Startseite Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-acetamidophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one-methanol-hydrate (2/1/1), C53H50F2N6O10S2
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Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-acetamidophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one-methanol-hydrate (2/1/1), C53H50F2N6O10S2

  • An-Qi Wang , Ru-Ning Gao , Qing-Hao Luan , Ze-Ping Wang , Xiao-Ming Li und Gui-Ge Hou ORCID logo EMAIL logo
Veröffentlicht/Copyright: 9. November 2019
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 235 Heft 2

Abstract

C53H50F2N6O10S2, monoclinic, P21/n (no. 14), a = 15.088(5) Å, b = 23.560(9) Å, c = 15.401(6) Å, β = 112.254(5)°, V = 5067(3) Å3, Z = 4, Rgt(F) = 0.0509, wRref(F2) = 0.1336, T = 298(2) K.

CCDC no.: 1868649

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:Yellow block
Size:0.15 × 0.12 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.18 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:27.5°, 99%
N(hkl)measured, N(hkl)unique, Rint:28143, 11167, 0.047
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 6078
N(param)refined:664
Programs:CrysAlisPRO [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
C10.97818(14)0.15423(9)0.39036(17)0.0486(6)
H1A1.0047990.1614770.3431260.058*
H1B1.0194580.1270370.4345820.058*
C20.97799(14)0.20896(9)0.44160(15)0.0429(5)
C30.89913(14)0.21956(9)0.47478(17)0.0464(5)
C40.81519(14)0.18021(9)0.44418(15)0.0428(5)
C50.83011(15)0.12332(9)0.40706(17)0.0516(6)
H5A0.8655350.0987010.4591470.062*
H5B0.7684530.1058470.3729060.062*
C61.04463(15)0.24978(9)0.45864(16)0.0483(6)
H61.0323400.2823660.4862780.058*
C71.13302(15)0.25156(10)0.44107(17)0.0512(6)
C81.1754(2)0.30298(12)0.4388(2)0.0818(9)
C91.2606(2)0.30923(14)0.4279(3)0.1062(12)
H91.2860650.3450680.4270670.127*
C101.3072(2)0.26164(15)0.4184(2)0.0928(10)
H101.3648810.2647500.4099580.111*
C111.26974(18)0.20974(13)0.4212(2)0.0789(9)
H111.3021420.1773470.4151340.095*
C121.18477(16)0.20458(11)0.43294(19)0.0625(7)
H121.1609060.1684930.4355490.075*
C130.73203(14)0.19992(10)0.44364(15)0.0487(6)
H130.7328950.2370890.4642740.058*
C140.63944(15)0.17069(10)0.41479(16)0.0496(6)
C150.55659(16)0.20101(11)0.36297(19)0.0621(7)
H150.5635760.2385000.3477590.075*
C160.46006(18)0.12636(13)0.3595(2)0.0700(8)
H160.3990080.1108630.3413550.084*
C170.53654(18)0.09324(12)0.41103(19)0.0657(7)
H170.5272160.0564510.4277860.079*
C180.62758(16)0.11539(11)0.43758(17)0.0568(6)
H180.6806170.0931740.4706380.068*
C190.78102(14)0.21005(9)0.21268(15)0.0442(5)
C200.84062(15)0.25315(10)0.20470(17)0.0541(6)
H200.9033300.2450400.2118510.065*
C210.80656(15)0.30754(10)0.18627(17)0.0548(6)
H210.8467710.3362000.1813200.066*
C220.71303(14)0.32068(9)0.17484(15)0.0450(5)
C230.65428(14)0.27787(10)0.18448(16)0.0489(6)
H230.5918820.2860380.1783400.059*
C240.68874(14)0.22324(9)0.20318(16)0.0485(6)
H240.6490350.1947000.2095250.058*
C250.59699(17)0.40152(11)0.13364(16)0.0531(6)
C260.59411(18)0.46398(11)0.11424(19)0.0684(7)
H26A0.6018180.4702630.0559140.103*
H26B0.6449830.4825090.1640080.103*
H26C0.5336890.4791610.1103870.103*
C270.48584(14)0.52801(9)0.32655(16)0.0482(6)
H27A0.5257330.5559520.3701800.058*
H27B0.5135080.5206020.2801620.058*
C280.48671(14)0.47356(9)0.37946(15)0.0422(5)
C290.40569(15)0.46202(9)0.41027(16)0.0475(6)
C300.32475(15)0.50320(9)0.38465(15)0.0445(5)
C310.33812(16)0.55927(9)0.34260(16)0.0504(6)
H31A0.2759550.5760480.3080880.060*
H31B0.3737350.5851530.3926300.060*
C320.55540(15)0.43366(9)0.40054(15)0.0475(6)
H320.5425340.4011850.4280470.057*
C330.64581(15)0.43222(9)0.38809(15)0.0463(5)
C340.69202(18)0.38031(10)0.39275(17)0.0580(6)
C350.77977(19)0.37374(12)0.38917(18)0.0652(7)
H350.8069160.3379370.3928470.078*
C360.82739(19)0.42167(13)0.37994(18)0.0695(8)
H360.8878200.4184840.3774470.083*
C370.78652(17)0.47386(11)0.37440(18)0.0628(7)
H370.8192300.5059570.3676650.075*
C380.69760(15)0.47964(10)0.37866(16)0.0514(6)
H380.6713030.5156650.3752180.062*
C390.24452(15)0.48643(10)0.39359(16)0.0511(6)
H390.2462900.4503060.4185270.061*
C400.15351(15)0.51695(10)0.36962(16)0.0488(6)
C410.06843(17)0.48632(11)0.33016(18)0.0625(7)
H410.0727450.4475420.3211350.075*
C42−0.02342(18)0.56388(13)0.3229(2)0.0692(8)
H42−0.0836320.5802220.3069320.083*
C430.05577(17)0.59765(11)0.36404(18)0.0623(7)
H430.0491260.6356250.3768930.075*
C440.14484(16)0.57419(10)0.38578(17)0.0548(6)
H440.1992970.5966470.4113200.066*
C450.28154(14)0.46559(9)0.16693(15)0.0449(5)
C460.33941(15)0.41873(10)0.17018(16)0.0491(6)
H460.4011040.4238870.1717380.059*
C470.30459(15)0.36499(10)0.17106(16)0.0516(6)
H470.3435750.3339550.1736030.062*
C480.21210(15)0.35574(10)0.16824(16)0.0505(6)
C490.15540(15)0.40318(11)0.16609(17)0.0566(6)
H490.0938370.3982230.1649900.068*
C500.19014(15)0.45693(10)0.16559(16)0.0521(6)
H500.1517750.4880550.1643350.063*
C510.0938(2)0.28025(13)0.1597(2)0.0835(9)
C520.0826(2)0.21698(13)0.1502(3)0.1094(12)
H52A0.1163880.1994930.2099920.164*
H52B0.1082780.2036450.1056580.164*
H52C0.0158980.2073370.1289450.164*
C530.8690(3)0.44374(17)0.0881(3)0.1349(16)
H53A0.8783860.4798110.0638210.202*
H53B0.8227490.4220880.0388050.202*
H53C0.9286210.4234960.1118730.202*
F11.12899(14)0.35016(7)0.44754(19)0.1410(9)
F20.64508(11)0.33292(6)0.40313(13)0.0896(5)
N10.88272(11)0.12931(7)0.34497(13)0.0463(5)
N20.46826(13)0.17974(10)0.33394(16)0.0693(6)
N30.68449(12)0.37711(8)0.15384(15)0.0536(5)
H30.7247850.4019550.1613300.080*
N40.38959(12)0.55156(7)0.27936(13)0.0441(4)
N5−0.01847(14)0.50905(11)0.30461(16)0.0704(6)
N60.18053(13)0.30004(9)0.16414(16)0.0617(6)
H6A0.2131540.2734200.1588750.092*
O10.90128(11)0.26020(7)0.52570(12)0.0628(5)
O20.74164(11)0.10352(7)0.20780(12)0.0683(5)
O30.89140(11)0.13353(7)0.18982(12)0.0655(5)
O40.52587(12)0.37452(8)0.12825(14)0.0758(6)
O50.40497(11)0.41958(7)0.45555(13)0.0656(5)
O60.24555(11)0.57241(7)0.14147(11)0.0619(5)
O70.39125(11)0.53481(7)0.12321(12)0.0629(5)
O80.03128(15)0.31082(10)0.1641(2)0.1393(11)
O90.81749(11)0.28359(7)0.66190(14)0.0796(6)
H9A0.8591970.2895000.7172910.119*
H9B0.8454290.2750900.6250920.119*
O100.83559(15)0.45229(11)0.16088(18)0.0994(7)
H10A0.8754700.4703540.2033130.149*
S10.82334(4)0.14006(2)0.23271(4)0.05086(17)
S20.32634(4)0.53468(2)0.17088(4)0.04829(16)

Source of material

2-Fluorobenzaldehyde (1.24 g, 10.0 mmol), 3-pyridinecarboxaldehyde (1.07 g, 10.0 mmol) and 4-piperidone hydrate hydrochloride (1.35 g, 10.0 mmol), were mixed in a solution of acetic acid (20 mL). Dry HCl gas was passed through this mixture for 30 min. After stirring at room temperature for about 24 h [monitored by thin-layer chromatography (TLC)], the precipitate was collected and washed with cold acetone. The precipitate was added to 100 mL water; an aqueous Na2CO3 solution was then added until the pH value was adjusted to about 7. The precipitate was filtered, subsequently washed by water, and purified on silica gel by column chromatography using methanol/petroleum ether/EtOAc (1:10:10, v/v/v) as the eluent to afford a yellow intermediate. Next, the intermediate (0.59 g, 2.0 mmol), and 4-acetamidobenzenesulfonyl chloride (0.51 g, 2.2 mmol) were dissolved in a solution of dichloromethane (50 mL). Two drops of pyridine were added to the mixture. After stirring for about 6 h at room temperature, the precipitate was collected, washed with water and recrystallized from dichloromethane/methanol (1:1, v/v) to yield light yellow crystals of title compound.

The anti-inflammatory activities of title compound were evaluated by inhibition of LPS-induced NO secretion on mouse RAW264.7 macrophages. Pyrrolidine dithiocarbamate (PDTC) was used as a reference standard. In preliminary experiments, the title compound had no significant toxicity at 6.0 M on RAW264.7 cells. RAW264.7 cells were pretreated with 30 M of PDTC or with 6.0 M of title compound for 2.0 h. After treatment with LPS (1.0 g/mL) for 22 h, the collected culture media were centrifuged at 1000 rpm for 10 min. The expression levels of NO secretion in the media were determined by ELISA with an ELISA kit (eBioScience, San Diego, CA). The experiment was carried out in triplicate.

Experimental details

The H atoms of water, methanol (O—H) and acetylamino group (N—H) were located in a difference Fourier map and included as riding atoms, with d(O—H) = 0.85 Å, Uiso(H) = 1.5Ueq(O, water), and d(O—H) = 0.82 Å, Uiso(H) = 1.5Ueq(O, methanol), and d(N—H) = 0.82 Å, Uiso(H) = 1.5Ueq(N, acetylamino). Other H atoms were placed in idealized positions and treated as riding on their parent atoms, with d(C—H) = 0.96 Å (methyl), Uiso(H) = 1.5Ueq(C), and 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

In order to overcome low bioactivities, poor aqueous solubility and false positive problem of curcumin [4], a series of novel curcumin analogues have been reported, such as 3E,5E)-3,5-bis(arylidene)-4-piperidone derivatives (BAPs). BAPs contain two α,β-unsaturated keto groups, and show greater predilection or sequential interaction for bio-thiols in tumors rather than normal cell [5], [6]. In previous study, some BAPs were reported as better antitumor and anti-inflammatory agents [7], [8], [9]. Some strong electron-withdrawing substituent groups (Such as –NO2, –CN, –CF3) were assigned to both sides of BAPs. Their antitumor and anti-inflammatory activity were improved to different extent. Some crystal structure and bioactivity of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile (BAP-1), (3E,5E)-3,5-bis(4-cyanobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one (BAP-2), (3E,5E)-3,5-bis(3-nitrobenzylidene)-1-((4-(trifluoromethyl) phenyl)sulfonyl)piperidin-4-one (BAP-3) were reported [10], [11], [12].

When changing one side of BAPs to 3-pyridine substituents, while another side of BAPs is 2-F group, dissymmetric BAPs could be generated [8]. By adding the N-phenylsulfonyl moiety [13], the desired and improved antitumor activities and anti-inflammatory activity of BAPs could be found. In this study, we report the crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-acetamidophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one.

Single-crystal structure analysis reveals that there are two BAP molecules, a methanol and a water molecule in the asymmetric unit of the title crystal structure (cf. the figure). Bond lengths and angles are all in the expected ranges. The central 3,5-bis(arylidene)-4-piperidone scaffold is lengthened on both sides in a linear fashion, with the pyridyl and arylidene substituents adopting the E stereochemistry of the olefinic double bonds [14], [15]. The dihedral angles between the pyridyl and central piperidone rings of the symmetry independent molecules are 57.5(3)° and 50.1(4)°, while the dihedral angles between arylidene and central piperidone are 24.1(3)° and 22.5(2)°, respectively. In addition, the N-phenylsulfonyl substituents stretch in the direction of the carbonyl group of central piperidone, giving an overall shape of an “organic clip” [16]. The dihedral angles between N-phenylsulfonyl group and piperidone ring are 38.7(3)° and 27.6(4)°, respectively.

According to the literature, the production of pro-inflammatory cytokines, such as express rate of NO production, TNF-α and IL-6, can indicate the degree of inflammation [8], [17], [18]. In our study, the effect of title compound on NO production in mouse RAW264.7 cells induced by LPS was examined by ELISA. PDTC was used as a reference standard. After treatment with PDTC, the express rate for NO production in RAW264.7 cells was 68.32 ± 2.69%. After treatment with title compound, the express rate of NO production was significantly decreased, reaching 48.29 ± 0.71%. The result showed that title compound displayed potential inhibitory effects on LPS-induced NO secretion compared to PDTC.

Funding source: Shandong Provincial Natural Science Foundation

Award Identifier / Grant number: ZR2019MB032

Funding statement: This work was supported by Shandong Provincial Natural Science Foundation (No. ZR2019MB032), national students innovation and entrepreneurship training program.

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Received: 2019-09-12
Accepted: 2019-10-24
Published Online: 2019-11-09
Published in Print: 2020-02-25

©2019 An-Qi Wang 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. Synthesis and crystal structure of bis{5-fluorine-2-(((4-(1-(methoxy-imino)ethyl)phenyl) imino)methyl)phenolato-κ2N,O}copper(II), C32H28CuF2N4O4
  3. Redetermination of the crystal structure of N′-(3-ethoxy-2-hydroxybenzylidene)-4-fluorobenzohydrazide monohydrate, C16H17FN2O4
  4. The crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl) ethylidene)-2-hydroxybenzohydrazide, C15H12ClFN2O2
  5. Crystal structure of (E)-N-[4-(1H)-imidazolyl phenyl]-(2-methylphenyl)methanimine, C17H15N3
  6. The crystal structure of 1-benzyl-4-(2-(phenylethynyl)phenyl)-1H-1,2,3-triazole, C23H17N3
  7. Crystal structure of catena-poly[{μ2-1,5-bis(diphenylphosphanyl)pentane-κ2P:P′}dichloridocadmium(II)], C29H30CdCl2P2
  8. Crystal structure of methyl (E)-N2-((3-methylquinolin-8-yl)sulfonyl)-Nω′-nitro-L-argininate - ethanol (1/1), C19H28N6O7S
  9. The crystal structure of trans-carbonyl-(diphenylcyclohexyl-phosphine-κP)iodidomethyl-(2-oxopyridin-1(2H)-olato-κ2O,O′)rhodium(III), C25H28INO3PRh
  10. Crystal structure of N-(amino(pyrazin-2-yl)methylene)-6-methylpyridin-1-ium-3-carbohydrazonate-κ3O,N,N′)-(dinitrato-κ1O)zinc(II), C12H12N8O7Zn
  11. The crystal structure of dichlorido-(tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′)chromium(III) chloride — methanol (1/3), CrC27H33Cl3N7O3
  12. Crystal structure of catena-poly[aqua(μ4-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ8O,O′:O′,N:N′,O′′:O′′,O′′′))silver(I)], C10H24Ag2N2O10S2
  13. Crystal structure of bis(μ3-oxido)-bis(μ2–2,3,4,5-tetrafluorobenzoato-κ2O:O′)-bis(2,3,4,5-tetrafluorobenzoato-κO)-oktakis(3-chlorobenzyl-κC)tetratin(IV), C84H52Cl8F16O10Sn4
  14. Crystal structure of (E)-1-{4-[(4-fluoro-2-hydroxybenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15FN2O2
  15. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-N,N′)zinc(II)], {C20H30N4O4P2S4Zn}n
  16. Crystal structure of methyl 2-(4-(3-iodopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C15H12IN3O2
  17. Crystal structure of hexacarbonyl-(μ2-methanoato-k2O:O′)-(μ2–bis(di-p-tolylphosphino)cyclohexylamine-κ2P:P′)dirhenium(I), C42H45NO8P2Re2
  18. The cocrystal structure of 1′-hydroxy-1H,1′H-[5,5′-bitetrazol]-1-olate and 1,10-phenanthrolin-1-ium, C14H10N10O2
  19. The crystal structure of 1-benzyl-2-((4-(tert-butyl)phenyl)ethynyl)pyridin-1-ium bromide,C24H24BrN
  20. Crystal structure of (5,5′-bitetrazole-1,1′-diolate)-bis(1,10-phenanthroline)-copper(II), C26H16CuN12O2
  21. Crystal structure of bis(ammonium) diaqua-tetrakis(4-hydroxybenzoato)-manganese(II) tetrahydrate, [NH4]2[C28H24MnO14] ⋅ 4(H2O)
  22. The crystal structure of 3-chloro-1-hydrazino-2,4,6-trinitrobenzene, C6H4ClN5O6
  23. Crystal structure of catena-[(μ2-pyrazine-κ2N:N′)-bis(O,O′-di-ethyldithiophosphato-κ2S,S′)cadmium(II)], {C12H24CdN2O4P2S4}n
  24. Crystal structure of catena-poly[(μ2-pyrazine-N,N′)-bis(O,O′-di-isopropyldithiophosphato-S,S′)cadmium(II) acetonitrile di-solvate], [C16H32CdN2O4P2S4⋅2(C2H3N)]n
  25. Crystal structure of catena-poly{(μ2-N1,N2-bis[(pyridin-4-yl)methyl]ethanediamide-κ2N:N′)-bis(O,O′-di-isopropyldithiophosphato-κ1S)zinc(II)} — acetonitrile (1/1), C26H42N4O6P2S4Zn⋅C2H3N
  26. Crystal structure of tetraqua-bis(4-(hydroxymethyl)benzoato-κO)cobalt(II), C16H22O10Co
  27. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(4-pyridylmethylene)hydrazine-N,N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  28. Crystal structure of catena-poly[(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)-bis(O,O′-dimethyl dithiophosphato-κ2-S,S′)cadmium(II)], {C16H22CdN4O4P2S4}n
  29. Crystal structure of catena-poly[(bis(O,O′-diethyl dithiophosphato-κ2S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  30. The crystal structure of catena-poly[(E)-2-(((5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)imino)methyl)phenol], C12H15N3OS2Sn
  31. Crystal structure of dichlorido(N-o-tolyl-1,1-di-p-tolylphosphanamine–κ1P)-(methoxydi-p-tolylphosphane-κ1P)palladium(II), C36H39Cl2NOP2Pd
  32. The crystal structure of the triclinic polymorph of hexameric (trimethylsilyl)methyllithium, C24H66Li6Si6
  33. Crystal structure of bis(hydroxydi(pyridin-2-yl)methanolato-κ3N,N′O)cobalt(III) 7,7,8,8-tetracyanoquinodimethane, C34H22CoN8O4
  34. Synthesis and crystal structure of benzyl 5-oxo-5-phenyl-2-(quinolin-2-yl)pentanoate, C27H23NO3
  35. Crystal structure of 5,5-dimethyl-3-oxocyclohex-1-en-1-yl 4-(2,2-dichloroacetyl)-3,4-dihydro-2 H-benzo[b][1,4]oxazine-7-carboxylate, C19H19Cl2NO5
  36. Crystal structure of dipentyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C18H28O6
  37. The crystal structure of catena-poly[diaqua-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)dicadmium(II)], C30H18Cd2N2O10S2
  38. Crystal structure of 2,7-diiodo-1,3,6,8-tetramethyl-bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine, C14H14B2F4I2N4
  39. A dinuclear Eu(III) complex in the crystal structure of dodecaaqua-bis(μ2-4-(1H-tetrazol-5-yl)benzoato-κ2O:O′) bis(5-(4-carboxylatophenyl)tetrazol-1-ide) tetrahydrate, C32H50Eu2N16O24
  40. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one, C24H18F2N2O3S
  41. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-acetamidophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one-methanol-hydrate (2/1/1), C53H50F2N6O10S2
  42. Crystal structure of 4-dimethylamino-pyridin-1-ium uracil-1-acetate, C13H16N4O4
  43. Crystal structure of dimethylammonium 5-fluorouracil-1-acetate, C8H12N3O4F
  44. Crystal structure of bis(N′-((5-(ethoxycarbonyl)-1H-pyrrol-2-yl)methylene)-N-ethylcarbamohydrazonothioato-κ2N,O)nickel(II), C22H30N8O4S2Ni
  45. Crystal structure of chlorido-(η5-pentamethylcyclopentadienyl)-((bis-pyrazol-1-yl)methane-κ2N,N′) rhodium(III) hexafluorophosphate. (C17H23ClN4RhF6P)
  46. The crystal structure of 5-(benzofuran-2-carbonyl)-N-cyclohexyl-5,6-dihydrophenanthridine-6-carboxamide, C29H26N2O3
  47. The crystal structure of 2-oxo-2H-chromen-4-yl acetate, C11H8O4
  48. The crystal structure of 2-nitroisophthalic acid, C8H5NO6
  49. Crystal structure of 3-fluoro-9-methoxy-4b,5,14,15-tetrahydro-6H-isoquinolino [2′,1′:1,6]pyrazino[2,3-b]quinoxaline, C19H17FN4O
  50. Crystal structure of (4-fluorobenzyl-κC)(bis(2-hydroxyethyl) carbamodithioato-κ2S,S′)(2,2′-imino-diethanolato-κ3N,O,O′)tin(IV), C16H25FN2O4S2Sn
  51. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-bromophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18BrF3N2O3S
  52. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18ClF3N2O3S
  53. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridomanganate(II), C10H16Cl4MnN2
  54. The crystal structure of 3-carboxy-5-methylpyridin-1-ium-2-carboxylate, C8H7NO4
  55. Crystal structure of bis(3-methoxy-N-(1-(pyridin-2-yl)ethylidene)benzohydrazonato κ3O,N,N′)zinc(II), C30H28N6O4Zn
  56. Crystal structure of dichlorido-(4,4′-dichloro-2,2′-bipyridine-κ2N,N′)platinum(II) — acetone (1/1), C13H12Cl4N2PtO
  57. Crystal structure of diethyl 6,12-bis(4-fluorophenyl)-2,10-dimethoxy-3,9-diphenyl-3,9-diazatetracyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C42H42F2N2O6
  58. Synthesis and crystal structure of (1E,3E)-2-hydroxy-5-methylisophthalaldehyde O,O-di(2-((((E)-(2-hydroxynaphthalen-1-yl)methylene)amino)oxy)ethyl) dioxime, C35H32N4O7
  59. The crystal structure of 2-phenyl-4,6-bis(prop-2-yn-1-yloxy)-1,3,5-triazine, C15H11N3O2
  60. Crystal structure of 7-(2-{4-[(4-bromophenyl)methyl]piperazin-1-yl}ethoxy)-2H-chromen-2-one, C22H23BrN2O3
  61. Crystal structure of bis-[N-(3-ethyl-1-pyrazin-2-yl-ethylidene)-3-bromo-benzoic acid-hydrazonato-κ3O,N,N′)]-cadmium(II), C30H28N8O2Br2Cd
  62. Crystal structure of 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one, C12H9FO3
  63. Crystal structure of 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid, C14H18O4
  64. The crystal structure of 3-bromo-6-methoxy-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, C13H19BBrNO3
  65. The crystal structure of 6-methyl-3,20-dioxo-19-norpregna-4,6-dien-17-yl acetate–2,4-dihydroxybenzoic acid (1/1), C30H36O8
  66. The crystal structure of (5-chloro-2-hydroxy-N-(4-methoxy-2-oxidobenzylidene)benzohydrazonato-κ3N,O,O′)-(pyridine-κ1N)copper(II), C20H16ClCuN3O4
  67. Crystal structure of (E)-2-cyano-N′-(1-(3-ethylpyrazin-2-yl)ethylidene)acetohydrazide, C11H3N5O
  68. Crystal structure of (2,7-dihexyl-9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane), C51H56OP2
  69. Crystal structure of 5-((bis(pyridin-2-ylmethyl)amino)methyl)quinolin-8-ol, C22H20N4O
  70. Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
  71. The crystal structure of [(tetra-μ2-2,6-difluorobenzoato-κ2O:O′)-bis-(2,6-difluorobenzoato-κ2O:O′)-bis-(1,10-phenanthroline-κ2N:N′)]dierbium(III) C66H34N4O12F12Er2
  72. Crystal structure of bis(3-chloro-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-k3N,N′,O)nickel(II), C26H20N8O2Cl2Ni
  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
https://doi.org/10.1515/ncrs-2019-0686
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Artikel in diesem Heft

  1. Frontmatter
  2. Synthesis and crystal structure of bis{5-fluorine-2-(((4-(1-(methoxy-imino)ethyl)phenyl) imino)methyl)phenolato-κ2N,O}copper(II), C32H28CuF2N4O4
  3. Redetermination of the crystal structure of N′-(3-ethoxy-2-hydroxybenzylidene)-4-fluorobenzohydrazide monohydrate, C16H17FN2O4
  4. The crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl) ethylidene)-2-hydroxybenzohydrazide, C15H12ClFN2O2
  5. Crystal structure of (E)-N-[4-(1H)-imidazolyl phenyl]-(2-methylphenyl)methanimine, C17H15N3
  6. The crystal structure of 1-benzyl-4-(2-(phenylethynyl)phenyl)-1H-1,2,3-triazole, C23H17N3
  7. Crystal structure of catena-poly[{μ2-1,5-bis(diphenylphosphanyl)pentane-κ2P:P′}dichloridocadmium(II)], C29H30CdCl2P2
  8. Crystal structure of methyl (E)-N2-((3-methylquinolin-8-yl)sulfonyl)-Nω′-nitro-L-argininate - ethanol (1/1), C19H28N6O7S
  9. The crystal structure of trans-carbonyl-(diphenylcyclohexyl-phosphine-κP)iodidomethyl-(2-oxopyridin-1(2H)-olato-κ2O,O′)rhodium(III), C25H28INO3PRh
  10. Crystal structure of N-(amino(pyrazin-2-yl)methylene)-6-methylpyridin-1-ium-3-carbohydrazonate-κ3O,N,N′)-(dinitrato-κ1O)zinc(II), C12H12N8O7Zn
  11. The crystal structure of dichlorido-(tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′)chromium(III) chloride — methanol (1/3), CrC27H33Cl3N7O3
  12. Crystal structure of catena-poly[aqua(μ4-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ8O,O′:O′,N:N′,O′′:O′′,O′′′))silver(I)], C10H24Ag2N2O10S2
  13. Crystal structure of bis(μ3-oxido)-bis(μ2–2,3,4,5-tetrafluorobenzoato-κ2O:O′)-bis(2,3,4,5-tetrafluorobenzoato-κO)-oktakis(3-chlorobenzyl-κC)tetratin(IV), C84H52Cl8F16O10Sn4
  14. Crystal structure of (E)-1-{4-[(4-fluoro-2-hydroxybenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15FN2O2
  15. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-N,N′)zinc(II)], {C20H30N4O4P2S4Zn}n
  16. Crystal structure of methyl 2-(4-(3-iodopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C15H12IN3O2
  17. Crystal structure of hexacarbonyl-(μ2-methanoato-k2O:O′)-(μ2–bis(di-p-tolylphosphino)cyclohexylamine-κ2P:P′)dirhenium(I), C42H45NO8P2Re2
  18. The cocrystal structure of 1′-hydroxy-1H,1′H-[5,5′-bitetrazol]-1-olate and 1,10-phenanthrolin-1-ium, C14H10N10O2
  19. The crystal structure of 1-benzyl-2-((4-(tert-butyl)phenyl)ethynyl)pyridin-1-ium bromide,C24H24BrN
  20. Crystal structure of (5,5′-bitetrazole-1,1′-diolate)-bis(1,10-phenanthroline)-copper(II), C26H16CuN12O2
  21. Crystal structure of bis(ammonium) diaqua-tetrakis(4-hydroxybenzoato)-manganese(II) tetrahydrate, [NH4]2[C28H24MnO14] ⋅ 4(H2O)
  22. The crystal structure of 3-chloro-1-hydrazino-2,4,6-trinitrobenzene, C6H4ClN5O6
  23. Crystal structure of catena-[(μ2-pyrazine-κ2N:N′)-bis(O,O′-di-ethyldithiophosphato-κ2S,S′)cadmium(II)], {C12H24CdN2O4P2S4}n
  24. Crystal structure of catena-poly[(μ2-pyrazine-N,N′)-bis(O,O′-di-isopropyldithiophosphato-S,S′)cadmium(II) acetonitrile di-solvate], [C16H32CdN2O4P2S4⋅2(C2H3N)]n
  25. Crystal structure of catena-poly{(μ2-N1,N2-bis[(pyridin-4-yl)methyl]ethanediamide-κ2N:N′)-bis(O,O′-di-isopropyldithiophosphato-κ1S)zinc(II)} — acetonitrile (1/1), C26H42N4O6P2S4Zn⋅C2H3N
  26. Crystal structure of tetraqua-bis(4-(hydroxymethyl)benzoato-κO)cobalt(II), C16H22O10Co
  27. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(4-pyridylmethylene)hydrazine-N,N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  28. Crystal structure of catena-poly[(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)-bis(O,O′-dimethyl dithiophosphato-κ2-S,S′)cadmium(II)], {C16H22CdN4O4P2S4}n
  29. Crystal structure of catena-poly[(bis(O,O′-diethyl dithiophosphato-κ2S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  30. The crystal structure of catena-poly[(E)-2-(((5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)imino)methyl)phenol], C12H15N3OS2Sn
  31. Crystal structure of dichlorido(N-o-tolyl-1,1-di-p-tolylphosphanamine–κ1P)-(methoxydi-p-tolylphosphane-κ1P)palladium(II), C36H39Cl2NOP2Pd
  32. The crystal structure of the triclinic polymorph of hexameric (trimethylsilyl)methyllithium, C24H66Li6Si6
  33. Crystal structure of bis(hydroxydi(pyridin-2-yl)methanolato-κ3N,N′O)cobalt(III) 7,7,8,8-tetracyanoquinodimethane, C34H22CoN8O4
  34. Synthesis and crystal structure of benzyl 5-oxo-5-phenyl-2-(quinolin-2-yl)pentanoate, C27H23NO3
  35. Crystal structure of 5,5-dimethyl-3-oxocyclohex-1-en-1-yl 4-(2,2-dichloroacetyl)-3,4-dihydro-2 H-benzo[b][1,4]oxazine-7-carboxylate, C19H19Cl2NO5
  36. Crystal structure of dipentyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C18H28O6
  37. The crystal structure of catena-poly[diaqua-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)dicadmium(II)], C30H18Cd2N2O10S2
  38. Crystal structure of 2,7-diiodo-1,3,6,8-tetramethyl-bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine, C14H14B2F4I2N4
  39. A dinuclear Eu(III) complex in the crystal structure of dodecaaqua-bis(μ2-4-(1H-tetrazol-5-yl)benzoato-κ2O:O′) bis(5-(4-carboxylatophenyl)tetrazol-1-ide) tetrahydrate, C32H50Eu2N16O24
  40. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one, C24H18F2N2O3S
  41. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-acetamidophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one-methanol-hydrate (2/1/1), C53H50F2N6O10S2
  42. Crystal structure of 4-dimethylamino-pyridin-1-ium uracil-1-acetate, C13H16N4O4
  43. Crystal structure of dimethylammonium 5-fluorouracil-1-acetate, C8H12N3O4F
  44. Crystal structure of bis(N′-((5-(ethoxycarbonyl)-1H-pyrrol-2-yl)methylene)-N-ethylcarbamohydrazonothioato-κ2N,O)nickel(II), C22H30N8O4S2Ni
  45. Crystal structure of chlorido-(η5-pentamethylcyclopentadienyl)-((bis-pyrazol-1-yl)methane-κ2N,N′) rhodium(III) hexafluorophosphate. (C17H23ClN4RhF6P)
  46. The crystal structure of 5-(benzofuran-2-carbonyl)-N-cyclohexyl-5,6-dihydrophenanthridine-6-carboxamide, C29H26N2O3
  47. The crystal structure of 2-oxo-2H-chromen-4-yl acetate, C11H8O4
  48. The crystal structure of 2-nitroisophthalic acid, C8H5NO6
  49. Crystal structure of 3-fluoro-9-methoxy-4b,5,14,15-tetrahydro-6H-isoquinolino [2′,1′:1,6]pyrazino[2,3-b]quinoxaline, C19H17FN4O
  50. Crystal structure of (4-fluorobenzyl-κC)(bis(2-hydroxyethyl) carbamodithioato-κ2S,S′)(2,2′-imino-diethanolato-κ3N,O,O′)tin(IV), C16H25FN2O4S2Sn
  51. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-bromophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18BrF3N2O3S
  52. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18ClF3N2O3S
  53. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridomanganate(II), C10H16Cl4MnN2
  54. The crystal structure of 3-carboxy-5-methylpyridin-1-ium-2-carboxylate, C8H7NO4
  55. Crystal structure of bis(3-methoxy-N-(1-(pyridin-2-yl)ethylidene)benzohydrazonato κ3O,N,N′)zinc(II), C30H28N6O4Zn
  56. Crystal structure of dichlorido-(4,4′-dichloro-2,2′-bipyridine-κ2N,N′)platinum(II) — acetone (1/1), C13H12Cl4N2PtO
  57. Crystal structure of diethyl 6,12-bis(4-fluorophenyl)-2,10-dimethoxy-3,9-diphenyl-3,9-diazatetracyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C42H42F2N2O6
  58. Synthesis and crystal structure of (1E,3E)-2-hydroxy-5-methylisophthalaldehyde O,O-di(2-((((E)-(2-hydroxynaphthalen-1-yl)methylene)amino)oxy)ethyl) dioxime, C35H32N4O7
  59. The crystal structure of 2-phenyl-4,6-bis(prop-2-yn-1-yloxy)-1,3,5-triazine, C15H11N3O2
  60. Crystal structure of 7-(2-{4-[(4-bromophenyl)methyl]piperazin-1-yl}ethoxy)-2H-chromen-2-one, C22H23BrN2O3
  61. Crystal structure of bis-[N-(3-ethyl-1-pyrazin-2-yl-ethylidene)-3-bromo-benzoic acid-hydrazonato-κ3O,N,N′)]-cadmium(II), C30H28N8O2Br2Cd
  62. Crystal structure of 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one, C12H9FO3
  63. Crystal structure of 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid, C14H18O4
  64. The crystal structure of 3-bromo-6-methoxy-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, C13H19BBrNO3
  65. The crystal structure of 6-methyl-3,20-dioxo-19-norpregna-4,6-dien-17-yl acetate–2,4-dihydroxybenzoic acid (1/1), C30H36O8
  66. The crystal structure of (5-chloro-2-hydroxy-N-(4-methoxy-2-oxidobenzylidene)benzohydrazonato-κ3N,O,O′)-(pyridine-κ1N)copper(II), C20H16ClCuN3O4
  67. Crystal structure of (E)-2-cyano-N′-(1-(3-ethylpyrazin-2-yl)ethylidene)acetohydrazide, C11H3N5O
  68. Crystal structure of (2,7-dihexyl-9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane), C51H56OP2
  69. Crystal structure of 5-((bis(pyridin-2-ylmethyl)amino)methyl)quinolin-8-ol, C22H20N4O
  70. Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
  71. The crystal structure of [(tetra-μ2-2,6-difluorobenzoato-κ2O:O′)-bis-(2,6-difluorobenzoato-κ2O:O′)-bis-(1,10-phenanthroline-κ2N:N′)]dierbium(III) C66H34N4O12F12Er2
  72. Crystal structure of bis(3-chloro-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-k3N,N′,O)nickel(II), C26H20N8O2Cl2Ni
  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
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Heruntergeladen am 17.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2019-0686/html
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