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Crystal structure of (5S,6E,8E,10E,13R,15S,16Z)-15,5,13,15-tetrahydroxy-16-methyl-2-aza-1(1,3)-benzenacyclononadecaphane-6,8,10,16-tetraen-3-one, C24H31NO5

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Veröffentlicht/Copyright: 29. Oktober 2025
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 241 Heft 1

Abstract

C24H31NO5, orthorhombic, P212121 (no. 19), a = 4.9020(10) Å, b = 17.638(4) Å, c = 24.848(5) Å, V = 2148.4(7) Å3, Z = 4, R gt (F) = 0.0751, wRref (F 2) = 0.1901, T = 293(2) K.

CCDC no.: 2466724

The molecular structure is shown in the figure. Table 1 contains the crystallographic data.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.20 × 0.10 × 0.05 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Nonius CAD-4, φ and ω scans
θ max, completeness: 25.3°, 100 %
N(hkl)measured, N(hkl)unique, R int: 4485, 3881, 0.078
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2112
N(param)refined: 264
Programs: Nonius, Olex2, 1 , 2 SHELX 3 , 4

1 Source of material

The title compound is a natural product, obtained by extraction and isolation from actinomycetes fermentation products. 5

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 3 , 4 refinement package. 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) (Table 1).

3 Comment

Ansamycins are a family of broad-spectrum bioactive macrolactams, such as antituberculosis rifamycin, 5 antitumor maytansine 6 , 7 and Hsp90 inhibitor geldanamycin. 8 The title compound of C24H31NO5, named demethyltrienomycinol, has been reported in 2008, but no three-dimensional coordinates were deposited with the Cambridge Crystallographic Data Centre in the reported literature. 5 , 6 , 7 The structure of C24H31NO5 is composed of a 21-membered macrocyclic lactam ring including a triene moiety, which formed through an amide linkage to the 3-amino-5-hydroxybenzoic acid (AHBA) fragment. The title compound crystallizes in the orthorhombic space group P212121. The geometry of title structure was characterized with the bond angles and lengths in accordance with the literature. 8 In particular, the torsion angles of C2⋯C3⋯C4⋯C5, C21⋯N⋯C1⋯C2, O2⋯C3⋯C4⋯C5, C9⋯C10⋯C11⋯O3, O4⋯C13⋯C14⋯C15 and C16⋯C17⋯C18⋯C19, are −113.9(6)°, 169.9(4)°, 126 (3)°, −69.5(6)°, −56.2(7)° and −70.9(6)°, respectively. Furthermore, the bond lengths of O1⋯C1, O2⋯C35, C4⋯C5, O5⋯C23, C10⋯C11,C14⋯C16 and N⋯C1, are 1.248(6) Å, 1.428(6) Å, 1.330(7) Å, 1.359(6) Å, 1.501(8) Å, 1.313(7) Å, and 1.332(6) Å, coincident with the reported parameters. 9 And it was further unequivocally secured that the stereo configurations of C3, C11 and C13 are S, R and S, respectively. 10 , 11 In the crystal, the molecules are arranged in layers via hydrogen bonds O5–H⋯O2 with max D–A distance 2.9 Å and minimum angle 120°. All bond angles and lengths of the title structure are within the expected range.

Corresponding author: Pu Cui, College of Life and Environment Sciences, Huangshan University, Huangshan, 245041, People’s Republic of China, E-mail:

Acknowledgements

This work was supported by the education natural science key project of Anhui Provice (2024AH051755), and the open research project of the rural revitalization collaborative technical service center of Anhui province (Huangshan University) (XCZXZD2402).

  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 education natural science key project of Anhui Provice (2024AH051755), and the open research project of the rural revitalization collaborative technical service center of Anhui province (Huangshan University) (XCZXZD2402).

References

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6. Maggi, N.; Pasqualucci, C.; Ballotta, R.; Sensi, P. Rifampicin: A New Orally Active Rifamycin. Chemotherapy 1966, 11, 285–292; https://doi.org/10.1159/000220462.Suche in Google Scholar PubMed

7. Cassady, J. M.; Chan, K. K.; Floss, H. G.; Leistner, E. Recent Developments in the Maytansinoid Antitumor Agents. Chem. Pharm. Bull. 2004, 52, 1–26; https://doi.org/10.1248/cpb.52.1.Suche in Google Scholar PubMed

8. Kusari, P.; Kusari, S.; Eckelmann, D.; Zuhlke, S.; Kayser, O.; Spiteller, M. Cross-Species Biosynthesis of Maytansine in Maytenus Serrata. RSC Adv. 2016, 6, 10011–10016; https://doi.org/10.1039/c5ra25042k.Suche in Google Scholar

9. Yamada, Y.; Tashiro, E.; Taketani, S.; Imoto, M.; Kataoka, T. Mycotrienin Ii, A Translation Inhibitor that Prevents Icam-1 Expression Induced by Pro-Inflammatory Cytokines. J. Antibiot. 2011, 64, 361–366; https://doi.org/10.1038/ja.2011.23.Suche in Google Scholar PubMed

10. Whitesell, L.; Mimnaugh, E. G.; Costa, B. D.; Neckers, M. L. M.; Neckers, L. M. Inhibition of Heat Shock Protein HSP90-pp60v-src Heteroprotein Complex Formation by Benzoquinone Ansamycins: Essential Role for Stress Proteins in Oncogenic Transformation. Proc. Natl. Acad. Sci. U. S. A. 1994, 91, 8324–8328; https://doi.org/10.1073/pnas.91.18.8324.Suche in Google Scholar PubMed PubMed Central

11. Sun, W.; Li, Y. P.; Jin, J.; Li, Z. R.; Shan, G. Z. Crystal Structure of 17-(2′-(1′-oxa-4′-aza-heterocyclohexyl-1′-)Ethylamino)-17-Demethoxygeldanamycin Dihydrate, C34H54N4O11. Z. Kristallogr.-N. Cryst. Struct. 2015, 230, 180–182; https://doi.org/10.1515/ncrs-2014-9073.Suche in Google Scholar
Received: 2025-06-27
Accepted: 2025-10-05
Published Online: 2025-10-29
Published in Print: 2026-02-25

© 2025 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 ( E )-4-chloro-7-(diethylamino)-3-(3-oxo-3-phenylprop-1-en-1-yl)-2 H -chromen-2-one C22H20ClNO3
  4. Crystal structure of (5S,6E,8E,10E,13R,15S,16Z)-15,5,13,15-tetrahydroxy-16-methyl-2-aza-1(1,3)-benzenacyclononadecaphane-6,8,10,16-tetraen-3-one, C24H31NO5
  5. The crystal structure of [bis(6-phenylpyridine-2-carboxylato-κ2O,N)-dihydrate-nickel(II)] ethanol solvate
  6. The crystal structure of poly[(μ3-2-nitro-1,3-phenyldicarboxylato-κ5 O, O′:O″,O″,O″′)-bis(N,N-dimethylpropionamide)calcium(II)], C18H25CaN3O8
  7. Solvothermal synthesis and crystal structure of poly((μ3-2-amino-1,3-benzenedicarboxylato-κ4O:O′,O″,O‴)-bis(μ4-2-amino-1,3-benzenedicarboxylato-κ5O:O:O′,O″,O‴)-(N,N-dimethylformamide)-aqua-di-europium(III)-N,N-dimethylformamide solvate, C30H31N5O7Eu2
  8. Crystal structure of (1R,4S,6S,6aS,9R,11bS,12S)-1,6,12-trihydroxy-4,11b-dimethyl-8-methylene-7-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalen-4-yl)methyl acetate
  9. Crystal structure of diaqua[bis(5-methyl-2-pyrazinecarboxylato-κ2N,O)]zinc(II), C12H14N4O6Zn
  10. Hydrogen bonding in the crystal structure of the organic salt (R)-1-phenylethan-1-aminium (R)-5-(1,2-dithiolan-3-yl)pentanoate – a salt of the lipoic acid
  11. The crystal structure of 5-amino-4-(4-amino-1-oxoisoindolin-2-yl)-5-oxopentanoic acid, C13H15N3O4
  12. Crystal structure of 2-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)benzaldehyde, C13H13O3N3S
  13. The crystal structure of 2,8,14,20-tetrapropylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18, 21,23-dodecaene-4,5,6,10,11,12,16,17,18,22,23,24-dodecol – acetone – water (1(3/3))
  14. Crystal structure of bis(m2-(2-oxidophenyl)-5-(pyridin-2-yl)pyrazolyl k4N,N′:N′′,O:O)-(μ2-acetic acid k2O:O)-(N,N-dimethylformamide k1O)dimanganese(II) N,N-dimethylformamide solvate, C36H36Mn2N8O6
  15. The crystal structure of 2,2′-difluoro-3,3′-dimethoxy-1,1′-biphenyl, C14H12F2O2
  16. The crystal structure of (E)-4-(2-methoxyphenoxy)-3-(2-(-1,3,3,6a-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)dihydrofuran-2(3H)-one, C30H40O6
  17. Crystal structure of 3-hydroxy-2-mesityl-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one – a Z′ = 3 structure –
  18. Crystal structure of bis(1,1′-biphenyl-2,2′-diolato-κ2O,O′)-bis (1H-pyrazole-κ1N)titanium(IV) pyrazole solvate, C36H32N8O4Ti
  19. Crystal structure of di-μ-azido -k1N bis[2-(1,10-phenanthrolin-2-yl)benzo[d]imidazol-1-ido-k3N,N′,N′′]-bis(methanol-k1O)-di-manganese
  20. Crystal structure of bis(acetato-κ1O)-bis methanol-κ1O)bis(1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol-κ1N)nickel(II)
  21. Crystal structure of (E)-(3-(4-fluorophenyl)acryloyl)ferrocene, C19H15FFeO
  22. The crystal structure of 5,7-dinitro-1,3,5,7-dioxadiazocane
  23. Crystal structure of 5-(2,5-dimethoxyphenyl)-8-methoxy-2-oxo-2H-chromene-6-carbaldehyde, C19H16O6
  24. The crystal structure of 2,5-diphenyloxazole–2,5-dihydroxyterephthalic acid (2/1), C19H14NO4
  25. Crystal structure of [bis(acetonitrile κ1N)-bis(μ2-3,3′-methylenebis(1-methyl-1,3-dihydro-2H-imidazole-2-thione)-κ2S,S)iron(II) diperchlorate], C22H30Cl2FeN10O8S4
  26. The crystal structure of N-((4-chloro-5-(3-nitrophenyl)-2H-1,2,3-triazol-2-yl)methyl)acetamide, C11H10ClN5O3
  27. The crystal structure of 2-benzylsuccinic acid, C11H12O6 Z. Kristallogr. - New Cryst. Struct.
  28. The crystal structure of tert-butyl 3-(1-benzoyl-5-methyl-3-oxo-4-phenethyl-1,2,3,4-tetrahydropyrazin-2-yl)-1H-indole-1-carboxylate, C33H33N3O4
  29. The crystal structure of 4-dimethylaminoantipyrine hydrochloride, C13H18N3OCl
  30. Crystal structure of poly[μ2-3-(pyrazin-2-yl)-1,2,4-triazolato-k3N:N′,N′′)(μ2-formato-k2O:O′)copper(II)], C7H5CuN5O2
  31. Synthesis and crystal structure of 4-(ethoxycarbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO4
  32. Crystal structure of (4-(3,4-dimethylphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C23H21FeNO
  33. Crystal structure of (4-(2,4-dimethoxyphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C23H21FeNO3
  34. The crystal structure of bis(1-(2-chloroethyl)pyrrolidin-1-ium) hexachloridotin(IV), C12H22Cl8N2Sn
  35. Co-crystallization of isonicotinamide with diphenic acid: formation of a supramolecular adduct
  36. Erratum
  37. Erratum
https://doi.org/10.1515/ncrs-2025-0289
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Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of ( E )-4-chloro-7-(diethylamino)-3-(3-oxo-3-phenylprop-1-en-1-yl)-2 H -chromen-2-one C22H20ClNO3
  4. Crystal structure of (5S,6E,8E,10E,13R,15S,16Z)-15,5,13,15-tetrahydroxy-16-methyl-2-aza-1(1,3)-benzenacyclononadecaphane-6,8,10,16-tetraen-3-one, C24H31NO5
  5. The crystal structure of [bis(6-phenylpyridine-2-carboxylato-κ2O,N)-dihydrate-nickel(II)] ethanol solvate
  6. The crystal structure of poly[(μ3-2-nitro-1,3-phenyldicarboxylato-κ5 O, O′:O″,O″,O″′)-bis(N,N-dimethylpropionamide)calcium(II)], C18H25CaN3O8
  7. Solvothermal synthesis and crystal structure of poly((μ3-2-amino-1,3-benzenedicarboxylato-κ4O:O′,O″,O‴)-bis(μ4-2-amino-1,3-benzenedicarboxylato-κ5O:O:O′,O″,O‴)-(N,N-dimethylformamide)-aqua-di-europium(III)-N,N-dimethylformamide solvate, C30H31N5O7Eu2
  8. Crystal structure of (1R,4S,6S,6aS,9R,11bS,12S)-1,6,12-trihydroxy-4,11b-dimethyl-8-methylene-7-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalen-4-yl)methyl acetate
  9. Crystal structure of diaqua[bis(5-methyl-2-pyrazinecarboxylato-κ2N,O)]zinc(II), C12H14N4O6Zn
  10. Hydrogen bonding in the crystal structure of the organic salt (R)-1-phenylethan-1-aminium (R)-5-(1,2-dithiolan-3-yl)pentanoate – a salt of the lipoic acid
  11. The crystal structure of 5-amino-4-(4-amino-1-oxoisoindolin-2-yl)-5-oxopentanoic acid, C13H15N3O4
  12. Crystal structure of 2-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)benzaldehyde, C13H13O3N3S
  13. The crystal structure of 2,8,14,20-tetrapropylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18, 21,23-dodecaene-4,5,6,10,11,12,16,17,18,22,23,24-dodecol – acetone – water (1(3/3))
  14. Crystal structure of bis(m2-(2-oxidophenyl)-5-(pyridin-2-yl)pyrazolyl k4N,N′:N′′,O:O)-(μ2-acetic acid k2O:O)-(N,N-dimethylformamide k1O)dimanganese(II) N,N-dimethylformamide solvate, C36H36Mn2N8O6
  15. The crystal structure of 2,2′-difluoro-3,3′-dimethoxy-1,1′-biphenyl, C14H12F2O2
  16. The crystal structure of (E)-4-(2-methoxyphenoxy)-3-(2-(-1,3,3,6a-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)dihydrofuran-2(3H)-one, C30H40O6
  17. Crystal structure of 3-hydroxy-2-mesityl-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one – a Z′ = 3 structure –
  18. Crystal structure of bis(1,1′-biphenyl-2,2′-diolato-κ2O,O′)-bis (1H-pyrazole-κ1N)titanium(IV) pyrazole solvate, C36H32N8O4Ti
  19. Crystal structure of di-μ-azido -k1N bis[2-(1,10-phenanthrolin-2-yl)benzo[d]imidazol-1-ido-k3N,N′,N′′]-bis(methanol-k1O)-di-manganese
  20. Crystal structure of bis(acetato-κ1O)-bis methanol-κ1O)bis(1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol-κ1N)nickel(II)
  21. Crystal structure of (E)-(3-(4-fluorophenyl)acryloyl)ferrocene, C19H15FFeO
  22. The crystal structure of 5,7-dinitro-1,3,5,7-dioxadiazocane
  23. Crystal structure of 5-(2,5-dimethoxyphenyl)-8-methoxy-2-oxo-2H-chromene-6-carbaldehyde, C19H16O6
  24. The crystal structure of 2,5-diphenyloxazole–2,5-dihydroxyterephthalic acid (2/1), C19H14NO4
  25. Crystal structure of [bis(acetonitrile κ1N)-bis(μ2-3,3′-methylenebis(1-methyl-1,3-dihydro-2H-imidazole-2-thione)-κ2S,S)iron(II) diperchlorate], C22H30Cl2FeN10O8S4
  26. The crystal structure of N-((4-chloro-5-(3-nitrophenyl)-2H-1,2,3-triazol-2-yl)methyl)acetamide, C11H10ClN5O3
  27. The crystal structure of 2-benzylsuccinic acid, C11H12O6 Z. Kristallogr. - New Cryst. Struct.
  28. The crystal structure of tert-butyl 3-(1-benzoyl-5-methyl-3-oxo-4-phenethyl-1,2,3,4-tetrahydropyrazin-2-yl)-1H-indole-1-carboxylate, C33H33N3O4
  29. The crystal structure of 4-dimethylaminoantipyrine hydrochloride, C13H18N3OCl
  30. Crystal structure of poly[μ2-3-(pyrazin-2-yl)-1,2,4-triazolato-k3N:N′,N′′)(μ2-formato-k2O:O′)copper(II)], C7H5CuN5O2
  31. Synthesis and crystal structure of 4-(ethoxycarbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO4
  32. Crystal structure of (4-(3,4-dimethylphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C23H21FeNO
  33. Crystal structure of (4-(2,4-dimethoxyphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C23H21FeNO3
  34. The crystal structure of bis(1-(2-chloroethyl)pyrrolidin-1-ium) hexachloridotin(IV), C12H22Cl8N2Sn
  35. Co-crystallization of isonicotinamide with diphenic acid: formation of a supramolecular adduct
  36. Erratum
  37. Erratum
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