Crystal structure of tetra­kis­(μ-4-benzyl-4H-1,2,4-triazole-κ2N1:N2)tetra­fluoridodi-μ2-oxido-dioxidodisilver(I)divanadium(V)

Senchyk, G.A.; Lysenko, A.B.; Rusanov, E.B.; Domasevitch, K.V.

doi:10.1107/S2056989022001712

research communications

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ISSN: 2056-9890

Volume 78| Part 4| April 2022| Pages 399-403

https://doi.org/10.1107/S2056989022001712

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Crystal structure of tetrakis(μ-4-benzyl-4H-1,2,4-triazole-κ²N¹:N²)tetrafluoridodi-μ₂-oxido-dioxidodisilver(I)divanadium(V)

Ganna A. Senchyk,^a ^* Andrey B. Lysenko,^a Eduard B. Rusanov ^b and Kostiantyn V. Domasevitch ^a

^aInorganic Chemistry Department, Taras Shevchenko National University of Kyiv, Volodymyrska Street, 64, Kyiv 01033, Ukraine, and ^bInstitute of Organic Chemistry, Murmanska Street, 5, Kyiv, 02660, Ukraine
^*Correspondence e-mail: senchyk.ganna@gmail.com

Edited by G. Diaz de Delgado, Universidad de Los Andes, Venezuela (Received 14 October 2021; accepted 14 February 2022; online 15 March 2022)

The crystal structure of the title compound, [Ag₂(VO₂F₂)₂(C₉H₉N₃)₄], is presented. The molecular complex is based on the heterobimetallic Ag^I—V^V fragment {Ag^I₂(V^VO₂F₂)₂(tr)₄} supported by four 1,2,4-triazole ligands [4-benzyl-(4H-1,2,4-triazol-4-yl)]. The triazole functional group demonstrates homo- and heterometallic connectivity (Ag—Ag and Ag—V) of the metal centers through the [–NN–] double and single bridges, respectively. The vanadium atom possesses a distorted trigonal–bipyramidal coordination environment [VO₂F₂N] with the Reedijk structural parameter τ = 0.59. In the crystal, C—H⋯O and C—H⋯F hydrogen bonds as well as C—H⋯π contacts are observed involving the organic ligands and the vanadium oxofluoride anions. A Hirshfeld surface analysis of the hydrogen-bonding interactions is also described.

Keywords: silver(I); vanadium(V) oxofluoride; 1,2,4-triazole; Hirshfeld surface analysis; crystal structure.

CCDC reference: 2151864

1. Chemical context

There is considerable interest in the chemistry of organic–inorganic hybrids, including the vanadium oxide–fluoride (VOF) matrix, which is motivated by the numerous potential applications in catalysis, magnetism, optics, etc. (Dolbecq et al., 2010 ; Monakhov et al., 2015 ). Incorporation of silver(I) in VOF solid can afford materials such as Ag₄V₂O₆F₂ (Sorensen et al., 2005 ; Albrecht et al., 2009 ) and Ag₃VO₂F₄ (Chamberlain et al., 2010 ), which are attractive candidates for solid-state battery technologies. The formation of Ag^I–VOF heterobimetallic secondary building units (SBUs) in coordination compounds remains a non-trivial challenge. The 1,2,4-triazole heterocycle, as a functional group, demonstrates a favorable coordination affinity towards Ag^I cations, connecting them into polynuclear units (Aromí et al., 2011 ). At the same time, it possesses a hidden capability to bind two different metal ions through a short –NN– bridge, usually Cu^II–tr–Mo^VI (Tian et al., 2011 ; Lysenko et al., 2016 ; Senchyk et al., 2017 ; Zhu et al., 2012 ) but there are some other rare examples including Cu^I–tr–V^IV (Sharga et al., 2010 ) and Ag^I–tr–Mo^VI (Tian et al., 2017 ). This may be realized in the case of constructing SBUs with a terminal N¹-triazole function that has an open site accessible to coordination. We demonstrated this principle in the self-association of Ag^I–VOF heterobimetallic coordination compounds based on {Ag^I₂(V^VO₂F₂)₂(tr)₄} SBUs with bi-1,2,4-triazole ligands with different geometries (Senchyk et al., 2012 ). Such units seem to be very favorable and stable, and form even in the presence of a heterobifunctional 1,2,4-triazole-carboxylate ligand (Senchyk et al., 2019 ). In the present contribution we extend the library of Ag^I–VOF compounds, adding the title complex [Ag₂(VO₂F₂)₂(tr-CH₂Ph)₄] (I), which has the ligand 4-benzyl-(4H-1,2,4-triazol-4-yl) (tr-CH₂Ph).

2. Structural commentary

Compound I crystallizes in the monoclinic space group P2₁/c. Its asymmetric unit contains one Ag^I cation, one [V^VO₂F₂]⁻ anion and two organic ligands (tr-CH₂Ph), which, after inversion across a center of symmetry, form the molecular tetranuclear cluster {Ag^I₂(V^VO₂F₂)₂(tr-CH₂Ph)₄} (Fig. 1). Two 1,2,4-triazole ligands bridge two adjacent silver atoms [the Ag⋯Agⁱ distance is 4.2497 (5) Å; symmetry code (i) −x, −y + 1, −z], while the other two link Ag and V centers [the Ag⋯V distance is 3.8044 (6) Å]. Thus, the coordination environment of the Ag^I cation can be described as [AgN₃O] with typical Ag—N(triazole) bond lengths [in the range of 2.197 (2) – 2.390 (3) Å] and a slightly elongated Ag—O bond [2.562 (2) Å] (Table 1). The V^V atom possesses a distorted trigonal–bipyramidal coordination environment [VO₂F₂N] with V—F [1.828 (2) and 1.8330 (18) Å], two short V—O [1.632 (2) and 1.660 (2) Å] and elongated V—N [2.203 (2) Å] bonds (Table 1). The geometry of the vanadium oxofluoride polyhedra is characterized by the Reedijk structural parameter τ (Addison et al., 1984 ) of 0.59 (for a square-pyramidal geometry, τ = 0 and for trigonal–bipyramidal, τ = 1). A bond-valence-sum calculation for the {VO₂F₂N} polyhedra confirms the +5 oxidation state for the vanadium atom.

Table 1
Selected geometric parameters (Å, °)

Ag1—N5ⁱ	2.197 (2)	V1—O2	1.660 (2)
Ag1—N1	2.233 (2)	V1—F1	1.828 (2)
Ag1—N4	2.390 (3)	V1—F2	1.8330 (18)
Ag1—O1	2.562 (2)	V1—N2	2.203 (2)
V1—O1	1.632 (2)

N5ⁱ—Ag1—N1	140.62 (9)	O1—V1—F2	117.63 (10)
N5ⁱ—Ag1—N4	102.45 (9)	O2—V1—F2	132.25 (10)
N1—Ag1—N4	112.90 (9)	F1—V1—F2	86.76 (10)
N5ⁱ—Ag1—O1	129.87 (8)	O1—V1—N2	87.14 (10)
N1—Ag1—O1	75.28 (8)	O2—V1—N2	88.78 (11)
N4—Ag1—O1	79.39 (8)	F1—V1—N2	167.32 (10)
O1—V1—O2	108.04 (11)	F2—V1—N2	80.59 (9)
O1—V1—F1	99.57 (11)	V1—O1—Ag1	128.89 (11)
O2—V1—F1	99.21 (13)
Symmetry code: (i) .

Figure 1
The molecular structure of compound I, showing the atom-labeling scheme [symmetry code: (i) −x, −y + 1, −z]. Displacement ellipsoids are drawn at the 30% probability level.

3. Supramolecular features

Since the organic ligand contains a hydrophobic benzyl tail, the crystal structure of I involves no solvate water molecules. Thus, the only hydrogen bonds observed are of the type C—H⋯O, C—H⋯F and C—H⋯π contacts (Figs. 2 and 3, Table 2). The central 1,2,4-triazole unit, which bridges two Ag ions, displays intramolecular C10—H10⋯O2 [3.082 (4) Å] and intermolecular C11—H11⋯F1^v [2.935 (4) Å, symmetry code (v) −x + 1, −y + 1, −z] hydrogen-bond contacts. The other triazole group, which provides the heterometallic Ag–V linkage, forms bifurcated C—H⋯O and C—H⋯F contacts with vanadium oxofluoride anions of neighboring molecular complexes. Additionally, methylene –CH₂– fragments show directed C—H⋯O and C—H⋯F contacts to the VOF fragments. The phenyl rings are here oriented towards each other in an edge-to-face C—H⋯π interaction mode.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2ⁱⁱ	0.93	2.44	3.289 (4)	153
C1—H1⋯F2ⁱⁱⁱ	0.93	2.63	3.108 (4)	113
C2—H2⋯F1^iv	0.93	2.07	2.935 (4)	154
C2—H2⋯F2^iv	0.93	2.60	3.304 (4)	133
C3—H3A⋯O1ⁱⁱⁱ	0.97	2.73	3.465 (4)	133
C3—H3B⋯F2ⁱⁱⁱ	0.97	2.37	3.006 (4)	123
C10—H10⋯O2	0.93	2.16	3.082 (4)	170
C11—H11⋯F1^v	0.93	2.07	2.935 (4)	153
C12—H12A⋯O1^v	0.97	2.65	3.388 (2)	133
C16—H16⋯O2^vi	0.93	2.42	3.339 (9)	172
C18—H18⋯O1^v	0.93	2.83	3.589 (15)	139
Symmetry codes: (ii) ; (iii) ; (iv) ; (v) ; (vi) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
Projection on the bc plane showing the crystal packing of compound I. Vanadium oxofluoride anions are shown as polyhedra. [Atoms are colored as follows: silver – cyan, vanadium – dark green, oxygen – red, fluorine – green, nitrogen – blue, carbon – gray, hydrogen – white.]

Figure 3
Hydrogen-bonding arrangement in the structure of I showing C—H⋯O and C—H⋯F contacts [symmetry codes: (ii) x − 1, y, z; (iii) −x, −y + 1, −z + 1; (iv) −x + 1, −y + 1, −z + 1; (v) −x + 1, −y + 1, −z; (vi) x, −y + $[{3\over 2}]$ , z − $[{1\over 2}]$ .]. Phenyl groups are omitted for clarity.

Supramolecular interactions in the title structure were studied through Hirshfeld surface analysis (Spackman & Byrom, 1997 ; McKinnon et al., 2004 ; Hirshfeld, 1977 ; Spackman & McKinnon, 2002 ), performed with CrystalExplorer17 (Turner et al., 2017 ), taking into account only the major contribution of the disordered group. The Hirshfeld surface, mapped over d_norm using a fixed color scale of −0.488 (red) to 1.385 (blue) a.u. visualizes the set of shortest intermolecular contacts (Fig. 4). All of them correspond to the hydrogen-bond interactions, which fall into three categories. The strongest hydrogen bonds to F-atom acceptors are reflected by the most prominent red spots (−0.469 to −0.488 a.u.), whereas a group of medium intensity spots (−0.182 to −0.261 a.u.) identify weaker C—H⋯O bonds with the terminal oxide O2. However, even more distal interactions with the bridging oxide O1 are still distinguishable on the surface, in the form of very diffuse, less intense spots (−0.066 to −0.142 a.u.).

Figure 4
The Hirshfeld surface of the title compound mapped over d_norm in the color range −0.488 (red) to 1.385 (blue) a.u., in the environment of the closest neighbor [symmetry code: −x + 1, −y + 1, −z], with the red spots indicating different kinds of intermolecular interactions.

The contribution of different kinds of interatomic contacts to the Hirshfeld surface is shown in the fingerprint plots in Fig. 5. A significant fraction of the E⋯H/H⋯E (E = C, N, O, F) contacts (in total 60.1%) suggests the dominant role of the hydrogen-bond interactions. The strongest ones (E = O, F) have a similar nature and they are reflected by pairs of spikes pointing to the lower left of the plot. However, the contribution from the contacts with F-atom acceptors is higher (15.6% for F⋯H/H⋯F and 11.6% for O⋯H/H⋯O) and they are also essentially shorter, as indicated by different lengths of the spikes (the shortest contacts are F⋯H = 2.0 and O⋯H = 2.2 Å). One may suppose that the preferable sites for hydrogen bonding of the vanadium oxofluoride groups are the F atoms. This is consistent with the results of Hirshfeld analysis for the [VOF₅]²⁻ anion 4,4′-(propane-1,3-diyl)bis(4H-1,2,4-triazol-1-ium) salt (Senchyk et al., 2020 ).

Figure 5
Two-dimensional fingerprint plots for the title compound, and those delineated into the principal contributions of H⋯H, C⋯H/H⋯C, F⋯H/H⋯F, O⋯H/H⋯O, N⋯H/H⋯N, C⋯C, C⋯N/N⋯C and Ag⋯H/H⋯Ag contacts. Other observed contacts are N⋯N (0.4%), C⋯F/F⋯C (0.1%) and C⋯O/O⋯C (0.1%).

The plots indicate close resemblance of the N⋯H/H⋯N (10.7%) and C⋯H/H⋯C (22.2%) contacts, which appear as pairs of nearly identical, very diffuse and short features (N⋯H = 2.9 and C⋯H = 2.9 Å). Both of them correspond to edge-to-face stacking or C—H⋯π interactions involving either the phenyl or triazole rings. The contribution from mutual π–π interactions of the latter delivers minor fractions of the C⋯C, N⋯N and C⋯N/N⋯C contacts, which account in total for only 2.6%. The shortest contact of this series [C⋯N = 3.5 Å] exceeds the sum of the van der Waals radii [3.25 Å] and π–π interactions are not associated with red spots of the d_norm surface. A comparable contribution is due to the distal anagostic contacts Ag⋯H/H⋯Ag (2.9%) with the polarized methylene H atoms. There are no mutual π–π interactions involving phenyl rings, which are responsible for larger fractions of the C⋯C contacts in the case of polycyclic species (Spackman & McKinnon, 2002).

4. Database survey

A structure survey was carried out in the Cambridge Structural Database (CSD version 5.43, update of November 2021; Groom et al., 2016 ) for 4-benzyl-(4H-1,2,4-triazol-4-yl) and it revealed five hits for coordination compounds based on this ligand. There are no examples of Ag^I compounds, only two Fe^II complexes [FAYQAA (Pittala et al., 2017a ) and XASVEV (Pittala et al., 2017b )] and three Cu^II–POM complexes [YUGLIX and YUGLOD (Tian et al., 2015 ) and ZUXLAI (Zhang et al., 2020 )]. Moreover, there are no examples of heterometallic connection through an –NN– triazole bridge for the 4-benzyl-(4H-1,2,4-triazol-4-yl) ligand.

5. Synthesis and crystallization

4-Benzyl-(4H-1,2,4-triazol-4-yl) (tr-CH₂Ph) was synthesized by refluxing benzylamine (5.35 g, 50.0 mmol) and dimethylformamide azine (17.75 g, 125.0 mmol) in the presence of toluenesulfonic acid monohydrate (0.86 g, 5.0 mmol) as a catalyst in DMF (30.0 ml).

Compound I was prepared under hydrothermal conditions. A mixture of AgOAc (16.7 mg, 0.100 mmol), tr-CH₂Ph (20.7 mg, 0.130 mmol), V₂O₅ (9.1 mg, 0.050 mmol) and 5 mL of water with aqueous HF (50%, 150 µL, 4.33 mmol) was added into a Teflon vessel. Then the components were heated at 423 K for 24 h and slowly cooled to room temperature over 50 h, yielding light-yellow prisms of I (yield 33.4 mg, 61%).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. For one of the organic ligands, the benzyl linkage (C12–C18) is unequally disordered over two overlapping positions with refined partial contribution factors of 0.68 (3) and 0.32 (3). The major part of the disorder was freely refined anisotropically, while atoms of the minor contributor were refined anisotropically with a restrained geometry for the phenyl ring, rigid-bond restraints applied to the –CH₂C₆H₅ linkage and similarity restraints applied to the closely separated contributions of C12 and C12A, C13 and C13A. H atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å (CH) and 0.97 Å (CH₂) and with U_iso(H) = 1.2U_eq(C).

Table 3
Experimental details

Crystal data
Chemical formula	[Ag₂V₂F₄O₄(C₉H₉N₃)₄]
M_r	1094.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.5484 (2), 21.2439 (6), 12.5910 (4)
β (°)	90.910 (2)
V (Å³)	2018.81 (10)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.48
Crystal size (mm)	0.27 × 0.14 × 0.12

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.657, 0.856
No. of measured, independent and observed [I > 2σ(I)] reflections	22923, 5125, 3468
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.078, 1.02
No. of reflections	5125
No. of parameters	323
No. of restraints	65
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.42
Computer programs: APEX2 and SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008 ), SHELXL2014/7 (Sheldrick, 2015 ), DIAMOND (Brandenburg, 1999 ) and WinGX (Farrugia, 2012 ).

Supporting information

CCDC reference: 2151864

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989022001712/dj2039sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022001712/dj2039Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012).

Tetrakis(µ-4-benzyl-4H-1,2,4-triazole-κ²N¹:N²)tetrafluoridodi-µ₂-oxido-dioxidodisilver(I)divanadium(V) top

Crystal data top

[Ag₂V₂F₄O₄(C₉H₉N₃)₄]	F(000) = 1088
M_r = 1094.39	D_x = 1.800 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.5484 (2) Å	Cell parameters from 4931 reflections
b = 21.2439 (6) Å	θ = 2.5–23.8°
c = 12.5910 (4) Å	µ = 1.48 mm⁻¹
β = 90.910 (2)°	T = 296 K
V = 2018.81 (10) Å³	Block, colorless
Z = 2	0.27 × 0.14 × 0.12 mm

Data collection top

Bruker APEXII area-detector diffractometer	3468 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
ω scans	θ_max = 28.7°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
T_min = 0.657, T_max = 0.856	k = −26→28
22923 measured reflections	l = −16→14
5125 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0194P)² + 2.1764P] where P = (F_o² + 2F_c²)/3
5125 reflections	(Δ/σ)_max = 0.001
323 parameters	Δρ_max = 0.58 e Å⁻³
65 restraints	Δρ_min = −0.42 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.00892 (3)	0.49751 (2)	0.16871 (2)	0.04174 (9)
V1	0.43103 (7)	0.48341 (2)	0.33615 (4)	0.03165 (13)
F1	0.6173 (3)	0.42871 (13)	0.32820 (16)	0.0802 (8)
F2	0.3957 (2)	0.45217 (9)	0.46985 (15)	0.0471 (5)
O1	0.3065 (3)	0.45593 (10)	0.23966 (17)	0.0407 (5)
O2	0.5296 (3)	0.54823 (11)	0.29314 (16)	0.0424 (6)
N1	0.0417 (3)	0.54163 (12)	0.32878 (19)	0.0315 (6)
N2	0.2025 (3)	0.54132 (11)	0.38181 (19)	0.0301 (6)
N3	0.0147 (3)	0.59315 (11)	0.47783 (18)	0.0292 (6)
N4	0.2055 (4)	0.54025 (13)	0.0405 (2)	0.0386 (6)
N5	0.1929 (3)	0.54905 (12)	−0.06853 (19)	0.0345 (6)
N6	0.4464 (3)	0.58619 (12)	−0.0125 (2)	0.0342 (6)
C1	−0.0684 (4)	0.57241 (14)	0.3893 (2)	0.0337 (7)
H1	−0.1876	0.5790	0.3732	0.040*
C2	0.1821 (4)	0.57219 (14)	0.4702 (2)	0.0328 (7)
H2	0.2710	0.5788	0.5209	0.039*
C3	−0.0650 (4)	0.62351 (15)	0.5708 (2)	0.0400 (8)
H3A	−0.0579	0.5945	0.6301	0.048*
H3B	−0.1896	0.6308	0.5552	0.048*
C4	0.0174 (4)	0.68457 (14)	0.6044 (2)	0.0308 (7)
C5	0.0024 (5)	0.73774 (17)	0.5430 (3)	0.0490 (9)
H5	−0.0493	0.7354	0.4756	0.059*
C6	0.0646 (6)	0.79525 (19)	0.5816 (4)	0.0696 (13)
H6	0.0537	0.8314	0.5403	0.084*
C7	0.1417 (6)	0.7982 (2)	0.6806 (5)	0.0775 (15)
H7	0.1817	0.8367	0.7068	0.093*
C8	0.1607 (6)	0.7456 (3)	0.7410 (4)	0.0752 (14)
H8	0.2152	0.7479	0.8076	0.090*
C9	0.0986 (5)	0.68877 (19)	0.7030 (3)	0.0517 (10)
H9	0.1118	0.6528	0.7444	0.062*
C10	0.3594 (4)	0.56283 (15)	0.0704 (2)	0.0385 (8)
H10	0.4025	0.5627	0.1400	0.046*
C11	0.3391 (4)	0.57667 (15)	−0.0972 (2)	0.0369 (7)
H11	0.3652	0.5881	−0.1665	0.044*
C12	0.6224 (7)	0.6171 (4)	−0.0050 (16)	0.040 (3)	0.68 (3)
H12A	0.7076	0.5936	−0.0462	0.048*	0.68 (3)
H12B	0.6633	0.6178	0.0684	0.048*	0.68 (3)
C13	0.608 (2)	0.6830 (4)	−0.0465 (10)	0.0356 (18)	0.68 (3)
C14	0.5342 (18)	0.7259 (6)	0.0216 (12)	0.049 (2)	0.68 (3)
H14	0.4990	0.7131	0.0887	0.058*	0.68 (3)
C15	0.5119 (14)	0.7881 (5)	−0.009 (2)	0.068 (4)	0.68 (3)
H15	0.4623	0.8171	0.0370	0.081*	0.68 (3)
C16	0.5640 (18)	0.8063 (5)	−0.1083 (18)	0.065 (5)	0.68 (3)
H16	0.5470	0.8478	−0.1295	0.078*	0.68 (3)
C17	0.639 (2)	0.7654 (8)	−0.1755 (12)	0.072 (4)	0.68 (3)
H17	0.6767	0.7787	−0.2417	0.086*	0.68 (3)
C18	0.660 (2)	0.7029 (7)	−0.1450 (11)	0.057 (3)	0.68 (3)
H18	0.7102	0.6743	−0.1917	0.069*	0.68 (3)
C12A	0.6197 (12)	0.6178 (8)	−0.026 (3)	0.034 (4)	0.32 (3)
H12C	0.6862	0.5951	−0.0794	0.041*	0.32 (3)
H12D	0.6862	0.6157	0.0400	0.041*	0.32 (3)
C13A	0.605 (4)	0.6853 (8)	−0.060 (2)	0.035 (4)	0.32 (3)
C14A	0.530 (3)	0.7370 (10)	−0.0096 (18)	0.038 (4)	0.32 (3)
H14A	0.4803	0.7324	0.0570	0.046*	0.32 (3)
C15A	0.530 (2)	0.7955 (8)	−0.059 (2)	0.048 (5)	0.32 (3)
H15A	0.4797	0.8300	−0.0254	0.057*	0.32 (3)
C16A	0.604 (2)	0.8023 (6)	−0.1587 (19)	0.047 (4)	0.32 (3)
H16A	0.6038	0.8415	−0.1917	0.056*	0.32 (3)
C17A	0.679 (3)	0.7507 (8)	−0.2089 (17)	0.044 (4)	0.32 (3)
H17A	0.7284	0.7553	−0.2755	0.053*	0.32 (3)
C18A	0.679 (4)	0.6922 (7)	−0.159 (2)	0.039 (5)	0.32 (3)
H18A	0.7289	0.6576	−0.1931	0.046*	0.32 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.04650 (15)	0.04865 (17)	0.02972 (13)	−0.00637 (12)	−0.01010 (10)	−0.00375 (12)
V1	0.0375 (3)	0.0324 (3)	0.0249 (3)	0.0025 (2)	−0.0031 (2)	0.0009 (2)
F1	0.0848 (17)	0.121 (2)	0.0337 (12)	0.0688 (16)	−0.0171 (12)	−0.0150 (13)
F2	0.0453 (11)	0.0559 (13)	0.0398 (11)	−0.0063 (9)	−0.0038 (9)	0.0181 (9)
O1	0.0490 (14)	0.0397 (13)	0.0330 (12)	0.0045 (10)	−0.0085 (11)	−0.0072 (10)
O2	0.0326 (12)	0.0692 (16)	0.0253 (11)	−0.0118 (11)	−0.0045 (10)	0.0048 (11)
N1	0.0264 (13)	0.0414 (16)	0.0264 (13)	−0.0014 (11)	−0.0060 (11)	−0.0052 (11)
N2	0.0282 (13)	0.0329 (14)	0.0290 (14)	0.0001 (11)	−0.0083 (11)	−0.0044 (11)
N3	0.0341 (14)	0.0300 (14)	0.0235 (14)	−0.0013 (11)	−0.0001 (11)	−0.0039 (10)
N4	0.0502 (17)	0.0411 (16)	0.0242 (14)	−0.0115 (13)	−0.0049 (12)	0.0053 (12)
N5	0.0402 (15)	0.0408 (16)	0.0223 (13)	−0.0068 (12)	−0.0028 (12)	−0.0022 (11)
N6	0.0363 (14)	0.0373 (15)	0.0287 (14)	−0.0043 (11)	−0.0056 (12)	0.0021 (11)
C1	0.0256 (16)	0.0412 (19)	0.0341 (17)	0.0004 (13)	−0.0084 (14)	−0.0044 (14)
C2	0.0309 (16)	0.0373 (18)	0.0300 (17)	0.0005 (13)	−0.0085 (14)	−0.0051 (14)
C3	0.047 (2)	0.0395 (19)	0.0337 (18)	−0.0056 (15)	0.0107 (16)	−0.0084 (15)
C4	0.0270 (16)	0.0316 (17)	0.0339 (17)	0.0017 (13)	0.0031 (13)	−0.0065 (13)
C5	0.046 (2)	0.046 (2)	0.055 (2)	−0.0040 (17)	−0.0043 (18)	0.0073 (18)
C6	0.062 (3)	0.037 (2)	0.110 (4)	−0.004 (2)	0.013 (3)	0.009 (2)
C7	0.070 (3)	0.062 (3)	0.101 (4)	−0.024 (2)	0.023 (3)	−0.043 (3)
C8	0.067 (3)	0.105 (4)	0.053 (3)	−0.028 (3)	0.001 (2)	−0.034 (3)
C9	0.054 (2)	0.062 (3)	0.039 (2)	−0.0041 (19)	−0.0045 (18)	−0.0032 (18)
C10	0.052 (2)	0.0395 (19)	0.0239 (16)	−0.0072 (16)	−0.0098 (15)	0.0055 (14)
C11	0.0428 (19)	0.046 (2)	0.0220 (16)	−0.0028 (16)	−0.0040 (14)	0.0020 (14)
C12	0.036 (3)	0.049 (3)	0.036 (8)	−0.008 (3)	−0.010 (3)	0.006 (3)
C13	0.031 (3)	0.036 (3)	0.040 (4)	−0.008 (3)	−0.008 (3)	−0.004 (3)
C14	0.046 (4)	0.049 (5)	0.052 (5)	0.001 (4)	−0.003 (4)	−0.003 (4)
C15	0.046 (4)	0.042 (5)	0.115 (12)	0.002 (3)	−0.008 (6)	−0.012 (6)
C16	0.052 (6)	0.050 (5)	0.093 (13)	−0.016 (4)	−0.022 (7)	0.033 (6)
C17	0.080 (9)	0.081 (9)	0.053 (7)	−0.027 (7)	−0.009 (5)	0.019 (6)
C18	0.066 (8)	0.054 (5)	0.052 (6)	−0.017 (5)	−0.005 (5)	−0.008 (5)
C12A	0.037 (6)	0.046 (5)	0.020 (9)	0.001 (5)	−0.009 (4)	0.003 (4)
C13A	0.035 (6)	0.032 (5)	0.037 (7)	−0.004 (5)	−0.005 (6)	−0.001 (5)
C14A	0.034 (7)	0.044 (8)	0.036 (9)	−0.004 (5)	0.001 (7)	0.004 (6)
C15A	0.061 (11)	0.035 (8)	0.048 (11)	0.005 (7)	0.004 (9)	−0.001 (7)
C16A	0.045 (9)	0.040 (7)	0.055 (10)	−0.010 (6)	0.002 (7)	0.005 (7)
C17A	0.047 (9)	0.036 (7)	0.050 (9)	−0.006 (5)	0.005 (6)	0.000 (6)
C18A	0.048 (10)	0.036 (7)	0.032 (8)	−0.010 (6)	0.004 (6)	0.002 (5)

Geometric parameters (Å, º) top

Ag1—N5ⁱ	2.197 (2)	C7—H7	0.9300
Ag1—N1	2.233 (2)	C8—C9	1.378 (6)
Ag1—N4	2.390 (3)	C8—H8	0.9300
Ag1—O1	2.562 (2)	C9—H9	0.9300
V1—O1	1.632 (2)	C10—H10	0.9300
V1—O2	1.660 (2)	C11—H11	0.9300
V1—F1	1.828 (2)	C12—C13	1.497 (5)
V1—F2	1.8330 (18)	C12—H12A	0.9700
V1—N2	2.203 (2)	C12—H12B	0.9700
N1—C1	1.311 (4)	C13—C18	1.374 (9)
N1—N2	1.376 (3)	C13—C14	1.375 (8)
N2—C2	1.303 (4)	C14—C15	1.386 (11)
N3—C1	1.345 (4)	C14—H14	0.9300
N3—C2	1.345 (4)	C15—C16	1.371 (12)
N3—C3	1.473 (4)	C15—H15	0.9300
N4—C10	1.306 (4)	C16—C17	1.344 (13)
N4—N5	1.387 (3)	C16—H16	0.9300
N5—C11	1.306 (4)	C17—C18	1.390 (11)
N5—Ag1ⁱ	2.197 (2)	C17—H17	0.9300
N6—C10	1.339 (4)	C18—H18	0.9300
N6—C11	1.344 (4)	C12A—C13A	1.497 (6)
N6—C12A	1.484 (5)	C12A—H12C	0.9700
N6—C12	1.484 (5)	C12A—H12D	0.9700
C1—H1	0.9300	C13A—C14A	1.3900
C2—H2	0.9300	C13A—C18A	1.3900
C3—C4	1.497 (4)	C14A—C15A	1.3900
C3—H3A	0.9700	C14A—H14A	0.9300
C3—H3B	0.9700	C15A—C16A	1.3900
C4—C5	1.372 (5)	C15A—H15A	0.9300
C4—C9	1.378 (4)	C16A—C17A	1.3900
C5—C6	1.393 (5)	C16A—H16A	0.9300
C5—H5	0.9300	C17A—C18A	1.3900
C6—C7	1.369 (6)	C17A—H17A	0.9300
C6—H6	0.9300	C18A—H18A	0.9300
C7—C8	1.358 (7)

N5ⁱ—Ag1—N1	140.62 (9)	C7—C8—C9	119.6 (4)
N5ⁱ—Ag1—N4	102.45 (9)	C7—C8—H8	120.2
N1—Ag1—N4	112.90 (9)	C9—C8—H8	120.2
N5ⁱ—Ag1—O1	129.87 (8)	C8—C9—C4	120.9 (4)
N1—Ag1—O1	75.28 (8)	C8—C9—H9	119.6
N4—Ag1—O1	79.39 (8)	C4—C9—H9	119.6
O1—V1—O2	108.04 (11)	N4—C10—N6	110.8 (3)
O1—V1—F1	99.57 (11)	N4—C10—H10	124.6
O2—V1—F1	99.21 (13)	N6—C10—H10	124.6
O1—V1—F2	117.63 (10)	N5—C11—N6	110.5 (3)
O2—V1—F2	132.25 (10)	N5—C11—H11	124.8
F1—V1—F2	86.76 (10)	N6—C11—H11	124.8
O1—V1—N2	87.14 (10)	N6—C12—C13	109.3 (8)
O2—V1—N2	88.78 (11)	N6—C12—H12A	109.8
F1—V1—N2	167.32 (10)	C13—C12—H12A	109.8
F2—V1—N2	80.59 (9)	N6—C12—H12B	109.8
V1—O1—Ag1	128.89 (11)	C13—C12—H12B	109.8
C1—N1—N2	106.4 (2)	H12A—C12—H12B	108.3
C1—N1—Ag1	132.19 (19)	C18—C13—C14	118.9 (7)
N2—N1—Ag1	121.35 (18)	C18—C13—C12	125.6 (13)
C2—N2—N1	107.3 (2)	C14—C13—C12	115.5 (13)
C2—N2—V1	127.4 (2)	C13—C14—C15	120.4 (8)
N1—N2—V1	124.36 (18)	C13—C14—H14	119.8
C1—N3—C2	105.0 (2)	C15—C14—H14	119.8
C1—N3—C3	127.7 (3)	C16—C15—C14	119.2 (9)
C2—N3—C3	126.7 (3)	C16—C15—H15	120.4
C10—N4—N5	106.5 (2)	C14—C15—H15	120.4
C10—N4—Ag1	120.2 (2)	C17—C16—C15	121.4 (8)
N5—N4—Ag1	133.30 (19)	C17—C16—H16	119.3
C11—N5—N4	106.8 (2)	C15—C16—H16	119.3
C11—N5—Ag1ⁱ	128.7 (2)	C16—C17—C18	119.4 (8)
N4—N5—Ag1ⁱ	122.94 (19)	C16—C17—H17	120.3
C10—N6—C11	105.4 (3)	C18—C17—H17	120.3
C10—N6—C12A	134.8 (15)	C13—C18—C17	120.7 (9)
C11—N6—C12A	119.7 (15)	C13—C18—H18	119.7
C10—N6—C12	124.3 (8)	C17—C18—H18	119.7
C11—N6—C12	130.2 (7)	N6—C12A—C13A	113.8 (16)
N1—C1—N3	110.7 (3)	N6—C12A—H12C	108.8
N1—C1—H1	124.6	C13A—C12A—H12C	108.8
N3—C1—H1	124.6	N6—C12A—H12D	108.8
N2—C2—N3	110.6 (3)	C13A—C12A—H12D	108.8
N2—C2—H2	124.7	H12C—C12A—H12D	107.7
N3—C2—H2	124.7	C14A—C13A—C18A	120.0
N3—C3—C4	115.5 (3)	C14A—C13A—C12A	131.1 (18)
N3—C3—H3A	108.4	C18A—C13A—C12A	108.9 (19)
C4—C3—H3A	108.4	C13A—C14A—C15A	120.0
N3—C3—H3B	108.4	C13A—C14A—H14A	120.0
C4—C3—H3B	108.4	C15A—C14A—H14A	120.0
H3A—C3—H3B	107.5	C16A—C15A—C14A	120.0
C5—C4—C9	119.0 (3)	C16A—C15A—H15A	120.0
C5—C4—C3	121.6 (3)	C14A—C15A—H15A	120.0
C9—C4—C3	119.2 (3)	C15A—C16A—C17A	120.0
C4—C5—C6	120.1 (4)	C15A—C16A—H16A	120.0
C4—C5—H5	120.0	C17A—C16A—H16A	120.0
C6—C5—H5	120.0	C18A—C17A—C16A	120.0
C7—C6—C5	119.6 (4)	C18A—C17A—H17A	120.0
C7—C6—H6	120.2	C16A—C17A—H17A	120.0
C5—C6—H6	120.2	C17A—C18A—C13A	120.0
C8—C7—C6	120.8 (4)	C17A—C18A—H18A	120.0
C8—C7—H7	119.6	C13A—C18A—H18A	120.0
C6—C7—H7	119.6

O2—V1—O1—Ag1	−74.41 (17)	Ag1—N4—C10—N6	−178.0 (2)
F1—V1—O1—Ag1	−177.46 (15)	C11—N6—C10—N4	−0.4 (4)
F2—V1—O1—Ag1	91.19 (15)	C12A—N6—C10—N4	178.8 (12)
N2—V1—O1—Ag1	13.37 (14)	C12—N6—C10—N4	178.0 (6)
C1—N1—N2—C2	−0.7 (3)	N4—N5—C11—N6	0.1 (4)
Ag1—N1—N2—C2	177.7 (2)	Ag1ⁱ—N5—C11—N6	−165.5 (2)
C1—N1—N2—V1	168.9 (2)	C10—N6—C11—N5	0.2 (4)
Ag1—N1—N2—V1	−12.7 (3)	C12A—N6—C11—N5	−179.2 (10)
C10—N4—N5—C11	−0.4 (4)	C12—N6—C11—N5	−178.1 (7)
Ag1—N4—N5—C11	177.9 (2)	C10—N6—C12—C13	−120.7 (10)
C10—N4—N5—Ag1ⁱ	166.2 (2)	C11—N6—C12—C13	57.3 (15)
Ag1—N4—N5—Ag1ⁱ	−15.5 (4)	N6—C12—C13—C18	−101.7 (13)
N2—N1—C1—N3	1.3 (3)	N6—C12—C13—C14	77.8 (15)
Ag1—N1—C1—N3	−176.8 (2)	C18—C13—C14—C15	0.4 (10)
C2—N3—C1—N1	−1.4 (3)	C12—C13—C14—C15	−179.1 (13)
C3—N3—C1—N1	−172.8 (3)	C13—C14—C15—C16	0.1 (13)
N1—N2—C2—N3	−0.2 (3)	C14—C15—C16—C17	−1.3 (15)
V1—N2—C2—N3	−169.37 (19)	C15—C16—C17—C18	1.8 (15)
C1—N3—C2—N2	1.0 (3)	C14—C13—C18—C17	0.0 (10)
C3—N3—C2—N2	172.5 (3)	C12—C13—C18—C17	179.5 (15)
C1—N3—C3—C4	−128.2 (3)	C16—C17—C18—C13	−1.1 (13)
C2—N3—C3—C4	62.2 (4)	C10—N6—C12A—C13A	−113 (2)
N3—C3—C4—C5	68.5 (4)	C11—N6—C12A—C13A	66 (3)
N3—C3—C4—C9	−116.6 (3)	N6—C12A—C13A—C14A	62 (4)
C9—C4—C5—C6	−1.7 (5)	N6—C12A—C13A—C18A	−117 (2)
C3—C4—C5—C6	173.3 (3)	C18A—C13A—C14A—C15A	0.0
C4—C5—C6—C7	0.5 (6)	C12A—C13A—C14A—C15A	−179 (3)
C5—C6—C7—C8	0.9 (7)	C13A—C14A—C15A—C16A	0.0
C6—C7—C8—C9	−1.1 (7)	C14A—C15A—C16A—C17A	0.0
C7—C8—C9—C4	−0.1 (7)	C15A—C16A—C17A—C18A	0.0
C5—C4—C9—C8	1.5 (5)	C16A—C17A—C18A—C13A	0.0
C3—C4—C9—C8	−173.6 (4)	C14A—C13A—C18A—C17A	0.0
N5—N4—C10—N6	0.5 (4)	C12A—C13A—C18A—C17A	179 (2)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱⁱ	0.93	2.44	3.289 (4)	153
C1—H1···F2ⁱⁱⁱ	0.93	2.63	3.108 (4)	113
C2—H2···F1^iv	0.93	2.07	2.935 (4)	154
C2—H2···F2^iv	0.93	2.60	3.304 (4)	133
C3—H3A···O1ⁱⁱⁱ	0.97	2.73	3.465 (4)	133
C3—H3B···F2ⁱⁱⁱ	0.97	2.37	3.006 (4)	123
C10—H10···O2	0.93	2.16	3.082 (4)	170
C11—H11···F1^v	0.93	2.07	2.935 (4)	153
C12—H12A···O1^v	0.97	2.65	3.388 (2)	133
C16—H16···O2^vi	0.93	2.42	3.339 (9)	172
C18—H18···O1^v	0.93	2.83	3.589 (15)	139

Symmetry codes: (ii) x−1, y, z; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+1, −z; (vi) x, −y+3/2, z−1/2.

Funding information

Funding for this research was provided by: National Research Foundation of Ukraine (Project No. 2020.20/0071).

References

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