Startseite Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione – methanol (1/1), C11H13N5S
Artikel Open Access

Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione – methanol (1/1), C11H13N5S

  • Huijuan Jia , Zhen Dong , Xiaoyan Qin , Yiying Song , Zhibin Zhou und Caixia Yuan ORCID logo EMAIL logo
Veröffentlicht/Copyright: 16. März 2022

Abstract

C11H13N5S, monoclinic, P21/c (no. 14), a = 7.2720(14) Å, b = 11.631(2) Å, c = 17.031(3) Å, β = 95.12(3)°, V = 1434.7(5) Å3, Z = 4, R gt (F) = 0.0353, wR ref (F 2) = 0.0953, T = 293 K.

CCDC no.: 2142563

The molecular 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: 0.28 × 0.26 × 0.23 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.23 mm−1
Diffractometer, scan mode: Bruker APEX-II, ω
θ max, completeness: 30.8°, 99%
N(hkl)measured, N(hkl)unique, R int: 7771, 4368, 0.016
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 4127
N(param)refined: 174
Programs: Bruker [1], SHELX [2, 3]
Table 2:

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

Atom x y z U iso*/U eq
S1 0.78422 (3) −0.24333 (2) 0.01370 (2) 0.01791 (7)
N1 0.84375 (11) 0.02557 (7) 0.08601 (4) 0.01555 (15)
N2 0.75444 (10) −0.00422 (7) 0.01292 (4) 0.01410 (14)
N3 0.64332 (11) 0.03174 (7) −0.10979 (4) 0.01610 (15)
N4 0.66094 (11) −0.08516 (7) −0.09595 (4) 0.01603 (15)
H4 0.6293 −0.1362 −0.1311 0.019*
N5 0.88942 (12) −0.10133 (7) 0.27665 (5) 0.01809 (15)
C1 0.65262 (18) 0.40477 (9) −0.08053 (7) 0.0287 (2)
H1A 0.5513 0.4144 −0.0486 0.043*
H1B 0.6294 0.4481 −0.1284 0.043*
H1C 0.7642 0.4318 −0.0521 0.043*
C2 0.67312 (14) 0.27784 (9) −0.10033 (5) 0.01984 (18)
H2A 0.7740 0.2684 −0.1334 0.024*
H2B 0.5609 0.2510 −0.1297 0.024*
C3 0.71077 (12) 0.20526 (8) −0.02574 (5) 0.01575 (16)
H3A 0.8318 0.2244 −0.0006 0.019*
H3B 0.6201 0.2238 0.0108 0.019*
C4 0.70318 (11) 0.07964 (8) −0.04300 (5) 0.01406 (15)
C5 0.73196 (12) −0.11172 (8) −0.02254 (5) 0.01472 (15)
C6 0.81785 (12) −0.04320 (8) 0.14315 (5) 0.01588 (16)
H6 0.7380 −0.1054 0.1355 0.019*
C7 0.91716 (12) −0.02152 (8) 0.22116 (5) 0.01482 (16)
C8 1.03382 (13) 0.07302 (8) 0.23567 (5) 0.01854 (17)
H8 1.0475 0.1273 0.1965 0.022*
C9 1.12899 (15) 0.08451 (9) 0.30973 (6) 0.02275 (19)
H9 1.2075 0.1466 0.3211 0.027*
C10 1.10449 (14) 0.00133 (10) 0.36662 (5) 0.0230 (2)
H10 1.1682 0.0061 0.4164 0.028*
C11 0.98324 (15) −0.08899 (9) 0.34785 (5) 0.02172 (19)
H11 0.9662 −0.1436 0.3864 0.026*
O1 0.41055 (10) 0.24531 (6) 0.21332 (4) 0.01865 (14)
H1 0.3233 0.2881 0.2193 0.028*
C12 0.56624 (15) 0.31240 (10) 0.19461 (6) 0.0249 (2)
H12A 0.5914 0.3706 0.2341 0.037*
H12B 0.5394 0.3481 0.1441 0.037*
H12C 0.6721 0.2634 0.1932 0.037*

Source of material

About 5 mmol of 4-amino-3-ethyl-1,2,4-triazole-5-thione solid was completely dissolved in 10 mL methanol solution in a 50 mL round-bottom flask, and then 5 mmol of yellowish pyridine formaldehyde solution was gradually added to the above mixed solution. After the mixture was stirred and refluxed for 3.5 h, and cooled to room temperature, the yellowish precipitate was collected by vacuum filtration, and recrystallized from methanol, and finally dried in vacuo. Yield 89%. In addition, the yellow crystal was precipitated from the filtrate that had been left standing for two weeks. Elemental analysis calculated for C11H13N5S: Calcd(%) C 53.42; H 5.30; N 28.32; Found(%) C 53.28; H 5.23; N 28.21; IR(cm−1): 3429, 1589, 1413, 1315, 999, 758; UV(nm): 333, 244, 206.

Experimental details

The structures were solved by the direct method. Hydrogen atoms attached to C, N, and O atoms were constrained using a riding model approximation, with C–H = 0.93–0.97 Å, O–H = 0.82 Å, and U iso(H) = 1.2U eq(C).

Comment

Aromatic heterocycles such as 1,2,4-triazole, imidazole, pyridine, pyrazine, quinoline as well as their derivatives are arguably the most facile and widely used ligands in coordination chemistry [4], [5], [6], [7]. Of them, 1,2,4-triazole rings have been combined with pyridine rings to prepare bi and tridentate ligands [8, 9]. The simplest addition of a 1,2,4-triazole unit at a pyridine ring is the formation of the Schiff base compound. A number of N-heterocyclic Schiff base compounds have received much attention not only in the crystal engineering of coordination polymers [10], but also in the other fields [11], [12], [13]. In the course of our previous work, some 1,2,4-triazole derivative Schiff base ligands and their metal complexes have been development [6, 7, 14, 15]. As a part of our continuing investigation on complexes derived from different N-donor Schiff base ligands, herein we reported the structure of a new Schiff base. The title compound was characterized by Fourier transform IR spectroscopy, UV–vis spectroscopy, elemental analysis and X-ray diffraction.

The asymmetric unit of the title complex contains one target molecule and one methanol molecules. The title molecule is shown in the figure. All bond lengths and angles are in the expected ranges. Of them, the bond length of the C=S (1.682 Å) is close to the typical C=S double bond (1.646 Å) [16], which indicates that the thione form exists in the compound. In the molecule, the dihedral angle between the triazole and pyridine moiety is 34.43°. This twist is different from the reported 1,2,4-triazole derivative compound (4-[(5-bromo-2-hydroxybenzylidene) amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione and 4-[(5-chloro-2-hydroxybenzylidene) amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione) [6, 14]. In addition, there are intermolecular hydrogen bonds and weak ππ interactions in the structure. The title compound and methanol molecules were linked together through N4–H4⃛O1 i (i = 1−x, −1/2−y, 1/2−z) and O1 i –H1 i ⃛N5 ii (ii = x, −1/2−y, 1/2+z) to form a chain structure. The geometry analysis shows a face-to-face alignment of the aromatic-aromatic rings, and the centroid distances of Cg1 ring (N2–C4–N3–N4–C5) and Cg1 ii (ii = 1−x, −y, −z) ring is 3.5413(9) Å.


Corresponding author: Caixia Yuan, Institute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of the Education Ministry, Shanxi University, Taiyuan, Shanxi, 030006, People’s Republic of China, E-mail:

Funding source: Natural Science Foundation of Shanxi Province http://dx.doi.org/10.13039/501100004480

Award Identifier / Grant number: 201901D111014

Funding source: Shanxi Scholarship Council of China

Award Identifier / Grant number: 2020-001

Award Identifier / Grant number: http://dx.doi.org/10.13039/501100003398

Funding source: Project 2021019342 Supported by Shanxi University's Training Program of Innovation and Entrepreneurship for Undergraduates

Award Identifier / Grant number: 2021019342

  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 Natural Science Foundation of Shanxi Province (201901D111014), Research Project Supported by Shanxi Scholarship Council of China (2020-001) and Project 2021019342 supported by Shanxi University's Training Program of Innovation and Entrepreneurship for Undergraduates.

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

References

1. Bruker. SMART and SAINT; Bruker AXS Inc.: Madison, WI, USA, 2007.Suche in Google Scholar

2. Sheldrick, G. M. SHELXTL – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Suche in Google Scholar

3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Suche in Google Scholar

4. Klingele, M. H., Brooker, S. Synthesis and X-ray crystal structure of a polymeric copper(II) complex containing the novel ligand 4,40-(1,4-phenylene)bis[3-phenyl-5-(2-pyridyl)-4H-1,2,4-triazole]. Inorg. Chim. Acta. 2004, 357, 1598–1602; https://doi.org/10.1016/j.ica.2003.11.018.Suche in Google Scholar

5. Zabiulla Al-Ostoot, F. H., Asha, M. S., Al-Ghorbani, M., Khanum, S. A. Recent investigation on heterocycles with one nitrogen [piperidine, pyridine and quinoline], two nitrogen [1,3,4-thiadiazole and pyrazole] and three nitrogen [1,2,4-triazole]: a review. J. Iran. Chem. Soc. 2022, 19, 23–54; https://doi.org/10.1007/s13738-021-02293-x.Suche in Google Scholar

6. Niu, M. Y., Yuan, C. X. Crystal structure of 4-[(5-chloro-2-hydroxybenzylidene)amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione, C12H13ClN4OS. Z. Kristallogr. NCS 2021, 236, 643–645; https://doi.org/10.1515/ncrs-2021-0020.Suche in Google Scholar

7. Wang, J. W., Li, X. H., Yuan, C. X., Su, F., Wu, Y. B., Lu, L. P., Zhu, M. L., Xing, S., Fu, X. Q. Syntheses, crystal structures, and biological evaluations of new dinuclear platinum(II) complexes with 1,2,4-triazole derivatives as bridging ligands. Dalton Trans. 2021, 50, 4527–4538; https://doi.org/10.1039/d0dt03285a.Suche in Google Scholar

8. Jindabot, S., Teerachanan, K., Thongkam, P., Kiatisevi, S., Khamnaen, T., Phiriyawirut, P., Charoenchaidet, S., Sooksimuang, T., Kongsaeree, P., Sangtrirutnugul, P. Palladium(II) complexes featuring bidentate pyridineetriazole ligands: synthesis, structures, and catalytic activities for Suzukie Miyaura coupling reactions. J. Organomet. Chem. 2014, 750, 35–40; https://doi.org/10.1016/j.jorganchem.2013.10.046.Suche in Google Scholar

9. Guino-o, M. A., Folstad, M. J., Janzen, D. E. Crystal structures of 2,6-bis[(1H-1,2,4-triazol-1-yl)-methyl]pyridine and 1,1-[pyridine-2,6-diylbis-(methylene)]bis(4-methyl-1H-1,2,4-triazol-4-ium) iodide triiodide. Acta Crystallogr. 2015, E71, 128–132; https://doi.org/10.1107/s2056989014027881.Suche in Google Scholar

10. Ei-Kurdi, S., Thaher, B. A., Wahedy, K., Scholleyer, D., Nopper, L., Riester, O., Deigner, H. P. Efficient synthesis and X-ray structure of [1,2,4]triazolo[4,3-a]pyridines via oxidative cyclization using N-chlorosuccinimide (NCS). Crystals 2021, 11, 1156–1163.10.3390/cryst11101156Suche in Google Scholar

11. Ceylan, S. Synthesis and biological evaluation of new Mannich and Schiff bases containing 1,2,4-triazole and 1,3,4-oxadiazole nucleus. Med. Chem. Res. 2016, 25, 1958–1970; https://doi.org/10.1007/s00044-016-1640-9.Suche in Google Scholar

12. Alaghaz, A. M. A., Zayed, M. E., Alharbi, S. A., Ammar, R. A. A., Chinnathambi, A. Synthesis, spectroscopic identification, thermal, potentiometric and antibacterial activity studies of 4-amino-5-mercapto-S-triazole Schiff base complexes. J. Mol. Struct. 2015, 1087, 60–67; https://doi.org/10.1016/j.molstruc.2015.01.035.Suche in Google Scholar

13. Dang, D. B., Li, M. M., Bai, Y., Ning, R. Q. Two Cd(II) coordination polymers based on asymmetrical Schiff-base ligand with five- and six-membered N-containing heterocyclic rings: synthesis, crystal structures and luminescent properties. Synth. Met. 2012, 162, 2075–2080; https://doi.org/10.1016/j.synthmet.2012.09.023.Suche in Google Scholar

14. Yuan, C. X., Yao, X. M., Zhu, M. L., Zhu, H. M. 4-[(5-Chloro-2-hydroxybenzylidene)-amino]-3-ethyl-1H-1,2,4-triazole-5(4H)-thione. Acta Crystallogr. 2014, E70, o574–o575; https://doi.org/10.1107/s1600536814008320.Suche in Google Scholar

15. Wu, X., Yuan, C. X., Ma, L., Zhai, K. L., Zhu, M. L. 4-[(5-Bromo-2-hydroxybenzylidene)amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione. Acta Crystallogr. 2012, E68, o1674; https://doi.org/10.1107/s1600536812019745.Suche in Google Scholar

16. Fuyita, E., Nagao, Y., Seno, K. I., Takano, S., Miyasaka, T., Kimura, M., Watson, W. H. Studies on the structure of some derivatives of 1,3-triazolidine-2-thione and Δ2-1,3-thiazoline-2-thiol. J. Chem. Soc., Perkin Trans. 1981, 1, 914–919.10.1039/P19810000914Suche in Google Scholar

Received: 2022-01-22
Accepted: 2022-03-07
Published Online: 2022-03-16
Published in Print: 2022-06-27

© 2022 Huijuan Jia 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 (E)-(4-imidazol-1-yl-phenyl)-(2-methoxy-benzylidene)-amine monohydrate, C17H17N3O2
  4. Crystal structure of 6-methyl-3-(pyrrolidine-1-carbonyl)-2H-chromen-2-one, C15H15N1O3
  5. Crystal structure of 4-methyl-4-nitropentanoic acid, C6H11NO4
  6. The crystal structure of (E)-3-(furan-2-yl)acrylonitrile, C7H5NO
  7. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)-1H-pyrazole-4-carboxamide monohydrate, C23H26F2N4O3
  8. Crystal structure of 2-(4-bromobenzyloxy)-6-chloropyridine, C12H9BrClNO
  9. Crystal structure of N-(4-bromo-2,6-dichloro-phenyl)pyrazin-2-amine, C10H6BrCl2N3
  10. Crystal structure of (E)-1-(2–nitrophenyl)-3-phenylprop-2-en-1-one, C15H11NO3
  11. The crystal structure of (E)-3-chloro-2-(2-(4-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  12. Crystal structure of (E)-amino(2-(thiazol-2-ylmethylene)hydrazineyl)methaniminium nitrate, C10H16N12O6S2
  13. Crystal structure of 9-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C15H18N4O
  14. The crystal structure bis(dimethylsulfoxide-κ1O)-dipyridine-κ1 N-bis(m2-(Z)-3-methyl-2-oxido-N-((Z)-oxido(phenyl)methylene)benzohydrazonato-κ5)trinickel(II) - dimethylsulfoxide (1/2), C48H56N6Ni3O10S4
  15. Crystal structure of bis(bis(triphenylphosphine)iminium) tetradecacarbonyltetratelluridopentaferrate(2-), (PPN)2[Fe5Te4(CO)14]
  16. Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one, C15H14O2S
  17. The crystal structure of [(1,10-phenanthroline-κ2 N,N)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)nickel(II)] monohydrate, C36H26N4O5Ni
  18. Crystal structure of 3,3′-(pyridine-2,6-diylbis(methylene))bis(1-propyl-1H-imidazol-3-ium) ditetrafluoroborate, C19H27B2F8N5
  19. The crystal structure of (E)-1-(4-aminophenyl)-3-(p-tolyl)prop-2-en-1-one, C16H15NO
  20. The crystal structure of poly[(μ2-terephthalato-κ4O,O′: O″,O‴)-(μ4-terephthalato-κ4O:O′:O″:O‴)-{μ4-(1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ4O:O′:O″,O‴)}dicadmium(II)] – water – acetronitrile (1/2/2), C38H36N14O10Cd2
  21. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)cobalt(II)–water–N,N-dimethylformamide(1/2/1), C27H31N3O9Co
  22. The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid – 4,4′-bipyridine, C8H8O4·C10H8N2
  23. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)cobalt(II)], C32H22Br2CoN4O4
  24. Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione – methanol (1/1), C11H13N5S
  25. The crystal structure of (Z)-4-bromo-6-(((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)methylene)cyclohexa-2,4-dien-1-one monohydrate, C11H16BrNO5
  26. Crystal structure of bis(tetrapropylammonium) nonaselenidotetrastannate(IV), (Pr4N)2[Sn4Se9]
  27. Crystal structure of 2,6-di-tert-butyl-4-(4-chlorobenzylidene)cyclohexa-2,5-dien-1-one, C21H25ClO
  28. Crystal structure of (2,2′-((naphthalen-1-ylmethyl)azanediyl)diacetato-κ3 N,O,O′)-(1,10-phenanthroline-κ2 N,N′)-copper(II) trihydrate, CuC27H27N3O7
  29. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylato-κ2N,O)-bis(1H-pyrazol-3-ylamine-κ2 N:N)dicobalt(II) dihydrate, C27H23N5O5Co
  30. The crystal structure of bis((E)-2-((tert-butylimino)methyl)-4-chlorophenolato-κ2N,O)zinc(II), C22H26Cl2N2O2Zn
  31. The crystal structure of poly[diaqua-(μ3-5-nitrobenzene-1,2,3-tricarboxylato-κ3O:O′:O′)-(μ2-4,4′-dipyridylamine-κ2N:N′)copper(II)], C38H30Cu3N8O20
  32. The crystal structure of (E)-1-ferrocenyl-3-(naphthalen-1-yl)prop-2-en-1-one, C23H18FeO
  33. The crystal structure of (E)-1-ferrocenyl-3-(4-isopropylphenyl)prop-2-en-1-one, C22H22FeO
  34. Crystal structure of 6-hydroxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one, C10H10O4
  35. The crystal structure of (2E,4E)-1-ferrocenyl-5-phenylpenta-2,4-dien-1-one, C21H18FeO
  36. Crystal structure of alaninato-κ2N,O-bis(hydroxylamido-κ2N,O)-oxido-vanadium(V), C3H10N3O5V
  37. Crystal structure of catena-poly[aqua-bis[μ2-6-(1H-imidazol-1-yl)nicotinato-κ2 N,O]copper(II)], C18H14N6O5Cu
  38. Crystal structure of diethyl 4,6-diphenyl-1,9-di-p-tolylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,5(2H)-dicarboxylate, C42H42N2O4
  39. The crystal structure of cobalt cadmium bis(hydrogenphosphate) bis(phosphate(V)) tetrahydrate, H10O20P4Co3.14Cd1.86
  40. Crystal structure of dimethyl 1,4,6,9-tetraphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,7(2H)-dicarboxylate, C38H34N2O4
  41. Crystal structure of (Z)-4-(furan-2-yl((4-iodophenyl)amino)methylene)-5-methyl-2(p-tolyl)-2,4-dihydro-3H-pyrazol-3-one, C21H16I N3O2
  42. Crystal structure of (E)-1-(4-(3,5-dimethoxystyryl)phenyl)-7-ethylheptanedioate, C25H30O6
  43. Crystal structure of 6-bromo-2-(4-chlorophenyl)chroman-4-one (6-bromo-4′-chloroflavanone), C15H10BrClO2
  44. The crystal structure of 2-(benzhydryloxy)-3-nitropyridine, C18H14N2O3
  45. The crystal structure of 1,3(4,1)-dipyridin-1-iuma-2(1,8)-diethynylanthracena-5(1,3)-benzenacyclohexaphane-11,31-diium bis(hexafluoridophosphate), C36H24F12N2P2
  46. Crystal structure of 3,6-di-tert-butyl-1-iodo-9-methyl-8-(pyren-1-ylethynyl)-9H-carbazole, C39H34IN
  47. The cocrystal 2-(dimethylammonio)-5-nitrobenzoate – 2-(dimethylamino)-5-nitrobenzoic acid, C9H10N2O4
  48. Crystal structure of 5-nitroquinazolin-4(3H)-one, C8H5N3O3
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