# Synthesis and crystal structure of a new chiral alpha-aminooxime nickel(II) complex

Yasmina Homrani, Abdelaziz Dahdouh, Mohamed Amin El Mamrani, Pauline

Loxq, Frederic Capet, Isabelle Suisse, Mathieu Sauthier

► To cite this version:

Yasmina Homrani, Abdelaziz Dahdouh, Mohamed Amin El Mamrani, Pauline Loxq, Frederic Capet, et al.. Synthesis and crystal structure of a new chiral alpha-aminooxime nickel(II) complex. Acta crystallographica Section E: Crystallographic communications [2015-..], 2021, Acta crystallographica Section E: Crystallographic communications [2015-..], 77, 10.1107/S2056989021010537. hal-04125585

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Acta Cryst.

E

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN 2056-9890

Received 25 August 2021

Accepted 11 October 2021

Edited by J. Ellena, Universidade de São Paulo,
Brazil

**Keywords:** Nickel; α-aminooxime; (R)-limonene; crystal structure.

CCDC reference: 2115017

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

# Synthesis and crystal structure of a new chiral α-aminooxime nickel(II) complex

Yasmina Homrani,ª Abdelaziz Dahdouh,ª Mohamed Amin El Amrani,ª Pauline Loxq,ᵇ Frédéric Capet,ᵇ Isabelle Suisseᵇ and Mathieu Sauthierᵇ*

A dinuclear nickel complex with (S)-limonene based aminooxime ligand has been isolated and its crystal structure determined. The resolved structure of dichloridobis{(2S,5R)-2-methyl-5-(prop-1-en-2-yl)-2-[(pyridin-2-yl)methyl-amino]cyclohexan-1-one oxime}dinickel(II), [Ni₂Cl₂(C₁₆H₂₃ClN₃O₂)], at 100 K has monoclinic (P2₁) symmetry. The two Ni¹¹ ions in the dinuclear complex are each coordinated in a distorted octahedral environment by three nitrogen atoms, a terminal chloride and two μ bridging chlorides. Each oxime ligand is coordinated to nickel(II) by the three nitrogen atoms, leading to two five-membered chelate rings, each displaying an envelope conformation. In the crystal, numerous intermolecular and intramolecular hydrogen bonds lead to the formation of a three-dimensional network structure.

## 1. Chemical context

Asymmetric synthesis allows the preparation of enantiomerically enriched compounds either by using a chiral auxiliary, which will be temporarily introduced, or by using catalytic procedures (Gawley & Aubé, 2012). This latter method is particularly attractive as it contributes to the development of green chemistry, which maximizes efficiency and minimizes hazardous effects on human health and the environment (Anastas & Zimmerman, 2013). Thus, asymmetric catalysis avoids synthetic steps and only catalytic amounts of the optically pure auxiliary are needed (Ojima, 2010). As part of the development of this chemistry, the synthesis of new chiral organometallic complexes is always challenging. The pivotal point is then the synthesis of optically pure ligands, which will be coordinated to the metal center. In terms of sustainable chemistry, using the chiral pool to develop new ligands is most interesting (Elalami *et al.*, 2015). Coordination metal complexes containing terpenoid fragments are widely used in the pharmaceutical field and in catalysis. We have therefore developed ligands based on terpenes such as pinene and limonene (El Alami *et al.*, 2009, 2015; Chahboun *et al.*, 2012). In particular, the synthesis of optically pure aminooxime ligands has been performed successfully from (R)-limonene (El Alami *et al.*, 2012). These compounds possess structures with two or three nitrogen atoms as donor heteroatoms that could coordinate to the metal center. They have advantageously replaced phosphine ligands, which are generally unstable under air. Ruthenium (Benabdelouahab *et al.*, 2015) and palladium (de la Cueva-Alique *et al.*, 2019)

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OPEN

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ACCESS

<footnote>ªLaboratoire de Chimie Organique Appliquée, Faculté des Sciences, BP 2121, Université Abdelmalek Essaadi, Tétouan, Morocco, and ᵇUniv. Lille, CNRS, Centrale Lille, Univ. Artois, UMR 8181, UCCS, Unité de Catalyse et Chimie du Solide, F-59000, Lille, France. *Correspondence e-mail: mathieu.sauthier@univ-lille.fr</footnote>
complexes have already been synthesized with these ligands. Here we report the first synthesis of a limonene-based α-aminooxime nickel complex and its crystal structure. In the dinuclear title complex, each nickel ion is coordinated by (1S,4R)-1-picolylamino-p-menth-8-en-2-one oxime. The ligand was first synthesized from (R)-limonene through the addition of nitrosyl chloride, NOCl, to a picolylamine moiety, allowing the formation of the oxime moiety.

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## 2. Structural commentary

The title compound (Fig. 1) crystallizes in the monoclinic space group P2₁ with two chiral molecules per unit cell. The two Ni¹¹ ions in the dinuclear complex are each coordinated by three nitrogen atoms, a terminal chloride and two μ bridging chlorides. The environment around each metal center can then be described as a distorted octahedron with N1—Ni1—N2 and Cl1—Ni1—Cl3 angles of 79.91 (13) and 91.99 (4)°, respectively, together with Cl1—Ni1—N2 and Cl2—Ni1—N1 angles of 165.04 (11) and 88.69 (10)°, respectively. A similar arrangement can be found around the Ni2 atom [N4—Ni2—N5, Cl2—Ni2—Cl4, Cl4—Ni2—N5 and Cl4—Ni2—N4 = 79.7 (2), 99.38 (4), 166.04 (12) and 93.24 (16)°, respectively].

Each aminooxime ligand is coordinated to nickel(II) by the three nitrogen atoms, leading to two five-membered chelate rings, each displaying an envelope conformation (with N2 as the flap for Ni1/N1/C5/C6/N2 and N5 for Ni2/N4/C21/C22/N5). The six-membered carbocycles of the limonene units adopt a chair conformation. The lengths of the Ni1—N1, Ni1—N2 and Ni1—N3 bonds are 2.077 (3), 2.126 (4) and

<figure><img src="image_7.png" /><figcaption>**Figure 1**
Displacement ellipsoid plot at the 50% probability level for Ni₂(amino-oxime)₂Cl₄. H atoms are omitted for clarity.</figcaption></figure>

<table><caption>**Table 1**
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>O1—H1···Cl1</td><td>0.85 (7)</td><td>2.32 (6)</td><td>3.009 (4)</td><td>139 (6)</td></tr><tr><td>N2—H2···Cl4</td><td>0.77 (5)</td><td>2.46 (5)</td><td>3.209 (4)</td><td>166 (5)</td></tr><tr><td>O2—H2A···Cl4</td><td>0.76 (8)</td><td>2.31 (7)</td><td>2.978 (4)</td><td>147 (7)</td></tr><tr><td>C3—H3···O1<sup>i</sup></td><td>0.95</td><td>2.58</td><td>3.432 (5)</td><td>149</td></tr><tr><td>C1—H1A···Cl1</td><td>0.95</td><td>2.75</td><td>3.369 (5)</td><td>124</td></tr><tr><td>C6—H6A···Cl2</td><td>0.99</td><td>2.76</td><td>3.309 (5)</td><td>115</td></tr><tr><td>C11—H11B···Cl3<sup>ii</sup></td><td>0.99</td><td>2.64</td><td>3.573 (5)</td><td>156</td></tr><tr><td>C17—H17···Cl4</td><td>0.95</td><td>2.69</td><td>3.327 (6)</td><td>125</td></tr><tr><td>C26—H26···O2<sup>iii</sup></td><td>1.00</td><td>2.56</td><td>3.489 (6)</td><td>154</td></tr><tr><td>C22—H22B···Cl2</td><td>0.99</td><td>2.81</td><td>3.352 (6)</td><td>115</td></tr><tr><td>C19—H19···Cl1<sup>iv</sup></td><td>0.95</td><td>2.64</td><td>3.570 (7)</td><td>167</td></tr></tbody></table>

Symmetry codes: (i) $-x + 2, y - \frac{1}{2}, -z + 1$; (ii) $-x + 1, y - \frac{1}{2}, -z + 1$; (iii) $-x, y + \frac{1}{2}, -z$; (iv) $-x + 1, y - \frac{1}{2}, -z$.

2.041 (3) Å, respectively, while Ni2—N4, Ni2—N5 and Ni2—N6 are 2.095 (4), 2.103 (4) and 2.027 (3) Å. Atoms Cl1 and Cl4 are in a *trans*-position at distances of 2.4408 (12) and 2.4077 (14) Å from the metal centers Ni1 and Ni2, respectively. The two metal centers are linked by two bridging Cl atoms with an average Ni—Cl distance of 2.42 Å, which is normal for these bond lengths. All these values compare well with literature values. The two nickel ions are separated by a distance of 3.5198 (7) Å, which is similar to average values (Zheng *et al.*, 2010; Cheng *et al.*, 2012).

## 3. Supramolecular features

The crystal structure is stabilized by numerous intermolecular and intramolecular hydrogen bonds (Table 1), which link the component into a three-dimensional network (Figs. 2 and 3).

<figure><img src="image_8.png" /><figcaption>**Figure 2**
Intermolecular and intramolecular hydrogen bonds in the structure, shown as dashed lines.</figcaption></figure>
<figure><img src="image_9.png" /><figcaption>Figure 3
Packing diagram.</figcaption></figure>

In particular, the two {Ni(aminoxime)μ-Cl}Cl units are slightly asymmetrical with the existence of a hydrogen-bonding interaction between the amine N2–H2 linked to Ni1 and the chlorine atom Cl4 linked to Ni2. In addition, the two oxygen atoms O1 and O2 of the oxime groups are involved in intramolecular O1–H1···Cl1 and O2–H2A···Cl4 hydrogen bonds and in intermolecular C3–H3···O1 and C26–H26···O2 interactions.

## 4. Database survey

The aminoxime ligand used in this study was previously reacted with palladium and platinum precursors, generating three N-coordinated cationic complexes as enantiopure compounds (de la Cueva-Alique *et al.*, 2019). A heteronuclear TiIV/PdII complex has also been described. The compounds were studied to assess their potential biological activity, a high anticancer activity (de la Cueva-Alique *et al.*, 2019).

## 5. Synthesis and crystallization

To a solution of NiII chloride ethylene glycol dimethyl ether (0.15 g, 1.48 mmol) in MeOH (5 mL) was added (1S,4R)-1-picolylamino-p-menth-8-en-2-one-oxime (0.101 g, 0.36 mmol) dissolved in MeOH (3 mL). The solution turned green. The mixture was stirred overnight at room temperature during which time the mixture changed color to blue-green. The

<table><caption>Table 2
Experimental details.</caption><tr><td>Crystal data</td><td></td></tr><tr><td>Chemical formula</td><td>[Ni<sub>2</sub>Cl<sub>2</sub>(C<sub>16</sub>H<sub>23</sub>ClN<sub>3</sub>O)<sub>2</sub>]</td></tr><tr><td>M<sub>r</sub></td><td>805.97</td></tr><tr><td>Crystal system, space group</td><td>Monoclinic, P2<sub>1</sub></td></tr><tr><td>Temperature (K)</td><td>100</td></tr><tr><td>a, b, c (Å)</td><td>13.3729 (9), 8.9363 (7),<br/>16.4248 (16)</td></tr><tr><td>β (°)</td><td>114.014 (2)</td></tr><tr><td>V (Å<sup>3</sup>)</td><td>1792.9 (3)</td></tr><tr><td>Z</td><td>2</td></tr><tr><td>Radiation type</td><td>Mo Kα</td></tr><tr><td>μ (mm<sup>-1</sup>)</td><td>1.39</td></tr><tr><td>Crystal size (mm)</td><td>0.21 × 0.17 × 0.12</td></tr><tr><td>Data collection</td><td></td></tr><tr><td>Diffractometer</td><td>Bruker APEXII CCD</td></tr><tr><td>Absorption correction</td><td>Multi-scan (SADABS; Krause et al., 2015)</td></tr><tr><td>T<sub>min</sub>, T<sub>max</sub></td><td>0.669, 0.746</td></tr><tr><td>No. of measured, independent and<br/>observed [I > 2σ(I)] reflections</td><td>42747, 10769, 9436</td></tr><tr><td>R<sub>int</sub></td><td>0.037</td></tr><tr><td>(sin θ/λ)<sub>max</sub> (Å<sup>-1</sup>)</td><td>0.714</td></tr><tr><td>Refinement</td><td></td></tr><tr><td>R[F<sup>2</sup> > 2σ(F<sup>2</sup>)], wR(F<sup>2</sup>), S</td><td>0.043, 0.109, 1.05</td></tr><tr><td>No. of reflections</td><td>10769</td></tr><tr><td>No. of parameters</td><td>431</td></tr><tr><td>No. of restraints</td><td>13</td></tr><tr><td>H-atom treatment</td><td>H atoms treated by a mixture of<br/>independent and constrained<br/>refinement</td></tr><tr><td>Δρ<sub>max</sub>, Δρ<sub>min</sub> (e Å<sup>-3</sup>)</td><td>1.50, -1.19</td></tr><tr><td>Absolute structure</td><td>Flack x determined using 3850<br/>quotients [(I<sup>+</sup>)-(I<sup>-</sup>)]/[(I<sup>+</sup>)+(I<sup>-</sup>)]<br/>(Parsons et al., 2013)</td></tr><tr><td>Absolute structure parameter</td><td>-0.009 (4)</td></tr></table>

Computer programs: *APEX2* and *SAINT* (Bruker, 2019), *SHELXT* (Sheldrick, 2015a), *SHELXL* (Sheldrick, 2015b) and *OLEX2* (Dolomanov *et al.*, 2009).

solvent was then evaporated to produce a crude solid that was washed with diethyl ether before crystallization. Single crystals were grown by slow diffusion at room temperature of diethyl ether into a dichloromethane solution. Elemental analysis calculated for C<sub>32</sub>H<sub>46</sub>Cl<sub>4</sub>N<sub>6</sub>Ni<sub>2</sub>O<sub>2</sub>: C, 46.33; H, 5.54; N, 9.65. Found: C, 46.35; H, 5.672; N, 9.77.

## 6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. N- and O-bound atoms were refined with the restraint *U*<sub>iso</sub>(H) = 1.2*U*<sub>eq</sub>(N) or 1.5*U*<sub>eq</sub>(O). H atoms were positioned geometrically (C–H = 0.95–1.00 Å) and refined as riding with *U*<sub>iso</sub>(H) = 1.2*U*<sub>eq</sub>(C) or 1.5*U*<sub>eq</sub>(C-methyl)

## Acknowledgements

We would like to thank Céline Delabre for the elemental analysis.
## Funding information

The authors thank the Ministère de l'Enseignement Supérieur de la Recherche et de l'Innovation (France) and the Ministère de la Recherche (Morocco) for financial support. The Chevrel Institute (FR 2638), Ministry of Higher Education, Research and Innovation, Région Hauts de France and FEDER are recognized for funding of X-ray diffractometers.

## References

* Anastas, P. T. & Zimmerman, J. B. (2013). *Environ. Sci. Technol.* **37**, 95A–101A.

* Benabdelouahab, Y., Muñoz-Moreno, L., Frik, M., de la Cueva-Alique, I., El Amrani, M. A., Contel, M., Bajo, A. M., Cuenca, T. & Royo, E. (2015). *Eur. J. Inorg. Chem.* pp. 2295–2307.

* Bruker (2019). *APEX2* and *SAINT*. Bruker AXS Inc., Madison Wisconsin, USA.

* Chahboun, G., Brito, J. A., Royo, B., El Amrani, M. A., Gómez-Bengoa, E., Mosquera, M. E. G., Cuenca, T. & Royo, E. (2012). *Eur. J. Inorg. Chem.* pp. 2940–2949.

* Cheng, T.-P., Liao, B.-S., Liu, Y.-H., Peng, S.-M. & Liu, S.-T. (2012). *Dalton Trans.* **41**, 3468–3473.

* Cueva-Alique, I. de la, Muñoz-Moreno, L., de la Torre-Rubio, E., Bajo, A. M., Gude, L., Cuenca, T. & Royo, E. (2019). *Dalton Trans.* **48**, 14279–14293.

* Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). *J. Appl. Cryst.* **42**, 339–341.

* Elalami, M. S., Dahdouh, A. A., Mansour, A. I., El Amrani, M. A., Suisse, I., Mortreux, A. & Agbossou-Niedercorn, F. (2009). *C. R. Chim.* **12**, 1253–1258.

* El Alami, M. S. I., El Amrani, M. A., Agbossou-Niedercorn, F., Suisse, I. & Mortreux, A. (2015). *Chem. Eur. J.* **21**, 1398–1413.

* Gawley, R. E. & Aubé, J. (2012). *Principles and applications of asymmetric synthesis*, 2nd ed. Amsterdam: Elsevier Science

* El Alami, M. S. I., El Amrani, M. A., Dahdouh, A., Roussel, P., Suisse, I. & Mortreux, A. (2012). *Chirality*, **24**, 675–682.

* Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). *J. Appl. Cryst.* **48**, 3–10.

* Ojima, I. (2010). *Catalytic asymmetric synthesis*, 3rd ed. Hoboken: Wiley

* Parsons, S., Flack, H. D. & Wagner, T. (2013). *Acta Cryst.* **B69**, 249–259.

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

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

* Zheng, L., Zhang, S., Li, K., Chen, W., Chen, Y., Xu, B., Hu, B., Li, Y. & Li, W. (2010). *J. Mol. Struct.* **984**, 153–156.
supporting information

Acta Cryst. (2021). E77, 1116-1119 [https://doi.org/10.1107/S2056989021010537]

# Synthesis and crystal structure of a new chiral α-aminooxime nickel(II) complex

Yasmina Homrani, Abdelaziz Dahdouh, Mohamed Amin El Amrani, Pauline Loxq, Frédéric Capet, Isabelle Suisse and Mathieu Sauthier

## Computing details

Data collection: *APEX2* (Bruker, 2019); cell refinement: *SAINT* (Bruker, 2019); data reduction: *SAINT* (Bruker, 2019); program(s) used to solve structure: *ShelXT* (Sheldrick, 2015a); program(s) used to refine structure: *SHELXL* (Sheldrick, 2015b); molecular graphics: *OLEX2* (Dolomanov *et al.*, 2009); software used to prepare material for publication: *OLEX2* (Dolomanov *et al.*, 2009).

## Dichloridobis((2S,5R)-2-methyl-5-(prop-1-en-2-yl)-2-[(pyridin-2-yl)methylamino]cyclohexan-1-one oxime) dinickel(II)

### Crystal data

[Ni₂Cl₂(C₁₆H₂₃ClN₃O₂)]

$M_r = 805.97$

Monoclinic, *P2₁*

*a* = 13.3729 (9) Å

*b* = 8.9363 (7) Å

*c* = 16.4248 (16) Å

$\beta$ = 114.014 (2)°

$V = 1792.9 (3) Å³$

$Z = 2$

$F(000) = 840$

$D_x = 1.493 \text{ Mg m}^{-3}$

Mo Kα radiation, $\lambda = 0.71073$ Å

Cell parameters from 9996 reflections

$\theta = 2.7-30.0°$

$\mu = 1.39 \text{ mm}^{-1}$

$T = 100$ K

Block, green

0.21 × 0.17 × 0.12 mm

### Data collection

Bruker APEXII CCD
diffractometer

Radiation source: microfocus sealed X-ray tube

$\varphi$ and $\omega$ scans

Absorption correction: multi-scan
(SADABS; Krause *et al.*, 2015)

$T_{\text{min}} = 0.669, T_{\text{max}} = 0.746$

42747 measured reflections

10769 independent reflections

9436 reflections with *I* > 2σ(*I*)

$R_{\text{int}} = 0.037$

$\theta_{\text{max}} = 30.5°, \theta_{\text{min}} = 1.4°$

$h = -17 \rightarrow 19$

$k = -12 \rightarrow 12$

$l = -23 \rightarrow 21$

### Refinement

Refinement on *F*²

Least-squares matrix: full

$R[F^2 > 2\sigma(F^2)] = 0.043$

$wR(F^2) = 0.109$

$S = 1.05$

10769 reflections

431 parameters

13 restraints

Primary atom site location: dual

Secondary atom site location: difference Fourier
map

Hydrogen site location: mixed

H atoms treated by a mixture of independent
and constrained refinement

$w = 1/[\sigma^2(F_o^2) + (0.0581P)^2 + 0.9636P]$ where $P = (F_o^2 + 2F_c^2)/3$

($\Delta/\sigma)_{\text{max}} = 0.001$

$\Delta\rho_{\text{max}} = 1.50 \text{ e Å}^{-3}$
$$ \Delta\rho_{\min} = -1.18 \text{ e Å}^{-3} $$

Absolute structure: Flack *x* determined using 3850 quotients [(I')-(I)]/[(I')+(I)] (Parsons *et al.*, 2013)

Absolute structure parameter: -0.009 (4)

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>Ni1</td><td>0.66455 (4)</td><td>0.50226 (6)</td><td>0.35327 (3)</td><td>0.01526 (11)</td></tr><tr><td>Ni2</td><td>0.41917 (4)</td><td>0.48960 (6)</td><td>0.15985 (3)</td><td>0.01813 (12)</td></tr><tr><td>Cl2</td><td>0.61155 (8)</td><td>0.45928 (14)</td><td>0.19208 (7)</td><td>0.0259 (2)</td></tr><tr><td>Cl3</td><td>0.48342 (7)</td><td>0.60270 (12)</td><td>0.30567 (7)</td><td>0.0212 (2)</td></tr><tr><td>Cl1</td><td>0.74487 (8)</td><td>0.75170 (12)</td><td>0.37010 (7)</td><td>0.0249 (2)</td></tr><tr><td>Cl4</td><td>0.38501 (9)</td><td>0.25191 (13)</td><td>0.21270 (9)</td><td>0.0336 (3)</td></tr><tr><td>O1</td><td>0.7388 (3)</td><td>0.6301 (4)</td><td>0.5389 (2)</td><td>0.0244 (7)</td></tr><tr><td>H1</td><td>0.740 (5)</td><td>0.705 (7)</td><td>0.507 (4)</td><td>0.037*</td></tr><tr><td>N1</td><td>0.8111 (3)</td><td>0.3926 (4)</td><td>0.3786 (2)</td><td>0.0182 (7)</td></tr><tr><td>N3</td><td>0.6939 (2)</td><td>0.5043 (5)</td><td>0.4853 (2)</td><td>0.0183 (6)</td></tr><tr><td>N2</td><td>0.6216 (3)</td><td>0.2811 (4)</td><td>0.3745 (2)</td><td>0.0183 (7)</td></tr><tr><td>H2</td><td>0.563 (4)</td><td>0.289 (6)</td><td>0.339 (3)</td><td>0.022*</td></tr><tr><td>O2</td><td>0.1908 (3)</td><td>0.4533 (5)</td><td>0.1497 (2)</td><td>0.0339 (9)</td></tr><tr><td>H2A</td><td>0.226 (6)</td><td>0.389 (9)</td><td>0.176 (5)</td><td>0.051*</td></tr><tr><td>C8</td><td>0.6846 (3)</td><td>0.3877 (5)</td><td>0.5258 (3)</td><td>0.0203 (8)</td></tr><tr><td>C5</td><td>0.8008 (3)</td><td>0.2431 (5)</td><td>0.3699 (3)</td><td>0.0202 (8)</td></tr><tr><td>N6</td><td>0.2619 (3)</td><td>0.5471 (4)</td><td>0.1318 (2)</td><td>0.0212 (8)</td></tr><tr><td>N5</td><td>0.4081 (3)</td><td>0.6943 (5)</td><td>0.0936 (3)</td><td>0.0394 (12)</td></tr><tr><td>H5</td><td>0.468 (5)</td><td>0.736 (8)</td><td>0.140 (4)</td><td>0.047*</td></tr><tr><td>C12</td><td>0.7001 (3)</td><td>0.1123 (6)</td><td>0.5107 (3)</td><td>0.0250 (9)</td></tr><tr><td>H12A</td><td>0.660298</td><td>0.022653</td><td>0.478112</td><td>0.030*</td></tr><tr><td>H12B</td><td>0.770464</td><td>0.117488</td><td>0.504159</td><td>0.030*</td></tr><tr><td>C14</td><td>0.9033 (3)</td><td>0.2356 (6)</td><td>0.6758 (3)</td><td>0.0257 (9)</td></tr><tr><td>C3</td><td>0.9925 (4)</td><td>0.2136 (6)</td><td>0.4131 (3)</td><td>0.0301 (11)</td></tr><tr><td>H3</td><td>1.054899</td><td>0.151943</td><td>0.425362</td><td>0.036*</td></tr><tr><td>C9</td><td>0.7192 (4)</td><td>0.3765 (6)</td><td>0.6253 (3)</td><td>0.0279 (10)</td></tr><tr><td>H9A</td><td>0.653362</td><td>0.378843</td><td>0.638523</td><td>0.034*</td></tr><tr><td>H9B</td><td>0.764996</td><td>0.464264</td><td>0.654444</td><td>0.034*</td></tr><tr><td>C1</td><td>0.9109 (3)</td><td>0.4531 (5)</td><td>0.4044 (3)</td><td>0.0220 (9)</td></tr><tr><td>H1A</td><td>0.918464</td><td>0.558677</td><td>0.410777</td><td>0.026*</td></tr><tr><td>C30</td><td>0.0369 (4)</td><td>0.6416 (7)</td><td>-0.1114 (4)</td><td>0.0357 (12)</td></tr><tr><td>N4</td><td>0.3669 (3)</td><td>0.4143 (6)</td><td>0.0282 (3)</td><td>0.0361 (11)</td></tr><tr><td>C2</td><td>1.0041 (3)</td><td>0.3660 (6)</td><td>0.4222 (3)</td><td>0.0277 (10)</td></tr><tr><td>H2B</td><td>1.074096</td><td>0.411370</td><td>0.440161</td><td>0.033*</td></tr><tr><td>C25</td><td>0.1029 (4)</td><td>0.7072 (7)</td><td>0.0546 (4)</td><td>0.0384 (13)</td></tr></tbody></table>
<table>
  <tr>
    <td>H25A</td>
    <td>0.095090</td>
    <td>0.786671</td>
    <td>0.093629</td>
    <td>0.046*</td>
  </tr>
  <tr>
    <td>H25B</td>
    <td>0.059972</td>
    <td>0.619493</td>
    <td>0.058673</td>
    <td>0.046*</td>
  </tr>
  <tr>
    <td>C7</td>
    <td>0.6314 (3)</td>
    <td>0.2540 (5)</td>
    <td>0.4678 (3)</td>
    <td>0.0206 (8)</td>
  </tr>
  <tr>
    <td>C4</td>
    <td>0.8897 (4)</td>
    <td>0.1499 (6)</td>
    <td>0.3860 (3)</td>
    <td>0.0278 (10)</td>
  </tr>
  <tr>
    <td>H4</td>
    <td>0.880183</td>
    <td>0.044699</td>
    <td>0.378533</td>
    <td>0.033*</td>
  </tr>
  <tr>
    <td>C24</td>
    <td>0.2208 (4)</td>
    <td>0.6641 (5)</td>
    <td>0.0869 (3)</td>
    <td>0.0258 (10)</td>
  </tr>
  <tr>
    <td>C6</td>
    <td>0.6855 (3)</td>
    <td>0.1848 (5)</td>
    <td>0.3402 (3)</td>
    <td>0.0218 (8)</td>
  </tr>
  <tr>
    <td>H6A</td>
    <td>0.649955</td>
    <td>0.182503</td>
    <td>0.274260</td>
    <td>0.026*</td>
  </tr>
  <tr>
    <td>H6B</td>
    <td>0.687313</td>
    <td>0.081400</td>
    <td>0.362311</td>
    <td>0.026*</td>
  </tr>
  <tr>
    <td>C10</td>
    <td>0.7844 (4)</td>
    <td>0.2319 (6)</td>
    <td>0.6644 (3)</td>
    <td>0.0281 (10)</td>
  </tr>
  <tr>
    <td>H10</td>
    <td>0.785669</td>
    <td>0.219265</td>
    <td>0.725250</td>
    <td>0.034*</td>
  </tr>
  <tr>
    <td>C23</td>
    <td>0.2999 (4)</td>
    <td>0.7724 (5)</td>
    <td>0.0732 (4)</td>
    <td>0.0365 (12)</td>
  </tr>
  <tr>
    <td>C15</td>
    <td>0.9419 (4)</td>
    <td>0.3220 (6)</td>
    <td>0.6296 (3)</td>
    <td>0.0301 (10)</td>
  </tr>
  <tr>
    <td>H15A</td>
    <td>1.016603</td>
    <td>0.314817</td>
    <td>0.638711</td>
    <td>0.036*</td>
  </tr>
  <tr>
    <td>H15B</td>
    <td>0.894916</td>
    <td>0.391186</td>
    <td>0.587469</td>
    <td>0.036*</td>
  </tr>
  <tr>
    <td>C31</td>
    <td>0.0663 (3)</td>
    <td>0.5006 (7)</td>
    <td>-0.0931 (3)</td>
    <td>0.0322 (10)</td>
  </tr>
  <tr>
    <td>H31A</td>
    <td>0.053020</td>
    <td>0.430999</td>
    <td>-0.140077</td>
    <td>0.039*</td>
  </tr>
  <tr>
    <td>H31B</td>
    <td>0.100801</td>
    <td>0.468485</td>
    <td>-0.032826</td>
    <td>0.039*</td>
  </tr>
  <tr>
    <td>C13</td>
    <td>0.5139 (3)</td>
    <td>0.2394 (7)</td>
    <td>0.4628 (3)</td>
    <td>0.0314 (11)</td>
  </tr>
  <tr>
    <td>H13A</td>
    <td>0.471161</td>
    <td>0.327732</td>
    <td>0.433110</td>
    <td>0.047*</td>
  </tr>
  <tr>
    <td>H13B</td>
    <td>0.516636</td>
    <td>0.231714</td>
    <td>0.523147</td>
    <td>0.047*</td>
  </tr>
  <tr>
    <td>H13C</td>
    <td>0.479378</td>
    <td>0.149469</td>
    <td>0.428806</td>
    <td>0.047*</td>
  </tr>
  <tr>
    <td>C11</td>
    <td>0.7236 (4)</td>
    <td>0.0951 (6)</td>
    <td>0.6094 (3)</td>
    <td>0.0306 (11)</td>
  </tr>
  <tr>
    <td>H11A</td>
    <td>0.768517</td>
    <td>0.004325</td>
    <td>0.633040</td>
    <td>0.037*</td>
  </tr>
  <tr>
    <td>H11B</td>
    <td>0.653697</td>
    <td>0.081821</td>
    <td>0.615749</td>
    <td>0.037*</td>
  </tr>
  <tr>
    <td>C16</td>
    <td>0.9776 (4)</td>
    <td>0.1259 (6)</td>
    <td>0.7427 (3)</td>
    <td>0.0313 (11)</td>
  </tr>
  <tr>
    <td>H16A</td>
    <td>0.980940</td>
    <td>0.149758</td>
    <td>0.802043</td>
    <td>0.047*</td>
  </tr>
  <tr>
    <td>H16B</td>
    <td>1.051172</td>
    <td>0.132186</td>
    <td>0.743621</td>
    <td>0.047*</td>
  </tr>
  <tr>
    <td>H16C</td>
    <td>0.948965</td>
    <td>0.024270</td>
    <td>0.726130</td>
    <td>0.047*</td>
  </tr>
  <tr>
    <td>C18</td>
    <td>0.2741 (6)</td>
    <td>0.2441 (10)</td>
    <td>-0.0937 (4)</td>
    <td>0.0582 (18)</td>
  </tr>
  <tr>
    <td>H18</td>
    <td>0.234602</td>
    <td>0.153747</td>
    <td>-0.115022</td>
    <td>0.070*</td>
  </tr>
  <tr>
    <td>C17</td>
    <td>0.3151 (5)</td>
    <td>0.2832 (8)</td>
    <td>-0.0055 (4)</td>
    <td>0.0493 (16)</td>
  </tr>
  <tr>
    <td>H17</td>
    <td>0.306660</td>
    <td>0.213712</td>
    <td>0.035033</td>
    <td>0.059*</td>
  </tr>
  <tr>
    <td>C26</td>
    <td>0.0565 (4)</td>
    <td>0.7638 (7)</td>
    <td>-0.0421 (4)</td>
    <td>0.0423 (14)</td>
  </tr>
  <tr>
    <td>H26</td>
    <td>-0.016160</td>
    <td>0.810447</td>
    <td>-0.054167</td>
    <td>0.051*</td>
  </tr>
  <tr>
    <td>C21</td>
    <td>0.3804 (4)</td>
    <td>0.5139 (10)</td>
    <td>-0.0254 (4)</td>
    <td>0.0504 (17)</td>
  </tr>
  <tr>
    <td>C28</td>
    <td>0.2479 (5)</td>
    <td>0.8323 (7)</td>
    <td>-0.0237 (4)</td>
    <td>0.0486 (16)</td>
  </tr>
  <tr>
    <td>H28A</td>
    <td>0.293285</td>
    <td>0.915184</td>
    <td>-0.030027</td>
    <td>0.058*</td>
  </tr>
  <tr>
    <td>H28B</td>
    <td>0.247256</td>
    <td>0.751483</td>
    <td>-0.065083</td>
    <td>0.058*</td>
  </tr>
  <tr>
    <td>C32</td>
    <td>-0.0176 (7)</td>
    <td>0.6926 (9)</td>
    <td>-0.2067 (4)</td>
    <td>0.068 (2)</td>
  </tr>
  <tr>
    <td>H32A</td>
    <td>0.032890</td>
    <td>0.756035</td>
    <td>-0.220891</td>
    <td>0.101*</td>
  </tr>
  <tr>
    <td>H32B</td>
    <td>-0.083660</td>
    <td>0.749858</td>
    <td>-0.215141</td>
    <td>0.101*</td>
  </tr>
  <tr>
    <td>H32C</td>
    <td>-0.037751</td>
    <td>0.605256</td>
    <td>-0.246168</td>
    <td>0.101*</td>
  </tr>
  <tr>
    <td>C22</td>
    <td>0.4373 (5)</td>
    <td>0.6511 (10)</td>
    <td>0.0162 (4)</td>
    <td>0.064 (2)</td>
  </tr>
  <tr>
    <td>H22A</td>
    <td>0.416191</td>
    <td>0.732765</td>
    <td>-0.028357</td>
    <td>0.077*</td>
  </tr>
  <tr>
    <td>H22B</td>
    <td>0.517365</td>
    <td>0.635850</td>
    <td>0.038173</td>
    <td>0.077*</td>
  </tr>
  <tr>
    <td>C27</td>
    <td>0.1312 (6)</td>
    <td>0.8883 (7)</td>
    <td>-0.0493 (4)</td>
    <td>0.0552 (18)</td>
  </tr>
  <tr>
    <td>H27A</td>
    <td>0.101814</td>
    <td>0.926492</td>
    <td>-0.111198</td>
    <td>0.066*</td>
  </tr>
</table>
<table><tr><td>H27B</td><td>0.132010</td><td>0.972060</td><td>-0.009604</td><td>0.066*</td></tr><tr><td>C29</td><td>0.3272 (7)</td><td>0.8968 (8)</td><td>0.1403 (5)</td><td>0.068 (2)</td></tr><tr><td>H29A</td><td>0.368891</td><td>0.856492</td><td>0.200143</td><td>0.102*</td></tr><tr><td>H29B</td><td>0.259425</td><td>0.942465</td><td>0.137844</td><td>0.102*</td></tr><tr><td>H29C</td><td>0.371164</td><td>0.972534</td><td>0.126705</td><td>0.102*</td></tr><tr><td>C19</td><td>0.2927 (7)</td><td>0.3391 (10)</td><td>-0.1474 (5)</td><td>0.069 (2)</td></tr><tr><td>H19</td><td>0.270015</td><td>0.312455</td><td>-0.208304</td><td>0.082*</td></tr><tr><td>C20</td><td>0.3427 (6)</td><td>0.4734 (12)</td><td>-0.1196 (4)</td><td>0.070 (2)</td></tr><tr><td>H20</td><td>0.353114</td><td>0.539853</td><td>-0.160608</td><td>0.084*</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>Ni1</td><td>0.01393 (19)</td><td>0.0171 (2)</td><td>0.0136 (2)</td><td>0.0000 (2)</td><td>0.00431 (17)</td><td>0.0017 (2)</td></tr><tr><td>Ni2</td><td>0.0158 (2)</td><td>0.0210 (3)</td><td>0.0153 (2)</td><td>-0.0019 (2)</td><td>0.00406 (17)</td><td>-0.0011 (2)</td></tr><tr><td>Cl2</td><td>0.0180 (4)</td><td>0.0431 (7)</td><td>0.0155 (4)</td><td>0.0016 (4)</td><td>0.0057 (3)</td><td>0.0037 (4)</td></tr><tr><td>Cl3</td><td>0.0178 (4)</td><td>0.0225 (5)</td><td>0.0194 (5)</td><td>0.0017 (4)</td><td>0.0034 (4)</td><td>-0.0031 (4)</td></tr><tr><td>Cl1</td><td>0.0240 (5)</td><td>0.0198 (5)</td><td>0.0244 (5)</td><td>-0.0048 (4)</td><td>0.0031 (4)</td><td>0.0052 (4)</td></tr><tr><td>Cl4</td><td>0.0301 (5)</td><td>0.0180 (5)</td><td>0.0367 (7)</td><td>-0.0042 (4)</td><td>-0.0027 (5)</td><td>0.0021 (5)</td></tr><tr><td>O1</td><td>0.0275 (15)</td><td>0.0233 (17)</td><td>0.0205 (16)</td><td>0.0014 (13)</td><td>0.0077 (13)</td><td>-0.0051 (13)</td></tr><tr><td>N1</td><td>0.0159 (14)</td><td>0.0249 (19)</td><td>0.0133 (16)</td><td>0.0017 (13)</td><td>0.0054 (13)</td><td>0.0017 (14)</td></tr><tr><td>N3</td><td>0.0163 (13)</td><td>0.0206 (17)</td><td>0.0170 (15)</td><td>0.0001 (15)</td><td>0.0056 (12)</td><td>0.0000 (16)</td></tr><tr><td>N2</td><td>0.0122 (13)</td><td>0.0204 (19)</td><td>0.0200 (18)</td><td>0.0019 (13)</td><td>0.0044 (13)</td><td>0.0019 (14)</td></tr><tr><td>O2</td><td>0.0186 (14)</td><td>0.052 (3)</td><td>0.0312 (19)</td><td>-0.0003 (14)</td><td>0.0099 (13)</td><td>0.0128 (17)</td></tr><tr><td>C8</td><td>0.0184 (18)</td><td>0.026 (2)</td><td>0.020 (2)</td><td>0.0079 (16)</td><td>0.0113 (16)</td><td>0.0058 (17)</td></tr><tr><td>C5</td><td>0.0221 (18)</td><td>0.025 (2)</td><td>0.0146 (19)</td><td>0.0034 (17)</td><td>0.0086 (15)</td><td>0.0006 (17)</td></tr><tr><td>N6</td><td>0.0182 (15)</td><td>0.028 (2)</td><td>0.0163 (17)</td><td>0.0011 (13)</td><td>0.0055 (14)</td><td>-0.0007 (14)</td></tr><tr><td>N5</td><td>0.029 (2)</td><td>0.040 (3)</td><td>0.033 (2)</td><td>-0.0178 (19)</td><td>-0.0040 (18)</td><td>0.020 (2)</td></tr><tr><td>C12</td><td>0.0200 (18)</td><td>0.025 (2)</td><td>0.027 (2)</td><td>-0.0009 (17)</td><td>0.0064 (17)</td><td>0.0088 (19)</td></tr><tr><td>C14</td><td>0.0249 (19)</td><td>0.033 (3)</td><td>0.016 (2)</td><td>0.0063 (18)</td><td>0.0045 (16)</td><td>0.0044 (19)</td></tr><tr><td>C3</td><td>0.025 (2)</td><td>0.036 (3)</td><td>0.029 (3)</td><td>0.0125 (19)</td><td>0.0111 (19)</td><td>0.004 (2)</td></tr><tr><td>C9</td><td>0.032 (2)</td><td>0.037 (3)</td><td>0.018 (2)</td><td>0.011 (2)</td><td>0.0145 (18)</td><td>0.006 (2)</td></tr><tr><td>C1</td><td>0.0194 (17)</td><td>0.028 (2)</td><td>0.019 (2)</td><td>0.0006 (16)</td><td>0.0077 (15)</td><td>0.0024 (17)</td></tr><tr><td>C30</td><td>0.035 (2)</td><td>0.041 (3)</td><td>0.033 (3)</td><td>0.006 (2)</td><td>0.015 (2)</td><td>0.000 (2)</td></tr><tr><td>N4</td><td>0.0223 (18)</td><td>0.061 (3)</td><td>0.021 (2)</td><td>0.0157 (19)</td><td>0.0044 (16)</td><td>-0.005 (2)</td></tr><tr><td>C2</td><td>0.0149 (17)</td><td>0.041 (3)</td><td>0.028 (2)</td><td>0.0019 (18)</td><td>0.0097 (17)</td><td>0.007 (2)</td></tr><tr><td>C25</td><td>0.033 (2)</td><td>0.047 (3)</td><td>0.031 (3)</td><td>0.022 (2)</td><td>0.009 (2)</td><td>-0.001 (2)</td></tr><tr><td>C7</td><td>0.0174 (16)</td><td>0.025 (2)</td><td>0.022 (2)</td><td>0.0014 (16)</td><td>0.0105 (15)</td><td>0.0077 (18)</td></tr><tr><td>C4</td><td>0.025 (2)</td><td>0.032 (3)</td><td>0.027 (2)</td><td>0.0106 (18)</td><td>0.0114 (18)</td><td>0.002 (2)</td></tr><tr><td>C24</td><td>0.029 (2)</td><td>0.025 (2)</td><td>0.017 (2)</td><td>0.0080 (18)</td><td>0.0041 (18)</td><td>-0.0052 (18)</td></tr><tr><td>C6</td><td>0.0243 (19)</td><td>0.017 (2)</td><td>0.024 (2)</td><td>0.0046 (16)</td><td>0.0094 (17)</td><td>-0.0026 (17)</td></tr><tr><td>C10</td><td>0.030 (2)</td><td>0.034 (3)</td><td>0.024 (2)</td><td>0.007 (2)</td><td>0.0142 (18)</td><td>0.012 (2)</td></tr><tr><td>C23</td><td>0.048 (3)</td><td>0.015 (2)</td><td>0.032 (3)</td><td>-0.003 (2)</td><td>0.001 (2)</td><td>0.006 (2)</td></tr><tr><td>C15</td><td>0.0204 (19)</td><td>0.036 (3)</td><td>0.028 (2)</td><td>0.0014 (18)</td><td>0.0032 (18)</td><td>0.008 (2)</td></tr><tr><td>C31</td><td>0.0267 (19)</td><td>0.033 (2)</td><td>0.032 (2)</td><td>-0.005 (2)</td><td>0.0058 (18)</td><td>0.001 (3)</td></tr><tr><td>C13</td><td>0.0198 (19)</td><td>0.040 (3)</td><td>0.034 (3)</td><td>-0.001 (2)</td><td>0.0108 (18)</td><td>0.010 (2)</td></tr><tr><td>C11</td><td>0.026 (2)</td><td>0.033 (3)</td><td>0.035 (3)</td><td>0.0008 (19)</td><td>0.015 (2)</td><td>0.018 (2)</td></tr><tr><td>C16</td><td>0.033 (2)</td><td>0.037 (3)</td><td>0.024 (2)</td><td>0.009 (2)</td><td>0.0120 (19)</td><td>0.011 (2)</td></tr></tbody></table>
<table><tr><td>C18</td><td>0.059 (4)</td><td>0.067 (4)</td><td>0.032 (3)</td><td>0.026 (4)</td><td>0.003 (3)</td><td>-0.011 (3)</td></tr><tr><td>C17</td><td>0.040 (3)</td><td>0.057 (4)</td><td>0.032 (3)</td><td>0.025 (3)</td><td>-0.004 (2)</td><td>-0.020 (3)</td></tr><tr><td>C26</td><td>0.043 (3)</td><td>0.047 (4)</td><td>0.028 (3)</td><td>0.027 (3)</td><td>0.005 (2)</td><td>0.002 (2)</td></tr><tr><td>C21</td><td>0.030 (2)</td><td>0.091 (5)</td><td>0.031 (3)</td><td>0.024 (3)</td><td>0.013 (2)</td><td>0.016 (3)</td></tr><tr><td>C28</td><td>0.053 (3)</td><td>0.029 (3)</td><td>0.043 (3)</td><td>-0.005 (3)</td><td>-0.002 (3)</td><td>0.018 (3)</td></tr><tr><td>C32</td><td>0.115 (7)</td><td>0.050 (4)</td><td>0.026 (3)</td><td>0.028 (4)</td><td>0.016 (4)</td><td>0.002 (3)</td></tr><tr><td>C22</td><td>0.033 (3)</td><td>0.113 (7)</td><td>0.049 (4)</td><td>0.010 (3)</td><td>0.020 (3)</td><td>0.057 (4)</td></tr><tr><td>C27</td><td>0.069 (4)</td><td>0.029 (3)</td><td>0.041 (3)</td><td>0.017 (3)</td><td>-0.004 (3)</td><td>0.007 (3)</td></tr><tr><td>C29</td><td>0.091 (5)</td><td>0.027 (3)</td><td>0.051 (4)</td><td>0.000 (3)</td><td>-0.007 (4)</td><td>-0.001 (3)</td></tr><tr><td>C19</td><td>0.093 (6)</td><td>0.071 (5)</td><td>0.055 (4)</td><td>0.014 (4)</td><td>0.044 (4)</td><td>-0.020 (4)</td></tr><tr><td>C20</td><td>0.068 (4)</td><td>0.104 (6)</td><td>0.040 (3)</td><td>0.030 (4)</td><td>0.025 (3)</td><td>0.035 (4)</td></tr></table>

Geometric parameters (Å, °)

<table><tr><td>Ni1—Cl2</td><td>2.4762 (11)</td><td>C2—H2B</td><td>0.9500</td></tr><tr><td>Ni1—Cl3</td><td>2.3964 (10)</td><td>C25—H25A</td><td>0.9900</td></tr><tr><td>Ni1—Cl1</td><td>2.4408 (12)</td><td>C25—H25B</td><td>0.9900</td></tr><tr><td>Ni1—N1</td><td>2.077 (3)</td><td>C25—C24</td><td>1.495 (6)</td></tr><tr><td>Ni1—N3</td><td>2.041 (3)</td><td>C25—C26</td><td>1.536 (8)</td></tr><tr><td>Ni1—N2</td><td>2.126 (4)</td><td>C7—C13</td><td>1.545 (5)</td></tr><tr><td>Ni2—Cl2</td><td>2.4216 (10)</td><td>C4—H4</td><td>0.9500</td></tr><tr><td>Ni2—Cl3</td><td>2.4128 (12)</td><td>C24—C23</td><td>1.516 (7)</td></tr><tr><td>Ni2—Cl4</td><td>2.4077 (14)</td><td>C6—H6A</td><td>0.9900</td></tr><tr><td>Ni2—N6</td><td>2.027 (3)</td><td>C6—H6B</td><td>0.9900</td></tr><tr><td>Ni2—N5</td><td>2.103 (4)</td><td>C10—H10</td><td>1.0000</td></tr><tr><td>Ni2—N4</td><td>2.095 (4)</td><td>C10—C11</td><td>1.540 (8)</td></tr><tr><td>O1—H1</td><td>0.85 (7)</td><td>C23—C28</td><td>1.550 (8)</td></tr><tr><td>O1—N3</td><td>1.403 (5)</td><td>C23—C29</td><td>1.502 (9)</td></tr><tr><td>N1—C5</td><td>1.345 (6)</td><td>C15—H15A</td><td>0.9500</td></tr><tr><td>N1—C1</td><td>1.338 (5)</td><td>C15—H15B</td><td>0.9500</td></tr><tr><td>N3—C8</td><td>1.269 (6)</td><td>C31—H31A</td><td>0.9500</td></tr><tr><td>N2—H2</td><td>0.77 (5)</td><td>C31—H31B</td><td>0.9500</td></tr><tr><td>N2—C7</td><td>1.503 (5)</td><td>C13—H13A</td><td>0.9800</td></tr><tr><td>N2—C6</td><td>1.477 (5)</td><td>C13—H13B</td><td>0.9800</td></tr><tr><td>O2—H2A</td><td>0.76 (8)</td><td>C13—H13C</td><td>0.9800</td></tr><tr><td>O2—N6</td><td>1.385 (5)</td><td>C11—H11A</td><td>0.9900</td></tr><tr><td>C8—C9</td><td>1.509 (6)</td><td>C11—H11B</td><td>0.9900</td></tr><tr><td>C8—C7</td><td>1.513 (7)</td><td>C16—H16A</td><td>0.9800</td></tr><tr><td>C5—C4</td><td>1.385 (6)</td><td>C16—H16B</td><td>0.9800</td></tr><tr><td>C5—C6</td><td>1.508 (6)</td><td>C16—H16C</td><td>0.9800</td></tr><tr><td>N6—C24</td><td>1.269 (6)</td><td>C18—H18</td><td>0.9500</td></tr><tr><td>N5—H5</td><td>0.93 (7)</td><td>C18—C17</td><td>1.370 (8)</td></tr><tr><td>N5—C23</td><td>1.517 (7)</td><td>C18—C19</td><td>1.318 (12)</td></tr><tr><td>N5—C22</td><td>1.524 (9)</td><td>C17—H17</td><td>0.9500</td></tr><tr><td>C12—H12A</td><td>0.9900</td><td>C26—H26</td><td>1.0000</td></tr><tr><td>C12—H12B</td><td>0.9900</td><td>C26—C27</td><td>1.532 (10)</td></tr><tr><td>C12—C7</td><td>1.555 (6)</td><td>C21—C22</td><td>1.457 (12)</td></tr><tr><td>C12—C11</td><td>1.528 (7)</td><td>C21—C20</td><td>1.465 (10)</td></tr></table>
<table>
  <tr>
    <td>C14—C10</td>
    <td>1.523 (6)</td>
    <td>C28—H28A</td>
    <td>0.9900</td>
  </tr>
  <tr>
    <td>C14—C15</td>
    <td>1.326 (7)</td>
    <td>C28—H28B</td>
    <td>0.9900</td>
  </tr>
  <tr>
    <td>C14—C16</td>
    <td>1.506 (7)</td>
    <td>C28—C27</td>
    <td>1.525 (9)</td>
  </tr>
  <tr>
    <td>C3—H3</td>
    <td>0.9500</td>
    <td>C32—H32A</td>
    <td>0.9800</td>
  </tr>
  <tr>
    <td>C3—C2</td>
    <td>1.373 (8)</td>
    <td>C32—H32B</td>
    <td>0.9800</td>
  </tr>
  <tr>
    <td>C3—C4</td>
    <td>1.384 (7)</td>
    <td>C32—H32C</td>
    <td>0.9800</td>
  </tr>
  <tr>
    <td>C9—H9A</td>
    <td>0.9900</td>
    <td>C22—H22A</td>
    <td>0.9900</td>
  </tr>
  <tr>
    <td>C9—H9B</td>
    <td>0.9900</td>
    <td>C22—H22B</td>
    <td>0.9900</td>
  </tr>
  <tr>
    <td>C9—C10</td>
    <td>1.545 (7)</td>
    <td>C27—H27A</td>
    <td>0.9900</td>
  </tr>
  <tr>
    <td>C1—H1A</td>
    <td>0.9500</td>
    <td>C27—H27B</td>
    <td>0.9900</td>
  </tr>
  <tr>
    <td>C1—C2</td>
    <td>1.396 (6)</td>
    <td>C29—H29A</td>
    <td>0.9800</td>
  </tr>
  <tr>
    <td>C30—C31</td>
    <td>1.318 (8)</td>
    <td>C29—H29B</td>
    <td>0.9800</td>
  </tr>
  <tr>
    <td>C30—C26</td>
    <td>1.521 (8)</td>
    <td>C29—H29C</td>
    <td>0.9800</td>
  </tr>
  <tr>
    <td>C30—C32</td>
    <td>1.503 (8)</td>
    <td>C19—H19</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>N4—C17</td>
    <td>1.359 (8)</td>
    <td>C19—C20</td>
    <td>1.360 (13)</td>
  </tr>
  <tr>
    <td>N4—C21</td>
    <td>1.314 (8)</td>
    <td>C20—H20</td>
    <td>0.9500</td>
  </tr>
</table>

<table>
  <tr>
    <td>Cl3—Ni1—Cl2</td>
    <td>84.13 (4)</td>
    <td>C8—C7—C13</td>
    <td>108.0 (4)</td>
  </tr>
  <tr>
    <td>Cl3—Ni1—Cl1</td>
    <td>91.99 (4)</td>
    <td>C13—C7—C12</td>
    <td>110.9 (4)</td>
  </tr>
  <tr>
    <td>Cl1—Ni1—Cl2</td>
    <td>100.61 (4)</td>
    <td>C5—C4—H4</td>
    <td>120.7</td>
  </tr>
  <tr>
    <td>N1—Ni1—Cl2</td>
    <td>88.69 (10)</td>
    <td>C3—C4—C5</td>
    <td>118.5 (5)</td>
  </tr>
  <tr>
    <td>N1—Ni1—Cl3</td>
    <td>171.31 (10)</td>
    <td>C3—C4—H4</td>
    <td>120.7</td>
  </tr>
  <tr>
    <td>N1—Ni1—Cl1</td>
    <td>94.14 (11)</td>
    <td>N6—C24—C25</td>
    <td>124.3 (5)</td>
  </tr>
  <tr>
    <td>N1—Ni1—N2</td>
    <td>79.91 (13)</td>
    <td>N6—C24—C23</td>
    <td>116.7 (4)</td>
  </tr>
  <tr>
    <td>N3—Ni1—Cl2</td>
    <td>170.10 (12)</td>
    <td>C25—C24—C23</td>
    <td>118.8 (4)</td>
  </tr>
  <tr>
    <td>N3—Ni1—Cl3</td>
    <td>94.30 (9)</td>
    <td>N2—C6—C5</td>
    <td>110.5 (4)</td>
  </tr>
  <tr>
    <td>N3—Ni1—Cl1</td>
    <td>89.21 (12)</td>
    <td>N2—C6—H6A</td>
    <td>109.6</td>
  </tr>
  <tr>
    <td>N3—Ni1—N1</td>
    <td>91.94 (13)</td>
    <td>N2—C6—H6B</td>
    <td>109.6</td>
  </tr>
  <tr>
    <td>N3—Ni1—N2</td>
    <td>77.38 (15)</td>
    <td>C5—C6—H6A</td>
    <td>109.6</td>
  </tr>
  <tr>
    <td>N2—Ni1—Cl2</td>
    <td>93.02 (10)</td>
    <td>C5—C6—H6B</td>
    <td>109.6</td>
  </tr>
  <tr>
    <td>N2—Ni1—Cl3</td>
    <td>95.56 (9)</td>
    <td>H6A—C6—H6B</td>
    <td>108.1</td>
  </tr>
  <tr>
    <td>N2—Ni1—Cl1</td>
    <td>165.04 (11)</td>
    <td>C14—C10—C9</td>
    <td>114.7 (4)</td>
  </tr>
  <tr>
    <td>Cl3—Ni2—Cl2</td>
    <td>84.97 (4)</td>
    <td>C14—C10—H10</td>
    <td>106.7</td>
  </tr>
  <tr>
    <td>Cl4—Ni2—Cl2</td>
    <td>99.38 (4)</td>
    <td>C14—C10—C11</td>
    <td>111.4 (4)</td>
  </tr>
  <tr>
    <td>Cl4—Ni2—Cl3</td>
    <td>93.14 (5)</td>
    <td>C9—C10—H10</td>
    <td>106.7</td>
  </tr>
  <tr>
    <td>N6—Ni2—Cl2</td>
    <td>171.72 (12)</td>
    <td>C11—C10—C9</td>
    <td>110.3 (4)</td>
  </tr>
  <tr>
    <td>N6—Ni2—Cl3</td>
    <td>92.13 (11)</td>
    <td>C11—C10—H10</td>
    <td>106.7</td>
  </tr>
  <tr>
    <td>N6—Ni2—Cl4</td>
    <td>88.51 (11)</td>
    <td>N5—C23—C28</td>
    <td>112.0 (5)</td>
  </tr>
  <tr>
    <td>N6—Ni2—N5</td>
    <td>79.29 (16)</td>
    <td>C24—C23—N5</td>
    <td>109.5 (4)</td>
  </tr>
  <tr>
    <td>N6—Ni2—N4</td>
    <td>88.11 (15)</td>
    <td>C24—C23—C28</td>
    <td>108.9 (4)</td>
  </tr>
  <tr>
    <td>N5—Ni2—Cl2</td>
    <td>93.15 (13)</td>
    <td>C29—C23—N5</td>
    <td>104.7 (5)</td>
  </tr>
  <tr>
    <td>N5—Ni2—Cl3</td>
    <td>94.06 (15)</td>
    <td>C29—C23—C24</td>
    <td>109.9 (5)</td>
  </tr>
  <tr>
    <td>N5—Ni2—Cl4</td>
    <td>166.04 (12)</td>
    <td>C29—C23—C28</td>
    <td>111.8 (5)</td>
  </tr>
  <tr>
    <td>N4—Ni2—Cl2</td>
    <td>93.92 (11)</td>
    <td>C14—C15—H15A</td>
    <td>120.0</td>
  </tr>
  <tr>
    <td>N4—Ni2—Cl3</td>
    <td>173.62 (15)</td>
    <td>C14—C15—H15B</td>
    <td>120.0</td>
  </tr>
  <tr>
    <td>N4—Ni2—Cl4</td>
    <td>93.24 (16)</td>
    <td>H15A—C15—H15B</td>
    <td>120.0</td>
  </tr>
  <tr>
    <td>N4—Ni2—N5</td>
    <td>79.7 (2)</td>
    <td>C30—C31—H31A</td>
    <td>120.0</td>
  </tr>
  <tr>
    <td>Ni2—Cl2—Ni1</td>
    <td>91.88 (4)</td>
    <td>C30—C31—H31B</td>
    <td>120.0</td>
  </tr>
</table>
<table>
  <tr>
    <td>Ni1—Cl3—Ni2</td>
    <td>94.09 (4)</td>
  </tr>
  <tr>
    <td>N3—O1—H1</td>
    <td>111 (4)</td>
  </tr>
  <tr>
    <td>C5—N1—Ni1</td>
    <td>113.6 (3)</td>
  </tr>
  <tr>
    <td>C1—N1—Ni1</td>
    <td>127.6 (3)</td>
  </tr>
  <tr>
    <td>C1—N1—C5</td>
    <td>118.8 (4)</td>
  </tr>
  <tr>
    <td>O1—N3—Ni1</td>
    <td>121.4 (3)</td>
  </tr>
  <tr>
    <td>C8—N3—Ni1</td>
    <td>122.2 (3)</td>
  </tr>
  <tr>
    <td>C8—N3—O1</td>
    <td>115.9 (3)</td>
  </tr>
  <tr>
    <td>Ni1—N2—H2</td>
    <td>93 (4)</td>
  </tr>
  <tr>
    <td>C7—N2—Ni1</td>
    <td>113.6 (3)</td>
  </tr>
  <tr>
    <td>C7—N2—H2</td>
    <td>116 (4)</td>
  </tr>
  <tr>
    <td>C6—N2—Ni1</td>
    <td>104.0 (2)</td>
  </tr>
  <tr>
    <td>C6—N2—H2</td>
    <td>109 (4)</td>
  </tr>
  <tr>
    <td>C6—N2—C7</td>
    <td>118.1 (3)</td>
  </tr>
  <tr>
    <td>N6—O2—H2A</td>
    <td>105 (5)</td>
  </tr>
  <tr>
    <td>N3—C8—C9</td>
    <td>124.7 (4)</td>
  </tr>
  <tr>
    <td>N3—C8—C7</td>
    <td>116.1 (4)</td>
  </tr>
  <tr>
    <td>C9—C8—C7</td>
    <td>119.2 (4)</td>
  </tr>
  <tr>
    <td>N1—C5—C4</td>
    <td>122.3 (4)</td>
  </tr>
  <tr>
    <td>N1—C5—C6</td>
    <td>115.1 (4)</td>
  </tr>
  <tr>
    <td>C4—C5—C6</td>
    <td>122.6 (4)</td>
  </tr>
  <tr>
    <td>O2—N6—Ni2</td>
    <td>122.4 (3)</td>
  </tr>
  <tr>
    <td>C24—N6—Ni2</td>
    <td>120.3 (3)</td>
  </tr>
  <tr>
    <td>C24—N6—O2</td>
    <td>116.7 (4)</td>
  </tr>
  <tr>
    <td>Ni2—N5—H5</td>
    <td>94 (4)</td>
  </tr>
  <tr>
    <td>C23—N5—Ni2</td>
    <td>112.0 (3)</td>
  </tr>
  <tr>
    <td>C23—N5—H5</td>
    <td>115 (4)</td>
  </tr>
  <tr>
    <td>C23—N5—C22</td>
    <td>118.6 (4)</td>
  </tr>
  <tr>
    <td>C22—N5—Ni2</td>
    <td>102.9 (4)</td>
  </tr>
  <tr>
    <td>C22—N5—H5</td>
    <td>110 (4)</td>
  </tr>
  <tr>
    <td>H12A—C12—H12B</td>
    <td>107.8</td>
  </tr>
  <tr>
    <td>C7—C12—H12A</td>
    <td>109.0</td>
  </tr>
  <tr>
    <td>C7—C12—H12B</td>
    <td>109.0</td>
  </tr>
  <tr>
    <td>C11—C12—H12A</td>
    <td>109.0</td>
  </tr>
  <tr>
    <td>C11—C12—H12B</td>
    <td>109.0</td>
  </tr>
  <tr>
    <td>C11—C12—C7</td>
    <td>113.0 (4)</td>
  </tr>
  <tr>
    <td>C15—C14—C10</td>
    <td>124.9 (4)</td>
  </tr>
  <tr>
    <td>C15—C14—C16</td>
    <td>120.2 (4)</td>
  </tr>
  <tr>
    <td>C16—C14—C10</td>
    <td>114.9 (4)</td>
  </tr>
  <tr>
    <td>C2—C3—H3</td>
    <td>120.1</td>
  </tr>
  <tr>
    <td>C2—C3—C4</td>
    <td>119.7 (4)</td>
  </tr>
  <tr>
    <td>C4—C3—H3</td>
    <td>120.1</td>
  </tr>
  <tr>
    <td>C8—C9—H9A</td>
    <td>109.2</td>
  </tr>
  <tr>
    <td>C8—C9—H9B</td>
    <td>109.2</td>
  </tr>
  <tr>
    <td>C8—C9—C10</td>
    <td>112.2 (4)</td>
  </tr>
  <tr>
    <td>H9A—C9—H9B</td>
    <td>107.9</td>
  </tr>
  <tr>
    <td>C10—C9—H9A</td>
    <td>109.2</td>
  </tr>
  <tr>
    <td>C10—C9—H9B</td>
    <td>109.2</td>
  </tr>
</table>

<table>
  <tr>
    <td>H31A—C31—H31B</td>
    <td>120.0</td>
  </tr>
  <tr>
    <td>C7—C13—H13A</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>C7—C13—H13B</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>C7—C13—H13C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H13A—C13—H13B</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H13A—C13—H13C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H13B—C13—H13C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>C12—C11—C10</td>
    <td>112.0 (4)</td>
  </tr>
  <tr>
    <td>C12—C11—H11A</td>
    <td>109.2</td>
  </tr>
  <tr>
    <td>C12—C11—H11B</td>
    <td>109.2</td>
  </tr>
  <tr>
    <td>C10—C11—H11A</td>
    <td>109.2</td>
  </tr>
  <tr>
    <td>C10—C11—H11B</td>
    <td>109.2</td>
  </tr>
  <tr>
    <td>H11A—C11—H11B</td>
    <td>107.9</td>
  </tr>
  <tr>
    <td>C14—C16—H16A</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>C14—C16—H16B</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>C14—C16—H16C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H16A—C16—H16B</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H16A—C16—H16C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H16B—C16—H16C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>C17—C18—H18</td>
    <td>121.9</td>
  </tr>
  <tr>
    <td>C19—C18—H18</td>
    <td>121.9</td>
  </tr>
  <tr>
    <td>C19—C18—C17</td>
    <td>116.1 (8)</td>
  </tr>
  <tr>
    <td>N4—C17—C18</td>
    <td>124.7 (7)</td>
  </tr>
  <tr>
    <td>N4—C17—H17</td>
    <td>117.7</td>
  </tr>
  <tr>
    <td>C18—C17—H17</td>
    <td>117.7</td>
  </tr>
  <tr>
    <td>C30—C26—C25</td>
    <td>114.3 (5)</td>
  </tr>
  <tr>
    <td>C30—C26—H26</td>
    <td>107.1</td>
  </tr>
  <tr>
    <td>C30—C26—C27</td>
    <td>112.5 (5)</td>
  </tr>
  <tr>
    <td>C25—C26—H26</td>
    <td>107.1</td>
  </tr>
  <tr>
    <td>C27—C26—C25</td>
    <td>108.5 (5)</td>
  </tr>
  <tr>
    <td>C27—C26—H26</td>
    <td>107.1</td>
  </tr>
  <tr>
    <td>N4—C21—C22</td>
    <td>116.4 (5)</td>
  </tr>
  <tr>
    <td>N4—C21—C20</td>
    <td>117.2 (8)</td>
  </tr>
  <tr>
    <td>C22—C21—C20</td>
    <td>126.3 (7)</td>
  </tr>
  <tr>
    <td>C23—C28—H28A</td>
    <td>109.2</td>
  </tr>
  <tr>
    <td>C23—C28—H28B</td>
    <td>109.2</td>
  </tr>
  <tr>
    <td>H28A—C28—H28B</td>
    <td>107.9</td>
  </tr>
  <tr>
    <td>C27—C28—C23</td>
    <td>112.2 (6)</td>
  </tr>
  <tr>
    <td>C27—C28—H28A</td>
    <td>109.2</td>
  </tr>
  <tr>
    <td>C27—C28—H28B</td>
    <td>109.2</td>
  </tr>
  <tr>
    <td>C30—C32—H32A</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>C30—C32—H32B</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>C30—C32—H32C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H32A—C32—H32B</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H32A—C32—H32C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H32B—C32—H32C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>N5—C22—H22A</td>
    <td>109.7</td>
  </tr>
  <tr>
    <td>N5—C22—H22B</td>
    <td>109.7</td>
  </tr>
</table>
<table><tr><td>N1—C1—H1A</td><td>119.0</td></tr><tr><td>N1—C1—C2</td><td>122.1 (4)</td></tr><tr><td>C2—C1—H1A</td><td>119.0</td></tr><tr><td>C31—C30—C26</td><td>124.8 (5)</td></tr><tr><td>C31—C30—C32</td><td>120.1 (5)</td></tr><tr><td>C32—C30—C26</td><td>115.1 (5)</td></tr><tr><td>C17—N4—Ni2</td><td>126.7 (4)</td></tr><tr><td>C21—N4—Ni2</td><td>113.2 (4)</td></tr><tr><td>C21—N4—C17</td><td>119.9 (5)</td></tr><tr><td>C3—C2—C1</td><td>118.6 (4)</td></tr><tr><td>C3—C2—H2B</td><td>120.7</td></tr><tr><td>C1—C2—H2B</td><td>120.7</td></tr><tr><td>H25A—C25—H25B</td><td>107.9</td></tr><tr><td>C24—C25—H25A</td><td>109.2</td></tr><tr><td>C24—C25—H25B</td><td>109.2</td></tr><tr><td>C24—C25—C26</td><td>112.1 (4)</td></tr><tr><td>C26—C25—H25A</td><td>109.2</td></tr><tr><td>C26—C25—H25B</td><td>109.2</td></tr><tr><td>N2—C7—C8</td><td>109.8 (3)</td></tr><tr><td>N2—C7—C12</td><td>112.5 (3)</td></tr><tr><td>N2—C7—C13</td><td>107.1 (3)</td></tr><tr><td>C8—C7—C12</td><td>108.5 (3)</td></tr></table>

<table><tr><td>Ni1—N1—C5—C4</td><td>-178.5 (3)</td></tr><tr><td>Ni1—N1—C5—C6</td><td>2.4 (4)</td></tr><tr><td>Ni1—N1—C1—C2</td><td>177.8 (3)</td></tr><tr><td>Ni1—N3—C8—C9</td><td>171.5 (3)</td></tr><tr><td>Ni1—N3—C8—C7</td><td>-10.6 (5)</td></tr><tr><td>Ni1—N2—C7—C8</td><td>-7.7 (4)</td></tr><tr><td>Ni1—N2—C7—C12</td><td>-128.6 (3)</td></tr><tr><td>Ni1—N2—C7—C13</td><td>109.3 (4)</td></tr><tr><td>Ni1—N2—C6—C5</td><td>43.4 (4)</td></tr><tr><td>Ni2—N6—C24—C25</td><td>173.2 (4)</td></tr><tr><td>Ni2—N6—C24—C23</td><td>-12.5 (6)</td></tr><tr><td>Ni2—N5—C23—C24</td><td>-13.2 (5)</td></tr><tr><td>Ni2—N5—C23—C28</td><td>-134.2 (4)</td></tr><tr><td>Ni2—N5—C23—C29</td><td>104.5 (5)</td></tr><tr><td>Ni2—N5—C22—C21</td><td>44.6 (5)</td></tr><tr><td>Ni2—N4—C17—C18</td><td>174.2 (4)</td></tr><tr><td>Ni2—N4—C21—C22</td><td>5.4 (6)</td></tr><tr><td>Ni2—N4—C21—C20</td><td>-178.0 (4)</td></tr><tr><td>O1—N3—C8—C9</td><td>-0.7 (6)</td></tr><tr><td>O1—N3—C8—C7</td><td>177.3 (3)</td></tr><tr><td>N1—C5—C4—C3</td><td>1.0 (7)</td></tr><tr><td>N1—C5—C6—N2</td><td>-32.3 (5)</td></tr><tr><td>N1—C1—C2—C3</td><td>-0.2 (7)</td></tr><tr><td>N3—C8—C9—C10</td><td>-134.2 (4)</td></tr><tr><td>N3—C8—C7—N2</td><td>11.5 (5)</td></tr></table>

<table><tr><td>C21—C22—N5</td><td>110.0 (4)</td></tr><tr><td>C21—C22—H22A</td><td>109.7</td></tr><tr><td>C21—C22—H22B</td><td>109.7</td></tr><tr><td>H22A—C22—H22B</td><td>108.2</td></tr><tr><td>C26—C27—H27A</td><td>109.3</td></tr><tr><td>C26—C27—H27B</td><td>109.3</td></tr><tr><td>C28—C27—C26</td><td>111.5 (5)</td></tr><tr><td>C28—C27—H27A</td><td>109.3</td></tr><tr><td>C28—C27—H27B</td><td>109.3</td></tr><tr><td>H27A—C27—H27B</td><td>108.0</td></tr><tr><td>C23—C29—H29A</td><td>109.5</td></tr><tr><td>C23—C29—H29B</td><td>109.5</td></tr><tr><td>C23—C29—H29C</td><td>109.5</td></tr><tr><td>H29A—C29—H29B</td><td>109.5</td></tr><tr><td>H29A—C29—H29C</td><td>109.5</td></tr><tr><td>H29B—C29—H29C</td><td>109.5</td></tr><tr><td>C18—C19—H19</td><td>118.5</td></tr><tr><td>C18—C19—C20</td><td>123.0 (7)</td></tr><tr><td>C20—C19—H19</td><td>118.5</td></tr><tr><td>C21—C20—H20</td><td>120.5</td></tr><tr><td>C19—C20—C21</td><td>119.0 (7)</td></tr><tr><td>C19—C20—H20</td><td>120.5</td></tr></table>

<table><tr><td>N4—C21—C20—C19</td><td>2.4 (9)</td></tr><tr><td>C2—C3—C4—C5</td><td>-0.9 (7)</td></tr><tr><td>C25—C24—C23—N5</td><td>-168.7 (4)</td></tr><tr><td>C25—C24—C23—C28</td><td>-45.9 (6)</td></tr><tr><td>C25—C24—C23—C29</td><td>76.9 (6)</td></tr><tr><td>C25—C26—C27—C28</td><td>59.6 (6)</td></tr><tr><td>C7—N2—C6—C5</td><td>-83.5 (4)</td></tr><tr><td>C7—C8—C9—C10</td><td>47.9 (5)</td></tr><tr><td>C7—C12—C11—C10</td><td>-57.9 (5)</td></tr><tr><td>C4—C5—C6—N2</td><td>148.6 (4)</td></tr><tr><td>C4—C3—C2—C1</td><td>0.6 (7)</td></tr><tr><td>C24—C25—C26—C30</td><td>73.6 (6)</td></tr><tr><td>C24—C25—C26—C27</td><td>-52.8 (6)</td></tr><tr><td>C24—C23—C28—C27</td><td>49.5 (6)</td></tr><tr><td>C6—N2—C7—C8</td><td>114.5 (4)</td></tr><tr><td>C6—N2—C7—C12</td><td>-6.5 (5)</td></tr><tr><td>C6—N2—C7—C13</td><td>-128.6 (4)</td></tr><tr><td>C6—C5—C4—C3</td><td>180.0 (4)</td></tr><tr><td>C23—N5—C22—C21</td><td>-79.6 (6)</td></tr><tr><td>C23—C28—C27—C26</td><td>-59.7 (7)</td></tr><tr><td>C15—C14—C10—C9</td><td>-24.5 (7)</td></tr><tr><td>C15—C14—C10—C11</td><td>101.6 (6)</td></tr><tr><td>C31—C30—C26—C25</td><td>-6.7 (8)</td></tr><tr><td>C31—C30—C26—C27</td><td>117.5 (6)</td></tr><tr><td>C11—C12—C7—N2</td><td>172.3 (3)</td></tr></table>
<table><caption>Hydrogen-bond geometry (Å, °)</caption><tr><td>N3—C8—C7—C12</td><td>134.8 (4)</td><td>C11—C12—C7—C8</td><td>50.6 (4)</td></tr><tr><td>N3—C8—C7—C13</td><td>-104.9 (4)</td><td>C11—C12—C7—C13</td><td>-67.8 (5)</td></tr><tr><td>O2—N6—C24—C25</td><td>1.3 (6)</td><td>C16—C14—C10—C9</td><td>158.2 (4)</td></tr><tr><td>O2—N6—C24—C23</td><td>175.6 (4)</td><td>C16—C14—C10—C11</td><td>-75.7 (5)</td></tr><tr><td>C8—C9—C10—C14</td><td>77.6 (5)</td><td>C18—C19—C20—C21</td><td>1.5 (12)</td></tr><tr><td>C8—C9—C10—C11</td><td>-49.1 (5)</td><td>C17—N4—C21—C22</td><td>-179.7 (5)</td></tr><tr><td>C5—N1—C1—C2</td><td>0.3 (6)</td><td>C17—N4—C21—C20</td><td>-3.0 (7)</td></tr><tr><td>N6—C24—C23—N5</td><td>16.7 (6)</td><td>C17—C18—C19—C20</td><td>-4.4 (11)</td></tr><tr><td>N6—C24—C23—C28</td><td>139.5 (5)</td><td>C26—C25—C24—N6</td><td>-136.7 (5)</td></tr><tr><td>N6—C24—C23—C29</td><td>-97.7 (5)</td><td>C26—C25—C24—C23</td><td>49.2 (7)</td></tr><tr><td>N5—C23—C28—C27</td><td>170.8 (5)</td><td>C21—N4—C17—C18</td><td>0.0 (8)</td></tr><tr><td>C14—C10—C11—C12</td><td>-72.9 (5)</td><td>C32—C30—C26—C25</td><td>174.8 (6)</td></tr><tr><td>C9—C8—C7—N2</td><td>-170.4 (3)</td><td>C32—C30—C26—C27</td><td>-60.9 (7)</td></tr><tr><td>C9—C8—C7—C12</td><td>-47.1 (5)</td><td>C22—N5—C23—C24</td><td>106.3 (6)</td></tr><tr><td>C9—C8—C7—C13</td><td>73.2 (5)</td><td>C22—N5—C23—C28</td><td>-14.6 (6)</td></tr><tr><td>C9—C10—C11—C12</td><td>55.6 (5)</td><td>C22—N5—C23—C29</td><td>-135.9 (6)</td></tr><tr><td>C1—N1—C5—C4</td><td>-0.6 (6)</td><td>C22—C21—C20—C19</td><td>178.6 (6)</td></tr><tr><td>C1—N1—C5—C6</td><td>-179.7 (4)</td><td>C29—C23—C28—C27</td><td>-72.1 (7)</td></tr><tr><td>C30—C26—C27—C28</td><td>-67.9 (6)</td><td>C19—C18—C17—N4</td><td>3.8 (9)</td></tr><tr><td>N4—C21—C22—N5</td><td>-35.0 (7)</td><td>C20—C21—C22—N5</td><td>148.7 (6)</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>O1—H1···Cl1</td><td>0.85 (7)</td><td>2.32 (6)</td><td>3.009 (4)</td><td>139 (6)</td></tr><tr><td>N2—H2···Cl4</td><td>0.77 (5)</td><td>2.46 (5)</td><td>3.209 (4)</td><td>166 (5)</td></tr><tr><td>O2—H2A···Cl4</td><td>0.76 (8)</td><td>2.31 (7)</td><td>2.978 (4)</td><td>147 (7)</td></tr><tr><td>C3—H3···O1<sup>i</sup></td><td>0.95</td><td>2.58</td><td>3.432 (5)</td><td>149</td></tr><tr><td>C1—H1A···Cl1</td><td>0.95</td><td>2.75</td><td>3.369 (5)</td><td>124</td></tr><tr><td>C6—H6A···Cl2</td><td>0.99</td><td>2.76</td><td>3.309 (5)</td><td>115</td></tr><tr><td>C11—H11B···Cl3<sup>ii</sup></td><td>0.99</td><td>2.64</td><td>3.573 (5)</td><td>156</td></tr><tr><td>C17—H17···Cl4</td><td>0.95</td><td>2.69</td><td>3.327 (6)</td><td>125</td></tr><tr><td>C26—H26···O2<sup>iii</sup></td><td>1.00</td><td>2.56</td><td>3.489 (6)</td><td>154</td></tr><tr><td>C22—H22B···Cl2</td><td>0.99</td><td>2.81</td><td>3.352 (6)</td><td>115</td></tr><tr><td>C19—H19···Cl1<sup>iv</sup></td><td>0.95</td><td>2.64</td><td>3.570 (7)</td><td>167</td></tr></tbody></table>

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