Home Synthesis and crystal structure of (S,E)-4-hydroxy-3-(2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)dihydrofuran-2(3H)-one, C23H34O5
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Synthesis and crystal structure of (S,E)-4-hydroxy-3-(2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)dihydrofuran-2(3H)-one, C23H34O5

  • Shi-Qing Li ORCID logo , Jian Zhou , Zhang-Chao Dong , Bo Wen Pan , Yang Shi EMAIL logo and Ying Zhou EMAIL logo
Published/Copyright: June 1, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 4

Abstract

C23H34O5, orthorhombic, P212121 (no. 19), a = 11.1838(3) Å, b = 11.7824(3) Å, c = 16.3160(5) Å, V = 2149.99(10) Å3, Z = 4, R g t (F) = 0.0399, w R r e f (F 2) = 0.1097, T = 293 K.

CCDC no.: 2254956

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: Colourless block
Size: 0.14 × 0.12 × 0.11 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 0.67 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 73.9°, >99%
N(hkl)measured, N(hkl)unique, R int: 8110, 4232, 0.025
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3679
N(param)refined: 266
Programs: CrysAlis PRO [1], Olex2 [2], Shelx [3]
Table 2:

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

Atom x y z U iso*/U eq
O1 0.18819 (17) 0.59727 (18) 0.50066 (12) 0.0619 (5)
O2 0.34093 (16) 0.48648 (15) 0.44532 (11) 0.0528 (4)
O3 0.8734 (3) 0.21889 (18) 0.7631 (2) 0.1146 (12)
H3 0.862456 0.149198 0.770993 0.172*
O4 1.14370 (19) 0.29991 (16) 0.72856 (14) 0.0678 (6)
O5 1.12454 (19) 0.48536 (16) 0.71378 (14) 0.0666 (5)
C1 0.3919 (2) 0.65135 (19) 0.52992 (15) 0.0455 (5)
C2 0.2728 (2) 0.6107 (2) 0.56600 (17) 0.0537 (6)
H2A 0.284310 0.537431 0.594655 0.064*
H2B 0.242667 0.666830 0.606141 0.064*
C3 0.4051 (2) 0.5924 (2) 0.44584 (15) 0.0487 (6)
H3A 0.370981 0.643034 0.402560 0.058*
C4 0.5335 (2) 0.5688 (2) 0.42584 (16) 0.0535 (6)
H4A 0.577276 0.641747 0.423400 0.064*
H4B 0.537755 0.533627 0.370809 0.064*
C5 0.5961 (2) 0.4908 (2) 0.48740 (15) 0.0509 (6)
H5A 0.683545 0.501057 0.481656 0.061*
H5B 0.577564 0.411113 0.472834 0.061*
C6 0.5619 (2) 0.50988 (18) 0.57861 (14) 0.0401 (5)
C7 0.5006 (2) 0.62818 (17) 0.58752 (15) 0.0413 (5)
H7 0.562891 0.684578 0.570861 0.050*
C8 0.4722 (2) 0.6559 (2) 0.67701 (16) 0.0514 (6)
H8A 0.435744 0.732307 0.680258 0.062*
H8B 0.413328 0.600375 0.698190 0.062*
C9 0.5845 (3) 0.6526 (2) 0.73036 (18) 0.0576 (7)
H9A 0.637532 0.716561 0.715312 0.069*
H9B 0.561684 0.661796 0.788597 0.069*
C10 0.6511 (2) 0.5425 (2) 0.71985 (15) 0.0469 (6)
C11 0.6781 (2) 0.51401 (18) 0.63154 (14) 0.0424 (5)
H11 0.725091 0.579767 0.610022 0.051*
C12 0.7600 (2) 0.4100 (2) 0.62167 (18) 0.0527 (6)
H12A 0.726785 0.345966 0.653742 0.063*
H12B 0.761488 0.387022 0.563307 0.063*
C13 0.8845 (2) 0.43309 (19) 0.64961 (15) 0.0469 (5)
H13 0.911699 0.509174 0.644581 0.056*
C14 0.9612 (2) 0.35955 (19) 0.68054 (14) 0.0425 (5)
C15 0.9476 (3) 0.2341 (2) 0.69551 (18) 0.0532 (6)
H15 0.914420 0.195072 0.646079 0.064*
C16 1.0753 (3) 0.1998 (3) 0.7104 (3) 0.0889 (13)
H16A 1.079593 0.146010 0.756851 0.107*
H16B 1.108022 0.161897 0.661088 0.107*
C17 1.0814 (2) 0.3925 (2) 0.70781 (15) 0.0472 (6)
C18 0.2140 (2) 0.5019 (3) 0.45048 (17) 0.0603 (7)
C19 0.1605 (3) 0.5272 (4) 0.3672 (2) 0.0842 (11)
H19A 0.199790 0.594024 0.343618 0.126*
H19B 0.074744 0.542166 0.373134 0.126*
H19C 0.172359 0.461885 0.330914 0.126*
C20 0.1664 (4) 0.3932 (3) 0.4883 (3) 0.0839 (10)
H20A 0.189874 0.328359 0.454273 0.126*
H20B 0.079029 0.396994 0.491570 0.126*
H20C 0.199667 0.384040 0.543484 0.126*
C21 0.3847 (3) 0.7798 (2) 0.5146 (2) 0.0659 (8)
H21A 0.384082 0.819940 0.567138 0.099*
H21B 0.311204 0.797247 0.484335 0.099*
H21C 0.454091 0.804028 0.482371 0.099*
C22 0.4842 (2) 0.41017 (19) 0.60855 (17) 0.0504 (6)
H22A 0.457706 0.424817 0.664817 0.076*
H22B 0.531172 0.339984 0.607097 0.076*
H22C 0.414299 0.402301 0.572780 0.076*
C23 0.6814 (3) 0.4788 (3) 0.78361 (19) 0.0614 (7)
H23A 0.665 (3) 0.515 (3) 0.842 (2) 0.074 (10)*
H23B 0.731 (3) 0.407 (3) 0.779 (2) 0.074 (10)*

1 Source of material

Andrographolide (40 g, 114 mmol) was dissolved in a mixed solution of toluene (400 mL) and dimethyl sulfoxide (64 mL), and 4-toluenesulfonic acid (2 g, 11.6 mmol) and 2,2-dimethoxypropane (48 mL, 544 mmol) were added separately with stirring and heated to 90 °C for 4 h. Upon completion, the mixture was filtered through celite, and washed with CH2Cl2 (10 mL) and concentrated in vacuo. Then, the crude product was subjected to flash column chromatography on silica gel (petroleum ether/ethyl acetate = 1:1) to afford the product.

2 Experimental details

The carbon-bound hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms with d(C–H) = 0.82–1.06(4) Å, U iso(H) = 1.5 times U eq(C) and 1.2 times U eq(O).

3 Comment

Andrographolide, a diterpenoid lactone [4], can be obtained from the extract of traditional herb paniculata with extraordinary efficacy. Andrographolide and its derivatives are important bioactive compounds. They have good potential for applications in fields of pharmacology [5], [6], [7]. Therefore, the synthesis and modification of Andrographolide have always been a hot topic in the medical field.

The title compound contains one diterpenoid lactone, three hydroxyl, one oxygen-containing pentacyclic, and four methyl groups. The bond lengths and angles derived from the title structure are within normal ranges and consistent with those reported previously in similar structures [8–10]. The C=C bond was determined at the distance of 1.320(3) Å (C13–C14). The carbonyl group was confirmed by the distance of 1.200(3) Å (C17–O5), and the alcohol hydroxyl group was identified by the distance of 1.393(4) Å (C15–O3), respectively. The oxygen-containing pentacycle with C17–O4–C16 torsion angle of 109.9 ( 2 ) ∘ . The oxygen-containing pentacycle was confirmed by the distance of 1.337(3) Å (C17–O4), distance and of 1.436(4) Å (C16–O4), respectively.

Corresponding authors: Yang Shi and Ying Zhou, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, P.R. China, E-mail: ,

Funding source: Guizhou Graduate Research Fund Project

Award Identifier / Grant number: YJSKYJJ[2021]165

Funding source: Key Disciplines of Traditional Chinese Medicine and Ethnic Medicine in Guizhou Province

Award Identifier / Grant number: QZYYZDXK(JS)-2021-03

Funding source: Guizhou province

Award Identifier / Grant number: gzwkj2022-232 and gzwkj2022-467

Funding source: Guizhou Provincial Science and Technology Projects

Award Identifier / Grant number: 404

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

  2. Research funding: Guizhou Provincial Science and Technology Projects (Qian Ke He Zi ZK [2023] general 404 ), 2021 Guizhou Graduate Research Fund Project (Qian Jiao He YJSKYJJ[2021]165), Key Disciplines of Traditional Chinese Medicine and Ethnic Medicine in Guizhou Province during the 14th Five-Year Plan (QZYYZDXK(JS)-2021-03) and the projects of Guizhou province (Qian Jiao He KY Zi [2022]253, gzwkj2022-232 and gzwkj2022-467).

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

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Received: 2023-04-12
Accepted: 2023-05-18
Published Online: 2023-06-01
Published in Print: 2023-08-28

© 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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https://doi.org/10.1515/ncrs-2023-0179
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of a polymorph of potassium picrate, C6H2KN3O7
  4. The crystal structure of (1E,2E)-1,2-bis(quinolin-2-ylmethylene)hydrazine, C20H14N4
  5. 5-Amino-2-chloro-4-fluoro-N-(N-isopropyl-N-methylsulfamoyl) benzamide, C11H15O3ClFN3S
  6. Crystal structure of trans-N 1,N 8-bis(2-cyanoethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H42N6
  7. The crystal structure of [N-{[2-(oxy)-4-methoxyphenyl](phenyl)methylidene}alaninato]-diphenyl-silicon(IV) – chloroform (1/1), C29H25NO4Si·CHCl3
  8. Crystal structure of tetracarbonyl-{μ-[N-(diphenylphosphanyl)-N,P,P-triphenylphosphinous amide]}-bis[μ-(phenylmethanethiolato)]diiron (Fe–Fe), C48H39Fe2NO4P2S2
  9. Crystal structure of baryte from Mine du Pradet (France)
  10. The crystal structure of [(2,2′-bipyridine-6-carboxylato-κ3 N,N,O)-(6-phenylpyridine-2-carboxylate-κ2 N,O)copper(II)] monohydrate, C23H17N3O5Cu
  11. Crystal structure of bis(μ-benzeneselenolato)-(μ-[N-benzyl-N-(diphenylphosphanyl)-P,P-diphenylphosphinous amide])-tetracarbonyl diiron (Fe–Fe), C47H37Fe2NO4P2Se2
  12. The crystal structure of diaqua-methanol-κ1 O- (3-thiophenecarboxylato-κO)-(2,2′-dipyridyl-κ2 N,N′)manganese(II) 3-thiophenecarboxylate, C21H22N2O7S2Mn
  13. Crystal structure of catena-poly[tetrakis(butyl)-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O:O,O′,N-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O,N,O′:N′-ditin(IV)], C34H50N6O6Sn2
  14. Crystal structure of 4-chloro-N′-[(1E)-(2-nitrophenyl)methylidene]benzohydrazide, C14H10ClN3O3
  15. The crystal structure of 3-(1′-deoxy-3′,5′-O-dibenzy-β-d-ribosyl)adenine dichloromethane solvate, C49H52Cl2N10O6
  16. The crystal structure of (Z)-4-amino-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H17N3O
  17. The co-crystal structure of etoricoxib–phthalic acid (1/1), C18H15ClN2O2S·C8H6O4
  18. Crystal structure of (glycinto-κ 2 O,N ′)-[5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ 4 N,N ′,N ″,N ‴]nickel(II) perchlorate monohydrate C18H42ClN5NiO7
  19. The crystal structure of catena-poly[bis(1-ethylimidazole-k1 N)-(μ 2-benzene-1-carboxyl-3,5-dicarboxylato-κ 2 O, O′)zinc(II)], C19H20N4O6Zn
  20. Crystal structure of 3-(thiazol-2-ylcarbamoyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid, C11H12N2O4S
  21. Rietveld structure analysis of keatite, a rare, metastable SiO2 polymorph
  22. Crystal structure of catena-poly[(μ2-isophthalato-k3 O,O′:O″)(4-(4-pyridyl)-2,5-dipyrazylpyridine-k3 N,N′,N″)cobalt(II)] trihydrate C26H22N6O7Co1
  23. Crystal structure of 3,5–di-O-benzoyl-1,2-O-isopropylidene-α–D-ribose, C22H22O7
  24. The crystal structure of fac-tricarbonyl(6-bromo-2,2-bipyridine-κ2 N,N)-(nitrato-κO)rhenium(I), C13H7BrN3O6Re
  25. The crystal structure of (E)-N′-(4-hydroxy-3-methoxybenzylidene)-2-naphthohydrazide monohydrate, C19H18N2O4
  26. The crystal structure of 5,5′-diselanediyl-bis(2-hydroxybenzaldehyde), C14H10O4Se2
  27. The crystal structure of catena-poly[diaqua-m2-dicyanido-κ2 C:N-dicyanido-κ1 C-bis(4-(pyridin-4-yl)benzaldehyde-κ1N)iron(II)-platinum(II), C28H22N6O4PtFe
  28. Redetermination of the crystal structure of 5,14-dihydro-6,17-dimethyl-8,15-diphenyldibenzo(b,i)(1,4,8,11)tetra-azacyclotetradecine, C32H28N4
  29. Crystal structure of poly[(μ3-2-(3,5-dicarboxyphenyl) benzimidazole-6-carboxylato-κ4O:O:O′:O″)lead(II)] monohydrate, C16H10N2O7Pb
  30. The crystal structure of fac-tricarbonyl(2-pyridin-2-yl-quinoline-κ2 N,N′)-(pyrazole-κN)rhenium(I)nitrate, C20H14N4O3ReNO3
  31. Crystal structure of dibromo-dicarbonyl-bis(tricyclohexylphosphine)-osmium(II) dichloromethane solvate, C38H66Br2O2OsP2
  32. Crystal structure of poly[bis(μ 2-2,6-bis(1-imidazoly)pyridine-κ 2 N:N′)copper(II)] diperchlorate dihydrate, C22H22Cl2CuN10O10
  33. The crystal structure of fac-tricarbonyl(N-benzoyl-N,N-cyclohexylmethylcarbamimidothioato-κ2 S,O)-(pyridine-κN)rhenium(I), C23H24N3O4ReS
  34. Crystal structure of (E)-7-fluoro-2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O
  35. Synthesis and crystal structure of 1-((3R,10S,13S, 17S)-3-((2-methoxyphenyl)amino)-10,13-dimethylhexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO2
  36. The crystal structure of fac-tricarbonyl((pyridin-2-yl)methanamino-κ2 N,N′)-((pyridin-2-yl)methanamino-κN)rhenium(I) nitrate, C15H16O3N4Re
  37. The crystal structure of (1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)-N-((1-(4-vinylbenzyl)-1H-benzo[d]imidazol-2-yl)methyl)methanamine-κ 4 N,N′,N″,N‴)tris(nitrato-kO,O′)-erbium(III), C29H27ErN8O9
  38. Crystal structure of tetracene-5,12-dione, C18H10O2
  39. Crystal structure of (3R,3aS,6R,6aR)-6-hexyl-3-methyltetrahydrofuro[3,4-b]furan-2,4-dione, C13H20O4
  40. The crystal structure of N′1,N′3-bis((E)-thiophen-2-ylmethylene)isophthalohydrazide monohydrate, C18H16N4O3S2
  41. Crystal structure of methyl ((4-aminobenzyl)sulfonyl)-L-prolinate, C13H18N2O4S
  42. Crystal structure of (E)-3-(3-methoxybenzylidene)benzofuran-2(3H)-one, C16H12O3
  43. Synthesis and crystal structure (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C11H12BrNO2
  44. Synthesis and crystal structure of (S,E)-4-hydroxy-3-(2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)dihydrofuran-2(3H)-one, C23H34O5
  45. The crystal structure of N,N′-(1,2-phenylene)bis (2-((2-oxopropyl)selanyl)benzamide), C26H24N2O4Se2
  46. The crystal structure of 1-ethyl-2-nitro-imidazole oxide, C5H7N3O3
  47. The crystal structure of 2-(2-fluorophenyl)naphtho[2,1-d]thiazole, C17H10FNS
  48. Crystal structure of (E)-2,4-di-tert-butyl-6-(((2-fluorophenyl)imino) methyl)phenol, C21H26FNO
  49. Synthesis and crystal structure of 3-methyl-2-(methylthio)-4H-chromen-4-one, C12H12O2S
  50. Crystal structure of dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-5,10-dione, C14H4O2S4
  51. The crystal structure of dimethyl 2,2ʹ-((adamantane-1,3-diylbis(4,1-phenylene)) bis(oxy))diacetate, C28H32O6
  52. The crystal structure of N-(6-chloro-2-methyl-2H-indazol-5-yl)acetamide, C10H10ClN3O
  53. Crystal structure of triaqua-(5-bromoisophthalato-κ1 O)-(2,2′-bipyridine-κ2 N:N′)nickel(II) hydrate, C18H19BrN2NiO8
  54. The crystal structure of 2-amino-4-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  55. The crystal structure of catena-poly[5-aminonicotinic acid-k1 N-m2-bromido-copper(I)], Cu(C6N2H6O2)Br
  56. The crystal structure of 2,2-bis(3-methoxyphenyl)-1-tosyl-1,2-dihydro- 2λ4,3λ4  -[1,3,2]diazaborolo[4,5,1-ij]quinoline - dichloromethane (1/1)
  57. The crystal structure of catena-poly[bis(6-phenylpyridine-2-carboxylato-κ2 N,O)-(μ2-4,4′-bipyridne-κ2 N:N)cadmium(II)], C34H24N4O4Cd
  58. The crystal structure of 5,7-dinitropyrazolo[5,1-b]quinazolin-9(4H)-one, C10H5N5O5
  59. Crystal structure of rac-1,8-bis(2-carbamoylethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H46N6O2
  60. The crystal structure of (E)-N ′-(2-bromobenzylidene)-2-naphthohydrazide, C36H26Br2N4O2
  61. The crystal structure of 5-nitronaphthoquinone, C10H5NO4
  62. The crystal structure of (S, R p )-4–benzhydrylideneamino-12-(4-tert-butyl oxazolin-2-yl)[2.2]paracyclophane, C36H36N2O
  63. Synthesis and crystal structure of 2-(2-oxo-2-(o-tolyl)ethyl)-4H-chromen-4-one, C18H14O3
  64. Crystal structure of 2-(thiazol-2-yl)hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione, C11H10N2O3S
  65. Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5
  66. Crystal structure of poly[(μ3-3, 5-dichloro-2-hydroxy-benzoato-κ4 Cl,O:O′:O″) silver(I)], C7H3AgCl2O3
  67. The crystal structure of tetrakis(1-isopropylimidazole-κ1 N)-[μ2- imidazole-4,5-dicarboxylato-κ4 O,N,O′,N′)]- trioxido-divanadium, C29H41N10O7V2
  68. Crystal structure of catena-[(μ3-bromido)-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N)copper(I)], C9H7BrCuN3O2
  69. The crystal structure of (E)-4-fluoro-N′-(1-(2-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
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