Structural Features of Pentaphenyl Antimony, Penta(para-tolyl)antimony, and their Solvates with Organic Solvents
Keywords:
pentaphenylantimony, penta(para-tolyl)antimony, solvate, benzene, dioxane, structure, X-ray structural analysisAbstract
The structures of pentaphenylantimony, penta(para-tolyl)antimony, as well as their solvates with benzene, dioxane, tetrahydrofuran, and xylene were determined by X-ray diffraction analysis. According to the X-ray diffraction analysis carried out at 293 K on an automatic four-circle D8 Quest Bruker diffractometer (two-coordinate CCD detector, MoKα radiation, λ = 0.71073 Å, graphite monochromator) in pentaphenylantimony crystals Ph5Sb (1) [C30H25Sb, M 507.25; triclinic system, P-1 symmetry group; cell parameters: a = 10.286(3), b = 10.510(4), c = 13.590(4) Å; = 68.29(2), β = 79.364(14), = 61.272(12); V = 1196.9(7) Å3; Z 2; crystal size 0.5 0.38 0.29 mm; reflection index intervals –21 ≤ h ≤ 21, –21 ≤ k ≤ 21, –28 ≤ l ≤ 28; total reflections 177843; independent reflections 22858; Rint 0.0446; GOOF 1.067; R1 = 0.0440, wR2 = 0.0848; residual electron density 1.09/–0.86 e/Å3, solvate of pentaphenylantimony with benzene Ph5Sb ∙ 0.5PhH (2) [C66H56Sb2, M 1092.61; triclinic system, P-1 symmetry group; cell parameters: a = 13.165(11), b = 14.394(16), c = 15.193(13) Å; = 90.22(3), β = 113.71(2), = 94.23(5); V = 2627(4) Å3; Z 2; crystal size 0.49 x 0.38 x 0.33 mm; reflection index intervals –16 ≤ h ≤ 16, –18 ≤ k ≤ 18, –19 ≤ l ≤ 19; total reflections 61668; independent reflections 11757; Rint 0.0395; GOOF 1.022; R1 = 0.0270, wR2 = 0.0585; residual electron density 0.43/–0.63 e/Å3, solvate of pentaphenylantimony with dioxane Ph5Sb ∙ 0,5C4H8O2 (3) [C32H29OSb, M 551.30; triclinic system, P–1 symmetry group; cell parameters: a = 10.451(5), b = 10.462(4), c = 13.323(5) Å; = 75.647(11), β = 69.648(19), = 86.300(19); V = 1322.8(9) Å3; Z 2; crystal size 0.43 0.35 0.27 mm; reflection index intervals –18 ≤ h ≤ 18, –18 ≤ k ≤ 18, –23 ≤ l ≤ 23; total reflections 99009; independent reflections 15054; Rint 0.0505; GOOF 1.036; R1 = 0.0554, wR2 = 0.1038; residual electron density 1.04/–0.58 e/Å3, penta(para-tolyl)antimony p-Tol5Sb (4) [C35H35Sb, M 577.38; monoclinic system, P21/n symmetry group; cell parameters: a = 14.472(6), b = 12.084(7), c = 17.009(6) Å; β = 102.934(14); V = 2899(2) Å3; Z 4; crystal size 0.38 0.26 0.24 mm; reflection index intervals –19 ≤ h ≤ 19, –16 ≤ k ≤ 16, –22 ≤ l ≤ 22; total reflections 106229; independent reflections 7238; Rint 0,0296; GOOF 1.081; R1 = 0.0239, wR2 = 0.0548; residual electron density 0.59/–0.69 e/Å3. Complete tables of atomic coordinates, bond lengths, and bond angles for the structure have been deposited with the Cambridge Crystallographic Data Center (Nos. 2124594 (1), 2121835 (2), 2124972 (3), 2124962 (4); deposit@ccdc.cam.ac). uk; https://www.ccdc.cam.ac.uk).References
Cambridge Crystallographic Data Center. 2020. deposit@ccdc.cam.ac.uk; http://www.ccdc.cam.ac.uk
Wittig, G. Pentaphenylarsen und Pentaphenylantimon / G. Wittig, K. Clauss // Ann. – 1952. – Bd. 577. – S. 26–39. DOI:10.1002/JLAC.19525770104
Wheatley, P.J. An X-ray Diffraction Determination of the Crystal and Molecular Structure of Pentaphenylantimony / P.J. Wheatley // J. Chem. Soc. – 1964. – P. 3718–3723. DOI: 10.1039/JR9640003718
Beauchamp, A.L. A Reinvestigation of the Crystal and Molecular Structure of Pentaphenylantimony / A.L. Beauchamp, M.J. Bennett, F.A. Cotton // J. Am. Chem. Soc. – 1968. – V. 90. – P. 6675–6680. DOI: 10.1021/ja01026a020.
Brabant, C. Structure Crystalline du Pentaphenylantimone Dans le Solvate Cycljhexanique (C6H5)5Sb ∙ ½ C6H12 / C. Brabant, B. Blanck, A.L. Beauchamp // J. Organomet. Chem. – 1974. – V. 82. – P. 231–234. DOI: 10.1016/S0022-328X(00)90360-7.
Geometry of Pentaphenylantiminy in Solution: Support for a Trigonal Bipyramidal Assignment from X-ray Absorption Spectroscopy and Vibrational Spectroscopic Data / B. Lindquist-Kleissler, M. Weng, P. Le Magueres, G.N. George, T.C. Johnstone // Inorg. Chem. – 2021. – V. 60. – P. 8566–8574. DOI: 10.1021/acs.inorgchem.1c00496.
Brabant, C. The Crystal and Molecular Structure of Penta-p-tolylantimony, (p-CH3C6H4)5Sb / C. Brabant, J. Hubert, A.L. Beauchamp // Can. J. Chem. – 1973. – V. 51. – P. 2952–2955. DOI: 10.1139/v73-439.
Schröder, G. Syntheses, Crystal and Solution Structures, Ligand-exchange and Ligand-coupling Reactions of Mixed Pentaarylantimony / G. Schröder, T. Okinaka, Y. Mimura et al. // Chem. -Eur. J. – 2007. – V. 13. – P. 2517–2529. DOI: 10.1002/chem.200601439
Шарутин, В.В. Синтез, реакции и строение арильных соединений пятивалентной сурьмы / В.В. Шарутин, А.И. Поддельский, О.К. Шарутина // Коорд. химия. – 2020. – Т. 46, № 10. – С. 579–648. DOI: 10.31857/S0132344X20100011.
Holmes, R.R. Structural Distortions of Cyclic Phosphoranes and the Berry Exchange Coordinate. A Quantitative Description / R.R. Holmes, J.A. Deiters // J. Amer. Chem. Soc. – 1977. – V. 99, № 10. – P. 3318–3326. DOI:10.1080/10426509508036945.
Brock, C.P. The Role of Coulombic Interactions in Explaining the Anomalous Structure of Penta¬phenylantimony / C.P. Brock // Acta Crystallogr. – 1977. – V. 33A, № 1. – P. 193–197. DOI: 10.1107/S0567739477000394.
Beattie, I.R. The Shape of Pentaphenylantimony and Pentaphenylarsenic in Solution / I.R. Beattie, K.M.S. Livingston // J. Chem. Soc. Dalton Trans. – 1972. – № 7. – P. 784–786. DOI: 10.1039/DT9720000784.
Covalent Radii Revisited / B. Cordero, V. Gómez, A.E. Platero-Prats et al. // Dalton Trans. – 2008. – Iss. 21. – P. 2832–2838. DOI: 10.1039/B801115J.
Consistent Van der Waals Radii for the Whole Main Group / M. Mantina, A.C. Chamberlin, R. Valero et al. // J. Phys. Chem. A. – 2009. – V. 113, iss. 19. – P. 5806–5812. DOI: 10.1021/jp8111556.
Structural Characterization of Some Novel Oxidation Products of Triphenylstibine / E.W.J. Grigsby, R.D. Hart, C.L. Raston, B.W. Skelton, A.H. White // Aust. J. Chem. – 1997. – V. 50, № 6. – P. 675–682. DOI: 10.1071/C96042.
Structure Analysis of Triaryl Derivatives of the Group V Elements. Crystal and Molecular Structure of Tri-p-tolylantimony, C21H21Sb / A.N. Sobolev, I.P. Romm, V.K. Belskii, E.N. Gur'yanova // J. Organomet. Chem. – 1979. – V. 179, № 2. – P. 153–157. DOI:10.1016/S0022-328X(00)95217-3.
Кристаллическая и молекулярная структура трис(4-N,N-диметиламинофенил)сурьмы / В.В. Шарутин, В.С. Сенчурин, О.К. Шарутина, О.В. Чагарова // Журн. неорган. химии. – 2012. – Т. 57, № 8. – С. 1149–1154.
2-Метокси-5-бромфенильные соединения сурьмы и висмута. Синтез и строение / В.В. Шарутин, В.С. Сенчурин, О.К. Шарутина, О.В. Чагарова // Журн. общ. химии. – 2011. – Т. 81, № 10. – С. 1649–1652.
Шарутин, В.В., Трис(2-метокси-5-хлорфенил)сурьма: синтез и реакции окислительного присоединения / В.В. Шарутин, О.К. Шарутина // Журн. общ. химии. – 2020. – Т. 90, № 10. – С. 1577–1582. DOI: 10.31857/S0044460X20100133.
Тарасевич, Б.Н. ИК-спектры основных классов органических соединений / Б.Н. Тарасе-вич. – М.: МГУ, 2012. – 54 с.
Инфракрасная спектроскопия органических и природных соединений: учебное пособие / А.В. Васильев, Е.В. Гриненко, А.О. Щукин и др. – СПб.: СПбГЛТА, 2007. – 54 с.
Spectral Database for Organic Compounds, SDBS. Release 2021. National Institute of Advanced Industrial Science and Technology.
Bruker. SMART and SAINT-Plus. Versions 5.0. Data Collection and Processing Software for the SMART System. Bruker AXS Inc., Madison, Wisconsin, USA, 1998.
Bruker. SHELXTL/PC. Versions 5.10. An Integrated System for Solving, Refining and Display-ing Crystal Structures From Diffraction Data. Bruker AXS Inc., Madison, Wisconsin, USA, 1998.
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.
