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Crystal structure of diethyl-2,2′-naphthalene-2,3-diylbis(oxy)diacetate, C18H20O6

  • Peipei Li , Yu Huang ORCID logo EMAIL logo , Yanru Fan and Hao Wang
Published/Copyright: April 1, 2021
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 4

Abstract

C18H20O6, monoclinic, C2/c (no. 15), a = 27.191(3) Å, b = 8.7442(3) Å, c = 20.861(2) Å, β = 136.337(18)°, V = 3424.5(9) Å3, Z = 8, Rgt(F) = 0.0553, wRref(F2) = 0.1625, T = 294.7(4) K.

CCDC no.: 2049322

The molecular structure is shown in the Figure (H atoms omitted for clarity). 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:Colourless block
Size:0.80 × 0.60 × 0.40 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:0.81 mm−1
Diffractometer, scan mode:New Gemini, ω
θmax, completeness:67.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:9228, 3054, 0.038
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2514
N(param)refined:220
Programs:CrysAlisPRO [1], Olex2 [2], SHELX [3], [4]
Table 2:

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

AtomxYzUiso*/Ueq
C10.70609 (12)0.3858 (3)0.53645 (18)0.0869 (7)
H10.7538630.3581070.5793840.104*
C20.66062 (14)0.3371 (3)0.4474 (2)0.0986 (8)
H20.6774600.2758980.4300720.118*
C30.58920 (14)0.3777 (3)0.38181 (19)0.0961 (7)
H30.5584200.3443320.3207710.115*
C40.56415 (11)0.4668 (3)0.40707 (16)0.0824 (6)
H40.5162600.4939480.3626570.099*
C50.60942 (9)0.5181 (2)0.49894 (13)0.0640 (5)
C60.68225 (9)0.4773 (2)0.56497 (14)0.0658 (5)
C70.72881 (9)0.5284 (2)0.65724 (14)0.0672 (5)
H70.7765320.5000980.7009480.081*
C80.70512 (8)0.61839 (19)0.68332 (12)0.0597 (4)
C90.82028 (9)0.6529 (3)0.83588 (14)0.0796 (6)
H9A0.8289700.5444360.8382900.096*
H9B0.8418270.6827090.8965660.096*
C100.85683 (9)0.7379 (3)0.81734 (14)0.0808 (6)
C110.84294 (16)0.9090 (3)0.7163 (2)0.1076 (9)
H11A0.8923690.9364230.7700290.129*
H11B0.8162891.0021980.6833580.129*
C120.8376 (2)0.8085 (4)0.6553 (3)0.1340 (12)
H12A0.7888630.7791460.6030730.201*
H12B0.8661260.7187760.6890630.201*
H12C0.8544920.8616160.6339030.201*
C130.58555 (8)0.6098 (2)0.52822 (13)0.0646 (5)
H130.5376810.6363970.4858230.077*
C140.63181 (8)0.65939 (19)0.61756 (12)0.0578 (4)
C150.54372 (9)0.8002 (2)0.58966 (13)0.0668 (5)
H15A0.5116360.7132810.5585130.080*
H15B0.5329520.8651530.5430810.080*
C160.53376 (10)0.8884 (2)0.64165 (14)0.0715 (5)
C170.44745 (14)1.0356 (3)0.6161 (2)0.1037 (8)
H17A0.4745911.1297170.6444700.124*
H17B0.4559630.9763530.6626950.124*
C180.37019 (15)1.0702 (3)0.5367 (2)0.1072 (9)
H18A0.3621541.1255660.4900920.161*
H18B0.3548791.1309200.5580610.161*
H18C0.3436770.9762940.5108260.161*
O10.81488 (7)0.83241 (18)0.74630 (11)0.0825 (5)
O20.91876 (7)0.7185 (3)0.86449 (13)0.1250 (8)
O30.74588 (6)0.67649 (16)0.77010 (9)0.0685 (4)
O40.61486 (6)0.74946 (15)0.65319 (9)0.0681 (4)
O50.57577 (9)0.8984 (2)0.72388 (12)0.1067 (6)
O60.46894 (7)0.94902 (18)0.58027 (10)0.0793 (4)

Source of material

The ethylbromoacetate (8.35 ml, 75 mmol) was added dropwise into the mixture of K2CO3 (20.70 g, 150 mmol) and naphthalene-2,3-diol (4.8 g, 30 mmol) in acetonitrile (150 ml). The reaction solution was refluxed for 24 h, and then it was cooled to room temperature. The insoluble solid was filtered off, and the filtrate was concentrated to obtain the crude product, which was recrystallized from ethyl acetate/petroleum ether the product as a white solid (6.40 g, 79%). 1HNMR (400 MHz, CDCl3) δ ppm: 8.16–8.18 (dd, J1 = 3.6 Hz, J2 = 6 Hz, 2H, Ar-H), 7.72–7.74 (dd, J1 = 3.6 Hz, J2 = 6 Hz, 2H, Ar-H), 7.23 (s, 2H, Ar-H), 4.78 (s, 4H, OCH2), 4.25–4.31 (q, 4H, COOCH2), 1.28–1.32 (t, J = 7.2 Hz, 6H, COOCH2CH3); 13C NMR (400 MHz, CDCl3)δ ppm: 182.91, 168.78, 153.69, 134.13, 133.70, 126.74, 124.83, 124.04, 68.19,61.67, 14.32; HRMSm/z: (M + Na+) 355.1149, calculated for 355.1158. Crystals of the title compound were obtained from the solvents (ethylacetate: petroleum ether = 1:4).

Experimental details

Comment

To design different crown ether compounds is always a research hotspot. Diethyl-2,2-(naphthalene-2,3-diylbis(oxy)) diacetate is the synthetic intermediate of some macrocyclic compounds [5], [6], [7]. These macrocyclic compounds, especially naphtha-aza-crown ethers (NACEs), exhibited excellent coordination ability with different metal ions. Hence, NACEs have the potential to be used as receptors in molecular recognition, catalysts, separation and so on. Recently, we synthesized some NACEs by cyclocondensating of diethyl-2,2-(naphthalene-2,3-diylbis(oxy)) diacetate with different diamines. The ion selectivities of the NACEs were studied by the square wave voltammetry [8]. Comparing with the optimized structures of NACEs calculated by the density functional theory and the crystal structure of diethyl-2,2-(naphthalene-2,3-diylbis(oxy)) diacetate, the rigid naphthalene ring influenced the structure of the crown ether which played an important role in the ion selectivity.

The crystal structure clearly indicated the chemical structure and configuration of diethyl-2,2-(naphthalene-2,3-diylbis(oxy))diacetate, and all the intramolecular bond lengths and angles are in the expected ranges. The Cambridge Structural Database was searched and five structural related compounds were found [9], [10], [11]. By comparison with these compounds, it was observed that the title compound contains a unique naphthalene ring as the center core, which causes one of the two ester side chains to be coplanar with the naphthalene ring, while in the other compounds, both ester side chains are located on the same side of the aryl moiety.

Corresponding author: Yu Huang, School of Pharmacy, Ningxia Medical University, Yinchuan, Ningxia, China, E-mail:

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 81773582

Funding source: Key R&D Program of Ningxia, China

Award Identifier / Grant number: 2018BFG02004

Funding source: the Program for Leading Talents of Ningxia Province, China

Award Identifier / Grant number: KJT2018004

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

  2. Research funding: National Natural Science Foundation of China (81773582), the Key R&D Program of Ningxia, China (2018BFG02004), the Program for Leading Talents ofNingxia Province, China (KJT2018004).

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

References

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Received: 2021-02-10
Accepted: 2021-03-12
Published Online: 2021-04-01
Published in Print: 2021-07-27

© 2021 Peipei Li et al., 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[(μ2-aqua-tetraaqua-(μ3-glutarato-κ4O,O′:O′:O′′)-(μ5-glutarato-κ6O:O,O′:O′:O′′:O′′′)distrontium(II)], C10H22O13Sr2
  4. The crystal structure of acetato-κ1O-{(2-(2-(2-aminophenoxy)ethoxy)phenyl)(4-oxo-4-phenylbut-2-en-2-yl)amido-κ2N,N′,O}copper(II), C26H26CuN2O5
  5. Crystal structure of dimethanolato-k2O:O-bis(1-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN)-bis(thiocyanato-κN)dicopper(II), C34H32Cu2N12O2S2
  6. Crystal structure of poly[diaqua-bis(μ2-3-(pyrimidin-5-yl)benzoato-κ2N:O)cobalt(II)] dihydrate, [Co(C11H11O2N2)2(H2O)2]
  7. Crystal structure of bis(3,3-dimethyl-1-phenylbut-1-en-2-yl)(trimethylsilyl)amido-k1N)zinc(II), Zn(C15H24NSi)2
  8. Crystal structure of catena-poly[(μ2-methanolato-κ2O:O)-(μ2-1-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)-(thiocyanato-κ1N)copper(II)] 0.25 hydrate, C17H16CuN6OS ⋅ 0.5H2O
  9. The crystal structure of 2-amino-5-nitroanilinium iodide monohydrate, C6H8IN3O2
  10. The crystal structure of 3-amino-5-carboxypyridin-1-ium perchlorate monohydrate, C6H9ClN2O7
  11. Crystal structure of 7-hydroxy-2,4-dimethoxy-9,10-dihydrophenanthrene from Arundina graminifolia, C16H16O3
  12. Crystal structure of 6,6′-((1E, 1′E)-(((1R, 2R)-1,2-diphenylethane-1,2-diyl) bis(azanylylidene))bis(methanylylidene))bis(2-ethylphenol), C32H32N2O2
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  26. Crystal structure of benzo[d][1,3]dioxol-5-yl-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18O5
  27. The crystal structure of ethyl 5-methyl-7-(4-(phenylthio)phenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C20H19N5O2S
  28. Crystal structure of N′,N‴-((propane-2,2-diylbis(1H-pyrrole-5,2-diyl))bis(methaneylylidene))-di(isonicotinohydrazide)– water – dimethylformamide (1/4/2), C25H24N8O2·4H2O·2C3H7NO
  29. Synthesis and crystal structure of 4-(2,4-dinitrophenoxy)benzaldehyde, C13H8N2O6
  30. The crystal structure of 1-dodecylpyridin-1-ium bromide monohydrate, C17H32BrNO
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https://doi.org/10.1515/ncrs-2021-0061
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of poly[(μ2-aqua-tetraaqua-(μ3-glutarato-κ4O,O′:O′:O′′)-(μ5-glutarato-κ6O:O,O′:O′:O′′:O′′′)distrontium(II)], C10H22O13Sr2
  4. The crystal structure of acetato-κ1O-{(2-(2-(2-aminophenoxy)ethoxy)phenyl)(4-oxo-4-phenylbut-2-en-2-yl)amido-κ2N,N′,O}copper(II), C26H26CuN2O5
  5. Crystal structure of dimethanolato-k2O:O-bis(1-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN)-bis(thiocyanato-κN)dicopper(II), C34H32Cu2N12O2S2
  6. Crystal structure of poly[diaqua-bis(μ2-3-(pyrimidin-5-yl)benzoato-κ2N:O)cobalt(II)] dihydrate, [Co(C11H11O2N2)2(H2O)2]
  7. Crystal structure of bis(3,3-dimethyl-1-phenylbut-1-en-2-yl)(trimethylsilyl)amido-k1N)zinc(II), Zn(C15H24NSi)2
  8. Crystal structure of catena-poly[(μ2-methanolato-κ2O:O)-(μ2-1-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)-(thiocyanato-κ1N)copper(II)] 0.25 hydrate, C17H16CuN6OS ⋅ 0.5H2O
  9. The crystal structure of 2-amino-5-nitroanilinium iodide monohydrate, C6H8IN3O2
  10. The crystal structure of 3-amino-5-carboxypyridin-1-ium perchlorate monohydrate, C6H9ClN2O7
  11. Crystal structure of 7-hydroxy-2,4-dimethoxy-9,10-dihydrophenanthrene from Arundina graminifolia, C16H16O3
  12. Crystal structure of 6,6′-((1E, 1′E)-(((1R, 2R)-1,2-diphenylethane-1,2-diyl) bis(azanylylidene))bis(methanylylidene))bis(2-ethylphenol), C32H32N2O2
  13. The crystal structure of 2-amino-5-carboxypyridin-1-ium iodide monohydrate, C6H9IN2O3
  14. The crystal structure of 2-(3,5-difluorophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, C16H11BF2N2
  15. Crystal structure of bis{(2-pyridinyl)-1-phenyl-1-isopropylmethanolato-κ2N,O}nickel, C30H32N2NiO2
  16. Crystal structure of poly[(m3-3-carboxyadamantane-1-carboxylato-κ3O:O′:O″)-(phenanthroline-κ2N,N′)sodium(II)], C24H23N2NaO4
  17. Crystal structure of 2-phenylethynyl-1,3,6,8-tetramethylBOPHY (BOPHY = bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C22H20B2F4N4
  18. Crystal structure of 4-tert-butyl-2-N-(2-pyridylmethyl)aminophenol, C16H20N2O
  19. The crystal structure of (3Z,3′Z)-4,4′-((1,4-phenylenebis(methylene))bis(azanediyl))bis(pent-3-en-2-one), C18H24N2O2
  20. Crystal structure of (morpholine-1-carbodithioato-κ2-S,S′)bis(triphenylphosphine-κ-P)gold(I), C41H38AuNOP2S2
  21. Crystal structure of 1,4-bis(4-bromobenzyl)-4-(4-chlorophenyl)-1,4-dihydropyridine-3-carbonitrile, C26H19Br2ClN2
  22. The crystal structure of fac-tricarbonyl (N′-benzoyl-N,N-diphenylcarbamimidothioato-κ2S,O)-(pyrazole-κN)rhenium(I) — methanol (1/1) C26H23O4N4SRe
  23. The crystal structure of Ba2Mn(SeO3)2Cl2 containing 1∞[Mn(SeO3)2Cl2]4− chains
  24. Crystal structure of 3,3′,3″-((1E,1′E,1″E)-((nitrilotris(ethane-2,1-diyl))tris(azaneylylidene)) tris(methaneylylidene))tris(4-hydroxy-1-naphthaldehyde) monohydrate, C42H36N4O6·H2O
  25. The crystal structure of 4-(6-acetyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidin-7-yl)benzonitrile, C14H12N6O
  26. Crystal structure of benzo[d][1,3]dioxol-5-yl-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18O5
  27. The crystal structure of ethyl 5-methyl-7-(4-(phenylthio)phenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C20H19N5O2S
  28. Crystal structure of N′,N‴-((propane-2,2-diylbis(1H-pyrrole-5,2-diyl))bis(methaneylylidene))-di(isonicotinohydrazide)– water – dimethylformamide (1/4/2), C25H24N8O2·4H2O·2C3H7NO
  29. Synthesis and crystal structure of 4-(2,4-dinitrophenoxy)benzaldehyde, C13H8N2O6
  30. The crystal structure of 1-dodecylpyridin-1-ium bromide monohydrate, C17H32BrNO
  31. Crystal structure of (E)-amino(2-(4-(dimethylamino)benzylidene)hydrazineyl)methaniminium nitrate, C10H16N6O3
  32. Crystal structure of (E)-(2-((1H-pyrrol-2-yl)methylene)hydrazineyl)(amino)methaniminium nitrate monohydrate, C6H12N6O4
  33. The crystal structure of hexakis(1-propylimidazole-κ1N)copper(II) dichloride, C36H60Cl2CuN12
  34. The crystal structure of bis{(μ2-3,3-dimethyl-1-phenylbut-1-en-2-yl)((dimethylamino)dimethylsilyl)amido-κ3N,N′:N′}dilithium, C32H54Li2N4Si2
  35. The crystal structure of methyl 4-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)benzoate, C18H15BN2O2
  36. Crystal structure of (E)-N-(1-((2-chlorothiazol-5-yl)methyl)pyridin-2(1H)-ylidene)-2,2,2-trifluoroacetamide, C11H7ClF3N3OS
  37. Crystal structure of N′, N‴-((propane-2,2-diylbis(1H-pyrrole-5,2-diyl))bis (methaneylylidene))di(picolinohydrazide) – water – methanol (1/1/1), C25H24N8O2·H2O·CH3OH
  38. Crystal structure of 3-(2-chloro-benzyl)-7-[4-(2-chloro-benzyl)-piperazin-1-yl]-5,6,8-trifluoro-3H-quinazolin-4-one, C26H21Cl2F3N4O
  39. Crystal structure of N1,N2-bis(2-fluorobenzyl)benzene-1,2-diamine,C20H18F2N2
  40. The crystal structure of 2-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, C17H13BN2O2
  41. The crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene)) bis(2-bromo-4-nitrophenol) — dimethylsulfoxide (1/2), C14H8Br2N4O6⋅2(C2H6OS)
  42. Selective biocatalytic synthesis and crystal structure of (2R,6R)-hydroxyketaminium chloride, C13H17Cl2NO2
  43. Crystal structure of bis{tetraaqua-[μ3-1-(4-carboxylatophenyl)-5-methyl-1H-pyrazole-3-carboxylate-κ4N,O,O′,O″] [μ2-1-methyl-1H-pyrazole-3,5-dicarboxylate-κ3N,O:O]dicobalt(II)} dihydrate, C36H44Co4N8O26
  44. Crystal structure of diethyl-2,2′-naphthalene-2,3-diylbis(oxy)diacetate, C18H20O6
  45. Synthesis and crystal structure of poly[(μ3-2-(2-carboxylatophenyl)-1H-benzo[d]imidazole-5-carboxylato-κO,O′:O′;:O″, O″′)-(μ2-1-(4-(1Himidazol-1-yl)phenyl)-1H-imidazole-κ2N:N′)cadmium(II)], C27H18CdN6O4
  46. The crystal structure of catena-poly[diaqua-bis(μ2-2-((2-(2-phenylacetyl)hydrazineylidene)methyl)benzoato-κ2O:O')zinc(II)], C32H30N4O8Zn
  47. The crystal structure of 2-(3,4-dimethoxyphenyl)-2,3-dihydro-1H-naphtho [1,8-de][1,3,2]diazaborinine, C18H17BN2O2
  48. The crystal structure of hexakis(1-ethylimidazole-κ1N)nickel(II) dichloride – 1-ethylimidazole (1/2), C40H64Cl2NiN16
  49. Crystal structure of diaqua-bis(2,4-dinitrophenolato-κ2O,O′)copper(II) 1.5 hydrate, C12H13CuN4O13.5
  50. Crystal structure of N′,N‴-((1E,1′E)-((decane-1,10-diylbis(oxy))bis(2,1-phenylene)) bis(methaneylylidene))di(isonicotinohydrazide), C36H40N6O4
  51. The crystal structure of 2-[(R)-1-(naphthalen-1-yl)ethyl]-2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1(6H)-one, C19H20NO2
  52. Synthesis and crystal structure of (1E,2E)-3-(anthracen-9-yl)-1-(4-methoxyphenyl)prop-2-en-1-one oxime, C24H19NO2
  53. Synthesis and crystal structure of (2E,2′E)-3,3′-(1,3-phenylene)bis(1-(3-bromophenyl)prop-2-en-1-one), C24H16Br2O2
  54. The crystal structure of catena-poly[bis(µ2-1,2-bis((1H-imidazol-1-yl)methyl)benzene- κ2N:N′)-bis(nitrato-κO)copper(II)], C28H28N10O6Cu
  55. Synthesis and crystal structure of the novel chiral acetyl-3-thiophene-5-(9-anthryl)-2-pyrazoline, C23H18N2OS
  56. Crystal structure of (E)-3-(dimethylamino)-1-(thiophen-3-yl)prop-2-en-1-one, C9H11NOS
  57. Crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O′)-(μ2-4-amino-4H-1,2,4-triazole-κ2N:N′) copper(II)], C9H8N5O5CuI
  58. Crystal structure of cyclopropane-1,2,3-triyltris(phenylmethanone), C24H18O3
  59. Crystal structure of bis(amino(thioureido)methaniminium) terephthalate, C12H18N8O4S2
  60. A three-dimensional Eu(III) framework in the crystal structure of dimethylaminium poly[dimethylformamide-κ1N)bis(μ4-terephthalato-κ4O:O′:O′′:O′′′)europium(III)] monohydrate, C21H25EuN2O10
  61. Crystal structure of 2-methoxyphenyl 2-(6-methoxynaphthalen-2-yl)propanoate, C21H20O4
  62. The crystal structure of Hexakis(diethylamido)dimolybdenum, Mo2(NEt2)6
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