Startseite Crystal structure of ethyl 2-amino-4-(4-ethoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO6
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Crystal structure of ethyl 2-amino-4-(4-ethoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO6

  • Xue-Kun Liu , Xiao-Yu Geng , Meng Zhang , Bai-Jun Ye , Zhan Shi und Yan-Qiu Wang EMAIL logo
Veröffentlicht/Copyright: 25. Oktober 2018

Abstract

C23H21NO6, triclinic, P1̄ (no. 2), a = 7.624(4) Å, b = 9.197(5) Å, c = 15.058(5) Å, α = 94.13(3)°, β = 102.27(3)°, γ = 106.72(3)°, V = 977.9(8) Å3, Z = 2, Rgt(F) = 0.0662, wRref(F2) = 0.1733, T = 296(2) K.

CCDC no.: 1870692

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

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.26 × 0.21 × 0.17 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.10 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:25.0°, 99%
N(hkl)measured, N(hkl)unique, Rint:4942, 3393, 0.062
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1362
N(param)refined:272
Programs:Bruker [1], Olex2 [2], SHELX [3]
Table 2:

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

AtomxyzUiso*/Ueq
N10.9912(4)0.5063(4)0.15831(19)0.0543(10)
H1A1.0013150.4437690.1974990.065*
H1B1.0764720.5348270.1283000.065*
O10.5419(4)0.4156(3)0.28924(16)0.0515(8)
O20.8004(4)0.3542(3)0.27445(16)0.0587(8)
O30.7496(4)1.0942(3)0.46879(17)0.0579(8)
O40.2531(4)0.6949(3)0.05293(17)0.0606(9)
O50.4254(4)0.8086(3)−0.03804(16)0.0485(8)
O60.8640(4)0.6587(3)0.08029(16)0.0493(8)
C10.3551(7)0.3283(7)0.3920(3)0.0941(18)
H1C0.3411390.2690010.4414090.141*
H1D0.3646930.4323830.4121660.141*
H1E0.2472080.2857180.3410320.141*
C20.5281(7)0.3251(5)0.3633(3)0.0684(14)
H2A0.6382770.3678440.4141940.082*
H2B0.5202450.2204960.3427300.082*
C30.6888(6)0.4256(5)0.2510(2)0.0431(10)
C40.6960(5)0.5281(4)0.1839(2)0.0387(10)
C50.8439(6)0.5586(4)0.1441(2)0.0404(10)
C60.7134(5)0.7055(4)0.0447(2)0.0397(10)
C70.5612(5)0.6823(4)0.0802(2)0.0368(9)
C80.5577(5)0.6184(4)0.1687(2)0.0394(10)
H80.4305130.5492500.1642880.047*
C90.6055(5)0.7481(4)0.2471(2)0.0389(10)
C100.7770(6)0.8588(5)0.2675(2)0.0495(11)
H100.8614480.8542490.2318130.059*
C110.8305(6)0.9780(5)0.3393(2)0.0491(11)
H110.9476041.0527650.3502800.059*
C120.7097(6)0.9852(5)0.3941(2)0.0460(10)
C130.5349(6)0.8766(5)0.3751(3)0.0549(12)
H130.4512020.8816170.4111640.066*
C140.4826(6)0.7585(5)0.3015(2)0.0525(11)
H140.3635950.6858750.2888090.063*
C150.9264(6)1.2121(5)0.4889(3)0.0577(12)
H15A0.9372571.2679600.4370540.069*
H15B1.0289781.1682030.5013670.069*
C160.9358(7)1.3180(5)0.5715(3)0.0788(16)
H16A1.0540971.3989170.5866560.118*
H16B0.8339541.3610380.5584110.118*
H16C0.9253011.2616880.6224620.118*
C170.4040(6)0.7255(5)0.0337(3)0.0453(10)
C180.5867(6)0.8391(4)−0.0707(2)0.0449(10)
C190.7325(5)0.7845(4)−0.0331(2)0.0400(10)
C200.8918(6)0.8182(5)−0.0690(2)0.0512(11)
H200.9921770.783363−0.0440620.061*
C210.9022(7)0.9014(5)−0.1402(3)0.0599(12)
H211.0063820.919831−0.1655330.072*
C220.7566(7)0.9575(5)−0.1740(3)0.0636(13)
H220.7658381.018230−0.2205800.076*
C230.5981(7)0.9261(5)−0.1406(2)0.0556(12)
H230.4995840.963361−0.1650670.067*

Source of material

The title compound was prepared by a reported method. A mixture of 4-hydroxycoumarin (10 mmol), 4-ethoxybenzaldehyde (10 mmol), ethyl cyanoacetate (10 mmol) and 4-(dimethylamino)pyridine (DMAP) (1 mmol) in ethanol (100 mL) was refluxed for 2–3 h and then cooled to room temperature. After filtering the precipitates, they were sequentially washed with ice-cooled water and ethanol and then dried under a vacuum.

Experimental details

H atoms bonded to C and N atoms were positioned geometrically and refined using a riding model, with C—H = 0.93/0.96/0.97/0.98 Å and N—H = 0.86 Å with Uiso(H) = 1.2 times Ueq(C) and 1.2 times Ueq(N).

Comment

Coumarins possess diverse pharmacological and biological activities such [4], [5]. In particular, the antitumor activity of some coumarin compounds has received considerable attention [6].

In the crystal structures of the title compound (Figure), the heterocyclic ring system is both basically planar. The geometric parameters of all moieties in the title structure a comparable with those in related structures [7], [8].

References

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3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Cryst. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

4. Liang, L.; Wang, F. Y.; Shi, J. F.; Hu, Q.; Zhang, L.; Ni, H. B.: One-pot synthesis of 4-arylpolyhydroquinoline derivatives and evaluation of their anti-gastric cancer activity. Lat. Am. J. Pharm. 37 (2018) 80–84.Suche in Google Scholar

5. Medina, F. G.; Marrero, J. G.; Macías-Alonso, M.; González, M. C.; Córdova-Guerrero, I.; Teissier García, A. G.; Osegueda-Robles, S.: Coumarin heterocyclic derivatives: chemical synthesis and biological activity. Nat. Prod. Rep. 32 (2015) 1472–1507.10.1039/C4NP00162ASuche in Google Scholar PubMed

6. Li, J.; Meng, J.; Qu, D.; Zhang, Z.-D.; Li, F.; Yang, X.-H.; Li, J.-T.; Li, M.-K.: New biscoumarin and dihydropyran derivatives as antimicrobials. Res. Chem. Intermed. 41 (2015) 8257–8267.10.1007/s11164-014-1889-xSuche in Google Scholar

7. Wang, J.; Shi, D.-Q.; Wang, X.: Ethyl 9-amino-7-(4-methoxyphenyl)-7H-pyrano[3,2-c]coumarin-8-carboxylate. Acta Crystallogr. E60 (2004) o1401.10.1107/S1600536804017787Suche in Google Scholar

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Received: 2018-06-12
Accepted: 2018-09-30
Published Online: 2018-10-25
Published in Print: 2019-03-26

©2019 Xue-Kun Liu et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of 1H-indole-5-carboxylic acid – 4,4′-bipyridine (2/1), C14H11N2O2
  3. Crystal structure of ethyl 2-amino-4-(4-ethoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO6
  4. Crystal structure of ethyl 2-amino-4-(4-bromothiophen-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C16H16BrNO4S
  5. The crystal structure of 6-amino-2-methyl-8-(4-(methylthio)phenyl)-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile – ethanol (1/1), C20H19N5S
  6. Crystal structure of 6-amino-8-(4-isopropylphenyl)-2-methyl-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile-ethanol (1/1), C24H29N5O
  7. Crystal structure of 1,1′-(ethane-1,2-diyl)bis(3-ethyl-1H-imidazol-3-ium)bis(hexafluorido phosphate), C12H20F12N4P2
  8. Crystal structure of dimethyl (3aS,6R,6aS,7S)-2-pivaloyl-2,3-dihydro-1H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isoquinoline-3a1,6a-dicarboxylate, C21H25NO8
  9. Crystal structure of methyl 4-(4-bromothiophen-2-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H20BrNO3S
  10. Hydrothermal synthesis and crystal structure of catena-poly[bis(4-((pyridin-4-ylmethyl)amino)benzoato-κ3N:O,O′)zinc(II) – 1,2-di(pyridin-4-yl)ethene – water (1/1/1), C38H34N6O5Zn
  11. The crystal structure of 1,2-dimethyl-3,4-dinitrobenzene, C8H8N2O4
  12. Synthesis and crystal structure of trans-tetraaqua-bis(3-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)propanoato-κO)zinc(II) tetrahydrate, C38H48N2O26S2Zn
  13. Crystal structure of diaqua-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-tetrakis(chloropyridin-2-olato-κ1O)-bis(penanthroline-κ2N,N′)diterbium(III), C54H38Cl6Tb2N10O8
  14. Crystal structure of oxidobis(piperidine-1-carbodithioato-κ2S,S′)vanadium(IV), C12H20N2OS4V
  15. Crystal structure of 2-((tert-butyldimethylsilyl)oxy)-5-methylisophthalaldehyde, C15H22O3Si
  16. Crystal structure of catena-poly[tetraiodido-(μ2-1,4-bis(2-methyl-1H-imidazol-1-yl)benzene-κ2N:N′)dimercury(II)], C14H14Hg2I4N4
  17. Crystal structure of tetrakis(n-butyl)-(μ2-1,2-bis(2-oxidobenzoyl)hydrazine-1,2-diido-κ6N,O,O′:N′,O′′,O′′′)ditin(IV), C30H44N2O4Sn2
  18. Crystal structure of ethyl 2-amino-4-(4-hydroxy-3-methoxyphenyl)-7-methyl-5-oxo-4H,5H-pyrano-[4,3-b]pyran-3-carboxylate, C19H19NO7
  19. Crystal structure of 3-aminopyrazine-2-carbohydrazide, C5H7N5O
  20. Crystal structure of ethanol-bis(N-((5-(ethoxycarbonyl)-3,4-dimethyl-1H-pyrrol-2-yl)methylene)benzohydrazonato-κ2N,O)copper(II), C36H42N6O7Cu
  21. Crystal structure of 3-methyl-2-oxo-2H-chromen-7-yl propionate, C13H12O4
  22. Crystal structure of 2-(dimethylamino)ethyl 4-aminobenzoate, C11H16N2O2
  23. Crystal structure of 3-(benzo[d]thiazol-2-ylamino)isobenzofuran-1(3H)-one, C15H10N2O2S
  24. Crystal structure of 3-((1H-benzo[d]imidazol-2-yl)amino)-2-(1H-benzo[d]imidazol-2-yl)isoindolin-1-one, C22H16N6O
  25. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(4-(dimethylamino)phenyldiphenylphosphane-κP)copper(I) tetrafluoroborate, C50H48BCuF4N4P2
  26. Crystal structure of citric acid–acetonitrile (1/1), C8H11NO7
  27. Crystal structure of diethyl 2-(4-methoxyphenyl)-1-phenyl-1,2-dihydropyridine-3,5-dicarboxylate, C24H25NO5
  28. The crystal structure of poly[triaqua-bis(μ3-2,5-dihydroxyterephthalato-κ4O,O′:O′′:O′′′)-(μ4-oxalato-κ4O,O′:O′′,O′′′)cerium(III)], C9H10CeO11
  29. Crystal structure of 1-(5-(anthracen-9-yl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O2
  30. Synthesis and crystal structure of 5-(8-(((2-carboxyethyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate trihydrate, C19H23NO12S
  31. Crystal structure of rac-trans-6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromophenolato-κ4N,N′,O,O′)-bis(methanol)cobalt(III) chloride, C22H25Br2Co8N2O4Cl
  32. Crystal structure of 1-((R)-(2′-(dimethylamino)-[1,1′-binaphthalen]-2-yl))-3-((S)-2-hydroxy-1-phenylethyl)thiourea, C31H29N3OS
  33. Crystal structure and photochemical property of 1,8-bis(p-tolylthio)pyrene, C30H22S2
  34. Crystal structure of 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate, C14H18ClN5O4
  35. Crystal structure of ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate, C11H12N4O2
  36. Crystal structure of trichloro-(4-chloro-2,6-bis(diphenylmethyl)-N-((pyridin-2-yl)methylene)aniline)-aluminum dichloromethane solvate, C39H31AlCl6N2
  37. Bis(ethanol-κO)-bis(6-aminopicolinato-κ2N,O)magnesium(II), C16H22O6N4Mg
  38. Crystal structure of catena-poly[aqua-(μ2-1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ2O:O′)-(1,10-phenanthrolin-κ2N,N′)copper(II)], C16H20B10CuN2O5
  39. Crystal structure of (1,2-dicarba-closo-dodecaborane-1,2-dithiolato κ2S,S′)-bis(1,10-phenanthroline κ2N,N′)zinc(II), C26H26B10Zn4S2
  40. Crystal structure of diaqua-bis(1,10-phenanthroline-κ2N,N′)-bis(1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ3O,O′:O′′) dicobalt(II) — ethanol (1/1), C34H46B20Co2N4O11
  41. Crystal structure of ((5,5′-dimethoxy-2,2′-(1,2-phenylenebis(nitrilomethylidyne)))diphenolato-κ4O,N,O′,N′)copper(II), C22H18N2CuO4
  42. Crystal structure of 1-(5-bromo-2-(4-methoxyphenyl)-1H-indol-7-yl)ethan-1-ol, C17H14BrNO2
  43. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, C34H34N5O2Br
  44. Crystal structure of (Z)-2-((adamantan-1-ylimino)methyl)-5-methoxyphenol, C18H23NO2
  45. Crystal structure of bis((E)-2-ethoxy-6-(((2-hydroxyethyl)imino)methyl)phenolato-κ2N,O)copper(II), C22H28N2CuO6
  46. Crystal structure of 2,3-diphenyl-5,6-bis(4-methoxyphenyl)pyrazine, C30H24N2O2
  47. Crystal structure of dichlorido bis[1-((2,4-dimethyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN]cadmium(II), Cd(C12H13N5)2Cl2
  48. The crystal structure of 1,5-di(naphthalen-2-yl)-3-(pyridin-2-yl)pentane-1,5-dione, C30H23NO2
  49. The crystal structure of 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S
  50. The crystal structure of 1,4-dinitroso-2,3,5,6-tetraacetoxy-piperazine, C12H16N4O10
  51. Crystal structure of bis(2,4,6-trichlorophenyl) malonate, C15H6Cl6O4
  52. The crystal structure of trans-dichlorido-bis(pyridine-2-carboxylato-κ2N,O)platinum(IV), C12H8Cl2N2O4Pt
  53. Crystal structure of 3-nitroquinoline 1-oxide, C9H6N2O3
  54. Crystal structure of 2-(piperidin-1-ium-4-yl)-1H-benzo[d]imidazol-3-ium dichloride dihydrate, C12H21Cl2N3O2
  55. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene, C30H50O
  56. Crystal structure of (E)-4-((2-fluoro-3-(trifluoromethyl)benzylidene)amino)-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C11H8F4N4S
  57. Crystal structure of 5-(4-fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C9H8FN3S
  58. Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n
  59. The crystal structure of 4-(methoxycarbonyl)benzoic acid, C9H8O4
  60. The crystal structure of N,N′-(6-(thiophen-2-yl)-1,3,5-triazine-2,4-diyl)bis(2-methylpropane-2-sulfonamide) – ethyl acetate(2/1), C34H54N10O6S6
  61. Crystal structure of N′-(1-(2-hydroxyphenyl)ethylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide, C18H17N5O2
  62. Crystal structure of 3-(4-methoxyphenyl)-1-phenylprop-2-yn-1-one, C16H12O2
  63. Crystal structure of N′-(1-(benzofuran-2-yl)ethylidene)-2-cyanoacetohydrazide, C13H11N3O2
  64. Crystal structure of hexa-μ2-chlorido-μ4-oxido-tetrakis(1-vinyl-1H-imidazole-κN)tetracopper(II), C20H24Cu4Cl6N8O
  65. Crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide, C22H22O5N2S
  66. Crystal structure of 2-acetyl pyrene, C18H12O
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