Home 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
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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

  • Yan-Qiu Zhou , Gui-Ge Hou ORCID logo , Qing-Guo Meng and Yun Hou ORCID logo EMAIL logo
Published/Copyright: December 20, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 2

Abstract

C25H18ClF3N2O3S, monoclinic, P21/n (no. 14), a = 9.9087(5) Å, b = 21.7843(10) Å, c = 10.2512(6) Å, β = 94.749(5)°, V = 2205.2(2) Å3, Z = 4, Rgt(F) = 0.0448, wRref(F2) = 0.1028, T = 100 K.

CCDC no.: 1868651

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:0.14 × 0.12 × 0.11 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.33 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:29.6°, >99%
N(hkl)measured, N(hkl)unique, Rint:19019, 5362, 0.040
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4204
N(param)refined:316
Programs:CrysAlisPRO [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
C10.36719(19)0.01360(9)0.7383(2)0.0243(4)
H1A0.413494−0.0255560.7484110.029*
H1B0.2706010.0057360.7346390.029*
C20.40727(18)0.05309(8)0.8558(2)0.0223(4)
C30.50729(18)0.10386(8)0.8421(2)0.0221(4)
C40.57578(18)0.10822(8)0.71815(19)0.0209(4)
C50.54113(18)0.06107(9)0.6148(2)0.0240(4)
H5A0.5567070.0779510.5297630.029*
H5B0.5997240.0256810.6300950.029*
C60.36069(18)0.04677(9)0.9741(2)0.0232(4)
H60.3977970.0739651.0371880.028*
C70.26083(18)0.00403(9)1.0204(2)0.0244(4)
C80.2181(2)−0.05078(9)0.9602(2)0.0283(4)
H80.256554−0.0643710.8856030.034*
C90.1176(2)−0.08473(10)1.0129(2)0.0316(5)
H90.088942−0.1206780.9701640.038*
C100.1033(2)−0.01748(10)1.1811(2)0.0321(5)
H100.065378−0.0059621.2573980.039*
C110.2019(2)0.01939(9)1.1356(2)0.0277(4)
H110.2294480.0546571.1815230.033*
C120.66212(18)0.15485(9)0.7062(2)0.0228(4)
H120.6694780.1833500.7739870.027*
C130.74629(18)0.16552(9)0.59708(19)0.0229(4)
C140.77123(18)0.22534(9)0.5521(2)0.0238(4)
C150.85715(19)0.23483(10)0.4541(2)0.0284(5)
H150.8732370.2744880.4256130.034*
C160.91924(19)0.18544(10)0.3985(2)0.0318(5)
H160.9774370.1919460.3332050.038*
C170.89461(19)0.12670(10)0.4401(2)0.0303(5)
H170.9349480.0934820.4016860.036*
C180.80987(18)0.11691(9)0.5392(2)0.0257(4)
H180.7952920.0770730.5674370.031*
C190.69965(19)0.27899(9)0.6051(2)0.0271(4)
C200.23114(18)0.14497(8)0.59438(19)0.0211(4)
C210.27440(18)0.20120(9)0.54837(19)0.0220(4)
H210.3363830.2027400.4851080.026*
C220.22374(18)0.25479(9)0.5982(2)0.0244(4)
H220.2506780.2927870.5681480.029*
C230.13269(18)0.25123(9)0.6932(2)0.0229(4)
C240.09139(19)0.19570(9)0.7407(2)0.0254(4)
H240.0309970.1943710.8054450.030*
C250.14094(18)0.14205(9)0.6909(2)0.0246(4)
H250.1140260.1042130.7217500.029*
Cl10.06547(5)0.31803(2)0.75425(5)0.03149(14)
F10.73106(12)0.28836(6)0.73354(12)0.0363(3)
F20.56353(11)0.27187(5)0.59193(13)0.0320(3)
F30.72490(13)0.33172(5)0.54540(13)0.0385(3)
N10.39938(15)0.04171(7)0.61467(16)0.0228(3)
N20.05926(17)−0.06926(8)1.12081(19)0.0342(4)
O10.53350(14)0.14026(6)0.93125(14)0.0284(3)
O20.16749(14)0.03602(6)0.51482(15)0.0321(4)
O30.34327(14)0.09227(6)0.40400(14)0.0299(3)
S10.28177(5)0.07630(2)0.52095(5)0.02351(12)

Source of material

2-(Trifluoromethy)benzaldehyde (1.74 g, 10.0 mmol), 4-pyridinecarboxaldehyde (1.07 g, 10.0 mmol) and 4-piperidone hydrate hydrochloride (1.35 g, 10.0 mmol) were dissolved in dilute acetic acid (25 mL). This mixture was passed through by dry HCL gas 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 precipitates were added into 100 mL water, and then aqueous Na2CO3 solution was added until the pH value was adjusted to about 7. The precipitates were filtered, subsequently washed by water, and purified on silica gel by column using methanol/petroleum ether/EtOAc (1:10:10, v/v/v) as the eluent to afford a yellow intermediate. Next, the intermediate (0.69 g, 2.0 mmol), and 4-chlorobenzenesulfonyl chloride (0.46 g, 2.2 mmol) were dissolved in dichloromethane (50 mL). Two drops of pyridine were added. 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 get light yellow crystals of the 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 as a reference standard. When the concentration of the title compound was 6.0 μM, it had no significant toxicity on experimental RAW264.7 cells. Firstly, RAW264.7 cells were pretreated for 2.0 h with 30 μM of PDTC or 6.0 μM of title compound, respectively. Secondly, the cells were treated with LPS (1.0 μg/mL) for 22 h, and then 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, USA). The experiment was carried out in triplicate.

Experimental details

The 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

Because of low bioactivities, poor aqueous solubility and false positive problem of curcumin, it is rarely used in clinical practice [4]. In order to improve these aspects of the problem, lots of curcumin analogues were synthesized through structural modification, such as (3E,5E)-3,5-bis(arylidene)-4-piperidone derivatives (BAPs). In this class of compounds, two α,β-unsaturated keto groups cause greater predilection or sequential interaction for bio-thiols in tumors rather than normal cells [5], [6]. In our group, some BAPs with better antitumor and anti-inflammatory properties were reported [7], [8], [9]. They involve some strong electron-withdrawing substituent groups (Such as -NO2, -CN, -CF3) and great electron-donating substitutes (Such as -NHAc, -OMe, -CMe3) resulting in improving antitumor and anti-inflammatory activity to different extent [10], [11], [12].

Changing one side of BAPs to 4-pyridine substituents, while on the other side of BAPs a 2-CF3 group is added, asymmetric BAPs could be generated [8]. Our interests lie in incorporation of different substituent groups on the end of N-phenylsulfonyl substituent, and find the desired and improved antitumor and anti-inflammatory activities in contrast to symmetric derivatives.

Single-crystal structure analysis reveals that the title structure contains one drug molecule in the asymmetric unit (cf. the figure 1). Bond lengths and angles are all in the expected ranges. The central 3,5-bis(arylidene)-4-piperidone expand both sides in a linear fashion, and pyridyl and arylidene on both sides of central piperidone adopt the E stereochemistry [13], [14]. The dihedral angle between the mean planes of the pyridyl and central piperidone is 11.9(2)°, while the dihedral angle between the mean planes of the arylidene and central piperidone is 45.7(3)°. In addition, the N-phenylsulfonyl substituents are going to stretch in the direction of the carbonyl group of central piperidone. It looks like an “organic clip” [15]. The dihedral angle between N-phenylsulfonyl group and piperidone ring is 42.6(3)°.

In our study, the effect of title compound on pro-inflammatory cytokine (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 expression rate for NO production in RAW264.7 cells was 68.32 ± 2.69%. For title compound, the expression rate of NO production could reach 52.19 ± 0.37%. The result showed that title compound displayed potential inhibitory effect on LPS-induced NO secretion than PDTC [8], [16], [17].

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 81601049

Funding source: Shandong Provincial Natural Science Foundation

Award Identifier / Grant number: ZR2019MB032

Funding statement: This work was supported by the National Natural Science Foundation of China (no. 81601049) and Shandong Provincial Natural Science Foundation (No. ZR2019MB032).

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Received: 2019-09-21
Accepted: 2019-12-05
Published Online: 2019-12-20
Published in Print: 2020-02-25

©2019 Yan-Qiu Zhou et al., published by De Gruyter, Berlin/Boston

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

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  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-2019-0716
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Articles in the same Issue

  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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