Crystal structure of
4-(3,5-dimethyl-1,7-diphenyl-1,7-dihydrodipyrazolo[3,4-
b:4',3'- e ]pyridin-4-yl)phenol dimethyl sulfoxide
disolvate

N'Gandi N'Gaza, Erwann Jeanneau, Catherine Marestin, Regis Mercier

► To cite this version:

N'Gandi N'Gaza, Erwann Jeanneau, Catherine Marestin, Regis Mercier. Crystal structure of 4-(3,5-dimethyl-1,7-diphenyl-1,7-dihydrodipyrazolo[3,4- b:4',3'- e ]pyridin-4-yl)phenol dimethyl sulfoxide disolvate. Acta crystallographica Section E: Crystallographic communications [2015-..], 2025, 81 (8), pp.711-713. 10.1107/S2056989025006152. hal-05403517

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Acta Cryst.

E

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN 2056-9890

Received 7 May 2025

Accepted 11 July 2025

Edited by D. R. Manke, University of Massachusetts Dartmouth, USA

**Keywords:** crystal structure;
dihydrodipyrazolopyridine.

CCDC reference: 2472025

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

# Crystal structure of 4-(3,5-dimethyl-1,7-diphenyl-1,7-dihydrodipyrazolo[3,4-b:4',3'-e]pyridin-4-yl)-phenol dimethyl sulfoxide disolvate

N'gandi N'gaza,ª Erwann Jeanneau,ᵇ* Catherine Marestinª and Regis Mercierª

A new bispyrazolylpyridine(BPP)-containing derivative, namely, 4-(3,5-dimethyl-1,7-diphenyl-1,7-dihydrodipyrazolo[3,4-b:4',3'-e]pyridin-4-yl)phenol (1), C27H21N5O·2C2H6OS, has been synthesized by a Hantzsch multicomponent reaction using acetic acid (AcOH) as solvent and copper(II) acetate monohydrate [Cu(OAc)2·H2O] as mild oxidant. The structure of the compound was fully characterized by single-crystal X-ray diffraction. The crystallographic study shows that the molecule crystallizes in the triclinic system with space group P\bar{1}, with one molecule per asymmetric unit. Whereas the phenolic substituent in the *para* position of the pyridine group is highly twisted from the planar bispyrazolopyridine core [56.19 (4)°], the two phenyl rings present on the nitrogen atoms are only slightly distorted [11.77 (5) and 29.17 (5)°]. The crystal structure is consolidated by intermolecular C—H···O hydrogen bonds and π–π stacking interactions.

## 1. Chemical context

Bis-pyrazolo[3,4-b:4',3'-e]pyridine (BPP) is a tricyclic scaffold known for its strong fluorescence, making its derivatives valuable as light-emitting materials in electroluminescent devices (Safaei-Ghomi *et al.*, 2016; Ko & Tao, 2001). BPP-containing derivatives are usually synthesized by pseudo three-component reaction between 5-aminopyrazole and aromatic aldehydes at 493–523 K. Such experimental conditions result in low to moderate yields (Gondek *et al.*, 2012; Puchala *et al.*, 1997). Alternative methods include microwave-assisted, solvent-free conditions (Quiroga *et al.*, 2005), ionic liquid-mediated synthesis (Shi & Yang, 2008), and FeCl3 catalysis in DMSO at 403 K (Qiu *et al.*, 2018).

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As part of our ongoing work related to the synthesis of nitrogen-containing heterocycles, we synthesized the title compound **1** via oxidative multicomponent condensation using acetic acid (AcOH) as a solvent and copper(II) acetate

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Published under a CC BY 4.0 licence

<footnote>ªUniversite Claude Bernard Lyon1, Université Jean Monnet, CNRS UMR 5223, Ingénierie des Matériaux Polymères, F69 621 Cédex, France, and ᵇCentre de Diffractométrie Henrin Longchambon, Universite Claude Bernard Lyon1, 69100 Villeurbanne, France. *Correspondence e-mail: erwann.jeanneau@univ-lyon1.fr</footnote>
<figure><img src="image_7.png" /><figcaption>**Figure 1**</figcaption></figure>

Molecular view of the title compound with displacement ellipsoids drawn at the 30% probability level (DMSO solvent molecules are omitted for clarity).

monohydrate [Cu(OAc)₂·H₂O] as a mild oxidant for dihydropyridine derivatives (Bell & Rothenberger, 1987; Qiu *et al.*, 2018). In such conditions, analytically pure phenol-containing bispyrazolopyridine was isolated with 70% yield.

## 2. Structural commentary

The asymmetric unit of the title compound is composed of a 4-(3,5-dimethyl-1,7-diphenyl-1,7-dihydrodipyrazolo[3,4-b'4',3'-e]pyridin-4-yl)phenol molecule and two crystallographically distinct DMSO molecules. The twelve-membered fused-ring system is essentially planar and symmetrical about the N3···C7 line (Fig. 1). The r.m.s. deviation of the twelve atoms from the mean plane is 0.035 Å. The dihedral angles between the phenyl rings and the mean plane of the twelve-membered fused-ring system are 11.77 (5) and 29.17 (5)° for the ring defined by atoms C22–C27 and the ring defined by atoms C16–C21, respectively. The dihedral angle between the twelve-

<figure><img src="image_8.png" /><figcaption>**Figure 2**</figcaption></figure>

View of the packing of the title compound with intermolecular interactions represented as dotted lines (black and blue: –π stacking, red: C–H···O hydrogen bonding.

<caption>**Table 1**</caption>

Hydrogen-bond geometry (Å, °).

<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>C19–H19···O1<sup>i</sup></td><td>0.95</td><td>2.37</td><td>3.283 (2)</td><td>160</td></tr><tr><td>C29–H29B···O2<sup>ii</sup></td><td>0.98</td><td>2.48</td><td>3.312 (3)</td><td>142</td></tr></tbody></table>

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

membered ring and the phenolic substituent is much greater with a value of 56.19 (4)°, due to the steric hindrance of the two methyl groups. This BPP derivative co-crystallizes with two DMSO molecules, one of which exhibits a slight positional disorder of the sulfur atoms over two crystallographic positions with occupancies of 0.923 (2) and 0.077 (2).

## 3. Supramolecular features

The BPP-derivative molecules lie nearly perpendicular to the *a* axis of the unit cell and are related to one another through an inversion center. This leads to chains where the molecules are arranged in a head-to-tail manner with two distinct interplanar distances (Fig. 2). The distance of 3.9478 (9) Å corresponds to π–π interactions between two adjacent pyridine rings whereas the shorter distance of 3.6529 (9) Å is probably due to a combination of the pyridine rings π–π interaction reinforced by an interaction between the hydrogen atoms from the phenyl groups and the pyrazole rings. These infinite chains are linked together along the *c*-axis direction by C–H···O hydrogen-bonding interactions (Table 1).

## 4. Database survey

A structural fragment search for the twelve-membered fused-ring substituted with two phenyl rings in the Cambridge Structural Database (CSD version 5.46, last update November 2024; Groom *et al.*, 2016) resulted in five hits. One hit corresponds to the structure of the unsubstituted fragment (ADAJAR; Portilla *et al.*, 2006) and the others correspond to the similar fused-ring system with different substituents: a phenyl ring (FEPDEJ; Krygowski *et al.*, 1998; FEPDEJ01; Low *et al.*, 2003b), phenylNMe2 (FEPDUZ; Krygowski *et al.*, 1998), a pyridin (IKIFEN; Low *et al.*, 2003a and a COPh (KEQRAC; Gao *et al.*, 2018). While the two phenyl rings in the unsubstituted compound (ADAJAR) both have a dihedral angle of 27.9 (3)° with respect to the BPP core, the title compound displays one small angle of 11.77 (5)° and a larger one of 29.17 (5)°. This feature is also found for most of the substituted referenced compounds [FEPDEJ01: 5.00 (3) and 26.49 (3)°; FEDPUZ: 8.23 (6)° and 34.65 (6)°; IKIFEN: 7.11 (3) and 22.8 (3)°] with the exception of KEQRAC where the phenyl rings both make a small dihedral angle with respect to the BPP core [7.38 (8) and 8.12 (6)°]. Similarly, the angles between the BPP core and the substituent located opposite the phenyl rings lie in a range of about 10° [FEPDEJ01: 62.92 (3); FEDPUZ: 67.94 (5)°; IKIFEN: 70.46 (3)°]. The title compound lies in the bottom range with a dihedral angle of 56.19 (4)° while KEQRAC displays an almost right angle [ie., 89.19 (5)°] between its substituent and the BPP core.
## 5. Synthesis and crystallization

A 50 mL single-neck round-bottom flask equipped with a magnetic stirring bar and a condenser was charged with 3-methyl-1-phenyl-1H-pyrazol-5-amine (11.5 mmol, 2 eq), benzaldehyde (5.7 mmol, 1 eq), and Cu(OAc)₂·H₂O (2.8 mmol, 0.5 eq) in 20 mL of AcOH. Triethylamine (1 mL) was added, and the reaction mixture was heated at 403 K for 48 h under continuous stirring. Reaction progress was monitored by thin-layer chromatography (TLC) (DCM/Petroleum ether, 70:30 v/v). Upon completion, the reaction mixture was precipitated in 200 mL of demineralized water, and the crude solid was collected by filtration. The solid was dissolved in 1,3-dioxolane. The resulting mixture was charcoal-washed, filtered through a Celite pad, and the solvent was evaporated. The product was purified via column chromatography (DCM/petroleum ether, 3:1 v/v), yielding a pure white solid. 70% yield [m.p. 558 K; lit. 430–431 K (Hennig et al., 1990), 500–501, (Shi et al., 2008)]. Recrystallization from dimethyl sulfoxide (DMSO) gave single crystals suitable for X-ray diffraction analysis.

## 6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. One of the two DMSO solvent molecules was slightly disordered over two positions. SADI restraints were used for this molecule in the course of the refinement. H atoms were positioned geometrically and refined as riding [C–H = 0.5–0.98 Å, Uiso(H) = 1.2–1.5Ueq(C)].

## References

* Bell, T. W. & Rothenberger, S. D. (1987). *Tetrahedron Lett.* **28**, 4817–4820.

* Brandenburg, K. & Putz, H. (2025). *DIAMOND*. Crystal Impact GbR, Bonn, Germany.

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

* Gao, Q., He, S., Wu, X., Zhang, J., Bai, S., Wu, Y. & Wu, A. (2018). *Org. Chem. Front.* **5**, 765–768.

* Gondek, E., Nizioł, J., Danel, A., Jarosz, B., Gąsiorski, P. & Kityk, A. V. (2012). *Spectrochim. Acta A Mol. Biomol. Spectrosc.* **95**, 610–613.

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

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* Ko, C. W. & Tao, Y. T. (2001). *Appl. Phys. Lett.* **79**, 4234–4236.

* Krygowski, T. M., Anulewicz, R., Cyrański, M. K., Puchala, A. & Rasala, D. (1998). *Tetrahedron* **54**, 12295–12300.

<caption>**Table 2**</caption>

Experimental details.

<table><tr><td>Crystal data</td><td></td></tr><tr><td>Chemical formula</td><td>C<sub>27</sub>H<sub>21</sub>N<sub>5</sub>O·2C<sub>2</sub>H<sub>6</sub>OS</td></tr><tr><td>M<sub>r</sub></td><td>587.74</td></tr><tr><td>Crystal system, space group</td><td>Triclinic, <i>P</i>1</td></tr><tr><td>Temperature (K)</td><td>100</td></tr><tr><td><i>a</i>, <i>b</i>, <i>c</i> (Å)</td><td>7.5736 (1), 12.0242 (1), 16.1594 (2)</td></tr><tr><td>α, β<sub>z</sub> γ (°)</td><td>91.824 (1), 100.953 (1), 92.657 (1)</td></tr><tr><td><i>V</i> (Å<sup>3</sup>)</td><td>1441.98 (3)</td></tr><tr><td><i>Z</i></td><td>2</td></tr><tr><td>Radiation type</td><td>Cu Kα</td></tr><tr><td>μ (mm<sup>-1</sup>)</td><td>2.02</td></tr><tr><td>Crystal size (mm)</td><td>0.40 × 0.09 × 0.04</td></tr><tr><td>Data collection</td><td></td></tr><tr><td>Diffractometer</td><td>XtaLAB Synergy, Dualflex, HyPix-Arc 100</td></tr><tr><td>Absorption correction</td><td>Multi-scan (CrysAlis PRO; Rigaku OD, 2022)</td></tr><tr><td><i>T</i><sub>min</sub>, <i>T</i><sub>max</sub></td><td>0.503, 1.000</td></tr><tr><td>No. of measured, independent and observed [<i>I</i> > 2σ(<i>I</i>)] reflections</td><td>53004, 5873, 5331</td></tr><tr><td><i>R</i><sub>int</sub></td><td>0.051</td></tr><tr><td>(sin θ/λ)<sub>max</sub> (Å<sup>-1</sup>)</td><td>0.634</td></tr><tr><td>Refinement</td><td></td></tr><tr><td><i>R</i>[<i>F</i><sup>2</sup> > 2σ(<i>F</i><sup>2</sup>)], <i>wR</i>(<i>F</i><sup>2</sup>), <i>S</i></td><td>0.059, 0.171, 1.06</td></tr><tr><td>No. of reflections</td><td>5873</td></tr><tr><td>No. of parameters</td><td>387</td></tr><tr><td>No. of restraints</td><td>7</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>0.83, -0.52</td></tr></table>

Computer programs: *CrysAlis PRO* (Rigaku OD, 2022), *SHELXT2018/2* (Sheldrick, 2015a), *SHELXL2018/3* (Sheldrick, 2015b), *OLEX2* (Dolomanov et al., 2009), and *DIAMOND* (Brandenburg & Putz, 2025).

* Low, J. N., Cobo, J., Portilla, J. & Quiroga, J. (2003a). *Acta Cryst.* **E59**, o1327–o1329.

* Low, J. N., Cobo, J., Portilla, J. & Quiroga, J. (2003b). *Acta Cryst.* **E59**, o1330–o1331.

* Portilla, J., de la Torre, J. M., Cobo, J., Low, J. N. & Glidewell, C. (2006). *Acta Cryst.* **E62**, o1676–o1678.

* Puchala, A., Rasala, D., Kolehmainen, E. & Prokesová, M. (1997). *Org. Prep. Proced. Int.* **29**, 226–230.

* Qiu, R., Qiao, S., Peng, B., Long, J. & Yin, G. (2018). *Tetrahedron Lett.* **59**, 3884–3888.

* Quiroga, J., Portilla, J., Insuasty, B., Abonía, R., Nogueras, M., Sortino, M. & Zacchino, S. (2005). *J. Heterocycl. Chem.* **42**, 61–66.

* Rigaku OD (2022). *CrysAlis PRO*. Rigaku Corporation, Wroclaw, Poland.

* Safaei-Ghomi, J., Sadeghzadeh, R. & Shahbazi-Alavi, H. (2016). *RSC Adv.* **6**, 33676–33685.

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

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* Shi, D.-Q. & Yang, F. (2008). *J. Chin. Chem. Soc.* **55**, 755–760.
supporting information

Acta Cryst. (2025). E81, 711-713 [https://doi.org/10.1107/S2056989025006152]

# Crystal structure of 4-(3,5-dimethyl-1,7-diphenyl-1,7-dihydrodipyrazolo[3,4- b:4',3'-e]pyridin-4-yl)phenol dimethyl sulfoxide disolvate

N'gandi N'gaza, Erwann Jeanneau, Catherine Marestin and Regis Mercier

## Computing details

4-(3,5-Dimethyl-1,7-diphenyl-1,7-dihydrodipyrazolo[3,4- b:4',3'-e]pyridin-4-yl)phenol dimethyl sulfoxide disolvate

### Crystal data

C27H21N5O·2C2H6OS

$M_r = 587.74$

Triclinic, P1

$a = 7.5736 (1) Å$

$b = 12.0242 (1) Å$

$c = 16.1594 (2) Å$

$\alpha = 91.824 (1)°$

$\beta = 100.953 (1)°$

$\gamma = 92.657 (1)°$

$V = 1441.98 (3) Å³$

$Z = 2$

$F(000) = 620$

$D_x = 1.354 \text{ Mg m}^{-3}$

Cu Kα radiation, $\lambda = 1.54184$ Å

Cell parameters from 34222 reflections

$\theta = 5.6-77.6°$

$\mu = 2.02 \text{ mm}^{-1}$

$T = 100 \text{ K}$

Needle, colourless

$0.40 \times 0.09 \times 0.04 \text{ mm}$

### Data collection

XtaLAB Synergy, Dualflex, HyPix-Arc 100 diffractometer

Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source

Mirror monochromator

Detector resolution: 10.0000 pixels mm⁻¹

$\omega$ scans

Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2022)

$T_{\text{min}} = 0.503, T_{\text{max}} = 1.000$

53004 measured reflections

5873 independent reflections

5331 reflections with $I > 2\sigma(I)$

$R_{\text{int}} = 0.051$

$\theta_{\text{max}} = 77.9°, \theta_{\text{min}} = 5.6°$

$h = -9 \rightarrow 8$

$k = -14 \rightarrow 15$

$l = -19 \rightarrow 20$

### Refinement

Refinement on $F^2$

Least-squares matrix: full

$R[F^2 > 2\sigma(F^2)] = 0.059$

$wR(F^2) = 0.171$

$S = 1.06$

5873 reflections

387 parameters

7 restraints

Primary atom site location: dual

Hydrogen site location: inferred from
neighbouring sites

H-atom parameters constrained

$w = 1/[\sigma^2(F_o^2) + (0.1271P)^2 + 0.4936P]$ where $P = (F_o^2 + 2F_c^2)/3$

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

$\Delta\rho_{\text{max}} = 0.83 \text{ e Å}^{-3}$

$\Delta\rho_{\text{min}} = -0.52 \text{ e Å}^{-3}$
Special details

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

<table><caption>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)</caption><thead><tr><th></th><th>x</th><th>y</th><th>z</th><th>U<sub>iso</sub>*/U<sub>eq</sub></th><th>Occ. (&lt;1)</th></tr></thead><tbody><tr><td>S1</td><td>0.30701 (7)</td><td>0.22453 (4)</td><td>0.99930 (3)</td><td>0.03382 (17)</td><td></td></tr><tr><td>O3</td><td>0.3487 (2)</td><td>0.28941 (14)</td><td>0.92642 (9)</td><td>0.0404 (4)</td><td></td></tr><tr><td>C28</td><td>0.2308 (3)</td><td>0.3217 (2)</td><td>1.06824 (16)</td><td>0.0489 (6)</td><td></td></tr><tr><td>H28A</td><td>0.329852</td><td>0.375409</td><td>1.092503</td><td>0.073*</td><td></td></tr><tr><td>H28B</td><td>0.189338</td><td>0.282048</td><td>1.113635</td><td>0.073*</td><td></td></tr><tr><td>H28C</td><td>0.131123</td><td>0.361337</td><td>1.036545</td><td>0.073*</td><td></td></tr><tr><td>C29</td><td>0.0947 (3)</td><td>0.1519 (2)</td><td>0.96113 (14)</td><td>0.0436 (5)</td><td></td></tr><tr><td>H29A</td><td>0.005564</td><td>0.205230</td><td>0.938663</td><td>0.065*</td><td></td></tr><tr><td>H29B</td><td>0.055373</td><td>0.113158</td><td>1.007445</td><td>0.065*</td><td></td></tr><tr><td>H29C</td><td>0.106705</td><td>0.097539</td><td>0.916327</td><td>0.065*</td><td></td></tr><tr><td>S2B</td><td>0.3600 (11)</td><td>0.0684 (7)</td><td>0.1856 (4)</td><td>0.068 (3)</td><td>0.077 (2)</td></tr><tr><td>O2</td><td>0.1632 (2)</td><td>0.06089 (13)</td><td>0.15533 (10)</td><td>0.0392 (4)</td><td></td></tr><tr><td>C30</td><td>0.4071 (3)</td><td>0.0163 (2)</td><td>0.28850 (14)</td><td>0.0401 (5)</td><td></td></tr><tr><td>H30D</td><td>0.302046</td><td>-0.028140</td><td>0.298583</td><td>0.060*</td><td>0.077 (2)</td></tr><tr><td>H30E</td><td>0.434494</td><td>0.078689</td><td>0.330174</td><td>0.060*</td><td>0.077 (2)</td></tr><tr><td>H30F</td><td>0.510854</td><td>-0.030569</td><td>0.293577</td><td>0.060*</td><td>0.077 (2)</td></tr><tr><td>H30A</td><td>0.474427</td><td>0.085736</td><td>0.281302</td><td>0.060*</td><td>0.923 (2)</td></tr><tr><td>H30B</td><td>0.491644</td><td>-0.039993</td><td>0.310225</td><td>0.060*</td><td>0.923 (2)</td></tr><tr><td>H30C</td><td>0.327311</td><td>0.029805</td><td>0.328486</td><td>0.060*</td><td>0.923 (2)</td></tr><tr><td>C31</td><td>0.4576 (3)</td><td>-0.0358 (2)</td><td>0.13218 (16)</td><td>0.0459 (6)</td><td></td></tr><tr><td>H31D</td><td>0.370032</td><td>-0.098893</td><td>0.115536</td><td>0.069*</td><td>0.077 (2)</td></tr><tr><td>H31E</td><td>0.564391</td><td>-0.061065</td><td>0.169611</td><td>0.069*</td><td>0.077 (2)</td></tr><tr><td>H31F</td><td>0.492617</td><td>-0.005288</td><td>0.081776</td><td>0.069*</td><td>0.077 (2)</td></tr><tr><td>H31A</td><td>0.409674</td><td>-0.059790</td><td>0.073354</td><td>0.069*</td><td>0.923 (2)</td></tr><tr><td>H31B</td><td>0.545261</td><td>-0.088296</td><td>0.157723</td><td>0.069*</td><td>0.923 (2)</td></tr><tr><td>H31C</td><td>0.516730</td><td>0.038740</td><td>0.134179</td><td>0.069*</td><td>0.923 (2)</td></tr><tr><td>O1</td><td>0.6914 (2)</td><td>0.32737 (14)</td><td>0.91211 (9)</td><td>0.0390 (4)</td><td></td></tr><tr><td>H1</td><td>0.584381</td><td>0.310132</td><td>0.915665</td><td>0.059*</td><td></td></tr><tr><td>N1</td><td>0.69150 (19)</td><td>0.23346 (12)</td><td>0.41144 (9)</td><td>0.0221 (3)</td><td></td></tr><tr><td>N2</td><td>0.7253 (2)</td><td>0.33241 (12)</td><td>0.37466 (9)</td><td>0.0212 (3)</td><td></td></tr><tr><td>N3</td><td>0.78724 (19)</td><td>0.52537 (12)</td><td>0.41716 (9)</td><td>0.0200 (3)</td><td></td></tr><tr><td>N4</td><td>0.82744 (19)</td><td>0.70547 (12)</td><td>0.49050 (9)</td><td>0.0209 (3)</td><td></td></tr><tr><td>N5</td><td>0.8160 (2)</td><td>0.74841 (12)</td><td>0.56996 (9)</td><td>0.0228 (3)</td><td></td></tr><tr><td>C1</td><td>0.6986 (3)</td><td>0.35225 (16)</td><td>0.83146 (11)</td><td>0.0283 (4)</td><td></td></tr><tr><td>C2</td><td>0.5578 (2)</td><td>0.32194 (15)</td><td>0.76418 (11)</td><td>0.0255 (4)</td><td></td></tr><tr><td>H2</td><td>0.453109</td><td>0.281988</td><td>0.774056</td><td>0.031*</td><td></td></tr><tr><td>C3</td><td>0.5709 (2)</td><td>0.35011 (14)</td><td>0.68320 (11)</td><td>0.0218 (3)</td><td></td></tr><tr><td>H3</td><td>0.475339</td><td>0.328080</td><td>0.637669</td><td>0.026*</td><td></td></tr><tr><td>C4</td><td>0.7221 (2)</td><td>0.41044 (14)</td><td>0.66714 (11)</td><td>0.0207 (3)</td><td></td></tr></tbody></table>
<table><tr><td>C5</td><td>0.8633 (2)</td><td>0.43868 (15)</td><td>0.73544 (11)</td><td>0.0237 (4)</td></tr><tr><td>H5</td><td>0.967841</td><td>0.479059</td><td>0.725874</td><td>0.028*</td></tr><tr><td>C6</td><td>0.8530 (3)</td><td>0.40889 (16)</td><td>0.81619 (11)</td><td>0.0275 (4)</td></tr><tr><td>H6</td><td>0.951264</td><td>0.427000</td><td>0.861367</td><td>0.033*</td></tr><tr><td>C7</td><td>0.7347 (2)</td><td>0.44764 (14)</td><td>0.58206 (10)</td><td>0.0192 (3)</td></tr><tr><td>C8</td><td>0.7176 (2)</td><td>0.37525 (14)</td><td>0.51013 (10)</td><td>0.0194 (3)</td></tr><tr><td>C9</td><td>0.6869 (2)</td><td>0.25707 (14)</td><td>0.49090 (11)</td><td>0.0212 (3)</td></tr><tr><td>C10</td><td>0.6516 (2)</td><td>0.16418 (14)</td><td>0.54567 (11)</td><td>0.0243 (4)</td></tr><tr><td>H10A</td><td>0.530716</td><td>0.168890</td><td>0.558458</td><td>0.036*</td></tr><tr><td>H10B</td><td>0.741089</td><td>0.169984</td><td>0.598313</td><td>0.036*</td></tr><tr><td>H10C</td><td>0.659929</td><td>0.092663</td><td>0.516209</td><td>0.036*</td></tr><tr><td>C11</td><td>0.7439 (2)</td><td>0.42006 (14)</td><td>0.43258 (10)</td><td>0.0197 (3)</td></tr><tr><td>C12</td><td>0.7968 (2)</td><td>0.59164 (14)</td><td>0.48631 (10)</td><td>0.0193 (3)</td></tr><tr><td>C13</td><td>0.7707 (2)</td><td>0.56000 (14)</td><td>0.56730 (10)</td><td>0.0198 (3)</td></tr><tr><td>C14</td><td>0.7831 (2)</td><td>0.66405 (14)</td><td>0.61538 (11)</td><td>0.0219 (4)</td></tr><tr><td>C15</td><td>0.7561 (3)</td><td>0.68638 (15)</td><td>0.70355 (11)</td><td>0.0263 (4)</td></tr><tr><td>H15A</td><td>0.853542</td><td>0.655118</td><td>0.743345</td><td>0.039*</td></tr><tr><td>H15B</td><td>0.640259</td><td>0.651681</td><td>0.710256</td><td>0.039*</td></tr><tr><td>H15C</td><td>0.756755</td><td>0.766976</td><td>0.714839</td><td>0.039*</td></tr><tr><td>C16</td><td>0.7378 (2)</td><td>0.33181 (14)</td><td>0.28846 (11)</td><td>0.0215 (4)</td></tr><tr><td>C17</td><td>0.7958 (3)</td><td>0.23643 (15)</td><td>0.25179 (12)</td><td>0.0266 (4)</td></tr><tr><td>H17</td><td>0.826235</td><td>0.173435</td><td>0.284544</td><td>0.032*</td></tr><tr><td>C18</td><td>0.8083 (3)</td><td>0.23475 (17)</td><td>0.16735 (12)</td><td>0.0309 (4)</td></tr><tr><td>H18</td><td>0.846711</td><td>0.169958</td><td>0.142210</td><td>0.037*</td></tr><tr><td>C19</td><td>0.7653 (3)</td><td>0.32672 (18)</td><td>0.11898 (12)</td><td>0.0307 (4)</td></tr><tr><td>H19</td><td>0.775542</td><td>0.325209</td><td>0.061267</td><td>0.037*</td></tr><tr><td>C20</td><td>0.7073 (3)</td><td>0.42092 (17)</td><td>0.15576 (12)</td><td>0.0291 (4)</td></tr><tr><td>H20</td><td>0.677766</td><td>0.483941</td><td>0.122899</td><td>0.035*</td></tr><tr><td>C21</td><td>0.6921 (2)</td><td>0.42377 (15)</td><td>0.24026 (11)</td><td>0.0250 (4)</td></tr><tr><td>H21</td><td>0.650837</td><td>0.488008</td><td>0.264866</td><td>0.030*</td></tr><tr><td>C22</td><td>0.8558 (2)</td><td>0.78004 (14)</td><td>0.42752 (11)</td><td>0.0206 (3)</td></tr><tr><td>C23</td><td>0.8872 (2)</td><td>0.74094 (14)</td><td>0.35001 (11)</td><td>0.0239 (4)</td></tr><tr><td>H23</td><td>0.890289</td><td>0.663167</td><td>0.338480</td><td>0.029*</td></tr><tr><td>C24</td><td>0.9139 (3)</td><td>0.81630 (15)</td><td>0.28935 (12)</td><td>0.0266 (4)</td></tr><tr><td>H24</td><td>0.935191</td><td>0.789373</td><td>0.236398</td><td>0.032*</td></tr><tr><td>C25</td><td>0.9100 (2)</td><td>0.93004 (15)</td><td>0.30511 (12)</td><td>0.0263 (4)</td></tr><tr><td>H25</td><td>0.928651</td><td>0.981009</td><td>0.263482</td><td>0.032*</td></tr><tr><td>C26</td><td>0.8782 (3)</td><td>0.96852 (15)</td><td>0.38298 (12)</td><td>0.0282 (4)</td></tr><tr><td>H26</td><td>0.875491</td><td>1.046330</td><td>0.394494</td><td>0.034*</td></tr><tr><td>C27</td><td>0.8504 (2)</td><td>0.89423 (15)</td><td>0.44383 (12)</td><td>0.0249 (4)</td></tr><tr><td>H27</td><td>0.827706</td><td>0.921163</td><td>0.496514</td><td>0.030*</td></tr><tr><td>S2A</td><td>0.27650 (7)</td><td>-0.03230 (4)</td><td>0.18957 (3)</td><td>0.0311 (2)</td><td>0.923 (2)</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>S1</td><td>0.0292 (3)</td><td>0.0456 (3)</td><td>0.0294 (3)</td><td>-0.0002 (2)</td><td>0.0125 (2)</td><td>0.0054 (2)</td></tr><tr><td>O3</td><td>0.0404 (9)</td><td>0.0513 (9)</td><td>0.0348 (8)</td><td>-0.0005 (7)</td><td>0.0204 (7)</td><td>0.0073 (7)</td></tr></tbody></table>
<table><tr><td>C28</td><td>0.0405 (13)</td><td>0.0682 (16)</td><td>0.0404 (12)</td><td>-0.0102 (11)</td><td>0.0199 (10)</td><td>-0.0153 (11)</td></tr><tr><td>C29</td><td>0.0425 (13)</td><td>0.0502 (13)</td><td>0.0367 (11)</td><td>-0.0112 (10)</td><td>0.0071 (9)</td><td>0.0057 (9)</td></tr><tr><td>S2B</td><td>0.090 (8)</td><td>0.054 (5)</td><td>0.070 (6)</td><td>0.017 (5)</td><td>0.036 (5)</td><td>0.020 (4)</td></tr><tr><td>O2</td><td>0.0324 (8)</td><td>0.0449 (8)</td><td>0.0410 (8)</td><td>0.0102 (6)</td><td>0.0057 (6)</td><td>0.0068 (6)</td></tr><tr><td>C30</td><td>0.0325 (11)</td><td>0.0456 (12)</td><td>0.0416 (11)</td><td>0.0012 (9)</td><td>0.0047 (9)</td><td>0.0100 (9)</td></tr><tr><td>C31</td><td>0.0444 (13)</td><td>0.0469 (13)</td><td>0.0530 (14)</td><td>0.0112 (10)</td><td>0.0232 (11)</td><td>0.0073 (10)</td></tr><tr><td>O1</td><td>0.0341 (8)</td><td>0.0606 (10)</td><td>0.0244 (7)</td><td>-0.0034 (7)</td><td>0.0108 (6)</td><td>0.0096 (6)</td></tr><tr><td>N1</td><td>0.0204 (7)</td><td>0.0212 (7)</td><td>0.0262 (7)</td><td>0.0000 (5)</td><td>0.0083 (6)</td><td>0.0038 (5)</td></tr><tr><td>N2</td><td>0.0216 (7)</td><td>0.0212 (7)</td><td>0.0227 (7)</td><td>0.0003 (5)</td><td>0.0086 (5)</td><td>0.0029 (5)</td></tr><tr><td>N3</td><td>0.0176 (7)</td><td>0.0211 (7)</td><td>0.0230 (7)</td><td>0.0011 (5)</td><td>0.0076 (5)</td><td>0.0029 (5)</td></tr><tr><td>N4</td><td>0.0197 (7)</td><td>0.0215 (7)</td><td>0.0233 (7)</td><td>0.0002 (5)</td><td>0.0084 (5)</td><td>0.0020 (5)</td></tr><tr><td>N5</td><td>0.0214 (7)</td><td>0.0245 (7)</td><td>0.0238 (7)</td><td>0.0008 (6)</td><td>0.0082 (6)</td><td>-0.0001 (5)</td></tr><tr><td>C1</td><td>0.0282 (10)</td><td>0.0352 (9)</td><td>0.0244 (9)</td><td>0.0044 (8)</td><td>0.0106 (7)</td><td>0.0065 (7)</td></tr><tr><td>C2</td><td>0.0205 (9)</td><td>0.0300 (9)</td><td>0.0286 (9)</td><td>0.0014 (7)</td><td>0.0105 (7)</td><td>0.0056 (7)</td></tr><tr><td>C3</td><td>0.0167 (8)</td><td>0.0250 (8)</td><td>0.0253 (8)</td><td>0.0029 (6)</td><td>0.0073 (6)</td><td>0.0030 (6)</td></tr><tr><td>C4</td><td>0.0182 (8)</td><td>0.0227 (8)</td><td>0.0230 (8)</td><td>0.0029 (6)</td><td>0.0077 (6)</td><td>0.0029 (6)</td></tr><tr><td>C5</td><td>0.0192 (8)</td><td>0.0266 (8)</td><td>0.0268 (8)</td><td>0.0000 (6)</td><td>0.0080 (7)</td><td>0.0018 (6)</td></tr><tr><td>C6</td><td>0.0231 (9)</td><td>0.0345 (9)</td><td>0.0248 (9)</td><td>0.0018 (7)</td><td>0.0043 (7)</td><td>0.0013 (7)</td></tr><tr><td>C7</td><td>0.0114 (7)</td><td>0.0240 (8)</td><td>0.0236 (8)</td><td>0.0023 (6)</td><td>0.0061 (6)</td><td>0.0037 (6)</td></tr><tr><td>C8</td><td>0.0133 (7)</td><td>0.0228 (8)</td><td>0.0239 (8)</td><td>0.0009 (6)</td><td>0.0078 (6)</td><td>0.0040 (6)</td></tr><tr><td>C9</td><td>0.0169 (8)</td><td>0.0228 (8)</td><td>0.0253 (8)</td><td>0.0015 (6)</td><td>0.0068 (6)</td><td>0.0034 (6)</td></tr><tr><td>C10</td><td>0.0239 (9)</td><td>0.0236 (8)</td><td>0.0274 (8)</td><td>0.0003 (7)</td><td>0.0099 (7)</td><td>0.0043 (7)</td></tr><tr><td>C11</td><td>0.0153 (7)</td><td>0.0225 (8)</td><td>0.0221 (8)</td><td>0.0016 (6)</td><td>0.0058 (6)</td><td>0.0024 (6)</td></tr><tr><td>C12</td><td>0.0128 (7)</td><td>0.0223 (8)</td><td>0.0241 (8)</td><td>0.0006 (6)</td><td>0.0063 (6)</td><td>0.0031 (6)</td></tr><tr><td>C13</td><td>0.0142 (7)</td><td>0.0237 (8)</td><td>0.0228 (8)</td><td>0.0014 (6)</td><td>0.0068 (6)</td><td>0.0021 (6)</td></tr><tr><td>C14</td><td>0.0178 (8)</td><td>0.0247 (8)</td><td>0.0246 (8)</td><td>0.0014 (6)</td><td>0.0070 (6)</td><td>0.0018 (6)</td></tr><tr><td>C15</td><td>0.0267 (9)</td><td>0.0280 (8)</td><td>0.0267 (9)</td><td>0.0008 (7)</td><td>0.0119 (7)</td><td>-0.0010 (7)</td></tr><tr><td>C16</td><td>0.0166 (8)</td><td>0.0253 (8)</td><td>0.0234 (8)</td><td>-0.0015 (6)</td><td>0.0066 (6)</td><td>-0.0004 (6)</td></tr><tr><td>C17</td><td>0.0262 (9)</td><td>0.0276 (9)</td><td>0.0280 (9)</td><td>0.0017 (7)</td><td>0.0101 (7)</td><td>0.0005 (7)</td></tr><tr><td>C18</td><td>0.0292 (10)</td><td>0.0357 (10)</td><td>0.0295 (9)</td><td>-0.0002 (8)</td><td>0.0114 (8)</td><td>-0.0041 (8)</td></tr><tr><td>C19</td><td>0.0257 (9)</td><td>0.0450 (11)</td><td>0.0226 (8)</td><td>-0.0037 (8)</td><td>0.0093 (7)</td><td>0.0001 (7)</td></tr><tr><td>C20</td><td>0.0256 (9)</td><td>0.0358 (10)</td><td>0.0263 (9)</td><td>-0.0026 (7)</td><td>0.0059 (7)</td><td>0.0063 (7)</td></tr><tr><td>C21</td><td>0.0213 (9)</td><td>0.0291 (9)</td><td>0.0253 (8)</td><td>-0.0002 (7)</td><td>0.0063 (7)</td><td>0.0024 (7)</td></tr><tr><td>C22</td><td>0.0133 (7)</td><td>0.0236 (8)</td><td>0.0262 (8)</td><td>0.0003 (6)</td><td>0.0068 (6)</td><td>0.0049 (6)</td></tr><tr><td>C23</td><td>0.0213 (8)</td><td>0.0230 (8)</td><td>0.0293 (9)</td><td>-0.0004 (6)</td><td>0.0099 (7)</td><td>0.0020 (7)</td></tr><tr><td>C24</td><td>0.0241 (9)</td><td>0.0297 (9)</td><td>0.0279 (9)</td><td>0.0003 (7)</td><td>0.0100 (7)</td><td>0.0037 (7)</td></tr><tr><td>C25</td><td>0.0225 (9)</td><td>0.0271 (8)</td><td>0.0305 (9)</td><td>0.0007 (7)</td><td>0.0074 (7)</td><td>0.0085 (7)</td></tr><tr><td>C26</td><td>0.0300 (10)</td><td>0.0223 (8)</td><td>0.0334 (10)</td><td>0.0026 (7)</td><td>0.0084 (8)</td><td>0.0039 (7)</td></tr><tr><td>C27</td><td>0.0235 (9)</td><td>0.0242 (8)</td><td>0.0281 (9)</td><td>0.0027 (6)</td><td>0.0071 (7)</td><td>0.0019 (7)</td></tr><tr><td>S2A</td><td>0.0253 (3)</td><td>0.0306 (3)</td><td>0.0386 (3)</td><td>0.0008 (2)</td><td>0.0087 (2)</td><td>0.0047 (2)</td></tr></table>

Geometric parameters (Å, °)

<table><tr><td>S1—O3</td><td>1.5073 (15)</td><td>C3—H3</td><td>0.9500</td></tr><tr><td>S1—C28</td><td>1.779 (2)</td><td>C3—C4</td><td>1.398 (3)</td></tr><tr><td>S1—C29</td><td>1.785 (2)</td><td>C4—C5</td><td>1.404 (2)</td></tr><tr><td>C28—H28A</td><td>0.9800</td><td>C4—C7</td><td>1.478 (2)</td></tr><tr><td>C28—H28B</td><td>0.9800</td><td>C5—H5</td><td>0.9500</td></tr></table>
<table>
  <tbody>
    <tr>
      <td>C28—H28C</td>
      <td>0.9800</td>
      <td>C5—C6</td>
      <td>1.379 (3)</td>
    </tr>
    <tr>
      <td>C29—H29A</td>
      <td>0.9800</td>
      <td>C6—H6</td>
      <td>0.9500</td>
    </tr>
    <tr>
      <td>C29—H29B</td>
      <td>0.9800</td>
      <td>C7—C8</td>
      <td>1.412 (2)</td>
    </tr>
    <tr>
      <td>C29—H29C</td>
      <td>0.9800</td>
      <td>C7—C13</td>
      <td>1.403 (2)</td>
    </tr>
    <tr>
      <td>S2B—O2</td>
      <td>1.476 (8)</td>
      <td>C8—C9</td>
      <td>1.444 (2)</td>
    </tr>
    <tr>
      <td>S2B—C30</td>
      <td>1.774 (6)</td>
      <td>C8—C11</td>
      <td>1.424 (2)</td>
    </tr>
    <tr>
      <td>S2B—C31</td>
      <td>1.766 (7)</td>
      <td>C9—C10</td>
      <td>1.492 (2)</td>
    </tr>
    <tr>
      <td>O2—S2A</td>
      <td>1.4989 (15)</td>
      <td>C10—H10A</td>
      <td>0.9800</td>
    </tr>
    <tr>
      <td>C30—H30D</td>
      <td>0.9800</td>
      <td>C10—H10B</td>
      <td>0.9800</td>
    </tr>
    <tr>
      <td>C30—H30E</td>
      <td>0.9800</td>
      <td>C10—H10C</td>
      <td>0.9800</td>
    </tr>
    <tr>
      <td>C30—H30F</td>
      <td>0.9800</td>
      <td>C12—C13</td>
      <td>1.421 (2)</td>
    </tr>
    <tr>
      <td>C30—H30A</td>
      <td>0.9800</td>
      <td>C13—C14</td>
      <td>1.441 (2)</td>
    </tr>
    <tr>
      <td>C30—H30B</td>
      <td>0.9800</td>
      <td>C14—C15</td>
      <td>1.495 (2)</td>
    </tr>
    <tr>
      <td>C30—H30C</td>
      <td>0.9800</td>
      <td>C15—H15A</td>
      <td>0.9800</td>
    </tr>
    <tr>
      <td>C30—S2A</td>
      <td>1.778 (2)</td>
      <td>C15—H15B</td>
      <td>0.9800</td>
    </tr>
    <tr>
      <td>C31—H31D</td>
      <td>0.9800</td>
      <td>C15—H15C</td>
      <td>0.9800</td>
    </tr>
    <tr>
      <td>C31—H31E</td>
      <td>0.9800</td>
      <td>C16—C17</td>
      <td>1.400 (2)</td>
    </tr>
    <tr>
      <td>C31—H31F</td>
      <td>0.9800</td>
      <td>C16—C21</td>
      <td>1.392 (2)</td>
    </tr>
    <tr>
      <td>C31—H31A</td>
      <td>0.9800</td>
      <td>C17—H17</td>
      <td>0.9500</td>
    </tr>
    <tr>
      <td>C31—H31B</td>
      <td>0.9800</td>
      <td>C17—C18</td>
      <td>1.385 (3)</td>
    </tr>
    <tr>
      <td>C31—H31C</td>
      <td>0.9800</td>
      <td>C18—H18</td>
      <td>0.9500</td>
    </tr>
    <tr>
      <td>C31—S2A</td>
      <td>1.797 (2)</td>
      <td>C18—C19</td>
      <td>1.390 (3)</td>
    </tr>
    <tr>
      <td>O1—H1</td>
      <td>0.8400</td>
      <td>C19—H19</td>
      <td>0.9500</td>
    </tr>
    <tr>
      <td>O1—C1</td>
      <td>1.357 (2)</td>
      <td>C19—C20</td>
      <td>1.390 (3)</td>
    </tr>
    <tr>
      <td>N1—N2</td>
      <td>1.3815 (19)</td>
      <td>C20—H20</td>
      <td>0.9500</td>
    </tr>
    <tr>
      <td>N1—C9</td>
      <td>1.314 (2)</td>
      <td>C20—C21</td>
      <td>1.391 (3)</td>
    </tr>
    <tr>
      <td>N2—C11</td>
      <td>1.371 (2)</td>
      <td>C21—H21</td>
      <td>0.9500</td>
    </tr>
    <tr>
      <td>N2—C16</td>
      <td>1.414 (2)</td>
      <td>C22—C23</td>
      <td>1.390 (2)</td>
    </tr>
    <tr>
      <td>N3—C11</td>
      <td>1.336 (2)</td>
      <td>C22—C27</td>
      <td>1.394 (2)</td>
    </tr>
    <tr>
      <td>N3—C12</td>
      <td>1.340 (2)</td>
      <td>C23—H23</td>
      <td>0.9500</td>
    </tr>
    <tr>
      <td>N4—N5</td>
      <td>1.3880 (19)</td>
      <td>C23—C24</td>
      <td>1.392 (2)</td>
    </tr>
    <tr>
      <td>N4—C12</td>
      <td>1.375 (2)</td>
      <td>C24—H24</td>
      <td>0.9500</td>
    </tr>
    <tr>
      <td>N4—C22</td>
      <td>1.418 (2)</td>
      <td>C24—C25</td>
      <td>1.386 (3)</td>
    </tr>
    <tr>
      <td>N5—C14</td>
      <td>1.313 (2)</td>
      <td>C25—H25</td>
      <td>0.9500</td>
    </tr>
    <tr>
      <td>C1—C2</td>
      <td>1.396 (3)</td>
      <td>C25—C26</td>
      <td>1.394 (3)</td>
    </tr>
    <tr>
      <td>C1—C6</td>
      <td>1.392 (3)</td>
      <td>C26—H26</td>
      <td>0.9500</td>
    </tr>
    <tr>
      <td>C2—H2</td>
      <td>0.9500</td>
      <td>C26—C27</td>
      <td>1.388 (3)</td>
    </tr>
    <tr>
      <td>C2—C3</td>
      <td>1.382 (2)</td>
      <td>C27—H27</td>
      <td>0.9500</td>
    </tr>
    <tr>
      <td>O3—S1—C28</td>
      <td>106.42 (12)</td>
      <td>C13—C7—C4</td>
      <td>121.55 (15)</td>
    </tr>
    <tr>
      <td>O3—S1—C29</td>
      <td>105.77 (10)</td>
      <td>C13—C7—C8</td>
      <td>114.37 (15)</td>
    </tr>
    <tr>
      <td>C28—S1—C29</td>
      <td>97.04 (12)</td>
      <td>C7—C8—C9</td>
      <td>136.98 (16)</td>
    </tr>
    <tr>
      <td>S1—C28—H28A</td>
      <td>109.5</td>
      <td>C7—C8—C11</td>
      <td>118.89 (15)</td>
    </tr>
    <tr>
      <td>S1—C28—H28B</td>
      <td>109.5</td>
      <td>C11—C8—C9</td>
      <td>104.04 (14)</td>
    </tr>
    <tr>
      <td>S1—C28—H28C</td>
      <td>109.5</td>
      <td>N1—C9—C8</td>
      <td>110.94 (14)</td>
    </tr>
    <tr>
      <td>H28A—C28—H28B</td>
      <td>109.5</td>
      <td>N1—C9—C10</td>
      <td>118.63 (15)</td>
    </tr>
    <tr>
      <td>H28A—C28—H28C</td>
      <td>109.5</td>
      <td>C8—C9—C10</td>
      <td>130.43 (15)</td>
    </tr>
    <tr>
      <td>H28B—C28—H28C</td>
      <td>109.5</td>
      <td>C9—C10—H10A</td>
      <td>109.5</td>
    </tr>
  </tbody>
</table>
<table>
  <tbody>
    <tr>
      <td>S1—C29—H29A</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S1—C29—H29B</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S1—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>O2—S2B—C30</td>
      <td>108.5 (4)</td>
    </tr>
    <tr>
      <td>O2—S2B—C31</td>
      <td>109.0 (5)</td>
    </tr>
    <tr>
      <td>C31—S2B—C30</td>
      <td>98.6 (4)</td>
    </tr>
    <tr>
      <td>S2B—C30—H30D</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S2B—C30—H30E</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S2B—C30—H30F</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H30D—C30—H30E</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H30D—C30—H30F</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H30E—C30—H30F</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H30A—C30—H30B</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H30A—C30—H30C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H30B—C30—H30C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S2A—C30—H30A</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S2A—C30—H30B</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S2A—C30—H30C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S2B—C31—H31D</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S2B—C31—H31E</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S2B—C31—H31F</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H31D—C31—H31E</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H31D—C31—H31F</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H31E—C31—H31F</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H31A—C31—H31B</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H31A—C31—H31C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H31B—C31—H31C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S2A—C31—H31A</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S2A—C31—H31B</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>S2A—C31—H31C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>C1—O1—H1</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>C9—N1—N2</td>
      <td>107.49 (14)</td>
    </tr>
    <tr>
      <td>N1—N2—C16</td>
      <td>119.75 (14)</td>
    </tr>
    <tr>
      <td>C11—N2—N1</td>
      <td>110.67 (14)</td>
    </tr>
    <tr>
      <td>C11—N2—C16</td>
      <td>129.57 (15)</td>
    </tr>
    <tr>
      <td>C11—N3—C12</td>
      <td>110.69 (14)</td>
    </tr>
    <tr>
      <td>N5—N4—C22</td>
      <td>118.97 (14)</td>
    </tr>
    <tr>
      <td>C12—N4—N5</td>
      <td>110.26 (13)</td>
    </tr>
    <tr>
      <td>C12—N4—C22</td>
      <td>130.64 (15)</td>
    </tr>
    <tr>
      <td>C14—N5—N4</td>
      <td>107.39 (14)</td>
    </tr>
    <tr>
      <td>O1—C1—C2</td>
      <td>122.12 (18)</td>
    </tr>
    <tr>
      <td>O1—C1—C6</td>
      <td>118.24 (17)</td>
    </tr>
    <tr>
      <td>C6—C1—C2</td>
      <td>119.63 (17)</td>
    </tr>
    <tr>
      <td>C1—C2—H2</td>
      <td>120.0</td>
    </tr>
    <tr>
      <td>C3—C2—C1</td>
      <td>119.95 (17)</td>
    </tr>
  </tbody>
</table>

<table>
  <tbody>
    <tr>
      <td>C9—C10—H10B</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>C9—C10—H10C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H10A—C10—H10B</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H10A—C10—H10C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H10B—C10—H10C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>N2—C11—C8</td>
      <td>106.84 (14)</td>
    </tr>
    <tr>
      <td>N3—C11—N2</td>
      <td>124.68 (15)</td>
    </tr>
    <tr>
      <td>N3—C11—C8</td>
      <td>128.41 (15)</td>
    </tr>
    <tr>
      <td>N3—C12—N4</td>
      <td>125.47 (15)</td>
    </tr>
    <tr>
      <td>N3—C12—C13</td>
      <td>127.44 (15)</td>
    </tr>
    <tr>
      <td>N4—C12—C13</td>
      <td>107.05 (14)</td>
    </tr>
    <tr>
      <td>C7—C13—C12</td>
      <td>120.07 (15)</td>
    </tr>
    <tr>
      <td>C7—C13—C14</td>
      <td>135.79 (16)</td>
    </tr>
    <tr>
      <td>C12—C13—C14</td>
      <td>104.08 (15)</td>
    </tr>
    <tr>
      <td>N5—C14—C13</td>
      <td>111.18 (15)</td>
    </tr>
    <tr>
      <td>N5—C14—C15</td>
      <td>119.08 (15)</td>
    </tr>
    <tr>
      <td>C13—C14—C15</td>
      <td>129.67 (16)</td>
    </tr>
    <tr>
      <td>C14—C15—H15A</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>C14—C15—H15B</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>C14—C15—H15C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H15A—C15—H15B</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H15A—C15—H15C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>H15B—C15—H15C</td>
      <td>109.5</td>
    </tr>
    <tr>
      <td>C17—C16—N2</td>
      <td>118.88 (16)</td>
    </tr>
    <tr>
      <td>C21—C16—N2</td>
      <td>120.89 (15)</td>
    </tr>
    <tr>
      <td>C21—C16—C17</td>
      <td>120.22 (16)</td>
    </tr>
    <tr>
      <td>C16—C17—H17</td>
      <td>120.3</td>
    </tr>
    <tr>
      <td>C18—C17—C16</td>
      <td>119.42 (17)</td>
    </tr>
    <tr>
      <td>C18—C17—H17</td>
      <td>120.3</td>
    </tr>
    <tr>
      <td>C17—C18—H18</td>
      <td>119.6</td>
    </tr>
    <tr>
      <td>C17—C18—C19</td>
      <td>120.79 (18)</td>
    </tr>
    <tr>
      <td>C19—C18—H18</td>
      <td>119.6</td>
    </tr>
    <tr>
      <td>C18—C19—H19</td>
      <td>120.3</td>
    </tr>
    <tr>
      <td>C18—C19—C20</td>
      <td>119.44 (18)</td>
    </tr>
    <tr>
      <td>C20—C19—H19</td>
      <td>120.3</td>
    </tr>
    <tr>
      <td>C19—C20—H20</td>
      <td>119.7</td>
    </tr>
    <tr>
      <td>C19—C20—C21</td>
      <td>120.61 (18)</td>
    </tr>
    <tr>
      <td>C21—C20—H20</td>
      <td>119.7</td>
    </tr>
    <tr>
      <td>C16—C21—H21</td>
      <td>120.2</td>
    </tr>
    <tr>
      <td>C20—C21—C16</td>
      <td>119.50 (17)</td>
    </tr>
    <tr>
      <td>C20—C21—H21</td>
      <td>120.2</td>
    </tr>
    <tr>
      <td>C23—C22—N4</td>
      <td>121.06 (15)</td>
    </tr>
    <tr>
      <td>C23—C22—C27</td>
      <td>119.85 (16)</td>
    </tr>
    <tr>
      <td>C27—C22—N4</td>
      <td>119.08 (16)</td>
    </tr>
    <tr>
      <td>C22—C23—H23</td>
      <td>120.2</td>
    </tr>
    <tr>
      <td>C22—C23—C24</td>
      <td>119.68 (16)</td>
    </tr>
    <tr>
      <td>C24—C23—H23</td>
      <td>120.2</td>
    </tr>
    <tr>
      <td>C23—C24—H24</td>
      <td>119.5</td>
    </tr>
  </tbody>
</table>
<table><tr><td>C3—C2—H2</td><td>120.0</td></tr><tr><td>C2—C3—H3</td><td>119.4</td></tr><tr><td>C2—C3—C4</td><td>121.17 (16)</td></tr><tr><td>C4—C3—H3</td><td>119.4</td></tr><tr><td>C3—C4—C5</td><td>117.97 (16)</td></tr><tr><td>C3—C4—C7</td><td>122.29 (15)</td></tr><tr><td>C5—C4—C7</td><td>119.72 (15)</td></tr><tr><td>C4—C5—H5</td><td>119.4</td></tr><tr><td>C6—C5—C4</td><td>121.24 (17)</td></tr><tr><td>C6—C5—H5</td><td>119.4</td></tr><tr><td>C1—C6—H6</td><td>120.0</td></tr><tr><td>C5—C6—C1</td><td>119.97 (16)</td></tr><tr><td>C5—C6—H6</td><td>120.0</td></tr><tr><td>C8—C7—C4</td><td>124.05 (15)</td></tr></table>

<table><tr><td>O1—C1—C2—C3</td><td>179.40 (17)</td></tr><tr><td>O1—C1—C6—C5</td><td>-178.02 (17)</td></tr><tr><td>N1—N2—C11—N3</td><td>176.07 (15)</td></tr><tr><td>N1—N2—C11—C8</td><td>-1.05 (18)</td></tr><tr><td>N1—N2—C16—C17</td><td>-28.3 (2)</td></tr><tr><td>N1—N2—C16—C21</td><td>151.19 (16)</td></tr><tr><td>N2—N1—C9—C8</td><td>0.16 (18)</td></tr><tr><td>N2—N1—C9—C10</td><td>179.80 (14)</td></tr><tr><td>N2—C16—C17—C18</td><td>179.88 (16)</td></tr><tr><td>N2—C16—C21—C20</td><td>179.48 (16)</td></tr><tr><td>N3—C12—C13—C7</td><td>1.7 (3)</td></tr><tr><td>N3—C12—C13—C14</td><td>-175.87 (16)</td></tr><tr><td>N4—N5—C14—C13</td><td>-0.10 (19)</td></tr><tr><td>N4—N5—C14—C15</td><td>-177.42 (14)</td></tr><tr><td>N4—C12—C13—C7</td><td>179.44 (14)</td></tr><tr><td>N4—C12—C13—C14</td><td>1.83 (17)</td></tr><tr><td>N4—C22—C23—C24</td><td>179.77 (15)</td></tr><tr><td>N4—C22—C27—C26</td><td>179.89 (15)</td></tr><tr><td>N5—N4—C12—N3</td><td>175.74 (15)</td></tr><tr><td>N5—N4—C12—C13</td><td>-2.01 (17)</td></tr><tr><td>N5—N4—C22—C23</td><td>173.13 (15)</td></tr><tr><td>N5—N4—C22—C27</td><td>-7.5 (2)</td></tr><tr><td>C1—C2—C3—C4</td><td>-1.1 (3)</td></tr><tr><td>C2—C1—C6—C5</td><td>2.6 (3)</td></tr><tr><td>C2—C3—C4—C5</td><td>2.0 (3)</td></tr><tr><td>C2—C3—C4—C7</td><td>-176.14 (16)</td></tr><tr><td>C3—C4—C5—C6</td><td>-0.6 (3)</td></tr><tr><td>C3—C4—C7—C8</td><td>-57.1 (2)</td></tr><tr><td>C3—C4—C7—C13</td><td>124.85 (18)</td></tr><tr><td>C4—C5—C6—C1</td><td>-1.7 (3)</td></tr><tr><td>C4—C7—C8—C9</td><td>-0.1 (3)</td></tr><tr><td>C4—C7—C8—C11</td><td>-175.98 (14)</td></tr><tr><td>C4—C7—C13—C12</td><td>174.76 (14)</td></tr></table>

<table><tr><td>C25—C24—C23</td><td>120.94 (17)</td></tr><tr><td>C25—C24—H24</td><td>119.5</td></tr><tr><td>C24—C25—H25</td><td>120.5</td></tr><tr><td>C24—C25—C26</td><td>119.00 (17)</td></tr><tr><td>C26—C25—H25</td><td>120.5</td></tr><tr><td>C25—C26—H26</td><td>119.7</td></tr><tr><td>C27—C26—C25</td><td>120.62 (17)</td></tr><tr><td>C27—C26—H26</td><td>119.7</td></tr><tr><td>C22—C27—H27</td><td>120.1</td></tr><tr><td>C26—C27—C22</td><td>119.90 (17)</td></tr><tr><td>C26—C27—H27</td><td>120.1</td></tr><tr><td>O2—S2A—C30</td><td>107.23 (10)</td></tr><tr><td>O2—S2A—C31</td><td>106.38 (10)</td></tr><tr><td>C30—S2A—C31</td><td>97.34 (12)</td></tr></table>

<table><tr><td>C7—C8—C11—N3</td><td>1.2 (3)</td></tr><tr><td>C7—C13—C14—N5</td><td>-178.12 (18)</td></tr><tr><td>C7—C13—C14—C15</td><td>-1.2 (3)</td></tr><tr><td>C8—C7—C13—C12</td><td>-3.5 (2)</td></tr><tr><td>C8—C7—C13—C14</td><td>173.18 (18)</td></tr><tr><td>C9—N1—N2—C11</td><td>0.57 (18)</td></tr><tr><td>C9—N1—N2—C16</td><td>179.90 (14)</td></tr><tr><td>C9—C8—C11—N2</td><td>1.07 (17)</td></tr><tr><td>C9—C8—C11—N3</td><td>-175.91 (16)</td></tr><tr><td>C11—N2—C16—C17</td><td>150.91 (18)</td></tr><tr><td>C11—N2—C16—C21</td><td>-29.6 (3)</td></tr><tr><td>C11—N3—C12—N4</td><td>-175.80 (15)</td></tr><tr><td>C11—N3—C12—C13</td><td>1.5 (2)</td></tr><tr><td>C11—C8—C9—N1</td><td>-0.77 (18)</td></tr><tr><td>C11—C8—C9—C10</td><td>179.64 (16)</td></tr><tr><td>C12—N3—C11—N2</td><td>-179.45 (15)</td></tr><tr><td>C12—N3—C11—C8</td><td>-3.0 (2)</td></tr><tr><td>C12—N4—N5—C14</td><td>1.33 (18)</td></tr><tr><td>C12—N4—C22—C23</td><td>-11.4 (3)</td></tr><tr><td>C12—N4—C22—C27</td><td>168.02 (16)</td></tr><tr><td>C12—C13—C14—N5</td><td>-1.08 (19)</td></tr><tr><td>C12—C13—C14—C15</td><td>175.87 (17)</td></tr><tr><td>C13—C7—C8—C9</td><td>178.09 (18)</td></tr><tr><td>C13—C7—C8—C11</td><td>2.2 (2)</td></tr><tr><td>C16—N2—C11—N3</td><td>-3.2 (3)</td></tr><tr><td>C16—N2—C11—C8</td><td>179.71 (15)</td></tr><tr><td>C16—C17—C18—C19</td><td>0.5 (3)</td></tr><tr><td>C17—C16—C21—C20</td><td>-1.1 (3)</td></tr><tr><td>C17—C18—C19—C20</td><td>-0.7 (3)</td></tr><tr><td>C18—C19—C20—C21</td><td>0.0 (3)</td></tr><tr><td>C19—C20—C21—C16</td><td>0.8 (3)</td></tr><tr><td>C21—C16—C17—C18</td><td>0.4 (3)</td></tr><tr><td>C22—N4—N5—C14</td><td>177.67 (14)</td></tr></table>
<table><caption>Hydrogen-bond geometry (Å, °)</caption><tr><td>C4—C7—C13—C14</td><td>-8.6 (3)</td><td>C22—N4—C12—N3</td><td>0.0 (3)</td></tr><tr><td>C5—C4—C7—C8</td><td>124.86 (18)</td><td>C22—N4—C12—C13</td><td>-177.79 (15)</td></tr><tr><td>C5—C4—C7—C13</td><td>-53.2 (2)</td><td>C22—C23—C24—C25</td><td>0.1 (3)</td></tr><tr><td>C6—C1—C2—C3</td><td>-1.3 (3)</td><td>C23—C22—C27—C26</td><td>-0.7 (3)</td></tr><tr><td>C7—C4—C5—C6</td><td>177.57 (16)</td><td>C23—C24—C25—C26</td><td>-0.2 (3)</td></tr><tr><td>C7—C8—C9—N1</td><td>-177.03 (18)</td><td>C24—C25—C26—C27</td><td>-0.2 (3)</td></tr><tr><td>C7—C8—C9—C10</td><td>3.4 (3)</td><td>C25—C26—C27—C22</td><td>0.6 (3)</td></tr><tr><td>C7—C8—C11—N2</td><td>178.16 (14)</td><td>C27—C22—C23—C24</td><td>0.4 (3)</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>C19—H19···O1<sup>i</sup></td><td>0.95</td><td>2.37</td><td>3.283 (2)</td><td>160</td></tr><tr><td>C29—H29B···O2<sup>ii</sup></td><td>0.98</td><td>2.48</td><td>3.312 (3)</td><td>142</td></tr></tbody></table>

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