Synthesis, crystal structures and Hirshfeld surface
analysis of
1,4-dibenzyl-6-methyl-1,4-dihydroquinoxaline-2,3-dione

Emine Berrin Cinar, Ayman Zouitini, Youssef Kandri Rodi, Younes Ouzidan,
Jérôme Marrot, Damien Prim, Necmi Dege, Eiad Saif

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To cite this version:

Emine Berrin Cinar, Ayman Zouitini, Youssef Kandri Rodi, Younes Ouzidan, Jérôme Marrot, et al. Synthesis, crystal structures and Hirshfeld surface analysis of 1,4-dibenzyl-6-methyl-1,4-dihydroquinoxaline-2,3-dione. Acta crystallographica Section E: Crystallographic communications [2015-..], 2023, 76 (8), pp.1361-1364. 10.1107/S2056989020009895. hal-03119315

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Acta Cryst.

E

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN 2056-9890

Received 16 June 2020

Accepted 19 July 2020

Edited by J. T. Mague, Tulane University, USA

**Keywords:** crystal structure; Hirshfeld surfaces; quinoxaline; hydrogen bonding.

CCDC reference: 1936664

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

# Synthesis, crystal structures and Hirshfeld surface analysis of 1,4-dibenzyl-6-methyl-1,4-dihydro-quinoxaline-2,3-dione

Emine Berrin Cinar,ª Ayman Zouitini,ᵇ Youssef Kandri Rodi,ᵇ Younes Ouzidan,ᶜ Jérôme Marrot,ᵈ Damien Prim,ᵈ* Necmi Degeª and Eiad Saifeª

The title quinoxaline molecule, C₂₃H₂₀N₂O₂, is not planar, the dihedral angle between the mean planes of the benzene rings being 72.54 (15)°. In the crystal, molecules are connected into chains extending parallel to (101) by weak C—H···O hydrogen bonds. Weak C—H···π interactions link the chains, forming a three-dimensional network structure. Hirshfeld surface analysis revealed that the most important contributions for the crystal packing are from H···H (48.7%), H···C/C···H (32.0%), H···O/O···H (15.4%), C···C (1.9%), H···N/N···H (1.1%) contacts.

## 1. Chemical context

Given their importance in the pharmaceutical, chemical and industrial fields, the synthesis of quinoxaline and its derivatives has been a goal of chemists in recent years. Quinoxaline derivatives find use as anticancer (Noolvi *et al.*, 2011), antimalarial (Guillon *et al.*, 2004), antifungal (Xu & Fan, 2011), antiviral (Cai *et al.*, 2008) and anti-inflammatory (Yan *et al.*, 2007) agents. Some quinoxaline derivatives have also been reported to be corrosion inhibitors for steel in an acidic medium (Zouitini *et al.*, 2018, 2019; El Janati *et al.*, 2020). In this work, we report the synthesis and structure of the title compound obtained by the action of benzyl chloride on 6-methyl-1,4-dihydroquinoxaline-2,3-dione in the presence of potassium carbonate and a catalytic quantity of tetra-*n*-butylammonium bromide. A Hirshfeld surface analysis was also performed.

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OPEN ACCESS

<footnote>ªDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, Samsun, 55200, Turkey, ᵇLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, BP 2202, Fez, Morocco, ᶜLaboratoire de Chimie Physique et Chimie Bio-organique, Faculté des Sciences et Techniques Mohammed Media, Université Hassan II, Casablanca, BP 146, 28800, Mohammed Media, Morocco, ᵈInstitut Lavoisier de Versailles, UVSQ, CNRS, Université Paris-Saclay, 78035 Versailles, France, and ᵉDepartment of Computer and Electronic Engineering Technology, Sana'a Community College, Sana'a, Yemen. ᶜCorrespondence e-mail: eiad.saif2016@gmail.com</footnote>
<caption>**Table 1**
Hydrogen-bond geometry (Å, °).</caption>

Cg3 is the centroid of the C11–C16 benzene ring.

<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>C10–H10A···O2<sup>i</sup></td><td>0.97</td><td>2.52</td><td>3.251 (3)</td><td>132</td></tr><tr><td>C16–H16···O1<sup>i</sup></td><td>0.93</td><td>2.55</td><td>3.3984 (4)</td><td>152</td></tr><tr><td>C25–H25···Cg3<sup>ii</sup></td><td>0.93</td><td>2.83</td><td>3.683 (3)</td><td>153</td></tr></tbody></table>

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

## 2. Structural commentary

An ORTEPIII (Burnett & Johnson, 1996) view of the molecule is given in Fig. 1. The molecule is not planar, the dihedral angle between the mean planes of the benzene rings (C11–C16 and C24–C29) being 72.54 (15)°. The mean planes of the C1/N2/C9/C8/N1/C6 and C11–C16 rings make an angle of 73.093 (13)° while the C1–C6 and C24–C29 rings make an angle of 79.01 (14)°. The C1/N2/C9/C8/N1/C6 and C1–C6 rings are nearly coplanar, subtending a dihedral angle of only 3.07 (11)°. The C8–O1 and C9–O2 bonds show double-bond character with bond lengths of 1.222 (3) and 1.217 (3) Å, respectively. The N1–C10 and N2–C23 bond lengths are 1.476 (3) and 1.464 (3) Å, respectively while the C11–C10–N1 bond angle is 113.57 (18)° and the N2–C23–C24 bond angle is 114.05 (18)°. The C9–N2–C23–C24 and C8–N1–C10–C11 torsion angles are –96.7 (2) and –93.4 (2)°, respectively.

<figure><img src="image_7.png" /><figcaption>**Figure 1**
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level.</figcaption></figure>

<figure><img src="image_8.png" /><figcaption>**Figure 2**
View of a portion of a chain along the *a*-axis direction with C–H···O hydrogen bonds depicted by dashed lines.</figcaption></figure>

<figure><img src="image_9.png" /><figcaption>**Figure 3**
Packing viewed along the *a*-axis direction with C–H···O hydrogen bonds and C–H···π(ring) interactions depicted, respectively, by black and green dashed lines.</figcaption></figure>

## 3. Supramolecular features

In the crystal, molecules are connected by weak C16–H16···O1 and C10–H10A···O2 hydrogen bonds into chains extending parallel to (101) (Table 1 and Fig. 2). Weak C25–H25···Cg3 interactions (2.83 Å; Cg3 is the centroid of the C11–C16 ring at $-x + 2, -y, -z$) link the chains into a three-dimensional network structure (Table 1 and Fig. 3).

## 4. Hirshfeld surface analysis

The CrystalExplorer17.5 (Turner *et al.*, 2017) program was used to analyse the interactions within the crystal. The donor–acceptor groups are visualized using a standard (high) surface resolution and $d_{norm}$ surfaces mapped over a fixed colour scale of –0.140 (red) to 1.358 (blue) a.u., as illustrated in Fig. 4. Red spots on the surface of the $d_{norm}$ plot indicate intermolecular contacts involving the hydrogen bonds. The red spots identified in Fig. 4(a) correspond to the intermolecular C–H···O bonds. Regions close to the sum of the van der Waals radii are shown in white. Fig. 4(b) shows the shape-index surface, which can be used to detect the presence of π-stacking interactions.

<figure><img src="image_10.png" /><figcaption>**Figure 4**
Hirshfeld surface mapper over (a) $d_{norm}$ and (b) shape-index to visualize the interactions in the title compound.</figcaption></figure>
<figure><img src="image_11.png" /><figcaption>Figure 5</figcaption></figure>

Fingerprint plot for all interactions and those delineated into the most important interactions.

The absence of characteristic triangles indicates that no significant π-π interactions are present. Two-dimensional fingerprints were also generated in the range -1 to 1 Å (Fig. 5). As expected, H···H (48.7%) and H···C/C···H (32.0%) contacts dominate the intermolecular interactions, but the O···H/H···O contacts are important directional intermolecular interactions in the crystal. The C···C (1.9%) and H···N/N···H (1.1%) contribute minimally to the overall crystal packing.

## 5. Database survey

A search of the Cambridge Structural Database (CSD, version 5.40, update August 2019; Groom *et al.*, 2016) using 1-benzyl-3,4-dihydroquinoxalin-2-(1*H*)-one as the main skeleton revealed the presence of three structures similar to the title compound, but with different substituents. These are: 1,4,6-tribenzoyl-3-(4-bromobenzyl)-1,4-dihydroquinoxaline-2-one (LEQWIO; Abraham *et al.*, 2006), 1,4-dibenzoyl-6-trifluoromethyl-3-(4-bromobenzyl)-1,4-dihydroquinoxaline-2-one (LEQWOU; Abraham *et al.*, 2006) and 1,4-dibenzyl-6-chloro-1,4-dihydroquinoxaline-2,3-dione (PAWFEB; El Janati *et al.*, 2017). In the latter study (PAWFEB) examining compounds having the same skeletal system as the 1,4-dihydroquinoxaline-2,3-dione structure in the title compound, the corrosion inhibition efficiency of 1,4-diallyl-6-chloroquinoxaline-2,3-(1*H*,4*H*)-dione and 1,4-diallyl-6-nitroquinoxaline-2,3-(1*H*,4*H*)-dione on mild steel (MS) in 1.0 M HCl solution was investigated.

## 6. Synthesis and crystallization

To a solution of 6-methyl-1,4-dihydroquinoxaline-2,3-dione (0.3 g, 1.73 mmol) in DMF (15 mL), were added potassium carbonate (0.47 g, 3.61 mmol) and tetra-*n*-butylammonium bromide (0.07 g, 0.23 mmol). After stirring for 10 min, 0.5 mL (4.32 mmol) of benzyl chloride was added and the mixture was stirred at room temperature for 6 h. After filtration of the salts, the DMF was evaporated under reduced pressure and

<table><caption>Table 2</caption><caption>Experimental details.</caption><tbody><tr><td>Crystal data</td><td></td></tr><tr><td>Chemical formula</td><td>C<sub>23</sub>H<sub>20</sub>N<sub>2</sub>O<sub>2</sub></td></tr><tr><td>M<sub>r</sub></td><td>356.41</td></tr><tr><td>Crystal system, space group</td><td>Monoclinic, P2<sub>1</sub>/n</td></tr><tr><td>Temperature (K)</td><td>296</td></tr><tr><td>a, b, c (Å)</td><td>9.0844 (12), 18.7227 (18),<br/>11.2708 (14)</td></tr><tr><td>β (°)</td><td>104.848 (4)</td></tr><tr><td>V (Å<sup>3</sup>)</td><td>1853.0 (4)</td></tr><tr><td>Z</td><td>4</td></tr><tr><td>Radiation type</td><td>Mo Kα</td></tr><tr><td>μ (mm<sup>-1</sup>)</td><td>0.08</td></tr><tr><td>Crystal size (mm)</td><td>0.30 × 0.16 × 0.06</td></tr><tr><td>Data collection</td><td></td></tr><tr><td>Diffractometer</td><td>Bruker APEXII CCD</td></tr><tr><td>Absorption correction</td><td>Multi-scan (SADABS; Bruker,<br/>2016)</td></tr><tr><td>T<sub>min</sub>, T<sub>max</sub></td><td>0.677, 0.746</td></tr><tr><td>No. of measured, independent and<br/>observed [I > 2σ(I)] reflections</td><td>22287, 4253, 2487</td></tr><tr><td>R<sub>int</sub></td><td>0.054</td></tr><tr><td>(sin θ/λ)<sub>max</sub> (Å<sup>-1</sup>)</td><td>0.649</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>0.060, 0.188, 1.04</td></tr><tr><td>No. of reflections</td><td>4253</td></tr><tr><td>No. of parameters</td><td>244</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>0.38, -0.25</td></tr></tbody></table>

Computer programs: *APEX3* and *SAINT* (Bruker, 2016), *SHELXT20183* (Sheldrick, 2015a), *SHELXL20183* (Sheldrick, 2015b), *OLEX2* (Dolomanov *et al.*, 2009), *Mercury* (Macrae *et al.*, 2020), *WinGX* (Farrugia, 2012), *PLATON* (Spek, 2020) and *publCIF* (Westrip, 2010).

the residue obtained was dissolved in dichloromethane. The organic phase was then dried over Na₂SO₄ and concentrated. The mixture obtained was chromatographed on a silica gel column [eluent: hexane/ethylacetate (2/1)]. The crude product was recrystallized from ethanol as yellow crystals suitable for X-ray analysis (m.p. 493.5 K).

## 7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms treated as riding: C-H = 0.97 Å and Uiso(H) = 1.5Ueq(C) for methyl, C-H = 0.96 Å and Uiso(H) = 1.2Ueq(C) for methylene, C-H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic and C-H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for methine H atoms.

## Funding information

This study was supported by Ondokuz Mayıs University under project No. PYOFEN.1906.19.001.

## References

* Abraham, C. J., Paull, D. H., Scerba, M. T., Grebinski, J. W. & Lectka, T. (2006). *J. Am. Chem. Soc.* **128**, 13370-13371.

* Bruker (2016). *APEX3*, *SADABS* and *SAINT*. Bruker AXS Inc., Madison, Wisconsin, USA.

* Burnett, M. N. & Johnson, C. K. (1996). *ORTEPIII*. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Cai, J., Zou, J., Pan, X. & Zhang, W. (2008). *Tetrahedron Lett.* **49**, 7386–7390.

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

El Janati, A., Elmsellem, H., Kandri Rodi, Y., Ouzidan, Y., Ramdani, M., Mokhtari, M., Abdel-Rahman, I., Cherif Alaoui, I., Ouazzani Chahdi, F. & Kusuma, H. S. (2020). *Int. J. Corros. Scale Inhib.* **9**, 644–660.

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Guillon, J., Grellier, P., Labaied, M., Sonnet, P., Léger, J. M., Déprez-Poulain, R., Forfar-Bares, I., Dallemagne, P., Lemaître, N., Péhourcq, F., Rochette, J., Sergheraert, C. & Jarry, C. (2004). *J. Med. Chem.* **47**, 1997–2009.

Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). *J. Appl. Cryst.* **53**, 226–235.

Noolvi, M. N., Patel, H. M., Bhardwaj, V. & Chauhan, A. (2011). *Eur. J. Med. Chem.* **46**, 2327–2346.

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

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

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

Turner, M. J., Mckinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). *CrystalExplorer17.5*. The University of Western Australia.

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Zouitini, A., Kandri Rodi, Y., Elmsellem, H., Ouazzani Chahdi, F., Steli, H., Ad, C., Ouzidan, Y., Essassi, E., Chetouani, A. & Hammouti, B. (2018). *Moroc. J. Chem.* **6**, 391–403.

Zouitini, A., Kandri Rodi, Y., Ouzidan, Y., Ouazzani Chahdi, F., Mokhtari, M., Abdel-Rahman, I., Essassi, E. M., Aouniti, A., Hammouti, B. & Elmsellem, H. (2019). *Int. J. Corros. Scale Inhib.* **8**, 225–240.
supporting information

Acta Cryst. (2020). E76, 1361-1364 [https://doi.org/10.1107/S2056989020009895]

# Synthesis, crystal structures and Hirshfeld surface analysis of 1,4-dibenzyl-6-methyl-1,4-dihydroquinoxaline-2,3-dione

Emine Berrin Cinar, Ayman Zouitini, Youssef Kandri Rodi, Younes Ouzidan, Jérôme Marrot, Damien Prim, Necmi Dege and Eiad Saif

## Computing details

Data collection: *APEX3* (Bruker, 2016); cell refinement: *SAINT* (Bruker, 2016); data reduction: *SAINT* (Bruker, 2016); program(s) used to solve structure: *SHELXT2018/3* (Sheldrick, 2015a); program(s) used to refine structure: *SHELXL2018/3* (Sheldrick, 2015b); molecular graphics: *OLEX2* (Dolomanov *et al.*, 2009) and *Mercury* (Macrae *et al.*, 2020); software used to prepare material for publication: *WinGX* (Farrugia, 2012), *PLATON* (Spek, 2020), *SHELXL2018* (Sheldrick, 2015b) and *publCIF* (Westrip, 2010).

## 1,4-Dibenzyl-6-methyl-1,4-dihydroquinoxaline-2,3-dione

### Crystal data

<table><tr><td>C<sub>23</sub>H<sub>20</sub>N<sub>2</sub>O<sub>2</sub></td><td><i>F</i>(000) = 752</td></tr><tr><td><i>M</i><sub>r</sub> = 356.41</td><td><i>D</i><sub>x</sub> = 1.278 Mg m<sup>-3</sup></td></tr><tr><td>Monoclinic, <i>P</i>2<sub>1</sub>/<i>n</i></td><td>Mo Kα radiation, <i>λ</i> = 0.71073 Å</td></tr><tr><td><i>a</i> = 9.0844 (12) Å</td><td>Cell parameters from 4963 reflections</td></tr><tr><td><i>b</i> = 18.7227 (18) Å</td><td><i>θ</i> = 2.6–24.6°</td></tr><tr><td><i>c</i> = 11.2708 (14) Å</td><td><i>μ</i> = 0.08 mm<sup>-1</sup></td></tr><tr><td><i>β</i> = 104.848 (4)°</td><td><i>T</i> = 296 K</td></tr><tr><td><i>V</i> = 1853.0 (4) Å<sup>3</sup></td><td>Parallelepiped, yellow</td></tr><tr><td><i>Z</i> = 4</td><td>0.30 × 0.16 × 0.06 mm</td></tr></table>

### Data collection

<table><tr><td>Bruker APEXII CCD<br>diffractometer</td><td>4253 independent reflections<br>2487 reflections with <i>I</i> > 2σ(<i>I</i>)</td></tr><tr><td>Radiation source: fine-focus sealed tube</td><td><i>R</i><sub>int</sub> = 0.054</td></tr><tr><td>φ and ω scans</td><td>θ<sub>max</sub> = 27.5°, θ<sub>min</sub> = 2.2°</td></tr><tr><td>Absorption correction: multi-scan<br>(SADABS; Bruker, 2016)</td><td><i>h</i> = −10→11<br><i>k</i> = −17→24<br><i>l</i> = −14→14</td></tr><tr><td><i>T</i><sub>min</sub> = 0.677, <i>T</i><sub>max</sub> = 0.746<br>22287 measured reflections</td><td></td></tr></table>

### Refinement

<table><tr><td>Refinement on <i>F</i><sup>2</sup></td><td>1 restraint</td></tr><tr><td>Least-squares matrix: full</td><td>Primary atom site location: structure-invariant<br>direct methods</td></tr><tr><td><i>R</i>[<i>F</i><sup>2</sup> > 2σ(<i>F</i><sup>2</sup>)] = 0.060</td><td>Secondary atom site location: difference Fourier<br>map</td></tr><tr><td><i>wR</i>(<i>F</i><sup>2</sup>) = 0.188</td><td>Hydrogen site location: inferred from<br>neighbouring sites</td></tr><tr><td><i>S</i> = 1.04</td><td></td></tr><tr><td>4253 reflections</td><td></td></tr><tr><td>244 parameters</td><td></td></tr></table>
H-atom parameters constrained

$$w = 1/[\sigma^2(F_o^2) + (0.0761P)^2 + 0.7497P]$$

where $P = (F_o^2 + 2F_c^2)/3$

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

$$\Delta\rho_{\text{max}} = 0.38 \text{ e Å}^{-3}$$

$$\Delta\rho_{\text{min}} = -0.24 \text{ e Å}^{-3}$$

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></tr></thead><tbody><tr><td>O1</td><td>0.6364 (2)</td><td>0.24430 (9)</td><td>0.60030 (16)</td><td>0.0668 (5)</td></tr><tr><td>O2</td><td>0.6604 (2)</td><td>0.34222 (11)</td><td>0.77924 (17)</td><td>0.0787 (6)</td></tr><tr><td>C1</td><td>0.3801 (2)</td><td>0.42320 (11)</td><td>0.5380 (2)</td><td>0.0453 (5)</td></tr><tr><td>C2</td><td>0.2840 (3)</td><td>0.48294 (13)</td><td>0.5167 (2)</td><td>0.0565 (6)</td></tr><tr><td>H2</td><td>0.290850</td><td>0.516663</td><td>0.578499</td><td>0.068*</td></tr><tr><td>C3</td><td>0.1779 (3)</td><td>0.49239 (14)</td><td>0.4035 (3)</td><td>0.0606 (7)</td></tr><tr><td>C4</td><td>0.1685 (3)</td><td>0.44202 (16)</td><td>0.3149 (3)</td><td>0.0665 (7)</td></tr><tr><td>H4</td><td>0.096780</td><td>0.447513</td><td>0.240048</td><td>0.080*</td></tr><tr><td>C5</td><td>0.2611 (3)</td><td>0.38383 (14)</td><td>0.3329 (2)</td><td>0.0605 (7)</td></tr><tr><td>H5</td><td>0.253041</td><td>0.350819</td><td>0.269920</td><td>0.073*</td></tr><tr><td>C6</td><td>0.3690 (2)</td><td>0.37294 (12)</td><td>0.4457 (2)</td><td>0.0463 (5)</td></tr><tr><td>C7</td><td>0.0744 (4)</td><td>0.55686 (17)</td><td>0.3816 (3)</td><td>0.0857 (9)</td></tr><tr><td>H7A</td><td>0.097017</td><td>0.586438</td><td>0.453541</td><td>0.129*</td></tr><tr><td>H7B</td><td>0.090205</td><td>0.583627</td><td>0.313222</td><td>0.129*</td></tr><tr><td>H7C</td><td>-0.029766</td><td>0.541485</td><td>0.364004</td><td>0.129*</td></tr><tr><td>N1</td><td>0.4634 (2)</td><td>0.31227 (10)</td><td>0.46724 (17)</td><td>0.0479 (5)</td></tr><tr><td>C8</td><td>0.5589 (3)</td><td>0.29843 (12)</td><td>0.5791 (2)</td><td>0.0502 (6)</td></tr><tr><td>C9</td><td>0.5729 (3)</td><td>0.35335 (13)</td><td>0.6795 (2)</td><td>0.0530 (6)</td></tr><tr><td>N2</td><td>0.4870 (2)</td><td>0.41352 (10)</td><td>0.65252 (17)</td><td>0.0477 (5)</td></tr><tr><td>C10</td><td>0.4593 (3)</td><td>0.25871 (12)</td><td>0.3703 (2)</td><td>0.0564 (6)</td></tr><tr><td>H10A</td><td>0.356426</td><td>0.255943</td><td>0.318086</td><td>0.068*</td></tr><tr><td>H10B</td><td>0.484757</td><td>0.212320</td><td>0.408395</td><td>0.068*</td></tr><tr><td>C11</td><td>0.5669 (3)</td><td>0.27494 (12)</td><td>0.2918 (2)</td><td>0.0520 (6)</td></tr><tr><td>C12</td><td>0.7141 (3)</td><td>0.29739 (15)</td><td>0.3413 (3)</td><td>0.0682 (7)</td></tr><tr><td>H12</td><td>0.746539</td><td>0.306858</td><td>0.424992</td><td>0.082*</td></tr><tr><td>C13</td><td>0.8143 (4)</td><td>0.30607 (17)</td><td>0.2690 (3)</td><td>0.0839 (10)</td></tr><tr><td>H13</td><td>0.913384</td><td>0.321355</td><td>0.303781</td><td>0.101*</td></tr><tr><td>C14</td><td>0.7672 (5)</td><td>0.29203 (17)</td><td>0.1452 (4)</td><td>0.0907 (11)</td></tr><tr><td>H14</td><td>0.834725</td><td>0.297218</td><td>0.096117</td><td>0.109*</td></tr><tr><td>C15</td><td>0.6232 (6)</td><td>0.2708 (2)</td><td>0.0954 (3)</td><td>0.1045 (12)</td></tr><tr><td>H15</td><td>0.590820</td><td>0.262012</td><td>0.011500</td><td>0.125*</td></tr><tr><td>C16</td><td>0.5229 (4)</td><td>0.26191 (17)</td><td>0.1682 (3)</td><td>0.0820 (9)</td></tr><tr><td>H16</td><td>0.423893</td><td>0.246823</td><td>0.132573</td><td>0.098*</td></tr><tr><td>C23</td><td>0.5078 (3)</td><td>0.46790 (13)</td><td>0.7488 (2)</td><td>0.0561 (6)</td></tr><tr><td>H23A</td><td>0.502294</td><td>0.514721</td><td>0.711069</td><td>0.067*</td></tr><tr><td>H23B</td><td>0.608828</td><td>0.462678</td><td>0.803360</td><td>0.067*</td></tr></tbody></table>
<table><tr><td>C24</td><td>0.3920 (3)</td><td>0.46424 (11)</td><td>0.8239 (2)</td><td>0.0486 (5)</td></tr><tr><td>C25</td><td>0.3412 (3)</td><td>0.52590 (13)</td><td>0.8661 (2)</td><td>0.0641 (7)</td></tr><tr><td>H25</td><td>0.373901</td><td>0.569841</td><td>0.844097</td><td>0.077*</td></tr><tr><td>C26</td><td>0.2429 (4)</td><td>0.52371 (16)</td><td>0.9403 (3)</td><td>0.0785 (9)</td></tr><tr><td>H26</td><td>0.208237</td><td>0.565956</td><td>0.967137</td><td>0.094*</td></tr><tr><td>C27</td><td>0.1958 (4)</td><td>0.45942 (18)</td><td>0.9747 (3)</td><td>0.0799 (9)</td></tr><tr><td>H27</td><td>0.129675</td><td>0.457886</td><td>1.025374</td><td>0.096*</td></tr><tr><td>C28</td><td>0.2455 (4)</td><td>0.39791 (16)</td><td>0.9349 (3)</td><td>0.0777 (8)</td></tr><tr><td>H28</td><td>0.214200</td><td>0.354182</td><td>0.959034</td><td>0.093*</td></tr><tr><td>C29</td><td>0.3424 (3)</td><td>0.39995 (13)</td><td>0.8588 (3)</td><td>0.0666 (7)</td></tr><tr><td>H29</td><td>0.374561</td><td>0.357497</td><td>0.830698</td><td>0.080*</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>O1</td><td>0.0702 (12)</td><td>0.0659 (11)</td><td>0.0686 (12)</td><td>0.0218 (9)</td><td>0.0256 (9)</td><td>0.0050 (8)</td></tr><tr><td>O2</td><td>0.0710 (13)</td><td>0.1036 (15)</td><td>0.0554 (11)</td><td>0.0349 (11)</td><td>0.0050 (10)</td><td>-0.0041 (10)</td></tr><tr><td>C1</td><td>0.0359 (11)</td><td>0.0508 (12)</td><td>0.0539 (14)</td><td>0.0000 (9)</td><td>0.0197 (10)</td><td>0.0130 (10)</td></tr><tr><td>C2</td><td>0.0536 (14)</td><td>0.0563 (13)</td><td>0.0671 (16)</td><td>0.0013 (11)</td><td>0.0292 (13)</td><td>0.0090 (12)</td></tr><tr><td>C3</td><td>0.0433 (13)</td><td>0.0678 (15)</td><td>0.0736 (18)</td><td>0.0060 (11)</td><td>0.0204 (13)</td><td>0.0259 (14)</td></tr><tr><td>C4</td><td>0.0497 (15)</td><td>0.089 (2)</td><td>0.0604 (16)</td><td>0.0034 (14)</td><td>0.0131 (12)</td><td>0.0162 (15)</td></tr><tr><td>C5</td><td>0.0476 (14)</td><td>0.0820 (17)</td><td>0.0528 (15)</td><td>-0.0043 (13)</td><td>0.0149 (12)</td><td>0.0033 (13)</td></tr><tr><td>C6</td><td>0.0370 (11)</td><td>0.0550 (12)</td><td>0.0514 (13)</td><td>-0.0041 (10)</td><td>0.0197 (10)</td><td>0.0057 (10)</td></tr><tr><td>C7</td><td>0.071 (2)</td><td>0.090 (2)</td><td>0.094 (2)</td><td>0.0186 (17)</td><td>0.0178 (17)</td><td>0.0233 (18)</td></tr><tr><td>N1</td><td>0.0414 (10)</td><td>0.0542 (11)</td><td>0.0525 (12)</td><td>-0.0031 (8)</td><td>0.0200 (9)</td><td>0.0006 (9)</td></tr><tr><td>C8</td><td>0.0458 (13)</td><td>0.0563 (13)</td><td>0.0540 (14)</td><td>0.0056 (11)</td><td>0.0231 (11)</td><td>0.0057 (11)</td></tr><tr><td>C9</td><td>0.0449 (13)</td><td>0.0656 (15)</td><td>0.0518 (14)</td><td>0.0104 (11)</td><td>0.0184 (12)</td><td>0.0029 (11)</td></tr><tr><td>N2</td><td>0.0442 (10)</td><td>0.0510 (10)</td><td>0.0519 (11)</td><td>0.0002 (8)</td><td>0.0194 (9)</td><td>-0.0012 (8)</td></tr><tr><td>C10</td><td>0.0487 (14)</td><td>0.0588 (14)</td><td>0.0650 (16)</td><td>-0.0127 (11)</td><td>0.0204 (12)</td><td>-0.0112 (12)</td></tr><tr><td>C11</td><td>0.0514 (14)</td><td>0.0517 (12)</td><td>0.0570 (14)</td><td>0.0012 (11)</td><td>0.0213 (11)</td><td>-0.0011 (11)</td></tr><tr><td>C12</td><td>0.0526 (15)</td><td>0.0883 (19)</td><td>0.0666 (17)</td><td>-0.0084 (14)</td><td>0.0205 (13)</td><td>0.0175 (14)</td></tr><tr><td>C13</td><td>0.0586 (17)</td><td>0.087 (2)</td><td>0.117 (3)</td><td>0.0116 (15)</td><td>0.0420 (18)</td><td>0.0379 (19)</td></tr><tr><td>C14</td><td>0.116 (3)</td><td>0.0689 (18)</td><td>0.117 (3)</td><td>0.0319 (19)</td><td>0.084 (3)</td><td>0.0182 (18)</td></tr><tr><td>C15</td><td>0.143 (4)</td><td>0.109 (3)</td><td>0.082 (2)</td><td>-0.003 (3)</td><td>0.066 (3)</td><td>-0.024 (2)</td></tr><tr><td>C16</td><td>0.087 (2)</td><td>0.094 (2)</td><td>0.0682 (19)</td><td>-0.0083 (17)</td><td>0.0272 (16)</td><td>-0.0236 (16)</td></tr><tr><td>C23</td><td>0.0534 (14)</td><td>0.0531 (13)</td><td>0.0644 (15)</td><td>-0.0076 (11)</td><td>0.0198 (12)</td><td>-0.0054 (11)</td></tr><tr><td>C24</td><td>0.0478 (13)</td><td>0.0474 (12)</td><td>0.0513 (13)</td><td>-0.0012 (10)</td><td>0.0142 (10)</td><td>-0.0025 (10)</td></tr><tr><td>C25</td><td>0.0786 (19)</td><td>0.0498 (13)</td><td>0.0684 (17)</td><td>0.0069 (12)</td><td>0.0272 (15)</td><td>-0.0007 (12)</td></tr><tr><td>C26</td><td>0.099 (2)</td><td>0.0731 (18)</td><td>0.0750 (19)</td><td>0.0230 (17)</td><td>0.0426 (17)</td><td>-0.0042 (15)</td></tr><tr><td>C27</td><td>0.082 (2)</td><td>0.106 (2)</td><td>0.0638 (18)</td><td>0.0093 (18)</td><td>0.0411 (16)</td><td>0.0004 (17)</td></tr><tr><td>C28</td><td>0.090 (2)</td><td>0.0710 (18)</td><td>0.085 (2)</td><td>-0.0113 (16)</td><td>0.0457 (17)</td><td>0.0041 (15)</td></tr><tr><td>C29</td><td>0.0773 (18)</td><td>0.0492 (13)</td><td>0.0837 (19)</td><td>-0.0066 (12)</td><td>0.0396 (15)</td><td>-0.0059 (13)</td></tr></tbody></table>

Geometric parameters (Å, °)

<table><tr><td>O1—C8</td><td>1.222 (3)</td><td>C16—H16</td><td>0.9300</td></tr><tr><td>O2—C9</td><td>1.217 (3)</td><td>C15—C14</td><td>1.345 (5)</td></tr><tr><td>C1—C6</td><td>1.388 (3)</td><td>C15—H15</td><td>0.9300</td></tr></table>
<table><tr><td>C1—C2</td><td>1.401 (3)</td></tr><tr><td>C1—N2</td><td>1.414 (3)</td></tr><tr><td>C2—C3</td><td>1.400 (4)</td></tr><tr><td>C2—H2</td><td>0.9300</td></tr><tr><td>C3—C4</td><td>1.360 (4)</td></tr><tr><td>C3—C7</td><td>1.511 (4)</td></tr><tr><td>C4—C5</td><td>1.360 (4)</td></tr><tr><td>C4—H4</td><td>0.9300</td></tr><tr><td>C5—C6</td><td>1.407 (3)</td></tr><tr><td>C5—H5</td><td>0.9300</td></tr><tr><td>C6—N1</td><td>1.406 (3)</td></tr><tr><td>N1—C8</td><td>1.359 (3)</td></tr><tr><td>N1—C10</td><td>1.476 (3)</td></tr><tr><td>C8—C9</td><td>1.510 (3)</td></tr><tr><td>C9—N2</td><td>1.360 (3)</td></tr><tr><td>N2—C23</td><td>1.464 (3)</td></tr><tr><td>C10—C11</td><td>1.507 (3)</td></tr><tr><td>C10—H10A</td><td>0.9700</td></tr><tr><td>C10—H10B</td><td>0.9700</td></tr><tr><td>C11—C16</td><td>1.370 (4)</td></tr><tr><td>C11—C12</td><td>1.376 (4)</td></tr><tr><td>C16—C15</td><td>1.384 (5)</td></tr></table>

<table><tr><td>C6—C1—C2</td><td>119.4 (2)</td></tr><tr><td>C6—C1—N2</td><td>119.92 (19)</td></tr><tr><td>C2—C1—N2</td><td>120.7 (2)</td></tr><tr><td>C3—C2—C1</td><td>120.7 (2)</td></tr><tr><td>C3—C2—H2</td><td>119.7</td></tr><tr><td>C1—C2—H2</td><td>119.7</td></tr><tr><td>C4—C3—C2</td><td>118.7 (2)</td></tr><tr><td>C4—C3—C7</td><td>121.0 (3)</td></tr><tr><td>C2—C3—C7</td><td>120.3 (3)</td></tr><tr><td>C5—C4—C3</td><td>121.7 (3)</td></tr><tr><td>C5—C4—H4</td><td>119.1</td></tr><tr><td>C3—C4—H4</td><td>119.1</td></tr><tr><td>C4—C5—C6</td><td>120.8 (3)</td></tr><tr><td>C4—C5—H5</td><td>119.6</td></tr><tr><td>C6—C5—H5</td><td>119.6</td></tr><tr><td>C1—C6—N1</td><td>119.6 (2)</td></tr><tr><td>C1—C6—C5</td><td>118.6 (2)</td></tr><tr><td>N1—C6—C5</td><td>121.7 (2)</td></tr><tr><td>C8—N1—C6</td><td>122.01 (19)</td></tr><tr><td>C8—N1—C10</td><td>116.47 (19)</td></tr><tr><td>C6—N1—C10</td><td>121.47 (19)</td></tr><tr><td>O1—C8—N1</td><td>122.6 (2)</td></tr><tr><td>O1—C8—C9</td><td>118.9 (2)</td></tr><tr><td>N1—C8—C9</td><td>118.5 (2)</td></tr><tr><td>O2—C9—N2</td><td>123.4 (2)</td></tr></table>

<table><tr><td>C14—C13</td><td>1.376 (5)</td></tr><tr><td>C14—H14</td><td>0.9300</td></tr><tr><td>C13—C12</td><td>1.378 (4)</td></tr><tr><td>C13—H13</td><td>0.9300</td></tr><tr><td>C12—H12</td><td>0.9300</td></tr><tr><td>C23—C24</td><td>1.511 (3)</td></tr><tr><td>C23—H23A</td><td>0.9700</td></tr><tr><td>C23—H23B</td><td>0.9700</td></tr><tr><td>C24—C25</td><td>1.373 (3)</td></tr><tr><td>C24—C29</td><td>1.378 (3)</td></tr><tr><td>C29—C28</td><td>1.378 (4)</td></tr><tr><td>C29—H29</td><td>0.9300</td></tr><tr><td>C28—C27</td><td>1.355 (4)</td></tr><tr><td>C28—H28</td><td>0.9300</td></tr><tr><td>C27—C26</td><td>1.366 (4)</td></tr><tr><td>C27—H27</td><td>0.9300</td></tr><tr><td>C26—C25</td><td>1.371 (4)</td></tr><tr><td>C26—H26</td><td>0.9300</td></tr><tr><td>C25—H25</td><td>0.9300</td></tr><tr><td>C7—H7A</td><td>0.9600</td></tr><tr><td>C7—H7B</td><td>0.9600</td></tr><tr><td>C7—H7C</td><td>0.9600</td></tr></table>

<table><tr><td>C14—C15—C16</td><td>120.4 (3)</td></tr><tr><td>C14—C15—H15</td><td>119.8</td></tr><tr><td>C16—C15—H15</td><td>119.8</td></tr><tr><td>C15—C14—C13</td><td>119.7 (3)</td></tr><tr><td>C15—C14—H14</td><td>120.1</td></tr><tr><td>C13—C14—H14</td><td>120.1</td></tr><tr><td>C14—C13—C12</td><td>119.8 (3)</td></tr><tr><td>C14—C13—H13</td><td>120.1</td></tr><tr><td>C12—C13—H13</td><td>120.1</td></tr><tr><td>C11—C12—C13</td><td>121.1 (3)</td></tr><tr><td>C11—C12—H12</td><td>119.4</td></tr><tr><td>C13—C12—H12</td><td>119.4</td></tr><tr><td>N2—C23—C24</td><td>114.05 (18)</td></tr><tr><td>N2—C23—H23A</td><td>108.7</td></tr><tr><td>C24—C23—H23A</td><td>108.7</td></tr><tr><td>N2—C23—H23B</td><td>108.7</td></tr><tr><td>C24—C23—H23B</td><td>108.7</td></tr><tr><td>H23A—C23—H23B</td><td>107.6</td></tr><tr><td>C25—C24—C29</td><td>118.2 (2)</td></tr><tr><td>C25—C24—C23</td><td>120.0 (2)</td></tr><tr><td>C29—C24—C23</td><td>121.7 (2)</td></tr><tr><td>C28—C29—C24</td><td>120.7 (2)</td></tr><tr><td>C28—C29—H29</td><td>119.7</td></tr><tr><td>C24—C29—H29</td><td>119.7</td></tr><tr><td>C27—C28—C29</td><td>120.2 (3)</td></tr></table>
<table><tr><td>O2—C9—C8</td><td>119.1 (2)</td></tr><tr><td>N2—C9—C8</td><td>117.6 (2)</td></tr><tr><td>C9—N2—C1</td><td>122.08 (19)</td></tr><tr><td>C9—N2—C23</td><td>116.9 (2)</td></tr><tr><td>C1—N2—C23</td><td>121.01 (19)</td></tr><tr><td>N1—C10—C11</td><td>113.57 (18)</td></tr><tr><td>N1—C10—H10A</td><td>108.9</td></tr><tr><td>C11—C10—H10A</td><td>108.9</td></tr><tr><td>N1—C10—H10B</td><td>108.9</td></tr><tr><td>C11—C10—H10B</td><td>108.9</td></tr><tr><td>H10A—C10—H10B</td><td>107.7</td></tr><tr><td>C16—C11—C12</td><td>117.8 (2)</td></tr><tr><td>C16—C11—C10</td><td>119.8 (2)</td></tr><tr><td>C12—C11—C10</td><td>122.2 (2)</td></tr><tr><td>C11—C16—C15</td><td>121.2 (3)</td></tr><tr><td>C11—C16—H16</td><td>119.4</td></tr><tr><td>C15—C16—H16</td><td>119.4</td></tr></table>

<table><tr><td>C6—C1—C2—C3</td><td>-0.2 (3)</td></tr><tr><td>N2—C1—C2—C3</td><td>-179.82 (19)</td></tr><tr><td>C1—C2—C3—C4</td><td>0.8 (3)</td></tr><tr><td>C1—C2—C3—C7</td><td>179.8 (2)</td></tr><tr><td>C2—C3—C4—C5</td><td>-1.3 (4)</td></tr><tr><td>C7—C3—C4—C5</td><td>179.7 (2)</td></tr><tr><td>C3—C4—C5—C6</td><td>1.2 (4)</td></tr><tr><td>C2—C1—C6—N1</td><td>-178.95 (18)</td></tr><tr><td>N2—C1—C6—N1</td><td>0.6 (3)</td></tr><tr><td>C2—C1—C6—C5</td><td>0.1 (3)</td></tr><tr><td>N2—C1—C6—C5</td><td>179.71 (18)</td></tr><tr><td>C4—C5—C6—C1</td><td>-0.6 (3)</td></tr><tr><td>C4—C5—C6—N1</td><td>178.5 (2)</td></tr><tr><td>C1—C6—N1—C8</td><td>4.6 (3)</td></tr><tr><td>C5—C6—N1—C8</td><td>-174.4 (2)</td></tr><tr><td>C1—C6—N1—C10</td><td>-177.85 (18)</td></tr><tr><td>C5—C6—N1—C10</td><td>3.1 (3)</td></tr><tr><td>C6—N1—C8—O1</td><td>176.7 (2)</td></tr><tr><td>C10—N1—C8—O1</td><td>-1.0 (3)</td></tr><tr><td>C6—N1—C8—C9</td><td>-5.3 (3)</td></tr><tr><td>C10—N1—C8—C9</td><td>177.02 (19)</td></tr><tr><td>O1—C8—C9—O2</td><td>-0.4 (3)</td></tr><tr><td>N1—C8—C9—O2</td><td>-178.5 (2)</td></tr><tr><td>O1—C8—C9—N2</td><td>179.0 (2)</td></tr><tr><td>N1—C8—C9—N2</td><td>0.9 (3)</td></tr><tr><td>O2—C9—N2—C1</td><td>-176.4 (2)</td></tr><tr><td>C8—C9—N2—C1</td><td>4.2 (3)</td></tr><tr><td>O2—C9—N2—C23</td><td>2.4 (3)</td></tr><tr><td>C8—C9—N2—C23</td><td>-176.91 (19)</td></tr></table>

<table><tr><td>C27—C28—H28</td><td>119.9</td></tr><tr><td>C29—C28—H28</td><td>119.9</td></tr><tr><td>C28—C27—C26</td><td>120.0 (3)</td></tr><tr><td>C28—C27—H27</td><td>120.0</td></tr><tr><td>C26—C27—H27</td><td>120.0</td></tr><tr><td>C27—C26—C25</td><td>119.9 (2)</td></tr><tr><td>C27—C26—H26</td><td>120.0</td></tr><tr><td>C25—C26—H26</td><td>120.0</td></tr><tr><td>C26—C25—C24</td><td>121.0 (2)</td></tr><tr><td>C26—C25—H25</td><td>119.5</td></tr><tr><td>C24—C25—H25</td><td>119.5</td></tr><tr><td>C3—C7—H7A</td><td>109.5</td></tr><tr><td>C3—C7—H7B</td><td>109.5</td></tr><tr><td>H7A—C7—H7B</td><td>109.5</td></tr><tr><td>C3—C7—H7C</td><td>109.5</td></tr><tr><td>H7A—C7—H7C</td><td>109.5</td></tr><tr><td>H7B—C7—H7C</td><td>109.5</td></tr></table>

<table><tr><td>C6—C1—N2—C9</td><td>-5.1 (3)</td></tr><tr><td>C2—C1—N2—C9</td><td>174.47 (19)</td></tr><tr><td>C6—C1—N2—C23</td><td>176.09 (18)</td></tr><tr><td>C2—C1—N2—C23</td><td>-4.3 (3)</td></tr><tr><td>C8—N1—C10—C11</td><td>-93.4 (2)</td></tr><tr><td>C6—N1—C10—C11</td><td>88.9 (2)</td></tr><tr><td>N1—C10—C11—C16</td><td>-141.3 (2)</td></tr><tr><td>N1—C10—C11—C12</td><td>44.0 (3)</td></tr><tr><td>C12—C11—C16—C15</td><td>0.2 (4)</td></tr><tr><td>C10—C11—C16—C15</td><td>-174.7 (3)</td></tr><tr><td>C11—C16—C15—C14</td><td>0.5 (5)</td></tr><tr><td>C16—C15—C14—C13</td><td>-1.0 (5)</td></tr><tr><td>C15—C14—C13—C12</td><td>0.8 (5)</td></tr><tr><td>C16—C11—C12—C13</td><td>-0.4 (4)</td></tr><tr><td>C10—C11—C12—C13</td><td>174.4 (2)</td></tr><tr><td>C14—C13—C12—C11</td><td>-0.1 (4)</td></tr><tr><td>C9—N2—C23—C24</td><td>-96.7 (2)</td></tr><tr><td>C1—N2—C23—C24</td><td>82.2 (2)</td></tr><tr><td>N2—C23—C24—C25</td><td>-144.8 (2)</td></tr><tr><td>N2—C23—C24—C29</td><td>39.5 (3)</td></tr><tr><td>C25—C24—C29—C28</td><td>-0.6 (4)</td></tr><tr><td>C23—C24—C29—C28</td><td>175.1 (3)</td></tr><tr><td>C24—C29—C28—C27</td><td>1.2 (5)</td></tr><tr><td>C29—C28—C27—C26</td><td>-0.6 (5)</td></tr><tr><td>C28—C27—C26—C25</td><td>-0.4 (5)</td></tr><tr><td>C27—C26—C25—C24</td><td>1.0 (5)</td></tr><tr><td>C29—C24—C25—C26</td><td>-0.4 (4)</td></tr><tr><td>C23—C24—C25—C26</td><td>-176.2 (3)</td></tr></table>
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C11–C16 benzene ring.

<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>C10—H10A···O2<sup>i</sup></td><td>0.97</td><td>2.52</td><td>3.251 (3)</td><td>132</td></tr><tr><td>C16—H16···O1<sup>i</sup></td><td>0.93</td><td>2.55</td><td>3.3984 (4)</td><td>152</td></tr><tr><td>C25—H25···Cg3<sup>ii</sup></td><td>0.93</td><td>2.83</td><td>3.683 (3)</td><td>153</td></tr></tbody></table>

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