Accurate and efficient representation of intra­molecular energy in ab initio generation of crystal structures. I. Adaptive local approximate models

The global search stage of crystal structure prediction (CSP) methods requires a fine balance between accuracy and computational cost, particularly for the study of large flexible molecules. A major improvement in the accuracy and cost of the intramolecular energy function used in the CrystalPredictor II [Habgood et al. (2015). J. Chem. Theory Comput. 11, 1957–1969] program is presented, where the most efficient use of computational effort is ensured via the use of adaptive local approximate model (LAM) placement. The entire search space of the relevant molecule's conformations is initially evaluated using a coarse, low accuracy grid. Additional LAM points are then placed at appropriate points determined via an automated process, aiming to minimize the computational effort expended in high-energy regions whilst maximizing the accuracy in low-energy regions. As the size, complexity and flexibility of molecules increase, the reduction in computational cost becomes marked. This improvement is illustrated with energy calculations for benzoic acid and the ROY molecule, and a CSP study of molecule (XXVI) from the sixth blind test [Reilly et al. (2016). Acta Cryst. B72, 439–459], which is challenging due to its size and flexibility. Its known experimental form is successfully predicted as the global minimum. The computational cost of the study is tractable without the need to make unphysical simplifying assumptions.

1. Introduction

The primary aim of crystal structure prediction (CSP) techniques is to produce a ranked list of all the potential crystal structures for a molecule or set of molecules. Because of the significant effect that crystal structure has on solid-state properties, such as colour, solubility and hygroscopicity, such a ranked list offers a wealth of information and many opportunities to improve the development of new crystalline materials (Price et al., 2016; Neumann et al., 2015). In the case of the pharmaceutical industry, the appearance of a new or unexpected form or polymorph can have major legal and economic ramifications, particularly if solubility/bioavailability are affected, as illustrated by the cases of the appearance of Ritonavir form II (Chemburkar et al., 2000) and the Zantac litigation (Seddon, 1999). Furthermore, the ability to tune a molecule's solid-state properties through predictive approaches would be very useful to industries that rely on crystalline materials. Therefore, significant benefits are offered by the possibility of predicting a molecule's crystal structure(s), especially when this is possible via ab initio techniques that rely only on molecular structure information.

Whilst a relatively new field, CSP methods for organic molecules have undergone considerable improvements over the past few years, as seen in the increasing size and complexity of molecular targets in the blind tests organized by the Cambridge Crystallographic Data Centre, as well as the increasing level of success achieved in the tests (Day et al., 2005, 2009; Bardwell et al., 2011; Motherwell et al., 2002; Lommerse et al., 2000). The targets that CSP groups are being asked to investigate as a matter of routine are becoming more industrially relevant, with larger, more flexible molecules that could be seen as drug analogues now being considered. Indeed, in the case of molecule (XXIII) in the sixth blind test (Reilly et al., 2016), the target represents a former drug candidate for the treatment of Alzheimer's disease. All the targets were chosen so as to present challenges that test the theories and computational capabilities currently available.

1.1. Global search in CSP

The central tenet of CSP is that the crystal structures that are most likely to form will be low-energy minima on the free-energy surface, with respect to structural variables, namely: cell lengths and angles, the molecular position and orientation, and the molecule's internal degrees of freedom (Pantelides et al., 2014; Brandenburg & Grimme, 2014; Woodley & Catlow, 2008; Price, 2008; Cruz-Cabeza et al., 2015). Thermodynamically, the most stable crystal structure (at given temperature and pressure) is the global minimum on the Gibbs free-energy surface; however, given the cost inherent in free-energy calculations and the comparatively small energetic contributions arising from entropic effects, most CSP methods use lattice energy/enthalpy rather than free energy in order to rank the predicted crystal structures.

A major factor in successfully identifying all likely polymorphs is the trade-off made between the accuracy of the model used to describe the differences in energy between a molecule's possible structures (often less than 5 kJ mol⁻¹), and the extent of the search for low-energy minima across the entire free-energy surface. In view of this, most CSP techniques use a broadly two-stage methodology: a first-stage global search that is used to search for low-energy structures on the lattice energy surface using a relatively low-cost, less accurate lattice energy model; and a second-stage refinement that takes the most promising structures from the first stage and re-ranks them via local energy minimization, using a more accurate and computationally demanding lattice energy model. All the successful predictions in the sixth blind test (Reilly et al., 2016) used some variant of this multi-stage methodology.

In order to identify all potential low-energy polymorphs, the first stage must perform an extensive search (typically involving hundred of thousands of points) of the lattice energy surface over sufficiently wide ranges of the lattice energy model variables (cell lengths and angles, conformational degrees of freedom etc.); therefore, the efficiency of the lattice energy model is very important. Moreover, since only a relatively small proportion (typically a few hundreds) of the lowest-energy structures identified will be passed for refinement to the second stage, the lattice energy model employed by the first stage also needs to be sufficiently accurate not to exclude any potential polymorphs from further consideration.

Overall, achieving the right trade-off between the efficiency and accuracy of the first-stage lattice energy model is a key challenge for CSP. If the accuracy of the lattice energy model can be increased at moderate computational cost, the risk of missing low-energy structures can be decreased. Furthermore, the cost of the second stage can be reduced significantly as increased confidence in the ranked list of structures generated in the first stage typically allows a decrease in the number of structures that must be taken through to the computationally intensive refinement stage, opening the possibility for the latter to employ even higher-accuracy lattice energy models.

This paper focuses on significantly improving the efficiency of the global search stage via improvements to the CrystalPredictor algorithm (Karamertzanis & Pantelides, 2007, 2005; Habgood et al., 2015), which has been used extensively in blind tests and in a variety of CSP applications (see, for example, Bardwell et al., 2011; Day et al., 2009; Braun et al., 2013, 2014, 2016; Vasileiadis et al., 2012; Eddleston et al., 2015; Uzoh et al., 2012).

Before describing specific advances, we give a brief overview of the algorithm to the extent necessary for the purposes of this paper.

1.2. The CrystalPredictor algorithm

The CrystalPredictor algorithm (Karamertzanis & Pantelides, 2007, 2005; Habgood et al., 2015) is a global search algorithm based on a large number of gradient-based local minimizations starting from crystal structures generated by a Sobol sequence (Sobol, 1967), a low-discrepancy technique that ensures the best coverage of the space of the variables that uniquely define a crystal structure.

The original version of the algorithm CrystalPredictor I (Karamertzanis & Pantelides, 2007, 2005) was used successfully in several CSP studies to produce initial ranked lists of crystal structures. However, in order to ensure that all experimentally known structures are identified by the CSP, it was often found to be necessary to refine the 1000 to 1500 lowest-energy structures in these initial lists, which resulted in very significant computational costs (see, for example, Vasileiadis et al., 2012, 2015).

The above issue with CrystalPredictor I was partly caused by the insufficiently accurate description of the effects of molecular conformation on both the intramolecular and intermolecular contributions to the lattice energy. This realisation led to an improved version of the algorithm, CrystalPredictor II (Habgood et al., 2015), using a more accurate energy function that utilizes local approximate models (LAMs; Kazantsev et al., 2010). LAMs allow the efficient and accurate calculation of intramolecular energy as a function of flexible torsion angles (`independent' conformational degrees of freedom, ). Moreover, LAMs also allow the values of those degrees of freedom that are not explicitly treated as flexible in the minimization (the `dependent' degrees of freedom, , including bond lengths, bond angles and any torsion angles that are not included in ) to be determined as functions of the independent conformational degrees of freedom, .

CrystalPredictor assumes that the lattice energy of a crystal is given as a function of the cell lengths and angles, collectively denoted as X, as well as the positions and orientations of the molecules in the asymmetric unit, collectively denoted as β, and the molecules' independent conformational degrees of freedom, . The optimization then seeks to minimize a lattice energy function, U^latt of the form

where the intermolecular energy is separated into (a) an electrostatic term, , evaluated by the Coulombic attraction between atom centres, based on point charges obtained using isolated molecule ab initio calculations, and (b) a repulsion/dispersion term, , described by Buckingham potentials whose parameters have been fitted to experimental data, typically the FIT potential (Cox et al., 1981; Williams, 1984; Coombes et al., 1996). We note that both U^e and U^rd are functions of molecular conformation as it affects intermolecular distances. In general, the electronic charge distribution within the molecule is also a function of molecular conformation, and therefore the atomic charges used in U^e may also depend on .

The intramolecular energy contribution, is given by

where is the intramolecular energy of an isolated molecule at conformation and U^gas is the minimum energy of the unconstrained isolated molecule (i.e. in vacuo, with all internal degrees of freedom allowed to vary). To avoid expensive repeated ab initio calculations for the evaluation of the terms and U^e during the global search, a set of reference calculations at values of the on a regular grid are performed before the start of the global search, and are subsequently used in CrystalPredictor to obtain a low-cost approximation of these energies at any point. The two versions of CrystalPredictor differ in how the approximation is constructed. In CrystalPredictor II, the intramolecular energy at some value of the independent conformational degrees of freedom is calculated from the LAM with the closest matching conformation, , on the grid using an approximation of the form

whilst the set of dependent degrees of freedom is obtained by a linear approximation of the form

where the matrices A and C and the vector b are given by (Kazantsev et al., 2011)

The variation of point charges with conformation is neglected in CrystalPredictor II, so that the point charges used to evaluate are taken as those at , i.e. = .

The global search domain in terms of independent conformational degrees of freedom can be denoted as , where n is the total number of independent conformational degrees of freedom and and , , are selected to include all areas of practical interest, typically where is below 20 to 30 kJ mol⁻¹. LAMs are calculated at grid points whose location depends on the size of the search domain and a user-specified grid spacing . The conformational space is therefore partitioned into hyper-rectangles of the form

The LAM validity range, , needs to be small enough to ensure that expressions (3) and (4) provide sufficiently good approximations for the intramolecular energy and dependent degrees of freedom within a certain conformational distance from .

The adoption of a regular LAM grid has been found to be effective in CSP for several molecules, such as β-D-glucose, ROY and a pharmaceutical compound, BMS-488043 (Habgood et al., 2015). However, the number of LAM points needed to achieve a desired coverage grows exponentially with the number of degrees of freedom. For highly flexible molecules, where the number of independent conformational degrees of freedom is large, and the range of flexibility, [, ], to be searched is wide, the number of LAMs to be calculated incurs a high computational cost. In such cases, the choice of an appropriate has a significant impact on both the accuracy and computational cost, and its determination requires substantial analysis of the molecule of interest prior to computing the grid points.

1.3. Aims

In this paper we propose improvements to the algorithm that address the issues identified above, leading to reduced computational cost and improved accuracy. In particular, we seek to achieve this by introducing an adaptive LAM implementation so that the LAM points no longer need to be placed on a regular grid.

A motivating example for the development of an improved algorithm is introduced in §2, based on molecule (XXVI) from the sixth blind test (Reilly et al., 2016). The adaptive LAM placement algorithm is described in §3, and the reduction in computational cost that it offers is analysed. Finally, in §4, we revisit the motivating example, applying to it the improved CrystalPredictor II algorithm in the context of a complete CSP study of molecule (XXVI) from the sixth blind test.

2. Motivating example: molecule (XXVI) of the sixth blind test

The recent blind test on crystal structure prediction methods, organized by the Cambridge Crystallographic Data Centre, sought to evaluate the capabilities of current computational methods in predicting the crystal structures of organic molecules. Five targets were chosen, representing challenges to the crystal structure prediction community. The two versions of CrystalPredictor were deployed by two of the participating groups, in combination with CrystalOptimizer, to identify Z′ = 1 structures. This approach resulted in the identification of the known experimental structures within the predicted energy landscapes in most cases. However, in the case of molecule (XXVI), shown in Fig. 1, the multiple flexible torsion angles present particular difficulties, which are discussed here and motivate the development of an improved version of CrystalPredictor II.

Figure 1 Molecular diagram of molecule (XXVI) and independent degrees of freedom.

Molecule (XXVI) contains the common 1,1′-binaphthalene fragment, which can feature axial chirality, although no chiral precursors were present in the synthesis. As reported by Reilly et al. (2016), there are currently two known pure experimental forms: form (1) is a Z′ = 1 structure crystallized in the space group, while form (11) is a structure discovered through polymorph screening by Johnson Matthey (Pharmorphix), after the conclusion of the blind test, for which no structural data are currently available. In addition, there are nine reported solvates. Unusually for 1,1′-binaphthalene-based molecules, one O atom is unsatisfied in terms of hydrogen bonds, and the angles and torsions in the amide group and phenyl rings are somewhat outside expected ranges. This is a result of the bulkiness of the 1,1′-binaphthalene and phenyl groups, as well as the internal hydrogen bond occurring between the chlorine in one half of the molecule, and the amide group in the opposite half. The number and unusual values of the independent degrees of freedom, as well as its sheer size, contribute to the difficulties posed by this molecule.

In the sixth blind test (Reilly et al., 2016), the use of CrystalPredictor I and CrystalOptimizer by the Price et al. group successfully led to the identification of form (1) as the lowest energy structure in the final landscape. The use of CrystalPredictor I, however, required making severe assumptions on flexibility to limit the computational cost; as is usually done with CrystalPredictor I when there are many flexible degrees of freedom, the flexible torsion angles were divided into three groups (group 1 containing T1, group 2 containing T3–5, and group 3 containing T7). This approach has been successful in other investigations (Vasileiadis et al., 2012) and relies on the assumption that flexible torsions in distinct parts of the molecule can rotate independently, with their effect on being largely unaffected by the values of the flexible torsions in the other torsion groups. However, in the case of molecule (XXVI), since the benzene groups that rotate in the different halves of the molecule are in close proximity to each other, such an assumption may not be fully justified in this case. The loss of accuracy arising from this treatment was acknowledged by the Price et al. team and was countered by applying the second-stage refinement to a wider than usual range of the low-energy crystal structures predicted in the CrystalPredictor I landscape. More specifically, a single iteration of CrystalOptimizer was applied to each of the 9400 structures identified by CrystalPredictor I within 40 kJ mol⁻¹ of the global minimum, thereby resulting in re-ranking of the structures. The full CrystalOptimizer calculation was then performed for the 1322 lowest-energy structures. Although in this case the experimental form was successfully identified, this decomposition approach is not generally applicable to all molecules, and a more accurate method of covering the conformational space is needed (see Habgood et al., 2015) for a more complete discussion).

Our research group's submission for molecule (XXVI) made use of CrystalPredictor II, with all seven torsional angles shown in Fig. 1 being treated as independent degrees of freedom, . The domain of each angle that was deemed to be relevant for CSP purposes was initially decided by analysis of crystal structures in the Cambridge Structure Database (CSD) and the results of one-dimensional scans through each independent degree of freedom. A LAM validity range of ±15° was used for all torsional angles, resulting in a grid comprising 2592 LAM points (see Table 1). The computation of the latter at the HF/6-31G(d,p) level of theory required approximately 200 000 CPU h [typically on Intel(R) Xeon(R) CPU E5-2660 v2 running at 2.20 GHz].

Table 1
Independent conformational degrees of freedom considered for molecule (XXVI) by our group during the sixth blind test

The experimental values are the reported values of the torsions in form (1) (Reilly et al., 2016) and were not available to us during the blind test. The bold experimental value indicates that this torsion lies outside the specified search space.

Independent degree of	LAM regular grid			Experimental value in form (1) (°)
freedom, (cf. Fig. 1)	Search domain (°)	Spacing Δθ (°)	No. of grid points	(not available during the blind test)
T1	[0, 360]	±15	12	215.76
T2	[165, 195]	±15	1	181.26
T3	[95, 185]	±15	3	163.34
T4	[55, 115]	±15	2	78.47
T5	[95, 185]	±15	3	222.46
T6	[165, 195]	±15	1	185.06
T7	[0, 360]	±15	12	301.872

Our normal practice in the applications of CrystalPredictor II is to also evaluate the intramolecular energies at the edges of the search space; if these are found to be lower than a user-specified threshold (typically 20–30 kJ mol⁻¹), the search space is expanded. In the case of molecule (XXVI), this investigation identified energies lower than 10 kJ mol⁻¹ on the boundaries of the domains for torsions T3 and T5, and therefore these domains would normally have to be expanded quite significantly. However, a larger regular grid with the domain of the two key torsions extended by the necessary 120° would involve 11 858 LAMs, and their construction would require approximately 910 000 CPU h. As this was impracticable within the time constraints of the blind test, it was decided not to extend the search beyond the domains indicated in Table 1.

As indicated in Table 1, the experimental value for the torsion angle T5 is 222.46°, which unfortunately lies outside the search domain [95°, 185°]. As a result, our search failed to identify form (1) of molecule (XXVI). This illustrates the importance of developing new techniques that would allow large conformational spaces to be covered efficiently by LAMs, which in turn provides the motivation for the present work.

3. An algorithm for adaptive LAM placement

This section presents an adaptive algorithm that automatically positions LAMs at points in the search domain of the independent degrees of freedom, where necessary to ensure the required degree of accuracy. Firstly, the revised algorithm for generating new LAMs is summarized in §3.1, with examples of its implementation given in §§3.2 and 3.3.

3.1. Adaptive generation of LAMs

The basic idea of the adaptive LAM placement algorithm proposed in this paper is to take an existing set of LAMs placed over the search domain of the independent conformational degrees of freedom , and to try to identify a point at which these LAMs may not attain the required accuracy. If such a point is found, then a new LAM is then generated at that point. The procedure is repeated until no new point is found to be necessary.

Establishing the exact error of the approximation provided by a LAM at a particular point would require performing the corresponding quantum mechanical calculation and comparing its results with the LAM predictions. As this would defeat the purpose of an efficient LAM placement algorithm, we choose to use an approximate criterion based on the difference in the predictions at a point between two neighbouring LAMs.

In particular, we assume that the maximum discrepancy between the predictions of two LAMs generated at points . and . respectively, is likely to occur around the mid-point . Using equation (3), we can then easily compute the quantities using the two LAMs. If we denote these by and , then a new LAM is generated at point only if these quantities differ by more than a certain specified threshold, , in absolute value, i.e.

However, before deciding whether to generate a new LAM at M, there are two additional conditions we need to consider. First, it is unnecessary to generate a LAM at point M if the latter is unlikely to be inside the region which would be relevant for the purposes of CSP, i.e. if exceeds a given threshold, . Of course, the exact value of is not known, but it can be approximated by the values obtained by the two LAMs. Conservatively, we choose to consider the lower of these two values; therefore, another necessary criterion for a LAM to be generated at point M is

A second consideration that needs to be taken into account is that the above reasoning is valid only if the LAMs A and B are indeed those nearest to point M. If there exists a third LAM C which is nearer to M than either A or B, then of course the accuracy of the approximations provided by the LAMs at A and B at point M is irrelevant: neither of those would be used during the search to determine the quantity . Therefore, a third necessary criterion for a LAM to be generated at point M is

For each and every existing LAM k other than A and B, where the norm is the Euclidean norm in conformational space.

The above ideas provide the basis of the new adaptive algorithm for LAM generation. Given any set of LAMs, we consider each and every pair (A, B), determine its midpoint M, and test criteria (9)–(11). If all of those are found to be true, then a new LAM is generated at point M, and the procedure is repeated until no more new LAMs are found to be necessary.

In our current implementation, the algorithmic parameters and are set by default at 1 and 20 kJ mol⁻¹, respectively. Using a smaller value of leads to increased consistency between LAMs, but also results in the addition of a greater number of LAM points and hence higher computational cost. We have found the value of 1 kJ mol⁻¹ to give an appropriate balance between cost and consistency. The default value of is chosen based on the assessment of Thompson & Day (2014) of the maximum energetic cost of molecular distortion away from gas phase conformation in naturally occurring polymorphs. Here, using a larger value of increases the reliability of the LAMs for higher-energy conformations, but this again comes at the cost of adding more LAMs. The norm in criterion (11) is based on the Euclidean distance

The initial set of LAMs is constructed over a relatively coarse regular grid which is then subsequently refined according to the algorithm presented here, resulting in a complete set of LAMs prior to the start of the global search. A flowchart describing this process is provided in the supporting information. As in the previous implementation of CrystalPredictor II (Habgood et al., 2015), during the search, equations (3) and (4) are applied using the LAM that is nearest, in the Euclidean distance sense, to the current point .

3.2. Illustrative example 1: benzoic acid

In order to better understand the concept of adaptive LAM placement, we first consider a molecule with a single independent degree of freedom, namely benzoic acid (see Fig. 2). The chemically relevant domain for torsion angle T1 is initially covered by four LAMs based at the points T1 = −90, −30, +30 and +90°, at the M06/6-31G(d,p) level of theory.

Figure 2 Molecular diagram and degree of freedom T1 for benzoic acid, at T1 = 0.

As can be seen in Fig. 3(a), there is clearly a significant mismatch (9.2 kJ mol⁻¹) in the intramolecular energy contribution predicted by adjacent LAMs at T1 = ± 60°. This can be corrected by inserting two LAMS at these positions, as illustrated in Fig. 3(b). On the other hand, there is no such mismatch at the boundary between the original second and third LAMs at T1 = 0°, and therefore no new LAM needs to be inserted there. This consistency check, in which different LAM predictions are compared to each other, ensures that the intramolecular energy is described consistently by the LAMs at the given boundary. It does not, however, guarantee that that ab initio accuracy is achieved, although we note that LAMs have been shown to represent ab initio results very well in their locality (Kazantsev et al., 2011). In the case of a symmetric molecule such as benzoic acid, the consistency of the LAMs at T1 = 0° could be attributed to the symmetric placement of LAM points and does not imply agreement with the ab initio energy value. This could be addressed through the manual addition of LAMs by the user to break symmetry where appropriate.

Figure 3 Intramolecular energy for benzoic acid based on one-dimensional LAMs. (a) Initial regular grid and (b) final LAM placement. Crosses represent LAMs on the initial regular grid, circles LAMs added to eliminate mismatch between adjacent LAMs.

Overall, achieving the same level of accuracy with a regular grid would require a grid spacing of = ± 15°, i.e. 7 LAMs overall (starting with one based at T1 = −90°), as opposed to the 6 LAMs shown in Fig. 3(b). Whilst only a small saving is achievable in this simple case, much more marked efficiencies can be achieved for molecules involving multiple independent degrees of freedom, as illustrated by the next example.

3.3. Illustrative example 2: the ROY molecule

The adaptive algorithm is further illustrated for the ROY molecule (5-methyl-2-[(2-nitrophenyl)­amino]-3-thiophenecarbonitrile) (Yu, 2010), which is considered here to involve two independent conformational degrees of freedom, T1 and T2, as shown in Fig. 4. These two degrees of freedom have broad ranges of flexibility, with T1 and T2 , but within this overall conformational space there are large regions that are characterized by high intramolecular energy which are unlikely to be of relevance to CSP.

Figure 4 Molecular diagram and the two independent conformational degrees of freedom considered for 5-methyl-2-[(2-nitrophenyl)­amino]-3-thiophenecarbonitrile (ROY).

Starting with an initial uniform grid generated with = ±20° and comprising 20 LAMs, at the B3LYP/6-31G(d,p) level of theory, the application of the LAM generation algorithm results in the final set of 41 LAMs shown in Fig. 5(b). The minimum spacing between these LAMs is 14°; a regular grid constructed over the original domain would require about 163 LAMs to achieve the same minimum spacing ( ≃ ±7°). However, many of these LAMs would be unnecessary: for example, we note that the adaptive algorithm does not introduce any new LAM points in the region . Fig. 5(b) also shows the positions of the six known experimental forms of ROY (Yu, 2010). This demonstrates that the algorithm does indeed focus computational effort on relevant areas of conformational space.

Figure 5 LAM placements for ROY. (a) Initial regular grid (20 LAMs), with = ±20°. (b) Final LAM set (41 LAMs) derived by adaptive LAM placement algorithm. Crosses represent LAMs in the initial regular grid, circles LAMs added by adaptive placement algorithm; triangles show the positions of experimentally known conformations.

The intramolecular energy predictions by the original and final sets of LAMs are shown in Figs. 6(a) and (b), respectively. It is clear that the low conformational energy regions are not rectangular, i.e. there is significant interaction between the two torsional angles. It can also be seen that the adaptive LAM placement leads to a smoother intramolecular energy surface in these key regions.

Figure 6 Intramolecular energy (in kJ mol^−1) as predicted by LAMs in 0.5° scan across conformational space; (a) under a regular coarse grid (Δθ = ±20°), (b) using the adaptive LAM placement of Fig. 5(b). Crosses represent regular LAMs, circles non-uniform/adaptive LAMs and (c) Ab initio intramolecular energy based on a 5° scan.

The intramolecular energy contribution is also computed ab initio over the same range of degrees of freedom at 5° increments and shown in Fig. 6(c). Visual comparison of the three energy landscapes show that key qualitative features are captured by both LAM-based approximations. A more quantitative comparison is presented in Figs. 7(a) and (b), where the differences between the LAM approximation and the ab initio energies are computed at 5° intervals. The average absolute deviation for the regular coarse grid scheme is 0.75 kJ mol⁻¹, while for the adaptive scheme it is 0.56 kJ mol⁻¹. More importantly, it is evident that with the regular grid, there are many areas in which the error is more than 5 kJ mol⁻¹, particularly at the edges of LAM validity. This can lead to the generation of a low-accuracy energy landscape during the global search, in which some structures are found to have unrealistically low or high lattice energy. Finally, it can be seen that in the areas surrounding the experimental structures (black triangles), improved accuracy is achieved.

Figure 7 Absolute difference between ab initio and LAM predicted intramolecular energies (kJ mol^−1) based on a 5° scan, with LAMs computed based on (a) the coarse regular grid of Fig. 5(a). (b) The adaptive scheme of Fig. 5(b). The black triangles represent experimental conformations.

4. CSP investigation of molecule (XXVI)

The proposed algorithm is now applied to molecule (XXVI) from the sixth blind test (cf. §2). As shown in Fig. 1, the molecule has 7 flexible degrees of freedom, several of which have broad ranges of flexibility.

In this new CSP study, the search domains for all 7 torsion angles are extended until the intramolecular energies at the edges of the search space exceed 15 kJ mol⁻¹. While a larger cutoff value has been used in previous work (Habgood et al., 2015), 15 kJ mol⁻¹ is a practical value given the computational cost, and the low likelihood of a molecular distortion with an energetic cost greater than 15 kJ mol⁻¹ (Thompson & Day, 2014). As can be seen by a comparison of the search domains listed in Tables 1 and 2 this now results in much wider domains for T3 and T5 than those used in our original CSP study (Reilly et al., 2016).

Table 2
Search domain and initial LAM grid for CSP study on molecule (XXVI)

Independent degree of	Initial LAM grid			Experimental value in form (1) (°)
freedom, (cf. Fig. 1)	Search domain (°)	Spacing Δθ (°)	No. of grid points	(not available during the blind test)
T1	[0, 360]	±30	6	215.76
T2	[165, 195]	±15	1	181.26
T3	[20, 260]	±30	4	163.34
T4	[55, 115]	±15	2	78.47
T5	[20, 260]	±30	4	222.46
T6	[165, 195]	±15	1	185.06
T7	[0, 360]	±30	6	301.872

4.1. Generation of an appropriate LAM set

In applying the algorithm proposed in this paper, we start with a relatively coarse regular grid with increments of 60° for T1, T3, T5 and T7, and 30° for T2, T4 and T6 (see Table 2), again, at the HF/6-31G(d,p) level of theory. Overall, this initial grid requires the generation of 1152 LAMs. We then apply the adaptive LAM placement algorithm of §3 in a single-pass mode, i.e. simply considering all pairs of points in the initial grid and deciding whether to place a LAM at their mid-point. Overall, this results in the generation of an additional 2491 LAMs.

The accuracy gain achieved by the judicious placement of new LAM points is illustrated in Fig. 8 for a 30° × 30° sub-region near the experimental values of torsions T1 and T7 (indicated by a filled triangle). The figures show the differences between the value of predicted using the nearest LAM and the corresponding ab initio value. The underlying data are generated by varying T1 and T7 in 2° increments, while keeping the other 5 torsional angles constant at the values T2 = 180.0°, T3 = 170.0°, T4 = 70.0°, T5 = 230.0° and T6 = 180.0°.

Figure 8 Absolute error between ab initio and LAM predicted energies for the experimental form (1), across the validity range of the nearest LAM point on the adaptive grid to the experimental values of T1 and T7, calculated at 2° increments. The filled triangle indicates the experimental values of T1 and T7. (a) Error obtained using the initial LAM set constructed on a regular grid; the four LAMs used for these calculations are outside the domain shown at (200°, 80°), (200°, 20°), (260°, 20°) and (260°, 20°), for T1 and T7, respectively. (b) Error obtained using the final LAM set, including a new LAM point indicated by an open white circle.

Fig. 8(a) shows results obtained using the initial LAM set on a regular grid. The four nearest LAMs used for this purpose are outside the domain shown. As can be seen, the values of involve non-negligible errors, with a maximum of 5.15 kJ mol⁻¹ across the sub-region and a value of 1.01 kJ mol⁻¹ at the experimental values of T1 and T7. On the other hand, Fig. 8(b) shows results obtained with the final LAM set which now includes a new LAM placed at the position indicated by the open circle. It can clearly be seen that the addition of this single new point in this sub-region results in very substantial reduction in the error in . The maximum error across this sub-region is now 0.27 kJ mol⁻¹, with the error at the experimental values of T1 and T7 being just 0.09 kJ mol⁻¹.

As has already been noted in §2, a regular grid that would cover the entire domain of interest at the required accuracy would have to incorporate 11 858 LAMs, whose construction would require approximately 910 000 CPU h on the computing hardware used for this study. Instead, the LAM set determined by the new adaptive LAM placement algorithm requires only 3643 LAMs, an overall reduction of just under 70%.

4.2. Global search using CrystalPredictor II

A global search over 1 000 000 candidate structures is performed using CrystalPredictor II, making use of the LAM set determined above. As shown in Fig. 9, this results in 81 unique structures being identified within 10 kJ mol⁻¹ of the global minimum, with 465 and 1413 unique structures being identified within, respectively, 20 and 30 kJ mol⁻¹. The experimental form is identified as the 130th lowest energy structure, with a lattice energy 12.27 kJ mol⁻¹ greater than the global minimum, and a good reproduction of the experimental geometry (RMSD₂₀ = 0.595 Å).

Figure 9 CrystalPredictor II energy landscape for molecule (XXVI) based on 1000 000 minimizations and adaptive LAM placement. The square denotes the experimental form, the solid line is the 10 kJ mol^−1 cut-off from the global minimum, and the heavy and light dashed lines are the 20 and 30 kJ mol^−1 cut-offs from the global minimum, respectively.

4.3. Refinement of low-energy crystal structures using CrystalOptimizer

CrystalOptimizer minimizations are performed on the 1413 unique structures that were identified within 30 kJ mol⁻¹ from the global minimum (cf. Fig. 9). The approach followed was identical to that in our original investigation carried out in the context of the sixth blind test (see supporting information in the blind test paper by Reilly et al. (2016). In particular, intramolecular energy and conformational multipoles were determined using quantum mechanical calculations at the PBE1PBE 6-31G(d,p) level of theory, and an extended set of independent conformational degrees of freedom was considered as seen in Fig. 10. The use of a different level of theory from CrystalPredictor implies that it is not possible to re-use the LAMs generated at the global search stage. If the same level of theory were used, this would result in a reduction of the number of quantum mechanical calculations at the refinement stage.

Figure 10 Independent conformational degrees of freedom used in the CrystalOptimizer investigation of molecule (XXVI). Curly arrows represent torsions, block arrows represent angles.

The resulting energy landscape is presented in Fig. 11. The experimental form is found at the global minimum, with another 17 structures having lattice energy within 10 kJ mol⁻¹ from the global minimum, and 92 within 20 kJ mol⁻¹. We note that these numbers are significantly lower than the corresponding numbers of structures determined at the end of the global search (81 and 465, respectively); thus, refinement using a more accurate lattice energy model and taking account of a higher degree of conformational flexibility has resulted in substantial clarification of the polymorphic landscape. We also note that the geometry of the experimental structure is reproduced with good accuracy (RMSD₂₀ = 0.330 Å), as illustrated in Fig. 12 and Table 3.

Table 3
Structural information for the predicted crystal structure for molecule (XXVI)

Molecule (XXVI)	ρ (g cm^−3)	a (Å)	b (Å)	c (Å)	α (°)	β (°)	γ (°)	Rank	U^latt (kJ mol^−1)	RMSD20 (Å)
Experimental	1.332	10.40	11.03	14.18	76.83	73.33	63.47	–	–	–
CrystalPredictor II	1.332	10.23	10.74	14.95	89.14	72.42	64.02	130	−193.41	0.60
CrystalOptimizer	1.337	10.31	11.25	14.10	79.81	73.97	62.88	1	−212.59	0.33

Figure 11 Lattice energy landscape following CrystalOptimizer results for molecule (XXVI). The structures generated following the refinement of the 1413 structures generated by the global search stage within 30 kJ mol^−1 of the lowest-energy structure are shown. The lowest 100 unique structures span a lattice energy range of 20.8 kJ mol^−1 from the global minimum, whilst only 17 unique structures are identified with lattice energies within 10 kJ mol^−1 of the global minimum. The square denotes the experimental form, the solid line is the 10 kJ mol^−1 cut-off from the global minimum, and the heavy and light dashed lines are the 20 and 30 kJ mol^−1 cut-offs from the global minimum, respectively.

Figure 12 Overlay of the global minimum predicted structure (green tubes) generated in the CrystalOptimizer energy landscape, and the experimental structure (grey tubes = C atoms, red = O, blue = N, white = H).

The computational cost of the CSP study is summarized in Table 4. The generation of LAM points remains the most significant cost but is now tractable given the high-dimensionality of this molecule.

Table 4
Computational cost of CSP for molecule (XXVI)

Step	No. of calculations	CPU h (approximate)
Step 0: construction of LAM regular grid	3643	280 000
Step 1: CrystalPredictor II minimizations	1 000 000	20 000
Step 2: CrystalOptimizer refinements	1413	80 000
Total	–	380 000

5. Concluding remarks

The 2016 blind test (Reilly et al., 2016) revealed that achieving an appropriate balance between computational cost and accuracy in the global search for crystal structures remains a challenge for large molecules. The algorithm presented in this paper addresses this issue by introducing the adaptive placement of LAMs within the CrystalPredictor II algorithm, an improvement on the uniform grid scheme which had proved too computationally demanding to apply to molecule (XXVI). A higher density of LAM points is automatically achieved in chemically interesting areas of conformational space, thereby resulting in a more efficient use of expensive ab initio calculations. This, in turn, allows the CrystalPredictor II algorithm to handle larger molecules and to explore larger areas of conformational space, through an effective global search methodology. The successful application of this new approach to molecule (XXVI) realises one of the aims of the blind tests, namely to drive innovation in CSP by providing unique and challenging molecular systems.

Throughout the CrystalPredictor II calculations, the lattice energy for any given molecular conformation is computed by making use of the LAM that is nearest to . One undesirable effect of this approach is that discontinuities in both the lattice energy and its partial derivatives may occur at points that lie on the boundaries between adjacent LAMs. Such discontinuities may cause numerical difficulties for CrystalPredictor's gradient-based optimization algorithm in cases in which the path of the optimization iterations crosses one or more LAM boundaries. In practical terms, this is usually exhibited by the algorithm reaching a point from which it cannot achieve any further reduction in lattice energy, despite the fact that the mathematical optimality conditions are not yet strictly satisfied. In the calculations reported in this paper and in our previous work, we have chosen to adopt a conservative approach whereby such points are still considered as candidates for further refinement. However, this may result in much additional computation: for example, in the case of molecule (XXVI), 1283 of the 1413 structures that underwent final refinement (cf. §4.3) actually belonged to this category. Part II of this paper (Sugden & Adjiman, 2016) is concerned with addressing this problem in a more fundamental manner by removing the discontinuities at the LAM boundaries.

Data statement: Data underlying this article can be accessed on Zenodo at https://doi.org/10.5281/zenodo.56731, and used under the Creative Commons Attribution licence.

Supporting information

Computing details

(1)

Crystal data

Triclinic, P1	α = 106.0°
a = 11.3 Å	β = 62.6°
b = 14.1 Å	γ = 94.4°
c = 10.3 Å	V = 1396.26 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.934243	0.897893	0.620263
C2	0.945564	0.851544	0.47678
C3	0.868023	0.887593	0.426574
C4	0.778071	0.970413	0.515663
C5	0.767479	1.01499	0.660341
C6	0.844772	0.979215	0.712103
C7	0.700765	0.995013	0.440825
C8	0.590377	1.13428	0.423181
C9	0.542928	1.23296	0.494027
C10	0.472159	1.27926	0.441249
C11	0.45227	1.22423	0.31478
C12	0.504323	1.12497	0.244922
C13	0.571651	1.08043	0.296199
C14	0.420298	1.37898	0.510323
C15	0.352053	1.42123	0.457077
C16	0.332417	1.36659	0.331997
C17	0.381774	1.2701	0.262519
C18	0.568263	1.28982	0.623161
C19	0.468607	1.30913	0.771774
C20	0.494126	1.36294	0.893849
C21	0.6182	1.3959	0.867183
C22	0.724047	1.37755	0.717613
C23	0.698968	1.32395	0.594338
C24	0.853091	1.41139	0.687753
C25	0.954073	1.3939	0.541756
C26	0.929316	1.34194	0.41937
C27	0.805179	1.30784	0.444788
C28	0.225415	1.33386	0.908244
C29	0.095290	1.28449	0.946432
C30	0.064050	1.19897	0.996514
C31	−0.062893	1.16264	1.03792
C32	−0.160236	1.21156	1.02912
C33	−0.131669	1.29745	0.981151
C34	−0.005499	1.33368	0.942091
Cl1	0.654574	1.11498	0.78833
Cl2	0.180498	1.13522	1.01358
N1	0.65913	1.09172	0.479198
N2	0.339388	1.27549	0.807546
H1	−0.258834	1.18265	1.06098
H2	−0.084338	1.09659	1.07741
H3	−0.207767	1.33634	0.975274
H4	0.018241	1.40166	0.90764
H5	0.489996	1.08319	0.147936
H6	0.609726	1.00419	0.243465
H7	0.278444	1.40111	0.291081
H8	0.312935	1.49759	0.511738
H9	0.367524	1.2272	0.165986
H10	0.434534	1.42163	0.606791
H11	0.413155	1.37746	1.00834
H12	0.636955	1.43654	0.961464
H13	0.786744	1.26869	0.349811
H14	1.009	1.32901	0.303889
H15	0.87054	1.45187	0.783095
H16	1.05268	1.4203	0.52014
H17	0.330723	1.20806	0.746737
H18	0.67471	1.13914	0.562759
H19	0.872813	0.851737	0.31656
H20	1.01446	0.787462	0.404343
H21	0.832987	1.01539	0.825163
H22	0.993969	0.870642	0.661757
O1	0.684195	0.929093	0.34593
O2	0.225694	1.42213	0.96469

(2)

Crystal data

Triclinic, P1	α = 61.3°
a = 14.6 Å	β = 72.2°
b = 11.2 Å	γ = 92.6°
c = 10.4 Å	V = 1373.44 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.903487	0.395167	0.939332
C2	0.853102	0.389627	1.08047
C3	0.885882	0.327222	1.2047
C4	0.969361	0.269747	1.19232
C5	1.01835	0.275767	1.0495
C6	0.985695	0.337628	0.924206
C7	0.991066	0.204471	1.34224
C8	1.12642	0.156527	1.44665
C9	1.227	0.158689	1.40564
C10	1.26856	0.111084	1.52513
C11	1.20691	0.064164	1.6846
C12	1.10556	0.066409	1.71971
C13	1.06566	0.111152	1.60553
C14	1.37026	0.108943	1.49068
C15	1.40814	0.062501	1.60799
C16	1.34688	0.016116	1.76566
C17	1.24825	0.017149	1.8027
C18	1.29296	0.209542	1.23927
C19	1.3217	0.117629	1.18907
C20	1.38604	0.168381	1.0306
C21	1.42151	0.309015	0.92451
C22	1.39528	0.40766	0.969552
C23	1.33054	0.357356	1.12836
C24	1.43183	0.553757	0.861799
C25	1.40615	0.647656	0.908343
C26	1.34271	0.598411	1.06565
C27	1.30579	0.457149	1.17281
C28	1.34422	−0.122208	1.29589
C29	1.2943	−0.275364	1.39998
C30	1.21181	−0.340686	1.39634
C31	1.17559	−0.485494	1.49078
C32	1.22167	−0.566704	1.59074
C33	1.3046	−0.503876	1.59492
C34	1.34085	−0.359828	1.4988
Cl1	1.12044	0.202634	1.01953
Cl2	1.15187	−0.244726	1.27128
N1	1.08747	0.204897	1.32698
N2	1.28656	−0.028317	1.29165
H1	1.19289	−0.679488	1.66459
H2	1.11191	−0.533176	1.48442
H3	1.34126	−0.567165	1.67194
H4	1.40678	−0.308858	1.49703
H5	1.05842	0.031527	1.84092
H6	0.988033	0.111599	1.63343
H7	1.37795	−0.020139	1.85706
H8	1.48617	0.061581	1.57896
H9	1.20013	−0.018183	1.92359
H10	1.41811	0.144084	1.36996
H11	1.40699	0.093327	0.995908
H12	1.47038	0.34657	0.803417
H13	1.25758	0.420175	1.29392
H14	1.32302	0.672826	1.10252
H15	1.48098	0.59017	0.741135
H16	1.43471	0.759558	0.824717
H17	1.21695	−0.064666	1.37346
H18	1.13804	0.243005	1.21656
H19	0.847028	0.318915	1.31708
H20	0.788411	0.4336	1.09371
H21	1.025	0.339241	0.815925
H22	0.878721	0.443357	0.840889
O1	0.922152	0.159193	1.46867
O2	1.43364	−0.087049	1.22327

(3)

Crystal data

Triclinic, P1	α = 63.9°
a = 10.7 Å	β = 61.4°
b = 15.5 Å	γ = 90.2°
c = 11.0 Å	V = 1379.11 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.542239	0.882817	0.672307
C2	0.414369	0.843493	0.688169
C3	0.297738	0.886619	0.723278
C4	0.304015	0.970289	0.741702
C5	0.433309	1.00748	0.727457
C6	0.551019	0.964298	0.692888
C7	0.162929	1.00347	0.780093
C8	0.054627	1.14498	0.782041
C9	0.093551	1.24688	0.727518
C10	−0.016707	1.30013	0.74335
C11	−0.166372	1.24821	0.816478
C12	−0.200454	1.14489	0.870419
C13	−0.094304	1.09388	0.854031
C14	0.017491	1.40413	0.687294
C15	−0.091087	1.45346	0.703918
C16	−0.23927	1.40176	0.777361
C17	−0.275652	1.30128	0.832158
C18	0.250713	1.29948	0.651802
C19	0.298704	1.30724	0.7451
C20	0.448293	1.35742	0.673185
C21	0.546466	1.39716	0.512168
C22	0.503649	1.38965	0.412916
C23	0.353445	1.34024	0.483903
C24	0.605002	1.42955	0.246597
C25	0.560415	1.42128	0.153018
C26	0.411723	1.37262	0.222846
C27	0.310673	1.33325	0.38389
C28	0.226407	1.25352	1.02374
C29	0.097439	1.23061	1.18454
C30	−0.011377	1.28205	1.21242
C31	−0.118474	1.25898	1.36772
C32	−0.117966	1.18405	1.49734
C33	−0.009293	1.13297	1.47217
C34	0.097891	1.15738	1.31711
Cl1	0.457402	1.10706	0.756036
Cl2	−0.017820	1.37812	1.05599
N1	0.167797	1.09669	0.761952
N2	0.196806	1.26606	0.909822
H1	−0.202138	1.1663	1.618
H2	−0.20085	1.30056	1.38526
H3	−0.007463	1.07502	1.57293
H4	0.186187	1.12067	1.29401
H5	−0.314362	1.10523	0.926049
H6	−0.120927	1.01521	0.893818
H7	−0.323925	1.44177	0.789881
H8	−0.062701	1.5331	0.659857
H9	−0.389239	1.26073	0.888398
H10	0.131298	1.44433	0.630315
H11	0.483207	1.36195	0.7482
H12	0.660614	1.43526	0.458588
H13	0.196384	1.29618	0.436709
H14	0.376809	1.36638	0.148359
H15	0.719139	1.46692	0.19439
H16	0.639	1.45211	0.025502
H17	0.088903	1.24923	0.945576
H18	0.266373	1.1394	0.72074
H19	0.196057	0.856987	0.738143
H20	0.405387	0.779273	0.673705
H21	0.648806	0.995209	0.683306
H22	0.634915	0.850076	0.645058
O1	0.051990	0.947015	0.821837
O2	0.349979	1.25786	1.00298

(4)

Crystal data

Triclinic, P1	α = 121.4°
a = 10.9 Å	β = 117.8°
b = 15.4 Å	γ = 113.9°
c = 21.3 Å	V = 1371.72 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.560668	0.857346	0.629189
C2	0.548773	0.744037	0.586007
C3	0.470657	0.640593	0.475433
C4	0.397888	0.644965	0.404392
C5	0.408315	0.758009	0.448114
C6	0.49171	0.865211	0.560879
C7	0.286726	0.511843	0.274842
C8	0.374967	0.398294	0.204876
C9	0.57568	0.458551	0.254095
C10	0.499482	0.315891	0.154106
C11	0.217703	0.112906	0.004579
C12	0.020956	0.058913	−0.040181
C13	0.094298	0.195765	0.055647
C14	0.696042	0.369558	0.198549
C15	0.616762	0.229189	0.099881
C16	0.337847	0.028400	−0.047972
C17	0.142821	−0.027980	−0.094292
C18	0.869528	0.671042	0.411461
C19	0.994085	0.812246	0.449656
C20	1.27325	1.01542	0.598723
C21	1.42163	1.07377	0.70592
C22	1.30473	0.936763	0.672985
C23	1.02438	0.732207	0.523355
C24	1.457	0.996794	0.783743
C25	1.3385	0.861071	0.749069
C26	1.06113	0.658598	0.601138
C27	0.90776	0.595466	0.49104
C28	0.901657	0.855984	0.347491
C29	0.690513	0.738186	0.202309
C30	0.407413	0.56934	0.077745
C31	0.240638	0.478587	−0.048329
C32	0.35418	0.55538	−0.051930
C33	0.635689	0.725739	0.071817
C34	0.800007	0.815866	0.197131
Cl1	0.327459	0.773789	0.367139
Cl2	0.249176	0.471264	0.076191
N1	0.452792	0.537447	0.306073
N2	0.835294	0.745917	0.336438
H1	0.222278	0.483099	−0.15092
H2	0.022476	0.349142	−0.142154
H3	0.726854	0.788637	0.070940
H4	1.02026	0.950753	0.295939
H5	−0.193972	−0.095677	−0.154105
H6	−0.058162	0.153199	0.019242
H7	0.278317	−0.080858	−0.124665
H8	0.770389	0.273216	0.136047
H9	−0.072767	−0.182135	−0.207937
H10	0.910954	0.523744	0.312145
H11	1.36298	1.12107	0.624742
H12	1.63516	1.22967	0.819812
H13	0.694924	0.439363	0.377333
H14	0.968346	0.551595	0.574107
H15	1.67037	1.15312	0.897212
H16	1.45722	0.908711	0.83488
H17	0.641914	0.596833	0.234118
H18	0.652372	0.668751	0.414659
H19	0.461827	0.552347	0.441296
H20	0.60197	0.737293	0.638877
H21	0.501977	0.954129	0.594295
H22	0.623567	0.940268	0.716314
O1	0.059281	0.38358	0.151309
O2	1.1226	1.03777	0.464244

(5)

Crystal data

Triclinic, P1	α = 63.3°
a = 11.1 Å	β = 69.7°
b = 10.7 Å	γ = 119.2°
c = 21.4 Å	V = 1369.07 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.413409	0.014132	0.416022
C2	0.609839	0.209945	0.35369
C3	0.646136	0.308993	0.380592
C4	0.49005	0.216447	0.469912
C5	0.293359	0.021309	0.530546
C6	0.255441	−0.078919	0.503828
C7	0.561755	0.35102	0.484581
C8	0.491575	0.328601	0.615141
C9	0.34907	0.187528	0.719018
C10	0.384296	0.269065	0.755766
C11	0.565473	0.494068	0.685784
C12	0.70697	0.629785	0.581289
C13	0.673471	0.551487	0.546091
C14	0.244013	0.132798	0.860764
C15	0.281047	0.21587	0.89398
C16	0.459868	0.438837	0.824446
C17	0.598965	0.574461	0.722517
C18	0.161155	−0.048218	0.792409
C19	−0.015107	−0.127243	0.825206
C20	−0.193464	−0.353202	0.896228
C21	−0.193416	−0.49537	0.932365
C22	−0.01786	−0.423464	0.900847
C23	0.160822	−0.197546	0.830536
C24	−0.015405	−0.568706	0.937159
C25	0.156849	−0.49493	0.905662
C26	0.333956	−0.271585	0.836351
C27	0.33611	−0.126699	0.799838
C28	−0.161802	−0.023869	0.795342
C29	−0.176668	0.11155	0.790307
C30	−0.179655	0.224526	0.725571
C31	−0.220003	0.323673	0.733323
C32	−0.262777	0.306273	0.807897
C33	−0.263689	0.191699	0.87409
C34	−0.220788	0.09537	0.86498
Cl1	0.083966	−0.103376	0.639551
Cl2	−0.125223	0.251313	0.631076
N1	0.452764	0.242309	0.582055
N2	−0.019063	0.015400	0.790322
H1	−0.295425	0.382898	0.813939
H2	−0.217999	0.413359	0.680986
H3	−0.297983	0.176897	0.93268
H4	−0.221405	0.005121	0.91636
H5	0.846029	0.800859	0.527785
H6	0.781539	0.656391	0.466078
H7	0.487094	0.502161	0.851828
H8	0.171975	0.108739	0.974646
H9	0.737648	0.746324	0.668177
H10	0.106871	−0.039239	0.914795
H11	−0.327832	−0.409875	0.919523
H12	−0.330754	−0.667518	0.986389
H13	0.472934	0.044720	0.746781
H14	0.469939	−0.213639	0.811733
H15	−0.15314	−0.740352	0.990644
H16	0.157258	−0.607653	0.933942
H17	0.096103	0.162716	0.757004
H18	0.32338	0.079463	0.63846
H19	0.797303	0.463373	0.332642
H20	0.734229	0.285202	0.284327
H21	0.101188	−0.228974	0.552184
H22	0.382097	−0.065687	0.396088
O1	0.716126	0.548619	0.40946
O2	−0.281332	−0.168857	0.811517

(6)

Crystal data

Triclinic, P1	α = 101.9°
a = 10.2 Å	β = 85.3°
b = 12.5 Å	γ = 77.4°
c = 11.2 Å	V = 1355.04 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.44666	0.481565	0.841106
C2	0.52922	0.397074	0.747426
C3	0.65	0.412996	0.698022
C4	0.69269	0.512339	0.738372
C5	0.608231	0.595613	0.83386
C6	0.486706	0.580244	0.884604
C7	0.8292	0.511311	0.675466
C8	0.990675	0.630804	0.655394
C9	1.00428	0.739861	0.656815
C10	1.13527	0.761412	0.645675
C11	1.25141	0.670437	0.631687
C12	1.23252	0.561104	0.630524
C13	1.10672	0.54048	0.642189
C14	1.15439	0.871213	0.648495
C15	1.28192	0.889327	0.637309
C16	1.39677	0.799051	0.622741
C17	1.38138	0.691952	0.620066
C18	0.879815	0.832791	0.674593
C19	0.812012	0.848499	0.574218
C20	0.690768	0.933958	0.589646
C21	0.639741	1.00258	0.703063
C22	0.704044	0.990053	0.80795
C23	0.824982	0.9038	0.793203
C24	0.651129	1.05936	0.92624
C25	0.714755	1.04468	1.02688
C26	0.834661	0.959453	1.01269
C27	0.88857	0.890957	0.899008
C28	0.814187	0.783202	0.34862
C29	0.914606	0.740749	0.233637
C30	1.04163	0.764279	0.216838
C31	1.12319	0.724667	0.103528
C32	1.07921	0.660662	0.005308
C33	0.952656	0.637466	0.019392
C34	0.871715	0.678309	0.132056
Cl1	0.649352	0.721214	0.900151
Cl2	1.10377	0.846768	0.333378
N1	0.861067	0.612184	0.674509
N2	0.864253	0.778364	0.457727
H1	1.14378	0.629799	−0.082435
H2	1.22048	0.74515	0.093367
H3	0.917025	0.588321	−0.057216
H4	0.771528	0.663426	0.144755
H5	1.32101	0.49182	0.620343
H6	1.09382	0.456455	0.639982
H7	1.49693	0.814682	0.613954
H8	1.29459	0.973999	0.639876
H9	1.469	0.621773	0.609193
H10	1.0664	0.940953	0.659887
H11	0.639028	0.94222	0.510504
H12	0.547056	1.06774	0.713573
H13	0.980823	0.825621	0.888792
H14	0.884861	0.947982	1.09242
H15	0.558649	1.12457	0.935749
H16	0.673282	1.09828	1.11724
H17	0.961659	0.735782	0.451252
H18	0.786025	0.683258	0.702402
H19	0.717187	0.34793	0.626148
H20	0.499687	0.319091	0.713094
H21	0.424831	0.646327	0.958861
H22	0.351595	0.470784	0.881223
O1	0.907291	0.419621	0.630714
O2	0.694942	0.817043	0.340176

(7)

Crystal data

Triclinic, P1	α = 70.6°
a = 11.3 Å	β = 89.3°
b = 10.6 Å	γ = 58.8°
c = 14.6 Å	V = 1378.98 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.9454	0.557589	0.200568
C2	1.05347	0.472773	0.156561
C3	1.19342	0.388328	0.205005
C4	1.22855	0.385902	0.2975
C5	1.11797	0.473005	0.340263
C6	0.977544	0.55836	0.291901
C7	1.3809	0.28625	0.348715
C8	1.62219	0.189515	0.321255
C9	1.70803	0.247222	0.293076
C10	1.85845	0.141042	0.328595
C11	1.9171	−0.020983	0.392681
C12	1.82445	−0.073721	0.419186
C13	1.68156	0.027731	0.384784
C14	1.95236	0.192575	0.302871
C15	2.09588	0.089133	0.338427
C16	2.15341	−0.071175	0.401371
C17	2.06531	−0.124647	0.427873
C18	1.6514	0.4147	0.224595
C19	1.65406	0.45303	0.123865
C20	1.60737	0.611832	0.060964
C21	1.56161	0.727552	0.099017
C22	1.55936	0.694174	0.200865
C23	1.60582	0.535312	0.26438
C24	1.51318	0.812921	0.240998
C25	1.51236	0.776989	0.340281
C26	1.55796	0.619921	0.403433
C27	1.60347	0.502132	0.366679
C28	1.70325	0.346451	−0.009641
C29	1.77029	0.196038	−0.030924
C30	1.78282	0.051232	0.021795
C31	1.844	−0.073372	−0.011784
C32	1.89441	−0.055872	−0.099345
C33	1.88194	0.087250	−0.153946
C34	1.81965	0.210749	−0.120151
Cl1	1.14957	0.484483	0.452205
Cl2	1.72024	0.016954	0.131743
N1	1.47455	0.287407	0.287129
N2	1.7064	0.330975	0.087067
H1	1.94238	−0.1538	−0.124821
H2	1.85084	−0.183055	0.031197
H3	1.91995	0.102914	−0.222925
H4	1.80592	0.324607	−0.162349
H5	1.86867	−0.197323	0.467503
H6	1.6114	−0.013271	0.406001
H7	2.26702	−0.151642	0.428846
H8	2.16565	0.13145	0.317977
H9	2.10806	−0.247777	0.47656
H10	1.90924	0.31591	0.25496
H11	1.6088	0.638462	−0.016974
H12	1.52645	0.848324	0.049950
H13	1.63773	0.3819	0.415826
H14	1.55675	0.591938	0.481911
H15	1.47825	0.933363	0.191401
H16	1.47663	0.868867	0.370426
H17	1.74667	0.220404	0.13919
H18	1.43712	0.382567	0.222571
H19	1.27847	0.319385	0.17205
H20	1.02918	0.471486	0.085311
H21	0.894208	0.625549	0.326401
H22	0.835373	0.624196	0.163837
O1	1.41865	0.205216	0.436997
O2	1.65404	0.473806	−0.079653

(8)

Crystal data

Triclinic, P1	α = 95.0°
a = 10.9 Å	β = 66.8°
b = 13.4 Å	γ = 74.0°
c = 11.2 Å	V = 1404.04 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.734515	0.449015	0.400213
C2	0.68182	0.370104	0.449219
C3	0.596415	0.386183	0.58456
C4	0.560059	0.480596	0.674462
C5	0.615518	0.558344	0.622909
C6	0.702109	0.542751	0.487131
C7	0.468467	0.481434	0.817559
C8	0.282092	0.597847	1.03489
C9	0.217743	0.702991	1.1063
C10	0.125224	0.726597	1.24596
C11	0.099687	0.642201	1.31033
C12	0.165621	0.537071	1.23302
C13	0.253643	0.514625	1.0994
C14	0.056347	0.831954	1.3243
C15	−0.031117	0.851811	1.45841
C16	−0.055426	0.768001	1.52176
C17	0.008766	0.665339	1.44866
C18	0.239236	0.792002	1.03896
C19	0.315844	0.852005	1.0628
C20	0.330882	0.938895	1.00148
C21	0.268527	0.965803	0.918466
C22	0.186796	0.908551	0.892421
C23	0.170924	0.821232	0.953992
C24	0.119593	0.936727	0.808479
C25	0.038158	0.881833	0.786451
C26	0.020301	0.796503	0.848687
C27	0.084850	0.766897	0.930181
C28	0.384687	0.900627	1.23649
C29	0.475453	0.863936	1.30738
C30	0.62101	0.8056	1.24578
C31	0.698234	0.783949	1.32042
C32	0.630186	0.820901	1.45814
C33	0.485752	0.880729	1.52124
C34	0.410333	0.903015	1.44577
Cl1	0.585585	0.677361	0.724067
Cl2	0.713251	0.758867	1.07305
N1	0.371385	0.576745	0.897606
N2	0.385018	0.826092	1.14492
H1	0.6908	0.803479	1.51588
H2	0.811154	0.738869	1.26966
H3	0.432594	0.910666	1.62868
H4	0.298647	0.951764	1.49216
H5	0.145184	0.472702	1.28148
H6	0.304689	0.433973	1.04131
H7	−0.125	0.785002	1.62783
H8	−0.082400	0.933111	1.51617
H9	−0.009231	0.599865	1.49575
H10	0.073711	0.897476	1.27743
H11	0.391961	0.983618	1.02237
H12	0.28124	1.0321	0.871319
H13	0.069105	0.701767	0.978532
H14	−0.045542	0.753946	0.832475
H15	0.133356	1.00326	0.762118
H16	−0.013139	0.90423	0.722017
H17	0.427562	0.748686	1.14303
H18	0.37502	0.641897	0.859117
H19	0.556148	0.325295	0.625899
H20	0.707424	0.296246	0.382192
H21	0.744075	0.604388	0.451047
H22	0.801849	0.437703	0.294515
O1	0.481235	0.397108	0.853104
O2	0.313378	0.994374	1.26326

(9)

Crystal data

Triclinic, P1	α = 65.5°
a = 12.0 Å	β = 81.4°
b = 11.9 Å	γ = 77.2°
c = 10.9 Å	V = 1378.76 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.619179	0.796546	0.611891
C2	0.692739	0.866436	0.512543
C3	0.657186	0.936263	0.383285
C4	0.547732	0.940816	0.349234
C5	0.475916	0.868025	0.450612
C6	0.511328	0.796744	0.580615
C7	0.527654	1.02183	0.202506
C8	0.382516	1.13934	0.033359
C9	0.267606	1.16092	0.009387
C10	0.231104	1.23409	−0.123969
C11	0.312241	1.28651	−0.231247
C12	0.427516	1.26499	−0.201307
C13	0.46247	1.19452	−0.073840
C14	0.115152	1.25692	−0.154052
C15	0.082270	1.32695	−0.283133
C16	0.162993	1.37829	−0.389063
C17	0.275655	1.35833	−0.363119
C18	0.179858	1.11061	0.119804
C19	0.150456	0.99349	0.157633
C20	0.062053	0.95471	0.260283
C21	0.006967	1.03048	0.32479
C22	0.034615	1.15016	0.291186
C23	0.121262	1.19091	0.186731
C24	−0.021780	1.22966	0.357131
C25	0.005763	1.34606	0.321609
C26	0.091236	1.38714	0.218054
C27	0.147428	1.31186	0.152267
C28	0.214131	0.785161	0.147655
C29	0.256574	0.719697	0.053800
C30	0.323625	0.598528	0.097632
C31	0.353493	0.535123	0.011802
C32	0.315835	0.590034	−0.117754
C33	0.248666	0.709397	−0.16276
C34	0.219777	0.772579	−0.077109
Cl1	0.34109	0.85509	0.422139
Cl2	0.378745	0.524383	0.255047
N1	0.417698	1.06753	0.16453
N2	0.201723	0.914557	0.090646
H1	0.339327	0.539002	−0.183127
H2	0.406699	0.44246	0.047738
H3	0.218223	0.752888	−0.263432
H4	0.16507	0.864677	−0.110727
H5	0.489743	1.30597	−0.282091
H6	0.55085	1.17819	−0.052499
H7	0.135705	1.43358	−0.490552
H8	−0.006905	1.34332	−0.303828
H9	0.338797	1.39749	−0.443587
H10	0.052238	1.21853	−0.073192
H11	0.040101	0.86336	0.287638
H12	−0.060073	0.998941	0.403019
H13	0.212824	1.34479	0.072549
H14	0.112867	1.47931	0.189836
H15	−0.087564	1.1966	0.436614
H16	−0.037990	1.40651	0.372725
H17	0.24626	0.954488	0.002244
H18	0.353899	1.03961	0.235966
H19	0.713104	0.990149	0.30328
H20	0.777714	0.865964	0.535548
H21	0.453689	0.740965	0.656041
H22	0.645657	0.740874	0.713661
O1	0.611713	1.0458	0.124264
O2	0.188449	0.725994	0.265939

(10)

Crystal data

Triclinic, P1	α = 65.0°
a = 13.8 Å	β = 109.4°
b = 10.9 Å	γ = 111.7°
c = 11.5 Å	V = 1418.23 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.975598	0.103404	0.767893
C2	0.892232	0.007560	0.829848
C3	0.90121	−0.126067	0.911098
C4	0.993252	−0.167178	0.935218
C5	1.07523	−0.069851	0.869855
C6	1.06651	0.064402	0.787161
C7	0.985438	−0.317966	1.02358
C8	1.09559	−0.474219	1.19842
C9	1.20101	−0.47578	1.26333
C10	1.22325	−0.602068	1.36163
C11	1.13751	−0.72606	1.39173
C12	1.03199	−0.718625	1.32488
C13	1.01059	−0.596906	1.23176
C14	1.32873	−0.609069	1.43216
C15	1.34786	−0.732546	1.52541
C16	1.26295	−0.855425	1.55365
C17	1.16	−0.851651	1.4882
C18	1.28917	−0.343541	1.23678
C19	1.35063	−0.309522	1.14708
C20	1.4345	−0.183286	1.12402
C21	1.45423	−0.093400	1.18858
C22	1.39301	−0.122478	1.27962
C23	1.30959	−0.249853	1.3047
C24	1.41261	−0.029448	1.34613
C25	1.35257	−0.060486	1.4347
C26	1.27035	−0.186728	1.46028
C27	1.24938	−0.279206	1.39727
C28	1.3599	−0.370834	0.967613
C29	1.35185	−0.491247	0.929829
C30	1.36183	−0.626025	1.01279
C31	1.3571	−0.723714	0.961478
C32	1.34227	−0.68888	0.826591
C33	1.33333	−0.555348	0.742364
C34	1.33903	−0.458591	0.794345
Cl1	1.1899	−0.110529	0.881094
Cl2	1.38339	−0.681185	1.18395
N1	1.07858	−0.346812	1.10469
N2	1.33005	−0.402581	1.08179
H1	1.33839	−0.766139	0.787899
H2	1.36572	−0.826625	1.0286
H3	1.32244	−0.52663	0.636797
H4	1.3343	−0.352891	0.731508
H5	0.966284	−0.812266	1.34883
H6	0.929733	−0.591852	1.18072
H7	1.27935	−0.952286	1.62749
H8	1.42913	−0.735596	1.57827
H9	1.09381	−0.945259	1.50963
H10	1.39444	−0.514946	1.41146
H11	1.48074	−0.158356	1.05301
H12	1.51838	0.003070	1.16985
H13	1.18629	−0.376347	1.41807
H14	1.22327	−0.211238	1.53078
H15	1.47641	0.067246	1.32571
H16	1.36823	0.011538	1.48531
H17	1.28988	−0.502695	1.12472
H18	1.14634	−0.267428	1.09332
H19	0.836594	−0.203996	0.958264
H20	0.820304	0.036567	0.814143
H21	1.1312	0.136794	0.737462
H22	0.969838	0.208388	0.703398
O1	0.898044	−0.404108	1.02406
O2	1.39047	−0.250529	0.894765

(11)

Crystal data

Triclinic, P1	α = 66.7°
a = 13.7 Å	β = 75.2°
b = 10.5 Å	γ = 100.5°
c = 11.0 Å	V = 1337.37 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.436964	0.765689	0.468631
C2	0.332536	0.766916	0.491182
C3	0.312819	0.898301	0.432358
C4	0.395311	1.03156	0.350581
C5	0.499727	1.0271	0.327895
C6	0.520701	0.895814	0.385771
C7	0.360287	1.16423	0.296407
C8	0.391679	1.41832	0.254736
C9	0.297841	1.42973	0.327283
C10	0.280719	1.56881	0.277989
C11	0.362073	1.69352	0.159501
C12	0.458038	1.67678	0.091701
C13	0.472168	1.5426	0.137628
C14	0.185189	1.5877	0.344728
C15	0.171173	1.7225	0.29632
C16	0.251822	1.84558	0.179362
C17	0.345285	1.83107	0.112524
C18	0.216201	1.30402	0.458973
C19	0.122924	1.22785	0.458247
C20	0.041587	1.11824	0.586392
C21	0.054907	1.08481	0.713065
C22	0.149443	1.15868	0.719209
C23	0.231109	1.27083	0.590647
C24	0.164105	1.12519	0.849689
C25	0.255246	1.19964	0.854299
C26	0.335549	1.31174	0.727626
C27	0.323843	1.34645	0.599298
C28	0.021989	1.28126	0.301222
C29	0.019094	1.3054	0.15792
C30	0.104068	1.38107	0.026942
C31	0.088496	1.39608	−0.097586
C32	−0.011924	1.33598	−0.093649
C33	−0.097771	1.26259	0.034820
C34	−0.081695	1.24934	0.157844
Cl1	0.610804	1.18427	0.22139
Cl2	0.232267	1.4673	0.007821
N1	0.413756	1.28395	0.299684
N2	0.110645	1.25848	0.327393
H1	−0.022867	1.34798	−0.191334
H2	0.155823	1.45617	−0.197193
H3	−0.176917	1.21659	0.039024
H4	−0.147473	1.19538	0.259101
H5	0.520076	1.77178	0.001716
H6	0.544735	1.52858	0.084138
H7	0.239596	1.95147	0.142298
H8	0.097055	1.73425	0.348371
H9	0.407941	1.92498	0.022074
H10	0.122235	1.49366	0.433981
H11	−0.031119	1.06315	0.581553
H12	−0.007546	1.00044	0.811264
H13	0.385798	1.43367	0.502646
H14	0.407156	1.37139	0.731711
H15	0.101281	1.03927	0.946627
H16	0.26552	1.17309	0.955051
H17	0.173235	1.2599	0.253114
H18	0.480771	1.28258	0.321775
H19	0.232079	0.901781	0.447493
H20	0.266523	0.665785	0.554783
H21	0.602709	0.896884	0.364717
H22	0.453822	0.663751	0.513968
O1	0.284692	1.15798	0.256694
O2	−0.055039	1.27881	0.38904

(12)

Crystal data

Monoclinic, P21/a	c = 11.1 Å
a = 18.9 Å	β = 87.2°
b = 13.2 Å	V = 2758.9 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.985048	0.050545	0.685457
C2	0.921226	0.073451	0.633724
C3	0.921523	0.13359	0.531244
C4	0.984711	0.170724	0.47603
C5	1.04816	0.147809	0.530626
C6	1.04833	0.088396	0.634547
C7	0.974834	0.235434	0.366153
C8	1.02246	0.269202	0.15618
C9	1.07696	0.245993	0.070746
C10	1.07706	0.290863	−0.046759
C11	1.02079	0.357044	−0.076395
C12	0.966668	0.377768	0.013111
C13	0.966992	0.33613	0.126147
C14	1.13221	0.272579	−0.136019
C15	1.13094	0.316565	−0.248257
C16	1.07479	0.381219	−0.277574
C17	1.02095	0.400987	−0.192947
C18	1.13751	0.180481	0.103119
C19	1.18986	0.218781	0.175233
C20	1.24826	0.157656	0.205794
C21	1.25372	0.060520	0.163818
C22	1.20231	0.018120	0.090076
C23	1.14335	0.078918	0.059656
C24	1.20771	−0.082402	0.046544
C25	1.15687	−0.122149	−0.024180
C26	1.09819	−0.062436	−0.053806
C27	1.09146	0.035374	−0.012966
C28	1.22615	0.37257	0.287799
C29	1.21006	0.483785	0.293587
C30	1.21471	0.539964	0.400394
C31	1.20288	0.643944	0.400808
C32	1.18716	0.693668	0.294888
C33	1.18276	0.639539	0.187907
C34	1.19408	0.535764	0.188121
Cl1	1.12971	0.195771	0.476962
Cl2	1.23154	0.483884	0.537454
N1	1.02313	0.224049	0.270654
N2	1.18465	0.320088	0.210826
H1	1.1784	0.774844	0.296501
H2	1.20595	0.685154	0.485054
H3	1.17096	0.677743	0.104548
H4	1.1924	0.493984	0.103827
H5	0.923865	0.428596	−0.008786
H6	0.925614	0.352707	0.194189
H7	1.07445	0.415241	−0.366771
H8	1.17364	0.301383	−0.315203
H9	0.977492	0.450977	−0.213985
H10	1.1756	0.222899	−0.114562
H11	1.28751	0.189606	0.262563
H12	1.29864	0.014349	0.187512
H13	1.04611	0.080695	−0.036065
H14	1.05788	−0.094227	−0.109345
H15	1.25305	−0.127622	0.070492
H16	1.16152	−0.199335	−0.057165
H17	1.1428	0.357486	0.178672
H18	1.06336	0.174759	0.281696
H19	0.872344	0.154259	0.490811
H20	0.871377	0.045117	0.673545
H21	1.0984	0.073152	0.675054
H22	0.98578	0.004002	0.766149
O1	0.923594	0.29201	0.366091
O2	1.27286	0.334407	0.344853

(13)

Crystal data

Triclinic, P1	α = 67.6°
a = 10.9 Å	β = 62.7°
b = 14.9 Å	γ = 88.5°
c = 10.5 Å	V = 1382.34 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.397164	0.399895	0.756931
C2	0.382259	0.344115	0.683258
C3	0.318099	0.377298	0.590732
C4	0.268562	0.466659	0.566994
C5	0.283959	0.521027	0.643398
C6	0.347261	0.488006	0.737708
C7	0.200979	0.488869	0.463527
C8	0.157372	0.623092	0.268341
C9	0.160202	0.724022	0.204658
C10	0.110994	0.764649	0.093568
C11	0.062193	0.701545	0.046658
C12	0.063870	0.599751	0.112563
C13	0.109988	0.560722	0.219884
C14	0.10876	0.86668	0.027408
C15	0.060506	0.903619	−0.078862
C16	0.012464	0.840991	−0.125184
C17	0.013502	0.741971	−0.063431
C18	0.210834	0.790626	0.252883
C19	0.12059	0.821019	0.366712
C20	0.17416	0.885489	0.407374
C21	0.315215	0.920375	0.333042
C22	0.411992	0.893345	0.213723
C23	0.359109	0.828045	0.173341
C24	0.558405	0.929356	0.134298
C25	0.650356	0.902418	0.018435
C26	0.598608	0.838162	−0.02251
C27	0.456963	0.801805	0.052910
C28	−0.122511	0.84717	0.4854
C29	−0.273009	0.795483	0.585709
C30	−0.382203	0.839156	0.565157
C31	−0.52177	0.791891	0.667525
C32	−0.554532	0.701397	0.792837
C33	−0.447847	0.657241	0.815825
C34	−0.308689	0.704304	0.712544
Cl1	0.221476	0.631392	0.631237
Cl2	−0.349791	0.950182	0.409004
N1	0.209055	0.585377	0.374991
N2	−0.025573	0.786945	0.449745
H1	−0.663913	0.665645	0.872279
H2	−0.604038	0.826676	0.647759
H3	−0.472616	0.586849	0.913816
H4	−0.2248	0.671206	0.731186
H5	0.027424	0.551497	0.076499
H6	0.109915	0.482802	0.270484
H7	−0.025296	0.871334	−0.209383
H8	0.059154	0.981886	−0.127593
H9	−0.023290	0.692839	−0.097930
H10	0.14519	0.915513	0.062391
H11	0.100684	0.907322	0.497362
H12	0.354512	0.969514	0.365607
H13	0.418194	0.752777	0.019940
H14	0.671385	0.817314	−0.114742
H15	0.59662	0.979052	0.166874
H16	0.762544	0.930535	−0.041940
H17	−0.059437	0.722939	0.45403
H18	0.251258	0.636793	0.391538
H19	0.302675	0.334465	0.53436
H20	0.420171	0.274844	0.698211
H21	0.35619	0.531818	0.79587
H22	0.446766	0.37491	0.83026
O1	0.147987	0.419622	0.459028
O2	−0.089474	0.934738	0.444623

(14)

Crystal data

Monoclinic, P21/n	c = 17.8 Å
a = 10.9 Å	β = 80.5°
b = 14.6 Å	V = 2791.91 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.495685	0.075927	0.736043
C2	0.45037	0.160576	0.76321
C3	0.322999	0.176949	0.774322
C4	0.239054	0.11024	0.758149
C5	0.286559	0.025300	0.730995
C6	0.413974	0.008256	0.720357
C7	0.103672	0.134245	0.765718
C8	−0.056468	0.229633	0.843666
C9	−0.111682	0.251146	0.917684
C10	−0.226108	0.301087	0.930379
C11	−0.282739	0.327572	0.866851
C12	−0.222192	0.304672	0.792423
C13	−0.112366	0.257467	0.780431
C14	−0.286403	0.32513	1.00478
C15	−0.397047	0.372247	1.01537
C16	−0.45309	0.398026	0.952403
C17	−0.396657	0.37607	0.87966
C18	−0.051672	0.224387	0.984056
C19	−0.082593	0.142345	1.02246
C20	−0.026647	0.118105	1.08647
C21	0.058919	0.174961	1.1104
C22	0.094262	0.258468	1.073
C23	0.037524	0.283676	1.00913
C24	0.183541	0.317184	1.09703
C25	0.216149	0.397934	1.05975
C26	0.159893	0.423297	0.996708
C27	0.072827	0.367875	0.972035
C28	−0.204962	−0.001015	1.01893
C29	−0.305072	−0.043933	0.9811
C30	−0.325046	−0.035929	0.905389
C31	−0.423516	−0.081004	0.880347
C32	−0.504072	−0.134919	0.930497
C33	−0.485005	−0.145208	1.00564
C34	−0.386207	−0.100687	1.02982
Cl1	0.189657	−0.062924	0.712574
Cl2	−0.225295	0.025520	0.836646
N1	0.057637	0.18322	0.830472
N2	−0.168698	0.085256	0.99538
H1	−0.580749	−0.169444	0.910398
H2	−0.435194	−0.073813	0.821142
H3	−0.546541	−0.188018	1.04514
H4	−0.368028	−0.108704	1.08772
H5	−0.264512	0.325453	0.743815
H6	−0.068206	0.239532	0.723309
H7	−0.540533	0.435254	0.961662
H8	−0.441782	0.389942	1.07281
H9	−0.43867	0.395651	0.830611
H10	−0.243734	0.305759	1.05352
H11	−0.052373	0.053913	1.1148
H12	0.101429	0.155574	1.1593
H13	0.029263	0.388187	0.923883
H14	0.185378	0.487494	0.967615
H15	0.225876	0.296946	1.14579
H16	0.284737	0.442475	1.07866
H17	−0.204007	0.110928	0.950526
H18	0.10411	0.178488	0.875126
H19	0.286844	0.243169	0.79483
H20	0.513661	0.213689	0.775531
H21	0.448113	−0.058364	0.699967
H22	0.594952	0.061946	0.727135
O1	0.043280	0.11547	0.715891
O2	−0.166782	−0.041722	1.07051

(15)

Crystal data

Monoclinic, P21/c	c = 19.6 Å
a = 13.8 Å	β = 80.5°
b = 10.5 Å	V = 2798.62 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.941836	0.967159	0.095857
C2	0.922105	1.09107	0.076933
C3	0.8607	1.11157	0.028518
C4	0.817335	1.00957	−0.001281
C5	0.837774	0.885469	0.018732
C6	0.89992	0.864284	0.066683
C7	0.748527	1.03473	−0.051687
C8	0.737948	1.16834	−0.154671
C9	0.771311	1.28504	−0.183228
C10	0.723319	1.34175	−0.234918
C11	0.641523	1.27845	−0.256038
C12	0.610215	1.16039	−0.225018
C13	0.656515	1.10589	−0.175703
C14	0.753326	1.46096	−0.265667
C15	0.705195	1.51373	−0.314784
C16	0.624675	1.45057	−0.335828
C17	0.593655	1.33538	−0.30688
C18	0.854804	1.35182	−0.159072
C19	0.839285	1.41865	−0.097064
C20	0.918014	1.48253	−0.073204
C21	1.01064	1.4775	−0.111007
C22	1.03051	1.40992	−0.174176
C23	0.951448	1.34644	−0.198722
C24	1.12627	1.40345	−0.213305
C25	1.14389	1.3367	−0.274247
C26	1.06591	1.27342	−0.298523
C27	0.972093	1.27813	−0.26186
C28	0.7206	1.42879	0.011753
C29	0.613231	1.41369	0.039788
C30	0.565743	1.48763	0.094819
C31	0.468522	1.46347	0.123881
C32	0.417906	1.36318	0.099390
C33	0.464078	1.28747	0.045509
C34	0.560812	1.31309	0.016118
Cl1	0.790079	0.75315	−0.017493
Cl2	0.623875	1.61624	0.126574
N1	0.787686	1.11409	−0.104899
N2	0.743809	1.42435	−0.058930
H1	0.342325	1.3444	0.122858
H2	0.433255	1.52365	0.16568
H3	0.425758	1.20782	0.026687
H4	0.597081	1.25077	−0.024502
H5	0.547961	1.11214	−0.241096
H6	0.632001	1.01607	−0.151748
H7	0.58744	1.49343	−0.374772
H8	0.729348	1.60501	−0.337702
H9	0.531584	1.28591	−0.322493
H10	0.81524	1.51012	−0.249857
H11	0.903479	1.53343	−0.024683
H12	1.07066	1.52664	−0.09249
H13	0.912477	1.22933	−0.280896
H14	1.08024	1.2205	−0.346697
H15	1.18575	1.45239	−0.194002
H16	1.21764	1.33226	−0.303839
H17	0.688302	1.40697	−0.085473
H18	0.854789	1.15122	−0.10272
H19	0.844455	1.20902	0.015229
H20	0.95362	1.1721	0.099867
H21	0.915195	0.767069	0.080591
H22	0.989886	0.949793	0.133491
O1	0.665957	0.989914	−0.044850
O2	0.78196	1.43777	0.049752

(16)

Crystal data

Monoclinic, P21/c	c = 8.7 Å
a = 19.4 Å	β = 90.9°
b = 15.9 Å	V = 2702.33 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.509335	0.310091	0.526392
C2	0.54013	0.234854	0.484455
C3	0.512932	0.15948	0.534719
C4	0.455148	0.157381	0.628191
C5	0.425147	0.233568	0.669542
C6	0.452066	0.309623	0.619874
C7	0.430326	0.071954	0.675528
C8	0.326664	−0.019803	0.657556
C9	0.260975	−0.026471	0.592562
C10	0.222639	−0.102113	0.610457
C11	0.251163	−0.169234	0.6989
C12	0.317438	−0.158888	0.765262
C13	0.354573	−0.086926	0.745733
C14	0.1566	−0.113468	0.542127
C15	0.12083	−0.186821	0.562018
C16	0.148915	−0.25277	0.650904
C17	0.212898	−0.243963	0.717582
C18	0.231879	0.042822	0.496671
C19	0.180839	0.095694	0.550853
C20	0.153403	0.159877	0.454647
C21	0.176014	0.169331	0.307875
C22	0.227268	0.116511	0.247024
C23	0.25548	0.052144	0.342513
C24	0.250737	0.125764	0.094990
C25	0.300081	0.073248	0.037906
C26	0.32761	0.008878	0.131342
C27	0.305973	−0.001543	0.279516
C28	0.095169	0.108662	0.754237
C29	0.078095	0.093681	0.920437
C30	0.097266	0.026965	1.01633
C31	0.071796	0.019527	1.16431
C32	0.026255	0.078886	1.21958
C33	0.005494	0.145241	1.12601
C34	0.030545	0.151321	0.978423
Cl1	0.353942	0.23653	0.788777
Cl2	0.153462	−0.051287	0.956883
N1	0.363742	0.054256	0.634935
N2	0.159938	0.090095	0.704465
H1	0.006783	0.072735	1.33517
H2	0.087848	−0.033330	1.23446
H3	−0.030597	0.191639	1.16741
H4	0.01347	0.200998	0.901888
H5	0.339306	−0.209753	0.833174
H6	0.405536	−0.079865	0.795299
H7	0.119917	−0.310298	0.665869
H8	0.070348	−0.194154	0.508705
H9	0.235365	−0.294363	0.785729
H10	0.134537	−0.063283	0.473199
H11	0.113991	0.200439	0.499336
H12	0.154598	0.218838	0.235997
H13	0.327094	−0.051781	0.34973
H14	0.36617	−0.033126	0.085484
H15	0.228705	0.175327	0.024127
H16	0.317762	0.080784	−0.078914
H17	0.19091	0.056488	0.775688
H18	0.337929	0.099807	0.577421
H19	0.536711	0.100277	0.504552
H20	0.585035	0.234939	0.411962
H21	0.427992	0.367688	0.655266
H22	0.53009	0.369485	0.487591
O1	0.470132	0.023057	0.737801
O2	0.050828	0.139765	0.671271

(17)

Crystal data

Triclinic, P1	α = 66.2°
a = 16.6 Å	β = 106.3°
b = 8.8 Å	γ = 86.6°
c = 11.0 Å	V = 1380.55 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.878323	0.421935	0.811806
C2	0.959768	0.358211	0.913307
C3	0.969151	0.314288	1.05358
C4	0.898646	0.327956	1.09769
C5	0.817584	0.396006	0.992982
C6	0.807382	0.442433	0.851427
C7	0.918519	0.278145	1.25299
C8	0.860937	0.134968	1.44892
C9	0.792289	0.061622	1.47916
C10	0.786999	0.006380	1.61746
C11	0.850743	0.031618	1.72213
C12	0.918566	0.10844	1.6858
C13	0.92457	0.15858	1.55372
C14	0.719965	−0.073266	1.65514
C15	0.716085	−0.123537	1.78887
C16	0.778787	−0.097192	1.89195
C17	0.844736	−0.021382	1.85894
C18	0.728487	0.031173	1.36907
C19	0.649226	0.139767	1.28803
C20	0.59057	0.109382	1.18182
C21	0.611411	−0.026234	1.15821
C22	0.691273	−0.139406	1.23679
C23	0.750635	−0.110027	1.34349
C24	0.71354	−0.279398	1.21228
C25	0.79149	−0.387569	1.29014
C26	0.85022	−0.359807	1.39658
C27	0.830451	−0.22505	1.42283
C28	0.549697	0.369596	1.27459
C29	0.539268	0.516619	1.31008
C30	0.590254	0.539821	1.42456
C31	0.567552	0.678221	1.44746
C32	0.492967	0.79648	1.35652
C33	0.440361	0.77516	1.24336
C34	0.46318	0.636138	1.22258
Cl1	0.725442	0.435502	1.03133
Cl2	0.68433	0.397777	1.54729
N1	0.864987	0.184756	1.31265
N2	0.630452	0.284573	1.3071
H1	0.475948	0.904105	1.37508
H2	0.608762	0.691055	1.53753
H3	0.381403	0.865785	1.1722
H4	0.42213	0.6143	1.13745
H5	0.967278	0.127161	1.76566
H6	0.976617	0.216757	1.52649
H7	0.774736	−0.137328	1.99715
H8	0.664215	−0.184171	1.81567
H9	0.893634	−0.001024	1.93753
H10	0.671561	−0.093935	1.57638
H11	0.529319	0.194799	1.12101
H12	0.565938	−0.047286	1.07626
H13	0.875858	−0.20573	1.5057
H14	0.911625	−0.446242	1.45874
H15	0.667457	−0.299478	1.13033
H16	0.808018	−0.494589	1.27053
H17	0.680217	0.313927	1.36592
H18	0.817737	0.157344	1.24802
H19	1.03224	0.267545	1.13407
H20	1.0158	0.343924	0.883213
H21	0.743692	0.495741	0.773376
H22	0.869777	0.45771	0.701342
O1	0.979737	0.319287	1.31605
O2	0.484521	0.334078	1.21535

(18)

Crystal data

Monoclinic, P21/c	c = 19.7 Å
a = 10.9 Å	β = 57.0°
b = 15.2 Å	V = 2742.34 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.631511	0.836066	0.050323
C2	0.611775	0.918712	0.084949
C3	0.661728	0.992402	0.035734
C4	0.729762	0.986292	−0.048376
C5	0.748731	0.902381	−0.081759
C6	0.700668	0.82785	−0.032975
C7	0.776077	1.07364	−0.091267
C8	0.792734	1.16457	−0.198869
C9	0.857943	1.16584	−0.282123
C10	0.871711	1.2474	−0.321724
C11	0.819691	1.32617	−0.275263
C12	0.75335	1.32115	−0.190363
C13	0.73929	1.24297	−0.152701
C14	0.937121	1.25279	−0.406614
C15	0.950582	1.33206	−0.443322
C16	0.899251	1.4099	−0.397247
C17	0.835066	1.40675	−0.314888
C18	0.910939	1.08332	−0.330418
C19	1.05402	1.05463	−0.362892
C20	1.10434	0.975861	−0.408871
C21	1.01318	0.928022	−0.422254
C22	0.867902	0.954901	−0.391605
C23	0.816744	1.03381	−0.34534
C24	0.772943	0.906197	−0.405469
C25	0.632357	0.933898	−0.375024
C26	0.581233	1.01201	−0.329263
C27	0.67071	1.06069	−0.314742
C28	1.28749	1.08875	−0.3738
C29	1.36341	1.15851	−0.355418
C30	1.30877	1.20248	−0.281926
C31	1.39567	1.26202	−0.272599
C32	1.53806	1.27839	−0.336571
C33	1.59506	1.23438	−0.409805
C34	1.50862	1.17442	−0.41829
Cl1	0.838472	0.884906	−0.185902
Cl2	1.13268	1.18426	−0.198266
N1	0.772832	1.08406	−0.159143
N2	1.14576	1.10539	−0.349312
H1	1.60465	1.32511	−0.328736
H2	1.35058	1.29463	−0.214744
H3	1.70677	1.24622	−0.45979
H4	1.55171	1.13744	−0.473905
H5	0.712571	1.38102	−0.154808
H6	0.68993	1.23989	−0.087972
H7	0.910546	1.4721	−0.427051
H8	1.00108	1.33485	−0.508427
H9	0.794981	1.46628	−0.278726
H10	0.97651	1.19307	−0.442321
H11	1.21532	0.954988	−0.432484
H12	1.05315	0.867865	−0.457453
H13	0.630611	1.1209	−0.279798
H14	0.470054	1.0339	−0.30541
H15	0.813877	0.846199	−0.440854
H16	0.56042	0.896053	−0.386033
H17	1.09952	1.16073	−0.316768
H18	0.764941	1.02996	−0.186275
H19	0.651033	1.05745	0.060745
H20	0.558608	0.925647	0.149968
H21	0.718791	0.763853	−0.061011
H22	0.59394	0.777599	0.087901
O1	0.808364	1.13303	−0.061945
O2	1.35643	1.02362	−0.411506

(19)

Crystal data

Monoclinic, C2/c	c = 30.1 Å
a = 19.0 Å	β = 60.9°
b = 11.4 Å	V = 5677.08 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.171372	0.237564	0.353457
C2	0.144079	0.284361	0.321875
C3	0.072751	0.242882	0.325382
C4	0.028341	0.153844	0.359738
C5	0.056871	0.107756	0.391145
C6	0.127651	0.149899	0.388313
C7	−0.042890	0.103281	0.357526
C8	−0.15025	0.17297	0.339684
C9	−0.216021	0.247734	0.356432
C10	−0.268313	0.238441	0.334853
C11	−0.252422	0.152158	0.296668
C12	−0.183893	0.079077	0.280439
C13	−0.133604	0.089167	0.30074
C14	−0.336327	0.312559	0.350286
C15	−0.386016	0.300825	0.329297
C16	−0.370391	0.214927	0.291764
C17	−0.304733	0.142302	0.275819
C18	−0.231823	0.339414	0.395593
C19	−0.285448	0.319527	0.446899
C20	−0.302214	0.410258	0.483286
C21	−0.265635	0.517652	0.468433
C22	−0.210477	0.542258	0.41697
C23	−0.194147	0.45214	0.380251
C24	−0.171798	0.652766	0.401095
C25	−0.118849	0.674557	0.350775
C26	−0.102778	0.585937	0.314176
C27	−0.139418	0.477861	0.328434
C28	−0.366996	0.166152	0.510124
C29	−0.404042	0.045823	0.515808
C30	−0.37175	−0.053278	0.484631
C31	−0.41315	−0.159891	0.496631
C32	−0.487591	−0.169504	0.540176
C33	−0.520208	−0.072965	0.572275
C34	−0.478194	0.032321	0.560254
Cl1	0.003662	−0.000121	0.435763
Cl2	−0.276993	−0.052010	0.430433
N1	−0.096069	0.186524	0.358286
N2	−0.321335	0.208491	0.461825
H1	−0.519488	−0.252897	0.549128
H2	−0.386013	−0.234849	0.471749
H3	−0.577911	−0.080018	0.606735
H4	−0.501337	0.108094	0.585179
H5	−0.171119	0.014168	0.250931
H6	−0.082026	0.031763	0.288514
H7	−0.410198	0.206668	0.275533
H8	−0.437836	0.358409	0.341701
H9	−0.291835	0.075924	0.246827
H10	−0.348683	0.379125	0.379043
H11	−0.343482	0.391482	0.522794
H12	−0.278947	0.585816	0.496783
H13	−0.127267	0.410654	0.299933
H14	−0.061305	0.60365	0.274325
H15	−0.185023	0.720259	0.429706
H16	−0.089531	0.759671	0.339008
H17	−0.307338	0.151455	0.432854
H18	−0.097148	0.264065	0.375093
H19	0.050874	0.278487	0.300849
H20	0.178039	0.35281	0.294659
H21	0.147962	0.113642	0.413476
H22	0.226858	0.269369	0.351252
O1	−0.048298	−0.001365	0.351095
O2	−0.38311	0.222257	0.548596

(20)

Crystal data

Monoclinic, P21/a	c = 13.1 Å
a = 12.3 Å	β = 77.3°
b = 17.6 Å	V = 2776.38 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.409446	0.716077	0.921938
C2	0.495371	0.664163	0.918093
C3	0.478019	0.587835	0.899235
C4	0.375216	0.562209	0.884351
C5	0.289736	0.615238	0.888643
C6	0.306777	0.69181	0.906665
C7	0.357999	0.478019	0.875577
C8	0.468044	0.367222	0.792891
C9	0.569147	0.347069	0.728224
C10	0.60712	0.270131	0.727968
C11	0.540112	0.214739	0.792077
C12	0.437169	0.237963	0.855108
C13	0.401289	0.311621	0.856079
C14	0.710872	0.246562	0.66573
C15	0.745355	0.172304	0.666714
C16	0.67835	0.117548	0.729693
C17	0.577804	0.138647	0.79113
C18	0.642334	0.404232	0.662641
C19	0.633884	0.416975	0.559735
C20	0.705736	0.469526	0.495626
C21	0.784806	0.507577	0.534197
C22	0.797477	0.49629	0.637589
C23	0.725752	0.443456	0.702182
C24	0.878623	0.535763	0.678316
C25	0.889078	0.523941	0.77905
C26	0.818424	0.471551	0.843169
C27	0.738972	0.432216	0.80586
C28	0.524139	0.383171	0.42755
C29	0.446765	0.322902	0.402804
C30	0.442406	0.245561	0.429783
C31	0.367194	0.196522	0.3983
C32	0.295117	0.223556	0.339024
C33	0.299382	0.299679	0.309382
C34	0.374974	0.347824	0.340457
Cl1	0.161112	0.587639	0.868015
Cl2	0.532953	0.204142	0.49864
N1	0.433593	0.443394	0.79638
N2	0.553268	0.376449	0.521869
H1	0.236652	0.184814	0.315335
H2	0.366792	0.137019	0.42013
H3	0.244421	0.321356	0.261966
H4	0.381297	0.40713	0.316995
H5	0.385407	0.195939	0.903752
H6	0.322629	0.329094	0.904576
H7	0.706634	0.059052	0.729492
H8	0.825097	0.155568	0.618483
H9	0.525357	0.097205	0.840281
H10	0.763098	0.288123	0.61692
H11	0.695543	0.479015	0.416924
H12	0.839326	0.547704	0.484549
H13	0.685628	0.391465	0.855277
H14	0.827361	0.461941	0.922622
H15	0.932662	0.575788	0.627989
H16	0.951655	0.554497	0.809483
H17	0.515399	0.335056	0.570465
H18	0.484402	0.478714	0.746667
H19	0.544831	0.546982	0.896404
H20	0.575639	0.682832	0.929856
H21	0.239452	0.731855	0.908473
H22	0.421945	0.775887	0.936442
O1	0.286047	0.444997	0.938317
O2	0.555182	0.434531	0.365316

(21)

Crystal data

Monoclinic, I2/c	c = 18.5 Å
a = 19.0 Å	β = 84.8°
b = 15.6 Å	V = 5483.38 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.565481	0.7051	0.849506
C2	0.578042	0.770856	0.799338
C3	0.597203	0.750987	0.727387
C4	0.605332	0.666383	0.70248
C5	0.591324	0.601498	0.75419
C6	0.571775	0.620617	0.826717
C7	0.625726	0.659788	0.621787
C8	0.682718	0.56685	0.525071
C9	0.694931	0.480652	0.508445
C10	0.718073	0.456235	0.435905
C11	0.727823	0.520156	0.380889
C12	0.714416	0.606603	0.400289
C13	0.692605	0.629985	0.469978
C14	0.731551	0.369544	0.416184
C15	0.753454	0.347803	0.345901
C16	0.763092	0.411232	0.291609
C17	0.750451	0.495622	0.308964
C18	0.684418	0.41378	0.565934
C19	0.739292	0.391895	0.607543
C20	0.728607	0.327852	0.661973
C21	0.664549	0.288004	0.673815
C22	0.607412	0.308357	0.633069
C23	0.617566	0.372475	0.578289
C24	0.541014	0.26748	0.645297
C25	0.48644	0.288903	0.60512
C26	0.496331	0.352365	0.550879
C27	0.560137	0.393121	0.537676
C28	0.86125	0.431168	0.63291
C29	0.924472	0.487101	0.60999
C30	0.931307	0.557453	0.562726
C31	0.994832	0.601684	0.550209
C32	1.05336	0.576805	0.584546
C33	1.04814	0.507648	0.632065
C34	0.98465	0.464464	0.644302
Cl1	0.593983	0.492866	0.732499
Cl2	0.861906	0.597149	0.517
N1	0.661747	0.587967	0.597481
N2	0.80482	0.432381	0.592206
H1	1.10258	0.611717	0.574218
H2	0.997484	0.655869	0.513441
H3	1.09331	0.487495	0.65964
H4	0.978891	0.410974	0.681692
H5	0.721787	0.655561	0.358581
H6	0.681684	0.696109	0.484138
H7	0.780438	0.393038	0.236279
H8	0.763411	0.28109	0.331894
H9	0.757638	0.545105	0.267676
H10	0.724043	0.320385	0.457584
H11	0.771823	0.311852	0.6935
H12	0.657174	0.23911	0.715587
H13	0.567327	0.441837	0.495874
H14	0.45297	0.369146	0.519266
H15	0.534125	0.218769	0.687267
H16	0.435665	0.257277	0.6149
H17	0.807554	0.472104	0.548838
H18	0.664813	0.539258	0.633127
H19	0.606233	0.801028	0.686988
H20	0.572811	0.83732	0.816088
H21	0.561149	0.568339	0.864676
H22	0.550318	0.71912	0.906186
O1	0.61287	0.719701	0.582638
O2	0.863871	0.385655	0.68638

(22)

Crystal data

Triclinic, P1	α = 98.7°
a = 12.1 Å	β = 93.5°
b = 11.2 Å	γ = 73.7°
c = 11.0 Å	V = 1413.98 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.825228	0.180305	0.561922
C2	0.844752	0.133676	0.437871
C3	0.868163	0.208938	0.359591
C4	0.870795	0.332427	0.400437
C5	0.852737	0.376379	0.526321
C6	0.830295	0.301066	0.606155
C7	0.897063	0.400054	0.30204
C8	0.862504	0.612243	0.241154
C9	0.783642	0.730496	0.252418
C10	0.7984	0.821489	0.18153
C11	0.893424	0.790302	0.100375
C12	0.971911	0.669478	0.093715
C13	0.957993	0.582606	0.161817
C14	0.72058	0.943172	0.188422
C15	0.736014	1.0284	0.118262
C16	0.829924	0.997086	0.037873
C17	0.906983	0.880304	0.029493
C18	0.684572	0.764506	0.337679
C19	0.576563	0.755163	0.292862
C20	0.480785	0.789965	0.372232
C21	0.493879	0.834393	0.493856
C22	0.601186	0.84777	0.54353
C23	0.697648	0.813084	0.464024
C24	0.615047	0.895247	0.668845
C25	0.719675	0.909084	0.714497
C26	0.815033	0.8761	0.635781
C27	0.804518	0.829244	0.51385
C28	0.465915	0.725933	0.096383
C29	0.488939	0.672863	−0.036865
C30	0.414686	0.614095	−0.109667
C31	0.43649	0.570135	−0.233941
C32	0.531758	0.585347	−0.287988
C33	0.606087	0.644148	−0.217755
C34	0.584443	0.686924	−0.093664
Cl1	0.861346	0.524584	0.593151
Cl2	0.296144	0.587143	−0.048959
N1	0.846881	0.526298	0.313898
N2	0.564961	0.710852	0.167926
H1	0.54745	0.551146	−0.38511
H2	0.378179	0.52374	−0.287353
H3	0.680248	0.657431	−0.259226
H4	0.640771	0.736509	−0.040404
H5	1.04507	0.645727	0.032965
H6	1.01732	0.489826	0.154917
H7	0.841066	1.06551	−0.016851
H8	0.675369	1.12096	0.124905
H9	0.979959	0.855025	−0.031709
H10	0.648375	0.968337	0.250386
H11	0.398051	0.782319	0.334042
H12	0.420194	0.860597	0.554137
H13	0.878197	0.804373	0.453877
H14	0.897466	0.888112	0.671978
H15	0.540781	0.920891	0.728275
H16	0.729324	0.945721	0.810742
H17	0.639902	0.666728	0.124505
H18	0.791284	0.564338	0.38376
H19	0.885488	0.174261	0.262873
H20	0.842244	0.038957	0.40237
H21	0.817552	0.338178	0.702985
H22	0.807022	0.122734	0.624865
O1	0.957858	0.340875	0.215924
O2	0.369324	0.777734	0.134768

(23)

Crystal data

Monoclinic, P21/n	c = 10.9 Å
a = 14.4 Å	β = 70.8°
b = 19.0 Å	V = 2828.01 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.614796	0.679819	0.781768
C2	0.555323	0.738961	0.819218
C3	0.567311	0.795103	0.734193
C4	0.638132	0.793388	0.610815
C5	0.696947	0.733532	0.574828
C6	0.685956	0.677076	0.659681
C7	0.647978	0.856866	0.524846
C8	0.617173	0.896407	0.325318
C9	0.63129	0.873297	0.199945
C10	0.628372	0.923542	0.103312
C11	0.612923	0.996113	0.136633
C12	0.600187	1.0168	0.265717
C13	0.60164	0.968662	0.357987
C14	0.641237	0.903495	−0.026440
C15	0.638729	0.952643	−0.117541
C16	0.623346	1.02435	−0.084152
C17	0.610766	1.04545	0.040562
C18	0.651132	0.798239	0.161201
C19	0.747369	0.773615	0.11236
C20	0.766245	0.702656	0.071191
C21	0.689981	0.658466	0.077237
C22	0.591269	0.681451	0.122893
C23	0.571788	0.752664	0.164416
C24	0.512096	0.636313	0.127853
C25	0.416968	0.660155	0.171842
C26	0.397393	0.730621	0.212656
C27	0.47259	0.775707	0.209275
C28	0.922542	0.809748	0.056286
C29	0.987315	0.872222	0.054215
C30	0.976807	0.923253	0.15029
C31	1.04635	0.976328	0.134728
C32	1.12742	0.979453	0.022582
C33	1.13994	0.928912	−0.073774
C34	1.07102	0.87583	−0.056723
Cl1	0.786945	0.728368	0.42305
Cl2	0.878483	0.923067	0.295121
N1	0.613879	0.847313	0.423016
N2	0.823453	0.820921	0.104259
H1	1.18098	1.02117	0.011258
H2	1.03616	1.01461	0.21168
H3	1.20348	0.930588	−0.161386
H4	1.08042	0.834814	−0.128859
H5	0.58855	1.07206	0.291344
H6	0.592652	0.984647	0.456355
H7	0.621525	1.06261	−0.15715
H8	0.648623	0.936095	−0.216275
H9	0.598911	1.10054	0.067640
H10	0.652973	0.848445	−0.053036
H11	0.841614	0.684974	0.034839
H12	0.705372	0.604253	0.045642
H13	0.456907	0.829923	0.240244
H14	0.322074	0.749399	0.246912
H15	0.528262	0.582215	0.095873
H16	0.356767	0.625099	0.175181
H17	0.800972	0.869451	0.139582
H18	0.595303	0.79765	0.407598
H19	0.522066	0.841811	0.76306
H20	0.499739	0.741384	0.914551
H21	0.733341	0.631605	0.629216
H22	0.60626	0.635674	0.847604
O1	0.680003	0.912227	0.550446
O2	0.960565	0.753983	0.010736

(24)

Crystal data

Monoclinic, P21/a	c = 12.3 Å
a = 15.3 Å	β = 75.1°
b = 15.3 Å	V = 2779.8 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.63645	0.981944	0.518543
C2	0.675081	1.02757	0.419867
C3	0.656182	1.00236	0.319958
C4	0.596746	0.933505	0.315653
C5	0.559619	0.887964	0.415768
C6	0.579338	0.911883	0.516317
C7	0.586246	0.91473	0.199101
C8	0.475104	0.869287	0.093549
C9	0.390881	0.829998	0.105996
C10	0.360478	0.809019	0.008445
C11	0.416572	0.828476	−0.100839
C12	0.501013	0.869095	−0.109033
C13	0.530049	0.889357	−0.015553
C14	0.275516	0.76868	0.016317
C15	0.248209	0.748697	−0.078889
C16	0.303963	0.767931	−0.18688
C17	0.386407	0.807078	−0.19728
C18	0.331028	0.81123	0.220082
C19	0.336193	0.732589	0.274734
C20	0.277467	0.715421	0.382423
C21	0.215154	0.776758	0.433078
C22	0.206993	0.857729	0.380922
C23	0.265564	0.875183	0.272435
C24	0.142542	0.921236	0.433122
C25	0.13568	0.999213	0.380695
C26	0.193422	1.01662	0.273359
C27	0.256688	0.956348	0.220455
C28	0.429631	0.597641	0.263477
C29	0.497751	0.546388	0.177064
C30	0.489732	0.455896	0.165365
C31	0.554432	0.409514	0.086088
C32	0.628226	0.452807	0.017695
C33	0.637204	0.542674	0.027598
C34	0.571982	0.588676	0.106244
Cl1	0.490692	0.796623	0.420835
Cl2	0.397898	0.398216	0.245396
N1	0.502213	0.889714	0.191306
N2	0.399971	0.671078	0.219649
H1	0.67852	0.415933	−0.043519
H2	0.546122	0.339593	0.078364
H3	0.69467	0.576958	−0.025337
H4	0.579573	0.658734	0.1153
H5	0.543739	0.884658	−0.192051
H6	0.594971	0.919853	−0.022656
H7	0.281407	0.751746	−0.261349
H8	0.182969	0.717818	−0.071026
H9	0.429977	0.822342	−0.279919
H10	0.232112	0.753859	0.099025
H11	0.283915	0.653929	0.42302
H12	0.170445	0.763239	0.515568
H13	0.30058	0.970206	0.13774
H14	0.187683	1.07833	0.23206
H15	0.098452	0.906934	0.515766
H16	0.085988	1.04751	0.421402
H17	0.42716	0.68271	0.136825
H18	0.454492	0.879137	0.264171
H19	0.687239	1.03531	0.241344
H20	0.720571	1.08186	0.420545
H21	0.550078	0.874535	0.591929
H22	0.651097	1.00026	0.597424
O1	0.650789	0.926337	0.118
O2	0.404573	0.575105	0.361649

(25)

Crystal data

Triclinic, P1	α = 64.4°
a = 13.8 Å	β = 77.1°
b = 10.3 Å	γ = 96.2°
c = 11.6 Å	V = 1402.52 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.173127	0.626313	0.471166
C2	0.201653	0.700642	0.331811
C3	0.181743	0.623604	0.263003
C4	0.133007	0.472575	0.330724
C5	0.102977	0.400663	0.471146
C6	0.124087	0.476332	0.540821
C7	0.10279	0.398976	0.252519
C8	0.169015	0.325923	0.081599
C9	0.233234	0.235447	0.066572
C10	0.213715	0.154324	−0.003600
C11	0.129155	0.167551	−0.056417
C12	0.065547	0.260203	−0.037016
C13	0.083967	0.33618	0.030950
C14	0.274779	0.057123	−0.020200
C15	0.25405	−0.020105	−0.087010
C16	0.171288	−0.004829	−0.140805
C17	0.110069	0.08697	−0.125205
C18	0.320201	0.217009	0.124536
C19	0.421003	0.279346	0.041965
C20	0.502891	0.254391	0.098319
C21	0.482983	0.169469	0.233784
C22	0.382126	0.102759	0.321199
C23	0.299142	0.1259	0.265683
C24	0.36187	0.012076	0.460836
C25	0.263451	−0.055180	0.543219
C26	0.181258	−0.033897	0.488473
C27	0.198319	0.054318	0.353553
C28	0.526108	0.466703	−0.187108
C29	0.525552	0.558376	−0.329809
C30	0.444591	0.607739	−0.377689
C31	0.458493	0.696307	−0.51381
C32	0.554254	0.738262	−0.606089
C33	0.636469	0.693096	−0.561628
C34	0.621609	0.605992	−0.425842
Cl1	0.039874	0.214507	0.563742
Cl2	0.321337	0.567299	−0.271321
N1	0.182675	0.403838	0.153747
N2	0.438338	0.364947	−0.096743
H1	0.564323	0.806922	−0.712044
H2	0.393659	0.732271	−0.545893
H3	0.712061	0.726108	−0.632368
H4	0.684891	0.571682	−0.388525
H5	0.000763	0.269916	−0.076496
H6	0.034382	0.405614	0.046592
H7	0.155925	−0.066332	−0.193594
H8	0.301725	−0.094100	−0.098084
H9	0.045462	0.098939	−0.165059
H10	0.338122	0.043229	0.021743
H11	0.580293	0.304897	0.032634
H12	0.546337	0.151435	0.275731
H13	0.134196	0.069267	0.313134
H14	0.103465	−0.087594	0.553766
H15	0.426065	−0.003873	0.501308
H16	0.248534	−0.12492	0.650183
H17	0.374811	0.367821	−0.126781
H18	0.253295	0.423755	0.162704
H19	0.203372	0.680963	0.154098
H20	0.239118	0.818028	0.276727
H21	0.101241	0.41696	0.649532
H22	0.188528	0.684697	0.526459
O1	0.013759	0.345481	0.273195
O2	0.60628	0.482243	−0.160882

(26)

Crystal data

Triclinic, P1	α = 61.8°
a = 15.0 Å	β = 61.1°
b = 10.4 Å	γ = 74.8°
c = 11.6 Å	V = 1392.63 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.568402	0.897902	0.187447
C2	0.63696	0.909924	0.048289
C3	0.614823	0.849992	−0.018884
C4	0.524241	0.778483	0.048935
C5	0.457554	0.764842	0.190139
C6	0.479344	0.824406	0.258664
C7	0.515397	0.718253	−0.040737
C8	0.393264	0.668373	−0.100971
C9	0.290167	0.660239	−0.059751
C10	0.260747	0.611238	−0.132227
C11	0.337329	0.572439	−0.247118
C12	0.440899	0.585769	−0.287075
C13	0.469199	0.632864	−0.217693
C14	0.156847	0.599751	−0.093876
C15	0.130729	0.551613	−0.165039
C16	0.20668	0.512758	−0.278268
C17	0.307811	0.523248	−0.318236
C18	0.210565	0.707032	0.056025
C19	0.174522	0.610345	0.201014
C20	0.098531	0.656473	0.310236
C21	0.060422	0.797199	0.274091
C22	0.095179	0.900645	0.12839
C23	0.170948	0.8547	0.018393
C24	0.057052	1.04706	0.089555
C25	0.092010	1.14538	−0.052702
C26	0.166888	1.10035	−0.161983
C27	0.205291	0.958871	−0.127608
C28	0.198112	0.363713	0.375897
C29	0.204822	0.206966	0.401537
C30	0.146425	0.148723	0.374369
C31	0.149853	−0.000518	0.414543
C32	0.211423	−0.093340	0.483234
C33	0.268285	−0.037897	0.514275
C34	0.26332	0.11057	0.475544
Cl1	0.347297	0.666668	0.291881
Cl2	0.065296	0.258211	0.292463
N1	0.42008	0.719271	−0.029644
N2	0.212153	0.465215	0.239264
H1	0.213986	−0.209463	0.51372
H2	0.103571	−0.042584	0.392427
H3	0.315464	−0.110279	0.569615
H4	0.304794	0.15589	0.502019
H5	0.499349	0.558107	−0.375823
H6	0.548452	0.642001	−0.248328
H7	0.18485	0.474887	−0.333522
H8	0.050799	0.543497	−0.134015
H9	0.367047	0.49398	−0.405471
H10	0.098005	0.629818	−0.007176
H11	0.072675	0.579206	0.422299
H12	0.002310	0.831092	0.35864
H13	0.262636	0.925036	−0.212418
H14	0.194345	1.17827	−0.274467
H15	−0.000667	1.08013	0.174951
H16	0.062232	1.25749	−0.081394
H17	0.242643	0.427971	0.160768
H18	0.360647	0.7493	0.046617
H19	0.667644	0.85541	−0.126169
H20	0.707399	0.965595	−0.007490
H21	0.426302	0.811004	0.368382
H22	0.584535	0.944068	0.2418
O1	0.593585	0.678175	−0.123101
O2	0.180623	0.393903	0.475129

(27)

Crystal data

Monoclinic, C2/c	c = 30.2 Å
a = 10.9 Å	β = 117.6°
b = 19.2 Å	V = 5605.18 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.420378	0.968135	0.057301
C2	0.564257	0.969938	0.083955
C3	0.642442	0.934761	0.065743
C4	0.581424	0.89777	0.020541
C5	0.436291	0.896099	−0.005232
C6	0.356707	0.930875	0.012968
C7	0.686996	0.863624	0.008131
C8	0.726833	0.813674	−0.060129
C9	0.66248	0.796903	−0.110853
C10	0.740485	0.765091	−0.132489
C11	0.883644	0.750005	−0.101831
C12	0.944215	0.767765	−0.050575
C13	0.869722	0.798899	−0.029908
C14	0.680368	0.748063	−0.18408
C15	0.757969	0.717477	−0.203895
C16	0.899395	0.702238	−0.173389
C17	0.960608	0.718312	−0.123404
C18	0.512798	0.812803	−0.142713
C19	0.410136	0.764899	−0.149169
C20	0.268159	0.781423	−0.17969
C21	0.230996	0.844585	−0.202941
C22	0.331074	0.895253	−0.197423
C23	0.473599	0.878937	−0.167003
C24	0.293706	0.960974	−0.221016
C25	0.393029	1.00923	−0.215047
C26	0.534298	0.99328	−0.185066
C27	0.573734	0.929908	−0.161702
C28	0.361922	0.648055	−0.125911
C29	0.42018	0.575607	−0.114728
C30	0.473283	0.539905	−0.142445
C31	0.511904	0.470329	−0.132717
C32	0.497262	0.435653	−0.095072
C33	0.442175	0.469936	−0.067641
C34	0.402305	0.538934	−0.078088
Cl1	0.343793	0.849243	−0.060385
Cl2	0.491421	0.580422	−0.190684
N1	0.647595	0.846624	−0.040567
N2	0.448378	0.699964	−0.125539
H1	0.527984	0.381488	−0.087539
H2	0.552319	0.443937	−0.154966
H3	0.429175	0.442747	−0.038577
H4	0.355568	0.566079	−0.058140
H5	1.05334	0.756519	−0.027082
H6	0.917113	0.812477	0.009249
H7	0.959338	0.677983	−0.189596
H8	0.710117	0.704988	−0.24348
H9	1.06952	0.707057	−0.099518
H10	0.571814	0.759843	−0.207811
H11	0.190539	0.743593	−0.183466
H12	0.122013	0.856418	−0.226137
H13	0.682689	0.918073	−0.138834
H14	0.612729	1.03149	−0.180466
H15	0.184448	0.972432	−0.244025
H16	0.363406	1.05952	−0.233309
H17	0.549114	0.687106	−0.112971
H18	0.547843	0.855691	−0.065815
H19	0.754642	0.934437	0.086001
H20	0.615333	0.998445	0.118881
H21	0.244734	0.927967	−0.007949
H22	0.357212	0.995223	0.070993
O1	0.804298	0.854748	0.042029
O2	0.242202	0.657242	−0.134299

(28)

Crystal data

Triclinic, P1	α = 81.6°
a = 11.3 Å	β = 87.5°
b = 10.9 Å	γ = 96.8°
c = 11.8 Å	V = 1424.21 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.851639	0.193947	0.675585
C2	0.854094	0.069796	0.659681
C3	0.96238	0.027539	0.637161
C4	1.06947	0.107783	0.629048
C5	1.06503	0.232544	0.645305
C6	0.956924	0.275101	0.668896
C7	1.18362	0.059926	0.597499
C8	1.27793	−0.137802	0.639351
C9	1.27404	−0.247545	0.718268
C10	1.35679	−0.33433	0.703005
C11	1.44351	−0.306783	0.608465
C12	1.44356	−0.194336	0.530835
C13	1.36352	−0.112001	0.544684
C14	1.35671	−0.44802	0.779775
C15	1.43868	−0.528623	0.764103
C16	1.52483	−0.500573	0.670957
C17	1.52666	−0.391857	0.594692
C18	1.18481	−0.275152	0.818279
C19	1.22054	−0.257861	0.927096
C20	1.13809	−0.28607	1.02411
C21	1.02227	−0.330576	1.01112
C22	0.981647	−0.350289	0.902712
C23	1.06444	−0.323243	0.80499
C24	0.862005	−0.396424	0.88881
C25	0.824733	−0.415623	0.782898
C26	0.906608	−0.389966	0.686201
C27	1.02339	−0.345083	0.696744
C28	1.40318	−0.221329	1.03412
C29	1.53299	−0.173879	1.00918
C30	1.60032	−0.112589	1.08616
C31	1.72148	−0.074263	1.06232
C32	1.77794	−0.097790	0.962164
C33	1.71324	−0.159412	0.885108
C34	1.59229	−0.196511	0.908873
Cl1	1.19326	0.337584	0.641613
Cl2	1.53669	−0.075319	1.21122
N1	1.19362	−0.057190	0.656011
N2	1.33935	−0.212375	0.937361
H1	1.87256	−0.067887	0.944859
H2	1.77055	−0.025625	1.12295
H3	1.75646	−0.17941	0.807087
H4	1.54353	−0.248694	0.85011
H5	1.50914	−0.173212	0.458454
H6	1.3648	−0.025422	0.485854
H7	1.58899	−0.565229	0.65971
H8	1.43699	−0.615012	0.823971
H9	1.59203	−0.36932	0.522153
H10	1.2905	−0.470936	0.851393
H11	1.16919	−0.272802	1.10737
H12	0.959425	−0.351414	1.08568
H13	1.08617	−0.326999	0.622244
H14	0.877153	−0.406687	0.602762
H15	0.80005	−0.416545	0.964072
H16	0.732766	−0.451129	0.773277
H17	1.38484	−0.173789	0.862582
H18	1.13263	−0.090189	0.721849
H19	0.964285	−0.069158	0.623561
H20	0.772284	0.005900	0.664707
H21	0.956326	0.371815	0.682244
H22	0.767742	0.228299	0.693536
O1	1.25572	0.117672	0.523413
O2	1.36072	−0.265732	1.12999

(29)

Crystal data

Triclinic, P1	α = 77.9°
a = 11.2 Å	β = 123.5°
b = 10.1 Å	γ = 116.9°
c = 16.7 Å	V = 1392.66 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.658069	0.203569	0.363129
C2	0.508122	0.11238	0.291318
C3	0.381248	0.064808	0.303074
C4	0.399615	0.108603	0.385023
C5	0.551814	0.200658	0.456479
C6	0.679825	0.247218	0.445572
C7	0.258277	0.056954	0.393856
C8	0.006463	−0.166542	0.351295
C9	−0.110312	−0.279665	0.279409
C10	−0.256393	−0.369303	0.274701
C11	−0.280719	−0.341254	0.343863
C12	−0.158127	−0.225072	0.4158
C13	−0.017812	−0.140093	0.420409
C14	−0.379697	−0.485564	0.202741
C15	−0.51933	−0.569465	0.199789
C16	−0.543023	−0.541816	0.268423
C17	−0.425918	−0.429861	0.338871
C18	−0.080705	−0.307027	0.20866
C19	−0.101824	−0.221844	0.128263
C20	−0.069737	−0.247467	0.062840
C21	−0.019466	−0.356727	0.078186
C22	0.002419	−0.446614	0.158345
C23	−0.028459	−0.421136	0.224891
C24	0.054129	−0.559783	0.174333
C25	0.075243	−0.644855	0.253042
C26	0.045221	−0.619731	0.319142
C27	−0.005117	−0.510851	0.305689
C28	−0.220688	−0.044349	0.032137
C29	−0.2716	0.071046	0.033212
C30	−0.29614	0.101955	0.099966
C31	−0.347305	0.212554	0.085817
C32	−0.375644	0.295139	0.004505
C33	−0.353894	0.26612	−0.063449
C34	−0.303702	0.155509	−0.048812
Cl1	0.590817	0.256297	0.563136
Cl2	−0.268413	0.005431	0.204468
N1	0.150922	−0.085796	0.356086
N2	−0.152376	−0.110527	0.11582
H1	−0.41511	0.381218	−0.005500
H2	−0.36477	0.232392	0.139321
H3	−0.376313	0.329116	−0.12774
H4	−0.287718	0.129239	−0.101169
H5	−0.176363	−0.204206	0.468783
H6	0.074957	−0.050328	0.474815
H7	−0.653986	−0.609167	0.265227
H8	−0.612517	−0.657956	0.144081
H9	−0.442893	−0.407378	0.392037
H10	−0.362127	−0.507224	0.149747
H11	−0.088690	−0.181311	0.000400
H12	0.004261	−0.375477	0.027440
H13	−0.028458	−0.492807	0.356729
H14	0.062019	−0.687363	0.381297
H15	0.076865	−0.577942	0.122896
H16	0.114932	−0.731414	0.264691
H17	−0.151224	−0.088794	0.172912
H18	0.178356	−0.1414	0.32926
H19	0.263904	−0.003161	0.245407
H20	0.48964	0.078220	0.226401
H21	0.796247	0.317326	0.502536
H22	0.758722	0.241281	0.355302
O1	0.239633	0.135497	0.42864
O2	−0.240876	−0.073201	−0.043267

(30)

Crystal data

Triclinic, P1	α = 84.7°
a = 10.7 Å	β = 67.1°
b = 14.6 Å	γ = 96.1°
c = 9.8 Å	V = 1396.9 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.107215	0.988157	0.18767
C2	0.20251	1.05435	0.073874
C3	0.238688	1.0403	−0.072928
C4	0.183719	0.960779	−0.112863
C5	0.087839	0.895273	0.004398
C6	0.050013	0.908931	0.152554
C7	0.238425	0.961645	−0.28014
C8	0.255782	0.868956	−0.483052
C9	0.189781	0.7911	−0.514007
C10	0.226185	0.774696	−0.664278
C11	0.329606	0.838729	−0.782526
C12	0.393719	0.916704	−0.746084
C13	0.358967	0.932012	−0.601636
C14	0.162318	0.696245	−0.701042
C15	0.199181	0.68244	−0.846823
C16	0.301551	0.745969	−0.963556
C17	0.365163	0.822497	−0.93159
C18	0.082768	0.723848	−0.389665
C19	0.118001	0.651254	−0.317055
C20	0.014480	0.587813	−0.199458
C21	−0.120528	0.598041	−0.157267
C22	−0.161307	0.670793	−0.227928
C23	−0.057965	0.734812	−0.346222
C24	−0.300795	0.681617	−0.184302
C25	−0.337518	0.752924	−0.254448
C26	−0.235483	0.816411	−0.371419
C27	−0.099232	0.80771	−0.416403
C28	0.317664	0.595637	−0.287584
C29	0.467579	0.58658	−0.365369
C30	0.57158	0.641817	−0.490367
C31	0.705508	0.622373	−0.545543
C32	0.738727	0.547075	−0.477131
C33	0.637976	0.491659	−0.351988
C34	0.505372	0.512019	−0.297603
Cl1	0.005609	0.793076	−0.022029
Cl2	0.544494	0.740462	−0.583022
N1	0.217903	0.880729	−0.333235
N2	0.257236	0.641632	−0.366749
H1	0.843366	0.532449	−0.521384
H2	0.782963	0.667232	−0.641877
H3	0.662665	0.432945	−0.296673
H4	0.425209	0.470911	−0.198967
H5	0.47282	0.965656	−0.83563
H6	0.407695	0.992426	−0.575442
H7	0.329562	0.734094	−1.07827
H8	0.148958	0.622065	−0.872677
H9	0.444144	0.871965	−1.0204
H10	0.083160	0.647262	−0.611962
H11	0.044501	0.532795	−0.143293
H12	−0.199089	0.549086	−0.067217
H13	−0.021375	0.856773	−0.50651
H14	−0.265043	0.872758	−0.426474
H15	−0.378357	0.632299	−0.093928
H16	−0.44479	0.760718	−0.220257
H17	0.31888	0.676687	−0.46866
H18	0.154952	0.826136	−0.258483
H19	0.311348	1.09124	−0.163994
H20	0.248227	1.1168	0.099278
H21	−0.024937	0.856636	0.239422
H22	0.076966	0.9978	0.303584
O1	0.30196	1.03416	−0.361593
O2	0.254819	0.55899	−0.158088

(31)

Crystal data

Monoclinic, C2/c	c = 27.1 Å
a = 10.9 Å	β = 96.8°
b = 19.1 Å	V = 5602.71 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.148572	0.686322	0.599065
C2	0.229235	0.718388	0.569896
C3	0.26247	0.787849	0.578636
C4	0.215534	0.827004	0.6158
C5	0.134755	0.793651	0.64471
C6	0.101937	0.723673	0.636659
C7	0.26041	0.901146	0.623009
C8	0.189344	1.01788	0.647804
C9	0.094014	1.06654	0.641539
C10	0.108356	1.13259	0.666477
C11	0.220521	1.14798	0.697151
C12	0.314593	1.09649	0.702448
C13	0.300504	1.03317	0.678795
C14	0.013958	1.18413	0.66165
C15	0.030426	1.24736	0.68578
C16	0.14166	1.2625	0.715987
C17	0.234641	1.2136	0.721474
C18	−0.024003	1.05013	0.610027
C19	−0.037338	1.06666	0.559473
C20	−0.149905	1.05181	0.52929
C21	−0.245691	1.02106	0.549532
C22	−0.236854	1.00348	0.600452
C23	−0.124431	1.01854	0.631064
C24	−0.335694	0.97197	0.621733
C25	−0.32488	0.956017	0.671421
C26	−0.214013	0.971196	0.701923
C27	−0.116374	1.00162	0.682373
C28	0.072608	1.11435	0.49153
C29	0.19113	1.14788	0.479419
C30	0.311153	1.14365	0.504275
C31	0.409778	1.17763	0.486234
C32	0.390779	1.21658	0.442778
C33	0.272972	1.22079	0.416895
C34	0.175783	1.18643	0.435015
Cl1	0.075520	0.836722	0.693366
Cl2	0.347734	1.09379	0.557951
N1	0.172688	0.952108	0.624863
N2	0.062809	1.09792	0.539971
H1	0.468261	1.24298	0.429138
H2	0.501193	1.17262	0.506523
H3	0.256945	1.25052	0.382602
H4	0.083461	1.18791	0.41519
H5	0.39992	1.10784	0.726051
H6	0.373745	0.994695	0.68264
H7	0.153305	1.3127	0.734832
H8	−0.043020	1.28611	0.681597
H9	0.320767	1.22451	0.744684
H10	−0.071993	1.17283	0.638568
H11	−0.157486	1.06505	0.490314
H12	−0.331126	1.00987	0.525949
H13	−0.031573	1.01337	0.706086
H14	−0.205988	0.958784	0.741275
H15	−0.420629	0.960768	0.597828
H16	−0.401281	0.93191	0.687394
H17	0.138125	1.10587	0.564967
H18	0.083979	0.938047	0.614491
H19	0.327006	0.813535	0.556974
H20	0.266353	0.689332	0.540612
H21	0.040414	0.699087	0.660121
H22	0.122137	0.631878	0.592844
O1	0.37123	0.912782	0.627132
O2	−0.010926	1.1059	0.457747

(32)

Crystal data

Triclinic, P1	α = 120.4°
a = 11.1 Å	β = 58.9°
b = 17.4 Å	γ = 99.6°
c = 9.9 Å	V = 1408.14 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.731791	0.372691	0.270288
C2	0.589531	0.365397	0.370147
C3	0.516434	0.418491	0.557442
C4	0.580884	0.481224	0.650418
C5	0.724617	0.486354	0.547201
C6	0.799633	0.432588	0.358986
C7	0.484953	0.533239	0.85353
C8	0.421299	0.685996	1.12293
C9	0.440701	0.775607	1.17349
C10	0.360532	0.843286	1.35995
C11	0.26001	0.818701	1.49137
C12	0.244421	0.726958	1.43304
C13	0.322089	0.662022	1.25503
C14	0.377467	0.935338	1.42014
C15	0.29825	0.999046	1.59988
C16	0.198267	0.97449	1.72928
C17	0.179978	0.88597	1.67556
C18	0.550387	0.801739	1.03906
C19	0.692546	0.794408	0.988287
C20	0.795362	0.820588	0.861203
C21	0.75551	0.854655	0.790689
C22	0.612495	0.864652	0.839808
C23	0.509055	0.837652	0.965318
C24	0.570039	0.899965	0.767836
C25	0.43044	0.908338	0.817084
C26	0.327633	0.881328	0.940767
C27	0.365689	0.846824	1.01287
C28	0.860896	0.764105	1.05517
C29	0.874214	0.721825	1.14706
C30	0.937279	0.762507	1.25409
C31	0.965091	0.717251	1.31897
C32	0.933762	0.62997	1.27406
C33	0.873588	0.587876	1.16532
C34	0.844829	0.633741	1.10233
Cl1	0.820598	0.556803	0.646598
Cl2	0.975408	0.87199	1.31918
N1	0.500644	0.621749	0.938492
N2	0.733504	0.760305	1.06177
H1	0.956923	0.595085	1.32439
H2	1.01149	0.750922	1.40434
H3	0.850053	0.519501	1.12836
H4	0.800488	0.60058	1.01418
H5	0.168612	0.707819	1.53285
H6	0.308278	0.592147	1.21121
H7	0.136453	1.02565	1.87087
H8	0.312857	1.06912	1.64294
H9	0.103768	0.865993	1.77377
H10	0.454087	0.954999	1.32189
H11	0.90472	0.814358	0.824451
H12	0.835543	0.87455	0.694264
H13	0.285851	0.826211	1.10786
H14	0.21727	0.887854	0.979275
H15	0.650539	0.920283	0.672418
H16	0.398839	0.935525	0.761194
H17	0.654518	0.740849	1.14685
H18	0.572496	0.646454	0.859018
H19	0.406237	0.412901	0.638555
H20	0.535914	0.318134	0.302281
H21	0.911124	0.43797	0.283899
H22	0.790809	0.33137	0.1235
O1	0.3945	0.496305	0.930024
O2	0.961272	0.794935	0.974937

(33)

Crystal data

Monoclinic, P21/n	c = 14.6 Å
a = 10.8 Å	β = 71.0°
b = 18.9 Å	V = 2814.57 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.666752	0.027273	0.649583
C2	0.566594	0.075685	0.658213
C3	0.581751	0.126865	0.587015
C4	0.69318	0.128848	0.504132
C5	0.791591	0.079065	0.496152
C6	0.778966	0.028816	0.568887
C7	0.697261	0.190361	0.437141
C8	0.738365	0.220938	0.26344
C9	0.793549	0.195752	0.168871
C10	0.806543	0.242038	0.088580
C11	0.763016	0.313588	0.106179
C12	0.706455	0.336366	0.203532
C13	0.693616	0.291972	0.280442
C14	0.862164	0.219295	−0.009291
C15	0.874127	0.265086	−0.085044
C16	0.831359	0.335898	−0.067355
C17	0.776833	0.359432	0.026480
C18	0.836857	0.120657	0.15047
C19	0.96056	0.099869	0.149146
C20	1.00086	0.028208	0.13112
C21	0.918492	−0.020585	0.112773
C22	0.792932	−0.001778	0.110754
C23	0.751455	0.070004	0.129744
C24	0.708086	−0.051806	0.090309
C25	0.58704	−0.032043	0.088311
C26	0.545815	0.038928	0.107062
C27	0.625662	0.088693	0.127438
C28	1.16264	0.144649	0.176766
C29	1.23324	0.213159	0.178309
C30	1.1897	0.26792	0.245706
C31	1.26681	0.327449	0.242828
C32	1.38842	0.333068	0.17167
C33	1.43383	0.278952	0.104046
C34	1.35715	0.219417	0.108442
Cl1	0.936551	0.079227	0.398678
Cl2	1.03814	0.263578	0.336241
N1	0.725772	0.174076	0.340757
N2	1.04468	0.152078	0.162608
H1	1.44783	0.379715	0.169597
H2	1.23052	0.368776	0.296646
H3	1.52911	0.282873	0.048625
H4	1.39242	0.17595	0.057866
H5	0.672315	0.390698	0.217233
H6	0.65138	0.30994	0.354612
H7	0.841513	0.371484	−0.127993
H8	0.916889	0.246594	−0.159387
H9	0.743208	0.413793	0.041155
H10	0.895005	0.164876	−0.023698
H11	1.09663	0.013560	0.132768
H12	0.949959	−0.075341	0.098976
H13	0.593684	0.14326	0.141432
H14	0.45002	0.054351	0.105309
H15	0.740866	−0.106334	0.076006
H16	0.522896	−0.070833	0.072332
H17	1.01306	0.202319	0.160768
H18	0.752492	0.123534	0.320783
H19	0.507735	0.167108	0.594133
H20	0.478754	0.074634	0.721263
H21	0.858078	−0.008219	0.561693
H22	0.657618	−0.012174	0.705706
O1	0.667947	0.249293	0.471869
O2	1.21287	0.088107	0.184463

(34)

Crystal data

Triclinic, P1	α = 59.1°
a = 15.9 Å	β = 68.4°
b = 10.2 Å	γ = 84.5°
c = 10.9 Å	V = 1408.32 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.325292	0.118212	0.531635
C2	0.370464	0.031383	0.630406
C3	0.320779	−0.057535	0.787065
C4	0.225636	−0.064911	0.847492
C5	0.181303	0.022867	0.74618
C6	0.230895	0.114458	0.589457
C7	0.17509	−0.172326	1.016
C8	0.181642	−0.264978	1.27023
C9	0.200831	−0.218144	1.35686
C10	0.173292	−0.319754	1.51905
C11	0.126323	−0.467739	1.58979
C12	0.108417	−0.50982	1.49628
C13	0.134972	−0.41268	1.34103
C14	0.190755	−0.277997	1.6134
C15	0.163314	−0.377868	1.76907
C16	0.11713	−0.524384	1.83868
C17	0.099045	−0.567925	1.75041
C18	0.249306	−0.062725	1.28229
C19	0.34396	−0.039607	1.23301
C20	0.389001	0.108857	1.16387
C21	0.339506	0.230269	1.14528
C22	0.243398	0.212875	1.19377
C23	0.197818	0.064120	1.26363
C24	0.191786	0.337947	1.17516
C25	0.098503	0.317671	1.22356
C26	0.053121	0.170539	1.29293
C27	0.10131	0.046984	1.31255
C28	0.484916	−0.169088	1.20581
C29	0.517441	−0.324272	1.24723
C30	0.489706	−0.434949	1.22682
C31	0.527528	−0.572813	1.26705
C32	0.593793	−0.602476	1.32995
C33	0.623074	−0.493687	1.35049
C34	0.585629	−0.356063	1.30814
Cl1	0.064056	0.026124	0.811528
Cl2	0.408023	−0.404025	1.14559
N1	0.211453	−0.167791	1.11034
N2	0.392474	−0.167036	1.25589
H1	0.622828	−0.710417	1.36181
H2	0.504887	−0.655223	1.24808
H3	0.675282	−0.515749	1.39862
H4	0.608868	−0.268261	1.31994
H5	0.072852	−0.622713	1.54996
H6	0.120023	−0.445428	1.27114
H7	0.095895	−0.602103	1.96185
H8	0.177176	−0.343605	1.83936
H9	0.063327	−0.680322	1.8026
H10	0.225862	−0.165197	1.56081
H11	0.46244	0.122987	1.12674
H12	0.374752	0.343295	1.09207
H13	0.065815	−0.065711	1.36603
H14	−0.020699	0.154917	1.3311
H15	0.227671	0.450566	1.12161
H16	0.059479	0.414297	1.20872
H17	0.352944	−0.266537	1.30641
H18	0.254249	−0.073311	1.06435
H19	0.355678	−0.126179	0.864709
H20	0.444091	0.033513	0.586085
H21	0.194888	0.182615	0.513852
H22	0.363212	0.189221	0.409033
O1	0.110795	−0.262882	1.06115
O2	0.541002	−0.057789	1.14098

(35)

Crystal data

Monoclinic, P21/n	c = 10.5 Å
a = 13.3 Å	β = 71.4°
b = 21.7 Å	V = 2872.22 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.100922	0.027536	0.838104
C2	0.073491	−0.007464	0.743158
C3	0.09086	0.016067	0.615261
C4	0.13589	0.074382	0.579169
C5	0.162236	0.108968	0.676265
C6	0.144747	0.085868	0.805117
C7	0.14845	0.096217	0.439071
C8	0.288656	0.137524	0.237536
C9	0.397579	0.148481	0.185055
C10	0.439864	0.176222	0.055797
C11	0.370179	0.192437	−0.017744
C12	0.26043	0.180078	0.039891
C13	0.219716	0.153515	0.163872
C14	0.549791	0.188936	−0.002455
C15	0.588102	0.216328	−0.12645
C16	0.519018	0.232275	−0.199002
C17	0.412334	0.22039	−0.145452
C18	0.46836	0.131578	0.264849
C19	0.494396	0.176485	0.344283
C20	0.559382	0.162034	0.423941
C21	0.595767	0.102932	0.424181
C22	0.570742	0.055549	0.346611
C23	0.505819	0.070018	0.265583
C24	0.608213	−0.005548	0.347249
C25	0.583006	−0.050766	0.271183
C26	0.519061	−0.036481	0.190781
C27	0.481407	0.022322	0.187807
C28	0.461219	0.287763	0.410287
C29	0.396341	0.340012	0.383393
C30	0.331706	0.376832	0.486891
C31	0.274386	0.425786	0.458864
C32	0.281341	0.438926	0.326974
C33	0.344898	0.402875	0.222764
C34	0.401271	0.353794	0.251462
Cl1	0.213983	0.183237	0.642373
Cl2	0.316294	0.361727	0.654065
N1	0.250216	0.111957	0.365994
N2	0.454213	0.235606	0.339359
H1	0.236613	0.477367	0.306195
H2	0.224206	0.453097	0.541212
H3	0.350903	0.41287	0.119487
H4	0.452399	0.326263	0.169832
H5	0.207347	0.19235	−0.016111
H6	0.135845	0.144021	0.207684
H7	0.550539	0.253774	−0.297003
H8	0.672506	0.225617	−0.169364
H9	0.358301	0.232328	−0.200366
H10	0.603421	0.176402	0.052442
H11	0.578274	0.198232	0.483438
H12	0.645277	0.091734	0.485612
H13	0.432677	0.033110	0.125315
H14	0.499656	−0.072382	0.130425
H15	0.657538	−0.015958	0.409372
H16	0.612193	−0.097474	0.272416
H17	0.404683	0.238254	0.283855
H18	0.305351	0.106478	0.412776
H19	0.068390	−0.010132	0.540583
H20	0.038683	−0.052923	0.768718
H21	0.165104	0.11405	0.878531
H22	0.087583	0.009738	0.938657
O1	0.072670	0.097157	0.397592
O2	0.514127	0.292231	0.485259

(36)

Crystal data

Triclinic, P1	α = 105.3°
a = 10.5 Å	β = 76.4°
b = 11.1 Å	γ = 67.0°
c = 14.0 Å	V = 1341.08 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.701236	0.571754	0.94575
C2	0.714092	0.544463	0.840116
C3	0.586287	0.593605	0.817737
C4	0.443029	0.668442	0.898223
C5	0.433501	0.69567	1.004
C6	0.560941	0.64828	1.02776
C7	0.315934	0.715312	0.860782
C8	0.060072	0.755977	0.89312
C9	0.056038	0.683895	0.797889
C10	−0.081607	0.737547	0.781577
C11	−0.212261	0.858877	0.865543
C12	−0.203285	0.924345	0.963389
C13	−0.070312	0.874726	0.976544
C14	−0.093659	0.6732	0.684539
C15	−0.227139	0.726848	0.671464
C16	−0.355901	0.846534	0.754606
C17	−0.348305	0.910922	0.849682
C18	0.186262	0.546893	0.715499
C19	0.267442	0.541252	0.619581
C20	0.379332	0.4093	0.535739
C21	0.410498	0.284647	0.549642
C22	0.332223	0.284976	0.647204
C23	0.217026	0.417615	0.731327
C24	0.364146	0.156516	0.662437
C25	0.285188	0.157631	0.756235
C26	0.169667	0.288251	0.838757
C27	0.136339	0.414813	0.826631
C28	0.209837	0.698517	0.524696
C29	0.182819	0.84413	0.5299
C30	0.240505	0.866467	0.439169
C31	0.209242	1.00322	0.445585
C32	0.118699	1.12012	0.542701
C33	0.060328	1.10039	0.633768
C34	0.093110	0.963454	0.626863
Cl1	0.263032	0.795762	1.11414
Cl2	0.358414	0.725415	0.315873
N1	0.193976	0.708673	0.912388
N2	0.241414	0.670518	0.608083
H1	0.094383	1.22644	0.546769
H2	0.256778	1.01676	0.374086
H3	−0.010641	1.19105	0.709913
H4	0.045873	0.947968	0.697572
H5	−0.303193	1.01562	1.02755
H6	−0.061664	0.926717	1.05034
H7	−0.460627	0.887559	0.743058
H8	−0.233139	0.676733	0.596009
H9	−0.446627	1.0033	0.914415
H10	0.004540	0.582068	0.619297
H11	0.438302	0.409773	0.461191
H12	0.496645	0.183086	0.485543
H13	0.046150	0.514506	0.8902
H14	0.106156	0.288636	0.912381
H15	0.452482	0.056434	0.59785
H16	0.310621	0.058350	0.766883
H17	0.247716	0.742167	0.666704
H18	0.191657	0.684726	0.977297
H19	0.593492	0.575783	0.73616
H20	0.823164	0.485753	0.77542
H21	0.548817	0.672732	1.11071
H22	0.800049	0.534701	0.964922
O1	0.327289	0.754453	0.786576
O2	0.200268	0.61496	0.453906

(37)

Crystal data

Triclinic, P1	α = 86.0°
a = 10.9 Å	β = 60.6°
b = 14.1 Å	γ = 75.8°
c = 10.9 Å	V = 1419.96 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.62345	0.814006	0.27107
C2	0.68314	0.746557	0.157852
C3	0.592237	0.711682	0.127027
C4	0.441248	0.743003	0.208059
C5	0.383185	0.810727	0.321817
C6	0.473616	0.846369	0.352769
C7	0.348161	0.697996	0.175857
C8	0.336748	0.650684	−0.033692
C9	0.38424	0.665327	−0.175762
C10	0.340445	0.614603	−0.25049
C11	0.249319	0.549385	−0.17884
C12	0.205483	0.536326	−0.034745
C13	0.247263	0.58486	0.037021
C14	0.384193	0.627225	−0.395053
C15	0.339086	0.578366	−0.463946
C16	0.248562	0.514148	−0.392635
C17	0.205055	0.500018	−0.25296
C18	0.475994	0.735656	−0.249306
C19	0.412898	0.830096	−0.26783
C20	0.500255	0.897067	−0.339038
C21	0.647281	0.868983	−0.392383
C22	0.716914	0.773585	−0.378777
C23	0.629874	0.70623	−0.306992
C24	0.869035	0.743413	−0.434
C25	0.933826	0.650253	−0.419297
C26	0.848158	0.583168	−0.348641
C27	0.700247	0.610271	−0.293889
C28	0.185633	0.936888	−0.250212
C29	0.028678	0.937435	−0.191081
C30	−0.081548	1.02378	−0.138083
C31	−0.225182	1.02263	−0.090849
C32	−0.260547	0.935816	−0.097327
C33	−0.152647	0.849534	−0.150215
C34	−0.009637	0.850848	−0.196147
Cl1	0.197224	0.855606	0.424616
Cl2	−0.047016	1.13424	−0.121898
N1	0.383291	0.699779	0.036640
N2	0.262651	0.858352	−0.214448
H1	−0.372925	0.936057	−0.060724
H2	−0.308575	1.09023	−0.048711
H3	−0.179189	0.781544	−0.156372
H4	0.075225	0.783868	−0.24081
H5	0.13645	0.48644	0.019972
H6	0.212038	0.575582	0.147493
H7	0.214015	0.475935	−0.448546
H8	0.373855	0.589056	−0.574591
H9	0.135748	0.450516	−0.19684
H10	0.454556	0.675987	−0.451039
H11	0.447872	0.969839	−0.35099
H12	0.7125	0.921098	−0.446354
H13	0.635213	0.557976	−0.240915
H14	0.899805	0.509255	−0.33812
H15	0.933661	0.795754	−0.488554
H16	1.05062	0.627857	−0.462163
H17	0.206512	0.811479	−0.149828
H18	0.453959	0.740094	−0.024748
H19	0.638387	0.658735	0.038880
H20	0.799959	0.720948	0.093787
H21	0.42565	0.899612	0.440591
H22	0.693133	0.842028	0.296275
O1	0.256851	0.659543	0.265714
O2	0.237416	1.00017	−0.325231

(38)

Crystal data

Triclinic, P1	α = 89.8°
a = 14.0 Å	β = 75.1°
b = 10.3 Å	γ = 63.4°
c = 11.4 Å	V = 1409.76 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.992332	0.505616	0.827358
C2	1.08064	0.508428	0.739565
C3	1.068	0.63943	0.695699
C4	0.967908	0.770614	0.734217
C5	0.880621	0.764689	0.82361
C6	0.892855	0.633812	0.869571
C7	0.973638	0.900915	0.676995
C8	0.859385	1.16393	0.657716
C9	0.753001	1.26939	0.658745
C10	0.73311	1.41598	0.639916
C11	0.821953	1.45317	0.621415
C12	0.927891	1.3427	0.623364
C13	0.947165	1.20207	0.640873
C14	0.626852	1.52738	0.638473
C15	0.610225	1.66723	0.61883
C16	0.698394	1.70352	0.60011
C17	0.801947	1.59834	0.601663
C18	0.660616	1.22974	0.678288
C19	0.640315	1.17815	0.579509
C20	0.553533	1.13784	0.597613
C21	0.487562	1.15147	0.712832
C22	0.503431	1.20508	0.816278
C23	0.590877	1.24449	0.798429
C24	0.435428	1.21986	0.935896
C25	0.452145	1.27262	1.03499
C26	0.538131	1.313	1.01778
C27	0.605424	1.29946	0.902812
C28	0.70805	1.10792	0.353016
C29	0.753	1.16687	0.243568
C30	0.823191	1.07769	0.132995
C31	0.854329	1.13866	0.030343
C32	0.814205	1.29015	0.036140
C33	0.743827	1.38079	0.144695
C34	0.713989	1.31895	0.24718
Cl1	0.752911	0.918258	0.88837
Cl2	0.877983	0.887833	0.120958
N1	0.87614	1.02155	0.678565
N2	0.706089	1.16822	0.461524
H1	0.838461	1.33681	−0.044654
H2	0.910011	1.06663	−0.053492
H3	0.711997	1.49913	0.149777
H4	0.658342	1.3893	0.332031
H5	0.995543	1.37098	0.610081
H6	1.02882	1.11782	0.640011
H7	0.683956	1.81458	0.584936
H8	0.528239	1.75097	0.618306
H9	0.870492	1.62494	0.587685
H10	0.558415	1.50056	0.653969
H11	0.542351	1.09428	0.519
H12	0.421422	1.12029	0.725829
H13	0.671414	1.33061	0.890615
H14	0.550977	1.35516	1.09626
H15	0.369387	1.18865	0.947663
H16	0.399447	1.2837	1.1264
H17	0.75693	1.21484	0.455583
H18	0.805676	1.01108	0.706204
H19	1.13611	0.645302	0.628865
H20	1.15931	0.409353	0.706173
H21	0.823508	0.634498	0.939194
H22	1.00054	0.404335	0.863598
O1	1.06504	0.894847	0.633901
O2	0.668781	1.0252	0.344553

(39)

Crystal data

Monoclinic, P21/c	c = 19.6 Å
a = 11.0 Å	β = 54.6°
b = 15.8 Å	V = 2778.17 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.020989	0.266393	0.663244
C2	0.085613	0.221468	0.588787
C3	0.001120	0.162639	0.580822
C4	−0.149153	0.14794	0.645448
C5	−0.211457	0.193172	0.720112
C6	−0.126882	0.251812	0.728978
C7	−0.224488	0.081106	0.627444
C8	−0.457847	0.051521	0.637867
C9	−0.60201	0.080294	0.671452
C10	−0.697903	0.032575	0.659021
C11	−0.645288	−0.044320	0.612568
C12	−0.498199	−0.071011	0.579991
C13	−0.405966	−0.025136	0.591705
C14	−0.845816	0.058961	0.691867
C15	−0.935976	0.011654	0.679216
C16	−0.88357	−0.064343	0.633217
C17	−0.741086	−0.091519	0.600665
C18	−0.656997	0.15935	0.721993
C19	−0.721617	0.157444	0.807478
C20	−0.771281	0.232477	0.855898
C21	−0.756329	0.308424	0.8186
C22	−0.692292	0.314175	0.731902
C23	−0.642588	0.238732	0.683157
C24	−0.676203	0.392381	0.692525
C25	−0.6136	0.396458	0.608289
C26	−0.56435	0.321941	0.559901
C27	−0.578462	0.24508	0.596277
C28	−0.739723	0.064501	0.915151
C29	−0.768281	−0.026391	0.942183
C30	−0.858185	−0.050643	1.02653
C31	−0.87822	−0.135544	1.04889
C32	−0.807616	−0.197466	0.987469
C33	−0.717342	−0.174785	0.903369
C34	−0.698854	−0.090042	0.881434
Cl1	−0.393787	0.176198	0.806804
Cl2	−0.95392	0.022714	1.10668
N1	−0.36489	0.099909	0.649875
N2	−0.738594	0.079185	0.845732
H1	−0.823437	−0.263441	1.0057
H2	−0.949761	−0.152327	1.11469
H3	−0.660798	−0.222651	0.854979
H4	−0.624666	−0.072563	0.815745
H5	−0.457841	−0.129586	0.544651
H6	−0.293837	−0.045897	0.566895
H7	−0.956108	−0.101027	0.623685
H8	−1.04868	0.033010	0.704724
H9	−0.699392	−0.149909	0.565082
H10	−0.886587	0.117597	0.7269
H11	−0.818445	0.228352	0.921966
H12	−0.794362	0.365782	0.855911
H13	−0.54072	0.187947	0.558767
H14	−0.515009	0.325421	0.493291
H15	−0.714579	0.449319	0.730491
H16	−0.601863	0.456801	0.578753
H17	−0.75464	0.029159	0.819865
H18	−0.411762	0.154047	0.682198
H19	0.050046	0.125568	0.524059
H20	0.201535	0.231902	0.537335
H21	−0.178128	0.285063	0.787977
H22	0.085770	0.312399	0.670707
O1	−0.156944	0.016106	0.59241
O2	−0.716306	0.118557	0.950471

(40)

Crystal data

Orthorhombic, P212121	c = 10.5 Å
a = 23.1 Å	V = 2815.9 Å^3
b = 11.6 Å

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.452427	0.320088	0.819924
C2	0.43504	0.244625	0.915267
C3	0.474635	0.166445	0.965022
C4	0.531775	0.160921	0.921063
C5	0.548339	0.237918	0.824947
C6	0.509011	0.317046	0.775215
C7	0.573316	0.073185	0.973875
C8	0.61232	0.015401	1.18561
C9	0.609066	0.040367	1.31472
C10	0.648866	−0.012732	1.40038
C11	0.692435	−0.088359	1.35218
C12	0.694458	−0.109444	1.22002
C13	0.655777	−0.059868	1.13805
C14	0.646858	0.007508	1.5331
C15	0.68614	−0.043891	1.61308
C16	0.7294	−0.118196	1.56507
C17	0.732264	−0.139914	1.43716
C18	0.562904	0.118655	1.3639
C19	0.573289	0.235964	1.38408
C20	0.528816	0.308468	1.43272
C21	0.475417	0.263573	1.45975
C22	0.462641	0.145274	1.44095
C23	0.507136	0.071820	1.39289
C24	0.407467	0.098354	1.46876
C25	0.396246	−0.016910	1.45009
C26	0.4402	−0.089989	1.40293
C27	0.494191	−0.047049	1.37509
C28	0.648423	0.390265	1.36867
C29	0.707991	0.413296	1.31567
C30	0.756454	0.340478	1.32075
C31	0.808937	0.373284	1.26641
C32	0.813816	0.47921	1.20542
C33	0.766476	0.553509	1.20052
C34	0.714599	0.520562	1.2559
Cl1	0.618682	0.242319	0.76726
Cl2	0.755533	0.208507	1.40048
N1	0.572388	0.068374	1.10427
N2	0.628145	0.279864	1.35429
H1	0.854828	0.503697	1.16281
H2	0.845715	0.315325	1.27325
H3	0.769991	0.636913	1.15403
H4	0.677313	0.577641	1.25512
H5	0.7277	−0.166851	1.18313
H6	0.65734	−0.076507	1.03717
H7	0.76019	−0.158051	1.62949
H8	0.683902	−0.027202	1.71438
H9	0.76527	−0.197142	1.39892
H10	0.613718	0.064473	1.57084
H11	0.538419	0.398844	1.44789
H12	0.441786	0.319982	1.49681
H13	0.527814	−0.104079	1.33964
H14	0.431285	−0.181266	1.38882
H15	0.374119	0.155636	1.50547
H16	0.353799	−0.052139	1.47176
H17	0.655945	0.220633	1.31846
H18	0.54528	0.124134	1.14836
H19	0.460832	0.106114	1.03813
H20	0.390912	0.246127	0.950619
H21	0.523313	0.376163	0.701756
H22	0.422078	0.381865	0.780033
O1	0.604067	0.014229	0.906086
O2	0.620669	0.469906	1.41436

(41)

Crystal data

Triclinic, P1	α = 72.4°
a = 11.7 Å	β = 69.6°
b = 13.3 Å	γ = 98.8°
c = 10.6 Å	V = 1413.92 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.784525	0.967329	0.599652
C2	0.835398	0.882376	0.578968
C3	0.912862	0.894005	0.439558
C4	0.943736	0.990565	0.318419
C5	0.890302	1.07441	0.341255
C6	0.8111	1.06275	0.480931
C7	1.02856	0.987345	0.176334
C8	1.2172	1.1027	−0.056643
C9	1.2964	1.21029	−0.140545
C10	1.39632	1.23372	−0.278786
C11	1.41478	1.14672	−0.329321
C12	1.33345	1.03867	−0.239043
C13	1.23775	1.01621	−0.10647
C14	1.4791	1.34186	−0.369157
C15	1.57395	1.36228	−0.502171
C16	1.59153	1.27609	−0.552079
C17	1.51343	1.17057	−0.466917
C18	1.27814	1.30086	−0.086715
C19	1.20083	1.36415	−0.120182
C20	1.1849	1.45084	−0.069131
C21	1.24156	1.47006	0.017481
C22	1.31836	1.40597	0.057781
C23	1.33741	1.32074	0.004102
C24	1.3767	1.42445	0.148354
C25	1.4515	1.36144	0.184942
C26	1.47101	1.27726	0.131567
C27	1.41573	1.25743	0.043303
C28	1.03236	1.36834	−0.207082
C29	0.994807	1.35272	−0.322766
C30	0.867846	1.3081	−0.293828
C31	0.834186	1.30446	−0.406199
C32	0.92594	1.34702	−0.548933
C33	1.05205	1.39254	−0.579954
C34	1.08534	1.39505	−0.467236
Cl1	0.913863	1.19456	0.198114
Cl2	0.748937	1.25027	−0.118367
N1	1.12178	1.08301	0.079040
N2	1.14504	1.34747	−0.212382
H1	0.898195	1.34429	−0.635644
H2	0.735683	1.26797	−0.380582
H3	1.1241	1.42642	−0.691158
H4	1.18335	1.43191	−0.490622
H5	1.34782	0.971919	−0.276412
H6	1.17531	0.933589	−0.038255
H7	1.66697	1.2935	−0.657436
H8	1.63636	1.44558	−0.569523
H9	1.52617	1.10336	−0.503823
H10	1.46666	1.40846	−0.331131
H11	1.12555	1.49993	−0.097651
H12	1.22788	1.53621	0.056295
H13	1.43156	1.19277	0.002273
H14	1.53051	1.22776	0.160385
H15	1.36102	1.48971	0.188448
H16	1.49582	1.37623	0.254566
H17	1.17493	1.29699	−0.26338
H18	1.12078	1.15023	0.105298
H19	0.951446	0.828158	0.419951
H20	0.813997	0.807089	0.671077
H21	0.770174	1.12875	0.494826
H22	0.723079	0.95931	0.708044
O1	1.01559	0.900528	0.157864
O2	0.969219	1.40276	−0.120532

(42)

Crystal data

Triclinic, P1	α = 75.1°
a = 9.9 Å	β = 103.3°
b = 14.0 Å	γ = 98.9°
c = 11.0 Å	V = 1436.81 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.320512	0.788317	0.534831
C2	0.346179	0.888848	0.478827
C3	0.435689	0.918145	0.393545
C4	0.499986	0.849255	0.359951
C5	0.474057	0.748636	0.418812
C6	0.385064	0.718436	0.505463
C7	0.598686	0.891	0.269721
C8	0.646943	0.870977	0.065625
C9	0.61858	0.807037	−0.017429
C10	0.685661	0.829055	−0.123904
C11	0.782775	0.915484	−0.142976
C12	0.809568	0.977186	−0.054889
C13	0.743973	0.9566	0.046542
C14	0.659715	0.767168	−0.212203
C15	0.726244	0.790019	−0.313655
C16	0.822185	0.87556	−0.332321
C17	0.849597	0.936795	−0.248469
C18	0.521786	0.714776	0.008193
C19	0.570793	0.628229	0.090102
C20	0.478718	0.54052	0.116327
C21	0.340504	0.540402	0.062187
C22	0.285132	0.626541	−0.020965
C23	0.377171	0.714653	−0.048294
C24	0.142188	0.627597	−0.077249
C25	0.091241	0.712228	−0.157786
C26	0.182026	0.799571	−0.185179
C27	0.321302	0.800872	−0.132008
C28	0.773222	0.56431	0.249494
C29	0.928002	0.558541	0.27493
C30	1.03261	0.628981	0.229952
C31	1.171	0.609243	0.262245
C32	1.20795	0.518237	0.339776
C33	1.10642	0.44722	0.386407
C34	0.969209	0.467932	0.354421
Cl1	0.555404	0.656767	0.392042
Cl2	1.0001	0.747376	0.135815
N1	0.575099	0.849466	0.166152
N2	0.713823	0.627966	0.141146
H1	1.31608	0.503507	0.363992
H2	1.24887	0.666092	0.226443
H3	1.13404	0.375999	0.447735
H4	0.888126	0.414567	0.390723
H5	0.883998	1.04277	−0.068905
H6	0.765082	1.00363	0.114039
H7	0.873967	0.892641	−0.412973
H8	0.704737	0.74185	−0.380343
H9	0.923296	1.00287	−0.261775
H10	0.585702	0.701443	−0.1986
H11	0.519374	0.474666	0.181293
H12	0.271069	0.472839	0.083097
H13	0.390706	0.868197	−0.15379
H14	0.141374	0.866344	−0.249055
H15	0.073385	0.559814	−0.055384
H16	−0.018606	0.712207	−0.200536
H17	0.776502	0.680278	0.092438
H18	0.500704	0.791303	0.16457
H19	0.459207	0.996428	0.351168
H20	0.297343	0.944268	0.501978
H21	0.368435	0.639958	0.549965
H22	0.251234	0.764055	0.602313
O1	0.687874	0.958755	0.289425
O2	0.70545	0.508323	0.323753

(43)

Crystal data

Monoclinic, P21/n	c = 11.6 Å
a = 18.2 Å	β = 74.2°
b = 13.7 Å	V = 2804.93 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.513502	0.624764	0.456321
C2	0.591451	0.617052	0.443246
C3	0.636872	0.565478	0.347634
C4	0.606029	0.520191	0.263709
C5	0.527629	0.529336	0.278104
C6	0.481583	0.581606	0.373256
C7	0.66059	0.46545	0.164673
C8	0.680779	0.304164	0.065724
C9	0.669625	0.205157	0.089292
C10	0.708861	0.136331	0.001731
C11	0.756847	0.170215	−0.109372
C12	0.76492	0.271728	−0.129616
C13	0.728339	0.337502	−0.045152
C14	0.702622	0.034485	0.021912
C15	0.741177	−0.029876	−0.063760
C16	0.787952	0.003841	−0.174024
C17	0.795576	0.101992	−0.195913
C18	0.619928	0.171986	0.206868
C19	0.64249	0.181887	0.311806
C20	0.593023	0.15171	0.423065
C21	0.523897	0.110758	0.428156
C22	0.498846	0.097650	0.324471
C23	0.547346	0.129264	0.212848
C24	0.427265	0.055550	0.329034
C25	0.403578	0.045401	0.227339
C26	0.450864	0.077846	0.116785
C27	0.520648	0.118824	0.10961
C28	0.74734	0.232794	0.397684
C29	0.83203	0.250423	0.367133
C30	0.875358	0.313708	0.2808
C31	0.953022	0.326453	0.267512
C32	0.988514	0.276239	0.34099
C33	0.946167	0.214527	0.429346
C34	0.868773	0.203215	0.44273
Cl1	0.484344	0.478849	0.175485
Cl2	0.834086	0.382148	0.18911
N1	0.640962	0.37114	0.15092
N2	0.715802	0.217028	0.30502
H1	1.0491	0.286322	0.329819
H2	0.984723	0.376504	0.200006
H3	0.973256	0.176018	0.488256
H4	0.834301	0.157533	0.512978
H5	0.801236	0.297423	−0.214488
H6	0.735563	0.414942	−0.060418
H7	0.817935	−0.047886	−0.241012
H8	0.735624	−0.107552	−0.046371
H9	0.831753	0.129031	−0.2802
H10	0.666824	0.007778	0.106428
H11	0.611478	0.161892	0.502961
H12	0.487103	0.087722	0.513974
H13	0.556266	0.143819	0.024111
H14	0.431798	0.070570	0.036494
H15	0.391314	0.031674	0.415107
H16	0.348581	0.013028	0.231668
H17	0.75056	0.224683	0.221314
H18	0.595111	0.34442	0.212647
H19	0.697885	0.559386	0.335262
H20	0.616774	0.650909	0.507577
H21	0.421158	0.588145	0.381095
H22	0.477295	0.665002	0.530697
O1	0.719183	0.504229	0.106247
O2	0.711633	0.230529	0.503129

(44)

Crystal data

Monoclinic, P21/c	c = 20.0 Å
a = 15.2 Å	β = 59.0°
b = 10.8 Å	V = 2805.75 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.296434	0.590837	0.7281
C2	0.255256	0.506852	0.698714
C3	0.1816	0.422052	0.748644
C4	0.148561	0.418663	0.828031
C5	0.191202	0.503753	0.856366
C6	0.26418	0.589786	0.806956
C7	0.073826	0.320621	0.879842
C8	−0.108501	0.260868	0.928467
C9	−0.191959	0.286376	0.919819
C10	−0.285926	0.220433	0.966778
C11	−0.29435	0.134656	1.02428
C12	−0.207973	0.115032	1.03193
C13	−0.11698	0.17518	0.985394
C14	−0.371966	0.235544	0.957685
C15	−0.461297	0.170965	1.00376
C16	−0.469847	0.087945	1.06142
C17	−0.387709	0.070225	1.0711
C18	−0.181703	0.375484	0.859099
C19	−0.229461	0.491408	0.87934
C20	−0.219805	0.574342	0.820624
C21	−0.161283	0.542681	0.743632
C22	−0.109982	0.427063	0.719923
C23	−0.121482	0.341628	0.778432
C24	−0.048846	0.394142	0.640256
C25	−0.000758	0.280754	0.618453
C26	−0.013036	0.195118	0.67611
C27	−0.072001	0.224344	0.753917
C28	−0.308684	0.644462	0.986897
C29	−0.361903	0.658356	1.07402
C30	−0.451441	0.598646	1.13027
C31	−0.49581	0.625755	1.20925
C32	−0.450678	0.713367	1.2332
C33	−0.362128	0.775139	1.17823
C34	−0.319484	0.748545	1.0997
Cl1	0.151771	0.507985	0.954659
Cl2	−0.512667	0.48896	1.10406
N1	−0.017472	0.326514	0.881634
N2	−0.287427	0.525656	0.9581
H1	−0.485364	0.733759	1.29487
H2	−0.565671	0.57814	1.25113
H3	−0.326886	0.844455	1.19646
H4	−0.252048	0.797936	1.0558
H5	−0.214361	0.049839	1.07573
H6	−0.050563	0.159143	0.990615
H7	−0.541057	0.037876	1.09756
H8	−0.525914	0.183636	0.995468
H9	−0.392815	0.005722	1.11479
H10	−0.366161	0.298336	0.913116
H11	−0.257584	0.663601	0.838023
H12	−0.153938	0.607467	0.699352
H13	−0.081865	0.157118	0.797688
H14	0.023870	0.104723	0.658848
H15	−0.041000	0.460698	0.596621
H16	0.045947	0.256302	0.557202
H17	−0.304903	0.456352	0.997138
H18	−0.022130	0.392897	0.847786
H19	0.149432	0.355804	0.725923
H20	0.280162	0.507158	0.637217
H21	0.295047	0.655439	0.830761
H22	0.353809	0.657837	0.689815
O1	0.094871	0.245723	0.915061
O2	−0.283388	0.737807	0.946477

(45)

Crystal data

Monoclinic, P21/c	c = 14.9 Å
a = 10.6 Å	β = 65.5°
b = 19.9 Å	V = 2857.69 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.183223	0.988423	0.379392
C2	0.082996	0.954981	0.358444
C3	0.011182	0.901712	0.417165
C4	0.036169	0.880294	0.497846
C5	0.138958	0.914051	0.516602
C6	0.212164	0.967538	0.457809
C7	−0.051122	0.822065	0.554228
C8	−0.161984	0.773662	0.722888
C9	−0.228346	0.790409	0.822345
C10	−0.292279	0.738963	0.893576
C11	−0.286959	0.67102	0.862066
C12	−0.217221	0.656568	0.760222
C13	−0.156368	0.705909	0.692027
C14	−0.362174	0.753225	0.995811
C15	−0.423219	0.702843	1.06274
C16	−0.417626	0.635684	1.03136
C17	−0.350855	0.6203	0.932948
C18	−0.227318	0.861118	0.854697
C19	−0.127369	0.882856	0.88639
C20	−0.125752	0.950497	0.91583
C21	−0.22292	0.994827	0.913138
C22	−0.327332	0.975139	0.882358
C23	−0.329742	0.907275	0.852936
C24	−0.428727	1.02072	0.880223
C25	−0.529279	1.00041	0.850325
C26	−0.532105	0.933259	0.821266
C27	−0.435081	0.887875	0.822479
C28	0.090911	0.847744	0.900755
C29	0.185928	0.788017	0.87651
C30	0.261604	0.771146	0.931458
C31	0.356247	0.718369	0.902702
C32	0.378203	0.682014	0.817917
C33	0.304788	0.698021	0.762046
C34	0.209634	0.750431	0.791653
Cl1	0.186697	0.890066	0.610964
Cl2	0.236566	0.812775	1.03975
N1	−0.098366	0.824692	0.65457
N2	−0.030093	0.836433	0.889678
H1	0.452872	0.641169	0.795891
H2	0.411926	0.706109	0.947469
H3	0.321675	0.670178	0.69547
H4	0.154036	0.763651	0.747007
H5	−0.212343	0.604842	0.735976
H6	−0.105818	0.694558	0.614159
H7	−0.466268	0.596401	1.08517
H8	−0.476539	0.714801	1.14063
H9	−0.345934	0.568789	0.907813
H10	−0.367482	0.804831	1.02033
H11	−0.046425	0.965582	0.939812
H12	−0.220834	1.04652	0.935667
H13	−0.438383	0.836264	0.800332
H14	−0.611987	0.917313	0.797846
H15	−0.425396	1.07228	0.902875
H16	−0.606685	1.03575	0.849018
H17	−0.049242	0.788225	0.878161
H18	−0.083919	0.868562	0.683091
H19	−0.066334	0.874355	0.401713
H20	0.060574	0.970553	0.296765
H21	0.29183	0.992132	0.474022
H22	0.240319	1.03035	0.334269
O1	−0.077018	0.776551	0.509567
O2	0.124245	0.901537	0.923151

(46)

Crystal data

Monoclinic, P21/n	c = 15.9 Å
a = 11.4 Å	β = 87.2°
b = 15.3 Å	V = 2766.4 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.326285	0.450539	0.49309
C2	0.212191	0.465307	0.525284
C3	0.120537	0.416646	0.495534
C4	0.138344	0.35172	0.433846
C5	0.254029	0.339106	0.401632
C6	0.346826	0.387845	0.430979
C7	0.025374	0.306479	0.412624
C8	−0.058814	0.169707	0.357886
C9	−0.038035	0.104489	0.297627
C10	−0.127873	0.042332	0.282367
C11	−0.238331	0.048066	0.328614
C12	−0.255403	0.115738	0.388694
C13	−0.16915	0.175139	0.403383
C14	−0.111775	−0.024914	0.221391
C15	−0.200199	−0.083352	0.207586
C16	−0.309109	−0.077825	0.25374
C17	−0.327521	−0.013284	0.312933
C18	0.076768	0.101214	0.248074
C19	0.091652	0.155452	0.177622
C20	0.197703	0.154029	0.127069
C21	0.286296	0.098595	0.147561
C22	0.275098	0.042132	0.218184
C23	0.168355	0.043345	0.269376
C24	0.366294	−0.015469	0.239226
C25	0.353183	−0.069900	0.30778
C26	0.247667	−0.068779	0.358394
C27	0.157571	−0.013563	0.33992
C28	−0.031435	0.241162	0.080906
C29	−0.156768	0.272621	0.081707
C30	−0.193243	0.342793	0.032647
C31	−0.310759	0.367953	0.033948
C32	−0.394507	0.323049	0.083578
C33	−0.360802	0.252814	0.132265
C34	−0.243382	0.228475	0.131114
Cl1	0.291763	0.264961	0.321177
Cl2	−0.094439	0.40438	−0.029145
N1	0.033381	0.227386	0.372981
N2	−0.002643	0.208939	0.158316
H1	−0.485922	0.343129	0.083843
H2	−0.335348	0.423173	−0.004102
H3	−0.425346	0.216592	0.170771
H4	−0.219319	0.171413	0.167014
H5	−0.339471	0.120274	0.423947
H6	−0.183623	0.22727	0.448585
H7	−0.37805	−0.124606	0.242199
H8	−0.186172	−0.134365	0.16065
H9	−0.411057	−0.008253	0.348824
H10	−0.028202	−0.029578	0.185741
H11	0.20568	0.196128	0.072308
H12	0.3676	0.097460	0.108688
H13	0.076632	−0.013015	0.379074
H14	0.237775	−0.112024	0.412539
H15	0.447131	−0.015774	0.199809
H16	0.423662	−0.113869	0.323268
H17	−0.065790	0.213132	0.20513
H18	0.113998	0.207746	0.350895
H19	0.030592	0.427224	0.518867
H20	0.194642	0.514602	0.573387
H21	0.434848	0.37622	0.404145
H22	0.399403	0.487948	0.515536
O1	−0.068620	0.340104	0.434438
O2	0.035373	0.242771	0.018670

(47)

Crystal data

Monoclinic, P21/n	c = 10.7 Å
a = 13.8 Å	β = 87.2°
b = 18.7 Å	V = 2763.92 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.144355	0.024878	0.071744
C2	0.136576	0.002970	−0.051568
C3	0.098987	−0.064037	−0.076115
C4	0.067407	−0.110197	0.020313
C5	0.076302	−0.087179	0.14359
C6	0.114875	−0.020242	0.169263
C7	0.030000	−0.181707	−0.019492
C8	−0.096226	−0.272282	0.030859
C9	−0.195919	−0.280753	0.049627
C10	−0.237116	−0.350815	0.046057
C11	−0.175943	−0.410808	0.018566
C12	−0.075037	−0.399249	−0.001766
C13	−0.035621	−0.332369	0.004712
C14	−0.337846	−0.362891	0.068801
C15	−0.37569	−0.430742	0.063705
C16	−0.3151	−0.489935	0.035761
C17	−0.217236	−0.479946	0.013730
C18	−0.25823	−0.217621	0.081668
C19	−0.26427	−0.188477	0.20141
C20	−0.321448	−0.1266	0.227722
C21	−0.372032	−0.095459	0.135529
C22	−0.368517	−0.12281	0.012388
C23	−0.310274	−0.18431	−0.014860
C24	−0.420051	−0.090488	−0.083735
C25	−0.414482	−0.117508	−0.202971
C26	−0.356563	−0.178183	−0.230554
C27	−0.305793	−0.210734	−0.139201
C28	−0.221453	−0.209615	0.421779
C29	−0.176753	−0.266854	0.498883
C30	−0.127248	−0.251329	0.606786
C31	−0.094225	−0.3061	0.681692
C32	−0.111584	−0.377081	0.651335
C33	−0.161473	−0.393637	0.545481
C34	−0.193562	−0.338755	0.470496
Cl1	0.044153	−0.141431	0.271328
Cl2	−0.099939	−0.164269	0.648259
N1	−0.054476	−0.204286	0.040051
N2	−0.212549	−0.221649	0.295083
H1	−0.085922	−0.419307	0.71093
H2	−0.054824	−0.292496	0.763546
H3	−0.175946	−0.448877	0.521583
H4	−0.234603	−0.35172	0.389458
H5	−0.028218	−0.444943	−0.021916
H6	0.041439	−0.324091	−0.011869
H7	−0.346035	−0.543224	0.031814
H8	−0.453038	−0.438874	0.081165
H9	−0.169762	−0.525134	−0.007659
H10	−0.384868	−0.317507	0.089768
H11	−0.323947	−0.105375	0.321631
H12	−0.41571	−0.048273	0.156887
H13	−0.2613	−0.257261	−0.161534
H14	−0.351986	−0.199324	−0.325076
H15	−0.464097	−0.043650	−0.061081
H16	−0.454259	−0.092353	−0.276123
H17	−0.174852	−0.265655	0.267122
H18	−0.091938	−0.167827	0.092582
H19	0.093914	−0.082915	−0.171375
H20	0.159991	0.037856	−0.128161
H21	0.12181	−0.004332	0.265754
H22	0.173991	0.077071	0.092579
O1	0.073823	−0.215443	−0.101708
O2	−0.263725	−0.158946	0.470549

(48)

Crystal data

Monoclinic, P21/n	c = 13.8 Å
a = 10.7 Å	β = 87.2°
b = 18.7 Å	V = 2764.04 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.571996	0.975142	0.14431
C2	0.448649	0.996975	0.136479
C3	0.423989	1.06398	0.098945
C4	0.520354	1.11021	0.067473
C5	0.643662	1.08726	0.076409
C6	0.669448	1.02033	0.114935
C7	0.480456	1.18169	0.030067
C8	0.530625	1.27224	−0.096243
C9	0.549479	1.28071	−0.195929
C10	0.546017	1.35077	−0.237121
C11	0.518576	1.41077	−0.175951
C12	0.498165	1.39921	−0.075053
C13	0.504522	1.33232	−0.035637
C14	0.568837	1.36285	−0.337842
C15	0.563866	1.4307	−0.375682
C16	0.535973	1.48989	−0.315096
C17	0.513863	1.47991	−0.217241
C18	0.581481	1.21758	−0.258231
C19	0.701234	1.18846	−0.264253
C20	0.727525	1.12657	−0.321401
C21	0.635309	1.0954	−0.371955
C22	0.512158	1.12273	−0.368445
C23	0.484925	1.18425	−0.310241
C24	0.416011	1.09038	−0.419948
C25	0.296771	1.11739	−0.414386
C26	0.269209	1.17808	−0.356507
C27	0.360583	1.21066	−0.305769
C28	0.921631	1.20961	−0.221505
C29	0.998714	1.26686	−0.176776
C30	1.10661	1.25133	−0.127235
C31	1.1815	1.3061	−0.094161
C32	1.15113	1.37707	−0.11151
C33	1.04529	1.39363	−0.161443
C34	0.970329	1.33876	−0.193582
Cl1	0.771272	1.14162	0.044348
Cl2	1.14811	1.16428	−0.099932
N1	0.53974	1.20423	−0.054518
N2	0.794934	1.22164	−0.212552
H1	1.21071	1.41929	−0.085808
H2	1.26334	1.29249	−0.054729
H3	1.02139	1.44887	−0.175911
H4	0.889303	1.35172	−0.234656
H5	0.478049	1.4449	−0.028238
H6	0.487876	1.32404	0.041415
H7	0.532124	1.54318	−0.34603
H8	0.581384	1.43883	−0.453024
H9	0.49251	1.52509	−0.169772
H10	0.589765	1.31746	−0.384858
H11	0.821435	1.10535	−0.323896
H12	0.656656	1.0482	−0.415606
H13	0.338269	1.2572	−0.261309
H14	0.174685	1.19922	−0.351939
H15	0.438648	1.04354	−0.463966
H16	0.223601	1.09222	−0.454139
H17	0.767008	1.26567	−0.174904
H18	0.592314	1.16778	−0.091931
H19	0.328697	1.0828	0.093828
H20	0.37212	0.96203	0.159812
H21	0.765962	1.00447	0.121908
H22	0.592912	0.922948	0.173905
O1	0.39839	1.21545	0.074006
O2	0.970377	1.1589	−0.263666

(49)

Crystal data

Triclinic, P1	α = 64.8°
a = 11.5 Å	β = 69.5°
b = 11.2 Å	γ = 61.1°
c = 14.0 Å	V = 1409.21 Å^3

Data collection

h = →	l = →
k = →

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

	x	y	z	Biso*/Beq
C1	0.369106	0.454919	0.139249
C2	0.306738	0.386426	0.123711
C3	0.38507	0.264236	0.092373
C4	0.526031	0.208514	0.075068
C5	0.586618	0.27882	0.091402
C6	0.508976	0.400792	0.123808
C7	0.602653	0.074634	0.042420
C8	0.793967	−0.021766	−0.094276
C9	0.856412	0.014564	−0.201048
C10	0.966017	−0.095712	−0.242592
C11	1.00863	−0.240683	−0.174543
C12	0.941779	−0.271523	−0.066302
C13	0.838005	−0.166042	−0.026372
C14	1.03461	−0.065762	−0.350647
C15	1.13876	−0.173725	−0.388873
C16	1.18026	−0.317102	−0.321378
C17	1.1162	−0.349422	−0.216294
C18	0.816158	0.166159	−0.272194
C19	0.714517	0.22682	−0.331176
C20	0.679788	0.370077	−0.40122
C21	0.747223	0.44903	−0.412532
C22	0.851924	0.39224	−0.35546
C23	0.886964	0.248723	−0.284744
C24	0.922082	0.473276	−0.366585
C25	1.02341	0.415533	−0.310224
C26	1.0585	0.273514	−0.240164
C27	0.99229	0.192169	−0.227639
C28	0.548198	0.180348	−0.370882
C29	0.516333	0.060497	−0.36284
C30	0.607606	−0.077078	−0.367721
C31	0.562912	−0.1735	−0.366053
C32	0.426717	−0.133755	−0.360038
C33	0.334691	0.003526	−0.357522
C34	0.380117	0.099159	−0.36024
Cl1	0.761429	0.214227	0.075642
Cl2	0.781014	−0.135009	−0.380236
N1	0.693275	0.08759	−0.051859
N2	0.64836	0.1433	−0.319963
H1	0.393087	−0.209967