Home The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S
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The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S

  • Yaoyao Li , Lai Su , Tianqin Wang and Le Zhang ORCID logo EMAIL logo
Published/Copyright: November 27, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 1

Abstract

C19H21NO5S, triclinic, P1̄ (no. 2), a = 8.428(2) Å, b = 10.638(3) Å, c = 11.177(3) Å, α = 63.125(4)∘, β = 77.819(4)∘, γ = 79.845(4)∘, V = 869.9(4) Å3, Z = 2, R gt (F) = 0.0472, wR ref (F 2 ) = 0.1379, T = 296(2) K.

CCDC no.: 2402219

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: 0.26 × 0.21 × 0.17 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.22 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: 4,474, 3,098, 0.030
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2,490
N(param)refined: 238
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 0.5943 (3) 0.3812 (2) 0.2334 (2) 0.0349 (5)
H1 0.492167 0.433531 0.252907 0.042*
C2 0.6903 (3) 0.3345 (2) 0.3491 (2) 0.0336 (5)
C3 0.6277 (3) 0.3638 (3) 0.4591 (2) 0.0406 (5)
H3 0.524623 0.412030 0.462298 0.049*
C4 0.7142 (3) 0.3232 (3) 0.5644 (2) 0.0421 (6)
H4 0.670848 0.343842 0.637869 0.051*
C5 0.8661 (3) 0.2514 (2) 0.5587 (2) 0.0358 (5)
C6 0.9305 (3) 0.2179 (3) 0.4514 (2) 0.0412 (5)
H6 1.032602 0.167977 0.449204 0.049*
C7 0.8413 (3) 0.2594 (3) 0.3482 (2) 0.0400 (5)
H7 0.883629 0.236440 0.275926 0.048*
C8 1.1271 (3) 0.3195 (3) 0.6247 (3) 0.0536 (7)
H8A 1.198781 0.294517 0.690007 0.080*
H8B 1.074803 0.413113 0.604913 0.080*
H8C 1.188825 0.317072 0.543038 0.080*
C9 0.6863 (3) 0.4797 (2) 0.0996 (2) 0.0360 (5)
C10 0.7498 (3) 0.4367 (3) 0.0009 (2) 0.0389 (5)
C11 0.6251 (3) 0.2185 (2) 0.1245 (2) 0.0377 (5)
C12 0.5522 (2) 0.2549 (2) 0.2244 (2) 0.0351 (5)
C13 0.6988 (3) 0.6171 (3) 0.0925 (2) 0.0431 (6)
C14 0.8341 (4) 0.8255 (3) −0.0166 (3) 0.0639 (8)
H14A 0.906654 0.874566 −0.097903 0.096*
H14B 0.881599 0.808213 0.060987 0.096*
H14C 0.732024 0.882371 −0.016722 0.096*
C15 0.8463 (3) 0.5190 (3) −0.1336 (2) 0.0516 (6)
H15A 0.953059 0.525964 −0.121040 0.077*
H15B 0.792093 0.612155 −0.175583 0.077*
H15C 0.855636 0.471622 −0.190667 0.077*
C16 0.6005 (3) 0.0867 (3) 0.1183 (3) 0.0484 (6)
H16A 0.704216 0.046578 0.087225 0.058*
H16B 0.527591 0.109238 0.053425 0.058*
C17 0.5299 (4) −0.0209 (3) 0.2551 (3) 0.0586 (7)
H17A 0.493847 −0.096129 0.243887 0.070*
H17B 0.614104 −0.062287 0.312848 0.070*
C18 0.3902 (3) 0.0428 (3) 0.3220 (3) 0.0560 (7)
H18A 0.358331 −0.027069 0.413737 0.067*
H18B 0.298355 0.067100 0.273390 0.067*
C19 0.4274 (3) 0.1728 (3) 0.3274 (2) 0.0408 (5)
N1 0.7275 (2) 0.3049 (2) 0.01943 (19) 0.0425 (5)
H1A 0.781076 0.274881 −0.038597 0.051*
O1 0.8074 (2) 0.6945 (2) −0.01074 (19) 0.0596 (5)
O2 0.6245 (2) 0.6584 (2) 0.1738 (2) 0.0631 (5)
O3 0.3511 (2) 0.2105 (2) 0.41209 (18) 0.0578 (5)
O4 1.0599 (2) 0.0617 (2) 0.71842 (19) 0.0590 (5)
O5 0.8746 (2) 0.2186 (2) 0.80022 (18) 0.0638 (6)
S1 0.97971 (7) 0.19934 (7) 0.69068 (5) 0.0433 (2)

1 Source of materials

All reagents were commercial and used directly without any purification. The targeted compound was synthesized via a concise one-pot method. A mixture containing 1 mmol 1,3-cyclohexanedione, 1 mmol methyl 3-aminocrotonate, and 1 mmol 4-methylsulphonyl benzaldehyde was thoroughly combined in a 50 mL solution of anhydrous ethanol. The mixture was heated to a temperature of 333 K and maintained at this level for 6 h. Upon completion of the reaction, the mixture was allowed to cool to room temperature, at which point the resulting precipitate was collected. The precipitate was recrystallized in 95 % ethanol, yielding 58.4 % (based on 4-methylsulphonyl benzaldehyde). The colorless block crystals were isolated.

2 Experimental details

The structure was solved by Direct Methods with the SHELXTL-2018 program. All H-atoms from C and atoms were positioned with idealized geometry and refined isotropically (U iso(H) = 1.2 U eq(C) or U eq(N)) using a riding model.

3 Comment

To date, the single-crystal structures of 4-phenyl-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate 5 and some 4-(mono- or multi-substituted-phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate have been reported elsewhere, such as methyl 2-methyl-4-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, 6 methyl 4-(3-bromo-4- fluorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline- 3-carboxylate, 7 ethyl 2-methyl-5-oxo-4-(2,3,4-trimethoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, 8 etc. 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17

As shown in the figure, the asymmetric unit is made of a one molecule of the title compound, methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate. Notably, the phenyl group is coplanar and the S atom is in tetrahedral configuration. Neighbouring ketone ring adopts a flattened chair conformation. Intermolecularly, an infinitely supramolecular chain facilitated by a network of hydrogen bonds involving the N1···H1A···O5 interaction is found. All bond lengths and angles within this structure align closely with those reported for analogous compounds. 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17

Corresponding author: Le Zhang, Guo Rui Yinuo Drug Safety Evaluation Research Co., Ltd, Xi’an, Shaanxi, China, E-mail:

Funding source: the Foundation of Shaanxi province Qin Chuangyuan Project

Award Identifier / Grant number: 2024QCY-KXJ-058

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

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

  3. Research funding: This work was funded by the Foundation of Shaanxi province Qin Chuangyuan Project (no. 2024QCY-KXJ-058).

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Received: 2024-10-14
Accepted: 2024-11-13
Published Online: 2024-11-27
Published in Print: 2025-02-25

© 2024 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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https://doi.org/10.1515/ncrs-2024-0409
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
  4. Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
  5. Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
  6. Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
  7. Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
  8. Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
  9. The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
  10. The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
  11. The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
  12. The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
  13. Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  14. The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
  15. The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
  16. Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
  17. The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
  18. Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
  19. The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
  20. The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
  21. Crystal structure of (−)-flavesine H, C15H22N2O2
  22. Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
  23. Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
  24. The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
  25. The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
  26. Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
  27. The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
  28. The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
  29. The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
  30. Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
  31. Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
  32. Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
  33. Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
  34. Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
  35. Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
  36. The crystal structure of 1,1,1,2,2,2-hexakis(2-methyl-2-phenylpropyl)distannane,C60H78Sn2
  37. The crystal structure of (2,7-dimethoxynaphthalene-1,8-diyl)bis((3-nitrophenyl)methanone), C26H18N2O8
  38. Crystal structure of diaqua-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II) dinitrate dihydrate, C60H76Cl8N14O14Zn
  39. The crystal structure of diphenyl bis(2-((diphenoxyphosphoryl)amino)ethyl)phosphoramidate monohydrate C40H42N3O10P3
  40. Crystal structure of 4,4′-bis(dibromomethyl)-1,1′-biphenyl, C14H10Br4
  41. Crystal structure of CaPtZn
  42. Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2
  43. The crystal structure of (3′-(2-bromophenyl)-2-phenyl-[2,2′-bioxiran]-3-yl)(phenyl)methanone, C92H68O12Br4
  44. Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2
  45. The crystal structure of bis(selenocyanato-κ1 N)-bis(methanol)-bis((1E,2E)-1,2-bis (1-(pyridin-4-yl)ethylidene)-hydrazine)iron(II) methanol solvate, C34H44FeN10O4Se2
  46. Crystal structure of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(5-(4-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one, C26H21BrN2O4
  47. The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S
  48. Crystal structure of 1′,3′-dihydro-2,2′-spirobi[indene]-1,3-dione, C17H12O2
  49. Crystal structure of (E)-2,2′,3,3′-tetrahydro-[1,1′-biindenylidene]-4,4′-diol, C18H16O2
  50. Crystal structure of di-glycylglycinium squarate dihydrate, C12H22N4O12, at 105 K
  51. Crystal structure of {[(4-fluorophenyl)methyl]triphenylphosphonium}dibromocopper(I), [C25H21FP]+[CuBr2]−
  52. Crystal structure of poly[diaqua-bis(μ2-5-((pyridin-4-yl-methyl)amino)benzene-1,3-dicarboxylato-κ 2 N:O)cadmium(II)], C28H26CdN4O10
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