Home Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H52FNO3
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Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H52FNO3

  • Zi-Yu Liu ORCID logo , Wen-Shui Wang , Sheng Jiang , Feng-Lan Zhao and Qing-Guo Meng EMAIL logo
Published/Copyright: November 2, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 6

Abstract

C36H52FNO3, orthorhombic, P212121 (no. 19), a = 7.8101(5) Å, b = 13.1592(7) Å, c = 30.5721(15) Å, V = 3142.0(3) Å3, Z = 4, R gt(F) = 0.0488, wR ref(F 2) = 0.1048, T = 293 K.

CCDC no.: 2283346

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: 0.14 × 0.13 × 0.10 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: SuperNova
θ max, completeness: 25.5°, >99 %
N(hkl)measured, N(hkl)unique, R int: 14,083, 5656, 0.040
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 4598
N(param)refined: 380
Programs: CrysAlis Pro [1], Shelx [2, 3]
Table 2:

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

Atom x y z U iso*/U eq
C1 0.2736 (4) −0.3268 (2) 0.60107 (10) 0.0250 (7)
C2 0.3357 (4) −0.3750 (2) 0.64263 (10) 0.0273 (7)
C3 0.3896 (4) −0.3084 (2) 0.68110 (9) 0.0248 (7)
C4 0.3414 (4) −0.1948 (2) 0.67523 (9) 0.0248 (7)
H4 0.434761 −0.166349 0.657657 0.030*
C5 0.1788 (4) −0.1746 (2) 0.64796 (9) 0.0230 (7)
C6 0.2154 (4) −0.2176 (2) 0.60193 (9) 0.0268 (7)
H6A 0.112144 −0.211619 0.584477 0.032*
H6B 0.302740 −0.175984 0.588209 0.032*
C7 0.3467 (5) −0.1351 (2) 0.71759 (10) 0.0361 (9)
H7A 0.452246 −0.150402 0.732964 0.043*
H7B 0.251940 −0.155955 0.736044 0.043*
C8 0.3359 (5) −0.0217 (3) 0.70952 (10) 0.0382 (9)
H8A 0.435606 −0.000437 0.692989 0.046*
H8B 0.338266 0.013350 0.737416 0.046*
C9 0.1737 (4) 0.0098 (2) 0.68452 (9) 0.0254 (7)
C10 0.1569 (4) −0.0567 (2) 0.64259 (9) 0.0230 (7)
H10 0.253618 −0.035975 0.624202 0.028*
C11 0.1867 (4) 0.1231 (2) 0.66841 (9) 0.0262 (7)
C12 0.0233 (4) 0.1541 (2) 0.64317 (10) 0.0252 (7)
H12 −0.073750 0.142944 0.662913 0.030*
C13 −0.0052 (5) 0.0868 (3) 0.60347 (11) 0.0388 (9)
H13 0.084795 0.099753 0.581837 0.047*
C14 −0.0025 (5) −0.0254 (2) 0.61640 (12) 0.0357 (9)
H14A −0.008457 −0.066389 0.590070 0.043*
H14B −0.103623 −0.040044 0.633713 0.043*
C15 0.1902 (5) 0.2064 (2) 0.70403 (11) 0.0399 (9)
H15A 0.113487 0.189292 0.727874 0.048*
H15B 0.304927 0.214836 0.715601 0.048*
C16 0.1307 (5) 0.3032 (2) 0.68082 (10) 0.0351 (8)
H16A 0.227824 0.346907 0.674720 0.042*
H16B 0.050710 0.340182 0.699141 0.042*
C17 0.0425 (4) 0.2707 (2) 0.63743 (10) 0.0242 (7)
H17 0.125563 0.281737 0.613869 0.029*
C18 −0.1180 (4) 0.3348 (2) 0.62630 (9) 0.0245 (7)
C19 −0.0723 (5) 0.4475 (2) 0.62659 (11) 0.0324 (8)
H19A −0.063167 0.470455 0.656640 0.039*
H19B 0.038606 0.456517 0.612860 0.039*
C20 −0.2032 (5) 0.5125 (2) 0.60289 (11) 0.0375 (9)
H20A −0.166269 0.582899 0.602909 0.045*
H20B −0.312562 0.508568 0.617834 0.045*
C21 −0.2227 (5) 0.4751 (2) 0.55592 (11) 0.0342 (8)
H21A −0.310335 0.514863 0.541353 0.041*
H21B −0.115732 0.485559 0.540416 0.041*
C22 −0.2707 (4) 0.3631 (2) 0.55375 (10) 0.0271 (8)
C23 −0.2353 (5) 0.3204 (3) 0.50834 (10) 0.0407 (9)
H23A −0.116555 0.329633 0.501283 0.061*
H23B −0.304662 0.355371 0.487232 0.061*
H23C −0.262421 0.249241 0.507876 0.061*
C24 0.0209 (5) −0.0033 (3) 0.71602 (11) 0.0426 (10)
H24A 0.017282 −0.072198 0.726335 0.064*
H24B −0.083650 0.012140 0.700903 0.064*
H24C 0.033974 0.041916 0.740428 0.064*
C25 0.0182 (4) −0.2288 (2) 0.66558 (11) 0.0341 (8)
H25A −0.080099 −0.207812 0.649044 0.051*
H25B 0.002056 −0.211505 0.695803 0.051*
H25C 0.032559 −0.301023 0.662878 0.051*
C26 0.3226 (5) −0.3560 (3) 0.72356 (10) 0.0385 (9)
H26A 0.200502 −0.348153 0.724964 0.058*
H26B 0.374240 −0.322590 0.748169 0.058*
H26C 0.351060 −0.426917 0.724130 0.058*
C27 −0.4583 (5) 0.3454 (3) 0.56552 (11) 0.0378 (9)
H27A −0.479512 0.273782 0.567913 0.057*
H27B −0.530075 0.373634 0.543107 0.057*
H27C −0.483262 0.377737 0.592940 0.057*
C28 0.3478 (4) 0.1416 (2) 0.64014 (12) 0.0391 (9)
H28A 0.357358 0.212725 0.633615 0.059*
H28B 0.338415 0.103850 0.613372 0.059*
H28C 0.447548 0.119693 0.655865 0.059*
C29 0.5871 (4) −0.3165 (3) 0.68134 (10) 0.0302 (8)
H29A 0.620064 −0.385251 0.687705 0.045*
H29B 0.633022 −0.272005 0.703276 0.045*
H29C 0.630984 −0.297406 0.653180 0.045*
C30 0.2775 (4) −0.3863 (2) 0.56560 (10) 0.0289 (8)
H30 0.316251 −0.452238 0.570331 0.035*
C31 0.2294 (4) −0.3627 (2) 0.52022 (10) 0.0271 (8)
C32 0.1819 (4) −0.4402 (2) 0.49228 (10) 0.0277 (7)
C33 0.1323 (4) −0.4243 (3) 0.44958 (10) 0.0318 (8)
H33 0.099547 −0.479751 0.432689 0.038*
C34 0.1780 (6) −0.2557 (3) 0.45767 (11) 0.0436 (10)
H34 0.178044 −0.190536 0.445946 0.052*
C35 0.2278 (5) −0.2669 (3) 0.50075 (11) 0.0393 (9)
H35 0.260412 −0.210137 0.516866 0.047*
C36 −0.2667 (5) 0.3112 (3) 0.65699 (10) 0.0362 (9)
H36A −0.351862 0.363485 0.654524 0.054*
H36B −0.225632 0.308380 0.686570 0.054*
H36C −0.316076 0.246914 0.649212 0.054*
F1 0.1806 (3) −0.53701 (13) 0.50769 (6) 0.0389 (5)
N1 0.1299 (4) −0.3320 (2) 0.43173 (9) 0.0384 (7)
O1 −0.1569 (3) 0.30433 (14) 0.58156 (6) 0.0254 (5)
O2 −0.1682 (5) 0.10256 (19) 0.58389 (12) 0.0840 (12)
H2 −0.183301 0.163538 0.579934 0.126*
O3 0.3489 (3) −0.46721 (16) 0.64538 (7) 0.0382 (6)

1 Source of material

Total saponins of ginseng stem and leaves were degraded by 18 % sulfuric acid in ethanol and refluxed for 4 h. Cooled to room temperature, the reaction solution was adjusted to neutral with appropriate amount of sodium carbonate, the residue was extracted with ethyl acetate, dried with anhydrous sodium sulfate, filtered, and concentrated under pressure to obtain the crude product, and the crude product was recrystallized with ethyl acetate to obtain the pure product of 20(R)-panaxadiol. 20(R)–Panaxadiol and PCC were dissolved in 25 mL of dichloromethane solution and purified by silica gel column chromatography after stirring at room temperature for 5 h to obtain 20(R)-3-oxopanaxadiol. 20(R)-3-Oxopanaxadiol (100 mg, 0.22 mmol) and 3-fluoropyridine-4-carboxaldehyde (0.02 mL, 0.22 mmol) were dissolved in 1.4 mL of methanol, 0.72 mL of 25 % aqueous sodium hydroxide solution was added and stirred at room temperature for 5 h. The response endpoint was detected by thin layer chromatography (TLC). At the end of the reaction, it was extracted with ethyl acetate and washed with brine. The product was concentrated under reduced pressure and purified by silica gel column chromatography. The single crystal of the title compound was obtained by recrystallization with ethyl acetate solution.

2 Experimental details

The H atoms were placed in idealized positions and treated as riding on their parent atoms, with d (C–H) = 0.96 Å (methyl), U iso(H) = 1.5U eq(C), and d(C–H) = 0.97 Å (methylene), U iso(H) = 1.2U eq(C), and d(C–H) = 0.98 Å (methyne), U iso(H) = 1.2U eq(C), and d(C–H) = 0.93 Å (aromatic), U iso(H) = 1.2U eq(C). H atoms on hydroxyl group were located in different maps and treated as riding.

3 Comment

Ginsenosides are divided into protopanoxadiol-type sapogenin, protopanoxatriol-type sapogenin and oleanolic acid type sapogenin [4]. The configuration of C20 of 20(S)-protopanoxadiol-type sapogenin is easily converted to R type when treated with an inorganic acid [5]. The synthesis and single crystal X-ray diffraction of 20(S)-propanaxanediol, 20(R)-propanaxanediol, 20(R)-panaxadiol and their derivatives have been studied in our group [6], [7], [8], [9], [10]. The title compound is the 20(R)-panaxadiol derivative.

The title compound has a dammarane type as the parent structure [11], with a pyridine ring structure attached to C(1). An α,β-unsaturated ketone group is formed between the pyridine group and the parent nucleus by the Claisen–Schmidt reaction effect. The angle of twist of C(30)=C(1)–C(2)=O(3) is −16.5(5)°. The bond length of C(30)=C(1) is 1.338(4) Å. The bond length of C(2)=O(3) is 1.221(4) Å. Formation of a Z-configuration between the pyridine ring and the carbonyl group [12]. In addition, the pyridinyl group is substituted with a fluorine atom and the C–F bond length is 1.359(3) Å. The presence of α,β-unsaturated ketone groups and fluorine atoms in the molecule facilitates the enhancement of the biological activity of the molecule [13]. The first ring contains a carbon-oxygen double bond and the bond length of C(2)–O(3) is 1.221(4) Å. The bond length of C(13)–O(2) is 1.422(4) Å. Bond length of C(22)–O(1), C(18)–O(1) in the tetrahydropyran ring are 1.455(3), 1.458(3) Å respectively. The molecules C(5), C(8), C(9), C(10), C(12), C(13), C(14), and C(17) are all chiral carbons, all of which are in the R conformation except C(17), which is in the S conformation. There is a pyran ring substitution at the C17 position, and the oxygen atom on the ring acts as a hydrogen bond acceptor to form an intramolecular O–H⋯O hydrogen bond. In the crystal structure, the pyridine ring has a planar conformation, and all the six-membered rings, except the ketone-containing ring, have a chair conformation with bond lengths and angles within the expected range.

Corresponding author: Qing-Guo Meng, School of Pharmacy, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Yantai University, Yantai, P.R. China, E-mail:

Funding source: Science and Technology Innovation Development Plan of Yantai

Award Identifier / Grant number: 2020XDRH105

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 81473104

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

  2. Research funding: This work was supported by Science and Technology Innovation Development Plan of Yantai (No. 2020XDRH105) and the National Natural Science Foundation of China (No. 81473104).

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

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Received: 2023-09-29
Accepted: 2023-10-26
Published Online: 2023-11-02
Published in Print: 2023-12-15

© 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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  30. The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
  31. Crystal structure of 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one, C10H10O2
  32. Crystal structure of bis(tetrapropylammonium) dodecacarbonyltetratelluridotetraferrate(2-), (Pr4N)2[Fe4Te4(CO)12]
  33. The crystal structure of poly[bis(μ2−3−aminopyridine−4−carboxylato−κ2N:O)Zinc(II)], [Zn(C6H5N2O2)2] n
  34. The crystal structure of methyl 5-nitro-2-(tosyloxy)benzoate, C15H13NO7S
  35. The crystal structure of 18-crown-6 ― tetraaqua-dichlorido-di-μ2-chloridodicopper(II) (2/1), C12H32O10Cu2Cl4
  36. Crystal structure of 6,6a,7,8,9,10-hexahydro-5H-pyrazino [2,3-e]pyrido[1,2-a]pyrazine, C10H14N4
  37. Crystal structure of catena-poly-{diaqua-bis[μ-(((4-chlorophenyl)sulfonyl)glycinato-κO)](μ2-4, 4′-bipyridine-κ2N:N′)cobalt(II)} dihydrate, C26H30Cl2CoN4O12S2
  38. Crystal structure of bis{N′-[1,3-diphenylprop-2-en-1-ylidene]-N-phenylcarbamohydrazonothioato}zinc(II), C44H36N6S2Zn
  39. Crystal structure of tetraaqua-bis(((4-chlorophenyl)sulfonyl)glycinato-κO)cobalt(II) dihydrate, C16H26Cl2CoN2O14S2
  40. Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
  41. Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
  42. Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  43. Crystal structure of (2-phenylimino methylquinoline-κ 2 N,N′)-bis(1–phenylpyrazole-κ 2 C,N)-iridium(III) hexafluorophosphate, C34H26F6IrN6P
  44. Crystal structure of (3-hydroxy-4-methoxyphenyl)(pyrrolidin-1-yl)methanone, C12H15NO3
  45. The crystal structure of bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)] C6H18O2S2NaInBr6
  46. Crystal structure of N-cyclopropyl-3-hydroxy-4-methoxybenzamide, C11H13NO3
  47. The crystal structure of (bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″ )-(dihydrogen L-malate-κ2O,O ′)copper(II) perchlorate dihydrate, CuC20H24ClN5O12
  48. Crystal structure of (1E,1′E)-4,4′-(9,9-diethyl-9H-fluorene-2,7-diyl)dibenzaldehyde dioxime, C31H28N2O2
  49. Crystal structure of diethyl 1,9-bis(4-fluorophenyl)-4,6-diphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta [b]pyridine-3,7(2H)-dicarboxylate, C40H36F2N2O4
  50. Crystal structure of bis(benzene-1 carboxylato-O 3,5-carboxyl-κ1O)-[(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) ─ benzene-1,3,5-tricarboxylic acid ─ water (1/2/4), C52H66N4NiO28
  51. Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
  52. Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
  53. Crystal structure of 1,4-dibromo-2,5-bis(prop-2-yn-1-yloxy)benzene, C12H8Br2O2
  54. Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl carbonothioate, C24H15NO2S2
  55. The crystal structure of (E)-4-fluoro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
  56. Crystal structure of (E)-1-(benzo[d]thiazol-2-yl)-N-(4,5-dihydropyren-2-yl)methanimine, C24H16N2S
  57. Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
  58. Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H52FNO3
https://doi.org/10.1515/ncrs-2023-0429
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of bis(dimethylammonium) poly[(μ4-1,1′-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato))-κ6O1, N2:O2:O3:O1′,N2′]nickel (II)], C22H26N6NiO8
  4. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-((pyridin-4-ylmethyl)amino)benzoato-κ2N:O)cobalt(II)] – 4,4′-bipyridine – water (1/2/2)
  5. Crystal structure of (2S,3S,4S,5S, Z)-2,3,5,6-tetrakis(benzyloxy)-4-hydroxyhexanal oxime, C34H37NO6
  6. The crystal structure of hexakis(3-thiophenecarboxylato-κ2O,O″)-bis(1,10-phenanthroline-κ2N,N′) trimanganese(II), C54H34N4O12S6Mn3
  7. Crystal structure of catena-poly[(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(4-bromobenzoate-κ2O:O′)-(μ-2-bromobenzoate-κ2O,O′)nickel(II)] – water (2/1), C30H21Br2N2NiO4.5
  8. The crystal structure of poly[(μ3-1,3-phenylenedioxydiacetate-κ5O,O,O′,O″,O‴)-bis(4′-(4-(1H-imidazol-1-yl)phenyl)-4,2′:6′,4″-terpyridine-kN) cadmium(II)], C58H42CdN10O6
  9. The crystal structure of 5-chloro-6′-methyl-3-(4-(methylsulfonyl)phenyl)-[2,3′-bipyridin]-1′-ium 4-methylbenzenesulfonate
  10. Crystal structure of poly[(μ-benzoato)-(μ-cis-4–hydroxy-D-proline)lithium], C12H14LiNO5
  11. The crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O′)-copper(II)] monohydrate, C7H6NO6ICu
  12. The crystal structure of catena-[diaqua-(4-acetylphenoxyacetato-κ2O,O)-bis(4-acetylphenoxyacetato-κ3O,O:O)-dihydrate-lanthanum(III)]–4,4′-bipyridine (2/1), C35H35NO14La
  13. The crystal structure of catena-poly[(4-iodopyridine-2,6-dicarboxylato-κ4 O,N,O′,O′′)(4-imidazol-1-yl-pyridine-κN)copper(II)], C15H9N4O4ICu
  14. Crystal structure of polybis(μ 4-3,5-dicarboxylatopyrazol-1-yl)-bis(N,N-dimethylformamide)tri-copper(II)–acetonitrile (1/2), C20H22Cu3N8O10
  15. Crystal structure of poly[(μ2-5-hydroxy-isophthalato-κ4O,O′:O″,O‴)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)cadmium(II)], C21H24CdN4O5
  16. The crystal structure of poly[bis(μ2-1,4-bi(1-imidazolyl)benzene-κ2N:N′)bis(μ2-4,4′-methylenebis(3-hydroxy-2-naphthoate)-κ2O:O′)cobalt(II)], C35H24CoN4O6
  17. The crystal structure of a cobalt-vanadium-oxido hydrate
  18. The crystal structure of catena-poly[(μ 2-2H-1,2,3-triazole-4,5-dicarboxylato-κ 2 O, O′)-(μ 2-1,3-bis((1H-imidazol-1-yl)methyl)benzene-κ 2 N,N′) zinc(II)], C18H15N7O4Zn
  19. Crystal structure of poly[diaqua-(bis(m2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′-manganese] dichloride, C28H32MnN8O2Cl2
  20. The crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino [3,2-a]isoquinolin-7-ium (E)-3-(4-nitrophenyl)acrylate pentahydrate, C29H34N2O13
  21. Crystal structure of poly[(μ6-ammoniotris(methylene))tris(hydrogen phosphonato)cadmium(II)], C3H10CdNO9P3
  22. Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2
  23. The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2
  24. Crystal structure of (E)-2-(2-(4-(diethylamino)styryl)-1-ethyl-1,4-dihydroquinolin-4-yl) malononitrile, C26H26N4
  25. Crystal structure of ethyl 2-((2,6-dichloro-4-(cyanomethyl)phenyl) amino)benzoate, C17H14Cl2N2O2
  26. Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3
  27. The crystal structure of bis(acetonitrile-κ1N)tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)rhodium(II) (Rh–Rh), C32H18F8O8N2Rh2
  28. The crystal structure of a new polymorph of 6-hydroxy-2-naphthoic acid, C11H8O3
  29. The crystal structure of [(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)-2,2′-bipyridine-κ2N-copper(II)] tetrahydrate, C22H23N3O9Cu
  30. The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
  31. Crystal structure of 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one, C10H10O2
  32. Crystal structure of bis(tetrapropylammonium) dodecacarbonyltetratelluridotetraferrate(2-), (Pr4N)2[Fe4Te4(CO)12]
  33. The crystal structure of poly[bis(μ2−3−aminopyridine−4−carboxylato−κ2N:O)Zinc(II)], [Zn(C6H5N2O2)2] n
  34. The crystal structure of methyl 5-nitro-2-(tosyloxy)benzoate, C15H13NO7S
  35. The crystal structure of 18-crown-6 ― tetraaqua-dichlorido-di-μ2-chloridodicopper(II) (2/1), C12H32O10Cu2Cl4
  36. Crystal structure of 6,6a,7,8,9,10-hexahydro-5H-pyrazino [2,3-e]pyrido[1,2-a]pyrazine, C10H14N4
  37. Crystal structure of catena-poly-{diaqua-bis[μ-(((4-chlorophenyl)sulfonyl)glycinato-κO)](μ2-4, 4′-bipyridine-κ2N:N′)cobalt(II)} dihydrate, C26H30Cl2CoN4O12S2
  38. Crystal structure of bis{N′-[1,3-diphenylprop-2-en-1-ylidene]-N-phenylcarbamohydrazonothioato}zinc(II), C44H36N6S2Zn
  39. Crystal structure of tetraaqua-bis(((4-chlorophenyl)sulfonyl)glycinato-κO)cobalt(II) dihydrate, C16H26Cl2CoN2O14S2
  40. Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
  41. Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
  42. Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  43. Crystal structure of (2-phenylimino methylquinoline-κ 2 N,N′)-bis(1–phenylpyrazole-κ 2 C,N)-iridium(III) hexafluorophosphate, C34H26F6IrN6P
  44. Crystal structure of (3-hydroxy-4-methoxyphenyl)(pyrrolidin-1-yl)methanone, C12H15NO3
  45. The crystal structure of bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)] C6H18O2S2NaInBr6
  46. Crystal structure of N-cyclopropyl-3-hydroxy-4-methoxybenzamide, C11H13NO3
  47. The crystal structure of (bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″ )-(dihydrogen L-malate-κ2O,O ′)copper(II) perchlorate dihydrate, CuC20H24ClN5O12
  48. Crystal structure of (1E,1′E)-4,4′-(9,9-diethyl-9H-fluorene-2,7-diyl)dibenzaldehyde dioxime, C31H28N2O2
  49. Crystal structure of diethyl 1,9-bis(4-fluorophenyl)-4,6-diphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta [b]pyridine-3,7(2H)-dicarboxylate, C40H36F2N2O4
  50. Crystal structure of bis(benzene-1 carboxylato-O 3,5-carboxyl-κ1O)-[(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) ─ benzene-1,3,5-tricarboxylic acid ─ water (1/2/4), C52H66N4NiO28
  51. Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
  52. Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
  53. Crystal structure of 1,4-dibromo-2,5-bis(prop-2-yn-1-yloxy)benzene, C12H8Br2O2
  54. Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl carbonothioate, C24H15NO2S2
  55. The crystal structure of (E)-4-fluoro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
  56. Crystal structure of (E)-1-(benzo[d]thiazol-2-yl)-N-(4,5-dihydropyren-2-yl)methanimine, C24H16N2S
  57. Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
  58. Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H52FNO3
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