Crystal structure of
4-[10,15,20-tris(4-methoxy-phenyl)porphyrin-5-yl]benzyl
2-diazoacetato-zinc(II)

Daniel Carrie, Thierry Roisnel, Gerard Simonneaux

► To cite this version:

Daniel Carrie, Thierry Roisnel, Gerard Simonneaux. Crystal structure of 4-[10,15,20-tris(4-methoxy-phenyl)porphyrin-5-yl]benzyl 2-diazoacetato-zinc(II). Acta crystallographica Section E: Crystallographic communications [2015-..], 2020, 76 (2), pp.273-275. 10.1107/S2056989020001085 . hal-02498317

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Acta Cryst.

E

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN 2056-9890

Received 5 December 2019

Accepted 27 January 2020

Edited by W. T. A. Harrison, University of
Aberdeen, Scotland

**Keywords:** crystal structure; diazo ester; porphyrin; zinc.

CCDC reference: 1968288

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

# Crystal structure of {4-[10,15,20-tris(4-methoxy-phenyl)porphyrin-5-yl]benzyl 2-diazoacetato}-zinc(II)

Daniel Carrie, Thierry Roisnel and Gerard Simonneaux*

Univ Rennes, CNRS, ISCR-UMR6226, F-35000 Rennes, France. *Correspondence e-mail: gerard.simonneaux@univ-rennes1.fr

In the title compound, [Zn(C50H36N6O5)], the ZnII cation is chelated by four pyrrole N atoms of the porphyrinate anion and coordinated by a symmetry-generated keto O atom of the diazoester group in a distorted square-pyramidal geometry. The mean Zn—N(pyrrole) bond length is 2.058 Å and the Zn—O(diazoester) bond length is 2.179 (4) Å. The zinc cation is displaced by 0.2202 (13) Å from the N4C20 mean plane of the porphyrinate anion toward the O atom; the involvement of this atom leads to a [100] polymeric chain in the crystal.

## 1. Chemical context

Among various functional groups, diazo derivatives are particularly attractive because of their high reactivities (Ye & McKervey, 1994). Since porphyrin macrocycles are important fluorescent probes, their functionalization by a diazo group may have many chemical and biological applications (Mix *et al.*, 2016). However, the present study of the title compound seems to be the only reported X-ray structure of a porphyrin bearing a diazo ester group at the periphery of a porphyrin ring. In contrast, many structures of five-coordinate zinc porphyrins of the type [Zn(Porph)(L)] (Porph = is a porphinato ligand and L is a neutral ligand) are known in the literature (Nasri *et al.*, 2016). During the course of our previous studies on diazo compounds (Ferrand *et al.*, 2005; Galardon *et al.*, 2000), we reported the use of metalloporphyrins for catalytic cyclopropanation and the insertion of diazoketone compounds in N—H bonds. (Nicolas *et al.*, 2008, Nicolas *et al.*, 2009).

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

In this work, we describe the crystal structure of the zinc porphyrin title complex, (I), to obtain more insight into the

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

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

OPEN ACCESS
<figure><img src="image_6.png" /><figcaption>**Figure 1**
The molecular structure of (I) showing 50% displacement ellipsoids.</figcaption></figure>

structural relationship of zinc and a diazoester group (Carrie *et al.*, 2016; Fleischer & Shachter, 1991)

**2. Structural commentary**

The asymmetric unit of (I) is shown in Fig. 1. In the crystal, the structure is a one-dimensional polymer, wherein the Zn²⁺ ion bonds to four pyrrole nitrogen atoms and to the diazo ester oxygen atom of an adjacent molecule [O60¹: symmetry code: (i) x − 1, y, z], thereby defining the propagation of the chain, Figs. 2 and 3. The bond lengths from the zinc ion to the pyrrole nitrogen atoms span the range 2.046 (4)–2.073 (4) Å, which is comparable with those reported in the literature (Nasri *et al.*, 2016). The Zn—O(diazoester) bond length is 2.179 (4) Å, which is slightly shorter than that of ZnTCPP(acetone) (TCPP = meso-tetra(4-carboxyphenyl)porphyrin) [2.222 (2) Å; Chen *et al.*, 2014]. The bond lengths of the diazo group have been previously estimated from X-ray data and *ab initio* calculations for a series of diazocompounds (average parameters: N—N 1.1189 and N—C = 1.3263 Å). Remarkably little

<figure><img src="image_7.png" /><figcaption>**Figure 3**
The packing of (I) showing side-by-side polymeric chains propagating in the [100] direction.</figcaption></figure>

variance in these bond lengths occurs, even with varied functionality around the diazo moiety (Goodman *et al.*, 1994). For the title compound, the N—N and C—N bond lengths are 1.112 (10) and 1.285 (10) Å, respectively, which are close to those observed for an aromatic diazoketone [N—N = 1.117 (8); C—N = 1.316 (9) Å; Yanez *et al.*, 2003].

**3. Supramolecular features**

Fig. 2 shows the polymeric nature of (I) consisting of infinite [100] chains of Zn porphyrin units with the diazoester of one unit coordinated to the zinc atom of another: the molecules are linked together in such a way as to make two different columns of porphyrin planes (Fig. 3). There are no other significant intermolecular contacts present.

**4. Synthesis and crystallization**

5-[4-(Hydroxymethyl)phenyl]-10,15,20-(4-(trimethoxy)phenyl)porphyrin and the zinc starting complex were synthesized using previously reported methods (Carrie *et al.*, 2016).

To a distilled CH₂Cl₂ solution (5 ml) of zinc 5-[4-(hydroxymethyl)phenyl]-10,15,20-triphenylporphyrin (100 mg, 0.12 mmol), 3 eq. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU; 0.36 mmol) were first added under argon at 273 K and then 1.5 eq. of bromo acetyl bromide (0.2 mmol). The reaction mixture was stirred for 10 min at room temperature. After cooling the solution again to 273 K, a THF solution of ditosylhydrazine (2 eq.) and DBU (5 eq.) was added, and the mixture was stirred for 30 min at room temperature. The solution was then evaporated, dissolved in CH₂Cl₂ and purified through a silica gel column (CH₂Cl₂). Yield = 70%. Red prisms of (I) were obtained by diffusion of pentane into a dichloromethane solution. UV/VIS (CH₂Cl₂): lmax, nm: 421, 548, 592.

**5. Refinement**

Crystal data, data collection and structure refinement details are summarized in Table 1. The contribution of the disordered solvents to the calculated structure factors was estimated

<figure><img src="image_8.png" /><figcaption>**Figure 2**
Fragment of the polymeric structure of (I): atoms Zn1_1 and O60_1 are generated by the symmetry operations x + 1, y, z and x − 1, y, z, respectively.</figcaption></figure>
<table><caption>**Table 1**
Experimental details.</caption><thead><tr><th></th><th></th></tr></thead><tbody><tr><td>Crystal data</td><td></td></tr><tr><td>Chemical formula</td><td>[Zn(C<sub>50</sub>H<sub>36</sub>N<sub>6</sub>O<sub>5</sub>)]</td></tr><tr><td>M<sub>r</sub></td><td>866.22</td></tr><tr><td>Crystal system, space group</td><td>Monoclinic, P2<sub>1</sub></td></tr><tr><td>Temperature (K)</td><td>150</td></tr><tr><td>a, b, c (Å)</td><td>10.8054 (8), 19.3938 (14), 12.7467 (10)</td></tr><tr><td>β (°)</td><td>98.523 (3)</td></tr><tr><td>V (Å<sup>3</sup>)</td><td>2641.7 (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>0.51</td></tr><tr><td>Crystal size (mm)</td><td>0.32 × 0.30 × 0.10</td></tr><tr><td>Data collection</td><td></td></tr><tr><td>Diffractometer</td><td>D8 VENTURE Bruker AXS</td></tr><tr><td>Absorption correction</td><td>Multi-scan (SADABS; Bruker, 2014)</td></tr><tr><td>T<sub>min</sub>, T<sub>max</sub></td><td>0.704, 0.950</td></tr><tr><td>No. of measured, independent and observed [I > 2σ(I)] reflections</td><td>28170, 12068, 9931</td></tr><tr><td>R<sub>int</sub></td><td>0.047</td></tr><tr><td>(sin θ/λ)<sub>max</sub> (Å<sup>-1</sup>)</td><td>0.650</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>0.051, 0.139, 1.04</td></tr><tr><td>No. of reflections</td><td>12068</td></tr><tr><td>No. of parameters</td><td>563</td></tr><tr><td>No. of restraints</td><td>1</td></tr><tr><td>H-atom treatment</td><td>H-atom parameters constrained</td></tr><tr><td>Δρ<sub>max</sub>, Δρ<sub>min</sub> (e Å<sup>-3</sup>)</td><td>0.43, -0.42</td></tr><tr><td>Absolute structure</td><td>Flack (1983)</td></tr><tr><td>Absolute structure parameter</td><td>0.033 (15)</td></tr></tbody></table>

Computer programs: SAINT (Bruker, 2014), APEX3 (Bruker, 2015), SIR97 (Altomare et al., 1999), SHELXL20183 (Sheldrick, 2015), SXGRAPH (Farrugia, 1999), Mercury (Macrae et al., 2008) and CRYSCALC (Roisnel, local program, 2019).

following the BYPASS algorithm (Sluis & Spek, 1990), implemented as the SQUEEZE option in PLATON (Spek, 2015). H atoms were finally included in their calculated positions (C–H = 0.95–0.98 Å) and refined as riding atoms with $U_{iso}(H) = 1.2U_{eq}(C)$ or $1.5U_{eq}(methyl C)$. The methyl H atoms

were allowed to rotate, but not to tip, to best fit the electron density. The crystal studied was refined as an inversion twin.

## References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). *J. Appl. Cryst.* **32**, 115–119.

Bruker (2014). *SAINT* and *SADABS*. Bruker AXS, Inc., Madison, Wisconsin, USA.

Bruker (2015). *APEX3*. Bruker AXS, Inc., Madison, Wisconsin, USA.

Carrie, D., Srour, H., Le Maux, P. & Simonneaux, G. (2016). *Tetrahedron Lett.* **57**, 1179–1182.

Chen, W. T., Yi, X. G., Luo, Z. G., Fu, H. R. & Liu, J. (2014). *Russ. J. Phys. Chem.* **88**, 1228–1231.

Farrugia, L. J. (1999). *J. Appl. Cryst.* **32**, 837–838.

Ferrand, Y., Le Maux, P. & Simonneaux, G. (2005). *Tetrahedron Asymmetry*, **16**, 3829–3836.

Flack, H. D. (1983). *Acta Cryst.* **A39**, 876–881.

Fleischer, E. B. & Shachter, A. M. (1991). *Inorg. Chem.* **30**, 3763–3769.

Galardon, E., Le Maux, P. & Simonneaux, G. (2000). *Tetrahedron*, **56**, 615–621.

Goodman, J. M., James, J. J. & Whiting, A. (1994). *J. Chem. Soc. Perkin Trans.* **2**, pp. 109–115.

Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). *J. Appl. Cryst.* **41**, 466–470.

Mix, K. A., Aronoff, M. R. & Raines, R. T. (2016). *Chem. Biol.* **11**, 3233–3244.

Nasri, S., Amiri, N., Turowska-Tyrk, I., Daran, J.-C. & Nasri, H. (2016). *Acta Cryst.* **E72**, 164–169.

Nicolas, I., Le Maux, P. & Simonneaux, G. (2008). *Tetrahedron Lett.* **49**, 5793–5795.

Nicolas, I., Roisnel, T., Le Maux, P. & Simonneaux, G. (2009). *Tetrahedron Lett.* **50**, 5149–5151.

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

Sluis, P. van der & Spek, A. L. (1990). *Acta Cryst.* **A46**, 194–201.

Spek, A. L. (2015). *Acta Cryst.* **C71**, 9–18.

Yanez, E. C., Arceo de la Pena, A., Muchowski, J. M. & Almanza, R. C. (2003). *Rev. Soc. Quim. Mex.* **47**, 202–206.

Ye, T. & McKervey, M. A. (1994). *Chem. Rev.* **94**, 1091–1160.
supporting information

Acta Cryst. (2020). E76, 273-275 [https://doi.org/10.1107/S2056989020001085]

# Crystal structure of {4-[10,15,20-tris(4-methoxyphenyl)porphyrin-5-yl]benzyl 2-diazoacetato}zinc(II)

Daniel Carrie, Thierry Roisnel and Gerard Simonneaux

## Computing details

Data collection: SAINT (Bruker, 2014); cell refinement: APEX3 (Bruker, 2015); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: SXGRAPH (Farrugia, 1999), Mercury (Macrae et al., 2008); software used to prepare material for publication: CRYSCALC (Roisnel, local program, 2019).

{4-[10,15,20-Tris(4-methoxyphenyl)porphyrin-5-yl]benzyl 2-diazoacetato}zinc(II)

## Crystal data

[Zn(C₅₀H₃₆N₆O₅)]

$M_r$ = 866.22

Monoclinic, P2₁

a = 10.8054 (8) Å

b = 19.3938 (14) Å

c = 12.7467 (10) Å

$\beta$ = 98.523 (3)°

$V$ = 2641.7 (3) Å³

$Z$ = 2

$F(000)$ = 896

$D_x$ = 1.089 Mg m⁻³

Mo Kα radiation, $\lambda$ = 0.71073 Å

Cell parameters from 9886 reflections

$\theta$ = 2.5–27.4°

$\mu$ = 0.51 mm⁻¹

$T$ = 150 K

Prism, red

0.32 × 0.30 × 0.10 mm

## Data collection

D8 VENTURE Bruker AXS
diffractometer

Radiation source: Incoatec microfocus sealed
tube

Multilayer monochromator

Detector resolution: 10.4167 pixels mm⁻¹

rotation images scans

Absorption correction: multi-scan
(SADABS; Bruker, 2014)

$T_{min}$ = 0.704, $T_{max}$ = 0.950

28170 measured reflections

12068 independent reflections

9931 reflections with $I > 2\sigma(I)$

$R_{int}$ = 0.047

$\theta_{max}$ = 27.5°, $\theta_{min}$ = 2.1°

$h$ = -14→13

$k$ = -24→25

$l$ = -16→16

## Refinement

Refinement on $F^2$

Least-squares matrix: full

$R[F^2 > 2\sigma(F^2)]$ = 0.051

$wR(F^2)$ = 0.139

$S$ = 1.04

12068 reflections

563 parameters

1 restraint

Primary atom site location: structure-invariant
direct methods

Secondary atom site location: difference Fourier
map

Hydrogen site location: inferred from
neighbouring sites

H-atom parameters constrained

$$w = 1/[\sigma^2(F_o^2) + (0.0738P)^2 + 1.1085P]$$
where $P = (F_o^2 + 2F_c^2)/3$
$$ (\Delta/\sigma)_{\max} = 0.024 $$

$$ \Delta\rho_{\max} = 0.43 \text{ e Å}^{-3} $$

$$ \Delta\rho_{\min} = -0.42 \text{ e Å}^{-3} $$

Absolute structure: Flack (1983)

Absolute structure parameter: 0.033 (15)

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.

**Refinement.** Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

<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>Zn1</td><td>0.00556 (5)</td><td>0.70060 (3)</td><td>0.62458 (4)</td><td>0.02718 (14)</td></tr><tr><td>N1</td><td>0.0900 (4)</td><td>0.7458 (2)</td><td>0.5081 (3)</td><td>0.0273 (9)</td></tr><tr><td>N2</td><td>-0.1436 (4)</td><td>0.6737 (2)</td><td>0.5139 (3)</td><td>0.0279 (9)</td></tr><tr><td>N3</td><td>-0.0613 (4)</td><td>0.6355 (2)</td><td>0.7323 (3)</td><td>0.0280 (9)</td></tr><tr><td>N4</td><td>0.1702 (3)</td><td>0.7083 (3)</td><td>0.7288 (3)</td><td>0.0264 (8)</td></tr><tr><td>C1</td><td>0.0353 (4)</td><td>0.7599 (3)</td><td>0.4074 (4)</td><td>0.0258 (10)</td></tr><tr><td>C2</td><td>-0.0846 (5)</td><td>0.7376 (3)</td><td>0.3602 (4)</td><td>0.0284 (10)</td></tr><tr><td>C3</td><td>-0.1656 (4)</td><td>0.6983 (3)</td><td>0.4102 (3)</td><td>0.0282 (9)</td></tr><tr><td>C4</td><td>-0.2887 (5)</td><td>0.6744 (3)</td><td>0.3615 (4)</td><td>0.0294 (10)</td></tr><tr><td>H4</td><td>-0.327042</td><td>0.683287</td><td>0.290868</td><td>0.035*</td></tr><tr><td>C5</td><td>-0.3383 (5)</td><td>0.6375 (3)</td><td>0.4341 (4)</td><td>0.0341 (12)</td></tr><tr><td>H5</td><td>-0.417616</td><td>0.615398</td><td>0.425012</td><td>0.041*</td></tr><tr><td>C6</td><td>-0.2463 (5)</td><td>0.6384 (3)</td><td>0.5294 (4)</td><td>0.0267 (10)</td></tr><tr><td>C7</td><td>-0.2652 (5)</td><td>0.6058 (2)</td><td>0.6254 (4)</td><td>0.0257 (10)</td></tr><tr><td>C8</td><td>-0.1758 (5)</td><td>0.6049 (3)</td><td>0.7185 (4)</td><td>0.0304 (11)</td></tr><tr><td>C9</td><td>-0.1968 (6)</td><td>0.5711 (3)</td><td>0.8157 (4)</td><td>0.0401 (13)</td></tr><tr><td>H9</td><td>-0.269308</td><td>0.546393</td><td>0.827774</td><td>0.048*</td></tr><tr><td>C10</td><td>-0.0913 (5)</td><td>0.5821 (3)</td><td>0.8860 (4)</td><td>0.0331 (12)</td></tr><tr><td>H10</td><td>-0.075922</td><td>0.565878</td><td>0.957105</td><td>0.040*</td></tr><tr><td>C11</td><td>-0.0068 (5)</td><td>0.6227 (3)</td><td>0.8337 (4)</td><td>0.0281 (10)</td></tr><tr><td>C12</td><td>0.1111 (5)</td><td>0.6462 (3)</td><td>0.8823 (4)</td><td>0.0309 (11)</td></tr><tr><td>C13</td><td>0.1928 (5)</td><td>0.6856 (2)</td><td>0.8307 (4)</td><td>0.0281 (11)</td></tr><tr><td>C14</td><td>0.3165 (5)</td><td>0.7062 (3)</td><td>0.8786 (4)</td><td>0.0345 (10)</td></tr><tr><td>H14</td><td>0.355695</td><td>0.696032</td><td>0.948623</td><td>0.041*</td></tr><tr><td>C15</td><td>0.3662 (5)</td><td>0.7428 (3)</td><td>0.8045 (4)</td><td>0.0327 (11)</td></tr><tr><td>H15</td><td>0.446606</td><td>0.763638</td><td>0.813239</td><td>0.039*</td></tr><tr><td>C16</td><td>0.2751 (4)</td><td>0.7442 (3)</td><td>0.7105 (4)</td><td>0.0266 (10)</td></tr><tr><td>C17</td><td>0.2948 (5)</td><td>0.7755 (2)</td><td>0.6138 (4)</td><td>0.0262 (10)</td></tr><tr><td>C18</td><td>0.2070 (5)</td><td>0.7756 (2)</td><td>0.5209 (4)</td><td>0.0263 (10)</td></tr><tr><td>C19</td><td>0.2248 (5)</td><td>0.8106 (3)</td><td>0.4230 (4)</td><td>0.0325 (11)</td></tr><tr><td>H19</td><td>0.296284</td><td>0.836265</td><td>0.410923</td><td>0.039*</td></tr><tr><td>C20</td><td>0.1203 (6)</td><td>0.7995 (3)</td><td>0.3528 (4)</td><td>0.0408 (13)</td></tr></tbody></table>
<table>
  <tr>
    <td>H20</td>
    <td>0.105179</td>
    <td>0.814796</td>
    <td>0.281241</td>
    <td>0.049*</td>
  </tr>
  <tr>
    <td>C21</td>
    <td>-0.1269 (5)</td>
    <td>0.7562 (3)</td>
    <td>0.2450 (4)</td>
    <td>0.0305 (11)</td>
  </tr>
  <tr>
    <td>C22</td>
    <td>-0.1727 (9)</td>
    <td>0.8212 (4)</td>
    <td>0.2161 (5)</td>
    <td>0.061 (2)</td>
  </tr>
  <tr>
    <td>H22</td>
    <td>-0.177863</td>
    <td>0.854917</td>
    <td>0.269352</td>
    <td>0.073*</td>
  </tr>
  <tr>
    <td>C23</td>
    <td>-0.2109 (9)</td>
    <td>0.8379 (4)</td>
    <td>0.1107 (6)</td>
    <td>0.067 (2)</td>
  </tr>
  <tr>
    <td>H23</td>
    <td>-0.236839</td>
    <td>0.883653</td>
    <td>0.092358</td>
    <td>0.080*</td>
  </tr>
  <tr>
    <td>C24</td>
    <td>-0.2119 (6)</td>
    <td>0.7893 (3)</td>
    <td>0.0320 (4)</td>
    <td>0.0434 (14)</td>
  </tr>
  <tr>
    <td>C25</td>
    <td>-0.1649 (6)</td>
    <td>0.7242 (3)</td>
    <td>0.0607 (5)</td>
    <td>0.0475 (16)</td>
  </tr>
  <tr>
    <td>H25</td>
    <td>-0.162430</td>
    <td>0.689600</td>
    <td>0.008378</td>
    <td>0.057*</td>
  </tr>
  <tr>
    <td>C26</td>
    <td>-0.1217 (5)</td>
    <td>0.7103 (3)</td>
    <td>0.1663 (4)</td>
    <td>0.0395 (13)</td>
  </tr>
  <tr>
    <td>H26</td>
    <td>-0.086674</td>
    <td>0.666223</td>
    <td>0.184301</td>
    <td>0.047*</td>
  </tr>
  <tr>
    <td>O27</td>
    <td>-0.2603 (5)</td>
    <td>0.8092 (3)</td>
    <td>-0.0664 (3)</td>
    <td>0.0585 (13)</td>
  </tr>
  <tr>
    <td>C28</td>
    <td>-0.2763 (7)</td>
    <td>0.7571 (4)</td>
    <td>-0.1445 (5)</td>
    <td>0.0555 (18)</td>
  </tr>
  <tr>
    <td>H28A</td>
    <td>-0.320784</td>
    <td>0.717971</td>
    <td>-0.118881</td>
    <td>0.083*</td>
  </tr>
  <tr>
    <td>H28B</td>
    <td>-0.194202</td>
    <td>0.741805</td>
    <td>-0.159425</td>
    <td>0.083*</td>
  </tr>
  <tr>
    <td>H28C</td>
    <td>-0.324992</td>
    <td>0.775327</td>
    <td>-0.209602</td>
    <td>0.083*</td>
  </tr>
  <tr>
    <td>C31</td>
    <td>0.1521 (5)</td>
    <td>0.6269 (3)</td>
    <td>0.9941 (4)</td>
    <td>0.0298 (10)</td>
  </tr>
  <tr>
    <td>C32</td>
    <td>0.1745 (6)</td>
    <td>0.5584 (3)</td>
    <td>1.0261 (5)</td>
    <td>0.0419 (13)</td>
  </tr>
  <tr>
    <td>H32</td>
    <td>0.160518</td>
    <td>0.522090</td>
    <td>0.975640</td>
    <td>0.050*</td>
  </tr>
  <tr>
    <td>C33</td>
    <td>0.2178 (6)</td>
    <td>0.5436 (3)</td>
    <td>1.1330 (4)</td>
    <td>0.0380 (12)</td>
  </tr>
  <tr>
    <td>H33</td>
    <td>0.231397</td>
    <td>0.496819</td>
    <td>1.153829</td>
    <td>0.046*</td>
  </tr>
  <tr>
    <td>C34</td>
    <td>0.2405 (6)</td>
    <td>0.5930 (3)</td>
    <td>1.2067 (5)</td>
    <td>0.0424 (14)</td>
  </tr>
  <tr>
    <td>C35</td>
    <td>0.2166 (6)</td>
    <td>0.6622 (3)</td>
    <td>1.1777 (4)</td>
    <td>0.0397 (13)</td>
  </tr>
  <tr>
    <td>H35</td>
    <td>0.229459</td>
    <td>0.697573</td>
    <td>1.229692</td>
    <td>0.048*</td>
  </tr>
  <tr>
    <td>C36</td>
    <td>0.1744 (5)</td>
    <td>0.6783 (3)</td>
    <td>1.0732 (4)</td>
    <td>0.0363 (12)</td>
  </tr>
  <tr>
    <td>H36</td>
    <td>0.159940</td>
    <td>0.725241</td>
    <td>1.053906</td>
    <td>0.044*</td>
  </tr>
  <tr>
    <td>O37</td>
    <td>0.2872 (4)</td>
    <td>0.5733 (2)</td>
    <td>1.3082 (3)</td>
    <td>0.0470 (10)</td>
  </tr>
  <tr>
    <td>C38</td>
    <td>0.3071 (7)</td>
    <td>0.6249 (3)</td>
    <td>1.3886 (5)</td>
    <td>0.0478 (15)</td>
  </tr>
  <tr>
    <td>H38A</td>
    <td>0.363013</td>
    <td>0.660543</td>
    <td>1.367831</td>
    <td>0.072*</td>
  </tr>
  <tr>
    <td>H38B</td>
    <td>0.345083</td>
    <td>0.603894</td>
    <td>1.455623</td>
    <td>0.072*</td>
  </tr>
  <tr>
    <td>H38C</td>
    <td>0.226739</td>
    <td>0.645802</td>
    <td>1.397698</td>
    <td>0.072*</td>
  </tr>
  <tr>
    <td>C41</td>
    <td>-0.3889 (5)</td>
    <td>0.5724 (2)</td>
    <td>0.6304 (4)</td>
    <td>0.0260 (10)</td>
  </tr>
  <tr>
    <td>C42</td>
    <td>-0.4812 (6)</td>
    <td>0.6063 (3)</td>
    <td>0.6729 (5)</td>
    <td>0.0387 (13)</td>
  </tr>
  <tr>
    <td>H42</td>
    <td>-0.465968</td>
    <td>0.652103</td>
    <td>0.697849</td>
    <td>0.046*</td>
  </tr>
  <tr>
    <td>C43</td>
    <td>-0.5957 (6)</td>
    <td>0.5764 (3)</td>
    <td>0.6808 (6)</td>
    <td>0.0464 (15)</td>
  </tr>
  <tr>
    <td>H43</td>
    <td>-0.658937</td>
    <td>0.602078</td>
    <td>0.707695</td>
    <td>0.056*</td>
  </tr>
  <tr>
    <td>C44</td>
    <td>-0.6171 (5)</td>
    <td>0.5084 (3)</td>
    <td>0.6488 (5)</td>
    <td>0.0353 (12)</td>
  </tr>
  <tr>
    <td>C45</td>
    <td>-0.5207 (7)</td>
    <td>0.4725 (3)</td>
    <td>0.6066 (5)</td>
    <td>0.0497 (16)</td>
  </tr>
  <tr>
    <td>H45</td>
    <td>-0.532431</td>
    <td>0.425747</td>
    <td>0.585217</td>
    <td>0.060*</td>
  </tr>
  <tr>
    <td>C46</td>
    <td>-0.4128 (6)</td>
    <td>0.5049 (3)</td>
    <td>0.5969 (6)</td>
    <td>0.0454 (15)</td>
  </tr>
  <tr>
    <td>H46</td>
    <td>-0.350744</td>
    <td>0.480710</td>
    <td>0.566033</td>
    <td>0.054*</td>
  </tr>
  <tr>
    <td>O47</td>
    <td>-0.7270 (4)</td>
    <td>0.4728 (2)</td>
    <td>0.6512 (5)</td>
    <td>0.0628 (14)</td>
  </tr>
  <tr>
    <td>C48</td>
    <td>-0.8253 (10)</td>
    <td>0.5098 (5)</td>
    <td>0.6903 (13)</td>
    <td>0.123 (5)</td>
  </tr>
  <tr>
    <td>H48A</td>
    <td>-0.827708</td>
    <td>0.557236</td>
    <td>0.663782</td>
    <td>0.184*</td>
  </tr>
  <tr>
    <td>H48B</td>
    <td>-0.809986</td>
    <td>0.510177</td>
    <td>0.768063</td>
    <td>0.184*</td>
  </tr>
  <tr>
    <td>H48C</td>
    <td>-0.905543</td>
    <td>0.487177</td>
    <td>0.665944</td>
    <td>0.184*</td>
  </tr>
  <tr>
    <td>C54</td>
    <td>0.6527 (5)</td>
    <td>0.8721 (3)</td>
    <td>0.6153 (4)</td>
    <td>0.0297 (11)</td>
  </tr>
  <tr>
    <td>C55</td>
    <td>0.5618 (5)</td>
    <td>0.9019 (3)</td>
    <td>0.6678 (5)</td>
    <td>0.0357 (12)</td>
  </tr>
</table>
<table><tr><td>H55</td><td>0.579464</td><td>0.944167</td><td>0.704745</td><td>0.043*</td></tr><tr><td>C56</td><td>0.4463 (6)</td><td>0.8711 (3)</td><td>0.6671 (5)</td><td>0.0385 (13)</td></tr><tr><td>H56</td><td>0.386237</td><td>0.892012</td><td>0.704379</td><td>0.046*</td></tr><tr><td>C51</td><td>0.4173 (5)</td><td>0.8096 (3)</td><td>0.6121 (4)</td><td>0.0271 (10)</td></tr><tr><td>C52</td><td>0.5070 (5)</td><td>0.7809 (2)</td><td>0.5572 (4)</td><td>0.0256 (10)</td></tr><tr><td>H52</td><td>0.488255</td><td>0.739651</td><td>0.517825</td><td>0.031*</td></tr><tr><td>C53</td><td>0.6239 (5)</td><td>0.8117 (3)</td><td>0.5589 (4)</td><td>0.0306 (11)</td></tr><tr><td>H53</td><td>0.684042</td><td>0.791255</td><td>0.521289</td><td>0.037*</td></tr><tr><td>O58</td><td>0.8581 (4)</td><td>0.89908 (19)</td><td>0.7153 (3)</td><td>0.0390 (9)</td></tr><tr><td>C59</td><td>0.9262 (5)</td><td>0.8416 (3)</td><td>0.7264 (5)</td><td>0.0342 (12)</td></tr><tr><td>C57</td><td>0.7751 (5)</td><td>0.9070 (3)</td><td>0.6121 (4)</td><td>0.0326 (11)</td></tr><tr><td>H57A</td><td>0.816041</td><td>0.886703</td><td>0.554810</td><td>0.039*</td></tr><tr><td>H57B</td><td>0.760818</td><td>0.956611</td><td>0.596421</td><td>0.039*</td></tr><tr><td>O60</td><td>0.9171 (4)</td><td>0.7974 (2)</td><td>0.6583 (3)</td><td>0.0410 (9)</td></tr><tr><td>C61</td><td>1.0062 (7)</td><td>0.8346 (3)</td><td>0.8270 (6)</td><td>0.0530 (18)</td></tr><tr><td>H61</td><td>1.059875</td><td>0.795791</td><td>0.839911</td><td>0.064*</td></tr><tr><td>N62</td><td>1.0053 (7)</td><td>0.8808 (4)</td><td>0.8992 (6)</td><td>0.076 (2)</td></tr><tr><td>N63</td><td>1.0095 (9)</td><td>0.9222 (5)</td><td>0.9599 (7)</td><td>0.109 (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>Zn1</td><td>0.0255 (2)</td><td>0.0322 (3)</td><td>0.0238 (2)</td><td>-0.0034 (3)</td><td>0.00351 (18)</td><td>0.0022 (3)</td></tr><tr><td>N1</td><td>0.022 (2)</td><td>0.033 (2)</td><td>0.027 (2)</td><td>-0.0035 (17)</td><td>0.0065 (17)</td><td>0.0021 (17)</td></tr><tr><td>N2</td><td>0.031 (2)</td><td>0.033 (2)</td><td>0.019 (2)</td><td>-0.0007 (17)</td><td>0.0022 (17)</td><td>-0.0004 (16)</td></tr><tr><td>N3</td><td>0.027 (2)</td><td>0.031 (2)</td><td>0.024 (2)</td><td>-0.0103 (17)</td><td>0.0004 (17)</td><td>0.0036 (17)</td></tr><tr><td>N4</td><td>0.0224 (17)</td><td>0.031 (2)</td><td>0.0257 (18)</td><td>0.0005 (19)</td><td>0.0030 (14)</td><td>0.0083 (19)</td></tr><tr><td>C1</td><td>0.020 (2)</td><td>0.036 (3)</td><td>0.022 (2)</td><td>0.0022 (19)</td><td>0.0038 (18)</td><td>0.0054 (19)</td></tr><tr><td>C2</td><td>0.028 (2)</td><td>0.032 (2)</td><td>0.025 (2)</td><td>0.000 (2)</td><td>0.0030 (19)</td><td>0.001 (2)</td></tr><tr><td>C3</td><td>0.029 (2)</td><td>0.034 (2)</td><td>0.020 (2)</td><td>0.004 (3)</td><td>-0.0003 (16)</td><td>0.000 (2)</td></tr><tr><td>C4</td><td>0.025 (2)</td><td>0.039 (2)</td><td>0.023 (2)</td><td>-0.004 (2)</td><td>-0.0003 (19)</td><td>-0.001 (2)</td></tr><tr><td>C5</td><td>0.029 (3)</td><td>0.045 (3)</td><td>0.028 (3)</td><td>-0.001 (2)</td><td>0.005 (2)</td><td>-0.005 (2)</td></tr><tr><td>C6</td><td>0.029 (3)</td><td>0.031 (2)</td><td>0.021 (2)</td><td>0.000 (2)</td><td>0.0030 (19)</td><td>-0.0022 (18)</td></tr><tr><td>C7</td><td>0.029 (3)</td><td>0.027 (2)</td><td>0.023 (2)</td><td>-0.0018 (19)</td><td>0.0078 (19)</td><td>-0.0022 (18)</td></tr><tr><td>C8</td><td>0.036 (3)</td><td>0.034 (3)</td><td>0.022 (2)</td><td>-0.006 (2)</td><td>0.004 (2)</td><td>0.0011 (19)</td></tr><tr><td>C9</td><td>0.038 (3)</td><td>0.055 (3)</td><td>0.027 (3)</td><td>-0.016 (3)</td><td>0.002 (2)</td><td>0.008 (2)</td></tr><tr><td>C10</td><td>0.028 (3)</td><td>0.048 (3)</td><td>0.023 (3)</td><td>-0.011 (2)</td><td>0.001 (2)</td><td>0.010 (2)</td></tr><tr><td>C11</td><td>0.028 (3)</td><td>0.030 (2)</td><td>0.026 (2)</td><td>-0.005 (2)</td><td>0.004 (2)</td><td>0.0047 (19)</td></tr><tr><td>C12</td><td>0.029 (3)</td><td>0.038 (3)</td><td>0.024 (2)</td><td>0.001 (2)</td><td>-0.002 (2)</td><td>0.006 (2)</td></tr><tr><td>C13</td><td>0.025 (2)</td><td>0.032 (3)</td><td>0.028 (2)</td><td>-0.0006 (18)</td><td>0.0061 (19)</td><td>0.0038 (17)</td></tr><tr><td>C14</td><td>0.031 (2)</td><td>0.042 (3)</td><td>0.030 (2)</td><td>-0.004 (3)</td><td>0.0008 (18)</td><td>0.004 (3)</td></tr><tr><td>C15</td><td>0.026 (3)</td><td>0.042 (3)</td><td>0.029 (3)</td><td>-0.008 (2)</td><td>0.001 (2)</td><td>0.004 (2)</td></tr><tr><td>C16</td><td>0.020 (2)</td><td>0.032 (2)</td><td>0.029 (2)</td><td>-0.0027 (19)</td><td>0.0053 (19)</td><td>0.0004 (19)</td></tr><tr><td>C17</td><td>0.026 (2)</td><td>0.024 (2)</td><td>0.029 (3)</td><td>-0.0067 (18)</td><td>0.003 (2)</td><td>-0.0015 (18)</td></tr><tr><td>C18</td><td>0.026 (2)</td><td>0.031 (2)</td><td>0.022 (2)</td><td>-0.0014 (19)</td><td>0.0065 (19)</td><td>0.0029 (18)</td></tr><tr><td>C19</td><td>0.031 (3)</td><td>0.041 (3)</td><td>0.025 (3)</td><td>-0.010 (2)</td><td>0.003 (2)</td><td>0.005 (2)</td></tr><tr><td>C20</td><td>0.049 (3)</td><td>0.051 (3)</td><td>0.023 (3)</td><td>0.002 (3)</td><td>0.008 (2)</td><td>0.012 (2)</td></tr><tr><td>C21</td><td>0.028 (3)</td><td>0.039 (3)</td><td>0.025 (3)</td><td>0.000 (2)</td><td>0.005 (2)</td><td>0.006 (2)</td></tr></tbody></table>
<table><tr><td>C22</td><td>0.103 (6)</td><td>0.042 (3)</td><td>0.036 (3)</td><td>0.013 (4)</td><td>0.006 (4)</td><td>0.006 (3)</td></tr><tr><td>C23</td><td>0.102 (7)</td><td>0.043 (4)</td><td>0.049 (4)</td><td>0.018 (4)</td><td>-0.006 (4)</td><td>0.005 (3)</td></tr><tr><td>C24</td><td>0.046 (3)</td><td>0.060 (4)</td><td>0.025 (3)</td><td>0.005 (3)</td><td>0.010 (2)</td><td>0.019 (3)</td></tr><tr><td>C25</td><td>0.051 (4)</td><td>0.062 (4)</td><td>0.029 (3)</td><td>0.014 (3)</td><td>0.006 (3)</td><td>0.001 (2)</td></tr><tr><td>C26</td><td>0.044 (3)</td><td>0.038 (3)</td><td>0.035 (3)</td><td>0.017 (3)</td><td>-0.001 (2)</td><td>0.004 (2)</td></tr><tr><td>O27</td><td>0.065 (3)</td><td>0.079 (3)</td><td>0.029 (2)</td><td>0.018 (3)</td><td>0.002 (2)</td><td>0.012 (2)</td></tr><tr><td>C28</td><td>0.058 (4)</td><td>0.080 (5)</td><td>0.025 (3)</td><td>-0.002 (4)</td><td>-0.004 (3)</td><td>0.017 (3)</td></tr><tr><td>C31</td><td>0.028 (3)</td><td>0.034 (2)</td><td>0.027 (3)</td><td>-0.004 (2)</td><td>0.002 (2)</td><td>-0.001 (2)</td></tr><tr><td>C32</td><td>0.049 (3)</td><td>0.041 (3)</td><td>0.032 (3)</td><td>-0.002 (3)</td><td>-0.003 (3)</td><td>0.008 (2)</td></tr><tr><td>C33</td><td>0.052 (3)</td><td>0.033 (3)</td><td>0.029 (3)</td><td>-0.005 (2)</td><td>0.002 (2)</td><td>0.007 (2)</td></tr><tr><td>C34</td><td>0.040 (3)</td><td>0.054 (4)</td><td>0.030 (3)</td><td>-0.007 (3)</td><td>-0.003 (2)</td><td>0.009 (3)</td></tr><tr><td>C35</td><td>0.039 (3)</td><td>0.055 (3)</td><td>0.024 (3)</td><td>-0.008 (3)</td><td>0.001 (2)</td><td>-0.003 (2)</td></tr><tr><td>C36</td><td>0.037 (3)</td><td>0.042 (3)</td><td>0.029 (3)</td><td>0.001 (2)</td><td>0.000 (2)</td><td>0.006 (2)</td></tr><tr><td>O37</td><td>0.057 (3)</td><td>0.046 (2)</td><td>0.035 (2)</td><td>0.000 (2)</td><td>-0.002 (2)</td><td>0.0109 (18)</td></tr><tr><td>C38</td><td>0.048 (4)</td><td>0.048 (3)</td><td>0.043 (4)</td><td>-0.002 (3)</td><td>-0.009 (3)</td><td>-0.002 (3)</td></tr><tr><td>C41</td><td>0.030 (3)</td><td>0.027 (2)</td><td>0.021 (2)</td><td>-0.004 (2)</td><td>0.0042 (19)</td><td>-0.0008 (18)</td></tr><tr><td>C42</td><td>0.041 (3)</td><td>0.029 (3)</td><td>0.050 (4)</td><td>-0.008 (2)</td><td>0.017 (3)</td><td>-0.004 (2)</td></tr><tr><td>C43</td><td>0.032 (3)</td><td>0.039 (3)</td><td>0.072 (5)</td><td>-0.004 (2)</td><td>0.018 (3)</td><td>-0.004 (3)</td></tr><tr><td>C44</td><td>0.034 (3)</td><td>0.026 (2)</td><td>0.045 (3)</td><td>-0.013 (2)</td><td>0.005 (2)</td><td>0.004 (2)</td></tr><tr><td>C45</td><td>0.059 (4)</td><td>0.037 (3)</td><td>0.056 (4)</td><td>-0.017 (3)</td><td>0.018 (3)</td><td>-0.016 (3)</td></tr><tr><td>C46</td><td>0.037 (3)</td><td>0.042 (3)</td><td>0.059 (4)</td><td>-0.005 (3)</td><td>0.015 (3)</td><td>-0.019 (3)</td></tr><tr><td>O47</td><td>0.038 (2)</td><td>0.047 (2)</td><td>0.108 (4)</td><td>-0.015 (2)</td><td>0.025 (3)</td><td>-0.004 (3)</td></tr><tr><td>C48</td><td>0.079 (7)</td><td>0.052 (5)</td><td>0.259 (17)</td><td>-0.015 (5)</td><td>0.096 (9)</td><td>-0.032 (7)</td></tr><tr><td>C54</td><td>0.030 (3)</td><td>0.023 (2)</td><td>0.036 (3)</td><td>0.003 (2)</td><td>0.006 (2)</td><td>0.008 (2)</td></tr><tr><td>C55</td><td>0.036 (3)</td><td>0.033 (3)</td><td>0.039 (3)</td><td>-0.006 (2)</td><td>0.011 (2)</td><td>-0.013 (2)</td></tr><tr><td>C56</td><td>0.043 (3)</td><td>0.031 (3)</td><td>0.044 (3)</td><td>-0.003 (2)</td><td>0.015 (3)</td><td>-0.014 (2)</td></tr><tr><td>C51</td><td>0.024 (2)</td><td>0.034 (2)</td><td>0.022 (2)</td><td>-0.002 (2)</td><td>0.0009 (19)</td><td>-0.0019 (19)</td></tr><tr><td>C52</td><td>0.024 (2)</td><td>0.028 (2)</td><td>0.024 (2)</td><td>-0.0025 (19)</td><td>0.0008 (19)</td><td>-0.0022 (18)</td></tr><tr><td>C53</td><td>0.031 (3)</td><td>0.030 (2)</td><td>0.031 (3)</td><td>0.001 (2)</td><td>0.006 (2)</td><td>0.007 (2)</td></tr><tr><td>O58</td><td>0.041 (2)</td><td>0.0315 (19)</td><td>0.043 (2)</td><td>-0.0015 (16)</td><td>0.0017 (18)</td><td>-0.0020 (16)</td></tr><tr><td>C59</td><td>0.028 (3)</td><td>0.027 (2)</td><td>0.050 (3)</td><td>-0.003 (2)</td><td>0.015 (2)</td><td>-0.007 (2)</td></tr><tr><td>C57</td><td>0.026 (3)</td><td>0.032 (2)</td><td>0.040 (3)</td><td>-0.004 (2)</td><td>0.005 (2)</td><td>0.001 (2)</td></tr><tr><td>O60</td><td>0.044 (2)</td><td>0.037 (2)</td><td>0.042 (2)</td><td>0.0002 (17)</td><td>0.0075 (18)</td><td>-0.0055 (17)</td></tr><tr><td>C61</td><td>0.055 (4)</td><td>0.033 (3)</td><td>0.063 (4)</td><td>0.002 (3)</td><td>-0.017 (3)</td><td>-0.014 (3)</td></tr><tr><td>N62</td><td>0.079 (5)</td><td>0.080 (5)</td><td>0.066 (4)</td><td>0.030 (4)</td><td>0.001 (4)</td><td>-0.014 (4)</td></tr><tr><td>N63</td><td>0.109 (7)</td><td>0.118 (7)</td><td>0.089 (6)</td><td>0.034 (6)</td><td>-0.021 (5)</td><td>-0.066 (6)</td></tr></table>

Geometric parameters (Å, °)

<table><tr><td>Zn1—N2</td><td>2.046 (4)</td><td>C26—H26</td><td>0.9500</td></tr><tr><td>Zn1—N1</td><td>2.051 (4)</td><td>O27—C28</td><td>1.411 (9)</td></tr><tr><td>Zn1—N4</td><td>2.062 (4)</td><td>C28—H28A</td><td>0.9800</td></tr><tr><td>Zn1—N3</td><td>2.073 (4)</td><td>C28—H28B</td><td>0.9800</td></tr><tr><td>Zn1—O60<sup>i</sup></td><td>2.179 (4)</td><td>C28—H28C</td><td>0.9800</td></tr><tr><td>N1—C1</td><td>1.359 (6)</td><td>C31—C32</td><td>1.401 (8)</td></tr><tr><td>N1—C18</td><td>1.378 (6)</td><td>C31—C36</td><td>1.413 (8)</td></tr><tr><td>N2—C6</td><td>1.343 (7)</td><td>C32—C33</td><td>1.403 (8)</td></tr><tr><td>N2—C3</td><td>1.392 (6)</td><td>C32—H32</td><td>0.9500</td></tr></table>
<table>
  <tr>
    <td>N3—C8</td>
    <td>1.359 (7)</td>
    <td>C33—C34</td>
    <td>1.340 (8)</td>
  </tr>
  <tr>
    <td>N3—C11</td>
    <td>1.360 (7)</td>
    <td>C33—H33</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>N4—C13</td>
    <td>1.359 (6)</td>
    <td>C34—O37</td>
    <td>1.371 (7)</td>
  </tr>
  <tr>
    <td>N4—C16</td>
    <td>1.379 (6)</td>
    <td>C34—C35</td>
    <td>1.405 (9)</td>
  </tr>
  <tr>
    <td>C1—C2</td>
    <td>1.413 (7)</td>
    <td>C35—C36</td>
    <td>1.378 (8)</td>
  </tr>
  <tr>
    <td>C1—C20</td>
    <td>1.452 (7)</td>
    <td>C35—H35</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>C2—C3</td>
    <td>1.385 (7)</td>
    <td>C36—H36</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>C2—C21</td>
    <td>1.517 (7)</td>
    <td>O37—C38</td>
    <td>1.426 (8)</td>
  </tr>
  <tr>
    <td>C3—C4</td>
    <td>1.457 (7)</td>
    <td>C38—H38A</td>
    <td>0.9800</td>
  </tr>
  <tr>
    <td>C4—C5</td>
    <td>1.342 (8)</td>
    <td>C38—H38B</td>
    <td>0.9800</td>
  </tr>
  <tr>
    <td>C4—H4</td>
    <td>0.9500</td>
    <td>C38—H38C</td>
    <td>0.9800</td>
  </tr>
  <tr>
    <td>C5—C6</td>
    <td>1.451 (7)</td>
    <td>C41—C42</td>
    <td>1.372 (8)</td>
  </tr>
  <tr>
    <td>C5—H5</td>
    <td>0.9500</td>
    <td>C41—C46</td>
    <td>1.389 (8)</td>
  </tr>
  <tr>
    <td>C6—C7</td>
    <td>1.419 (7)</td>
    <td>C42—C43</td>
    <td>1.383 (8)</td>
  </tr>
  <tr>
    <td>C7—C8</td>
    <td>1.415 (7)</td>
    <td>C42—H42</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>C7—C41</td>
    <td>1.495 (7)</td>
    <td>C43—C44</td>
    <td>1.390 (8)</td>
  </tr>
  <tr>
    <td>C8—C9</td>
    <td>1.449 (7)</td>
    <td>C43—H43</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>C9—C10</td>
    <td>1.358 (8)</td>
    <td>C44—O47</td>
    <td>1.377 (7)</td>
  </tr>
  <tr>
    <td>C9—H9</td>
    <td>0.9500</td>
    <td>C44—C45</td>
    <td>1.423 (9)</td>
  </tr>
  <tr>
    <td>C10—C11</td>
    <td>1.443 (7)</td>
    <td>C45—C46</td>
    <td>1.345 (9)</td>
  </tr>
  <tr>
    <td>C10—H10</td>
    <td>0.9500</td>
    <td>C45—H45</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>C11—C12</td>
    <td>1.407 (7)</td>
    <td>C46—H46</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>C12—C13</td>
    <td>1.403 (7)</td>
    <td>O47—C48</td>
    <td>1.431 (10)</td>
  </tr>
  <tr>
    <td>C12—C31</td>
    <td>1.476 (7)</td>
    <td>C48—H48A</td>
    <td>0.9800</td>
  </tr>
  <tr>
    <td>C13—C14</td>
    <td>1.441 (7)</td>
    <td>C48—H48B</td>
    <td>0.9800</td>
  </tr>
  <tr>
    <td>C14—C15</td>
    <td>1.354 (7)</td>
    <td>C48—H48C</td>
    <td>0.9800</td>
  </tr>
  <tr>
    <td>C14—H14</td>
    <td>0.9500</td>
    <td>C54—C53</td>
    <td>1.384 (7)</td>
  </tr>
  <tr>
    <td>C15—C16</td>
    <td>1.434 (7)</td>
    <td>C54—C55</td>
    <td>1.394 (8)</td>
  </tr>
  <tr>
    <td>C15—H15</td>
    <td>0.9500</td>
    <td>C54—C57</td>
    <td>1.492 (7)</td>
  </tr>
  <tr>
    <td>C16—C17</td>
    <td>1.418 (7)</td>
    <td>C55—C56</td>
    <td>1.381 (8)</td>
  </tr>
  <tr>
    <td>C17—C18</td>
    <td>1.404 (7)</td>
    <td>C55—H55</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>C17—C51</td>
    <td>1.483 (7)</td>
    <td>C56—C51</td>
    <td>1.397 (7)</td>
  </tr>
  <tr>
    <td>C18—C19</td>
    <td>1.458 (7)</td>
    <td>C56—H56</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>C19—C20</td>
    <td>1.350 (8)</td>
    <td>C51—C52</td>
    <td>1.393 (7)</td>
  </tr>
  <tr>
    <td>C19—H19</td>
    <td>0.9500</td>
    <td>C52—C53</td>
    <td>1.395 (7)</td>
  </tr>
  <tr>
    <td>C20—H20</td>
    <td>0.9500</td>
    <td>C52—H52</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>C21—C26</td>
    <td>1.347 (8)</td>
    <td>C53—H53</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>C21—C22</td>
    <td>1.384 (8)</td>
    <td>O58—C59</td>
    <td>1.332 (6)</td>
  </tr>
  <tr>
    <td>C22—C23</td>
    <td>1.384 (10)</td>
    <td>O58—C57</td>
    <td>1.486 (7)</td>
  </tr>
  <tr>
    <td>C22—H22</td>
    <td>0.9500</td>
    <td>C59—O60</td>
    <td>1.213 (6)</td>
  </tr>
  <tr>
    <td>C23—C24</td>
    <td>1.374 (10)</td>
    <td>C59—C61</td>
    <td>1.443 (9)</td>
  </tr>
  <tr>
    <td>C23—H23</td>
    <td>0.9500</td>
    <td>C57—H57A</td>
    <td>0.9900</td>
  </tr>
  <tr>
    <td>C24—O27</td>
    <td>1.342 (7)</td>
    <td>C57—H57B</td>
    <td>0.9900</td>
  </tr>
  <tr>
    <td>C24—C25</td>
    <td>1.389 (9)</td>
    <td>C61—N62</td>
    <td>1.285 (10)</td>
  </tr>
  <tr>
    <td>C25—C26</td>
    <td>1.385 (8)</td>
    <td>C61—H61</td>
    <td>0.9500</td>
  </tr>
  <tr>
    <td>C25—H25</td>
    <td>0.9500</td>
    <td>N62—N63</td>
    <td>1.112 (10)</td>
  </tr>
  <tr>
    <td>N2—Zn1—N1</td>
    <td>89.95 (17)</td>
    <td>C26—C25—H25</td>
    <td>120.3</td>
  </tr>
</table>
<table>
  <tr>
    <td>N2—Zn1—N4</td>
    <td>168.25 (18)</td>
  </tr>
  <tr>
    <td>N1—Zn1—N4</td>
    <td>90.10 (16)</td>
  </tr>
  <tr>
    <td>N2—Zn1—N3</td>
    <td>89.15 (16)</td>
  </tr>
  <tr>
    <td>N1—Zn1—N3</td>
    <td>167.43 (17)</td>
  </tr>
  <tr>
    <td>N4—Zn1—N3</td>
    <td>88.25 (16)</td>
  </tr>
  <tr>
    <td>N2—Zn1—O60<sup>i</sup></td>
    <td>91.84 (16)</td>
  </tr>
  <tr>
    <td>N1—Zn1—O60<sup>i</sup></td>
    <td>91.71 (16)</td>
  </tr>
  <tr>
    <td>N4—Zn1—O60<sup>i</sup></td>
    <td>99.90 (17)</td>
  </tr>
  <tr>
    <td>N3—Zn1—O60<sup>i</sup></td>
    <td>100.85 (17)</td>
  </tr>
  <tr>
    <td>C1—N1—C18</td>
    <td>106.9 (4)</td>
  </tr>
  <tr>
    <td>C1—N1—Zn1</td>
    <td>126.3 (3)</td>
  </tr>
  <tr>
    <td>C18—N1—Zn1</td>
    <td>126.3 (3)</td>
  </tr>
  <tr>
    <td>C6—N2—C3</td>
    <td>106.6 (4)</td>
  </tr>
  <tr>
    <td>C6—N2—Zn1</td>
    <td>127.7 (3)</td>
  </tr>
  <tr>
    <td>C3—N2—Zn1</td>
    <td>125.0 (3)</td>
  </tr>
  <tr>
    <td>C8—N3—C11</td>
    <td>107.5 (4)</td>
  </tr>
  <tr>
    <td>C8—N3—Zn1</td>
    <td>125.4 (3)</td>
  </tr>
  <tr>
    <td>C11—N3—Zn1</td>
    <td>126.5 (3)</td>
  </tr>
  <tr>
    <td>C13—N4—C16</td>
    <td>106.8 (4)</td>
  </tr>
  <tr>
    <td>C13—N4—Zn1</td>
    <td>127.5 (3)</td>
  </tr>
  <tr>
    <td>C16—N4—Zn1</td>
    <td>125.5 (3)</td>
  </tr>
  <tr>
    <td>N1—C1—C2</td>
    <td>125.7 (4)</td>
  </tr>
  <tr>
    <td>N1—C1—C20</td>
    <td>110.0 (4)</td>
  </tr>
  <tr>
    <td>C2—C1—C20</td>
    <td>124.3 (5)</td>
  </tr>
  <tr>
    <td>C3—C2—C1</td>
    <td>125.1 (5)</td>
  </tr>
  <tr>
    <td>C3—C2—C21</td>
    <td>117.1 (4)</td>
  </tr>
  <tr>
    <td>C1—C2—C21</td>
    <td>117.7 (4)</td>
  </tr>
  <tr>
    <td>C2—C3—N2</td>
    <td>126.5 (4)</td>
  </tr>
  <tr>
    <td>C2—C3—C4</td>
    <td>125.4 (4)</td>
  </tr>
  <tr>
    <td>N2—C3—C4</td>
    <td>108.2 (4)</td>
  </tr>
  <tr>
    <td>C5—C4—C3</td>
    <td>108.0 (5)</td>
  </tr>
  <tr>
    <td>C5—C4—H4</td>
    <td>126.0</td>
  </tr>
  <tr>
    <td>C3—C4—H4</td>
    <td>126.0</td>
  </tr>
  <tr>
    <td>C4—C5—C6</td>
    <td>106.1 (5)</td>
  </tr>
  <tr>
    <td>C4—C5—H5</td>
    <td>127.0</td>
  </tr>
  <tr>
    <td>C6—C5—H5</td>
    <td>127.0</td>
  </tr>
  <tr>
    <td>N2—C6—C7</td>
    <td>125.6 (4)</td>
  </tr>
  <tr>
    <td>N2—C6—C5</td>
    <td>111.2 (4)</td>
  </tr>
  <tr>
    <td>C7—C6—C5</td>
    <td>123.3 (5)</td>
  </tr>
  <tr>
    <td>C8—C7—C6</td>
    <td>124.2 (5)</td>
  </tr>
  <tr>
    <td>C8—C7—C41</td>
    <td>117.6 (4)</td>
  </tr>
  <tr>
    <td>C6—C7—C41</td>
    <td>118.2 (4)</td>
  </tr>
  <tr>
    <td>N3—C8—C7</td>
    <td>126.8 (4)</td>
  </tr>
  <tr>
    <td>N3—C8—C9</td>
    <td>110.0 (5)</td>
  </tr>
  <tr>
    <td>C7—C8—C9</td>
    <td>123.3 (5)</td>
  </tr>
  <tr>
    <td>C10—C9—C8</td>
    <td>105.7 (5)</td>
  </tr>
  <tr>
    <td>C10—C9—H9</td>
    <td>127.2</td>
  </tr>
  <tr>
    <td>C8—C9—H9</td>
    <td>127.2</td>
  </tr>
</table>

<table>
  <tr>
    <td>C24—C25—H25</td>
    <td>120.3</td>
  </tr>
  <tr>
    <td>C21—C26—C25</td>
    <td>123.3 (5)</td>
  </tr>
  <tr>
    <td>C21—C26—H26</td>
    <td>118.3</td>
  </tr>
  <tr>
    <td>C25—C26—H26</td>
    <td>118.3</td>
  </tr>
  <tr>
    <td>C24—O27—C28</td>
    <td>116.4 (5)</td>
  </tr>
  <tr>
    <td>O27—C28—H28A</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>O27—C28—H28B</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H28A—C28—H28B</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>O27—C28—H28C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H28A—C28—H28C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H28B—C28—H28C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>C32—C31—C36</td>
    <td>117.2 (5)</td>
  </tr>
  <tr>
    <td>C32—C31—C12</td>
    <td>122.4 (5)</td>
  </tr>
  <tr>
    <td>C36—C31—C12</td>
    <td>120.4 (5)</td>
  </tr>
  <tr>
    <td>C31—C32—C33</td>
    <td>119.7 (5)</td>
  </tr>
  <tr>
    <td>C31—C32—H32</td>
    <td>120.2</td>
  </tr>
  <tr>
    <td>C33—C32—H32</td>
    <td>120.2</td>
  </tr>
  <tr>
    <td>C34—C33—C32</td>
    <td>122.3 (5)</td>
  </tr>
  <tr>
    <td>C34—C33—H33</td>
    <td>118.8</td>
  </tr>
  <tr>
    <td>C32—C33—H33</td>
    <td>118.8</td>
  </tr>
  <tr>
    <td>C33—C34—O37</td>
    <td>117.8 (5)</td>
  </tr>
  <tr>
    <td>C33—C34—C35</td>
    <td>119.4 (5)</td>
  </tr>
  <tr>
    <td>O37—C34—C35</td>
    <td>122.8 (6)</td>
  </tr>
  <tr>
    <td>C36—C35—C34</td>
    <td>119.5 (5)</td>
  </tr>
  <tr>
    <td>C36—C35—H35</td>
    <td>120.2</td>
  </tr>
  <tr>
    <td>C34—C35—H35</td>
    <td>120.2</td>
  </tr>
  <tr>
    <td>C35—C36—C31</td>
    <td>121.8 (5)</td>
  </tr>
  <tr>
    <td>C35—C36—H36</td>
    <td>119.1</td>
  </tr>
  <tr>
    <td>C31—C36—H36</td>
    <td>119.1</td>
  </tr>
  <tr>
    <td>C34—O37—C38</td>
    <td>118.5 (5)</td>
  </tr>
  <tr>
    <td>O37—C38—H38A</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>O37—C38—H38B</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H38A—C38—H38B</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>O37—C38—H38C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H38A—C38—H38C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>H38B—C38—H38C</td>
    <td>109.5</td>
  </tr>
  <tr>
    <td>C42—C41—C46</td>
    <td>117.4 (5)</td>
  </tr>
  <tr>
    <td>C42—C41—C7</td>
    <td>121.1 (4)</td>
  </tr>
  <tr>
    <td>C46—C41—C7</td>
    <td>121.5 (5)</td>
  </tr>
  <tr>
    <td>C41—C42—C43</td>
    <td>122.6 (5)</td>
  </tr>
  <tr>
    <td>C41—C42—H42</td>
    <td>118.7</td>
  </tr>
  <tr>
    <td>C43—C42—H42</td>
    <td>118.7</td>
  </tr>
  <tr>
    <td>C42—C43—C44</td>
    <td>119.2 (6)</td>
  </tr>
  <tr>
    <td>C42—C43—H43</td>
    <td>120.4</td>
  </tr>
  <tr>
    <td>C44—C43—H43</td>
    <td>120.4</td>
  </tr>
  <tr>
    <td>O47—C44—C43</td>
    <td>125.1 (6)</td>
  </tr>
  <tr>
    <td>O47—C44—C45</td>
    <td>116.5 (5)</td>
  </tr>
  <tr>
    <td>C43—C44—C45</td>
    <td>118.4 (5)</td>
  </tr>
</table>
<table>
  <tbody>
    <tr>
      <td>C9—C10—C11</td>
      <td>107.9 (5)</td>
      <td>C46—C45—C44</td>
      <td>120.0 (5)</td>
    </tr>
    <tr>
      <td>C9—C10—H10</td>
      <td>126.1</td>
      <td>C46—C45—H45</td>
      <td>120.0</td>
    </tr>
    <tr>
      <td>C11—C10—H10</td>
      <td>126.1</td>
      <td>C44—C45—H45</td>
      <td>120.0</td>
    </tr>
    <tr>
      <td>N3—C11—C12</td>
      <td>126.6 (4)</td>
      <td>C45—C46—C41</td>
      <td>122.4 (6)</td>
    </tr>
    <tr>
      <td>N3—C11—C10</td>
      <td>108.9 (4)</td>
      <td>C45—C46—H46</td>
      <td>118.8</td>
    </tr>
    <tr>
      <td>C12—C11—C10</td>
      <td>124.5 (5)</td>
      <td>C41—C46—H46</td>
      <td>118.8</td>
    </tr>
    <tr>
      <td>C13—C12—C11</td>
      <td>124.2 (5)</td>
      <td>C44—O47—C48</td>
      <td>116.4 (6)</td>
    </tr>
    <tr>
      <td>C13—C12—C31</td>
      <td>118.1 (5)</td>
      <td>O47—C48—H48A</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>C11—C12—C31</td>
      <td>117.8 (5)</td>
      <td>O47—C48—H48B</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>N4—C13—C12</td>
      <td>126.0 (5)</td>
      <td>H48A—C48—H48B</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>N4—C13—C14</td>
      <td>109.8 (4)</td>
      <td>O47—C48—H48C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>C12—C13—C14</td>
      <td>124.2 (5)</td>
      <td>H48A—C48—H48C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>C15—C14—C13</td>
      <td>106.8 (4)</td>
      <td>H48B—C48—H48C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>C15—C14—H14</td>
      <td>126.6</td>
      <td>C53—C54—C55</td>
      <td>118.7 (5)</td>
    </tr>
    <tr>
      <td>C13—C14—H14</td>
      <td>126.6</td>
      <td>C53—C54—C57</td>
      <td>120.1 (5)</td>
    </tr>
    <tr>
      <td>C14—C15—C16</td>
      <td>107.4 (5)</td>
      <td>C55—C54—C57</td>
      <td>121.0 (5)</td>
    </tr>
    <tr>
      <td>C14—C15—H15</td>
      <td>126.3</td>
      <td>C56—C55—C54</td>
      <td>121.2 (5)</td>
    </tr>
    <tr>
      <td>C16—C15—H15</td>
      <td>126.3</td>
      <td>C56—C55—H55</td>
      <td>119.4</td>
    </tr>
    <tr>
      <td>N4—C16—C17</td>
      <td>126.6 (4)</td>
      <td>C54—C55—H55</td>
      <td>119.4</td>
    </tr>
    <tr>
      <td>N4—C16—C15</td>
      <td>109.2 (4)</td>
      <td>C55—C56—C51</td>
      <td>120.5 (5)</td>
    </tr>
    <tr>
      <td>C17—C16—C15</td>
      <td>124.2 (4)</td>
      <td>C55—C56—H56</td>
      <td>119.7</td>
    </tr>
    <tr>
      <td>C18—C17—C16</td>
      <td>124.4 (4)</td>
      <td>C51—C56—H56</td>
      <td>119.7</td>
    </tr>
    <tr>
      <td>C18—C17—C51</td>
      <td>118.7 (4)</td>
      <td>C52—C51—C56</td>
      <td>118.2 (5)</td>
    </tr>
    <tr>
      <td>C16—C17—C51</td>
      <td>117.0 (4)</td>
      <td>C52—C51—C17</td>
      <td>121.3 (4)</td>
    </tr>
    <tr>
      <td>N1—C18—C17</td>
      <td>126.4 (4)</td>
      <td>C56—C51—C17</td>
      <td>120.5 (5)</td>
    </tr>
    <tr>
      <td>N1—C18—C19</td>
      <td>109.2 (4)</td>
      <td>C51—C52—C53</td>
      <td>121.1 (5)</td>
    </tr>
    <tr>
      <td>C17—C18—C19</td>
      <td>124.4 (5)</td>
      <td>C51—C52—H52</td>
      <td>119.4</td>
    </tr>
    <tr>
      <td>C20—C19—C18</td>
      <td>106.8 (5)</td>
      <td>C53—C52—H52</td>
      <td>119.4</td>
    </tr>
    <tr>
      <td>C20—C19—H19</td>
      <td>126.6</td>
      <td>C54—C53—C52</td>
      <td>120.3 (5)</td>
    </tr>
    <tr>
      <td>C18—C19—H19</td>
      <td>126.6</td>
      <td>C54—C53—H53</td>
      <td>119.9</td>
    </tr>
    <tr>
      <td>C19—C20—C1</td>
      <td>107.0 (5)</td>
      <td>C52—C53—H53</td>
      <td>119.9</td>
    </tr>
    <tr>
      <td>C19—C20—H20</td>
      <td>126.5</td>
      <td>C59—O58—C57</td>
      <td>115.6 (4)</td>
    </tr>
    <tr>
      <td>C1—C20—H20</td>
      <td>126.5</td>
      <td>O60—C59—O58</td>
      <td>122.0 (5)</td>
    </tr>
    <tr>
      <td>C26—C21—C22</td>
      <td>117.1 (5)</td>
      <td>O60—C59—C61</td>
      <td>123.0 (5)</td>
    </tr>
    <tr>
      <td>C26—C21—C2</td>
      <td>121.6 (5)</td>
      <td>O58—C59—C61</td>
      <td>114.9 (5)</td>
    </tr>
    <tr>
      <td>C22—C21—C2</td>
      <td>121.3 (5)</td>
      <td>O58—C57—C54</td>
      <td>110.5 (4)</td>
    </tr>
    <tr>
      <td>C23—C22—C21</td>
      <td>120.9 (6)</td>
      <td>O58—C57—H57A</td>
      <td>109.6</td>
    </tr>
    <tr>
      <td>C23—C22—H22</td>
      <td>119.5</td>
      <td>C54—C57—H57A</td>
      <td>109.6</td>
    </tr>
    <tr>
      <td>C21—C22—H22</td>
      <td>119.5</td>
      <td>O58—C57—H57B</td>
      <td>109.6</td>
    </tr>
    <tr>
      <td>C24—C23—C22</td>
      <td>121.2 (6)</td>
      <td>C54—C57—H57B</td>
      <td>109.6</td>
    </tr>
    <tr>
      <td>C24—C23—H23</td>
      <td>119.4</td>
      <td>H57A—C57—H57B</td>
      <td>108.1</td>
    </tr>
    <tr>
      <td>C22—C23—H23</td>
      <td>119.4</td>
      <td>C59—O60—Zn1<sup>ii</sup></td>
      <td>139.3 (4)</td>
    </tr>
    <tr>
      <td>O27—C24—C23</td>
      <td>116.5 (6)</td>
      <td>N62—C61—C59</td>
      <td>120.3 (6)</td>
    </tr>
    <tr>
      <td>O27—C24—C25</td>
      <td>125.7 (6)</td>
      <td>N62—C61—H61</td>
      <td>119.9</td>
    </tr>
    <tr>
      <td>C23—C24—C25</td>
      <td>117.8 (5)</td>
      <td>C59—C61—H61</td>
      <td>119.9</td>
    </tr>
    <tr>
      <td>C26—C25—C24</td>
      <td>119.4 (6)</td>
      <td>N63—N62—C61</td>
      <td>176.5 (11)</td>
    </tr>
    <tr>
      <td>C18—N1—C1—C2</td>
      <td>178.4 (5)</td>
      <td>C51—C17—C18—C19</td>
      <td>-3.6 (7)</td>
    </tr>
  </tbody>
</table>
<table>
  <tr>
    <td>Zn1—N1—C1—C2</td>
    <td>-9.3 (7)</td>
  </tr>
  <tr>
    <td>C18—N1—C1—C20</td>
    <td>0.7 (6)</td>
  </tr>
  <tr>
    <td>Zn1—N1—C1—C20</td>
    <td>173.0 (4)</td>
  </tr>
  <tr>
    <td>N1—C1—C2—C3</td>
    <td>0.9 (8)</td>
  </tr>
  <tr>
    <td>C20—C1—C2—C3</td>
    <td>178.3 (5)</td>
  </tr>
  <tr>
    <td>N1—C1—C2—C21</td>
    <td>-177.4 (5)</td>
  </tr>
  <tr>
    <td>C20—C1—C2—C21</td>
    <td>0.0 (8)</td>
  </tr>
  <tr>
    <td>C1—C2—C3—N2</td>
    <td>-0.6 (9)</td>
  </tr>
  <tr>
    <td>C21—C2—C3—N2</td>
    <td>177.7 (5)</td>
  </tr>
  <tr>
    <td>C1—C2—C3—C4</td>
    <td>-179.2 (5)</td>
  </tr>
  <tr>
    <td>C21—C2—C3—C4</td>
    <td>-0.9 (8)</td>
  </tr>
  <tr>
    <td>C6—N2—C3—C2</td>
    <td>179.9 (5)</td>
  </tr>
  <tr>
    <td>Zn1—N2—C3—C2</td>
    <td>8.7 (8)</td>
  </tr>
  <tr>
    <td>C6—N2—C3—C4</td>
    <td>-1.2 (6)</td>
  </tr>
  <tr>
    <td>Zn1—N2—C3—C4</td>
    <td>-172.5 (3)</td>
  </tr>
  <tr>
    <td>C2—C3—C4—C5</td>
    <td>179.5 (5)</td>
  </tr>
  <tr>
    <td>N2—C3—C4—C5</td>
    <td>0.6 (6)</td>
  </tr>
  <tr>
    <td>C3—C4—C5—C6</td>
    <td>0.2 (6)</td>
  </tr>
  <tr>
    <td>C3—N2—C6—C7</td>
    <td>-178.5 (5)</td>
  </tr>
  <tr>
    <td>Zn1—N2—C6—C7</td>
    <td>-7.5 (7)</td>
  </tr>
  <tr>
    <td>C3—N2—C6—C5</td>
    <td>1.4 (6)</td>
  </tr>
  <tr>
    <td>Zn1—N2—C6—C5</td>
    <td>172.4 (3)</td>
  </tr>
  <tr>
    <td>C4—C5—C6—N2</td>
    <td>-1.0 (6)</td>
  </tr>
  <tr>
    <td>C4—C5—C6—C7</td>
    <td>178.9 (5)</td>
  </tr>
  <tr>
    <td>N2—C6—C7—C8</td>
    <td>-1.3 (8)</td>
  </tr>
  <tr>
    <td>C5—C6—C7—C8</td>
    <td>178.8 (5)</td>
  </tr>
  <tr>
    <td>N2—C6—C7—C41</td>
    <td>176.3 (5)</td>
  </tr>
  <tr>
    <td>C5—C6—C7—C41</td>
    <td>-3.6 (7)</td>
  </tr>
  <tr>
    <td>C11—N3—C8—C7</td>
    <td>179.2 (5)</td>
  </tr>
  <tr>
    <td>Zn1—N3—C8—C7</td>
    <td>6.9 (8)</td>
  </tr>
  <tr>
    <td>C11—N3—C8—C9</td>
    <td>0.3 (6)</td>
  </tr>
  <tr>
    <td>Zn1—N3—C8—C9</td>
    <td>-171.9 (4)</td>
  </tr>
  <tr>
    <td>C6—C7—C8—N3</td>
    <td>1.5 (8)</td>
  </tr>
  <tr>
    <td>C41—C7—C8—N3</td>
    <td>-176.1 (5)</td>
  </tr>
  <tr>
    <td>C6—C7—C8—C9</td>
    <td>-179.8 (5)</td>
  </tr>
  <tr>
    <td>C41—C7—C8—C9</td>
    <td>2.6 (8)</td>
  </tr>
  <tr>
    <td>N3—C8—C9—C10</td>
    <td>-0.6 (7)</td>
  </tr>
  <tr>
    <td>C7—C8—C9—C10</td>
    <td>-179.5 (5)</td>
  </tr>
  <tr>
    <td>C8—C9—C10—C11</td>
    <td>0.6 (7)</td>
  </tr>
  <tr>
    <td>C8—N3—C11—C12</td>
    <td>-178.4 (5)</td>
  </tr>
  <tr>
    <td>Zn1—N3—C11—C12</td>
    <td>-6.3 (8)</td>
  </tr>
  <tr>
    <td>C8—N3—C11—C10</td>
    <td>0.1 (6)</td>
  </tr>
  <tr>
    <td>Zn1—N3—C11—C10</td>
    <td>172.2 (4)</td>
  </tr>
  <tr>
    <td>C9—C10—C11—N3</td>
    <td>-0.5 (7)</td>
  </tr>
  <tr>
    <td>C9—C10—C11—C12</td>
    <td>178.0 (5)</td>
  </tr>
  <tr>
    <td>N3—C11—C12—C13</td>
    <td>-1.9 (9)</td>
  </tr>
  <tr>
    <td>C10—C11—C12—C13</td>
    <td>179.9 (5)</td>
  </tr>
  <tr>
    <td>N3—C11—C12—C31</td>
    <td>179.4 (5)</td>
  </tr>
</table>

<table>
  <tr>
    <td>N1—C18—C19—C20</td>
    <td>-1.7 (6)</td>
  </tr>
  <tr>
    <td>C17—C18—C19—C20</td>
    <td>-179.4 (5)</td>
  </tr>
  <tr>
    <td>C18—C19—C20—C1</td>
    <td>2.0 (6)</td>
  </tr>
  <tr>
    <td>N1—C1—C20—C19</td>
    <td>-1.8 (6)</td>
  </tr>
  <tr>
    <td>C2—C1—C20—C19</td>
    <td>-179.5 (5)</td>
  </tr>
  <tr>
    <td>C3—C2—C21—C26</td>
    <td>-77.8 (7)</td>
  </tr>
  <tr>
    <td>C1—C2—C21—C26</td>
    <td>100.6 (6)</td>
  </tr>
  <tr>
    <td>C3—C2—C21—C22</td>
    <td>102.3 (7)</td>
  </tr>
  <tr>
    <td>C1—C2—C21—C22</td>
    <td>-79.3 (8)</td>
  </tr>
  <tr>
    <td>C26—C21—C22—C23</td>
    <td>-0.1 (12)</td>
  </tr>
  <tr>
    <td>C2—C21—C22—C23</td>
    <td>179.9 (7)</td>
  </tr>
  <tr>
    <td>C21—C22—C23—C24</td>
    <td>4.0 (14)</td>
  </tr>
  <tr>
    <td>C22—C23—C24—O27</td>
    <td>174.6 (8)</td>
  </tr>
  <tr>
    <td>C22—C23—C24—C25</td>
    <td>-4.5 (12)</td>
  </tr>
  <tr>
    <td>O27—C24—C25—C26</td>
    <td>-177.7 (6)</td>
  </tr>
  <tr>
    <td>C23—C24—C25—C26</td>
    <td>1.3 (10)</td>
  </tr>
  <tr>
    <td>C22—C21—C26—C25</td>
    <td>-3.2 (10)</td>
  </tr>
  <tr>
    <td>C2—C21—C26—C25</td>
    <td>176.9 (6)</td>
  </tr>
  <tr>
    <td>C24—C25—C26—C21</td>
    <td>2.6 (10)</td>
  </tr>
  <tr>
    <td>C23—C24—O27—C28</td>
    <td>-172.0 (7)</td>
  </tr>
  <tr>
    <td>C25—C24—O27—C28</td>
    <td>7.0 (10)</td>
  </tr>
  <tr>
    <td>C13—C12—C31—C32</td>
    <td>-114.4 (6)</td>
  </tr>
  <tr>
    <td>C11—C12—C31—C32</td>
    <td>64.5 (7)</td>
  </tr>
  <tr>
    <td>C13—C12—C31—C36</td>
    <td>63.4 (7)</td>
  </tr>
  <tr>
    <td>C11—C12—C31—C36</td>
    <td>-117.7 (6)</td>
  </tr>
  <tr>
    <td>C36—C31—C32—C33</td>
    <td>-0.2 (8)</td>
  </tr>
  <tr>
    <td>C12—C31—C32—C33</td>
    <td>177.7 (5)</td>
  </tr>
  <tr>
    <td>C31—C32—C33—C34</td>
    <td>-0.9 (10)</td>
  </tr>
  <tr>
    <td>C32—C33—C34—O37</td>
    <td>-177.5 (6)</td>
  </tr>
  <tr>
    <td>C32—C33—C34—C35</td>
    <td>2.2 (10)</td>
  </tr>
  <tr>
    <td>C33—C34—C35—C36</td>
    <td>-2.3 (9)</td>
  </tr>
  <tr>
    <td>O37—C34—C35—C36</td>
    <td>177.4 (6)</td>
  </tr>
  <tr>
    <td>C34—C35—C36—C31</td>
    <td>1.2 (9)</td>
  </tr>
  <tr>
    <td>C32—C31—C36—C35</td>
    <td>0.1 (8)</td>
  </tr>
  <tr>
    <td>C12—C31—C36—C35</td>
    <td>-177.9 (5)</td>
  </tr>
  <tr>
    <td>C33—C34—O37—C38</td>
    <td>-177.4 (6)</td>
  </tr>
  <tr>
    <td>C35—C34—O37—C38</td>
    <td>2.9 (9)</td>
  </tr>
  <tr>
    <td>C8—C7—C41—C42</td>
    <td>81.1 (7)</td>
  </tr>
  <tr>
    <td>C6—C7—C41—C42</td>
    <td>-96.7 (6)</td>
  </tr>
  <tr>
    <td>C8—C7—C41—C46</td>
    <td>-95.9 (6)</td>
  </tr>
  <tr>
    <td>C6—C7—C41—C46</td>
    <td>86.3 (7)</td>
  </tr>
  <tr>
    <td>C46—C41—C42—C43</td>
    <td>-1.5 (9)</td>
  </tr>
  <tr>
    <td>C7—C41—C42—C43</td>
    <td>-178.6 (6)</td>
  </tr>
  <tr>
    <td>C41—C42—C43—C44</td>
    <td>2.8 (11)</td>
  </tr>
  <tr>
    <td>C42—C43—C44—O47</td>
    <td>-179.2 (6)</td>
  </tr>
  <tr>
    <td>C42—C43—C44—C45</td>
    <td>-1.5 (10)</td>
  </tr>
  <tr>
    <td>O47—C44—C45—C46</td>
    <td>176.9 (7)</td>
  </tr>
  <tr>
    <td>C43—C44—C45—C46</td>
    <td>-1.0 (10)</td>
  </tr>
</table>
<table><tr><td>C10—C11—C12—C31</td><td>1.1 (8)</td></tr><tr><td>C16—N4—C13—C12</td><td>-179.4 (5)</td></tr><tr><td>Zn1—N4—C13—C12</td><td>6.5 (8)</td></tr><tr><td>C16—N4—C13—C14</td><td>-1.2 (6)</td></tr><tr><td>Zn1—N4—C13—C14</td><td>-175.3 (4)</td></tr><tr><td>C11—C12—C13—N4</td><td>1.8 (8)</td></tr><tr><td>C31—C12—C13—N4</td><td>-179.5 (5)</td></tr><tr><td>C11—C12—C13—C14</td><td>-176.1 (5)</td></tr><tr><td>C31—C12—C13—C14</td><td>2.6 (8)</td></tr><tr><td>N4—C13—C14—C15</td><td>1.3 (7)</td></tr><tr><td>C12—C13—C14—C15</td><td>179.5 (5)</td></tr><tr><td>C13—C14—C15—C16</td><td>-0.9 (6)</td></tr><tr><td>C13—N4—C16—C17</td><td>178.1 (5)</td></tr><tr><td>Zn1—N4—C16—C17</td><td>-7.6 (8)</td></tr><tr><td>C13—N4—C16—C15</td><td>0.7 (6)</td></tr><tr><td>Zn1—N4—C16—C15</td><td>174.9 (4)</td></tr><tr><td>C14—C15—C16—N4</td><td>0.2 (6)</td></tr><tr><td>C14—C15—C16—C17</td><td>-177.4 (5)</td></tr><tr><td>N4—C16—C17—C18</td><td>1.4 (8)</td></tr><tr><td>C15—C16—C17—C18</td><td>178.5 (5)</td></tr><tr><td>N4—C16—C17—C51</td><td>-178.1 (5)</td></tr><tr><td>C15—C16—C17—C51</td><td>-1.0 (7)</td></tr><tr><td>C1—N1—C18—C17</td><td>178.2 (5)</td></tr><tr><td>Zn1—N1—C18—C17</td><td>6.0 (7)</td></tr><tr><td>C1—N1—C18—C19</td><td>0.5 (6)</td></tr><tr><td>Zn1—N1—C18—C19</td><td>-171.7 (3)</td></tr><tr><td>C16—C17—C18—N1</td><td>-0.4 (8)</td></tr><tr><td>C51—C17—C18—N1</td><td>179.1 (5)</td></tr><tr><td>C16—C17—C18—C19</td><td>176.9 (5)</td></tr></table>

<table><tr><td>C44—C45—C46—C41</td><td>2.4 (11)</td></tr><tr><td>C42—C41—C46—C45</td><td>-1.2 (10)</td></tr><tr><td>C7—C41—C46—C45</td><td>175.9 (6)</td></tr><tr><td>C43—C44—O47—C48</td><td>-0.2 (12)</td></tr><tr><td>C45—C44—O47—C48</td><td>-177.9 (9)</td></tr><tr><td>C53—C54—C55—C56</td><td>2.2 (9)</td></tr><tr><td>C57—C54—C55—C56</td><td>177.2 (5)</td></tr><tr><td>C54—C55—C56—C51</td><td>-1.0 (9)</td></tr><tr><td>C55—C56—C51—C52</td><td>-0.8 (9)</td></tr><tr><td>C55—C56—C51—C17</td><td>178.2 (5)</td></tr><tr><td>C18—C17—C51—C52</td><td>-71.5 (6)</td></tr><tr><td>C16—C17—C51—C52</td><td>108.0 (6)</td></tr><tr><td>C18—C17—C51—C56</td><td>109.5 (6)</td></tr><tr><td>C16—C17—C51—C56</td><td>-71.0 (7)</td></tr><tr><td>C56—C51—C52—C53</td><td>1.5 (8)</td></tr><tr><td>C17—C51—C52—C53</td><td>-177.6 (5)</td></tr><tr><td>C55—C54—C53—C52</td><td>-1.5 (8)</td></tr><tr><td>C57—C54—C53—C52</td><td>-176.6 (5)</td></tr><tr><td>C51—C52—C53—C54</td><td>-0.3 (8)</td></tr><tr><td>C57—O58—C59—O60</td><td>-2.9 (7)</td></tr><tr><td>C57—O58—C59—C61</td><td>180.0 (5)</td></tr><tr><td>C59—O58—C57—C54</td><td>86.2 (5)</td></tr><tr><td>C53—C54—C57—O58</td><td>-108.5 (5)</td></tr><tr><td>C55—C54—C57—O58</td><td>76.6 (6)</td></tr><tr><td>O58—C59—O60—Zn1<sup>ii</sup></td><td>174.5 (4)</td></tr><tr><td>C61—C59—O60—Zn1<sup>ii</sup></td><td>-8.5 (9)</td></tr><tr><td>O60—C59—C61—N62</td><td>-174.9 (7)</td></tr><tr><td>O58—C59—C61—N62</td><td>2.2 (10)</td></tr></table>

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