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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 81| Part 8| August 2025| Pages 662-666
https://doi.org/10.1107/S2056989025005390

Crystal structure and Hirshfeld surface analysis of (E)-1-{2,2-di­bromo-1-[4-(tert-but­yl)phen­yl]ethen­yl}-2-(3,4-di­methyl­phen­yl)diazene

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Namig G. Shikhaliyev,a Jonathan Cisterna,b Ayten M. Gajar,c Ayten A. Niyazova,d Ali N. Khalilov,d Victor N. Khrustalev,e,f Alebel N. Belayg* and Abel M. Maharramovc

aDepartment of Chemical Engineering, Baku Engineering University, Hasan Aliyev Str. 120, AZ 0101 Baku, Azerbaijan, bDepartamento de Química, Universidad Católica del Norte, Av. Angamos 0610, Antofagasta, Chile, cDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, Az 1148, Baku, Azerbaijan, d"Composite Materials" Scientific Research Center, Azerbaijan State Economic University (UNEC), Murtuza Mukhtarov str. 194, Az 1065, Baku, Azerbaijan, ePeoples’ Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow, 117198, Russian Federation, fN. D. Zelinsky Institute of Organic, Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation, and gDepartment of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia
*Correspondence e-mail: [email protected]

Edited by S. P. Kelley, University of Missouri-Columbia, USA (Received 11 March 2025; accepted 17 June 2025; online 1 July 2025)

The title azo compound, C20H22Br2N2, crystallizes in the triclinic space group P1 (No. 2) with two independent mol­ecules in the asymmetric unit. The mol­ecular structure was analyzed using spectroscopic and crystallographic techniques, confirming the expected configuration and electronic environment. Hirshfeld surface analysis revealed key non-covalent inter­actions such as C—H⋯π, C—H⋯Br, π–π stacking, and halogen bonding, which consolidate the crystal structure. The study provides valuable insights into the structural features and inter­molecular inter­actions of this brominated azo compound, which may have potential applications in optoelectronic materials, dyes, and mol­ecular switches.

CCDC reference: 2465012

Similar articles

1. Chemical context

Azo compounds represent a significant class of organic mol­ecules characterized by a diazenyl (–N=N–) functional group linking two aromatic systems (Shikhaliyev et al., 2018[Shikhaliyev, N. Q., Ahmadova, N. E., Gurbanov, A. V., Maharramov, A. M., Mammadova, G. Z., Nenajdenko, V. G., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2018). Dyes Pigments 150, 377-381.]; Naghiyev et al., 2019[Naghiyev, F., Mamedov, I., Khrustalev, V., Shixaliyev, N. & Maharramov, A. (2019). J. Chin. Chem. Soc. 66, 253-256.]). These compounds have garnered considerable inter­est due to their diverse applications in dyes, pigments, pharmaceuticals, and advanced materials, including liquid crystals and organic semiconductors (Shixaliyev et al., 2013[Shixaliyev, N. Q., Maharramov, A. M., Gurbanov, A. V., Gurbanova, N. V., Nenajdenko, V. G., Muzalevskiy, V. M., Mahmudov, K. T. & Kopylovich, M. N. (2013). J. Mol. Struct. 1041, 213-218.]; Shikhaliyev et al., 2019[Shikhaliyev, N. G., Suleymanova, G. T., İsrayilova, A. A., Ganbarov, K. G., Babayeva, G. V., Garazadeh, K. A., Mammadova, G. Z. & Nenajdenko, V. G. (2019). Arkivoc 2019, 64-73.]; Tahirli et al., 2024[Tahirli, S., Sadeghian, N., Aliyeva, F., Sujayev, A., Günay, S., Erden, Y., Shikhaliyev, N., Kaya, S., Mehtap Özden, E., Chiragov, F., Berisha, A. & Taslimi, P. (2024). Chem. Biodivers. 21, e202301861.]). The introduction of various substituents on the aromatic rings can fine-tune their electronic, optical, and chemical properties, making them highly versatile for industrial and scientific applications (Gurbanov et al., 2021[Gurbanov, A. V., Mertsalov, D. F., Zubkov, F. I., Nadirova, M. A., Nikitina, E. V., Truong, H. H., Grigoriev, M. S., Zaytsev, V. P., Mahmudov, K. T. & Pombeiro, A. J. L. (2021). Crystals 11, 1-10.]; Mahmoudi et al., 2021[Mahmoudi, G., Zangrando, E., Miroslaw, B., Gurbanov, A. V., Babashkina, M. G., Frontera, A. & Safin, D. A. (2021). Inorg. Chim. Acta 519, 120279, 1-10.]).

The structure under investigation features a di­bromo­vinyl­idenebenzyl moiety and a methyl-substituted phenyl group linked via an azo (–N=N–) bridge (Israyilova et al., 2016[Israyilova, A., Buroni, S., Forneris, F., Scoffone, V. C., Shixaliyev, N. Q., Riccardi, G. & Chiarelli, L. R. (2016). PLoS One 11, e0167350.]; Çelikesir et al., 2022[Çelikesir, S. T., Akkurt, M., Shikhaliyev, N. Q., Mammadova, N. A., Suleymanova, G. T., Khrustalev, V. N. & Bhattarai, A. (2022). Acta Cryst. E78, 404-408.]). The di­bromo­alkene moiety enhances the reactivity, allowing for further functionalization and potential applications in cross-coupling reactions, while alkyl substituents on the phenyl ring contribute to improved solubility and stability (Dobrounig et al., 2017[Dobrounig, P., Trobe, M. & Breinbauer, R. (2017). Monatsh. Chem. 148, 3-35.]; Atioğlu et al., 2022a[Atioğlu, Z., Akkurt, M., Shikhaliyev, N. Q., Mammadova, N. A., Babayeva, G. V., Khrustalev, V. N. & Bhattarai, A. (2022a). Acta Cryst. E78, 530-535.],b[Atioğlu, Z., Akkurt, M., Shikhaliyev, N. Q., Mammadova, N. A., Babayeva, G. V., Khrustalev, V. N. & Bhattarai, A. (2022b). Acta Cryst. E78, 804-808.]; Khalilov et al., 2022[Khalilov, A. N., Khrustalev, V. N., Tereshina, T. A., Akkurt, M., Rzayev, R. M., Akobirshoeva, A. A. & Mamedov, İ. G. (2022). Acta Cryst. E78, 525-529.]). Although the tert-butyl­phenyl ring is electronically decoupled due to the lack of conjugation with the azo and vinyl units, the compound still contains a conjugated π-system involving the diazo group and the p-methyl­phenyl ring. This partial conjugation may contribute to inter­esting photophysical and electronic properties, which are relevant for potential applications in azo dyes, mol­ecular switches, and optoelectronic materials., azo dyes, and mol­ecular switches (Akkurt et al., 2022[Akkurt, M., Yıldırım, S. Ö., Shikhaliyev, N. Q., Mammadova, N. A., Niyazova, A. A., Khrustalev, V. N. & Bhattarai, A. (2022). Acta Cryst. E78, 732-736.]; Shikhaliyev et al., 2021[Shikhaliyev, N. G., Maharramov, A. M., Suleymanova, G. T., Babazade, A. A., Nenajdenko, V. G., Khrustalev, V. N., Novikov, A. S. & Tskhovrebov, A. G. (2021). Mendeleev Commun. 31, 677-679.]).

While synthetic azo dyes have been widely studied and commercially utilized, naturally occurring dyes containing the azo (–N=N–) functional group are infrequent (Özkaraca et al., 2020a[Özkaraca, K., Akkurt, M., Shikhaliyev, N. Q., Askerova, U. F., Suleymanova, G. T., Shikhaliyeva, I. M. & Bhattarai, A. (2020a). Acta Cryst. E76, 811-815.],b[Özkaraca, K., Akkurt, M., Shikhaliyev, N. Q., Askerova, U. F., Suleymanova, G. T., Mammadova, G. Z. & Shadrack, D. M. (2020b). Acta Cryst. E76, 1251-1254.]). Most natural dyes are based on anthra­quinone, flavonoid, or indigoid chromophores. Despite their limited natural occurrence, azo compounds are extensively synthesized because of their excellent color stability, tunability, and strong chromophoric properties (Magerramov et al., 2018[Magerramov, A. M., Naghiyev, F. N., Mamedova, G. Z., Asadov, K. A. & Mamedov, I. G. (2018). Russ. J. Org. Chem. 54, 1731-1734.]; Benkhaya et al., 2020[Benkhaya, S., M'rabet, S. & El Harfi, A. (2020). Heliyon, 6, e03271.]).

[Scheme 1]

Given the significance of azo compounds in material science and organic synthesis, the present study reports the synthesis and crystal structure of (E)-1-{2,2-di­bromo-1-[4-(tert-but­yl)phen­yl]ethen­yl}-2-(3,4-di­methyl­phen­yl)diazene in which the di­bromo­vinyl and tert-butyl groups were incorporated to modulate the azo scaffold's reactivity and solubility profiles.

2. Structural commentary

The title compound crystallizes in the triclinic cell system with space group PMathematical equation (No. 2), with two mol­ecules in the asymmetric unit (Z = 4). The mol­ecular structure of the compound agrees with the spectroscopic characterization and the proposed structure, in a centrosymmetric setting, with normal bond distances (Allen et al., 1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2 pp. S1-S19.]) and angles, being the E-isomer confirmed as mol­ecular structure within the crystal (see Fig. 1[link]). The independent mol­ecules are labeled fragment 1 and 2, correlative and sorted atom labels, The diazo bond environments in each mol­ecule are practically coplanar, apart from the 4-tert-butyl­phenyl moiety in both cases. There is a lack of conjugation between the tert-butyl­phenyl group and the adjacent vinyl group, with dihedral angles of 89.2 (2) and 66.8 (2)° for fragments 1 and 2, respectively. The dihedral angles between these two fragments indicate that in both cases the aromatic ring is twisted out of planarity relative to the vinyl moiety, effectively insulating it electronically from the azo group. This lack of conjugation may have important implications for the electronic distribution and potential reactivity of the mol­ecule.

[Figure 1]
Figure 1
Ellipsoid plots (30% probability) of fragments 1(left) and 2 (right). Hydrogen atoms are omitted for the sake of clarity.

The origin of this non-conjugated geometry warrants further consideration. One possible explanation is steric hindrance introduced by the bulky tert-butyl substituent, which may prevent the coplanarity required for extended π-conjugation. Alternatively, this conformation could be stabilized or enforced by crystal-packing effects, as inter­molecular forces may favor a geometry that minimizes unfavorable contacts or facilitates specific packing motifs, such as herringbone arrangements.

3. Supra­molecular features

The crystal packing of the title compound does not exhibit geometrical parameters consistent with classical hydrogen bonds (Steiner, 2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]). Instead, the structure is consolidated by inter­molecular inter­actions such as H⋯π, C—H⋯Br, halogen bonds, and parallel-displaced π–π stacking (see Fig. 2[link]). The π–π inter­actions exceed conventional parameters for this type of inter­action (Carter-Fenk & Herbert, 2020[Carter-Fenk, K. & Herbert, J. M. (2020). Phys. Chem. Chem. Phys. 22, 24870-24886.]). The centroid–centroid distances are 5.5060 (14) and 5.9474 (13) Å (red dotted lines), with perpendicular ring plane separations of 3.1104 (9) and 2.2010 (9) Å (blue dotted lines). The slippage values are 4.543 and 5.060 Å (green dotted lines), observed between the C13–C18 ring and its symmetry equivalent at 1 − x, 1 − y, 2 − z) and between the C13–C18 and C33–C38(x, 2 − y, 1 − z) rings, respectively (Fig. 3[link]).

[Figure 2]
Figure 2
C—H⋯Br interactions and halogen bonds found in the crystal structure of the title compound.
[Figure 3]
Figure 3
π–π-like stacking in the title compound.

It is worth noting that a Z′ value of 2 for two conformationally identical mol­ecules is uncommon. This appears to arise from the fact that, although the mol­ecules adopt a herringbone packing motif, they cannot do so without a relative offset due to the dihedral angle. This observation suggests that the mol­ecular conformation is particularly stable.

Hirshfeld surface analysis was conducted for each fragment individually to gain a deeper understanding of all contributions. These inter­actions are visualized as red (dnorm < vdW radii), white (dnorm = vdW radii), and blue (dnorm > vdW radii) spots on the dnorm surfaces for all compounds along with fingerprint plots mapped with dnorm (where dnorm = di + de) (Fig. 4[link]). H⋯Br contacts are observed to contribute around 20% with di + de ≃ 2.1 Å, generating a dimeric setting between the two fragments within the crystal structure. This is observed in similar compounds with a similar behavior without the formation of supra­molecular aggregates in the crystal structure (Maharramov et al. 2019[Maharramov, A. M., Duruskari, G. S., Mammadova, G. Z., Khalilov, A. N., Aslanova, J. M., Cisterna, J., Cárdenas, A. & Brito, I. (2019). J. Chil. Chem. Soc. 64, 4441-4447.]). H⋯π contacts contribute around 20% with di + de ≃ 3.0 Å, generating the stacking between the fragments along the a-axis direction. Although weaker than conventional hydrogen bonds, these inter­actions can play a crucial role in crystal packing, mol­ecular recognition, and other supra­molecular processes (Nagarajan et al. 2014[Nagarajan, K., Rajagopal, S. K. & Hariharan, M. (2014). CrystEngComm 16, 8946-8949.]; Rajagopal et al. 2016[Rajagopal, S. K., Salini, P. S. & Hariharan, M. (2016). Cryst. Growth Des. 16, 4567-4573.]). H⋯H contacts and π–π contacts make negligible contributions. Br⋯Br contacts are observed with a contribution of around 3.5%, and di + de ≃ 3.7 and 4.5 Å, generating a tetra­mer in the crystal structure along the b-axis direction. These inter­actions, although often weak, are recognized for their capacity to influence the overall packing and consolidation of mol­ecular crystals (Marek et al. 2018[Marek, P. H., Urban, M. & Madura, I. D. (2018). Acta Cryst. C74, 1509-1517.]; Cavallo et al. 2016[Cavallo, G., Metrangolo, P., Milani, R., Pilati, T., Priimagi, A., Resnati, G. & Terraneo, G. (2016). Chem. Rev. 116, 2478-2601.]; Varadwaj et al. 2019[Varadwaj, P. R., Varadwaj, A. & Marques, H. M. (2019). Inorganics 7, 40, 1-63.]).

[Figure 4]
Figure 4
Overall Hirshfeld surface for fragments 1 and 2 and their respective overall fingerprint plots.

It is also worth noting that the presence of electron-donating substituents on the mol­ecule can modulate the electron-density distribution, potentially altering the nature and strength of inter­actions involving bromine atoms. This suggests that substituent effects may play a role not only in intra­molecular properties, but also in dictating the inter­molecular landscape of the crystal packing.

4. Database survey

A Cambridge Structural Database (CSD; 2022.3 Version, November 2024 update; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) search for the (E)-1-{2,2-di­bromo-1-[4-(tert-but­yl)phen­yl]vin­yl}-2-(3,4-di­methyl­phen­yl)diazene unit yielded 90 hits. Refining the search to include structures containing Br atoms gave just four compounds closely resembling the title compound, viz. ECUDAL [(I); Atioğlu et al., 2022b[Atioğlu, Z., Akkurt, M., Shikhaliyev, N. Q., Mammadova, N. A., Babayeva, G. V., Khrustalev, V. N. & Bhattarai, A. (2022b). Acta Cryst. E78, 804-808.]], HEHKEO [(II); Akkurt et al., 2022[Akkurt, M., Yıldırım, S. Ö., Shikhaliyev, N. Q., Mammadova, N. A., Niyazova, A. A., Khrustalev, V. N. & Bhattarai, A. (2022). Acta Cryst. E78, 732-736.]], PAXDOL [(III); Çelikesir et al., 2022[Çelikesir, S. T., Akkurt, M., Shikhaliyev, N. Q., Mammadova, N. A., Suleymanova, G. T., Khrustalev, V. N. & Bhattarai, A. (2022). Acta Cryst. E78, 404-408.]], and TAZDIL [(IV); Atioğlu et al., 2022a[Atioğlu, Z., Akkurt, M., Shikhaliyev, N. Q., Mammadova, N. A., Babayeva, G. V., Khrustalev, V. N. & Bhattarai, A. (2022a). Acta Cryst. E78, 530-535.]].

In the crystal structure of (I)[link], the mol­ecules form inversion dimers via short halogen–halogen contacts [Br3⋯Br3 = 4.0103 (6) Å, C12—Br3⋯Br3 = 72.23 (6)°], which are shorter than the van der Waals radius sum of 5.55 Å for two bromine atoms. Additional directional inter­actions include Br1⋯O2 contacts [3.137 (19) Å] along the [010] direction and π–π stacking inter­actions between aromatic rings are also present, with centroid–centroid distances of 3.7305 (11) Å [perpendicular ring plane separations of 3.3964 (8) and 3.1119 (8) Å, and slippage values of 2.057 and 1.543 Å].

In (II), the structure features the same halogen contacts as in (I)[link], but additionally presents π⋯Br contacts with a Br1–4-nitro mono-substituted ring distance of 3.546 (17) Å. Unlike in compound (I)[link], no π–π stacking inter­actions are observed in this structure.

The crystal structure of (III) exhibits inter­molecular hydrogen-bonding inter­actions between the aromatic rings and the oxygen of the nitro moiety [D⋯H = 2.51 Å, D⋯A = 3.3244 (18) Å, D—H⋯A =144°. Br⋯O contacts (2.983 Å) are also present.

Finally in (IV), several hydrogen-bonding inter­actions consolidate the crystal structure due to the inversion center present in the unit cell. π–π stacking inter­actions are found, but at larger distances than conventional values (weighted distance = 4.079 Å). The structure also exhibits halogen–π inter­actions, with a mean distance of 3.503 Å.

5. Synthesis and crystallization

The title compound was obtained using a previously reported procedure (Shikhaliyev et al., 2018[Shikhaliyev, N. Q., Ahmadova, N. E., Gurbanov, A. V., Maharramov, A. M., Mammadova, G. Z., Nenajdenko, V. G., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2018). Dyes Pigments 150, 377-381.]), with appropriate modifications for the brominated analog. A 20 ml screw-neck vial was charged with DMSO (10 mL), (E)-1-[4-(tert-but­yl)benzyl­idene]-2-(3,4-di­methyl­phen­yl)hydrazine (281 mg, 1 mmol), tetra­methyl­ethylenedi­amine (TMEDA) (295 mg, 2.5 mmol), CuCl (2 mg, 0.02 mmol) and CBr4 (3 mmol). After 1–3 h (until TLC analysis showed complete consumption of corresponding Schiff base), the reaction mixture was poured into an 0.01 M solution of HCl (100 ml, pH = 2), and extracted with di­chloro­methane (3 × 20 ml). The combined organic phase was washed with water (3 × 50 ml) and brine (30 ml), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel using appropriate mixtures of hexane and di­chloro­methane (3:1, v/v). The resulting title compound was obtained as an orange crystalline solid, m.p. 388 K; yield: 34%.

1H NMR (300 MHz, CDCl3) δ 7.69 (s, 1H), 7.67 (d, J = 8 Hz, 1H), 7.54 (d, J = 8.4 Hz, 2H), 7.32 (d, J = 8 Hz, 1H),7.21 (d, J = 8.4 Hz, 2H), 2.33 (s, 6H), 1.44 (s, 9H). 13C NMR (75 MHz, CDCl3) δ 153.7, 152.3, 151.9, 142.6, 138.5, 134.6, 132.5, 127.9, 127.7, 125.7, 123.8, 121.5, 34.5, 31.9, 20.7, 19.4.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. Hydrogen atoms were found in difference-Fourier maps, and included in the refinement using riding models, with constrained distances set to 0.95 Å (Csp2—H) and 0.98 Å (RCH3). Uiso(H) parameters were set to values of either 1.2Ueq or 1.5Ueq (RCH3 only) of the attached atom.

Table 1
Experimental details

Crystal data
Chemical formula C20H22Br2N2
Mr 450.20
Crystal system, space group Triclinic, PMathematical equation
Temperature (K) 100
a, b, c (Å) 9.89357 (5), 12.23384 (7), 17.12566 (9)
α, β, γ (°) 76.6038 (5), 89.3055 (4), 73.3449 (5)
V (Å3) 1928.56 (2)
Z 4
Radiation type Cu Kα
μ (mm−1) 5.34
Crystal size (mm) 0.31 × 0.25 × 0.21
 
Data collection
Diffractometer XtaLAB Synergy, Dualflex, HyPix
Absorption correction Multi-scan (CrysAlis PRO; Rigaku OD, 2021[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.])
Tmin, Tmax 0.504, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 59739, 8330, 7876
Rint 0.049
(sin θ/λ)max (Å−1) 0.638
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.098, 1.09
No. of reflections 8330
No. of parameters 443
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.01, −0.86
Computer programs: CrysAlis PRO (Rigaku OD, 2021[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

CCDC reference: 2465012

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989025005390/ev2015sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2056989025005390/ev2015Isup3.cml

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025005390/ev2015Isup4.hkl

checkCIF report


Computing details top

(E)-1-{2,2-Dibromo-1-[4-(tert-butyl)phenyl]ethenyl}-\ 2-(3,4-dimethylphenyl)diazene top
Crystal data top
C20H22Br2N2Z = 4
Mr = 450.20F(000) = 904
Triclinic, P1Dx = 1.551 Mg m−3
a = 9.89357 (5) ÅCu Kα radiation, λ = 1.54184 Å
b = 12.23384 (7) ÅCell parameters from 36360 reflections
c = 17.12566 (9) Åθ = 2.7–79.4°
α = 76.6038 (5)°µ = 5.34 mm−1
β = 89.3055 (4)°T = 100 K
γ = 73.3449 (5)°Prism, red
V = 1928.56 (2) Å30.31 × 0.25 × 0.21 mm
Data collection top
XtaLAB Synergy, Dualflex, HyPix
diffractometer		8330 independent reflections
Radiation source: micro-focus sealed X-ray tube7876 reflections with I > 2σ(I)
Detector resolution: 0.78 pixels mm-1Rint = 0.049
φ and ω scansθmax = 79.6°, θmin = 2.7°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2021)		h = −11→12
Tmin = 0.504, Tmax = 1.000k = −15→15
59739 measured reflectionsl = −21→21
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0523P)2 + 1.7466P]
where P = (Fo2 + 2Fc2)/3
8330 reflections(Δ/σ)max = 0.001
443 parametersΔρmax = 1.01 e Å−3
0 restraintsΔρmin = −0.86 e Å−3
Special details top

Experimental. CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
xyzUiso*/Ueq
Br10.39020 (3)0.65399 (2)0.49638 (2)0.02673 (8)
Br20.34648 (3)0.87116 (2)0.57292 (2)0.02590 (8)
N10.35259 (18)0.69310 (16)0.72925 (11)0.0193 (3)
N20.34989 (19)0.62342 (17)0.79595 (11)0.0209 (3)
C10.3699 (2)0.63915 (18)0.66366 (12)0.0189 (4)
C20.3679 (2)0.70933 (19)0.59018 (13)0.0210 (4)
C30.3979 (2)0.50950 (18)0.67648 (12)0.0188 (4)
C40.2892 (2)0.4581 (2)0.67752 (13)0.0216 (4)
H40.19390.50620.66810.026*
C50.3195 (2)0.33693 (19)0.69232 (13)0.0208 (4)
H50.24410.30300.69340.025*
C60.4588 (2)0.26337 (18)0.70571 (11)0.0177 (4)
C70.5661 (2)0.31621 (19)0.70445 (13)0.0201 (4)
H70.66160.26850.71340.024*
C80.5364 (2)0.43807 (19)0.69034 (13)0.0222 (4)
H80.61140.47220.69020.027*
C90.4882 (2)0.12987 (18)0.72170 (12)0.0200 (4)
C100.4240 (3)0.0863 (2)0.80055 (15)0.0304 (5)
H10A0.44450.00070.81180.046*
H10B0.32150.12270.79570.046*
H10C0.46510.10760.84460.046*
C110.4221 (3)0.0985 (2)0.65293 (17)0.0360 (6)
H11A0.45940.12990.60210.054*
H11B0.31930.13260.65020.054*
H11C0.44530.01290.66240.054*
C120.6470 (3)0.0659 (2)0.72932 (16)0.0295 (5)
H12A0.69120.08350.77390.044*
H12B0.68980.09230.67920.044*
H12C0.6614−0.01900.73970.044*
C130.3361 (2)0.6775 (2)0.86203 (13)0.0221 (4)
C140.3347 (2)0.6052 (2)0.93741 (13)0.0235 (4)
H140.34050.52520.94160.028*
C150.3249 (2)0.6471 (2)1.00761 (14)0.0240 (4)
C160.3187 (2)0.7646 (2)1.00061 (14)0.0247 (4)
C170.3173 (2)0.8378 (2)0.92485 (14)0.0250 (4)
H170.31020.91810.92050.030*
C180.3259 (2)0.7964 (2)0.85567 (14)0.0237 (4)
H180.32500.84760.80450.028*
C190.3217 (3)0.5654 (2)1.08795 (14)0.0311 (5)
H19A0.32610.48751.08020.047*
H19B0.23410.59641.11320.047*
H19C0.40300.55901.12270.047*
C200.3146 (3)0.8120 (2)1.07465 (15)0.0323 (5)
H20A0.31830.89341.05920.048*
H20B0.39580.76401.11160.048*
H20C0.22700.80951.10130.048*
Br30.24367 (3)0.15502 (2)0.41709 (2)0.02955 (8)
Br40.19508 (3)0.36576 (2)0.50063 (2)0.03296 (8)
N30.1094 (2)0.51443 (17)0.33545 (11)0.0220 (4)
N40.07769 (19)0.58727 (16)0.26830 (11)0.0204 (3)
C210.1507 (2)0.39520 (19)0.33196 (13)0.0214 (4)
C220.1889 (2)0.3189 (2)0.40421 (13)0.0241 (4)
C230.1561 (2)0.35732 (18)0.25522 (13)0.0206 (4)
C240.0330 (2)0.3772 (2)0.20823 (14)0.0233 (4)
H24−0.05600.41620.22500.028*
C250.0405 (2)0.3402 (2)0.13751 (13)0.0227 (4)
H25−0.04420.35380.10650.027*
C260.1699 (2)0.28308 (18)0.11024 (12)0.0194 (4)
C270.2918 (2)0.26499 (19)0.15739 (13)0.0213 (4)
H270.38110.22740.14030.026*
C280.2851 (2)0.30098 (19)0.22908 (13)0.0219 (4)
H280.36960.28690.26040.026*
C290.1723 (2)0.2451 (2)0.03092 (13)0.0230 (4)
C300.1064 (3)0.3543 (2)−0.03732 (14)0.0319 (5)
H30A0.11400.3318−0.08890.048*
H30B0.15680.4128−0.03830.048*
H30C0.00670.3877−0.02820.048*
C310.3219 (3)0.1862 (3)0.01054 (16)0.0360 (6)
H31A0.36530.11660.05360.054*
H31B0.37820.24140.00500.054*
H31C0.31850.1626−0.04020.054*
C320.0853 (3)0.1578 (2)0.03751 (15)0.0278 (5)
H32A−0.01350.19690.04540.042*
H32B0.12330.09090.08330.042*
H32C0.09050.1299−0.01200.042*
C330.0451 (2)0.70618 (19)0.27538 (13)0.0203 (4)
C340.0515 (2)0.7391 (2)0.34773 (13)0.0217 (4)
H340.07370.68070.39690.026*
C350.0256 (2)0.8566 (2)0.34845 (14)0.0226 (4)
C36−0.0068 (2)0.9434 (2)0.27575 (14)0.0230 (4)
C37−0.0160 (2)0.9096 (2)0.20417 (14)0.0238 (4)
H37−0.03990.96780.15500.029*
C380.0092 (2)0.7919 (2)0.20356 (13)0.0230 (4)
H380.00190.77010.15440.028*
C390.0356 (3)0.8902 (2)0.42721 (14)0.0281 (5)
H39A0.05290.82010.47160.042*
H39B−0.05330.94760.43410.042*
H39C0.11350.92490.42700.042*
C40−0.0267 (3)1.0705 (2)0.27440 (15)0.0279 (5)
H40A−0.10931.09920.30420.042*
H40B−0.04141.11690.21860.042*
H40C0.05751.07820.29950.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04118 (15)0.02158 (13)0.01649 (12)−0.00428 (10)0.00179 (9)−0.00884 (9)
Br20.04033 (14)0.01623 (12)0.02161 (12)−0.00799 (9)0.00190 (9)−0.00576 (9)
N10.0230 (8)0.0182 (8)0.0171 (8)−0.0051 (7)−0.0006 (6)−0.0062 (7)
N20.0222 (8)0.0228 (9)0.0183 (8)−0.0068 (7)−0.0011 (6)−0.0056 (7)
C10.0225 (10)0.0165 (9)0.0177 (9)−0.0035 (7)−0.0009 (7)−0.0066 (7)
C20.0279 (10)0.0178 (10)0.0188 (10)−0.0057 (8)0.0004 (8)−0.0083 (8)
C30.0271 (10)0.0158 (9)0.0154 (9)−0.0069 (8)−0.0002 (7)−0.0065 (7)
C40.0219 (10)0.0219 (10)0.0222 (10)−0.0042 (8)0.0011 (8)−0.0105 (8)
C50.0234 (10)0.0218 (10)0.0210 (10)−0.0095 (8)0.0022 (8)−0.0090 (8)
C60.0275 (10)0.0178 (9)0.0105 (8)−0.0086 (8)0.0029 (7)−0.0060 (7)
C70.0206 (9)0.0184 (10)0.0204 (10)−0.0041 (7)0.0002 (7)−0.0046 (8)
C80.0238 (10)0.0200 (10)0.0243 (10)−0.0092 (8)−0.0001 (8)−0.0042 (8)
C90.0281 (10)0.0153 (9)0.0168 (9)−0.0065 (8)0.0013 (8)−0.0041 (7)
C100.0379 (13)0.0255 (11)0.0283 (12)−0.0130 (10)0.0072 (10)−0.0029 (9)
C110.0543 (16)0.0242 (12)0.0329 (13)−0.0115 (11)−0.0082 (11)−0.0127 (10)
C120.0348 (12)0.0180 (10)0.0349 (13)−0.0063 (9)0.0047 (10)−0.0065 (9)
C130.0197 (10)0.0289 (11)0.0184 (10)−0.0064 (8)−0.0009 (7)−0.0078 (8)
C140.0246 (10)0.0237 (10)0.0215 (10)−0.0066 (8)−0.0006 (8)−0.0048 (8)
C150.0212 (10)0.0265 (11)0.0213 (10)−0.0055 (8)0.0003 (8)−0.0013 (8)
C160.0234 (10)0.0279 (11)0.0234 (11)−0.0072 (8)−0.0004 (8)−0.0073 (9)
C170.0290 (11)0.0234 (11)0.0241 (11)−0.0077 (9)0.0019 (8)−0.0089 (9)
C180.0249 (10)0.0251 (11)0.0214 (10)−0.0063 (8)−0.0005 (8)−0.0074 (8)
C190.0415 (13)0.0293 (12)0.0204 (11)−0.0097 (10)0.0025 (9)−0.0027 (9)
C200.0423 (13)0.0351 (13)0.0245 (11)−0.0148 (11)0.0055 (10)−0.0125 (10)
Br30.04488 (15)0.01919 (13)0.02299 (13)−0.00876 (10)−0.00063 (10)−0.00254 (9)
Br40.05341 (17)0.02801 (14)0.01713 (12)−0.01054 (11)−0.00191 (10)−0.00619 (10)
N30.0276 (9)0.0195 (9)0.0194 (8)−0.0081 (7)0.0000 (7)−0.0041 (7)
N40.0227 (8)0.0203 (9)0.0201 (8)−0.0077 (7)0.0003 (6)−0.0066 (7)
C210.0249 (10)0.0215 (10)0.0190 (10)−0.0080 (8)0.0000 (8)−0.0055 (8)
C220.0332 (11)0.0212 (10)0.0190 (10)−0.0085 (9)−0.0002 (8)−0.0063 (8)
C230.0282 (10)0.0171 (9)0.0174 (9)−0.0082 (8)−0.0002 (8)−0.0037 (8)
C240.0227 (10)0.0237 (10)0.0235 (10)−0.0057 (8)0.0018 (8)−0.0073 (8)
C250.0230 (10)0.0231 (10)0.0222 (10)−0.0060 (8)−0.0027 (8)−0.0063 (8)
C260.0241 (10)0.0174 (9)0.0156 (9)−0.0060 (7)−0.0001 (7)−0.0019 (7)
C270.0221 (10)0.0205 (10)0.0205 (10)−0.0058 (8)0.0008 (8)−0.0038 (8)
C280.0233 (10)0.0211 (10)0.0208 (10)−0.0070 (8)−0.0031 (8)−0.0032 (8)
C290.0288 (11)0.0231 (10)0.0181 (10)−0.0084 (8)0.0001 (8)−0.0059 (8)
C300.0501 (15)0.0291 (12)0.0187 (10)−0.0178 (11)−0.0060 (10)−0.0016 (9)
C310.0335 (13)0.0521 (16)0.0266 (12)−0.0105 (11)0.0049 (10)−0.0203 (12)
C320.0375 (12)0.0253 (11)0.0249 (11)−0.0122 (9)0.0007 (9)−0.0103 (9)
C330.0211 (9)0.0194 (10)0.0211 (10)−0.0066 (8)0.0008 (7)−0.0051 (8)
C340.0229 (10)0.0230 (10)0.0182 (10)−0.0066 (8)0.0009 (7)−0.0033 (8)
C350.0208 (10)0.0243 (11)0.0230 (10)−0.0047 (8)0.0012 (8)−0.0081 (9)
C360.0199 (10)0.0210 (10)0.0270 (11)−0.0039 (8)0.0006 (8)−0.0063 (9)
C370.0264 (10)0.0217 (10)0.0212 (10)−0.0073 (8)−0.0027 (8)−0.0005 (8)
C380.0257 (10)0.0254 (11)0.0185 (10)−0.0083 (8)−0.0018 (8)−0.0051 (8)
C390.0366 (12)0.0241 (11)0.0232 (11)−0.0043 (9)0.0000 (9)−0.0104 (9)
C400.0303 (11)0.0209 (11)0.0311 (12)−0.0048 (9)−0.0007 (9)−0.0070 (9)
Geometric parameters (Å, º) top
Br1—C21.870 (2)Br3—C221.881 (2)
Br2—C21.882 (2)Br4—C221.876 (2)
N1—N21.262 (3)N3—N41.260 (3)
N1—C11.415 (3)N3—C211.413 (3)
N2—C131.424 (3)N4—C331.431 (3)
C1—C21.346 (3)C21—C221.349 (3)
C1—C31.493 (3)C21—C231.487 (3)
C3—C81.387 (3)C23—C281.389 (3)
C3—C41.391 (3)C23—C241.398 (3)
C4—C51.388 (3)C24—C251.382 (3)
C4—H40.9500C24—H240.9500
C5—C61.401 (3)C25—C261.403 (3)
C5—H50.9500C25—H250.9500
C6—C71.390 (3)C26—C271.393 (3)
C6—C91.533 (3)C26—C291.532 (3)
C7—C81.397 (3)C27—C281.392 (3)
C7—H70.9500C27—H270.9500
C8—H80.9500C28—H280.9500
C9—C111.527 (3)C29—C311.525 (3)
C9—C101.533 (3)C29—C321.537 (3)
C9—C121.533 (3)C29—C301.540 (3)
C10—H10A0.9800C30—H30A0.9800
C10—H10B0.9800C30—H30B0.9800
C10—H10C0.9800C30—H30C0.9800
C11—H11A0.9800C31—H31A0.9800
C11—H11B0.9800C31—H31B0.9800
C11—H11C0.9800C31—H31C0.9800
C12—H12A0.9800C32—H32A0.9800
C12—H12B0.9800C32—H32B0.9800
C12—H12C0.9800C32—H32C0.9800
C13—C141.388 (3)C33—C381.392 (3)
C13—C181.406 (3)C33—C341.396 (3)
C14—C151.405 (3)C34—C351.389 (3)
C14—H140.9500C34—H340.9500
C15—C161.398 (3)C35—C361.408 (3)
C15—C191.508 (3)C35—C391.511 (3)
C16—C171.393 (3)C36—C371.393 (3)
C16—C201.507 (3)C36—C401.505 (3)
C17—C181.385 (3)C37—C381.391 (3)
C17—H170.9500C37—H370.9500
C18—H180.9500C38—H380.9500
C19—H19A0.9800C39—H39A0.9800
C19—H19B0.9800C39—H39B0.9800
C19—H19C0.9800C39—H39C0.9800
C20—H20A0.9800C40—H40A0.9800
C20—H20B0.9800C40—H40B0.9800
C20—H20C0.9800C40—H40C0.9800
N2—N1—C1113.51 (17)N4—N3—C21115.01 (18)
N1—N2—C13113.24 (18)N3—N4—C33112.37 (18)
C2—C1—N1116.73 (18)C22—C21—N3113.99 (19)
C2—C1—C3121.99 (18)C22—C21—C23123.0 (2)
N1—C1—C3121.17 (18)N3—C21—C23122.99 (19)
C1—C2—Br1122.95 (16)C21—C22—Br4123.41 (17)
C1—C2—Br2123.01 (16)C21—C22—Br3122.78 (17)
Br1—C2—Br2114.03 (11)Br4—C22—Br3113.81 (12)
C8—C3—C4119.14 (19)C28—C23—C24118.8 (2)
C8—C3—C1118.81 (18)C28—C23—C21120.03 (19)
C4—C3—C1122.02 (19)C24—C23—C21121.2 (2)
C5—C4—C3120.2 (2)C25—C24—C23120.2 (2)
C5—C4—H4119.9C25—C24—H24119.9
C3—C4—H4119.9C23—C24—H24119.9
C4—C5—C6121.55 (19)C24—C25—C26121.8 (2)
C4—C5—H5119.2C24—C25—H25119.1
C6—C5—H5119.2C26—C25—H25119.1
C7—C6—C5117.50 (19)C27—C26—C25117.30 (19)
C7—C6—C9122.46 (19)C27—C26—C29123.09 (19)
C5—C6—C9120.04 (18)C25—C26—C29119.61 (18)
C6—C7—C8121.32 (19)C28—C27—C26121.3 (2)
C6—C7—H7119.3C28—C27—H27119.3
C8—C7—H7119.3C26—C27—H27119.3
C3—C8—C7120.33 (19)C23—C28—C27120.64 (19)
C3—C8—H8119.8C23—C28—H28119.7
C7—C8—H8119.8C27—C28—H28119.7
C11—C9—C6110.07 (18)C31—C29—C26112.15 (18)
C11—C9—C10109.4 (2)C31—C29—C32108.6 (2)
C6—C9—C10109.04 (18)C26—C29—C32109.08 (18)
C11—C9—C12108.1 (2)C31—C29—C30108.6 (2)
C6—C9—C12111.90 (18)C26—C29—C30108.85 (18)
C10—C9—C12108.28 (19)C32—C29—C30109.58 (19)
C9—C10—H10A109.5C29—C30—H30A109.5
C9—C10—H10B109.5C29—C30—H30B109.5
H10A—C10—H10B109.5H30A—C30—H30B109.5
C9—C10—H10C109.5C29—C30—H30C109.5
H10A—C10—H10C109.5H30A—C30—H30C109.5
H10B—C10—H10C109.5H30B—C30—H30C109.5
C9—C11—H11A109.5C29—C31—H31A109.5
C9—C11—H11B109.5C29—C31—H31B109.5
H11A—C11—H11B109.5H31A—C31—H31B109.5
C9—C11—H11C109.5C29—C31—H31C109.5
H11A—C11—H11C109.5H31A—C31—H31C109.5
H11B—C11—H11C109.5H31B—C31—H31C109.5
C9—C12—H12A109.5C29—C32—H32A109.5
C9—C12—H12B109.5C29—C32—H32B109.5
H12A—C12—H12B109.5H32A—C32—H32B109.5
C9—C12—H12C109.5C29—C32—H32C109.5
H12A—C12—H12C109.5H32A—C32—H32C109.5
H12B—C12—H12C109.5H32B—C32—H32C109.5
C14—C13—C18119.1 (2)C38—C33—C34119.8 (2)
C14—C13—N2116.2 (2)C38—C33—N4115.74 (19)
C18—C13—N2124.7 (2)C34—C33—N4124.42 (19)
C13—C14—C15121.8 (2)C35—C34—C33120.5 (2)
C13—C14—H14119.1C35—C34—H34119.7
C15—C14—H14119.1C33—C34—H34119.7
C16—C15—C14118.5 (2)C34—C35—C36119.9 (2)
C16—C15—C19121.8 (2)C34—C35—C39119.7 (2)
C14—C15—C19119.7 (2)C36—C35—C39120.4 (2)
C17—C16—C15119.7 (2)C37—C36—C35119.0 (2)
C17—C16—C20120.0 (2)C37—C36—C40120.1 (2)
C15—C16—C20120.3 (2)C35—C36—C40120.9 (2)
C18—C17—C16121.6 (2)C38—C37—C36121.1 (2)
C18—C17—H17119.2C38—C37—H37119.5
C16—C17—H17119.2C36—C37—H37119.5
C17—C18—C13119.2 (2)C37—C38—C33119.7 (2)
C17—C18—H18120.4C37—C38—H38120.2
C13—C18—H18120.4C33—C38—H38120.2
C15—C19—H19A109.5C35—C39—H39A109.5
C15—C19—H19B109.5C35—C39—H39B109.5
H19A—C19—H19B109.5H39A—C39—H39B109.5
C15—C19—H19C109.5C35—C39—H39C109.5
H19A—C19—H19C109.5H39A—C39—H39C109.5
H19B—C19—H19C109.5H39B—C39—H39C109.5
C16—C20—H20A109.5C36—C40—H40A109.5
C16—C20—H20B109.5C36—C40—H40B109.5
H20A—C20—H20B109.5H40A—C40—H40B109.5
C16—C20—H20C109.5C36—C40—H40C109.5
H20A—C20—H20C109.5H40A—C40—H40C109.5
H20B—C20—H20C109.5H40B—C40—H40C109.5
C1—N1—N2—C13178.45 (17)C21—N3—N4—C33−176.50 (17)
N2—N1—C1—C2177.35 (19)N4—N3—C21—C22177.8 (2)
N2—N1—C1—C3−6.3 (3)N4—N3—C21—C23−0.2 (3)
N1—C1—C2—Br1179.63 (14)N3—C21—C22—Br4−2.6 (3)
C3—C1—C2—Br13.3 (3)C23—C21—C22—Br4175.41 (16)
N1—C1—C2—Br21.0 (3)N3—C21—C22—Br3178.31 (15)
C3—C1—C2—Br2−175.32 (15)C23—C21—C22—Br3−3.7 (3)
C2—C1—C3—C889.0 (3)C22—C21—C23—C28−64.6 (3)
N1—C1—C3—C8−87.1 (3)N3—C21—C23—C28113.2 (2)
C2—C1—C3—C4−93.1 (3)C22—C21—C23—C24115.3 (3)
N1—C1—C3—C490.7 (3)N3—C21—C23—C24−66.9 (3)
C8—C3—C4—C50.0 (3)C28—C23—C24—C250.6 (3)
C1—C3—C4—C5−177.83 (19)C21—C23—C24—C25−179.4 (2)
C3—C4—C5—C6−0.6 (3)C23—C24—C25—C26−0.5 (3)
C4—C5—C6—C70.6 (3)C24—C25—C26—C27−0.1 (3)
C4—C5—C6—C9−179.88 (19)C24—C25—C26—C29−179.4 (2)
C5—C6—C7—C80.0 (3)C25—C26—C27—C280.7 (3)
C9—C6—C7—C8−179.51 (19)C29—C26—C27—C28179.9 (2)
C4—C3—C8—C70.6 (3)C24—C23—C28—C270.0 (3)
C1—C3—C8—C7178.49 (19)C21—C23—C28—C27180.0 (2)
C6—C7—C8—C3−0.6 (3)C26—C27—C28—C23−0.7 (3)
C7—C6—C9—C11−124.5 (2)C27—C26—C29—C310.0 (3)
C5—C6—C9—C1156.0 (3)C25—C26—C29—C31179.2 (2)
C7—C6—C9—C10115.5 (2)C27—C26—C29—C32120.3 (2)
C5—C6—C9—C10−64.0 (2)C25—C26—C29—C32−60.5 (3)
C7—C6—C9—C12−4.3 (3)C27—C26—C29—C30−120.2 (2)
C5—C6—C9—C12176.27 (19)C25—C26—C29—C3059.0 (3)
N1—N2—C13—C14−179.04 (18)N3—N4—C33—C38179.90 (19)
N1—N2—C13—C180.2 (3)N3—N4—C33—C341.9 (3)
C18—C13—C14—C15−0.7 (3)C38—C33—C34—C35−1.6 (3)
N2—C13—C14—C15178.53 (19)N4—C33—C34—C35176.37 (19)
C13—C14—C15—C16−1.0 (3)C33—C34—C35—C36−0.2 (3)
C13—C14—C15—C19179.2 (2)C33—C34—C35—C39−178.9 (2)
C14—C15—C16—C172.3 (3)C34—C35—C36—C371.7 (3)
C19—C15—C16—C17−177.9 (2)C39—C35—C36—C37−179.6 (2)
C14—C15—C16—C20−177.3 (2)C34—C35—C36—C40−176.3 (2)
C19—C15—C16—C202.5 (3)C39—C35—C36—C402.4 (3)
C15—C16—C17—C18−1.9 (3)C35—C36—C37—C38−1.3 (3)
C20—C16—C17—C18177.7 (2)C40—C36—C37—C38176.7 (2)
C16—C17—C18—C130.1 (3)C36—C37—C38—C33−0.4 (3)
C14—C13—C18—C171.2 (3)C34—C33—C38—C371.9 (3)
N2—C13—C18—C17−178.0 (2)N4—C33—C38—C37−176.22 (19)
 

Acknowledgements

This paper was supported by Baku State University and Baku Engineering University, and the Vicerrectoría de Investigación y Desarrollo Tecnológico (VRIDT-UCN) and Dirección de Investigación y Análisis de la Producción Científica (DIAPC-UCN) of the Universidad Católica del Norte, Chile. The authors' contributions are as follows. Conceptualization, NGH and AMM; methodology, AAN and AMG; investigation, AMG and JC; writing (original draft), ANK, JC and NGS,; writing (review and editing of the manuscript), ANK, VNK and JC; visualization, JC, VNK and AB; funding acquisition, NGS, ANK and AB; resources, AAN and JC; supervision, ANK and NGH.

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ISSN: 2056-9890
Volume 81| Part 8| August 2025| Pages 662-666
https://doi.org/10.1107/S2056989025005390
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