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The crystal structure of 1,3,5-tris(dibromomethyl)benzene, C9H6Br6

  • Chao-Bo Yang , Jia-Lu Chen , Tian-Yu Zhang and Kai-Long Zhong ORCID logo EMAIL logo
Published/Copyright: December 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

C9H6Br6, hexagonal, P63/m (no. 176), a = 8.8911(3) Å, c = 10.6847(5) Å, V = 731.48(6) Å3, Z = 2, R gt (F) = 0.0441, wR ref (F2) = 0.1094, T = 293 K.

CCDC no.: 2314064

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: Colorless needle
Size: 0.35 × 0.15 × 0.12 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 16.4 mm−1
Diffractometer, scan mode: Bruker Smart Apex, φ and ω
θmax, completeness: 27.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 6752, 593, 0.049
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 508
N(param)refined: 28
Programs: Bruker [1], SHELX [2, 3]
Table 2:

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

Atom x y z Uiso*/Ueq
Br1 −0.09994 (9) 0.63741 (11) 0.89771 (6) 0.0478 (3)
C1 0.2856 (12) 0.7929 (10) 0.7500 0.0339 (19)
H1A 0.2534 0.8776 0.7500 0.041*
C2 0.1596 (10) 0.6186 (11) 0.7500 0.037 (2)
C3 −0.0323 (11) 0.5583 (12) 0.7500 0.0336 (18)
H3A −0.0964 0.4310 0.7500 0.040*

1 Source of material

All chemicals were obtained from commercial sources and were used as purchased. A mixture of 1,3,5-trimethylbenzene (2.1 mL, 15 mmol), N-bromosuccinimide (16.0 g 90 mmol), dibenzoyl peroxide (0.72 g, 3 mmol) and benzene (120 mL) was stirred at 80 °C for 30 min. After refluxing under nitrogen for 4 h, the solution was allowed to cool and was filtered. The organic phase was concentrated under reduced pressure, then the crude products were purified by flash column chromatography. Colorless needle crystals of the title compound were obtained by slow evaporation of a solution in ethanol/hexane at room temperature. 1 H NMR (500 MHz, Chloroform-d): δ 7.75.08 (s, 3H), 6.66 (s, 3H).

2 Experimental details

Data were integrated by using the Saint program [1], absorption corrections were applied using Sadabs program [1], the structure was solved with the SHELXS-2014 [2] program and refined with the SHELXL-2018 [3] software package. H atoms bound to C and N atoms were positioned geometrically and allowed to ride on their parent atoms, with C–H = 0.93 Å (phenyl) or 0.98 Å (methyl) and Uiso(H) = 1.2Ueq(C).

3 Comment

Benzyl bromide moieties are prominent skeletons that are ubiquitous in natural products, bioactive molecules, and pharmaceuticals [4], [5], [6]. Bromide chemistry has been recognized as one of the most attractive functionalities in organic synthesis [7], [8], [9], [10]. 1,3,5-Tris(dibromomethyl)benzene is widely used in organic reactions but difficult to synthesize [11]. Therefore, synthesizing the tris(dibromomethyl)benzene and conducting subsequent derivative applications is of great significance.

Single-crystal structure analysis revealed that the title compound crystallized in the hexagonal space group, the asymmetric unit consists of one-sixth 1,3,5-tris(dibromomethyl)benzene molecule. The C–Br bond length is 1.942(5) Å and the Br–C–Br angle is 108.7(4)°, these results are similar to that observed in a previously reported dibromomethyl-substituted benzene compounds, namely 1,3-dibromo-5-(dibromomethyl)benzene, 1,4-dibromo-2,5-bis(bromomethyl)benzene, 1,4-dibromo-2-(dibromomethyl)benzene, 1,2-bis(dibromomethyl)benzene, 1-(bromomethyl)-2-(dibromomethyl)benzene and 1,3-bis(dibromomethyl)benzene [6]. The 1,3,5-tris(dibromomethyl)benzene molecule lies on a mirror plane and a threefold rotation axis. The planes defined the terminal dibromomethyl groups (C3/Br/Br iii and C3 i /Br i /Br vi , C3 ii /Br ii /Br vii ) [symmetry codes: (i) −y + 1, x − y + 1, z; (ii) −x + y, -x + 1, z; (iii) x, y, −z + 3/2; (vi) −y + 1, x − y + 1, −z + 3/2; (vii) −x + y, -x + 1, −z + 3/2] and the least-squares plane of the central benzene ring is perpendicular. The dihedral angles between pairs of symmetric terminal imidazole rings are 60.0° between C3/Br/Br iii and C3 i /Br i /Br vi , C3/Br/Br iii and C3 ii /Br ii /Br vii , and C3 i /Br i /Br vi and C3 ii /Br ii /Br vii . In the solid state structure, numerous weak C3–H3A⋯Br1 iv and C3–H3A⋯Br1 iv [symmetry codes: (iv) −x + y − 1, −x, z; (v) −x + y − 1, −x, −z + 3/2] hydrogen-bonding interactions result in a two-dimensional supramolecular layer extending in the ab plane. Within the sheet, the R ( 9 ) 3 3 and the R ( 21 ) 3 3 motifs can be discerned.

Corresponding author: Kai-Long Zhong, School of Life and Health, Nanjing Polytechnic Institute, Nanjing, 210048, People’s Republic of 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 work was financially supported by Key Scientific Research Foundation of Nanjing Polytechnic Institute (No. NJPI-2022-04), Innovation and Entrepreneurship Cultivation Project for Vocational Students in Jiangsu Province.

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

References

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Received: 2023-11-11
Accepted: 2023-12-13
Published Online: 2023-12-29
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.

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
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https://doi.org/10.1515/ncrs-2023-0498
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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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