Home Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α] phenanthren-3-one O-(4-fluorobenzoyl) oxime, C28H36FNO2
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Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α] phenanthren-3-one O-(4-fluorobenzoyl) oxime, C28H36FNO2

  • Lan Yue ORCID logo , Peng Wei , Jiang-Hei Ye , Kang He EMAIL logo and Juan Zou EMAIL logo
Published/Copyright: August 7, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 5

Abstract

C28H36FNO2, orthorhombic, P212121 (no. 19), a = 6.3277(3) Å, b = 11.9665(19) Å, c = 32.2419(19) Å, V = 2441.4(2) Å3, Z = 4, Rgt(F) = 0.0537, wRref(F2) = 0.1403, T = 273(2) K.

CCDC no.: 2267280

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 acicular
Size: 0.24 × 0.21 × 0.19 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 30.5°, 99 %
N(hkl)measured, N(hkl)unique, Rint: 25,486, 7310, 0.031
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 4962
N(param)refined: 292
Programs: Olex2 [1], Bruker [2], Shelx [3], Diamond [4]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.9196 (4) 0.4783 (2) 0.35688 (7) 0.0514 (5)
C2 0.9218 (5) 0.4837 (2) 0.30932 (8) 0.0602 (6)
C3 0.9845 (4) 0.5975 (2) 0.29536 (7) 0.0530 (6)
C4 1.1819 (4) 0.6450 (2) 0.31454 (8) 0.0562 (6)
C5 1.1725 (3) 0.63710 (18) 0.36190 (7) 0.0442 (5)
C6 1.3681 (4) 0.6879 (2) 0.38203 (8) 0.0538 (6)
C7 1.3490 (4) 0.6885 (2) 0.42901 (8) 0.0557 (6)
C8 1.2914 (3) 0.57491 (18) 0.44739 (7) 0.0446 (5)
C9 1.0962 (3) 0.52526 (17) 0.42520 (7) 0.0416 (4)
C10 1.1264 (3) 0.51760 (18) 0.37777 (7) 0.0431 (5)
C11 1.0227 (5) 0.4165 (2) 0.44625 (8) 0.0617 (7)
C12 0.9927 (5) 0.4267 (2) 0.49317 (8) 0.0622 (7)
C13 1.1907 (4) 0.47127 (17) 0.51481 (7) 0.0481 (5)
C14 1.2449 (4) 0.58310 (17) 0.49352 (7) 0.0457 (5)
C15 1.4066 (5) 0.6365 (2) 0.52233 (8) 0.0661 (7)
C16 1.3313 (5) 0.6027 (2) 0.56567 (8) 0.0645 (7)
C17 1.1739 (4) 0.5085 (2) 0.55982 (7) 0.0538 (6)
C18 1.3708 (5) 0.3855 (2) 0.51245 (10) 0.0752 (8)
C19 1.3036 (4) 0.4348 (2) 0.36666 (8) 0.0595 (6)
C20 1.0548 (5) 0.4710 (3) 0.59052 (8) 0.0699 (7)
C21 0.9040 (7) 0.3750 (3) 0.59090 (10) 0.1025 (13)
C22 0.5893 (4) 0.6732 (2) 0.22840 (7) 0.0555 (6)
C23 0.4051 (4) 0.6114 (2) 0.21149 (7) 0.0514 (5)
C24 0.3678 (4) 0.4993 (2) 0.21947 (8) 0.0606 (6)
C25 0.1899 (5) 0.4472 (2) 0.20411 (9) 0.0691 (7)
C26 0.0536 (4) 0.5090 (3) 0.18063 (9) 0.0695 (7)
C27 0.0821 (5) 0.6186 (3) 0.17211 (9) 0.0729 (8)
C28 0.2613 (5) 0.6705 (2) 0.18770 (8) 0.0639 (7)
F1 −0.1238 (3) 0.45766 (19) 0.16570 (7) 0.1027 (7)
H1 0.948872 0.319961 0.571098 0.154*
H2 0.463689 0.458905 0.235360 0.073*
H3 0.782414 0.465960 0.298667 0.072*
H4 1.020683 0.429066 0.298516 0.072*
H5 1.304064 0.604193 0.304480 0.067*
H6 1.197399 0.722555 0.306375 0.067*
H7 1.386610 0.763851 0.372159 0.065*
H8 1.491843 0.645183 0.374031 0.065*
H9 1.482293 0.712894 0.440797 0.067*
H10 1.241924 0.742449 0.436972 0.067*
H11 1.411081 0.524037 0.443408 0.053*
H12 1.066586 0.509862 0.615386 0.084*
H13 0.765190 0.400996 0.583749 0.154*
H14 0.901044 0.342295 0.618079 0.154*
H16 1.264651 0.665532 0.579450 0.077*
H16A 1.449644 0.577780 0.582408 0.077*
H17 1.547409 0.607969 0.516872 0.079*
H18A 1.407593 0.717125 0.519243 0.079*
H18 1.496313 0.416689 0.524520 0.113*
H19 0.957839 0.353842 0.504471 0.075*
H20 0.875178 0.476442 0.498774 0.075*
H21 0.890026 0.393338 0.433892 0.074*
H22 1.125974 0.358431 0.440748 0.074*
H23 0.981765 0.579215 0.429515 0.050*
H24 1.331328 0.319262 0.527378 0.113*
H26 1.397476 0.366775 0.483966 0.113*
H27 1.117362 0.629160 0.495841 0.055*
H28 1.052634 0.683334 0.370616 0.053*
H29 1.261746 0.360589 0.374475 0.089*
H30 1.329348 0.437196 0.337331 0.089*
H31 1.430331 0.454837 0.381245 0.089*
H32 0.891741 0.401825 0.365246 0.062*
H33 0.804043 0.524048 0.367015 0.062*
H34 −0.015512 0.657996 0.156273 0.087*
H35 0.284985 0.745744 0.182122 0.077*
H36 0.163596 0.372129 0.209571 0.083*
N1 0.8902 (3) 0.66255 (18) 0.27029 (6) 0.0569 (5)
O1 0.7034 (3) 0.60700 (15) 0.25381 (5) 0.0601 (4)
O2 0.6295 (4) 0.76855 (17) 0.22116 (7) 0.0844 (7)

1 Source of material

The (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexade-cahydro-3H-cyclopenta[α]phenanthren-3-one oxime (1 mmol) was dissolved in 6 ml of benzene and stired at room temperature. After the addition of 1.5 mmol of triethylamine, we added benzene solution containing 1.5 mmol 4-fluorobenzoyl chloride within 3 min, after continuing the reaction at room temperature for 1.5 h, we added water to quench the reaction. Extracted with ethyl acetate for three times, gave an organic phase, which was dried by anhydrous Na2SO4, concentrated under reduced pressure, and purified by silica gel chromatography. Some colorless needle crystals were obtained 80 % yield.

2 Comment

Steroidal alkaloids, known for their anti-cancer, antibiosis, and cholinesterase inhibition effects [5], [6], [7], are the characteristic active components found in Sarcococca. Our previous research focused on studying the chemical constituents of Sarcococca ruscifolia and Sarcococca hookeriana, resulting in the discovery of several new pregnane alkaloids that exhibited significant anti-tumor activity [8], [9], [10]. However, due to the limited structural diversity of natural pregnane alkaloids, we sought to enhance the structural diversity of steroidal alkaloids by synthesizing a series of pregnane alkaloid derivatives derived from epiandrosterone [11], [12], [13], [14]. In our ongoing efforts to synthesize additional compounds, we incorporated a substituted 4-fluorobenzoyl chloride, aiming to identify a new compound with potential biological activity.

The title compound contains three six-membered rings, a five-membered ring, three methyl groups, a carbon-carbon double bond, a carbon-nitrogen double bond, a benzene ring, a group, and atomic methyl substituents C10 and C13 are β configurations. The phenyl ring and the CO2N group in the compound are in a plane. Typical distanes are: d (C3–N1) = 1.271(3) Å, d(C22–O2) = 1.192(3) Å, d(C26–F1) = 1.368(3) Å. The five-and six-membered ring structures show molecular interactions only through van der Waals forces.

Corresponding authors: Kang He and Juan Zou, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, P.R. China, E-mail: ,

Funding source: Key Projects of Guizhou Basic Research Program

Award Identifier / Grant number: Qiankehejichu–ZK (2022) key 046

Funding source: Natural–Scientific Research Program of Department of Education of Guizhou Province??Qianjiaoji

Award Identifier / Grant number: (2023)070

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

  2. Research funding: This work was funded by Key Projects of Guizhou Basic Research Program [grant number Qiankehejichu-ZK (2022) key 046], the Natural-Scientific Research Program of Department of Education of Guizhou Province Qianjiaoji [(2023)070].

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

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Received: 2023-06-19
Accepted: 2023-07-28
Published Online: 2023-08-07
Published in Print: 2023-10-26

© 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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  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
https://doi.org/10.1515/ncrs-2023-0290
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of (N-([1,1′:4′,1″-terphenyl]-4,4′-diethyl)-2-(bis(pyridin-2-ylmethyl)amino)acetamide-κ4N,N,N″, O)tri(nitrato-kO, O′) samarium(III) - methanol - acetonitrile (1/1/1), C40H39SmN8O14
  4. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(2-chloro-4-methyl phenolate-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV), C27H27Cl2N3O6Ti
  5. N′-[(1E)-(4–Fluorophenyl)methylidene]adamantane-1-carbohydrazide, C18H21FN2O
  6. Crystal structure of 4-bromo-3-nitro-1H-pyrazole-5-carboxylic acid monohydrate, C4H2N3BrO4·H2O
  7. Crystal structure of dipyridine-k1N-tris(2,2,6,6-tetramethyl-5-oxohept-3-en-3-olato-k2O,O′)dysprosium(III), DyC43H67O6N2
  8. Crystal structure of cyclo[tetraiodido-bis{μ2-1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-isopropyl-imidazol)-k2N:N}dicadmiun(II)], C26H30N10Cd2I4
  9. The crystal structure of tert-butyl (E)-3-(2-(benzylideneamino)phenyl)-1H-indole-1-carboxylate, C26H24N2O2
  10. The crystal structure of 4-(3-carboxy-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4- dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 2,5-dihydroxybenzoate methanol solvate, C27H32FN3O9
  11. Crystal structure of (μ2-1-(4,4′-bipyridine-κ2N:N′)-bis[diaqua-(4-iodopyridine-2,6-dicarboxylato-κ3O,N,O′)–cobalt(II)], C24H20Co2I2N4O12
  12. The crystal structure of dimethyl 4,4′-(10,20-diphenylporphyrin-5,15-diyl)dibenzoate dichloromethane solvate, C49H36N4O4Cl2
  13. (E)-2-((E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ylidene)hydrazine-1-carbothioamide C14H23N3S1
  14. The crystal structure of [1-(4-(trifluoromethyl)phenyl)-3,4-dihydroquinolin-2(1H)-one], C16H12F3NO
  15. Crystal structure of (E)-2-amino-N′-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)benzohydrazide – dimethylformamide – water (1/1/2), C15H16N4O3·C3H7NO·2H2O
  16. Crystal structure of 3-(4-bromophenyl)-5-methyl-1H-pyrazole, C10H9BrN2
  17. Crystal structure of 1,10-phenanthrolinium bromide dihydrate, C12H9N2Br
  18. Crystal structure of N-(4′-chloro-[1,1′-biphenyl]-2-yl)formamide, C13H10ClNO
  19. The crystal structure of nitroterephthalic acid, C8H5NO6
  20. Crystal structure of (2-((4-bromo-2,6-dichlorophenyl)amino)phenyl) (morpholino)methanone, C17H15BrCl2N2O2
  21. Crystal structure of tetraaqua-bis(ethanol-κO)-tetrakis(μ2-trifluoroacetate-κ2O:O′)-bis(trifluoroacetate-κ2O)digadolinium(III) Gd2C16H20O18F18
  22. The crystal structure of dimethyl 4,4′-[10,20-bis(2,6-difluorophenyl)porphyrin-5,15-diyl]dibenzoate chloroform solvate, C50H32Cl6F4N4O4
  23. The crystal structure of N,N′-((nitroazanediyl)bis(methylene))diacetamide, C6H12O4N4
  24. The crystal structure of [bis(2,2′-bipyridine-6-carboxylato-κ3N,N,O)magnesium(II)]dihydrate, C22H18N4O6Mg
  25. Crystal structure of poly[diaqua-(bis(μ2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′] cobalt(II)-tetraqua-bis(1,4-bis(imidazol-1-ylmethyl)benzene)-κ1N)-cobalt(II) di(2,5-thiophenedicarboxylate) dihydrate, C68H76Co2N16O16S2
  26. Crystal structure of poly[chlorido-μ2-chlorido-(μ2-1-[(2-ethyl-4-methyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κN:N’)cadmium(II)], C13H15CdN5Cl2
  27. The crystal structure of (4-hydroxybenzenesulfonate)-k1O-6,6′-((1E,1′E)- (ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene)) bis(2-methoxyphenol)-κ2N,N,μ2O,O,κ2O, O)-(methanol)-cobalt(II) sodium(I), C25H27CoN2NaO9S
  28. Crystal structure of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)(4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)methanone, C17H18F6N6O
  29. Crystal structure of bis{[(cyclohexylimino)(phenylimino)-l5-(methyl)diethylazane-κ2N:N′]-(ethyl)-zinc(II)]}, C38H62N6Zn2
  30. Crystal structure of 2-[(4-bromobenzyl)thio]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C13H8Br2N2OS2
  31. Crystal structure of 10-methoxy-7,11b,12,13-tetrahydro-6H-pyrazino [2′,3′:5,6]pyrazino[2,1-a]isoquinoline, C15H16N4O
  32. The crystal structure of 1-propyl-2-nitro-imidazole oxide, C6H9N3O3
  33. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid–2-ethoxybenzamide (1/1), C17H16N2O8
  34. The structure of RUB-1, (C8H16N)6[B6Si48O108], a boron containing levyne-type zeolite, occluding N-methyl-quinuclidinium in the cage-like pores
  35. The crystal structure of diaqua-(naphthalene-4,5-dicarboxylate-1,8-dicarboxylic anhydride-κ1O)-(4′-(4-(1H-benzimidazolyl-1-yl)phenyl)-2,2′:6′,2″-terpyridine-κ3N,N′,N″)–manganese(II) dihydrate, C42H27MnN5O9·2H2O
  36. Crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene))bis (3-(3-bromopropoxy)phenol), C20H22Br2N2O4
  37. The crystal structure of 3-(2-hydroxyphenyl)-4-phenyl-6-(p-tolyl)-2H-pyran-2-one, C24H18O3
  38. Crystal structure of bis(μ2-2-(1,5-dimethyl–3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)-(nitrato-κ2O,O′)dicobalt(II), C36H32Co2N8O4
  39. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α] phenanthren-3-one O-(4-fluorobenzoyl) oxime, C28H36FNO2
  40. The crystal structure of 4-aminiumbiphenyl benzenesulfonate, C18H17NO3S
  41. Synthesis and crystal structure of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate, C18H17N3O9
  42. Crystal structure of N-(Ar)-N′-(Ar′)-formamidine, C14H12Br2N2O
  43. The crystal structure of 4-(2,4-dichlorophenyl)-2-(4-fluorophenyl)-5-methyl-1H-imidazole, C16H11Cl2FN2
  44. Crystal structure of 1-(4–chlorophenyl)-4-benzoyl-3-methyl-1H-pyrazol-5-ol, C17H13ClN2O2
  45. The crystal structure of 5-amino-1-methyl-4-nitroimidazole, C4H6O2N4
  46. Crystal structure of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene-N,N′-bis(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-1,3,2-diazaborol-2-yl)-l2-germenediamine, C63H94B2GeN8
  47. The crystal structure of (bromido, chlorido)-tricarbonyl-(5,5′-dimethyl-2,2′-bipyridine)-rhenium(I), C15H12Br0.2Cl0.8N2O3Re1
  48. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
  49. The crystal structure of poly[2-(4-carboxypyridin-3-yl)terephthalpoly[diaqua-(μ4-2-(6-carboxylatopyridin-3-yl)terephthalato-κ5O,N:O′:O″,O‴)]) cadmium(II)] dihydrate, C28H20Cd3N2O16
  50. Crystal structure of [tetraaqua-bis((3-carboxy-5-(pyridin-4-yl)benzoate-κ1N)cobalt(II)] tetrahydrate, C26H32CoN2O16
  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
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