Home Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
Article Open Access

Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S

  • Guo-Xiang Sun ORCID logo EMAIL logo , Li-Jing Min , Liang Han and Xing-Hai Liu
Published/Copyright: January 4, 2022
Download Article (PDF)
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 2

Abstract

C15H11N5S, orthorhombic, Pbca (no. 61), a = 9.7864(2) Å, b = 15.5709(3) Å, c = 18.7774(4) Å, V = 2861.36(10) Å3, Z = 8, R gt (F) = 0.0485, wR ref (F2) = 0.1390, T = 296.15 K.

CCDC no.: 2129573

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: Colorless block
Size: 0.26 × 0.24 × 0.22 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.23 mm−1
Diffractometer, scan mode: Bruker P4, ω
θmax, completeness: 27.5°, >99%
N(hkl)measured, N(hkl)unique, Rint: 14,104, 3291, 0.064
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1834
N(param)refined: 190
Programs: Bruker [1], Olex2 [2], SHELX [3, 4]
Table 2:

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

Atom x y z Uiso*/Ueq
S1 0.54434 (7) 0.12148 (5) 0.40264 (3) 0.0688 (3)
N1 0.3033 (3) 0.1055 (3) 0.25373 (14) 0.1320 (13)
N2 0.32293 (19) 0.02297 (11) 0.43785 (10) 0.0515 (5)
N3 0.22525 (19) 0.02069 (11) 0.49174 (10) 0.0504 (5)
N4 0.37085 (17) 0.12470 (10) 0.51578 (9) 0.0429 (4)
N5 0.0041 (3) 0.12568 (15) 0.72022 (13) 0.0803 (7)
C1 0.3958 (3) 0.0839 (2) 0.28496 (15) 0.0885 (10)
C2 0.5152 (3) 0.0572 (2) 0.32430 (14) 0.0807 (9)
H2A 0.5946 0.0609 0.2935 0.097*
H2B 0.5044 −0.0024 0.3383 0.097*
C3 0.4067 (2) 0.08598 (14) 0.45343 (11) 0.0454 (5)
C4 0.2550 (2) 0.08174 (13) 0.53737 (11) 0.0430 (5)
C5 0.1721 (2) 0.09991 (13) 0.60097 (10) 0.0447 (5)
C6 0.0341 (2) 0.07890 (15) 0.59960 (12) 0.0530 (6)
H6 −0.0052 0.0562 0.5586 0.064*
C7 −0.0432 (3) 0.09219 (17) 0.65951 (14) 0.0681 (7)
H7 −0.1350 0.0768 0.6578 0.082*
C8 0.1367 (3) 0.14596 (19) 0.71986 (14) 0.0786 (8)
H8 0.1728 0.1701 0.7611 0.094*
C9 0.2244 (3) 0.13394 (15) 0.66338 (12) 0.0608 (7)
H9 0.3163 0.1483 0.6671 0.073*
C10 0.4384 (2) 0.19786 (13) 0.54776 (10) 0.0410 (5)
C11 0.3701 (2) 0.27510 (14) 0.55115 (12) 0.0520 (6)
H11 0.2827 0.2805 0.5322 0.062*
C12 0.4333 (3) 0.34446 (15) 0.58314 (13) 0.0591 (6)
H12 0.3879 0.3968 0.5864 0.071*
C13 0.5623 (3) 0.33623 (15) 0.60991 (12) 0.0559 (6)
H13 0.6039 0.3830 0.6319 0.067*
C14 0.6316 (2) 0.25930 (15) 0.60474 (12) 0.0546 (6)
H14 0.7205 0.2549 0.6219 0.066*
C15 0.5691 (2) 0.18888 (14) 0.57408 (11) 0.0467 (5)
H15 0.6144 0.1365 0.5712 0.056*

Source of material

A mixture of isonicotinohydrazide (1.37 g, 10 mmol) and isothiocyanatobenzene (1.35 g, 10 mmol) in ethanol (50 mL) was refluxed for 5 h. After cooling, the 2-isonicotinoyl-N-phenylhydrazine-1-carbothioamide were obtained from the solution of ethanol. Then the 2-isonicotinoyl-N-phenylhydrazine-1-carbothioamide was dissolved in NaOH solution (5 mL, 2 mol/L) and refluxed for 4 h. After cooling, a hydrochloric acid solution (4 mol/L) was added dropwise. A large amount of solid (4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol) was obtained. Finally, N,N-dimethylformamide (DMF) (5 mL), a mixture of 4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol (0.25 g, 1 mmol), 2-chloroacetonitrile (1.1 mmol) and NaOH (0.05 g, 1.2 mmol) was stirred overnight. The mixture was poured into ice (40 mL) and the product precipitated. The crude product was recrystallized from EtOH to give colorless crystals after three days [5].

Experimental details

Using Olex2 [2], the structure was solved with the ShelXS [3] structure solution program using Direct Methods and refined with the ShelXL [4] refinement package Uiso values of the hydrogen atoms were set to 1.2 Ueq of the parent atoms.

Comment

1,2,4-Triazole compounds are attractive because of their excellent biological activity [6], [7], [8]. A pyridinyl substituted 1,2,4-triazole possessed diversity biological activities, such as antimicrobial activity [9] and there are related compounds that show fungicidal activity [10].

There is One molecule in the asymmetric unit (see the Figure). The bond angles and bond lengths of the title compound (pyridine ring, 1,2,4-triazole ring and phenyl ring) are all in the normal ranges [11–13]. The C–N bond length in the cyano group is 1.130(4) Å. The bond angle of C2–S1–C3 is 98.53(12)°, while the bond angle of N1–C1–C2 is 179.2(4)°. The torsion angle of the thioether group C1–C2–S1–C3 is 70.0(3)°. The plane of the triazole ring makes dihedral angles of 28.1° and 114.5° to the two other rings.

Corresponding author: Guo-Xiang Sun, School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng, 224051, Jiangsu, China, E-mail:

Funding source: Zhejiang Provincial Natural Science Foundation of China

Award Identifier / Grant number: LY19C140002

Award Identifier / Grant number: LY19B020009

Funding source: Chemical Company for Research

Award Identifier / Grant number: KYY-HX-20210140

Award Identifier / Grant number: KYY-HX-20190720

  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 funded by Zhejiang Provincial Natural Science Foundation of China (Nos. LY19C140002, LY19B020009), the Chemical Company for Research (KYY-HX-20210140, KYY-HX-20190720).

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

References

1. Bruker. SAINT, APEX2 and SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2009.Search in Google Scholar

2. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

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

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

5. Sun, G. X., Yang, M. Y., Shi, Y. X., Sun, Z. H., Liu, X. H., Wu, H. K., Li, B. J., Zhang, Y. G. Microwave assistant synthesis, antifungal activity and DFT theoretical study of some novel 1,2,4-triazole derivatives containing pyridine moiety. Int. J. Mol. Sci. 2014, 15, 8075–8090; https://doi.org/10.3390/ijms15058075.Search in Google Scholar PubMed PubMed Central

6. Zhang, Y. B., Liu, W., Yang, Y. S., Wang, X. L., Zhu, H. L., Bai, L. F., Qiu, X. Y. Synthesis, molecular modeling, and biological evaluation of 1,2,4-triazole derivatives containing pyridine as potential anti-tumor agents. Med. Chem. Res. 2012, 22, 3193–3203; https://doi.org/10.1007/s00044-012-0306-5.Search in Google Scholar

7. Shen, Z. H., Zhai, Z. W., Sun, Z. H., Weng, J. Q., Tan, C. X., Liu, X. H. Synthesis, crystal structure and biological activity of 2-chloro-5-(((5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-4-phenyl-4H-1,2,4-triazol-3-yl)thio)methyl)thiazole. Chin. J. Struct. Chem. 2017, 36, 1137–1141.Search in Google Scholar

8. Mazur, L., Koziol, A. E., Modzelewska-Banachiewicz, B., Ucherek, M., Zimecki, M., Artym, J. 2-(4-Phenyl-5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)cyclohexanecarboxylic acid and its DMSO solvate: synthesis, crystal structure and biological activity. J. Chem. Crystallogr. 2011, 41, 880–885; https://doi.org/10.1007/s10870-011-0017-7.Search in Google Scholar

9. Ahirwar, J., Ahirwar, D., Lanjhiyana, S., Jha, A. K., Dewangan, D., Badwaik, H. Synthesis, characterization, molecular modeling, and biological evaluation of 1,2,4-triazole-pyridine hybrids as potential antimicrobial agents. J. Heterocycl. Chem. 2018, 55, 2598–2609; https://doi.org/10.1002/jhet.3319.Search in Google Scholar

10. Yang, M. Y., Zhao, W., Liu, X. H., Tan, C. X., Weng, J. Q. Synthesis, crystal structure and antifungal activity of 4-(5-((2,4-dichlorobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)pyridine. Chin. J. Struct. Chem. 2015, 34, 203–207.Search in Google Scholar

11. Sun, G. X., Sun, Z. H., Yang, M. Y., Wu, H. K. Crystal structure of 4-(5-((2-methylbenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)pyridine, C21H18N4S. Z. Kristallogr. N. Cryst. Struct. 2016, 231, 1167–1168; https://doi.org/10.1515/ncrs-2016-0106.Search in Google Scholar

12. Mu, J. X., Zhai, Z. W., Yang, M. Y., Sun, Z. H., Wu, H. K., Liu, X. H. Synthesis, crystal structure, DFT study and antifungal activity of 4-(5-((4-bromobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)pyridine. Crystals 2016, 6, 4.10.3390/cryst6010004Search in Google Scholar

13. Sun, H., Zhang, L. Crystal structure of 2-(5-(pyridin-3-yl)-4-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)pyridine, C17H12N6. Z. Kristallogr. - N. Cryst. Struct. 2020, 235, 1161–1162, https://doi.org/10.1515/ncrs-2020-0223.Search in Google Scholar
Received: 2021-11-05
Accepted: 2021-12-17
Published Online: 2022-01-04
Published in Print: 2022-04-26

© 2021 Guo-Xiang Sun et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  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
  41. Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
  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
https://doi.org/10.1515/ncrs-2021-0431
Creative Commons
BY 4.0

Articles in the same Issue

  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
  41. Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
  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
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 21.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2021-0431/html
Scroll to top button