Startseite Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7
Artikel Open Access

Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7

  • Shu-jun Shan , Yao-yao Cao , Ping Yao , Pei-pei Du , Sai Chen EMAIL logo und Hong-lei Li ORCID logo EMAIL logo
Veröffentlicht/Copyright: 8. Januar 2025

Abstract

C22H22O7, monoclinic, P21/n (no. 14), a = 7.8761(5) b = 17.0563(11) Å, c = 14.0504(10) Å, β = 95.563(4)°, V = 1878.6(2) Å3, Z = 4, Rgt(F) = 0.0504, wRref(F2) = 0.1475, T = 296(2) K.

CCDC no.: 2302075

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: Orange needle
Size: 0.28 × 0.16 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.11 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 25.2°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 27,359, 3,379, 0.032
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2,895
N(param)refined: 262
Programs: Olex2, 1 , 2 SHELX 3 , 4
Table 2:

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

Atom x y z Uiso*/Ueq
C′ 0.9980 (4) 0.6155 (2) 0.9957 (2) 0.0858 (10)
H′A 1.047297 0.651414 1.043239 0.129*
H′B 0.989218 0.564510 1.023660 0.129*
H′C 1.069099 0.612608 0.944015 0.129*
C1 0.4512 (2) 0.58886 (11) 0.67536 (13) 0.0351 (4)
C1′ 0.6007 (2) 0.61573 (12) 0.83728 (13) 0.0416 (5)
H1′ 0.623467 0.666500 0.808417 0.050*
C2 0.5419 (2) 0.55900 (12) 0.75849 (13) 0.0373 (4)
C2′ 0.4650 (3) 0.62708 (13) 0.90612 (15) 0.0472 (5)
H2′A 0.434597 0.576548 0.931229 0.057*
H2′B 0.363478 0.649448 0.871953 0.057*
C3 0.5633 (2) 0.47830 (12) 0.76594 (13) 0.0401 (5)
C3′ 0.5279 (3) 0.68086 (14) 0.98869 (16) 0.0538 (6)
H3′A 0.538522 0.733988 0.965346 0.065*
H3′B 0.446172 0.681146 1.036088 0.065*
C4A 0.3950 (2) 0.45750 (11) 0.61627 (12) 0.0336 (4)
C4 0.4910 (2) 0.42805 (12) 0.69556 (14) 0.0408 (5)
H4 0.507332 0.374236 0.701933 0.049*
C4′ 0.6998 (3) 0.65245 (15) 1.03405 (15) 0.0568 (6)
H4′A 0.685641 0.602444 1.065196 0.068*
H4′B 0.744542 0.689674 1.082309 0.068*
C5 0.1290 (2) 0.38437 (11) 0.39539 (13) 0.0379 (4)
H5 0.142602 0.330695 0.404983 0.045*
C5′ 0.8260 (3) 0.64332 (16) 0.95887 (16) 0.0588 (6)
H5′ 0.837899 0.694157 0.927692 0.071*
C6 0.0295 (2) 0.41244 (11) 0.31630 (13) 0.0376 (4)
C7 0.0103 (2) 0.49244 (12) 0.30151 (13) 0.0394 (4)
H7 −0.056141 0.510589 0.247702 0.047*
C7′ −0.0202 (4) 0.65224 (14) 0.26944 (17) 0.0626 (7)
H7′A −0.021550 0.708506 0.270722 0.094*
H7′B 0.033403 0.634682 0.214736 0.094*
H7′C −0.135094 0.632850 0.265635 0.094*
C8A 0.1905 (2) 0.51850 (10) 0.44822 (12) 0.0316 (4)
C8 0.0888 (2) 0.54549 (11) 0.36576 (13) 0.0351 (4)
C8′ −0.0350 (3) 0.28468 (13) 0.25559 (17) 0.0585 (6)
H8′A −0.102603 0.259719 0.203655 0.088*
H8′B 0.083006 0.271843 0.252582 0.088*
H8′C −0.070863 0.266689 0.315215 0.088*
C9A 0.3751 (2) 0.53886 (10) 0.60356 (12) 0.0325 (4)
C9 0.2761 (2) 0.57199 (11) 0.51971 (12) 0.0340 (4)
C10A 0.2077 (2) 0.43694 (10) 0.45993 (12) 0.0325 (4)
C10 0.3128 (2) 0.40279 (11) 0.54431 (14) 0.0383 (4)
O1 0.4377 (2) 0.66714 (8) 0.66738 (10) 0.0502 (4)
H1 0.381202 0.678234 0.617060 0.075*
O2 0.6542 (2) 0.44459 (10) 0.84216 (10) 0.0599 (5)
H2 0.706939 0.478518 0.874100 0.090*
O3 0.3278 (2) 0.33212 (8) 0.55354 (12) 0.0627 (5)
O4 −0.0567 (2) 0.36715 (8) 0.24864 (10) 0.0514 (4)
O5 0.0723 (2) 0.62367 (8) 0.35400 (10) 0.0534 (4)
O6 0.2660 (2) 0.64438 (8) 0.51072 (10) 0.0533 (4)
O7 0.75589 (17) 0.58746 (10) 0.88715 (10) 0.0525 (4)

1 Source of material

The title compound is a natural product, which has been obtained by extraction and isolation from fungal fermentation products. 5 , 6

2 Experimental details

The structure was treated with the Olex2 crystallographic software package, 1 , 2 solved with the SHELXT structure solution program and refined with the SHELXL refinement package. 3 , 4 Carbon-bound hydrogen atoms were placed in calculated positions and refined with riding coordinates, with Uiso(H) fixed at 1.2 times of Ueq(C) (Tables 1 and 2).

3 Comment

The scaffold of 9,10-anthraquinone has attracted researchers’ interest due to its wide range of bio-activities, such as antitumor, antifungal, antidiabetic, anti-malarial, etc. 7 , 8 , 9 , 10 The title structure is composed of 9,10-anthraquinone and a pyranonyl group. The two moieties are not co-planar and have a C1⃛C2⃛C1′⃛C2′ torsion angle of 88.514°, which is different from previous reports. 11 The geometry of title structure was characterized with the bond angles and lengths. In particular, the bond angles for C7′⃛O5⃛C8, C8′⃛O4⃛C6, H1⃛O1⃛C1, H2⃛O2⃛C3, C1′⃛O7⃛C5′, C1′⃛C2′⃛O7′, O4⃛C6⃛C7 and O4⃛C6⃛C5 are 118.54(16)°, 117.91(16)°, 109.465°, 34.567°, 110.52(16)°, 114.58(16)° and 124.97(18)°, respectively. The bond lengths of C9⃛O6, C1⃛O1, C8⃛O5, C6⃛O4, C5⃛C10A, C10⃛O3, C1′⃛O7 and C12⃛C1′ are 1.243(2) Å, 1.343(2) Å, 1.348(2) Å, 1.355(2) Å, 1.379(3) Å, 1.217(2) Å, 1.432(2) Å and 1.509(3) Å, closely resembling to the reported ones. 12 Furthermore, there are two types of hydrogen bonds: O1⃛H1⃛O6, O2⃛H2⃛O7, with bond lengths of 1.768 Å and 1.903 Å, respectively. And it was further unequivocally secured that the stereo configurations of C1′ and C5′ are 1′ R and 5′ R. In the crystal structure, the three independent molecules form a trimer and the centroid-centroid distances of the π-π interactions are 3.493–3.594 Å, which is approximate to the reported. 13


Corresponding authors: Sai Chen and Hong-lei Li, Department of Pharmacy, Kangda College of Nanjing Medical University, Lianyungang 222000, People’s Republic of China, E-mail: (S. Chen), (H.-l. Li)

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

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

  3. Research funding: This work was supported by the Scientific Research Personnel Training Program of Kangda College of Nanjing Medical University (No.KD2022KYRC007), Science & Technology Funds of Kangda College of Nanjing Medical University (No.KD2023KYJJ017&KD2023KYJJ019), the Science & Technology Funds of Lianyungang (No. SF2107 & JCYJ2320), and Jiangsu Province Drug Administration scientific research program projects (202416).

References

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Received: 2024-11-13
Accepted: 2024-12-23
Published Online: 2025-01-08
Published in Print: 2025-04-28

© 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 N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2
  4. Synthesis and crystal structure of ethyl (2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR,E)-10-(((3,4-dichlorobenzyl)oxy)imino)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate
  5. The crystal structure of pyrazole nitrate
  6. Crystal structure of tetramethyl-bis(μ2-2-(2-hydroxy-3-methoxybenzylidene)-1-(6-(2-(2-hydroxy-3-methoxybenzylidene)hydrazine-1-carbonyl)picolinoyl)hydrazin-1-ido-κ4O,N,O′:O′)ditin(II) ─ ethanol (1/2), C54H62N10O14Sn2
  7. Crystal structure of catena-poly[μ3-iodido-(4-bromopyridine-κ1N)copper(I)], C5H4BrNCuI
  8. The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P
  9. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(phenylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C34H48N2O
  10. The crystal structure of (E)-3-((E)-3-(4-ethoxy-3-methoxyphenyl)-1-hydroxyallylidene) chroman-2,4-dione, C21H18O6
  11. The crystal structure of trans–L/D-[bis-(2-methyl-8-hydroxyquinoline-κ2 N,O) bis-(1,3,5-triaza-7-phosphaadamantane-κ2 P)cobalt(III)] tetrafluoroborate
  12. Crystal structure of 9-chloro-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C14H15ClN4
  13. Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3
  14. The crystal structure of 4–bromo-3,5-dinitropyrazole
  15. Crystal structure of 8-hydroxy-3,5,8a-trimethyl-7,8,8a,9-tetrahydronaphtho[2,3-b]furan-4,6-dione, C15H16O4
  16. Crystal structure of 5-hydroxy-3,5,8a-trimethyl-4a,5,6,7,8a,9-hexahydronaphtho[2,3-b]furan-4,8-dione, C15H18O4
  17. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(p-tolylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C35H50N2O
  18. The crystal structure of catena-poly((μ2-1,3,5-tri(1H- imidazol-1-yl)benzene κ2N:N′)-bis(4-hydroxbenzoato-κ1O)-zinc(II) monohydrate), C29H24N6O7Zn
  19. Crystal structure of 2-(benzo[d]oxazol-2-yl)acetonitrile, C9H6N2O
  20. Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7
  21. The crystal structure of the double salt potassium 1-methylpiperazine-1,4-di-ium trinitrate, C5H14KN5O9
  22. Crystal structure of 5′-hydroxy-6′-methoxy-1′-methyl-2′,3′,8′,8a′-tetrahydro-1′H-spiro[cyclohexane-1,7′-cyclopenta[ij]isoquinoline]-2,5-dien-4-one, C18H19NO3
  23. The crystal structure of 1,1′-(2,3,5,6-tetramethylpyrazine-1,4-diyl)bis(ethan-1-one), C12H18N2O2
  24. Crystal structure of [μ2-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ2O:O′)] bis(μ2-4,4′-trimethylenedipyridyl-κ2N:N′)disilver(I), C18H24AgN3O4S
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  27. The crystal structure of barium hexahydroxidoiridate(IV) dihydroxide, Ba2[Ir(OH)6](OH)2
  28. Crystal structure of cinnamoyl ferrocene, C19H16FeO
  29. Crystal structure of (E)-3-(4-butoxyphenyl)acryloylferrocene, C23H24FeO2
  30. Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
  31. The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5
  32. The crystal structure of 1,3,5-trichloro-2-nitrobenzene
  33. The crystal structure of tris(μ2-bromido)-bis(η6-p-cymene)-diosmium(II) tetrafluoroborate, C20H28BBr3F4Os2
  34. Crystal structure of new barium lithium manganese fluorides: Ba14Li1.87Mn14.13F68 with a Jarlite–related structure
  35. Crystal structure of (4-fluorobenzyl)triphenylphosphonium chloride, C25H21ClFP
  36. The crystal structure of calcitriol–chloroform (1/1), C27H44O3⋅CHCl3
  37. The crystal structure of (E)-1-((3)-nitrophenyl)pyren-3-(pyren-1-yl)prop-2-en-1-one, C25H15NO3
  38. Crystal structure of (E)-2-hydroxy-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H16N2O3
  39. Crystal structure of (E)-(3-(thiophen-2-yl)acryloyl)ferrocene, C17H14FeOS
  40. Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2
  41. Synthesis and crystal structure poly[diaqua(μ3-3-(((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl) methyl)ammonio)propanoate-κ3 O:O′:O″) sodium(I)] monohydrate, C20H24NNaO12S
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  43. Synthesis and crystal structure of 4-(difluoromethyl)-1-methyl-N-(pyridin-3-yl)-1H-pyrazole-3-carboxamide hydrate, C11H12F2N4O2
  44. The crystal structure of caesalfurfuric acid B, C22H32O4
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  48. The crystal structure of 1,1′-(2,5-dimethylpyrazine-1,4-diyl)bis(ethan-1-one), C10H14N2O2
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  50. The crystal structure of the double salt dipyridin-1-ium bromide tribromide
  51. Crystal structure of (E)-(3-(3-methylthiophen-2-yl)acryloyl)ferrocene, C18H16FeOS
  52. Crystal structure of (E)-(3-(4-phenoxyphenyl)acryloyl)ferrocene, C25H20FeO2
  53. Crystal structure of (E)-(3-(3,4-dimethylphenyl)acryloyl)ferrocene, C21H20FeO
  54. Crystal structure of [(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N‴)tetracyanidodiplatinum(II)] dimethyl sulfoxide solvate, C18H36N8O2Pt2S2
  55. Crystal structure of (4-ethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO2P
  56. Crystal structure of (1-naphthalen-1-yl-methyl)triphenylphosphonium chloride ethanol solvate, C31H30ClOP
  57. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N,N,N‴)platinum(II) bis[tribromido(dimethyl sulfoxide-κS)platinate(II)], C14H36Br6N4O2Pt3S2
  58. Crystal structure of (2-methylbenzyl)triphenylphosphonium chloride ethanol solvate, C28H30ClOP
  59. Crystal structure of bis(η2, σ1-8-methoxycyclooct-4-enyl)(μ2-1,4,8,11-tetraazacyclotetradecane-κ4 N, N, N, N‴)diplatinum(II) dibromide, C28H54Br2N4O2Pt2
  60. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N,N,N)palladium(II) tetrabromidopalladate(II), C10H24Br4N4Pd2
  61. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N,N,N‴)palladium(II) bis[trichlorido(dimethyl sulfoxide-κS)platinate(II)], C14H36Cl6N4O2PdPt2S2
  62. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetraiodidopalladate(II), C10H24I4N4Pd2
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