The reaction between 2-pyridylselenenyl chloride and isobutyronitrile results in the formation of the corresponding cationic pyridinium-fused 1,2,4-selenodiazole, namely, 3-(propan-2-yl)-1,2,4-[1,2,4]selenadiazolo[4,5-a]pyridin-4-ylium chloride, C9H11N2Se+·Cl−, in high yield (89%). The bifurcated Se⋯Cl−⋯H—Cl chalcogen-hydrogen-bonding interactions were analysed by DFT followed by a topological analysis of the electron-density distribution.
Keywords: crystal structure; chalcogen-hydrogen bonding; 1,2,4-selenodiazole
Abstract
The reaction between 2-pyridylselenenyl chloride and isobutyronitrile results in the formation of the corresponding cationic pyridinium-fused 1,2,4-selenodiazole, namely, 3-(propan-2-yl)-1,2,4-[1,2,4]selenadiazolo[4,5-a]pyridin-4-ylium chloride, C9H11N2Se+·Cl−, in high yield (89%). The structure of the compound, established by means of single-crystal X-ray analysis at 100 K, has monoclinic (P21/c) symmetry and revealed the presence of bifurcated chalcogen-hydrogen bonding Se⋯Cl−⋯H—Cl, and these non-covalent contacts were analysed by DFT calculations followed by a topological analysis of the electron-density distribution (ωB97XD/6-311++G** level of theory).
1. Chemical context
Recently, we discovered a novel cycloaddition reaction between nitriles and 2-pyridylselenyl reagents (Artemjev et al., 2023 ▸; Khrustalev et al., 2021 ▸). Importantly, the reaction proceeds under mild conditions with high chemoselectivity and results in the formation of pyridinium-fused selenodiazolium salts in high yields. The Se centre in these systems acts as a chalcogen bond donor and provides two σ-holes (Grudova et al., 2022a
▸,b
▸). The 1,2,4-selenodiazolium salts were shown to form supramolecular dimers via four-center Se⋯X (X = Hal, N) chalcogen-bonding interactions (Grudova et al., 2022a
▸,b
▸). In some instances, other types of supramolecular organization were observed, depending on the nitrile employed in the cycloaddition reaction (Grudova et al., 2022a
▸,b
▸; Sapronov et al., 2022 ▸, 2023 ▸; Artemjev et al., 2022 ▸; Buslov et al., 2021 ▸).
Here we report the preparation and structural characterization of a cationic pyridinium-fused 1,2,4-selenodiazole, which was prepared via reaction of 2-pyridylselenenyl chloride with isobutyronitrile (reagent ratio of 1:1). The reaction was carried out under stirring at room temperature in CH2Cl2/Et2O over 24 h, which led to the formation of a white suspension. Isolation and purification gave a crystalline solid of the target compound in a yield of 89%.
2. Structural commentary
The title compound (Fig. 1 ▸) crystallized in space group P21/c with four cations and four Cl− anions in the asymmetric unit. The four cations exhibit identical bond distances and angles, except for the dihedral angle of the isopropyl substituent [N—C—C—C torsion angles are in the range −15.9 (12) to 17.7 (11)°]. The 1,2,4-selenodiazole fragments are almost planar (r.m.s.d. = 0.008–0.014 Å). The Se⋯Cl distances lie in the range 2.901 (3) – 2.956 (3) Å.
Figure 1.
Molecular structure of one of the four conformational isomers in the title compound.
Interestingly, the novel 1,2,4-selenodiazole did not form supramolecular dimers via Se⋯N contacts.
3. Supramolecular features and QTAIM analysis
The crystal packing is shown in Fig. 2 ▸. The molecules of the title compound are packed in layers parallel to the ac plane. Each row of 1,2,4-selenodiazolium salts in the layer is located antiparallel to the adjacent one. In addition to Se⋯Cl− contacts (Table 1 ▸), the anions form C—H⋯Cl− contacts (Table 2 ▸) that link the cations and anions both within the layers and between them.
Figure 2.
View along the a axis of the crystal packing of the title compound.
Table 1. Selected interatomic distances (Å).
| Se1⋯Cl1 | 2.957 (4) | Se3⋯Cl3 | 2.934 (4) |
| Se1⋯N1 | 2.656 (8) | Se3⋯N5 | 2.661 (8) |
| Se2⋯Cl2 | 2.900 (4) | Se4⋯Cl4 | 2.920 (4) |
| Se2⋯N3 | 2.664 (7) | Se4⋯N7 | 2.658 (8) |
Table 2. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C2—H2⋯Cl1 | 0.95 | 2.62 | 3.327 (10) | 132 |
| C3—H3⋯Cl2i | 0.95 | 2.67 | 3.598 (9) | 167 |
| C5—H5⋯Cl1ii | 0.95 | 2.67 | 3.395 (10) | 133 |
| C11—H11⋯Cl2 | 0.95 | 2.61 | 3.288 (10) | 129 |
| C14—H14⋯Cl2ii | 0.95 | 2.47 | 3.310 (10) | 147 |
| C18—H18C⋯Cl4iii | 0.98 | 2.73 | 3.687 (11) | 167 |
| C20—H20⋯Cl3 | 0.95 | 2.67 | 3.364 (10) | 131 |
| C23—H23⋯Cl3iv | 0.95 | 2.73 | 3.418 (10) | 130 |
| C29—H29⋯Cl4 | 0.95 | 2.63 | 3.323 (10) | 130 |
| C30—H30⋯Cl3v | 0.95 | 2.81 | 3.651 (9) | 148 |
| C32—H32⋯Cl4ii | 0.95 | 2.76 | 3.452 (9) | 131 |
Symmetry codes: (i)
; (ii)
; (iii)
; (iv)
; (v)
.
A Hirshfeld surface analysis was performed to investigate which interatomic contacts make the largest contributions to the crystal packing. Fig. 3 ▸ shows the Hirshfeld surface mapped over d norm where the region of the short intermolecular Se⋯Cl contact is indicated by an intense red spot. The contributions of the different interatomic contacts to the Hirshfeld surface are H⋯H (47.0%), Se⋯H (10.5%), Cl⋯H (10.4%), C⋯H (10.1%), N⋯H (8.5%), Se⋯C (4.5%), Se⋯Cl (2.7%), Cl⋯C (1.8%), Se⋯N (1.6%), Cl⋯N (1.3%), N⋯C (1.0%), N⋯N (0.5%), and C⋯C (0.1%). Thus, the Hirshfeld surface analysis for the crystal structure reveals that crystal packing is determined primarily by intermolecular contacts involving hydrogen atoms.
Figure 3.
Total Hirshfeld surface mapped over d norm and delineated into Se⋯H, Cl⋯H, C⋯H and N⋯H interactions.
Interestingly, the title compound did not form supramolecular dimers via Se⋯N contacts. To obtain a deeper understanding of the nature and quantify the strength of the bifurcated Se⋯Cl−⋯H—C chalcogen-hydrogen bonding in the title compound, single-point DFT calculations based on the experimental X-ray geometry were performed at the B97XD/6-311++G** level of theory using the dispersion-corrected hybrid functional ωB97XD using GAUSSIAN09 (Frisch et al., 2009 ▸) with the 6-311++G** basis sets used for all atoms, followed by a topological analysis of the electron-density distribution.
A QTAIM analysis of the model structure demonstrates the presence of bond critical points (3, −1) for short contacts Se⋯Cl− and C—H⋯Cl− in the formed 1,2,4-selenodiazole (Table 3 ▸ and Fig. 4 ▸). The low magnitude of the electron density, positive values of the Laplacian of the electron density and zero or very close to zero values of energy density in these bond critical points (3, −1) and estimated strength for appropriate short contacts are typical for weak, purely non-covalent interactions (Espinosa et al., 2002 ▸). Note that the nature of the discussed non-covalent contacts are similar to those weak interactions in closely related chemical systems (Grudova et al., 2022a ▸,b ▸).
Table 3. Values of the density of all electrons ρ(r), Laplacian of electron density ∇2ρ(r) and appropriate λ2 eigenvalues, energy density – H b, potential energy density – V(r), Lagrangian kinetic energy – G(r), and electron localization function – ELF (a.u.) at the bond critical points (3, −1), corresponding to bifurcated chalcogen-hydrogen bonding Se⋯Cl−⋯H—C in the structure, and estimated strength for these interactions E int ≃ –V(r)/2 (kcal mol−1).
The Bondi (1966 ▸) van der Waals radii for the H, Se, and Cl atoms are 1.20, 1.90, and 1.75 Å, respectively.
| Contact (Å) | ρ(r) | ∇2ρ(r) | λ2 | H b | V(r) | G(r) | ELF | E int |
|---|---|---|---|---|---|---|---|---|
| Se⋯Cl− 2.900 | 0.027 | 0.060 | −0.027 | 0.000 | −0.015 | 0.015 | 0.170 | 4.7 |
| C–H⋯Cl− 2.609 | 0.012 | 0.043 | −0.012 | 0.002 | −0.006 | 0.008 | 0.045 | 1.9 |
| Se⋯Cl− 2.957 | 0.024 | 0.056 | −0.024 | 0.001 | −0.013 | 0.014 | 0.142 | 4.1 |
| C–H⋯Cl− 2.617 | 0.012 | 0.041 | −0.012 | 0.002 | −0.006 | 0.008 | 0.045 | 1.9 |
| Se⋯Cl− 2.934 | 0.025 | 0.058 | −0.025 | 0.000 | −0.014 | 0.014 | 0.147 | 4.4 |
| C–H⋯Cl− 2.667 | 0.011 | 0.037 | −0.011 | 0.002 | −0.005 | 0.007 | 0.041 | 1.6 |
| Se⋯Cl− 2.920 | 0.026 | 0.058 | −0.026 | 0.000 | −0.015 | 0.015 | 0.165 | 4.7 |
| C–H⋯Cl− 2.633 | 0.012 | 0.040 | −0.012 | 0.002 | −0.006 | 0.008 | 0.044 | 1.9 |
Figure 4.
Contour line diagram of the Laplacian of electron density distribution ∇2r(r), bond paths, and selected zero-flux surfaces (left panel), visualization of electron localization function (ELF, center panel) and reduced density gradient (RDG, right panel) analyses for bifurcated chalcogen-hydrogen bonding Se⋯Cl−⋯H–C in sample (for Se⋯Cl− 2.900 Å and C–H⋯Cl− 2.609 Å). 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 are Å and the colour scale for the ELF and RDG maps is presented in a.u.
4. Database survey
A search in the Cambridge Structural Database (CSD, Version 5.43, update of Sep. 2022; Groom et al., 2016 ▸) gave only 16 hits for 1,2,4-selenodiazolium salts. These salts 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 CF3COO− anion (YEJXEU; Artemjev et al., 2022 ▸), AuCl4 − (YEJXUK; Artemjev et al., 2022 ▸), ReO4 − (YEJYAR; Artemjev et al., 2022 ▸).
5. Synthesis and crystallization
General remarks. All manipulations were carried out in air and all 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 immediately prior to use. NMR spectra were recorded on a Bruker Avance III (1H: 400 MHz); chemical shifts (δ) are given in ppm, coupling constants (J) in Hz. 2-Pyridylselenyl chloride was synthesized by our method (Artemjev et al., 2023 ▸; Khrustalev et al., 2021 ▸). Isobutyronitrile (81 µmol, 5.6 mg) was added to a suspension of 2-pyridylselenyl chloride (81 µmol, 15.5 mg) in CH2Cl2/Et2O (1/1, 4 mL), and the mixture was stirred at room temperature for 24 h. The formed colorless precipitate was filtered, washed with Et2O (3 × 1 mL) and dried under vacuum. Yield 18.8 mg (89%), colorless blocks. 1H NMR (400 MHz, chloroform-d) δ 8.48 (d, J = 4.8 Hz, 1H), 7.83 (d, J = 7.9 Hz, 1H), 7.58 (td, J = 7.8 Hz, 1H), 7.12 (td, J = 7.5 Hz, 1H), 2.70 (hept, J = 7.0 Hz, 1H), 1.33 (d, J = 7.0 Hz, 6H). Crystals suitable for X-ray analysis were obtained by the slow evaporation of a CH2Cl2 solution.
6. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 4 ▸. H atoms were positioned geometrically (C—H = 0.95–1.00 Å) and refined as riding with U iso(H) = 1.2–1.5U eq(C). The remaining positive and negative residual electron density close to the Se1, Se2, Se3 and Se4 atom positions (1.71 Å−3 at 0.94 Å from Se4, 1.67 Å−3 at 1.05 Å from Se2, 1.58 Å−3 at 1.03 Å from Se3, 1.54 Å−3 at 1.06 Å from Se4 and −1.53 Å−3 at 1.06 Å from Se4) suggests the possible presence of a small twin component as well.
Table 4. Experimental details.
| Crystal data | |
| Chemical formula | C9H11N2Se+·Cl− |
| M r | 261.61 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 100 |
| a, b, c (Å) | 9.054 (11), 15.015 (15), 30.93 (3) |
| β (°) | 94.10 (3) |
| V (Å3) | 4194 (8) |
| Z | 16 |
| Radiation type | Mo Kα |
| μ (mm−1) | 3.79 |
| Crystal size (mm) | 0.2 × 0.2 × 0.1 |
| Data collection | |
| Diffractometer | Bruker D8 Venture |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| T min, T max | 0.499, 0.746 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 25216, 9604, 6328 |
| R int | 0.092 |
| (sin θ/λ)max (Å−1) | 0.650 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.080, 0.192, 1.10 |
| No. of reflections | 9604 |
| No. of parameters | 477 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 1.77, −1.49 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989024000938/ex2079sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989024000938/ex2079Isup2.hkl
Fingerprint plots. DOI: 10.1107/S2056989024000938/ex2079sup3.zip
CCDC reference: 2328546
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
Authors’ contributions are as follows: conceptualization, AWT, AGT; methodology, AAS, AGT; validation: AWT, ASK, AGT; formal analysis: ASN, TAL; investigation: AWT, ASK, TAL and AGT; resources, ASK, AGT; data curation, AAS, ASN, AKK; writing (original draft), ASN, AWT and TAL; writing (review and editing), AAS, AGT, TAL; visualization, AWT, TAL; supervision, AWT, AGT; project administration, AGT; funding acquisition, AGT, TAL.
supplementary crystallographic information
Crystal data
| C9H11N2Se+·Cl− | F(000) = 2080 |
| Mr = 261.61 | Dx = 1.657 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.054 (11) Å | Cell parameters from 5157 reflections |
| b = 15.015 (15) Å | θ = 2.5–27.0° |
| c = 30.93 (3) Å | µ = 3.79 mm−1 |
| β = 94.10 (3)° | T = 100 K |
| V = 4194 (8) Å3 | Block, colourless |
| Z = 16 | 0.2 × 0.2 × 0.1 mm |
Data collection
| Bruker D8 Venture diffractometer | 6328 reflections with I > 2σ(I) |
| φ and ω scans | Rint = 0.092 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 27.5°, θmin = 1.5° |
| Tmin = 0.499, Tmax = 0.746 | h = −11→10 |
| 25216 measured reflections | k = −17→19 |
| 9604 independent reflections | l = −34→40 |
Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.080 | H-atom parameters constrained |
| wR(F2) = 0.192 | w = 1/[σ2(Fo2) + (0.0572P)2 + 24.4862P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.10 | (Δ/σ)max < 0.001 |
| 9604 reflections | Δρmax = 1.77 e Å−3 |
| 477 parameters | Δρmin = −1.49 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Se1 | 0.47831 (10) | 0.56571 (5) | 0.44129 (3) | 0.0188 (2) | |
| N1 | 0.2029 (8) | 0.5041 (4) | 0.4321 (2) | 0.0158 (14) | |
| N2 | 0.3169 (8) | 0.6405 (4) | 0.4298 (2) | 0.0208 (15) | |
| C1 | 0.3415 (9) | 0.4706 (5) | 0.4407 (2) | 0.0157 (16) | |
| C2 | 0.3662 (10) | 0.3806 (5) | 0.4468 (2) | 0.0215 (19) | |
| H2 | 0.463568 | 0.358285 | 0.452949 | 0.026* | |
| C3 | 0.2475 (10) | 0.3244 (5) | 0.4437 (3) | 0.0225 (19) | |
| H3 | 0.262519 | 0.262247 | 0.447472 | 0.027* | |
| C4 | 0.1014 (10) | 0.3578 (5) | 0.4348 (3) | 0.0231 (19) | |
| H4 | 0.019521 | 0.318133 | 0.432535 | 0.028* | |
| C5 | 0.0794 (10) | 0.4484 (5) | 0.4294 (3) | 0.0226 (18) | |
| H5 | −0.017461 | 0.472085 | 0.423951 | 0.027* | |
| C6 | 0.1954 (10) | 0.5998 (5) | 0.4265 (3) | 0.0182 (17) | |
| C7 | 0.0449 (10) | 0.6424 (5) | 0.4148 (3) | 0.0228 (19) | |
| H7 | −0.006834 | 0.606091 | 0.391248 | 0.027* | |
| C8 | −0.0552 (10) | 0.6457 (6) | 0.4531 (3) | 0.029 (2) | |
| H8A | −0.059140 | 0.586592 | 0.466403 | 0.043* | |
| H8B | −0.155223 | 0.664066 | 0.442583 | 0.043* | |
| H8C | −0.014747 | 0.688650 | 0.474718 | 0.043* | |
| C9 | 0.0689 (12) | 0.7371 (6) | 0.3968 (3) | 0.037 (2) | |
| H9A | 0.112941 | 0.775243 | 0.420018 | 0.055* | |
| H9B | −0.026482 | 0.762078 | 0.385810 | 0.055* | |
| H9C | 0.135472 | 0.733964 | 0.373246 | 0.055* | |
| Se2 | 0.99777 (10) | 0.98507 (5) | 0.43039 (3) | 0.0206 (2) | |
| N3 | 0.7271 (7) | 1.0382 (4) | 0.4473 (2) | 0.0155 (14) | |
| N4 | 0.8305 (9) | 0.9161 (4) | 0.4154 (2) | 0.0240 (16) | |
| C10 | 0.8686 (10) | 1.0696 (5) | 0.4521 (2) | 0.0201 (17) | |
| C11 | 0.9007 (10) | 1.1530 (5) | 0.4712 (3) | 0.0224 (18) | |
| H11 | 0.999354 | 1.174702 | 0.474969 | 0.027* | |
| C12 | 0.7821 (10) | 1.2025 (5) | 0.4842 (3) | 0.0223 (18) | |
| H12 | 0.799270 | 1.260398 | 0.495885 | 0.027* | |
| C13 | 0.6357 (10) | 1.1680 (5) | 0.4805 (3) | 0.0204 (18) | |
| H13 | 0.556089 | 1.201547 | 0.490621 | 0.024* | |
| C14 | 0.6109 (10) | 1.0862 (5) | 0.4623 (3) | 0.0217 (18) | |
| H14 | 0.513573 | 1.062152 | 0.459912 | 0.026* | |
| C15 | 0.7132 (10) | 0.9517 (5) | 0.4276 (3) | 0.0217 (18) | |
| C16 | 0.5614 (10) | 0.9090 (5) | 0.4235 (3) | 0.0244 (19) | |
| H16 | 0.515032 | 0.917789 | 0.451551 | 0.029* | |
| C17 | 0.5773 (12) | 0.8075 (6) | 0.4161 (4) | 0.043 (3) | |
| H17A | 0.631217 | 0.797054 | 0.390244 | 0.065* | |
| H17B | 0.478756 | 0.780391 | 0.412147 | 0.065* | |
| H17C | 0.631904 | 0.780693 | 0.441382 | 0.065* | |
| C18 | 0.4603 (12) | 0.9510 (6) | 0.3879 (3) | 0.034 (2) | |
| H18A | 0.468793 | 1.015964 | 0.389582 | 0.051* | |
| H18B | 0.357698 | 0.933378 | 0.391448 | 0.051* | |
| H18C | 0.489245 | 0.930671 | 0.359565 | 0.051* | |
| Se3 | 0.26260 (10) | 0.42116 (5) | 0.32555 (3) | 0.01773 (19) | |
| N5 | 0.5420 (8) | 0.4775 (4) | 0.3319 (2) | 0.0199 (15) | |
| N6 | 0.4195 (9) | 0.3446 (4) | 0.3392 (2) | 0.0226 (16) | |
| C19 | 0.4032 (9) | 0.5118 (5) | 0.3232 (3) | 0.0178 (16) | |
| C20 | 0.3850 (10) | 0.6028 (5) | 0.3142 (3) | 0.0198 (17) | |
| H20 | 0.288959 | 0.626641 | 0.307443 | 0.024* | |
| C21 | 0.5068 (10) | 0.6569 (5) | 0.3152 (3) | 0.0232 (19) | |
| H21 | 0.495070 | 0.718889 | 0.309785 | 0.028* | |
| C22 | 0.6498 (11) | 0.6212 (6) | 0.3244 (3) | 0.027 (2) | |
| H22 | 0.734293 | 0.658728 | 0.324740 | 0.033* | |
| C23 | 0.6658 (10) | 0.5327 (5) | 0.3327 (3) | 0.0218 (18) | |
| H23 | 0.761829 | 0.508431 | 0.339056 | 0.026* | |
| C24 | 0.5435 (10) | 0.3829 (5) | 0.3405 (3) | 0.0193 (17) | |
| C25 | 0.6916 (10) | 0.3370 (6) | 0.3495 (3) | 0.026 (2) | |
| H25 | 0.754221 | 0.373184 | 0.370862 | 0.031* | |
| C26 | 0.7723 (11) | 0.3267 (6) | 0.3083 (3) | 0.030 (2) | |
| H26A | 0.707544 | 0.296467 | 0.286124 | 0.045* | |
| H26B | 0.862308 | 0.291312 | 0.314442 | 0.045* | |
| H26C | 0.798948 | 0.385609 | 0.297642 | 0.045* | |
| C27 | 0.6644 (12) | 0.2436 (6) | 0.3695 (3) | 0.034 (2) | |
| H27A | 0.595387 | 0.209768 | 0.349877 | 0.050* | |
| H27B | 0.622106 | 0.250876 | 0.397530 | 0.050* | |
| H27C | 0.758506 | 0.211384 | 0.373494 | 0.050* | |
| Se4 | 1.25396 (10) | 0.52189 (5) | 0.20254 (3) | 0.0204 (2) | |
| N7 | 0.9756 (8) | 0.4644 (4) | 0.1977 (2) | 0.0195 (15) | |
| N8 | 1.0966 (8) | 0.5971 (4) | 0.1871 (2) | 0.0213 (15) | |
| C28 | 1.1139 (9) | 0.4318 (5) | 0.2066 (3) | 0.0187 (17) | |
| C29 | 1.1317 (10) | 0.3407 (5) | 0.2175 (3) | 0.0226 (19) | |
| H29 | 1.227441 | 0.316755 | 0.224650 | 0.027* | |
| C30 | 1.0089 (11) | 0.2875 (5) | 0.2175 (3) | 0.025 (2) | |
| H30 | 1.020121 | 0.225748 | 0.223666 | 0.030* | |
| C31 | 0.8675 (10) | 0.3229 (6) | 0.2085 (3) | 0.0253 (19) | |
| H31 | 0.782837 | 0.285610 | 0.209118 | 0.030* | |
| C32 | 0.8512 (9) | 0.4109 (5) | 0.1990 (3) | 0.0201 (17) | |
| H32 | 0.755249 | 0.435634 | 0.193195 | 0.024* | |
| C33 | 0.9714 (10) | 0.5569 (5) | 0.1863 (2) | 0.0205 (18) | |
| C34 | 0.8239 (10) | 0.6012 (5) | 0.1729 (3) | 0.0220 (18) | |
| H34 | 0.766938 | 0.559546 | 0.152766 | 0.026* | |
| C35 | 0.7292 (10) | 0.6186 (6) | 0.2117 (3) | 0.027 (2) | |
| H35A | 0.783686 | 0.657512 | 0.232708 | 0.040* | |
| H35B | 0.707740 | 0.561863 | 0.225694 | 0.040* | |
| H35C | 0.636091 | 0.647310 | 0.201416 | 0.040* | |
| C36 | 0.8505 (10) | 0.6869 (5) | 0.1477 (3) | 0.028 (2) | |
| H36A | 0.755127 | 0.712260 | 0.136934 | 0.042* | |
| H36B | 0.909601 | 0.673383 | 0.123245 | 0.042* | |
| H36C | 0.903625 | 0.729918 | 0.166944 | 0.042* | |
| Cl1 | 0.7227 (2) | 0.43621 (13) | 0.45609 (7) | 0.0235 (4) | |
| Cl2 | 1.2466 (2) | 1.08940 (12) | 0.46641 (7) | 0.0237 (4) | |
| Cl3 | 0.0233 (2) | 0.54927 (12) | 0.30482 (7) | 0.0218 (4) | |
| Cl4 | 1.4889 (2) | 0.39388 (13) | 0.22603 (7) | 0.0227 (4) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Se1 | 0.0212 (5) | 0.0144 (4) | 0.0206 (4) | −0.0026 (3) | −0.0009 (3) | −0.0022 (3) |
| N1 | 0.020 (4) | 0.016 (3) | 0.011 (3) | 0.000 (3) | −0.001 (3) | −0.002 (2) |
| N2 | 0.030 (4) | 0.016 (3) | 0.016 (4) | 0.000 (3) | −0.003 (3) | −0.005 (3) |
| C1 | 0.017 (4) | 0.019 (4) | 0.010 (4) | −0.003 (3) | 0.000 (3) | −0.003 (3) |
| C2 | 0.033 (5) | 0.019 (4) | 0.012 (4) | 0.000 (4) | −0.004 (4) | 0.001 (3) |
| C3 | 0.031 (5) | 0.018 (4) | 0.018 (4) | −0.008 (4) | 0.001 (4) | −0.003 (3) |
| C4 | 0.025 (5) | 0.019 (4) | 0.025 (5) | −0.003 (4) | −0.001 (4) | −0.003 (3) |
| C5 | 0.018 (5) | 0.029 (4) | 0.020 (4) | −0.001 (4) | −0.001 (3) | −0.002 (3) |
| C6 | 0.024 (5) | 0.011 (3) | 0.019 (4) | 0.003 (3) | −0.003 (3) | −0.001 (3) |
| C7 | 0.022 (5) | 0.025 (4) | 0.020 (4) | 0.008 (4) | −0.004 (4) | 0.001 (3) |
| C8 | 0.023 (5) | 0.025 (4) | 0.039 (6) | 0.002 (4) | 0.009 (4) | −0.005 (4) |
| C9 | 0.042 (7) | 0.036 (5) | 0.032 (6) | 0.015 (5) | 0.001 (5) | 0.007 (4) |
| Se2 | 0.0193 (5) | 0.0179 (4) | 0.0244 (5) | 0.0017 (3) | −0.0002 (3) | −0.0009 (3) |
| N3 | 0.013 (3) | 0.016 (3) | 0.018 (4) | 0.004 (3) | −0.001 (3) | −0.002 (2) |
| N4 | 0.030 (4) | 0.019 (3) | 0.023 (4) | 0.003 (3) | −0.003 (3) | −0.003 (3) |
| C10 | 0.027 (5) | 0.022 (4) | 0.010 (4) | 0.001 (4) | −0.004 (3) | 0.004 (3) |
| C11 | 0.026 (5) | 0.023 (4) | 0.018 (4) | −0.007 (4) | −0.006 (4) | 0.002 (3) |
| C12 | 0.023 (5) | 0.020 (4) | 0.023 (5) | −0.001 (4) | 0.000 (4) | 0.000 (3) |
| C13 | 0.020 (5) | 0.021 (4) | 0.021 (4) | 0.006 (3) | 0.000 (3) | −0.001 (3) |
| C14 | 0.018 (4) | 0.018 (4) | 0.029 (5) | 0.002 (3) | 0.001 (4) | 0.003 (3) |
| C15 | 0.032 (5) | 0.017 (4) | 0.015 (4) | −0.002 (4) | −0.007 (4) | 0.002 (3) |
| C16 | 0.021 (5) | 0.026 (4) | 0.025 (5) | −0.005 (4) | 0.001 (4) | −0.001 (3) |
| C17 | 0.039 (7) | 0.032 (5) | 0.058 (8) | −0.010 (5) | −0.003 (5) | −0.009 (5) |
| C18 | 0.038 (6) | 0.041 (5) | 0.022 (5) | −0.005 (5) | −0.006 (4) | −0.007 (4) |
| Se3 | 0.0200 (4) | 0.0133 (4) | 0.0197 (4) | −0.0013 (3) | −0.0001 (3) | −0.0003 (3) |
| N5 | 0.021 (4) | 0.023 (3) | 0.016 (4) | 0.002 (3) | −0.002 (3) | −0.003 (3) |
| N6 | 0.032 (5) | 0.016 (3) | 0.020 (4) | 0.000 (3) | 0.002 (3) | 0.001 (3) |
| C19 | 0.018 (4) | 0.017 (4) | 0.019 (4) | 0.005 (3) | 0.003 (3) | 0.000 (3) |
| C20 | 0.024 (5) | 0.013 (4) | 0.023 (4) | 0.001 (3) | −0.001 (3) | 0.000 (3) |
| C21 | 0.025 (5) | 0.014 (4) | 0.030 (5) | 0.001 (3) | −0.002 (4) | −0.001 (3) |
| C22 | 0.029 (5) | 0.025 (4) | 0.028 (5) | −0.010 (4) | −0.001 (4) | −0.001 (4) |
| C23 | 0.015 (4) | 0.024 (4) | 0.027 (5) | 0.000 (3) | 0.001 (3) | −0.002 (3) |
| C24 | 0.027 (5) | 0.015 (4) | 0.016 (4) | 0.005 (3) | −0.003 (3) | −0.001 (3) |
| C25 | 0.023 (5) | 0.026 (4) | 0.028 (5) | 0.002 (4) | −0.004 (4) | 0.003 (3) |
| C26 | 0.027 (6) | 0.032 (5) | 0.031 (5) | 0.011 (4) | 0.003 (4) | −0.002 (4) |
| C27 | 0.039 (6) | 0.026 (5) | 0.035 (6) | 0.010 (4) | 0.004 (5) | 0.009 (4) |
| Se4 | 0.0192 (5) | 0.0170 (4) | 0.0246 (5) | −0.0007 (3) | −0.0022 (3) | 0.0011 (3) |
| N7 | 0.024 (4) | 0.015 (3) | 0.018 (4) | −0.003 (3) | −0.003 (3) | −0.003 (3) |
| N8 | 0.018 (4) | 0.015 (3) | 0.031 (4) | 0.005 (3) | 0.000 (3) | 0.007 (3) |
| C28 | 0.019 (4) | 0.019 (4) | 0.018 (4) | 0.001 (3) | −0.003 (3) | −0.005 (3) |
| C29 | 0.024 (5) | 0.018 (4) | 0.023 (5) | 0.003 (3) | −0.011 (4) | 0.000 (3) |
| C30 | 0.034 (6) | 0.019 (4) | 0.022 (5) | 0.003 (4) | −0.007 (4) | 0.001 (3) |
| C31 | 0.021 (5) | 0.026 (4) | 0.028 (5) | −0.009 (4) | −0.001 (4) | −0.004 (3) |
| C32 | 0.013 (4) | 0.025 (4) | 0.023 (5) | 0.000 (3) | −0.001 (3) | −0.006 (3) |
| C33 | 0.036 (5) | 0.012 (4) | 0.012 (4) | −0.007 (3) | −0.002 (4) | 0.002 (3) |
| C34 | 0.025 (5) | 0.023 (4) | 0.016 (4) | 0.003 (4) | −0.007 (4) | −0.001 (3) |
| C35 | 0.022 (5) | 0.024 (4) | 0.034 (5) | 0.004 (4) | 0.000 (4) | −0.004 (4) |
| C36 | 0.026 (5) | 0.018 (4) | 0.038 (6) | 0.008 (4) | −0.008 (4) | 0.004 (3) |
| Cl1 | 0.0217 (11) | 0.0213 (10) | 0.0273 (11) | 0.0000 (8) | 0.0012 (8) | −0.0019 (8) |
| Cl2 | 0.0184 (11) | 0.0191 (9) | 0.0332 (12) | 0.0000 (8) | −0.0020 (9) | 0.0056 (8) |
| Cl3 | 0.0191 (11) | 0.0183 (9) | 0.0278 (11) | 0.0021 (8) | −0.0001 (8) | −0.0026 (7) |
| Cl4 | 0.0197 (11) | 0.0264 (10) | 0.0216 (11) | 0.0025 (8) | −0.0005 (8) | 0.0008 (8) |
Geometric parameters (Å, º)
| Se1—N2 | 1.857 (7) | Se3—N6 | 1.853 (7) |
| Se1—C1 | 1.890 (8) | Se3—C19 | 1.868 (8) |
| N1—C1 | 1.360 (10) | N5—C19 | 1.367 (10) |
| N1—C5 | 1.394 (10) | N5—C23 | 1.393 (11) |
| N1—C6 | 1.448 (9) | N5—C24 | 1.444 (10) |
| N2—C6 | 1.256 (11) | N6—C24 | 1.260 (11) |
| C1—C2 | 1.381 (11) | C19—C20 | 1.402 (10) |
| C2—H2 | 0.9500 | C20—H20 | 0.9500 |
| C2—C3 | 1.364 (12) | C20—C21 | 1.369 (12) |
| C3—H3 | 0.9500 | C21—H21 | 0.9500 |
| C3—C4 | 1.422 (12) | C21—C22 | 1.411 (12) |
| C4—H4 | 0.9500 | C22—H22 | 0.9500 |
| C4—C5 | 1.383 (11) | C22—C23 | 1.359 (11) |
| C5—H5 | 0.9500 | C23—H23 | 0.9500 |
| C6—C7 | 1.526 (11) | C24—C25 | 1.516 (12) |
| C7—H7 | 1.0000 | C25—H25 | 1.0000 |
| C7—C8 | 1.542 (12) | C25—C26 | 1.523 (12) |
| C7—C9 | 1.549 (12) | C25—C27 | 1.559 (12) |
| C8—H8A | 0.9800 | C26—H26A | 0.9800 |
| C8—H8B | 0.9800 | C26—H26B | 0.9800 |
| C8—H8C | 0.9800 | C26—H26C | 0.9800 |
| C9—H9A | 0.9800 | C27—H27A | 0.9800 |
| C9—H9B | 0.9800 | C27—H27B | 0.9800 |
| C9—H9C | 0.9800 | C27—H27C | 0.9800 |
| Se2—N4 | 1.866 (8) | Se4—N8 | 1.854 (7) |
| Se2—C10 | 1.882 (8) | Se4—C28 | 1.865 (8) |
| N3—C10 | 1.363 (11) | N7—C28 | 1.354 (11) |
| N3—C14 | 1.383 (10) | N7—C32 | 1.386 (10) |
| N3—C15 | 1.437 (10) | N7—C33 | 1.433 (9) |
| N4—C15 | 1.270 (11) | N8—C33 | 1.283 (11) |
| C10—C11 | 1.407 (11) | C28—C29 | 1.415 (11) |
| C11—H11 | 0.9500 | C29—H29 | 0.9500 |
| C11—C12 | 1.389 (12) | C29—C30 | 1.369 (12) |
| C12—H12 | 0.9500 | C30—H30 | 0.9500 |
| C12—C13 | 1.420 (12) | C30—C31 | 1.396 (12) |
| C13—H13 | 0.9500 | C31—H31 | 0.9500 |
| C13—C14 | 1.364 (11) | C31—C32 | 1.361 (11) |
| C14—H14 | 0.9500 | C32—H32 | 0.9500 |
| C15—C16 | 1.513 (12) | C33—C34 | 1.522 (12) |
| C16—H16 | 1.0000 | C34—H34 | 1.0000 |
| C16—C17 | 1.550 (12) | C34—C35 | 1.546 (12) |
| C16—C18 | 1.518 (12) | C34—C36 | 1.533 (11) |
| C17—H17A | 0.9800 | C35—H35A | 0.9800 |
| C17—H17B | 0.9800 | C35—H35B | 0.9800 |
| C17—H17C | 0.9800 | C35—H35C | 0.9800 |
| C18—H18A | 0.9800 | C36—H36A | 0.9800 |
| C18—H18B | 0.9800 | C36—H36B | 0.9800 |
| C18—H18C | 0.9800 | C36—H36C | 0.9800 |
| Se1···Cl1 | 2.957 (4) | Se3···Cl3 | 2.934 (4) |
| Se1···N1 | 2.656 (8) | Se3···N5 | 2.661 (8) |
| Se2···Cl2 | 2.900 (4) | Se4···Cl4 | 2.920 (4) |
| Se2···N3 | 2.664 (7) | Se4···N7 | 2.658 (8) |
| N2—Se1—C1 | 87.0 (3) | N6—Se3—C19 | 87.0 (3) |
| C1—N1—C5 | 121.0 (7) | C19—N5—C23 | 120.4 (7) |
| C1—N1—C6 | 115.1 (7) | C19—N5—C24 | 113.8 (7) |
| C5—N1—C6 | 123.9 (7) | C23—N5—C24 | 125.8 (7) |
| C6—N2—Se1 | 113.2 (5) | C24—N6—Se3 | 113.0 (5) |
| N1—C1—Se1 | 108.5 (5) | N5—C19—Se3 | 109.7 (5) |
| N1—C1—C2 | 121.8 (7) | N5—C19—C20 | 120.0 (8) |
| C2—C1—Se1 | 129.7 (7) | C20—C19—Se3 | 130.3 (7) |
| C1—C2—H2 | 120.8 | C19—C20—H20 | 120.3 |
| C3—C2—C1 | 118.5 (8) | C21—C20—C19 | 119.4 (8) |
| C3—C2—H2 | 120.8 | C21—C20—H20 | 120.3 |
| C2—C3—H3 | 119.6 | C20—C21—H21 | 119.9 |
| C2—C3—C4 | 120.8 (8) | C20—C21—C22 | 120.3 (7) |
| C4—C3—H3 | 119.6 | C22—C21—H21 | 119.9 |
| C3—C4—H4 | 120.2 | C21—C22—H22 | 120.2 |
| C5—C4—C3 | 119.6 (8) | C23—C22—C21 | 119.6 (8) |
| C5—C4—H4 | 120.2 | C23—C22—H22 | 120.2 |
| N1—C5—H5 | 120.8 | N5—C23—H23 | 119.9 |
| C4—C5—N1 | 118.3 (8) | C22—C23—N5 | 120.2 (8) |
| C4—C5—H5 | 120.8 | C22—C23—H23 | 119.9 |
| N1—C6—C7 | 118.5 (7) | N5—C24—C25 | 118.5 (7) |
| N2—C6—N1 | 116.1 (7) | N6—C24—N5 | 116.5 (7) |
| N2—C6—C7 | 125.3 (7) | N6—C24—C25 | 124.9 (7) |
| C6—C7—H7 | 108.0 | C24—C25—H25 | 109.0 |
| C6—C7—C8 | 113.3 (7) | C24—C25—C26 | 111.3 (7) |
| C6—C7—C9 | 108.9 (7) | C24—C25—C27 | 108.6 (8) |
| C8—C7—H7 | 108.0 | C26—C25—H25 | 109.0 |
| C8—C7—C9 | 110.6 (7) | C26—C25—C27 | 109.8 (7) |
| C9—C7—H7 | 108.0 | C27—C25—H25 | 109.0 |
| C7—C8—H8A | 109.5 | C25—C26—H26A | 109.5 |
| C7—C8—H8B | 109.5 | C25—C26—H26B | 109.5 |
| C7—C8—H8C | 109.5 | C25—C26—H26C | 109.5 |
| H8A—C8—H8B | 109.5 | H26A—C26—H26B | 109.5 |
| H8A—C8—H8C | 109.5 | H26A—C26—H26C | 109.5 |
| H8B—C8—H8C | 109.5 | H26B—C26—H26C | 109.5 |
| C7—C9—H9A | 109.5 | C25—C27—H27A | 109.5 |
| C7—C9—H9B | 109.5 | C25—C27—H27B | 109.5 |
| C7—C9—H9C | 109.5 | C25—C27—H27C | 109.5 |
| H9A—C9—H9B | 109.5 | H27A—C27—H27B | 109.5 |
| H9A—C9—H9C | 109.5 | H27A—C27—H27C | 109.5 |
| H9B—C9—H9C | 109.5 | H27B—C27—H27C | 109.5 |
| N4—Se2—C10 | 87.0 (4) | N8—Se4—C28 | 86.9 (3) |
| C10—N3—C14 | 121.0 (7) | C28—N7—C32 | 121.7 (7) |
| C10—N3—C15 | 114.3 (7) | C28—N7—C33 | 114.2 (7) |
| C14—N3—C15 | 124.6 (7) | C32—N7—C33 | 124.1 (7) |
| C15—N4—Se2 | 112.0 (6) | C33—N8—Se4 | 112.3 (5) |
| N3—C10—Se2 | 109.3 (5) | N7—C28—Se4 | 110.3 (5) |
| N3—C10—C11 | 121.2 (8) | N7—C28—C29 | 119.1 (7) |
| C11—C10—Se2 | 129.4 (7) | C29—C28—Se4 | 130.6 (7) |
| C10—C11—H11 | 121.4 | C28—C29—H29 | 120.5 |
| C12—C11—C10 | 117.2 (8) | C30—C29—C28 | 119.1 (8) |
| C12—C11—H11 | 121.4 | C30—C29—H29 | 120.5 |
| C11—C12—H12 | 119.4 | C29—C30—H30 | 119.6 |
| C11—C12—C13 | 121.2 (8) | C29—C30—C31 | 120.7 (8) |
| C13—C12—H12 | 119.4 | C31—C30—H30 | 119.6 |
| C12—C13—H13 | 120.4 | C30—C31—H31 | 120.1 |
| C14—C13—C12 | 119.1 (8) | C32—C31—C30 | 119.8 (8) |
| C14—C13—H13 | 120.4 | C32—C31—H31 | 120.1 |
| N3—C14—H14 | 120.0 | N7—C32—H32 | 120.2 |
| C13—C14—N3 | 120.1 (8) | C31—C32—N7 | 119.6 (8) |
| C13—C14—H14 | 120.0 | C31—C32—H32 | 120.2 |
| N3—C15—C16 | 118.1 (7) | N7—C33—C34 | 119.8 (7) |
| N4—C15—N3 | 117.1 (8) | N8—C33—N7 | 116.3 (8) |
| N4—C15—C16 | 124.8 (7) | N8—C33—C34 | 123.8 (7) |
| C15—C16—H16 | 107.8 | C33—C34—H34 | 107.5 |
| C15—C16—C17 | 109.6 (8) | C33—C34—C35 | 112.8 (7) |
| C15—C16—C18 | 112.5 (7) | C33—C34—C36 | 109.8 (7) |
| C17—C16—H16 | 107.8 | C35—C34—H34 | 107.5 |
| C18—C16—H16 | 107.8 | C36—C34—H34 | 107.5 |
| C18—C16—C17 | 111.1 (8) | C36—C34—C35 | 111.6 (7) |
| C16—C17—H17A | 109.5 | C34—C35—H35A | 109.5 |
| C16—C17—H17B | 109.5 | C34—C35—H35B | 109.5 |
| C16—C17—H17C | 109.5 | C34—C35—H35C | 109.5 |
| H17A—C17—H17B | 109.5 | H35A—C35—H35B | 109.5 |
| H17A—C17—H17C | 109.5 | H35A—C35—H35C | 109.5 |
| H17B—C17—H17C | 109.5 | H35B—C35—H35C | 109.5 |
| C16—C18—H18A | 109.5 | C34—C36—H36A | 109.5 |
| C16—C18—H18B | 109.5 | C34—C36—H36B | 109.5 |
| C16—C18—H18C | 109.5 | C34—C36—H36C | 109.5 |
| H18A—C18—H18B | 109.5 | H36A—C36—H36B | 109.5 |
| H18A—C18—H18C | 109.5 | H36A—C36—H36C | 109.5 |
| H18B—C18—H18C | 109.5 | H36B—C36—H36C | 109.5 |
| Se1—N2—C6—N1 | −0.2 (9) | Se3—N6—C24—N5 | 0.9 (9) |
| Se1—N2—C6—C7 | −176.5 (6) | Se3—N6—C24—C25 | −178.1 (6) |
| Se1—C1—C2—C3 | −178.3 (6) | Se3—C19—C20—C21 | 178.7 (7) |
| N1—C1—C2—C3 | 0.3 (12) | N5—C19—C20—C21 | −1.4 (12) |
| N1—C6—C7—C8 | 74.0 (9) | N5—C24—C25—C26 | −73.8 (9) |
| N1—C6—C7—C9 | −162.4 (7) | N5—C24—C25—C27 | 165.2 (7) |
| N2—Se1—C1—N1 | 0.8 (5) | N6—Se3—C19—N5 | 0.4 (6) |
| N2—Se1—C1—C2 | 179.5 (8) | N6—Se3—C19—C20 | −179.7 (8) |
| N2—C6—C7—C8 | −109.8 (9) | N6—C24—C25—C26 | 105.2 (10) |
| N2—C6—C7—C9 | 13.8 (11) | N6—C24—C25—C27 | −15.9 (12) |
| C1—Se1—N2—C6 | −0.3 (6) | C19—Se3—N6—C24 | −0.7 (6) |
| C1—N1—C5—C4 | −1.5 (11) | C19—N5—C23—C22 | −0.5 (12) |
| C1—N1—C6—N2 | 0.9 (10) | C19—N5—C24—N6 | −0.6 (10) |
| C1—N1—C6—C7 | 177.5 (7) | C19—N5—C24—C25 | 178.5 (7) |
| C1—C2—C3—C4 | −0.5 (12) | C19—C20—C21—C22 | 1.3 (13) |
| C2—C3—C4—C5 | −0.2 (13) | C20—C21—C22—C23 | −0.8 (13) |
| C3—C4—C5—N1 | 1.2 (12) | C21—C22—C23—N5 | 0.4 (13) |
| C5—N1—C1—Se1 | 179.5 (6) | C23—N5—C19—Se3 | −179.0 (6) |
| C5—N1—C1—C2 | 0.7 (11) | C23—N5—C19—C20 | 1.1 (11) |
| C5—N1—C6—N2 | −179.7 (7) | C23—N5—C24—N6 | 178.4 (7) |
| C5—N1—C6—C7 | −3.2 (11) | C23—N5—C24—C25 | −2.6 (12) |
| C6—N1—C1—Se1 | −1.1 (8) | C24—N5—C19—Se3 | 0.0 (8) |
| C6—N1—C1—C2 | −180.0 (7) | C24—N5—C19—C20 | −179.9 (7) |
| C6—N1—C5—C4 | 179.3 (7) | C24—N5—C23—C22 | −179.4 (8) |
| Se2—N4—C15—N3 | 4.0 (9) | Se4—N8—C33—N7 | 0.8 (9) |
| Se2—N4—C15—C16 | −175.0 (6) | Se4—N8—C33—C34 | −177.4 (6) |
| Se2—C10—C11—C12 | 179.6 (6) | Se4—C28—C29—C30 | −179.0 (7) |
| N3—C10—C11—C12 | −0.9 (11) | N7—C28—C29—C30 | 1.8 (12) |
| N3—C15—C16—C17 | −161.4 (7) | N7—C33—C34—C35 | 74.5 (9) |
| N3—C15—C16—C18 | 74.5 (10) | N7—C33—C34—C36 | −160.3 (7) |
| N4—Se2—C10—N3 | 1.6 (5) | N8—Se4—C28—N7 | −1.2 (6) |
| N4—Se2—C10—C11 | −178.9 (8) | N8—Se4—C28—C29 | 179.6 (8) |
| N4—C15—C16—C17 | 17.6 (12) | N8—C33—C34—C35 | −107.3 (9) |
| N4—C15—C16—C18 | −106.5 (10) | N8—C33—C34—C36 | 17.9 (11) |
| C10—Se2—N4—C15 | −3.2 (6) | C28—Se4—N8—C33 | 0.2 (6) |
| C10—N3—C14—C13 | 2.9 (12) | C28—N7—C32—C31 | −1.3 (12) |
| C10—N3—C15—N4 | −2.8 (10) | C28—N7—C33—N8 | −1.9 (10) |
| C10—N3—C15—C16 | 176.3 (7) | C28—N7—C33—C34 | 176.5 (7) |
| C10—C11—C12—C13 | 3.2 (12) | C28—C29—C30—C31 | −2.4 (13) |
| C11—C12—C13—C14 | −2.5 (12) | C29—C30—C31—C32 | 1.1 (13) |
| C12—C13—C14—N3 | −0.7 (12) | C30—C31—C32—N7 | 0.8 (13) |
| C14—N3—C10—Se2 | 177.4 (6) | C32—N7—C28—Se4 | −179.3 (6) |
| C14—N3—C10—C11 | −2.1 (11) | C32—N7—C28—C29 | 0.0 (11) |
| C14—N3—C15—N4 | 180.0 (7) | C32—N7—C33—N8 | 179.3 (7) |
| C14—N3—C15—C16 | −1.0 (11) | C32—N7—C33—C34 | −2.3 (11) |
| C15—N3—C10—Se2 | 0.1 (8) | C33—N7—C28—Se4 | 1.9 (8) |
| C15—N3—C10—C11 | −179.5 (7) | C33—N7—C28—C29 | −178.8 (7) |
| C15—N3—C14—C13 | −180.0 (7) | C33—N7—C32—C31 | 177.4 (7) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C2—H2···Cl1 | 0.95 | 2.62 | 3.327 (10) | 132 |
| C3—H3···Cl2i | 0.95 | 2.67 | 3.598 (9) | 167 |
| C5—H5···Cl1ii | 0.95 | 2.67 | 3.395 (10) | 133 |
| C11—H11···Cl2 | 0.95 | 2.61 | 3.288 (10) | 129 |
| C14—H14···Cl2ii | 0.95 | 2.47 | 3.310 (10) | 147 |
| C18—H18C···Cl4iii | 0.98 | 2.73 | 3.687 (11) | 167 |
| C20—H20···Cl3 | 0.95 | 2.67 | 3.364 (10) | 131 |
| C23—H23···Cl3iv | 0.95 | 2.73 | 3.418 (10) | 130 |
| C29—H29···Cl4 | 0.95 | 2.63 | 3.323 (10) | 130 |
| C30—H30···Cl3v | 0.95 | 2.81 | 3.651 (9) | 148 |
| C32—H32···Cl4ii | 0.95 | 2.76 | 3.452 (9) | 131 |
Symmetry codes: (i) x−1, y−1, z; (ii) x−1, y, z; (iii) −x+2, y+1/2, −z+1/2; (iv) x+1, y, z; (v) −x+1, y−1/2, −z+1/2.
Funding Statement
This work was performed under the support of the Russian Science Foundation (award No. 2273-10007).
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989024000938/ex2079sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989024000938/ex2079Isup2.hkl
Fingerprint plots. DOI: 10.1107/S2056989024000938/ex2079sup3.zip
CCDC reference: 2328546
Additional supporting information: crystallographic information; 3D view; checkCIF report