Startseite Crystal structure of 6,8-diphenyl-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(3H)-one, C27H20FNO
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Crystal structure of 6,8-diphenyl-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(3H)-one, C27H20FNO

  • Marole M. Maluleka , Felix A. Oyeyiola und Malose J. Mphahlele EMAIL logo
Veröffentlicht/Copyright: 4. März 2017
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 232 Heft 3

Abstract

C27H20FNO, monoclinic, P21/n (no. 14), a = 13.1620 Å, b = 13.8779 Å, c = 11.1618 Å, β = 99.710(1)°, V = 2009.62(6) Å3, Z = 4, Rgt(F) = 0.0436, wRref(F2) = 0.1310, T = 173(2) K.

CCDC no.:: 1530864

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Yellow block
Size:0.46 × 0.43 × 0.11 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.9 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω scans
2θmax, completeness:56°, >99%
N(hkl)measured, N(hkl)unique, Rint:25349, 4862, 0.071
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3566
N(param)refined:275
Programs:Bruker programs [1], SHELX [2], PLATON [3–4]
Table 2

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

AtomxyzUiso*/Ueq
C11.08261(9)0.87850(9)0.41526(10)0.0289(3)
C21.17171(10)0.90592(9)0.36769(10)0.0311(3)
C31.25833(10)0.93585(9)0.44637(10)0.0328(3)
H31.31760.95400.41350.039*
C41.26273(10)0.94058(9)0.57288(10)0.0314(3)
C51.17516(10)0.91407(9)0.61790(10)0.0313(3)
H51.17600.91640.70310.038*
C61.08569(9)0.88402(9)0.54193(10)0.0292(3)
C70.99421(10)0.85745(9)0.59438(11)0.0327(3)
C80.89689(10)0.84094(10)0.50465(11)0.0351(3)
H8A0.86240.90360.48380.042*
H8B0.84950.80010.54280.042*
C90.91765(10)0.79226(10)0.38812(11)0.0342(3)
H90.94530.72610.40850.041*
C100.81990(10)0.78413(10)0.29418(11)0.0347(3)
C110.75634(11)0.70484(12)0.29512(13)0.0461(4)
H110.77480.65570.35390.055*
C120.66576(12)0.69599(13)0.21132(15)0.0520(4)
H120.62210.64160.21230.062*
C130.64132(11)0.76773(12)0.12755(13)0.0438(4)
C140.70189(11)0.84705(11)0.12228(13)0.0425(3)
H140.68310.89530.06230.051*
C150.79166(11)0.85511(10)0.20713(12)0.0377(3)
H150.83450.91010.20560.045*
C161.17435(10)0.89780(10)0.23490(11)0.0350(3)
C171.12024(15)0.96057(18)0.15243(15)0.0726(6)
H171.07991.01030.17930.087*
C181.12499(16)0.9508(2)0.02920(16)0.0955(9)
H181.08710.9939−0.02760.115*
C191.18271(15)0.88077(17)−0.01086(14)0.0701(6)
H191.18520.8753−0.09510.084*
C201.23712(16)0.81826(13)0.06951(14)0.0607(5)
H201.27780.76920.04170.073*
C211.23267(13)0.82689(11)0.19263(13)0.0482(4)
H211.27050.78310.24870.058*
C221.35742(10)0.97269(10)0.65462(11)0.0335(3)
C231.41426(11)1.05112(11)0.62505(12)0.0410(3)
H231.39341.08380.55010.049*
C241.50092(11)1.08207(12)0.70378(14)0.0476(4)
H241.53851.13620.68290.057*
C251.53311(11)1.03461(13)0.81255(14)0.0491(4)
H251.59281.05580.86600.059*
C261.47814(11)0.95644(12)0.84296(13)0.0453(4)
H261.50000.92370.91760.054*
C271.39090(10)0.92552(11)0.76470(11)0.0389(3)
H271.35350.87150.78630.047*
N10.99530(8)0.84800(8)0.33891(10)0.0342(3)
O10.99674(8)0.85217(8)0.70421(8)0.0477(3)
F10.55246(7)0.75914(8)0.04504(9)0.0631(3)
H11.0078(13)0.8267(12)0.2691(16)0.054(5)*

Source of material

A mixture of 6,8-dibromo-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (1.0 mmol), phenylboronic acid (2.2 mmol), dichlorido-bis(triphenylphosphine)palladium(II) (0.05 mmol), tricyclohexylphosphine (0.1 mmol) and potassium carbonate (2.0 mmol) in a dioxane-water mixture (3:1, v/v) was purged with argon for 0.5 h. A balloon filled with argon gas was then connected to the top of the condenser and the mixture was heated with stirring at 80–90 °C under argon atmosphere for 3 h. The mixture was quenched with ice cold water and the product extracted with chloroform. The combined organic extracts were sequentially washed with brine, dried over anhyd. MgSO4, filtered and then evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel to afford the title compound [5]. Single crystals were obtained by slow evaporation of ethanol at room temperature.

Experimental details

The collection method involved ω-scans of width 0.3°. Data reduction was carried out using the program SAINT+[1] and absorption corrections were made using the program SADABS [1]. The crystal structure was solved by direct methods using SHELXTL [2]. Hydrogen atoms were positioned geometrically and allowed to ride on their respective parent atoms. Aromatic C—H distances were set to 0.93 Å and their Uiso set to 1.2 times the Ueq for the atoms to which they are bonded. Hydrogen atoms involved in hydrogen bonding were refined freely.

Comment

In recent years, there has been growing interest in the design and synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones due to their wide range of biological properties [6]. 2-Aryl-2,3-dihydroquinolin-4(1H)-one derivatives serve as antitumor agents [7] and others exhibit microRNA inhibitory properties [8]. The synthesis of the title compound follows the transition metal catalysed Suzuki-Miyaura cross coupling reaction as a tool for carbon-carbon bond formation. The crystal structure of the analogous 2,3-diphenylquinoline showed that the quinolone ring was essentially planar [9]. The heterocyclic ring of the title compound exists in half-chair conformation. The 2-aryl ring is twisted from co-planarity expressed by a torsion angle of 91.70° for [C(8)—C(9)—C(10)—C(15)]. The 6- and 8-aryl rings are also turned out of the plane of the heterocyclic moiety with average torsion angels of −110° and −139°, respectively. The crystal structure shows an intermolecular hydrogen bond between N—H of one molecule and the carbonyl oxygen of another one with a D—H⋅⋅⋅A angle of 124° and H⋅⋅⋅A distance of 2.58 Å.

Acknowledgement

The authors are grateful to the University of South Africa and national research foundation (NRF) for financial assistance and M. A. Fernandes at Witwatersrand University for X-ray data.

References

1 Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, WI, USA (2013).Suche in Google Scholar

2 Sheldrick, G. M.: A Short History of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Suche in Google Scholar

3 Farrugia, L. J.: WinGX suite for small-molecule single-crystal crystallography. J. Appl. Cryst. 32 (1999) 837–838.10.1107/S0021889899006020Suche in Google Scholar

4 Spek, A. L.: Structure validation in chemical crystallography. Acta Crystallogr. D65 (2009) 148–155.10.1107/S090744490804362XSuche in Google Scholar

5 Mphahlele, M. J.; Oyeyiola F. A.: Suzuki-Miyaura cross-coupling of 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones and subsequent dehydrogenation and oxidative aromatization of the resulting 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones. Tetrahedron 67 (2011) 6819–6825.10.1016/j.tet.2011.06.085Suche in Google Scholar

6 Zhang, S.-X.; Feng, J.; Kuo, S.-C.; Brossi, A.; Hamel, E.; Tropsha, A.; Lee, K.-H.: Antitumor agents. 199. Three-dimensional quantitative structure-activity relationship study of the colchicine binding site ligands using comparative molecular field analysis. J. Med. Chem. 43 (2000) 167–176.10.1021/jm990333aSuche in Google Scholar

7 Xia, Y.; Yang, Z.-Y.; Xia, P.; Batow, K. F.; Tachibana, Y.; Kuo, S.-C.; Hamel, E.; Hackl, GT.; Lee, K.-H.: Synthesis and biological evaluation of 6,7,2′,3′,4′-substituted-1,2,3,4-tetrahydro-2-phenyl-4-quinolones as a new class of antimitotic antitumor agents. J. Med. Chem. 41 (1988) 1155–1162.10.1021/jm9707479Suche in Google Scholar

8 Chandrasekhar, S.; Pushpavalli, S. N. C. V. L.; Chatla, S.; Mukhopadhyay, D.; Changanna, B.; Vijeender, K.; Srihari, P.; Reddy, C. R.; Ramaiah, M. J.; Bhadra, U.: Aza-flavanones as potent cross-species microRNA inhibitors that arrest cell cycle. Bioorg. Med. Chem. Lett. 22 (2012) 645–648.10.1016/j.bmcl.2011.10.061Suche in Google Scholar

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Received: 2016-9-20
Accepted: 2017-2-7
Published Online: 2017-3-4
Published in Print: 2017-5-24

©2017 Marole M. Maluleka et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of 2,5-diiodo-4-nitro-1H-imidazole hemihydrate, C6H4I4N6O5
  3. Crystal structure of catena-poly[μ2-2,2′-(1,3-phenylene)diacetato-κ4O,O′:O′′,O′′′)-(μ2-1,6-bis(2-methyl-1H-benzo[d]imidazol-1-yl)hexane-κ2N:N′)cadmium(II)], C32H34CdN4O4
  4. Crystal structure of poly[aqua-(2,2′-bipyridine-κN,N′)-(μ4-5,5′-(hexane-1,6-diyl)-bis(oxy)diisophthalato κ8O1,O2:O3,O4:O5,O6:O7,O8)manganese(II)], C21H21MnN2O7
  5. Crystal structure of poly-[(μ2-((1,3-bis(benzimidazol-1-yl)propane-κ2N:N′)(μ2-4-tert-butyl-phthalato-κ2O:O′)cobalt(II)] monohydrate, C29H30CoN4O5
  6. Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-5-(oxo-5,6,7,8-tetrahydro-4H-chromene)-3-carbonitrile – ethanol (1/1), C21H26N2O6
  7. Crystal structure of ethyl 1-benzyl-5-phenyl-1H-pyrazole-3-carboxylate, C19H18N2O2
  8. Crystal structure of 2-(1-benzyl-3-phenyl-1H-pyrazol-5-yl)-5-(4-nitrobenzylthio)-1,3,4-oxadiazole, C25H19N5O3S
  9. Structure and photochromism of 1,2-bis[2-methyl-5-(2-chlorophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16Cl2F6S2
  10. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-4-ylmethylene)aniline, C18H22N2
  11. Crystal structure of (E)-2,4-dibromo-6-(((4-methyl-2-nitrophenyl)imino) methyl)phenol, C10H14Br2N2O3
  12. Crystal structure of (bis(2,2′-bipyridine-κ2N,N′))-(3,5-dinitrosalicylato-κ2O,O′)nickel(II), C27H18N6NiO7
  13. Crystal structure of 1-(diethoxy phosphonomethyl) 2-benzoyl-3-chloro-2-cyclohexen-1-ol, C18H24ClO5P
  14. Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C22H27CuN4O12.50
  15. Crystal structure of 1α,11-dihydroxyeremophil-9-en-8-one, C15H24O3
  16. Crystal structure of 1-ferrocenylsulfonyl-1H-imidazo[4,5-b]pyridine, C16H13FeN3O2S
  17. Crystal structure of bis(μ2-azido-κ2N:N)-dichlorido-bis(μ2-2-(pyridin-2-yl)ethan-1-ol-κ2O,N)dicopper(II), C14H18Cl2Cu2N8O2
  18. Crystal structure of (5,15-cis-bis(2-hydroxy-1-naphthyl)-10-phenyl-20-(4-hydroxyphenyl)-porphyrinato)-(pyridine)-zinc(ii) pyridine solvate, C67H47N7O3Zn
  19. Crystal structure of (μ2-[2,2′-bis(diphenylphosphino)-1,1′-binaphthalene oxide-κ2O,P])-iodido copper(I), C44H32CuIOP2
  20. Crystal structure of 6,8-diphenyl-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(3H)-one, C27H20FNO
  21. Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C68H104O4
  22. Crystal structure of N,N′–bis(pyridin-4-ylmethyl)pyrazine-2,3-dicarboxamide dihydrate, C18H20N6O4
  23. Crystal structure of a diaqua-bis(3,5-di(1H-imidazol-1-yl)pyridine-κN)-bis(2-(4-carboxy-phenyl)acetato-κO]manganese(II), C40H36MnN10O10
  24. Crystal structure of 4-(4-hydroxy-3-methoxy-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester, C21H25NO5
  25. Crystal structure of (E)-4,4′-(ethene-1,2-diyl)bis(3-nitrobenzoic acid) 1.5 hydrate, C16H13N2O9.5
  26. Crystal structure of (E)-2-(5-(4-fluorophenyl)-3-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-5-((4-fluorophenyl)diazenyl)-4-methylthiazole, C23H17F2N5OS
  27. Crystal structure of the co-crystalline adduct 4-((4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide - acetic acid (1/1), C21H24N4O4S ⋅ C2H4O2
  28. Synthesis and crystal structure of 2-((5-chlorobenzo[c][1,2,5]thiadiazol-4-yl)amino)-4,5-dihydro-1H-imidazol-3-ium tetraphenylborate, C33H29BClN5S
  29. Crystal structure of (4-chlorophenyl)(3-ferrocenyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)methanone, C21H14ClF3FeN2O
  30. Crystal structure of (S)-benzyl 3-(benzylcarba-moyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate, C25H24N2O3
  31. Crystal structure of 5-acetyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one, C15H17FN2O4
  32. Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16FIN2
  33. Crystal structure of methyl 1H-indole-2-carboxylate, C10H9NO2
  34. Crystal structure of 2,3-diphenyl-1-[(dipropylamino)acetyl]-1,3-diazaspiro[4.5]decan-4-one, C28H37N3O2
  35. Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3
  36. Crystal structure of 2,9-dibromo-1,10-phenanthroline, C12H6Br2N2
  37. Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S
  38. Crystal structure of trans-bis((E)-7-oxo-4-(phenyldiazenyl)cyclohepta-1,3,5-trien-1-olato)-κ2O,O′)-bis(pyridine-κN)cobalt(II), C36H28CoN6O4
  39. Crystal structure of 2-(4-methyl-3-phenylthiazol-2(3H)-ylidene)malononitrile, C13H9N3S
  40. Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C24H27ClN2S
  41. Crystal structure of chlorido{[3-(η5-cyclopenta-dienyl)-2,2,3-trimethyl-1-phenylbutylidene] azanido-κN}[η2(N,O)-N,N-dimethylhydroxylaminato]titanium(IV), C20H27ClN2OTi
  42. Crystal Structure of 1,1′-dimethyl-[4,4′-bipyridine]-1,1′-diium tetrachloridozincate(II), C12H14Cl4N2Zn
  43. Crystal structure of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde, C11H12N2O3
  44. Crystal structure of 2,3-diphenyl-1-(morpholin-4-ylacetyl)-1,3-diazaspiro[4.5]decan-4-one, C26H31N3O3
  45. Crystal structure of 3,3-dimethyl-3,4-dihydro-1H-benzo[c]chromene-1,6(2H)-dione, C15H14O3
  46. Crystal structure of bis(2-(2-hydroxymethyl)pyridine-κ2N,O)-bis(pivalato-κO)nickel(II), C22H32N2NiO6
  47. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(1H-pyrazole-3-carboxylato-κ2N,O)manganese(II) trihydrate, C20H20N6O7Mn
  48. The crystal structure of 3-aminopropan-1-aminium iodide, C3H11N2I
  49. Crystal structure of ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4 carboxylate, C12H12ClN3O2
  50. Crystal structure of 4,4′-((1Z,1′Z)-2,2′-(2,5-diethoxy-1,4-phenylene)bis(ethene-2,1-diyl))dipyridine, C24H24N2O2
  51. Crystal structure of (16S)-12,16-epoxy-11,14-dihydroxy-17(15/16)-abeo-3a,18-cyclo-8,11,13-abietatrien-7-one, C20H24O4
  52. Crystal structure of aquadichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N,N′,N′′)nickel(II) monohydrate, C18H16Cl2N6NiO2
  53. Crystal structure of catena-poly[dichlorido-(μ-ethane-1,2-diyl-bis-(pyridyl-4-carboxylate-κN:N′)mercury(II)], C15H14Cl2HgN2O4
  54. Crystal structure of methyl 2-acetamido-5-chlorbenzoate, C10H10ClNO3
  55. Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8
  56. Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  57. Crystal structure of 4-(2-ammonioethyl)morpholin-4-ium dichloride monohydrate, C6H18Cl2N2O2
  58. Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2
  59. Crystal structure of 2-(4-(dimethylamino)-2-fluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol monohydrate, C15H20FN7O2
  60. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
  61. Crystal structure of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, C10H16
https://doi.org/10.1515/ncrs-2016-0283
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Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of 2,5-diiodo-4-nitro-1H-imidazole hemihydrate, C6H4I4N6O5
  3. Crystal structure of catena-poly[μ2-2,2′-(1,3-phenylene)diacetato-κ4O,O′:O′′,O′′′)-(μ2-1,6-bis(2-methyl-1H-benzo[d]imidazol-1-yl)hexane-κ2N:N′)cadmium(II)], C32H34CdN4O4
  4. Crystal structure of poly[aqua-(2,2′-bipyridine-κN,N′)-(μ4-5,5′-(hexane-1,6-diyl)-bis(oxy)diisophthalato κ8O1,O2:O3,O4:O5,O6:O7,O8)manganese(II)], C21H21MnN2O7
  5. Crystal structure of poly-[(μ2-((1,3-bis(benzimidazol-1-yl)propane-κ2N:N′)(μ2-4-tert-butyl-phthalato-κ2O:O′)cobalt(II)] monohydrate, C29H30CoN4O5
  6. Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-5-(oxo-5,6,7,8-tetrahydro-4H-chromene)-3-carbonitrile – ethanol (1/1), C21H26N2O6
  7. Crystal structure of ethyl 1-benzyl-5-phenyl-1H-pyrazole-3-carboxylate, C19H18N2O2
  8. Crystal structure of 2-(1-benzyl-3-phenyl-1H-pyrazol-5-yl)-5-(4-nitrobenzylthio)-1,3,4-oxadiazole, C25H19N5O3S
  9. Structure and photochromism of 1,2-bis[2-methyl-5-(2-chlorophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16Cl2F6S2
  10. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-4-ylmethylene)aniline, C18H22N2
  11. Crystal structure of (E)-2,4-dibromo-6-(((4-methyl-2-nitrophenyl)imino) methyl)phenol, C10H14Br2N2O3
  12. Crystal structure of (bis(2,2′-bipyridine-κ2N,N′))-(3,5-dinitrosalicylato-κ2O,O′)nickel(II), C27H18N6NiO7
  13. Crystal structure of 1-(diethoxy phosphonomethyl) 2-benzoyl-3-chloro-2-cyclohexen-1-ol, C18H24ClO5P
  14. Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C22H27CuN4O12.50
  15. Crystal structure of 1α,11-dihydroxyeremophil-9-en-8-one, C15H24O3
  16. Crystal structure of 1-ferrocenylsulfonyl-1H-imidazo[4,5-b]pyridine, C16H13FeN3O2S
  17. Crystal structure of bis(μ2-azido-κ2N:N)-dichlorido-bis(μ2-2-(pyridin-2-yl)ethan-1-ol-κ2O,N)dicopper(II), C14H18Cl2Cu2N8O2
  18. Crystal structure of (5,15-cis-bis(2-hydroxy-1-naphthyl)-10-phenyl-20-(4-hydroxyphenyl)-porphyrinato)-(pyridine)-zinc(ii) pyridine solvate, C67H47N7O3Zn
  19. Crystal structure of (μ2-[2,2′-bis(diphenylphosphino)-1,1′-binaphthalene oxide-κ2O,P])-iodido copper(I), C44H32CuIOP2
  20. Crystal structure of 6,8-diphenyl-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(3H)-one, C27H20FNO
  21. Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C68H104O4
  22. Crystal structure of N,N′–bis(pyridin-4-ylmethyl)pyrazine-2,3-dicarboxamide dihydrate, C18H20N6O4
  23. Crystal structure of a diaqua-bis(3,5-di(1H-imidazol-1-yl)pyridine-κN)-bis(2-(4-carboxy-phenyl)acetato-κO]manganese(II), C40H36MnN10O10
  24. Crystal structure of 4-(4-hydroxy-3-methoxy-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester, C21H25NO5
  25. Crystal structure of (E)-4,4′-(ethene-1,2-diyl)bis(3-nitrobenzoic acid) 1.5 hydrate, C16H13N2O9.5
  26. Crystal structure of (E)-2-(5-(4-fluorophenyl)-3-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-5-((4-fluorophenyl)diazenyl)-4-methylthiazole, C23H17F2N5OS
  27. Crystal structure of the co-crystalline adduct 4-((4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide - acetic acid (1/1), C21H24N4O4S ⋅ C2H4O2
  28. Synthesis and crystal structure of 2-((5-chlorobenzo[c][1,2,5]thiadiazol-4-yl)amino)-4,5-dihydro-1H-imidazol-3-ium tetraphenylborate, C33H29BClN5S
  29. Crystal structure of (4-chlorophenyl)(3-ferrocenyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)methanone, C21H14ClF3FeN2O
  30. Crystal structure of (S)-benzyl 3-(benzylcarba-moyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate, C25H24N2O3
  31. Crystal structure of 5-acetyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one, C15H17FN2O4
  32. Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16FIN2
  33. Crystal structure of methyl 1H-indole-2-carboxylate, C10H9NO2
  34. Crystal structure of 2,3-diphenyl-1-[(dipropylamino)acetyl]-1,3-diazaspiro[4.5]decan-4-one, C28H37N3O2
  35. Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3
  36. Crystal structure of 2,9-dibromo-1,10-phenanthroline, C12H6Br2N2
  37. Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S
  38. Crystal structure of trans-bis((E)-7-oxo-4-(phenyldiazenyl)cyclohepta-1,3,5-trien-1-olato)-κ2O,O′)-bis(pyridine-κN)cobalt(II), C36H28CoN6O4
  39. Crystal structure of 2-(4-methyl-3-phenylthiazol-2(3H)-ylidene)malononitrile, C13H9N3S
  40. Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C24H27ClN2S
  41. Crystal structure of chlorido{[3-(η5-cyclopenta-dienyl)-2,2,3-trimethyl-1-phenylbutylidene] azanido-κN}[η2(N,O)-N,N-dimethylhydroxylaminato]titanium(IV), C20H27ClN2OTi
  42. Crystal Structure of 1,1′-dimethyl-[4,4′-bipyridine]-1,1′-diium tetrachloridozincate(II), C12H14Cl4N2Zn
  43. Crystal structure of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde, C11H12N2O3
  44. Crystal structure of 2,3-diphenyl-1-(morpholin-4-ylacetyl)-1,3-diazaspiro[4.5]decan-4-one, C26H31N3O3
  45. Crystal structure of 3,3-dimethyl-3,4-dihydro-1H-benzo[c]chromene-1,6(2H)-dione, C15H14O3
  46. Crystal structure of bis(2-(2-hydroxymethyl)pyridine-κ2N,O)-bis(pivalato-κO)nickel(II), C22H32N2NiO6
  47. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(1H-pyrazole-3-carboxylato-κ2N,O)manganese(II) trihydrate, C20H20N6O7Mn
  48. The crystal structure of 3-aminopropan-1-aminium iodide, C3H11N2I
  49. Crystal structure of ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4 carboxylate, C12H12ClN3O2
  50. Crystal structure of 4,4′-((1Z,1′Z)-2,2′-(2,5-diethoxy-1,4-phenylene)bis(ethene-2,1-diyl))dipyridine, C24H24N2O2
  51. Crystal structure of (16S)-12,16-epoxy-11,14-dihydroxy-17(15/16)-abeo-3a,18-cyclo-8,11,13-abietatrien-7-one, C20H24O4
  52. Crystal structure of aquadichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N,N′,N′′)nickel(II) monohydrate, C18H16Cl2N6NiO2
  53. Crystal structure of catena-poly[dichlorido-(μ-ethane-1,2-diyl-bis-(pyridyl-4-carboxylate-κN:N′)mercury(II)], C15H14Cl2HgN2O4
  54. Crystal structure of methyl 2-acetamido-5-chlorbenzoate, C10H10ClNO3
  55. Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8
  56. Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  57. Crystal structure of 4-(2-ammonioethyl)morpholin-4-ium dichloride monohydrate, C6H18Cl2N2O2
  58. Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2
  59. Crystal structure of 2-(4-(dimethylamino)-2-fluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol monohydrate, C15H20FN7O2
  60. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
  61. Crystal structure of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, C10H16
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Heruntergeladen am 22.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2016-0283/html?lang=de
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