Home Crystal structure of 4-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]pyridine, C14H19N3
Article Open Access

Crystal structure of 4-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]pyridine, C14H19N3

  • Harukaze Kanazawa ORCID logo , Edward R. T. Tiekink ORCID logo EMAIL logo and Kiyoshi Fujisawa ORCID logo EMAIL logo
Published/Copyright: March 12, 2025
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 240 Issue 3

Abstract

C14H19N3, monoclinic, P21/c (no. 14), a = 5.64918(12) Å, b = 17.0755(4) Å, c = 13.4012(3) Å, β = 92.053(2)°, V = 1291.88(5) Å3, Z = 4, Rgt(F) = 0.0377, wRref (F2) = 0.0983, T = 178 K.

CCDC no.: 2424009

1 Source of material

The title compound, (I), was prepared in a two-step process. L1(Py)pzTs [3,5-bis(propan-2-yl)-1-(p-toluenesulfonyl)-pyrazol-4-(4′-pyridine)]: A mixture of 2-pyridyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.00 g, 4.88 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.200 g, 0.173 mmol) was stirred in 1,2-dimethoxyethane (DME) (20 mL) at room temperature under an argon atmosphere. To this mixture was added L1(Br)pzTs 5 (1.58 g, 4.10 mmol) in DME (10 mL) and a saturated aqueous Na2CO3 solution (10 mL). The solution was heated to reflux at 393 K overnight under an argon atmosphere and then cooled to ambient temperature. The solution was removed under vacuum, acetone (30 mL) was added followed by filtration to remove undissolved material. The solvent was removed under vacuum. The crude solid was purified via column chromatography on silica gel with acetone and hexane (1/1 v/v) as the eluent to give a cream solid, characterised as L1(Py)pzTs (1.34 g, 3.49 mmol, 85 %). 1H NMR (CDCl3, 500 MHz): δ 1.05 (d, J = 7 Hz, 6H, CHMe2), 1.07 (d, J = 7 Hz, 6H, CHMe2), 2.44 (s, 3H, C6H4 Me), 2.62 (m, J = 7 Hz, 1H, CHMe2), 3.81 (m, J = 7 Hz, 1H, CHMe2), 7.12 (d, J = 6 Hz, 2H, 2,6-py), 7.13 (d, J = 8 Hz, 2H, 3,5–Ts), 7.90 (d, J = 8 Hz, 2H, 2,5–Ts), 8.61 (d, J = 6 Hz, 2H, 3,5-py), NH not observed. The molecular structure is shown in the figure. Table 1 contains crystallographic data.

Table 1:

Data collection and handling.

Crystal: Colourless slab
Size: 0.19 × 0.13 × 0.05 mm
Wavelength:

μ:		 Mo Kα radiation (0.71073 Å)

0.07 mm−1
Diffractometer, scan mode:

θmax, completeness:		 Rigaku XtaLAB P200, φ and ω scan

26.4°, 100 %
N(hkl)measured, N(hkl)unique, Rint: 19063, 2630, 0.025
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2355
N(param)refined: 161
Programs: CrysAlisPRO 1 , IL MILIONE 2 , SHELX 3 , WinGx 4

L1(Py)pzH [3,5-bis(propan-2-yl)-1H-pyrazol-4-(4′-pyridine)]: L1(Py)pzTs (1.34 g, 3.49 mmol) in MeOH (20 mL) was deprotected by heating for 5 h in the presence of 5 M NaOH solution (10 mL). The mixture was subsequently extracted with dichloromethane (3 × 15 mL). The organic layers were combined and washed with aqueous saturated NaCl solution and dried over MgSO4. The solvent was removed under vacuum. The crude solid was purified via column chromatography on silica gel with acetone and hexane (1/1 v/v) as the eluent to give a white solid, L1(Py)pzH (0.59 g, 2.57 mmol, 74 %). Anal. Calcd. for C14H19N3: C 73.33, H 8.35, N 18.32; Found: C 73.21, H 8.52, N 18.41 %. IR (KBr, cm−1): 3147s ν(N–H), 3110 s ν(N–H), 3061 s ν(C–H aromatic ), 3004 s ν(C–H aromatic ), 2968 s ν(C–H aliphatic ), 2929 m ν(C–H aliphatic ), 2870 m ν(C–H aliphatic ), 1601 s ν(C=N), 1568 m ν(C=N). 1H NMR (CDCl3, 500 MHz): δ 1.22 (d, J = 7 Hz, 12H, CHMe2), 3.04 (m, J = 7 Hz, 2H, CHMe2), 7.19 (d, J = 6 Hz, 2H, 2,6-py), 8.62 (d, J = 6 Hz, 2H, 3,5-py), NH not observed. 13C NMR (CDCl3, 125 MHz): δ 22.5 (CHMe2), 25.4 (CHMe2), 113.8 (4-pz), 124.9 (2,6-py), 142.8 (1-py), 149.9 (3,5-py), 3,5-pz not observed.

2 Experimental details

The C-bound H atoms were geometrically placed (C–H = 0.95–1.00 Å) and refined as riding with Uiso (H) = 1.2–1.5Ueq (C). The N-bound H atom was refined with N–H = 0.88 + -0.01 Å and with Uiso (H) = 1.2Ueq (N).

3 Discussion

Coinage metal(I)-based, cyclic trinuclear complexes have been extensively studied as they represent a fascinating class of trinuclear metallocycles with M(I)⋯M(I) interactions. 6 One of the useful ligands used to generate these complexes is pyrazole, a five-numbered, heterocyclic aromatic ring. The present study was motivated by continuing interest in the exploration of the effects of the pyrazole substituent(s) upon the structures and physicochemical properties of these trinuclear complexes. In this connection, recently, halide and phenyl groups were successfully introduced into the 4-position of the pyrazole ring. 5 , 7 In this contribution, a pyridyl group has been introduced into the 4-position of the pyrazole ring employing a similar synthetic method used for the introduction of a phenyl group into the 4-position. 5 Thus, the Suzuki–Miyaura cross-coupling reaction from L1(Br)pzTs 5 was performed to yield L1(Py)pzTs in 85 % yield. After deprotection of L1(Py)pzTs with base, L1(Py)pzH, (I), was obtained in 74 % yield. Related synthetic methods to generate 3,5-dimethyl-4-(4′-pyridyl)pyrazole 8 and 3,5-diethyl-4-(4′-pyridyl)pyrazole 9 have been published.

The IR spectrum of L1(Py)pzH, (I), features a complicated pattern of absorption bands between 3147 and 3110 cm−1, assigned to N–H stretching, which is clearly different from the single, strong absorption band at 3219 cm−1 of L1(Ph)pzH. 5 This complicated pattern is likely to arise from the hydrogen-bonding in the crystal (see below). Moreover, a strong absorption band at 1601 cm−1, absent in the IR spectrum of L1(Ph)pzH, 5 was observed for (I), assignable to ν(C=N) of the pyridyl substituent. The expected signal in 1H NMR spectrum of L1(Py)pzH due to methyl–H appeared at 1.22 ppm, which is shifted downfield compared to those of the precursor, L1(Py)pzTs, which resonated at 1.05 and 1.07 ppm. 5 Further, solid-state details of (I) were revealed through an X-ray crystallographic study. The molecular structure is shown in the figure. Table 1 contains the crystallographic data. The list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

The molecular structure of (I) is illustrated in the upper view of the figure (70 % displacement ellipsoids). The molecule comprises a 1,2-pyrazolyl ring substituted in the 4-position by a pyridyl group, and in the 3- and 5-positions by i-propyl groups. The wider angle subtended at the N1 atom cf. the N2 atom, i.e. 113.24(9) and 105.03(9)°, respectively, confirms protonation at the N1 atom. Within the pyrazolyl ring, there are significant disparities in the C–N bond lengths, i.e. C4–N1 = 1.3516(14) Å and C6–N2 = 1.3291(14) Å, and between the C–C bonds, i.e. C4–C5 = 1.3887(16) Å and C5–C6 = 1.4238(15) Å, consistent with significant localisation of π-electron density in the C6–N2 and C4–C5 bonds. The angle between the least-squares planes through the five- and six-membered rings is 40.83(6)°, indicating a twisted confirmation. The N1–N2 bond length is 1.3557(14) Å.

The title bifunctional ligand, containing both pyridyl and pyrazolyl residues, (I), is the i-propyl derivative of the previously explored methyl, (II), and ethyl, (III), species. Of these, only (II) has been characterised crystallographically, as a hydrate. 10 In (II), 10 with two independent molecules in the asymmetric-unit, the dihedral angles between the five- and six-membered rings are 36.48(10) and 47.25(9)°, i.e. a range of angles incorporating the value in (I). Similar trends in C–N bond lengths were noted in (II) and in the C–C bond lengths for one of the independent molecules of (II) but not in the second independent molecule; rather high standard uncertainty values in (II) are noted.

These bifunctional molecules have been noted for their ability to form a mononuclear species with (II), i.e. pyridyl-bound in all-trans Ph2SnCl2(II)2, 8 and a two-dimensional coordination polymer with bridging, via pyrazolyl- and pyridyl–N atoms derived from two molecules of (III), i.e. in six-coordinate {CdCl2(III)2} n . 11

In the molecular packing of (I), pyrazolyl–N–H⋯N(pyridyl) hydrogen bonds [N1–H1n⋯N3 i : H1n⋯N3 i  = 2.034(12) Å, N1⋯N3 i  = 2.8794(14) Å with angle at H1n = 157.6(11)° for symmetry operation (i): 1 + x, 1/2 −y, −1/2 + z] within supramolecular chains are apparent as shown in the lower view of the figure. These have a twisted topology and are aligned along [2 0 −1]. The chains assemble into a layer parallel to (1 0 1) featuring several C–H⋯π(pyrazolyl, pyridyl) interactions between them. The shortest and most directional of these is a pyridyl–C–H⋯π(pyrazolyl) contact [C12–H12⋯Cg(pyrazolyl) ii : H12⋯Cg(pyrazolyl) ii  = 2.55 Å, C12⋯Cg(pyrazolyl) ii  = 3.3744(12) Å with angle at H12 = 145° for (ii): −1 + x, y, z]. The shortest contact between layers along the b-axis are of the type H⋯H [C2–H2a⋯H2a iii : H2a⋯H2a iii  = 2.31 Å, C2⋯H2a iii  = 3.09 Å with angle at H2a = 135° for (iii): −x, 1 −y, 1 −z]. A comparison between the molecular packing in (I) and that of (II) 10 is not valid owing the presence of water molecules of crystallisation in the latter.

The dominance of hydrogen in forming surface contacts between layers in the molecular packing was confirmed by an analysis of the calculated Hirshfeld surface and two-dimensional fingerprint plots using CrystalExplorer 12 and following standard protocols. 13 The H⋯H surface contacts amounted to 66.5 %, following by 17.4 % for N⋯H/H⋯N and 15.6 % for C⋯H/H⋯C contacts; the remaining 0.5 % was accounted for by C⋯C contacts.

Corresponding authors: Edward R. T. Tiekink, Department of Chemistry, Universitat de les Illes Balears, Crta de Valldemossa km 7.5, 07122 Palma de Mallorca, Spain, E-mail: ; and Kiyoshi Fujisawa, Department of Chemistry, Ibaraki University, Mito, Ibaraki 310–8512, Japan, E-mail:

Acknowledgments

This research was supported by the Joint Usage/Research Centre for Catalysis and the Koyanagi Foundation.

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

  2. Research funding: This study was financially supported by the Joint Usage/Research Centre for Catalysis (Proposals 22DS0143, 23DS0198 and 24ES0584).

  3. Conflict of interest: The authors declare no conflicts of interest.

References

1. Rigaku Oxford Diffraction. CrysAlisPRO; Rigaku Corporation: Oxford, UK, 2021.Search in Google Scholar

2. Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Siliqi, D.; Spagna, R. IL MILIONE: a Suite of Computer Programs for Crystal Structure Solution of Proteins. J. Appl. Cryst. 2007, 40, 609–613; https://doi.org/10.1107/S0021889807010941.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 PubMed PubMed Central

4. Farrugia, L. J. WinGX and ORTEP for Windows: an Update. J. Appl. Cryst. 2012, 45, 849–854; https://doi.org/10.1107/S0021889812029111.Search in Google Scholar

5. Saotome, M.; Shimizu, D.; Itagaki, A.; Young, D. J.; Fujisawa, K. Structures and Photoluminescence of Silver(I) and Gold(I) Cyclic Trinuclear Complexes with Aryl Substituted Pyrazolates. Chem. Lett. 2019, 48, 533–536; https://doi.org/10.1246/cl.190145.Search in Google Scholar

6. Zheng, J.; Lu, Z.; Wu, K.; Ning, G.-H.; Li, D. Coinage-metal-based Cyclic Trinuclear Complexes with Metal-Metal Interactions: Theories to Experiments and Structures to Functions. Chem. Rev. 2020, 120, 9675–9742; https://doi.org/10.1021/acs.chemrev.0c00011.Search in Google Scholar PubMed

7. Morishima, Y.; Young, D. J.; Fujisawa, K. Structure and Photoluminescence of Silver(I) Trinuclear Halopyrazolato Complexes. Dalton Trans. 2014, 43, 15915–15928; https://doi.org/10.1039/C4DT01978D.Search in Google Scholar PubMed

8. Cui, Q.; Cao, X.-Y.; Tang, L.-F. Diorganotin(IV) Derivatives Containing the 3,5-Dimethyl-4-(4′-pyridyl)pyrazole Ligand. Polyhedron 2005, 24, 209–214; https://doi.org/10.1016/j.poly.2004.11.016.Search in Google Scholar

9. Hou, L.; Shi, W.-J.; Wang, Y.-Y.; Wang, H.-H.; Cui, L.; Chen, P.-X.; Shi, Q.-Z. Trinuclear-based Copper(I) Pyrazolate Polymers: Effect of Trimer π-acid⃛halide/pseudohalide Interactions on the Supramolecular Structure and Phosphorescence. Inorg. Chem. 2011, 50, 261–270; https://doi.org/10.1021/ic101901w.Search in Google Scholar PubMed

10. Li, H.; Jin, Q.-H.; Yu, S.-Y.; Ma, H.-W.; Li, Y. Crystal Structure of 4-(4-pyridil)-3,5-dimethylpyrozole Hydrate, (C5H4N)CH3(C3N2H)CH3·H2O. Z. Kristallogr. New Cryst. Struct. 2004, 219, 13–14; https://doi.org/10.1524/ncrs.2004.219.1.13.Search in Google Scholar

11. Shi, W.-J.; Jiang, C.-Y.; Ma, L.-N.; Wang, X.-Q.; Hou, L. Two New Coordination Polymers Based on a Pyridine-Pyrazole Bifunctional Linker: Synthesis, Structure and Luminescent Properties. Inorg. Chem. Commun. 2018, 96, 128–132; https://doi.org/10.1016/j.inoche.2018.08.014.Search in Google Scholar

12. Spackman, P. R.; Turner, M. J.; McKinnon, J. J.; Wolff, S. K.; Grimwood, D. J.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer: A Program for Hirshfeld Surface Analysis, Visualization and Quantitative Analysis of Molecular Crystals. J. Appl. Crystallogr. 2021, 54, 1006–1011; https://doi.org/10.1107/S1600576721002910.Search in Google Scholar PubMed PubMed Central

13. Tan, S. L.; Jotani, M. M.; Tiekink, E. R. T. Utilizing Hirshfeld Surface Calculations, Non-covalent Interaction (NCI) Plots and the Calculation of Interaction Energies in the Analysis of Molecular Packing. Acta Crystallogr. 2019, E75, 308–318; https://doi.org/10.1107/S2056989019001129.Search in Google Scholar PubMed PubMed Central

Received: 2025-01-25
Accepted: 2025-02-14
Published Online: 2025-03-12
Published in Print: 2025-06-26

© 2025 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. Crystal structure of 5,5′-bis(2,4,6-trinitrophenyl)-2,2′-bi(1,3,4-oxadiazole), C16H4N10O14
  4. Crystal structure of catena-poly[(μ3-4,4′-oxydibenzoato- κ5 O,O′: O″,O‴:O‴)-bis(2,4,6-tri(3-pyridine)-1,3,5-triazine-κ1 N)cadmium(II)], C50H32CdN12O5
  5. The crystal structure of 1,4-diazepane-1,4-diium potassium trinitrate, C5H14KN5O9
  6. The crystal structure of benzyl 2,2,5,5-tetramethylthiazolidine-4-carboxylate, C15H21NO2S
  7. Crystal structure of 2-hydroxyethyl-triphenylphosphonium tetracyanidoborate, C24H20BN4OP
  8. The crystal structure of 1-methyl-3-(N-methylnitrous amide–N-methylene) imidazolidine-2,4,5-trione
  9. Crystal structure of N-((3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(2,2,2-trifluoroacetyl)-1H-pyrazol-5-yl)carbamoyl)-2,6-difluorobenzamide, C20H7Cl2F8N5O3S
  10. Crystal structure of 5-(2,2-difluoropropyl)-5-methylbenzo[4,5]imidazo[2,1-a] isoquinolin-6(5H)-one, C20H18F2N2O
  11. The crystal structure of N′,N″-[1,2-bis(4-chlorophenyl)ethane-1,2-diylidene]bis(furan-2- carbohydrazide), C24H16Cl2N4O4
  12. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromoantimony(III), [C25H21BrP]+[SbBr4]−
  13. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromidoindium(III), [C25H21BrP]+[InBr4]−
  14. The crystal structure of 4-carboxy-2-oxobutan-1-aminium chloride, C5H10ClNO3
  15. Crystal structure of (4-(4-chlorophenyl)-1H-pyrrole-3-carbonyl)ferrocene, C21H16ClFeNO
  16. The crystal structure of dichlorido(η6-p-cymene)(triphenylarsine)ruthenium(II), C28H29AsCl2Ru
  17. Crystal structure of (Z)-2-hydroxy-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H16N2O2
  18. The crystal structure of 10-(1-bromoethyl)-14-(bromomethyl)dibenzo[a, c]acridine, C24H17NBr2
  19. Synthesis and crystal structure of 6-methoxy-7-[(4-methoxyphenyl)methoxy]-2H-1-benzopyran-2-one, C18H16O5
  20. Synthesis and crystal structure of ethyl 4-((4-trifluoromethylbenzyl)amino)benzo, C17H16F3NO2
  21. The crystal structure of (Z)-2-(tert-butyl)-6-(7-(tert-butyl)-5-methylbenzo[d][1,3]oxathiol-2-ylidene)-4-methylcyclohexa-2,4-dien-1-one, C23H28O2S
  22. The crystal structure of (R)-2-aminobutanamide hydrochloride, C4H11ClN2O
  23. Crystal structure of bromido[hydridotris(3-tert-butyl-5-isopropylpyrazolyl)borato-κ3 N,N′,N″]copper(II), C30H52BBrCuN6
  24. Crystal structure of chlorido{hydridotris[3-mesityl-5-methyl-1H-pyrazol-1-yl-κN3]borato}-copper(II) dichloromethane monosolvate
  25. Crystal structure of 4-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]pyridine, C14H19N3
  26. Crystal structure of ((4-(4-bromophenyl)-1H-pyrrol-3-yl)methyl)ferrocene, C21H16BrFeNO
  27. Crystal structure of [(4-chlorobenzyl)triphenylphosphonium] dichloridocopper(I), {[C25H21ClP]+[CuCl2]−}n
  28. The crystal structure of {Cu(2,9-diisopropyl-4,7-diphenyl-1,10-phenanthroline)[4,5-bis(diphenylphosphino)-9,9-dimethylxanthene]}+ PF6−·1.5(EtOAC)
  29. Crystal structure of 3,5-bis(t-butyl)-1H-pyrazol-4-amine, C11H21N3
  30. Crystal structure of [(2,4-dichlorobenzyl)triphenylphosphonium] trichloridocopper(II), [C25H20Cl2P]+[CuCl3]−
  31. The crystal structure of dipotassium sulfide, K2S
  32. Crystal structure of (4-(4-methoxyphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C22H19FeNO2
  33. Crystal structure of (E)-6-(4-methylpiperazin-1-yl)-2-(4-(trifluoromethyl)benzylidene)-3, 4-dihydronaphthalen-1(2H)-one, C23H23F3N2O
  34. Crystal structure of (E)-6-morpholino-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H20F3NO2
  35. Crystal structure of Ce9Ir37Ge25
  36. The crystal structure of ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate, C14H11N3O4S
  37. Crystal structure of (4-(4-isopropylphenyl)-1H-pyrrol-3-yl)(ferrocenyl)methanone, C24H23FeNO
  38. Crystal structure of bis(methylammonium) tetrathiotungstate(VI), (CH3NH3)2[WS4]
  39. Crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one, C17H12O2
  40. Crystal structure of 3-[(4-phenylpiperidin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4- oxadiazole-2-thione, C18H19N3OS2
  41. Crystal structure of N-isopropyl-1,8-naphthalimide C15H13NO2
  42. TiNiSi-type EuPdBi
  43. Crystal structure of 1-(p-tolylphenyl)-4-(2-thienoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O2S
  44. The crystal structure of 3-(3-carboxypropyl)-2-nitro-1H-pyrrole 1-oxide, C7H9N3O5
  45. The crystal structure of tetraaqua-bis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k2O:N)-tetrakis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k1N)trizinc(II) hexahydrate C36H52N18O32Zn3
  46. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-hydroxy-3,5-dimethoxybenzoate monohydrate, C25H30FN3O9
  47. Crystal structure of bis(DL-1-carboxy-2-(1H-indol-3-yl)ethan-1-aminium) oxalate — acetic acid (1/2)
  48. Crystal structure of methyl (E)-4-((4-methylphenyl)sulfonamido)but-2-enoate, C12H15NO4S
  49. The crystal structure of actarit, C10H11NO3
  50. The crystal structure of bicyclol, C19H18O9
  51. The crystal structure of topiroxostat, C13H8N6
  52. Crystal structure of 2,2-dichloro-N-methyl-N-(4-p-tolylthiazol-2-yl)acetamide, C13H12Cl2N2OS
  53. Crystal structure of 4-(trifluoromethyl)-7-coumarinyl trifluoromethanesulfonate C11H4F6O5S
  54. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6)-((Z)-N,N′-bis(2-(dimethylamino)phenyl)carbamimidato-κ1N)potassium(I)
  55. Crystal structure of (Z)-2-(5-((4-(dimethylamino)naphthalen-1-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid, C18H16N2O3S2
  56. Crystal structure of (4-fluorobenzyl)triphenylphosphonium bromide, C25H21BrFP
  57. The crystal structure of dichlorido-[6-(pyridin-2-yl)phenanthridine-κ2N, N′]zinc(II)-chloroform (1/1), C19H13N2ZnCl5
  58. Crystal structure of (E)-(3-(2,4-dichlorophenyl)acryloyl)ferrocene, C19H14Cl2FeO
  59. The crystal structure of (E)-7-chloro-1-cyclopropyl-6-fluoro-3-((2-hydroxybenzylidene)amino)quinolin-4(1H)-one, C19H14ClFN2O2
  60. Crystal structure of 2-bromo-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13BrFNO4S2
  61. Crystal structure of 2-chloro-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13ClFNO4S2
  62. Crystal structure of 5-(2,2-difluoropropyl)-5-methyl-6-oxo-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline-3-carbonitrile, C20H15F2N3O
https://doi.org/10.1515/ncrs-2025-0048
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of 5,5′-bis(2,4,6-trinitrophenyl)-2,2′-bi(1,3,4-oxadiazole), C16H4N10O14
  4. Crystal structure of catena-poly[(μ3-4,4′-oxydibenzoato- κ5 O,O′: O″,O‴:O‴)-bis(2,4,6-tri(3-pyridine)-1,3,5-triazine-κ1 N)cadmium(II)], C50H32CdN12O5
  5. The crystal structure of 1,4-diazepane-1,4-diium potassium trinitrate, C5H14KN5O9
  6. The crystal structure of benzyl 2,2,5,5-tetramethylthiazolidine-4-carboxylate, C15H21NO2S
  7. Crystal structure of 2-hydroxyethyl-triphenylphosphonium tetracyanidoborate, C24H20BN4OP
  8. The crystal structure of 1-methyl-3-(N-methylnitrous amide–N-methylene) imidazolidine-2,4,5-trione
  9. Crystal structure of N-((3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(2,2,2-trifluoroacetyl)-1H-pyrazol-5-yl)carbamoyl)-2,6-difluorobenzamide, C20H7Cl2F8N5O3S
  10. Crystal structure of 5-(2,2-difluoropropyl)-5-methylbenzo[4,5]imidazo[2,1-a] isoquinolin-6(5H)-one, C20H18F2N2O
  11. The crystal structure of N′,N″-[1,2-bis(4-chlorophenyl)ethane-1,2-diylidene]bis(furan-2- carbohydrazide), C24H16Cl2N4O4
  12. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromoantimony(III), [C25H21BrP]+[SbBr4]−
  13. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromidoindium(III), [C25H21BrP]+[InBr4]−
  14. The crystal structure of 4-carboxy-2-oxobutan-1-aminium chloride, C5H10ClNO3
  15. Crystal structure of (4-(4-chlorophenyl)-1H-pyrrole-3-carbonyl)ferrocene, C21H16ClFeNO
  16. The crystal structure of dichlorido(η6-p-cymene)(triphenylarsine)ruthenium(II), C28H29AsCl2Ru
  17. Crystal structure of (Z)-2-hydroxy-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H16N2O2
  18. The crystal structure of 10-(1-bromoethyl)-14-(bromomethyl)dibenzo[a, c]acridine, C24H17NBr2
  19. Synthesis and crystal structure of 6-methoxy-7-[(4-methoxyphenyl)methoxy]-2H-1-benzopyran-2-one, C18H16O5
  20. Synthesis and crystal structure of ethyl 4-((4-trifluoromethylbenzyl)amino)benzo, C17H16F3NO2
  21. The crystal structure of (Z)-2-(tert-butyl)-6-(7-(tert-butyl)-5-methylbenzo[d][1,3]oxathiol-2-ylidene)-4-methylcyclohexa-2,4-dien-1-one, C23H28O2S
  22. The crystal structure of (R)-2-aminobutanamide hydrochloride, C4H11ClN2O
  23. Crystal structure of bromido[hydridotris(3-tert-butyl-5-isopropylpyrazolyl)borato-κ3 N,N′,N″]copper(II), C30H52BBrCuN6
  24. Crystal structure of chlorido{hydridotris[3-mesityl-5-methyl-1H-pyrazol-1-yl-κN3]borato}-copper(II) dichloromethane monosolvate
  25. Crystal structure of 4-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]pyridine, C14H19N3
  26. Crystal structure of ((4-(4-bromophenyl)-1H-pyrrol-3-yl)methyl)ferrocene, C21H16BrFeNO
  27. Crystal structure of [(4-chlorobenzyl)triphenylphosphonium] dichloridocopper(I), {[C25H21ClP]+[CuCl2]−}n
  28. The crystal structure of {Cu(2,9-diisopropyl-4,7-diphenyl-1,10-phenanthroline)[4,5-bis(diphenylphosphino)-9,9-dimethylxanthene]}+ PF6−·1.5(EtOAC)
  29. Crystal structure of 3,5-bis(t-butyl)-1H-pyrazol-4-amine, C11H21N3
  30. Crystal structure of [(2,4-dichlorobenzyl)triphenylphosphonium] trichloridocopper(II), [C25H20Cl2P]+[CuCl3]−
  31. The crystal structure of dipotassium sulfide, K2S
  32. Crystal structure of (4-(4-methoxyphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C22H19FeNO2
  33. Crystal structure of (E)-6-(4-methylpiperazin-1-yl)-2-(4-(trifluoromethyl)benzylidene)-3, 4-dihydronaphthalen-1(2H)-one, C23H23F3N2O
  34. Crystal structure of (E)-6-morpholino-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H20F3NO2
  35. Crystal structure of Ce9Ir37Ge25
  36. The crystal structure of ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate, C14H11N3O4S
  37. Crystal structure of (4-(4-isopropylphenyl)-1H-pyrrol-3-yl)(ferrocenyl)methanone, C24H23FeNO
  38. Crystal structure of bis(methylammonium) tetrathiotungstate(VI), (CH3NH3)2[WS4]
  39. Crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one, C17H12O2
  40. Crystal structure of 3-[(4-phenylpiperidin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4- oxadiazole-2-thione, C18H19N3OS2
  41. Crystal structure of N-isopropyl-1,8-naphthalimide C15H13NO2
  42. TiNiSi-type EuPdBi
  43. Crystal structure of 1-(p-tolylphenyl)-4-(2-thienoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O2S
  44. The crystal structure of 3-(3-carboxypropyl)-2-nitro-1H-pyrrole 1-oxide, C7H9N3O5
  45. The crystal structure of tetraaqua-bis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k2O:N)-tetrakis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k1N)trizinc(II) hexahydrate C36H52N18O32Zn3
  46. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-hydroxy-3,5-dimethoxybenzoate monohydrate, C25H30FN3O9
  47. Crystal structure of bis(DL-1-carboxy-2-(1H-indol-3-yl)ethan-1-aminium) oxalate — acetic acid (1/2)
  48. Crystal structure of methyl (E)-4-((4-methylphenyl)sulfonamido)but-2-enoate, C12H15NO4S
  49. The crystal structure of actarit, C10H11NO3
  50. The crystal structure of bicyclol, C19H18O9
  51. The crystal structure of topiroxostat, C13H8N6
  52. Crystal structure of 2,2-dichloro-N-methyl-N-(4-p-tolylthiazol-2-yl)acetamide, C13H12Cl2N2OS
  53. Crystal structure of 4-(trifluoromethyl)-7-coumarinyl trifluoromethanesulfonate C11H4F6O5S
  54. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6)-((Z)-N,N′-bis(2-(dimethylamino)phenyl)carbamimidato-κ1N)potassium(I)
  55. Crystal structure of (Z)-2-(5-((4-(dimethylamino)naphthalen-1-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid, C18H16N2O3S2
  56. Crystal structure of (4-fluorobenzyl)triphenylphosphonium bromide, C25H21BrFP
  57. The crystal structure of dichlorido-[6-(pyridin-2-yl)phenanthridine-κ2N, N′]zinc(II)-chloroform (1/1), C19H13N2ZnCl5
  58. Crystal structure of (E)-(3-(2,4-dichlorophenyl)acryloyl)ferrocene, C19H14Cl2FeO
  59. The crystal structure of (E)-7-chloro-1-cyclopropyl-6-fluoro-3-((2-hydroxybenzylidene)amino)quinolin-4(1H)-one, C19H14ClFN2O2
  60. Crystal structure of 2-bromo-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13BrFNO4S2
  61. Crystal structure of 2-chloro-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13ClFNO4S2
  62. Crystal structure of 5-(2,2-difluoropropyl)-5-methyl-6-oxo-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline-3-carbonitrile, C20H15F2N3O
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 9.10.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2025-0048/html?srsltid=AfmBOooQ9M-oseQuOEhaQMwMgM5NeSohaHMPT9tHOXGPLz66uxrFRIEv
Scroll to top button