# Pitfalls of a structure determination: The structure of closo-9-[4-(dibenzylamino)phenyl]-1,2-dicarbadodecaborane(12)

Max Milewski, Anne-Marie Caminade, Evamarie Hey-Hawkins, Peter

Lönnecke

► To cite this version:

Max Milewski, Anne-Marie Caminade, Evamarie Hey-Hawkins, Peter Lönnecke. Pitfalls of a structure determination: The structure of closo-9-[4-(dibenzylamino)phenyl]-1,2-dicarbadodecaborane(12). Graciela Diaz de Delgado; Sean Parkin. Modern approaches and tools for teaching crystallography, Art. 6 (Issu de Acta Crystallographica 2022, E78 pp. 1145-1150), IUCr, 2023, 10.1107/S205698902201043X. hal-04195359

HAL Id: hal-04195359

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Submitted on 4 Sep 2023

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Distributed under a Creative Commons CC BY 4.0 - Attribution - International License
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Acta Cryst.

E

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN 2056-9890

Received 4 October 2022

Accepted 30 October 2022

Edited by V. Jancik, Universidad Nacional
Autónoma de México, México

**Keywords:** pitfalls; structure determination; pseudo translation symmetry (PTS); disorder; crystal structure.

CCDC reference: 2216569

**Supporting information:** this article has
supporting information at journals.iucr.org/e

# Pitfalls of a structure determination: The structure of *closo*-9-[4-(dibenzylamino)phenyl]-1,2-dicarbododecaborane(12)

Max Milewski,ª,ᵇ Anne-Marie Caminade,ᵇ Evamarie Hey-Hawkinsª and Peter Lönneckeª*

ªFaculty of Chemistry and Mineralogy, Institute of Inorganic Chemistry, Leipzig University, Johannisallee 29, 04103 Leipzig, Germany, and ᵇCentre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie de Coordination, 205 Route de Narbonne, 31077 Toulouse Cedex 4, France. *Correspondence e-mail: peter.loennecke@uni-leipzig.de

Automated X-ray data recording and data reduction strategies are straightforward and powerful these days, as well as semi-automated routines to solve standard structures without, or at least with only little manual intervention and within a relatively short time. The structure determination of the amino-carborane *closo*-9-[4-(dibenzylamino)phenyl]-1,2-dicarbododecaborane(12), C₂₂H₂₉B₁₀N, is an example that automated routines still always have to be revised and that it may be necessary to be aware of possible problems of a structure determination.

## 1. Chemical context

Derivatives of *closo*-dicarbododecaboranes (carboranes) have been the focus of interest of many research groups over the past few years as building blocks for medicinal chemistry, supramolecular assemblies and ligands in metal complexes (selected references: Stockmann, 2019; Andrews, 1999 and Grimes, 2016). In particular, the readily accessible 1,2-disubstituted *closo*-dicarbododecaboranes (*ortho*-carboranes) are a class of versatile compounds with attractive properties such as a flexible C—C bond. Unlike the C—H groups, the B—H units are much less polar and, depending on their position within the cluster, they exhibit different electronic properties, requiring alternative methods for regioselective substitution. Following the procedures of Zakharkin and co-workers (Zakharkin, 1982), *closo*-9-[4-(dibenzylamino)phenyl]-1,2-dicarbododecaborane(12) was prepared (see Scheme below). After removal of the benzylic protecting groups, the resulting aniline derivative is a suitable functionalized building block for various modifications.

<figure><img src="image_3.png" /></figure>

<figure><img src="image_4.png" /></figure>

<figure><img src="image_5.png" /></figure>

OPEN ACCESS

Published under a CC BY 4.0 licence
<table><caption>**Table 1**
Initial unit cell (Å, °, Å³) derived after the automated data reduction with *CrysAlis PRO* (Rigaku OD, 2020).</caption><thead><tr><th></th><th>Standard cell</th><th></th><th>Non-standard cell<sup>a</sup></th></tr></thead><tbody><tr><td>a<sub>1</sub></td><td>6.5043 (1)</td><td>a<sub>2</sub></td><td>6.5043 (1)</td></tr><tr><td>b<sub>1</sub></td><td>27.1414 (5)</td><td>b<sub>2</sub></td><td>27.1414 (5)</td></tr><tr><td>c<sub>1</sub></td><td>13.2456 (3)</td><td>c<sub>2</sub></td><td>13.9094 (3)</td></tr><tr><td>β<sub>1</sub></td><td>98.101 (2)</td><td>β<sub>2</sub></td><td>109.477 (2)</td></tr><tr><td>V</td><td>2314.99 (8)</td><td>V</td><td>2314.99 (8)</td></tr></tbody></table>

Note (a): Unit-cell transformation matrix by rows: 1 0 0 0 1 0 1 0 1.

## 2. Structural commentary

To quote Anthony Linden (Linden, 2020), 'With a nice graphical user interface (GUI), there is great temptation to click quickly through all the steps of, for example, a structure refinement and the task is complete within minutes, but is the result correct? Is it the best possible result? How can one be sure? Nothing is foolproof (yet!) and users should not rely 100% on automated tools.'

The structure determination of closo-dicarbadodecaborane derivatives based on a 12-vertex icosahedron is frequently hindered, if not prevented, by rotational disorder, especially of the CH and BH vertices. This is a consequence of the approximately spherical shape of a carborane unit and, of course, its relatively weak intermolecular interactions. Up to now, the structures of the pure ortho-, meta- and para-closo-dicarbadodecaboranes are still unknown. Only co-crystallized solvent associates have been published and these lead to precisely defined non-disordered cluster arrangements (Fox & Hughes, 2004). Considering these facts, a carborane structure may easily be associated with a disorder of the carborane unit.

<figure><img src="image_6.png" /><figcaption>**Figure 1**
Reconstructed (hk2)-layer.</figcaption></figure>

<table><caption>**Table 2**
Experimental details.</caption><tbody><tr><td colspan="2"><strong>Crystal data</strong></td></tr><tr><td>Chemical formula</td><td>C<sub>22</sub>H<sub>29</sub>B<sub>10</sub>N</td></tr><tr><td>M<sub>r</sub></td><td>415.56</td></tr><tr><td>Crystal system, space group</td><td>Monoclinic, <i>P</i>2<sub>1</sub>/<i>c</i></td></tr><tr><td>Temperature (K)</td><td>130</td></tr><tr><td><i>a</i>, <i>b</i>, <i>c</i> (Å)</td><td>13.0128 (2), 27.1423 (4),<br>13.9114 (3)</td></tr><tr><td>β (°)</td><td>109.485 (2)</td></tr><tr><td><i>V</i> (Å<sup>3</sup>)</td><td>4632.07 (15)</td></tr><tr><td>Z</td><td>8</td></tr><tr><td>Radiation type</td><td>Mo Kα</td></tr><tr><td>μ (mm<sup>-1</sup>)</td><td>0.06</td></tr><tr><td>Crystal size (mm)</td><td>0.40 × 0.35 × 0.25</td></tr><tr><td colspan="2"><strong>Data collection</strong></td></tr><tr><td>Diffractometer</td><td>Xcalibur, Sapphire3, Gemini</td></tr><tr><td>Absorption correction</td><td>Multi-scan (<i>CrysAlis PRO</i>; Rigaku OD, 2020)</td></tr><tr><td><i>T</i><sub>min</sub>, <i>T</i><sub>max</sub></td><td>0.997, 1.000</td></tr><tr><td>No. of measured, independent and observed [<i>I</i> > 2σ(<i>I</i>)] reflections</td><td>76840, 15117, 9789</td></tr><tr><td><i>R</i><sub>int</sub></td><td>0.054</td></tr><tr><td>(sin θ/λ)<sub>max</sub> (Å<sup>-1</sup>)</td><td>0.745</td></tr><tr><td colspan="2"><strong>Refinement</strong></td></tr><tr><td><i>R</i>[<i>F</i><sup>2</sup> > 2σ(<i>F</i><sup>2</sup>)], <i>wR</i>(<i>F</i><sup>2</sup>), <i>S</i></td><td>0.056, 0.160, 1.02</td></tr><tr><td>No. of reflections</td><td>15117</td></tr><tr><td>No. of parameters</td><td>827</td></tr><tr><td>H-atom treatment</td><td>All H-atom parameters refined</td></tr><tr><td>Δρ<sub>max</sub>, Δρ<sub>min</sub> (e Å<sup>-3</sup>)</td><td>0.36, -0.25</td></tr></tbody></table>

Computer programs: *CrysAlis PRO* (Rigaku OD, 2020), *SHELXT2018-2* (Sheldrick, 2015a), *SHELXL2018-3* (Sheldrick, 2015b), *DIAMOND* (Crystal Impact GbR, 2022) and *WinGX* (Farrugia, 2012).

Taking the data of this structure determination automatically generated by the *CrysAlis PRO* software routine (Rigaku OD, 2020), the structure solution (monoclinic cell; space group *P*2<sub>1</sub>/<i>n</i>; Table 1) provided a disordered carborane unit, which can only be refined with a very limited accuracy and with unlocalizable carbon atoms of the carborane unit. Nevertheless, the final structure parameters for this cell setting (*R*<sub>1</sub> and *wR*<sub>2</sub> for all observed reflections: 0.0543 and 0.1268), the space group *P*2<sub>1</sub>/<i>n</i> and its associated extinction conditions didn't look suspicious, and for the remaining non-disordered fraction of the molecule, even all hydrogen atoms could be localized in the final step of the refinement. However, disordered structures should always be checked thoroughly, as disorder may be feigned and a result of an incorrect space group, twinning, an erroneous unit-cell determination, etc. For these reasons, the original recorded frames had been manually inspected as well. This inspection of the original data revealed a small number of additional very weak reflections, which had been ignored by the automated analysis and integration routine. As a representative, the reconstructed (hk2)-layer is given in Fig. 1. Analyzing all reflections the intensity distribution can be quantified by:

$$ \frac{\sum_{h \neq 2n} F^2_{o(hkl)}}{\sum_{h=2n} F^2_{o(hkl)}} = 0.091 $$

These additional reflections (h≠2n) represent approximately 8% of the total intensity. Taking these weak reflections into
<figure><img src="image_7.png" /><figcaption>**Figure 2**
The two molecules of the asymmetric unit (displacement ellipsoids are drawn at the 50% probability level; hydrogen atoms are omitted for clarity).</figcaption></figure>

account, the *a*-axis is doubled and a new modified unit cell is obtained, with parameters summarized in Table 2. To compare this larger unit cell with the initial cell of the automated data reduction routine given above, the cell setting of the small standard cell $a_1, b_1, c_1, \beta_1$ may be better transformed into its non-standard setting $a_2, b_2, c_2, \beta_2$ (Table 1).

With this larger cell, the structure could be solved with *SHELXT* (Sheldrick, 2015a) without any problems, whereby the two carborane clusters of the asymmetric unit are not disordered any longer. Without any doubt, all carbon atoms of both carborane units could be identified with a bond-length and displacement-parameter analysis, and in the final step,

even all hydrogen atoms could be localized, as expected for a light-atom structure. However, there is a strong resemblance between the two molecules of the asymmetric unit (Fig. 2) and it seems to be obvious to check the structure for pseudo-symmetry.

As illustrated with an overlay (Fig. 3), both molecules of the asymmetric unit represent more or less the same conformer, but the central carborane fragments C2/B1–B9 (molecule 1) and C24/B11–B19 (molecule 2) are clearly in a different position and can't be mapped to each other with a translation vector. However, these units are responsible for the enlarged unit cell, and the question arises as to the reason for these differently positioned carborane units. To answer this question, an analysis of intermolecular interactions of the two carboranes may be most expedient.

### 3. Supramolecular features

Numerous carborane structures have previously been analyzed and a very interesting summary on this topic was published by Fox & Hughes (2004). As a consequence of carbon and boron electronegativity differences, the CH moiety of a carborane cluster has moderate acidity, whereas the basicity is expected to be dominating for the BH fragment. Analyzing intermolecular contact distances, one of the most obvious and striking features of this structure is a relatively strong carborane–phenyl–$\pi$ (CH···$\pi C_6$) interaction (Fig. 4). For both molecules of the asymmetric unit, the CH moiety of the carborane in *para* position to the substituent R1 and R2 points directly towards the center of an adjacent boron-bonded phenyl ring interacting with the entire $\pi C_6$-system. For this kind of CH···$\pi C_6$ interactions, Kraka and co-workers (Zou *et al.*, 2018) calculated a bonding energy of –33 kJ mol$^{-1}$ (–7.9 kcal mol$^{-1}$) for an ideally centered CH donor with a centroid distance of 2.36 Å (i.e. 2.74 Å for each CH···$\pi C$). This energy represents approximately one tenth of an ordinary carbon–carbon single bond. The experimentally estimated CH···$\pi C$ contact distances are in the range of 2.68 (2) (d$_{min}$) to 2.86 (2) Å (d$_{max}$) for C1H···$\pi C and 2.68 (2) to 2.78 (2) Å for C23H···$\pi C$. It can be thus proven that all CH···$\pi C$ contact distances are shorter than the sum of the van der Waals radii (H: 1.2 Å, C: 1.7 Å). The mean CH···$\pi C$ distances of 2.76 (2) Å for C1 and 2.73 (2) Å for C23 are quite close to the value given by Kraka and co-workers (Zou *et al.*, 2018).

<figure><img src="image_8.png" /><figcaption>**Figure 3**
Overlay of molecule 1 (brown: B1–B10/C1–C22/N1) and molecule 2 (light brown: B11–B20/C23–C44/N2). Hydrogen atoms are omitted for clarity.</figcaption></figure>

<figure><img src="image_9.png" /><figcaption>**Figure 4**
Intermolecular carborane–phenyl–$\pi$ (CH···$\pi C_6$) interactions. [R1 = R2 = $C_6H_4$–N(CH$_2$–Ph)$_2$]. Symmetry codes as in Table 3 and x – 1, y, z.</figcaption></figure>
For the remaining two N-bonded benzyl substituents only weak CH<sub>2</sub>···C π-stacking with adjacent N-bonded benzyl substituents is detectable: CH16B···C22 = 2.87 (2) Å and CH38B···C44 = 2.83 (2) Å.

The intermolecular interactions discussed so far are domi-
nant and comparable for both molecules of the asymmetric
unit; they control the packing and can thus be used as an
explanation for the structurally related conformers as illu-
strated by the overlay shown in Fig. 3. To explain the different
orientation of the central carborane fragments (C2/B1–B9 and
C24/B11–B19), which is ultimately responsible for the
enlarged unit cell, we analyzed intermolecular carborane–
carborane interactions as well (Fig. 5). These non-conven-
tional dihydrogen bonds M–H···H–X, first discovered in
1996 by Robert H. Crabtree (Crabtree *et al.*, 1996), are bonds
formed between a proton donor X–H (X = halogen, chal-
cogen, pnictogen or even carbon) and a hydridic proton
acceptor M–H (M = metal, transition metal or boron), and it
is a well-known fact by now that these dihydrogen bonds may
contribute to intra- and intermolecular bonding. To quantify
this kind of interaction, molecular dynamics simulations
conducted by Hobza's group (Fanfrlík *et al.*, 2006) revealed
bonding energies of approximately –20 kJ mol<sup>–1</sup> (–4.8 kcal
mol<sup>–1</sup>).

For this structure, the shortest experimental intermolecular
CH···HB contacts are 2.49 (2) Å (H24···H8X) and 2.61 (2) Å
(H2···H18X), both slightly longer than the sum of the van der
Waals radii of 2.4 Å, indicating a quite weak and most likely
electrostatic interaction. Nevertheless, this interaction
provides the only striking argument for an ordered structure,
as steric interactions can clearly be excluded. Considering
steric arguments only, the CH fragment of the carborane
moiety may take every possible position by simply rotating the
entire carborane unit (rotational disorder). A theoretical
calculation conducted by Hobza and co-workers (Fanfrlík *et
al.*, 2006) on intermolecular interactions of biomolecules with
*closo*-1-carbadodecaboranes led to the observation that
carboranes favor the formation of CH···HB dihydrogen
bonds with biomolecules, with the C–H unit of the biomo-
lecule pointing preferably to the lower hemisphere position of
the carborane, the part of the carborane cage opposite to the
carbon atom. In addition, it is known that electrophiles attack
carborane boron atoms preferably in an opposite *para* posi-
tion to the carbon atom (Rudakov *et al.*, 2011). Considering
these facts, the observed alternating interaction illustrated in
Fig. 5 may be explainable: The boron atom in the *para* position
to C1 and C23 bears the substituent (Fig. 4). C1–H and C23–
H are strongly and highly symmetrically bonded to the adja-
cent π-system, fixing the carborane unit within the lattice.

<figure><img src="image_10.png" /><figcaption>**Figure 5**
Intermolecular carborane-carborane interactions. Symmetry code: (') *x* − 1, *y*, *z*.</figcaption></figure>

However, rotation of this unit along the C1B10 and C23B20
axis seems to be still possible so that the remaining CH units
C2H and C24H can interact *via* CH···HB contacts with the
most preferred neighboring BH units B18 and B8, as both of
these boron atoms are in a *para* position to a carborane carbon
atom.

A particularly interesting aspect of these non-conventional dihydrogen bonds is that linear B—H···H—X arrangements are an exception (Calhorda, 2000), and it is still questionable whether the hydrogen-donor bond is pointing towards the hydridic B—H bond rather than the hydrogen atom itself. For this structure, the C—H···H angles for the shortest contacts (C2—H2···H18X and C24—H24···H8X) range from 116 (1) to 118 (1)° (Fig. 5).

4. Database survey

To compare the contact distances with other *ortho*-carboranes,
we analyzed the Cambridge Structural Database (CSD;
Version 5.43, last update November 2021; Groom *et al.*, 2016)
for *ortho*-carboranes with comparable intermolecular
CH···π*C<sub>6</sub>* contact distances. The accuracy of all inter-
molecular hydrogen–π*C<sub>6</sub>* distances was improved by normal-
izing the C–H bond distances to 1.089 Å, a value derived
from neutron diffraction experiments (Allen & Bruno, 2010).
The results are summarized in Fig. 6. To get more hits, the
range of intermolecular interactions was expanded, so that the
mean values of the CH···π*C<sub>6</sub>* interactions are still smaller
than the sum of the van der Waals radii. The given data
represent approximately 6% of all published *ortho*-carboranes
with at least one phenyl fragment in the structure. 27% of all
published *ortho*-carborane-phenyl structures have at least one
short contact, illustrating the particular importance of this
interaction. In addition to the strength of the individual
CH···π*C<sub>6</sub>* interaction, represented by its contact distance,
Fig. 6 illustrates its symmetry: the smaller the range of the

<figure><img src="image_11.png" /><figcaption>**Figure 6**
Normalized (C–H = 1.089 Å) *ortho*-carborane CH···π*C<sub>6</sub>* contact distances (gray) published in the Cambridge Structural Database (CSD, version 5.43) with the corresponding CSD entry code. The experimental normalized CH···π*C<sub>6</sub>* contacts for C1 and C23 are highlighted in orange, and mean CH···π*C<sub>6</sub>* contacts are presented in red.</figcaption></figure>
<table><caption>**Table 3**
Hydrogen-bond geometry (Å, °).</caption><thead><tr><th>D-H···A</th><th>D-H</th><th>H···A</th><th>D···A</th><th>D-H···A</th></tr></thead><tbody><tr><td>C1-H1···C3<sup>i</sup></td><td>0.968 (17)</td><td>2.742 (17)</td><td>3.6196 (17)</td><td>151.0 (13)</td></tr><tr><td>C1-H1···C4<sup>i</sup></td><td>0.968 (17)</td><td>2.676 (17)</td><td>3.5889 (17)</td><td>157.3 (12)</td></tr><tr><td>C1-H1···C5<sup>i</sup></td><td>0.968 (17)</td><td>2.740 (17)</td><td>3.6322 (18)</td><td>153.4 (12)</td></tr><tr><td>C1-H1···C6<sup>i</sup></td><td>0.968 (17)</td><td>2.860 (17)</td><td>3.7008 (18)</td><td>145.8 (13)</td></tr><tr><td>C1-H1···C7<sup>i</sup></td><td>0.968 (17)</td><td>2.797 (17)</td><td>3.6112 (18)</td><td>142.2 (12)</td></tr><tr><td>C1-H1···C8<sup>i</sup></td><td>0.968 (17)</td><td>2.745 (16)</td><td>3.5809 (18)</td><td>144.9 (12)</td></tr><tr><td>C23-H23···C25<sup>i</sup></td><td>0.971 (16)</td><td>2.780 (16)</td><td>3.6436 (17)</td><td>148.4 (12)</td></tr><tr><td>C23-H23···C26<sup>i</sup></td><td>0.971 (16)</td><td>2.741 (15)</td><td>3.5682 (17)</td><td>143.4 (11)</td></tr><tr><td>C23-H23···C27<sup>i</sup></td><td>0.971 (16)</td><td>2.724 (15)</td><td>3.5432 (18)</td><td>142.3 (11)</td></tr><tr><td>C23-H23···C28<sup>i</sup></td><td>0.971 (16)</td><td>2.749 (16)</td><td>3.6050 (18)</td><td>147.3 (12)</td></tr><tr><td>C23-H23···C29<sup>i</sup></td><td>0.971 (16)</td><td>2.681 (16)</td><td>3.5857 (18)</td><td>155.0 (12)</td></tr><tr><td>C23-H23···C30<sup>i</sup></td><td>0.971 (16)</td><td>2.690 (16)</td><td>3.5996 (17)</td><td>156.0 (12)</td></tr></tbody></table>

Symmetry code: (i) $x, -y + \frac{1}{2}, z - \frac{1}{2}$.

individual CH···πC₆ contact distances are, the more centered and symmetrical the π-bonded system is. Quantitatively, this can be expressed with a delta value defined as $Δ = d_{max} - d_{min}$ (Fig. 7). The individual contact distances for C1 and C23 differ by only ± 0.09 Å and ± 0.05 Å from the mean value, indicating a very highly symmetrical interaction. Numerical details of the hydrogen bonds in the title structure are given in Table 3.

Finally, we compared intermolecular C-H···H···B contact distances between carboranes as well, as they are responsible for our ordered structure and the enlarged unit cell. To get more reliable values, we analyzed the CSD in a comparable manner by using normalized C-H (1.089 Å) and B-H (1.185 Å) bond lengths (Allen & Bruno, 2010). The two shortest normalized C-H···H···B contacts for our structure differ from the values given above: 2.438 (11) Å for H24···H8X and 2.539 (7) Å for H2···H18X. They are both slightly shorter as expected, but still longer than the sum of the van der Waals radii of 2.4 Å. For comparison, 21% of all *ortho*-carboranes published in the CSD exhibit much stronger interactions with contact distances ranging from 1.858 to 2.400 Å, indicating that short contacts are by no means exotic.

## 5. Summary

Intermolecular interactions play a crucial role in the molecular self-assembly of compounds, which is important in biological

<figure><img src="image_12.png" /><figcaption>**Figure 7**
Delta values (blue) of *ortho*-carborane CH···πC₆ contact distances defined as $Δ = d_{max} - d_{min}$. The experimental values for C1 and C23 are highlighted in orange.</figcaption></figure>

<figure><img src="image_13.png" /><figcaption>**Figure 8**
PLATON ADDSYM checkCIF validation alert.</figcaption></figure>

systems or in catalysis. It is noteworthy that substituted carboranes can form two types of non-covalent interactions: dihydrogen bonds or stacking interactions. In particular, di-hydrogen bonds of the B-H···H···X type are important for the binding of this class of compounds to biomolecules. Starting from *ortho*-carborane, promising ligands for homogeneous catalysis can be prepared by directed synthesis. The compound *closo*-9-[4-(dibenzylamino)phenyl]-1,2-dicarbado-decaborane(12) reported here can thus be used as a building block after deprotection of the amino group.

The detailed analysis of this structure determination revealed pseudo translation symmetry (PTS) and thus we can ignore the PLATON checkCIF (Spek, 2020) validation alert (Fig. 8). Without any doubt, the huge unit cell is the correct solution. The example given here clearly demonstrates that it is always important to check the original recorded data of a structure determination.

## 6. Synthesis and crystallization

All reactions were conducted under N₂. A solid mixture of Mg turnings (0.356 g, 14.6 mmol) and LiCl (0.364 g, 8.59 mmol) was stirred overnight to mechanically activate the Mg. 1,2-Dibromoethane (0.1 ml, 1.15 mmol) in THF (10 ml) was added slowly to further activate Mg. Then N,N-dibenzyl-4-bromoaniline (2.58 g, 7.33 mmol) in THF (15 ml) was added over 40 min. The reaction mixture was stirred for 18 h at rt and then slowly added to a solution of 9-iodo-*ortho*-carborane (0.592 g, 1.96 mmol) and [PdCl₂(PPh₃)₂] (0.045 g, 0.064 mmol) in THF (10 ml) over 15 min. The resulting mixture was stirred at rt for *ca* 5 d; the reaction progress was monitored by NMR spectroscopy. At the end of the reaction, the mixture was quenched with methanol (50 ml) and distilled water (100 ml), then poured into Et₂O (50 ml), and the phases were separated. The organic layer was washed with saturated sodium bicarbonate solution (20 ml), and the aqueous phase was extracted with Et₂O (4 × 50 ml). The combined organic layers were dried over MgSO₄. After evaporation of solvents, the remaining brown oil was purified by column chromatography on silica gel, using a Biotage Isolera ONE SNAP KP-SIL 100 g cartridge, 100 ml min⁻¹, n-hexane/ethyl acetate (97:3 to 40:60, v/v), yielding 0.492 g (1.18 mmol, 50%) of a colorless solid.
Crystals suitable for X-ray structure analysis were obtained
from dichloromethane and *n*-pentane by slow evaporation.

$R_F$ (n-hexane/ethyl acetate 85:15, v/v) = 0.25.

¹H NMR (400 MHz, CDCl₃, 298 K): δ = 7.34 to 7.28 (m, 4H, Bz-H), 7.27 to 7.23 (m, 6H, Bz-H), 7.17 (d, 2H, *J* = 8.3 Hz, C₆H₄), 6.65 (d, 2H, *J* = 8.3 Hz, C₆H₄), 4.61 (s, 4H, CH₂), 3.56 (s, 1H, Ccarborane—H), 3.45 (s, 1H, Ccarborane—H), 3.14 to 1.58 (m, 9H, BH) ppm.

¹³C[{¹H} NMR (101 MHz, CDCl₃, 298 K) δ = 148.9, 139.0, 133.4, 128.7, 126.9, 126.9, 111.8, 54.2, 52.9, 48.0 ppm.

¹¹B[{¹H} NMR (128 MHz, CDCl₃) δ = 8.3 (1B), -2.2 (1B), -8.7 (2B), -13.2 to -16.3 (6B) ppm.

¹¹B NMR (128 MHz, CDCl₃, 298 K): δ = 8.3 (s, 1B), -2.2 (d, 1B, ¹JBH = 149 Hz), -8.7 (d, 2B, ¹JBH = 151 Hz), -14.7 (m, 6B) ppm.

HRMS (ESI+) [C₂₂H₂₉B₁₀N], m/z calculated: 416.3387 ([M + H]⁺), m/z found: 416.3385 (100%).

6.1. Refinement

Crystal data, data collection and structure refinement
details are summarized in Table 2. All hydrogen atoms were
located in difference-Fourier maps and refined isotropically.
Distance restraints were applied only temporarily for
hydrogen atoms with normalized B—H and C—H carborane
bond lengths.

Funding information

The project leading to this application received funding from
the European Union's Horizon 2020 research and innovation
programme under the Marie Skłodowska-Curie grant agree-
ment No. 860322. This paper was funded by the Open Access

Publishing Fund of Leipzig University supported by the
German Research Foundation within the program Open
Access Publication Funding.

References

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Andrews, P. C., Hardie, M. J. & Raston, C. L. (1999). *Coord. Chem. Rev.* **189**, 169–198.

Calhorda, M. J. (2000). *Chem. Commun.* pp. 801–809.

Crabtree, R. H., Siegbahn, P. E. M., Eisenstein, O., Rheingold, A. L. & Koetzle, T. F. (1996). *Acc. Chem. Res.* **29**, 348–354.

Crystal Impact GbR. (2022). *DIAMOND*. Crystal Impact GbR, Bonn, Germany.

Fanfrlík, J., Lepšík, M., Horinek, D., Havlas, Z. & Hobza, P. (2006). *ChemPhysChem*, **7**, 1100–1105.

Farrugia, L. J. (2012). *J. Appl. Cryst.* **45**, 849–854.

Fox, M. A. & Hughes, A. K. (2004). *Coord. Chem. Rev.* **248**, 457–476.

Grimes, R. N. (2016). *Carboranes*, 3rd ed. London, Burlington, MA: Academic Press.

Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). *Acta Cryst.* **B72**, 171–179.

Linden, A. (2020). *Acta Cryst.* **E76**, 765–775.

Rigaku OD (2020). *CrysAlis PRO*. Rigaku Oxford Diffraction, Wroclaw, Poland.

Rudakov, D. A., Kurman, P. V. & Potkin, V. I. (2011). *Russ. J. Gen. Chem.* **81**, 1137–1142.

Sheldrick, G. M. (2015a). *Acta Cryst.* **A71**, 3–8.

Sheldrick, G. M. (2015b). *Acta Cryst.* **C71**, 3–8.

Spek, A. L. (2020). *Acta Cryst.* **E76**, 1–11.

Stockmann, P., Gozzi, M., Kuhnert, R., Sárosi, M. B. & Hey-Hawkins, E. (2019). *Chem. Soc. Rev.* **48**, 3497–3512.

Zakharkin, L. I., Kovredov, A. I., Ol'shevskaya, V. A. & Shaugum-bekova, Z. S. (1982). *J. Organomet. Chem.* **226**, 217–222.

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supporting information

Acta Cryst. (2022). E78 [https://doi.org/10.1107/S205698902201043X]

# Pitfalls of a structure determination: The structure of closo-9-[4-(dibenzyl-amino)phenyl]-1,2-dicarbadodecaborane(12)

Max Milewski, Anne-Marie Caminade, Evamarie Hey-Hawkins and Peter Lönnecke

## Computing details

Data collection: *CrysAlis PRO* (Rigaku OD, 2020); cell refinement: *CrysAlis PRO* (Rigaku OD, 2020); data reduction: *CrysAlis PRO* (Rigaku OD, 2020); program(s) used to solve structure: *SHELXT2018-2* (Sheldrick, 2015a); program(s) used to refine structure: *SHELXL2018-3* (Sheldrick, 2015b); molecular graphics: *DIAMOND* (Crystal Impact GbR, 2022); software used to prepare material for publication: *WinGX* (Farrugia, 2012).

## closo-9-[4-(Dibenzylamino)phenyl]-1,2-dicarbadodecaborane(12)

### Crystal data

C₂₂H₂₉B₁₀N
M_r = 415.56
Monoclinic, P2₁/c
a = 13.0128 (2) Å
b = 27.1423 (4) Å
c = 13.9114 (3) Å
β = 109.485 (2)°
V = 4632.07 (15) Å³
Z = 8

F(000) = 1744
Dₓ = 1.192 Mg m⁻³
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 15129 reflections
θ = 2.7–31.7°
μ = 0.06 mm⁻¹
T = 130 K
Prism, clear colourless
0.40 × 0.35 × 0.25 mm

### Data collection

Xcalibur, Sapphire3, Gemini
diffractometer
Radiation source: fine-focus sealed X-ray tube
Detector resolution: 16.3560 pixels mm⁻¹
ω scans
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2020)
T_min = 0.997, T_max = 1.000

76840 measured reflections
15117 independent reflections
9789 reflections with *I* > 2σ(*I*)
R int = 0.054
θ max = 32.0°, θ min = 2.2°
h = −18→18
k = −39→39
l = −20→19

### Refinement

Refinement on *F*²
Least-squares matrix: full
R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.160
S = 1.02
15117 reflections
827 parameters
0 restraints
Primary atom site location: dual

Secondary atom site location: difference Fourier map
Hydrogen site location: difference Fourier map
All H-atom parameters refined
w = 1/[σ²(F₀²) + (0.0768P)² + 0.5669P]
where P = (F₀² + 2F_c²)/3
(Δ/σ)max = 0.001
Δρmax = 0.36 e Å⁻³
Δρmin = −0.25 e Å⁻³
Special details

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

<table><caption>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)</caption><thead><tr><th></th><th>x</th><th>y</th><th>z</th><th>U<sub>iso</sub>*/U<sub>eq</sub></th></tr></thead><tbody><tr><td>N1</td><td>0.80689 (8)</td><td>0.44759 (4)</td><td>0.29624 (8)</td><td>0.0207 (2)</td></tr><tr><td>N2</td><td>0.31192 (8)</td><td>0.44924 (4)</td><td>0.29350 (8)</td><td>0.0202 (2)</td></tr><tr><td>C1</td><td>0.75073 (11)</td><td>0.21628 (5)</td><td>-0.18817 (10)</td><td>0.0246 (3)</td></tr><tr><td>C2</td><td>0.86438 (11)</td><td>0.22701 (6)</td><td>-0.09675 (11)</td><td>0.0270 (3)</td></tr><tr><td>C3</td><td>0.77687 (9)</td><td>0.33326 (4)</td><td>0.07952 (8)</td><td>0.0154 (2)</td></tr><tr><td>C4</td><td>0.68627 (9)</td><td>0.35885 (4)</td><td>0.08718 (9)</td><td>0.0164 (2)</td></tr><tr><td>C5</td><td>0.69507 (9)</td><td>0.39534 (4)</td><td>0.15909 (9)</td><td>0.0170 (2)</td></tr><tr><td>C6</td><td>0.79726 (9)</td><td>0.40888 (4)</td><td>0.22913 (8)</td><td>0.0163 (2)</td></tr><tr><td>C7</td><td>0.88796 (9)</td><td>0.38137 (4)</td><td>0.22642 (9)</td><td>0.0172 (2)</td></tr><tr><td>C8</td><td>0.87696 (9)</td><td>0.34536 (4)</td><td>0.15272 (9)</td><td>0.0168 (2)</td></tr><tr><td>C9</td><td>0.71200 (11)</td><td>0.47718 (5)</td><td>0.29057 (10)</td><td>0.0219 (3)</td></tr><tr><td>C10</td><td>0.66716 (10)</td><td>0.50871 (4)</td><td>0.19573 (9)</td><td>0.0191 (2)</td></tr><tr><td>C11</td><td>0.73030 (11)</td><td>0.52328 (5)</td><td>0.13796 (11)</td><td>0.0262 (3)</td></tr><tr><td>C12</td><td>0.68691 (11)</td><td>0.55325 (5)</td><td>0.05303 (12)</td><td>0.0286 (3)</td></tr><tr><td>C13</td><td>0.58003 (11)</td><td>0.56903 (5)</td><td>0.02561 (11)</td><td>0.0271 (3)</td></tr><tr><td>C14</td><td>0.51617 (11)</td><td>0.55469 (6)</td><td>0.08218 (12)</td><td>0.0330 (3)</td></tr><tr><td>C15</td><td>0.55940 (11)</td><td>0.52455 (6)</td><td>0.16659 (11)</td><td>0.0275 (3)</td></tr><tr><td>C16</td><td>0.91324 (10)</td><td>0.46443 (5)</td><td>0.36173 (9)</td><td>0.0199 (2)</td></tr><tr><td>C17</td><td>0.95759 (10)</td><td>0.43697 (5)</td><td>0.46178 (9)</td><td>0.0199 (2)</td></tr><tr><td>C18</td><td>0.89638 (11)</td><td>0.43253 (6)</td><td>0.52622 (10)</td><td>0.0286 (3)</td></tr><tr><td>C19</td><td>0.93807 (14)</td><td>0.40840 (6)</td><td>0.61920 (11)</td><td>0.0366 (4)</td></tr><tr><td>C20</td><td>1.04145 (16)</td><td>0.38851 (6)</td><td>0.64884 (12)</td><td>0.0429 (4)</td></tr><tr><td>C21</td><td>1.10342 (15)</td><td>0.39246 (7)</td><td>0.58564 (12)</td><td>0.0426 (4)</td></tr><tr><td>C22</td><td>1.06112 (12)</td><td>0.41662 (6)</td><td>0.49229 (11)</td><td>0.0310 (3)</td></tr><tr><td>C23</td><td>0.25860 (10)</td><td>0.20807 (5)</td><td>-0.16977 (10)</td><td>0.0218 (3)</td></tr><tr><td>C24</td><td>0.34621 (10)</td><td>0.25254 (5)</td><td>-0.14500 (10)</td><td>0.0214 (3)</td></tr><tr><td>C25</td><td>0.28131 (9)</td><td>0.33029 (4)</td><td>0.08712 (9)</td><td>0.0159 (2)</td></tr><tr><td>C26</td><td>0.38140 (9)</td><td>0.34356 (5)</td><td>0.15898 (9)</td><td>0.0173 (2)</td></tr><tr><td>C27</td><td>0.39249 (9)</td><td>0.38135 (5)</td><td>0.22885 (9)</td><td>0.0172 (2)</td></tr><tr><td>C28</td><td>0.30168 (9)</td><td>0.40946 (4)</td><td>0.22909 (8)</td><td>0.0163 (2)</td></tr><tr><td>C29</td><td>0.19968 (9)</td><td>0.39532 (5)</td><td>0.16005 (9)</td><td>0.0174 (2)</td></tr><tr><td>C30</td><td>0.19095 (9)</td><td>0.35701 (4)</td><td>0.09171 (9)</td><td>0.0165 (2)</td></tr><tr><td>C31</td><td>0.21668 (11)</td><td>0.47828 (5)</td><td>0.28924 (10)</td><td>0.0217 (3)</td></tr><tr><td>C32</td><td>0.16852 (10)</td><td>0.50898 (4)</td><td>0.19360 (9)</td><td>0.0184 (2)</td></tr><tr><td>C33</td><td>0.06146 (11)</td><td>0.52514 (6)</td><td>0.16785 (11)</td><td>0.0277 (3)</td></tr><tr><td>C34</td><td>0.01589 (11)</td><td>0.55504 (6)</td><td>0.08342 (12)</td><td>0.0338 (3)</td></tr><tr><td>C35</td><td>0.07650 (11)</td><td>0.56851 (5)</td><td>0.02323 (11)</td><td>0.0275 (3)</td></tr><tr><td>C36</td><td>0.18253 (11)</td><td>0.55209 (5)</td><td>0.04685 (11)</td><td>0.0263 (3)</td></tr><tr><td>C37</td><td>0.22841 (10)</td><td>0.52246 (5)</td><td>0.13193 (10)</td><td>0.0238 (3)</td></tr></tbody></table>
<table>
  <tr>
    <td>C38</td>
    <td>0.41834 (10)</td>
    <td>0.46511 (5)</td>
    <td>0.36040 (9)</td>
    <td>0.0206 (2)</td>
  </tr>
  <tr>
    <td>C39</td>
    <td>0.46056 (10)</td>
    <td>0.43727 (4)</td>
    <td>0.46019 (9)</td>
    <td>0.0191 (2)</td>
  </tr>
  <tr>
    <td>C40</td>
    <td>0.39592 (11)</td>
    <td>0.43183 (5)</td>
    <td>0.52134 (10)</td>
    <td>0.0240 (3)</td>
  </tr>
  <tr>
    <td>C41</td>
    <td>0.43545 (13)</td>
    <td>0.40825 (6)</td>
    <td>0.61522 (11)</td>
    <td>0.0301 (3)</td>
  </tr>
  <tr>
    <td>C42</td>
    <td>0.54040 (13)</td>
    <td>0.38950 (6)</td>
    <td>0.64855 (11)</td>
    <td>0.0344 (3)</td>
  </tr>
  <tr>
    <td>C43</td>
    <td>0.60498 (12)</td>
    <td>0.39415 (6)</td>
    <td>0.58822 (12)</td>
    <td>0.0327 (3)</td>
  </tr>
  <tr>
    <td>C44</td>
    <td>0.56558 (11)</td>
    <td>0.41789 (5)</td>
    <td>0.49431 (11)</td>
    <td>0.0258 (3)</td>
  </tr>
  <tr>
    <td>B1</td>
    <td>0.81698 (12)</td>
    <td>0.27055 (6)</td>
    <td>-0.18993 (12)</td>
    <td>0.0267 (3)</td>
  </tr>
  <tr>
    <td>B2</td>
    <td>0.67398 (12)</td>
    <td>0.26766 (6)</td>
    <td>-0.22070 (11)</td>
    <td>0.0241 (3)</td>
  </tr>
  <tr>
    <td>B3</td>
    <td>0.64289 (12)</td>
    <td>0.22044 (6)</td>
    <td>-0.14670 (12)</td>
    <td>0.0244 (3)</td>
  </tr>
  <tr>
    <td>B4</td>
    <td>0.76566 (14)</td>
    <td>0.19313 (6)</td>
    <td>-0.06946 (12)</td>
    <td>0.0279 (3)</td>
  </tr>
  <tr>
    <td>B5</td>
    <td>0.84362 (12)</td>
    <td>0.23900 (6)</td>
    <td>0.01495 (11)</td>
    <td>0.0246 (3)</td>
  </tr>
  <tr>
    <td>B6</td>
    <td>0.87445 (11)</td>
    <td>0.28651 (6)</td>
    <td>-0.05933 (12)</td>
    <td>0.0236 (3)</td>
  </tr>
  <tr>
    <td>B7</td>
    <td>0.75088 (12)</td>
    <td>0.31360 (6)</td>
    <td>-0.13680 (11)</td>
    <td>0.0215 (3)</td>
  </tr>
  <tr>
    <td>B8</td>
    <td>0.64304 (11)</td>
    <td>0.28275 (6)</td>
    <td>-0.10971 (10)</td>
    <td>0.0201 (3)</td>
  </tr>
  <tr>
    <td>B9</td>
    <td>0.69944 (12)</td>
    <td>0.23639 (6)</td>
    <td>-0.01608 (11)</td>
    <td>0.0222 (3)</td>
  </tr>
  <tr>
    <td>B10</td>
    <td>0.76666 (10)</td>
    <td>0.29471 (5)</td>
    <td>-0.00781 (10)</td>
    <td>0.0162 (2)</td>
  </tr>
  <tr>
    <td>B11</td>
    <td>0.36914 (12)</td>
    <td>0.20502 (6)</td>
    <td>-0.05926 (12)</td>
    <td>0.0228 (3)</td>
  </tr>
  <tr>
    <td>B12</td>
    <td>0.23609 (12)</td>
    <td>0.18860 (6)</td>
    <td>-0.06331 (12)</td>
    <td>0.0234 (3)</td>
  </tr>
  <tr>
    <td>B13</td>
    <td>0.14027 (11)</td>
    <td>0.22585 (6)</td>
    <td>-0.15496 (11)</td>
    <td>0.0231 (3)</td>
  </tr>
  <tr>
    <td>B14</td>
    <td>0.21202 (12)</td>
    <td>0.26605 (6)</td>
    <td>-0.21025 (11)</td>
    <td>0.0238 (3)</td>
  </tr>
  <tr>
    <td>B15</td>
    <td>0.29526 (12)</td>
    <td>0.30483 (6)</td>
    <td>-0.11260 (11)</td>
    <td>0.0221 (3)</td>
  </tr>
  <tr>
    <td>B16</td>
    <td>0.39070 (11)</td>
    <td>0.26741 (6)</td>
    <td>-0.01958 (11)</td>
    <td>0.0208 (3)</td>
  </tr>
  <tr>
    <td>B17</td>
    <td>0.31821 (11)</td>
    <td>0.22730 (5)</td>
    <td>0.03513 (11)</td>
    <td>0.0198 (3)</td>
  </tr>
  <tr>
    <td>B18</td>
    <td>0.17675 (11)</td>
    <td>0.24009 (5)</td>
    <td>-0.02374 (11)</td>
    <td>0.0193 (3)</td>
  </tr>
  <tr>
    <td>B19</td>
    <td>0.16218 (11)</td>
    <td>0.28806 (6)</td>
    <td>-0.11484 (11)</td>
    <td>0.0206 (3)</td>
  </tr>
  <tr>
    <td>B20</td>
    <td>0.27214 (10)</td>
    <td>0.28968 (5)</td>
    <td>0.00406 (10)</td>
    <td>0.0160 (2)</td>
  </tr>
  <tr>
    <td>H1X</td>
    <td>0.8580 (12)</td>
    <td>0.2750 (6)</td>
    <td>-0.2448 (12)</td>
    <td>0.032 (4)*</td>
  </tr>
  <tr>
    <td>H2X</td>
    <td>0.6239 (12)</td>
    <td>0.2718 (6)</td>
    <td>-0.2989 (12)</td>
    <td>0.030 (4)*</td>
  </tr>
  <tr>
    <td>H3X</td>
    <td>0.5742 (13)</td>
    <td>0.1967 (6)</td>
    <td>-0.1808 (13)</td>
    <td>0.038 (5)*</td>
  </tr>
  <tr>
    <td>H4X</td>
    <td>0.7798 (12)</td>
    <td>0.1543 (6)</td>
    <td>-0.0584 (12)</td>
    <td>0.036 (4)*</td>
  </tr>
  <tr>
    <td>H5X</td>
    <td>0.9079 (12)</td>
    <td>0.2265 (6)</td>
    <td>0.0857 (12)</td>
    <td>0.030 (4)*</td>
  </tr>
  <tr>
    <td>H6X</td>
    <td>0.9525 (12)</td>
    <td>0.3046 (6)</td>
    <td>-0.0336 (12)</td>
    <td>0.033 (4)*</td>
  </tr>
  <tr>
    <td>H7X</td>
    <td>0.7472 (11)</td>
    <td>0.3518 (6)</td>
    <td>-0.1578 (11)</td>
    <td>0.028 (4)*</td>
  </tr>
  <tr>
    <td>H8X</td>
    <td>0.5659 (11)</td>
    <td>0.3021 (5)</td>
    <td>-0.1150 (11)</td>
    <td>0.022 (4)*</td>
  </tr>
  <tr>
    <td>H9X</td>
    <td>0.6610 (11)</td>
    <td>0.2233 (6)</td>
    <td>0.0401 (11)</td>
    <td>0.027 (4)*</td>
  </tr>
  <tr>
    <td>H11X</td>
    <td>0.4329 (11)</td>
    <td>0.1785 (6)</td>
    <td>-0.0585 (11)</td>
    <td>0.026 (4)*</td>
  </tr>
  <tr>
    <td>H12X</td>
    <td>0.2193 (13)</td>
    <td>0.1499 (6)</td>
    <td>-0.0566 (12)</td>
    <td>0.039 (5)*</td>
  </tr>
  <tr>
    <td>H13X</td>
    <td>0.0655 (12)</td>
    <td>0.2102 (6)</td>
    <td>-0.2046 (12)</td>
    <td>0.031 (4)*</td>
  </tr>
  <tr>
    <td>H14X</td>
    <td>0.1897 (11)</td>
    <td>0.2745 (5)</td>
    <td>-0.2911 (11)</td>
    <td>0.026 (4)*</td>
  </tr>
  <tr>
    <td>H15X</td>
    <td>0.3223 (12)</td>
    <td>0.3398 (6)</td>
    <td>-0.1329 (11)</td>
    <td>0.028 (4)*</td>
  </tr>
  <tr>
    <td>H16X</td>
    <td>0.4741 (12)</td>
    <td>0.2797 (6)</td>
    <td>0.0143 (12)</td>
    <td>0.033 (4)*</td>
  </tr>
  <tr>
    <td>H17X</td>
    <td>0.3546 (12)</td>
    <td>0.2139 (6)</td>
    <td>0.1164 (11)</td>
    <td>0.029 (4)*</td>
  </tr>
  <tr>
    <td>H18X</td>
    <td>0.1184 (12)</td>
    <td>0.2351 (6)</td>
    <td>0.0184 (12)</td>
    <td>0.030 (4)*</td>
  </tr>
  <tr>
    <td>H19X</td>
    <td>0.0949 (11)</td>
    <td>0.3153 (6)</td>
    <td>-0.1341 (11)</td>
    <td>0.027 (4)*</td>
  </tr>
  <tr>
    <td>H1</td>
    <td>0.7538 (12)</td>
    <td>0.1918 (6)</td>
    <td>-0.2379 (12)</td>
    <td>0.036 (4)*</td>
  </tr>
  <tr>
    <td>H2</td>
    <td>0.9255 (13)</td>
    <td>0.2086 (7)</td>
    <td>-0.1008 (13)</td>
    <td>0.042 (5)*</td>
  </tr>
  <tr>
    <td>H4</td>
    <td>0.6116 (11)</td>
    <td>0.3516 (5)</td>
    <td>0.0389 (11)</td>
    <td>0.021 (4)*</td>
  </tr>
</table>
<table><tr><td>H5</td><td>0.6312 (12)</td><td>0.4128 (6)</td><td>0.1600 (12)</td><td>0.025 (4)*</td></tr><tr><td>H7</td><td>0.9619 (11)</td><td>0.3872 (6)</td><td>0.2760 (11)</td><td>0.023 (4)*</td></tr><tr><td>H8</td><td>0.9449 (11)</td><td>0.3278 (5)</td><td>0.1528 (11)</td><td>0.019 (4)*</td></tr><tr><td>H9A</td><td>0.6543 (11)</td><td>0.4553 (5)</td><td>0.2997 (11)</td><td>0.018 (3)*</td></tr><tr><td>H9B</td><td>0.7361 (12)</td><td>0.4983 (6)</td><td>0.3542 (12)</td><td>0.028 (4)*</td></tr><tr><td>H11</td><td>0.8060 (14)</td><td>0.5123 (6)</td><td>0.1576 (13)</td><td>0.039 (5)*</td></tr><tr><td>H12</td><td>0.7323 (14)</td><td>0.5641 (7)</td><td>0.0159 (14)</td><td>0.045 (5)*</td></tr><tr><td>H13</td><td>0.5513 (13)</td><td>0.5901 (6)</td><td>-0.0343 (13)</td><td>0.034 (4)*</td></tr><tr><td>H14</td><td>0.4381 (17)</td><td>0.5653 (7)</td><td>0.0618 (16)</td><td>0.059 (6)*</td></tr><tr><td>H15</td><td>0.5134 (13)</td><td>0.5139 (6)</td><td>0.2062 (13)</td><td>0.035 (4)*</td></tr><tr><td>H16A</td><td>0.9674 (11)</td><td>0.4625 (5)</td><td>0.3246 (11)</td><td>0.020 (4)*</td></tr><tr><td>H16B</td><td>0.9041 (12)</td><td>0.5000 (6)</td><td>0.3739 (12)</td><td>0.025 (4)*</td></tr><tr><td>H18</td><td>0.8217 (13)</td><td>0.4463 (6)</td><td>0.5087 (13)</td><td>0.034 (4)*</td></tr><tr><td>H19</td><td>0.8947 (14)</td><td>0.4055 (7)</td><td>0.6620 (14)</td><td>0.043 (5)*</td></tr><tr><td>H20</td><td>1.0707 (16)</td><td>0.3727 (8)</td><td>0.7129 (16)</td><td>0.061 (6)*</td></tr><tr><td>H21</td><td>1.1814 (17)</td><td>0.3786 (8)</td><td>0.6078 (16)</td><td>0.067 (6)*</td></tr><tr><td>H22</td><td>1.1078 (15)</td><td>0.4198 (7)</td><td>0.4462 (15)</td><td>0.050 (5)*</td></tr><tr><td>H23</td><td>0.2607 (12)</td><td>0.1850 (6)</td><td>-0.2226 (12)</td><td>0.028 (4)*</td></tr><tr><td>H24</td><td>0.3953 (12)</td><td>0.2530 (6)</td><td>-0.1860 (12)</td><td>0.028 (4)*</td></tr><tr><td>H26</td><td>0.4469 (11)</td><td>0.3260 (5)</td><td>0.1611 (11)</td><td>0.020 (4)*</td></tr><tr><td>H27</td><td>0.4639 (11)</td><td>0.3874 (5)</td><td>0.2778 (11)</td><td>0.019 (4)*</td></tr><tr><td>H29</td><td>0.1364 (12)</td><td>0.4140 (6)</td><td>0.1593 (11)</td><td>0.024 (4)*</td></tr><tr><td>H30</td><td>0.1154 (11)</td><td>0.3494 (5)</td><td>0.0421 (11)</td><td>0.022 (4)*</td></tr><tr><td>H31A</td><td>0.1579 (12)</td><td>0.4560 (6)</td><td>0.2987 (12)</td><td>0.027 (4)*</td></tr><tr><td>H31B</td><td>0.2407 (11)</td><td>0.5004 (6)</td><td>0.3487 (12)</td><td>0.025 (4)*</td></tr><tr><td>H33</td><td>0.0171 (13)</td><td>0.5149 (6)</td><td>0.2090 (13)</td><td>0.037 (5)*</td></tr><tr><td>H34</td><td>-0.0609 (16)</td><td>0.5670 (7)</td><td>0.0671 (15)</td><td>0.051 (5)*</td></tr><tr><td>H35</td><td>0.0450 (13)</td><td>0.5902 (6)</td><td>-0.0366 (13)</td><td>0.036 (5)*</td></tr><tr><td>H36</td><td>0.2273 (14)</td><td>0.5614 (6)</td><td>0.0073 (14)</td><td>0.040 (5)*</td></tr><tr><td>H37</td><td>0.3018 (14)</td><td>0.5112 (6)</td><td>0.1469 (13)</td><td>0.039 (5)*</td></tr><tr><td>H38A</td><td>0.4750 (11)</td><td>0.4635 (6)</td><td>0.3239 (11)</td><td>0.022 (4)*</td></tr><tr><td>H38B</td><td>0.4126 (11)</td><td>0.5004 (6)</td><td>0.3745 (11)</td><td>0.024 (4)*</td></tr><tr><td>H40</td><td>0.3188 (13)</td><td>0.4444 (6)</td><td>0.5003 (12)</td><td>0.031 (4)*</td></tr><tr><td>H41</td><td>0.3875 (14)</td><td>0.4054 (7)</td><td>0.6553 (14)</td><td>0.045 (5)*</td></tr><tr><td>H42</td><td>0.5671 (14)</td><td>0.3733 (7)</td><td>0.7151 (14)</td><td>0.047 (5)*</td></tr><tr><td>H43</td><td>0.6804 (14)</td><td>0.3819 (7)</td><td>0.6116 (13)</td><td>0.040 (5)*</td></tr><tr><td>H44</td><td>0.6132 (13)</td><td>0.4216 (6)</td><td>0.4507 (13)</td><td>0.034 (4)*</td></tr></table>

Atomic displacement parameters (Å²)

<table><thead><tr><th></th><th>U<sup>11</sup></th><th>U<sup>22</sup></th><th>U<sup>33</sup></th><th>U<sup>12</sup></th><th>U<sup>13</sup></th><th>U<sup>23</sup></th></tr></thead><tbody><tr><td>N1</td><td>0.0218 (5)</td><td>0.0188 (5)</td><td>0.0181 (5)</td><td>0.0044 (4)</td><td>0.0019 (4)</td><td>-0.0056 (4)</td></tr><tr><td>N2</td><td>0.0224 (5)</td><td>0.0184 (5)</td><td>0.0160 (5)</td><td>0.0045 (4)</td><td>0.0013 (4)</td><td>-0.0040 (4)</td></tr><tr><td>C1</td><td>0.0259 (6)</td><td>0.0271 (7)</td><td>0.0219 (6)</td><td>-0.0025 (5)</td><td>0.0094 (5)</td><td>-0.0116 (5)</td></tr><tr><td>C2</td><td>0.0216 (6)</td><td>0.0330 (8)</td><td>0.0258 (7)</td><td>0.0032 (5)</td><td>0.0070 (5)</td><td>-0.0112 (6)</td></tr><tr><td>C3</td><td>0.0167 (5)</td><td>0.0158 (6)</td><td>0.0129 (5)</td><td>0.0002 (4)</td><td>0.0040 (4)</td><td>-0.0003 (4)</td></tr><tr><td>C4</td><td>0.0162 (5)</td><td>0.0160 (6)</td><td>0.0158 (5)</td><td>0.0000 (4)</td><td>0.0037 (4)</td><td>0.0002 (4)</td></tr><tr><td>C5</td><td>0.0169 (5)</td><td>0.0167 (6)</td><td>0.0169 (5)</td><td>0.0027 (4)</td><td>0.0049 (4)</td><td>-0.0003 (4)</td></tr></tbody></table>
<table>
  <tr>
    <td>C6</td>
    <td>0.0198 (5)</td>
    <td>0.0156 (6)</td>
    <td>0.0123 (5)</td>
    <td>0.0011 (4)</td>
    <td>0.0037 (4)</td>
    <td>0.0003 (4)</td>
  </tr>
  <tr>
    <td>C7</td>
    <td>0.0174 (5)</td>
    <td>0.0184 (6)</td>
    <td>0.0140 (5)</td>
    <td>0.0011 (4)</td>
    <td>0.0029 (4)</td>
    <td>-0.0014 (4)</td>
  </tr>
  <tr>
    <td>C8</td>
    <td>0.0159 (5)</td>
    <td>0.0183 (6)</td>
    <td>0.0151 (5)</td>
    <td>0.0017 (4)</td>
    <td>0.0037 (4)</td>
    <td>-0.0004 (4)</td>
  </tr>
  <tr>
    <td>C9</td>
    <td>0.0266 (6)</td>
    <td>0.0218 (6)</td>
    <td>0.0172 (6)</td>
    <td>0.0073 (5)</td>
    <td>0.0075 (5)</td>
    <td>-0.0004 (5)</td>
  </tr>
  <tr>
    <td>C10</td>
    <td>0.0222 (5)</td>
    <td>0.0156 (6)</td>
    <td>0.0182 (6)</td>
    <td>0.0017 (4)</td>
    <td>0.0050 (4)</td>
    <td>-0.0017 (5)</td>
  </tr>
  <tr>
    <td>C11</td>
    <td>0.0224 (6)</td>
    <td>0.0281 (7)</td>
    <td>0.0299 (7)</td>
    <td>0.0034 (5)</td>
    <td>0.0109 (5)</td>
    <td>0.0053 (6)</td>
  </tr>
  <tr>
    <td>C12</td>
    <td>0.0297 (7)</td>
    <td>0.0278 (7)</td>
    <td>0.0319 (7)</td>
    <td>-0.0003 (6)</td>
    <td>0.0151 (6)</td>
    <td>0.0070 (6)</td>
  </tr>
  <tr>
    <td>C13</td>
    <td>0.0302 (7)</td>
    <td>0.0231 (7)</td>
    <td>0.0261 (7)</td>
    <td>-0.0007 (5)</td>
    <td>0.0069 (5)</td>
    <td>0.0079 (6)</td>
  </tr>
  <tr>
    <td>C14</td>
    <td>0.0231 (6)</td>
    <td>0.0370 (9)</td>
    <td>0.0375 (8)</td>
    <td>0.0051 (6)</td>
    <td>0.0081 (6)</td>
    <td>0.0150 (7)</td>
  </tr>
  <tr>
    <td>C15</td>
    <td>0.0238 (6)</td>
    <td>0.0313 (8)</td>
    <td>0.0295 (7)</td>
    <td>0.0047 (5)</td>
    <td>0.0115 (5)</td>
    <td>0.0092 (6)</td>
  </tr>
  <tr>
    <td>C16</td>
    <td>0.0248 (6)</td>
    <td>0.0166 (6)</td>
    <td>0.0161 (5)</td>
    <td>-0.0012 (5)</td>
    <td>0.0038 (5)</td>
    <td>-0.0012 (5)</td>
  </tr>
  <tr>
    <td>C17</td>
    <td>0.0244 (6)</td>
    <td>0.0165 (6)</td>
    <td>0.0162 (5)</td>
    <td>-0.0021 (5)</td>
    <td>0.0035 (5)</td>
    <td>-0.0035 (5)</td>
  </tr>
  <tr>
    <td>C18</td>
    <td>0.0268 (6)</td>
    <td>0.0369 (8)</td>
    <td>0.0203 (6)</td>
    <td>-0.0060 (6)</td>
    <td>0.0055 (5)</td>
    <td>-0.0013 (6)</td>
  </tr>
  <tr>
    <td>C19</td>
    <td>0.0473 (9)</td>
    <td>0.0419 (10)</td>
    <td>0.0201 (7)</td>
    <td>-0.0125 (7)</td>
    <td>0.0106 (6)</td>
    <td>0.0007 (6)</td>
  </tr>
  <tr>
    <td>C20</td>
    <td>0.0665 (11)</td>
    <td>0.0335 (9)</td>
    <td>0.0209 (7)</td>
    <td>0.0075 (8)</td>
    <td>0.0042 (7)</td>
    <td>0.0065 (7)</td>
  </tr>
  <tr>
    <td>C21</td>
    <td>0.0522 (10)</td>
    <td>0.0435 (10)</td>
    <td>0.0262 (7)</td>
    <td>0.0232 (8)</td>
    <td>0.0051 (7)</td>
    <td>0.0037 (7)</td>
  </tr>
  <tr>
    <td>C22</td>
    <td>0.0353 (7)</td>
    <td>0.0334 (8)</td>
    <td>0.0229 (7)</td>
    <td>0.0122 (6)</td>
    <td>0.0079 (6)</td>
    <td>-0.0010 (6)</td>
  </tr>
  <tr>
    <td>C23</td>
    <td>0.0238 (6)</td>
    <td>0.0220 (6)</td>
    <td>0.0215 (6)</td>
    <td>-0.0043 (5)</td>
    <td>0.0099 (5)</td>
    <td>-0.0083 (5)</td>
  </tr>
  <tr>
    <td>C24</td>
    <td>0.0225 (6)</td>
    <td>0.0229 (6)</td>
    <td>0.0220 (6)</td>
    <td>-0.0044 (5)</td>
    <td>0.0115 (5)</td>
    <td>-0.0054 (5)</td>
  </tr>
  <tr>
    <td>C25</td>
    <td>0.0183 (5)</td>
    <td>0.0157 (6)</td>
    <td>0.0138 (5)</td>
    <td>0.0000 (4)</td>
    <td>0.0054 (4)</td>
    <td>-0.0004 (4)</td>
  </tr>
  <tr>
    <td>C26</td>
    <td>0.0172 (5)</td>
    <td>0.0191 (6)</td>
    <td>0.0157 (5)</td>
    <td>0.0014 (4)</td>
    <td>0.0055 (4)</td>
    <td>-0.0010 (5)</td>
  </tr>
  <tr>
    <td>C27</td>
    <td>0.0174 (5)</td>
    <td>0.0182 (6)</td>
    <td>0.0142 (5)</td>
    <td>0.0000 (4)</td>
    <td>0.0031 (4)</td>
    <td>-0.0010 (4)</td>
  </tr>
  <tr>
    <td>C28</td>
    <td>0.0212 (5)</td>
    <td>0.0143 (5)</td>
    <td>0.0123 (5)</td>
    <td>0.0015 (4)</td>
    <td>0.0043 (4)</td>
    <td>0.0011 (4)</td>
  </tr>
  <tr>
    <td>C29</td>
    <td>0.0175 (5)</td>
    <td>0.0171 (6)</td>
    <td>0.0171 (5)</td>
    <td>0.0027 (4)</td>
    <td>0.0051 (4)</td>
    <td>0.0005 (4)</td>
  </tr>
  <tr>
    <td>C30</td>
    <td>0.0174 (5)</td>
    <td>0.0164 (6)</td>
    <td>0.0149 (5)</td>
    <td>-0.0007 (4)</td>
    <td>0.0041 (4)</td>
    <td>-0.0007 (4)</td>
  </tr>
  <tr>
    <td>C31</td>
    <td>0.0291 (6)</td>
    <td>0.0199 (6)</td>
    <td>0.0160 (6)</td>
    <td>0.0072 (5)</td>
    <td>0.0072 (5)</td>
    <td>-0.0004 (5)</td>
  </tr>
  <tr>
    <td>C32</td>
    <td>0.0219 (5)</td>
    <td>0.0152 (6)</td>
    <td>0.0169 (5)</td>
    <td>0.0019 (4)</td>
    <td>0.0050 (4)</td>
    <td>-0.0004 (4)</td>
  </tr>
  <tr>
    <td>C33</td>
    <td>0.0251 (6)</td>
    <td>0.0312 (8)</td>
    <td>0.0303 (7)</td>
    <td>0.0054 (5)</td>
    <td>0.0138 (6)</td>
    <td>0.0091 (6)</td>
  </tr>
  <tr>
    <td>C34</td>
    <td>0.0231 (6)</td>
    <td>0.0385 (9)</td>
    <td>0.0386 (8)</td>
    <td>0.0086 (6)</td>
    <td>0.0087 (6)</td>
    <td>0.0157 (7)</td>
  </tr>
  <tr>
    <td>C35</td>
    <td>0.0271 (6)</td>
    <td>0.0246 (7)</td>
    <td>0.0274 (7)</td>
    <td>0.0014 (5)</td>
    <td>0.0047 (5)</td>
    <td>0.0088 (6)</td>
  </tr>
  <tr>
    <td>C36</td>
    <td>0.0276 (6)</td>
    <td>0.0262 (7)</td>
    <td>0.0265 (7)</td>
    <td>0.0006 (5)</td>
    <td>0.0109 (5)</td>
    <td>0.0071 (6)</td>
  </tr>
  <tr>
    <td>C37</td>
    <td>0.0210 (6)</td>
    <td>0.0245 (7)</td>
    <td>0.0259 (6)</td>
    <td>0.0023 (5)</td>
    <td>0.0078 (5)</td>
    <td>0.0035 (5)</td>
  </tr>
  <tr>
    <td>C38</td>
    <td>0.0262 (6)</td>
    <td>0.0160 (6)</td>
    <td>0.0165 (5)</td>
    <td>-0.0019 (5)</td>
    <td>0.0032 (5)</td>
    <td>-0.0026 (5)</td>
  </tr>
  <tr>
    <td>C39</td>
    <td>0.0221 (5)</td>
    <td>0.0156 (6)</td>
    <td>0.0160 (5)</td>
    <td>-0.0024 (4)</td>
    <td>0.0016 (4)</td>
    <td>-0.0035 (4)</td>
  </tr>
  <tr>
    <td>C40</td>
    <td>0.0255 (6)</td>
    <td>0.0254 (7)</td>
    <td>0.0193 (6)</td>
    <td>-0.0009 (5)</td>
    <td>0.0052 (5)</td>
    <td>0.0000 (5)</td>
  </tr>
  <tr>
    <td>C41</td>
    <td>0.0387 (8)</td>
    <td>0.0306 (8)</td>
    <td>0.0194 (6)</td>
    <td>-0.0033 (6)</td>
    <td>0.0077 (6)</td>
    <td>0.0020 (6)</td>
  </tr>
  <tr>
    <td>C42</td>
    <td>0.0460 (9)</td>
    <td>0.0274 (8)</td>
    <td>0.0205 (7)</td>
    <td>0.0012 (6)</td>
    <td>-0.0015 (6)</td>
    <td>0.0039 (6)</td>
  </tr>
  <tr>
    <td>C43</td>
    <td>0.0308 (7)</td>
    <td>0.0274 (8)</td>
    <td>0.0300 (7)</td>
    <td>0.0067 (6)</td>
    <td>-0.0029 (6)</td>
    <td>-0.0005 (6)</td>
  </tr>
  <tr>
    <td>C44</td>
    <td>0.0241 (6)</td>
    <td>0.0246 (7)</td>
    <td>0.0254 (7)</td>
    <td>0.0016 (5)</td>
    <td>0.0041 (5)</td>
    <td>-0.0035 (5)</td>
  </tr>
  <tr>
    <td>B1</td>
    <td>0.0263 (7)</td>
    <td>0.0345 (9)</td>
    <td>0.0227 (7)</td>
    <td>-0.0052 (6)</td>
    <td>0.0128 (6)</td>
    <td>-0.0079 (6)</td>
  </tr>
  <tr>
    <td>B2</td>
    <td>0.0250 (7)</td>
    <td>0.0307 (8)</td>
    <td>0.0160 (6)</td>
    <td>-0.0014 (6)</td>
    <td>0.0061 (5)</td>
    <td>-0.0045 (6)</td>
  </tr>
  <tr>
    <td>B3</td>
    <td>0.0242 (7)</td>
    <td>0.0263 (8)</td>
    <td>0.0229 (7)</td>
    <td>-0.0064 (6)</td>
    <td>0.0081 (6)</td>
    <td>-0.0082 (6)</td>
  </tr>
  <tr>
    <td>B4</td>
    <td>0.0370 (8)</td>
    <td>0.0205 (8)</td>
    <td>0.0247 (7)</td>
    <td>0.0018 (6)</td>
    <td>0.0084 (6)</td>
    <td>-0.0042 (6)</td>
  </tr>
  <tr>
    <td>B5</td>
    <td>0.0269 (7)</td>
    <td>0.0243 (8)</td>
    <td>0.0202 (7)</td>
    <td>0.0056 (6)</td>
    <td>0.0048 (6)</td>
    <td>-0.0036 (6)</td>
  </tr>
  <tr>
    <td>B6</td>
    <td>0.0193 (6)</td>
    <td>0.0296 (8)</td>
    <td>0.0226 (7)</td>
    <td>-0.0025 (6)</td>
    <td>0.0077 (5)</td>
    <td>-0.0082 (6)</td>
  </tr>
  <tr>
    <td>B7</td>
    <td>0.0249 (6)</td>
    <td>0.0238 (7)</td>
    <td>0.0163 (6)</td>
    <td>-0.0028 (6)</td>
    <td>0.0074 (5)</td>
    <td>-0.0008 (5)</td>
  </tr>
  <tr>
    <td>B8</td>
    <td>0.0170 (6)</td>
    <td>0.0257 (7)</td>
    <td>0.0165 (6)</td>
    <td>-0.0007 (5)</td>
    <td>0.0042 (5)</td>
    <td>-0.0051 (5)</td>
  </tr>
  <tr>
    <td>B9</td>
    <td>0.0277 (7)</td>
    <td>0.0204 (7)</td>
    <td>0.0202 (6)</td>
    <td>-0.0037 (6)</td>
    <td>0.0103 (6)</td>
    <td>-0.0026 (6)</td>
  </tr>
</table>
<table><tr><td>B10</td><td>0.0154 (5)</td><td>0.0173 (6)</td><td>0.0157 (6)</td><td>-0.0002 (5)</td><td>0.0050 (5)</td><td>-0.0020 (5)</td></tr><tr><td>B11</td><td>0.0217 (6)</td><td>0.0224 (7)</td><td>0.0250 (7)</td><td>0.0011 (5)</td><td>0.0089 (5)</td><td>-0.0039 (6)</td></tr><tr><td>B12</td><td>0.0291 (7)</td><td>0.0180 (7)</td><td>0.0252 (7)</td><td>-0.0028 (6)</td><td>0.0121 (6)</td><td>-0.0040 (6)</td></tr><tr><td>B13</td><td>0.0196 (6)</td><td>0.0295 (8)</td><td>0.0199 (6)</td><td>-0.0045 (6)</td><td>0.0062 (5)</td><td>-0.0078 (6)</td></tr><tr><td>B14</td><td>0.0279 (7)</td><td>0.0267 (8)</td><td>0.0165 (6)</td><td>0.0005 (6)</td><td>0.0069 (5)</td><td>-0.0023 (6)</td></tr><tr><td>B15</td><td>0.0301 (7)</td><td>0.0197 (7)</td><td>0.0195 (6)</td><td>-0.0017 (6)</td><td>0.0122 (6)</td><td>-0.0015 (6)</td></tr><tr><td>B16</td><td>0.0191 (6)</td><td>0.0245 (7)</td><td>0.0197 (6)</td><td>-0.0029 (5)</td><td>0.0076 (5)</td><td>-0.0064 (6)</td></tr><tr><td>B17</td><td>0.0201 (6)</td><td>0.0190 (7)</td><td>0.0196 (6)</td><td>0.0019 (5)</td><td>0.0058 (5)</td><td>-0.0003 (5)</td></tr><tr><td>B18</td><td>0.0190 (6)</td><td>0.0210 (7)</td><td>0.0188 (6)</td><td>-0.0029 (5)</td><td>0.0074 (5)</td><td>-0.0038 (5)</td></tr><tr><td>B19</td><td>0.0216 (6)</td><td>0.0238 (7)</td><td>0.0157 (6)</td><td>0.0035 (5)</td><td>0.0053 (5)</td><td>-0.0012 (5)</td></tr><tr><td>B20</td><td>0.0162 (5)</td><td>0.0168 (6)</td><td>0.0148 (6)</td><td>-0.0001 (5)</td><td>0.0050 (5)</td><td>-0.0017 (5)</td></tr></table>

Geometric parameters (Å, °)

<table><tr><td>N1—C6</td><td>1.3831 (15)</td><td>C33—C34</td><td>1.3875 (19)</td></tr><tr><td>N1—C9</td><td>1.4529 (15)</td><td>C33—H33</td><td>0.980 (17)</td></tr><tr><td>N1—C16</td><td>1.4536 (15)</td><td>C34—C35</td><td>1.377 (2)</td></tr><tr><td>N2—C28</td><td>1.3809 (15)</td><td>C34—H34</td><td>1.002 (19)</td></tr><tr><td>N2—C38</td><td>1.4525 (15)</td><td>C35—C36</td><td>1.3813 (19)</td></tr><tr><td>N2—C31</td><td>1.4533 (16)</td><td>C35—H35</td><td>0.990 (17)</td></tr><tr><td>C1—C2</td><td>1.6231 (18)</td><td>C36—C37</td><td>1.3903 (18)</td></tr><tr><td>C1—B2</td><td>1.687 (2)</td><td>C36—H36</td><td>0.959 (18)</td></tr><tr><td>C1—B3</td><td>1.690 (2)</td><td>C37—H37</td><td>0.957 (17)</td></tr><tr><td>C1—B1</td><td>1.711 (2)</td><td>C38—C39</td><td>1.5137 (17)</td></tr><tr><td>C1—B4</td><td>1.716 (2)</td><td>C38—H38A</td><td>1.025 (14)</td></tr><tr><td>C1—H1</td><td>0.968 (17)</td><td>C38—H38B</td><td>0.987 (16)</td></tr><tr><td>C2—B6</td><td>1.688 (2)</td><td>C39—C40</td><td>1.3893 (18)</td></tr><tr><td>C2—B5</td><td>1.695 (2)</td><td>C39—C44</td><td>1.3917 (17)</td></tr><tr><td>C2—B1</td><td>1.710 (2)</td><td>C40—C41</td><td>1.3899 (19)</td></tr><tr><td>C2—B4</td><td>1.722 (2)</td><td>C40—H40</td><td>1.007 (15)</td></tr><tr><td>C2—H2</td><td>0.957 (17)</td><td>C41—C42</td><td>1.384 (2)</td></tr><tr><td>C3—C8</td><td>1.3987 (15)</td><td>C41—H41</td><td>0.968 (18)</td></tr><tr><td>C3—C4</td><td>1.4026 (15)</td><td>C42—C43</td><td>1.377 (2)</td></tr><tr><td>C3—B10</td><td>1.5751 (17)</td><td>C42—H42</td><td>0.977 (19)</td></tr><tr><td>C4—C5</td><td>1.3851 (16)</td><td>C43—C44</td><td>1.392 (2)</td></tr><tr><td>C4—H4</td><td>0.999 (14)</td><td>C43—H43</td><td>0.984 (17)</td></tr><tr><td>C5—C6</td><td>1.4100 (16)</td><td>C44—H44</td><td>1.007 (17)</td></tr><tr><td>C5—H5</td><td>0.961 (15)</td><td>B1—B7</td><td>1.754 (2)</td></tr><tr><td>C6—C7</td><td>1.4078 (16)</td><td>B1—B2</td><td>1.767 (2)</td></tr><tr><td>C7—C8</td><td>1.3889 (16)</td><td>B1—B6</td><td>1.772 (2)</td></tr><tr><td>C7—H7</td><td>0.992 (14)</td><td>B1—H1X</td><td>1.074 (15)</td></tr><tr><td>C8—H8</td><td>1.004 (14)</td><td>B2—B8</td><td>1.769 (2)</td></tr><tr><td>C9—C10</td><td>1.5167 (17)</td><td>B2—B7</td><td>1.772 (2)</td></tr><tr><td>C9—H9A</td><td>0.998 (14)</td><td>B2—B3</td><td>1.773 (2)</td></tr><tr><td>C9—H9B</td><td>1.013 (16)</td><td>B2—H2X</td><td>1.072 (15)</td></tr><tr><td>C10—C11</td><td>1.3849 (18)</td><td>B3—B4</td><td>1.764 (2)</td></tr><tr><td>C10—C15</td><td>1.3915 (17)</td><td>B3—B8</td><td>1.767 (2)</td></tr><tr><td>C11—C12</td><td>1.3897 (19)</td><td>B3—B9</td><td>1.772 (2)</td></tr></table>
<table>
  <tr>
    <td>C11—H11</td>
    <td>0.976 (17)</td>
    <td>B3—H3X</td>
    <td>1.076 (16)</td>
  </tr>
  <tr>
    <td>C12—C13</td>
    <td>1.3818 (19)</td>
    <td>B4—B9</td>
    <td>1.761 (2)</td>
  </tr>
  <tr>
    <td>C12—H12</td>
    <td>0.951 (19)</td>
    <td>B4—B5</td>
    <td>1.778 (2)</td>
  </tr>
  <tr>
    <td>C13—C14</td>
    <td>1.378 (2)</td>
    <td>B4—H4X</td>
    <td>1.073 (17)</td>
  </tr>
  <tr>
    <td>C13—H13</td>
    <td>0.977 (17)</td>
    <td>B5—B6</td>
    <td>1.780 (2)</td>
  </tr>
  <tr>
    <td>C14—C15</td>
    <td>1.3870 (19)</td>
    <td>B5—B9</td>
    <td>1.781 (2)</td>
  </tr>
  <tr>
    <td>C14—H14</td>
    <td>1.00 (2)</td>
    <td>B5—B10</td>
    <td>1.783 (2)</td>
  </tr>
  <tr>
    <td>C15—H15</td>
    <td>0.983 (17)</td>
    <td>B5—H5X</td>
    <td>1.111 (15)</td>
  </tr>
  <tr>
    <td>C16—C17</td>
    <td>1.5133 (17)</td>
    <td>B6—B7</td>
    <td>1.770 (2)</td>
  </tr>
  <tr>
    <td>C16—H16A</td>
    <td>1.005 (14)</td>
    <td>B6—B10</td>
    <td>1.7893 (19)</td>
  </tr>
  <tr>
    <td>C16—H16B</td>
    <td>0.994 (16)</td>
    <td>B6—H6X</td>
    <td>1.077 (15)</td>
  </tr>
  <tr>
    <td>C17—C22</td>
    <td>1.3852 (18)</td>
    <td>B7—B8</td>
    <td>1.779 (2)</td>
  </tr>
  <tr>
    <td>C17—C18</td>
    <td>1.3888 (19)</td>
    <td>B7—B10</td>
    <td>1.811 (2)</td>
  </tr>
  <tr>
    <td>C18—C19</td>
    <td>1.389 (2)</td>
    <td>B7—H7X</td>
    <td>1.073 (15)</td>
  </tr>
  <tr>
    <td>C18—H18</td>
    <td>0.992 (16)</td>
    <td>B8—B9</td>
    <td>1.783 (2)</td>
  </tr>
  <tr>
    <td>C19—C20</td>
    <td>1.379 (2)</td>
    <td>B8—B10</td>
    <td>1.7837 (18)</td>
  </tr>
  <tr>
    <td>C19—H19</td>
    <td>0.951 (18)</td>
    <td>B8—H8X</td>
    <td>1.114 (14)</td>
  </tr>
  <tr>
    <td>C20—C21</td>
    <td>1.381 (3)</td>
    <td>B9—B10</td>
    <td>1.794 (2)</td>
  </tr>
  <tr>
    <td>C20—H20</td>
    <td>0.95 (2)</td>
    <td>B9—H9X</td>
    <td>1.118 (15)</td>
  </tr>
  <tr>
    <td>C21—C22</td>
    <td>1.394 (2)</td>
    <td>B11—B17</td>
    <td>1.764 (2)</td>
  </tr>
  <tr>
    <td>C21—H21</td>
    <td>1.03 (2)</td>
    <td>B11—B12</td>
    <td>1.770 (2)</td>
  </tr>
  <tr>
    <td>C22—H22</td>
    <td>1.024 (19)</td>
    <td>B11—B16</td>
    <td>1.774 (2)</td>
  </tr>
  <tr>
    <td>C23—C24</td>
    <td>1.6165 (18)</td>
    <td>B11—H11X</td>
    <td>1.097 (14)</td>
  </tr>
  <tr>
    <td>C23—B12</td>
    <td>1.688 (2)</td>
    <td>B12—B18</td>
    <td>1.771 (2)</td>
  </tr>
  <tr>
    <td>C23—B13</td>
    <td>1.6905 (19)</td>
    <td>B12—B13</td>
    <td>1.773 (2)</td>
  </tr>
  <tr>
    <td>C23—B14</td>
    <td>1.713 (2)</td>
    <td>B12—B17</td>
    <td>1.773 (2)</td>
  </tr>
  <tr>
    <td>C23—B11</td>
    <td>1.722 (2)</td>
    <td>B12—H12X</td>
    <td>1.082 (17)</td>
  </tr>
  <tr>
    <td>C23—H23</td>
    <td>0.971 (16)</td>
    <td>B13—B18</td>
    <td>1.769 (2)</td>
  </tr>
  <tr>
    <td>C24—B15</td>
    <td>1.690 (2)</td>
    <td>B13—B14</td>
    <td>1.770 (2)</td>
  </tr>
  <tr>
    <td>C24—B16</td>
    <td>1.6937 (19)</td>
    <td>B13—B19</td>
    <td>1.771 (2)</td>
  </tr>
  <tr>
    <td>C24—B11</td>
    <td>1.714 (2)</td>
    <td>B13—H13X</td>
    <td>1.075 (15)</td>
  </tr>
  <tr>
    <td>C24—B14</td>
    <td>1.7177 (19)</td>
    <td>B14—B19</td>
    <td>1.765 (2)</td>
  </tr>
  <tr>
    <td>C24—H24</td>
    <td>0.988 (15)</td>
    <td>B14—B15</td>
    <td>1.774 (2)</td>
  </tr>
  <tr>
    <td>C25—C26</td>
    <td>1.3988 (15)</td>
    <td>B14—H14X</td>
    <td>1.088 (15)</td>
  </tr>
  <tr>
    <td>C25—C30</td>
    <td>1.4011 (16)</td>
    <td>B15—B19</td>
    <td>1.781 (2)</td>
  </tr>
  <tr>
    <td>C25—B20</td>
    <td>1.5723 (17)</td>
    <td>B15—B16</td>
    <td>1.782 (2)</td>
  </tr>
  <tr>
    <td>C26—C27</td>
    <td>1.3873 (16)</td>
    <td>B15—B20</td>
    <td>1.794 (2)</td>
  </tr>
  <tr>
    <td>C26—H26</td>
    <td>0.969 (14)</td>
    <td>B15—H15X</td>
    <td>1.082 (15)</td>
  </tr>
  <tr>
    <td>C27—C28</td>
    <td>1.4074 (16)</td>
    <td>B16—B17</td>
    <td>1.770 (2)</td>
  </tr>
  <tr>
    <td>C27—H27</td>
    <td>0.966 (14)</td>
    <td>B16—B20</td>
    <td>1.7866 (19)</td>
  </tr>
  <tr>
    <td>C28—C29</td>
    <td>1.4074 (16)</td>
    <td>B16—H16X</td>
    <td>1.081 (15)</td>
  </tr>
  <tr>
    <td>C29—C30</td>
    <td>1.3878 (16)</td>
    <td>B17—B18</td>
    <td>1.7815 (19)</td>
  </tr>
  <tr>
    <td>C29—H29</td>
    <td>0.964 (15)</td>
    <td>B17—B20</td>
    <td>1.800 (2)</td>
  </tr>
  <tr>
    <td>C30—H30</td>
    <td>1.016 (14)</td>
    <td>B17—H17X</td>
    <td>1.130 (15)</td>
  </tr>
  <tr>
    <td>C31—C32</td>
    <td>1.5168 (17)</td>
    <td>B18—B19</td>
    <td>1.782 (2)</td>
  </tr>
  <tr>
    <td>C31—H31A</td>
    <td>1.017 (15)</td>
    <td>B18—B20</td>
    <td>1.7838 (19)</td>
  </tr>
  <tr>
    <td>C31—H31B</td>
    <td>0.985 (16)</td>
    <td>B18—H18X</td>
    <td>1.111 (15)</td>
  </tr>
  <tr>
    <td>C32—C37</td>
    <td>1.3867 (18)</td>
    <td>B19—B20</td>
    <td>1.7906 (19)</td>
  </tr>
</table>
<table><tr><td>C32—C33</td><td>1.3888 (17)</td><td>B19—H19X</td><td>1.109 (15)</td></tr><tr><td>C6—N1—C9</td><td>119.95 (10)</td><td>C1—B4—B5</td><td>103.63 (11)</td></tr><tr><td>C6—N1—C16</td><td>120.99 (10)</td><td>C2—B4—B5</td><td>57.90 (9)</td></tr><tr><td>C9—N1—C16</td><td>118.32 (10)</td><td>B9—B4—B5</td><td>60.42 (8)</td></tr><tr><td>C28—N2—C38</td><td>120.85 (10)</td><td>B3—B4—B5</td><td>108.02 (11)</td></tr><tr><td>C28—N2—C31</td><td>120.09 (10)</td><td>C1—B4—H4X</td><td>117.2 (9)</td></tr><tr><td>C38—N2—C31</td><td>118.89 (10)</td><td>C2—B4—H4X</td><td>116.8 (8)</td></tr><tr><td>C2—C1—B2</td><td>111.41 (11)</td><td>B9—B4—H4X</td><td>132.9 (8)</td></tr><tr><td>C2—C1—B3</td><td>111.34 (10)</td><td>B3—B4—H4X</td><td>125.3 (8)</td></tr><tr><td>B2—C1—B3</td><td>63.35 (9)</td><td>B5—B4—H4X</td><td>124.1 (9)</td></tr><tr><td>C2—C1—B1</td><td>61.64 (9)</td><td>C2—B5—B4</td><td>59.38 (9)</td></tr><tr><td>B2—C1—B1</td><td>62.64 (9)</td><td>C2—B5—B6</td><td>58.07 (9)</td></tr><tr><td>B3—C1—B1</td><td>115.29 (11)</td><td>B4—B5—B6</td><td>108.25 (11)</td></tr><tr><td>C2—C1—B4</td><td>62.01 (9)</td><td>C2—B5—B9</td><td>104.32 (10)</td></tr><tr><td>B2—C1—B4</td><td>115.32 (11)</td><td>B4—B5—B9</td><td>59.29 (9)</td></tr><tr><td>B3—C1—B4</td><td>62.38 (9)</td><td>B6—B5—B9</td><td>108.14 (10)</td></tr><tr><td>B1—C1—B4</td><td>115.66 (11)</td><td>C2—B5—B10</td><td>104.59 (11)</td></tr><tr><td>C2—C1—H1</td><td>116.0 (9)</td><td>B4—B5—B10</td><td>108.27 (10)</td></tr><tr><td>B2—C1—H1</td><td>122.4 (10)</td><td>B6—B5—B10</td><td>60.29 (8)</td></tr><tr><td>B3—C1—H1</td><td>121.7 (9)</td><td>B9—B5—B10</td><td>60.44 (8)</td></tr><tr><td>B1—C1—H1</td><td>116.0 (10)</td><td>C2—B5—H5X</td><td>116.8 (8)</td></tr><tr><td>B4—C1—H1</td><td>114.7 (10)</td><td>B4—B5—H5X</td><td>117.8 (8)</td></tr><tr><td>C1—C2—B6</td><td>111.71 (11)</td><td>B6—B5—H5X</td><td>119.1 (8)</td></tr><tr><td>C1—C2—B5</td><td>111.75 (10)</td><td>B9—B5—H5X</td><td>128.5 (8)</td></tr><tr><td>B6—C2—B5</td><td>63.48 (9)</td><td>B10—B5—H5X</td><td>128.9 (8)</td></tr><tr><td>C1—C2—B1</td><td>61.71 (9)</td><td>C2—B6—B7</td><td>104.38 (10)</td></tr><tr><td>B6—C2—B1</td><td>62.87 (9)</td><td>C2—B6—B1</td><td>59.16 (9)</td></tr><tr><td>B5—C2—B1</td><td>115.77 (11)</td><td>B7—B6—B1</td><td>59.35 (9)</td></tr><tr><td>C1—C2—B4</td><td>61.65 (9)</td><td>C2—B6—B5</td><td>58.45 (9)</td></tr><tr><td>B6—C2—B4</td><td>115.45 (10)</td><td>B7—B6—B5</td><td>108.64 (10)</td></tr><tr><td>B5—C2—B4</td><td>62.72 (9)</td><td>B1—B6—B5</td><td>108.56 (11)</td></tr><tr><td>B1—C2—B4</td><td>115.42 (10)</td><td>C2—B6—B10</td><td>104.59 (10)</td></tr><tr><td>C1—C2—H2</td><td>114.7 (10)</td><td>B7—B6—B10</td><td>61.17 (8)</td></tr><tr><td>B6—C2—H2</td><td>122.5 (10)</td><td>B1—B6—B10</td><td>108.78 (10)</td></tr><tr><td>B5—C2—H2</td><td>122.9 (10)</td><td>B5—B6—B10</td><td>59.94 (8)</td></tr><tr><td>B1—C2—H2</td><td>114.4 (10)</td><td>C2—B6—H6X</td><td>120.5 (8)</td></tr><tr><td>B4—C2—H2</td><td>115.4 (10)</td><td>B7—B6—H6X</td><td>125.3 (9)</td></tr><tr><td>C8—C3—C4</td><td>115.51 (10)</td><td>B1—B6—H6X</td><td>118.8 (8)</td></tr><tr><td>C8—C3—B10</td><td>122.41 (10)</td><td>B5—B6—H6X</td><td>120.5 (8)</td></tr><tr><td>C4—C3—B10</td><td>122.05 (10)</td><td>B10—B6—H6X</td><td>126.0 (8)</td></tr><tr><td>C5—C4—C3</td><td>122.67 (11)</td><td>B1—B7—B6</td><td>60.40 (9)</td></tr><tr><td>C5—C4—H4</td><td>117.1 (8)</td><td>B1—B7—B2</td><td>60.14 (9)</td></tr><tr><td>C3—C4—H4</td><td>120.3 (8)</td><td>B6—B7—B2</td><td>107.92 (11)</td></tr><tr><td>C4—C5—C6</td><td>121.14 (11)</td><td>B1—B7—B8</td><td>107.94 (11)</td></tr><tr><td>C4—C5—H5</td><td>120.0 (9)</td><td>B6—B7—B8</td><td>107.22 (11)</td></tr><tr><td>C6—C5—H5</td><td>118.8 (9)</td><td>B2—B7—B8</td><td>59.75 (8)</td></tr><tr><td>N1—C6—C7</td><td>122.21 (10)</td><td>B1—B7—B10</td><td>108.64 (11)</td></tr></table>
<table>
  <tr>
    <td>N1—C6—C5</td>
    <td>121.11 (11)</td>
  </tr>
  <tr>
    <td>C7—C6—C5</td>
    <td>116.68 (11)</td>
  </tr>
  <tr>
    <td>C8—C7—C6</td>
    <td>120.81 (10)</td>
  </tr>
  <tr>
    <td>C8—C7—H7</td>
    <td>117.5 (9)</td>
  </tr>
  <tr>
    <td>C6—C7—H7</td>
    <td>121.7 (9)</td>
  </tr>
  <tr>
    <td>C7—C8—C3</td>
    <td>122.97 (11)</td>
  </tr>
  <tr>
    <td>C7—C8—H8</td>
    <td>117.3 (8)</td>
  </tr>
  <tr>
    <td>C3—C8—H8</td>
    <td>119.7 (8)</td>
  </tr>
  <tr>
    <td>N1—C9—C10</td>
    <td>115.63 (10)</td>
  </tr>
  <tr>
    <td>N1—C9—H9A</td>
    <td>109.0 (8)</td>
  </tr>
  <tr>
    <td>C10—C9—H9A</td>
    <td>111.0 (8)</td>
  </tr>
  <tr>
    <td>N1—C9—H9B</td>
    <td>104.8 (8)</td>
  </tr>
  <tr>
    <td>C10—C9—H9B</td>
    <td>111.0 (9)</td>
  </tr>
  <tr>
    <td>H9A—C9—H9B</td>
    <td>104.7 (12)</td>
  </tr>
  <tr>
    <td>C11—C10—C15</td>
    <td>118.56 (12)</td>
  </tr>
  <tr>
    <td>C11—C10—C9</td>
    <td>122.37 (11)</td>
  </tr>
  <tr>
    <td>C15—C10—C9</td>
    <td>119.06 (11)</td>
  </tr>
  <tr>
    <td>C10—C11—C12</td>
    <td>120.60 (12)</td>
  </tr>
  <tr>
    <td>C10—C11—H11</td>
    <td>119.2 (10)</td>
  </tr>
  <tr>
    <td>C12—C11—H11</td>
    <td>120.2 (10)</td>
  </tr>
  <tr>
    <td>C13—C12—C11</td>
    <td>120.15 (13)</td>
  </tr>
  <tr>
    <td>C13—C12—H12</td>
    <td>120.3 (11)</td>
  </tr>
  <tr>
    <td>C11—C12—H12</td>
    <td>119.5 (11)</td>
  </tr>
  <tr>
    <td>C14—C13—C12</td>
    <td>119.87 (13)</td>
  </tr>
  <tr>
    <td>C14—C13—H13</td>
    <td>121.4 (9)</td>
  </tr>
  <tr>
    <td>C12—C13—H13</td>
    <td>118.7 (9)</td>
  </tr>
  <tr>
    <td>C13—C14—C15</td>
    <td>119.91 (13)</td>
  </tr>
  <tr>
    <td>C13—C14—H14</td>
    <td>120.3 (12)</td>
  </tr>
  <tr>
    <td>C15—C14—H14</td>
    <td>119.8 (12)</td>
  </tr>
  <tr>
    <td>C14—C15—C10</td>
    <td>120.90 (13)</td>
  </tr>
  <tr>
    <td>C14—C15—H15</td>
    <td>119.9 (10)</td>
  </tr>
  <tr>
    <td>C10—C15—H15</td>
    <td>119.2 (10)</td>
  </tr>
  <tr>
    <td>N1—C16—C17</td>
    <td>114.38 (10)</td>
  </tr>
  <tr>
    <td>N1—C16—H16A</td>
    <td>110.3 (8)</td>
  </tr>
  <tr>
    <td>C17—C16—H16A</td>
    <td>109.3 (8)</td>
  </tr>
  <tr>
    <td>N1—C16—H16B</td>
    <td>105.6 (8)</td>
  </tr>
  <tr>
    <td>C17—C16—H16B</td>
    <td>110.6 (9)</td>
  </tr>
  <tr>
    <td>H16A—C16—H16B</td>
    <td>106.3 (12)</td>
  </tr>
  <tr>
    <td>C22—C17—C18</td>
    <td>118.44 (13)</td>
  </tr>
  <tr>
    <td>C22—C17—C16</td>
    <td>120.78 (12)</td>
  </tr>
  <tr>
    <td>C18—C17—C16</td>
    <td>120.77 (11)</td>
  </tr>
  <tr>
    <td>C19—C18—C17</td>
    <td>120.81 (14)</td>
  </tr>
  <tr>
    <td>C19—C18—H18</td>
    <td>116.9 (10)</td>
  </tr>
  <tr>
    <td>C17—C18—H18</td>
    <td>122.3 (10)</td>
  </tr>
  <tr>
    <td>C20—C19—C18</td>
    <td>120.15 (15)</td>
  </tr>
  <tr>
    <td>C20—C19—H19</td>
    <td>120.3 (11)</td>
  </tr>
  <tr>
    <td>C18—C19—H19</td>
    <td>119.6 (11)</td>
  </tr>
  <tr>
    <td>C19—C20—C21</td>
    <td>119.86 (15)</td>
  </tr>
</table>

<table>
  <tr>
    <td>B6—B7—B10</td>
    <td>59.95 (8)</td>
  </tr>
  <tr>
    <td>B2—B7—B10</td>
    <td>107.82 (10)</td>
  </tr>
  <tr>
    <td>B8—B7—B10</td>
    <td>59.57 (7)</td>
  </tr>
  <tr>
    <td>B1—B7—H7X</td>
    <td>120.8 (8)</td>
  </tr>
  <tr>
    <td>B6—B7—H7X</td>
    <td>121.1 (8)</td>
  </tr>
  <tr>
    <td>B2—B7—H7X</td>
    <td>122.4 (8)</td>
  </tr>
  <tr>
    <td>B8—B7—H7X</td>
    <td>123.0 (8)</td>
  </tr>
  <tr>
    <td>B10—B7—H7X</td>
    <td>121.5 (8)</td>
  </tr>
  <tr>
    <td>B3—B8—B2</td>
    <td>60.19 (9)</td>
  </tr>
  <tr>
    <td>B3—B8—B7</td>
    <td>108.24 (10)</td>
  </tr>
  <tr>
    <td>B2—B8—B7</td>
    <td>59.92 (8)</td>
  </tr>
  <tr>
    <td>B3—B8—B9</td>
    <td>59.86 (9)</td>
  </tr>
  <tr>
    <td>B2—B8—B9</td>
    <td>108.44 (10)</td>
  </tr>
  <tr>
    <td>B7—B8—B9</td>
    <td>108.98 (10)</td>
  </tr>
  <tr>
    <td>B3—B8—B10</td>
    <td>108.59 (10)</td>
  </tr>
  <tr>
    <td>B2—B8—B10</td>
    <td>109.17 (9)</td>
  </tr>
  <tr>
    <td>B7—B8—B10</td>
    <td>61.10 (8)</td>
  </tr>
  <tr>
    <td>B9—B8—B10</td>
    <td>60.37 (8)</td>
  </tr>
  <tr>
    <td>B3—B8—H8X</td>
    <td>121.2 (7)</td>
  </tr>
  <tr>
    <td>B2—B8—H8X</td>
    <td>120.9 (7)</td>
  </tr>
  <tr>
    <td>B7—B8—H8X</td>
    <td>121.4 (7)</td>
  </tr>
  <tr>
    <td>B9—B8—H8X</td>
    <td>121.5 (7)</td>
  </tr>
  <tr>
    <td>B10—B8—H8X</td>
    <td>121.4 (7)</td>
  </tr>
  <tr>
    <td>B4—B9—B3</td>
    <td>59.91 (9)</td>
  </tr>
  <tr>
    <td>B4—B9—B5</td>
    <td>60.29 (9)</td>
  </tr>
  <tr>
    <td>B3—B9—B5</td>
    <td>107.57 (10)</td>
  </tr>
  <tr>
    <td>B4—B9—B8</td>
    <td>107.61 (10)</td>
  </tr>
  <tr>
    <td>B3—B9—B8</td>
    <td>59.62 (8)</td>
  </tr>
  <tr>
    <td>B5—B9—B8</td>
    <td>107.02 (10)</td>
  </tr>
  <tr>
    <td>B4—B9—B10</td>
    <td>108.59 (10)</td>
  </tr>
  <tr>
    <td>B3—B9—B10</td>
    <td>107.96 (10)</td>
  </tr>
  <tr>
    <td>B5—B9—B10</td>
    <td>59.84 (8)</td>
  </tr>
  <tr>
    <td>B8—B9—B10</td>
    <td>59.82 (8)</td>
  </tr>
  <tr>
    <td>B4—B9—H9X</td>
    <td>118.6 (8)</td>
  </tr>
  <tr>
    <td>B3—B9—H9X</td>
    <td>120.6 (8)</td>
  </tr>
  <tr>
    <td>B5—B9—H9X</td>
    <td>121.6 (7)</td>
  </tr>
  <tr>
    <td>B8—B9—H9X</td>
    <td>124.3 (8)</td>
  </tr>
  <tr>
    <td>B10—B9—H9X</td>
    <td>124.0 (8)</td>
  </tr>
  <tr>
    <td>C3—B10—B5</td>
    <td>121.91 (10)</td>
  </tr>
  <tr>
    <td>C3—B10—B8</td>
    <td>123.76 (10)</td>
  </tr>
  <tr>
    <td>B5—B10—B8</td>
    <td>106.91 (10)</td>
  </tr>
  <tr>
    <td>C3—B10—B6</td>
    <td>121.06 (10)</td>
  </tr>
  <tr>
    <td>B5—B10—B6</td>
    <td>59.77 (9)</td>
  </tr>
  <tr>
    <td>B8—B10—B6</td>
    <td>106.18 (9)</td>
  </tr>
  <tr>
    <td>C3—B10—B9</td>
    <td>123.34 (10)</td>
  </tr>
  <tr>
    <td>B5—B10—B9</td>
    <td>59.72 (8)</td>
  </tr>
  <tr>
    <td>B8—B10—B9</td>
    <td>59.81 (8)</td>
  </tr>
  <tr>
    <td>B6—B10—B9</td>
    <td>107.16 (10)</td>
  </tr>
</table>
C19—C20—H20
C21—C20—H20
C20—C21—C22
C20—C21—H21
C22—C21—H21
C17—C22—C21
C17—C22—H22
C21—C22—H22
C24—C23—B12
C24—C23—B13
B12—C23—B13
C24—C23—B14
B12—C23—B14
B13—C23—B14
C24—C23—B11
B12—C23—B11
B13—C23—B11
B14—C23—B11
C24—C23—H23
B12—C23—H23
B13—C23—H23
B14—C23—H23
B11—C23—H23
C23—C24—B15
C23—C24—B16
B15—C24—B16
C23—C24—B11
B15—C24—B11
B16—C24—B11
C23—C24—B14
B15—C24—B14
B16—C24—B14
B11—C24—B14
C23—C24—H24
B15—C24—H24
B16—C24—H24
B11—C24—H24
B14—C24—H24
C26—C25—C30
C26—C25—B20
C30—C25—B20
C27—C26—C25
C27—C26—H26
C25—C26—H26
C26—C27—C28
C26—C27—H27
C28—C27—H27
N2—C28—C27
120.3 (12)
119.8 (12)
119.78 (15)
120.5 (12)
119.7 (12)
120.96 (15)
119.6 (11)
119.4 (11)
111.31 (10)
111.54 (10)
63.30 (9)
62.04 (8)
115.49 (10)
62.67 (9)
61.69 (8)
62.56 (9)
115.38 (10)
115.88 (10)
116.5 (9)
121.2 (9)
122.1 (9)
116.0 (9)
114.7 (9)
111.86 (10)
111.84 (10)
63.56 (9)
62.17 (8)
116.04 (10)
62.75 (9)
61.73 (8)
62.72 (9)
115.56 (10)
116.02 (10)
115.6 (9)
122.0 (9)
121.8 (9)
114.5 (9)
115.5 (9)
115.45 (11)
122.01 (10)
122.50 (10)
123.06 (11)
117.3 (9)
119.7 (8)
120.74 (11)
118.1 (9)
121.1 (9)
121.73 (10)

C3—B10—B7
B5—B10—B7
B8—B10—B7
B6—B10—B7
B9—B10—B7
C24—B11—C23
C24—B11—B17
C23—B11—B17
C24—B11—B12
C23—B11—B12
B17—B11—B12
C24—B11—B16
C23—B11—B16
B17—B11—B16
B12—B11—B16
C24—B11—H11X
C23—B11—H11X
B17—B11—H11X
B12—B11—H11X
B16—B11—H11X
C23—B12—B11
C23—B12—B18
B11—B12—B18
C23—B12—B13
B11—B12—B13
B18—B12—B13
C23—B12—B17
B11—B12—B17
B18—B12—B17
B13—B12—B17
C23—B12—H12X
B11—B12—H12X
B18—B12—H12X
B13—B12—H12X
B17—B12—H12X
C23—B13—B18
C23—B13—B14
B18—B13—B14
C23—B13—B19
B18—B13—B19
B14—B13—B19
C23—B13—B12
B18—B13—B12
B14—B13—B12
B19—B13—B12
C23—B13—H13X
B18—B13—H13X
B14—B13—H13X
121.93 (11)
106.70 (10)
59.33 (8)
58.88 (8)
107.13 (9)
56.13 (8)
103.81 (10)
103.82 (10)
103.06 (10)
57.78 (8)
60.23 (8)
58.06 (8)
103.31 (10)
60.05 (8)
107.56 (10)
117.1 (8)
116.4 (8)
133.6 (8)
124.3 (8)
125.7 (8)
59.66 (8)
104.29 (11)
108.33 (10)
58.43 (8)
108.97 (11)
59.89 (8)
104.83 (10)
59.69 (8)
60.35 (8)
108.40 (11)
118.6 (9)
117.7 (8)
128.1 (8)
120.1 (9)
126.5 (9)
104.26 (10)
59.27 (8)
108.36 (10)
104.66 (10)
60.46 (8)
59.77 (9)
58.27 (8)
60.01 (8)
108.53 (10)
108.45 (10)
118.4 (8)
128.5 (8)
117.3 (8)
<table>
  <tr>
    <td>N2-C28-C29</td>
    <td>121.39 (11)</td>
  </tr>
  <tr>
    <td>C27-C28-C29</td>
    <td>116.88 (11)</td>
  </tr>
  <tr>
    <td>C30-C29-C28</td>
    <td>120.98 (11)</td>
  </tr>
  <tr>
    <td>C30-C29-H29</td>
    <td>120.8 (9)</td>
  </tr>
  <tr>
    <td>C28-C29-H29</td>
    <td>118.2 (9)</td>
  </tr>
  <tr>
    <td>C29-C30-C25</td>
    <td>122.75 (11)</td>
  </tr>
  <tr>
    <td>C29-C30-H30</td>
    <td>117.2 (8)</td>
  </tr>
  <tr>
    <td>C25-C30-H30</td>
    <td>120.0 (8)</td>
  </tr>
  <tr>
    <td>N2-C31-C32</td>
    <td>115.53 (10)</td>
  </tr>
  <tr>
    <td>N2-C31-H31A</td>
    <td>109.9 (9)</td>
  </tr>
  <tr>
    <td>C32-C31-H31A</td>
    <td>109.3 (9)</td>
  </tr>
  <tr>
    <td>N2-C31-H31B</td>
    <td>105.6 (8)</td>
  </tr>
  <tr>
    <td>C32-C31-H31B</td>
    <td>108.9 (9)</td>
  </tr>
  <tr>
    <td>H31A-C31-H31B</td>
    <td>107.2 (12)</td>
  </tr>
  <tr>
    <td>C37-C32-C33</td>
    <td>118.65 (12)</td>
  </tr>
  <tr>
    <td>C37-C32-C31</td>
    <td>122.31 (11)</td>
  </tr>
  <tr>
    <td>C33-C32-C31</td>
    <td>119.02 (11)</td>
  </tr>
  <tr>
    <td>C34-C33-C32</td>
    <td>120.78 (13)</td>
  </tr>
  <tr>
    <td>C34-C33-H33</td>
    <td>119.5 (10)</td>
  </tr>
  <tr>
    <td>C32-C33-H33</td>
    <td>119.7 (10)</td>
  </tr>
  <tr>
    <td>C35-C34-C33</td>
    <td>120.01 (13)</td>
  </tr>
  <tr>
    <td>C35-C34-H34</td>
    <td>120.4 (11)</td>
  </tr>
  <tr>
    <td>C33-C34-H34</td>
    <td>119.6 (11)</td>
  </tr>
  <tr>
    <td>C34-C35-C36</td>
    <td>119.92 (13)</td>
  </tr>
  <tr>
    <td>C34-C35-H35</td>
    <td>120.6 (9)</td>
  </tr>
  <tr>
    <td>C36-C35-H35</td>
    <td>119.5 (9)</td>
  </tr>
  <tr>
    <td>C35-C36-C37</td>
    <td>120.03 (13)</td>
  </tr>
  <tr>
    <td>C35-C36-H36</td>
    <td>121.9 (10)</td>
  </tr>
  <tr>
    <td>C37-C36-H36</td>
    <td>118.0 (10)</td>
  </tr>
  <tr>
    <td>C32-C37-C36</td>
    <td>120.59 (12)</td>
  </tr>
  <tr>
    <td>C32-C37-H37</td>
    <td>120.4 (11)</td>
  </tr>
  <tr>
    <td>C36-C37-H37</td>
    <td>119.0 (11)</td>
  </tr>
  <tr>
    <td>N2-C38-C39</td>
    <td>114.61 (10)</td>
  </tr>
  <tr>
    <td>N2-C38-H38A</td>
    <td>111.0 (8)</td>
  </tr>
  <tr>
    <td>C39-C38-H38A</td>
    <td>109.3 (8)</td>
  </tr>
  <tr>
    <td>N2-C38-H38B</td>
    <td>107.2 (8)</td>
  </tr>
  <tr>
    <td>C39-C38-H38B</td>
    <td>109.3 (9)</td>
  </tr>
  <tr>
    <td>H38A-C38-H38B</td>
    <td>104.8 (12)</td>
  </tr>
  <tr>
    <td>C40-C39-C44</td>
    <td>118.51 (12)</td>
  </tr>
  <tr>
    <td>C40-C39-C38</td>
    <td>120.39 (11)</td>
  </tr>
  <tr>
    <td>C44-C39-C38</td>
    <td>121.07 (12)</td>
  </tr>
  <tr>
    <td>C39-C40-C41</td>
    <td>120.96 (13)</td>
  </tr>
  <tr>
    <td>C39-C40-H40</td>
    <td>122.3 (9)</td>
  </tr>
  <tr>
    <td>C41-C40-H40</td>
    <td>116.7 (9)</td>
  </tr>
  <tr>
    <td>C42-C41-C40</td>
    <td>119.90 (14)</td>
  </tr>
  <tr>
    <td>C42-C41-H41</td>
    <td>122.1 (11)</td>
  </tr>
  <tr>
    <td>C40-C41-H41</td>
    <td>118.0 (11)</td>
  </tr>
  <tr>
    <td>C43-C42-C41</td>
    <td>119.77 (14)</td>
  </tr>
</table>

<table>
  <tr>
    <td>B19-B13-H13X</td>
    <td>126.4 (8)</td>
  </tr>
  <tr>
    <td>B12-B13-H13X</td>
    <td>120.4 (8)</td>
  </tr>
  <tr>
    <td>C23-B14-C24</td>
    <td>56.23 (8)</td>
  </tr>
  <tr>
    <td>C23-B14-B19</td>
    <td>104.03 (10)</td>
  </tr>
  <tr>
    <td>C24-B14-B19</td>
    <td>103.81 (10)</td>
  </tr>
  <tr>
    <td>C23-B14-B13</td>
    <td>58.05 (8)</td>
  </tr>
  <tr>
    <td>C24-B14-B13</td>
    <td>103.26 (10)</td>
  </tr>
  <tr>
    <td>B19-B14-B13</td>
    <td>60.16 (9)</td>
  </tr>
  <tr>
    <td>C23-B14-B15</td>
    <td>103.58 (10)</td>
  </tr>
  <tr>
    <td>C24-B14-B15</td>
    <td>57.88 (8)</td>
  </tr>
  <tr>
    <td>B19-B14-B15</td>
    <td>60.44 (8)</td>
  </tr>
  <tr>
    <td>B13-B14-B15</td>
    <td>108.00 (10)</td>
  </tr>
  <tr>
    <td>C23-B14-H14X</td>
    <td>118.4 (8)</td>
  </tr>
  <tr>
    <td>C24-B14-H14X</td>
    <td>117.7 (8)</td>
  </tr>
  <tr>
    <td>B19-B14-H14X</td>
    <td>131.9 (8)</td>
  </tr>
  <tr>
    <td>B13-B14-H14X</td>
    <td>125.5 (8)</td>
  </tr>
  <tr>
    <td>B15-B14-H14X</td>
    <td>123.5 (8)</td>
  </tr>
  <tr>
    <td>C24-B15-B14</td>
    <td>59.40 (8)</td>
  </tr>
  <tr>
    <td>C24-B15-B19</td>
    <td>104.26 (10)</td>
  </tr>
  <tr>
    <td>B14-B15-B19</td>
    <td>59.53 (8)</td>
  </tr>
  <tr>
    <td>C24-B15-B16</td>
    <td>58.31 (8)</td>
  </tr>
  <tr>
    <td>B14-B15-B16</td>
    <td>108.51 (11)</td>
  </tr>
  <tr>
    <td>B19-B15-B16</td>
    <td>107.76 (10)</td>
  </tr>
  <tr>
    <td>C24-B15-B20</td>
    <td>104.35 (10)</td>
  </tr>
  <tr>
    <td>B14-B15-B20</td>
    <td>108.23 (10)</td>
  </tr>
  <tr>
    <td>B19-B15-B20</td>
    <td>60.11 (8)</td>
  </tr>
  <tr>
    <td>B16-B15-B20</td>
    <td>59.94 (8)</td>
  </tr>
  <tr>
    <td>C24-B15-H15X</td>
    <td>118.4 (8)</td>
  </tr>
  <tr>
    <td>B14-B15-H15X</td>
    <td>119.3 (8)</td>
  </tr>
  <tr>
    <td>B19-B15-H15X</td>
    <td>128.2 (8)</td>
  </tr>
  <tr>
    <td>B16-B15-H15X</td>
    <td>118.8 (8)</td>
  </tr>
  <tr>
    <td>B20-B15-H15X</td>
    <td>127.2 (8)</td>
  </tr>
  <tr>
    <td>C24-B16-B17</td>
    <td>104.38 (10)</td>
  </tr>
  <tr>
    <td>C24-B16-B11</td>
    <td>59.19 (8)</td>
  </tr>
  <tr>
    <td>B17-B16-B11</td>
    <td>59.67 (8)</td>
  </tr>
  <tr>
    <td>C24-B16-B15</td>
    <td>58.12 (8)</td>
  </tr>
  <tr>
    <td>B17-B16-B15</td>
    <td>108.69 (10)</td>
  </tr>
  <tr>
    <td>B11-B16-B15</td>
    <td>108.57 (10)</td>
  </tr>
  <tr>
    <td>C24-B16-B20</td>
    <td>104.53 (9)</td>
  </tr>
  <tr>
    <td>B17-B16-B20</td>
    <td>60.81 (8)</td>
  </tr>
  <tr>
    <td>B11-B16-B20</td>
    <td>108.88 (10)</td>
  </tr>
  <tr>
    <td>B15-B16-B20</td>
    <td>60.36 (8)</td>
  </tr>
  <tr>
    <td>C24-B16-H16X</td>
    <td>118.1 (8)</td>
  </tr>
  <tr>
    <td>B17-B16-H16X</td>
    <td>127.1 (8)</td>
  </tr>
  <tr>
    <td>B11-B16-H16X</td>
    <td>117.5 (8)</td>
  </tr>
  <tr>
    <td>B15-B16-H16X</td>
    <td>119.7 (8)</td>
  </tr>
  <tr>
    <td>B20-B16-H16X</td>
    <td>128.1 (8)</td>
  </tr>
  <tr>
    <td>B11-B17-B16</td>
    <td>60.27 (8)</td>
  </tr>
</table>
<table>
  <tbody>
    <tr><td>C43-C42-H42</td><td>121.5 (10)</td></tr>
    <tr><td>C41-C42-H42</td><td>118.8 (10)</td></tr>
    <tr><td>C42-C43-C44</td><td>120.38 (14)</td></tr>
    <tr><td>C42-C43-H43</td><td>120.8 (10)</td></tr>
    <tr><td>C44-C43-H43</td><td>118.8 (10)</td></tr>
    <tr><td>C39-C44-C43</td><td>120.48 (14)</td></tr>
    <tr><td>C39-C44-H44</td><td>119.2 (10)</td></tr>
    <tr><td>C43-C44-H44</td><td>120.3 (10)</td></tr>
    <tr><td>C2-B1-C1</td><td>56.65 (8)</td></tr>
    <tr><td>C2-B1-B7</td><td>104.16 (10)</td></tr>
    <tr><td>C1-B1-B7</td><td>104.31 (10)</td></tr>
    <tr><td>C2-B1-B2</td><td>103.74 (11)</td></tr>
    <tr><td>C1-B1-B2</td><td>58.01 (9)</td></tr>
    <tr><td>B7-B1-B2</td><td>60.43 (9)</td></tr>
    <tr><td>C2-B1-B6</td><td>57.97 (9)</td></tr>
    <tr><td>C1-B1-B6</td><td>103.77 (11)</td></tr>
    <tr><td>B7-B1-B6</td><td>60.25 (8)</td></tr>
    <tr><td>B2-B1-B6</td><td>108.02 (10)</td></tr>
    <tr><td>C2-B1-H1X</td><td>118.5 (8)</td></tr>
    <tr><td>C1-B1-H1X</td><td>118.6 (9)</td></tr>
    <tr><td>B7-B1-H1X</td><td>130.9 (9)</td></tr>
    <tr><td>B2-B1-H1X</td><td>124.5 (8)</td></tr>
    <tr><td>B6-B1-H1X</td><td>124.1 (8)</td></tr>
    <tr><td>C1-B2-B1</td><td>59.35 (9)</td></tr>
    <tr><td>C1-B2-B8</td><td>104.12 (11)</td></tr>
    <tr><td>B1-B2-B8</td><td>107.84 (10)</td></tr>
    <tr><td>C1-B2-B7</td><td>104.55 (10)</td></tr>
    <tr><td>B1-B2-B7</td><td>59.42 (8)</td></tr>
    <tr><td>B8-B2-B7</td><td>60.34 (8)</td></tr>
    <tr><td>C1-B2-B3</td><td>58.40 (9)</td></tr>
    <tr><td>B1-B2-B3</td><td>108.50 (11)</td></tr>
    <tr><td>B8-B2-B3</td><td>59.87 (9)</td></tr>
    <tr><td>B7-B2-B3</td><td>108.32 (10)</td></tr>
    <tr><td>C1-B2-H2X</td><td>117.7 (8)</td></tr>
    <tr><td>B1-B2-H2X</td><td>118.4 (8)</td></tr>
    <tr><td>B8-B2-H2X</td><td>128.6 (8)</td></tr>
    <tr><td>B7-B2-H2X</td><td>127.9 (8)</td></tr>
    <tr><td>B3-B2-H2X</td><td>119.1 (8)</td></tr>
    <tr><td>C1-B3-B4</td><td>59.55 (9)</td></tr>
    <tr><td>C1-B3-B8</td><td>104.06 (10)</td></tr>
    <tr><td>B4-B3-B8</td><td>108.17 (10)</td></tr>
    <tr><td>C1-B3-B9</td><td>104.97 (10)</td></tr>
    <tr><td>B4-B3-B9</td><td>59.73 (9)</td></tr>
    <tr><td>B8-B3-B9</td><td>60.52 (8)</td></tr>
    <tr><td>C1-B3-B2</td><td>58.25 (9)</td></tr>
    <tr><td>B4-B3-B2</td><td>108.77 (11)</td></tr>
    <tr><td>B8-B3-B2</td><td>59.94 (9)</td></tr>
    <tr><td>B9-B3-B2</td><td>108.76 (10)</td></tr>
  </tbody>
</table>

<table>
  <tbody>
    <tr><td>B11-B17-B12</td><td>60.08 (8)</td></tr>
    <tr><td>B16-B17-B12</td><td>107.61 (10)</td></tr>
    <tr><td>B11-B17-B18</td><td>108.17 (10)</td></tr>
    <tr><td>B16-B17-B18</td><td>107.43 (10)</td></tr>
    <tr><td>B12-B17-B18</td><td>59.76 (8)</td></tr>
    <tr><td>B11-B17-B20</td><td>108.75 (10)</td></tr>
    <tr><td>B16-B17-B20</td><td>60.05 (8)</td></tr>
    <tr><td>B12-B17-B20</td><td>107.77 (10)</td></tr>
    <tr><td>B18-B17-B20</td><td>59.74 (8)</td></tr>
    <tr><td>B11-B17-H17X</td><td>119.9 (8)</td></tr>
    <tr><td>B16-B17-H17X</td><td>121.5 (8)</td></tr>
    <tr><td>B12-B17-H17X</td><td>121.7 (8)</td></tr>
    <tr><td>B18-B17-H17X</td><td>123.2 (7)</td></tr>
    <tr><td>B20-B17-H17X</td><td>122.5 (8)</td></tr>
    <tr><td>B13-B18-B12</td><td>60.10 (9)</td></tr>
    <tr><td>B13-B18-B17</td><td>108.20 (10)</td></tr>
    <tr><td>B12-B18-B17</td><td>59.89 (8)</td></tr>
    <tr><td>B13-B18-B19</td><td>59.84 (8)</td></tr>
    <tr><td>B12-B18-B19</td><td>108.04 (10)</td></tr>
    <tr><td>B17-B18-B19</td><td>108.53 (10)</td></tr>
    <tr><td>B13-B18-B20</td><td>108.45 (10)</td></tr>
    <tr><td>B12-B18-B20</td><td>108.60 (10)</td></tr>
    <tr><td>B17-B18-B20</td><td>60.65 (8)</td></tr>
    <tr><td>B19-B18-B20</td><td>60.28 (8)</td></tr>
    <tr><td>B13-B18-H18X</td><td>121.5 (8)</td></tr>
    <tr><td>B12-B18-H18X</td><td>120.8 (8)</td></tr>
    <tr><td>B17-B18-H18X</td><td>121.1 (8)</td></tr>
    <tr><td>B19-B18-H18X</td><td>122.4 (8)</td></tr>
    <tr><td>B20-B18-H18X</td><td>121.8 (8)</td></tr>
    <tr><td>B14-B19-B13</td><td>60.07 (9)</td></tr>
    <tr><td>B14-B19-B15</td><td>60.03 (8)</td></tr>
    <tr><td>B13-B19-B15</td><td>107.60 (10)</td></tr>
    <tr><td>B14-B19-B18</td><td>107.98 (10)</td></tr>
    <tr><td>B13-B19-B18</td><td>59.70 (8)</td></tr>
    <tr><td>B15-B19-B18</td><td>107.58 (10)</td></tr>
    <tr><td>B14-B19-B20</td><td>108.79 (10)</td></tr>
    <tr><td>B13-B19-B20</td><td>108.03 (10)</td></tr>
    <tr><td>B15-B19-B20</td><td>60.31 (8)</td></tr>
    <tr><td>B18-B19-B20</td><td>59.90 (8)</td></tr>
    <tr><td>B14-B19-H19X</td><td>120.2 (8)</td></tr>
    <tr><td>B13-B19-H19X</td><td>121.9 (8)</td></tr>
    <tr><td>B15-B19-H19X</td><td>121.2 (8)</td></tr>
    <tr><td>B18-B19-H19X</td><td>123.2 (8)</td></tr>
    <tr><td>B20-B19-H19X</td><td>122.0 (8)</td></tr>
    <tr><td>C25-B20-B18</td><td>124.41 (10)</td></tr>
    <tr><td>C25-B20-B16</td><td>120.92 (10)</td></tr>
    <tr><td>B18-B20-B16</td><td>106.62 (10)</td></tr>
    <tr><td>C25-B20-B19</td><td>122.50 (10)</td></tr>
  </tbody>
</table>
<table><caption>Hydrogen-bond geometry (Å, °)</caption><tr><td>C1—B3—H3X</td><td>118.2 (9)</td><td>B18—B20—B19</td><td>59.82 (8)</td></tr><tr><td>B4—B3—H3X</td><td>117.8 (9)</td><td>B16—B20—B19</td><td>107.14 (9)</td></tr><tr><td>B8—B3—H3X</td><td>128.5 (9)</td><td>C25—B20—B15</td><td>120.63 (10)</td></tr><tr><td>B9—B3—H3X</td><td>126.8 (9)</td><td>B18—B20—B15</td><td>106.94 (9)</td></tr><tr><td>B2—B3—H3X</td><td>119.6 (9)</td><td>B16—B20—B15</td><td>59.70 (8)</td></tr><tr><td>C1—B4—C2</td><td>56.34 (8)</td><td>B19—B20—B15</td><td>59.58 (8)</td></tr><tr><td>C1—B4—B9</td><td>104.33 (11)</td><td>C25—B20—B17</td><td>123.05 (10)</td></tr><tr><td>C2—B4—B9</td><td>104.06 (11)</td><td>B18—B20—B17</td><td>59.61 (8)</td></tr><tr><td>C1—B4—B3</td><td>58.07 (9)</td><td>B16—B20—B17</td><td>59.15 (8)</td></tr><tr><td>C2—B4—B3</td><td>103.42 (11)</td><td>B19—B20—B17</td><td>107.35 (10)</td></tr><tr><td>B9—B4—B3</td><td>60.36 (9)</td><td>B15—B20—B17</td><td>106.86 (10)</td></tr></table>

<table><thead><tr><th>D—H···A</th><th>D—H</th><th>H···A</th><th>D···A</th><th>D—H···A</th></tr></thead><tbody><tr><td>C1—H1···C3<sup>i</sup></td><td>0.968 (17)</td><td>2.742 (17)</td><td>3.6196 (17)</td><td>151.0 (13)</td></tr><tr><td>C1—H1···C4<sup>i</sup></td><td>0.968 (17)</td><td>2.676 (17)</td><td>3.5889 (17)</td><td>157.3 (12)</td></tr><tr><td>C1—H1···C5<sup>i</sup></td><td>0.968 (17)</td><td>2.740 (17)</td><td>3.6322 (18)</td><td>153.4 (12)</td></tr><tr><td>C1—H1···C6<sup>i</sup></td><td>0.968 (17)</td><td>2.860 (17)</td><td>3.7008 (18)</td><td>145.8 (13)</td></tr><tr><td>C1—H1···C7<sup>i</sup></td><td>0.968 (17)</td><td>2.797 (17)</td><td>3.6112 (18)</td><td>142.2 (12)</td></tr><tr><td>C1—H1···C8<sup>i</sup></td><td>0.968 (17)</td><td>2.745 (16)</td><td>3.5809 (18)</td><td>144.9 (12)</td></tr><tr><td>C23—H23···C25<sup>i</sup></td><td>0.971 (16)</td><td>2.780 (16)</td><td>3.6436 (17)</td><td>148.4 (12)</td></tr><tr><td>C23—H23···C26<sup>i</sup></td><td>0.971 (16)</td><td>2.741 (15)</td><td>3.5682 (17)</td><td>143.4 (11)</td></tr><tr><td>C23—H23···C27<sup>i</sup></td><td>0.971 (16)</td><td>2.724 (15)</td><td>3.5432 (18)</td><td>142.3 (11)</td></tr><tr><td>C23—H23···C28<sup>i</sup></td><td>0.971 (16)</td><td>2.749 (16)</td><td>3.6050 (18)</td><td>147.3 (12)</td></tr><tr><td>C23—H23···C29<sup>i</sup></td><td>0.971 (16)</td><td>2.681 (16)</td><td>3.5857 (18)</td><td>155.0 (12)</td></tr><tr><td>C23—H23···C30<sup>i</sup></td><td>0.971 (16)</td><td>2.690 (16)</td><td>3.5996 (17)</td><td>156.0 (12)</td></tr><tr><td>C16—H16B···C22<sup>ii</sup></td><td>0.994 (16)</td><td>2.869 (16)</td><td>3.769 (2)</td><td>151.0 (12)</td></tr><tr><td>C38—H38B···C44<sup>iii</sup></td><td>0.987 (16)</td><td>2.825 (16)</td><td>3.7325 (19)</td><td>153.3 (12)</td></tr></tbody></table>

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