Home The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
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The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4

  • Kaoxue Li , Ailing Zhang ORCID logo , Shuhua Cao ORCID logo EMAIL logo and Jianmin Wang
Published/Copyright: April 29, 2024

Abstract

C60H92Br8N4O10Sn4, orthorhombic, Pccn (no. 56), a = 16.5363(14) Å, b = 20.3146(17) Å, c = 22.7452(19) Å, V = 7640.8(11) Å3, Z = 4, Rgt (F) = 0.0424, wRref (F 2) = 0.1254, T = 298 K.

CCDC no.: 2327818.

The crystal 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: White cube
Size: 0.25 × 0.18 × 0.15 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 5.53 mm−1
Diffractometer, scan mode: φ and ω
θ max, completeness: 25.0°, >99 %
N(hkl)measured, N(hkl)unique, R int: 36,828, 6746, 0.083
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3989
N(param)refined: 394
Programs: Olex2, 1 SHELX 2 , 3
Table 2:

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

Atom x y z U iso*/U eq
Sn1 0.46034 (4) 0.84185 (2) 0.02228 (2) 0.04818 (18)
Sn2 0.51176 (3) 1.01197 (2) 0.07157 (2) 0.03932 (16)
Br1 0.63571 (7) 0.72268 (5) 0.31879 (5) 0.0926 (4)
Br2 0.48150 (8) 0.96006 (6) 0.37927 (4) 0.0924 (4)
Br3 0.30051 (6) 0.64107 (4) −0.26451 (4) 0.0662 (3)
Br4 0.45831 (8) 0.88435 (5) −0.30130 (4) 0.0823 (3)
N1 0.5958 (5) 0.7675 (3) 0.1942 (3) 0.078 (2)
H1A 0.6436 0.7808 0.1807 0.116*
H1B 0.5609 0.7646 0.1645 0.116*
H1C 0.6011 0.7282 0.2111 0.116*
N2 0.3242 (4) 0.6789 (3) −0.1348 (3) 0.0594 (19)
H2A 0.2722 0.6874 −0.1281 0.089*
H2B 0.3512 0.6797 −0.1010 0.089*
H2C 0.3290 0.6393 −0.1512 0.089*
O1 0.5182 (4) 0.8440 (3) 0.1166 (2) 0.0713 (19)
O2 0.4824 (3) 0.9436 (2) 0.1466 (2) 0.0508 (14)
O3 0.4286 (4) 0.8520 (2) −0.07033 (19) 0.0491 (14)
O4 0.3926 (4) 0.7508 (3) −0.0501 (2) 0.0705 (19)
O5 0.4814 (3) 0.9395 (2) 0.01336 (18) 0.0428 (13)
C1 0.3462 (6) 0.8360 (4) 0.0632 (3) 0.061 (2)
H1D 0.3354 0.7903 0.0726 0.074*
H1E 0.3486 0.8602 0.0999 0.074*
C2 0.2762 (6) 0.8624 (4) 0.0272 (4) 0.072 (3)
H2D 0.2672 0.8332 −0.0059 0.087*
H2E 0.2911 0.9051 0.0116 0.087*
C3 0.1975 (7) 0.8694 (5) 0.0612 (4) 0.079 (3)
H3A 0.1777 0.8258 0.0710 0.095*
H3B 0.2086 0.8922 0.0979 0.095*
C4 0.1315 (7) 0.9064 (6) 0.0285 (4) 0.099 (4)
H4A 0.1500 0.9499 0.0193 0.149*
H4B 0.0841 0.9090 0.0528 0.149*
H4C 0.1187 0.8834 −0.0072 0.149*
C5 0.5654 (7) 0.7853 (4) 0.0050 (4) 0.090 (4)
H5A 0.5756 0.7860 −0.0370 0.108*
H5B 0.6111 0.8061 0.0242 0.108*
C6 0.5608 (8) 0.7140 (5) 0.0251 (5) 0.107 (4)
H6A 0.5168 0.6921 0.0048 0.128*
H6B 0.5492 0.7127 0.0669 0.128*
C7 0.6396 (9) 0.6769 (5) 0.0132 (6) 0.119 (5)
H7A 0.6559 0.6834 −0.0274 0.143*
H7B 0.6822 0.6937 0.0384 0.143*
C8 0.6269 (11) 0.6038 (7) 0.0250 (6) 0.166 (7)
H8A 0.6021 0.5982 0.0628 0.249*
H8B 0.6782 0.5816 0.0245 0.249*
H8C 0.5925 0.5856 −0.0048 0.249*
C9 0.4117 (6) 1.0652 (4) 0.1033 (5) 0.080 (3)
H9A 0.4199 1.0737 0.1449 0.096*
H9B 0.4101 1.1074 0.0834 0.096*
C10 0.3313 (8) 1.0322 (6) 0.0956 (6) 0.118 (4)
H10A 0.3346 0.9888 0.1131 0.141*
H10B 0.3220 1.0263 0.0538 0.141*
C11 0.2581 (8) 1.0671 (6) 0.1214 (6) 0.117 (4)
H11A 0.2696 1.1138 0.1253 0.140*
H11B 0.2123 1.0621 0.0952 0.140*
C12 0.2383 (10) 1.0396 (7) 0.1791 (6) 0.153 (6)
H12A 0.1866 1.0182 0.1772 0.229*
H12B 0.2364 1.0743 0.2077 0.229*
H12C 0.2789 1.0081 0.1902 0.229*
C13 0.6358 (6) 0.9973 (5) 0.0874 (4) 0.075 (3)
H13A 0.6477 0.9519 0.0774 0.090*
H13B 0.6650 1.0245 0.0595 0.090*
C14 0.6718 (7) 1.0098 (6) 0.1467 (5) 0.099 (4)
H14A 0.6364 0.9911 0.1763 0.119*
H14B 0.6737 1.0570 0.1532 0.119*
C15 0.7567 (7) 0.9817 (6) 0.1552 (5) 0.101 (4)
H15A 0.7886 0.9924 0.1207 0.121*
H15B 0.7814 1.0036 0.1885 0.121*
C16 0.7615 (9) 0.9083 (7) 0.1652 (6) 0.131 (5)
H16A 0.7364 0.8975 0.2020 0.197*
H16B 0.8172 0.8949 0.1660 0.197*
H16C 0.7340 0.8858 0.1339 0.197*
C17 0.5083 (5) 0.8859 (4) 0.1569 (3) 0.047 (2)
C18 0.5279 (5) 0.8697 (3) 0.2191 (3) 0.0428 (19)
C19 0.5679 (5) 0.8115 (4) 0.2343 (3) 0.050 (2)
C20 0.5811 (5) 0.7994 (4) 0.2944 (4) 0.057 (2)
C21 0.5541 (6) 0.8430 (5) 0.3368 (4) 0.066 (3)
H21 0.5619 0.8337 0.3765 0.079*
C22 0.5158 (6) 0.8999 (4) 0.3203 (3) 0.059 (2)
C23 0.5031 (5) 0.9130 (4) 0.2622 (3) 0.047 (2)
H23 0.4773 0.9518 0.2514 0.057*
C24 0.4038 (5) 0.7944 (4) −0.0867 (3) 0.047 (2)
C25 0.3927 (5) 0.7826 (3) −0.1503 (3) 0.0414 (18)
C26 0.3553 (5) 0.7258 (3) −0.1722 (3) 0.0425 (18)
C27 0.3507 (5) 0.7179 (3) −0.2332 (3) 0.046 (2)
C28 0.3813 (5) 0.7631 (4) −0.2712 (3) 0.053 (2)
H28 0.3780 0.7560 −0.3115 0.064*
C29 0.4172 (5) 0.8192 (4) −0.2499 (3) 0.052 (2)
C30 0.4225 (5) 0.8288 (3) −0.1900 (3) 0.0449 (19)
H30 0.4467 0.8670 −0.1758 0.054*

1 Source of materials

In a representative experiment 2-amino-3,5-dibromobenzoic acid (0.295 g; 1 mmol) was dissolved in toluene in 15 mL. To this solution 0.068 g (1.0 mmol) sodium ethoxide was added. After stirring the mixture for 30 min, dibutyltin oxide (0.249 g, 1 mmol) was added. The reaction mixture was heated to 100 °C and stirred continuously for 6 h at this temperature. After the reaction mixture was filtered, the solvent was evaporated in vacuo, cube shaped crystals were obtained from acetonitrile solution.

2 Experimental details

Using Olex2, 1 the structure was solved with the ShelXS-1997 2 structure solution program using Direct Methods and refined with the ShelXL-1997 3 refinement package. Coordinates of hydrogen atoms were refined with constraints. Their U iso values were set to 1.2U eq of the parent atoms for methylene group and aromatic ring, U iso(H) = 1.5 times U eq(methyl group).

3 Comment

Since cisplatin has been used as an antitumor drug, the antitumor activity of metal complexes has received increasing attention. 4 , 5 In addition to antitumor activity, organotin complexes have attracted more attention because they have antibacterial, antifungal and insecticidal properties. 6 8 In addition, many crystal structures of organic tin compounds have been reported. 9 , 10

The molecular structure of title complex is shown in the figure (70 % displacement ellipsoids). It has a tetranuclear structure, which contains four 2-amino-3,5-dibromobenzoate anions, eight n-butyl anions, two oxygen dianions and four tin cations. In the complex, each tin ion is five-coordinated in a trigonal bipyramid with the n-butyl substituents occupying axial positions. In the asymmetric unit, one tin atoms coordinating with two oxygen atoms from the carboxyl group, one oxygen dianionic group, and two n-butyl groups, the other tin atoms coordinating with one carboxyl oxygen atom, two oxygen dianionic groups, and two n-butyl groups. Four tin ions in the unit form a parallelogram on the same plane, with adjacent edges of 3.686 Å and 3.731 Å, respectively. The bond lengths of Sn–O range from 2.024(4) Å to 2.348(5) Å [Sn1–O1 = 2.348(5) Å, Sn1–O3 = 2.181(4) Å, Sn1–O5 = 2.024(4) Å, Sn2–O5 = 2.043(4) Å, Sn2–O51 = 2.172(4) Å, Sn2–O2 = 2.252(4) Å], which are not significantly different from the bond lengths of other organic tin Sn–O bonds [2.2270(12) Å]. 11 The bond lengths of Sn–C range from 2.103(10) Å to 2.119(11) Å, [Sn1–C1 = 2.107(9) Å, Sn1–C5 = 2.119(11) Å, Sn2–C9 = 2.119(11) Å, Sn2–C13 = 2.103(10) Å], which are in the expected ranges. The bond angles of C–Sn–O range from 81.1(3)° to 141.8(4)°. The bond angles of O–Sn–O range from 76.31(19)° to 168.1(2)° 12 .

There are intramolecular hydrogen bonds, which are N1–H…O1 [distance = 2.679 Å] and N2–H…O4 [distance = 2.669 Å]. There is no hydrogen bonding between molecules. The entire molecule is arranged in a p–p stacking manner to form a network structure. The centroid–centroid distance is 3.674 Å and the shift distance is 1.090 Å.


Corresponding author: Shuhua Cao, College of Chemistry, Chemical and Environmental Engineering, Weifang University, Weifang, Shandong, P.R. China, E-mail:

Acknowledgements

We gratefully acknowledge support by Shandong Province Higher Education Undergraduate Teaching Reform Research Project (M2023099) for financial support.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Shandong Province Higher Education Undergraduate Teaching Reform Research Project (M2023099).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2024-02-29
Accepted: 2024-04-16
Published Online: 2024-04-29
Published in Print: 2024-08-27

© 2024 the author(s), published by De Gruyter, Berlin/Boston

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

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  49. Crystal structure of 5,6,3′,4′,5′-pentamethoxy-flavone dihydrate, C20H24O9
  50. Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
  51. Crystal structure of methyl (3R)-1-(2-bromo-4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride hydrate, C19H19BrClFN2O3
  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
  53. The crystal structure of 1-cyclohexyl-3-(p-tolyl)urea, C14H20N2O
  54. Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P
  55. The crystal structure of ethyl 3-(1-methyl-1H-indole-2-carbonyl)-2-phenylquinoline-4-carboxylate, C28H22N2O3
  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 )
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N -dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
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