Home Physical Sciences Crystal structure of 7-ethoxyl-6,8-difluoro-4-oxo-1-phenyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H13F2N1O4
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Crystal structure of 7-ethoxyl-6,8-difluoro-4-oxo-1-phenyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H13F2N1O4

  • Jian-Xiong Huang , Cui-Xin Huang , Guo-Ping Huang , Yuan-Zhen Xiong EMAIL logo and Jian-Ping Huang ORCID logo EMAIL logo
Published/Copyright: February 12, 2020
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 3

Abstract

C18H13F2NO4, triclinic, P1̄ (no. 2), a = 7.9002(13) Å, b = 9.9371(16) Å, c = 10.6852(17) Å, α = 101.390(2)°, β = 93.169(2)°, γ = 104.901(2)°, V = 789.7(2) Å3, Z = 2, Rgt(F) = 0.0567, wRref(F2) = 0.1223, T = 296(2) K.

CCDC no.: 1978259

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:Colourless block
Size:0.17 × 0.15 × 0.13 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.12 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:27.6°, 99%
N(hkl)measured, N(hkl)unique, Rint:7108, 3570, 0.020
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2540
N(param)refined:241
Programs:Bruker [1], SHELX [2], [3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
C10.4506(2)0.9283(2)0.22163(18)0.0471(4)
C20.3893(3)0.9929(2)0.3322(2)0.0549(5)
C30.4781(3)1.1266(2)0.4043(2)0.0576(5)
C40.6346(3)1.1962(2)0.3637(2)0.0602(5)
C50.7006(3)1.1387(2)0.2587(2)0.0591(5)
H50.80621.18860.23520.071*
C60.6092(2)1.0036(2)0.18536(19)0.0486(4)
C70.6816(3)0.9439(2)0.0716(2)0.0527(5)
C80.5830(3)0.8058(2)0.00262(19)0.0521(5)
C90.4304(3)0.7387(2)0.0438(2)0.0551(5)
H90.36910.6485−0.00360.066*
C100.6395(3)0.7308(3)−0.1160(2)0.0659(6)
C110.1959(2)0.7050(2)0.17521(19)0.0496(5)
C120.0408(3)0.7171(3)0.1228(3)0.0711(7)
H120.03940.78370.07290.085*
C13−0.1147(3)0.6279(3)0.1457(3)0.0766(7)
H13−0.22180.63490.11090.092*
C14−0.1135(3)0.5302(2)0.2182(2)0.0649(6)
H14−0.21900.47220.23430.078*
C150.0434(3)0.5179(3)0.2671(3)0.0752(7)
H150.04450.44960.31530.090*
C160.2005(3)0.6056(2)0.2460(2)0.0660(6)
H160.30760.59720.27950.079*
C17a0.3312(7)1.2929(8)0.5078(5)0.116(2)
H17Aa0.35571.36280.58860.139*
H17Ba0.37381.34190.44090.139*
C17Bb0.2551(17)1.1689(19)0.5515(14)0.084(6)
H17Cb0.26331.21210.64210.101*
H17Db0.19581.06810.53970.101*
C180.1513(7)1.2320(7)0.4809(5)0.176(2)
H18A0.12551.17360.39540.265*
H18B0.09231.30590.48730.265*
H18C0.11131.17420.54130.265*
F10.24205(18)0.92385(14)0.37377(14)0.0829(5)
F20.7215(2)1.32612(14)0.43496(14)0.0861(5)
N10.3622(2)0.79323(17)0.14763(16)0.0513(4)
O10.7907(2)0.7983(2)−0.15055(17)0.0796(5)
H10.834(4)0.889(4)−0.090(3)0.119*
O20.5548(2)0.6152(2)−0.17739(18)0.0904(6)
O30.8214(2)1.01177(18)0.03759(16)0.0755(5)
O40.4248(2)1.18338(19)0.51602(16)0.0793(5)

  1. aOccupancy: 0.778(8), bOccupancy: 0.222(8).

Source of material

To a stirred solution of 6,7,8-trifluoro-4-oxo-1-phenyl-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (34.7 g, 0.1 moL) in ethanol (170 mL) was added sodium hydroxide (4.0 g, 0.1 moL), and then the reaction mixture was refluxed for about 0.5 h. After the reaction (monitored by TLC), the ethanol was distillated under reduced pressure to give a crude product. The crude product was poured into water (30 mL) and extracted with EtOAc (50 mL * 3). The EtOAc solvent was evaporated to provide the title compound in 85.3% yield. 1H NMR (400 MHz, CDCl3) δ 1.35–1.39 (t, J = 8.0 Hz, 3 H, CH3), 4.28–4.33 (q, J = 8.0, 12.0 Hz, 2 H, OCH2), 7.40–7.58 (m, 5 H, PhH), 8.05–8.08 (d, J = 12.0 Hz, 1 H, ArH), 8.63 (s, 1 H, NCH), 14.40 (br, 1 H, COOH) ppm. 13C NMR (100 MHz, CDCl3) δ = 176.04, 165.27, 154.50, 151.79, 149.81, 145.98, 143.50, 142.33, 129.45, 129.19, 129.08, 127.25, 124.92, 120.58, 107.56, 70.35, 14.72 ppm.

Experimental details

All H atoms were included in calculated positions and refined as riding atoms, with O—H = 0.82 Å with Uiso (H) = 1.2 Ueq (O), C—H = 0.93–0.98 Å) with Uiso(H) = 1.2–1.5 Ueq(C) [3].

Comment

Quinolones are synthetic antibiotics, which are a very important broad-spectrum antibiotic and the most important breakthrough in the synthesis of antibiotics after sulfonamines [5], [6], [7], [8]. Quinolones have been widely used in clinic since the advent of naphthalic acid in the 1960s. Due to the characteristics of wide antibacterial spectrum, strong antibacterial activity, convenient administration and no cross resistance with commonly used antibiotics, quinolones have been popularized rapidly in clinic, and become the key drug in the development, production and application in the world [9]. However, quinolones have been used or even abused for a long time, and bacteria have become resistant to some quinolones. Therefore, it is urgent to develop new quinolones effective against drug-resistant bacteria [10]. Recently, an expedient and high-yielding method for the synthesis of fluoroquinolones is explored in our group, and single crystals of several key intermediates are achieved. Herein, we report the synthesis and crystal structure of a key intermediate 7-ethoxyl-6,8-difluoro-4-oxo-1-phenyl-1,4-dihydro-quinoline-3-carboxylic acid, which provides a more efficient synthesis and a more comprehensive understanding for the synthesis of such compounds.

In the molecule of the title compound bond lengths and angles are very similar to those given in the literature for dimethyl 4-oxo-1-phenyl-1,4-dihydroquinoline-2,3-dicarboxylate [11], [12]. The molecule consists of two moieties: quinoline and benzene. The benzene ring is connected to the nitrogen atom (N1) of quinoline ring. The atoms of quinoline and benzene ring are coplanar, and the dihedral angle of quinoline ring and benzene ring is 88.28(8)°.

Acknowledgements

X-ray data were collected at Instrumental Analysis Center Nanchang Hangkong University, Nanchang, 330063, People’s Republic of China. This study was supported by grants from Natural Science Foundation of Science and Technology Department of Jiangxi Province (No. 20151BBF60081; 20171BBE50027; 20171BBG70029), Natural Science Foundation of Education Department of Jiangxi Province (No. GJJ170275), Natural Science Foundation of Nanchang City (No. 2014HZZC07, 2018CXTD014), and Natural Science Foundation of Jiangxi Agriculture University (No. 09004634; 09005194; 201910410043).

References

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Received: 2019-12-05
Accepted: 2020-01-16
Published Online: 2020-02-12
Published in Print: 2020-04-28

©2020 Jian-Xiong Huang 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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  77. Crystal structure of (E)-4-hydroxy-3-((5-phenyl-1,3,4-oxadiazol-2-yl)thio)pent-3-en-2-one, C13H12N2O3S
  78. The crystal structure of (2,3-dioxo-5,6:13,14-dibenzo-9,10-benzo-1,4,8,11-7, 11-diene-κ4N,N′,N′′,N′′′)-nickel(II), Ni(C22H14N4O2)
  79. Crystal structure of 3-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-ylthio)-propanoic acid, C15H17N3O4S
  80. The crystal structure of dichlorobis(2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl) palladium(II)-dichloroform, C68H100Cl8P2Pd
  81. Crystal structure and antimicrobial properties of (1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium(I) pentaiodide, C16H32CsI5O8
https://doi.org/10.1515/ncrs-2019-0885
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of catena-poly[(μ2-3-(benzo[d]thiazol-2-yl)-5-carboxybenzoato-κ2N:O)silver(I)], C15H8AgNO4S
  3. Crystal structure of bis(4-phenylpiperazin-1-ium) bis(2-(4-phenylpiperazin-1-yl)succinato-κ2O,O′)copper(II) tetrahydrate, C48H70CuN8O12, [C10H14N2]2[Cu(C14H17N2O4)2] ⋅ 4 H2O
  4. Crystal structure of triaqua-bis(2-(6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)-1-(2-oxo-2,5-dihydrofuran-3-yl)ethane-1-sulfonato-κ2O,O′)calcium(II) – ethanol (1/2), C44H76CaO19S2
  5. The crystal structure of ethyl 5-(4-(diphenylamino)phenyl)thiophene-2-carboxylate, C25H21NO2S
  6. The crystal structure of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine, C7H6BrN5
  7. The crystal structure of (E)-5-chloro-2-hydroxy-N′-(2-hydroxy-4-methoxybenzylidene)benzohydrazide, C15H13ClN2O4
  8. The crystal structure of (2Z,2′Z)-N′,N′′′′-(pyridine-2,6-dicarbonyl)dipicolinohydrazonamide, C19H17N9O2
  9. Photochromic properties and crystal structure of 3,3′-(perfluorocyclopent-1-ene-1,2-diyl)bis(5-(4-(azidomethyl)phenyl)-2-methylthiophene), C29H20F6N6S2
  10. Crystal structure of aqua-dichlorido-(4-(((3-ethoxy-2-oxidobenzylidene)hydrazono)(oxido)methyl)pyridin-1-ium-κ3N,O,O′)iron(III), C15H16Cl2N3O4Fe
  11. Crystal structure of catena-poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)-bis(2,3,4,5-tetrabromo-6-carboxybenzoato-κ1O)-nickel(II)], C26H14Br8NiN2O10
  12. Crystal structure of diethanol-κ1O-bis(μ2-N-((2-oxidonaphthalen-1-yl)methylene)pyrazine-2-carbohydrazonato-κ5N,O,O′:O′:N′)-bis(nitrato-κ2O,O′)dieuropium(III), C36H32N10O12Eu2
  13. The crystal structure of 2-aminoisophthalic acid, C8H7NO4
  14. Crystal structure of (E)-2-(4-((3,4-difluorobenzyl)oxy)styryl)-4,6-dimethoxybenzaldehyde, C24H20F2O4
  15. Crystal structure of 2-benzoylpyrene, C23H14O
  16. Crystal structure of chlorido-(η6-p-cymene)-(N-(2-fluorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) – acetone (1/1), C22H23ClN2F7OPRu
  17. The crystal structure of 2-bromoisonicotinic acid, C6H4BrNO2
  18. Crystal structure of 1,3,5,7-tetraphenyl-8-(N-phenylformamido)-2-oxa-5-azabicyclo[4.2.0]oct -3-en-7-yl benzoate, C44H34N2O4
  19. Synthesis and crystal structure of 4-(3-acetyl-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazol-2-yl)-7-(diethylamino)-2H-chromen-2-one, C21H21N3O4S
  20. Crystal structure of poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)-(μ2-3,4,5,6-tetrafluorophthalato-κ2O:O′)nickel(II)], C18H12F4NiN2O6
  21. Crystal structure of 4-hydroxynaphtho[2,3-b]benzofuran-6,11-dione, C16H8O4
  22. The crystal structure of 3,10-bis(4-methoxyphenyl)-6,12-dibenzyl-2,9-acetyl-6,12-diazapentacyclo[6.3.1.02,7.04,11.05,9]dodecane – acetone (1/1), C45H48N2O5
  23. The crystal structure of (E)-2-(((2-(1H-indol-3-yl)ethyl)iminio)methyl)-6-bromophenolate, C17H15N2BrO
  24. Crystal structure of catena-poly[diaqua-(μ2-oxalyl dihydrazide-κ4N,O:N′,O′)-bis(μ2-pyridine-2,3-dicarboxylato-κ3N,O,O′)dicadmium(II)] hexahydrate, C16H28O18N6Cd2
  25. Crystal structure of poly[tetra-(μ4-naphthalene-1,8-dicarboxylato-κ4O:O,O′: O′′:O′′,O′′′)-(μ4-oxo-κ4O:O:O:O) penta-lead(II)], C48H24O17Pb5
  26. Crystal structure of 5H-dibenzo[c,f][1,5]oxabismocin-12 (7H)-yl acetate, C16H15O3Bi
  27. The crystal structure of 2-(4-chloro-6-nitrophenyl)-1-(4-chloro-3-nitrophenyl)diazene 1-oxide, C12H6Cl2N4O5
  28. Crystal structure of bis(3-methyl-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-κ3O,N,N′)nickel(II), C28H26N8O2Ni
  29. Crystal structure of 3,10-bis(4-chlorophenyl)-6,12-dibenzyl-2,9-acetyl-6,12-diazapentacyclo[6.3.1.02,7.04,11.05,9]-dodecane, C40H36Cl2N2O2
  30. Crystal structure of bis[(μ2-4⋯O,O′:O′)-(4-hydroxybenzoato-κ2O,O′)-(1,10-phenanthroline-κ2N,N′)]-di-lead(II)μ-4-hydroxybenzoato-κ3O,O′:O′;κ3O,O′:O′-bis-[(4-hydroxybenzoato-κ2O,O′)bis(1,10-phenanthroline-κ2N,N′)di-lead(II)] monohydrate, C52H36N4O12Pb2 ⋅ H2O
  31. Crystal structure of poly[diaqua-(μ3-3,4,5,6-tetrafluoro-phthalato-κ3O:O′:O′′)-(μ2-1,2-bis(4-pyridyl)ethene-κ2N:N′)cobalt(II)], C14H9CoF4NO6
  32. Crystal structure of 7-hydroxy-4-phenyl-2H-chromen-2-one, C15H10O3
  33. Crystal structure of 3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione 4-hydroxybenzoic acid, C20H24N4O6
  34. Crystal structure of catena-poly[(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)-bis(nitrato-κ1O)zinc(II)], C17H16N6O7Zn
  35. The crystal structure of diaqua-bis(6-aminopicolinato-κ2N,O)magnesium(II), C12H14O6N4Mg
  36. Crystal structure of (pyridine-2-carboxamide-κ2N,O)-[tris((1H-benzo[d]imidazol-2-yl)methyl)amine-κ4N,N′,N′′,N′′′]nickel(II) diperchlorate — methanol (1/3), C33H39Cl2N9NiO12
  37. Crystal structure of catena-poly[diaqua-bis(3-(4-trifluoromethyl-phenyl)-acrylato-κO1)-(μ2-1,4-bis(1-imidazolyl)benzene-κ2N3:N3′)cobalt(II)], C32H26CoF6N4O6
  38. Crystal structure of (E)-3-(2-(2-hydroxy-4-methoxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate monohydrate, C22H25NO5S⋅H2O
  39. The crystal structure of bis(N-oxy-2-(1H-tetrazol-1-yl) acetamide κ2O,O′)-diaqua-zinc(II), C6H12ZnN10O6
  40. Crystal structure of (E)-4-((4-chlorophenylimino)methyl)pyridinium 3,5-dinitrobenzoate, C19H13ClN4O6
  41. Crystal structure of dichlorido-bis((E)-2-((pyridin-4-ylmethylene)amino)phenol)zinc(II), C24H20Cl2N4O2Zn
  42. Crystal structure of cyclo-[tetrachlorido-bis(μ2-p-xylylenediamine-κ2N:N′)dipalladium(II)] dimethyl sulfoxide solvate, C20H36Cl4N4O2Pd2S2
  43. Crystal structure of 4-(3-fluorophenyl)-7-hydroxy-2H-chromen-2-one, C15H9FO3
  44. Crystal structure of (E)-2-((2-(pyrimidin-2-yl)hydrazono)methyl)quinolin-1-ium perchlorate – methanol (1/1), C15H16N5O5Cl
  45. The crystal structure of bis(N-(amino(pyridin-2-yl)methylene)-5-chloro-2-hydroxybenzohydrazonato-κ3N,N′,O)zinc(II) – methanol (2/5), C57H60Cl2N16O13Zn2
  46. Synthesis and crystal structure of 4,4′-di(4-pyridyl)-6,6′-di(tert-butyl)-2,2′-[propylenedioxybis(nitrilomethylidyne)]diphenol, C35H40N4O4
  47. Crystal structure of (3E,3′E)-3,3′-((1,3,4-thiadiazole-2,5-diyl)bis(sulfanediyl))bis(4-hydroxy-4-phenylbut-3-en-2-one), C22H18N2O4S3
  48. Crystal structure of (N-benzyl-N-methyl-dithiocarbamato-κ2S,S′)di(4-chlorobenzyl)chloridotin(IV), C23H22Cl3NS2Sn
  49. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) sodium bromide hydrate, [Na(18-crown-6)]Br ⋅ H2O, C12H26BrNaO7
  50. Crystal structure of 7-ethoxyl-6,8-difluoro-4-oxo-1-phenyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H13F2N1O4
  51. Crystal structure of chlorido (2-(4-ethylphenyl)pyrimidine-k2C,N)(triphenylphosphane-kP) palladium(II), C30H26ClN2PPd
  52. Crystal structure of 18-crown-6 – 1,4-diiodotetrafluorobenzene – acetonitrile (1/1/2), C22H30F4I2N2O6
  53. Crystal structure of diisobutyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C16H24O6
  54. Crystal structure of poly[[tris(μ2-cis-1,2-cyclohexanedicarboxylato)-κ2O, O′]-bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N, N′,N′′]-trizinc(II)] – water (1/20), C60H106N12O32Zn3
  55. The synthesis and crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxamide–tetrahydrofuran (1/1), C16H14N4Cl2F6O3S
  56. Crystal structure of dimethylbis(diisopropyldithiocarbamato-κ2S,S′)tin(IV), C16H34N2S4Sn
  57. Crystal structure of diisopropyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C14H20O6
  58. The synthesis and crystal structure of ethyl (E)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-((2-methoxybenzylidene)amino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C22H15N3Cl2F6O4S
  59. The crystal structure of a matrine derivative, 13-(methylamine-1-yl) carbodithioate matrine, C17H27N3OS2
  60. Crystal structure of bis(2-hydroxy-6-((phenylimino)methyl)phenolato-κ2N,O)copper(II), C26H20CuN2O4
  61. The crystal structure of 2-p-fluorophenyl-5-dihydroxymethyl-1,3,4-oxadiazole, C9H7FN2O3
  62. Crystal structure of dichloridobis(4-chlorophenyl-κC1)(1,10-phenanthroline-κ2N,N′)tin(IV), C24H16Cl4N2Sn
  63. Crystal structure of bis{bromido-triphenyltin(IV)}(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′), C46H38Br2N2O2Sn2
  64. Crystal structure of 2-(5-chloro-quinolin-8-yloxy)-N-quinolin-8-yl-acetamide, C20H14N3O2Cl
  65. Crystal structure of bis(N-(1-(3-ethylpyrazin-2-yl)ethylidene)-3-hydroxy-2-naphthohydrazonato-κ3N,N′,O)cobalt(II) — dimethylformamide (1/1), C41H41N9O5Co
  66. Crystal structure of bis[2-(1-(3-ethylpyrazin-2-yl)ethylidene)-1-tosylhydrazin-1-ido-κ3-N,N′,O]copper(II), C30H34N8O4S2Cu
  67. Crystal structure of (2-p-tolylpyrimidine-κ2C,N)(triphenylphosphane-κP) palladium(II), C29H24ClN2PPd
  68. Halogen bonding in crystal structure of bis(1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium triiodide, C16H32CsI3O8
  69. The synthesis and crystal structure of N-(3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazol-5-yl)-2-phenylacetamide, C20H10N4Cl2F6O2S
  70. The crystal structure of 4-(trifluoromethyl)nicotinic acid, C7H4F3NO2
  71. Crystal structure of 3-(2-methylbenzyl)thiazolidin-2-one, C11H13ONS
  72. The crystal structure of 2,2,2-trifluoro-1-(isoquinolin-1-yl)ethane-1,1-diol, C11H8F3NO2
  73. The crystal structure of 3-bromoisonicotinic acid, C6H4BrNO2
  74. The crystal structure of 5-nitropicolinic acid monohydrate, C6H6N2O5
  75. The crystal structure of 3-(4-hydroxybenzyl)-1,5-dioxaspiro[5.5]undecane-2,4-dione, C16H18O5
  76. Crystal structure of [[Mo3Se7(S2CNEt2)3]2(μ-Se)] ⋅ 2(C6H4Cl2), C42H68Cl4Mo6N6S12Se15
  77. Crystal structure of (E)-4-hydroxy-3-((5-phenyl-1,3,4-oxadiazol-2-yl)thio)pent-3-en-2-one, C13H12N2O3S
  78. The crystal structure of (2,3-dioxo-5,6:13,14-dibenzo-9,10-benzo-1,4,8,11-7, 11-diene-κ4N,N′,N′′,N′′′)-nickel(II), Ni(C22H14N4O2)
  79. Crystal structure of 3-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-ylthio)-propanoic acid, C15H17N3O4S
  80. The crystal structure of dichlorobis(2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl) palladium(II)-dichloroform, C68H100Cl8P2Pd
  81. Crystal structure and antimicrobial properties of (1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium(I) pentaiodide, C16H32CsI5O8
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