Startseite Naturwissenschaften (E)-N-benzylidene-3-(benzylthio)-5-p-tolyl-4H-1,2,4-triazol-4-amine, C23H20N4S
Artikel Open Access

(E)-N-benzylidene-3-(benzylthio)-5-p-tolyl-4H-1,2,4-triazol-4-amine, C23H20N4S

  • Qichun Ding EMAIL logo , Shudong Dai , Hongxu Guo und Li-Xue Zhang
Veröffentlicht/Copyright: 16. September 2017

Abstract

C23H20N4S, Monoclinic, P21/n (no. 14), a = 11.439(3) Å, b = 8.868(2) Å, c = 20.557(5) Å, β = 104.542(4)°, V = 2018.7(8) Å3, Z = 4, Rgt(F) = 0.0449, wRref(F2) = 0.1266, T = 298(2) K.

CCDC no.:: 1571326

The crystal structure is shown in the figure. 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:Block, colourless
Size:0.36 × 0.32 × 0.23 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.18 mm−1
Diffractometer, scan mode:CCD area detector, φ and ω-scans
2θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:9888, 3556, 0.038
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2470
N(param)refined:254
Programs:Bruker programs [1], SHELX [2]
Table 2

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

AtomxyzUiso*/Ueq
S10.39452(6)0.19481(7)1.06911(3)0.0731(2)
N10.25824(15)0.0537(2)0.92820(8)0.0571(5)
N20.36849(15)0.12915(18)0.93655(8)0.0541(4)
N30.52124(16)0.2780(2)0.97885(9)0.0674(5)
N40.51494(16)0.2532(2)0.91147(9)0.0658(5)
C10.2988(2)−0.0072(3)0.60699(12)0.0889(8)
H1A0.35740.03440.58580.133*
H1B0.22030.03160.58550.133*
H1C0.2984−0.11500.60300.133*
C20.3308(2)0.0362(3)0.68024(11)0.0653(6)
C30.2611(2)−0.0092(3)0.72176(12)0.0723(7)
H3A0.1928−0.06740.70430.087*
C40.2892(2)0.0290(3)0.78859(12)0.0699(6)
H4A0.2401−0.00460.81540.084*
C50.38836(18)0.1159(2)0.81662(10)0.0550(5)
C60.4582(2)0.1619(3)0.77435(13)0.0774(7)
H6A0.52600.22140.79130.093*
C70.4294(2)0.1216(3)0.70820(13)0.0827(8)
H7A0.47890.15360.68130.099*
C80.42279(18)0.1655(2)0.88644(10)0.0542(5)
C90.43295(19)0.2019(2)0.99276(11)0.0573(5)
C100.4673(3)0.3600(3)1.11014(13)0.0893(8)
H10A0.55440.34761.12160.107*
H10B0.44640.44731.08110.107*
C110.4237(2)0.3792(3)1.17174(12)0.0679(6)
C120.4786(3)0.3052(3)1.22924(14)0.0918(8)
H12A0.54540.24501.22990.110*
C130.4384(4)0.3169(4)1.28539(16)0.1119(11)
H13A0.47830.26541.32400.134*
C140.3431(4)0.4004(4)1.28632(17)0.1066(10)
H14A0.31620.40621.32530.128*
C150.2842(3)0.4778(4)1.2307(2)0.1121(11)
H15A0.21730.53691.23120.134*
C160.3261(3)0.4670(3)1.17264(16)0.0969(9)
H16A0.28720.52001.13430.116*
C170.25665(19)−0.0428(2)0.97358(11)0.0548(5)
H17A0.3272−0.06111.00670.066*
C180.14831(19)−0.1250(2)0.97532(10)0.0525(5)
C190.1537(2)−0.2272(2)1.02667(11)0.0631(6)
H19A0.2262−0.24271.05860.076*
C200.0524(2)−0.3060(3)1.03067(12)0.0712(7)
H20A0.0562−0.37401.06560.085*
C21−0.0535(2)−0.2844(3)0.98356(12)0.0718(7)
H21A−0.1220−0.33800.98630.086*
C22−0.0595(2)−0.1838(3)0.93209(12)0.0711(6)
H22A−0.1320−0.16960.90000.085*
C230.0407(2)−0.1045(2)0.92790(11)0.0612(6)
H23A0.0362−0.03650.89290.073*

Source of material

The title compound was prepared by the reaction of (E)-4-(benzylideneamino)-3-p-tolyl-1H-1,2,4-triazole-5(4H)-thione (2 mmol) and (bromomethyl)benzene (2 mmol) in the mixture of ethanol (40 mL) and triethylamine (1 mL). The mixture was stirred at room temperature for 10 min and the product was obtained by filtration, drying and recrystallization from ethanol. Crystals suitable for X-ray data collection were obtained by slow evaporation of a ethanol solution after 10 days. (E)-4-(benzylideneamino)-3-p-tolyl-1H-1,2,4-triazole-5(4H)-thione was synthesized by the reaction of 4-amino-3-p-tolyl-1H-1,2,4-triazole-5(4H)-thione (2 mmol) and benzaldehyde (2 mmol) with concentrated hydrochloric acid (1 mL) in ethanol (40 mL) refluxed for 3 h.

Experimental details

All H atoms were positioned geometrically and allowed to ride on their parent atoms at distances of Csp2–H = 0.93 Å with Uiso = 1.2Ueq (parent atom), and Csp3–H = 0.96 or 0.97 Å with Uiso = 1.5Ueq (parent atom).

Discussion

In recent decades, compounds containing the 1,2,4-triazole group have attracted much interest because of their exhibiting various biological activities [3], [4], [5], [6], [7]. Recently, (E)-3-substituted-4-arylideneamino-5-arylthiol (or alkylthiol)-4H-1,2,4-triazoles have been reported to possess antioxidant, herbicidal, antifungal antineoplastic, and etc [6].

The bond lengths and angles are in the usual ranges. The triazole ring and the benzene ring (C2—C7) are essentially planar and the dihedral angle between them is 2.93(0.15)°. The phenyl ring C18—C23 and the other two aryl moieties (C2—C7 and C11—C16) form two dihedral angles of about 50°. The two rings C2—C7 and C11—C16 are approaching mutually perpendicular, and the dihedral angle between them is 72.29(0.07)°. Both the S—C and C—N bond lengths are in good agreement with the values observed in related compounds. The short C—N bond lengths of 1.304(3) Å for N3—C9 and 1.307(3) Å for N4—C8, respectively, suggest partially localized double bonds.

Acknowledgement

This work was supported by the Education Scientific Research Project of Young Teachers of Fujian Province (B), China (Project No. JB14208) and the Zhangzhou Health Vocational College Project of China (Project No. ZYZ201402).

References

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Received: 2017-5-9
Accepted: 2017-8-29
Published Online: 2017-9-16
Published in Print: 2017-11-27

©2017 Qichun Ding 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. Crystal structure of potassium 1-methyl-1H-1,2,3,4-tetrazole-5-thiolate, C2H3N4SK
  3. Crystal structure of bis(3-(3-ethylureido)-N,N-dimethylpropan-1-aminium) bis (μ3-2-(hydroxymethyl)-2-(oxidomethyl)propane-1,3-bis(olato))-(μ6-oxo)-hexakis(μ2-oxo)-hexaoxo-hexavanadium(V) – dichloromethane (1/1), C27H60Cl2N6O23V6
  4. Crystal structure of bis(μ3-methanolato-κ3O:O:O)-bis(μ2-methanolato-κ2O:O)-dimethanol-bis{6,6′-(1,3-dihydroxyl-2-acetylpropane-1,3-diyl)bis(2-chloro-4-bromophenolato)}tetramanganese(III) C40H40Br4Cl4Mn4O16
  5. Synthesis and crystal structure of tetrakis(μ2-methanolato)-dimethanol-bis(μ2-2-acetyl-1,3-bis(3,5-dibromo-2-oxidophenyl)propane-1,3-bis(olato)-κ5O1,O2,O3:O3,O4,O5)tetramanganese(III), C40H40Br8Mn4O16
  6. Synthesis and crystal structure tetrakis(μ2-methanolato)-dimethanol-bis(μ2-2-acetyl-1,3-bis(3,5-dichloro-2-oxidophenyl)propane-1,3-bis(olato)-κ5O1,O2,O3:O3,O4,O5), tetramanganese(III), C40H40Cl8Mn4O16
  7. Crystal structure of bis{5-methoxy-2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O)}copper(II), C34H34CuN4O6
  8. Crystal structure of (E)-1-(2-hydroxy-3-{[2-hydroxybenzylidene]amino}phenyl)ethan-1-one, C15H13NO3
  9. Crystal structure of bis(μ2-acetato-κ2O:O′)-bis{μ2-4-chloro-2-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ6O:O,N,N′,O′′:O′′}tricobalt(II), C44H49Cl2Co3N6O12
  10. Crystal structure of bis{μ2-2,4-dichloro-6-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ5O:O,N,N′,O′}dicobalt(II) acetone solvate, C43H48Br4Co2N6O9
  11. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-bis{μ2-4-chloro-2-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ6O:O,N,N′,O′:O′}trizinc(II), C44H49Cl2N6O12Zn3
  12. Crystal structure of bis{5-(N,N′-diethylamine)-5′-methoxy -2,2′-[ethylenediyldioxybis(nitrilomethylidyne)]diphenolato}-bis(μ2-acetato-κ2O:O′)trizinc(II), C46H56Zn3N6O14
  13. Crystal structure of tris(cyano-(hydrogen tris(3,5-dimethylpyrazolyl)borate))-iron(III) 4-methoxypyridinium monohydrate, C24H32BN10O2Fe
  14. Synthesis and crystal structure of bis{1-(((4-(1-(hydroxyimino)ethyl)phenyl)imino)methyl)naphthalen-2-olato-κ2O,N}copper(II), C38H30CuN4O4
  15. Crystal structure of (E)-1-(4-{[(E)-2-Hydroxy-1-naphthalenylmethylene] amino}phenyl)ethanone oxime, C19H16N2O2
  16. The pseudosymmetric crystal structure of 2-(2-naphthalenyl)-3-nitro-2H-1-benzopyran, C38H26N2O6
  17. Crystal structure of 2-benzoyl-3-(4-methoxyphenyl)cyclopropane-1,1-dicarbonitrile, C19H14N2O2
  18. N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide monohydrate, C17H21N3O5
  19. The crystal structure of carbonyl-[4-(2,4-dichlorophenylamino)pent-3-en-2-onato-κ2N,O]-(triphenylphosphine-κP)rhodium(I), RhC30H25Cl2NO2P
  20. Crystal structure of (E)-5-(diethylamino)-2-(((1,1,2-trihydroxyethyl)iminio)methyl)phenolate, C15H24N2O4
  21. Crystal structure of poly[(μ2-1,4-bis((2-ethyl-1H-benzo[d]imidazol-1-yl)methyl)benzene-κ2N:N′)(μ2-isophthalato-κ4O,O′:O′′,O′′′)cadmium(II)], C34H30N4O4Cd
  22. Crystal structure of 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]chinolizinium 3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate - methanol - water (1/1/1), C36H33NO10
  23. A single crystal study on 2-(methylcarbamoyl)benzoic acid, C9H9NO3
  24. Crystal structure of the salt 1,1′-(ethane-1,2-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) diperchlorate, C14H28N4(ClO4)2
  25. Crystal structure of 2,5-bis((E)-2-(trifluoromethyl)benzylidene)cyclopentan-1-one, C21H14F6O
  26. Crystal structure of catena-poly[(μ2-benzene-1,4-dicarboxylato-κ2O:O′)-(1-ethyl-6-fluoro-7-(4-methylpiperazin-1-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylato-κ2O,O′)zinc(II)] 1.25 hydrate, C25H26.5N3O8.25FZn
  27. Crystal structure of 1-methyl-1,4-diazabicyclo[2.2.2]octan-1-ium poly[aqua-bis(μ2-perchlorato-κ3O,O′:O′′)sodium], C7H17Cl2N2NaO9
  28. Crystal structure of trimethyammonium 2,6-dicarboxyisonicotinate monohydrate, C11H16N2O7
  29. Crystal structure of dodecaguanidinium bis(tetrapropylammonium) heptacarbonate, C43H128N38O21
  30. Crystal structure of poly[tetraaqua-bis(μ6-benzene-1,2,4,5-tetracarboxylato)nickel(II)diyttrium(III)]dihydrate, C20H16NiO22Y2
  31. Halogen bonds and π–π interactions in the crystal structure of 1,3,5-trifluoro-2,4,6-triiodobenzene–N,N-dimethylformamide (1/1), C9H7F3I3NO
  32. Crystal structure of guanidinium tetraethylammonium carbonate dihydrate, C10H30N4O5
  33. The crystal structure of oxonium chlorido-ethylenediaminetetraactetotin(IV) hydrate, C10H17ClN2O10Sn
  34. Crystal structure of 8-((E)-((4-((E)-1-((benzyloxy)imino)ethyl)phenyl)imino)methyl)-7-hydroxy-4-methyl-2H-chromen-2-one, C26H22N2O4
  35. Crystal structure of bis{5-(diethylamino)-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2O,N}copper(II), C40H38CuN4O6
  36. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(tri(p-tolyl)phosphine-κP)rhenium(I), C29H28O5PRe
  37. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(benzyldiphenylphosphine-κP)rhenium(I), C27H24O5PRe
  38. Crystal structure of triethylammonium bis{3-(((3-oxidonaphthalen-1-yl)methylene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}manganese(III), C46H38MnN3O8
  39. Crystal structure of bis(N,N,N-ethyldimethylethanaminium) bis(heptaselenido-κ2Se1,Se7)palladate(II), C12H32N2PdSe14
  40. Crystal structure of bis(4-(1H-pyrazol-5-yl)pyridine-κ2N:N′)-bis(2-(2-((2,6-difluorophenyl)amino)phenyl)acetate-κO)cadmium(II), C44H34N8CdCl4O4
  41. Crystal structure of 4,4′-(1,4-phenylene)bis(pyridin-1-ium) catena-poly[diaqua-bis(μ2-3′,5′-dicarboxy-[1,1′-biphenyl]-2,5-dicarboxylato-κ2O:O′] dihydrate, C48H42O22N2Ca
  42. The crystal structure of (S)-2-benzylsuccinic acid, C11H12O4
  43. Crystal structure of poly[aqua-(μ3-4-(pyridin-4-yl)isophthalato-κ4O,O′:O′′:O′′′)-(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:O′)yttrium(III)], C26H17N2O9Y
  44. Crystal structure of ethyl 1-(3,4-dimethylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate, C14H17N3O2
  45. Crystal structure of tetrakis(methanol-κO)-bis{μ2-3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olate-κ4O,N;O′:O′}dizinc(II), C38H38Zn2N2O14
  46. Crystal structure of bromido(4,4′-dimethoxy-2,2′-bipyridine-κ2N,N′)(isopropyl(diphenyl)phosphane-κP)copper(I), C27H29BrCuN2O2P
  47. Crystal structure of bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9,9-dioctylfluorene, C41H64B2O4
  48. Crystal structure of 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carbaldehyde - a julolidine derivative, C16H15NO3
  49. Crystal structure of 1,3-dimethyl-5,5-dibenzylbarbituric acid, C20H20N2O3
  50. Crystal structure of bis(N,N,N-trimethylethanaminium) poly[bis(μ2-heptaselenido-κ2Se1,Se7)palladate(II)], C10H28N2PdSe14
  51. Crystal structure of 1-{4-[(5-Chloro-2-hydroxy-benzylidene)amino]phenyl} ethanone O-ethyl-oxime, C17H17ClN2O2
  52. The crystal structure of methyl N-(4-bromophenyl)carbamate, C8H8BrNO2
  53. Synthesis and crystal structure of 1-{4-[(2-hydroxy-benzylidene)amino]phenyl}ethanone oxime, C15H14N2O2
  54. Crystal structure of 1,1′-butanebis(3-methyl-1H-imidazol-3-ium)bis(hexafluorophosphate), C12H20F12N4P2
  55. (E)-N-benzylidene-3-(benzylthio)-5-p-tolyl-4H-1,2,4-triazol-4-amine, C23H20N4S
  56. Crystal structure of ethyl 5-methyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate, C11H12N4O2
  57. Crystal structure of 5,5-difluoro-10-(4-fluorophenyl)-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine - a Z′ = 3 structure, C19H18B2F3N2
  58. The crystal structure of the Matrine derivative: 12-(1H-indol-1-yl)dodecahydro-1H,5H,10H-dipyrido[2,1-f:3′,2′,1′-ij][1,6]naphthyridin-10-one hydrate, C23H29N3O
  59. The crystal structure of tris(μ2-1,3-bis(4,4,4-trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-κ2O,O′)dilutetium(III), C50H38F18Lu2O16
  60. The crystal structure of (Z)-2-(3-(2-(4-chlorobenzoyl)hydrazono)-2-oxoindolin-1-yl) acetic acid, C17H12ClN3O4
  61. Synthesis and crystal structure of trans-tetraqua-bis(2-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)acetato-κO)cobalt(II) hexahydrate, C36H48CoN2O28S2
  62. The crystal structure of N,N-dimethyl-2,6-di-p-tolylpyrimidin-4-amine, C20H21N3
  63. The crystal structure (E)-4-methyl-N′-(2-nitrobenzylidene)benzenesulfonohydrazide, C14H13N3O4S
  64. Crystal structure of catena-poly[(μ2-1,3-bis(benzimidazol-1-yl)propane κ2N:N′)-(μ2-5-methoxyisophthalato-κ2O:O′)zinc(II)] hydrate, C26H24ZnN4O6
  65. The crystal structure of (E)-N′-(quinolin-2-ylmethylene)furan-2-carbohydrazide monohydrate, C15H13N3O3
  66. Crystal structure of 2,8-diphenyl-3,7,9-trioxa-1-azaspiro[4.5]dec-1-ene, C18H17N1O3
  67. Crystal structure of diethyl 2-(4-chlorophenyl)-1,3-dioxane-5,5-dicarboxylate, C16H19ClO6
  68. Crystal structure of 1-(carboxymethyl)-1H-benzo[d][1,2,3]triazole 3-oxide, C8H7N3O3
  69. Crystal structure of (acetylacetonato-κ2O,O′)-(2-amino-6-chlorobenzoato-κO)-oxido(1,10-phenanthroline-κ2N,N′)vanadium(IV) – trichloromethane (1/1)
  70. Crystal structure of (1E,4E)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one, C17H12Cl2O
  71. The crystal structure of trans-dibromido-bis(pyridine-κN)platinum(II), C10H10Br2N2Pt
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