Home Physical Sciences Crystal structure of 5-(adamantan-1-yl)-3-[(4-chloroanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, C19H22ClN3OS
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Crystal structure of 5-(adamantan-1-yl)-3-[(4-chloroanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, C19H22ClN3OS

  • Monirah A. Al-Alshaikh , Hazem A. Ghabbour EMAIL logo , Abdul-Malek S. Al-Tamimi , Mohammed S.M. Abdelbaky , Santiago Garcia-Granda and Ali A. El-Emam
Published/Copyright: January 29, 2016

Abstract

C19H22ClN3OS, orthorhombic, P212121 (no. 19), a = 7.0418(2) Å, b = 10.8802(3) Å, c = 23.5506(6) Å, V = 1804.36(8) Å3, Z = 4, Rgt(F) = 0.0413, wRref(F2) = 0.1110, T = 100 K.

CCDC no.:: 1405608

The crystal structure is shown in the figure. Tables 13 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, prism, size 0.2231×0.5389×0.7274 mm
Wavelength:CuKα radiation (1.54184 Å)
μ:30.49 cm−1
Diffractometer, scan mode:Xcalibur, Ruby, Gemini, ω scans
2θmax:140.8°
N(hkl)measured, N(hkl)unique:15818, 3444
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3373
N(param)refined:231
Programs:CrysAlis [17], SHELX [18]
Table 2

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

AtomSitexyzUiso
H(9A)4a0.5080−0.05210.19010.031
H(9B)4a0.6646−0.04490.14270.031
H(15)4a−0.3588−0.10970.02160.037
H(10)4a0.8080−0.09950.23010.033
H(8A)4a0.45890.27150.21560.033
H(8B)4a0.38090.14270.23500.033
H(18)4a0.1008−0.32920.11890.041
H(4A)4a0.79170.16210.11100.036
H(4B)4a0.71320.28350.13860.036
H(13A)4a0.15140.0956−0.02900.036
H(13B)4a0.2343−0.0282−0.00620.036
H(7)4a0.60370.21540.30320.035
H(16)4a−0.4431−0.28220.07340.044
H(19)4a0.1838−0.15220.07100.038
H(5)4a1.01170.23590.17890.043
H(6A)4a0.79150.33470.24000.043
H(6B)4a0.92340.24730.27560.043
H(12A)4a1.05090.05150.23100.042
H(12B)4a0.99870.01940.16780.042
H(11A)4a0.80000.03950.30700.035
H(11B)4a0.5919−0.00030.29150.035
H(3)4a−0.133(4)0.032(3)−0.004(2)0.05(1)
Table 3

Atomic displacement parameters (Å2).

AtomSitexyzU11U22U33U12U13U23
S(1)4a0.08526(8)0.33243(6)0.03351(3)0.0228(3)0.0306(3)0.0473(3)0.0020(2)−0.0023(2)0.0118(3)
Cl(1)4a−0.2398(1)−0.45144(6)0.14068(3)0.0636(5)0.0355(3)0.0392(3)−0.0125(3)0.0101(3)0.0039(2)
O(1)4a0.3371(2)0.2459(2)0.10883(7)0.0238(8)0.0236(8)0.0351(9)0.0009(7)−0.0003(7)0.0015(7)
N(2)4a0.2306(3)0.1054(2)0.05303(8)0.0245(9)0.0250(9)0.0279(9)−0.0030(8)−0.0031(8)0.0042(7)
N(1)4a0.3609(3)0.0477(2)0.08851(8)0.0238(9)0.0243(9)0.0292(9)0.0000(8)0.0003(8)0.0044(8)
C(2)4a0.4201(3)0.1342(2)0.12104(9)0.019(1)0.023(1)0.030(1)−0.0006(9)0.0042(9)0.0033(8)
N(3)4a−0.0360(3)−0.0064(2)0.0103(1)0.026(1)0.028(1)0.043(1)0.0018(9)−0.0098(9)0.0059(9)
C(14)4a−0.0788(4)−0.1109(2)0.04094(9)0.029(1)0.028(1)0.028(1)0.000(1)−0.000(1)−0.0050(9)
C(1)4a0.2174(3)0.2252(2)0.0643(1)0.019(1)0.029(1)0.033(1)−0.0022(9)0.0034(9)0.0068(9)
C(9)4a0.6193(3)−0.0073(2)0.1775(1)0.025(1)0.021(1)0.033(1)0.0008(9)−0.0020(9)−0.0027(9)
C(15)4a−0.2665(4)−0.1524(2)0.0418(1)0.029(1)0.028(1)0.035(1)0.003(1)−0.001(1)−0.009(1)
C(10)4a0.7746(3)−0.0134(2)0.2231(1)0.025(1)0.024(1)0.033(1)0.0010(9)−0.002(1)−0.0005(9)
C(3)4a0.5669(3)0.1282(2)0.16640(9)0.019(1)0.021(1)0.031(1)−0.0024(9)0.0024(9)0.0003(8)
C(8)4a0.4931(3)0.1863(2)0.2221(1)0.024(1)0.024(1)0.035(1)0.0023(9)0.0016(9)−0.0016(9)
C(18)4a0.0083(4)−0.2835(2)0.1002(1)0.042(1)0.030(1)0.030(1)0.000(1)−0.002(1)0.000(1)
C(4)4a0.7451(3)0.1982(2)0.1460(1)0.023(1)0.033(1)0.035(1)−0.008(1)0.001(1)0.0067(9)
C(13)4a0.1510(4)0.0399(2)0.0031(1)0.031(1)0.031(1)0.030(1)−0.002(1)−0.0042(9)0.004(1)
C(7)4a0.6497(4)0.1787(2)0.2677(1)0.031(1)0.028(1)0.030(1)−0.002(1)−0.0008(9)−0.005(1)
C(17)4a−0.1787(4)−0.3207(2)0.1017(1)0.051(2)0.026(1)0.029(1)−0.006(1)0.009(1)0.000(1)
C(16)4a−0.3174(4)−0.2562(3)0.0725(1)0.032(1)0.036(1)0.040(1)−0.007(1)0.008(1)−0.011(1)
C(19)4a0.0581(4)−0.1785(2)0.0709(1)0.029(1)0.033(1)0.032(1)−0.000(1)−0.002(1)0.001(1)
C(5)4a0.8989(4)0.1911(3)0.1918(1)0.024(1)0.042(2)0.041(1)−0.014(1)−0.002(1)0.009(1)
C(6)4a0.8249(4)0.2494(3)0.2468(1)0.036(1)0.030(1)0.041(1)−0.014(1)−0.011(1)0.002(1)
C(12)4a0.9516(3)0.0563(3)0.2025(1)0.019(1)0.050(2)0.037(1)0.001(1)0.001(1)−0.001(1)
C(11)4a0.7023(3)0.0444(2)0.2781(1)0.027(1)0.030(1)0.030(1)−0.003(1)0.0000(9)−0.001(1)

Source of material

4-Chloroaniline (1.28 g, 0.01 mol) and 37% formaldehyde solution (1.5 mL) were added to a solution of 5-(1-adamantyl)-1,3,4-oxadiazoline-2-thione (2.36 g, 0.01 mol) in ethanol (15 mL), and the mixture was stirred at room temperature for 2 hours and allowed to stand overnight. The precipitated crude product was filtered, washed with cold ethanol, dried, and crystallized from ethanol to yield 3.46 g (92%) of the title compound. M.p. 450–452 K [9]. Colourless prismatic single crystals were obtained by slow evaporation of chloroform-ethanol solution (1:1) at room temperature. 1H NMR (CDCl3, 500.13 MHz): δ 1.68 (q, 6H, adamantane-CH2), 1.93 (s, 6H, adamantine-CH2), 2.07 (s, 3H, adamantane-CH), 5.06 (t, 1H, NH), 5.36 (d, 2H, CH2), 6.80 (d, 2H, Ar—H, J = 7.0 Hz), 7.14 (d, 2H, Ar—H, J = 7.0 Hz). 13C NMR (CDCl3, 125.76 MHz): δ 27.30, 34.35, 35.91, 38.94 (adamantane-C), 58.22 (CH2), 115.30, 124.46, 129.10, 142.75 (Ar—C), 168.20 (C = N), 176.77 (C = S). EI-MS, m/z (rel. int.): 377 (M+ + 2, 1), 359 (M+, 4), 236 (82), 176 (17), 142 (20), 140 (55), 135 (100), 113 (5), 111 (26).

Experimental details

The structure was refined as an inversion twin (BASF 0.43).

Discussion

The adamantyl group was identified as an essential pharmacophore in several bioactive drugs [1, 2]. Several adamantane derivatives are currently used as efficient therapies against influenza [3–5], herpes simplex [6] and HIV [7–9] viruses. In addition, numerous adamantane derivatives were reported to exhibit marked anticancer [10, 11], antibacterial [12–15] and antifungal [16] activities. In continuation to our ongoing interest in the chemical and biological properties of adamantane derivatives, we report herein the crystal structure of the title compound which displayed potent broad spectrum antibacterial activity [9]. The title compound is a functionalized 1,3,4-oxadiazole-2-thione derivative. The benzene ring makes a dihedral angle of 57.43(5)° with the 1,3,4-oxadiazole-2-thione. In the crystal, the N3—H3⋯S1 hydrogen-bonding interactions link the molecules into chains extending along the c direction. The distance of N and H3 is 2.57(4) Å and the angle is 171.0 (3)°.


Corresponding author: Hazem A. Ghabbour, Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud, University, Riyadh 11451, Saudi Arabia, e-mail: ; and Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt

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. We also acknowledge the financial support from Spanish Ministerio de Economía y Competitividad (MINECO-13-MAT2013–40950-R, FPI grant BES-2011–046948 to MSM-A).

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Received: 2015-11-26
Accepted: 2016-1-7
Published Online: 2016-1-29
Published in Print: 2016-3-1

©2016 Monirah A. Al-Alshaikh et al., published by De Gruyter.

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

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  46. Crystal structure of catena-poly[diaqua-μ2-4,4′-biphenyl-4,4′-diyldipyridine-κ2N:N′-bis(5-carboxy-2,6-dimethylpyridine-3-carboxylato-κO)nickel(II)] dihydrate, C40H40N4O12Ni
  47. Crystal structure of poly-[μ2-4,4′-bipyridine-κ2N:N′−μ3-thiophene-2,3-di-carboxylato-κ4O,O′, O′′:O′′′ -cadmium(II)]
  48. Crystal structure of hexaaquamanganese(II) bis(3-carboxythiophene-2-carboxylate) C12H18MnO14S2
  49. Crystal structure of 4-(3-(pyridin-3-yl)-1H-1,2,4-triazol-5-yl)benzoic acid, C14H10N4O2
  50. Crystal structure of (E)-2-(benzo[d]thiazol-2-yl)-3-(pyridin-3-yl)acrylonitrile)
  51. Crystal structure of catena-poly[2,2′-bipyridinyl-6,6′-dicarboxylato-κ4N,N′,O,O′)-(μ2-2,2′-bipyridinyl-6′-carboxyl-6-carboxylato-κ5N,N′,O,O′:O′′)samarium(III)] monohydrate, C24H13N4O8Sm · H2O
  52. Crystal structure of catena-poly[bis(μ2-4-(3-(pyridin-3-yl)-1H-1,2,4-triazol-5-yl)benzoato)-κ2N:O)copper(II)] dihydrate, C28H22N8O6Cu
  53. Crystal structure of catena-poly[tetraaqua-(μ2-4,4′-bipyridine-k2N:N′)-zinc(II)] fumarate tetrahydrate, C14H26N2O12Zn
  54. Crystal structure of triaqua-(1,10-phenanthroline)-(dihydrogen-3,3′,3′′-(2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tripropanoato) cobalt(II)dihydrogen-3,3′,3′′-(2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tripropanoate, C72H82Co2N16O42
  55. Crystal structure of poly[dibromido-(μ2–4,4′-bis-(pyrid-4-yl)biphenyl-κ2N:N′)lead(II)], C22H16N2PbBr2
  56. Crystal structure of catena-poly[diaqua-bis(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:N)-cobalt(II)]dihydrate, C26H24N2O12Co
  57. Crystal structure of 5-(4-pyridyl)pyrimidine–4,4′-bipyridine–1,3,5-benzenetriol–water (1:1:1:1), C25H23N5O4
  58. Crystal structure of 5-hydroxy-4-((4-hydroxyphenyl)imino)naphthalen-1(4H)-one monohydrate, C16H11NO3 · 0.5H2O
  59. Crystal structure of 2-amino-N-(4-methoxyphenyl)benzamide, C14H14N2O2
  60. Crystal structure of (2,5-dihydroxyphenyl)-(4-hydroxy-3,5-dimethoxyphenyl)methanone, C15H14O6
  61. Crystal structure of dichlorido[bis(2-hydroxyethyl)5′-([2,2′:6′,2′′-terpyridin]-4′-yl)-[1,1′:3′,1′′-terphenyl]-4,4′′-dicarboxylato]zinc(II), C39H31Cl2N3O6Zn
  62. Crystal structure of bis[4-(3-carboxy-6-fluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium] benzene-1,4-dicarboxylate (C20H18F2N3O3)2(C8H4O4), C48H40F4N6O10
  63. Crystal structure of (2,5-dihydroxyphenyl)-(4-methoxyphenyl)methanone, C14H12O4
  64. Crystal structure of photochromic 1-(2-methyl-5-phenyl-3-thienyl-2-[2-methyl-5-(4-ethoxylphenyl)-3-thienyl] 3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H22F6OS2
  65. Crystal structure of poly[diaquabis(μ2-biphenyl-2,4′-dicarboxylato-κ2O:O′)tris(μ2-1,1′-biphenyl-4,4′-diylbis(1H-imidazole)-κ2N:N′)dicobalt(II)] monohydrat, C82H64N12O11Co2
  66. Crystal structure of 2-amino-4-(3,4-difluorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H12N2O2F2
  67. Crystal structure of poly[(di-μ2-aqua-κ2O:O)bis(μ5-oxalato-1:2κ2O1; 1κ1O2; 3:4:5κ3O3; 3κ1O4)(μ4-oxalato-1:2κ2O1; 2:3κ2O2; 3:4κ2O3; 4:1κ2O4)dizinc(II)disodium(I)]
  68. Crystal structure of tetraethylammonium hexachloridotantalate(V), C8H20Cl6NTa
  69. Crystal structure of (E)-2,4-dibromo-6-(((2-nitrophenyl)imino)methyl)phenol, C13H8Br2N2O3
  70. The crystal structure of 6-chloro-2,4-diphenylquinoline
  71. Crystal structure of (E)-2-(((1,10-phenanthrolin-5-yl)imino)methyl)-5-methylphenol monohydrate, C20H15N3O·H2O
  72. Crystal structure of tris(3-(2-pyridyl)pyrazole)zinc(II)tetrachlorido zincate(II), C24H21Cl4N9Zn2
  73. Crystal structure of 4-chloro-N,N-diethyl-6-(piperidin-1-yl)-1,3,5-triazin-2-amine, C12H20ClN5
  74. The crystal structure of 4-allyl-5-benzyl-2,4-dihydro-3H-1,2,4-triazol-3-one, C12H13N3O
  75. Crystal structure of diethyl 2-(((2-(pyridin-3-ylthio)phenyl)amino)methylene)malonate, C19H20N2O4S
  76. Crystal structure of fac-tricarbonyl(2-(isopropylimino)methyl-5-methylphenolatido-κ2N,O)(pyridine-κN)rhenium(I), C19H19N2O4Re
  77. Crystal structure of 1,3,6,8-tetrakis(p-tolylthio)pyrene, C44H34S4
  78. Crystal structure of catena-poly-(diaqua-(μ2-1,2-bis(4-pyridyl)ethene-κ2N:N′)-(4-methylphthalato-κ2O,O′)-cobalt(II)trihydrate, C21H26CoN2O9
  79. Crystal structure of tetraethylammonium fac-tricarbonyl(hexafluoroacetylacetonato-κ2O,O′)-(nitrato-κO)rhenium(I), C16H21O8N2F6Re
  80. Crystal structure of 3-(thiophen-2-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carboxamide
  81. Crystal structure of bis(1-ethyl-3-methylimidazolium) tetrabromidocadmate(II), [C6H11N2]2[CdBr4]
  82. Crystal structure of N′-(adamantan-2-ylidene)-isonicotinohydrazide, C16H19N3O
  83. Crystal structure of trans-tetraaquabis(4-(pyridin-4-ylsulfonyl)pyridine-κN)cobalt(II) diperchlorate dihydrate, C20H28Cl2CoN4O18S2
  84. Crystal structure of (Z)-4-(furan-2-yl(p-tolylamino)methylene)-3-methyl-1-p-tolyl-1H-pyrazol-5(4H)-one, C23H21N3O2
  85. Crystal structure of 2-[(4-fluorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile, C16H16FN3OS
  86. Crystal structure of poly[octaaqua-tris(benzene-1,2,4,5-tetracarboxylato)tetralanthanum(III)] hexahydrate, C30H34La4O38
  87. Crystal structure of trans-tetraaqua-bis(4,4′-sulfonyldipyridine-κN)zinc(II) diperchlorate dihydrate, C20H28Cl2ZnN4O18S2
  88. Crystal structure of 4-nitro-thiophene-2-carboxylic acid, a structure with a Z′ = 4, C5H3NO4S
  89. Crystal structure of dirubidium trimercury(II) tetraselenide, Rb2Hg3Se4
  90. Crystal structure of 5-(adamantan-1-yl)-3-[(4-chloroanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, C19H22ClN3OS
  91. Crystal structure of hexaaquamagnesium(II) 5,5′-bitetrazole-1,1′-diolate, C2H12N8O8Mg
  92. The crystal structure of catena-poly[(μ2-1,1′-benzene-1,4-diylbis(1H-benzimidazole-κ2N:N′)silver(I)] nitrate, C20H14N5AgO3
  93. The crystal structure of 1-(2-(4-chlorophenoxy)-4-chlorophenyl)ethanone, C14H10Cl2O2
  94. The crystal structure of 3,5-dinitro-1,3,5-oxadiazinane, C3H6N4O5
  95. Crystal structure of methyl 5-methoxy 1H-indole-2-carboxylate, C11H11NO3
  96. Crystal structure of (Z)-1-(((3-acetyl-2-hydroxyphenyl)amino)methylene)naphthalen-2(1H)-one, C19H15NO3
  97. Crystal structure of (Z)-5-(4-chlorobenzylidene)-2-thioxothiazolidin-4-one —dimethylsulfoxide (1:1), C12H12ClNO2S3
  98. Crystal structure of 5,5′-((4-(trifluoromethyl)phenyl)methylene)bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione) – diethylamine – dichloromethane (1/1/1) C25H32Cl2F3N5O6
  99. Crystal structure of 2-(dimethylsulfanylidene)-N-(4-methoxyphenyl)-3-oxo-3-phenylpropanamide
  100. Crystal structure of (1,10-phenanthroline-κ2N,N′)bis(thiocyanato-κN)platinum(II), C14H8N4PtS2
  101. Crystal structure of di(μ2-chlorido)bis[2-(2-pyridyl)phenyl-κ2N,C1]dipalladium(II), C22H16Cl2N2Pd2
  102. Crystal structure of trans-dibromidodi(pyridine-κN)palladium(II), PdBr2(C5H5N)2
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