Home The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
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The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7

  • Bimal Bhushan Chakraborty , Saurav Paul , Siddique Anwar and Sudip Choudhury ORCID logo EMAIL logo
Published/Copyright: September 22, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 6

Abstract

C23H19NO7, monoclinic, P21/n (no. 14), a = 17.9964(9) Å, b = 5.9211 Å, c = 18.8608(10) Å, β = 98.201(3)°, V = 1989.23(18) Å3, Z = 4, R gt (F) = 0.0496, wR ref (F2) = 0.1561, T = 296 K.

CCDC no.: 2290513

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: White block
Size: 0.34 × 0.31 × 0.31 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.11 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 30.2°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 39,088, 5852, 0.031
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 4321
N(param)refined: 283
Programs: Bruker [1], WinGX/ORTEP [2], Olex2 [3], SHELX [4, 5]
Table 2:

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

Atom x y z Uiso*/Ueq
O1 −0.06233 (6) 0.77070 (19) 0.79398 (5) 0.0446 (3)
O2 −0.16815 (7) 0.7565 (2) 0.71989 (7) 0.0631 (3)
O3 0.09556 (6) 0.07707 (19) 1.03857 (5) 0.0452 (3)
O4 0.23410 (6) −0.02443 (19) 1.11960 (6) 0.0478 (3)
H11 0.276739 −0.027579 1.141767 0.072*
O5 0.37956 (7) 0.1893 (2) 1.13966 (7) 0.0605 (3)
O6 0.38628 (6) 0.5189 (2) 1.08222 (6) 0.0490 (3)
O7 0.36688 (8) 0.6237 (2) 0.76172 (6) 0.0600 (3)
N1 0.15631 (6) 0.38896 (19) 0.99770 (5) 0.0322 (2)
C1 −0.12908 (8) 0.6654 (3) 0.76924 (8) 0.0456 (3)
C2 −0.14580 (8) 0.4590 (3) 0.80354 (8) 0.0483 (4)
H1 −0.192038 0.389829 0.789989 0.058*
C3 −0.09623 (8) 0.3635 (3) 0.85479 (7) 0.0409 (3)
H2 −0.107979 0.227897 0.875487 0.049*
C4 −0.02511 (7) 0.4699 (2) 0.87775 (6) 0.0318 (3)
C5 0.02996 (7) 0.3747 (2) 0.92912 (6) 0.0317 (3)
H3 0.021171 0.236869 0.950071 0.038*
C6 0.09774 (7) 0.4864 (2) 0.94872 (6) 0.0307 (3)
C7 0.10872 (7) 0.6974 (2) 0.91830 (7) 0.0382 (3)
H4 0.153014 0.775959 0.932891 0.046*
C8 0.05525 (8) 0.7909 (2) 0.86720 (8) 0.0408 (3)
H5 0.063607 0.929947 0.846794 0.049*
C9 −0.01108 (7) 0.6750 (2) 0.84669 (7) 0.0347 (3)
C10 0.15041 (7) 0.1960 (2) 1.03673 (6) 0.0329 (3)
C11 0.22604 (7) 0.1581 (2) 1.07840 (7) 0.0352 (3)
C12 0.27300 (7) 0.3237 (2) 1.06551 (7) 0.0359 (3)
C13 0.23225 (7) 0.4895 (2) 1.01285 (6) 0.0328 (3)
H6 0.228852 0.635266 1.036763 0.039*
C14 0.26917 (7) 0.5240 (2) 0.94608 (7) 0.0332 (3)
C15 0.26335 (8) 0.3651 (2) 0.89143 (7) 0.0389 (3)
H10 0.237041 0.231778 0.895777 0.047*
C16 0.29636 (9) 0.4031 (3) 0.83046 (8) 0.0435 (3)
H9 0.291646 0.296369 0.793922 0.052*
C17 0.33657 (8) 0.6010 (3) 0.82386 (7) 0.0411 (3)
C18 0.34301 (9) 0.7598 (3) 0.87784 (8) 0.0444 (3)
H8 0.369783 0.892380 0.873804 0.053*
C19 0.30902 (8) 0.7195 (3) 0.93845 (7) 0.0408 (3)
H7 0.313268 0.827044 0.974731 0.049*
C20 0.40555 (13) 0.8276 (4) 0.75164 (11) 0.0685 (6)
H12 0.373422 0.953834 0.757207 0.103*
H13 0.419531 0.829603 0.704395 0.103*
H14 0.449839 0.837121 0.786519 0.103*
C21 0.35100 (8) 0.3347 (3) 1.09987 (7) 0.0408 (3)
C22 0.46418 (9) 0.5419 (4) 1.11482 (11) 0.0629 (5)
H15 0.492521 0.408544 1.105390 0.076*
H16 0.467217 0.560120 1.166259 0.076*
C23 0.49490 (12) 0.7444 (5) 1.08274 (18) 0.0979 (9)
H17 0.547761 0.755622 1.099206 0.147*
H18 0.470043 0.877118 1.096781 0.147*
H19 0.486755 0.731402 1.031478 0.147*

1 Source of material

A mixture of 6-amino coumarin (1 eq), anisaldehyde (1 eq), ethylenedicarboxylate (1.3 eq), and iodine (catalytic amount) was dissolved in acetonitrile and refluxed for about 1 h. The progress of the reaction was monitored by TLC. On completion of the reaction, the solvent was removed in vacuo using rotary evaporator. The precipitate obtained was washed with ethanol and then recrystallised from chloroform to get the product in high purity (yield 82 %, m.p. 191–193 °C). White crystals of the title compound were obtained by slow evaporation of solvent from a chloroform solution of the compound at room temperature. IR (KBr, cm−1): 3375 (O–H), 1730 (C=O ester), 1658 (C=O lactam). 1H NMR (400 MHz, CDCl3, δ ppm): 1.12 (t, 7.2 Hz, 3H), 3.66 (s, 3H), 4.12 (q, 2H), 5.61 (s, 1H), 6.31 (d, J = 9.6, 1H), 6.70 (d, J = 6.8, 2H), 7.06 (d, J = 8.8, 2H), 7.15 (d, 1H, J = 8.8), 7.40 (dd, J = 9.2, 2.4, 1H), 7.52 (d, J = 9.6, 1H), 7.70 (d, J = 2.4, 1H), 9.01(broad, 1H). 13C NMR (100 MHz, CDCl3, δ ppm): 13.9, 55.2, 61.2, 61.4, 113.5, 114.2, 117.3, 119, 121.3, 125.2, 126.1, 128.5, 132.8, 143, 151.3, 156.1, 159.8, 160.2, 162.8, 165. Anal. Calc. for C23H19NO7: C 65.56; H 4.54; N 3.32; O 26.58. Found: C 65.49, H 4.51, N 3.28 %.

All chemicals used were purchased from Sigma Aldrich and used as received without further purification.

2 Experimental details

The structure was solved by Direct Methods and refined against F2 by a full-matrix least-squares procedure using Shelxl program [4] under Olex2 suite [3]. Systematically absent reflections were automatically rejected. Two small angle reflections affected by the beamstop were omitted during refinement. H atoms were included in calculated positions and refined as riding atoms, with C–H = 0.93–0.98 Å with Uiso(H) = 1.5 Ueq(C) for methyl H and hydroxyl H atoms. Uiso(H) was set to 1.2 Ueq(C) for all other H atoms. Me and OH groups were refined as rotating groups.

3 Comment

2–Pyrrolidinones are a class of naturally occurring simple five membered nitrogen containing heterocyclic compounds occupying a special place in synthetic as well as in medicinal chemistry [6, 7]. They have a broad spectrum of significant biological activities that include antimicrobial [8], anticancer [9], HIV-1 integrase inhibitors [10], and many more. In material application, 2-pyrrolidinones have been used as sensitizers in dye sensitised solar cell [11], fluorescence probe for the detection of Cr(VI) metal ion [12], etc.

Single-crystal structure analysis revealed that the title compound crystallized in the monoclinic space group P21/n. The title molecule is shown in the figure. Bond lengths and angles are all in the expected ranges [13, 14]. Obtained C–C bond precision was 0.0020 Å.

Corresponding author: Sudip Choudhury, Department of Chemistry, Centre for Soft Matter, Assam University, Silchar 788011, India, E-mail:

Funding source: NRB, Govt of India (SC)

Acknowledgments

The authors thankfully acknowledge DST–FIST (Chemistry Dept) of Assam University and USIC, Gauhati University, India for recording of the XRay data.

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

  2. Competing interests: The authors declare no conflicts of interest regarding this article.

  3. Research funding: This work was partially supported by the NRB, Govt of India (SC). DSt–INSPIRE Fellowships to SP and UGC Fellowship to BBC are acknowledged.

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Received: 2023-07-29
Accepted: 2023-08-24
Published Online: 2023-09-22
Published in Print: 2023-12-15

© 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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  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H52FNO3
https://doi.org/10.1515/ncrs-2023-0350
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of bis(dimethylammonium) poly[(μ4-1,1′-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato))-κ6O1, N2:O2:O3:O1′,N2′]nickel (II)], C22H26N6NiO8
  4. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-((pyridin-4-ylmethyl)amino)benzoato-κ2N:O)cobalt(II)] – 4,4′-bipyridine – water (1/2/2)
  5. Crystal structure of (2S,3S,4S,5S, Z)-2,3,5,6-tetrakis(benzyloxy)-4-hydroxyhexanal oxime, C34H37NO6
  6. The crystal structure of hexakis(3-thiophenecarboxylato-κ2O,O″)-bis(1,10-phenanthroline-κ2N,N′) trimanganese(II), C54H34N4O12S6Mn3
  7. Crystal structure of catena-poly[(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(4-bromobenzoate-κ2O:O′)-(μ-2-bromobenzoate-κ2O,O′)nickel(II)] – water (2/1), C30H21Br2N2NiO4.5
  8. The crystal structure of poly[(μ3-1,3-phenylenedioxydiacetate-κ5O,O,O′,O″,O‴)-bis(4′-(4-(1H-imidazol-1-yl)phenyl)-4,2′:6′,4″-terpyridine-kN) cadmium(II)], C58H42CdN10O6
  9. The crystal structure of 5-chloro-6′-methyl-3-(4-(methylsulfonyl)phenyl)-[2,3′-bipyridin]-1′-ium 4-methylbenzenesulfonate
  10. Crystal structure of poly[(μ-benzoato)-(μ-cis-4–hydroxy-D-proline)lithium], C12H14LiNO5
  11. The crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O′)-copper(II)] monohydrate, C7H6NO6ICu
  12. The crystal structure of catena-[diaqua-(4-acetylphenoxyacetato-κ2O,O)-bis(4-acetylphenoxyacetato-κ3O,O:O)-dihydrate-lanthanum(III)]–4,4′-bipyridine (2/1), C35H35NO14La
  13. The crystal structure of catena-poly[(4-iodopyridine-2,6-dicarboxylato-κ4 O,N,O′,O′′)(4-imidazol-1-yl-pyridine-κN)copper(II)], C15H9N4O4ICu
  14. Crystal structure of polybis(μ 4-3,5-dicarboxylatopyrazol-1-yl)-bis(N,N-dimethylformamide)tri-copper(II)–acetonitrile (1/2), C20H22Cu3N8O10
  15. Crystal structure of poly[(μ2-5-hydroxy-isophthalato-κ4O,O′:O″,O‴)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)cadmium(II)], C21H24CdN4O5
  16. The crystal structure of poly[bis(μ2-1,4-bi(1-imidazolyl)benzene-κ2N:N′)bis(μ2-4,4′-methylenebis(3-hydroxy-2-naphthoate)-κ2O:O′)cobalt(II)], C35H24CoN4O6
  17. The crystal structure of a cobalt-vanadium-oxido hydrate
  18. The crystal structure of catena-poly[(μ 2-2H-1,2,3-triazole-4,5-dicarboxylato-κ 2 O, O′)-(μ 2-1,3-bis((1H-imidazol-1-yl)methyl)benzene-κ 2 N,N′) zinc(II)], C18H15N7O4Zn
  19. Crystal structure of poly[diaqua-(bis(m2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′-manganese] dichloride, C28H32MnN8O2Cl2
  20. The crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino [3,2-a]isoquinolin-7-ium (E)-3-(4-nitrophenyl)acrylate pentahydrate, C29H34N2O13
  21. Crystal structure of poly[(μ6-ammoniotris(methylene))tris(hydrogen phosphonato)cadmium(II)], C3H10CdNO9P3
  22. Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2
  23. The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2
  24. Crystal structure of (E)-2-(2-(4-(diethylamino)styryl)-1-ethyl-1,4-dihydroquinolin-4-yl) malononitrile, C26H26N4
  25. Crystal structure of ethyl 2-((2,6-dichloro-4-(cyanomethyl)phenyl) amino)benzoate, C17H14Cl2N2O2
  26. Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3
  27. The crystal structure of bis(acetonitrile-κ1N)tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)rhodium(II) (Rh–Rh), C32H18F8O8N2Rh2
  28. The crystal structure of a new polymorph of 6-hydroxy-2-naphthoic acid, C11H8O3
  29. The crystal structure of [(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)-2,2′-bipyridine-κ2N-copper(II)] tetrahydrate, C22H23N3O9Cu
  30. The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
  31. Crystal structure of 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one, C10H10O2
  32. Crystal structure of bis(tetrapropylammonium) dodecacarbonyltetratelluridotetraferrate(2-), (Pr4N)2[Fe4Te4(CO)12]
  33. The crystal structure of poly[bis(μ2−3−aminopyridine−4−carboxylato−κ2N:O)Zinc(II)], [Zn(C6H5N2O2)2] n
  34. The crystal structure of methyl 5-nitro-2-(tosyloxy)benzoate, C15H13NO7S
  35. The crystal structure of 18-crown-6 ― tetraaqua-dichlorido-di-μ2-chloridodicopper(II) (2/1), C12H32O10Cu2Cl4
  36. Crystal structure of 6,6a,7,8,9,10-hexahydro-5H-pyrazino [2,3-e]pyrido[1,2-a]pyrazine, C10H14N4
  37. Crystal structure of catena-poly-{diaqua-bis[μ-(((4-chlorophenyl)sulfonyl)glycinato-κO)](μ2-4, 4′-bipyridine-κ2N:N′)cobalt(II)} dihydrate, C26H30Cl2CoN4O12S2
  38. Crystal structure of bis{N′-[1,3-diphenylprop-2-en-1-ylidene]-N-phenylcarbamohydrazonothioato}zinc(II), C44H36N6S2Zn
  39. Crystal structure of tetraaqua-bis(((4-chlorophenyl)sulfonyl)glycinato-κO)cobalt(II) dihydrate, C16H26Cl2CoN2O14S2
  40. Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
  41. Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
  42. Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  43. Crystal structure of (2-phenylimino methylquinoline-κ 2 N,N′)-bis(1–phenylpyrazole-κ 2 C,N)-iridium(III) hexafluorophosphate, C34H26F6IrN6P
  44. Crystal structure of (3-hydroxy-4-methoxyphenyl)(pyrrolidin-1-yl)methanone, C12H15NO3
  45. The crystal structure of bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)] C6H18O2S2NaInBr6
  46. Crystal structure of N-cyclopropyl-3-hydroxy-4-methoxybenzamide, C11H13NO3
  47. The crystal structure of (bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″ )-(dihydrogen L-malate-κ2O,O ′)copper(II) perchlorate dihydrate, CuC20H24ClN5O12
  48. Crystal structure of (1E,1′E)-4,4′-(9,9-diethyl-9H-fluorene-2,7-diyl)dibenzaldehyde dioxime, C31H28N2O2
  49. Crystal structure of diethyl 1,9-bis(4-fluorophenyl)-4,6-diphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta [b]pyridine-3,7(2H)-dicarboxylate, C40H36F2N2O4
  50. Crystal structure of bis(benzene-1 carboxylato-O 3,5-carboxyl-κ1O)-[(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) ─ benzene-1,3,5-tricarboxylic acid ─ water (1/2/4), C52H66N4NiO28
  51. Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
  52. Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
  53. Crystal structure of 1,4-dibromo-2,5-bis(prop-2-yn-1-yloxy)benzene, C12H8Br2O2
  54. Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl carbonothioate, C24H15NO2S2
  55. The crystal structure of (E)-4-fluoro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
  56. Crystal structure of (E)-1-(benzo[d]thiazol-2-yl)-N-(4,5-dihydropyren-2-yl)methanimine, C24H16N2S
  57. Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
  58. Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H52FNO3
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