Startseite Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
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Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2

  • Qin Zhao EMAIL logo , Dong Lin , Yun Hou und Gui-Ge Hou
Veröffentlicht/Copyright: 9. September 2019
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 234 Heft 6

Abstract

C51H38Cl2F2N6O14S2, triclinic, P1̄ (no. 2), a = 11.8987(6) Å, b = 14.0939(8) Å, c = 16.1915(9) Å, α = 67.590(5)°, β = 75.402(5)°, γ = 77.522(4)°, V = 2407.3(2) Å3, Z = 2, Rgt(F) = 0.0584, wRref(F2) = 0.1645, T = 100.0(1) K.

CCDC no.: 1906806

The asymmetric unit of the title 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:Yellow block
Size:0.12 × 0.11 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.31 mm−1
Diffractometer, scan mode:SuperNova,
θmax, completeness:29.6°, >99%
N(hkl)measured, N(hkl)unique, Rint:20754, 11248, 0.028
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 8621
N(param)refined:694
Programs:CrysAlisPRO [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
C10.3285(2)0.59236(19)0.62774(17)0.0171(5)
H1A0.4067130.5574800.6135150.020*
H1B0.2732390.5429900.6475860.020*
C20.3219(2)0.63555(19)0.70138(17)0.0158(5)
C30.2338(2)0.72859(19)0.70366(18)0.0170(5)
C40.1496(2)0.76505(19)0.63950(18)0.0163(5)
C50.1757(2)0.7245(2)0.56201(18)0.0164(5)
H5A0.1266110.6715920.5759970.020*
H5B0.1583500.7803130.5071140.020*
C60.3921(2)0.59859(19)0.76293(18)0.0167(5)
H60.3824100.6349510.8021380.020*
C70.4828(2)0.50708(19)0.77592(17)0.0157(5)
C80.5844(2)0.5122(2)0.80113(18)0.0172(5)
H80.5930250.5709080.8109040.021*
C90.6723(2)0.4286(2)0.81140(18)0.0187(5)
C100.6615(2)0.3368(2)0.80315(18)0.0199(6)
H100.7211930.2812030.8119960.024*
C110.5585(2)0.3309(2)0.78125(18)0.0190(5)
H110.5480050.2698390.7764010.023*
C120.4709(2)0.4150(2)0.76648(17)0.0168(5)
H120.4033960.4103300.7500760.020*
C130.0548(2)0.83261(19)0.65495(18)0.0172(5)
H130.0499030.8514520.7050190.021*
C14−0.0418(2)0.88096(19)0.60503(17)0.0162(5)
C15−0.0682(2)0.8488(2)0.54095(18)0.0176(5)
H15−0.0234250.7921400.5271020.021*
C16−0.1622(2)0.9030(2)0.49853(18)0.0190(5)
C17−0.2337(2)0.9871(2)0.5168(2)0.0208(6)
H17−0.2952721.0223470.4863300.025*
C18−0.2096(2)1.0163(2)0.5819(2)0.0215(6)
H18−0.2570341.0711980.5971510.026*
C19−0.1157(2)0.9650(2)0.62506(19)0.0182(5)
H19−0.1009920.9867620.6683960.022*
C200.2633(2)0.5944(2)0.43145(17)0.0166(5)
C210.2977(2)0.4880(2)0.45398(19)0.0207(6)
H210.3661070.4571780.4768390.025*
C220.2287(3)0.4293(2)0.4418(2)0.0261(6)
H220.2501490.3582880.4555160.031*
C230.1275(3)0.4777(3)0.4090(2)0.0274(7)
C240.0912(3)0.5828(3)0.3868(2)0.0276(7)
H240.0218180.6126260.3651500.033*
C250.1608(2)0.6423(2)0.39769(19)0.0225(6)
H250.1395320.7134520.3826600.027*
C260.6508(2)0.77958(19)0.99781(18)0.0166(5)
H26A0.6445560.7693701.0614410.020*
H26B0.7332650.7766750.9701300.020*
C270.6019(2)0.6920(2)0.99134(17)0.0156(5)
C280.4854(2)0.7147(2)0.96240(18)0.0166(5)
C290.4122(2)0.81629(19)0.96007(17)0.0157(5)
C300.4627(2)0.8900(2)0.98407(18)0.0170(5)
H30A0.4272530.9603090.9557970.020*
H30B0.4441760.8738151.0494330.020*
C310.6539(2)0.59328(19)1.01301(17)0.0153(5)
H310.6158770.5484531.0032320.018*
C320.7614(2)0.54555(19)1.04973(17)0.0155(5)
C330.8092(2)0.44626(19)1.04741(17)0.0165(5)
H330.7735220.4138151.0223850.020*
C340.9094(2)0.3968(2)1.08246(18)0.0181(5)
C350.9648(2)0.4394(2)1.12283(19)0.0216(6)
H351.0314830.4039051.1467650.026*
C360.9175(2)0.5370(2)1.1263(2)0.0231(6)
H360.9529920.5679591.1527600.028*
C370.8177(2)0.5890(2)1.09093(19)0.0191(5)
H370.7872600.6542191.0944540.023*
C380.3091(2)0.83801(19)0.93303(18)0.0172(5)
H380.2895680.7883080.9163210.021*
C390.2232(2)0.93215(19)0.92683(18)0.0164(5)
C400.1564(2)0.9673(2)0.85843(18)0.0174(5)
H400.1654950.9318870.8185360.021*
C410.0766(2)1.0559(2)0.85170(18)0.0183(5)
C420.0588(2)1.1118(2)0.90948(19)0.0203(6)
H420.0058001.1722170.9019180.024*
C430.1227(2)1.0746(2)0.97870(19)0.0194(6)
H430.1116601.1095311.0192230.023*
C440.2034(2)0.9851(2)0.98795(18)0.0175(5)
H440.2447680.9601991.0353740.021*
C450.6177(2)0.8921(2)0.77609(18)0.0187(5)
C460.6962(2)0.8088(2)0.76228(18)0.0198(5)
H460.7606290.7832610.7908740.024*
C470.6767(3)0.7642(2)0.70494(19)0.0222(6)
H470.7274320.7078310.6948570.027*
C480.5812(3)0.8049(2)0.6634(2)0.0253(6)
C490.5014(3)0.8866(2)0.6773(2)0.0272(6)
H490.4365300.9109840.6491800.033*
C500.5207(2)0.9317(2)0.73432(19)0.0240(6)
H500.4692070.9877610.7444610.029*
C510.6996(3)0.7302(3)0.3190(3)0.0393(8)
H51A0.6384140.6885750.3574810.047*
H51B0.7184450.7657570.3535780.047*
Cl10.64805(8)0.82089(7)0.22466(7)0.0446(2)
Cl20.82525(8)0.64819(7)0.28940(7)0.0454(2)
F10.06066(17)0.41963(16)0.39576(14)0.0409(5)
F20.56466(17)0.76282(15)0.60517(13)0.0364(5)
N10.29952(18)0.68065(16)0.54724(15)0.0157(4)
N20.7835(2)0.43892(19)0.82920(17)0.0250(5)
N3−0.1891(2)0.86664(19)0.43283(18)0.0257(5)
N40.59040(19)0.88264(16)0.95335(15)0.0166(4)
N50.0046(2)1.09108(18)0.78081(17)0.0232(5)
N60.9613(2)0.29491(17)1.07519(16)0.0213(5)
O10.22913(17)0.77193(15)0.75744(13)0.0219(4)
O20.33192(17)0.77294(14)0.38099(13)0.0215(4)
O30.46790(15)0.61664(14)0.44778(13)0.0188(4)
O40.8588(2)0.36308(18)0.84322(19)0.0411(6)
O50.79632(19)0.52369(17)0.82756(17)0.0329(5)
O6−0.13104(19)0.78789(15)0.42119(15)0.0289(5)
O7−0.2704(2)0.91683(19)0.39251(17)0.0386(6)
O80.45046(17)0.65123(14)0.94342(14)0.0233(4)
O90.76788(17)0.93781(16)0.84201(14)0.0253(4)
O100.57626(19)1.04971(14)0.82985(14)0.0259(5)
O110.91975(18)0.26238(15)1.03116(15)0.0276(5)
O121.04559(18)0.24864(16)1.11218(15)0.0305(5)
O130.02287(19)1.04271(16)0.72889(15)0.0280(5)
O14−0.0694(2)1.16705(18)0.77640(17)0.0391(6)
S10.35120(5)0.67091(5)0.44594(4)0.01573(15)
S20.64384(6)0.94941(5)0.84852(4)0.01867(15)

Source of material

The raw material 3-nitrobenzaldehyde (1.51 mol, 10.0 mmol) and 4-piperidone hydrate hydrochloride (0.77 g, 5.0 mmol) were added to a solution with 25 mL acetic acid. Dry HCL gas was passed through the solution about 25 min. After stirring at room temperature overnight, the mixture produced a precipitate. The precipitate was filtered and washed by acetone to get a yellow intermediate. Then, the intermediate, 4-fluorobenzenesulfonylchloride (0.62 g, 5.0 mol) and potassium carbonate (2.76 g, 0.02 mol) were added to 50 mL of dichloromethane. The mixture was stirred for about 12 h at room temperature. The precipitate was collected, washed with water and recrystallized from dichloromethane/methanol (2:3, v/v) to get light yellow crystals of the title compound.

Experimental details

All H atoms were placed in idealized positions and treated as riding on their parent atoms, with d(C—H) = 0.97 Å (methylene), Uiso(H) = 1.2Ueq(C) and d(C—H) = 0.93 Å (aromatic), Uiso(H) = 1.2Ueq(C).

Comment

Curcumin, is a yellow pigment extracted from the rhizome of turmeric, which has been extensively investigated for its anti-tumor, anti-inflammatory activity, anti-oxidation and other activities. However, its clinical application was limited due to its poor aqueous solubility, relatively low bioactivities and bioavailability [4]. In order to improve these weakness, many curcumin analogs were previously synthesized as better antitumor and anti-inflammatory agents, such as 3E,5E)-3,5-bis(arylidene)-4-piperidones (BAPs) [5], [6]. In our previous study, we found BAPs have greater predilection or sequential interaction for bio-thiols resulting in a greater activity to tumors rather than with normal cells [7].

In order to improve its biological activity, strong electron-withdrawing substituent groups (Such as -NO2, -CN, -CF3) were introduced on both sides of BAPs. While some electron-withdrawing trifluoromethyl groups (Such as -F, -NO2, -CN, -CF3) were introduced into N-benzenesulfonyl substituents of BAPs. By introducing these groups, the antitumor and anti-inflammatory activity of BAPs should be improved, while toxicity should be reduced to different degrees [8].

Crystal structure and bioactivity of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile (BAP-1) and (3E,5E)-3,5-bis(4-cyanobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one (BAP-2) were reported by our group [9], [10]. Recently, we found that the antitumor and anti-inflammatory activity were improved when fluorine was substituted on N-benzenesulfonyl substituents of BAPs. Herein, the crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one-dichloromethane(2/1) will be reported.

There are two BAP molecules and a dichloromethane molecule in the asymmetric unit of the title compound (cf. the figure). Bond lengths and angles are all in the expected ranges. Single-crystal structure analysis reveals that configurations of the two BAPs molecules are different. In a molecule, two 3-nitro phenyl groups on both sides of BAP take the trans-configuration compared with the central piperidin-4-one. And the two 3-nitro phenyl groups adopt the E stereochemistry of olefinic double bonds, which was the same as those reported in literature [10]. In the other molecule, two 3-nitro phenyl groups are symmetric compared with central piperidin-4-one, which also adopt the E stereochemistry of the double bond. The dihedral angles between two 4-nitro phenyl groups in both molecules are 32.61(6)° and 26.36(3)°, respectively. Interestingly, the 4-trifluoromethylphenyl group bend towards the side of carbonyl group in one molecule, which looks like an “organic clip” [10], however, 4-trifluoromethylphenyl group stretch in the other direction of carbonyl group in another molecule. The peripheric heteroatoms (Such as F, N, O, S) can act as hydrogen bonding acceptors for bioactive molecules with the aim of creating more potent biological activity [11], [12].

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 81601049

Funding source: Key R & D project of Shandong Province

Award Identifier / Grant number: 2018YYSP009

Funding source: Shandong Provincial Medicine and Health Technology Development Plan

Award Identifier / Grant number: 2017WSB290215

Funding statement: This work was supported by the National Natural Science Foundation of China (no. 81601049), Key R & D project of Shandong Province (No. 2018YYSP009) and Shandong Provincial Medicine and Health Technology Development Plan (No. 2017WSB290215).

References

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3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

4. Nelson, K. M.; Dahlin, J. L.; Bisson, J.; Graham, J.; Pauli, G. F.; Walters, M. A.: The essential medicinal chemistry of curcumin. J. Med. Chem. 60 (2017) 1620–1637.10.1021/acs.jmedchem.6b00975Suche in Google Scholar PubMed PubMed Central

5. Zhang, L. S.; Chen, Q.; Hou, G. G.; Zhao, W.; Hou, Y.: Hydroxyl-substituted double Schiff-base condensed 4-piperidone/cyclohexanones as potential anticancer agents with biological evaluation. J. Enzyme Inhib. Med. Chem. 34 (2019) 264–271.10.1080/14756366.2018.1501042Suche in Google Scholar PubMed PubMed Central

6. Li, N.; Xin, W. Y.; Yao, B. R.; Cong, W.; Wang, C. H.; Hou, G. G.: N-phenylsulfonyl-3,5-bis(arylidene)-4-piperidone derivatives as activation NF-κB inhibitors in hepatic carcinoma cell lines. Eur. J. Med. Chem. 155 (2018) 531–544.10.1016/j.ejmech.2018.06.027Suche in Google Scholar PubMed

7. Yao, B. R.; Li, N.; Wang, C. H.; Hou, G. G.; Meng, Q. G.; Yan, K.: Novel asymmetric 3,5-bis(arylidene)piperidin-4-one derivatives: synthesis, crystal structures and cytotoxicity. Acta Crystallogr. C74 (2018) 659–665.10.1107/S2053229618006605Suche in Google Scholar PubMed

8. Yao, B. R.; Sun, Y.; Chen, S. L.; Suo, H. D.; Zhang, Y. L.; Wei, H.; Wang, C. H.; Zhao, F.; Cong, W.; Xin, W. Y.; Hou, G. G.: Dissymmetric pyridyl-substituted 3,5-bis(arylidene)-4-piperidones as anti-hepatoma agents by inhibiting NF-kB pathway activation. Eur. J. Med. Chem. 167 (2019) 187–199.10.1016/j.ejmech.2019.02.020Suche in Google Scholar PubMed

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Received: 2019-05-26
Accepted: 2019-08-05
Published Online: 2019-09-09
Published in Print: 2019-11-26

©2019 Qin Zhao 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

  1. Frontmatter
  2. Crystal structure of [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′] zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
  5. Crystal structure of 4,4′-(hydrazonomethylene)diphenol dihydrate, C13H16N2O4
  6. Crystal structure of 4-methoxyphenyl-3-phenylpropiolate, C16H12O3
  7. Crystal Structure of tris(tetrakis{1-vinyl-1H-imidazole-κN}copper(II)) bis[tri-μ2-bromido-tetrabromido-bis(1-vinyl-1H-imidazole-κN)tetracopper(I)], C80H96N32Cu11Br14
  8. Crystal structure of (E)-2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)-N′-(quinoxalin-2-ylmethylene)benzohydrazide, C37H36N6O2
  9. Crystal structure of 4-(1-phenylimidazo[1,5-a]pyridin-3-yl)benzoic acid (C20H14N2O2)
  10. Crystal structure of 3-fluoro-3-methyl-1-((2-nitrophenyl)sulfonyl)-5,5-diphenylpiperidine, C24H23FN2O4S
  11. Crystal structure of dimethyl 3,12-dibenzyl-6,10-diphenyl-3,12-diazapentacyclo [6.3.1.02.7.04.11.05.9]-dodecane-7,11-dicarboxylate — acetone (2/1), C40H38N2O2 ⋅ 0.5C3H6O
  12. Crystal structure of poly[(μ2-2-(1H-1,2,4-triazol-1-yl)benzoato-κ4O:O′:N:N′)silver(I)] monohydrate, C9H8AgO3N3
  13. Crystal structure of poly[(μ2-9H-carbazole-3,6-dicarboxylate-κ4O1,O2:O3,O4)(μ2-1,3-di(pyridin-4-yl)propane-κ2N:N′)cadmium(II)]monohydrate, C27H23N3O5Cd
  14. The synthesis and crystal structure of bis(2-(benzo[d]thiazol-2-yl)-5-methylbenzen-1-ido-κ2C,N)-(N,N′-diethyldithiocarbamato-κ2S,S′)iridium(III), C33H30N3S4Ir
  15. The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
  16. Synthesis and crystal structure of poly[(μ2-nitrato-κ4O,O′:O′,O′′)-nitrato-κO-(μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)cadmium(II)], C14H14N6O6Cd
  17. Crystal structure of ethyl (Z)-(4-oxo-4-phenylbut-2-en-2-yl)glycinate, C14H17NO3
  18. Halogen bonds in the crystal structure of 5-bromo-3,4′-bipyridine – 1,4-diiodotetrafluorobenzene (2/1), C26H14Br2F4I2N4
  19. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-tetrakis(μ2-3-(phenylsulfonamido)propanoato-κ2O:O′)-bis(3-(phenylsulfonamido)propanoato-κ2O,O′)digadolinium(III) – 2,2′-bipyridine (1/1), C84H84Gd2N12O24S6
  20. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ2O:O′)bis(μ2-pyrazin-κ2N:N′)silver(I)], C14H16Ag2N5O8S2
  21. The crystal structure of 1,6-di-tert-butyl-1,1,3,3,4,4,6,6-octamethyl-2,2,5,5-tetrakis (trimethylsilyl)hexasilane, C28H78Si10
  22. Crystal structure of discandium triruthenium tetrasilicide, Sc2Ru3Si4
  23. Crystal structure of poly[(μ2-4-amino-1,5-naphthalenedisulfonato-κ4O,N:O′, N′)bis(μ2-hexamethylenetetramino-κ2N;N′)silver(I)], {C22H30Ag2N9O6S2}n
  24. Crystal structure of diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-κ4O,O′,N,N′)]zinc(II) dihydrate, C13H18N4O12Zn
  25. The crystal structure of poly [(μ3-N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide-κ3-O:N:N′)-(p-toluenesulfonato-κ2O,O′)silver(I)], C25H27Ag1N4O5S
  26. The crystal structure of 1,2-bis(3-bromophenoxy) ethane, C14H12Br2O2
  27. The crystal structure of 4-(pyren-1-yl)butyl-3-nitrobenzoate, C27H21NO4
  28. Crystal structure of bis[(2-(4-chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ1O) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Cl2N4NiO8
  29. The crystal structure of 1,5-dinitro-2,3,4-trichlorobenzene, C6H1Cl3N2O4
  30. The crystal structure of the solid solution of 3,5-dinitropyrazole and 4-chlorine-3,5-dinitropyrazole, C3H1.24Cl0.76N4O4
  31. The cocrystal structure of 4-nitropyrazole — acetic acid (1/1), C5H7N3O4
  32. The crystal structure of propan-2-one O-(2,4,6-trinitrophenyl) oxime, C9H8N4O7
  33. The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
  34. Crystal structure of (acetic acid-κ1O)-bis(μ2-2-chlorobenzoato-κ2O:O′)-(2-chlorobenzoato-κ1O)-(μ2-hydroxy-κ2O:O)-bis(1,10-phenanthroline-κ2N,N′)dimanganese(II) — methanol (1/1), C48H37Cl3Mn2N4O10
  35. Crystal structure of 3-methyl-2-phenyl-1,8-naphthyridine, C15H12N2
  36. Crystal structure of chlorido-(5-acetyl-2-(5-methylpyridin-2-yl)benzen-1-ido-κ2C,N)-pyridine-κN-palladium(II), C19H17ClN2OPd
  37. Crystal structure of (4-methyl-benzoato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C24H45ClN4NiO7
  38. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) 1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl(potassium, rubidium) — ammonia (1/2), [K0.3Rb0.7(18-crown-6)]Cp*⋅2 NH3, C22H45K0.3N2O6Rb0.7
  39. Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
  40. Crystal structure of (E)-N′-((1,6-dihydropyren-1-yl)methylene)isonicotinohydrazide — methanol (1/1), C24H19N3O2
  41. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ3N,O:O′)-(μ4-hexamethylenetetramino-κ4N:N′:N′′:N′′′)disilver(I)] monohydrate, C12H21Ag2N5O8S2
  42. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
https://doi.org/10.1515/ncrs-2019-0369
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Artikel in diesem Heft

  1. Frontmatter
  2. Crystal structure of [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′] zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
  5. Crystal structure of 4,4′-(hydrazonomethylene)diphenol dihydrate, C13H16N2O4
  6. Crystal structure of 4-methoxyphenyl-3-phenylpropiolate, C16H12O3
  7. Crystal Structure of tris(tetrakis{1-vinyl-1H-imidazole-κN}copper(II)) bis[tri-μ2-bromido-tetrabromido-bis(1-vinyl-1H-imidazole-κN)tetracopper(I)], C80H96N32Cu11Br14
  8. Crystal structure of (E)-2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)-N′-(quinoxalin-2-ylmethylene)benzohydrazide, C37H36N6O2
  9. Crystal structure of 4-(1-phenylimidazo[1,5-a]pyridin-3-yl)benzoic acid (C20H14N2O2)
  10. Crystal structure of 3-fluoro-3-methyl-1-((2-nitrophenyl)sulfonyl)-5,5-diphenylpiperidine, C24H23FN2O4S
  11. Crystal structure of dimethyl 3,12-dibenzyl-6,10-diphenyl-3,12-diazapentacyclo [6.3.1.02.7.04.11.05.9]-dodecane-7,11-dicarboxylate — acetone (2/1), C40H38N2O2 ⋅ 0.5C3H6O
  12. Crystal structure of poly[(μ2-2-(1H-1,2,4-triazol-1-yl)benzoato-κ4O:O′:N:N′)silver(I)] monohydrate, C9H8AgO3N3
  13. Crystal structure of poly[(μ2-9H-carbazole-3,6-dicarboxylate-κ4O1,O2:O3,O4)(μ2-1,3-di(pyridin-4-yl)propane-κ2N:N′)cadmium(II)]monohydrate, C27H23N3O5Cd
  14. The synthesis and crystal structure of bis(2-(benzo[d]thiazol-2-yl)-5-methylbenzen-1-ido-κ2C,N)-(N,N′-diethyldithiocarbamato-κ2S,S′)iridium(III), C33H30N3S4Ir
  15. The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
  16. Synthesis and crystal structure of poly[(μ2-nitrato-κ4O,O′:O′,O′′)-nitrato-κO-(μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)cadmium(II)], C14H14N6O6Cd
  17. Crystal structure of ethyl (Z)-(4-oxo-4-phenylbut-2-en-2-yl)glycinate, C14H17NO3
  18. Halogen bonds in the crystal structure of 5-bromo-3,4′-bipyridine – 1,4-diiodotetrafluorobenzene (2/1), C26H14Br2F4I2N4
  19. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-tetrakis(μ2-3-(phenylsulfonamido)propanoato-κ2O:O′)-bis(3-(phenylsulfonamido)propanoato-κ2O,O′)digadolinium(III) – 2,2′-bipyridine (1/1), C84H84Gd2N12O24S6
  20. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ2O:O′)bis(μ2-pyrazin-κ2N:N′)silver(I)], C14H16Ag2N5O8S2
  21. The crystal structure of 1,6-di-tert-butyl-1,1,3,3,4,4,6,6-octamethyl-2,2,5,5-tetrakis (trimethylsilyl)hexasilane, C28H78Si10
  22. Crystal structure of discandium triruthenium tetrasilicide, Sc2Ru3Si4
  23. Crystal structure of poly[(μ2-4-amino-1,5-naphthalenedisulfonato-κ4O,N:O′, N′)bis(μ2-hexamethylenetetramino-κ2N;N′)silver(I)], {C22H30Ag2N9O6S2}n
  24. Crystal structure of diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-κ4O,O′,N,N′)]zinc(II) dihydrate, C13H18N4O12Zn
  25. The crystal structure of poly [(μ3-N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide-κ3-O:N:N′)-(p-toluenesulfonato-κ2O,O′)silver(I)], C25H27Ag1N4O5S
  26. The crystal structure of 1,2-bis(3-bromophenoxy) ethane, C14H12Br2O2
  27. The crystal structure of 4-(pyren-1-yl)butyl-3-nitrobenzoate, C27H21NO4
  28. Crystal structure of bis[(2-(4-chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ1O) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Cl2N4NiO8
  29. The crystal structure of 1,5-dinitro-2,3,4-trichlorobenzene, C6H1Cl3N2O4
  30. The crystal structure of the solid solution of 3,5-dinitropyrazole and 4-chlorine-3,5-dinitropyrazole, C3H1.24Cl0.76N4O4
  31. The cocrystal structure of 4-nitropyrazole — acetic acid (1/1), C5H7N3O4
  32. The crystal structure of propan-2-one O-(2,4,6-trinitrophenyl) oxime, C9H8N4O7
  33. The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
  34. Crystal structure of (acetic acid-κ1O)-bis(μ2-2-chlorobenzoato-κ2O:O′)-(2-chlorobenzoato-κ1O)-(μ2-hydroxy-κ2O:O)-bis(1,10-phenanthroline-κ2N,N′)dimanganese(II) — methanol (1/1), C48H37Cl3Mn2N4O10
  35. Crystal structure of 3-methyl-2-phenyl-1,8-naphthyridine, C15H12N2
  36. Crystal structure of chlorido-(5-acetyl-2-(5-methylpyridin-2-yl)benzen-1-ido-κ2C,N)-pyridine-κN-palladium(II), C19H17ClN2OPd
  37. Crystal structure of (4-methyl-benzoato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C24H45ClN4NiO7
  38. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) 1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl(potassium, rubidium) — ammonia (1/2), [K0.3Rb0.7(18-crown-6)]Cp*⋅2 NH3, C22H45K0.3N2O6Rb0.7
  39. Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
  40. Crystal structure of (E)-N′-((1,6-dihydropyren-1-yl)methylene)isonicotinohydrazide — methanol (1/1), C24H19N3O2
  41. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ3N,O:O′)-(μ4-hexamethylenetetramino-κ4N:N′:N′′:N′′′)disilver(I)] monohydrate, C12H21Ag2N5O8S2
  42. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
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