Crystal structure and Hirshfeld surface analysis of bis­{(Z)-N′-[(E)-(furan-2-yl)methyl­idene]carbamo­hydrazono­thio­ato}nickel(II) methanol disolvate

Azizova, A.N.; Mammadova, G.Z.; Çelikesir, S.T.; Akkurt, M.; Bhattarai, A.

doi:10.1107/S2056989023005182

research communications

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ISSN: 2056-9890

Volume 79| Part 7| July 2023| Pages 669-673

https://doi.org/10.1107/S2056989023005182

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Crystal structure and Hirshfeld surface analysis of bis{(Z)-N′-[(E)-(furan-2-yl)methylidene]carbamohydrazonothioato}nickel(II) methanol disolvate

Asmet N. Azizova,^a Gunay Z. Mammadova,^b Sevim Türktekin Çelikesir,^c Mehmet Akkurt ^c and Ajaya Bhattarai ^d ^*

^aDepartment of Synthesis of Biologically Active Compounds, Scientific Research Center, Azerbaijan Medical University, Samed Vurgun St. 167, Az 1022 Baku, Azerbaijan, ^bOrganic Chemistry Department, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, and ^dDepartment of Chemistry, M.M.A.M.C (Tribhuvan University), Biratnagar, Nepal
^*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np

Edited by J. Reibenspies, Texas A & M University, USA (Received 22 May 2023; accepted 10 June 2023; online 30 June 2023)

In the title complex, [Ni(C₆H₆N₃OS)₂]·2CH₃OH, the Ni^II atom is coordinated by the S and N atoms of two N′-[(Z)-(furan-2-yl)methylidene]carbamohydrazonothioic acid ligands in a distorted square-planar geometry. The two mutual ligands bound to Ni^II are also connected by C—H⋯S interactions, while the H atoms of the NH₂ group of the ligands form R⁴₄(8) motifs with the O atoms of the solvent ethyl alcohol molecules. At the same time, the OH groups of the solvent ethyl alcohol molecules form parallel layers to the (011) plane by the O—H⋯N interactions with the ligand N atom that is not bonded to the Ni^II atom.. The layers are connected by van der Waals interactions. A Hirshfeld surface analysis indicates that the most important contacts are H⋯H (37.7%), C⋯H/H⋯C (14.6%), O⋯H/H⋯O (11.5%) and S⋯H/H⋯S (10.6%).

Keywords: crystal structure; ligands; distorted square-planar geometry; hydrogen bonds; Hirshfeld surface analysis.

CCDC reference: 2269284

1. Chemical context

Hydrazones have been used extensively as substrates in organic synthesis (Polyanskii et al., 2019 ; Shikhaliyev et al., 2019 ; Safavora et al., 2019 ; Zubkov et al., 2018 ) and multidentate ligands (Gurbanov et al., 2020a ,b ; Gurbanov et al., 2022 ) while their complexes have been found to possess a wide variety of useful properties. Thus, they can be used as sensor or analytical reagents, catalysts and building blocks in crystal engineering (Ma et al., 2021 ; Mahmudov et al., 2010 ; Mahmoudi et al., 2017a ,b ). Not only because of their coordination ability, but also the attached substituents, the intermolecular non-covalent interactions direct the functional properties as well as the supramolecular chemistry of hydrazones (Abdelhamid et al., 2011 ; Khalilov et al., 2021 ; Kopylovich et al., 2011 ; Mahmudov et al., 2015 ;). In fact, hydrogen and chalcogen bonds and other types of weak interactions have been well employed in the decoration of the secondary coordination sphere of transition-metal complexes (Mahmoudi et al., 2019 ; Mahmudov et al., 2012 , 2022 ). We have synthesized a new Ni^II complex of a (E)-2-(furan-2-ylmethylene)hydrazine-1-carbothioamide ligand and studied its crystal structure.

2. Structural commentary

Fig. 1 shows the arrangement of the complex molecules in the unit cell. The Ni^II atom is coordinated by the S and N atoms of two N′-[(Z)-(furan-2-yl)methylidene]carbamohydrazonothioic acid ligands in a distorted square-planar geometry. The ligands assume a trans arrangement with respect to each other around the Ni^II ion, which lies on a crystallographic inversion centre at (−x + 1, −y, −z + 1). The Ni—S [2.1818 (6) Å] and Ni—N [1.9055 (17) Å] bond lengths lie within the range of those found in related structures.

Figure 1
The molecular structure of the title compound, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, the two mutual ligands bound to Ni^II are also linked by C—H⋯S interactions, while the H atoms of the NH₂ group of the ligands form R₄⁴(8) motifs (Bernstein et al., 1995 ; Tables 1 and 2; Fig. 2) with the O atoms of the solvent ethyl alcohol molecules. At the same time, the OH groups of the solvent ethyl alcohol molecules form parallel layers to the (011) plane by the O—H⋯N interactions with the ligand N atom that is not bonded to the Ni^II atom (Figs. 2, 3 and 4). These layers are connected by van der Waals interactions.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N2	0.90	1.94	2.788 (3)	156
N3—H3A⋯O2ⁱ	0.90	2.07	2.964 (3)	173
N3—H3B⋯O2ⁱⁱ	0.90	2.12	3.009 (3)	171
C5—H5⋯S1ⁱⁱⁱ	0.93	2.51	3.102 (3)	121
Symmetry codes: (i) ; (ii) ; (iii) .

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

Contact	Distance	Symmetry operation
S1⋯C5	3.55	−1 + x, y, z
H2⋯O1	2.78	2 − x, 1 − y, 1 − z
N2⋯H2O	1.94	x, y, z
H3B⋯O2	2.12	−1 + x, y, z
H3A⋯O2	2.07	1 − x, 1 − y, 1 − z
C1⋯C1	3.51	1 − x, 1 − y, 1 − z
H3B⋯H3A	2.55	−x, 1 − y, −z
H7C⋯H7C	2.38	2 − x, −y, −z

Figure 2
A view along the a axis of the crystal packing of the title compound. The O—H⋯N, N—H⋯O and C—H⋯S hydrogen bonds are shown as dashed lines.

Figure 3
A view along the b axis of the crystal packing of the title compound, with hydrogen bonds indicated by dashed lines.

Figure 4
A view along the c axis of the crystal packing of the title compound, with hydrogen bonds indicated by dashed lines.

A Hirshfeld surface analysis was carried out using CrystalExplorer 17.5 (Spackman et al., 2021 ) to analyse the intermolecular interactions. The three-dimensional Hirshfeld surface mapped over the normalized contact distance (d_norm) is shown in Fig. 5. The bright-red spots indicate shortened contacts, and correspond to the O—H⋯N and N—H⋯O intermolecular hydrogen bonds.

Figure 5
(a) Front and (b) back sides of the three-dimensional Hirshfeld surface of the title compound mapped over d_norm.

The two-dimensional fingerprint plots show the H⋯H (Fig. 6b; 37.7%) contacts to be the most common, followed by C⋯H/H⋯C (Fig. 6c; 14.6%), O⋯H/H⋯O (Fig. 6d; 11.5%) and S⋯H/H⋯S (Fig. 6e; 10.6%) contacts. The N⋯H/H⋯N (8.5%), O⋯C/C⋯O (4.9%), Ni⋯H/H⋯Ni (3.2%), O⋯N/N⋯O (2.2%), N⋯C/C⋯N (1.9%), C⋯C (1.8%), S⋯C/C⋯S (1.1%), S⋯S (0.7%), O⋯O (0.7%),S⋯O/O⋯S (0.5%) and Ni⋯C/C⋯Ni (0.2%) contacts have little directional influence on the molecular packing.

Figure 6
The two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) O⋯H/H⋯O and (e) S⋯H/H⋯S 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 search of the Cambridge Structural Database (ConQUEST version 2022 3.0; Groom et al., 2016 ) for one of the Ni atoms plus ligands in the title compound yielded 14 structures that have the same framework as the title compound. FUTRAN (Puranik et al., 1987 ) appears to be the same structure, without any solvent, and NOQCUS (Rodríguez-Argüelles et al., 2009 ) is the same with a dimethyl sulfoxide solvent molecule; the other 12 have alkyl or phenyl groups attached.

In the crystal of FUTRAN, Ni ^II is in the distorted square planar ligand field of the N₂S₂ chromophore. The thiosemicarbazonato group is planar with Ni—S = 2.149 (1) Å and Ni—N(2) = 1.921 (2) Å. The coordination around Ni is trans planar with respect to the two S and two N atoms. The furan ring plane is at an angle of 3(1)° to the coordination plane. In the crystal of NOQCUS, the coordination environment around the nickel(II) ion is totally planar, as the NiN₂S₂ chromophore lies on its least-squares calculated plane and the four angles formed by the metal centre with the four donor atoms add up to exactly 360°. The Ni—N and Ni—S distances are within the usual range. This plane forms a 18° angle with the uncoordinated furan ring, which is also highly planar.

5. Synthesis and crystallization

17 mg (0.1 mmol) of (E)-2-(furan-2-ylmethylene)hydrazine-1-carbothioamide were dissolved in 30 mL of methanol then 13 mg (0.05 mmol) of Ni(OOCCH₃)₂·4H₂O were added. The reaction mixture was kept in air at room temperature for slow evaporation. After ca 2–3 d, orange crystals, suitable for X-ray analysis, were formed.

Yield 81%, soluble in DMSO, ethanol and dimethylformamide and insoluble in non-polar solvents. Elemental analysis: C₁₄H₂₀N₆NiO₄S₂ (M = 459.17); C 36.61 (calc. 36.62); H 4.35 (4.39); N 18.26 (18.30) %. IR (KBr): 3372 ν(OH), 2965 and 2854 ν(NH), 1643 ν(C=N) cm⁻¹.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. C-bound H atoms were positioned geometrically (C—H = 0.93 and 0.96 Å) and refined using a riding model with U_iso(H) = 1.2 or 1.5U_eq(C). O- and N-bound H atoms were located in difference Fourier maps [O2—H2O = 0.90 Å, N3—H3A = 0.90 Å, N3—H3B = 0.90 Å] and refined with U_iso(H) = 1.2U_eq(N) and 1.5U_eq(O), with their positions fixed. Two reflections (001) and (010), affected by the beam stop, were omitted in the final cycles of refinement.

Table 3
Experimental details

Crystal data
Chemical formula	[Ni(C₆H₆N₃OS)₂]·2CH₄O
M_r	459.19
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	6.5394 (11), 8.9611 (15), 10.2020 (15)
α, β, γ (°)	67.965 (5), 79.666 (6), 70.349 (6)
V (Å³)	520.92 (15)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	1.16
Crystal size (mm)	0.26 × 0.21 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.735, 0.861
No. of measured, independent and observed [I > 2σ(I)] reflections	8497, 2134, 1633
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.088, 1.04
No. of reflections	2134
No. of parameters	125
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.21
Computer programs: APEX4 (Bruker, 2008), SAINT (Bruker, 2008), SHELXT2016/6 (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b , ORTEP-3 for Windows (Farrugia, 2012 ), PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2269284

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989023005182/jy2031sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023005182/jy2031Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX4 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT2016/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

Bis{(Z)-N'-[(E)-(furan-2-yl)methylidene]carbamohydrazonothioato}nickel(II) methanol disolvate top

Crystal data top

[Ni(C₆H₆N₃OS)₂]·2CH₄O	Z = 1
M_r = 459.19	F(000) = 238
Triclinic, P1	D_x = 1.464 Mg m⁻³
a = 6.5394 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9611 (15) Å	Cell parameters from 2724 reflections
c = 10.2020 (15) Å	θ = 2.7–26.4°
α = 67.965 (5)°	µ = 1.16 mm⁻¹
β = 79.666 (6)°	T = 296 K
γ = 70.349 (6)°	Prism, orange
V = 520.92 (15) Å³	0.26 × 0.21 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	1633 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.046
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 26.4°, θ_min = 3.3°
T_min = 0.735, T_max = 0.861	h = −8→8
8497 measured reflections	k = −11→11
2134 independent reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0459P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2134 reflections	Δρ_max = 0.25 e Å⁻³
125 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

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
Ni1	0.500000	0.000000	0.500000	0.03949 (16)
S1	0.21552 (9)	0.08780 (8)	0.37725 (6)	0.0544 (2)
O1	0.8206 (3)	0.4874 (2)	0.41926 (18)	0.0592 (5)
O2	0.7620 (3)	0.3261 (2)	0.05737 (16)	0.0534 (4)
H2O	0.634939	0.350050	0.108389	0.080*
N1	0.5375 (3)	0.2167 (2)	0.39689 (17)	0.0403 (4)
N2	0.4320 (3)	0.3178 (2)	0.27263 (18)	0.0428 (4)
N3	0.1595 (3)	0.3562 (2)	0.1429 (2)	0.0558 (6)
H3A	0.195718	0.448305	0.083360	0.067*
H3B	0.032648	0.349515	0.126510	0.067*
C1	0.6747 (4)	0.4539 (3)	0.3592 (2)	0.0446 (5)
C2	0.8207 (5)	0.6480 (3)	0.3424 (3)	0.0688 (8)
H2	0.905332	0.703098	0.359617	0.083*
C3	0.6847 (5)	0.7162 (3)	0.2396 (3)	0.0679 (8)
H3	0.658018	0.824589	0.173586	0.082*
C4	0.5872 (4)	0.5926 (3)	0.2494 (3)	0.0544 (6)
H4	0.483563	0.604491	0.191646	0.065*
C5	0.6538 (3)	0.2881 (3)	0.4311 (2)	0.0440 (5)
H5	0.732223	0.223902	0.511529	0.053*
C6	0.2750 (3)	0.2665 (3)	0.2568 (2)	0.0415 (5)
C7	0.8122 (6)	0.1616 (4)	0.0563 (3)	0.0883 (10)
H7A	0.683980	0.143664	0.039468	0.132*
H7B	0.864640	0.082516	0.146089	0.132*
H7C	0.922412	0.146101	−0.017494	0.132*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0337 (2)	0.0371 (3)	0.0388 (2)	−0.01571 (17)	−0.00740 (15)	0.00392 (17)
S1	0.0428 (3)	0.0477 (4)	0.0586 (4)	−0.0248 (3)	−0.0200 (3)	0.0150 (3)
O1	0.0688 (12)	0.0533 (11)	0.0615 (11)	−0.0308 (9)	−0.0191 (8)	−0.0081 (8)
O2	0.0559 (10)	0.0439 (10)	0.0575 (10)	−0.0225 (8)	0.0064 (8)	−0.0116 (7)
N1	0.0346 (9)	0.0423 (10)	0.0352 (9)	−0.0157 (8)	−0.0070 (7)	0.0024 (8)
N2	0.0419 (10)	0.0435 (11)	0.0368 (10)	−0.0213 (8)	−0.0095 (8)	0.0040 (8)
N3	0.0505 (12)	0.0567 (13)	0.0511 (11)	−0.0293 (10)	−0.0223 (9)	0.0121 (10)
C1	0.0482 (13)	0.0444 (13)	0.0435 (12)	−0.0202 (10)	−0.0031 (10)	−0.0114 (11)
C2	0.087 (2)	0.0537 (17)	0.078 (2)	−0.0385 (15)	−0.0121 (16)	−0.0171 (15)
C3	0.095 (2)	0.0426 (15)	0.0671 (18)	−0.0308 (15)	−0.0135 (16)	−0.0068 (13)
C4	0.0675 (16)	0.0402 (14)	0.0540 (15)	−0.0191 (12)	−0.0152 (12)	−0.0063 (12)
C5	0.0457 (12)	0.0435 (13)	0.0366 (12)	−0.0171 (10)	−0.0090 (9)	−0.0005 (10)
C6	0.0350 (11)	0.0408 (12)	0.0391 (12)	−0.0152 (9)	−0.0050 (9)	0.0017 (10)
C7	0.101 (3)	0.0552 (19)	0.111 (3)	−0.0192 (17)	−0.003 (2)	−0.0358 (19)

Geometric parameters (Å, º) top

Ni1—N1	1.9055 (17)	N3—H3A	0.8997
Ni1—N1ⁱ	1.9055 (17)	N3—H3B	0.9000
Ni1—S1	2.1818 (6)	C1—C4	1.354 (3)
Ni1—S1ⁱ	2.1818 (6)	C1—C5	1.431 (3)
S1—C6	1.731 (2)	C2—C3	1.323 (4)
O1—C2	1.357 (3)	C2—H2	0.9300
O1—C1	1.384 (3)	C3—C4	1.419 (3)
O2—C7	1.402 (3)	C3—H3	0.9300
O2—H2O	0.9032	C4—H4	0.9300
N1—C5	1.305 (3)	C5—H5	0.9300
N1—N2	1.391 (2)	C7—H7A	0.9600
N2—C6	1.313 (3)	C7—H7B	0.9600
N3—C6	1.332 (3)	C7—H7C	0.9600

N1—Ni1—N1ⁱ	180.0	C3—C2—H2	124.4
N1—Ni1—S1	85.69 (5)	O1—C2—H2	124.4
N1ⁱ—Ni1—S1	94.31 (5)	C2—C3—C4	107.0 (2)
N1—Ni1—S1ⁱ	94.31 (5)	C2—C3—H3	126.5
N1ⁱ—Ni1—S1ⁱ	85.69 (5)	C4—C3—H3	126.5
S1—Ni1—S1ⁱ	180.0	C1—C4—C3	106.5 (2)
C6—S1—Ni1	95.83 (7)	C1—C4—H4	126.7
C2—O1—C1	106.13 (18)	C3—C4—H4	126.7
C7—O2—H2O	109.2	N1—C5—C1	127.45 (19)
C5—N1—N2	112.86 (16)	N1—C5—H5	116.3
C5—N1—Ni1	126.69 (14)	C1—C5—H5	116.3
N2—N1—Ni1	120.44 (13)	N2—C6—N3	117.99 (17)
C6—N2—N1	112.74 (15)	N2—C6—S1	122.47 (15)
C6—N3—H3A	116.5	N3—C6—S1	119.54 (16)
C6—N3—H3B	127.8	O2—C7—H7A	109.5
H3A—N3—H3B	114.4	O2—C7—H7B	109.5
C4—C1—O1	109.12 (19)	H7A—C7—H7B	109.5
C4—C1—C5	138.1 (2)	O2—C7—H7C	109.5
O1—C1—C5	112.71 (19)	H7A—C7—H7C	109.5
C3—C2—O1	111.2 (2)	H7B—C7—H7C	109.5

C5—N1—N2—C6	−163.93 (19)	N2—N1—C5—C1	2.4 (3)
Ni1—N1—N2—C6	15.0 (2)	Ni1—N1—C5—C1	−176.40 (17)
C2—O1—C1—C4	−0.7 (3)	C4—C1—C5—N1	5.6 (5)
C2—O1—C1—C5	−179.0 (2)	O1—C1—C5—N1	−176.8 (2)
C1—O1—C2—C3	0.3 (3)	N1—N2—C6—N3	178.56 (19)
O1—C2—C3—C4	0.2 (3)	N1—N2—C6—S1	−1.8 (3)
O1—C1—C4—C3	0.8 (3)	Ni1—S1—C6—N2	−8.9 (2)
C5—C1—C4—C3	178.5 (3)	Ni1—S1—C6—N3	170.73 (18)
C2—C3—C4—C1	−0.6 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N2	0.90	1.94	2.788 (3)	156
N3—H3A···O2ⁱⁱ	0.90	2.07	2.964 (3)	173
N3—H3B···O2ⁱⁱⁱ	0.90	2.12	3.009 (3)	171
C4—H4···N2	0.93	2.51	2.882 (3)	104
C5—H5···S1ⁱ	0.93	2.51	3.102 (3)	121

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

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

Contact	Distance	Symmetry operation
S1···C5	3.55	-1 + x, y, z
H2···O1	2.78	2 - x, 1 - y, 1 - z
N2···H2O	1.94	x, y, z
H3B···O2	2.12	-1 + x, y, z
H3A···O2	2.07	1 - x, 1 - y, 1 - z
C1···C1	3.51	1 - x, 1 - y, 1 - z
H3B···H3A	2.55	-x, 1 - y, -z
H7C···H7C	2.38	2 - x, -y, -z

Acknowledgements

The author's contributions are as follows. Conceptualization, MA and AB; synthesis, ANA and GZM; X-ray analysis, ANA, GZM, STÇ and MA; writing (review and editing of the manuscript) STÇ, MA and AB; funding acquisition, ANA and GZM; supervision, MA and AB.

Funding information

This work was supported partially by Azerbaijan Medical University and Baku State University.

References

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