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Crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3-methoxybenzoate, C13H16O6

  • Liu Shu-Juan , Guo Chun-Mei , Wang Gui-Shu , Li Wen-Jing and Nie Xu-Liang ORCID logo EMAIL logo
Published/Copyright: December 4, 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

C13H16O6, monoclinic, P21/c (no. 14), a = 12.180(3) Å, b = 13.813(4) Å, c = 7.842(2) Å, β = 93.917(4)°, V = 1316.2(6) Å3, Z = 4, R gt (F) = 0.0442, wR ref (F2) = 0.1375, T = 296(2) K.

CCDC no.: 2309927

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: 0.21 × 0.16 × 0.14 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.11 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 25.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 9947, 2447, 0.044
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 1662
N(param)refined: 175
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 1.28321 (19) 0.3571 (2) 0.5413 (3) 0.0674 (7)
H1A 1.2629 0.3236 0.6417 0.101*
H1B 1.3261 0.4132 0.5743 0.101*
H1C 1.3258 0.3148 0.4744 0.101*
C2 1.12135 (17) 0.31513 (16) 0.3775 (3) 0.0477 (5)
C3 1.02163 (16) 0.35245 (14) 0.2804 (2) 0.0441 (5)
C4 1.00042 (17) 0.44978 (15) 0.2588 (3) 0.0495 (5)
H4 1.0496 0.4950 0.3079 0.059*
C5 0.90706 (17) 0.48103 (15) 0.1652 (3) 0.0485 (5)
H5 0.8937 0.5470 0.1514 0.058*
C6 0.83343 (16) 0.41457 (14) 0.0921 (2) 0.0421 (5)
C7 0.85325 (16) 0.31470 (14) 0.1161 (2) 0.0416 (5)
C8 0.94684 (16) 0.28495 (14) 0.2085 (2) 0.0440 (5)
H8 0.9606 0.2192 0.2234 0.053*
C9 0.78584 (19) 0.15443 (15) 0.0721 (3) 0.0552 (6)
H9A 0.8515 0.1315 0.0242 0.083*
H9B 0.7231 0.1212 0.0194 0.083*
H9C 0.7905 0.1423 0.1929 0.083*
C10 0.71362 (17) 0.53521 (15) −0.0291 (3) 0.0487 (5)
H10A 0.7719 0.5674 −0.0855 0.058*
H10B 0.7063 0.5664 0.0804 0.058*
C11 0.60800 (18) 0.54243 (15) −0.1364 (3) 0.0510 (5)
C12 0.47585 (17) 0.65324 (16) −0.2522 (3) 0.0551 (6)
H12A 0.4154 0.6292 −0.1898 0.066*
H12B 0.4734 0.6214 −0.3627 0.066*
C13 0.46690 (18) 0.76000 (16) −0.2746 (3) 0.0574 (6)
H13A 0.4709 0.7907 −0.1646 0.086*
H13B 0.3979 0.7755 −0.3349 0.086*
H13C 0.5261 0.7827 −0.3389 0.086*
O1 1.14375 (13) 0.23130 (12) 0.3974 (2) 0.0664 (5)
O2 1.18573 (12) 0.38656 (12) 0.4417 (2) 0.0617 (5)
O3 0.73963 (11) 0.43646 (10) −0.00428 (18) 0.0507 (4)
O4 0.77455 (12) 0.25538 (10) 0.04221 (19) 0.0537 (4)
O5 0.55585 (19) 0.47689 (13) −0.1954 (3) 0.1140 (9)
O6 0.58010 (11) 0.63393 (10) −0.15752 (19) 0.0518 (4)

1 Source of materials

The mixture of methyl 4-hydroxy-3-methoxybenzoate (1.82 g, 0.01 mol), ethyl bromoacetate (2.03 g, 0.12 mol), K2CO3 (2.76 g, 0.02 mol) and acetone (10 mL) was reacted at 65 °C for 24 h. After the reaction completed (monitored by TLC), acetone was removed by steam distillation and extracted with ethyl acetate. The colorless product was filtered, and washed with water 3 times respectively. Yield 64.6 % (based on methyl 4-hydroxy-3-methoxybenzoate). Then crystals suitable for X-ray analysis were obtained.

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

Methyl vanillic acid is one of the components of Hovenia dulcis Thunb, which can activate Wnt/β-catenin signaling pathway and induce osteogenic differentiation in vitro, and it is also the raw material and precursor for the synthesis of many drugs and chemical products [5], [6], [7]. Wang et al. have synthesized two 4-alkyl methyl vanillic acid derivatives [8, 9]. Wang et al. also have synthesized methyl 4-(benzyloxy)-3-methoxybenzoate [10]. However, its poor fat solubility and instability hinder its application. So it is necessary to modify their structures. We have synthesized a series of methyl vanillic acid derivatives and reported a crystal structure of methyl 4-acetoxy-3-methoxybenzoate [11].

In the molecule of the title structure bond lengths and angles are very similar to those given in the literature [11–13]. Non-hydrogen atoms in the title compound are approximately planar. The dihedral angles formed by the C3–C8 phenyl plane, the carboxylate group C2–O1–O2 plane and the carboxylate group C11–O5–O6 plane are 1.4(1)°, 3.1(1)° and 2.3(1)°, respectively. The torsion angles of C6–C7–O4–C9, C7–C6–O3–C10, C6–O3–C10–C11 and C11–O6–C12–C13 are −175.6(2)°, 178.3(2)°, −179.6(2)° and −174.6(2)°, respectively.

Corresponding author: Nie Xu-Liang, 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, 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. Competing interests: The authors declare no conflicts of interest regarding this article.

  3. Research funding: This research was supported by the Key Research Foundation of Educational Department of Jiangxi Province of China (GJJ200404), the Research Foundation of Jiangxi Medical Products Administration (2022JS03, 2022JS34), College Students’ Innovation and Entrepreneurship Training Program Project (313).

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Received: 2023-10-30
Accepted: 2023-11-23
Published Online: 2023-12-04
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
  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
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  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
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https://doi.org/10.1515/ncrs-2023-0471
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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
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  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
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  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
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  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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