Startseite Crystal structure of 1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea, C17H21ClN2S
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Crystal structure of 1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea, C17H21ClN2S

  • Fatmah A. M. Al-Omary , Lamees S. Al-Rasheed , Hazem A. Ghabbour und Ali A. El-Emam EMAIL logo
Veröffentlicht/Copyright: 1. Oktober 2016

Abstract

C17H21ClN2S, orthorhombic, Pca21 (no. 29), a = 25.4796(11) Å, b = 6.7503(3) Å, c = 18.9971(9) Å, V = 3267.4(3) Å3, Z = 8, Rgt(F) = 0.045, wRref(F2) = 0.106, T = 293(2).

CCDC no.:: 1482683

The asymmetric unit of the title crystal 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:Colourless plate Size 0.57 × 0.13 × 0.07 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:32.1 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:125°, >99%
N(hkl)measured, N(hkl)unique, Rint:10037, 4231, 0.075
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3598
N(param)refined:395
Programs:SHELX [23, 25], Bruker programs [24]
Table 2

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

AtomxyzUiso*/Ueq
Cl1A0.49654(5)0.5878(3)0.32784(14)0.1091(7)
S1A0.68656(4)0.67589(18)0.42702(5)0.0419(3)
N1A0.76395(12)0.6589(6)0.33097(17)0.0412(9)
N2A0.69442(13)0.4632(6)0.31012(18)0.0408(8)
C1A0.80128(14)0.8022(7)0.36347(18)0.0352(9)
C2A0.84834(16)0.8198(9)0.3131(2)0.0592(14)
H2AA0.86460.69100.30700.071*
H2AB0.83640.86530.26740.071*
C3A0.88835(17)0.9656(10)0.3428(2)0.0600(15)
H3AA0.91810.97520.31030.072*
C4A0.8645(2)1.1674(10)0.3520(3)0.0713(17)
H4AA0.85301.21840.30690.086*
H4AB0.89031.25790.37130.086*
C5A0.8180(2)1.1508(8)0.4018(4)0.0676(17)
H5AA0.80191.28150.40770.081*
C6A0.77735(16)1.0064(7)0.3710(3)0.0534(12)
H6AA0.74700.99980.40180.064*
H6AB0.76581.05360.32540.064*
C7A0.82129(17)0.7287(7)0.4339(2)0.0452(10)
H7AA0.83760.59990.42800.054*
H7AB0.79210.71440.46630.054*
C8A0.86106(18)0.8738(8)0.4639(2)0.0527(13)
H8AA0.87320.82540.50980.063*
C9A0.8362(2)1.0737(9)0.4731(3)0.0689(16)
H9AA0.86141.16500.49350.083*
H9AB0.80651.06370.50490.083*
C10A0.90804(16)0.8919(9)0.4140(3)0.0556(13)
H10A0.93350.98440.43310.067*
H10B0.92500.76410.40860.067*
C11A0.71667(14)0.5983(6)0.35278(18)0.0329(9)
C12A0.64287(14)0.3841(7)0.3155(2)0.0376(9)
C13A0.59943(15)0.5096(8)0.3215(2)0.0443(10)
H13A0.60390.64600.32500.053*
C14A0.55054(16)0.4290(8)0.3221(3)0.0520(12)
C15A0.54230(17)0.2287(8)0.3175(3)0.0567(13)
H15A0.50840.17750.31780.068*
C16A0.5843(2)0.1070(8)0.3125(3)0.0606(13)
H16A0.5793−0.02920.30930.073*
C17A0.63533(17)0.1846(7)0.3119(3)0.0499(11)
H17A0.66400.09990.30920.060*
Cl1B0.92718(5)0.3868(3)0.63196(9)0.0822(5)
S1B0.71517(4)0.29413(18)0.69106(5)0.0457(3)
N1B0.66477(13)0.3483(6)0.56782(19)0.0426(9)
N2B0.73437(14)0.5480(7)0.5876(2)0.0490(10)
C1B0.62103(13)0.2054(6)0.5755(2)0.0341(9)
C2B0.58598(16)0.2555(8)0.6384(2)0.0480(11)
H2BA0.57300.39010.63430.058*
H2BB0.60580.24490.68180.058*
C3B0.53941(17)0.1074(9)0.6392(3)0.0601(15)
H3BA0.51690.13540.67980.072*
C4B0.50751(16)0.1298(9)0.5716(3)0.0582(13)
H4BA0.49440.26420.56770.070*
H4BB0.47770.04020.57240.070*
C5B0.54266(16)0.0819(10)0.5086(2)0.0590(15)
H5BA0.52250.09610.46500.071*
C6B0.58902(18)0.2260(10)0.5076(2)0.0586(14)
H6BA0.57620.36070.50330.070*
H6BB0.61120.19810.46740.070*
C7B0.5604(2)−0.1019(9)0.6448(3)0.0701(17)
H7BA0.5809−0.11550.68760.084*
H7BB0.5315−0.19490.64700.084*
C8B0.59439(18)−0.1473(8)0.5815(4)0.0646(15)
H8BA0.6075−0.28350.58510.078*
C9B0.64090(16)−0.0040(7)0.5809(3)0.0534(12)
H9BA0.6613−0.01960.62370.064*
H9BB0.6635−0.03320.54110.064*
C10B0.5625(2)−0.1261(10)0.5146(3)0.0749(19)
H10C0.5842−0.15760.47420.090*
H10D0.5332−0.21760.51550.090*
C11B0.70381(14)0.3980(7)0.61204(19)0.0354(9)
C12B0.78326(15)0.6087(7)0.6165(2)0.0384(10)
C13B0.82562(16)0.4809(8)0.6141(2)0.0455(10)
H13B0.82170.35210.59750.055*
C14B0.87362(15)0.5480(8)0.6368(2)0.0486(12)
C15B0.88093(18)0.7342(9)0.6609(2)0.0537(13)
H15B0.91390.77640.67550.064*
C16B0.8381(2)0.8615(8)0.6633(2)0.0549(13)
H16B0.84230.98990.68010.066*
C17B0.78942(17)0.7983(7)0.6410(2)0.0462(11)
H17B0.76090.88390.64260.055*
H1NB0.6668(15)0.419(7)0.530(2)0.029(11)*
H2NB0.724(2)0.612(8)0.554(3)0.056(16)*
H2NA0.7105(17)0.429(7)0.270(3)0.042(12)*
H1NA0.7738(17)0.600(7)0.294(3)0.040(12)*

Source of material

3-Chlorophenyl isothiocyanate (1.70 g, 0.01 mol) was added to a solution of 1-adamantylamine (1.51 g, 0.01 mol), in ethanol (15 mL). The mixture was heated under reflux for 3 h. On cooling, the precipitated crude product was filtered, dried and crystallized from ethanol to yield 2.79 g (87%) of the title compound (C17H21ClN2S) as transparent plate crystals. M.P.: 444–446 K. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in ethanol:chloroform (1:1) at room temperature. 1H NMR (CDCl3, 700.17 MHz): δ 1.60–1.72 (m, 6H, adamantane-H), 2.08.2.10 (s, 3H, adamantane-H), 2.14 (s, 6H, adamantane-H), 6.02 (s, 1H, NH), 7.14 (s, 1H, Ar—H), 7.24–7.35 (m, 3H, Ar—H), 7.7 (s, 1H, NH). 13C NMR (CDCl3, 176.08 MHz): δ 29.54, 36.28, 41.29, 54.96 (adamantane-C), 122.71, 124.74, 126.74, 130.92, 135.51, 138.09 (Ar—C), 178.39 (C = S). ESI-MS m/z: 319.2 (M—H, 100%), 321.2 (M + 2-H, 33%).

Experimental details

Carbon-bound hydrogen atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The Flack parameter was refined to −0.002(19).

Discussion

Thiourea derivatives were reported to possess diverse biological properties such as antitumor [1], antiviral [2], antimalarial [3] and antimicrobial [4] activities. In addition, adamantanyl moiety represents the major pharmacophore of various antiviral drugs as amantadine , [5], [6], [7], rimantadine [8, 9] and tromantadine [10]. Moreover, several adamantane-based drugs are currently utilized as important therapies against malaria infections [11], central nervous disorders , [12], [13], [14], hyperglycaemia [15] and drug-resistant TB strain infections [16]. As a part of our current research interest in the chemotherapeutic properties of adamantane derivatives , [17], [18], [19] and the molecular structural of adamantyl thiourea analogues , [20], [21], [22], we report herein the synthesis and crystal title structure.

The asymmetric unit cell of the title structure contains two independent molecules. All bond lengths and angles are in the expected ranges. The molecules are packed in the crystal structure via five intermolecular hydrogen bonds, N1B—H1NB⋯S1A, N2B—H2NB⋯S1A, N2A—H2NA⋯S1Bi, N1A—H1NA⋯S1Bi and C4A—H4AA⋯S1Bii. The H⋯A distances are 2.66(4), 2.63(6), 2.58(5), 2.86(5) and 2.85 Å, respectively and the angles are 169(3), 157(5), 157(4), 160 and 159°, respectively. Symmetry codes: (i) − x + 3/2, y, z−1/2; (ii) − x + 3/2, y + 1, z−1/2.

Acknowledgements:

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. PRG-1436-23.

References

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Received: 2016-5-31
Accepted: 2016-8-24
Published Online: 2016-10-1
Published in Print: 2017-1-1

©2016 Fatmah A. M. Al-Omary et al., published by De Gruyter.

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

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  32. Crystal structure of dibromido-bis[μ-1-[(2-methyl-1H-benzoimidazol-1-yl)methyl]-1H-benzotriazole-κN]mercury(II), C30H26Br2HgN10
  33. Crystal structure of bis(μ-nitrato-κ2O:O)-bis[1,2-bis(diphenylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]disilver(I) dicloromethane monosolvate, C54H64B20Cl4O6P4Ag2
  34. Crystal structure of dinuclear dichloridobis(dimethylformamide-kO)bis[μ2-3-(2-oxyphenyl)-5-(pyrazin-2-yl)-1,2,4-triazol-1ido-κ4-O,N:N′,N′′(2)]diiron(III) dimethylformamide (1/1), C36H42Cl2Fe2N14O6
  35. Crystal structure of diaqua-dinitrato-κO-bis(4-(1H-pyrazol-3-yl)pyridine-κN)manganese(II), C16H18MnN8O8
  36. Crystal structure of (Z)-6-methoxy-2-(2,2,2-trifluoro-1-hydroxyethylidene)-2,3-dihydro-1H-inden-1-one, C12H6F6O3
  37. Crystal Structure of 4-(2-chloroacetamido)pyridinium chloride monohydrate, C7H10Cl2N2O2
  38. Crystal structure of 2-amino-4-(4-chloro-phenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H13ClN2O2
  39. Crystal structure of (E)-1-(2-(thiophen-2-ylmethylene)hydrazinyl)phthalazine hydrochloride–ethanol (1/1), C15H17ClN4OS
  40. Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C9H12BrN3O3
  41. Crystal structure of 3-(2-(4-chlorophenyl)-3-hydroxy-3,3-diphenylpropyl)-1,1-dimethylurea, C24H25ClN2O2
  42. Crystal structure of 3-(4-chlorophenyl)-1,1-dimethylthiourea, C9H11ClN2S
  43. Crystal structure of 2-amino-4-(4-bromo-phenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C16H11BrN2O3
  44. Crystal structure of 4-(3,4-dimethyl-phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester, C21H25NO3
  45. Crystal structure of (E)-2-({4-hydroxy-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]phenyl} methylidene)-1-indanone, C23H26N2O3
  46. Crystal structure of tripropylammonium 2′-carboxy-[1,1′-biphenyl]-2-carboxylate – [1,1′-biphenyl]-2,2′-dicarboxylic acid (2/1), C60H72N2O12
  47. Crystal structure of catena-poly-{aqua-[μ2-1,2-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′]-[μ2-4,4′-(dimethylsilanediyl)dibenzato-κ3O,O′:O′]nickel(II)}, C30H30N4NiO5Si
  48. The crystal structure of 1-(4-bromophenyl)-2-(4-(4-fluorophenyl)piperazin-1-yl)ethanol, C18H20BrFN2O1
  49. Crystal structure of trimethylammonium 4-((4-carboxyphenyl)sulfonyl)benzoate, C17H19NO6S
  50. Crystal structure of syn-2,4-di-o-tolylpentane-2,4-diol, C19H24O2
  51. Crystal structure of 2-[3,5-bis(trifluoromethyl)benzylsulfanyl]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C15H7BrF6N2OS2
  52. Crystal structure of (E)-3-((naphthalen-1-ylimino)methyl)-4-nitrophenol, C17H12N2O3
  53. Crystal structure of 2-dichloromethyl-2-p-nitrophenyl-1,3-dioxolane, C10H9Cl2NO4
  54. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanopalladate(II), C14H24N8Pd2
  55. Crystal structure of 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic acid monohydrate, C5H7NO4S2
  56. Crystal structure of a P4-bridged (η5-pentamethyl-cyclopentadienyl)(η5-adamantylcyclopentadienyl) titanium(III)complex, C50H66P4Ti2
  57. Crystal structure of cis-bis(2,2′-bipyrimidine-κ2N,N′)bis(thiocyanato-κN)nickel(II), C18H12N10NiS2
  58. Crystal structure of cis-bis(2,2′-bipyridine-κ2N,N′)dibromidomanganese(II), C20H16Br2MnN4
  59. Crystal structure of cis-bis(2,2′-bipyridine-κ2N,N′)bis(thiocyanato-κN)nickel(II), C22H16N6NiS2
  60. Crystal structure of trans-dibromido(1,4,8,11-tetraazacyclotetradecane)nickel(II), C10H24Br2N4Ni
  61. Crystal structure of cis-tetrabromidobis(pyridine-κN)platinum(IV), C10H10Br4N2Pt
  62. Crystal structure of (E)-5-((4-chlorophenyl)diazenyl)-2-(5-(4-fluorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole, C23H17ClFN5S2
  63. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridocobaltate(II) monohydrate, C10H18Cl4CoN2O
Heruntergeladen am 19.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2016-0117/html
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