Crystal structure of
3,5-bis(4-chlorophenyl)-1-propyl-1,3,5-triazacyclohexane

Leila Lefrada, Ahcene Bouchemma, Sofiane Bouacida, Nicolas Claiser,
Mohamed Souhassou

► To cite this version:

Leila Lefrada, Ahcene Bouchemma, Sofiane Bouacida, Nicolas Claiser, Mohamed Souhassou. Crystal structure of 3,5-bis(4-chlorophenyl)-1-propyl-1,3,5-triazacyclohexane. Acta Crystallographica Section E: Structure Reports Online [2001-2014], 2014, 70 (9), pp.o1061 - o1062. 10.1107/S1600536814019060. hal-01521985

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<figure><img src="image_1.png" /></figure>

Distributed under a Creative Commons Attribution 4.0 International License
Crystal structure of
3,5-bis(4-chlorophenyl)-1-propyl-1,3,5-triazacyclohexane

Leila Lefrada, Ahcene Bouchemma, Sofiane Bouacida, Nicolas Claiser,
Mohamed Souhassou

► To cite this version:

Leila Lefrada, Ahcene Bouchemma, Sofiane Bouacida, Nicolas Claiser, Mohamed Souhas-bou. Crystal structure of 3,5-bis(4-chlorophenyl)-1-propyl-1,3,5-triazacyclohexane. Acta Crystallographica Section E: Structure Reports Online [2001-2014], 2014, 70 (9), pp.o1061 - o1062. 10.1107/S1600536814019060. hal-01521985

HAL Id: hal-01521985

https://hal.univ-lorraine.fr/hal-01521985v1

Submitted on 18 Jan 2024

**HAL** is a multi-disciplinary open access
archive for the deposit and dissemination of sci-
entific research documents, whether they are pub-
lished or not. The documents may come from
teaching and research institutions in France or
abroad, or from public or private research centers.

L'archive ouverte pluridisciplinaire HAL, est
destinée au dépôt et à la diffusion de documents
scientifiques de niveau recherche, publiés ou non,
émanant des établissements d'enseignement et de
recherche français ou étrangers, des laboratoires
publics ou privés.

<figure><img src="image_1.png" /></figure>

Distributed under a Creative Commons Attribution 4.0 International License
# Crystal structure of 3,5-bis(4-chlorophenyl)-1-propyl-1,3,5-triazacyclohexane

Leila Lefrada,ª,ᵇ Ahcene Bouchemma,ª,ᵇ Sofiane Bouacida,ᶜ,ᵇ* Nicolas Claiserᵈ and Mohamed Souhassouᵈ

ªLaboratoire de chimie appliquée et technologie des matériaux, LCATM, Université Oum El Bouaghi, Algeria, ᵇDépartement Sciences de la matière, Faculté des sciences exactes et sciences de la nature et de la vie, Université Oum El Bouaghi, Algeria, ᶜUnité de recherche de CHimie de l'environnement et Moléculaire Structurale, CHEMS, Faculté des sciences exactes, Université Constantine 1, Algeria, and ᵈLaboratoire de Cristallographie, Résonance Magnétique et Modélisations, UMR 7036 CNRS, Institut Jean Barriol, Université de Lorraine, Nancy, France.

*Correspondence e-mail: bouacida_sofiane@yahoo.fr

Received 25 July 2014; accepted 22 August 2014

Edited by A. J. Lough, University of Toronto, Canada

In the title molecule, C₁₈H₂₁Cl₂N₃, the triazacyclohexane ring adopts a chair conformation with both 4-chlorophenyl substituents in axial positions and the propyl group in an equatorial site. The dihedral angle between the planes of the benzene rings is 49.5 (1)°. In the crystal, molecules are arranged in a head-to-tail fashion, forming columns along [010], and pairs of weak C—H···π interactions form inversion dimers between columns.

**Keywords:** crystal structure; triazacyclohexane; C—H···π interactions.

CCDC reference: 1020727

## 1. Related literature

For conformations of 1,3,5-triaryl derivatives of 1,3,5-triazacyclohexane, see: Baker *et al.* (1978); Bouchemma *et al.* (1989, 1990); Bushweller (1995); Kleinpeter *et al.* (2005); Duke *et al.* (1973); Gilardi *et al.* (2003); Giumanini *et al.* (1985); Latreche *et al.* (2006); Mloston *et al.* (2006); Freeman *et al.* (2005); Wiberg *et al.* (1999).

<figure><img src="image_2.png" /></figure>

## 2. Experimental

### 2.1. Crystal data

<table><tr><td>C<sub>18</sub>H<sub>21</sub>Cl<sub>2</sub>N<sub>3</sub></td><td>γ = 99.055 (3)°</td></tr><tr><td>M<sub>r</sub> = 350.28</td><td>V = 893.19 (8) Å<sup>3</sup></td></tr><tr><td>Triclinic, <i>P</i>1</td><td>Z = 2</td></tr><tr><td><i>a</i> = 6.0785 (3) Å</td><td>Mo Kα radiation</td></tr><tr><td><i>b</i> = 10.3190 (6) Å</td><td>μ = 0.37 mm<sup>-1</sup></td></tr><tr><td><i>c</i> = 14.4360 (8) Å</td><td><i>T</i> = 295 K</td></tr><tr><td>α = 91.570 (3)°</td><td>0.22 × 0.13 × 0.07 mm</td></tr><tr><td>β = 91.946 (2)°</td><td></td></tr></table>

### 2.2. Data collection

<table><tr><td>Nonius KappaCCD diffractometer</td><td>13643 measured reflections</td></tr><tr><td>Absorption correction: multi-scan</td><td>3448 independent reflections</td></tr><tr><td>(Blessing, 1995)</td><td>2751 reflections with <i>I</i> > 2σ(<i>I</i>)</td></tr><tr><td><i>T</i><sub>min</sub> = 0.274, <i>T</i><sub>max</sub> = 0.467</td><td><i>R</i><sub>int</sub> = 0.016</td></tr></table>

### 2.3. Refinement

<table><caption>**Table 1**
Hydrogen-bond geometry (Å, °).</caption><tr><td><i>R</i>[<i>F</i><sup>2</sup> > 2σ(<i>F</i><sup>2</sup>)] = 0.049</td><td>209 parameters</td></tr><tr><td><i>wR</i>(<i>F</i><sup>2</sup>) = 0.142</td><td>H-atom parameters constrained</td></tr><tr><td><i>S</i> = 1.03</td><td>Δρ<sub>max</sub> = 0.45 e Å<sup>-3</sup></td></tr><tr><td>3448 reflections</td><td>Δρ<sub>min</sub> = -0.25 e Å<sup>-3</sup></td></tr></table>

Cg is centroid of C21–C26 ring.

<table><tr><td><i>D</i>—H···<i>A</i></td><td><i>D</i>—H</td><td>H···<i>A</i></td><td><i>D</i>···<i>A</i></td><td><i>D</i>—H···<i>A</i></td></tr><tr><td>C2—H2A···C<i>g</i><sup>i</sup></td><td>0.96</td><td>2.92</td><td>3.668 (3)</td><td>134</td></tr></table>

Symmetry code: (i) $-x, -y + 1, -z + 1$.

Data collection: **COLLECT** (Nonius, 1997); cell refinement: **SCALEPACK** (Otwinowski & Minor, 1997); data reduction: **DENZO** (Otwinowski & Minor, 1997) and **SCALEPACK**; program(s) used to solve structure: *SIR2002* (Burla *et al.*, 2005); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008); molecular graphics: **ORTEP-3 for Windows** (Farrugia, 2012) and
# Crystal structure of 3,5-bis(4-chlorophenyl)-1-propyl-1,3,5-triazacyclohexane

Leila Lefrada,ª,ᵇ Ahcene Bouchemma,ª,ᵇ Sofiane Bouacida,ᶜ,ᵇ* Nicolas Claiserᵈ and Mohamed Souhassouᵈ

ªLaboratoire de chimie appliquée et technologie des matériaux, LCATM, Université Oum El Bouaghi, Algeria, ᵇDépartement Sciences de la matière, Faculté des sciences exactes et sciences de la nature et de la vie, Université Oum El Bouaghi, Algeria, ᶜUnité de recherche de CHimie de l'environnement et Moléculaire Structurale, CHEMS, Faculté des sciences exactes, Université Constantine 1, Algeria, and ᵈLaboratoire de Cristallographie, Résonance Magnétique et Modélisations, UMR 7036 CNRS, Institut Jean Barriol, Université de Lorraine, Nancy, France.

*Correspondence e-mail: bouacida_sofiane@yahoo.fr

Received 25 July 2014; accepted 22 August 2014

Edited by A. J. Lough, University of Toronto, Canada

In the title molecule, C₁₈H₂₁Cl₂N₃, the triazacyclohexane ring adopts a chair conformation with both 4-chlorophenyl substituents in axial positions and the propyl group in an equatorial site. The dihedral angle between the planes of the benzene rings is 49.5 (1)°. In the crystal, molecules are arranged in a head-to-tail fashion, forming columns along [010], and pairs of weak C—H···π interactions form inversion dimers between columns.

**Keywords:** crystal structure; triazacyclohexane; C—H···π interactions.

CCDC reference: 1020727

## 1. Related literature

For conformations of 1,3,5-triaryl derivatives of 1,3,5-triazacyclohexane, see: Baker *et al.* (1978); Bouchemma *et al.* (1989, 1990); Bushweller (1995); Kleinpeter *et al.* (2005); Duke *et al.* (1973); Gilardi *et al.* (2003); Giumanini *et al.* (1985); Latreche *et al.* (2006); Mloston *et al.* (2006); Freeman *et al.* (2005); Wiberg *et al.* (1999).

<figure><img src="image_2.png" /></figure>

## 2. Experimental

### 2.1. Crystal data

$$C_{18}H_{21}Cl_2N_3$$

$$M_r = 350.28$$

$$Triclinic, \bar{P}1$$

$$a = 6.0785 (3) \AA$$

$$b = 10.3190 (6) \AA$$

$$c = 14.4360 (8) \AA$$

$$\alpha = 91.570 (3)^{\circ}$$

$$\beta = 91.946 (2)^{\circ}$$

$$\gamma = 99.055 (3)^{\circ}$$

$$V = 893.19 (8) \AA^3$$

$$Z = 2$$

$$Mo K\alpha radiation$$

$$\mu = 0.37 \text{ mm}^{-1}$$

$$T = 295 \text{ K}$$

$$0.22 \times 0.13 \times 0.07 \text{ mm}$$

### 2.2. Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan
(Blessing, 1995)
$$T_{\text{min}} = 0.274, T_{\text{max}} = 0.467$$

13643 measured reflections
3448 independent reflections
2751 reflections with *I* > 2σ(*I*)
$$R_{\text{int}} = 0.016$$

### 2.3. Refinement

$$R[F^2 > 2\sigma(F^2)] = 0.049$$

$$wR(F^2) = 0.142$$

$$S = 1.03$$

3448 reflections

209 parameters
H-atom parameters constrained
$\Delta\rho_{\text{max}} = 0.45 \text{ e } \AA^{-3}$
$\Delta\rho_{\text{min}} = -0.25 \text{ e } \AA^{-3}$

<caption>**Table 1**
Hydrogen-bond geometry (Å, °).</caption>

Cg is centroid of C21–C26 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>C2–H2A···Cg<sup>i</sup></td><td>0.96</td><td>2.92</td><td>3.668 (3)</td><td>134</td></tr></tbody></table>

Symmetry code: (i) $-x, -y + 1, -z + 1$.

Data collection: **COLLECT** (Nonius, 1997); cell refinement: **SCALEPACK** (Otwinowski & Minor, 1997); data reduction: **DENZO** (Otwinowski & Minor, 1997) and **SCALEPACK**; program(s) used to solve structure: *SIR2002* (Burla *et al.*, 2005); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008); molecular graphics: **ORTEP-3 for Windows** (Farrugia, 2012) and
DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: *WinGX* (Farrugia, 2012).

Acknowledgements

This work is supported by laboratory LCATM, Université Oum El Bouaghi, Algeria. Thanks are due to MESRS (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique, Algeria) for financial support.

Supporting information for this paper is available from the IUCr electronic archives (Reference: LH5723).

References

Baker, V. J., Ferguson, I. J., Katritzky, A. R., Patel, R. C. & Rahimi-Rastgoo, S. (1978). *J. Chem. Soc. Perkin Trans.* 2, pp. 377–381.

Blessing, R. H. (1995). *Acta Cryst.* **A51**, 33–38.

Bouchemma, A., McCabe, P. H. & Sim, G. A. (1989). *J. Chem. Soc. Perkin Trans.* 2, pp. 583–587.

Bouchemma, A., McCabe, P. H. & Sim, G. A. (1990). *Acta Cryst.* **C46**, 410–414.

Brandenburg, K. & Berndt, M. (2001). *DIAMOND*. Crystal Impact, Bonn, Germany.

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). *J. Appl. Cryst.* **38**, 381–388.

Bushweller, C. H. (1995). In *Conformational BehaVior of Six-Membered Rings. Analysis, Dynamics, and Stereoelectronic Effects*, edited by E. Juaristi. New York: VCH Publishers.

Duke, R. P., Jones, R. A. Y., Katritzky, A. R., Scattergood, R. & Riddell, F. G. (1973). *J. Chem. Soc. Perkin Trans.* 2, pp. 2109–2111.

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

Freeman, F., Asgari, N., Entezam, B., Gomarooni, F., Mac, J., Nguyen, M. H., Nguyen, N. N. T., Nguyen, T. P., Pham, N. B., Sultana, P., Welch, T. S. & Shainyan, B. A. (2005). *J. Quantum Chem.* **101**, 40–54.

Gilardi, R., Evans, R. N. & Duddu, R. (2003). *Acta Cryst.* **E59**, o1187–o1188.

Giumanini, A. G., Verardo, G., Randaccio, L., Bresciani-Pahor, N. & Traldi, P. (1985). *J. Prakt. Chem.* **327**, 739–748.

Kleinpeter, E., Koch, A. & Pihlaja, K. (2005). *Tetrahedron*, **61**, 7349–7358.

Latreche, S., Bouchemma, A., Bouacida, S., Bouhenguel, M. & Mousser, A. (2006). *Acta Cryst.* **E62**, o4674–o4675.

Mloston, G., Jasinski, M., Linden, A. & Heimgartner, H. (2006). *Helv. Chim. Acta*, **89**, 1304–1316.

Nonius (1997). *COLLECT*. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). *Methods in Enzymology*, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

Sheldrick, G. M. (2008). *Acta Cryst.* **A64**, 112–122.

Wiberg, K. B., Hammer, J. D., Castejon, H., Bailey, W. F., DeLeon, E. L. & Jarret, R. M. (1999). *J. Org. Chem.* **64**, 2085.
DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: *WinGX* (Farrugia, 2012).

## Acknowledgements

This work is supported by laboratory LCATM, Université Oum El Bouaghi, Algeria. Thanks are due to MESRS (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique, Algeria) for financial support.

Supporting information for this paper is available from the IUCr electronic archives (Reference: LH5723).

## References

Baker, V. J., Ferguson, I. J., Katritzky, A. R., Patel, R. C. & Rahimi-Rastgoo, S. (1978). *J. Chem. Soc. Perkin Trans.* 2, pp. 377–381.

Blessing, R. H. (1995). *Acta Cryst.* **A51**, 33–38.

Bouchemma, A., McCabe, P. H. & Sim, G. A. (1989). *J. Chem. Soc. Perkin Trans.* 2, pp. 583–587.

Bouchemma, A., McCabe, P. H. & Sim, G. A. (1990). *Acta Cryst.* **C46**, 410–414.

Brandenburg, K. & Berndt, M. (2001). *DIAMOND*. Crystal Impact, Bonn, Germany.

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). *J. Appl. Cryst.* **38**, 381–388.

Bushweller, C. H. (1995). In *Conformational BehaVior of Six-Membered Rings. Analysis, Dynamics, and Stereoelectronic Effects*, edited by E. Juaristi. New York: VCH Publishers.

Duke, R. P., Jones, R. A. Y., Katritzky, A. R., Scattergood, R. & Riddell, F. G. (1973). *J. Chem. Soc. Perkin Trans.* 2, pp. 2109–2111.

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

Freeman, F., Asgari, N., Entezam, B., Gomarooni, F., Mac, J., Nguyen, M. H., Nguyen, N. N. T., Nguyen, T. P., Pham, N. B., Sultana, P., Welch, T. S. & Shainyan, B. A. (2005). *J. Quantum Chem.* **101**, 40–54.

Gilardi, R., Evans, R. N. & Duddu, R. (2003). *Acta Cryst.* **E59**, o1187–o1188.

Giumanini, A. G., Verardo, G., Randaccio, L., Bresciani-Pahor, N. & Traldi, P. (1985). *J. Prakt. Chem.* **327**, 739–748.

Kleinpeter, E., Koch, A. & Pihlaja, K. (2005). *Tetrahedron*, **61**, 7349–7358.

Latreche, S., Bouchemma, A., Bouacida, S., Bouhenguel, M. & Mousser, A. (2006). *Acta Cryst.* **E62**, o4674–o4675.

Mloston, G., Jasinski, M., Linden, A. & Heimgartner, H. (2006). *Helv. Chim. Acta*, **89**, 1304–1316.

Nonius (1997). *COLLECT*. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). *Methods in Enzymology*, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

Sheldrick, G. M. (2008). *Acta Cryst.* **A64**, 112–122.

Wiberg, K. B., Hammer, J. D., Castejon, H., Bailey, W. F., DeLeon, E. L. & Jarret, R. M. (1999). *J. Org. Chem.* **64**, 2085.
supporting information

*Acta Cryst.* (2014). **E70**, o1061–o1062 [doi:10.1107/S1600536814019060]

# Crystal structure of 3,5-bis(4-chlorophenyl)-1-propyl-1,3,5-triazacyclohexane

Leila Lefrada, Ahcene Bouchamma, Sofiane Bouacida, Nicolas Claiser and Mohamed Souhassou

## S1. Comment

The conformational behaviour of substituted cyclohexanes as well as heterocyclohexanes has been the subject of numerous studies (Bushweller, 1995). The ring normally adopts the chair conformation unless specific intramolecular interactions stabilize the twist (Kleinpeter *et al.*, 2005) or boat conformers (Freeman *et al.*, 2005). Saturated six-membered rings are prevalent in organic chemistry. For cyclohexane, experimental and computational studies have established that the chair conformation is 5.5 kcal/mol more stable than the twist form (Wiberg *et al.*, 1999). N,N',N''-Trisubstituted 1,3,5-triazinanes are of interest as precursors for the preparation of different N-substituted imidazoles (Mloston *et al.*, 2006). The heterocyclic nucleus is expected to adopt a chair conformation and four distinct patterns of substituent orientation have to be considered, eee, eea, eaa and aaa, where e = equatorial and a = axial, with each of the conformers having axial repulsions involving the substituents or lone pairs of electrons on the N atoms. Several 1,3,5-tri-alkyl derivatives have been investigated in solution by dipole moment measurements and the results interpreted in terms of the eee conformer, the eea conformer (Baker *et al.*, 1978), and varying amounts of the eee, eea and eaa conformers (Duke *et al.*, 1973). Various 1,3,5-triaryl-1,3,5-triazacyclohexanes adopt the diaxial-equatorial orientation of substituents in the solid state thus avoiding 1,3-diaxial lone-pair repulsions (Giumanini *et al.* 1985; Gilardi *et al.* 2003 Bouchamma *et al.* 1989; 1990).

In the present work, a new derivate (I) of triazacyclohexane is reported and molecular structure is shown in Fig. 1. The 1,3,5-triazacycolohexane ring is in a chair conformation which is typical of this ring (Gilardi *et al.* 2003). The structure of a similar compound *viz* 1-propyl-3,5-bis-(4-fluorophenyl)-1,3,5-triazacycolohexane (II) has been reported (Latreche *et al.* 2006). In both (I) and (II) the heterocyclic rings adopt chair conformations with two fluorophenyl substituents situated in axial positions and a third group (propyl) equatorial. The dihedral angle between the benzene rings (C11-C16/C21-C26) is 49.5 (1)°. In the crystal, molecules are arranged in a 'head to tail' fashion forming columns along [010] (see Fig. 2) and pairs weak C—H···π interactions form inversion dimers between columns.

## S2. Experimental

The title compound was obtained by mixing a 2:1:1 stoichiometric ratio of propylamine and 4-chloroaniline with formalin in ethanol (25 ml) at 293K. The resulting solution was evaporated on a rotary evaporator to dryness and the white residue was recrystallized from cyclohexane.

## S3. Refinement

All non-H atoms were refined with anisotropic atomic displacement parameters. All H atoms were located in difference Fourier maps but introduced in calculated positions and treated as riding on their parent C atom, with C—H distances of 0.93 Å (C<sub>aromatic</sub>), 0.97 Å (C<sub>methylene</sub>) and 0.96 Å (C<sub>methyl</sub>) with U<sub>iso</sub>(H) = 1.2 U<sub>eq</sub>(C<sub>aromatic</sub> and C<sub>methylene</sub>) or 1.5 U<sub>eq</sub>(C<sub>methyl</sub>).
supporting information

*Acta Cryst.* (2014). **E70**, o1061–o1062 [doi:10.1107/S1600536814019060]

# Crystal structure of 3,5-bis(4-chlorophenyl)-1-propyl-1,3,5-triazacyclohexane

Leila Lefrada, Ahcene Bouchemma, Sofiane Bouacida, Nicolas Claiser and Mohamed Souhassou

## S1. Comment

The conformational behaviour of substituted cyclohexanes as well as heterocyclohexanes has been the subject of numerous studies (Bushweller, 1995). The ring normally adopts the chair conformation unless specific intramolecular interactions stabilize the twist (Kleinpeter *et al.*, 2005) or boat conformers (Freeman *et al.*, 2005). Saturated six-membered rings are prevalent in organic chemistry. For cyclohexane, experimental and computational studies have established that the chair conformation is 5.5 kcal/mol more stable than the twist form (Wiberg *et al.*, 1999). N,N',N''-Trisubstituted 1,3,5-triazinanes are of interest as precursors for the preparation of different N-substituted imidazoles (Mloston *et al.*, 2006). The heterocyclic nucleus is expected to adopt a chair conformation and four distinct patterns of substituent orientation have to be considered, eee, eea, eaa and aaa, where e = equatorial and a = axial, with each of the conformers having axial repulsions involving the substituents or lone pairs of electrons on the N atoms. Several 1,3,5-tri-alkyl derivatives have been investigated in solution by dipole moment measurements and the results interpreted in terms of the eee conformer, the eea conformer (Baker *et al.*, 1978), and varying amounts of the eee, eea and eaa conformers (Duke *et al.*, 1973). Various 1,3,5-triaryl-1,3,5-triazacyclohexanes adopt the diaxial-equatorial orientation of substituents in the solid state thus avoiding 1,3-diaxial lone-pair repulsions (Giumanini *et al.* 1985; Gilardi *et al.* 2003 Bouchemma *et al.* 1989; 1990).

In the present work, a new derivate (I) of triazacyclohexane is reported and molecular structure is shown in Fig. 1. The 1,3,5-triazacycolohexane ring is in a chair conformation which is typical of this ring (Gilardi *et al.* 2003). The structure of a similar compound *viz* 1-propyl-3,5-bis-(4-fluorophenyl)-1,3,5-triazacycolohexane (II) has been reported (Latreche *et al.* 2006). In both (I) and (II) the heterocyclic rings adopt chair conformations with two fluorophenyl substituents situated in axial positions and a third group (propyl) equatorial. The dihedral angle between the benzene rings (C11-C16/C21-C26) is 49.5 (1)°. In the crystal, molecules are arranged in a 'head to tail' fashion forming columns along [010] (see Fig. 2) and pairs weak C—H···π interactions form inversion dimers between columns.

## S2. Experimental

The title compound was obtained by mixing a 2:1:1 stoichiometric ratio of propylamine and 4-chloroaniline with formalin in ethanol (25 ml) at 293K. The resulting solution was evaporated on a rotary evaporator to dryness and the white residue was recrystallized from cyclohexane.

## S3. Refinement

All non-H atoms were refined with anisotropic atomic displacement parameters. All H atoms were located in difference Fourier maps but introduced in calculated positions and treated as riding on their parent C atom, with C—H distances of 0.93 Å (C<sub>aromatic</sub>), 0.97 Å (C<sub>methylene</sub>) and 0.96 Å (C<sub>methyl</sub>) with U<sub>iso</sub>(H) = 1.2 U<sub>eq</sub>(C<sub>aromatic</sub> and C<sub>methylene</sub>) or 1.5 U<sub>eq</sub>(C<sub>methyl</sub>).
<figure><img src="image_3.png" /><figcaption>Figure 1</figcaption></figure>

The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
<figure><img src="image_3.png" /><figcaption>Figure 1</figcaption></figure>

The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
<figure><img src="image_4.png" /><figcaption>**Figure 2**</figcaption></figure>

Part of the crystal structure of the title compound showing the 'head to tail' arrangement of molecules arranged in columns.

### 3,5-Bis(4-chlorophenyl)-1-propyl-1,3,5-triazacyclohexane

*Crystal data*

$C_{18}H_{21}Cl_2N_3$

$M_r = 350.28$

Triclinic, $P1$

Hall symbol: -P 1

$a = 6.0785 (3) Å$

$b = 10.3190 (6) Å$

$c = 14.4360 (8) Å$

$\alpha = 91.570 (3)^{\circ}$

$\beta = 91.946 (2)^{\circ}$

$\gamma = 99.055 (3)^{\circ}$

$V = 893.19 (8) Å^3$

$Z = 2$

$F(000) = 368$

$D_x = 1.302 \text{ Mg m}^{-3}$

Mo $K\alpha$ radiation, $\lambda = 0.71073$ Å

Cell parameters from 13346 reflections

$\theta = 1.5-27.3^{\circ}$

$\mu = 0.37 \text{ mm}^{-1}$

$T = 295$ K

Prism, colourless

$0.22 \times 0.13 \times 0.07$ mm
<figure><img src="image_4.png" /><figcaption>**Figure 2**</figcaption></figure>

Part of the crystal structure of the title compound showing the 'head to tail' arrangement of molecules arranged in columns.

**3,5-Bis(4-chlorophenyl)-1-propyl-1,3,5-triazacyclohexane**

*Crystal data*

$C_{18}H_{21}Cl_2N_3$

$M_r = 350.28$

Triclinic, $P1$

Hall symbol: -P 1

$a = 6.0785 (3) Å$

$b = 10.3190 (6) Å$

$c = 14.4360 (8) Å$

$\alpha = 91.570 (3)^{\circ}$

$\beta = 91.946 (2)^{\circ}$

$\gamma = 99.055 (3)^{\circ}$

$V = 893.19 (8) Å^3$

$Z = 2$

$F(000) = 368$

$D_x = 1.302 \text{ Mg m}^{-3}$

Mo $K\alpha$ radiation, $\lambda = 0.71073$ Å

Cell parameters from 13346 reflections

$\theta = 1.5-27.3^{\circ}$

$\mu = 0.37 \text{ mm}^{-1}$

$T = 295$ K

Prism, colourless

$0.22 \times 0.13 \times 0.07$ mm
## Data collection

Nonius KappaCCD 3448 independent reflections
diffractometer 2751 reflections with $I > 2\sigma(I)$

Graphite monochromator $R_{int} = 0.016$

$\omega$ and $\phi$ scans $\theta_{max} = 27.3^{\circ}$, $\theta_{min} = 1.4^{\circ}$

Absorption correction: multi-scan $h = -7 \rightarrow 7$

(Blessing, 1995) $k = -12 \rightarrow 12$

$T_{min} = 0.274$, $T_{max} = 0.467$ $l = -17 \rightarrow 17$

13643 measured reflections

## Refinement

Refinement on $F^2$ Secondary atom site location: difference Fourier
Least-squares matrix: full map

$R[F^2 > 2\sigma(F^2)] = 0.049$ Hydrogen site location: inferred from
$wR(F^2) = 0.142$ neighbouring sites

$S = 1.03$ H-atom parameters constrained

3448 reflections $w = 1/[\sigma^2(F_o^2) + (0.0652P)^2 + 0.413P]$

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

0 restraints $(\Delta/\sigma)_{max} < 0.001$
Primary atom site location: structure-invariant $\Delta\rho_{max} = 0.45$ e Å$^{-3}$

## Special details

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

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

## Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å$^2$)

<table><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>C1</td><td>-0.3001 (4)</td><td>0.4766 (3)</td><td>0.25020 (16)</td><td>0.0613 (6)</td></tr><tr><td>H1A</td><td>-0.3547</td><td>0.383</td><td>0.2459</td><td>0.074*</td></tr><tr><td>H1B</td><td>-0.4281</td><td>0.5221</td><td>0.2505</td><td>0.074*</td></tr><tr><td>C2</td><td>-0.0783 (4)</td><td>0.6456 (2)</td><td>0.34207 (17)</td><td>0.0633 (6)</td></tr><tr><td>H2A</td><td>0.0103</td><td>0.6653</td><td>0.3993</td><td>0.076*</td></tr><tr><td>H2B</td><td>-0.1997</td><td>0.6964</td><td>0.3432</td><td>0.076*</td></tr><tr><td>C3</td><td>-0.0772 (5)</td><td>0.6525 (2)</td><td>0.17830 (18)</td><td>0.0652 (6)</td></tr><tr><td>H3A</td><td>-0.1979</td><td>0.7039</td><td>0.1778</td><td>0.078*</td></tr><tr><td>H3B</td><td>0.013</td><td>0.6767</td><td>0.1254</td><td>0.078*</td></tr><tr><td>C4</td><td>0.1485 (6)</td><td>0.8253 (3)</td><td>0.2756 (2)</td><td>0.0847 (8)</td></tr><tr><td>H4A</td><td>0.0283</td><td>0.8751</td><td>0.2638</td><td>0.102*</td></tr><tr><td>H4B</td><td>0.2019</td><td>0.8438</td><td>0.3394</td><td>0.102*</td></tr><tr><td>C5</td><td>0.3281 (8)</td><td>0.8689 (4)</td><td>0.2147 (3)</td><td>0.1185 (14)</td></tr><tr><td>H5A</td><td>0.2688</td><td>0.865</td><td>0.1513</td><td>0.142*</td></tr><tr><td>H5B</td><td>0.4368</td><td>0.8096</td><td>0.2185</td><td>0.142*</td></tr><tr><td>C6</td><td>0.4450 (8)</td><td>1.0093 (4)</td><td>0.2390 (3)</td><td>0.1321 (17)</td></tr><tr><td>H6A</td><td>0.3366</td><td>1.0677</td><td>0.2395</td><td>0.198*</td></tr></tbody></table>
## Data collection

<table><tr><td>Nonius KappaCCD</td><td>3448 independent reflections</td></tr><tr><td>diffractometer</td><td>2751 reflections with I > 2σ(I)</td></tr><tr><td>Graphite monochromator</td><td>R<sub>int</sub> = 0.016</td></tr><tr><td>ω and φ scans</td><td>θ<sub>max</sub> = 27.3°, θ<sub>min</sub> = 1.4°</td></tr><tr><td>Absorption correction: multi-scan<br>(Blessing, 1995)</td><td>h = -7→7</td></tr><tr><td>T<sub>min</sub> = 0.274, T<sub>max</sub> = 0.467</td><td>k = -12→12</td></tr><tr><td>13643 measured reflections</td><td>l = -17→17</td></tr></table>

## Refinement

<table><tr><td>Refinement on F<sup>2</sup></td><td>Secondary atom site location: difference Fourier map</td></tr><tr><td>Least-squares matrix: full</td><td>Hydrogen site location: inferred from neighbouring sites</td></tr><tr><td>R[F<sup>2</sup> > 2σ(F<sup>2</sup>)] = 0.049</td><td>H-atom parameters constrained</td></tr><tr><td>wR(F<sup>2</sup>) = 0.142</td><td>w = 1/[σ<sup>2</sup>(F<sub>o</sub><sup>2</sup>) + (0.0652P)<sup>2</sup> + 0.413P]</td></tr><tr><td>S = 1.03</td><td>where P = (F<sub>o</sub><sup>2</sup> + 2F<sub>c</sub><sup>2</sup>)/3</td></tr><tr><td>3448 reflections</td><td>(Δ/σ)<sub>max</sub> < 0.001</td></tr><tr><td>209 parameters</td><td>Δρ<sub>max</sub> = 0.45 e Å<sup>-3</sup></td></tr><tr><td>0 restraints</td><td>Δρ<sub>min</sub> = -0.25 e Å<sup>-3</sup></td></tr><tr><td>Primary atom site location: structure-invariant<br>direct methods</td><td></td></tr></table>

## Special details

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

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

## Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

<table><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>C1</td><td>-0.3001 (4)</td><td>0.4766 (3)</td><td>0.25020 (16)</td><td>0.0613 (6)</td></tr><tr><td>H1A</td><td>-0.3547</td><td>0.383</td><td>0.2459</td><td>0.074*</td></tr><tr><td>H1B</td><td>-0.4281</td><td>0.5221</td><td>0.2505</td><td>0.074*</td></tr><tr><td>C2</td><td>-0.0783 (4)</td><td>0.6456 (2)</td><td>0.34207 (17)</td><td>0.0633 (6)</td></tr><tr><td>H2A</td><td>0.0103</td><td>0.6653</td><td>0.3993</td><td>0.076*</td></tr><tr><td>H2B</td><td>-0.1997</td><td>0.6964</td><td>0.3432</td><td>0.076*</td></tr><tr><td>C3</td><td>-0.0772 (5)</td><td>0.6525 (2)</td><td>0.17830 (18)</td><td>0.0652 (6)</td></tr><tr><td>H3A</td><td>-0.1979</td><td>0.7039</td><td>0.1778</td><td>0.078*</td></tr><tr><td>H3B</td><td>0.013</td><td>0.6767</td><td>0.1254</td><td>0.078*</td></tr><tr><td>C4</td><td>0.1485 (6)</td><td>0.8253 (3)</td><td>0.2756 (2)</td><td>0.0847 (8)</td></tr><tr><td>H4A</td><td>0.0283</td><td>0.8751</td><td>0.2638</td><td>0.102*</td></tr><tr><td>H4B</td><td>0.2019</td><td>0.8438</td><td>0.3394</td><td>0.102*</td></tr><tr><td>C5</td><td>0.3281 (8)</td><td>0.8689 (4)</td><td>0.2147 (3)</td><td>0.1185 (14)</td></tr><tr><td>H5A</td><td>0.2688</td><td>0.865</td><td>0.1513</td><td>0.142*</td></tr><tr><td>H5B</td><td>0.4368</td><td>0.8096</td><td>0.2185</td><td>0.142*</td></tr><tr><td>C6</td><td>0.4450 (8)</td><td>1.0093 (4)</td><td>0.2390 (3)</td><td>0.1321 (17)</td></tr><tr><td>H6A</td><td>0.3366</td><td>1.0677</td><td>0.2395</td><td>0.198*</td></tr></tbody></table>
<table><tr><td>H6B</td><td>0.5531</td><td>1.0364</td><td>0.1935</td><td>0.198*</td></tr><tr><td>H6C</td><td>0.5184</td><td>1.0117</td><td>0.2991</td><td>0.198*</td></tr><tr><td>C11</td><td>-0.0360 (4)</td><td>0.4255 (2)</td><td>0.13332 (14)</td><td>0.0505 (5)</td></tr><tr><td>C12</td><td>0.1801 (4)</td><td>0.4642 (2)</td><td>0.10651 (16)</td><td>0.0556 (5)</td></tr><tr><td>H12</td><td>0.2467</td><td>0.5511</td><td>0.1166</td><td>0.067*</td></tr><tr><td>C13</td><td>0.2992 (4)</td><td>0.3762 (2)</td><td>0.06492 (16)</td><td>0.0590 (6)</td></tr><tr><td>H13</td><td>0.4436</td><td>0.4041</td><td>0.0465</td><td>0.071*</td></tr><tr><td>C14</td><td>0.2027 (4)</td><td>0.2473 (2)</td><td>0.05101 (16)</td><td>0.0585 (6)</td></tr><tr><td>C15</td><td>-0.0100 (4)</td><td>0.2056 (2)</td><td>0.07759 (19)</td><td>0.0691 (7)</td></tr><tr><td>H15</td><td>-0.0742</td><td>0.1181</td><td>0.0685</td><td>0.083*</td></tr><tr><td>C16</td><td>-0.1281 (4)</td><td>0.2940 (2)</td><td>0.11776 (19)</td><td>0.0666 (6)</td></tr><tr><td>H16</td><td>-0.2732</td><td>0.2653</td><td>0.135</td><td>0.08*</td></tr><tr><td>C21</td><td>-0.0324 (4)</td><td>0.4175 (2)</td><td>0.36755 (14)</td><td>0.0491 (5)</td></tr><tr><td>C22</td><td>-0.1257 (4)</td><td>0.2865 (2)</td><td>0.37598 (18)</td><td>0.0622 (6)</td></tr><tr><td>H22</td><td>-0.2735</td><td>0.2589</td><td>0.3566</td><td>0.075*</td></tr><tr><td>C23</td><td>-0.0036 (4)</td><td>0.1967 (2)</td><td>0.41250 (19)</td><td>0.0660 (6)</td></tr><tr><td>H23</td><td>-0.0682</td><td>0.1094</td><td>0.4173</td><td>0.079*</td></tr><tr><td>C24</td><td>0.2138 (4)</td><td>0.2375 (2)</td><td>0.44168 (16)</td><td>0.0583 (6)</td></tr><tr><td>C25</td><td>0.3124 (4)</td><td>0.3650 (2)</td><td>0.43325 (16)</td><td>0.0565 (5)</td></tr><tr><td>H25</td><td>0.4605</td><td>0.3913</td><td>0.4526</td><td>0.068*</td></tr><tr><td>C26</td><td>0.1900 (4)</td><td>0.4544 (2)</td><td>0.39570 (15)</td><td>0.0536 (5)</td></tr><tr><td>H26</td><td>0.2579</td><td>0.5408</td><td>0.3892</td><td>0.064*</td></tr><tr><td>N1</td><td>-0.1697 (3)</td><td>0.51418 (19)</td><td>0.16948 (13)</td><td>0.0578 (5)</td></tr><tr><td>N2</td><td>-0.1687 (3)</td><td>0.50789 (19)</td><td>0.33683 (13)</td><td>0.0561 (5)</td></tr><tr><td>N3</td><td>0.0600 (4)</td><td>0.68403 (18)</td><td>0.26379 (14)</td><td>0.0615 (5)</td></tr><tr><td>C11</td><td>0.34990 (13)</td><td>0.13680 (7)</td><td>-0.00400 (5)</td><td>0.0841 (3)</td></tr><tr><td>C12</td><td>0.36408 (14)</td><td>0.12627 (7)</td><td>0.49405 (6)</td><td>0.0865 (3)</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>C1</td><td>0.0497 (13)</td><td>0.0749 (16)</td><td>0.0606 (14)</td><td>0.0138 (11)</td><td>0.0016 (10)</td><td>0.0033 (11)</td></tr><tr><td>C2</td><td>0.0733 (16)</td><td>0.0592 (14)</td><td>0.0614 (14)</td><td>0.0235 (12)</td><td>0.0035 (12)</td><td>-0.0017 (11)</td></tr><tr><td>C3</td><td>0.0750 (16)</td><td>0.0586 (14)</td><td>0.0659 (15)</td><td>0.0211 (12)</td><td>0.0029 (12)</td><td>0.0117 (11)</td></tr><tr><td>C4</td><td>0.108 (2)</td><td>0.0557 (15)</td><td>0.090 (2)</td><td>0.0095 (15)</td><td>0.0082 (18)</td><td>0.0044 (14)</td></tr><tr><td>C5</td><td>0.146 (4)</td><td>0.088 (2)</td><td>0.115 (3)</td><td>-0.010 (2)</td><td>0.040 (3)</td><td>-0.009 (2)</td></tr><tr><td>C6</td><td>0.173 (4)</td><td>0.088 (3)</td><td>0.115 (3)</td><td>-0.044 (3)</td><td>0.017 (3)</td><td>0.006 (2)</td></tr><tr><td>C11</td><td>0.0516 (12)</td><td>0.0559 (12)</td><td>0.0421 (10)</td><td>0.0039 (10)</td><td>-0.0054 (9)</td><td>0.0039 (9)</td></tr><tr><td>C12</td><td>0.0574 (13)</td><td>0.0499 (12)</td><td>0.0562 (12)</td><td>-0.0013 (10)</td><td>-0.0019 (10)</td><td>0.0039 (10)</td></tr><tr><td>C13</td><td>0.0545 (13)</td><td>0.0635 (14)</td><td>0.0572 (13)</td><td>0.0030 (11)</td><td>0.0037 (10)</td><td>0.0052 (11)</td></tr><tr><td>C14</td><td>0.0639 (14)</td><td>0.0586 (13)</td><td>0.0519 (12)</td><td>0.0084 (11)</td><td>-0.0040 (10)</td><td>-0.0039 (10)</td></tr><tr><td>C15</td><td>0.0691 (16)</td><td>0.0530 (14)</td><td>0.0799 (17)</td><td>-0.0045 (12)</td><td>-0.0021 (13)</td><td>-0.0076 (12)</td></tr><tr><td>C16</td><td>0.0536 (13)</td><td>0.0641 (15)</td><td>0.0778 (16)</td><td>-0.0036 (11)</td><td>0.0046 (12)</td><td>-0.0022 (12)</td></tr><tr><td>C21</td><td>0.0510 (12)</td><td>0.0533 (12)</td><td>0.0431 (11)</td><td>0.0077 (9)</td><td>0.0077 (9)</td><td>-0.0002 (9)</td></tr><tr><td>C22</td><td>0.0524 (13)</td><td>0.0587 (14)</td><td>0.0725 (15)</td><td>-0.0012 (11)</td><td>0.0051 (11)</td><td>0.0020 (11)</td></tr><tr><td>C23</td><td>0.0690 (16)</td><td>0.0492 (13)</td><td>0.0782 (16)</td><td>0.0015 (11)</td><td>0.0125 (13)</td><td>0.0071 (11)</td></tr><tr><td>C24</td><td>0.0664 (15)</td><td>0.0554 (13)</td><td>0.0564 (13)</td><td>0.0164 (11)</td><td>0.0126 (11)</td><td>0.0087 (10)</td></tr><tr><td>C25</td><td>0.0528 (12)</td><td>0.0610 (13)</td><td>0.0561 (13)</td><td>0.0102 (10)</td><td>0.0020 (10)</td><td>0.0024 (10)</td></tr></tbody></table>
<table><tr><td>H6B</td><td>0.5531</td><td>1.0364</td><td>0.1935</td><td>0.198*</td></tr><tr><td>H6C</td><td>0.5184</td><td>1.0117</td><td>0.2991</td><td>0.198*</td></tr><tr><td>C11</td><td>-0.0360 (4)</td><td>0.4255 (2)</td><td>0.13332 (14)</td><td>0.0505 (5)</td></tr><tr><td>C12</td><td>0.1801 (4)</td><td>0.4642 (2)</td><td>0.10651 (16)</td><td>0.0556 (5)</td></tr><tr><td>H12</td><td>0.2467</td><td>0.5511</td><td>0.1166</td><td>0.067*</td></tr><tr><td>C13</td><td>0.2992 (4)</td><td>0.3762 (2)</td><td>0.06492 (16)</td><td>0.0590 (6)</td></tr><tr><td>H13</td><td>0.4436</td><td>0.4041</td><td>0.0465</td><td>0.071*</td></tr><tr><td>C14</td><td>0.2027 (4)</td><td>0.2473 (2)</td><td>0.05101 (16)</td><td>0.0585 (6)</td></tr><tr><td>C15</td><td>-0.0100 (4)</td><td>0.2056 (2)</td><td>0.07759 (19)</td><td>0.0691 (7)</td></tr><tr><td>H15</td><td>-0.0742</td><td>0.1181</td><td>0.0685</td><td>0.083*</td></tr><tr><td>C16</td><td>-0.1281 (4)</td><td>0.2940 (2)</td><td>0.11776 (19)</td><td>0.0666 (6)</td></tr><tr><td>H16</td><td>-0.2732</td><td>0.2653</td><td>0.135</td><td>0.08*</td></tr><tr><td>C21</td><td>-0.0324 (4)</td><td>0.4175 (2)</td><td>0.36755 (14)</td><td>0.0491 (5)</td></tr><tr><td>C22</td><td>-0.1257 (4)</td><td>0.2865 (2)</td><td>0.37598 (18)</td><td>0.0622 (6)</td></tr><tr><td>H22</td><td>-0.2735</td><td>0.2589</td><td>0.3566</td><td>0.075*</td></tr><tr><td>C23</td><td>-0.0036 (4)</td><td>0.1967 (2)</td><td>0.41250 (19)</td><td>0.0660 (6)</td></tr><tr><td>H23</td><td>-0.0682</td><td>0.1094</td><td>0.4173</td><td>0.079*</td></tr><tr><td>C24</td><td>0.2138 (4)</td><td>0.2375 (2)</td><td>0.44168 (16)</td><td>0.0583 (6)</td></tr><tr><td>C25</td><td>0.3124 (4)</td><td>0.3650 (2)</td><td>0.43325 (16)</td><td>0.0565 (5)</td></tr><tr><td>H25</td><td>0.4605</td><td>0.3913</td><td>0.4526</td><td>0.068*</td></tr><tr><td>C26</td><td>0.1900 (4)</td><td>0.4544 (2)</td><td>0.39570 (15)</td><td>0.0536 (5)</td></tr><tr><td>H26</td><td>0.2579</td><td>0.5408</td><td>0.3892</td><td>0.064*</td></tr><tr><td>N1</td><td>-0.1697 (3)</td><td>0.51418 (19)</td><td>0.16948 (13)</td><td>0.0578 (5)</td></tr><tr><td>N2</td><td>-0.1687 (3)</td><td>0.50789 (19)</td><td>0.33683 (13)</td><td>0.0561 (5)</td></tr><tr><td>N3</td><td>0.0600 (4)</td><td>0.68403 (18)</td><td>0.26379 (14)</td><td>0.0615 (5)</td></tr><tr><td>C11</td><td>0.34990 (13)</td><td>0.13680 (7)</td><td>-0.00400 (5)</td><td>0.0841 (3)</td></tr><tr><td>C12</td><td>0.36408 (14)</td><td>0.12627 (7)</td><td>0.49405 (6)</td><td>0.0865 (3)</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>C1</td><td>0.0497 (13)</td><td>0.0749 (16)</td><td>0.0606 (14)</td><td>0.0138 (11)</td><td>0.0016 (10)</td><td>0.0033 (11)</td></tr><tr><td>C2</td><td>0.0733 (16)</td><td>0.0592 (14)</td><td>0.0614 (14)</td><td>0.0235 (12)</td><td>0.0035 (12)</td><td>-0.0017 (11)</td></tr><tr><td>C3</td><td>0.0750 (16)</td><td>0.0586 (14)</td><td>0.0659 (15)</td><td>0.0211 (12)</td><td>0.0029 (12)</td><td>0.0117 (11)</td></tr><tr><td>C4</td><td>0.108 (2)</td><td>0.0557 (15)</td><td>0.090 (2)</td><td>0.0095 (15)</td><td>0.0082 (18)</td><td>0.0044 (14)</td></tr><tr><td>C5</td><td>0.146 (4)</td><td>0.088 (2)</td><td>0.115 (3)</td><td>-0.010 (2)</td><td>0.040 (3)</td><td>-0.009 (2)</td></tr><tr><td>C6</td><td>0.173 (4)</td><td>0.088 (3)</td><td>0.115 (3)</td><td>-0.044 (3)</td><td>0.017 (3)</td><td>0.006 (2)</td></tr><tr><td>C11</td><td>0.0516 (12)</td><td>0.0559 (12)</td><td>0.0421 (10)</td><td>0.0039 (10)</td><td>-0.0054 (9)</td><td>0.0039 (9)</td></tr><tr><td>C12</td><td>0.0574 (13)</td><td>0.0499 (12)</td><td>0.0562 (12)</td><td>-0.0013 (10)</td><td>-0.0019 (10)</td><td>0.0039 (10)</td></tr><tr><td>C13</td><td>0.0545 (13)</td><td>0.0635 (14)</td><td>0.0572 (13)</td><td>0.0030 (11)</td><td>0.0037 (10)</td><td>0.0052 (11)</td></tr><tr><td>C14</td><td>0.0639 (14)</td><td>0.0586 (13)</td><td>0.0519 (12)</td><td>0.0084 (11)</td><td>-0.0040 (10)</td><td>-0.0039 (10)</td></tr><tr><td>C15</td><td>0.0691 (16)</td><td>0.0530 (14)</td><td>0.0799 (17)</td><td>-0.0045 (12)</td><td>-0.0021 (13)</td><td>-0.0076 (12)</td></tr><tr><td>C16</td><td>0.0536 (13)</td><td>0.0641 (15)</td><td>0.0778 (16)</td><td>-0.0036 (11)</td><td>0.0046 (12)</td><td>-0.0022 (12)</td></tr><tr><td>C21</td><td>0.0510 (12)</td><td>0.0533 (12)</td><td>0.0431 (11)</td><td>0.0077 (9)</td><td>0.0077 (9)</td><td>-0.0002 (9)</td></tr><tr><td>C22</td><td>0.0524 (13)</td><td>0.0587 (14)</td><td>0.0725 (15)</td><td>-0.0012 (11)</td><td>0.0051 (11)</td><td>0.0020 (11)</td></tr><tr><td>C23</td><td>0.0690 (16)</td><td>0.0492 (13)</td><td>0.0782 (16)</td><td>0.0015 (11)</td><td>0.0125 (13)</td><td>0.0071 (11)</td></tr><tr><td>C24</td><td>0.0664 (15)</td><td>0.0554 (13)</td><td>0.0564 (13)</td><td>0.0164 (11)</td><td>0.0126 (11)</td><td>0.0087 (10)</td></tr><tr><td>C25</td><td>0.0528 (12)</td><td>0.0610 (13)</td><td>0.0561 (13)</td><td>0.0102 (10)</td><td>0.0020 (10)</td><td>0.0024 (10)</td></tr></tbody></table>
<table><tr><td>C26</td><td>0.0562 (13)</td><td>0.0486 (12)</td><td>0.0541 (12)</td><td>0.0018 (10)</td><td>0.0059 (10)</td><td>0.0023 (9)</td></tr><tr><td>N1</td><td>0.0583 (11)</td><td>0.0619 (11)</td><td>0.0538 (11)</td><td>0.0113 (9)</td><td>-0.0016 (8)</td><td>0.0046 (9)</td></tr><tr><td>N2</td><td>0.0567 (11)</td><td>0.0603 (11)</td><td>0.0525 (10)</td><td>0.0130 (9)</td><td>0.0024 (8)</td><td>0.0000 (8)</td></tr><tr><td>N3</td><td>0.0734 (13)</td><td>0.0446 (10)</td><td>0.0665 (12)</td><td>0.0104 (9)</td><td>-0.0022 (10)</td><td>0.0023 (9)</td></tr><tr><td>Cl1</td><td>0.0883 (5)</td><td>0.0780 (5)</td><td>0.0872 (5)</td><td>0.0207 (4)</td><td>0.0049 (4)</td><td>-0.0199 (4)</td></tr><tr><td>Cl2</td><td>0.0940 (5)</td><td>0.0765 (5)</td><td>0.0981 (6)</td><td>0.0357 (4)</td><td>0.0131 (4)</td><td>0.0278 (4)</td></tr></table>

Geometric parameters (Å, °)

<table><tr><td>C1—N1</td><td>1.458 (3)</td><td>C11—C16</td><td>1.393 (3)</td></tr><tr><td>C1—N2</td><td>1.461 (3)</td><td>C11—N1</td><td>1.417 (3)</td></tr><tr><td>C1—H1A</td><td>0.97</td><td>C12—C13</td><td>1.384 (3)</td></tr><tr><td>C1—H1B</td><td>0.97</td><td>C12—H12</td><td>0.93</td></tr><tr><td>C2—N2</td><td>1.439 (3)</td><td>C13—C14</td><td>1.372 (3)</td></tr><tr><td>C2—N3</td><td>1.458 (3)</td><td>C13—H13</td><td>0.93</td></tr><tr><td>C2—H2A</td><td>0.97</td><td>C14—C15</td><td>1.368 (4)</td></tr><tr><td>C2—H2B</td><td>0.97</td><td>C14—Cl1</td><td>1.747 (2)</td></tr><tr><td>C3—N1</td><td>1.450 (3)</td><td>C15—C16</td><td>1.374 (4)</td></tr><tr><td>C3—N3</td><td>1.465 (3)</td><td>C15—H15</td><td>0.93</td></tr><tr><td>C3—H3A</td><td>0.97</td><td>C16—H16</td><td>0.93</td></tr><tr><td>C3—H3B</td><td>0.97</td><td>C21—C26</td><td>1.389 (3)</td></tr><tr><td>C4—C5</td><td>1.448 (5)</td><td>C21—C22</td><td>1.392 (3)</td></tr><tr><td>C4—N3</td><td>1.475 (3)</td><td>C21—N2</td><td>1.412 (3)</td></tr><tr><td>C4—H4A</td><td>0.97</td><td>C22—C23</td><td>1.380 (4)</td></tr><tr><td>C4—H4B</td><td>0.97</td><td>C22—H22</td><td>0.93</td></tr><tr><td>C5—C6</td><td>1.536 (4)</td><td>C23—C24</td><td>1.371 (4)</td></tr><tr><td>C5—H5A</td><td>0.97</td><td>C23—H23</td><td>0.93</td></tr><tr><td>C5—H5B</td><td>0.97</td><td>C24—C25</td><td>1.367 (3)</td></tr><tr><td>C6—H6A</td><td>0.96</td><td>C24—Cl2</td><td>1.747 (2)</td></tr><tr><td>C6—H6B</td><td>0.96</td><td>C25—C26</td><td>1.384 (3)</td></tr><tr><td>C6—H6C</td><td>0.96</td><td>C25—H25</td><td>0.93</td></tr><tr><td>C11—C12</td><td>1.383 (3)</td><td>C26—H26</td><td>0.93</td></tr><tr><td>N1—C1—N2</td><td>111.86 (19)</td><td>C13—C12—H12</td><td>119.3</td></tr><tr><td>N1—C1—H1A</td><td>109.2</td><td>C14—C13—C12</td><td>119.6 (2)</td></tr><tr><td>N2—C1—H1A</td><td>109.2</td><td>C14—C13—H13</td><td>120.2</td></tr><tr><td>N1—C1—H1B</td><td>109.2</td><td>C12—C13—H13</td><td>120.2</td></tr><tr><td>N2—C1—H1B</td><td>109.2</td><td>C15—C14—C13</td><td>120.5 (2)</td></tr><tr><td>H1A—C1—H1B</td><td>107.9</td><td>C15—C14—Cl1</td><td>119.76 (19)</td></tr><tr><td>N2—C2—N3</td><td>111.81 (18)</td><td>C13—C14—Cl1</td><td>119.70 (19)</td></tr><tr><td>N2—C2—H2A</td><td>109.3</td><td>C14—C15—C16</td><td>119.6 (2)</td></tr><tr><td>N3—C2—H2A</td><td>109.3</td><td>C14—C15—H15</td><td>120.2</td></tr><tr><td>N2—C2—H2B</td><td>109.3</td><td>C16—C15—H15</td><td>120.2</td></tr><tr><td>N3—C2—H2B</td><td>109.3</td><td>C15—C16—C11</td><td>121.7 (2)</td></tr><tr><td>H2A—C2—H2B</td><td>107.9</td><td>C15—C16—H16</td><td>119.1</td></tr><tr><td>N1—C3—N3</td><td>112.04 (19)</td><td>C11—C16—H16</td><td>119.1</td></tr><tr><td>N1—C3—H3A</td><td>109.2</td><td>C26—C21—C22</td><td>117.6 (2)</td></tr><tr><td>N3—C3—H3A</td><td>109.2</td><td>C26—C21—N2</td><td>123.0 (2)</td></tr></table>
<table><tr><td>C26</td><td>0.0562 (13)</td><td>0.0486 (12)</td><td>0.0541 (12)</td><td>0.0018 (10)</td><td>0.0059 (10)</td><td>0.0023 (9)</td></tr><tr><td>N1</td><td>0.0583 (11)</td><td>0.0619 (11)</td><td>0.0538 (11)</td><td>0.0113 (9)</td><td>-0.0016 (8)</td><td>0.0046 (9)</td></tr><tr><td>N2</td><td>0.0567 (11)</td><td>0.0603 (11)</td><td>0.0525 (10)</td><td>0.0130 (9)</td><td>0.0024 (8)</td><td>0.0000 (8)</td></tr><tr><td>N3</td><td>0.0734 (13)</td><td>0.0446 (10)</td><td>0.0665 (12)</td><td>0.0104 (9)</td><td>-0.0022 (10)</td><td>0.0023 (9)</td></tr><tr><td>Cl1</td><td>0.0883 (5)</td><td>0.0780 (5)</td><td>0.0872 (5)</td><td>0.0207 (4)</td><td>0.0049 (4)</td><td>-0.0199 (4)</td></tr><tr><td>Cl2</td><td>0.0940 (5)</td><td>0.0765 (5)</td><td>0.0981 (6)</td><td>0.0357 (4)</td><td>0.0131 (4)</td><td>0.0278 (4)</td></tr></table>

Geometric parameters (Å, °)

<table><tr><td>C1—N1</td><td>1.458 (3)</td><td>C11—C16</td><td>1.393 (3)</td></tr><tr><td>C1—N2</td><td>1.461 (3)</td><td>C11—N1</td><td>1.417 (3)</td></tr><tr><td>C1—H1A</td><td>0.97</td><td>C12—C13</td><td>1.384 (3)</td></tr><tr><td>C1—H1B</td><td>0.97</td><td>C12—H12</td><td>0.93</td></tr><tr><td>C2—N2</td><td>1.439 (3)</td><td>C13—C14</td><td>1.372 (3)</td></tr><tr><td>C2—N3</td><td>1.458 (3)</td><td>C13—H13</td><td>0.93</td></tr><tr><td>C2—H2A</td><td>0.97</td><td>C14—C15</td><td>1.368 (4)</td></tr><tr><td>C2—H2B</td><td>0.97</td><td>C14—Cl1</td><td>1.747 (2)</td></tr><tr><td>C3—N1</td><td>1.450 (3)</td><td>C15—C16</td><td>1.374 (4)</td></tr><tr><td>C3—N3</td><td>1.465 (3)</td><td>C15—H15</td><td>0.93</td></tr><tr><td>C3—H3A</td><td>0.97</td><td>C16—H16</td><td>0.93</td></tr><tr><td>C3—H3B</td><td>0.97</td><td>C21—C26</td><td>1.389 (3)</td></tr><tr><td>C4—C5</td><td>1.448 (5)</td><td>C21—C22</td><td>1.392 (3)</td></tr><tr><td>C4—N3</td><td>1.475 (3)</td><td>C21—N2</td><td>1.412 (3)</td></tr><tr><td>C4—H4A</td><td>0.97</td><td>C22—C23</td><td>1.380 (4)</td></tr><tr><td>C4—H4B</td><td>0.97</td><td>C22—H22</td><td>0.93</td></tr><tr><td>C5—C6</td><td>1.536 (4)</td><td>C23—C24</td><td>1.371 (4)</td></tr><tr><td>C5—H5A</td><td>0.97</td><td>C23—H23</td><td>0.93</td></tr><tr><td>C5—H5B</td><td>0.97</td><td>C24—C25</td><td>1.367 (3)</td></tr><tr><td>C6—H6A</td><td>0.96</td><td>C24—Cl2</td><td>1.747 (2)</td></tr><tr><td>C6—H6B</td><td>0.96</td><td>C25—C26</td><td>1.384 (3)</td></tr><tr><td>C6—H6C</td><td>0.96</td><td>C25—H25</td><td>0.93</td></tr><tr><td>C11—C12</td><td>1.383 (3)</td><td>C26—H26</td><td>0.93</td></tr><tr><td>N1—C1—N2</td><td>111.86 (19)</td><td>C13—C12—H12</td><td>119.3</td></tr><tr><td>N1—C1—H1A</td><td>109.2</td><td>C14—C13—C12</td><td>119.6 (2)</td></tr><tr><td>N2—C1—H1A</td><td>109.2</td><td>C14—C13—H13</td><td>120.2</td></tr><tr><td>N1—C1—H1B</td><td>109.2</td><td>C12—C13—H13</td><td>120.2</td></tr><tr><td>N2—C1—H1B</td><td>109.2</td><td>C15—C14—C13</td><td>120.5 (2)</td></tr><tr><td>H1A—C1—H1B</td><td>107.9</td><td>C15—C14—Cl1</td><td>119.76 (19)</td></tr><tr><td>N2—C2—N3</td><td>111.81 (18)</td><td>C13—C14—Cl1</td><td>119.70 (19)</td></tr><tr><td>N2—C2—H2A</td><td>109.3</td><td>C14—C15—C16</td><td>119.6 (2)</td></tr><tr><td>N3—C2—H2A</td><td>109.3</td><td>C14—C15—H15</td><td>120.2</td></tr><tr><td>N2—C2—H2B</td><td>109.3</td><td>C16—C15—H15</td><td>120.2</td></tr><tr><td>N3—C2—H2B</td><td>109.3</td><td>C15—C16—C11</td><td>121.7 (2)</td></tr><tr><td>H2A—C2—H2B</td><td>107.9</td><td>C15—C16—H16</td><td>119.1</td></tr><tr><td>N1—C3—N3</td><td>112.04 (19)</td><td>C11—C16—H16</td><td>119.1</td></tr><tr><td>N1—C3—H3A</td><td>109.2</td><td>C26—C21—C22</td><td>117.6 (2)</td></tr><tr><td>N3—C3—H3A</td><td>109.2</td><td>C26—C21—N2</td><td>123.0 (2)</td></tr></table>
<table>
  <tbody>
    <tr>
      <td>N1—C3—H3B</td>
      <td>109.2</td>
      <td>C22—C21—N2</td>
      <td>119.3 (2)</td>
    </tr>
    <tr>
      <td>N3—C3—H3B</td>
      <td>109.2</td>
      <td>C23—C22—C21</td>
      <td>121.4 (2)</td>
    </tr>
    <tr>
      <td>H3A—C3—H3B</td>
      <td>107.9</td>
      <td>C23—C22—H22</td>
      <td>119.3</td>
    </tr>
    <tr>
      <td>C5—C4—N3</td>
      <td>113.4 (3)</td>
      <td>C21—C22—H22</td>
      <td>119.3</td>
    </tr>
    <tr>
      <td>C5—C4—H4A</td>
      <td>108.9</td>
      <td>C24—C23—C22</td>
      <td>119.4 (2)</td>
    </tr>
    <tr>
      <td>N3—C4—H4A</td>
      <td>108.9</td>
      <td>C24—C23—H23</td>
      <td>120.3</td>
    </tr>
    <tr>
      <td>C5—C4—H4B</td>
      <td>108.9</td>
      <td>C22—C23—H23</td>
      <td>120.3</td>
    </tr>
    <tr>
      <td>N3—C4—H4B</td>
      <td>108.9</td>
      <td>C25—C24—C23</td>
      <td>120.9 (2)</td>
    </tr>
    <tr>
      <td>H4A—C4—H4B</td>
      <td>107.7</td>
      <td>C25—C24—Cl2</td>
      <td>119.54 (19)</td>
    </tr>
    <tr>
      <td>C4—C5—C6</td>
      <td>112.8 (3)</td>
      <td>C23—C24—Cl2</td>
      <td>119.48 (19)</td>
    </tr>
    <tr>
      <td>C4—C5—H5A</td>
      <td>109</td>
      <td>C24—C25—C26</td>
      <td>119.5 (2)</td>
    </tr>
    <tr>
      <td>C6—C5—H5A</td>
      <td>109</td>
      <td>C24—C25—H25</td>
      <td>120.2</td>
    </tr>
    <tr>
      <td>C4—C5—H5B</td>
      <td>109</td>
      <td>C26—C25—H25</td>
      <td>120.2</td>
    </tr>
    <tr>
      <td>C6—C5—H5B</td>
      <td>109</td>
      <td>C25—C26—C21</td>
      <td>121.2 (2)</td>
    </tr>
    <tr>
      <td>H5A—C5—H5B</td>
      <td>107.8</td>
      <td>C25—C26—H26</td>
      <td>119.4</td>
    </tr>
    <tr>
      <td>C5—C6—H6A</td>
      <td>109.5</td>
      <td>C21—C26—H26</td>
      <td>119.4</td>
    </tr>
    <tr>
      <td>C5—C6—H6B</td>
      <td>109.5</td>
      <td>C11—N1—C3</td>
      <td>118.73 (19)</td>
    </tr>
    <tr>
      <td>H6A—C6—H6B</td>
      <td>109.5</td>
      <td>C11—N1—C1</td>
      <td>118.44 (19)</td>
    </tr>
    <tr>
      <td>C5—C6—H6C</td>
      <td>109.5</td>
      <td>C3—N1—C1</td>
      <td>109.38 (19)</td>
    </tr>
    <tr>
      <td>H6A—C6—H6C</td>
      <td>109.5</td>
      <td>C21—N2—C2</td>
      <td>118.41 (19)</td>
    </tr>
    <tr>
      <td>H6B—C6—H6C</td>
      <td>109.5</td>
      <td>C21—N2—C1</td>
      <td>118.07 (18)</td>
    </tr>
    <tr>
      <td>C12—C11—C16</td>
      <td>117.3 (2)</td>
      <td>C2—N2—C1</td>
      <td>109.76 (19)</td>
    </tr>
    <tr>
      <td>C12—C11—N1</td>
      <td>123.2 (2)</td>
      <td>C2—N3—C3</td>
      <td>108.2 (2)</td>
    </tr>
    <tr>
      <td>C16—C11—N1</td>
      <td>119.4 (2)</td>
      <td>C2—N3—C4</td>
      <td>108.2 (2)</td>
    </tr>
    <tr>
      <td>C11—C12—C13</td>
      <td>121.3 (2)</td>
      <td>C3—N3—C4</td>
      <td>112.7 (2)</td>
    </tr>
    <tr>
      <td>C11—C12—H12</td>
      <td>119.3</td>
      <td></td>
      <td></td>
    </tr>
  </tbody>
</table>

<table>
  <tbody>
    <tr>
      <td>N3—C4—C5—C6</td>
      <td>-170.1 (3)</td>
      <td>C16—C11—N1—C3</td>
      <td>-175.1 (2)</td>
    </tr>
    <tr>
      <td>C16—C11—C12—C13</td>
      <td>0.7 (3)</td>
      <td>C12—C11—N1—C1</td>
      <td>-136.1 (2)</td>
    </tr>
    <tr>
      <td>N1—C11—C12—C13</td>
      <td>-175.0 (2)</td>
      <td>C16—C11—N1—C1</td>
      <td>48.3 (3)</td>
    </tr>
    <tr>
      <td>C11—C12—C13—C14</td>
      <td>-0.9 (3)</td>
      <td>N3—C3—N1—C11</td>
      <td>-83.0 (3)</td>
    </tr>
    <tr>
      <td>C12—C13—C14—C15</td>
      <td>0.2 (4)</td>
      <td>N3—C3—N1—C1</td>
      <td>57.2 (3)</td>
    </tr>
    <tr>
      <td>C12—C13—C14—C11</td>
      <td>178.45 (18)</td>
      <td>N2—C1—N1—C11</td>
      <td>84.7 (2)</td>
    </tr>
    <tr>
      <td>C13—C14—C15—C16</td>
      <td>0.6 (4)</td>
      <td>N2—C1—N1—C3</td>
      <td>-55.7 (3)</td>
    </tr>
    <tr>
      <td>C11—C14—C15—C16</td>
      <td>-177.6 (2)</td>
      <td>C26—C21—N2—C2</td>
      <td>-5.2 (3)</td>
    </tr>
    <tr>
      <td>C14—C15—C16—C11</td>
      <td>-0.8 (4)</td>
      <td>C22—C21—N2—C2</td>
      <td>170.6 (2)</td>
    </tr>
    <tr>
      <td>C12—C11—C16—C15</td>
      <td>0.1 (4)</td>
      <td>C26—C21—N2—C1</td>
      <td>131.2 (2)</td>
    </tr>
    <tr>
      <td>N1—C11—C16—C15</td>
      <td>176.0 (2)</td>
      <td>C22—C21—N2—C1</td>
      <td>-53.0 (3)</td>
    </tr>
    <tr>
      <td>C26—C21—C22—C23</td>
      <td>1.2 (3)</td>
      <td>N3—C2—N2—C21</td>
      <td>81.6 (2)</td>
    </tr>
    <tr>
      <td>N2—C21—C22—C23</td>
      <td>-174.9 (2)</td>
      <td>N3—C2—N2—C1</td>
      <td>-58.1 (3)</td>
    </tr>
    <tr>
      <td>C21—C22—C23—C24</td>
      <td>0.4 (4)</td>
      <td>N1—C1—N2—C21</td>
      <td>-83.5 (3)</td>
    </tr>
    <tr>
      <td>C22—C23—C24—C25</td>
      <td>-1.4 (4)</td>
      <td>N1—C1—N2—C2</td>
      <td>56.4 (3)</td>
    </tr>
    <tr>
      <td>C22—C23—C24—C12</td>
      <td>176.34 (19)</td>
      <td>N2—C2—N3—C3</td>
      <td>58.6 (2)</td>
    </tr>
    <tr>
      <td>C23—C24—C25—C26</td>
      <td>0.7 (4)</td>
      <td>N2—C2—N3—C4</td>
      <td>-179.0 (2)</td>
    </tr>
    <tr>
      <td>C12—C24—C25—C26</td>
      <td>-177.02 (17)</td>
      <td>N1—C3—N3—C2</td>
      <td>-58.3 (3)</td>
    </tr>
    <tr>
      <td>C24—C25—C26—C21</td>
      <td>0.9 (3)</td>
      <td>N1—C3—N3—C4</td>
      <td>-177.8 (2)</td>
    </tr>
    <tr>
      <td>C22—C21—C26—C25</td>
      <td>-1.8 (3)</td>
      <td>C5—C4—N3—C2</td>
      <td>166.4 (3)</td>
    </tr>
    <tr>
      <td>N2—C21—C26—C25</td>
      <td>174.05 (19)</td>
      <td>C5—C4—N3—C3</td>
      <td>-74.0 (4)</td>
    </tr>
  </tbody>
</table>
<table>
  <tbody>
    <tr>
      <td>N1—C3—H3B</td>
      <td>109.2</td>
      <td>C22—C21—N2</td>
      <td>119.3 (2)</td>
    </tr>
    <tr>
      <td>N3—C3—H3B</td>
      <td>109.2</td>
      <td>C23—C22—C21</td>
      <td>121.4 (2)</td>
    </tr>
    <tr>
      <td>H3A—C3—H3B</td>
      <td>107.9</td>
      <td>C23—C22—H22</td>
      <td>119.3</td>
    </tr>
    <tr>
      <td>C5—C4—N3</td>
      <td>113.4 (3)</td>
      <td>C21—C22—H22</td>
      <td>119.3</td>
    </tr>
    <tr>
      <td>C5—C4—H4A</td>
      <td>108.9</td>
      <td>C24—C23—C22</td>
      <td>119.4 (2)</td>
    </tr>
    <tr>
      <td>N3—C4—H4A</td>
      <td>108.9</td>
      <td>C24—C23—H23</td>
      <td>120.3</td>
    </tr>
    <tr>
      <td>C5—C4—H4B</td>
      <td>108.9</td>
      <td>C22—C23—H23</td>
      <td>120.3</td>
    </tr>
    <tr>
      <td>N3—C4—H4B</td>
      <td>108.9</td>
      <td>C25—C24—C23</td>
      <td>120.9 (2)</td>
    </tr>
    <tr>
      <td>H4A—C4—H4B</td>
      <td>107.7</td>
      <td>C25—C24—Cl2</td>
      <td>119.54 (19)</td>
    </tr>
    <tr>
      <td>C4—C5—C6</td>
      <td>112.8 (3)</td>
      <td>C23—C24—Cl2</td>
      <td>119.48 (19)</td>
    </tr>
    <tr>
      <td>C4—C5—H5A</td>
      <td>109</td>
      <td>C24—C25—C26</td>
      <td>119.5 (2)</td>
    </tr>
    <tr>
      <td>C6—C5—H5A</td>
      <td>109</td>
      <td>C24—C25—H25</td>
      <td>120.2</td>
    </tr>
    <tr>
      <td>C4—C5—H5B</td>
      <td>109</td>
      <td>C26—C25—H25</td>
      <td>120.2</td>
    </tr>
    <tr>
      <td>C6—C5—H5B</td>
      <td>109</td>
      <td>C25—C26—C21</td>
      <td>121.2 (2)</td>
    </tr>
    <tr>
      <td>H5A—C5—H5B</td>
      <td>107.8</td>
      <td>C25—C26—H26</td>
      <td>119.4</td>
    </tr>
    <tr>
      <td>C5—C6—H6A</td>
      <td>109.5</td>
      <td>C21—C26—H26</td>
      <td>119.4</td>
    </tr>
    <tr>
      <td>C5—C6—H6B</td>
      <td>109.5</td>
      <td>C11—N1—C3</td>
      <td>118.73 (19)</td>
    </tr>
    <tr>
      <td>H6A—C6—H6B</td>
      <td>109.5</td>
      <td>C11—N1—C1</td>
      <td>118.44 (19)</td>
    </tr>
    <tr>
      <td>C5—C6—H6C</td>
      <td>109.5</td>
      <td>C3—N1—C1</td>
      <td>109.38 (19)</td>
    </tr>
    <tr>
      <td>H6A—C6—H6C</td>
      <td>109.5</td>
      <td>C21—N2—C2</td>
      <td>118.41 (19)</td>
    </tr>
    <tr>
      <td>H6B—C6—H6C</td>
      <td>109.5</td>
      <td>C21—N2—C1</td>
      <td>118.07 (18)</td>
    </tr>
    <tr>
      <td>C12—C11—C16</td>
      <td>117.3 (2)</td>
      <td>C2—N2—C1</td>
      <td>109.76 (19)</td>
    </tr>
    <tr>
      <td>C12—C11—N1</td>
      <td>123.2 (2)</td>
      <td>C2—N3—C3</td>
      <td>108.2 (2)</td>
    </tr>
    <tr>
      <td>C16—C11—N1</td>
      <td>119.4 (2)</td>
      <td>C2—N3—C4</td>
      <td>108.2 (2)</td>
    </tr>
    <tr>
      <td>C11—C12—C13</td>
      <td>121.3 (2)</td>
      <td>C3—N3—C4</td>
      <td>112.7 (2)</td>
    </tr>
    <tr>
      <td>C11—C12—H12</td>
      <td>119.3</td>
      <td></td>
      <td></td>
    </tr>
  </tbody>
</table>

<table>
  <tbody>
    <tr>
      <td>N3—C4—C5—C6</td>
      <td>-170.1 (3)</td>
      <td>C16—C11—N1—C3</td>
      <td>-175.1 (2)</td>
    </tr>
    <tr>
      <td>C16—C11—C12—C13</td>
      <td>0.7 (3)</td>
      <td>C12—C11—N1—C1</td>
      <td>-136.1 (2)</td>
    </tr>
    <tr>
      <td>N1—C11—C12—C13</td>
      <td>-175.0 (2)</td>
      <td>C16—C11—N1—C1</td>
      <td>48.3 (3)</td>
    </tr>
    <tr>
      <td>C11—C12—C13—C14</td>
      <td>-0.9 (3)</td>
      <td>N3—C3—N1—C11</td>
      <td>-83.0 (3)</td>
    </tr>
    <tr>
      <td>C12—C13—C14—C15</td>
      <td>0.2 (4)</td>
      <td>N3—C3—N1—C1</td>
      <td>57.2 (3)</td>
    </tr>
    <tr>
      <td>C12—C13—C14—C11</td>
      <td>178.45 (18)</td>
      <td>N2—C1—N1—C11</td>
      <td>84.7 (2)</td>
    </tr>
    <tr>
      <td>C13—C14—C15—C16</td>
      <td>0.6 (4)</td>
      <td>N2—C1—N1—C3</td>
      <td>-55.7 (3)</td>
    </tr>
    <tr>
      <td>C11—C14—C15—C16</td>
      <td>-177.6 (2)</td>
      <td>C26—C21—N2—C2</td>
      <td>-5.2 (3)</td>
    </tr>
    <tr>
      <td>C14—C15—C16—C11</td>
      <td>-0.8 (4)</td>
      <td>C22—C21—N2—C2</td>
      <td>170.6 (2)</td>
    </tr>
    <tr>
      <td>C12—C11—C16—C15</td>
      <td>0.1 (4)</td>
      <td>C26—C21—N2—C1</td>
      <td>131.2 (2)</td>
    </tr>
    <tr>
      <td>N1—C11—C16—C15</td>
      <td>176.0 (2)</td>
      <td>C22—C21—N2—C1</td>
      <td>-53.0 (3)</td>
    </tr>
    <tr>
      <td>C26—C21—C22—C23</td>
      <td>1.2 (3)</td>
      <td>N3—C2—N2—C21</td>
      <td>81.6 (2)</td>
    </tr>
    <tr>
      <td>N2—C21—C22—C23</td>
      <td>-174.9 (2)</td>
      <td>N3—C2—N2—C1</td>
      <td>-58.1 (3)</td>
    </tr>
    <tr>
      <td>C21—C22—C23—C24</td>
      <td>0.4 (4)</td>
      <td>N1—C1—N2—C21</td>
      <td>-83.5 (3)</td>
    </tr>
    <tr>
      <td>C22—C23—C24—C25</td>
      <td>-1.4 (4)</td>
      <td>N1—C1—N2—C2</td>
      <td>56.4 (3)</td>
    </tr>
    <tr>
      <td>C22—C23—C24—C12</td>
      <td>176.34 (19)</td>
      <td>N2—C2—N3—C3</td>
      <td>58.6 (2)</td>
    </tr>
    <tr>
      <td>C23—C24—C25—C26</td>
      <td>0.7 (4)</td>
      <td>N2—C2—N3—C4</td>
      <td>-179.0 (2)</td>
    </tr>
    <tr>
      <td>C12—C24—C25—C26</td>
      <td>-177.02 (17)</td>
      <td>N1—C3—N3—C2</td>
      <td>-58.3 (3)</td>
    </tr>
    <tr>
      <td>C24—C25—C26—C21</td>
      <td>0.9 (3)</td>
      <td>N1—C3—N3—C4</td>
      <td>-177.8 (2)</td>
    </tr>
    <tr>
      <td>C22—C21—C26—C25</td>
      <td>-1.8 (3)</td>
      <td>C5—C4—N3—C2</td>
      <td>166.4 (3)</td>
    </tr>
    <tr>
      <td>N2—C21—C26—C25</td>
      <td>174.05 (19)</td>
      <td>C5—C4—N3—C3</td>
      <td>-74.0 (4)</td>
    </tr>
  </tbody>
</table>
C12—C11—N1—C3 0.5 (3)

Hydrogen-bond geometry (Å, °)

<table><tr><td>D—H···A</td><td>D—H</td><td>H···A</td><td>D···A</td><td>D—H···A</td></tr><tr><td>C2—H2A···Cg<sup>i</sup></td><td>0.96</td><td>2.92</td><td>3.668 (3)</td><td>134</td></tr></table>

Symmetry code: (i) -x, -y+1, -z+1.
C12—C11—N1—C3 0.5 (3)

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>C2—H2A···Cg<sup>i</sup></td><td>0.96</td><td>2.92</td><td>3.668 (3)</td><td>134</td></tr></tbody></table>

Symmetry code: (i) -x, -y+1, -z+1.