Startseite Synthesis and crystal structure of dimethyl 4,4′-(propane-1,3-diylbis(oxy))dibenzoate, C19H20O6
Artikel Open Access

Synthesis and crystal structure of dimethyl 4,4′-(propane-1,3-diylbis(oxy))dibenzoate, C19H20O6

  • Li Miao-Miao ORCID logo und Zheng Yan-Ling EMAIL logo
Veröffentlicht/Copyright: 5. April 2024

Abstract

[C19H20O6], monoclinic, C2/c (no. 15), a = 22.467(2) Å, b = 4.9925(5) Å, c = 15.8059(17) Å, β = 108.500(1)°, V = 1681.3(3) Å3, Z = 4, R gt(F) = 0.0309, wR ref(F 2) = 0.0852, T = 296(2) K.

CCDC no.: 2343334

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: 0.20 × 0.14 × 0.11 mm
Wavelength:

μ:
Mo Kα radiation (0.71073 Å)

0.10 mm−1
Diffractometer, scan mode:

θ max, completeness:
Bruker APEX-II, φ and ω

25.5°, >99 %
N(hkl)measured, N(hkl)unique, R int: 6087, 1556, 0.019
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 1337
N(param)refined: 116
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 U iso*/U eq
C1 0.17252 (6) 1.1051 (3) 0.18463 (8) 0.0476 (3)
H1 0.2076 1.2012 0.2180 0.057*
C2 0.14566 (6) 0.9228 (3) 0.22618 (8) 0.0468 (3)
H2 0.1624 0.8962 0.2874 0.056*
C3 0.09332 (5) 0.7772 (2) 0.17685 (7) 0.0407 (3)
C4 0.06890 (5) 0.8137 (3) 0.08525 (8) 0.0432 (3)
H4 0.0345 0.7143 0.0518 0.052*
C5 0.09630 (5) 0.9998 (3) 0.04419 (8) 0.0427 (3)
H5 0.0798 1.0255 −0.0171 0.051*
C6 0.14799 (5) 1.1486 (2) 0.09290 (8) 0.0419 (3)
C7 0.17843 (6) 1.3512 (3) 0.05184 (8) 0.0453 (3)
C8 0.17555 (7) 1.5845 (3) −0.07893 (9) 0.0576 (4)
H8A 0.1777 1.7546 −0.0498 0.086*
H8B 0.1501 1.6006 −0.1403 0.086*
H8C 0.2171 1.5285 −0.0759 0.086*
C9 0.01548 (6) 0.4489 (3) 0.17985 (8) 0.0470 (3)
H9A 0.0244 0.3335 0.1360 0.056*
H9B −0.0196 0.5641 0.1495 0.056*
C10 0.0000 0.2833 (4) 0.2500 0.0502 (4)
H10Aa 0.0355 0.1687 0.2789 0.060*
H10Ba −0.0355 0.1687 0.2211 0.060*
O1 0.14815 (4) 1.38818 (19) −0.03498 (6) 0.0537 (3)
O2 0.22529 (5) 1.4710 (2) 0.09164 (7) 0.0673 (3)
O3 0.06945 (4) 0.60631 (18) 0.22494 (5) 0.0498 (3)
  1. aOccupancy: 0.5.

1 Source of materials

Dissolve methyl 4-hydroxybenzoate (4.56 g, 0.03 mol) in acetonitrile (50 mL), add potassium carbonate (8.28 g, 0.06 mol), stir at 120 °C for an hour, and then add 1,3-dibromopropane (6.05 g, 0.3 mol) to react for 7 h. After the reaction was detected by thin layer chromatography(TLC), the acetonitrile solution was removed by steam distillation and extracted with ethyl acetate. Removal of ethyl acetate produced a colorless product. The product was filtered and washed with water (10 mL) three times. yield 45 % (based on methyl 4-hydroxybenzoate). The product was dissolved in methanol, filtered, and the filtrate was allowed to stand at room temperature. After one week, the crystals 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 U iso(H) = 1.5 U eq(C) for methyl H atoms and 1.2 U eq(C) for all other H atoms.

3 Comment

Recently, the design and synthesis of metal-organic frameworks (MOFs) has become one of the intense research activity, not only owing to their intriguing variety of architectures, but also because of their potential applications as catalysis, molecular sensing, nonlinear optical and fluorescent materials [5], [6], [7], [8]. Over the past few years, aromatic polycarboxylate ligands have been extensively employed in the synthesis of MOFs because of their potential properties and intriguing structural topologies [9]. The multifunctional organic ligands play an important role in constructing MOFs with unique structures and properties [10]. Fan et al. designed and synthesized 3,3′–Dihydr-oxy-4,4′-(propane-1,3-diyldi-oxy)dibenzaldehyde ligand [11]. Förster et al. designed and synthesized a series of three- and hexa-armed benzene derivatives featuring lateral benzoic ester and benzoic acid [12]. Qi et al. and Ma et al. reported the synthesis and crystal structure of two derivativesof ethylene-4,4′-di(oxybenzoic acid) [13, 14]. Hou et al. reported the synthesis and crystal structure of diethyl 4,4′-(butane-1,4-diyldioxy)dibenzoate [15]. Deng et al. reported the synthesis and crystal structure of 3,3′-dimeth-oxy-4,4′-(propane-1,3-diyl-dioxy)dibenzoic acid [16]. Recently, we also reported the synthesis and crystal structure of p-hydroxybenzoic acid derivative methyl 3-methoxy-4-(2-methoxy-2-oxoethoxy)benzoate [17]. We report herein the synthesis and crystal structure of dimethyl 4,4′-(propane-1,3-diylbis(oxy))dibenzoate.

In the molecules of the title structure bond lengths and angles are very similar to those given in the literature [15, 16]. In the title structure, the non hydrogen atoms of p-hydroxyphenylic acid in the title compound are approximately planar. The dihedral angle formed by the C1–C6 phenyl plane and the carboxlate group C7–O1–O2 plane is 4.7(8)° (upper part of the Figure). The two benzene rings in the molecule are almost perpendicular to each other, and the dihedral angle between them is 89.288 (79)°. The torsion angles of C2–C3–O3–C9, C4–C3–O3–C9, C3–O3–C9–C10 and O3–C9–C10–C9 i (Symmetry code: i: −x, y, −z + 1/2) are 179.8(1)°, 0.3(2)°, −179.5(1)° and 60.9(1)°, respectively. Weak intermolecular C–H⋯O hydrogen bonds[C8–H8B⋯O3 ii (Symmetry code: ii: x, −y + 2, z − 1/2.) 2.54 Å, 148.4°] connect two adjacent molecules into one-dimensional chain (lower part of the Figure). In addition, there also exist weak face-to-face π-π stacking interactions between the phenyl rings, which contributes to the stability of the crystal structure.


Corresponding author: Zheng Yan-Ling, Philosophy of Science and Technology, Nanchang Institute of Technology, Nanchang 330044, 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. Research funding: This research was supported by the University–Industry Collaborative Education Program of Ministry of Education of China (No. 230800234154819 and 202101246033), National College Students Innovation and Entrepreneurship Training Program (No. S202312795006X and S20231279503S).

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

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Received: 2024-03-03
Accepted: 2024-03-27
Published Online: 2024-04-05
Published in Print: 2024-06-25

© 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. The crystal structure of tris((Z)-2-hydroxy-N-((E)-pyridin-2-ylmethylene)benzohydrazonato-k2O,N)europium(III), C39H30N9O6Eu
  4. Crystal structure of (E)-3-(benzylideneamino)-2-phenylthiazolidin-4-one, C16H14N2OS
  5. The crystal structure of (E)-4-fluoro-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H15FN2O
  6. Crystal structure of (6-chloropyridin-3-yl)methyl 2-(6-methoxynaphthalen-2-yl)propanoate, C20H18ClNO3
  7. Crystal structure of methyl 3-methoxy-4-(2-methoxy-2-oxoethoxy)benzoate, C12H14O6
  8. The crystal structure of bis[(4-methoxyphenyl)(picolinoyl)amido-κ2 N:N′]copper(II), C26H22CuN4O4
  9. The crystal structure of poly[di(μ2-aqua)-diaqua-bis(3-aminopyridine-4-carboxylate-κ2 O: O′)-tetra(μ2-3-aminopyridine-4-carboxylate-κ2 O: O′)-dineodymium(III), [Nd2(C6H5N2O2)6(H2O)4] n
  10. The crystal structure of t-butyl 7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate, C28H34FNO4
  11. Crystal structure of catena-poly[(benzylamine-κ1 N)-(sorbato-κ1 O)-(μ2-sorbato-κ2 O,O′)-copper(II), C19H23CuNO4
  12. Crystal structure of (4-(2-chlorophenyl)-1H-pyrrol-3-yl)(ferrocenyl) methanone, C21H16ClFeNO
  13. The crystal structure of N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-3-(2-methylphenyl)-2-sulfanylprop-2-enamide hydrate, C19H17BrN2O2S2
  14. The crystal structure of N′-{5-[2-(2,6-dimethylphenoxy) acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl}-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide hydrate
  15. Crystal structure of 2-(naphthalen-1-yl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C26H24O3
  16. Crystal structure of naphthalen-1-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C25H22O3
  17. Crystal structure of poly[diaqua- (μ4-5-(1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ5N:O,O’:O’’:O’’’)calcium(II), C10H9CaN3O6
  18. Crystal structure of (E)-N′-(4-((E)-3-(dimethylamino)acryloyl)-3-hydroxyphenyl)-N, N-dimethylformimidamide, C14H19N3O2
  19. Crystal structure of (E)-3-(dimethylamino)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one, C13H17NO4
  20. Crystal structure of (2-chloropyridin-3-yl)methyl-2-(6-methoxynaphthalen-2-yl)propanoate, C20H18ClNO3
  21. The crystal structure of diethyl 4-(3,4-dimethylphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, C21H27NO4
  22. Crystal structure of (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-17-((4-(2-phenylpropyl)phenyl)ethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H42O2
  23. Synthesis and crystal structure of 4-(4-cyclopropylnaphthalen-1-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione, C15H13N3S
  24. Crystal structure of catena-poly[aqua-(2,6-di-(2-pyridyl)-pyridine-κ3 N,N′, N″)(μ2-1,4-naphthalene dicarboxylato-κ2 O,O′)nickel(II)], C27H19NiN3O5
  25. Crystal structure of 3-(diphenylphosphoryl)-3-hydroxy-1-phenylpropan-1-one, C21H19O3P
  26. The crystal structure of R,S-{N-[(2-oxidonaphthalen-1-yl)methylidene]phenylglycinato}divinylsilicon, C23H19NO3Si
  27. The crystal structure of 1,2,4-tris(bromomethyl)benzene, C9H9Br3
  28. Crystal structure of chlorido-[4-(pyridin-2-yl)benzaldehyde-κ2 N,C]-(diethylamine-κ1 N)platinum(II), C16H18ClN2OPt
  29. Crystal structure of 3-(methoxycarbonyl)-1-(4-methoxyphenyl)-2,3,4,9- tetrahydro-1H-pyrido[3,4-b]indol-2-ium chloride hydrate, C40H48Cl2N4O9
  30. The crystal structure of 1-(2-chlorobenzyl)-3-(3-chlorophenyl)urea, C14H12Cl2N2O
  31. Hydrothermal synthesis and crystal structure of aqua-tris(4-acetamidobenzoato-κ2 O,O′)-(1,10-phenanthroline-κ2 N,N′)terbium(III) hydrate C39H36N5O11Tb
  32. The crystal structure of zwitterionic 3-aminoisonicotinic acid, C6H6N2O2
  33. The crystal structure of bis{[monoaqua-μ2-4-[(pyridine-4-carbonyl)-amino]-phthalato-κ3 N:O,O′-(2,2′-bipyridine κ2 N,N′)copper(II)]}decahydrate, C48H56N8O22Cu2
  34. Crystal structure of poly[μ10-4,4′-methylene-bis(oxy)benzoatodipotassium], C15H10K2O6
  35. The crystal structure of catena-poly[[tetraaqua[(μ2-1,4-di(4-methyl-1-imidazolyl)benzene] cobalt(II)]bis(formate)], C16H24CoN4O8
  36. The crystal structure of (E)-2-chloro-5-((2-(nitromethylene)imidazolidin-1-yl)methyl)pyridine, C10H11ClN4O2
  37. The crystal structure of (E)-1-(((2-amino-4,5-dimethylphenyl)iminio)methyl)naphthalen-2-olate, C19H18N2O
  38. Crystal structure of N-(acridin-9-yl)-2-(4-methylpiperidin-1-yl) acetamide monohydrate, C21H25N3O2
  39. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2 O,O′)-zinc(II), C14H20Cl2N4O4Zn
  40. The crystal structure of 2,8-diethyl-1,3,7,9-tetramethyl-4λ4,5λ4-spiro[dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine-5,2′-naphtho[1,8-de][1,3,2]dioxaborinine], C25H29BN2O2
  41. The crystal structure of 5-tert-butyl-2-(5-tert-butyl-3-iodo-benzofuran-2-yl)-3-iodobenzofuran, C24H24I2O2
  42. Synthesis and crystal structure of methyl 2-{[4-(4-cyclopropyl-1-naphthyl)-4H-1,2,4-triazole-3-yl]thio} acetate, C18H17N3O2S
  43. The crystal structure of n-propylammonium bis(2,3-dimethylbutane-2,3-diolato)borate-boric acid (1/1), [C3H10N][C12H24BO4]·B(OH)3
  44. Crystal structure of methyl 1-(2-bromophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate, C19H17BrN2O2
  45. Crystal structure of (4-bromobenzyl)triphenylphosphonium bromide ethanol solvate, C52H48Br4OP2
  46. The crystal structure of unsymmetrical BOPHY C26H27BN4
  47. The crystal structure of Tb3B5O11(OH)2
  48. The crystal structure of (Z)-4-ethyl-2-((4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3,5-dimethyl-2H-pyrrol-1-ium 2,2'-spirobi[naphtho[1,8-de][1,3,2]dioxaborinin]-2-uide, C37H37BN2O4
  49. Crystal structure of bis(methylammonium) hexadecaselenidopalladate(II), (CH3NH3)2PdSe16
  50. The crystal structure of (2-diphenylphosphanylphenyl) 2-[7-(dimethylamino)-2-oxochromen-4-yl]acetate, C31H26NO4P
  51. Crystal structure of (E)-6-(4-ethylpiperazin-1-yl)-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C23H25FN2O
  52. The structure of RUB-56, (C6H16N)8 [Si32O64(OH)8]·32 H2O, a hydrous layer silicate (2D-zeolite) that contains microporous levyne-type silicate layers
  53. Crystal structure of 4-amino-3,5-dibromobenzonitrile, C7H4Br2N2
  54. Crystal structure of 2-(naphthalen-1-yl)ethyl 2-acetoxybenzoate, C21H18O4
  55. Single-crystal structure determination of Tm3B12O19(OH)7
  56. Crystal structure determination of NdB3.6O7
  57. The crystal structure of NdB6O8(OH)5·H3BO3
  58. Crystal structure of 2-(5-ethylpyridin-2-yl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H25NO3
  59. Crystal structure of N-(1-(3,4-dimethoxyphenyl)-2-methylpropyl)aniline, C18H23NO2
  60. Crystal structure of Ba6Cd12Mn4SiF48
  61. Synthesis and crystal structure of 5-fluoro-1-methyl-2-oxo-3-(2-oxochroman-4-yl)indolin-3-yl acetate, C20H16FNO5
  62. The crystal structure of 6-methacryloylbenzo[d][1,3]dioxol-5-yl 4-nitrobenzenesulfonate, C17H13NO8S
  63. Crystal structure of ethyl 2-(3-benzyl-4-oxo-3,4-dihydrophthalazin-1-yl)- 2,2-difluoroacetate, C19H16F2N2O3
  64. The crystal structure of tetrakis(μ 2-(1H-benzimidazole-2-methoxo-κ2 N,O:O:O)-(n-butanol-κO)-chlorido)-tetranickel(II), C48H68Cl4N8O8Ni4
  65. Synthesis and crystal structure of trans-tetraaqua-bis((1-((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carbonyl)oxy-κO)zinc(II)hexahydrate, C46H64N2O28S2Zn
  66. The crystal structure of 1-(4-carboxybutyl)-3-methyl-1H-imidazol-3-ium hexafluoridophosphate, C9H15F6N2O2P
  67. Crystal structure of 1-(4-chlorophenyl)-4-(2-furoyl)-3-phenyl-1H-pyrazol-5-ol, C20H13ClN2O3
  68. Crystal structure of dimethyl (R)-2-(3-(1-phenylethyl)thioureido)-[1,1′-biphenyl]-4,4′-dicarboxylate, C25H24N2O4S
  69. The crystal structure of 1-(3-carboxypropyl)-1H-imidazole-3-oxide, C7H10N2O3
  70. Synthesis and crystal structure of dimethyl 4,4′-(propane-1,3-diylbis(oxy))dibenzoate, C19H20O6
  71. Crystal structure of methyl-1-(p-tolyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate, C20H20N2O2
  72. The crystal structure of 1-(1-adamantan-1-yl)ethyl-3-(3-methoxyphenyl)thiourea, C20H28N2OS
  73. The crystal structure of N,N′-carbonylbis(2,6-difluorobenzamide), C15H8F4N2O3
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