Synthesis and structure of tetraphenylantimony 2-furoinate and benzoate

Article abstract of DOI:10.1023/A:1021165112211

Tetraphenylantimony 2-furoinate Ph₄SbOC(O)C₄H ₃O is synthesized by the reaction of pentaphenylantimony with triphenylantimony bis(2-furoinate). The structure of the compound is determined by X-ray diffraction analysis. The Sb atom in the compound has a distorted trigonal-bipyramidal coordination with the phenyl and 2-furoinate groups in the axial positions. The Sb(1)-C(Ph)_eq distances lie in the 2.119(1)-2.121(1) A interval; the Sb-O(1) and Sb-C(Ph)_ax bond lengths are equal to 2.273(1) and 2.161(1) A, respectively; and the Sb(1)...O(2) intramolecular contact is 3.234(1) A.

Full text of DOI:10.1023/A:1021165112211

Russian Journal of Coordination Chemistry, Vol. 28, No. 11, 2002, pp. 753–757. Translated from Koordinatsionnaya Khimiya, Vol. 28, No. 11, 2002, pp. 803–808.
Original Russian Text Copyright © 2002 by Sharutin, Pakusina, Platonova, Egorova, Sharutina, A. Gerasimenko, Sergienko, E. Gerasimenko.
Synthesis and Structure of Tetraphenylantimony 2-Furoinate
and Benzoate
V. V. Sharutin, A. P. Pakusina, T. P. Platonova, I. V. Egorova, O. K. Sharutina,
A. V. Gerasimenko, A. S. Sergienko, and E. A. Gerasimenko
Blagoveshchensk State Pedagogical University, ul. Lenina 104, Blagoveshchensk, 675000 Russia
Institute of Chemistry, Far East Division, Russian Academy of Sciences,
pr. Stoletiya Vladivostoka 159, Vladivostok, 690022 Russia
Received May 25, 2001
Abstract—Tetraphenylantimony 2-furoinate Ph4SbOC(O)C4H3O is synthesized by the reaction of pentaphenyl-
antimony with triphenylantimony bis(2-furoinate). The structure of the compound is determined by X-ray dif-
fraction analysis. The Sb atom in the compound has a distorted trigonal-bipyramidal coordination with the phe-
nyl and 2-furoinate groups in the axial positions. The Sb(1)–C(Ph)eq distances lie in the 2.119(1)–2.121(1) Å
interval; the Sb–O(1) and Sb–C(Ph)ax bond lengths are equal to 2.273(1) and 2.161(1) Å, respectively; and the
Sb(1)···é(2) intramolecular contact is 3.234(1) Å.
INTRODUCTION
Tetraphenylantimony benzoate was synthesized
similarly.
In the majority of antimony compounds with the
general formula Ar4Sbï (X is an organic or inorganic
X-ray diffraction analysis of crystals I and II was
ligand), the Sb atom has the trigonal bipyramid config- performed on a SMART-1000 CCD automated diffrac-
uration with coordination number (CN) 5 [1]. However, tometer (Bruker). The data for compound I were col-
when the ligands contain potential coordination sites, lected in sets of 606, 435, and 230 frames at the angle
they can additionally interact with the Sb atom. As a ϕ = 0°, 90°, and 180°, respectively (ω scan mode with an
result, a coordination environment of the Sb atom with increment of 0.3° and exposure of 10 s per frame for
CN 6 can be realized. For example, most tetraarylanti- compound I and 20 s per frame for compound II).
mony acylates [2–8] exhibit shortened Sb···O distances
The structures were determined by the direct
as compared to the sum of van der Waals radii, thus
method and refined by the least-squares method in the
indicating an additional coordination of the Sb atom in
anisotropic approximation for all non-hydrogen atoms.
these compounds.
The positions of hydrogen atoms were calculated geo-
In continuation of our studies on the structures of
tetraphenylantimony acylates [2–8], we examined the
molecular and crystal structures of tetraphenylanti-
mony 2-furoinate (I) and tetraphenylantimony ben-
zoate (II), which are antimony derivatives that differ
only in the nature of the arene ring of the carboxylic
acid. The structure of compound II determined with
lower accuracy than in the present work, was reported
in [8].
metrically and included in the refinement by the “rider”
model.
The data collection and editing and the refinement
of the unit cell parameters were performed using the
SMART and SAINT-Plus program packages [9]. All
calculations for determination and refinement of the
structures were performed using the SHELXTL/PC
program package [10].
The main crystallographic data and results of refine-
ment of the structures are presented in Table 1. The
1
EXPERIMENTAL
atomic coordinates are presented in Table 2, and the
bond lengths and angles are given in Table 3.
Synthesis of tetraphenylantimony 2-furoinate was
carried out in an evacuated glass tube as follows. Pen-
taphenylantimony (1.00 g, 1.97 mmol) and triphenylan-
timony bis(2-furoinate) (1.13 g, 1.96 mmol) in toluene
(10 ml) were heated at 90°ë for 1 h. The solvent was
removed, and the residue was recrystallized from a ben-
zene–heptane (3 : 1) mixture. The complex was
obtained in 96% yield (2.05 g), mp 166°C.
RESULTS AND DISCUSSION
Compounds I and II were synthesized by the dispro-
portionation of pentaphenylantimony and triphenylan-
timony diacylates in toluene at 90°ë. The reaction was
IR (ν, cm–1): 1630 vs, 1395 vs, 1180 vs, 1125 s,
1060 vs.
1
The coordinates of hydrogen atoms and their thermal isotropic
parameters can be made available by the authors.
1070-3284/02/2811-0753$27.00 © 2002 åÄIä “Nauka /Interperiodica”

754
SHARUTIN et al.
Table 1. Summary of data collection and refinement of structures I and II
Parameter
Empirical formula
I
II
C29H23O3Sb
C31H25O2Sb
551.26
Molecular weight
Temperature, K
Wavelength
541.22
293(2)
295(2)
MoKα (0.71073 Å)
MoKα (0.71073 Å)
P21/n
Space group
P21/c
a, Å
9.863(1)
10.395(1)
14.643(2)
17.199(2)
103.508(2)
2545.6(6)
4
b, Å
14.867(2)
c, Å
17.102(2)
β, deg
V, Å3
105.286(2)
2414.0(5)
Z
4
ρ(calcd), g/cm3
µ, mm–1
1.489
1.438
1.171
1088
1.109
F(000)
1112
Crystal shape
Prism (0.20 × 0.20 × 0.27 mm)
2.14–30.05
Prism (0.2 × 0.26 × 0.4 mm)
1.85–30.01
Range of θ, deg
Intervals of refractive indices
Measured reflections
Independent reflections
Reflections with I > 2σ(I)
Refinement method
Refinement variables
GOOF
–13 ≤ h ≤ 13, –13 ≤ k ≤ 20, –24 ≤ l ≤ 21 –14 ≤ h ≤ 14, –15 ≤ k ≤ 20, –21 ≤ l ≤ 24
18252
7004 (Rint = 0.0370)
4913
19119
7402 (Rint = 0.0378)
4829
Full-matrix least-squares for F2
Full-matrix least-squares for F2
299
307
0.905
0.884
R factors for F2 > 2σ(F2)
R factors for all reflections
Molar absorption coefficient
Residual electron density (min/max), e/Å3
R1 = 0.0264, wR2 = 0.0555
R1 = 0.0454, wR2 = 0.0602
0.00096(8)
R1 = 0.029, wR2 = 0.056
R1 = 0.0561, wR2 = 0.0633
Was not applied
–0.336/0.323 (near Sb atom)
–0.454/0.558 (near Sb atom)
almost complete after 1-h heating of the reaction mix- of the furan fragment as compared to that of the phenyl
ture.
Ph5Sb + Ph3Sb[OC(O)R]2
(R = C4H3O, C6H5).
substituent. The C(1)–C(2) bond in I equal to 1.482(2) Å
is much shorter than the analogous bond in II
(1.507(2) Å), indicating that the  electrons of the car-
bonyl carbon atom are involved to a greater extent in
the conjugation with the π-system of the furan ring in
compound I than in compound II. The angles between
the planes of the arene ring and carboxyl groups in the
carboxylate fragment (16.12° and 30.58° in I and II,
respectively) also confirm this fact.
2Ph4SbOC(O)R
X-ray diffraction analysis of compounds I and II
showed that the Sb atoms have a distorted trigonal-
bipyramidal coordination (Figs. 1, 2) with the O atoms
of the carboxylate ligands in the axial positions. The
sums of the C(Ph)SbC(Ph) angles in the equatorial
plane are 356.56(5)° and 356.17(6)°, and the axial
angles O(1)SbC(11) in I and O(1)SbC(21) in II are
176.46(4)° and 176.66(5)°, respectively. The
C(Ph)SbC(Ph) angles between the equatorial phenyl
ligands are different: 130.75(5)°, 116.55(5)°, and
109.26(5)° in I and 129.14(6)°, 115.28(5)°, and
111.75(6)° in II.
The Sb···O(2) distances, which are equal to 3.234(1)
and 3.305(1) Å for compounds I and II, respectively,
are much shorter than the sum of the van der Waals radii
of the Sb and O atoms (3.7 Å [11]), and the longer Sb–
O(1) bond corresponds to the shorter Sb···O(2) contact
in I. As in other tetraarylantimony acylates [2–8], the
value of the angles on the side of the intramolecular
The Sb–O(1) bond length in compound I (2.273(1) Å) Sb···O(2) contacts in I and II exceeds the standard value
is much longer than that in II (2.245(1) Å), which can of 120°. Thus, the coordination number of the Sb atom
be explained by the higher electron-withdrawing ability in compounds I and II is 6 (5 + 1).
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 28 No. 11 2002

SYNTHESIS AND STRUCTURE OF TETRAPHENYLANTIMONY 2-FUROINATE
755
Table 2. Atomic coordinates (×104) and equivalent isotropic thermal parameters (×103) in structures I and II
Atom
x
y
z
Ueq, Å2 Atom
x
y
z
Ueq, Å2
I
II
4621.93(9) 5241.31(7) 2017.77(6) 41.66(3)
Sb
2502.73(9) 9847.80(6) 1930.98(5) 36.99(2) Sb
O(1)
O(2)
O(3)
C(1)
C(2)
C(3)
C(4)
C(5)
C(11)
C(12)
4652(1)
5655(1)
8081(1)
5695(1)
7009(2)
7384(2)
8775(2)
9150(2)
518(1)
9182.3(7)
10342.3(7)
9323(1)
2196.6(6) 49.8(3)
2972.8(7) 57.2(3)
3505.0(7) 82.5(4)
O(1)
O(2)
C(1)
2864.4(9) 5925.7(7) 2315.7(6)
2439.5(11) 4801.4(8) 3090.6(7)
2163.2(14) 5523.2(11) 2738.4(9)
908.1(13) 6025.6(11) 2762.5(9)
52.1(3)
63.1(3)
45.6(4)
48.2(4)
9599(1)
2682(1)
2866(1)
2499(1)
2914(1)
3517(1)
1660(1)
2167(1)
1981(1)
1282(1)
775(1)
44.3(4)
51.0(4)
57.4(5)
88.4(7)
92.8(7)
38.3(3)
52.4(4)
56.7(4)
54.5(4)
53.4(4)
45.1(4)
39.7(3)
49.9(4)
60.2(5)
60.2(5)
64.1(5)
57.6(5)
41.3(4)
55.3(4)
68.6(6)
71.7(6)
75.7(6)
61.9(5)
38.6(3)
49.5(4)
62.0(5)
62.6(5)
57.2(5)
49.4(4)
C(11)
C(12)
9063(1)
369.9(15) 5949.5(13) 3426.3(10) 64.9(5)
8350(1)
C(13) –790.7(17) 6429.3(16) 3443.7(12) 85.1(7)
C(14) –1408.9(17) 6936.0(15) 2797.2(14) 88.6(7)
C(15) –891.8(17) 6997.2(14) 2136.6(13) 79.1(7)
8131(1)
8701(2)
10556(1)
10499(1)
10932(1)
11434(1)
11505(1)
11071(1)
9845(1)
C(16)
274.7(16) 6555.6(12) 2122.7(11) 60.7(5)
–375(2)
C(21) 6241.0(14) 4524.6(10) 1687.0(9)
C(22) 6023.3(14) 3992.5(11) 1002.8(8)
C(23) 7051.9(15) 3565.7(12) 764.0(9)
43.8(4)
48.9(4)
56.2(5)
C(13) –1654(2)
C(14) –2068(2)
C(15) –1205(2)
C(24) 8313.1(15) 3668.3(12) 1204.7(10) 60.2(5)
C(25) 8567.6(15) 4190.8(13) 1890.1(11) 63.3(5)
C(26) 7531.7(15) 4611.0(11) 2131.6(11) 57.7(5)
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)
71(2)
2836(1)
3047(2)
3207(2)
3146(2)
2918(2)
2755(2)
3356(1)
3739(2)
4123(2)
4134(2)
3757(2)
3365(2)
1759(1)
329(2)
960(1)
3207(1)
3610(1)
4437(1)
4861(1)
4457(1)
3634(1)
1173(1)
1381(1)
832(1)
9038(1)
C(31) 5451.9(13) 5262.2(11) 3264.8(9)
46.2(4)
9005(1)
C(32) 5929.6(19) 4487.0(13) 3669.3(10) 70.7(6)
C(33) 6490.7(19) 4512.4(15) 4482.6(11) 79.7(7)
C(34) 6628.0(17) 5324.2(14) 4889.1(10) 68.4(6)
C(35) 6184.7(17) 6106.3(14) 4475.7(10) 69.9(6)
9776(1)
10582(1)
10629(1)
10680(1)
11559(1)
12121(1)
11811(1)
10947(1)
10372(1)
8563(1)
C(36) 5589.8(15) 6077.6(12) 3667.2(9)
C(41) 3128.3(12) 4376.2(11) 1348.9(8)
57.3(5)
42.4(4)
C(42) 2345.5(17) 4699.8(13) 643.1(11) 63.6(5)
C(43) 1440.4(17) 4135.5(15) 159.5(11) 74.7(6)
C(44) 1297.5(15) 3252.8(14) 372.0(11) 66.6(6)
C(45) 2062.8(16) 2926.0(13) 1072.8(12) 70.8(6)
C(46) 2986.7(15) 3482.3(13) 1561.1(10) 61.2(5)
88(1)
–129(1)
414(1)
1464(1)
1149(1)
873(1)
8450(1)
C(51) 4835.3(13) 6520.5(10) 1478.0(8)
C(52) 4151.3(15) 7299.9(11) 1607.8(9)
40.9(4)
53.3(4)
–223(2)
657(2)
7612(1)
6886(1)
914(1)
C(53) 4358.9(16) 8123.2(12) 1273.1(10) 61.7(5)
C(54) 5237.2(16) 8183.5(12) 791.9(10) 62.2(5)
C(55) 5911.1(15) 7421.2(13) 653.0(10) 61.2(5)
2077(2)
2641(2)
6987(1)
1229(1)
1500(1)
7826(1)
C(56) 5729.8(14) 6589.2(11) 995.6(9)
48.7(4)
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 28 No. 11 2002

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SHARUTIN et al.
Table 3. Interatomic distances and bond angles in structures I and II
I
II
Bond
d, Å
Angle
ω, deg
Bond
d, Å
Angle
ω, deg
Sb–C(31)
Sb–C(21)
Sb–C(41)
Sb–C(11)
Sb–O(1)
2.119(1) C(31)SbC(21)
2.120(1) C(31)SbC(41)
2.121(1) C(21)SbC(41)
2.161(1) C(31)SbC(11)
2.273(1) C(21)SbC(11)
3.234(1) C(41)SbC(11)
1.295(2) C(31)SbO(1)
1.215(2) C(21)SbO(1)
1.361(2) C(41)SbO(1)
1.398(2) C(11)SbO(1)
1.482(2) C(2)O(3)C(5)
1.332(2) O(2)C(1)O(1)
1.407(2) O(2)C(1)C(2)
1.309(3) O(1)C(1)C(2)
130.75(5) Sb–C(31)
116.55(5) Sb–C(41)
109.26(5) Sb–C(51)
93.96(5) Sb–C(21)
96.19(5) Sb–O(1)
2.117(2) C(31)SbC(41)
2.122(1) C(31)SbC(51)
2.125(2) C(41)SbC(51)
2.169(2) C(31)SbC(21)
2.245(1) C(41)SbC(21)
3.305(1) C(51)SbC(21)
1.286(2) C(31)SbO(1)
1.219(2) C(41)SbO(1)
1.507(2) C(51)SbO(1)
1.381(2) C(21)SbO(1)
1.388(2) C(31)SbO(2)
1.403(2) C(41)SbO(2)
1.366(3) C(51)SbO(2)
1.369(3) C(21)SbO(2)
1.379(3) O(1)SbO(2)
1.385(2) O(2)C(1)O(1)
1.386(2) O(2)C(1)C(11)
1.381(2) O(1)C(1)C(11)
1.361(2) C(16)C(11)C(12)
1.378(2) C(16)C(11)C(1)
1.386(2) C(12)C(11)C(1)
1.363(2) C(11)C(12)C(13)
1.371(2) C(14)C(13)C(12)
1.385(2) C(13)C(14)C(15)
1.369(3) C(14)C(15)C(16)
1.370(3) C(15)C(16)C(11)
1.384(2) C(22)C(21)C(26)
1.376(2) C(23)C(22)C(21)
1.378(2) C(24)C(23)C(22)
1.376(2) C(23)C(24)C(25)
1.361(3) C(24)C(25)C(26)
1.366(2) C(25)C(26)C(21)
1.384(2) C(32)C(31)C(36)
1.387(2) C(31)C(32)C(33)
1.390(2) C(34)C(33)C(32)
1.375(2) C(33)C(34)C(35)
1.371(2) C(34)C(35)C(36)
1.368(2) C(31)C(36)C(35)
1.385(2) C(46)C(41)C(42)
C(43)C(42)C(41)
129.14(6)
111.75(6)
115.28(5)
96.61(6)
94.78(5)
98.36(6)
85.59(5)
81.89(5)
83.10(5)
176.66(5)
66.90(4)
71.07(4)
124.82(4)
136.72(5)
42.13(3)
125.41(1)
121.0(1)
113.6(1)
119.4(2)
120.5(1)
120.1(1)
119.4(2)
119.9(2)
120.7(2)
120.1(2)
120.5(2)
117.7(1)
121.5(1)
119.8(2)
120.4(2)
119.7(1)
120.9(2)
119.0(2)
120.7(2)
120.5(2)
118.6(2)
120.9(2)
120.2(2)
118.9(1)
120.4(2)
120.7(2)
119.5(2)
120.5(2)
120.1(2)
118.4(1)
121.1(2)
120.1(2)
119.6(2)
121.2(2)
119.7(2)
Sb–O(2)
98.73(5) Sb–O(2)
O(1)–C(1)
O(2)–C(1)
O(3)–C(2)
O(3)–C(5)
C(1)–C(2)
C(2)–C(3)
C(3)–C(4)
C(4)–C(5)
82.84(4) O(1)–C(1)
84.84(4) O(2)–C(1)
84.08(4) C(1)–C(11)
176.46(4) C(11)–C(16)
104.3(2)
126.2(1)
121.4(1)
112.5(1)
110.6(1)
131.4(1)
118.0(1)
107.4(2)
106.5(2)
111.1(2)
117.4(1)
121.4(1)
119.8(2)
120.1(1)
120.1(1)
121.3(1)
119.5(1)
120.4(1)
120.4(2)
119.2(2)
121.3(2)
119.3(2)
119.2(2)
120.1(2)
120.3(2)
120.5(2)
120.0(2)
119.9(2)
119.0(1)
120.7(1)
120.0(2)
120.0(2)
120.5(2)
120.0(1)
C(11)–C(12)
C(12)–C(13)
C(13)–C(14)
C(14)–C(15)
C(15)–C(16)
C(21)–C(22)
C(21)–C(26)
C(22)–C(23)
C(23)–C(24)
C(24)–C(25)
C(25)–C(26)
C(31)–C(32)
C(31)–C(36)
C(32)–C(33)
C(33)–C(34)
C(34)–C(35)
C(35)–C(36)
C(41)–C(46)
C(41)–C(42)
C(42)–C(43)
C(43)–C(44)
C(44)–C(45)
C(45)–C(46)
C(51)–C(56)
C(51)–C(52)
C(52)–C(53)
C(53)–C(54)
C(54)–C(55)
C(55)–C(56)
C(11)–C(16) 1.390(2) C(3)C(2)O(3)
C(11)–C(12) 1.392(2) C(3)C(2)C(1)
C(12)–C(13) 1.376(2) O(3)C(2)C(1)
C(13)–C(14) 1.377(2) C(2)C(3)C(4)
C(14)–C(15) 1.369(2) C(5)C(4)C(3)
C(15)–C(16) 1.375(2) C(4)C(5)O(3)
C(21)–C(22) 1.369(2) C(16)C(11)C(12)
C(21)–C(26) 1.386(2) C(13)C(12)C(11)
C(22)–C(23) 1.383(2) C(12)C(13)C(14)
C(23)–C(24) 1.365(2) C(15)C(14)C(13)
C(24)–C(25) 1.371(2) C(14)C(15)C(16)
C(25)–C(26) 1.375(2) C(15)C(16)C(11)
C(31)–C(36) 1.377(2) C(22)C(21)C(26)
C(31)–C(32) 1.379(2) C(21)C(22)C(23)
C(32)–C(33) 1.381(2) C(24)C(23)C(22)
C(33)–C(34) 1.356(3) C(23)C(24)C(25)
C(34)–C(35) 1.359(3) C(24)C(25)C(26)
C(35)–C(36) 1.389(3) C(25)C(26)C(21)
C(41)–C(42) 1.381(2) C(36)C(31)C(32)
C(41)–C(46) 1.389(2) C(31)C(32)C(33)
C(42)–C(43) 1.388(2) C(34)C(33)C(32)
C(43)–C(44) 1.374(2) C(33)C(34)C(35)
C(44)–C(45) 1.370(2) C(34)C(35)C(36)
C(45)–C(46) 1.392(2) C(31)C(36)C(35)
C(42)C(41)C(46)
C(41)C(42)C(43)
C(44)C(43)C(42)
C(45)C(44)C(43)
C(44)C(45)C(46)
C(44)C(43)C(42)
C(43)C(44)C(45)
C(44)C(45)C(46)
C(41)C(46)C(45)
C(56)C(51)C(52)
C(53)C(52)C(51)
C(54)C(53)C(52)
C(55)C(54)C(53)
C(41)C(46)C(45)
C(54)C(55)C(56)
C(55)C(56)C(51)
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 28 No. 11 2002

SYNTHESIS AND STRUCTURE OF TETRAPHENYLANTIMONY 2-FUROINATE
757
C(33)
C(32)
C(25)
C(14)
C(15)
C(16)
C(34)
C(35)
C(31)
C(26)
C(13)
C(12)
O(2)
C(21)
C(11)
C(24)
C(36)
O(1)
Sb
O(3)
C(1)
C(23)
C(5)
C(4)
C(22)
C(2)
C(42)
C(43)
C(41)
C(46)
C(45)
C(3)
C(44)
Fig. 1. Molecular structure of tetraphenylantimony 2-furoinate (I).
ACKNOWLEDGMENTS
This work was supported by the Russian Foundation
for Basic Research, project no. 99-07-90133.
C(14)
C(13)
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C(15)
C(16)
C(12)
C(43)
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C(44)
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C(11)
C(1)
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C(42)
O(2)
C(45)
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C(46)
O(1)
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C(41)
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C(52)
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C(51)
C(53)
C(54)
C(55)
C(56)
Sb
C(21)
C(22)
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C(32)
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C(31)
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C(36)
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C(23)
C(33)
9. SMART and SAINT-Plus, Versions 5.0.: Data Collection
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10. Sheldrick, G.M., SHELXTL/PC, Versions 5.10: An Inte-
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C(35)
C(34)
C(24)
C(25)
Fig. 2. Molecular structure of tetraphenylantimony ben-
zoate (II).
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RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 28 No. 11 2002