Startseite Naturwissenschaften Crystal structure of 4-((cyclohexylsulfonyl)methyl)-1,2,3,4-tetrahydrobenzo [4,5]imidazo[1,2-a]pyridine, C18H24N2O2S
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Crystal structure of 4-((cyclohexylsulfonyl)methyl)-1,2,3,4-tetrahydrobenzo [4,5]imidazo[1,2-a]pyridine, C18H24N2O2S

  • Jiajie Li ORCID logo , Yuanyuan Wang , Sihong Sang EMAIL logo und Liyan Zhang EMAIL logo
Veröffentlicht/Copyright: 17. September 2025

Abstract

C18H24N2O2S, monoclinic, P21/c (no. 14), a = 27.3975(7) Å, b = 6.16564(14) Å, c = 9.9182(2) Å, β = 99.202(2)°, V = 1653.86(7) Å3, Z = 4, R gt (F) = 0.0586, wR ref (F2) = 0.1544, T = 100(1) K.

CCDC no.: 2484880

The molecular structure is shown in the figure Table 1 contains the crystallographic data and 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: Clear light colourless block
Size: 0.16 × 0.13 × 0.12 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 1.83 mm−1
Diffractometer, scan mode: Bruker Apex-II, φ and ω scans
θmax, completeness: 74.6°, 99 %
N(hkl)measured, N(hkl)unique, Rint: 12558, 3262, 0.032
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 3222
N(param)refined: 209
Programs: Olex2, 1 Bruker, 2 SHELX, 3 Diamond 4

1 Source of material

To an oven-dried Schlenk tube equipped with a magnetic stir bar were sequentially added 1-(pent-4-en-1-yl)-1H-benzo[d]imidazole (40.43 mg, 0.2 mmol), diethyl 4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (160.00 mg, 0.4 mmol), DABSO (96.12 mg, 0.4 mmol), ammonium persulfate (45.64 mg, 0.2 mmol), Eosin Y (2 mol %) and DCM (2.0 mL). After being degassed and refilled with nitrogen three times, the tube was sealed, and the reaction mixture was stirred under 20 W blue LED irradiation at room temperature for 24 h. After that, the solvent was removed by vacuum evaporation, and the crude residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexanes (1:10 to 1:8) to give the desired product.

2 Experimental details

The carbon-bound hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

3 Comment

Benzimidazoles and their derivatives exhibit significant biological activity, positioning them as potential anticancer agents. Benzimidazole is a bicyclic compound characterized by an imidazole ring containing two non-adjacent nitrogen atoms thickened with a benzene ring. The backbone structure possesses diverse pharmacological properties including antiviral, antifungal, antioxidant, anticancer and anthelmintic activities. Incorporation of the core structure of benzimidazoles into drug development continues to play a key role in contemporary therapeutic research, providing versatile and effective therapeutic avenues for a wide range of diseases. 5 , 6 , 7 , 8

The title compound contains a sulfonyl group. 9 , 10 According to the title structure, the bond lengths and angles obtained are within normal ranges. The sulfonyl groups were determined at the distance of 1.447 (2) Å (S1–O1), 1.447 (2) Å (S1–O1), 1.789 (3) Å (S1–C12), 1.800 (3) Å (S2–C13). Geometric parameters are all in the expected range.


Corresponding authors: Sihong Sang and Liyan Zhang, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, P.R. China, E-mail: (S. Sang), (L. Zhang)

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

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

  3. Research funding: Guizhou Provincial Basic Research Program (Natural Science) QKHJC–ZK[2021] general 086.

References

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Received: 2025-07-11
Accepted: 2025-09-04
Published Online: 2025-09-17
Published in Print: 2025-12-17

© 2025 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. The crystal structure of (1Z, 2Z)-3-phenyl-2-propenal 2-(4-bromo-2-fluorophenyl)hydrazone, C15H12BrFN2
  4. Refinement of crystal structure of 2-(2,3-dihydro-3-oxo-1 H -inden-1-ylidene)-1 H -indene-1,3(2 H )-dione C18H10O3
  5. The crystal structure of 3-(1-fluoro-2-(naphthalen-2-yl)-2-oxoethyl)-2-methoxy-3,4-dihydroisoquinolin-1(2H)-one, C22H18FNO3
  6. Crystal structure of the dinuclear copper(II) complex bis(μ2-2,2′ -{[1,3-phenylenebis-(methylene)]bis(oxy)}dibenzoaot-κ4O,O′:O′′,O′′′)-bis(dimethylformamide-κ1O)dicopper(II), C50H44Cu2N2O14
  7. Crystal structure of poly[triaqua-(μ9-biphenyl-3,3′,5,5′-tetracarboxylic-κ8 O,O:O,O′: O,O″:O,O‴)samarium(III)sodium(I)], C16H12NaSmO11
  8. The crystal structure of 5-benzyl-1-(4-fluorobenzyl)-4-((4-fluorobenzyl)oxy)-1,5-dihydro-2H-pyrrol-2-one, C25H21F2NO2
  9. The crystal structure of diammonium 2,5-dihydroxyterephthalate, C8H12N2O6
  10. Crystal structure of (E)-4-(4-(1H-1,2,4-triazol-1-yl)benzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C21H19N3O4
  11. Crystal structure of poly[oktakis(μ2-oxido-κ2O:O)-tetrakis(oxido-κ1O)-bis(μ2-1,1′-[1,4-phenylenebis(methylene)]di(1H-imidazole-κ2N:N′))-tetravanadium(V)-dizinc(II)] monohydrate, C28H30Zn2N8O13V4
  12. Crystal structure of acotiamide hydrochloride dimethylacetamide solvate (1/1), C25H40ClN5O6S
  13. Crystal structure of catena-poly[monoaqua (u2-(3-(3,5-dicarboxyphenyl)pyridine-2,6-dicarboxylic-k4O:O′:O″:N)zinc(II))] monohydrate, C15H11NO10Zn
  14. Crystal structure of dichlorido{2,6-bis(3,5-diisopropyl-N-pyrazolyl)pyridine}zinc(II), C23H33Cl2N5Zn
  15. Crystal structure of nitrato-κ2O,O′-[hydridotris(3,5-diethylpyrazol-1-yl)borato-κ3N,N′,N″]copper(II), C21H34BCuN7O3
  16. Crystal structure of 2,7-bis(3,5-diethyl-1H-pyrazol-4-yl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, C28H26N6O4
  17. Crystal structure of 2-(4-chlorophenyl)benzothiazole, C13H8ClNS
  18. Synthesis and crystal structure (3R,4′S)-4′-(3,5-dibromophenyl)-1′-methyl-2H-dispiro [benzofuran-3,3′-pyrrolidine-2′,2″-indene]-1″,2,3″-trione, C26H17Br2NO4
  19. Crystal structure of bis(((3a,7a-dihydro-1H-benzo[d][1,2,3]triazol-1-yl)methyl) triphenylphosphonium) tetrachloridomanganate(II), C50H42Cl4MnN6P2
  20. The crystal structure of 4,9-bis(4-chlorophenyl)-1,6-bis(2-cyanobenzyl)-2,4a,5,6,7,7a-hexahydro-1H-2,7,5-(epiprop[2]ene[1,1,3]triyl)pyrrolo[3,4-b]pyridine-3,10-dicarbonitrile, C40H26Cl2N6
  21. The crystal structure of poly((μ2-3-(3-nitro-4-carboxylphenyl)benzoate-κ3O, O′:O″)-μ2-1,4-bis(1-imidazolyl)benzene-κ2N:N′-cadmium(II)), C26H17N5O6Cd
  22. The crystal structure of 6-hydroxy-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione monohydrate, C7H6N2O4
  23. Crystal structure of 4-((cyclohexylsulfonyl)methyl)-1,2,3,4-tetrahydrobenzo [4,5]imidazo[1,2-a]pyridine, C18H24N2O2S
  24. Crystal structure of 4,7-diphenyl-1,10-phenanthroline-κ2N,N′)-bis(2,4-di(fluorine)-1-phenylpyridine-κ2C,N)-iridium(III) hexafluorophosphate–dichloromethane (1/1), C47H30Cl2F10IrN4P
  25. Crystal structure of (4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid, C19H15BN2O2
  26. The crystal structure of (E)-(2-((pyridin-2-ylmethylene)amino)phenyl)arsonic acid, C12H11AsN2O3
  27. The crystal structure of N(benzyl(phenyl)carbomothioyl)benzamide, C21H18N2OS
  28. The crystal structure of bis(2-picolinium) hexachlorostannate dichloromethane monosolvate, C13H18Cl8N2Sn
  29. Crystal structure of poly[tetraaqua-bis(μ4-3–1-(carboxylatomethyl)-1H-1,2,4-triazole-3-carboxylato)-κ4O:O′,O″,N)zinc(II)], C5H7N3O6Zn
  30. The crystal structure of the co-crystal isonicotinamide – 2-(nitrophenyl)methanol (1/1), C6H6N2O·C7H7NO3
  31. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-fluorobenzoate hydrate, C23H25F2N3O6
  32. Crystal structure of [diaqua-{1H-benzo[d]imidazol-3-ium-5,6-dicarboxylato-κ2O,O′}magnesium(II)] C18H14MgN4O10
  33. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl) (2-iodo-5-methoxyphenyl)methanone, C20H20INO5
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  36. Crystal structure of 2-chloro-5-((5-isopropyl-2-methylphenoxy)methyl)pyridine, C16H18ClNO
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