Startseite Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
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Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O

  • Jie Liu ORCID logo , Qirui Liang , Jie Li und Lufei Xiao ORCID logo EMAIL logo
Veröffentlicht/Copyright: 31. Januar 2022

Abstract

C16H14N4O, triclinic, P 1 (no. 2), a = 8.721(5) Å, b = 12.116(5) Å, c = 13.413(5) Å, α = 88.870(5)°, β = 86.304(5)°, γ = 80.568(5)°, V = 1395.1(11) Å3, Z = 4, R gt (F) = 0.0543, wR ref (F2) = 0.1645, T = 298(2) K.

CCDC no.: 1889661

The asymmetric unit of the title crystal structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Yellow block
Size: 0.30 × 0.20 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Bruker Smart Apex, ω
θmax, completeness: 27.2°, 99%
N(hkl)measured, N(hkl)unique, Rint: 10,575, 5516, 0.049
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 4614
N(param)refined: 382
Programs: Bruker [1], Olex2 [2], SHELX [3]
Table 2:

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

Atom x y z Uiso*/Ueq
O1 0.27522 (14) −0.00568 (10) 0.97368 (9) 0.0592 (3)
N1 −0.19096 (13) 0.40970 (10) 0.52191 (8) 0.0399 (3)
N2 −0.10429 (16) 0.36964 (12) 0.43806 (9) 0.0561 (4)
N3 −0.30142 (17) 0.50571 (12) 0.39791 (10) 0.0542 (4)
N4 −0.05979 (15) 0.25301 (10) 0.91010 (9) 0.0459 (3)
C1 −0.1766 (2) 0.43079 (14) 0.36728 (12) 0.0554 (4)
H1 −0.143144 0.422569 0.300191 0.067*
C2 −0.30579 (18) 0.49041 (13) 0.49518 (11) 0.0486 (4)
H2 −0.379200 0.530468 0.539878 0.058*
C3 −0.15533 (16) 0.36630 (11) 0.61903 (10) 0.0374 (3)
C4 −0.00442 (17) 0.31836 (13) 0.63746 (11) 0.0467 (4)
H4 0.073667 0.313135 0.586365 0.056*
C5 0.03009 (17) 0.27809 (13) 0.73247 (11) 0.0474 (4)
H5 0.131223 0.245085 0.744640 0.057*
C6 −0.08605 (16) 0.28688 (11) 0.80966 (10) 0.0403 (3)
C7 −0.23677 (17) 0.33689 (12) 0.78968 (11) 0.0443 (3)
H7 −0.314487 0.344625 0.841076 0.053*
C8 −0.27283 (16) 0.37520 (12) 0.69484 (10) 0.0429 (3)
H8 −0.374386 0.406509 0.682006 0.052*
C9 0.04335 (17) 0.16986 (12) 0.92953 (11) 0.0434 (3)
H9 0.103346 0.131608 0.877325 0.052*
C10 0.06955 (17) 0.13305 (12) 1.03295 (10) 0.0423 (3)
C11 0.18528 (17) 0.04162 (12) 1.05393 (11) 0.0455 (3)
C12 0.2038 (2) 0.00462 (14) 1.15214 (12) 0.0572 (4)
H12 0.279977 −0.055990 1.165876 0.069*
C13 0.1090 (2) 0.05807 (15) 1.22906 (12) 0.0626 (5)
H13 0.121980 0.033074 1.294452 0.075*
C14 −0.0051 (2) 0.14824 (15) 1.21012 (12) 0.0598 (4)
H14 −0.068159 0.183912 1.262373 0.072*
C15 −0.0244 (2) 0.18481 (13) 1.11280 (12) 0.0512 (4)
H15 −0.101568 0.245152 1.100121 0.061*
C16 0.3811 (2) −0.10682 (15) 0.99030 (16) 0.0699 (5)
H16A 0.433419 −0.132876 0.927947 0.105*
H16B 0.324385 −0.162707 1.018537 0.105*
H16C 0.456381 −0.092731 1.035575 0.105*
O2 0.76343 (14) 0.99833 (9) 0.51039 (8) 0.0572 (3)
N5 0.69815 (13) 0.58124 (10) 0.99306 (8) 0.0399 (3)
N6 0.61966 (16) 0.63438 (12) 1.07473 (9) 0.0536 (4)
N7 0.80753 (15) 0.49468 (11) 1.12173 (9) 0.0498 (3)
N8 0.57036 (14) 0.73578 (10) 0.60405 (9) 0.0434 (3)
C17 0.69104 (19) 0.57859 (14) 1.14853 (11) 0.0524 (4)
H17 0.662799 0.596012 1.215117 0.063*
C18 0.80763 (17) 0.49931 (12) 1.02367 (11) 0.0445 (3)
H18 0.875191 0.451688 0.981055 0.053*
C19 0.66554 (16) 0.61822 (11) 0.89346 (10) 0.0382 (3)
C20 0.51301 (16) 0.64523 (12) 0.86690 (11) 0.0443 (3)
H20 0.431246 0.638520 0.913478 0.053*
C21 0.48263 (17) 0.68229 (13) 0.77066 (11) 0.0459 (4)
H21 0.380355 0.699114 0.752247 0.055*
C22 0.60497 (16) 0.69440 (11) 0.70147 (10) 0.0392 (3)
C23 0.75728 (17) 0.66234 (13) 0.72837 (11) 0.0482 (4)
H23 0.839374 0.666248 0.681307 0.058*
C24 0.78847 (17) 0.62467 (13) 0.82426 (11) 0.0471 (4)
H24 0.890678 0.603978 0.841884 0.057*
C25 0.64573 (17) 0.81053 (12) 0.56838 (10) 0.0429 (3)
H25 0.713999 0.837717 0.608494 0.052*
C26 0.62945 (16) 0.85561 (12) 0.46666 (10) 0.0415 (3)
C27 0.69152 (16) 0.95216 (12) 0.43840 (11) 0.0438 (3)
C28 0.67620 (19) 0.99467 (14) 0.34148 (12) 0.0535 (4)
H28 0.717174 1.058592 0.322274 0.064*
C29 0.6003 (2) 0.94185 (15) 0.27416 (12) 0.0588 (4)
H29 0.589952 0.971102 0.209862 0.071*
C30 0.5393 (2) 0.84654 (15) 0.30033 (12) 0.0550 (4)
H30 0.488981 0.811300 0.254207 0.066*
C31 0.55441 (18) 0.80413 (13) 0.39658 (11) 0.0479 (4)
H31 0.513495 0.739874 0.414714 0.057*
C32 0.8181 (2) 1.10139 (15) 0.48802 (15) 0.0649 (5)
H32A 0.902209 1.089249 0.437583 0.097*
H32B 0.854169 1.129090 0.547328 0.097*
H32C 0.734787 1.155112 0.464111 0.097*

Source of material

All chemicals were purchased from commercial sources and used as received without further purification. Under stirring, 4-[1,2,4]triazol-1-yl-phenylamine (4.00 mmol, 0.64 g) was added to a solution of 2-methoxy-benzaldehyde (6.98 mmol, 0.95 g) in ethanol (30 mL) in a 150 mL round bottom flask. The mixture was refluxed for 5 h, and then the precipitate was collected by filtration and washed with ethanol. The product was recrystallized from methanol to afford white crystal. Yield: 0.86 g (77.34%). m.p.: 212.1–212.4 °C. 1 H-NMR (CDCl3, 400 MHz, ppm): δ 8.96 (s, 1H), 8.56 (s, 1H), 8.16 (dd, J = 7.72 Hz, 1.76 Hz, 1H), 8.12 (s, 1H), 7.69 (dt, J = 9.48 Hz, 2.81 Hz, 2H), 7.48 (td, J = 7.90 Hz, 1.76 Hz, 1H), 7.35 (dt, J = 9.52 Hz, 2.81 Hz, 2H), 7.07 (t, J = 7.56 Hz, 1H), 6.98 (d, J = 8.36 Hz, 1H), 3.92 (s, 3H).

Experimental details

All H-atoms bonded to C atoms were placed geometrically and refined using a riding model with common isotropic displacement factors Uiso(H) = 1.2 or 1.5Ueq(parent C-atom).

Comment

1,2,4-triazol-based compounds received notable interest because of their prominent photophysical and chemical properties, and excellent biological activities, and have wide applications in the fields of biology, agriculture, pharmacy, and functional materials, and so on [4], [5], [6], [7]. The title compound was synthesized by a standard aldehyde-amine condensation reaction to give the Schiff base [8], [9], [10]. Furthermore, the title compound is an excellent N-containing ligand.

As shown in the figure, the title compound shows an E configuration in both crystallographically independent molecule with respect to the C=N bond, and the C=N bond lengths are 1.271 (N4=C9) and 1.272 (N8=C25) Å, which are shorter than the normal C=N bond length (1.34–1.38 Å). The C9–C10 and C25–C26 bond lengths are 1.469 and 1.466 Å, respectively. The N4–C6 and N8–C22 bond lengths are 1.422 and 1.423 Å, respectively. According to the X-ray diffraction analysis, there is partially delocalized electron and significant conjugation in the title compound. All geometric parameters are in the expected ranges [11].


Corresponding author: Lufei Xiao, School of Food and Environmental Engineering, Chuzhou Polytechnic, Chuzhou, Anhui 239000, China, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was supported by the foundation Programs as follows: Natural Science Research Program under Anhui Provincial Department of Education (KJ2017ZD49, KJ2018A0842, KJ2019A0545); National and Anhui College Student Innovation and Entrepreneurship Program (202110371010, S202010371057); The Ministry of Education Industry-University Cooperation Collaborative Education Project (202101052045).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

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Received: 2021-12-17
Accepted: 2022-01-18
Published Online: 2022-01-31
Published in Print: 2022-04-26

© 2022 Jie Liu et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
  4. The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
  5. Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
  6. Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
  7. Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
  8. The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
  9. Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
  10. The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
  11. The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
  12. Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
  13. The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
  14. Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
  15. The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
  16. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
  17. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
  18. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
  19. Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
  20. Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
  21. The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
  22. The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
  23. The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
  24. The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
  25. Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
  26. The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
  27. The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
  28. Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
  29. The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
  30. Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
  31. The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
  32. The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
  33. The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
  34. Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
  35. The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
  36. The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
  37. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
  38. Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
  39. Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
  40. Crystal structure of a second modification of Pachypodol, C18H16O7
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  42. The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
  43. The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
  44. The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
  45. Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
  46. The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
  47. Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
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