Home Crystal structure of 3-(4-hydroxy-3-methoxyphenyl)-N-phenylpropanamide, C16H17NO3
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Crystal structure of 3-(4-hydroxy-3-methoxyphenyl)-N-phenylpropanamide, C16H17NO3

  • Inese Mierina , Emilis Gudelis , Dmitrijs Stepanovs EMAIL logo , Mara Jure EMAIL logo , Anatoly Mishnev , Maria Kolympadi and Dean Marković
Published/Copyright: March 17, 2016

Abstract

C16H17NO3, orthorhombic, P212121 (no. 19), a = 7.9882 (2) Å, b = 11.4053 (3) Å, c = 16.2381 (5) Å, V = 1479.42 (7) Å3, Z = 4, Rgt(F) = 0.0480, wRref(F2) = 0.0991, T = 173 K.

CCDC no.:: 1428589

The crystal structure is shown in the figure (upper part). The hydrogen bonded connection of adjacent molecules is shown in the lower part of 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:Colorless, plate, size 0.09×0.24×0.28 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.84 cm−1
Diffractometer, scan mode:Nonius Kappa CCD, φ and ω scan
2θmax:54.98°
N(hkl)measured, N(hkl)unique:3394, 3394
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2516
N(param)refined:190
Programs:SIR2011 [16], WinGX [17], Nonius data collection and reduction software [18], SHELX [19]
Table 2:

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

AtomSitexyzUiso
H(3)4a0.306(4)−0.172(2)0.873(2)0.061(8)
H(1)4a0.383(3)0.425(2)0.560(2)0.041(7)
H(2A)4a0.44910.20420.55670.038
H(2B)4a0.29620.14250.51490.038
H(3A)4a0.25700.30180.64750.041
H(3B)4a0.11240.22620.60940.041
H(5)4a0.05170.04180.67540.038
H(6)4a0.1150−0.10130.77260.036
H(9)4a0.50420.18510.70850.030
H(10A)4a0.76450.12560.74720.064
H(10B)4a0.83540.10640.83620.064
H(10C)4a0.69050.19670.82140.064
H(12)4a0.14960.49380.39310.043
H(13)4a0.15560.67060.32390.051
H(14)4a0.34180.81500.36030.057
H(15)4a0.53150.78110.46570.059
H(16)4a0.53590.60110.53230.046
Table 3:

Fractional atomic coordinate and displacement parameters (Å2).

AtomSitexyzU11U22U33U12U13U23
O(1)4a0.2809(2)0.2988(1)0.40942(8)0.0417(9)0.0282(7)0.0199(7)−0.0032(6)−0.0044(6)−0.0007(5)
O(2)4a0.6158(2)0.0323(1)0.81828(8)0.0290(7)0.0354(7)0.0292(7)−0.0038(7)−0.0069(6)0.0073(6)
O(3)4a0.3950(2)−0.1221(1)0.85765(9)0.0400(9)0.0292(7)0.0338(8)−0.0033(7)−0.0066(7)0.0114(7)
N(1)4a0.3473(3)0.4219(1)0.5129(1)0.056(1)0.0267(9)0.0226(9)−0.0064(8)−0.0131(9)0.0006(7)
C(1)4a0.3165(3)0.3147(2)0.4827(1)0.030(1)0.026(1)0.026(1)−0.0009(9)−0.0018(9)0.0004(8)
C(2)4a0.3319(3)0.2137(2)0.5425(1)0.041(1)0.027(1)0.027(1)−0.000(1)−0.005(1)0.0016(8)
C(3)4a0.2309(3)0.2269(2)0.6223(1)0.030(1)0.038(1)0.034(1)0.002(1)−0.0039(9)0.0115(9)
C(4)4a0.2687(3)0.1295(2)0.6829(1)0.030(1)0.030(1)0.023(1)0.0035(9)0.0019(9)0.0020(8)
C(5)4a0.1551(3)0.0429(2)0.7017(1)0.029(1)0.038(1)0.028(1)−0.001(1)−0.0054(9)0.0039(9)
C(6)4a0.1933(3)−0.0437(2)0.7600(1)0.032(1)0.027(1)0.030(1)−0.0046(9)0.0005(9)0.0020(9)
C(7)4a0.3469(3)−0.0433(2)0.7986(1)0.035(1)0.0218(9)0.0211(9)0.003(1)−0.0014(8)0.0022(8)
C(8)4a0.4654(2)0.0423(2)0.7779(1)0.027(1)0.026(1)0.0200(9)−0.0004(9)−0.0022(8)−0.0016(8)
C(9)4a0.4257(2)0.1277(2)0.7214(1)0.029(1)0.0247(9)0.022(1)−0.0009(9)0.0032(8)0.0017(8)
C(10)4a0.7364(3)0.1227(2)0.8047(1)0.033(1)0.051(1)0.042(1)−0.010(1)−0.009(1)0.009(1)
C(11)4a0.3436(3)0.5294(2)0.4688(1)0.042(1)0.025(1)0.023(1)−0.003(1)0.0003(9)0.0010(8)
C(12)4a0.2282(3)0.5506(2)0.4071(1)0.044(1)0.028(1)0.034(1)−0.002(1)−0.006(1)−0.0009(9)
C(13)4a0.2310(3)0.6572(2)0.3665(1)0.054(2)0.034(1)0.040(1)0.005(1)−0.011(1)0.0070(9)
C(14)4a0.3425(4)0.7434(2)0.3877(1)0.065(2)0.031(1)0.046(1)−0.004(1)−0.001(1)0.012(1)
C(15)4a0.4562(4)0.7228(2)0.4505(1)0.068(2)0.036(1)0.043(1)−0.019(1)−0.002(1)0.004(1)
C(16)4a0.4583(3)0.6154(2)0.4908(1)0.051(1)0.037(1)0.029(1)−0.010(1)−0.006(1)0.002(1)

Source of material

3-(4-Hydroxy-3-methoxyphenyl)-N-phenylpropanamide was obtained by a method which is similar to a known procedure [1]: 3-(4-hydroxy-3-methoxyphenyl)-N-phenylprop-2(E)-enamide (50 mg, 0.2 mmol) and hydrazine hydrate (0.1 mL, 2 mmol) were refluxed in ethanol (2 mL) for 16 h. When the reaction was completed the mixture was poured into ice and acidified with concentrated hydrochloric acid. The water solution was extracted with ethyl acetate (4 × 6 mL); the organic layers were combined, dried over MgSO4 and evaporated. The title compound was obtained as colorless crystals (21 mg, 39%) with a melting temperature of 402 K (129 °C). The compound is known and its spectral data correspond to those reported in literature [2]. Single crystals were obtained by slow evaporation from ethyl acetate.

Experimental details

Hydrogen atoms at the amino and hydroxy group were located in a difference Fourier map and freely refined. The C-bound hydrogen atoms were positioned geometrically with C—H distances ranging from 0.93 to 0.97 Å and refined as riding on their parent atoms with Uiso(H) = 1.5Ueq(C) for methyl groups and Uiso(H) = 1.2Ueq(C) for other H atoms.

Discussion

3-Aryl-N-arylpropanamides rise interest both due to synthetic applications and wide range of biological activity (e. g., they act as antitubercular [3] and antibiotic [4] agents, as well as HCA2 receptor agonists [5]). These compounds serve as starting materials for synthesis of 3-arylpropanols [6], 1,3-diarylpropan-1-ones [7], quinolines [8], β-l lactams [9], 4-aryl-2-quinolinones [10] and 1-indanones [11], as well as ligands in iridium complexes [12]. Despite the wide application of these compounds only few structures have been analyzed by X-ray diffraction method: the closest examples include 1,3-di-(3-phenylpropanoylamino)benzene [13], N-ethyl-3-phenyl-N-[2-[(3-phenyl-5-isoxazolyl)methylamino] phenyl]propanamide [14] and 3-aryl-N-phenylpropanamides containing nitrogen heterocycle in para-position of dihydrocinnamoyl moiety [15]. However this is the first example, of a crystal structure of dihydroferulic acid anilide. The title compound is achiral, but it crystallizes in chiral space group (P21 21 21). Secondary amino group participates in bifurcated hydrogen bond, where acceptors are oxygen atoms of hydroxy and methoxy groups (N—H⋯O type, dD⋯A = 2.984(3) and 3.031(2) Å, respectively). Meanwhile the hydroxy group is the donor of O—H⋯O type hydrogen bond ( dD⋯A = 2.597(2) Å), where acceptor is oxygen atom of carbonyl group. By means of these hydrogen bonds the three-dimensional molecular networks are formed (lower part of the figure showing one molecule with two adjacent ones). The 4-hydroxy-3-methoxyphenyl fragment is almost planar.


Corresponding authors: Dmitrijs Stepanovs, Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, LV 1006, Latvia; and Faculty of Materials Science and Applied Chemistry, Riga Technical University, P.Valdena 3/7, Riga, LV 1048, Latvia, e-mail: ; and Mara Jure, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P.Valdena 3/7, Riga, LV 1048, Latvia, e-mail:

Acknowledgements:

Authors thank master student Agnese Stikute (Riga Technical University) for the synthesis of starting compound ferulanilide. E.G. acknowledges ERASMUS+ mobility grant for the opportunity of traineeship at RTU.

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Received: 2015-10-9
Accepted: 2016-2-12
Published Online: 2016-3-17
Published in Print: 2016-6-1

©2016 Inese Mierina et al., published by De Gruyter.

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

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  54. Crystal structure of N,N-diethyl-2-(2-(6-(4-methoxybenzyl)-7-oxo-7H-thiazolo[3,3-b][1,2,4]triazin-3-yl)phenoxy)acetamide, C25H26N4O4S
  55. Crystal structure of tetraqua((E)-4,4′-(diazene-1,2-diyl)bis(5-oxo-4,5-dihydro-1,2,4-triazol-1-ide)-κ2N:O)barium(II), C4H10N8O6Ba
  56. Crystal structure of 2-amino-4-(3-phenoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C22H18N2O3
  57. Crystal structure of diethylammonium 5-((4-fluorophenyl)(6-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate, C23H30FN5O6
  58. Crystal structure of 2-amino-4-(3,5-difluoro-phenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H12F2N2O2
  59. Crystal structure of tris(N-nitroso-N-oxyanilino-κ2O, O′) oxidoniobium(V), C18H15N6O7Nb
  60. Crystal structure of 1-(5-benzoyl-4-methyl-2-(phenylamino)thiophen-3-yl)ethan-1-one, a structure with Z′ = 6, C20H17NO2S
  61. Crystal structure of diethyl-3-methyl-4-phenylthieno[2,3-b]thiophene-2,5-dicarboxylate, C19H18O4S2
  62. Crystal structure of 3,5-dicarboxybenzoate — benzene-1,3,5-tricarboxylic acid (1/1), C24H22N2O12
  63. The crystal structure of 2-chloro-1,3-bis(2,4,6-trimethylphenyl)-4,4-dimethyl-1,3,2λ3,4-diazaphosphasiletidine
  64. Crystal structure of hexaquamanganese(II) bis(hexaborato-κ3O,O′,O′′)manganese(II) dihydrate, B12H28Mn2O34
  65. Crystal structure of 1-propyl-3-methylimidazolium pentaborate, [C7H13N2][B5O6(OH)4]
  66. Crystal structure of 13-(4-fluorophenyl)-11,13-dihydro-1H-benzo[h]indazolo[6,7-b] [1, 6]naphthyridin-12(6H)-one — dimethylformamide — water (1/2/1), C29H31FN6O4
  67. Crystal structure of 1-(2-chlorophenyl)-2-(2-nitrophenyl)ethan-1-ol, C14H12ClNO3
  68. Crystal structure of (Z)-2-((2-bromo-1-phenylvinyl)oxy)benzonitrile, C15H10BrNO
  69. Crystal structure of tetrachlorido(1E,1′E)-N,N′-((1,4-phenylenebis(propane-2,2-diyl))bis(4,1-phenylene))bis(1-(pyridin-2-yl-κN)methanimine-κN)dizinc(II), C36H34N4Zn2Cl4
  70. Crystal structure of 2,6-bis(3-methylpyridinyl)hexahydro-4,8-ethenopyrrolo-[3,4-f]isoindole-1,3,5,7(2H,6H)-tetrone, C24H20N4O4
  71. Crystal structure of trans-bis(2-methylmaleato-κ2O,O′) bis(piperazinium-κN) cobalt(II) trihydrate, C18H36CoN4O11
  72. Crystal structure of (E)-4-chloro-N′-(4-(diethylamino)benzylidene)benzohydrazide, C18H20ClN3O
  73. Crystal structure of 3,6-di(1H-imidazol-1-yl)-9H-carbazole, C18H13N5
  74. Crystal structure of 4-(4-pyridinyl)-1-naphthoic acid, C16H11NO2
  75. Crystal structure of 1,1′-diformyl-4,4′-(6H,12H-5,11-methano-dibenzo[b,f][11,5]diazocine-2,8-diyl)dibenzene, C29H22N2O2
  76. Crystal structure of N′-(adamantan-2-ylidene)pyridine-3-carbohydrazide, C16H19N3O
  77. Crystal structure of 1,1′-(butane-1,4-diyl)bis(5-methyl-1H-pyrazole-3-carbaldehyde), C14H18N4O2
  78. Crystal structure of methyl 8-hydroxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-decahydrocyclohepta[e]indene-3a(1H)-carboxylate, C21H34O3
  79. Crystal structure of 6-oxo-4-propyl-2-(propylthio)-1,6-dihydropyrimidine-5-carbonitrile, C11H15N3OS
  80. Crystal structure of poly[diacetato(μ2-1,4-bis(1H-imidazol-1-yl)benzene-κ2N:N′)nickel(II)], C26H22N8NiO4
  81. Crystal structure of bis(2,4-dibromo-6-{(E)[(4-fluorobenzyl)imino]methyl}phenolato-κ2N,O) copper(II), C28H18Br4F2N2O2Cu
  82. Crystal structure of 1-(adamantan-1-yl)-3-phenylthiourea, C17H22N2S
  83. Crystal structure of 3-(6-(5-amino-1-phenyl-1H-pyrazol-3-yl)pyridin-2-yl)-1-phenyl-1H-pyrazol-5-amine – dioxan (2/1), C25H23N7O
  84. Crystal structure of 5-ethyl-6-[(3-methylphenyl)sulfanyl]pyrimidine-2,4(1H,3H)-dione, C13H14N2O2S
  85. Crystal structure of (((1E,1′E)-(cyclohexane-1,2-diylbis(azanylylidene-κ2N,N′))bis(methanylylidene))bis(2,1-phenylene))bis((2,6-diisopropylphenyl)amide-κ2N′′,N′′′)manganese(II), C44H54N4Mn
  86. Crystal structure of prop-2-en-1-yl 2-oxo-2H-1-benzopyran-3-carboxylate, C13H10O4
  87. Crystal structure of bis(μ2-2-((3-methylphenyl)imino)methylphenolato-κ2N,O:O)hexacarbonyldimanganese(I), C34H24Mn2N2O8
  88. Crystal structure of (Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxybut-2-en-1-one C9H12N2O2
  89. Crystal structure of 2,2′-[pentane-1,5-diylbis(oxy)]dibenzaldehyde, C19H20O4
  90. Crystal structure of 2-phenyl-5,6,7,8-tetrahydro-4H-benzo[4,5]thieno[2,3-d][1,3]oxazin-4-one, C16H13NO2S
  91. Crystal structure of (E)-1-(2-chlorophenyl)-N-(4-chlorophenyl)methanimine, C13H9Cl2N
  92. Crystal structure of ethyl 2-amino-5-bromothiazole-4-carboxylate, C6H7BrN2O2S
  93. Crystal structure of 2-benzylisothiouronium tetraphenylborate, C32H31BN2S
  94. Crystal structure of poly[(μ2-biphenyl-2,2′-dicarboxylato-κ4O,O′:O′′,O′′′)(μ2-4,4′-bipyridine-κ2N:N′)copper(II)], C24H16CuN2O4
  95. Crystal structure of (η5-pentamethylcyclopentadienyl)titanium(III)dichloride (THF), C14H23Cl2OTi
  96. Crystal structure of 3-ferrocenylsulfonyl-2-(4-methoxyphenyl)-3H-imidazo[4,5-b]pyridine, C23H19FeN3O3S
  97. Crystal structure of 2-benzoyl-3-(4-fluorophenyl)cyclopropane-1,1-dicarbonitrile, C18H11FN2O
  98. Crystal structure of 1,6-ditosyl-1,6-diazecane, C22H30N2O4S2
  99. Crystal structure of N-phenyl-2-(pyridin-4-ylcarbonyl)hydrazinecarboxamide with Z′ = 4, C13H12N4O2
  100. Crystal structure of N,N-bis(diphenylphosphanyl)cyclohexylamine, C30H31NP2
  101. Crystal structure of 3-(4-hydroxy-3-methoxyphenyl)-N-phenylpropanamide, C16H17NO3
  102. Crystal structure of 6-(2-fluorophenyl)-3-phenyl-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazole, C15H9FN4S
  103. Crystal structure of catena-poly[aqua(dicyanoazanido-2κN-μ2-dicyanoazanido-1κN:2κN′)(μ2-2-methoxy-6-(((2-((3-methoxy-2-oxidobenzylidene)amino)ethyl)imino)methyl)phenolato-1κ2N,N′,2κ2O,O′,1κ2O′′,O′′′:2κ2O′′,O′′′)cadmium(II)copper(II)], C22H20CdCuN8O5
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