Synthesis and structure of tetra- and triphenylantimony organosulfonates

Article abstract of DOI:10.1023/B:RUCO.0000011636.28262.d3

Tetraphenylantimony 2-naphthalenesulfonate (I), tetraphenylantimony phenylmethanesulfonate (II), and bis(tetraphenylantimony) sulfate (III) were synthesized via reaction of pentaphenylantimony with 2-naphthalenesulfonic acid, triphenylantimony bis(phenylmethanesulfonate), and triphenylantimony sulfate, respectively, in toluene. Triphenylantimony bis(phenylmethanesulfonate) (IV) was synthesized from triphenylstibine, phenylmethanesulfonic acid, and hydrogen peroxide (taken in the molar ratio of 1:2:1). Organoantimony betaine Ph ₃S⁺bCH(Ph)SO₂O (V) was obtained by reacting triphenylstibine with phenylmethanesulfonyl chloride in the presence of hydrogen peroxide. The structures of the compounds synthesized were determined using X-ray diffraction analysis. The Sb atoms in I-IV have distorted trigonal bipyramidal coordination. The Sb-C and Sb-O distances are equal to 2.100(4)-2.140(3) and 2.644(2) A in molecule I, 2.105(2)-2.131(2) and 2.699(1) A in II, 2.096(6)-2.169(6) and 2.101(6), 2.271(3) A in III, and 2.101(3)-2.102(5) and 2.111(2) A in IV. In V, the Sb atoms have close tetrahedral (2.105-2.115 A) and remote (2.65, 3.019 A) octahedral environment (the oxygen atoms of sulfo group of their own and neighboring molecules). Two betaine molecules are joined through the O atoms of the sulfo groups of bidentate phenylmethanesulfonate ligands to form a centrosymmetrical dimer. The intermolecular C(1)-H(1)...O(1) hydrogen bonds (3.10 A) are formed that strengthen the dimer.

Full text of DOI:10.1023/B:RUCO.0000011636.28262.d3

Russian Journal of Coordination Chemistry, Vol. 30, No. 1, 2004, pp. 13–22. Translated from Koordinatsionnaya Khimiya, Vol. 30, No. 1, 2004, pp. 15–24.
Original Russian Text Copyright © 2004 by Sharutin, Sharutina, Pakusina, Platonova, Gerasimenko, Bukvetskii, Pushilin.
Synthesis and Structure of Tetra-
and Triphenylantimony Organosulfonates
V. V. Sharutin*, O. K. Sharutina*, A. P. Pakusina*, T. P. Platonova*,
A. V. Gerasimenko**, B. V. Bukvetskii**, and M. A. Pushilin**
*Blagoveshchensk State Pedagogical University, ul. Lenina 104, Blagoveshchensk, 675000 Russia
**Institute of Chemistry, Far East Division, Russian Academy of Sciences,
pr. Stoletiya Vladivostoka 109, Vladivostok, 690022 Russia
Received December 24, 2002
Abstract—Tetraphenylantimony 2-naphthalenesulfonate (I), tetraphenylantimony phenylmethanesulfonate
(II), and bis(tetraphenylantimony) sulfate (III) were synthesized via reaction of pentaphenylantimony with
2-naphthalenesulfonic acid, triphenylantimony bis(phenylmethanesulfonate), and triphenylantimony sulfate,
respectively, in toluene. Triphenylantimony bis(phenylmethanesulfonate) (IV) was synthesized from triphenyl-
stibine, phenylmethanesulfonic acid, and hydrogen peroxide (taken in the molar ratio of 1 : 2 : 1). Organoanti-
+
–
mony betaine
(V) was obtained by reacting triphenylstibine with phenylmethanesulfonyl
Ph3SbCH(Ph)SO2O
chloride in the presence of hydrogen peroxide. The structures of the compounds synthesized were determined
using X-ray diffraction analysis. The Sb atoms in I–IV have distorted trigonal bipyramidal coordination. The
Sb–C and Sb–O distances are equal to 2.100(4)–2.140(3) and 2.644(2) Å in molecule I, 2.105(2)–2.131(2) and
2.699(1) Å in II, 2.096(6)–2.169(6) and 2.101(6), 2.271(3) Å in III, and 2.101(3)–2.102(5) and 2.111(2) Å in
IV. In V, the Sb atoms have close tetrahedral (2.105–2.115 Å) and remote (2.65, 3.019 Å) octahedral environ-
ment (the oxygen atoms of sulfo group of their own and neighboring molecules). Two betaine molecules are
joined through the O atoms of the sulfo groups of bidentate phenylmethanesulfonate ligands to form a cen-
trosymmetrical dimer. The intermolecular ë(1)–ç(1)···é(1) hydrogen bonds (3.10 Å) are formed that
strengthen the dimer.
Pentaorganylantimony is known to react with anti-
Bis(tetraphenylantimony) sulfate (III) was synthe-
mony derivatives R3SbX2, where R is Ar or Alk and X is sized in the yield of 53% using similar scheme (toluene,
the acid residue, (toluene, 1 h, 90°ë) and form R4SbX 4 h, 90°C):
compounds in a high yield [1–18]. In the course of our
Ph5Sb + Ph3SbSO4
(Ph4Sb)2SO4.
(III)
studies in this field of chemistry of antimony com-
pounds, we established that an increase in the size of sub-
stituent X hinders this reaction. Thus, triphenylantimony
bis(2-naphthalenesulfonate) fails to react with pentaphe-
nylantimony under the mentioned conditions, although
the reaction between pentaphenylantimony and 2-naph-
thalenesulfonic acid gives tetraphenylantimony 2-naph-
thalenesulfonate (I) in 80% yield. Bulky arenesulfonate
ligands at the antimony atom are likely to hinder the for-
mation of a labile ionic complex, which, as we suggest,
forms at the first stage of the reaction and decomposes
further to yield tetraphenylantimony arenesulfonate:
The yield of complex III obtained from bisulfate
and pentaphenylantimony under these conditions was
higher (79%):
Ph5Sb + Ph4SbOSO3H
(Ph4Sb)2SO4 + PhH.
(III)
The antimony compounds Ph3Sbï2 with symmetri-
cal structure were synthesized from triphenylstibine,
sulfonic acid, and hydrogen peroxide via the reactions
of oxidative addition:
Ph5Sb + Ph3Sb(OSO2Ar)2
[Ph4Sb]+[Ph4Sb(OSO2Ar)2]–
2Ph4SbOSO2Ar.
Ph3Sb + 2HOSO2R + H2O2
Ph3Sb(OSO2R)2 + 2H2O.
Thus,
tetraphenylantimony
phenylmethane-
In this reaction, triphenylantimony bis(phenyl-
methanesulfonate) (IV) was obtained in the yield of
91%; however, the yields of triphenylantimony bis(2-
naphthalenesulfonate) and triphenylantimony bis(1-
naphthalenesulfonate) were 46 and 25%, respectively,
which is likely to be due to the increasing size of the
organic fragment of arenesulfonate ligand.
sulfonate (II) was the only product (yield 97%) of reac-
tion of pentaphenylantimony with triphenylantimony
bis(phenylmethanesulfonate):
Ph5Sb + Ph3Sb(OSO2CH2Ph)2
2Ph4SbOSO2CH2Ph.
(II)
1070-3284/04/3001-0013 © 2004 åÄIä “Nauka /Interperiodica”

14
SHARUTIN et al.
C(45)
C(44)
C(46)
C(13)
C(43)
C(14)
C(12)
C(41)
C(15)
O(2)
C(42)
C(11)
S
O(1)
C(16)
C(22)
C(23)
C(24)
O(3)
C(2)
C(3)
Sb
C(21)
C(1)
C(5)
C(10)
C(9)
C(31)
C(32)
C(4)
C(36)
C(35)
C(26)
C(25)
C(8)
C(33)
C(7)
C(6)
C(34)
Fig. 1. Structure of tetraphenylantimony 2-naphthalenesulfonate (I).
We established that reaction of triphenylstibine with aroxides [19–22], in which this bond can be considered
phenylmethanesulfonyl chloride in the presence of as a low-polarity covalent bond.
hydrogen peroxide follows a different course and
Note that in antimony derivatives Ar4SbX (X is the
results in organoantimony betaine (V):
residue of a strong acid), the Sb–X bond is, as a rule, an
ionic bond. Thus, the crystal of triphenylantimony
bisulfate consists of tetraphenylstibonium cations and
hydroxysulfate anions [23]. The replacement of acid
hydrogen atom in this compound by the electron-donor
group Ph4Sb decreases the accepting properties of the
sulfate group, which is followed by a decrease in the
Sb–O bond polarity and in its strengthening. A shorten-
ing of the Sb(1)–O(4) and Sb(2)–O(1) bonds in III
makes the Ph4Sb fragments approach the sulfur atom
and, as a consequence, makes the O(2)···Sb(2) and
O(3)···Sb(1) distances reduce to 3.737(4) and 3.411(4) Å,
respectively. The former value insignificantly exceeds
the sum of the van der Waals radii of the oxygen and
sulfur atoms, while the latter makes 92% of this sum,
thus suggesting the donor–acceptor interaction
between the O(3) and Sb(1) atoms.
+
–
H2O2
Ph3Sb + ClSO2CH2Ph
Ph3SbCH(Ph)SO2O.
(V)
According to X-ray diffraction data, the antimony
atoms in molecules I and II have heavily distorted tri-
gonal bipyramidal coordinations with the axial sul-
fonate ligands (Figs. 1, 2). The Sb–Ceq bond lengths
and OSbOax angle in compounds I (2.100(4), 2.104(4),
2.114(4) Å; 177.2(1)°) and II (2.105(2), 2.105(2),
2.105(2) Å; 177.04(5)°) are almost equal. In structures
I and II, the Sb–Cax and Sb–O bond lengths are some-
what different (2.140(3), 2.644(2) Å in I and 2.131(2),
2.699(1) Å in II). When analyzing the geometrical
parameters of structurally characterized tetraphenylan-
timony sulfonates (Table 1), one can see that the Sb–O
distances vary within wide intervals, the longest dis-
tance being found in compound II.
Alkanesulfonate groups in molecule IV (Fig. 4) are
in the axial position, while the Ph substituents are in the
In complex III (Fig. 3), the equatorial CSbC angles equatorial positions. The sum of the equatorial bond
(111.8(3)°–124.9(3)°) are close to 120°; the sums of the angles is equal to 360°, the OSbO angle is equal to
equatorial angles are equal to 358.3° (Sb(1)) and 357.6° 175.8(1)°. Thus, in molecule IV, the Sb atom has a dis-
(Sb(2)); the Sb–O (2.248(3) and 2.271(3) Å) distances torted trigonal bipyramidal coordination. The Sb–O
are close to the analogous distances in tetraphenylanti- (2.101(3), 2.102(5) Å) and Sb–C (2.111 (2) Å) bond
mony oximates [9, 13, 16, 17] and tetraphenylantimony lengths are standard for antimony(V) compounds of the
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 30 No. 1 2004

SYNTHESIS AND STRUCTURE
15
O(2)
C(56)
C(55)
C(54)
O(3)
C(43)
S
C(44)
C(45)
C(42)
C(51)
C(50)
O(1)
C(25)
C(24)
C(52)
C(53)
C(46)
C(23)
C(41)
C(26)
C(36)
C(21)
C(22)
Sb
C(35)
C(34)
C(31)
C(32)
C(11)
C(16)
C(12)
C(33)
C(13)
C(15)
C(14)
Fig. 2. Structure of tetraphenylantimony phenylmethanesulfonate (II).
C(64)
C(34)
C(65)
C(33)
C(32)
C(63)
C(35)
C(66)
C(61)
C(62)
C(36)
C(45)
C(46)
C(44)
C(43)
C(31)
C(26)
C(86)
C(85)
C(84)
O(1)
C(76)
C(71)
O(3)
Sb(2)
C(81)
Sb(1)
C(41)
C(25)
C(42)
C(72)
S
C(75)
C(51)
C(83)
O(4)
C(56)
C(21)
C(82)
C(24)
C(11)
C(73)
O(2)
C(22)
C(23)
C(74)
C(12)
C(55)
C(54)
C(52)
C(16)
C(53)
C(13)
C(14)
C(15)
Fig. 3. Structure of bis(tetraphenylantimony) sulfate (III).
Ar3SbX2 type [24]. Molecule IV has its own symmetry 122.0(1)° range. Two molecules V are joined through
ë2 with a twofold axis passing through the Sb, C(31),
the hydrogen bond between the hydrogen atom of the
methine group and the oxygen atom of the sulfonate
ligand, this O atom being coordinated to the Sb atom of
another molecule (the Sb–O(1)' distance is equal to
3.019(2) Å). In addition, the distance between O(3) and
Sb atoms in molecule V is equal to 2.988(2) Å. The
and C(34) atoms.
According to elemental and X-ray diffraction analy-
ses data, betaine
V
is the crystal solvate
Ph3SbCH(Ph)SO3 · C7H8. The antimony atom in this
compound has a distorted tetrahedral coordination
(Fig. 5). The CSbC angles vary within the 98.7(1)°– length of one of the S–O bonds in the sulfo group
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 30 No. 1 2004

16
SHARUTIN et al.
Table 1. Selected bond lengths and angles in tetraphenylan-
timony sulfonates with the general formula Ph4SbOSO2R
respectively) are close to the values of angles in octahe-
dral complexes.
Bond lengths, Å
Angle
OSbCax, deg
EXPERIMENTAL
R
Sb–Ceq Sb–Cax Sb–O
Synthesis of complex I. A mixture of 0.50 g of pen-
taphenylantimony and 0.20 g of 2-naphthalenesulfonic
acid in 20 ml of toluene was kept at 20°ë for 1 h; the
solvent was removed; the residue was recrystallized
from water. The yield was 0.50 g (80%); mp 199°C.
Synthesis of complex II. A mixture of 1.00 g of
pentaphenylantimony, 1.37 g of triphenylantimony
bis(phenylmethanesulfonate) and 20 ml of toluene was
kept at 90°C for 1 h. After cooling, the colorless crys-
tals were filtered off and dried. The yield was 2.16 g
(91%); mp 196°C.
PhCH2
2.105(2) 2.131(2) 2.699(1) 177.04(5)
2.105(2)
2.105(2)
C6H3(COOH)-3, 2.092(3) 2.118(3) 2.691(3) 174.5(1)
(OH)-4 [2]
2.097(3)
2.118(3)
Synthesis of complex III. a) A mixture of 1.00 g of
pentaphenylantimony and 0.89 g of triphenylantimony
sulfate in 15 ml of toluene was heated at 90°ë for 4 h.
The solvent was removed. The product was recrystal-
lized from water. The yield of colorless crystals III was
1.00 g (53%); mp 230°C.
b) A mixture of 1.00 g of pentaphenylantimony and
1.04 g of tetraphenylantimony bisulfate in 10 ml of tol-
uene was heated at 90°ë for 1 h. The solvent was
removed. The yield of crystal complex III was 1.50 g
(79%); mp 230°C.
Synthesis of complex IV. To a mixture of 0.50 g of
triphenylantimony and 0.48 g of phenylmethane-
sulfonic acid in 20 ml of ether, 0.16 ml of 30% hydro-
gen peroxide solution was added. After 12 h, the sol-
vent was removed; the residue was recrystallized from
toluene. The yield of colorless crystals IV was 0.70 g
(71%), mp 193°C.
Triphenylantimony bis(1-naphthalenesulfonate)
was synthesized by a procedure similar to that for com-
plex IV. The yield was 25%; mp 221°C.
2-C10H7
2.100(4) 2.140(3) 2.644(2) 177.2(1)
2.104(4)
2.114(4)
C6H4Me-4 [1]
C6H5 [25]
2.099(4) 2.129(4) 2.588(4) 178.2(2)
2.101(4)
2.119(4)
2.104(5) 2.131(5) 2.506(4) 176.0(2)
2.108(6)
2.111(6)
C6H3Me2-2,4 [3] 2.101(6) 2.131(6) 2.464(4) 175.2(2)
2.102(6)
2.111(7)
OSbPh4
2.096(6)
Triphenylantimony bis(2-naphthalenesulfonate)
was synthesized using procedures similar to those used
in the synthesis of complex IV. The yield was 46%; mp
227°C.
2.118(6) 2.178(6) 2.248(3) 174.8(2)
2.109(6)
Synthesis of complex V. To a mixture of 0.50 g of
triphenystibine and 0.28 g of phenylmethanesulfonyl
chloride in 20 ml of diethyl ether, 0.16 ml of 30%
hydrogen peroxide solution was added. The reaction
mixture was kept at 20°ë for 12 h; the solvent was
removed; the residue was recrystallized from toluene.
The yield was 0.90 g (91%); mp 232°C (with decompo-
sition).
X-ray diffraction analysis of natural-faceted single
crystals of complexes I–V was carried out on a Bruker
SMART 1000 CCD diffractometer (λMoKα radiation).
Structures I–V were solved by direct methods and
2.101(6)
2.124(5)
2.095(3) 2.169(6) 2.271(3) 174.1(2)
(S−O(2), 1.433(2) Å) noticeably differs from those of
the remaining two bonds (S–O(1, 3), 1.446(2), 1.454(2)
Å, respectively), which can be explained only by an
additional interaction of the O(1, 3) atoms with the Sb
and H atoms of the methine group.
Thus, in complex V, the coordination number of the refined by the least-squares method in an anisotropic
central atom is increased to six. This suggestion is sup- approximation for non-hydrogen atoms. Positions of
ported by the fact that the values of the C(21)SbO(3) the hydrogen atoms were calculated geometrically and
and C(41)SbO(1)' angles (164.26(9)° and 175.66(9)°, included in the refinement in the rider model.
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 30 No. 1 2004

SYNTHESIS AND STRUCTURE
17
Table 2. Crystallographic data and results of refinement of structures I–V
Value
Parameter
I
II
III
IV
V
Empirical formula
C34H27O3SSb
637.37
C31H27O3SSb
601.34
C48H40O4SSb2
956.36
C32H29O6S2Sb
695.42
C32H29O3SSb
615.36
M
T, K
293(2)
293(2)
296(2)
297(2)
296(2)
Crystal system
Orthorhombic
Triclinic
Monoclinic
Monoclinic
Triclinic
Space group
P212121
P21/c
C2/c
P1
P1
Unit cell parameters:
a, Å
10.1258(12)
15.8458(19)
17.687(2)
90
9.278(1)
10.680(1)
13.918(2)
96.737(2)
99.606(2)
98.345(2)
1331.2(3)
2
12.645(3)
26.714(5)
12.299(2)
90
19.296(3)
9.405(1)
17.343(2)
8.618(1)
9.923(1)
16.233(2)
87.729(2)
88.857(2)
86.001(2)
1383.5(3)
2
b, Å
c, Å
α, deg
β, deg
γ, deg
V, Å3
Z
90
97.293(5)
90
99.782(3)
90
2837.8(6)
4
4121.0(14)
4
3101.6(7)
4
ρ(alcd), g/cm3
1.492
1.500
1.541
1.489
1.066
1408
1.477
µ
Mo, mm–1
1.079
1.145
1.405
1.104
F(000)
1288
608
1912
624
Crystal form (size, mm)
Prism
Prism
Prism
Prism
Prism
(0.15 × 0.20 × 0.25) (0.20 × 0.25 × 0.28) (0.10 × 0.15 × 0.25) (0.20 × 0.20 × 0.05) (0.20 × 0.20 × 0.20)
θ, deg
1.73–30.00
3.00–29.00
1.79–20.06
2.14–24.05
3.03–26.03
Range of reflection
indices
–12 ≤ h ≤ 14
–20 ≤ k ≤ 22
–24 ≤ l ≤ 23
–12 ≤ h ≤ 12
–14 ≤ k ≤ 14
–18 ≤ l ≤ 18
–12 ≤ h ≤ 8
–25 ≤ k ≤ 25
–11 ≤ l ≤ 11
–21 ≤ h ≤ 22
–10 ≤ k ≤ 10
–16 ≤ l ≤ 19
–10 ≤ h ≤ 10
–12 ≤ k ≤ 12
–19 ≤ l ≤ 20
Total number
of reflections
20681
13858
12316
7155
14750
Total number
of unique reflections
8051
(Rint = 0.0528)
6996
(Rint = 0.0251)
3860
(Rint = 0.0338)
2447
(Rint = 0.0773)
5442
(Rint = 0.0528)
Reflections
4352
353
6096
2952
1866
3814
with I > 2σ(I)
Number of refined
parameters
325
496
187
325
GOOF
0.789
0.980
0.899
1.009
0.877
R-factors
for all reflections
R1 = 0.0723
wR2 = 0.0667
R1 = 0.0333
wR2 = 0.0745
R1 = 0.0423
wR2 = 0.0571
R1 = 0.0687
wR2 = 0.0972
R1 = 0.0615
wR2 = 0.0865
Final R-factor
(I > 2σ(I))
R1 = 0.0334
wR2 = 0.0599
R1 = 0.0283
wR2 = 0.0728
R1 = 0.0277
wR2 = 0.0541
R1 = 0.0446
wR2 = 0.0871
R1 = 0.0388
wR2 = 0.0809
Residual electron densi-
0.362/0.350
0.412/0.963
0.271/0.382
0.356/0.492
0.379/0.573
ty (min/max), e/Å3
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 30 No. 1 2004

18
SHARUTIN et al.
Table 3. Coordinates of atoms (×104) and their isotropic equivalent thermal parameters in structures I–V
Atom
Sb
S
O(1)
O(2)
O(3)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
C(8)
C(9)
C(10)
C(11)
C(12)
C(13)
C(14)
C(15)
C(16)
C(21)
C(22)
C(23)
C(24)
C(25)
C(26)
C(31)
C(32)
C(33)
C(34)
C(35)
C(36)
C(41)
C(42)
x
y
z
Ueq, Å2
Atom
x
y
z
Ueq, Å2
I
II
1710.3(2)
1512(1)
8539(3)
8936(4)
9114(3)
6784(5)
5871(5)
4564(5)
4068(5)
2707(5)
2298(5)
3202(6)
4526(5)
4992(4)
6348(4)
2789(4)
2410(4)
3100(5)
4159(5)
4544(3)
3849(4)
2011(3)
1401(4)
1644(5)
2493(5)
3123(7)
2863(5)
2469(4)
3672(4)
4135(5)
3392(8)
2184(6)
1727(5)
–333(3)
–982(4)
6898.8(1)
4396.1(6)
10239(1)
8797(2)
9379(3)
9178(2)
9399(2)
9287(3)
8922(3)
8759(3)
8367(3)
8123(3)
8283(3)
8682(2)
8833(2)
6611(2)
5973(2)
5845(2)
6333(3)
6975(3)
7113(2)
8234(2)
8772(2)
9631(2)
9949(3)
9415(3)
8556(3)
6557(2)
6175(2)
5994(3)
6198(3)
6568(3)
6762(2)
6705(2)
6205(2)
6084(3)
6447(3)
6952(4)
7073(3)
II
3439.6(1)
3687.6(6)
1606(2)
1818(3)
570(3)
1166(2)
1745(2)
1636(3)
959(3)
839(4)
188(4)
–348(3)
–267(3)
390(2)
41.64(7) C(14)
9801(2)
13662(2)
13065(2)
11983(2)
9801(1)
10971(2)
11063(2)
10006(2)
8853(2)
8730(2)
8390(1)
8348(2)
7477(2)
6685(2)
6720(2)
7574(2)
10127(1)
9246(2)
9593(2)
10795(2)
11669(2)
11342(2)
5091(2)
4960(1)
5499(2)
5371(2)
4671(2)
4126(2)
4280(2)
III
6218(1)
4042(1)
5339(1)
4887(1)
5198(1)
5719(1)
5518(1)
6016(2)
5528(2)
5431(2)
5814(3)
6301(3)
6400(2)
6649(2)
6774(3)
7097(3)
7303(3)
7175(3)
6840(2)
7007(2)
7809(2)
7957(1)
8951(1)
9514(1)
10527(1)
10971(1)
10424(1)
9396(1)
6744(1)
7219(2)
6831(2)
5978(2)
5499(1)
5887(1)
6771(1)
6135(1)
5802(1)
6110(2)
6739(1)
7059(1)
7073(1)
8056(1)
8335(2)
9301(2)
9880(2)
9608(2)
8704(1)
64.8(5)
64.4(5)
54.8(4)
41.7(3)
57.7(4)
67.3(5)
67.2(6)
67.5(5)
55.1(4)
42.7(3)
61.5(5)
76.8(6)
72.4(5)
76.9(6)
59.8(5)
38.6(3)
53.0(4)
65.0(5)
62.8(5)
56.6(4)
47.8(4)
63.2(5)
51.6(4)
79.6(7)
96.0(9)
84.1(7)
70.0(5)
57.9(5)
58.4(3)
65.8(7)
169(2)
140(2)
47.4(8)
64(1)
72(1)
56(1)
80(2)
94(2)
89(2)
71(1)
51(1)
52(1)
40.8(9)
58(1)
63(1)
70(1)
58(1)
49(1)
44.9(8)
53(1)
64(1)
78(1)
89(2)
71(1)
47(1)
63(1)
85(2)
87(2)
80(2)
64(1)
40.8(9)
48(1)
61(1)
63(1)
62(1)
52(1)
C(15) 10159(2)
C(16)
C(21)
C(22)
C(23)
C(24)
C(25)
C(26)
C(31)
C(32)
C(33)
C(34)
C(35)
C(36)
C(41)
C(42)
C(43)
C(44)
C(45)
C(46)
C(50)
C(51)
C(52)
C(53)
C(54)
C(55)
C(56)
9257(2)
6894(2)
6930(2)
7114(2)
7281(2)
7254(2)
7048(2)
7708(2)
9127(2)
9931(2)
9338(2)
7931(3)
7084(2)
4531(2)
3453(2)
2086(2)
1808(2)
2896(2)
4258(2)
5125(2)
6015(2)
7474(2)
8268(2)
7555(3)
6123(2)
5350(2)
513(2)
2456(2)
1966(2)
1307(2)
1140(2)
1611(3)
2273(2)
3490(2)
2995(2)
3023(2)
3547(3)
4041(2)
4019(2)
4510(2)
4588(3)
5309(3)
5921(3)
5839(3)
5135(2)
3333(2)
3847(2)
3760(3)
3161(3)
2655(2)
2734(2)
Sb(1)
Sb(2)
S
2074(1)
2485(1)
3069(1)
2367(3)
4171(3)
2711(3)
2898(3)
2765(5)
2930(5)
3400(5)
3718(5)
3561(5)
3071(5)
3126(6)
4097(7)
4747(7)
4428(9)
3471(8)
2804(6)
3909(1)
2269(1)
2317(1)
2081(3)
2339(3)
1524(3)
3446(3)
5508(5)
5850(5)
6906(5)
7609(5)
7272(6)
6221(5)
3091(5)
3623(6)
3146(9)
2166(10)
1608(7)
2069(6)
41(1)
37(1)
39(1)
42(1)
54(1)
55(1)
41(1)
41(2)
49(2)
58(2)
52(2)
61(2)
52(2)
47(2)
75(2)
99(3)
98(3)
86(3)
67(2)
O(1)
O(2)
O(3)
O(4)
C(11)
C(12)
C(13)
C(14)
C(43) –2341(5)
C(44) –2997(4)
C(45) –2333(4)
C(46)
–993(4)
Sb
S
6613.46(9) 9748.10(8) 7412.99(6) 37.89(2) C(15)
3940.4(4)
4916(1)
2970(1)
3183(2)
7966(2)
7609(2)
8526(2)
6278.6(4)
7494(1)
5949(1)
7120.9(3)
7479(1)
7798(1)
6118(1)
7286(1)
6474(1)
6333(2)
47.9(1)
52.0(3)
76.9(4)
82.3(5)
42.3(3)
51.6(4)
65.0(5)
C(16)
C(21)
C(22)
C(23)
C(24)
C(25)
C(26)
O(1)
O(2)
O(3)
C(11)
C(12)
C(13)
6203(1)
11490(1)
12108(2)
13189(2)
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 30 No. 1 2004

SYNTHESIS AND STRUCTURE
19
Table 3. (Contd.)
Atom
x
y
z
Ueq, Å2
Atom
x
y
z
Ueq, Å2
III
IV
C(31)
C(32)
C(33)
C(34)
C(35)
C(36)
C(41)
C(42)
C(43)
C(44)
C(45)
C(46)
C(51)
C(52)
C(53)
C(54)
C(55)
C(56)
C(61)
C(62)
C(63)
C(64)
C(65)
C(66)
C(71)
C(72)
C(73)
C(74)
C(75)
C(76)
C(81)
C(82)
C(83)
C(84)
C(85)
C(86)
687(5)
–57(6)
–968(7)
–1185(7)
–489(8)
468(6)
1219(5)
1415(6)
886(7)
185(8)
–36(7)
488(6)
3024(5)
4043(6)
4424(6)
3805(8)
2780(8)
2363(6)
861(5)
5870(2)
6157(3)
5932(4)
5449(4)
5170(3)
5376(3)
6856(2)
7340(3)
7731(3)
7635(3)
7153(3)
6771(2)
4196(2)
4344(2)
4355(2)
4212(2)
4070(3)
4066(2)
4101(2)
3870(2)
3888(2)
4131(2)
4347(2)
4346(2)
4029(2)
3592(2)
3561(3)
3967(3)
4396(3)
4433(2)
3241(2)
3014(3)
2507(3)
2207(3)
2409(3)
2923(3)
IV
3150(5)
2487(6)
1988(6)
2163(8)
2833(8)
3321(6)
4471(5)
4207(5)
4682(8)
5380(6)
5637(6)
5190(6)
3922(4)
4260(5)
5364(6)
6115(6)
5813(6)
4693(5)
1683(5)
2220(5)
1848(6)
867(6)
301(5)
719(5)
1028(4)
871(5)
66(6)
–605(5)
–468(5)
331(5)
2557(5)
3482(5)
3630(7)
2868(9)
1930(7)
1775(6)
44(2)
61(2)
82(2)
94(3)
93(3)
73(2)
46(2)
67(2)
86(3)
80(3)
85(3)
73(2)
39(2)
51(2)
64(2)
70(2)
80(2)
63(2)
38(2)
52(2)
62(2)
56(2)
60(2)
48(2)
37(2)
45(2)
59(2)
61(2)
59(2)
49(2)
44(2)
57(2)
75(2)
89(3)
89(3)
68(2)
C(21)
C(22)
C(23)
C(24)
C(25)
C(26)
C(31)
C(32)
C(33)
C(34)
4143(2)
4031(2)
3477(2)
3043(2)
3141(2)
3689(2)
5000
5544(3)
5531(4)
5000
3025(4)
3078(4)
2358(5)
1576(5)
1522(5)
2260(4)
6344(5)
7030(5)
8522(6)
9210(9)
V
1849(2)
1039(2)
617(2)
984(3)
1772(2)
2216(2)
2500
2926(3)
2923(5)
2500
38(1)
59(1)
74(2)
71(1)
65(1)
56(1)
55(2)
108(2)
154(3)
151(4)
Sb
S
O(1)
O(2)
O(3)
C(1)
5329.1(2)
6125.4(9)
6352(2)
5747(3)
7351(2)
4435(3)
3528(3)
1935(4)
1056(4)
1749(4)
3355(4)
4218(4)
3510(3)
1955(4)
824(4)
1237(4)
2762(4)
3902(4)
6991(3)
6698(4)
7840(4)
9235(4)
9518(4)
8407(4)
6342(4)
7955(4)
8580(5)
7618(5)
6047(5)
5397(5)
7388(4)
7750(4)
8119(5)
8127(5)
7765(6)
7395(5)
7073(8)
3780(30)
6250.8(2) 6495.4(1)
3234.9(7) 5988.0(5)
38.77(6)
41.6(2)
51.5(6)
58.8(7)
55.0(6)
37.4(8)
38.0(8)
47.8(9)
61(1)
67(1)
61(1)
52(1)
41(1)
52(1)
62(1)
64(1)
63(1)
58(1)
41(1)
53(1)
65(1)
3588(2)
1866(2)
3680(2)
4306(3)
3836(3)
3776(3)
3323(3)
2948(3)
2986(3)
3435(3)
7741(3)
7496(3)
8467(3)
9702(3)
9962(3)
8981(3)
7084(3)
8407(3)
9018(4)
8339(4)
7028(4)
6393(3)
6176(3)
5970(3)
5994(4)
6202(4)
6405(4)
6405(4)
925(4)
5124(1)
6155(1)
6494(1)
6295(2)
7033(2)
6977(2)
7644(2)
8373(2)
8434(2)
7762(2)
6705(2)
6652(2)
6854(2)
7106(2)
7144(2)
6956(2)
5697(2)
5393(2)
4933(2)
4770(2)
5060(2)
5524(2)
7674(2)
7766(2)
8536(2)
9217(3)
9132(2)
8363(2)
9092(2)
9162(3)
9926(3)
10619(3)
10549(2)
9786(3)
8284(4)
5784(16)
C(11)
C(12)
C(13)
C(14)
C(15)
C(16)
C(21)
C(22)
C(23)
C(24)
C(25)
C(26)
C(31)
C(32)
C(33)
C(34)
C(35)
C(36)
C(41)
C(42)
112(6)
–935(6)
–1282(5)
–549(6)
518(6)
3511(5)
4039(5)
4701(5)
4810(6)
4285(6)
3610(5)
2470(5)
2986(5)
2970(6)
2447(7)
1913(7)
1933(6)
62(1)
57(1)
50(1)
47(1)
61(1)
82(1)
93(2)
87(1)
Sb
S(1)
5000
4108.5(4)
4899(1)
4025(3)
6106(3)
5140(4)
3712(5)
2265(5)
1187(5)
–158(7)
–376(8)
617(8)
2500
37.2(1) C(43)
66.8(3) C(44)
51.9(7) C(45)
110(1)
113(1)
92(2)
77(2)
90(2)
122(2)
144(3)
143(3)
121(2)
4041(1)
4533(1)
4392(2)
3412(2)
3859(3)
3613(2)
4106(3)
3923(4)
3248(4)
2741(3)
2924(3)
3901(1)
3515(1)
4269(2)
3366(2)
4650(2)
4360(2)
4374(3)
4074(3)
3754(4)
3751(4)
4058(3)
O(1)
O(2)
O(3)
C(1)
C(11)
C(12)
C(13)
C(14)
C(15)
C(16)
C(46)
C(51)
C(52)
C(53)
C(54)
C(55)
C(56)
C(57)
H(1)
69(1)
170(3)
125(2)
181(3)
161(3)
249(5)
288(6)
187(3)
45
2258(4)
2724(4)
1856(6)
522(6)
57(4)
384(8)
2006(7)
4470(30)
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 30 No. 1 2004

20
SHARUTIN et al.
Table 4. Selected bond lengths and angles in structures I–V
Bond
d, Å
Angle
ω, deg
Bond
d, Å
Angle
ω, deg
I
III
1.504(4) O(1)SO(4)
1.440(4) C(61)Sb(2)C(51) 120.1(2)
1.442(4) C(51)Sb(2)C(71) 123.1(2)
1.511(4) C(61)Sb(2)C(71) 114.6(2)
Sb–C(41)
Sb–C(11)
Sb–C(31)
Sb–C(21)
S–O(2)
S–O(1)
S–O(3)
S–C(1)
C(1)–C(10)
C(1)–C(2)
C(2)–C(3)
C(3)–C(4)
C(4)–C(5)
C(4)–C(9)
C(5)–C(6)
C(6)–C(7)
C(7)–C(8)
C(8)–C(9)
C(9)–C(10)
2.100(4)
2.104(4)
2.114(4)
2.140(3)
1.381(3)
1.434(2)
1.459(4)
1.779(5)
1.352(5)
1.423(5)
1.350(5)
1.421(6)
1.419(6)
1.426(6)
1.373(7)
1.373(7)
1.372(6)
1.404(5)
1.410(5)
C(41)SbC(11)
C(41)SbC(31)
C(11)SbC(31)
C(41)SbC(21)
C(11)SbC(21)
C(31)SbC(21)
O(2)SO(1)
O(2)SO(3)
O(1)SO(3)
O(2)SC(1)
O(1)SC(1)
113.9(1) S–O(1)
113.6(2) S–O(2)
119.7(1) S–O(3)
106.7(1) S–O(4)
100.1(1)
106.4(2)
SO(1)Sb(2)
IV
138.3(2)
99.5(1)
113.2(3) Sb–C(21)
115.3(3) Sb–C(21)'
109.1(2) Sb–C(31)
106.2(2) Sb–O(1)'
105.6(2) Sb–O(1)
106.7(2) S(1)–O(3)
120.1(4) S(1)–O(2)
121.3(3) S(1)–O(1)
118.5(3) S(1)–C(1)
120.2(4) C(1)–C(11)
121.3(4) C(11)–C(16)
122.9(5) C(11)–C(12)
118.9(5) C(12)–C(13)
C(13)–C(14)
2.101(3) C(21)SbC(21)'
2.101(3) C(21)SbC(31)
2.102(5) C(21)'SbC(31)
2.111(2) C(21)SbO(1)'
2.111(2) C(21)'SbO(1)'
1.416(3) C(31)SbO(1)'
1.417(3) C(21)SbO(1)
1.496(3) C(21)'SbO(1)
1.792(5) C(31)SbO(1)
1.500(7) O(1)'SbO(1)
1.366(7) O(3)S(1)O(2)
1.387(7) O(3)S(1)O(1)
1.390(7) O(2)S(1)O(1)
1.343(9) O(3)S(1)C(1)
122.0(2)
119.0(1)
119.0(1)
86.7(1)
91.2(1)
92.12(7)
91.2(1)
O(3)SC(1)
C(10)C(1)C(2)
C(10)C(1)S
C(2)C(1)S
C(3)C(2)C(1)
C(2)C(3)C(4)
C(5)C(4)C(3)
C(5)C(4)C(9)
86.7(1)
92.12(7)
175.8(1)
117.2(2)
109.4(2)
110.5(2)
108.8(2)
108.1(2)
101.5(2)
138.3(2)
114.3(3)
II
Sb–C(31)
Sb–C(21)
Sb–C(41)
Sb–C(11)
Sb–O(1)
S–O(3)
S–O(2)
S–O(1)
S–C(50)
C(11)–C(16)
C(11)–C(12)
C(12)–C(13)
C(13)–C(14)
C(14)–C(15)
C(15)–C(16)
C(21)–C(26)
C(21)–C(22)
2.105(2)
2.105(2)
2.105(2)
2.131(2)
2.699(1)
1.442(2)
1.446(2)
1.453(1)
1.798(2)
1.383(2)
1.391(2)
1.385(2)
1.371(3)
1.366(3)
1.383(3)
1.378(2)
1.388(2)
C(31)SbC(21)
C(31)SbC(41)
C(21)SbC(41)
C(31)SbC(11)
C(21)SbC(11)
C(41)SbC(11)
C(31)SbO(1)
C(21)SbO(1)
C(41)SbO(1)
C(11)SbO(1)
O(3)SO(2)
O(3)SO(1)
O(2)SO(1)
O(3)SC(50)
O(2)SC(50)
O(1)SC(50)
SO(1)Sb
112.78(6) C(14)–C(15)
123.43(5) C(15)–C(16)
113.37(6) C(21)–C(26)
101.23(6) C(21)–C(22)
102.01(6)
1.35(1)
O(2)S(1)C(1)
1.432(9) O(1)S(1)C(1)
1.372(5) S(1)O(1)Sb
1.385(5) C(11)C(1)S(1)
V
99.38(6) Sb–C(31)
76.52(5) Sb–C(21)
80.71(5) Sb–C(41)
80.46(5) Sb–C(1)
177.04(5) Sb–O(3)
114.02(9) Sb–O(1)'
112.67(8) S–O(2)
111.73(8) S–O(1)
104.59(9) S–O(3)
107.00(9) S–C(1)
106.07(8) C(1)–C(11)
158.54(8) C(11)–C(16)
C(11)–C(12)
2.103(3) C(31)SbC(21)
2.111(3) C(31)SbC(41)
2.115(3) C(21)SbC(41)
2.166(3) C(31)SbC(1)
2.988(2) C(21)SbC(1)
3.019(2) C(41)SbC(1)
1.433(2) C(31)SbO(3)
1.446(2) C(21)SbO(3)
1.454(2) C(41)SbO(3)
1.816(3) C(1)SbO(3)
1.494(4) C(31)SbO(1)'
1.368(4) C(21)SbO(1)'
1.382(4) C(41)SbO(1)'
1.387(4) C(1)SbO(1)'
1.363(5) O(3)SbO(1)'
1.393(5) O(2)SO(1)
1.384(4) O(2)SO(3)
1.377(4) O(1)SO(3)
1.383(4) O(2)SC(1)
1.366(4) O(1)SC(1)
1.379(5) O(3)SC(1)
1.360(5) SO(3)Sb
108.7(1)
105.0(1)
98.7(1)
122.0(1)
111.4(1)
108.4(1)
87.07(9)
164.26(9)
77.06(9)
57.19(9)
78.50(9)
77.61(9)
175.66(9)
71.29(8)
105.92(6)
114.4(1)
114.7(1)
112.4(1)
106.7(1)
104.1(1)
103.1(1)
83.06(9)
104.8(1)
III
Sb(1)–C(31)
Sb(1)–C(11)
Sb(1)–C(21)
Sb(1)–C(41)
Sb(1)–O(4)
Sb(2)–C(51)
Sb(2)–C(81)
Sb(2)–C(61)
Sb(2)–C(71)
Sb(2)–O(1)
2.096(6)
2.118(6)
2.109(6)
2.178(6)
2.248(3)
2.101(6)
2.169(6)
2.095(6)
2.124(5)
2.271(3)
C(31)Sb(1)C(21) 124.9(3) C(12)–C(13)
C(21)Sb(1)C(11) 111.8(3) C(13)–C(14)
C(31)Sb(1)C(11) 121.6(2) C(14)–C(15)
C(41)Sb(1)O(4)
SO(4)Sb(1)
O(2)SO(3)
O(3)SO(1)
O(3)SO(4)
O(2)SO(1)
O(2)SO(4)
174.8(2) C(15)–C(16)
128.5(2) C(21)–C(26)
114.6(2) C(21)–C(22)
107.9(2) C(22)–C(23)
109.2(2) C(23)–C(24)
110.0(2) C(24)–C(25)
108.5(2) C(25)–C(26)
1.372(4) SC(1)Sb
Hydrogen bond parameters in crystal V
Distances, Å
H···O
Bond
Angle CHP, deg
128(2)
C–H
C···O
C(1)–H(1)···O(1)
1.02(3)
2.37(3)
3.100(3)
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 30 No. 1 2004

SYNTHESIS AND STRUCTURE
21
C(34)
C(33)
C(32)
C(31)
O(2)
O(3)
Sb
S(1)
O(1)
C(21)
C(26)
C(1)
C(11)
C(22)
C(23)
C(24)
C(12)
C(25)
C(16)
C(15)
C(13)
C(14)
Fig. 4. Structure of triphenylantimony bis(phenylmethanesulfonate) (IV).
O(2)
C(14)
C(13)
C(15)
C(12)
O(3)
O(1)
C(16)
S
H(1)
C(11)
C(1)
Sb'
C(43)
C(46)
C(44)
C(45)
C(42)
Sb
H(1)'
C(36)
O(1)'
C(41)
C(22)
O(3)'
C(31)
C(35)
S'
C(21)
C(23)
C(34)
C(32)
C(26)
O(2)'
C(24)
C(33)
C(25)
Fig. 5. Molecular structure of compound V.
Data collection and processing and refinement of grams [26].
the unit cell parameters were carried out using the
Selected crystallographic data and the results of
refinement of structures I–V are presented in Table 2,
coordinates of atoms are given in Table 3, and bond
SMART and SAINT-Plus programs [25]. All the cal-
culations for the structure determination and refine-
ment were performed using the SHELXTL/PC pro- lengths and angles are listed in Table 4.
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 30 No. 1 2004

22
SHARUTIN et al.
13. Sharutin, V.V., Sharutina, O.K., Molokova, O.V., et al.,
ACKNOWLEDGMENTS
Zh. Obshch. Khim., 2002, vol. 72, no. 6, p. 956.
The license to use the Cambridge Structural Data-
base was supported by the Russian Foundation for
Basic Research, project no. 99-07-90133.
14. Sharutin, V.V., Sharutina, O.K., Bondar’, E.A., et al.,
Koord. Khim., 2001, vol. 27, no. 6, p. 423.
15. Sharutin, V.V., Sharutina, O.K., Bondar’, E.A., et al.,
Koord. Khim., 2002, vol. 28, no. 5, p. 356.
16. Sharutin, V.V., Sharutina, O.K., Molokova, O.V., et al.,
Koord. Khim., 2002, vol. 28, no. 7, p. 497.
17. Sharutin, V.V., Sharutina, O.K., Molokova, O.V., et al.,
Koord. Khim., 2002, vol. 28, no. 8, p. 581.
18. Sharutin, V.V., Pakusina, A.P., and Senchurin, V.S.,
Trudy Vserossiiskogo Simpoziuma “Khimiya organ-
icheskikh soedinenii kremniya i sery” (Proc. All-Russian
Symp. “The Chemistry of Organic Compounds of Sili-
con and Sulfur), Irkutsk, 2001, p. 80.
19. Sharutin, V.V., Sharutina, O.K., Osipov, P.E., et al.,
Koord. Khim., 2001, vol. 27, no. 7, p. 518.
REFERENCES
1. Sharutin, V.V., Senchurin, V.S., Sharutina, O.K., et al.,
Zh. Obshch. Khim., 1996, vol. 66, no. 10, p. 1755.
2. Sharutin, V.V., Sharutina, O.K., Panova, L.P., and
Bel’skii, V.K., Zh. Obshch. Khim., 1997, vol. 67, no. 9,
p. 1531.
3. Sharutin, V.V., Sharutina, O.K., Pakusina, A.P., and
Bel’skii, V.K., Zh. Obshch. Khim., 1997, vol. 67, no. 9,
p. 1536.
4. Sharutin, V.V., Sharutina, O.K., Egorova, I.V., and
Panova, L.P., Zh. Obshch. Khim., 1998, vol. 68, no. 2,
p. 345.
20. Sharutin, V.V., Sharutina, O.K., Osipov, P.E., et al., Zh.
Obshch. Khim., 1997, vol. 67, no. 9, p. 1528.
21. Sharutin, V.V., Sharutina, O.K., Osipov, P.E., et al.,
Zhurn. Obshch. Khim., 2000, vol. 70, no. 6, p. 931.
5. Sharutin, V.V., Sharutina, O.K., Tarasova, T.A., et al., Zh.
Obshch. Khim., 2000, vol. 70, no. 8, p. 1979.
22. Sharutin, V.V., Zhidkov, V.V., Muslin, D.V., et al., Izv.
Ross. Akad. Nauk, Ser. Khim., 1995, no. 5, p. 958.
6. Sharutin, V.V., Sharutina, O.K., Tarasova, T.A., et al., Zh.
Obshch. Khim., 2000, vol. 70, no. 8, p. 1311.
23. Sharutin, V.V., Pakusina, A.P., Egorova, I.V., et al., Zh.
Obshch. Khim., 2003, vol. 73, no. 4, p. 569.
7. Sharutin, V.V., Fukin, G.K., Zakharov, L.N., et al., Zh.
Obshch. Khim., 2000, vol. 70, no. 12, p. 1997.
24. Sharutina, O.K., Doctoral (Chem.) Dissertation, Irkutsk:
Favorskii Inst. of Chemistry, Siberial Division, Russ.
Acad. Sci., 2001.
25. Ruther, H., Huber, F., and Preut, H., J. Organomet.
Chem., 1985, vol. 295, no. 1, p. 21.
26. SMART and SAINT-Plus. Versions 5.0. Data Collection
and Processing Software for the SMART System, Bruker
AXS Inc., Madison, WI, USA, 1998.
27. SHELXTL/PC. Versions 5.0. An Integrated System for
Solving, Refining, and Displaying Crystal Structures
From Diffraction Data, Bruker AXS Inc., Madison, WI,
USA, 1998.
8. Sharutin, V.V., Sharutina, O.K., Osipov, P.E., and Suba-
cheva, O.V., Zh. Obshch. Khim., 2001, vol. 71, no. 6,
p. 1045.
9. Sharutin, V.V., Sharutina, O.K., Molokova, O.V., et al.,
Zh. Obshch. Khim., 2001, vol. 71, no. 8, p. 1317.
10. Sharutin, V.V., Sharutina, O.K., Platonova, T.P., et al.,
Zh. Obshch. Khim., 2001, vol. 71, no. 10, p. 1637.
11. Sharutin, V.V., Sharutina, O.K., Panova, L.P., et al., Zh.
Obshch. Khim., 2002, vol. 72, no. 1, p. 45.
12. Sharutin, V.V., Sharutina, O.K., Bondar’, E.A., et al., Zh.
Obshch. Khim., 2002, vol. 72, no. 3, p. 419.
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