Startseite Naturwissenschaften Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
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Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O

  • Yu Chen , Ji-Peng Wang , Mei-Dan Wang , Wen-Xiao Yu , Yao-Tian Cui , Hao-Xue Gao , Gui-Ge Hou ORCID logo und Yan Ren EMAIL logo
Veröffentlicht/Copyright: 29. Oktober 2024

Abstract

C20H15FN2O, triclinic, P 1 (no. 2), a = 8.0724(1) Å, b = 9.6473(1) Å, c = 9.6635(1) Å, α = 80.903(1)°, β = 82.325(1)°, γ = 84.147(1)°, V = 733.922(14) Å3, Z = 2, Rgt (F) = 0.0366, wRref (F 2) = 0.0934, T = 293 K.

CCDC no.: 2333002

The crystal structure is shown in the Figure. Displacement ellipsoids are drawn at the 30 % probability level. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Yellow block
Size: 0.15 × 0.13 × 0.10 mm
Wavelength: Cu Kα radiation (1.54178 Å)
μ: 0.81 mm−1
Diffractometer, scan mode: XtaLAB AFC12 (RINC),
θ max, completeness: 71.9°, 99 %
N(hkl)measured, N(hkl)unique, R int: 6,303, 2,770, 0.014
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2,687
N(param)refined: 218
Programs: CrysAlisPRO 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
C1 0.82305 (14) 0.64246 (12) −0.13061 (12) 0.0226 (3)
C2 0.77436 (14) 0.73780 (12) −0.02250 (12) 0.0223 (3)
C3 0.90416 (15) 0.83353 (12) −0.00444 (13) 0.0255 (3)
H3A 0.870902 0.874896 0.081287 0.031*
H3B 0.911473 0.909311 −0.083435 0.031*
C4 1.07581 (15) 0.75065 (13) 0.00353 (13) 0.0266 (3)
H4A 1.159296 0.814850 0.007953 0.032*
H4B 1.071606 0.682666 0.089119 0.032*
C5 1.29487 (15) 0.65281 (13) −0.17719 (13) 0.0271 (3)
H5 1.377630 0.682788 −0.133197 0.032*
C6 1.34109 (15) 0.58753 (13) −0.29541 (13) 0.0286 (3)
H6 1.453236 0.573879 −0.331600 0.034*
C7 1.21586 (15) 0.54301 (12) −0.35851 (13) 0.0262 (3)
C8 1.04922 (15) 0.55929 (12) −0.30723 (12) 0.0247 (3)
H8 0.968042 0.526767 −0.351028 0.030*
C9 1.00428 (14) 0.62582 (12) −0.18776 (12) 0.0218 (3)
C10 1.12670 (14) 0.67499 (12) −0.12191 (12) 0.0229 (3)
C11 0.62089 (14) 0.72668 (12) 0.05057 (12) 0.0233 (3)
H11 0.563242 0.655199 0.030039 0.028*
C12 0.52927 (14) 0.80754 (12) 0.15656 (12) 0.0227 (3)
C13 0.39888 (14) 0.74504 (12) 0.24790 (12) 0.0246 (3)
H13 0.374321 0.655116 0.238504 0.030*
C14 0.30593 (14) 0.81330 (13) 0.35142 (13) 0.0256 (3)
H14 0.220059 0.769395 0.410675 0.031*
C15 0.34086 (14) 0.94791 (12) 0.36703 (12) 0.0219 (3)
C16 0.46513 (15) 1.01424 (12) 0.27461 (13) 0.0259 (3)
H16 0.486813 1.105295 0.282638 0.031*
C17 0.55700 (15) 0.94529 (13) 0.17041 (13) 0.0263 (3)
H17 0.638856 0.991496 0.108326 0.032*
C18 0.15526 (14) 0.95435 (13) 0.59372 (12) 0.0250 (3)
H18 0.140833 0.858480 0.611856 0.030*
C19 0.23889 (15) 1.15810 (13) 0.48889 (13) 0.0281 (3)
H19 0.289392 1.229127 0.425915 0.034*
C20 0.14064 (16) 1.17197 (13) 0.61159 (13) 0.0305 (3)
H20 0.112239 1.256746 0.646644 0.037*
F1 1.26047 (9) 0.48216 (8) −0.47745 (8) 0.0357 (2)
N1 0.24878 (12) 1.01667 (10) 0.47639 (10) 0.0229 (2)
N2 0.08820 (13) 1.04393 (11) 0.67778 (11) 0.0295 (3)
O1 0.72062 (10) 0.58009 (10) −0.17490 (9) 0.0320 (2)

1 Source of material

Synthesis method based on literature in Ref. 4: in a 250 mL spherical backside flask, imidazole (10.88 g, 0.16 mol) and potassium carbonate (27.64 g, 0.2 mol) were reacted with N,N-dimethylformamide (10.0 mL) at 353 K for 4 h. The p-fluorobenzaldehyde (2.48 g, 0.02 mol) is added and the temperature is raised to 393 K for reflux. Thin-Layer Chromatography (TLC, dichloromethane:methyl alcohol = 15:1, v:v) was used for detection. After the response, the yellow intermediate was purified by extraction, vacuum distillation and silica gel column (dichloromethane:methyl alcohol = 30:1, v:v). Using 25 % sodium hydroxide (2.0 mL) as catalyst, the intermediate (1.70 g, 10.00 mmol) and 7-fluoro-3,4-dihydronaphthhalen-1(2H)-one (2.30 g, 10.00 mmol) were dissolved in methanol (5.0 mL) and stirred at room temperature for 1 h. Filtered and the filter cake dissolved in methylene chloride, the crude product was obtained by vacuum distillation and recrystallized at 293 K to obtain yellow crystals (dichloromethane:methyl alcohol = 1:1, v:v).

2 Experimental details

The H atoms were placed in idealized positions and treated as riding on their parent atoms, with d (C–H) = 0.97 Å (methylene), U iso(H) = 1.2U eq(C), and d(C–H) = 0.93 Å (aromatic), U iso(H) = 1.2U eq(C).

3 Comment

It has been established that 3,4-dihydronaphthalene-1(2H)-one derivatives act as a,b-unsaturated ketones having proper anti-tumor and anti-inflammatory things to do. 4 , 5 It frequently inhibits the activation of NF-κB transcription factors in vivo to exert therapeutic effects. 6 In order to similarly discover molecules with higher therapeutic effects, we selected to introduce an imidazole ring at the C15 position, it can no longer solely enhance the water solubility of molecules via intramolecular hydrogen bonding, and it additionally has incredible contributions in antibacterial and anti-inflammatory aspects. 7 In this study, p-fluorobenzaldehyde and imidazole reacted to acquire 4-(1H-imidazol-1-yl)benzaldehyde intermediate. Then, the intermediate reacts with 7-fluoro-3,4-dihydronaphthalen-1(2H)-one to obtain the title compound through the Claisen–Schmidt reaction.

Single-crystal structure analysis reveals that there is only a molecule in the asymmetric unit of the title crystal structure (cf. the Figure). Bond lengths and angles are all in the expected ranges. 8 , 9 , 10 Fluorine atoms with electron withdrawing properties replace the 7 position of 3,4-dihydronaphthalene-1(2H)-one, and the introduction of fluorine can decorate organic undertaking and enhance metabolism. 11 In the C(2) position, a,b-unsaturated ketone was obtained through the Claisen–Schmidt reaction. 8 , 9 , 12 The torsion angle of O(1)=C(1)–C(2)=C(11) is about 15.96(17)°. The bond lengths of O(1)=C(1) and C(2)=C(11) are 1.2274(14) Å and 1.3470(16) Å, respectively. In the C(15) position, there’s an imidazole group substitution. Nitrogen atoms on imidazole groups have lone pair electrons, which are easy to act as hydrogen bond receptors and form hydrogen bond or electrostatic interaction with bioactive molecules. 7 The dihedral angle between 3,4-dihydronaphthalene-1(2H)-one and phenyl group is about 49.2°. The dihedral angle between the phenyl group and the imidazole group is about 16.8°.


Corresponding author: Yan Ren, School of Pharmacy, Binzhou Medical University, Yantai, 264003, P.R. China, E-mail:

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

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

  3. Research funding: Shandong Provincial Natural Science Foundation (Nos. ZR2022MH159 and ZR2023MH190) and Shandong Province Science and Technology-based Small and Medium-sized Enterprises Innovation Capacity Enhancement Project (No. 2023TSGC0870).

References

1. Rigaku, O. D. CrysAlisPRO; Rigaku Oxford Diffraction Ltd: Yarnton, Oxfordshire, England, 2017.Suche in Google Scholar

2. Sheldrick, G. M. A Short History of SHELX. Acta Crystallogr. 2008, A64, 112–122. https://doi.org/10.1107/s0108767307043930.Suche in Google Scholar PubMed

3. Sheldrick, G. M. Crystal Structure Refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8. https://doi.org/10.1107/s2053229614024218.Suche in Google Scholar

4. Li, W. X.; Yu, L.; Chi, J. B.; Wang, J. P.; Liu, Y. J.; Wang, C. H.; Zhang, M.; Hou, G. G. Discovery of Anti-Inflammatory Agents from 3, 4-Dihydronaphthalene-1(2h)-One Derivatives by Inhibiting NLRP3 Inflammasome Activation. Eur. J. Med. Chem. 2024, 268, 116284. https://doi.org/10.1016/j.ejmech.2024.116284.Suche in Google Scholar PubMed

5. Zhang, X. F.; Luan, M. Z.; Yan, W. B.; Zhao, F. L.; Hou, Y.; Hou, G. G.; Meng, Q. G. Anti-Neuroinflammatory Effects of Novel 5, 6-Dihydrobenzo [h]quinazolin-2-Amine Derivatives in Lipopolysaccharide-Stimulated BV2 Microglial Cells. Eur. J. Med. Chem. 2022, 235, 114322. https://doi.org/10.1016/j.ejmech.2022.114322.Suche in Google Scholar PubMed

6. Luan, M. Z.; Zhang, X. F.; Yang, Y.; Meng, Q. G.; Hou, G. G. Anti-Inflammatory Activity of Fluorine-Substituted Benzo[h]quinazoline-2-Amine Derivatives as NF-Κb Inhibitors. Bioorg. Chem. 2023, 132, 106360. https://doi.org/10.1016/j.bioorg.2023.106360.Suche in Google Scholar PubMed

7. Chopra, P. N.; Sahu, J. K. Biological Significance of Imidazole-Based Analogues in New Drug Development. Curr. Drug Discov. Technol. 2020, 17, 574–584. https://doi.org/10.2174/1570163816666190320123340.Suche in Google Scholar PubMed

8. Li, Y. L.; Meng, Q. G.; Hou, G. G.; Geng, Z. K. Crystal Structure of 2-((2-Fluoro-4-(Trifluoromethyl)Phenyl)(Hydroxy)Methyl)-7-Methoxy-3,4-Dihydronaphthalen-1((2h))-One, C19H16F4O3. Z. Kristallogr. N. Cryst. Struct. 2023, 238, 1157–1159. https://doi.org/10.1515/ncrs-2023-0373.Suche in Google Scholar

9. Yu, L.; Wang, J.-P.; Wang, M.-D.; Yu, W.-X.; Cui, Y.-T.; Gao, H.-X.; Liu, Y.-J.; Hou, G.-G. Crystal Structure of (E)-6-(4-Ethylpiperazin-1-yl)-2-(3-Fluorobenzylidene)-3,4-Dihydronaphthalen-1(E)-One, C23H25FN2O. Z. Kristallogr. N. Cryst. Struct. 2024, 239, 515–517. https://doi.org/10.1515/ncrs-2024-0066.Suche in Google Scholar

10. Baddeley, T. C.; Gomes, L. R.; Low, J. N.; Turner, A. B.; Wardell, J. L.; Watson, G. J. R. Structural Studies of (E)-2-(Benzylidene)-1-Tetralone Derivatives: Crystal Structures and Hirshfeld Surface Analysis. Z. Kristallogr. N. Cryst. Struct. 2017, 232, 697–718. https://doi.org/10.1515/zkri-2017-2048.Suche in Google Scholar

11. Shah, P.; Westwell, A. D. The Role of Fluorine in Medicinal Chemistry. J. Enzyme Inhib. Med. Chem. 2007, 22, 527–540. https://doi.org/10.1080/14756360701425014.Suche in Google Scholar PubMed

12. Luo, H. L.; Li, W. X.; Bai, X. Y.; Meng, Q. G.; Hou, Y. Crystal Structure of (E)-7-Fluoro-2-(4-Morpholinobenzylidene)-3,4-Dihydronaphthalen-1(2H)-One, C21H20FNO2. Z. Kristallogr. N. Cryst. Struct. 2023, 238, 495–497. https://doi.org/10.1515/ncrs-2023-0053.Suche in Google Scholar

Received: 2024-07-10
Accepted: 2024-08-22
Published Online: 2024-10-29
Published in Print: 2025-02-25

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

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
  4. Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
  5. Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
  6. Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
  7. Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
  8. Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
  9. The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
  10. The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
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  12. The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
  13. Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  14. The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
  15. The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
  16. Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
  17. The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
  18. Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
  19. The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
  20. The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
  21. Crystal structure of (−)-flavesine H, C15H22N2O2
  22. Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
  23. Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
  24. The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
  25. The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
  26. Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
  27. The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
  28. The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
  29. The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
  30. Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
  31. Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
  32. Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
  33. Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
  34. Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
  35. Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
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