Coupling between 2-pyridyl­selenyl chloride and phenyl­seleno­cyanate: synthesis, crystal structure and non-covalent inter­actions

Temesgen, A.W.; Tskhovrebov, A.G.; Artemjev, A.A.; Kubasov, A.S.; Novikov, A.S.; Borisov, A.V.; Kirichuk, A.A.; Kritchenkov, A.S.; Le, T.A.

doi:10.1107/S2056989024008831

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Volume 80| Part 10| October 2024| Pages 1024-1028

https://doi.org/10.1107/S2056989024008831

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Coupling between 2-pyridylselenyl chloride and phenylselenocyanate: synthesis, crystal structure and non-covalent interactions

Ayalew W. Temesgen,^a Alexander G. Tskhovrebov,^b Alexey A. Artemjev,^b Alexey S. Kubasov,^c Alexander S. Novikov,^d Alexander V. Borisov,^e Anatoly A. Kirichuk,^b Andreii S. Kritchenkov ^b and Tuan Anh Le ^f ^*

^aDepartment of Chemistry, College of Natural and Computational Science, University of Gondar, Gondar 196, Ethiopia, ^bPeople's Friendship University of Russia, 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation, ^cKurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 31, 119071, Moscow, Russian Federation, ^dInstitute of Chemistry, Saint Petersburg State University, Universitetskaya, Nab., 7/9, 199034 Saint Petersburg, Russian Federation, ^eR.E. Alekseev Nizhny Novgorod State Technical University, Minin St., 24, Nizhny, Novgorod, Russian Federation, and ^fUniversity of Science, Vietnam National University, Hanoi, 334 Nguyen Trai, Thanh Xuan, Hanoi, 100000, Vietnam
^*Correspondence e-mail: wodajo.ayalew@uog.edu.et

Edited by J. M. Delgado, Universidad de Los Andes, Venezuela (Received 14 November 2023; accepted 10 September 2024; online 17 September 2024)

This article is part of a collection of articles to commemorate the founding of the African Crystallographic Association and the 75th anniversary of the IUCr.

A new pyridine-fused selenodiazolium salt, 3-(phenylselanyl)[1,2,4]selenadiazolo[4,5-a]pyridin-4-ylium chloride dichloromethane 0.352-solvate, C₁₂H₉N₂Se₂⁺·Cl⁻·0.352CH₂Cl₂, was obtained from the reaction between 2-pyridylselenenyl chloride and phenylselenocyanate. Single-crystal structural analysis revealed the presence of C—H⋯N, C—H⋯Cl⁻, C—H⋯Se hydrogen bonds as well as chalcogen–chalcogen (Se⋯Se) and chalcogen–halogen (Se⋯Cl⁻) interactions. Non-covalent interactions were explored by DFT calculations followed by topological analysis of the electron density distribution (QTAIM analysis). The structure consists of pairs of selenodiazolium moieties arranged in a head-to-tail fashion surrounding disordered dichloromethane molecules. The assemblies are connected by C—H⋯Cl⁻ and C—H⋯N hydrogen bonds, forming layers, which stack along the c-axis direction connected by bifurcated Se⋯Cl⁻⋯H—C interactions.

Keywords: crystal structure; non-covalent interactions; chalcogen heterocycles; chalcogen bonding.

CCDC reference: 2382988

1. Chemical context

Recently, a novel cycloaddition reaction between nitriles and 2-pyridylselenyl reagents was described (Khrustalev et al., 2021 ). What makes this finding particularly notable is that the reaction takes place under mild conditions, displaying a high degree of chemoselectivity (Grudova et al., 2022 ; Artemjev et al., 2023 ). As a result, pyridinium-fused selenodiazolium salts are formed with excellent yields.

As part of our ongoing project to investigate the reactivity of bifunctional 2-pyridylselenyl reagents (Grudova et al., 2022; Artemjev et al., 2022 , 2023; Sapronov et al., 2023 ) we have recently expanded our research to explore the chemistry of addition to the C≡N triple bond involving a different category of nitrile substrates known as cyanamides or push–pull nitriles. Push–pull structures are characterized by high polarization and consist of an electron-withdrawing substituent or electronegative atom on one side of the multiple bond and an electron-donating group on the opposite side (Le Questel et al., 2000 ; Gushchin et al., 2009 ; Kritchenkov et al., 2011 ).

Here we show that 2-pyridylselenyl chloride reacts efficiently with phenylselenocyanate furnishing a cationic pyridinium-fused 1,2,4-selenodiazole in high yield. This finding is another illustration of the remarkable propensity of bifunctional 2-pyridylselenyl reagents to engage in dipolar cycloaddition with the CN triple bond, displaying a high degree of chemoselectivity. The title compound was synthesized in high yield in CH₂Cl₂ according to the scheme.

2. Structural commentary

Crystals suitable for X-ray analysis were obtained directly from the reaction mixture. The compound crystallized as colorless blocks in space group P2₁/c. The asymmetric unit (Fig. 1) contains one cation, one Cl⁻ anion and a disordered CH₂Cl₂ molecule. The 1,2,4-selenodiazole fragment is almost planar (r.m.s.d. = 0.017 Å) and makes an angle of 81.64 (16)° with the phenylselenyl ring. The Se1—N2 and Se1—C1 bond lengths are 1.863 (4) and 1.877 (4) Å, respectively, and the Se1⋯Cl1 distance is 2.9325 (17). These bond distances are similar to those reported in previous work on 1,2,4-selenodiazoles (Grudova et al., 2022; Artemjev et al., 2022, 2023; Sapronov et al., 2022 , 2023). The Se2—C6 and Se2—C7 bond lengths are typical for Se—C_ar bonds [1.926 (5) Å and 1.946 (5) Å, respectively]. The C7—Se2—C6—N1 and C6—Se2—C7—C12 torsion angles are 93.4 (5) and 76.9 (4)°, respectively.

Figure 1
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features

The crystal packing is shown in Fig. 2, viewed down the b axis. In the crystal, pairs of selenodiazolium moieties are arranged in a head-to-tail fashion surrounding disordered dichloromethane molecules. C—H⋯Cl⁻ and C—H⋯N hydrogen bonds (Table 1) connect these units to form layers parallel to the ac plane. In addition, π–π stacking interactions between the phenyl rings of two neighboring molecules occur. The layers are interconnected via bifurcated Se⋯Cl⁻⋯H—C interactions and stack along the c-axis.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cl1	0.95	2.60	3.297 (5)	131
C3—H3⋯Cl1ⁱ	0.95	2.60	3.526 (5)	167
C5—H5⋯Se2	0.95	2.82	3.242 (5)	108
C5—H5⋯N2ⁱⁱ	0.95	2.45	3.179 (6)	134
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
View along the b axis of the crystal packing of the title compound.

To further understand the nature of the interactions and to quantify the strength of the bifurcated chalcogen–halogen–hydrogen contacts, Se⋯Cl⁻⋯H—C, and the interactions involving the Se atom (Se⋯Se and Se⋯Cl⁻) in the crystal structure, DFT calculations followed by a topological analysis of the electron-density distribution (QTAIM analysis) were carried out at the ωB97XD/6-311++G** level of theory for the model structure (see Computational details and Table S1 in the supporting information). The results of the QTAIM analysis are summarized in Table S1. The contour line diagrams of the Laplacian of the electron density distribution Ñ²r(r), bond paths, and selected zero-flux surfaces, visualization of electron localization function (ELF) and reduced density gradient (RDG) analyses for bifurcated Se⋯Cl⁻⋯H—C, Se⋯Se and Se⋯Cl⁻ interactions in the crystal structure are shown in Figs. 3 and 4, respectively.

Figure 3
Contour line diagram of the Laplacian of the electron-density distribution Ñ²r(r), bond paths, and selected zero-flux surfaces (left panel), visualization of the electron localization function (ELF, center panel) and reduced density gradient (RDG, right panel) analyses for bifurcated chalcogen-hydrogen bonding Se⋯Cl⁻⋯H—C (contacts Se1⋯Cl1⁻ 2.9325 (17) Å and C2—H2⋯Cl⁻ 2.60 Å) in the crystal structure. Bond critical points (3, −1) are shown in blue, nuclear critical points (3, −3) in pale brown, ring critical points (3, +1) in orange, bond paths are shown as pale brown lines, length units in Å, and the color scale for the ELF and RDG maps is presented in a.u.

Figure 4
Contour line diagram of the Laplacian of the electron-density distribution Ñ²r(r), bond paths, and selected zero-flux surfaces (left panel), visualization of the electron localization function (ELF, center panel) and reduced density gradient (RDG, right panel) analyses for chalcogen bonding Se2⋯Se1ⁱ [3.9426 (18) Å; symmetry code: (i) x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z], Se2⋯Cl1^–ii [3.229 (2) Å; symmetry code: (ii) −x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z] and Se1⋯Cl1^–iii [3.3805 (19) Å; symmetry code: (iii) −x, 1 − y, −z] in the crystal structure. Bond critical points (3, −1) are shown in blue, nuclear critical points (3, −3) in pale brown, ring critical points (3, +1) in orange, bond paths are shown as pale brown lines, length units in Å, and the color scale for the ELF and RDG maps is presented in a.u.

The QTAIM analysis of the model structure demonstrates the presence of bond critical points (3, −1) for short contacts Se⋯Cl⁻, C–H⋯Cl⁻ and Se⋯Se in the crystal structure (Table S1 and Figs. 3 and 4) (Bondi et al., 1966 ). The low magnitude of the electron density, the positive values of the Laplacian of the electron density and zero or very close to zero values of the energy density in these bond critical points (3, −1) and estimated strength for appropriate short contacts are typical for weak purely non-covalent [–G(r)/V(r) > 1; Espinosa et al., 2002 ] interactions. The Laplacian of the electron density is typically decomposed into the sum of contributions along the three principal axes of maximal variation. The three eigenvalues of the Hessian matrix (λ₁, λ₂ and λ₃) and the sign of λ₂ can be utilized to distinguish bonding (attractive, λ₂ < 0) weak interactions from non-bonding ones (repulsive, λ₂ > 0) (Johnson et al., 2010 ; Contreras-García et al., 2011 ). Thus, the discussed short contacts Se⋯Cl⁻, C–H⋯Cl⁻ and Se⋯Se in the structure are attractive.

4. Database survey

A search in the Cambridge Structural Database (CSD, Version 5.43, update of Sep. 2022; Groom et al., 2016 ) showed only 16 hits for 1,2,4-selenodiazolium salts, which differ not only in the type of nitrile fragment (Me: EWEPUU, Khrustalev et al., 2021; Ph: NAQDES, Buslov et al., 2021 ; BrC₆H₄: EWEQEF, Khrustalev et al., 2021), but also in the anion (CF₃COO–: YEJXEU; AuCl₄–: YEJXUK; and ReO₄⁻: YEJYAR, Artemjev et al., 2022).

5. Synthesis and crystallization

General remarks. All manipulations were carried out in air. All the reagents used in this study were obtained from commercial sources (Aldrich, TCI-Europe, Strem, ABCR). Commercially available solvents were purified by conventional methods and distilled right before they were used. NMR spectra were recorded on a Bruker Advance Neo (¹H: 700 MHz); chemical shifts (δ) are given in ppm, coupling constants (J) in Hz. 2-Pyridylselenyl chloride was synthesized by our method (Artemjev et al., 2022; Artemjev et al., 2023).

A solution of phenylselenocyanate (0.16 mmol, 20 µL) in CH₂Cl₂ (1 mL) was added to a suspension of 2-pyridylselenyl chloride (0.13 mmol, 25.3 mg) in CH₂Cl₂ (2 mL) and the mixture was kept at room temperature for 6 h without stirring. The formed colorless precipitate was centrifuged, washed with CH₂Cl₂ (1 mL), Et₂O (3 × 1 mL) and dried under vacuum. Yield 34.5 mg (70%). ¹H NMR (700 MHz, D₂O) δ 9.53 (d, J = 6.8 Hz, 1H, H5), 8.82 (d, J = 8.6 Hz, 1H, H8), 8.42 (t, J = 7.9 Hz, 1H, H7), 8.05 (t, J = 7.0 Hz, 1H, H6), 7.82 (d, J = 7.6 Hz, 2H, H2′), 7.55 (t, J = 7.5 Hz, 1H, H4′), 7.49 (t, J = 7.7 Hz, 2H, H3′). ¹³C NMR (176 MHz, D₂O) δ 168.1 (C3), 148.8 (C9), 139.9 (C5), 137.4 (C8), 135.7 (C2′), 130.5 (C4′), 130.3 (C3′), 126.0 (C7), 123.8 (C1′), 123.2 (C6). Crystals suitable for X-ray analysis were obtained directly from the reaction mixture.

The single-point calculations based on the experimental X-ray structure were carried out at the DFT level of theory using the dispersion-corrected hybrid functional ωB97XD (Chai et al., 2008 ) with the Gaussian-09 (Frisch et al., 2010 ) program package. The 6-311++G** basis sets were used for all atoms. The topological analysis of the electron density distribution was performed using the Multiwfn program (version 3.7; Lu et al., 2012 ). The Cartesian atomic coordinates for the model structure are presented in Table S1 of the supporting information.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were included in calculated positions (C—H = 0.95–1.00 Å) and refined as riding with U_iso(H) = 1.2U_eq(C). The dichloromethane molecule is disordered around a center of symmetry and refined to a total occupancy of 70%. Residual electron density of 1.5 e Å⁻³ remained at the center of symmetry. Attempts to rationalize it did not produce a plausible model nor an improved refinement.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₉N₂Se₂⁺·Cl⁻·0.352CH₂Cl₂
M_r	404.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.087 (3), 11.758 (5), 11.991 (3)
β (°)	115.337 (6)
V (Å³)	1412.8 (8)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	5.54
Crystal size (mm)	0.20 × 0.10 × 0.08

Data collection
Diffractometer	Bruker D8 Venture
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.466, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	7927, 3394, 2649
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.088, 1.06
No. of reflections	3394
No. of parameters	182
No. of restraints	20
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.50, −0.92
Computer programs: APEX2 and SAINT (Bruker, 2019 ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2382988

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024008831/jw2003sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024008831/jw2003Isup2.hkl

QTAIM analysis. DOI: https://doi.org/10.1107/S2056989024008831/jw2003sup4.docx

checkCIF report

Computing details top

3-(Phenylselanyl)[1,2,4]selenadiazolo[4,5-a]pyridin-4-ylium chloride dichloromethane top

Crystal data top

C₁₂H₉N₂Se₂⁺·Cl⁻·0.352CH₂Cl₂	F(000) = 779
M_r = 404.50	D_x = 1.902 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.087 (3) Å	Cell parameters from 3887 reflections
b = 11.758 (5) Å	θ = 2.6–28.0°
c = 11.991 (3) Å	µ = 5.54 mm⁻¹
β = 115.337 (6)°	T = 100 K
V = 1412.8 (8) Å³	Block, colourless
Z = 4	0.20 × 0.10 × 0.08 mm

Data collection top

Bruker D8 Venture diffractometer	2649 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.038
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 28.0°, θ_min = 2.0°
T_min = 0.466, T_max = 0.746	h = −12→14
7927 measured reflections	k = −12→15
3394 independent reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: mixed
wR(F²) = 0.088	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0153P)² + 6.8557P] where P = (F_o² + 2F_c²)/3
3394 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 1.50 e Å⁻³
20 restraints	Δρ_min = −0.91 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Se1	0.10761 (5)	0.56698 (4)	0.17359 (4)	0.01592 (12)
Se2	0.24558 (5)	0.87121 (4)	0.42629 (4)	0.01426 (12)
N1	0.1762 (4)	0.6289 (3)	0.4071 (4)	0.0132 (8)
N2	0.1584 (4)	0.7155 (3)	0.2272 (4)	0.0162 (8)
C1	0.1373 (4)	0.5329 (4)	0.3362 (4)	0.0121 (9)
C2	0.1221 (5)	0.4305 (4)	0.3880 (4)	0.0150 (9)
H2	0.095583	0.363323	0.339559	0.018*
C3	0.1465 (5)	0.4290 (4)	0.5109 (5)	0.0188 (10)
H3	0.138254	0.359887	0.548151	0.023*
C4	0.1833 (5)	0.5294 (4)	0.5812 (4)	0.0183 (10)
H4	0.197564	0.528274	0.665125	0.022*
C5	0.1988 (5)	0.6283 (4)	0.5295 (4)	0.0143 (9)
H5	0.224770	0.695960	0.577185	0.017*
C6	0.1880 (5)	0.7279 (4)	0.3425 (4)	0.0134 (9)
C7	0.4343 (5)	0.8524 (4)	0.4672 (5)	0.0162 (10)
C8	0.5220 (5)	0.8288 (4)	0.5882 (5)	0.0259 (12)
H8	0.488948	0.818120	0.648615	0.031*
C9	0.6579 (6)	0.8207 (5)	0.6214 (5)	0.0319 (13)
H9	0.717735	0.804495	0.704425	0.038*
C10	0.7062 (5)	0.8362 (4)	0.5339 (6)	0.0281 (13)
H10	0.799414	0.831392	0.556943	0.034*
C11	0.6195 (5)	0.8587 (5)	0.4130 (5)	0.0276 (12)
H11	0.653058	0.868078	0.352710	0.033*
C12	0.4828 (5)	0.8677 (5)	0.3788 (5)	0.0238 (11)
H12	0.423253	0.884189	0.295774	0.029*
Cl1	0.05719 (12)	0.32474 (9)	0.11352 (11)	0.0163 (2)
Cl2	0.5173 (17)	0.4244 (7)	0.6117 (12)	0.055 (2)	0.352 (3)
Cl3	0.4753 (18)	0.5382 (9)	0.3886 (13)	0.077 (3)	0.352 (3)
C13	0.5222 (19)	0.5578 (8)	0.5473 (13)	0.058 (4)	0.352 (3)
H13A	0.613356	0.590037	0.587480	0.069*	0.352 (3)
H13B	0.459970	0.611151	0.559777	0.069*	0.352 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0243 (3)	0.0133 (2)	0.0105 (2)	−0.0043 (2)	0.0078 (2)	−0.00122 (19)
Se2	0.0161 (2)	0.0113 (2)	0.0162 (2)	−0.00220 (19)	0.0076 (2)	−0.00216 (19)
N1	0.016 (2)	0.0113 (17)	0.014 (2)	−0.0002 (16)	0.0076 (17)	−0.0001 (16)
N2	0.023 (2)	0.0122 (18)	0.013 (2)	−0.0050 (17)	0.0073 (18)	0.0000 (16)
C1	0.013 (2)	0.012 (2)	0.012 (2)	−0.0013 (18)	0.0052 (19)	0.0001 (17)
C2	0.017 (2)	0.012 (2)	0.016 (2)	−0.0004 (19)	0.008 (2)	−0.0013 (19)
C3	0.018 (2)	0.018 (2)	0.021 (3)	0.000 (2)	0.009 (2)	0.005 (2)
C4	0.024 (3)	0.021 (2)	0.010 (2)	−0.002 (2)	0.008 (2)	−0.0019 (19)
C5	0.021 (2)	0.013 (2)	0.009 (2)	0.005 (2)	0.0062 (19)	−0.0008 (18)
C6	0.014 (2)	0.013 (2)	0.015 (2)	0.0005 (18)	0.007 (2)	0.0008 (18)
C7	0.015 (2)	0.009 (2)	0.022 (3)	−0.0017 (18)	0.005 (2)	−0.0016 (19)
C8	0.024 (3)	0.027 (3)	0.023 (3)	−0.003 (2)	0.008 (2)	−0.002 (2)
C9	0.019 (3)	0.032 (3)	0.029 (3)	0.001 (2)	−0.005 (2)	0.001 (3)
C10	0.014 (3)	0.016 (2)	0.049 (4)	0.000 (2)	0.008 (3)	−0.007 (2)
C11	0.025 (3)	0.028 (3)	0.034 (3)	−0.001 (2)	0.016 (3)	−0.003 (2)
C12	0.017 (3)	0.029 (3)	0.023 (3)	0.000 (2)	0.006 (2)	−0.002 (2)
Cl1	0.0179 (6)	0.0140 (5)	0.0172 (6)	−0.0004 (5)	0.0078 (5)	−0.0028 (4)
Cl2	0.043 (3)	0.040 (5)	0.088 (4)	−0.012 (4)	0.033 (3)	−0.019 (4)
Cl3	0.047 (4)	0.070 (7)	0.113 (5)	−0.004 (6)	0.035 (4)	−0.004 (6)
C13	0.036 (6)	0.049 (7)	0.096 (7)	−0.013 (7)	0.036 (6)	0.005 (7)

Geometric parameters (Å, º) top

Se1—N2	1.863 (4)	C7—C8	1.385 (7)
Se1—C1	1.877 (4)	C7—C12	1.390 (7)
Se2—C6	1.926 (5)	C8—C9	1.388 (7)
Se2—C7	1.946 (5)	C8—H8	0.9500
N1—C1	1.367 (6)	C9—C10	1.379 (8)
N1—C5	1.380 (6)	C9—H9	0.9500
N1—C6	1.435 (6)	C10—C11	1.380 (8)
N2—C6	1.285 (6)	C10—H10	0.9500
C1—C2	1.396 (6)	C11—C12	1.395 (7)
C2—C3	1.380 (6)	C11—H11	0.9500
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.405 (7)	Cl2—C13	1.7596 (12)
C3—H3	0.9500	Cl3—C13	1.7597 (11)
C4—C5	1.362 (6)	C13—H13A	0.9900
C4—H4	0.9500	C13—H13B	0.9900
C5—H5	0.9500

N2—Se1—C1	87.06 (18)	C8—C7—C12	119.8 (5)
C6—Se2—C7	96.45 (18)	C8—C7—Se2	118.9 (4)
C1—N1—C5	121.5 (4)	C12—C7—Se2	121.2 (4)
C1—N1—C6	114.4 (4)	C7—C8—C9	120.2 (5)
C5—N1—C6	124.2 (4)	C7—C8—H8	119.9
C6—N2—Se1	112.2 (3)	C9—C8—H8	119.9
N1—C1—C2	120.1 (4)	C10—C9—C8	120.0 (5)
N1—C1—Se1	109.7 (3)	C10—C9—H9	120.0
C2—C1—Se1	130.2 (3)	C8—C9—H9	120.0
C3—C2—C1	118.7 (4)	C9—C10—C11	120.1 (5)
C3—C2—H2	120.6	C9—C10—H10	119.9
C1—C2—H2	120.6	C11—C10—H10	119.9
C2—C3—C4	120.2 (4)	C10—C11—C12	120.3 (5)
C2—C3—H3	119.9	C10—C11—H11	119.9
C4—C3—H3	119.9	C12—C11—H11	119.9
C5—C4—C3	120.3 (4)	C7—C12—C11	119.5 (5)
C5—C4—H4	119.8	C7—C12—H12	120.2
C3—C4—H4	119.8	C11—C12—H12	120.2
C4—C5—N1	119.2 (4)	Cl2—C13—Cl3	107.9 (5)
C4—C5—H5	120.4	Cl2—C13—H13A	110.1
N1—C5—H5	120.4	Cl3—C13—H13A	110.1
N2—C6—N1	116.6 (4)	Cl2—C13—H13B	110.1
N2—C6—Se2	122.4 (3)	Cl3—C13—H13B	110.1
N1—C6—Se2	121.0 (3)	H13A—C13—H13B	108.4

C1—Se1—N2—C6	−0.4 (4)	Se1—N2—C6—N1	−0.5 (5)
C5—N1—C1—C2	−1.3 (7)	Se1—N2—C6—Se2	179.5 (2)
C6—N1—C1—C2	179.9 (4)	C1—N1—C6—N2	1.5 (6)
C5—N1—C1—Se1	177.1 (3)	C5—N1—C6—N2	−177.3 (4)
C6—N1—C1—Se1	−1.6 (5)	C1—N1—C6—Se2	−178.6 (3)
N2—Se1—C1—N1	1.1 (3)	C5—N1—C6—Se2	2.7 (6)
N2—Se1—C1—C2	179.4 (5)	C12—C7—C8—C9	0.1 (8)
N1—C1—C2—C3	0.4 (7)	Se2—C7—C8—C9	−176.7 (4)
Se1—C1—C2—C3	−177.7 (4)	C7—C8—C9—C10	0.0 (8)
C1—C2—C3—C4	1.1 (7)	C8—C9—C10—C11	−0.6 (8)
C2—C3—C4—C5	−1.7 (7)	C9—C10—C11—C12	1.0 (8)
C3—C4—C5—N1	0.8 (7)	C8—C7—C12—C11	0.3 (8)
C1—N1—C5—C4	0.7 (7)	Se2—C7—C12—C11	177.0 (4)
C6—N1—C5—C4	179.4 (4)	C10—C11—C12—C7	−0.8 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1	0.95	2.60	3.297 (5)	131
C3—H3···Cl1ⁱ	0.95	2.60	3.526 (5)	167
C5—H5···Se2	0.95	2.82	3.242 (5)	108
C5—H5···N2ⁱⁱ	0.95	2.45	3.179 (6)	134

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+3/2, z+1/2.

Funding information

This work was performed under the support of the Russian Science Foundation (award No. 22–73–10007).

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