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DOI: 10.14529/chem200104
SYNTHESIS AND STRUCTURE OF B/S(THIOPHENE-2-ALDOXIMATO)-TR/S(5-BROMO-2-METHOXYPHENYL)ANTIMONY
E.V. Artem'eva, [email protected]
South Ural State University, Chelyabinsk, Russian Federation
Synthesis of bis(thiophene-2-aldoximato)tris(5-bromo-2-methoxyphenyl)antimony (1) has been carried out by the oxidative addition reaction of tris(5-bromo-2-methoxyphenyl)antimony with thiophene-2-aldoxime in the presence of tert-butyl hydroperoxide with the 1:2 molar ratio of the reactants. The compound has been characterized by IR spectroscopy and X-ray diffraction analysis. According to the X-ray diffraction analysis data, in the crystal there are two types of crystallographically independent the molecules, geometrical parameters of which are slightly different. Coordination polyhedron of antimony atoms in a molecule is a distorted trigonal bipyramid. The sum of the CSbC angles equals 360°, the values of the individual angles differ from the theoretical 120° by no more than 8.6(8)°. The axial OSbO angle is 175.8(4)°. The OSbC angles vary within the range 85.8(6)°-97.6(6)°. The average value of the Sb-C bond lengths is 2.13(2) A. The Sb-O distances equal 2.08(1) A. The distances between the Sb atom and N atoms of the iminoxy groups are 2.80(2)-2.94(2) A. The distances between the N and O atoms do not depend on the distances between the Sb and N atoms; they are equal to 1.39(2)-1.43(2) A. In the molecules there are contacts between the Sb and O atoms of methoxy groups, the corresponding distances are within the range of 3.13(1)-3.23(1) A. The molecules in a crystal are connected by intermolecular hydrogen bonds between the aromatic H and Br (2.883 A), S (2.992 A) and N (2.715 A) atoms. In the molecules there are intramolecular short contacts between the iminoxy group O atom and S (2.72(1)-2.80(1) A), as well as the methoxy group O atom (2.93(2)-3.03(2) A).
Keywords: tris(5-bromo-2-methoxyphenyl)antimony, thiophene-2-aldoxime, oxidative addition, structure, X-ray diffraction analysis, IR spectroscopy.
Introduction
It is known that triarylantimony dioximates are biologically active compounds, having antibacterial, antifungal [1] and antitumor [2, 3] activity. Various triarylantimony dioximates Ar3SbX2 (Ar = Ph, p-Tol, o-Tol, m-Tol, 3-F-C6H4, 4-F-C6H4; X = ONCHR, ONCRR') were obtained by substitution [1, 2, 4-7] and oxidative addition reactions, with the molar ratio of triaryl antimony and oxime 1:2 [8-18]. Synthesis of tris(5-bromo-2-methoxyphenyl)antimony oximates has been described in a few papers only [17-19]. Obviously, such compounds have not been studied enough, and a further investigation is required.
The present work concerns the study of the interaction of tris (5-bromo-2-methoxyphenyl)antimony with thiophene-2-aldoxime in the presence of tert-butyl hydroperoxide at 1:2:1 molar ratio of the reactants, and the structure determination of the reaction product.
Experimental
Synthesis of 6/s(thiophene-2-aldoximato)ira(5-bromo-2-methoxyphenyl)antimony (1).
77ris(5-bromo-2-methoxyphenyl)antimony (0.1 g, 0.14 mmol) and thiophene-2-aldoxime (0.037 g, 0.29 mmol) were dissolved in 10 ml of diethyl ether, then 70 % aqueous solution of tert-butyl hydroperoxide (0.019 g, 0.14 mmol) was added. The mixture was kept for 24 h at 20 °C. After the solvent evaporation, the solid residue was recrystallized from amyl acetate. 0.151 g (97 %) of colorless crystals of 1 with MP 136 °C was obtained.
IR spectrum, v, cm-1: 3438, 3096, 3065, 3003, 2961, 2932, 2837, 1572, 1472, 1437, 1420, 1375, 1351, 1283, 1269, 1254, 1209, 1180, 1144, 1092, 1049, 1016, 912, 862, 823, 808, 741, 711, 667, 619, 602, 555, 525, 467, 436.
Found, %: C 39.94, H 2.81. For C62H52 Br6N4O10S4Sb2 calculated, %: C 40.00, H 2.75.
IR spectra of compound 1 were recorded on a Shimadzu IRAffinity-1S FTIR-spectrometer; samples were prepared by pelletting with KBr (absorption region 4000-400 cm-1).
X-ray diffraction analysis of crystalline substance 1 was performed on a Bruker D8 QUEST automatic four-circle diffractometer (Mo Ka-emission, X 0.71073 A, graphite monochromator).
Data collection and editing, unit-cell parameters refinement, and correction for absorption were carried out in SMART and SAINT-Plus software [20]. All calculations aimed at solving and refining the structure of compound 1 were performed in SHELXL/PC [21] and OLEX2 software [22]. Structure 1 was determined by direct methods and refined with the least squares method in the anisotropic approximation for non-hydrogen atoms. Selected bond lengths and bond angles of 1 are summarized in Table 1.
Crystal Data for C62H52N4OioBr6Sb2S4 (M 1864.28 g/mol): triclinic, space group Pi, a 9.565(10) A, b 17.472(18) A, c 24.42(3) A, a 97.25(7)°, p 92.12(8)°, y 98.46(6)°, V3999(8) A3, Z 2, ^Mo 3.827 mm"1, Dcalc 1.548 g/cm3, 29317 reflections measured, 5456 unique reflections (Rint 0.0522), the number of refinement variables 800, GOOF 1.118, R factors for F2 > 2c(F2): Rj 0.0580, wR2 0.1635, R factors for all reflections R1 0.0680, wR2 0.1700.
The full tables of atomic coordinates, bond lengths, and bond angles were deposited with the Cambridge Crystallographic Data Centre (CCDC 1901674 for compound 1; [email protected]; http: //www.ccdc.cam .ac .uk).
Table 1
Selected bond lengths and bond angles in structure 1
a
Bond d, Â Angle ra, deg Angle ra, deg
Sb(1)-C(1) 2.15(2) O(4)Sb(1)O(5) 175.8(4) O(4)Sb(1)C(11) 87.3(6)
Sb(1)-C(11) 2.14(2) C(1)Sb(1)C(11) 120.6(7) O(4)Sb(1)C(21) 85.8(6)
Sb(1)-C(21) 2.11(2) C(1)Sb(1)C(21) 112.5(7) O(5)Sb(1)C(1) 86.1(6)
Sb(1)-O(4) 2.08(1) C(11)Sb(1)C(21) 126.9(7) O(5)Sb(1)C(11) 92.7(6)
Sb(1)-O(5) 2.08(1) O(4)Sb(1)C(1) 97.6(6) O(6)Sb(1)C(21) 90.8(6)
N(1)-C(35) 1.30(3) O(4)N(1)C(35) 110(1)
N(2)-C(45) 1.28(3) O(5)N(2)C(45) 113(2)
b
Sb(2)-C(51) 2.16(2) O(I)Sb(2)O(J) 175.2(5) O(I)Sb(2)C(61) 87.8(6)
Sb(2)-C(61) 2.12(2) C(51)Sb(2)C(61) 125.9(8) O(I)Sb(2)C(71) 85.2(6)
Sb(2)-C(71) 2.13(2) C(51)Sb(2)C(71) 122.5(7) O(J)Sb(2)C(51) 89.4(6)
Sb(2)-O(I) 2.10(1) C(71)Sb(2)C(81) 111.4(8) O(J)Sb(2)C(61) 87.6(6)
Sb(2)-O(J) 2.04(1) O(I)Sb(2)C(51) 92.2(6) O(J)Sb(2)C(71) 97.7(6)
N(3)-C(85) 1.23(3) O(I)N(3)C(85) 112(2)
N(4)-C(95) 1.21(4) O(J)N(4)C(95) 113(2)
Results and Discussion
It has been found that the oxidative addition reaction of trà(5-bromo-2-methoxyphenyl)antimony with thiophene-2-aldoxime in the presence of tert-butyl hydroperoxide at 1:2:1 molar ratio goes by a standard pathway with the formation of triarylantimony dioximate:
NOH + f-BuOOH
SbON
BuOH + H20
1
Compound 1 is a crystalline substance, highly soluble in aromatic hydrocarbons, resistant to moisture and air oxygen.
Structure 1 has been determined by X-ray diffraction analysis and confirmed by IR spectroscopy. In the IR spectrum of compound 1, there are absorption bands at 2932 cm-1 (thiophene C-H, st), 708, 712 cm-1 (thiophene C-H, S). Characteristic bands are observed at 1472 cm-1 (C=N bond),
1375 cm-1 (OH, 5), 912 cm-1 (N-O) [23]. Vibrations at 436 cm-1 indicate the presence of the Sb-C bond in the molecule of compound 1 [24]. The absorption bands at 1180 cm-1 and 1283 cm-1 correspond to vibrations of the CAr-Br and CAr-OMe bonds, respectively [23].
According to X-ray diffraction data, in crystal 1 there are two types of crystallographically independent molecules a and b, the geometric parameters of which are equal within the error limits, therefore, in the following, we discuss the structural data of molecule 1 a. The antimony atoms have a distorted trigonal-bipyramidal coordination with oxygen atoms in axial positions (Fig. 1). The SbC3 fragment lying in the equatorial plane is almost flat. The Sb atom deviates from the [C3] plane toward the axial oxygen atom by 0.001 A (a) and 0.053 A (b). The sum of the CSbC equatorial angles is 360° for both molecules, the values of the individual angles differ from the theoretical 120° by no more than 8.6(8)°. The axial OSbO angle is 175.8(4)°. The OSbC angles vary within the ranges 85.8(6)°-97.6(6)°. The NOON torsion angles accept large values (140(1)° (a), 117(1)° (b)) because Sb interacts with N from different sides. The angles between SbON planes equal 40.54° (a), 63.42° (b).
The average values of the Sb-C bond lengths are 2.13(2) A (a) and 2.14(2) (b) A. The Sb-O distances equal 2.08(1) A what is approximately equal to the sum of covalent radii of Sb and O atoms (2.07(1) A). The Sb -N distances between the Sb atom and N atoms of iminoxy groups (2.80(2), 2.94(2) A (a), 2.82(2) A (b)) are considerably less than the sum of Van der Waals radii of the Sb and N atoms (3.8 A [25]). The N-O distances do not depend on Sb- • N distances and are equal to 1.43(2) A (a) and 1.39(2), 1.41(2) A (b). The geometrical parameters of 1 are close to the ones for bis(thiophene-2-aldoximato)tri(o-tolyl)antimony [12]. The average values for N-O (1.41 A) and N-C (1.26(4) A) distances, as well as ONC angles (112(2)°) in 1 are close to the ones for thiophene-2-aldehyde (1.394(3) A, 1.269(8) A, 111.6(3)°) as well [12].
Fig. 1. Structure 1a showing thermal ellipsoids at 30% probability.
Hydrogen atoms have been omitted for clarity
In molecule 1 there are contacts Sb(1,2)---OMe, the corresponding distances equal 3.18(1)-3.23(1) (a), 3.13(1)-3.23(1) À (b).
Molecules a and b in crystal 1 are linked by intermolecular contacts HAr-• Br (2.883 À) and HMe-••S (2.992 À) (Fig. 2). Molecules of b type are connected via HAr---N interactions (2.715 À). In the molecules there are such intramolecular short contacts as S--O (2.80(1) À (a), 2.72(1), 2.74(1) À (b)), OMeo ••O (2.97(2), 2.93(2) À (a), 3.03(2), 2.93(2), 2.79(2) À (b)).
Fig. 2. The intermolecular interactions in 1
Conclusion
The oxidative addition reaction of tris(5-bromo-2-methoxyphenyl)antimony with thiophene-2-aldoxime at 1:2 molar ratio leads to formation of tris(5-bromo-2-methoxyphenyl)antimony dioximate, the structural organization of which is due to hydrogen bonds and other short contacts.
Acknowledgments
We are grateful to V.V. Sharutin for the X-ray diffraction analysis of 1 and O.K. Sharutina for the article preparation to submission.
References
1. Bajpai K., Srivastava R.C. Synthesis and Reactions of O-triorganoantimony Dioximates. Synth. Inorg. Met.-Org. Chem, 1981, vol. 11, no. 1, pp. 7-13. DOI: 10.1080/00945718108059270.
2. Yin H., Quan L., Li L. Synthesis, Spectroscopic and Structural Aspects of Triphenylantimo-ny(V) Complex with Internally Functionalized Acetylferroceneoxime: Crystal and Molecular Structures of [C5H5FeC5H4C(CH3)=NO]2SbPh3 and C5H5FeC5H4C(CH3)=NOH. Inorg. Chem. Com., 2008, no. 11, pp. 1121-1124. DOI: 10.1016/j.inoche.2008.06.017.
3. Sharma P., Perez D., Cabrera A., Rosas N., Arias J.L. Perspectives of Antimony Compounds in Oncology. Acta Pharm. Sinica, 2008, vol. 29, no. 8, pp. 881-890. DOI: 10.1111/j.1745-7254.2008.00818.x.
4. Gupta A., Sharma R.K., Bohra R., Jain V.K., Drake J.E., Hursthouse M.B., Light M.E. Synthetic, Spectroscopic and Structural Aspects of Triphenylantimony(V) Complexes with Internally Functionalized Oximes: Crystal and Molecular Structure of [Ph3Sb{ON=C(Me)C5HN-2} 2]. Polyhedron, 2002, vol. 21, no. 23, pp. 2387-2392. DOI: 10.1016/S0277-5387(02)01155-5.
5. Gupta A., Sharma R.K., Bohra R., Jain V.K., Drake J.E., Hursthouse M.B., Light M.E. Triorga-noantimony(V) Complexes with Internally Functionalized Oxsimes: Syntetic, Spectroscopic and Structural Aspects of [R3Sb(Br)L],[R3Sb(OH)L],and [R3SbL2], Crustal and Molecular Structures of [Me3Sb{ON=C(Me)C4H3O}2],[Me3Sb{ON=C(Me)C4H3S}2], 2-OC4^C(Me)=NOH and 2-SC4H3C(Me)=NOH. J. Organometal. Chem, 2002, vol. 645, no. 2, pp. 118-126. DOI: 10.1016/S0022-328X(01)01338-9.
6. Jain V.K., Bohra R., Mehrotra R.C. Synthesis and Spectroscopic Studies of Trialkyl Bis(iminoxy)stibines. Inorg. Chim. Acta, 1981, vol. 51, pp. 191-194. DOI: 10.1016/S0020-1693(00)88338-3.
7. Dong L., Yin H., L. Wen, Wang D. Bis(2-hydroxybenzaldehyde Oximato-KO)triphenylanti-mony(V). Acta Crystallogr., 2009, vol. 65E, no. 11, pp. m1438. DOI: 10.1107/S1600536809043542.
8. Dodonov V.A., Gushhin A.V., Gor'kaev D.A., Fukin G.K., Starostina T.I., Zaharov L.N., Kurs-kij Ju.A., Shavyrin A.S. Synthesis and Structure of Triphenylantimony Oximates. Russ. Chem. Bull., 2002, no. 6, pp. 1051-1057. DOI: 10.1023/A:1019634307064.
9. Sharutin V.V., Sharutina O.K., Efremov A.N. Syntheses and Structures of Tris(para-tolyl)-, Tris(3-fluorophenyl)-, and Tris(4-fluorophenyl)antimony Dioximates. Coord Chem, 2017, vol. 43, no. 8, pp. 526-534. DOI: 10.1134/S1070328417080073.
10. Sharutin V.V., Sharutina O.K., Molokova O.V., Pakusina A.P., Gerasimenko A.V., Gerasi-menko E.A. Synthesis and Structure of Triphenylantimony Bis(acetophenoneoximate). Rus. J. Coord. Chem, 2002, vol. 28, no. 7, pp. 464-467. DOI: 10.1023/A: 1016293009968.
11. Sharutin V.V., Sharutina O.K., Molokova O.V., Pakusina A.P., Gerasimenko A.V., Sergien-ko A.S., Bukvetskij B.V., Popov D.Yu. Synthesis and Structures of Tetra- and Triarylantimony Oximates. Rus. J. Coord. Chem, 2002, vol. 28, no. 8, pp. 544-553. DOI: 10.1023/A:1019701511840.
12. Sharutin V.V., Sharutina O.K., Artem'eva E.V., Makerova M.S. Synthesis and Structure of Tri(o-tolyl)antimony Dioximates. Rus. J. Gen. Chem., 2016, vol. 86, no. 12, pp. 2671-2676. DOI: 10.1134/S1070363216120161.
13. Sharutin V.V., Sharutina O.K., Efremov A.N. Synthesis and Structure of Triarylantimony Oximates: (3-FC6H4)3Sb[ON=CHC6H4(Br-2)]2 and p-Tol3Sb(ON=CHC4H3O)2 • PhH. Butlerov Commun, 2016, vol. 47, no. 8, pp. 145-149.
14. Sharutin V.V., Sharutina O.K., Gabitova D.M., Shaikhvaleeva S.Ya. Triphenylantimony Dioximates Ph3Sb(ON=CHR)2 (R = C6H4NO2-2, C6H4NO2-3, C6H4Br-2, C6^Br-3, or C4H2ONO2-5): Synthesis and Structure. Rus. J. Inorg. Chem, 2017, vol. 62, no. 1, pp. 55-62. DOI: 10.1134/S003602361701017X.
15. Sharutin V.V., Molokova O.V., Sharutina O.K., Gerasimenko A.V., Pushilin M.A. Synthesis and Structure of Triarylantimony Dioximates. Rus. J. Gen. Chem., 2004, vol. 74, no. 10, pp. 1485-1491. DOI: 10.1007/s11176-005-0041-4.
16. Sharutin V.V., Sharutina O.K., Molokova O.V. Synthesis and Structure of Tetra- and Triphenylantimony Salicylaldoximates. Rus. J. Inorg. Chem., 2012, vol. 57, no. 6, pp. 832-837. DOI: 10.1134/S0036023612010226.
17. Sharutin V.V., Sharutina O.K. Specific Features of the Reaction between Tris(5-bromo-2-methoxyphenyl)antimony and 2-Oxybenzaldoxime: Structure of Bis(^3-2-oxybenzaldoximato-O,O',N)-(^2-oxo)-bis(5-bromo-2-methoxyphenyl)diantimony. Rus. J. Inorg. Chem., 2014, vol. 59, no. 11, pp. 1263-1267. DOI: 10.1134/S0036023614110229.
18. Artem'eva E.V., Sharutin V.V., Sharutina O.K. Complexes Ar3Sb(ONCHC6HNO2-2)2 • 0.5C6H6, Ar3Sb(ONCHC6HNO2-3)2 • 20^5 and A^Sb(OC(O)CH2C6H4F-3)2 (Ar = C6^OMe-2-Br-5): Synthesis and Structure. Rus. J. Inorg. Chem, 2019, vol. 64, no. 11, pp. 1410-1417. DOI: 10.1134/S0036023619110032.
19. Artem'eva E.V., Sharutina O.K. Synthesis and Structure of Tetraphenylantimony p-Isatoximate. SUSUBulletin. Ser: Chem, 2018, vol. 10, no. 1, pp. 48-54. DOI: 10.14529/chem180106.
20. Bruker (2000) SMART. Bruker Molecular Analysis Research Tool, Versions 5.625, Bruker AXS, Madison, Wisconsin, USA.
21. Bruker (2000) SAINTPlus Data Reduction and Correction Program, Versions 6.02a, Bruker AXS, Madison, Wisconsin, USA.
22. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H. OLEX2: Complete Structure Solution, Refinement and Analysis Program. J. Appl. Cryst, 2009, vol. 42, pp. 339-341. DOI: 10.1107/S0021889808042726.
23. Pretsch E., Clerc T., Seibl J., Simon W. Tables of Spectral Data for Structure Determination of Organic Compounds. Springer Science & Business Media, 2013. P. 1735.
24. Doak G.O., Long G.G., Freedman L.D. The Infrared Spectra of Some Phenylsubstituted Penta-valent Antimony Compounds. J. Organomet. Chem, 1965, vol. 4, no. 1, pp. 82-91.
25. Batsanov S.S. [Atomic Radii of the Elements]. Rus. J. Inorg. Chem., 1991, vol. 36, no. 12, pp. 3015-3037. (in Russ.)
Received 9 December 2019
УДК 546.86+547.53.024+548.312.5 DOI: 10.14529/chem200104
СИНТЕЗ И СТРОЕНИЕ БИС(ТИОФЕН-2-АЛЬДОКСИМАТО)7РИС(5-БРОМ-2-МЕТОКСИФЕНИЛ)СУРЬМЫ
Е.В. Артемьева
Южно-Уральский государственный университет, г. Челябинск, Россия
По реакции окислительного присоединения трис(5-бром-2-метоксифенил)сурьмы с тиофен-2-альдоксимом в присутствии трет-бутилгидропероксида при соотношении реагентов 1:2 синтезирована бис[(тиофен-2-альдоксимато)трис(5-бром-2-метоксифенил)сурьма] (1). Соединение охарактеризовано методами ИК-спектроскопии и рентгеноструктурного анализа. Согласно данным рентгеноструктурного анализа, в кристалле находятся два типа кристаллографически независимых молекул, геометрические параметры которых незначительно отличаются. Координационный полиэдр атомов сурьмы в молекуле - тригональная бипирамида. Сумма углов CSbC составляет 360°, при этом значения индивидуальных углов отличаются от теоретического 120° не больше, чем на 8,6(8)°. Аксиальные углы OSbO равны 175,8(4)°. Углы OSbC варьируют в пределах 85,8(6)°-97,6(6)°. Средние значения длин связей Sb-C составляют 2,13(2) А. Расстояния Sb-O равны 2,08(1) А. Расстояния между атомами Sb и атомами N иминокси-групп составляют 2,80(2)-2,94(2) А. Расстояния между атомами N и O не зависят от расстояний между атомами Sb и N и равны 1,39(2)-1,43(2) А. В молекулах имеют место контакты между атомами Sb и атомами O метокси-групп, соответствующие расстояния лежат в пределах 3,13(1)-3,23(1) А. Молекулы в кристаллах связаны межмолекулярными водородными связями между атомами H и Br (2,883 А), S (2,992 А) и N (2,715 А). В молекулах присутствуют короткие контакты между атомом O иминокси-групп и атомами S (2,72(1)-2,80(1) А), а также атомами O метокси-групп (2,93(2)-3,03(2) А).
Ключевые слова: трис(5-бром-2-метоксифенил)сурьма, тиофен-2-альдоксим, окислительное присоединение, строение, рентгеноструктурный анализ, ИК-спектроскопия.
Литература
1. Bajpai, K. Synthesis and Reactions of o-Triorganoantimony Dioximates / K. Bajpai, R.C. Srivastava // Synth. Inorg. Met. - Org. Chem. - 1981. - V. 11, № 1. - P. 7-13.
2. Yin, H. Synthesis, Spectroscopic and Structural Aspects of Triphenylantimony(V) Complex with Iinternally Functionalized Acetylferroceneoxime: Crystal and Molecular Structures of [CsH5FeC5H4C(CH3)=NO]2SbPh3 and CsHsFeCsH^C^bNOH / H. Yin, L. Quan, L. Li // Inorg. Chem. Com. - 2008. - № 11. - P. 1121-1124.
3. Perspectives of Antimony Compounds in Oncology / P. Sharma, D. Perez, A. Cabrera et al. // Acta Pharm. Sinica, - 2008. - V. 29, № 8. - P. 881-890. DOI: 10.1111/j.1745-7254.2008.00818.x.
4. Gupta, A. Synthetic, Spectroscopic and Structural Aspects of Triphenylantimony(V) Complexes with Internally Functionalized Oximes: Crystal and Molecular Structure of [Ph3Sb{ON=C(Me)C5H4N-2}2] / A. Gupta, R.K. Sharma, R. Bohra // Polyhedron. - 2002. - V. 21, № 23. - P. 2387-2392. DOI: 10.1016/S0277-5387(02)01155-5.
5. Triorganoantimony(V) Complexes with Internally Functionalized Oximes: Syntetic, Spectroscopic and Structural Aspects [R3Sb(Br)L],[R3Sb(OH)L],and [R3SbL2], Cristal and Molecular Structures of [Me3Sb{ON=C(Me)C4H3O}2],[Me3Sb{ON=C(Me)C4H3S}2], 2-OC4ftC(Me)=NOH and 2-SC4H3C(Me)=NOH / A. Gupta, R.K. Sharma, R. Bohra et al. // J. Organometal. Chem. - 2002. - V. 645, № 2. - P. 118-126. DOI: 10.1016/S0022-328X(01)01338-9.
6. Jain, V.K. Synthesis and Spectroscopic Studies of Trialkyl 5/5(iminoxy)stibines. / V.K. Jain, R. Bohra, R.C. Mehrotra // Inorg. Chim. Acta. - 1981. - V. 51. - P. 191-194. DOI: 10.1016/S0020-1693(00)88338-3.
7. 57s(2-hydroxybenzaldehyde Oximato-KO)triphenylantimony(V) / L. Dong, H. Yin, Wen L., D. Wang // Acta Crystallogr. - 2009. - V. 65E, № 11. - P. m1438. DOI: 10.1107/S1600536809043542.
8. Синтез и строение оксиматов трифенилсурьмы / В.А. Додонов, А.В. Гущин, Д.А. Горька-ев и др. // Изв. РАН. Сер. хим. - 2002. - № 6. - С. 965-971.
9. Шарутин, В.В. Синтез и строение диоксиматов трис(пара-толил)-, трис(3-фторфенил)-и трис(4-фторфенил)сурьмы / В.В. Шарутин, О.К. Шарутина, А.Н. Ефремов // Коорд. Хим. -2017. - Т. 43, № 8. - С. 496-504. DOI: 10.7868/S0132344X17080072.
10. Синтез и строение бис(ацетофеноноксимата) трифенилсурьмы / В.В. Шарутин, О.К. Ша-рутина, О.В. Молокова и др. // Коорд. Хим. - 2002. - Т. 28, № 7. - С. 497-501.
11. Синтез и строение оксиматов тетра- и триарилсурьмы / В.В. Шарутин, О.К. Шарутина, О.В. Молокова и др. // Коорд. Хим. - 2002. - Т. 28, № 8. - С. 581-590.
12. Синтез и строение диоксиматов три(о-толил)сурьмы / В.В. Шарутин, О.К. Шарутина, Е В. Артемьева, М.С. Макерова // Журн. общ. химии. - 2016. - Т. 86, № 12. - С. 2039-2044.
13. Шарутин, В.В. Синтез и строение диоксиматов триарилсурьмы (3-FC6H4)3Sb[ON=CHC6H4(Br-2)b и p-TobSb(ON=CHC4H3O)2 • PhH / В.В. Шарутин, О.К. Шарутина, А Н. Ефремов // Бутлер. сообщ. - 2016. - Т. 47, № 8. - С. 145-149.
14. Синтез и строение диоксиматов трифенилсурьмы Ph3Sb(ON=CHR)2 (R = C6HNO2-2, C6H4NO2-3, СбН^г-2, СбНЗг-3, or C4H2ONO2-5) / В.В. Шарутин, О.К. Шарутина, ДМ. Габитова, С.Я. Шайхвалеева // Журн. неорган. химии. - 2017. - Т. 62, № 1. - С. 61-68. DOI: 10.7868/S0044457X17010172.
15. Синтез и строение диоксиматов триарилсурьмы / В.В. Шарутин, О.В. Молокова, О.К. Шарутина и др. // Журн. общ. химии. - 2004. - Т. 74, Вып. 10. - С. 1600-1607.
16. Шарутин, В.В. Синтез и строение салицилальдоксиматов тетра- и трифенилсурьмы /
B.В. Шарутин, О.К. Шарутина, О.В. Молокова // Журн. неорган. химии. - 2012. - Т. 57, № 6. -
C. 902-907.
17. Шарутин, В.В. Особенности взаимодействия трис(5-бром-2-метоксифенил)сурьмы с 2-оксибензальдоксимом. Строение бис^^-оксибензальдоксимато-О^'^КН^-оксо^бис^-бром^-метоксифенил)дисурьмы / В.В. Шарутин, О.К. Шарутина // Журн. неорган. химии. - 2014. -Т. 59., № 11. - С. 1507-1511. DOI: 10.7868/S0044457X14110221.
18. Артемьева, Е.В. Синтез и строение комплексов Ar3Sb(ONCHC6H4NO2-2)2 • 0.5C6H6, Ar3Sb(ONCHC6HNO2-3)2 • 2С<Н и Ar3Sb(OC(O)CH2C6H4F-3)2 (Ar = C6^OMe-2-Br-5) / Е.В. Артемьева, В.В. Шарутин, О.К. Шарутина // Журн. неорган. химии. - 2019. - Т. 64, № 11. - С. 11841190. DOI: 10.1134/S0044457X19110035.
19. Артемьева, Е.В. Синтез и строение Р-изатоксимата тетрафенилсурьмы / Е.В. Артемьева, О.К. Шарутина // Вестник ЮУрГУ. Серия: Химия. - 2018. - Т. 10, № 1. - С. 48-54. DOI: 10.14529/chem180106.
20. Bruker (2000) SMART. Bruker molecular analysis research tool, versions 5.625 Bruker AXS, Madison, Wisconsin, USA.
21. Bruker (2000) SAINTPlus data reduction and correction program, versions 6.02a, Bruker AXS, Madison, Wisconsin, USA.
22. OLEX2: Complete structure solution, refinement and analysis program / O.V. Dolomanov, L.J. Bourhis, R.J. Gildea et al. // J. Appl. Cryst. - 2009. - V. 42. - P. 339-341. DOI: 10.1107/S0021889808042726.
23. Преч, Э. Определение строения органических соединений (Таблицы спектральных данных) / Э. Преч, Ф. Бюльманн, К. Аффольтер. - М.: Мир; БИНОМ. Лаборатория знаний, 2006. - 1735 с.
24. Doak, G.O. The infrared spectra of some phenylsubstituted pentavalent antimony compounds / G O. Doak, G.G. Long, L.D. Freedman // J. Organomet. Chem. - 1965. - V. 4, № 1. - P. 82-91.
25. Бацанов, С.С. Атомные радиусы элементов / С.С. Бацанов // Журн. неорган. химии. -1991. - Т. 36, № 12. - С. 3015-3037.
Артемьева Екатерина Владимировна - аспирант химического факультета, ЮжноУральский государственный университет. 454080, г. Челябинск, проспект Ленина, 76. E-mail: katriona-art@yandex .ru.
Поступила в редакцию 9 декабря 2019 г.
ОБРАЗЕЦ ЦИТИРОВАНИЯ
Artem'eva, E.V. Synthesis and Structure of B/s(thiophene-2-aldoximato)-frw(5-bromo-2-methoxy-phenyl)antimony / E.V. Artem'eva // Вестник ЮУрГУ. Серия «Химия». - 2020. - Т. 12, № 1. - С. 35-41. DOI: 10.14529/chem200104
FOR CITATION
Artem'eva E.V. Synthesis and Structure of Bis(thiophene-2-aldoximato)-tris(5-bromo-2-methoxy-phenyl)antimony. Bulletin of the South Ural State University. Ser. Chemistry. 2020, vol. 12, no. 1, pp. 35-41. (in Russ.). DOI: 10.14529/chem200104
