Home Crystal structure of 3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione 4-hydroxybenzoic acid, C20H24N4O6
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Crystal structure of 3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione 4-hydroxybenzoic acid, C20H24N4O6

  • Peizhe Li , Lei Liu , Benyong Lou ORCID logo EMAIL logo and Hongbing Zhan
Published/Copyright: January 14, 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

C20H24N4O6, triclinic, P1̄ (no. 2), a = 8.2441(5) Å, b = 11.6409(6) Å, c = 12.0107(9) Å, α = 64.328(6)°, β = 70.778(6)°, γ = 86.678(4)°, V = 976.09(12) Å3, Z = 2, Rgt(F) = 0.0671, wRref(F2) = 0.1702, T = 100 K.

CCDC no.: 1971534

The crystal 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:Colorless block
Size:0.12 × 0.13 × 0.12 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.11 mm−1
Diffractometer, scan mode:SuperNova, ω-scans
θmax, completeness:29.5°, >84% (up to 25.3°, >99%)
N(hkl)measured, N(hkl)unique, Rint:8047, 4538, 0.026
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3586
N(param)refined:282
Programs:SHELX [1], [2], CrysAlisPRO [3]
Table 2:

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

xyzUiso*/Ueq
O11.1373(3)1.4219(2)−0.58966(19)0.0361(5)
O20.6617(2)0.86534(18)−0.45472(17)0.0262(4)
O30.6666(2)0.89051(17)−0.08677(17)0.0210(4)
O40.6466(2)0.88597(17)0.14372(18)0.0225(4)
O51.0450(2)1.31397(18)0.17545(19)0.0277(4)
O61.1294(2)1.38124(18)−0.04199(18)0.0247(4)
N10.6662(2)0.87322(19)−0.26895(19)0.0170(4)
N20.4885(3)0.7130(2)−0.2588(2)0.0195(5)
N30.3165(2)0.56413(19)−0.0393(2)0.0179(4)
N40.4017(2)0.64925(19)0.06879(19)0.0174(4)
C11.2065(4)1.3783(3)−0.3995(3)0.0323(7)
H1A1.3081411.439458−0.4610650.048*
H1B1.2431941.298254−0.3446700.048*
H1C1.1301021.414469−0.3435340.048*
C21.1115(3)1.3520(2)−0.4749(3)0.0234(6)
C30.9812(3)1.2359(2)−0.3988(2)0.0225(5)
H3A0.9045411.239100−0.3173520.027*
H3B1.0432251.158389−0.3729150.027*
C40.8704(3)1.2229(2)−0.4726(3)0.0241(6)
H4A0.9459191.212248−0.5501380.029*
H4B0.8155411.303161−0.5047450.029*
C50.7295(3)1.1106(2)−0.3903(2)0.0218(5)
H5A0.6570921.118669−0.3104190.026*
H5B0.6546181.114734−0.4413600.026*
C60.8018(3)0.9815(2)−0.3501(2)0.0200(5)
H6A0.8726040.972813−0.4299720.024*
H6B0.8782390.977906−0.3002990.024*
C70.6101(3)0.8323(2)−0.1333(2)0.0164(5)
C80.6080(3)0.8201(2)−0.3352(2)0.0189(5)
C90.4130(4)0.6566(3)−0.3208(3)0.0257(6)
H9A0.4384760.567172−0.2946250.038*
H9B0.4624090.704772−0.4164280.038*
H9C0.2876790.660014−0.2927200.038*
C100.4318(3)0.6666(2)−0.1250(2)0.0171(5)
C110.4890(3)0.7223(2)−0.0638(2)0.0163(5)
C120.4164(3)0.6694(2)0.1767(2)0.0216(5)
H12A0.3390010.6045830.2600970.032*
H12B0.3844790.7549230.1664950.032*
H12C0.5357150.6623200.1760970.032*
C130.3019(3)0.5569(2)0.0776(2)0.0191(5)
H130.2284290.4929990.1584590.023*
C140.7384(3)0.9901(2)0.1235(2)0.0170(5)
C150.7373(3)1.0035(2)0.2335(2)0.0182(5)
H150.6701300.9426740.3189180.022*
C160.8342(3)1.1055(2)0.2178(2)0.0182(5)
H160.8338321.1142610.2929380.022*
C170.8342(3)1.0812(2)−0.0021(2)0.0185(5)
H170.8330661.073480−0.0773920.022*
C180.9304(3)1.1825(2)−0.0159(2)0.0188(5)
H180.9963261.244164−0.1012660.023*
C190.9326(3)1.1959(2)0.0931(2)0.0176(5)
C201.0394(3)1.3018(2)0.0802(2)0.0200(5)
H40.651(5)0.885(4)0.065(4)0.064(12)*
H61.191(4)1.445(3)−0.042(3)0.044(10)*

Source of material

Pentoxifylline (278 mg, 1 mmol) and 4-hydroxybenzoic acid (138 mg, 1 mmol) were dissolved in ethanol (30 mL). The colorless block crystals were obtained after several days.

Experimental details

The structure was solved by direct methods and refined on F2 by full-matrix least-squares methods using the SHELX program package [1,2]. H atoms on C atoms were located geometrically with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C). H atoms bonded to O were located by difference maps and refined freely.

Discussion

Pentoxifylline, 3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione, is a cardiovascular drug which is formulated as sustained-release tablets [4]. Several cocrystals of pentoxifylline based on synthons between imidazole and carboxylic acids have been reported [5], [6]. There are four hydrogen-bond acceptors in molecular structure of pentoxifylline [7], which could result in various intermolecular interactions with different cocrystal formers. In this work, a cocrystal of pentoxifylline with 4-hydroxybenzoic acid, [C13H18N4 O3]. [C7 H6 O3], was studied.

The cocrystal crystallized in the triclinic P1̄ space group and contained one molecule of pentoxifylline and one molecule of 4-hydroxybenzoic acid in the asymmetric unit. There exist R22(7) synthon between the imidazole ring of pentoxifylline and the carboxyl group of 4-hydroxybenzoic acid (O6-H6⋯N3 = 2.718(3) Å; C13—H13⋯O5 = 3.168(3) Å, x − 1, y − 1, z). There also exist hydrogen-bonded interactions between the purine moiety of pentoxifylline and the hydroxyl group of 4-hydroxybenzoic acid (O4—H4⋯O3 = 2.696(3) Å; C17—H17⋯O3 = 3.333(3) Å). As a result, 4-hydroxybenzoic acid and pentoxifylline are linked parallel to each other into a 1D hydrogen-bonded chain along the [1 1 0] direction. The purine rings of pentoxifylline are almost coplanar with 4-hydroxybenzoic acid within the chain.

The other two hydrogen-bond acceptors (O1 and O2) of pentoxifylline are involved in different weak C—H⋯O interactions. The —C=O in side chain of pentoxifylline is involved in C—H⋯O interactions with the imidazole ring of pentoxifylline (C12—H12A⋯O1 = 3.314(3) Å; C13—H13⋯O1 = 3.394(3) Å, x − 1, y − 1, z + 1). There also exist C—H⋯O interactions between the phenyl ring of 4-hydroxybenzoic acid and the C=O of purine (C15—H15⋯O2 = 3.218(3) Å, x, y, z + 1). There exist pi-pi interactions between imidazole groups with a centroid–centroid distance of 3.428 Å. The purine ring is also involved in pi-pi interactions with the phenyl ring of 4-hydroxybenzoic acid with a centroid–centroid distance of 3.506 Å. As a result, the various weak intermolecular interactions engineer the hydrogen-bonded chains into a structure with a density of 1.417 g/cm3.

Acknowledgements

The authors are grateful to the support from the Natural Science Foundation of Fujian Province (2019J01758) and Research Projects of Minjiang University (MJY18003).

References

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Received: 2019-11-16
Accepted: 2019-12-12
Published Online: 2020-01-14
Published in Print: 2020-04-28

©2020 Peizhe Li et al., published by De Gruyter.

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

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  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-2019-0841
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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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