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Crystal structure of camptothecin, C20H16N2O4

  • Zhuo-Jie Tan , Yun-Bo Wang , Quan-Nu Yang , Yao-Lan Li , Guo-Cai Wang , Yong-Zhong Ouyang and Guo-Qiang Li EMAIL logo
Published/Copyright: February 16, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 233 Issue 3

Abstract

C20H16N2O4, monoclinic, P21 (no. 4), a = 8.0094(5) Å, b = 6.7689(3) Å, c = 29.577(2) Å, β = 95.809(6)°, V =1595.27(16) Å3, Z = 4, Rgt(F) = 0.0457, wRref(F2) = 0.1209, T = 293 K.

CCDC no.: 1558968

The asymmetric unit of the title crystal structure (systematic name: (S-)4-Ethyl-4-hydroxy-1H-pyrano[3′,4′:6,7]indolizino[1,2-b]chinolin-3,14-(4H,12H)-dion) 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:Needle, clear light yellow
Size:0.3 × 0.22 × 0.1 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:0.85 mm−1
Diffractometer, scan mode:Gemini S Ultra, ω-scans
θmax, completeness:63.3°, >98%
N(hkl)measured, N(hkl)unique, Rint:10754, 4004, 0.053
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3089
N(param)refined:473
Programs:CrysAlisPRO [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
N1−0.0325(5)0.4660(6)0.23580(13)0.0461(10)
N1′0.3623(5)0.5509(6)0.74856(12)0.0441(9)
N40.2024(5)0.0847(5)0.29496(13)0.0440(9)
N4′0.5932(5)0.9503(5)0.80164(12)0.0424(9)
O10.5247(5)0.2263(6)0.43384(12)0.0660(10)
O1′0.7023(5)0.9753(5)0.96206(10)0.0530(9)
O20.5591(6)0.5453(7)0.44316(19)0.0998(16)
O2′0.5583(5)0.7590(5)0.99745(12)0.0640(10)
O30.2495(5)0.6425(5)0.40474(12)0.0637(10)
H30.30710.68340.38540.096*
O3′0.5380(4)0.4948(5)0.92857(10)0.0491(8)
H3′0.53040.46250.95500.074*
O40.3506(5)−0.1684(5)0.32979(12)0.0588(9)
O4′0.7326(5)1.2176(5)0.83315(11)0.0546(9)
C20.0467(6)0.3025(7)0.24926(16)0.0452(11)
C2′0.4406(6)0.7161(7)0.75967(15)0.0413(10)
C30.1358(6)0.2713(6)0.29446(15)0.0412(11)
C3′0.5281(6)0.7618(6)0.80417(14)0.0378(10)
C50.1631(7)−0.0208(7)0.25146(15)0.0486(12)
H5A0.0984−0.13950.25550.058*
H5B0.2646−0.05570.23800.058*
C5′0.5510(6)1.0440(7)0.75692(15)0.0458(11)
H5′A0.65111.07640.74260.055*
H5′B0.48471.16260.75940.055*
C60.0619(6)0.1291(7)0.22312(16)0.0456(11)
C6′0.4504(6)0.8836(7)0.73125(16)0.0452(11)
C7−0.0086(6)0.1272(7)0.17966(16)0.0492(12)
H70.00180.01760.16120.059*
C7′0.3750(7)0.8776(7)0.68805(16)0.0506(12)
H7′0.38150.98360.66830.061*
C8−0.0996(6)0.2981(8)0.16277(17)0.0496(12)
C8′0.2856(6)0.7025(8)0.67425(15)0.0461(11)
C9−0.1794(6)0.3104(9)0.11811(17)0.0572(14)
H9−0.17700.20280.09860.069*
C9′0.2005(7)0.6808(9)0.63060(17)0.0578(14)
H9′0.19960.78480.61000.069*
C10−0.2603(7)0.4798(10)0.10330(18)0.0623(15)
H10−0.31260.48620.07380.075*
C10′0.1200(7)0.5110(10)0.61814(18)0.0665(16)
H10′0.06320.50000.58920.080*
C11−0.2655(7)0.6420(9)0.13166(18)0.0635(15)
H11−0.31870.75710.12070.076*
C11′0.1213(7)0.3530(9)0.64804(17)0.0596(14)
H11′0.06840.23560.63860.072*
C12′0.1988(7)0.3676(8)0.69093(16)0.0530(13)
H12′0.19540.26210.71100.064*
C12−0.1939(7)0.6353(8)0.17519(17)0.0544(13)
H12−0.20290.74350.19420.065*
C13−0.1049(6)0.4640(7)0.19204(16)0.0476(11)
C13′0.2848(6)0.5429(7)0.70522(15)0.0429(11)
C140.1587(6)0.3917(7)0.33114(15)0.0457(11)
H140.11370.51840.33040.055*
C14′0.5490(6)0.6563(6)0.84340(13)0.0376(10)
H14′0.51050.52700.84470.045*
C150.2527(6)0.3187(7)0.37031(16)0.0461(12)
C15′0.6307(5)0.7495(6)0.88193(14)0.0375(10)
C160.3204(6)0.1326(7)0.37061(16)0.0473(12)
C16′0.6924(6)0.9371(6)0.87931(15)0.0402(11)
C170.4281(7)0.0652(7)0.41236(19)0.0593(14)
H17A0.35730.00910.43380.071*
H17B0.5039−0.03730.40400.071*
C17′0.7678(7)1.0402(7)0.92075(16)0.0524(12)
H17C0.88821.01920.92370.063*
H17D0.74801.18100.91710.063*
C180.1983(13)0.4798(17)0.4934(2)0.128(4)
H18A0.18870.62000.48890.192*
H18B0.30910.44860.50700.192*
H18C0.11710.43690.51300.192*
C18′0.8763(7)0.4715(8)0.98215(16)0.0590(14)
H18D0.98470.41010.98350.088*
H18E0.79300.37350.98670.088*
H18F0.87670.57041.00540.088*
C190.1671(8)0.3769(10)0.44853(17)0.0672(16)
H19A0.05160.40010.43650.081*
H19B0.18060.23590.45350.081*
C19′0.8359(6)0.5671(7)0.93602(16)0.0465(11)
H19C0.85360.47090.91270.056*
H19D0.91350.67530.93310.056*
C200.2829(7)0.4418(7)0.41269(16)0.0510(13)
C20′0.6552(6)0.6468(6)0.92751(14)0.0393(10)
C210.4662(7)0.4127(8)0.43145(19)0.0621(15)
C21′0.6320(6)0.7988(7)0.96485(16)0.0467(11)
C220.2960(6)0.0031(7)0.33232(16)0.0455(11)
C22′0.6776(6)1.0495(7)0.83776(16)0.0438(11)

Source of material

The dry fruit of Camptotheca acuminata was purchased from Guangzhou qingping medicine market, Guangdong, China. The powdered fruit of C. acuminata (25 kg) was extracted three times with 95% ethanol at room temperature. The solution was concentrated in vacuum to get a residue (2.8 kg), which was suspended in water and partitioned with petroleum ether and then ethyl acetate to yield the ethyl acetate extract (432 g). The ethyl acetate extract was subjected to a silica gel column chromatography (12 × 120 cm, 4000 g) using the petroleumether-ethyl acetate solvent system (100:0, 95:5, 90:10, 80:20, 70:30, 60:40, 50:50, 0:100) to afford eight fractions (Fr. A-H). Fraction E (30.50 g) was further subjected to a silica gel column chromatography (6 × 60 cm, 500 g) eluted with CHCl3—CH3OH (100:0, 90:10, 80:20, 70:30, 50:50, 0:100), which provided six subfractions (Fr.E1—E6). Subfraction Fr.E4 (400 mg) was purified by Sephadex LH-20 column chromatography (CH3OH) and the title compound was crystallized from the eluent.

Experimental details

The C-bound H atoms were positioned geometrically and were included in the refinement in the riding-model approximation. The crystal structure was solved by direct method and refined by full-matrix least-squares refinement with SHELX program [2]. The Flack paramter was found to be 0.1(3) based on 740 quotients [2].

Discussion

Camptotheca acuminata (Chinese happy tree), a tree native to mainland China, belongs to the Nyssaceae family [3], [4]. The dried ripe fruit of C. acuminata has long been used in traditional Chinese medicine for the treatment of cancer [5], and the title compound, camptothecin (CPT), is the main active constituent [6]. It is a quinoline alkaloid originally isolated from C. acuminata [7] and well-known as a topoisomerase inhibitor possessing a proven anti-cancer activity against various cancer cell lines [8, 9] . The phase of clinical trials of CPT have been completed, and it is now used as a chemotherapeutic reagent [4]. Moreover, some modern studies revealed that CPT also has insecticidal activity [10], and the derivatives of CPT were designed, synthesized as well due to its biological activities [11], such as the 5-aryl-(20S)-camptothecin derivatives [12]. In addition, the crystal of camptothecin iodoacetate was obtained and its crystal structure was analysed, which has defined the constitution and absolute stereochemistry of CPT [13]. However, there was still no report on the crystal structure of CPT.

There are two crystallographically independent molecules in the asymmetric unit (cf. the figure). Both molecules are almost identical concerning their geometric parameters. To keep it simple, only one molecule is described in detail. The title compound is composed of five rings, one quinoline moiety, one indolizino moiety and a pyrano ring. The carbon atoms C(8), C(9), C(10), C(11), C(12), C(13) are coplanar constructing the phenyl ring (plane 1, mean deviation 0.009 Å) and the atoms N(1), C(2), C(6), C(7), C(8), C(13) are also coplanar (plane 2, mean deviation 0.008 Å). Plane 1 and plane 2 of which dihedral angle is 0.6° form the quinoline moiety by fusing the atoms of C(8) and C(13). The indolizino moiety consists of plane 3 [atoms: N(4), C(5), C(6), C(2), C(3), mean deviation 0.002 Å] and plane 4 [atoms: N(4), C(3), C(14), C(15), C(16), C(22), mean deviation 0.005 Å] in which the dihedral angle is 0.4°. The atoms C(15), C(16), C(17), O(1), C(21), C(20) form the pyrano ring adopting a Boat conformation with the puckering parameters [14] Q = 0.5492(2) Å, θ = 83.08°, φ = 245.0776°.

Acknowledgements

This work was supported financially by grants from the national Natural Science Foundation of China (no. 21405013), the Fundamental Research Funds for the Central Universities (Grant gg040971), the Natural Science Foundation of Guangdong Province (Grant 2016A030310079).

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Received: 2017-10-7
Accepted: 2018-1-30
Published Online: 2018-2-16
Published in Print: 2018-5-24

©2018 Zhuo-Jie Tan 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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  42. Crystal Structure of bis(1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O)copper(II), C24H22N8O4S2Cu
  43. Synthesis and crystal structure of poly[aqua{μ3-(1S,2S)-1-((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)pyrrolidin-1-ium-2-carboxylato-κ4O,O′:O′′:O′′′}sodium(I)] monohydrate, C21H22NNaO11S
  44. Halogen bonds in the crystal structure of 1,4-diiodotetrafluorobenzene–1,2-bis(4-pyridyl)propane (1/1), C19H14F4I2N2
  45. Crystal structure of bis(μ-N-i-propyl-N-n-propyldithiocarbamato-κ2S:S′) bis(N-i-propyl-N-n-propyldithiocarbamato-κ2S,S′)dizinc(II), C28H56N4S8Zn2
  46. Crystal structure of bis(μ-N-i-propyl-N-n-propyldithiocarbamato-κ3S,S′:S)bis(N-i-propyl-N-n-propyldithiocarbamato-κ2S,S′)dicadmium(II), C28H56Cd2N4S8
  47. Crystal structure of bis(μ2-di-n-butyldithiocarbamato-κ3S,S′:S;κ3S:S:S′)-hexacarbonyl-di-rhenium(I), C24H36N2O6Re2
  48. Crystal structure of 7-(4-methylphenyl)imidazo[1,2-a][1,3,5]triazin-4-amine, C12H11N5
  49. Crystal structure of the co-crystal O-isopropyl phenylcarbamothioate – 4,4′-bipyridine (2/1), C15H17N2OS
  50. Crystal structure of the coordination polymer catena-poly[chlorido-{μ2-2-(((3,5-dimethyl-1H-pyrazol-1-yl)methyl)amino)-3-hydroxybutanoato-κ4N,N,O:O′}copper(II)], C11H16ClCuN2O3
  51. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-di(ethanol)-bis{μ2-5-(N,N′-diethylamine)-5′-methoxyl-2,2′-[ethylenediyldioxybis(nitrilomethylidyne)]diphenolato-κ6O:O,N,N,O′:O′}trinickel(II) – ethanol – acetonitrile (1/2/2), C58H86Ni3N8O18
  52. Crystal structure of the bis((E)-O-ethyl-N-phenylthiocarbamate) – 4,4′-bipyridine co-crystal (2/1), C28H30N4O2S2
  53. Crystal structure of the (E)-O-methyl-N-phenyl-thiocarbamate – 4,4′-bipyridine (1/1), C18H17N3OS
  54. Crystal structure of bis(μ2-diethyldithiocarbamato-κ3S,S′:S′)-bis(tricyclohexylphosphane-κP)dicopper(I), C46H86Cu2N2P2S4
  55. Crystal structure of N-(3-chlorophenyl)ethoxycarbothioamide, C9H10ClNOS
  56. Crystal structure of bis(μ2-pyrrolidine-1-carbodithioato-κ3S,S′:S;κ3S:S:S′)-bis(tricyclohexylphosphane-P)-di-copper(I), C46H82Cu2N2P2S4
  57. Crystal structure of N-(2-chlorophenyl)methoxycarbothioamide, C8H8ClNOS
  58. Crystal structure of chlorido-methanol-(N-(2-(oxy)-3-methoxybenzylidene)pyridine-4-carbohydrazonato-κ3O,N,O′)-(4-methylphenyl)methyl-tin(IV), C23H24ClN3O4Sn
  59. Crystal structure of N-(3-chlorophenyl)(propan-2-yloxy)carbothioamide, C10H12ClNOS
  60. Crystal structure of 1-[(Z)-[4-(4-methoxyphenyl)butan-2-ylidene]amino]-3-phenylurea, C18H21N3O2
  61. A triclinic polymorph of bis(μ-N,N-bis(2-hydroxyethyl)dithiocarbamato-κ3S,S′:S′) bis(N,N-bis(2-hydroxyethyl)dithiocarbamato-κ2S:S′)zinc(II), C20H40N4O8S8Zn2
https://doi.org/10.1515/ncrs-2017-0244
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Bis(tetraethylammonium) carbonate – boric acid – water (1/2/5), C17H56B2N2O14
  3. Crystal structure of 4-methoxy-6-phenyl-2H-pyran-2-one, C12H10O3
  4. Crystal structure of tris{(3-((E)-(((E)-2-oxidobenzylidene)hydrazono)methyl)-2-oxo-2H-chromen-4-olato-κ3O,N:N′)}dicobalt(III)tris(dimethylformamide), C60H50Co2N9O15
  5. Crystal structure of poly[bis(1-methyl-[4,4′-bipyridin]-1-ium-κN)-tetrakis(μ3-sulfato-κ3O:O′:O′′)trizinc(II)], C22H22Zn3N4O16S4
  6. Crystal structure of (5Z,10Z)-3,13-dichloro-17,18-dioxo-5,11-diphenyl-8,9,17,18-tetrahydro-7H-dibenzo[e,n][1,4,8,12]tetraazacyclopentadecine-16,19-diido-κ4N,N′,N′′,N′′′)copper(II), C31H22N4O2Cl2Cu
  7. Crystal structure of bis{5-methoxy-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2N,O}zinc(II), C34H24N2O8Zn
  8. Crystal structure of 2,2′-((((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))diphenolato-κ2N;κ4O)nickel(II), C28H22N2O4Ni
  9. Crystal structure of 1,1′-((1E,1′E)-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(naphthalen-2-olato)cobalt(II), C36H26N2O4Co
  10. Crystal structure of camptothecin, C20H16N2O4
  11. Crystal structure of (2-(chlorophenyl)-5-methyl-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 monohydrate, Ni(C16H36N4)(C12H12O4Cl)ClO4⋅H2O
  12. Crystal structure of 3-(2-chloro-6-methoxyquinolin-3-yl)-5-phenylisoxazole (C19H13ClN2O2)
  13. Crystal structure of tetrakis(μ2-acetato-κ2O:O′)-bis{[(E)-2,6-diisopropyl-N-(pyridin-3-ylmethylene)aniline]copper (II)}, C44H56Cu2N4O8
  14. Crystal structure of diethyl 2-(2-chlorophenyl)-1,3-dioxane-5,5-dicarboxylate, C16H19Cl1O6
  15. Crystal structure of (μ2-2,2′-bipyridine-3,3′-dicarboxylato)-bis(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane)-di-nickel(II) perchlorate N,N′-dimethylformamide solvate, C50H92Cl2N12Ni2O14
  16. Crystal structure of catena-poly[triaqua(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′)-(1,2-bis(4-pyridyl)ethane-κN)nickel(II)] 2-aminonicotinate nitrate – 1,2-bis(4-pyridyl)ethane – water (2/1/8), C36H44N8NiO12
  17. Hydrothermal synthesis and crystal structure of poly[bis(μ2-3-(3,5-dicarboxyphenoxy)phthalato-κ3O,O′:O′′)-(μ2-1,2-di(pyridin-4-yl)ethane-κ2N:N′)copper(II)], C22H14CuNO9
  18. Crystal structure of catena-poly[aqua-(methanol-κO)-bis(μ2-4-(pyridin-4-yl)benzoato-κ2N:O)-bis(triphenylphospine-κP)disilver(I)], C61H52Ag2N2O6P2
  19. The crystal structure of 6-(4-bromobenzyl)-1,3,5-trimethyl-7-phenyl-1,5-dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-dione, C22H20BrN3O2
  20. Synthesis and crystal structure of catena-poly[bis(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetato-κO;κ2O′,O′′)-(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)zinc(II)], C44H32N4ZnCl4O4
  21. Crystal structure of diaqua-bis[N-phenyl-2-(quinolin-8-yloxy)acetamide-κ3-N,O,O′]-nitrato(κ2O,O′)-cerium(III) dinitrate - acetone (1/2), C40H44N7O17Ce
  22. Crystal structure of the 2D coordination polymer poly[aqua(μ2-2,2′-(1,2-phenylene)diacetato-κ3O,O′:O′)-(μ2-4,4′-bis((1H-1,2,4-triazol-1-yl)methyl)-1,1′-biphenyl-κ2N:N′)cobalt(II)], C28H26CoN6O5
  23. Crystal structure of (dimethylformamide-κO)(perchlorato-κ2O,O′){μ2-6,6′-((1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(4-bromo-2-methoxyphenolate)-κ8N,N′,O:O,O′:O′,O′′,O′′′}sodium(I)nickel(II), C25H23Br2ClN3NaNiO9
  24. The crystal structure of catena-poly[bis((4-aminophenyl)sulfonyl)(pyrimidin-2-yl)amido-κ2N,N′)-bis(μ2-4,4′-bipyridine-N,N′-κ2N:N′)zinc(II) – methanol (1/2), C32H34N10O6S2Zn
  25. Synthesis and crystal structure poly[aqua(μ3-2-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)acetate-κ4O,O′:O′′:O′′′) sodium] monohydrate, C18H18NNaO11S
  26. Crystal structure of methyl 4′-amino-3′,5′-diisopropyl-[1,1′-biphenyl]-4-carboxylate, C20H25NO2
  27. Crystal structure of (η6-1-isopropyl-4-methyl benzene)-(N-(2,5-dichlorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) perchlorate, C22H22Cl4N2O4Ru
  28. Crystal structure of 2-(2-(1-Chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1H-1,2,4-triazole-3(2H)-thione, C14H15Cl2N3OS
  29. Crystal structure of methyl 4′-amino-3′,5′-dimethyl-[1,1′-biphenyl]-4-carboxylate, C16H17NO2
  30. The crystal structure of 1-(5-ferrocenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pentan-1-on, C19H19F3FeN2O
  31. The crystal structure of (3S,12R,20R,24S)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25-triol acetone solvate, C34H56O6
  32. Crystal structure of methyl 10-(pyridin-4-yl)-anthracene-9-carboxylate, C21H15NO2
  33. Crystal structure of catena-poly[diaqua-bis(di(N2,N6-dihydroxypyridine-2,6-dicarboxamide))potassium(I)]tetrahydrate, C14H25N6O14K
  34. Crystal structure of poly{[μ2-(E)-1,4-bis(1H-benzo[d]imidazol-1-yl)but-2-ene-κ2N:N′][μ3–cyclohexane-1,4-dicarboxylato-κ4O,O′:O′′:O′′′]cadmium(II)}, C26H26CdN4O4
  35. Crystal structure of poly[aqua(μ3-[2,2′-bipyridine]-3,3′-dicarboxylato-κ4N,N′:O:O′)zinc(II)] – dimethylformamide (1/1), C15H15N3O6Zn
  36. The crystal structure of poly[tetraaqua-tris(μ2-2,6-di(1H-imidazol-1-yl)naphthalene-κ2N:N′)-bis(thiophene-2,5-dicarboxylato-κ1O)]dicobalt(II), C30H24CoN6O6S
  37. Crystal structure of (S)-1-(5-(anthracen-9-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O
  38. Crystal structure of 5-methyl-3,3-diphenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C25H25NO2S
  39. Synthesis and crystal structure of μ-[1,1′-di(mesitylphosphanido)ferrocene]bis[η5-cyclopentadienylnickel(II)] tetrahydrofurane solvate, C42H48FeNi2OP2
  40. Synthesis and crystal structure of (E)-1-(4-(((E)-5-chloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15ClN2O2
  41. Crystal structure of bis(1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O)nickel(II), C24H22N8O4S2Ni
  42. Crystal Structure of bis(1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O)copper(II), C24H22N8O4S2Cu
  43. Synthesis and crystal structure of poly[aqua{μ3-(1S,2S)-1-((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)pyrrolidin-1-ium-2-carboxylato-κ4O,O′:O′′:O′′′}sodium(I)] monohydrate, C21H22NNaO11S
  44. Halogen bonds in the crystal structure of 1,4-diiodotetrafluorobenzene–1,2-bis(4-pyridyl)propane (1/1), C19H14F4I2N2
  45. Crystal structure of bis(μ-N-i-propyl-N-n-propyldithiocarbamato-κ2S:S′) bis(N-i-propyl-N-n-propyldithiocarbamato-κ2S,S′)dizinc(II), C28H56N4S8Zn2
  46. Crystal structure of bis(μ-N-i-propyl-N-n-propyldithiocarbamato-κ3S,S′:S)bis(N-i-propyl-N-n-propyldithiocarbamato-κ2S,S′)dicadmium(II), C28H56Cd2N4S8
  47. Crystal structure of bis(μ2-di-n-butyldithiocarbamato-κ3S,S′:S;κ3S:S:S′)-hexacarbonyl-di-rhenium(I), C24H36N2O6Re2
  48. Crystal structure of 7-(4-methylphenyl)imidazo[1,2-a][1,3,5]triazin-4-amine, C12H11N5
  49. Crystal structure of the co-crystal O-isopropyl phenylcarbamothioate – 4,4′-bipyridine (2/1), C15H17N2OS
  50. Crystal structure of the coordination polymer catena-poly[chlorido-{μ2-2-(((3,5-dimethyl-1H-pyrazol-1-yl)methyl)amino)-3-hydroxybutanoato-κ4N,N,O:O′}copper(II)], C11H16ClCuN2O3
  51. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-di(ethanol)-bis{μ2-5-(N,N′-diethylamine)-5′-methoxyl-2,2′-[ethylenediyldioxybis(nitrilomethylidyne)]diphenolato-κ6O:O,N,N,O′:O′}trinickel(II) – ethanol – acetonitrile (1/2/2), C58H86Ni3N8O18
  52. Crystal structure of the bis((E)-O-ethyl-N-phenylthiocarbamate) – 4,4′-bipyridine co-crystal (2/1), C28H30N4O2S2
  53. Crystal structure of the (E)-O-methyl-N-phenyl-thiocarbamate – 4,4′-bipyridine (1/1), C18H17N3OS
  54. Crystal structure of bis(μ2-diethyldithiocarbamato-κ3S,S′:S′)-bis(tricyclohexylphosphane-κP)dicopper(I), C46H86Cu2N2P2S4
  55. Crystal structure of N-(3-chlorophenyl)ethoxycarbothioamide, C9H10ClNOS
  56. Crystal structure of bis(μ2-pyrrolidine-1-carbodithioato-κ3S,S′:S;κ3S:S:S′)-bis(tricyclohexylphosphane-P)-di-copper(I), C46H82Cu2N2P2S4
  57. Crystal structure of N-(2-chlorophenyl)methoxycarbothioamide, C8H8ClNOS
  58. Crystal structure of chlorido-methanol-(N-(2-(oxy)-3-methoxybenzylidene)pyridine-4-carbohydrazonato-κ3O,N,O′)-(4-methylphenyl)methyl-tin(IV), C23H24ClN3O4Sn
  59. Crystal structure of N-(3-chlorophenyl)(propan-2-yloxy)carbothioamide, C10H12ClNOS
  60. Crystal structure of 1-[(Z)-[4-(4-methoxyphenyl)butan-2-ylidene]amino]-3-phenylurea, C18H21N3O2
  61. A triclinic polymorph of bis(μ-N,N-bis(2-hydroxyethyl)dithiocarbamato-κ3S,S′:S′) bis(N,N-bis(2-hydroxyethyl)dithiocarbamato-κ2S:S′)zinc(II), C20H40N4O8S8Zn2
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