Startseite The crystal structure of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2
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The crystal structure of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2

  • Limin Zuo ORCID logo , Xia Zhou , Yitong Liu , Yongsheng Gu , Yifei Jiang , Xiaofang Lian , Huiyi Liu , Qingying Jia und Guangzhi Shan EMAIL logo
Veröffentlicht/Copyright: 13. Januar 2025
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 240 Heft 2

Abstract

C18H17BrFN5O2, monoclinic, P21/c (no. 14), a = 19.3571(8) Å, b = 13.4295(12) Å, c = 7.3036(5) Å, β = 93.372(5)°, V = 1895.3(2) Å3, Z = 4, Rgt(F) = 0.0407, wRref(F2) = 0.0939, T = 293(2) K.

CCDC no.: 2329150

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: 0.06 × 0.04 × 0.04 mm
Wavelength:

μ:		 Mo Kα radiation (0.71073 Å)

2.20 mm−1
Diffractometer, scan mode:

θmax, completeness:		 Xcalibur, ω

26.4°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 10297, 3860, 0.026
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2637
N(param)refined: 250
Programs: CrysAlisPRO, 1 SHELX, 2 , 3 Olex2 4
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.72938 (11) 0.43438 (19) 0.7756 (3) 0.0327 (6)
C2 0.79670 (12) 0.4597 (2) 0.8336 (3) 0.0376 (6)
H2A 0.80567 0.519046 0.896298 0.045*
C3 0.85029 (12) 0.3959 (2) 0.7971 (4) 0.0458 (7)
C4 0.83645 (14) 0.3080 (3) 0.7075 (4) 0.0536 (8)
C5 0.77037 (14) 0.2829 (2) 0.6475 (4) 0.0509 (7)
H5A 0.761745 0.22327 0.585604 0.061*
C6 0.71652 (13) 0.3472 (2) 0.6800 (4) 0.0397 (6)
H6 0.671623 0.331573 0.637293 0.048*
C7 0.60637 (11) 0.48965 (18) 0.8020 (3) 0.0303 (5)
C8 0.57539 (11) 0.39972 (18) 0.8752 (3) 0.0305 (5)
C9 0.50339 (11) 0.37113 (19) 0.8577 (3) 0.0318 (5)
C10 0.38035 (11) 0.3831 (2) 0.7630 (4) 0.0380 (6)
H10A 0.366533 0.364216 0.883764 0.046*
H10B 0.378632 0.324158 0.686054 0.046*
C11 0.33097 (12) 0.4613 (2) 0.6813 (4) 0.0402 (6)
H11A 0.350734 0.489838 0.574199 0.048*
H11B 0.326634 0.514246 0.770181 0.048*
C12 0.25925 (12) 0.4216 (2) 0.6260 (3) 0.0380 (6)
C13 0.20065 (13) 0.4734 (2) 0.6698 (4) 0.0497 (7)
H13 0.205343 0.531251 0.739384 0.060*
C14 0.13492 (14) 0.4405 (3) 0.6116 (5) 0.0630 (9)
H14 0.096497 0.476592 0.643901 0.076*
C15 0.05347 (16) 0.3210 (4) 0.4412 (6) 0.0990 (15)
H15A 0.048089 0.327447 0.310233 0.0148*
H15B 0.019271 0.360875 0.496739 0.0148*
H15C 0.047673 0.252481 0.474696 0.0148*
C16 0.12531 (14) 0.3560 (3) 0.5076 (4) 0.0603 (9)
C17 0.18365 (15) 0.3036 (3) 0.4635 (4) 0.0586 (8)
H17 0.178784 0.245772 0.393767 0.070*
C18 0.24932 (13) 0.3362 (2) 0.5220 (4) 0.0495 (7)
H18 0.287658 0.29967 0.49049 0.059*
Br1 0.94188 (2) 0.43025 (3) 0.87206 (6) 0.07940 (17)
F1 0.88868 (9) 0.24441 (17) 0.6762 (3) 0.0908 (7)
O1 0.56326 (9) 0.25914 (14) 0.10092 (3) 0.0515 (5)
O2 0.59640 (9) 0.64009 (13) 0.6824 (3) 0.0476 (5)
H2 0.567884 0.681046 0.642716 0.071*
N1 0.45057 (10) 0.42250 (16) 0.7770 (3) 0.0395 (5)
H1 0.458366 0.480367 0.732229 0.047*
N2 0.49646 (10) 0.28461 (17) 0.9373 (3) 0.0397 (5)
N3 0.60994 (11) 0.33207 (18) 0.9682 (3) 0.0458 (6)
N4 0.56206 (10) 0.55558 (15) 0.7431 (3) 0.0363 (5)
N5 0.67686 (10) 0.50493 (18) 0.8114 (3) 0.0386 (5)
H5 0.6859 (13) 0.5620 (20) 0.7870 (30) 0.030 (7)*

1 Source of material

The title compound was prepared using a multi-step approach via one pot reaction. Firstly, malononitrile (9.90 g, 0.15 mol) was dissolved in dilute hydrochloric acid (151 ml), After undergoing nitrification, rearrangement, and dehydration reactions, then add sodium chloride (10.40 g, 177.8 mmol), 29 ml of 6 N hydrochloric acid, 60 ml of acetic acid, and dropwise addition of sodium nitrite (4.00 g, 58.0 mmol) to obtain intermediates through diazotization reaction. The intermediates then react with 3-bromo-4-fluoroaniline and N, N-carbonyl diimidazole, respectively. The products were washed once with 60 ml of 1 N hydrochloric acid, 60 ml of water and saturated sodium chloride solution, dried with anhydrous sulfuric acid and filtered. The product was oxidized in 30 ml of 30 % hydrogen peroxide solution, 90 ml of trifluoroacetic acid in an oil bath at 45 °C and then reacted with 4-methylphenylethylamine, and the reaction was shown to be completed by thin layer chromatography (TLC) (petroleum ether: acetate = 4:1, v/v), and the final product was deprotected under alkaline conditions. Crystals were obtained by slow evaporating a mixture of dichloromethane and methanol (1:1, v/v) at room temperature.

2 Experimental details

The structure was solved with the olex2.Solve structure solution program using Charge Flipping and refined with the SHELXL refinement package. The Uiso values of the hydrogen atoms of methyl group and hydroxyl group were set to 1.5 Ueq and the Uiso values of all other hydrogen atoms were set to 1.2 Ueq(C).

3 Comment

Indoleamine 2,3-dioxygenase 1 (IDO1) is a heme containing enzyme that catalyzes the cleavage of the tryptophan ring to N-formylkynurenine in the pathway of kynurenine metabolism, and is a key rate limiting enzyme mediating this metabolic pathway. 5 The compounds in this report were designed and synthesized as novel N-hydroxyamidinium derivatives by structural modification of side-chain aminosulfonamides based on the structure of the crystal complex of Epacadostat with IDO1 enzyme in combination with a similar molecular structure that has been previously reported, 6 , 7 using Epacadostat, an IDO1 inhibitor that is in phase III clinical trials, as a lead.

The crystal structure is monoclinic, with an asymmetric unit consisting of one molecule (Figure) which comprises four planar groups, namely: benzene ring (A: C1–C6, Br1, F1), N-hydroxyamidine (B: C7, N4–N5, O2), furazan ring (C: C8–C9, N2–N3, O1) and methylphenethylamine (D: C10–C18, N1). In the crystal structure, the bromine and fluorine atoms are bonded to the benzene ring with C(3)–Br(1), C(4)–F(1) bonds, respectively. The C(3)–Br(1), C(4)–F(1) bond lengths were determined as 1.882(3) Å and 1.353(3) Å. In addition, the bond length of N(2)–O(1) and N(3)–O(1) on furazan ring are 1.409(3) Å and 1.377(3) Å, respectively. The bond lengths and bond angles all fall within the normal range. 8

Corresponding author: Guangzhi Shan, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050, China, E-mail:

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

  2. Research funding: The work was sponsored by the CAMS Initiative Fund for Innovative Medicine (No. 2021-I2M-1-070).

  3. Competing interests: The authors declare no conflicts of interest regarding this article.

References

1. Rigaku Oxford Diffraction: CrysAlisPRO Software system, version 1.171.39.32a; Rigaku Corporation: Oxford, UK, 2017.Suche in Google Scholar

2. Sheldrick, G. M. Shelxtl – Integrated Space-Group and Crystal-Structure Determination. Acta Crystallogr. 2015, A71, 3–8.10.1107/S2053273314026370Suche 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.Suche in Google Scholar

4. 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.Suche in Google Scholar

5. Fang, K.; Dong, G.; Li, Y.; He, S.; Wu, Y.; Wu, S.; Wang, W.; Sheng, C. Discovery of Novel Indoleamine 2,3–Dioxygenase 1 (Ido1) and Histone Deacetylase (HDAC) Dual Inhibitors. ACS Med. Chem. Lett. 2018, 9, 312–317; https://doi.org/10.1021/acsmedchemlett.7b00487.Suche in Google Scholar PubMed PubMed Central

6. Yue, E. W.; Sparks, R.; Polam, P.; Modi, D.; Douty, B.; Wayland, B.; Glass, B.; Takvorian, A.; Glenn, J.; Zhu, W.; Bower, M.; Liu, X.; Leffet, L.; Wang, Q.; Bowman, K. J.; Hansbury, M. J.; Wei, M.; Li, Y.; Wynn, R.; Burn, T. C.; Koblish, H. K.; Fridman, J. S.; Emm, T.; Scherle, P. A.; Metcalf, B.; Combs, A. P. INCB24360 (Epacadostat), a Highly Potent and Selective Indoleamine-2,3-Dioxygenase 1 (Ido1) Inhibitor for Immuno-Oncology. ACS Med. Chem. Lett. 2017, 8, 486–491; https://doi.org/10.1021/acsmedchemlett.6b00391.Suche in Google Scholar PubMed PubMed Central

7. Chen, T.; Zhou, J.; Li, Z.; Huang, W.; Luo, Y.; Zhao, Y. Synthesis and Characterization of Furazan Derivatives and Their Evaluation as Antitumor Agents. Chem. Pap. 2019, 73, 2813–2820; https://doi.org/10.1007/s11696-019-00834-6.Suche in Google Scholar

8. Sun, Q.; Liu, Y.; Li, X.; Lu, M.; Lin, Q. Alkali Metals-Based Energetic Coordination Polymers as Promising Primary Explosives: Crystal Structures, Energetic Properties, and Environmental Impact. Chem. A Eur. J. 2018, 24, 14213–14219; https://doi.org/10.1002/chem.201802494.Suche in Google Scholar PubMed

Received: 2024-09-24
Accepted: 2024-11-04
Published Online: 2025-01-13
Published in Print: 2025-04-28

© 2024 the author(s), 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. The crystal structure of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2
  4. Synthesis and crystal structure of ethyl (2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR,E)-10-(((3,4-dichlorobenzyl)oxy)imino)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate
  5. The crystal structure of pyrazole nitrate
  6. Crystal structure of tetramethyl-bis(μ2-2-(2-hydroxy-3-methoxybenzylidene)-1-(6-(2-(2-hydroxy-3-methoxybenzylidene)hydrazine-1-carbonyl)picolinoyl)hydrazin-1-ido-κ4O,N,O′:O′)ditin(II) ─ ethanol (1/2), C54H62N10O14Sn2
  7. Crystal structure of catena-poly[μ3-iodido-(4-bromopyridine-κ1N)copper(I)], C5H4BrNCuI
  8. The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P
  9. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(phenylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C34H48N2O
  10. The crystal structure of (E)-3-((E)-3-(4-ethoxy-3-methoxyphenyl)-1-hydroxyallylidene) chroman-2,4-dione, C21H18O6
  11. The crystal structure of trans–L/D-[bis-(2-methyl-8-hydroxyquinoline-κ2 N,O) bis-(1,3,5-triaza-7-phosphaadamantane-κ2 P)cobalt(III)] tetrafluoroborate
  12. Crystal structure of 9-chloro-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C14H15ClN4
  13. Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3
  14. The crystal structure of 4–bromo-3,5-dinitropyrazole
  15. Crystal structure of 8-hydroxy-3,5,8a-trimethyl-7,8,8a,9-tetrahydronaphtho[2,3-b]furan-4,6-dione, C15H16O4
  16. Crystal structure of 5-hydroxy-3,5,8a-trimethyl-4a,5,6,7,8a,9-hexahydronaphtho[2,3-b]furan-4,8-dione, C15H18O4
  17. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(p-tolylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C35H50N2O
  18. The crystal structure of catena-poly((μ2-1,3,5-tri(1H- imidazol-1-yl)benzene κ2N:N′)-bis(4-hydroxbenzoato-κ1O)-zinc(II) monohydrate), C29H24N6O7Zn
  19. Crystal structure of 2-(benzo[d]oxazol-2-yl)acetonitrile, C9H6N2O
  20. Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7
  21. The crystal structure of the double salt potassium 1-methylpiperazine-1,4-di-ium trinitrate, C5H14KN5O9
  22. Crystal structure of 5′-hydroxy-6′-methoxy-1′-methyl-2′,3′,8′,8a′-tetrahydro-1′H-spiro[cyclohexane-1,7′-cyclopenta[ij]isoquinoline]-2,5-dien-4-one, C18H19NO3
  23. The crystal structure of 1,1′-(2,3,5,6-tetramethylpyrazine-1,4-diyl)bis(ethan-1-one), C12H18N2O2
  24. Crystal structure of [μ2-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ2O:O′)] bis(μ2-4,4′-trimethylenedipyridyl-κ2N:N′)disilver(I), C18H24AgN3O4S
  25. Crystal structure of bis ((1-((E)-((4-methoxyphenyl)imino)methyl)naphthalen-2-yl)oxy) copper(II), C36H28CuN2O4
  26. Synthesis and crystal structure of 6,6′-((1E,11E)-5,8-dioxa-2,11-diazadodeca-1,11-diene-1,12-diyl) bis(2,4-di-tert-butylphenol), C36H56N2O4
  27. The crystal structure of barium hexahydroxidoiridate(IV) dihydroxide, Ba2[Ir(OH)6](OH)2
  28. Crystal structure of cinnamoyl ferrocene, C19H16FeO
  29. Crystal structure of (E)-3-(4-butoxyphenyl)acryloylferrocene, C23H24FeO2
  30. Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
  31. The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5
  32. The crystal structure of 1,3,5-trichloro-2-nitrobenzene
  33. The crystal structure of tris(μ2-bromido)-bis(η6-p-cymene)-diosmium(II) tetrafluoroborate, C20H28BBr3F4Os2
  34. Crystal structure of new barium lithium manganese fluorides: Ba14Li1.87Mn14.13F68 with a Jarlite–related structure
  35. Crystal structure of (4-fluorobenzyl)triphenylphosphonium chloride, C25H21ClFP
  36. The crystal structure of calcitriol–chloroform (1/1), C27H44O3⋅CHCl3
  37. The crystal structure of (E)-1-((3)-nitrophenyl)pyren-3-(pyren-1-yl)prop-2-en-1-one, C25H15NO3
  38. Crystal structure of (E)-2-hydroxy-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H16N2O3
  39. Crystal structure of (E)-(3-(thiophen-2-yl)acryloyl)ferrocene, C17H14FeOS
  40. Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2
  41. Synthesis and crystal structure poly[diaqua(μ3-3-(((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl) methyl)ammonio)propanoate-κ3 O:O′:O″) sodium(I)] monohydrate, C20H24NNaO12S
  42. Crystal structure of 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine C19H18N4O2
  43. Synthesis and crystal structure of 4-(difluoromethyl)-1-methyl-N-(pyridin-3-yl)-1H-pyrazole-3-carboxamide hydrate, C11H12F2N4O2
  44. The crystal structure of caesalfurfuric acid B, C22H32O4
  45. The crystal structure of 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone, C12H9Br2N3O3
  46. The crystal structure of bis{chlorido-[μ2-(1-oxidopyridin-2-yl)(pyridin-2-yl)amido-κ3 O,N, N′]copper(II)}, C20H16Cl2Cu2N6O2
  47. The crystal structure of 3-amino-2-formyl-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile, C22H16N2O
  48. The crystal structure of 1,1′-(2,5-dimethylpyrazine-1,4-diyl)bis(ethan-1-one), C10H14N2O2
  49. Crystal structure of 5′-(9-phenyl-9H-carbazol-3-yl)-[2,2′-bithiophene]-5-carbaldehyde, C27H17NOS2
  50. The crystal structure of the double salt dipyridin-1-ium bromide tribromide
  51. Crystal structure of (E)-(3-(3-methylthiophen-2-yl)acryloyl)ferrocene, C18H16FeOS
  52. Crystal structure of (E)-(3-(4-phenoxyphenyl)acryloyl)ferrocene, C25H20FeO2
  53. Crystal structure of (E)-(3-(3,4-dimethylphenyl)acryloyl)ferrocene, C21H20FeO
  54. Crystal structure of [(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N‴)tetracyanidodiplatinum(II)] dimethyl sulfoxide solvate, C18H36N8O2Pt2S2
  55. Crystal structure of (4-ethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO2P
  56. Crystal structure of (1-naphthalen-1-yl-methyl)triphenylphosphonium chloride ethanol solvate, C31H30ClOP
  57. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)platinum(II) bis[tribromido(dimethyl sulfoxide-κS)platinate(II)], C14H36Br6N4O2Pt3S2
  58. Crystal structure of (2-methylbenzyl)triphenylphosphonium chloride ethanol solvate, C28H30ClOP
  59. Crystal structure of bis(η2, σ1-8-methoxycyclooct-4-enyl)(μ2-1,4,8,11-tetraazacyclotetradecane-κ4 N, N′, N″, N‴)diplatinum(II) dibromide, C28H54Br2N4O2Pt2
  60. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetrabromidopalladate(II), C10H24Br4N4Pd2
  61. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) bis[trichlorido(dimethyl sulfoxide-κS)platinate(II)], C14H36Cl6N4O2PdPt2S2
  62. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetraiodidopalladate(II), C10H24I4N4Pd2
https://doi.org/10.1515/ncrs-2024-0380
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Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2
  4. Synthesis and crystal structure of ethyl (2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR,E)-10-(((3,4-dichlorobenzyl)oxy)imino)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate
  5. The crystal structure of pyrazole nitrate
  6. Crystal structure of tetramethyl-bis(μ2-2-(2-hydroxy-3-methoxybenzylidene)-1-(6-(2-(2-hydroxy-3-methoxybenzylidene)hydrazine-1-carbonyl)picolinoyl)hydrazin-1-ido-κ4O,N,O′:O′)ditin(II) ─ ethanol (1/2), C54H62N10O14Sn2
  7. Crystal structure of catena-poly[μ3-iodido-(4-bromopyridine-κ1N)copper(I)], C5H4BrNCuI
  8. The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P
  9. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(phenylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C34H48N2O
  10. The crystal structure of (E)-3-((E)-3-(4-ethoxy-3-methoxyphenyl)-1-hydroxyallylidene) chroman-2,4-dione, C21H18O6
  11. The crystal structure of trans–L/D-[bis-(2-methyl-8-hydroxyquinoline-κ2 N,O) bis-(1,3,5-triaza-7-phosphaadamantane-κ2 P)cobalt(III)] tetrafluoroborate
  12. Crystal structure of 9-chloro-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C14H15ClN4
  13. Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3
  14. The crystal structure of 4–bromo-3,5-dinitropyrazole
  15. Crystal structure of 8-hydroxy-3,5,8a-trimethyl-7,8,8a,9-tetrahydronaphtho[2,3-b]furan-4,6-dione, C15H16O4
  16. Crystal structure of 5-hydroxy-3,5,8a-trimethyl-4a,5,6,7,8a,9-hexahydronaphtho[2,3-b]furan-4,8-dione, C15H18O4
  17. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(p-tolylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C35H50N2O
  18. The crystal structure of catena-poly((μ2-1,3,5-tri(1H- imidazol-1-yl)benzene κ2N:N′)-bis(4-hydroxbenzoato-κ1O)-zinc(II) monohydrate), C29H24N6O7Zn
  19. Crystal structure of 2-(benzo[d]oxazol-2-yl)acetonitrile, C9H6N2O
  20. Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7
  21. The crystal structure of the double salt potassium 1-methylpiperazine-1,4-di-ium trinitrate, C5H14KN5O9
  22. Crystal structure of 5′-hydroxy-6′-methoxy-1′-methyl-2′,3′,8′,8a′-tetrahydro-1′H-spiro[cyclohexane-1,7′-cyclopenta[ij]isoquinoline]-2,5-dien-4-one, C18H19NO3
  23. The crystal structure of 1,1′-(2,3,5,6-tetramethylpyrazine-1,4-diyl)bis(ethan-1-one), C12H18N2O2
  24. Crystal structure of [μ2-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ2O:O′)] bis(μ2-4,4′-trimethylenedipyridyl-κ2N:N′)disilver(I), C18H24AgN3O4S
  25. Crystal structure of bis ((1-((E)-((4-methoxyphenyl)imino)methyl)naphthalen-2-yl)oxy) copper(II), C36H28CuN2O4
  26. Synthesis and crystal structure of 6,6′-((1E,11E)-5,8-dioxa-2,11-diazadodeca-1,11-diene-1,12-diyl) bis(2,4-di-tert-butylphenol), C36H56N2O4
  27. The crystal structure of barium hexahydroxidoiridate(IV) dihydroxide, Ba2[Ir(OH)6](OH)2
  28. Crystal structure of cinnamoyl ferrocene, C19H16FeO
  29. Crystal structure of (E)-3-(4-butoxyphenyl)acryloylferrocene, C23H24FeO2
  30. Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
  31. The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5
  32. The crystal structure of 1,3,5-trichloro-2-nitrobenzene
  33. The crystal structure of tris(μ2-bromido)-bis(η6-p-cymene)-diosmium(II) tetrafluoroborate, C20H28BBr3F4Os2
  34. Crystal structure of new barium lithium manganese fluorides: Ba14Li1.87Mn14.13F68 with a Jarlite–related structure
  35. Crystal structure of (4-fluorobenzyl)triphenylphosphonium chloride, C25H21ClFP
  36. The crystal structure of calcitriol–chloroform (1/1), C27H44O3⋅CHCl3
  37. The crystal structure of (E)-1-((3)-nitrophenyl)pyren-3-(pyren-1-yl)prop-2-en-1-one, C25H15NO3
  38. Crystal structure of (E)-2-hydroxy-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H16N2O3
  39. Crystal structure of (E)-(3-(thiophen-2-yl)acryloyl)ferrocene, C17H14FeOS
  40. Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2
  41. Synthesis and crystal structure poly[diaqua(μ3-3-(((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl) methyl)ammonio)propanoate-κ3 O:O′:O″) sodium(I)] monohydrate, C20H24NNaO12S
  42. Crystal structure of 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine C19H18N4O2
  43. Synthesis and crystal structure of 4-(difluoromethyl)-1-methyl-N-(pyridin-3-yl)-1H-pyrazole-3-carboxamide hydrate, C11H12F2N4O2
  44. The crystal structure of caesalfurfuric acid B, C22H32O4
  45. The crystal structure of 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone, C12H9Br2N3O3
  46. The crystal structure of bis{chlorido-[μ2-(1-oxidopyridin-2-yl)(pyridin-2-yl)amido-κ3 O,N, N′]copper(II)}, C20H16Cl2Cu2N6O2
  47. The crystal structure of 3-amino-2-formyl-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile, C22H16N2O
  48. The crystal structure of 1,1′-(2,5-dimethylpyrazine-1,4-diyl)bis(ethan-1-one), C10H14N2O2
  49. Crystal structure of 5′-(9-phenyl-9H-carbazol-3-yl)-[2,2′-bithiophene]-5-carbaldehyde, C27H17NOS2
  50. The crystal structure of the double salt dipyridin-1-ium bromide tribromide
  51. Crystal structure of (E)-(3-(3-methylthiophen-2-yl)acryloyl)ferrocene, C18H16FeOS
  52. Crystal structure of (E)-(3-(4-phenoxyphenyl)acryloyl)ferrocene, C25H20FeO2
  53. Crystal structure of (E)-(3-(3,4-dimethylphenyl)acryloyl)ferrocene, C21H20FeO
  54. Crystal structure of [(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N‴)tetracyanidodiplatinum(II)] dimethyl sulfoxide solvate, C18H36N8O2Pt2S2
  55. Crystal structure of (4-ethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO2P
  56. Crystal structure of (1-naphthalen-1-yl-methyl)triphenylphosphonium chloride ethanol solvate, C31H30ClOP
  57. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)platinum(II) bis[tribromido(dimethyl sulfoxide-κS)platinate(II)], C14H36Br6N4O2Pt3S2
  58. Crystal structure of (2-methylbenzyl)triphenylphosphonium chloride ethanol solvate, C28H30ClOP
  59. Crystal structure of bis(η2, σ1-8-methoxycyclooct-4-enyl)(μ2-1,4,8,11-tetraazacyclotetradecane-κ4 N, N′, N″, N‴)diplatinum(II) dibromide, C28H54Br2N4O2Pt2
  60. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetrabromidopalladate(II), C10H24Br4N4Pd2
  61. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) bis[trichlorido(dimethyl sulfoxide-κS)platinate(II)], C14H36Cl6N4O2PdPt2S2
  62. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetraiodidopalladate(II), C10H24I4N4Pd2
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Heruntergeladen am 14.10.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2024-0380/html?lang=de
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