Home Physical Sciences Crystal structure of iodido-triphenyl-(triphenylphosphine oxide)tin(IV), C36H30IOPSn
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Crystal structure of iodido-triphenyl-(triphenylphosphine oxide)tin(IV), C36H30IOPSn

  • Kong Mun Lo , See Mun Lee and Edward R.T. Tiekink ORCID logo EMAIL logo
Published/Copyright: October 11, 2019

Abstract

C36H30IOPSn, monoclinic, P21 (no. 4), a = 9.7251(6) Å, b = 17.3609(11) Å, c = 10.0542(6) Å, β = 114.379(1)°, V = 1546.16(17) Å3, Z = 2, Rgt(F) = 0.0113, wRref(F2) = 0.0301, T = 296(2) K.

CCDC no.: 1953498

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow prism
Size:0.25 × 0.15 × 0.11 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.90 mm−1
Diffractometer, scan mode:Bruker SMART APEX, ω
θmax, completeness:28.3°, >99%
N(hkl)measured, N(hkl)unique, Rint:19627, 7642, 0.015
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 7603
N(param)refined:361
Programs:Bruker [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
I1−0.18870(2)0.38832(2)0.05116(2)0.01789(4)
Sn0.06869(2)0.46646(2)0.26278(2)0.01190(3)
P10.41973(6)0.52683(3)0.57287(5)0.01174(9)
O10.28159(17)0.53146(8)0.43105(15)0.0159(3)
C1−0.0002(2)0.57881(11)0.1729(2)0.0134(4)
C20.1057(2)0.63274(12)0.1717(2)0.0172(4)
H20.2078770.6204640.2139080.021*
C30.0596(3)0.70497(12)0.1077(2)0.0189(4)
H30.1309910.7399770.1054470.023*
C4−0.0915(3)0.72471(12)0.0477(2)0.0184(4)
H4−0.1219050.7728980.0052510.022*
C5−0.1982(2)0.67209(13)0.0510(2)0.0188(4)
H5−0.2997450.6855550.0131310.023*
C6−0.1525(2)0.59922(12)0.1113(2)0.0157(4)
H6−0.2244760.5637360.1104070.019*
C70.2293(2)0.40758(11)0.2079(2)0.0137(4)
C80.2589(3)0.43316(12)0.0904(2)0.0201(4)
H80.2052080.4746200.0344700.024*
C90.3677(3)0.39717(14)0.0569(3)0.0263(5)
H90.3867850.414805−0.0212310.032*
C100.4484(3)0.33520(13)0.1386(3)0.0239(5)
H100.5220260.3116470.1160830.029*
C110.4189(2)0.30838(13)0.2541(2)0.0207(4)
H110.4721120.2664320.3087090.025*
C120.3097(2)0.34435(12)0.2881(2)0.0169(4)
H120.2899620.3259860.3653680.020*
C130.0288(2)0.43000(12)0.4461(2)0.0145(4)
C140.0249(2)0.48489(12)0.5459(2)0.0171(4)
H140.0352430.5368090.5292500.021*
C150.0055(2)0.46269(15)0.6704(2)0.0210(4)
H150.0014740.4998110.7353920.025*
C16−0.0077(2)0.38541(15)0.6973(2)0.0223(4)
H16−0.0185380.3705650.7813660.027*
C17−0.0049(3)0.32990(13)0.5983(2)0.0216(4)
H17−0.0146140.2780160.6157260.026*
C180.0126(3)0.35237(12)0.4730(2)0.0191(4)
H180.0135090.3152520.4066570.023*
C190.3874(2)0.57723(11)0.7135(2)0.0139(4)
C200.4537(2)0.55538(12)0.8599(2)0.0172(4)
H200.5189330.5134370.8888880.021*
C210.4219(3)0.59649(14)0.9625(2)0.0232(5)
H210.4637790.5811821.0598460.028*
C220.3271(3)0.66081(14)0.9197(3)0.0258(5)
H220.3070090.6886280.9886930.031*
C230.2636(3)0.68299(13)0.7753(3)0.0250(5)
H230.2007580.7258600.7472140.030*
C240.2928(3)0.64181(12)0.6717(3)0.0196(4)
H240.2494520.6570630.5743260.024*
C250.5760(2)0.57320(11)0.5535(2)0.0148(4)
C260.6857(3)0.61284(13)0.6683(3)0.0226(5)
H260.6810890.6144690.7587680.027*
C270.8024(3)0.65006(14)0.6487(3)0.0278(5)
H270.8757300.6766350.7257570.033*
C280.8090(3)0.64737(13)0.5136(3)0.0265(5)
H280.8861080.6728760.4995630.032*
C290.7012(3)0.60682(15)0.3994(3)0.0268(5)
H290.7072610.6045020.3095910.032*
C300.5847(3)0.56979(13)0.4182(2)0.0210(4)
H300.5123510.5427330.3412360.025*
C310.4753(2)0.42993(11)0.6328(2)0.0146(4)
C320.5937(2)0.39505(13)0.6113(2)0.0172(4)
H320.6531350.4239390.5773330.021*
C330.6229(3)0.31698(13)0.6407(2)0.0196(4)
H330.7006550.2934580.6247920.023*
C340.5357(3)0.27412(13)0.6940(2)0.0209(4)
H340.5558490.2219990.7139910.025*
C350.4189(2)0.30857(13)0.7176(2)0.0198(4)
H350.3611680.2796900.7535840.024*
C360.3885(2)0.38644(13)0.6871(2)0.0163(4)
H360.3103020.4096970.7028740.020*

Source of material

All chemicals and solvents were used as purchased without purification. The melting point was determined on a Mel-temp II digital melting point apparatus and was uncorrected. The IR spectrum was obtained on a Bruker Vertex 70v FTIR Spectrometer from 4000 to 400 cm−1.

Triphenyltin iodide was prepared from the reaction of triphenyltin chloride (Merck) with sodium iodide (Sigma-Aldrich) [5]. Triphenyltin iodide (0.48 g, 1 mmol) and triphenylphosphine oxide (Sigma-Aldrich; 0.27 g, 1 mmol) in chloroform (30 mL) were refluxed for 2 h. After filtration, the filtrate was evaporated slowly until yellow crystals were formed. The crystals were filtered, washed with a minimum amount of hexane and air-dried. Yield: 0.21 g (28%). M.pt: 370–372 K. IR (cm−1) 1590 (m) ν(C—C), 1116 (m) ν(P—O), 1070 (m) ν(C—O), 446 (w) ν(Sn—O).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). Owing to poor agreement, one reflection, i.e. (3 3 1), was omitted from the final cycles of refinement. The absolute structure was determined based on differences in the Friedel pairs included in the data set.

Comment

The crystal and molecular structures of the title compound, Ph3SnI⋅O=PPh3, (I), were determined as part of an on-going investigation of oxide adducts of organotin species, such as phosphineoxide [6], arsineoxide [7] and sulphoxide [8], [9]. A search of the crystallographic literature [10] reveals there are no reports of simple R3SnI⋅O=PR’3 adducts.

The molecular structure of (I) is shown in the figure (70% displacement ellipsoids). The tin atom exists within a C3IO donor set defined by the three ipso-carbon atoms of the phenyl substituents [range of Sn—C bond lengths: Sn—C7 = 2.122(2) Å to Sn—C1 2.138(2) Å], an iodide [Sn—I1 = 2.8699(2) Å] and the phosphineoxide-O1 atom [2.3517(15) Å]. The resultant penta-coordinated geometry is based on a trigonal bipyramid with electronegative substituents occupying axial positions; the I1—Sn—O1 axial angle is 178.43(4)°. The tin-bound organo substituents occupy equatorial positions with the range of C—Sn—C angles being 117.73(8)° for C1—Sn—C7, to 119.98(8)° for C1—Sn—C13. The Sn atom lies 0.1910(12) Å out of the C3 equatorial plane in the direction of the I1 atom. The P1—O1 bond length is 1.5044(15) Å and the Sn—O1—P1 angle is 146.39(9)°. When the molecule is viewed down the spine, the configuration of the two sets of phenyl rings is staggered, allowing for the bent Sn—O—P angle.

The molecular packing of (I) is largely devoid of directional interactions. The only notable interaction is an end-on Sn—I⋯π(phenyl) interaction [Sn—I1⋯Cg(C31—C36)i: I1⋯Cg(C31—C36)i = 3.8518(8) Å with angle at I1 = 154.14(2)° for symmetry operation (i) −1 + x, y, −1 + z]. The mode of association leads to the formation of a linear supramolecular chain along [1 0 1].

A further evaluation of the molecular packing was made by calculating the Hirshfeld surfaces and full and delineated two-dimensional fingerprint plots for (I) using Crystal Explorer 17 [11] and literature protocols [12]. The two most dominant surface contacts, comprising over 90% of all contacts, are H⋯H [64.4%] and C⋯H/H⋯C [23.1%]. The contacts involving iodide are I⋯H/H⋯I [6.9%] and I⋯C/C⋯I [2.0%], with the only remaining contacts being of the type C⋯C [0.7%].

The crystal structures of the chloride (II) [13] and bromide (III) [14] analogues of (I) are known. Crystals of the reported (I)–(III) are not isostructural. In (II), C—H⋯π(phenyl) and C—H⋯Cl contacts are noted. However, in (III), no directional interactions are apparent.

Acknowledgements

Sunway University Sdn Bhd is thanked for financial support of this work through Grant no. STR-RCTR-RCCM-001-2019.

References

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Received: 2019-08-05
Accepted: 2019-09-13
Published Online: 2019-10-11
Published in Print: 2019-12-18

©2019 Kong Mun Lo et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  61. Crystal structure of bis{(N-[(5-chloro-2-oxidophenyl)methylidene]-2-hydroxybenzenecarbohydrazonato)-dioxo-molybdenum(VI)}(μ2-4,4′-bipyridine), C38H26Cl2Mo2N6O10
  62. Crystal structure of dichlorido-octamethyl-bis(μ3-oxido)-bis(μ2-2-(phenylamino)ethanolato-κ2O:O)tetratin(IV), C24H44Cl2N2O4Sn4
  63. The crystal structure of 1-(2-(2-(imidazo[1,5-a]pyridine-4-ium)ethoxy)ethyl)-imidazo[1,5-a]pyridine-4-ium bis(hexafluorophosphate) — acetonitrile (1/1), C18H20ON4F12P2
  64. Crystal structure of cyclo[tetra(μ2-cyanido)-tetracyanido-bis(1,4,7,10-tetraazacyclododecane-κ4N,N′,N′′,N′′′)dinickel(II)dipalladium(II)] hexahydrate, C24H52N16Ni2O6Pd2
  65. Crystal structure of (dimethyl sulfoxide)-dioxido-[2-hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato κ3N,O,O′]molybdenum(VI), C19H20MoN2O6S
  66. Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5
  67. Crystal structure of chlorido-diphenyl-(isopropyl(propyl)carbamodithioato-κ2S,S′)tin(IV), C19H24ClNS2Sn
  68. The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O
  69. The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
  70. Crystal structure of di(naphthalen-2-yl)sulfane, C20H14S
  71. Crystal structure of 3-acetyl-6-bromo-4-hydroxy-2H-chromen-2-one, C11H7BrO4
  72. Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4
  73. The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
  74. The crystal structure of 1,2-bis((4-methoxyphenyl)ethynyl)benzene, C24H18O2
  75. Crystal structure of a low-temperature (100 K) polymorph of catena-poly[(μ2-4,4′-bipyridine-κ2N,N′)-bis(O,O′-diethyldithiophosphato-κ1S)zinc(II)], C18H28N2O4P2S4Zn
  76. The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
  77. Crystal structure of 3-iodophthalic acid, C8H5IO4
  78. The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
  79. The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
  80. Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
  81. A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n
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