The Influence of Solvents on the Alkylation of Carboxylate Phosphabetaines with Alkyl Iodides

Article abstract of DOI:10.1134/S1070363217120064

The new alkylation reactions of a series of mono- and dicarboxylate phosphabetaines with methyl and ethyl iodides in different solvents have been studied. These reactions have afforded stable compounds: iodine-containing salts of phosphonium with different structure.

Full text of DOI:10.1134/S1070363217120064

ISSN 1070-3632, Russian Journal of General Chemistry, 2017, Vol. 87, No. 12, pp. 2789–2793. © Pleiades Publishing, Ltd., 2017.
Original Russian Text © Yu.V. Bakhtiyarova, R.R. Minnullin, D.I. Bakhtiyarov, M.V. Morozov, K.A. Ivshin, I.V. Galkina, O.N. Kataeva, V.I. Galkin, 2017,
published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 12, pp. 1971–1976.
Dedicated to B.I. Buzykin on His 80th Anniversary
The Influence of Solvents on the Alkylation
of Carboxylate Phosphabetaines with Alkyl Iodides
Yu. V. Bakhtiyarova, R. R. Minnullin, D. I. Bakhtiyarov, M. V. Morozov,
K. A. Ivshin, I. V. Galkina*, O. N. Kataeva, and V. I. Galkin
Kazan Federal University, ul. Kremlevskaya 18, Kazan, Tatarstan, 420008 Russia
*
e-mail: vig54@mail.ru
Received July 31, 2017
Abstract―The new alkylation reactions of a series of mono- and dicarboxylate phosphabetaines with methyl
and ethyl iodides in different solvents have been studied. These reactions have afforded stable compounds:
iodine-containing salts of phosphonium with different structure.
Keywords: iodine-containing phosphonium salts, dicarboxylate phosphabetaine, X-ray diffraction
DOI: 10.1134/S1070363217120064
We have earlier studied synthesis, structure, and
reactivity of monocaboxylate phosphabetaines and
their derivatives [1–8]. In particular, it has been shown
that structurally similar phosphabetaines with different
substituents at the phosphorus atom can be easily
alkylated with alkyl halides. Composition and structure
of the formed phosphonium salts have been confirmed
by elemental analysis, NMR and IR spectroscopy, and
X-ray diffraction data [2–5, 7].
formation of the corresponding phosphonium salt 2
(Scheme 1). The salt structure was confirmed by a set
of spectral methods and X-ray structure analysis.
Furthermore, we synthesized a number of dicarboxylate
phosphabetaines 3–9 based on 3-(diphenylphosphino)-
propanoic acid and unsaturated carboxylic acids
(Scheme 2), and the alkylation reactions of some of
them were studied [10–12].
It should be noted that the conditions of the alkyla-
tion of dicarboxylate phosphabetaines are slightly
different from the alkylation of monocarboxylate ones.
Herein we report the alkylation of phosphabetain 1
[
9] with ethyl iodide. The reaction proceeded with the
Scheme 1.
_
C H
C H
6
5
6
5
I
C H I, CH CN
_
2
5
3
+
+
C H
P
COO
C H
P
COOEt
6
5
6
5
C H
C H
6
5
6
5
1
2
Scheme 2.
2
C6H
5
C6H5
C H R
6
5
+
P
1
PCH CH COOH + R CH=CCOOH
2
2
_
C H
R2
OOC
COOH
6
5
R1
3_
9
1
1
2
1
2
1
2
1
2
2
1
R = R = H (3); R = CH
3
, R = H (4); R = H, R = CH
3
(5); R = C
6
H
5
, R = H (6); R = 3-ClC
6
H
4
, R = H (7); R =
2
1
2
2
-thienyl, R = H (8); R = 3,5-(t-C
4
H
9
)
2
-4-OH-C
6
H
4
, R = H (9).
2
789

2
790
BAKHTIYAROVA et al.
Scheme 3.
(
(
CH ) COO
(CH ) COOCH
3
2
2
2 2
CH I, CH CN
CH CN, t
3
3
3
(
C H ) P
(C H ) P
I
(C H ) PCH CH COOCH
6 5 2 2 2 3
6
5 2
6
5 2
_CO
2
CH ) COOH
(CH ) COOH
2
2
2 2
C H
I
2
5
3
10
11
Scheme 4.
C H C6H5
C H
C6H5 C H
6 5
6
5
C H
6
5
6
5
CH3I
HOOC CHCHP(CH) COO
H COOC CHCHP(CH) COOH + HOOC CHCHP(CH ) COOCH
2
3
2
2 2
3
2
1
R2
2
1
1
R R
I
R R
12 14
12a 14a
6 5
(5, 13, 13а); R = C H , R = H (6, 14, 14а).
I
R
4_
6
1
_
_
2
1
2
1
2
R = CH
3
, R = H (4, 12, 12а); R = H, R = CH
3
For example, it has been shown [10] that phosphonium
salt 10 is firstly formed during the alkylation of
symmetric (with respect to the phosphonium center)
dicarboxylate betaine 3 with methyl iodide in
acetonitrile medium (Scheme 3). Methyl iodide itself
has been used as the solvent, but dicarboxylate phos-
phabetaine is limitedly soluble in it. Further heating of
the reaction mixture in acetonitrile in order to increase
the solubility has led to decarboxylation with the
formation of compound 11 [10].
Further investigation of alkylation of dicarboxylate
phosphabetaines synthesized basing on 3-(diphenyl-
phosphino)propanoic acid revealed considerable in-
fluence of the solvent on the reaction pathway.
The limited solubility of phosphabetaine 3 in the
majority of solvents prompted us to add a small amount
of ethanol to the reaction mixture. That led to complete
dissolution of the phosphabetaine, and the reaction
31
mixture turned red. Р NMR spectrum of the obtained
phosphonium salt 16 contained a signal of quaternary
1
13
In the present study, we performed the reactions of
alkylation of the non-symmetric (with respect to the
phosphonium center) dicarboxylate phosphabetaines
derived from crotonic (4), methacrylic (5) and
cinnamic (6) acids. The reactions practically did not
occur at room temperature. In should be noted that
phosphabetaine 6 is insoluble in organic solvents and
water. However, in the case of heating of the reaction
mixtures during 5 h (70°С), alkylation reaction
occurred with the formation of monoalkylation pro-
ducts 12–14 and 12а–14а (Scheme 4).
phosphorous atom at 28 ppm. According to Н and С
NMR spectroscopy data, the alkylation occurred simul-
taneously involving both carboxylic and carboxylate
groups (Scheme 5). Moreover, the ester group
contained the ethyl substituent, but not the methyl one.
The same phosphonium salt 16 is formed via alkyla-
tion of tricarboxylate phosphabetaine 15 obtained based
on 3-(diphenylphosphino)propanoic and maleic acids,
in the presence of ethanol [10]. The reaction occurs at
4
0°С with decarboxylation. The phosphonium salt 16
was a crystalline substance melting at 139°С; its
3
1
1
13
31
Р NMR spectra of the reaction mixtures contained
structure was confirmed by IR, Н, С, and Р NMR
two close signals of phosphorous nuclei, suggesting
the formation of isomers. The ratio of the integral
intensities of the isomers’ signals was close to 1 : 1. At
the same time, the С NMR signals were doubled,
further confirming the isomers formation.
spectroscopy, and X-ray diffraction data (Fig. 1).
To confirm the general character of alkylation of di-
carboxylate phosphabetaines, we carried out those reac-
tions in the presence of different alcohols (methanol,
ethanol, and isopropanol). Hence, the initial reaction
mixtures contained the dicarboxylate phosphabetaine
3, methyl iodide (excess) and a monohydric alcohol.
Using the mentioned alcohol, the corresponding phos-
phonium salts were isolated as products 16–18
(Scheme 6). In the presence of water, the reactions
occurred differently. For example, alkylation of
betaine 3 with methyl iodide was studied (Scheme 7).
1
3
The formation of such isomers in equal ratio
evidenced the absence of explicit carboxylic and car-
boxylate groups in the initial dicarboxylate phospha-
betaines, a proton equally belonging to both groups
[
11]. If a proton was localized at one of the carboxylic
groups, a single isomer would be formed in the alkyla-
tion reaction.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 12 2017

THE INFLUENCE OF SOLVENTS ON THE ALKYLATION
2791
Fig. 1. Molecular structure of (4-ethoxy-4-oxobutyl)tri-
Fig. 2. The molecular structure of bis(3-ethoxy-3-oxo-
phenylphosphonium iodide 2.
propyl)diphenylphosphnium iodide 16.
The structure of obtained compounds was confirmed
by IR and NMR spectroscopy as well as X-ray
diffraction analysis data (Fig. 2). It is obvious that in
the latter case the elimination of acrylic acid molecule
from initial dicarboxylate betaine occurred, followed
by the alkylation at the trivalent phosphorous atom
with methyl iodide.
stituent in the product was a part of the alcohol
molecule rather than the alkyl halide fragment.
EXPERIMENTAL
1
13
H and С NMR spectra were recorded using a
Bruker Avance-400 spectrometer. Chemical shifts
were determined relative to external references in D O.
2
In summary, we discovered an unusual and earlier
unknown way of alkylation of dicarboxylate phospha-
betaines in the presence of alcohols. The alkyl sub-
The IR spectra were recorded using an IR Prestige-21
spectrometer (400–3700 cm , suspension in Vaseline
oil or liquid film between KBr plates).
–
1
Scheme 5.
C H (CH ) COOC H
C H
(CH ) COO
C H
(CH ) COO
6
5
2 2
CH3I,
C H OH, t
6
5
2 2
2
5
6
5
2 2
C H OH, t
2
5
2 5
P
P
P
_
I
3
_
CH OH
CH OH,
3
3
_
CO2
C H
(CH ) COOH
C H (CH ) COOC H
C H
CHCH COOH
6
5
2 2
6
5
2 2
2
5
6
5
2
COOH
15
3
16
Scheme 6.
C H
(CH ) COO
C H
(CH ) COOR
2 2
6
5
2 2
6
5
ROH, t
P
+ CH3I
P
I3
(CH ) COOR
_
CH OH
3
C H
(CH ) COOH
C H
6
5
2 2
6
5
2 2
_
3
16 18
R = C
2
H
5
(16), CH
3
3 7
(17), i-C H (18).
Scheme 7.
C H
C H
6 5
6
5
i-C H OH, H O
3
7
2
C H
P
CH CH COO + CH3I
C H
P
CH CH COOH
I
6
5
2
2
6
5
2
2
_
CH =CHCOOH
2
CH CH COOH
CH
19
3
2
2
3
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 12 2017

2
792
BAKHTIYAROVA et al.
X-ray diffraction data were collected using a
Bruker AXS Kappa APEX Duo diffractometer with
Bis(3-ethoxy-3-oxopropyl)diphenylphosphnium
iodide (16). A solution of 2 g (14.1 mmol) of methyl
iodide in 15 mL of anhydrous ethanol was added to a
solution of 0.24 g (0.73 mmol) of 3-[(2-carboxyethyl)-
diphenylphosphyno]propanoate in 10 mL of the same
solvent. The reaction mixture was heated in a water
bath during 20 h. Needle-shaped red crystals were
filtered off, washed several times with diethyl ether on
MoK X-ray irradiation (λ 0.71073 Å) at 293(2) K and
α
processed using APEX2 [13], SAINT [14], SADABS
accounting for absorption) [15], and SHELXS97
solving the structure) [16] software. The structure was
refined by least squares method implemented in
SHELXL-2014 software package [17].
(
(
a porous glass filter and dried under vacuum. Yield
Crystals of compound 2 were rhombic, crystal
size 0.096×0.124×0.549 mm , M 504.32 g/mol,
–1
0
.29 g (63%), mp 139°С. IR spectrum, ν, cm : 1725
3
1
(C=O). H NMR spectrum (CDCl ), δ, ppm: 1.21 t
3
C H IO P, space group P2 2 2 , Z 4, a 9.9307(3), b
2
4
26
2
1 1 1
(
6H, OCH CH , J = 7.1 Hz), 2.72 t (4H, CH COO, J =
2 3 2
3
1
1
2.9676(3), c 18.0285(5) Å, V 2321.79(11) Å , d
.443 g/cm , μ 1.464 mm , 38960 (±13, ±17, ±24)
calc
7
.2 Hz), 3.39 t (4H, PCH , J = 7.2 Hz), 4.06 q (4H,
3
–1
2
13
OCH CH , J = 7.1 Hz), 7.91–7.75 m (10H, ArН). С
2
3
reflections collected over θ from 1.93° to 28.72°, 6010
NMR spectrum (CDCl ), δ , ppm: 14.14 (OCH CH ),
3
С
2
3
of them were independent (R 0.0223) and 5321 were
int
1
2
8
9
8.41 d (PCH , J = 53.5 Hz), 27.31 d (CH COO, J =
2
2
observed with I ≥ 2σ(I), 259 parameters were refined,
R 0.0268, wR 0.0656, maximum residual electron
ipsо
.8 Hz), 62.13 (OCH CH ), 116.23 d (С , J =
2
3
o
m
1
2
4.2 Hz), 130.94 d (С , J = 12.4 Hz), 133.26 d (С , J =
.6 Hz), 135.65 d (С , J = 2.7 Hz), 170.42 d (COOEt,
3
density was 0.701 (–0.384) e/Å . Crystallographic data
were deposited at the Cambridge Crystallographic
Data Center (CCDC 1556935).
p
31
J = 11.3 Hz). P NMR spectrum: δ 28.75 ppm.
Р
Found, %: C 34.33; H 3.48; P 4.01. C H I O P. Cal-
22
28 3
4
culated, %: C 34.39; H 3.65; P 4.04.
Crystals of compound 16 were triclinic, crystal di-
mensions were 0.098×0.198×0.402 mm , M 768.11 g/mol,
3
Bis(3-methoxy-3-oxopropyl)diphenylphosphnium
iodide (17). A solution of 2 g (14.1 mmol) of methyl
iodide in 10 mL of anhydrous methanol was added to a
solution of 0.24 g (0.73 mmol) of 3-[(2-carboxyethyl)-
diphenylphosphyno]propanoate in 10 mL of the same
solvent. The reaction mixture was heated in a water
bath for 20 h. After the reaction was complete, excess
of methyl iodide and methanol was eliminated on a
rotor evaporator. The formed orange oily product was
washed several times with methanol and dried under
C H I O P, space group P-1, Z 2, a 10.7376(9), b
2
2
28 3
4
1
1
1
2.5268(10), c 12.6711(10) Å, α 116.086(3), β
3
01.924(3)°, γ 104.760(3)°, V 1377.0(2) Å , d
calc
3
–1
.853 g/cm , μ 3.468 mm , 79220 (±14, ±16, ±17)
reflections were collected over θ from 1.91° to 28.66°,
071 of them were independent (R 0.0337) and 5162
7
int
were observed with I ≥ 2σ(I), 281 parameters were
refined, R 0.0392, wR 0.0850, maximum residual
1
2
3
electron density was 1.256 (–1.138) e/Å . Crystallo-
graphic data were deposited at the Cambridge Crys-
tallographic Data Center (CCDC 1556934).
–
1
vacuum. Yield 0.26 g (57%). IR spectrum, ν, cm :
1
1
2
3
729 s (C=O). H NMR spectrum (CDCl ), δ, ppm:
3
.75 t (4H, CH COO, J = 6.9 Hz), 3.55 s (3H, OCH ),
.65 t (4H, PCH , J = 6.9 Hz), 7.68–7.97 m (10H,
ArН). С NMR spectrum (CDCl ), δ , ppm: 18.04 d
2
3
(
4-Ethoxy-4-oxobutyl)triphenylphosphonium iodide
2). A solution of 0.47 g (0.309 mmol) of ethyl iodide
in 5 mL of acetonitrile was added to a solution of 0.36 g
0.103 mmol) of 4-(triphenylphosphino)butanoate in
mL of acetonitrile at room temperature at continuous
2
(
1
3
3
С
(
5
(
(
PCH , J = 53.0 Hz), 26.92 d (CH COO, J = 2.4 Hz),
2
2
(
5
ipso
2.59 (OCH ), 116.45 d (С , J = 83.9 Hz), 130.55 d
3
o
m
С , J = 12.3 Hz), 133.38 d (С , J = 9.7 Hz), 135.31 d
stirring. After the reaction was complete, colorless
crystals were repeatedly washed with anhydrous
diethyl ether and dried under vacuum, mp 141°С.
p
31
С , J = 2.4 Hz), 170.93 d (COOCH , J = 11.6 Hz). P
3
NMR spectrum: δ 29.24 ppm. Found, %: C 32.19; H
Р
–
1
3.14; P 4.15. C20
3.24; P 4.19.
H I O P. Calculated, %: C 32.45; H
24 3 4
Yield: 0.656 g (79%), mp 127°С. IR spectrum, ν, cm :
1
1
720 (C=O). H NMR spectrum (СDCl ), δ, ppm: 1.23
3
t (3H, OCH CH , J = 7.1 Hz), 1.73 m (2Н, РСН СН ,
Bis(3-isopropoxy-3-oxopropyl)diphenylphosphnium
iodide (18). A solution of 2 g (14.1 mmol) of methyl
iodide in 10 mL of anhydrous isopropanol was added
to a solution of 0.24 g (0.73 mmol) of 3-[(2-carboxy-
ethyl)diphenylphosphyno]propanoate in 10 mL of the
same solvent. The reaction mixture was heated in a
2
3
2
2
J = 7.1 Hz), 2.42 t (2H, CH COO, J = 7.2 Hz), 2.79 t
2
(
7
2H, PCH , J = 7.2 Hz), 4.17 m (2H, OCH CH , J =
.1 Hz), 7.41–7.67 m (15H, ArН). P NMR spectrum:
2
2
3
3
1
δ 23.27 ppm. Found, %: С 57.07; Н 5.51. C H IO P.
Р
24 26
2
Calculated, %: С 57.14; Н 5.16.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 12 2017

THE INFLUENCE OF SOLVENTS ON THE ALKYLATION
2793
water bath during 20 h. Needle-shaped crystals were
filtered off, washed several times with diethyl ether
and dried under vacuum, mp 135°С. Yield 0.31 g
Elem., 1999, vol. 147, p. 91. doi 10.1080/
0426509908053526
1
3
4
. Galkin, V.I., Bakhtiyarova, Yu.V., Polezhaeva, N.A., Gal-
kina, I.V., Cherkasov, R.A., Krivolapov, D.B., Gubaidu-
llin, A.T., and Litvinov, I.A., Russ. J. Gen. Chem., 2002,
vol. 72, no. 3, p. 376. doi 10.1080/ 10426509908053526
. Galkin, V.I., Bakhtiyarova, Yu.V., Polezhaeva, N.A.,
Galkina, I.V., Cherkasov, R.A., Krivolapov, D.B.,
Gubaidullin, A.T., and Litvinov, I.A., Russ. J. Gen. Chem.,
2002, vol. 72, no. 3, p. 384. doi 10.1023/A:1015487416152
5. Galkin, V.I., Bakhtiyarova, Yu.V., Sagdieva, R.I.,
Galkina, I.V., Cherkasov, R.A., Krivolapov, D.B.,
Gubaidullin, A.T., and Litvinov, I.A., Russ. J. Gen.
Chem., 2006, vol. 76, no. 3, p. 430. doi 10.1134/
S1070363206030133.
. Galkin, V.I., Bakhtiyarova, Yu.V., Sagdieva, R.I.,
Galkina, I.V., and Cherkasov, R.A., Heteroatom.
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. Bakhtiyarova, Yu.V., Sagdieva, R.I., Galkina, I.V.,
Galkin, V.I., Cherkasov, R.A., Krivolapov, D.B.,
Gubaidullin, A.T., and Litvinov, I.A., Russ. J. Org.
Chem., 2007, vol. 43, no. 2, p. 207. doi 10.1134/
S1070428007020091
–
1
1
(
67.4%). IR spectrum, ν, cm : 1720 (C=O). H NMR
spectrum (CDCl ), δ, ppm: 1.18 d [12H, OCH(CH ) ,
3
3 2
J = 6.2 Hz], 2.68 t (2H, CH COO, J = 7.1 Hz), 3.37 t
2
(
(
2H, PCH , J = 7.1 Hz), 4.89 m (1H, OCH), 7.82 m
10H, ArH). С NMR spectrum (CDCl ), δ , ppm:
3 C
2
1
3
1
2
1
1
1
8.39 d (PCH , J = 53.5 Hz), 21.77 [OCH(CH ) ],
2
3
2
7.55 d (CH COO, J = 2.8 Hz), 69.99 [OCH(CH ) ],
2
3 2
ipso
o
16.35 d (С , J = 84.3 Hz), 130.92 d (С , J = 12.4 Hz),
m
p
33.26 d (С , J = 9.6 Hz), 135.59 d (С , J = 2.8 Hz),
3
1
69.94 d (COO, J = 11.0 Hz). P NMR spectrum
(
CDCl ): δ 28.86 ppm. Found, %: C 35.94; H 3.95; P
3 Р
6
3
.55. C H I O P. Calculated, %: C 36.18; H 4.02; P 3.89.
24 32 3 4
(
2-Carboxyethyl)(methyl)diphenylphosphonium
7
iodide (19). A solution of 2 g (14.1 mmol) of methyl
iodide in 10 mL of anhydrous isopropanol and several
drops of H O were added to a solution of 0.24 g
2
(
0.73 mmol) of 3-[(2-carboxyethyl)diphenylphosphyno]-
propanoate in 10 mL of the same solvent. The reaction
mixture was heated in a water bath during 20 h. After
the reaction was complete, excess of methyl iodide,
isopropanol, and water was eliminated on a rotor
evaporator. The obtained product was washed several
times with diethyl ether on a porous glass filter and
dried under vacuum. Yield 0.22 g (77%), mp 210°С.
8
. Galkin, V.I., Salin, A.V., Bakhtiyarova, Yu.V., and
Sobanov, A.A., Russ. J. Gen. Chem., 2009, vol. 79,
no. 5, p. 919. doi 10.1134/S1070363209050090
9. Romanov, S.R. Aksunova, A.F., Islamov, D.R.,
Dobrynin, A.B., Krivolapov, D.B., Kataeva, O.N.,
Bakhtiyarova, Yu.V., Gnezdilov, O.I., Galkina, I.V.,
and Galkin, V.I., Phosphorus, Sulfur, Silicon, Relat.
Elem., 2016, vol. 191, nos. 11–12, p. 1637. doi 10.1080/
–
1
1
IR spectrum, ν, cm : 1715 (C=O). H NMR spectrum
1
0426507.2016.1223661
(
D O), δ, ppm: 2.31 t (2H, CH COO, J = 7.6 Hz), 2.38 s
2
2
1
0. Bakhtiyarova, Yu.V., Minnullin, R.R., Galkina, I.V.,
(
3H, PCH ), 2.98 t (2H, PCH , J = 7.6 Hz), 7.71–7.49
3
2
Cherkasov, R.A., and Galkin, V.I., Russ. J. Gen. Chem.,
1
3
m (10H, ArН). С NMR spectrum (D O), δ , ppm:
2
С
2
015, vol. 85, no. 9, p. 2037. doi 10.1134/
6
2
8
1
.03 d (PCH , J = 56.3 Hz), 19.26 d (PCH , J = 53.5 Hz),
3
2
S1070363215090042
ipso
8.87 d (CH COO, J = 3.1 Hz), 118.98 d (С , J =
2
11. Bakhtiyarova, Yu.V., Aksunova, A.F., Minnullin, R.R.,
Galkina, I.V., and Galkin, V.I., Russ. Chem. Bull., 2016,
vol. 65, no. 5, p. 1308. doi 10.1007/s11172-016-1453-5
12. Bakhtiyarova, Yu.V., Minnullin, R.R., Morozov, M.V.,
Bakhtiyarov, D.I., Islamov, D.R., Dobrynin, A.B.,
Kataeva, O.N., Cherkasov, R.A., Galkin, V.I., and
Galkina, I.V., Phosphorus, Sulfur, Silicon, Relat. Elem.,
2016, vol. 191, nos. 11–12, p. 1633. doi 10.1080/
o
m
6.3 Hz), 129.95 d (С , J = 12.5 Hz), 132.05 d (С , J =
p
0.1 Hz), 134.70 d (С , J = 2.6 Hz), 177.82 d (COOH,
3
1
J = 13.7 Hz). P NMR spectrum (D O): δ 23.29 ppm.
2
Р
Found, %: C 47.71; H 4.32; P 7.68. C H IO P.
16
18
2
Calculated, %: C 48.00; H 4.50; P 7.75.
ACKNOWLEDGMENTS
1
0426507.2016.1223660.
This work was financially supported by subsidy for
Kazan Federal University in the frame of the govern-
mental task in the research field (no. 4.5888.2017/8.9).
1
1
3. Bruker. APEX2 Software Suite for Crystallographic
Programs, Bruker AXS, Inc., Madison, WI, USA, 2009.
4. Bruker. Area detector control and integration software.
Version 5.x. SMART and SAINT. Madison, Wisconsin
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 12 2017