Startseite Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene-1(6bH)-one, C30H48O2
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Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene-1(6bH)-one, C30H48O2

  • Kang He , Lin-Lin Fan , Tian-Tai Wu , Qi-Long Zhang und Juan Zou EMAIL logo
Veröffentlicht/Copyright: 24. Mai 2019

Abstract

C30H48O2, orthorhombic, P212121 (no. 19), a = 10.8192(12) Å, b = 16.4915(17) Å, c = 28.832(3) Å, V = 5144.4(10) Å3, Z = 4, Rgt(F) = 0.0582, wRref(F2) = 0.1169, T = 293(2) K.

CCDC no.: 1914113

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:0.24 × 0.23 × 0.21 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.07 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:39401, 9050, 0.071
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5738
N(param)refined:581
Programs:Bruker [1], SHELX [2], [3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
C1′0.1559(4)0.4989(2)0.88140(14)0.0488(11)
H1′A0.07920.52260.87050.059*
H1′B0.17240.52070.91200.059*
C10.1376(4)0.3195(2)1.11456(15)0.0543(12)
H1A0.14100.33581.14690.065*
H1B0.06400.34341.10110.065*
C20.1266(5)0.2274(3)1.11219(17)0.0675(14)
H2A0.19590.20291.12830.081*
H2B0.05120.21041.12760.081*
C2′0.1393(5)0.4068(2)0.88525(15)0.0613(13)
H2′A0.21250.38320.89920.074*
H2′B0.06940.39510.90520.074*
C3′0.1182(4)0.3693(3)0.83825(15)0.0535(12)
H3′A0.03990.38860.82620.064*
H3′B0.11200.31100.84190.064*
C30.1249(4)0.1983(3)1.06231(17)0.0639(14)
H3A0.05040.21831.04750.077*
H3B0.12120.13951.06220.077*
C40.2373(4)0.2255(3)1.03366(16)0.0524(12)
C4′0.2192(4)0.3879(2)0.80295(14)0.0406(11)
C50.2504(4)0.3186(2)1.03907(13)0.0392(10)
H50.17420.34031.02560.047*
C5′0.2393(4)0.4812(2)0.80135(12)0.0345(10)
H5′0.16010.50280.79040.041*
C6′0.3327(4)0.5107(2)0.76547(13)0.0402(10)
H6′A0.41580.50150.77680.048*
H6′B0.32250.48030.73690.048*
C60.3527(4)0.3560(2)1.00992(14)0.0438(11)
H6A0.43200.34521.02440.053*
H6B0.35290.33110.97940.053*
C7′0.3146(4)0.6005(2)0.75584(13)0.0434(11)
H7′A0.23350.60830.74220.052*
H7′B0.37550.61760.73320.052*
C70.3351(4)0.4465(2)1.00500(13)0.0430(11)
H7A0.25920.45650.98800.052*
H7B0.40280.46830.98680.052*
C80.3294(3)0.4919(2)1.05125(13)0.0321(9)
C8′0.3258(3)0.6550(2)0.79896(12)0.0336(10)
C9′0.2478(4)0.6181(2)0.83938(11)0.0320(9)
H9′0.16180.62520.82950.038*
C90.2384(4)0.4474(2)1.08507(12)0.0324(10)
H90.15670.45541.07120.039*
C10′0.2604(4)0.5244(2)0.84876(13)0.0351(10)
C100.2522(4)0.3535(2)1.08924(13)0.0389(10)
C11′0.2590(4)0.6700(2)0.88308(12)0.0422(11)
H11A0.20860.64650.90740.051*
H11B0.34430.66960.89350.051*
C110.2318(4)0.4929(2)1.13164(12)0.0382(10)
H11C0.17260.46601.15170.046*
H11D0.31200.49061.14660.046*
C12′0.2185(4)0.7570(2)0.87486(13)0.0416(11)
H12A0.23440.78870.90260.050*
H12B0.13030.75810.86900.050*
C120.1941(4)0.5811(2)1.12567(13)0.0378(10)
H12C0.19580.60801.15560.045*
H12D0.11020.58361.11390.045*
C13′0.2860(3)0.7952(2)0.83401(12)0.0324(10)
H13′0.37370.79080.84210.039*
C130.2806(3)0.6250(2)1.09223(12)0.0312(10)
H130.36330.61491.10480.037*
C14′0.2728(3)0.7442(2)0.78856(12)0.0329(10)
C140.2818(3)0.5828(2)1.04363(12)0.0310(10)
C15′0.3471(4)0.7859(2)0.74933(14)0.0503(12)
H15A0.43460.78050.75600.060*
H15B0.33100.75770.72040.060*
C150.3694(4)0.6285(2)1.00989(13)0.0418(11)
H15C0.45420.61731.01870.050*
H15D0.35730.60730.97880.050*
C16′0.3171(4)0.8758(2)0.74277(14)0.0543(13)
H16A0.36780.89830.71820.065*
H16B0.23100.88220.73420.065*
C160.3507(4)0.7203(2)1.00882(13)0.0449(11)
H16C0.41050.74500.98820.054*
H16D0.26850.73290.99750.054*
C17′0.3426(4)0.9195(2)0.78781(15)0.0435(11)
H17′0.42840.90670.79590.052*
C170.3669(3)0.7530(2)1.05743(12)0.0343(10)
H170.44700.73281.06830.041*
C180.2703(3)0.7185(2)1.09068(12)0.0304(9)
C18′0.2641(4)0.8871(2)0.82760(13)0.0334(10)
C190.3042(4)0.7598(2)1.13740(13)0.0420(11)
H19C0.23040.77361.15480.050*
H19D0.35570.72461.15620.050*
C19′0.3096(4)0.9387(2)0.86941(15)0.0482(12)
H19A0.24180.95130.89020.058*
H19B0.37330.91030.88660.058*
C200.3628(4)0.8425(2)1.07029(13)0.0378(10)
H200.43430.87071.05710.045*
C20′0.3285(4)1.0114(3)0.79543(17)0.0518(12)
H20′0.38981.04080.77690.062*
C21′0.3617(4)1.0164(3)0.84698(17)0.0625(14)
H21A0.32491.06410.86090.075*
H21B0.45061.01910.85100.075*
C210.3757(4)0.8373(2)1.12298(14)0.0481(11)
H21C0.34020.88491.13770.058*
H21D0.46200.83321.13180.058*
C220.2432(4)0.8821(2)1.05344(15)0.0470(11)
C22′0.1983(4)1.0401(3)0.78307(17)0.0544(13)
C230.2097(5)0.2046(3)0.98266(16)0.0720(16)
H23D0.13800.23390.97260.108*
H23E0.27930.21930.96380.108*
H23F0.19480.14740.97980.108*
C23′0.1731(5)0.3585(3)0.75561(15)0.0678(15)
H23A0.23480.36930.73250.102*
H23B0.15740.30120.75690.102*
H23C0.09820.38650.74770.102*
C24′0.3368(4)0.3397(3)0.81432(16)0.0600(13)
H24A0.39960.35190.79180.090*
H24B0.36550.35430.84470.090*
H24C0.31880.28270.81350.090*
C240.3524(5)0.1768(3)1.04778(19)0.0712(15)
H24D0.42190.19441.02960.107*
H24E0.36940.18561.08010.107*
H24F0.33800.12021.04240.107*
C25′0.3848(4)0.5038(3)0.87230(14)0.0492(11)
H25A0.40920.54790.89200.074*
H25B0.44680.49530.84900.074*
H25C0.37570.45550.89050.074*
C250.3665(4)0.3288(2)1.11789(14)0.0542(12)
H25D0.37720.36601.14310.081*
H25E0.43850.32981.09850.081*
H25F0.35500.27501.12990.081*
C260.4632(3)0.4920(2)1.07159(14)0.0442(11)
H26D0.50110.44031.06610.066*
H26E0.45970.50221.10430.066*
H26F0.51100.53371.05680.066*
C26′0.4646(3)0.6591(2)0.81171(14)0.0465(11)
H26A0.49550.60530.81670.070*
H26B0.47470.69050.83950.070*
H26C0.50950.68420.78680.070*
C27′0.1374(4)0.7410(2)0.77235(13)0.0453(11)
H27A0.08780.71550.79580.068*
H27B0.10780.79510.76700.068*
H27C0.13210.71040.74410.068*
C270.1512(4)0.5847(2)1.02128(13)0.0440(11)
H27D0.09370.55701.04110.066*
H27E0.12540.64001.01740.066*
H27F0.15390.55840.99160.066*
C280.1440(4)0.7518(2)1.07785(13)0.0357(10)
C28′0.1306(4)0.9119(3)0.82084(13)0.0367(10)
C290.2524(5)0.9066(3)1.00260(16)0.0710(15)
H29D0.31980.94380.99870.107*
H29E0.26650.85930.98400.107*
H29F0.17680.93210.99320.107*
C29′0.1835(5)1.0556(3)0.73178(18)0.0843(18)
H29A0.24211.09590.72210.126*
H29B0.19781.00630.71500.126*
H29C0.10121.07460.72570.126*
C30′0.1575(5)1.1150(3)0.80956(19)0.0811(17)
H30A0.21391.15870.80350.122*
H30B0.07601.13030.79980.122*
H30C0.15691.10340.84220.122*
C300.2021(4)0.9546(3)1.08161(19)0.0737(16)
H30D0.26560.99531.08120.110*
H30E0.12760.97651.06850.110*
H30F0.18680.93821.11300.110*
O10.1383(2)0.82509(17)1.05705(10)0.0548(8)
O20.0464(2)0.71958(17)1.08627(9)0.0461(8)
O30.1064(3)0.97853(17)0.79499(11)0.0568(9)
O40.0422(3)0.87826(17)0.83700(10)0.0501(8)

Source of material

The powdered whole plants of Pyrrosia lingua were extracted with 90° EtOH under reflux for 3 times, 1 h each time. The combined EtOH extracts were concentrated under vacuum to give a residue, which was suspended in water, then extracted with AcOEt for 3 times. The AcOEt extract was chromatographed on silica gel using gradient elution petroleumether/AcOEt (volume ratio 9:1–1:1) to yield seven fractions (fractions A—E). The title compound (70 mg) was isolated from the fraction B by the silica gel colume chromatography with petroleumether/AcOEt (volume ratio 85:15) and then the sephadex LH-20 with dichloromethane/methanol (volume ratio 1:1). After dissolving the sample with AcOEt colorless needle crystals of the title compound were obtained within 1 day [5].

Experimental details

The crystal structure was solved by direct methods and refined by full-matrix least-squares methods on F2 using SHELXTL-2014 [3]. All hydrogen atoms were positioned geometrically, with the d(C—H) = 0.96–0.98 Å, Uiso(H) = 1.2 times Ueq(C) and Uiso(H) = 1.5 times Ueq(O).

Comment

Pyrrosia lingua is a traditional Chinese herb recorded in Chinese Pharmacopoeia for treating swelling, urocystitis, urinary calculus, bloody urine, cough, bronchitis, etc. and has also been used to cure infection and diarrhoea in minority regions of Guizhou Province. In previous reports, hopane triterpenoids had been isolated from this plant [6]. In order to discover more active hopane triterpenoids from this plant, phytochemical investigation led to the isolation of the title compound. This contribution is part of our continuing interest in natural occurring compounds [7], [8].

The bond lengths and angles derived from the title structure are within normal ranges [8]. The title compound contains one five-membered ring which shows an envelope conformation at C17 and five six-menbered rings which all present chair conformations (cf. the figure). At the same time, the title compound contains an lactone and seven methyl groups, of which C24, C25, C26, C30 are in β-configuration, and C23, C27, C29 are in α-configuration. The lactone was confirmed by the distances d(C22—O1) = 1.477(5), d(C28—O1) = 1.351(5), d(C28—O2) = 1.207(5). The intermolecular connection was achieved by van der Waals forces.

Acknowledgements

The authors gratefully acknowledge support from: Science and Technology Foundation of Guizhou Province [No. J (2013)2071], Youth Science and Technology Talent Project of Guizhou Province [No. (2017)5618], Undergraduate Innovation and Entrepreneurship Project of Guiyang College of Traditional Chinese Medicine [No. (2017)12] and higher-level innovative talent program [No. ZQ2017002].

References

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Received: 2019-03-23
Accepted: 2019-05-06
Published Online: 2019-05-24
Published in Print: 2019-09-25

©2019 Kang He et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

Artikel in diesem Heft

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  41. Crystal structure of diaqua-bis(cinnamato-κ2O,O′)zinc(II), C18H18ZnO6
  42. Crystal structure of 2-(prop-2-yn-1-yloxy)-1-naphthaldehyde, C14H10O2
  43. Crystal structure and photochromic properties of 1-(2-methyl-5-phenyl-3-thienyl)-2-{2-methyl-5-[4-(9-fluorenone hydrazone)-phenyl]-3-thienyl}perfluorocyclopentene, C41H26F6N2S2
  44. Hydrothermal synthesis and crystal structure of cylo[tetraaqua-bis(μ2-1,4-bis(1H-benzo[d]imidazol-1-yl)but-2-ene-κ2N:N′)-bis(μ2-4-nitro-phthalate-κ2O,O′)dinickel(II)], C26H23N5O8Ni
  45. Crystal structure of 3-[methyl(phenyl)amino]-1-phenylthiourea, C14H15N3S
  46. Crystal structure of 1-(4-chlorophenyl)-3-[methyl(phenyl)amino]thiourea, C14H14ClN3S
  47. Crystal structure of 2-tert-butyl-1H-imidazo[4,5-b]pyridine, C10H13N3
  48. Crystal structure of 5-carboxy-2-(2-carboxyphenyl)-1H-imidazol-3-ium-4-carboxylate dihydrate, C12H8N2O6⋅2(H2O)
  49. The crystal structure of dichlorido-μ2-dichlorido-(η2-1,4-bis(4-vinylbenzyl)-1,4-diazabicyclo[2.2.2]octane-1,4-diium)dicopper(I), C24H30N2Cu2Cl4
  50. Crystal structure of 4-bromobenzyl (Z)-N-(adamantan-1-yl)morpholine-4-carbothioimidate, C22H29BrN2OS
  51. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene-1(6bH)-one, C30H48O2
  52. Crystal structure of 3,5-bis(trifluoromethyl)benzyl (Z)-N′-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidate, C30H33F6N3S
  53. The crystal structure of 3-methoxyphenanthridin-6(5H)-one, C14H11NO2
  54. Crystal structure of 4-(5,5-difluoro-1,3,7,9-tetramethyl-3H,5H-5λ4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-10-yl)pyridin-1-ium tetraiodidoferrate(III), C18H19BF2FeI4N3
  55. Crystal structure of 2-(3-methoxyphenyl)-3-((phenylsulfonyl)methyl)imidazo[1,2-a]pyridine, C21H18N2O3S
  56. Crystal structure of [(2-(2-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) perchlorate, C29H50Cl2N4NiO8
  57. Crystal structure of (Z)-6-(dimethylamino)-3,3-bis(4-(dimethylamino)phenyl)-2-(2-(quinoxalin-2-ylmethylene)hydrazinyl)-2,3-dihydroinden-1-one, C35H35N7O
  58. 5-Methyl-N′-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl]-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbohydrazide, C22H22N8O2
  59. Crystal structure of 2,3-dichloro-6-methoxyquinoxaline, C9H6Cl2N2O
  60. Synthesis and crystal structure of 7-chloro-2-(ethylsulfinyl)-6-fluoro-3-(1H-pyrazole-1-yl)-4H-thiochromen-4-one, C13H10FN3OS2
  61. Crystal structure of 4-ethylpiperazine-1-carbothioic dithioperoxyanhydride, C14H26N4S4
  62. Crystal structure of 2-(2-(6-methylpyridin-2-yl)naphthalen-1-yl)pyrimidine, C20H15N3
  63. The crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-3-methylbenzohydrazide, C23H22N2O4
  64. Crystal structure of catena-poly[(μ2-isophthalato-κ2O:O′)-(2,5-di(pyrazin-2-yl)-4,4′-bipyridine-κ3N,N′,N′′)zinc(II)] — water (2/5), C26H21N6O6.5Zn
  65. Crystal structure of (3E,5E)-3,5-bis(3-nitrobenzylidene)-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperidin-4-one — dichloromethane (2/1), C53H38Cl2F6N6O14S2
  66. Crystal structure of (μ2-oxido)-bis(N,N′-o-phenylenebis(salicylideneiminato))diiron(III) — N,N′-dimethylformamide, C47H43Fe2N4O9
  67. Crystal structure of N1,N3-bis(2-hydroxyethyl)-N1, N1,N3,N3-tetramethylpropane-1,3-diaminium dibromide, C11H28Br2N2O2
  68. Crystal structure of (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)methanimine, C12H9ClN2
  69. Crystal structure of 8-bromo-6-oxo-2-phenyl-6H-pyrrolo[3,2,1-ij]quinoline-5-carbaldehyde, C18H11BrNO2
  70. Crystal structure of 1,4-bis(2-azidoethyl)piperazine-1,4-diium dichloride trihydrate, C8H18N8Cl2 ⋅ 3 H2O
  71. Crystal structure of (E)-4-bromo-N-(pyridin-2-ylmethylene)aniline, C12H9BrN2
  72. Crystal structure of bis[(2-(3-bromophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ-O)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Br2N4NiO8
  73. The crystal structure of (1E,2E)-2-methyl-4-((7-oxo-7H-furo[3,2-g]chromen-9-yl)oxy)but-2-enal O-isonicotinoyl oxime–trichloromethane (3/1), C67H49Cl3N6O18
  74. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-methyl-1H-imidazol-3-ium hexafluoridophosphate(V), C8H13F6N2O2P
  75. Crystal structure of bis[(2-(2-bromophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κO)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) hemihydrate C42H65Br2N4NiO8.5
  76. The crystal structure of N-(7-(4-fluorobenzylidene)-3-(4-fluorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbonothioyl)benzamide, C28H23F2N3OS
  77. The crystal structure of N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide, C18H20N4O2
  78. Crystal structure of (E)-2-(3,6-bis(ethylamino)-2,7-dimethyl-9H-xanthen-9-yl)-N′-((6-methylpyridin-2-yl)methylene)benzohydrazide – methanol (1/1), C34H37N5O3
  79. Crystal structure of 2-oxo-1-(pyrimidin-5-ylmethyl)-3-(3-(trifluoromethyl)phenyl)-1,2-dihydro-5l4-pyrido[1,2-a]pyrimidin-4-olate, C20H13F3N4O2
  80. Crystal structure of poly[(μ3-9H-carbazole-3,6-dicarboxylato-κ3O1: O2: O3)(μ2-4-(pyridin-4-yl)pyridine-κ2N1:N1′)zinc(II)], C19H11N2O4Zn
  81. Crystal structure of (E)-N′-((1,8-dihydropyren-1-yl)-methylene)picolinohydrazide, C23H15N3O
  82. Crystal structure of catena-poly{[μ2-1,2-bis(diphenylphosphino)ethane]dichloridocadmium(II)}, C26H24CdCl2P2
  83. Crystal structure of the 1:2 co-crystal between N,N′-bis(4-pyridylmethyl)oxalamide and acetic acid as a dihydrate, C14H14N4O2⋅2 C2H4O2⋅2 H2O
  84. Crystal structure of the co-crystal N,N′-bis(3-pyridylmethyl)oxalamide acetic acid (1/2), C14H14N4O2⋅2C2H4O2
  85. Crystal structure of the co-crystal N,N′-bis(4-pyridylmethyl)oxalamide and 2,3,5,6-tetrafluoro-1,4-di-iodobenzene (1/1), C14H14N4O2⋅C6F4I2
  86. Crystal structure of the co-crystal 4-[(4-carboxyphenyl)disulfanyl]benzoic acid–(1E,4E)-1-N,4-N-bis(pyridin-4-ylmethylidene)cyclohexane-1,4-diamine (1/1), C14H10O4S2⋅C18H20N4
  87. Crystal structure of hexacarbonyl-bis(μ2-di-n-propyldithiocarbamato-κ3S,S′:S3S:S:S′)-di-rhenium(I), C20H28N2O6Re2S4
  88. Crystal structure of fac-tricarbonyl-morpholine-κN-(morpholinocarbamodithioato-κ2S,S′)rhenium(I), C12H17N2O5ReS2
Heruntergeladen am 13.10.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2019-0217/html
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