Home Crystal structure of N2,N6-bis(2-(((Z)-5-bromo-2-hydroxybenzylidene)amino) phenyl)pyridine-2,6-dicarboxamide, C33H23Br2N5O4
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Crystal structure of N2,N6-bis(2-(((Z)-5-bromo-2-hydroxybenzylidene)amino) phenyl)pyridine-2,6-dicarboxamide, C33H23Br2N5O4

  • Wen-Ze Zhao ORCID logo EMAIL logo , Lei Zhang and Na Zhang
Published/Copyright: November 29, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 1

Abstract

C33H23Br2N5O4, triclinic, P1̄ (no. 2), a = 10.649(3) Å, b = 11.244(3) Å, c = 14.301(4) Å, α = 68.254(7)°, β = 72.939(7)°, γ = 81.125(7)°, V = 1518.5(7) Å3, Z = 2, Rgt(F) = 0.0514, wRref(F2) = 0.1327, T = 273(2) K.

CCDC no.: 2308884

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: Brown block
Size: 0.20 × 0.18 × 0.17 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 2.72 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 25.0°, 98 %
N(hkl)measured, N(hkl)unique, Rint: 12114, 5231, 0.059
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2863
N(param)refined: 399
Programs: Olex2 [1], Bruker [2], SHELX [3], Diamond [4]
Table 2:

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

Atom x y z Uiso*/Ueq
Br1 0.08924 (5) 0.65586 (6) 1.00304 (6) 0.1123 (3)
Br2 0.32398 (6) 0.92901 (5) 0.50625 (6) 0.0987 (3)
O1 0.5868 (3) 0.3468 (3) 0.8911 (2) 0.0584 (8)
H1 0.6418 0.3915 0.8425 0.088*
O2 1.1052 (3) 0.3544 (3) 0.6714 (3) 0.0758 (10)
O3 0.6299 (3) 0.4212 (3) 0.6078 (2) 0.0550 (8)
H3 0.5856 0.3658 0.6565 0.082*
O4 0.6280 (3) −0.0896 (3) 0.8121 (3) 0.0772 (10)
N1 0.6907 (3) 0.5610 (3) 0.7584 (3) 0.0451 (9)
N2 0.8920 (3) 0.4192 (3) 0.6746 (3) 0.0490 (9)
H2 0.8150 0.3930 0.6873 0.059*
N3 0.8292 (3) 0.1690 (3) 0.7443 (3) 0.0481 (9)
N4 0.5708 (3) 0.1108 (3) 0.8181 (3) 0.0541 (10)
H4 0.6017 0.1837 0.8037 0.065*
N5 0.4164 (3) 0.3208 (3) 0.7444 (2) 0.0408 (8)
C1 0.2536 (4) 0.4299 (5) 1.0137 (4) 0.0577 (12)
H1A 0.1805 0.3893 1.0636 0.069*
C2 0.3672 (4) 0.3587 (4) 0.9890 (3) 0.0542 (12)
H2A 0.3712 0.2703 1.0221 0.065*
C3 0.4769 (4) 0.4201 (4) 0.9137 (3) 0.0422 (10)
C4 0.4709 (4) 0.5526 (4) 0.8636 (3) 0.0412 (10)
C5 0.5810 (4) 0.6196 (4) 0.7849 (3) 0.0454 (10)
H5 0.5719 0.7079 0.7527 0.054*
C6 0.8001 (4) 0.6273 (4) 0.6828 (3) 0.0441 (10)
C7 0.9040 (4) 0.5531 (4) 0.6425 (3) 0.0453 (10)
C8 0.9911 (4) 0.3299 (5) 0.6867 (3) 0.0538 (12)
C9 0.9564 (4) 0.1938 (4) 0.7185 (3) 0.0493 (11)
C10 0.8016 (4) 0.0463 (4) 0.7717 (3) 0.0497 (11)
C11 0.6578 (5) 0.0157 (4) 0.8026 (3) 0.0548 (12)
C12 0.4333 (4) 0.1017 (4) 0.8562 (3) 0.0448 (10)
C13 0.3535 (4) 0.2115 (4) 0.8224 (3) 0.0414 (10)
C14 0.3583 (4) 0.4319 (4) 0.7197 (3) 0.0426 (10)
H14 0.2709 0.4425 0.7544 0.051*
C15 0.4248 (4) 0.5415 (4) 0.6392 (3) 0.0381 (9)
C16 0.5573 (4) 0.5333 (4) 0.5868 (3) 0.0405 (10)
C17 0.6169 (4) 0.6420 (4) 0.5109 (3) 0.0511 (11)
H17 0.7048 0.6361 0.4755 0.061*
C18 0.5481 (5) 0.7576 (4) 0.4874 (3) 0.0562 (12)
H18 0.5888 0.8300 0.4366 0.067*
C19 0.2472 (4) 0.5601 (5) 0.9656 (4) 0.0603 (13)
C20 0.3531 (4) 0.6221 (4) 0.8913 (3) 0.0536 (12)
H20 0.3471 0.7107 0.8591 0.064*
C21 1.0567 (5) 0.0995 (5) 0.7211 (4) 0.0686 (14)
H21 1.1438 0.1203 0.7036 0.082*
C22 1.0256 (5) −0.0252 (5) 0.7497 (4) 0.0796 (17)
H22 1.0913 −0.0904 0.7518 0.096*
C23 0.8967 (5) −0.0523 (5) 0.7751 (4) 0.0696 (14)
H23 0.8734 −0.1361 0.7944 0.084*
C24 0.4177 (5) 0.7659 (4) 0.5397 (4) 0.0548 (12)
C25 0.3556 (4) 0.6608 (4) 0.6144 (3) 0.0478 (11)
H25 0.2676 0.6684 0.6488 0.057*
C26 0.2184 (4) 0.2061 (4) 0.8665 (3) 0.0532 (12)
H26 0.1642 0.2791 0.8465 0.064*
C27 0.1637 (5) 0.0952 (5) 0.9387 (4) 0.0619 (13)
H27 0.0732 0.0933 0.9669 0.074*
C28 0.2430 (5) −0.0134 (5) 0.9695 (4) 0.0643 (13)
H28 0.2056 −0.0891 1.0174 0.077*
C29 0.3767 (5) −0.0102 (4) 0.9298 (3) 0.0585 (12)
H29 0.4299 −0.0831 0.9523 0.070*
C30 1.0172 (4) 0.6125 (5) 0.5700 (3) 0.0544 (12)
H30 1.0869 0.5635 0.5430 0.065*
C31 1.0248 (5) 0.7427 (5) 0.5390 (4) 0.0624 (13)
H31 1.0999 0.7817 0.4911 0.075*
C32 0.9227 (5) 0.8156 (5) 0.5780 (4) 0.0684 (14)
H32 0.9288 0.9038 0.5563 0.082*
C33 0.8112 (5) 0.7592 (4) 0.6491 (4) 0.0589 (12)
H33 0.7424 0.8098 0.6750 0.071*

1 Source of materials

In a 100 mL three necked flask, N2,N6-bis(2-aminophenyl)pyridine-2,6-dicarboxamide (0.69 g, 2 mmol), 5-bromo-2-hydroxybenzaldehyde (0.80 g, 4 mmol) and 60 mL ethanol solution were added, heated and refluxed for 7 h, cooled to room temperature to precipitate a yellow powder, filtered under reduced pressure, washed with ethanol for 4 times, and dried in vacuum. A yellow solid weighing 1.03 g was obtained with a yield of 72 %. Take 0.1 g of solid into a 25 mL beaker, add 10 mL chloroform, stir and dissolve it, let it stand still at room temperature and volatilize it naturally for 9 days, and then precipitate crystals.

2 Experimental details

Using Olex2 [1], the structure was solved using charge flipping and refined with the ShelXL [3] refinement. All hydrogen atoms were positioned geometrically, with the d(C–H) = 0.97–0.99 Å, Uiso(H) = 1.2 times Ueq(C) and Uiso(H) = 1.5 times Ueq(O).

3 Comment

Schiff bases are a class of organic compounds formed by the condensation of amines and active carbonyl groups, which contain imine or imine characteristic groups. They are widely used in metal ion recognition and construction of coordination compounds [5]. Schiff bases and their metal complexes have important application prospects in catalysis, analytical chemistry, medicine, corrosion, photochromism, and other fields [6, 7]. N2,N6-bis (2-aminophenyl) pyridine-2,6-dicarboxamide is widely used for metal ion recognition and the construction of Schiff base complexes due to its presence of multiple nitrogen atoms and the presence of multiple coordination atoms in the Schiff base formed by condensation reaction with aldehydes [8, 9]. The single crystal structure shows that the two amino groups have undergone a condensation reaction with the aldehyde group of 5-bromo-2-hydroxybenzaldehyde. The bond length of N2=C7 is 1.416(5) Å, and the bond length of N4=C12 is 1.411(5) Å [10, 11]. There are O1–H1⋯N1, O3–H3⋯N5, N2–H2⋯O3 and N4–H4⋯O1 intramolecular hydrogen bonds in the molecule.

Corresponding author: Wen-Ze Zhao, Shandong Vocational College of Industry, Zibo, Shandong, 256414, People’s Republic of China, E-mail:

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

  2. Research funding: None declared.

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

References

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Received: 2023-10-03
Accepted: 2023-11-18
Published Online: 2023-11-29
Published in Print: 2024-02-26

© 2023 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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  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of poly[diaqua-(μ4-3,3′-di(1H-1,2,4-triazol-1-yl)-[1,1′-biphenyl]-4,4′-dicarboxylate-N:N′:O:O′)cadmium(II)], C18H14N6O6Cd
  4. Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
  5. The crystal structure of 8-methoxy-2,2-diphenyl-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C29H25BN2O3S
  6. Crystal structure of aqua-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)copper(II) 5-carboxyisophthalate tetrahydrate, C25H50N4CuO11
  7. The crystal structure of 1-(naphthalen-2-ylsulfonyl)-2,2-diphenyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinoline, C31H23BN2O2S
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  9. The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2
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  11. Crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)cadmium(II)]monohydrate, C12H15NO9Cd
  12. Crystal structure of ethyl 2-((4-(3,5-dimethylisoxazol-4-yl)-2,6-difluorophenyl)amino)benzoate, C20H18F2N2O3
  13. The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
  14. The crystal structure of 1,2-bis(2,4-dinitrophenyl) hydrazine, C12H8N6O8
  15. Crystal structure of 1-(2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one, C19H14Cl2N2O3
  16. The crystal structure of 5-amino-5-oxo-4-(1-oxo-4-(2-oxopyrrolidin-1-yl)isoindolin-2-yl)pentanoic acid, C17H19N3O5
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  18. The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
  19. The crystal structure of 3-((tert-butyldiphenylsilyl)methyl)-5,5-diphenyl-6-(p-tolyl) tetrahydro-2H-pyran-2-one, C41H42O2Si
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  21. The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3
  22. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-isopropyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C10H14F6N2P
  23. The crystal structure of 2,2-di(thiophen-3-yl)-1-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C24H19BN2O2S3
  24. Crystal structure of 5-bromo-1-(2-iodobenzoyl)-1H-indole-3-carbaldehyde, C16H9BrINO2
  25. The crystal structure of monocarbonyl-2-carboxypyridinato-κ2N,O-triphenylphosphine-rhodium(I) acetonitrile solvate, C26H20.50N1.50O3PRh
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  30. Synthesis and crystal structure of bis{2-(((4-acetophenone)imino)methyl)-4-fluorophenolato-κ2N,O}zinc(II), C30H22F2N2O4Zn
  31. The crystal structure of poly[(tripyridine-κ3N,N′,N″) μ3-(pyridine-3,4-dicarboxylate-κ3N:O:O′) manganese(II)], C22H22N4O8Mn
  32. The crystal structure of (E)-4-chloro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15ClN2O2
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https://doi.org/10.1515/ncrs-2023-0432
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of poly[diaqua-(μ4-3,3′-di(1H-1,2,4-triazol-1-yl)-[1,1′-biphenyl]-4,4′-dicarboxylate-N:N′:O:O′)cadmium(II)], C18H14N6O6Cd
  4. Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
  5. The crystal structure of 8-methoxy-2,2-diphenyl-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C29H25BN2O3S
  6. Crystal structure of aqua-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)copper(II) 5-carboxyisophthalate tetrahydrate, C25H50N4CuO11
  7. The crystal structure of 1-(naphthalen-2-ylsulfonyl)-2,2-diphenyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinoline, C31H23BN2O2S
  8. Crystal structure of iodido-(η6-benzene) (1-(pyridin-2-yl)-N-(p-fluoro-methanamine)-κ2N,Nʹ)ruthenium(II) hexaflourophosphate, (C18H15F7IN2RuP)
  9. The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2
  10. Crystal structure of tricyclohexyl[4-(4H-1,2,4-triazol-4-yl)-benzoato-κO]tin(IV), C27H39N3O2Sn
  11. Crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)cadmium(II)]monohydrate, C12H15NO9Cd
  12. Crystal structure of ethyl 2-((4-(3,5-dimethylisoxazol-4-yl)-2,6-difluorophenyl)amino)benzoate, C20H18F2N2O3
  13. The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
  14. The crystal structure of 1,2-bis(2,4-dinitrophenyl) hydrazine, C12H8N6O8
  15. Crystal structure of 1-(2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one, C19H14Cl2N2O3
  16. The crystal structure of 5-amino-5-oxo-4-(1-oxo-4-(2-oxopyrrolidin-1-yl)isoindolin-2-yl)pentanoic acid, C17H19N3O5
  17. Crystal structure of N2,N6-bis(2-(((Z)-5-bromo-2-hydroxybenzylidene)amino) phenyl)pyridine-2,6-dicarboxamide, C33H23Br2N5O4
  18. The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
  19. The crystal structure of 3-((tert-butyldiphenylsilyl)methyl)-5,5-diphenyl-6-(p-tolyl) tetrahydro-2H-pyran-2-one, C41H42O2Si
  20. Crystal structure of 9-fluoro-4-(6-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  21. The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3
  22. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-isopropyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C10H14F6N2P
  23. The crystal structure of 2,2-di(thiophen-3-yl)-1-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C24H19BN2O2S3
  24. Crystal structure of 5-bromo-1-(2-iodobenzoyl)-1H-indole-3-carbaldehyde, C16H9BrINO2
  25. The crystal structure of monocarbonyl-2-carboxypyridinato-κ2N,O-triphenylphosphine-rhodium(I) acetonitrile solvate, C26H20.50N1.50O3PRh
  26. Crystal structure of dichlorido-tetrakis(1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1N)manganese(II), C60H68O4N12Cl10Mn
  27. Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi
  28. Crystal structure of langite from Mine du Pradet (France)
  29. The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S
  30. Synthesis and crystal structure of bis{2-(((4-acetophenone)imino)methyl)-4-fluorophenolato-κ2N,O}zinc(II), C30H22F2N2O4Zn
  31. The crystal structure of poly[(tripyridine-κ3N,N′,N″) μ3-(pyridine-3,4-dicarboxylate-κ3N:O:O′) manganese(II)], C22H22N4O8Mn
  32. The crystal structure of (E)-4-chloro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15ClN2O2
  33. Synthesis and crystal structure of bis{2-(tert-butyl)-6-((E)-((4-((E)-1-(methoxyimino) ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II), C40H46CoN4O4
  34. Crystal structure of tetraaqua-[(1-(carboxymethyl)-1H-pyrazole-3-carboxylato-κ2N,O)cobalt(II)], C6H12CoN2O8
  35. (6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3′,4′]cycloocta [1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol, C22H26O6
  36. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)benzoic acid, C18H14Cl2N2O3
  37. Crystal structure of (5aS,6aS,8aR,9R,11aS, 11bS,13R,13aS)-1,1,8a,11a-tetramethyl-9-((S)-1-((S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3-oxo-1,7,8,8a,9,10,11,11a,11b,12,13,13a-dodecahydro-3H,6H-cyclopenta[5,6]cyclopropa[1,8a]naphtho[2,1-c]oxepin-13-yl acetate, C32H44O6
  38. Crystal structure of catena-poly[triaqua-(μ2-1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-O,O′:O″)cobalt(II)], C12H12N2O8Co
  39. Crystal structure of 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester, C17H13F4NO4
  40. Crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3-methoxybenzoate, C13H16O6
  41. Crystal structure of 4-bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, C13H7BrClF3N2
  42. The crystal structure of triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ3N,O,O)nickel(II) monohydrate, C12H15NO9Ni
  43. Crystal structure of dihydroxy(2,4,6-triisopro-pylphenyl)telluronium trifluoromethanesulfonate, C16H25F3O5STe
  44. The crystal structure of 1-(carboxymethyl)-1H-imidazole 3-oxide
  45. The crystal structure of 1,3,5-tris(dibromomethyl)benzene, C9H6Br6
  46. Crystal structure of (Z)-3-(4-methoxyphenyl)-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-N-phenylthiazol-2(3H)-imine, C25H21N5OS
  47. Crystal structure of (Z)-3-(3-(4-hydroxyphenyl)-2-(phenylimino)-2,3-dihydrothiazol-4-yl)-2H-chromen-2-one, C24H16N2O3S
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