Home Crystal structure of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)(4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)methanone, C17H18F6N6O
Article Open Access

Crystal structure of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)(4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)methanone, C17H18F6N6O

  • Nian-Juan Pan , Chang Yan , Qiang Fei ORCID logo EMAIL logo and Wen-Neng Wu ORCID logo
Published/Copyright: August 1, 2023
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 238 Issue 5

Abstract

C17H18F6N6O, monoclinic, P21/n (no. 14), a = 9.9491(11) Å, b = 18.1523(17) Å, c = 11.7703(15) Å, β = 113.473(14)°, V = 1949.8(4) Å3, Z = 4, Rgt(F) = 0.0606, wRref(F2) = 0.1876, T = 169.99(10) K.

CCDC no.: 2282762

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: Colourless block
Size: 0.15 × 0.13 × 0.11 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.14 mm−1
Diffractometer, scan mode: SuperNova, ω
θmax, completeness: 25.0°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 7948, 3409, 0.052
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2543
N(param)refined: 278
Programs: Olex2 [1], Shelx [2, 3]
Table 2:

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

Atom x y z Uiso*/Ueq
F1 0.2465 (2) 0.51045 (11) −0.11940 (17) 0.0504 (5)
F2 0.24580 (19) 0.61700 (10) −0.04247 (18) 0.0522 (6)
F3 0.12910 (17) 0.52834 (11) −0.00436 (18) 0.0523 (6)
F4 0.7062 (2) 0.82670 (12) 0.69787 (19) 0.0599 (6)
F5 0.8248 (2) 0.89407 (10) 0.8558 (2) 0.0589 (6)
F6 0.6012 (2) 0.86766 (14) 0.8133 (3) 0.0855 (9)
O1 1.0177 (2) 0.75617 (11) 0.7954 (2) 0.0397 (6)
N1 0.4115 (2) 0.45207 (12) 0.1128 (2) 0.0292 (6)
N2 0.6078 (2) 0.48127 (12) 0.3068 (2) 0.0284 (6)
N3 0.6610 (3) 0.60361 (14) 0.3682 (2) 0.0318 (6)
N4 0.9274 (2) 0.64138 (12) 0.7422 (2) 0.0293 (6)
N5 0.7848 (3) 0.70002 (13) 1.0376 (2) 0.0368 (7)
N6 0.7239 (3) 0.76384 (13) 0.9829 (2) 0.0357 (6)
C1 0.3853 (3) 0.52515 (15) 0.0957 (3) 0.0268 (6)
C2 0.4649 (3) 0.57809 (15) 0.1748 (3) 0.0263 (6)
H2 0.445537 0.627914 0.157563 0.032*
C3 0.5787 (3) 0.55357 (15) 0.2848 (3) 0.0253 (6)
C4 0.5240 (3) 0.43438 (15) 0.2191 (3) 0.0285 (7)
C5 0.7685 (3) 0.58740 (15) 0.4919 (3) 0.0288 (6)
H5 0.805980 0.537410 0.492713 0.035*
C6 0.8961 (3) 0.64198 (16) 0.5253 (3) 0.0330 (7)
H6A 0.946610 0.634125 0.470772 0.040*
H6B 0.857985 0.691854 0.512488 0.040*
C7 1.0039 (3) 0.63324 (17) 0.6586 (3) 0.0320 (7)
H7A 1.049562 0.585058 0.669935 0.038*
H7B 1.080190 0.670224 0.678041 0.038*
C8 0.8122 (3) 0.58636 (15) 0.7195 (3) 0.0333 (7)
H8A 0.764903 0.594110 0.776438 0.040*
H8B 0.855022 0.537460 0.734036 0.040*
C9 0.6995 (3) 0.59187 (16) 0.5874 (3) 0.0317 (7)
H9A 0.647243 0.638177 0.577052 0.038*
H9B 0.628865 0.552307 0.572129 0.038*
C10 0.9399 (3) 0.70520 (14) 0.8037 (3) 0.0272 (6)
C11 0.8597 (3) 0.71327 (15) 0.8863 (3) 0.0304 (7)
C12 0.7713 (3) 0.77274 (15) 0.8935 (3) 0.0320 (7)
C13 0.8640 (3) 0.66829 (16) 0.9820 (3) 0.0344 (7)
H13 0.913321 0.623606 1.004146 0.041*
C14 0.7260 (3) 0.83939 (19) 0.8157 (3) 0.0459 (9)
C15 0.7510 (4) 0.67171 (19) 1.1392 (3) 0.0509 (9)
H15A 0.708849 0.710276 1.170267 0.076*
H15B 0.839309 0.654452 1.204384 0.076*
H15C 0.682554 0.631751 1.109862 0.076*
C16 0.5581 (3) 0.35447 (16) 0.2419 (3) 0.0413 (8)
H16A 0.569145 0.333180 0.171406 0.062*
H16B 0.479630 0.330232 0.254854 0.062*
H16C 0.647498 0.348494 0.313937 0.062*
C17 0.2527 (3) 0.54602 (16) −0.0180 (3) 0.0332 (7)
H3 0.631 (4) 0.652 (2) 0.360 (3) 0.057 (10)*

1 Source of materials

4-chloro-2-methyl-6-(trifluoromethyl)pyrimidine (10 mmol), and tert-butyl 4-aminopiperidine-1-carboxylate (8 mmol) were dissolved in isopropanol (10 mL). Then N,N-diisopropylethylamine (DIPEA, 10 mmol) was added slowly. The reaction was refluxed for 5 h. After completion, the reaction was cooled to room temperature, and dispersed with ethyl acetate. The solution was washed with distilled water (30 mL) for three times. The organic layers were collected and dried with anhydrous sodium sulfate. After filtering, the solvents were evaporated. The residue was purified by silica gel column chromatography. The obtained solid was deprotected in HCl/ethanol system to get 2-methyl-N-(piperidin-4-yl)-6-(trifluoromethyl)pyrimidin-4-amine. By using 2-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 1.5 mmol) as condensing agent, 2-methyl-N-(piperidin-4-yl)-6-(trifluoromethyl)pyrimidin-4-amine (1 mmol) was further reacted with 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (1 mmol) under DIPEA/DMF (2.5 mmol/10 mL) at room temperature. After completion, the distilled water was added to the reaction, and extracted with ethyl acetate for two times. The combined organic layers were further washed with ethyl acetate for five times. Then the solution was dried with anhydrous sodium sulfate. After filtering, the solvents were removed by rotary evaporation. The residue was purified by silica gel column chromatography to obtain a white solid. After slow volatilization of methanol at room temperature, colourless crystals of the title compound were obtained.

2 Experimental details

Coordinates of hydrogen atoms were set. Their Uiso values were set to 1.2Ueq of the parent atoms. Using Olex2 [1], the structure was solved with the Shelxt [2] structure solution program using and refined with the Shelxl [3] refinement package.

3 Comment

Pyrimidines are extensively presented in fungicides, such as Fenarimol, Mepanioyrim, and Pyrimethanil. Several pyrimidine compounds have been utilized to control plant fungal diseases [4], [5], [6], [7], [8], [9]. Pyrazole as a classical five-membered heterocyclic compound, has been an vital intermediate skeleton of agrochemicals [10], [11], [12]. Many compounds containing pyrazole [13, 14] or pyrimidine [15, 16] moiety were developed. Compared to the reported crystal [17], the title structure was constructed by linking pyrimidine and pyrazole with a bridge group of aminopiperidine [18]. The characteristic C–N bond length of aminopiperidine linked to pyrimidine and pyrazole are 1.348(4) Å (N3–C3) and 1.345(4) Å (N4–C10). The torsion angle of C5–N3–C3–N2 is −9.7(4)°, and the torsion angle of N4–C10–C11–C13 is 54.1(4)°. The dihedral angle between pyrimidine plane and pyrazole plane is 73.75(1)°. The piperidine ring is in a relatively stable chair configuration (cf. the Figure), and the bond angles of N3–C5–C6 and C10–N4–C7 are 109.2(2)° and 119.0(2)°. In addition, the characteristic bond angles in the three rings of N2–C4–N1, C13–N5–N6, and C8–N4–C7 are 126.6(2)°, 112.1(2)°, and 112.7(2)°, respectively. Intermolecular hydrogen bonding exists in the title crystal structure. The oxygen atom O1 provides intermolecular hydrogen bonds to fluoro atom F2 (O1–F2 = 3.424 Å), hydrogen atom H3(O1–H3 = 3.424 Å) and hydrogen atom H15A (O1–H15A = 3.424 Å).

Corresponding author: Qiang Fei, School of Food Science and Engineering, Guiyang University, Guiyang, Guizhou, China, E-mail:

Funding source: Guiyang University Graduate Project

Award Identifier / Grant number: GYU–YJS[2021]-33

Funding source: Guiyang University Initial Funding Project

Award Identifier / Grant number: GYU–ZRD[2018]-023

Funding source: Guizhou Provincial Science and Technology Projects

Award Identifier / Grant number: QKHPR–CXTD[2022]002

Funding source: Education Department of Guizhou Province-Natural Science Research Project

Award Identifier / Grant number: QJJ[2023]042

  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 Guiyang University Graduate Project (NO. GYU-YJS[2021]-33), Guiyang University Initial Funding Project (NO. GYU-ZRD[2018]-023), Guizhou Provincial Science and Technology Projects (NO. QKHPR-CXTD[2022]002), and Education Department of Guizhou Province-Natural Science Research Project (No. QJJ[2023]042).

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

References

1. 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

2. 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 PubMed PubMed Central

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. Wu, W. N., Jiang, Y. M., Fei, Q., Du, H. T. Synthesis and fungicidal activity of novel 1,2,4-triazole derivatives containing a pyrimidine moiety. Phosphorus, Sulfur, Silicon Relat. Elem. 2019, 194, 1171–1175; https://doi.org/10.1080/10426507.2019.1633321.Search in Google Scholar

5. Zhang, P., Guan, A., Xia, X., Sun, X., Wei, S., Yang, J., Wang, J., Li, Z., Lan, J., Liu, C. Design, synthesis, and structure-activity relationship of new arylpyrazole pyrimidine ether derivatives as fungicides. J. Agric. Food Chem. 2019, 67, 11893–11900; https://doi.org/10.1021/acs.jafc.9b05185.Search in Google Scholar PubMed

6. Hai, D. S., Ha, N., Tung, D. T., Giang, N., Huong, N., Anh, H. H., Van, H., Toan, D., Thanh, N. Synthesis, biological evaluation and induced fit docking simulation study of d-glucose-conjugated 1H-1,2,3-triazoles having 4H-pyrano[2,3-d]pyrimidine ring as potential agents against bacteria and fungi. New J. Chem. 2022, 46, 8303–8323; https://doi.org/10.1039/d1nj05330b.Search in Google Scholar

7. Desai, N. C., Vaghani, H. V., Jethawa, A. M., Khedkar, V. M. In silico molecular docking studies of oxadiazole and pyrimidine bearing heterocyclic compounds as potential antimicrobial agents. Arch. Pharm. 2021, 354, 2100134; https://doi.org/10.1002/ardp.202100134.Search in Google Scholar PubMed

8. Ghoneim, A. A., Bilel, H., Moustafa, S. M. N. Design, synthesis, and antifungal activity of some new thiazolo[4,5-d] pyrimidine-5-thione derivatives. Russ. J. Org. Chem. 2020, 56, 2148–2152; https://doi.org/10.1134/s1070428020120167.Search in Google Scholar

9. Blokhina, S. V., Sharapova, A. V., Ol’khovich, M. V., Doroshenko, I. A., Levshin, I. B., Perlovich, G. L. Synthesis and antifungal activity of new hybrids thiazolo[4,5-d]pyrimidines with (1H-1,2,4)triazole. Bioorg. Med. Chem. Lett. 2021, 40, 127944; https://doi.org/10.1016/j.bmcl.2021.127944.Search in Google Scholar PubMed

10. Xia, D. G., Cheng, X., Liu, X. H., Zhang, C. Q., Wang, Y. X., Liu, Q. Y., Zeng, Q., Huang, N. Q., Cheng, Y., Lv, X. H. Discovery of novel pyrazole carboxylate derivatives containing thiazole as potential fungicides. J. Agric. Food Chem. 2021, 69, 8358–8365; https://doi.org/10.1021/acs.jafc.1c01189.Search in Google Scholar PubMed

11. Halim, K. N. M., Ramadan, S. K., Rizk, S. A., EI-Hashash, M. A. Synthesis, DFT study, molecular docking and insecticidal evaluation of some pyrazole-based tetrahydropyrimidine derivatives. Synth. Commun. 2020, 50, 1159–1175; https://doi.org/10.1080/00397911.2020.1720739.Search in Google Scholar

12. Ahmed, W., Yan, X. J., Hu, D. K., Adnan, M., Tang, R. Y., Cui, Z. N. Synthesis and fungicidal activity of novel pyrazole derivatives containing 5-phenyl-2-furan. Bioorg. Med. Chem. 2019, 27, 115048; https://doi.org/10.1016/j.bmc.2019.115048.Search in Google Scholar PubMed

13. Wei, W., Wu, Q., Jin, T. Y., Zhang, Y. Z., Xuan, Z. K., Zhang, H. Q. Crystal structure of (Z)-4-[(p-tolylamino)(furan-2-yl) methylene]-3-phenyl-1-1-p-tolyl-1H-phenyl-1H-pyrazol-5(4H)-one, C28H23N3O2. Z. Kristallogr. N. Cryst. Struct. 2022, 237, 527–529; https://doi.org/10.1515/ncrs-2022-0086.Search in Google Scholar

14. Li, N., Li, Z., Wang, T. C., Miao, J., Wu, H. X., Gao, J. L., Shan, J. C. Crystal structure of N-2,6-difluorobenzoyl-N′-[1-(3-chloro-4-methyl-phenyl)-4-cyano-1H-pyrazol-5-carbamoyl]urea, C19H12ClF2N5O2. Z. Kristallogr. N. Cryst. Struct. 2023, 238, 193–195; https://doi.org/10.1515/ncrs-2022-0569.Search in Google Scholar

15. Shin, S. Y., Koh, D. The crystal structure of 2-(7-(2,3-dimethoxyphenyI)-[1,2,4]triazolo[1,5-a]-pyrimidin-5-yl)-3-methoxyphenol, C20H18N4O4. Z. Kristallogr. N. Cryst. Struct. 2023, 238, 167–169; https://doi.org/10.1515/ncrs-2022-0534.Search in Google Scholar

16. Lou, X. H. Crystal structure of 2-(2-(6-methylpyridin-2-yl)naphthalen-1-yD)pyrimidine, C20H15N3. Z. Kristallogr. N. Cryst. Struct. 2019, 234, 1037–1038; https://doi.org/10.1515/ncrs-2019-0247.Search in Google Scholar

17. Fang, B., Meng, J. P., Gan, L. L. Crystal structure of methyl 2-(4-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yI)pheny)acetate, C19H17N5O2. Z. Kristallogr. N. Cryst. Struct. 2019, 234, 575–577; https://doi.org/10.1515/ncrs-2018-0580.Search in Google Scholar

18. Yin, L., Zhang, M. X., He, T. G. Design and development of novel thiazole-sulfonamide derivatives as a protective agent against diabetic cataract in Wistar rats via inhibition of aldose reductase. Heterocycl. Commun. 2021, 27, 63–70; https://doi.org/10.1515/hc-2020-0124.Search in Google Scholar
Received: 2023-06-03
Accepted: 2023-07-19
Published Online: 2023-08-01
Published in Print: 2023-10-26

© 2023 the author(s), 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. The crystal structure of (N-([1,1′:4′,1″-terphenyl]-4,4′-diethyl)-2-(bis(pyridin-2-ylmethyl)amino)acetamide-κ4N,N,N″, O)tri(nitrato-kO, O′) samarium(III) - methanol - acetonitrile (1/1/1), C40H39SmN8O14
  4. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(2-chloro-4-methyl phenolate-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV), C27H27Cl2N3O6Ti
  5. N′-[(1E)-(4–Fluorophenyl)methylidene]adamantane-1-carbohydrazide, C18H21FN2O
  6. Crystal structure of 4-bromo-3-nitro-1H-pyrazole-5-carboxylic acid monohydrate, C4H2N3BrO4·H2O
  7. Crystal structure of dipyridine-k1N-tris(2,2,6,6-tetramethyl-5-oxohept-3-en-3-olato-k2O,O′)dysprosium(III), DyC43H67O6N2
  8. Crystal structure of cyclo[tetraiodido-bis{μ2-1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-isopropyl-imidazol)-k2N:N}dicadmiun(II)], C26H30N10Cd2I4
  9. The crystal structure of tert-butyl (E)-3-(2-(benzylideneamino)phenyl)-1H-indole-1-carboxylate, C26H24N2O2
  10. The crystal structure of 4-(3-carboxy-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4- dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 2,5-dihydroxybenzoate methanol solvate, C27H32FN3O9
  11. Crystal structure of (μ2-1-(4,4′-bipyridine-κ2N:N′)-bis[diaqua-(4-iodopyridine-2,6-dicarboxylato-κ3O,N,O′)–cobalt(II)], C24H20Co2I2N4O12
  12. The crystal structure of dimethyl 4,4′-(10,20-diphenylporphyrin-5,15-diyl)dibenzoate dichloromethane solvate, C49H36N4O4Cl2
  13. (E)-2-((E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ylidene)hydrazine-1-carbothioamide C14H23N3S1
  14. The crystal structure of [1-(4-(trifluoromethyl)phenyl)-3,4-dihydroquinolin-2(1H)-one], C16H12F3NO
  15. Crystal structure of (E)-2-amino-N′-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)benzohydrazide – dimethylformamide – water (1/1/2), C15H16N4O3·C3H7NO·2H2O
  16. Crystal structure of 3-(4-bromophenyl)-5-methyl-1H-pyrazole, C10H9BrN2
  17. Crystal structure of 1,10-phenanthrolinium bromide dihydrate, C12H9N2Br
  18. Crystal structure of N-(4′-chloro-[1,1′-biphenyl]-2-yl)formamide, C13H10ClNO
  19. The crystal structure of nitroterephthalic acid, C8H5NO6
  20. Crystal structure of (2-((4-bromo-2,6-dichlorophenyl)amino)phenyl) (morpholino)methanone, C17H15BrCl2N2O2
  21. Crystal structure of tetraaqua-bis(ethanol-κO)-tetrakis(μ2-trifluoroacetate-κ2O:O′)-bis(trifluoroacetate-κ2O)digadolinium(III) Gd2C16H20O18F18
  22. The crystal structure of dimethyl 4,4′-[10,20-bis(2,6-difluorophenyl)porphyrin-5,15-diyl]dibenzoate chloroform solvate, C50H32Cl6F4N4O4
  23. The crystal structure of N,N′-((nitroazanediyl)bis(methylene))diacetamide, C6H12O4N4
  24. The crystal structure of [bis(2,2′-bipyridine-6-carboxylato-κ3N,N,O)magnesium(II)]dihydrate, C22H18N4O6Mg
  25. Crystal structure of poly[diaqua-(bis(μ2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′] cobalt(II)-tetraqua-bis(1,4-bis(imidazol-1-ylmethyl)benzene)-κ1N)-cobalt(II) di(2,5-thiophenedicarboxylate) dihydrate, C68H76Co2N16O16S2
  26. Crystal structure of poly[chlorido-μ2-chlorido-(μ2-1-[(2-ethyl-4-methyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κN:N’)cadmium(II)], C13H15CdN5Cl2
  27. The crystal structure of (4-hydroxybenzenesulfonate)-k1O-6,6′-((1E,1′E)- (ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene)) bis(2-methoxyphenol)-κ2N,N,μ2O,O,κ2O, O)-(methanol)-cobalt(II) sodium(I), C25H27CoN2NaO9S
  28. Crystal structure of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)(4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)methanone, C17H18F6N6O
  29. Crystal structure of bis{[(cyclohexylimino)(phenylimino)-l5-(methyl)diethylazane-κ2N:N′]-(ethyl)-zinc(II)]}, C38H62N6Zn2
  30. Crystal structure of 2-[(4-bromobenzyl)thio]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C13H8Br2N2OS2
  31. Crystal structure of 10-methoxy-7,11b,12,13-tetrahydro-6H-pyrazino [2′,3′:5,6]pyrazino[2,1-a]isoquinoline, C15H16N4O
  32. The crystal structure of 1-propyl-2-nitro-imidazole oxide, C6H9N3O3
  33. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid–2-ethoxybenzamide (1/1), C17H16N2O8
  34. The structure of RUB-1, (C8H16N)6[B6Si48O108], a boron containing levyne-type zeolite, occluding N-methyl-quinuclidinium in the cage-like pores
  35. The crystal structure of diaqua-(naphthalene-4,5-dicarboxylate-1,8-dicarboxylic anhydride-κ1O)-(4′-(4-(1H-benzimidazolyl-1-yl)phenyl)-2,2′:6′,2″-terpyridine-κ3N,N′,N″)–manganese(II) dihydrate, C42H27MnN5O9·2H2O
  36. Crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene))bis (3-(3-bromopropoxy)phenol), C20H22Br2N2O4
  37. The crystal structure of 3-(2-hydroxyphenyl)-4-phenyl-6-(p-tolyl)-2H-pyran-2-one, C24H18O3
  38. Crystal structure of bis(μ2-2-(1,5-dimethyl–3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)-(nitrato-κ2O,O′)dicobalt(II), C36H32Co2N8O4
  39. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α] phenanthren-3-one O-(4-fluorobenzoyl) oxime, C28H36FNO2
  40. The crystal structure of 4-aminiumbiphenyl benzenesulfonate, C18H17NO3S
  41. Synthesis and crystal structure of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate, C18H17N3O9
  42. Crystal structure of N-(Ar)-N′-(Ar′)-formamidine, C14H12Br2N2O
  43. The crystal structure of 4-(2,4-dichlorophenyl)-2-(4-fluorophenyl)-5-methyl-1H-imidazole, C16H11Cl2FN2
  44. Crystal structure of 1-(4–chlorophenyl)-4-benzoyl-3-methyl-1H-pyrazol-5-ol, C17H13ClN2O2
  45. The crystal structure of 5-amino-1-methyl-4-nitroimidazole, C4H6O2N4
  46. Crystal structure of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene-N,N′-bis(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-1,3,2-diazaborol-2-yl)-l2-germenediamine, C63H94B2GeN8
  47. The crystal structure of (bromido, chlorido)-tricarbonyl-(5,5′-dimethyl-2,2′-bipyridine)-rhenium(I), C15H12Br0.2Cl0.8N2O3Re1
  48. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
  49. The crystal structure of poly[2-(4-carboxypyridin-3-yl)terephthalpoly[diaqua-(μ4-2-(6-carboxylatopyridin-3-yl)terephthalato-κ5O,N:O′:O″,O‴)]) cadmium(II)] dihydrate, C28H20Cd3N2O16
  50. Crystal structure of [tetraaqua-bis((3-carboxy-5-(pyridin-4-yl)benzoate-κ1N)cobalt(II)] tetrahydrate, C26H32CoN2O16
  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
https://doi.org/10.1515/ncrs-2023-0265
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of (N-([1,1′:4′,1″-terphenyl]-4,4′-diethyl)-2-(bis(pyridin-2-ylmethyl)amino)acetamide-κ4N,N,N″, O)tri(nitrato-kO, O′) samarium(III) - methanol - acetonitrile (1/1/1), C40H39SmN8O14
  4. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(2-chloro-4-methyl phenolate-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV), C27H27Cl2N3O6Ti
  5. N′-[(1E)-(4–Fluorophenyl)methylidene]adamantane-1-carbohydrazide, C18H21FN2O
  6. Crystal structure of 4-bromo-3-nitro-1H-pyrazole-5-carboxylic acid monohydrate, C4H2N3BrO4·H2O
  7. Crystal structure of dipyridine-k1N-tris(2,2,6,6-tetramethyl-5-oxohept-3-en-3-olato-k2O,O′)dysprosium(III), DyC43H67O6N2
  8. Crystal structure of cyclo[tetraiodido-bis{μ2-1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-isopropyl-imidazol)-k2N:N}dicadmiun(II)], C26H30N10Cd2I4
  9. The crystal structure of tert-butyl (E)-3-(2-(benzylideneamino)phenyl)-1H-indole-1-carboxylate, C26H24N2O2
  10. The crystal structure of 4-(3-carboxy-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4- dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 2,5-dihydroxybenzoate methanol solvate, C27H32FN3O9
  11. Crystal structure of (μ2-1-(4,4′-bipyridine-κ2N:N′)-bis[diaqua-(4-iodopyridine-2,6-dicarboxylato-κ3O,N,O′)–cobalt(II)], C24H20Co2I2N4O12
  12. The crystal structure of dimethyl 4,4′-(10,20-diphenylporphyrin-5,15-diyl)dibenzoate dichloromethane solvate, C49H36N4O4Cl2
  13. (E)-2-((E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ylidene)hydrazine-1-carbothioamide C14H23N3S1
  14. The crystal structure of [1-(4-(trifluoromethyl)phenyl)-3,4-dihydroquinolin-2(1H)-one], C16H12F3NO
  15. Crystal structure of (E)-2-amino-N′-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)benzohydrazide – dimethylformamide – water (1/1/2), C15H16N4O3·C3H7NO·2H2O
  16. Crystal structure of 3-(4-bromophenyl)-5-methyl-1H-pyrazole, C10H9BrN2
  17. Crystal structure of 1,10-phenanthrolinium bromide dihydrate, C12H9N2Br
  18. Crystal structure of N-(4′-chloro-[1,1′-biphenyl]-2-yl)formamide, C13H10ClNO
  19. The crystal structure of nitroterephthalic acid, C8H5NO6
  20. Crystal structure of (2-((4-bromo-2,6-dichlorophenyl)amino)phenyl) (morpholino)methanone, C17H15BrCl2N2O2
  21. Crystal structure of tetraaqua-bis(ethanol-κO)-tetrakis(μ2-trifluoroacetate-κ2O:O′)-bis(trifluoroacetate-κ2O)digadolinium(III) Gd2C16H20O18F18
  22. The crystal structure of dimethyl 4,4′-[10,20-bis(2,6-difluorophenyl)porphyrin-5,15-diyl]dibenzoate chloroform solvate, C50H32Cl6F4N4O4
  23. The crystal structure of N,N′-((nitroazanediyl)bis(methylene))diacetamide, C6H12O4N4
  24. The crystal structure of [bis(2,2′-bipyridine-6-carboxylato-κ3N,N,O)magnesium(II)]dihydrate, C22H18N4O6Mg
  25. Crystal structure of poly[diaqua-(bis(μ2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′] cobalt(II)-tetraqua-bis(1,4-bis(imidazol-1-ylmethyl)benzene)-κ1N)-cobalt(II) di(2,5-thiophenedicarboxylate) dihydrate, C68H76Co2N16O16S2
  26. Crystal structure of poly[chlorido-μ2-chlorido-(μ2-1-[(2-ethyl-4-methyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κN:N’)cadmium(II)], C13H15CdN5Cl2
  27. The crystal structure of (4-hydroxybenzenesulfonate)-k1O-6,6′-((1E,1′E)- (ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene)) bis(2-methoxyphenol)-κ2N,N,μ2O,O,κ2O, O)-(methanol)-cobalt(II) sodium(I), C25H27CoN2NaO9S
  28. Crystal structure of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)(4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)methanone, C17H18F6N6O
  29. Crystal structure of bis{[(cyclohexylimino)(phenylimino)-l5-(methyl)diethylazane-κ2N:N′]-(ethyl)-zinc(II)]}, C38H62N6Zn2
  30. Crystal structure of 2-[(4-bromobenzyl)thio]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C13H8Br2N2OS2
  31. Crystal structure of 10-methoxy-7,11b,12,13-tetrahydro-6H-pyrazino [2′,3′:5,6]pyrazino[2,1-a]isoquinoline, C15H16N4O
  32. The crystal structure of 1-propyl-2-nitro-imidazole oxide, C6H9N3O3
  33. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid–2-ethoxybenzamide (1/1), C17H16N2O8
  34. The structure of RUB-1, (C8H16N)6[B6Si48O108], a boron containing levyne-type zeolite, occluding N-methyl-quinuclidinium in the cage-like pores
  35. The crystal structure of diaqua-(naphthalene-4,5-dicarboxylate-1,8-dicarboxylic anhydride-κ1O)-(4′-(4-(1H-benzimidazolyl-1-yl)phenyl)-2,2′:6′,2″-terpyridine-κ3N,N′,N″)–manganese(II) dihydrate, C42H27MnN5O9·2H2O
  36. Crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene))bis (3-(3-bromopropoxy)phenol), C20H22Br2N2O4
  37. The crystal structure of 3-(2-hydroxyphenyl)-4-phenyl-6-(p-tolyl)-2H-pyran-2-one, C24H18O3
  38. Crystal structure of bis(μ2-2-(1,5-dimethyl–3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)-(nitrato-κ2O,O′)dicobalt(II), C36H32Co2N8O4
  39. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α] phenanthren-3-one O-(4-fluorobenzoyl) oxime, C28H36FNO2
  40. The crystal structure of 4-aminiumbiphenyl benzenesulfonate, C18H17NO3S
  41. Synthesis and crystal structure of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate, C18H17N3O9
  42. Crystal structure of N-(Ar)-N′-(Ar′)-formamidine, C14H12Br2N2O
  43. The crystal structure of 4-(2,4-dichlorophenyl)-2-(4-fluorophenyl)-5-methyl-1H-imidazole, C16H11Cl2FN2
  44. Crystal structure of 1-(4–chlorophenyl)-4-benzoyl-3-methyl-1H-pyrazol-5-ol, C17H13ClN2O2
  45. The crystal structure of 5-amino-1-methyl-4-nitroimidazole, C4H6O2N4
  46. Crystal structure of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene-N,N′-bis(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-1,3,2-diazaborol-2-yl)-l2-germenediamine, C63H94B2GeN8
  47. The crystal structure of (bromido, chlorido)-tricarbonyl-(5,5′-dimethyl-2,2′-bipyridine)-rhenium(I), C15H12Br0.2Cl0.8N2O3Re1
  48. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
  49. The crystal structure of poly[2-(4-carboxypyridin-3-yl)terephthalpoly[diaqua-(μ4-2-(6-carboxylatopyridin-3-yl)terephthalato-κ5O,N:O′:O″,O‴)]) cadmium(II)] dihydrate, C28H20Cd3N2O16
  50. Crystal structure of [tetraaqua-bis((3-carboxy-5-(pyridin-4-yl)benzoate-κ1N)cobalt(II)] tetrahydrate, C26H32CoN2O16
  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
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 12.10.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2023-0265/html?lang=en
Scroll to top button