Home Physical Sciences Crystal structure of (Z)-3-(3-(4-hydroxyphenyl)-2-(phenylimino)-2,3-dihydrothiazol-4-yl)-2H-chromen-2-one, C24H16N2O3S
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Crystal structure of (Z)-3-(3-(4-hydroxyphenyl)-2-(phenylimino)-2,3-dihydrothiazol-4-yl)-2H-chromen-2-one, C24H16N2O3S

  • Bakr F. Abdel-Wahab , Saud A. Alanazi , Emad Yousif , Benson M. Kariuki and Gamal A. El-Hiti 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

C24H16N2O3S, triclinic, P 1 ‾ (no. 2), a = 6.7738(3) Å, b = 11.6072(6) Å, c = 13.6060(9) Å, α = 69.197(6)°, β = 87.025(5)°, γ = 76.990(4)°, V = 973.90(10) Å3, Z = 2, R gt (F) = 0.0482, wR ref (F2) = 1191, T = 293(2) K.

CCDC no.: 2314056

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.

Figure 1: Oretep representation of C24H16N2O3S showing 50 % probability ellipsoids.
Figure 1:

Oretep representation of C24H16N2O3S showing 50 % probability ellipsoids.

Table 1:

Data collection and handling.

Crystal: Needle
Size: 0.51 × 0.18 × 0.09 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.20 mm−1
Diffractometer, scan mode: SuperNova, ω
θmax, completeness: 29.8°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 9085, 4643, 0.027
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 3456
N(param)refined: 272
Programs: CrysAlisPro [1], SHELX [2], WinGX/ORTEP [3], CHEMDRAW [4]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.3230 (3) 0.09965 (18) 0.71824 (15) 0.0383 (4)
C2 0.1327 (3) 0.0800 (2) 0.75093 (17) 0.0472 (5)
H2 0.021607 0.118125 0.704308 0.057*
C3 0.1077 (4) 0.0035 (2) 0.85323 (19) 0.0597 (6)
H3 −0.020624 −0.009146 0.874940 0.072*
C4 0.2710 (4) −0.0540 (2) 0.92320 (18) 0.0599 (6)
H4 0.253591 −0.105995 0.991549 0.072*
C5 0.4589 (4) −0.0337 (2) 0.89088 (17) 0.0545 (6)
H5 0.569540 −0.071982 0.937827 0.065*
C6 0.4864 (3) 0.0429 (2) 0.78950 (16) 0.0453 (5)
H6 0.614734 0.056533 0.768821 0.054*
C7 0.3107 (3) 0.15544 (17) 0.53638 (15) 0.0341 (4)
C8 0.2202 (3) 0.07071 (19) 0.40507 (16) 0.0410 (5)
H8 0.181907 0.025773 0.367486 0.049*
C9 0.2674 (3) 0.18276 (18) 0.36010 (15) 0.0352 (4)
C10 0.2666 (3) 0.25009 (18) 0.24588 (15) 0.0372 (4)
C11 0.4554 (3) 0.2818 (2) 0.19874 (16) 0.0417 (5)
C12 0.2898 (3) 0.3519 (2) 0.02815 (16) 0.0452 (5)
C13 0.1133 (3) 0.31867 (19) 0.07210 (15) 0.0419 (5)
C14 0.1051 (3) 0.26890 (19) 0.18428 (15) 0.0399 (4)
H14 −0.014458 0.249166 0.215191 0.048*
C15 0.3129 (4) 0.3981 (3) −0.07901 (18) 0.0638 (7)
H15 0.432265 0.421168 −0.107204 0.077*
C16 0.1541 (4) 0.4092 (3) −0.14293 (19) 0.0754 (8)
H16 0.167762 0.438865 −0.215479 0.090*
C17 −0.0245 (4) 0.3776 (3) −0.10238 (19) 0.0680 (7)
H17 −0.130147 0.386257 −0.147271 0.082*
C18 −0.0465 (3) 0.3334 (2) 0.00444 (17) 0.0538 (6)
H18 −0.167949 0.313113 0.031971 0.065*
C19 0.3226 (3) 0.36330 (17) 0.40678 (14) 0.0342 (4)
C20 0.5033 (3) 0.40177 (19) 0.39629 (16) 0.0418 (5)
H20 0.625552 0.343916 0.401233 0.050*
C21 0.5014 (3) 0.52668 (19) 0.37840 (17) 0.0447 (5)
H21 0.622755 0.553395 0.370296 0.054*
C22 0.3191 (3) 0.61256 (18) 0.37248 (15) 0.0416 (5)
C23 0.1393 (3) 0.57410 (19) 0.37911 (17) 0.0451 (5)
H23 0.016550 0.632289 0.371565 0.054*
C24 0.1414 (3) 0.44943 (18) 0.39693 (15) 0.0402 (5)
H24 0.019877 0.423325 0.402319 0.048*
N1 0.3543 (2) 0.18229 (15) 0.61556 (12) 0.0395 (4)
N2 0.3184 (2) 0.23212 (14) 0.43302 (12) 0.0349 (4)
O1 0.6119 (2) 0.26286 (16) 0.24484 (12) 0.0547 (4)
O2 0.4518 (2) 0.33949 (14) 0.09103 (11) 0.0494 (4)
O3 0.3099 (2) 0.73376 (13) 0.36354 (15) 0.0613 (5)
H3A 0.424333 0.742938 0.370313 0.092*
S1 0.23759 (8) 0.01755 (5) 0.54105 (4) 0.04174 (15)

1 Source of material

A mixture of 4-hydroxyaniline (0.55 g, 5 mmol) and phenyl isothiocyanate (0.68 g, 5 mmol) in EtOH (15 mL) was refluxed for 15 min. 3-(2-Bromoacetyl)-2H-chromen-2-one (1.33 g, 5 mmol) was added, and the mixture was refluxed for 4 h. The mixture was left overnight, and the solid formed was filtered, dried, and recrystallized from DMF to give the title heterocycle in 82 % yield, mp 179–181 °C. IR (KBr; cm−1): 3121, 1610, 1517. 1H NMR (δ): 6.56 (s, 1H, thiazolyl), 6.67 (d, 8.6 Hz, 2H, Ar), 6.87 (d, 7.6 Hz, 2H, Ar), 6.98 (t, 7.2 Hz, 1H, Ar), 7.10 (d, 8.6 Hz, 2H, Ar), 7.26–7.36 (m, 4H, Ar), 7.59 (t, 7.2 Hz, 1H, Ar), 7.66 (d, 7.6 Hz, 1H, Ar), 8.15 (s, 1H, Ar), 9.58 (s, exch., 1H, OH). 13C NMR (δ): 100.7, 115.7, 116.7, 118.8, 119.8, 121.5, 123.4, 125.5, 128.9, 129.4, 130.1, 130.5, 133.2, 134.6, 145.0, 152.0, 153.8, 157.3, 158.4, 159.3. Anal. calcd. for C24H16N2O3S (412.46): C, 69.89; H, 3.91; N, 6.79; found: C, 69.93; H, 4.01; N, 6.88 %.

2 Experimental details

The hydrogen atoms were located in the difference Fourier map and refined with idealized geometry using a riding model. The O–H bond distance was set at 0.82 Å with free rotation about the C–O bond and displacement parameter 1.5 times Uiso(O). The C–H distances were set to 0.93 Å and their U(iso) to 1.2 times the Uiso(C). Crystal data, data collection and structure refinement details are summarized in Table 1.

3 Comment

Thiazoles display ample biological activity, and many natural products contain such ring systems [5], [6], [7]. Coumarin is a naturally occurring heterocycle, and has various applications [8, 9]. The design, synthesis, and structure elucidation of heterocycles containing thiazole and coumarin moieties is therefore of general interest. The X-ray crystal structures of other related heterocycles have been reported [10], [11], [12].

The crystal structure of C24H16N2O3S is triclinic, with an asymmetric unit consisting of one molecule (Figure 1) which comprises five planar groups, namely: aniline (A: C1–C6, N1), thiazole (B: C7–C9, N2, S1), benzopyranone (C: C10–C18, O1, O2) and phenol (D: C19–C24, O1). The planes through neighbouring groups in the molecules are twisted in relation to each other, with angles A/B = 63.88(7)°, B/C = 54.59(6)°, C/D = 82.09(5)°, B/D = 86.91(7)°.

In the crystal structure, two O–H⋯N hydrogen bonds (O3⋯N1 = 2.733(2) Å, O3–H3A⋯N1 = 161.5°) link pairs of molecules related by inversion symmetry, with the aniline group accepting a contact from the phenol group. These molecular pairs are also involved in π⋯π contacts between neighbouring like groups, specifically symmetry-related benzopyranone pairs and thiazole pairs. The centroid-to-centroid distances are 4.069 Å for the benzopyranone groups and 3.734 Å for the thiazole groups.

Corresponding author: Gamal A. El-Hiti, Cornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, P. O. Box 10219, Riyadh 11433, Saudi Arabia, E-mail:

Funding source: Scientific Research, King Saud University

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

  2. Research funding: We thank the National Research Centre, Cairo, Egypt, and Cardiff University, Cardiff, UK, for their support. G. A. El-Hiti extends his appreciation to the Deanship of Scientific Research, King Saud University, for funding through the Vice Deanship of Scientific Research Chairs, Research Chair of Cornea.

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

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Received: 2023-11-19
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.

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https://doi.org/10.1515/ncrs-2023-0504
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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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