Startseite The crystal structure of 2-hydroxy-4-((2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy)-3,6-dimethylbenzoic acid–methanol (1/1), C20H24O8
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The crystal structure of 2-hydroxy-4-((2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy)-3,6-dimethylbenzoic acid–methanol (1/1), C20H24O8

  • Fei Chen , Tianqiong Lang , Guoyong Luo und Wude Yang EMAIL logo
Veröffentlicht/Copyright: 31. Juli 2018

Abstract

C20H24O8, triclinic, P1̄ (no. 2), a = 4.6850(6) Å, b = 7.1895(2) Å, c = 29.1839(3) Å, α = 88.815(8)°, β = 86.346(8)°, γ = 80.052(9), V = 966.20(13) Å3, Z = 2, Rgt(F) = 0.0785, wRref(F2) = 0.2235, T = 205 K.

CCDC no.: 1832659

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.18 × 0.15 × 0.11 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:7616, 3587, 0.078
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1596
N(param)refined:263
Programs:Bruker [1], SHELX [2, 3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.9038(7)0.8925(4)0.94691(10)0.0460(9)
O21.1163(7)0.3271(4)0.86746(10)0.0430(9)
H21.04950.26700.84790.065*
O30.8414(7)0.2826(4)0.79688(10)0.0403(8)
O40.6109(7)0.5386(4)0.76159(9)0.0353(8)
O50.7767(8)0.4603(5)0.60299(10)0.0487(10)
H50.74270.39700.58120.073*
O60.5562(9)0.2145(5)0.56293(11)0.0610(11)
O70.3368(10)0.0108(5)0.60275(11)0.0657(12)
H70.3084−0.02120.57650.099*
C10.7421(12)1.0794(6)0.95271(16)0.0519(15)
H1A0.79061.15850.92700.078*
H1B0.79021.13150.98110.078*
H1C0.53601.07500.95400.078*
C20.8582(10)0.7945(6)0.90992(14)0.0340(11)
C31.0129(10)0.6120(6)0.90621(14)0.0331(11)
C40.9642(9)0.5068(6)0.86952(14)0.0297(10)
C50.7704(9)0.5777(6)0.83570(13)0.0281(10)
C60.6166(10)0.7642(6)0.83967(14)0.0317(11)
C70.6596(10)0.8688(6)0.87702(14)0.0357(11)
H7A0.55450.99190.88060.043*
C80.4013(11)0.8605(6)0.80708(15)0.0409(12)
H8A0.50260.88750.77830.061*
H8B0.29890.97760.82040.061*
H8C0.26330.77860.80140.061*
C91.2282(11)0.5307(7)0.94092(15)0.0442(13)
H9A1.15760.42840.95780.066*
H9B1.25090.62860.96210.066*
H9C1.41410.48310.92510.066*
C100.7440(9)0.4511(7)0.79800(13)0.0285(10)
C110.5839(9)0.4348(6)0.72212(14)0.0303(11)
C120.4198(9)0.2926(6)0.72561(13)0.0280(10)
H120.34040.26050.75450.034*
C130.3709(9)0.1967(6)0.68699(14)0.0282(10)
C140.1888(10)0.0438(6)0.69364(14)0.0328(11)
H14A0.02990.06740.67340.049*
H14B0.11140.04320.72530.049*
H14C0.3077−0.07770.68660.049*
C150.4918(9)0.2523(6)0.64355(13)0.0275(10)
C160.6542(9)0.3988(6)0.64224(14)0.0313(11)
C170.7019(9)0.4947(6)0.68148(14)0.0302(10)
C180.8738(10)0.6519(6)0.67723(15)0.0394(12)
H18A0.87300.71010.70690.059*
H18B0.78780.74550.65540.059*
H18C1.07210.60210.66660.059*
C190.4629(11)0.1581(7)0.60026(15)0.0417(13)
O80.2902(11)0.8494(7)0.52745(12)0.0875(16)
H80.34140.85680.49980.131*
C200.1197(16)0.7091(10)0.5339(2)0.095(3)
H20A−0.05030.74010.51610.143*
H20B0.05920.70080.56620.143*
H20C0.23140.58890.52390.143*

Source of material

The whole plants of Pyrrosia petiolosa (Christ) Ching were collected in March 2017 at Longli County, Guizhou Province, China. The air-dried plants (20 kg) were crushed and extracted with 95% EtOH at room temperature. The solvent was removed under reduced pressure to obtain the residue (2 kg), which was then suspended in 2 L of water, and extracted successively with petroleum ether, dichloromethane, ethyl acetate, and n-butanol. The petroleum ether fraction (35 g) was subjected to silica gel chromatography repeatedly to yield the title compound. The data used in this study was collected from its colorless block-shaped crystal in EtOAc/MeOH (1:1).

Experimental details

The software APEX 2 [1] was employed for data collection at 205 K. Using Olex2 [2], the structure was solved with the ShelXT [3] structure solution program using Intrinsic Phasing. Its structure was refined with the ShelXL refinement package [4]. Hydrogen atoms were positioned geometrically, with C—H distance of 0.94 Å for aromatic CH, 0.97 Å for CH3, and 0.83 Å for OH. The Uiso values were fixed at 1.2 times of all the C(H) group, and 1.5 times of CH3 and OH groups.

Comment

The title compound, with trivial names: barbatic acid or barbatinic acid, belongs to depside derivatives, the natural products commonly present in lichen [4], [5], [6], [7]. Depside derivatives have been reported to exhibit various biological effects including antimicrobial, anti-hepatic fibrosis, anti-diabetic, and antiviral activities [8], [9], [10]. Some crystal structures of depside derivatives have been reported before [10], [11], [12]. The bond lengths and angles of the title compound are in normal ranges. The methoxy group at C2 is almost coplaner with the benzene ring (C2, C3, C4, C5, C6, C7) with the torsion angle of 1.8(2)°, defined as plane I. The carboxyl group at C15 is twisted from the other benzene ring (C11, C12, C13, C15, C16 and C17) by 5.3(4)°, defined as plane II. The ester group is defined as plane III. For the steric interaction with the adjacent groups, plane III deviates from plane I with a dihedral angle of 13.9(3)°. In addition to two intramolecular hydrogen bonds, intermolecular hydrogen bonds are observed, which link the molecules of the compound into chains. Moreover, p-p interactions are observed with distances of 3.636 Å and 3.453 Å, respectively.

Acknowledgements

This work was supported by National Natural Science Foundation of China (81660647) and science and technology fund of Guizhou (QKHJ[2015]2019). The authors are also grateful to professor Qingwen Sun in the same University for his contribution to the voucher specimen identification of Pyrrosia petiolosa (Christ) Ching.

References

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Received: 2018-05-17
Accepted: 2018-07-16
Published Online: 2018-07-31
Published in Print: 2018-11-27

©2018 Fei Chen et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of di-μ2-aqua-tetraaqua-bis(4-(1H-1,2,4-triazol-1-yl)benzoato-κN)disodium(I) C18H24N6Na2O10
  3. Crystal structure of diaqua-bis(2-bromo-4-chloro-6-formylphenolato-κ2O,O′)cobalt(II), C16H16Cl2CrN3O7
  4. Crystal structure of catena-poly[(μ2-1-(4-(1H-pyrazol-1-yl)phenyl)ethan-1-one-κ2N:O)-bis(1,1,1-trifluoro-4-oxo-4-(thiophen-2-yl)but-2-en-2-olato-κ2O,O′)copper(II)], C27H18CuF6N2O5S2
  5. Crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C18H15F2NO5
  6. Crystal structure of 5,5′-dimethoxy-2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]diphenol, C20H24N2O6
  7. Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H14Cl2N2O2
  8. Crystal structure of 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine - trichloromethane (1/2), C98H84Cl6N8O8
  9. Crystal structure of methyl 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate, C24H21N3O5
  10. Crystal structure of catena-poly[(μ2-3,3′-thiodipropionato-κ2O:O′)-(bipyridine-κ2N,N′)copper(II)] C16H16CuN2O4S
  11. Crystal structure of [4-chloro-2-(((2-((3-ethoxy-2-oxidobenzylidene)amino)phenyl)imino)(phenyl)methyl)phenolato-κ4N,N′,O,O′}nickel(II) - ethyl acetate (1/1), C32H29ClN2NiO5
  12. Crystal structure of (4-(4-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C29H52Cl2N4NiO9
  13. Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C20H21NO5
  14. Structure and photochromism of 1,2-bis[2-methyl-5-(3-quinolyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C33H20F6N2S2
  15. Crystal structure of catena-poly[diaqua-bis(μ2-3,5-di(1H-1,2,4-triazol-1-yl)benzoate-κ2N:N′)cobalt(II))] 2.5 hydrate, C22H23CoN12O8.50
  16. The crystal structure of dichlorido(1,3-dimesityl-1H-3λ4-imidazol-2-yl)(morpholine-κN)palladium(IV), C25H33Cl2N3OPd
  17. Crystal structure of catena-poly[bis(4,4′-dipyridylaminium-kN)-(μ2-germanowolframato-κ2O:O′)-(2,2′-bipyridine-κ2N,N′)copper(II)] with a Keggin-type heteropolyoxoanion, [Cu(C10H8N2)(C10H10N3)2][GeW12O40] ⋅ H2O
  18. Crystal structure of diaqua-(N-(1-(pyrazin-2-yl)ethylidene)pyridin-1-ium-4-carbohydrazonate-κ3N,N′,O)-tris[nitrato-κ2O,O′)lanthanum(III), C12H15N8O12La
  19. The crystal structure of 2-hydroxy-4-((2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy)-3,6-dimethylbenzoic acid–methanol (1/1), C20H24O8
  20. Crystal structure of guanidinium tetrapropylammonium bis(hydrogencarbonate) dihydrate, C15H40N4O8
  21. Crystal structure of (Z)-2-bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one, C23H27BrO2
  22. Crystal structure of 2-(4-(4H-1,2,4-triazol-4-yl)phenyl)acetic acid, C10H9N3O4
  23. Crystal structure of 4,4′-(1,4-phenylene)bis(1H-imidazol-3-ium)bis(2-carboxybenzoate), C30H26N4O8
  24. Crystal structure of 4,4′-(4,10-diphenyl-4,10-dihydropyreno[4,5-d:9,10-d′]diimidazole-5,11-diyl)bis(N,N-diphenylaniline), C66H44N6
  25. Crystal structure of catena-poly[diaqua-bis(μ2-5-(3-(1H-imidazol-5-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)], C20H18CoN12O2
  26. Crystal structure of 1,3-dimethyl-2-(p-tolyl)-1H-perimidin-3-ium iodide 1.5 hydrate, C20H22IN2O1.5
  27. Crystal structure of 2-(4-methoxyphenyl)chromane, C16H16O2
  28. Crystal structure of poly[(μ2-2-carboxy-5-nitroisophthalato-κ2O:O′)-(μ2-4-((1H-imidazol-1-yl)methyl)pyridine-κ2N:N′)zinc(II)], C18H12N4O8Zn
  29. Crystal structure of bis(1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)tetraiodidodicadmium(II), [Cd2(C13H15N5)2I4]
  30. Crystal structure of tetramethylammonium bis(acetato-κ1O)-tetrakis(μ3-3-((hydroxyimino)methyl)-5-methoxy-2-oxidobenzoate-κ5O,O′:O′,N:O′′)tetrazinc(II) — N,N′-dimethylformamide — water (1/2/2), C62H96Zn4N10O28
  31. Crystal structure of poly[(μ4-5-tert-butylisophthalato-κ4O:O′:O′′:O′′′)-(1,3-dimethyl-2-imidazolidinone-κO)zinc(II)] C17H22N2O5Zn
  32. Crystal structure of [tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′]-[(pyridine-2,6-dicarboxylato-κ2O,N)]cadmium(II)–methanol (1:3) C34H36CdN8O7
  33. The crystal structure of bis(1H-benzo[d]imidazol-2-amine-κN)-diiodidocadmium(II), C14H14CdI2N6
  34. Crystal structure of tetrakis(1H-benzimidazol-2-amine)-κN)-bis(μ2-sulfonato-κ2O:O′)dizinc(II) - methanol (1/1), C30H36N12O10S2Zn2
  35. Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO
  36. Crystal structure of dimethyl 4,4′-oxydibenzoate, C16H14O5
  37. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-3-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)zinc(II)], C17H16I2N4OZn
  38. Crystal structure of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile, C26H18F2N2O3S
  39. Crystal structure of bis(acetato-κ1O)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)zinc(II), C18H22N4O6Zn
  40. The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
  41. Crystal stucture of 2-(tert-butyl)-6-(hydroxymethyl)-4-methylphenol, C12H18O2
  42. Crystal structure of catena-poly[(2-(5-chloroquinolin-8-yloxy)-1-(pyrrolidin-1-yl)ethan-1-one-κ3N,O,O′)-(dinitrato-κ2O,O′)mercury(II)], C15H15N4O8ClHg
  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
  44. The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
  45. Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
  46. The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
  47. Crystal structure of 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
  48. Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S
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