Home Crystal structure of (20R)-20,25-epoxy-dammaran-3,12-dione, C30H48O3
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Crystal structure of (20R)-20,25-epoxy-dammaran-3,12-dione, C30H48O3

  • Jian-Qiang Deng , Xiao-Dong Mu , Ruo-Lin Zhao , Zhi Liu , Hang-Jun Tang , Meng He and Qing-Guo Meng EMAIL logo
Published/Copyright: September 29, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 1

Abstract

C30H48O3, orthorhombic, P212121 (no. 19), a = 7.8710(16) Å, b = 13.800(28) Å, c = 24.561(49) Å, V = 2667.9(9) Å3, Z = 4. Rgt(F) = 0.0488, wRref(F2) = 0.1264, T = 293(2) K.

CCDC no.: 1850644

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colorless block
Size:0.24 × 0.20 × 0.18 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.07 mm−1
Diffractometer, scan mode:Bruker P4, ω-scans
θmax, completeness:25.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:36598, 3755, 0.058
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3755
N(param)refined:306
Programs:Bruker programs [1], SHELX [2, 3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.5403(4)0.0979(3)0.93692(15)0.1245(16)
O2−0.2557(2)0.51504(19)0.91667(10)0.0612(7)
O3−0.0353(3)0.81548(16)0.87134(9)0.0503(6)
C10.1790(4)0.2605(2)0.93094(14)0.0466(8)
H1A0.12000.28390.96300.056*
H1B0.09380.23850.90520.056*
C20.2866(5)0.1760(3)0.9469(2)0.0754(12)
H2A0.31140.18220.98540.091*
H2B0.21840.11800.94250.091*
C30.4476(4)0.1598(3)0.91873(14)0.0548(9)
C40.5020(4)0.2195(2)0.86911(13)0.0452(8)
C50.3736(3)0.3029(2)0.85588(12)0.0399(7)
H50.28560.27210.83360.048*
C60.4493(4)0.3811(3)0.81930(13)0.0506(8)
H6A0.53180.41850.83980.061*
H6B0.50770.35090.78900.061*
C70.3111(4)0.4487(3)0.79765(12)0.0493(8)
H7A0.23300.41150.77540.059*
H7B0.36330.49730.77450.059*
C80.2108(3)0.4996(2)0.84292(11)0.0367(7)
C90.1455(3)0.4205(2)0.88304(11)0.0334(6)
H90.06640.38170.86130.040*
C100.2768(3)0.3450(2)0.90543(11)0.0356(7)
C110.0326(4)0.4662(2)0.92820(12)0.0430(7)
H11A−0.01760.41480.94980.052*
H11B0.10320.50510.95210.052*
C12−0.1071(3)0.5289(2)0.90503(12)0.0391(7)
C13−0.0461(3)0.6048(2)0.86643(11)0.0353(6)
H130.03830.64370.88600.042*
C140.0494(3)0.5526(2)0.81925(11)0.0364(7)
C150.0773(4)0.6385(2)0.78049(12)0.0467(8)
H15A0.17120.67840.79280.056*
H15B0.10110.61600.74390.056*
C16−0.0903(4)0.6955(3)0.78222(12)0.0502(8)
H16A−0.16620.67350.75360.060*
H16B−0.06910.76410.77720.060*
C17−0.1706(3)0.6763(2)0.83944(12)0.0408(7)
H17−0.28020.64380.83440.049*
C180.3301(3)0.5741(2)0.87046(14)0.0474(8)
H18A0.44150.54660.87420.071*
H18B0.28640.59050.90580.071*
H18C0.33640.63150.84850.071*
C190.3944(4)0.3878(2)0.94956(12)0.0450(8)
H19A0.32680.41670.97780.068*
H19B0.46650.43610.93360.068*
H19C0.46310.33710.96480.068*
C20−0.1998(4)0.7701(2)0.87181(12)0.0430(7)
C21−0.3336(4)0.8320(3)0.84224(16)0.0644(10)
H21A−0.36860.88430.86550.097*
H21B−0.43030.79250.83350.097*
H21C−0.28560.85780.80940.097*
C22−0.2601(5)0.7509(3)0.92976(13)0.0587(9)
H22A−0.37800.73060.92890.070*
H22B−0.19380.69860.94530.070*
C23−0.2436(6)0.8396(3)0.96542(15)0.0798(13)
H23A−0.31380.89160.95130.096*
H23B−0.28080.82481.00210.096*
C24−0.0601(7)0.8700(3)0.96583(17)0.0900(15)
H24A0.00780.81840.98150.108*
H24B−0.04750.92680.98870.108*
C250.0072(5)0.8932(3)0.90871(18)0.0675(11)
C260.2010(5)0.8927(4)0.9069(3)0.110(2)
H26A0.24200.82900.91550.166*
H26B0.24440.93820.93300.166*
H26C0.23850.91060.87110.166*
C27−0.0591(6)0.9906(3)0.8879(2)0.0827(13)
H27A−0.02690.99880.85040.124*
H27B−0.01131.04210.90920.124*
H27C−0.18070.99210.89080.124*
C280.5037(5)0.1462(3)0.82144(15)0.0714(12)
H28A0.53360.17910.78840.107*
H28B0.39310.11770.81760.107*
H28C0.58560.09630.82870.107*
C290.6855(4)0.2542(3)0.8783(2)0.0782(13)
H29A0.68610.30550.90470.117*
H29B0.73170.27750.84460.117*
H29C0.75330.20120.89130.117*
C30−0.0752(4)0.4815(3)0.79038(13)0.0520(9)
H30A−0.17040.51700.77630.078*
H30B−0.11440.43400.81600.078*
H30C−0.01750.44960.76100.078*

Source of material

(20R)-20,25-Epoxy-dammaran-3,12-dione {systematic name: (8R,9R,10R,13R,14R,17S)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)tetradecahydro-3H-cyclopenta[a]phenanthrene-3,12(2H)-dione)} is synthesized by two-step oxidation reaction in turn.

3-oxo-20(R)-panaxadiol was synthesized by Wu’s method [4]. A solution of (20R)-panaxadiol in CH2Cl2 and pyridinium chlorochromate was stirred for 6 h at room temperature. The solvent was removed under reduced pressure to give a white solid. The white solid was dissolved in ethyl ether and washed with NaHCO3, dried (MgSO4) and concentrated under reduced pressure to give the crude product. The crude products were chromatographied using silica gel and eluted with [petroleum ether-EtOAc (8:1)] to give the pure product. (20R)-20,25-Epoxy-dammaran-3,12-dione is synthesized by reacting 3-oxo-20(R)-panaxadiol with DDQ in 1,4-dioxane at 110 °C temperature heating under reflux for 3 h. The mixture was concentrated in vacuo. The residue was dissolved in water and extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4. The residue was separated by silica column chromatography [petroleum ether-EtOAc (8:1)] to give a white solid. (m.p.: 255–257 °C). Analysis calcd. for C30H48O3: 456.36035; found: MS (ES+): m/z 457.36740 (M + 1).

Experimental details

All H atoms were included in calculated positions and refined as riding atoms, with C—H = 0.96–0.97 Å, with Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for all other H atoms. The absolute configuration was derived from the synthesis and the configuration of the educts.

Discussion

Panaxadiol (PD), one of the protopanaxadiol-type of ginsenoside with a dammarane skeleton can be obtained by acid hydrolysate. It has been reported to exhibits pharmacological activities, such as anti-tumor, anti-HIV and regulating cell cycle and apoptosis [5], [6], [7], [8]. Because of its wide biological properties and its potential medicinal value, the extraction, synthesis and biological activity of panaxadiol and its derivatives have attracted much attention. In this paper, we report the crystal structure of the title compound, whose partial synthesis methods have been reported in other journals [4].

In the molecule of the title compound, bond lengths and angles within the five-membered rings are very similar to those given in the literature for panaxadiol [9], [10], [11], [12], [13].

The structure of the title compound and panaxadiol are equivalent except for the substituents at C(3) and C(6). Two carbon-oxygen double bond exist in the compound which was synthesized by two-step oxidation reaction. Both the first ring and the third ring contain a carbon-oxygen double bond. The C—O bond distance (C3—O1) is 1.208(6) Å, The C—O bond distance (C12—O2) is 1.218(4) Å. The distance of C—O Bond (C20—O3) in Tetrahydropyran Ring is 1.438(4) Å and the distance of C—O Bond (C25—O3) is 1.452(5) Å. The C25—O3—C20—C22, O1—C3—C2—C1, O1—C3—C4—C28 and O2—C12—C11—C9 torsion angles are 43.1(4)°, 170.9(4)°, 68.3(4)° and 125.0(3)°, respectively. The C25—O3—C20—C22 torsion angle indicates that the C20 position is R-form.

Acknowledgements

X-ray data were collected at School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, 252000, People’s Republic of China. This work was supported by the National Natural Science Foundation of China [No. 81473104] and Shandong graduate education innovation program [SDYY16132].

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Received: 2018-07-13
Accepted: 2018-09-15
Published Online: 2018-09-29
Published in Print: 2018-12-19

©2018 Jian-Qiang Deng et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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  52. Crystal structure of (20R)-20,25-epoxy-dammaran-3,12-dione, C30H48O3
  53. Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-((pyridin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C32H31N5O2
  54. The crystal structure of 2-(4-fluorophenyl)-1,3,4-oxadiazole, C8H5FN2O
  55. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(tri(p-tolyl)phosphine-κP)copper(I) tetrafluoroborate – 4,4′-bipyridine (2/1), C57H54BCuF4N3P2
  56. The crystal structure of 2,6-dimethyl-3,5-dinitrocyclohexa-2,5-diene-1,4-dione, C8H6N2O6
  57. The crystal structure of 2,3-dimethyl-1,4-dinitrobenzene – a Z′ = 4 structure, C8H8N2O4
  58. Crystal structure of [(1,2-η)-1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl] (1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-κ6N2,O4) rubidium (I), [Rb(diaza-18-crown-6)]Cp*, C22H41N2O4Rb
  59. Crystal structure of 2-(4-fluorophenyl)-N-phenyl-2-(phenylamino)ethanesulfonamide – toluene (1/0.5), C23.5H23FN2O2S
  60. Crystal structure of pyrene-4-aldehyde, C17H10O
  61. Crystal structure of 2-(furan-2-yl)-5-methyl-1,3-dioxane-5-carboxylic acid, C10H12O5
  62. Crystal structure of 2-(4-chlorophenyl)-3-phenyl-1,8-naphthyridine, C20H13N2Cl
  63. Crystal structure and photochromism of 1-(2-ethyl-5-formylthiophen-3yl)-2-(2-cyano-1,5-dimethyl-4-pyrrl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C19H14F6N2OS
  64. Crystal structure of 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16BrIN2
  65. Crystal structure of 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O
  66. Crystal structure of 4-(acetoxymethyl)-6-(3-acetyl-3-(4-fluorophenyl)thioureido)cyclohex-4-ene-1,2,3-triyl triacetate, C24H26FN2O9S
https://doi.org/10.1515/ncrs-2018-0237
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of bis(6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2,4-diiodophenolato)-κ4N,N′,O,O′)cer(IV), C32H20CeI8N4O4
  3. Crystal structure of (6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato-κ2N,O))copper(II), C16H12Cl2CuN2O2
  4. Crystal structure of poly[aqua-(μ3-4-(pyridin-4-yl)isophthalato-κ4O,O′:O′′:O′′′)-(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:O′)samarium(III)], C26H18N2O9Sm
  5. Crystal structure of 1-{4-[(2-hydroxy-5-nitrobenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15N3O4
  6. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-bis(μ2-1-(8-(2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)naphthalen-2-olato-κ6O:O,N,N′,O′:O′)trizinc(II), C44H38Zn3N4O12
  7. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)–bis(μ2–(8-(2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)naphthalen-2-olato-κ6O:O,N,N′,O′:O′)tricobalt(II), C44H38Co3N4O12
  8. Crystal structure of poly[aqua(μ4-2,2′,2′′-nitrilotriacetato-κ6O1,O3,O5:O2:O4:O6)-yttrium(III)], C6H8NO7Y
  9. Crystal structure of catena-poly[bromido-(μ2-pyrazine-2-carboxylato-κ3N:N′,O)copper(II)], C10H6N4Cu2O4Br
  10. Crystal structure of poly[dodekais(μ2-2,6-difluorobenzoato-κ2O:O′)-bis((μ3-hexamethylenetetramine-κ3N:N′:N′′)hexacopper(II)], C48H30N4O12F12Cu3
  11. Crystal structure of methyl 4-(4-hydroxy-3-nitrophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H18N2O6
  12. Crystal structure of N-phenyl-2-(propan-2-ylidene)hydrazine-1-carbothioamide, C10H13N3S
  13. Crystal structure of sodium caesium zinc phosphate, NaCsZnP2O7
  14. Crystal structure of methyl 4-(4-isopropylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C23H29NO3
  15. Crystal structure of catena-poly[bis(μ2-1,3-di(4H-1,2,4-triazol-4-yl)benzene-κ2N:N′)-bis(thiocyanato-κ1N)cobalt(II), C22H16CoN14S2
  16. Crystal structure of catena-poly[(μ2-2,5-di(pyridin-3-yl)-1,3,4-thiadiazole-κ2N:N′)-bis(2,5-di(pyridin-3-yl)-1,3,4-thiadiazole-κ1N)-bis(thiocyanato-κ1N)cobalt(II)], C38H24CoN14S5
  17. Crystal structure of bis(2,5-di(pyridin-2-yl)-1,3,4-thiadiazole-κ2N,N′)-bis(thiocyanato-κ1N)cobalt(II), C26H16CoN10S4
  18. Crystal structure of (bis((1H-benzo[d]imidazol2-yl)methyl)amine-κ3N,N′,N′′)-(pyridine-2,6-dicarboxylato-κ3N,O,O′)zinc(II) — methanol — water (1/2/1), C25H28N6O7Zn
  19. Crystal structure of catena-poly[triaqua-(μ2-5-methoxy-isophthalato-κ2O:O′)copper(II)], C9H12CuO8
  20. Structure and photochromism of 1-[2-methyl-5-phenyl-3-thienyl]-2-[2-methyl-5-(4-chlorophenyl)-3-thienyl]3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16ClF6S2
  21. Crystal structure of methyl 4-(3-phenoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C26H27NO4
  22. Crystal structure of poly[diaqua-di-μ2-hydroxido-(μ4-3,4,5,6-tetrafluoro-1,2-phthalato-κ4O:O′:O′′:O′′′)-(μ4-3,4,5,6-tetrafluoro-1,2-phthalato-κ5O,O:O′:O′′:O′′′)disamarium(III)] – bipyridine (2/1), C21H11NF16O12Sm2
  23. Crystal structural of diethyl 4-(3,5-dibromo-4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, C19H21Br2NO5
  24. Crystal structure of catena-poly[tetraaqua(μ2-4-(1H-imidazol-1-yl)pyridine-κ2N:N′))zinc(II)] thiophene-2,5-dicarboxylate, C14H17N3O8ZnS
  25. Crystal structure of (20S)-20-(dimethylamino)-3-(tigloylamino)-5α-pregn-2,16-dien-4-one, C28H42N2O2
  26. Crystal structure of rac-trans-N,N′-bis(3,5-diiodosalicylidene)-1,2-cyclohexanediamine, C20H18I4N2O2
  27. Crystal structure of 2-bromo-7-(4-(dimethylamino)phenyl)-10-methylacridin-9 (10H)-one, C22H19BrN2O
  28. Crystal structure of catena-poly[(μ2-pentane-1,5-dicarboxylato-κ2O:O′)-(μ2-2-[(1H-imidazol-1-yl)methyl]-6-methyl-1H-benzimidazole-κ2N:N′)zinc(II)] sesquihydrate, C17H21N4O5.5Zn
  29. Crystal structure of ethyl 2-amino-4-(3,4-difluorophenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C21H15F2NO5
  30. Crystal structure of 9-(5-methylthiophen-2-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione, C18H18O3S
  31. Crystal structure of [5,5′-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-2-ylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido)-κ4N,N′,N′′,N′′′]nickel(II), C23H30N4O4Ni
  32. Crystal structure of (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazineyl) terephthalic acid-dimethylsulfoxide (1/1), C18H15N3O6 ⋅ C2H6OS
  33. Crystal structure of (2E,4Z)-dimethyl 4-((phenylamino)methylene)pent-2-enedioate, C14H15N1O4
  34. Crystal structure of (2Z,2′Z)-1,1′-(pyridine-2,6-diyl) bis(3-hydroxy-3-phenylprop-2-en-1-one), C23H17NO4
  35. Crystal structure of ethyl 2-amino-4-(3-bromophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C21H16BrNO5
  36. Crystal structure of bis(μ2-3,5-dichloro-2-oxidobenzoato-κ4O,O′:O′,O′′)-hexakis(μ2-pivalato-κ2O:O′)-bis(pivalato-κ2O,O′)-tetrakis(1,10-phenanthroline-κ2N,N′)tetragadolinium(III), C102H108Cl4Gd4N8O22
  37. Crystal structure of catena-poly[aqua-bis(formato-κ1O)-(μ2-1,1′-(oxybis(1,4-phenylene))-bis(1H-1,2,4-triazole)-κ2N:N′)copper(II)]hydrate, C18H16CuN6O6
  38. Crystal structure of 5-bromo-2-(naphthalen-6-yl)pyridine, C15H10BrN
  39. Crystal structure of N-(4-methoxybenzyl)pyridazin-3-amine- a rare Z′ = 4 structure, C12H13N3O
  40. Crystal structure of bis(perchlorato-κ1O)-bis(3,4,5-trimethoxy-N-(pyridin-2-yl)benzamide-κ2N,O)copper(II), C32H30Cl2CuN4O16
  41. Crystal structure of methyl 4-methyl-2,5-di(pyridin-4-yl)-1H-pyrrole-3-carboxylate monohydrate C17H15N3O2⋅H2O
  42. Crystal structure of dimethyl 5-(10-(methoxycarbonyl)anthracen-9-yl) isophthalate,C26H20O6
  43. Crystal structure of tert-butyl (R)-(1-(benzylamino)-3-methoxy-1-oxopropan-2-yl)carbamate, C16H24N2O4
  44. Crystal structure of aqua-bis(1,5-dimethyl-2-phenyl-4-(((E)-4-pyridylmethylene)amino)pyrazolidin-3-one-κN)-(nitrato-κO)-(nitrato-κ2O,O′)zinc(II), C34H34N10O9Zn
  45. Crystal structure of catena-poly[dichlorido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)cobalt(II)] – methanol (1/1), C18H20Cl2CoN4O2
  46. Crystal structure of poly[diaqua-bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′)manganese(II)]bis(2-carboxybenzoate) dihydrate, MnC40H40N10O12
  47. The crystal structure of 4-((3,4-dichlorobenzylidene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one, C18H15Cl2N3O
  48. Crystal structure of bis(2-methoxy-6-((2-(pyrimidin-2-yl)hydrazono)methyl)phenolato-κ3N,N′,O)iron(III) perchlorate, C24H22N8O8ClFe
  49. The crystal structure of 2-[4-hydroxy-3-methoxyphenyl]-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl, C14H19N2O4
  50. Crystal structure of diaqua-bis(3,3-dimethylacrylato-κ2O,O′)zinc(II), C10H18ZnO6
  51. Crystal structure of dichloro-tetrakis[(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol-κN]cadmium (II), C60H74CdCl6N12O4
  52. Crystal structure of (20R)-20,25-epoxy-dammaran-3,12-dione, C30H48O3
  53. Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-((pyridin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C32H31N5O2
  54. The crystal structure of 2-(4-fluorophenyl)-1,3,4-oxadiazole, C8H5FN2O
  55. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(tri(p-tolyl)phosphine-κP)copper(I) tetrafluoroborate – 4,4′-bipyridine (2/1), C57H54BCuF4N3P2
  56. The crystal structure of 2,6-dimethyl-3,5-dinitrocyclohexa-2,5-diene-1,4-dione, C8H6N2O6
  57. The crystal structure of 2,3-dimethyl-1,4-dinitrobenzene – a Z′ = 4 structure, C8H8N2O4
  58. Crystal structure of [(1,2-η)-1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl] (1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-κ6N2,O4) rubidium (I), [Rb(diaza-18-crown-6)]Cp*, C22H41N2O4Rb
  59. Crystal structure of 2-(4-fluorophenyl)-N-phenyl-2-(phenylamino)ethanesulfonamide – toluene (1/0.5), C23.5H23FN2O2S
  60. Crystal structure of pyrene-4-aldehyde, C17H10O
  61. Crystal structure of 2-(furan-2-yl)-5-methyl-1,3-dioxane-5-carboxylic acid, C10H12O5
  62. Crystal structure of 2-(4-chlorophenyl)-3-phenyl-1,8-naphthyridine, C20H13N2Cl
  63. Crystal structure and photochromism of 1-(2-ethyl-5-formylthiophen-3yl)-2-(2-cyano-1,5-dimethyl-4-pyrrl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C19H14F6N2OS
  64. Crystal structure of 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16BrIN2
  65. Crystal structure of 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O
  66. Crystal structure of 4-(acetoxymethyl)-6-(3-acetyl-3-(4-fluorophenyl)thioureido)cyclohex-4-ene-1,2,3-triyl triacetate, C24H26FN2O9S
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