Startseite Naturwissenschaften Crystal structure of (E)-2-(anthracen-9-ylmethylene)hydrazine-1-carbothioamide, C16H13N3S
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Crystal structure of (E)-2-(anthracen-9-ylmethylene)hydrazine-1-carbothioamide, C16H13N3S

  • Chao Liu EMAIL logo
Veröffentlicht/Copyright: 7. Februar 2018

Abstract

C16H13N3S, monoclinic, P21/c (no. 14), a = 19.0479(17) Å, b = 4.7282(4) Å, c = 16.7554(15) Å, β = 114.309(1)°, V = 1375.2(2) Å3, Z = 4, Rgt(F) = 0.0412, wRref(F2) = 0.1436, T = 293(2) K.

CCDC no.: 763346

The asymmetric unit of the title 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:Brown block
Size:0.25 × 0.23 × 0.20 mm
Wavelength:Mo radiation (0.71073 Å)
μ:0.23 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:25.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:6869, 2441, 0.033
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1724
N(param)refined:181
Programs:Bruker programs [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
S10.46809(4)0.11323(17)0.85501(5)0.0643(3)
N10.57922(14)0.3045(6)1.00050(14)0.0786(9)
H1A0.61970.40481.02810.094*
H1B0.55940.20641.02920.094*
N20.58195(11)0.4597(5)0.87381(13)0.0504(6)
H20.56150.47470.81770.061*
N30.64992(11)0.5984(5)0.92255(13)0.0487(6)
C10.54755(13)0.3010(6)0.91403(16)0.0497(7)
C20.67894(13)0.7378(5)0.87853(16)0.0433(6)
H2A0.65030.74910.81830.052*
C30.75326(12)0.8814(5)0.91456(14)0.0365(5)
C40.81327(13)0.8102(5)0.99696(14)0.0368(5)
C50.80709(14)0.5985(5)1.05470(16)0.0442(6)
H50.76080.50221.03930.053*
C60.86704(15)0.5349(6)1.13121(16)0.0492(6)
H60.86110.39421.16670.059*
C70.93798(15)0.6756(6)1.15832(17)0.0529(7)
H70.97820.63171.21170.063*
C80.94707(14)0.8762(5)1.10576(16)0.0496(7)
H80.99400.96951.12350.060*
C90.88646(13)0.9474(5)1.02407(15)0.0394(6)
C100.89780(14)1.1483(5)0.96999(15)0.0430(6)
H100.94541.23760.98870.052*
C110.84073(13)1.2203(5)0.88915(15)0.0395(6)
C120.85456(15)1.4245(5)0.83458(18)0.0501(7)
H120.90241.51230.85400.060*
C130.79941(16)1.4925(6)0.75531(18)0.0554(7)
H130.80931.62620.72050.066*
C140.72702(16)1.3602(6)0.72562(18)0.0551(7)
H140.68931.40660.67080.066*
C150.71105(14)1.1664(5)0.77536(16)0.0493(7)
H150.66241.08450.75400.059*
C160.76701(13)1.0842(5)0.85986(15)0.0377(6)

Source of material

The title compound was synthesized by the reaction of hydrazinecarbothioamide (1 mmol, 91.1 mg) with anthracene-9-carbaldehyde (1 mmol, 206.2 mg) in ethanol (20 mL) containing a few droups of glacial acetic acid under reflux conditions (353 K) for 5 h. When cooled to room temperature, the solution was filtrated and then stand at room temperature. After about 4 days, brown, block-shaped crystals suitable for X-ray diffraction study were obtained.

Experimental details

All H atoms were placed in calculated positions (C—H = 0.93 Å, N—H = 0.86 Å) and refined as riding atoms. The Uiso values were constrained to be 1.2Ueq of the carrier atom for all H atoms.

Discussion

Synthesis of Schiff-bases and their derivatives have been investigated for many years due to their higher bioactivity and applications in metal coordination chemistry. Among the Schiff bases, thiosemicarbazones containing S, N donor ligands are of particular interest because of their coordination chemistry [3], [4], [5], [6], [7] and broad spectrum of biological activities [8], [9], [10], [11].

In order to search for new thiosemicarbazones with higher bioactivity, the title compound was synthesized and its crystal structure is reported here.

The C = N bond length in the molecule of 1.273(3) Å (C9 = N2) shows a typical double-bond character. The C = N—N angle of 115.4(2)° (C2 = N3—N2) is much smaller than the ideal value of 120° expected for sp2 N atoms. This is probably a consequence of repulsion between the nitrogen lone pairs and the adjacent N bonds. The dihedral angle formed by the anthracenyl moiety and the mean plane of thiosemicarbazone unit is 26°. In the crystal structure, A dimer structure is formed by the N—H⋯S hydrogen bonds.

Acknowledgements

This work was financial supported by Changsha Enviromental Protection College.

References

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Received: 2017-10-31
Accepted: 2018-1-23
Published Online: 2018-2-7
Published in Print: 2018-3-28

©2018 Chao Liu, 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 and optical properties of diaqua-tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(p-pyridyl)imidazoline-1-oxyl 3-oxide-κN)praseodymium(III), C24H36N9O15Pr
  3. Crystal structure of dimethanol-bis(μ2-methanol-κ2O:O)-bis{3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}dimanganese(II), C38H38Mn2N2O14
  4. Crystal structure of catena-poly[diaqua-bis(μ2-2-(2-((2,6-dichlorophenyl)amino)phenyl)acetato-κ3O,O′:O′)calcium(II)], C56H48N4Ca2Cl8O12
  5. Crystal structure of catena-poly[triaqua-(isophthalato-κO)-(μ2-1,6-di(1H-imidazol-1-yl)hexane-κ2N:N′)]nickel(II), C20H28N4NiO7
  6. Crystal structure of cyclo[hexaqua-bis[1-[(2-ethyl-1H-imidazol-1-yl) methyl]-1H-benzotriazole-κ2N:N′]-bis(sulfato-κ1O)dicadmium(II)] monohydrate, C24H42Cd2N10O16S2
  7. Crystal Structure of bis(2-fluorbenzoato-κO)-bis(1,10-phenanthroline-κ2N,N′)manganese(II) dihydrate, C38H28F2MnN4O6
  8. Crystal structure of tetrapropylammonium 5-hydroxyisophthalate tetrahydrate, C20H41NO9
  9. Crystal structural of 2-amino-4-(3-bromophenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran, C18H17BrN2O2
  10. Crystal structural of 2-amino-4-(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C17H16N2O3
  11. Crystal structure of catena-poly[aqua(μ2-1,3-bis(1H-benzo[d]imidazol-1-yl)propane-κ2N:N′)-(μ2-5-(tert-butyl)isophthalate-κ3O,O′:O′′)nickel(II)], C29H30N4NiO5
  12. Crystal structure of catena-poly[(μ2-dicyanamido-κ2N:N′)-(μ2-2-(pyridin-2-yl)ethan-1-olato-κ3N,O:O′)copper(II)], C9H8CuN4O
  13. Crystal structure of bis(5,5′-((butane-1,4-diylbis(azanylylidene))bis(methanylylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido-k4N,N′,N′′,N′′′)copper(II), C24H32CuN4O4
  14. The crystal structure of the formamide solvate of (17b)-estra-1,3,5(10)-triene-3,17diol, C19H27NO3
  15. Crystal structure of catena-poly[diaqua-bis(μ2-1H-benzo[d]imidazole-5-carboxylato-κ2N:O)nickel(II)] dihydrate, C16H18N4NiO8
  16. Crystal structure of dibromido[(1,2-bis(diisopropylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]nickel(II), C14H38B10NiBr2P2
  17. The crystal structure of catena-poly[aquachlorido(3,3′-([4,4′-bipyridine]-1,1′-diium-1,1′-diylbis(methylene))dibenzoato-κ2O:O′)copper(II)] chloride dihydrate, C26H26Cl2CuN2O7
  18. The crystal structure of N′-(2-nitrobenzylidene)-2-phenylacetohydrazide, C15H13N3O3
  19. Crystal structure of dichlorido bis[1-[(2-methyl-1H-benzoimidazol-1-yl)methyl]-1H-benzotriazole-κ1N]cadmium(II), C30H26CdCl2N10
  20. Crystal structure of aqua-bis(3-(2-pyridyl)-5-(4-pyridyl)-1H-1,2,4-triazole-κ2N,N′)copper(II) sulfate tetrahydrate, C24H28CuN10O9S
  21. Crystal structure of dibromido-carbonyl-(η6-p-cymene)osmium(II), C11H14Br2OOs
  22. Crystal structure of catena-poly[chlorido-(μ2-chlorido)-bis(imidazole-κN)copper(II)] C6H8Cl2CuN4
  23. Crystal structure of [(1,2-bis(dicyclohexylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]dibromidonickel(II)), C26H54B10NiBr2P2
  24. Crystal structure of dichlorido[1,1′-bis(diphenylphosphanyl)ferrocene-κ2P,P′]zinc(II), C34H28FeCl2P2Zn
  25. Crystal structure of tris(μ2-2-(pyridin-2-yl)ethan-1-olato-κ3N,O:O)-trithiocyanato-κN-dicobalt(III), C24H24Co2N6O3S3
  26. The crystal structure of diaqua-2,2′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))diphenolato-κ4N,N′,O,O′)manganese(III) perchlorate, C20H24MnClN2O4
  27. Crystal structure of bis(μ3-chlorido)-bis(μ2-chlorido)-tetrakis(μ2-2,6-bis (diphenylmethyl)-4-t-butylphenolato)tetralithium(I)dicobalt(II) toluene solvate, C75.5H70Cl2CoLi2O2
  28. The crystal structure of hexaaqua-bis(μ2-3-(3-(pyridin-4-yl)-1,2,4-oxadiazol-5-yl)propanoato-κ2O:O′)-tetrakis(3-(3-(pyridin-4-yl)-1,2,4-oxadiazol-5-yl)propanoato-κO)dierbium(III) octahydrate, C60H76N18O32Er2
  29. Crystal structure of dimethylammonium bis(naphthalene-2,3-diolato)borate, C22H20BNO4
  30. Crystal structure of 2-amino-4-(4-nitro-phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C18H17N3O4
  31. The crystal structure of (E)-4-chloro-2-(((5-methylpyridin-2-yl)imino)methyl)phenol, C13H11ClN2O
  32. Crystal structure of bis(N,N,N-trimethylbutanaminium) poly[heptaselenidotristannate(IV)], C14H36N2Se7Sn3
  33. The crystal structure of N-((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)-4-methylbenzenesulfonamide, C28H35N3S
  34. Crystal structure of 2-(4-chlorophenyl)-2,3-dihydro-1H-perimidine, C17H13Cl1N2
  35. The Crystal structure of 2-iodo-1-(p-tolyl)propan-1-one, C10H11IO
  36. Crystal structure of ethyl 1-(4-bromobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C19H17BrN2O2
  37. Crystal structure of ethyl 1-(4-fluorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C19H17FN2O2
  38. Crystal structure of catena-poly[diaqua-(μ2-2,5-dihydroxyterephthalato-κ4O,O′:O′′,O′′′)cadmium(II)], C8H8O8Cd
  39. Crystal structure of tetraaqua-bis[6-(1H-imidazol-1-yl-κN)nicotinato]zinc(II), C18H20N6O8Zn
  40. Crystal structure of dichlorido-bis(N-phenyl-2-(quinolin-8-yloxy)acetamide-κ2N,O) – acetone (2/1), C35.5H31N4O4.5Cl2Cu
  41. Crystal Structure of ethyl (E)-3,4-dimethyl-5-((2-(4-methylbenzoyl)hydrazono)methyl)-1H-pyrrole-2-carboxylate — water — ethanol (1/1/1), C20H29N3O5
  42. Crystal structure of 5-((4-(1H-benzo[d]imidazol-2-yl)-2-methoxyphenoxy)methyl)-2-chlorothiazole - trichloromethane - methanol (1/1/1), C20H19Cl4N3O3S
  43. The crystal structure of a matrine derivative: 41S,7aS,12S,13aR,13bR)-12-(4-methylpiperazin-1-yl)dodecahydro-1H,5H,10H-dipyrido[2,1-f:3′,2′,1′-ij][1,6]naphthyridin-10-one, C20H34N4O
  44. Crystal structure of cesium beryllophosphate, Be3Cs2P4O14
  45. Crystal Structure of 3-((3-hydroxybenzyl)ammonio)-3-phenylpropanoate, C16H17NO3
  46. Crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride — 4-hydroxy-3-methoxybenzoic acid — water (2/1/5), C48H54N2Cl2O17
  47. The crystal structure of (1R, 2R)-N1,N2-diferrocenyl-1,2-cyclohexanedicarboxamide, C28H30Fe2N2O2
  48. Crystal structure of N-(2-methylphenyl)ethoxycarbothioamide, C10H13NOS
  49. Crystal Structure of ethyl (E)-2,4-dimethyl-5-((2-tosylhydrazono)methyl)-1H-pyrrole-3-carboxylate monohydrate, C17H23N3O5
  50. Crystal structure of Diiodo-(N′-((quinolin-8-yl)methylene)isonicotinohydrazide κ3N,N′,O)cadium(II) – dimethylformamide (1/1), C19H19N5O2CdI2
  51. Crystal structure of dinitrato-(N′-((quinolin-8-yl)methylene)isonicotinohydrazide κ3-N,N′,O)copper(II), C16H12N6O7Cu
  52. Crystal structure of benzoato-κO-bis(1,3,5-triaza-7-phosphaadamantane-κP)silver(I) monohydrate C19H31AgN6O3P2
  53. Crystal structure of (E)-2-(anthracen-9-ylmethylene)hydrazine-1-carbothioamide, C16H13N3S
  54. The crystal structure of 8-chloro-7-ethyl-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione, C9H11ClN4O2
  55. Crystal structure of {5,5′-((propane-1,3-diylbis(azanylylidene))bis(methanylylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido)-κ4N,N′,N′′,N′′′}zinc(II), C23H30N4O4Cu
  56. Crystal structure of bis(4-dimethylamino-pyridin-1-ium)tetrafluorosuccinate, C18H22F4N4O4
  57. Crystal structure of dimethyl 3,9-dibenzyl-6,12-dicyclohexyl-3,9-diazahexacyclo [6.4.0.02,7.04,11.05,10]-dodecane-1,11-dicarboxylate, C40H50N2O4
  58. Crystal structure of diethyl 3,9-diphenyl-6,12-bis(3-methoxyphenyl)-3,9-diazahexacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,11-dicarboxylate, C42H42N2O6
  59. Crystal structure of bis(acetato-κO)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)nickel(II), C18H22N4NiO6
  60. Crystal structure of (N-(3-ethoxy-2-oxidobenzylidene)-4-fluorobenzohydrazonato-κ3N,O,O′)-diphenyltin(IV), C28H23FN2O3Sn
  61. Crystal structure of {N-(3-ethoxy-2-oxidobenzylidene)-4-fluorobenzohydrazonato-κ3O,N,O′}dimethyltin(IV), C18H19FN2O3Sn
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