Home The crystal structure of (E)-7-chloro-1-cyclopropyl-6-fluoro-3-((2-hydroxybenzylidene)amino)quinolin-4(1H)-one, C19H14ClFN2O2
Article Open Access

The crystal structure of (E)-7-chloro-1-cyclopropyl-6-fluoro-3-((2-hydroxybenzylidene)amino)quinolin-4(1H)-one, C19H14ClFN2O2

  • Iman M. Ibrahim , Kamrul Hasan ORCID logo , Urmila Ravi , Raed A. Al-Qawasmeh ORCID logo and Monther A. Khanfar ORCID logo EMAIL logo
Published/Copyright: April 18, 2025
Download Article (PDF)
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 3

Abstract

C19H14ClFN2O2, triclinic, P 1 ‾ (no. 2), a = 8.9893(3) Å, b = 9.5324(3) Å, c = 10.1917(4) Å, α = 95.1780(10)°, β = 96.5320(1)°, γ = 116.3930(10)°, V = 767.42(5) Å3, Z = 2, R gt (F) = 0.0355, wR ref (F2) = 0.0966, T = 100(2) K.

CCDC no.: 2440467

The molecular structure is shown in the figure. Table 1 contains crystallographic data. The list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

Table 1:

Data collection and handling.

Crystal: Yellow block
Size: 0.23 × 0.22 × 0.09 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.28 mm−1
Diffractometer, scan mode: Bruker Apex2, φ and ω scans
θmax, completeness: 32.0°, 100 %
N(hkl)measured, N(hkl)unique, Rint: 39,310, 5,348, 0.025
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 4,787
N(param)refined: 229
Programs: Bruker, 1 Olex2, 2 SHELX 3 , 4

1 Source of materials

The preparation of the target compound was performed under the Schiff base typical conditions: To a solution of 3-amino-7-chloro-1-cyclopropyl-6-fluoroquinolin-4(1H)-one (0.4 mmol, 1.0 eq.) in EtOH (4 mL) was added salicylaldehyde (0.436, 1.05 eq.) at room temperature. The reaction was stirred at reflux temperature overnight where no more amine was being observed through TLC. The solution was evaporated to dryness and the obtained crude residue was triturated in diethyl ether and pentane. The target compound was produced in 89 % yield. Crystals were obtained through recrystallization from methanol. The structure of the compound was firstly determined by 1H and 13C NMR and further verified by XRD analyses. 1 H NMR (500 MHz, CDCl3, 298 K): δ 13.45 (s, 1H), 10.23 (s, 1H), 8.22 (d, J = 9.1 Hz, 1H), 8.03 (d, J = 5.9 Hz, 1H), 8.00 (s, 1H), 7.41 (dd, J = 7.6, 1.5 Hz, 1H), 7.32 (ddd, J = 8.8, 7.4, 1.6 Hz, 1H), 6.95 (d, J = 8.2 Hz, 1H), 6.92 (td, J = 7.5, 1.0 Hz, 1H), 3.56–3.43 (m, 1H), 1.39 (q, J = 6.8 Hz, 2H), 1.17 (q, J = 6.7 Hz, 2H). 13 C NMR (125 MHz, CDCl3, 298 K); δ 172.5, 165.3, 161.1, 155.3 (d, JC–F = 249.6 Hz), 142.3, 136.3, 132.7, 132.5, 127.8 (d, JC–F = 5.9 Hz), 126.9 (d, JC–F = 20.5 Hz), 126.2, 120.2, 119.3, 118.7, 117.0, 113.3 (d, JC–F = 22.7 Hz), 34.6, 8.6.

2 Experimental details

All chemicals and solvent were used as purchased without further purification. The starting material 3-amino-7-chloro-1-cyclopropyl-6-fluoroquinolin-4(1H)-one was prepared as described earlier 1 and used directly without crystallization. NMR spectra were recorded with a Bruker Avance III 500 spectrometer. All NMR spectra were reported in parts per million (ppm, δ) relative to tetramethylsilane for 1H and 13C NMR spectra, with the residual solvent proton and carbon resonances were used as internal standards. Coupling constants (J) were reported in Hertz (Hz), and integrations were reported as number of protons. The following abbreviations were used to describe peak patterns: s = singlet, d = doublet, m = multiplet, bs = broad singlet. All H atoms that were bonded to C atoms were refined as riding, with C–H distances of 0.93 Å (for aromatic rings).

3 Discussion

The fluoroquinolone scaffolds are among the most promising chemical agents to fight the bacterial infections world wide. 5 , 6 Structural modification of this scaffold is still an expanding area to generate new entities, which can be used to treat bacterial and fungal strains and mainly to overcome the bacterial resistance. 7 Current trends in this area are based on structural modifications of all position available while keeping the fluorine atom and the carboxylic acid moiety untouched at position 6 and 7, respectively. 5 , 6 , 7 Few approaches tackle the carboxylic acid replacements with heterocyclic rings and their derivatives. 8 In a continuation of our contribution on the fluoroquinolone to produce biologically active agents to combat bacterial infections as well as cancer, 9 , 10 , 11 we envision the introduction of the Schiff base components for their recognized activities. 12 , 13 In this regard the carboxylic acid moiety at position three in the compound 1-cyclopropyl-7-chloro-7-fluoro-quinolone-3-carboxylic acid is converted to nitro and thereafter reduced to get the 3-amine derivative, which herein reacts with salicylaldehyde to produce the desired compound. Eventually, the target compound has been isolated in high percentage yield and recrystallized into triclinic crystal system. The hydroxyl group in the salicylaldehyde shows a clear H-bonding with the imine nitrogen that forms an E isomer, which encouraged us to synthesize the target compound that features the salicylaldehyde and the fluoroquinolone moieties. The amine at position three of the quinolone compounds has been produced via successive decarboxylation-nitration and thereafter reduction to produce an amino group at that position as described in Ref. 14].

In the C19H14ClFN2O2 molecules all bond lengths are in normal ranges. The normal plane of the phenyl ring is almost coplanar with the normal plane of benzoquinolone ring with an angle of 4.46(3)°. This can be attributed to the strong intramolecular hydrogen bonding between H1⋯N1 with distance = 1.795(19) Å and weaker hydrogen bonding between H7⋯O2 with distance = 2.2234(7) Å. These interactions are accompanied by elongation of the O1–H1 to be 1.299(18) Å.

The crystal is stabilized by intramolecular interactions with halogen atom with the following distances: F⋯H (F1⋯H5, +x, −1 + y, 1 + z) = 2.4601(7) Å and Cl⋯H interactions (Cl1⋯H15b, 2 − x, 1 − y, 2 − z) = 2.9534(2) Å. These interactions build up a two-dimensional arrangement of the molecules. These layers are connected to each other by O⋯H hydrogen bonding between O1⋯H14A (−1x, −1 + y, +z) with distance equal 2.4792(7) Å.

Corresponding author: Monther A. Khanfar, Department of Chemistry, Pure and Applied Chemistry Group, College of Sciences, University of Sharjah, Sharjah-27272, UAE; and Department of Chemistry, The University of Jordan, Amman 11942, Jordan, E-mail:

Funding source: University of Sharjah, Sharjah, United Arab Emirates

Award Identifier / Grant number: competitive grant number 23021440137

Acknowledgments

Authors wish to thank the Research Institute of Science and Engineering (RISE), University of Sharjah, Sharjah, United Arab Emirates, competitive grant number 23021440137. Part of this work has been carried out during sabbatical leave granted to MAK from the University of Jordan during the academic year 2021–2022.

References

1. Bruker. APEX4, SAINT and SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2021.Search in Google Scholar

2. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: A Complete Structure Solution, Refinement and Analysis Program. J. Appl. Cryst. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

3. Sheldrick, G. M. SHELXT – Integrated Space-Group and Crystal-Structure Determination. Acta Cryst. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Search in Google Scholar

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

5. Nowakowska, J.; Radomska, D.; Czarnomysy, R.; Marciniec, K. Recent Development of Fluoroquinolone Derivatives as Anticancer Agents. Molecules 2024, 29, 3538; https://doi.org/10.3390/molecules29153538.Search in Google Scholar PubMed PubMed Central

6. Suaifan, G. A.; Mohammed, A. A. M.; Alkhawaja, B. A. Fluoroquinolones’ Biological Activities against Laboratory Microbes and Cancer Cell Lines. Molecules 2024, 27, 1658; https://doi.org/10.3390/molecules27051658.Search in Google Scholar PubMed PubMed Central

7. Mohammed, H. H.; Abuo-Rahma, G. E.-D. A.; Abbas, S.; Abdelhafez, E.-S. M. Current Trends and Future Directions of Fluoroquinolones. Curr. Med. Chem. 2019, 26, 3132–3149; https://doi.org/10.2174/0929867325666180214122944.Search in Google Scholar PubMed

8. Hryhoriv, H.; Kovalenko, S. M.; Georgiyants, M.; Sidorenko, L.; Georgiyants, V. A Comprehensive Review on Chemical Synthesis and Chemotherapeutic Potential of 3-Heteroaryl Fluoroquinolone Hybrids. Antibiotics 2023, 12, 625; https://doi.org/10.3390/antibiotics12030625.Search in Google Scholar PubMed PubMed Central

9. Al-Qawasmeh, R. A.; Zahra, J. A.; Zani, F.; Vicini, P.; Boese, R.; El-Abadelah, M. M. Synthesis and Antibacterial Activity of 9-cyclopropyl-4-fluoro-6-oxo-6, 9-dihydro-[1, 2, 5] thiadiazolo [3, 4-h] quinoline-7-Carboxylic Acid and its Ethyl Ester. Arkivoc: Online J. Org. Chem. 2009, 12, 322–336; https://doi.org/10.3998/ark.5550190.0010.c28.Search in Google Scholar

10. Al-Qawasmeh, R. A.; Huthail, B. B.; Sinnokrot, M. O.; Semreen, M. H.; Odeh, R. A.; Abu-Zarga, M. H.; Tarazi, H.; Yousef, I. A.; Al-Tel, T. H. Design, Synthesis and Qualitative Structure Activity Relationship Evaluations of Quinoline-Based Bisarylimidazoles as Antibacterial Motifs. Med. Chem. 2016, 12l, 563–573; https://doi.org/10.2174/1573406412666160518142441.Search in Google Scholar PubMed

11. Al-Qawasmeh, R. A.; Abadleh, M. M.; Zahra, J. A.; El-Abadelah, M. M.; Albashiti, R.; Zani, F.; Incerti, M.; Vicini, P. Design Synthesis and Antibacterial Activity Studies of New Thiadiazoloquinolone Compounds. J. Enzyme Inhib. Med. Chem. 2014, 29, 777–785; https://doi.org/10.3109/14756366.2013.855925.Search in Google Scholar PubMed

12. Younus, H. A.; Saleem, F.; Hameed, A.; Al-Rashida, M.; Al-Qawasmeh, R. A.; El-Naggar, M.; Khan, K. M.; Saeed, M. Part-II: An Update of Schiff Bases Synthesis and Applications in Medicinal Chemistry-A Patent Review (2016–2023). Expert Opin. Ther. Pat. 2023, 33, 841–864; https://doi.org/10.1080/13543776.2023.2297729.Search in Google Scholar PubMed

13. Tomisic, Z. B.; Kujundzic, N.; Krajacic, M. B.; Visnjevac, A.; Kojic-Prodic, B. J. Mol. Struct. 2002, 611, 73; https://doi.org/10.1016/S0022-2860(02)00062-5.Search in Google Scholar

14. Al-Qawasmeh, R. A.; Zahra, J. A.; Khanfar, M. A.; Al-Hiari, Y. M.; El-Abadelah, M. M.; Voelter, W. A Convenient Synthesis of 1-Alkyl-7-chloro-6- fluoro-3-nitro-4-quinolones. Lett. Org. Chem. 2009, 6, 511–514; https://doi.org/10.2174/157017809789124812.Search in Google Scholar
Received: 2025-03-09
Accepted: 2025-04-02
Published Online: 2025-04-18
Published in Print: 2025-06-26

© 2025 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 5,5′-bis(2,4,6-trinitrophenyl)-2,2′-bi(1,3,4-oxadiazole), C16H4N10O14
  4. Crystal structure of catena-poly[(μ3-4,4′-oxydibenzoato- κ5 O,O′: O″,O‴:O‴)-bis(2,4,6-tri(3-pyridine)-1,3,5-triazine-κ1 N)cadmium(II)], C50H32CdN12O5
  5. The crystal structure of 1,4-diazepane-1,4-diium potassium trinitrate, C5H14KN5O9
  6. The crystal structure of benzyl 2,2,5,5-tetramethylthiazolidine-4-carboxylate, C15H21NO2S
  7. Crystal structure of 2-hydroxyethyl-triphenylphosphonium tetracyanidoborate, C24H20BN4OP
  8. The crystal structure of 1-methyl-3-(N-methylnitrous amide–N-methylene) imidazolidine-2,4,5-trione
  9. Crystal structure of N-((3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(2,2,2-trifluoroacetyl)-1H-pyrazol-5-yl)carbamoyl)-2,6-difluorobenzamide, C20H7Cl2F8N5O3S
  10. Crystal structure of 5-(2,2-difluoropropyl)-5-methylbenzo[4,5]imidazo[2,1-a] isoquinolin-6(5H)-one, C20H18F2N2O
  11. The crystal structure of N′,N″-[1,2-bis(4-chlorophenyl)ethane-1,2-diylidene]bis(furan-2- carbohydrazide), C24H16Cl2N4O4
  12. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromoantimony(III), [C25H21BrP]+[SbBr4]−
  13. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromidoindium(III), [C25H21BrP]+[InBr4]−
  14. The crystal structure of 4-carboxy-2-oxobutan-1-aminium chloride, C5H10ClNO3
  15. Crystal structure of (4-(4-chlorophenyl)-1H-pyrrole-3-carbonyl)ferrocene, C21H16ClFeNO
  16. The crystal structure of dichlorido(η6-p-cymene)(triphenylarsine)ruthenium(II), C28H29AsCl2Ru
  17. Crystal structure of (Z)-2-hydroxy-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H16N2O2
  18. The crystal structure of 10-(1-bromoethyl)-14-(bromomethyl)dibenzo[a, c]acridine, C24H17NBr2
  19. Synthesis and crystal structure of 6-methoxy-7-[(4-methoxyphenyl)methoxy]-2H-1-benzopyran-2-one, C18H16O5
  20. Synthesis and crystal structure of ethyl 4-((4-trifluoromethylbenzyl)amino)benzo, C17H16F3NO2
  21. The crystal structure of (Z)-2-(tert-butyl)-6-(7-(tert-butyl)-5-methylbenzo[d][1,3]oxathiol-2-ylidene)-4-methylcyclohexa-2,4-dien-1-one, C23H28O2S
  22. The crystal structure of (R)-2-aminobutanamide hydrochloride, C4H11ClN2O
  23. Crystal structure of bromido[hydridotris(3-tert-butyl-5-isopropylpyrazolyl)borato-κ3 N,N′,N″]copper(II), C30H52BBrCuN6
  24. Crystal structure of chlorido{hydridotris[3-mesityl-5-methyl-1H-pyrazol-1-yl-κN3]borato}-copper(II) dichloromethane monosolvate
  25. Crystal structure of 4-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]pyridine, C14H19N3
  26. Crystal structure of ((4-(4-bromophenyl)-1H-pyrrol-3-yl)methyl)ferrocene, C21H16BrFeNO
  27. Crystal structure of [(4-chlorobenzyl)triphenylphosphonium] dichloridocopper(I), {[C25H21ClP]+[CuCl2]−}n
  28. The crystal structure of {Cu(2,9-diisopropyl-4,7-diphenyl-1,10-phenanthroline)[4,5-bis(diphenylphosphino)-9,9-dimethylxanthene]}+ PF6−·1.5(EtOAC)
  29. Crystal structure of 3,5-bis(t-butyl)-1H-pyrazol-4-amine, C11H21N3
  30. Crystal structure of [(2,4-dichlorobenzyl)triphenylphosphonium] trichloridocopper(II), [C25H20Cl2P]+[CuCl3]−
  31. The crystal structure of dipotassium sulfide, K2S
  32. Crystal structure of (4-(4-methoxyphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C22H19FeNO2
  33. Crystal structure of (E)-6-(4-methylpiperazin-1-yl)-2-(4-(trifluoromethyl)benzylidene)-3, 4-dihydronaphthalen-1(2H)-one, C23H23F3N2O
  34. Crystal structure of (E)-6-morpholino-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H20F3NO2
  35. Crystal structure of Ce9Ir37Ge25
  36. The crystal structure of ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate, C14H11N3O4S
  37. Crystal structure of (4-(4-isopropylphenyl)-1H-pyrrol-3-yl)(ferrocenyl)methanone, C24H23FeNO
  38. Crystal structure of bis(methylammonium) tetrathiotungstate(VI), (CH3NH3)2[WS4]
  39. Crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one, C17H12O2
  40. Crystal structure of 3-[(4-phenylpiperidin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4- oxadiazole-2-thione, C18H19N3OS2
  41. Crystal structure of N-isopropyl-1,8-naphthalimide C15H13NO2
  42. TiNiSi-type EuPdBi
  43. Crystal structure of 1-(p-tolylphenyl)-4-(2-thienoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O2S
  44. The crystal structure of 3-(3-carboxypropyl)-2-nitro-1H-pyrrole 1-oxide, C7H9N3O5
  45. The crystal structure of tetraaqua-bis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k2O:N)-tetrakis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k1N)trizinc(II) hexahydrate C36H52N18O32Zn3
  46. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-hydroxy-3,5-dimethoxybenzoate monohydrate, C25H30FN3O9
  47. Crystal structure of bis(DL-1-carboxy-2-(1H-indol-3-yl)ethan-1-aminium) oxalate — acetic acid (1/2)
  48. Crystal structure of methyl (E)-4-((4-methylphenyl)sulfonamido)but-2-enoate, C12H15NO4S
  49. The crystal structure of actarit, C10H11NO3
  50. The crystal structure of bicyclol, C19H18O9
  51. The crystal structure of topiroxostat, C13H8N6
  52. Crystal structure of 2,2-dichloro-N-methyl-N-(4-p-tolylthiazol-2-yl)acetamide, C13H12Cl2N2OS
  53. Crystal structure of 4-(trifluoromethyl)-7-coumarinyl trifluoromethanesulfonate C11H4F6O5S
  54. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6)-((Z)-N,N′-bis(2-(dimethylamino)phenyl)carbamimidato-κ1N)potassium(I)
  55. Crystal structure of (Z)-2-(5-((4-(dimethylamino)naphthalen-1-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid, C18H16N2O3S2
  56. Crystal structure of (4-fluorobenzyl)triphenylphosphonium bromide, C25H21BrFP
  57. The crystal structure of dichlorido-[6-(pyridin-2-yl)phenanthridine-κ2N, N′]zinc(II)-chloroform (1/1), C19H13N2ZnCl5
  58. Crystal structure of (E)-(3-(2,4-dichlorophenyl)acryloyl)ferrocene, C19H14Cl2FeO
  59. The crystal structure of (E)-7-chloro-1-cyclopropyl-6-fluoro-3-((2-hydroxybenzylidene)amino)quinolin-4(1H)-one, C19H14ClFN2O2
  60. Crystal structure of 2-bromo-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13BrFNO4S2
  61. Crystal structure of 2-chloro-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13ClFNO4S2
  62. Crystal structure of 5-(2,2-difluoropropyl)-5-methyl-6-oxo-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline-3-carbonitrile, C20H15F2N3O
https://doi.org/10.1515/ncrs-2025-0124
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of 5,5′-bis(2,4,6-trinitrophenyl)-2,2′-bi(1,3,4-oxadiazole), C16H4N10O14
  4. Crystal structure of catena-poly[(μ3-4,4′-oxydibenzoato- κ5 O,O′: O″,O‴:O‴)-bis(2,4,6-tri(3-pyridine)-1,3,5-triazine-κ1 N)cadmium(II)], C50H32CdN12O5
  5. The crystal structure of 1,4-diazepane-1,4-diium potassium trinitrate, C5H14KN5O9
  6. The crystal structure of benzyl 2,2,5,5-tetramethylthiazolidine-4-carboxylate, C15H21NO2S
  7. Crystal structure of 2-hydroxyethyl-triphenylphosphonium tetracyanidoborate, C24H20BN4OP
  8. The crystal structure of 1-methyl-3-(N-methylnitrous amide–N-methylene) imidazolidine-2,4,5-trione
  9. Crystal structure of N-((3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(2,2,2-trifluoroacetyl)-1H-pyrazol-5-yl)carbamoyl)-2,6-difluorobenzamide, C20H7Cl2F8N5O3S
  10. Crystal structure of 5-(2,2-difluoropropyl)-5-methylbenzo[4,5]imidazo[2,1-a] isoquinolin-6(5H)-one, C20H18F2N2O
  11. The crystal structure of N′,N″-[1,2-bis(4-chlorophenyl)ethane-1,2-diylidene]bis(furan-2- carbohydrazide), C24H16Cl2N4O4
  12. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromoantimony(III), [C25H21BrP]+[SbBr4]−
  13. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromidoindium(III), [C25H21BrP]+[InBr4]−
  14. The crystal structure of 4-carboxy-2-oxobutan-1-aminium chloride, C5H10ClNO3
  15. Crystal structure of (4-(4-chlorophenyl)-1H-pyrrole-3-carbonyl)ferrocene, C21H16ClFeNO
  16. The crystal structure of dichlorido(η6-p-cymene)(triphenylarsine)ruthenium(II), C28H29AsCl2Ru
  17. Crystal structure of (Z)-2-hydroxy-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H16N2O2
  18. The crystal structure of 10-(1-bromoethyl)-14-(bromomethyl)dibenzo[a, c]acridine, C24H17NBr2
  19. Synthesis and crystal structure of 6-methoxy-7-[(4-methoxyphenyl)methoxy]-2H-1-benzopyran-2-one, C18H16O5
  20. Synthesis and crystal structure of ethyl 4-((4-trifluoromethylbenzyl)amino)benzo, C17H16F3NO2
  21. The crystal structure of (Z)-2-(tert-butyl)-6-(7-(tert-butyl)-5-methylbenzo[d][1,3]oxathiol-2-ylidene)-4-methylcyclohexa-2,4-dien-1-one, C23H28O2S
  22. The crystal structure of (R)-2-aminobutanamide hydrochloride, C4H11ClN2O
  23. Crystal structure of bromido[hydridotris(3-tert-butyl-5-isopropylpyrazolyl)borato-κ3 N,N′,N″]copper(II), C30H52BBrCuN6
  24. Crystal structure of chlorido{hydridotris[3-mesityl-5-methyl-1H-pyrazol-1-yl-κN3]borato}-copper(II) dichloromethane monosolvate
  25. Crystal structure of 4-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]pyridine, C14H19N3
  26. Crystal structure of ((4-(4-bromophenyl)-1H-pyrrol-3-yl)methyl)ferrocene, C21H16BrFeNO
  27. Crystal structure of [(4-chlorobenzyl)triphenylphosphonium] dichloridocopper(I), {[C25H21ClP]+[CuCl2]−}n
  28. The crystal structure of {Cu(2,9-diisopropyl-4,7-diphenyl-1,10-phenanthroline)[4,5-bis(diphenylphosphino)-9,9-dimethylxanthene]}+ PF6−·1.5(EtOAC)
  29. Crystal structure of 3,5-bis(t-butyl)-1H-pyrazol-4-amine, C11H21N3
  30. Crystal structure of [(2,4-dichlorobenzyl)triphenylphosphonium] trichloridocopper(II), [C25H20Cl2P]+[CuCl3]−
  31. The crystal structure of dipotassium sulfide, K2S
  32. Crystal structure of (4-(4-methoxyphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C22H19FeNO2
  33. Crystal structure of (E)-6-(4-methylpiperazin-1-yl)-2-(4-(trifluoromethyl)benzylidene)-3, 4-dihydronaphthalen-1(2H)-one, C23H23F3N2O
  34. Crystal structure of (E)-6-morpholino-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H20F3NO2
  35. Crystal structure of Ce9Ir37Ge25
  36. The crystal structure of ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate, C14H11N3O4S
  37. Crystal structure of (4-(4-isopropylphenyl)-1H-pyrrol-3-yl)(ferrocenyl)methanone, C24H23FeNO
  38. Crystal structure of bis(methylammonium) tetrathiotungstate(VI), (CH3NH3)2[WS4]
  39. Crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one, C17H12O2
  40. Crystal structure of 3-[(4-phenylpiperidin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4- oxadiazole-2-thione, C18H19N3OS2
  41. Crystal structure of N-isopropyl-1,8-naphthalimide C15H13NO2
  42. TiNiSi-type EuPdBi
  43. Crystal structure of 1-(p-tolylphenyl)-4-(2-thienoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O2S
  44. The crystal structure of 3-(3-carboxypropyl)-2-nitro-1H-pyrrole 1-oxide, C7H9N3O5
  45. The crystal structure of tetraaqua-bis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k2O:N)-tetrakis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k1N)trizinc(II) hexahydrate C36H52N18O32Zn3
  46. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-hydroxy-3,5-dimethoxybenzoate monohydrate, C25H30FN3O9
  47. Crystal structure of bis(DL-1-carboxy-2-(1H-indol-3-yl)ethan-1-aminium) oxalate — acetic acid (1/2)
  48. Crystal structure of methyl (E)-4-((4-methylphenyl)sulfonamido)but-2-enoate, C12H15NO4S
  49. The crystal structure of actarit, C10H11NO3
  50. The crystal structure of bicyclol, C19H18O9
  51. The crystal structure of topiroxostat, C13H8N6
  52. Crystal structure of 2,2-dichloro-N-methyl-N-(4-p-tolylthiazol-2-yl)acetamide, C13H12Cl2N2OS
  53. Crystal structure of 4-(trifluoromethyl)-7-coumarinyl trifluoromethanesulfonate C11H4F6O5S
  54. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6)-((Z)-N,N′-bis(2-(dimethylamino)phenyl)carbamimidato-κ1N)potassium(I)
  55. Crystal structure of (Z)-2-(5-((4-(dimethylamino)naphthalen-1-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid, C18H16N2O3S2
  56. Crystal structure of (4-fluorobenzyl)triphenylphosphonium bromide, C25H21BrFP
  57. The crystal structure of dichlorido-[6-(pyridin-2-yl)phenanthridine-κ2N, N′]zinc(II)-chloroform (1/1), C19H13N2ZnCl5
  58. Crystal structure of (E)-(3-(2,4-dichlorophenyl)acryloyl)ferrocene, C19H14Cl2FeO
  59. The crystal structure of (E)-7-chloro-1-cyclopropyl-6-fluoro-3-((2-hydroxybenzylidene)amino)quinolin-4(1H)-one, C19H14ClFN2O2
  60. Crystal structure of 2-bromo-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13BrFNO4S2
  61. Crystal structure of 2-chloro-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13ClFNO4S2
  62. Crystal structure of 5-(2,2-difluoropropyl)-5-methyl-6-oxo-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline-3-carbonitrile, C20H15F2N3O
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 19.10.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2025-0124/html?lang=en
Scroll to top button