Home Physical Sciences Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn
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Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn

  • Sheng-Cai Xue and Shuang Lü ORCID logo EMAIL logo
Published/Copyright: August 7, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 5

Abstract

C33H22O6Sn, triclinic, P1̄ (no. 2), a = 9.5394(11) Å, b = 10.2394(12) Å, c = 15.3202(18) Å, α = 105.195(3)°, β = 91.321(2)°, γ = 105.703(3)°, V = 1383.1(3) Å3, Z = 2, Rgt(F) = 0.0452, wRref(F2) = 0.1115, T = 298(2) K.

CCDC no.: 2365690

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: Orange block
Size: 0.28 × 0.16 × 0.11 mm
Wavelength:

μ:		 Mo Kα radiation (0.71073 Å)

0.97 mm−1
Diffractometer, scan mode:

θmax, completeness:		 Bruker SMART-1000, φ and ω

25.0°, 98 %
N(hkl)measured, N(hkl)unique, Rint: 6729, 4782, 0.038
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs),
N(param)refined: 363
Programs: Bruker, 1 SHELX, 2 , 3 Olex2 4
Table 2:

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

Atom x y z Uiso*/Ueq
Sn1 0.29797 (4) 0.27801 (3) 0.35704 (2) 0.05113 (14)
O1 −0.2602 (4) −0.0751 (3) −0.0159 (3) 0.0672 (10)
H1 −0.320996 −0.140775 −0.051958 0.101*
O2 −0.3973 (4) −0.3386 (3) −0.0980 (2) 0.0600 (9)
O3 −0.5583 (4) −0.5997 (4) −0.1698 (2) 0.0637 (9)
H3 −0.536892 −0.513529 −0.159076 0.095*
O4 −0.0454 (4) −0.5134 (4) 0.1040 (2) 0.0642 (9)
O5 0.2225 (4) −0.0137 (4) 0.2664 (3) 0.0764 (11)
O6 0.1304 (4) 0.1587 (4) 0.2506 (3) 0.0697 (10)
C1 0.1316 (6) 0.0283 (6) 0.2298 (4) 0.0592 (13)
C2 0.0138 (5) −0.0763 (5) 0.1559 (3) 0.0544 (12)
C3 −0.0712 (5) −0.0289 (5) 0.1024 (3) 0.0546 (13)
H3A −0.056226 0.067490 0.111385 0.066*
C4 −0.1803 (5) −0.1276 (5) 0.0345 (3) 0.0516 (12)
C5 −0.2021 (5) −0.2743 (5) 0.0201 (3) 0.0459 (11)
C6 −0.1127 (5) −0.3201 (5) 0.0751 (3) 0.0476 (11)
C7 −0.0055 (5) −0.2206 (5) 0.1412 (3) 0.0528 (12)
H7 0.053706 −0.251122 0.175771 0.063*
C8 −0.1317 (5) −0.4754 (5) 0.0615 (3) 0.0475 (11)
C9 −0.3197 (5) −0.3804 (5) −0.0484 (3) 0.0466 (11)
C10 −0.3459 (5) −0.5308 (5) −0.0568 (3) 0.0453 (11)
C11 −0.4637 (5) −0.6348 (5) −0.1179 (3) 0.0515 (12)
C12 −0.4864 (6) −0.7788 (5) −0.1255 (3) 0.0588 (13)
H12 −0.562099 −0.845942 −0.165924 0.071*
C13 −0.3970 (6) −0.8214 (5) −0.0733 (4) 0.0646 (14)
H13 −0.413807 −0.917225 −0.078955 0.078*
C14 −0.2816 (5) −0.7233 (5) −0.0120 (3) 0.0572 (13)
H14 −0.222682 −0.754066 0.022566 0.069*
C15 −0.2551 (5) −0.5790 (5) −0.0028 (3) 0.0469 (11)
C16 0.2689 (5) 0.2008 (5) 0.4754 (3) 0.0532 (12)
C17 0.1436 (7) 0.1917 (8) 0.5189 (5) 0.096 (2)
H17 0.067122 0.216950 0.495724 0.115*
C18 0.1283 (8) 0.1451 (9) 0.5975 (5) 0.109 (3)
H18 0.041457 0.138087 0.624719 0.130*
C19 0.2387 (7) 0.1105 (7) 0.6340 (4) 0.0856 (19)
H19 0.228699 0.081017 0.686577 0.103*
C20 0.3650 (8) 0.1191 (8) 0.5930 (5) 0.096 (2)
H20 0.441213 0.095114 0.617667 0.115*
C21 0.3811 (6) 0.1644 (7) 0.5130 (4) 0.0790 (17)
H21 0.467616 0.169688 0.485624 0.095*
C22 0.5089 (5) 0.2908 (5) 0.3070 (3) 0.0517 (12)
C23 0.5587 (6) 0.1718 (6) 0.2731 (4) 0.0706 (15)
H23 0.497147 0.082055 0.268376 0.085*
C24 0.6997 (7) 0.1871 (7) 0.2464 (5) 0.0884 (19)
H24 0.731389 0.107392 0.224410 0.106*
C25 0.7928 (7) 0.3191 (7) 0.2522 (4) 0.0786 (17)
H25 0.886832 0.328223 0.234707 0.094*
C26 0.7454 (6) 0.4375 (6) 0.2842 (4) 0.0676 (15)
H26 0.807367 0.526465 0.287382 0.081*
C27 0.6050 (6) 0.4243 (5) 0.3117 (3) 0.0578 (13)
H27 0.574545 0.504740 0.333487 0.069*
C28 0.2494 (5) 0.4759 (5) 0.3768 (3) 0.0519 (12)
C29 0.2515 (6) 0.5409 (6) 0.3061 (4) 0.0651 (14)
H29 0.265497 0.492744 0.247970 0.078*
C30 0.2335 (6) 0.6741 (6) 0.3208 (5) 0.0788 (18)
H30 0.236051 0.714688 0.273037 0.095*
C31 0.2116 (7) 0.7473 (6) 0.4070 (5) 0.086 (2)
H31 0.201433 0.837709 0.417363 0.103*
C32 0.2051 (7) 0.6852 (7) 0.4774 (5) 0.093 (2)
H32 0.188321 0.732985 0.534917 0.112*
C33 0.2237 (7) 0.5502 (6) 0.4620 (4) 0.0725 (16)
H33 0.218859 0.509296 0.509717 0.087*

1 Source of material

1,8-Dihydroxy-3-carboxyanthraquinone (0.284 g, 1 mmol) and sodium ethoxide (0.068 g, 1 mmol) were dissolved in 30 mL of methanol in a Schlenk flask and stirred for 30 min. Subsequently, triphenyltin chloride (0.385 g, 1 mmol) was introduced, and the reaction mixture was stirred at room temperature for 12 h. After filtration, the solvent in the filtrate was gradually evaporated under vacuum until a solid product formed. This solid was recrystallized from methanol, resulting in the formation of orange crystals with a yield of 68 %.

2 Experimental details

The structure was solved by Direct Methods with the SHELXS program. Hydrogen atoms were positioned geometrically (C–H = 0.93–0.98 Å). Their U iso values were set to 1.2 U eq or 1.5 U eq of the parent atoms.

3 Comment

Organotin compounds have drawn growing interest owing to their diverse structures and widespread applications. 5 For instance, they participate in the synthesis of many complex organic molecules, including drugs, pesticides, and functional compounds. 6 They also serve as additives or catalysts for polymer modification and functionalization. 7 Furthermore, some organotin carboxylates exhibit biological activities such as antimicrobial, anticancer, and antiviral properties. 8 With increasing understanding of the structure-property relationships of organotin carboxylates, researchers are actively designing and developing novel compounds to expand their application scope.

In this study, we synthesized a new organotin carboxylate compound C33H22O6Sn by reacting 1, 8-dihydroxy-3-carboxyanthraquinone with triphenyltin chloride. The title complex is a monomer with one deprotonated ligand and one triphenyltin unit. The tin atom is linked to three phenyl groups and one oxygen atom, leading to a distorted tetrahedral geometry. The bond length Sn1–O6 [2.118(3) Å] is smaller than the sum of covalent radii of Sn and O [2.13 Å], which proves the existence of strong covalent bond between Sn and O. 9 The angle O6–Sn1–C28 96.92(16)° deviates significantly from the ideal tetrahedral coordination angle due to the interaction of O5 with the Sn atom. All these values are similar to the reported analogue compounds. 10 , 11 , 12 , 13 , 14 , 15 , 16

Corresponding author: Shuang Lü, State Key Laboratory for Macromolecule Drugs and Large-Scale Manufacturing, School of Pharmaceutical Sciences, Liaocheng University, Liaocheng 252059, P.R. China, E-mail:

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

  2. Research funding: This research was supported by Shandong Provincial Natural Science Foundation under Grant ZR2020MB019.

  3. Competing interests: The authors declare no conflicts of interest regarding this article.

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Received: 2024-06-25
Accepted: 2024-07-30
Published Online: 2024-08-07
Published in Print: 2024-10-28

© 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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  17. The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3
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  41. Crystal structure of (3,6-di(2-pyridyl)-4-methylphenyl pyridazine-k 2 N,N′)-bis(1-phenyl-pyrazole-κ 2 C,N) iridium(III) hexafluorophosphate, C39H29F6IrN8P
  42. Crystal structure of 1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene]thiocarbonohydrazide dimethyl sulfoxide monosolvate, C17H18N4O2S·C2H6OS
  43. Crystal structure of (S)-4-(2-(4-(2-acetyl-5-chlorophenyl)-3-methoxy-6-oxopyridazin-1(6H)-yl)-3-phenylpropanamido)benzoic acid monohydrate, C29H26ClN3O7
  44. The crystal structure of 1,3-bis(2,4-dinitro-1H-imidazol-1-yl)propane
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  47. The crystal structure of (Z)-3′-(2-(1-(3,4-dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylicacid ─ methanol (1/1), C26H26N4O5
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  50. The crystal structure of trichlorobis(pyridine-2,6-dithio-κS-carbomethylamido)antimony(III), [SbCl3(C9H11N3S2)2]
  51. Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn
  52. The crystal structure of (E)-4-(2-(pyridin-4-ylmethylene)hydrazine-1-carbonyl)pyridin-1-ium-2-olate dihydrate, C12H14N4O4
  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N′)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2′-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
https://doi.org/10.1515/ncrs-2024-0267
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Articles in the same Issue

  1. Frontmatter
  2. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
  5. Hydrogen bonding and π⋅⋅⋅halogen interactions in the crystal structure of bis(theophyllinium) hexachloridoplatinate(IV) monohydrate
  6. The crystal structure of 6-amino-2-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  7. Crystal structure of poly[(μ4-(3-amino-1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ 4 N:O:O':O')(1-methylpyrroldin-2-one-κ1O)dicopper(II)] – 1-methylpyrroldin-2-one (1/3), C40H48Cu2N12O12
  8. The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
  9. Crystal structure of poly[tetraaqua-bis(μ2-5-bromoisophthalato-κ3O,O′:O″)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)dicadmium(II)] dihydrate
  10. Crystal structure of (5R,6S,E)-5-acetoxy-2-methyl-6-((2aR,3R,5aS,5bS,11aR,12aS)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-3-yl)hept-2-enoic acid, C32H48O5
  11. The crystal structure of poly[diaqua-bis(μ2 -thiocyanato-κ2N:O)cobalt(II) monohydrate
  12. The crystal structure of 1,3,5-tri(1H-imidazol-1-yl)benzene–2,3,5,6-tetrachlorobenzene-1,4-dicarboxylic acid (1/1)
  13. Crystal structure of dichlorido-bis(1-[(2-ethyl-benzimidazole-1-yl)methyl]-1H–benzotriazole) cadmium(II), C32H32CdN10OCl2
  14. The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
  15. Crystal stucture of 3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide
  16. Crystal structure of bis(μ-benzeneselenolato)-(tetracarbonyl)-{μ-[N-(diphenylphosphanyl)-N-(3-ethynylphenyl)-P,P-diphenylphosphinous amide]} diiron, C48H35Fe2NO4P2Se2
  17. The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3
  18. The crystal structure of poly[hexaqua-tetrakis(μ4-pyridine-2,4-dicarboxylate-κ5N: O: O′: O″: O‴)-bi(μ2-pyridine-2,4-dicarboxylate-κ3N: O: O′)-digadolinium(III)tricopper (II)], [Gd2Cu3(C7H3NO4)6(H2O)6] n
  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
  20. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-carboxy-6-nitrobenzoate monohydrate, C24H25FN4O10
  21. Crystal structure of dichlorido-(1-((3,5-dimethyl-2,3-dihydro-1H-1,2,3-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-k1N)zinc(II), C22H24ZnN12Cl2
  22. The crystal structure of (3-chlorothiophene-2-carboxylato-κ2O, O′)-(2,2′-dipyridyl-κ2N,N′)lead(II), C20H12Cl2N2O4S2Pb
  23. Synthesis and crystal structure of (Z)-4-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, C19H14FN5O
  24. The crystal structure of the coordination compound catena-poly[(18-crown-6-ether-κ6O6)(4,5-dinitroimidazolato-κ1O)potassium(I)]
  25. Crystal structure of 7-(diethylamino)-3-(trifluoroacetyl)-2H-chromen-2-one, C15H14F3NO3
  26. Crystal structure of dichlorido-1-[(2-ethylimidazole-1-yl)methyl]-1H–benzotriazole κ1N zinc(II), C24H26ZnN10Cl2
  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
  28. Crystal structure of catena-poly[bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-k3-O,O′:O″)hexaqua-dicobalt tetrahydrate], C26H36N4O20Co2
  29. Crystal structure of thiocyanate-κ1N-bis(μ1-2,6-diformyl-4-methylphenol oxime-κ2N,O)-manganese(III) acetonitrile solvate, C21H21MnN6O6S
  30. The crystal structure of pyrrolidin-1-yl pivalate, C9H13NO4
  31. The crystal structure of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(1,4-dimethoxybenzene), C30H28O4
  32. Crystal structure of bis(benzyltrimethylammonium) tetrathiotungstate(VI), {(C6H5CH2)(CH3)3N}2[WS4]
  33. The crystal structure of ethyl (Z)-2-(ethoxymethylene)-3-oxobutanoate, C9H14O4
  34. The crystal structure of (E)-6-bromo-3,5-dimethyl-2-(1-phenylprop-1-en-2-yl)-3Himidazo[4,5b]pyridine, C17H16BrN3
  35. Crystal structure of (3S,3′S,4R,4′S)-3′-(furan-3-yl)-3-hydroxy-4′-methyl-3,5,6′,7′-tetrahydro-1H,3′H-4,5′-spirobi[isobenzofuran]-1,1′(4′H)-dione-methanol (1/1), C21H22O7
  36. Cocrystal structure of progesterone-isophthalic acid, C25H33O4
  37. The crystal structure of 3-(6-fluoro-1H-indol-3-yl)-1-methylquinoxalin-2(1H)-one, C17H12FN3O
  38. Crystal structure of S-(4-carboxybutyl)- l -cysteine
  39. The cocrystal of 2,2′-(hydrazine-1,1-diyl)bis(1H-imidazole-4,5-dicarbonitrile)– methanol (2/3)
  40. Crystal structure of (1′R,2′S,4′R,6′S)-4,6-dihydroxy-1′,8′,8′-trimethyl-3-(3-methylbutanoyl)-4′,8′,6′,1′,7,2′-hexahydro-1H-4′,6′-methanoxanthene-8-carbaldehyde, C23H30O5
  41. Crystal structure of (3,6-di(2-pyridyl)-4-methylphenyl pyridazine-k 2 N,N′)-bis(1-phenyl-pyrazole-κ 2 C,N) iridium(III) hexafluorophosphate, C39H29F6IrN8P
  42. Crystal structure of 1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene]thiocarbonohydrazide dimethyl sulfoxide monosolvate, C17H18N4O2S·C2H6OS
  43. Crystal structure of (S)-4-(2-(4-(2-acetyl-5-chlorophenyl)-3-methoxy-6-oxopyridazin-1(6H)-yl)-3-phenylpropanamido)benzoic acid monohydrate, C29H26ClN3O7
  44. The crystal structure of 1,3-bis(2,4-dinitro-1H-imidazol-1-yl)propane
  45. Crystal structure of 4-chlorobenzyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H19ClO3
  46. Crystal structure of 1-(5-(benzo[d][1,3]dioxol-5-yl)-4-benzyl-1-(4-bromophenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethan-1-one, C24H20BrN3O3
  47. The crystal structure of (Z)-3′-(2-(1-(3,4-dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylicacid ─ methanol (1/1), C26H26N4O5
  48. Crystal structure of (S)-1-phenylpropan-1-aminium (S)-(1-phenylpropyl)carbamate C19H26N2O2
  49. Synthesis and crystal structure of methyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, C18H16BrN3O2S
  50. The crystal structure of trichlorobis(pyridine-2,6-dithio-κS-carbomethylamido)antimony(III), [SbCl3(C9H11N3S2)2]
  51. Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn
  52. The crystal structure of (E)-4-(2-(pyridin-4-ylmethylene)hydrazine-1-carbonyl)pyridin-1-ium-2-olate dihydrate, C12H14N4O4
  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N′)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2′-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
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