Home Crystal structure of 4,5-diphenylthiazol-2-amine, C15H12N2S
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Crystal structure of 4,5-diphenylthiazol-2-amine, C15H12N2S

  • Hazem A. Ghabbour EMAIL logo , Hatem A. Abdel-Aziz , Haitham AlRabiah and Obaid S. Alruqi
Published/Copyright: April 18, 2016

Abstract

C15H12N2S, monoclinic, P21/c (no. 14), a = 6.8853(3) Å, b = 23.8495(10) Å, c = 7.5689(3) Å, β = 96.585(2)°, V = 1234.70(9) Å3, Z = 4, Rgt(F) = 0.0506, wRref(F2) = 0.1243, T = 100 K.

CCDC no.:: 1429948

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:Yellow, plate, size 0.084×0.354×0.478 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:2.43 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω scans
2θmax:61.04°
N(hkl)measured, N(hkl)unique:17571, 3729
N(param)refined:171
Programs:Bruker programs [7], SHELX [8]
Table 2:

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

AtomSitexyzUiso
H(5A)4e0.55320.65030.92590.022
H(6A)4e0.82270.69371.08480.028
H(7A)4e1.13230.65261.10170.026
H(8A)4e1.17160.56760.95660.024
H(9A)4e0.90400.52390.79520.020
H(11A)4e0.06020.63890.57690.021
H(12A)4e0.01970.72750.44790.028
H(13A)4e0.28380.77420.34810.029
H(14A)4e0.59240.73230.38070.030
H(15A)4e0.63700.64370.51170.024
H(2N2)4e0.024(4)0.448(1)0.575(3)0.035(6)
H(1N2)4e0.162(4)0.415(1)0.699(3)0.033(6)
Table 3:

Fractional coordinates and atomic displacement parameters (Å2).

AtomSitexyzU11U22U33U12U13U23
S(1)4e0.49472(6)0.48334(2)0.78053(5)0.0164(2)0.0119(2)0.0130(2)−0.0007(2)−0.0027(1)0.0009(1)
N(1)4e0.2283(2)0.53650(6)0.5803(2)0.0139(7)0.0126(6)0.0129(6)−0.0003(5)0.0004(5)−0.0006(5)
N(2)4e0.1539(2)0.44137(6)0.6232(2)0.0172(8)0.0129(7)0.0174(7)−0.0021(6)−0.0030(6)0.0018(5)
C(1)4e0.2702(3)0.48713(7)0.6509(2)0.0154(8)0.0145(7)0.0106(7)−0.0005(6)0.0016(6)−0.0009(6)
C(2)4e0.3769(2)0.57475(7)0.6319(2)0.0145(8)0.0127(7)0.0112(7)0.0004(6)0.0013(6)−0.0008(5)
C(3)4e0.5306(2)0.55469(7)0.7438(2)0.0141(8)0.0110(7)0.0135(8)0.0001(6)0.0016(6)0.0005(5)
C(4)4e0.7017(2)0.58295(7)0.8408(2)0.0164(9)0.0126(7)0.0125(7)−0.0023(6)−0.0003(6)0.0014(5)
C(5)4e0.6788(3)0.63348(7)0.9304(2)0.0204(9)0.0147(7)0.0194(8)0.0010(7)−0.0015(7)−0.0002(6)
C(6)4e0.8393(3)0.65912(7)1.0259(2)0.032(1)0.0149(8)0.0213(9)−0.0052(7)−0.0019(8)−0.0027(6)
C(7)4e1.0233(3)0.63489(8)1.0362(2)0.023(1)0.0246(9)0.0164(8)−0.0111(8)−0.0020(7)0.0010(7)
C(8)4e1.0461(3)0.58455(8)0.9499(2)0.0151(9)0.0281(9)0.0152(8)−0.0019(7)0.0001(6)0.0023(7)
C(9)4e0.8865(3)0.55860(7)0.8532(2)0.0180(9)0.0182(8)0.0133(8)−0.0016(7)0.0017(6)−0.0001(6)
C(10)4e0.3535(3)0.63210(7)0.5579(2)0.0177(9)0.0126(7)0.0111(7)0.0002(6)−0.0021(6)−0.0012(6)
C(11)4e0.1692(3)0.65766(7)0.5377(2)0.0202(9)0.0143(8)0.0166(8)−0.0003(6)−0.0028(7)−0.0035(6)
C(12)4e0.1451(3)0.71033(7)0.4604(2)0.028(1)0.0163(8)0.0218(9)0.0056(7)−0.0097(8)−0.0032(6)
C(13)4e0.3016(3)0.73819(7)0.4015(2)0.041(1)0.0131(8)0.0176(9)0.0006(8)−0.0058(8)0.0018(6)
C(14)4e0.4844(3)0.71327(8)0.4208(2)0.035(1)0.0173(8)0.0220(9)−0.0046(8)0.0032(8)0.0040(7)
C(15)4e0.5110(3)0.66045(7)0.4988(2)0.0210(9)0.0163(8)0.0212(9)−0.0006(7)0.0014(7)0.0027(6)

Source of material

2-Hydroxy-1,2-diphenylethanone (1 equiv) was dissolved in CH2Cl2 (70 mL), SOCl2 (4 equiv), and 3 or 4 drops of DMF were added at 0°C, and the reaction was stirred for 1 h at 0°C. After completion of reaction, CH2Cl2 and SOCl2 were removed in vacuum. Water (80 mL) and EtOAc (150 mL) were added to the residue, and the EtOAc layer was separated, dried with Na2SO4, filtered, and concentrated. The product (1 equiv) and thiourea (1.2 equiv) were vigorously stirred in EtOH (10 mL) at 80°C for 15 h. The progress of the reaction was monitored by TLC. After completion of the reaction, EtOH was evaporated, the precipitated crude product was filtered, dried and crystallized from ethanol to yield (70%) of the title compound (C15H12N2S) as yellow plate crystals; mp: 214–217°C [1].

Experimental details

The hydrogen atoms were placed on calculated positions using a riding model (AFIX 43 option of the SHELX program [8]).

Discussion

2-Aminothiazole derivatives are greatly used as structural motifs in pharmaceutical chemistry because of their wide range of applications in drug development. Several reports on the application of 2-aminothiazoles in the treatment of a diverse range of different diseases like Alzheimer's disease [2], chronic pain [3], cancer [4] , Huntington's disease [5] and anticonvulsant [6] appeared in the scientific literature over the last few years.

In the title compound, C15H12N2S, the asymmetric unit contains one crystallographic independent molecule. The thiazol ring (N1/S1/C1—C3) makes the dihedral angles 49.39(2)° and 39.91 (3)° with phenyl ring (C4—C9) and phenyl ring (C10—C15), respectively (figure). The structure shows one classical hydrogen bond crystallographic independent between N2—H2N2⋯N1 with the symmetry code: −x, −y+1, −z+1. The title molecules are pairwise connected by two symmetry related hydrogen bond.

Funding source: King Saud University

Award Identifier / Grant number: RGP-1436–038

Funding statement: The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for its funding of this research through the Research Group Project NO (RGP-1436–038).

Acknowledgements:

The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for its funding of this research through the Research Group Project NO (RGP-1436–038).

References

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Received: 2015-12-20
Accepted: 2016-3-23
Published Online: 2016-4-18
Published in Print: 2016-9-1

©2016 Hazem A. Ghabbour et al., published by De Gruyter.

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

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  73. Crystal structure of poly-[tetraaquabis(μ8-benzene-1,2,4,5-tetracarboxylato-1κ3O4:O6:O8:2κ4O2:O2:O5:O5:3κ4O1:O3:O5:O7)(di-μ3-hydroxido)-pentazinc(II)] decahydrate, C20H34O32Zn5
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  75. Crystal structure of 2-((dimethylamino)methylene)-5,5-Dimethylcyclohexane-1,3-dione, C11H17NO2
  76. Crystal structure of poly[1,4-bis(2-methylbenzimidazol)butane-κ2N:N′)bis(4,4′-oxybis(benzoato-κ4O,O′:O′′,O′′′)dicadmium] monohydrate, C48H38Cd2N4O10
  77. Crystal structure of 2-(3-(benzofuran-2-yl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-chlorophenyl)thiazole, C26H17ClFN3OS
  78. Crystal structure of bis(μ3-isophthalato-κ3O:O′:O′′)(μ2-1,4-\ bis((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)benzene-κ2N:N′)dizinc(II), C22H19N2O4Zn
  79. Crystal structure of poly[bis(adipate-κ4O,O′:O′′, O′′′)(1,4-bis(2-methyl-1H-benzo[d]imidazol-1-yl)benzene-κ2N:N′)dizinc(II), C36H38N4O8Zn2
  80. Crystal structure of N-(2-(2-oxoindolin-4-yl)ethyl)-N-propylpropan-1-aminium tetraphenylborate, C40H45BN2O
  81. Crystal structure of 1-(2,3-dihydro-4-methyl-3-phenyl-2-thioxothiazol-5-yl)-1-ethanone, C12H11NOS2
  82. Crystal structure of 3-(adamantan-1-yl)-1-[(4-benzylpiperazin-1-yl)methyl]-4-[(E)-(2,6-difluorobenzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione, C31H36F2N6S
  83. Crystal structure of 6-(4-chlorophenyl)-3-(thiophen-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]-thiadiazole, C13H7ClN4S2
  84. Crystal structure of bis(ethanaminium) poly[bis(hexaselenido-κ2Se1,Se6)palladate(II)], C4H16N2PdSe12
  85. Crystal structure of 2-(3-(benzofuran-2-yl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-4-phenylthiazole, C26H19N3OS
  86. Crystal structure of poly-[bis(μ3-5-hydroxyisophtalato-κ3O:O′:O′′)(μ2-1,4-bis(2-ethylbenzimidazol-1-ylmethyl)benzene-κ2N:N′)dizinc(II)], C40H30N4O5Zn2
  87. Crystal structure of poly-[(μ-1,4-bis(2-ethylbenzimidazol-1-ylmethyl)benzene-κ2N:N′)-bis(μ4-2,2′-(1,3-phenylene)diacetate-κ4O:O′:O′′:O′′′)dizinc(II)], C44H38N4O8Zn2
  88. Crystal structure of 5,17-bis-cyano-25,26,27,28-tetrapropyloxy-calix[4]arene, C42H46N2O4
  89. Crystal structure of poly-[μ-1,4-bis(2-ethylbenzimidazol-1-ylmethyl)benzene-κ2N:N′)-bis(μ3-5-hydroxyisophthalate(2–)-κ3O,O′:O′′)dicadmium(II)] monohydrate, C64H54N8O11Cd2
  90. Crystal structure of poly-[μ-1,4-bis(2-ethylbenzimidazol-1-ylmethyl)benzene-κ2N:N′)-bis(μ4-4,4′-sulfonyldibenzoato-κ4O:O′:O′′:O′′′)dicadmium(II)] monohydrate, C52H42N4O14Cd2
  91. Crystal structure of poly-[bis(μ4-adipato-κ4O:O′:O′′:O′′′)(μ2-1,4-bis((2-ethyl-1H-benzo[d]imidazol-1-yl)methyl)benzene-κ2N:N′)dizinc(II)], C38H42N4O8Zn2
  92. Crystal structure of (2-(2-chlorophenyl)-5-methyl-1,3-dioxan-5-yl)methanol, C12H15ClO3
  93. Crystal structure of 2-(4-Bromophenyl)-5-ethyl-1,3-dioxane-5-carboxylic acid, C13H15BrO4
  94. Crystal structure of (2-(4-bromophenyl)-5-ethyl-1,3-dioxan-5-yl)methanol, C13H17BrO3
  95. Crystal structure of 3-((1,3,5,7-tetraoxo-6-(pyridin-3-ylmethyl)-3,3a,4,4a,5,6,7,7a,8,8a-decahydro-4,8-ethenopyrrolo[3,4-f]isoindol-2(1H)-yl)methyl)pyridin-1-ium-κN-trichloridocobalt(II) hemihydrate, C24H22Cl3CoN4O4.5
  96. Crystal structure of 4-chloro-4′,6′-dichloro-2,2′-[propane-1,3-diyldioxybis(nitrilomethylidyne)]-diphenol, C17H14Cl3N2O4
  97. Crystal structure of 2-amino-4-(3-trifluoromethylphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C17H13F3N2O2
  98. Crystal structure of bis(benzoato-κO)bis(4,4′-((1H-1,2,4-triazol-1-yl)methylene)dibenzonitrile-κN)zinc(II), C48H32N10O4Zn
  99. Crystal structure of 3-methyl-2H-chromen-2-one, C10H8O2
  100. Crystal structure of catena-poly-[aqua-(2-carboxy-5-(3-carboxy-5-carboxylatophenoxy)benzoato-κO)(μ2-4,4′-di(1H-imidazol-1-yl)-1,1′-biphenyl-κ2N:N′)cobalt(II)], C34H24N4O10Co
  101. Crystal structure of 4,4′-di(1H-imidazol-1-yl)-1,1′-biphenyl, C36H28N8
  102. Crystal structure of 1-(3-chloropropyl)piperidin-1-ium tetraphenylborate, C32H37BClN
  103. Crystal structure of dimethyl 5-(benzylamino)isophthalate, C17H17NO4
  104. Crystal structure of dimethyl 5-(dibenzylamino)isophthalate, C24H23NO4
  105. Crystal structure of N-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioamide, C21H29N3S
  106. Crystal structure of (2,2′(cyclohexane-1,2-diylbis(nitrilo(E)methylylidene))diphenolato-κ4O,O′,N,N′)dimethanolmanganese(III) bromide, C22H28BrMnN2O4
  107. Crystal structure of 3,5,7-tris(morpholinomethyl)tropolone·0.67 hydrate, C22H33N3O5·0.67H2O
  108. Crystal structure of biphenyl-2,3′,5,5′-tetracarboxylic acid – 4,4′-biphenyl-4,4′-diyldipyridine (3/2), C49H34N3O8
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