Startseite Crystal structure of (R)(R)-5-chloro-3-((S,1E,3E)-3,5-dimethyl-hepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-2,6,7,8-tetrahydroisoquinolin-7-yl acetate, C21H24ClNO4
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Crystal structure of (R)(R)-5-chloro-3-((S,1E,3E)-3,5-dimethyl-hepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-2,6,7,8-tetrahydroisoquinolin-7-yl acetate, C21H24ClNO4

  • Shu-Feng Bi , Hong-Lei Li ORCID logo , Fei-Fei Li und Xiang-Yang Chen
Veröffentlicht/Copyright: 6. September 2024

Abstract

C21H24CINO4, monoclinic, P21 (no. 14), a = 8.6813(3) Å, b = 7.3821(2) Å, c = 16.0325(6) Å, β = 105.282(2)°, V = 991.13(6) Å3, Z = 2, R gt(F) = 0.0405, wR ref(F 2) = 0.1014, T = 296.15 K.

CCDC no.: 2348404

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: Red needle
Size: 0.28 × 0.15 × 0.10 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 0.22 mm−1
Diffractometer, scan mode: Bruker P4, ω
θ max, completeness: 27.9°, >99 %
N(hkl)measured, N(hkl)unique, R int: 15860, 4621, 0.033
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3735
N(param)refined: 252
Programs: Olex2, 1 , 2 SHELX 3 , 4
Table 2:

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

Atom x y z U iso*/U eq
C1 0.8155 (3) 0.3956 (5) 0.36708 (17) 0.0336 (6)
C3 0.8946 (3) 0.4085 (5) 0.51986 (16) 0.0332 (6)
C4 0.7381 (3) 0.4134 (5) 0.52163 (17) 0.0340 (6)
C5 0.4504 (3) 0.4150 (5) 0.44303 (16) 0.0328 (6)
C6 0.3242 (3) 0.4171 (5) 0.36775 (16) 0.0313 (6)
C7 0.3690 (3) 0.4414 (4) 0.28128 (17) 0.0317 (6)
C8 0.5378 (3) 0.3845 (4) 0.28142 (17) 0.0337 (6)
C9 1.0284 (3) 0.4089 (5) 0.59771 (17) 0.0367 (6)
C10 1.0275 (3) 0.3142 (4) 0.66721 (19) 0.0375 (7)
C11 1.1521 (3) 0.3023 (4) 0.7484 (2) 0.0367 (7)
C12 1.1324 (4) 0.1892 (5) 0.8089 (2) 0.0451 (8)
C13 1.2414 (4) 0.1551 (6) 0.8979 (2) 0.0516 (9)
C14 1.2179 (5) −0.0362 (7) 0.9276 (3) 0.0710 (12)
C15 1.3464 (7) −0.0961 (11) 1.0063 (4) 0.115 (2)
C16 1.2133 (6) 0.2974 (7) 0.9604 (3) 0.0772 (13)
C17 1.2947 (4) 0.4251 (6) 0.7595 (2) 0.0539 (9)
C18 0.3543 (4) 0.6407 (4) 0.2567 (2) 0.0435 (8)
C19 0.2457 (4) 0.1689 (5) 0.2252 (2) 0.0404 (7)
C20 0.1074 (5) 0.0876 (6) 0.1604 (3) 0.0656 (11)
C21 0.6103 (3) 0.4091 (5) 0.44447 (15) 0.0301 (5)
C22 0.6582 (3) 0.3972 (5) 0.36516 (16) 0.0316 (6)
Cl1 0.39620 (8) 0.41451 (13) 0.54013 (4) 0.0456 (2)
H1 1.023 (4) 0.408 (6) 0.4420 (19) 0.043*
H7 0.714105 0.419778 0.574764 0.041*
H9 0.844461 0.388791 0.315300 0.040*
H10 1.117772 0.478740 0.598111 0.044*
H11 0.935853 0.246350 0.664171 0.045*
H13 1.038800 0.121459 0.794599 0.054*
H14 1.351979 0.166268 0.894354 0.062*
H15A 1.115170 −0.042867 0.940769 0.085*
H15B 1.215475 −0.119588 0.880576 0.085*
H16A 1.306118 −0.192321 1.034882 0.173*
H16B 1.377033 0.004212 1.045210 0.173*
H16C 1.437546 −0.138294 0.988604 0.173*
H17A 1.371654 0.397295 0.812935 0.081*
H17B 1.261343 0.548981 0.760272 0.081*
H17C 1.341920 0.407420 0.712265 0.081*
H18A 1.233217 0.415402 0.940354 0.116*
H18B 1.284197 0.276321 1.016557 0.116*
H18C 1.104755 0.290498 0.963866 0.116*
H20A 0.125220 −0.039885 0.155616 0.098*
H20B 0.096197 0.144363 0.105278 0.098*
H20C 0.011777 0.105937 0.178691 0.098*
H21A 0.373926 0.656168 0.200940 0.065*
H21B 0.431065 0.709387 0.298927 0.065*
H21C 0.248674 0.682383 0.254724 0.065*
N1 0.9305 (3) 0.4036 (4) 0.44192 (14) 0.0360 (5)
O1 0.18009 (19) 0.4126 (4) 0.36458 (12) 0.0441 (5)
O2 0.5699 (2) 0.3456 (4) 0.21459 (14) 0.0495 (7)
O3 0.2532 (2) 0.3499 (3) 0.21400 (13) 0.0357 (5)
O4 0.3378 (3) 0.0903 (3) 0.28234 (17) 0.0552 (6)

1 Source of material

The title compound is a natural product, which has been totally synthesized in 2011. 5 We got it by extraction and isolation from fungal fermentation products. 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 U iso (H) fixed at 1.2 times of U eq (C) (Tables 1 and 2).

3 Comment

The title compound of C21H24CINO4 has been reported with various biological activities, such as neuroprotective effects, and cytotoxic against hepatoma cells. 7 , 8 The structure of C21H24CINO4 is composed of 4,6-dimethylocta-2,4-diene, pyridine ring, and m-benzoquinone ring moiety. 9 The geometry of title structure was characterized with the bond angles and lengths. In particular, the bond angles for C6⋯C7⋯C8, C5⋯C6⋯C7, C6⋯C5⋯CI1 and C1⋯N1⋯C3 are 115.8(2)°, 116.7 (2)°, 115.85(17)° and 121.5(2)°, respectively. For another, the bond lengths of CI1⋯C5, O1⋯C6, O2⋯C8, C5⋯C6 and C1⋯N1, are 1.741(2) Å, 1.239(3) Å, 1.435(3) Å, 1.400(4) Å, 1.345(3) Å. Furthermore, the molecules are connected by intermolecular hydrogen bonds N1-H1⋯O1, C9-H10⋯CI1, C10-H11⋯O1, which are 2.07 Å/145°, 2.85 Å/133°, 2.66 Å/142°, respectively. These bond lengths are within the normal range. 9 , 10 , 11 In the structure, the pyridine ring and benzoquinone formed a rare isoquinoline quinone skeleton, and it was further unequivocally secured that the stereo configurations of C-7 and C-13 are 7R and 13S (coincident with the reported). 9


Corresponding authors: Xiang-Yang Chen, College of Life and Environment Sciences, Huangshan University, Huangshan 245041, People’s Republic of China; and Fei-Fei Li, Department of Pharmacy, Kangda College of Nanjing Medical University, Lianyungang 222000, People’s Republic of China, E-mail: (X.-Y. Chen), (F.-F. Li)

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

  2. Research funding: This work was supported by the Huangshan University school-enterprise cooperation project (hxkt2024095, hxkt2020118), Natural Science Foundation for Colleges and Universities of Jiangsu Province (No. 20KLB350007).

  3. Competing interests: The authors declare no conflicts of interest regarding this article.

References

1. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. Olex2: A Complete Structure Solution, Refinement and Analysis Program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Suche in Google Scholar

2. Bourhis, L. J.; Dolomanov, O. V.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. The Anatomy of a Comprehensive Constrained, Restrained Refinement Program for the Modern Computing Environment–Olex2 Dissected. Acta Crystallogr. 2015, 71, 59–75; https://doi.org/10.1107/s2053273314022207.Suche in Google Scholar

3. Sheldrick, G. M. A Short History of Shelx. Acta Crystallogr. 2008, 64, 112–122; https://doi.org/10.1107/s0108767307043930.Suche in Google Scholar PubMed

4. Sheldrick, G. M. Crystal Structure Refinement with Shelxl. Acta Crystallogr. 2015, 71, 3–8; https://doi.org/10.1107/s2053229614024218.Suche in Google Scholar

5. Germain, A. R.; Bruggemeyer, D. M.; Zhu, J. l.; Genet, C.; Brien, P. O.; Porco Jr, J. A. Synthesis of the Azaphilones (+)-Sclerotiorin and (+)-8-O-Methylsclerotiorinamine Utilizing (+)-Sparteine Surrogates in Copper-Mediated Oxidative Dearomatization. J. Org. Chem. 2011, 76, 2577–2584; https://doi.org/10.1021/jo102448n.Suche in Google Scholar PubMed PubMed Central

6. Li, J.; Yang, X.; Lin, Y. Y.; Yun, J.; Lu, Y. J.; Zhu, X.; Li, J.; Li, M. F.; Lin, Y. C.; He, J. G.; Liu, L. Meroterpenes and Azaphilones from Marine Mangrove Endophytic Fungus Penicillium 303#. Fitoterapia 2014, 97, 241–246; https://doi.org/10.1016/j.fitote.2014.06.011.Suche in Google Scholar PubMed

7. Li, J. L.; Li, Z. X.; Chen, T.; Ye, G. T.; Qiu, L. Y.; Long, Y. H. New Azaphilones from Mangrove Endophytic Fungus Penicillium Sclerotiorin SCNU-F0040. Nat. Prod. Res. 2023, 37, 296–304; https://doi.org/10.1080/14786419.2021.1959580.Suche in Google Scholar PubMed

8. Guo, Q. F.; Dong, L. L.; Zang, X. Y.; Gu, Z. J.; He, X. Y.; Yao, L. D.; Cao, L.; Qiu, J. Z.; Guan, X. A New Azaphilone from the Entomopathogenic Fungus Hypocrella sp. Nat. Prod. Res. 2015, 29, 1–7; https://doi.org/10.1080/14786419.2015.1023199.Suche in Google Scholar PubMed

9. Yang, W. C.; Yuan, J.; Tan, Q.; Gu, Z. J.; He, X. Y.; Yao, L. D.; Cao, L. P.; Qiu, J. Z.; Guan, X. Peniazaphilones A–I, Produced by Co-Culturing of Mangrove Endophytic Fungi, Penicillium sclerotiorum THSH-4 and Penicillium sclerotiorum ZJHJJ-18. Chin. J. Chem. 2021, 39, 3404–3412; https://doi.org/10.1002/cjoc.202100542.Suche in Google Scholar

10. Whalley, W. B.; Ferguson, G.; Marsh, W. C.; Restivo, R. J. The Chemistry of Fungi. Part LXVIII. The Absolute Configuration of (+)-sclerotiorin and of the Azaphilones. J. Chem. Soc., Perkin Trans. 1976, 1, 1366–1369; https://doi.org/10.1039/p19760001366.Suche in Google Scholar

11. Hebra, T.; Elie, N.; Poyer, S.; Van Elslande, E.; Touboul, D.; Eparvier, V. Dereplication, Annotation, and Characterization of 74 Potential Antimicrobial Metabolites from Penicillium Sclerotiorum Using t-SNE Molecular Networks. Metabolites 2021, 11, 444; https://doi.org/10.3390/metabo11070444.Suche in Google Scholar PubMed PubMed Central

Received: 2024-07-11
Accepted: 2024-08-23
Published Online: 2024-09-06
Published in Print: 2024-12-17

© 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. Crystal structure of 3-nitrophenol-2,1,3-benzoselenadiazole (1/1), C12H9N3O3Se
  4. Crystal structure of diaqua-(hydroxido)-{μ-[2-(hydroxy)-5-[(4-nitrophenyl)diazenyl]benzoato]}-{2-hydroxy-5-[(4-nitrophenyl)diazenyl]benzoato}-(1,10-phenanthroline)-diterbium hydrate, C38H27.4N8O12.2Tb
  5. Crystal structure of poly[bis(μ3-3-fluoro-4-(1H-1,2,4-triazol-1-yl)benzoato-κ3 O:O′:N)cadmium(II)] – dimethylformamide (1/1), C21H17CdF2N7O5
  6. The crystal structure of 2-amino-N-(pyridin-2-yl)benzamide, C12H11N3O
  7. The crystal structure of 2,3-di(pyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one, C18H14N4O
  8. Crystal structure of 2-chloro-4-fluorobenzyl (R)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18ClFO3
  9. Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid]-(methylsulfinyl)methane, C15H16N2O6S
  10. The crystal structure of 2-ethyl-1,1-dimethyl-1H-benzo[e]indole, C16H17N
  11. The crystal structure of (Z)-5-amino-N -hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  12. The crystal structure of 2,2,5-trimethyl-3-(4-(4-(5-phenyl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)phenyl)imidazolidin-4-one, C24H24N4O2S
  13. The crystal structure of tetrakis(μ2-acetato-κ2 O:O′)-bis[(4′-phenyl-4,2′:6′,4″-terpyridine-κ1 N)dicopper(II)], C25H21CuN3O4
  14. Crystal structure of poly(3-thiophenecarboxylato-κ 3 O,O′:O′)-(methanol-κO)cadmium(II), C11H10O5S2Cd
  15. The crystal structure of dichloridobis[4′-(p-methoxylphenyl)-4,2′:6′,4″-terpyridine-κN] zinc(II), C44H34Cl2N6O2Zn
  16. The crystal structure of 1-(2-carboxyethyl)-1H-imidazole 3-oxide
  17. Crystal structure of 1,1′,1″-(nitrilotris(ethane-2,1-diyl))tris(3-(4-(((E)-pyridin-2-ylmethylene)amino)phenyl)urea), C45H47N13O4
  18. Crystal structure of a (E)-4-bromo-N-(4-(diethylamino)-2-hydroxybenzylidene) benzenaminium acetate ─ 4-bromoaniline (1/1)
  19. Crystal structure of 2,2′-(iminobis(methylene))bis(benzimidazolium) bis(p-toluenesulfonate), C30H31N5O6S2
  20. The crystal structure of alogliptinium meta-chlorobenzoate
  21. Crystal structure of 4-bromobenzyl 2-(6-methoxy-naphthalen-2-yl)propanoate, C21H19BrO3
  22. The hydrated double salt structure of (E)-4-(2-benzylidenehydrazine-1-carbonyl)pyridin-1-ium cation with 2-hydroxybenzoate and benzoate anions
  23. Crystal structure of (R)(R)-5-chloro-3-((S,1E,3E)-3,5-dimethyl-hepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-2,6,7,8-tetrahydroisoquinolin-7-yl acetate, C21H24ClNO4
  24. The crystal structure of bis(3-oxo-1,3-diphenylprop-1-en-1-olato-κ 2 O:O′)-bis(1,4-dioxane-κ 1 O)nickel(II), C38H38O8Ni
  25. Crystal structure of poly[aqua-(pyridine-3-carboxylato-κ1 N)(pyridine-3-carboxylato-κ2 O,O′) cadmium(II)] dihydrate, C12H14N2O7Cd
  26. The crystal structure of 4-(4-phenyl-5-(((1-(2,4,6-tribromophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-4H-1,2,4-triazol-3-yl)pyridine, C22H14Br3N7S
  27. The crystal structure of N-benzylquinoline-2-carbothioamide, C17H14N2S
  28. Crystal structure of bis(3-isopropylphenyl)-4,4′-bipyridinium dichloride dihydrate, C28H30N2⋅2Cl⋅2H2O
  29. The crystal structure of ethyl 2-amino-4-(cyanophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C19H18N2O4
  30. Crystal structure of (4R,10S)-6-hydroxy-7-isopropyl-4,10-dimethyl-1,2,3,5-hexahydro-6,10-epoxyazulen-9-one, C15H22O3
  31. The crystal structure of (E)-(2-(2-hydroxy-3-methoxybenzylidene)aminophenyl)arsonic acid, C14H14AsNO5
  32. The crystal structure of poly[(μ 2-2-aminoisophthalato-κ4O,O′:O″:O″′)-(N-methylpyrrolidone κ1O)-dioxido-uranium(VI)], C13H14N2O7U
  33. The crystal structure of the co-crystal isonicotinamide · terephthalic acid, C8H6O4·2(C6H6N2O)
  34. The crystal structure of (E)-1-phenyl-3-(p-tolylthio)but-2-en-1-one, C17H16OS
  35. The crystal structure of 4,5-bis((Z)-chloro(hydroxyimino)methyl)-1H-imidazol-3-ium chloride monohydrate
  36. The crystal structure of 1,2-bis(4-(dimethylamino)phenyl)ethane-1,2-dione. C18H20N2O2
  37. Crystal structure of 2-chloro-4-fluorobenzyl 2-acetoxybenzoate, C16H12ClFO4
  38. Crystal structure of methyl 1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate, C19H14N2O2
  39. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl)(5-fluoro-2-iodophenyl)methanone, C19H17FINO4
  40. Crystal structure of tetrachlorido-bis(1-[(1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2 N:N′)dicopper, C36H32Cu2N24Cl4
  41. Crystal structure of 2-(2,3-bis(4-methoxyphenyl)-1H-pyrrolo[2,3-b]quinoxalin-1-yl)anilin, C30H24N4O2
  42. Crystal structure of 5,7-dihydroxy-2-phenyl-4H-chromen-4-one–N,N-dimethylformamide(1/1), C18H17NO5
  43. The crystal structure of bis(μ 2-biphenyl-2,2′-dicarboxylato)-diaqua-bis(nitrato)-bis(2,2′:6′,2′′-terpyridine)dineodymium(III), C46H32I2N8Nd2O16
  44. Crystal structure of (Z)-4-amino-N -((4-chlorophenyl)(phenyl)methylene)benzohydrazide, C20H16ClN3O
  45. Crystal structure of (E)-6,8-dimethoxy-4-(4-morpholinobenzylidene)-3,4-dihydro-1-benzoxepin-5(2H)-one, C23H25NO5
  46. Crystal structure of (R)-2-((3-(3-aminopiperidin-1-yl)-6-methyl-5-oxo-1,2,4-triazin-4(5H)-yl) methyl)-4-fluorobenzonitrile benzoate monohydrate, C24H27FN6O4
  47. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylato-κ 3 N,O,O)copper(II)]monohydrate, C12H15NO9Cu
  48. Crystal structure of (((4-chlorophenyl)sulfonyl)glycinato-κ 2 N,O)bis(1,10-phenanthroline-κ 2 N,N′)cobalt(II) tetrahydrate, C32H30ClCoN5O8S
  49. Crystal structure of (((3-nitrophenyl)sulfonyl)-β-alaninato-κO)bis(2,2′-bipyridine-κ 2 N, N′)copper(II) 3-nitrobenzenesulfonate, C35H29CuN7O11S2
  50. Crystal structure of 3-phenoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C27H24O4
  51. 6-(2′,3′-Dihydroxy-3′-methylbutyl)-7-methoxy-8-(3″-methylbut-2″-en-1″-yl)-2H-chromen-2-one, C20H26O5
  52. Crystal structure of bromido-(2,2′:6′,2″-terpyridine-4′-onato-κ3N)palladium(II) methanol solvate
  53. The crystal structure of ethyl 2-amino-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H22N2O6
  54. Crystal structure of (1E,3E,5E)-1,6-bis(4-(pentyloxy)phenyl)hexa-1,3,5-triene, C28H36O2
  55. The crystal structure of tris(2-bromo-4-methylphenyl)amine, C21H18Br3N
  56. The crystal structure of 3-(2,5-dimethylanilino)-1-(2,5-dimethylphenyl)-4-methyl-1H-pyrrole-2,5-dione, C21H22N2O2
  57. Crystal structure of dicarbonyl (μ2-indole-2-carboxylato κ2 O:O′)tris(triphenylarsine-κAs)dirhodium(I) acetone solvate, C68H56As3NO5Rh2
  58. The crystal structure of 4-chloro-2-formylphenyl 4-methylbenzenesulfonate, C14H11ClO4S
  59. Crystal structure of 4-iodobenzyl 2-(6-methoxynaphthalen-2-yl) propanoate, C21H19IO3
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