Home Physical Sciences Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3,5-bis(4-fluorobenzylidene)piperidin-4-one-dichloromethane (1/1), C26H20Cl3F2NO3S
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Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3,5-bis(4-fluorobenzylidene)piperidin-4-one-dichloromethane (1/1), C26H20Cl3F2NO3S

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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 4

Abstract

C26H20Cl3F2NO3S, triclinic, P1̄ (no. 2), a = 8.6281(7) Å, b = 11.3695(9) Å, c = 14.3529(11) Å, α = 68.166(7)°, β = 80.707(7)°, γ = 71.169(7)°, V = 1235.65(19) Å3, Z = 2, Rgt(F) = 0.0564, wRref(F2) = 0.1376, T = 100.00(10) K.

CCDC no.: 1995026

The molecular structure is shown in the figure (The solvent molecule is not shown for clarity). 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:0.13 × 0.12 × 0.11 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.50 mm−1
Diffractometer, scan mode:SuperNova, φ and ω scans
θmax, completeness:25.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:9047, 4615, 0.032
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3604
N(param)refined:335
Programs:CrysAlisPRO [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
C10.1505(4)0.1361(3)0.5557(2)0.0240(7)
H1A0.1231570.1966820.5928110.029*
H1B0.1752920.0468030.6039750.029*
C20.0032(4)0.1610(3)0.4983(2)0.0229(7)
C30.0335(4)0.1375(3)0.4005(2)0.0243(7)
C40.2068(4)0.0958(3)0.3617(2)0.0217(7)
C50.3424(4)0.0674(3)0.4285(2)0.0232(7)
H5A0.367902−0.0244210.4721550.028*
H5B0.4401410.0809070.3871110.028*
C6−0.1521(4)0.2080(3)0.5283(2)0.0235(7)
H6−0.2316990.2226790.4853950.028*
C7−0.2125(4)0.2393(3)0.6203(2)0.0245(7)
C8−0.3574(4)0.3413(3)0.6180(3)0.0297(8)
H8−0.4140990.3854850.5591510.036*
C9−0.4179(4)0.3776(3)0.7017(3)0.0336(8)
H9−0.5126240.4469960.6993700.040*
C10−0.3343(5)0.3085(4)0.7882(3)0.0333(8)
C11−0.1940(4)0.2040(3)0.7957(3)0.0303(8)
H11−0.1418060.1575850.8560740.036*
C12−0.1334(4)0.1703(3)0.7113(2)0.0263(7)
H12−0.0385020.1007380.7147070.032*
C130.2336(4)0.0919(3)0.2682(2)0.0246(7)
H130.1403810.1190170.2321390.029*
C140.3899(4)0.0507(3)0.2150(2)0.0253(7)
C150.5229(4)−0.0547(3)0.2621(3)0.0273(8)
H150.514740−0.1003260.3306700.033*
C160.6664(4)−0.0915(4)0.2073(3)0.0331(8)
H160.753911−0.1620640.2385260.040*
C170.6774(5)−0.0227(4)0.1069(3)0.0413(10)
C180.5488(5)0.0814(4)0.0573(3)0.0468(11)
H180.5588890.127080−0.0111220.056*
C190.4056(5)0.1155(4)0.1121(3)0.0390(9)
H190.3172120.1835430.0793870.047*
C200.1837(4)0.3993(3)0.3456(2)0.0213(7)
C210.0247(4)0.4625(3)0.3716(2)0.0223(7)
H21−0.0052980.4576570.4378880.027*
C22−0.0882(4)0.5325(3)0.2977(3)0.0277(8)
H22−0.1953180.5747560.3137440.033*
C23−0.0402(4)0.5387(3)0.2005(3)0.0297(8)
C240.1183(4)0.4793(3)0.1732(3)0.0302(8)
H240.1483730.4869520.1064880.036*
C250.2309(4)0.4087(3)0.2465(2)0.0255(7)
H250.3380950.3674730.2297460.031*
C260.7406(5)0.2420(4)0.1571(3)0.0588(13)
H26A0.7772470.2585990.2101900.071*
H26B0.6848850.1740140.1880040.071*
Cl1−0.18620(13)0.62225(12)0.10932(8)0.0556(3)
Cl30.91159(12)0.18618(13)0.08250(8)0.0555(3)
F1−0.3932(3)0.3428(2)0.87104(16)0.0446(6)
F20.8169(3)−0.0589(2)0.05308(19)0.0606(7)
N10.2965(3)0.1528(2)0.48993(19)0.0214(6)
O1−0.0804(3)0.1524(2)0.35244(17)0.0311(6)
O20.2820(3)0.3543(2)0.52082(16)0.0286(5)
O30.4865(3)0.2816(2)0.39536(17)0.0291(5)
S10.32409(10)0.30046(8)0.44126(6)0.0220(2)
Cl2a0.5987(3)0.39303(19)0.0811(2)0.0402(8)
Cl2’b0.6653(13)0.3959(3)0.1206(6)0.072(3)

  1. aOccupancy: 0.642(11), bOccupancy: 0.358(11).

Source of material

For the synthesis, 4-piperidone hydrochloride (0.68 g, 0.005 mol) and 4-fluorobenzaldehyde (1.24 g, 0.01 mol) were dissolved in 10 mL acetic acid in a 25 mL beaker. After continuous injection of dried HCl gas for 45 min, the mixture was stirred for 8 h at ambient temperature, and the reaction endpoint was determined by thin layer chromatography (TLC). After the reaction has been completed, the precipitate was extracted and dissolved in water. Then the dilute sodium hydroxide solution was used to adjust the pH value to neutral. The precipitate was recrystallized with 70% methanol solution to obtain the intermediate BAP-H, which was directly used in the following reaction. The intermediates BAP-H and 4-chlorobenzenesulfonyl chloride (1.05 g, 0.005 mol) were dissolved in 100 mL dichloromethane. After addition of three drops of pyridine, the mixture was stirred overnight at ambient temperature, and the reaction endpoint was determined by TLC. The reaction solution was washed twice with 2 mol/L hydrochloric acid solution lotion, dried with anhydrous sodium sulfate, concentrated under reduced pressure and we obtained yellow solid. The yellow solid was recrystallized from dichloromethane/methanol (1:1, v/v) to give yellow crystal.

Process of anti-inflammatory activity test: Anti-inflammatory activity was evaluated by ELISA assay to detect changes in cytokine NO secretion in the inflammatory model of RAW264.7 cells induced by LPS. Preliminary experiments showed that the target compound had no significant toxicity to RAW264.7 cells at 6.0 μM. The logarithmic RAW264.7 cells were collected and were cultured in the incubator for 12 h before dosing. After dosing for 2 h, LPS (1 μg/mL) was added, and 6 parallel double holes were added for each group. After 24 h of treatment, cell supernatants in 96-well plates were taken and the secretion of NO cytokines was detected by ELISA with an ELISA kit (eBioScience, San Diego, CA). Pyrrolidine dithiocarbamate (PDTC) was used as a positive control.

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). Displacement ellipsoids are drawn at the 50% probability level.

Comment

Curcumin is a kind of yellow phenolic pigment, mainly found in the rhizome of turmeric. Because of its anti-inflammatory, anti-bacterial, anti-tumor, anti-rheumatism, anti-alzheimer’s disease and other multiple effects [4], it is highly valued by the medical community at home and abroad. However, its poor water solubility, instability and low bioavailability limit its clinical application [5]. Therefore, in order to improve these disadvantages of it, curcumin was modified to (3E,5E)-3,5-bis(arylidene)-4-piperidone (BAPs). As an curcumin analogues, the main pharmacophores of BAPs contain two α,β-unsaturated ketones. They show selective affinity for sulfhydryl groups in tumor cells, while weak affinity for amino, hydroxyl and other active groups in nucleic acid, with potential specific cytotoxic anti-tumor activity [6], [7], [8], [9]. Recent studies have shown that these compounds have significant anti-tumor and anti-inflammatory activities. Our interests lie in incorporation of different substituent groups on the end of N-phenylsulfonyl substituent, and find the desired and improved anti-inflammatory activities [10], [11], [12]. In this paper, the title compound, (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3,5-bis(4-fluorobenzylidene)piperidin-4-one, was obtained by Claisen-Schmidt condensation reaction and N-benzene sulfonylization reaction, and its anti-inflammatory activity was studied.

Single-crystal structure analysis reveals that the title compound contains one drug molecule and a dichloromethane in the asymmetric unit. Bond lengths and angles are all in the expected ranges. In the solid state, 4-fluorobenzylidene groups on both sides of central piperidone adopt the E stereochemistry of the olefinic double bonds [13]. The dihedral angles between 4-fluorobenzylidenes and central piperidone ring are 33.8(3)° and 44.1(4)°, respectively. In addition, the N-phenylsulfonyl group extends in the same direction as the carbonyl group of the central piperidone moiety, which looks like an “organic clip” [14]. The dihedral angles between the 4-chlorobenzenesulfonyl group and the central piperidone is 23.6(2)°.

In this study, the effect of title compound on pro-inflammatory cytokine (NO) production in mouse RAW264.7 cells induced by LPS was examined by ELISA [15]. Pyrrolidine dithiocarbamate (PDTC) was used as a positive control. After treatment with PDTC for RAW264.7 cells, the expression rate for NO production in RAW264.7 cells was 66.42 ± 1.83%. For title compound, the expression rate of NO production could reach 51.09 ± 1.32%. The result showed that the title compound displayed potential inhibitory effect on LPS-induced NO secretion than PDTC.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (no. 81601049).

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Received: 2020-02-12
Accepted: 2020-04-06
Published Online: 2020-04-25
Published in Print: 2020-06-25

©2020 Li-Xia Zhang 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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  50. Crystal structure of dichloro-bis-(1-butyl-1H-benzo[d]imidazole)-nickel(II), C22H28Cl2N4Ni
  51. The crystal structure of 2-(2,3-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one, C17H14O5
  52. The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C30H25FN10S⋅C3H7NO
  53. The crystal structure of 1,8-bis(pyridin-4-ylethynyl)anthracene-1,2,4,5-tetrafluoro-3,6-diiodobenzene (2/1), C62H32F4I2N4
  54. The crystal structure of 3,6-di-tert-butyl-1,8-diiodo-9-methyl-9H-carbazole, C21H25I2N
  55. The crystal structure of 8-((4-chlorophenylamino)methylene)-6,10-dioxaspiro[4.5]decane-7,9-dione, C15H14ClNO4
  56. The crystal structure of catena-poly[oktaaqua-bis(μ2-4,4′-ethene-1,2-diyldipyridine-κ2N:N′)-(μ2-3,3′-(1-oxidodiazene-1,2-diyl)diphthalato-κ2O:O′)dicobalt(II)] dihydrate, C28H36N4O19Co2
  57. Crystal structure of (E)-1-(2-cyano-3-oxo-1-phenylprop-1-en-1-yl)-3,7-diphenylindolizine-6-carbonitrile, C31H19N3O
  58. Crystal structure of 1,1′-bis(diphenylphosphino)ferrocene-(1,1′-bis(diphenylphosphino)ferrocene-κ2P,P′)-(O-isobutyl sulfurodithioito-κ2S,S′)copper(I), C39H37CuFeOP2S2
  59. Crystal structure of poly[(5-bimethylamino-1-naphthalenesulfonato-κO)-(μ3-hexamethylenetetramino-κ3N:N′:N′′)silver(I)] dihydrate, C36H52Ag2N10O8S2
  60. Crystal structure of poly[μ2-diaqua-(μ2-2-amino-4,5-dicyano-κ2N:N′-imidazol-1-ide)sodium(I)], C5H6N5O2Na
  61. Crystal structure of (1,3-propanediamine-κ2N,N′)(N-(3-aminopropyl)-α-methyl aspartato-κ4N,N′,O,O′)cobalt(III) chloride, C11H24ClCoN4O4
  62. Crystal structure and anti-inflammatory activity of (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one-dichloromethane (1/1), C26H20Cl2F3NO3S
  63. Crystal structure of (S)-(+)-1-cyclohexylethylaminium chloride, C8H18NCl
  64. The crystal structure of tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(o-pyridyl)imidazoline-1-oxyl 3-oxide-κ2N,O)yttrium(III), C24H32N9O13Y
  65. Hydrogen bonding versus packing effects in the crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetraiodidozincate(II), C10H16I4ZnN2
  66. Dimerization of 2-[(2-((2-aminophenyl)thio)phenyl)amino]-cyclohepta-2,4,6-trien-1-one through hydrogen bonding, C19H16N2OS
  67. Crystal structure of 1-(4-chloro-phenyl)-7-ethoxyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C18H12ClF2NO4
  68. Crystal structure of 7-ethoxy-6,8-difluoro-4-oxo-1-pyridin-2-ylmethyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H14F2N2O4
  69. Crystal structure of octahydro-7aR,8′R-dimethylspiro[isobenzofuran-4(1H), 4′ (3′H)-[1H-7,9a]methanocyclohepta[c]pyran]-1′,3, 9′ (3aH,4′aH)-trione, C20H26O5
  70. Crystal structure of bis(5-ethoxy-2-(((1-hydroxy-2-methyl-3-oxidopropan-2-yl)imino)methyl)phenolato-κ3N,O,O’)manganese(IV) – methanol (1/1), C27H38MnN2O9
  71. Crystal structure of 8a,8a′′-oxybis(8aH-8,9-dioxa-3a1λ4-aza-8aλ4-borabenzo[fg]tetracene), C34H22B2N2O5
  72. Crystal structure of bromido-triphenyl-(triphenylarsine oxide-κO)tin(IV), C36H30AsBrOSn
  73. Crystal structure of catena-poly[chlorido-(μ2-formato-κ2O:O′)-(1,10-phenathroline-κ2N,N′)copper(II)], C26H18Cl2Cu2N4O4
  74. The crystal structure of poly[(μ10-5-carboxyisophthalato-κ10O)disodium], C9H4Na2O6
  75. The crystal structure of 3,5-difluoroisonicotinic acid, C6H3F2NO2
  76. The crystal structure of ethyl-1-(N-(adamantan-1-yl)-carbamothioyl)piperidine-4-carboxylate, C19H30N2O2S
  77. Crystal structure of 5-methyl-3-phenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C19H21NO2S
  78. Crystal structure of bis((3-chlorosalicylidene)-ethylenediaminato-κ4N,N′,O,O′)nickel (II), C16H12Cl2NiN2O2
  79. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-4-hydroxybenzohydrazide — dihydrofuran-2(3H)-one (1/1), C18H17ClN2O5
  80. Crystal structure of bis((3-bromosalicylidene)-ethylenediaminato-κ4N,N′,O,O′) nickel (II), C16H12Br2NiN2O2
  81. Crystal structure of trimethylsulfoxonium tetrachloridocobaltate(II) [(CH3)3SO]2CoCl4
https://doi.org/10.1515/ncrs-2020-0085
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of bis [1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O]cobalt(II), C24H22N8O4S2Co
  3. The crystal structure of 1,3-bis(4-(methoxycarbonyl)benzyl)-2-methyl-1H-benzo[d]imidazol-3-ium bromide, C26H25BrN2O4
  4. Crystal structure of {tris((1H-benzo[d]imidazol-2-yl)methyl)amine-κ4N,N′,N′′,N′′′}-(nitrito-κ2O,O′)nickel(II) perchlorate – ethanol (1/1), C26H27ClN8NiO7
  5. Crystal structure of catena-poly[aqua[(μ2-4,5-dicarboxylato-2-(2-carboxylatophenyl)imidazol-1-ido-κ4N,O,O′:N′)](μ2-4,4′-bipyridine-κ2N:N′)dicopper(II)], C22H14Cu2N4O7
  6. Crystal structure of chlorido-tris(4-methylbenzyl-κC)-(triphenylarsine oxide-κO)tin(IV), C42H42AsClOSn
  7. The crystal structure of 4,4′-bipyridinium bis(3-carboxy-2-nitrobenzoate) tetrahydrate, C13H13N2O8
  8. Crystal structure of 1-(3-chlorophenyl)-4-(4-(((2,3-dihydro-1H-inden-5-yl)oxy)methyl)phenethyl)piperazine, C28H31ClN2O
  9. Crystal structure of catena-poly[diaqua-bis(μ2-5,5′-(1H-imidazole-4,5-diyl)bis(tetrazol-2-ido)-κ4N,N′:N′′,N′′′)magnesium], C10H8N20O2Mg
  10. The crystal structure of (E)-2-((2-hydroxy-4-ethoxybenzylidene)amino)-2-methylpropane-1,3-diol monohydrate, C13H21NO5
  11. Crystal structure of catena-poly[diaqua-(μ2-bipyridine-κ2N:N′)-bis(3,5-dichloroisonicotinato-κO)cadmium(II)] dihydrate, C22H20CdCl4N4O8
  12. The crystal structure of 4-(4-chlorophenyl)cyclohexane-1-carboxylic acid, C13H15ClO2
  13. Redetermination of the crystal structure of yttrium(III) trinitrate(V) pentahydrate, Y(NO3)3 ⋅ 5 H2O, H10N3O14Y
  14. Crystal structure of catena-poly[di-μ2-chlorido-1,10-phenanthroline-κ2N,N′-cadmium(II)], C12H8Cl2CdN2
  15. Crystal structure of 4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)oxy)benzoic acid, C13H9F3N2O3
  16. Crystal structure of 3-acetyl-4-hydroxybenzoic acid, C18H16O8
  17. Crystal structure of bis(N,2-bis(4-ethoxybenzylidene)hydrazine-1-carbohydrazonothioato-κ2N,S)nickel(II) — N,N-dimethylformamide (1/2), C44H56N10S2O6Ni
  18. The crystal structure of 5-chloro-4,6-dimethoxypyrimidin-2-amine, C6H8ClN3O2
  19. Crystal structure of poly[aqua-(μ4-benzene-1,2,4,5-tetracarboxylato-κ4O,O′,O′′,O′′′)bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N)dinickel(II)], NiC17H14N5O5
  20. Crystal structure of poly[aqua(5-dimethylamino)naphthalene-1-sulfonato-κ2N:O)(μ2-4,4′-bipyridyl -κ2N:N′)silver(I)], C44H44Ag2N6O8S2
  21. Crystal structure of 1-[3-(trifluoromethyl)cinnamoyl]-3-(pyridin-2-yl-κN)pyrazole-κ2N-bis(2-phenylpyridinato-k2C,N)iridium(III) hexafluorophosphate complex, [C40H28F3IrN5O]PF6
  22. Crystal structure of catena-poly[aqua(μ6-piperazine-1,4-bisethanesulfonato-κ6N:N′:O:O′:O′′:O′′′)(μ2-pyrazinyl-κ2N:N′)disilver(I)sesquihydrate], C12H30Ag2N4O11S2
  23. Crystal structure of (E)-1-(2-nitrophenyl)-N-(o-tolyl)methanimine, C14H12N2O2
  24. Crystal structure of 4′-amino-3′,5′-diisopropyl-(1,1′-biphenyl)-4-carbonitrile, C19H22N2
  25. The crystal structure of poly[bis(N,N-dimethylformamide-κ1O)-tetrakis(μ2-cyanido-κ2C:N)dinickel(II)], C10H14N6O2Ni2
  26. Crystal structure of rac-trans-N,N′-bis(3-bromo-5-chlorosalicylidene)-1,2-cyclohexanediamine, C20H18Br2Cl2N2O2
  27. Crystal structure of rac-trans-N,N′-bis(3,5-dibromosalicylidene)-1,2-cyclohexanediamine, C20H18Br4N2O2
  28. The crystal structure of (dichromato-κ2O,O′)bis(1,10-phenanthroline-κ2N,N′)nickel(II), C12H16N4O7Cr2Ni
  29. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridozincate(II) monohydrate, C10H18Cl4ZnN2O
  30. Crystal structure of bis(μ2-azido-k2N,N)-bis(2-amino-1-(N-(3-bromosalicylaldiminato))ethane)-dicopper(II), C20H18Br4N2O2
  31. Crystal structure of (η6-1-methyl-4-isopropylbenzene)-[5-bromo-2-(2-pyridyl)phenyl-κ2C,N]-chloro-ruthenium(II), C21H21BrClNRu
  32. Crystal structure of N-(methyl(oxo)(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-λ6-sulfanylidene)cyanamide, C10H10F3N3OS
  33. Crystal structure of 6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromo-4-chlorophenolato-κ4N,N′,O,O′)nickel(II), C20H16Br2Cl2NiN2O2
  34. Redetermination of the crystal structure of catena-poly[aqua-(1,10-phenanthroline-κ2N,N′)-(μ2-tetraoxidomolybdato(VI)-κ2O:O′)manganese(II) monohydrate, C12H12N2O6MoMn
  35. The crystal structure tetrakis(μ2-o-chlorobenzoato-κ2O:O′)-bis(methanol-κ1O)dirhodium(II), C30H24Cl4O10Rh2
  36. Crystal structure of bis(2,3-diphenyltetrazolidine-5-thione-κ1S)-(nitrato-κ1O)-(nitrato-κ2O,O′)lead(II), C26H20N10O6S2Pb
  37. Crystal structure of bis(3-bromo-N-(1-(3-methylpyrazin-2-yl)ethylidene)benzohydrazonato-κ3O,N,N′)cadmium(II) hemihydrate, C28H25N8O2.5Br2Cd
  38. Crystal structure of catena-poly[tetrakis(μ2-trifluoroacetato-κ2O:O′)(μ2-2,5-dimethylpyrazine-κ2N,N′)dicopper(II)], C7H4CuF6NO4
  39. The crystal structure of catena-poly[bis[3-azoniapentane-1,5-diammonium][bis(μ4-oxo)-tetrakis(μ3-oxo)-heptakis(μ2-oxo)-tetradecaoxo-octa-molybdenum] dihydrate], (C8H36N6O29Mo8)n
  40. Crystal structure of tetraaqua-bis(2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κO)-nickel(II)—diaqua-bis(2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-nickel(II), C28H24Cl12N4Ni2O18
  41. The crystal structure of bis(2-hydroxypyrimidinium) pentachloridobismuthate(III), (C4N2H5O)2BiCl5
  42. The crystal structure of catena-poly[(μ2-4,4′-dipyridine-κ2N,N′)-bis(3,5,6-trichloropyridine-2-oxyacetato-κO)-bis(ethanol-κO)nickel(II)], C28H26Cl6N4NiO8
  43. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3,5-bis(4-fluorobenzylidene)piperidin-4-one-dichloromethane (1/1), C26H20Cl3F2NO3S
  44. The crystal structure of 5-bromopicolinic acid monohydrate, C6H6BrNO3
  45. The crystal structure of 2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-8H-indeno[1,2-d]thiazole, C25H17BrFN3S
  46. The crystal structure of catena-poly[(μ2-2-((3-bromo-2-oxidobenzylidene)amino)acetato-κ4O,N,O′:O′′)-(dimethylformamide-κ1O)]zinc(II), C12H13N2O4BrZn
  47. Crystal structure of aqua-azido-κ1N-(6,6′-((propane-1,3-diylbis(azanylylidene))bis(methanylylidene))bis(3-bromophenolato)-κ4N,N′,O,O′iron(III), C17H16Br2FeN5O3
  48. The crystal structure of tris(1-ethylimidazole-κ1N)-(sulfato-κ2O,O′)vanadium(IV), C15H24N6O5SV
  49. Crystal structure of (E)-3-methoxy-N′-(1-(pyridin-2-yl)ethylidene)benzohydrazide, C15H15N3O2
  50. Crystal structure of dichloro-bis-(1-butyl-1H-benzo[d]imidazole)-nickel(II), C22H28Cl2N4Ni
  51. The crystal structure of 2-(2,3-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one, C17H14O5
  52. The crystal structure of 5-(2-(4-fluorophenyl)hydrazono)-4-methyl-2-((3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazono)-2,5-dihydrothiazole dimethylformamide monosolvate, C30H25FN10S⋅C3H7NO
  53. The crystal structure of 1,8-bis(pyridin-4-ylethynyl)anthracene-1,2,4,5-tetrafluoro-3,6-diiodobenzene (2/1), C62H32F4I2N4
  54. The crystal structure of 3,6-di-tert-butyl-1,8-diiodo-9-methyl-9H-carbazole, C21H25I2N
  55. The crystal structure of 8-((4-chlorophenylamino)methylene)-6,10-dioxaspiro[4.5]decane-7,9-dione, C15H14ClNO4
  56. The crystal structure of catena-poly[oktaaqua-bis(μ2-4,4′-ethene-1,2-diyldipyridine-κ2N:N′)-(μ2-3,3′-(1-oxidodiazene-1,2-diyl)diphthalato-κ2O:O′)dicobalt(II)] dihydrate, C28H36N4O19Co2
  57. Crystal structure of (E)-1-(2-cyano-3-oxo-1-phenylprop-1-en-1-yl)-3,7-diphenylindolizine-6-carbonitrile, C31H19N3O
  58. Crystal structure of 1,1′-bis(diphenylphosphino)ferrocene-(1,1′-bis(diphenylphosphino)ferrocene-κ2P,P′)-(O-isobutyl sulfurodithioito-κ2S,S′)copper(I), C39H37CuFeOP2S2
  59. Crystal structure of poly[(5-bimethylamino-1-naphthalenesulfonato-κO)-(μ3-hexamethylenetetramino-κ3N:N′:N′′)silver(I)] dihydrate, C36H52Ag2N10O8S2
  60. Crystal structure of poly[μ2-diaqua-(μ2-2-amino-4,5-dicyano-κ2N:N′-imidazol-1-ide)sodium(I)], C5H6N5O2Na
  61. Crystal structure of (1,3-propanediamine-κ2N,N′)(N-(3-aminopropyl)-α-methyl aspartato-κ4N,N′,O,O′)cobalt(III) chloride, C11H24ClCoN4O4
  62. Crystal structure and anti-inflammatory activity of (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one-dichloromethane (1/1), C26H20Cl2F3NO3S
  63. Crystal structure of (S)-(+)-1-cyclohexylethylaminium chloride, C8H18NCl
  64. The crystal structure of tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(o-pyridyl)imidazoline-1-oxyl 3-oxide-κ2N,O)yttrium(III), C24H32N9O13Y
  65. Hydrogen bonding versus packing effects in the crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetraiodidozincate(II), C10H16I4ZnN2
  66. Dimerization of 2-[(2-((2-aminophenyl)thio)phenyl)amino]-cyclohepta-2,4,6-trien-1-one through hydrogen bonding, C19H16N2OS
  67. Crystal structure of 1-(4-chloro-phenyl)-7-ethoxyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C18H12ClF2NO4
  68. Crystal structure of 7-ethoxy-6,8-difluoro-4-oxo-1-pyridin-2-ylmethyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H14F2N2O4
  69. Crystal structure of octahydro-7aR,8′R-dimethylspiro[isobenzofuran-4(1H), 4′ (3′H)-[1H-7,9a]methanocyclohepta[c]pyran]-1′,3, 9′ (3aH,4′aH)-trione, C20H26O5
  70. Crystal structure of bis(5-ethoxy-2-(((1-hydroxy-2-methyl-3-oxidopropan-2-yl)imino)methyl)phenolato-κ3N,O,O’)manganese(IV) – methanol (1/1), C27H38MnN2O9
  71. Crystal structure of 8a,8a′′-oxybis(8aH-8,9-dioxa-3a1λ4-aza-8aλ4-borabenzo[fg]tetracene), C34H22B2N2O5
  72. Crystal structure of bromido-triphenyl-(triphenylarsine oxide-κO)tin(IV), C36H30AsBrOSn
  73. Crystal structure of catena-poly[chlorido-(μ2-formato-κ2O:O′)-(1,10-phenathroline-κ2N,N′)copper(II)], C26H18Cl2Cu2N4O4
  74. The crystal structure of poly[(μ10-5-carboxyisophthalato-κ10O)disodium], C9H4Na2O6
  75. The crystal structure of 3,5-difluoroisonicotinic acid, C6H3F2NO2
  76. The crystal structure of ethyl-1-(N-(adamantan-1-yl)-carbamothioyl)piperidine-4-carboxylate, C19H30N2O2S
  77. Crystal structure of 5-methyl-3-phenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C19H21NO2S
  78. Crystal structure of bis((3-chlorosalicylidene)-ethylenediaminato-κ4N,N′,O,O′)nickel (II), C16H12Cl2NiN2O2
  79. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-4-hydroxybenzohydrazide — dihydrofuran-2(3H)-one (1/1), C18H17ClN2O5
  80. Crystal structure of bis((3-bromosalicylidene)-ethylenediaminato-κ4N,N′,O,O′) nickel (II), C16H12Br2NiN2O2
  81. Crystal structure of trimethylsulfoxonium tetrachloridocobaltate(II) [(CH3)3SO]2CoCl4
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