Home Crystal structure of (E)-N′-(4-methoxybenzylidene)-5-methyl-1-(4-tolyl)-1H-1,2,3-triazole-4-carbohydrazide, C19H19N5O2
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Crystal structure of (E)-N′-(4-methoxybenzylidene)-5-methyl-1-(4-tolyl)-1H-1,2,3-triazole-4-carbohydrazide, C19H19N5O2

  • Mohammad Hayal Alotaibi EMAIL logo
Published/Copyright: April 20, 2018

Abstract

C19H19N5O2, triclinic, P1̄ (no. 2), a = 6.6320(3) Å, b = 10.3272(5) Å, c = 13.0832(6) Å, α = 102.751(2)°, β = 96.130(2)°, γ = 103.079(2)°, V = 839.63(7) Å3, Z = 2, Rgt = 0.0553, wRref(F2) = 0.1521, T = 100(2) K.

CCDC no.: 1812851

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:

Data collection and handling.

Crystal:Colorless block
Size:0.45 × 0.31 × 0.18 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:25°, >99%
N(hkl)measured, N(hkl)unique, Rint:10420, 2930, 0.085
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2273
N(param)refined:242
Programs:Bruker programs [1], SHELX [2, 3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.6563(2)0.38424(16)0.31037(12)0.0265(4)
O2−0.1820(2)0.01614(16)0.67980(11)0.0216(4)
N10.7157(3)0.67425(18)0.12365(13)0.0167(4)
N20.5427(3)0.7158(2)0.15081(14)0.0236(5)
N30.4659(3)0.64357(19)0.21453(14)0.0220(5)
N40.3692(3)0.46333(19)0.34138(14)0.0200(4)
N50.3087(3)0.37662(18)0.40517(13)0.0195(4)
C10.8333(3)0.7349(2)0.05278(15)0.0169(5)
C21.0494(3)0.7823(2)0.07805(16)0.0191(5)
H2A1.12040.77610.14310.023*
C31.1613(3)0.8386(2)0.00830(17)0.0208(5)
H3A1.30970.87120.02620.025*
C41.0608(3)0.8486(2)−0.08818(16)0.0198(5)
C50.8428(4)0.8018(2)−0.11091(16)0.0215(5)
H5A0.77090.8094−0.17530.026*
C60.7285(3)0.7445(2)−0.04213(16)0.0205(5)
H6A0.58000.7120−0.05950.025*
C71.1835(4)0.9045(3)−0.16557(18)0.0282(6)
H7A1.29990.9829−0.12690.042*
H7B1.09160.9345−0.21420.042*
H7C1.23910.8328−0.20630.042*
C80.9204(4)0.5055(2)0.15524(18)0.0268(6)
H8A0.89270.42330.18270.040*
H8B1.05470.56810.19300.040*
H8C0.92640.47870.07920.040*
C90.7493(3)0.5756(2)0.17167(15)0.0168(5)
C100.5884(3)0.5571(2)0.22933(15)0.0166(5)
C110.5441(3)0.4606(2)0.29713(16)0.0190(5)
C120.1246(3)0.3688(2)0.42921(16)0.0207(5)
H12A0.03920.41990.40190.025*
C130.0448(3)0.2825(2)0.49789(16)0.0182(5)
C140.1714(3)0.2124(2)0.54576(16)0.0192(5)
H14A0.31350.22440.53550.023*
C150.0933(3)0.1277(2)0.60651(16)0.0199(5)
H15A0.18130.08150.63810.024*
C16−0.1153(3)0.1083(2)0.62275(15)0.0179(5)
C17−0.2414(3)0.1802(2)0.57919(16)0.0194(5)
H17A−0.38150.17110.59220.023*
C18−0.1604(3)0.2653(2)0.51645(16)0.0211(5)
H18A−0.24760.31280.48560.025*
C19−0.4003(3)−0.0186(2)0.68669(18)0.0248(5)
H19A−0.4329−0.09860.71640.037*
H19B−0.4832−0.04030.61560.037*
H19C−0.43450.05930.73280.037*
H1N40.287(4)0.517(3)0.324(2)0.041(8)*

Source of material

The title compound was synthesized during the reaction of 5-methyl-1-(4-tolyl)-1H-1,2,3-triazole-4-carbohydrazide and anisaldehyde in boiling anhydrous ethanol containing glacial acetic acid as a catalyst for 2 h. The solid obtained was crystallized using dimethylformamide (Mp 239–240 °C) [4].

Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Discussion

N′-Arylidene carbohydrazides are useful in terms of their biological activities [5, 6] . Also, 1,2,3-triazoles are biologically active compounds with many medicinal applications [7], [8], [9], [10], [11], [12].

The dihedral angles between central triazole ring (C9/C10/N1—N3) and tolyl ring (C1—C6) and phenyl ring (C13—C18) system are 48.71° and 18.04°, respectively. The packing structure shows at least two non-classical hydrogen bonds between C7—H7B⋯O2i and C12—H12A⋯O1ii with symmetry code: (i) x + 1, y + 1, z − 1; (ii) x − 1, y, z.

References

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Received: 2018-01-03
Accepted: 2018-04-04
Published Online: 2018-04-20
Published in Print: 2018-07-26

©2018 Mohammad Hayal Alotaibi, published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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  71. Crystal structure of 2-isopropyl-8-methyl-phenanthrene-3,4-dione, C18H16O2
  72. Crystal structure of 2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione, C19H22O2
  73. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-4-bromophenol, C14H13BrN2O
  74. Crystal structure of 1,1-di(4-cyanophenyl)-2,2-diphenylethene, C28H18N2
  75. Crystal structure of bis(hydroxylamido-κ2O,N)-oxido(1H-pyrazole-3-carboxylato-κ2O,N)vanadium(V), C4H7N4O5V
  76. The crystal structure of In1.2B3O5.6(OH)1.4
  77. The crystal structure of chlorido(2-(1H-pyrazol-3-yl)phenolato-κ2N,O)(2-(1H-pyrazol-3-yl)phenol-κN)copper(II), C18H15ClCuN4O2
  78. Crystal structure of 1-heptylpyridazin-1-ium iodide, C11H19N2I
  79. The crystal structure of N-butylpyridinium bis(μ2-dichlorido)-tetrachloridodicopper(II), C18H28N2Cu2Cl6
  80. Crystal structure of 6-hydroxy-5-((2-hydroxy-6-oxocyclohex-1-en-1-yl)(4-methoxyphenyl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, C20H22N2O6
  81. Crystal structure of bis(acetonitrile)-diaqua-dichloridoiron(II), C4H10Cl2N2O2Fe
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