Startseite Crystal structure of 5-methyl-3,3-diphenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C25H25NO2S
Artikel Open Access

Crystal structure of 5-methyl-3,3-diphenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C25H25NO2S

  • Xie Huang , Ping-an Wang , Wei He und Xiaoxia Ye
Veröffentlicht/Copyright: 16. März 2018

Abstract

C25H25NO2S, monoclinic, P21 (no. 4), a = 9.371(4) Å, b = 11.397(4) Å, c = 9.777(4) Å, β = 95.117(6)°, V = 1040.0(7) Å3, Z = 2, Rgt(F) = 0.0423, wRref(F2) = 0.0921, T = 296(2) K.

CCDC no.: 1579290

The title structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Block, colorless
Size:0.39 × 0.30 × 0.17 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.18 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:25.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:5068, 3373, 0.025
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2874
N(param)refined:264
Programs:Bruker programs [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
S10.75726(9)0.25438(6)0.78180(7)0.0423(2)
N10.7289(2)0.2942(2)0.6209(2)0.0393(6)
O10.6424(2)0.17697(18)0.8069(2)0.0542(6)
O20.9025(2)0.2161(2)0.8022(2)0.0602(7)
C10.7110(4)0.7004(3)1.1058(4)0.0701(11)
H1A0.80400.72261.14680.105*
H1B0.64700.69021.17630.105*
H1C0.67470.76081.04360.105*
C20.7223(3)0.5872(3)1.0285(3)0.0449(8)
C30.6010(3)0.5315(3)0.9699(3)0.0477(8)
H30.51150.56380.98030.057*
C40.6100(3)0.4296(3)0.8967(3)0.0436(7)
H40.52730.39300.85820.052*
C50.7422(3)0.3820(2)0.8808(2)0.0342(6)
C60.8644(3)0.4348(3)0.9405(3)0.0444(8)
H60.95370.40140.93150.053*
C70.8540(3)0.5371(3)1.0135(3)0.0494(8)
H70.93670.57291.05320.059*
C80.8287(3)0.3717(3)0.5678(3)0.0444(8)
H80.91780.38160.61650.053*
C90.8003(3)0.4302(3)0.4526(3)0.0411(7)
C100.6593(3)0.4179(3)0.3693(3)0.0430(8)
H10A0.67480.42080.27250.052*
H10B0.59860.48370.38870.052*
C110.5819(3)0.3033(3)0.3987(2)0.0351(6)
C120.5811(3)0.3008(3)0.5577(3)0.0403(7)
H12A0.53530.37110.58870.048*
H12B0.52720.23340.58490.048*
C130.9056(4)0.5146(4)0.4000(3)0.0661(10)
H13A0.99120.51600.46160.099*
H13B0.86420.59170.39400.099*
H13C0.92860.49010.31060.099*
C140.4247(3)0.3014(3)0.3381(3)0.0370(6)
C150.3631(3)0.3923(3)0.2617(3)0.0469(8)
H150.41820.45760.24410.056*
C160.2206(4)0.3886(3)0.2103(4)0.0635(10)
H160.18130.45140.15920.076*
C170.1372(4)0.2940(3)0.2338(4)0.0625(10)
H170.04170.29140.19880.075*
C180.1975(4)0.2028(3)0.3102(4)0.0586(9)
H180.14200.13790.32830.070*
C190.3381(3)0.2063(3)0.3598(3)0.0494(8)
H190.37690.14270.40980.059*
C200.6597(3)0.1964(3)0.3463(3)0.0337(6)
C210.7077(3)0.1977(3)0.2154(3)0.0503(8)
H210.69470.26490.16180.060*
C220.7735(4)0.1021(4)0.1641(3)0.0612(10)
H220.80630.10580.07720.073*
C230.7913(4)0.0020(3)0.2387(4)0.0615(10)
H230.8356−0.06260.20270.074*
C240.7435(3)−0.0037(3)0.3687(4)0.0554(9)
H240.7544−0.07230.42020.066*
C250.6796(3)0.0937(3)0.4204(3)0.0446(7)
H250.64890.09010.50820.053*

Source of material

The mixture of 3-chlorobenzoperoxoic acid and 1-iodo-4-methylbenzene in CH2Cl2 was stirred at 0 °C for 30 min and BF3⋅Et2O was added to continue the reaction for 1 h. 4-Methyl-N-(4-methyl-2,2-diphenylpent-4-en-1-yl)benzenesulfonamide was added to the reaction solution for an additional 1 h at room temperature and then the reaction mixture was evaporated. The residue was purified by flash column chromatography (petroleum ether/ethyl acetate = 46/1) to afford the desired product.

Experimental details

The Uiso values of the hydrogen atoms of methyl groups were set to 1.5 Ueq(C). The Uiso values of phenyl, methylene hydrogen atoms were set to 1.2 Ueq(C).

Discussion

Nitrogen-containing heterocyclic compounds are valuable in pharmaceutical chemistry [3], [4], [5], [6]. The title structure can easily be converted into a series of compounds containing a piperidine ring due to the activity of the C=C bonds [7, 8] . They are widely used in antitumor [9], anti-inflammatory [10], anxiety [11], anticonvulsant [12] studies.

In the title structure, the 1,2,3,4-tetrahydropyridine ring adopts a chair conformation. The dihedral angles between the plane 3 of sulfonyl group (O1, S1 and O2) and the plane 1 of phenyl (C14, C15, C16, C17, C18 and C19), the plane 2 of phenyl (C20, C21, C22, C23, C24 and C25), and its connected plane 4 of phenyl (C2, C3, C4, C5, C6 and C7) are 19.64(1)°, 63.87(9)°, 50.82(1)°, respectively. Besides, the dihedral angle between two phenyl rings (plane 1 and plane 2) directly connected the 1,2,3,4-tetrahydropyridine ring is 79.78(9)°, and the dihedral angles between the plane 4 and plane 1, plane 2 are 58.93(8)°, 88.15(8)°, respectively. No hydrogen bonds were found.

Acknowledgements

We acknowledge the funding support received from the National Major Scientfic and Technogical Special Project for Essential New Drugs Development (No. 2014ZX09J1410406C).

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Received: 2017-11-12
Accepted: 2018-3-7
Published Online: 2018-3-16
Published in Print: 2018-5-24

©2018 Xie Huang et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Bis(tetraethylammonium) carbonate – boric acid – water (1/2/5), C17H56B2N2O14
  3. Crystal structure of 4-methoxy-6-phenyl-2H-pyran-2-one, C12H10O3
  4. Crystal structure of tris{(3-((E)-(((E)-2-oxidobenzylidene)hydrazono)methyl)-2-oxo-2H-chromen-4-olato-κ3O,N:N′)}dicobalt(III)tris(dimethylformamide), C60H50Co2N9O15
  5. Crystal structure of poly[bis(1-methyl-[4,4′-bipyridin]-1-ium-κN)-tetrakis(μ3-sulfato-κ3O:O′:O′′)trizinc(II)], C22H22Zn3N4O16S4
  6. Crystal structure of (5Z,10Z)-3,13-dichloro-17,18-dioxo-5,11-diphenyl-8,9,17,18-tetrahydro-7H-dibenzo[e,n][1,4,8,12]tetraazacyclopentadecine-16,19-diido-κ4N,N′,N′′,N′′′)copper(II), C31H22N4O2Cl2Cu
  7. Crystal structure of bis{5-methoxy-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2N,O}zinc(II), C34H24N2O8Zn
  8. Crystal structure of 2,2′-((((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))diphenolato-κ2N4O)nickel(II), C28H22N2O4Ni
  9. Crystal structure of 1,1′-((1E,1′E)-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(naphthalen-2-olato)cobalt(II), C36H26N2O4Co
  10. Crystal structure of camptothecin, C20H16N2O4
  11. Crystal structure of (2-(chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato–κ2O,O′)(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, Ni(C16H36N4)(C12H12O4Cl)ClO4⋅H2O
  12. Crystal structure of 3-(2-chloro-6-methoxyquinolin-3-yl)-5-phenylisoxazole (C19H13ClN2O2)
  13. Crystal structure of tetrakis(μ2-acetato-κ2O:O′)-bis{[(E)-2,6-diisopropyl-N-(pyridin-3-ylmethylene)aniline]copper (II)}, C44H56Cu2N4O8
  14. Crystal structure of diethyl 2-(2-chlorophenyl)-1,3-dioxane-5,5-dicarboxylate, C16H19Cl1O6
  15. Crystal structure of (μ2-2,2′-bipyridine-3,3′-dicarboxylato)-bis(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane)-di-nickel(II) perchlorate N,N′-dimethylformamide solvate, C50H92Cl2N12Ni2O14
  16. Crystal structure of catena-poly[triaqua(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′)-(1,2-bis(4-pyridyl)ethane-κN)nickel(II)] 2-aminonicotinate nitrate – 1,2-bis(4-pyridyl)ethane – water (2/1/8), C36H44N8NiO12
  17. Hydrothermal synthesis and crystal structure of poly[bis(μ2-3-(3,5-dicarboxyphenoxy)phthalato-κ3O,O′:O′′)-(μ2-1,2-di(pyridin-4-yl)ethane-κ2N:N′)copper(II)], C22H14CuNO9
  18. Crystal structure of catena-poly[aqua-(methanol-κO)-bis(μ2-4-(pyridin-4-yl)benzoato-κ2N:O)-bis(triphenylphospine-κP)disilver(I)], C61H52Ag2N2O6P2
  19. The crystal structure of 6-(4-bromobenzyl)-1,3,5-trimethyl-7-phenyl-1,5-dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-dione, C22H20BrN3O2
  20. Synthesis and crystal structure of catena-poly[bis(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetato-κO2O′,O′′)-(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)zinc(II)], C44H32N4ZnCl4O4
  21. Crystal structure of diaqua-bis[N-phenyl-2-(quinolin-8-yloxy)acetamide-κ3-N,O,O′]-nitrato(κ2O,O′)-cerium(III) dinitrate - acetone (1/2), C40H44N7O17Ce
  22. Crystal structure of the 2D coordination polymer poly[aqua(μ2-2,2′-(1,2-phenylene)diacetato-κ3O,O′:O′)-(μ2-4,4′-bis((1H-1,2,4-triazol-1-yl)methyl)-1,1′-biphenyl-κ2N:N′)cobalt(II)], C28H26CoN6O5
  23. Crystal structure of (dimethylformamide-κO)(perchlorato-κ2O,O′){μ2-6,6′-((1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(4-bromo-2-methoxyphenolate)-κ8N,N′,O:O,O′:O′,O′′,O′′′}sodium(I)nickel(II), C25H23Br2ClN3NaNiO9
  24. The crystal structure of catena-poly[bis((4-aminophenyl)sulfonyl)(pyrimidin-2-yl)amido-κ2N,N′)-bis(μ2-4,4′-bipyridine-N,N′2N:N′)zinc(II) – methanol (1/2), C32H34N10O6S2Zn
  25. Synthesis and crystal structure poly[aqua(μ3-2-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)acetate-κ4O,O′:O′′:O′′′) sodium] monohydrate, C18H18NNaO11S
  26. Crystal structure of methyl 4′-amino-3′,5′-diisopropyl-[1,1′-biphenyl]-4-carboxylate, C20H25NO2
  27. Crystal structure of (η6-1-isopropyl-4-methyl benzene)-(N-(2,5-dichlorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) perchlorate, C22H22Cl4N2O4Ru
  28. Crystal structure of 2-(2-(1-Chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1H-1,2,4-triazole-3(2H)-thione, C14H15Cl2N3OS
  29. Crystal structure of methyl 4′-amino-3′,5′-dimethyl-[1,1′-biphenyl]-4-carboxylate, C16H17NO2
  30. The crystal structure of 1-(5-ferrocenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pentan-1-on, C19H19F3FeN2O
  31. The crystal structure of (3S,12R,20R,24S)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25-triol acetone solvate, C34H56O6
  32. Crystal structure of methyl 10-(pyridin-4-yl)-anthracene-9-carboxylate, C21H15NO2
  33. Crystal structure of catena-poly[diaqua-bis(di(N2,N6-dihydroxypyridine-2,6-dicarboxamide))potassium(I)]tetrahydrate, C14H25N6O14K
  34. Crystal structure of poly{[μ2-(E)-1,4-bis(1H-benzo[d]imidazol-1-yl)but-2-ene-κ2N:N′][μ3–cyclohexane-1,4-dicarboxylato-κ4O,O′:O′′:O′′′]cadmium(II)}, C26H26CdN4O4
  35. Crystal structure of poly[aqua(μ3-[2,2′-bipyridine]-3,3′-dicarboxylato-κ4N,N′:O:O′)zinc(II)] – dimethylformamide (1/1), C15H15N3O6Zn
  36. The crystal structure of poly[tetraaqua-tris(μ2-2,6-di(1H-imidazol-1-yl)naphthalene-κ2N:N′)-bis(thiophene-2,5-dicarboxylato-κ1O)]dicobalt(II), C30H24CoN6O6S
  37. Crystal structure of (S)-1-(5-(anthracen-9-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O
  38. Crystal structure of 5-methyl-3,3-diphenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C25H25NO2S
  39. Synthesis and crystal structure of μ-[1,1′-di(mesitylphosphanido)ferrocene]bis[η5-cyclopentadienylnickel(II)] tetrahydrofurane solvate, C42H48FeNi2OP2
  40. Synthesis and crystal structure of (E)-1-(4-(((E)-5-chloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15ClN2O2
  41. Crystal structure of bis(1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O)nickel(II), C24H22N8O4S2Ni
  42. Crystal Structure of bis(1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O)copper(II), C24H22N8O4S2Cu
  43. Synthesis and crystal structure of poly[aqua{μ3-(1S,2S)-1-((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)pyrrolidin-1-ium-2-carboxylato-κ4O,O′:O′′:O′′′}sodium(I)] monohydrate, C21H22NNaO11S
  44. Halogen bonds in the crystal structure of 1,4-diiodotetrafluorobenzene–1,2-bis(4-pyridyl)propane (1/1), C19H14F4I2N2
  45. Crystal structure of bis(μ-N-i-propyl-N-n-propyldithiocarbamato-κ2S:S′) bis(N-i-propyl-N-n-propyldithiocarbamato-κ2S,S′)dizinc(II), C28H56N4S8Zn2
  46. Crystal structure of bis(μ-N-i-propyl-N-n-propyldithiocarbamato-κ3S,S′:S)bis(N-i-propyl-N-n-propyldithiocarbamato-κ2S,S′)dicadmium(II), C28H56Cd2N4S8
  47. Crystal structure of bis(μ2-di-n-butyldithiocarbamato-κ3S,S′:S3S:S:S′)-hexacarbonyl-di-rhenium(I), C24H36N2O6Re2
  48. Crystal structure of 7-(4-methylphenyl)imidazo[1,2-a][1,3,5]triazin-4-amine, C12H11N5
  49. Crystal structure of the co-crystal O-isopropyl phenylcarbamothioate – 4,4′-bipyridine (2/1), C15H17N2OS
  50. Crystal structure of the coordination polymer catena-poly[chlorido-{μ2-2-(((3,5-dimethyl-1H-pyrazol-1-yl)methyl)amino)-3-hydroxybutanoato-κ4N,N,O:O′}copper(II)], C11H16ClCuN2O3
  51. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-di(ethanol)-bis{μ2-5-(N,N′-diethylamine)-5′-methoxyl-2,2′-[ethylenediyldioxybis(nitrilomethylidyne)]diphenolato-κ6O:O,N,N,O′:O′}trinickel(II) – ethanol – acetonitrile (1/2/2), C58H86Ni3N8O18
  52. Crystal structure of the bis((E)-O-ethyl-N-phenylthiocarbamate) – 4,4′-bipyridine co-crystal (2/1), C28H30N4O2S2
  53. Crystal structure of the (E)-O-methyl-N-phenyl-thiocarbamate – 4,4′-bipyridine (1/1), C18H17N3OS
  54. Crystal structure of bis(μ2-diethyldithiocarbamato-κ3S,S′:S′)-bis(tricyclohexylphosphane-κP)dicopper(I), C46H86Cu2N2P2S4
  55. Crystal structure of N-(3-chlorophenyl)ethoxycarbothioamide, C9H10ClNOS
  56. Crystal structure of bis(μ2-pyrrolidine-1-carbodithioato-κ3S,S′:S;κ3S:S:S′)-bis(tricyclohexylphosphane-P)-di-copper(I), C46H82Cu2N2P2S4
  57. Crystal structure of N-(2-chlorophenyl)methoxycarbothioamide, C8H8ClNOS
  58. Crystal structure of chlorido-methanol-(N-(2-(oxy)-3-methoxybenzylidene)pyridine-4-carbohydrazonato-κ3O,N,O′)-(4-methylphenyl)methyl-tin(IV), C23H24ClN3O4Sn
  59. Crystal structure of N-(3-chlorophenyl)(propan-2-yloxy)carbothioamide, C10H12ClNOS
  60. Crystal structure of 1-[(Z)-[4-(4-methoxyphenyl)butan-2-ylidene]amino]-3-phenylurea, C18H21N3O2
  61. A triclinic polymorph of bis(μ-N,N-bis(2-hydroxyethyl)dithiocarbamato-κ3S,S′:S′) bis(N,N-bis(2-hydroxyethyl)dithiocarbamato-κ2S:S′)zinc(II), C20H40N4O8S8Zn2
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