Home Crystal structure of 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester, C17H13F4NO4
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Crystal structure of 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester, C17H13F4NO4

  • Zheng-Bao Qi , Man-Jing Zhu ORCID logo EMAIL logo , Xu-Liang Nie ORCID logo , Guo-Ping Huang and Jian-Ping Huang ORCID logo EMAIL logo
Published/Copyright: December 14, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 1

Abstract

C17H13F4NO4, monoclinic, P21/n (no. 14), a = 5.470(4) Å, b = 26.141(17) Å, c = 11.689(8) Å, β = 90.01°, V = 1671.3(19) Å3, Z = 4, R gt (F) = 0.0612, w R ref (F2) = 0.1650, T = 296(2) K.

CCDC no.: 2309925

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: 0.23 × 0.15 × 0.12 mm
Wavelength:

μ:		 Mo Kα radiation (0.71073 Å)

0.13 mm−1
Diffractometer, scan mode:

θmax, completeness:		 Bruker APEX-II, φ and ω

25.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 12318, 3110, 0.038
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2003
N(param)refined: 236
Programs: Bruker [1], SHELX [2, 3], Diamond [4]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.4256 (7) 0.10776 (13) 0.1482 (3) 0.0640 (9)
C2 0.2953 (8) 0.06564 (14) 0.1825 (4) 0.0774 (11)
C3 0.0946 (8) 0.07244 (17) 0.2500 (4) 0.0809 (11)
C4 0.0326 (7) 0.12043 (17) 0.2814 (3) 0.0708 (10)
C5 0.1619 (6) 0.16284 (14) 0.2500 (3) 0.0605 (9)
H5 0.1158 0.1951 0.2757 0.073*
C6 0.3622 (6) 0.15700 (12) 0.1794 (2) 0.0525 (8)
C7 0.5149 (6) 0.20285 (11) 0.1511 (2) 0.0526 (8)
C8 0.5884 (6) 0.21432 (11) 0.0353 (2) 0.0488 (7)
C9 0.4732 (6) 0.19397 (12) −0.0691 (3) 0.0539 (8)
C10 0.1507 (8) 0.14148 (17) −0.1463 (3) 0.0848 (12)
H10A 0.0057 0.1607 −0.1673 0.102*
H10B 0.2596 0.1408 −0.2117 0.102*
C11 0.0838 (13) 0.0905 (2) −0.1161 (4) 0.143 (2)
H11A 0.2276 0.0695 −0.1128 0.215*
H11B −0.0264 0.0771 −0.1725 0.215*
H11C 0.0050 0.0907 −0.0427 0.215*
C12 0.7787 (6) 0.24847 (11) 0.0165 (3) 0.0527 (8)
H12 0.8230 0.2534 −0.0595 0.063*
C13 1.0980 (6) 0.31036 (13) 0.0625 (3) 0.0636 (9)
H13A 1.1491 0.3042 −0.0157 0.076*
H13B 1.2378 0.3045 0.1119 0.076*
C14 1.0188 (6) 0.36375 (13) 0.0739 (3) 0.0577 (8)
C15 1.1403 (9) 0.40227 (17) 0.1157 (4) 0.1003 (15)
H15 1.2973 0.4017 0.1462 0.120*
C16 0.9833 (15) 0.44570 (19) 0.1051 (5) 0.132 (2)
H16 1.0164 0.4784 0.1322 0.158*
C17 0.7904 (13) 0.43205 (19) 0.0524 (5) 0.1170 (19)
H17 0.6623 0.4536 0.0318 0.140*
F1 0.6232 (4) 0.09953 (8) 0.0822 (2) 0.0898 (7)
F2 0.3637 (6) 0.01847 (9) 0.1490 (3) 0.1212 (10)
F3 −0.0329 (6) 0.03107 (11) 0.2835 (3) 0.1268 (11)
F4 −0.1667 (5) 0.12543 (11) 0.3494 (2) 0.1085 (9)
N1 0.9043 (5) 0.27469 (9) 0.0925 (2) 0.0562 (7)
H1 0.8700 0.2705 0.1637 0.067*
O1 0.5822 (5) 0.22975 (9) 0.23312 (18) 0.0718 (7)
O2 0.5445 (5) 0.20273 (10) −0.16518 (19) 0.0744 (7)
O3 0.2722 (5) 0.16653 (10) −0.05031 (19) 0.0758 (7)
O4 0.8016 (6) 0.37999 (12) 0.0304 (3) 0.1080 (11)

1 Source of materials

To a stirred solution of 3-dimethylamino-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester (31.9 g, 0.1 mol) in CH2Cl2 (150 mL) was added α-furan-2-yl-methylamine (1.0 g, 0.1 mol), and then the reaction mixture was refluxed for about 0.5 h. After the reaction completed (monitored by TLC), the CH2Cl2 was distillated under reduced pressure to give crude product. The crude product was poured into water (40 mL) and extracted with EtOAc (50 mL × 3). The EtOAc solvent was evaporated to provide 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester being suitable for X-ray analysis in 85.0 % yield. 1H (400 MHz) and 13C (100 MHz) NMR spectra of 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester were recorded on a Bruker Avance 400 spectrometer in CDCl3 using tetramethylsilane (TMS) and CDCl3 (13C, δ 77.0 ppm) as internal standards. J-values were given in Hertz. 1H NMR (400 MHz, CDCl3): δ = 1.09–1.13 (t, J = 8.0, 3H, OCH2CH3), 4.05–4.10 (q, J = 8.0, 12.0 Hz, 2H, OCH2CH3), 4.57–4.59 (d, J = 8.0 Hz, 2H, NHCH2), 6.34–6.39 (m, 2H, Furanyl-H), 6.95–7.01 (m, 1H, Ph–H), 7.45–7.47 (d, J = 8.0 Hz, 1H, OCH=C), 8.18–8.21 (d, J = 12.0 Hz, 1H, C=CHNH), 10.98 (br, 1H, NH) ppm. 13C NMR (100 MHz, CDCl3): δ = 187.14, 166.25, 160.56, 160.11, 148.29, 143.69, 143.58, 143.50, 110.72, 109.98, 109.79, 109.29, 109.09, 101.62, 60.06, 46.50, 14.00 ppm.

2 Experimental details

All H atoms were included in calculated positions and refined as riding atoms, with C–H = 0.90–0.97 Å with Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for all other H atoms.

3 Comment

Quinolones have been popularized rapidly in clinic and become significant drug in the development, production and application all over the world due to wider antibacterial spectrum and stronger antibacterial activity than common antibiotics [5, 6]. After being used or even abused for a long time, quinolones have been seriously resisted by bacteria because of gene mutations and also have the inevitable side effects [7], [8], [9]. Nowadays, a new effective fluoroquinolones against bacteria drug-resistant and side effects have been researched and developed [10–13]. Recently, an impactful and high-yielding method for the synthesis of fluoroquinolones is developed in our group, and single crystals of several key intermediates are achieved.

In the molecule of the title compound bond lengths and angles within 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester are very similar to those given in the literature [11, 12]. The dihedral angles between the C1–C6 benzene ring, O2–C9–O3 carboxyl group and the furan ring are 61.0 ( 1 ) ∘ , 66.2 ( 3 ) ∘ and 86.3 ( 3 ) ∘ . The torsion angles of C5–C6–C7–C8, C6–C7–C8–C9, C6–C7–C8–C12, C7–C8–C12–N1, C8–C12–N1–C13, C12–N1–C13–C14 and N1–C13–C14–C15 are − 132.6 ( 3 ) ∘ , 18.9 ( 5 ) ∘ , − 163.1 ( 3 ) ∘ , − 2.5 ( 5 ) ∘ , − 178.7 ( 3 ) ∘ , 104.7 ( 4 ) ∘ , and 138.6 ( 4 ) ∘ , respectively. Intermolecular N–H⋯O hydrogen bonds between nitrogen atom (N1) of amino group and oxygen atoms (O2) of carboxyl group connect the adjacent title compound to form a one dimensional chain.

Corresponding authors: Man-Jing Zhu, Academic Affairs Office, Jiangxi Open University, Nanchang 330046, People's Republic of China, E-mail: ; and Jian-Ping Huang, Key Laboratory of Chemical Utilization of Plant Resources of Nanchang, College of Chemistry and Materials, Jiangxi Agricultural University, Nanchang 330045, People’s Republic of China; and Nanchang Jiangteng Pharmaceutical Ltd, Nanchang 330045, People’s Republic of China, E-mail:

Acknowledgments

X-ray data were collected at Instrumental Analysis Center Nanchang Hangkong University, Nanchang, 330063, People’s Republic of China.

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

  2. Research funding: This study was supported by grants from Natural Science Foundation of Science and Technology Department of Jiangxi Province (No. 20151BBF60081; 20171BBE50027; 20171BBG70029; 20202BBEL53028), Science and Technology Research Project of Education Department of Jiangxi Province (No. GJJ170275, GJJ2210601), Natural Science Foundation of Nanchang City (No. 2014HZZC07; 2018CXTD014), Natural Science Foundation of Fuzhou City, Jiangxi Province (No.202205127297), Natural Science Foundation of Jiangxi Agriculture University (No. 09004634; 09005194; 201610410007; 201610410079), and 2021 Innovation Team Project of Ji’an City, Jiangxi Province.

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

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Received: 2023-10-27
Accepted: 2023-11-23
Published Online: 2023-12-14
Published in Print: 2024-02-26

© 2023 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  2. New Crystal Structures
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  4. Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
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  13. The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
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https://doi.org/10.1515/ncrs-2023-0467
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of poly[diaqua-(μ4-3,3′-di(1H-1,2,4-triazol-1-yl)-[1,1′-biphenyl]-4,4′-dicarboxylate-N:N′:O:O′)cadmium(II)], C18H14N6O6Cd
  4. Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
  5. The crystal structure of 8-methoxy-2,2-diphenyl-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C29H25BN2O3S
  6. Crystal structure of aqua-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)copper(II) 5-carboxyisophthalate tetrahydrate, C25H50N4CuO11
  7. The crystal structure of 1-(naphthalen-2-ylsulfonyl)-2,2-diphenyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinoline, C31H23BN2O2S
  8. Crystal structure of iodido-(η6-benzene) (1-(pyridin-2-yl)-N-(p-fluoro-methanamine)-κ2N,Nʹ)ruthenium(II) hexaflourophosphate, (C18H15F7IN2RuP)
  9. The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2
  10. Crystal structure of tricyclohexyl[4-(4H-1,2,4-triazol-4-yl)-benzoato-κO]tin(IV), C27H39N3O2Sn
  11. Crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)cadmium(II)]monohydrate, C12H15NO9Cd
  12. Crystal structure of ethyl 2-((4-(3,5-dimethylisoxazol-4-yl)-2,6-difluorophenyl)amino)benzoate, C20H18F2N2O3
  13. The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
  14. The crystal structure of 1,2-bis(2,4-dinitrophenyl) hydrazine, C12H8N6O8
  15. Crystal structure of 1-(2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one, C19H14Cl2N2O3
  16. The crystal structure of 5-amino-5-oxo-4-(1-oxo-4-(2-oxopyrrolidin-1-yl)isoindolin-2-yl)pentanoic acid, C17H19N3O5
  17. Crystal structure of N2,N6-bis(2-(((Z)-5-bromo-2-hydroxybenzylidene)amino) phenyl)pyridine-2,6-dicarboxamide, C33H23Br2N5O4
  18. The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
  19. The crystal structure of 3-((tert-butyldiphenylsilyl)methyl)-5,5-diphenyl-6-(p-tolyl) tetrahydro-2H-pyran-2-one, C41H42O2Si
  20. Crystal structure of 9-fluoro-4-(6-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  21. The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3
  22. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-isopropyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C10H14F6N2P
  23. The crystal structure of 2,2-di(thiophen-3-yl)-1-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C24H19BN2O2S3
  24. Crystal structure of 5-bromo-1-(2-iodobenzoyl)-1H-indole-3-carbaldehyde, C16H9BrINO2
  25. The crystal structure of monocarbonyl-2-carboxypyridinato-κ2N,O-triphenylphosphine-rhodium(I) acetonitrile solvate, C26H20.50N1.50O3PRh
  26. Crystal structure of dichlorido-tetrakis(1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1N)manganese(II), C60H68O4N12Cl10Mn
  27. Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi
  28. Crystal structure of langite from Mine du Pradet (France)
  29. The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S
  30. Synthesis and crystal structure of bis{2-(((4-acetophenone)imino)methyl)-4-fluorophenolato-κ2N,O}zinc(II), C30H22F2N2O4Zn
  31. The crystal structure of poly[(tripyridine-κ3N,N′,N″) μ3-(pyridine-3,4-dicarboxylate-κ3N:O:O′) manganese(II)], C22H22N4O8Mn
  32. The crystal structure of (E)-4-chloro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15ClN2O2
  33. Synthesis and crystal structure of bis{2-(tert-butyl)-6-((E)-((4-((E)-1-(methoxyimino) ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II), C40H46CoN4O4
  34. Crystal structure of tetraaqua-[(1-(carboxymethyl)-1H-pyrazole-3-carboxylato-κ2N,O)cobalt(II)], C6H12CoN2O8
  35. (6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3′,4′]cycloocta [1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol, C22H26O6
  36. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)benzoic acid, C18H14Cl2N2O3
  37. Crystal structure of (5aS,6aS,8aR,9R,11aS, 11bS,13R,13aS)-1,1,8a,11a-tetramethyl-9-((S)-1-((S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3-oxo-1,7,8,8a,9,10,11,11a,11b,12,13,13a-dodecahydro-3H,6H-cyclopenta[5,6]cyclopropa[1,8a]naphtho[2,1-c]oxepin-13-yl acetate, C32H44O6
  38. Crystal structure of catena-poly[triaqua-(μ2-1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-O,O′:O″)cobalt(II)], C12H12N2O8Co
  39. Crystal structure of 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester, C17H13F4NO4
  40. Crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3-methoxybenzoate, C13H16O6
  41. Crystal structure of 4-bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, C13H7BrClF3N2
  42. The crystal structure of triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ3N,O,O)nickel(II) monohydrate, C12H15NO9Ni
  43. Crystal structure of dihydroxy(2,4,6-triisopro-pylphenyl)telluronium trifluoromethanesulfonate, C16H25F3O5STe
  44. The crystal structure of 1-(carboxymethyl)-1H-imidazole 3-oxide
  45. The crystal structure of 1,3,5-tris(dibromomethyl)benzene, C9H6Br6
  46. Crystal structure of (Z)-3-(4-methoxyphenyl)-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-N-phenylthiazol-2(3H)-imine, C25H21N5OS
  47. Crystal structure of (Z)-3-(3-(4-hydroxyphenyl)-2-(phenylimino)-2,3-dihydrothiazol-4-yl)-2H-chromen-2-one, C24H16N2O3S
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