Copper(I) Chloride π-Complexes with 2,5-Bis(Allylthio)-1,3,4-Thiadiazole: Synthesis and Structural Features

Article abstract of DOI:10.1134/S0022476618020191

Three new Cu(I) π-complexes with 2,5-bis(allylthio)-1,3,4-thiadizole (Bialtia) ([Cu₃Cl₃(Bialtia)₂] (1), [Cu₃Cl₃(Bialtia)] (2), and [Cu₂Cl₂(Bialtia)] (3)) are obtained by the alternating current electrochemical synthesis and studied by single crystal X-ray diffraction. A distinctive feature of Bialtia is its ability to coordinate to Cu(I) atoms by nitrogen atoms of the thiadiazole core and two allyl groups. The formation of island inorganic {Cu₃Cl₃} moieties occurs in 1 through π coordination of two independent Bialtia molecules by three metal atoms. Due to the absence of one Bialtia molecule in 2, inorganic {–Cu₃Cl₃–} subunits join into infinite chains {[Cu₃Cl₃(Bialtia)]}_n}. The structure of [Cu₂Cl₂(Bialtia)] (3) contains two Cu(I) atoms with different coordination environments: distorted tetrahedral and trigonal.

Full text of DOI:10.1134/S0022476618020191

Journal of Structural Chemistry. Vol. 59, No. 2, pp. 388-394, 2018.
Original Russian Text © 2018 Yu. I. Slyvka1, B. R. Ardan, M. G. Mys kiv.
COPPER(I) CHLORIDE π-COMPLEXES WITH
2,5-bis(ALLYLTHIO)-1,3,4-THIADIAZOLE:
SYNTHESIS AND STRUCTURAL FEATURES
Yu. I. Slyvka, B. R. Ardan, and M. G. Mys′kiv
Three new Cu(I) π-complexes with 2,5-bis(allylthio)-1,3,4-thiadizole (Bialtia) ([Cu Cl (Bialtia) ] (1),
3 3 2
[Cu Cl (Bialtia)]
3 3
(2),
and
[Cu Cl (Bialtia)]
2 2
(3))
are
obtained
by
the
alternating
current electrochemical synthesis and studied by single crystal X-ray diffraction. A distinctive feature of
Bialtia is its ability to coordinate to Cu(I) atoms by nitrogen atoms of the thiadiazole core and two allyl
3 3
groups. The formation of island inorganic {Cu Cl } moieties occurs in 1 through π coordination of two
independent Bialtia molecules by three metal atoms. Due to the absence of one Bialtia molecule in 2,
inorganic {–Cu Cl –} subunits join into infinite chains {[Cu Cl (Bialtia)]} . The structure of
3 3 3 3 n
2 2
[Cu Cl (Bialtia)] (3) contains two Cu(I) atoms with different coordination environments: distorted
tetrahedral and trigonal.
DOI: 10.1134/S0022476618020191
Keywords: copper(I) chloride, π-complex, 1,3,4-thiadiazole, allyl derivative, crystal structure.
Among multiple thiadiazole derivatives known to exist in four isomeric forms, 1,3,4-thiadiazoles are the most
studied class of compounds used in pharmacology, agriculture, and also as corrosion inhibitors, luminophores, and precursors
in the synthesis of transition metal organic compounds [1-4]. Although many 1,3,4-thiadiazoles, including their allyl
derivatives, were first obtained in the 19th century, until recently there were no any crystal structural information on their
copper(I) π-complexes in the literature [5, 6]. However, the alternating current electrochemical synthesis method enabled us
to prepare a series of Cu(I) π-complexes with 2-allylamino-5-methyl-1,3,4-thiadiazole (Mepeta), 2-allylamino-5-phenyl-
1
,3,4-thiadiazole (Phepeta), and 5-allylthio-1,3,4-thiadiazole-2-amine (Pesta), which were studied by single crystal X-ray
diffraction [6-9].
When there are simultaneously the 1,3,4-thiadiazole (or 1,2,3-triazole) core and a labile allyl group bonded to it
whose C=C bond acts as Pearson’s soft base [10]), it appears to be favorable for the selective involvement of atoms of
inorganic anions in Cu(І) coordination and promotes the formation of previously unknown inorganic moieties, in particular,
(
I
the Cu ⋯FSiF
2−
5
bonds [9, 11-13]. The prevailing tendency of the Mepeta and Pesta ligands to form dimeric
2+
2+
2 2 2 2
[Cu (Mepeta) ] and [Cu (Mepeta) ] moieties with their N,N,(C=C)-chelate bridging π,σ coordination to the copper(I) ion
was also established.
In order to study the coordination features of diallyl derivatives of 1,3,4-thiadiazoles, namely, 2,5-bis(allylthio)-
8 10 2 3
1,3,4-thiadizole C H N S (Bialtia), with respect to copper(I) chloride, three new π-complexes with the composition
Franko National University Lviv, Ukraine; y_slyvka@lnu.edu.ua. Translated from Zhurnal Strukturnoi Khimii, Vol.
9, No. 2, pp. 402-408, March-April, 2018. Original article submitted May 18, 2017.
5
388
0022-4766/18/5902-0388 © 2018 by Pleiades Publishing, Ltd.

[Cu
3 3 2 3 3 2 2
Cl (Bialtia) ] (1), [Cu Cl (Bialtia)] (2), and [Cu Cl (Bialtia)] (3) were synthesized and analyzed by single crystal X-ray
diffraction.
EXPERIMENTAL
Synthesis. 1,3,4-Thiadiazole-2,5-dithiol was obtained according to the known procedure from hydrazine sulfate and
carbon disulfide [14]. 2,5-Bis(allylthio)-1,3,4-thiadizole (Bialtia) was prepared by allylation of 1,3,4-thiadiazole-2,5-dithiol
3
with allyl chloride in the presence of NaHCO in an ethanol solution. The yield was 96%. 2,5-Bis(allylthio)-1,3,4-thiadizole
1
is a yellow liquid at room temperature. Bialtia: H NMR (Bruker Avance spectrometer, 500 MHz, MeOD) δ 5.97 ppm (ddt,
J = 17.0 Hz, 10.0 Hz, 7.0 Hz, 2H, =CH), 5.32 ppm (dd, J = 16.9 Hz, 1.2 Hz, 2H, CH =), 5.19 ppm (dd, J = 10.0 Hz, 0.5 Hz,
2
13
2
1
2 2
H, CH =), 3.89 ppm (d, J = 7.0 Hz, 4H, CH ). C NMR (126 MHz, MeOD) δ, 167.23 ppm (C-ring), 133.53 ppm (=CH),
19.91 ppm (CH =), 38.16 ppm (CH ).
2 2
[Cu
Cl (Bialtia)
3 3
2
] compound (1) was obtained as colorless prismatic crystals on copper electrodes by the alternating
current electrochemical synthesis [15] from 4 ml of an ethanol solution of 0.22 g (1.3 mmol) of CuCl
⋅2H O and 0.16 g
2 2
(0.7 mmol) of Bialtia in one day at the alternating current voltage of 0.4 V.
Single crystals of [Cu Cl (Bialtia)] (2) were also obtained by the alternating current electrochemical synthesis from
3 3
4
2 2
ml of an ethanol solution of 0.22 g (1.3 mmol) of CuCl ⋅2H O and 0.25 g (1.1 mmol) of Bialtia. Needle-shaped yellowish
crystals of 2 formed on copper electrodes in five days at the alternating current voltage of 0.6 V. When this reactor was kept
in a refrigerator at a temperature of –18 °C for two weeks, yellowish prismatic crystals (on the reactor bottom) of
[Cu Cl (Bialtia)] compound (3) formed.
2 2
Single crystal X-ray diffraction. A set of integrated reflection intensities for the crystals of compounds 1 and 3 was
measured on a Kuma KM-4-CCD single crystal diffractometer (MoK radiation, graphite monochromator, Mercury CCD
detector); and for the crystal of complex 2, on an Agilent Xcalibur (CuK radiation, graphite monochromator, Onyx CCD
α
α
2
detector). All three structures were solved and refined using the SHELXT and SHELXL software with the OLEX interface
[16-18]. The positional and thermal parameters of all non-hydrogen atoms (except for carbon C11, C12, and C13 atoms of the
2
disordered allyl group of the organic ligand in 2) for 1-3 were refined by the full-matrix least-squares method on F . In 1, the
Cu1 atom, together with C atoms of the allyl group coordinated to it, is disordered over two positions with their respective
occupancies of 0.833(5) (Cu1A, C12A, C13A) and 0.167(5) (Cu1B, C12B, C13B). In 2, carbon atoms of one of the allyl
groups are also disordered over two positions with their respective occupancies of 0.66(2) (C11А, C12A, C13A) and 0.34(2)
(C11B, C12B, C13B). The positions of hydrogen atoms were calculated geometrically and refined with a fixed C–H distance
and Uiso(H) = 1/2Ueq(C). Details of the single crystal X-ray diffraction and main crystal structural data for compounds 1-3 are
given in Table 1.
Atomic coordinates and other parameters of compounds 1-3 have been deposited with the Cambridge Structural
Database (Nos. CCDC 1543062-1543064 respectively) at the address of www.ccdc.cam.ac.uk/data_request/cif.
RESULTS AND DISCUSSION
3 3 2
[Cu Cl (Bialtia) ] π-complex (1) crystallizes in the triclinic crystal symmetry; the asymmetric unit of the structure
contains two organic ligand molecules and three independent copper and chlorine atoms. One of the Bialtia molecules acts as
the chelate-bridging π,σ ligand coordinating to the Cu(I) atom by two olefinic C=C bonds of two S-allyl groups and two N13
and N14 atoms of the 1,3,4-thiadiazole core (Fig. 1, Table 2). The Cu1 and Cu2 atoms have a similar distorted tetrahedral
environment consisting of the nitrogen atom, the olefinic bond, and two bridging chlorine atoms (τ
4
= 0.82 for Cu1A,
= 0.80 for Cu2) [19, 20]. The Cl1 atom, on the one hand, joins Cu1 and Cu2 in a five-membered
N Cu Cl} ring and, on the other hand, together with two other bridging Cl2 and Cl3 atoms, enters into the coordination
4 4
τ = 0.84 for Cu1B, and τ
{
2
2
389

TABLE 1. Details of Single Crystal X-Ray Diffraction and the Main Crystal Structural Data for Compounds 1-3
Characteristic
1
2
3
Empirical formula
М, g/mol
C
16
H
20Cl
3
Cu
757.69
150(2)
3
N
S
4 6
C
8
H
10Cl
3
Cu
527.33
120(2)
3
N
S
2 3
C
8
H
10Cl
2
Cu
428.34
150(2)
2 2 3
N S
T, K
Crystal symmetry
Radiation
Triclinic
Orthorhombic
Orthorhombic
MoK
α
CuK
α
MoK
α
Space group
P2
1
2
2
1 1
Pca2
1
P1
Unit cell parameters
a, Å
b, Å
9.863(3)
9.937(3)
8.328(3)
10.495(4)
16.733(5)
90
11.033(4)
8.345(3)
14.382(4)
90
c, Å
14.138(4)
78.63(3)
88.30(3)
70.42(3)
1278.9(7)
2
α, deg
β, deg
γ, deg
90
90
90
90
3
V, Å
1462.5(9)
4
1324.2(8)
4
Z
3
ρcalc, g/cm
1.97
2.40
2.15
–
1
μ, mm
F(000)
Crystal size, mm
3.29
13.98
1032
4.06
756
848
0.39×0.20×0.12
2.9 ÷ 36.8
0.56×0.12×0.10
6.8 ÷ 89.1
–10 ≤ h ≤ 5,
–13 ≤ k ≤ 13,
–21 ≤ l ≤ 21
10209 / 3262
3016
0.45×0.29×0.26
3.1 ÷ 36.8
–13 ≤ h ≤ 18,
–11 ≤ k ≤ 12,
–19 ≤ l ≤ 17
11747 / 3996
3731
θmin÷θmax, deg
Limits of Miller indices
–16 ≤ h ≤ 16,
–
15 ≤ k ≤ 15,
–
23 ≤ l ≤ 23
Number of reflections: measured / independ.
used in refinement, I ≥ 2σ(I)
20777 / 10065
7650
Number of independent parameters
311
171
155
2
S on F
1.022
1.026
1.041
2 2
R[F > 2σ(F )]
0.0495
0.0510
0.0493
2
wR(F )
0.1288
0.1380
0.1361
3
Max / min of residual electron density, e/Å
0.94 / –0.77
1.25 / –0.64
1.37 / –1.09
environment of the third Cu3 atom, thus forming three fourth of the cube (–Cu Cl –). Interestingly that in nearly twenty
3 3
structurally studied complexes with the N,(C=C)-coordination of heteroatomic ligands to Cu(I) there are monomeric CuCl,
polymeric, or, more often, dimeric Cu Cl moieties, whereas the island Cu Cl moieties (Fig. 1) have not previously been
found [11, 21-23]. The distorted tetrahedral environment of Cu3 (τ = 0.79) in 1, in addition to three mentioned halogen
2
2
3
3
4
atoms, includes yet another olefinic C=C bond of one of the allyl groups of the second Bialtia molecule. The Cu3–Cl1
distance (2.977(1) Å) is much longer than the other Cu–Cl bonds in complex 1, but is shorter than the maximum contact
between Cu(I) and Cl (3.15 Å) in the structure of olefinic copper(I) π-complexes with allyl derivatives of heterocyclic
compounds [11].
Complex [Cu Cl (Bialtia)] (2) crystallizes in the orthorhombic crystal symmetry, in the acentric group P2 2 2 ; the
3 3 1 1 1
asymmetric unit of the structure contains three independent copper and chlorine atoms and only one organic ligand molecule
Fig. 2, Table 3). The coordination of the Bialtia molecule in 2, which is similar to that of the chelate-bridging π,σ-ligand in
, occurs via two N atoms of the heterocycle and two C=C bonds of the allyl groups. The Cu1 (τ = 0.88) and Cu2 (τ = 0.86)
atoms in complex 2 have a distorted tetrahedral environment. The absence of the olefinic bond π-coordinated to the Cu3 atom
(
1
4
4
s
390

Fig. 1. Asymmetric unit of the structure of [Cu Cl (Bialtia) ] complex (1). Disordered allyl
3 3 2
group is depicted by dashed lines.
TABLE 2. Main Bond Lengths and Bond Angles in the Structure of Complex 1
Bond
d, Å
Bond
d, Å
Angle
ω, deg
Angle
ω, deg
Cu1A–N13
Cu1A–Cl1
Cu1A–Cl2
Cu1A–m1
Cu2–N14
Cu2–Cl1
2.002(3)
2.289(2)
2.598(2)
1.944(3)
2.023(2)
2.323(1)
Cu2–Cl3
Cu2–m2
Cu3–Cl2
Cu3–Cl3
Cu3–m3
Cu3–Cl1
2.526(1)
1.966(3)
2.268(1)
2.265(1)
1.947(3)
2.977(1)
N13–Cu1А–m1
Cl1–Cu1А–m1
Cl2–Cu1А–m1
Cl1–Cu1А–Cl2
N14–Cu2–m2
Cl1–Cu2–m2
112.6(1)
132.3(1)
105.3(1)
98.12(8)
114.95(9)
131.88(9)
Cl3–Cu2–m2
Cl1–Cu2–Cl3
Cl1–Cu3–m3
Cl2–Cu3–m3
Cl3–Cu3–m3
Cu1A–Cl1–Cu2
100.19(9)
96.31(4)
105.63(8)
123.05(8)
126.01(8)
92.68(7)
Note. m1, m2, and m3 are the middles of the C11=C12А, C16=C17, and C21=C22 bonds respectively.
i
τ = 0.82) leads to the polymeric association of individual {Cu Cl } moieties through the appeared Cu3–Cl1 contact of
(
4
3
3
i
2.287(3) Å ( –0.5+x, 1.5–y, 1–z) in an infinite chain {[Cu
3 3 n
Cl (Bialtia)]} (Fig. 3a).
The structure of [Cu Cl (Bialtia)] complex (3) differs in the environment of two π-coordinated Cu1 and Cu2 atoms
2 2
(
Fig. 2b). The tetrahedral environment of the Cu1 atom includes the nitrogen atom of the 1,3,4-thiadiazole core, the C=C
bond of the allyl group, and two halogen atoms; the bridging Cl1 atom joins the Cu(I) atoms in a five-membered {N Cu Cl}
ring, whereas the Cl2 atom is purely terminal. Unlike 3, in the [Cu Cl (C H N )] π complex with allylacetone azine, where
2
2
2
2
12 20
2
2 2
the identical metal inorganic core with a five-membered {N Cu Cl} ring forms, the Cl2 atoms join individual links into
a polymer chain (Fig. 3b) [24]. The trigonal environment of the Cu2 atom in 3 consists of only the C=C bond, the N atom of
the heterocycle, and the mentioned bridging Cl1 atom because the nearest Cu2–Cl2 distance (3.922(2) Å) substantially
exceeds the sum of the van der Waals radii of the respective atoms. The tendency of the π-coordinated copper(І) atom to
bond to the terminal chlorine atom has previously been noted in the structures of CuCl compounds with 2-allylamino-5-
phenyl-1,3,4-thiadizole [7], 3-allyl-2-iminobenzothiazole [25], 1-allyl-3-methylpiperazine [26], and 3-allylthio-4-allyl-5-
phenyl-4H-1,2,4-triazole [27].
In the structures of 1-3 the hydrogen atoms of the allyl group are involved in the formation of a branched network of
C–H….X hydrogen contacts (X = Cl, S, N) (Table 4). To visualize the geometry of these bonds for the fragment of the
structure of 3, the Hirshfeld surface was analyzed and the respective fingerprint diagrams with the selected H…Cl and H…S
391

Fig. 2. Fragment of [Cu Cl (Bialtia)] structure (2) (a) and the asymmetric unit of [Cu Cl (Bialtia)] structure (3)
3 3 2 2
(
i
b). For clarity, the disordered part of the allyl group at the Cu2 atom is omitted in 2. Symmetry codes:
ii
0.5+x, 1.5–y, 1–z; 0.5+x, 1.5–y, 1–z.
–
TABLE 3. Main Bond Lengths and Bond Angles in the Structures of Complexes 2 and 3
Compound
Bond
2
3
Compound
Angle
2
3
d, Å
ω, deg
Cu1–N13
Cu1–Cl1
Cu1–Cl2
Cu1–m1
Cu2–N14
Cu2–Cl1
Cu2–Cl3
Cu2–m2
Cu3–Cl1
Cu3–Cl2
Cu3–Cl3
2.027(8)
2.429(3)
2.348(3)
2.040(9)
2.033(7)
2.370(3)
2.383(3)
1.976(9)
2.287(3)
2.255(3)
2.234(3)
2.287(3)
2.105(6)
2.384(2)
2.352(2)
1.995(6)
1.975(6)
2.224(2)
N13–Cu1–m1
Cl1–Cu1–m1
Cl2–Cu1–m1
Cl1–Cu1–Cl2
N14–Cu2–m2
Cl1–Cu2–m2
Cl3–Cu2–m2
Cl2–Cu2–Cl3
Cu1–Cl1–Cu2
Cl1–Cu3–Cl2
Cl1–Cu3–Cl3
111.8(4)
118.9(4)
108.2(4)
101.93(9)
111.0(6)
123.5(6)
115.6(6)
101.32(9)
90.49(8)
114.9(1)
125.4(1)
101.9(1)
109.4(3)
122.9(3)
119.4(3)
103.07(6)
117.0(3)
137.4(3)
1.909(6)
89.80(6)
i
i
Cu3–Cl1
Cl1–Cu3–Cl1
Note. m1 and m2 are the middles of the C11=C12 and C16=C17 (C16А=C17А in the structure of 2) bonds
i
respectively. Symmetry code: –0.5+x, 1.5–y, 1–z.
contacts were presented (Fig. 4). The contribution of the H...H contact to the surface is 19.9%. The Hirshfeld surface and the
corresponding fingerprint diagrams of the contacts were constructed using the CrystalExplorer software [28].
Thus, the formation of π-complexes 1-3, in particular, their inorganic constituents, is due to the participation of two
spatially directed allyl groups of the Bialtia molecule in the coordination of the metal atom. The coordination behavior of the
Bialtia ligand with four centers active with respect to copper(І) substantially differs from that in the previously studied
compounds with 2-allylamino-5-methyl-1,3,4-thiadiazole and 5-allylthio-1,3,4-thiadiazole-2-amine [6-9] prone to form solely
2+
2 2
dimeric {Cu L } moieties regardless of the nature of the inorganic anion.
392

Fig. 3. Inorganic polymer in the structure of 2 (a) and in the
structure of the [Cu Cl (C H N )] complex [24] with
2
2
12 20
2
π
allylacetone azine (b).
TABLE 4. Geometry of Selected Hydrogen Bonds in the Structures of 1, 2, and 3
Bond
Symmetry code
Distance, Å
Angle, deg
D–H⋯A
D⋯H
H⋯A
D⋯A
D–H⋯A
1
C13А–H13B⋯Cl3
C13B–H13C⋯Cl3
C12А–H12A⋯N24
C27–H27⋯S22
x, 1+y, z
x, 1+y, z
0.99
0.99
0.95
0.95
2.85
2.77
2.38
2.88
3.607(3)
3.560(9)
3.327(4)
3.711(4)
134
137
173
147
–1+x, 1+y, z
2–x, –y, 1–z
2
C13–H13B⋯Cl2
C18B–H18B⋯Cl2
C12–H12⋯S12
0.5+x, 0.5–y, 1–z
1–x, 0.5+y, 1.5–z
–0.5+x, 0.5–y, 1–z
0.99
0.99
0.95
2.84
2.63
2.90
3.46(1)
3.48(5)
3.72(1)
122
144
145
3
C13–H13B⋯Cl2
C12–H12⋯S13
–0.5+x, 1–y, z
0.99
0.95
2.85
2.96
3.524(7)
3.827(7)
126
153
1–x, 1–y, –0.5+z
Fig. 4. Hirshfeld surface (mapped with dnorm) for the fragment of the structure of 3 (a). The fingerprint
diagrams with the selected contacts H…Cl (b) and H…S (b, c).
393

REFERENCES
1
2
3
4
5
6
7
8
9
. Y. Hu, C.-Y. Li, X.-M. Wang, Y.-H. Zang, and H.-L. Zhu. Chem. Rev., 2014, 11, 5572.
. A. K. Jain, S. Sharma, A. Vaidya, V. Ravichandran, and R. K. Agrawal. Chem. Biol. Drug. Des., 2013, 8, 557.
. J. Matysiak. Mini Rev. Med. Chem., 2015, 15(9), 762.
. L. M. T. Frija, A. J. L. Pombeiro, and M. N. Kopylovich. Coord. Chem. Rev., 2016, 30, 32.
. G. Pulvermacher. Chem. Ber., 1894, 27(1), 613.
. B. Ardan, Yu. Slyvka, E. Goreshnik, and M. Mys′kiv. Acta. Chim. Slov., 2013, 6, 484.
. Yu. I. Slyvka, J. Struct. Chem, 2015, 56(6), 1118-1123.
. E. A. Goreshnik, G. Veryasov, D. Morozov, Yu. Slyvka, B. Ardan, and M. G. Mys′kiv. J. Organomet. Chem., 2016, 81, 1.
. B. Ardan, V. Kinzhybalo, Yu. Slyvka, O. Shyyka, M. Luk′yanov, T. Lis, and M. Mys′kiv. Acta Crystallogr., Sect. C,
2017, C7, 36.
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
0. R. G. Pearson. J. Am. Chem. Soc., 1963, 85(22), 3533.
1. Y. Slyvka, E. Goreshnik, O. Pavlyuk, and M. Mys′kiv. Cent. Eur. J. Chem., 2013, 1, 1875.
2. E. A. Goreshnik, Yu. I. Slyvka, and M. G. Mys'kiv. Inorg. Chim. Acta, 2011, 37, 177.
3. E. A. Goreshnik, A. A. Vakulka, Yu. I. Slyvka, and M. G. Mys'kiv. J. Organomet. Chem., 2012, 71, 1.
4. M. Bush. Chem. Ber., 1894, 2, 2507.
5. B. M. Mykhalichko and M. G. Mys′kiv, Ukranian Patent No. UA 25450 A. Bull., 1998 (6).
6. G. M. Sheldrick. Acta Crystallogr. Sect. A, 2015, A7, 3.
7. G. M. Sheldrick. Acta Crystallogr. Sect. C, 2015, C7, 3.
8. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, and H. Puschmann. J. Appl. Crystallogr., 2009, 4, 339.
9. L. Yang, D. R. Powell, and R. P. Houser. Dalton Trans., 2000, 955.
0. Yu. Slyvka, E. Goreshnik, N. Pokhodylo, O. Pavlyuk, and M. Mys′kiv. Acta Chim. Slovaca, 2016, 63(2), 399.
1. T. Duzak, B. Zarychta, and V. Olijnyk. Z. Anorg. Allg. Chem., 2014, 640(1), 57.
2. Z.-R. Qu, Z.-F. Chen, J. Zhang, R.-G. Xiong, B. F. Abrahams, and Z.-L. Xue. Organometallics, 2003, 22(14), 2814.
3. Yu.-M. Song, J. Pang, and K. Qian. J. Mol. Struct., 2006, 79, 210.
4. Ya. E. Filinchuk and M. G. Mys′kiv, Koord. Khim., 1998, 24(11), 845.
5. E. A. Goreshnik and M. G. Mys'kiv. Z. Anorg. Allg. Chem., 2007, 633(10), 1723.
6. J. Pang, G.-X. Wang, and R.-G. Xiong. Chin. J. Inorg. Chem., 2007, 23(7), 1227.
7. O. R. Hordiychuk, V. V. Kinzhybalo, E. A. Goreshnik, Y. I. Slyvka, M. S. Krawczyk, and M. G. Mys′kiv.
J. Organomet. Chem., 2017, 838, P. 1.
28. M. A. Spackman and D. Jayatilaka. CrystEngComm., 2009, 1, 19.
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