research communications
μ-3-carboxy-1-(1,2,4-triazol-4-yl)adamantane-κ2N1:N2]tetrafluoridodi-μ2-oxido-dioxidodisilver(I)divanadium(V) tetrahydrate
of tetrakis[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
The 2{VO2F2}2(C13H17N3O2)4]·4H2O, supported by the heterofunctional ligand tr-ad-COOH [1-(1,2,4-triazol-4-yl)-3-carboxyadamantane] is reported. Four 1,2,4-triazole groups of the ligand link two AgI atoms, as well as AgI and VV centres, forming the heterobimetallic coordination cluster {AgI2(VVO2F2)2(tr)4}. VV exists as a vanadium oxofluoride anion and possesses a distorted trigonal–bipyramidal coordination environment [VO2F2N]. A carboxylic acid of the ligand stays in a neutral form and is involved in hydrogen bonding with solvent water molecules and VO2F2− ions of adjacent molecules. The extended hydrogen-bonding network is responsible for the crystal packing in the structure.
of the title molecular complex, [AgKeywords: crystal structure; 1,2,4-triazole; silver(I); vanadium(V) oxofluoride; heterobimetallic complex; hydrogen bonding.
CCDC reference: 1915603
1. Chemical context
Heterometallic hybrids incorporating a metal oxide/oxofluoride matrix are of particular interest as they exhibit non-trivial magnetic, luminescent (Cui et al., 2012), optical and catalytic properties (Dolbecq et al., 2010). Among the broad range of inorganic anions, vanadium oxofluorides (VOFs) stand out for their large number of types and structural motifs from mono- (Aldous et al., 2007; Stephens et al., 2005) to polynuclear (Buchholz et al., 1988; Ninclaus et al., 1997) ones in the structure as discrete units or incorporated into coordination frameworks (Welk et al., 2007; Mahenthirarajah et al., 2008). The AgI/VOF pair is a non-typical combination for classical coordination chemistry, but materials such as Ag4V2O6F2 (Sorensen et al., 2005; Albrecht et al., 2009) and Ag3VO2F4 (Chamberlain et al., 2010) are attractive electrochemically active phases for solid-state batteries.
In the present research we introduce a new ligand [tr-ad-COOH = 1-(1,2,4-triazol-4-yl)-3-carboxyadamantane], whose 1,2,4-triazole and –COOH donor groups can support the formation of the Ag–V heterometallic coordination cluster. It has recently been shown (Senchyk et al., 2012) that symmetrical 1,2,4-triazoles can selectively bridge these different metals. Considering a possible step-by-step mechanism, it becomes clear that after the formation of the simplest {Ag2(η2-tr)2(tr)2}2+ binuclear fragment, two N atoms remain uncoordinated and have potential for further interactions. In aqueous reaction media, vanadium oxofluorides exist in anionic forms with weakly coordinated water molecules that are very labile toward N-donor ligand substitution. Thus, a combination of an AgI–triazole cation and VOF anions lead to the neutral tetranuclear {AgI2(VVO2F2)2(tr)4} unit, which was found in the structure of the title [Ag2(VO2F2)2(tr-ad-COOH)4]·4H2O complex I (Fig. 1).
2. Structural commentary
The I cation, one [VO2F2]− anion, two organic ligands and two solvent water molecules. Two silver ions, two VOF anions and four tr-ad-COOH units constitute the molecular tetranuclear cluster, which resides across an inversion centre (Fig. 1). The AgI atom adopts a distorted tetrahedral coordination environment [AgN3O] with typical Ag—N(triazole) bond lengths [2.230 (3)–2.262 (3) Å; Table 1] and an elongated Ag—O bond [2.700 (3) Å]. Two 1,2,4-triazole functional groups link two adjacent silver atoms [the Ag⋯Agi distance is 3.7488 (5) Å; symmetry code: (i) –x, −y + 1, −z], while the other two 1,2,4-triazole groups combine the Ag and V centres [Ag⋯V= 3.5376 (6) Å]. The VV atom possesses a distorted trigonal–bipyramidal coordination environment [VO2F2N] with short V—O bonds [1.627 (2), 1.628 (2) Å], V—F bonds [1.839 (2), 1.850 (2) Å] and an elongated V—N bond [2.152 (3) Å]. The polyhedra can be more precisely described by the Reedijk's factor τ (Addison et al., 1984) of 0.72 (for strict square-pyramidal polyhedra τ = 0 and for trigonal–bipyramidal τ = 1).
of the title compound contains one AgAs a result, the heterobimetallic unit {AgI2(VVO2F2)2(tr)4} is formed. A search in the Cambridge Structural Database (version 5.39, updates of May 2018; Groom et al., 2016) shows that only three crystal structures containing the AgI/tr/VV fragments are known so far (Senchyk et al., 2012). While considering heterofunctional ligands, {Cu2(HL)2[Mo4O13]}·2H2O (H2L = 5-triazole isophthalic acid; Zhu et al., 2012) is the only known structure where both COO− and triazole groups support the heterometallic Cu⋯Mo connection.
3. Supramolecular features
The structure of I is characterized by an extended hydrogen-bonding network. The carboxylic function of the tr-ad-COOH ligand remains in a neutral form, being uncoordinated. It is involved in hydrogen bonding that leads to a three-dimensional hydrogen-bonded network (Figs. 2 and 3). The nearest environment of the molecular fragment complex involved in hydrogen-bonding interactions is shown in Fig. 4. The corresponding geometric parameters are given in Table 2. One carboxylic group, as a hydrogen-bond donor, forms a contact with a water molecule O3—H1O⋯O2Wiv = 2.650 (4) Å [symmetry code: (iv) x, 1 + y, z], while another COOH group, as a hydrogen-bond acceptor, is directed toward the F atom of a {VO2F2} anion [O5—H2O⋯F1v = 2.589 (3) Å; symmetry code: (v) 1 + x, −1 + y, z]. Two water molecules are interbonded [O2W—H3W⋯O1W = 2.753 (4) Å] and additionally act as hydrogen-bond donors with O and F atoms from the neighboring {VO2F2} anions and as hydrogen-bond acceptor (in the case of O2W ) with the O3 atom from an adjacent carboxylic group. Some weak contacts between the triazole C—H groups and F atoms of the VOF anions are also observed.
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4. Synthesis and crystallization
1-(1,2,4-Triazol-4-yl)-3-carboxyadamantane (tr-ad-COOH) was synthesized in 63% yield by refluxing 3-amino-adamantane-1-carboxylic acid (Wanka et al., 2007) (3.00 g, 15.4 mmol) and dimethylformamide azine (5.46 g, 38.5 mmol) in the presence of toluenesulfonic acid monohydrate (0.44 g, 2.3 mmol) as catalyst in DMF (30 ml). Complex I was prepared under hydrothermal conditions as follows. A mixture of AgOAc (16.7 mg, 0.100 mmol), tr-ad-COOH (12.4 mg, 0.050 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 14.8 mg, 78%).
5. Refinement
Crystal data, data collection and structure . The non-H atoms were refined with anisotropic displacement parameters and a soft rigid-bond restraint was applied to C10—C13 in order to improve the stability. C-bound hydrogen atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å (triazole), C—H = 0.97 Å (adamantane CH2), C—H = 0.98 Å (adamantane CH) and with Uiso(H) = 1.2Ueq(C). O-bound hydrogen atoms were located in a difference-Fourier map and then refined with O—H = 0.82 Å (carboxylic) or 0.85 Å (H2O) with Uiso(H) = 1.5Ueq(O).
details are summarized in Table 3
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Supporting information
CCDC reference: 1915603
https://doi.org/10.1107/S2056989019006844/zq2246sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019006844/zq2246Isup2.hkl
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012).[Ag2V2F4O4(C13H17N3O2)4]·4H2O | Z = 1 |
Mr = 1518.86 | F(000) = 776 |
Triclinic, P1 | Dx = 1.697 Mg m−3 |
a = 8.2673 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.6026 (6) Å | Cell parameters from 25045 reflections |
c = 14.6757 (7) Å | θ = 1.7–28.7° |
α = 77.985 (3)° | µ = 1.05 mm−1 |
β = 86.535 (2)° | T = 296 K |
γ = 83.945 (3)° | Prism, light-yellow |
V = 1486.05 (14) Å3 | 0.26 × 0.12 × 0.10 mm |
Bruker APEXII area-detector diffractometer | 4839 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.053 |
ω scans | θmax = 28.7°, θmin = 1.7° |
Absorption correction: numerical [face indexed (SADABS; Bruker, 2008)] | h = −11→11 |
Tmin = 0.682, Tmax = 0.890 | k = −16→17 |
25045 measured reflections | l = −19→19 |
7659 independent reflections |
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)] = 0.045 | Hydrogen site location: mixed |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0428P)2 + 0.1791P] where P = (Fo2 + 2Fc2)/3 |
7659 reflections | (Δ/σ)max = 0.001 |
397 parameters | Δρmax = 0.58 e Å−3 |
1 restraint | Δρmin = −0.70 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Ag1 | −0.00385 (4) | 0.54697 (2) | 0.11326 (2) | 0.04628 (11) | |
V1 | −0.30899 (7) | 0.54308 (4) | 0.29331 (4) | 0.03150 (14) | |
F1 | −0.3693 (3) | 0.67346 (15) | 0.21335 (14) | 0.0467 (5) | |
F2 | −0.5052 (3) | 0.49964 (18) | 0.26987 (17) | 0.0604 (6) | |
O1 | −0.1839 (3) | 0.44852 (18) | 0.26017 (19) | 0.0480 (7) | |
O2 | −0.3264 (3) | 0.5279 (2) | 0.40630 (16) | 0.0465 (6) | |
O3 | 0.1863 (4) | 1.1178 (2) | 0.3251 (2) | 0.0763 (10) | |
H1O | 0.1652 | 1.1836 | 0.3210 | 0.114* | |
O4 | 0.2087 (4) | 1.1221 (2) | 0.4731 (2) | 0.0697 (9) | |
O5 | 0.7345 (4) | −0.1354 (2) | 0.1879 (2) | 0.0763 (10) | |
H2O | 0.7008 | −0.1957 | 0.1971 | 0.114* | |
O6 | 0.4929 (4) | −0.0858 (2) | 0.1313 (2) | 0.0754 (10) | |
N1 | −0.0998 (3) | 0.6295 (2) | 0.29829 (18) | 0.0340 (6) | |
N2 | 0.0147 (4) | 0.6413 (2) | 0.2265 (2) | 0.0422 (7) | |
N3 | 0.0900 (3) | 0.7190 (2) | 0.33460 (18) | 0.0324 (6) | |
N4 | 0.2080 (4) | 0.4410 (2) | 0.0703 (2) | 0.0412 (7) | |
N5 | 0.2061 (4) | 0.4050 (2) | −0.0112 (2) | 0.0444 (8) | |
N6 | 0.4209 (4) | 0.3254 (2) | 0.06259 (18) | 0.0356 (7) | |
C1 | −0.0521 (4) | 0.6773 (3) | 0.3618 (2) | 0.0374 (8) | |
H1 | −0.1086 | 0.6817 | 0.4178 | 0.045* | |
C2 | 0.1274 (5) | 0.6938 (3) | 0.2511 (2) | 0.0425 (9) | |
H2 | 0.2212 | 0.7114 | 0.2153 | 0.051* | |
C3 | 0.1904 (4) | 0.7734 (2) | 0.3894 (2) | 0.0290 (7) | |
C4 | 0.1587 (5) | 0.7283 (3) | 0.4921 (2) | 0.0385 (8) | |
H4A | 0.1819 | 0.6497 | 0.5054 | 0.046* | |
H4B | 0.0455 | 0.7457 | 0.5095 | 0.046* | |
C5 | 0.2693 (5) | 0.7795 (3) | 0.5474 (3) | 0.0496 (10) | |
H5 | 0.2521 | 0.7500 | 0.6141 | 0.059* | |
C6 | 0.4463 (5) | 0.7555 (3) | 0.5197 (3) | 0.0600 (12) | |
H6A | 0.5146 | 0.7876 | 0.5560 | 0.072* | |
H6B | 0.4752 | 0.6773 | 0.5322 | 0.072* | |
C7 | 0.4743 (4) | 0.8014 (3) | 0.4181 (3) | 0.0475 (10) | |
H7 | 0.5890 | 0.7852 | 0.4003 | 0.057* | |
C8 | 0.3671 (4) | 0.7488 (3) | 0.3614 (3) | 0.0472 (10) | |
H8A | 0.3852 | 0.7775 | 0.2954 | 0.057* | |
H8B | 0.3953 | 0.6706 | 0.3731 | 0.057* | |
C9 | 0.1443 (4) | 0.8964 (2) | 0.3674 (2) | 0.0352 (8) | |
H9A | 0.0301 | 0.9124 | 0.3837 | 0.042* | |
H9B | 0.1622 | 0.9251 | 0.3013 | 0.042* | |
C10 | 0.2513 (4) | 0.9494 (3) | 0.4246 (3) | 0.0380 (8) | |
C11 | 0.2249 (5) | 0.9011 (3) | 0.5283 (2) | 0.0461 (9) | |
H11A | 0.2915 | 0.9345 | 0.5646 | 0.055* | |
H11B | 0.1118 | 0.9165 | 0.5471 | 0.055* | |
C12 | 0.4305 (4) | 0.9237 (3) | 0.3956 (3) | 0.0415 (9) | |
H12A | 0.4475 | 0.9512 | 0.3292 | 0.050* | |
H12B | 0.4999 | 0.9590 | 0.4287 | 0.050* | |
C13 | 0.2125 (5) | 1.0721 (3) | 0.4106 (3) | 0.0514 (10) | |
C14 | 0.3380 (5) | 0.3922 (3) | 0.1122 (2) | 0.0423 (9) | |
H14 | 0.3691 | 0.4026 | 0.1693 | 0.051* | |
C15 | 0.3337 (5) | 0.3364 (3) | −0.0129 (3) | 0.0519 (10) | |
H15 | 0.3613 | 0.2993 | −0.0610 | 0.062* | |
C16 | 0.5697 (4) | 0.2489 (2) | 0.0852 (2) | 0.0328 (7) | |
C17 | 0.6483 (5) | 0.2732 (3) | 0.1687 (3) | 0.0447 (9) | |
H17A | 0.5725 | 0.2647 | 0.2223 | 0.054* | |
H17B | 0.6772 | 0.3476 | 0.1550 | 0.054* | |
C18 | 0.8018 (5) | 0.1935 (3) | 0.1904 (3) | 0.0467 (9) | |
H18 | 0.8533 | 0.2085 | 0.2442 | 0.056* | |
C19 | 0.7547 (5) | 0.0767 (3) | 0.2133 (2) | 0.0421 (9) | |
H19A | 0.6806 | 0.0671 | 0.2675 | 0.050* | |
H19B | 0.8511 | 0.0263 | 0.2275 | 0.050* | |
C20 | 0.6725 (4) | 0.0529 (3) | 0.1294 (2) | 0.0376 (8) | |
C21 | 0.5206 (4) | 0.1337 (2) | 0.1075 (2) | 0.0337 (7) | |
H21A | 0.4677 | 0.1192 | 0.0547 | 0.040* | |
H21B | 0.4442 | 0.1251 | 0.1607 | 0.040* | |
C22 | 0.6886 (5) | 0.2630 (3) | 0.0006 (3) | 0.0471 (9) | |
H22A | 0.7184 | 0.3373 | −0.0144 | 0.057* | |
H22B | 0.6376 | 0.2488 | −0.0528 | 0.057* | |
C23 | 0.8418 (5) | 0.1830 (3) | 0.0231 (3) | 0.0516 (10) | |
H23 | 0.9186 | 0.1920 | −0.0308 | 0.062* | |
C24 | 0.9208 (5) | 0.2080 (3) | 0.1068 (3) | 0.0599 (12) | |
H24A | 1.0189 | 0.1592 | 0.1209 | 0.072* | |
H24B | 0.9507 | 0.2822 | 0.0923 | 0.072* | |
C25 | 0.7922 (5) | 0.0670 (3) | 0.0448 (3) | 0.0464 (9) | |
H25A | 0.8878 | 0.0156 | 0.0578 | 0.056* | |
H25B | 0.7414 | 0.0525 | −0.0087 | 0.056* | |
C26 | 0.6226 (5) | −0.0622 (3) | 0.1493 (3) | 0.0476 (9) | |
O1W | 0.2476 (3) | 0.4641 (2) | 0.4048 (2) | 0.0595 (7) | |
H1W | 0.3296 | 0.4786 | 0.3682 | 0.089* | |
H2W | 0.2773 | 0.4552 | 0.4606 | 0.089* | |
O2W | 0.1186 (3) | 0.33128 (19) | 0.3067 (2) | 0.0564 (7) | |
H3W | 0.1261 | 0.3502 | 0.3585 | 0.085* | |
H4W | 0.0243 | 0.3540 | 0.2866 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0503 (2) | 0.05347 (19) | 0.03972 (17) | 0.00170 (14) | −0.00405 (13) | −0.02286 (13) |
V1 | 0.0352 (3) | 0.0265 (3) | 0.0343 (3) | −0.0065 (2) | −0.0035 (2) | −0.0074 (2) |
F1 | 0.0587 (14) | 0.0416 (11) | 0.0383 (12) | −0.0013 (10) | −0.0061 (10) | −0.0051 (9) |
F2 | 0.0451 (14) | 0.0697 (15) | 0.0759 (17) | −0.0204 (11) | −0.0034 (12) | −0.0285 (13) |
O1 | 0.0462 (16) | 0.0342 (13) | 0.0697 (18) | −0.0062 (11) | −0.0050 (13) | −0.0227 (12) |
O2 | 0.0495 (17) | 0.0532 (15) | 0.0348 (14) | −0.0085 (12) | −0.0027 (12) | −0.0022 (12) |
O3 | 0.118 (3) | 0.0406 (16) | 0.068 (2) | −0.0068 (17) | −0.011 (2) | −0.0057 (15) |
O4 | 0.073 (2) | 0.0575 (18) | 0.091 (2) | −0.0061 (15) | −0.0108 (18) | −0.0400 (17) |
O5 | 0.071 (2) | 0.0330 (15) | 0.122 (3) | −0.0048 (14) | −0.033 (2) | −0.0003 (16) |
O6 | 0.087 (3) | 0.0415 (16) | 0.098 (3) | −0.0194 (16) | −0.042 (2) | 0.0033 (16) |
N1 | 0.0354 (16) | 0.0372 (15) | 0.0336 (15) | −0.0097 (12) | −0.0004 (13) | −0.0142 (12) |
N2 | 0.0450 (19) | 0.0518 (18) | 0.0386 (17) | −0.0174 (14) | 0.0052 (14) | −0.0247 (14) |
N3 | 0.0341 (16) | 0.0340 (14) | 0.0333 (15) | −0.0084 (12) | 0.0039 (12) | −0.0151 (12) |
N4 | 0.0451 (19) | 0.0443 (17) | 0.0383 (17) | 0.0040 (14) | −0.0067 (14) | −0.0205 (14) |
N5 | 0.051 (2) | 0.0509 (18) | 0.0333 (16) | 0.0055 (15) | −0.0092 (14) | −0.0176 (14) |
N6 | 0.0435 (18) | 0.0344 (15) | 0.0306 (15) | 0.0008 (13) | −0.0052 (13) | −0.0112 (12) |
C1 | 0.033 (2) | 0.048 (2) | 0.0373 (19) | −0.0148 (16) | 0.0065 (15) | −0.0199 (16) |
C2 | 0.044 (2) | 0.057 (2) | 0.0333 (19) | −0.0212 (18) | 0.0093 (16) | −0.0190 (17) |
C3 | 0.0270 (17) | 0.0314 (16) | 0.0320 (17) | −0.0067 (13) | −0.0010 (13) | −0.0122 (13) |
C4 | 0.045 (2) | 0.0367 (18) | 0.0353 (19) | −0.0130 (16) | −0.0025 (16) | −0.0052 (15) |
C5 | 0.062 (3) | 0.056 (2) | 0.034 (2) | −0.022 (2) | −0.0089 (18) | −0.0061 (17) |
C6 | 0.053 (3) | 0.045 (2) | 0.084 (3) | −0.0065 (19) | −0.035 (2) | −0.004 (2) |
C7 | 0.026 (2) | 0.047 (2) | 0.074 (3) | −0.0029 (16) | −0.0016 (19) | −0.023 (2) |
C8 | 0.034 (2) | 0.045 (2) | 0.071 (3) | −0.0073 (16) | 0.0059 (19) | −0.0302 (19) |
C9 | 0.036 (2) | 0.0297 (17) | 0.041 (2) | −0.0064 (14) | −0.0068 (15) | −0.0066 (14) |
C10 | 0.0318 (19) | 0.0296 (16) | 0.055 (2) | −0.0063 (14) | −0.0107 (16) | −0.0106 (16) |
C11 | 0.038 (2) | 0.064 (2) | 0.047 (2) | −0.0129 (18) | 0.0019 (17) | −0.0321 (19) |
C12 | 0.035 (2) | 0.047 (2) | 0.048 (2) | −0.0184 (16) | 0.0010 (16) | −0.0160 (17) |
C13 | 0.047 (2) | 0.046 (2) | 0.064 (3) | −0.0117 (18) | −0.009 (2) | −0.013 (2) |
C14 | 0.049 (2) | 0.045 (2) | 0.036 (2) | 0.0040 (17) | −0.0082 (17) | −0.0179 (16) |
C15 | 0.059 (3) | 0.062 (2) | 0.038 (2) | 0.014 (2) | −0.0126 (19) | −0.0252 (19) |
C16 | 0.038 (2) | 0.0290 (16) | 0.0316 (18) | −0.0041 (14) | −0.0039 (15) | −0.0060 (13) |
C17 | 0.048 (2) | 0.040 (2) | 0.051 (2) | −0.0030 (17) | −0.0113 (18) | −0.0186 (17) |
C18 | 0.043 (2) | 0.048 (2) | 0.054 (2) | −0.0046 (17) | −0.0159 (19) | −0.0179 (18) |
C19 | 0.047 (2) | 0.043 (2) | 0.0346 (19) | −0.0016 (17) | −0.0086 (17) | −0.0043 (16) |
C20 | 0.048 (2) | 0.0289 (17) | 0.0357 (19) | −0.0026 (15) | −0.0043 (16) | −0.0056 (14) |
C21 | 0.040 (2) | 0.0335 (17) | 0.0282 (17) | −0.0083 (14) | −0.0034 (15) | −0.0059 (14) |
C22 | 0.051 (2) | 0.040 (2) | 0.045 (2) | −0.0083 (17) | 0.0041 (19) | 0.0047 (17) |
C23 | 0.041 (2) | 0.056 (2) | 0.051 (2) | −0.0020 (19) | 0.0122 (19) | −0.0001 (19) |
C24 | 0.038 (2) | 0.051 (2) | 0.087 (3) | −0.0087 (19) | −0.007 (2) | −0.002 (2) |
C25 | 0.050 (2) | 0.043 (2) | 0.044 (2) | 0.0071 (17) | 0.0032 (18) | −0.0120 (17) |
C26 | 0.057 (3) | 0.040 (2) | 0.046 (2) | −0.0025 (19) | −0.0149 (19) | −0.0088 (17) |
O1W | 0.0571 (19) | 0.0644 (18) | 0.0593 (19) | −0.0086 (14) | −0.0060 (14) | −0.0151 (14) |
O2W | 0.0617 (19) | 0.0372 (14) | 0.0679 (19) | 0.0009 (13) | −0.0066 (15) | −0.0072 (13) |
Ag1—N4 | 2.230 (3) | C8—H8A | 0.9700 |
Ag1—N2 | 2.257 (3) | C8—H8B | 0.9700 |
Ag1—N5i | 2.262 (3) | C9—C10 | 1.543 (4) |
Ag1—O1 | 2.700 (3) | C9—H9A | 0.9700 |
V1—O1 | 1.627 (2) | C9—H9B | 0.9700 |
V1—O2 | 1.628 (2) | C10—C13 | 1.519 (5) |
V1—F2 | 1.839 (2) | C10—C11 | 1.529 (5) |
V1—F1 | 1.850 (2) | C10—C12 | 1.536 (5) |
V1—N1 | 2.152 (3) | C11—H11A | 0.9700 |
O3—C13 | 1.288 (5) | C11—H11B | 0.9700 |
O3—H1O | 0.8200 | C12—H12A | 0.9700 |
O4—C13 | 1.214 (5) | C12—H12B | 0.9700 |
O5—C26 | 1.301 (4) | C14—H14 | 0.9300 |
O5—H2O | 0.8200 | C15—H15 | 0.9300 |
O6—C26 | 1.201 (5) | C16—C21 | 1.513 (4) |
N1—C1 | 1.309 (4) | C16—C17 | 1.521 (4) |
N1—N2 | 1.368 (4) | C16—C22 | 1.528 (5) |
N2—C2 | 1.306 (4) | C17—C18 | 1.539 (5) |
N3—C2 | 1.339 (4) | C17—H17A | 0.9700 |
N3—C1 | 1.342 (4) | C17—H17B | 0.9700 |
N3—C3 | 1.496 (4) | C18—C24 | 1.519 (6) |
N4—C14 | 1.301 (4) | C18—C19 | 1.526 (5) |
N4—N5 | 1.367 (4) | C18—H18 | 0.9800 |
N5—C15 | 1.293 (4) | C19—C20 | 1.539 (5) |
N5—Ag1i | 2.262 (3) | C19—H19A | 0.9700 |
N6—C15 | 1.334 (4) | C19—H19B | 0.9700 |
N6—C14 | 1.335 (4) | C20—C26 | 1.514 (5) |
N6—C16 | 1.489 (4) | C20—C25 | 1.533 (5) |
C1—H1 | 0.9300 | C20—C21 | 1.536 (5) |
C2—H2 | 0.9300 | C21—H21A | 0.9700 |
C3—C8 | 1.512 (4) | C21—H21B | 0.9700 |
C3—C4 | 1.513 (4) | C22—C23 | 1.540 (5) |
C3—C9 | 1.529 (4) | C22—H22A | 0.9700 |
C4—C5 | 1.531 (5) | C22—H22B | 0.9700 |
C4—H4A | 0.9700 | C23—C25 | 1.525 (5) |
C4—H4B | 0.9700 | C23—C24 | 1.528 (6) |
C5—C11 | 1.509 (5) | C23—H23 | 0.9800 |
C5—C6 | 1.512 (6) | C24—H24A | 0.9700 |
C5—H5 | 0.9800 | C24—H24B | 0.9700 |
C6—C7 | 1.496 (6) | C25—H25A | 0.9700 |
C6—H6A | 0.9700 | C25—H25B | 0.9700 |
C6—H6B | 0.9700 | O1W—H1W | 0.8500 |
C7—C12 | 1.517 (5) | O1W—H2W | 0.8500 |
C7—C8 | 1.535 (5) | O2W—H3W | 0.8499 |
C7—H7 | 0.9800 | O2W—H4W | 0.8500 |
N4—Ag1—N2 | 121.35 (11) | C11—C10—C9 | 109.4 (3) |
N4—Ag1—N5i | 115.91 (10) | C12—C10—C9 | 108.4 (3) |
N2—Ag1—N5i | 120.21 (11) | C5—C11—C10 | 110.3 (3) |
N4—Ag1—O1 | 114.33 (9) | C5—C11—H11A | 109.6 |
N2—Ag1—O1 | 74.30 (9) | C10—C11—H11A | 109.6 |
N5i—Ag1—O1 | 97.45 (10) | C5—C11—H11B | 109.6 |
O1—V1—O2 | 112.52 (13) | C10—C11—H11B | 109.6 |
O1—V1—F2 | 100.53 (11) | H11A—C11—H11B | 108.1 |
O2—V1—F2 | 100.10 (12) | C7—C12—C10 | 109.5 (3) |
O1—V1—F1 | 122.01 (12) | C7—C12—H12A | 109.8 |
O2—V1—F1 | 122.74 (11) | C10—C12—H12A | 109.8 |
F2—V1—F1 | 86.60 (10) | C7—C12—H12B | 109.8 |
O1—V1—N1 | 87.04 (11) | C10—C12—H12B | 109.8 |
O2—V1—N1 | 87.42 (12) | H12A—C12—H12B | 108.2 |
F2—V1—N1 | 166.19 (11) | O4—C13—O3 | 123.5 (4) |
F1—V1—N1 | 79.59 (10) | O4—C13—C10 | 123.6 (4) |
V1—O1—Ag1 | 107.06 (11) | O3—C13—C10 | 112.9 (3) |
C13—O3—H1O | 109.5 | N4—C14—N6 | 111.3 (3) |
C26—O5—H2O | 109.5 | N4—C14—H14 | 124.3 |
C1—N1—N2 | 107.1 (3) | N6—C14—H14 | 124.3 |
C1—N1—V1 | 131.9 (2) | N5—C15—N6 | 111.9 (3) |
N2—N1—V1 | 120.97 (19) | N5—C15—H15 | 124.0 |
C2—N2—N1 | 106.5 (3) | N6—C15—H15 | 124.0 |
C2—N2—Ag1 | 134.6 (2) | N6—C16—C21 | 108.4 (3) |
N1—N2—Ag1 | 117.65 (19) | N6—C16—C17 | 109.7 (3) |
C2—N3—C1 | 104.9 (3) | C21—C16—C17 | 110.0 (3) |
C2—N3—C3 | 127.8 (3) | N6—C16—C22 | 108.9 (3) |
C1—N3—C3 | 127.2 (3) | C21—C16—C22 | 109.9 (3) |
C14—N4—N5 | 106.5 (3) | C17—C16—C22 | 110.0 (3) |
C14—N4—Ag1 | 133.2 (2) | C16—C17—C18 | 108.7 (3) |
N5—N4—Ag1 | 119.9 (2) | C16—C17—H17A | 110.0 |
C15—N5—N4 | 106.3 (3) | C18—C17—H17A | 110.0 |
C15—N5—Ag1i | 129.4 (2) | C16—C17—H17B | 110.0 |
N4—N5—Ag1i | 124.1 (2) | C18—C17—H17B | 110.0 |
C15—N6—C14 | 103.9 (3) | H17A—C17—H17B | 108.3 |
C15—N6—C16 | 125.8 (3) | C24—C18—C19 | 109.8 (3) |
C14—N6—C16 | 130.2 (3) | C24—C18—C17 | 109.7 (3) |
N1—C1—N3 | 110.4 (3) | C19—C18—C17 | 109.5 (3) |
N1—C1—H1 | 124.8 | C24—C18—H18 | 109.3 |
N3—C1—H1 | 124.8 | C19—C18—H18 | 109.3 |
N2—C2—N3 | 111.0 (3) | C17—C18—H18 | 109.3 |
N2—C2—H2 | 124.5 | C18—C19—C20 | 109.5 (3) |
N3—C2—H2 | 124.5 | C18—C19—H19A | 109.8 |
N3—C3—C8 | 107.8 (2) | C20—C19—H19A | 109.8 |
N3—C3—C4 | 108.5 (2) | C18—C19—H19B | 109.8 |
C8—C3—C4 | 110.8 (3) | C20—C19—H19B | 109.8 |
N3—C3—C9 | 109.8 (3) | H19A—C19—H19B | 108.2 |
C8—C3—C9 | 109.8 (3) | C26—C20—C25 | 109.0 (3) |
C4—C3—C9 | 110.1 (3) | C26—C20—C21 | 109.1 (3) |
C3—C4—C5 | 108.1 (3) | C25—C20—C21 | 109.3 (3) |
C3—C4—H4A | 110.1 | C26—C20—C19 | 111.2 (3) |
C5—C4—H4A | 110.1 | C25—C20—C19 | 109.0 (3) |
C3—C4—H4B | 110.1 | C21—C20—C19 | 109.1 (3) |
C5—C4—H4B | 110.1 | C16—C21—C20 | 109.5 (3) |
H4A—C4—H4B | 108.4 | C16—C21—H21A | 109.8 |
C11—C5—C6 | 109.7 (3) | C20—C21—H21A | 109.8 |
C11—C5—C4 | 108.6 (3) | C16—C21—H21B | 109.8 |
C6—C5—C4 | 110.9 (3) | C20—C21—H21B | 109.8 |
C11—C5—H5 | 109.2 | H21A—C21—H21B | 108.2 |
C6—C5—H5 | 109.2 | C16—C22—C23 | 109.2 (3) |
C4—C5—H5 | 109.2 | C16—C22—H22A | 109.8 |
C7—C6—C5 | 109.6 (3) | C23—C22—H22A | 109.8 |
C7—C6—H6A | 109.7 | C16—C22—H22B | 109.8 |
C5—C6—H6A | 109.7 | C23—C22—H22B | 109.8 |
C7—C6—H6B | 109.7 | H22A—C22—H22B | 108.3 |
C5—C6—H6B | 109.7 | C25—C23—C24 | 110.7 (3) |
H6A—C6—H6B | 108.2 | C25—C23—C22 | 108.8 (3) |
C6—C7—C12 | 111.3 (3) | C24—C23—C22 | 108.8 (3) |
C6—C7—C8 | 109.2 (3) | C25—C23—H23 | 109.5 |
C12—C7—C8 | 108.2 (3) | C24—C23—H23 | 109.5 |
C6—C7—H7 | 109.3 | C22—C23—H23 | 109.5 |
C12—C7—H7 | 109.3 | C18—C24—C23 | 109.4 (3) |
C8—C7—H7 | 109.3 | C18—C24—H24A | 109.8 |
C3—C8—C7 | 109.2 (3) | C23—C24—H24A | 109.8 |
C3—C8—H8A | 109.8 | C18—C24—H24B | 109.8 |
C7—C8—H8A | 109.8 | C23—C24—H24B | 109.8 |
C3—C8—H8B | 109.8 | H24A—C24—H24B | 108.2 |
C7—C8—H8B | 109.8 | C23—C25—C20 | 109.5 (3) |
H8A—C8—H8B | 108.3 | C23—C25—H25A | 109.8 |
C3—C9—C10 | 108.1 (3) | C20—C25—H25A | 109.8 |
C3—C9—H9A | 110.1 | C23—C25—H25B | 109.8 |
C10—C9—H9A | 110.1 | C20—C25—H25B | 109.8 |
C3—C9—H9B | 110.1 | H25A—C25—H25B | 108.2 |
C10—C9—H9B | 110.1 | O6—C26—O5 | 122.0 (4) |
H9A—C9—H9B | 108.4 | O6—C26—C20 | 124.2 (4) |
C13—C10—C11 | 107.8 (3) | O5—C26—C20 | 113.8 (3) |
C13—C10—C12 | 109.3 (3) | H1W—O1W—H2W | 108.4 |
C11—C10—C12 | 109.1 (3) | H3W—O2W—H4W | 108.4 |
C13—C10—C9 | 112.9 (3) | ||
O2—V1—O1—Ag1 | −138.31 (12) | C11—C10—C13—O4 | 19.2 (5) |
F2—V1—O1—Ag1 | 116.01 (11) | C12—C10—C13—O4 | −99.3 (5) |
F1—V1—O1—Ag1 | 23.43 (16) | C9—C10—C13—O4 | 140.1 (4) |
N1—V1—O1—Ag1 | −52.34 (11) | C11—C10—C13—O3 | −161.8 (3) |
C1—N1—N2—C2 | 1.2 (4) | C12—C10—C13—O3 | 79.8 (4) |
V1—N1—N2—C2 | −178.1 (2) | C9—C10—C13—O3 | −40.9 (5) |
C1—N1—N2—Ag1 | 170.6 (2) | N5—N4—C14—N6 | −0.5 (4) |
V1—N1—N2—Ag1 | −8.7 (3) | Ag1—N4—C14—N6 | 171.8 (2) |
C14—N4—N5—C15 | 0.5 (4) | C15—N6—C14—N4 | 0.2 (4) |
Ag1—N4—N5—C15 | −173.0 (3) | C16—N6—C14—N4 | −175.9 (3) |
C14—N4—N5—Ag1i | 176.9 (2) | N4—N5—C15—N6 | −0.4 (5) |
Ag1—N4—N5—Ag1i | 3.4 (4) | Ag1i—N5—C15—N6 | −176.5 (2) |
N2—N1—C1—N3 | −0.5 (4) | C14—N6—C15—N5 | 0.1 (5) |
V1—N1—C1—N3 | 178.6 (2) | C16—N6—C15—N5 | 176.5 (3) |
C2—N3—C1—N1 | −0.3 (4) | C15—N6—C16—C21 | −68.7 (4) |
C3—N3—C1—N1 | −175.8 (3) | C14—N6—C16—C21 | 106.7 (4) |
N1—N2—C2—N3 | −1.4 (4) | C15—N6—C16—C17 | 171.2 (4) |
Ag1—N2—C2—N3 | −168.2 (2) | C14—N6—C16—C17 | −13.4 (5) |
C1—N3—C2—N2 | 1.1 (4) | C15—N6—C16—C22 | 50.7 (5) |
C3—N3—C2—N2 | 176.5 (3) | C14—N6—C16—C22 | −133.8 (4) |
C2—N3—C3—C8 | −26.6 (4) | N6—C16—C17—C18 | −179.8 (3) |
C1—N3—C3—C8 | 147.8 (3) | C21—C16—C17—C18 | 61.1 (4) |
C2—N3—C3—C4 | −146.7 (3) | C22—C16—C17—C18 | −60.0 (4) |
C1—N3—C3—C4 | 27.8 (4) | C16—C17—C18—C24 | 60.2 (4) |
C2—N3—C3—C9 | 92.9 (4) | C16—C17—C18—C19 | −60.4 (4) |
C1—N3—C3—C9 | −92.6 (4) | C24—C18—C19—C20 | −60.6 (4) |
N3—C3—C4—C5 | 176.8 (3) | C17—C18—C19—C20 | 59.9 (4) |
C8—C3—C4—C5 | 58.6 (4) | C18—C19—C20—C26 | −179.6 (3) |
C9—C3—C4—C5 | −63.0 (4) | C18—C19—C20—C25 | 60.2 (4) |
C3—C4—C5—C11 | 62.2 (4) | C18—C19—C20—C21 | −59.2 (4) |
C3—C4—C5—C6 | −58.4 (4) | N6—C16—C21—C20 | 179.0 (2) |
C11—C5—C6—C7 | −59.7 (4) | C17—C16—C21—C20 | −61.1 (4) |
C4—C5—C6—C7 | 60.2 (4) | C22—C16—C21—C20 | 60.1 (4) |
C5—C6—C7—C12 | 59.4 (4) | C26—C20—C21—C16 | −178.7 (3) |
C5—C6—C7—C8 | −60.1 (4) | C25—C20—C21—C16 | −59.6 (3) |
N3—C3—C8—C7 | −178.7 (3) | C19—C20—C21—C16 | 59.6 (4) |
C4—C3—C8—C7 | −60.1 (4) | N6—C16—C22—C23 | −179.2 (3) |
C9—C3—C8—C7 | 61.7 (4) | C21—C16—C22—C23 | −60.6 (4) |
C6—C7—C8—C3 | 60.1 (4) | C17—C16—C22—C23 | 60.5 (4) |
C12—C7—C8—C3 | −61.3 (4) | C16—C22—C23—C25 | 60.5 (4) |
N3—C3—C9—C10 | −179.6 (3) | C16—C22—C23—C24 | −60.2 (4) |
C8—C3—C9—C10 | −61.2 (4) | C19—C18—C24—C23 | 59.4 (4) |
C4—C3—C9—C10 | 61.0 (3) | C17—C18—C24—C23 | −61.0 (4) |
C3—C9—C10—C13 | −178.2 (3) | C25—C23—C24—C18 | −58.8 (4) |
C3—C9—C10—C11 | −58.2 (3) | C22—C23—C24—C18 | 60.7 (4) |
C3—C9—C10—C12 | 60.6 (3) | C24—C23—C25—C20 | 59.0 (4) |
C6—C5—C11—C10 | 60.2 (4) | C22—C23—C25—C20 | −60.6 (4) |
C4—C5—C11—C10 | −61.2 (4) | C26—C20—C25—C23 | 179.3 (3) |
C13—C10—C11—C5 | −177.3 (3) | C21—C20—C25—C23 | 60.1 (4) |
C12—C10—C11—C5 | −58.8 (4) | C19—C20—C25—C23 | −59.1 (4) |
C9—C10—C11—C5 | 59.6 (4) | C25—C20—C26—O6 | −104.9 (5) |
C6—C7—C12—C10 | −58.3 (4) | C21—C20—C26—O6 | 14.5 (5) |
C8—C7—C12—C10 | 61.7 (4) | C19—C20—C26—O6 | 134.9 (4) |
C13—C10—C12—C7 | 174.6 (3) | C25—C20—C26—O5 | 74.7 (4) |
C11—C10—C12—C7 | 57.0 (4) | C21—C20—C26—O5 | −166.0 (3) |
C9—C10—C12—C7 | −62.0 (4) | C19—C20—C26—O5 | −45.5 (5) |
Symmetry code: (i) −x, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···F2ii | 0.85 | 1.92 | 2.763 (4) | 169 |
O1W—H2W···O2iii | 0.85 | 2.08 | 2.910 (4) | 166 |
O2W—H3W···O1W | 0.85 | 2.08 | 2.753 (4) | 136 |
O2W—H4W···O1 | 0.85 | 2.00 | 2.813 (4) | 161 |
O3—H1O···O2Wiv | 0.82 | 1.83 | 2.650 (4) | 178 |
O5—H2O···F1v | 0.82 | 1.77 | 2.589 (3) | 178 |
C15—H15···F1i | 0.93 | 2.19 | 2.966 (4) | 141 |
C14—H14···F2ii | 0.93 | 2.44 | 3.303 (4) | 154 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x+1, y, z; (iii) −x, −y+1, −z+1; (iv) x, y+1, z; (v) x+1, y−1, z. |
Funding information
Funding for this research was provided by: the Ministry of Education and Science of Ukraine (grant No. 19BF037-05).
References
Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. CSD CrossRef Web of Science Google Scholar
Albrecht, T. A., Sauvage, F., Bodenez, V., Tarascon, J.-M. & Poeppelmeier, K. R. (2009). Chem. Mater. 21, 3017–3020. Web of Science CrossRef CAS Google Scholar
Aldous, D. W., Stephens, N. F. & Lightfoot, P. (2007). Dalton Trans. pp. 2271–2282. Web of Science CSD CrossRef Google Scholar
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Buchholz, N., Leimkuehler, M., Kiriazis, L. & Mattes, R. (1988). Inorg. Chem. 27, 2035–2039. CSD CrossRef CAS Web of Science Google Scholar
Chamberlain, J. M., Albrecht, T. A., Lesage, J., Sauvage, F., Stern, C. L. & Poeppelmeier, K. R. (2010). Cryst. Growth Des. 10, 4868–4873. Web of Science CrossRef ICSD CAS Google Scholar
Cui, Y., Yue, Y., Qian, G. & Chen, B. (2012). Chem. Rev. 112, 1126–1162. Web of Science CrossRef CAS PubMed Google Scholar
Dolbecq, A., Dumas, E., Mayer, C. R. & Mialane, P. (2010). Chem. Rev. 110, 6009–6048. Web of Science CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Mahenthirarajah, T., Li, Y. & Lightfoot, P. (2008). Inorg. Chem. 47, 9097–9102. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ninclaus, C., Riou, D. & Férey, G. (1997). Chem. Commun. pp. 851–852. CSD CrossRef Web of Science Google Scholar
Senchyk, G. A., Bukhan'ko, V. A., Lysenko, A. B., Krautscheid, H., Rusanov, E. B., Chernega, A. N., Karbowiak, M. & Domasevitch, K. V. (2012). Inorg. Chem. 51, 8025–8033. Web of Science CSD CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sorensen, E. M., Izumi, H. K., Vaughey, J. T., Stern, C. L. & Poeppelmeier, K. R. (2005). J. Am. Chem. Soc. 127, 6347–6352. Web of Science CrossRef ICSD PubMed CAS Google Scholar
Stephens, N. F., Buck, M. & Lightfoot, P. (2005). J. Mater. Chem. 15, 4298–4300. Web of Science CSD CrossRef CAS Google Scholar
Wanka, L., Cabrele, C., Vanejews, M. & Schreiner, P. R. (2007). Eur. J. Org. Chem. pp. 1474–1490. Web of Science CSD CrossRef Google Scholar
Welk, M. E., Stern, C. L., Poeppelmeier, K. R. & Norquist, A. J. (2007). Cryst. Growth Des. 7, 956–961. Web of Science CSD CrossRef CAS Google Scholar
Zhu, M., Su, S.-Q., Song, X.-Z., Hao, Z.-M., Song, S.-Y. & Zhang, H.-J. (2012). Dalton Trans. 41, 13267–13270. Web of Science CSD CrossRef CAS PubMed Google Scholar
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