Home Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S
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Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S

  • Mona M. Al-Shehri , Tilal Elsaman , Ebtehal S. Al-Abdullah , Hazem A. Ghabbour and Ali A. El-Emam EMAIL logo
Published/Copyright: April 1, 2017
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 232 Issue 3

Abstract

C18H20FN3S, triclinic, P1̅, a = 7.3884(4) Å, b = 10.0741(6) Å, c = 12.6533(8) Å, α = 69.209(2)°, β = 73.778(2)°, γ = 72.638(2)°, V = 824.33(8) Å3, Z = 2, Rgt(F) = 0.0480, wRref(F2) = 0.1351, T = 296(2) K.

CCDC no.:: 1507728

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:Colourless block
Size:0.47 × 0.21 × 0.17 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:2.1 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:55°, >99%
N(hkl)measured, N(hkl)unique, Rint:38531, 3785, 0.057
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2741
N(param)refined:212
Programs:SHELX [24], [25], Bruker programs [26]
Table 2

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

AtomxyzUiso*/Ueq
S1−0.01552(8)0.59470(6)0.14514(5)0.04636(19)
F10.3030(3)0.6663(2)0.50902(18)0.1032(7)
N10.4015(2)0.28424(18)0.06263(15)0.0394(4)
N20.2347(3)0.38967(19)0.05035(16)0.0414(4)
N30.3230(2)0.40237(16)0.19199(13)0.0303(3)
C10.7369(3)0.0947(2)0.11679(18)0.0429(5)
H1A0.64950.04560.10490.051*
H1B0.78710.15900.04110.051*
C20.9053(3)−0.0196(2)0.16708(19)0.0435(5)
H2A0.9776−0.07760.11240.052*
C31.0395(3)0.0557(3)0.1828(3)0.0659(8)
H3A1.09010.12090.10760.079*
H3B1.1504−0.01740.21360.079*
C40.9291(4)0.1440(3)0.2664(3)0.0780(10)
H4A1.01830.19200.27920.094*
C50.7609(3)0.2606(2)0.2165(3)0.0573(7)
H5A0.69070.31920.26990.069*
H5B0.81160.32670.14180.069*
C60.6237(3)0.18627(19)0.19914(16)0.0306(4)
C70.8276(3)−0.1201(2)0.2804(2)0.0501(6)
H7A0.9357−0.19460.31320.060*
H7B0.7421−0.17060.26850.060*
C80.7150(4)−0.0324(3)0.3632(2)0.0631(8)
H8A0.6637−0.09920.43850.076*
C90.5461(3)0.0824(2)0.31396(19)0.0515(6)
H9A0.47210.13790.36910.062*
H9B0.45810.03410.30190.062*
C100.8472(5)0.0417(3)0.3820(3)0.0911(12)
H10A0.9546−0.03220.41590.109*
H10B0.77490.09850.43650.109*
C110.4548(3)0.29277(19)0.14938(16)0.0308(4)
C120.1802(3)0.4624(2)0.12725(17)0.0336(4)
C130.3284(3)0.4647(2)0.27702(16)0.0315(4)
C140.4012(3)0.5876(2)0.2401(2)0.0448(5)
H14A0.45560.62580.16120.054*
C150.3937(4)0.6551(3)0.3205(3)0.0611(7)
H15A0.44390.73970.29790.073*
C160.3123(4)0.5967(3)0.4329(3)0.0590(7)
C170.2403(3)0.4758(3)0.4709(2)0.0552(6)
H17A0.18750.43760.55010.066*
C180.2460(3)0.4094(2)0.39095(18)0.0413(5)
H18A0.19320.32580.41450.050*
H1N20.173(3)0.397(3)0.000(2)0.050(7)*

Source of material

4-Fluorophenyl isothiocyanate (1.53 g, 0.01 mol) was added to a solution of adamantane-1-carbohydrazide (1.94 g, 0.01 mol), in ethanol (10 mL), and the mixture was heated under reflux with stirring for one hour. The solvent was then distilled off in vacuo; an aqueous sodium hydroxide solution (10%, 15 mL) was added to the residue and the mixture was heated under reflux for two hours then filtered hot. On cooling, the mixture was acidified with hydrochloric acid (pH 1–2) and the precipitated crude product was filtered, washed with water, dried and crystallized from aqueous ethanol to yield 3.03 g (92%) of the title compound (C18H20FN3S) as fine transparent block crystals. M.P.: > 573 K. Single crystals were obtained by slow evaporation of a solution of the title compound in EtOH/CHCl3 (1:2) at room temperature. 1H-NMR (CDCl3, 500.13 MHz): δ 1.55–1.69 (m, 6H, adamantane-H), 1.86 (s, 3H, adamantane-H), 1.96 (s, 6H, adamantane-H), 7.24–7.32 (m, 4H, Ar—H), 11.89 (br. s, 1H, NH). 13C-NMR (CDCl3, 125.76 MHz): δ 27.85, 35.14, 36.72, 38.85 (adamantane-C), 118.22, 127.16, 132.51, 137.99 (Ar—C), 158.17 (triazole C = N), 171.11 (triazole C = S). EI-MS m/z (Rel. Int.): 329 (M+, 100).

Experimental details

Carbon-bound hydrogen atoms were placed in calculated positions and were included in the refinement using the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The position and Uiso of the nitrogen-bound hydrogen atom was freely refined.

Discussion

Various adamantane-based drugs have long been known as efficient medications for the control of several diseases [1, 2] . Amantadine [3], [4], [5], rimantadine [6] and tromantadine [7] are currently used as efficient antiviral drugs. Moreover, adamantane derivatives were also reported to exhibit marked anti-HIV [8], [9], [10], antibacterial [11], [12], [13], antimalarial [14], hypoglycemic [15, 16] , anti-inflammatory [17, 18] , and anticancer [19] activities. 1,2,4-Triazole derivatives were reported to possess significant anti-inflammatory [20, 21] and antibacterial [22] activities. The title compound was prepared as an adamantane-triazole hybrid derivative as potential bioactive agent [23]. The asymmetric unit of the title compound contains one independent molecule. Pairs of molecules pack in the crystal structure via one strong classical intermolecular hydrogen bond N2—H1N2⋯S1i. The D⋯A and H⋯A distances are 3.252(2) and 2.40(2) Å, respectively, and the D-H⋯A angle is 176(3)°. Symmetry code: (i) − x, − y + 1, − z.

Acknowledgement

The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for funding this work through the Research Group Project No. RG-1435-062.

References

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Received: 2016-10-6
Accepted: 2017-3-15
Published Online: 2017-4-1
Published in Print: 2017-5-24

©2017 Mona M. Al-Shehri et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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  50. Crystal structure of 4,4′-((1Z,1′Z)-2,2′-(2,5-diethoxy-1,4-phenylene)bis(ethene-2,1-diyl))dipyridine, C24H24N2O2
  51. Crystal structure of (16S)-12,16-epoxy-11,14-dihydroxy-17(15/16)-abeo-3a,18-cyclo-8,11,13-abietatrien-7-one, C20H24O4
  52. Crystal structure of aquadichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N,N′,N′′)nickel(II) monohydrate, C18H16Cl2N6NiO2
  53. Crystal structure of catena-poly[dichlorido-(μ-ethane-1,2-diyl-bis-(pyridyl-4-carboxylate-κN:N′)mercury(II)], C15H14Cl2HgN2O4
  54. Crystal structure of methyl 2-acetamido-5-chlorbenzoate, C10H10ClNO3
  55. Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8
  56. Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  57. Crystal structure of 4-(2-ammonioethyl)morpholin-4-ium dichloride monohydrate, C6H18Cl2N2O2
  58. Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2
  59. Crystal structure of 2-(4-(dimethylamino)-2-fluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol monohydrate, C15H20FN7O2
  60. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
  61. Crystal structure of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, C10H16
https://doi.org/10.1515/ncrs-2016-0309
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of 2,5-diiodo-4-nitro-1H-imidazole hemihydrate, C6H4I4N6O5
  3. Crystal structure of catena-poly[μ2-2,2′-(1,3-phenylene)diacetato-κ4O,O′:O′′,O′′′)-(μ2-1,6-bis(2-methyl-1H-benzo[d]imidazol-1-yl)hexane-κ2N:N′)cadmium(II)], C32H34CdN4O4
  4. Crystal structure of poly[aqua-(2,2′-bipyridine-κN,N′)-(μ4-5,5′-(hexane-1,6-diyl)-bis(oxy)diisophthalato κ8O1,O2:O3,O4:O5,O6:O7,O8)manganese(II)], C21H21MnN2O7
  5. Crystal structure of poly-[(μ2-((1,3-bis(benzimidazol-1-yl)propane-κ2N:N′)(μ2-4-tert-butyl-phthalato-κ2O:O′)cobalt(II)] monohydrate, C29H30CoN4O5
  6. Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-5-(oxo-5,6,7,8-tetrahydro-4H-chromene)-3-carbonitrile – ethanol (1/1), C21H26N2O6
  7. Crystal structure of ethyl 1-benzyl-5-phenyl-1H-pyrazole-3-carboxylate, C19H18N2O2
  8. Crystal structure of 2-(1-benzyl-3-phenyl-1H-pyrazol-5-yl)-5-(4-nitrobenzylthio)-1,3,4-oxadiazole, C25H19N5O3S
  9. Structure and photochromism of 1,2-bis[2-methyl-5-(2-chlorophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16Cl2F6S2
  10. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-4-ylmethylene)aniline, C18H22N2
  11. Crystal structure of (E)-2,4-dibromo-6-(((4-methyl-2-nitrophenyl)imino) methyl)phenol, C10H14Br2N2O3
  12. Crystal structure of (bis(2,2′-bipyridine-κ2N,N′))-(3,5-dinitrosalicylato-κ2O,O′)nickel(II), C27H18N6NiO7
  13. Crystal structure of 1-(diethoxy phosphonomethyl) 2-benzoyl-3-chloro-2-cyclohexen-1-ol, C18H24ClO5P
  14. Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C22H27CuN4O12.50
  15. Crystal structure of 1α,11-dihydroxyeremophil-9-en-8-one, C15H24O3
  16. Crystal structure of 1-ferrocenylsulfonyl-1H-imidazo[4,5-b]pyridine, C16H13FeN3O2S
  17. Crystal structure of bis(μ2-azido-κ2N:N)-dichlorido-bis(μ2-2-(pyridin-2-yl)ethan-1-ol-κ2O,N)dicopper(II), C14H18Cl2Cu2N8O2
  18. Crystal structure of (5,15-cis-bis(2-hydroxy-1-naphthyl)-10-phenyl-20-(4-hydroxyphenyl)-porphyrinato)-(pyridine)-zinc(ii) pyridine solvate, C67H47N7O3Zn
  19. Crystal structure of (μ2-[2,2′-bis(diphenylphosphino)-1,1′-binaphthalene oxide-κ2O,P])-iodido copper(I), C44H32CuIOP2
  20. Crystal structure of 6,8-diphenyl-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(3H)-one, C27H20FNO
  21. Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C68H104O4
  22. Crystal structure of N,N′–bis(pyridin-4-ylmethyl)pyrazine-2,3-dicarboxamide dihydrate, C18H20N6O4
  23. Crystal structure of a diaqua-bis(3,5-di(1H-imidazol-1-yl)pyridine-κN)-bis(2-(4-carboxy-phenyl)acetato-κO]manganese(II), C40H36MnN10O10
  24. Crystal structure of 4-(4-hydroxy-3-methoxy-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester, C21H25NO5
  25. Crystal structure of (E)-4,4′-(ethene-1,2-diyl)bis(3-nitrobenzoic acid) 1.5 hydrate, C16H13N2O9.5
  26. Crystal structure of (E)-2-(5-(4-fluorophenyl)-3-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-5-((4-fluorophenyl)diazenyl)-4-methylthiazole, C23H17F2N5OS
  27. Crystal structure of the co-crystalline adduct 4-((4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide - acetic acid (1/1), C21H24N4O4S ⋅ C2H4O2
  28. Synthesis and crystal structure of 2-((5-chlorobenzo[c][1,2,5]thiadiazol-4-yl)amino)-4,5-dihydro-1H-imidazol-3-ium tetraphenylborate, C33H29BClN5S
  29. Crystal structure of (4-chlorophenyl)(3-ferrocenyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)methanone, C21H14ClF3FeN2O
  30. Crystal structure of (S)-benzyl 3-(benzylcarba-moyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate, C25H24N2O3
  31. Crystal structure of 5-acetyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one, C15H17FN2O4
  32. Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16FIN2
  33. Crystal structure of methyl 1H-indole-2-carboxylate, C10H9NO2
  34. Crystal structure of 2,3-diphenyl-1-[(dipropylamino)acetyl]-1,3-diazaspiro[4.5]decan-4-one, C28H37N3O2
  35. Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3
  36. Crystal structure of 2,9-dibromo-1,10-phenanthroline, C12H6Br2N2
  37. Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S
  38. Crystal structure of trans-bis((E)-7-oxo-4-(phenyldiazenyl)cyclohepta-1,3,5-trien-1-olato)-κ2O,O′)-bis(pyridine-κN)cobalt(II), C36H28CoN6O4
  39. Crystal structure of 2-(4-methyl-3-phenylthiazol-2(3H)-ylidene)malononitrile, C13H9N3S
  40. Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C24H27ClN2S
  41. Crystal structure of chlorido{[3-(η5-cyclopenta-dienyl)-2,2,3-trimethyl-1-phenylbutylidene] azanido-κN}[η2(N,O)-N,N-dimethylhydroxylaminato]titanium(IV), C20H27ClN2OTi
  42. Crystal Structure of 1,1′-dimethyl-[4,4′-bipyridine]-1,1′-diium tetrachloridozincate(II), C12H14Cl4N2Zn
  43. Crystal structure of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde, C11H12N2O3
  44. Crystal structure of 2,3-diphenyl-1-(morpholin-4-ylacetyl)-1,3-diazaspiro[4.5]decan-4-one, C26H31N3O3
  45. Crystal structure of 3,3-dimethyl-3,4-dihydro-1H-benzo[c]chromene-1,6(2H)-dione, C15H14O3
  46. Crystal structure of bis(2-(2-hydroxymethyl)pyridine-κ2N,O)-bis(pivalato-κO)nickel(II), C22H32N2NiO6
  47. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(1H-pyrazole-3-carboxylato-κ2N,O)manganese(II) trihydrate, C20H20N6O7Mn
  48. The crystal structure of 3-aminopropan-1-aminium iodide, C3H11N2I
  49. Crystal structure of ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4 carboxylate, C12H12ClN3O2
  50. Crystal structure of 4,4′-((1Z,1′Z)-2,2′-(2,5-diethoxy-1,4-phenylene)bis(ethene-2,1-diyl))dipyridine, C24H24N2O2
  51. Crystal structure of (16S)-12,16-epoxy-11,14-dihydroxy-17(15/16)-abeo-3a,18-cyclo-8,11,13-abietatrien-7-one, C20H24O4
  52. Crystal structure of aquadichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N,N′,N′′)nickel(II) monohydrate, C18H16Cl2N6NiO2
  53. Crystal structure of catena-poly[dichlorido-(μ-ethane-1,2-diyl-bis-(pyridyl-4-carboxylate-κN:N′)mercury(II)], C15H14Cl2HgN2O4
  54. Crystal structure of methyl 2-acetamido-5-chlorbenzoate, C10H10ClNO3
  55. Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8
  56. Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  57. Crystal structure of 4-(2-ammonioethyl)morpholin-4-ium dichloride monohydrate, C6H18Cl2N2O2
  58. Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2
  59. Crystal structure of 2-(4-(dimethylamino)-2-fluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol monohydrate, C15H20FN7O2
  60. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
  61. Crystal structure of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, C10H16
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