Startseite Crystal structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate, C19H16FNO2
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Crystal structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate, C19H16FNO2

  • Hong-Yu Song ORCID logo , Shan Liu , Bo-Nan Zhang , Qi-Di Zhong ORCID logo und Ya-Juan Qi EMAIL logo
Veröffentlicht/Copyright: 14. Juli 2021

Abstract

C19H16FNO2, monoclinic, P21/c (no. 14), a = 10.805(7) Å, b = 20.984(13) Å, c = 7.034(4) Å, β = 93.386(13)°, V = 1592.0(17), Z = 4, R gt (F) = 0.0561, wR ref (F2) = 0.1336, T = 296 K.

CCDC no.: 2086189

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colorless block
Size: 0.16 × 0.15 × 0.11 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 25.3°, 99%
N(hkl)measured, N(hkl)unique, Rint: 8298, 2872, 0.100
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1176
N(param)refined: 209
Programs: Bruker [1], SHELX [2], [3]
Table 2:

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

Atom x y z Uiso*/Ueq
F1 0.08821 (19) 0.94114 (9) 0.6579 (4) 0.1137 (9)
O1 0.3590 (2) 0.54947 (9) 0.7370 (4) 0.0748 (8)
O3 0.5604 (2) 0.53342 (11) 0.7188 (5) 0.1033 (11)
N1 0.4073 (2) 0.73707 (12) 0.6656 (4) 0.0525 (7)
C1 0.2056 (3) 0.47106 (16) 0.7586 (7) 0.1127 (16)
H1A 0.165475 0.487932 0.644082 0.169*
H1B 0.174638 0.492310 0.866947 0.169*
H1C 0.188933 0.426231 0.766606 0.169*
C2 0.3403 (3) 0.48132 (14) 0.7560 (6) 0.0916 (14)
H2A 0.381793 0.465835 0.873015 0.110*
H2B 0.373350 0.458866 0.649638 0.110*
C3 0.4750 (3) 0.56910 (15) 0.7192 (5) 0.0616 (10)
C4 0.4804 (3) 0.63826 (14) 0.6979 (5) 0.0522 (9)
C5 0.3776 (3) 0.67587 (14) 0.7041 (5) 0.0545 (9)
H5 0.299056 0.661607 0.730842 0.065*
C6 0.5317 (3) 0.73920 (15) 0.6342 (4) 0.0547 (9)
H6 0.575693 0.775670 0.605173 0.066*
C7 0.5802 (3) 0.67952 (15) 0.6524 (5) 0.0521 (9)
C8 0.7122 (3) 0.66549 (15) 0.6289 (5) 0.0552 (9)
C9 0.7787 (3) 0.62076 (15) 0.7381 (5) 0.0688 (11)
H9 0.738598 0.597624 0.828955 0.083*
C10 0.9025 (3) 0.60973 (16) 0.7153 (6) 0.0835 (13)
H10 0.944565 0.578886 0.788765 0.100*
C11 0.9642 (3) 0.64440 (19) 0.5836 (7) 0.0836 (13)
H11 1.047744 0.636971 0.567454 0.100*
C12 0.9013 (3) 0.68970 (17) 0.4774 (6) 0.0811 (13)
H12 0.942507 0.713507 0.389245 0.097*
C13 0.7773 (3) 0.70039 (15) 0.4999 (6) 0.0664 (10)
H13 0.736149 0.731695 0.427043 0.080*
C14 0.3248 (3) 0.79007 (14) 0.6631 (5) 0.0509 (9)
C15 0.3675 (3) 0.84927 (15) 0.7224 (5) 0.0640 (10)
H15 0.450186 0.854587 0.764073 0.077*
C16 0.2877 (4) 0.90032 (15) 0.7198 (5) 0.0735 (11)
H16 0.315288 0.940566 0.758146 0.088*
C17 0.1669 (4) 0.89030 (19) 0.6595 (6) 0.0738 (12)
C18 0.1225 (3) 0.83312 (18) 0.6009 (6) 0.0744 (12)
H18 0.039409 0.828208 0.561026 0.089*
C19 0.2024 (3) 0.78235 (15) 0.6012 (5) 0.0611 (10)
H19 0.173874 0.742631 0.559539 0.073*

Source of material

A 500 mL round-bottom flask was sequentially filled with 3.33 g (30 mmol) 4-fluoroaniline, 2.94 g (30 mmol) ethyl propiolate, 3.96 g (30 mmol) cinnamaldehyde, 1.03 g (12 mmol) piperazine, 0.04 g (0.24 mmol) p-toluenesulfonic acid and 200 mL 1,2-dichloroethane. The mixture was slowly heated to 356 K for 12 h. After the reaction, the mixture was cooled to room temperature. Two-hundred milliliters of water were slowly added, extracted with ethyl acetate for three times (100 mL/time), the organic layer was separated, washed with saturated sodium chloride solution for two times (100 mL/time), and the organic layers were combined. Dry with anhydrous sodium sulfate, filter, distill under reduced pressure to remove the solvent, and separate by silica gel column chromatography (ethyl acetate: petroleum ether = 1:50) to obtain a white powdery solid. The solid is exposed to 410 nm ultraviolet light and normal temperature light. After 24 h, the final product was obtained.

Experimental details

All hydrogen atoms were placed in the calculated positions and all the non-hydrogen atoms were refined anisotropically.

Comment

Natural products have inspired the synthesis of compounds for pharmaceutical application, most of which are based on N-heterocyclic motifs [4]. The powerful pharmaceutical and pharmacological features provided by the pyrrole nucleus as pharmacophore unit of many drugs are still recognized by medicinal chemists [5], [6]. Photochemical reactions have been widely used in various synthetic reactions [7], [8]. This time, a new pyrrole compound was obtained by light irradiation using different reaction solvents.

In the molecules of the title crystal structure, the pyrrole ring and the aryl moieties are not in one plane. The dihedral angle of the ring formed by C14–19 and the pyrrole ring formed by N1–C7 is 59.8°. The dihedral angle between the benzene ring formed by C8–13 and the pyrrole ring formed by N1–C7 is 49.0°. The bond lengths and angles are in the expected ranges [9].


Corresponding author: Ya-Juan Qi, School of Basic Medical Sciences, North China University of Science and Technology, 063210 Caofeidian District, Tangshan, P. R. China, E-mail:

Funding source: Hebei Provincial Natural Science Foundation of China

Award Identifier / Grant number: C2020209081

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

  2. Research funding: The Project Supported by Hebei Provincial Natural Science Foundation of China (C2020209081).

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

References

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Received: 2021-05-31
Accepted: 2021-06-28
Published Online: 2021-07-14
Published in Print: 2021-09-27

© 2021 Hong-Yu Song et al., 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. Crystal structure of [aqua-(4-iodopyridine-2,6-dicarboxylato-κ3 O,N,O′)-(1,10-phenanothroline-κ2 N,N′)copper(II)] dihydrate, C19H16O7N3CuI
  4. The crystal structure of tetrakis(1-isopropyl-1H-imidazolium) octamolybdate, C24H44Mo8N8O26
  5. Crystal structure of catena-poly[bis(µ2-3,5-bis(1-imidazolyl)pyridine-κ2 N:N′)-(µ2-3-nitrophthalato-k3 O,O′:O″)cadmium(II)] dihydrate, C30H25N11O8Cd
  6. The crystal structure of diaqua-bis(2-(3-(1H-pyrazol-4-yl)-1H-1,2,4-triazol-5-yl)pyridine-κ2 N:N′)-bis(3,5-dicarboxybenzoato-κ1 O)cobalt(II), C38H30CoN12O14
  7. Crystal structure of the nickel(II) complex aqua-(2,6-di(pyrazin-2-yl)-4,4′-bipyridine-κ3 N,N′,N′′)-(phthalato-κ2 O,O′)nickel(II) tetrahydrate, C26H26N6O9Ni
  8. The crystal structure of 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]-N-methylmethanaminium 3-carboxyprop-2-enoate, C21H20FN3O6S
  9. The crystal structure of 1,2-bis(4-pyridyl)ethane - 4,4-dihydroxydiphenylmethane (1/1), C25H21N2O2
  10. Crystal structure of bis(2-((E)-5-chloro-2-hydroxybenzylidene)hydrazineyl)methaniminium trifluoroacetate dihydrate, C34H36Cl4N10O12
  11. Crystal structure of 1-cyclopropyl-7-ethoxy-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C15H13F2NO4
  12. Crystal structure of methyl 3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)benzoate, C18H15BN2O2
  13. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-2-hydroxybenzohydrazide, C14H11ClN2O3
  14. Crystal structure of Al-rich fluorophlogopite, K1.0(Mg2.8Al0.2)(Si2.8Al1.2)O10F2
  15. The crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium hexafluoridoantimonate(V), C20H22F6I2N3Sb
  16. Crystal structure of tris(3-iodopyridin-1-ium) catena-poly[(hexachlorido-κ1 Cl)-(μ2-trichlorido-κ2 Cl:Cl)diantimony(III)], C15H15Cl9I3N3Sb2
  17. Crystal structure of methyl 2-(1H-naphtho[1,8-de][1.3.2]diazaborinin-2(3H-yl)benzoate C18H15BN2O2
  18. The crystal structure of 1,8-bis(4-methoxybenzoyl)naphthalene-2,7-diyl dibenzoate, C40H28O8
  19. Crystal structure of 2-bromo-1,3,6,8-tetramethylBOPHY (BOPHY = bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C14H15B2BrF4N4
  20. The crystal structure of (E)-3-chloro-2-(2-(2-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  21. Crystal structure of bis(µ2- 4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(µ2-1-(4-pyridyl)piperazine-κ2N:N′)-hexa-aqua-tetra-copper(II), C46H46Cu4I4N10O22
  22. Crystal structure of poly[diaqua-(μ2-2,5-dihydroxyterephthalato-κ2O:O′)(μ2-bis(4-pyridylformyl)piperazine-κ2N:N′)cadmium(II)] dihydrate, C24H28CdN4O12
  23. Crystal structure of poly[aqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(μ3-2,3,5,6-tetrafluoroterephthalato-κ3O:O′:O′′)cadmium(II)], C17H14N4O5F4Cd
  24. Crystal structure of 6-(quinolin-8-yl)benzo[a]phenanthridin-5(6H)-one, C26H16N2O
  25. The crystal structure of aqua-bis(6-chloropicolinato-κ2N,O)copper(II), C12H8Cl2N2O5Cu
  26. Crystal structure of catena-poly[diaqua-bis(μ2-4,4′-bipyridyl-κ2N:N′) disilver(I)] 4-oxidopyridine-3-sulfonate trihydrate, C25H29Ag2N5O9S
  27. The crystal structure of 4-(3-bromophenyl)pyrimidin-2-amine, C10H8BrN3
  28. Crystal structure of 6-oxo-4-phenyl-1-propyl-1,6-dihydropyridine-3-carbonitrile, C15H14N2O
  29. Crystal structure of 4-(2,2-difluoroethyl)-2,4-dimethyl-6-(trifluoromethyl)isoquinoline-1,3(2H,4H)-dione, C14H12F5NO2
  30. Crystal structure of dibromido-(1-methyl-1H-imidazole-κ1N)-(3-(3-methyl-1H-imidazol-3-ium-1-yl)propanoato-κ1O)zinc(II), C11H16Br2N4O2Zn
  31. The crystal structure of 1,1′-(((2 (dimethylamino)ethyl)azanediyl)bis(methylene)) bis(naphthalen-2-olato-κ4 N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)- titanium(IV) ─ dichloromethane (2/1), C33H29N3O6Ti
  32. The layered crystal structure of bis(theophyllinium) hexachloridostannate (IV), C14H18N8O8SnCl6
  33. The crystal structre of 3-(1-ethenyl-1H-imidazol-3-ium-3-yl)propane-1-sulfonate, C8H12N2O3S
  34. Synthesis and crystal structure of di-tert-butyl 1″-acetyl-2,2″,9′-trioxo-4a′,9a′-dihydro-1′H,3′H,9′H-dispiro[indoline-3,2′-xanthene-4′,3″-indoline]-1,3′-dicarboxylate, C39H38N2O9
  35. The crystal structure of 4-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  36. The crystal structure of 1-fluoro-4-(p-tolylethynyl)benzene, C15H11F
  37. The crystal structure of bis[4-bromo-2-(1H-pyrazol-3-yl) phenolato-κ2N,O] copper(II), C18H12Br2CuN4O2
  38. The crystal structure of poly[(μ 3-imidazolato-κ 3 N:N:N′)(tetrahydrofuran- κ 1 O)lithium(I)], C7H11LiN2O
  39. Crystal structure of N′,N′′′-((1E,1′E)-(propane-2,2-diylbis(1H-pyrrole-5,2diyl))bis(methaneylylidene))di(nicotinohydrazide) pentahydrate, C25H24N8O2·5H2O
  40. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-ethyl-1H-imidazol-3-ium hexafluoridophos-phate(V), C9H15F6N2O2P
  41. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(3-thiophenecarboxylato-κ2O,O′)copper(II), C22H14N2O4S2Cu
  42. The crystal structure of 2-amino-3-carboxypyridin-1-ium iodide hemihydrate, C6H8IN2O2.5
  43. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-2-yl)methylene)-tetralone, C18H17NO3
  44. The crystal structure of [μ-hydroxido-bis[(5,5′-dimethyl-2,2′-bipyridine-κ2N,N′)-tricarbonylrhenium(I)] bromide hemihydrate, C30H26N4O9Re2Br
  45. The crystal structure of 2,5-bis(3,5-dimethylphenyl)thiazolo[5,4-d]thiazole, C20H18N2S2
  46. The crystal structure of 5-benzoyl-1-[(E)-(4-fluorobenzylidene)amino]-4-phenylpyrimidin-2(1H)-one, C24H16FN3O2
  47. Crystal structure of monocarbonyl(N-nitroso-N-oxido-phenylamine-κ 2 O,O′)(tricyclohexylphosphine-κP)rhodium(I), C25H39N2O3PRh
  48. Crystal structure of poly[bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N:N′:N″]nickel(II)] hexafluorosilicate, C36H36N12NiSiF6
  49. The crystal structure of 13-(pyrazole-1-yl-4-carbonitrile)-matrine, C19H25N5O
  50. Crystal structure of 3,5-bis((E)-4-methoxy-2-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  51. The crystal structure of N,N′-(Disulfanediyldi-2,1-phenylene)di(6′-methylpyridine)-2-carboxamide, C26H22N4O2S2
  52. Crystal structure of (E)-7-fluoro-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  53. Crystal structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate, C19H16FNO2
  54. The crystal structure of cis-diaqua-bis (N-butyl-N-(pyridin-2-yl)pyridin-2-amine-κ2N,N′)cobalt(II)] dichloride trihydrate, C28H44Cl2N6O5Co
  55. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C18H17NO3
  56. Crystal structure of (E)-2-((3-fluoropyridin-4-yl)methylene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  57. The crystal structure of 6-bromohexanoic acid, C6H11BrO2
  58. The crystal structure of 4-chloro-thiophenol, C6H5ClS
  59. The crystal structure of 4-bromobenzyl chloride, C7H6BrCl
  60. The crystal structure of di-tert-butyl dicarbonate, C10H18O5
  61. The crystal structure of (2-(4-chlorophenyl)-5-methyl-1,3-dioxan-5-yl)methanol, C12H15ClO3
  62. The crystal structure of the co-crystal: 2-hydroxybenzoic acid – N′-(butan-2-ylidene)pyridine-4-carbohydrazide, C10H13N3O·C7H6O3
  63. Crystal structure and anti-inflammatory activity of (E)-7-fluoro-2-((5-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  64. Crystal structure of (E)-7-fluoro-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  65. Crystal structure of 1,1′-(butane-1,4-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C32H56F24N8P4
  66. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2)-cadmium(II), C14H20CdCl2N4O4
  67. Crystal structure of 1-(2-cyanobenzyl)-3-cyano-4-phenyl-4-(2-cyanobenzyl)-1,4-dihydropyridine monohydrate, C56H42N8O
  68. The crystal structure of 3-(carboxymethyl)-1-ethenyl-1H-imidazol-3-ium chloride, C7H9N2O2Cl
  69. The crystal structure of adamantylmethoxydiphenylsilane, C23H28OSi
  70. Redetermination of the crystal structure of (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene, C22H24N4
  71. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H15NO3
  72. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2 N:N′)cobalt(II)] dinitrate, C18H28N10O8Co
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