Tetra-p-Tolylantimony 4-Methylbenzenesulfonate: Synthesis and Structure

DOI: 10.1023/A:1023667500059

Source and publish data:

Russian Journal of Coordination Chemistry p. 312 - 316 (2003)

Update date:2022-07-29

Topics:

Authors:

Sharutin

Pakusina

Egorova Egorova

Ivanenko

Gerasimenko

Sergienko

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Article abstract of DOI:10.1023/A:1023667500059

Tetra-p-tolylantimony 4-methylbenzenesulfonate (I) was synthesized via the reaction of tri-p-tolylbismuth bis(4-methylbenzenesulfonate) with penta-p-tolylantimony in toluene. According to the X-ray diffraction data, the antimony atoms of two individual molecules of I have a distorted trigonal bipyramidal coordination with the axial 4-methylbenzenesulfonate ligand and three equatorial tolyl ligands, one of which contains four carbon atoms disordered over two sites with the occupancy factors 0.7 and 0.3.

Full text of DOI:10.1023/A:1023667500059

Russian Journal of Coordination Chemistry, Vol. 29, No. 5, 2003, pp. 312–316. Translated from Koordinatsionnaya Khimiya, Vol. 29, No. 5, 2003, pp. 336–340.

Tetra-p-Tolylantimony 4-Methylbenzenesulfonate:

Synthesis and Structure

V. V. Sharutin, A. P. Pakusina, I. V. Egorova, T. K. Ivanenko,

A. V. Gerasimenko, and A. S. Sergienko

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 July 23, 2001

Abstract—Tetra-p-tolylantimony 4-methylbenzenesulfonate (I) was synthesized via the reaction of tri-p-tolyl-

bismuth bis(4-methylbenzenesulfonate) with penta-p-tolylantimony in toluene. According to the X-ray diffrac-

tion data, the antimony atoms of two individual molecules of I have a distorted trigonal bipyramidal coordina-

tion with the axial 4-methylbenzenesulfonate ligand and three equatorial tolyl ligands, one of which contains

four carbon atoms disordered over two sites with the occupancy factors 0.7 and 0.3.

Tetra-p-tolylantimony 4-methylbenzenesulfonate tetra-p-tolylantimony and tetra-p-tolylbismuth 4-meth-

ylbenzenesulfonates:

(I) can be synthesized using different reactions: interac-

tion of penta-p-tolylantimony with 4-methylbenzene-

sulfonic acid [1], introduction of sulfur oxide SO₃into

penta-p-tolylantimony at the Sb–C bond [2], or dispro-

portionation between penta-p-tolylantimony and tri-p-

tolylantimony bis(4-methylbenzenesulfonate) [3]. To

continue our studies of reactions of the third type, we

investigated the interaction of penta-p-tolylantimony

with tri-p-tolylbismuth bis(4-methylbenzenesulfonate).

These compounds were found to react in a solution of

p-Tol₅Sb + p-Tol₃BiX₂

p-Tol₄SbX + p-Tol₄BiX,

X = OSO₂C₆H₄Me-4.

For the reaction to be complete, the reaction mixture

should be heated at 90–100°ë for 1 h.

We believe that the synthesis of tetra-p-tolylanti-

mony and tetra-p-tolylbismuth 4-methylbenzene-

sulfonates proceeds through the formation of interme-

aromatic solvent even at a room temperature to yield diate labile ionic complex [p-Tol₄Sb]⁺[p-Tol₄BiX₂]^–.

Table 1. Crystallographic data and results of refinement of structure I

Parameter

Value

Parameter

Value

2688

F(000)

Empirical formula

C₃₅H₃₅O₃SSb

657.44

Crystal size, mm

θ, deg

Prism (0.15 × 0.20 × 0.25)

T, K

295(2)

1.62–26.53

Crystal system

Monoclinic

Range of reflection indices

–10 ≤ h ≤ 12,

–23 ≤ k ≤ 24, –41 ≤ l ≤ 41

Space group

P2₁/c

Total number of reflections

Independent reflections

Reflections with I > 2σ(I)

Number of refined parameters

GOOF

R-factors for F²> 2σ(F²)

R-factors for all reflections

Extinction coefficient

37704

13114 (R_int= 0.0549)

6827

Unit cell parameters:

a, Å

9.841(1)

19.227(2)

33.370(3)

90.416(2)

6314(1)

b, Å

802

c, Å

1.079

β, deg

V, Å³

R₁= 0.0705, wR₂= 0.1563

R₁= 0.1260, wR₂= 0.1697

0.00017(4)

ρ(calcd), g/cm³

µ_Mo, mm^–1

1.383

Residual electron density

–1.281/0.454

(in the neighborhood

of Sb atoms)

(min/max), e/Å³

0.972

TETRA-p-TOLYLANTIMONY 4-METHYLBENZENESULFONATE

313

C(3a)

(a‡)

C(35)

C(7)

C(4)

C(37)

C(34)

C(36)

C(31)

C(5b)

C(2a)

C(6b)

C(1)

C(3b)

C(5a)

C(33)

C(26)

C(6a)

C(2b)

C(32)

C(12)

Sb(1)

C(25)

C(13)

C(11)

C(14)

C(45)

C(46)

O(1)

C(21)

O(3)

O(2)

C(41)

C(47)

C(22)

C(23)

C(44)

C(24)

C(17)

S(1)

C(43)

C(42)

C(15)

C(16)

C(27)

C(87)

C(84)

(b)

C(65)

C(66)

C(83)

C(82)

C(67)

C(85)

C(64)

C(86)

C(81)

C(61)

C(63)

C(62)

C(56b)

C(56a)

C(53b)

C(52b)

C(71)

C(76)

Sb(2)

C(55a)

C(54)

C(75)

C(51)

C(74)

C(72)

C(56b)

C(73)

O(4)

C(52a)

C(57)

C(55b)

C(53a)

C(77)

S(2)

O(6)

C(92)

O(5)

C(93)

C(91)

C(96)

C(97)

C(95)

C(94)

Fig. 1. The structure of molecules (a) Ia and (b) Ib.

RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 29 No. 5 2003

314

SHARUTIN et al.

Table 2. Coordinates of atoms (×10⁴) and their isotropic equivalent thermal parameters for structure I

Atom

Sb(1)

U_eq, Å²

Atom

C(43)

U_eq, Å²

3374.4(3)

687.0(2) 1229.6(1)

59.6(1)

57.2(1)

65.3(4)

63.3(4)

92(1)

95(2)

105(2)

84(1)

94(2)

58(2)

77(3)

83(7)

90(3)

83(7)

81(2)

88(3)

91(7)

65(2)

70(6)

125(3)

58(2)

75(2)

84(2)

70(2)

75(2)

76(2)

114(3)

59(2)

68(2)

72(2)

64(2)

69(2)

63(2)

90(2)

52(1)

63(2)

66(2)

57(2)

60(2)

54(2)

80(2)

60(2)

107(3)

4031(9)

4606(8)

5560(8)

6053(8)

–1771(5)

–1583(4)

–1099(4)

–841(4)

2439(2)

2791(2)

2769(2)

2408(2)

3180(2)

1838(2)

2034(3)

1953(5)

2434(3)

2355(6)

2666(2)

2472(3)

2546(5)

2067(2)

2139(5)

3119(2)

1076(2)

996(2)

137(3)

93(2)

108(3)

116(3)

156(4)

57(2)

100(3)

45(4)

112(4)

62(5)

78(2)

89(3)

88(7)

80(3)

49(5)

115(3)

54(1)

65(2)

70(2)

63(2)

69(2)

65(2)

89(2)

53(1)

72(2)

79(2)

69(2)

76(2)

73(2)

114(3)

49(1)

66(2)

61(2)

55(2)

68(2)

64(2)

78(2)

58(2)

135(3)

181(4)

90(2)

112(3)

153(3)

144(4)

Sb(2)

S(1)

1669.6(3) 5679.3(2) 1230.2(1)

5861(1) –641.7(8) 1594.2(4)

–803(1) 4365.5(8) 1590.8(4)

C(44)

C(45)

C(46)

C(47)

C(51)

C(52a)*

S(2)

O(1)

4589(4)

6189(5)

6901(4)

500(4)

–311(2)

–1190(2)

–157(3)

4678(2)

3812(2)

4869(2)

957(3)

1472(1)

1326(1)

1662(1)

1481(1)

1323(1)

1655(1)

1839(2)

1954(3)

2038(6)

2360(3)

2442(6)

2661(2)

2544(3)

2466(6)

2140(2)

2056(5)

3102(2)

892(2)

4175(10) –1867(5)

O(2)

1638(5)

485(9)

5945(3)

6051(6)

6664(8)

6188(6)

6846(9)

6263(4)

6022(5)

5714(13)

5894(5)

5473(9)

6415(5)

4893(3)

4215(3)

3741(3)

3926(3)

4593(3)

5081(3)

3421(3)

5764(3)

6323(3)

6377(3)

5897(3)

5344(3)

5260(3)

5960(4)

6556(2)

6971(3)

7486(3)

7600(3)

7203(3)

6676(3)

8170(3)

3979(3)

3410(4)

3115(5)

3398(4)

3963(4)

4232(4)

3080(5)

O(3)

O(4)

C(52b)** 1440(14)

C(53a)* 456(10)

C(53b)** 1488(17)

O(5)

–1161(5)

–1830(4)

3430(5)

3569(8)

4491(18)

3588(9)

4510(20)

3419(6)

3329(8)

2270(20)

3297(8)

2199(15)

3447(7)

5160(5)

6005(6)

7156(6)

7527(5)

6652(6)

5494(6)

8837(6)

1958(5)

2303(5)

1313(6)

–28(5)

O(6)

C(1)

C(54)

1624(6)

2744(9)

C(2a)*

C(2b)**

C(3a)*

C(3b)**

C(4)

1669(5)

1029(12)

1859(5)

1181(11)

1328(4)

702(6)

C(55a)*

C(55b)** 1744(17)

C(56a)* 2787(8)

C(56b)** 1759(15)

C(57)

C(61)

C(62)

C(63)

C(64)

C(65)

C(66)

C(67)

C(71)

C(72)

C(73)

C(74)

C(75)

C(76)

C(77)

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)

1617(8)

3092(5)

2736(5)

3714(6)

5058(5)

5421(5)

4447(5)

6130(6)

–128(5)

–963(6)

–2127(6)

–2510(6)

–1639(6)

–477(6)

–3824(6)

2695(5)

3546(5)

4316(5)

4126(5)

3214(6)

2512(6)

4946(6)

–418(5)

348(9)

C(5a)*

C(5b)**

C(6a)*

C(6b)**

C(7)

1010(13)

479(4)

883(2)

873(11)

1495(5)

770(3)

869(2)

970(2)

C(11)

C(12)

C(13)

C(14)

C(15)

C(16)

C(17)

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)

1066(2)

746(2)

1324(3)

1389(4)

908(3)

942(2)

716(2)

891(2)

439(2)

937(2)

359(3)

391(2)

706(2)

270(3)

610(2)

432(2)

960(4)

199(2)

384(2)

–102(3)

–773(3)

–1244(3)

–1059(3)

–406(3)

81(3)

1078(2)

990(2)

613(2)

188(2)

876(2)

969(2)

863(2)

1184(2)

987(2)

–391(5)

596(5)

980(2)

1075(2)

742(2)

581(2)

–1102(6)

2339(5)

2567(6)

1825(6)

875(5)

–1588(4)

1560(3)

1701(3)

2227(3)

2610(3)

2477(3)

1961(3)

3176(3)

–1018(3)

–1493(4)

379(2)

967(2)

563(2)

566(2)

372(2)

380(2)

2057(2)

2080(2)

2435(2)

2794(2)

2771(2)

2407(2)

3187(2)

576(2)

663(5)

978(2)

688(11)

313(7)

1396(4)

67(6)

1177(2)

364(2)

–402(8)

–793(9)

715(10)

5431(5)

4414(8)

2058(2)

2076(2)

Notes: * The occupancy factor is equal to 0.7.

** The occupancy factor is equal to 0.3.

RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 29 No. 5 2003

TETRA-p-TOLYLANTIMONY 4-METHYLBENZENESULFONATE

Table 3. Bond lengths and angles in structure I

315

Bond

d, Å

Angle

ω, deg

Bond

d, Å

Angle

ω, deg

1.763(6)

C(71)Sb(2)O(4)

C(61)Sb(2)O(4)

81.1(2)

80.3(2)

Sb(1)–C(1)

Sb(1)–C(11)

Sb(1)–C(21)

Sb(1)–C(31)

Sb(1)–O(1)

Sb(2)–C(51)

Sb(2)–C(71)

Sb(2)–C(61)

Sb(2)–C(81)

Sb(2)–O(4)

S(1)–O(3)

2.098(5) C(1)Sb(1)C(11)

2.100(5) C(1)Sb(1)C(21)

2.120(5) C(11)Sb(1)C(21)

2.147(5) C(1)Sb(1)C(31)

2.398(4) C(11)Sb(1)C(31)

2.092(5) C(21)Sb(1)C(31)

2.099(5) C(1)Sb(1)O(1)

2.127(5) C(11)Sb(1)O(1)

2.153(5) C(21)Sb(1)O(1)

2.397(4) C(31)Sb(1)O(1)

1.401(4) C(51)Sb(2)C(71)

1.422(4) C(51)Sb(2)C(61)

1.460(4) C(71)Sb(2)C(61)

1.764(6) C(51)Sb(2)C(81)

1.418(4) C(71)Sb(2)C(81)

1.434(4) C(61)Sb(2)C(81)

1.465(4) C(51)Sb(2)O(4)

119.0(2)

114.9(2)

118.5(2)

102.1(2)

96.8(2)

98.8(2)

82.1(2)

79.9(2)

80.4(2)

175.6(2)

119.0(2)

115.0(2)

118.6(2)

102.2(2)

96.7(2)

98.5(2)

81.3(2)

S(2)–C(91)

C(1)–C(2b)

C(1)–C(6a)

C(1)–C(6b)

C(1)–C(2a)

C(2a)–C(3a)

C(2b)–C(3b)

C(3a)–C(4)

C(3b)–C(4)

C(4)–C(5a)

C(4)–C(5b)

C(4)–C(7)

1.24(2)

1.370(9)

1.43(2)

1.43(1)

1.40(1)

1.38(3)

1.44(1)

1.33(2)

1.27(1)

1.43(2)

1.507(9)

1.42(1)

1.39(3)

1.361(8)

1.385(8)

1.370(8)

C(81)Sb(2)O(4) 176.5(2)

O(3)S(1)O(2)

O(3)S(1)O(1)

O(2)S(1)O(1)

O(3)S(1)C(41)

O(2)S(1)C(41)

O(1)S(1)C(41)

O(6)S(2)O(5)

O(6)S(2)O(4)

O(5)S(2)O(4)

O(6)S(2)C(91)

O(5)S(2)C(91)

O(4)S(2)C(91)

S(1)O(1)Sb(1)

S(2)O(4)Sb(2)

115.2(3)

112.3(3)

110.1(3)

108.1(3)

107.8(3)

102.3(2)

115.4(3)

112.6(3)

111.1(3)

107.7(3)

106.8(3)

102.2(2)

150.1(3)

147.2(3)

S(1)–O(2)

S(1)–O(1)

C(5a)–C(6a)

C(5b)–C(6b)

C(11)–C(12)

C(11)–C(16)

C(12)–C(13)

S(1)–C(41)

S(2)–O(6)

S(2)–O(5)

S(2)–O(4)

Earlier, we have reported X-ray diffraction analysis angle between the substituents in the axial positions

of I [3]. In this work, the structure of this compound (C(31)Sb(1)O(1) 175.6(2)°, C(81)Sb(2)O(4) 176.5(2)°)

was reﬁned.

in structure I is somewhat less than that in structure II

(178.2(8)°) which is likely to be due to hindrances pro-

duced by a speciﬁc crystal packing. Really, in molecule

I, fragments C(2,3,5,6) and C(52,53,55,56) of one of

RESULTS AND DISCUSSION

The antimony atoms in two individual molecules I tolyl substituent are statistically disordered over two

(Figs. 1a and 1b) have a trigonal bipyramidal coordina-

tion typical of the most pentacoordinated antimony

complexes with the axial oxygen atoms of 4-methyl-

benzenesulfonate groups (as distinct from the structure

described in [3] containing identical molecules). The

Sb–O(1) distances in structure I (2.398(4) and

2.397(4) Å) are noticeably shorter than these distances

in tetraphenylantimony tosylate molecule (II)

(2.588(4) Å) [1]. This can be explained by an increased

electron density on this bond due to more pronounced

electron-donating ability of the (MeC₆H₄)₄Sb substitu-

ent as compared to that of the Ph₄Sb group. The above

facts are conﬁrmed by a decrease in the equatorial and

axial Sb–C bond lengths in structure I (2.098(5),

2.100(5), 2.120(5), 2.147(5) Å for molecule Ia and

2.092(5), 2.099(5), 2.127(5), 2.153(5) Å for molecule

Ib) with respect to the relevant bond lengths in struc-

ture II (2.099(4) 2.101(4), 2.119(4), and 2.129(4) Å)

and by a decrease in the C_axSbC_eqangles determining

the ionicity of the Sb–O bond (96.8(2)°, 98.8(2)°,

102.1(2)° in Ia; 96.7(2)°, 98.5(2)°, 102.2(2)° in Ib) as

compared ton the corresponding angles in structure II

(98.0(2)°, 101.3(2)°, 102.0(2)°). Note that in the acid

tetra-p-tolylantimony phthalate [5], bond lengths and

sites with the occupancy factors 0.7 and 0.3, while in

the structure of this compound described in [3], four

carbon atoms of one tolyl ligand are disordered over

two sites with the occupancy factor 0.5.

EXPERIMENTAL

Synthesis of I. A mixture of 1.00 g of penta-p-tolyl-

antimony, 1.43 g of tri-p-tolylbismuth bis(4-methyl-

benzenesulfonate), and 15 ml of toluene was allowed to

stand at 90–100°ë for 1 h. The solvent was removed;

two products were isolated after fractional recrystalli-

zation from a benzene–heptane (2 : 1) mixture. The

yield of compound I was 1.14 g (77%), mp 143°C; the

yield of tetraphenylbismuth 4-methylbenzenesulfonate

was 0.88 g (68%), mp 153°C.

X-ray diffraction analysis of the naturally faceted

single crystal was carried out on a SMART 1000 CCD

diffractometer (MoK_αradiation, graphite monochro-

mator, θ/2θ scan mode). The data were collected in sets

of 906, 660, and 350 scans at ϕ = 0°, 90°, and 180°,

respectively (ω scanning with the step of 0.2° and the

angles are also smaller than the corresponding parame- step counting time of 10 s). The crystal–detector dis-

ters in the acid tetraphenylantimony phthalate [4]. The tance was 45 mm. Correction for absorption of X-rays

RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 29 No. 5 2003

316

SHARUTIN et al.

by the sample was calculated from intensities of equiv-

alent reﬂections.

ACKNOWLEDGMENTS

The license to use the Cambridge Structural Data-

base was supported by the Russian Foundation for

Basic Research, project no. 99-07-90133.

The structure was solved by direct methods and

reﬁned by the least-squares method in an anisotropic

approximation for non-hydrogen atoms. The ë(2‡),

ë(3‡), ë(5‡), ë(6‡) and ë(52b), ë(53b), ë(55b),

ë(56b) atoms occupy their positions with the occu-

pancy factors 0.7 and 0.3, respectively.

REFERENCES

1. Sharutin, V.V., Sharutina, O.K., Panova, L.P., and

Bel’skii, V.K., Zh. Obshch. Khim., 1997, vol. 67, no. 9,

p. 1531.

2. Sharutin, V.V., Sharutina, O.K., Platonova, T.P., et al.,

Zh. Obshch. Khim., 2000, vol. 70, no. 11, p.1932.

Positions of the H atoms were calculated geometri-

cally (with the exception for the hydrogen atoms of

methyl groups C(7) and C(57), which were not found

from the electron density difference map) and reﬁned in

the rider model.

3. Sharutin, V.V., Sharutina, O.K., Tarasova, T.A., et al., Zh.

Obshch. Khim., 1999, vol. 69, no. 12, p. 1979.

4. Sharutin, V.V., Sharutina, O.K., Mel’nikova, I.G., et al.,

Izv. Ross. Akad. Nauk, Ser. Khim., 1996, no. 8, p. 2082.

5. Sharutin, V.V., Sharutina, O.K., Pakusina, A.P., and

Bel’skii, V.K., Zh. Obshch. Khim., 1997, vol. 67, no. 9,

p. 1536.

6. SMART and SAINT-Plus. Versions 5.0. Data Collection

and Processing Software for the SMART System, Bruker

AXS Inc., Madison, WI, USA, 1998.

7. 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.

The data collection and processing and the reﬁne-

ment of the unit cell parameters were carried out using

the SMART and SAINT-Plus programs [6]. All the cal-

culations for the determination and reﬁnement of the

structure were performed using the SHELXTL/PC pro-

grams [7].

Selected crystallographic data and the results of

reﬁnement of structure I are presented in Table 1, coor-

dinates and thermal parameters of atoms are given in

Table 2, and main bond lengths and angles are listed in

Table 3.

RUSSIAN JOURNAL OF COORDINATION CHEMISTRY Vol. 29 No. 5 2003

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