Startseite Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S
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Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S

  • Weiping Liu EMAIL logo
Veröffentlicht/Copyright: 5. September 2018

Abstract

C14H11F2N3S, monoclinic, C2/c (no. 15), a = 18.5399(19) Å, b = 9.5907(10) Å, c = 16.8149(17) Å, β = 111.307(2)°, V = 2785.5(5) Å3, Z = 8, Rgt(F) = 0.0390, wRref(F2) = 0.1317, T = 293(2) K.

CCDC no.: 1860150

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:

Crystal collection and handling.

Crystal:Block, colorless
Size:0.25 × 0.23 × 0.20 mm
Wavelength:Mo Kαradiation (λ = 0.71073 Å)
μ:0.247 mm−1
Diffractometer, scan mode:Bruker APEX-II CCD, Φ and ω-scans
θmax, completeness:25.00°, 100%
N(hkl)measured, N(hkl)unique, Rint:7800, 2458, 0.0242
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 2186
N(param)refined:181
Programs:Bruker [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
S10.40582(2)0.97556(5)1.12682(3)0.0512(2)
F10.74160(9)0.39767(16)0.89571(11)0.0984(5)
F20.20944(7)0.69860(18)0.68459(9)0.0920(5)
N10.54461(8)0.86275(18)1.16615(10)0.0587(4)
H1A0.57820.81501.15350.070
H1B0.55610.89551.21690.070
N20.46162(8)0.83120(16)1.02977(8)0.0457(4)
H2A0.41750.84370.98940.055
N30.51857(7)0.75549(14)1.01526(8)0.0423(3)
C10.56551(9)0.61877(15)0.92831(10)0.0377(4)
C20.64247(9)0.65024(18)0.97601(11)0.0440(4)
H20.65390.72301.01520.053
C30.70198(10)0.5754(2)0.96604(13)0.0539(5)
H30.75330.59580.99850.065
C40.68358(12)0.4702(2)0.90702(14)0.0604(5)
C50.60895(13)0.4351(2)0.85866(14)0.0625(5)
H50.59850.36220.81970.075
C60.54932(11)0.51068(18)0.86910(12)0.0497(4)
H60.49820.48910.83640.060
C70.42325(9)0.69630(15)0.87373(10)0.0364(4)
C80.36178(11)0.6305(2)0.88556(12)0.0584(5)
H80.36920.58590.93710.070
C90.28938(11)0.6299(2)0.82191(14)0.0657(6)
H90.24790.58500.82960.079
C100.28025(10)0.6968(2)0.74770(12)0.0535(5)
C110.33862(10)0.7645(2)0.73339(11)0.0526(4)
H110.33020.81000.68190.063
C120.41110(9)0.76395(18)0.79759(10)0.0444(4)
H120.45200.80970.78930.053
C130.50189(9)0.69505(15)0.94241(10)0.0374(4)
C140.47545(9)0.88571(16)1.10779(10)0.0413(4)

Source of material

The title compound was synthesized by the reaction of hydrazinecarbothioamide (1 mmol, 91.1 mg) with bis(4-fluorophenyl)methanone (1 mmol, 218.2 mg) in ethanol (15 mL) containing catalytic amounts of glacial acetic acid under reflux conditions (353 K) for 3 h. When cooled to room temperature, the solution was filtrated and then stand at room temperature. After about 3 days, colourless block crystals were obtained.

Experimental details

All H atoms were geometrically placed in calculated positions (C—H = 0.93 Å, N—H = 0.86 Å ) and refined as riding atoms, with Uiso = 1.2Ueq of the parent atoms.

Discussion

As one important kind of Schiff-bases, thiosemicarbazones constitute an important class of N, S donor ligands and have gained more and more attention in recent years not only because of their chemistry, but also their biological activities [3], [4], [5], [6], [7], [8], [9], [10], [11], [12], [13], [14]. Compared with the traditional thiosemicarbazones, the fluorine-containing thiosemicarbazones may exhibit other biological activities because of the inclusion of fluorine atoms in the molecules often has a great influence on their physical and chemical properties. But the fluorine-containing thiosemicarbazones are not well studied [11], [15]. In order to search for new thiosemicarbazones containing fluorine atoms, the title compound was synthesized.

There is one title molecule in the asymmetric unit. The C13 = N3 bond distance in the molecule of 1.287(2) Å exhibits the expected value for a double-bond. The C14 = S1 bond distance in the molecule is 1.6768(16) Å, which is between the typical C—S single-bond (1.82 Å) and the typical C = S double-bond (1.56 Å), thus reflecting a partial double bond character. The C = N—N angle of 118.20(12)° (C13 = N3—N2) is smaller than the expected 120°. The dihedral angle formed by the two phenyl rings is 80.6°. In the crystal structure, a dimer structure is formed by the N—H⋯S hydrogen bonds. The adjacent dimers are further linked into infinite chains by weak C—H⋯S hydrogen bonds. In addition, very weak N—H⋯F hydrogen bonds link these chains into layers.

Acknowledgements

This work was financial supported by Changsha Environmental Protection College.

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Received: 2018-06-23
Accepted: 2018-08-03
Published Online: 2018-09-05
Published in Print: 2018-11-27

©2018 Weiping 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
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  3. Crystal structure of diaqua-bis(2-bromo-4-chloro-6-formylphenolato-κ2O,O′)cobalt(II), C16H16Cl2CrN3O7
  4. Crystal structure of catena-poly[(μ2-1-(4-(1H-pyrazol-1-yl)phenyl)ethan-1-one-κ2N:O)-bis(1,1,1-trifluoro-4-oxo-4-(thiophen-2-yl)but-2-en-2-olato-κ2O,O′)copper(II)], C27H18CuF6N2O5S2
  5. Crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C18H15F2NO5
  6. Crystal structure of 5,5′-dimethoxy-2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]diphenol, C20H24N2O6
  7. Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H14Cl2N2O2
  8. Crystal structure of 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine - trichloromethane (1/2), C98H84Cl6N8O8
  9. Crystal structure of methyl 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate, C24H21N3O5
  10. Crystal structure of catena-poly[(μ2-3,3′-thiodipropionato-κ2O:O′)-(bipyridine-κ2N,N′)copper(II)] C16H16CuN2O4S
  11. Crystal structure of [4-chloro-2-(((2-((3-ethoxy-2-oxidobenzylidene)amino)phenyl)imino)(phenyl)methyl)phenolato-κ4N,N′,O,O′}nickel(II) - ethyl acetate (1/1), C32H29ClN2NiO5
  12. Crystal structure of (4-(4-chlorophenyl)-5-ethyl-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, C29H52Cl2N4NiO9
  13. Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C20H21NO5
  14. Structure and photochromism of 1,2-bis[2-methyl-5-(3-quinolyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C33H20F6N2S2
  15. Crystal structure of catena-poly[diaqua-bis(μ2-3,5-di(1H-1,2,4-triazol-1-yl)benzoate-κ2N:N′)cobalt(II))] 2.5 hydrate, C22H23CoN12O8.50
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  19. The crystal structure of 2-hydroxy-4-((2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy)-3,6-dimethylbenzoic acid–methanol (1/1), C20H24O8
  20. Crystal structure of guanidinium tetrapropylammonium bis(hydrogencarbonate) dihydrate, C15H40N4O8
  21. Crystal structure of (Z)-2-bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one, C23H27BrO2
  22. Crystal structure of 2-(4-(4H-1,2,4-triazol-4-yl)phenyl)acetic acid, C10H9N3O4
  23. Crystal structure of 4,4′-(1,4-phenylene)bis(1H-imidazol-3-ium)bis(2-carboxybenzoate), C30H26N4O8
  24. Crystal structure of 4,4′-(4,10-diphenyl-4,10-dihydropyreno[4,5-d:9,10-d′]diimidazole-5,11-diyl)bis(N,N-diphenylaniline), C66H44N6
  25. Crystal structure of catena-poly[diaqua-bis(μ2-5-(3-(1H-imidazol-5-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)], C20H18CoN12O2
  26. Crystal structure of 1,3-dimethyl-2-(p-tolyl)-1H-perimidin-3-ium iodide 1.5 hydrate, C20H22IN2O1.5
  27. Crystal structure of 2-(4-methoxyphenyl)chromane, C16H16O2
  28. Crystal structure of poly[(μ2-2-carboxy-5-nitroisophthalato-κ2O:O′)-(μ2-4-((1H-imidazol-1-yl)methyl)pyridine-κ2N:N′)zinc(II)], C18H12N4O8Zn
  29. Crystal structure of bis(1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)tetraiodidodicadmium(II), [Cd2(C13H15N5)2I4]
  30. Crystal structure of tetramethylammonium bis(acetato-κ1O)-tetrakis(μ3-3-((hydroxyimino)methyl)-5-methoxy-2-oxidobenzoate-κ5O,O′:O′,N:O′′)tetrazinc(II) — N,N′-dimethylformamide — water (1/2/2), C62H96Zn4N10O28
  31. Crystal structure of poly[(μ4-5-tert-butylisophthalato-κ4O:O′:O′′:O′′′)-(1,3-dimethyl-2-imidazolidinone-κO)zinc(II)] C17H22N2O5Zn
  32. Crystal structure of [tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′]-[(pyridine-2,6-dicarboxylato-κ2O,N)]cadmium(II)–methanol (1:3) C34H36CdN8O7
  33. The crystal structure of bis(1H-benzo[d]imidazol-2-amine-κN)-diiodidocadmium(II), C14H14CdI2N6
  34. Crystal structure of tetrakis(1H-benzimidazol-2-amine)-κN)-bis(μ2-sulfonato-κ2O:O′)dizinc(II) - methanol (1/1), C30H36N12O10S2Zn2
  35. Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO
  36. Crystal structure of dimethyl 4,4′-oxydibenzoate, C16H14O5
  37. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-3-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)zinc(II)], C17H16I2N4OZn
  38. Crystal structure of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile, C26H18F2N2O3S
  39. Crystal structure of bis(acetato-κ1O)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)zinc(II), C18H22N4O6Zn
  40. The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
  41. Crystal stucture of 2-(tert-butyl)-6-(hydroxymethyl)-4-methylphenol, C12H18O2
  42. Crystal structure of catena-poly[(2-(5-chloroquinolin-8-yloxy)-1-(pyrrolidin-1-yl)ethan-1-one-κ3N,O,O′)-(dinitrato-κ2O,O′)mercury(II)], C15H15N4O8ClHg
  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
  44. The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
  45. Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
  46. The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
  47. Crystal structure of 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
  48. Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S
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