Copper(I) halide complexes with ethylenediaminium L0(H +)2, N,N,N',N'-tetraallylethylenediaminium L 4(H+)2, and N,N,N,N',N'- pentaallylethylenediaminium l5(H+).

Article abstract of DOI:10.1134/S1070328410030061

Alkylation of ethylenediamine with allyl bromide in the presence of NaHCO₃ in benzene-ethanol and acetone-ethanol gave N,N,N',N'-tetraallylethylenediamine L⁴ and N,N,N,N',N'- pentaallylethylenediaminium bromide (L⁵(H⁺)Br ₂), respectively. The ac electrochemical synthesis at copper wire electrodes in solutions of copper(II) halide and an appropriate ligand yielded single crystals of Cu(I) complexes with ethylenediaminium ([L⁰(H ⁺)₂]_0.5CuCl₂ (I) and [L ⁰(H⁺)₂]_0.5CuBr_1.67Cl _0.33 (II)) and its N-allyl derivatives N,N,N',N'- tetraallylethylenediaminium ([{L⁴(H⁺)₂} _0.5Cu₂Cl₃] (III)) and N,N,N,N',N'- pentaallylethylenediaminium ([L⁵(H⁺)Cu₄Br ₆] (IV)). The crystal structures of complexes I-IV were determined by X-ray diffraction. The isostructural crystals of complexes I and II are triclinic, space group P1, Z = 2. For I: a = 5.936(3), b = 6.387(3), c = 7.126(4) A, α = 67.82(4)°, β = 72.98(4)°, γ = 67.55(4)°, V = 227.7(2) A³. For II a = 6.110(3), b = 6.657(3), c = 7.309(3) A, α = 68.40(3)°, β = 72.38(3)°, γ = 67.23(3)°, V = 250.4(2) A³. In structures I and II, the organic cations are between infinite anionic chains (CuX ^-₂)_n. The crystals of π-complex III are triclinic, space group P1, a = 6.851(4), b = 8.729(4), c = 9.960(4) A, α = 98.25(3)°, β = 102.29(3)°, γ = 107.30(3)°, V = 541.8(5) A³, Z = 2. In structure III, all the four allyl groups are π-coordinated by the metal atoms of four discrete anions Cu₄Cl^2-₆. The crystals of π-complex IV are monoclinic, space group C2/c, a = 15.228(5), b = 17.095(6), c = 20.182(6) A, β = 92.43(4)°, V = 5249(3) A³, Z = 8. Only two of five allyl groups at the same N atom are coordinated by copper(I) atoms. Structure IV contains a complex inorganic fragment of the formula (Cu ₄Br^2-₆)_n.

Full text of DOI:10.1134/S1070328410030061

ISSN 1070ꢀ3284, Russian Journal of Coordination Chemistry, 2010, Vol. 36, No. 3, pp. 198–203. © Pleiades Publishing, Ltd., 2010.
Original Russian Text © M.M. Monchak, A.V. Pavlyuk, V.V. Kinzhibalo, V.V. Glukhyi, M.G. Mys’kiv, 2010, published in Koordinatsionnaya Khimiya, 2010, Vol. 36, No. 3,
pp. 200–205.
Copper(I) Halide Complexes with Ethylenediaminium L0(H+)2,
N,N,N',N'ꢀTetraallylethylenediaminium L4(H+)2,
and N,N,N,N',N'ꢀPentaallylethylenediaminium L5(H+).
Synthesis and Crystal Structures of the Complexes
[L0(H+)2]0.5CuCl2, [L0(H+)2]0.5CuBr1.67Cl0.33, [{L4(H+)2}0.5Cu2Cl3],
and [L5(H+)Cu4Br6]
M. M. Monchaka, A. V. Pavlyuka, b, V. V. Kinzhibalob, V. V. Glukhyic, and M. G. Mys’kiva, *
a Franko National University, ul. Kirila i Mefodiya 6, Lviv, 290005 Ukraine
b Wroclaw University, Wroclaw, Poland
c Technological University, Munich, Germany
*Eꢀmail: myskiv@franko.lviv.ua
Received July 14, 2009
Abstract—Alkylation of ethylenediamine with allyl bromide in the presence of NaHCO3 in benzene–ethaꢀ
nol and acetone–ethanol gave N,N,N',N'ꢀtetraallylethylenediamine L4 and N,N,N,N',N'ꢀpentaallylethylꢀ
enediaminium bromide (L5(H+)Br2), respectively. The ac electrochemical synthesis at copper wire electrodes
in solutions of copper(II) halide and an appropriate ligand yielded single crystals of Cu(I) complexes with
ethylenediaminium ([L0(H+)2]0.5CuCl2 (
I)
and [L0(H+)2]0.5CuBr1.67Cl0.33
(
II)) and its Nꢀallyl derivatives
N,N,N',N'ꢀtetraallylethylenediaminium ([{L4(H+)2}0.5Cu2Cl3] (III)) and N,N,N,N',N'ꢀpentaallylethyleneꢀ
diaminium ([L5(H+)Cu4Br6] (IV)). The crystal structures of complexes
IV were determined by Xꢀray difꢀ
fraction. The isostructural crystals of complexes and II are triclinic, space group = 2. For
= 67.82(4) = 72.98(4) = 67.55(4)
= 227.7(2) Å3. For II
= 68.40(3) = 72.38(3) = 67.23(3)
= 250.4(2) Å3. In strucꢀ
n. The crystals of ꢀcomplex III
= 98.25(3) = 102.29(3)
= 2. In structure III, all the four allyl groups are ꢀcoordinated by the metal
atoms of four discrete anions Cu4Cl62–
The crystals of ꢀcomplex IV are monoclinic, space group 2/
= 15.228(5), = 17.095(6), = 20.182(6) = 92.43(4) = 8. Only two of five allyl groups
= 5249(3) Å3
at the same N atom are coordinated by copper(I) atoms. Structure IV contains a complex inorganic fragment
of the formula (Cu4Br62–
I–
I
P
1
,
Z
I:
a
a
= 5.936(3),
= 6.110(3),
b
= 6.387(3),
c
= 7.126(4)
Å
,
α
°
,
β
°
,
γ
°
, V
b
= 6.657(3),
c
= 7.309(3)
Å
,
α
°,
β
°,
γ
°
, V
tures
are triclinic, space group
= 107.30(3)
= 541.8(5) Å3
I
and II, the organic cations are between infinite anionic chains (CuX2–
)
π
P
1
,
a
= 6.851(4), = 8.729(4), = 9.960(4)
b
c
Å
,
α
°,
β
°,
γ
°
,
V
,
Z
π
.
π
C c,
a
b
c
Å,
β
°,
V
, Z
)
.
n
DOI: 10.1134/S1070328410030061
Although copper complexes with molecular ethylꢀ plexes with its cationic allyl derivatives N,N,N',N'ꢀ
tetraallylethylenediaminium
[{L4(H+)2}0.5Cu2Cl3] (III and N,N,N,N',N'ꢀpentaalꢀ
lylethylenediaminium L5(H+) – [L5(H+)Cu4Br6] (IV
(
L4(H+)2)
–
enediamine (En) have long been known [1], cuprous
complexes with its cationic form, as well as with Nꢀ
allyl derivatives of En, have not been studied.
).
Here we presented the results of our study.
Recently,
N,N,N,N',N',N'ꢀhexaallylethylenediaminium (L6) of
the formulas [L6(Cu4Br4.55Cl1.45)] and [L6(Cu4Br6)
π
ꢀcomplexes of copper(I) halides with
]
EXPERIMENTAL
were obtained and examined by Xꢀray diffraction [2].
Proceeding further in these investigations, we preꢀ
pared single crystals of copper complexes with ethylꢀ
Synthesis. N,N,N',N'ꢀTetraallylethylenediamine
L4) was prepared from predried and freshly distilled
(
enediaminium
(
[L0(H+)2]0.5CuCl2
II ) and copper(I)
(
I
)
and
ethylenediamine and allyl bromide in a molar ratio of
[L0(H+)2]0.5CuBr1.67Cl0.33
(
)
π
ꢀcomꢀ 1 : 2 in the presence of NaHCO3. The reaction mixture
198

COPPER(I) HALIDE COMPLEXES
199
was refluxed with vigorous stirring in benzene–ethaꢀ
nol for 36 h. The precipitate (a mixture of En 2HBr,
·
NaBr, and the residual NaHCO3) was filtered off and
the filtrate was concentrated. The resulting concenꢀ
trate of the ligand was used in the synthesis of
complex III
.
H(1N)
H(1B)
N,N,N,N',N'ꢀPentaallylethylenediaminium broꢀ
mide (L5H+)Br2 was prepared from ethylenediamine
and allyl bromide in a molar ratio of 1 : 5 in the presꢀ
ence of NaHCO3. The reaction mixture was refluxed
with vigorous stirring in acetone–ethanol for 48 h.
The precipitate of NaBr was filtered off and the filtrate
was concentrated. The resulting concentrate of
H(3N)
N(1)
C(1)
H(2N)
Cu
y
X(2)
X(1)
(L5H+)Br2 was used in the synthesis of complex IV
.
x
z
Colorless crystals of complexes and II were
I
obtained by ac electrochemical synthesis [3] at copper
wire electrodes in an aqueous methanol solution of
Fig. 1. Fragment of structures
2.329(1) Å; Cu–Cl(2), 2.340(1) Å; Cu–Cl(1), 2.392(1) Å;
Cu–Cl(2)ii, 2.414(1) Å; Cu–X(1)ii, 2.448(1) Å; Cu–X(1),
2.507(1) Å; Cu–X(2)ii, 2.443(1) Å; Cu–X(2), 2.470(1) Å.
The symmetry operation codes are (i) –x, 1 – y, 1 – z and
I and II: Cu–Cl(1)ii,
CuCl2
(
⋅
2H2O and ethylenediamine titrated with HCl
I) or HBr (II) to pH 4 for a day.
(ii) 1 – x, 1 – y, 1 – z.
Yellowish crystals of πꢀcomplex III were grown on
copper wire electrodes from an ethanolic solution of
CuCl2 ⋅
crystals of complex II grew on a copper wire even
under electroless conditions.
2H2O and L4(H+)2Cl2 in two days. Smaller
RESULTS AND DISCUSSION
Structures
I
and II contain an infinite cuprous
composed of the
halide inorganic fragment (CuX2–
)
n
Red crystals of complex IV were obtained by ac
electrochemical synthesis on copper wire electrodes in
an ethanolic solution of CuBr2 and (L5H+)Br2 for 17 h.
tetrahedra СuХ4 with their opposite edges in common
(Fig. 1). Such an inorganic fragment was found in the
complexes [CuII(En)2][Cu2Cl4] [7], [Nꢀallylquinolinꢀ
Xꢀray diffraction analysis. Structures
examined first by the photometric method and then by
Xꢀray diffraction. Reflection intensities were collected [9]. The ethylenediaminium cations in structures
I–IV were
ium]CuBr2 [8], and [Cu(OOCH)(C3H5NH3)CuBr2
]
I
and II are between separate cuprous halide chains,
being nearly perpendicular to them, and are not coorꢀ
dinated by copper(I) atoms because of the presence of
on KUMAꢀKM4/CCD and Xcalibur XPS singleꢀ
crystal diffractometers (CCD detector, Mo radiaꢀ
K
α
tion, graphite monochromator,
ω
scan mode, an
the protonated N atoms. Structures
lized by a branched system of the hydrogen bonds
(N)H⋅⋅⋅ and (С)H⋅⋅⋅
I and II are stabiꢀ
OXFORD Cryosystem lowꢀtemperature attachment)
and corrected for the Lorentz and polarization factors.
The data obtained were processed with the CrysAlis
X
X.
RED program [4]. Structures I–IV were solved by
Since the C=C bonds of all the four allyl groups in
L4(H+)2Cl2 are coordinated by four metal atoms
direct methods. Light atoms were located from differꢀ
ence electronꢀdensity maps. An absorption correction
was applied by the analytical method [5]. All calculaꢀ
tions were performed with the SHELX program packꢀ
(Fig. 2), ꢀcomplex III contains an islet inorganic
π
fragment Cu4Cl6 with two independent copper(I)
atoms. The cation L4(H+)2 acts as a bridge between
age [6]. The hydrogen atoms in complex I were located
from difference electronꢀdensity maps and refined in four Cu4C l26– anions. Thus, structure III consists of
the riding model together with nonꢀhydrogen atoms.
In complexes II IV, almost all positions of the hydroꢀ
gen atoms were calculated geometrically. Crystalloꢀ
graphic parameters and the data collection statistics
layers formed by the N,N,N',N'ꢀtetraallylethylenediꢀ
–
aminium cations and the Cu4C l26– anions joined
together. The coordination polyhedra of the Cu(1)
and Cu(2) atoms are trigonal pyramids made up of two
Cl atoms and the double bond in the equatorial plane
and an apical Cl atom. The lengths of the coordinated
C(3)=C(4) and C(6)=C(7) bonds are 1.37(1) and
1.36(1) Å, respectively.
for structures
I–IV are summarized in Table 1.
Selected bond lengths and bond angles are given in the
figure captions.
The atomic coordinates and other parameters of
complexes I–IV have been deposited with the Camꢀ
bridge Crystallographic Data Collection (nos. 738584,
738585, 738586, and 738587, respectively; http://
www.ccdc.ac.uk/conts/retrieving.html).
Structure IV is organized in an absolutely different
way: the rather complex polymeric anion (Cu4Br62–
)
n
contains four crystallographically independent copꢀ
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 36
No. 3
2010

200
MONCHAK et al.
Table 1. Crystallographic parameters and the data collection statistics for structures I–IV
Value
Parameter
I
II
III
IV
Empirical formula
M
CH5NCuCl2
165.51
CH5NCuBr1.67Cl0.33
238.9
C7H13NCu2Cl3
344.54
C17H30N2Cu4Br6
995.8
Crystal size, mm
Temperature, K
Crystal color and shape
0.15
×
0.10
110
×
0.06
0.11
×
0.13
150
×
0.08
0.37
×
0.22
100
×
0.14
0.33
×
0.26
240
×
0.12
Colorless prisms
Colorless prisms
Yellowish prisms
Red prisms
2/
Space group
C c
P
1
P
1
P1
Unit cell parameters
:
a
, Å
, Å
5.936(3)
6.387(3)
7.126(4)
67.82(4)
72.98(4)
67.55(4)
227.7(2)
2
6.110(3)
6.657(3)
7.309(3)
68.40(3)
72.38(3)
67.23(3)
250.4(2)
2
6.851(4)
8.729(4)
9.960(4)
98.25(3)
102.29(3)
107.30(3)
541.8(5)
2
15.228(5)
17.095(6)
20.182(6)
90
b
c
, Å
, deg
, deg
, deg
α
β
92.43(4)
90
γ
V
Z
, Å3
5249(3)
8
ρcalcd, g/cm3
ρexp, g/cm3
2.414
3.176
2.112
2.521
2.42
2.37
2.05
μ
, mm–1
5.77
17.64
221.4
4.62
12.34
3776
F(000)
162
342
Ranges of h, k, and l indiꢀ
ces
–8 <
–11 <
–12 <
h
k
l
< 11
< 11
< 13
–7 <
–9 <
–10 <
h
< 9
–7 <
–11 <
–13 <
h
k
l
< 11
< 14
< 13
–18 <
–20 <
–22 <
h
k
l
< 17
< 19
< 24
k
< 10
< 10
l
Rint
0.023
4810
0.021
4283
0.034
5903
0.093
23414
Number of measured reꢀ
flections
Number of reflections
1661
66
1467
49
2676
122
3677
250
with
F
> 4σ(F)
Number of parameters reꢀ
fined
2θmax, deg
84
65.1
73.6
50.1
2
2
2
2
2
2
2
2
[
σ (Fo)
+
[
σ (Fo)
+
[
σ (Fo) +(0.0445P P
)2 + [σ (Fo) + (0.0336 )2 +
Weighting scheme
*
–1
–1
(0.015
P
)2]–1
(0.0507
P
)2]–1
0.3295P]
118.4823P]
R
(
F2)(
wR
GOOF
Δρmax Δρmin
F
> 4
σ
(
F
))
0.029
0.044
0.027
0.072
0.030
0.077
0.069
0.131
1.14
0.95
1.07
1.06
/
,
e
Å–3
0.56/–0.88
1.12/–0.89
1.05/–0.47
1.58/–0.85
* P = (F2o + 2F2c) /3.
per(I) atoms, two of which ꢀcoordinate the allyl C=C bromide chains (Fig. 5). A comparison of structure IV
π
with the structure of the
ꢀcomplex [L6(Cu4Br6)] studꢀ
π
bonds at the same N atom of the ligand (Fig. 3), while
the coordination polyhedra of two other Cu(I) atoms
consist of the Br atoms only (Fig. 4). The cation
L5(H+) bridges metal atoms from two different cuprous
ied in [2] revealed a striking difference in the behavior
of the bridging acentric and centrosymmetric polyalꢀ
lylethylenediaminium cations ([L5(H+)]2+ and (L6)2+
,
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 36
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2010

COPPER(I) HALIDE COMPLEXES
201
y
x
z
C(4)
C(3)
N(1)
C(2)
C(7)
C(6)
Cl(3)
C(1)
H
C(5)
Cu(2)
Cu(1)
Cl(2)
Cl(1)
Fig. 2. Unique bridging function of N,N,N',N'ꢀtetraallylethylenediaminium in structure III: Cu(1)–Cl(1), 2.273(1) Å; Cu(1)–
Cl(2), 2.573(2) Å; Cu(1)–Cl(3), 2.310(1) Å; C(3)=C(4), 1.37(1) Å; Cu(1)– (3,4)*, 1.973(1) Å; C(4)Cu(1)C(3), 38.30(9)°;
Cu(2)–Cl(2), 2.253(1) Å; Cu(2)–Cl(3)i, 2.309(1) Å; C(6)=C(7), 1.36(1) Å; Cu(2)–
(6,7)** 1.949(1) Å; C(7)Cu(2)C(6),
m
m
38.41(10)° (*
operation code is (i) –
m
(3,4) is the midpoint of the C(3)=C(4) bond; **
m(6,7) is the midpoint of the C(6)=C(7) bond). The symmetry
x
, – , –
y
z.
y
x
Cu(2)
C(8)
z
C(11)
C(5)
C(6)
C(7)
C(10)
C(9)
N(1)
Cu(1)
C(3)
C(4) C(1)
C(2)
N(2)
C(13)
C(14)
C(15)
C(16)
C(12)
C(17)
Fig. 3. πꢀCoordinated N,N,N,N',N'ꢀpentaallylethylenediaminium cation in structure IV: C(4)=C(5), 1.36(1) Å; Cu(1)–C(4),
2.120(10) Å; Cu(1)–C(5), 2.160(9) Å; C(4)Cu(1)C(5), 37.0(4)°; C(10)=C(11), 1.36(1) Å; Cu(2)–C(10), 2.135(10) Å; Cu(2)–
C(11), 2.121(10) Å; C(11)Cu(2)C(10), 37.3(4)°.
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 36
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202
MONCHAK et al.
z
x
y
Br(6)
Br
Cu
Cu(3)
C
Br(1)
H
Br(5)
Br(2)
Br(4)
N
Cu(4)
Br(7)
Cu(2)
Cu(1)
y
x
z
C
H
Br(3)
Br(8)
Fig. 4. Fragment of the polymeric anion (Cu Br62–
) in
n
4
Fig. 5. Fragment of structure IV
.
structure IV: Cu(1)–
2.443(2) Å; Cu(1)–Br(2), 2.432(2) Å; Cu(1)–Br(3),
2.645(2) Å; Cu(2)– (10,11)**, 2.016(1) Å; Cu(2)–Br(2),
2.418(2) Å; Cu(2)–Br(4), 2.855(2) Å; Cu(2)–Br(5)i,
2.424(2) Å (* (4,5) is the midpoint of the C(4)=C(5)
bond; ** (10,11) is the midpoint of the C(10)=C(11)
bond). The other Cu–Br bond lengths range from 2.351(2)
to 2.538(2) Å. The symmetry operation code is (i) –
+ 3/2.
m(4,5)*, 2.029(1) Å; Cu(1)–Br(1),
m
Cu(3) atom. The coordination polygon of the Cu(4)
atom is a triangle composed of Br atoms. The coordiꢀ
nation polyhedra of the Cu(1), Cu(2), and Cu(3)
atoms are united through bromine atoms into sixꢀ
membered cuprous bromide rings in the chair conforꢀ
mation.
m
m
x, y,
–
z
respectively). The lengths of the coordinated
C(4)=C(5) and C(10)=C(11) bonds in structure IV
Structures
I–IV are additionally stabilized by
hydrogen bonds [10–12] (Table 2). They link the
organic and inorganic parts in ethylenediaminium
I and II and fix the uncoordinated allyl
groups in complex IV, thus preventing their too strong
are 1.36(1) Å
.
The coordination polyhedra of the ꢀ
π
coordinated Cu(1) and Cu(2) atoms are trigonal pyraꢀ
mids made up of the C=C bond in the pyramid base
and three Br atoms as the other vertices. Bromine
complexes
atoms form a tetrahedral environment around the sway.
Table 2. Geometrical parameters of the hydrogen bonds in structures I–IV
Distance, Å
Angles D–H⋅⋅⋅A,
Complex
Contact D–H⋅⋅⋅
A
Coordinates of atom A
1 – , 1 – , 1 – z
deg
D–H
H⋅⋅⋅A
D⋅⋅⋅A
I
N(1)–H(2N)⋅⋅⋅Cl(2)
N(1)–H(1N)⋅⋅⋅Cl(1)
N(1)–H(3N)⋅⋅⋅Cl(2)
C(1)–H(1B)⋅⋅⋅Cl(1)
N(1)–H(1N)⋅⋅⋅X(1)
N(1)–H(3N)⋅⋅⋅X(2)
N(1)–H(2N)⋅⋅⋅X(1)
0.87(2)
0.92(2)
0.84(2)
0.90(2)
0.91
2.40(3)
2.27(4)
2.63(6)
2.84(3)
2.51
3.27(4)
3.18(7)
3.28(6)
3.60(4)
3.39(4)
3.31(4)
3.38(3)
3.69(3)
3.07(1)
3.58(3)
3.47(4)
3.74(7)
3.87(2)
3.85(4)
173(2)
177(3)
135(2)
143(1)
165
x
y
x
x
, 1 +
y
,
z
z
,
y, 1 +
–
–
–
x
x
x
, 1 –
, 1 –
, 2 –
y, 1 –
y, 1 –
y, 1 –
z
z
z
II
0.91
2.42
167
0.91
2.63
140
x
,
y
, 1 +
–1 +
1 – , 1 –
z
C(1)–H(1B)⋅⋅⋅X(2)
0.99
2.90
138
x
,
y
,
z
III
IV
N(1)–H(1N)⋅⋅⋅Cl(1)
C(5)–H(5A)⋅⋅⋅Cl(2)
C(1)–H(1A)⋅⋅⋅Cl(1)
C(4)–H(4A)⋅⋅⋅Br(6)
C(5)–H(5B)⋅⋅⋅Br(5)
C(13)–H(13A)⋅⋅⋅Br(1)
0.90(3)
0.99
2.23(3)
2.63
157(3)
163
x
y
, 1 – z
–
–
x
x
, 1 –
, 1 –
y
, –
z
0.99
2.79
126
y, 1 –
z
0.94
2.83
163
0.5 –
0.5 –
x
x
, 0.5 +
, 0.5 +
y
y
, 1.5 –
, 1.5 –
z
z
0.94
2.96
162
0.94
2.96
160
x, y, z
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 36
No. 3
2010

COPPER(I) HALIDE COMPLEXES
203
3. RF Patent 25450, Byull. Izobret., 1998, no. 6.
To sum up, it should be noted that modification of
the
ethylenediaminium
cations
En(H+)2,
4. CrysAlis RED, Oxford: Diffraction Ltd., Version
1.171.31.8 (release 12ꢀ01ꢀ2007).
2+
6
En(C3H5)4(H+)2, En(C3H5)5(H+), and En(C3H5
)
5. Clark, R.C. and Reid, J.S., Acta Crystallogr. Sect. A:
Found. Crystallogr., 1995, vol. 51, no. 6, p. 887.
(
L0(H+)2, L4(H+)2, L5(H+), and (L6)2+, respectively)
with allyl groups [2] opens the route to various crystalꢀ
line Cu(I) complexes, thus extending the scope of
6. Sheldrick, G.M., SHELXSꢀ97 and SHELXLꢀ97. Proꢀ
gram for the Solution and Refinement of Crystal Strucꢀ
tures, Göttingen (Germany): Univ. of Göttingen, 1997.
crystalline design of copper(I) πꢀcomplexes [13].
7. Simonsen, O. and Hofthund, H., Acta Crystallogr.,
Sect. C: Cryst. Struct. Commun., 1987, vol. 43, no. 5,
p. 831.
ACKNOWLEDGMENTS
M.M. Monchak is grateful to the DAAD foundaꢀ
tion for supporting this study.
M.M. Monchak, A.V. Pavlyuk, and M.G. Mys’kiv
are grateful to the Ministry of Education and Science
of Ukraine for supporting this study (the Ukrainian–
Slovenian agreement on scientific and technical coopꢀ
eration, grant M/55ꢀ2009).
8. Pavlyuk, A.V., Davydov, V.N., and Mys’kiv, M.G.,
Koord. Khim., 2003, vol. 29, no. 3, p. 213 [Russ. J.
Coord. Chem. (Engl. Transl.), vol. 29, no. 3, p. 199].
9. Mykhalichko, B.M., Oliinik, V.V., Mys’kiv, M.G., and
Pecharskii, V.N., Koord. Khim., 1994, vol. 20, no. 3,
p. 208.
10. Braga, D. and Grepioni, F., Dalton Trans., 1999, no. 1,
p. 1.
11. Desiraju, G.R. and Steiner, T., Weak Hydrogen Bond in
Structural Chemistry and Biology, Oxford: Oxford
Univ., 1999.
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,
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2010