Startseite The crystal structure of ethyl 2-amino-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H22N2O6
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The crystal structure of ethyl 2-amino-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H22N2O6

  • Hanbing Song und Hao Li ORCID logo EMAIL logo
Veröffentlicht/Copyright: 16. Oktober 2024

Abstract

C20H22N2O6, triclinic, P 1 (no. 2), a = 5.9101(16) Å, b = 10.619(3) Å, c = 16.466(4) Å, α = 74.619(5)°, β = 82.490(5)°, γ = 82.617(5) %, V = 983.1(5) Å3, Z = 2, R gt(F) = 0.0522, wR ref(F 2) = 0.1536, T = 296(2) K.

CCDC no.: 2388708

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: Yellow 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
θ max, completeness: 25.2°, 99 %
N(hkl)measured, N(hkl)unique, R int: 5,146, 3,514, 0.027
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2,131
N(param)refined: 265
Programs: Bruker, 1 Olex2, 2 SHELX 3 , 4
Table 2:

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

Atom x y z U iso*/U eq
C1 0.8844 (4) 0.1081 (2) 0.81131 (13) 0.0483 (6)
C2 0.6909 (4) 0.1710 (2) 0.84062 (13) 0.0479 (6)
C3 0.6465 (5) 0.1600 (2) 0.92973 (15) 0.0608 (7)
C4 0.3848 (6) 0.2245 (3) 1.03631 (16) 0.0936 (11)
H4A 0.507098 0.251691 1.059762 0.112*
H4B 0.357182 0.135883 1.068011 0.112*
C5 0.1784 (7) 0.3125 (4) 1.0422 (2) 0.1410 (19)
H5A 0.207477 0.399930 1.010920 0.212*
H5B 0.132641 0.311395 1.100545 0.212*
H5C 0.058114 0.284516 1.019225 0.212*
C6 0.5271 (4) 0.2564 (2) 0.78153 (13) 0.0436 (6)
H6 0.370899 0.235097 0.804111 0.052*
C7 0.5778 (3) 0.22779 (19) 0.69623 (13) 0.0415 (5)
C8 0.7729 (4) 0.16253 (19) 0.67389 (13) 0.0419 (5)
C9 0.8430 (4) 0.1372 (2) 0.58979 (13) 0.0517 (6)
H9A 0.819030 0.047381 0.592566 0.062*
H9B 1.005674 0.146094 0.575573 0.062*
C10 0.7141 (4) 0.2281 (2) 0.52066 (14) 0.0533 (6)
C11 0.4647 (4) 0.2388 (3) 0.55227 (16) 0.0673 (8)
H11A 0.383566 0.303986 0.509944 0.081*
H11B 0.406018 0.155312 0.558059 0.081*
C12 0.4113 (4) 0.2752 (2) 0.63501 (14) 0.0492 (6)
C13 0.7546 (5) 0.1786 (3) 0.44148 (17) 0.0877 (10)
H13A 0.916354 0.167901 0.424846 0.132*
H13B 0.680403 0.240722 0.396801 0.132*
H13C 0.692883 0.095685 0.452486 0.132*
C14 0.8010 (5) 0.3647 (3) 0.49890 (18) 0.0796 (9)
H14A 0.778497 0.397962 0.548488 0.119*
H14B 0.717321 0.423114 0.455333 0.119*
H14C 0.961276 0.358332 0.479302 0.119*
C15 0.5390 (4) 0.4008 (2) 0.77267 (12) 0.0410 (5)
C16 0.7375 (4) 0.4579 (2) 0.73913 (14) 0.0506 (6)
H16 0.865120 0.406393 0.722265 0.061*
C17 0.7525 (4) 0.5889 (2) 0.72983 (15) 0.0587 (7)
H17 0.888037 0.626453 0.707177 0.070*
C18 0.5623 (5) 0.6629 (2) 0.75484 (14) 0.0533 (6)
C19 0.3620 (4) 0.6103 (2) 0.78824 (15) 0.0594 (7)
H19 0.234708 0.662382 0.804735 0.071*
C20 0.3516 (4) 0.4798 (2) 0.79707 (14) 0.0532 (6)
H20 0.215570 0.442974 0.819990 0.064*
N1 1.0508 (4) 0.0369 (2) 0.85494 (16) 0.0681 (7)
H1A 1.023 (5) 0.026 (3) 0.9156 (18) 0.093 (10)*
H1B 1.143 (5) 0.003 (3) 0.8274 (17) 0.075 (10)*
N2 0.5749 (5) 0.8027 (2) 0.74494 (14) 0.0748 (7)
O1 0.9358 (2) 0.10961 (14) 0.72781 (9) 0.0499 (4)
O2 0.2328 (3) 0.33832 (17) 0.65114 (10) 0.0616 (5)
O3 0.7662 (3) 0.0980 (2) 0.98416 (10) 0.0848 (7)
O4 0.4489 (3) 0.22822 (17) 0.94891 (9) 0.0694 (6)
O5 0.7604 (5) 0.8446 (2) 0.72364 (19) 0.1305 (11)
O6 0.4020 (4) 0.8695 (2) 0.75925 (15) 0.1112 (9)

1 Source of materials

The synthesis of ethyl 2-amino-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate adopts the following method by a three-component reaction: 4-nitrobenzaldehyde (10 mmol), ethyl 2-cyanoacetate (10 mmol), and cyclohexane-1,3-dione (10 mmol) were mixed in a 100 mL ethanol solution, then DMAP (1 mmol) used as the catalyst was added and stirred. The mixture was heated at 353 K for 6 h and cooled naturally. The precipitate was filtered and recrystallized from an ethanol solution to give yellow crystals of the goal product, yield 62.5 % (based on 4-nitrobenzaldehyde).

2 Experimental details

The structure was solved by Direct Methods with the SHELXL-2014 program. All H-atoms from C atoms were positioned with idealized geometry and refined isotropically (U iso(H) = 1.2U eq(C) or U eq(N)) using a riding model with C–H = 0.930, 0.960, 0.970 and 0.980 Å, respectively. The H-atoms from N atoms were positioned with Q peaks and refined freely with N–H = 0.955 and 0.785 Å.

3 Comment

To date, many single crystal structures of ethyl 2-amino-(4-phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-1-benzopyran-3-carboxylate 5 , 6 and their derivatives have been studied anywhere because of their pharmacological activities, such as 3-cyanophenyl, 7 3-fluorophenyl, 8 3,4-dimethylphenyl, 9 3,5-difluorophenyl, 10 4-fluorophenyl, 11 , 12 , 13 , 14 4-[4-(methanesulfonyl)phenyl], 15 and 4-methylphenyl. 16

The title compound crystallizes in triclinic system, P 1 group (no. 2) with its fomula of C20H22N2O6. The 4-nitrophenyl group is almost coplanar due to the rigidity of benzene ring, and the 4-hydropyran ring is twisted from planarity. A dimer is generated by the hydrogen bond N1–H1A⋯O3, then was linked with hydrogen bonds N1–H1B⋯O6, C9–H1A⋯O5, C16–H16⋯O2, and C14–H14B⋯O2 to form one 3D supramolecular structure. All the bond lengths are similar to the reported results mentioned above. 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16


Corresponding author: Hao Li, Department of Medical Oncology, Xuzhou Central Hospital, Xuzhou, 221009, Jiangsu, P.R. 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: None declared.

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

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Received: 2024-08-22
Accepted: 2024-10-04
Published Online: 2024-10-16
Published in Print: 2024-12-17

© 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. Crystal structure of 3-nitrophenol-2,1,3-benzoselenadiazole (1/1), C12H9N3O3Se
  4. Crystal structure of diaqua-(hydroxido)-{μ-[2-(hydroxy)-5-[(4-nitrophenyl)diazenyl]benzoato]}-{2-hydroxy-5-[(4-nitrophenyl)diazenyl]benzoato}-(1,10-phenanthroline)-diterbium hydrate, C38H27.4N8O12.2Tb
  5. Crystal structure of poly[bis(μ3-3-fluoro-4-(1H-1,2,4-triazol-1-yl)benzoato-κ3 O:O′:N)cadmium(II)] – dimethylformamide (1/1), C21H17CdF2N7O5
  6. The crystal structure of 2-amino-N-(pyridin-2-yl)benzamide, C12H11N3O
  7. The crystal structure of 2,3-di(pyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one, C18H14N4O
  8. Crystal structure of 2-chloro-4-fluorobenzyl (R)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18ClFO3
  9. Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid]-(methylsulfinyl)methane, C15H16N2O6S
  10. The crystal structure of 2-ethyl-1,1-dimethyl-1H-benzo[e]indole, C16H17N
  11. The crystal structure of (Z)-5-amino-N -hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  12. The crystal structure of 2,2,5-trimethyl-3-(4-(4-(5-phenyl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)phenyl)imidazolidin-4-one, C24H24N4O2S
  13. The crystal structure of tetrakis(μ2-acetato-κ2 O:O′)-bis[(4′-phenyl-4,2′:6′,4″-terpyridine-κ1 N)dicopper(II)], C25H21CuN3O4
  14. Crystal structure of poly(3-thiophenecarboxylato-κ 3 O,O′:O′)-(methanol-κO)cadmium(II), C11H10O5S2Cd
  15. The crystal structure of dichloridobis[4′-(p-methoxylphenyl)-4,2′:6′,4″-terpyridine-κN] zinc(II), C44H34Cl2N6O2Zn
  16. The crystal structure of 1-(2-carboxyethyl)-1H-imidazole 3-oxide
  17. Crystal structure of 1,1′,1″-(nitrilotris(ethane-2,1-diyl))tris(3-(4-(((E)-pyridin-2-ylmethylene)amino)phenyl)urea), C45H47N13O4
  18. Crystal structure of a (E)-4-bromo-N-(4-(diethylamino)-2-hydroxybenzylidene) benzenaminium acetate ─ 4-bromoaniline (1/1)
  19. Crystal structure of 2,2′-(iminobis(methylene))bis(benzimidazolium) bis(p-toluenesulfonate), C30H31N5O6S2
  20. The crystal structure of alogliptinium meta-chlorobenzoate
  21. Crystal structure of 4-bromobenzyl 2-(6-methoxy-naphthalen-2-yl)propanoate, C21H19BrO3
  22. The hydrated double salt structure of (E)-4-(2-benzylidenehydrazine-1-carbonyl)pyridin-1-ium cation with 2-hydroxybenzoate and benzoate anions
  23. Crystal structure of (R)(R)-5-chloro-3-((S,1E,3E)-3,5-dimethyl-hepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-2,6,7,8-tetrahydroisoquinolin-7-yl acetate, C21H24ClNO4
  24. The crystal structure of bis(3-oxo-1,3-diphenylprop-1-en-1-olato-κ 2 O:O′)-bis(1,4-dioxane-κ 1 O)nickel(II), C38H38O8Ni
  25. Crystal structure of poly[aqua-(pyridine-3-carboxylato-κ1 N)(pyridine-3-carboxylato-κ2 O,O′) cadmium(II)] dihydrate, C12H14N2O7Cd
  26. The crystal structure of 4-(4-phenyl-5-(((1-(2,4,6-tribromophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-4H-1,2,4-triazol-3-yl)pyridine, C22H14Br3N7S
  27. The crystal structure of N-benzylquinoline-2-carbothioamide, C17H14N2S
  28. Crystal structure of bis(3-isopropylphenyl)-4,4′-bipyridinium dichloride dihydrate, C28H30N2⋅2Cl⋅2H2O
  29. The crystal structure of ethyl 2-amino-4-(cyanophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C19H18N2O4
  30. Crystal structure of (4R,10S)-6-hydroxy-7-isopropyl-4,10-dimethyl-1,2,3,5-hexahydro-6,10-epoxyazulen-9-one, C15H22O3
  31. The crystal structure of (E)-(2-(2-hydroxy-3-methoxybenzylidene)aminophenyl)arsonic acid, C14H14AsNO5
  32. The crystal structure of poly[(μ 2-2-aminoisophthalato-κ4O,O′:O″:O″′)-(N-methylpyrrolidone κ1O)-dioxido-uranium(VI)], C13H14N2O7U
  33. The crystal structure of the co-crystal isonicotinamide · terephthalic acid, C8H6O4·2(C6H6N2O)
  34. The crystal structure of (E)-1-phenyl-3-(p-tolylthio)but-2-en-1-one, C17H16OS
  35. The crystal structure of 4,5-bis((Z)-chloro(hydroxyimino)methyl)-1H-imidazol-3-ium chloride monohydrate
  36. The crystal structure of 1,2-bis(4-(dimethylamino)phenyl)ethane-1,2-dione. C18H20N2O2
  37. Crystal structure of 2-chloro-4-fluorobenzyl 2-acetoxybenzoate, C16H12ClFO4
  38. Crystal structure of methyl 1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate, C19H14N2O2
  39. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl)(5-fluoro-2-iodophenyl)methanone, C19H17FINO4
  40. Crystal structure of tetrachlorido-bis(1-[(1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2 N:N′)dicopper, C36H32Cu2N24Cl4
  41. Crystal structure of 2-(2,3-bis(4-methoxyphenyl)-1H-pyrrolo[2,3-b]quinoxalin-1-yl)anilin, C30H24N4O2
  42. Crystal structure of 5,7-dihydroxy-2-phenyl-4H-chromen-4-one–N,N-dimethylformamide(1/1), C18H17NO5
  43. The crystal structure of bis(μ 2-biphenyl-2,2′-dicarboxylato)-diaqua-bis(nitrato)-bis(2,2′:6′,2′′-terpyridine)dineodymium(III), C46H32I2N8Nd2O16
  44. Crystal structure of (Z)-4-amino-N -((4-chlorophenyl)(phenyl)methylene)benzohydrazide, C20H16ClN3O
  45. Crystal structure of (E)-6,8-dimethoxy-4-(4-morpholinobenzylidene)-3,4-dihydro-1-benzoxepin-5(2H)-one, C23H25NO5
  46. Crystal structure of (R)-2-((3-(3-aminopiperidin-1-yl)-6-methyl-5-oxo-1,2,4-triazin-4(5H)-yl) methyl)-4-fluorobenzonitrile benzoate monohydrate, C24H27FN6O4
  47. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylato-κ 3 N,O,O)copper(II)]monohydrate, C12H15NO9Cu
  48. Crystal structure of (((4-chlorophenyl)sulfonyl)glycinato-κ 2 N,O)bis(1,10-phenanthroline-κ 2 N,N′)cobalt(II) tetrahydrate, C32H30ClCoN5O8S
  49. Crystal structure of (((3-nitrophenyl)sulfonyl)-β-alaninato-κO)bis(2,2′-bipyridine-κ 2 N, N′)copper(II) 3-nitrobenzenesulfonate, C35H29CuN7O11S2
  50. Crystal structure of 3-phenoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C27H24O4
  51. 6-(2′,3′-Dihydroxy-3′-methylbutyl)-7-methoxy-8-(3″-methylbut-2″-en-1″-yl)-2H-chromen-2-one, C20H26O5
  52. Crystal structure of bromido-(2,2′:6′,2″-terpyridine-4′-onato-κ3N)palladium(II) methanol solvate
  53. The crystal structure of ethyl 2-amino-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H22N2O6
  54. Crystal structure of (1E,3E,5E)-1,6-bis(4-(pentyloxy)phenyl)hexa-1,3,5-triene, C28H36O2
  55. The crystal structure of tris(2-bromo-4-methylphenyl)amine, C21H18Br3N
  56. The crystal structure of 3-(2,5-dimethylanilino)-1-(2,5-dimethylphenyl)-4-methyl-1H-pyrrole-2,5-dione, C21H22N2O2
  57. Crystal structure of dicarbonyl (μ2-indole-2-carboxylato κ2 O:O′)tris(triphenylarsine-κAs)dirhodium(I) acetone solvate, C68H56As3NO5Rh2
  58. The crystal structure of 4-chloro-2-formylphenyl 4-methylbenzenesulfonate, C14H11ClO4S
  59. Crystal structure of 4-iodobenzyl 2-(6-methoxynaphthalen-2-yl) propanoate, C21H19IO3
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