Synthesis and structures of tetra-and triarylantimony oximates

Article abstract of DOI:10.1023/A:1019701511840

Tetraphenylantimony acetophenoneoximate (I) and tetra-n-tolylantimony 3-nitrobenzaloximate (II) were synthesized by reacting pentaarylantimony with oxime or triarylantimony dioximate in toluene. Tri-n-tolylantimony bis(acetophenoneoximate) (III) and triphenylantimony bis(cyclohexanoneoximate) (IV) were synthesized by reacting triarylantimony with oxime and hydrogen peroxide. The structures of compounds I-IV were determined using X-ray diffraction analysis. The antimony atoms in I-IV are coordinated to the axial oxime groups to form a distorted trigonal bipyramid. The Sb-C(Ph) and Sb-O bond lengths and Sb...N intramolecular contacts in structures I and II lie within 2.114-2.135, 2.137-2.154, and 2.857-2.871 A, respectively; the respective values in structures III and IV are 2.097-2.112, 2.058-2.080, and 2.779-2.874 A.

Full text of DOI:10.1023/A:1019701511840

Russian Journal of Coordination Chemistry, Vol. 28, No. 8, 2002, pp. 544–553. Translated from Koordinatsionnaya Khimiya, Vol. 28, No. 8, 2002, pp. 581–590.
Original Russian Text Copyright © 2002 by Sharutin, Sharutina, Molokova, Pakusina, Gerasimenko, Sergienko, Bukvetskii, Popov.
Synthesis and Structures of Tetra-
and Triarylantimony Oximates
V. V. Sharutin, O. K. Sharutina, O. V. Molokova, A. P. Pakusina, A. V. Gerasimenko,
A. S. Sergienko, B. V. Bukvetskii, and D. Yu. Popov
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 acetophenoneoximate (I) and tetra-n-tolylantimony 3-nitrobenzaloximate
(II) were synthesized by reacting pentaarylantimony with oxime or triarylantimony dioximate in toluene. Tri-
n-tolylantimony bis(acetophenoneoximate) (III) and triphenylantimony bis(cyclohexanoneoximate) (IV) were
synthesized by reacting triarylantimony with oxime and hydrogen peroxide. The structures of compounds I–IV
were determined using X-ray diffraction analysis. The antimony atoms in I–IV are coordinated to the axial
...
oxime groups to form a distorted trigonal bipyramid. The Sb–C(Ph) and Sb–O bond lengths and Sb N intramo-
lecular contacts in structures I and II lie within 2.114–2.135, 2.137–2.154, and 2.857–2.871 Å, respectively;
the respective values in structures III and IV are 2.097–2.112, 2.058–2.080, and 2.779–2.874 Å.
According to the valence shell electron pair repul- oximate (II), tri-n-tolylantimony bis(acetophenoneoxi-
sion theory (VSEPR), molecules whose central atoms mate) (III), and triphenylantimony bis(cyclohexanone-
contain five electron pairs on the valence shell prefera- oximate) (IV).
bly have trigonal-bipyramidal configuration with the
axial ligands more removed father from the centre than
the equatorial ligands [1]. In terms of the VSEPR the-
EXPERIMENTAL
ory, electronegative substituents in these molecules
always occupy the axial positions. The higher the elec-
tronegativity of the ligand, the more remote it is from
the central atom [2]. Molecules of organic antimony
compounds with the general formulas Ar4SbX and
Ar3SbX2 (X is the electronegative ligand) usually have
the form of a trigonal bipyramid with axial substituents
X [3], which agrees with the VSEPR theory. However,
some of the structurally characterized antimony(V)
compounds are beyond the framework of this theory.
Thus, in dimethoxytriphenylantimony, the axial (ax)
Sb–O bonds are shorter than the equatorial (eq) Sb–C
bonds [4]. Furthermore, in methoxytetraphenylanti-
mony [4], aroxytetraarylantimony compounds contain-
ing electron-donating substutuents in the aroxy group
[5–7] and in tetraphenylantimony oximates [8, 9], the
Sb–Oax bonds are shorter than the Sb–Cax bonds. This
contradicts the rule asserting that the distance between
the ligand and the central atom increases with increas-
ing electronegativity of the ligand. If ligand X contains
potential coordination centers, then, similar to tetra-
and triarylantimony acylates [10–17], trigonal-bipyra-
midal coordination of the Sb atom can be distorted and
its coordination number can increase to six or seven.
Synthesis of tetraphenylantimony acetophenone-
oximate (I). A mixture of 1.00 g (1.97 mmol) of Ph5Sb
and 0.27 g (1.97 mmol) of HON=CMePh in 10 ml of
toluene was heated at 90°ë for 1 h. After cooling, the
solvent was removed; the residue was recrystallized
from a toluene–heptane mixture (1 : 3). The yield was
1.05 g (94%), mp 126°C. Compound I was also
obtained from Ph5Sb and Ph3Sb(ON=CMePh)2 in a
yield of 95% (toluene, 90°ë, 1 h).
Tetra-n-tolylantimony 3-nitrobenzaloximate (II)
was synthesized similar to I. The yield was 99%, mp
129°C.
Synthesis of tri-n-tolylantimony bis(acetophe-
noneoximate) (III). A solution of 1.00 g (2.53 mmol)
of tri-n-tolylstibine and 0.69 g (5.03 mmol) of ace-
tophenoneoxime in 20 ml of ether was mixed with
0.29 ml of 30% aqueous hydrogen peroxide. The mix-
ture was allowed to stand at 20°ë for 12 h. The color-
less crystals that formed were filtered off and dried. The
yield was 1.59 g (95%), mp 126°C.
Triphenylantimony bis(cyclohexanoneoximate)
(IV) was synthesized similar to III. The yield was 92%,
mp = 124°C (116°C [18]).
With the purpose of studying the structures of aryl
X-ray diffraction analysis of the natural-faceted
Sb(V) compounds in more detail, we carried out X-ray single crystals of I–IV was carried out on a Bruker
diffraction analysis of tetraphenylantimony acetophe- SMART-1000 CCD diffractometer. For compound I,
noneoximate (I), tetra-n-tolylantimony 3-nitrobenzal- the data were collected in sets of 606 frames at ϕ = 0°,
1070-3284/02/2808-0544$27.00 © 2002 åÄIä “Nauka /Interperiodica”

SYNTHESIS AND STRUCTURES OF TETRA- AND TRIARYLANTIMONY OXIMATES
545
Table 1. Crystallographic data and details of data collection for structures I–IV
Value
Parameter
I
II
III
IV
Empirical formula
C67H59N2O2Sb2
1167.66
C35H33N2O3Sb
651.38
C37H37N2O2Sb
663.44
C30H35N2O2Sb
577.35
M
T, K
296(2)
296(2)
293(2)
295(2)
Radiation (λ, Å)
MoKα (0.71073)
MoKα (0.71073)
MoKα (0.71073)
MoKα (0.71073)
P21/n
Space group
P21/c
P1
P1
Unit cell parameters:
a, Å
13.759(2)
13.855(2)
17.956(2)
72.260(2)
72.627(2)
62.443(2)
2839.4(6)
2
10.5225(11)
15.9662(17)
19.027(2)
90
11.925(1)
14.806(1)
19.809(2)
101.922(2)
99.797(2)
95.974(2)
3336.6(6)
4
10.176(1)
15.222(2)
17.839(2)
90
b, Å
c, Å
α, deg
β, deg
93.847(2)
90
95.716(3)
90
γ, deg
V, Å3
3189.3(6)
4
2749.4(7)
4
Z
ρ (calcd), g/cm3
µMo, mm–1
1.366
1.357
1.321
1.395
0.997
0.900
0.860
1.032
F(000)
1186
1328
1360
1184
Crystal shape and size, mm
Prism
0.20 × 0.23 × 0.33
Prism
0.12 × 0.19 × 0.33
Prism
0.20 × 0.23 × 0.25
Prism
0.06 × 0.10 × 0.20
θ, deg
1.89–30.03
2.50–23.28
1.97–26.10
2.41–28.01
Range of indices
–19 ≤ h ≤ 19,
–19 ≤ k ≤ 19,
–25 ≤ l ≤ 25
–9 ≤ h ≤ 11,
–16 ≤ k ≤ 17,
–21 ≤ l ≤ 21
–14 ≤ h ≤ 14,
–18 ≤ k ≤ 18,
–24 ≤ l ≤ 24
–13 ≤ h ≤ 13,
–16 ≤ k ≤ 20,
–23 ≤ l ≤ 19
Total number of reflections
Independent reflections
Reflections with I > 2σ(I)
41560
13309
36938
18013
16370 (Rint = 0.0410) 4597 (Rint = 0.0369) 13192 (Rint = 0.0520) 6611 (Rint = 0.0547)
10473
661
3581
374
7655
767
4087
317
Number of refined parame-
ters
GOOF
0.926
0.940
0.824
0.829
Final R-factor (I > 2σ(I))
R1 = 0.0294,
wR2 = 0.0671
R1 = 0.0272,
wR2 = 0.0620
R1 = 0.0356,
wR2 = 0.0701
R1 = 0.0333,
wR2 = 0.0637
90°, 180°, and 270°; for compounds II–IV, sets of 606, IV were calculated and refined using the
435, and 230 frames were collected at ϕ = 0°, 90°, and SHELXTL/PC programs [20].
180° (ω-scan with an angle of 0.3° between the frames
Selected crystallographic parameters and the details
and 10 s exposition per frame (for compound IV, 20 s
of refinement of structures I–IV are presented in Table 1,
per frame); the crystal–detector distance was 45 mm).
coordinates and thermal parameters of atoms are given
Correction for absorption of X-rays by the samples was
in Table 2, and their bond lengths and angles are listed
applied using face indices.
in Table 3.
The structures of compounds I–IV were solved by
the direct methods and refined by the least-squares
method in anisotropic approximation for non-hydrogen
atoms. Positions of hydrogen atoms were calculated
geometrically and refined in the rider model.
RESULTS AND DISCUSSION
Compounds I and II were synthesized from pen-
taarylantimony and oxime or triarylantimony dioxi-
mate:
Data collection and processing and refinement of
the unit cell parameters were performed using the
SMART and SAINT Plus programs [19]. Structures I–
Ar5Sb + HON=CRR'
Ar4SbON=CRR' + ArH,
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 28 No. 8 2002

546
SHARUTIN et al.
Table 2. Coordinates of atoms (×104) and their equivalent isotropic thermal parameters (×103) in structures I–IV
Atom
x
y
z
Ueq, Å2
Atom
x
y
z
Ueq, Å2
I
I
Sb(1)
5183.52(7) 2225.32(8) 2447.49(6) 43.57(3) C(61)
958.80(7) 7986.68(8) 3091.41(6) 44.88(3) C(62)
561(1)
9738(1) 2495(1)
47.9(4)
61.4(5)
79.4(6)
83.1(6)
76.6(6)
62.3(5)
46.9(4)
59.4(5)
74.3(5)
77.7(6)
78.7(6)
65.1(5)
51.1(4)
81.1(6)
95.1(7)
82.8(7)
77.1(6)
61.7(5)
46.3(4)
56.8(5)
70.9(5)
78.1(5)
77.5(6)
62.7(5)
54.4(5)
65.9(6)
81.8(8)
90.5(8)
88.7(7)
72.8(6)
Sb(2)
O(1)
–303(1) 10630(1) 2798(1)
–559(1) 11704(1) 2361(1)
43(2) 11886(2) 1615(1)
904(2) 11021(2) 1307(1)
4619(1)
1328(1)
5559(1)
1523(1)
5398(1)
4297(1)
1569(1)
1485(2)
5970(2)
5784(3)
4714(3)
5631(1)
6461(1)
6715(1)
6142(1)
5312(1)
5059(1)
5525(1)
6434(1)
6608(2)
5874(2)
4959(2)
4793(2)
6388(1)
6177(1)
6988(1)
7999(2)
8226(1)
7426(1)
3520(1)
3299(1)
2214(1)
1352(1)
1557(1)
2638(1)
6398(1)
6459(2)
7400(2)
8276(2)
8253(2)
7310(1)
3949(1)
6270(1)
4183(1)
6107(1)
5081(1)
5835(2)
5178(1)
4286(1)
–609(2)
–1178(3)
–391(3)
479(1)
1905(1)
3583(1)
1605(1)
4344(1)
1082(1)
832(1)
61.2(3) C(63)
58.3(3) C(64)
57.8(4) C(65)
59.5(4) C(66)
53.4(4) C(71)
80.5(7) C(72)
54.1(5) C(73)
74.2(6) C(74)
O(2)
N(1)
N(2)
1161(1)
2633(1)
2881(1)
3979(1)
4825(1)
4578(1)
3492(1)
–247(1)
13(1)
9964(1) 1748(1)
7642(1) 3067(1)
8438(1) 3180(1)
8222(2) 3164(1)
7222(2) 3007(1)
6446(2) 2878(1)
6640(1) 2914(1)
8392(1) 4131(1)
8548(2) 4756(1)
8881(2) 5409(1)
9053(2) 5432(1)
8900(2) 4816(1)
8567(1) 4169(1)
7655(1) 2175(1)
8437(1) 1832(1)
8229(2) 1238(1)
C(1)
C(2)
C(3)
4794(1)
4545(1)
9642(2)
10590(3)
10833(3)
3040(1)
2704(1)
3106(1)
3860(1)
4203(1)
3803(1)
3370(1)
3715(1)
4356(1)
4658(1)
4325(1)
3671(1)
1405(1)
840(1)
C(4)
C(5)
170(1)
271(2)
233(2)
C(75)
C(76)
C(81)
C(6)
C(7)
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)
C(43)
C(44)
C(45)
C(46)
C(51)
C(52)
C(53)
C(54)
C(55)
C(56)
44.3(4) C(82)
57.1(5) C(83)
68.8(6) C(84)
65.6(5) C(85)
62.4(5) C(86)
54.8(4) C(91)
49.8(4) C(92)
63.6(5) C(93)
85.6(6) C(94)
92.0(6) C(95)
93.4(7) C(96)
71.4(6) C(101)
45.4(4) C(102)
59.3(5) C(103)
70.3(5) C(104)
73.3(6) C(105)
79.7(6) C(106)
66.8(5)
–399(1)
–1475(1)
–1702(1)
–852(1)
229(1)
–820(2)
–1884(2)
–2138(1)
–1327(1)
535(1)
2617(1)
1896(1)
2127(2)
3038(2)
3750(2)
3553(1)
1846(1)
1513(1)
1215(2)
1221(2)
1515(2)
1838(2)
2507(1)
1662(1)
1835(1)
2832(2)
3662(2)
3509(1)
5327(1)
6022(1)
6224(2)
5768(2)
5065(2)
4854(2)
–369(1)
–642(1)
–5(2)
7256(2)
968(1)
909(2)
6469(2) 1299(1)
6668(1) 1904(1)
5025(1) 5613(1)
4374(1) 6252(1)
4275(2) 7016(1)
4791(2) 7155(1)
5434(2) 6528(1)
5557(2) 5772(1)
II
1173(1)
1712(1)
1289(1)
1393(2)
1943(2)
2368(2)
2245(2)
171(1)
81(1)
648(1)
1303(1)
2478(1)
2405(1)
2432(1)
2560(1)
2642(1)
2588(1)
710(1)
45.0(4) Sb
333.3(2) 5379.2(1) 2189.7(1)
47.62(9)
59.5(6)
134(1)
140(1)
59.0(7)
90(1)
52.6(4) O(1)
63.3(5) O(2)
69.1(6) O(3)
71.0(6) N(1)
60.0(5) N(2)
54.7(4) C(1)
74.6(6) C(11)
85.2(7) C(12)
86.6(7) C(13)
87.8(7) C(14)
75.2(6) C(15)
1028(2)
5850(4)
7471(3)
2245(2)
6441(4)
2821(3)
4135(3)
4844(4)
6087(4)
6630(4)
5909(4)
6125(1) 1354(1)
4013(2) 1695(2)
4128(2) 1094(2)
5864(2) 1273(1)
4367(3) 1264(2)
6266(2)
6041(2)
6501(2)
6272(3)
5587(3)
5129(3)
819(2)
699(2)
257(2)
137(2)
460(2)
904(2)
61.6(9)
59.6(9)
75(1)
–30(1)
–395(1)
–27(1)
84(1)
705(1)
80(1)
1061(1)
71(1)
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 28 No. 8 2002

SYNTHESIS AND STRUCTURES OF TETRA- AND TRIARYLANTIMONY OXIMATES
Table 2. (Contd.)
547
Atom
x
y
z
Ueq, Å2
Atom
x
y
z
Ueq, Å2
II
III
C(16)
C(21)
C(22)
C(23)
C(24)
C(25)
C(26)
C(27)
C(31)
C(32)
C(33)
C(34)
C(35)
C(36)
C(37)
C(41)
C(42)
C(43)
C(44)
C(45)
C(46)
C(47)
C(51)
C(52)
C(53)
C(54)
C(55)
C(56)
C(57)
4688(3)
581(3)
5347(2)
4325(2)
4356(2)
3657(2)
2908(2)
2888(2)
3588(2)
2149(2)
4689(2)
5050(2)
4727(2)
4023(2)
3652(2)
3982(2)
3696(3)
6210(2)
6002(2)
6539(3)
7291(2)
7500(2)
6972(2)
7877(3)
5774(2)
6593(3)
6819(3)
6248(4)
5436(3)
5197(3)
6493(4)
III
1033(2)
1535(2)
816(2)
63.4(9)
47.1(8)
53.7(8)
57.5(9)
56.0(8)
65.0(9)
62.9(9)
85(1)
C(16)
C(21)
C(22)
C(23)
C(24)
C(25)
C(26)
C(27)
C(31)
C(32)
C(33)
C(34)
C(35)
C(36)
C(37)
C(41)
C(42)
C(43)
C(44)
C(45)
C(46)
C(47)
C(51)
C(52)
C(53)
C(54)
C(55)
C(56)
Sb(2)
O(3)
1579(4)
6215(3)
5997(3)
6689(3)
7606(3)
7827(3)
7140(3)
8315(4)
5872(3)
6068(4)
6619(4)
6996(4)
6815(3)
6252(3)
7603(4)
3460(3)
3134(4)
2023(5)
1214(5)
1559(5)
2663(4)
–21(5)
8700(3) –1467(3)
95(1)
56.2(9)
64(1)
8321(2)
9230(2)
9848(3)
9601(3)
8701(3)
8063(3)
10282(3)
6894(3)
5993(3)
5735(3)
1598(2)
1776(2)
2344(2)
2752(2)
2562(2)
1996(2)
3391(2)
–137(2)
–347(2)
–903(2)
289(3)
423(3)
410(2)
73(1)
864(3)
694(2)
67(1)
1176(3)
1016(3)
1006(4)
–488(3)
–434(3)
–1123(4)
–1872(3)
–1891(3)
–1228(3)
–2641(4)
–1254(3)
–2398(3)
–3429(3)
–3360(3)
–2210(3)
–1167(3)
–4489(4)
1969(3)
2234(4)
3327(5)
4174(4)
3902(4)
2811(4)
5409(4)
1406(2)
1820(2)
241(2)
69(1)
65(1)
104(2)
64(1)
3043(2)
3704(2)
4235(2)
4123(2)
3471(2)
2943(2)
4710(2)
2053(2)
2318(2)
2238(2)
1898(2)
1635(2)
1704(2)
1821(2)
2820(2)
2953(2)
3355(2)
3608(2)
3474(3)
3086(2)
4037(2)
49.9(8)
63.0(9)
73(1)
101(2)
109(2)
85(1)
68(1)
6361(4) –1252(2)
7260(4) –1035(2)
72(1)
81(1)
62.4(9)
108(2)
47.9(8)
57.1(9)
65(1)
7535(3)
–493(2)
73(1)
6067(4) –1857(2)
136(2)
67(1)
6943(3)
7314(3)
7112(4)
6502(4)
6121(4)
6336(3)
6295(5)
5503(3)
4842(3)
4786(4)
5377(4)
6041(4)
6091(3)
870(2)
1487(3)
1587(3)
1066(4)
464(3)
100(1)
120(2)
111(2)
131(2)
108(2)
173(3)
69(1)
62.7(9)
60.7(9)
54.7(8)
96(1)
365(2)
1182(4)
2694(2)
3050(3)
3679(3)
3954(3)
3609(3)
2993(2)
53.5(8)
83(1)
5466(3)
5805(4)
5477(5)
4791(5)
4443(4)
4768(4)
101(2)
117(2)
108(2)
110(2)
97(1)
97(1)
83(1)
111(2)
97(1)
130(2)
7608.8(2) 9700.9(2) 6951.8(1)
52.61(8)
61.5(6)
57.4(6)
59.8(7)
56.0(7)
57.0(9)
54.8(9)
91(1)
6392(2)
8840(2)
5461(2)
8956(2)
4694(3)
9422(3)
9773(4)
4769(3)
9575(4)
9100(2)
10258(1)
8648(2)
7417(1)
6468(1)
6884(2)
6661(1)
7084.0(2)
6246(2)
5600(2)
7834(2)
6423(2)
6364(2)
6537(3)
6759(4)
6815(3)
6652(2)
6532(2)
Sb(1)
O(1)
O(2)
N(1)
N(2)
C(1)
5139.5(2) 7346.0(2)
747.2(1)
362(1)
61.99(9) O(4)
4606(2)
5743(2)
3734(3)
5403(3)
3180(3)
5809(3)
3425(3)
6585(4)
2228(3)
1956(4)
1043(4)
398(4)
8468(2)
6233(2)
8053(2)
6203(2)
8621(3)
5578(3)
9658(2)
4947(3)
8186(3)
7241(3)
6827(4)
7347(4)
8271(4)
67.9(7)
73.4(7)
63.6(8)
67.3(8)
60.0(9)
71(1)
N(3)
N(4)
C(3)
C(4)
C(5)
C(6)
C(61)
1099(1)
–227(2)
1738(2)
–500(2)
2025(2)
–229(2)
1713(2)
–1102(2)
–1310(2)
–1853(3)
–2199(3)
–2020(3)
11240(2)
8152(2)
11637(2)
11134(3)
8075(3)
C(2)
89(1)
C(7)
88(1)
12662(3)
13181(3)
14161(5)
14582(5)
14095(4)
13123(3)
7667(2)
65(1)
C(8)
119(2)
62.2(9)
94(1)
C(62) 10557(4)
C(63) 10681(7)
101(2)
138(3)
157(4)
139(2)
97(1)
C(11)
C(12)
C(13)
C(14)
C(15)
C(64)
C(65)
C(66)
C(71)
9826(9)
8849(6)
8725(4)
3695(3)
110(2)
99(1)
665(4)
109(2)
58.1(9)
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 28 No. 8 2002

548
SHARUTIN et al.
Table 2. (Contd.)
Atom
x
y
z
Ueq, Å2
Atom
x
y
z
Ueq, Å2
III
IV
C(72)
C(73)
C(74)
C(75)
C(76)
C(81)
C(82)
C(83)
C(84)
C(85)
C(86)
C(87)
C(91)
C(92)
C(93)
C(94)
C(95)
C(96)
C(97)
C(101)
C(102)
C(103)
C(104)
C(105)
C(106)
C(107)
2681(3)
1744(4)
1813(4)
2811(4)
3746(4)
8543(3)
9695(3)
10305(3)
9780(4)
8620(5)
7994(4)
10441(5)
7927(3)
7485(3)
7643(3)
8233(3)
8698(3)
8545(3)
8367(4)
6402(3)
6418(3)
5601(4)
4761(4)
4774(3)
5579(3)
3827(4)
7314(3)
6892(3)
6691(2)
6165(3)
5480(3)
5319(2)
5832(2)
7970(2)
8092(2)
8757(2)
9314(2)
9186(2)
8527(2)
78(1)
92(1)
92(1)
100(1)
88(1)
N(2)
7947(3)
6182(3)
6578(4)
6156(5)
4699(5)
4428(4)
4790(3)
–999(2)
3177(2)
3925(2)
4807(3)
4808(3)
4092(3)
3190(2)
9168(2)
8895(2)
9417(2)
9073(2)
8761(2)
8200(2)
8528(2)
9091(2)
9501(2)
9921(2)
9417(3)
9073(3)
8631(2)
8203(2)
8604(2)
8319(3)
7645(3)
7245(2)
7528(2)
9713(2)
53.4(7)
50.3(8)
77(1)
83(1)
86(1)
82(1)
70(1)
49(1)
69(1)
85(1)
89(1)
88(1)
62(1)
43(1)
65(1)
81(1)
74(1)
83(1)
65(1)
44(1)
55(1)
69(1)
68(1)
74(1)
62(1)
40(1)
50(1)
59(1)
64(1)
64(1)
54(1)
C(11)
C(12)
C(13)
C(14)
6810(3)
7142(3)
7562(3)
10311(2)
10608(3)
11016(3)
11182(4)
10934(5)
10491(4)
59.2(9) C(15)
69(1)
85(1)
C(16)
C(21)
C(22)
C(23)
C(24)
C(25)
8300(3) –1794(2)
7591(4) –2480(2)
8517(5) –3127(3)
9477(4) –3505(3)
10250(4) –2786(3)
9333(3) –2131(2)
119(2)
153(3)
121(2)
196(4)
11682(5) 10044(2)
8379(2)
7577(3)
6711(3)
6603(2)
7405(3)
8270(2)
5652(3)
10432(2)
10586(3)
11042(3)
11371(3)
11233(3)
10767(3)
11844(4)
IV
6442(2)
6622(2)
6268(2)
5725(2)
5559(2)
5912(2)
5318(2)
6469(2)
5809(2)
5499(2)
5843(3)
6501(3)
6818(2)
5490(3)
49.8(8) C(26)
68(1)
73(1)
65(1)
68(1)
C(31)
C(32)
C(33)
C(34)
9296(3)
10518(3)
11616(4)
11505(4)
10313(5)
9205(4)
7133(3)
8071(3)
7755(4)
6494(4)
5547(4)
5861(3)
6195(3)
4985(3)
4091(3)
4410(4)
5605(4)
6485(3)
1291(2)
1214(3)
1567(3)
1987(3)
2056(3)
1723(2)
841(2)
62.0(9) C(35)
97(1) C(36)
56.0(9) C(41)
71(1)
84(1)
85(1)
87(1)
71(1)
131(2)
C(42)
C(43)
C(44)
C(45)
C(46)
C(51)
C(52)
673(2) 10308(2)
728(3) 11043(2)
934(2) 11182(2)
1080(3) 10601(2)
1046(2)
162(2)
9869(2)
7776(2)
7579(2)
7040(2)
6695(2)
6883(2)
7431(2)
554(2)
Sb
7571.2(2)
6546(2)
8656(2)
7040(3)
756.2(1) 8591.0(1)
38.9(1) C(53)
46.6(5) C(54)
47.3(5) C(55)
51.8(7) C(56)
170(2)
O(1)
O(2)
N(1)
1897(1)
–384(1)
2581(2)
8322(1)
8766(1)
8810(1)
–590(2)
–980(2)
–614(2)
Ar5Sb + Ar3Sb(ON=CRR')2
2Ar4SbON=CRR'.
359.12(6)° (Ib), and 358.1(1)° (II); the axial angles
OSbC are equal to 175.72(4)°, 175.31(5)°, and
175.7(1)° for molecules Ia, Ib, and II, respectively.
The OaxSbCeq and CaxSbCeq bond angles in structures I
and II lie within the range of 82.4(1)°–89.40(5)° and
92.24(5)°–96.1(1)°, respectively. The Sb–Ceq bond
lengths lie within the range of 2.114(1)–2.131(2) Å for
compound I and 2.121(3)–2.135(3) Å for compound II.
The axial Sb–Cax bonds (2.193(1) (Ia), 2.207(1) (Ib),
and 2.187(3) (II) Å) are noticeably longer than the
equatorial bonds. The Sb–Oax bonds (2.138(1),
2.137(2), and 2.154(2) Å in Ia, Ib, and II, respectively)
are noticeably shorter than the Sb–Cax bonds. The Sb–
Triarylantimony dioximates were synthesized from
triarylstibine, oxime, and hydrogen peroxide (molar
ratio of 1 : 2 : 1) via the reaction of oxidative addition:
Ar3Sb + 2HON=CRR' + H2O2
Ar3Sb(ON=CRR')2 + 2H2O.
According to X-ray diffraction data, crystals I con-
sist of two individual molecules (a and b) with close
parameters. The antimony atoms in compounds I and II
have virtually undistorted trigonal-bipyramidal coordi-
nation with the axial O atoms (Fig. 1, 2). The sums of
the CeqSbCeq bond angles are equal to 359.05(6)° (Ia), Oax distance in compound II agrees with the analogous
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 28 No. 8 2002

SYNTHESIS AND STRUCTURES OF TETRA- AND TRIARYLANTIMONY OXIMATES
Table 3. Bond lengths and angles in structures I–IV
549
Bond
d, Å
Angle
ω, deg
Bond
d, Å
Angle
ω, deg
I
O(2)–N(2)
1.401(3) O(2)Sb(1)C(21)
1.272(4) O(1)Sb(1)C(21)
1.277(4) C(41)Sb(1)C(21)
1.481(5) C(31)Sb(1)C(21)
1.499(5) N(1)O(1)Sb(1)
1.473(5) N(2)O(2)Sb(1)
1.499(5) C(1)N(1)O(1)
92.2(1)
87.8(1)
Sb(1)–C(31)
Sb(1)–C(41)
Sb(1)–C(21)
Sb(1)–O(1)
Sb(1)–C(11)
O(1)–N(1)
2.114(1) C(31)Sb(1)C(41)
2.122(2) C(31)Sb(1)C(21)
2.123(2) C(41)Sb(1)C(21)
2.138(1) C(31)Sb(1)O(1)
2.193(1) C(41)Sb(1)O(1)
1.390(2) C(21)Sb(1)O(1)
1.278(2) C(31)Sb(1)C(11)
2.114(2) C(41)Sb(1)C(11)
2.117(1) C(21)Sb(1)C(11)
2.131(2) O(1)Sb(1)C(11)
2.137(1) N(1)O(1)Sb(1)
2.207(1) C(1)N(1)O(1)
1.402(2) N(1)C(1)C(51)
1.279(2) N(1)C(1)C(2)
C(71)Sb(2)C(81)
118.89(6) N(1)–C(1)
121.19(6) N(2)–C(2)
118.97(5) C(1)–C(11)
89.40(5) C(1)–C(7)
82.85(5) C(2)–C(51)
87.92(5) C(2)–C(8)
93.87(5) C(11)–C(12) 1.363(5) C(2)N(2)O(2)
93.14(5) C(11)–C(16) 1.364(5) N(1)C(1)C(11)
92.74(6) C(12)–C(13) 1.381(5) N(1)C(1)C(7)
175.72(4) C(13)–C(14) 1.348(6) C(32)C(31)Sb(1)
106.97(7) C(14)–C(15) 1.329(6) C(36)C(31)Sb(1)
116.7(1)
116.1(1)
104.0(2)
108.7(2)
115.0(3)
113.4(3)
115.3(3)
123.6(3)
122.6(3)
119.5(3)
123.5(3)
119.0(3)
177.99(8)
87.4(1)
N(1)–C(1)
Sb(2)–C(71)
Sb(2)–C(81)
Sb(2)–C(91)
Sb(2)–O(2)
Sb(2)–C(61)
O(2)–N(2)
113.6(1)
115.4(1)
123.7(2)
C(15)–C(16) 1.397(6) C(46)C(41)Sb(1)
C(21)–C(26) 1.380(4) C(42)C(41)Sb(1)
Sb(2)–O(3)
N(2)–C(3)
2.066(2) O(3)Sb(2)O(4)
2.075(2) O(3)Sb(2)C(81)
119.17(6) Sb(2)–O(4)
C(71)Sb(2)C(91)
C(81)Sb(2)C(91)
C(71)Sb(2)O(2)
120.55(5) Sb(2)–C(81) 2.097(3) O(4)Sb(2)C(81)
119.40(6) Sb(2)–C(101) 2.108(3) O(3)Sb(2)C(101)
88.44(5) Sb(2)–C(91) 2.112(3) O(4)Sb(2)C(101)
93.6(1)
91.6(1)
89.5(1)
C(81)Sb(2)O(2)
C(91)Sb(2)O(2)
C(71)Sb(2)C(61)
C(81)Sb(2)C(61)
C(91)Sb(2)C(61)
O(2)Sb(2)C(61)
N(2)O(2)Sb(2)
C(3)N(2)O(2)
89.10(5) O(3)–N(3)
83.12(5) O(4)–N(4)
93.34(5) N(3)–C(3)
93.81(6) N(4)–C(4)
92.24(6) C(3)–C(71)
175.31(5) C(3)–C(6)
104.62(8) C(4)–C(61)
1.396(3) C(81)Sb(2)C(101)
1.410(3) O(3)Sb(2)C(91)
1.278(4) O(4)Sb(2)C(91)
1.271(4) C(81)Sb(2)C(91)
1.479(5) C(101)Sb(2)C(91)
1.502(5) N(3)O(3)Sb(2)
1.471(5) N(4)O(4)Sb(2)
1.490(5) C(3)N(3)O(3)
119.0(1)
91.6(1)
86.4(1)
118.7(1)
122.3(1)
107.7(2)
109.0(2)
114.7(3)
113.3(3)
116.0(3)
123.0(3)
120.9(3)
115.9(3)
124.5(3)
121.3(3)
120.7(3)
122.2(2)
120.5(3)
114.4(2)
114.8(2)
124.8(2)
C(4)–C(5)
N(2)C(3)C(101)
N(2)C(3)C(4)
II
C(61)–C(62) 1.367(5) C(4)N(4)O(4)
C(61)–C(66) 1.369(5) N(3)C(3)C(71)
C(62)–C(63) 1.407(7) N(3)C(3)C(6)
C(63)–C(64) 1.339(9) C(71)C(3)C(6)
C(64)–C(65) 1.338(8) N(4)C(4)C(61)
C(65)–C(66) 1.394(7) N(4)C(4)C(5)
C(71)–C(76) 1.377(5) C(82)C(81)Sb(2)
C(71)–C(72) 1.378(5) C(86)C(81)Sb(2)
C(72)–C(73) 1.383(5) C(96)C(91)Sb(2)
C(73)–C(74) 1.355(6) C(92)C(91)Sb(2)
Sb–C(21)
Sb–C(51)
Sb–C(41)
Sb–O(1)
Sb–C(31)
O(1)–N(1)
O(2)–N(2)
O(3)–N(2)
N(1)–C(1)
N(2)–C(15)
2.121(3) C(21)SbC(51)
2.127(3) C(21)SbC(41)
2.135(3) C(51)SbC(41)
2.154(2) C(21)SbO(1)
2.187(3) C(51)SbO(1)
1.365(3) C(41)SbO(1)
1.203(4) C(21)SbC(31)
1.213(4) C(51)SbC(31)
1.263(4) C(41)SbC(31)
1.486(5) O(1)SbC(31)
C(42)C(41)Sb
116.1(1)
123.2(1)
118.8(1)
86.8(1)
87.2(1)
82.4(1)
96.1(1)
94.4(1)
93.3(1)
175.7(1)
120.1(2)
C(74)–C(75) 1.354(6) C(106)C(101)Sb(2) 119.5(3)
C(75)–C(76) 1.369(5) C(102)C(101)Sb(2) 121.7(3)
IV
Sb–O(1)
2.058(2) O(1)–Sb–O(2)
2.064(2) O(1)–Sb–C(41)
2.097(3) O(2)–Sb–C(41)
2.113(3) O(1)–Sb–C(31)
2.118(3) O(2)–Sb–C(31)
2.864(3) C(41)–Sb–C(31)
2.874(3) O(1)–Sb–C(51)
1.416(3) O(2)–Sb–C(51)
1.419(3) C(41)–Sb–C(51)
1.279(4) C(31)–Sb–C(51)
1.273(4) C(11)–N(1)–O(1)
174.89(8)
91.1(1)
93.9(1)
90.9(1)
85.7(1)
123.4(1)
85.1(1)
93.0(1)
119.5(1)
117.0(1)
112.9(2)
114.2(3)
125.7(3)
117.9(3)
127.5(3)
117.1(3)
C(46)C(41)Sb
C(56)C(51)Sb
C(52)C(51)Sb
N(1)O(1)Sb
C(1)N(1)O(1)
O(2)N(2)O(3)
O(2)N(2)C(15)
O(3)N(2)C(15)
N(1)C(1)C(11)
121.6(2)
119.6(3)
122.6(3)
106.4(2)
114.7(3)
123.0(5)
120.2(4)
116.8(4)
118.9(3)
Sb–O(2)
Sb–C(41)
Sb–C(31)
Sb–C(51)
Sb–N(1)
Sb–N(2)
O(1)–N(1)
O(2)–N(2)
N(1)–C(11)
N(2)–C(21)
III
Sb(1)–O(2)
Sb(1)–O(1)
Sb(1)–C(41)
Sb(1)–C(31)
Sb(1)–C(21)
O(1)–N(1)
2.067(2) O(2)Sb(1)O(1)
2.080(2) O(2)Sb(1)C(41)
2.099(4) O(1)Sb(1)C(41)
2.106(4) O(2)Sb(1)C(31)
2.107(3) O(1)Sb(1)C(31)
1.406(3) C(41)Sb(1)C(31)
176.81(9) C(51)–C(52) 1.382(4) C(21)–N(2)–O(2)
92.8(1)
90.1(1)
85.8(1)
91.4(1)
127.3(1)
N(1)–C(11)–C(16)
N(1)–C(11)–C(12)
N(2)–C(21)–C(26)
N(2)–C(21)–C(22)
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 28 No. 8 2002

550
SHARUTIN et al.
C(104)
C(105)
C(106)
C(103)
C(102)
C(74)
C(75)
C(73)
C(101)
C(33)
C(32)
C(82)
C(76)
C(44)
C(42)
C(34)
C(35)
C(72)
C(3)
C(4)
C(2)
C(1)
C(52)
C(45)
N(2)
C(43)
C(31)
C(71)
C(81)
C(83)
C(84)
C(53)
C(36)
O(1)
O(2)
C(12)
C(51)
C(56)
Sb(2)
C(86)
C(41)
C(54)
C(55)
C(61)
N(1)
C(13)
C(14)
C(62)
C(46)
Sb(1)
C(96)
C(95)
C(11)
C(16)
C(63)
C(66)
C(65)
C(91)
C(21)
C(85)
C(64)
C(15)
C(92)
C(94)
C(26)
C(25)
C(22)
C(23)
C(93)
C(24)
Fig. 1. Molecular structure of tetraphenylantimony acetophenoneoximate (I).
C(27)
C(13)
C(12)
C(23)
C(24)
C(14)
C(15)
C(1)
C(22)
C(25)
O(3)
C(11)
C(16)
N(2)
N(1)
C(21)
O(1)
C(26)
O(2)
C(46)
C(41)
C(45)
C(44)
C(47)
C(42)
Sb
C(31)
C(32)
C(43)
C(36)
C(56)
C(51)
C(52)
C(55)
C(53)
C(35)
C(34)
C(54)
C(57)
C(33)
C(37)
Fig. 2. Molecular structure of tetra-n-tolylantimony 3-nitrobenzaloximate (II).
distances in other structurally characterized tetraphe- Sb–Oax bonds are found to be noticeably longer (2.223–
2.530 Å) [10–14].
nylantimony oximates (2.150(3)–2.146(4 [8, 9]) Å).
Similar Sb–O distances (2.121(4)–2.143(4) Å) are
observed in aroxytetraarylantimony compounds con-
taining electron-donating substutuents in the aroxy
In structures I and II, the Sb atom is involved in
intramolecular contact with the N atom of the oxime
group. The Sb···N distance (2.871(1) (Ia), 2.836(1)
group [6, 7], while in tetraarylantimony acylates, the (Ib), and 2.857(3) (II) Å) is noticeably shorter than the
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SYNTHESIS AND STRUCTURES OF TETRA- AND TRIARYLANTIMONY OXIMATES
551
C(107)
C(104)
C(105)
C(103)
C(65)
C(74)
C(66)
C(64)
C(63)
C(106)
C(102)
C(75)
C(76)
C(73)
C(72)
C(101)
C(4)
C(62)
C(3)
C(61)
C(71)
C(6)
N(3)
N(4)
Sb(2)
O(3)
C(5)
O(4)
C(86)
C(81)
C(91)
C(92)
C(93)
C(82)
C(83)
C(96)
C(95)
C(94)
C(85)
C(97)
C(84)
C(87)
C(47)
C(44)
C(43)
C(42)
C(45)
C(46)
C(14)
C(55)
C(54)
C(13)
C(12)
C(56)
C(51)
C(2)
C(15)
C(16)
C(53)
C(52)
C(41)
C(11)
C(7)
C(1)
N(2)
N(1)
Sb(1)
O(2)
C(8)
O(1)
C(31)
C(36)
C(21)
C(22)
C(32)
C(26)
C(25)
C(23)
C(33)
C(34)
C(35)
C(24)
C(27)
C(37)
Fig. 3. Molecular structure of tri-n-tolylantimony bis(acetophenoneoximate) (III).
sum of the van der Waals radii of Sb and N atoms (3.8 Å nylantimony acylates, the intramolecular contact
[21]). In tetraarylantimony acylates, the intramolecular Sb···O=C more greatly influences the equatorial angles
contact Sb···O=C is less pronounced (the Sb···O dis- (129.3(1)°–143.3(2)°) [10–12].
tances vary within range the 3.0–3.3 Å [10–12]). Closer
contact of the central atom with the nitrogen atom is
likely due to the Sb–O bond in tetraarylantimony oxi-
mates I and II being shorter than that in tetraarylanti-
mony acylates. Bidentate coordination of the oximate
ligand was also observed in µ-oxo-bis[(furfuroloxi-
mato)triphenylantimony] [17].
The SbON angles in molecules Ia, Ib, and II are
equal to 106.97(7)°, 104.62(7)°, and 106.4(2)°, respec-
tively. The lengths of the O–N bonds (1.390(2),
1.402(2), and 1.365(3) Å) and of the N–C bonds
(1.278(2), 1.279(2), and 1.263(4) Å) are similar to the
lengths of the analogous bonds in other tetraphenylan-
timony oximates [8, 9]. In compound II, the lengths of
the N–O bonds in the nitro group (1.203(4) and
1.213(4) Å) and the O(2)N(2)O(3) angle (123.0(5)°)
show normal values [22].
The intramolecular contact Sb···N in compound I
does not influence the CeqSbCeq angles, which are close
to the ideal value of 120° (118.97(5)°–121.19(6)°). In
compound II, one of the equatorial angles CSbC (from
The X-ray diffraction analysis of compounds III
the side of the Sb···N contact) is slightly greater than the and IV indicates a trigonal-bipyramidal coordination of
other two angles (123.2(1)°, 116.1(1)°, and 118.8(1)°). Sb atoms to O atoms of the axial oxime ligands (Fig. 3,
The intramolecular contacts Sb···N in two independent 4). There are two individual molecules (a and b) in
molecules of tetraphenylantimony furfuroloximate and crystal III. The sums of the CSbC angles in the equato-
in tetraphenylantimony benzophenoneoximate are rial planes of structures III and IV differ from 360° by
equal to 2.841(5), 2.940(6), and 2.964(5) Å, respec- less than 0.1°. However, the individual angles CeqSbCeq
tively; the equatorial angles CSbC in these compounds are different: 116.7(1)°, 116.1(1)°, and 127.3(1)° in
also insignificantly change [8, 9]. Note that in tetraphe- IIIa; 118.7(1)°, 119.0(1)°, and 122.3(1)° in IIIb;
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 28 No. 8 2002

552
SHARUTIN et al.
C(53)
C(15)
C(52)
C(54)
C(55)
C(14)
C(13)
C(16)
C(11)
C(45)
C(44)
O(1)
C(43)
C(46)
C(41)
C(56)
C(51)
C(12)
C(22)
Sb
C(42)
N(1)
C(21)
N(2)
C(23)
C(24)
O(2)
C(26)
C(36)
C(31)
C(32)
C(25)
C(35)
C(34)
C(33)
Fig. 4. Molecular structure of triphenylantimony bis(cyclohexanoneoximate) (IV).
117.0(1)°, 119.5(1)°, and 123.4(1)° in IV. The axial
angles OSbO are equal to 176.81(9)° (IIIa), 177.99(8)°
(IIIb), and 174.89(8)° (IV). The Sb–C bond lengths lie
within the range of 2.099(4)–2.107(3) Å (IIIa),
2.097(3)–2.112(3) Å (IIIb), and 2.097(3)–2.118(3)
(IV); the Sb–Oax bonds (2.066(2)–2.080(1) Å in III;
2.058(2) and 2.064(2) Å in IV) are shorter than the Sb–
Ceq bonds. It should be noted that in triarylantimony
dioximates, the Sb–O bond length is close to the sum of
the covalent radii of antimony and oxygen atoms (2.07
Å [21]); the corresponding bond in triarylantimony dia-
cylates [14–17] and triarylantimony disulfonates [17,
23, 24] is noticeably shorter; while it is longer in triph-
enylantimony dimethoxide [4].
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