Home Physical Sciences The crystal structure of 1,1,1,3,3,3-hexaphenyldistannoxane – 2,2′-bipyridine (1/1), C46H38N2OSn2
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The crystal structure of 1,1,1,3,3,3-hexaphenyldistannoxane – 2,2′-bipyridine (1/1), C46H38N2OSn2

  • Junshan Sun EMAIL logo and Yan Kong
Published/Copyright: February 4, 2019

Abstract

C46H38N2OSn2, triclinic, P1̄ (no. 2), a = 9.657(4) Å, b = 9.679(4) Å, c = 24.324(9) Å, α = 95.397(5)°, β = 90.138(5)°, γ = 119.283(5)°, V = 1971.2(12) Å3, Z = 2, Rgt(F) = 0.0369, wRref(F2) = 0.0873, T = 298(2) K.

CCDC no.: 1887913

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colorless block
Size:0.33 × 0.29 × 0.27 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.30 mm−1
Diffractometer, scan mode:Bruker SMART APEX II CCD,
θmax, completeness:25.0°, 99%
N(hkl)measured, N(hkl)unique, Rint:10366, 6869, 0.030
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4869
N(param)refined:460
Programs:Bruker [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
Sn10.80203(4)0.47262(3)0.17784(2)0.04559(11)
Sn20.89118(4)0.58633(3)0.32355(2)0.04600(11)
N1−0.1008(5)0.7895(5)0.50785(17)0.0689(12)
N20.6154(5)0.3999(5)0.99172(18)0.0688(12)
O10.8850(4)0.4722(4)0.25156(12)0.0583(8)
C10.7707(5)0.2525(5)0.13838(18)0.0450(11)
C20.8460(6)0.1797(5)0.1615(2)0.0594(13)
H20.9080740.2268790.1943040.071*
C30.8304(7)0.0375(6)0.1365(2)0.0721(16)
H30.882248−0.0095090.1525700.087*
C40.7395(7)−0.0336(6)0.0886(2)0.0760(16)
H40.729023−0.1289920.0720010.091*
C50.6639(7)0.0356(6)0.0652(2)0.0760(17)
H50.601326−0.0132840.0326310.091*
C60.6794(6)0.1782(6)0.0895(2)0.0614(14)
H60.6280910.2247080.0727670.074*
C70.9855(5)0.6811(5)0.1471(2)0.0502(12)
C81.1274(6)0.7718(6)0.1766(2)0.0712(15)
H81.1421220.7431470.2107050.085*
C91.2495(7)0.9051(7)0.1572(3)0.099(2)
H91.3457370.9642720.1777310.119*
C101.2279(8)0.9497(7)0.1074(3)0.096(2)
H101.3090541.0402070.0942980.115*
C111.0883(8)0.8619(7)0.0772(2)0.0799(17)
H111.0736940.8922700.0435080.096*
C120.9684(6)0.7283(6)0.0964(2)0.0623(13)
H120.8737360.6680500.0750640.075*
C130.5864(5)0.4788(5)0.18301(18)0.0488(11)
C140.5735(6)0.6072(6)0.1678(2)0.0662(14)
H140.6614900.6919610.1547410.079*
C150.4337(8)0.6117(7)0.1717(3)0.0829(18)
H150.4283020.6990570.1612580.100*
C160.3040(8)0.4900(9)0.1905(2)0.0827(18)
H160.2102700.4945930.1933700.099*
C170.3097(7)0.3601(8)0.2054(2)0.0880(19)
H170.2199770.2758380.2179220.106*
C180.4518(6)0.3550(6)0.2018(2)0.0672(14)
H180.4557920.2668560.2121190.081*
C190.8896(6)0.8033(5)0.31503(18)0.0494(11)
C201.0294(7)0.9475(6)0.3240(2)0.0724(15)
H201.1235700.9490600.3334200.087*
C211.0307(8)1.0894(6)0.3190(3)0.0844(18)
H211.1245161.1858070.3264100.101*
C220.8952(8)1.0876(7)0.3032(2)0.0797(17)
H220.8969941.1827550.2986830.096*
C230.7574(8)0.9484(7)0.2941(2)0.0840(18)
H230.6647220.9483690.2836600.101*
C240.7534(6)0.8050(6)0.3003(2)0.0663(14)
H240.6577020.7098200.2943610.080*
C250.6856(5)0.4172(5)0.36092(18)0.0430(10)
C260.6049(6)0.2606(6)0.3373(2)0.0596(13)
H260.6390860.2316320.3047730.071*
C270.4745(6)0.1467(6)0.3611(3)0.0740(16)
H270.4231770.0416360.3449710.089*
C280.4205(6)0.1877(7)0.4084(3)0.0760(16)
H280.3316480.1114780.4242130.091*
C290.4989(7)0.3419(7)0.4320(2)0.0755(16)
H290.4630670.3708180.4641560.091*
C300.6313(6)0.4561(6)0.4084(2)0.0629(14)
H300.6838250.5604660.4252420.075*
C311.1138(5)0.6321(5)0.35928(18)0.0465(11)
C321.1920(6)0.5598(6)0.3327(2)0.0652(14)
H321.1469070.4940900.2997890.078*
C331.3337(7)0.5829(7)0.3536(3)0.0838(18)
H331.3843400.5331170.3350730.101*
C341.4016(6)0.6796(7)0.4021(3)0.0793(17)
H341.4978760.6948870.4166220.095*
C351.3280(6)0.7523(6)0.4286(2)0.0726(16)
H351.3752050.8192960.4610430.087*
C361.1835(6)0.7285(5)0.4081(2)0.0570(13)
H361.1330530.7774860.4272410.068*
C370.8145(8)0.6751(8)0.9459(2)0.0862(19)
H370.8817130.7684060.9307310.103*
C380.6741(6)0.6526(6)0.9661(2)0.0630(14)
H380.6446670.7303940.9643170.076*
C390.5759(5)0.5146(6)0.98902(18)0.0500(12)
C400.8552(8)0.5590(9)0.9484(2)0.092(2)
H400.9501000.5713900.9348230.110*
C410.7534(8)0.4252(8)0.9710(3)0.0854(18)
H410.7811520.3460750.9723300.103*
C420.1908(8)0.8771(9)0.5585(2)0.0840(18)
H420.2890690.9071040.5756820.101*
C430.1631(6)0.9876(7)0.5369(2)0.0667(14)
H430.2432211.0934360.5389670.080*
C440.0179(5)0.9424(5)0.51227(17)0.0487(11)
C450.0727(9)0.7232(8)0.5544(2)0.0873(19)
H450.0884820.6456720.5685240.105*
C46−0.0678(8)0.6853(7)0.5296(3)0.0856(18)
H46−0.1479230.5794050.5272680.103*

Source of material

In a typical experiment, 2,3,4,5-tetrafluorobenzoic acid (0.194 g; 1 mmol), triphenyltin chloride (0.385 g, 1 mmol) and sodium ethoxide (0.748 g, 1.1 mmol), in the presence of 2,2′-bipy (0.156 g, 1 mmol) were dissolved in benzene. This mixture was heated to 40 °C for 3 h, resulting in a colorless solution. Crystals of the title compound were obtained by slow evaporation within one week.

Experimental details

All hydrogen atom positions were taken from a difference Fourier map. Hydrogen atoms were assigned with common isotropic displacement factors Uiso(H) = 1.2 times Ueq. All the H atoms were refined as riding on their parent atom.

Comment

Organotin compounds form an important class of compounds and have received much interest in recent years, not only due to their intrinsic interest but owing to their varied applications. Some are used as catalysts and stabilizers, and certain derivatives are biocides, act as antifouling agents and wood preservatives [3]. In order to explore the impact of organotin compound they have been studied intensively [4], [5], [6], [7]. Interestingly, Gielen et al. reported that fluorinated organotin carboxylates own anticances activity [8], [9] .

So our interest in the structures of organotin(IV) complexes containing N and O atoms has prompted us to embark the 2,3,4,5-tetrafluorobenzoate ligand and 2,2′-bipy. Unfortunately, the carboxylate did not coordinate to tin. Two triphenyltin link one oxygen atom, which is similiar to reported structures [10], [11], [12], [13]. The crytal structure of the title complex is shown in the figure. The title complex shows additionally two 2,2′-bipy molecules both located around inversion centers. The distance of O—Sn are 1.964(3) Å and 1.967(4) Å, which are much smaller than the reported in literature [14], [15]. The angle of Sn—O—Sn is 131.46(19)°. Interestingly, the angles of O—Sn—C and C—Sn—C are from 100° to 113°, which are closer to the regular tetrahedral configuration. Finally it should be mentioned that solvent-free parent structure is known for decades [16].

Acknowledgements

Financial support from the Shandong Provincial Higher Education Research and Development Program Project (No. J18KB049) and Talent Foundation of Taishan University (No. Y2015-1-002) are gratefully acknowledged.

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Received: 2018-10-28
Accepted: 2018-12-29
Published Online: 2019-02-04
Published in Print: 2019-03-26

©2019 Junshan Sun 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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  51. Crystal structure of (E)-2-((4-chlorophenyl)(phenyl)methylene)hydrazine-1-carbothioamide, C14H12ClN3S
  52. Crystal structure of 1-benzyl-3-cyano-6-phenyl-1,2-dihydropyridine, C19H16N2
  53. Isolation and crystal structure of 4-((2-(methoxycarbonyl)phenyl)amino)-2-methyl-4-oxobutanoic acid from Delphinium Grandiflorum, C13H15N1O5
  54. Crystal structure of tetraqua-bis(4-(hydroxymethyl)benzoato-κO)nickel(II), C16H22O10Ni
  55. Crystal structure of ajacisine D monohydrate, C30H44N2O9
  56. The crystal structure of (E)-4-(1-(2-aminophenylimino)ethyl)benzene-1,3-diol, C14H14N2O2
  57. Crystal structure of poly[(μ4-(4H-1,2,4-triazol-4-yl)phenyl)acetato-κ4N,N′,O,O′)(formiato-κ1O)cobalt(II)], C11H9CoN3O4
  58. The crystal structure of bis tetrabutylammonium bis(μ3-2,2,2-tri(hydroxymethyl)ethyl-4-((3-methoxy-3-oxopropyl)amino)-4-oxobutanoato)-(μ6-oxido)-hexakis(μ2-oxido)-hexaoxido-hexavanadium(V), C58H112N4O29V6
  59. Crystal structure of (N-benzylpropane-1,3-diamine-κ2N, N′)(2,2′-bipyridine-κ2N,N′)platinum(II) chloride, C20H24Cl2N4Pt
  60. Crystal structure of 5-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-N-phenyl-2-amine, C23H16ClN5O
  61. Crystal structure of poly-[(μ2(carboxylatomethyl)((3-nitrophenyl)sulfonyl)amido-κ3N: O:O′)(μ2-4,4′-bipyridine-κ2N:N′)copper(II)], C18H14CuN4O6S
  62. Crystal structure of poly-[(μ2-(carboxylatomethyl)((3-nitrophenyl)sulfonyl)amido-κ3N:O:O′)(μ2-4,4′-bipyridine-κ2N:N′) nickel(II)], C18H14NiN4O6S
  63. Crystal structure of N-((3R,10S,13S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-N-methylbenzamide, C31H48N2O
  64. The crystal structure of dichloroido(1,3-bis(2,6-dimethyl-phenyl)-1H-3l4-imidazol-2-yl)(2-methyl-4,5-dihydrooxazol-κN)palladium(IV)-water (1/1), C23H29Cl2N3O2Pd
  65. Crystal structure of catena-poly[dibromido-{μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O}zinc(II)], C34H32Br4N8O2Zn2
  66. Crystal structure of diaqua-dichlorido-bis(μ2-2-(((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)dicobalt(II), C36H36Cl2N6O6Co2
  67. Crystal structure of catena-poly[diaqua-(μ2-1,2-bis(4-pyridinyl)ethyane-κ2N:N′)-(μ2–pyridazine-4,5-dicarboxylato-κ2O:O′)]dizinc(II) dihydrate, C12H12ZnN3O6
  68. The crystal structure of 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro)diazene oxide, C12H6Cl2N4O5
  69. Crystal structure of 2-isopropylthioxanthone, C16H14OS
  70. Crystal structure of methyl 2-(4-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C19H17N5O2
  71. Crystal structure of 4,4-dimethyl-2-(trifluoromethyl)-4,5-dihydro-1H-imidazole, C6H9F3N2
  72. Crystal structure of N-methylanilinium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate monohydrate, C22H21NO8S
  73. Crystal structure of methyl 4-acetoxybenzoate, C10H10O4
  74. Crystal structure of catena-poly[(bis(μ-1,1′-[(5-methoxy-2,4,6-trimethyl-1,3-phenylene)bis(methylene)]bis(1H-1,2,4-triazole)-κ2N:N′)-bis(isothiocyanato-κN)manganese(II)], C34H40MnN14O2S2
  75. Crystal structure of N-(2-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
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