Startseite Crystal structure of 14-O-acetyldelcosine, C26H41NO8
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Crystal structure of 14-O-acetyldelcosine, C26H41NO8

  • Huan-Ni Liu , Yi-Kun Hao , Neng-Hua Chen und Lai-Ming Li ORCID logo EMAIL logo
Veröffentlicht/Copyright: 21. November 2022

Abstract

C26H41NO8, orthorhombic, P212121 (no. 19), a = 8.24370(10) Å, b = 13.1867(2) Å, c = 22.8490(4) Å, V = 2483.85(6) Å3, Z = 4, Rgt (F) = 0.0357, wRref (F 2) = 0.0975, T = 169.99(10) K.

CCDC no.: 2217908

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: 0.15 × 0.13 × 0.10 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 0.80 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 73.7°, 99%
N(hkl)measured, N(hkl)unique, R int: 11,294, 4713, 0.026
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 4616
N(param)refined: 325
Programs: CrysAlisPRO [1], Olex2 [2, 3], SHELX [4]
Table 2:

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

Atom x y z U iso*/U eq
C1 0.7956 (2) 0.50370 (17) 0.39373 (10) 0.0256 (4)
H1A 0.847524 0.458957 0.365058 0.031*
C2 0.8512 (3) 0.4694 (2) 0.45373 (11) 0.0338 (5)
H2A 0.828855 0.397648 0.458469 0.041*
H2B 0.967391 0.479378 0.457309 0.041*
C3 0.7647 (3) 0.5288 (2) 0.50112 (10) 0.0344 (5)
H3A 0.801845 0.598540 0.500115 0.041*
H3B 0.793543 0.500744 0.538956 0.041*
C4 0.5766 (3) 0.52728 (18) 0.49463 (10) 0.0268 (5)
C5 0.5232 (2) 0.45535 (16) 0.44418 (9) 0.0217 (4)
H5 0.548326 0.384413 0.453196 0.026*
C6 0.3401 (2) 0.47056 (15) 0.43253 (9) 0.0208 (4)
H6 0.293106 0.505222 0.466480 0.025*
C7 0.3312 (2) 0.54438 (16) 0.37903 (9) 0.0194 (4)
C8 0.2940 (2) 0.48856 (15) 0.32082 (9) 0.0211 (4)
C9 0.4078 (2) 0.39600 (16) 0.31399 (9) 0.0215 (4)
H9 0.363592 0.337474 0.335077 0.026*
C10 0.5832 (2) 0.41749 (16) 0.33411 (9) 0.0224 (4)
H10 0.631842 0.352317 0.344934 0.027*
C11 0.6071 (2) 0.49028 (16) 0.38642 (9) 0.0206 (4)
C12 0.6715 (3) 0.45519 (18) 0.27704 (9) 0.0272 (5)
H12A 0.715712 0.522637 0.282732 0.033*
H12B 0.759170 0.409579 0.266608 0.033*
C13 0.5408 (3) 0.45607 (18) 0.22913 (9) 0.0266 (5)
H13 0.588187 0.441289 0.190727 0.032*
C14 0.4326 (3) 0.36978 (17) 0.24931 (10) 0.0257 (4)
H14 0.491369 0.305424 0.246022 0.031*
C15 0.2974 (3) 0.56062 (16) 0.26763 (9) 0.0242 (4)
H15A 0.203764 0.545568 0.243457 0.029*
H15B 0.284484 0.629387 0.281961 0.029*
C16 0.4488 (3) 0.55801 (18) 0.22823 (9) 0.0257 (4)
H16 0.523110 0.611627 0.240981 0.031*
C17 0.5075 (2) 0.58758 (16) 0.37614 (9) 0.0196 (4)
H17 0.529234 0.613961 0.336820 0.024*
C18 0.5034 (3) 0.49664 (19) 0.55309 (10) 0.0312 (5)
H18A 0.536570 0.544193 0.583183 0.037*
H18B 0.385926 0.497936 0.550526 0.037*
C19 0.5151 (3) 0.63504 (17) 0.48061 (9) 0.0271 (5)
H19A 0.398644 0.637759 0.486562 0.033*
H19B 0.565066 0.683011 0.507263 0.033*
C20 0.4967 (3) 0.76764 (16) 0.40648 (10) 0.0273 (5)
H20A 0.387847 0.776995 0.421675 0.033*
H20B 0.492477 0.776065 0.364331 0.033*
C21 0.6074 (3) 0.84748 (18) 0.43235 (12) 0.0350 (5)
H21A 0.574192 0.913334 0.419032 0.053*
H21B 0.717002 0.834855 0.420135 0.053*
H21C 0.601303 0.844901 0.474276 0.053*
C22 0.2288 (3) 0.3225 (2) 0.47661 (11) 0.0367 (6)
H22A 0.172823 0.260315 0.468307 0.055*
H22B 0.165421 0.362483 0.503286 0.055*
H22C 0.332150 0.307652 0.493932 0.055*
C23 0.1832 (3) 0.28837 (18) 0.22702 (10) 0.0302 (5)
C24 0.0282 (3) 0.2997 (2) 0.19410 (13) 0.0417 (6)
H24A −0.009197 0.368431 0.197165 0.063*
H24B −0.051791 0.254807 0.210245 0.063*
H24C 0.045827 0.283149 0.153682 0.063*
C25 0.5133 (4) 0.6211 (2) 0.13365 (11) 0.0407 (6)
H25A 0.465460 0.645563 0.098029 0.061*
H25B 0.589279 0.568153 0.124785 0.061*
H25C 0.568554 0.675751 0.152987 0.061*
C26 0.5076 (5) 0.3691 (3) 0.62518 (13) 0.0576 (9)
H26A 0.391674 0.373603 0.628317 0.086*
H26B 0.556884 0.413509 0.653298 0.086*
H26C 0.541259 0.300577 0.632617 0.086*
N1 0.5524 (2) 0.66417 (13) 0.42028 (8) 0.0223 (4)
O1 0.85168 (19) 0.60412 (13) 0.38212 (8) 0.0311 (4)
H1 0.794405 0.645016 0.399559 0.047*
O2 0.25227 (18) 0.37757 (12) 0.42371 (7) 0.0262 (3)
O3 0.21858 (17) 0.62386 (11) 0.38845 (7) 0.0232 (3)
H3 0.126230 0.602606 0.383232 0.035*
O4 0.12791 (17) 0.45398 (12) 0.32342 (7) 0.0255 (3)
H4 0.114672 0.419847 0.353031 0.038*
O5 0.2857 (2) 0.36506 (12) 0.21506 (7) 0.0282 (3)
O6 0.2158 (3) 0.22038 (14) 0.26007 (9) 0.0428 (4)
O7 0.3905 (2) 0.58278 (14) 0.17064 (7) 0.0351 (4)
O8 0.5563 (2) 0.39794 (15) 0.56787 (7) 0.0390 (4)

Source of material

The dry seeds of Delphinium grandiflorum were purchased from Kaiyuan, Liaoning Province, China. Dried powder (50.0 kg) was extracted three times with 95% ethanol at room temperature. The solution was evaporated under reduced pressure to get a residue (6.5 kg). The crude extract was suspended in water and we adjusted pH to 2–3 with HCl, and then partitioned with dichloromethane. The aqueous layer was adjusted to pH 9–10 with ammonium hydroxide and extracted by dichloromethane. After evaporation the dichloromethane soluble fraction (400 g) was obtained. This fraction was chromatographed by macroporous resins, eluted with EtOH/H2O solvent system, which afforded four fractions (fr. 1–4). The title compound was obtained from fr.4 and crystallized in methanol.

Experimental details

A suitable crystal was selected and mounted on a SuperNova, Dual, Cu at zero, AtlasS2 diffractometer. Using Olex2 [2], the structure was solved with the ShelXT [3] and refined with ShelXL [4]. Refinement package using least squares.

Comment

The plant D. grandiflorum belongs to Ranunculaceae Juss. It is originated in southern Europe and is now widely distributed throughout China [5]. Previous chemical investigations of D. grandiflorum have revealed that diterpene alkaloids are the main chemical constituents of this plant [6]. The single crystals were obtained by slow evaporation from a methanol solution.

The title compound was determined structurally as 14-O-acetyldelcosine [7], which is belonging to a class of diterpene alkaloids. The C=O bond length is 1.203 Å, the C–O bond lengths have values of 1.346(2)–1.444(8) Å, and the C–N and C–C bond lengths are within normal ranges [8, 9].


Corresponding author: Lai-Ming Li, College of Pharmacy, Southwest Minzu University, Chengdu, 610041, P. R. China, E-mail:
Huan-Ni Liu and Yi-Kun Hao contributed equally to this work.

Award Identifier / Grant number: ZYN2022059

Award Identifier / Grant number: X202210656418

Award Identifier / Grant number: 82173695

Award Identifier / Grant number: 82003609

Funding source: Guangdong Basic and Applied Basic Research Foundation

Award Identifier / Grant number: 2020B1515020033

Award Identifier / Grant number: 2020A1515110415

Award Identifier / Grant number: 2020A1515110453

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

  2. Research funding: “The Fundamental Research Funds for the Central Universities”, Southwest Minzu University (No. ZYN2022059), the College Student Innovation and Entrepreneurship Training Program Project of Southwest Minzu University (No: X202210656418); the National Natural Science Foundation of China (Nos. 82173695, 82003609), Guangdong Basic and Applied Basic Research Foundation (Nos. 2020B1515020033, 2020A1515110415, 2020A1515110453).

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

References

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Received: 2022-10-19
Accepted: 2022-11-07
Published Online: 2022-11-21
Published in Print: 2023-01-27

© 2022 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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