Synthesis, crystal structure and Hirshfeld surface analysis of (2Z,2′E)-2,2′-(3-meth­oxy-3-phenylpropane-1,2-diyl­idene)bis­(hydrazine-1-carbo­thioamide) di­methyl­formamide monosolvate

Guseinov, F.I.; Knyazev, A.V.; Shuvalova, E.V.; Kobrakov, K.I.; Samigullina, A.I.; Atioğlu, Z.; Akkurt, M.; Bhattarai, A.

doi:10.1107/S2056989023007946

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ISSN: 2056-9890

Volume 79| Part 10| October 2023| Pages 910-915

https://doi.org/10.1107/S2056989023007946

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Synthesis, crystal structure and Hirshfeld surface analysis of (2Z,2′E)-2,2′-(3-methoxy-3-phenylpropane-1,2-diylidene)bis(hydrazine-1-carbothioamide) dimethylformamide monosolvate

Firudin I. Guseinov,^a,^b Aleksandr V. Knyazev,^b,^c Elena V. Shuvalova,^b Konstantin I. Kobrakov,^a Aida I. Samigullina,^b Zeliha Atioğlu,^d Mehmet Akkurt ^e ^* and Ajaya Bhattarai ^f ^*

^aKosygin State University of Russia, 117997 Moscow, Russian Federation, ^bN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation, ^cMIREA, Russian Technology University, Lomonosov Institute of Fine Chemical Technology, Moscow, 119571, Russian Federation, ^dDepartment of Aircraft Electrics and Electronics, School of Applied Sciences, Cappadocia University, Mustafapaşa, 50420 Ürgüp, Nevşehir, Türkiye, ^eDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, and ^fDepartment of Chemistry, M.M.A.M.C (Tribhuvan University), Biratnagar, Nepal
^*Correspondence e-mail: akkurt@erciyes.edu.tr, ajaya.bhattarai@mmamc.tu.edu.np

Edited by C. Schulzke, Universität Greifswald, Germany (Received 4 August 2023; accepted 11 September 2023; online 14 September 2023)

The overall molecular configuration of the title compound, C₁₂H₁₆N₆OS₂·C₃H₇NO, is stabilized in the solid state by intramolecular C—H⋯N, C—H⋯O, N—H⋯N and N—H⋯O interactions, forming S(5) ring motifs. In the crystal, molecules are linked to each other and solvent dimethylformamide molecules by N—H⋯S, N—H⋯O, C—H⋯O and C—H⋯S hydrogen bonds, forming a three dimensional network. The phenyl ring of the title compound is disordered over two sites with an occupancy ratio of 0.57 (4):0.43 (4). A Hirshfeld surface analysis was performed to quantify the contributions of the different intermolecular interactions, indicating that the most important contributions to the crystal packing are from H⋯H (38.7%), S⋯H / H⋯S (24.0%), C⋯H / H⋯C (18.5%) and N⋯H / H⋯N (9.8%) interactions.

Keywords: crystal structure; disorder; hydrogen bonds; Hirshfeld surface analysis; α-chloroketone; chlorooxirane; bisthiosemicarbazone.

CCDC reference: 2294475

1. Chemical context

Hydrazones are very attractive compounds in synthesis, catalysis, crystal engineering and medicinal chemistry due to their reactivity, hydrogen-bonding donor ability and broad spectrum of biological activities (Afkhami et al., 2019 ; Gurbanov et al., 2020a ,b ; Mahmoudi et al., 2017a ,b ,c ; Khalilov 2021 ; Martins et al., 2017 ). The most common synthetic pathway for the synthesis of hydrazones is the reaction of appropriate hydrazines with different aldehydes or ketones in various organic solvents (Khalilov et al., 2021 ). For example, hydrazinecarbothioamide has been well explored as a substrate in the synthesis of hydrazones (Safarova et al., 2019 ; Velásquez et al., 2019 ). The functional properties of hydrazones can be improved by attaching electron-withdrawing or -donating substituents to the hydrazone moiety (Gurbanov et al., 2022b , 2017 , 2021 ; Kopylovich et al., 2011 ). In fact, due to the participation of the substituents in various sorts of intermolecular interactions (Mahmudov et al., 2010 , 2012 , 2022 ; Mahmoudi et al., 2019 , 2021 ) the catalytic activity of metal complexes of hydrazones has been improved in comparison to those with unsubstituted ligands (Gurbanov et al., 2022a ). In order to continue our work in this perspective, we have synthesized a new hydrazone dimethylformamide monosolvate, (2Z,2′E)-2,2′-(3-methoxy-3-phenylpropane-1,2-diylidene)bis(hydrazine-1-carbothioamide)·DMF via reaction of hydrazinecarbothioamide with the highly reactive substrate 2-chloro-2-(diethoxymethyl)-3-phenyloxirane, which may be also replaced by 1-chloro-3,3-diethoxy-1-phenylpropan-2-one (Guseinov et al., 2006 , 2017 , 2020 ).

2. Structural commentary

As shown in Fig. 1, the title compound adopts a Z configuration about the C5=C6 double bond with regard to the 3-methoxy-3-phenylpropane group and E configuration regarding the hydrazine-1-carbothioamide moieties. The bond has a length of 1.452 (3) Å. The molecular conformation of the title compound is stabilized by intramolecular C11—H11⋯N7, C17—H17⋯O18, N1—H1A⋯N4 and N3—H3⋯O18 classical and non-classical hydrogen-bonding interactions, resulting in S(5) ring motifs (Table 1; Bernstein et al., 1995 ). The C12–C17 phenyl ring is disordered over two sites with occupancy factors in a 0.57 (4) to 0.43 (4) ratio. The major (C12–C17) and minor (C12A–C17A) components of the disordered phenyl ring subtend a dihedral angle of 2.0 (9)° to each other, i.e. they are nearly co-planar. Bond lengths and angles of the title compound are generally in agreement with those reported for related compounds, as discussed in the Database survey section below.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N4	0.92 (3)	2.27 (4)	2.670 (3)	106 (3)
N1—H1B⋯S9ⁱ	0.92 (4)	2.54 (4)	3.450 (2)	172 (4)
N3—H3⋯O18	0.90 (2)	2.04 (3)	2.694 (3)	129 (3)
N8—H8⋯O24ⁱⁱ	0.87 (3)	2.07 (4)	2.847 (4)	149 (3)
N10—H10A⋯S9ⁱⁱⁱ	0.91 (3)	2.72 (3)	3.570 (3)	156 (3)
N10—H10B⋯S2^iv	0.91 (4)	2.42 (4)	3.322 (3)	175 (4)
C6—H6⋯O24ⁱⁱ	0.95	2.54	3.224 (4)	129
C11—H11⋯N7	1.00	2.42	2.853 (3)	105
C11—H11⋯S9ⁱⁱⁱ	1.00	2.87	3.706 (2)	141
C17—H17⋯O18	0.95	2.45	2.787 (16)	101
C21—H21B⋯S9^v	0.98	2.98	3.951 (5)	171
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (v) $[x-1, -y+1, z-{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, showing the atom labeling and displacement ellipsoids drawn at the 30% probability level. Intramolecular C11—H11⋯N7, C17—H17⋯O18, N1—H1A⋯N4 and N3—H3⋯O18 interactions are shown as dashed lines. The minor component of the disorder was omitted for clarity reasons.

3. Supramolecular features and Hirshfeld surface analysis

Molecules in the crystal of the title compound are linked to each other and to the solvent dimethylformamide by classical and non-classical N—H⋯S, N—H⋯O, C—H⋯O and C—H⋯S hydrogen bonds (Table 1; Figs. 2, 3 and 4), resulting in a three-dimensional network. Fig. 5 shows all interactions as supplied in Table 1. In addition some offset weak C/N—H⋯π interactions are observed.

Figure 2
View of the molecular packing along the a-axis. Intramolecular C—H⋯N, C—H⋯O, N—H⋯N and N—H⋯O interactions and intermolecular N—H⋯S, N—H⋯O, C—H⋯O and C—H⋯S hydrogen bonds are shown as dashed lines. The minor part of the disorder and hydrogen atoms not involved in hydrogen bonding were omitted for clarity reasons.

Figure 3
View of the molecular packing along the b-axis. Intramolecular C—H⋯N, C—H⋯O, N—H⋯N and N—H⋯O interactions and intermolecular N—H⋯S, N—H⋯O, C—H⋯O and C—H⋯S hydrogen bonds are shown as dashed lines. The minor part of the disorder and hydrogen atoms not involved in hydrogen bonding were omitted for clarity reasons.

Figure 4
View of the molecular packing along the c-axis. Intramolecular C—H⋯N, C—H⋯O, N—H⋯N and N—H⋯O interactions and intermolecular N—H⋯S, N—H⋯O, C—H⋯O and C—H⋯S hydrogen bonds are shown as dashed lines. The minor part of the disorder and hydrogen atoms not involved in hydrogen bonding were omitted for clarity reasons.

Figure 5
A general view of the possible intra- and intermolecular hydrogen bonds of the molecule. The minor disorder component was omitted for clarity. Symmetry codes: (i) x − $[{1\over 2}]$ , y + $[{1\over 2}]$ , z; (ii) x, −y + 1, z + $[{1\over 2}]$ ; (iii) x, −y + 1, z − $[{1\over 2}]$ ; (iv) x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , z; (v) x − 1, −y + 1, z − $[{1\over 2}]$ .

Crystal Explorer 17.5 (Spackman et al., 2021 ) was used to perform a Hirshfeld surface analysis and to generate the corresponding two-dimensional fingerprint plots, with a standard resolution of the three-dimensional d_norm surfaces plotted over a fixed color scale of −0.5044 (red) to +1.5170 (blue) a.u. (Fig. 6). The red spots symbolize short contacts and negative d_norm values on the surface corresponding to the N—H⋯S, N—H⋯O and C—H⋯O hydrogen bonds mentioned above (Table 1). The N1—H1B⋯S9, N8—H8⋯O24, N10—H10A⋯S9, N10—H10B⋯S2 and C6—H6⋯O24 interactions, which play a key role in the molecular packing of the title compound, are responsible for the red spots observed around S2, S9 and O24.

Figure 6
(a) Front and (b) back sides of the three-dimensional Hirshfeld surface of the title compound mapped over d_norm.

The overall two-dimensional fingerprint plot for the title compound is provided in Fig. 7a, and those delineated into N—H⋯S, N—H⋯O and C—H⋯O contacts are shown in Fig. 7b–e, while numerical details of the different contacts are supplied in Table 2. The most important contributions to the Hirshfeld surfaces from the various interatomic contacts are H⋯H (38.7%), S⋯H / H⋯S (24.0%), C⋯H/H⋯C (18.5%) and N⋯H/H⋯N ((9.8%). Other, less notable contacts comprise O⋯H/H⋯O (5.0%), S⋯N/N⋯S (1.7%), S⋯C/C⋯S (0.7%), O⋯N/N⋯O (0.5%), N⋯C/C⋯N (0.4%), N⋯N (0.2%), C⋯C (0.2%) and S⋯O/O⋯S (0.1%); they have little, if any, directional influence on the molecular packing.

Table 2
Summary of short interatomic contacts (Å) in the title compound

Contact	Distance	Symmetry operation
S2⋯H10B	2.42	− $[{1\over 2}]$ + x, $[{1\over 2}]$ + y, z
H16⋯O24	2.73	$[{1\over 2}]$ + x, $[{1\over 2}]$ + y, z
H19A⋯N3	2.71	− $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z
S9⋯H10A	2.72	x, 1 − y, $[{1\over 2}]$ + z
S9⋯H21B	2.98	1 + x, 1 − y, $[{1\over 2}]$ + z
H6⋯H16A	2.49	− $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z
N3⋯H15A	2.56	−1 + x, y, z
H8⋯O24	2.07	x, 1 − y, $[{1\over 2}]$ + z
H19B⋯H22A	2.58	x, y, z
H22C⋯H21A	2.31	x, 1 − y, − $[{1\over 2}]$ + z

Figure 7
The two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and those delineated into (b) H⋯H, (c) S⋯H/H⋯S, (d) C⋯H/H⋯C and (e) N⋯H/H⋯N interactions. [d_e and d_i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (internal) the surface, respectively].

4. Database survey

A database search was carried out using ConQUEST (Bruno et al., 2002 ), part of the software for version 2023.2.0 of the Cambridge Structural Database (Groom et al., 2016 ). A search for the keyword `hydrazinecarbothioamide' resulted in nearly 600 hits. A search for the structural bis-hydrazinecarbothioamide motif without considering hydrogen atoms narrowed that down to 45. For a more detailed analysis, four of those compounds were chosen as relatively more closely related to the title compound, yet with a variation of the substituent(s) numbers and position on the bis-hydrazinecarbothioamide backbone. These are: (E,E)-N,N-dimethyl-2-{3-[(methylcarbamothioyl)hydrazono]butan-2-ylidene}hydrazinecarbothioamide (CD refcode ERABIJ; Paterson et al., 2010 ), diacetyl-2-(4-N-ethyl-3-thiosemicarbazone)-3-(4-N-allyl-3-thiosemicarbazone) dimethylsulfoxide solvate (JEXXOA; Holland et al., 2007 ), 2-keto-3-ethoxybutyraldehydebis(thiosemicarbazone) (KEBASC10; Gabe et al., 1969 ) and N,1-dimethyl-2-{3-[2-(methylcarbamothioyl)hydrazinylidene]butan-2-ylidene}hydrazine-1-carbothioamide (RECKAP; Alonso et al., 2022 ).

In the crystal of ERABIJ (monoclinic space group: P2₁/c, Z = 4), the molecule adopts an (E, E)-configuration about the imine double bonds. The arm bearing a dimethyl substituent has a slightly shorter C—S [1.6802 (19) Å] bond length and a longer C—N [1.341 (2) Å] bond length than the arm with a single methyl substituent [1.693 (2) and 1.323 (3) Å, respectively]. These bond lengths indicate that there is some extensive delocalization throughout the molecule while one tautomeric form still dominates.

In the crystal of JEXXOA (monoclinic space group: P2₁/c, Z = 2), the unsymmetrical bis(thiosemicarbazone) lies on a crystallographic center of inversion. The carbon–carbon bond length between C5 and C6 is 1.478 (3) Å, which is exactly the same as the average bond length expected for a single bond between two sp²-hybridized carbon atoms. Other bond lengths are indicative of the presence of a conjugated system here as well.

In the crystal of KEBASC10 (monoclinic space group: P2₁/c, Z = 8), there are two molecules per asymmetric unit. The bis-hydrazinecarbothioamide motif is outstretched (i.e. not bent) and extends from one sulfur atom to the other as head and tail atoms. The molecule is approximately planar except for the side chain. The bond distances and angles are very similar in the two molecules of the asymmetric unit. There is an intramolecular N—H⋯O hydrogen bond, which stabilizes the molecular structure, similar to what is observed in the title compound. The packing of the molecule seems dominated by the formation of N—H⋯S hydrogen bonds. There is also one very short C—H⋯S intermolecular distance between the two molecules in the asymmetric unit, which may be strong enough to cause some distortion, in one molecule more than in the other. The tendency of molecules that are crystallographically independent but have opposite absolute configurations to associate may explain why they have co-crystallized in this case and why there are, hence, two independent molecules in the asymmetric unit.

In the crystal of RECKAP (triclinic space group: P $[\overline{1}]$ , Z = 2), the compound is in the thione form yet resonant, which is supported by the C—S bond distances, which are intermediate between those of single and double bonds (1.82 and 1.56 Å, respectively) and the presence of the hydrazinic hydrogen H2. The azomethine bonds both have a length of 1.29 Å, which is in accordance with double bonds. The N—N bonds are both shorter than 1.44 Å, which agrees well with those of similar thiosemicarbazones. The two arms of the molecule adopt the E configuration with respect to the central C3—C4 single bond and both azomethine nitrogen atoms N3 and N4 are in an E configuration relative to the thione sulfur atoms. The ligand is not planar and the two arms form an angle of 73.51°. The molecules are held together in the crystal through an extended network of intermolecular hydrogen bonds involving the amine nitrogen atoms N1 and N6 and the sulfur atoms.

All the molecules discussed here, including the title compound, adopt an E configuration of the hydrazine moieties attached to the central C—C bond. The differences in substitution do not affect this. However, the latter gives rise to a variation in the intermolecular interactions and can also result in distinct molecular shapes from the more common (almost) planar arrangement of the bis-hydrazinecarbothioamide motif to a substantial twisting to nearly perpendicular.

5. Synthesis and crystallization

Hydrazinecarbothioamide (0.380 g, 6.25 mmol) and 2-chloro-2-(diethoxymethyl)-3-phenyloxirane (1.600 g, 6.25 mmol) in 20 mL of methanol was refluxed for 2 h. After complete dissolution of hydrazinecarbothioamide, the mixture was stirred at room temperature for 24 h. The progress of the reaction was monitored by TLC in the system 9:1 chloroform:methanol R_f = 0.53. After completion of the reaction, the solvent was evaporated. The title compound was isolated by column chromatography in a 20:1 chloroform:methanol R_f = 0.17 system. The compound was obtained as a white solid in a yield of 0.689 g (34%); m.p. 421–423 K (with decomposition). Analysis calculated for C₁₂H₁₆N₆OS₂ (M = 324.42) C 44.43, H 4.97, N 25.91; found: C 44.35, H 4.90, N 25.94. ¹H NMR (300 MHz, DMSO-d₆) δ 3.52 (3H, CH₃), 6.35 (1H, CH), 7.37–7.45 (5H, Ar), 8,15–8.68 (2H, NH), 10.74 (2H, NH₂), 10.80 (s, 2H, NH₂). ¹³C NMR (200 MHz, DMSO-d₆) δ 57.13, 78.52, 126.22, 128.45, 136.79, 138.92, 144.20, 177.67, 178.18. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of the DMF:methanol solution.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The C12(C12A)–C17(C17A) atoms in the C12–C17 phenyl ring are disordered over two sites with occupancies of 0.57 (4) and 0.43 (4), respectively. The N-bound hydrogen atoms were located in difference maps [N1—H1A = 0.92 (2), N1—H1B = 0.92 (2), N3—H3 = 0.90 (2), N8—H8 = 0.88 (2), N10—H10A = 0.91 (2) and N10—H10B = 0.90 (2) Å] and refined by constraining the N—H distances with SADI. All carbon-bound hydrogen atoms were positioned geometrically (C—H = 0.95–1.00 Å) and were included in the refinement in the riding-model approximation with U_iso(H) = 1.2 or 1.5U_eq(C).

Table 3
Experimental details

Crystal data
Chemical formula	C₁₂H₁₆N₆OS₂·C₃H₇NO
M_r	397.52
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	8.4573 (1), 23.5853 (3), 11.0072 (1)
β (°)	111.749 (2)
V (Å³)	2039.29 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	2.57
Crystal size (mm)	0.32 × 0.12 × 0.02

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2023 $[Rigaku OD (2023). CrysAlis PRO 1.171.42.91a. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.658, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11141, 2776, 2751
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.088, 1.07
No. of reflections	2776
No. of parameters	317
No. of restraints	377
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.27
Absolute structure	Classical Flack method preferred over Parsons because s.u. lower
Absolute structure parameter	0.000 (16)
Computer programs: CrysAlis PRO (Rigaku OD, 2023 $[Rigaku OD (2023). CrysAlis PRO 1.171.42.91a. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2019/1 (Sheldrick, 2015a ), SHELXL2019/1 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2294475

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989023007946/yz2041sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023007946/yz2041Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO 1.171.42.91a (Rigaku OD, 2023); cell refinement: CrysAlis PRO 1.171.42.91a (Rigaku OD, 2023); data reduction: CrysAlis PRO 1.171.42.91a (Rigaku OD, 2023); program(s) used to solve structure: SHELXT2019/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/1 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

\ (2Z,2'E)-2,2'-(3-Methoxy-3-phenylpropane-1,2-diylidene)\ bis(2-methylhydrazine-1-carbothioamide) dimethylformamide monosolvate top

Crystal data top

C₁₂H₁₆N₆OS₂·C₃H₇NO	F(000) = 840
M_r = 397.52	D_x = 1.295 Mg m⁻³
Monoclinic, Cc	Cu Kα radiation, λ = 1.54184 Å
a = 8.4573 (1) Å	Cell parameters from 9940 reflections
b = 23.5853 (3) Å	θ = 3.7–77.6°
c = 11.0072 (1) Å	µ = 2.57 mm⁻¹
β = 111.749 (2)°	T = 100 K
V = 2039.29 (5) Å³	Plate, colourless
Z = 4	0.32 × 0.12 × 0.02 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	2776 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2751 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
ω scans	θ_max = 77.8°, θ_min = 3.8°
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2023)	h = −10→10
T_min = 0.658, T_max = 1.000	k = −29→29
11141 measured reflections	l = −9→13

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0653P)² + 0.7217P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.088	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.30 e Å⁻³
2776 reflections	Δρ_min = −0.27 e Å⁻³
317 parameters	Absolute structure: Classical Flack method preferred over Parsons because s.u. lower
377 restraints	Absolute structure parameter: 0.000 (16)

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)
S2	0.28482 (9)	0.88049 (2)	0.35678 (8)	0.02715 (16)
S9	0.62361 (9)	0.43859 (2)	0.67836 (8)	0.02788 (17)
O18	0.3029 (2)	0.69867 (7)	0.22627 (17)	0.0208 (4)
N1	0.3182 (3)	0.82853 (9)	0.5810 (2)	0.0250 (4)
H1A	0.321 (5)	0.7946 (11)	0.623 (4)	0.035 (10)*
H1B	0.277 (5)	0.8600 (14)	0.609 (4)	0.050 (12)*
N3	0.3551 (3)	0.77463 (9)	0.4201 (2)	0.0193 (4)
H3	0.338 (4)	0.7707 (16)	0.335 (2)	0.030 (9)*
N4	0.3832 (3)	0.72789 (9)	0.4985 (2)	0.0194 (4)
N7	0.5105 (3)	0.58678 (9)	0.5112 (2)	0.0206 (4)
N8	0.5322 (3)	0.54302 (9)	0.5966 (2)	0.0237 (4)
H8	0.494 (4)	0.5441 (15)	0.660 (3)	0.025 (8)*
N10	0.6502 (3)	0.49254 (10)	0.4741 (3)	0.0304 (5)
H10A	0.637 (4)	0.5197 (13)	0.412 (3)	0.028 (8)*
H10B	0.689 (5)	0.4610 (13)	0.447 (4)	0.042 (10)*
C2	0.3196 (3)	0.82596 (10)	0.4617 (3)	0.0196 (5)
C5	0.4275 (3)	0.68202 (10)	0.4549 (2)	0.0178 (5)
C6	0.4552 (3)	0.63348 (11)	0.5415 (3)	0.0211 (5)
H6	0.432845	0.636140	0.619743	0.025*
C9	0.6017 (3)	0.49391 (11)	0.5749 (3)	0.0245 (5)
C11	0.4518 (3)	0.67600 (10)	0.3245 (2)	0.0180 (4)
H11	0.462814	0.634948	0.306311	0.022*
C12	0.6115 (14)	0.7087 (7)	0.3235 (18)	0.017 (2)	0.57 (4)
C13	0.7717 (16)	0.6857 (6)	0.3961 (17)	0.019 (2)	0.57 (4)
H13	0.781040	0.650478	0.440053	0.023*	0.57 (4)
C14	0.9181 (14)	0.7156 (8)	0.4026 (14)	0.025 (2)	0.57 (4)
H14	1.027777	0.700727	0.451350	0.030*	0.57 (4)
C15	0.9025 (17)	0.7670 (7)	0.3378 (13)	0.024 (2)	0.57 (4)
H15	1.001690	0.787616	0.343977	0.029*	0.57 (4)
C16	0.7452 (17)	0.7882 (6)	0.2650 (14)	0.0204 (19)	0.57 (4)
H16	0.736384	0.822536	0.217843	0.025*	0.57 (4)
C17	0.5977 (16)	0.7599 (7)	0.2590 (16)	0.0155 (19)	0.57 (4)
H17	0.488928	0.775672	0.211265	0.019*	0.57 (4)
C12A	0.618 (2)	0.7024 (9)	0.339 (2)	0.017 (3)	0.43 (4)
C13A	0.771 (2)	0.6743 (9)	0.411 (2)	0.022 (3)	0.43 (4)
H13A	0.769780	0.639161	0.452901	0.026*	0.43 (4)
C14A	0.9259 (19)	0.6998 (9)	0.4195 (19)	0.023 (2)	0.43 (4)
H14A	1.030313	0.681309	0.467394	0.027*	0.43 (4)
C15A	0.9282 (19)	0.7516 (9)	0.3588 (17)	0.020 (2)	0.43 (4)
H15A	1.033708	0.767984	0.365263	0.025*	0.43 (4)
C16A	0.780 (2)	0.7788 (8)	0.290 (2)	0.023 (3)	0.43 (4)
H16A	0.781356	0.814671	0.251521	0.028*	0.43 (4)
C17A	0.625 (2)	0.7534 (9)	0.277 (2)	0.021 (3)	0.43 (4)
H17A	0.521200	0.771477	0.225499	0.025*	0.43 (4)
C19	0.2808 (3)	0.67848 (12)	0.0984 (3)	0.0257 (5)
H19A	0.191339	0.700524	0.032715	0.039*
H19B	0.248038	0.638391	0.091007	0.039*
H19C	0.387790	0.682681	0.084046	0.039*
O24	0.2984 (3)	0.43619 (10)	0.2226 (3)	0.0449 (6)
N20	0.1627 (4)	0.49731 (13)	0.3120 (3)	0.0405 (6)
C21	0.0784 (5)	0.50587 (19)	0.4044 (5)	0.0551 (10)
H21A	0.075716	0.469985	0.448488	0.083*
H21B	−0.038264	0.519122	0.357418	0.083*
H21C	0.140992	0.534251	0.469463	0.083*
C22	0.1605 (5)	0.54375 (17)	0.2284 (4)	0.0503 (9)
H22A	0.259076	0.541176	0.202153	0.075*
H22B	0.165269	0.579467	0.275069	0.075*
H22C	0.055571	0.542499	0.150377	0.075*
C23	0.2273 (5)	0.44708 (17)	0.3000 (4)	0.0456 (8)
H23	0.218115	0.417283	0.355074	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S2	0.0435 (3)	0.0159 (3)	0.0262 (3)	0.0076 (2)	0.0178 (3)	0.0043 (2)
S9	0.0488 (3)	0.0145 (3)	0.0281 (3)	0.0061 (2)	0.0234 (3)	0.0048 (2)
O18	0.0219 (7)	0.0219 (8)	0.0180 (9)	0.0023 (7)	0.0067 (6)	0.0003 (7)
N1	0.0383 (11)	0.0165 (9)	0.0250 (11)	0.0039 (8)	0.0172 (9)	0.0016 (9)
N3	0.0264 (9)	0.0145 (9)	0.0198 (10)	0.0028 (7)	0.0117 (8)	0.0030 (8)
N4	0.0233 (8)	0.0140 (9)	0.0230 (10)	0.0021 (7)	0.0112 (8)	0.0016 (8)
N7	0.0298 (9)	0.0144 (9)	0.0200 (10)	0.0022 (8)	0.0120 (8)	0.0017 (8)
N8	0.0390 (11)	0.0148 (10)	0.0236 (11)	0.0044 (9)	0.0191 (9)	0.0029 (9)
N10	0.0538 (14)	0.0157 (10)	0.0324 (13)	0.0092 (10)	0.0287 (11)	0.0052 (9)
C2	0.0205 (9)	0.0158 (11)	0.0232 (12)	0.0015 (8)	0.0090 (9)	−0.0009 (9)
C5	0.0221 (10)	0.0135 (10)	0.0192 (11)	0.0007 (8)	0.0093 (9)	0.0007 (8)
C6	0.0307 (11)	0.0158 (11)	0.0208 (11)	0.0010 (9)	0.0141 (9)	0.0012 (10)
C9	0.0345 (12)	0.0169 (12)	0.0248 (12)	0.0016 (9)	0.0141 (10)	0.0011 (10)
C11	0.0199 (9)	0.0165 (10)	0.0186 (11)	0.0023 (8)	0.0081 (8)	0.0007 (9)
C12	0.014 (3)	0.023 (5)	0.013 (4)	−0.002 (3)	0.005 (2)	0.002 (3)
C13	0.028 (3)	0.015 (4)	0.017 (4)	0.001 (2)	0.011 (2)	0.007 (3)
C14	0.020 (2)	0.031 (5)	0.023 (4)	0.004 (3)	0.007 (2)	0.004 (4)
C15	0.025 (4)	0.025 (5)	0.024 (4)	0.000 (3)	0.011 (3)	0.003 (3)
C16	0.025 (4)	0.021 (4)	0.017 (4)	−0.002 (3)	0.009 (3)	0.002 (3)
C17	0.019 (3)	0.016 (4)	0.013 (4)	0.000 (3)	0.008 (3)	0.004 (2)
C12A	0.033 (5)	0.013 (4)	0.011 (5)	0.004 (3)	0.014 (3)	0.000 (3)
C13A	0.019 (3)	0.028 (6)	0.020 (5)	0.004 (3)	0.008 (3)	0.005 (4)
C14A	0.023 (3)	0.025 (6)	0.021 (5)	0.003 (4)	0.008 (3)	0.004 (4)
C15A	0.018 (3)	0.022 (6)	0.020 (5)	0.002 (4)	0.006 (3)	−0.004 (4)
C16A	0.030 (5)	0.021 (5)	0.018 (5)	−0.004 (4)	0.009 (4)	0.003 (4)
C17A	0.022 (4)	0.020 (5)	0.019 (6)	0.008 (4)	0.006 (4)	0.001 (4)
C19	0.0297 (11)	0.0270 (13)	0.0184 (12)	0.0000 (10)	0.0065 (10)	−0.0003 (10)
O24	0.0539 (13)	0.0453 (14)	0.0487 (15)	0.0031 (11)	0.0343 (12)	0.0024 (11)
N20	0.0429 (13)	0.0399 (15)	0.0428 (16)	−0.0030 (11)	0.0206 (12)	−0.0034 (13)
C21	0.056 (2)	0.060 (2)	0.060 (3)	−0.0086 (19)	0.0335 (19)	−0.013 (2)
C22	0.0547 (19)	0.0407 (18)	0.059 (2)	−0.0030 (16)	0.0248 (17)	0.0019 (18)
C23	0.0524 (18)	0.0432 (18)	0.050 (2)	−0.0031 (15)	0.0299 (17)	−0.0010 (16)

Geometric parameters (Å, º) top

S2—C2	1.680 (3)	C15—C16	1.368 (9)
S9—C9	1.697 (3)	C15—H15	0.9500
O18—C11	1.426 (3)	C16—C17	1.394 (9)
O18—C19	1.430 (3)	C16—H16	0.9500
N1—C2	1.319 (4)	C17—H17	0.9500
N1—H1A	0.92 (2)	C12A—C17A	1.390 (14)
N1—H1B	0.92 (2)	C12A—C13A	1.407 (13)
N3—N4	1.365 (3)	C13A—C14A	1.413 (13)
N3—C2	1.366 (3)	C13A—H13A	0.9500
N3—H3	0.90 (2)	C14A—C15A	1.398 (12)
N4—C5	1.294 (3)	C14A—H14A	0.9500
N7—C6	1.288 (3)	C15A—C16A	1.361 (12)
N7—N8	1.362 (3)	C15A—H15A	0.9500
N8—C9	1.360 (3)	C16A—C17A	1.401 (13)
N8—H8	0.88 (2)	C16A—H16A	0.9500
N10—C9	1.318 (4)	C17A—H17A	0.9500
N10—H10A	0.91 (2)	C19—H19A	0.9800
N10—H10B	0.90 (2)	C19—H19B	0.9800
C5—C6	1.452 (3)	C19—H19C	0.9800
C5—C11	1.530 (3)	O24—C23	1.238 (4)
C6—H6	0.9500	N20—C23	1.332 (5)
C11—C12A	1.492 (19)	N20—C22	1.426 (5)
C11—C12	1.558 (13)	N20—C21	1.456 (5)
C11—H11	1.0000	C21—H21A	0.9800
C12—C17	1.384 (10)	C21—H21B	0.9800
C12—C13	1.402 (10)	C21—H21C	0.9800
C13—C14	1.404 (10)	C22—H22A	0.9800
C13—H13	0.9500	C22—H22B	0.9800
C14—C15	1.387 (9)	C22—H22C	0.9800
C14—H14	0.9500	C23—H23	0.9500

C11—O18—C19	112.21 (18)	C15—C16—H16	119.6
C2—N1—H1A	117 (3)	C17—C16—H16	119.6
C2—N1—H1B	121 (3)	C12—C17—C16	119.3 (8)
H1A—N1—H1B	119 (4)	C12—C17—H17	120.3
N4—N3—C2	120.8 (2)	C16—C17—H17	120.3
N4—N3—H3	120 (2)	C17A—C12A—C13A	119.3 (13)
C2—N3—H3	118 (2)	C17A—C12A—C11	121.0 (13)
C5—N4—N3	116.6 (2)	C13A—C12A—C11	119.7 (13)
C6—N7—N8	116.0 (2)	C12A—C13A—C14A	118.2 (12)
C9—N8—N7	118.7 (2)	C12A—C13A—H13A	120.9
C9—N8—H8	119 (2)	C14A—C13A—H13A	120.9
N7—N8—H8	123 (2)	C15A—C14A—C13A	121.2 (10)
C9—N10—H10A	128 (2)	C15A—C14A—H14A	119.4
C9—N10—H10B	124 (3)	C13A—C14A—H14A	119.4
H10A—N10—H10B	107 (4)	C16A—C15A—C14A	120.2 (10)
N1—C2—N3	117.3 (2)	C16A—C15A—H15A	119.9
N1—C2—S2	125.8 (2)	C14A—C15A—H15A	119.9
N3—C2—S2	116.9 (2)	C15A—C16A—C17A	119.5 (11)
N4—C5—C6	114.5 (2)	C15A—C16A—H16A	120.3
N4—C5—C11	125.7 (2)	C17A—C16A—H16A	120.3
C6—C5—C11	119.8 (2)	C12A—C17A—C16A	121.7 (12)
N7—C6—C5	119.3 (2)	C12A—C17A—H17A	119.2
N7—C6—H6	120.3	C16A—C17A—H17A	119.2
C5—C6—H6	120.3	O18—C19—H19A	109.5
N10—C9—N8	117.3 (2)	O18—C19—H19B	109.5
N10—C9—S9	123.8 (2)	H19A—C19—H19B	109.5
N8—C9—S9	118.9 (2)	O18—C19—H19C	109.5
O18—C11—C12A	117.2 (9)	H19A—C19—H19C	109.5
O18—C11—C5	106.77 (19)	H19B—C19—H19C	109.5
C12A—C11—C5	108.1 (10)	C23—N20—C22	121.8 (3)
O18—C11—C12	109.5 (6)	C23—N20—C21	121.2 (3)
C5—C11—C12	112.3 (8)	C22—N20—C21	116.8 (3)
O18—C11—H11	109.4	N20—C21—H21A	109.5
C5—C11—H11	109.4	N20—C21—H21B	109.5
C12—C11—H11	109.4	H21A—C21—H21B	109.5
C17—C12—C13	120.6 (9)	N20—C21—H21C	109.5
C17—C12—C11	121.8 (9)	H21A—C21—H21C	109.5
C13—C12—C11	117.5 (9)	H21B—C21—H21C	109.5
C12—C13—C14	118.9 (8)	N20—C22—H22A	109.5
C12—C13—H13	120.6	N20—C22—H22B	109.5
C14—C13—H13	120.6	H22A—C22—H22B	109.5
C15—C14—C13	119.9 (8)	N20—C22—H22C	109.5
C15—C14—H14	120.1	H22A—C22—H22C	109.5
C13—C14—H14	120.1	H22B—C22—H22C	109.5
C16—C15—C14	120.5 (8)	O24—C23—N20	125.1 (4)
C16—C15—H15	119.8	O24—C23—H23	117.5
C14—C15—H15	119.8	N20—C23—H23	117.5
C15—C16—C17	120.8 (8)

C2—N3—N4—C5	−175.4 (2)	C5—C11—C12—C13	73.3 (16)
C6—N7—N8—C9	−175.4 (2)	C17—C12—C13—C14	0 (3)
N4—N3—C2—N1	1.7 (3)	C11—C12—C13—C14	−176.8 (14)
N4—N3—C2—S2	−179.27 (16)	C12—C13—C14—C15	0 (2)
N3—N4—C5—C6	−179.78 (19)	C13—C14—C15—C16	−1.5 (19)
N3—N4—C5—C11	0.4 (3)	C14—C15—C16—C17	2.8 (19)
N8—N7—C6—C5	−179.5 (2)	C13—C12—C17—C16	1 (3)
N4—C5—C6—N7	−175.5 (2)	C11—C12—C17—C16	178.0 (14)
C11—C5—C6—N7	4.3 (3)	C15—C16—C17—C12	−3 (2)
N7—N8—C9—N10	2.6 (4)	O18—C11—C12A—C17A	12 (2)
N7—N8—C9—S9	−178.22 (17)	C5—C11—C12A—C17A	−109 (2)
C19—O18—C11—C12A	79.2 (11)	O18—C11—C12A—C13A	−165.2 (16)
C19—O18—C11—C5	−159.5 (2)	C5—C11—C12A—C13A	74 (2)
C19—O18—C11—C12	78.8 (8)	C17A—C12A—C13A—C14A	1 (3)
N4—C5—C11—O18	−50.3 (3)	C11—C12A—C13A—C14A	178.2 (18)
C6—C5—C11—O18	129.9 (2)	C12A—C13A—C14A—C15A	0 (3)
N4—C5—C11—C12A	76.6 (9)	C13A—C14A—C15A—C16A	0 (2)
C6—C5—C11—C12A	−103.2 (9)	C14A—C15A—C16A—C17A	−2 (2)
N4—C5—C11—C12	69.6 (6)	C13A—C12A—C17A—C16A	−3 (4)
C6—C5—C11—C12	−110.1 (6)	C11—C12A—C17A—C16A	179.8 (19)
O18—C11—C12—C17	14.8 (19)	C15A—C16A—C17A—C12A	4 (3)
C5—C11—C12—C17	−103.6 (16)	C22—N20—C23—O24	4.0 (6)
O18—C11—C12—C13	−168.3 (13)	C21—N20—C23—O24	178.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4	0.92 (3)	2.27 (4)	2.670 (3)	106 (3)
N1—H1B···S9ⁱ	0.92 (4)	2.54 (4)	3.450 (2)	172 (4)
N3—H3···O18	0.90 (2)	2.04 (3)	2.694 (3)	129 (3)
N8—H8···O24ⁱⁱ	0.87 (3)	2.07 (4)	2.847 (4)	149 (3)
N10—H10A···S9ⁱⁱⁱ	0.91 (3)	2.72 (3)	3.570 (3)	156 (3)
N10—H10B···S2^iv	0.91 (4)	2.42 (4)	3.322 (3)	175 (4)
C6—H6···O24ⁱⁱ	0.95	2.54	3.224 (4)	129
C11—H11···N7	1.00	2.42	2.853 (3)	105
C11—H11···S9ⁱⁱⁱ	1.00	2.87	3.706 (2)	141
C17—H17···O18	0.95	2.45	2.787 (16)	101
C21—H21B···S9^v	0.98	2.98	3.951 (5)	171

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

Summary of short interatomic contacts (Å) in the title compound top

Contact	Distance	Symmetry operation
S2···H10B	2.42	-1/2 + x, 1/2 + y, z
H16···O24	2.73	1/2 + x, 1/2 + y, z
H19A···N3	2.71	-1/2 + x, 3/2 - y, -1/2 + z
S9···H10A	2.72	x, 1 - y, 1/2 + z
S9···H21B	2.98	1 + x, 1 - y, 1/2 + z
H6···H16A	2.49	-1/2 + x, 3/2 - y, 1/2 + z
N3···H15A	2.56	-1 + x, y, z
H8···O24	2.07	x, 1 - y, 1/2 + z
H19B···H22A	2.58	x, y, z
H22C···H21A	2.31	x, 1 - y, -1/2 + z

Acknowledgements

The authors' contributions are as follows. Conceptualization, FIG, MA and AB; synthesis, AVK, EVS and KIK; X-ray analysis, AIS and ZA; writing (review and editing of the manuscript) FIG, MA and AB; supervision, FIG, MA and AB.

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