 (15) | 0.0198 (15) | 0.0028 (12) | 0.0026 (12) | 0.0042 (13) |
C11 | 0.0135 (14) | 0.0239 (16) | 0.0185 (15) | 0.0054 (12) | 0.0073 (12) | 0.0018 (13) |
N5 | 0.0255 (15) | 0.0272 (15) | 0.0288 (16) | 0.0058 (12) | 0.0109 (12) | 0.0006 (13) |
C12 | 0.0201 (16) | 0.0218 (16) | 0.0220 (16) | 0.0071 (13) | 0.0082 (13) | 0.0027 (13) |
C16 | 0.0150 (15) | 0.0176 (15) | 0.0193 (15) | 0.0021 (12) | 0.0040 (12) | 0.0031 (13) |
C29 | 0.0149 (15) | 0.0203 (16) | 0.0236 (16) | 0.0054 (12) | 0.0086 (12) | 0.0020 (13) |
C63 | 0.0218 (16) | 0.0174 (16) | 0.0257 (17) | 0.0063 (12) | 0.0046 (13) | 0.0024 (14) |
C2 | 0.0175 (15) | 0.0227 (16) | 0.0213 (16) | 0.0023 (12) | 0.0071 (12) | 0.0002 (13) |
C27 | 0.0165 (15) | 0.0174 (15) | 0.0187 (15) | 0.0059 (12) | 0.0037 (12) | 0.0000 (13) |
C30 | 0.0180 (15) | 0.0178 (15) | 0.0227 (16) | 0.0071 (12) | 0.0060 (12) | 0.0019 (13) |
C9 | 0.0156 (15) | 0.0190 (15) | 0.0190 (15) | 0.0068 (12) | 0.0039 (12) | −0.0008 (13) |
C10 | 0.0159 (15) | 0.0224 (16) | 0.0174 (15) | 0.0030 (12) | 0.0047 (12) | 0.0030 (13) |
C17 | 0.0158 (15) | 0.0204 (16) | 0.0248 (17) | 0.0050 (12) | 0.0087 (12) | 0.0015 (13) |
C21 | 0.0151 (15) | 0.0214 (16) | 0.0213 (16) | 0.0050 (12) | 0.0040 (12) | 0.0012 (13) |
C3 | 0.0196 (16) | 0.0216 (16) | 0.0281 (18) | 0.0064 (13) | 0.0075 (13) | 0.0006 (14) |
C66 | 0.0187 (16) | 0.0299 (18) | 0.0304 (19) | 0.0030 (14) | 0.0067 (14) | 0.0074 (15) |
C15 | 0.0190 (16) | 0.0222 (16) | 0.0193 (16) | 0.0068 (13) | 0.0075 (12) | 0.0000 (13) |
N6 | 0.0248 (15) | 0.0372 (17) | 0.0280 (16) | 0.0096 (13) | 0.0106 (12) | −0.0003 (14) |
C20 | 0.0181 (16) | 0.0201 (16) | 0.0251 (17) | 0.0029 (12) | 0.0088 (13) | 0.0018 (14) |
C4 | 0.0237 (17) | 0.0197 (16) | 0.036 (2) | 0.0021 (13) | 0.0150 (14) | 0.0037 (15) |
C5 | 0.0241 (17) | 0.0232 (17) | 0.0318 (19) | 0.0018 (14) | 0.0146 (14) | 0.0054 (15) |
C13 | 0.0191 (16) | 0.0206 (16) | 0.0220 (16) | 0.0032 (12) | 0.0096 (12) | 0.0069 (13) |
C56 | 0.0167 (16) | 0.0305 (18) | 0.0251 (17) | 0.0018 (13) | 0.0068 (13) | −0.0033 (15) |
C53 | 0.0217 (17) | 0.0265 (17) | 0.0239 (17) | 0.0050 (13) | 0.0085 (13) | 0.0003 (14) |
C65 | 0.0191 (16) | 0.0244 (17) | 0.0311 (19) | 0.0045 (13) | 0.0005 (13) | 0.0048 (15) |
C62 | 0.0175 (17) | 0.0291 (19) | 0.050 (2) | 0.0032 (14) | 0.0022 (15) | 0.0020 (18) |
C57 | 0.0279 (19) | 0.035 (2) | 0.045 (2) | 0.0083 (16) | 0.0113 (17) | 0.0059 (18) |
C61 | 0.0193 (17) | 0.0317 (19) | 0.042 (2) | 0.0066 (14) | 0.0120 (15) | 0.0031 (17) |
C59 | 0.0256 (19) | 0.046 (2) | 0.048 (2) | 0.0081 (17) | 0.0077 (17) | 0.003 (2) |
C54 | 0.031 (2) | 0.048 (2) | 0.0237 (18) | 0.0117 (17) | 0.0080 (15) | 0.0053 (17) |
C58 | 0.034 (2) | 0.042 (2) | 0.035 (2) | 0.0052 (17) | 0.0162 (17) | 0.0051 (18) |
C55 | 0.0242 (19) | 0.052 (2) | 0.034 (2) | 0.0072 (17) | 0.0064 (15) | 0.0036 (19) |
C60 | 0.0269 (19) | 0.055 (3) | 0.034 (2) | 0.0091 (18) | 0.0070 (16) | 0.0094 (19) |
C52 | 0.0233 (19) | 0.066 (3) | 0.033 (2) | 0.0049 (18) | 0.0025 (15) | −0.008 (2) |
C51 | 0.033 (2) | 0.061 (3) | 0.028 (2) | 0.0069 (19) | 0.0068 (16) | −0.0090 (19) |
S5 | 0.0345 (5) | 0.0487 (6) | 0.0340 (5) | 0.0034 (4) | 0.0132 (4) | 0.0028 (5) |
S6 | 0.0474 (6) | 0.0351 (5) | 0.0324 (5) | 0.0007 (4) | 0.0147 (4) | 0.0006 (4) |
C67 | 0.034 (2) | 0.0262 (19) | 0.032 (2) | 0.0052 (15) | 0.0088 (15) | 0.0052 (16) |
C68 | 0.051 (3) | 0.051 (3) | 0.033 (2) | 0.001 (2) | 0.0051 (19) | 0.004 (2) |
C69 | 0.035 (2) | 0.058 (3) | 0.045 (2) | −0.002 (2) | 0.0050 (18) | 0.010 (2) |
C34 | 0.0243 (17) | 0.0222 (17) | 0.035 (2) | 0.0037 (14) | 0.0132 (15) | 0.0051 (15) |
N2 | 0.0213 (14) | 0.0238 (14) | 0.0284 (15) | 0.0032 (11) | 0.0100 (11) | 0.0022 (12) |
N1 | 0.0191 (14) | 0.0258 (15) | 0.0252 (15) | 0.0040 (11) | 0.0074 (11) | 0.0008 (12) |
C33 | 0.0154 (15) | 0.0201 (15) | 0.0172 (15) | 0.0037 (12) | 0.0029 (12) | −0.0001 (13) |
C36 | 0.0174 (15) | 0.0222 (16) | 0.0187 (16) | 0.0046 (12) | 0.0038 (12) | −0.0009 (13) |
C32 | 0.0237 (17) | 0.0207 (16) | 0.036 (2) | 0.0061 (13) | 0.0140 (15) | 0.0043 (15) |
C31 | 0.0247 (17) | 0.0204 (17) | 0.036 (2) | 0.0023 (14) | 0.0131 (15) | 0.0044 (15) |
C38 | 0.033 (2) | 0.0246 (18) | 0.054 (2) | 0.0114 (15) | 0.0281 (18) | 0.0042 (18) |
C40 | 0.0293 (19) | 0.0211 (17) | 0.051 (2) | 0.0081 (15) | 0.0226 (17) | 0.0064 (17) |
C37 | 0.032 (2) | 0.0210 (17) | 0.046 (2) | 0.0070 (15) | 0.0211 (17) | 0.0070 (17) |
C39 | 0.0289 (19) | 0.0234 (18) | 0.043 (2) | 0.0052 (15) | 0.0163 (16) | 0.0050 (16) |
C35 | 0.0276 (18) | 0.0252 (18) | 0.038 (2) | 0.0082 (14) | 0.0175 (15) | 0.0072 (16) |
N3 | 0.0268 (15) | 0.0280 (16) | 0.0319 (16) | 0.0082 (12) | 0.0086 (12) | 0.0022 (13) |
C43 | 0.0194 (17) | 0.0310 (19) | 0.035 (2) | 0.0062 (14) | 0.0078 (14) | −0.0023 (16) |
N4 | 0.0356 (19) | 0.0328 (18) | 0.060 (2) | 0.0056 (14) | 0.0280 (17) | −0.0024 (17) |
C50 | 0.034 (2) | 0.047 (2) | 0.033 (2) | 0.0186 (18) | 0.0074 (16) | −0.0008 (18) |
C45 | 0.0269 (18) | 0.035 (2) | 0.0283 (19) | 0.0108 (15) | 0.0061 (14) | 0.0092 (16) |
C44 | 0.0251 (18) | 0.040 (2) | 0.0304 (19) | 0.0168 (16) | 0.0042 (15) | 0.0009 (17) |
C49 | 0.026 (2) | 0.055 (3) | 0.037 (2) | 0.0225 (18) | 0.0066 (16) | −0.005 (2) |
C46 | 0.0235 (18) | 0.0283 (19) | 0.044 (2) | 0.0018 (15) | 0.0146 (16) | −0.0047 (17) |
C41 | 0.0296 (19) | 0.0284 (19) | 0.039 (2) | 0.0077 (15) | 0.0079 (16) | 0.0003 (17) |
C42 | 0.0278 (19) | 0.0305 (19) | 0.039 (2) | 0.0028 (15) | 0.0105 (16) | 0.0003 (17) |
C47 | 0.044 (2) | 0.029 (2) | 0.058 (3) | 0.0089 (18) | 0.025 (2) | 0.004 (2) |
C48 | 0.046 (2) | 0.032 (2) | 0.053 (3) | 0.0036 (18) | 0.022 (2) | 0.005 (2) |
S1—C65 | 1.742 (3) | C66—H66 | 0.9500 |
S1—C64 | 1.767 (3) | C15—H15 | 0.9500 |
S2—C66 | 1.754 (3) | N6—C58 | 1.328 (5) |
S2—C64 | 1.763 (3) | N6—C59 | 1.346 (5) |
S3—C61 | 1.749 (4) | C4—C5 | 1.380 (4) |
S3—C63 | 1.766 (3) | C4—H4 | 0.9500 |
S4—C62 | 1.747 (4) | C56—C57 | 1.377 (5) |
S4—C63 | 1.769 (3) | C56—C60 | 1.401 (5) |
O7—C1 | 1.373 (4) | C56—C53 | 1.495 (4) |
O7—C9 | 1.386 (3) | C53—C54 | 1.368 (5) |
O6—C13 | 1.371 (4) | C53—C52 | 1.381 (5) |
O6—H6O | 0.93 (5) | C65—H65 | 0.9500 |
O14—C16 | 1.372 (4) | C62—C61 | 1.320 (5) |
O14—C24 | 1.388 (3) | C62—H62 | 0.9500 |
O1—C3 | 1.360 (4) | C57—C58 | 1.390 (5) |
O1—H1O | 0.76 (5) | C57—H57 | 0.9500 |
O13—C28 | 1.365 (4) | C61—H61 | 0.9500 |
O13—H13O | 0.76 (5) | C59—C60 | 1.396 (5) |
O10—C22 | 1.256 (3) | C59—H59 | 0.9500 |
O8—C18 | 1.355 (4) | C54—C55 | 1.387 (5) |
O8—H8O | 0.76 (5) | C54—H54 | 0.9500 |
O11—C23 | 1.360 (4) | C58—H58 | 0.9500 |
O11—H11O | 0.80 (4) | C55—H55 | 0.9500 |
O9—C20 | 1.355 (4) | C60—H60 | 0.9500 |
O9—H9O | 0.93 (5) | C52—C51 | 1.383 (5) |
O4—C8 | 1.358 (4) | C52—H52 | 0.9500 |
O4—H4O | 0.83 (5) | C51—H51 | 0.9500 |
O12—C27 | 1.361 (4) | S5—C69 | 1.750 (5) |
O12—H12O | 0.88 (4) | S5—C67 | 1.758 (4) |
O5—C12 | 1.362 (4) | S6—C68 | 1.733 (4) |
O5—H5O | 0.87 (4) | S6—C67 | 1.769 (4) |
O2—C5 | 1.360 (4) | C67—C67i | 1.355 (7) |
O2—H2O | 0.81 (7) | C68—C69 | 1.328 (6) |
C8—C9 | 1.364 (4) | C68—H68 | 0.9500 |
C8—C7 | 1.447 (4) | C69—H69 | 0.9500 |
O3—C7 | 1.258 (4) | C34—C35 | 1.391 (4) |
C6—C1 | 1.403 (4) | C34—C33 | 1.403 (4) |
C6—C5 | 1.426 (4) | C34—H34 | 0.9500 |
C6—C7 | 1.434 (4) | N2—C38 | 1.330 (4) |
C1—C2 | 1.384 (4) | N2—C39 | 1.335 (4) |
C22—C21 | 1.437 (4) | N1—C35 | 1.325 (4) |
C22—C23 | 1.456 (4) | N1—C31 | 1.346 (4) |
C24—C23 | 1.370 (4) | C33—C32 | 1.391 (4) |
C24—C25 | 1.468 (4) | C33—C36 | 1.492 (4) |
C14—C15 | 1.384 (4) | C36—C40 | 1.383 (4) |
C14—C13 | 1.384 (4) | C36—C37 | 1.393 (4) |
C14—H14 | 0.9500 | C32—C31 | 1.384 (4) |
C19—C20 | 1.381 (4) | C32—H32 | 0.9500 |
C19—C18 | 1.405 (4) | C31—H31 | 0.9500 |
C19—H19 | 0.9500 | C38—C37 | 1.384 (5) |
C18—C17 | 1.392 (4) | C38—H38 | 0.9500 |
C26—C27 | 1.387 (4) | C40—C39 | 1.383 (5) |
C26—C25 | 1.410 (4) | C40—H40 | 0.9500 |
C26—H26 | 0.9500 | C37—H37 | 0.9500 |
C64—C63 | 1.346 (4) | C39—H39 | 0.9500 |
C25—C30 | 1.405 (4) | C35—H35 | 0.9500 |
C28—C29 | 1.387 (4) | N3—C41 | 1.325 (4) |
C28—C27 | 1.410 (4) | N3—C45 | 1.332 (4) |
C11—C12 | 1.383 (4) | C43—C44 | 1.384 (5) |
C11—C10 | 1.411 (4) | C43—C42 | 1.389 (5) |
C11—H11 | 0.9500 | C43—C46 | 1.492 (5) |
N5—C51 | 1.307 (5) | N4—C49 | 1.329 (5) |
N5—C55 | 1.336 (5) | N4—C48 | 1.367 (5) |
C12—C13 | 1.408 (4) | C50—C46 | 1.379 (5) |
C16—C17 | 1.380 (4) | C50—C49 | 1.381 (5) |
C16—C21 | 1.401 (4) | C50—H50 | 0.9500 |
C29—C30 | 1.387 (4) | C45—C44 | 1.396 (5) |
C29—H29 | 0.9500 | C45—H45 | 0.9500 |
C2—C3 | 1.394 (4) | C44—H44 | 0.9500 |
C2—H2 | 0.9500 | C49—H49 | 0.9500 |
C30—H30 | 0.9500 | C46—C47 | 1.427 (6) |
C9—C10 | 1.466 (4) | C41—C42 | 1.393 (5) |
C10—C15 | 1.402 (4) | C41—H41 | 0.9500 |
C17—H17 | 0.9500 | C42—H42 | 0.9500 |
C21—C20 | 1.429 (4) | C47—C48 | 1.393 (5) |
C3—C4 | 1.391 (4) | C47—H47 | 0.9500 |
C66—C65 | 1.322 (5) | C48—H48 | 0.9500 |
C65—S1—C64 | 94.35 (15) | C14—C13—C12 | 119.0 (3) |
C66—S2—C64 | 94.56 (15) | C57—C56—C60 | 118.0 (3) |
C61—S3—C63 | 94.55 (16) | C57—C56—C53 | 121.5 (3) |
C62—S4—C63 | 94.59 (17) | C60—C56—C53 | 120.3 (3) |
C1—O7—C9 | 120.9 (2) | C54—C53—C52 | 116.4 (3) |
C13—O6—H6O | 109 (3) | C54—C53—C56 | 121.1 (3) |
C16—O14—C24 | 121.7 (2) | C52—C53—C56 | 122.5 (3) |
C3—O1—H1O | 109 (4) | C66—C65—S1 | 118.8 (3) |
C28—O13—H13O | 113 (4) | C66—C65—H65 | 120.6 |
C18—O8—H8O | 106 (4) | S1—C65—H65 | 120.6 |
C23—O11—H11O | 113 (3) | C61—C62—S4 | 118.2 (3) |
C20—O9—H9O | 104 (3) | C61—C62—H62 | 120.9 |
C8—O4—H4O | 116 (3) | S4—C62—H62 | 120.9 |
C27—O12—H12O | 113 (3) | C56—C57—C58 | 119.1 (4) |
C12—O5—H5O | 115 (3) | C56—C57—H57 | 120.4 |
C5—O2—H2O | 103 (6) | C58—C57—H57 | 120.4 |
O4—C8—C9 | 120.1 (3) | C62—C61—S3 | 118.2 (3) |
O4—C8—C7 | 118.6 (3) | C62—C61—H61 | 120.9 |
C9—C8—C7 | 121.2 (3) | S3—C61—H61 | 120.9 |
C1—C6—C5 | 117.1 (3) | N6—C59—C60 | 123.3 (4) |
C1—C6—C7 | 120.5 (3) | N6—C59—H59 | 118.3 |
C5—C6—C7 | 122.4 (3) | C60—C59—H59 | 118.3 |
O7—C1—C2 | 117.2 (3) | C53—C54—C55 | 119.7 (3) |
O7—C1—C6 | 120.1 (3) | C53—C54—H54 | 120.1 |
C2—C1—C6 | 122.7 (3) | C55—C54—H54 | 120.1 |
O10—C22—C21 | 123.2 (3) | N6—C58—C57 | 124.1 (4) |
O10—C22—C23 | 120.2 (3) | N6—C58—H58 | 117.9 |
C21—C22—C23 | 116.6 (3) | C57—C58—H58 | 117.9 |
C23—C24—O14 | 120.0 (3) | N5—C55—C54 | 123.3 (4) |
C23—C24—C25 | 129.5 (3) | N5—C55—H55 | 118.3 |
O14—C24—C25 | 110.5 (2) | C54—C55—H55 | 118.3 |
C15—C14—C13 | 120.9 (3) | C59—C60—C56 | 118.5 (4) |
C15—C14—H14 | 119.6 | C59—C60—H60 | 120.7 |
C13—C14—H14 | 119.6 | C56—C60—H60 | 120.7 |
C20—C19—C18 | 119.6 (3) | C53—C52—C51 | 120.1 (4) |
C20—C19—H19 | 120.2 | C53—C52—H52 | 119.9 |
C18—C19—H19 | 120.2 | C51—C52—H52 | 119.9 |
O8—C18—C17 | 122.1 (3) | N5—C51—C52 | 123.5 (4) |
O8—C18—C19 | 116.6 (3) | N5—C51—H51 | 118.3 |
C17—C18—C19 | 121.3 (3) | C52—C51—H51 | 118.3 |
C27—C26—C25 | 120.5 (3) | C69—S5—C67 | 94.53 (19) |
C27—C26—H26 | 119.7 | C68—S6—C67 | 94.48 (19) |
C25—C26—H26 | 119.7 | C67i—C67—S5 | 123.2 (4) |
C63—C64—S2 | 122.3 (3) | C67i—C67—S6 | 122.4 (4) |
C63—C64—S1 | 123.0 (2) | S5—C67—S6 | 114.4 (2) |
S2—C64—S1 | 114.72 (17) | C69—C68—S6 | 118.5 (4) |
O3—C7—C6 | 123.2 (3) | C69—C68—H68 | 120.8 |
O3—C7—C8 | 120.4 (3) | S6—C68—H68 | 120.8 |
C6—C7—C8 | 116.3 (3) | C68—C69—S5 | 117.6 (3) |
C30—C25—C26 | 118.3 (3) | C68—C69—H69 | 121.2 |
C30—C25—C24 | 119.9 (3) | S5—C69—H69 | 121.2 |
C26—C25—C24 | 121.8 (3) | C35—C34—C33 | 119.1 (3) |
O11—C23—C24 | 121.2 (3) | C35—C34—H34 | 120.5 |
O11—C23—C22 | 117.6 (3) | C33—C34—H34 | 120.5 |
C24—C23—C22 | 121.2 (3) | C38—N2—C39 | 116.0 (3) |
O13—C28—C29 | 119.8 (3) | C35—N1—C31 | 117.0 (3) |
O13—C28—C27 | 120.9 (3) | C32—C33—C34 | 116.6 (3) |
C29—C28—C27 | 119.2 (3) | C32—C33—C36 | 122.5 (3) |
C12—C11—C10 | 121.3 (3) | C34—C33—C36 | 120.9 (3) |
C12—C11—H11 | 119.3 | C40—C36—C37 | 116.1 (3) |
C10—C11—H11 | 119.3 | C40—C36—C33 | 122.5 (3) |
C51—N5—C55 | 116.6 (3) | C37—C36—C33 | 121.4 (3) |
O5—C12—C11 | 124.5 (3) | C31—C32—C33 | 120.2 (3) |
O5—C12—C13 | 115.5 (3) | C31—C32—H32 | 119.9 |
C11—C12—C13 | 120.0 (3) | C33—C32—H32 | 119.9 |
O14—C16—C17 | 116.8 (3) | N1—C31—C32 | 123.0 (3) |
O14—C16—C21 | 120.4 (3) | N1—C31—H31 | 118.5 |
C17—C16—C21 | 122.7 (3) | C32—C31—H31 | 118.5 |
C28—C29—C30 | 120.6 (3) | N2—C38—C37 | 124.2 (3) |
C28—C29—H29 | 119.7 | N2—C38—H38 | 117.9 |
C30—C29—H29 | 119.7 | C37—C38—H38 | 117.9 |
C64—C63—S3 | 122.0 (3) | C39—C40—C36 | 120.3 (3) |
C64—C63—S4 | 123.6 (3) | C39—C40—H40 | 119.9 |
S3—C63—S4 | 114.42 (17) | C36—C40—H40 | 119.9 |
C1—C2—C3 | 118.2 (3) | C38—C37—C36 | 119.6 (3) |
C1—C2—H2 | 120.9 | C38—C37—H37 | 120.2 |
C3—C2—H2 | 120.9 | C36—C37—H37 | 120.2 |
O12—C27—C26 | 123.5 (3) | N2—C39—C40 | 123.7 (3) |
O12—C27—C28 | 116.1 (3) | N2—C39—H39 | 118.1 |
C26—C27—C28 | 120.4 (3) | C40—C39—H39 | 118.1 |
C29—C30—C25 | 121.0 (3) | N1—C35—C34 | 124.1 (3) |
C29—C30—H30 | 119.5 | N1—C35—H35 | 118.0 |
C25—C30—H30 | 119.5 | C34—C35—H35 | 118.0 |
C8—C9—O7 | 120.6 (3) | C41—N3—C45 | 116.0 (3) |
C8—C9—C10 | 128.8 (3) | C44—C43—C42 | 116.3 (3) |
O7—C9—C10 | 110.6 (2) | C44—C43—C46 | 121.1 (3) |
C15—C10—C11 | 117.5 (3) | C42—C43—C46 | 122.5 (3) |
C15—C10—C9 | 119.6 (3) | C49—N4—C48 | 116.9 (3) |
C11—C10—C9 | 122.9 (3) | C46—C50—C49 | 120.3 (4) |
C16—C17—C18 | 118.4 (3) | C46—C50—H50 | 119.8 |
C16—C17—H17 | 120.8 | C49—C50—H50 | 119.8 |
C18—C17—H17 | 120.8 | N3—C45—C44 | 123.8 (3) |
C16—C21—C20 | 117.6 (3) | N3—C45—H45 | 118.1 |
C16—C21—C22 | 120.1 (3) | C44—C45—H45 | 118.1 |
C20—C21—C22 | 122.3 (3) | C43—C44—C45 | 119.8 (3) |
O1—C3—C4 | 115.9 (3) | C43—C44—H44 | 120.1 |
O1—C3—C2 | 122.7 (3) | C45—C44—H44 | 120.1 |
C4—C3—C2 | 121.4 (3) | N4—C49—C50 | 124.4 (4) |
C65—C66—S2 | 117.6 (3) | N4—C49—H49 | 117.8 |
C65—C66—H66 | 121.2 | C50—C49—H49 | 117.8 |
S2—C66—H66 | 121.2 | C50—C46—C47 | 116.2 (3) |
C14—C15—C10 | 121.3 (3) | C50—C46—C43 | 122.3 (4) |
C14—C15—H15 | 119.4 | C47—C46—C43 | 121.1 (3) |
C10—C15—H15 | 119.4 | N3—C41—C42 | 124.3 (3) |
C58—N6—C59 | 116.8 (3) | N3—C41—H41 | 117.9 |
O9—C20—C19 | 119.5 (3) | C42—C41—H41 | 117.9 |
O9—C20—C21 | 120.0 (3) | C43—C42—C41 | 119.5 (3) |
C19—C20—C21 | 120.4 (3) | C43—C42—H42 | 120.2 |
C5—C4—C3 | 119.7 (3) | C41—C42—H42 | 120.2 |
C5—C4—H4 | 120.1 | C48—C47—C46 | 119.8 (4) |
C3—C4—H4 | 120.1 | C48—C47—H47 | 120.1 |
O2—C5—C4 | 120.3 (3) | C46—C47—H47 | 120.1 |
O2—C5—C6 | 118.9 (3) | N4—C48—C47 | 122.2 (4) |
C4—C5—C6 | 120.8 (3) | N4—C48—H48 | 118.9 |
O6—C13—C14 | 119.6 (3) | C47—C48—H48 | 118.9 |
O6—C13—C12 | 121.4 (3) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···S2 | 0.95 | 2.75 | 3.557 (3) | 144 |
C19—H19···O12ii | 0.95 | 2.48 | 3.367 (4) | 156 |
C26—H26···O11 | 0.95 | 2.27 | 2.907 (4) | 124 |
C11—H11···O4 | 0.95 | 2.22 | 2.862 (4) | 124 |
C4—H4···O5iii | 0.95 | 2.47 | 3.342 (4) | 153 |
C69—H69···O3iv | 0.95 | 2.61 | 3.152 (5) | 117 |
C34—H34···S1 | 0.95 | 2.97 | 3.905 (4) | 166 |
C37—H37···S4v | 0.95 | 2.93 | 3.847 (4) | 162 |
C41—H41···O10 | 0.95 | 2.47 | 3.102 (4) | 124 |
C41—H41···S6i | 0.95 | 2.87 | 3.626 (4) | 137 |
C48—H48···O2vi | 0.95 | 2.52 | 3.050 (5) | 116 |
O11—H11O···O10 | 0.80 (4) | 2.34 (4) | 2.721 (3) | 110 (3) |
O11—H11O···N3 | 0.80 (4) | 2.08 (4) | 2.841 (4) | 159 (4) |
O12—H12O···N6vii | 0.88 (4) | 1.83 (4) | 2.703 (3) | 175 (4) |
O5—H5O···N4viii | 0.87 (4) | 1.86 (5) | 2.732 (4) | 175 (4) |
O4—H4O···N5 | 0.83 (5) | 1.88 (5) | 2.680 (3) | 162 (5) |
O13—H13O···O8iii | 0.76 (5) | 2.17 (5) | 2.807 (3) | 143 (5) |
O13—H13O···O12 | 0.76 (5) | 2.34 (5) | 2.711 (3) | 112 (4) |
O8—H8O···N2ix | 0.76 (5) | 1.96 (5) | 2.693 (3) | 162 (5) |
O9—H9O···O10 | 0.93 (5) | 1.78 (5) | 2.638 (3) | 152 (5) |
O2—H2O···O3 | 0.81 (7) | 1.84 (8) | 2.608 (4) | 157 (8) |
O6—H6O···O1ii | 0.93 (5) | 2.03 (5) | 2.794 (3) | 139 (4) |
O6—H6O···O5 | 0.93 (5) | 2.22 (5) | 2.710 (3) | 112 (3) |
O1—H1O···N1x | 0.76 (5) | 1.92 (5) | 2.672 (3) | 167 (5) |
C14—H14···S2 | 0.95 | 2.75 | 3.557 (3) | 144 |
C19—H19···O12ii | 0.95 | 2.48 | 3.367 (4) | 156 |
C26—H26···O11 | 0.95 | 2.27 | 2.907 (4) | 124 |
C11—H11···O4 | 0.95 | 2.22 | 2.862 (4) | 124 |
C4—H4···O5iii | 0.95 | 2.47 | 3.342 (4) | 153 |
C69—H69···O3iv | 0.95 | 2.61 | 3.152 (5) | 117 |
C34—H34···S1 | 0.95 | 2.97 | 3.905 (4) | 166 |
C37—H37···S4v | 0.95 | 2.93 | 3.847 (4) | 162 |
C41—H41···O10 | 0.95 | 2.47 | 3.102 (4) | 124 |
C41—H41···S6i | 0.95 | 2.87 | 3.626 (4) | 137 |
C48—H48···O2vi | 0.95 | 2.52 | 3.050 (5) | 116 |
O11—H11O···O10 | 0.80 (4) | 2.34 (4) | 2.721 (3) | 110 (3) |
O11—H11O···N3 | 0.80 (4) | 2.08 (4) | 2.841 (4) | 159 (4) |
O12—H12O···N6vii | 0.88 (4) | 1.83 (4) | 2.703 (3) | 175 (4) |
O5—H5O···N4viii | 0.87 (4) | 1.86 (5) | 2.732 (4) | 175 (4) |
O4—H4O···N5 | 0.83 (5) | 1.88 (5) | 2.680 (3) | 162 (5) |
O13—H13O···O8iii | 0.76 (5) | 2.17 (5) | 2.807 (3) | 143 (5) |
O13—H13O···O12 | 0.76 (5) | 2.34 (5) | 2.711 (3) | 112 (4) |
O8—H8O···N2ix | 0.76 (5) | 1.96 (5) | 2.693 (3) | 162 (5) |
O9—H9O···O10 | 0.93 (5) | 1.78 (5) | 2.638 (3) | 152 (5) |
O2—H2O···O3 | 0.81 (7) | 1.84 (8) | 2.608 (4) | 157 (8) |
O6—H6O···O1ii | 0.93 (5) | 2.03 (5) | 2.794 (3) | 139 (4) |
O6—H6O···O5 | 0.93 (5) | 2.22 (5) | 2.710 (3) | 112 (3) |
O1—H1O···N1x | 0.76 (5) | 1.92 (5) | 2.672 (3) | 167 (5) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y+1, z; (iii) x, y−1, z; (iv) −x, −y, −z+1; (v) −x+1, −y+1, −z+1; (vi) x+1, y+1, z−1; (vii) x+1, y, z−1; (viii) x−1, y, z+1; (ix) −x, −y+1, −z+1; (x) −x+1, −y, −z+1. |
C30H20N2O7S | V = 1330.6 Å3 |
Mr = 552.54 | Z = 2 |
Triclinic, P1 | F(000) = 572 |
a = 9.974 Å | Dx = 1.379 Mg m−3 |
b = 11.421 Å | Mo Kα radiation, λ = 0.71073 Å |
c = 13.009 Å | µ = 0.17 mm−1 |
α = 78.51° | T = 150 K |
β = 85.22° | Plate, yellow |
γ = 66.39° | 0.75 × 0.20 × 0.10 mm |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | Rint = 0.060 |
Tmin = 0.732, Tmax = 1.000 | θmax = 27.5°, θmin = 3.0° |
14146 measured reflections | h = −12→12 |
6078 independent reflections | k = −14→14 |
3677 reflections with I > 2σ(I) | l = −16→16 |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.202 | w = 1/[σ2(Fo2) + (0.095P)2 + 0.4836P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.003 |
6078 reflections | Δρmax = 0.64 e Å−3 |
439 parameters | Δρmin = −0.25 e Å−3 |
C30H20N2O7S | γ = 66.39° |
Mr = 552.54 | V = 1330.6 Å3 |
Triclinic, P1 | Z = 2 |
a = 9.974 Å | Mo Kα radiation |
b = 11.421 Å | µ = 0.17 mm−1 |
c = 13.009 Å | T = 150 K |
α = 78.51° | 0.75 × 0.20 × 0.10 mm |
β = 85.22° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 6078 independent reflections |
Tmin = 0.732, Tmax = 1.000 | 3677 reflections with I > 2σ(I) |
14146 measured reflections | Rint = 0.060 |
R[F2 > 2σ(F2)] = 0.068 | 1 restraint |
wR(F2) = 0.202 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.64 e Å−3 |
6078 reflections | Δρmin = −0.25 e Å−3 |
439 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
H1O | 0.712 (4) | 0.313 (3) | 0.086 (3) | 0.050 (10)* | |
H4O | 0.109 (4) | 0.473 (3) | 0.571 (3) | 0.044 (10)* | |
H5O | 0.557 (4) | 0.328 (4) | 0.945 (3) | 0.070 (12)* | |
H6O | 0.881 (6) | 0.194 (5) | 0.879 (4) | 0.13 (2)* | |
H2O | 0.085 (4) | 0.496 (4) | 0.260 (3) | 0.061 (11)* | |
C1 | 0.4774 (3) | 0.3761 (3) | 0.33473 (19) | 0.0199 (6) | |
C2 | 0.5785 (3) | 0.3469 (3) | 0.2549 (2) | 0.0226 (6) | |
H2 | 0.6806 | 0.3123 | 0.2684 | 0.027* | |
C3 | 0.5260 (3) | 0.3701 (3) | 0.15367 (19) | 0.0213 (6) | |
C4 | 0.3762 (3) | 0.4196 (3) | 0.1337 (2) | 0.0236 (6) | |
H4 | 0.3427 | 0.4340 | 0.0643 | 0.028* | |
C5 | 0.2778 (3) | 0.4473 (3) | 0.2141 (2) | 0.0223 (6) | |
C6 | 0.3267 (3) | 0.4258 (3) | 0.3185 (2) | 0.0219 (6) | |
C7 | 0.2291 (3) | 0.4530 (3) | 0.4049 (2) | 0.0238 (6) | |
C8 | 0.2934 (3) | 0.4220 (3) | 0.5070 (2) | 0.0235 (6) | |
C9 | 0.4425 (3) | 0.3712 (3) | 0.51919 (19) | 0.0206 (6) | |
C10 | 0.5284 (3) | 0.3322 (3) | 0.61538 (19) | 0.0199 (6) | |
C11 | 0.4652 (3) | 0.3526 (3) | 0.71366 (19) | 0.0204 (6) | |
H11 | 0.3618 | 0.3930 | 0.7199 | 0.024* | |
C12 | 0.5514 (3) | 0.3144 (3) | 0.80186 (19) | 0.0208 (6) | |
C13 | 0.7039 (3) | 0.2561 (3) | 0.7941 (2) | 0.0221 (6) | |
C14 | 0.7663 (3) | 0.2359 (3) | 0.6967 (2) | 0.0255 (6) | |
H14 | 0.8698 | 0.1961 | 0.6905 | 0.031* | |
C15 | 0.6815 (3) | 0.2725 (3) | 0.6087 (2) | 0.0236 (6) | |
H15 | 0.7268 | 0.2572 | 0.5427 | 0.028* | |
C16 | 0.9790 (3) | 0.1592 (3) | 0.1788 (2) | 0.0353 (7) | |
H16 | 0.9278 | 0.1183 | 0.2277 | 0.042* | |
C17 | 1.1291 (3) | 0.1087 (3) | 0.1839 (2) | 0.0333 (7) | |
H17 | 1.1791 | 0.0345 | 0.2351 | 0.040* | |
C18 | 1.2080 (3) | 0.1670 (3) | 0.1135 (2) | 0.0277 (6) | |
C19 | 1.1259 (3) | 0.2757 (3) | 0.0413 (2) | 0.0313 (7) | |
H19 | 1.1737 | 0.3198 | −0.0077 | 0.038* | |
C20 | 0.9752 (3) | 0.3194 (3) | 0.0409 (2) | 0.0337 (7) | |
H20 | 0.9220 | 0.3928 | −0.0099 | 0.040* | |
C21 | 1.3686 (3) | 0.1183 (3) | 0.1088 (2) | 0.0304 (7) | |
C22 | 1.4586 (3) | 0.0130 (3) | 0.1713 (2) | 0.0326 (7) | |
C23 | 1.6187 (3) | −0.0339 (3) | 0.1638 (2) | 0.0299 (7) | |
C24 | 1.7060 (3) | −0.1393 (3) | 0.2362 (3) | 0.0354 (7) | |
H24 | 1.6621 | −0.1804 | 0.2912 | 0.042* | |
C25 | 1.8567 (3) | −0.1840 (3) | 0.2278 (3) | 0.0369 (8) | |
H25 | 1.9139 | −0.2564 | 0.2778 | 0.044* | |
C26 | 1.8417 (3) | −0.0278 (3) | 0.0841 (2) | 0.0325 (7) | |
H26 | 1.8883 | 0.0129 | 0.0310 | 0.039* | |
C27 | 1.6912 (3) | 0.0216 (3) | 0.0865 (2) | 0.0316 (7) | |
H27 | 1.6369 | 0.0938 | 0.0352 | 0.038* | |
C30 | 0.7069 (11) | −0.0486 (10) | 0.5021 (8) | 0.0415 (19) | 0.5401 |
C33 | 0.4539 (10) | 0.0066 (12) | 0.5048 (10) | 0.057 (3) | 0.4599 |
C34 | 0.9438 (14) | −0.0565 (13) | 0.4740 (9) | 0.099 (5) | 0.4634 |
H34 | 1.0294 | −0.0396 | 0.4556 | 0.119* | |
C37 | 0.712 (3) | −0.010 (2) | 0.4487 (15) | 0.128 (7) | 0.5366 |
C35 | 0.9457 (14) | −0.1689 (11) | 0.5499 (9) | 0.134 (5) | 0.5845 |
H35 | 1.0330 | −0.2339 | 0.5820 | 0.161* | |
C36 | 0.697 (2) | −0.110 (2) | 0.5691 (18) | 0.085 (5) | 0.4154 |
N1 | 0.9008 (2) | 0.2633 (3) | 0.10840 (19) | 0.0327 (6) | |
N2 | 1.9261 (3) | −0.1305 (2) | 0.1528 (2) | 0.0325 (6) | |
O1 | 0.6167 (2) | 0.3440 (2) | 0.07124 (14) | 0.0275 (5) | |
O2 | 0.1328 (2) | 0.4950 (2) | 0.19468 (15) | 0.0311 (5) | |
O3 | 0.09158 (19) | 0.5001 (2) | 0.39559 (14) | 0.0332 (5) | |
O4 | 0.2019 (2) | 0.4424 (2) | 0.59092 (15) | 0.0338 (5) | |
O5 | 0.4853 (2) | 0.3343 (2) | 0.89651 (14) | 0.0292 (5) | |
O6 | 0.7819 (2) | 0.2234 (2) | 0.88296 (14) | 0.0278 (5) | |
O7 | 0.53126 (18) | 0.35232 (18) | 0.43261 (13) | 0.0220 (4) | |
S1A | 0.8023 (9) | −0.1739 (7) | 0.5728 (5) | 0.090 (3) | 0.264 (6) |
S1B | 0.7971 (5) | 0.0316 (4) | 0.4265 (3) | 0.0550 (16) | 0.287 (5) |
S1C | 0.5490 (11) | 0.0598 (6) | 0.4205 (4) | 0.060 (3) | 0.257 (9) |
S1D | 0.4404 (15) | 0.0932 (7) | 0.4086 (5) | 0.062 (4) | 0.195 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0197 (13) | 0.0257 (14) | 0.0137 (12) | −0.0081 (11) | −0.0031 (10) | −0.0032 (10) |
C2 | 0.0136 (12) | 0.0285 (14) | 0.0222 (13) | −0.0036 (11) | −0.0007 (11) | −0.0064 (11) |
C3 | 0.0193 (13) | 0.0266 (14) | 0.0171 (12) | −0.0078 (11) | 0.0029 (10) | −0.0061 (11) |
C4 | 0.0213 (14) | 0.0306 (15) | 0.0178 (13) | −0.0079 (12) | −0.0035 (11) | −0.0051 (11) |
C5 | 0.0153 (13) | 0.0277 (14) | 0.0194 (13) | −0.0043 (11) | −0.0037 (10) | −0.0019 (11) |
C6 | 0.0170 (13) | 0.0281 (14) | 0.0176 (13) | −0.0067 (11) | 0.0008 (10) | −0.0026 (11) |
C7 | 0.0162 (13) | 0.0307 (15) | 0.0203 (13) | −0.0056 (11) | −0.0024 (11) | −0.0022 (11) |
C8 | 0.0181 (13) | 0.0339 (15) | 0.0160 (12) | −0.0080 (12) | 0.0014 (11) | −0.0042 (11) |
C9 | 0.0197 (13) | 0.0273 (14) | 0.0144 (12) | −0.0088 (11) | 0.0014 (10) | −0.0041 (11) |
C10 | 0.0178 (13) | 0.0257 (14) | 0.0161 (12) | −0.0082 (11) | −0.0031 (10) | −0.0025 (11) |
C11 | 0.0149 (12) | 0.0272 (14) | 0.0186 (12) | −0.0072 (11) | −0.0014 (10) | −0.0047 (11) |
C12 | 0.0193 (13) | 0.0276 (14) | 0.0157 (12) | −0.0098 (11) | 0.0039 (10) | −0.0044 (11) |
C13 | 0.0199 (13) | 0.0271 (14) | 0.0172 (13) | −0.0071 (11) | −0.0028 (11) | −0.0025 (11) |
C14 | 0.0138 (13) | 0.0340 (16) | 0.0235 (14) | −0.0034 (11) | 0.0017 (11) | −0.0069 (12) |
C15 | 0.0174 (13) | 0.0341 (15) | 0.0163 (12) | −0.0063 (12) | −0.0001 (10) | −0.0059 (11) |
C16 | 0.0224 (15) | 0.0472 (19) | 0.0335 (17) | −0.0124 (14) | 0.0015 (13) | −0.0048 (15) |
C17 | 0.0217 (15) | 0.0363 (17) | 0.0351 (17) | −0.0070 (13) | −0.0039 (13) | 0.0005 (14) |
C18 | 0.0195 (14) | 0.0289 (15) | 0.0337 (16) | −0.0062 (12) | −0.0020 (12) | −0.0096 (13) |
C19 | 0.0227 (15) | 0.0348 (17) | 0.0321 (16) | −0.0086 (13) | −0.0017 (12) | −0.0017 (13) |
C20 | 0.0236 (15) | 0.0391 (17) | 0.0302 (16) | −0.0038 (13) | −0.0043 (13) | −0.0046 (14) |
C21 | 0.0189 (14) | 0.0318 (16) | 0.0409 (17) | −0.0084 (12) | −0.0012 (13) | −0.0099 (13) |
C22 | 0.0188 (14) | 0.0331 (16) | 0.0437 (18) | −0.0064 (13) | −0.0041 (13) | −0.0082 (14) |
C23 | 0.0189 (14) | 0.0270 (15) | 0.0429 (17) | −0.0073 (12) | −0.0033 (13) | −0.0068 (13) |
C24 | 0.0211 (15) | 0.0318 (16) | 0.0474 (19) | −0.0087 (13) | −0.0029 (14) | 0.0034 (14) |
C25 | 0.0216 (15) | 0.0309 (16) | 0.052 (2) | −0.0042 (13) | −0.0091 (14) | −0.0023 (15) |
C26 | 0.0211 (15) | 0.0447 (18) | 0.0306 (16) | −0.0119 (13) | −0.0005 (12) | −0.0063 (14) |
C27 | 0.0213 (15) | 0.0352 (17) | 0.0334 (16) | −0.0060 (13) | −0.0047 (13) | −0.0045 (13) |
C30 | 0.052 (5) | 0.053 (5) | 0.032 (4) | −0.028 (4) | 0.017 (4) | −0.024 (4) |
C33 | 0.074 (9) | 0.060 (5) | 0.060 (6) | −0.035 (8) | 0.011 (8) | −0.051 (5) |
C34 | 0.120 (11) | 0.129 (11) | 0.094 (9) | −0.086 (10) | 0.077 (8) | −0.076 (8) |
C37 | 0.20 (2) | 0.136 (14) | 0.100 (13) | −0.102 (15) | 0.047 (13) | −0.074 (11) |
C35 | 0.124 (10) | 0.096 (8) | 0.124 (10) | 0.046 (7) | −0.050 (8) | −0.063 (8) |
C36 | 0.067 (11) | 0.096 (12) | 0.116 (15) | −0.027 (10) | −0.002 (10) | −0.080 (12) |
N1 | 0.0175 (12) | 0.0491 (16) | 0.0267 (13) | −0.0063 (11) | 0.0012 (10) | −0.0112 (12) |
N2 | 0.0194 (12) | 0.0384 (15) | 0.0355 (14) | −0.0063 (11) | −0.0033 (11) | −0.0073 (12) |
O1 | 0.0150 (10) | 0.0455 (12) | 0.0165 (9) | −0.0049 (9) | 0.0005 (8) | −0.0091 (9) |
O2 | 0.0132 (9) | 0.0531 (14) | 0.0192 (10) | −0.0055 (9) | −0.0013 (8) | −0.0049 (9) |
O3 | 0.0131 (10) | 0.0573 (14) | 0.0205 (10) | −0.0068 (9) | −0.0002 (8) | −0.0030 (9) |
O4 | 0.0141 (10) | 0.0610 (15) | 0.0171 (10) | −0.0062 (10) | 0.0005 (8) | −0.0052 (9) |
O5 | 0.0205 (10) | 0.0492 (13) | 0.0160 (9) | −0.0108 (9) | 0.0005 (8) | −0.0079 (9) |
O6 | 0.0186 (10) | 0.0411 (12) | 0.0170 (9) | −0.0047 (9) | −0.0051 (8) | −0.0035 (8) |
O7 | 0.0161 (9) | 0.0324 (10) | 0.0141 (9) | −0.0061 (8) | 0.0000 (7) | −0.0037 (8) |
S1A | 0.077 (5) | 0.097 (5) | 0.101 (4) | −0.038 (4) | −0.016 (4) | −0.013 (3) |
S1B | 0.054 (3) | 0.045 (2) | 0.059 (2) | −0.0094 (17) | 0.0056 (18) | −0.0149 (18) |
S1C | 0.079 (7) | 0.063 (3) | 0.049 (3) | −0.042 (4) | 0.009 (3) | −0.008 (2) |
S1D | 0.092 (12) | 0.051 (4) | 0.051 (3) | −0.035 (5) | −0.009 (4) | −0.008 (3) |
C1—O7 | 1.357 (3) | C26—C27 | 1.376 (4) |
C1—C2 | 1.379 (4) | C26—H26 | 0.9500 |
C1—C6 | 1.396 (3) | C27—H27 | 0.9500 |
C2—C3 | 1.395 (3) | C30—C37 | 0.757 (16) |
C2—H2 | 0.9500 | C30—C36 | 1.03 (2) |
C3—O1 | 1.344 (3) | C30—C33i | 1.484 (13) |
C3—C4 | 1.395 (4) | C30—S1A | 1.526 (12) |
C4—C5 | 1.367 (4) | C30—S1B | 1.664 (11) |
C4—H4 | 0.9500 | C30—S1C | 1.826 (14) |
C5—O2 | 1.351 (3) | C30—S1Di | 1.961 (17) |
C5—C6 | 1.422 (3) | C33—C33i | 0.872 (16) |
C6—C7 | 1.422 (4) | C33—S1Ci | 1.113 (15) |
C7—O3 | 1.263 (3) | C33—S1D | 1.411 (15) |
C7—C8 | 1.439 (3) | C33—C30i | 1.484 (13) |
C8—O4 | 1.358 (3) | C33—S1Di | 1.550 (18) |
C8—C9 | 1.373 (4) | C33—S1C | 1.580 (14) |
C9—O7 | 1.370 (3) | C33—C37i | 1.71 (2) |
C9—C10 | 1.466 (3) | C33—C36i | 1.72 (3) |
C10—C11 | 1.398 (3) | C34—C35 | 1.450 (15) |
C10—C15 | 1.404 (3) | C34—S1B | 1.503 (15) |
C11—C12 | 1.382 (3) | C34—H34 | 0.9500 |
C11—H11 | 0.9500 | C37—S1B | 1.11 (2) |
C12—O5 | 1.363 (3) | C37—S1C | 1.54 (3) |
C12—C13 | 1.399 (4) | C37—C33i | 1.71 (2) |
C13—O6 | 1.352 (3) | C37—C36 | 1.78 (2) |
C13—C14 | 1.384 (4) | C37—S1A | 2.15 (2) |
C14—C15 | 1.374 (3) | C35—S1A | 1.458 (16) |
C14—H14 | 0.9500 | C35—H35 | 0.9500 |
C15—H15 | 0.9500 | C36—S1A | 1.007 (16) |
C16—N1 | 1.343 (4) | C36—S1Di | 1.32 (2) |
C16—C17 | 1.374 (4) | C36—C33i | 1.72 (3) |
C16—H16 | 0.9500 | C36—S1Ci | 2.28 (2) |
C17—C18 | 1.400 (4) | O1—H1O | 0.90 (4) |
C17—H17 | 0.9500 | O2—H2O | 0.94 (4) |
C18—C19 | 1.393 (4) | O4—H4O | 0.89 (3) |
C18—C21 | 1.470 (4) | O5—H5O | 0.97 (4) |
C19—C20 | 1.381 (4) | O6—H6O | 0.91 (5) |
C19—H19 | 0.9500 | S1A—S1Di | 2.229 (16) |
C20—N1 | 1.335 (4) | S1B—S1C | 2.370 (11) |
C20—H20 | 0.9500 | S1C—S1D | 1.008 (9) |
C21—C22 | 1.335 (4) | S1C—C33i | 1.113 (15) |
C22—C23 | 1.469 (4) | S1C—C36i | 2.28 (2) |
C23—C27 | 1.388 (4) | S1C—S1Di | 2.520 (7) |
C23—C24 | 1.393 (4) | S1D—C36i | 1.32 (2) |
C24—C25 | 1.383 (4) | S1D—C33i | 1.550 (18) |
C24—H24 | 0.9500 | S1D—C30i | 1.961 (17) |
C25—N2 | 1.340 (4) | S1D—S1Ai | 2.229 (16) |
C25—H25 | 0.9500 | S1D—S1Ci | 2.520 (7) |
C26—N2 | 1.340 (4) | ||
O7—C1—C2 | 116.6 (2) | S1C—C33—C37i | 150.2 (13) |
O7—C1—C6 | 120.4 (2) | C33i—C33—C36i | 131 (2) |
C2—C1—C6 | 123.0 (2) | S1Ci—C33—C36i | 124.7 (12) |
C1—C2—C3 | 117.7 (2) | S1D—C33—C36i | 48.7 (11) |
C1—C2—H2 | 121.1 | C30i—C33—C36i | 36.6 (7) |
C3—C2—H2 | 121.1 | S1Di—C33—C36i | 165.1 (12) |
O1—C3—C2 | 121.8 (2) | S1C—C33—C36i | 87.6 (12) |
O1—C3—C4 | 117.0 (2) | C37i—C33—C36i | 62.7 (9) |
C2—C3—C4 | 121.3 (2) | C35—C34—S1B | 115.4 (9) |
C5—C4—C3 | 120.0 (2) | C35—C34—H34 | 122.3 |
C5—C4—H4 | 120.0 | S1B—C34—H34 | 122.3 |
C3—C4—H4 | 120.0 | C30—C37—S1B | 124 (3) |
O2—C5—C4 | 120.0 (2) | C30—C37—S1C | 100 (2) |
O2—C5—C6 | 119.5 (2) | S1B—C37—S1C | 125.7 (18) |
C4—C5—C6 | 120.5 (2) | C30—C37—C33i | 60.2 (19) |
C1—C6—C7 | 119.7 (2) | S1B—C37—C33i | 154.9 (15) |
C1—C6—C5 | 117.5 (2) | S1C—C37—C33i | 39.7 (8) |
C7—C6—C5 | 122.8 (2) | C30—C37—C36 | 4.7 (11) |
O3—C7—C6 | 123.0 (2) | S1B—C37—C36 | 127.6 (18) |
O3—C7—C8 | 119.9 (2) | S1C—C37—C36 | 98.6 (15) |
C6—C7—C8 | 117.1 (2) | C33i—C37—C36 | 59.0 (12) |
O4—C8—C9 | 121.1 (2) | C30—C37—S1A | 28.6 (17) |
O4—C8—C7 | 117.8 (2) | S1B—C37—S1A | 107.2 (16) |
C9—C8—C7 | 121.0 (2) | S1C—C37—S1A | 124.8 (14) |
O7—C9—C8 | 119.4 (2) | C33i—C37—S1A | 85.5 (11) |
O7—C9—C10 | 111.3 (2) | C36—C37—S1A | 27.8 (6) |
C8—C9—C10 | 129.3 (2) | C34—C35—S1A | 114.3 (9) |
C11—C10—C15 | 118.3 (2) | C34—C35—H35 | 122.8 |
C11—C10—C9 | 123.1 (2) | S1A—C35—H35 | 122.8 |
C15—C10—C9 | 118.7 (2) | S1A—C36—C30 | 97.0 (18) |
C12—C11—C10 | 120.7 (2) | S1A—C36—S1Di | 146 (2) |
C12—C11—H11 | 119.6 | C30—C36—S1Di | 112 (2) |
C10—C11—H11 | 119.6 | S1A—C36—C33i | 149.4 (19) |
O5—C12—C11 | 118.9 (2) | C30—C36—C33i | 59.2 (14) |
O5—C12—C13 | 120.6 (2) | S1Di—C36—C33i | 53.4 (9) |
C11—C12—C13 | 120.5 (2) | S1A—C36—C37 | 96.7 (18) |
O6—C13—C14 | 123.8 (2) | C30—C36—C37 | 3.4 (8) |
O6—C13—C12 | 117.5 (2) | S1Di—C36—C37 | 111.7 (18) |
C14—C13—C12 | 118.7 (2) | C33i—C36—C37 | 58.3 (12) |
C15—C14—C13 | 121.2 (2) | S1A—C36—S1Ci | 152.6 (17) |
C15—C14—H14 | 119.4 | C30—C36—S1Ci | 102.9 (16) |
C13—C14—H14 | 119.4 | S1Di—C36—S1Ci | 9.8 (6) |
C14—C15—C10 | 120.6 (2) | C33i—C36—S1Ci | 43.7 (6) |
C14—C15—H15 | 119.7 | C37—C36—S1Ci | 102.0 (14) |
C10—C15—H15 | 119.7 | C20—N1—C16 | 117.1 (2) |
N1—C16—C17 | 123.5 (3) | C25—N2—C26 | 116.6 (2) |
N1—C16—H16 | 118.2 | C3—O1—H1O | 115 (2) |
C17—C16—H16 | 118.2 | C5—O2—H2O | 107 (2) |
C16—C17—C18 | 119.8 (3) | C8—O4—H4O | 111 (2) |
C16—C17—H17 | 120.1 | C12—O5—H5O | 109 (2) |
C18—C17—H17 | 120.1 | C13—O6—H6O | 119 (3) |
C19—C18—C17 | 116.3 (2) | C1—O7—C9 | 122.27 (19) |
C19—C18—C21 | 119.2 (3) | C36—S1A—C35 | 137.1 (14) |
C17—C18—C21 | 124.5 (3) | C36—S1A—C30 | 42.1 (13) |
C20—C19—C18 | 120.2 (3) | C35—S1A—C30 | 100.1 (7) |
C20—C19—H19 | 119.9 | C36—S1A—C37 | 55.6 (15) |
C18—C19—H19 | 119.9 | C35—S1A—C37 | 88.9 (8) |
N1—C20—C19 | 123.1 (3) | C30—S1A—C37 | 13.7 (7) |
N1—C20—H20 | 118.4 | C36—S1A—S1Di | 19.2 (14) |
C19—C20—H20 | 118.4 | C35—S1A—S1Di | 156.1 (6) |
C22—C21—C18 | 124.6 (3) | C30—S1A—S1Di | 59.5 (6) |
C21—C22—C23 | 123.2 (3) | C37—S1A—S1Di | 72.3 (7) |
C27—C23—C24 | 116.6 (3) | C37—S1B—C34 | 112.6 (13) |
C27—C23—C22 | 123.3 (3) | C37—S1B—C30 | 22.1 (11) |
C24—C23—C22 | 120.1 (3) | C34—S1B—C30 | 94.6 (6) |
C25—C24—C23 | 119.8 (3) | C37—S1B—S1C | 31.8 (12) |
C25—C24—H24 | 120.1 | C34—S1B—S1C | 144.2 (5) |
C23—C24—H24 | 120.1 | C30—S1B—S1C | 50.2 (4) |
N2—C25—C24 | 123.4 (3) | S1D—S1C—C33i | 93.7 (8) |
N2—C25—H25 | 118.3 | S1D—S1C—C37 | 171.3 (10) |
C24—C25—H25 | 118.3 | C33i—S1C—C37 | 78.3 (11) |
N2—C26—C27 | 123.5 (3) | S1D—S1C—C33 | 61.5 (6) |
N2—C26—H26 | 118.2 | C33i—S1C—C33 | 32.3 (9) |
C27—C26—H26 | 118.2 | C37—S1C—C33 | 110.6 (11) |
C26—C27—C23 | 120.1 (3) | S1D—S1C—C30 | 148.1 (7) |
C26—C27—H27 | 119.9 | C33i—S1C—C30 | 54.3 (8) |
C23—C27—H27 | 119.9 | C37—S1C—C30 | 24.1 (7) |
C37—C30—C36 | 171.9 (19) | C33—S1C—C30 | 86.6 (7) |
C37—C30—C33i | 94 (2) | S1D—S1C—C36i | 12.9 (8) |
C36—C30—C33i | 84.2 (15) | C33i—S1C—C36i | 81.0 (10) |
C37—C30—S1A | 138 (2) | C37—S1C—C36i | 159.3 (8) |
C36—C30—S1A | 40.9 (10) | C33—S1C—C36i | 48.7 (9) |
C33i—C30—S1A | 122.3 (11) | C30—S1C—C36i | 135.3 (6) |
C37—C30—S1B | 33.6 (19) | S1D—S1C—S1B | 166.3 (6) |
C36—C30—S1B | 151.7 (13) | C33i—S1C—S1B | 98.2 (8) |
C33i—C30—S1B | 122.2 (9) | C37—S1C—S1B | 22.4 (8) |
S1A—C30—S1B | 115.3 (7) | C33—S1C—S1B | 130.0 (7) |
C37—C30—S1C | 56 (2) | C30—S1C—S1B | 44.4 (4) |
C36—C30—S1C | 121.7 (14) | C36i—S1C—S1B | 171.1 (4) |
C33i—C30—S1C | 37.5 (6) | S1D—S1C—S1Di | 97.5 (6) |
S1A—C30—S1C | 156.1 (7) | C33i—S1C—S1Di | 3.8 (5) |
S1B—C30—S1C | 85.4 (6) | C37—S1C—S1Di | 74.7 (10) |
C37—C30—S1Di | 139 (2) | C33—S1C—S1Di | 36.0 (5) |
C36—C30—S1Di | 38.5 (12) | C30—S1C—S1Di | 50.6 (6) |
C33i—C30—S1Di | 45.8 (7) | C36i—S1C—S1Di | 84.7 (9) |
S1A—C30—S1Di | 78.4 (7) | S1B—S1C—S1Di | 94.4 (6) |
S1B—C30—S1Di | 163.8 (7) | S1C—S1D—C36i | 157.3 (13) |
S1C—C30—S1Di | 83.4 (5) | S1C—S1D—C33 | 79.6 (7) |
C33i—C33—S1Ci | 105 (2) | C36i—S1D—C33 | 77.9 (13) |
C33i—C33—S1D | 82 (2) | S1C—S1D—C33i | 45.8 (5) |
S1Ci—C33—S1D | 173.3 (9) | C36i—S1D—C33i | 111.7 (13) |
C33i—C33—C30i | 167 (3) | C33—S1D—C33i | 33.8 (6) |
S1Ci—C33—C30i | 88.1 (9) | S1C—S1D—C30i | 128.5 (6) |
S1D—C33—C30i | 85.2 (11) | C36i—S1D—C30i | 29.0 (11) |
C33i—C33—S1Di | 64.3 (18) | C33—S1D—C30i | 48.9 (5) |
S1Ci—C33—S1Di | 40.5 (6) | C33i—S1D—C30i | 82.8 (5) |
S1D—C33—S1Di | 146.2 (6) | S1C—S1D—S1Ai | 164.4 (6) |
C30i—C33—S1Di | 128.6 (11) | C36i—S1D—S1Ai | 14.6 (10) |
C33i—C33—S1C | 42.9 (16) | C33—S1D—S1Ai | 89.9 (7) |
S1Ci—C33—S1C | 147.7 (9) | C33i—S1D—S1Ai | 123.1 (6) |
S1D—C33—S1C | 38.9 (5) | C30i—S1D—S1Ai | 42.1 (4) |
C30i—C33—S1C | 124.1 (12) | S1C—S1D—S1Ci | 82.5 (6) |
S1Di—C33—S1C | 107.3 (6) | C36i—S1D—S1Ci | 75.0 (13) |
C33i—C33—C37i | 167 (3) | C33—S1D—S1Ci | 3.0 (4) |
S1Ci—C33—C37i | 62.0 (11) | C33i—S1D—S1Ci | 36.8 (4) |
S1D—C33—C37i | 111.4 (13) | C30i—S1D—S1Ci | 46.0 (4) |
C30i—C33—C37i | 26.3 (7) | S1Ai—S1D—S1Ci | 87.1 (5) |
S1Di—C33—C37i | 102.4 (12) |
Symmetry code: (i) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4 | 0.95 | 2.24 | 2.896 (3) | 125 |
C16—H16···S1B | 0.95 | 2.97 | 3.882 (6) | 162 |
C20—H20···O2ii | 0.95 | 2.48 | 3.343 (4) | 151 |
C26—H26···O6iii | 0.95 | 2.66 | 3.367 (4) | 132 |
Symmetry codes: (ii) −x+1, −y+1, −z; (iii) x+1, y, z−1. |
C90H63N6O14 | V = 3440.5 Å3 |
Mr = 1452.46 | Z = 2 |
Triclinic, P1 | F(000) = 1514 |
a = 12.664 Å | Dx = 1.402 Mg m−3 |
b = 13.235 Å | Mo Kα radiation, λ = 0.71073 Å |
c = 22.191 Å | µ = 0.10 mm−1 |
α = 104.03° | T = 150 K |
β = 96.59° | Plate, yellow |
γ = 104.04° | 0.30 × 0.20 × 0.10 mm |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | Rint = 0.096 |
Tmin = 0.724, Tmax = 1.000 | θmax = 27.5°, θmin = 3.1° |
35694 measured reflections | h = −16→16 |
15699 independent reflections | k = −17→17 |
7254 reflections with I > 2σ(I) | l = −28→28 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.213 | w = 1/[σ2(Fo2) + (0.0849P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
15699 reflections | Δρmax = 0.68 e Å−3 |
1037 parameters | Δρmin = −0.67 e Å−3 |
C90H63N6O14 | γ = 104.04° |
Mr = 1452.46 | V = 3440.5 Å3 |
Triclinic, P1 | Z = 2 |
a = 12.664 Å | Mo Kα radiation |
b = 13.235 Å | µ = 0.10 mm−1 |
c = 22.191 Å | T = 150 K |
α = 104.03° | 0.30 × 0.20 × 0.10 mm |
β = 96.59° |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | 15699 independent reflections |
Tmin = 0.724, Tmax = 1.000 | 7254 reflections with I > 2σ(I) |
35694 measured reflections | Rint = 0.096 |
R[F2 > 2σ(F2)] = 0.080 | 0 restraints |
wR(F2) = 0.213 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.68 e Å−3 |
15699 reflections | Δρmin = −0.67 e Å−3 |
1037 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C72 | 0.2960 (3) | 0.4648 (3) | 0.00372 (19) | 0.0477 (10)* | |
H72 | 0.2256 | 0.4546 | 0.0159 | 0.057* | |
C68 | 0.6979 (3) | 0.5416 (3) | 0.05715 (19) | 0.0467 (10)* | |
H68 | 0.7638 | 0.5573 | 0.0871 | 0.056* | |
H37 | 0.424 (3) | 0.387 (3) | 0.4304 (16) | 0.051 (11)* | |
H48 | 0.735 (3) | 0.097 (3) | 0.1070 (17) | 0.059 (12)* | |
H49 | 0.715 (3) | 0.302 (2) | 0.0786 (14) | 0.029 (9)* | |
H8O | −0.043 (3) | 0.592 (3) | 0.4042 (18) | 0.049 (12)* | |
H9O | 0.301 (3) | 0.474 (3) | 0.2524 (17) | 0.051 (12)* | |
H36 | 0.403 (4) | 0.593 (3) | 0.415 (2) | 0.085 (16)* | |
H2O | 1.117 (4) | 0.449 (4) | 0.090 (2) | 0.104 (18)* | |
H6O | 0.823 (3) | −0.256 (3) | 0.2242 (19) | 0.067 (14)* | |
H4O | 1.151 (4) | 0.158 (4) | 0.091 (2) | 0.102 (18)* | |
H12O | 0.126 (4) | −0.175 (4) | 0.268 (2) | 0.096 (16)* | |
H11O | 0.318 (5) | 0.192 (4) | 0.263 (3) | 0.12 (2)* | |
H5O | 0.950 (4) | −0.204 (4) | 0.114 (2) | 0.094 (17)* | |
H1O | 0.797 (4) | 0.577 (3) | 0.263 (2) | 0.083 (16)* | |
H13O | −0.022 (4) | −0.245 (4) | 0.371 (2) | 0.098 (18)* | |
O7 | 0.91738 (18) | 0.26591 (16) | 0.20916 (10) | 0.0258 (5) | |
O4 | 1.0928 (2) | 0.13725 (18) | 0.11818 (12) | 0.0351 (6) | |
O1 | 0.8457 (2) | 0.60651 (18) | 0.23633 (11) | 0.0322 (6) | |
O3 | 1.1323 (2) | 0.33135 (18) | 0.09261 (11) | 0.0358 (6) | |
O6 | 0.7933 (2) | −0.2005 (2) | 0.24281 (12) | 0.0405 (7) | |
O5 | 0.9180 (2) | −0.20211 (18) | 0.15121 (12) | 0.0388 (7) | |
O2 | 1.0967 (2) | 0.5189 (2) | 0.10596 (12) | 0.0384 (6) | |
C9 | 0.9664 (3) | 0.1880 (2) | 0.18186 (15) | 0.0243 (7) | |
C2 | 0.8785 (3) | 0.4330 (3) | 0.22365 (15) | 0.0263 (8) | |
H2 | 0.8272 | 0.4126 | 0.2496 | 0.032* | |
C10 | 0.9235 (3) | 0.0865 (3) | 0.19773 (15) | 0.0252 (7) | |
C7 | 1.0666 (3) | 0.3139 (3) | 0.12974 (15) | 0.0282 (8) | |
C6 | 1.0109 (3) | 0.3902 (2) | 0.15735 (15) | 0.0249 (7) | |
C13 | 0.8364 (3) | −0.1067 (3) | 0.22755 (16) | 0.0289 (8) | |
C1 | 0.9368 (3) | 0.3641 (2) | 0.19682 (15) | 0.0251 (8) | |
C8 | 1.0416 (3) | 0.2108 (3) | 0.14438 (15) | 0.0281 (8) | |
C4 | 0.9718 (3) | 0.5641 (3) | 0.17219 (15) | 0.0300 (8) | |
H4 | 0.9836 | 0.6332 | 0.1646 | 0.036* | |
C11 | 0.9438 (3) | −0.0098 (3) | 0.16656 (15) | 0.0279 (8) | |
H11 | 0.9881 | −0.0094 | 0.1348 | 0.034* | |
C12 | 0.9009 (3) | −0.1057 (3) | 0.18079 (15) | 0.0273 (8) | |
C14 | 0.8143 (3) | −0.0126 (3) | 0.25776 (16) | 0.0306 (8) | |
H14 | 0.7691 | −0.0136 | 0.2891 | 0.037* | |
C3 | 0.8975 (3) | 0.5336 (3) | 0.21149 (15) | 0.0261 (8) | |
C15 | 0.8565 (3) | 0.0834 (3) | 0.24340 (16) | 0.0287 (8) | |
H15 | 0.8399 | 0.1476 | 0.2647 | 0.034* | |
C5 | 1.0266 (3) | 0.4930 (3) | 0.14518 (15) | 0.0287 (8) | |
O8 | −0.0016 (2) | 0.61531 (19) | 0.37832 (12) | 0.0361 (6) | |
O11 | 0.2687 (2) | 0.15626 (19) | 0.27997 (12) | 0.0333 (6) | |
O14 | 0.06809 (18) | 0.27392 (16) | 0.35320 (10) | 0.0266 (5) | |
O10 | 0.3123 (2) | 0.35139 (18) | 0.25436 (11) | 0.0360 (6) | |
O12 | 0.0698 (2) | −0.18951 (17) | 0.30045 (11) | 0.0339 (6) | |
O13 | −0.0423 (2) | −0.1838 (2) | 0.39704 (12) | 0.0402 (7) | |
O9 | 0.2743 (2) | 0.5382 (2) | 0.26521 (12) | 0.0379 (6) | |
C22 | 0.2352 (3) | 0.3290 (3) | 0.28517 (15) | 0.0259 (8) | |
C21 | 0.1740 (3) | 0.4024 (2) | 0.30770 (15) | 0.0246 (7) | |
C23 | 0.2089 (3) | 0.2267 (3) | 0.29956 (15) | 0.0247 (7) | |
C19 | 0.1356 (3) | 0.5763 (3) | 0.32186 (16) | 0.0311 (8) | |
H19 | 0.1505 | 0.6465 | 0.3156 | 0.037* | |
C24 | 0.1273 (3) | 0.2016 (3) | 0.33287 (15) | 0.0250 (7) | |
C25 | 0.0869 (3) | 0.1017 (2) | 0.35086 (15) | 0.0241 (7) | |
N4 | 0.9643 (2) | 0.2009 (2) | −0.05406 (14) | 0.0358 (7) | |
C27 | 0.0599 (3) | −0.0913 (3) | 0.33222 (15) | 0.0267 (8) | |
C16 | 0.0916 (3) | 0.3731 (2) | 0.34175 (15) | 0.0256 (8) | |
C17 | 0.0300 (3) | 0.4415 (2) | 0.36601 (15) | 0.0267 (8) | |
H17 | −0.0263 | 0.4193 | 0.3888 | 0.032* | |
C26 | 0.1029 (3) | 0.0043 (3) | 0.31767 (15) | 0.0254 (7) | |
H26 | 0.1440 | 0.0037 | 0.2845 | 0.030* | |
C30 | 0.0278 (3) | 0.1006 (3) | 0.39988 (15) | 0.0289 (8) | |
H30 | 0.0161 | 0.1662 | 0.4231 | 0.035* | |
C18 | 0.0531 (3) | 0.5429 (3) | 0.35602 (16) | 0.0293 (8) | |
C52 | 0.9291 (3) | 0.1229 (3) | −0.02611 (17) | 0.0362 (9) | |
H52 | 0.9555 | 0.0605 | −0.0353 | 0.043* | |
C20 | 0.1940 (3) | 0.5065 (3) | 0.29788 (16) | 0.0284 (8) | |
C51 | 0.8560 (3) | 0.1295 (3) | 0.01544 (16) | 0.0326 (8) | |
H51 | 0.8339 | 0.0726 | 0.0345 | 0.039* | |
C29 | −0.0144 (3) | 0.0053 (3) | 0.41524 (16) | 0.0310 (8) | |
H29 | −0.0539 | 0.0059 | 0.4491 | 0.037* | |
N3 | 0.4657 (3) | 0.1930 (2) | 0.22988 (14) | 0.0401 (8) | |
C28 | 0.0009 (3) | −0.0899 (3) | 0.38156 (16) | 0.0287 (8) | |
C49 | 0.7375 (3) | 0.2320 (3) | 0.07313 (17) | 0.0331 (9) | |
C45 | 0.6250 (3) | 0.1801 (3) | 0.15173 (16) | 0.0323 (8) | |
C50 | 0.8147 (3) | 0.2185 (3) | 0.02949 (15) | 0.0304 (8) | |
C48 | 0.7032 (3) | 0.1663 (3) | 0.10793 (16) | 0.0334 (9) | |
C43 | 0.5132 (3) | 0.1122 (3) | 0.22110 (16) | 0.0371 (9) | |
H43 | 0.4922 | 0.0584 | 0.2424 | 0.045* | |
C44 | 0.5909 (3) | 0.1022 (3) | 0.18289 (16) | 0.0358 (9) | |
H44 | 0.6209 | 0.0421 | 0.1779 | 0.043* | |
C54 | 0.8529 (3) | 0.2991 (3) | 0.00071 (16) | 0.0366 (9) | |
H54 | 0.8282 | 0.3625 | 0.0091 | 0.044* | |
C53 | 0.9264 (3) | 0.2876 (3) | −0.03983 (17) | 0.0401 (10) | |
H53 | 0.9513 | 0.3443 | −0.0586 | 0.048* | |
C46 | 0.5790 (3) | 0.2661 (3) | 0.16236 (18) | 0.0409 (10) | |
H46 | 0.6015 | 0.3233 | 0.1436 | 0.049* | |
C47 | 0.5000 (3) | 0.2684 (3) | 0.20048 (18) | 0.0433 (10) | |
H47 | 0.4683 | 0.3273 | 0.2061 | 0.052* | |
N1 | 0.7018 (2) | 0.5533 (2) | 0.30844 (13) | 0.0313 (7) | |
N2 | 0.1331 (2) | 0.4277 (2) | 0.54080 (13) | 0.0334 (7) | |
C36 | 0.4332 (3) | 0.5286 (3) | 0.40918 (16) | 0.0324 (9) | |
C38 | 0.3042 (3) | 0.4466 (3) | 0.47138 (15) | 0.0284 (8) | |
C32 | 0.5788 (3) | 0.4533 (3) | 0.36100 (16) | 0.0358 (9) | |
H32 | 0.5563 | 0.3900 | 0.3746 | 0.043* | |
C35 | 0.6496 (3) | 0.6302 (3) | 0.32030 (17) | 0.0356 (9) | |
H35 | 0.6740 | 0.6926 | 0.3061 | 0.043* | |
C37 | 0.3947 (3) | 0.4515 (3) | 0.43540 (16) | 0.0313 (8) | |
C33 | 0.5247 (3) | 0.5334 (3) | 0.37335 (16) | 0.0301 (8) | |
C39 | 0.2504 (3) | 0.5264 (3) | 0.48437 (16) | 0.0335 (9) | |
H39 | 0.2711 | 0.5892 | 0.4700 | 0.040* | |
C41 | 0.1856 (3) | 0.3512 (3) | 0.52799 (16) | 0.0330 (9) | |
H41 | 0.1640 | 0.2898 | 0.5435 | 0.040* | |
C42 | 0.2696 (3) | 0.3567 (3) | 0.49344 (16) | 0.0322 (8) | |
H42 | 0.3035 | 0.2994 | 0.4848 | 0.039* | |
C31 | 0.6653 (3) | 0.4666 (3) | 0.32887 (17) | 0.0365 (9) | |
H31 | 0.7011 | 0.4108 | 0.3207 | 0.044* | |
C34 | 0.5624 (3) | 0.6236 (3) | 0.35213 (17) | 0.0359 (9) | |
H34 | 0.5280 | 0.6806 | 0.3596 | 0.043* | |
C40 | 0.1660 (3) | 0.5134 (3) | 0.51861 (16) | 0.0363 (9) | |
H40 | 0.1291 | 0.5685 | 0.5269 | 0.044* | |
N5 | 0.2103 (3) | 0.8224 (2) | 0.21614 (15) | 0.0426 (8) | |
N6 | 0.7524 (3) | 0.8407 (2) | −0.04139 (15) | 0.0401 (8) | |
C65 | 0.7566 (3) | 0.8043 (3) | 0.00896 (19) | 0.0460 (10) | |
H65 | 0.8175 | 0.7776 | 0.0193 | 0.055* | |
C58 | 0.3109 (5) | 0.8868 (4) | 0.1421 (2) | 0.0739 (17) | |
H58 | 0.3220 | 0.9348 | 0.1163 | 0.089* | |
C62 | 0.5871 (3) | 0.8407 (4) | 0.0325 (2) | 0.0602 (14) | |
C55 | 0.2706 (4) | 0.7541 (3) | 0.2141 (2) | 0.0572 (13) | |
H55 | 0.2568 | 0.7047 | 0.2389 | 0.069* | |
C64 | 0.6650 (4) | 0.8748 (3) | −0.0547 (2) | 0.0523 (11) | |
H64 | 0.6584 | 0.8993 | −0.0914 | 0.063* | |
C59 | 0.2303 (4) | 0.8888 (3) | 0.18050 (19) | 0.0533 (12) | |
H59 | 0.1887 | 0.9397 | 0.1808 | 0.064* | |
C66 | 0.6779 (4) | 0.8026 (3) | 0.0477 (2) | 0.0541 (12) | |
H66 | 0.6854 | 0.7761 | 0.0837 | 0.065* | |
C60 | 0.4664 (6) | 0.8094 (5) | 0.1042 (3) | 0.151 (4) | |
C56 | 0.3520 (4) | 0.7490 (4) | 0.1786 (2) | 0.0689 (15) | |
H56 | 0.3928 | 0.6979 | 0.1803 | 0.083* | |
C61 | 0.4977 (5) | 0.8423 (6) | 0.0694 (3) | 0.127 (3) | |
C57 | 0.3747 (5) | 0.8147 (4) | 0.1418 (2) | 0.0747 (17) | |
C63 | 0.5841 (4) | 0.8773 (4) | −0.0198 (2) | 0.0688 (15) | |
H63 | 0.5249 | 0.9048 | −0.0319 | 0.083* | |
C93 | 0.4869 (3) | 0.8602 (3) | 0.48052 (18) | 0.0369 (9) | |
C80 | 0.4653 (4) | 0.8725 (3) | 0.41862 (19) | 0.0446 (10) | |
C89 | 0.4195 (3) | 0.8279 (3) | 0.57593 (18) | 0.0390 (9) | |
C76 | 0.5978 (3) | 0.8747 (3) | 0.51029 (19) | 0.0414 (10) | |
C92 | 0.3988 (3) | 0.8363 (3) | 0.51379 (17) | 0.0374 (9) | |
C91 | 0.6159 (3) | 0.8654 (3) | 0.57330 (19) | 0.0417 (10) | |
H91 | 0.6894 | 0.8758 | 0.5938 | 0.050* | |
C83 | 0.2714 (4) | 0.8362 (3) | 0.4232 (2) | 0.0521 (12) | |
H83 | 0.1981 | 0.8285 | 0.4035 | 0.063* | |
C90 | 0.5323 (3) | 0.8426 (3) | 0.60448 (18) | 0.0408 (10) | |
H90 | 0.5478 | 0.8359 | 0.6460 | 0.049* | |
C87 | 0.2244 (4) | 0.7978 (3) | 0.5798 (2) | 0.0524 (11) | |
H87 | 0.1656 | 0.7859 | 0.6025 | 0.063* | |
C88 | 0.3318 (4) | 0.8076 (3) | 0.6079 (2) | 0.0482 (11) | |
H88 | 0.3454 | 0.8004 | 0.6495 | 0.058* | |
C78 | 0.6606 (4) | 0.9099 (3) | 0.4164 (2) | 0.0597 (13) | |
H78 | 0.7195 | 0.9256 | 0.3942 | 0.072* | |
C82 | 0.3536 (4) | 0.8581 (3) | 0.3914 (2) | 0.0535 (12) | |
H82 | 0.3370 | 0.8642 | 0.3498 | 0.064* | |
C84 | 0.2885 (3) | 0.8239 (3) | 0.48470 (19) | 0.0423 (10) | |
C86 | 0.2035 (3) | 0.8053 (3) | 0.5194 (2) | 0.0493 (11) | |
H86 | 0.1297 | 0.7977 | 0.5005 | 0.059* | |
C77 | 0.6837 (4) | 0.9000 (3) | 0.4773 (2) | 0.0493 (11) | |
H77 | 0.7580 | 0.9105 | 0.4964 | 0.059* | |
C79 | 0.5541 (4) | 0.8975 (3) | 0.3878 (2) | 0.0560 (12) | |
H79 | 0.5409 | 0.9059 | 0.3466 | 0.067* | |
C69 | 0.5932 (3) | 0.5249 (3) | 0.07733 (18) | 0.0364 (9) | |
C70 | 0.4964 (3) | 0.5031 (3) | 0.03185 (16) | 0.0315 (8) | |
C71 | 0.3922 (3) | 0.4862 (3) | 0.05060 (17) | 0.0377 (9) | |
C73 | 0.3871 (3) | 0.4916 (3) | 0.11384 (19) | 0.0495 (11) | |
H73 | 0.3172 | 0.4786 | 0.1267 | 0.059* | |
C75 | 0.5842 (3) | 0.5326 (3) | 0.13992 (18) | 0.0422 (10) | |
H75 | 0.6494 | 0.5499 | 0.1706 | 0.051* | |
C74 | 0.4832 (3) | 0.5158 (3) | 0.15835 (19) | 0.0462 (10) | |
H74 | 0.4788 | 0.5205 | 0.2014 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O7 | 0.0285 (13) | 0.0224 (11) | 0.0305 (13) | 0.0080 (10) | 0.0125 (10) | 0.0108 (10) |
O4 | 0.0412 (16) | 0.0298 (13) | 0.0472 (16) | 0.0192 (12) | 0.0259 (13) | 0.0170 (12) |
O1 | 0.0361 (15) | 0.0277 (13) | 0.0410 (15) | 0.0149 (12) | 0.0170 (12) | 0.0139 (11) |
O3 | 0.0435 (16) | 0.0326 (13) | 0.0434 (15) | 0.0155 (12) | 0.0253 (13) | 0.0199 (12) |
O6 | 0.0517 (18) | 0.0281 (13) | 0.0550 (17) | 0.0155 (13) | 0.0302 (14) | 0.0224 (13) |
O5 | 0.0586 (18) | 0.0265 (13) | 0.0427 (16) | 0.0197 (13) | 0.0269 (14) | 0.0145 (12) |
O2 | 0.0475 (17) | 0.0353 (14) | 0.0480 (16) | 0.0179 (13) | 0.0309 (13) | 0.0239 (13) |
C9 | 0.0255 (19) | 0.0222 (16) | 0.0258 (18) | 0.0084 (15) | 0.0049 (15) | 0.0061 (14) |
C2 | 0.0251 (19) | 0.0294 (18) | 0.0289 (18) | 0.0096 (16) | 0.0104 (15) | 0.0121 (15) |
C10 | 0.0249 (19) | 0.0268 (17) | 0.0270 (18) | 0.0087 (15) | 0.0067 (15) | 0.0108 (15) |
C7 | 0.032 (2) | 0.0285 (18) | 0.0265 (18) | 0.0063 (16) | 0.0137 (16) | 0.0102 (15) |
C6 | 0.0269 (19) | 0.0246 (17) | 0.0246 (17) | 0.0064 (15) | 0.0063 (15) | 0.0097 (14) |
C13 | 0.029 (2) | 0.0299 (18) | 0.033 (2) | 0.0086 (16) | 0.0102 (16) | 0.0173 (16) |
C1 | 0.0265 (19) | 0.0226 (17) | 0.0254 (18) | 0.0024 (15) | 0.0043 (15) | 0.0099 (14) |
C8 | 0.033 (2) | 0.0251 (17) | 0.0290 (19) | 0.0103 (16) | 0.0104 (16) | 0.0084 (15) |
C4 | 0.034 (2) | 0.0260 (18) | 0.035 (2) | 0.0102 (17) | 0.0133 (17) | 0.0119 (16) |
C11 | 0.030 (2) | 0.0289 (18) | 0.0292 (19) | 0.0116 (16) | 0.0125 (16) | 0.0103 (15) |
C12 | 0.034 (2) | 0.0247 (17) | 0.0278 (18) | 0.0118 (16) | 0.0091 (16) | 0.0109 (15) |
C14 | 0.031 (2) | 0.0319 (19) | 0.034 (2) | 0.0116 (17) | 0.0202 (16) | 0.0110 (16) |
C3 | 0.030 (2) | 0.0234 (17) | 0.0278 (18) | 0.0084 (16) | 0.0103 (15) | 0.0092 (14) |
C15 | 0.033 (2) | 0.0233 (17) | 0.0335 (19) | 0.0121 (16) | 0.0121 (16) | 0.0084 (15) |
C5 | 0.032 (2) | 0.0285 (18) | 0.0287 (18) | 0.0058 (16) | 0.0135 (16) | 0.0123 (15) |
O8 | 0.0450 (16) | 0.0280 (13) | 0.0483 (16) | 0.0190 (12) | 0.0288 (14) | 0.0163 (12) |
O11 | 0.0326 (15) | 0.0311 (13) | 0.0471 (16) | 0.0162 (12) | 0.0187 (13) | 0.0186 (12) |
O14 | 0.0282 (13) | 0.0240 (12) | 0.0333 (13) | 0.0099 (11) | 0.0136 (11) | 0.0121 (10) |
O10 | 0.0387 (15) | 0.0344 (13) | 0.0449 (15) | 0.0134 (12) | 0.0240 (13) | 0.0185 (12) |
O12 | 0.0396 (15) | 0.0255 (13) | 0.0418 (15) | 0.0114 (12) | 0.0190 (13) | 0.0114 (11) |
O13 | 0.0508 (18) | 0.0295 (14) | 0.0544 (17) | 0.0164 (13) | 0.0303 (14) | 0.0228 (13) |
O9 | 0.0401 (16) | 0.0321 (14) | 0.0543 (17) | 0.0137 (13) | 0.0297 (13) | 0.0227 (13) |
C22 | 0.0230 (19) | 0.0309 (18) | 0.0266 (18) | 0.0080 (16) | 0.0061 (15) | 0.0121 (15) |
C21 | 0.0265 (19) | 0.0221 (16) | 0.0273 (18) | 0.0053 (15) | 0.0074 (15) | 0.0111 (14) |
C23 | 0.0222 (18) | 0.0263 (17) | 0.0284 (18) | 0.0092 (15) | 0.0090 (15) | 0.0087 (15) |
C19 | 0.034 (2) | 0.0251 (17) | 0.036 (2) | 0.0054 (16) | 0.0132 (17) | 0.0120 (16) |
C24 | 0.0227 (18) | 0.0246 (17) | 0.0283 (18) | 0.0088 (15) | 0.0052 (15) | 0.0060 (14) |
C25 | 0.0204 (18) | 0.0267 (17) | 0.0278 (18) | 0.0062 (15) | 0.0070 (15) | 0.0115 (15) |
N4 | 0.0395 (19) | 0.0366 (17) | 0.0392 (18) | 0.0161 (15) | 0.0195 (15) | 0.0139 (14) |
C27 | 0.0263 (19) | 0.0264 (18) | 0.0301 (19) | 0.0111 (16) | 0.0080 (15) | 0.0079 (15) |
C16 | 0.028 (2) | 0.0237 (17) | 0.0267 (18) | 0.0070 (16) | 0.0046 (15) | 0.0110 (15) |
C17 | 0.0257 (19) | 0.0259 (17) | 0.0306 (19) | 0.0072 (15) | 0.0105 (15) | 0.0095 (15) |
C26 | 0.0235 (18) | 0.0300 (18) | 0.0261 (18) | 0.0084 (16) | 0.0086 (15) | 0.0117 (15) |
C30 | 0.033 (2) | 0.0296 (18) | 0.0299 (19) | 0.0123 (16) | 0.0111 (16) | 0.0126 (15) |
C18 | 0.037 (2) | 0.0257 (18) | 0.0320 (19) | 0.0131 (17) | 0.0143 (17) | 0.0130 (15) |
C52 | 0.043 (2) | 0.033 (2) | 0.039 (2) | 0.0180 (19) | 0.0158 (18) | 0.0122 (17) |
C20 | 0.0254 (19) | 0.0251 (17) | 0.0324 (19) | 0.0032 (16) | 0.0078 (16) | 0.0068 (15) |
C51 | 0.034 (2) | 0.034 (2) | 0.032 (2) | 0.0095 (18) | 0.0127 (17) | 0.0106 (16) |
C29 | 0.033 (2) | 0.0320 (19) | 0.035 (2) | 0.0130 (17) | 0.0161 (17) | 0.0151 (16) |
N3 | 0.041 (2) | 0.0359 (18) | 0.0440 (19) | 0.0089 (16) | 0.0200 (16) | 0.0079 (15) |
C28 | 0.029 (2) | 0.0292 (18) | 0.036 (2) | 0.0121 (16) | 0.0123 (16) | 0.0172 (16) |
C49 | 0.034 (2) | 0.032 (2) | 0.034 (2) | 0.0116 (18) | 0.0114 (17) | 0.0042 (17) |
C45 | 0.029 (2) | 0.036 (2) | 0.0291 (19) | 0.0089 (17) | 0.0073 (16) | 0.0039 (16) |
C50 | 0.031 (2) | 0.036 (2) | 0.0249 (18) | 0.0111 (17) | 0.0093 (16) | 0.0061 (16) |
C48 | 0.027 (2) | 0.039 (2) | 0.031 (2) | 0.0096 (18) | 0.0051 (16) | 0.0038 (17) |
C43 | 0.037 (2) | 0.038 (2) | 0.037 (2) | 0.0062 (19) | 0.0146 (18) | 0.0119 (17) |
C44 | 0.034 (2) | 0.038 (2) | 0.036 (2) | 0.0113 (18) | 0.0088 (17) | 0.0095 (17) |
C54 | 0.048 (2) | 0.033 (2) | 0.038 (2) | 0.0218 (19) | 0.0162 (19) | 0.0118 (17) |
C53 | 0.051 (3) | 0.035 (2) | 0.045 (2) | 0.017 (2) | 0.024 (2) | 0.0192 (18) |
C46 | 0.043 (2) | 0.036 (2) | 0.046 (2) | 0.0103 (19) | 0.024 (2) | 0.0102 (18) |
C47 | 0.051 (3) | 0.036 (2) | 0.051 (2) | 0.017 (2) | 0.027 (2) | 0.0146 (19) |
N1 | 0.0292 (17) | 0.0304 (16) | 0.0376 (17) | 0.0081 (14) | 0.0164 (14) | 0.0110 (14) |
N2 | 0.0355 (18) | 0.0321 (16) | 0.0355 (17) | 0.0087 (15) | 0.0167 (14) | 0.0111 (14) |
C36 | 0.031 (2) | 0.035 (2) | 0.032 (2) | 0.0091 (18) | 0.0119 (17) | 0.0080 (17) |
C38 | 0.0252 (19) | 0.0334 (19) | 0.0250 (18) | 0.0059 (16) | 0.0096 (15) | 0.0055 (15) |
C32 | 0.037 (2) | 0.031 (2) | 0.040 (2) | 0.0050 (18) | 0.0169 (18) | 0.0114 (17) |
C35 | 0.041 (2) | 0.035 (2) | 0.042 (2) | 0.0153 (19) | 0.0231 (19) | 0.0194 (17) |
C37 | 0.032 (2) | 0.034 (2) | 0.030 (2) | 0.0109 (18) | 0.0104 (17) | 0.0086 (17) |
C33 | 0.028 (2) | 0.0308 (19) | 0.0291 (19) | 0.0059 (17) | 0.0085 (16) | 0.0036 (15) |
C39 | 0.043 (2) | 0.0313 (19) | 0.031 (2) | 0.0101 (18) | 0.0137 (18) | 0.0143 (16) |
C41 | 0.041 (2) | 0.0264 (18) | 0.033 (2) | 0.0073 (17) | 0.0134 (17) | 0.0106 (16) |
C42 | 0.035 (2) | 0.0293 (19) | 0.037 (2) | 0.0136 (17) | 0.0173 (17) | 0.0099 (16) |
C31 | 0.042 (2) | 0.0274 (19) | 0.044 (2) | 0.0108 (18) | 0.0187 (19) | 0.0114 (17) |
C34 | 0.040 (2) | 0.0314 (19) | 0.044 (2) | 0.0154 (18) | 0.0204 (19) | 0.0137 (17) |
C40 | 0.042 (2) | 0.038 (2) | 0.036 (2) | 0.0173 (19) | 0.0179 (18) | 0.0132 (17) |
N5 | 0.051 (2) | 0.0333 (17) | 0.044 (2) | 0.0089 (16) | 0.0238 (17) | 0.0093 (15) |
N6 | 0.042 (2) | 0.0370 (18) | 0.050 (2) | 0.0162 (16) | 0.0217 (17) | 0.0164 (16) |
C65 | 0.041 (2) | 0.053 (2) | 0.056 (3) | 0.021 (2) | 0.024 (2) | 0.022 (2) |
C58 | 0.105 (4) | 0.060 (3) | 0.035 (3) | −0.023 (3) | 0.021 (3) | 0.017 (2) |
C62 | 0.031 (3) | 0.066 (3) | 0.058 (3) | −0.001 (2) | 0.017 (2) | −0.020 (2) |
C55 | 0.077 (3) | 0.044 (2) | 0.071 (3) | 0.030 (2) | 0.048 (3) | 0.026 (2) |
C64 | 0.050 (3) | 0.050 (3) | 0.054 (3) | 0.018 (2) | 0.009 (2) | 0.005 (2) |
C59 | 0.073 (3) | 0.045 (2) | 0.041 (2) | 0.011 (2) | 0.013 (2) | 0.014 (2) |
C66 | 0.056 (3) | 0.061 (3) | 0.046 (3) | 0.008 (2) | 0.025 (2) | 0.018 (2) |
C60 | 0.133 (6) | 0.126 (5) | 0.088 (4) | −0.093 (5) | 0.085 (5) | −0.066 (4) |
C56 | 0.066 (3) | 0.054 (3) | 0.090 (4) | 0.020 (3) | 0.049 (3) | 0.007 (3) |
C61 | 0.063 (4) | 0.145 (6) | 0.084 (4) | −0.051 (4) | 0.050 (3) | −0.067 (4) |
C57 | 0.082 (4) | 0.052 (3) | 0.064 (3) | −0.014 (3) | 0.042 (3) | −0.012 (3) |
C63 | 0.047 (3) | 0.087 (4) | 0.064 (3) | 0.033 (3) | 0.004 (3) | −0.008 (3) |
C93 | 0.043 (2) | 0.0214 (18) | 0.041 (2) | 0.0113 (18) | 0.0035 (19) | −0.0004 (16) |
C80 | 0.062 (3) | 0.0235 (19) | 0.043 (2) | 0.013 (2) | 0.003 (2) | 0.0028 (17) |
C89 | 0.043 (2) | 0.0266 (19) | 0.047 (2) | 0.0142 (18) | 0.009 (2) | 0.0051 (17) |
C76 | 0.051 (3) | 0.0228 (18) | 0.048 (2) | 0.0110 (19) | 0.010 (2) | 0.0040 (17) |
C92 | 0.042 (2) | 0.0236 (18) | 0.040 (2) | 0.0116 (18) | −0.0013 (19) | −0.0007 (16) |
C91 | 0.037 (2) | 0.034 (2) | 0.051 (3) | 0.0120 (19) | −0.001 (2) | 0.0076 (19) |
C83 | 0.057 (3) | 0.040 (2) | 0.050 (3) | 0.018 (2) | −0.013 (2) | 0.002 (2) |
C90 | 0.046 (3) | 0.038 (2) | 0.039 (2) | 0.017 (2) | 0.002 (2) | 0.0094 (18) |
C87 | 0.051 (3) | 0.040 (2) | 0.067 (3) | 0.017 (2) | 0.014 (2) | 0.011 (2) |
C88 | 0.057 (3) | 0.039 (2) | 0.049 (3) | 0.018 (2) | 0.013 (2) | 0.008 (2) |
C78 | 0.085 (4) | 0.032 (2) | 0.063 (3) | 0.012 (3) | 0.031 (3) | 0.011 (2) |
C82 | 0.080 (4) | 0.038 (2) | 0.037 (2) | 0.021 (2) | −0.009 (2) | 0.0044 (19) |
C84 | 0.046 (3) | 0.029 (2) | 0.046 (2) | 0.015 (2) | −0.004 (2) | 0.0018 (18) |
C86 | 0.038 (2) | 0.040 (2) | 0.067 (3) | 0.016 (2) | 0.003 (2) | 0.006 (2) |
C77 | 0.048 (3) | 0.033 (2) | 0.064 (3) | 0.008 (2) | 0.015 (2) | 0.008 (2) |
C79 | 0.083 (4) | 0.034 (2) | 0.051 (3) | 0.017 (3) | 0.013 (3) | 0.010 (2) |
C69 | 0.031 (2) | 0.037 (2) | 0.044 (2) | 0.0102 (18) | 0.0089 (18) | 0.0137 (18) |
C70 | 0.029 (2) | 0.0287 (18) | 0.038 (2) | 0.0092 (17) | 0.0090 (17) | 0.0099 (17) |
C71 | 0.034 (2) | 0.044 (2) | 0.036 (2) | 0.0111 (19) | 0.0088 (18) | 0.0101 (18) |
C73 | 0.036 (2) | 0.065 (3) | 0.049 (3) | 0.009 (2) | 0.016 (2) | 0.018 (2) |
C75 | 0.044 (3) | 0.043 (2) | 0.038 (2) | 0.013 (2) | 0.0083 (19) | 0.0093 (19) |
C74 | 0.048 (3) | 0.054 (3) | 0.039 (2) | 0.012 (2) | 0.014 (2) | 0.017 (2) |
C72—C68i | 1.345 (5) | C54—C53 | 1.375 (5) |
C72—C71 | 1.430 (5) | C54—H54 | 0.9500 |
C72—H72 | 0.9500 | C53—H53 | 0.9500 |
C68—C72i | 1.345 (5) | C46—C47 | 1.383 (5) |
C68—C69 | 1.431 (5) | C46—H46 | 0.9500 |
C68—H68 | 0.9500 | C47—H47 | 0.9500 |
O7—C1 | 1.362 (4) | N1—C31 | 1.334 (4) |
O7—C9 | 1.381 (4) | N1—C35 | 1.335 (4) |
O4—C8 | 1.351 (4) | N2—C41 | 1.333 (4) |
O4—H4O | 1.02 (5) | N2—C40 | 1.339 (4) |
O1—C3 | 1.340 (4) | C36—C37 | 1.315 (5) |
O1—H1O | 0.99 (4) | C36—C33 | 1.476 (5) |
O3—C7 | 1.258 (4) | C36—H36 | 1.00 (4) |
O6—C13 | 1.368 (4) | C38—C39 | 1.382 (5) |
O6—H6O | 0.94 (4) | C38—C42 | 1.388 (4) |
O5—C12 | 1.366 (4) | C38—C37 | 1.468 (5) |
O5—H5O | 0.97 (5) | C32—C31 | 1.373 (5) |
O2—C5 | 1.356 (4) | C32—C33 | 1.386 (5) |
O2—H2O | 1.01 (5) | C32—H32 | 0.9500 |
C9—C8 | 1.362 (4) | C35—C34 | 1.375 (5) |
C9—C10 | 1.464 (4) | C35—H35 | 0.9500 |
C2—C1 | 1.377 (4) | C37—H37 | 1.00 (4) |
C2—C3 | 1.393 (4) | C33—C34 | 1.387 (5) |
C2—H2 | 0.9500 | C39—C40 | 1.382 (5) |
C10—C11 | 1.393 (4) | C39—H39 | 0.9500 |
C10—C15 | 1.396 (4) | C41—C42 | 1.379 (5) |
C7—C6 | 1.428 (4) | C41—H41 | 0.9500 |
C7—C8 | 1.448 (4) | C42—H42 | 0.9500 |
C6—C1 | 1.395 (4) | C31—H31 | 0.9500 |
C6—C5 | 1.422 (4) | C34—H34 | 0.9500 |
C13—C14 | 1.373 (4) | C40—H40 | 0.9500 |
C13—C12 | 1.393 (4) | N5—C55 | 1.314 (5) |
C4—C5 | 1.366 (4) | N5—C59 | 1.317 (5) |
C4—C3 | 1.408 (4) | N6—C65 | 1.320 (5) |
C4—H4 | 0.9500 | N6—C64 | 1.321 (5) |
C11—C12 | 1.380 (4) | C65—C66 | 1.389 (5) |
C11—H11 | 0.9500 | C65—H65 | 0.9500 |
C14—C15 | 1.382 (4) | C58—C57 | 1.392 (7) |
C14—H14 | 0.9500 | C58—C59 | 1.404 (6) |
C15—H15 | 0.9500 | C58—H58 | 0.9500 |
O8—C18 | 1.347 (4) | C62—C63 | 1.362 (6) |
O8—H8O | 0.88 (4) | C62—C66 | 1.403 (6) |
O11—C23 | 1.361 (4) | C62—C61 | 1.471 (6) |
O11—H11O | 0.87 (5) | C55—C56 | 1.371 (5) |
O14—C16 | 1.365 (4) | C55—H55 | 0.9500 |
O14—C24 | 1.378 (4) | C64—C63 | 1.355 (6) |
O10—C22 | 1.273 (4) | C64—H64 | 0.9500 |
O12—C27 | 1.363 (4) | C59—H59 | 0.9500 |
O12—H12O | 1.09 (5) | C66—H66 | 0.9500 |
O13—C28 | 1.372 (4) | C60—C61 | 1.046 (9) |
O13—H13O | 0.98 (5) | C60—C57 | 1.510 (7) |
O9—C20 | 1.359 (4) | C56—C57 | 1.336 (7) |
O9—H9O | 0.98 (4) | C56—H56 | 0.9500 |
C22—C21 | 1.419 (4) | C63—H63 | 0.9500 |
C22—C23 | 1.436 (4) | C93—C92 | 1.421 (5) |
C21—C16 | 1.391 (4) | C93—C80 | 1.425 (5) |
C21—C20 | 1.414 (4) | C93—C76 | 1.429 (5) |
C23—C24 | 1.361 (4) | C80—C79 | 1.395 (6) |
C19—C20 | 1.365 (4) | C80—C82 | 1.421 (6) |
C19—C18 | 1.408 (4) | C89—C88 | 1.393 (5) |
C19—H19 | 0.9500 | C89—C92 | 1.410 (5) |
C24—C25 | 1.464 (4) | C89—C90 | 1.441 (5) |
C25—C30 | 1.390 (4) | C76—C77 | 1.399 (5) |
C25—C26 | 1.395 (4) | C76—C91 | 1.430 (5) |
N4—C53 | 1.331 (4) | C92—C84 | 1.424 (5) |
N4—C52 | 1.342 (4) | C91—C90 | 1.344 (5) |
C27—C26 | 1.380 (4) | C91—H91 | 0.9500 |
C27—C28 | 1.394 (4) | C83—C82 | 1.336 (6) |
C16—C17 | 1.386 (4) | C83—C84 | 1.412 (5) |
C17—C18 | 1.380 (4) | C83—H83 | 0.9500 |
C17—H17 | 0.9500 | C90—H90 | 0.9500 |
C26—H26 | 0.9500 | C87—C86 | 1.368 (6) |
C30—C29 | 1.384 (4) | C87—C88 | 1.391 (6) |
C30—H30 | 0.9500 | C87—H87 | 0.9500 |
C52—C51 | 1.382 (5) | C88—H88 | 0.9500 |
C52—H52 | 0.9500 | C78—C79 | 1.376 (6) |
C51—C50 | 1.384 (4) | C78—C77 | 1.394 (6) |
C51—H51 | 0.9500 | C78—H78 | 0.9500 |
C29—C28 | 1.371 (4) | C82—H82 | 0.9500 |
C29—H29 | 0.9500 | C84—C86 | 1.401 (6) |
N3—C43 | 1.334 (4) | C86—H86 | 0.9500 |
N3—C47 | 1.334 (4) | C77—H77 | 0.9500 |
C49—C48 | 1.326 (5) | C79—H79 | 0.9500 |
C49—C50 | 1.465 (5) | C69—C75 | 1.388 (5) |
C49—H49 | 1.01 (3) | C69—C70 | 1.417 (5) |
C45—C46 | 1.384 (5) | C70—C70i | 1.411 (7) |
C45—C44 | 1.388 (5) | C70—C71 | 1.412 (5) |
C45—C48 | 1.477 (5) | C71—C73 | 1.398 (5) |
C50—C54 | 1.389 (5) | C73—C74 | 1.394 (5) |
C48—H48 | 1.09 (4) | C73—H73 | 0.9500 |
C43—C44 | 1.381 (5) | C75—C74 | 1.371 (5) |
C43—H43 | 0.9500 | C75—H75 | 0.9500 |
C44—H44 | 0.9500 | C74—H74 | 0.9500 |
C68i—C72—C71 | 122.1 (4) | C45—C46—H46 | 120.2 |
C68i—C72—H72 | 119.0 | N3—C47—C46 | 124.1 (4) |
C71—C72—H72 | 119.0 | N3—C47—H47 | 118.0 |
C72i—C68—C69 | 120.7 (4) | C46—C47—H47 | 118.0 |
C72i—C68—H68 | 119.6 | C31—N1—C35 | 116.8 (3) |
C69—C68—H68 | 119.6 | C41—N2—C40 | 116.8 (3) |
C1—O7—C9 | 121.9 (2) | C37—C36—C33 | 125.4 (4) |
C8—O4—H4O | 119 (3) | C37—C36—H36 | 120 (3) |
C3—O1—H1O | 110 (3) | C33—C36—H36 | 114 (3) |
C13—O6—H6O | 112 (2) | C39—C38—C42 | 117.7 (3) |
C12—O5—H5O | 116 (3) | C39—C38—C37 | 123.7 (3) |
C5—O2—H2O | 102 (3) | C42—C38—C37 | 118.6 (3) |
C8—C9—O7 | 120.0 (3) | C31—C32—C33 | 119.3 (3) |
C8—C9—C10 | 128.9 (3) | C31—C32—H32 | 120.4 |
O7—C9—C10 | 111.1 (3) | C33—C32—H32 | 120.4 |
C1—C2—C3 | 117.7 (3) | N1—C35—C34 | 123.2 (3) |
C1—C2—H2 | 121.1 | N1—C35—H35 | 118.4 |
C3—C2—H2 | 121.1 | C34—C35—H35 | 118.4 |
C11—C10—C15 | 118.1 (3) | C36—C37—C38 | 125.7 (3) |
C11—C10—C9 | 121.8 (3) | C36—C37—H37 | 121 (2) |
C15—C10—C9 | 120.0 (3) | C38—C37—H37 | 113 (2) |
O3—C7—C6 | 123.1 (3) | C32—C33—C34 | 117.1 (3) |
O3—C7—C8 | 119.8 (3) | C32—C33—C36 | 123.6 (3) |
C6—C7—C8 | 117.1 (3) | C34—C33—C36 | 119.3 (3) |
C1—C6—C5 | 117.9 (3) | C38—C39—C40 | 118.9 (3) |
C1—C6—C7 | 119.9 (3) | C38—C39—H39 | 120.5 |
C5—C6—C7 | 122.2 (3) | C40—C39—H39 | 120.5 |
O6—C13—C14 | 119.8 (3) | N2—C41—C42 | 123.4 (3) |
O6—C13—C12 | 120.8 (3) | N2—C41—H41 | 118.3 |
C14—C13—C12 | 119.4 (3) | C42—C41—H41 | 118.3 |
O7—C1—C2 | 117.0 (3) | C41—C42—C38 | 119.5 (3) |
O7—C1—C6 | 120.3 (3) | C41—C42—H42 | 120.3 |
C2—C1—C6 | 122.7 (3) | C38—C42—H42 | 120.3 |
O4—C8—C9 | 121.4 (3) | N1—C31—C32 | 123.9 (3) |
O4—C8—C7 | 117.8 (3) | N1—C31—H31 | 118.1 |
C9—C8—C7 | 120.8 (3) | C32—C31—H31 | 118.1 |
C5—C4—C3 | 119.2 (3) | C35—C34—C33 | 119.8 (3) |
C5—C4—H4 | 120.4 | C35—C34—H34 | 120.1 |
C3—C4—H4 | 120.4 | C33—C34—H34 | 120.1 |
C12—C11—C10 | 121.4 (3) | N2—C40—C39 | 123.8 (3) |
C12—C11—H11 | 119.3 | N2—C40—H40 | 118.1 |
C10—C11—H11 | 119.3 | C39—C40—H40 | 118.1 |
O5—C12—C11 | 123.5 (3) | C55—N5—C59 | 116.3 (4) |
O5—C12—C13 | 116.9 (3) | C65—N6—C64 | 115.6 (4) |
C11—C12—C13 | 119.6 (3) | N6—C65—C66 | 124.2 (4) |
C13—C14—C15 | 121.2 (3) | N6—C65—H65 | 117.9 |
C13—C14—H14 | 119.4 | C66—C65—H65 | 117.9 |
C15—C14—H14 | 119.4 | C57—C58—C59 | 120.1 (4) |
O1—C3—C2 | 121.9 (3) | C57—C58—H58 | 119.9 |
O1—C3—C4 | 116.4 (3) | C59—C58—H58 | 119.9 |
C2—C3—C4 | 121.7 (3) | C63—C62—C66 | 116.3 (4) |
C14—C15—C10 | 120.2 (3) | C63—C62—C61 | 120.0 (6) |
C14—C15—H15 | 119.9 | C66—C62—C61 | 123.8 (6) |
C10—C15—H15 | 119.9 | N5—C55—C56 | 124.6 (4) |
O2—C5—C4 | 120.6 (3) | N5—C55—H55 | 117.7 |
O2—C5—C6 | 118.7 (3) | C56—C55—H55 | 117.7 |
C4—C5—C6 | 120.7 (3) | N6—C64—C63 | 124.8 (5) |
C18—O8—H8O | 110 (2) | N6—C64—H64 | 117.6 |
C23—O11—H11O | 104 (4) | C63—C64—H64 | 117.6 |
C16—O14—C24 | 120.9 (2) | N5—C59—C58 | 122.2 (4) |
C27—O12—H12O | 107 (2) | N5—C59—H59 | 118.9 |
C28—O13—H13O | 111 (3) | C58—C59—H59 | 118.9 |
C20—O9—H9O | 103 (2) | C65—C66—C62 | 118.5 (4) |
O10—C22—C21 | 122.7 (3) | C65—C66—H66 | 120.8 |
O10—C22—C23 | 119.9 (3) | C62—C66—H66 | 120.8 |
C21—C22—C23 | 117.4 (3) | C61—C60—C57 | 138.1 (11) |
C16—C21—C20 | 117.6 (3) | C57—C56—C55 | 121.0 (5) |
C16—C21—C22 | 119.7 (3) | C57—C56—H56 | 119.5 |
C20—C21—C22 | 122.7 (3) | C55—C56—H56 | 119.5 |
C24—C23—O11 | 120.9 (3) | C60—C61—C62 | 139.7 (11) |
C24—C23—C22 | 120.7 (3) | C56—C57—C58 | 115.7 (4) |
O11—C23—C22 | 118.4 (3) | C56—C57—C60 | 120.2 (6) |
C20—C19—C18 | 119.2 (3) | C58—C57—C60 | 124.1 (6) |
C20—C19—H19 | 120.4 | C64—C63—C62 | 120.5 (5) |
C18—C19—H19 | 120.4 | C64—C63—H63 | 119.7 |
C23—C24—O14 | 120.5 (3) | C62—C63—H63 | 119.7 |
C23—C24—C25 | 128.8 (3) | C92—C93—C80 | 120.4 (4) |
O14—C24—C25 | 110.6 (3) | C92—C93—C76 | 119.4 (4) |
C30—C25—C26 | 118.2 (3) | C80—C93—C76 | 120.1 (4) |
C30—C25—C24 | 120.8 (3) | C79—C80—C82 | 123.4 (4) |
C26—C25—C24 | 120.9 (3) | C79—C80—C93 | 118.7 (4) |
C53—N4—C52 | 117.2 (3) | C82—C80—C93 | 117.8 (4) |
O12—C27—C26 | 124.0 (3) | C88—C89—C92 | 119.6 (4) |
O12—C27—C28 | 116.7 (3) | C88—C89—C90 | 122.2 (4) |
C26—C27—C28 | 119.2 (3) | C92—C89—C90 | 118.2 (4) |
O14—C16—C17 | 116.5 (3) | C77—C76—C93 | 118.7 (4) |
O14—C16—C21 | 120.8 (3) | C77—C76—C91 | 123.1 (4) |
C17—C16—C21 | 122.7 (3) | C93—C76—C91 | 118.2 (4) |
C18—C17—C16 | 117.8 (3) | C89—C92—C93 | 121.0 (4) |
C18—C17—H17 | 121.1 | C89—C92—C84 | 119.5 (4) |
C16—C17—H17 | 121.1 | C93—C92—C84 | 119.5 (4) |
C27—C26—C25 | 121.2 (3) | C90—C91—C76 | 122.1 (4) |
C27—C26—H26 | 119.4 | C90—C91—H91 | 118.9 |
C25—C26—H26 | 119.4 | C76—C91—H91 | 118.9 |
C29—C30—C25 | 120.9 (3) | C82—C83—C84 | 123.0 (4) |
C29—C30—H30 | 119.6 | C82—C83—H83 | 118.5 |
C25—C30—H30 | 119.6 | C84—C83—H83 | 118.5 |
O8—C18—C17 | 122.1 (3) | C91—C90—C89 | 121.1 (4) |
O8—C18—C19 | 116.3 (3) | C91—C90—H90 | 119.4 |
C17—C18—C19 | 121.6 (3) | C89—C90—H90 | 119.4 |
N4—C52—C51 | 122.7 (3) | C86—C87—C88 | 120.1 (4) |
N4—C52—H52 | 118.7 | C86—C87—H87 | 120.0 |
C51—C52—H52 | 118.7 | C88—C87—H87 | 120.0 |
O9—C20—C19 | 119.7 (3) | C87—C88—C89 | 120.7 (4) |
O9—C20—C21 | 119.2 (3) | C87—C88—H88 | 119.6 |
C19—C20—C21 | 121.1 (3) | C89—C88—H88 | 119.6 |
C52—C51—C50 | 120.4 (3) | C79—C78—C77 | 121.3 (5) |
C52—C51—H51 | 119.8 | C79—C78—H78 | 119.3 |
C50—C51—H51 | 119.8 | C77—C78—H78 | 119.3 |
C28—C29—C30 | 120.1 (3) | C83—C82—C80 | 121.3 (4) |
C28—C29—H29 | 120.0 | C83—C82—H82 | 119.3 |
C30—C29—H29 | 120.0 | C80—C82—H82 | 119.3 |
C43—N3—C47 | 115.9 (3) | C86—C84—C83 | 123.4 (4) |
C29—C28—O13 | 119.3 (3) | C86—C84—C92 | 118.7 (4) |
C29—C28—C27 | 120.4 (3) | C83—C84—C92 | 117.9 (4) |
O13—C28—C27 | 120.3 (3) | C87—C86—C84 | 121.5 (4) |
C48—C49—C50 | 125.8 (3) | C87—C86—H86 | 119.3 |
C48—C49—H49 | 119.4 (18) | C84—C86—H86 | 119.3 |
C50—C49—H49 | 114.6 (18) | C78—C77—C76 | 120.3 (4) |
C46—C45—C44 | 116.6 (3) | C78—C77—H77 | 119.9 |
C46—C45—C48 | 123.5 (3) | C76—C77—H77 | 119.9 |
C44—C45—C48 | 119.9 (3) | C78—C79—C80 | 120.9 (5) |
C51—C50—C54 | 116.1 (3) | C78—C79—H79 | 119.6 |
C51—C50—C49 | 123.8 (3) | C80—C79—H79 | 119.6 |
C54—C50—C49 | 120.0 (3) | C75—C69—C70 | 119.4 (3) |
C49—C48—C45 | 125.6 (3) | C75—C69—C68 | 122.2 (4) |
C49—C48—H48 | 120 (2) | C70—C69—C68 | 118.4 (3) |
C45—C48—H48 | 114 (2) | C70i—C70—C71 | 120.1 (4) |
N3—C43—C44 | 123.9 (3) | C70i—C70—C69 | 120.4 (4) |
N3—C43—H43 | 118.0 | C71—C70—C69 | 119.5 (3) |
C44—C43—H43 | 118.0 | C73—C71—C70 | 119.0 (3) |
C43—C44—C45 | 119.8 (3) | C73—C71—C72 | 122.8 (4) |
C43—C44—H44 | 120.1 | C70—C71—C72 | 118.2 (3) |
C45—C44—H44 | 120.1 | C74—C73—C71 | 120.9 (4) |
C53—C54—C50 | 120.4 (3) | C74—C73—H73 | 119.5 |
C53—C54—H54 | 119.8 | C71—C73—H73 | 119.5 |
C50—C54—H54 | 119.8 | C74—C75—C69 | 121.4 (4) |
N4—C53—C54 | 123.2 (3) | C74—C75—H75 | 119.3 |
N4—C53—H53 | 118.4 | C69—C75—H75 | 119.3 |
C54—C53—H53 | 118.4 | C75—C74—C73 | 119.8 (4) |
C47—C46—C45 | 119.6 (4) | C75—C74—H74 | 120.1 |
C47—C46—H46 | 120.2 | C73—C74—H74 | 120.1 |
Symmetry code: (i) −x+1, −y+1, −z. |
C34H24N2O7 | V = 1331.01 (13) Å3 |
Mr = 572.55 | Z = 2 |
Triclinic, P1 | F(000) = 596 |
a = 10.5919 (6) Å | Dx = 1.429 Mg m−3 |
b = 11.6067 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 11.6919 (7) Å | µ = 0.10 mm−1 |
α = 85.133 (4)° | T = 150 K |
β = 72.938 (3)° | Plate, yellow |
γ = 75.632 (3)° | 0.30 × 0.20 × 0.10 mm |
Absorption correction: analytical Bruker, AXS, 2008 | Rint = 0.050 |
Tmin = 0.976, Tmax = 0.990 | θmax = 26.4°, θmin = 1.8° |
20837 measured reflections | h = −13→13 |
5395 independent reflections | k = −14→14 |
3891 reflections with I > 2σ(I) | l = −14→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0633P)2 + 0.583P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
5395 reflections | Δρmax = 0.57 e Å−3 |
426 parameters | Δρmin = −0.33 e Å−3 |
C34H24N2O7 | γ = 75.632 (3)° |
Mr = 572.55 | V = 1331.01 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.5919 (6) Å | Mo Kα radiation |
b = 11.6067 (6) Å | µ = 0.10 mm−1 |
c = 11.6919 (7) Å | T = 150 K |
α = 85.133 (4)° | 0.30 × 0.20 × 0.10 mm |
β = 72.938 (3)° |
Absorption correction: analytical Bruker, AXS, 2008 | 5395 independent reflections |
Tmin = 0.976, Tmax = 0.990 | 3891 reflections with I > 2σ(I) |
20837 measured reflections | Rint = 0.050 |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.57 e Å−3 |
5395 reflections | Δρmin = −0.33 e Å−3 |
426 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O7 | 0.28875 (14) | 0.17889 (11) | 0.73374 (11) | 0.0235 (3) | |
O1 | 0.43739 (15) | −0.16238 (12) | 0.94580 (13) | 0.0285 (3) | |
O4 | 0.10867 (16) | 0.48243 (12) | 0.81474 (14) | 0.0324 (4) | |
O3 | 0.11478 (15) | 0.38118 (12) | 1.03171 (13) | 0.0328 (4) | |
O5 | 0.27963 (16) | 0.41368 (13) | 0.23721 (12) | 0.0329 (4) | |
O2 | 0.20553 (17) | 0.19528 (14) | 1.15910 (13) | 0.0385 (4) | |
C6 | 0.23822 (19) | 0.19391 (16) | 0.94674 (17) | 0.0209 (4) | |
C8 | 0.1672 (2) | 0.36431 (16) | 0.82332 (18) | 0.0239 (4) | |
C1 | 0.29578 (19) | 0.12753 (16) | 0.84244 (17) | 0.0210 (4) | |
O6 | 0.43058 (19) | 0.20806 (14) | 0.30374 (14) | 0.0466 (5) | |
C9 | 0.22658 (19) | 0.29656 (16) | 0.72403 (17) | 0.0210 (4) | |
C2 | 0.3624 (2) | 0.00965 (17) | 0.84069 (17) | 0.0232 (4) | |
H2 | 0.4005 | −0.0325 | 0.7677 | 0.028* | |
C7 | 0.16969 (19) | 0.31616 (17) | 0.94067 (18) | 0.0234 (4) | |
C10 | 0.23791 (19) | 0.33118 (16) | 0.59827 (17) | 0.0219 (4) | |
C4 | 0.3185 (2) | 0.01672 (17) | 1.05585 (18) | 0.0248 (4) | |
H4 | 0.3267 | −0.0223 | 1.1290 | 0.030* | |
C12 | 0.1752 (2) | 0.46722 (17) | 0.44504 (19) | 0.0288 (5) | |
H12 | 0.1231 | 0.5407 | 0.4240 | 0.035* | |
C13 | 0.2621 (2) | 0.39152 (17) | 0.35589 (18) | 0.0244 (4) | |
C15 | 0.3273 (2) | 0.25509 (16) | 0.50722 (18) | 0.0250 (5) | |
H15 | 0.3804 | 0.1820 | 0.5278 | 0.030* | |
C3 | 0.37255 (19) | −0.04627 (16) | 0.94875 (18) | 0.0223 (4) | |
C5 | 0.2536 (2) | 0.13506 (17) | 1.05533 (18) | 0.0247 (4) | |
C14 | 0.3396 (2) | 0.28431 (17) | 0.38836 (18) | 0.0264 (5) | |
C11 | 0.1621 (2) | 0.43851 (18) | 0.56502 (19) | 0.0290 (5) | |
H11 | 0.1013 | 0.4921 | 0.6249 | 0.035* | |
N1 | 0.16472 (17) | 0.63560 (14) | 0.17732 (16) | 0.0288 (4) | |
C22 | 0.1746 (2) | 0.6421 (2) | 0.0612 (2) | 0.0359 (5) | |
H22 | 0.2141 | 0.5712 | 0.0163 | 0.043* | |
C26 | 0.1092 (2) | 0.7365 (2) | 0.2375 (2) | 0.0389 (6) | |
H26 | 0.1009 | 0.7351 | 0.3207 | 0.047* | |
C24 | 0.0732 (2) | 0.8489 (2) | 0.0631 (3) | 0.0522 (8) | |
C23 | 0.1317 (3) | 0.7441 (3) | 0.0022 (2) | 0.0493 (7) | |
H23 | 0.1425 | 0.7427 | −0.0812 | 0.059* | |
C25 | 0.0629 (3) | 0.8440 (2) | 0.1840 (3) | 0.0510 (7) | |
H25 | 0.0243 | 0.9140 | 0.2304 | 0.061* | |
C27B | 0.0066 (7) | 0.9840 (8) | 0.0543 (9) | 0.025 (3) | 0.367 (17) |
C27A | 0.0317 (4) | 0.9469 (5) | −0.0204 (5) | 0.027 (2) | 0.633 (17) |
N2 | 0.45661 (18) | 0.72417 (15) | 0.15275 (16) | 0.0306 (4) | |
C18 | 0.4928 (2) | 0.56860 (18) | 0.34458 (19) | 0.0271 (5) | |
C21 | 0.5151 (2) | 0.4858 (2) | 0.44329 (19) | 0.0297 (5) | |
C19 | 0.5355 (2) | 0.52941 (19) | 0.2275 (2) | 0.0327 (5) | |
H19 | 0.5780 | 0.4481 | 0.2104 | 0.039* | |
C17 | 0.4289 (2) | 0.68874 (19) | 0.3626 (2) | 0.0334 (5) | |
H17 | 0.3958 | 0.7202 | 0.4411 | 0.040* | |
C20 | 0.5159 (2) | 0.60910 (19) | 0.1356 (2) | 0.0320 (5) | |
H20 | 0.5465 | 0.5801 | 0.0562 | 0.038* | |
C16 | 0.4141 (2) | 0.7617 (2) | 0.2654 (2) | 0.0356 (5) | |
H16 | 0.3711 | 0.8434 | 0.2796 | 0.043* | |
C28 | 0.1124 (3) | 0.9670 (2) | 0.5470 (2) | 0.0433 (6) | |
C34 | 0.0853 (3) | 1.0764 (2) | 0.4901 (2) | 0.0476 (6) | |
H34 | 0.1432 | 1.1288 | 0.4837 | 0.057* | |
C31 | 0.1597 (3) | 0.7452 (2) | 0.6639 (2) | 0.0492 (7) | |
H31 | 0.1773 | 0.6701 | 0.7028 | 0.059* | |
C33 | 0.0249 (3) | 0.8884 (2) | 0.5578 (2) | 0.0398 (6) | |
C29 | 0.2244 (3) | 0.9313 (2) | 0.5993 (2) | 0.0489 (7) | |
C32 | 0.0541 (3) | 0.7762 (2) | 0.6155 (2) | 0.0467 (6) | |
H32 | −0.0013 | 0.7219 | 0.6202 | 0.056* | |
C30 | 0.2437 (3) | 0.8249 (2) | 0.6566 (2) | 0.0479 (7) | |
H30 | 0.3157 | 0.8030 | 0.6929 | 0.057* | |
H27 | 0.039 (3) | 0.942 (2) | −0.105 (2) | 0.042 (7)* | |
H21 | 0.557 (3) | 0.407 (2) | 0.418 (2) | 0.047 (7)* | |
H2O | 0.163 (3) | 0.279 (3) | 1.142 (3) | 0.074 (9)* | |
H6O | 0.424 (3) | 0.233 (3) | 0.231 (3) | 0.077 (10)* | |
H1O | 0.439 (3) | −0.193 (3) | 1.025 (3) | 0.082 (10)* | |
H5O | 0.239 (3) | 0.494 (3) | 0.223 (3) | 0.076 (10)* | |
H4O | 0.037 (4) | 0.509 (3) | 0.901 (3) | 0.104 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O7 | 0.0316 (8) | 0.0165 (7) | 0.0186 (7) | 0.0017 (6) | −0.0082 (6) | 0.0035 (5) |
O1 | 0.0397 (9) | 0.0192 (7) | 0.0215 (8) | 0.0033 (6) | −0.0105 (7) | 0.0046 (6) |
O4 | 0.0439 (9) | 0.0161 (7) | 0.0269 (8) | 0.0049 (6) | −0.0053 (7) | 0.0033 (6) |
O3 | 0.0431 (9) | 0.0235 (8) | 0.0247 (8) | 0.0048 (6) | −0.0087 (7) | −0.0028 (6) |
O5 | 0.0513 (10) | 0.0222 (8) | 0.0220 (8) | 0.0012 (7) | −0.0157 (7) | 0.0060 (6) |
O2 | 0.0586 (11) | 0.0281 (8) | 0.0196 (8) | 0.0073 (7) | −0.0108 (7) | −0.0033 (6) |
C6 | 0.0218 (10) | 0.0198 (9) | 0.0198 (10) | −0.0039 (8) | −0.0051 (8) | 0.0012 (8) |
C8 | 0.0260 (11) | 0.0161 (9) | 0.0262 (11) | −0.0012 (8) | −0.0067 (9) | 0.0041 (8) |
C1 | 0.0240 (10) | 0.0203 (10) | 0.0178 (10) | −0.0038 (8) | −0.0073 (8) | 0.0059 (8) |
O6 | 0.0706 (12) | 0.0322 (9) | 0.0203 (9) | 0.0218 (8) | −0.0156 (8) | −0.0020 (7) |
C9 | 0.0218 (10) | 0.0148 (9) | 0.0239 (11) | −0.0011 (7) | −0.0065 (8) | 0.0043 (8) |
C2 | 0.0281 (11) | 0.0212 (10) | 0.0178 (10) | −0.0015 (8) | −0.0063 (8) | −0.0004 (8) |
C7 | 0.0233 (10) | 0.0221 (10) | 0.0216 (11) | −0.0032 (8) | −0.0034 (8) | −0.0004 (8) |
C10 | 0.0237 (10) | 0.0194 (10) | 0.0213 (10) | −0.0044 (8) | −0.0063 (8) | 0.0043 (8) |
C4 | 0.0295 (11) | 0.0240 (10) | 0.0193 (10) | −0.0030 (8) | −0.0086 (9) | 0.0051 (8) |
C12 | 0.0304 (11) | 0.0202 (10) | 0.0306 (12) | 0.0040 (8) | −0.0112 (10) | 0.0071 (9) |
C13 | 0.0327 (11) | 0.0199 (10) | 0.0216 (11) | −0.0045 (8) | −0.0125 (9) | 0.0065 (8) |
C15 | 0.0325 (11) | 0.0161 (9) | 0.0254 (11) | 0.0003 (8) | −0.0134 (9) | 0.0054 (8) |
C3 | 0.0247 (10) | 0.0154 (9) | 0.0255 (11) | −0.0012 (8) | −0.0093 (9) | 0.0036 (8) |
C5 | 0.0285 (11) | 0.0245 (10) | 0.0188 (10) | −0.0027 (8) | −0.0060 (9) | −0.0009 (8) |
C14 | 0.0344 (12) | 0.0187 (10) | 0.0236 (11) | 0.0019 (8) | −0.0113 (9) | 0.0001 (8) |
C11 | 0.0307 (11) | 0.0226 (10) | 0.0262 (11) | 0.0030 (9) | −0.0055 (9) | 0.0032 (9) |
N1 | 0.0318 (10) | 0.0212 (9) | 0.0333 (10) | −0.0040 (7) | −0.0136 (8) | 0.0091 (7) |
C22 | 0.0405 (13) | 0.0348 (12) | 0.0329 (13) | −0.0084 (10) | −0.0131 (11) | 0.0062 (10) |
C26 | 0.0457 (14) | 0.0318 (12) | 0.0377 (14) | −0.0085 (11) | −0.0103 (11) | 0.0013 (10) |
C24 | 0.0308 (13) | 0.0416 (15) | 0.087 (2) | −0.0156 (11) | −0.0271 (14) | 0.0436 (15) |
C23 | 0.0502 (16) | 0.0607 (18) | 0.0450 (16) | −0.0220 (14) | −0.0264 (13) | 0.0303 (13) |
C25 | 0.0376 (14) | 0.0175 (11) | 0.088 (2) | −0.0009 (10) | −0.0066 (14) | −0.0014 (12) |
C27B | 0.031 (3) | 0.021 (5) | 0.020 (7) | −0.001 (3) | −0.008 (3) | 0.004 (4) |
C27A | 0.033 (2) | 0.025 (3) | 0.022 (4) | −0.0054 (19) | −0.010 (2) | 0.007 (2) |
N2 | 0.0343 (10) | 0.0312 (10) | 0.0268 (10) | −0.0076 (8) | −0.0131 (8) | 0.0128 (8) |
C18 | 0.0265 (11) | 0.0291 (11) | 0.0276 (12) | −0.0088 (9) | −0.0120 (9) | 0.0117 (9) |
C21 | 0.0318 (12) | 0.0267 (11) | 0.0304 (11) | −0.0064 (9) | −0.0119 (10) | 0.0107 (9) |
C19 | 0.0378 (13) | 0.0262 (11) | 0.0328 (13) | −0.0035 (9) | −0.0134 (10) | 0.0075 (9) |
C17 | 0.0427 (13) | 0.0314 (12) | 0.0239 (12) | −0.0042 (10) | −0.0120 (10) | 0.0080 (9) |
C20 | 0.0380 (13) | 0.0347 (12) | 0.0235 (11) | −0.0089 (10) | −0.0110 (10) | 0.0081 (9) |
C16 | 0.0459 (14) | 0.0280 (11) | 0.0309 (13) | −0.0033 (10) | −0.0145 (11) | 0.0077 (9) |
C28 | 0.0572 (16) | 0.0341 (13) | 0.0374 (14) | −0.0097 (12) | −0.0102 (12) | −0.0080 (11) |
C34 | 0.0589 (17) | 0.0431 (15) | 0.0467 (16) | −0.0227 (13) | −0.0153 (13) | 0.0012 (12) |
C31 | 0.0621 (18) | 0.0411 (14) | 0.0386 (15) | −0.0083 (13) | −0.0085 (13) | −0.0011 (11) |
C33 | 0.0511 (15) | 0.0353 (13) | 0.0321 (13) | −0.0134 (11) | −0.0066 (11) | −0.0039 (10) |
C29 | 0.0606 (17) | 0.0427 (15) | 0.0465 (16) | −0.0095 (13) | −0.0204 (14) | −0.0074 (12) |
C32 | 0.0564 (17) | 0.0387 (14) | 0.0430 (15) | −0.0158 (12) | −0.0074 (13) | 0.0008 (11) |
C30 | 0.0561 (17) | 0.0421 (15) | 0.0443 (16) | −0.0060 (12) | −0.0143 (13) | −0.0098 (12) |
O7—C1 | 1.372 (2) | C26—H26 | 0.9500 |
O7—C9 | 1.372 (2) | C24—C23 | 1.372 (4) |
O1—C3 | 1.350 (2) | C24—C25 | 1.383 (4) |
O1—H1O | 0.96 (3) | C24—C27A | 1.502 (5) |
O4—C8 | 1.366 (2) | C24—C27B | 1.560 (9) |
O4—H4O | 1.08 (4) | C23—H23 | 0.9500 |
O3—C7 | 1.263 (2) | C25—H25 | 0.9500 |
O5—C13 | 1.356 (2) | C27B—C27Ai | 0.919 (6) |
O5—H5O | 0.95 (3) | C27B—C27A | 0.944 (7) |
O2—C5 | 1.351 (2) | C27B—C27Bi | 1.33 (2) |
O2—H2O | 0.99 (3) | C27A—C27Bi | 0.919 (6) |
C6—C1 | 1.394 (3) | C27A—C27Ai | 1.304 (12) |
C6—C5 | 1.423 (3) | C27A—H27 | 0.98 (3) |
C6—C7 | 1.431 (3) | N2—C20 | 1.332 (3) |
C8—C9 | 1.357 (3) | N2—C16 | 1.334 (3) |
C8—C7 | 1.442 (3) | C18—C19 | 1.387 (3) |
C1—C2 | 1.374 (3) | C18—C17 | 1.395 (3) |
O6—C14 | 1.362 (3) | C18—C21 | 1.473 (3) |
O6—H6O | 0.89 (3) | C21—C21ii | 1.320 (4) |
C9—C10 | 1.469 (3) | C21—H21 | 0.94 (3) |
C2—C3 | 1.391 (3) | C19—C20 | 1.385 (3) |
C2—H2 | 0.9500 | C19—H19 | 0.9500 |
C10—C11 | 1.397 (3) | C17—C16 | 1.382 (3) |
C10—C15 | 1.401 (3) | C17—H17 | 0.9500 |
C4—C5 | 1.376 (3) | C20—H20 | 0.9500 |
C4—C3 | 1.399 (3) | C16—H16 | 0.9500 |
C4—H4 | 0.9500 | C28—C34 | 1.387 (4) |
C12—C13 | 1.377 (3) | C28—C33 | 1.427 (3) |
C12—C11 | 1.388 (3) | C28—C29 | 1.447 (4) |
C12—H12 | 0.9500 | C34—C33iii | 1.398 (4) |
C13—C14 | 1.401 (3) | C34—H34 | 0.9500 |
C15—C14 | 1.378 (3) | C31—C32 | 1.356 (4) |
C15—H15 | 0.9500 | C31—C30 | 1.416 (4) |
C11—H11 | 0.9500 | C31—H31 | 0.9500 |
N1—C22 | 1.328 (3) | C33—C34iii | 1.397 (4) |
N1—C26 | 1.330 (3) | C33—C32 | 1.422 (3) |
C22—C23 | 1.364 (3) | C29—C30 | 1.353 (4) |
C22—H22 | 0.9500 | C32—H32 | 0.9500 |
C26—C25 | 1.390 (3) | C30—H30 | 0.9500 |
C1—O7—C9 | 121.37 (15) | C25—C24—C27B | 97.7 (5) |
C3—O1—H1O | 111.4 (19) | C27A—C24—C27B | 35.8 (3) |
C8—O4—H4O | 107.2 (19) | C22—C23—C24 | 120.2 (2) |
C13—O5—H5O | 110.9 (19) | C22—C23—H23 | 119.9 |
C5—O2—H2O | 108.5 (18) | C24—C23—H23 | 119.9 |
C1—C6—C5 | 117.02 (17) | C24—C25—C26 | 119.9 (2) |
C1—C6—C7 | 119.80 (17) | C24—C25—H25 | 120.0 |
C5—C6—C7 | 123.18 (18) | C26—C25—H25 | 120.0 |
C9—C8—O4 | 120.90 (17) | C27Ai—C27B—C27A | 88.9 (13) |
C9—C8—C7 | 121.46 (17) | C27Ai—C27B—C27Bi | 45.2 (7) |
O4—C8—C7 | 117.56 (17) | C27A—C27B—C27Bi | 43.7 (7) |
O7—C1—C2 | 116.10 (17) | C27Ai—C27B—C24 | 157.2 (14) |
O7—C1—C6 | 120.50 (16) | C27A—C27B—C24 | 68.7 (7) |
C2—C1—C6 | 123.40 (17) | C27Bi—C27B—C24 | 112.3 (11) |
C14—O6—H6O | 110 (2) | C27Bi—C27A—C27B | 91.1 (13) |
C8—C9—O7 | 120.25 (16) | C27Bi—C27A—C27Ai | 46.3 (8) |
C8—C9—C10 | 128.90 (17) | C27B—C27A—C27Ai | 44.8 (7) |
O7—C9—C10 | 110.85 (16) | C27Bi—C27A—C24 | 165.9 (12) |
C1—C2—C3 | 118.21 (18) | C27B—C27A—C24 | 75.5 (7) |
C1—C2—H2 | 120.9 | C27Ai—C27A—C24 | 120.1 (7) |
C3—C2—H2 | 120.9 | C27Bi—C27A—H27 | 65 (2) |
O3—C7—C6 | 123.05 (18) | C27B—C27A—H27 | 155.8 (19) |
O3—C7—C8 | 120.35 (17) | C27Ai—C27A—H27 | 111.0 (18) |
C6—C7—C8 | 116.59 (17) | C24—C27A—H27 | 128.7 (16) |
C11—C10—C15 | 117.98 (18) | C20—N2—C16 | 116.72 (18) |
C11—C10—C9 | 122.30 (18) | C19—C18—C17 | 116.61 (18) |
C15—C10—C9 | 119.71 (16) | C19—C18—C21 | 120.75 (19) |
C5—C4—C3 | 120.07 (17) | C17—C18—C21 | 122.6 (2) |
C5—C4—H4 | 120.0 | C21ii—C21—C18 | 126.0 (3) |
C3—C4—H4 | 120.0 | C21ii—C21—H21 | 121.2 (16) |
C13—C12—C11 | 121.42 (18) | C18—C21—H21 | 112.9 (16) |
C13—C12—H12 | 119.3 | C20—C19—C18 | 119.9 (2) |
C11—C12—H12 | 119.3 | C20—C19—H19 | 120.1 |
O5—C13—C12 | 124.54 (17) | C18—C19—H19 | 120.1 |
O5—C13—C14 | 116.86 (18) | C16—C17—C18 | 119.4 (2) |
C12—C13—C14 | 118.60 (18) | C16—C17—H17 | 120.3 |
C14—C15—C10 | 121.24 (17) | C18—C17—H17 | 120.3 |
C14—C15—H15 | 119.4 | N2—C20—C19 | 123.5 (2) |
C10—C15—H15 | 119.4 | N2—C20—H20 | 118.3 |
O1—C3—C2 | 117.57 (17) | C19—C20—H20 | 118.3 |
O1—C3—C4 | 121.70 (17) | N2—C16—C17 | 123.9 (2) |
C2—C3—C4 | 120.73 (17) | N2—C16—H16 | 118.1 |
O2—C5—C4 | 119.22 (18) | C17—C16—H16 | 118.1 |
O2—C5—C6 | 120.24 (17) | C34—C28—C33 | 119.3 (2) |
C4—C5—C6 | 120.53 (18) | C34—C28—C29 | 122.0 (2) |
O6—C14—C15 | 118.58 (17) | C33—C28—C29 | 118.7 (2) |
O6—C14—C13 | 121.03 (18) | C28—C34—C33iii | 121.8 (2) |
C15—C14—C13 | 120.37 (18) | C28—C34—H34 | 119.1 |
C12—C11—C10 | 120.38 (19) | C33iii—C34—H34 | 119.1 |
C12—C11—H11 | 119.8 | C32—C31—C30 | 119.9 (3) |
C10—C11—H11 | 119.8 | C32—C31—H31 | 120.1 |
C22—N1—C26 | 116.33 (19) | C30—C31—H31 | 120.1 |
N1—C22—C23 | 124.2 (2) | C34iii—C33—C32 | 122.2 (2) |
N1—C22—H22 | 117.9 | C34iii—C33—C28 | 118.9 (2) |
C23—C22—H22 | 117.9 | C32—C33—C28 | 118.9 (2) |
N1—C26—C25 | 122.9 (2) | C30—C29—C28 | 119.4 (2) |
N1—C26—H26 | 118.5 | C31—C32—C33 | 121.1 (2) |
C25—C26—H26 | 118.5 | C31—C32—H32 | 119.4 |
C23—C24—C25 | 116.4 (2) | C33—C32—H32 | 119.4 |
C23—C24—C27A | 110.1 (3) | C29—C30—C31 | 122.0 (3) |
C25—C24—C27A | 133.6 (4) | C29—C30—H30 | 119.0 |
C23—C24—C27B | 145.9 (5) | C31—C30—H30 | 119.0 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O6iv | 0.95 | 2.38 | 3.138 (2) | 137 |
C22—H22···O3v | 0.95 | 2.64 | 3.309 (3) | 128 |
O2—H2O···O3 | 0.99 (3) | 1.78 (3) | 2.658 (2) | 145 (3) |
O6—H6O···O1iv | 0.89 (3) | 2.24 (3) | 2.872 (2) | 128 (3) |
O6—H6O···O5 | 0.89 (3) | 2.26 (3) | 2.716 (2) | 112 (2) |
O1—H1O···N2vi | 0.96 (3) | 1.74 (3) | 2.692 (2) | 169 (3) |
O5—H5O···N1 | 0.95 (3) | 1.75 (3) | 2.691 (2) | 172 (3) |
O4—H4O···O3vii | 1.08 (4) | 1.80 (4) | 2.731 (2) | 141 (3) |
Symmetry codes: (iv) −x+1, −y, −z+1; (v) x, y, z−1; (vi) x, y−1, z+1; (vii) −x, −y+1, −z+2. |
Experimental details
(QTMP_I) | (QTMP_II) | (QTMP_III) | (QTMP_IV) | |
Crystal data | ||||
Chemical formula | C39H46N6O7 | C31H34N4O7 | C27H30N2O9 | C27H30N2O8 |
Mr | 710.82 | 574.62 | 526.53 | 510.53 |
Crystal system, space group | Monoclinic, Pc | Monoclinic, P21/c | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 150 | 150 | 150 | 150 |
a, b, c (Å) | 9.0760 (13), 8.9616 (13), 22.501 (3) | 15.831 (2), 9.3122 (13), 20.211 (3) | 9.3506 (7), 10.9120 (8), 13.002 (1) | 9.3202 (10), 10.7538 (12), 12.9869 (14) |
α, β, γ (°) | 90, 93.554 (7), 90 | 90, 104.415 (7), 90 | 76.798 (5), 84.048 (6), 81.580 (6) | 79.471 (6), 85.133 (6), 82.377 (6) |
V (Å3) | 1826.6 (5) | 2885.7 (7) | 1274.26 (17) | 1266.0 (2) |
Z | 2 | 4 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.10 | 0.10 | 0.10 |
Crystal size (mm) | 0.45 × 0.25 × 0.20 | 0.45 × 0.40 × 0.12 | 0.40 × 0.40 × 0.15 | 0.60 × 0.40 × 0.15 |
Data collection | ||||
Diffractometer | ? | ? | ? | ? |
Absorption correction | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication |
Tmin, Tmax | 0.728, 1.000 | 0.821, 1.000 | 0.752, 1.000 | 0.844, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18413, 8351, 6243 | 22578, 6558, 4018 | 13650, 5832, 4470 | 13412, 5779, 4277 |
Rint | 0.062 | 0.077 | 0.034 | 0.030 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 | 0.649 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.130, 1.04 | 0.063, 0.163, 0.96 | 0.052, 0.159, 0.93 | 0.070, 0.202, 1.06 |
No. of reflections | 8351 | 6558 | 5832 | 5779 |
No. of parameters | 489 | 399 | 363 | 354 |
No. of restraints | 2 | 0 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0535P)2 + 0.2309P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0734P)2 + 1.8069P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0967P)2 + 0.5735P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.102P)2 + 1.1876P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.25, −0.27 | 0.32, −0.33 | 0.29, −0.39 | 0.80, −0.62 |
Absolute structure | Flack x determined using 2448 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). | ? | ? | ? |
Absolute structure parameter | 0.5 (8) | ? | ? | ? |
(QBP_I) | (QBP_II) | (QBP_III) | (QBP_IV) | |
Crystal data | ||||
Chemical formula | C29H26N2O9 | C29H18N2O8 | C30H22N3O7 | C45H36N6O8 |
Mr | 546.52 | 522.45 | 536.50 | 788.80 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 150 | 150 | 150 | 150 |
a, b, c (Å) | 9.8334 (7), 10.7098 (8), 13.0790 (9) | 9.806 (2), 10.778 (2), 13.055 (3) | 9.844 (5), 10.636 (6), 13.071 (7) | 10.0222 (12), 12.8756 (16), 15.0597 (18) |
α, β, γ (°) | 102.815 (7), 95.031 (7), 106.846 (7) | 102.833 (7), 94.525 (7), 106.943 (7) | 98.324 (7), 94.601 (7), 107.947 (8) | 81.685 (6), 83.118 (6), 76.273 (5) |
V (Å3) | 1268.29 (17) | 1271.6 (5) | 1277.0 (11) | 1860.6 (4) |
Z | 2 | 2 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.10 | 0.10 | 0.10 |
Crystal size (mm) | 1.00 × 0.50 × 0.20 | 0.60 × 0.30 × 0.25 | 0.65 × 0.45 × 0.30 | 0.65 × 0.50 × 0.25 |
Data collection | ||||
Diffractometer | ? | ? | ? | ? |
Absorption correction | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication |
Tmin, Tmax | 0.898, 1.000 | 0.741, 1.000 | 0.857, 1.000 | 0.804, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13454, 5791, 5160 | 10628, 4943, 3753 | 13246, 5767, 4834 | 19338, 8502, 6720 |
Rint | 0.016 | 0.037 | 0.022 | 0.031 |
(sin θ/λ)max (Å−1) | 0.649 | 0.617 | 0.648 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.110, 1.05 | 0.075, 0.214, 1.06 | 0.043, 0.114, 1.04 | 0.045, 0.134, 0.88 |
No. of reflections | 5791 | 4943 | 5767 | 8502 |
No. of parameters | 381 | 372 | 381 | 560 |
No. of restraints | 0 | 0 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0579P)2 + 0.5172P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.103P)2 + 1.8694P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0543P)2 + 0.4614P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0836P)2 + 0.7989P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.34, −0.23 | 1.14, −0.90 | 0.34, −0.21 | 0.31, −0.21 |
Absolute structure | ? | ? | ? | ? |
Absolute structure parameter | ? | ? | ? | ? |
(QDP_I) | (QDP_II) | (QDP_III) | (QDP_IV) | |
Crystal data | ||||
Chemical formula | C31H28N2O9 | C31H28N2O8 | C30H26N3O8 | C39H30N4O7 |
Mr | 572.55 | 556.55 | 556.54 | 666.67 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 150 | 293 | 150 | 150 |
a, b, c (Å) | 10.1899 (9), 11.6532 (11), 13.0214 (12) | 10.0381 (7), 11.5707 (8), 13.0194 (9) | 9.9867 (15), 11.2949 (17), 13.040 (2) | 18.0656 (11), 11.6584 (6), 16.661 (1) |
α, β, γ (°) | 97.351 (7), 95.446 (7), 115.237 (8) | 76.744 (5), 84.502 (6), 65.573 (5) | 79.558 (6), 85.192 (6), 66.082 (5) | 90, 115.565 (2), 90 |
V (Å3) | 1367.8 (2) | 1340.13 (17) | 1322.2 (4) | 3165.5 (3) |
Z | 2 | 2 | 2 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.10 | 0.10 | 0.10 |
Crystal size (mm) | 0.50 × 0.25 × 0.15 | 0.40 × 0.20 × 0.20 | 0.40 × 0.20 × 0.12 | 0.30 × 0.20 × 0.15 |
Data collection | ||||
Diffractometer | ? | ? | ? | ? |
Absorption correction | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication | Analytical Bruker, AXS, 2008 |
Tmin, Tmax | 0.818, 1.000 | 0.794, 1.000 | 0.747, 1.000 | 0.977, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14650, 6248, 4498 | 14382, 6106, 4337 | 13781, 6040, 3745 | 27138, 7197, 5739 |
Rint | 0.035 | 0.034 | 0.052 | 0.038 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 | 0.649 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.132, 1.02 | 0.057, 0.162, 1.03 | 0.063, 0.178, 1.02 | 0.047, 0.119, 1.04 |
No. of reflections | 6248 | 6106 | 6040 | 7197 |
No. of parameters | 407 | 398 | 400 | 497 |
No. of restraints | 0 | 0 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0598P)2 + 0.4848P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0802P)2 + 0.6053P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0779P)2 + 0.8181P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0488P)2 + 1.7932P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.28, −0.23 | 0.48, −0.48 | 0.49, −0.41 | 0.68, −0.44 |
Absolute structure | ? | ? | ? | ? |
Absolute structure parameter | ? | ? | ? | ? |
(QDP_V) | (QDPE_I) | (QDPE_II) | (QDPE_III) | |
Crystal data | ||||
Chemical formula | C27H20N2O7 | C31H30N2O8 | C39H34N4O7 | C27H22N2O7 |
Mr | 484.45 | 558.57 | 670.70 | 486.46 |
Crystal system, space group | Monoclinic, C2/c | Triclinic, P1 | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 150 | 150 | 150 | 296 |
a, b, c (Å) | 21.831 (5), 12.904 (3), 15.876 (4) | 9.8782 (8), 11.5881 (10), 13.041 (1) | 20.028 (3), 10.5025 (13), 16.5786 (18) | 13.3624 (4), 10.5540 (4), 32.5542 (10) |
α, β, γ (°) | 90, 101.912 (7), 90 | 76.595 (5), 85.792 (6), 67.035 (5) | 90, 108.851 (4), 90 | 90, 95.517 (3), 90 |
V (Å3) | 4376.0 (17) | 1336.8 (2) | 3300.2 (7) | 4569.7 (3) |
Z | 8 | 2 | 4 | 8 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.10 | 0.09 | 0.10 |
Crystal size (mm) | 0.30 × 0.20 × 0.12 | 0.40 × 0.20 × 0.20 | 0.25 × 0.12 × 0.12 | 0.35 × 0.25 × 0.15 |
Data collection | ||||
Diffractometer | ? | ? | ? | ? |
Absorption correction | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication | Analytical Bruker, AXS, 2008 | Multi-scan Empirical absorption correction |
Tmin, Tmax | 0.777, 1.000 | 0.777, 1.000 | 0.987, 0.989 | 0.808, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18633, 5006, 3202 | 14292, 6112, 4658 | 36152, 7537, 5491 | 43116, 10476, 7148 |
Rint | 0.071 | 0.036 | 0.053 | 0.050 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 | 0.650 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.150, 1.05 | 0.054, 0.148, 1.04 | 0.045, 0.113, 1.04 | 0.053, 0.150, 1.02 |
No. of reflections | 5006 | 6112 | 7537 | 10476 |
No. of parameters | 354 | 390 | 471 | 689 |
No. of restraints | 0 | 0 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0666P)2 + 1.7713P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0694P)2 + 0.7053P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.7852P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0612P)2 + 1.213P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.27, −0.32 | 0.44, −0.41 | 0.34, −0.29 | 0.22, −0.28 |
Absolute structure | ? | ? | ? | ? |
Absolute structure parameter | ? | ? | ? | ? |
(QAP_1) | (QAP_II) | (QPH_I) | (QPH_II) | |
Crystal data | ||||
Chemical formula | C29H26N4O8 | C25H18N4O7 | C31H26N2O9 | C33H22N3O7 |
Mr | 558.54 | 486.43 | 570.54 | 572.53 |
Crystal system, space group | Triclinic, P1 | Monoclinic, C2/c | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 150 | 150 | 150 | 150 |
a, b, c (Å) | 10.0918 (17), 11.4244 (19), 13.052 (2) | 21.647 (3), 12.8623 (16), 15.712 (2) | 8.1859 (13), 12.787 (2), 13.173 (2) | 8.416 (3), 12.297 (4), 13.111 (4) |
α, β, γ (°) | 98.573 (7), 95.190 (7), 115.078 (8) | 90, 101.543 (7), 90 | 83.634 (6), 83.848 (6), 73.246 (5) | 87.100 (6), 84.103 (6), 73.503 (5) |
V (Å3) | 1327.8 (4) | 4286.2 (10) | 1308.0 (4) | 1293.9 (7) |
Z | 2 | 8 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.11 | 0.11 | 0.11 |
Crystal size (mm) | 0.30 × 0.20 × 0.12 | 0.35 × 0.20 × 0.15 | 0.45 × 0.25 × 0.12 | 0.30 × 0.20 × 0.10 |
Data collection | ||||
Diffractometer | ? | ? | ? | ? |
Absorption correction | Multi-scan Jacobson, R. (1998) Private communication | Analytical Bruker, AXS, 2008 | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication |
Tmin, Tmax | 0.613, 1.000 | 0.973, 0.983 | 0.872, 1.000 | 0.462, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11363, 5197, 3551 | 24298, 4173, 3253 | 12319, 5126, 4074 | 10572, 5028, 2322 |
Rint | 0.074 | 0.051 | 0.032 | 0.128 |
(sin θ/λ)max (Å−1) | 0.617 | 0.617 | 0.617 | 0.617 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.090, 0.265, 1.17 | 0.052, 0.136, 0.89 | 0.054, 0.144, 1.08 | 0.085, 0.216, 0.99 |
No. of reflections | 5197 | 4173 | 5126 | 5028 |
No. of parameters | 390 | 345 | 396 | 402 |
No. of restraints | 0 | 0 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0982P)2 + 2.1601P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0625P)2 + 17.9666P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0626P)2 + 1.188P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0866P)2] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 1.80, −0.36 | 0.29, −0.30 | 1.38, −0.43 | 0.33, −0.30 |
Absolute structure | ? | ? | ? | ? |
Absolute structure parameter | ? | ? | ? | ? |
(QPH_III) | (QPH_IV) | (QPH_V) | (QBP_22TP) | |
Crystal data | ||||
Chemical formula | C58H42N7O8 | C33H22N3O8 | C33H22N3O7 | C29H21N2O7S |
Mr | 964.98 | 588.53 | 572.53 | 541.54 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 150 | 296 | 150 | 150 |
a, b, c (Å) | 9.9945 (3), 13.4346 (4), 17.8220 (5) | 9.4800 (7), 11.2614 (9), 13.5129 (10) | 4.983, 15.381, 18.142 | 9.8066 (9), 10.4874 (10), 13.0073 (12) |
α, β, γ (°) | 81.016 (1), 78.335 (1), 86.046 (1) | 104.785 (4), 108.855 (4), 90.687 (4) | 112.21, 94.99, 94.92 | 97.993 (7), 94.646 (7), 108.150 (8) |
V (Å3) | 2313.09 (12) | 1312.94 (18) | 1271.8 | 1247.8 (2) |
Z | 2 | 2 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.11 | 0.11 | 0.18 |
Crystal size (mm) | 0.25 × 0.22 × 0.10 | 0.25 × 0.20 × 0.20 | 0.50 × 0.20 × 0.10 | 0.55 × 0.20 × 0.15 |
Data collection | ||||
Diffractometer | ? | ? | ? | ? |
Absorption correction | Analytical Bruker, AXS, 2008 | Analytical Bruker, AXS, 2008 | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication |
Tmin, Tmax | 0.977, 0.991 | 0.974, 0.979 | 0.698, 1.000 | 0.835, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29578, 10501, 7634 | 14918, 5100, 3747 | 13154, 5827, 3470 | 13323, 5709, 4354 |
Rint | 0.033 | 0.042 | 0.066 | 0.031 |
(sin θ/λ)max (Å−1) | 0.650 | 0.617 | 0.649 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.120, 1.03 | 0.046, 0.123, 0.99 | 0.061, 0.155, 0.97 | 0.053, 0.142, 1.06 |
No. of reflections | 10501 | 5100 | 5827 | 5709 |
No. of parameters | 683 | 417 | 408 | 372 |
No. of restraints | 0 | 0 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0529P)2 + 0.6577P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0602P)2 + 0.3828P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0589P)2 + 0.7384P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.065P)2 + 0.7749P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.36, −0.37 | 0.45, −0.33 | 0.24, −0.30 | 0.42, −0.67 |
Absolute structure | ? | ? | ? | ? |
Absolute structure parameter | ? | ? | ? | ? |
(QBP_TTF) | (QDP_22TP) | (QDP_PYR) | (QDP_ANT) | |
Crystal data | ||||
Chemical formula | C69H50N6O14S6 | C30H20N2O7S | C90H63N6O14 | C34H24N2O7 |
Mr | 1379.51 | 552.54 | 1452.46 | 572.55 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 150 | 150 | 150 | 150 |
a, b, c (Å) | 12.547 (2), 13.299 (2), 18.490 (3) | 9.974, 11.421, 13.009 | 12.664, 13.235, 22.191 | 10.5919 (6), 11.6067 (6), 11.6919 (7) |
α, β, γ (°) | 94.246 (7), 90.204 (6), 98.776 (7) | 78.51, 85.22, 66.39 | 104.03, 96.59, 104.04 | 85.133 (4), 72.938 (3), 75.632 (3) |
V (Å3) | 3040.5 (9) | 1330.6 | 3440.5 | 1331.01 (13) |
Z | 2 | 2 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.30 | 0.17 | 0.10 | 0.10 |
Crystal size (mm) | 0.50 × 0.30 × 0.20 | 0.75 × 0.20 × 0.10 | 0.30 × 0.20 × 0.10 | 0.30 × 0.20 × 0.10 |
Data collection | ||||
Diffractometer | ? | ? | ? | ? |
Absorption correction | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication | Multi-scan Jacobson, R. (1998) Private communication | Analytical Bruker, AXS, 2008 |
Tmin, Tmax | 0.696, 1.000 | 0.732, 1.000 | 0.724, 1.000 | 0.976, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31942, 13902, 9440 | 14146, 6078, 3677 | 35694, 15699, 7254 | 20837, 5395, 3891 |
Rint | 0.064 | 0.060 | 0.096 | 0.050 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 | 0.649 | 0.625 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.188, 1.03 | 0.068, 0.202, 1.04 | 0.080, 0.213, 1.02 | 0.050, 0.140, 1.04 |
No. of reflections | 13902 | 6078 | 15699 | 5395 |
No. of parameters | 896 | 439 | 1037 | 426 |
No. of restraints | 0 | 1 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0877P)2 + 2.2248P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.095P)2 + 0.4836P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0849P)2] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0633P)2 + 0.583P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.87, −0.68 | 0.64, −0.25 | 0.68, −0.67 | 0.57, −0.33 |
Absolute structure | ? | ? | ? | ? |
Absolute structure parameter | ? | ? | ? | ? |
Computer programs: SHELXL2013 (Sheldrick, 2013).
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4 | 0.95 | 2.25 | 2.905 (3) | 125.1 |
C20—H20···O2i | 0.95 | 2.47 | 3.325 (3) | 150.1 |
C16—H16···O8ii | 0.95 | 2.32 | 3.202 (4) | 155.0 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4 | 0.95 | 2.28 | 2.8884 (18) | 121.1 |
C28—H28···O5i | 0.95 | 2.52 | 3.339 (2) | 144.6 |
C37—H37···O3ii | 0.95 | 2.41 | 3.014 (2) | 121.4 |
C38—H38···O6iii | 0.95 | 2.61 | 3.364 (2) | 136.6 |
O6—H6O···N1iv | 0.96 (2) | 1.80 (2) | 2.7588 (17) | 173 (2) |
O5—H5O···N3v | 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···N4ii | 0.91 (3) | 1.81 (3) | 2.6920 (17) | 162 (2) |
O1—H1O···N2vi | 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. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N1i | 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···O5ii | 0.85 (3) | 1.90 (3) | 2.690 (2) | 153 (3) |
O5—H5O···O2iii | 0.97 (4) | 1.95 (4) | 2.797 (2) | 144 (3) |
O6—H6O···N2iv | 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···N1i | 0.95 | 2.59 | 3.287 (3) | 130.7 |
C11—H11···O4 | 0.95 | 2.15 | 2.821 (3) | 126.5 |
C20—H20···O3v | 0.95 | 2.58 | 3.294 (3) | 131.9 |
C24—H24···O4vi | 0.95 | 2.64 | 3.521 (3) | 154.1 |
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. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O8i | 0.95 | 2.49 | 3.267 (6) | 139.2 |
C11—H11···O4 | 0.95 | 2.24 | 2.895 (5) | 125.5 |
C4—H4···O5ii | 0.95 | 2.66 | 3.365 (5) | 131.7 |
C21—H21···O2iii | 0.95 | 2.55 | 3.404 (6) | 149.3 |
C16—H16···O6iv | 0.95 | 2.61 | 3.388 (6) | 139.6 |
O1—H1O···N4i | 0.92 (7) | 1.77 (7) | 2.684 (5) | 175 (6) |
O5—H5O···O1v | 0.89 (6) | 1.94 (6) | 2.757 (4) | 153 (5) |
O5—H5O···O6 | 0.89 (6) | 2.25 (6) | 2.727 (4) | 114 (5) |
O2—H2O···O3 | 0.82 (7) | 1.89 (7) | 2.638 (4) | 152 (7) |
O6—H6O···N1vi | 0.92 (7) | 1.80 (7) | 2.719 (5) | 175 (6) |
O4—H4O···O3vii | 0.96 (6) | 1.82 (6) | 2.728 (4) | 157 (5) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y, z−1; (iii) x, y+1, z+1; (iv) −x+2, −y+1, −z+1; (v) x, y, z+1; (vi) x−1, y, z; (vii) −x+2, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4 | 0.95 | 2.20 | 2.873 (5) | 127.3 |
C20—H20···O2i | 0.95 | 2.55 | 3.263 (6) | 131.9 |
Symmetry code: (i) −x, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4 | 0.95 | 2.11 | 2.7761 (18) | 126.1 |
C14—H14···N1 | 0.95 | 2.54 | 3.4641 (18) | 165.3 |
C20—H20···O3i | 0.95 | 2.46 | 3.3386 (18) | 154.0 |
C17—H17···O6 | 0.95 | 2.63 | 3.463 (2) | 147.1 |
O5—H5O···N7 | 0.92 (2) | 1.99 (2) | 2.9068 (16) | 173.9 (18) |
O4—H4O···N5 | 0.86 (2) | 1.91 (2) | 2.6998 (15) | 152 (2) |
O6—H6O···O8 | 0.89 (2) | 1.76 (2) | 2.6123 (18) | 160 (2) |
O2—H2O···O3 | 0.90 (2) | 1.80 (2) | 2.6281 (15) | 152 (2) |
O1—H1O···N4ii | 0.89 (2) | 1.90 (2) | 2.7694 (16) | 164.6 (19) |
O8—H8O···N6iii | 0.85 (2) | 1.96 (2) | 2.8113 (18) | 177 (2) |
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4 | 0.93 | 2.14 | 2.810 (2) | 128.2 |
C28—H28···O3i | 0.93 | 2.29 | 3.134 (2) | 150.8 |
O1—H1O···N5 | 0.94 (3) | 1.81 (3) | 2.7363 (19) | 170 (2) |
O5—H5O···N12ii | 0.95 (3) | 1.92 (3) | 2.861 (2) | 172 (2) |
O4—H4O···N11iii | 0.85 (3) | 2.06 (3) | 2.850 (2) | 154 (2) |
O2—H2O···O3 | 0.86 (2) | 1.78 (2) | 2.5940 (18) | 155 (2) |
O6—H6O···O8 | 0.89 (3) | 1.83 (3) | 2.715 (2) | 174 (3) |
Symmetry codes: (i) x−1, y, z−1; (ii) x, y+1, z+1; (iii) −x+3, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···S2 | 0.95 | 2.75 | 3.557 (3) | 143.9 |
C19—H19···O12i | 0.95 | 2.48 | 3.367 (4) | 155.9 |
C26—H26···O11 | 0.95 | 2.27 | 2.907 (4) | 123.5 |
C11—H11···O4 | 0.95 | 2.22 | 2.862 (4) | 123.5 |
C4—H4···O5ii | 0.95 | 2.47 | 3.342 (4) | 153.4 |
C69—H69···O3iii | 0.95 | 2.61 | 3.152 (5) | 116.7 |
C34—H34···S1 | 0.95 | 2.97 | 3.905 (4) | 166.3 |
C37—H37···S4iv | 0.95 | 2.93 | 3.847 (4) | 161.8 |
C41—H41···O10 | 0.95 | 2.47 | 3.102 (4) | 124.1 |
C41—H41···S6v | 0.95 | 2.87 | 3.626 (4) | 137.4 |
C48—H48···O2vi | 0.95 | 2.52 | 3.050 (5) | 115.7 |
O11—H11O···O10 | 0.80 (4) | 2.34 (4) | 2.721 (3) | 110 (3) |
O11—H11O···N3 | 0.80 (4) | 2.08 (4) | 2.841 (4) | 159 (4) |
O12—H12O···N6vii | 0.88 (4) | 1.83 (4) | 2.703 (3) | 175 (4) |
O5—H5O···N4viii | 0.87 (4) | 1.86 (5) | 2.732 (4) | 175 (4) |
O4—H4O···N5 | 0.83 (5) | 1.88 (5) | 2.680 (3) | 162 (5) |
O13—H13O···O8ii | 0.76 (5) | 2.17 (5) | 2.807 (3) | 143 (5) |
O13—H13O···O12 | 0.76 (5) | 2.34 (5) | 2.711 (3) | 112 (4) |
O8—H8O···N2ix | 0.76 (5) | 1.96 (5) | 2.693 (3) | 162 (5) |
O9—H9O···O10 | 0.93 (5) | 1.78 (5) | 2.638 (3) | 152 (5) |
O2—H2O···O3 | 0.81 (7) | 1.84 (8) | 2.608 (4) | 157 (8) |
O6—H6O···O1i | 0.93 (5) | 2.03 (5) | 2.794 (3) | 139 (4) |
O6—H6O···O5 | 0.93 (5) | 2.22 (5) | 2.710 (3) | 112 (3) |
O1—H1O···N1x | 0.76 (5) | 1.92 (5) | 2.672 (3) | 167 (5) |
C14—H14···S2 | 0.95 | 2.75 | 3.557 (3) | 143.9 |
C19—H19···O12i | 0.95 | 2.48 | 3.367 (4) | 155.9 |
C26—H26···O11 | 0.95 | 2.27 | 2.907 (4) | 123.5 |
C11—H11···O4 | 0.95 | 2.22 | 2.862 (4) | 123.5 |
C4—H4···O5ii | 0.95 | 2.47 | 3.342 (4) | 153.4 |
C69—H69···O3iii | 0.95 | 2.61 | 3.152 (5) | 116.7 |
C34—H34···S1 | 0.95 | 2.97 | 3.905 (4) | 166.3 |
C37—H37···S4iv | 0.95 | 2.93 | 3.847 (4) | 161.8 |
C41—H41···O10 | 0.95 | 2.47 | 3.102 (4) | 124.1 |
C41—H41···S6v | 0.95 | 2.87 | 3.626 (4) | 137.4 |
C48—H48···O2vi | 0.95 | 2.52 | 3.050 (5) | 115.7 |
O11—H11O···O10 | 0.80 (4) | 2.34 (4) | 2.721 (3) | 110 (3) |
O11—H11O···N3 | 0.80 (4) | 2.08 (4) | 2.841 (4) | 159 (4) |
O12—H12O···N6vii | 0.88 (4) | 1.83 (4) | 2.703 (3) | 175 (4) |
O5—H5O···N4viii | 0.87 (4) | 1.86 (5) | 2.732 (4) | 175 (4) |
O4—H4O···N5 | 0.83 (5) | 1.88 (5) | 2.680 (3) | 162 (5) |
O13—H13O···O8ii | 0.76 (5) | 2.17 (5) | 2.807 (3) | 143 (5) |
O13—H13O···O12 | 0.76 (5) | 2.34 (5) | 2.711 (3) | 112 (4) |
O8—H8O···N2ix | 0.76 (5) | 1.96 (5) | 2.693 (3) | 162 (5) |
O9—H9O···O10 | 0.93 (5) | 1.78 (5) | 2.638 (3) | 152 (5) |
O2—H2O···O3 | 0.81 (7) | 1.84 (8) | 2.608 (4) | 157 (8) |
O6—H6O···O1i | 0.93 (5) | 2.03 (5) | 2.794 (3) | 139 (4) |
O6—H6O···O5 | 0.93 (5) | 2.22 (5) | 2.710 (3) | 112 (3) |
O1—H1O···N1x | 0.76 (5) | 1.92 (5) | 2.672 (3) | 167 (5) |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x, −y, −z+1; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+1, −z; (vi) x+1, y+1, z−1; (vii) x+1, y, z−1; (viii) x−1, y, z+1; (ix) −x, −y+1, −z+1; (x) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4 | 0.95 | 2.24 | 2.896 (3) | 125.2 |
C16—H16···S1B | 0.95 | 2.97 | 3.882 (6) | 161.5 |
C20—H20···O2i | 0.95 | 2.48 | 3.343 (4) | 151.1 |
C26—H26···O6ii | 0.95 | 2.66 | 3.367 (4) | 131.8 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O6i | 0.95 | 2.38 | 3.138 (2) | 136.8 |
C22—H22···O3ii | 0.95 | 2.64 | 3.309 (3) | 127.8 |
O2—H2O···O3 | 0.99 (3) | 1.78 (3) | 2.658 (2) | 145 (3) |
O6—H6O···O1i | 0.89 (3) | 2.24 (3) | 2.872 (2) | 128 (3) |
O6—H6O···O5 | 0.89 (3) | 2.26 (3) | 2.716 (2) | 112 (2) |
O1—H1O···N2iii | 0.96 (3) | 1.74 (3) | 2.692 (2) | 169 (3) |
O5—H5O···N1 | 0.95 (3) | 1.75 (3) | 2.691 (2) | 172 (3) |
O4—H4O···O3iv | 1.08 (4) | 1.80 (4) | 2.731 (2) | 141 (3) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y, z−1; (iii) x, y−1, z+1; (iv) −x, −y+1, −z+2. |
Footnotes
1Crystal structures which are neither porous nor helical are considered to be non-porous.
Acknowledgements
We thank Dr Tejender S. Thakur for the helpful discussions pertaining to the computational work. R. Dubey thanks the Indian Institute of Science for a senior research fellowship and G. R. Desiraju thanks the DST for the award of a J. C. Bose fellowship.
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