Home Crystal structure of catena-poly[(μ2-acetamido-benzoato-κ2O:O′)triphenyltin(IV)], C27H23NO3Sn
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Crystal structure of catena-poly[(μ2-acetamido-benzoato-κ2O:O′)triphenyltin(IV)], C27H23NO3Sn

  • Qi-Bao Wang EMAIL logo , Rui-Fang Ding , Shan-Shan Sun and Lin Ding
Published/Copyright: February 3, 2016

Abstract

C27H23NO3Sn, orthorhombic, P212121, a = 8.9287(7) Å, b = 15.0252(12) Å, c = 18.4531(14) Å, V = 2475.6(3) Å3, Z = 4, Rgt(F) = 0.0315, wRref(F2) = 0.0861, T = 296(2) K.

CCDC no.:: 1446649

The crystal structure is shown in the figure, Tables 13 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Colorless, block, size 0.17×0.24×0.30 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:10.59 cm−1
Diffractometer, scan mode:CCD area detector, φ and ω scans
2θmax:50°
N(hkl)measured, N(hkl)unique:12552, 4356
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4165
N(param)refined:260
Programs:SHELX [5]
Table 2

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

AtomSitexyzUiso
H(3)4a0.088(4)−0.240(3)0.055(2)0.03(1)
H(4)4a−0.063(6)−0.306(4)−0.043(3)0.07(2)
H(7)4a0.087(5)0.003(3)−0.041(3)0.05(1)
H(6)4a−0.044(6)−0.047(4)−0.146(3)0.06(1)
H(9A)4a−0.1570−0.3101−0.29770.167
H(9B)4a−0.1979−0.2200−0.33560.167
H(9C)4a−0.2979−0.2561−0.27230.167
H(11)4a0.27520.15060.30980.142
H(12)4a0.10160.14660.40380.155
H(13)4a−0.11720.07620.38740.171
H(14)4a−0.15270.00040.28660.379
H(15)4a0.0230−0.00790.19790.293
H(17)4a0.47780.15830.02110.291
H(18)4a0.49450.2910−0.03520.389
H(19)4a0.34810.4033−0.00620.273
H(20)4a0.19230.38710.08930.314
H(21)4a0.21020.26260.15700.279
H(23)4a0.56850.01450.04600.103
H(25)4a0.7763−0.07730.03740.131
H(26)4a0.7173−0.15580.23900.150
H(27)4a0.5041−0.06590.24920.118
H(1)4a−0.194(6)−0.259(4)−0.155(3)0.06(1)
H(0AA)4a0.8499−0.16130.13470.137
Table 3

Atomic displacement parameters (Å2).

AtomSitexyzU11U22U33U12U13U23
Sn(1)4a0.32915(3)0.07201(2)0.15567(2)0.0543(2)0.0456(2)0.0488(1)0.0020(1)−0.0015(1)−0.0047(1)
N(1)4a−0.1276(5)−0.2214(3)−0.1666(2)0.073(2)0.052(2)0.051(2)−0.024(2)−0.002(2)0.004(2)
O(1)4a0.2013(4)0.0110(2)0.0739(2)0.076(2)0.042(2)0.065(2)0.000(2)−0.019(2)−0.010(1)
O(2)4a0.2092(4)−0.1205(2)0.1284(2)0.063(2)0.055(2)0.054(2)0.010(1)−0.009(1)−0.002(1)
O(3)4a−0.0070(6)−0.1500(3)−0.2556(2)0.107(3)0.071(2)0.051(2)−0.023(2)0.006(2)0.009(2)
C(1)4a0.1765(5)−0.0741(3)0.0769(2)0.046(2)0.044(2)0.054(2)0.009(2)−0.005(2)−0.005(2)
C(2)4a0.0990(5)−0.1125(3)0.0115(2)0.052(2)0.039(2)0.046(2)0.004(2)0.002(2)−0.003(2)
C(3)4a0.0619(5)−0.2017(3)0.0098(2)0.061(3)0.042(2)0.050(2)−0.001(2)−0.005(2)0.005(2)
C(4)4a−0.0132(6)−0.2370(3)−0.0502(3)0.061(3)0.038(2)0.061(2)−0.011(2)−0.002(2)0.004(2)
C(7)4a0.0583(6)−0.0578(3)−0.0461(3)0.079(3)0.038(2)0.056(2)−0.004(2)−0.008(2)0.002(2)
C(6)4a−0.0194(7)−0.0928(3)−0.1053(3)0.093(4)0.042(2)0.051(2)−0.010(2)−0.012(2)0.007(2)
C(5)4a−0.0506(5)−0.1836(3)−0.1076(2)0.062(3)0.044(2)0.042(2)−0.007(2)0.001(2)0.001(2)
C(8)4a−0.1024(7)−0.2022(4)−0.2366(2)0.078(3)0.064(3)0.047(2)−0.010(3)−0.005(2)0.007(2)
C(9)4a−0.197(1)−0.2515(6)−0.2904(4)0.143(8)0.129(7)0.063(3)−0.060(6)−0.015(4)−0.003(4)
C(10)4a0.1710(6)0.0708(4)0.2421(3)0.057(2)0.074(3)0.070(3)−0.010(3)0.014(2)−0.022(3)
C(11)4a0.1886(8)0.1169(7)0.3040(4)0.065(4)0.188(9)0.101(5)−0.008(5)0.009(4)−0.063(6)
C(12)4a0.082(1)0.1168(8)0.3607(5)0.085(5)0.21(1)0.095(5)0.010(6)0.021(4)−0.053(6)
C(13)4a−0.043(1)0.0747(8)0.3519(6)0.123(7)0.151(9)0.154(8)−0.019(6)0.080(7)−0.049(8)
C(14)4a−0.063(2)0.031(1)0.293(1)0.28(2)0.31(2)0.37(2)−0.21(2)0.25(2)−0.25(2)
C(15)4a0.043(2)0.027(1)0.2385(8)0.21(1)0.30(2)0.22(1)−0.17(1)0.15(1)−0.20(1)
C(16)4a0.3362(8)0.1936(4)0.0963(3)0.085(4)0.053(3)0.091(4)−0.003(3)−0.032(4)0.005(2)
C(17)4a0.421(2)0.206(1)0.038(1)0.24(2)0.17(1)0.32(2)0.08(1)0.14(2)0.17(1)
C(18)4a0.427(2)0.285(1)0.003(2)0.22(2)0.23(2)0.53(4)0.07(2)0.12(2)0.28(3)
C(19)4a0.345(2)0.351(1)0.020(1)0.23(2)0.12(1)0.33(3)−0.09(1)−0.16(2)0.14(1)
C(20)4a0.258(3)0.3417(9)0.076(1)0.47(4)0.069(7)0.24(2)0.07(1)−0.14(2)0.007(9)
C(21)4a0.264(3)0.2645(7)0.1138(7)0.47(3)0.093(7)0.130(8)0.13(1)−0.05(1)−0.018(6)
C(22)4a0.5191(5)−0.0128(3)0.1491(3)0.052(2)0.051(2)0.063(3)0.001(2)−0.001(2)−0.003(2)
C(23)4a0.5981(8)−0.0189(5)0.0859(4)0.084(4)0.073(4)0.100(5)0.012(3)0.035(4)0.015(3)
C(25)4a0.7228(9)−0.0746(6)0.0805(5)0.091(4)0.087(5)0.150(7)0.018(4)0.054(5)0.012(5)
C(26)4a0.687(1)−0.1212(7)0.1998(5)0.139(8)0.130(7)0.105(6)0.070(7)−0.022(6)0.006(5)
C(27)4a0.5598(9)−0.0662(6)0.2066(4)0.123(6)0.097(5)0.074(4)0.045(5)−0.018(4)0.004(4)
C(0AA)4a0.7661(9)−0.1248(6)0.1381(6)0.070(4)0.100(6)0.17(1)0.034(4)−0.005(5)0.003(6)

Source of material

Method 1: To a solution of 4-acetylanthranilic acid (0.179 g, 1.0 mmol) in 30 mL acetonitrile was added triphenyltin chloride (0.385 g, 1.0 mmol) and 5 drops of triethylamine. The mixture was reflux with stir for 5 h, then the solvent was removed under reduced pressure. The residue was recrystallized from dichloromethane/n-hexane to give colorless crystals 0.474 g, yield 89.9%. Method 2: To a solution of (4-aminobenzoato)-triphenyl-tin(IV) [1] (0.486 g, 1.0 mmol) in 30 mL acetonitrile was added acetic anhydride (0.153 g, 1.5 mmol). The mixture was reflux with stir for 1.5 hours, then the solvent was removed under reduced pressure. The residue was recrystallized from dichloromethane/n-hexane to give colorless crystals 0.503 g, yield 95.4%.

Experimental details

All the H atoms were positioned geometrically and refined using a riding model, except of the nitrogen bonded hydrogen atom, which was refined freely. The Uiso values of the hydrogen atoms of methyl groups were set to 1.5 Ueq(C) and the Uiso values of all other hydrogen atoms were set to 1.2 Ueq(C, N). An unresolved disorder of the phenyl groups is present in the title structure.

Discussion

Organotin(IV) compounds with carboxyl groups have been extensively studied owing to their antitumor activities as well as their diversities in structure [2, 3]. In general, the biological activity of organotin compounds is strongly influenced by the structure of the molecule and the coordination number of the tin atom(s). When additional donor atoms (e.g. N, O or S) are introduced in the molecule, the structure of the compounds may change [4]. In this study, when acetyl group was introduced in (4-aminobenzoato)triphenyl-tin(IV), the coordination of the tin atom changed from tetrahedral to trigonal bipyramidal [1].

In the crystal structure of the title compound, the tin atom is fivefold coordinated in a trigonal bipyramidal geometry, with three carbon atoms from the phenyl rings occupying the equatorial position, one oxygen atom from the carboxyl group and the oxygen atom from the acetyl group of the other 4-aminobenzoato ligand occupying the axial position. Thus, the resulting structure is a one-dimensional chain structure. The distance of Sn1-O3A (2.564 Å) is longer than that of the Sn1-O1 (2.099 Å). The Sn1, C10, C16 and C20 atoms are almost coplanar with the mean deviation 0.0124°.


Corresponding author: Qi-Bao Wang, Department of Pharmacy, Jining Medical College, Xueyuan Road 669, Rizhao, P. R. China, e-mail:

Acknowledgements:

This work was supported by the Foundation of Shandong Educational Committee No. J15LC23, NSFS ZR2015BL005 and Foundation for the Youth of JNMC No. Jyq2011km030 and the Project of Science and Technology of JNMC No. JY2013 K.006.

References

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Received: 2015-8-5
Accepted: 2016-1-11
Published Online: 2016-2-3
Published in Print: 2016-3-1

©2016 Qi-Bao Wang et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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  60. Crystal structure of (2,5-dihydroxyphenyl)-(4-hydroxy-3,5-dimethoxyphenyl)methanone, C15H14O6
  61. Crystal structure of dichlorido[bis(2-hydroxyethyl)5′-([2,2′:6′,2′′-terpyridin]-4′-yl)-[1,1′:3′,1′′-terphenyl]-4,4′′-dicarboxylato]zinc(II), C39H31Cl2N3O6Zn
  62. Crystal structure of bis[4-(3-carboxy-6-fluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium] benzene-1,4-dicarboxylate (C20H18F2N3O3)2(C8H4O4), C48H40F4N6O10
  63. Crystal structure of (2,5-dihydroxyphenyl)-(4-methoxyphenyl)methanone, C14H12O4
  64. Crystal structure of photochromic 1-(2-methyl-5-phenyl-3-thienyl-2-[2-methyl-5-(4-ethoxylphenyl)-3-thienyl] 3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H22F6OS2
  65. Crystal structure of poly[diaquabis(μ2-biphenyl-2,4′-dicarboxylato-κ2O:O′)tris(μ2-1,1′-biphenyl-4,4′-diylbis(1H-imidazole)-κ2N:N′)dicobalt(II)] monohydrat, C82H64N12O11Co2
  66. Crystal structure of 2-amino-4-(3,4-difluorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H12N2O2F2
  67. Crystal structure of poly[(di-μ2-aqua-κ2O:O)bis(μ5-oxalato-1:2κ2O1; 1κ1O2; 3:4:5κ3O3; 3κ1O4)(μ4-oxalato-1:2κ2O1; 2:3κ2O2; 3:4κ2O3; 4:1κ2O4)dizinc(II)disodium(I)]
  68. Crystal structure of tetraethylammonium hexachloridotantalate(V), C8H20Cl6NTa
  69. Crystal structure of (E)-2,4-dibromo-6-(((2-nitrophenyl)imino)methyl)phenol, C13H8Br2N2O3
  70. The crystal structure of 6-chloro-2,4-diphenylquinoline
  71. Crystal structure of (E)-2-(((1,10-phenanthrolin-5-yl)imino)methyl)-5-methylphenol monohydrate, C20H15N3O·H2O
  72. Crystal structure of tris(3-(2-pyridyl)pyrazole)zinc(II)tetrachlorido zincate(II), C24H21Cl4N9Zn2
  73. Crystal structure of 4-chloro-N,N-diethyl-6-(piperidin-1-yl)-1,3,5-triazin-2-amine, C12H20ClN5
  74. The crystal structure of 4-allyl-5-benzyl-2,4-dihydro-3H-1,2,4-triazol-3-one, C12H13N3O
  75. Crystal structure of diethyl 2-(((2-(pyridin-3-ylthio)phenyl)amino)methylene)malonate, C19H20N2O4S
  76. Crystal structure of fac-tricarbonyl(2-(isopropylimino)methyl-5-methylphenolatido-κ2N,O)(pyridine-κN)rhenium(I), C19H19N2O4Re
  77. Crystal structure of 1,3,6,8-tetrakis(p-tolylthio)pyrene, C44H34S4
  78. Crystal structure of catena-poly-(diaqua-(μ2-1,2-bis(4-pyridyl)ethene-κ2N:N′)-(4-methylphthalato-κ2O,O′)-cobalt(II)trihydrate, C21H26CoN2O9
  79. Crystal structure of tetraethylammonium fac-tricarbonyl(hexafluoroacetylacetonato-κ2O,O′)-(nitrato-κO)rhenium(I), C16H21O8N2F6Re
  80. Crystal structure of 3-(thiophen-2-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carboxamide
  81. Crystal structure of bis(1-ethyl-3-methylimidazolium) tetrabromidocadmate(II), [C6H11N2]2[CdBr4]
  82. Crystal structure of N′-(adamantan-2-ylidene)-isonicotinohydrazide, C16H19N3O
  83. Crystal structure of trans-tetraaquabis(4-(pyridin-4-ylsulfonyl)pyridine-κN)cobalt(II) diperchlorate dihydrate, C20H28Cl2CoN4O18S2
  84. Crystal structure of (Z)-4-(furan-2-yl(p-tolylamino)methylene)-3-methyl-1-p-tolyl-1H-pyrazol-5(4H)-one, C23H21N3O2
  85. Crystal structure of 2-[(4-fluorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile, C16H16FN3OS
  86. Crystal structure of poly[octaaqua-tris(benzene-1,2,4,5-tetracarboxylato)tetralanthanum(III)] hexahydrate, C30H34La4O38
  87. Crystal structure of trans-tetraaqua-bis(4,4′-sulfonyldipyridine-κN)zinc(II) diperchlorate dihydrate, C20H28Cl2ZnN4O18S2
  88. Crystal structure of 4-nitro-thiophene-2-carboxylic acid, a structure with a Z′ = 4, C5H3NO4S
  89. Crystal structure of dirubidium trimercury(II) tetraselenide, Rb2Hg3Se4
  90. Crystal structure of 5-(adamantan-1-yl)-3-[(4-chloroanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, C19H22ClN3OS
  91. Crystal structure of hexaaquamagnesium(II) 5,5′-bitetrazole-1,1′-diolate, C2H12N8O8Mg
  92. The crystal structure of catena-poly[(μ2-1,1′-benzene-1,4-diylbis(1H-benzimidazole-κ2N:N′)silver(I)] nitrate, C20H14N5AgO3
  93. The crystal structure of 1-(2-(4-chlorophenoxy)-4-chlorophenyl)ethanone, C14H10Cl2O2
  94. The crystal structure of 3,5-dinitro-1,3,5-oxadiazinane, C3H6N4O5
  95. Crystal structure of methyl 5-methoxy 1H-indole-2-carboxylate, C11H11NO3
  96. Crystal structure of (Z)-1-(((3-acetyl-2-hydroxyphenyl)amino)methylene)naphthalen-2(1H)-one, C19H15NO3
  97. Crystal structure of (Z)-5-(4-chlorobenzylidene)-2-thioxothiazolidin-4-one —dimethylsulfoxide (1:1), C12H12ClNO2S3
  98. Crystal structure of 5,5′-((4-(trifluoromethyl)phenyl)methylene)bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione) – diethylamine – dichloromethane (1/1/1) C25H32Cl2F3N5O6
  99. Crystal structure of 2-(dimethylsulfanylidene)-N-(4-methoxyphenyl)-3-oxo-3-phenylpropanamide
  100. Crystal structure of (1,10-phenanthroline-κ2N,N′)bis(thiocyanato-κN)platinum(II), C14H8N4PtS2
  101. Crystal structure of di(μ2-chlorido)bis[2-(2-pyridyl)phenyl-κ2N,C1]dipalladium(II), C22H16Cl2N2Pd2
  102. Crystal structure of trans-dibromidodi(pyridine-κN)palladium(II), PdBr2(C5H5N)2
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